# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_11
_audit_block_doi                 10.5517/ccdc.csd.cc1k5v0l
_database_code_depnum_ccdc_archive 'CCDC 1435579'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/C7QI00727B 2018
_audit_update_record             
;
2015-11-06 deposited with the CCDC.	2024-07-03 downloaded from the CCDC.
;


_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H26 F6 N10 O6 S2 Yb, C F3 O3 S'
_chemical_formula_sum            'C25 H26 F9 N10 O9 S3 Yb'
_chemical_formula_weight         1050.78

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Yb Yb -0.3850 5.5486 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   11.3018(5)
_cell_length_b                   13.3845(6)
_cell_length_c                   14.5613(4)
_cell_angle_alpha                96.292(3)
_cell_angle_beta                 99.214(3)
_cell_angle_gamma                107.796(4)
_cell_volume                     2040.55(15)
_cell_formula_units_Z            2
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    11134
_cell_measurement_theta_min      3.0530
_cell_measurement_theta_max      26.9900

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.710
_exptl_crystal_F_000             1034
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.04
_exptl_absorpt_coefficient_mu    2.544
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.83124
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?

_diffrn_ambient_temperature      295(2)
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Eos
_diffrn_detector_area_resol_mean 16.1544
_diffrn_measurement_method       ω-scan
_diffrn_reflns_number            21875
_diffrn_reflns_av_unetI/netI     0.0420
_diffrn_reflns_av_R_equivalents  0.0385
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.054
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_full        24.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             7183
_reflns_number_gt                6382
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlis Pro (Agilent Technologies (2011))'
_computing_cell_refinement       'CrysAlis Pro (Agilent Technologies (2011))'
_computing_data_reduction        'CrysAlis Pro (Agilent Technologies (2011))'
_computing_structure_solution    'SIR92 (Altomare et al., 1993)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'Mercury (MacRae et al., 2009)'
_computing_publication_material  'SHELXL-2014 (Sheldrick, 2014)'

_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0830P)²+2.4190P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7183
_refine_ls_number_parameters     518
_refine_ls_number_restraints     177
_refine_ls_R_factor_all          0.0619
_refine_ls_R_factor_gt           0.0558
_refine_ls_wR_factor_ref         0.1628
_refine_ls_wR_factor_gt          0.1592
_refine_ls_goodness_of_fit_ref   1.305
_refine_ls_restrained_S_all      1.319
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000


# SQUEEZE RESULTS (APPEND TO CIF)
# Note: Data are Listed for all Voids in the P1 Unit Cell
# i.e. Centre of Gravity, Solvent Accessible Volume,
# Recovered number of Electrons in the Void and
# Details about the Squeezed Material
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.000 0.000 0.500 230 26 ' '
2 -0.013 0.077 0.017 11 1 ' '
3 0.014 0.919 0.982 10 1 ' '
_platon_squeeze_details          
;
;

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Yb1 Yb 0.35778(3) 0.70885(2) 0.72966(2) 0.04058(15) Uani 1 1 d . . . . .
N1A N 0.4281(7) 0.5593(5) 0.7730(5) 0.0478(15) Uani 1 1 d . . . . .
C2A C 0.5172(10) 0.5307(8) 0.7337(7) 0.067(3) Uani 1 1 d . . . . .
H2A H 0.5478 0.5668 0.6868 0.080 Uiso 1 1 calc R U . . .
C3A C 0.5638(10) 0.4541(8) 0.7577(7) 0.068(3) Uani 1 1 d . . . . .
H3A H 0.6261 0.4389 0.7298 0.082 Uiso 1 1 calc R U . . .
C4A C 0.5153(11) 0.3985(8) 0.8262(8) 0.072(3) Uani 1 1 d . . . . .
H4A H 0.5434 0.3434 0.8431 0.087 Uiso 1 1 calc R U . . .
C5A C 0.4280(10) 0.4239(7) 0.8682(7) 0.065(2) Uani 1 1 d . . . . .
H5A H 0.3964 0.3874 0.9145 0.078 Uiso 1 1 calc R U . . .
C6A C 0.3858(8) 0.5061(6) 0.8409(5) 0.0453(18) Uani 1 1 d . . . . .
N7A N 0.2973(7) 0.5340(6) 0.8815(5) 0.0536(17) Uani 1 1 d . . . . .
C71A C 0.2458(10) 0.4859(9) 0.9587(7) 0.077(3) Uani 1 1 d . . . . .
H71A H 0.2485 0.5410 1.0079 0.115 Uiso 1 1 calc R U . . .
H71B H 0.2956 0.4445 0.9834 0.115 Uiso 1 1 calc R U . . .
H71C H 0.1594 0.4406 0.9353 0.115 Uiso 1 1 calc R U . . .
N8A N 0.2526(6) 0.6062(5) 0.8430(5) 0.0492(16) Uani 1 1 d . . . . .
C9A C 0.1561(8) 0.6275(7) 0.8696(6) 0.053(2) Uani 1 1 d . . . . .
H9A H 0.1149 0.5940 0.9139 0.064 Uiso 1 1 calc R U . . .
C10A C 0.1192(8) 0.7066(7) 0.8249(6) 0.0511(19) Uani 1 1 d . . . . .
N11A N 0.0172(7) 0.7360(7) 0.8338(6) 0.068(2) Uani 1 1 d . . . . .
C11A C -0.0813(11) 0.6877(12) 0.8869(9) 0.098(4) Uani 1 1 d . . . . .
H11A H -0.1547 0.7082 0.8681 0.146 Uiso 1 1 calc R U . . .
H11B H -0.0484 0.7120 0.9533 0.146 Uiso 1 1 calc R U . . .
H11C H -0.1046 0.6115 0.8737 0.146 Uiso 1 1 calc R U . . .
C12A C 0.0181(9) 0.8116(9) 0.7811(8) 0.072(3) Uani 1 1 d . . . . .
H12A H -0.0403 0.8477 0.7735 0.086 Uiso 1 1 calc R U . . .
C13A C 0.1204(10) 0.8256(9) 0.7411(8) 0.075(3) Uani 1 1 d . . . . .
H13A H 0.1443 0.8743 0.7011 0.090 Uiso 1 1 calc R U . . .
N14A N 0.1832(7) 0.7587(6) 0.7674(5) 0.0540(17) Uani 1 1 d . . . . .
N1B N 0.4047(7) 0.8973(5) 0.7107(5) 0.0501(16) Uani 1 1 d . . . . .
C2B C 0.4565(11) 0.9717(8) 0.7851(7) 0.068(3) Uani 1 1 d . . . . .
H2B H 0.4736 0.9511 0.8434 0.082 Uiso 1 1 calc R U . . .
C3B C 0.4873(13) 1.0800(8) 0.7816(8) 0.088(4) Uani 1 1 d . . . . .
H3B H 0.5260 1.1313 0.8353 0.106 Uiso 1 1 calc R U . . .
C4B C 0.4578(15) 1.1071(9) 0.6955(8) 0.097(4) Uani 1 1 d . . . . .
H4B H 0.4769 1.1786 0.6900 0.116 Uiso 1 1 calc R U . . .
C5B C 0.4013(12) 1.0320(8) 0.6182(7) 0.077(3) Uani 1 1 d . . . . .
H5B H 0.3801 1.0513 0.5600 0.093 Uiso 1 1 calc R U . . .
C6B C 0.3751(8) 0.9250(7) 0.6265(6) 0.0486(19) Uani 1 1 d . . . . .
N7B N 0.3150(7) 0.8452(6) 0.5512(5) 0.0558(18) Uani 1 1 d . . . . .
C71B C 0.2869(12) 0.8617(9) 0.4516(7) 0.082(3) Uani 1 1 d . . . . .
H71D H 0.3086 0.8112 0.4113 0.123 Uiso 1 1 calc R U . . .
H71E H 0.3358 0.9326 0.4464 0.123 Uiso 1 1 calc R U . . .
H71F H 0.1981 0.8518 0.4330 0.123 Uiso 1 1 calc R U . . .
N8B N 0.2779(6) 0.7449(5) 0.5698(5) 0.0469(15) Uani 1 1 d . . . . .
C9B C 0.2215(8) 0.6640(7) 0.5036(6) 0.053(2) Uani 1 1 d . . . . .
H9B H 0.2016 0.6717 0.4409 0.064 Uiso 1 1 calc R U . . .
C10B C 0.1917(8) 0.5639(7) 0.5315(6) 0.0511(19) Uani 1 1 d . . . . .
N11B N 0.1340(7) 0.4672(6) 0.4761(5) 0.0573(18) Uani 1 1 d . . . . .
C11B C 0.1039(11) 0.4466(9) 0.3742(8) 0.078(3) Uani 1 1 d . . . . .
H11D H 0.1099 0.5121 0.3511 0.116 Uiso 1 1 calc R U . . .
H11E H 0.0192 0.3975 0.3527 0.116 Uiso 1 1 calc R U . . .
H11F H 0.1627 0.4166 0.3511 0.116 Uiso 1 1 calc R U . . .
C12B C 0.1175(9) 0.3937(7) 0.5368(7) 0.061(2) Uani 1 1 d . . . . .
H12B H 0.0793 0.3204 0.5195 0.073 Uiso 1 1 calc R U . . .
C13B C 0.1659(10) 0.4466(7) 0.6245(8) 0.066(2) Uani 1 1 d . . . . .
H13B H 0.1684 0.4158 0.6787 0.079 Uiso 1 1 calc R U . . .
N14B N 0.2123(7) 0.5554(6) 0.6225(5) 0.0551(17) Uani 1 1 d . . . . .
S1C S 0.6275(2) 0.7810(2) 0.6144(2) 0.0666(6) Uani 1 1 d . U . . .
O11C O 0.5176(5) 0.7273(5) 0.6511(4) 0.0521(14) Uani 1 1 d . U . . .
O12C O 0.6340(8) 0.8719(8) 0.5896(6) 0.111(3) Uani 1 1 d . U . . .
O13C O 0.7421(8) 0.7701(10) 0.6627(8) 0.124(4) Uani 1 1 d . U . . .
C1C C 0.5899(13) 0.6980(10) 0.4981(9) 0.085(3) Uani 1 1 d . U . . .
F11C F 0.4835(9) 0.6966(10) 0.4520(6) 0.147(4) Uani 1 1 d . U . . .
F12C F 0.6789(9) 0.7366(7) 0.4507(6) 0.125(3) Uani 1 1 d . U . . .
F13C F 0.5982(11) 0.6031(7) 0.5111(7) 0.141(4) Uani 1 1 d . U . . .
S1D S 0.5809(3) 0.7782(2) 0.94887(17) 0.0640(6) Uani 1 1 d . U . . .
O11D O 0.5033(6) 0.7867(5) 0.8619(4) 0.0590(15) Uani 1 1 d . U . . .
O12D O 0.6476(6) 0.7173(6) 0.9492(5) 0.081(2) Uani 1 1 d . U . . .
O13D O 0.5161(11) 0.7697(8) 1.0254(6) 0.111(3) Uani 1 1 d . U . . .
C1D C 0.6995(17) 0.9082(13) 0.9795(14) 0.122(5) Uani 1 1 d . U . . .
F11D F 0.7813(13) 0.9100(9) 1.0573(10) 0.226(7) Uani 1 1 d . U . . .
F12D F 0.7638(11) 0.9267(10) 0.9121(12) 0.195(6) Uani 1 1 d . U . . .
F13D F 0.6474(12) 0.9826(7) 0.9953(8) 0.160(4) Uani 1 1 d . U . . .
S1E S 0.8740(3) 0.3398(2) 0.8050(2) 0.0780(7) Uani 1 1 d . U . . .
O11E O 0.9682(15) 0.3468(13) 0.7520(11) 0.188(6) Uani 1 1 d . U . . .
O12E O 0.7553(11) 0.3177(9) 0.7454(9) 0.146(5) Uani 1 1 d . U . . .
O13E O 0.9151(11) 0.4098(10) 0.8907(9) 0.153(5) Uani 1 1 d . U . . .
C1E C 0.869(2) 0.2128(16) 0.8344(13) 0.150(6) Uani 1 1 d . U . . .
F11E F 0.7890(18) 0.1976(13) 0.9042(11) 0.247(8) Uani 1 1 d . U . . .
F12E F 0.9839(16) 0.2155(11) 0.8791(10) 0.219(7) Uani 1 1 d . U . . .
F13E F 0.8214(15) 0.1355(8) 0.7720(8) 0.191(6) Uani 1 1 d . U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Yb1 O11D 2.235(6) . ?
Yb1 O11C 2.255(5) . ?
Yb1 N14A 2.390(7) . ?
Yb1 N14B 2.402(7) . ?
Yb1 N1B 2.470(6) . ?
Yb1 N1A 2.475(6) . ?
Yb1 N8A 2.480(6) . ?
Yb1 N8B 2.512(6) . ?
N1A C6A 1.345(10) . ?
N1A C2A 1.364(11) . ?
C2A C3A 1.341(12) . ?
C2A H2A 0.9300 . ?
C3A C4A 1.391(14) . ?
C3A H3A 0.9300 . ?
C4A C5A 1.348(14) . ?
C4A H4A 0.9300 . ?
C5A C6A 1.397(12) . ?
C5A H5A 0.9300 . ?
C6A N7A 1.362(11) . ?
N7A N8A 1.353(9) . ?
N7A C71A 1.469(11) . ?
C71A H71A 0.9600 . ?
C71A H71B 0.9600 . ?
C71A H71C 0.9600 . ?
N8A C9A 1.313(10) . ?
C9A C10A 1.432(12) . ?
C9A H9A 0.9300 . ?
C10A N14A 1.313(11) . ?
C10A N11A 1.347(11) . ?
N11A C12A 1.334(14) . ?
N11A C11A 1.484(13) . ?
C11A H11A 0.9600 . ?
C11A H11B 0.9600 . ?
C11A H11C 0.9600 . ?
C12A C13A 1.348(14) . ?
C12A H12A 0.9300 . ?
C13A N14A 1.352(12) . ?
C13A H13A 0.9300 . ?
N1B C2B 1.308(12) . ?
N1B C6B 1.339(10) . ?
C2B C3B 1.393(14) . ?
C2B H2B 0.9300 . ?
C3B C4B 1.361(16) . ?
C3B H3B 0.9300 . ?
C4B C5B 1.347(15) . ?
C4B H4B 0.9300 . ?
C5B C6B 1.394(12) . ?
C5B H5B 0.9300 . ?
C6B N7B 1.366(11) . ?
N7B N8B 1.349(9) . ?
N7B C71B 1.490(11) . ?
C71B H71D 0.9600 . ?
C71B H71E 0.9600 . ?
C71B H71F 0.9600 . ?
N8B C9B 1.288(11) . ?
C9B C10B 1.401(12) . ?
C9B H9B 0.9300 . ?
C10B N14B 1.331(11) . ?
C10B N11B 1.356(11) . ?
N11B C12B 1.385(12) . ?
N11B C11B 1.443(13) . ?
C11B H11D 0.9600 . ?
C11B H11E 0.9600 . ?
C11B H11F 0.9600 . ?
C12B C13B 1.331(14) . ?
C12B H12B 0.9300 . ?
C13B N14B 1.394(12) . ?
C13B H13B 0.9300 . ?
S1C O12C 1.291(10) . ?
S1C O13C 1.427(9) . ?
S1C O11C 1.447(6) . ?
S1C C1C 1.831(13) . ?
C1C F11C 1.274(15) . ?
C1C F12C 1.319(13) . ?
C1C F13C 1.333(14) . ?
S1D O12D 1.267(8) . ?
S1D O13D 1.425(9) . ?
S1D O11D 1.458(6) . ?
S1D C1D 1.799(16) . ?
C1D F12D 1.31(2) . ?
C1D F13D 1.32(2) . ?
C1D F11D 1.336(17) . ?
S1E O13E 1.393(11) . ?
S1E O11E 1.399(12) . ?
S1E O12E 1.404(11) . ?
S1E C1E 1.784(19) . ?
C1E F13E 1.217(19) . ?
C1E F12E 1.35(2) . ?
C1E F11E 1.45(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O11D Yb1 O11C 88.3(2) . . ?
O11D Yb1 N14A 100.1(3) . . ?
O11C Yb1 N14A 150.7(2) . . ?
O11D Yb1 N14B 152.6(2) . . ?
O11C Yb1 N14B 95.3(2) . . ?
N14A Yb1 N14B 90.0(3) . . ?
O11D Yb1 N1B 80.2(2) . . ?
O11C Yb1 N1B 80.0(2) . . ?
N14A Yb1 N1B 74.0(2) . . ?
N14B Yb1 N1B 127.2(2) . . ?
O11D Yb1 N1A 78.2(2) . . ?
O11C Yb1 N1A 80.1(2) . . ?
N14A Yb1 N1A 129.0(2) . . ?
N14B Yb1 N1A 75.6(2) . . ?
N1B Yb1 N1A 150.9(2) . . ?
O11D Yb1 N8A 80.7(2) . . ?
O11C Yb1 N8A 142.5(2) . . ?
N14A Yb1 N8A 66.8(2) . . ?
N14B Yb1 N8A 80.0(2) . . ?
N1B Yb1 N8A 132.1(2) . . ?
N1A Yb1 N8A 62.6(2) . . ?
O11D Yb1 N8B 141.0(2) . . ?
O11C Yb1 N8B 73.7(2) . . ?
N14A Yb1 N8B 82.5(2) . . ?
N14B Yb1 N8B 65.3(2) . . ?
N1B Yb1 N8B 63.0(2) . . ?
N1A Yb1 N8B 129.8(2) . . ?
N8A Yb1 N8B 133.4(2) . . ?
C6A N1A C2A 116.5(7) . . ?
C6A N1A Yb1 121.4(5) . . ?
C2A N1A Yb1 121.9(5) . . ?
C3A C2A N1A 124.7(9) . . ?
C3A C2A H2A 117.6 . . ?
N1A C2A H2A 117.6 . . ?
C2A C3A C4A 117.4(9) . . ?
C2A C3A H3A 121.3 . . ?
C4A C3A H3A 121.3 . . ?
C5A C4A C3A 120.6(9) . . ?
C5A C4A H4A 119.7 . . ?
C3A C4A H4A 119.7 . . ?
C4A C5A C6A 118.8(9) . . ?
C4A C5A H5A 120.6 . . ?
C6A C5A H5A 120.6 . . ?
N1A C6A N7A 117.4(7) . . ?
N1A C6A C5A 122.0(8) . . ?
N7A C6A C5A 120.6(8) . . ?
N8A N7A C6A 115.9(6) . . ?
N8A N7A C71A 120.4(7) . . ?
C6A N7A C71A 123.6(7) . . ?
N7A C71A H71A 109.5 . . ?
N7A C71A H71B 109.5 . . ?
H71A C71A H71B 109.5 . . ?
N7A C71A H71C 109.5 . . ?
H71A C71A H71C 109.5 . . ?
H71B C71A H71C 109.5 . . ?
C9A N8A N7A 120.0(7) . . ?
C9A N8A Yb1 118.6(5) . . ?
N7A N8A Yb1 121.3(5) . . ?
N8A C9A C10A 114.5(7) . . ?
N8A C9A H9A 122.7 . . ?
C10A C9A H9A 122.7 . . ?
N14A C10A N11A 111.7(8) . . ?
N14A C10A C9A 122.3(7) . . ?
N11A C10A C9A 126.1(8) . . ?
C12A N11A C10A 106.8(8) . . ?
C12A N11A C11A 127.0(9) . . ?
C10A N11A C11A 126.1(10) . . ?
N11A C11A H11A 109.5 . . ?
N11A C11A H11B 109.5 . . ?
H11A C11A H11B 109.5 . . ?
N11A C11A H11C 109.5 . . ?
H11A C11A H11C 109.5 . . ?
H11B C11A H11C 109.5 . . ?
N11A C12A C13A 106.6(8) . . ?
N11A C12A H12A 126.7 . . ?
C13A C12A H12A 126.7 . . ?
C12A C13A N14A 110.5(10) . . ?
C12A C13A H13A 124.8 . . ?
N14A C13A H13A 124.8 . . ?
C10A N14A C13A 104.5(8) . . ?
C10A N14A Yb1 117.7(5) . . ?
C13A N14A Yb1 137.7(7) . . ?
C2B N1B C6B 119.2(7) . . ?
C2B N1B Yb1 119.1(6) . . ?
C6B N1B Yb1 121.6(5) . . ?
N1B C2B C3B 123.5(9) . . ?
N1B C2B H2B 118.3 . . ?
C3B C2B H2B 118.3 . . ?
C4B C3B C2B 116.7(10) . . ?
C4B C3B H3B 121.7 . . ?
C2B C3B H3B 121.7 . . ?
C5B C4B C3B 121.1(10) . . ?
C5B C4B H4B 119.5 . . ?
C3B C4B H4B 119.5 . . ?
C4B C5B C6B 119.3(10) . . ?
C4B C5B H5B 120.4 . . ?
C6B C5B H5B 120.4 . . ?
N1B C6B N7B 117.7(7) . . ?
N1B C6B C5B 120.3(8) . . ?
N7B C6B C5B 121.9(8) . . ?
N8B N7B C6B 116.8(7) . . ?
N8B N7B C71B 118.6(7) . . ?
C6B N7B C71B 124.6(7) . . ?
N7B C71B H71D 109.5 . . ?
N7B C71B H71E 109.5 . . ?
H71D C71B H71E 109.5 . . ?
N7B C71B H71F 109.5 . . ?
H71D C71B H71F 109.5 . . ?
H71E C71B H71F 109.5 . . ?
C9B N8B N7B 121.7(7) . . ?
C9B N8B Yb1 117.4(5) . . ?
N7B N8B Yb1 119.7(5) . . ?
N8B C9B C10B 116.3(8) . . ?
N8B C9B H9B 121.9 . . ?
C10B C9B H9B 121.9 . . ?
N14B C10B N11B 111.4(8) . . ?
N14B C10B C9B 120.7(8) . . ?
N11B C10B C9B 127.8(8) . . ?
C10B N11B C12B 106.0(7) . . ?
C10B N11B C11B 126.1(8) . . ?
C12B N11B C11B 127.8(8) . . ?
N11B C11B H11D 109.5 . . ?
N11B C11B H11E 109.5 . . ?
H11D C11B H11E 109.5 . . ?
N11B C11B H11F 109.5 . . ?
H11D C11B H11F 109.5 . . ?
H11E C11B H11F 109.5 . . ?
C13B C12B N11B 107.9(8) . . ?
C13B C12B H12B 126.1 . . ?
N11B C12B H12B 126.1 . . ?
C12B C13B N14B 109.4(9) . . ?
C12B C13B H13B 125.3 . . ?
N14B C13B H13B 125.3 . . ?
C10B N14B C13B 105.3(7) . . ?
C10B N14B Yb1 116.8(6) . . ?
C13B N14B Yb1 135.3(6) . . ?
O12C S1C O13C 117.4(6) . . ?
O12C S1C O11C 117.3(5) . . ?
O13C S1C O11C 113.0(5) . . ?
O12C S1C C1C 100.0(6) . . ?
O13C S1C C1C 105.5(7) . . ?
O11C S1C C1C 100.0(5) . . ?
S1C O11C Yb1 158.1(4) . . ?
F11C C1C F12C 109.1(12) . . ?
F11C C1C F13C 115.4(13) . . ?
F12C C1C F13C 104.6(9) . . ?
F11C C1C S1C 110.1(8) . . ?
F12C C1C S1C 109.7(10) . . ?
F13C C1C S1C 107.7(10) . . ?
O12D S1D O13D 110.9(6) . . ?
O12D S1D O11D 121.5(5) . . ?
O13D S1D O11D 112.9(5) . . ?
O12D S1D C1D 102.4(7) . . ?
O13D S1D C1D 104.4(9) . . ?
O11D S1D C1D 102.1(6) . . ?
S1D O11D Yb1 149.8(4) . . ?
F12D C1D F13D 110.3(15) . . ?
F12D C1D F11D 107.4(17) . . ?
F13D C1D F11D 109.5(16) . . ?
F12D C1D S1D 110.1(13) . . ?
F13D C1D S1D 111.1(13) . . ?
F11D C1D S1D 108.4(12) . . ?
O13E S1E O11E 113.9(9) . . ?
O13E S1E O12E 124.0(8) . . ?
O11E S1E O12E 110.4(10) . . ?
O13E S1E C1E 105.4(9) . . ?
O11E S1E C1E 95.3(11) . . ?
O12E S1E C1E 102.8(9) . . ?
F13E C1E F12E 111(2) . . ?
F13E C1E F11E 106(2) . . ?
F12E C1E F11E 105.8(16) . . ?
F13E C1E S1E 117.8(13) . . ?
F12E C1E S1E 110.7(16) . . ?
F11E C1E S1E 104.2(16) . . ?

_refine_diff_density_max         3.225
_refine_diff_density_min         -1.111
_refine_diff_density_rms         0.159

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_04
_database_code_depnum_ccdc_archive 'CCDC 1005950'
_audit_update_record             
;
2016-01-10 deposited with the CCDC.	2024-07-03 downloaded from the CCDC.
;


_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C25 H26 F9 N10 O9 S3 Sm'
_chemical_formula_sum            'C25 H26 F9 N10 O9 S3 Sm'
_chemical_formula_weight         1028.09

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Sm Sm -0.1638 3.4418 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x+1/2, y, z+1/2'
'x+1/2, -y, z'

_cell_length_a                   10.8093(5)
_cell_length_b                   17.0375(5)
_cell_length_c                   19.6847(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3625.2(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(1)
_cell_measurement_reflns_used    2260
_cell_measurement_theta_min      3.6200
_cell_measurement_theta_max      26.5470

_exptl_crystal_description       plate
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.884
_exptl_crystal_F_000             2036
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.1
_exptl_absorpt_coefficient_mu    1.904
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.36525
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(1)
_diffrn_radiation_wavelength     0.7107
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_detector_area_resol_mean 16.1544
_diffrn_measurement_method       ω-scan
_diffrn_reflns_number            8618
_diffrn_reflns_av_unetI/netI     0.0229
_diffrn_reflns_av_R_equivalents  0.0197
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         3.045
_diffrn_reflns_theta_max         26.575
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.909
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.909
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.653
_diffrn_reflns_point_group_measured_fraction_full 0.727
_reflns_number_total             4954
_reflns_number_gt                4899
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.392
_reflns_Friedel_fraction_max     0.379
_reflns_Friedel_fraction_full    0.437

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlis Pro (Agilent Technologies (2011))'
_computing_cell_refinement       'CrysAlis Pro (Agilent Technologies (2011))'
_computing_data_reduction        'CrysAlis Pro (Agilent Technologies (2011))'
_computing_structure_solution    'SIR92 (Altomare et al., 1993)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Mercury (MacRae et al., 2009)'
_computing_publication_material  'SHELXL-2013 (Sheldrick, 2013)'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0453P)²+2.5070P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1374 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.323(7)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         4954
_refine_ls_number_parameters     518
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0253
_refine_ls_R_factor_gt           0.0250
_refine_ls_wR_factor_ref         0.0661
_refine_ls_wR_factor_gt          0.0660
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.045
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Sm1 Sm 0.43942(2) 0.24194(2) 0.09959(3) 0.00910(8) Uani 1 1 d . . . . .
N1A N 0.4721(4) 0.1195(2) 0.0280(2) 0.0132(9) Uani 1 1 d . . . . .
C2A C 0.4106(4) 0.0507(3) 0.0362(3) 0.0133(10) Uani 1 1 d . . . . .
C3A C 0.4390(4) -0.0154(3) -0.0026(3) 0.0184(12) Uani 1 1 d . . . . .
H3A H 0.3972 -0.0636 0.0052 0.022 Uiso 1 1 calc R U . . .
C4A C 0.5285(5) -0.0099(3) -0.0524(3) 0.0211(12) Uani 1 1 d . . . . .
H4A H 0.5484 -0.0543 -0.0794 0.025 Uiso 1 1 calc R U . . .
C5A C 0.5893(5) 0.0606(3) -0.0629(3) 0.0199(12) Uani 1 1 d . . . . .
H5A H 0.6504 0.0655 -0.0973 0.024 Uiso 1 1 calc R U . . .
C6A C 0.5584(4) 0.1236(3) -0.0219(3) 0.0148(12) Uani 1 1 d . . . . .
H6A H 0.5998 0.1721 -0.0290 0.018 Uiso 1 1 calc R U . . .
N7A N 0.3174(4) 0.0504(2) 0.0845(2) 0.0136(10) Uani 1 1 d . . . . .
C7A C 0.2402(5) -0.0176(2) 0.0994(4) 0.0241(11) Uani 1 1 d . . . . .
H7A1 H 0.2580 -0.0363 0.1455 0.036 Uiso 1 1 calc R U . . .
H7A2 H 0.2579 -0.0594 0.0667 0.036 Uiso 1 1 calc R U . . .
H7A3 H 0.1528 -0.0027 0.0962 0.036 Uiso 1 1 calc R U . . .
N8A N 0.3027(4) 0.1164(2) 0.1220(2) 0.0131(9) Uani 1 1 d . . . . .
C9A C 0.2219(4) 0.1178(3) 0.1703(3) 0.0137(10) Uani 1 1 d . . . . .
H9A H 0.1709 0.0739 0.1803 0.016 Uiso 1 1 calc R U . . .
C10A C 0.2139(5) 0.1907(3) 0.2084(3) 0.0127(11) Uani 1 1 d . . . . .
N11A N 0.1479(4) 0.2015(3) 0.2658(2) 0.0156(10) Uani 1 1 d . . . . .
C11A C 0.0746(5) 0.1427(4) 0.3028(3) 0.0260(14) Uani 1 1 d . . . . .
H11A H 0.0335 0.1078 0.2703 0.039 Uiso 1 1 calc R U . . .
H11B H 0.0122 0.1694 0.3307 0.039 Uiso 1 1 calc R U . . .
H11C H 0.1293 0.1119 0.3322 0.039 Uiso 1 1 calc R U . . .
C12A C 0.1699(5) 0.2767(3) 0.2877(3) 0.0233(13) Uani 1 1 d . . . . .
H12A H 0.1367 0.3014 0.3269 0.028 Uiso 1 1 calc R U . . .
C13A C 0.2493(5) 0.3086(3) 0.2415(3) 0.0210(12) Uani 1 1 d . . . . .
H13A H 0.2804 0.3607 0.2434 0.025 Uiso 1 1 calc R U . . .
N14A N 0.2784(5) 0.2549(3) 0.1916(3) 0.0149(12) Uani 1 1 d . . . . .
N1B N 0.5079(4) 0.3615(3) 0.1681(2) 0.0173(10) Uani 1 1 d . . . . .
C2B C 0.4506(5) 0.4324(3) 0.1659(3) 0.0176(12) Uani 1 1 d . . . . .
C3B C 0.4875(6) 0.4935(3) 0.2092(3) 0.0262(13) Uani 1 1 d . . . . .
H3B H 0.4473 0.5430 0.2071 0.031 Uiso 1 1 calc R U . . .
C4B C 0.5821(6) 0.4813(4) 0.2549(3) 0.0312(15) Uani 1 1 d . . . . .
H4B H 0.6062 0.5219 0.2853 0.037 Uiso 1 1 calc R U . . .
C5B C 0.6418(5) 0.4092(4) 0.2561(3) 0.0282(13) Uani 1 1 d . . . . .
H5B H 0.7085 0.3998 0.2864 0.034 Uiso 1 1 calc R U . . .
C6B C 0.6015(5) 0.3519(3) 0.2123(3) 0.0187(11) Uani 1 1 d . . . . .
H6B H 0.6422 0.3025 0.2133 0.022 Uiso 1 1 calc R U . . .
N7B N 0.3520(4) 0.4404(2) 0.1221(2) 0.0177(10) Uani 1 1 d . . . . .
C7B C 0.3028(5) 0.5160(3) 0.1014(4) 0.0276(12) Uani 1 1 d . . . . .
H7B1 H 0.3088 0.5210 0.0519 0.041 Uiso 1 1 calc R U . . .
H7B2 H 0.3505 0.5580 0.1230 0.041 Uiso 1 1 calc R U . . .
H7B3 H 0.2159 0.5199 0.1152 0.041 Uiso 1 1 calc R U . . .
N8B N 0.3178(3) 0.3748(2) 0.0875(2) 0.0132(10) Uani 1 1 d . . . . .
C9B C 0.2263(4) 0.3787(3) 0.0447(3) 0.0145(11) Uani 1 1 d . . . . .
H9B H 0.1799 0.4255 0.0380 0.017 Uiso 1 1 calc R U . . .
C10B C 0.2000(4) 0.3077(3) 0.0081(3) 0.0146(11) Uani 1 1 d . . . . .
N11B N 0.1154(4) 0.3008(3) -0.0428(2) 0.0176(10) Uani 1 1 d . . . . .
C11B C 0.0323(6) 0.3621(4) -0.0688(4) 0.0298(14) Uani 1 1 d . . . . .
H11D H -0.0244 0.3391 -0.1022 0.045 Uiso 1 1 calc R U . . .
H11E H 0.0812 0.4035 -0.0905 0.045 Uiso 1 1 calc R U . . .
H11F H -0.0154 0.3844 -0.0311 0.045 Uiso 1 1 calc R U . . .
C12B C 0.1250(6) 0.2256(4) -0.0670(3) 0.0249(14) Uani 1 1 d . . . . .
H12B H 0.0783 0.2032 -0.1030 0.030 Uiso 1 1 calc R U . . .
C13B C 0.2136(5) 0.1895(4) -0.0299(3) 0.0212(13) Uani 1 1 d . . . . .
H13B H 0.2397 0.1367 -0.0359 0.025 Uiso 1 1 calc R U . . .
N14B N 0.2604(5) 0.2407(2) 0.0180(3) 0.0147(12) Uani 1 1 d . . . . .
S1C S 0.78637(12) 0.24774(6) 0.06638(9) 0.0152(3) Uani 1 1 d . . . . .
O11C O 0.7984(4) 0.3297(2) 0.0543(2) 0.0271(9) Uani 1 1 d . . . . .
O12C O 0.8256(3) 0.1958(2) 0.0130(2) 0.0239(9) Uani 1 1 d . . . . .
O13C O 0.6693(3) 0.22464(19) 0.0981(3) 0.0192(7) Uani 1 1 d . . . . .
C1C C 0.9014(5) 0.2306(4) 0.1337(4) 0.0269(14) Uani 1 1 d . . . . .
F11C F 0.9152(3) 0.1558(2) 0.1482(2) 0.0388(10) Uani 1 1 d . . . . .
F12C F 0.8705(4) 0.2677(3) 0.1911(2) 0.0415(10) Uani 1 1 d . . . . .
F13C F 1.0103(3) 0.2587(2) 0.1141(3) 0.0380(13) Uani 1 1 d . . . . .
S1D S 0.50804(11) 0.10441(7) 0.24609(7) 0.0148(3) Uani 1 1 d . . . . .
O11D O 0.4124(4) 0.1099(3) 0.2966(2) 0.0243(9) Uani 1 1 d . . . . .
O12D O 0.5202(4) 0.0301(2) 0.2124(3) 0.0277(10) Uani 1 1 d . . . . .
O13D O 0.5156(3) 0.1714(2) 0.2001(2) 0.0178(8) Uani 1 1 d . . . . .
C1D C 0.6505(5) 0.1148(4) 0.2951(3) 0.0303(15) Uani 1 1 d . . . . .
F11D F 0.6631(4) 0.0536(3) 0.3368(2) 0.0622(15) Uani 1 1 d . . . . .
F12D F 0.6507(4) 0.1789(3) 0.3310(2) 0.0588(14) Uani 1 1 d . . . . .
F13D F 0.7499(3) 0.1162(2) 0.2555(2) 0.0380(9) Uani 1 1 d . . . . .
S1E S 0.50441(12) 0.38666(7) -0.03727(8) 0.0151(3) Uani 1 1 d . . . . .
O11E O 0.5349(4) 0.4551(2) 0.0018(2) 0.0285(10) Uani 1 1 d . . . . .
O12E O 0.3951(4) 0.3907(2) -0.0790(2) 0.0230(9) Uani 1 1 d . . . . .
O13E O 0.5177(3) 0.3130(2) 0.0005(2) 0.0181(8) Uani 1 1 d . . . . .
C1E C 0.6276(5) 0.3816(4) -0.1004(3) 0.0277(14) Uani 1 1 d . . . . .
F11E F 0.6207(4) 0.3152(3) -0.1360(3) 0.0624(14) Uani 1 1 d . . . . .
F12E F 0.7386(3) 0.3866(3) -0.0752(2) 0.0644(16) Uani 1 1 d . . . . .
F13E F 0.6140(4) 0.4394(3) -0.1453(2) 0.0485(12) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Sm1 O13E 2.447(4) . ?
Sm1 O13D 2.457(4) . ?
Sm1 O13C 2.503(3) . ?
Sm1 N14B 2.515(6) . ?
Sm1 N14A 2.521(6) . ?
Sm1 N1A 2.542(4) . ?
Sm1 N1B 2.553(4) . ?
Sm1 N8B 2.629(4) . ?
Sm1 N8A 2.637(4) . ?
N1A C2A 1.357(6) . ?
N1A C6A 1.357(7) . ?
C2A N7A 1.385(6) . ?
C2A C3A 1.394(7) . ?
C3A C4A 1.381(8) . ?
C3A H3A 0.9500 . ?
C4A C5A 1.383(8) . ?
C4A H4A 0.9500 . ?
C5A C6A 1.384(8) . ?
C5A H5A 0.9500 . ?
C6A H6A 0.9500 . ?
N7A N8A 1.356(5) . ?
N7A C7A 1.457(6) . ?
C7A H7A1 0.9800 . ?
C7A H7A2 0.9800 . ?
C7A H7A3 0.9800 . ?
N8A C9A 1.291(7) . ?
C9A C10A 1.453(7) . ?
C9A H9A 0.9500 . ?
C10A N14A 1.339(7) . ?
C10A N11A 1.347(7) . ?
N11A C12A 1.374(7) . ?
N11A C11A 1.470(7) . ?
C11A H11A 0.9800 . ?
C11A H11B 0.9800 . ?
C11A H11C 0.9800 . ?
C12A C13A 1.363(8) . ?
C12A H12A 0.9500 . ?
C13A N14A 1.380(8) . ?
C13A H13A 0.9500 . ?
N1B C6B 1.344(7) . ?
N1B C2B 1.359(7) . ?
C2B N7B 1.377(7) . ?
C2B C3B 1.403(8) . ?
C3B C4B 1.377(9) . ?
C3B H3B 0.9500 . ?
C4B C5B 1.387(9) . ?
C4B H4B 0.9500 . ?
C5B C6B 1.374(8) . ?
C5B H5B 0.9500 . ?
C6B H6B 0.9500 . ?
N7B N8B 1.360(6) . ?
N7B C7B 1.451(6) . ?
C7B H7B1 0.9800 . ?
C7B H7B2 0.9800 . ?
C7B H7B3 0.9800 . ?
N8B C9B 1.301(6) . ?
C9B C10B 1.437(7) . ?
C9B H9B 0.9500 . ?
C10B N14B 1.329(7) . ?
C10B N11B 1.361(7) . ?
N11B C12B 1.371(8) . ?
N11B C11B 1.470(7) . ?
C11B H11D 0.9800 . ?
C11B H11E 0.9800 . ?
C11B H11F 0.9800 . ?
C12B C13B 1.353(9) . ?
C12B H12B 0.9500 . ?
C13B N14B 1.380(8) . ?
C13B H13B 0.9500 . ?
S1C O11C 1.423(4) . ?
S1C O12C 1.437(4) . ?
S1C O13C 1.465(4) . ?
S1C C1C 1.840(7) . ?
C1C F11C 1.315(7) . ?
C1C F13C 1.328(7) . ?
C1C F12C 1.337(8) . ?
S1D O12D 1.436(4) . ?
S1D O11D 1.437(4) . ?
S1D O13D 1.459(4) . ?
S1D C1D 1.825(6) . ?
C1D F12D 1.301(8) . ?
C1D F13D 1.328(7) . ?
C1D F11D 1.335(7) . ?
S1E O11E 1.435(4) . ?
S1E O12E 1.440(4) . ?
S1E O13E 1.465(4) . ?
S1E C1E 1.824(6) . ?
C1E F12E 1.301(7) . ?
C1E F11E 1.331(8) . ?
C1E F13E 1.332(7) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O13E Sm1 O13D 140.19(11) . . ?
O13E Sm1 O13C 72.89(14) . . ?
O13D Sm1 O13C 67.60(15) . . ?
O13E Sm1 N14B 76.16(15) . . ?
O13D Sm1 N14B 140.18(14) . . ?
O13C Sm1 N14B 139.07(19) . . ?
O13E Sm1 N14A 140.18(14) . . ?
O13D Sm1 N14A 72.29(16) . . ?
O13C Sm1 N14A 134.8(2) . . ?
N14B Sm1 N14A 85.89(17) . . ?
O13E Sm1 N1A 85.20(13) . . ?
O13D Sm1 N1A 89.89(13) . . ?
O13C Sm1 N1A 76.05(14) . . ?
N14B Sm1 N1A 75.29(15) . . ?
N14A Sm1 N1A 124.44(14) . . ?
O13E Sm1 N1B 85.77(14) . . ?
O13D Sm1 N1B 82.39(14) . . ?
O13C Sm1 N1B 79.16(14) . . ?
N14B Sm1 N1B 124.58(15) . . ?
N14A Sm1 N1B 75.60(16) . . ?
N1A Sm1 N1B 155.14(15) . . ?
O13E Sm1 N8B 71.00(12) . . ?
O13D Sm1 N8B 131.45(13) . . ?
O13C Sm1 N8B 126.65(11) . . ?
N14B Sm1 N8B 64.19(13) . . ?
N14A Sm1 N8B 69.19(14) . . ?
N1A Sm1 N8B 136.56(14) . . ?
N1B Sm1 N8B 60.39(14) . . ?
O13E Sm1 N8A 136.77(14) . . ?
O13D Sm1 N8A 69.88(13) . . ?
O13C Sm1 N8A 117.58(11) . . ?
N14B Sm1 N8A 70.68(14) . . ?
N14A Sm1 N8A 64.12(14) . . ?
N1A Sm1 N8A 60.34(13) . . ?
N1B Sm1 N8A 136.15(15) . . ?
N8B Sm1 N8A 115.69(12) . . ?
C2A N1A C6A 117.8(5) . . ?
C2A N1A Sm1 125.1(3) . . ?
C6A N1A Sm1 117.1(3) . . ?
N1A C2A N7A 116.1(4) . . ?
N1A C2A C3A 121.7(5) . . ?
N7A C2A C3A 122.2(4) . . ?
C4A C3A C2A 119.2(5) . . ?
C4A C3A H3A 120.4 . . ?
C2A C3A H3A 120.4 . . ?
C3A C4A C5A 119.8(5) . . ?
C3A C4A H4A 120.1 . . ?
C5A C4A H4A 120.1 . . ?
C4A C5A C6A 118.1(5) . . ?
C4A C5A H5A 120.9 . . ?
C6A C5A H5A 120.9 . . ?
N1A C6A C5A 123.3(5) . . ?
N1A C6A H6A 118.4 . . ?
C5A C6A H6A 118.4 . . ?
N8A N7A C2A 117.2(4) . . ?
N8A N7A C7A 118.8(4) . . ?
C2A N7A C7A 124.0(4) . . ?
N7A C7A H7A1 109.5 . . ?
N7A C7A H7A2 109.5 . . ?
H7A1 C7A H7A2 109.5 . . ?
N7A C7A H7A3 109.5 . . ?
H7A1 C7A H7A3 109.5 . . ?
H7A2 C7A H7A3 109.5 . . ?
C9A N8A N7A 119.8(4) . . ?
C9A N8A Sm1 119.2(3) . . ?
N7A N8A Sm1 121.0(3) . . ?
N8A C9A C10A 115.9(4) . . ?
N8A C9A H9A 122.1 . . ?
C10A C9A H9A 122.1 . . ?
N14A C10A N11A 111.9(5) . . ?
N14A C10A C9A 122.6(5) . . ?
N11A C10A C9A 125.5(5) . . ?
C10A N11A C12A 107.4(4) . . ?
C10A N11A C11A 127.5(5) . . ?
C12A N11A C11A 124.9(5) . . ?
N11A C11A H11A 109.5 . . ?
N11A C11A H11B 109.5 . . ?
H11A C11A H11B 109.5 . . ?
N11A C11A H11C 109.5 . . ?
H11A C11A H11C 109.5 . . ?
H11B C11A H11C 109.5 . . ?
C13A C12A N11A 105.8(5) . . ?
C13A C12A H12A 127.1 . . ?
N11A C12A H12A 127.1 . . ?
C12A C13A N14A 110.7(5) . . ?
C12A C13A H13A 124.6 . . ?
N14A C13A H13A 124.6 . . ?
C10A N14A C13A 104.3(5) . . ?
C10A N14A Sm1 117.8(4) . . ?
C13A N14A Sm1 136.6(4) . . ?
C6B N1B C2B 118.2(5) . . ?
C6B N1B Sm1 117.6(3) . . ?
C2B N1B Sm1 124.1(4) . . ?
N1B C2B N7B 117.5(5) . . ?
N1B C2B C3B 120.6(5) . . ?
N7B C2B C3B 121.8(5) . . ?
C4B C3B C2B 119.8(6) . . ?
C4B C3B H3B 120.1 . . ?
C2B C3B H3B 120.1 . . ?
C3B C4B C5B 119.3(6) . . ?
C3B C4B H4B 120.3 . . ?
C5B C4B H4B 120.3 . . ?
C6B C5B C4B 118.1(6) . . ?
C6B C5B H5B 121.0 . . ?
C4B C5B H5B 121.0 . . ?
N1B C6B C5B 124.0(5) . . ?
N1B C6B H6B 118.0 . . ?
C5B C6B H6B 118.0 . . ?
N8B N7B C2B 116.3(4) . . ?
N8B N7B C7B 119.2(4) . . ?
C2B N7B C7B 123.2(4) . . ?
N7B C7B H7B1 109.5 . . ?
N7B C7B H7B2 109.5 . . ?
H7B1 C7B H7B2 109.5 . . ?
N7B C7B H7B3 109.5 . . ?
H7B1 C7B H7B3 109.5 . . ?
H7B2 C7B H7B3 109.5 . . ?
C9B N8B N7B 119.3(4) . . ?
C9B N8B Sm1 118.9(3) . . ?
N7B N8B Sm1 121.7(3) . . ?
N8B C9B C10B 115.6(4) . . ?
N8B C9B H9B 122.2 . . ?
C10B C9B H9B 122.2 . . ?
N14B C10B N11B 111.3(5) . . ?
N14B C10B C9B 123.6(5) . . ?
N11B C10B C9B 125.0(4) . . ?
C10B N11B C12B 106.6(4) . . ?
C10B N11B C11B 127.3(5) . . ?
C12B N11B C11B 126.0(5) . . ?
N11B C11B H11D 109.5 . . ?
N11B C11B H11E 109.5 . . ?
H11D C11B H11E 109.5 . . ?
N11B C11B H11F 109.5 . . ?
H11D C11B H11F 109.5 . . ?
H11E C11B H11F 109.5 . . ?
C13B C12B N11B 106.9(5) . . ?
C13B C12B H12B 126.6 . . ?
N11B C12B H12B 126.6 . . ?
C12B C13B N14B 109.9(5) . . ?
C12B C13B H13B 125.0 . . ?
N14B C13B H13B 125.0 . . ?
C10B N14B C13B 105.3(5) . . ?
C10B N14B Sm1 117.6(4) . . ?
C13B N14B Sm1 136.4(4) . . ?
O11C S1C O12C 117.1(3) . . ?
O11C S1C O13C 114.4(2) . . ?
O12C S1C O13C 113.7(2) . . ?
O11C S1C C1C 102.3(3) . . ?
O12C S1C C1C 103.2(3) . . ?
O13C S1C C1C 103.5(3) . . ?
S1C O13C Sm1 146.2(3) . . ?
F11C C1C F13C 108.2(5) . . ?
F11C C1C F12C 107.7(6) . . ?
F13C C1C F12C 107.2(6) . . ?
F11C C1C S1C 112.7(5) . . ?
F13C C1C S1C 109.4(5) . . ?
F12C C1C S1C 111.4(4) . . ?
O12D S1D O11D 116.3(3) . . ?
O12D S1D O13D 113.4(3) . . ?
O11D S1D O13D 114.7(2) . . ?
O12D S1D C1D 104.6(3) . . ?
O11D S1D C1D 103.6(3) . . ?
O13D S1D C1D 101.8(2) . . ?
S1D O13D Sm1 149.7(2) . . ?
F12D C1D F13D 107.6(5) . . ?
F12D C1D F11D 108.6(6) . . ?
F13D C1D F11D 107.0(5) . . ?
F12D C1D S1D 111.8(4) . . ?
F13D C1D S1D 112.0(5) . . ?
F11D C1D S1D 109.6(4) . . ?
O11E S1E O12E 117.0(3) . . ?
O11E S1E O13E 113.7(3) . . ?
O12E S1E O13E 114.2(2) . . ?
O11E S1E C1E 103.7(3) . . ?
O12E S1E C1E 102.3(3) . . ?
O13E S1E C1E 103.5(2) . . ?
S1E O13E Sm1 142.6(2) . . ?
F12E C1E F11E 107.9(5) . . ?
F12E C1E F13E 107.9(5) . . ?
F11E C1E F13E 105.9(6) . . ?
F12E C1E S1E 114.2(5) . . ?
F11E C1E S1E 111.0(4) . . ?
F13E C1E S1E 109.7(4) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6A N1A C2A N7A -175.7(4) . . . . ?
Sm1 N1A C2A N7A 4.6(6) . . . . ?
C6A N1A C2A C3A 3.5(7) . . . . ?
Sm1 N1A C2A C3A -176.2(4) . . . . ?
N1A C2A C3A C4A -2.6(8) . . . . ?
N7A C2A C3A C4A 176.5(5) . . . . ?
C2A C3A C4A C5A 0.4(8) . . . . ?
C3A C4A C5A C6A 0.8(8) . . . . ?
C2A N1A C6A C5A -2.2(8) . . . . ?
Sm1 N1A C6A C5A 177.4(4) . . . . ?
C4A C5A C6A N1A 0.2(8) . . . . ?
N1A C2A N7A N8A -4.6(6) . . . . ?
C3A C2A N7A N8A 176.2(4) . . . . ?
N1A C2A N7A C7A 178.9(5) . . . . ?
C3A C2A N7A C7A -0.3(8) . . . . ?
C2A N7A N8A C9A -176.1(4) . . . . ?
C7A N7A N8A C9A 0.5(7) . . . . ?
C2A N7A N8A Sm1 2.8(5) . . . . ?
C7A N7A N8A Sm1 179.4(4) . . . . ?
N7A N8A C9A C10A 179.2(4) . . . . ?
Sm1 N8A C9A C10A 0.2(6) . . . . ?
N8A C9A C10A N14A 5.2(8) . . . . ?
N8A C9A C10A N11A -171.1(5) . . . . ?
N14A C10A N11A C12A 0.1(7) . . . . ?
C9A C10A N11A C12A 176.8(5) . . . . ?
N14A C10A N11A C11A -174.5(6) . . . . ?
C9A C10A N11A C11A 2.2(9) . . . . ?
C10A N11A C12A C13A 0.3(6) . . . . ?
C11A N11A C12A C13A 175.1(6) . . . . ?
N11A C12A C13A N14A -0.6(7) . . . . ?
N11A C10A N14A C13A -0.5(6) . . . . ?
C9A C10A N14A C13A -177.3(5) . . . . ?
N11A C10A N14A Sm1 168.7(4) . . . . ?
C9A C10A N14A Sm1 -8.1(7) . . . . ?
C12A C13A N14A C10A 0.6(7) . . . . ?
C12A C13A N14A Sm1 -165.4(5) . . . . ?
C6B N1B C2B N7B -177.7(5) . . . . ?
Sm1 N1B C2B N7B -2.2(7) . . . . ?
C6B N1B C2B C3B -0.7(8) . . . . ?
Sm1 N1B C2B C3B 174.7(4) . . . . ?
N1B C2B C3B C4B -0.5(9) . . . . ?
N7B C2B C3B C4B 176.3(5) . . . . ?
C2B C3B C4B C5B 1.6(10) . . . . ?
C3B C4B C5B C6B -1.5(10) . . . . ?
C2B N1B C6B C5B 0.9(8) . . . . ?
Sm1 N1B C6B C5B -174.8(4) . . . . ?
C4B C5B C6B N1B 0.2(9) . . . . ?
N1B C2B N7B N8B 3.0(7) . . . . ?
C3B C2B N7B N8B -173.9(5) . . . . ?
N1B C2B N7B C7B -163.6(5) . . . . ?
C3B C2B N7B C7B 19.5(8) . . . . ?
C2B N7B N8B C9B -179.1(5) . . . . ?
C7B N7B N8B C9B -12.0(7) . . . . ?
C2B N7B N8B Sm1 -2.5(6) . . . . ?
C7B N7B N8B Sm1 164.6(4) . . . . ?
N7B N8B C9B C10B 177.4(4) . . . . ?
Sm1 N8B C9B C10B 0.7(6) . . . . ?
N8B C9B C10B N14B 2.3(8) . . . . ?
N8B C9B C10B N11B -174.3(5) . . . . ?
N14B C10B N11B C12B -1.1(6) . . . . ?
C9B C10B N11B C12B 175.9(5) . . . . ?
N14B C10B N11B C11B -179.3(6) . . . . ?
C9B C10B N11B C11B -2.3(9) . . . . ?
C10B N11B C12B C13B 0.5(7) . . . . ?
C11B N11B C12B C13B 178.7(6) . . . . ?
N11B C12B C13B N14B 0.2(8) . . . . ?
N11B C10B N14B C13B 1.2(7) . . . . ?
C9B C10B N14B C13B -175.8(5) . . . . ?
N11B C10B N14B Sm1 172.9(3) . . . . ?
C9B C10B N14B Sm1 -4.2(7) . . . . ?
C12B C13B N14B C10B -0.9(7) . . . . ?
C12B C13B N14B Sm1 -170.1(5) . . . . ?
O11C S1C O13C Sm1 43.6(6) . . . . ?
O12C S1C O13C Sm1 -94.6(5) . . . . ?
C1C S1C O13C Sm1 154.2(5) . . . . ?
O11C S1C C1C F11C -173.5(5) . . . . ?
O12C S1C C1C F11C -51.4(5) . . . . ?
O13C S1C C1C F11C 67.3(5) . . . . ?
O11C S1C C1C F13C -53.0(5) . . . . ?
O12C S1C C1C F13C 69.0(5) . . . . ?
O13C S1C C1C F13C -172.2(4) . . . . ?
O11C S1C C1C F12C 65.4(5) . . . . ?
O12C S1C C1C F12C -172.5(4) . . . . ?
O13C S1C C1C F12C -53.8(5) . . . . ?
O12D S1D O13D Sm1 56.7(5) . . . . ?
O11D S1D O13D Sm1 -80.3(5) . . . . ?
C1D S1D O13D Sm1 168.6(5) . . . . ?
O12D S1D C1D F12D -177.3(4) . . . . ?
O11D S1D C1D F12D -55.0(5) . . . . ?
O13D S1D C1D F12D 64.3(5) . . . . ?
O12D S1D C1D F13D 61.8(5) . . . . ?
O11D S1D C1D F13D -175.9(4) . . . . ?
O13D S1D C1D F13D -56.6(5) . . . . ?
O12D S1D C1D F11D -56.9(5) . . . . ?
O11D S1D C1D F11D 65.4(5) . . . . ?
O13D S1D C1D F11D -175.2(5) . . . . ?
O11E S1E O13E Sm1 61.6(4) . . . . ?
O12E S1E O13E Sm1 -76.3(4) . . . . ?
C1E S1E O13E Sm1 173.3(4) . . . . ?
O11E S1E C1E F12E 50.3(6) . . . . ?
O12E S1E C1E F12E 172.4(5) . . . . ?
O13E S1E C1E F12E -68.6(5) . . . . ?
O11E S1E C1E F11E 172.5(4) . . . . ?
O12E S1E C1E F11E -65.4(5) . . . . ?
O13E S1E C1E F11E 53.6(5) . . . . ?
O11E S1E C1E F13E -70.9(5) . . . . ?
O12E S1E C1E F13E 51.2(5) . . . . ?
O13E S1E C1E F13E 170.2(4) . . . . ?

_refine_diff_density_max         1.019
_refine_diff_density_min         -0.793
_refine_diff_density_rms         0.084

_shelxl_version_number           2013-4

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_02
_database_code_depnum_ccdc_archive 'CCDC 1005949'
_audit_update_record             
;
2016-01-10 deposited with the CCDC.	2024-07-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C25 H26 F9 N10 O9 Pr S3'
_chemical_formula_sum            'C25 H26 F9 N10 O9 Pr S3'
_chemical_formula_weight         1018.65

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Pr Pr -0.2180 2.8214 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x+1/2, y, z+1/2'
'x+1/2, -y, z'

_cell_length_a                   10.9258(3)
_cell_length_b                   17.1974(4)
_cell_length_c                   19.8714(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3733.74(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    6654
_cell_measurement_theta_min      3.7170
_cell_measurement_theta_max      27.9420

_exptl_crystal_description       block
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.812
_exptl_crystal_F_000             2024
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.1
_exptl_absorpt_coefficient_mu    1.580
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.87134
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     0.7107
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_detector_area_resol_mean 16.1544
_diffrn_measurement_method       ω-scan
_diffrn_reflns_number            12868
_diffrn_reflns_av_unetI/netI     0.0342
_diffrn_reflns_av_R_equivalents  0.0251
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         3.014
_diffrn_reflns_theta_max         28.098
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.875
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.875
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.618
_diffrn_reflns_point_group_measured_fraction_full 0.731
_reflns_number_total             5629
_reflns_number_gt                4715
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.371
_reflns_Friedel_fraction_max     0.344
_reflns_Friedel_fraction_full    0.445

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlis Pro (Agilent Technologies (2011))'
_computing_cell_refinement       'CrysAlis Pro (Agilent Technologies (2011))'
_computing_data_reduction        'CrysAlis Pro (Agilent Technologies (2011))'
_computing_structure_solution    'SIR92 (Altomare et al., 1993)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Mercury (MacRae et al., 2009)'
_computing_publication_material  'SHELXL-2013 (Sheldrick, 2013)'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0452P)²+0.6559P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1240 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.430(10)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         5629
_refine_ls_number_parameters     518
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0434
_refine_ls_R_factor_gt           0.0314
_refine_ls_wR_factor_ref         0.0820
_refine_ls_wR_factor_gt          0.0770
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.035
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Pr1 Pr 0.44722(2) 0.24438(2) 0.09994(6) 0.02648(10) Uani 1 1 d . . . . .
N1A N 0.4790(5) 0.1189(3) 0.0301(3) 0.0333(14) Uani 1 1 d . . . . .
C2A C 0.4187(6) 0.0520(4) 0.0380(4) 0.0347(17) Uani 1 1 d . . . . .
C3A C 0.4425(8) -0.0136(4) -0.0020(5) 0.051(2) Uani 1 1 d . . . . .
H3A H 0.4011 -0.0601 0.0052 0.062 Uiso 1 1 calc R U . . .
C4A C 0.5278(8) -0.0074(5) -0.0516(5) 0.056(2) Uani 1 1 d . . . . .
H4A H 0.5440 -0.0497 -0.0794 0.067 Uiso 1 1 calc R U . . .
C5A C 0.5901(8) 0.0609(5) -0.0609(5) 0.052(2) Uani 1 1 d . . . . .
H5A H 0.6493 0.0655 -0.0943 0.062 Uiso 1 1 calc R U . . .
C6A C 0.5631(7) 0.1217(5) -0.0201(5) 0.044(2) Uani 1 1 d . . . . .
H6A H 0.6047 0.1682 -0.0269 0.053 Uiso 1 1 calc R U . . .
N7A N 0.3280(5) 0.0507(3) 0.0872(4) 0.0381(18) Uani 1 1 d . . . . .
C7A C 0.2528(9) -0.0172(4) 0.1044(8) 0.071(3) Uani 1 1 d . . . . .
H7A1 H 0.2766 -0.0365 0.1479 0.107 Uiso 1 1 calc R U . . .
H7A2 H 0.2646 -0.0571 0.0713 0.107 Uiso 1 1 calc R U . . .
H7A3 H 0.1681 -0.0024 0.1055 0.107 Uiso 1 1 calc R U . . .
N8A N 0.3118(5) 0.1174(3) 0.1226(3) 0.0318(15) Uani 1 1 d . . . . .
C9A C 0.2324(7) 0.1190(4) 0.1701(4) 0.0373(19) Uani 1 1 d . . . . .
H9A H 0.1852 0.0756 0.1806 0.045 Uiso 1 1 calc R U . . .
C10A C 0.2196(7) 0.1911(5) 0.2066(5) 0.038(2) Uani 1 1 d . . . . .
N11A N 0.1560(7) 0.1995(4) 0.2640(4) 0.055(2) Uani 1 1 d . . . . .
C11A C 0.0835(9) 0.1418(5) 0.3014(6) 0.078(3) Uani 1 1 d . . . . .
H11A H 0.0216 0.1205 0.2725 0.117 Uiso 1 1 calc R U . . .
H11B H 0.0455 0.1664 0.3394 0.117 Uiso 1 1 calc R U . . .
H11C H 0.1363 0.1008 0.3167 0.117 Uiso 1 1 calc R U . . .
C12A C 0.1734(9) 0.2745(6) 0.2846(6) 0.065(3) Uani 1 1 d . . . . .
H12A H 0.1388 0.2979 0.3223 0.078 Uiso 1 1 calc R U . . .
C13A C 0.2488(9) 0.3078(5) 0.2409(5) 0.062(3) Uani 1 1 d . . . . .
H13A H 0.2763 0.3589 0.2432 0.074 Uiso 1 1 calc R U . . .
N14A N 0.2805(8) 0.2546(3) 0.1911(4) 0.0333(18) Uani 1 1 d . . . . .
N1B N 0.5040(6) 0.3678(3) 0.1682(4) 0.0420(16) Uani 1 1 d . . . . .
C2B C 0.4467(7) 0.4373(4) 0.1640(4) 0.0413(19) Uani 1 1 d . . . . .
C3B C 0.4769(10) 0.5003(5) 0.2032(6) 0.068(3) Uani 1 1 d . . . . .
H3B H 0.4369 0.5476 0.1980 0.082 Uiso 1 1 calc R U . . .
C4B C 0.5671(10) 0.4915(6) 0.2499(6) 0.081(4) Uani 1 1 d . . . . .
H4B H 0.5891 0.5327 0.2777 0.097 Uiso 1 1 calc R U . . .
C5B C 0.6246(10) 0.4218(7) 0.2551(6) 0.080(3) Uani 1 1 d . . . . .
H5B H 0.6865 0.4158 0.2868 0.096 Uiso 1 1 calc R U . . .
C6B C 0.5939(8) 0.3597(5) 0.2147(5) 0.056(2) Uani 1 1 d . . . . .
H6B H 0.6345 0.3125 0.2193 0.067 Uiso 1 1 calc R U . . .
N7B N 0.3524(6) 0.4427(3) 0.1181(3) 0.0447(19) Uani 1 1 d . . . . .
C7B C 0.2960(10) 0.5161(4) 0.0995(8) 0.089(4) Uani 1 1 d . . . . .
H7B1 H 0.3009 0.5228 0.0516 0.134 Uiso 1 1 calc R U . . .
H7B2 H 0.3380 0.5580 0.1214 0.134 Uiso 1 1 calc R U . . .
H7B3 H 0.2117 0.5160 0.1131 0.134 Uiso 1 1 calc R U . . .
N8B N 0.3196(5) 0.3770(3) 0.0842(3) 0.0350(18) Uani 1 1 d . . . . .
C9B C 0.2330(7) 0.3785(4) 0.0401(4) 0.0394(19) Uani 1 1 d . . . . .
H9B H 0.1886 0.4235 0.0313 0.047 Uiso 1 1 calc R U . . .
C10B C 0.2093(7) 0.3076(4) 0.0056(5) 0.042(2) Uani 1 1 d . . . . .
N11B N 0.1254(6) 0.2985(4) -0.0447(5) 0.056(2) Uani 1 1 d . . . . .
C11B C 0.0450(10) 0.3590(6) -0.0726(6) 0.087(4) Uani 1 1 d . . . . .
H11D H -0.0137 0.3356 -0.1022 0.131 Uiso 1 1 calc R U . . .
H11E H 0.0932 0.3960 -0.0971 0.131 Uiso 1 1 calc R U . . .
H11F H 0.0031 0.3849 -0.0365 0.131 Uiso 1 1 calc R U . . .
C12B C 0.1342(10) 0.2235(6) -0.0660(6) 0.071(4) Uani 1 1 d . . . . .
H12B H 0.0899 0.2004 -0.1005 0.086 Uiso 1 1 calc R U . . .
C13B C 0.2207(9) 0.1890(5) -0.0267(5) 0.057(3) Uani 1 1 d . . . . .
H13B H 0.2455 0.1375 -0.0306 0.068 Uiso 1 1 calc R U . . .
N14B N 0.2658(8) 0.2407(4) 0.0192(5) 0.049(3) Uani 1 1 d . . . . .
S1C S 0.79467(18) 0.24993(10) 0.06788(13) 0.0441(5) Uani 1 1 d . . . . .
O11C O 0.8108(7) 0.3281(3) 0.0509(4) 0.093(2) Uani 1 1 d . . . . .
O12C O 0.8320(6) 0.1952(4) 0.0180(4) 0.074(2) Uani 1 1 d . . . . .
O13C O 0.6780(4) 0.2342(3) 0.0975(6) 0.0530(13) Uani 1 1 d . . . . .
C1C C 0.9026(9) 0.2380(6) 0.1359(6) 0.065(3) Uani 1 1 d . . . . .
F11C F 0.9092(7) 0.1651(5) 0.1547(4) 0.123(3) Uani 1 1 d . . . . .
F12C F 0.8731(7) 0.2800(6) 0.1882(4) 0.124(3) Uani 1 1 d . . . . .
F13C F 1.0120(5) 0.2602(4) 0.1175(5) 0.122(4) Uani 1 1 d . . . . .
S1D S 0.5193(2) 0.10916(12) 0.24791(12) 0.0430(5) Uani 1 1 d . . . . .
O11D O 0.4229(5) 0.1130(4) 0.2944(3) 0.0622(17) Uani 1 1 d . . . . .
O12D O 0.5370(7) 0.0352(4) 0.2162(5) 0.090(3) Uani 1 1 d . . . . .
O13D O 0.5246(5) 0.1737(3) 0.2016(3) 0.0506(15) Uani 1 1 d . . . . .
C1D C 0.6540(11) 0.1268(11) 0.2998(7) 0.097(5) Uani 1 1 d . . . . .
F11D F 0.6611(7) 0.0681(8) 0.3439(5) 0.193(6) Uani 1 1 d . . . . .
F12D F 0.6534(9) 0.1868(8) 0.3283(6) 0.187(6) Uani 1 1 d . . . . .
F13D F 0.7553(6) 0.1232(6) 0.2642(4) 0.146(3) Uani 1 1 d . . . . .
S1E S 0.5109(2) 0.38475(12) -0.04198(13) 0.0453(5) Uani 1 1 d . . . . .
O11E O 0.5434(7) 0.4540(4) -0.0066(4) 0.084(2) Uani 1 1 d . . . . .
O12E O 0.4032(6) 0.3874(4) -0.0836(4) 0.070(2) Uani 1 1 d . . . . .
O13E O 0.5212(5) 0.3142(3) -0.0017(3) 0.0503(15) Uani 1 1 d . . . . .
C1E C 0.6341(12) 0.3749(11) -0.1005(9) 0.109(6) Uani 1 1 d . . . . .
F11E F 0.6215(9) 0.3105(8) -0.1367(6) 0.193(6) Uani 1 1 d . . . . .
F12E F 0.7359(7) 0.3760(7) -0.0792(4) 0.193(6) Uani 1 1 d . . . . .
F13E F 0.6244(7) 0.4289(7) -0.1474(5) 0.182(5) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Pr1 O13E 2.484(5) . ?
Pr1 O13D 2.505(6) . ?
Pr1 O13C 2.529(4) . ?
Pr1 N14B 2.550(9) . ?
Pr1 N14A 2.575(8) . ?
Pr1 N1A 2.590(6) . ?
Pr1 N1B 2.594(6) . ?
Pr1 N8A 2.676(5) . ?
Pr1 N8B 2.691(5) . ?
N1A C2A 1.335(8) . ?
N1A C6A 1.357(10) . ?
C2A N7A 1.392(9) . ?
C2A C3A 1.404(10) . ?
C3A C4A 1.361(12) . ?
C3A H3A 0.9300 . ?
C4A C5A 1.370(13) . ?
C4A H4A 0.9300 . ?
C5A C6A 1.355(11) . ?
C5A H5A 0.9300 . ?
C6A H6A 0.9300 . ?
N7A N8A 1.358(7) . ?
N7A C7A 1.468(9) . ?
C7A H7A1 0.9600 . ?
C7A H7A2 0.9600 . ?
C7A H7A3 0.9600 . ?
N8A C9A 1.284(9) . ?
C9A C10A 1.444(11) . ?
C9A H9A 0.9300 . ?
C10A N14A 1.315(10) . ?
C10A N11A 1.342(11) . ?
N11A C12A 1.366(11) . ?
N11A C11A 1.472(11) . ?
C11A H11A 0.9600 . ?
C11A H11B 0.9600 . ?
C11A H11C 0.9600 . ?
C12A C13A 1.327(12) . ?
C12A H12A 0.9300 . ?
C13A N14A 1.392(11) . ?
C13A H13A 0.9300 . ?
N1B C2B 1.351(9) . ?
N1B C6B 1.355(11) . ?
C2B C3B 1.375(12) . ?
C2B N7B 1.379(10) . ?
C3B C4B 1.361(14) . ?
C3B H3B 0.9300 . ?
C4B C5B 1.357(14) . ?
C4B H4B 0.9300 . ?
C5B C6B 1.377(13) . ?
C5B H5B 0.9300 . ?
C6B H6B 0.9300 . ?
N7B N8B 1.364(8) . ?
N7B C7B 1.453(9) . ?
C7B H7B1 0.9600 . ?
C7B H7B2 0.9600 . ?
C7B H7B3 0.9600 . ?
N8B C9B 1.290(9) . ?
C9B C10B 1.423(11) . ?
C9B H9B 0.9300 . ?
C10B N14B 1.334(9) . ?
C10B N11B 1.366(11) . ?
N11B C12B 1.360(13) . ?
N11B C11B 1.470(10) . ?
C11B H11D 0.9600 . ?
C11B H11E 0.9600 . ?
C11B H11F 0.9600 . ?
C12B C13B 1.361(13) . ?
C12B H12B 0.9300 . ?
C13B N14B 1.366(12) . ?
C13B H13B 0.9300 . ?
S1C O11C 1.397(6) . ?
S1C O12C 1.426(7) . ?
S1C O13C 1.430(6) . ?
S1C C1C 1.806(10) . ?
C1C F13C 1.307(11) . ?
C1C F12C 1.307(12) . ?
C1C F11C 1.309(11) . ?
S1D O11D 1.403(6) . ?
S1D O12D 1.432(7) . ?
S1D O13D 1.442(6) . ?
S1D C1D 1.823(13) . ?
C1D F12D 1.176(18) . ?
C1D F13D 1.315(14) . ?
C1D F11D 1.339(15) . ?
S1E O11E 1.429(7) . ?
S1E O12E 1.439(7) . ?
S1E O13E 1.458(5) . ?
S1E C1E 1.787(14) . ?
C1E F12E 1.190(15) . ?
C1E F13E 1.321(13) . ?
C1E F11E 1.33(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O13E Pr1 O13D 141.29(15) . . ?
O13E Pr1 O13C 72.2(3) . . ?
O13D Pr1 O13C 69.2(3) . . ?
O13E Pr1 N14B 75.7(2) . . ?
O13D Pr1 N14B 139.2(2) . . ?
O13C Pr1 N14B 139.6(3) . . ?
O13E Pr1 N14A 140.28(18) . . ?
O13D Pr1 N14A 72.8(2) . . ?
O13C Pr1 N14A 136.4(3) . . ?
N14B Pr1 N14A 84.0(2) . . ?
O13E Pr1 N1A 85.62(19) . . ?
O13D Pr1 N1A 89.0(2) . . ?
O13C Pr1 N1A 78.3(2) . . ?
N14B Pr1 N1A 75.3(2) . . ?
N14A Pr1 N1A 121.90(18) . . ?
O13E Pr1 N1B 87.3(2) . . ?
O13D Pr1 N1B 84.0(2) . . ?
O13C Pr1 N1B 80.1(2) . . ?
N14B Pr1 N1B 122.3(2) . . ?
N14A Pr1 N1B 75.3(2) . . ?
N1A Pr1 N1B 158.47(18) . . ?
O13E Pr1 N8A 135.3(2) . . ?
O13D Pr1 N8A 69.81(17) . . ?
O13C Pr1 N8A 119.87(17) . . ?
N14B Pr1 N8A 69.9(2) . . ?
N14A Pr1 N8A 63.00(18) . . ?
N1A Pr1 N8A 58.93(18) . . ?
N1B Pr1 N8A 135.4(2) . . ?
O13E Pr1 N8B 70.40(17) . . ?
O13D Pr1 N8B 132.8(2) . . ?
O13C Pr1 N8B 124.98(17) . . ?
N14B Pr1 N8B 63.0(2) . . ?
N14A Pr1 N8B 70.00(19) . . ?
N1A Pr1 N8B 135.5(2) . . ?
N1B Pr1 N8B 59.42(19) . . ?
N8A Pr1 N8B 115.13(14) . . ?
C2A N1A C6A 116.8(7) . . ?
C2A N1A Pr1 126.1(5) . . ?
C6A N1A Pr1 117.1(5) . . ?
N1A C2A N7A 116.6(6) . . ?
N1A C2A C3A 122.3(7) . . ?
N7A C2A C3A 121.1(7) . . ?
C4A C3A C2A 118.3(8) . . ?
C4A C3A H3A 120.8 . . ?
C2A C3A H3A 120.8 . . ?
C3A C4A C5A 120.3(8) . . ?
C3A C4A H4A 119.8 . . ?
C5A C4A H4A 119.8 . . ?
C6A C5A C4A 118.2(9) . . ?
C6A C5A H5A 120.9 . . ?
C4A C5A H5A 120.9 . . ?
C5A C6A N1A 124.0(8) . . ?
C5A C6A H6A 118.0 . . ?
N1A C6A H6A 118.0 . . ?
N8A N7A C2A 116.3(5) . . ?
N8A N7A C7A 118.6(7) . . ?
C2A N7A C7A 125.1(6) . . ?
N7A C7A H7A1 109.5 . . ?
N7A C7A H7A2 109.5 . . ?
H7A1 C7A H7A2 109.5 . . ?
N7A C7A H7A3 109.5 . . ?
H7A1 C7A H7A3 109.5 . . ?
H7A2 C7A H7A3 109.5 . . ?
C9A N8A N7A 119.2(6) . . ?
C9A N8A Pr1 118.7(4) . . ?
N7A N8A Pr1 122.1(4) . . ?
N8A C9A C10A 117.0(6) . . ?
N8A C9A H9A 121.5 . . ?
C10A C9A H9A 121.5 . . ?
N14A C10A N11A 111.9(8) . . ?
N14A C10A C9A 123.1(8) . . ?
N11A C10A C9A 124.7(8) . . ?
C10A N11A C12A 106.6(7) . . ?
C10A N11A C11A 129.4(8) . . ?
C12A N11A C11A 124.0(8) . . ?
N11A C11A H11A 109.5 . . ?
N11A C11A H11B 109.5 . . ?
H11A C11A H11B 109.5 . . ?
N11A C11A H11C 109.5 . . ?
H11A C11A H11C 109.5 . . ?
H11B C11A H11C 109.5 . . ?
C13A C12A N11A 107.2(8) . . ?
C13A C12A H12A 126.4 . . ?
N11A C12A H12A 126.4 . . ?
C12A C13A N14A 109.7(8) . . ?
C12A C13A H13A 125.2 . . ?
N14A C13A H13A 125.2 . . ?
C10A N14A C13A 104.6(8) . . ?
C10A N14A Pr1 117.9(5) . . ?
C13A N14A Pr1 136.2(6) . . ?
C2B N1B C6B 117.9(7) . . ?
C2B N1B Pr1 125.5(5) . . ?
C6B N1B Pr1 116.4(5) . . ?
N1B C2B C3B 123.4(8) . . ?
N1B C2B N7B 116.5(6) . . ?
C3B C2B N7B 120.1(8) . . ?
C4B C3B C2B 118.2(9) . . ?
C4B C3B H3B 120.9 . . ?
C2B C3B H3B 120.9 . . ?
C5B C4B C3B 119.0(10) . . ?
C5B C4B H4B 120.5 . . ?
C3B C4B H4B 120.5 . . ?
C4B C5B C6B 121.8(11) . . ?
C4B C5B H5B 119.1 . . ?
C6B C5B H5B 119.1 . . ?
N1B C6B C5B 119.6(9) . . ?
N1B C6B H6B 120.2 . . ?
C5B C6B H6B 120.2 . . ?
N8B N7B C2B 117.8(5) . . ?
N8B N7B C7B 118.8(7) . . ?
C2B N7B C7B 123.0(7) . . ?
N7B C7B H7B1 109.5 . . ?
N7B C7B H7B2 109.5 . . ?
H7B1 C7B H7B2 109.5 . . ?
N7B C7B H7B3 109.5 . . ?
H7B1 C7B H7B3 109.5 . . ?
H7B2 C7B H7B3 109.5 . . ?
C9B N8B N7B 120.8(6) . . ?
C9B N8B Pr1 118.4(4) . . ?
N7B N8B Pr1 120.6(4) . . ?
N8B C9B C10B 116.3(6) . . ?
N8B C9B H9B 121.8 . . ?
C10B C9B H9B 121.8 . . ?
N14B C10B N11B 111.1(7) . . ?
N14B C10B C9B 123.9(8) . . ?
N11B C10B C9B 125.0(7) . . ?
C12B N11B C10B 106.8(6) . . ?
C12B N11B C11B 126.6(8) . . ?
C10B N11B C11B 126.5(8) . . ?
N11B C11B H11D 109.5 . . ?
N11B C11B H11E 109.5 . . ?
H11D C11B H11E 109.5 . . ?
N11B C11B H11F 109.5 . . ?
H11D C11B H11F 109.5 . . ?
H11E C11B H11F 109.5 . . ?
N11B C12B C13B 106.6(8) . . ?
N11B C12B H12B 126.7 . . ?
C13B C12B H12B 126.7 . . ?
C12B C13B N14B 110.4(8) . . ?
C12B C13B H13B 124.8 . . ?
N14B C13B H13B 124.8 . . ?
C10B N14B C13B 105.0(8) . . ?
C10B N14B Pr1 117.8(6) . . ?
C13B N14B Pr1 135.8(6) . . ?
O11C S1C O12C 115.5(5) . . ?
O11C S1C O13C 113.2(4) . . ?
O12C S1C O13C 114.6(4) . . ?
O11C S1C C1C 102.0(5) . . ?
O12C S1C C1C 105.0(5) . . ?
O13C S1C C1C 104.6(6) . . ?
S1C O13C Pr1 152.1(6) . . ?
F13C C1C F12C 106.7(9) . . ?
F13C C1C F11C 108.0(9) . . ?
F12C C1C F11C 108.4(10) . . ?
F13C C1C S1C 110.7(8) . . ?
F12C C1C S1C 111.8(7) . . ?
F11C C1C S1C 111.0(8) . . ?
O11D S1D O12D 115.7(5) . . ?
O11D S1D O13D 114.4(4) . . ?
O12D S1D O13D 113.4(5) . . ?
O11D S1D C1D 103.0(6) . . ?
O12D S1D C1D 106.7(7) . . ?
O13D S1D C1D 101.6(5) . . ?
S1D O13D Pr1 150.9(3) . . ?
F12D C1D F13D 107.7(13) . . ?
F12D C1D F11D 110.3(15) . . ?
F13D C1D F11D 105.5(12) . . ?
F12D C1D S1D 114.4(11) . . ?
F13D C1D S1D 111.6(11) . . ?
F11D C1D S1D 106.9(10) . . ?
O11E S1E O12E 117.4(4) . . ?
O11E S1E O13E 113.9(4) . . ?
O12E S1E O13E 113.9(4) . . ?
O11E S1E C1E 102.2(8) . . ?
O12E S1E C1E 104.2(6) . . ?
O13E S1E C1E 102.7(5) . . ?
S1E O13E Pr1 145.4(3) . . ?
F12E C1E F13E 108.4(12) . . ?
F12E C1E F11E 107.6(14) . . ?
F13E C1E F11E 101.2(16) . . ?
F12E C1E S1E 118.1(14) . . ?
F13E C1E S1E 109.4(10) . . ?
F11E C1E S1E 110.7(10) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6A N1A C2A N7A -176.7(7) . . . . ?
Pr1 N1A C2A N7A 1.9(9) . . . . ?
C6A N1A C2A C3A 1.8(11) . . . . ?
Pr1 N1A C2A C3A -179.6(6) . . . . ?
N1A C2A C3A C4A -1.9(13) . . . . ?
N7A C2A C3A C4A 176.6(8) . . . . ?
C2A C3A C4A C5A 1.3(14) . . . . ?
C3A C4A C5A C6A -0.9(14) . . . . ?
C4A C5A C6A N1A 0.9(14) . . . . ?
C2A N1A C6A C5A -1.3(12) . . . . ?
Pr1 N1A C6A C5A 179.9(7) . . . . ?
N1A C2A N7A N8A -0.9(9) . . . . ?
C3A C2A N7A N8A -179.4(7) . . . . ?
N1A C2A N7A C7A -178.9(8) . . . . ?
C3A C2A N7A C7A 2.5(12) . . . . ?
C2A N7A N8A C9A -177.7(7) . . . . ?
C7A N7A N8A C9A 0.5(11) . . . . ?
C2A N7A N8A Pr1 -0.4(8) . . . . ?
C7A N7A N8A Pr1 177.8(7) . . . . ?
N7A N8A C9A C10A 179.4(7) . . . . ?
Pr1 N8A C9A C10A 2.0(9) . . . . ?
N8A C9A C10A N14A 3.3(13) . . . . ?
N8A C9A C10A N11A -169.0(8) . . . . ?
N14A C10A N11A C12A 2.8(11) . . . . ?
C9A C10A N11A C12A 175.9(8) . . . . ?
N14A C10A N11A C11A -175.1(10) . . . . ?
C9A C10A N11A C11A -2.1(16) . . . . ?
C10A N11A C12A C13A -1.9(12) . . . . ?
C11A N11A C12A C13A 176.2(10) . . . . ?
N11A C12A C13A N14A 0.3(13) . . . . ?
N11A C10A N14A C13A -2.6(11) . . . . ?
C9A C10A N14A C13A -175.7(9) . . . . ?
N11A C10A N14A Pr1 166.2(6) . . . . ?
C9A C10A N14A Pr1 -7.0(12) . . . . ?
C12A C13A N14A C10A 1.3(12) . . . . ?
C12A C13A N14A Pr1 -164.2(7) . . . . ?
C6B N1B C2B C3B 1.6(13) . . . . ?
Pr1 N1B C2B C3B 177.3(7) . . . . ?
C6B N1B C2B N7B -177.5(7) . . . . ?
Pr1 N1B C2B N7B -1.8(10) . . . . ?
N1B C2B C3B C4B -1.8(15) . . . . ?
N7B C2B C3B C4B 177.3(9) . . . . ?
C2B C3B C4B C5B 1.0(17) . . . . ?
C3B C4B C5B C6B -0.2(19) . . . . ?
C2B N1B C6B C5B -0.8(13) . . . . ?
Pr1 N1B C6B C5B -176.8(8) . . . . ?
C4B C5B C6B N1B 0.1(17) . . . . ?
N1B C2B N7B N8B 4.2(10) . . . . ?
C3B C2B N7B N8B -175.0(8) . . . . ?
N1B C2B N7B C7B -169.3(9) . . . . ?
C3B C2B N7B C7B 11.6(14) . . . . ?
C2B N7B N8B C9B -179.3(7) . . . . ?
C7B N7B N8B C9B -5.5(11) . . . . ?
C2B N7B N8B Pr1 -4.7(8) . . . . ?
C7B N7B N8B Pr1 169.1(8) . . . . ?
N7B N8B C9B C10B 177.6(7) . . . . ?
Pr1 N8B C9B C10B 2.9(9) . . . . ?
N8B C9B C10B N14B 3.9(14) . . . . ?
N8B C9B C10B N11B -176.9(8) . . . . ?
N14B C10B N11B C12B -3.2(12) . . . . ?
C9B C10B N11B C12B 177.5(10) . . . . ?
N14B C10B N11B C11B 179.3(10) . . . . ?
C9B C10B N11B C11B 0.0(16) . . . . ?
C10B N11B C12B C13B 1.6(12) . . . . ?
C11B N11B C12B C13B 179.1(11) . . . . ?
N11B C12B C13B N14B 0.5(13) . . . . ?
N11B C10B N14B C13B 3.4(12) . . . . ?
C9B C10B N14B C13B -177.3(9) . . . . ?
N11B C10B N14B Pr1 171.9(6) . . . . ?
C9B C10B N14B Pr1 -8.8(13) . . . . ?
C12B C13B N14B C10B -2.3(13) . . . . ?
C12B C13B N14B Pr1 -167.7(8) . . . . ?
O11C S1C O13C Pr1 48.5(11) . . . . ?
O12C S1C O13C Pr1 -86.9(9) . . . . ?
C1C S1C O13C Pr1 158.7(9) . . . . ?
O11C S1C C1C F13C -54.0(9) . . . . ?
O12C S1C C1C F13C 66.9(8) . . . . ?
O13C S1C C1C F13C -172.2(7) . . . . ?
O11C S1C C1C F12C 64.8(9) . . . . ?
O12C S1C C1C F12C -174.3(8) . . . . ?
O13C S1C C1C F12C -53.4(9) . . . . ?
O11C S1C C1C F11C -173.9(8) . . . . ?
O12C S1C C1C F11C -53.1(9) . . . . ?
O13C S1C C1C F11C 67.9(8) . . . . ?
O11D S1D O13D Pr1 -76.1(9) . . . . ?
O12D S1D O13D Pr1 59.6(9) . . . . ?
C1D S1D O13D Pr1 173.7(9) . . . . ?
O11D S1D C1D F12D -59.1(13) . . . . ?
O12D S1D C1D F12D 178.6(12) . . . . ?
O13D S1D C1D F12D 59.7(13) . . . . ?
O11D S1D C1D F13D 178.3(10) . . . . ?
O12D S1D C1D F13D 56.0(12) . . . . ?
O13D S1D C1D F13D -63.0(12) . . . . ?
O11D S1D C1D F11D 63.4(13) . . . . ?
O12D S1D C1D F11D -58.9(13) . . . . ?
O13D S1D C1D F11D -177.8(12) . . . . ?
O11E S1E O13E Pr1 61.3(7) . . . . ?
O12E S1E O13E Pr1 -77.0(7) . . . . ?
C1E S1E O13E Pr1 171.0(8) . . . . ?
O11E S1E C1E F12E 52.9(15) . . . . ?
O12E S1E C1E F12E 175.6(13) . . . . ?
O13E S1E C1E F12E -65.4(15) . . . . ?
O11E S1E C1E F13E -71.8(15) . . . . ?
O12E S1E C1E F13E 51.0(15) . . . . ?
O13E S1E C1E F13E 170.0(13) . . . . ?
O11E S1E C1E F11E 177.5(11) . . . . ?
O12E S1E C1E F11E -59.8(11) . . . . ?
O13E S1E C1E F11E 59.3(12) . . . . ?

_refine_diff_density_max         0.555
_refine_diff_density_min         -0.490
_refine_diff_density_rms         0.073

_shelxl_version_number           2013-4

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_01
_database_code_depnum_ccdc_archive 'CCDC 1005948'
_audit_update_record             
;
2016-01-10 deposited with the CCDC.	2024-07-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C25 H26 F9 La N10 O9 S3'
_chemical_formula_sum            'C25 H26 F9 La N10 O9 S3'
_chemical_formula_weight         1016.65

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
La La -1.4094 9.0376 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x+1/2, y, z+1/2'
'x+1/2, -y, z'

_cell_length_a                   10.9423(2)
_cell_length_b                   17.2695(4)
_cell_length_c                   19.9168(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3763.64(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    5390
_cell_measurement_theta_min      2.5420
_cell_measurement_theta_max      75.2420

_exptl_crystal_description       block
_exptl_crystal_colour            pink
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.794
_exptl_crystal_F_000             2016
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.07
_exptl_absorpt_coefficient_mu    11.311
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.46505
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_source         'SuperNova (Cu) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Atlas'
_diffrn_measurement_method       ω-scan
_diffrn_detector_area_resol_mean 5.2679

_diffrn_reflns_number            10708
_diffrn_reflns_av_unetI/netI     0.0377
_diffrn_reflns_av_R_equivalents  0.0286
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.558
_diffrn_reflns_theta_max         75.452
_diffrn_reflns_theta_full        70.000
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.785
_diffrn_reflns_point_group_measured_fraction_full 0.813
_reflns_number_total             6116
_reflns_number_gt                5432
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.555
_reflns_Friedel_fraction_max     0.579
_reflns_Friedel_fraction_full    0.616

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlis Pro (Agilent Technologies (2011))'
_computing_cell_refinement       'CrysAlis Pro (Agilent Technologies (2011))'
_computing_data_reduction        'CrysAlis Pro (Agilent Technologies (2011))'
_computing_structure_solution    'SIR92 (Altomare et al., 1993)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Mercury (MacRae et al., 2009)'
_computing_publication_material  'SHELXL-2013 (Sheldrick, 2013)'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0692P)²+5.3146P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1745 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.201(7)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         6116
_refine_ls_number_parameters     518
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0516
_refine_ls_R_factor_gt           0.0457
_refine_ls_wR_factor_ref         0.1280
_refine_ls_wR_factor_gt          0.1218
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.054
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
La1 La 0.45139(3) 0.24723(2) 0.10051(9) 0.03278(15) Uani 1 1 d . . . . .
N1A N 0.4840(8) 0.1183(4) 0.0316(5) 0.0444(18) Uani 1 1 d . . . . .
C2A C 0.4232(10) 0.0525(5) 0.0396(6) 0.049(2) Uani 1 1 d . . . . .
C3A C 0.4482(12) -0.0123(7) -0.0012(8) 0.066(3) Uani 1 1 d . . . . .
H3A H 0.4064 -0.0585 0.0058 0.080 Uiso 1 1 calc R U . . .
C4A C 0.5324(14) -0.0073(9) -0.0501(10) 0.080(4) Uani 1 1 d . . . . .
H4A H 0.5469 -0.0495 -0.0781 0.096 Uiso 1 1 calc R U . . .
C5A C 0.5976(14) 0.0610(9) -0.0589(8) 0.075(4) Uani 1 1 d . . . . .
H5A H 0.6589 0.0651 -0.0911 0.090 Uiso 1 1 calc R U . . .
C6A C 0.5681(12) 0.1219(7) -0.0183(8) 0.060(3) Uani 1 1 d . . . . .
H6A H 0.6081 0.1687 -0.0253 0.072 Uiso 1 1 calc R U . . .
N7A N 0.3327(7) 0.0512(4) 0.0867(5) 0.045(2) Uani 1 1 d . . . . .
C7A C 0.2617(17) -0.0168(6) 0.1076(10) 0.092(5) Uani 1 1 d . . . . .
H7A1 H 0.2876 -0.0330 0.1514 0.138 Uiso 1 1 calc R U . . .
H7A2 H 0.2746 -0.0582 0.0762 0.138 Uiso 1 1 calc R U . . .
H7A3 H 0.1764 -0.0037 0.1087 0.138 Uiso 1 1 calc R U . . .
N8A N 0.3149(7) 0.1177(4) 0.1230(4) 0.0388(17) Uani 1 1 d . . . . .
C9A C 0.2355(9) 0.1198(5) 0.1696(6) 0.047(2) Uani 1 1 d . . . . .
H9A H 0.1883 0.0766 0.1799 0.056 Uiso 1 1 calc R U . . .
C10A C 0.2212(10) 0.1905(7) 0.2058(7) 0.055(3) Uani 1 1 d . . . . .
N11A N 0.1528(11) 0.1997(6) 0.2613(7) 0.074(3) Uani 1 1 d . . . . .
C11A C 0.0806(19) 0.1401(10) 0.2966(12) 0.107(6) Uani 1 1 d . . . . .
H11A H 0.0230 0.1174 0.2660 0.160 Uiso 1 1 calc R U . . .
H11B H 0.0376 0.1634 0.3334 0.160 Uiso 1 1 calc R U . . .
H11C H 0.1344 0.1006 0.3134 0.160 Uiso 1 1 calc R U . . .
C12A C 0.1658(18) 0.2756(8) 0.2822(11) 0.099(6) Uani 1 1 d . . . . .
H12A H 0.1286 0.2991 0.3189 0.119 Uiso 1 1 calc R U . . .
C13A C 0.2422(14) 0.3078(7) 0.2390(9) 0.080(5) Uani 1 1 d . . . . .
H13A H 0.2675 0.3592 0.2401 0.096 Uiso 1 1 calc R U . . .
N14A N 0.2781(10) 0.2548(4) 0.1928(6) 0.048(2) Uani 1 1 d . . . . .
N1B N 0.4968(9) 0.3754(5) 0.1695(6) 0.055(2) Uani 1 1 d . . . . .
C2B C 0.4378(11) 0.4418(5) 0.1630(6) 0.053(3) Uani 1 1 d . . . . .
C3B C 0.4666(15) 0.5054(8) 0.2027(10) 0.080(4) Uani 1 1 d . . . . .
H3B H 0.4259 0.5521 0.1967 0.097 Uiso 1 1 calc R U . . .
C4B C 0.5532(16) 0.4988(10) 0.2496(10) 0.096(6) Uani 1 1 d . . . . .
H4B H 0.5727 0.5410 0.2767 0.115 Uiso 1 1 calc R U . . .
C5B C 0.6123(16) 0.4311(10) 0.2577(10) 0.096(5) Uani 1 1 d . . . . .
H5B H 0.6714 0.4258 0.2909 0.115 Uiso 1 1 calc R U . . .
C6B C 0.5839(13) 0.3695(8) 0.2160(8) 0.069(3) Uani 1 1 d . . . . .
H6B H 0.6265 0.3232 0.2205 0.083 Uiso 1 1 calc R U . . .
N7B N 0.3434(9) 0.4456(5) 0.1154(5) 0.057(2) Uani 1 1 d . . . . .
C7B C 0.2843(19) 0.5166(7) 0.1002(11) 0.102(6) Uani 1 1 d . . . . .
H7B1 H 0.3233 0.5402 0.0621 0.154 Uiso 1 1 calc R U . . .
H7B2 H 0.2898 0.5508 0.1381 0.154 Uiso 1 1 calc R U . . .
H7B3 H 0.1999 0.5070 0.0900 0.154 Uiso 1 1 calc R U . . .
N8B N 0.3180(8) 0.3796(4) 0.0828(5) 0.047(2) Uani 1 1 d . . . . .
C9B C 0.2327(9) 0.3800(6) 0.0369(6) 0.049(2) Uani 1 1 d . . . . .
H9B H 0.1874 0.4242 0.0273 0.059 Uiso 1 1 calc R U . . .
C10B C 0.2127(10) 0.3085(6) 0.0022(7) 0.053(3) Uani 1 1 d . . . . .
N11B N 0.1325(11) 0.2991(7) -0.0505(9) 0.084(4) Uani 1 1 d . . . . .
C11B C 0.052(2) 0.3583(9) -0.0781(14) 0.134(10) Uani 1 1 d . . . . .
H11D H -0.0200 0.3344 -0.0959 0.201 Uiso 1 1 calc R U . . .
H11E H 0.0940 0.3856 -0.1133 0.201 Uiso 1 1 calc R U . . .
H11F H 0.0299 0.3941 -0.0433 0.201 Uiso 1 1 calc R U . . .
C12B C 0.1440(18) 0.2257(9) -0.0701(10) 0.099(7) Uani 1 1 d . . . . .
H12B H 0.1025 0.2024 -0.1055 0.119 Uiso 1 1 calc R U . . .
C13B C 0.2269(14) 0.1907(6) -0.0294(9) 0.076(4) Uani 1 1 d . . . . .
H13B H 0.2517 0.1395 -0.0337 0.091 Uiso 1 1 calc R U . . .
N14B N 0.2700(9) 0.2418(5) 0.0196(7) 0.058(3) Uani 1 1 d . . . . .
S1C S 0.8016(2) 0.25025(13) 0.06852(19) 0.0556(6) Uani 1 1 d . . . . .
O11C O 0.831(2) 0.3293(7) 0.0517(10) 0.159(7) Uani 1 1 d . . . . .
O12C O 0.8437(12) 0.1975(8) 0.0182(8) 0.106(4) Uani 1 1 d . . . . .
O13C O 0.6853(6) 0.2429(6) 0.0997(9) 0.077(2) Uani 1 1 d . . . . .
C1C C 0.9081(12) 0.2390(9) 0.1373(10) 0.082(4) Uani 1 1 d . . . . .
F11C F 0.9025(16) 0.1662(8) 0.1584(8) 0.155(5) Uani 1 1 d . . . . .
F12C F 0.8669(13) 0.2858(12) 0.1876(8) 0.158(6) Uani 1 1 d . . . . .
F13C F 1.0159(8) 0.2578(8) 0.1206(8) 0.143(7) Uani 1 1 d . . . . .
S1D S 0.5216(3) 0.11064(15) 0.24815(14) 0.0508(6) Uani 1 1 d . . . . .
O11D O 0.4224(9) 0.1137(6) 0.2957(6) 0.077(3) Uani 1 1 d . . . . .
O12D O 0.5393(11) 0.0380(6) 0.2146(8) 0.097(4) Uani 1 1 d . . . . .
O13D O 0.5284(7) 0.1753(5) 0.2030(5) 0.061(2) Uani 1 1 d . . . . .
C1D C 0.6554(16) 0.1263(18) 0.3005(11) 0.120(9) Uani 1 1 d . . . . .
F11D F 0.6559(13) 0.0733(15) 0.3494(10) 0.239(13) Uani 1 1 d . . . . .
F12D F 0.6532(19) 0.1865(15) 0.3290(12) 0.232(13) Uani 1 1 d . . . . .
F13D F 0.7559(9) 0.1197(11) 0.2678(8) 0.176(7) Uani 1 1 d . . . . .
S1E S 0.5157(3) 0.38608(16) -0.04511(16) 0.0538(6) Uani 1 1 d . . . . .
O11E O 0.5432(12) 0.4561(6) -0.0104(8) 0.104(5) Uani 1 1 d . . . . .
O12E O 0.4103(10) 0.3878(6) -0.0856(6) 0.079(3) Uani 1 1 d . . . . .
O13E O 0.5262(7) 0.3179(5) -0.0028(5) 0.062(2) Uani 1 1 d . . . . .
C1E C 0.6385(17) 0.3738(15) -0.1026(11) 0.104(7) Uani 1 1 d . . . . .
F11E F 0.6240(15) 0.3115(17) -0.1382(11) 0.220(12) Uani 1 1 d . . . . .
F12E F 0.7414(10) 0.3718(12) -0.0790(8) 0.199(9) Uani 1 1 d . . . . .
F13E F 0.6351(13) 0.4329(13) -0.1454(9) 0.203(10) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
La1 O13E 2.528(9) . ?
La1 O13D 2.534(9) . ?
La1 N14B 2.558(11) . ?
La1 O13C 2.560(6) . ?
La1 N1A 2.639(9) . ?
La1 N14A 2.644(10) . ?
La1 N1B 2.652(10) . ?
La1 N8A 2.727(7) . ?
La1 N8B 2.735(7) . ?
N1A C2A 1.326(13) . ?
N1A C6A 1.356(16) . ?
C2A N7A 1.364(15) . ?
C2A C3A 1.410(15) . ?
C3A C4A 1.34(2) . ?
C3A H3A 0.9300 . ?
C4A C5A 1.39(2) . ?
C4A H4A 0.9300 . ?
C5A C6A 1.365(19) . ?
C5A H5A 0.9300 . ?
C6A H6A 0.9300 . ?
N7A N8A 1.371(11) . ?
N7A C7A 1.468(13) . ?
C7A H7A1 0.9600 . ?
C7A H7A2 0.9600 . ?
C7A H7A3 0.9600 . ?
N8A C9A 1.273(14) . ?
C9A C10A 1.425(15) . ?
C9A H9A 0.9300 . ?
C10A N14A 1.299(14) . ?
C10A N11A 1.345(17) . ?
N11A C12A 1.383(17) . ?
N11A C11A 1.476(18) . ?
C11A H11A 0.9600 . ?
C11A H11B 0.9600 . ?
C11A H11C 0.9600 . ?
C12A C13A 1.32(2) . ?
C12A H12A 0.9300 . ?
C13A N14A 1.356(16) . ?
C13A H13A 0.9300 . ?
N1B C2B 1.322(14) . ?
N1B C6B 1.334(18) . ?
C2B C3B 1.390(17) . ?
C2B N7B 1.403(16) . ?
C3B C4B 1.34(2) . ?
C3B H3B 0.9300 . ?
C4B C5B 1.35(3) . ?
C4B H4B 0.9300 . ?
C5B C6B 1.39(2) . ?
C5B H5B 0.9300 . ?
C6B H6B 0.9300 . ?
N7B N8B 1.341(12) . ?
N7B C7B 1.420(14) . ?
C7B H7B1 0.9600 . ?
C7B H7B2 0.9600 . ?
C7B H7B3 0.9600 . ?
N8B C9B 1.307(14) . ?
C9B C10B 1.432(16) . ?
C9B H9B 0.9300 . ?
C10B N14B 1.356(13) . ?
C10B N11B 1.377(17) . ?
N11B C12B 1.33(2) . ?
N11B C11B 1.456(17) . ?
C11B H11D 0.9600 . ?
C11B H11E 0.9600 . ?
C11B H11F 0.9600 . ?
C12B C13B 1.36(2) . ?
C12B H12B 0.9300 . ?
C13B N14B 1.398(18) . ?
C13B H13B 0.9300 . ?
S1C O13C 1.422(10) . ?
S1C O12C 1.431(13) . ?
S1C O11C 1.443(13) . ?
S1C C1C 1.808(16) . ?
C1C F13C 1.267(18) . ?
C1C F11C 1.327(19) . ?
C1C F12C 1.37(2) . ?
S1D O12D 1.434(11) . ?
S1D O13D 1.435(8) . ?
S1D O11D 1.442(10) . ?
S1D C1D 1.818(17) . ?
C1D F12D 1.19(4) . ?
C1D F13D 1.28(3) . ?
C1D F11D 1.34(2) . ?
S1E O12E 1.407(11) . ?
S1E O11E 1.425(11) . ?
S1E O13E 1.452(8) . ?
S1E C1E 1.78(2) . ?
C1E F12E 1.22(2) . ?
C1E F11E 1.30(3) . ?
C1E F13E 1.33(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O13E La1 O13D 141.7(2) . . ?
O13E La1 N14B 75.9(3) . . ?
O13D La1 N14B 138.4(3) . . ?
O13E La1 O13C 71.7(4) . . ?
O13D La1 O13C 70.0(4) . . ?
N14B La1 O13C 140.4(5) . . ?
O13E La1 N1A 86.6(3) . . ?
O13D La1 N1A 87.7(3) . . ?
N14B La1 N1A 75.3(3) . . ?
O13C La1 N1A 80.6(4) . . ?
O13E La1 N14A 140.7(3) . . ?
O13D La1 N14A 72.7(3) . . ?
N14B La1 N14A 83.3(3) . . ?
O13C La1 N14A 136.3(4) . . ?
N1A La1 N14A 120.0(3) . . ?
O13E La1 N1B 87.6(3) . . ?
O13D La1 N1B 86.0(3) . . ?
N14B La1 N1B 120.1(3) . . ?
O13C La1 N1B 80.8(4) . . ?
N1A La1 N1B 161.4(2) . . ?
N14A La1 N1B 74.5(3) . . ?
O13E La1 N8A 135.0(3) . . ?
O13D La1 N8A 69.4(2) . . ?
N14B La1 N8A 69.4(3) . . ?
O13C La1 N8A 121.6(3) . . ?
N1A La1 N8A 57.8(3) . . ?
N14A La1 N8A 62.2(2) . . ?
N1B La1 N8A 134.6(3) . . ?
O13E La1 N8B 70.4(3) . . ?
O13D La1 N8B 133.8(3) . . ?
N14B La1 N8B 62.3(3) . . ?
O13C La1 N8B 123.8(3) . . ?
N1A La1 N8B 135.2(3) . . ?
N14A La1 N8B 70.5(3) . . ?
N1B La1 N8B 57.9(3) . . ?
N8A La1 N8B 114.51(18) . . ?
C2A N1A C6A 117.8(10) . . ?
C2A N1A La1 126.3(7) . . ?
C6A N1A La1 115.8(7) . . ?
N1A C2A N7A 117.5(9) . . ?
N1A C2A C3A 120.9(11) . . ?
N7A C2A C3A 121.5(10) . . ?
C4A C3A C2A 120.0(12) . . ?
C4A C3A H3A 120.0 . . ?
C2A C3A H3A 120.0 . . ?
C3A C4A C5A 119.8(13) . . ?
C3A C4A H4A 120.1 . . ?
C5A C4A H4A 120.1 . . ?
C6A C5A C4A 117.2(14) . . ?
C6A C5A H5A 121.4 . . ?
C4A C5A H5A 121.4 . . ?
N1A C6A C5A 124.1(13) . . ?
N1A C6A H6A 118.0 . . ?
C5A C6A H6A 118.0 . . ?
C2A N7A N8A 116.8(7) . . ?
C2A N7A C7A 126.3(9) . . ?
N8A N7A C7A 116.5(9) . . ?
N7A C7A H7A1 109.5 . . ?
N7A C7A H7A2 109.5 . . ?
H7A1 C7A H7A2 109.5 . . ?
N7A C7A H7A3 109.5 . . ?
H7A1 C7A H7A3 109.5 . . ?
H7A2 C7A H7A3 109.5 . . ?
C9A N8A N7A 120.4(8) . . ?
C9A N8A La1 118.0(6) . . ?
N7A N8A La1 121.5(6) . . ?
N8A C9A C10A 117.9(9) . . ?
N8A C9A H9A 121.0 . . ?
C10A C9A H9A 121.0 . . ?
N14A C10A N11A 109.2(11) . . ?
N14A C10A C9A 125.4(11) . . ?
N11A C10A C9A 125.3(10) . . ?
C10A N11A C12A 107.6(11) . . ?
C10A N11A C11A 127.4(11) . . ?
C12A N11A C11A 125.0(13) . . ?
N11A C11A H11A 109.5 . . ?
N11A C11A H11B 109.5 . . ?
H11A C11A H11B 109.5 . . ?
N11A C11A H11C 109.5 . . ?
H11A C11A H11C 109.5 . . ?
H11B C11A H11C 109.5 . . ?
C13A C12A N11A 105.5(13) . . ?
C13A C12A H12A 127.2 . . ?
N11A C12A H12A 127.2 . . ?
C12A C13A N14A 109.9(12) . . ?
C12A C13A H13A 125.0 . . ?
N14A C13A H13A 125.0 . . ?
C10A N14A C13A 107.7(11) . . ?
C10A N14A La1 116.1(7) . . ?
C13A N14A La1 135.5(8) . . ?
C2B N1B C6B 118.9(11) . . ?
C2B N1B La1 125.6(8) . . ?
C6B N1B La1 115.5(8) . . ?
N1B C2B C3B 121.3(13) . . ?
N1B C2B N7B 117.8(9) . . ?
C3B C2B N7B 121.0(11) . . ?
C4B C3B C2B 119.5(15) . . ?
C4B C3B H3B 120.3 . . ?
C2B C3B H3B 120.3 . . ?
C3B C4B C5B 119.9(14) . . ?
C3B C4B H4B 120.1 . . ?
C5B C4B H4B 120.1 . . ?
C4B C5B C6B 119.2(16) . . ?
C4B C5B H5B 120.4 . . ?
C6B C5B H5B 120.4 . . ?
N1B C6B C5B 121.2(14) . . ?
N1B C6B H6B 119.4 . . ?
C5B C6B H6B 119.4 . . ?
N8B N7B C2B 116.1(8) . . ?
N8B N7B C7B 122.4(11) . . ?
C2B N7B C7B 121.3(10) . . ?
N7B C7B H7B1 109.5 . . ?
N7B C7B H7B2 109.5 . . ?
H7B1 C7B H7B2 109.5 . . ?
N7B C7B H7B3 109.5 . . ?
H7B1 C7B H7B3 109.5 . . ?
H7B2 C7B H7B3 109.5 . . ?
C9B N8B N7B 118.9(8) . . ?
C9B N8B La1 118.4(6) . . ?
N7B N8B La1 122.5(6) . . ?
N8B C9B C10B 116.3(9) . . ?
N8B C9B H9B 121.8 . . ?
C10B C9B H9B 121.8 . . ?
N14B C10B N11B 113.0(11) . . ?
N14B C10B C9B 122.5(11) . . ?
N11B C10B C9B 124.5(10) . . ?
C12B N11B C10B 105.9(10) . . ?
C12B N11B C11B 128.0(13) . . ?
C10B N11B C11B 126.1(12) . . ?
N11B C11B H11D 109.5 . . ?
N11B C11B H11E 109.5 . . ?
H11D C11B H11E 109.5 . . ?
N11B C11B H11F 109.5 . . ?
H11D C11B H11F 109.5 . . ?
H11E C11B H11F 109.5 . . ?
N11B C12B C13B 108.2(12) . . ?
N11B C12B H12B 125.9 . . ?
C13B C12B H12B 125.9 . . ?
C12B C13B N14B 111.2(11) . . ?
C12B C13B H13B 124.4 . . ?
N14B C13B H13B 124.4 . . ?
C10B N14B C13B 101.5(11) . . ?
C10B N14B La1 119.3(8) . . ?
C13B N14B La1 136.5(8) . . ?
O13C S1C O12C 122.5(8) . . ?
O13C S1C O11C 112.9(10) . . ?
O12C S1C O11C 111.5(10) . . ?
O13C S1C C1C 103.7(9) . . ?
O12C S1C C1C 104.7(8) . . ?
O11C S1C C1C 97.6(9) . . ?
S1C O13C La1 153.5(10) . . ?
F13C C1C F11C 111.6(15) . . ?
F13C C1C F12C 110.4(15) . . ?
F11C C1C F12C 108.2(17) . . ?
F13C C1C S1C 112.0(13) . . ?
F11C C1C S1C 108.2(12) . . ?
F12C C1C S1C 106.2(11) . . ?
O12D S1D O13D 112.4(8) . . ?
O12D S1D O11D 116.1(8) . . ?
O13D S1D O11D 115.0(6) . . ?
O12D S1D C1D 106.8(12) . . ?
O13D S1D C1D 101.6(8) . . ?
O11D S1D C1D 102.9(9) . . ?
S1D O13D La1 150.3(5) . . ?
F12D C1D F13D 110(2) . . ?
F12D C1D F11D 105(3) . . ?
F13D C1D F11D 108(2) . . ?
F12D C1D S1D 112.8(19) . . ?
F13D C1D S1D 112.7(18) . . ?
F11D C1D S1D 108.6(16) . . ?
O12E S1E O11E 115.7(7) . . ?
O12E S1E O13E 114.5(6) . . ?
O11E S1E O13E 112.9(8) . . ?
O12E S1E C1E 104.6(9) . . ?
O11E S1E C1E 104.7(11) . . ?
O13E S1E C1E 102.6(8) . . ?
S1E O13E La1 147.0(5) . . ?
F12E C1E F11E 107(2) . . ?
F12E C1E F13E 107.1(19) . . ?
F11E C1E F13E 106(2) . . ?
F12E C1E S1E 116.9(17) . . ?
F11E C1E S1E 111.0(16) . . ?
F13E C1E S1E 107.5(16) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6A N1A C2A N7A -175.4(10) . . . . ?
La1 N1A C2A N7A 1.8(13) . . . . ?
C6A N1A C2A C3A 2.0(17) . . . . ?
La1 N1A C2A C3A 179.1(9) . . . . ?
N1A C2A C3A C4A -2(2) . . . . ?
N7A C2A C3A C4A 175.5(13) . . . . ?
C2A C3A C4A C5A 2(2) . . . . ?
C3A C4A C5A C6A -3(2) . . . . ?
C2A N1A C6A C5A -3(2) . . . . ?
La1 N1A C6A C5A 179.6(12) . . . . ?
C4A C5A C6A N1A 3(2) . . . . ?
N1A C2A N7A N8A -1.7(13) . . . . ?
C3A C2A N7A N8A -179.0(11) . . . . ?
N1A C2A N7A C7A -174.5(14) . . . . ?
C3A C2A N7A C7A 8.2(19) . . . . ?
C2A N7A N8A C9A -177.1(10) . . . . ?
C7A N7A N8A C9A -3.6(16) . . . . ?
C2A N7A N8A La1 1.0(11) . . . . ?
C7A N7A N8A La1 174.5(11) . . . . ?
N7A N8A C9A C10A 179.9(10) . . . . ?
La1 N8A C9A C10A 1.6(13) . . . . ?
N8A C9A C10A N14A 4(2) . . . . ?
N8A C9A C10A N11A -171.5(13) . . . . ?
N14A C10A N11A C12A 2.2(18) . . . . ?
C9A C10A N11A C12A 178.1(15) . . . . ?
N14A C10A N11A C11A -175.2(17) . . . . ?
C9A C10A N11A C11A 1(3) . . . . ?
C10A N11A C12A C13A -1(2) . . . . ?
C11A N11A C12A C13A 176.6(19) . . . . ?
N11A C12A C13A N14A -1(2) . . . . ?
N11A C10A N14A C13A -2.7(17) . . . . ?
C9A C10A N14A C13A -178.6(14) . . . . ?
N11A C10A N14A La1 168.8(9) . . . . ?
C9A C10A N14A La1 -7.1(18) . . . . ?
C12A C13A N14A C10A 2(2) . . . . ?
C12A C13A N14A La1 -166.9(13) . . . . ?
C6B N1B C2B C3B 1(2) . . . . ?
La1 N1B C2B C3B 178.5(11) . . . . ?
C6B N1B C2B N7B -177.6(12) . . . . ?
La1 N1B C2B N7B -0.5(16) . . . . ?
N1B C2B C3B C4B -2(2) . . . . ?
N7B C2B C3B C4B 177.0(14) . . . . ?
C2B C3B C4B C5B 0(3) . . . . ?
C3B C4B C5B C6B 1(3) . . . . ?
C2B N1B C6B C5B 1(2) . . . . ?
La1 N1B C6B C5B -176.8(13) . . . . ?
C4B C5B C6B N1B -2(3) . . . . ?
N1B C2B N7B N8B 2.9(16) . . . . ?
C3B C2B N7B N8B -176.0(12) . . . . ?
N1B C2B N7B C7B -173.1(15) . . . . ?
C3B C2B N7B C7B 8(2) . . . . ?
C2B N7B N8B C9B -178.6(10) . . . . ?
C7B N7B N8B C9B -2.6(19) . . . . ?
C2B N7B N8B La1 -4.1(13) . . . . ?
C7B N7B N8B La1 171.9(13) . . . . ?
N7B N8B C9B C10B 178.0(10) . . . . ?
La1 N8B C9B C10B 3.2(13) . . . . ?
N8B C9B C10B N14B 6.1(19) . . . . ?
N8B C9B C10B N11B -175.7(13) . . . . ?
N14B C10B N11B C12B -4(2) . . . . ?
C9B C10B N11B C12B 177.8(15) . . . . ?
N14B C10B N11B C11B 176(2) . . . . ?
C9B C10B N11B C11B -2(3) . . . . ?
C10B N11B C12B C13B 1(2) . . . . ?
C11B N11B C12B C13B -179(2) . . . . ?
N11B C12B C13B N14B 1(2) . . . . ?
N11B C10B N14B C13B 4.4(17) . . . . ?
C9B C10B N14B C13B -177.2(13) . . . . ?
N11B C10B N14B La1 168.8(10) . . . . ?
C9B C10B N14B La1 -12.8(18) . . . . ?
C12B C13B N14B C10B -3(2) . . . . ?
C12B C13B N14B La1 -163.5(14) . . . . ?
O12C S1C O13C La1 -68.9(18) . . . . ?
O11C S1C O13C La1 68.8(19) . . . . ?
C1C S1C O13C La1 173.3(16) . . . . ?
O13C S1C C1C F13C -168.1(13) . . . . ?
O12C S1C C1C F13C 62.4(15) . . . . ?
O11C S1C C1C F13C -52.3(16) . . . . ?
O13C S1C C1C F11C 68.5(15) . . . . ?
O12C S1C C1C F11C -61.0(16) . . . . ?
O11C S1C C1C F11C -175.7(17) . . . . ?
O13C S1C C1C F12C -47.5(13) . . . . ?
O12C S1C C1C F12C -177.0(13) . . . . ?
O11C S1C C1C F12C 68.3(15) . . . . ?
O12D S1D O13D La1 59.5(14) . . . . ?
O11D S1D O13D La1 -76.3(14) . . . . ?
C1D S1D O13D La1 173.3(15) . . . . ?
O12D S1D C1D F12D 177(2) . . . . ?
O13D S1D C1D F12D 59(2) . . . . ?
O11D S1D C1D F12D -60(2) . . . . ?
O12D S1D C1D F13D 52(2) . . . . ?
O13D S1D C1D F13D -66(2) . . . . ?
O11D S1D C1D F13D 175.0(19) . . . . ?
O12D S1D C1D F11D -67(2) . . . . ?
O13D S1D C1D F11D 175(2) . . . . ?
O11D S1D C1D F11D 56(3) . . . . ?
O12E S1E O13E La1 -74.0(12) . . . . ?
O11E S1E O13E La1 61.1(13) . . . . ?
C1E S1E O13E La1 173.3(12) . . . . ?
O12E S1E C1E F12E 179(2) . . . . ?
O11E S1E C1E F12E 57(2) . . . . ?
O13E S1E C1E F12E -61(2) . . . . ?
O12E S1E C1E F11E -57.4(19) . . . . ?
O11E S1E C1E F11E -179.6(18) . . . . ?
O13E S1E C1E F11E 62.4(18) . . . . ?
O12E S1E C1E F13E 59(2) . . . . ?
O11E S1E C1E F13E -64(2) . . . . ?
O13E S1E C1E F13E 178.3(17) . . . . ?

_refine_diff_density_max         1.054
_refine_diff_density_min         -0.766
_refine_diff_density_rms         0.096

_shelxl_version_number           2013-4

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_05
_database_code_depnum_ccdc_archive 'CCDC 1005951'
_audit_update_record             
;
2016-01-10 deposited with the CCDC.	2024-07-03 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C25 H26 Eu F9 N10 O9 S3'
_chemical_formula_sum            'C25 H26 Eu F9 N10 O9 S3'
_chemical_formula_weight         1029.70

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Eu Eu -0.1578 3.6682 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x+1/2, y, z+1/2'
'x+1/2, -y, z'

_cell_length_a                   10.8953(2)
_cell_length_b                   17.1060(3)
_cell_length_c                   19.8121(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3692.48(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    5766
_cell_measurement_theta_min      3.2090
_cell_measurement_theta_max      27.9360

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.852
_exptl_crystal_F_000             2040
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.1
_exptl_absorpt_coefficient_mu    1.977
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.64927
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     0.7107
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_detector_area_resol_mean 16.1544
_diffrn_measurement_method       ω-scan
_diffrn_reflns_number            51185
_diffrn_reflns_av_unetI/netI     0.0140
_diffrn_reflns_av_R_equivalents  0.0202
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         3.024
_diffrn_reflns_theta_max         28.226
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.955
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.955
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.915
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             8358
_reflns_number_gt                7868
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.863
_reflns_Friedel_fraction_max     0.874
_reflns_Friedel_fraction_full    0.999

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlis Pro (Agilent Technologies (2011))'
_computing_cell_refinement       'CrysAlis Pro (Agilent Technologies (2011))'
_computing_data_reduction        'CrysAlis Pro (Agilent Technologies (2011))'
_computing_structure_solution    'SIR92 (Altomare et al., 1993)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Mercury (MacRae et al., 2009)'
_computing_publication_material  'SHELXL-2013 (Sheldrick, 2013)'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0364P)²+3.6370P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 3531 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.265(2)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         8358
_refine_ls_number_parameters     518
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0286
_refine_ls_R_factor_gt           0.0257
_refine_ls_wR_factor_ref         0.0680
_refine_ls_wR_factor_gt          0.0659
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.037
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Eu1 Eu 0.44331(2) 0.24269(2) 0.10012(3) 0.02693(7) Uani 1 1 d . . . . .
N1A N 0.4789(4) 0.1206(2) 0.0290(2) 0.0342(9) Uani 1 1 d . . . . .
C2A C 0.4192(5) 0.0526(3) 0.0367(3) 0.0352(11) Uani 1 1 d . . . . .
C3A C 0.4433(6) -0.0132(3) -0.0037(3) 0.0485(14) Uani 1 1 d . . . . .
H3A H 0.4012 -0.0599 0.0028 0.058 Uiso 1 1 calc R U . . .
C4A C 0.5307(7) -0.0062(4) -0.0527(3) 0.0550(16) Uani 1 1 d . . . . .
H4A H 0.5503 -0.0491 -0.0796 0.066 Uiso 1 1 calc R U . . .
C5A C 0.5891(6) 0.0628(4) -0.0624(3) 0.0512(15) Uani 1 1 d . . . . .
H5A H 0.6469 0.0680 -0.0966 0.061 Uiso 1 1 calc R U . . .
C6A C 0.5619(5) 0.1249(4) -0.0212(3) 0.0434(13) Uani 1 1 d . . . . .
H6A H 0.6026 0.1720 -0.0283 0.052 Uiso 1 1 calc R U . . .
N7A N 0.3280(4) 0.0507(2) 0.0858(2) 0.0373(11) Uani 1 1 d . . . . .
C7A C 0.2517(7) -0.0171(3) 0.1000(5) 0.0682(19) Uani 1 1 d . . . . .
H7A1 H 0.2737 -0.0385 0.1431 0.102 Uiso 1 1 calc R U . . .
H7A2 H 0.2642 -0.0559 0.0656 0.102 Uiso 1 1 calc R U . . .
H7A3 H 0.1670 -0.0017 0.1006 0.102 Uiso 1 1 calc R U . . .
N8A N 0.3114(4) 0.1171(2) 0.1219(2) 0.0319(9) Uani 1 1 d . . . . .
C9A C 0.2303(5) 0.1188(3) 0.1697(3) 0.0351(11) Uani 1 1 d . . . . .
H9A H 0.1809 0.0759 0.1796 0.042 Uiso 1 1 calc R U . . .
C10A C 0.2212(5) 0.1906(4) 0.2061(3) 0.0377(13) Uani 1 1 d . . . . .
N11A N 0.1545(5) 0.2009(3) 0.2633(3) 0.0473(13) Uani 1 1 d . . . . .
C11A C 0.0833(8) 0.1424(5) 0.3003(4) 0.069(2) Uani 1 1 d . . . . .
H11A H 0.0225 0.1202 0.2709 0.104 Uiso 1 1 calc R U . . .
H11B H 0.0436 0.1668 0.3381 0.104 Uiso 1 1 calc R U . . .
H11C H 0.1371 0.1020 0.3161 0.104 Uiso 1 1 calc R U . . .
C12A C 0.1752(7) 0.2757(4) 0.2840(4) 0.0591(18) Uani 1 1 d . . . . .
H12A H 0.1422 0.2996 0.3220 0.071 Uiso 1 1 calc R U . . .
C13A C 0.2520(7) 0.3086(3) 0.2392(4) 0.0543(16) Uani 1 1 d . . . . .
H13A H 0.2811 0.3597 0.2411 0.065 Uiso 1 1 calc R U . . .
N14A N 0.2814(6) 0.2544(3) 0.1895(3) 0.0362(13) Uani 1 1 d . . . . .
N1B N 0.5076(5) 0.3618(3) 0.1673(2) 0.0422(10) Uani 1 1 d . . . . .
C2B C 0.4519(5) 0.4330(3) 0.1640(3) 0.0409(12) Uani 1 1 d . . . . .
C3B C 0.4870(8) 0.4943(4) 0.2055(4) 0.071(2) Uani 1 1 d . . . . .
H3B H 0.4486 0.5426 0.2017 0.085 Uiso 1 1 calc R U . . .
C4B C 0.5771(8) 0.4836(5) 0.2514(5) 0.081(3) Uani 1 1 d . . . . .
H4B H 0.6000 0.5242 0.2801 0.097 Uiso 1 1 calc R U . . .
C5B C 0.6340(7) 0.4133(5) 0.2553(4) 0.072(2) Uani 1 1 d . . . . .
H5B H 0.6972 0.4056 0.2861 0.087 Uiso 1 1 calc R U . . .
C6B C 0.5980(6) 0.3534(4) 0.2136(3) 0.0508(14) Uani 1 1 d . . . . .
H6B H 0.6371 0.3052 0.2174 0.061 Uiso 1 1 calc R U . . .
N7B N 0.3573(5) 0.4403(2) 0.1189(2) 0.0456(12) Uani 1 1 d . . . . .
C7B C 0.3084(8) 0.5154(3) 0.0982(6) 0.077(2) Uani 1 1 d . . . . .
H7B1 H 0.3187 0.5215 0.0504 0.115 Uiso 1 1 calc R U . . .
H7B2 H 0.3515 0.5564 0.1213 0.115 Uiso 1 1 calc R U . . .
H7B3 H 0.2227 0.5179 0.1093 0.115 Uiso 1 1 calc R U . . .
N8B N 0.3226(4) 0.3744(2) 0.0854(2) 0.0358(11) Uani 1 1 d . . . . .
C9B C 0.2330(5) 0.3776(3) 0.0432(3) 0.0399(12) Uani 1 1 d . . . . .
H9B H 0.1887 0.4232 0.0358 0.048 Uiso 1 1 calc R U . . .
C10B C 0.2056(5) 0.3058(3) 0.0081(3) 0.0392(12) Uani 1 1 d . . . . .
N11B N 0.1219(5) 0.2974(3) -0.0417(3) 0.0524(13) Uani 1 1 d . . . . .
C11B C 0.0404(8) 0.3584(5) -0.0691(5) 0.079(3) Uani 1 1 d . . . . .
H11D H -0.0113 0.3361 -0.1033 0.119 Uiso 1 1 calc R U . . .
H11E H 0.0889 0.3995 -0.0884 0.119 Uiso 1 1 calc R U . . .
H11F H -0.0096 0.3792 -0.0335 0.119 Uiso 1 1 calc R U . . .
C12B C 0.1305(8) 0.2231(5) -0.0634(4) 0.062(2) Uani 1 1 d . . . . .
H12B H 0.0851 0.2003 -0.0979 0.075 Uiso 1 1 calc R U . . .
C13B C 0.2173(7) 0.1882(4) -0.0258(4) 0.0546(18) Uani 1 1 d . . . . .
H13B H 0.2413 0.1362 -0.0301 0.065 Uiso 1 1 calc R U . . .
N14B N 0.2650(6) 0.2397(3) 0.0193(4) 0.0425(14) Uani 1 1 d . . . . .
S1C S 0.78783(13) 0.24995(7) 0.06763(9) 0.0406(3) Uani 1 1 d . . . . .
O11C O 0.7998(5) 0.3296(3) 0.0524(3) 0.0771(15) Uani 1 1 d . . . . .
O12C O 0.8285(5) 0.1962(3) 0.0172(3) 0.0645(13) Uani 1 1 d . . . . .
O13C O 0.6722(3) 0.2293(2) 0.0987(4) 0.0464(8) Uani 1 1 d . . . . .
C1C C 0.8996(7) 0.2369(5) 0.1350(5) 0.067(2) Uani 1 1 d . . . . .
F11C F 0.9117(5) 0.1628(4) 0.1520(4) 0.112(2) Uani 1 1 d . . . . .
F12C F 0.8703(6) 0.2771(5) 0.1900(3) 0.120(2) Uani 1 1 d . . . . .
F13C F 1.0083(4) 0.2621(4) 0.1151(4) 0.110(3) Uani 1 1 d . . . . .
S1D S 0.51480(13) 0.10730(9) 0.24562(8) 0.0411(3) Uani 1 1 d . . . . .
O11D O 0.4190(4) 0.1122(3) 0.2934(2) 0.0625(13) Uani 1 1 d . . . . .
O12D O 0.5306(6) 0.0333(3) 0.2135(3) 0.0761(16) Uani 1 1 d . . . . .
O13D O 0.5200(4) 0.1728(3) 0.1989(2) 0.0480(10) Uani 1 1 d . . . . .
C1D C 0.6522(7) 0.1211(7) 0.2955(5) 0.082(3) Uani 1 1 d . . . . .
F11D F 0.6599(6) 0.0647(6) 0.3404(4) 0.162(4) Uani 1 1 d . . . . .
F12D F 0.6510(7) 0.1848(6) 0.3268(4) 0.155(3) Uani 1 1 d . . . . .
F13D F 0.7516(5) 0.1201(5) 0.2594(3) 0.134(3) Uani 1 1 d . . . . .
S1E S 0.50858(14) 0.38327(9) -0.03926(9) 0.0452(3) Uani 1 1 d . . . . .
O11E O 0.5436(6) 0.4530(3) -0.0033(3) 0.0837(18) Uani 1 1 d . . . . .
O12E O 0.4006(4) 0.3859(3) -0.0810(3) 0.0672(14) Uani 1 1 d . . . . .
O13E O 0.5190(4) 0.3117(2) 0.0003(2) 0.0460(9) Uani 1 1 d . . . . .
C1E C 0.6292(8) 0.3736(7) -0.1009(5) 0.085(3) Uani 1 1 d . . . . .
F11E F 0.6183(9) 0.3062(7) -0.1331(5) 0.178(4) Uani 1 1 d . . . . .
F12E F 0.7353(5) 0.3779(6) -0.0792(3) 0.177(4) Uani 1 1 d . . . . .
F13E F 0.6169(6) 0.4261(6) -0.1478(4) 0.173(4) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Eu1 O13D 2.440(4) . ?
Eu1 O13E 2.445(4) . ?
Eu1 O13C 2.504(3) . ?
Eu1 N14A 2.508(6) . ?
Eu1 N14B 2.518(6) . ?
Eu1 N1B 2.532(5) . ?
Eu1 N1A 2.549(4) . ?
Eu1 N8A 2.621(4) . ?
Eu1 N8B 2.626(4) . ?
N1A C2A 1.342(7) . ?
N1A C6A 1.346(7) . ?
C2A N7A 1.391(7) . ?
C2A C3A 1.406(7) . ?
C3A C4A 1.365(9) . ?
C3A H3A 0.9300 . ?
C4A C5A 1.355(10) . ?
C4A H4A 0.9300 . ?
C5A C6A 1.372(9) . ?
C5A H5A 0.9300 . ?
C6A H6A 0.9300 . ?
N7A N8A 1.354(5) . ?
N7A C7A 1.453(7) . ?
C7A H7A1 0.9600 . ?
C7A H7A2 0.9600 . ?
C7A H7A3 0.9600 . ?
N8A C9A 1.295(7) . ?
C9A C10A 1.428(8) . ?
C9A H9A 0.9300 . ?
C10A N14A 1.315(8) . ?
C10A N11A 1.358(8) . ?
N11A C12A 1.363(9) . ?
N11A C11A 1.462(8) . ?
C11A H11A 0.9600 . ?
C11A H11B 0.9600 . ?
C11A H11C 0.9600 . ?
C12A C13A 1.344(9) . ?
C12A H12A 0.9300 . ?
C13A N14A 1.389(8) . ?
C13A H13A 0.9300 . ?
N1B C6B 1.354(8) . ?
N1B C2B 1.362(7) . ?
C2B N7B 1.371(8) . ?
C2B C3B 1.385(8) . ?
C3B C4B 1.351(12) . ?
C3B H3B 0.9300 . ?
C4B C5B 1.356(12) . ?
C4B H4B 0.9300 . ?
C5B C6B 1.373(10) . ?
C5B H5B 0.9300 . ?
C6B H6B 0.9300 . ?
N7B N8B 1.362(6) . ?
N7B C7B 1.448(7) . ?
C7B H7B1 0.9600 . ?
C7B H7B2 0.9600 . ?
C7B H7B3 0.9600 . ?
N8B C9B 1.287(7) . ?
C9B C10B 1.442(8) . ?
C9B H9B 0.9300 . ?
C10B N14B 1.322(7) . ?
C10B N11B 1.350(8) . ?
N11B C12B 1.346(10) . ?
N11B C11B 1.473(8) . ?
C11B H11D 0.9600 . ?
C11B H11E 0.9600 . ?
C11B H11F 0.9600 . ?
C12B C13B 1.344(10) . ?
C12B H12B 0.9300 . ?
C13B N14B 1.359(9) . ?
C13B H13B 0.9300 . ?
S1C O11C 1.402(4) . ?
S1C O12C 1.428(5) . ?
S1C O13C 1.446(5) . ?
S1C C1C 1.821(8) . ?
C1C F11C 1.317(10) . ?
C1C F13C 1.321(9) . ?
C1C F12C 1.327(11) . ?
S1D O11D 1.411(5) . ?
S1D O12D 1.427(6) . ?
S1D O13D 1.455(4) . ?
S1D C1D 1.809(8) . ?
C1D F12D 1.254(13) . ?
C1D F13D 1.298(10) . ?
C1D F11D 1.315(10) . ?
S1E O12E 1.439(5) . ?
S1E O11E 1.441(6) . ?
S1E O13E 1.459(4) . ?
S1E C1E 1.801(9) . ?
C1E F12E 1.236(11) . ?
C1E F13E 1.301(10) . ?
C1E F11E 1.323(14) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O13D Eu1 O13E 140.28(13) . . ?
O13D Eu1 O13C 67.89(19) . . ?
O13E Eu1 O13C 72.49(19) . . ?
O13D Eu1 N14A 73.38(18) . . ?
O13E Eu1 N14A 140.30(15) . . ?
O13C Eu1 N14A 135.7(2) . . ?
O13D Eu1 N14B 139.83(16) . . ?
O13E Eu1 N14B 75.86(18) . . ?
O13C Eu1 N14B 139.4(2) . . ?
N14A Eu1 N14B 84.71(18) . . ?
O13D Eu1 N1B 83.01(15) . . ?
O13E Eu1 N1B 86.74(15) . . ?
O13C Eu1 N1B 78.70(17) . . ?
N14A Eu1 N1B 76.07(17) . . ?
N14B Eu1 N1B 124.31(17) . . ?
O13D Eu1 N1A 89.42(15) . . ?
O13E Eu1 N1A 84.09(14) . . ?
O13C Eu1 N1A 76.54(16) . . ?
N14A Eu1 N1A 124.27(14) . . ?
N14B Eu1 N1A 75.49(17) . . ?
N1B Eu1 N1A 155.17(15) . . ?
O13D Eu1 N8A 69.75(13) . . ?
O13E Eu1 N8A 135.54(14) . . ?
O13C Eu1 N8A 118.23(13) . . ?
N14A Eu1 N8A 64.12(14) . . ?
N14B Eu1 N8A 70.45(15) . . ?
N1B Eu1 N8A 136.45(15) . . ?
N1A Eu1 N8A 60.20(13) . . ?
O13D Eu1 N8B 132.90(15) . . ?
O13E Eu1 N8B 70.44(13) . . ?
O13C Eu1 N8B 125.18(13) . . ?
N14A Eu1 N8B 69.94(15) . . ?
N14B Eu1 N8B 63.91(15) . . ?
N1B Eu1 N8B 60.41(15) . . ?
N1A Eu1 N8B 135.90(14) . . ?
N8A Eu1 N8B 116.56(12) . . ?
C2A N1A C6A 117.3(5) . . ?
C2A N1A Eu1 125.0(3) . . ?
C6A N1A Eu1 117.7(4) . . ?
N1A C2A N7A 116.5(4) . . ?
N1A C2A C3A 122.5(5) . . ?
N7A C2A C3A 120.9(5) . . ?
C4A C3A C2A 117.8(6) . . ?
C4A C3A H3A 121.1 . . ?
C2A C3A H3A 121.1 . . ?
C5A C4A C3A 120.3(6) . . ?
C5A C4A H4A 119.9 . . ?
C3A C4A H4A 119.9 . . ?
C4A C5A C6A 119.3(6) . . ?
C4A C5A H5A 120.3 . . ?
C6A C5A H5A 120.3 . . ?
N1A C6A C5A 122.8(6) . . ?
N1A C6A H6A 118.6 . . ?
C5A C6A H6A 118.6 . . ?
N8A N7A C2A 116.4(4) . . ?
N8A N7A C7A 119.4(5) . . ?
C2A N7A C7A 124.2(5) . . ?
N7A C7A H7A1 109.5 . . ?
N7A C7A H7A2 109.5 . . ?
H7A1 C7A H7A2 109.5 . . ?
N7A C7A H7A3 109.5 . . ?
H7A1 C7A H7A3 109.5 . . ?
H7A2 C7A H7A3 109.5 . . ?
C9A N8A N7A 119.7(4) . . ?
C9A N8A Eu1 118.4(3) . . ?
N7A N8A Eu1 121.8(3) . . ?
N8A C9A C10A 115.8(5) . . ?
N8A C9A H9A 122.1 . . ?
C10A C9A H9A 122.1 . . ?
N14A C10A N11A 111.6(6) . . ?
N14A C10A C9A 123.6(5) . . ?
N11A C10A C9A 124.7(5) . . ?
C10A N11A C12A 106.5(5) . . ?
C10A N11A C11A 127.9(6) . . ?
C12A N11A C11A 125.4(5) . . ?
N11A C11A H11A 109.5 . . ?
N11A C11A H11B 109.5 . . ?
H11A C11A H11B 109.5 . . ?
N11A C11A H11C 109.5 . . ?
H11A C11A H11C 109.5 . . ?
H11B C11A H11C 109.5 . . ?
C13A C12A N11A 107.3(5) . . ?
C13A C12A H12A 126.3 . . ?
N11A C12A H12A 126.3 . . ?
C12A C13A N14A 109.4(6) . . ?
C12A C13A H13A 125.3 . . ?
N14A C13A H13A 125.3 . . ?
C10A N14A C13A 105.2(6) . . ?
C10A N14A Eu1 117.4(4) . . ?
C13A N14A Eu1 135.7(4) . . ?
C6B N1B C2B 116.8(5) . . ?
C6B N1B Eu1 118.1(4) . . ?
C2B N1B Eu1 124.9(4) . . ?
N1B C2B N7B 116.6(5) . . ?
N1B C2B C3B 121.7(6) . . ?
N7B C2B C3B 121.7(6) . . ?
C4B C3B C2B 119.9(8) . . ?
C4B C3B H3B 120.1 . . ?
C2B C3B H3B 120.1 . . ?
C3B C4B C5B 119.3(7) . . ?
C3B C4B H4B 120.3 . . ?
C5B C4B H4B 120.3 . . ?
C4B C5B C6B 119.8(7) . . ?
C4B C5B H5B 120.1 . . ?
C6B C5B H5B 120.1 . . ?
N1B C6B C5B 122.4(7) . . ?
N1B C6B H6B 118.8 . . ?
C5B C6B H6B 118.8 . . ?
N8B N7B C2B 116.8(4) . . ?
N8B N7B C7B 119.6(6) . . ?
C2B N7B C7B 122.8(5) . . ?
N7B C7B H7B1 109.5 . . ?
N7B C7B H7B2 109.5 . . ?
H7B1 C7B H7B2 109.5 . . ?
N7B C7B H7B3 109.5 . . ?
H7B1 C7B H7B3 109.5 . . ?
H7B2 C7B H7B3 109.5 . . ?
C9B N8B N7B 119.5(4) . . ?
C9B N8B Eu1 119.2(3) . . ?
N7B N8B Eu1 121.2(3) . . ?
N8B C9B C10B 115.8(5) . . ?
N8B C9B H9B 122.1 . . ?
C10B C9B H9B 122.1 . . ?
N14B C10B N11B 111.3(5) . . ?
N14B C10B C9B 123.0(5) . . ?
N11B C10B C9B 125.7(5) . . ?
C12B N11B C10B 106.7(5) . . ?
C12B N11B C11B 126.3(6) . . ?
C10B N11B C11B 126.9(6) . . ?
N11B C11B H11D 109.5 . . ?
N11B C11B H11E 109.5 . . ?
H11D C11B H11E 109.5 . . ?
N11B C11B H11F 109.5 . . ?
H11D C11B H11F 109.5 . . ?
H11E C11B H11F 109.5 . . ?
C13B C12B N11B 106.9(6) . . ?
C13B C12B H12B 126.5 . . ?
N11B C12B H12B 126.5 . . ?
C12B C13B N14B 110.2(6) . . ?
C12B C13B H13B 124.9 . . ?
N14B C13B H13B 124.9 . . ?
C10B N14B C13B 104.9(6) . . ?
C10B N14B Eu1 117.9(4) . . ?
C13B N14B Eu1 136.6(5) . . ?
O11C S1C O12C 116.6(4) . . ?
O11C S1C O13C 114.2(3) . . ?
O12C S1C O13C 114.2(3) . . ?
O11C S1C C1C 102.4(4) . . ?
O12C S1C C1C 103.1(4) . . ?
O13C S1C C1C 103.9(4) . . ?
S1C O13C Eu1 148.2(4) . . ?
F11C C1C F13C 107.5(7) . . ?
F11C C1C F12C 108.2(8) . . ?
F13C C1C F12C 107.0(8) . . ?
F11C C1C S1C 111.8(6) . . ?
F13C C1C S1C 109.8(6) . . ?
F12C C1C S1C 112.2(6) . . ?
O11D S1D O12D 116.2(4) . . ?
O11D S1D O13D 114.2(3) . . ?
O12D S1D O13D 113.3(3) . . ?
O11D S1D C1D 103.8(4) . . ?
O12D S1D C1D 105.0(5) . . ?
O13D S1D C1D 102.4(3) . . ?
S1D O13D Eu1 151.0(3) . . ?
F12D C1D F13D 106.9(9) . . ?
F12D C1D F11D 107.7(9) . . ?
F13D C1D F11D 108.1(9) . . ?
F12D C1D S1D 112.1(7) . . ?
F13D C1D S1D 112.9(7) . . ?
F11D C1D S1D 109.1(7) . . ?
O12E S1E O11E 118.4(4) . . ?
O12E S1E O13E 113.5(3) . . ?
O11E S1E O13E 114.1(3) . . ?
O12E S1E C1E 102.1(4) . . ?
O11E S1E C1E 102.6(5) . . ?
O13E S1E C1E 103.3(4) . . ?
S1E O13E Eu1 144.5(3) . . ?
F12E C1E F13E 107.7(9) . . ?
F12E C1E F11E 107.7(10) . . ?
F13E C1E F11E 104.4(10) . . ?
F12E C1E S1E 116.2(8) . . ?
F13E C1E S1E 110.2(7) . . ?
F11E C1E S1E 110.0(7) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6A N1A C2A N7A -175.8(5) . . . . ?
Eu1 N1A C2A N7A 2.7(6) . . . . ?
C6A N1A C2A C3A 2.1(8) . . . . ?
Eu1 N1A C2A C3A -179.5(4) . . . . ?
N1A C2A C3A C4A -0.4(9) . . . . ?
N7A C2A C3A C4A 177.4(5) . . . . ?
C2A C3A C4A C5A -1.6(10) . . . . ?
C3A C4A C5A C6A 1.8(10) . . . . ?
C2A N1A C6A C5A -1.8(8) . . . . ?
Eu1 N1A C6A C5A 179.6(5) . . . . ?
C4A C5A C6A N1A -0.1(10) . . . . ?
N1A C2A N7A N8A -1.8(7) . . . . ?
C3A C2A N7A N8A -179.7(5) . . . . ?
N1A C2A N7A C7A 178.3(6) . . . . ?
C3A C2A N7A C7A 0.3(9) . . . . ?
C2A N7A N8A C9A -178.2(5) . . . . ?
C7A N7A N8A C9A 1.8(8) . . . . ?
C2A N7A N8A Eu1 0.3(6) . . . . ?
C7A N7A N8A Eu1 -179.8(5) . . . . ?
N7A N8A C9A C10A 178.5(5) . . . . ?
Eu1 N8A C9A C10A 0.0(6) . . . . ?
N8A C9A C10A N14A 6.4(9) . . . . ?
N8A C9A C10A N11A -170.7(6) . . . . ?
N14A C10A N11A C12A -0.5(8) . . . . ?
C9A C10A N11A C12A 176.8(6) . . . . ?
N14A C10A N11A C11A -175.1(7) . . . . ?
C9A C10A N11A C11A 2.3(11) . . . . ?
C10A N11A C12A C13A 0.5(8) . . . . ?
C11A N11A C12A C13A 175.2(8) . . . . ?
N11A C12A C13A N14A -0.3(9) . . . . ?
N11A C10A N14A C13A 0.4(8) . . . . ?
C9A C10A N14A C13A -177.0(6) . . . . ?
N11A C10A N14A Eu1 167.9(4) . . . . ?
C9A C10A N14A Eu1 -9.5(8) . . . . ?
C12A C13A N14A C10A -0.1(8) . . . . ?
C12A C13A N14A Eu1 -164.1(6) . . . . ?
C6B N1B C2B N7B -177.5(5) . . . . ?
Eu1 N1B C2B N7B -2.6(7) . . . . ?
C6B N1B C2B C3B 0.8(9) . . . . ?
Eu1 N1B C2B C3B 175.7(5) . . . . ?
N1B C2B C3B C4B -1.2(12) . . . . ?
N7B C2B C3B C4B 177.0(7) . . . . ?
C2B C3B C4B C5B 1.4(14) . . . . ?
C3B C4B C5B C6B -1.2(15) . . . . ?
C2B N1B C6B C5B -0.7(10) . . . . ?
Eu1 N1B C6B C5B -175.9(6) . . . . ?
C4B C5B C6B N1B 0.9(13) . . . . ?
N1B C2B N7B N8B 4.6(7) . . . . ?
C3B C2B N7B N8B -173.7(6) . . . . ?
N1B C2B N7B C7B -165.2(7) . . . . ?
C3B C2B N7B C7B 16.5(10) . . . . ?
C2B N7B N8B C9B 179.0(5) . . . . ?
C7B N7B N8B C9B -10.9(8) . . . . ?
C2B N7B N8B Eu1 -4.6(6) . . . . ?
C7B N7B N8B Eu1 165.5(6) . . . . ?
N7B N8B C9B C10B 177.7(5) . . . . ?
Eu1 N8B C9B C10B 1.2(6) . . . . ?
N8B C9B C10B N14B 2.0(9) . . . . ?
N8B C9B C10B N11B -174.9(5) . . . . ?
N14B C10B N11B C12B -1.1(8) . . . . ?
C9B C10B N11B C12B 176.2(6) . . . . ?
N14B C10B N11B C11B -178.7(7) . . . . ?
C9B C10B N11B C11B -1.4(11) . . . . ?
C10B N11B C12B C13B 1.0(9) . . . . ?
C11B N11B C12B C13B 178.6(8) . . . . ?
N11B C12B C13B N14B -0.6(10) . . . . ?
N11B C10B N14B C13B 0.7(8) . . . . ?
C9B C10B N14B C13B -176.6(6) . . . . ?
N11B C10B N14B Eu1 173.0(4) . . . . ?
C9B C10B N14B Eu1 -4.3(8) . . . . ?
C12B C13B N14B C10B 0.0(9) . . . . ?
C12B C13B N14B Eu1 -170.2(6) . . . . ?
O11C S1C O13C Eu1 44.5(8) . . . . ?
O12C S1C O13C Eu1 -93.2(6) . . . . ?
C1C S1C O13C Eu1 155.2(6) . . . . ?
O11C S1C C1C F11C -173.5(6) . . . . ?
O12C S1C C1C F11C -52.1(7) . . . . ?
O13C S1C C1C F11C 67.4(7) . . . . ?
O11C S1C C1C F13C -54.1(7) . . . . ?
O12C S1C C1C F13C 67.2(7) . . . . ?
O13C S1C C1C F13C -173.3(6) . . . . ?
O11C S1C C1C F12C 64.8(7) . . . . ?
O12C S1C C1C F12C -173.9(6) . . . . ?
O13C S1C C1C F12C -54.4(7) . . . . ?
O11D S1D O13D Eu1 -76.6(7) . . . . ?
O12D S1D O13D Eu1 59.4(7) . . . . ?
C1D S1D O13D Eu1 172.0(6) . . . . ?
O11D S1D C1D F12D -57.8(8) . . . . ?
O12D S1D C1D F12D 179.8(7) . . . . ?
O13D S1D C1D F12D 61.3(8) . . . . ?
O11D S1D C1D F13D -178.6(8) . . . . ?
O12D S1D C1D F13D 59.0(9) . . . . ?
O13D S1D C1D F13D -59.5(9) . . . . ?
O11D S1D C1D F11D 61.3(9) . . . . ?
O12D S1D C1D F11D -61.1(9) . . . . ?
O13D S1D C1D F11D -179.6(8) . . . . ?
O12E S1E O13E Eu1 -76.9(5) . . . . ?
O11E S1E O13E Eu1 62.7(6) . . . . ?
C1E S1E O13E Eu1 173.3(5) . . . . ?
O12E S1E C1E F12E 172.8(9) . . . . ?
O11E S1E C1E F12E 49.7(10) . . . . ?
O13E S1E C1E F12E -69.2(10) . . . . ?
O12E S1E C1E F13E 50.0(10) . . . . ?
O11E S1E C1E F13E -73.1(10) . . . . ?
O13E S1E C1E F13E 168.0(9) . . . . ?
O12E S1E C1E F11E -64.6(8) . . . . ?
O11E S1E C1E F11E 172.4(8) . . . . ?
O13E S1E C1E F11E 53.5(8) . . . . ?

_refine_diff_density_max         1.043
_refine_diff_density_min         -0.508
_refine_diff_density_rms         0.066

_shelxl_version_number           2013-4

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_21
_audit_block_doi                 10.5517/ccdc.csd.cc1k5v6s
_database_code_depnum_ccdc_archive 'CCDC 1435585'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/C7QI00727B 2018
_audit_update_record             
;
2015-11-06 deposited with the CCDC.	2024-07-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C11 H15 Er N8 O10'
_chemical_formula_sum            'C11 H15 Er N8 O10'
_chemical_formula_weight         586.57

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Er Er -0.2586 4.9576 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.3705(7)
_cell_length_b                   9.3039(7)
_cell_length_c                   12.7182(9)
_cell_angle_alpha                102.222(6)
_cell_angle_beta                 103.692(7)
_cell_angle_gamma                102.763(6)
_cell_volume                     901.39(13)
_cell_formula_units_Z            2
_cell_measurement_temperature    120(1)
_cell_measurement_reflns_used    2892
_cell_measurement_theta_min      3.2620
_cell_measurement_theta_max      27.0350

_exptl_crystal_description       prism
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.161
_exptl_crystal_F_000             570
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_exptl_absorpt_coefficient_mu    4.730
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.49757
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      120(1)
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Eos
_diffrn_detector_area_resol_mean 16.1544
_diffrn_measurement_method       ω-scan
_diffrn_reflns_number            3145
_diffrn_reflns_av_unetI/netI     0.0456
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.263
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             3145
_reflns_number_gt                2826
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlis Pro (Agilent Technologies (2011))'
_computing_cell_refinement       'CrysAlis Pro (Agilent Technologies (2011))'
_computing_data_reduction        'CrysAlis Pro (Agilent Technologies (2011))'
_computing_structure_solution    'SIR92 (Altomare et al., 1993)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Mercury (MacRae et al., 2009)'
_computing_publication_material  'SHELXL-2013 (Sheldrick, 2013)'

_refine_special_details          
;
 Refined as a 2-component twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0900P)²+2.8494P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3145
_refine_ls_number_parameters     274
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0648
_refine_ls_R_factor_gt           0.0572
_refine_ls_wR_factor_ref         0.1539
_refine_ls_wR_factor_gt          0.1485
_refine_ls_goodness_of_fit_ref   1.234
_refine_ls_restrained_S_all      1.234
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Er1 Er 0.64794(5) 0.26890(5) 0.69741(4) 0.0226(2) Uani 1 1 d . . . . .
N1A N 0.4752(10) 0.3752(10) 0.8063(7) 0.0214(17) Uani 1 1 d . . . . .
C2A C 0.3345(13) 0.2787(14) 0.8157(8) 0.030(2) Uani 1 1 d . . . . .
H2A H 0.3137 0.1715 0.7853 0.036 Uiso 1 1 calc R U . . .
C3A C 0.2227(13) 0.3265(13) 0.8657(9) 0.030(2) Uani 1 1 d . . . . .
H3A H 0.1273 0.2549 0.8717 0.036 Uiso 1 1 calc R U . . .
C4A C 0.2513(14) 0.4839(13) 0.9084(9) 0.031(2) Uani 1 1 d . . . . .
H4A H 0.1737 0.5212 0.9426 0.037 Uiso 1 1 calc R U . . .
C5A C 0.3921(13) 0.5847(13) 0.9007(9) 0.028(2) Uani 1 1 d . . . . .
H5A H 0.4128 0.6922 0.9291 0.033 Uiso 1 1 calc R U . . .
C6A C 0.5027(13) 0.5275(11) 0.8511(8) 0.022(2) Uani 1 1 d . . . . .
N7A N 0.6503(10) 0.6247(10) 0.8428(7) 0.0236(18) Uani 1 1 d . . . . .
C71A C 0.7082(14) 0.7896(12) 0.8915(9) 0.030(2) Uani 1 1 d . . . . .
H71C H 0.6899 0.8403 0.8314 0.046 Uiso 1 1 calc R U . . .
H71B H 0.8306 0.8211 0.9331 0.046 Uiso 1 1 calc R U . . .
H71A H 0.6431 0.8190 0.9431 0.046 Uiso 1 1 calc R U . . .
N8A N 0.7432(11) 0.5539(10) 0.7826(7) 0.0237(18) Uani 1 1 d . . . . .
C9A C 0.8782(12) 0.6348(11) 0.7707(9) 0.024(2) Uani 1 1 d . . . . .
H9A H 0.9189 0.7430 0.8016 0.028 Uiso 1 1 calc R U . . .
C10A C 0.9639(12) 0.5499(12) 0.7073(8) 0.023(2) Uani 1 1 d . . . . .
N11A N 1.1077(11) 0.6084(11) 0.6797(8) 0.028(2) Uani 1 1 d . . . . .
C11A C 1.2039(15) 0.7705(13) 0.7113(11) 0.037(3) Uani 1 1 d . . . . .
H11C H 1.3164 0.7796 0.6988 0.055 Uiso 1 1 calc R U . . .
H11B H 1.2194 0.8170 0.7911 0.055 Uiso 1 1 calc R U . . .
H11A H 1.1405 0.8236 0.6652 0.055 Uiso 1 1 calc R U . . .
C12A C 1.1436(13) 0.4883(13) 0.6208(9) 0.028(2) Uani 1 1 d . . . . .
H12A H 1.2380 0.4933 0.5910 0.033 Uiso 1 1 calc R U . . .
C13A C 1.0227(14) 0.3590(13) 0.6112(9) 0.028(2) Uani 1 1 d . . . . .
H13A H 1.0162 0.2580 0.5719 0.034 Uiso 1 1 calc R U . . .
N14A N 0.9097(11) 0.3983(10) 0.6680(8) 0.0275(19) Uani 1 1 d . . . . .
N1B N 0.7617(11) 0.1911(10) 0.9010(7) 0.0269(19) Uani 1 1 d . . . . .
O11B O 0.6168(9) 0.1125(8) 0.8289(6) 0.0300(16) Uani 1 1 d . . . . .
O12B O 0.8440(9) 0.3064(8) 0.8771(6) 0.0250(15) Uani 1 1 d . . . . .
O13B O 0.8129(11) 0.1588(10) 0.9879(7) 0.0384(19) Uani 1 1 d . . . . .
N1C N 0.4920(11) 0.2957(10) 0.4777(7) 0.0243(18) Uani 1 1 d . . . . .
O11C O 0.4684(10) 0.3660(9) 0.5669(6) 0.0306(17) Uani 1 1 d . . . . .
O12C O 0.5995(9) 0.2162(8) 0.4947(6) 0.0249(15) Uani 1 1 d . . . . .
O13C O 0.4198(11) 0.2975(9) 0.3849(7) 0.0362(18) Uani 1 1 d . . . . .
N1D N 0.8562(11) -0.0071(10) 0.6534(8) 0.030(2) Uani 1 1 d . . . . .
O11D O 0.7485(10) 0.0669(9) 0.6322(6) 0.0348(18) Uani 1 1 d . . . . .
O12D O 0.8803(11) -0.0887(10) 0.5721(7) 0.0374(19) Uani 1 1 d . . . . .
O13D O 0.9280(10) 0.0001(9) 0.7522(6) 0.0356(18) Uani 1 1 d . . . . .
O1E O 0.3889(9) 0.0699(8) 0.6150(6) 0.0259(15) Uani 1 1 d . . . . .
H1E1 H 0.3979 -0.0157 0.5815 0.031 Uiso 1 1 d R U . . .
H1E2 H 0.3186 0.0872 0.5649 0.031 Uiso 1 1 d R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Er1 O11D 2.302(7) . ?
Er1 O1E 2.357(7) . ?
Er1 O12B 2.381(7) . ?
Er1 N14A 2.409(9) . ?
Er1 O11C 2.426(7) . ?
Er1 O12C 2.436(7) . ?
Er1 N1A 2.446(8) . ?
Er1 O11B 2.460(7) . ?
Er1 N8A 2.506(9) . ?
Er1 N1B 2.840(8) . ?
Er1 N1C 2.878(8) . ?
N1A C6A 1.356(13) . ?
N1A C2A 1.361(14) . ?
C2A C3A 1.351(15) . ?
C2A H2A 0.9500 . ?
C3A C4A 1.394(16) . ?
C3A H3A 0.9500 . ?
C4A C5A 1.372(15) . ?
C4A H4A 0.9500 . ?
C5A C6A 1.374(15) . ?
C5A H5A 0.9500 . ?
C6A N7A 1.402(13) . ?
N7A N8A 1.385(12) . ?
N7A C71A 1.449(14) . ?
C71A H71C 0.9800 . ?
C71A H71B 0.9800 . ?
C71A H71A 0.9800 . ?
N8A C9A 1.273(13) . ?
C9A C10A 1.430(15) . ?
C9A H9A 0.9500 . ?
C10A N14A 1.325(13) . ?
C10A N11A 1.363(13) . ?
N11A C12A 1.342(14) . ?
N11A C11A 1.463(14) . ?
C11A H11C 0.9800 . ?
C11A H11B 0.9800 . ?
C11A H11A 0.9800 . ?
C12A C13A 1.352(16) . ?
C12A H12A 0.9500 . ?
C13A N14A 1.384(14) . ?
C13A H13A 0.9500 . ?
N1B O13B 1.211(11) . ?
N1B O12B 1.276(11) . ?
N1B O11B 1.282(12) . ?
N1C O13C 1.197(11) . ?
N1C O11C 1.265(12) . ?
N1C O12C 1.294(11) . ?
N1D O12D 1.232(12) . ?
N1D O13D 1.239(12) . ?
N1D O11D 1.264(12) . ?
O1E H1E1 0.8482 . ?
O1E H1E2 0.8282 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O11D Er1 O1E 79.3(3) . . ?
O11D Er1 O12B 87.0(3) . . ?
O1E Er1 O12B 124.8(2) . . ?
O11D Er1 N14A 78.1(3) . . ?
O1E Er1 N14A 144.9(3) . . ?
O12B Er1 N14A 80.3(3) . . ?
O11D Er1 O11C 120.6(3) . . ?
O1E Er1 O11C 75.1(3) . . ?
O12B Er1 O11C 150.2(3) . . ?
N14A Er1 O11C 93.9(3) . . ?
O11D Er1 O12C 69.5(2) . . ?
O1E Er1 O12C 74.4(2) . . ?
O12B Er1 O12C 147.1(2) . . ?
N14A Er1 O12C 72.7(3) . . ?
O11C Er1 O12C 52.4(2) . . ?
O11D Er1 N1A 149.3(3) . . ?
O1E Er1 N1A 81.5(3) . . ?
O12B Er1 N1A 84.6(2) . . ?
N14A Er1 N1A 129.0(3) . . ?
O11C Er1 N1A 76.4(3) . . ?
O12C Er1 N1A 127.2(2) . . ?
O11D Er1 O11B 76.6(3) . . ?
O1E Er1 O11B 71.6(2) . . ?
O12B Er1 O11B 53.2(2) . . ?
N14A Er1 O11B 127.5(3) . . ?
O11C Er1 O11B 138.5(2) . . ?
O12C Er1 O11B 135.5(2) . . ?
N1A Er1 O11B 74.8(3) . . ?
O11D Er1 N8A 141.8(3) . . ?
O1E Er1 N8A 138.3(3) . . ?
O12B Er1 N8A 75.7(3) . . ?
N14A Er1 N8A 65.7(3) . . ?
O11C Er1 N8A 75.3(3) . . ?
O12C Er1 N8A 108.6(2) . . ?
N1A Er1 N8A 63.4(3) . . ?
O11B Er1 N8A 116.0(3) . . ?
O11D Er1 N1B 80.1(3) . . ?
O1E Er1 N1B 98.4(2) . . ?
O12B Er1 N1B 26.5(2) . . ?
N14A Er1 N1B 103.8(3) . . ?
O11C Er1 N1B 155.5(3) . . ?
O12C Er1 N1B 149.6(2) . . ?
N1A Er1 N1B 79.2(3) . . ?
O11B Er1 N1B 26.8(3) . . ?
N8A Er1 N1B 96.5(3) . . ?
O11D Er1 N1C 95.2(3) . . ?
O1E Er1 N1C 72.1(2) . . ?
O12B Er1 N1C 162.9(2) . . ?
N14A Er1 N1C 83.6(3) . . ?
O11C Er1 N1C 25.8(2) . . ?
O12C Er1 N1C 26.5(2) . . ?
N1A Er1 N1C 101.3(3) . . ?
O11B Er1 N1C 143.7(2) . . ?
N8A Er1 N1C 92.5(3) . . ?
N1B Er1 N1C 170.1(2) . . ?
C6A N1A C2A 116.9(9) . . ?
C6A N1A Er1 123.8(6) . . ?
C2A N1A Er1 119.0(7) . . ?
C3A C2A N1A 123.8(11) . . ?
C3A C2A H2A 118.1 . . ?
N1A C2A H2A 118.1 . . ?
C2A C3A C4A 118.1(10) . . ?
C2A C3A H3A 120.9 . . ?
C4A C3A H3A 120.9 . . ?
C5A C4A C3A 119.7(10) . . ?
C5A C4A H4A 120.1 . . ?
C3A C4A H4A 120.1 . . ?
C4A C5A C6A 118.9(11) . . ?
C4A C5A H5A 120.5 . . ?
C6A C5A H5A 120.5 . . ?
N1A C6A C5A 122.5(9) . . ?
N1A C6A N7A 116.0(9) . . ?
C5A C6A N7A 121.5(9) . . ?
N8A N7A C6A 115.8(8) . . ?
N8A N7A C71A 119.7(8) . . ?
C6A N7A C71A 124.5(8) . . ?
N7A C71A H71C 109.5 . . ?
N7A C71A H71B 109.5 . . ?
H71C C71A H71B 109.5 . . ?
N7A C71A H71A 109.5 . . ?
H71C C71A H71A 109.5 . . ?
H71B C71A H71A 109.5 . . ?
C9A N8A N7A 119.5(9) . . ?
C9A N8A Er1 119.9(7) . . ?
N7A N8A Er1 120.7(6) . . ?
N8A C9A C10A 114.7(9) . . ?
N8A C9A H9A 122.6 . . ?
C10A C9A H9A 122.6 . . ?
N14A C10A N11A 111.1(9) . . ?
N14A C10A C9A 122.2(9) . . ?
N11A C10A C9A 126.7(10) . . ?
C12A N11A C10A 106.5(9) . . ?
C12A N11A C11A 127.6(9) . . ?
C10A N11A C11A 125.9(9) . . ?
N11A C11A H11C 109.5 . . ?
N11A C11A H11B 109.5 . . ?
H11C C11A H11B 109.5 . . ?
N11A C11A H11A 109.5 . . ?
H11C C11A H11A 109.5 . . ?
H11B C11A H11A 109.5 . . ?
N11A C12A C13A 108.3(10) . . ?
N11A C12A H12A 125.8 . . ?
C13A C12A H12A 125.8 . . ?
C12A C13A N14A 108.7(9) . . ?
C12A C13A H13A 125.7 . . ?
N14A C13A H13A 125.7 . . ?
C10A N14A C13A 105.4(8) . . ?
C10A N14A Er1 117.4(6) . . ?
C13A N14A Er1 137.1(7) . . ?
O13B N1B O12B 122.8(9) . . ?
O13B N1B O11B 121.0(9) . . ?
O12B N1B O11B 116.1(8) . . ?
O13B N1B Er1 179.0(8) . . ?
O12B N1B Er1 56.3(5) . . ?
O11B N1B Er1 59.9(5) . . ?
N1B O11B Er1 93.4(5) . . ?
N1B O12B Er1 97.2(5) . . ?
O13C N1C O11C 124.3(9) . . ?
O13C N1C O12C 121.8(9) . . ?
O11C N1C O12C 113.9(8) . . ?
O13C N1C Er1 175.7(7) . . ?
O11C N1C Er1 56.7(5) . . ?
O12C N1C Er1 57.3(4) . . ?
N1C O11C Er1 97.5(6) . . ?
N1C O12C Er1 96.2(5) . . ?
O12D N1D O13D 122.9(9) . . ?
O12D N1D O11D 117.0(9) . . ?
O13D N1D O11D 120.1(9) . . ?
N1D O11D Er1 147.1(7) . . ?
Er1 O1E H1E1 115.6 . . ?
Er1 O1E H1E2 114.0 . . ?
H1E1 O1E H1E2 102.1 . . ?

_refine_diff_density_max         4.164
_refine_diff_density_min         -2.236
_refine_diff_density_rms         0.255

_shelxl_version_number           2013-4

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_23
_audit_block_doi                 10.5517/ccdc.csd.cc1k5v7t
_database_code_depnum_ccdc_archive 'CCDC 1435586'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/C7QI00727B 2018
_audit_update_record             
;
2015-11-06 deposited with the CCDC.	2024-07-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H16 N8 O10 Yb, C2 H4 N'
_chemical_formula_sum            'C14 H20 N9 O10 Yb'
_chemical_formula_weight         647.43

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Yb Yb -0.3850 5.5486 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.1752(5)
_cell_length_b                   11.5352(9)
_cell_length_c                   13.1045(10)
_cell_angle_alpha                66.989(7)
_cell_angle_beta                 72.978(6)
_cell_angle_gamma                85.535(5)
_cell_volume                     1086.69(15)
_cell_formula_units_Z            2
_cell_measurement_temperature    120(1)
_cell_measurement_reflns_used    246
_cell_measurement_theta_min      3.5590
_cell_measurement_theta_max      27.2570

_exptl_crystal_description       plate
_exptl_crystal_colour            pale-yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.979
_exptl_crystal_F_000             634
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.08
_exptl_absorpt_coefficient_mu    4.376
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.75121
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      120(1)
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Eos
_diffrn_detector_area_resol_mean 16.1544
_diffrn_measurement_method       ω-scan
_diffrn_reflns_number            4347
_diffrn_reflns_av_unetI/netI     0.0838
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.299
_diffrn_reflns_theta_max         28.158
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.823
_diffrn_measured_fraction_theta_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.823
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.823
_diffrn_reflns_point_group_measured_fraction_full 0.985
_reflns_number_total             4347
_reflns_number_gt                3960
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlis Pro (Agilent Technologies (2011))'
_computing_cell_refinement       'CrysAlis Pro (Agilent Technologies (2011))'
_computing_data_reduction        'CrysAlis Pro (Agilent Technologies (2011))'
_computing_structure_solution    'SIR92 (Altomare et al., 1993)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Mercury (MacRae et al., 2009)'
_computing_publication_material  'SHELXL-2013 (Sheldrick, 2013)'

_refine_special_details          
;
 Refined as a 2-component twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0900P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4347
_refine_ls_number_parameters     312
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0580
_refine_ls_R_factor_gt           0.0490
_refine_ls_wR_factor_ref         0.1615
_refine_ls_wR_factor_gt          0.1587
_refine_ls_goodness_of_fit_ref   1.390
_refine_ls_restrained_S_all      1.390
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Yb1 Yb 0.56520(3) 0.64456(3) 0.74683(2) 0.01111(16) Uani 1 1 d . . . . .
N1A N 0.3537(7) 0.5595(6) 0.6910(6) 0.0124(13) Uani 1 1 d . . . . .
C2A C 0.2214(10) 0.4830(7) 0.7709(7) 0.0161(16) Uani 1 1 d . . . . .
H2A H 0.2157 0.4574 0.8502 0.019 Uiso 1 1 calc R U . . .
C3A C 0.0942(10) 0.4397(8) 0.7441(7) 0.0177(16) Uani 1 1 d . . . . .
H3A H 0.0012 0.3876 0.8033 0.021 Uiso 1 1 calc R U . . .
C4A C 0.1051(10) 0.4746(7) 0.6271(7) 0.0164(16) Uani 1 1 d . . . . .
H4A H 0.0198 0.4451 0.6060 0.020 Uiso 1 1 calc R U . . .
C5A C 0.2380(10) 0.5507(8) 0.5440(7) 0.0168(16) Uani 1 1 d . . . . .
H5A H 0.2483 0.5737 0.4644 0.020 Uiso 1 1 calc R U . . .
C6A C 0.3613(9) 0.5952(7) 0.5787(7) 0.0117(15) Uani 1 1 d . . . . .
N7A N 0.4957(8) 0.6743(6) 0.4973(6) 0.0146(13) Uani 1 1 d . . . . .
C71A C 0.5109(10) 0.7321(8) 0.3740(7) 0.0179(16) Uani 1 1 d . . . . .
H71C H 0.6009 0.6919 0.3326 0.027 Uiso 1 1 calc R U . . .
H71B H 0.5404 0.8223 0.3450 0.027 Uiso 1 1 calc R U . . .
H71A H 0.4017 0.7211 0.3614 0.027 Uiso 1 1 calc R U . . .
N8A N 0.6204(8) 0.6992(7) 0.5361(6) 0.0140(14) Uani 1 1 d . . . . .
C9A C 0.7591(10) 0.7609(7) 0.4656(7) 0.0148(15) Uani 1 1 d . . . . .
H9A H 0.7825 0.7903 0.3839 0.018 Uiso 1 1 calc R U . . .
C10A C 0.8762(9) 0.7819(7) 0.5207(7) 0.0125(15) Uani 1 1 d . . . . .
N11A N 1.0297(8) 0.8482(6) 0.4634(6) 0.0139(13) Uani 1 1 d . . . . .
C11A C 1.1020(10) 0.9120(8) 0.3388(7) 0.0198(17) Uani 1 1 d . . . . .
H11C H 1.1341 0.8492 0.3040 0.030 Uiso 1 1 calc R U . . .
H11B H 1.2036 0.9633 0.3225 0.030 Uiso 1 1 calc R U . . .
H11A H 1.0167 0.9664 0.3060 0.030 Uiso 1 1 calc R U . . .
C12A C 1.1001(10) 0.8445(7) 0.5473(7) 0.0168(16) Uani 1 1 d . . . . .
H12A H 1.2070 0.8822 0.5352 0.020 Uiso 1 1 calc R U . . .
C13A C 0.9891(10) 0.7770(8) 0.6508(7) 0.0173(16) Uani 1 1 d . . . . .
H13A H 1.0058 0.7593 0.7241 0.021 Uiso 1 1 calc R U . . .
N14A N 0.8484(7) 0.7379(6) 0.6336(6) 0.0131(13) Uani 1 1 d . . . . .
N1B N 0.6323(8) 0.3843(6) 0.8038(6) 0.0165(14) Uani 1 1 d . . . . .
O11B O 0.5286(7) 0.4224(5) 0.8759(5) 0.0170(12) Uani 1 1 d . . . . .
O12B O 0.7072(7) 0.4704(5) 0.7065(5) 0.0172(11) Uani 1 1 d . . . . .
O13B O 0.6582(8) 0.2735(6) 0.8246(6) 0.0258(14) Uani 1 1 d . . . . .
N1C N 0.7034(8) 0.7157(7) 0.8911(6) 0.0173(14) Uani 1 1 d . . . . .
O11C O 0.6150(7) 0.7895(5) 0.8314(5) 0.0169(11) Uani 1 1 d . . . . .
O12C O 0.7155(7) 0.6046(5) 0.8871(5) 0.0169(11) Uani 1 1 d . . . . .
O13C O 0.7742(8) 0.7430(6) 0.9486(6) 0.0278(14) Uani 1 1 d . . . . .
N1D N 0.4261(9) 0.9224(6) 0.6580(6) 0.0179(14) Uani 1 1 d . . . . .
O11D O 0.3023(9) 0.9831(6) 0.6853(8) 0.043(2) Uani 1 1 d . . . . .
O12D O 0.3955(7) 0.8042(5) 0.6848(5) 0.0192(12) Uani 1 1 d . . . . .
O13D O 0.5704(8) 0.9676(7) 0.6088(6) 0.0317(15) Uani 1 1 d . . . . .
O1E O 0.3327(6) 0.6096(5) 0.9106(5) 0.0152(11) Uani 1 1 d . . . . .
H1E H 0.3213 0.5256 0.9664 0.018 Uiso 1 1 calc R U . . .
C1E C 0.2039(12) 0.6900(9) 0.9433(8) 0.030(2) Uani 1 1 d . . . . .
H1E3 H 0.1983 0.7640 0.8745 0.046 Uiso 1 1 calc R U . . .
H1E2 H 0.2324 0.7173 0.9984 0.046 Uiso 1 1 calc R U . . .
H1E1 H 0.0927 0.6438 0.9796 0.046 Uiso 1 1 calc R U . . .
N1F N 0.0782(12) 0.1318(9) 0.8518(8) 0.042(2) Uani 1 1 d . . . . .
C2F C 0.1814(13) 0.0834(9) 0.8951(8) 0.030(2) Uani 1 1 d . . . . .
C3F C 0.3138(14) 0.0218(11) 0.9497(11) 0.041(3) Uani 1 1 d . . . . .
H3F3 H 0.3878 -0.0225 0.9042 0.061 Uiso 1 1 calc R U . . .
H3F2 H 0.2601 -0.0388 1.0282 0.061 Uiso 1 1 calc R U . . .
H3F1 H 0.3824 0.0853 0.9533 0.061 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Yb1 O12D 2.251(5) . ?
Yb1 O1E 2.331(5) . ?
Yb1 O12C 2.381(5) . ?
Yb1 O12B 2.402(5) . ?
Yb1 N14A 2.419(6) . ?
Yb1 O11B 2.440(6) . ?
Yb1 O11C 2.451(5) . ?
Yb1 N1A 2.461(6) . ?
Yb1 N8A 2.486(7) . ?
Yb1 N1B 2.846(7) . ?
Yb1 N1C 2.851(7) . ?
N1A C2A 1.344(10) . ?
N1A C6A 1.348(10) . ?
C2A C3A 1.373(11) . ?
C2A H2A 0.9500 . ?
C3A C4A 1.401(11) . ?
C3A H3A 0.9500 . ?
C4A C5A 1.359(12) . ?
C4A H4A 0.9500 . ?
C5A C6A 1.420(10) . ?
C5A H5A 0.9500 . ?
C6A N7A 1.373(10) . ?
N7A N8A 1.358(9) . ?
N7A C71A 1.458(10) . ?
C71A H71C 0.9800 . ?
C71A H71B 0.9800 . ?
C71A H71A 0.9800 . ?
N8A C9A 1.282(11) . ?
C9A C10A 1.440(10) . ?
C9A H9A 0.9500 . ?
C10A N14A 1.317(10) . ?
C10A N11A 1.369(10) . ?
N11A C12A 1.368(10) . ?
N11A C11A 1.457(11) . ?
C11A H11C 0.9800 . ?
C11A H11B 0.9800 . ?
C11A H11A 0.9800 . ?
C12A C13A 1.354(11) . ?
C12A H12A 0.9500 . ?
C13A N14A 1.374(9) . ?
C13A H13A 0.9500 . ?
N1B O13B 1.213(9) . ?
N1B O11B 1.266(8) . ?
N1B O12B 1.278(9) . ?
N1C O13C 1.214(9) . ?
N1C O11C 1.254(9) . ?
N1C O12C 1.298(9) . ?
N1D O13D 1.211(9) . ?
N1D O11D 1.231(9) . ?
N1D O12D 1.294(8) . ?
O1E C1E 1.431(10) . ?
O1E H1E 0.9500 . ?
C1E H1E3 0.9800 . ?
C1E H1E2 0.9800 . ?
C1E H1E1 0.9800 . ?
N1F C2F 1.142(13) . ?
C2F C3F 1.457(14) . ?
C3F H3F3 0.9800 . ?
C3F H3F2 0.9800 . ?
C3F H3F1 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O12D Yb1 O1E 77.1(2) . . ?
O12D Yb1 O12C 129.25(19) . . ?
O1E Yb1 O12C 80.70(18) . . ?
O12D Yb1 O12B 142.7(2) . . ?
O1E Yb1 O12B 120.58(19) . . ?
O12C Yb1 O12B 87.65(18) . . ?
O12D Yb1 N14A 102.4(2) . . ?
O1E Yb1 N14A 149.0(2) . . ?
O12C Yb1 N14A 76.0(2) . . ?
O12B Yb1 N14A 78.8(2) . . ?
O12D Yb1 O11B 137.2(2) . . ?
O1E Yb1 O11B 68.61(18) . . ?
O12C Yb1 O11B 69.96(18) . . ?
O12B Yb1 O11B 52.79(18) . . ?
N14A Yb1 O11B 120.26(19) . . ?
O12D Yb1 O11C 77.33(18) . . ?
O1E Yb1 O11C 74.40(19) . . ?
O12C Yb1 O11C 52.80(18) . . ?
O12B Yb1 O11C 136.72(18) . . ?
N14A Yb1 O11C 75.3(2) . . ?
O11B Yb1 O11C 115.27(18) . . ?
O12D Yb1 N1A 73.9(2) . . ?
O1E Yb1 N1A 80.7(2) . . ?
O12C Yb1 N1A 145.2(2) . . ?
O12B Yb1 N1A 77.00(19) . . ?
N14A Yb1 N1A 129.4(2) . . ?
O11B Yb1 N1A 75.98(19) . . ?
O11C Yb1 N1A 145.38(19) . . ?
O12D Yb1 N8A 73.4(2) . . ?
O1E Yb1 N8A 138.8(2) . . ?
O12C Yb1 N8A 140.5(2) . . ?
O12B Yb1 N8A 73.1(2) . . ?
N14A Yb1 N8A 66.7(2) . . ?
O11B Yb1 N8A 118.3(2) . . ?
O11C Yb1 N8A 124.6(2) . . ?
N1A Yb1 N8A 64.0(2) . . ?
O12D Yb1 N1B 148.01(19) . . ?
O1E Yb1 N1B 94.4(2) . . ?
O12C Yb1 N1B 78.11(18) . . ?
O12B Yb1 N1B 26.5(2) . . ?
N14A Yb1 N1B 100.4(2) . . ?
O11B Yb1 N1B 26.30(19) . . ?
O11C Yb1 N1B 130.59(18) . . ?
N1A Yb1 N1B 74.33(19) . . ?
N8A Yb1 N1B 95.7(2) . . ?
O12D Yb1 N1C 103.12(19) . . ?
O1E Yb1 N1C 77.22(19) . . ?
O12C Yb1 N1C 26.86(19) . . ?
O12B Yb1 N1C 112.54(19) . . ?
N14A Yb1 N1C 72.7(2) . . ?
O11B Yb1 N1C 93.66(19) . . ?
O11C Yb1 N1C 25.99(19) . . ?
N1A Yb1 N1C 157.8(2) . . ?
N8A Yb1 N1C 137.1(2) . . ?
N1B Yb1 N1C 104.93(19) . . ?
C2A N1A C6A 118.0(6) . . ?
C2A N1A Yb1 121.4(5) . . ?
C6A N1A Yb1 120.5(5) . . ?
N1A C2A C3A 123.5(7) . . ?
N1A C2A H2A 118.2 . . ?
C3A C2A H2A 118.2 . . ?
C2A C3A C4A 118.3(7) . . ?
C2A C3A H3A 120.9 . . ?
C4A C3A H3A 120.9 . . ?
C5A C4A C3A 119.8(7) . . ?
C5A C4A H4A 120.1 . . ?
C3A C4A H4A 120.1 . . ?
C4A C5A C6A 118.7(7) . . ?
C4A C5A H5A 120.7 . . ?
C6A C5A H5A 120.7 . . ?
N1A C6A N7A 117.8(6) . . ?
N1A C6A C5A 121.7(7) . . ?
N7A C6A C5A 120.4(7) . . ?
N8A N7A C6A 116.9(6) . . ?
N8A N7A C71A 119.0(6) . . ?
C6A N7A C71A 124.1(6) . . ?
N7A C71A H71C 109.5 . . ?
N7A C71A H71B 109.5 . . ?
H71C C71A H71B 109.5 . . ?
N7A C71A H71A 109.5 . . ?
H71C C71A H71A 109.5 . . ?
H71B C71A H71A 109.5 . . ?
C9A N8A N7A 121.2(7) . . ?
C9A N8A Yb1 119.3(5) . . ?
N7A N8A Yb1 119.2(5) . . ?
N8A C9A C10A 114.3(7) . . ?
N8A C9A H9A 122.9 . . ?
C10A C9A H9A 122.9 . . ?
N14A C10A N11A 111.5(6) . . ?
N14A C10A C9A 123.6(7) . . ?
N11A C10A C9A 124.9(7) . . ?
C10A N11A C12A 106.0(7) . . ?
C10A N11A C11A 127.1(6) . . ?
C12A N11A C11A 127.0(7) . . ?
N11A C11A H11C 109.5 . . ?
N11A C11A H11B 109.5 . . ?
H11C C11A H11B 109.5 . . ?
N11A C11A H11A 109.5 . . ?
H11C C11A H11A 109.5 . . ?
H11B C11A H11A 109.5 . . ?
C13A C12A N11A 107.2(7) . . ?
C13A C12A H12A 126.4 . . ?
N11A C12A H12A 126.4 . . ?
C12A C13A N14A 109.6(7) . . ?
C12A C13A H13A 125.2 . . ?
N14A C13A H13A 125.2 . . ?
C10A N14A C13A 105.7(6) . . ?
C10A N14A Yb1 115.2(5) . . ?
C13A N14A Yb1 138.2(5) . . ?
O13B N1B O11B 122.5(7) . . ?
O13B N1B O12B 121.9(7) . . ?
O11B N1B O12B 115.6(6) . . ?
O13B N1B Yb1 177.4(5) . . ?
O11B N1B Yb1 58.6(4) . . ?
O12B N1B Yb1 57.0(3) . . ?
N1B O11B Yb1 95.1(4) . . ?
N1B O12B Yb1 96.5(4) . . ?
O13C N1C O11C 124.2(7) . . ?
O13C N1C O12C 121.0(7) . . ?
O11C N1C O12C 114.7(6) . . ?
O13C N1C Yb1 175.0(5) . . ?
O11C N1C Yb1 58.9(4) . . ?
O12C N1C Yb1 56.0(4) . . ?
N1C O11C Yb1 95.1(4) . . ?
N1C O12C Yb1 97.2(4) . . ?
O13D N1D O11D 123.6(7) . . ?
O13D N1D O12D 120.0(7) . . ?
O11D N1D O12D 116.4(7) . . ?
N1D O12D Yb1 126.6(4) . . ?
C1E O1E Yb1 132.5(5) . . ?
C1E O1E H1E 113.7 . . ?
Yb1 O1E H1E 113.7 . . ?
O1E C1E H1E3 109.5 . . ?
O1E C1E H1E2 109.5 . . ?
H1E3 C1E H1E2 109.5 . . ?
O1E C1E H1E1 109.5 . . ?
H1E3 C1E H1E1 109.5 . . ?
H1E2 C1E H1E1 109.5 . . ?
N1F C2F C3F 179.6(12) . . ?
C2F C3F H3F3 109.5 . . ?
C2F C3F H3F2 109.5 . . ?
H3F3 C3F H3F2 109.5 . . ?
C2F C3F H3F1 109.5 . . ?
H3F3 C3F H3F1 109.5 . . ?
H3F2 C3F H3F1 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6A N1A C2A C3A -0.1(10) . . . . ?
Yb1 N1A C2A C3A 175.6(6) . . . . ?
N1A C2A C3A C4A 1.7(11) . . . . ?
C2A C3A C4A C5A -0.9(11) . . . . ?
C3A C4A C5A C6A -1.3(11) . . . . ?
C2A N1A C6A N7A 179.4(6) . . . . ?
Yb1 N1A C6A N7A 3.7(8) . . . . ?
C2A N1A C6A C5A -2.3(10) . . . . ?
Yb1 N1A C6A C5A -178.0(5) . . . . ?
C4A C5A C6A N1A 3.0(11) . . . . ?
C4A C5A C6A N7A -178.8(7) . . . . ?
N1A C6A N7A N8A 6.9(9) . . . . ?
C5A C6A N7A N8A -171.4(6) . . . . ?
N1A C6A N7A C71A -172.8(7) . . . . ?
C5A C6A N7A C71A 8.9(10) . . . . ?
C6A N7A N8A C9A 172.6(7) . . . . ?
C71A N7A N8A C9A -7.7(10) . . . . ?
C6A N7A N8A Yb1 -14.2(8) . . . . ?
C71A N7A N8A Yb1 165.6(5) . . . . ?
N7A N8A C9A C10A 178.6(6) . . . . ?
Yb1 N8A C9A C10A 5.3(8) . . . . ?
N8A C9A C10A N14A 2.5(10) . . . . ?
N8A C9A C10A N11A -178.1(7) . . . . ?
N14A C10A N11A C12A -0.1(8) . . . . ?
C9A C10A N11A C12A -179.5(7) . . . . ?
N14A C10A N11A C11A -178.9(7) . . . . ?
C9A C10A N11A C11A 1.6(11) . . . . ?
C10A N11A C12A C13A 0.1(8) . . . . ?
C11A N11A C12A C13A 179.0(7) . . . . ?
N11A C12A C13A N14A -0.1(9) . . . . ?
N11A C10A N14A C13A 0.0(8) . . . . ?
C9A C10A N14A C13A 179.4(7) . . . . ?
N11A C10A N14A Yb1 171.6(4) . . . . ?
C9A C10A N14A Yb1 -9.0(9) . . . . ?
C12A C13A N14A C10A 0.1(8) . . . . ?
C12A C13A N14A Yb1 -168.4(5) . . . . ?
O13B N1B O11B Yb1 -177.2(6) . . . . ?
O12B N1B O11B Yb1 2.1(6) . . . . ?
O13B N1B O12B Yb1 177.2(6) . . . . ?
O11B N1B O12B Yb1 -2.1(6) . . . . ?
O13C N1C O11C Yb1 175.3(7) . . . . ?
O12C N1C O11C Yb1 -4.4(7) . . . . ?
O13C N1C O12C Yb1 -175.2(6) . . . . ?
O11C N1C O12C Yb1 4.5(7) . . . . ?
O13D N1D O12D Yb1 37.7(10) . . . . ?
O11D N1D O12D Yb1 -142.3(6) . . . . ?

_refine_diff_density_max         3.268
_refine_diff_density_min         -5.074
_refine_diff_density_rms         0.385

_shelxl_version_number           2013-4

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_06
_database_code_depnum_ccdc_archive 'CCDC 1005952'
_audit_update_record             
;
2016-01-10 deposited with the CCDC.	2024-07-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C25 H26 F9 Gd N10 O9 S3'
_chemical_formula_sum            'C25 H26 F9 Gd N10 O9 S3'
_chemical_formula_weight         1034.99

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Gd Gd -0.1653 3.9035 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x+1/2, y, z+1/2'
'x+1/2, -y, z'

_cell_length_a                   10.9002(6)
_cell_length_b                   17.0907(12)
_cell_length_c                   19.8139(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3691.2(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    2351
_cell_measurement_theta_min      3.2590
_cell_measurement_theta_max      27.9170

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.862
_exptl_crystal_F_000             2044
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_absorpt_coefficient_mu    2.075
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.44421
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     0.7107
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_detector_area_resol_mean 16.1544
_diffrn_measurement_method       ω-scan
_diffrn_reflns_number            9469
_diffrn_reflns_av_unetI/netI     0.0479
_diffrn_reflns_av_R_equivalents  0.0414
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         3.023
_diffrn_reflns_theta_max         24.994
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.843
_diffrn_reflns_point_group_measured_fraction_full 0.843
_reflns_number_total             5469
_reflns_number_gt                4714
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.639
_reflns_Friedel_fraction_max     0.680
_reflns_Friedel_fraction_full    0.680

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlis Pro (Agilent Technologies (2011))'
_computing_cell_refinement       'CrysAlis Pro (Agilent Technologies (2011))'
_computing_data_reduction        'CrysAlis Pro (Agilent Technologies (2011))'
_computing_structure_solution    'SIR92 (Altomare et al., 1993)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Mercury (MacRae et al., 2009)'
_computing_publication_material  'SHELXL-2013 (Sheldrick, 2013)'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0892P)²+16.1240P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1603 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.54(3)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         5469
_refine_ls_number_parameters     518
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0652
_refine_ls_R_factor_gt           0.0545
_refine_ls_wR_factor_ref         0.1565
_refine_ls_wR_factor_gt          0.1502
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_restrained_S_all      1.069
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Gd1 Gd 0.44285(5) 0.24237(3) 0.10027(9) 0.0269(2) Uani 1 1 d . . . . .
N1A N 0.4797(11) 0.1214(8) 0.0287(7) 0.033(3) Uani 1 1 d . . . . .
C2A C 0.4212(14) 0.0525(9) 0.0359(8) 0.035(3) Uani 1 1 d . . . . .
C3A C 0.4445(16) -0.0127(11) -0.0043(10) 0.048(4) Uani 1 1 d . . . . .
H3A H 0.4023 -0.0594 0.0023 0.058 Uiso 1 1 calc R U . . .
C4A C 0.5321(18) -0.0060(12) -0.0543(9) 0.053(5) Uani 1 1 d . . . . .
H4A H 0.5511 -0.0487 -0.0814 0.063 Uiso 1 1 calc R U . . .
C5A C 0.5902(16) 0.0631(12) -0.0636(9) 0.047(4) Uani 1 1 d . . . . .
H5A H 0.6480 0.0691 -0.0977 0.056 Uiso 1 1 calc R U . . .
C6A C 0.5621(15) 0.1241(10) -0.0216(9) 0.038(4) Uani 1 1 d . . . . .
H6A H 0.6033 0.1711 -0.0284 0.046 Uiso 1 1 calc R U . . .
N7A N 0.3281(11) 0.0509(7) 0.0849(6) 0.037(3) Uani 1 1 d . . . . .
C7A C 0.254(2) -0.0167(9) 0.0989(15) 0.065(5) Uani 1 1 d . . . . .
H7A1 H 0.2719 -0.0355 0.1435 0.097 Uiso 1 1 calc R U . . .
H7A2 H 0.2721 -0.0570 0.0666 0.097 Uiso 1 1 calc R U . . .
H7A3 H 0.1689 -0.0029 0.0960 0.097 Uiso 1 1 calc R U . . .
N8A N 0.3116(11) 0.1169(7) 0.1213(6) 0.030(3) Uani 1 1 d . . . . .
C9A C 0.2310(14) 0.1176(9) 0.1683(8) 0.035(4) Uani 1 1 d . . . . .
H9A H 0.1825 0.0742 0.1778 0.041 Uiso 1 1 calc R U . . .
C10A C 0.2199(15) 0.1910(12) 0.2061(10) 0.039(4) Uani 1 1 d . . . . .
N11A N 0.1543(15) 0.2015(10) 0.2621(8) 0.048(4) Uani 1 1 d . . . . .
C11A C 0.085(2) 0.1435(13) 0.3011(11) 0.065(6) Uani 1 1 d . . . . .
H11A H 0.0254 0.1190 0.2724 0.097 Uiso 1 1 calc R U . . .
H11B H 0.0444 0.1689 0.3380 0.097 Uiso 1 1 calc R U . . .
H11C H 0.1405 0.1045 0.3183 0.097 Uiso 1 1 calc R U . . .
C12A C 0.1741(19) 0.2763(12) 0.2831(11) 0.055(5) Uani 1 1 d . . . . .
H12A H 0.1400 0.3001 0.3209 0.065 Uiso 1 1 calc R U . . .
C13A C 0.2524(19) 0.3093(11) 0.2388(10) 0.054(5) Uani 1 1 d . . . . .
H13A H 0.2820 0.3603 0.2407 0.065 Uiso 1 1 calc R U . . .
N14A N 0.2814(16) 0.2534(7) 0.1894(9) 0.031(4) Uani 1 1 d . . . . .
N1B N 0.5100(13) 0.3609(9) 0.1673(7) 0.042(3) Uani 1 1 d . . . . .
C2B C 0.4526(16) 0.4321(9) 0.1637(9) 0.040(4) Uani 1 1 d . . . . .
C3B C 0.491(2) 0.4912(12) 0.2057(12) 0.065(6) Uani 1 1 d . . . . .
H3B H 0.4535 0.5399 0.2022 0.078 Uiso 1 1 calc R U . . .
C4B C 0.580(2) 0.4812(15) 0.2517(16) 0.091(9) Uani 1 1 d . . . . .
H4B H 0.6018 0.5216 0.2808 0.109 Uiso 1 1 calc R U . . .
C5B C 0.638(2) 0.4098(13) 0.2547(13) 0.074(7) Uani 1 1 d . . . . .
H5B H 0.7017 0.4014 0.2849 0.088 Uiso 1 1 calc R U . . .
C6B C 0.5996(16) 0.3523(11) 0.2132(9) 0.046(4) Uani 1 1 d . . . . .
H6B H 0.6377 0.3038 0.2166 0.055 Uiso 1 1 calc R U . . .
N7B N 0.3593(13) 0.4408(7) 0.1189(7) 0.043(4) Uani 1 1 d . . . . .
C7B C 0.310(2) 0.5163(9) 0.0978(18) 0.080(7) Uani 1 1 d . . . . .
H7B1 H 0.3271 0.5243 0.0508 0.119 Uiso 1 1 calc R U . . .
H7B2 H 0.3476 0.5572 0.1238 0.119 Uiso 1 1 calc R U . . .
H7B3 H 0.2229 0.5170 0.1050 0.119 Uiso 1 1 calc R U . . .
N8B N 0.3232(11) 0.3738(7) 0.0853(7) 0.038(4) Uani 1 1 d . . . . .
C9B C 0.2347(15) 0.3774(8) 0.0430(9) 0.037(4) Uani 1 1 d . . . . .
H9B H 0.1920 0.4236 0.0350 0.045 Uiso 1 1 calc R U . . .
C10B C 0.2049(14) 0.3059(9) 0.0084(9) 0.036(4) Uani 1 1 d . . . . .
N11B N 0.1221(14) 0.2980(9) -0.0412(9) 0.050(4) Uani 1 1 d . . . . .
C11B C 0.041(2) 0.3599(14) -0.0681(13) 0.076(7) Uani 1 1 d . . . . .
H11D H -0.0151 0.3376 -0.0999 0.114 Uiso 1 1 calc R U . . .
H11E H 0.0899 0.3992 -0.0901 0.114 Uiso 1 1 calc R U . . .
H11F H -0.0039 0.3833 -0.0317 0.114 Uiso 1 1 calc R U . . .
C12B C 0.131(2) 0.2229(15) -0.0632(12) 0.063(7) Uani 1 1 d . . . . .
H12B H 0.0865 0.2000 -0.0979 0.075 Uiso 1 1 calc R U . . .
C13B C 0.215(2) 0.1891(13) -0.0255(11) 0.058(6) Uani 1 1 d . . . . .
H13B H 0.2393 0.1371 -0.0298 0.069 Uiso 1 1 calc R U . . .
N14B N 0.2632(18) 0.2403(10) 0.0209(10) 0.047(5) Uani 1 1 d . . . . .
S1C S 0.7872(4) 0.2502(2) 0.0677(3) 0.0416(9) Uani 1 1 d . . . . .
O11C O 0.7991(14) 0.3297(8) 0.0530(9) 0.079(4) Uani 1 1 d . . . . .
O12C O 0.8276(13) 0.1959(9) 0.0167(8) 0.065(4) Uani 1 1 d . . . . .
O13C O 0.6718(8) 0.2287(7) 0.0972(10) 0.046(2) Uani 1 1 d . . . . .
C1C C 0.901(2) 0.2372(17) 0.1350(13) 0.072(7) Uani 1 1 d . . . . .
F11C F 0.9107(14) 0.1620(11) 0.1511(10) 0.116(7) Uani 1 1 d . . . . .
F12C F 0.8697(15) 0.2758(15) 0.1908(8) 0.124(7) Uani 1 1 d . . . . .
F13C F 1.0067(11) 0.2626(10) 0.1151(9) 0.103(7) Uani 1 1 d . . . . .
S1D S 0.5135(4) 0.1070(3) 0.2450(3) 0.0403(10) Uani 1 1 d . . . . .
O11D O 0.4183(12) 0.1119(10) 0.2935(7) 0.062(4) Uani 1 1 d . . . . .
O12D O 0.5288(15) 0.0323(9) 0.2122(9) 0.074(4) Uani 1 1 d . . . . .
O13D O 0.5199(11) 0.1717(8) 0.1979(7) 0.048(3) Uani 1 1 d . . . . .
C1D C 0.654(2) 0.122(2) 0.2952(15) 0.085(9) Uani 1 1 d . . . . .
F11D F 0.6595(15) 0.0630(17) 0.3388(11) 0.168(12) Uani 1 1 d . . . . .
F12D F 0.6476(18) 0.1845(17) 0.3268(12) 0.151(10) Uani 1 1 d . . . . .
F13D F 0.7522(12) 0.1195(13) 0.2588(8) 0.127(7) Uani 1 1 d . . . . .
S1E S 0.5083(4) 0.3825(3) -0.0391(3) 0.0444(10) Uani 1 1 d . . . . .
O11E O 0.5438(17) 0.4515(10) -0.0027(9) 0.082(5) Uani 1 1 d . . . . .
O12E O 0.3996(12) 0.3841(10) -0.0807(8) 0.072(5) Uani 1 1 d . . . . .
O13E O 0.5195(10) 0.3103(7) 0.0003(6) 0.045(3) Uani 1 1 d . . . . .
C1E C 0.627(2) 0.373(2) -0.0987(13) 0.083(8) Uani 1 1 d . . . . .
F11E F 0.619(2) 0.3079(19) -0.1334(12) 0.182(12) Uani 1 1 d . . . . .
F12E F 0.7343(12) 0.3785(15) -0.0789(9) 0.153(10) Uani 1 1 d . . . . .
F13E F 0.6147(17) 0.4258(17) -0.1485(11) 0.167(12) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Gd1 O13D 2.430(12) . ?
Gd1 O13E 2.443(12) . ?
Gd1 N14A 2.501(17) . ?
Gd1 O13C 2.507(9) . ?
Gd1 N14B 2.512(19) . ?
Gd1 N1B 2.530(15) . ?
Gd1 N1A 2.539(13) . ?
Gd1 N8A 2.611(12) . ?
Gd1 N8B 2.615(12) . ?
N1A C6A 1.34(2) . ?
N1A C2A 1.35(2) . ?
C2A C3A 1.39(2) . ?
C2A N7A 1.404(19) . ?
C3A C4A 1.38(2) . ?
C3A H3A 0.9300 . ?
C4A C5A 1.35(3) . ?
C4A H4A 0.9300 . ?
C5A C6A 1.37(2) . ?
C5A H5A 0.9300 . ?
C6A H6A 0.9300 . ?
N7A N8A 1.351(17) . ?
N7A C7A 1.44(2) . ?
C7A H7A1 0.9600 . ?
C7A H7A2 0.9600 . ?
C7A H7A3 0.9600 . ?
N8A C9A 1.280(19) . ?
C9A C10A 1.47(2) . ?
C9A H9A 0.9300 . ?
C10A N14A 1.30(2) . ?
C10A N11A 1.33(2) . ?
N11A C12A 1.36(3) . ?
N11A C11A 1.47(2) . ?
C11A H11A 0.9600 . ?
C11A H11B 0.9600 . ?
C11A H11C 0.9600 . ?
C12A C13A 1.35(3) . ?
C12A H12A 0.9300 . ?
C13A N14A 1.40(2) . ?
C13A H13A 0.9300 . ?
N1B C6B 1.34(2) . ?
N1B C2B 1.37(2) . ?
C2B N7B 1.36(2) . ?
C2B C3B 1.37(3) . ?
C3B C4B 1.34(3) . ?
C3B H3B 0.9300 . ?
C4B C5B 1.38(3) . ?
C4B H4B 0.9300 . ?
C5B C6B 1.35(3) . ?
C5B H5B 0.9300 . ?
C6B H6B 0.9300 . ?
N7B N8B 1.382(18) . ?
N7B C7B 1.46(2) . ?
C7B H7B1 0.9600 . ?
C7B H7B2 0.9600 . ?
C7B H7B3 0.9600 . ?
N8B C9B 1.28(2) . ?
C9B C10B 1.44(2) . ?
C9B H9B 0.9300 . ?
C10B N14B 1.31(2) . ?
C10B N11B 1.34(2) . ?
N11B C12B 1.36(3) . ?
N11B C11B 1.48(2) . ?
C11B H11D 0.9600 . ?
C11B H11E 0.9600 . ?
C11B H11F 0.9600 . ?
C12B C13B 1.32(3) . ?
C12B H12B 0.9300 . ?
C13B N14B 1.37(3) . ?
C13B H13B 0.9300 . ?
S1C O11C 1.395(14) . ?
S1C O13C 1.436(13) . ?
S1C O12C 1.441(15) . ?
S1C C1C 1.84(2) . ?
C1C F13C 1.29(3) . ?
C1C F11C 1.33(3) . ?
C1C F12C 1.33(3) . ?
S1D O11D 1.417(13) . ?
S1D O12D 1.441(16) . ?
S1D O13D 1.450(12) . ?
S1D C1D 1.84(2) . ?
C1D F12D 1.24(4) . ?
C1D F13D 1.29(3) . ?
C1D F11D 1.33(3) . ?
S1E O11E 1.434(18) . ?
S1E O12E 1.444(15) . ?
S1E O13E 1.465(13) . ?
S1E C1E 1.76(3) . ?
C1E F12E 1.24(3) . ?
C1E F11E 1.30(4) . ?
C1E F13E 1.35(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O13D Gd1 O13E 139.7(4) . . ?
O13D Gd1 N14A 73.7(5) . . ?
O13E Gd1 N14A 141.0(4) . . ?
O13D Gd1 O13C 68.2(5) . . ?
O13E Gd1 O13C 71.6(5) . . ?
N14A Gd1 O13C 136.4(6) . . ?
O13D Gd1 N14B 139.6(5) . . ?
O13E Gd1 N14B 76.4(5) . . ?
N14A Gd1 N14B 84.0(5) . . ?
O13C Gd1 N14B 139.4(6) . . ?
O13D Gd1 N1B 83.1(5) . . ?
O13E Gd1 N1B 86.9(4) . . ?
N14A Gd1 N1B 76.8(5) . . ?
O13C Gd1 N1B 78.4(4) . . ?
N14B Gd1 N1B 124.4(5) . . ?
O13D Gd1 N1A 89.2(4) . . ?
O13E Gd1 N1A 83.1(4) . . ?
N14A Gd1 N1A 124.6(4) . . ?
O13C Gd1 N1A 75.7(4) . . ?
N14B Gd1 N1A 76.2(5) . . ?
N1B Gd1 N1A 154.1(4) . . ?
O13D Gd1 N8A 69.8(4) . . ?
O13E Gd1 N8A 135.0(4) . . ?
N14A Gd1 N8A 64.1(4) . . ?
O13C Gd1 N8A 118.2(4) . . ?
N14B Gd1 N8A 70.2(4) . . ?
N1B Gd1 N8A 137.1(4) . . ?
N1A Gd1 N8A 60.5(4) . . ?
O13D Gd1 N8B 133.6(5) . . ?
O13E Gd1 N8B 70.8(4) . . ?
N14A Gd1 N8B 70.4(4) . . ?
O13C Gd1 N8B 125.0(4) . . ?
N14B Gd1 N8B 63.4(5) . . ?
N1B Gd1 N8B 61.1(4) . . ?
N1A Gd1 N8B 135.7(4) . . ?
N8A Gd1 N8B 116.8(3) . . ?
C6A N1A C2A 115.3(14) . . ?
C6A N1A Gd1 119.5(11) . . ?
C2A N1A Gd1 125.3(10) . . ?
N1A C2A C3A 123.5(15) . . ?
N1A C2A N7A 115.7(13) . . ?
C3A C2A N7A 120.7(14) . . ?
C4A C3A C2A 118.0(17) . . ?
C4A C3A H3A 121.0 . . ?
C2A C3A H3A 121.0 . . ?
C5A C4A C3A 119.6(17) . . ?
C5A C4A H4A 120.2 . . ?
C3A C4A H4A 120.2 . . ?
C4A C5A C6A 118.5(17) . . ?
C4A C5A H5A 120.8 . . ?
C6A C5A H5A 120.8 . . ?
N1A C6A C5A 125.1(17) . . ?
N1A C6A H6A 117.4 . . ?
C5A C6A H6A 117.4 . . ?
N8A N7A C2A 116.6(12) . . ?
N8A N7A C7A 119.6(14) . . ?
C2A N7A C7A 123.7(14) . . ?
N7A C7A H7A1 109.5 . . ?
N7A C7A H7A2 109.5 . . ?
H7A1 C7A H7A2 109.5 . . ?
N7A C7A H7A3 109.5 . . ?
H7A1 C7A H7A3 109.5 . . ?
H7A2 C7A H7A3 109.5 . . ?
C9A N8A N7A 119.1(12) . . ?
C9A N8A Gd1 119.0(10) . . ?
N7A N8A Gd1 121.8(9) . . ?
N8A C9A C10A 115.9(14) . . ?
N8A C9A H9A 122.1 . . ?
C10A C9A H9A 122.1 . . ?
N14A C10A N11A 112.1(18) . . ?
N14A C10A C9A 121.9(16) . . ?
N11A C10A C9A 125.9(17) . . ?
C10A N11A C12A 107.2(15) . . ?
C10A N11A C11A 128.5(17) . . ?
C12A N11A C11A 123.9(16) . . ?
N11A C11A H11A 109.5 . . ?
N11A C11A H11B 109.5 . . ?
H11A C11A H11B 109.5 . . ?
N11A C11A H11C 109.5 . . ?
H11A C11A H11C 109.5 . . ?
H11B C11A H11C 109.5 . . ?
C13A C12A N11A 107.2(16) . . ?
C13A C12A H12A 126.4 . . ?
N11A C12A H12A 126.4 . . ?
C12A C13A N14A 108.1(17) . . ?
C12A C13A H13A 125.9 . . ?
N14A C13A H13A 125.9 . . ?
C10A N14A C13A 105.4(17) . . ?
C10A N14A Gd1 118.6(12) . . ?
C13A N14A Gd1 134.6(12) . . ?
C6B N1B C2B 117.6(15) . . ?
C6B N1B Gd1 118.7(12) . . ?
C2B N1B Gd1 123.5(11) . . ?
N7B C2B N1B 118.2(14) . . ?
N7B C2B C3B 122.9(17) . . ?
N1B C2B C3B 118.9(18) . . ?
C4B C3B C2B 123(2) . . ?
C4B C3B H3B 118.7 . . ?
C2B C3B H3B 118.7 . . ?
C3B C4B C5B 118(2) . . ?
C3B C4B H4B 120.9 . . ?
C5B C4B H4B 120.9 . . ?
C6B C5B C4B 119(2) . . ?
C6B C5B H5B 120.7 . . ?
C4B C5B H5B 120.7 . . ?
N1B C6B C5B 124.0(19) . . ?
N1B C6B H6B 118.0 . . ?
C5B C6B H6B 118.0 . . ?
C2B N7B N8B 115.9(12) . . ?
C2B N7B C7B 124.1(15) . . ?
N8B N7B C7B 119.3(16) . . ?
N7B C7B H7B1 109.5 . . ?
N7B C7B H7B2 109.5 . . ?
H7B1 C7B H7B2 109.5 . . ?
N7B C7B H7B3 109.5 . . ?
H7B1 C7B H7B3 109.5 . . ?
H7B2 C7B H7B3 109.5 . . ?
C9B N8B N7B 119.4(12) . . ?
C9B N8B Gd1 119.4(10) . . ?
N7B N8B Gd1 121.0(9) . . ?
N8B C9B C10B 116.2(14) . . ?
N8B C9B H9B 121.9 . . ?
C10B C9B H9B 121.9 . . ?
N14B C10B N11B 112.2(16) . . ?
N14B C10B C9B 121.8(16) . . ?
N11B C10B C9B 125.9(15) . . ?
C10B N11B C12B 106.3(14) . . ?
C10B N11B C11B 126.4(17) . . ?
C12B N11B C11B 127.2(17) . . ?
N11B C11B H11D 109.5 . . ?
N11B C11B H11E 109.5 . . ?
H11D C11B H11E 109.5 . . ?
N11B C11B H11F 109.5 . . ?
H11D C11B H11F 109.5 . . ?
H11E C11B H11F 109.5 . . ?
C13B C12B N11B 106.6(17) . . ?
C13B C12B H12B 126.7 . . ?
N11B C12B H12B 126.7 . . ?
C12B C13B N14B 111(2) . . ?
C12B C13B H13B 124.4 . . ?
N14B C13B H13B 124.4 . . ?
C10B N14B C13B 103.6(18) . . ?
C10B N14B Gd1 118.9(13) . . ?
C13B N14B Gd1 136.4(15) . . ?
O11C S1C O13C 114.6(9) . . ?
O11C S1C O12C 116.8(10) . . ?
O13C S1C O12C 112.9(8) . . ?
O11C S1C C1C 102.0(11) . . ?
O13C S1C C1C 105.5(11) . . ?
O12C S1C C1C 103.0(11) . . ?
S1C O13C Gd1 149.1(11) . . ?
F13C C1C F11C 109(2) . . ?
F13C C1C F12C 108(2) . . ?
F11C C1C F12C 107(2) . . ?
F13C C1C S1C 109.9(17) . . ?
F11C C1C S1C 110.2(18) . . ?
F12C C1C S1C 111.6(17) . . ?
O11D S1D O12D 116.3(10) . . ?
O11D S1D O13D 115.3(9) . . ?
O12D S1D O13D 112.3(9) . . ?
O11D S1D C1D 103.6(12) . . ?
O12D S1D C1D 105.7(13) . . ?
O13D S1D C1D 101.6(10) . . ?
S1D O13D Gd1 151.1(7) . . ?
F12D C1D F13D 111(3) . . ?
F12D C1D F11D 109(3) . . ?
F13D C1D F11D 107(2) . . ?
F12D C1D S1D 110(2) . . ?
F13D C1D S1D 113(2) . . ?
F11D C1D S1D 106(2) . . ?
O11E S1E O12E 119.5(11) . . ?
O11E S1E O13E 113.7(9) . . ?
O12E S1E O13E 112.8(8) . . ?
O11E S1E C1E 102.6(14) . . ?
O12E S1E C1E 102.8(11) . . ?
O13E S1E C1E 102.4(11) . . ?
S1E O13E Gd1 143.4(8) . . ?
F12E C1E F11E 107(3) . . ?
F12E C1E F13E 106(2) . . ?
F11E C1E F13E 100(3) . . ?
F12E C1E S1E 118(2) . . ?
F11E C1E S1E 113(2) . . ?
F13E C1E S1E 111(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6A N1A C2A C3A 1(2) . . . . ?
Gd1 N1A C2A C3A -179.7(13) . . . . ?
C6A N1A C2A N7A -175.2(14) . . . . ?
Gd1 N1A C2A N7A 3.8(19) . . . . ?
N1A C2A C3A C4A 0(3) . . . . ?
N7A C2A C3A C4A 176.1(15) . . . . ?
C2A C3A C4A C5A -1(3) . . . . ?
C3A C4A C5A C6A 2(3) . . . . ?
C2A N1A C6A C5A -1(2) . . . . ?
Gd1 N1A C6A C5A 179.9(14) . . . . ?
C4A C5A C6A N1A 0(3) . . . . ?
N1A C2A N7A N8A -3.1(19) . . . . ?
C3A C2A N7A N8A -179.7(15) . . . . ?
N1A C2A N7A C7A 178.8(18) . . . . ?
C3A C2A N7A C7A 2(3) . . . . ?
C2A N7A N8A C9A -177.4(13) . . . . ?
C7A N7A N8A C9A 1(2) . . . . ?
C2A N7A N8A Gd1 1.2(16) . . . . ?
C7A N7A N8A Gd1 179.5(14) . . . . ?
N7A N8A C9A C10A 179.1(13) . . . . ?
Gd1 N8A C9A C10A 0.4(18) . . . . ?
N8A C9A C10A N14A 5(3) . . . . ?
N8A C9A C10A N11A -170.7(16) . . . . ?
N14A C10A N11A C12A 0(2) . . . . ?
C9A C10A N11A C12A 176.7(18) . . . . ?
N14A C10A N11A C11A -172(2) . . . . ?
C9A C10A N11A C11A 4(3) . . . . ?
C10A N11A C12A C13A 0(2) . . . . ?
C11A N11A C12A C13A 173(2) . . . . ?
N11A C12A C13A N14A 0(2) . . . . ?
N11A C10A N14A C13A 0(2) . . . . ?
C9A C10A N14A C13A -176.8(17) . . . . ?
N11A C10A N14A Gd1 168.2(12) . . . . ?
C9A C10A N14A Gd1 -8(2) . . . . ?
C12A C13A N14A C10A 0(2) . . . . ?
C12A C13A N14A Gd1 -165.6(15) . . . . ?
C6B N1B C2B N7B -178.0(15) . . . . ?
Gd1 N1B C2B N7B -4(2) . . . . ?
C6B N1B C2B C3B 1(2) . . . . ?
Gd1 N1B C2B C3B 175.4(14) . . . . ?
N7B C2B C3B C4B 177(2) . . . . ?
N1B C2B C3B C4B -2(3) . . . . ?
C2B C3B C4B C5B 2(4) . . . . ?
C3B C4B C5B C6B -2(4) . . . . ?
C2B N1B C6B C5B -1(3) . . . . ?
Gd1 N1B C6B C5B -175.7(17) . . . . ?
C4B C5B C6B N1B 2(4) . . . . ?
N1B C2B N7B N8B 6(2) . . . . ?
C3B C2B N7B N8B -173.4(17) . . . . ?
N1B C2B N7B C7B -165(2) . . . . ?
C3B C2B N7B C7B 16(3) . . . . ?
C2B N7B N8B C9B 179.1(14) . . . . ?
C7B N7B N8B C9B -10(2) . . . . ?
C2B N7B N8B Gd1 -5.5(17) . . . . ?
C7B N7B N8B Gd1 165.6(16) . . . . ?
N7B N8B C9B C10B 178.0(14) . . . . ?
Gd1 N8B C9B C10B 2.5(19) . . . . ?
N8B C9B C10B N14B 2(3) . . . . ?
N8B C9B C10B N11B -174.8(16) . . . . ?
N14B C10B N11B C12B -2(2) . . . . ?
C9B C10B N11B C12B 174.8(18) . . . . ?
N14B C10B N11B C11B -180(2) . . . . ?
C9B C10B N11B C11B -3(3) . . . . ?
C10B N11B C12B C13B 1(2) . . . . ?
C11B N11B C12B C13B 179(2) . . . . ?
N11B C12B C13B N14B 0(3) . . . . ?
N11B C10B N14B C13B 2(2) . . . . ?
C9B C10B N14B C13B -175.2(17) . . . . ?
N11B C10B N14B Gd1 171.8(12) . . . . ?
C9B C10B N14B Gd1 -5(2) . . . . ?
C12B C13B N14B C10B -1(3) . . . . ?
C12B C13B N14B Gd1 -168.2(18) . . . . ?
O11C S1C O13C Gd1 41(2) . . . . ?
O12C S1C O13C Gd1 -95.8(15) . . . . ?
C1C S1C O13C Gd1 152.6(17) . . . . ?
O11C S1C C1C F13C -54(2) . . . . ?
O13C S1C C1C F13C -173.7(17) . . . . ?
O12C S1C C1C F13C 68(2) . . . . ?
O11C S1C C1C F11C -174.1(18) . . . . ?
O13C S1C C1C F11C 65.9(19) . . . . ?
O12C S1C C1C F11C -53(2) . . . . ?
O11C S1C C1C F12C 67(2) . . . . ?
O13C S1C C1C F12C -53(2) . . . . ?
O12C S1C C1C F12C -171.9(19) . . . . ?
O11D S1D O13D Gd1 -75(2) . . . . ?
O12D S1D O13D Gd1 62(2) . . . . ?
C1D S1D O13D Gd1 174.3(19) . . . . ?
O11D S1D C1D F12D -56(2) . . . . ?
O12D S1D C1D F12D -178(2) . . . . ?
O13D S1D C1D F12D 64(2) . . . . ?
O11D S1D C1D F13D -180(2) . . . . ?
O12D S1D C1D F13D 57(2) . . . . ?
O13D S1D C1D F13D -60(2) . . . . ?
O11D S1D C1D F11D 63(3) . . . . ?
O12D S1D C1D F11D -60(3) . . . . ?
O13D S1D C1D F11D -177(2) . . . . ?
O11E S1E O13E Gd1 62.9(15) . . . . ?
O12E S1E O13E Gd1 -77.3(14) . . . . ?
C1E S1E O13E Gd1 172.9(14) . . . . ?
O11E S1E C1E F12E 47(3) . . . . ?
O12E S1E C1E F12E 172(3) . . . . ?
O13E S1E C1E F12E -71(3) . . . . ?
O11E S1E C1E F11E 173(2) . . . . ?
O12E S1E C1E F11E -62(2) . . . . ?
O13E S1E C1E F11E 55(2) . . . . ?
O11E S1E C1E F13E -75(3) . . . . ?
O12E S1E C1E F13E 50(3) . . . . ?
O13E S1E C1E F13E 167(2) . . . . ?

_refine_diff_density_max         1.090
_refine_diff_density_min         -0.803
_refine_diff_density_rms         0.120

_shelxl_version_number           2013-4

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_19
_database_code_depnum_ccdc_archive 'CCDC 1006326'
_audit_update_record             
;
2016-01-10 deposited with the CCDC.	2024-07-03 downloaded from the CCDC.
;


_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C11 H15 Dy N8 O10, C H4 O'
_chemical_formula_sum            'C12 H19 Dy N8 O11'
_chemical_formula_weight         613.85

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Dy Dy -0.1892 4.4098 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.2029(7)
_cell_length_b                   10.4813(9)
_cell_length_c                   12.4024(7)
_cell_angle_alpha                97.826(6)
_cell_angle_beta                 96.891(6)
_cell_angle_gamma                100.152(7)
_cell_volume                     1028.45(14)
_cell_formula_units_Z            2
_cell_measurement_temperature    291(2)
_cell_measurement_reflns_used    4715
_cell_measurement_theta_min      3.3280
_cell_measurement_theta_max      27.9000

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.982
_exptl_crystal_F_000             602
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.1
_exptl_absorpt_coefficient_mu    3.707
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.79442
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      291(2)
_diffrn_radiation_wavelength     0.7107
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_detector_area_resol_mean 16.1544
_diffrn_measurement_method       ω-scan
_diffrn_reflns_number            7224
_diffrn_reflns_av_unetI/netI     0.0292
_diffrn_reflns_av_R_equivalents  0.0168
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.917
_diffrn_reflns_theta_max         28.138
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.837
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.837
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.837
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4207
_reflns_number_gt                3955
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlis Pro (Agilent Technologies (2011))'
_computing_cell_refinement       'CrysAlis Pro (Agilent Technologies (2011))'
_computing_data_reduction        'CrysAlis Pro (Agilent Technologies (2011))'
_computing_structure_solution    'SIR92 (Altomare et al., 1993)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Mercury (MacRae et al., 2009)'
_computing_publication_material  'SHELXL-2013 (Sheldrick, 2013)'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0208P)²+0.4657P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4207
_refine_ls_number_parameters     301
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0240
_refine_ls_R_factor_gt           0.0214
_refine_ls_wR_factor_ref         0.0494
_refine_ls_wR_factor_gt          0.0483
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.056
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Dy1 Dy 0.70552(2) 0.23116(2) 0.71160(2) 0.02723(5) Uani 1 1 d . . . . .
N1A N 0.9549(3) 0.3004(2) 0.61923(19) 0.0304(5) Uani 1 1 d . . . . .
C2A C 1.0358(4) 0.4260(3) 0.6348(2) 0.0292(6) Uani 1 1 d . . . . .
C3A C 1.1771(4) 0.4640(3) 0.5859(3) 0.0391(7) Uani 1 1 d . . . . .
H3A H 1.2297 0.5518 0.5962 0.047 Uiso 1 1 calc R U . . .
C4A C 1.2378(4) 0.3705(4) 0.5224(3) 0.0448(8) Uani 1 1 d . . . . .
H4A H 1.3311 0.3945 0.4884 0.054 Uiso 1 1 calc R U . . .
C5A C 1.1592(4) 0.2408(4) 0.5094(3) 0.0461(8) Uani 1 1 d . . . . .
H5A H 1.2001 0.1753 0.4687 0.055 Uiso 1 1 calc R U . . .
C6A C 1.0201(4) 0.2113(3) 0.5576(3) 0.0395(7) Uani 1 1 d . . . . .
H6A H 0.9661 0.1238 0.5476 0.047 Uiso 1 1 calc R U . . .
N7A N 0.9715(3) 0.5170(2) 0.7004(2) 0.0328(6) Uani 1 1 d . . . . .
C7A C 1.0524(4) 0.6558(3) 0.7289(3) 0.0432(8) Uani 1 1 d . . . . .
H7A3 H 1.0012 0.7053 0.6795 0.065 Uiso 1 1 calc R U . . .
H7A2 H 1.1693 0.6650 0.7228 0.065 Uiso 1 1 calc R U . . .
H7A1 H 1.0398 0.6881 0.8030 0.065 Uiso 1 1 calc R U . . .
N8A N 0.8215(3) 0.4741(2) 0.73128(19) 0.0274(5) Uani 1 1 d . . . . .
C9A C 0.7388(4) 0.5552(3) 0.7755(2) 0.0324(7) Uani 1 1 d . . . . .
H9A H 0.7789 0.6454 0.7880 0.039 Uiso 1 1 calc R U . . .
C10A C 0.5808(4) 0.4987(3) 0.8046(2) 0.0323(7) Uani 1 1 d . . . . .
N11A N 0.4791(3) 0.5645(3) 0.8586(2) 0.0355(6) Uani 1 1 d . . . . .
C11A C 0.5086(5) 0.7054(3) 0.8985(3) 0.0502(9) Uani 1 1 d . . . . .
H11C H 0.6217 0.7347 0.9351 0.075 Uiso 1 1 calc R U . . .
H11B H 0.4326 0.7230 0.9493 0.075 Uiso 1 1 calc R U . . .
H11A H 0.4908 0.7512 0.8375 0.075 Uiso 1 1 calc R U . . .
C12A C 0.3436(4) 0.4735(3) 0.8697(3) 0.0407(8) Uani 1 1 d . . . . .
H12A H 0.2528 0.4895 0.9040 0.049 Uiso 1 1 calc R U . . .
C13A C 0.3664(4) 0.3561(3) 0.8214(3) 0.0394(7) Uani 1 1 d . . . . .
H13A H 0.2920 0.2769 0.8165 0.047 Uiso 1 1 calc R U . . .
N14A N 0.5150(3) 0.3705(2) 0.7807(2) 0.0339(6) Uani 1 1 d . . . . .
N1B N 0.5965(3) 0.2222(3) 0.4747(2) 0.0417(7) Uani 1 1 d . . . . .
O11B O 0.5529(4) 0.2236(3) 0.3775(2) 0.0705(9) Uani 1 1 d . . . . .
O12B O 0.6404(3) 0.1222(2) 0.50927(18) 0.0439(6) Uani 1 1 d . . . . .
O13B O 0.6018(3) 0.3206(2) 0.54766(18) 0.0398(5) Uani 1 1 d . . . . .
N1C N 0.7692(4) -0.0172(3) 0.7707(3) 0.0531(8) Uani 1 1 d . . . . .
O11C O 0.8122(5) -0.1151(3) 0.7978(3) 0.0903(11) Uani 1 1 d . . . . .
O12C O 0.6875(3) 0.0492(3) 0.8313(2) 0.0538(6) Uani 1 1 d . . . . .
O13C O 0.8019(4) 0.0231(2) 0.6857(2) 0.0575(7) Uani 1 1 d . . . . .
N1D N 0.9260(4) 0.3013(3) 0.9251(2) 0.0491(7) Uani 1 1 d . . . . .
O11D O 1.0214(4) 0.3272(4) 1.0110(2) 0.1005(13) Uani 1 1 d . . . . .
O12D O 0.9713(3) 0.2575(3) 0.83629(19) 0.0506(6) Uani 1 1 d . . . . .
O13D O 0.7776(3) 0.3179(3) 0.9181(2) 0.0533(6) Uani 1 1 d . . . . .
O1E O 0.4346(3) 0.0951(3) 0.6679(3) 0.0473(6) Uani 1 1 d . . . . .
H1E2 H 0.425(5) 0.029(4) 0.617(3) 0.056(12) Uiso 1 1 d . . . . .
H1E1 H 0.386(5) 0.073(4) 0.713(3) 0.053(13) Uiso 1 1 d . . . . .
C1F C 0.2286(8) -0.0052(5) 0.9020(4) 0.106(2) Uani 1 1 d . . . . .
H1F3 H 0.3464 0.0020 0.9245 0.159 Uiso 1 1 calc R U . . .
H1F2 H 0.1699 -0.0898 0.9111 0.159 Uiso 1 1 calc R U . . .
H1F1 H 0.1892 0.0622 0.9463 0.159 Uiso 1 1 calc R U . . .
O1F O 0.1999(5) 0.0096(5) 0.7917(3) 0.1081(13) Uani 1 1 d . . . . .
H1F H 0.0998 0.0065 0.7732 0.162 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Dy1 O1E 2.377(3) . ?
Dy1 O13C 2.442(2) . ?
Dy1 O12D 2.466(2) . ?
Dy1 N14A 2.469(2) . ?
Dy1 O13B 2.474(2) . ?
Dy1 N1A 2.508(2) . ?
Dy1 N8A 2.524(2) . ?
Dy1 O13D 2.559(2) . ?
Dy1 O12B 2.563(2) . ?
Dy1 O12C 2.567(2) . ?
Dy1 N1C 2.914(3) . ?
Dy1 N1D 2.946(3) . ?
N1A C2A 1.343(4) . ?
N1A C6A 1.349(4) . ?
C2A N7A 1.385(4) . ?
C2A C3A 1.393(4) . ?
C3A C4A 1.373(5) . ?
C3A H3A 0.9300 . ?
C4A C5A 1.377(5) . ?
C4A H4A 0.9300 . ?
C5A C6A 1.359(5) . ?
C5A H5A 0.9300 . ?
C6A H6A 0.9300 . ?
N7A N8A 1.352(3) . ?
N7A C7A 1.465(4) . ?
C7A H7A3 0.9600 . ?
C7A H7A2 0.9600 . ?
C7A H7A1 0.9600 . ?
N8A C9A 1.285(4) . ?
C9A C10A 1.435(4) . ?
C9A H9A 0.9300 . ?
C10A N14A 1.335(4) . ?
C10A N11A 1.353(4) . ?
N11A C12A 1.365(4) . ?
N11A C11A 1.460(4) . ?
C11A H11C 0.9600 . ?
C11A H11B 0.9600 . ?
C11A H11A 0.9600 . ?
C12A C13A 1.347(4) . ?
C12A H12A 0.9300 . ?
C13A N14A 1.365(4) . ?
C13A H13A 0.9300 . ?
N1B O11B 1.219(3) . ?
N1B O13B 1.267(3) . ?
N1B O12B 1.277(4) . ?
N1C O11C 1.218(4) . ?
N1C O13C 1.229(4) . ?
N1C O12C 1.281(4) . ?
N1D O11D 1.211(4) . ?
N1D O13D 1.254(4) . ?
N1D O12D 1.258(4) . ?
O1E H1E2 0.85(4) . ?
O1E H1E1 0.76(4) . ?
C1F O1F 1.394(6) . ?
C1F H1F3 0.9600 . ?
C1F H1F2 0.9600 . ?
C1F H1F1 0.9600 . ?
O1F H1F 0.8200 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1E Dy1 O13C 83.92(10) . . ?
O1E Dy1 O12D 140.86(10) . . ?
O13C Dy1 O12D 72.29(10) . . ?
O1E Dy1 N14A 75.14(9) . . ?
O13C Dy1 N14A 152.01(9) . . ?
O12D Dy1 N14A 113.59(8) . . ?
O1E Dy1 O13B 81.33(9) . . ?
O13C Dy1 O13B 118.95(8) . . ?
O12D Dy1 O13B 137.37(8) . . ?
N14A Dy1 O13B 76.43(8) . . ?
O1E Dy1 N1A 139.05(9) . . ?
O13C Dy1 N1A 80.91(8) . . ?
O12D Dy1 N1A 67.96(8) . . ?
N14A Dy1 N1A 127.03(8) . . ?
O13B Dy1 N1A 73.43(8) . . ?
O1E Dy1 N8A 135.51(9) . . ?
O13C Dy1 N8A 139.29(9) . . ?
O12D Dy1 N8A 77.52(8) . . ?
N14A Dy1 N8A 66.35(8) . . ?
O13B Dy1 N8A 69.00(7) . . ?
N1A Dy1 N8A 62.54(8) . . ?
O1E Dy1 O13D 111.31(10) . . ?
O13C Dy1 O13D 105.39(9) . . ?
O12D Dy1 O13D 50.02(8) . . ?
N14A Dy1 O13D 66.67(8) . . ?
O13B Dy1 O13D 135.14(8) . . ?
N1A Dy1 O13D 109.35(8) . . ?
N8A Dy1 O13D 73.28(8) . . ?
O1E Dy1 O12B 67.61(9) . . ?
O13C Dy1 O12B 68.92(9) . . ?
O12D Dy1 O12B 127.01(8) . . ?
N14A Dy1 O12B 117.74(8) . . ?
O13B Dy1 O12B 50.67(7) . . ?
N1A Dy1 O12B 71.44(8) . . ?
N8A Dy1 O12B 111.66(7) . . ?
O13D Dy1 O12B 174.19(8) . . ?
O1E Dy1 O12C 70.94(9) . . ?
O13C Dy1 O12C 50.52(8) . . ?
O12D Dy1 O12C 69.94(8) . . ?
N14A Dy1 O12C 104.13(9) . . ?
O13B Dy1 O12C 150.83(8) . . ?
N1A Dy1 O12C 123.04(8) . . ?
N8A Dy1 O12C 138.68(8) . . ?
O13D Dy1 O12C 66.45(8) . . ?
O12B Dy1 O12C 108.13(8) . . ?
O1E Dy1 N1C 77.96(9) . . ?
O13C Dy1 N1C 24.55(9) . . ?
O12D Dy1 N1C 67.42(9) . . ?
N14A Dy1 N1C 129.74(10) . . ?
O13B Dy1 N1C 139.26(8) . . ?
N1A Dy1 N1C 100.83(9) . . ?
N8A Dy1 N1C 144.89(8) . . ?
O13D Dy1 N1C 85.31(9) . . ?
O12B Dy1 N1C 88.89(9) . . ?
O12C Dy1 N1C 26.06(9) . . ?
O1E Dy1 N1D 128.62(10) . . ?
O13C Dy1 N1D 88.36(9) . . ?
O12D Dy1 N1D 24.92(8) . . ?
N14A Dy1 N1D 90.38(9) . . ?
O13B Dy1 N1D 143.32(8) . . ?
N1A Dy1 N1D 88.79(8) . . ?
N8A Dy1 N1D 74.34(8) . . ?
O13D Dy1 N1D 25.11(8) . . ?
O12B Dy1 N1D 151.58(9) . . ?
O12C Dy1 N1D 65.35(8) . . ?
N1C Dy1 N1D 74.64(9) . . ?
C2A N1A C6A 117.2(3) . . ?
C2A N1A Dy1 121.53(19) . . ?
C6A N1A Dy1 121.1(2) . . ?
N1A C2A N7A 117.2(3) . . ?
N1A C2A C3A 121.6(3) . . ?
N7A C2A C3A 121.2(3) . . ?
C4A C3A C2A 119.4(3) . . ?
C4A C3A H3A 120.3 . . ?
C2A C3A H3A 120.3 . . ?
C3A C4A C5A 119.4(3) . . ?
C3A C4A H4A 120.3 . . ?
C5A C4A H4A 120.3 . . ?
C6A C5A C4A 118.0(3) . . ?
C6A C5A H5A 121.0 . . ?
C4A C5A H5A 121.0 . . ?
N1A C6A C5A 124.4(3) . . ?
N1A C6A H6A 117.8 . . ?
C5A C6A H6A 117.8 . . ?
N8A N7A C2A 116.7(2) . . ?
N8A N7A C7A 120.3(2) . . ?
C2A N7A C7A 122.8(3) . . ?
N7A C7A H7A3 109.5 . . ?
N7A C7A H7A2 109.5 . . ?
H7A3 C7A H7A2 109.5 . . ?
N7A C7A H7A1 109.5 . . ?
H7A3 C7A H7A1 109.5 . . ?
H7A2 C7A H7A1 109.5 . . ?
C9A N8A N7A 121.0(2) . . ?
C9A N8A Dy1 118.6(2) . . ?
N7A N8A Dy1 120.27(17) . . ?
N8A C9A C10A 116.2(3) . . ?
N8A C9A H9A 121.9 . . ?
C10A C9A H9A 121.9 . . ?
N14A C10A N11A 110.8(3) . . ?
N14A C10A C9A 123.1(3) . . ?
N11A C10A C9A 126.1(3) . . ?
C10A N11A C12A 106.8(3) . . ?
C10A N11A C11A 126.9(3) . . ?
C12A N11A C11A 126.3(3) . . ?
N11A C11A H11C 109.5 . . ?
N11A C11A H11B 109.5 . . ?
H11C C11A H11B 109.5 . . ?
N11A C11A H11A 109.5 . . ?
H11C C11A H11A 109.5 . . ?
H11B C11A H11A 109.5 . . ?
C13A C12A N11A 106.9(3) . . ?
C13A C12A H12A 126.5 . . ?
N11A C12A H12A 126.5 . . ?
C12A C13A N14A 110.0(3) . . ?
C12A C13A H13A 125.0 . . ?
N14A C13A H13A 125.0 . . ?
C10A N14A C13A 105.4(3) . . ?
C10A N14A Dy1 114.9(2) . . ?
C13A N14A Dy1 138.5(2) . . ?
O11B N1B O13B 121.8(3) . . ?
O11B N1B O12B 122.2(3) . . ?
O13B N1B O12B 116.0(3) . . ?
N1B O12B Dy1 94.40(17) . . ?
N1B O13B Dy1 98.96(18) . . ?
O11C N1C O13C 122.5(4) . . ?
O11C N1C O12C 120.5(4) . . ?
O13C N1C O12C 117.0(3) . . ?
O11C N1C Dy1 173.6(3) . . ?
O13C N1C Dy1 55.66(16) . . ?
O12C N1C Dy1 61.68(16) . . ?
N1C O12C Dy1 92.26(19) . . ?
N1C O13C Dy1 99.8(2) . . ?
O11D N1D O13D 122.7(4) . . ?
O11D N1D O12D 121.7(4) . . ?
O13D N1D O12D 115.6(3) . . ?
O11D N1D Dy1 177.2(3) . . ?
O13D N1D Dy1 59.96(16) . . ?
O12D N1D Dy1 55.70(15) . . ?
N1D O12D Dy1 99.39(19) . . ?
N1D O13D Dy1 94.93(19) . . ?
Dy1 O1E H1E2 115(3) . . ?
Dy1 O1E H1E1 121(3) . . ?
H1E2 O1E H1E1 108(4) . . ?
O1F C1F H1F3 109.5 . . ?
O1F C1F H1F2 109.5 . . ?
H1F3 C1F H1F2 109.5 . . ?
O1F C1F H1F1 109.5 . . ?
H1F3 C1F H1F1 109.5 . . ?
H1F2 C1F H1F1 109.5 . . ?
C1F O1F H1F 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6A N1A C2A N7A -178.4(3) . . . . ?
Dy1 N1A C2A N7A -2.7(3) . . . . ?
C6A N1A C2A C3A 2.6(4) . . . . ?
Dy1 N1A C2A C3A 178.2(2) . . . . ?
N1A C2A C3A C4A -1.6(4) . . . . ?
N7A C2A C3A C4A 179.4(3) . . . . ?
C2A C3A C4A C5A -0.8(5) . . . . ?
C3A C4A C5A C6A 2.1(5) . . . . ?
C2A N1A C6A C5A -1.2(5) . . . . ?
Dy1 N1A C6A C5A -176.9(2) . . . . ?
C4A C5A C6A N1A -1.2(5) . . . . ?
N1A C2A N7A N8A -8.1(4) . . . . ?
C3A C2A N7A N8A 170.9(3) . . . . ?
N1A C2A N7A C7A 176.6(3) . . . . ?
C3A C2A N7A C7A -4.3(4) . . . . ?
C2A N7A N8A C9A -167.9(3) . . . . ?
C7A N7A N8A C9A 7.5(4) . . . . ?
C2A N7A N8A Dy1 15.2(3) . . . . ?
C7A N7A N8A Dy1 -169.4(2) . . . . ?
N7A N8A C9A C10A 179.7(2) . . . . ?
Dy1 N8A C9A C10A -3.3(3) . . . . ?
N8A C9A C10A N14A -4.8(4) . . . . ?
N8A C9A C10A N11A 175.1(3) . . . . ?
N14A C10A N11A C12A 0.3(3) . . . . ?
C9A C10A N11A C12A -179.6(3) . . . . ?
N14A C10A N11A C11A 179.7(3) . . . . ?
C9A C10A N11A C11A -0.2(5) . . . . ?
C10A N11A C12A C13A -0.5(3) . . . . ?
C11A N11A C12A C13A 180.0(3) . . . . ?
N11A C12A C13A N14A 0.6(4) . . . . ?
N11A C10A N14A C13A 0.1(3) . . . . ?
C9A C10A N14A C13A -180.0(3) . . . . ?
N11A C10A N14A Dy1 -169.78(18) . . . . ?
C9A C10A N14A Dy1 10.1(4) . . . . ?
C12A C13A N14A C10A -0.4(4) . . . . ?
C12A C13A N14A Dy1 165.6(2) . . . . ?
O11B N1B O12B Dy1 178.9(3) . . . . ?
O13B N1B O12B Dy1 -0.7(3) . . . . ?
O11B N1B O13B Dy1 -178.9(3) . . . . ?
O12B N1B O13B Dy1 0.7(3) . . . . ?
O11C N1C O12C Dy1 173.1(3) . . . . ?
O13C N1C O12C Dy1 -6.5(3) . . . . ?
O11C N1C O13C Dy1 -172.7(3) . . . . ?
O12C N1C O13C Dy1 6.9(3) . . . . ?
O11D N1D O12D Dy1 179.1(3) . . . . ?
O13D N1D O12D Dy1 -1.9(3) . . . . ?
O11D N1D O13D Dy1 -179.2(3) . . . . ?
O12D N1D O13D Dy1 1.8(3) . . . . ?

_refine_diff_density_max         0.598
_refine_diff_density_min         -0.473
_refine_diff_density_rms         0.079

_shelxl_version_number           2013-4

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_10
_audit_block_doi                 10.5517/ccdc.csd.cc14b09s
_database_code_depnum_ccdc_archive 'CCDC 1052304'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/C7QI00727B 2018
_audit_update_record             
;
2016-01-10 deposited with the CCDC.	2024-07-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C25 H34 Er F3 N10 O5 S, 2(C F3 O3 S)'
_chemical_formula_sum            'C27 H34 Er F9 N10 O11 S3'
_chemical_formula_weight         1109.08

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Er Er -0.2586 4.9576 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   10.9049(4)
_cell_length_b                   15.0238(4)
_cell_length_c                   27.3563(9)
_cell_angle_alpha                90
_cell_angle_beta                 100.350(4)
_cell_angle_gamma                90
_cell_volume                     4408.9(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(1)
_cell_measurement_reflns_used    5812
_cell_measurement_theta_min      3.3020
_cell_measurement_theta_max      28.1440

_exptl_crystal_description       plate
_exptl_crystal_colour            pale-yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.671
_exptl_crystal_F_000             2204
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.1
_exptl_absorpt_coefficient_mu    2.145
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.74179
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(1)
_diffrn_radiation_wavelength     0.7107
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_detector_area_resol_mean 16.1544
_diffrn_measurement_method       ω-scan

_diffrn_reflns_number            18023
_diffrn_reflns_av_unetI/netI     0.0496
_diffrn_reflns_av_R_equivalents  0.0463
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_theta_min         2.961
_diffrn_reflns_theta_max         28.269
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.840
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.840
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.840
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             9184
_reflns_number_gt                8353
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlis Pro (Agilent Technologies (2011))'
_computing_cell_refinement       'CrysAlis Pro (Agilent Technologies (2011))'
_computing_data_reduction        'CrysAlis Pro (Agilent Technologies (2011))'
_computing_structure_solution    'SIR92 (Altomare et al., 1993)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Mercury (MacRae et al., 2009)'
_computing_publication_material  'SHELXL-2013 (Sheldrick, 2013)'

_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0635P)²+58.0731P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         9184
_refine_ls_number_parameters     556
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0754
_refine_ls_R_factor_gt           0.0701
_refine_ls_wR_factor_ref         0.1731
_refine_ls_wR_factor_gt          0.1698
_refine_ls_goodness_of_fit_ref   1.124
_refine_ls_restrained_S_all      1.128
_refine_ls_shift/su_max          0.019
_refine_ls_shift/su_mean         0.000

# SQUEEZE RESULTS (APPEND TO CIF)
# Note: Data are Listed for all Voids in the P1 Unit Cell
# i.e. Centre of Gravity, Solvent Accessible Volume,
# Recovered number of Electrons in the Void and
# Details about the Squeezed Material
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.000 1.000 0.500 283 39 ' '
2 0.500 0.500 1.000 283 39 ' '
_platon_squeeze_details          
;
;

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Er1 Er 0.09708(3) 0.17897(2) 0.15225(2) 0.01705(12) Uani 1 1 d . . . . .
N1A N -0.0764(6) 0.1844(5) 0.0778(3) 0.0274(14) Uani 1 1 d . . . . .
C2A C -0.1944(7) 0.1576(6) 0.0791(3) 0.0323(19) Uani 1 1 d . . . . .
C3A C -0.2882(9) 0.1599(9) 0.0366(4) 0.055(3) Uani 1 1 d . . . . .
H3A H -0.3705 0.1405 0.0380 0.066 Uiso 1 1 calc R U . . .
C4A C -0.2580(10) 0.1909(12) -0.0067(4) 0.080(5) Uani 1 1 d . . . . .
H4A H -0.3200 0.1930 -0.0360 0.096 Uiso 1 1 calc R U . . .
C5A C -0.1382(9) 0.2194(12) -0.0085(4) 0.071(4) Uani 1 1 d . . . . .
H5A H -0.1168 0.2410 -0.0385 0.085 Uiso 1 1 calc R U . . .
C6A C -0.0516(8) 0.2155(7) 0.0343(3) 0.038(2) Uani 1 1 d . . . . .
H6A H 0.0304 0.2357 0.0333 0.046 Uiso 1 1 calc R U . . .
N7A N -0.2195(6) 0.1278(5) 0.1237(3) 0.0296(15) Uani 1 1 d . . . . .
C71A C -0.3404(9) 0.0953(9) 0.1300(5) 0.069(4) Uani 1 1 d . . . . .
H71A H -0.3320 0.0346 0.1434 0.104 Uiso 1 1 calc R U . . .
H71B H -0.3969 0.0950 0.0978 0.104 Uiso 1 1 calc R U . . .
H71C H -0.3743 0.1341 0.1531 0.104 Uiso 1 1 calc R U . . .
N8A N -0.1218(5) 0.1287(4) 0.1632(2) 0.0214(13) Uani 1 1 d . . . . .
C9A C -0.1396(7) 0.1038(5) 0.2062(3) 0.0261(16) Uani 1 1 d . . . . .
H9A H -0.2187 0.0845 0.2119 0.031 Uiso 1 1 calc R U . . .
C10A C -0.0306(7) 0.1071(5) 0.2455(3) 0.0211(15) Uani 1 1 d . . . . .
N11A N -0.0271(6) 0.0842(4) 0.2927(3) 0.0261(14) Uani 1 1 d . . . . .
C11A C -0.1332(8) 0.0546(6) 0.3145(4) 0.040(2) Uani 1 1 d . . . . .
H11A H -0.1961 0.1018 0.3112 0.060 Uiso 1 1 calc R U . . .
H11B H -0.1049 0.0409 0.3498 0.060 Uiso 1 1 calc R U . . .
H11C H -0.1697 0.0011 0.2972 0.060 Uiso 1 1 calc R U . . .
C12A C 0.0947(8) 0.0984(5) 0.3173(3) 0.0281(17) Uani 1 1 d . . . . .
H12A H 0.1263 0.0895 0.3517 0.034 Uiso 1 1 calc R U . . .
C13A C 0.1586(7) 0.1275(5) 0.2824(3) 0.0209(14) Uani 1 1 d . . . . .
H13A H 0.2450 0.1416 0.2883 0.025 Uiso 1 1 calc R U . . .
N14A N 0.0813(5) 0.1337(4) 0.2375(2) 0.0189(12) Uani 1 1 d . . . . .
N1B N 0.2799(6) 0.2561(4) 0.2043(2) 0.0205(12) Uani 1 1 d . . . . .
C2B C 0.3889(6) 0.2150(5) 0.2221(3) 0.0179(14) Uani 1 1 d . . . . .
C3B C 0.4947(7) 0.2599(5) 0.2472(3) 0.0276(17) Uani 1 1 d . . . . .
H3B H 0.5703 0.2289 0.2586 0.033 Uiso 1 1 calc R U . . .
C4B C 0.4858(8) 0.3499(5) 0.2548(3) 0.0293(18) Uani 1 1 d . . . . .
H4B H 0.5559 0.3823 0.2713 0.035 Uiso 1 1 calc R U . . .
C5B C 0.3722(7) 0.3936(5) 0.2377(3) 0.0242(16) Uani 1 1 d . . . . .
H5B H 0.3632 0.4555 0.2431 0.029 Uiso 1 1 calc R U . . .
C6B C 0.2759(7) 0.3444(5) 0.2135(3) 0.0226(15) Uani 1 1 d . . . . .
H6B H 0.1995 0.3744 0.2020 0.027 Uiso 1 1 calc R U . . .
N7B N 0.3935(5) 0.1238(4) 0.2146(2) 0.0210(13) Uani 1 1 d . . . . .
C71B C 0.4953(7) 0.0668(5) 0.2374(3) 0.0304(18) Uani 1 1 d . . . . .
H71D H 0.4632 0.0203 0.2569 0.046 Uiso 1 1 calc R U . . .
H71E H 0.5575 0.1025 0.2594 0.046 Uiso 1 1 calc R U . . .
H71F H 0.5340 0.0392 0.2115 0.046 Uiso 1 1 calc R U . . .
N8B N 0.2881(5) 0.0860(4) 0.1887(2) 0.0185(12) Uani 1 1 d . . . . .
C9B C 0.2854(7) 0.0020(5) 0.1805(3) 0.0217(15) Uani 1 1 d . . . . .
H9B H 0.3549 -0.0355 0.1917 0.026 Uiso 1 1 calc R U . . .
C10B C 0.1698(7) -0.0319(5) 0.1530(3) 0.0231(15) Uani 1 1 d . . . . .
N11B N 0.1443(6) -0.1174(4) 0.1405(3) 0.0287(15) Uani 1 1 d . . . . .
C11B C 0.2342(8) -0.1929(5) 0.1494(4) 0.034(2) Uani 1 1 d . . . . .
H11D H 0.3012 -0.1834 0.1305 0.050 Uiso 1 1 calc R U . . .
H11E H 0.1908 -0.2486 0.1388 0.050 Uiso 1 1 calc R U . . .
H11F H 0.2696 -0.1962 0.1849 0.050 Uiso 1 1 calc R U . . .
C12B C 0.0237(7) -0.1252(5) 0.1173(3) 0.0290(17) Uani 1 1 d . . . . .
H12B H -0.0192 -0.1777 0.1046 0.035 Uiso 1 1 calc R U . . .
C13B C -0.0222(7) -0.0401(6) 0.1165(3) 0.0314(19) Uani 1 1 d . . . . .
H13B H -0.1056 -0.0239 0.1029 0.038 Uiso 1 1 calc R U . . .
N14B N 0.0692(6) 0.0190(4) 0.1380(3) 0.0241(13) Uani 1 1 d . . . . .
S1C S 0.31463(19) 0.11560(16) 0.06761(8) 0.0327(5) Uani 1 1 d . . . . .
O11C O 0.4074(6) 0.1775(5) 0.0616(3) 0.0521(19) Uani 1 1 d . . . . .
O12C O 0.3569(7) 0.0285(5) 0.0851(3) 0.052(2) Uani 1 1 d . . . . .
O13C O 0.2120(5) 0.1518(4) 0.0897(2) 0.0260(12) Uani 1 1 d . . . . .
C1C C 0.2313(10) 0.0929(8) 0.0037(4) 0.047(3) Uani 1 1 d . . . . .
F11C F 0.1389(7) 0.0367(6) 0.0038(3) 0.078(2) Uani 1 1 d . . . . .
F12C F 0.1908(6) 0.1710(5) -0.0175(2) 0.0604(19) Uani 1 1 d . . . . .
F13C F 0.3115(7) 0.0574(6) -0.0228(2) 0.072(2) Uani 1 1 d . . . . .
O1D O -0.0113(5) 0.2978(3) 0.1841(2) 0.0228(11) Uani 1 1 d . . . . .
H1D H -0.0036 0.2974 0.2152 0.034 Uiso 1 1 d R U . . .
C1D C -0.1312(10) 0.3401(7) 0.1621(5) 0.052(3) Uani 1 1 d . . . . .
H1D1 H -0.1417 0.3383 0.1258 0.078 Uiso 1 1 calc R U . . .
H1D2 H -0.1314 0.4021 0.1732 0.078 Uiso 1 1 calc R U . . .
H1D3 H -0.2000 0.3079 0.1728 0.078 Uiso 1 1 calc R U . . .
O1E O 0.1237(6) 0.3194(4) 0.1110(2) 0.0303(12) Uani 1 1 d . . . . .
H1E H 0.0966 0.3605 0.1270 0.045 Uiso 1 1 d R U . . .
C1E C 0.2210(10) 0.3539(7) 0.0867(4) 0.044(2) Uani 1 1 d . . . . .
H1E1 H 0.2093 0.3313 0.0526 0.067 Uiso 1 1 calc R U . . .
H1E2 H 0.3024 0.3347 0.1049 0.067 Uiso 1 1 calc R U . . .
H1E3 H 0.2172 0.4191 0.0861 0.067 Uiso 1 1 calc R U . . .
S1F S 0.4527(4) 0.07136(19) 0.37547(11) 0.0639(9) Uani 1 1 d . . . . .
O11F O 0.3521(8) 0.0926(6) 0.4073(5) 0.087(3) Uani 1 1 d . . . . .
O12F O 0.4696(7) 0.1419(5) 0.3443(3) 0.0521(18) Uani 1 1 d . . . . .
O13F O 0.4400(5) -0.0124(4) 0.3545(2) 0.0319(13) Uani 1 1 d . U . . .
C1F C 0.5830(15) 0.0707(11) 0.4231(6) 0.082(4) Uani 1 1 d . . . . .
F11F F 0.6826(8) 0.0517(7) 0.3964(5) 0.118(4) Uani 1 1 d . . . . .
F12F F 0.5999(9) 0.1457(7) 0.4487(3) 0.103(3) Uani 1 1 d . . . . .
F13F F 0.5766(10) 0.0051(7) 0.4569(3) 0.106(3) Uani 1 1 d . . . . .
S1G S 0.85902(17) 0.33642(12) 0.29231(8) 0.0243(4) Uani 1 1 d . . . . .
O11G O 0.7909(5) 0.2588(4) 0.2726(2) 0.0324(13) Uani 1 1 d . . . . .
O12G O 0.9843(5) 0.3418(4) 0.2806(2) 0.0271(12) Uani 1 1 d . . . . .
O13G O 0.7906(5) 0.4190(4) 0.2863(2) 0.0312(13) Uani 1 1 d . . . . .
C1G C 0.8903(8) 0.3192(6) 0.3593(4) 0.037(2) Uani 1 1 d . . . . .
F11G F 0.9520(5) 0.2426(4) 0.3713(2) 0.0454(13) Uani 1 1 d . . . . .
F12G F 0.7828(6) 0.3131(5) 0.3769(2) 0.0548(16) Uani 1 1 d . . . . .
F13G F 0.9567(5) 0.3836(4) 0.3833(2) 0.0451(13) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Er1 O13C 2.332(5) . ?
Er1 O1D 2.391(5) . ?
Er1 O1E 2.435(6) . ?
Er1 N14B 2.446(6) . ?
Er1 N14A 2.464(6) . ?
Er1 N1B 2.514(6) . ?
Er1 N1A 2.521(7) . ?
Er1 N8B 2.557(6) . ?
Er1 N8A 2.572(6) . ?
N1A C6A 1.350(12) . ?
N1A C2A 1.355(11) . ?
C2A N7A 1.372(12) . ?
C2A C3A 1.404(12) . ?
C3A C4A 1.369(17) . ?
C3A H3A 0.9500 . ?
C4A C5A 1.384(17) . ?
C4A H4A 0.9500 . ?
C5A C6A 1.366(13) . ?
C5A H5A 0.9500 . ?
C6A H6A 0.9500 . ?
N7A N8A 1.376(9) . ?
N7A C71A 1.445(11) . ?
C71A H71A 0.9800 . ?
C71A H71B 0.9800 . ?
C71A H71C 0.9800 . ?
N8A C9A 1.280(10) . ?
C9A C10A 1.454(11) . ?
C9A H9A 0.9500 . ?
C10A N11A 1.330(10) . ?
C10A N14A 1.338(9) . ?
N11A C12A 1.394(10) . ?
N11A C11A 1.465(10) . ?
C11A H11A 0.9800 . ?
C11A H11B 0.9800 . ?
C11A H11C 0.9800 . ?
C12A C13A 1.353(11) . ?
C12A H12A 0.9500 . ?
C13A N14A 1.363(9) . ?
C13A H13A 0.9500 . ?
N1B C2B 1.351(9) . ?
N1B C6B 1.353(9) . ?
C2B N7B 1.388(9) . ?
C2B C3B 1.404(10) . ?
C3B C4B 1.373(11) . ?
C3B H3B 0.9500 . ?
C4B C5B 1.406(11) . ?
C4B H4B 0.9500 . ?
C5B C6B 1.355(10) . ?
C5B H5B 0.9500 . ?
C6B H6B 0.9500 . ?
N7B N8B 1.360(8) . ?
N7B C71B 1.452(9) . ?
C71B H71D 0.9800 . ?
C71B H71E 0.9800 . ?
C71B H71F 0.9800 . ?
N8B C9B 1.282(9) . ?
C9B C10B 1.440(10) . ?
C9B H9B 0.9500 . ?
C10B N14B 1.339(10) . ?
C10B N11B 1.345(10) . ?
N11B C12B 1.358(10) . ?
N11B C11B 1.490(10) . ?
C11B H11D 0.9800 . ?
C11B H11E 0.9800 . ?
C11B H11F 0.9800 . ?
C12B C13B 1.371(11) . ?
C12B H12B 0.9500 . ?
C13B N14B 1.384(9) . ?
C13B H13B 0.9500 . ?
S1C O11C 1.405(8) . ?
S1C O12C 1.441(7) . ?
S1C O13C 1.468(5) . ?
S1C C1C 1.852(11) . ?
C1C F11C 1.315(14) . ?
C1C F12C 1.347(12) . ?
C1C F13C 1.341(11) . ?
O1D C1D 1.481(12) . ?
O1D H1D 0.8400 . ?
C1D H1D1 0.9800 . ?
C1D H1D2 0.9800 . ?
C1D H1D3 0.9800 . ?
O1E C1E 1.446(11) . ?
O1E H1E 0.8400 . ?
C1E H1E1 0.9800 . ?
C1E H1E2 0.9800 . ?
C1E H1E3 0.9800 . ?
S1F O13F 1.380(6) . ?
S1F O12F 1.393(8) . ?
S1F O11F 1.553(10) . ?
S1F C1F 1.747(15) . ?
C1F F12F 1.322(17) . ?
C1F F13F 1.361(18) . ?
C1F F11F 1.443(19) . ?
S1G O11G 1.434(6) . ?
S1G O13G 1.442(6) . ?
S1G O12G 1.460(5) . ?
S1G C1G 1.821(10) . ?
C1G F13G 1.312(11) . ?
C1G F11G 1.343(10) . ?
C1G F12G 1.349(10) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O13C Er1 O1D 139.89(19) . . ?
O13C Er1 O1E 71.77(19) . . ?
O1D Er1 O1E 68.27(18) . . ?
O13C Er1 N14B 77.2(2) . . ?
O1D Er1 N14B 137.44(19) . . ?
O1E Er1 N14B 143.1(2) . . ?
O13C Er1 N14A 141.66(19) . . ?
O1D Er1 N14A 74.79(19) . . ?
O1E Er1 N14A 135.41(19) . . ?
N14B Er1 N14A 81.5(2) . . ?
O13C Er1 N1B 91.2(2) . . ?
O1D Er1 N1B 80.98(19) . . ?
O1E Er1 N1B 73.4(2) . . ?
N14B Er1 N1B 127.3(2) . . ?
N14A Er1 N1B 76.97(19) . . ?
O13C Er1 N1A 80.6(2) . . ?
O1D Er1 N1A 85.6(2) . . ?
O1E Er1 N1A 74.5(2) . . ?
N14B Er1 N1A 81.3(2) . . ?
N14A Er1 N1A 127.2(2) . . ?
N1B Er1 N1A 147.8(2) . . ?
O13C Er1 N8B 71.51(19) . . ?
O1D Er1 N8B 133.42(19) . . ?
O1E Er1 N8B 119.84(19) . . ?
N14B Er1 N8B 66.1(2) . . ?
N14A Er1 N8B 70.80(19) . . ?
N1B Er1 N8B 61.54(19) . . ?
N1A Er1 N8B 140.6(2) . . ?
O13C Er1 N8A 131.8(2) . . ?
O1D Er1 N8A 69.29(18) . . ?
O1E Er1 N8A 119.92(19) . . ?
N14B Er1 N8A 68.8(2) . . ?
N14A Er1 N8A 65.4(2) . . ?
N1B Er1 N8A 136.6(2) . . ?
N1A Er1 N8A 61.7(2) . . ?
N8B Er1 N8A 120.15(19) . . ?
C6A N1A C2A 117.9(7) . . ?
C6A N1A Er1 118.9(5) . . ?
C2A N1A Er1 123.1(6) . . ?
N1A C2A N7A 117.6(7) . . ?
N1A C2A C3A 121.6(9) . . ?
N7A C2A C3A 120.7(8) . . ?
C4A C3A C2A 118.2(9) . . ?
C4A C3A H3A 120.9 . . ?
C2A C3A H3A 120.9 . . ?
C3A C4A C5A 120.7(9) . . ?
C3A C4A H4A 119.6 . . ?
C5A C4A H4A 119.6 . . ?
C6A C5A C4A 118.0(11) . . ?
C6A C5A H5A 121.0 . . ?
C4A C5A H5A 121.0 . . ?
N1A C6A C5A 123.6(9) . . ?
N1A C6A H6A 118.2 . . ?
C5A C6A H6A 118.2 . . ?
C2A N7A N8A 116.5(6) . . ?
C2A N7A C71A 123.3(7) . . ?
N8A N7A C71A 120.2(7) . . ?
N7A C71A H71A 109.5 . . ?
N7A C71A H71B 109.5 . . ?
H71A C71A H71B 109.5 . . ?
N7A C71A H71C 109.5 . . ?
H71A C71A H71C 109.5 . . ?
H71B C71A H71C 109.5 . . ?
C9A N8A N7A 119.7(6) . . ?
C9A N8A Er1 119.3(5) . . ?
N7A N8A Er1 121.0(5) . . ?
N8A C9A C10A 115.5(6) . . ?
N8A C9A H9A 122.3 . . ?
C10A C9A H9A 122.3 . . ?
N11A C10A N14A 111.6(7) . . ?
N11A C10A C9A 125.9(7) . . ?
N14A C10A C9A 122.5(7) . . ?
C10A N11A C12A 106.8(6) . . ?
C10A N11A C11A 126.0(7) . . ?
C12A N11A C11A 127.1(7) . . ?
N11A C11A H11A 109.5 . . ?
N11A C11A H11B 109.5 . . ?
H11A C11A H11B 109.5 . . ?
N11A C11A H11C 109.5 . . ?
H11A C11A H11C 109.5 . . ?
H11B C11A H11C 109.5 . . ?
C13A C12A N11A 105.9(7) . . ?
C13A C12A H12A 127.0 . . ?
N11A C12A H12A 127.0 . . ?
C12A C13A N14A 110.2(7) . . ?
C12A C13A H13A 124.9 . . ?
N14A C13A H13A 124.9 . . ?
C10A N14A C13A 105.5(6) . . ?
C10A N14A Er1 117.2(5) . . ?
C13A N14A Er1 137.3(5) . . ?
C2B N1B C6B 115.8(6) . . ?
C2B N1B Er1 123.5(5) . . ?
C6B N1B Er1 120.6(5) . . ?
N1B C2B N7B 116.7(6) . . ?
N1B C2B C3B 123.3(7) . . ?
N7B C2B C3B 120.0(6) . . ?
C4B C3B C2B 118.2(7) . . ?
C4B C3B H3B 120.9 . . ?
C2B C3B H3B 120.9 . . ?
C3B C4B C5B 119.4(7) . . ?
C3B C4B H4B 120.3 . . ?
C5B C4B H4B 120.3 . . ?
C6B C5B C4B 117.8(7) . . ?
C6B C5B H5B 121.1 . . ?
C4B C5B H5B 121.1 . . ?
N1B C6B C5B 125.3(7) . . ?
N1B C6B H6B 117.3 . . ?
C5B C6B H6B 117.3 . . ?
N8B N7B C2B 116.1(6) . . ?
N8B N7B C71B 119.2(6) . . ?
C2B N7B C71B 124.2(6) . . ?
N7B C71B H71D 109.5 . . ?
N7B C71B H71E 109.5 . . ?
H71D C71B H71E 109.5 . . ?
N7B C71B H71F 109.5 . . ?
H71D C71B H71F 109.5 . . ?
H71E C71B H71F 109.5 . . ?
C9B N8B N7B 119.6(6) . . ?
C9B N8B Er1 118.5(5) . . ?
N7B N8B Er1 121.8(4) . . ?
N8B C9B C10B 115.5(7) . . ?
N8B C9B H9B 122.2 . . ?
C10B C9B H9B 122.2 . . ?
N14B C10B N11B 110.3(6) . . ?
N14B C10B C9B 123.4(7) . . ?
N11B C10B C9B 126.3(7) . . ?
C10B N11B C12B 109.8(6) . . ?
C10B N11B C11B 125.8(7) . . ?
C12B N11B C11B 124.4(6) . . ?
N11B C11B H11D 109.5 . . ?
N11B C11B H11E 109.5 . . ?
H11D C11B H11E 109.5 . . ?
N11B C11B H11F 109.5 . . ?
H11D C11B H11F 109.5 . . ?
H11E C11B H11F 109.5 . . ?
N11B C12B C13B 104.3(6) . . ?
N11B C12B H12B 127.8 . . ?
C13B C12B H12B 127.8 . . ?
C12B C13B N14B 111.0(6) . . ?
C12B C13B H13B 124.5 . . ?
N14B C13B H13B 124.5 . . ?
C10B N14B C13B 104.5(6) . . ?
C10B N14B Er1 116.1(5) . . ?
C13B N14B Er1 139.3(5) . . ?
O11C S1C O12C 116.5(5) . . ?
O11C S1C O13C 114.9(4) . . ?
O12C S1C O13C 115.0(4) . . ?
O11C S1C C1C 104.7(5) . . ?
O12C S1C C1C 102.7(5) . . ?
O13C S1C C1C 100.1(4) . . ?
S1C O13C Er1 156.4(3) . . ?
F11C C1C F12C 111.6(9) . . ?
F11C C1C F13C 108.7(10) . . ?
F12C C1C F13C 108.1(8) . . ?
F11C C1C S1C 111.2(7) . . ?
F12C C1C S1C 108.2(8) . . ?
F13C C1C S1C 109.0(7) . . ?
C1D O1D Er1 129.1(6) . . ?
C1D O1D H1D 109.6 . . ?
Er1 O1D H1D 113.4 . . ?
O1D C1D H1D1 109.5 . . ?
O1D C1D H1D2 109.5 . . ?
H1D1 C1D H1D2 109.5 . . ?
O1D C1D H1D3 109.5 . . ?
H1D1 C1D H1D3 109.5 . . ?
H1D2 C1D H1D3 109.5 . . ?
C1E O1E Er1 133.0(5) . . ?
C1E O1E H1E 109.4 . . ?
Er1 O1E H1E 108.3 . . ?
O1E C1E H1E1 109.5 . . ?
O1E C1E H1E2 109.5 . . ?
H1E1 C1E H1E2 109.5 . . ?
O1E C1E H1E3 109.5 . . ?
H1E1 C1E H1E3 109.5 . . ?
H1E2 C1E H1E3 109.5 . . ?
O13F S1F O12F 117.0(5) . . ?
O13F S1F O11F 113.1(5) . . ?
O12F S1F O11F 111.8(5) . . ?
O13F S1F C1F 108.2(6) . . ?
O12F S1F C1F 106.4(7) . . ?
O11F S1F C1F 98.3(8) . . ?
F12F C1F F13F 106.1(13) . . ?
F12F C1F F11F 113.0(13) . . ?
F13F C1F F11F 109.6(14) . . ?
F12F C1F S1F 114.0(12) . . ?
F13F C1F S1F 112.1(11) . . ?
F11F C1F S1F 102.0(10) . . ?
O11G S1G O13G 115.7(3) . . ?
O11G S1G O12G 113.9(3) . . ?
O13G S1G O12G 114.4(3) . . ?
O11G S1G C1G 104.6(4) . . ?
O13G S1G C1G 103.7(4) . . ?
O12G S1G C1G 102.4(4) . . ?
F13G C1G F11G 107.6(7) . . ?
F13G C1G F12G 107.9(7) . . ?
F11G C1G F12G 106.4(8) . . ?
F13G C1G S1G 112.7(7) . . ?
F11G C1G S1G 111.3(6) . . ?
F12G C1G S1G 110.6(6) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6A N1A C2A N7A -178.6(8) . . . . ?
Er1 N1A C2A N7A 1.2(11) . . . . ?
C6A N1A C2A C3A 1.4(13) . . . . ?
Er1 N1A C2A C3A -178.8(8) . . . . ?
N1A C2A C3A C4A -0.6(17) . . . . ?
N7A C2A C3A C4A 179.4(12) . . . . ?
C2A C3A C4A C5A 0(2) . . . . ?
C3A C4A C5A C6A 0(2) . . . . ?
C2A N1A C6A C5A -1.6(16) . . . . ?
Er1 N1A C6A C5A 178.6(10) . . . . ?
C4A C5A C6A N1A 1(2) . . . . ?
N1A C2A N7A N8A 0.5(11) . . . . ?
C3A C2A N7A N8A -179.5(9) . . . . ?
N1A C2A N7A C71A -178.4(10) . . . . ?
C3A C2A N7A C71A 1.6(15) . . . . ?
C2A N7A N8A C9A 178.4(7) . . . . ?
C71A N7A N8A C9A -2.7(12) . . . . ?
C2A N7A N8A Er1 -2.0(9) . . . . ?
C71A N7A N8A Er1 176.9(8) . . . . ?
N7A N8A C9A C10A 180.0(6) . . . . ?
Er1 N8A C9A C10A 0.3(9) . . . . ?
N8A C9A C10A N11A -179.7(7) . . . . ?
N8A C9A C10A N14A -0.5(10) . . . . ?
N14A C10A N11A C12A 1.3(8) . . . . ?
C9A C10A N11A C12A -179.5(7) . . . . ?
N14A C10A N11A C11A 178.1(7) . . . . ?
C9A C10A N11A C11A -2.7(12) . . . . ?
C10A N11A C12A C13A -1.6(8) . . . . ?
C11A N11A C12A C13A -178.3(7) . . . . ?
N11A C12A C13A N14A 1.3(8) . . . . ?
N11A C10A N14A C13A -0.5(8) . . . . ?
C9A C10A N14A C13A -179.7(7) . . . . ?
N11A C10A N14A Er1 179.7(5) . . . . ?
C9A C10A N14A Er1 0.4(9) . . . . ?
C12A C13A N14A C10A -0.6(8) . . . . ?
C12A C13A N14A Er1 179.2(5) . . . . ?
C6B N1B C2B N7B 177.8(6) . . . . ?
Er1 N1B C2B N7B -6.0(9) . . . . ?
C6B N1B C2B C3B -2.3(11) . . . . ?
Er1 N1B C2B C3B 173.9(6) . . . . ?
N1B C2B C3B C4B 1.3(12) . . . . ?
N7B C2B C3B C4B -178.8(7) . . . . ?
C2B C3B C4B C5B 0.6(12) . . . . ?
C3B C4B C5B C6B -1.2(12) . . . . ?
C2B N1B C6B C5B 1.6(11) . . . . ?
Er1 N1B C6B C5B -174.7(6) . . . . ?
C4B C5B C6B N1B 0.1(12) . . . . ?
N1B C2B N7B N8B 1.8(9) . . . . ?
C3B C2B N7B N8B -178.1(7) . . . . ?
N1B C2B N7B C71B -170.2(7) . . . . ?
C3B C2B N7B C71B 9.9(11) . . . . ?
C2B N7B N8B C9B -179.7(7) . . . . ?
C71B N7B N8B C9B -7.3(10) . . . . ?
C2B N7B N8B Er1 3.1(8) . . . . ?
C71B N7B N8B Er1 175.5(5) . . . . ?
N7B N8B C9B C10B 179.8(6) . . . . ?
Er1 N8B C9B C10B -2.9(9) . . . . ?
N8B C9B C10B N14B -2.2(11) . . . . ?
N8B C9B C10B N11B -179.1(8) . . . . ?
N14B C10B N11B C12B -1.0(10) . . . . ?
C9B C10B N11B C12B 176.3(8) . . . . ?
N14B C10B N11B C11B 177.9(8) . . . . ?
C9B C10B N11B C11B -4.8(14) . . . . ?
C10B N11B C12B C13B 0.0(10) . . . . ?
C11B N11B C12B C13B -178.9(8) . . . . ?
N11B C12B C13B N14B 0.9(10) . . . . ?
N11B C10B N14B C13B 1.5(9) . . . . ?
C9B C10B N14B C13B -175.8(8) . . . . ?
N11B C10B N14B Er1 -176.4(5) . . . . ?
C9B C10B N14B Er1 6.2(10) . . . . ?
C12B C13B N14B C10B -1.5(10) . . . . ?
C12B C13B N14B Er1 175.6(6) . . . . ?
O11C S1C O13C Er1 -102.2(10) . . . . ?
O12C S1C O13C Er1 37.1(11) . . . . ?
C1C S1C O13C Er1 146.3(9) . . . . ?
O11C S1C C1C F11C -178.6(7) . . . . ?
O12C S1C C1C F11C 59.3(8) . . . . ?
O13C S1C C1C F11C -59.3(8) . . . . ?
O11C S1C C1C F12C -55.7(8) . . . . ?
O12C S1C C1C F12C -177.8(7) . . . . ?
O13C S1C C1C F12C 63.6(7) . . . . ?
O11C S1C C1C F13C 61.6(9) . . . . ?
O12C S1C C1C F13C -60.5(9) . . . . ?
O13C S1C C1C F13C -179.2(8) . . . . ?
O13F S1F C1F F12F -175.3(11) . . . . ?
O12F S1F C1F F12F 58.2(14) . . . . ?
O11F S1F C1F F12F -57.5(14) . . . . ?
O13F S1F C1F F13F -54.6(13) . . . . ?
O12F S1F C1F F13F 178.9(11) . . . . ?
O11F S1F C1F F13F 63.2(12) . . . . ?
O13F S1F C1F F11F 62.6(11) . . . . ?
O12F S1F C1F F11F -64.0(11) . . . . ?
O11F S1F C1F F11F -179.6(9) . . . . ?
O11G S1G C1G F13G 177.8(6) . . . . ?
O13G S1G C1G F13G -60.5(7) . . . . ?
O12G S1G C1G F13G 58.7(7) . . . . ?
O11G S1G C1G F11G 56.8(7) . . . . ?
O13G S1G C1G F11G 178.5(6) . . . . ?
O12G S1G C1G F11G -62.3(7) . . . . ?
O11G S1G C1G F12G -61.3(7) . . . . ?
O13G S1G C1G F12G 60.4(7) . . . . ?
O12G S1G C1G F12G 179.6(6) . . . . ?

_refine_diff_density_max         5.671
_refine_diff_density_min         -3.189
_refine_diff_density_rms         0.197

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_18
_database_code_depnum_ccdc_archive 'CCDC 1052300'
_audit_update_record             
;
2016-01-10 deposited with the CCDC.	2024-07-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C11 H15 N8 O10 Tb, C H4 O'
_chemical_formula_sum            'C12 H19 N8 O11 Tb'
_chemical_formula_weight         610.27

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Tb Tb -9.1472 9.1891 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.2400(4)
_cell_length_b                   10.5276(6)
_cell_length_c                   12.3755(6)
_cell_angle_alpha                98.043(4)
_cell_angle_beta                 96.749(4)
_cell_angle_gamma                100.129(5)
_cell_volume                     1035.23(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    3956
_cell_measurement_theta_min      3.6430
_cell_measurement_theta_max      75.5001

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.958
_exptl_crystal_F_000             600
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_absorpt_coefficient_mu    17.488
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.09682
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21t (release 14-08-2012 CrysAlis171 .NET)
(compiled Aug 14 2012,18:12:40)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     1.5418
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_source         'SuperNova (Cu) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'SuperNova, Single source at offset), Atlas'
_diffrn_detector_area_resol_mean 10.5357
_diffrn_measurement_method       ω-scan
_diffrn_reflns_number            7534
_diffrn_reflns_av_unetI/netI     0.0409
_diffrn_reflns_av_R_equivalents  0.0472
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.646
_diffrn_reflns_theta_max         75.728
_diffrn_reflns_theta_full        70.000
_diffrn_measured_fraction_theta_max 0.963
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.963
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.963
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             4161
_reflns_number_gt                4034
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlis Pro (Agilent Technologies (2011))'
_computing_cell_refinement       'CrysAlis Pro (Agilent Technologies (2011))'
_computing_data_reduction        'CrysAlis Pro (Agilent Technologies (2011))'
_computing_structure_solution    'SIR92 (Altomare et al., 1993)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Mercury (MacRae et al., 2009)'
_computing_publication_material  'SHELXL-2013 (Sheldrick, 2013)'



_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0958P)²+0.9318P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4161
_refine_ls_number_parameters     301
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0459
_refine_ls_R_factor_gt           0.0451
_refine_ls_wR_factor_ref         0.1313
_refine_ls_wR_factor_gt          0.1302
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_restrained_S_all      1.085
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Tb1 Tb 0.70409(3) 0.23082(2) 0.71121(2) 0.02537(13) Uani 1 1 d . . . . .
N1A N 0.9553(5) 0.3018(4) 0.6177(4) 0.0312(9) Uani 1 1 d . . . . .
C2A C 1.0349(6) 0.4263(5) 0.6349(4) 0.0296(9) Uani 1 1 d . . . . .
C3A C 1.1779(7) 0.4652(6) 0.5864(5) 0.0379(12) Uani 1 1 d . . . . .
H3A H 1.2312 0.5525 0.5978 0.045 Uiso 1 1 calc R U . . .
C4A C 1.2366(7) 0.3721(7) 0.5223(5) 0.0450(14) Uani 1 1 d . . . . .
H4A H 1.3290 0.3965 0.4879 0.054 Uiso 1 1 calc R U . . .
C5A C 1.1598(8) 0.2419(7) 0.5080(6) 0.0465(14) Uani 1 1 d . . . . .
H5A H 1.2012 0.1770 0.4671 0.056 Uiso 1 1 calc R U . . .
C6A C 1.0194(7) 0.2127(6) 0.5568(5) 0.0391(12) Uani 1 1 d . . . . .
H6A H 0.9655 0.1256 0.5470 0.047 Uiso 1 1 calc R U . . .
N7A N 0.9713(5) 0.5175(4) 0.7003(4) 0.0328(9) Uani 1 1 d . . . . .
C7A C 1.0517(8) 0.6556(5) 0.7289(5) 0.0425(13) Uani 1 1 d . . . . .
H7A3 H 1.0039 0.7041 0.6777 0.064 Uiso 1 1 calc R U . . .
H7A2 H 1.1689 0.6643 0.7257 0.064 Uiso 1 1 calc R U . . .
H7A1 H 1.0351 0.6889 0.8022 0.064 Uiso 1 1 calc R U . . .
N8A N 0.8211(5) 0.4737(4) 0.7317(4) 0.0297(8) Uani 1 1 d . . . . .
C9A C 0.7399(7) 0.5557(5) 0.7769(4) 0.0324(10) Uani 1 1 d . . . . .
H9A H 0.7812 0.6454 0.7908 0.039 Uiso 1 1 calc R U . . .
C10A C 0.5800(6) 0.4986(5) 0.8046(4) 0.0311(10) Uani 1 1 d . . . . .
N11A N 0.4789(6) 0.5652(5) 0.8594(4) 0.0355(9) Uani 1 1 d . . . . .
C11A C 0.5102(10) 0.7056(6) 0.8984(6) 0.0511(16) Uani 1 1 d . . . . .
H11C H 0.6245 0.7349 0.9314 0.077 Uiso 1 1 calc R U . . .
H11B H 0.4389 0.7243 0.9520 0.077 Uiso 1 1 calc R U . . .
H11A H 0.4879 0.7502 0.8373 0.077 Uiso 1 1 calc R U . . .
C12A C 0.3438(7) 0.4750(6) 0.8695(5) 0.0400(12) Uani 1 1 d . . . . .
H12A H 0.2526 0.4913 0.9030 0.048 Uiso 1 1 calc R U . . .
C13A C 0.3670(7) 0.3569(6) 0.8214(5) 0.0385(12) Uani 1 1 d . . . . .
H13A H 0.2936 0.2778 0.8169 0.046 Uiso 1 1 calc R U . . .
N14A N 0.5139(6) 0.3723(4) 0.7810(4) 0.0345(9) Uani 1 1 d . . . . .
N1B N 0.5962(6) 0.2229(5) 0.4733(4) 0.0400(11) Uani 1 1 d . . . . .
O11B O 0.5538(8) 0.2232(6) 0.3761(4) 0.0694(16) Uani 1 1 d . . . . .
O12B O 0.6387(6) 0.1233(4) 0.5080(4) 0.0419(9) Uani 1 1 d . . . . .
O13B O 0.6008(5) 0.3198(4) 0.5463(4) 0.0411(9) Uani 1 1 d . . . . .
N1C N 0.7670(8) -0.0181(5) 0.7714(5) 0.0487(13) Uani 1 1 d . . . . .
O11C O 0.8121(10) -0.1147(6) 0.7957(7) 0.088(2) Uani 1 1 d . . . . .
O12C O 0.6880(7) 0.0474(5) 0.8292(4) 0.0510(11) Uani 1 1 d . . . . .
O13C O 0.7987(7) 0.0233(4) 0.6825(5) 0.0570(12) Uani 1 1 d . . . . .
N1D N 0.9261(7) 0.3025(6) 0.9248(4) 0.0483(13) Uani 1 1 d . . . . .
O11D O 1.0201(9) 0.3283(10) 1.0097(5) 0.101(3) Uani 1 1 d . . . . .
O12D O 0.9708(5) 0.2553(5) 0.8368(4) 0.0506(11) Uani 1 1 d . . . . .
O13D O 0.7773(7) 0.3173(5) 0.9175(4) 0.0499(11) Uani 1 1 d . . . . .
O1E O 0.4319(5) 0.0943(4) 0.6679(4) 0.0441(9) Uani 1 1 d D . . . .
H1E H 0.371(12) 0.067(9) 0.720(8) 0.06(3) Uiso 1 1 d . . . . .
H2E H 0.414(13) 0.036(8) 0.605(5) 0.08(3) Uiso 1 1 d D . . . .
C1F C 0.2290(19) -0.0058(12) 0.9012(11) 0.105(4) Uani 1 1 d . . . . .
H1F3 H 0.3412 -0.0183 0.9185 0.158 Uiso 1 1 calc R U . . .
H1F2 H 0.1526 -0.0805 0.9138 0.158 Uiso 1 1 calc R U . . .
H1F1 H 0.2138 0.0711 0.9474 0.158 Uiso 1 1 calc R U . . .
O1F O 0.1994(10) 0.0088(13) 0.7920(8) 0.115(3) Uani 1 1 d . . . . .
H1F H 0.1107 0.0332 0.7802 0.173 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Tb1 O1E 2.398(4) . ?
Tb1 O13C 2.440(4) . ?
Tb1 O13B 2.484(4) . ?
Tb1 O12D 2.490(4) . ?
Tb1 N14A 2.490(5) . ?
Tb1 N8A 2.535(4) . ?
Tb1 N1A 2.538(4) . ?
Tb1 O13D 2.551(5) . ?
Tb1 O12B 2.563(4) . ?
Tb1 O12C 2.573(5) . ?
Tb1 N1C 2.937(5) . ?
Tb1 N1D 2.954(5) . ?
N1A C2A 1.335(7) . ?
N1A C6A 1.341(7) . ?
C2A N7A 1.382(7) . ?
C2A C3A 1.408(8) . ?
C3A C4A 1.365(9) . ?
C3A H3A 0.9300 . ?
C4A C5A 1.383(10) . ?
C4A H4A 0.9300 . ?
C5A C6A 1.374(9) . ?
C5A H5A 0.9300 . ?
C6A H6A 0.9300 . ?
N7A N8A 1.363(6) . ?
N7A C7A 1.463(7) . ?
C7A H7A3 0.9600 . ?
C7A H7A2 0.9600 . ?
C7A H7A1 0.9600 . ?
N8A C9A 1.290(7) . ?
C9A C10A 1.449(8) . ?
C9A H9A 0.9300 . ?
C10A N14A 1.323(7) . ?
C10A N11A 1.360(7) . ?
N11A C12A 1.361(8) . ?
N11A C11A 1.457(8) . ?
C11A H11C 0.9600 . ?
C11A H11B 0.9600 . ?
C11A H11A 0.9600 . ?
C12A C13A 1.356(8) . ?
C12A H12A 0.9300 . ?
C13A N14A 1.355(7) . ?
C13A H13A 0.9300 . ?
N1B O11B 1.214(7) . ?
N1B O13B 1.257(7) . ?
N1B O12B 1.274(7) . ?
N1C O11C 1.206(8) . ?
N1C O12C 1.241(8) . ?
N1C O13C 1.278(8) . ?
N1D O11D 1.197(8) . ?
N1D O12D 1.255(8) . ?
N1D O13D 1.258(8) . ?
O1E H1E 0.91(10) . ?
O1E H2E 0.899(10) . ?
C1F O1F 1.380(15) . ?
C1F H1F3 0.9600 . ?
C1F H1F2 0.9600 . ?
C1F H1F1 0.9600 . ?
O1F H1F 0.8200 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1E Tb1 O13C 83.76(17) . . ?
O1E Tb1 O13B 81.50(15) . . ?
O13C Tb1 O13B 118.20(16) . . ?
O1E Tb1 O12D 140.34(17) . . ?
O13C Tb1 O12D 72.33(19) . . ?
O13B Tb1 O12D 137.67(15) . . ?
O1E Tb1 N14A 75.27(15) . . ?
O13C Tb1 N14A 152.63(16) . . ?
O13B Tb1 N14A 76.26(15) . . ?
O12D Tb1 N14A 113.93(16) . . ?
O1E Tb1 N8A 135.68(15) . . ?
O13C Tb1 N8A 139.21(16) . . ?
O13B Tb1 N8A 69.22(13) . . ?
O12D Tb1 N8A 77.81(16) . . ?
N14A Tb1 N8A 66.12(15) . . ?
O1E Tb1 N1A 139.51(15) . . ?
O13C Tb1 N1A 81.06(15) . . ?
O13B Tb1 N1A 73.28(14) . . ?
O12D Tb1 N1A 68.06(14) . . ?
N14A Tb1 N1A 126.28(15) . . ?
N8A Tb1 N1A 62.09(14) . . ?
O1E Tb1 O13D 111.34(16) . . ?
O13C Tb1 O13D 105.88(18) . . ?
O13B Tb1 O13D 135.35(15) . . ?
O12D Tb1 O13D 49.91(16) . . ?
N14A Tb1 O13D 67.05(16) . . ?
N8A Tb1 O13D 73.12(15) . . ?
N1A Tb1 O13D 108.87(16) . . ?
O1E Tb1 O12B 67.88(15) . . ?
O13C Tb1 O12B 68.64(17) . . ?
O13B Tb1 O12B 50.19(14) . . ?
O12D Tb1 O12B 126.99(16) . . ?
N14A Tb1 O12B 117.35(16) . . ?
N8A Tb1 O12B 111.45(14) . . ?
N1A Tb1 O12B 71.64(14) . . ?
O13D Tb1 O12B 174.45(14) . . ?
O1E Tb1 O12C 70.90(17) . . ?
O13C Tb1 O12C 50.20(17) . . ?
O13B Tb1 O12C 150.61(15) . . ?
O12D Tb1 O12C 69.47(16) . . ?
N14A Tb1 O12C 105.30(16) . . ?
N8A Tb1 O12C 139.00(15) . . ?
N1A Tb1 O12C 122.67(15) . . ?
O13D Tb1 O12C 67.07(17) . . ?
O12B Tb1 O12C 107.84(15) . . ?
O1E Tb1 N1C 77.84(16) . . ?
O13C Tb1 N1C 25.40(17) . . ?
O13B Tb1 N1C 139.41(16) . . ?
O12D Tb1 N1C 66.91(17) . . ?
N14A Tb1 N1C 129.82(16) . . ?
N8A Tb1 N1C 144.69(15) . . ?
N1A Tb1 N1C 101.41(15) . . ?
O13D Tb1 N1C 84.96(17) . . ?
O12B Tb1 N1C 89.52(16) . . ?
O12C Tb1 N1C 24.93(16) . . ?
O1E Tb1 N1D 128.87(16) . . ?
O13C Tb1 N1D 89.07(19) . . ?
O13B Tb1 N1D 143.01(15) . . ?
O12D Tb1 N1D 24.84(16) . . ?
N14A Tb1 N1D 90.56(16) . . ?
N8A Tb1 N1D 73.83(15) . . ?
N1A Tb1 N1D 88.25(15) . . ?
O13D Tb1 N1D 25.07(16) . . ?
O12B Tb1 N1D 151.64(16) . . ?
O12C Tb1 N1D 66.04(16) . . ?
N1C Tb1 N1D 74.73(18) . . ?
C2A N1A C6A 118.2(5) . . ?
C2A N1A Tb1 121.2(3) . . ?
C6A N1A Tb1 120.4(4) . . ?
N1A C2A N7A 118.2(4) . . ?
N1A C2A C3A 121.4(5) . . ?
N7A C2A C3A 120.4(5) . . ?
C4A C3A C2A 118.6(5) . . ?
C4A C3A H3A 120.7 . . ?
C2A C3A H3A 120.7 . . ?
C3A C4A C5A 120.6(5) . . ?
C3A C4A H4A 119.7 . . ?
C5A C4A H4A 119.7 . . ?
C6A C5A C4A 117.0(6) . . ?
C6A C5A H5A 121.5 . . ?
C4A C5A H5A 121.5 . . ?
N1A C6A C5A 124.1(6) . . ?
N1A C6A H6A 117.9 . . ?
C5A C6A H6A 117.9 . . ?
N8A N7A C2A 116.1(4) . . ?
N8A N7A C7A 120.7(5) . . ?
C2A N7A C7A 123.1(5) . . ?
N7A C7A H7A3 109.5 . . ?
N7A C7A H7A2 109.5 . . ?
H7A3 C7A H7A2 109.5 . . ?
N7A C7A H7A1 109.5 . . ?
H7A3 C7A H7A1 109.5 . . ?
H7A2 C7A H7A1 109.5 . . ?
C9A N8A N7A 120.1(4) . . ?
C9A N8A Tb1 119.0(4) . . ?
N7A N8A Tb1 120.8(3) . . ?
N8A C9A C10A 115.4(5) . . ?
N8A C9A H9A 122.3 . . ?
C10A C9A H9A 122.3 . . ?
N14A C10A N11A 110.6(5) . . ?
N14A C10A C9A 123.8(5) . . ?
N11A C10A C9A 125.5(5) . . ?
C10A N11A C12A 106.4(5) . . ?
C10A N11A C11A 126.3(5) . . ?
C12A N11A C11A 127.3(5) . . ?
N11A C11A H11C 109.5 . . ?
N11A C11A H11B 109.5 . . ?
H11C C11A H11B 109.5 . . ?
N11A C11A H11A 109.5 . . ?
H11C C11A H11A 109.5 . . ?
H11B C11A H11A 109.5 . . ?
C13A C12A N11A 107.1(5) . . ?
C13A C12A H12A 126.4 . . ?
N11A C12A H12A 126.4 . . ?
N14A C13A C12A 109.3(5) . . ?
N14A C13A H13A 125.3 . . ?
C12A C13A H13A 125.3 . . ?
C10A N14A C13A 106.4(5) . . ?
C10A N14A Tb1 114.8(3) . . ?
C13A N14A Tb1 137.6(4) . . ?
O11B N1B O13B 122.5(6) . . ?
O11B N1B O12B 121.9(6) . . ?
O13B N1B O12B 115.6(5) . . ?
O11B N1B Tb1 178.2(4) . . ?
O13B N1B Tb1 56.0(3) . . ?
O12B N1B Tb1 59.6(3) . . ?
N1B O12B Tb1 94.9(3) . . ?
N1B O13B Tb1 99.3(3) . . ?
O11C N1C O12C 123.5(7) . . ?
O11C N1C O13C 121.1(7) . . ?
O12C N1C O13C 115.5(5) . . ?
O11C N1C Tb1 172.4(6) . . ?
O12C N1C Tb1 60.9(3) . . ?
O13C N1C Tb1 55.0(3) . . ?
N1C O12C Tb1 94.2(3) . . ?
N1C O13C Tb1 99.6(4) . . ?
O11D N1D O12D 121.1(7) . . ?
O11D N1D O13D 123.2(7) . . ?
O12D N1D O13D 115.7(5) . . ?
O11D N1D Tb1 177.4(7) . . ?
O12D N1D Tb1 56.4(3) . . ?
O13D N1D Tb1 59.2(3) . . ?
N1D O12D Tb1 98.7(3) . . ?
N1D O13D Tb1 95.7(3) . . ?
Tb1 O1E H1E 123(6) . . ?
Tb1 O1E H2E 116(7) . . ?
H1E O1E H2E 113(9) . . ?
O1F C1F H1F3 109.5 . . ?
O1F C1F H1F2 109.5 . . ?
H1F3 C1F H1F2 109.5 . . ?
O1F C1F H1F1 109.5 . . ?
H1F3 C1F H1F1 109.5 . . ?
H1F2 C1F H1F1 109.5 . . ?
C1F O1F H1F 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6A N1A C2A N7A -178.2(5) . . . . ?
Tb1 N1A C2A N7A -3.6(6) . . . . ?
C6A N1A C2A C3A 3.0(7) . . . . ?
Tb1 N1A C2A C3A 177.6(4) . . . . ?
N1A C2A C3A C4A -1.2(8) . . . . ?
N7A C2A C3A C4A -179.9(5) . . . . ?
C2A C3A C4A C5A -1.8(9) . . . . ?
C3A C4A C5A C6A 2.8(10) . . . . ?
C2A N1A C6A C5A -2.0(9) . . . . ?
Tb1 N1A C6A C5A -176.6(5) . . . . ?
C4A C5A C6A N1A -0.9(10) . . . . ?
N1A C2A N7A N8A -7.1(7) . . . . ?
C3A C2A N7A N8A 171.7(5) . . . . ?
N1A C2A N7A C7A 177.2(5) . . . . ?
C3A C2A N7A C7A -4.0(8) . . . . ?
C2A N7A N8A C9A -168.6(5) . . . . ?
C7A N7A N8A C9A 7.3(8) . . . . ?
C2A N7A N8A Tb1 14.6(6) . . . . ?
C7A N7A N8A Tb1 -169.6(4) . . . . ?
N7A N8A C9A C10A 178.6(4) . . . . ?
Tb1 N8A C9A C10A -4.4(6) . . . . ?
N8A C9A C10A N14A -3.5(8) . . . . ?
N8A C9A C10A N11A 175.2(5) . . . . ?
N14A C10A N11A C12A -0.2(6) . . . . ?
C9A C10A N11A C12A -179.1(5) . . . . ?
N14A C10A N11A C11A -179.8(6) . . . . ?
C9A C10A N11A C11A 1.3(9) . . . . ?
C10A N11A C12A C13A 0.4(6) . . . . ?
C11A N11A C12A C13A 179.9(6) . . . . ?
N11A C12A C13A N14A -0.4(7) . . . . ?
N11A C10A N14A C13A 0.0(6) . . . . ?
C9A C10A N14A C13A 178.9(5) . . . . ?
N11A C10A N14A Tb1 -169.5(3) . . . . ?
C9A C10A N14A Tb1 9.4(7) . . . . ?
C12A C13A N14A C10A 0.2(7) . . . . ?
C12A C13A N14A Tb1 166.1(4) . . . . ?
O11B N1B O12B Tb1 178.8(5) . . . . ?
O13B N1B O12B Tb1 -1.3(5) . . . . ?
O11B N1B O13B Tb1 -178.8(5) . . . . ?
O12B N1B O13B Tb1 1.4(5) . . . . ?
O11C N1C O12C Tb1 172.7(7) . . . . ?
O13C N1C O12C Tb1 -7.3(6) . . . . ?
O11C N1C O13C Tb1 -172.2(7) . . . . ?
O12C N1C O13C Tb1 7.8(6) . . . . ?
O11D N1D O12D Tb1 179.0(7) . . . . ?
O13D N1D O12D Tb1 0.5(6) . . . . ?
O11D N1D O13D Tb1 -178.9(8) . . . . ?
O12D N1D O13D Tb1 -0.5(6) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C3A H3A O11B 0.93 2.64 3.555(8) 166.4 2_766
C5A H5A O13C 0.93 2.60 3.486(8) 158.4 2_756
C6A H6A O13C 0.93 2.53 3.156(8) 125.1 .
C7A H7A1 O11D 0.96 2.45 3.342(10) 154.9 2_767
C9A H9A O11C 0.93 2.48 3.385(8) 163.2 1_565
C11A H11B O13D 0.96 2.56 3.476(9) 159.0 2_667
O1E H2E O12B 0.899(10) 1.98(3) 2.857(6) 166(9) 2_656
O1E H1E O1F 0.91(10) 1.82(10) 2.704(9) 163(9) .

_refine_diff_density_max         1.867
_refine_diff_density_min         -2.254
_refine_diff_density_rms         0.153

_shelxl_version_number           2013-4

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_07a
_database_code_depnum_ccdc_archive 'CCDC 1052306'
_audit_update_record             
;
2016-01-10 deposited with the CCDC.	2024-07-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H26 F6 N11 O6 S2 Tb, C F3 O3 S'
_chemical_formula_sum            'C27 H26 F9 N11 O9 S3 Tb'
_chemical_formula_weight         1074.69

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Tb Tb -9.1472 9.1891 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   19.0497(5)
_cell_length_b                   10.3198(2)
_cell_length_c                   21.3425(5)
_cell_angle_alpha                90
_cell_angle_beta                 102.668(2)
_cell_angle_gamma                90
_cell_volume                     4093.57(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    4075
_cell_measurement_theta_min      2.1060
_cell_measurement_theta_max      61.4290

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.744
_exptl_crystal_F_000             2124
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.1
_exptl_absorpt_coefficient_mu    10.863
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.28745
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     1.5418
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_source         'SuperNova (Cu) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'SuperNova, Single source at offset), Atlas'
_diffrn_detector_area_resol_mean 10.5357
_diffrn_measurement_method       ω-scan
_diffrn_reflns_number            16653
_diffrn_reflns_av_unetI/netI     0.0255
_diffrn_reflns_av_R_equivalents  0.0232
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.377
_diffrn_reflns_theta_max         67.499
_diffrn_reflns_theta_full        67.500
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             7381
_reflns_number_gt                6405
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlis Pro (Agilent Technologies (2011))'
_computing_cell_refinement       'CrysAlis Pro (Agilent Technologies (2011))'
_computing_data_reduction        'CrysAlis Pro (Agilent Technologies (2011))'
_computing_structure_solution    'SIR92 (Altomare et al., 1993)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Mercury (MacRae et al., 2009)'
_computing_publication_material  'SHELXL-2013 (Sheldrick, 2013)'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0980P)²+4.3701P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7381
_refine_ls_number_parameters     545
_refine_ls_number_restraints     223
_refine_ls_R_factor_all          0.0758
_refine_ls_R_factor_gt           0.0688
_refine_ls_wR_factor_ref         0.2111
_refine_ls_wR_factor_gt          0.2057
_refine_ls_goodness_of_fit_ref   1.446
_refine_ls_restrained_S_all      1.650
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Tb1 Tb 0.77349(2) 0.00875(4) 0.09297(2) 0.04674(18) Uani 1 1 d . . . . .
N1A N 0.8407(3) 0.1904(6) 0.0475(3) 0.0541(13) Uani 1 1 d . . . . .
C2A C 0.8221(4) 0.2283(7) -0.0124(3) 0.0539(15) Uani 1 1 d . . . . .
C3A C 0.8614(6) 0.3185(10) -0.0406(5) 0.091(3) Uani 1 1 d . . . . .
H3A H 0.8457 0.3458 -0.0829 0.109 Uiso 1 1 calc R U . . .
C4A C 0.9227(8) 0.3630(14) -0.0031(5) 0.127(6) Uani 1 1 d . . . . .
H4A H 0.9513 0.4204 -0.0200 0.152 Uiso 1 1 calc R U . . .
C5A C 0.9441(7) 0.3240(12) 0.0612(5) 0.108(4) Uani 1 1 d . . . . .
H5A H 0.9871 0.3532 0.0870 0.130 Uiso 1 1 calc R U . . .
C6A C 0.9005(4) 0.2429(9) 0.0845(4) 0.073(2) Uani 1 1 d . . . . .
H6A H 0.9121 0.2224 0.1280 0.087 Uiso 1 1 calc R U . . .
N7A N 0.7580(3) 0.1792(6) -0.0516(3) 0.0585(14) Uani 1 1 d . . . . .
C71A C 0.7368(5) 0.1994(12) -0.1201(4) 0.087(3) Uani 1 1 d . . . . .
H71A H 0.7276 0.1172 -0.1414 0.131 Uiso 1 1 calc R U . . .
H71B H 0.7747 0.2430 -0.1347 0.131 Uiso 1 1 calc R U . . .
H71C H 0.6940 0.2514 -0.1297 0.131 Uiso 1 1 calc R U . . .
N8A N 0.7204(3) 0.0990(6) -0.0201(3) 0.0510(12) Uani 1 1 d . . . . .
C9A C 0.6592(4) 0.0512(8) -0.0512(3) 0.0562(16) Uani 1 1 d . . . . .
H9A H 0.6393 0.0736 -0.0936 0.067 Uiso 1 1 calc R U . . .
C10A C 0.6247(4) -0.0370(7) -0.0164(4) 0.0554(16) Uani 1 1 d . . . . .
N11A N 0.5619(3) -0.0982(7) -0.0415(3) 0.0680(17) Uani 1 1 d . . . . .
C11A C 0.5190(5) -0.0874(11) -0.1071(5) 0.095(3) Uani 1 1 d . . . . .
H11A H 0.5058 -0.1724 -0.1239 0.142 Uiso 1 1 calc R U . . .
H11B H 0.5468 -0.0446 -0.1335 0.142 Uiso 1 1 calc R U . . .
H11C H 0.4763 -0.0380 -0.1070 0.142 Uiso 1 1 calc R U . . .
C12A C 0.5488(5) -0.1779(9) 0.0061(5) 0.082(3) Uani 1 1 d . . . . .
H12A H 0.5100 -0.2340 0.0030 0.098 Uiso 1 1 calc R U . . .
C13A C 0.6026(5) -0.1602(8) 0.0582(4) 0.072(2) Uani 1 1 d . . . . .
H13A H 0.6065 -0.2012 0.0976 0.086 Uiso 1 1 calc R U . . .
N14A N 0.6511(3) -0.0716(6) 0.0438(3) 0.0583(14) Uani 1 1 d . . . . .
N1B N 0.7789(3) -0.2029(6) 0.1550(3) 0.0613(15) Uani 1 1 d . . . . .
C2B C 0.7460(4) -0.2190(7) 0.2035(4) 0.0572(16) Uani 1 1 d . . . . .
C3B C 0.7548(5) -0.3335(8) 0.2410(4) 0.075(2) Uani 1 1 d . . . . .
H3B H 0.7313 -0.3440 0.2745 0.090 Uiso 1 1 calc R U . . .
C4B C 0.7987(6) -0.4281(9) 0.2263(5) 0.088(3) Uani 1 1 d . . . . .
H4B H 0.8072 -0.5022 0.2517 0.106 Uiso 1 1 calc R U . . .
C5B C 0.8307(5) -0.4157(8) 0.1750(5) 0.073(2) Uani 1 1 d . . . . .
H5B H 0.8582 -0.4821 0.1633 0.088 Uiso 1 1 calc R U . . .
C6B C 0.8200(5) -0.2999(8) 0.1412(4) 0.071(2) Uani 1 1 d . . . . .
H6B H 0.8427 -0.2887 0.1071 0.085 Uiso 1 1 calc R U . . .
N7B N 0.7016(4) -0.1213(6) 0.2161(3) 0.0656(16) Uani 1 1 d . . . . .
C71B C 0.6592(7) -0.1275(10) 0.2658(5) 0.093(3) Uani 1 1 d . . . . .
H71D H 0.6838 -0.0812 0.3032 0.140 Uiso 1 1 calc R U . . .
H71E H 0.6532 -0.2163 0.2768 0.140 Uiso 1 1 calc R U . . .
H71F H 0.6129 -0.0889 0.2498 0.140 Uiso 1 1 calc R U . . .
N8B N 0.7021(4) -0.0110(5) 0.1822(3) 0.0528(14) Uani 1 1 d . . . . .
C9B C 0.6675(4) 0.0886(7) 0.1949(3) 0.0553(16) Uani 1 1 d . . . . .
H9B H 0.6414 0.0874 0.2270 0.066 Uiso 1 1 calc R U . . .
C10B C 0.6713(4) 0.2014(7) 0.1573(3) 0.0520(15) Uani 1 1 d . . . . .
N11B N 0.6437(3) 0.3201(6) 0.1661(3) 0.0584(14) Uani 1 1 d . . . . .
C11B C 0.6104(6) 0.3572(10) 0.2184(4) 0.086(3) Uani 1 1 d . . . . .
H11D H 0.5791 0.2891 0.2262 0.130 Uiso 1 1 calc R U . . .
H11E H 0.5831 0.4352 0.2071 0.130 Uiso 1 1 calc R U . . .
H11F H 0.6471 0.3719 0.2564 0.130 Uiso 1 1 calc R U . . .
C12B C 0.6566(5) 0.3989(8) 0.1179(4) 0.0662(19) Uani 1 1 d . . . . .
H12B H 0.6434 0.4854 0.1110 0.079 Uiso 1 1 calc R U . . .
C13B C 0.6923(5) 0.3259(8) 0.0827(4) 0.0662(19) Uani 1 1 d . . . . .
H13B H 0.7083 0.3552 0.0471 0.079 Uiso 1 1 calc R U . . .
N14B N 0.7019(3) 0.2016(6) 0.1071(3) 0.0549(13) Uani 1 1 d . . . . .
S1C S 0.86089(12) 0.1446(2) 0.25497(10) 0.0768(6) Uani 1 1 d . U . . .
O11C O 0.8704(7) 0.2739(10) 0.2601(6) 0.175(4) Uani 1 1 d . U . . .
O12C O 0.8198(6) 0.0905(14) 0.2973(4) 0.151(4) Uani 1 1 d . U . . .
O13C O 0.8408(3) 0.0970(6) 0.1900(2) 0.0669(13) Uani 1 1 d . U . . .
C1C C 0.9456(8) 0.0825(18) 0.2870(6) 0.124(3) Uani 1 1 d . U . . .
F11C F 0.9914(5) 0.1137(15) 0.2513(5) 0.192(4) Uani 1 1 d . U . . .
F12C F 0.9503(8) -0.0381(12) 0.2807(5) 0.193(4) Uani 1 1 d . U . . .
F13C F 0.9735(5) 0.1120(11) 0.3456(3) 0.158(3) Uani 1 1 d . U . . .
N1D N 0.9069(4) -0.0548(8) 0.1098(4) 0.0748(18) Uani 1 1 d . . . . .
C2D C 0.9658(6) -0.0583(11) 0.1113(5) 0.087(3) Uani 1 1 d . . . . .
C3D C 1.0432(7) -0.0623(19) 0.1143(10) 0.154(7) Uani 1 1 d . . . . .
S1E S 0.8055(3) -0.1781(3) -0.04613(17) 0.1324(14) Uani 1 1 d D U . . .
O11E O 0.7902(3) -0.1402(5) 0.0131(2) 0.0716(14) Uani 1 1 d D U . . .
O12E O 0.8273(7) -0.0927(11) -0.0865(5) 0.180(4) Uani 1 1 d D U . . .
O13E O 0.7271(5) -0.2049(15) -0.0905(5) 0.207(5) Uani 1 1 d D U . . .
C1E C 0.8277(7) -0.3453(9) -0.0428(6) 0.193(5) Uani 1 1 d D U . . .
F11E F 0.8196(9) -0.3806(13) -0.1042(6) 0.256(6) Uani 1 1 d D U . . .
F12E F 0.7730(7) -0.4032(12) -0.0220(6) 0.219(5) Uani 1 1 d D U . . .
F13E F 0.8932(6) -0.3276(14) -0.0073(6) 0.233(5) Uani 1 1 d D U . . .
S1F S 0.51605(11) 0.3459(2) 0.83463(11) 0.0700(5) Uani 1 1 d . . . . .
O11F O 0.4415(3) 0.3564(6) 0.8366(4) 0.0890(19) Uani 1 1 d . . . . .
O12F O 0.5460(4) 0.2218(7) 0.8543(5) 0.112(3) Uani 1 1 d . . . . .
O13F O 0.5348(5) 0.3996(8) 0.7790(3) 0.103(2) Uani 1 1 d . . . . .
C1F C 0.5595(7) 0.4546(13) 0.8984(6) 0.098(3) Uani 1 1 d . . . . .
F11F F 0.6307(5) 0.4524(10) 0.9058(5) 0.151(3) Uani 1 1 d . . . . .
F12F F 0.5485(8) 0.4216(13) 0.9532(4) 0.191(5) Uani 1 1 d . . . . .
F13F F 0.5404(6) 0.5747(8) 0.8866(5) 0.155(3) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Tb1 O13C 2.365(5) . ?
Tb1 O11E 2.367(5) . ?
Tb1 N14B 2.469(6) . ?
Tb1 N14A 2.481(6) . ?
Tb1 N1B 2.544(7) . ?
Tb1 N1D 2.572(7) . ?
Tb1 N1A 2.576(6) . ?
Tb1 N8A 2.576(5) . ?
Tb1 N8B 2.580(6) . ?
N1A C2A 1.308(9) . ?
N1A C6A 1.350(10) . ?
C2A C3A 1.409(11) . ?
C2A N7A 1.414(9) . ?
C3A C4A 1.344(15) . ?
C4A C5A 1.402(16) . ?
C5A C6A 1.349(13) . ?
N7A N8A 1.365(8) . ?
N7A C71A 1.443(10) . ?
N8A C9A 1.306(9) . ?
C9A C10A 1.423(11) . ?
C10A N14A 1.322(10) . ?
C10A N11A 1.355(9) . ?
N11A C12A 1.372(12) . ?
N11A C11A 1.462(11) . ?
C12A C13A 1.349(13) . ?
C13A N14A 1.381(10) . ?
N1B C2B 1.333(9) . ?
N1B C6B 1.343(10) . ?
C2B N7B 1.380(10) . ?
C2B C3B 1.416(11) . ?
C3B C4B 1.366(13) . ?
C4B C5B 1.371(14) . ?
C5B C6B 1.388(12) . ?
N7B N8B 1.349(8) . ?
N7B C71B 1.468(10) . ?
N8B C9B 1.282(9) . ?
C9B C10B 1.425(10) . ?
C10B N14B 1.326(9) . ?
C10B N11B 1.362(9) . ?
N11B C12B 1.376(10) . ?
N11B C11B 1.449(9) . ?
C12B C13B 1.348(11) . ?
C13B N14B 1.381(10) . ?
S1C O11C 1.347(11) . ?
S1C O12C 1.432(10) . ?
S1C O13C 1.442(5) . ?
S1C C1C 1.732(12) . ?
C1C F12C 1.26(2) . ?
C1C F13C 1.284(13) . ?
C1C F11C 1.316(19) . ?
N1D C2D 1.117(12) . ?
C2D C3D 1.461(16) . ?
S1E O12E 1.360(7) . ?
S1E O11E 1.415(5) . ?
S1E O13E 1.608(8) . ?
S1E C1E 1.774(8) . ?
C1E F13E 1.322(9) . ?
C1E F11E 1.337(9) . ?
C1E F12E 1.358(9) . ?
S1F O13F 1.424(7) . ?
S1F O12F 1.427(7) . ?
S1F O11F 1.433(6) . ?
S1F C1F 1.817(14) . ?
C1F F12F 1.277(14) . ?
C1F F13F 1.301(16) . ?
C1F F11F 1.331(15) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O13C Tb1 O11E 138.4(2) . . ?
O13C Tb1 N14B 77.9(2) . . ?
O11E Tb1 N14B 140.94(19) . . ?
O13C Tb1 N14A 141.06(19) . . ?
O11E Tb1 N14A 75.0(2) . . ?
N14B Tb1 N14A 80.1(2) . . ?
O13C Tb1 N1B 85.6(2) . . ?
O11E Tb1 N1B 79.68(19) . . ?
N14B Tb1 N1B 126.06(19) . . ?
N14A Tb1 N1B 82.0(2) . . ?
O13C Tb1 N1D 69.3(2) . . ?
O11E Tb1 N1D 69.5(2) . . ?
N14B Tb1 N1D 138.1(2) . . ?
N14A Tb1 N1D 141.5(2) . . ?
N1B Tb1 N1D 77.4(2) . . ?
O13C Tb1 N1A 80.26(19) . . ?
O11E Tb1 N1A 92.57(19) . . ?
N14B Tb1 N1A 78.07(19) . . ?
N14A Tb1 N1A 125.62(19) . . ?
N1B Tb1 N1A 148.6(2) . . ?
N1D Tb1 N1A 71.4(2) . . ?
O13C Tb1 N8A 134.9(2) . . ?
O11E Tb1 N8A 69.37(19) . . ?
N14B Tb1 N8A 73.10(18) . . ?
N14A Tb1 N8A 65.49(18) . . ?
N1B Tb1 N8A 139.5(2) . . ?
N1D Tb1 N8A 113.3(2) . . ?
N1A Tb1 N8A 60.65(18) . . ?
O13C Tb1 N8B 69.92(19) . . ?
O11E Tb1 N8B 130.99(19) . . ?
N14B Tb1 N8B 65.07(18) . . ?
N14A Tb1 N8B 71.8(2) . . ?
N1B Tb1 N8B 61.02(18) . . ?
N1D Tb1 N8B 122.8(2) . . ?
N1A Tb1 N8B 136.18(18) . . ?
N8A Tb1 N8B 123.90(19) . . ?
C2A N1A C6A 117.6(7) . . ?
C2A N1A Tb1 122.4(5) . . ?
C6A N1A Tb1 119.8(5) . . ?
N1A C2A C3A 124.0(7) . . ?
N1A C2A N7A 119.0(6) . . ?
C3A C2A N7A 117.0(7) . . ?
C4A C3A C2A 116.4(9) . . ?
C3A C4A C5A 120.9(9) . . ?
C6A C5A C4A 117.9(9) . . ?
C5A C6A N1A 122.9(8) . . ?
N8A N7A C2A 113.8(5) . . ?
N8A N7A C71A 121.7(6) . . ?
C2A N7A C71A 124.2(6) . . ?
C9A N8A N7A 119.0(6) . . ?
C9A N8A Tb1 117.6(5) . . ?
N7A N8A Tb1 122.7(4) . . ?
N8A C9A C10A 116.0(6) . . ?
N14A C10A N11A 111.9(7) . . ?
N14A C10A C9A 124.1(6) . . ?
N11A C10A C9A 124.1(7) . . ?
C10A N11A C12A 106.0(7) . . ?
C10A N11A C11A 127.0(8) . . ?
C12A N11A C11A 126.9(7) . . ?
C13A C12A N11A 107.4(7) . . ?
C12A C13A N14A 109.4(8) . . ?
C10A N14A C13A 105.4(7) . . ?
C10A N14A Tb1 116.2(5) . . ?
C13A N14A Tb1 137.7(5) . . ?
C2B N1B C6B 118.3(7) . . ?
C2B N1B Tb1 122.6(5) . . ?
C6B N1B Tb1 118.9(5) . . ?
N1B C2B N7B 118.2(6) . . ?
N1B C2B C3B 121.7(7) . . ?
N7B C2B C3B 120.1(7) . . ?
C4B C3B C2B 118.0(8) . . ?
C3B C4B C5B 121.2(9) . . ?
C4B C5B C6B 117.1(8) . . ?
N1B C6B C5B 123.6(8) . . ?
N8B N7B C2B 115.8(6) . . ?
N8B N7B C71B 119.6(6) . . ?
C2B N7B C71B 124.5(7) . . ?
C9B N8B N7B 119.9(6) . . ?
C9B N8B Tb1 118.1(5) . . ?
N7B N8B Tb1 122.0(4) . . ?
N8B C9B C10B 116.4(6) . . ?
N14B C10B N11B 111.2(6) . . ?
N14B C10B C9B 122.8(6) . . ?
N11B C10B C9B 126.0(6) . . ?
C10B N11B C12B 106.8(6) . . ?
C10B N11B C11B 126.3(7) . . ?
C12B N11B C11B 126.8(7) . . ?
C13B C12B N11B 106.4(7) . . ?
C12B C13B N14B 110.5(7) . . ?
C10B N14B C13B 105.1(6) . . ?
C10B N14B Tb1 116.7(5) . . ?
C13B N14B Tb1 137.1(5) . . ?
O11C S1C O12C 114.6(8) . . ?
O11C S1C O13C 114.7(6) . . ?
O12C S1C O13C 114.1(5) . . ?
O11C S1C C1C 103.8(9) . . ?
O12C S1C C1C 101.4(8) . . ?
O13C S1C C1C 106.3(5) . . ?
S1C O13C Tb1 162.1(3) . . ?
F12C C1C F13C 108.4(13) . . ?
F12C C1C F11C 96.3(13) . . ?
F13C C1C F11C 108.7(14) . . ?
F12C C1C S1C 113.9(12) . . ?
F13C C1C S1C 116.5(10) . . ?
F11C C1C S1C 111.0(11) . . ?
C2D N1D Tb1 165.6(8) . . ?
N1D C2D C3D 179.2(16) . . ?
O12E S1E O11E 122.6(6) . . ?
O12E S1E O13E 96.4(7) . . ?
O11E S1E O13E 103.1(5) . . ?
O12E S1E C1E 123.6(6) . . ?
O11E S1E C1E 109.1(5) . . ?
O13E S1E C1E 92.2(6) . . ?
S1E O11E Tb1 155.5(4) . . ?
F13E C1E F11E 119.3(12) . . ?
F13E C1E F12E 124.8(12) . . ?
F11E C1E F12E 105.6(11) . . ?
F13E C1E S1E 94.3(8) . . ?
F11E C1E S1E 104.5(8) . . ?
F12E C1E S1E 104.4(8) . . ?
O13F S1F O12F 115.9(5) . . ?
O13F S1F O11F 115.2(5) . . ?
O12F S1F O11F 113.2(5) . . ?
O13F S1F C1F 103.2(5) . . ?
O12F S1F C1F 104.3(6) . . ?
O11F S1F C1F 102.8(5) . . ?
F12F C1F F13F 109.7(13) . . ?
F12F C1F F11F 104.8(13) . . ?
F13F C1F F11F 105.9(11) . . ?
F12F C1F S1F 112.4(10) . . ?
F13F C1F S1F 112.3(9) . . ?
F11F C1F S1F 111.3(10) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6A N1A C2A C3A 1.2(12) . . . . ?
Tb1 N1A C2A C3A -173.8(7) . . . . ?
C6A N1A C2A N7A -177.3(7) . . . . ?
Tb1 N1A C2A N7A 7.7(9) . . . . ?
N1A C2A C3A C4A 2.4(17) . . . . ?
N7A C2A C3A C4A -179.1(11) . . . . ?
C2A C3A C4A C5A -2(2) . . . . ?
C3A C4A C5A C6A -1(2) . . . . ?
C4A C5A C6A N1A 5(2) . . . . ?
C2A N1A C6A C5A -5.3(14) . . . . ?
Tb1 N1A C6A C5A 169.9(9) . . . . ?
N1A C2A N7A N8A 2.6(10) . . . . ?
C3A C2A N7A N8A -176.0(8) . . . . ?
N1A C2A N7A C71A -171.2(8) . . . . ?
C3A C2A N7A C71A 10.2(13) . . . . ?
C2A N7A N8A C9A 177.9(7) . . . . ?
C71A N7A N8A C9A -8.1(11) . . . . ?
C2A N7A N8A Tb1 -11.8(8) . . . . ?
C71A N7A N8A Tb1 162.1(7) . . . . ?
N7A N8A C9A C10A 176.8(7) . . . . ?
Tb1 N8A C9A C10A 6.1(9) . . . . ?
N8A C9A C10A N14A -0.1(12) . . . . ?
N8A C9A C10A N11A -178.3(7) . . . . ?
N14A C10A N11A C12A -1.0(10) . . . . ?
C9A C10A N11A C12A 177.4(8) . . . . ?
N14A C10A N11A C11A -177.7(9) . . . . ?
C9A C10A N11A C11A 0.8(14) . . . . ?
C10A N11A C12A C13A 1.4(10) . . . . ?
C11A N11A C12A C13A 178.1(9) . . . . ?
N11A C12A C13A N14A -1.3(11) . . . . ?
N11A C10A N14A C13A 0.2(9) . . . . ?
C9A C10A N14A C13A -178.2(8) . . . . ?
N11A C10A N14A Tb1 172.3(5) . . . . ?
C9A C10A N14A Tb1 -6.1(10) . . . . ?
C12A C13A N14A C10A 0.7(10) . . . . ?
C12A C13A N14A Tb1 -168.8(7) . . . . ?
C6B N1B C2B N7B -177.6(8) . . . . ?
Tb1 N1B C2B N7B 6.5(10) . . . . ?
C6B N1B C2B C3B 1.4(12) . . . . ?
Tb1 N1B C2B C3B -174.4(6) . . . . ?
N1B C2B C3B C4B 0.4(14) . . . . ?
N7B C2B C3B C4B 179.4(9) . . . . ?
C2B C3B C4B C5B -3.2(16) . . . . ?
C3B C4B C5B C6B 4.0(16) . . . . ?
C2B N1B C6B C5B -0.5(13) . . . . ?
Tb1 N1B C6B C5B 175.5(7) . . . . ?
C4B C5B C6B N1B -2.2(14) . . . . ?
N1B C2B N7B N8B -7.3(11) . . . . ?
C3B C2B N7B N8B 173.7(8) . . . . ?
N1B C2B N7B C71B 177.0(9) . . . . ?
C3B C2B N7B C71B -2.0(13) . . . . ?
C2B N7B N8B C9B -173.8(7) . . . . ?
C71B N7B N8B C9B 2.2(12) . . . . ?
C2B N7B N8B Tb1 4.9(9) . . . . ?
C71B N7B N8B Tb1 -179.2(7) . . . . ?
N7B N8B C9B C10B 179.5(7) . . . . ?
Tb1 N8B C9B C10B 0.8(9) . . . . ?
N8B C9B C10B N14B 7.2(11) . . . . ?
N8B C9B C10B N11B -174.3(7) . . . . ?
N14B C10B N11B C12B 1.1(8) . . . . ?
C9B C10B N11B C12B -177.6(7) . . . . ?
N14B C10B N11B C11B -176.0(8) . . . . ?
C9B C10B N11B C11B 5.3(12) . . . . ?
C10B N11B C12B C13B -1.0(9) . . . . ?
C11B N11B C12B C13B 176.1(8) . . . . ?
N11B C12B C13B N14B 0.6(10) . . . . ?
N11B C10B N14B C13B -0.7(8) . . . . ?
C9B C10B N14B C13B 178.0(7) . . . . ?
N11B C10B N14B Tb1 169.8(4) . . . . ?
C9B C10B N14B Tb1 -11.5(9) . . . . ?
C12B C13B N14B C10B 0.1(9) . . . . ?
C12B C13B N14B Tb1 -167.5(6) . . . . ?
O11C S1C O13C Tb1 -109.2(14) . . . . ?
O12C S1C O13C Tb1 25.9(15) . . . . ?
C1C S1C O13C Tb1 136.8(14) . . . . ?
O11C S1C C1C F12C -173.0(13) . . . . ?
O12C S1C C1C F12C 67.8(13) . . . . ?
O13C S1C C1C F12C -51.7(14) . . . . ?
O11C S1C C1C F13C 59.6(17) . . . . ?
O12C S1C C1C F13C -59.5(17) . . . . ?
O13C S1C C1C F13C -179.1(14) . . . . ?
O11C S1C C1C F11C -65.6(14) . . . . ?
O12C S1C C1C F11C 175.2(13) . . . . ?
O13C S1C C1C F11C 55.7(14) . . . . ?
O12E S1E O11E Tb1 5.7(15) . . . . ?
O13E S1E O11E Tb1 -100.8(11) . . . . ?
C1E S1E O11E Tb1 162.2(9) . . . . ?
O12E S1E C1E F13E 79.7(12) . . . . ?
O11E S1E C1E F13E -76.5(9) . . . . ?
O13E S1E C1E F13E 178.8(9) . . . . ?
O12E S1E C1E F11E -42.1(13) . . . . ?
O11E S1E C1E F11E 161.7(9) . . . . ?
O13E S1E C1E F11E 57.1(10) . . . . ?
O12E S1E C1E F12E -152.7(10) . . . . ?
O11E S1E C1E F12E 51.1(10) . . . . ?
O13E S1E C1E F12E -53.6(9) . . . . ?
O13F S1F C1F F12F 179.9(12) . . . . ?
O12F S1F C1F F12F -58.6(13) . . . . ?
O11F S1F C1F F12F 59.8(13) . . . . ?
O13F S1F C1F F13F 55.6(10) . . . . ?
O12F S1F C1F F13F 177.1(9) . . . . ?
O11F S1F C1F F13F -64.6(10) . . . . ?
O13F S1F C1F F11F -62.9(10) . . . . ?
O12F S1F C1F F11F 58.6(10) . . . . ?
O11F S1F C1F F11F 177.0(9) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C3A H3A O12C 0.93 2.58 3.504(13) 171.7 4_565
C6A H6A O13C 0.93 2.46 3.122(10) 128.1 .
C71A H71B O12C 0.96 2.52 3.396(14) 152.1 4_565
C9A H9A O12F 0.93 2.42 3.148(10) 134.8 1_554
C12A H12A F12F 0.93 2.51 3.349(14) 149.7 3_656
C13A H13A O11F 0.93 2.44 3.268(10) 148.8 3_656
C6B H6B O11E 0.93 2.55 3.135(10) 121.4 .
C9B H9B O13F 0.93 2.52 3.410(10) 159.3 4_565
C11B H11D O13F 0.96 2.49 3.405(14) 159.6 4_565
C11B H11E O11F 0.96 2.35 3.253(11) 156.4 3_666

_refine_diff_density_max         1.713
_refine_diff_density_min         -1.256
_refine_diff_density_rms         0.129

_shelxl_version_number           2013-4

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_12
_database_code_depnum_ccdc_archive 'CCDC 1435580'
_audit_update_record             
;
2015-11-06 deposited with the CCDC.	2024-07-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H17 La N8 O10, C2 H3 N'
_chemical_formula_sum            'C14 H20 La N9 O10'
_chemical_formula_weight         613.30

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
La La -0.2871 2.4523 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.2733(4)
_cell_length_b                   11.4426(7)
_cell_length_c                   13.5163(7)
_cell_angle_alpha                109.919(6)
_cell_angle_beta                 106.972(4)
_cell_angle_gamma                93.483(4)
_cell_volume                     1132.21(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    130(1)
_cell_measurement_reflns_used    2932
_cell_measurement_theta_min      4.0660
_cell_measurement_theta_max      26.4710

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.799
_exptl_crystal_F_000             608
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.07
_exptl_absorpt_coefficient_mu    1.956
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.70198
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.34a (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?

_diffrn_ambient_temperature      130(1)
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Eos
_diffrn_detector_area_resol_mean 16.1544
_diffrn_measurement_method       ω-scan
_diffrn_reflns_number            5084
_diffrn_reflns_av_unetI/netI     0.0196
_diffrn_reflns_av_R_equivalents  0.0192
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.218
_diffrn_reflns_theta_max         26.531
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.721
_diffrn_measured_fraction_theta_full 0.795
_diffrn_reflns_Laue_measured_fraction_max 0.721
_diffrn_reflns_Laue_measured_fraction_full 0.795
_diffrn_reflns_point_group_measured_fraction_max 0.721
_diffrn_reflns_point_group_measured_fraction_full 0.795
_reflns_number_total             3393
_reflns_number_gt                3317
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlis Pro (Agilent Technologies (2011))'
_computing_cell_refinement       'CrysAlis Pro (Agilent Technologies (2011))'
_computing_data_reduction        'CrysAlis Pro (Agilent Technologies (2011))'
_computing_structure_solution    'SIR92 (Altomare et al., 1993)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Mercury (MacRae et al., 2009)'
_computing_publication_material  'SHELXL-2013 (Sheldrick, 2013)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0512P)²+0.2846P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3393
_refine_ls_number_parameters     315
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0227
_refine_ls_R_factor_gt           0.0218
_refine_ls_wR_factor_ref         0.0691
_refine_ls_wR_factor_gt          0.0683
_refine_ls_goodness_of_fit_ref   1.118
_refine_ls_restrained_S_all      1.118
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
La1 La 0.31327(2) 0.34366(2) 0.74634(2) 0.01169(8) Uani 1 1 d . . . . .
N1A N 0.0290(3) 0.4345(2) 0.6824(2) 0.0144(5) Uani 1 1 d . . . . .
C2A C -0.0334(4) 0.5031(3) 0.7610(3) 0.0184(7) Uani 1 1 d . . . . .
H2A H 0.0318 0.5230 0.8371 0.022 Uiso 1 1 calc R U . . .
C3A C -0.1854(4) 0.5459(3) 0.7374(3) 0.0206(7) Uani 1 1 d . . . . .
H3A H -0.2261 0.5926 0.7953 0.025 Uiso 1 1 calc R U . . .
C4A C -0.2787(4) 0.5189(3) 0.6256(3) 0.0204(7) Uani 1 1 d . . . . .
H4A H -0.3833 0.5491 0.6065 0.024 Uiso 1 1 calc R U . . .
C5A C -0.2198(4) 0.4491(3) 0.5438(3) 0.0180(7) Uani 1 1 d . . . . .
H5A H -0.2821 0.4311 0.4676 0.022 Uiso 1 1 calc R U . . .
C6A C -0.0659(4) 0.4043(3) 0.5739(2) 0.0134(6) Uani 1 1 d . . . . .
N7A N -0.0035(3) 0.3293(3) 0.4943(2) 0.0161(6) Uani 1 1 d . . . . .
C71A C -0.1042(4) 0.2759(3) 0.3755(2) 0.0186(7) Uani 1 1 d . . . . .
H71C H -0.0581 0.3205 0.3365 0.028 Uiso 1 1 calc R U . . .
H71B H -0.2242 0.2854 0.3657 0.028 Uiso 1 1 calc R U . . .
H71A H -0.0978 0.1861 0.3447 0.028 Uiso 1 1 calc R U . . .
N8A N 0.1564(3) 0.3022(2) 0.5300(2) 0.0138(5) Uani 1 1 d . . . . .
C9A C 0.2272(4) 0.2431(3) 0.4588(2) 0.0143(6) Uani 1 1 d . . . . .
H9A H 0.1711 0.2184 0.3808 0.017 Uiso 1 1 calc R U . . .
C10A C 0.3956(4) 0.2161(3) 0.5029(3) 0.0150(6) Uani 1 1 d . . . . .
N11A N 0.4816(3) 0.1444(2) 0.4404(2) 0.0167(6) Uani 1 1 d . . . . .
C11A C 0.4229(4) 0.0811(3) 0.3195(3) 0.0256(8) Uani 1 1 d . . . . .
H11 H 0.3065 0.0331 0.2937 0.038 Uiso 1 1 calc R U . . .
H11B H 0.5005 0.0235 0.2980 0.038 Uiso 1 1 calc R U . . .
H11A H 0.4223 0.1442 0.2854 0.038 Uiso 1 1 calc R U . . .
C12A C 0.6337(4) 0.1384(3) 0.5128(3) 0.0185(7) Uani 1 1 d . . . . .
H12A H 0.7213 0.0950 0.4938 0.022 Uiso 1 1 calc R U . . .
C13A C 0.6338(4) 0.2068(3) 0.6168(3) 0.0180(7) Uani 1 1 d . . . . .
H13A H 0.7238 0.2191 0.6839 0.022 Uiso 1 1 calc R U . . .
N14A N 0.4858(3) 0.2556(2) 0.6113(2) 0.0157(5) Uani 1 1 d . . . . .
N1B N 0.0814(3) 0.0873(3) 0.6492(2) 0.0219(6) Uani 1 1 d . . . . .
O11B O 0.2420(3) 0.0967(2) 0.6683(2) 0.0293(6) Uani 1 1 d . . . . .
O12B O 0.0264(3) 0.1896(2) 0.6803(2) 0.0227(5) Uani 1 1 d . . . . .
O13B O -0.0147(3) -0.0145(2) 0.6036(3) 0.0445(8) Uani 1 1 d . . . . .
N1C N 0.4075(3) 0.6269(3) 0.8073(2) 0.0182(6) Uani 1 1 d . . . . .
O11C O 0.4055(3) 0.5459(2) 0.71550(18) 0.0189(5) Uani 1 1 d . . . . .
O12C O 0.3645(3) 0.5866(2) 0.87452(18) 0.0205(5) Uani 1 1 d . . . . .
O13C O 0.4488(3) 0.7407(2) 0.8310(2) 0.0316(6) Uani 1 1 d . . . . .
N1D N 0.6682(3) 0.3344(3) 0.8960(2) 0.0204(6) Uani 1 1 d . . . . .
O11D O 0.5565(3) 0.2361(2) 0.84269(19) 0.0245(5) Uani 1 1 d . . . . .
O12D O 0.6213(3) 0.4381(2) 0.89050(18) 0.0209(5) Uani 1 1 d . . . . .
O13D O 0.8149(3) 0.3345(3) 0.9499(2) 0.0353(7) Uani 1 1 d . . . . .
O1E O 0.2443(3) 0.3549(3) 0.9175(2) 0.0227(6) Uani 1 1 d . . . . .
H1E H 0.285(5) 0.408(4) 0.967(3) 0.016(10) Uiso 1 1 d . . . . .
C1E C 0.1959(5) 0.2506(4) 0.9453(3) 0.0312(9) Uani 1 1 d . . . . .
H1E3 H 0.1248 0.1805 0.8771 0.047 Uiso 1 1 calc R U . . .
H1E2 H 0.1305 0.2769 0.9966 0.047 Uiso 1 1 calc R U . . .
H1E1 H 0.2993 0.2231 0.9811 0.047 Uiso 1 1 calc R U . . .
N1F N 0.0205(5) 0.1103(5) 0.1551(3) 0.0634(13) Uani 1 1 d . . . . .
C2F C -0.1035(5) 0.0899(4) 0.0851(3) 0.0374(9) Uani 1 1 d . . . . .
C3F C -0.2650(6) 0.0627(4) -0.0052(4) 0.0453(11) Uani 1 1 d . . . . .
H3F3 H -0.3068 -0.0287 -0.0395 0.068 Uiso 1 1 calc R U . . .
H3F2 H -0.2472 0.0933 -0.0614 0.068 Uiso 1 1 calc R U . . .
H3F1 H -0.3497 0.1052 0.0244 0.068 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
La1 O1E 2.505(2) . ?
La1 O12B 2.593(2) . ?
La1 O11C 2.596(2) . ?
La1 O12D 2.606(2) . ?
La1 N14A 2.612(3) . ?
La1 O11B 2.617(2) . ?
La1 O12C 2.657(2) . ?
La1 N1A 2.661(2) . ?
La1 O11D 2.669(2) . ?
La1 N8A 2.687(2) . ?
La1 N1B 3.038(3) . ?
La1 N1C 3.048(3) . ?
N1A C2A 1.347(4) . ?
N1A C6A 1.355(4) . ?
C2A C3A 1.367(4) . ?
C2A H2A 0.9500 . ?
C3A C4A 1.395(4) . ?
C3A H3A 0.9500 . ?
C4A C5A 1.362(5) . ?
C4A H4A 0.9500 . ?
C5A C6A 1.403(4) . ?
C5A H5A 0.9500 . ?
C6A N7A 1.382(4) . ?
N7A N8A 1.364(3) . ?
N7A C71A 1.460(4) . ?
C71A H71C 0.9800 . ?
C71A H71B 0.9800 . ?
C71A H71A 0.9800 . ?
N8A C9A 1.289(4) . ?
C9A C10A 1.444(4) . ?
C9A H9A 0.9500 . ?
C10A N14A 1.333(4) . ?
C10A N11A 1.358(4) . ?
N11A C12A 1.372(4) . ?
N11A C11A 1.455(4) . ?
C11A H11 0.9800 . ?
C11A H11B 0.9800 . ?
C11A H11A 0.9800 . ?
C12A C13A 1.356(5) . ?
C12A H12A 0.9500 . ?
C13A N14A 1.370(4) . ?
C13A H13A 0.9500 . ?
N1B O13B 1.217(4) . ?
N1B O12B 1.263(3) . ?
N1B O11B 1.268(4) . ?
N1C O13C 1.230(3) . ?
N1C O11C 1.266(4) . ?
N1C O12C 1.272(3) . ?
N1D O13D 1.219(3) . ?
N1D O11D 1.253(4) . ?
N1D O12D 1.290(3) . ?
O1E C1E 1.435(4) . ?
O1E H1E 0.71(4) . ?
C1E H1E3 0.9800 . ?
C1E H1E2 0.9800 . ?
C1E H1E1 0.9800 . ?
N1F C2F 1.121(5) . ?
C2F C3F 1.452(5) . ?
C3F H3F3 0.9800 . ?
C3F H3F2 0.9800 . ?
C3F H3F1 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1E La1 O12B 72.93(8) . . ?
O1E La1 O11C 121.73(8) . . ?
O12B La1 O11C 134.78(6) . . ?
O1E La1 O12D 82.29(8) . . ?
O12B La1 O12D 148.35(6) . . ?
O11C La1 O12D 75.28(6) . . ?
O1E La1 N14A 148.95(8) . . ?
O12B La1 N14A 109.59(8) . . ?
O11C La1 N14A 79.47(7) . . ?
O12D La1 N14A 82.05(7) . . ?
O1E La1 O11B 90.57(9) . . ?
O12B La1 O11B 48.74(7) . . ?
O11C La1 O11B 147.68(8) . . ?
O12D La1 O11B 113.81(7) . . ?
N14A La1 O11B 71.69(8) . . ?
O1E La1 O12C 72.95(8) . . ?
O12B La1 O12C 123.58(7) . . ?
O11C La1 O12C 48.82(7) . . ?
O12D La1 O12C 64.42(7) . . ?
N14A La1 O12C 122.67(7) . . ?
O11B La1 O12C 163.51(8) . . ?
O1E La1 N1A 88.34(8) . . ?
O12B La1 N1A 64.18(7) . . ?
O11C La1 N1A 73.27(7) . . ?
O12D La1 N1A 135.57(8) . . ?
N14A La1 N1A 121.23(7) . . ?
O11B La1 N1A 109.60(8) . . ?
O12C La1 N1A 71.29(7) . . ?
O1E La1 O11D 77.74(8) . . ?
O12B La1 O11D 105.90(7) . . ?
O11C La1 O11D 118.71(7) . . ?
O12D La1 O11D 48.40(7) . . ?
N14A La1 O11D 71.81(7) . . ?
O11B La1 O11D 65.71(7) . . ?
O12C La1 O11D 108.99(7) . . ?
N1A La1 O11D 165.06(8) . . ?
O1E La1 N8A 140.59(8) . . ?
O12B La1 N8A 72.87(7) . . ?
O11C La1 N8A 72.77(7) . . ?
O12D La1 N8A 136.18(7) . . ?
N14A La1 N8A 63.33(7) . . ?
O11B La1 N8A 81.31(8) . . ?
O12C La1 N8A 111.66(7) . . ?
N1A La1 N8A 59.21(8) . . ?
O11D La1 N8A 130.72(8) . . ?
O1E La1 N1B 82.15(8) . . ?
O12B La1 N1B 24.31(7) . . ?
O11C La1 N1B 147.08(7) . . ?
O12D La1 N1B 134.41(6) . . ?
N14A La1 N1B 89.98(8) . . ?
O11B La1 N1B 24.48(7) . . ?
O12C La1 N1B 146.58(8) . . ?
N1A La1 N1B 86.34(7) . . ?
O11D La1 N1B 86.42(7) . . ?
N8A La1 N1B 74.63(7) . . ?
O1E La1 N1C 97.50(8) . . ?
O12B La1 N1C 134.06(7) . . ?
O11C La1 N1C 24.26(7) . . ?
O12D La1 N1C 67.56(6) . . ?
N14A La1 N1C 101.01(8) . . ?
O11B La1 N1C 171.93(8) . . ?
O12C La1 N1C 24.56(7) . . ?
N1A La1 N1C 70.85(7) . . ?
O11D La1 N1C 115.93(7) . . ?
N8A La1 N1C 92.39(7) . . ?
N1B La1 N1C 157.17(7) . . ?
C2A N1A C6A 118.0(3) . . ?
C2A N1A La1 118.53(17) . . ?
C6A N1A La1 123.1(2) . . ?
N1A C2A C3A 123.6(3) . . ?
N1A C2A H2A 118.2 . . ?
C3A C2A H2A 118.2 . . ?
C2A C3A C4A 117.9(3) . . ?
C2A C3A H3A 121.0 . . ?
C4A C3A H3A 121.0 . . ?
C5A C4A C3A 120.0(3) . . ?
C5A C4A H4A 120.0 . . ?
C3A C4A H4A 120.0 . . ?
C4A C5A C6A 119.0(3) . . ?
C4A C5A H5A 120.5 . . ?
C6A C5A H5A 120.5 . . ?
N1A C6A N7A 117.3(3) . . ?
N1A C6A C5A 121.2(3) . . ?
N7A C6A C5A 121.5(3) . . ?
N8A N7A C6A 117.8(2) . . ?
N8A N7A C71A 119.7(3) . . ?
C6A N7A C71A 122.5(2) . . ?
N7A C71A H71C 109.5 . . ?
N7A C71A H71B 109.5 . . ?
H71C C71A H71B 109.5 . . ?
N7A C71A H71A 109.5 . . ?
H71C C71A H71A 109.5 . . ?
H71B C71A H71A 109.5 . . ?
C9A N8A N7A 120.2(2) . . ?
C9A N8A La1 118.35(17) . . ?
N7A N8A La1 121.00(18) . . ?
N8A C9A C10A 117.0(3) . . ?
N8A C9A H9A 121.5 . . ?
C10A C9A H9A 121.5 . . ?
N14A C10A N11A 110.7(3) . . ?
N14A C10A C9A 124.3(3) . . ?
N11A C10A C9A 124.9(3) . . ?
C10A N11A C12A 107.2(3) . . ?
C10A N11A C11A 127.1(3) . . ?
C12A N11A C11A 125.7(3) . . ?
N11A C11A H11 109.5 . . ?
N11A C11A H11B 109.5 . . ?
H11 C11A H11B 109.5 . . ?
N11A C11A H11A 109.5 . . ?
H11 C11A H11A 109.5 . . ?
H11B C11A H11A 109.5 . . ?
C13A C12A N11A 106.2(3) . . ?
C13A C12A H12A 126.9 . . ?
N11A C12A H12A 126.9 . . ?
C12A C13A N14A 110.3(3) . . ?
C12A C13A H13A 124.8 . . ?
N14A C13A H13A 124.8 . . ?
C10A N14A C13A 105.5(3) . . ?
C10A N14A La1 115.27(19) . . ?
C13A N14A La1 136.59(19) . . ?
O13B N1B O12B 121.7(3) . . ?
O13B N1B O11B 122.0(3) . . ?
O12B N1B O11B 116.3(2) . . ?
O13B N1B La1 175.7(2) . . ?
O12B N1B La1 57.68(13) . . ?
O11B N1B La1 58.79(15) . . ?
N1B O11B La1 96.73(18) . . ?
N1B O12B La1 98.01(16) . . ?
O13C N1C O11C 121.5(3) . . ?
O13C N1C O12C 120.9(3) . . ?
O11C N1C O12C 117.6(2) . . ?
O13C N1C La1 178.5(3) . . ?
O11C N1C La1 57.44(13) . . ?
O12C N1C La1 60.23(15) . . ?
N1C O11C La1 98.30(15) . . ?
N1C O12C La1 95.21(19) . . ?
O13D N1D O11D 123.1(3) . . ?
O13D N1D O12D 120.4(3) . . ?
O11D N1D O12D 116.5(2) . . ?
N1D O11D La1 96.44(16) . . ?
N1D O12D La1 98.43(16) . . ?
C1E O1E La1 127.0(2) . . ?
C1E O1E H1E 109(3) . . ?
La1 O1E H1E 118(3) . . ?
O1E C1E H1E3 109.5 . . ?
O1E C1E H1E2 109.5 . . ?
H1E3 C1E H1E2 109.5 . . ?
O1E C1E H1E1 109.5 . . ?
H1E3 C1E H1E1 109.5 . . ?
H1E2 C1E H1E1 109.5 . . ?
N1F C2F C3F 179.4(5) . . ?
C2F C3F H3F3 109.5 . . ?
C2F C3F H3F2 109.5 . . ?
H3F3 C3F H3F2 109.5 . . ?
C2F C3F H3F1 109.5 . . ?
H3F3 C3F H3F1 109.5 . . ?
H3F2 C3F H3F1 109.5 . . ?

_refine_diff_density_max         0.662
_refine_diff_density_min         -1.015
_refine_diff_density_rms         0.110

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_13
_database_code_depnum_ccdc_archive 'CCDC 1052302'
_audit_update_record             
;
2016-01-10 deposited with the CCDC.	2024-07-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H17 N8 O10 Pr, 0.5(C H4 O)'
_chemical_formula_sum            'C12.50 H19 N8 O10.50 Pr'
_chemical_formula_weight         590.27

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Pr Pr -0.2180 2.8214 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.1238(3)
_cell_length_b                   10.5711(7)
_cell_length_c                   12.6360(5)
_cell_angle_alpha                99.359(4)
_cell_angle_beta                 97.224(4)
_cell_angle_gamma                100.751(4)
_cell_volume                     1038.18(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(1)
_cell_measurement_reflns_used    4339
_cell_measurement_theta_min      3.4650
_cell_measurement_theta_max      26.7700

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.888
_exptl_crystal_F_000             586
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.12
_exptl_absorpt_coefficient_mu    2.418
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.56075
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(1)
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Eos
_diffrn_detector_area_resol_mean 16.1544
_diffrn_measurement_method       ω-scan
_diffrn_reflns_number            6734
_diffrn_reflns_av_unetI/netI     0.0220
_diffrn_reflns_av_R_equivalents  0.0187
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.335
_diffrn_reflns_theta_max         26.793
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.904
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.904
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.904
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             4006
_reflns_number_gt                3893
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlis Pro (Agilent Technologies (2011))'
_computing_cell_refinement       'CrysAlis Pro (Agilent Technologies (2011))'
_computing_data_reduction        'CrysAlis Pro (Agilent Technologies (2011))'
_computing_structure_solution    'SIR92 (Altomare et al., 1993)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Mercury (MacRae et al., 2009)'
_computing_publication_material  'SHELXL-2013 (Sheldrick, 2013)'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0382P)²+1.3066P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4006
_refine_ls_number_parameters     303
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0236
_refine_ls_R_factor_gt           0.0226
_refine_ls_wR_factor_ref         0.0630
_refine_ls_wR_factor_gt          0.0624
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_restrained_S_all      1.080
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Pr1 Pr 0.69568(2) 0.23296(2) 0.70948(2) 0.01151(7) Uani 1 1 d . . . . .
N1A N 0.9553(3) 0.3115(2) 0.61830(18) 0.0141(5) Uani 1 1 d . . . . .
C2A C 1.0382(4) 0.4369(3) 0.6364(2) 0.0136(5) Uani 1 1 d . . . . .
C3A C 1.1766(4) 0.4775(3) 0.5851(2) 0.0186(6) Uani 1 1 d . . . . .
H3A H 1.2306 0.5675 0.5967 0.022 Uiso 1 1 calc R U . . .
C4A C 1.2330(4) 0.3848(3) 0.5178(2) 0.0198(6) Uani 1 1 d . . . . .
H4A H 1.3268 0.4103 0.4824 0.024 Uiso 1 1 calc R U . . .
C5A C 1.1524(4) 0.2538(3) 0.5019(2) 0.0216(6) Uani 1 1 d . . . . .
H5A H 1.1912 0.1879 0.4571 0.026 Uiso 1 1 calc R U . . .
C6A C 1.0152(4) 0.2225(3) 0.5526(2) 0.0188(6) Uani 1 1 d . . . . .
H6A H 0.9587 0.1330 0.5409 0.023 Uiso 1 1 calc R U . . .
N7A N 0.9787(3) 0.5269(2) 0.70609(19) 0.0150(5) Uani 1 1 d . . . . .
C7A C 1.0654(4) 0.6641(3) 0.7404(2) 0.0179(6) Uani 1 1 d . . . . .
H7A3 H 1.0149 0.7169 0.6937 0.027 Uiso 1 1 calc R U . . .
H7A2 H 1.1860 0.6726 0.7347 0.027 Uiso 1 1 calc R U . . .
H7A1 H 1.0536 0.6950 0.8160 0.027 Uiso 1 1 calc R U . . .
N8A N 0.8240(3) 0.4839(2) 0.73410(18) 0.0126(5) Uani 1 1 d . . . . .
C9A C 0.7453(4) 0.5663(3) 0.7812(2) 0.0145(5) Uani 1 1 d . . . . .
H9A H 0.7919 0.6580 0.7973 0.017 Uiso 1 1 calc R U . . .
C10A C 0.5831(4) 0.5124(3) 0.8082(2) 0.0158(6) Uani 1 1 d . . . . .
N11A N 0.4898(3) 0.5821(2) 0.8663(2) 0.0179(5) Uani 1 1 d . . . . .
C11A C 0.5341(5) 0.7221(3) 0.9130(3) 0.0274(7) Uani 1 1 d . . . . .
H11C H 0.6462 0.7431 0.9585 0.041 Uiso 1 1 calc R U . . .
H11B H 0.4493 0.7446 0.9573 0.041 Uiso 1 1 calc R U . . .
H11A H 0.5366 0.7724 0.8544 0.041 Uiso 1 1 calc R U . . .
C12A C 0.3470(4) 0.4960(3) 0.8757(2) 0.0199(6) Uani 1 1 d . . . . .
H12A H 0.2574 0.5159 0.9127 0.024 Uiso 1 1 calc R U . . .
C13A C 0.3578(4) 0.3765(3) 0.8220(2) 0.0193(6) Uani 1 1 d . . . . .
H13A H 0.2751 0.2978 0.8146 0.023 Uiso 1 1 calc R U . . .
N14A N 0.5066(3) 0.3865(2) 0.7798(2) 0.0163(5) Uani 1 1 d . . . . .
N1B N 0.5846(3) 0.2260(2) 0.4710(2) 0.0197(5) Uani 1 1 d . . . . .
O11B O 0.5465(4) 0.2247(2) 0.37390(18) 0.0344(6) Uani 1 1 d . . . . .
O12B O 0.6231(3) 0.1253(2) 0.50445(17) 0.0213(5) Uani 1 1 d . . . . .
O13B O 0.5893(3) 0.3249(2) 0.54240(17) 0.0197(4) Uani 1 1 d . . . . .
N1C N 0.7672(4) -0.0230(3) 0.7518(2) 0.0254(6) Uani 1 1 d . . . . .
O11C O 0.8108(4) -0.1216(3) 0.7712(2) 0.0460(8) Uani 1 1 d . . . . .
O12C O 0.6920(3) 0.0421(2) 0.81531(17) 0.0212(4) Uani 1 1 d . . . . .
O13C O 0.7975(3) 0.0209(2) 0.66690(19) 0.0286(5) Uani 1 1 d . . . . .
N1D N 0.9257(3) 0.3099(3) 0.9233(2) 0.0209(5) Uani 1 1 d . . . . .
O11D O 1.0227(3) 0.3444(3) 1.00938(19) 0.0395(7) Uani 1 1 d . . . . .
O12D O 0.9751(3) 0.2654(2) 0.83622(17) 0.0223(5) Uani 1 1 d . . . . .
O13D O 0.7720(3) 0.3193(2) 0.91605(17) 0.0205(4) Uani 1 1 d . . . . .
O1E O 0.4090(3) 0.0853(2) 0.66224(18) 0.0229(5) Uani 1 1 d . . . . .
H1E H 0.3665 0.0587 0.5867 0.027 Uiso 1 1 calc R U . . .
C1E C 0.2983(6) 0.0343(4) 0.7334(4) 0.0460(10) Uani 1 1 d . . . . .
H1E1 H 0.2975 -0.0590 0.7303 0.069 Uiso 1 1 calc R U . . .
H1E2 H 0.1829 0.0452 0.7102 0.069 Uiso 1 1 calc R U . . .
H1E3 H 0.3393 0.0822 0.8081 0.069 Uiso 1 1 calc R U . . .
O1F O 0.2786(13) 0.9712(9) 0.9593(6) 0.075(2) Uani 0.5 1 d . . P . .
H1F H 0.3214 0.9786 1.0246 0.113 Uiso 0.5 1 calc R U P . .
C1F C 0.1138(15) 0.9877(11) 0.9535(8) 0.065(3) Uani 0.5 1 d . . P . .
H1F1 H 0.1110 1.0700 1.0011 0.097 Uiso 0.5 1 calc R U P . .
H1F2 H 0.0443 0.9142 0.9768 0.097 Uiso 0.5 1 calc R U P . .
H1F3 H 0.0686 0.9905 0.8784 0.097 Uiso 0.5 1 calc R U P . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Pr1 O1E 2.491(2) . ?
Pr1 O13C 2.532(2) . ?
Pr1 O12D 2.540(2) . ?
Pr1 N14A 2.567(2) . ?
Pr1 O13D 2.576(2) . ?
Pr1 O13B 2.583(2) . ?
Pr1 O12C 2.593(2) . ?
Pr1 N1A 2.595(2) . ?
Pr1 O12B 2.600(2) . ?
Pr1 N8A 2.615(2) . ?
Pr1 N1D 2.984(2) . ?
Pr1 N1C 2.987(3) . ?
N1A C2A 1.339(4) . ?
N1A C6A 1.353(4) . ?
C2A N7A 1.386(4) . ?
C2A C3A 1.400(4) . ?
C3A C4A 1.374(4) . ?
C3A H3A 0.9500 . ?
C4A C5A 1.388(5) . ?
C4A H4A 0.9500 . ?
C5A C6A 1.369(4) . ?
C5A H5A 0.9500 . ?
C6A H6A 0.9500 . ?
N7A N8A 1.364(3) . ?
N7A C7A 1.458(4) . ?
C7A H7A3 0.9800 . ?
C7A H7A2 0.9800 . ?
C7A H7A1 0.9800 . ?
N8A C9A 1.288(4) . ?
C9A C10A 1.440(4) . ?
C9A H9A 0.9500 . ?
C10A N14A 1.329(4) . ?
C10A N11A 1.352(4) . ?
N11A C12A 1.366(4) . ?
N11A C11A 1.460(4) . ?
C11A H11C 0.9800 . ?
C11A H11B 0.9800 . ?
C11A H11A 0.9800 . ?
C12A C13A 1.358(4) . ?
C12A H12A 0.9500 . ?
C13A N14A 1.373(4) . ?
C13A H13A 0.9500 . ?
N1B O11B 1.224(3) . ?
N1B O13B 1.256(3) . ?
N1B O12B 1.284(3) . ?
N1C O11C 1.213(4) . ?
N1C O12C 1.261(3) . ?
N1C O13C 1.270(4) . ?
N1D O11D 1.218(3) . ?
N1D O13D 1.264(3) . ?
N1D O12D 1.268(3) . ?
O1E C1E 1.445(5) . ?
O1E H1E 0.9500 . ?
C1E H1E1 0.9800 . ?
C1E H1E2 0.9800 . ?
C1E H1E3 0.9800 . ?
O1F C1F 1.376(14) . ?
O1F H1F 0.8400 . ?
C1F H1F1 0.9800 . ?
C1F H1F2 0.9800 . ?
C1F H1F3 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1E Pr1 O13C 83.51(8) . . ?
O1E Pr1 O12D 140.57(7) . . ?
O13C Pr1 O12D 74.26(8) . . ?
O1E Pr1 N14A 78.29(8) . . ?
O13C Pr1 N14A 157.65(8) . . ?
O12D Pr1 N14A 112.67(7) . . ?
O1E Pr1 O13D 110.88(7) . . ?
O13C Pr1 O13D 108.01(7) . . ?
O12D Pr1 O13D 49.83(7) . . ?
N14A Pr1 O13D 67.45(7) . . ?
O1E Pr1 O13B 82.86(7) . . ?
O13C Pr1 O13B 115.28(7) . . ?
O12D Pr1 O13B 136.06(7) . . ?
N14A Pr1 O13B 75.37(7) . . ?
O13D Pr1 O13B 135.87(7) . . ?
O1E Pr1 O12C 71.32(7) . . ?
O13C Pr1 O12C 49.69(7) . . ?
O12D Pr1 O12C 69.44(7) . . ?
N14A Pr1 O12C 111.22(7) . . ?
O13D Pr1 O12C 68.65(7) . . ?
O13B Pr1 O12C 150.77(7) . . ?
O1E Pr1 N1A 139.77(7) . . ?
O13C Pr1 N1A 79.71(8) . . ?
O12D Pr1 N1A 67.78(7) . . ?
N14A Pr1 N1A 122.63(8) . . ?
O13D Pr1 N1A 109.04(7) . . ?
O13B Pr1 N1A 72.01(7) . . ?
O12C Pr1 N1A 120.32(7) . . ?
O1E Pr1 O12B 67.69(7) . . ?
O13C Pr1 O12B 67.00(7) . . ?
O12D Pr1 O12B 127.92(7) . . ?
N14A Pr1 O12B 116.50(8) . . ?
O13D Pr1 O12B 174.78(6) . . ?
O13B Pr1 O12B 49.33(7) . . ?
O12C Pr1 O12B 106.29(7) . . ?
N1A Pr1 O12B 72.10(7) . . ?
O1E Pr1 N8A 137.37(7) . . ?
O13C Pr1 N8A 136.98(8) . . ?
O12D Pr1 N8A 76.26(7) . . ?
N14A Pr1 N8A 64.38(8) . . ?
O13D Pr1 N8A 74.01(7) . . ?
O13B Pr1 N8A 68.90(7) . . ?
O12C Pr1 N8A 140.18(7) . . ?
N1A Pr1 N8A 60.32(7) . . ?
O12B Pr1 N8A 110.57(7) . . ?
O1E Pr1 N1D 128.62(7) . . ?
O13C Pr1 N1D 91.33(8) . . ?
O12D Pr1 N1D 24.91(7) . . ?
N14A Pr1 N1D 89.99(8) . . ?
O13D Pr1 N1D 24.91(7) . . ?
O13B Pr1 N1D 142.26(7) . . ?
O12C Pr1 N1D 66.95(7) . . ?
N1A Pr1 N1D 88.26(7) . . ?
O12B Pr1 N1D 152.63(7) . . ?
N8A Pr1 N1D 73.39(7) . . ?
O1E Pr1 N1C 77.43(8) . . ?
O13C Pr1 N1C 24.89(7) . . ?
O12D Pr1 N1C 68.66(8) . . ?
N14A Pr1 N1C 135.53(8) . . ?
O13D Pr1 N1C 87.48(7) . . ?
O13B Pr1 N1C 136.58(7) . . ?
O12C Pr1 N1C 24.86(7) . . ?
N1A Pr1 N1C 99.64(8) . . ?
O12B Pr1 N1C 87.30(7) . . ?
N8A Pr1 N1C 144.41(8) . . ?
N1D Pr1 N1C 77.17(8) . . ?
C2A N1A C6A 117.7(2) . . ?
C2A N1A Pr1 122.88(18) . . ?
C6A N1A Pr1 119.42(19) . . ?
N1A C2A N7A 117.3(2) . . ?
N1A C2A C3A 122.0(3) . . ?
N7A C2A C3A 120.7(3) . . ?
C4A C3A C2A 118.8(3) . . ?
C4A C3A H3A 120.6 . . ?
C2A C3A H3A 120.6 . . ?
C3A C4A C5A 119.7(3) . . ?
C3A C4A H4A 120.1 . . ?
C5A C4A H4A 120.1 . . ?
C6A C5A C4A 117.9(3) . . ?
C6A C5A H5A 121.1 . . ?
C4A C5A H5A 121.1 . . ?
N1A C6A C5A 123.8(3) . . ?
N1A C6A H6A 118.1 . . ?
C5A C6A H6A 118.1 . . ?
N8A N7A C2A 116.3(2) . . ?
N8A N7A C7A 120.4(2) . . ?
C2A N7A C7A 123.0(2) . . ?
N7A C7A H7A3 109.5 . . ?
N7A C7A H7A2 109.5 . . ?
H7A3 C7A H7A2 109.5 . . ?
N7A C7A H7A1 109.5 . . ?
H7A3 C7A H7A1 109.5 . . ?
H7A2 C7A H7A1 109.5 . . ?
C9A N8A N7A 120.2(2) . . ?
C9A N8A Pr1 118.84(19) . . ?
N7A N8A Pr1 120.74(16) . . ?
N8A C9A C10A 116.5(3) . . ?
N8A C9A H9A 121.7 . . ?
C10A C9A H9A 121.7 . . ?
N14A C10A N11A 111.2(3) . . ?
N14A C10A C9A 124.0(3) . . ?
N11A C10A C9A 124.8(3) . . ?
C10A N11A C12A 107.0(2) . . ?
C10A N11A C11A 126.9(3) . . ?
C12A N11A C11A 126.1(3) . . ?
N11A C11A H11C 109.5 . . ?
N11A C11A H11B 109.5 . . ?
H11C C11A H11B 109.5 . . ?
N11A C11A H11A 109.5 . . ?
H11C C11A H11A 109.5 . . ?
H11B C11A H11A 109.5 . . ?
C13A C12A N11A 106.7(3) . . ?
C13A C12A H12A 126.7 . . ?
N11A C12A H12A 126.7 . . ?
C12A C13A N14A 109.7(3) . . ?
C12A C13A H13A 125.2 . . ?
N14A C13A H13A 125.2 . . ?
C10A N14A C13A 105.4(2) . . ?
C10A N14A Pr1 114.76(18) . . ?
C13A N14A Pr1 137.6(2) . . ?
O11B N1B O13B 122.3(3) . . ?
O11B N1B O12B 120.9(3) . . ?
O13B N1B O12B 116.8(2) . . ?
O11B N1B Pr1 177.3(2) . . ?
O13B N1B Pr1 57.95(14) . . ?
O12B N1B Pr1 58.90(13) . . ?
N1B O12B Pr1 96.09(16) . . ?
N1B O13B Pr1 97.71(16) . . ?
O11C N1C O12C 122.0(3) . . ?
O11C N1C O13C 121.4(3) . . ?
O12C N1C O13C 116.6(2) . . ?
O11C N1C Pr1 174.4(3) . . ?
O12C N1C Pr1 59.81(14) . . ?
O13C N1C Pr1 57.04(14) . . ?
N1C O12C Pr1 95.32(17) . . ?
N1C O13C Pr1 98.07(17) . . ?
O11D N1D O13D 121.7(3) . . ?
O11D N1D O12D 121.5(3) . . ?
O13D N1D O12D 116.7(2) . . ?
O11D N1D Pr1 178.0(2) . . ?
O13D N1D Pr1 59.18(14) . . ?
O12D N1D Pr1 57.55(14) . . ?
N1D O12D Pr1 97.54(16) . . ?
N1D O13D Pr1 95.90(16) . . ?
C1E O1E Pr1 129.2(2) . . ?
C1E O1E H1E 115.4 . . ?
Pr1 O1E H1E 115.4 . . ?
O1E C1E H1E1 109.5 . . ?
O1E C1E H1E2 109.5 . . ?
H1E1 C1E H1E2 109.5 . . ?
O1E C1E H1E3 109.5 . . ?
H1E1 C1E H1E3 109.5 . . ?
H1E2 C1E H1E3 109.5 . . ?
C1F O1F H1F 109.5 . . ?
O1F C1F H1F1 109.5 . . ?
O1F C1F H1F2 109.5 . . ?
H1F1 C1F H1F2 109.5 . . ?
O1F C1F H1F3 109.5 . . ?
H1F1 C1F H1F3 109.5 . . ?
H1F2 C1F H1F3 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6A N1A C2A N7A -178.3(2) . . . . ?
Pr1 N1A C2A N7A -0.8(3) . . . . ?
C6A N1A C2A C3A 3.4(4) . . . . ?
Pr1 N1A C2A C3A -179.1(2) . . . . ?
N1A C2A C3A C4A -2.7(4) . . . . ?
N7A C2A C3A C4A 179.1(3) . . . . ?
C2A C3A C4A C5A 0.1(4) . . . . ?
C3A C4A C5A C6A 1.6(5) . . . . ?
C2A N1A C6A C5A -1.6(4) . . . . ?
Pr1 N1A C6A C5A -179.2(2) . . . . ?
C4A C5A C6A N1A -0.9(5) . . . . ?
N1A C2A N7A N8A -11.5(4) . . . . ?
C3A C2A N7A N8A 166.8(2) . . . . ?
N1A C2A N7A C7A 174.4(2) . . . . ?
C3A C2A N7A C7A -7.3(4) . . . . ?
C2A N7A N8A C9A -167.0(3) . . . . ?
C7A N7A N8A C9A 7.3(4) . . . . ?
C2A N7A N8A Pr1 18.6(3) . . . . ?
C7A N7A N8A Pr1 -167.11(19) . . . . ?
N7A N8A C9A C10A -179.8(2) . . . . ?
Pr1 N8A C9A C10A -5.3(3) . . . . ?
N8A C9A C10A N14A -5.5(4) . . . . ?
N8A C9A C10A N11A 173.7(3) . . . . ?
N14A C10A N11A C12A 0.2(3) . . . . ?
C9A C10A N11A C12A -179.0(3) . . . . ?
N14A C10A N11A C11A 178.8(3) . . . . ?
C9A C10A N11A C11A -0.5(5) . . . . ?
C10A N11A C12A C13A -0.5(3) . . . . ?
C11A N11A C12A C13A -179.0(3) . . . . ?
N11A C12A C13A N14A 0.6(3) . . . . ?
N11A C10A N14A C13A 0.1(3) . . . . ?
C9A C10A N14A C13A 179.4(3) . . . . ?
N11A C10A N14A Pr1 -166.18(18) . . . . ?
C9A C10A N14A Pr1 13.1(4) . . . . ?
C12A C13A N14A C10A -0.4(3) . . . . ?
C12A C13A N14A Pr1 161.0(2) . . . . ?
O11B N1B O12B Pr1 176.9(3) . . . . ?
O13B N1B O12B Pr1 -2.6(3) . . . . ?
O11B N1B O13B Pr1 -176.8(3) . . . . ?
O12B N1B O13B Pr1 2.6(3) . . . . ?
O11C N1C O12C Pr1 173.8(3) . . . . ?
O13C N1C O12C Pr1 -5.2(3) . . . . ?
O11C N1C O13C Pr1 -173.6(3) . . . . ?
O12C N1C O13C Pr1 5.4(3) . . . . ?
O11D N1D O12D Pr1 -177.9(3) . . . . ?
O13D N1D O12D Pr1 0.7(3) . . . . ?
O11D N1D O13D Pr1 177.9(3) . . . . ?
O12D N1D O13D Pr1 -0.7(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C3A H3A O11B 0.95 2.51 3.431(4) 162.2 2_766
C5A H5A O13C 0.95 2.51 3.434(4) 162.8 2_756
C6A H6A O13C 0.95 2.49 3.161(4) 127.4 .
C7A H7A1 O11D 0.98 2.44 3.340(4) 151.7 2_767
C9A H9A O11C 0.95 2.39 3.268(4) 154.3 1_565
C13A H13A O12D 0.95 2.45 3.151(4) 130.1 1_455
O1E H1E O12B 0.95 2.11 2.753(3) 123.3 2_656
C1E H1E3 O1F 0.98 2.45 3.051(9) 119.0 1_545
O1F H1F O12C 0.84 2.08 2.857(8) 152.8 2_667
C1F H1F3 O11C 0.98 2.34 3.057(11) 129.6 1_465

_refine_diff_density_max         1.073
_refine_diff_density_min         -0.629
_refine_diff_density_rms         0.099

_shelxl_version_number           2013-4

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_02a
_database_code_depnum_ccdc_archive 'CCDC 1052303'
_audit_update_record             
;
2016-01-10 deposited with the CCDC.	2024-07-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C25 H26 F9 N10 O9 Pr S3, C2 H3 N'
_chemical_formula_sum            'C27 H29 F9 N11 O9 Pr S3'
_chemical_formula_weight         1059.70

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Pr Pr -0.2180 2.8214 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   8.9742(4)
_cell_length_b                   14.0340(5)
_cell_length_c                   15.8971(6)
_cell_angle_alpha                90
_cell_angle_beta                 92.838(4)
_cell_angle_gamma                90
_cell_volume                     1999.69(14)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(1)
_cell_measurement_reflns_used    4060
_cell_measurement_theta_min      3.3110
_cell_measurement_theta_max      28.0530

_exptl_crystal_description       prism
_exptl_crystal_colour            pale-yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.760
_exptl_crystal_F_000             1056
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_absorpt_coefficient_mu    1.480
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.80557
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(1)
_diffrn_radiation_wavelength     0.7107
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_detector_area_resol_mean 16.1544
_diffrn_measurement_method       ω-scan
_diffrn_reflns_number            8138
_diffrn_reflns_av_unetI/netI     0.0634
_diffrn_reflns_av_R_equivalents  0.0426
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.937
_diffrn_reflns_theta_max         28.135
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.842
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.842
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.615
_diffrn_reflns_point_group_measured_fraction_full 0.752
_reflns_number_total             6021
_reflns_number_gt                5784
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.405
_reflns_Friedel_fraction_max     0.370
_reflns_Friedel_fraction_full    0.483

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlis Pro (Agilent Technologies (2011))'
_computing_cell_refinement       'CrysAlis Pro (Agilent Technologies (2011))'
_computing_data_reduction        'CrysAlis Pro (Agilent Technologies (2011))'
_computing_structure_solution    'SIR92 (Altomare et al., 1993)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Mercury (MacRae et al., 2009)'
_computing_publication_material  'SHELXL-2013 (Sheldrick, 2013)'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0417P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1619 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.037(11)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         6021
_refine_ls_number_parameters     546
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0394
_refine_ls_R_factor_gt           0.0368
_refine_ls_wR_factor_ref         0.0897
_refine_ls_wR_factor_gt          0.0866
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_restrained_S_all      1.071
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Pr1 Pr 0.85741(3) 0.24512(3) 0.73814(2) 0.01067(10) Uani 1 1 d . . . . .
N1A N 0.9793(6) 0.0778(5) 0.7594(4) 0.0157(13) Uani 1 1 d . . . . .
C2A C 1.0685(7) 0.0539(5) 0.8266(4) 0.0118(14) Uani 1 1 d . . . . .
C3A C 1.1257(8) -0.0388(6) 0.8365(5) 0.0183(16) Uani 1 1 d . . . . .
H3A H 1.1892 -0.0544 0.8841 0.022 Uiso 1 1 calc R U . . .
C4A C 1.0899(9) -0.1059(6) 0.7778(5) 0.0242(18) Uani 1 1 d . . . . .
H4A H 1.1269 -0.1690 0.7845 0.029 Uiso 1 1 calc R U . . .
C5A C 0.9986(8) -0.0821(6) 0.7077(5) 0.0219(17) Uani 1 1 d . . . . .
H5A H 0.9737 -0.1277 0.6651 0.026 Uiso 1 1 calc R U . . .
C6A C 0.9458(8) 0.0096(6) 0.7023(5) 0.0204(17) Uani 1 1 d . . . . .
H6A H 0.8815 0.0259 0.6552 0.024 Uiso 1 1 calc R U . . .
N7A N 1.1034(7) 0.1265(5) 0.8838(4) 0.0141(15) Uani 1 1 d . . . . .
C71A C 1.1887(8) 0.1092(6) 0.9631(5) 0.0201(17) Uani 1 1 d . . . . .
H71C H 1.2936 0.1256 0.9565 0.030 Uiso 1 1 calc R U . . .
H71B H 1.1810 0.0417 0.9784 0.030 Uiso 1 1 calc R U . . .
H71A H 1.1486 0.1486 1.0076 0.030 Uiso 1 1 calc R U . . .
N8A N 1.0707(6) 0.2161(4) 0.8582(4) 0.0130(13) Uani 1 1 d . . . . .
C9A C 1.1220(7) 0.2879(6) 0.9009(5) 0.0141(15) Uani 1 1 d . . . . .
H9A H 1.1883 0.2803 0.9489 0.017 Uiso 1 1 calc R U . . .
C10A C 1.0731(9) 0.3805(6) 0.8716(5) 0.0159(18) Uani 1 1 d . . . . .
N11A N 1.1141(7) 0.4643(5) 0.9075(4) 0.0192(14) Uani 1 1 d . . . . .
C11A C 1.2041(11) 0.4784(7) 0.9857(6) 0.037(2) Uani 1 1 d . . . . .
H11C H 1.1592 0.4436 1.0315 0.056 Uiso 1 1 calc R U . . .
H11B H 1.2082 0.5465 0.9994 0.056 Uiso 1 1 calc R U . . .
H11A H 1.3054 0.4546 0.9786 0.056 Uiso 1 1 calc R U . . .
C12A C 1.0471(8) 0.5355(6) 0.8605(5) 0.0189(16) Uani 1 1 d . . . . .
H12A H 1.0562 0.6022 0.8700 0.023 Uiso 1 1 calc R U . . .
C13A C 0.9652(8) 0.4919(6) 0.7977(5) 0.0198(16) Uani 1 1 d . . . . .
H13A H 0.9059 0.5237 0.7553 0.024 Uiso 1 1 calc R U . . .
N14A N 0.9806(6) 0.3945(5) 0.8046(4) 0.0147(13) Uani 1 1 d . . . . .
N1B N 0.6433(7) 0.3648(5) 0.7079(4) 0.0177(15) Uani 1 1 d . . . . .
C2B C 0.6471(8) 0.4388(6) 0.6534(5) 0.0182(16) Uani 1 1 d . . . . .
C3B C 0.5269(9) 0.5015(6) 0.6415(6) 0.030(2) Uani 1 1 d . . . . .
H3B H 0.5308 0.5532 0.6030 0.036 Uiso 1 1 calc R U . . .
C4B C 0.4043(10) 0.4863(7) 0.6865(6) 0.031(2) Uani 1 1 d . . . . .
H4B H 0.3209 0.5278 0.6792 0.037 Uiso 1 1 calc R U . . .
C5B C 0.3991(9) 0.4110(7) 0.7432(5) 0.0258(19) Uani 1 1 d . . . . .
H5B H 0.3142 0.4005 0.7754 0.031 Uiso 1 1 calc R U . . .
C6B C 0.5205(8) 0.3530(6) 0.7508(5) 0.0180(16) Uani 1 1 d . . . . .
H6B H 0.5177 0.3009 0.7889 0.022 Uiso 1 1 calc R U . . .
N7B N 0.7757(6) 0.4499(5) 0.6091(4) 0.0149(13) Uani 1 1 d . . . . .
C71B C 0.7951(8) 0.5237(6) 0.5456(5) 0.0218(17) Uani 1 1 d . . . . .
H71F H 0.8760 0.5666 0.5647 0.033 Uiso 1 1 calc R U . . .
H71E H 0.7023 0.5600 0.5372 0.033 Uiso 1 1 calc R U . . .
H71D H 0.8201 0.4938 0.4924 0.033 Uiso 1 1 calc R U . . .
N8B N 0.8866(6) 0.3847(4) 0.6255(4) 0.0142(13) Uani 1 1 d . . . . .
C9B C 1.0080(7) 0.3875(5) 0.5844(4) 0.0146(15) Uani 1 1 d . . . . .
H9B H 1.0234 0.4341 0.5423 0.018 Uiso 1 1 calc R U . . .
C10B C 1.1173(7) 0.3162(6) 0.6063(4) 0.0163(16) Uani 1 1 d . . . . .
N11B N 1.2448(6) 0.2989(5) 0.5660(4) 0.0185(14) Uani 1 1 d . . . . .
C11B C 1.2965(8) 0.3459(6) 0.4907(5) 0.0233(17) Uani 1 1 d . . . . .
H11F H 1.2530 0.3142 0.4404 0.035 Uiso 1 1 calc R U . . .
H11E H 1.4055 0.3423 0.4908 0.035 Uiso 1 1 calc R U . . .
H11D H 1.2655 0.4129 0.4906 0.035 Uiso 1 1 calc R U . . .
C12B C 1.3157(8) 0.2238(5) 0.6061(4) 0.0182(18) Uani 1 1 d . . . . .
H12B H 1.4075 0.1957 0.5921 0.022 Uiso 1 1 calc R U . . .
C13B C 1.2298(8) 0.1974(6) 0.6693(5) 0.0214(17) Uani 1 1 d . . . . .
H13B H 1.2518 0.1469 0.7078 0.026 Uiso 1 1 calc R U . . .
N14B N 1.1048(5) 0.2549(6) 0.6697(3) 0.0154(13) Uani 1 1 d . . . . .
S1C S 0.74271(19) 0.15130(14) 0.51222(11) 0.0162(4) Uani 1 1 d . . . . .
O11C O 0.8178(6) 0.0661(4) 0.4900(3) 0.0243(12) Uani 1 1 d . . . . .
O12C O 0.5829(6) 0.1507(5) 0.5008(4) 0.0360(16) Uani 1 1 d . . . . .
O13C O 0.8000(5) 0.1935(4) 0.5906(3) 0.0195(12) Uani 1 1 d . . . . .
C1C C 0.8000(9) 0.2355(8) 0.4335(4) 0.031(2) Uani 1 1 d . . . . .
F11C F 0.7589(7) 0.2071(4) 0.3561(3) 0.0485(15) Uani 1 1 d . . . . .
F12C F 0.7406(7) 0.3217(4) 0.4445(4) 0.0487(16) Uani 1 1 d . . . . .
F13C F 0.9489(5) 0.2459(6) 0.4374(3) 0.0454(13) Uani 1 1 d . . . . .
S1D S 0.77099(19) 0.28650(14) 0.96738(11) 0.0164(4) Uani 1 1 d . . . . .
O11D O 0.7802(6) 0.3889(4) 0.9681(4) 0.0297(14) Uani 1 1 d . . . . .
O12D O 0.8724(5) 0.2362(6) 1.0235(3) 0.0285(14) Uani 1 1 d . . . . .
O13D O 0.7548(4) 0.2451(5) 0.8831(2) 0.0158(9) Uani 1 1 d . . . . .
C1D C 0.5917(8) 0.2624(6) 1.0106(5) 0.023(2) Uani 1 1 d . . . . .
F11D F 0.5843(5) 0.3007(5) 1.0864(3) 0.0450(16) Uani 1 1 d . . . . .
F12D F 0.5653(5) 0.1685(4) 1.0165(3) 0.0346(13) Uani 1 1 d . . . . .
F13D F 0.4792(5) 0.2979(4) 0.9626(3) 0.0366(13) Uani 1 1 d . . . . .
S1E S 0.57197(19) 0.06093(14) 0.78909(11) 0.0150(4) Uani 1 1 d . . . . .
O11E O 0.4384(5) 0.0941(4) 0.8249(3) 0.0193(11) Uani 1 1 d . . . . .
O12E O 0.6742(6) 0.0078(4) 0.8431(3) 0.0224(12) Uani 1 1 d . . . . .
O13E O 0.6442(5) 0.1319(4) 0.7367(3) 0.0161(12) Uani 1 1 d . . . . .
C1E C 0.5060(8) -0.0281(6) 0.7112(5) 0.0203(17) Uani 1 1 d . . . . .
F11E F 0.4058(6) 0.0092(4) 0.6562(3) 0.0319(13) Uani 1 1 d . . . . .
F12E F 0.4444(5) -0.1009(3) 0.7484(3) 0.0312(11) Uani 1 1 d . . . . .
F13E F 0.6188(5) -0.0597(4) 0.6672(3) 0.0303(11) Uani 1 1 d . . . . .
N1F N 0.7904(12) 0.6900(7) 0.6949(6) 0.061(3) Uani 1 1 d . . . . .
C2F C 0.7776(12) 0.7274(11) 0.7580(7) 0.064(4) Uani 1 1 d . . . . .
C3F C 0.7676(14) 0.7773(10) 0.8430(8) 0.070(4) Uani 1 1 d . . . . .
H3F3 H 0.8642 0.7731 0.8743 0.106 Uiso 1 1 calc R U . . .
H3F2 H 0.6909 0.7464 0.8752 0.106 Uiso 1 1 calc R U . . .
H3F1 H 0.7413 0.8444 0.8338 0.106 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Pr1 O13C 2.484(5) . ?
Pr1 O13E 2.487(5) . ?
Pr1 N14B 2.524(5) . ?
Pr1 O13D 2.524(4) . ?
Pr1 N14A 2.573(6) . ?
Pr1 N1B 2.580(7) . ?
Pr1 N1A 2.606(6) . ?
Pr1 N8A 2.667(6) . ?
Pr1 N8B 2.676(6) . ?
N1A C6A 1.343(10) . ?
N1A C2A 1.345(9) . ?
C2A N7A 1.391(9) . ?
C2A C3A 1.405(11) . ?
C3A C4A 1.352(11) . ?
C3A H3A 0.9500 . ?
C4A C5A 1.391(10) . ?
C4A H4A 0.9500 . ?
C5A C6A 1.373(11) . ?
C5A H5A 0.9500 . ?
C6A H6A 0.9500 . ?
N7A N8A 1.350(9) . ?
N7A C71A 1.463(9) . ?
C71A H71C 0.9800 . ?
C71A H71B 0.9800 . ?
C71A H71A 0.9800 . ?
N8A C9A 1.287(9) . ?
C9A C10A 1.441(11) . ?
C9A H9A 0.9500 . ?
C10A N14A 1.332(9) . ?
C10A N11A 1.351(10) . ?
N11A C12A 1.369(10) . ?
N11A C11A 1.462(9) . ?
C11A H11C 0.9800 . ?
C11A H11B 0.9800 . ?
C11A H11A 0.9800 . ?
C12A C13A 1.356(10) . ?
C12A H12A 0.9500 . ?
C13A N14A 1.377(10) . ?
C13A H13A 0.9500 . ?
N1B C6B 1.336(10) . ?
N1B C2B 1.353(10) . ?
C2B N7B 1.390(9) . ?
C2B C3B 1.398(11) . ?
C3B C4B 1.360(13) . ?
C3B H3B 0.9500 . ?
C4B C5B 1.391(13) . ?
C4B H4B 0.9500 . ?
C5B C6B 1.360(11) . ?
C5B H5B 0.9500 . ?
C6B H6B 0.9500 . ?
N7B N8B 1.367(8) . ?
N7B C71B 1.462(10) . ?
C71B H71F 0.9800 . ?
C71B H71E 0.9800 . ?
C71B H71D 0.9800 . ?
N8B C9B 1.298(9) . ?
C9B C10B 1.432(10) . ?
C9B H9B 0.9500 . ?
C10B N14B 1.334(10) . ?
C10B N11B 1.362(9) . ?
N11B C12B 1.373(9) . ?
N11B C11B 1.461(9) . ?
C11B H11F 0.9800 . ?
C11B H11E 0.9800 . ?
C11B H11D 0.9800 . ?
C12B C13B 1.348(10) . ?
C12B H12B 0.9500 . ?
C13B N14B 1.382(9) . ?
C13B H13B 0.9500 . ?
S1C O11C 1.426(6) . ?
S1C O12C 1.437(5) . ?
S1C O13C 1.451(5) . ?
S1C C1C 1.814(10) . ?
C1C F11C 1.329(9) . ?
C1C F12C 1.336(12) . ?
C1C F13C 1.343(9) . ?
S1D O12D 1.429(6) . ?
S1D O11D 1.439(6) . ?
S1D O13D 1.460(5) . ?
S1D C1D 1.812(8) . ?
C1D F11D 1.324(9) . ?
C1D F13D 1.332(8) . ?
C1D F12D 1.342(10) . ?
S1E O11E 1.430(5) . ?
S1E O12E 1.433(5) . ?
S1E O13E 1.470(6) . ?
S1E C1E 1.836(8) . ?
C1E F12E 1.317(9) . ?
C1E F11E 1.330(9) . ?
C1E F13E 1.334(9) . ?
N1F C2F 1.143(14) . ?
C2F C3F 1.528(18) . ?
C3F H3F3 0.9800 . ?
C3F H3F2 0.9800 . ?
C3F H3F1 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O13C Pr1 O13E 71.41(17) . . ?
O13C Pr1 N14B 75.79(16) . . ?
O13E Pr1 N14B 136.3(2) . . ?
O13C Pr1 O13D 142.57(16) . . ?
O13E Pr1 O13D 72.14(18) . . ?
N14B Pr1 O13D 139.66(14) . . ?
O13C Pr1 N14A 133.66(19) . . ?
O13E Pr1 N14A 147.08(19) . . ?
N14B Pr1 N14A 76.3(2) . . ?
O13D Pr1 N14A 78.1(2) . . ?
O13C Pr1 N1B 84.04(19) . . ?
O13E Pr1 N1B 81.31(17) . . ?
N14B Pr1 N1B 123.2(2) . . ?
O13D Pr1 N1B 82.4(2) . . ?
N14A Pr1 N1B 81.2(2) . . ?
O13C Pr1 N1A 85.74(19) . . ?
O13E Pr1 N1A 75.12(18) . . ?
N14B Pr1 N1A 74.5(2) . . ?
O13D Pr1 N1A 93.0(2) . . ?
N14A Pr1 N1A 120.80(19) . . ?
N1B Pr1 N1A 156.2(2) . . ?
O13C Pr1 N8A 137.66(17) . . ?
O13E Pr1 N8A 115.73(17) . . ?
N14B Pr1 N8A 72.61(17) . . ?
O13D Pr1 N8A 68.16(15) . . ?
N14A Pr1 N8A 63.37(19) . . ?
N1B Pr1 N8A 137.3(2) . . ?
N1A Pr1 N8A 59.18(19) . . ?
O13C Pr1 N8B 66.69(18) . . ?
O13E Pr1 N8B 124.21(17) . . ?
N14B Pr1 N8B 63.6(2) . . ?
O13D Pr1 N8B 131.5(2) . . ?
N14A Pr1 N8B 67.92(19) . . ?
N1B Pr1 N8B 59.65(19) . . ?
N1A Pr1 N8B 133.82(18) . . ?
N8A Pr1 N8B 120.02(17) . . ?
C6A N1A C2A 117.6(7) . . ?
C6A N1A Pr1 118.4(5) . . ?
C2A N1A Pr1 123.9(5) . . ?
N1A C2A N7A 116.3(7) . . ?
N1A C2A C3A 121.3(7) . . ?
N7A C2A C3A 122.4(6) . . ?
C4A C3A C2A 119.6(7) . . ?
C4A C3A H3A 120.2 . . ?
C2A C3A H3A 120.2 . . ?
C3A C4A C5A 119.8(8) . . ?
C3A C4A H4A 120.1 . . ?
C5A C4A H4A 120.1 . . ?
C6A C5A C4A 117.5(7) . . ?
C6A C5A H5A 121.2 . . ?
C4A C5A H5A 121.2 . . ?
N1A C6A C5A 124.1(7) . . ?
N1A C6A H6A 117.9 . . ?
C5A C6A H6A 117.9 . . ?
N8A N7A C2A 116.5(6) . . ?
N8A N7A C71A 120.7(7) . . ?
C2A N7A C71A 122.3(7) . . ?
N7A C71A H71C 109.5 . . ?
N7A C71A H71B 109.5 . . ?
H71C C71A H71B 109.5 . . ?
N7A C71A H71A 109.5 . . ?
H71C C71A H71A 109.5 . . ?
H71B C71A H71A 109.5 . . ?
C9A N8A N7A 120.3(6) . . ?
C9A N8A Pr1 118.9(4) . . ?
N7A N8A Pr1 119.7(4) . . ?
N8A C9A C10A 116.1(6) . . ?
N8A C9A H9A 121.9 . . ?
C10A C9A H9A 121.9 . . ?
N14A C10A N11A 110.8(7) . . ?
N14A C10A C9A 124.0(8) . . ?
N11A C10A C9A 125.2(7) . . ?
C10A N11A C12A 107.6(6) . . ?
C10A N11A C11A 127.2(7) . . ?
C12A N11A C11A 125.1(7) . . ?
N11A C11A H11C 109.5 . . ?
N11A C11A H11B 109.5 . . ?
H11C C11A H11B 109.5 . . ?
N11A C11A H11A 109.5 . . ?
H11C C11A H11A 109.5 . . ?
H11B C11A H11A 109.5 . . ?
C13A C12A N11A 106.2(7) . . ?
C13A C12A H12A 126.9 . . ?
N11A C12A H12A 126.9 . . ?
C12A C13A N14A 109.9(7) . . ?
C12A C13A H13A 125.0 . . ?
N14A C13A H13A 125.0 . . ?
C10A N14A C13A 105.5(7) . . ?
C10A N14A Pr1 116.5(5) . . ?
C13A N14A Pr1 137.4(5) . . ?
C6B N1B C2B 118.1(7) . . ?
C6B N1B Pr1 116.7(5) . . ?
C2B N1B Pr1 125.2(5) . . ?
N1B C2B N7B 117.3(6) . . ?
N1B C2B C3B 121.7(7) . . ?
N7B C2B C3B 121.0(7) . . ?
C4B C3B C2B 118.0(8) . . ?
C4B C3B H3B 121.0 . . ?
C2B C3B H3B 121.0 . . ?
C3B C4B C5B 121.0(8) . . ?
C3B C4B H4B 119.5 . . ?
C5B C4B H4B 119.5 . . ?
C6B C5B C4B 117.4(8) . . ?
C6B C5B H5B 121.3 . . ?
C4B C5B H5B 121.3 . . ?
N1B C6B C5B 123.9(8) . . ?
N1B C6B H6B 118.1 . . ?
C5B C6B H6B 118.1 . . ?
N8B N7B C2B 116.3(6) . . ?
N8B N7B C71B 119.7(6) . . ?
C2B N7B C71B 124.0(6) . . ?
N7B C71B H71F 109.5 . . ?
N7B C71B H71E 109.5 . . ?
H71F C71B H71E 109.5 . . ?
N7B C71B H71D 109.5 . . ?
H71F C71B H71D 109.5 . . ?
H71E C71B H71D 109.5 . . ?
C9B N8B N7B 120.3(6) . . ?
C9B N8B Pr1 118.1(5) . . ?
N7B N8B Pr1 121.5(4) . . ?
N8B C9B C10B 116.0(7) . . ?
N8B C9B H9B 122.0 . . ?
C10B C9B H9B 122.0 . . ?
N14B C10B N11B 110.2(6) . . ?
N14B C10B C9B 123.6(6) . . ?
N11B C10B C9B 126.3(7) . . ?
C10B N11B C12B 107.4(6) . . ?
C10B N11B C11B 127.8(6) . . ?
C12B N11B C11B 124.7(6) . . ?
N11B C11B H11F 109.5 . . ?
N11B C11B H11E 109.5 . . ?
H11F C11B H11E 109.5 . . ?
N11B C11B H11D 109.5 . . ?
H11F C11B H11D 109.5 . . ?
H11E C11B H11D 109.5 . . ?
C13B C12B N11B 106.8(6) . . ?
C13B C12B H12B 126.6 . . ?
N11B C12B H12B 126.6 . . ?
C12B C13B N14B 109.7(7) . . ?
C12B C13B H13B 125.1 . . ?
N14B C13B H13B 125.1 . . ?
C10B N14B C13B 106.0(5) . . ?
C10B N14B Pr1 118.0(4) . . ?
C13B N14B Pr1 134.6(5) . . ?
O11C S1C O12C 116.4(4) . . ?
O11C S1C O13C 113.8(3) . . ?
O12C S1C O13C 114.9(3) . . ?
O11C S1C C1C 102.8(4) . . ?
O12C S1C C1C 103.4(4) . . ?
O13C S1C C1C 103.1(4) . . ?
S1C O13C Pr1 168.0(3) . . ?
F11C C1C F12C 107.3(7) . . ?
F11C C1C F13C 107.8(7) . . ?
F12C C1C F13C 107.4(9) . . ?
F11C C1C S1C 111.6(7) . . ?
F12C C1C S1C 111.8(6) . . ?
F13C C1C S1C 110.8(6) . . ?
O12D S1D O11D 117.0(4) . . ?
O12D S1D O13D 114.0(4) . . ?
O11D S1D O13D 114.0(4) . . ?
O12D S1D C1D 102.8(3) . . ?
O11D S1D C1D 103.6(4) . . ?
O13D S1D C1D 102.9(3) . . ?
S1D O13D Pr1 144.4(3) . . ?
F11D C1D F13D 107.4(6) . . ?
F11D C1D F12D 108.6(7) . . ?
F13D C1D F12D 105.9(6) . . ?
F11D C1D S1D 110.8(5) . . ?
F13D C1D S1D 112.0(5) . . ?
F12D C1D S1D 111.9(5) . . ?
O11E S1E O12E 117.1(3) . . ?
O11E S1E O13E 114.0(3) . . ?
O12E S1E O13E 113.9(3) . . ?
O11E S1E C1E 104.0(3) . . ?
O12E S1E C1E 103.0(4) . . ?
O13E S1E C1E 102.4(3) . . ?
S1E O13E Pr1 142.0(3) . . ?
F12E C1E F11E 108.4(6) . . ?
F12E C1E F13E 108.8(7) . . ?
F11E C1E F13E 107.0(6) . . ?
F12E C1E S1E 110.7(5) . . ?
F11E C1E S1E 111.2(6) . . ?
F13E C1E S1E 110.6(5) . . ?
N1F C2F C3F 177.6(12) . . ?
C2F C3F H3F3 109.5 . . ?
C2F C3F H3F2 109.5 . . ?
H3F3 C3F H3F2 109.5 . . ?
C2F C3F H3F1 109.5 . . ?
H3F3 C3F H3F1 109.5 . . ?
H3F2 C3F H3F1 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6A N1A C2A N7A 178.9(6) . . . . ?
Pr1 N1A C2A N7A -4.6(8) . . . . ?
C6A N1A C2A C3A 0.5(10) . . . . ?
Pr1 N1A C2A C3A 177.1(5) . . . . ?
N1A C2A C3A C4A -0.5(12) . . . . ?
N7A C2A C3A C4A -178.7(7) . . . . ?
C2A C3A C4A C5A 0.9(12) . . . . ?
C3A C4A C5A C6A -1.4(12) . . . . ?
C2A N1A C6A C5A -1.0(11) . . . . ?
Pr1 N1A C6A C5A -177.8(6) . . . . ?
C4A C5A C6A N1A 1.4(12) . . . . ?
N1A C2A N7A N8A -13.1(9) . . . . ?
C3A C2A N7A N8A 165.2(7) . . . . ?
N1A C2A N7A C71A 174.7(7) . . . . ?
C3A C2A N7A C71A -6.9(11) . . . . ?
C2A N7A N8A C9A -168.0(6) . . . . ?
C71A N7A N8A C9A 4.2(10) . . . . ?
C2A N7A N8A Pr1 24.3(8) . . . . ?
C71A N7A N8A Pr1 -163.4(5) . . . . ?
N7A N8A C9A C10A -176.1(6) . . . . ?
Pr1 N8A C9A C10A -8.3(9) . . . . ?
N8A C9A C10A N14A -0.1(12) . . . . ?
N8A C9A C10A N11A -180.0(7) . . . . ?
N14A C10A N11A C12A -1.2(9) . . . . ?
C9A C10A N11A C12A 178.7(8) . . . . ?
N14A C10A N11A C11A 174.6(8) . . . . ?
C9A C10A N11A C11A -5.5(13) . . . . ?
C10A N11A C12A C13A 0.9(9) . . . . ?
C11A N11A C12A C13A -175.0(8) . . . . ?
N11A C12A C13A N14A -0.3(9) . . . . ?
N11A C10A N14A C13A 1.0(9) . . . . ?
C9A C10A N14A C13A -178.9(8) . . . . ?
N11A C10A N14A Pr1 -171.5(5) . . . . ?
C9A C10A N14A Pr1 8.6(10) . . . . ?
C12A C13A N14A C10A -0.4(9) . . . . ?
C12A C13A N14A Pr1 169.6(5) . . . . ?
C6B N1B C2B N7B -179.8(7) . . . . ?
Pr1 N1B C2B N7B 1.3(9) . . . . ?
C6B N1B C2B C3B -0.2(11) . . . . ?
Pr1 N1B C2B C3B -179.0(6) . . . . ?
N1B C2B C3B C4B 0.1(13) . . . . ?
N7B C2B C3B C4B 179.7(8) . . . . ?
C2B C3B C4B C5B 0.4(14) . . . . ?
C3B C4B C5B C6B -0.7(14) . . . . ?
C2B N1B C6B C5B -0.2(11) . . . . ?
Pr1 N1B C6B C5B 178.7(6) . . . . ?
C4B C5B C6B N1B 0.6(12) . . . . ?
N1B C2B N7B N8B -0.3(9) . . . . ?
C3B C2B N7B N8B 180.0(7) . . . . ?
N1B C2B N7B C71B 177.4(7) . . . . ?
C3B C2B N7B C71B -2.2(12) . . . . ?
C2B N7B N8B C9B 177.2(6) . . . . ?
C71B N7B N8B C9B -0.7(10) . . . . ?
C2B N7B N8B Pr1 -0.7(8) . . . . ?
C71B N7B N8B Pr1 -178.6(5) . . . . ?
N7B N8B C9B C10B 179.9(6) . . . . ?
Pr1 N8B C9B C10B -2.1(8) . . . . ?
N8B C9B C10B N14B -5.8(11) . . . . ?
N8B C9B C10B N11B 172.5(7) . . . . ?
N14B C10B N11B C12B -0.3(8) . . . . ?
C9B C10B N11B C12B -178.8(7) . . . . ?
N14B C10B N11B C11B 176.3(7) . . . . ?
C9B C10B N11B C11B -2.2(12) . . . . ?
C10B N11B C12B C13B 0.1(8) . . . . ?
C11B N11B C12B C13B -176.6(7) . . . . ?
N11B C12B C13B N14B 0.1(9) . . . . ?
N11B C10B N14B C13B 0.4(8) . . . . ?
C9B C10B N14B C13B 178.9(7) . . . . ?
N11B C10B N14B Pr1 -167.6(5) . . . . ?
C9B C10B N14B Pr1 10.9(9) . . . . ?
C12B C13B N14B C10B -0.3(9) . . . . ?
C12B C13B N14B Pr1 164.8(5) . . . . ?
O11C S1C O13C Pr1 -91.7(16) . . . . ?
O12C S1C O13C Pr1 46.1(17) . . . . ?
C1C S1C O13C Pr1 157.7(16) . . . . ?
O11C S1C C1C F11C 60.2(7) . . . . ?
O12C S1C C1C F11C -61.3(7) . . . . ?
O13C S1C C1C F11C 178.8(6) . . . . ?
O11C S1C C1C F12C -179.5(5) . . . . ?
O12C S1C C1C F12C 58.9(6) . . . . ?
O13C S1C C1C F12C -61.0(6) . . . . ?
O11C S1C C1C F13C -59.8(7) . . . . ?
O12C S1C C1C F13C 178.6(7) . . . . ?
O13C S1C C1C F13C 58.7(7) . . . . ?
O12D S1D O13D Pr1 -88.7(7) . . . . ?
O11D S1D O13D Pr1 49.2(7) . . . . ?
C1D S1D O13D Pr1 160.7(6) . . . . ?
O12D S1D C1D F11D 65.0(7) . . . . ?
O11D S1D C1D F11D -57.3(7) . . . . ?
O13D S1D C1D F11D -176.3(6) . . . . ?
O12D S1D C1D F13D -175.2(6) . . . . ?
O11D S1D C1D F13D 62.6(6) . . . . ?
O13D S1D C1D F13D -56.5(7) . . . . ?
O12D S1D C1D F12D -56.4(6) . . . . ?
O11D S1D C1D F12D -178.6(5) . . . . ?
O13D S1D C1D F12D 62.3(6) . . . . ?
O11E S1E O13E Pr1 103.1(5) . . . . ?
O12E S1E O13E Pr1 -34.8(7) . . . . ?
C1E S1E O13E Pr1 -145.3(5) . . . . ?
O11E S1E C1E F12E -64.6(6) . . . . ?
O12E S1E C1E F12E 58.1(6) . . . . ?
O13E S1E C1E F12E 176.5(5) . . . . ?
O11E S1E C1E F11E 55.9(6) . . . . ?
O12E S1E C1E F11E 178.6(5) . . . . ?
O13E S1E C1E F11E -63.0(6) . . . . ?
O11E S1E C1E F13E 174.7(5) . . . . ?
O12E S1E C1E F13E -62.7(6) . . . . ?
O13E S1E C1E F13E 55.8(6) . . . . ?

_refine_diff_density_max         2.419
_refine_diff_density_min         -1.067
_refine_diff_density_rms         0.123

_shelxl_version_number           2013-4

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_15
_database_code_depnum_ccdc_archive 'CCDC 1435582'
_audit_update_record             
;
2015-11-06 deposited with the CCDC.	2024-07-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C11 H15 N8 O10 Sm, C H4 O'
_chemical_formula_sum            'C12 H19 N8 O11 Sm'
_chemical_formula_weight         601.70

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Sm Sm -0.1638 3.4418 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.1537(3)
_cell_length_b                   10.4239(4)
_cell_length_c                   12.3673(3)
_cell_angle_alpha                96.710(3)
_cell_angle_beta                 98.034(3)
_cell_angle_gamma                100.381(4)
_cell_volume                     1012.84(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    120(1)
_cell_measurement_reflns_used    3914
_cell_measurement_theta_min      3.3150
_cell_measurement_theta_max      28.0120

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.973
_exptl_crystal_F_000             594
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.04
_exptl_absorpt_coefficient_mu    2.975
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.68040
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?

_diffrn_ambient_temperature      120(1)
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Eos
_diffrn_detector_area_resol_mean 16.1544
_diffrn_measurement_method       ω-scan
_diffrn_reflns_number            7077
_diffrn_reflns_av_unetI/netI     0.0335
_diffrn_reflns_av_R_equivalents  0.0199
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.801
_diffrn_reflns_theta_max         28.219
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.837
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.837
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.837
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4169
_reflns_number_gt                3879
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlis Pro (Agilent Technologies (2011))'
_computing_cell_refinement       'CrysAlis Pro (Agilent Technologies (2011))'
_computing_data_reduction        'CrysAlis Pro (Agilent Technologies (2011))'
_computing_structure_solution    'SIR92 (Altomare et al., 1993)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Mercury (MacRae et al., 2009)'
_computing_publication_material  'SHELXL-2013 (Sheldrick, 2013)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0195P)²+0.3697P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4169
_refine_ls_number_parameters     304
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0239
_refine_ls_R_factor_gt           0.0207
_refine_ls_wR_factor_ref         0.0462
_refine_ls_wR_factor_gt          0.0451
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.042
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Sm1 Sm 0.30021(2) 0.77288(2) 0.28739(2) 0.00973(5) Uani 1 1 d . . . . .
N1A N 0.0447(3) 0.6962(2) 0.37892(17) 0.0114(4) Uani 1 1 d . . . . .
C2A C -0.0194(3) 0.7843(3) 0.4410(2) 0.0156(6) Uani 1 1 d . . . . .
H2A H 0.0351 0.8744 0.4507 0.019 Uiso 1 1 calc R U . . .
C3A C -0.1580(3) 0.7520(3) 0.4910(2) 0.0181(6) Uani 1 1 d . . . . .
H3A H -0.1988 0.8176 0.5336 0.022 Uiso 1 1 calc R U . . .
C4A C -0.2367(3) 0.6199(3) 0.4772(2) 0.0175(6) Uani 1 1 d . . . . .
H4A H -0.3316 0.5934 0.5119 0.021 Uiso 1 1 calc R U . . .
C5A C -0.1768(3) 0.5283(3) 0.4134(2) 0.0148(5) Uani 1 1 d . . . . .
H5A H -0.2301 0.4378 0.4030 0.018 Uiso 1 1 calc R U . . .
C6A C -0.0362(3) 0.5695(2) 0.3638(2) 0.0118(5) Uani 1 1 d . . . . .
N7A N 0.0272(3) 0.4799(2) 0.29694(18) 0.0130(5) Uani 1 1 d . . . . .
C71A C -0.0556(3) 0.3417(2) 0.2669(2) 0.0169(6) Uani 1 1 d . . . . .
H71C H -0.0454 0.3113 0.1906 0.025 Uiso 1 1 calc R U . . .
H71B H -0.1754 0.3319 0.2737 0.025 Uiso 1 1 calc R U . . .
H71A H -0.0017 0.2889 0.3164 0.025 Uiso 1 1 calc R U . . .
N8A N 0.1806(3) 0.5241(2) 0.26833(17) 0.0110(4) Uani 1 1 d . . . . .
C9A C 0.2637(3) 0.4428(3) 0.2252(2) 0.0132(5) Uani 1 1 d . . . . .
H9A H 0.2221 0.3503 0.2128 0.016 Uiso 1 1 calc R U . . .
C10A C 0.4236(3) 0.5009(3) 0.1970(2) 0.0126(5) Uani 1 1 d . . . . .
N11A N 0.5222(3) 0.4346(2) 0.14134(17) 0.0131(5) Uani 1 1 d . . . . .
C11A C 0.4873(4) 0.2935(3) 0.1002(2) 0.0196(6) Uani 1 1 d . . . . .
H11C H 0.5002 0.2440 0.1625 0.029 Uiso 1 1 calc R U . . .
H11B H 0.5669 0.2750 0.0507 0.029 Uiso 1 1 calc R U . . .
H11A H 0.3715 0.2668 0.0598 0.029 Uiso 1 1 calc R U . . .
C12A C 0.6601(3) 0.5260(3) 0.1290(2) 0.0154(6) Uani 1 1 d . . . . .
H12A H 0.7513 0.5096 0.0928 0.018 Uiso 1 1 calc R U . . .
C13A C 0.6404(3) 0.6443(3) 0.1785(2) 0.0156(6) Uani 1 1 d . . . . .
H13A H 0.7174 0.7256 0.1830 0.019 Uiso 1 1 calc R U . . .
N14A N 0.4932(3) 0.6290(2) 0.22104(17) 0.0129(5) Uani 1 1 d . . . . .
N1B N 0.2255(3) 1.0230(2) 0.2221(2) 0.0202(5) Uani 1 1 d . . . . .
O11B O 0.1908(3) 0.98204(18) 0.31086(17) 0.0235(5) Uani 1 1 d . . . . .
O12B O 0.3142(2) 0.96051(18) 0.16838(16) 0.0199(4) Uani 1 1 d . . . . .
O13B O 0.1708(3) 1.1160(2) 0.1898(2) 0.0343(5) Uani 1 1 d . . . . .
N1C N 0.0704(3) 0.6970(2) 0.07199(18) 0.0194(5) Uani 1 1 d . . . . .
O11C O 0.0260(2) 0.7469(2) 0.15888(15) 0.0200(4) Uani 1 1 d . . . . .
O12C O 0.2227(2) 0.68360(18) 0.07974(15) 0.0178(4) Uani 1 1 d . . . . .
O13C O -0.0295(3) 0.6629(3) -0.01463(17) 0.0401(6) Uani 1 1 d . . . . .
N1D N 0.4122(3) 0.7770(2) 0.52805(18) 0.0160(5) Uani 1 1 d . . . . .
O11D O 0.3657(2) 0.87739(17) 0.49203(15) 0.0165(4) Uani 1 1 d . . . . .
O12D O 0.4064(2) 0.67870(17) 0.45673(15) 0.0159(4) Uani 1 1 d . . . . .
O13D O 0.4601(3) 0.7770(2) 0.62658(16) 0.0293(5) Uani 1 1 d . . . . .
O1E O 0.5794(3) 0.9108(2) 0.33678(19) 0.0173(4) Uani 1 1 d . . . . .
H2E H 0.640(4) 0.940(3) 0.295(3) 0.024(9) Uiso 1 1 d . . . . .
H1E H 0.593(4) 0.964(3) 0.384(3) 0.019(9) Uiso 1 1 d . . . . .
O1F O 0.8043(3) 1.0042(3) 0.2119(2) 0.0435(7) Uani 1 1 d . . . . .
H1F H 0.925(10) 1.023(8) 0.243(7) 0.21(4) Uiso 1 1 d . . . . .
C1F C 0.7682(5) 1.0049(4) 0.0954(3) 0.0449(10) Uani 1 1 d . . . . .
H1F3 H 0.8239 1.0895 0.0776 0.067 Uiso 1 1 calc R U . . .
H1F2 H 0.6458 0.9927 0.0721 0.067 Uiso 1 1 calc R U . . .
H1F1 H 0.8102 0.9332 0.0567 0.067 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Sm1 O1E 2.4184(19) . ?
Sm1 O11B 2.5017(19) . ?
Sm1 O11C 2.5069(19) . ?
Sm1 N14A 2.515(2) . ?
Sm1 O12D 2.5258(19) . ?
Sm1 N1A 2.555(2) . ?
Sm1 N8A 2.572(2) . ?
Sm1 O12C 2.5761(18) . ?
Sm1 O12B 2.578(2) . ?
Sm1 O11D 2.5778(17) . ?
Sm1 N1B 2.958(2) . ?
Sm1 N1C 2.969(2) . ?
N1A C6A 1.345(3) . ?
N1A C2A 1.351(3) . ?
C2A C3A 1.371(4) . ?
C2A H2A 0.9500 . ?
C3A C4A 1.390(4) . ?
C3A H3A 0.9500 . ?
C4A C5A 1.368(4) . ?
C4A H4A 0.9500 . ?
C5A C6A 1.399(4) . ?
C5A H5A 0.9500 . ?
C6A N7A 1.392(3) . ?
N7A N8A 1.362(3) . ?
N7A C71A 1.458(3) . ?
C71A H71C 0.9800 . ?
C71A H71B 0.9800 . ?
C71A H71A 0.9800 . ?
N8A C9A 1.290(3) . ?
C9A C10A 1.442(4) . ?
C9A H9A 0.9500 . ?
C10A N14A 1.334(3) . ?
C10A N11A 1.357(3) . ?
N11A C12A 1.375(3) . ?
N11A C11A 1.463(3) . ?
C11A H11C 0.9800 . ?
C11A H11B 0.9800 . ?
C11A H11A 0.9800 . ?
C12A C13A 1.359(4) . ?
C12A H12A 0.9500 . ?
C13A N14A 1.367(3) . ?
C13A H13A 0.9500 . ?
N1B O13B 1.223(3) . ?
N1B O12B 1.262(3) . ?
N1B O11B 1.273(3) . ?
N1C O13C 1.225(3) . ?
N1C O11C 1.266(3) . ?
N1C O12C 1.266(3) . ?
N1D O13D 1.226(3) . ?
N1D O12D 1.261(3) . ?
N1D O11D 1.282(3) . ?
O1E H2E 0.81(4) . ?
O1E H1E 0.74(3) . ?
O1F C1F 1.431(4) . ?
O1F H1F 0.98(8) . ?
C1F H1F3 0.9800 . ?
C1F H1F2 0.9800 . ?
C1F H1F1 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1E Sm1 O11B 86.24(7) . . ?
O1E Sm1 O11C 141.98(7) . . ?
O11B Sm1 O11C 70.59(7) . . ?
O1E Sm1 N14A 75.68(7) . . ?
O11B Sm1 N14A 154.49(7) . . ?
O11C Sm1 N14A 113.82(6) . . ?
O1E Sm1 O12D 80.61(7) . . ?
O11B Sm1 O12D 119.15(6) . . ?
O11C Sm1 O12D 136.87(6) . . ?
N14A Sm1 O12D 75.95(6) . . ?
O1E Sm1 N1A 138.77(7) . . ?
O11B Sm1 N1A 80.10(7) . . ?
O11C Sm1 N1A 67.72(6) . . ?
N14A Sm1 N1A 125.27(7) . . ?
O12D Sm1 N1A 72.83(6) . . ?
O1E Sm1 N8A 134.93(7) . . ?
O11B Sm1 N8A 137.30(7) . . ?
O11C Sm1 N8A 77.59(7) . . ?
N14A Sm1 N8A 65.61(7) . . ?
O12D Sm1 N8A 68.68(6) . . ?
N1A Sm1 N8A 61.56(7) . . ?
O1E Sm1 O12C 112.97(7) . . ?
O11B Sm1 O12C 105.48(6) . . ?
O11C Sm1 O12C 50.08(6) . . ?
N14A Sm1 O12C 66.78(6) . . ?
O12D Sm1 O12C 134.36(6) . . ?
N1A Sm1 O12C 108.15(6) . . ?
N8A Sm1 O12C 72.41(6) . . ?
O1E Sm1 O12B 72.19(7) . . ?
O11B Sm1 O12B 50.23(6) . . ?
O11C Sm1 O12B 69.82(6) . . ?
N14A Sm1 O12B 106.16(7) . . ?
O12D Sm1 O12B 150.94(6) . . ?
N1A Sm1 O12B 122.71(6) . . ?
N8A Sm1 O12B 139.34(6) . . ?
O12C Sm1 O12B 68.19(6) . . ?
O1E Sm1 O11D 67.47(7) . . ?
O11B Sm1 O11D 69.95(6) . . ?
O11C Sm1 O11D 126.61(6) . . ?
N14A Sm1 O11D 117.39(7) . . ?
O12D Sm1 O11D 50.08(6) . . ?
N1A Sm1 O11D 71.30(6) . . ?
N8A Sm1 O11D 110.69(6) . . ?
O12C Sm1 O11D 175.43(6) . . ?
O12B Sm1 O11D 108.11(6) . . ?
O1E Sm1 N1B 80.23(7) . . ?
O11B Sm1 N1B 25.24(6) . . ?
O11C Sm1 N1B 65.87(6) . . ?
N14A Sm1 N1B 131.16(7) . . ?
O12D Sm1 N1B 140.30(6) . . ?
N1A Sm1 N1B 100.65(7) . . ?
N8A Sm1 N1B 143.40(7) . . ?
O12C Sm1 N1B 85.24(6) . . ?
O12B Sm1 N1B 25.17(6) . . ?
O11D Sm1 N1B 90.40(6) . . ?
O1E Sm1 N1C 131.00(7) . . ?
O11B Sm1 N1C 88.21(7) . . ?
O11C Sm1 N1C 24.95(6) . . ?
N14A Sm1 N1C 90.23(7) . . ?
O12D Sm1 N1C 141.58(6) . . ?
N1A Sm1 N1C 87.50(6) . . ?
N8A Sm1 N1C 72.94(7) . . ?
O12C Sm1 N1C 25.14(6) . . ?
O12B Sm1 N1C 67.20(6) . . ?
O11D Sm1 N1C 151.51(7) . . ?
N1B Sm1 N1C 74.66(6) . . ?
C6A N1A C2A 117.2(2) . . ?
C6A N1A Sm1 122.28(16) . . ?
C2A N1A Sm1 120.47(16) . . ?
N1A C2A C3A 124.3(3) . . ?
N1A C2A H2A 117.9 . . ?
C3A C2A H2A 117.9 . . ?
C2A C3A C4A 117.6(2) . . ?
C2A C3A H3A 121.2 . . ?
C4A C3A H3A 121.2 . . ?
C5A C4A C3A 119.7(2) . . ?
C5A C4A H4A 120.1 . . ?
C3A C4A H4A 120.1 . . ?
C4A C5A C6A 119.1(2) . . ?
C4A C5A H5A 120.4 . . ?
C6A C5A H5A 120.4 . . ?
N1A C6A N7A 116.9(2) . . ?
N1A C6A C5A 122.0(2) . . ?
N7A C6A C5A 121.0(2) . . ?
N8A N7A C6A 116.74(19) . . ?
N8A N7A C71A 120.4(2) . . ?
C6A N7A C71A 122.6(2) . . ?
N7A C71A H71C 109.5 . . ?
N7A C71A H71B 109.5 . . ?
H71C C71A H71B 109.5 . . ?
N7A C71A H71A 109.5 . . ?
H71C C71A H71A 109.5 . . ?
H71B C71A H71A 109.5 . . ?
C9A N8A N7A 120.9(2) . . ?
C9A N8A Sm1 118.72(16) . . ?
N7A N8A Sm1 120.28(15) . . ?
N8A C9A C10A 116.0(2) . . ?
N8A C9A H9A 122.0 . . ?
C10A C9A H9A 122.0 . . ?
N14A C10A N11A 110.7(2) . . ?
N14A C10A C9A 124.0(2) . . ?
N11A C10A C9A 125.3(2) . . ?
C10A N11A C12A 106.9(2) . . ?
C10A N11A C11A 126.7(2) . . ?
C12A N11A C11A 126.4(2) . . ?
N11A C11A H11C 109.5 . . ?
N11A C11A H11B 109.5 . . ?
H11C C11A H11B 109.5 . . ?
N11A C11A H11A 109.5 . . ?
H11C C11A H11A 109.5 . . ?
H11B C11A H11A 109.5 . . ?
C13A C12A N11A 106.5(2) . . ?
C13A C12A H12A 126.7 . . ?
N11A C12A H12A 126.7 . . ?
C12A C13A N14A 109.8(2) . . ?
C12A C13A H13A 125.1 . . ?
N14A C13A H13A 125.1 . . ?
C10A N14A C13A 106.0(2) . . ?
C10A N14A Sm1 114.62(16) . . ?
C13A N14A Sm1 137.49(17) . . ?
O13B N1B O12B 122.3(3) . . ?
O13B N1B O11B 121.1(2) . . ?
O12B N1B O11B 116.6(2) . . ?
O13B N1B Sm1 170.54(19) . . ?
O12B N1B Sm1 60.32(13) . . ?
O11B N1B Sm1 56.92(13) . . ?
N1B O11B Sm1 97.84(15) . . ?
N1B O12B Sm1 94.51(15) . . ?
O13C N1C O11C 121.5(2) . . ?
O13C N1C O12C 122.0(2) . . ?
O11C N1C O12C 116.4(2) . . ?
O13C N1C Sm1 177.29(19) . . ?
O11C N1C Sm1 56.66(12) . . ?
O12C N1C Sm1 59.82(12) . . ?
N1C O11C Sm1 98.39(15) . . ?
N1C O12C Sm1 95.04(14) . . ?
O13D N1D O12D 122.0(2) . . ?
O13D N1D O11D 121.6(2) . . ?
O12D N1D O11D 116.4(2) . . ?
O13D N1D Sm1 178.8(2) . . ?
O12D N1D Sm1 56.95(12) . . ?
O11D N1D Sm1 59.42(12) . . ?
N1D O11D Sm1 95.23(13) . . ?
N1D O12D Sm1 98.32(15) . . ?
Sm1 O1E H2E 127(2) . . ?
Sm1 O1E H1E 117(2) . . ?
H2E O1E H1E 105(3) . . ?
C1F O1F H1F 114(5) . . ?
O1F C1F H1F3 109.5 . . ?
O1F C1F H1F2 109.5 . . ?
H1F3 C1F H1F2 109.5 . . ?
O1F C1F H1F1 109.5 . . ?
H1F3 C1F H1F1 109.5 . . ?
H1F2 C1F H1F1 109.5 . . ?

_refine_diff_density_max         0.619
_refine_diff_density_min         -0.497
_refine_diff_density_rms         0.095

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_20
_database_code_depnum_ccdc_archive 'CCDC 1052301'
_audit_update_record             
;
2016-01-10 deposited with the CCDC.	2024-07-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H17 Ho N8 O10, C2 H3 N'
_chemical_formula_sum            'C14 H20 Ho N9 O10'
_chemical_formula_weight         639.32

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ho Ho -0.2175 4.6783 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.2808(4)
_cell_length_b                   11.2432(6)
_cell_length_c                   13.2986(9)
_cell_angle_alpha                68.357(6)
_cell_angle_beta                 72.061(5)
_cell_angle_gamma                87.716(4)
_cell_volume                     1091.08(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(1)
_cell_measurement_reflns_used    4399
_cell_measurement_theta_min      3.5420
_cell_measurement_theta_max      28.0750

_exptl_crystal_description       plate
_exptl_crystal_colour            pale-yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.946
_exptl_crystal_F_000             628
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.05
_exptl_absorpt_coefficient_mu    3.698
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.49731
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           ?

_diffrn_ambient_temperature      100(1)
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Eos
_diffrn_detector_area_resol_mean 16.1544
_diffrn_measurement_method       ω-scan
_diffrn_reflns_number            8017
_diffrn_reflns_av_unetI/netI     0.0380
_diffrn_reflns_av_R_equivalents  0.0262
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.004
_diffrn_reflns_theta_max         28.387
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.830
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.830
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.830
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4528
_reflns_number_gt                4302
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlis Pro (Agilent Technologies (2011))'
_computing_cell_refinement       'CrysAlis Pro (Agilent Technologies (2011))'
_computing_data_reduction        'CrysAlis Pro (Agilent Technologies (2011))'
_computing_structure_solution    'SIR92 (Altomare et al., 1993)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Mercury (MacRae et al., 2009)'
_computing_publication_material  'SHELXL-2013 (Sheldrick, 2013)'

_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0322P)²+0.8927P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4528
_refine_ls_number_parameters     315
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0284
_refine_ls_R_factor_gt           0.0264
_refine_ls_wR_factor_ref         0.0656
_refine_ls_wR_factor_gt          0.0641
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_restrained_S_all      1.086
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Ho1 Ho 0.43326(2) 0.34348(2) 0.25674(2) 0.01223(6) Uani 1 1 d . . . . .
N1A N 0.6504(3) 0.4396(3) 0.3091(2) 0.0146(6) Uani 1 1 d . . . . .
C2A C 0.7889(4) 0.5140(4) 0.2282(3) 0.0180(7) Uani 1 1 d . . . . .
H2A H 0.7972 0.5367 0.1504 0.022 Uiso 1 1 calc R U . . .
C3A C 0.9180(4) 0.5583(4) 0.2529(3) 0.0229(8) Uani 1 1 d . . . . .
H3A H 1.0151 0.6083 0.1935 0.028 Uiso 1 1 calc R U . . .
C4A C 0.9040(4) 0.5285(4) 0.3663(3) 0.0199(8) Uani 1 1 d . . . . .
H4A H 0.9902 0.5604 0.3855 0.024 Uiso 1 1 calc R U . . .
C5A C 0.7653(4) 0.4530(4) 0.4507(3) 0.0169(7) Uani 1 1 d . . . . .
H5A H 0.7536 0.4325 0.5288 0.020 Uiso 1 1 calc R U . . .
C6A C 0.6413(4) 0.4066(3) 0.4194(3) 0.0149(7) Uani 1 1 d . . . . .
N7A N 0.5031(4) 0.3264(3) 0.5009(2) 0.0156(6) Uani 1 1 d . . . . .
C71A C 0.4849(4) 0.2737(4) 0.6223(3) 0.0182(7) Uani 1 1 d . . . . .
H71A H 0.4030 0.3205 0.6611 0.027 Uiso 1 1 calc R U . . .
H71B H 0.5956 0.2825 0.6324 0.027 Uiso 1 1 calc R U . . .
H71C H 0.4439 0.1827 0.6548 0.027 Uiso 1 1 calc R U . . .
N8A N 0.3792(3) 0.2994(3) 0.4633(2) 0.0134(6) Uani 1 1 d . . . . .
C9A C 0.2358(4) 0.2400(3) 0.5370(3) 0.0155(7) Uani 1 1 d . . . . .
H9A H 0.2135 0.2136 0.6169 0.019 Uiso 1 1 calc R U . . .
C10A C 0.1127(4) 0.2171(3) 0.4878(3) 0.0143(7) Uani 1 1 d . . . . .
N11A N -0.0394(4) 0.1471(3) 0.5483(3) 0.0161(6) Uani 1 1 d . . . . .
C11A C -0.1072(5) 0.0823(4) 0.6717(3) 0.0209(8) Uani 1 1 d . . . . .
H11C H -0.0160 0.0411 0.7013 0.031 Uiso 1 1 calc R U . . .
H11B H -0.1984 0.0171 0.6908 0.031 Uiso 1 1 calc R U . . .
H11A H -0.1527 0.1452 0.7060 0.031 Uiso 1 1 calc R U . . .
C12A C -0.1155(4) 0.1459(4) 0.4703(3) 0.0173(7) Uani 1 1 d . . . . .
H12A H -0.2232 0.1043 0.4864 0.021 Uiso 1 1 calc R U . . .
C13A C -0.0060(4) 0.2160(3) 0.3653(3) 0.0168(7) Uani 1 1 d . . . . .
H13A H -0.0260 0.2317 0.2951 0.020 Uiso 1 1 calc R U . . .
N14A N 0.1373(3) 0.2604(3) 0.3762(3) 0.0155(6) Uani 1 1 d . . . . .
N1B N 0.2538(4) 0.3155(3) 0.1075(3) 0.0220(7) Uani 1 1 d . . . . .
O11B O 0.1641(4) 0.3066(3) 0.0529(2) 0.0338(7) Uani 1 1 d . . . . .
O12B O 0.3257(3) 0.2222(3) 0.1591(2) 0.0236(6) Uani 1 1 d . . . . .
O13B O 0.2801(3) 0.4220(3) 0.1165(2) 0.0204(6) Uani 1 1 d . . . . .
N1C N 0.5605(4) 0.0965(3) 0.3513(3) 0.0182(6) Uani 1 1 d . . . . .
O11C O 0.6190(4) -0.0059(3) 0.3916(3) 0.0320(7) Uani 1 1 d . . . . .
O12C O 0.6509(3) 0.2020(2) 0.3089(2) 0.0197(6) Uani 1 1 d . . . . .
O13C O 0.4099(3) 0.1037(3) 0.3492(2) 0.0242(6) Uani 1 1 d . . . . .
N1D N 0.3885(4) 0.6149(3) 0.1990(3) 0.0174(6) Uani 1 1 d . . . . .
O11D O 0.3609(4) 0.7281(3) 0.1786(2) 0.0272(6) Uani 1 1 d . . . . .
O12D O 0.3048(3) 0.5268(2) 0.2934(2) 0.0174(5) Uani 1 1 d . . . . .
O13D O 0.4996(3) 0.5787(2) 0.1295(2) 0.0180(5) Uani 1 1 d . . . . .
O1E O 0.6581(3) 0.3706(3) 0.0880(2) 0.0190(5) Uani 1 1 d . . . . .
H1E H 0.672(7) 0.429(5) 0.028(5) 0.044(16) Uiso 1 1 d . . . . .
C1E C 0.7536(6) 0.2747(5) 0.0536(4) 0.0346(10) Uani 1 1 d . . . . .
H1E1 H 0.7299 0.1927 0.1188 0.052 Uiso 1 1 calc R U . . .
H1E2 H 0.8756 0.3016 0.0261 0.052 Uiso 1 1 calc R U . . .
H1E3 H 0.7204 0.2646 -0.0077 0.052 Uiso 1 1 calc R U . . .
N1F N 0.1319(6) 0.1027(5) 0.8414(4) 0.0622(15) Uani 1 1 d . . . . .
C2F C 0.1947(6) 0.0785(5) 0.9098(4) 0.0416(12) Uani 1 1 d . . . . .
C3F C 0.2773(8) 0.0469(6) 0.9972(5) 0.0594(16) Uani 1 1 d . . . . .
H3F1 H 0.2062 0.0684 1.0611 0.089 Uiso 1 1 calc R U . . .
H3F2 H 0.3885 0.0960 0.9652 0.089 Uiso 1 1 calc R U . . .
H3F3 H 0.2929 -0.0452 1.0241 0.089 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ho1 O1E 2.358(3) . ?
Ho1 O12D 2.422(3) . ?
Ho1 O12C 2.447(3) . ?
Ho1 O13B 2.454(2) . ?
Ho1 N14A 2.468(3) . ?
Ho1 N8A 2.499(3) . ?
Ho1 O13C 2.504(3) . ?
Ho1 N1A 2.523(3) . ?
Ho1 O13D 2.530(3) . ?
Ho1 O12B 2.540(3) . ?
Ho1 N1D 2.898(3) . ?
Ho1 N1C 2.900(3) . ?
N1A C2A 1.351(4) . ?
N1A C6A 1.352(5) . ?
C2A C3A 1.370(5) . ?
C2A H2A 0.9500 . ?
C3A C4A 1.387(6) . ?
C3A H3A 0.9500 . ?
C4A C5A 1.371(5) . ?
C4A H4A 0.9500 . ?
C5A C6A 1.403(5) . ?
C5A H5A 0.9500 . ?
C6A N7A 1.377(4) . ?
N7A N8A 1.359(4) . ?
N7A C71A 1.460(4) . ?
C71A H71A 0.9800 . ?
C71A H71B 0.9800 . ?
C71A H71C 0.9800 . ?
N8A C9A 1.296(4) . ?
C9A C10A 1.445(5) . ?
C9A H9A 0.9500 . ?
C10A N14A 1.331(5) . ?
C10A N11A 1.357(4) . ?
N11A C12A 1.373(5) . ?
N11A C11A 1.457(5) . ?
C11A H11C 0.9800 . ?
C11A H11B 0.9800 . ?
C11A H11A 0.9800 . ?
C12A C13A 1.363(5) . ?
C12A H12A 0.9500 . ?
C13A N14A 1.373(4) . ?
C13A H13A 0.9500 . ?
N1B O11B 1.217(4) . ?
N1B O12B 1.263(4) . ?
N1B O13B 1.281(4) . ?
N1C O11C 1.228(4) . ?
N1C O13C 1.255(4) . ?
N1C O12C 1.267(4) . ?
N1D O11D 1.227(4) . ?
N1D O13D 1.262(4) . ?
N1D O12D 1.280(4) . ?
O1E C1E 1.439(5) . ?
O1E H1E 0.80(5) . ?
C1E H1E1 0.9800 . ?
C1E H1E2 0.9800 . ?
C1E H1E3 0.9800 . ?
N1F C2F 1.127(7) . ?
C2F C3F 1.452(7) . ?
C3F H3F1 0.9800 . ?
C3F H3F2 0.9800 . ?
C3F H3F3 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1E Ho1 O12D 121.02(9) . . ?
O1E Ho1 O12C 72.20(9) . . ?
O12D Ho1 O12C 137.32(8) . . ?
O1E Ho1 O13B 79.95(9) . . ?
O12D Ho1 O13B 77.56(8) . . ?
O12C Ho1 O13B 143.53(9) . . ?
O1E Ho1 N14A 148.35(9) . . ?
O12D Ho1 N14A 76.00(9) . . ?
O12C Ho1 N14A 115.01(9) . . ?
O13B Ho1 N14A 78.29(9) . . ?
O1E Ho1 N8A 141.09(9) . . ?
O12D Ho1 N8A 72.61(9) . . ?
O12C Ho1 N8A 75.10(9) . . ?
O13B Ho1 N8A 138.10(9) . . ?
N14A Ho1 N8A 66.51(9) . . ?
O1E Ho1 O13C 99.11(10) . . ?
O12D Ho1 O13C 139.87(9) . . ?
O12C Ho1 O13C 51.18(8) . . ?
O13B Ho1 O13C 113.13(9) . . ?
N14A Ho1 O13C 69.24(9) . . ?
N8A Ho1 O13C 75.54(9) . . ?
O1E Ho1 N1A 84.63(9) . . ?
O12D Ho1 N1A 75.58(9) . . ?
O12C Ho1 N1A 65.01(9) . . ?
O13B Ho1 N1A 135.79(9) . . ?
N14A Ho1 N1A 126.85(9) . . ?
N8A Ho1 N1A 62.52(9) . . ?
O13C Ho1 N1A 110.10(9) . . ?
O1E Ho1 O13D 69.39(9) . . ?
O12D Ho1 O13D 51.67(8) . . ?
O12C Ho1 O13D 123.17(8) . . ?
O13B Ho1 O13D 64.67(8) . . ?
N14A Ho1 O13D 119.82(9) . . ?
N8A Ho1 O13D 114.05(9) . . ?
O13C Ho1 O13D 168.42(9) . . ?
N1A Ho1 O13D 71.12(9) . . ?
O1E Ho1 O12B 74.70(9) . . ?
O12D Ho1 O12B 124.13(9) . . ?
O12C Ho1 O12B 98.13(9) . . ?
O13B Ho1 O12B 51.04(9) . . ?
N14A Ho1 O12B 73.76(9) . . ?
N8A Ho1 O12B 131.03(9) . . ?
O13C Ho1 O12B 64.16(9) . . ?
N1A Ho1 O12B 156.83(9) . . ?
O13D Ho1 O12B 109.94(8) . . ?
O1E Ho1 N1D 95.14(9) . . ?
O12D Ho1 N1D 25.92(8) . . ?
O12C Ho1 N1D 135.83(8) . . ?
O13B Ho1 N1D 68.60(8) . . ?
N14A Ho1 N1D 98.00(9) . . ?
N8A Ho1 N1D 93.79(9) . . ?
O13C Ho1 N1D 165.74(9) . . ?
N1A Ho1 N1D 71.90(9) . . ?
O13D Ho1 N1D 25.75(8) . . ?
O12B Ho1 N1D 119.62(8) . . ?
O1E Ho1 N1C 85.53(9) . . ?
O12D Ho1 N1C 146.04(8) . . ?
O12C Ho1 N1C 25.66(8) . . ?
O13B Ho1 N1C 131.69(8) . . ?
N14A Ho1 N1C 92.02(9) . . ?
N8A Ho1 N1C 73.47(9) . . ?
O13C Ho1 N1C 25.52(8) . . ?
N1A Ho1 N1C 87.46(9) . . ?
O13D Ho1 N1C 147.96(8) . . ?
O12B Ho1 N1C 80.72(9) . . ?
N1D Ho1 N1C 159.15(8) . . ?
C2A N1A C6A 117.8(3) . . ?
C2A N1A Ho1 121.1(2) . . ?
C6A N1A Ho1 120.7(2) . . ?
N1A C2A C3A 123.2(3) . . ?
N1A C2A H2A 118.4 . . ?
C3A C2A H2A 118.4 . . ?
C2A C3A C4A 118.6(3) . . ?
C2A C3A H3A 120.7 . . ?
C4A C3A H3A 120.7 . . ?
C5A C4A C3A 119.8(3) . . ?
C5A C4A H4A 120.1 . . ?
C3A C4A H4A 120.1 . . ?
C4A C5A C6A 118.6(3) . . ?
C4A C5A H5A 120.7 . . ?
C6A C5A H5A 120.7 . . ?
N1A C6A N7A 117.2(3) . . ?
N1A C6A C5A 121.9(3) . . ?
N7A C6A C5A 120.8(3) . . ?
N8A N7A C6A 116.5(3) . . ?
N8A N7A C71A 120.4(3) . . ?
C6A N7A C71A 123.0(3) . . ?
N7A C71A H71A 109.5 . . ?
N7A C71A H71B 109.5 . . ?
H71A C71A H71B 109.5 . . ?
N7A C71A H71C 109.5 . . ?
H71A C71A H71C 109.5 . . ?
H71B C71A H71C 109.5 . . ?
C9A N8A N7A 119.2(3) . . ?
C9A N8A Ho1 119.5(2) . . ?
N7A N8A Ho1 121.1(2) . . ?
N8A C9A C10A 114.6(3) . . ?
N8A C9A H9A 122.7 . . ?
C10A C9A H9A 122.7 . . ?
N14A C10A N11A 111.5(3) . . ?
N14A C10A C9A 123.6(3) . . ?
N11A C10A C9A 124.9(3) . . ?
C10A N11A C12A 106.7(3) . . ?
C10A N11A C11A 126.8(3) . . ?
C12A N11A C11A 126.4(3) . . ?
N11A C11A H11C 109.5 . . ?
N11A C11A H11B 109.5 . . ?
H11C C11A H11B 109.5 . . ?
N11A C11A H11A 109.5 . . ?
H11C C11A H11A 109.5 . . ?
H11B C11A H11A 109.5 . . ?
C13A C12A N11A 106.5(3) . . ?
C13A C12A H12A 126.7 . . ?
N11A C12A H12A 126.7 . . ?
C12A C13A N14A 109.9(3) . . ?
C12A C13A H13A 125.0 . . ?
N14A C13A H13A 125.0 . . ?
C10A N14A C13A 105.4(3) . . ?
C10A N14A Ho1 114.3(2) . . ?
C13A N14A Ho1 138.1(2) . . ?
O11B N1B O12B 123.2(3) . . ?
O11B N1B O13B 121.1(3) . . ?
O12B N1B O13B 115.6(3) . . ?
O11B N1B Ho1 173.2(3) . . ?
O12B N1B Ho1 59.88(17) . . ?
O13B N1B Ho1 56.08(16) . . ?
N1B O12B Ho1 94.6(2) . . ?
N1B O13B Ho1 98.3(2) . . ?
O11C N1C O13C 122.9(3) . . ?
O11C N1C O12C 121.1(3) . . ?
O13C N1C O12C 116.0(3) . . ?
O11C N1C Ho1 177.7(2) . . ?
O13C N1C Ho1 59.29(18) . . ?
O12C N1C Ho1 56.76(17) . . ?
N1C O12C Ho1 97.58(19) . . ?
N1C O13C Ho1 95.2(2) . . ?
O11D N1D O13D 122.6(3) . . ?
O11D N1D O12D 121.1(3) . . ?
O13D N1D O12D 116.4(3) . . ?
O11D N1D Ho1 176.6(2) . . ?
O13D N1D Ho1 60.60(17) . . ?
O12D N1D Ho1 55.79(16) . . ?
N1D O12D Ho1 98.3(2) . . ?
N1D O13D Ho1 93.65(19) . . ?
C1E O1E Ho1 129.0(3) . . ?
C1E O1E H1E 102(4) . . ?
Ho1 O1E H1E 125(4) . . ?
O1E C1E H1E1 109.5 . . ?
O1E C1E H1E2 109.5 . . ?
H1E1 C1E H1E2 109.5 . . ?
O1E C1E H1E3 109.5 . . ?
H1E1 C1E H1E3 109.5 . . ?
H1E2 C1E H1E3 109.5 . . ?
N1F C2F C3F 179.3(7) . . ?
C2F C3F H3F1 109.5 . . ?
C2F C3F H3F2 109.5 . . ?
H3F1 C3F H3F2 109.5 . . ?
C2F C3F H3F3 109.5 . . ?
H3F1 C3F H3F3 109.5 . . ?
H3F2 C3F H3F3 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6A N1A C2A C3A -0.9(5) . . . . ?
Ho1 N1A C2A C3A -173.7(3) . . . . ?
N1A C2A C3A C4A -1.9(6) . . . . ?
C2A C3A C4A C5A 2.0(6) . . . . ?
C3A C4A C5A C6A 0.6(6) . . . . ?
C2A N1A C6A N7A -177.3(3) . . . . ?
Ho1 N1A C6A N7A -4.5(4) . . . . ?
C2A N1A C6A C5A 3.6(5) . . . . ?
Ho1 N1A C6A C5A 176.4(3) . . . . ?
C4A C5A C6A N1A -3.5(5) . . . . ?
C4A C5A C6A N7A 177.5(3) . . . . ?
N1A C6A N7A N8A -7.1(5) . . . . ?
C5A C6A N7A N8A 172.0(3) . . . . ?
N1A C6A N7A C71A 174.2(3) . . . . ?
C5A C6A N7A C71A -6.7(5) . . . . ?
C6A N7A N8A C9A -170.1(3) . . . . ?
C71A N7A N8A C9A 8.6(5) . . . . ?
C6A N7A N8A Ho1 15.7(4) . . . . ?
C71A N7A N8A Ho1 -165.6(2) . . . . ?
N7A N8A C9A C10A 179.5(3) . . . . ?
Ho1 N8A C9A C10A -6.3(4) . . . . ?
N8A C9A C10A N14A -4.5(5) . . . . ?
N8A C9A C10A N11A 173.9(3) . . . . ?
N14A C10A N11A C12A 0.1(4) . . . . ?
C9A C10A N11A C12A -178.5(3) . . . . ?
N14A C10A N11A C11A 178.4(3) . . . . ?
C9A C10A N11A C11A -0.2(6) . . . . ?
C10A N11A C12A C13A -0.2(4) . . . . ?
C11A N11A C12A C13A -178.5(3) . . . . ?
N11A C12A C13A N14A 0.3(4) . . . . ?
N11A C10A N14A C13A 0.1(4) . . . . ?
C9A C10A N14A C13A 178.7(3) . . . . ?
N11A C10A N14A Ho1 -166.1(2) . . . . ?
C9A C10A N14A Ho1 12.5(4) . . . . ?
C12A C13A N14A C10A -0.3(4) . . . . ?
C12A C13A N14A Ho1 160.7(3) . . . . ?
O11B N1B O12B Ho1 -172.9(3) . . . . ?
O13B N1B O12B Ho1 6.6(3) . . . . ?
O11B N1B O13B Ho1 172.6(3) . . . . ?
O12B N1B O13B Ho1 -6.9(3) . . . . ?
O11C N1C O12C Ho1 -179.2(3) . . . . ?
O13C N1C O12C Ho1 0.8(3) . . . . ?
O11C N1C O13C Ho1 179.2(3) . . . . ?
O12C N1C O13C Ho1 -0.8(3) . . . . ?
O11D N1D O12D Ho1 178.3(3) . . . . ?
O13D N1D O12D Ho1 -1.8(3) . . . . ?
O11D N1D O13D Ho1 -178.4(3) . . . . ?
O12D N1D O13D Ho1 1.7(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C2A H2A O11B 0.95 2.55 3.435(5) 154.6 2_665
C5A H5A O12D 0.95 2.47 3.363(4) 156.1 2_666
C71A H71C O11C 0.98 2.41 3.249(5) 143.8 2_656
C11A H11B O13C 0.98 2.55 3.465(4) 155.8 2_556
O1E H1E O13B 0.80(5) 1.97(6) 2.767(4) 175(5) 2_665
C1E H1E1 O12C 0.98 2.45 3.025(5) 117.1 .
C1E H1E2 O11B 0.98 2.53 3.428(5) 152.9 1_655
C1E H1E3 O11D 0.98 2.54 3.509(5) 172.1 2_665


_refine_diff_density_max         1.470
_refine_diff_density_min         -1.498
_refine_diff_density_rms         0.142

_shelxl_version_number           2013-4


loop_
_publcif_info_exptl_table_extra_item
sin_theta_over_lambda_max

loop_
_publcif_info_exptl_table_header_item
?
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_09
_database_code_depnum_ccdc_archive 'CCDC 1435578'
_audit_update_record             
;
2015-11-06 deposited with the CCDC.	2024-07-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H29 F6 Ho N11 O6 S2, C F3 O3 S'
_chemical_formula_sum            'C27 H29 F9 Ho N11 O9 S3'
_chemical_formula_weight         1083.72

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ho Ho -0.2175 4.6783 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   18.7750(7)
_cell_length_b                   10.2574(2)
_cell_length_c                   21.0038(6)
_cell_angle_alpha                90
_cell_angle_beta                 101.760(3)
_cell_angle_gamma                90
_cell_volume                     3960.1(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(1)
_cell_measurement_reflns_used    5992
_cell_measurement_theta_min      3.5630
_cell_measurement_theta_max      28.0050

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.818
_exptl_crystal_F_000             2144
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_exptl_absorpt_coefficient_mu    2.262
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.82116
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.34a (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?

_diffrn_ambient_temperature      120(1)
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Eos
_diffrn_detector_area_resol_mean 16.1544
_diffrn_measurement_method       ω-scan
_diffrn_reflns_number            14768
_diffrn_reflns_av_unetI/netI     0.0258
_diffrn_reflns_av_R_equivalents  0.0167
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.976
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             6967
_reflns_number_gt                6291
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlis Pro (Agilent Technologies (2011))'
_computing_cell_refinement       'CrysAlis Pro (Agilent Technologies (2011))'
_computing_data_reduction        'CrysAlis Pro (Agilent Technologies (2011))'
_computing_structure_solution    'SIR92 (Altomare et al., 1993)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'Mercury (MacRae et al., 2009)'
_computing_publication_material  'SHELXL-2014 (Sheldrick, 2014)'

_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0424P)²+3.4842P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6967
_refine_ls_number_parameters     546
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0592
_refine_ls_R_factor_gt           0.0531
_refine_ls_wR_factor_ref         0.1409
_refine_ls_wR_factor_gt          0.1389
_refine_ls_goodness_of_fit_ref   1.967
_refine_ls_restrained_S_all      1.967
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Ho1 Ho 0.77340(2) 0.51318(3) 0.58976(2) 0.02259(12) Uani 1 1 d . . . . .
N1A N 0.8417(3) 0.6941(5) 0.5447(2) 0.0243(11) Uani 1 1 d . . . . .
C2A C 0.9011(4) 0.7490(7) 0.5818(3) 0.0357(17) Uani 1 1 d . . . . .
H2A H 0.9152 0.7215 0.6258 0.043 Uiso 1 1 calc R U . . .
C3A C 0.9421(5) 0.8416(10) 0.5599(4) 0.067(3) Uani 1 1 d . . . . .
H3A H 0.9849 0.8745 0.5874 0.080 Uiso 1 1 calc R U . . .
C4A C 0.9204(7) 0.8870(13) 0.4967(5) 0.107(5) Uani 1 1 d . . . . .
H4A H 0.9468 0.9543 0.4807 0.128 Uiso 1 1 calc R U . . .
C5A C 0.8596(5) 0.8324(9) 0.4574(4) 0.060(3) Uani 1 1 d . . . . .
H5A H 0.8441 0.8603 0.4136 0.072 Uiso 1 1 calc R U . . .
C6A C 0.8218(3) 0.7372(6) 0.4827(3) 0.0242(13) Uani 1 1 d . . . . .
N7A N 0.7596(3) 0.6853(5) 0.4458(2) 0.0275(12) Uani 1 1 d . . . . .
C71A C 0.7387(4) 0.7024(8) 0.3758(3) 0.0411(19) Uani 1 1 d . . . . .
H71A H 0.6930 0.7514 0.3653 0.062 Uiso 1 1 calc R U . . .
H71B H 0.7322 0.6169 0.3547 0.062 Uiso 1 1 calc R U . . .
H71C H 0.7769 0.7506 0.3602 0.062 Uiso 1 1 calc R U . . .
N8A N 0.7208(3) 0.6032(5) 0.4767(2) 0.0228(11) Uani 1 1 d . . . . .
C9A C 0.6605(3) 0.5562(6) 0.4457(3) 0.0244(13) Uani 1 1 d . . . . .
H9A H 0.6410 0.5787 0.4017 0.029 Uiso 1 1 calc R U . . .
C10A C 0.6239(4) 0.4676(6) 0.4811(3) 0.0271(14) Uani 1 1 d . . . . .
N11A N 0.5613(3) 0.4034(5) 0.4574(3) 0.0305(13) Uani 1 1 d . . . . .
C11A C 0.5185(4) 0.4101(7) 0.3907(4) 0.0421(18) Uani 1 1 d . . . . .
H11A H 0.5133 0.5013 0.3767 0.063 Uiso 1 1 calc R U . . .
H11B H 0.4703 0.3722 0.3893 0.063 Uiso 1 1 calc R U . . .
H11C H 0.5434 0.3611 0.3616 0.063 Uiso 1 1 calc R U . . .
C12A C 0.5473(4) 0.3267(7) 0.5065(4) 0.0386(17) Uani 1 1 d . . . . .
H12A H 0.5065 0.2712 0.5048 0.046 Uiso 1 1 calc R U . . .
C13A C 0.6022(4) 0.3445(7) 0.5577(4) 0.0355(16) Uani 1 1 d . . . . .
H13A H 0.6067 0.3022 0.5985 0.043 Uiso 1 1 calc R U . . .
N14A N 0.6510(3) 0.4326(5) 0.5425(2) 0.0282(12) Uani 1 1 d . . . . .
N1B N 0.7796(3) 0.3008(5) 0.6511(3) 0.0296(13) Uani 1 1 d . . . . .
C2B C 0.8217(4) 0.2025(7) 0.6366(3) 0.0350(16) Uani 1 1 d . . . . .
H2B H 0.8446 0.2137 0.6006 0.042 Uiso 1 1 calc R U . . .
C3B C 0.8333(4) 0.0877(7) 0.6707(3) 0.0351(16) Uani 1 1 d . . . . .
H3B H 0.8624 0.0203 0.6582 0.042 Uiso 1 1 calc R U . . .
C4B C 0.8009(4) 0.0738(7) 0.7241(4) 0.0396(18) Uani 1 1 d . . . . .
H4B H 0.8086 -0.0034 0.7495 0.048 Uiso 1 1 calc R U . . .
C5B C 0.7580(4) 0.1702(7) 0.7401(4) 0.0360(17) Uani 1 1 d . . . . .
H5B H 0.7368 0.1620 0.7773 0.043 Uiso 1 1 calc R U . . .
C6B C 0.7456(4) 0.2830(6) 0.7007(3) 0.0273(14) Uani 1 1 d . . . . .
N7B N 0.6998(3) 0.3805(5) 0.7129(3) 0.0317(13) Uani 1 1 d . . . . .
C71B C 0.6539(5) 0.3726(7) 0.7611(4) 0.046(2) Uani 1 1 d . . . . .
H71D H 0.6739 0.4285 0.7982 0.070 Uiso 1 1 calc R U . . .
H71E H 0.6523 0.2822 0.7759 0.070 Uiso 1 1 calc R U . . .
H71F H 0.6045 0.4016 0.7415 0.070 Uiso 1 1 calc R U . . .
N8B N 0.7009(3) 0.4933(5) 0.6799(3) 0.0279(13) Uani 1 1 d . . . . .
C9B C 0.6671(3) 0.5940(6) 0.6942(3) 0.0278(14) Uani 1 1 d . . . . .
H9B H 0.6408 0.5933 0.7283 0.033 Uiso 1 1 calc R U . . .
C10B C 0.6715(3) 0.7071(6) 0.6559(3) 0.0256(14) Uani 1 1 d . . . . .
N11B N 0.6437(3) 0.8273(5) 0.6655(3) 0.0253(12) Uani 1 1 d . . . . .
C11B C 0.6085(4) 0.8630(7) 0.7192(3) 0.0367(17) Uani 1 1 d . . . . .
H11D H 0.5615 0.8184 0.7139 0.055 Uiso 1 1 calc R U . . .
H11E H 0.6009 0.9575 0.7190 0.055 Uiso 1 1 calc R U . . .
H11F H 0.6396 0.8369 0.7605 0.055 Uiso 1 1 calc R U . . .
C12B C 0.6583(4) 0.9068(6) 0.6170(3) 0.0305(15) Uani 1 1 d . . . . .
H12B H 0.6455 0.9961 0.6103 0.037 Uiso 1 1 calc R U . . .
C13B C 0.6943(4) 0.8328(6) 0.5808(3) 0.0296(15) Uani 1 1 d . . . . .
H13B H 0.7110 0.8631 0.5436 0.035 Uiso 1 1 calc R U . . .
N14B N 0.7038(3) 0.7086(5) 0.6045(2) 0.0258(12) Uani 1 1 d . . . . .
S1C S 0.86027(9) 0.64002(16) 0.75388(8) 0.0299(4) Uani 1 1 d . . . . .
O11C O 0.8417(2) 0.5986(5) 0.6867(2) 0.0315(11) Uani 1 1 d . . . . .
O12C O 0.8671(4) 0.7755(5) 0.7617(3) 0.078(2) Uani 1 1 d . . . . .
O13C O 0.8212(3) 0.5735(7) 0.7959(2) 0.0577(16) Uani 1 1 d . . . . .
C1C C 0.9532(5) 0.5816(12) 0.7790(4) 0.063(3) Uani 1 1 d . . . . .
F11C F 0.9949(3) 0.6334(9) 0.7421(3) 0.106(3) Uani 1 1 d . . . . .
F12C F 0.9561(4) 0.4541(7) 0.7744(3) 0.108(3) Uani 1 1 d . . . . .
F13C F 0.9796(3) 0.6150(7) 0.8408(2) 0.0772(18) Uani 1 1 d . . . . .
S1D S 0.81291(18) 0.3181(2) 0.45351(12) 0.0709(8) Uani 1 1 d . . . . .
O11D O 0.7896(3) 0.3645(5) 0.5102(2) 0.0377(12) Uani 1 1 d . . . . .
O12D O 0.8899(4) 0.2321(12) 0.4767(4) 0.127(4) Uani 1 1 d . . . . .
O13D O 0.8138(5) 0.3998(7) 0.4044(4) 0.096(3) Uani 1 1 d . . . . .
C1D C 0.7594(8) 0.1832(13) 0.4342(6) 0.090(4) Uani 1 1 d . U . . .
F11D F 0.6935(5) 0.2450(10) 0.4099(4) 0.165(5) Uani 1 1 d . . . . .
F12D F 0.7845(7) 0.1141(7) 0.3878(4) 0.183(5) Uani 1 1 d . . . . .
F13D F 0.7612(5) 0.0986(6) 0.4806(4) 0.119(3) Uani 1 1 d . . . . .
N1E N 0.9068(3) 0.4507(6) 0.6041(3) 0.0362(14) Uani 1 1 d . . . . .
C2E C 0.9660(5) 0.4387(8) 0.6045(4) 0.0462(19) Uani 1 1 d . . . . .
C3E C 1.0431(5) 0.4301(15) 0.6054(7) 0.109(5) Uani 1 1 d . . . . .
H3E1 H 1.0508 0.3818 0.5671 0.164 Uiso 1 1 calc R U . . .
H3E2 H 1.0675 0.3847 0.6449 0.164 Uiso 1 1 calc R U . . .
H3E3 H 1.0634 0.5181 0.6049 0.164 Uiso 1 1 calc R U . . .
S1F S 0.51404(9) -0.15533(15) 0.33315(8) 0.0292(4) Uani 1 1 d . . . . .
O11F O 0.5474(3) -0.2794(5) 0.3525(3) 0.0444(13) Uani 1 1 d . . . . .
O12F O 0.4391(3) -0.1459(4) 0.3376(3) 0.0384(12) Uani 1 1 d . . . . .
O13F O 0.5324(3) -0.0999(5) 0.2756(2) 0.0414(12) Uani 1 1 d . . . . .
C1F C 0.5597(4) -0.0462(8) 0.3970(4) 0.0409(18) Uani 1 1 d . . . . .
F11F F 0.5470(3) -0.0788(6) 0.4548(2) 0.0746(17) Uani 1 1 d . . . . .
F12F F 0.5390(3) 0.0766(4) 0.3857(3) 0.0618(14) Uani 1 1 d . . . . .
F13F F 0.6313(3) -0.0493(5) 0.4025(3) 0.0588(13) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ho1 O11D 2.328(5) . ?
Ho1 O11C 2.343(4) . ?
Ho1 N14B 2.447(5) . ?
Ho1 N14A 2.453(5) . ?
Ho1 N1B 2.521(5) . ?
Ho1 N1E 2.543(6) . ?
Ho1 N1A 2.546(5) . ?
Ho1 N8A 2.551(5) . ?
Ho1 N8B 2.555(6) . ?
N1A C2A 1.347(8) . ?
N1A C6A 1.353(8) . ?
C2A C3A 1.361(10) . ?
C2A H2A 0.9500 . ?
C3A C4A 1.388(13) . ?
C3A H3A 0.9500 . ?
C4A C5A 1.384(12) . ?
C4A H4A 0.9500 . ?
C5A C6A 1.375(9) . ?
C5A H5A 0.9500 . ?
C6A N7A 1.371(8) . ?
N7A N8A 1.363(7) . ?
N7A C71A 1.452(8) . ?
C71A H71A 0.9800 . ?
C71A H71B 0.9800 . ?
C71A H71C 0.9800 . ?
N8A C9A 1.280(8) . ?
C9A C10A 1.435(9) . ?
C9A H9A 0.9500 . ?
C10A N14A 1.335(8) . ?
C10A N11A 1.351(8) . ?
N11A C12A 1.366(9) . ?
N11A C11A 1.467(9) . ?
C11A H11A 0.9800 . ?
C11A H11B 0.9800 . ?
C11A H11C 0.9800 . ?
C12A C13A 1.341(10) . ?
C12A H12A 0.9500 . ?
C13A N14A 1.370(8) . ?
C13A H13A 0.9500 . ?
N1B C6B 1.341(8) . ?
N1B C2B 1.353(8) . ?
C2B C3B 1.373(10) . ?
C2B H2B 0.9500 . ?
C3B C4B 1.388(10) . ?
C3B H3B 0.9500 . ?
C4B C5B 1.360(10) . ?
C4B H4B 0.9500 . ?
C5B C6B 1.414(9) . ?
C5B H5B 0.9500 . ?
C6B N7B 1.377(9) . ?
N7B N8B 1.351(7) . ?
N7B C71B 1.460(9) . ?
C71B H71D 0.9800 . ?
C71B H71E 0.9800 . ?
C71B H71F 0.9800 . ?
N8B C9B 1.280(8) . ?
C9B C10B 1.423(9) . ?
C9B H9B 0.9500 . ?
C10B N14B 1.341(8) . ?
C10B N11B 1.370(8) . ?
N11B C12B 1.376(8) . ?
N11B C11B 1.463(8) . ?
C11B H11D 0.9800 . ?
C11B H11E 0.9800 . ?
C11B H11F 0.9800 . ?
C12B C13B 1.349(9) . ?
C12B H12B 0.9500 . ?
C13B N14B 1.367(8) . ?
C13B H13B 0.9500 . ?
S1C O12C 1.402(6) . ?
S1C O13C 1.431(6) . ?
S1C O11C 1.448(5) . ?
S1C C1C 1.819(9) . ?
C1C F12C 1.314(14) . ?
C1C F11C 1.320(11) . ?
C1C F13C 1.337(9) . ?
S1D O13D 1.333(7) . ?
S1D O11D 1.430(5) . ?
S1D C1D 1.710(14) . ?
S1D O12D 1.679(9) . ?
C1D F13D 1.300(14) . ?
C1D F12D 1.364(14) . ?
C1D F11D 1.390(15) . ?
N1E C2E 1.118(9) . ?
C2E C3E 1.447(12) . ?
C3E H3E1 0.9800 . ?
C3E H3E2 0.9800 . ?
C3E H3E3 0.9800 . ?
S1F O12F 1.433(5) . ?
S1F O11F 1.440(5) . ?
S1F O13F 1.440(5) . ?
S1F C1F 1.822(8) . ?
C1F F12F 1.326(9) . ?
C1F F13F 1.324(9) . ?
C1F F11F 1.328(8) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O11D Ho1 O11C 137.74(17) . . ?
O11D Ho1 N14B 141.18(16) . . ?
O11C Ho1 N14B 78.19(17) . . ?
O11D Ho1 N14A 74.79(18) . . ?
O11C Ho1 N14A 141.16(17) . . ?
N14B Ho1 N14A 81.17(18) . . ?
O11D Ho1 N1B 78.56(17) . . ?
O11C Ho1 N1B 85.35(17) . . ?
N14B Ho1 N1B 127.80(17) . . ?
N14A Ho1 N1B 81.83(18) . . ?
O11D Ho1 N1E 69.54(19) . . ?
O11C Ho1 N1E 68.89(18) . . ?
N14B Ho1 N1E 136.90(19) . . ?
N14A Ho1 N1E 141.4(2) . . ?
N1B Ho1 N1E 77.26(19) . . ?
O11D Ho1 N1A 93.50(17) . . ?
O11C Ho1 N1A 79.79(16) . . ?
N14B Ho1 N1A 76.87(17) . . ?
N14A Ho1 N1A 126.60(17) . . ?
N1B Ho1 N1A 147.73(17) . . ?
N1E Ho1 N1A 70.70(18) . . ?
O11D Ho1 N8A 69.60(16) . . ?
O11C Ho1 N8A 135.45(17) . . ?
N14B Ho1 N8A 72.92(16) . . ?
N14A Ho1 N8A 65.94(17) . . ?
N1B Ho1 N8A 139.20(17) . . ?
N1E Ho1 N8A 112.76(18) . . ?
N1A Ho1 N8A 61.23(16) . . ?
O11D Ho1 N8B 130.31(17) . . ?
O11C Ho1 N8B 70.48(16) . . ?
N14B Ho1 N8B 65.95(17) . . ?
N14A Ho1 N8B 71.13(17) . . ?
N1B Ho1 N8B 61.86(17) . . ?
N1E Ho1 N8B 123.51(19) . . ?
N1A Ho1 N8B 135.95(16) . . ?
N8A Ho1 N8B 123.71(17) . . ?
C2A N1A C6A 117.0(5) . . ?
C2A N1A Ho1 120.6(4) . . ?
C6A N1A Ho1 122.3(4) . . ?
N1A C2A C3A 123.7(7) . . ?
N1A C2A H2A 118.2 . . ?
C3A C2A H2A 118.2 . . ?
C2A C3A C4A 118.8(8) . . ?
C2A C3A H3A 120.6 . . ?
C4A C3A H3A 120.6 . . ?
C5A C4A C3A 118.7(8) . . ?
C5A C4A H4A 120.6 . . ?
C3A C4A H4A 120.6 . . ?
C6A C5A C4A 119.0(7) . . ?
C6A C5A H5A 120.5 . . ?
C4A C5A H5A 120.5 . . ?
N1A C6A C5A 122.7(6) . . ?
N1A C6A N7A 117.0(5) . . ?
C5A C6A N7A 120.2(6) . . ?
N8A N7A C6A 116.5(5) . . ?
N8A N7A C71A 119.8(5) . . ?
C6A N7A C71A 123.3(5) . . ?
N7A C71A H71A 109.5 . . ?
N7A C71A H71B 109.5 . . ?
H71A C71A H71B 109.5 . . ?
N7A C71A H71C 109.5 . . ?
H71A C71A H71C 109.5 . . ?
H71B C71A H71C 109.5 . . ?
C9A N8A N7A 119.6(5) . . ?
C9A N8A Ho1 118.1(4) . . ?
N7A N8A Ho1 121.6(4) . . ?
N8A C9A C10A 116.2(6) . . ?
N8A C9A H9A 121.9 . . ?
C10A C9A H9A 121.9 . . ?
N14A C10A N11A 111.0(6) . . ?
N14A C10A C9A 122.8(6) . . ?
N11A C10A C9A 126.1(6) . . ?
C10A N11A C12A 106.7(6) . . ?
C10A N11A C11A 126.6(6) . . ?
C12A N11A C11A 126.6(6) . . ?
N11A C11A H11A 109.5 . . ?
N11A C11A H11B 109.5 . . ?
H11A C11A H11B 109.5 . . ?
N11A C11A H11C 109.5 . . ?
H11A C11A H11C 109.5 . . ?
H11B C11A H11C 109.5 . . ?
C13A C12A N11A 107.0(6) . . ?
C13A C12A H12A 126.5 . . ?
N11A C12A H12A 126.5 . . ?
C12A C13A N14A 110.2(6) . . ?
C12A C13A H13A 124.9 . . ?
N14A C13A H13A 124.9 . . ?
C10A N14A C13A 105.1(6) . . ?
C10A N14A Ho1 116.2(4) . . ?
C13A N14A Ho1 138.0(5) . . ?
C6B N1B C2B 117.8(6) . . ?
C6B N1B Ho1 122.4(4) . . ?
C2B N1B Ho1 119.8(5) . . ?
N1B C2B C3B 124.0(7) . . ?
N1B C2B H2B 118.0 . . ?
C3B C2B H2B 118.0 . . ?
C2B C3B C4B 117.4(7) . . ?
C2B C3B H3B 121.3 . . ?
C4B C3B H3B 121.3 . . ?
C5B C4B C3B 120.3(7) . . ?
C5B C4B H4B 119.8 . . ?
C3B C4B H4B 119.8 . . ?
C4B C5B C6B 119.0(7) . . ?
C4B C5B H5B 120.5 . . ?
C6B C5B H5B 120.5 . . ?
N1B C6B N7B 117.4(6) . . ?
N1B C6B C5B 121.2(6) . . ?
N7B C6B C5B 121.4(6) . . ?
N8B N7B C6B 116.8(5) . . ?
N8B N7B C71B 118.5(5) . . ?
C6B N7B C71B 124.6(6) . . ?
N7B C71B H71D 109.5 . . ?
N7B C71B H71E 109.5 . . ?
H71D C71B H71E 109.5 . . ?
N7B C71B H71F 109.5 . . ?
H71D C71B H71F 109.5 . . ?
H71E C71B H71F 109.5 . . ?
C9B N8B N7B 120.7(6) . . ?
C9B N8B Ho1 118.3(4) . . ?
N7B N8B Ho1 121.0(4) . . ?
N8B C9B C10B 116.0(6) . . ?
N8B C9B H9B 122.0 . . ?
C10B C9B H9B 122.0 . . ?
N14B C10B N11B 110.9(6) . . ?
N14B C10B C9B 123.4(6) . . ?
N11B C10B C9B 125.7(6) . . ?
C10B N11B C12B 106.5(5) . . ?
C10B N11B C11B 125.7(5) . . ?
C12B N11B C11B 127.7(5) . . ?
N11B C11B H11D 109.5 . . ?
N11B C11B H11E 109.5 . . ?
H11D C11B H11E 109.5 . . ?
N11B C11B H11F 109.5 . . ?
H11D C11B H11F 109.5 . . ?
H11E C11B H11F 109.5 . . ?
C13B C12B N11B 106.5(6) . . ?
C13B C12B H12B 126.8 . . ?
N11B C12B H12B 126.8 . . ?
C12B C13B N14B 111.2(6) . . ?
C12B C13B H13B 124.4 . . ?
N14B C13B H13B 124.4 . . ?
C10B N14B C13B 104.9(5) . . ?
C10B N14B Ho1 115.7(4) . . ?
C13B N14B Ho1 138.6(4) . . ?
O12C S1C O13C 116.5(5) . . ?
O12C S1C O11C 113.8(4) . . ?
O13C S1C O11C 114.2(3) . . ?
O12C S1C C1C 103.5(5) . . ?
O13C S1C C1C 104.3(4) . . ?
O11C S1C C1C 102.3(3) . . ?
S1C O11C Ho1 159.7(3) . . ?
F12C C1C F11C 108.7(8) . . ?
F12C C1C F13C 108.2(8) . . ?
F11C C1C F13C 108.7(9) . . ?
F12C C1C S1C 111.0(7) . . ?
F11C C1C S1C 110.3(7) . . ?
F13C C1C S1C 109.9(6) . . ?
O13D S1D O11D 119.3(4) . . ?
O13D S1D C1D 115.1(6) . . ?
O11D S1D C1D 101.6(5) . . ?
O13D S1D O12D 114.2(6) . . ?
O11D S1D O12D 109.0(4) . . ?
C1D S1D O12D 94.2(6) . . ?
S1D O11D Ho1 157.2(3) . . ?
F13D C1D F12D 103.2(11) . . ?
F13D C1D F11D 117.7(12) . . ?
F12D C1D F11D 112.7(10) . . ?
F13D C1D S1D 116.0(9) . . ?
F12D C1D S1D 108.6(10) . . ?
F11D C1D S1D 98.9(9) . . ?
C2E N1E Ho1 169.5(6) . . ?
N1E C2E C3E 177.1(11) . . ?
C2E C3E H3E1 109.5 . . ?
C2E C3E H3E2 109.5 . . ?
H3E1 C3E H3E2 109.5 . . ?
C2E C3E H3E3 109.5 . . ?
H3E1 C3E H3E3 109.5 . . ?
H3E2 C3E H3E3 109.5 . . ?
O12F S1F O11F 114.7(3) . . ?
O12F S1F O13F 115.8(3) . . ?
O11F S1F O13F 114.9(3) . . ?
O12F S1F C1F 103.4(3) . . ?
O11F S1F C1F 102.9(4) . . ?
O13F S1F C1F 102.6(3) . . ?
F12F C1F F13F 107.1(6) . . ?
F12F C1F F11F 107.6(7) . . ?
F13F C1F F11F 106.5(7) . . ?
F12F C1F S1F 112.0(5) . . ?
F13F C1F S1F 111.5(5) . . ?
F11F C1F S1F 111.9(5) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6A N1A C2A C3A -1.6(11) . . . . ?
Ho1 N1A C2A C3A 176.8(7) . . . . ?
N1A C2A C3A C4A 2.9(16) . . . . ?
C2A C3A C4A C5A -3(2) . . . . ?
C3A C4A C5A C6A 1(2) . . . . ?
C2A N1A C6A C5A 0.1(10) . . . . ?
Ho1 N1A C6A C5A -178.2(6) . . . . ?
C2A N1A C6A N7A -177.4(6) . . . . ?
Ho1 N1A C6A N7A 4.3(8) . . . . ?
C4A C5A C6A N1A -0.1(15) . . . . ?
C4A C5A C6A N7A 177.3(10) . . . . ?
N1A C6A N7A N8A 5.2(8) . . . . ?
C5A C6A N7A N8A -172.4(7) . . . . ?
N1A C6A N7A C71A -167.9(6) . . . . ?
C5A C6A N7A C71A 14.5(11) . . . . ?
C6A N7A N8A C9A 176.8(6) . . . . ?
C71A N7A N8A C9A -9.9(9) . . . . ?
C6A N7A N8A Ho1 -12.4(7) . . . . ?
C71A N7A N8A Ho1 160.9(5) . . . . ?
N7A N8A C9A C10A 178.3(5) . . . . ?
Ho1 N8A C9A C10A 7.1(7) . . . . ?
N8A C9A C10A N14A -1.4(9) . . . . ?
N8A C9A C10A N11A -177.5(6) . . . . ?
N14A C10A N11A C12A 1.5(8) . . . . ?
C9A C10A N11A C12A 178.0(6) . . . . ?
N14A C10A N11A C11A -175.8(6) . . . . ?
C9A C10A N11A C11A 0.6(11) . . . . ?
C10A N11A C12A C13A -1.3(8) . . . . ?
C11A N11A C12A C13A 176.0(7) . . . . ?
N11A C12A C13A N14A 0.7(8) . . . . ?
N11A C10A N14A C13A -1.1(7) . . . . ?
C9A C10A N14A C13A -177.7(6) . . . . ?
N11A C10A N14A Ho1 171.4(4) . . . . ?
C9A C10A N14A Ho1 -5.2(8) . . . . ?
C12A C13A N14A C10A 0.2(8) . . . . ?
C12A C13A N14A Ho1 -169.6(5) . . . . ?
C6B N1B C2B C3B -2.0(10) . . . . ?
Ho1 N1B C2B C3B 174.4(5) . . . . ?
N1B C2B C3B C4B -1.5(11) . . . . ?
C2B C3B C4B C5B 1.6(11) . . . . ?
C3B C4B C5B C6B 1.6(11) . . . . ?
C2B N1B C6B N7B -176.6(6) . . . . ?
Ho1 N1B C6B N7B 7.0(8) . . . . ?
C2B N1B C6B C5B 5.4(9) . . . . ?
Ho1 N1B C6B C5B -171.0(5) . . . . ?
C4B C5B C6B N1B -5.3(10) . . . . ?
C4B C5B C6B N7B 176.8(6) . . . . ?
N1B C6B N7B N8B -9.0(9) . . . . ?
C5B C6B N7B N8B 169.0(6) . . . . ?
N1B C6B N7B C71B 174.5(7) . . . . ?
C5B C6B N7B C71B -7.5(10) . . . . ?
C6B N7B N8B C9B -171.2(6) . . . . ?
C71B N7B N8B C9B 5.6(9) . . . . ?
C6B N7B N8B Ho1 7.0(8) . . . . ?
C71B N7B N8B Ho1 -176.2(5) . . . . ?
N7B N8B C9B C10B -179.5(6) . . . . ?
Ho1 N8B C9B C10B 2.3(8) . . . . ?
N8B C9B C10B N14B 5.0(9) . . . . ?
N8B C9B C10B N11B -175.4(6) . . . . ?
N14B C10B N11B C12B 1.1(7) . . . . ?
C9B C10B N11B C12B -178.5(6) . . . . ?
N14B C10B N11B C11B -176.4(6) . . . . ?
C9B C10B N11B C11B 4.0(10) . . . . ?
C10B N11B C12B C13B -0.5(7) . . . . ?
C11B N11B C12B C13B 177.0(6) . . . . ?
N11B C12B C13B N14B -0.3(8) . . . . ?
N11B C10B N14B C13B -1.3(7) . . . . ?
C9B C10B N14B C13B 178.4(6) . . . . ?
N11B C10B N14B Ho1 170.7(4) . . . . ?
C9B C10B N14B Ho1 -9.7(8) . . . . ?
C12B C13B N14B C10B 1.0(7) . . . . ?
C12B C13B N14B Ho1 -168.0(5) . . . . ?
O12C S1C O11C Ho1 -111.2(9) . . . . ?
O13C S1C O11C Ho1 26.0(10) . . . . ?
C1C S1C O11C Ho1 138.0(9) . . . . ?
O12C S1C C1C F12C 179.9(6) . . . . ?
O13C S1C C1C F12C 57.6(7) . . . . ?
O11C S1C C1C F12C -61.6(7) . . . . ?
O12C S1C C1C F11C -59.6(8) . . . . ?
O13C S1C C1C F11C 178.1(7) . . . . ?
O11C S1C C1C F11C 58.9(8) . . . . ?
O12C S1C C1C F13C 60.3(9) . . . . ?
O13C S1C C1C F13C -62.1(9) . . . . ?
O11C S1C C1C F13C 178.7(7) . . . . ?
O13D S1D O11D Ho1 -32.9(11) . . . . ?
C1D S1D O11D Ho1 -160.7(9) . . . . ?
O12D S1D O11D Ho1 100.6(9) . . . . ?
O13D S1D C1D F13D 176.1(9) . . . . ?
O11D S1D C1D F13D -53.4(11) . . . . ?
O12D S1D C1D F13D 56.9(11) . . . . ?
O13D S1D C1D F12D 60.6(11) . . . . ?
O11D S1D C1D F12D -169.0(8) . . . . ?
O12D S1D C1D F12D -58.6(9) . . . . ?
O13D S1D C1D F11D -57.0(9) . . . . ?
O11D S1D C1D F11D 73.4(8) . . . . ?
O12D S1D C1D F11D -176.2(7) . . . . ?
O12F S1F C1F F12F -63.9(6) . . . . ?
O11F S1F C1F F12F 176.4(5) . . . . ?
O13F S1F C1F F12F 56.8(6) . . . . ?
O12F S1F C1F F13F 176.1(5) . . . . ?
O11F S1F C1F F13F 56.4(6) . . . . ?
O13F S1F C1F F13F -63.2(6) . . . . ?
O12F S1F C1F F11F 56.9(7) . . . . ?
O11F S1F C1F F11F -62.8(7) . . . . ?
O13F S1F C1F F11F 177.7(6) . . . . ?

_refine_diff_density_max         2.867
_refine_diff_density_min         -2.257
_refine_diff_density_rms         0.141

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_22
_database_code_depnum_ccdc_archive 'CCDC 1052305'
_audit_update_record             
;
2016-01-10 deposited with the CCDC.	2024-07-03 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H17 N8 O10 Tm, C11 H14 N5, N O3'
_chemical_formula_sum            'C23 H31 N14 O13 Tm'
_chemical_formula_weight         880.55

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Tm Tm -8.0393 4.1821 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.3950(4)
_cell_length_b                   12.7332(6)
_cell_length_c                   16.9061(9)
_cell_angle_alpha                71.362(5)
_cell_angle_beta                 80.611(4)
_cell_angle_gamma                76.595(4)
_cell_volume                     1657.96(15)
_cell_formula_units_Z            2
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    8383
_cell_measurement_theta_min      3.7220
_cell_measurement_theta_max      75.0830

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.764
_exptl_crystal_F_000             880
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.07
_exptl_absorpt_coefficient_mu    5.762
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.28714
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     1.5418
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_source         'SuperNova (Cu) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'SuperNova, Single source at offset), Atlas'
_diffrn_detector_area_resol_mean 10.5357
_diffrn_measurement_method       ω-scan
_diffrn_reflns_number            11642
_diffrn_reflns_av_unetI/netI     0.0307
_diffrn_reflns_av_R_equivalents  0.0426
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.771
_diffrn_reflns_theta_max         75.902
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.962
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.962
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             6651
_reflns_number_gt                6370
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlis Pro (Agilent Technologies (2011))'
_computing_cell_refinement       'CrysAlis Pro (Agilent Technologies (2011))'
_computing_data_reduction        'CrysAlis Pro (Agilent Technologies (2011))'
_computing_structure_solution    'SIR92 (Altomare et al., 1993)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Mercury (MacRae et al., 2009)'
_computing_publication_material  'SHELXL-2013 (Sheldrick, 2013)'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0962P)²+5.3923P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6651
_refine_ls_number_parameters     465
_refine_ls_number_restraints     43
_refine_ls_R_factor_all          0.0607
_refine_ls_R_factor_gt           0.0593
_refine_ls_wR_factor_ref         0.1643
_refine_ls_wR_factor_gt          0.1630
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_restrained_S_all      1.121
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Tm1 Tm 0.69518(3) 0.19519(2) 0.64987(2) 0.03743(13) Uani 1 1 d . . . . .
N1A N 0.4995(6) 0.1370(4) 0.5838(4) 0.0432(11) Uani 1 1 d . . . . .
C2A C 0.4994(7) 0.1606(5) 0.5018(4) 0.0427(12) Uani 1 1 d . . . . .
C3A C 0.3787(8) 0.1339(6) 0.4666(5) 0.0535(16) Uani 1 1 d . . . . .
H3A H 0.3800 0.1500 0.4089 0.064 Uiso 1 1 calc R U . . .
C4A C 0.2576(8) 0.0827(6) 0.5212(6) 0.063(2) Uani 1 1 d . . . . .
H4A H 0.1760 0.0641 0.4999 0.075 Uiso 1 1 calc R U . . .
C5A C 0.2571(8) 0.0599(6) 0.6047(6) 0.0587(18) Uani 1 1 d . . . . .
H5A H 0.1750 0.0269 0.6413 0.070 Uiso 1 1 calc R U . . .
C6A C 0.3817(8) 0.0867(6) 0.6347(5) 0.0507(15) Uani 1 1 d . . . . .
H6A H 0.3836 0.0690 0.6924 0.061 Uiso 1 1 calc R U . . .
N7A N 0.6256(6) 0.2120(4) 0.4512(3) 0.0448(11) Uani 1 1 d . . . . .
C71A C 0.6500(10) 0.2357(7) 0.3606(5) 0.0599(17) Uani 1 1 d . . . . .
H71C H 0.6226 0.3157 0.3348 0.090 Uiso 1 1 calc R U . . .
H71B H 0.5805 0.1987 0.3432 0.090 Uiso 1 1 calc R U . . .
H71A H 0.7629 0.2084 0.3441 0.090 Uiso 1 1 calc R U . . .
N8A N 0.7298(6) 0.2394(4) 0.4908(3) 0.0376(9) Uani 1 1 d . . . . .
C9A C 0.8457(7) 0.2905(5) 0.4500(4) 0.0416(12) Uani 1 1 d . . . . .
H9A H 0.8622 0.3116 0.3918 0.050 Uiso 1 1 calc R U . . .
C10A C 0.9485(7) 0.3131(5) 0.5001(4) 0.0435(13) Uani 1 1 d . . . . .
N11A N 1.0796(6) 0.3643(4) 0.4710(4) 0.0506(13) Uani 1 1 d . . . . .
C11A C 1.1462(10) 0.4024(7) 0.3846(6) 0.068(2) Uani 1 1 d . . . . .
H11C H 1.1739 0.3401 0.3613 0.103 Uiso 1 1 calc R U . . .
H11B H 1.2431 0.4317 0.3820 0.103 Uiso 1 1 calc R U . . .
H11A H 1.0658 0.4606 0.3532 0.103 Uiso 1 1 calc R U . . .
C12A C 1.1417(8) 0.3682(6) 0.5395(5) 0.0571(17) Uani 1 1 d . . . . .
H12A H 1.2329 0.3980 0.5395 0.069 Uiso 1 1 calc R U . . .
C13A C 1.0433(9) 0.3194(6) 0.6086(5) 0.0529(15) Uani 1 1 d . . . . .
H13A H 1.0566 0.3107 0.6641 0.063 Uiso 1 1 calc R U . . .
N14A N 0.9220(6) 0.2854(4) 0.5823(3) 0.0436(11) Uani 1 1 d . . . . .
N1B N 0.5387(8) 0.4232(5) 0.6318(5) 0.0565(15) Uani 1 1 d . . . . .
O11B O 0.4753(10) 0.5218(5) 0.6180(6) 0.097(2) Uani 1 1 d . . . . .
O12B O 0.5055(6) 0.3603(4) 0.5951(4) 0.0587(12) Uani 1 1 d . . . . .
O13B O 0.6438(6) 0.3740(4) 0.6854(4) 0.0610(13) Uani 1 1 d . . . . .
N1C N 0.8204(7) -0.0389(5) 0.6688(4) 0.0517(13) Uani 1 1 d . . . . .
O11C O 0.8738(9) -0.1383(4) 0.6737(4) 0.0778(17) Uani 1 1 d . . . . .
O12C O 0.8752(5) 0.0385(4) 0.6104(3) 0.0497(10) Uani 1 1 d . . . . .
O13C O 0.7068(6) -0.0078(4) 0.7209(4) 0.0614(12) Uani 1 1 d . . . . .
O1D O 0.4862(7) 0.1834(5) 0.7604(4) 0.0655(14) Uani 1 1 d . . . . .
H1D H 0.4122 0.2393 0.7548 0.098 Uiso 1 1 d R U . . .
C1D C 0.463(2) 0.1083(13) 0.8386(9) 0.130(6) Uani 1 1 d . . . . .
H11D H 0.3617 0.0826 0.8434 0.196 Uiso 1 1 calc R U . . .
H12D H 0.4572 0.1451 0.8808 0.196 Uiso 1 1 calc R U . . .
H13D H 0.5527 0.0450 0.8463 0.196 Uiso 1 1 calc R U . . .
N1E N 0.9247(11) 0.0924(7) 0.8106(5) 0.118(3) Uani 1 1 d D U . . .
O11E O 0.8464(10) 0.1616(7) 0.7576(4) 0.104(2) Uani 1 1 d D U . . .
O12E O 0.900(2) 0.0771(12) 0.8867(5) 0.217(6) Uani 1 1 d D U . . .
O13E O 1.0496(18) 0.0255(13) 0.7855(10) 0.254(8) Uani 1 1 d D U . . .
N1F N 0.4549(10) 0.7113(7) -0.1599(5) 0.077(2) Uani 1 1 d . . . . .
C2F C 0.5426(9) 0.6540(7) -0.0961(5) 0.0606(17) Uani 1 1 d . . . . .
C3F C 0.5309(11) 0.6886(9) -0.0245(6) 0.076(2) Uani 1 1 d . . . . .
H3F H 0.5968 0.6478 0.0187 0.091 Uiso 1 1 calc R U . . .
C4F C 0.4199(14) 0.7842(10) -0.0198(8) 0.091(3) Uani 1 1 d . . . . .
H4F H 0.4071 0.8086 0.0276 0.109 Uiso 1 1 calc R U . . .
C5F C 0.3272(14) 0.8439(9) -0.0859(8) 0.093(3) Uani 1 1 d . . . . .
H5F H 0.2506 0.9090 -0.0840 0.111 Uiso 1 1 calc R U . . .
C6F C 0.3506(15) 0.8054(10) -0.1537(8) 0.093(3) Uani 1 1 d . . . . .
H6F H 0.2900 0.8472 -0.1988 0.112 Uiso 1 1 calc R U . . .
N7F N 0.6494(9) 0.5543(6) -0.1042(4) 0.0625(16) Uani 1 1 d . . . . .
C71F C 0.6596(14) 0.5119(10) -0.1766(6) 0.087(3) Uani 1 1 d . . . . .
H73F H 0.7689 0.5091 -0.2047 0.131 Uiso 1 1 calc R U . . .
H72F H 0.5823 0.5615 -0.2147 0.131 Uiso 1 1 calc R U . . .
H71F H 0.6344 0.4375 -0.1577 0.131 Uiso 1 1 calc R U . . .
N8F N 0.7425(8) 0.4964(6) -0.0399(4) 0.0613(15) Uani 1 1 d . . . . .
C9F C 0.8413(10) 0.4052(7) -0.0428(5) 0.0623(18) Uani 1 1 d . . . . .
H9F H 0.8541 0.3772 -0.0884 0.075 Uiso 1 1 calc R U . . .
C10F C 0.9329(9) 0.3477(6) 0.0298(5) 0.0595(17) Uani 1 1 d . . . . .
N11F N 1.0410(10) 0.2487(6) 0.0406(5) 0.0708(18) Uani 1 1 d . . . . .
C11F C 1.0924(16) 0.1841(9) -0.0200(7) 0.100(4) Uani 1 1 d . . . . .
H11F H 1.0007 0.1560 -0.0273 0.149 Uiso 1 1 calc R U . . .
H11G H 1.1796 0.1218 0.0004 0.149 Uiso 1 1 calc R U . . .
H11H H 1.1306 0.2320 -0.0728 0.149 Uiso 1 1 calc R U . . .
C12F C 1.0980(12) 0.2194(8) 0.1189(6) 0.076(2) Uani 1 1 d . . . . .
H12F H 1.1739 0.1553 0.1425 0.092 Uiso 1 1 calc R U . . .
C13F C 1.0227(11) 0.3011(7) 0.1539(6) 0.070(2) Uani 1 1 d . . . . .
H13F H 1.0355 0.3042 0.2067 0.085 Uiso 1 1 calc R U . . .
N14F N 0.9216(8) 0.3804(5) 0.0958(4) 0.0579(14) Uani 1 1 d . . . . .
H14F H 0.8609 0.4418 0.1028 0.069 Uiso 1 1 calc R U . . .
N1G N 0.7996(9) 0.5676(7) 0.2099(5) 0.0699(18) Uani 1 1 d . . . . .
O11G O 0.8830(12) 0.4770(8) 0.2425(6) 0.128(4) Uani 1 1 d . . . . .
O12G O 0.7498(10) 0.5821(7) 0.1425(5) 0.094(2) Uani 1 1 d . . . . .
O13G O 0.7697(9) 0.6433(8) 0.2447(6) 0.105(3) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Tm1 O11E 2.262(6) . ?
Tm1 O1D 2.338(5) . ?
Tm1 O12B 2.344(5) . ?
Tm1 N14A 2.391(5) . ?
Tm1 O12C 2.415(4) . ?
Tm1 O13B 2.463(5) . ?
Tm1 O13C 2.464(5) . ?
Tm1 N1A 2.487(5) . ?
Tm1 N8A 2.547(5) . ?
Tm1 N1B 2.837(5) . ?
Tm1 N1C 2.853(5) . ?
N1A C2A 1.322(9) . ?
N1A C6A 1.340(9) . ?
C2A N7A 1.397(8) . ?
C2A C3A 1.408(8) . ?
C3A C4A 1.388(12) . ?
C3A H3A 0.9300 . ?
C4A C5A 1.347(13) . ?
C4A H4A 0.9300 . ?
C5A C6A 1.385(9) . ?
C5A H5A 0.9300 . ?
C6A H6A 0.9300 . ?
N7A N8A 1.348(7) . ?
N7A C71A 1.451(9) . ?
C71A H71C 0.9600 . ?
C71A H71B 0.9600 . ?
C71A H71A 0.9600 . ?
N8A C9A 1.278(8) . ?
C9A C10A 1.433(9) . ?
C9A H9A 0.9300 . ?
C10A N14A 1.315(8) . ?
C10A N11A 1.352(8) . ?
N11A C12A 1.365(10) . ?
N11A C11A 1.444(10) . ?
C11A H11C 0.9600 . ?
C11A H11B 0.9600 . ?
C11A H11A 0.9600 . ?
C12A C13A 1.375(11) . ?
C12A H12A 0.9300 . ?
C13A N14A 1.378(8) . ?
C13A H13A 0.9300 . ?
N1B O11B 1.207(8) . ?
N1B O12B 1.259(8) . ?
N1B O13B 1.278(9) . ?
N1C O11C 1.221(8) . ?
N1C O12C 1.265(8) . ?
N1C O13C 1.271(8) . ?
O1D C1D 1.377(14) . ?
O1D H1D 0.8200 . ?
C1D H11D 0.9600 . ?
C1D H12D 0.9600 . ?
C1D H13D 0.9600 . ?
N1E O11E 1.196(7) . ?
N1E O12E 1.229(8) . ?
N1E O13E 1.294(8) . ?
N1F C2F 1.321(10) . ?
N1F C6F 1.333(14) . ?
C2F C3F 1.397(13) . ?
C2F N7F 1.407(11) . ?
C3F C4F 1.366(14) . ?
C3F H3F 0.9300 . ?
C4F C5F 1.378(16) . ?
C4F H4F 0.9300 . ?
C5F C6F 1.355(16) . ?
C5F H5F 0.9300 . ?
C6F H6F 0.9300 . ?
N7F N8F 1.353(9) . ?
N7F C71F 1.472(11) . ?
C71F H73F 0.9600 . ?
C71F H72F 0.9600 . ?
C71F H71F 0.9600 . ?
N8F C9F 1.272(11) . ?
C9F C10F 1.451(11) . ?
C9F H9F 0.9300 . ?
C10F N14F 1.292(10) . ?
C10F N11F 1.350(10) . ?
N11F C12F 1.389(12) . ?
N11F C11F 1.464(12) . ?
C11F H11F 0.9600 . ?
C11F H11G 0.9600 . ?
C11F H11H 0.9600 . ?
C12F C13F 1.341(14) . ?
C12F H12F 0.9300 . ?
C13F N14F 1.395(10) . ?
C13F H13F 0.9300 . ?
N14F H14F 0.8600 . ?
N1G O11G 1.212(10) . ?
N1G O12G 1.222(9) . ?
N1G O13G 1.242(10) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O11E Tm1 O1D 80.3(3) . . ?
O11E Tm1 O12B 126.4(3) . . ?
O1D Tm1 O12B 79.2(2) . . ?
O11E Tm1 N14A 77.7(2) . . ?
O1D Tm1 N14A 144.20(19) . . ?
O12B Tm1 N14A 91.57(19) . . ?
O11E Tm1 O12C 89.4(3) . . ?
O1D Tm1 O12C 126.37(18) . . ?
O12B Tm1 O12C 141.32(18) . . ?
N14A Tm1 O12C 81.38(16) . . ?
O11E Tm1 O13B 74.1(3) . . ?
O1D Tm1 O13B 73.33(19) . . ?
O12B Tm1 O13B 52.64(18) . . ?
N14A Tm1 O13B 73.67(18) . . ?
O12C Tm1 O13B 152.39(17) . . ?
O11E Tm1 O13C 77.0(2) . . ?
O1D Tm1 O13C 73.93(18) . . ?
O12B Tm1 O13C 140.46(19) . . ?
N14A Tm1 O13C 126.83(17) . . ?
O12C Tm1 O13C 52.51(17) . . ?
O13B Tm1 O13C 139.2(2) . . ?
O11E Tm1 N1A 149.7(2) . . ?
O1D Tm1 N1A 83.1(2) . . ?
O12B Tm1 N1A 74.34(17) . . ?
N14A Tm1 N1A 127.86(18) . . ?
O12C Tm1 N1A 80.28(16) . . ?
O13B Tm1 N1A 124.61(17) . . ?
O13C Tm1 N1A 74.09(18) . . ?
O11E Tm1 N8A 139.9(2) . . ?
O1D Tm1 N8A 139.60(19) . . ?
O12B Tm1 N8A 72.18(17) . . ?
N14A Tm1 N8A 65.62(16) . . ?
O12C Tm1 N8A 70.28(16) . . ?
O13B Tm1 N8A 108.53(18) . . ?
O13C Tm1 N8A 112.14(17) . . ?
N1A Tm1 N8A 62.26(17) . . ?
O11E Tm1 N1B 100.8(3) . . ?
O1D Tm1 N1B 76.05(19) . . ?
O12B Tm1 N1B 25.97(19) . . ?
N14A Tm1 N1B 80.73(17) . . ?
O12C Tm1 N1B 157.00(18) . . ?
O13B Tm1 N1B 26.74(19) . . ?
O13C Tm1 N1B 149.84(18) . . ?
N1A Tm1 N1B 99.59(18) . . ?
N8A Tm1 N1B 89.15(18) . . ?
O11E Tm1 N1C 82.8(2) . . ?
O1D Tm1 N1C 100.26(19) . . ?
O12B Tm1 N1C 149.58(17) . . ?
N14A Tm1 N1C 104.56(17) . . ?
O12C Tm1 N1C 26.13(17) . . ?
O13B Tm1 N1C 156.71(19) . . ?
O13C Tm1 N1C 26.39(17) . . ?
N1A Tm1 N1C 75.40(16) . . ?
N8A Tm1 N1C 90.96(16) . . ?
N1B Tm1 N1C 174.22(16) . . ?
C2A N1A C6A 119.2(5) . . ?
C2A N1A Tm1 123.3(4) . . ?
C6A N1A Tm1 117.3(5) . . ?
N1A C2A N7A 117.2(5) . . ?
N1A C2A C3A 121.7(6) . . ?
N7A C2A C3A 121.1(6) . . ?
C4A C3A C2A 117.6(7) . . ?
C4A C3A H3A 121.2 . . ?
C2A C3A H3A 121.2 . . ?
C5A C4A C3A 120.6(7) . . ?
C5A C4A H4A 119.7 . . ?
C3A C4A H4A 119.7 . . ?
C4A C5A C6A 118.5(7) . . ?
C4A C5A H5A 120.7 . . ?
C6A C5A H5A 120.7 . . ?
N1A C6A C5A 122.4(7) . . ?
N1A C6A H6A 118.8 . . ?
C5A C6A H6A 118.8 . . ?
N8A N7A C2A 116.4(5) . . ?
N8A N7A C71A 119.5(5) . . ?
C2A N7A C71A 124.0(5) . . ?
N7A C71A H71C 109.5 . . ?
N7A C71A H71B 109.5 . . ?
H71C C71A H71B 109.5 . . ?
N7A C71A H71A 109.5 . . ?
H71C C71A H71A 109.5 . . ?
H71B C71A H71A 109.5 . . ?
C9A N8A N7A 121.4(5) . . ?
C9A N8A Tm1 118.0(4) . . ?
N7A N8A Tm1 120.5(4) . . ?
N8A C9A C10A 115.6(5) . . ?
N8A C9A H9A 122.2 . . ?
C10A C9A H9A 122.2 . . ?
N14A C10A N11A 112.1(6) . . ?
N14A C10A C9A 121.9(5) . . ?
N11A C10A C9A 126.0(6) . . ?
C10A N11A C12A 106.6(6) . . ?
C10A N11A C11A 126.8(6) . . ?
C12A N11A C11A 126.5(6) . . ?
N11A C11A H11C 109.5 . . ?
N11A C11A H11B 109.5 . . ?
H11C C11A H11B 109.5 . . ?
N11A C11A H11A 109.5 . . ?
H11C C11A H11A 109.5 . . ?
H11B C11A H11A 109.5 . . ?
N11A C12A C13A 106.7(6) . . ?
N11A C12A H12A 126.7 . . ?
C13A C12A H12A 126.7 . . ?
C12A C13A N14A 108.9(7) . . ?
C12A C13A H13A 125.6 . . ?
N14A C13A H13A 125.6 . . ?
C10A N14A C13A 105.7(6) . . ?
C10A N14A Tm1 118.9(4) . . ?
C13A N14A Tm1 135.4(5) . . ?
O11B N1B O12B 122.7(8) . . ?
O11B N1B O13B 122.8(7) . . ?
O12B N1B O13B 114.5(5) . . ?
O11B N1B Tm1 175.3(7) . . ?
O12B N1B Tm1 54.6(3) . . ?
O13B N1B Tm1 60.1(3) . . ?
N1B O12B Tm1 99.4(4) . . ?
N1B O13B Tm1 93.1(4) . . ?
O11C N1C O12C 121.1(7) . . ?
O11C N1C O13C 122.3(7) . . ?
O12C N1C O13C 116.7(5) . . ?
O11C N1C Tm1 177.6(5) . . ?
O12C N1C Tm1 57.2(3) . . ?
O13C N1C Tm1 59.5(3) . . ?
N1C O12C Tm1 96.6(4) . . ?
N1C O13C Tm1 94.2(4) . . ?
C1D O1D Tm1 135.2(7) . . ?
C1D O1D H1D 109.6 . . ?
Tm1 O1D H1D 114.8 . . ?
O1D C1D H11D 109.5 . . ?
O1D C1D H12D 109.5 . . ?
H11D C1D H12D 109.5 . . ?
O1D C1D H13D 109.5 . . ?
H11D C1D H13D 109.5 . . ?
H12D C1D H13D 109.5 . . ?
O11E N1E O12E 127.3(9) . . ?
O11E N1E O13E 116.9(8) . . ?
O12E N1E O13E 115.8(8) . . ?
N1E O11E Tm1 146.8(6) . . ?
C2F N1F C6F 117.2(9) . . ?
N1F C2F C3F 122.9(9) . . ?
N1F C2F N7F 115.8(8) . . ?
C3F C2F N7F 121.4(7) . . ?
C4F C3F C2F 118.1(9) . . ?
C4F C3F H3F 121.0 . . ?
C2F C3F H3F 121.0 . . ?
C3F C4F C5F 119.3(11) . . ?
C3F C4F H4F 120.3 . . ?
C5F C4F H4F 120.3 . . ?
C6F C5F C4F 118.3(10) . . ?
C6F C5F H5F 120.9 . . ?
C4F C5F H5F 120.9 . . ?
N1F C6F C5F 124.2(10) . . ?
N1F C6F H6F 117.9 . . ?
C5F C6F H6F 117.9 . . ?
N8F N7F C2F 116.1(7) . . ?
N8F N7F C71F 120.8(7) . . ?
C2F N7F C71F 123.1(7) . . ?
N7F C71F H73F 109.5 . . ?
N7F C71F H72F 109.5 . . ?
H73F C71F H72F 109.5 . . ?
N7F C71F H71F 109.5 . . ?
H73F C71F H71F 109.5 . . ?
H72F C71F H71F 109.5 . . ?
C9F N8F N7F 119.5(7) . . ?
N8F C9F C10F 115.5(7) . . ?
N8F C9F H9F 122.2 . . ?
C10F C9F H9F 122.2 . . ?
N14F C10F N11F 108.6(7) . . ?
N14F C10F C9F 126.1(7) . . ?
N11F C10F C9F 125.3(8) . . ?
C10F N11F C12F 108.1(8) . . ?
C10F N11F C11F 126.3(9) . . ?
C12F N11F C11F 125.6(8) . . ?
N11F C11F H11F 109.5 . . ?
N11F C11F H11G 109.5 . . ?
H11F C11F H11G 109.5 . . ?
N11F C11F H11H 109.5 . . ?
H11F C11F H11H 109.5 . . ?
H11G C11F H11H 109.5 . . ?
C13F C12F N11F 106.9(8) . . ?
C13F C12F H12F 126.5 . . ?
N11F C12F H12F 126.5 . . ?
C12F C13F N14F 106.6(8) . . ?
C12F C13F H13F 126.7 . . ?
N14F C13F H13F 126.7 . . ?
C10F N14F C13F 109.7(7) . . ?
C10F N14F H14F 125.1 . . ?
C13F N14F H14F 125.1 . . ?
O11G N1G O12G 118.5(8) . . ?
O11G N1G O13G 119.6(8) . . ?
O12G N1G O13G 121.9(8) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6A N1A C2A N7A -179.3(5) . . . . ?
Tm1 N1A C2A N7A 5.8(7) . . . . ?
C6A N1A C2A C3A -0.1(8) . . . . ?
Tm1 N1A C2A C3A -175.0(4) . . . . ?
N1A C2A C3A C4A 0.7(9) . . . . ?
N7A C2A C3A C4A 179.9(6) . . . . ?
C2A C3A C4A C5A 0.0(10) . . . . ?
C3A C4A C5A C6A -1.2(10) . . . . ?
C2A N1A C6A C5A -1.2(9) . . . . ?
Tm1 N1A C6A C5A 174.0(5) . . . . ?
C4A C5A C6A N1A 1.8(10) . . . . ?
N1A C2A N7A N8A -4.2(8) . . . . ?
C3A C2A N7A N8A 176.6(5) . . . . ?
N1A C2A N7A C71A 175.3(6) . . . . ?
C3A C2A N7A C71A -3.9(9) . . . . ?
C2A N7A N8A C9A -177.4(5) . . . . ?
C71A N7A N8A C9A 3.1(8) . . . . ?
C2A N7A N8A Tm1 0.9(6) . . . . ?
C71A N7A N8A Tm1 -178.6(5) . . . . ?
N7A N8A C9A C10A -179.2(5) . . . . ?
Tm1 N8A C9A C10A 2.5(7) . . . . ?
N8A C9A C10A N14A -1.7(8) . . . . ?
N8A C9A C10A N11A 178.9(6) . . . . ?
N14A C10A N11A C12A 0.8(7) . . . . ?
C9A C10A N11A C12A -179.7(6) . . . . ?
N14A C10A N11A C11A 177.9(6) . . . . ?
C9A C10A N11A C11A -2.7(10) . . . . ?
C10A N11A C12A C13A -0.6(7) . . . . ?
C11A N11A C12A C13A -177.7(7) . . . . ?
N11A C12A C13A N14A 0.3(8) . . . . ?
N11A C10A N14A C13A -0.6(7) . . . . ?
C9A C10A N14A C13A 179.9(6) . . . . ?
N11A C10A N14A Tm1 179.3(4) . . . . ?
C9A C10A N14A Tm1 -0.1(7) . . . . ?
C12A C13A N14A C10A 0.2(7) . . . . ?
C12A C13A N14A Tm1 -179.8(4) . . . . ?
O11B N1B O12B Tm1 175.3(7) . . . . ?
O13B N1B O12B Tm1 -5.2(7) . . . . ?
O11B N1B O13B Tm1 -175.6(7) . . . . ?
O12B N1B O13B Tm1 4.9(6) . . . . ?
O11C N1C O12C Tm1 178.0(6) . . . . ?
O13C N1C O12C Tm1 -1.3(6) . . . . ?
O11C N1C O13C Tm1 -178.0(6) . . . . ?
O12C N1C O13C Tm1 1.2(6) . . . . ?
O12E N1E O11E Tm1 -121.7(14) . . . . ?
O13E N1E O11E Tm1 58.2(14) . . . . ?
C6F N1F C2F C3F -0.7(14) . . . . ?
C6F N1F C2F N7F 179.0(8) . . . . ?
N1F C2F C3F C4F 2.1(14) . . . . ?
N7F C2F C3F C4F -177.6(9) . . . . ?
C2F C3F C4F C5F -1.6(16) . . . . ?
C3F C4F C5F C6F -0.3(18) . . . . ?
C2F N1F C6F C5F -1.3(17) . . . . ?
C4F C5F C6F N1F 1.8(19) . . . . ?
N1F C2F N7F N8F 178.5(7) . . . . ?
C3F C2F N7F N8F -1.8(12) . . . . ?
N1F C2F N7F C71F -2.8(12) . . . . ?
C3F C2F N7F C71F 176.9(9) . . . . ?
C2F N7F N8F C9F 179.7(7) . . . . ?
C71F N7F N8F C9F 1.0(12) . . . . ?
N7F N8F C9F C10F -178.6(7) . . . . ?
N8F C9F C10F N14F 0.5(12) . . . . ?
N8F C9F C10F N11F 178.4(8) . . . . ?
N14F C10F N11F C12F 0.4(10) . . . . ?
C9F C10F N11F C12F -177.7(8) . . . . ?
N14F C10F N11F C11F -178.5(9) . . . . ?
C9F C10F N11F C11F 3.3(14) . . . . ?
C10F N11F C12F C13F 0.2(10) . . . . ?
C11F N11F C12F C13F 179.1(10) . . . . ?
N11F C12F C13F N14F -0.7(10) . . . . ?
N11F C10F N14F C13F -0.9(9) . . . . ?
C9F C10F N14F C13F 177.3(8) . . . . ?
C12F C13F N14F C10F 1.0(10) . . . . ?

_refine_diff_density_max         1.723
_refine_diff_density_min         -3.092
_refine_diff_density_rms         0.149

_shelxl_version_number           2013-4

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_08
_database_code_depnum_ccdc_archive 'CCDC 1052308'
_audit_update_record             
;
2015-11-06 deposited with the CCDC.	2024-07-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C25 H34 Dy F3 N10 O5 S, 2(C F3 O3 S)'
_chemical_formula_sum            'C27 H34 Dy F9 N10 O11 S3'
_chemical_formula_weight         1104.32

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Dy Dy -0.1892 4.4098 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   10.9170(3)
_cell_length_b                   14.9827(3)
_cell_length_c                   26.8953(10)
_cell_angle_alpha                90
_cell_angle_beta                 100.184(3)
_cell_angle_gamma                90
_cell_volume                     4329.9(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(1)
_cell_measurement_reflns_used    9243
_cell_measurement_theta_min      3.1090
_cell_measurement_theta_max      27.9670

_exptl_crystal_description       plate
_exptl_crystal_colour            pale-yellow
_exptl_crystal_density_diffrn    1.694
_exptl_crystal_F_000             2196
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.1
_exptl_absorpt_coefficient_mu    1.972
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.80742
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(1)
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Eos
_diffrn_detector_area_resol_mean 16.1544
_diffrn_measurement_method       ω-scan
_diffrn_reflns_number            38766
_diffrn_reflns_av_unetI/netI     0.0795
_diffrn_reflns_av_R_equivalents  0.0808
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         2.826
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             7596
_reflns_number_gt                5550
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlis Pro (Agilent Technologies (2011))'
_computing_cell_refinement       'CrysAlis Pro (Agilent Technologies (2011))'
_computing_data_reduction        'CrysAlis Pro (Agilent Technologies (2011))'
_computing_structure_solution    'SIR92 (Altomare et al., 1993)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Mercury (MacRae et al., 2009)'
_computing_publication_material  'SHELXL-2013 (Sheldrick, 2013)'

_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0500P)²+2.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7596
_refine_ls_number_parameters     558
_refine_ls_number_restraints     126
_refine_ls_R_factor_all          0.1176
_refine_ls_R_factor_gt           0.0867
_refine_ls_wR_factor_ref         0.1831
_refine_ls_wR_factor_gt          0.1764
_refine_ls_goodness_of_fit_ref   1.711
_refine_ls_restrained_S_all      1.763
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

# SQUEEZE RESULTS (APPEND TO CIF)
# Note: Data are Listed for all Voids in the P1 Unit Cell
# i.e. Centre of Gravity, Solvent Accessible Volume,
# Recovered number of Electrons in the Void and
# Details about the Squeezed Material
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.000 1.000 0.500 245 70 ' '
2 0.500 0.500 0.000 245 70 ' '
_platon_squeeze_details          
;
;

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Dy1 Dy 0.10075(4) 0.17855(3) 0.15117(2) 0.01775(17) Uani 1 1 d . . . . .
N1A N -0.0742(7) 0.1886(6) 0.0754(3) 0.021(2) Uani 1 1 d . . . . .
C2A C -0.1921(10) 0.1662(7) 0.0771(4) 0.027(3) Uani 1 1 d . . . . .
C3A C -0.2887(10) 0.1804(9) 0.0370(4) 0.035(3) Uani 1 1 d . . . . .
H3A H -0.3709 0.1613 0.0386 0.043 Uiso 1 1 calc R U . . .
C4A C -0.2621(11) 0.2235(11) -0.0057(5) 0.051(4) Uani 1 1 d . . . . .
H4A H -0.3265 0.2362 -0.0334 0.061 Uiso 1 1 calc R U . . .
C5A C -0.1411(12) 0.2473(11) -0.0072(5) 0.056(4) Uani 1 1 d . . . . .
H5A H -0.1204 0.2767 -0.0359 0.067 Uiso 1 1 calc R U . . .
C6A C -0.0528(10) 0.2280(8) 0.0330(5) 0.030(3) Uani 1 1 d . . . . .
H6A H 0.0307 0.2435 0.0312 0.036 Uiso 1 1 calc R U . . .
N7A N -0.2169(7) 0.1263(6) 0.1215(3) 0.021(2) Uani 1 1 d . . . . .
C71A C -0.3362(9) 0.0894(8) 0.1263(5) 0.037(3) Uani 1 1 d . . . . .
H71A H -0.3241 0.0320 0.1439 0.055 Uiso 1 1 calc R U . . .
H71B H -0.3861 0.0804 0.0926 0.055 Uiso 1 1 calc R U . . .
H71C H -0.3796 0.1306 0.1455 0.055 Uiso 1 1 calc R U . . .
N8A N -0.1197(7) 0.1267(5) 0.1617(3) 0.019(2) Uani 1 1 d . . . . .
C9A C -0.1377(9) 0.0980(6) 0.2040(5) 0.021(3) Uani 1 1 d . . . . .
H9A H -0.2163 0.0759 0.2089 0.026 Uiso 1 1 calc R U . . .
C10A C -0.0310(9) 0.1010(7) 0.2445(4) 0.018(2) Uani 1 1 d . . . . .
N11A N -0.0280(8) 0.0778(6) 0.2929(3) 0.020(2) Uani 1 1 d . . . . .
C11A C -0.1322(9) 0.0457(8) 0.3155(5) 0.031(3) Uani 1 1 d . . . . .
H11A H -0.1913 0.0946 0.3168 0.047 Uiso 1 1 calc R U . . .
H11B H -0.1011 0.0243 0.3498 0.047 Uiso 1 1 calc R U . . .
H11C H -0.1741 -0.0032 0.2951 0.047 Uiso 1 1 calc R U . . .
C12A C 0.0910(10) 0.0907(7) 0.3181(5) 0.027(3) Uani 1 1 d . . . . .
H12A H 0.1212 0.0794 0.3529 0.032 Uiso 1 1 calc R U . . .
C13A C 0.1569(10) 0.1223(7) 0.2842(4) 0.019(2) Uani 1 1 d . . . . .
H13A H 0.2427 0.1375 0.2914 0.023 Uiso 1 1 calc R U . . .
N14A N 0.0819(7) 0.1296(5) 0.2375(3) 0.017(2) Uani 1 1 d . . . . .
N1B N 0.2847(8) 0.2521(5) 0.2068(3) 0.021(2) Uani 1 1 d . . . . .
C2B C 0.3929(9) 0.2118(7) 0.2236(4) 0.022(3) Uani 1 1 d . . . . .
C3B C 0.4993(10) 0.2557(7) 0.2488(5) 0.031(3) Uani 1 1 d . . . . .
H3B H 0.5751 0.2247 0.2599 0.038 Uiso 1 1 calc R U . . .
C4B C 0.4890(11) 0.3453(8) 0.2566(5) 0.038(3) Uani 1 1 d . . . . .
H4B H 0.5596 0.3778 0.2727 0.046 Uiso 1 1 calc R U . . .
C5B C 0.3764(10) 0.3897(7) 0.2414(4) 0.027(3) Uani 1 1 d . . . . .
H5B H 0.3673 0.4511 0.2487 0.033 Uiso 1 1 calc R U . . .
C6B C 0.2799(10) 0.3417(6) 0.2155(4) 0.020(2) Uani 1 1 d . . . . .
H6B H 0.2047 0.3724 0.2027 0.024 Uiso 1 1 calc R U . . .
N7B N 0.3967(7) 0.1199(6) 0.2147(3) 0.019(2) Uani 1 1 d . . . . .
C71B C 0.4998(9) 0.0618(7) 0.2357(4) 0.025(3) Uani 1 1 d . . . . .
H71D H 0.4701 0.0155 0.2564 0.038 Uiso 1 1 calc R U . . .
H71E H 0.5649 0.0970 0.2566 0.038 Uiso 1 1 calc R U . . .
H71F H 0.5337 0.0336 0.2082 0.038 Uiso 1 1 calc R U . . .
N8B N 0.2910(7) 0.0832(6) 0.1879(4) 0.022(2) Uani 1 1 d . . . . .
C9B C 0.2893(10) -0.0008(7) 0.1777(4) 0.024(3) Uani 1 1 d . . . . .
H9B H 0.3589 -0.0386 0.1883 0.029 Uiso 1 1 calc R U . . .
C10B C 0.1727(11) -0.0331(7) 0.1489(4) 0.027(3) Uani 1 1 d . . . . .
N11B N 0.1489(9) -0.1205(6) 0.1357(4) 0.030(2) Uani 1 1 d . . . . .
C11B C 0.2371(11) -0.1950(7) 0.1446(5) 0.040(3) Uani 1 1 d . . . . .
H11D H 0.3076 -0.1832 0.1275 0.060 Uiso 1 1 calc R U . . .
H11E H 0.1955 -0.2502 0.1314 0.060 Uiso 1 1 calc R U . . .
H11F H 0.2673 -0.2013 0.1810 0.060 Uiso 1 1 calc R U . . .
C12B C 0.0278(10) -0.1246(7) 0.1119(5) 0.034(3) Uani 1 1 d . . . . .
H12B H -0.0171 -0.1760 0.0984 0.041 Uiso 1 1 calc R U . . .
C13B C -0.0149(10) -0.0387(8) 0.1118(5) 0.033(3) Uani 1 1 d . . . . .
H13B H -0.0971 -0.0210 0.0974 0.040 Uiso 1 1 calc R U . . .
N14B N 0.0729(8) 0.0172(6) 0.1345(4) 0.024(2) Uani 1 1 d . . . . .
S1C S 0.3160(4) 0.1229(3) 0.0624(2) 0.0883(18) Uani 1 1 d D U . . .
O11C O 0.3651(10) 0.0305(6) 0.0806(5) 0.100(4) Uani 1 1 d D U . . .
O12C O 0.4101(6) 0.1794(5) 0.0554(3) 0.046(2) Uani 1 1 d D U . . .
O13C O 0.2195(6) 0.1530(5) 0.0872(3) 0.0289(19) Uani 1 1 d D U . . .
C1C C 0.242(2) 0.0781(17) 0.0049(9) 0.111(7) Uani 1 1 d . U . . .
F11C F 0.1977(9) 0.1700(7) -0.0153(4) 0.090(3) Uani 1 1 d . U . . .
F12C F 0.3193(8) 0.0380(7) -0.0205(4) 0.085(3) Uani 1 1 d . U . . .
F13C F 0.1550(9) 0.0168(7) 0.0109(4) 0.090(3) Uani 1 1 d . U . . .
O1D O 0.1309(7) 0.3213(5) 0.1113(3) 0.0277(18) Uani 1 1 d . . . . .
H1D H 0.1188 0.3551 0.1349 0.036 Uiso 1 1 calc DR U . . .
C1D C 0.2288(12) 0.3562(9) 0.0886(6) 0.046(4) Uani 1 1 d . . . . .
H1D1 H 0.2331 0.4211 0.0932 0.070 Uiso 1 1 calc R U . . .
H1D2 H 0.2128 0.3423 0.0524 0.070 Uiso 1 1 calc R U . . .
H1D3 H 0.3079 0.3294 0.1045 0.070 Uiso 1 1 calc R U . . .
O1E O -0.0093(6) 0.2962(4) 0.1858(3) 0.0226(18) Uani 1 1 d . . . . .
H1E H 0.0021 0.3027 0.2173 0.029 Uiso 1 1 calc DR U . . .
C1E C -0.1357(14) 0.3398(10) 0.1616(7) 0.069(5) Uani 1 1 d . U . . .
H1E1 H -0.1360 0.4026 0.1718 0.104 Uiso 1 1 calc R U . . .
H1E2 H -0.2041 0.3083 0.1732 0.104 Uiso 1 1 calc R U . . .
H1E3 H -0.1462 0.3360 0.1248 0.104 Uiso 1 1 calc R U . . .
S1F S 0.4425(4) 0.0686(3) 0.37472(15) 0.0571(11) Uani 1 1 d D U . . .
O11F O 0.3493(8) 0.0852(7) 0.4057(4) 0.070(3) Uani 1 1 d D U . . .
O12F O 0.4667(8) 0.1418(5) 0.3440(3) 0.046(2) Uani 1 1 d D U . . .
O13F O 0.4350(7) -0.0155(4) 0.3504(3) 0.035(2) Uani 1 1 d D U . . .
C1F C 0.5818(10) 0.0610(7) 0.4212(4) 0.091(6) Uani 1 1 d D U . . .
F11F F 0.5973(8) 0.1353(6) 0.4501(3) 0.079(3) Uani 1 1 d D U . . .
F12F F 0.5704(8) -0.0068(6) 0.4536(3) 0.088(3) Uani 1 1 d D U . . .
F13F F 0.6769(8) 0.0477(6) 0.3952(4) 0.085(3) Uani 1 1 d D U . . .
S1G S 0.8600(2) 0.32939(19) 0.29550(11) 0.0252(6) Uani 1 1 d . . . . .
O11G O 0.7934(7) 0.2522(5) 0.2750(3) 0.032(2) Uani 1 1 d . . . . .
O12G O 0.9856(6) 0.3350(5) 0.2841(3) 0.0292(19) Uani 1 1 d . . . . .
O13G O 0.7931(6) 0.4118(5) 0.2893(3) 0.030(2) Uani 1 1 d . . . . .
C1G C 0.8869(11) 0.3107(9) 0.3630(5) 0.037(3) Uani 1 1 d . . . . .
F11G F 0.7792(7) 0.3061(5) 0.3799(3) 0.056(2) Uani 1 1 d . . . . .
F12G F 0.9524(7) 0.3770(5) 0.3877(3) 0.046(2) Uani 1 1 d . . . . .
F13G F 0.9492(7) 0.2351(5) 0.3758(3) 0.0455(19) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Dy1 O13C 2.360(6) . ?
Dy1 N14B 2.467(8) . ?
Dy1 N14A 2.479(9) . ?
Dy1 N1B 2.534(8) . ?
Dy1 N1A 2.540(8) . ?
Dy1 N8B 2.570(8) . ?
Dy1 N8A 2.591(8) . ?
N1A C6A 1.340(14) . ?
N1A C2A 1.340(13) . ?
C2A C3A 1.385(14) . ?
C2A N7A 1.404(14) . ?
C3A C4A 1.392(17) . ?
C4A C5A 1.375(17) . ?
C5A C6A 1.347(17) . ?
N7A N8A 1.373(11) . ?
N7A C71A 1.442(13) . ?
N8A C9A 1.264(13) . ?
C9A C10A 1.450(14) . ?
C10A N11A 1.341(13) . ?
C10A N14A 1.349(12) . ?
N11A C12A 1.368(12) . ?
N11A C11A 1.463(13) . ?
C12A C13A 1.343(15) . ?
C13A N14A 1.377(13) . ?
N1B C2B 1.332(13) . ?
N1B C6B 1.366(12) . ?
C2B N7B 1.400(13) . ?
C2B C3B 1.402(14) . ?
C3B C4B 1.366(16) . ?
C4B C5B 1.394(15) . ?
C5B C6B 1.361(14) . ?
N7B N8B 1.362(11) . ?
N7B C71B 1.456(12) . ?
N8B C9B 1.287(13) . ?
C9B C10B 1.452(15) . ?
C10B N14B 1.326(13) . ?
C10B N11B 1.370(13) . ?
N11B C12B 1.364(13) . ?
N11B C11B 1.465(13) . ?
C12B C13B 1.369(15) . ?
C13B N14B 1.337(13) . ?
S1C O12C 1.369(6) . ?
S1C O13C 1.418(6) . ?
S1C O11C 1.533(7) . ?
S1C C1C 1.75(2) . ?
C1C F12C 1.32(2) . ?
C1C F13C 1.35(2) . ?
C1C F11C 1.53(2) . ?
O1D C1D 1.420(13) . ?
O1E C1E 1.561(17) . ?
S1F O13F 1.416(6) . ?
S1F O12F 1.425(7) . ?
S1F O11F 1.447(7) . ?
S1F C1F 1.793(11) . ?
C1F F11F 1.350(9) . ?
C1F F12F 1.359(9) . ?
C1F F13F 1.367(9) . ?
S1G O11G 1.424(8) . ?
S1G O13G 1.429(7) . ?
S1G O12G 1.459(7) . ?
S1G C1G 1.809(13) . ?
C1G F12G 1.331(14) . ?
C1G F11G 1.334(13) . ?
C1G F13G 1.335(13) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O13C Dy1 N14B 77.0(3) . . ?
O13C Dy1 N14A 141.4(3) . . ?
N14B Dy1 N14A 81.5(3) . . ?
O13C Dy1 N1B 91.2(3) . . ?
N14B Dy1 N1B 126.3(3) . . ?
N14A Dy1 N1B 76.3(3) . . ?
O13C Dy1 N1A 81.7(3) . . ?
N14B Dy1 N1A 82.0(3) . . ?
N14A Dy1 N1A 126.5(3) . . ?
N1B Dy1 N1A 148.5(3) . . ?
O13C Dy1 N8B 71.3(3) . . ?
N14B Dy1 N8B 65.8(3) . . ?
N14A Dy1 N8B 70.8(3) . . ?
N1B Dy1 N8B 60.8(3) . . ?
N1A Dy1 N8B 141.6(3) . . ?
O13C Dy1 N8A 132.1(3) . . ?
N14B Dy1 N8A 68.9(3) . . ?
N14A Dy1 N8A 65.0(3) . . ?
N1B Dy1 N8A 136.1(3) . . ?
N1A Dy1 N8A 61.6(3) . . ?
N8B Dy1 N8A 119.7(3) . . ?
C6A N1A C2A 117.0(9) . . ?
C6A N1A Dy1 119.3(6) . . ?
C2A N1A Dy1 123.2(7) . . ?
N1A C2A C3A 122.5(11) . . ?
N1A C2A N7A 117.9(9) . . ?
C3A C2A N7A 119.6(10) . . ?
C2A C3A C4A 118.2(11) . . ?
C5A C4A C3A 119.1(12) . . ?
C6A C5A C4A 118.4(13) . . ?
N1A C6A C5A 124.7(11) . . ?
N8A N7A C2A 115.4(8) . . ?
N8A N7A C71A 121.1(9) . . ?
C2A N7A C71A 123.5(9) . . ?
C9A N8A N7A 119.0(9) . . ?
C9A N8A Dy1 119.7(7) . . ?
N7A N8A Dy1 121.3(6) . . ?
N8A C9A C10A 115.8(9) . . ?
N11A C10A N14A 110.6(9) . . ?
N11A C10A C9A 127.0(9) . . ?
N14A C10A C9A 122.5(10) . . ?
C10A N11A C12A 107.6(9) . . ?
C10A N11A C11A 126.9(9) . . ?
C12A N11A C11A 125.5(10) . . ?
C13A C12A N11A 106.8(10) . . ?
C12A C13A N14A 110.1(9) . . ?
C10A N14A C13A 104.9(9) . . ?
C10A N14A Dy1 117.0(6) . . ?
C13A N14A Dy1 138.0(7) . . ?
C2B N1B C6B 116.5(9) . . ?
C2B N1B Dy1 124.4(7) . . ?
C6B N1B Dy1 118.5(7) . . ?
N1B C2B N7B 116.0(9) . . ?
N1B C2B C3B 124.1(10) . . ?
N7B C2B C3B 119.8(10) . . ?
C4B C3B C2B 116.8(11) . . ?
C3B C4B C5B 121.1(11) . . ?
C6B C5B C4B 117.4(10) . . ?
C5B C6B N1B 123.9(10) . . ?
N8B N7B C2B 116.1(8) . . ?
N8B N7B C71B 119.2(8) . . ?
C2B N7B C71B 124.5(9) . . ?
C9B N8B N7B 119.1(9) . . ?
C9B N8B Dy1 118.7(7) . . ?
N7B N8B Dy1 122.0(6) . . ?
N8B C9B C10B 114.8(10) . . ?
N14B C10B N11B 111.1(10) . . ?
N14B C10B C9B 124.3(10) . . ?
N11B C10B C9B 124.5(10) . . ?
C12B N11B C10B 106.8(9) . . ?
C12B N11B C11B 126.7(9) . . ?
C10B N11B C11B 126.6(9) . . ?
N11B C12B C13B 105.1(9) . . ?
N14B C13B C12B 111.9(10) . . ?
C10B N14B C13B 105.2(9) . . ?
C10B N14B Dy1 115.8(7) . . ?
C13B N14B Dy1 138.9(7) . . ?
O12C S1C O13C 120.4(5) . . ?
O12C S1C O11C 112.0(6) . . ?
O13C S1C O11C 112.6(6) . . ?
O12C S1C C1C 111.0(9) . . ?
O13C S1C C1C 105.8(9) . . ?
O11C S1C C1C 91.0(10) . . ?
S1C O13C Dy1 160.9(5) . . ?
F12C C1C F13C 106.2(19) . . ?
F12C C1C F11C 114.7(18) . . ?
F13C C1C F11C 118.3(18) . . ?
F12C C1C S1C 113.0(16) . . ?
F13C C1C S1C 112.4(16) . . ?
F11C C1C S1C 92.0(13) . . ?
O13F S1F O12F 114.7(5) . . ?
O13F S1F O11F 115.5(6) . . ?
O12F S1F O11F 115.0(6) . . ?
O13F S1F C1F 103.8(5) . . ?
O12F S1F C1F 103.4(5) . . ?
O11F S1F C1F 101.8(5) . . ?
F11F C1F F12F 105.4(9) . . ?
F11F C1F F13F 112.7(9) . . ?
F12F C1F F13F 112.5(9) . . ?
F11F C1F S1F 110.7(8) . . ?
F12F C1F S1F 109.4(8) . . ?
F13F C1F S1F 106.2(7) . . ?
O11G S1G O13G 116.1(4) . . ?
O11G S1G O12G 113.6(5) . . ?
O13G S1G O12G 113.9(5) . . ?
O11G S1G C1G 104.1(6) . . ?
O13G S1G C1G 103.8(5) . . ?
O12G S1G C1G 103.2(5) . . ?
F12G C1G F11G 107.3(10) . . ?
F12G C1G F13G 107.4(9) . . ?
F11G C1G F13G 107.9(10) . . ?
F12G C1G S1G 111.3(9) . . ?
F11G C1G S1G 110.7(8) . . ?
F13G C1G S1G 112.0(9) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6A N1A C2A C3A 1.5(16) . . . . ?
Dy1 N1A C2A C3A 173.3(9) . . . . ?
C6A N1A C2A N7A -178.9(10) . . . . ?
Dy1 N1A C2A N7A -7.1(13) . . . . ?
N1A C2A C3A C4A -3.0(19) . . . . ?
N7A C2A C3A C4A 177.4(11) . . . . ?
C2A C3A C4A C5A 2(2) . . . . ?
C3A C4A C5A C6A 0(2) . . . . ?
C2A N1A C6A C5A 0.8(18) . . . . ?
Dy1 N1A C6A C5A -171.3(11) . . . . ?
C4A C5A C6A N1A -2(2) . . . . ?
N1A C2A N7A N8A 9.5(14) . . . . ?
C3A C2A N7A N8A -170.8(10) . . . . ?
N1A C2A N7A C71A -172.4(10) . . . . ?
C3A C2A N7A C71A 7.2(16) . . . . ?
C2A N7A N8A C9A 174.8(9) . . . . ?
C71A N7A N8A C9A -3.4(14) . . . . ?
C2A N7A N8A Dy1 -7.9(11) . . . . ?
C71A N7A N8A Dy1 173.9(8) . . . . ?
N7A N8A C9A C10A -179.7(8) . . . . ?
Dy1 N8A C9A C10A 2.9(12) . . . . ?
N8A C9A C10A N11A 177.2(10) . . . . ?
N8A C9A C10A N14A -2.2(15) . . . . ?
N14A C10A N11A C12A -0.8(11) . . . . ?
C9A C10A N11A C12A 179.8(10) . . . . ?
N14A C10A N11A C11A 178.5(9) . . . . ?
C9A C10A N11A C11A -1.0(17) . . . . ?
C10A N11A C12A C13A 0.6(12) . . . . ?
C11A N11A C12A C13A -178.6(10) . . . . ?
N11A C12A C13A N14A -0.3(12) . . . . ?
N11A C10A N14A C13A 0.6(11) . . . . ?
C9A C10A N14A C13A -179.9(9) . . . . ?
N11A C10A N14A Dy1 -179.2(6) . . . . ?
C9A C10A N14A Dy1 0.3(12) . . . . ?
C12A C13A N14A C10A -0.2(11) . . . . ?
C12A C13A N14A Dy1 179.5(7) . . . . ?
C6B N1B C2B N7B 179.8(9) . . . . ?
Dy1 N1B C2B N7B -8.6(14) . . . . ?
C6B N1B C2B C3B -0.3(17) . . . . ?
Dy1 N1B C2B C3B 171.4(9) . . . . ?
N1B C2B C3B C4B 0.6(19) . . . . ?
N7B C2B C3B C4B -179.5(11) . . . . ?
C2B C3B C4B C5B 1.8(19) . . . . ?
C3B C4B C5B C6B -4.3(19) . . . . ?
C4B C5B C6B N1B 4.7(18) . . . . ?
C2B N1B C6B C5B -2.5(16) . . . . ?
Dy1 N1B C6B C5B -174.7(9) . . . . ?
N1B C2B N7B N8B 2.9(15) . . . . ?
C3B C2B N7B N8B -177.1(10) . . . . ?
N1B C2B N7B C71B -171.3(10) . . . . ?
C3B C2B N7B C71B 8.7(17) . . . . ?
C2B N7B N8B C9B 178.8(10) . . . . ?
C71B N7B N8B C9B -6.6(15) . . . . ?
C2B N7B N8B Dy1 3.7(12) . . . . ?
C71B N7B N8B Dy1 178.2(7) . . . . ?
N7B N8B C9B C10B -179.8(9) . . . . ?
Dy1 N8B C9B C10B -4.5(14) . . . . ?
N8B C9B C10B N14B -1.4(17) . . . . ?
N8B C9B C10B N11B -177.5(11) . . . . ?
N14B C10B N11B C12B -0.3(14) . . . . ?
C9B C10B N11B C12B 176.2(11) . . . . ?
N14B C10B N11B C11B 178.9(11) . . . . ?
C9B C10B N11B C11B -4.5(19) . . . . ?
C10B N11B C12B C13B 0.4(14) . . . . ?
C11B N11B C12B C13B -178.8(12) . . . . ?
N11B C12B C13B N14B -0.4(15) . . . . ?
N11B C10B N14B C13B 0.0(13) . . . . ?
C9B C10B N14B C13B -176.5(11) . . . . ?
N11B C10B N14B Dy1 -176.9(7) . . . . ?
C9B C10B N14B Dy1 6.5(15) . . . . ?
C12B C13B N14B C10B 0.3(14) . . . . ?
C12B C13B N14B Dy1 176.1(9) . . . . ?
O12C S1C O13C Dy1 -98.8(16) . . . . ?
O11C S1C O13C Dy1 36.6(18) . . . . ?
C1C S1C O13C Dy1 134.5(17) . . . . ?
O12C S1C C1C F12C 55(2) . . . . ?
O13C S1C C1C F12C -172.9(15) . . . . ?
O11C S1C C1C F12C -59.1(17) . . . . ?
O12C S1C C1C F13C 175.1(13) . . . . ?
O13C S1C C1C F13C -52.8(18) . . . . ?
O11C S1C C1C F13C 61.0(17) . . . . ?
O12C S1C C1C F11C -63.0(12) . . . . ?
O13C S1C C1C F11C 69.1(11) . . . . ?
O11C S1C C1C F11C -177.1(10) . . . . ?
O13F S1F C1F F11F -176.0(8) . . . . ?
O12F S1F C1F F11F 63.9(9) . . . . ?
O11F S1F C1F F11F -55.8(9) . . . . ?
O13F S1F C1F F12F -60.3(8) . . . . ?
O12F S1F C1F F12F 179.6(8) . . . . ?
O11F S1F C1F F12F 60.0(9) . . . . ?
O13F S1F C1F F13F 61.3(8) . . . . ?
O12F S1F C1F F13F -58.8(8) . . . . ?
O11F S1F C1F F13F -178.4(8) . . . . ?
O11G S1G C1G F12G 178.2(8) . . . . ?
O13G S1G C1G F12G -59.9(9) . . . . ?
O12G S1G C1G F12G 59.3(9) . . . . ?
O11G S1G C1G F11G -62.6(10) . . . . ?
O13G S1G C1G F11G 59.4(10) . . . . ?
O12G S1G C1G F11G 178.5(8) . . . . ?
O11G S1G C1G F13G 57.9(9) . . . . ?
O13G S1G C1G F13G 179.9(8) . . . . ?
O12G S1G C1G F13G -61.0(9) . . . . ?

_refine_diff_density_max         5.127
_refine_diff_density_min         -2.640
_refine_diff_density_rms         0.216

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_17
_database_code_depnum_ccdc_archive 'CCDC 1435584'
_audit_update_record             
;
2015-11-06 deposited with the CCDC.	2024-07-03 downloaded from the CCDC.
;


_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H17 Gd N8 O10, C2 H3 N'
_chemical_formula_sum            'C14 H20 Gd N9 O10'
_chemical_formula_weight         631.64

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Gd Gd -0.1653 3.9035 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.2937(17)
_cell_length_b                   11.3355(15)
_cell_length_c                   13.441(3)
_cell_angle_alpha                110.013(16)
_cell_angle_beta                 107.641(18)
_cell_angle_gamma                92.604(14)
_cell_volume                     1115.7(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    130(1)
_cell_measurement_reflns_used    862
_cell_measurement_theta_min      3.5190
_cell_measurement_theta_max      28.0130

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.880
_exptl_crystal_F_000             622
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_absorpt_coefficient_mu    3.043
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.83214
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.34a (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?

_diffrn_ambient_temperature      130(1)
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Eos
_diffrn_detector_area_resol_mean 16.1544
_diffrn_measurement_method       ω-scan
_diffrn_reflns_number            7965
_diffrn_reflns_av_unetI/netI     0.0410
_diffrn_reflns_av_R_equivalents  0.0240
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.984
_diffrn_reflns_theta_max         28.197
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.840
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.840
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.840
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4601
_reflns_number_gt                4217
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlis Pro (Agilent Technologies (2011))'
_computing_cell_refinement       'CrysAlis Pro (Agilent Technologies (2011))'
_computing_data_reduction        'CrysAlis Pro (Agilent Technologies (2011))'
_computing_structure_solution    'SIR92 (Altomare et al., 1993)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Mercury (MacRae et al., 2009)'
_computing_publication_material  'SHELXL-2013 (Sheldrick, 2013)'

_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0261P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4601
_refine_ls_number_parameters     315
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0276
_refine_ls_R_factor_gt           0.0239
_refine_ls_wR_factor_ref         0.0561
_refine_ls_wR_factor_gt          0.0549
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.046
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Gd1 Gd 0.31089(2) 0.34376(2) 0.74396(2) 0.01163(6) Uani 1 1 d . . . . .
N1A N 0.0373(3) 0.4378(2) 0.6886(2) 0.0138(5) Uani 1 1 d . . . . .
C2A C -0.0222(4) 0.5100(3) 0.7687(3) 0.0177(7) Uani 1 1 d . . . . .
H2A H 0.0452 0.5317 0.8454 0.021 Uiso 1 1 calc R U . . .
C3A C -0.1756(4) 0.5533(3) 0.7440(3) 0.0205(7) Uani 1 1 d . . . . .
H3A H -0.2148 0.6020 0.8025 0.025 Uiso 1 1 calc R U . . .
C4A C -0.2726(4) 0.5248(3) 0.6319(3) 0.0192(7) Uani 1 1 d . . . . .
H4A H -0.3776 0.5561 0.6132 0.023 Uiso 1 1 calc R U . . .
C5A C -0.2167(4) 0.4514(3) 0.5480(3) 0.0167(7) Uani 1 1 d . . . . .
H5A H -0.2812 0.4317 0.4710 0.020 Uiso 1 1 calc R U . . .
C6A C -0.0618(4) 0.4063(3) 0.5790(3) 0.0138(6) Uani 1 1 d . . . . .
N7A N -0.0037(3) 0.3267(3) 0.4971(2) 0.0147(6) Uani 1 1 d . . . . .
C71A C -0.1052(4) 0.2745(3) 0.3769(3) 0.0177(7) Uani 1 1 d . . . . .
H71A H -0.0596 0.3197 0.3382 0.027 Uiso 1 1 calc R U . . .
H71B H -0.2250 0.2851 0.3670 0.027 Uiso 1 1 calc R U . . .
H71C H -0.0990 0.1838 0.3451 0.027 Uiso 1 1 calc R U . . .
N8A N 0.1584(3) 0.3003(2) 0.5345(2) 0.0140(5) Uani 1 1 d . . . . .
C9A C 0.2290(4) 0.2412(3) 0.4627(3) 0.0131(6) Uani 1 1 d . . . . .
H9A H 0.1729 0.2153 0.3838 0.016 Uiso 1 1 calc R U . . .
C10A C 0.3986(4) 0.2171(3) 0.5100(3) 0.0134(6) Uani 1 1 d . . . . .
N11A N 0.4884(3) 0.1462(2) 0.4489(2) 0.0144(5) Uani 1 1 d . . . . .
C11A C 0.4316(4) 0.0815(3) 0.3254(3) 0.0218(7) Uani 1 1 d . . . . .
H11C H 0.3119 0.0398 0.2972 0.033 Uiso 1 1 calc R U . . .
H11B H 0.5039 0.0175 0.3055 0.033 Uiso 1 1 calc R U . . .
H11A H 0.4415 0.1441 0.2914 0.033 Uiso 1 1 calc R U . . .
C12A C 0.6416(4) 0.1447(3) 0.5254(3) 0.0163(7) Uani 1 1 d . . . . .
H12A H 0.7324 0.1033 0.5085 0.020 Uiso 1 1 calc R U . . .
C13A C 0.6386(4) 0.2136(3) 0.6298(3) 0.0166(7) Uani 1 1 d . . . . .
H13A H 0.7281 0.2278 0.6985 0.020 Uiso 1 1 calc R U . . .
N14A N 0.4871(3) 0.2594(2) 0.6208(2) 0.0142(5) Uani 1 1 d . . . . .
N1B N 0.0864(3) 0.0937(3) 0.6491(2) 0.0187(6) Uani 1 1 d . . . . .
O11B O 0.2417(3) 0.1024(2) 0.6553(2) 0.0243(5) Uani 1 1 d . . . . .
O12B O 0.0358(3) 0.1984(2) 0.68788(19) 0.0207(5) Uani 1 1 d . . . . .
O13B O -0.0113(3) -0.0091(2) 0.6067(2) 0.0365(7) Uani 1 1 d . . . . .
N1C N 0.4099(3) 0.6185(3) 0.8037(2) 0.0164(6) Uani 1 1 d . . . . .
O11C O 0.4024(3) 0.5326(2) 0.70937(18) 0.0172(5) Uani 1 1 d . . . . .
O12C O 0.3678(3) 0.5808(2) 0.87159(18) 0.0182(5) Uani 1 1 d . . . . .
O13C O 0.4560(3) 0.7318(2) 0.8248(2) 0.0275(6) Uani 1 1 d . . . . .
N1D N 0.6474(4) 0.3221(3) 0.8935(2) 0.0219(6) Uani 1 1 d . . . . .
O11D O 0.5262(3) 0.2265(2) 0.8413(2) 0.0243(5) Uani 1 1 d . . . . .
O12D O 0.6080(3) 0.4276(2) 0.88535(19) 0.0201(5) Uani 1 1 d . . . . .
O13D O 0.7933(3) 0.3155(3) 0.9468(2) 0.0339(6) Uani 1 1 d . . . . .
O1E O 0.2515(3) 0.3659(2) 0.9129(2) 0.0197(5) Uani 1 1 d . . . . .
H1E H 0.297(4) 0.428(3) 0.969(3) 0.016(10) Uiso 1 1 d . . . . .
C1E C 0.1940(5) 0.2660(4) 0.9441(3) 0.0348(9) Uani 1 1 d . . . . .
H1E3 H 0.1710 0.1839 0.8816 0.052 Uiso 1 1 calc R U . . .
H1E2 H 0.0888 0.2824 0.9616 0.052 Uiso 1 1 calc R U . . .
H1E1 H 0.2833 0.2638 1.0105 0.052 Uiso 1 1 calc R U . . .
N1F N -0.0255(6) -0.1055(4) 0.8430(3) 0.0621(13) Uani 1 1 d . . . . .
C2F C 0.1031(6) -0.0831(4) 0.9111(4) 0.0384(10) Uani 1 1 d . . . . .
C3F C 0.2711(6) -0.0527(5) 0.9988(4) 0.0520(12) Uani 1 1 d . . . . .
H3F3 H 0.3101 0.0396 1.0308 0.078 Uiso 1 1 calc R U . . .
H3F2 H 0.3534 -0.0957 0.9664 0.078 Uiso 1 1 calc R U . . .
H3F1 H 0.2624 -0.0815 1.0583 0.078 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Gd1 O1E 2.400(2) . ?
Gd1 O11C 2.474(2) . ?
Gd1 O12B 2.501(2) . ?
Gd1 O12D 2.510(2) . ?
Gd1 N14A 2.511(2) . ?
Gd1 O11B 2.539(2) . ?
Gd1 N1A 2.564(2) . ?
Gd1 N8A 2.570(3) . ?
Gd1 O12C 2.574(2) . ?
Gd1 O11D 2.580(2) . ?
Gd1 N1C 2.945(3) . ?
Gd1 N1B 2.955(3) . ?
N1A C2A 1.352(4) . ?
N1A C6A 1.362(4) . ?
C2A C3A 1.372(4) . ?
C2A H2A 0.9500 . ?
C3A C4A 1.390(5) . ?
C3A H3A 0.9500 . ?
C4A C5A 1.375(4) . ?
C4A H4A 0.9500 . ?
C5A C6A 1.402(4) . ?
C5A H5A 0.9500 . ?
C6A N7A 1.393(4) . ?
N7A N8A 1.371(3) . ?
N7A C71A 1.464(4) . ?
C71A H71A 0.9800 . ?
C71A H71B 0.9800 . ?
C71A H71C 0.9800 . ?
N8A C9A 1.288(4) . ?
C9A C10A 1.438(4) . ?
C9A H9A 0.9500 . ?
C10A N14A 1.343(4) . ?
C10A N11A 1.360(4) . ?
N11A C12A 1.376(4) . ?
N11A C11A 1.476(4) . ?
C11A H11C 0.9800 . ?
C11A H11B 0.9800 . ?
C11A H11A 0.9800 . ?
C12A C13A 1.361(4) . ?
C12A H12A 0.9500 . ?
C13A N14A 1.368(4) . ?
C13A H13A 0.9500 . ?
N1B O13B 1.233(3) . ?
N1B O11B 1.262(3) . ?
N1B O12B 1.269(3) . ?
N1C O13C 1.232(3) . ?
N1C O12C 1.258(3) . ?
N1C O11C 1.289(3) . ?
N1D O13D 1.225(3) . ?
N1D O11D 1.277(4) . ?
N1D O12D 1.285(3) . ?
O1E C1E 1.444(4) . ?
O1E H1E 0.80(4) . ?
C1E H1E3 0.9800 . ?
C1E H1E2 0.9800 . ?
C1E H1E1 0.9800 . ?
N1F C2F 1.125(5) . ?
C2F C3F 1.460(6) . ?
C3F H3F3 0.9800 . ?
C3F H3F2 0.9800 . ?
C3F H3F1 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1E Gd1 O11C 121.11(8) . . ?
O1E Gd1 O12B 72.64(8) . . ?
O11C Gd1 O12B 136.50(7) . . ?
O1E Gd1 O12D 80.27(8) . . ?
O11C Gd1 O12D 76.80(7) . . ?
O12B Gd1 O12D 145.03(7) . . ?
O1E Gd1 N14A 148.28(8) . . ?
O11C Gd1 N14A 77.25(8) . . ?
O12B Gd1 N14A 113.37(8) . . ?
O12D Gd1 N14A 79.53(8) . . ?
O1E Gd1 O11B 96.78(8) . . ?
O11C Gd1 O11B 142.09(8) . . ?
O12B Gd1 O11B 50.29(7) . . ?
O12D Gd1 O11B 113.68(7) . . ?
N14A Gd1 O11B 69.73(8) . . ?
O1E Gd1 N1A 85.98(8) . . ?
O11C Gd1 N1A 74.88(7) . . ?
O12B Gd1 N1A 64.67(8) . . ?
O12D Gd1 N1A 135.65(8) . . ?
N14A Gd1 N1A 125.31(8) . . ?
O11B Gd1 N1A 109.68(8) . . ?
O1E Gd1 N8A 141.32(8) . . ?
O11C Gd1 N8A 72.72(8) . . ?
O12B Gd1 N8A 74.45(8) . . ?
O12D Gd1 N8A 137.53(7) . . ?
N14A Gd1 N8A 65.51(8) . . ?
O11B Gd1 N8A 76.94(8) . . ?
N1A Gd1 N8A 61.64(8) . . ?
O1E Gd1 O12C 70.26(8) . . ?
O11C Gd1 O12C 50.89(7) . . ?
O12B Gd1 O12C 123.26(7) . . ?
O12D Gd1 O12C 64.35(7) . . ?
N14A Gd1 O12C 120.89(8) . . ?
O11B Gd1 O12C 167.00(7) . . ?
N1A Gd1 O12C 71.31(8) . . ?
N8A Gd1 O12C 113.58(8) . . ?
O1E Gd1 O11D 75.07(8) . . ?
O11C Gd1 O11D 122.65(7) . . ?
O12B Gd1 O11D 100.42(7) . . ?
O12D Gd1 O11D 50.38(7) . . ?
N14A Gd1 O11D 73.21(8) . . ?
O11B Gd1 O11D 64.75(8) . . ?
N1A Gd1 O11D 159.03(8) . . ?
N8A Gd1 O11D 131.11(8) . . ?
O12C Gd1 O11D 109.44(7) . . ?
O1E Gd1 N1C 95.46(8) . . ?
O11C Gd1 N1C 25.69(7) . . ?
O12B Gd1 N1C 135.22(7) . . ?
O12D Gd1 N1C 68.03(7) . . ?
N14A Gd1 N1C 99.31(8) . . ?
O11B Gd1 N1C 167.75(7) . . ?
N1A Gd1 N1C 71.66(8) . . ?
N8A Gd1 N1C 93.73(8) . . ?
O12C Gd1 N1C 25.21(7) . . ?
O11D Gd1 N1C 118.39(7) . . ?
O1E Gd1 N1B 84.58(8) . . ?
O11C Gd1 N1B 146.45(7) . . ?
O12B Gd1 N1B 25.18(7) . . ?
O12D Gd1 N1B 132.64(7) . . ?
N14A Gd1 N1B 91.41(8) . . ?
O11B Gd1 N1B 25.12(7) . . ?
N1A Gd1 N1B 87.00(8) . . ?
N8A Gd1 N1B 73.84(8) . . ?
O12C Gd1 N1B 147.40(7) . . ?
O11D Gd1 N1B 82.41(8) . . ?
N1C Gd1 N1B 158.58(7) . . ?
C2A N1A C6A 117.8(3) . . ?
C2A N1A Gd1 120.2(2) . . ?
C6A N1A Gd1 121.65(19) . . ?
N1A C2A C3A 123.0(3) . . ?
N1A C2A H2A 118.5 . . ?
C3A C2A H2A 118.5 . . ?
C2A C3A C4A 118.8(3) . . ?
C2A C3A H3A 120.6 . . ?
C4A C3A H3A 120.6 . . ?
C5A C4A C3A 120.0(3) . . ?
C5A C4A H4A 120.0 . . ?
C3A C4A H4A 120.0 . . ?
C4A C5A C6A 118.2(3) . . ?
C4A C5A H5A 120.9 . . ?
C6A C5A H5A 120.9 . . ?
N1A C6A N7A 117.4(3) . . ?
N1A C6A C5A 122.1(3) . . ?
N7A C6A C5A 120.4(3) . . ?
N8A N7A C6A 116.2(2) . . ?
N8A N7A C71A 120.5(2) . . ?
C6A N7A C71A 123.2(2) . . ?
N7A C71A H71A 109.5 . . ?
N7A C71A H71B 109.5 . . ?
H71A C71A H71B 109.5 . . ?
N7A C71A H71C 109.5 . . ?
H71A C71A H71C 109.5 . . ?
H71B C71A H71C 109.5 . . ?
C9A N8A N7A 119.6(3) . . ?
C9A N8A Gd1 119.0(2) . . ?
N7A N8A Gd1 121.10(18) . . ?
N8A C9A C10A 115.5(3) . . ?
N8A C9A H9A 122.3 . . ?
C10A C9A H9A 122.3 . . ?
N14A C10A N11A 111.2(3) . . ?
N14A C10A C9A 124.2(3) . . ?
N11A C10A C9A 124.6(3) . . ?
C10A N11A C12A 106.3(3) . . ?
C10A N11A C11A 126.9(3) . . ?
C12A N11A C11A 126.8(3) . . ?
N11A C11A H11C 109.5 . . ?
N11A C11A H11B 109.5 . . ?
H11C C11A H11B 109.5 . . ?
N11A C11A H11A 109.5 . . ?
H11C C11A H11A 109.5 . . ?
H11B C11A H11A 109.5 . . ?
C13A C12A N11A 107.2(3) . . ?
C13A C12A H12A 126.4 . . ?
N11A C12A H12A 126.4 . . ?
C12A C13A N14A 109.7(3) . . ?
C12A C13A H13A 125.1 . . ?
N14A C13A H13A 125.1 . . ?
C10A N14A C13A 105.6(3) . . ?
C10A N14A Gd1 114.22(18) . . ?
C13A N14A Gd1 137.8(2) . . ?
O13B N1B O11B 122.6(3) . . ?
O13B N1B O12B 121.7(3) . . ?
O11B N1B O12B 115.6(3) . . ?
O13B N1B Gd1 177.7(2) . . ?
O11B N1B Gd1 58.68(15) . . ?
O12B N1B Gd1 56.97(14) . . ?
N1B O11B Gd1 96.19(18) . . ?
N1B O12B Gd1 97.85(17) . . ?
O13C N1C O12C 122.5(3) . . ?
O13C N1C O11C 120.6(3) . . ?
O12C N1C O11C 116.9(3) . . ?
O13C N1C Gd1 176.6(2) . . ?
O12C N1C Gd1 60.67(15) . . ?
O11C N1C Gd1 56.29(14) . . ?
N1C O11C Gd1 98.02(16) . . ?
N1C O12C Gd1 94.12(17) . . ?
O13D N1D O11D 123.3(3) . . ?
O13D N1D O12D 121.2(3) . . ?
O11D N1D O12D 115.6(3) . . ?
O13D N1D Gd1 173.0(2) . . ?
O11D N1D Gd1 59.51(15) . . ?
O12D N1D Gd1 56.40(15) . . ?
N1D O11D Gd1 95.25(17) . . ?
N1D O12D Gd1 98.36(18) . . ?
C1E O1E Gd1 127.7(2) . . ?
C1E O1E H1E 109(2) . . ?
Gd1 O1E H1E 119(2) . . ?
O1E C1E H1E3 109.5 . . ?
O1E C1E H1E2 109.5 . . ?
H1E3 C1E H1E2 109.5 . . ?
O1E C1E H1E1 109.5 . . ?
H1E3 C1E H1E1 109.5 . . ?
H1E2 C1E H1E1 109.5 . . ?
N1F C2F C3F 179.1(5) . . ?
C2F C3F H3F3 109.5 . . ?
C2F C3F H3F2 109.5 . . ?
H3F3 C3F H3F2 109.5 . . ?
C2F C3F H3F1 109.5 . . ?
H3F3 C3F H3F1 109.5 . . ?
H3F2 C3F H3F1 109.5 . . ?

_refine_diff_density_max         1.191
_refine_diff_density_min         -0.771
_refine_diff_density_rms         0.106

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_16
_database_code_depnum_ccdc_archive 'CCDC 1435583'
_audit_update_record             
;
2016-01-10 deposited with the CCDC.	2024-07-03 downloaded from the CCDC.
;


_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C11 H15 Eu N8 O10, C H4 O'
_chemical_formula_sum            'C12 H19 Eu N8 O11'
_chemical_formula_weight         603.31

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Eu Eu -0.1578 3.6682 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.1426(4)
_cell_length_b                   10.4679(8)
_cell_length_c                   12.4743(7)
_cell_angle_alpha                98.188(6)
_cell_angle_beta                 97.531(4)
_cell_angle_gamma                100.576(5)
_cell_volume                     1020.95(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    120(1)
_cell_measurement_reflns_used    3575
_cell_measurement_theta_min      3.3990
_cell_measurement_theta_max      27.8100

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.963
_exptl_crystal_F_000             596
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.05
_exptl_absorpt_coefficient_mu    3.144
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.70610
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      120(1)
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Eos
_diffrn_detector_area_resol_mean 16.1544
_diffrn_measurement_method       ω-scan
_diffrn_reflns_number            4237
_diffrn_reflns_av_unetI/netI     0.0405
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.837
_diffrn_reflns_theta_max         28.255
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.840
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.840
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.840
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4237
_reflns_number_gt                3940
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlis Pro (Agilent Technologies (2011))'
_computing_cell_refinement       'CrysAlis Pro (Agilent Technologies (2011))'
_computing_data_reduction        'CrysAlis Pro (Agilent Technologies (2011))'
_computing_structure_solution    'SIR92 (Altomare et al., 1993)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Mercury (MacRae et al., 2009)'
_computing_publication_material  'SHELXL-2013 (Sheldrick, 2013)'

_refine_special_details          
;
 Refined as a 2-component twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0277P)²+5.0296P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4237
_refine_ls_number_parameters     293
_refine_ls_number_restraints     7
_refine_ls_R_factor_all          0.0391
_refine_ls_R_factor_gt           0.0353
_refine_ls_wR_factor_ref         0.0828
_refine_ls_wR_factor_gt          0.0807
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_restrained_S_all      1.081
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Eu1 Eu 0.30069(3) 0.76876(2) 0.28936(2) 0.01533(8) Uani 1 1 d . . . . .
N1A N 0.0470(5) 0.6946(4) 0.3818(3) 0.0174(8) Uani 1 1 d . . . . .
C2A C -0.0139(6) 0.7834(5) 0.4464(4) 0.0212(10) Uani 1 1 d . . . . .
H2A H 0.0434 0.8731 0.4583 0.025 Uiso 1 1 calc R U . . .
C3A C -0.1531(6) 0.7525(5) 0.4958(4) 0.0230(11) Uani 1 1 d . . . . .
H3A H -0.1931 0.8188 0.5391 0.028 Uiso 1 1 calc R U . . .
C4A C -0.2341(6) 0.6201(6) 0.4802(4) 0.0235(11) Uani 1 1 d . . . . .
H4A H -0.3288 0.5944 0.5152 0.028 Uiso 1 1 calc R U . . .
C5A C -0.1771(6) 0.5282(5) 0.4150(4) 0.0207(10) Uani 1 1 d . . . . .
H5A H -0.2314 0.4378 0.4037 0.025 Uiso 1 1 calc R U . . .
C6A C -0.0367(5) 0.5687(5) 0.3645(4) 0.0150(9) Uani 1 1 d . . . . .
N7A N 0.0236(5) 0.4776(4) 0.2954(3) 0.0178(8) Uani 1 1 d . . . . .
C71A C -0.0607(6) 0.3404(5) 0.2633(4) 0.0201(10) Uani 1 1 d . . . . .
H71C H -0.0460 0.3085 0.1881 0.030 Uiso 1 1 calc R U . . .
H71B H -0.1816 0.3317 0.2669 0.030 Uiso 1 1 calc R U . . .
H71A H -0.0115 0.2880 0.3131 0.030 Uiso 1 1 calc R U . . .
N8A N 0.1777(5) 0.5219(4) 0.2668(3) 0.0166(8) Uani 1 1 d . . . . .
C9A C 0.2586(6) 0.4391(5) 0.2218(4) 0.0172(9) Uani 1 1 d . . . . .
H9A H 0.2148 0.3466 0.2074 0.021 Uiso 1 1 calc R U . . .
C10A C 0.4207(6) 0.4965(5) 0.1949(4) 0.0185(10) Uani 1 1 d . . . . .
N11A N 0.5177(5) 0.4287(4) 0.1378(3) 0.0202(9) Uani 1 1 d . . . . .
C11A C 0.4795(7) 0.2874(5) 0.0948(5) 0.0290(12) Uani 1 1 d . . . . .
H11C H 0.4929 0.2383 0.1556 0.043 Uiso 1 1 calc R U . . .
H11B H 0.5573 0.2677 0.0440 0.043 Uiso 1 1 calc R U . . .
H11A H 0.3627 0.2612 0.0559 0.043 Uiso 1 1 calc R U . . .
C12A C 0.6578(6) 0.5190(5) 0.1279(4) 0.0232(11) Uani 1 1 d . . . . .
H12A H 0.7491 0.5017 0.0917 0.028 Uiso 1 1 calc R U . . .
C13A C 0.6408(6) 0.6374(5) 0.1794(4) 0.0229(11) Uani 1 1 d . . . . .
H13A H 0.7204 0.7178 0.1859 0.028 Uiso 1 1 calc R U . . .
N14A N 0.4924(5) 0.6243(4) 0.2206(3) 0.0184(8) Uani 1 1 d . . . . .
N1B N 0.2298(6) 1.0190(5) 0.2347(4) 0.0320(11) Uani 1 1 d . . . . .
O11B O 0.1991(5) 0.9776(4) 0.3228(3) 0.0341(9) Uani 1 1 d . . . . .
O12B O 0.3110(5) 0.9548(4) 0.1752(3) 0.0267(8) Uani 1 1 d . . . . .
O13B O 0.1803(7) 1.1159(5) 0.2087(5) 0.0576(14) Uani 1 1 d . . . . .
N1C N 0.0733(5) 0.6939(5) 0.0750(3) 0.0258(10) Uani 1 1 d . . . . .
O11C O 0.0270(4) 0.7416(4) 0.1640(3) 0.0245(8) Uani 1 1 d . . . . .
O12C O 0.2262(4) 0.6815(4) 0.0838(3) 0.0229(7) Uani 1 1 d . . . . .
O13C O -0.0247(5) 0.6608(5) -0.0107(3) 0.0446(12) Uani 1 1 d . . . . .
N1D N 0.4149(5) 0.7741(4) 0.5270(3) 0.0230(9) Uani 1 1 d . . . . .
O11D O 0.3713(4) 0.8751(3) 0.4933(3) 0.0238(8) Uani 1 1 d . . . . .
O12D O 0.4070(4) 0.6758(4) 0.4544(3) 0.0221(7) Uani 1 1 d . . . . .
O13D O 0.4587(5) 0.7738(4) 0.6246(3) 0.0364(10) Uani 1 1 d . . . . .
O1E O 0.5800(4) 0.9108(4) 0.3363(3) 0.0251(8) Uani 1 1 d . . . . .
H2E H 0.6410 0.9403 0.2946 0.030 Uiso 1 1 d R U . . .
H1E H 0.5938 0.9638 0.3839 0.030 Uiso 1 1 d R U . . .
O1F O 0.7900(16) 1.0026(10) 0.2123(8) 0.171(5) Uani 1 1 d D U . . .
H1F H 0.8945 1.0192 0.2357 0.205 Uiso 1 1 calc R U . . .
C1F C 0.7623(18) 1.0046(12) 0.0971(9) 0.147(7) Uani 1 1 d D . . . .
H1F3 H 0.7612 1.0949 0.0850 0.221 Uiso 1 1 calc R U . . .
H1F2 H 0.6533 0.9470 0.0635 0.221 Uiso 1 1 calc R U . . .
H1F1 H 0.8533 0.9732 0.0639 0.221 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Eu1 O1E 2.426(3) . ?
Eu1 O11B 2.476(4) . ?
Eu1 O11C 2.494(3) . ?
Eu1 N14A 2.511(4) . ?
Eu1 O12D 2.519(3) . ?
Eu1 N1A 2.547(4) . ?
Eu1 O12C 2.549(3) . ?
Eu1 N8A 2.555(4) . ?
Eu1 O12B 2.567(4) . ?
Eu1 O11D 2.572(3) . ?
Eu1 N1B 2.936(5) . ?
Eu1 N1C 2.961(4) . ?
N1A C6A 1.341(6) . ?
N1A C2A 1.349(6) . ?
C2A C3A 1.369(7) . ?
C2A H2A 0.9500 . ?
C3A C4A 1.396(8) . ?
C3A H3A 0.9500 . ?
C4A C5A 1.358(7) . ?
C4A H4A 0.9500 . ?
C5A C6A 1.404(6) . ?
C5A H5A 0.9500 . ?
C6A N7A 1.393(6) . ?
N7A N8A 1.366(5) . ?
N7A C71A 1.448(6) . ?
C71A H71C 0.9800 . ?
C71A H71B 0.9800 . ?
C71A H71A 0.9800 . ?
N8A C9A 1.292(6) . ?
C9A C10A 1.448(6) . ?
C9A H9A 0.9500 . ?
C10A N14A 1.333(6) . ?
C10A N11A 1.358(6) . ?
N11A C12A 1.373(7) . ?
N11A C11A 1.461(7) . ?
C11A H11C 0.9800 . ?
C11A H11B 0.9800 . ?
C11A H11A 0.9800 . ?
C12A C13A 1.351(7) . ?
C12A H12A 0.9500 . ?
C13A N14A 1.367(6) . ?
C13A H13A 0.9500 . ?
N1B O13B 1.228(6) . ?
N1B O12B 1.261(6) . ?
N1B O11B 1.275(6) . ?
N1C O13C 1.212(6) . ?
N1C O12C 1.267(5) . ?
N1C O11C 1.283(5) . ?
N1D O13D 1.224(5) . ?
N1D O12D 1.256(5) . ?
N1D O11D 1.283(6) . ?
O1E H2E 0.8178 . ?
O1E H1E 0.7343 . ?
O1F C1F 1.428(5) . ?
O1F H1F 0.8400 . ?
C1F H1F3 0.9800 . ?
C1F H1F2 0.9800 . ?
C1F H1F1 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1E Eu1 O11B 84.30(13) . . ?
O1E Eu1 O11C 140.78(13) . . ?
O11B Eu1 O11C 72.33(13) . . ?
O1E Eu1 N14A 76.25(12) . . ?
O11B Eu1 N14A 154.91(13) . . ?
O11C Eu1 N14A 113.99(12) . . ?
O1E Eu1 O12D 81.89(12) . . ?
O11B Eu1 O12D 117.56(12) . . ?
O11C Eu1 O12D 136.78(11) . . ?
N14A Eu1 O12D 75.57(12) . . ?
O1E Eu1 N1A 138.85(12) . . ?
O11B Eu1 N1A 79.70(13) . . ?
O11C Eu1 N1A 67.96(12) . . ?
N14A Eu1 N1A 125.39(13) . . ?
O12D Eu1 N1A 72.69(12) . . ?
O1E Eu1 O12C 111.46(11) . . ?
O11B Eu1 O12C 107.07(13) . . ?
O11C Eu1 O12C 50.60(11) . . ?
N14A Eu1 O12C 66.83(12) . . ?
O12D Eu1 O12C 134.62(11) . . ?
N1A Eu1 O12C 109.45(12) . . ?
O1E Eu1 N8A 136.50(12) . . ?
O11B Eu1 N8A 137.48(13) . . ?
O11C Eu1 N8A 77.09(12) . . ?
N14A Eu1 N8A 65.94(12) . . ?
O12D Eu1 N8A 68.87(12) . . ?
N1A Eu1 N8A 61.59(12) . . ?
O12C Eu1 N8A 73.09(12) . . ?
O1E Eu1 O12B 71.51(12) . . ?
O11B Eu1 O12B 50.71(12) . . ?
O11C Eu1 O12B 69.30(12) . . ?
N14A Eu1 O12B 107.10(12) . . ?
O12D Eu1 O12B 151.39(12) . . ?
N1A Eu1 O12B 121.87(12) . . ?
O12C Eu1 O12B 67.62(12) . . ?
N8A Eu1 O12B 138.98(12) . . ?
O1E Eu1 O11D 67.42(12) . . ?
O11B Eu1 O11D 68.40(13) . . ?
O11C Eu1 O11D 127.21(11) . . ?
N14A Eu1 O11D 116.66(12) . . ?
O12D Eu1 O11D 50.07(11) . . ?
N1A Eu1 O11D 71.45(12) . . ?
O12C Eu1 O11D 175.30(11) . . ?
N8A Eu1 O11D 111.00(12) . . ?
O12B Eu1 O11D 107.89(11) . . ?
O1E Eu1 N1B 78.49(13) . . ?
O11B Eu1 N1B 25.47(13) . . ?
O11C Eu1 N1B 66.80(13) . . ?
N14A Eu1 N1B 132.08(13) . . ?
O12D Eu1 N1B 139.20(13) . . ?
N1A Eu1 N1B 100.15(13) . . ?
O12C Eu1 N1B 86.04(13) . . ?
N8A Eu1 N1B 143.74(13) . . ?
O12B Eu1 N1B 25.37(12) . . ?
O11D Eu1 N1B 89.27(13) . . ?
O1E Eu1 N1C 129.17(12) . . ?
O11B Eu1 N1C 89.87(14) . . ?
O11C Eu1 N1C 25.40(11) . . ?
N14A Eu1 N1C 90.27(13) . . ?
O12D Eu1 N1C 142.15(12) . . ?
N1A Eu1 N1C 88.65(12) . . ?
O12C Eu1 N1C 25.20(11) . . ?
N8A Eu1 N1C 73.30(13) . . ?
O12B Eu1 N1C 66.20(12) . . ?
O11D Eu1 N1C 152.45(12) . . ?
N1B Eu1 N1C 75.35(14) . . ?
C6A N1A C2A 117.2(4) . . ?
C6A N1A Eu1 122.3(3) . . ?
C2A N1A Eu1 120.5(3) . . ?
N1A C2A C3A 124.2(5) . . ?
N1A C2A H2A 117.9 . . ?
C3A C2A H2A 117.9 . . ?
C2A C3A C4A 117.6(5) . . ?
C2A C3A H3A 121.2 . . ?
C4A C3A H3A 121.2 . . ?
C5A C4A C3A 119.8(5) . . ?
C5A C4A H4A 120.1 . . ?
C3A C4A H4A 120.1 . . ?
C4A C5A C6A 119.0(5) . . ?
C4A C5A H5A 120.5 . . ?
C6A C5A H5A 120.5 . . ?
N1A C6A N7A 117.2(4) . . ?
N1A C6A C5A 122.2(4) . . ?
N7A C6A C5A 120.7(4) . . ?
N8A N7A C6A 115.9(4) . . ?
N8A N7A C71A 120.6(4) . . ?
C6A N7A C71A 123.2(4) . . ?
N7A C71A H71C 109.5 . . ?
N7A C71A H71B 109.5 . . ?
H71C C71A H71B 109.5 . . ?
N7A C71A H71A 109.5 . . ?
H71C C71A H71A 109.5 . . ?
H71B C71A H71A 109.5 . . ?
C9A N8A N7A 120.1(4) . . ?
C9A N8A Eu1 119.0(3) . . ?
N7A N8A Eu1 120.8(3) . . ?
N8A C9A C10A 115.5(4) . . ?
N8A C9A H9A 122.2 . . ?
C10A C9A H9A 122.2 . . ?
N14A C10A N11A 110.9(4) . . ?
N14A C10A C9A 124.2(4) . . ?
N11A C10A C9A 124.8(4) . . ?
C10A N11A C12A 106.6(4) . . ?
C10A N11A C11A 126.6(4) . . ?
C12A N11A C11A 126.8(4) . . ?
N11A C11A H11C 109.5 . . ?
N11A C11A H11B 109.5 . . ?
H11C C11A H11B 109.5 . . ?
N11A C11A H11A 109.5 . . ?
H11C C11A H11A 109.5 . . ?
H11B C11A H11A 109.5 . . ?
C13A C12A N11A 106.8(4) . . ?
C13A C12A H12A 126.6 . . ?
N11A C12A H12A 126.6 . . ?
C12A C13A N14A 110.0(5) . . ?
C12A C13A H13A 125.0 . . ?
N14A C13A H13A 125.0 . . ?
C10A N14A C13A 105.7(4) . . ?
C10A N14A Eu1 114.3(3) . . ?
C13A N14A Eu1 138.4(3) . . ?
O13B N1B O12B 121.8(5) . . ?
O13B N1B O11B 121.3(5) . . ?
O12B N1B O11B 116.9(4) . . ?
O13B N1B Eu1 172.3(4) . . ?
O12B N1B Eu1 60.7(3) . . ?
O11B N1B Eu1 56.7(2) . . ?
N1B O11B Eu1 97.9(3) . . ?
N1B O12B Eu1 93.9(3) . . ?
O13C N1C O12C 122.9(5) . . ?
O13C N1C O11C 121.6(4) . . ?
O12C N1C O11C 115.4(4) . . ?
O13C N1C Eu1 177.4(4) . . ?
O12C N1C Eu1 58.9(2) . . ?
O11C N1C Eu1 56.5(2) . . ?
N1C O11C Eu1 98.1(3) . . ?
N1C O12C Eu1 95.9(3) . . ?
O13D N1D O12D 122.4(5) . . ?
O13D N1D O11D 121.4(4) . . ?
O12D N1D O11D 116.2(4) . . ?
O13D N1D Eu1 178.5(3) . . ?
O12D N1D Eu1 56.8(2) . . ?
O11D N1D Eu1 59.4(2) . . ?
N1D O11D Eu1 95.2(3) . . ?
N1D O12D Eu1 98.5(3) . . ?
Eu1 O1E H2E 128.0 . . ?
Eu1 O1E H1E 117.0 . . ?
H2E O1E H1E 104.9 . . ?
C1F O1F H1F 109.5 . . ?
O1F C1F H1F3 109.5 . . ?
O1F C1F H1F2 109.5 . . ?
H1F3 C1F H1F2 109.5 . . ?
O1F C1F H1F1 109.5 . . ?
H1F3 C1F H1F1 109.5 . . ?
H1F2 C1F H1F1 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6A N1A C2A C3A 0.9(7) . . . . ?
Eu1 N1A C2A C3A 177.6(4) . . . . ?
N1A C2A C3A C4A 1.6(8) . . . . ?
C2A C3A C4A C5A -2.1(7) . . . . ?
C3A C4A C5A C6A 0.1(7) . . . . ?
C2A N1A C6A N7A 178.4(4) . . . . ?
Eu1 N1A C6A N7A 1.8(5) . . . . ?
C2A N1A C6A C5A -3.0(6) . . . . ?
Eu1 N1A C6A C5A -179.6(3) . . . . ?
C4A C5A C6A N1A 2.5(7) . . . . ?
C4A C5A C6A N7A -178.9(4) . . . . ?
N1A C6A N7A N8A 10.3(6) . . . . ?
C5A C6A N7A N8A -168.3(4) . . . . ?
N1A C6A N7A C71A -175.6(4) . . . . ?
C5A C6A N7A C71A 5.8(7) . . . . ?
C6A N7A N8A C9A 166.3(4) . . . . ?
C71A N7A N8A C9A -8.0(6) . . . . ?
C6A N7A N8A Eu1 -17.8(5) . . . . ?
C71A N7A N8A Eu1 167.9(3) . . . . ?
N7A N8A C9A C10A -179.9(4) . . . . ?
Eu1 N8A C9A C10A 4.1(5) . . . . ?
N8A C9A C10A N14A 5.0(7) . . . . ?
N8A C9A C10A N11A -173.2(4) . . . . ?
N14A C10A N11A C12A 0.3(5) . . . . ?
C9A C10A N11A C12A 178.6(4) . . . . ?
N14A C10A N11A C11A -179.3(5) . . . . ?
C9A C10A N11A C11A -0.9(8) . . . . ?
C10A N11A C12A C13A 0.3(5) . . . . ?
C11A N11A C12A C13A 179.8(5) . . . . ?
N11A C12A C13A N14A -0.7(6) . . . . ?
N11A C10A N14A C13A -0.7(5) . . . . ?
C9A C10A N14A C13A -179.1(5) . . . . ?
N11A C10A N14A Eu1 167.4(3) . . . . ?
C9A C10A N14A Eu1 -11.0(6) . . . . ?
C12A C13A N14A C10A 0.8(6) . . . . ?
C12A C13A N14A Eu1 -162.6(4) . . . . ?
O13B N1B O11B Eu1 171.2(5) . . . . ?
O12B N1B O11B Eu1 -7.8(5) . . . . ?
O13B N1B O12B Eu1 -171.6(5) . . . . ?
O11B N1B O12B Eu1 7.4(5) . . . . ?
O13C N1C O11C Eu1 177.8(5) . . . . ?
O12C N1C O11C Eu1 -0.7(5) . . . . ?
O13C N1C O12C Eu1 -177.8(5) . . . . ?
O11C N1C O12C Eu1 0.6(4) . . . . ?
O13D N1D O11D Eu1 -178.5(4) . . . . ?
O12D N1D O11D Eu1 0.4(4) . . . . ?
O13D N1D O12D Eu1 178.4(4) . . . . ?
O11D N1D O12D Eu1 -0.4(4) . . . . ?

_refine_diff_density_max         2.474
_refine_diff_density_min         -1.892
_refine_diff_density_rms         0.146

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_14
_database_code_depnum_ccdc_archive 'CCDC 1435581'
_audit_update_record             
;
2015-11-06 deposited with the CCDC.	2024-07-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H17 N8 Nd O10, C2 H3 N'
_chemical_formula_sum            'C14 H20 N9 Nd O10'
_chemical_formula_weight         618.63

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Nd Nd -0.1943 3.0179 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.3168(5)
_cell_length_b                   11.3880(6)
_cell_length_c                   13.4939(8)
_cell_angle_alpha                110.119(5)
_cell_angle_beta                 107.600(5)
_cell_angle_gamma                92.758(5)
_cell_volume                     1127.23(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    4331
_cell_measurement_theta_min      3.3406
_cell_measurement_theta_max      26.4476

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.823
_exptl_crystal_F_000             614
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.08
_exptl_absorpt_coefficient_mu    2.373
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.55231
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21t (release 14-08-2012 CrysAlis171 .NET)
(compiled Aug 14 2012,18:12:40)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?

_diffrn_ambient_temperature      295(2)
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Eos
_diffrn_detector_area_resol_mean 16.1544
_diffrn_measurement_method       ω-scan

_diffrn_reflns_number            7629
_diffrn_reflns_av_unetI/netI     0.0199
_diffrn_reflns_av_R_equivalents  0.0119
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.347
_diffrn_reflns_theta_max         26.505
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.910
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.910
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.910
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             4261
_reflns_number_gt                4103
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlis Pro (Agilent Technologies (2011))'
_computing_cell_refinement       'CrysAlis Pro (Agilent Technologies (2011))'
_computing_data_reduction        'CrysAlis Pro (Agilent Technologies (2011))'
_computing_structure_solution    'SIR92 (Altomare et al., 1993)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Mercury (MacRae et al., 2009)'
_computing_publication_material  'SHELXL-2013 (Sheldrick, 2013)'


_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0170P)²+0.5393P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4261
_refine_ls_number_parameters     315
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0166
_refine_ls_R_factor_gt           0.0156
_refine_ls_wR_factor_ref         0.0384
_refine_ls_wR_factor_gt          0.0380
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_restrained_S_all      1.083
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Nd1 Nd 0.31148(2) 0.34292(2) 0.74460(2) 0.01353(4) Uani 1 1 d . . . . .
N1A N 0.0338(2) 0.43598(15) 0.68516(15) 0.0183(4) Uani 1 1 d . . . . .
C2A C -0.0269(3) 0.5063(2) 0.76478(19) 0.0227(4) Uani 1 1 d . . . . .
H2A H 0.0386 0.5269 0.8397 0.027 Uiso 1 1 calc R U . . .
C3A C -0.1799(3) 0.5489(2) 0.74092(19) 0.0254(5) Uani 1 1 d . . . . .
H3A H -0.2190 0.5952 0.7980 0.030 Uiso 1 1 calc R U . . .
C4A C -0.2746(3) 0.5208(2) 0.6293(2) 0.0254(5) Uani 1 1 d . . . . .
H4A H -0.3775 0.5505 0.6108 0.030 Uiso 1 1 calc R U . . .
C5A C -0.2177(3) 0.4496(2) 0.54613(19) 0.0218(4) Uani 1 1 d . . . . .
H5A H -0.2800 0.4311 0.4710 0.026 Uiso 1 1 calc R U . . .
C6A C -0.0628(2) 0.40522(18) 0.57713(18) 0.0168(4) Uani 1 1 d . . . . .
N7A N -0.0035(2) 0.32808(16) 0.49595(14) 0.0191(4) Uani 1 1 d . . . . .
C71A C -0.1036(3) 0.2759(2) 0.37655(18) 0.0233(5) Uani 1 1 d . . . . .
H71C H -0.0599 0.3211 0.3392 0.035 Uiso 1 1 calc R U . . .
H71B H -0.2211 0.2844 0.3665 0.035 Uiso 1 1 calc R U . . .
H71A H -0.0956 0.1877 0.3453 0.035 Uiso 1 1 calc R U . . .
N8A N 0.1566(2) 0.30141(15) 0.53264(14) 0.0159(3) Uani 1 1 d . . . . .
C9A C 0.2269(3) 0.24139(18) 0.46066(17) 0.0172(4) Uani 1 1 d . . . . .
H9A H 0.1716 0.2160 0.3837 0.021 Uiso 1 1 calc R U . . .
C10A C 0.3966(3) 0.21615(18) 0.50695(18) 0.0181(4) Uani 1 1 d . . . . .
N11A N 0.4846(2) 0.14525(16) 0.44482(15) 0.0200(4) Uani 1 1 d . . . . .
C11A C 0.4276(3) 0.0822(2) 0.32299(19) 0.0298(5) Uani 1 1 d . . . . .
H11C H 0.3123 0.0379 0.2960 0.045 Uiso 1 1 calc R U . . .
H11B H 0.5013 0.0228 0.3027 0.045 Uiso 1 1 calc R U . . .
H11A H 0.4316 0.1443 0.2901 0.045 Uiso 1 1 calc R U . . .
C12A C 0.6362(3) 0.1411(2) 0.51892(19) 0.0214(4) Uani 1 1 d . . . . .
H12A H 0.7232 0.0995 0.5014 0.026 Uiso 1 1 calc R U . . .
C13A C 0.6348(3) 0.20976(19) 0.62341(19) 0.0219(4) Uani 1 1 d . . . . .
H13A H 0.7227 0.2230 0.6901 0.026 Uiso 1 1 calc R U . . .
N14A N 0.4849(2) 0.25636(16) 0.61586(15) 0.0195(4) Uani 1 1 d . . . . .
N1B N 0.6565(2) 0.32765(18) 0.89377(15) 0.0261(4) Uani 1 1 d . . . . .
O11B O 0.5408(2) 0.23104(14) 0.84101(13) 0.0296(4) Uani 1 1 d . . . . .
O12B O 0.61315(18) 0.43190(14) 0.88723(13) 0.0252(3) Uani 1 1 d . . . . .
O13B O 0.8016(2) 0.32380(18) 0.94766(15) 0.0428(5) Uani 1 1 d . . . . .
N1C N 0.4086(2) 0.62144(16) 0.80450(16) 0.0217(4) Uani 1 1 d . . . . .
O11C O 0.40369(18) 0.53735(13) 0.71169(12) 0.0219(3) Uani 1 1 d . . . . .
O12C O 0.36536(19) 0.58237(13) 0.87149(12) 0.0236(3) Uani 1 1 d . . . . .
O13C O 0.4525(2) 0.73397(14) 0.82665(15) 0.0381(4) Uani 1 1 d . . . . .
N1D N 0.0849(2) 0.09157(16) 0.64961(16) 0.0238(4) Uani 1 1 d . . . . .
O11D O 0.2416(2) 0.09975(14) 0.66165(16) 0.0344(4) Uani 1 1 d . . . . .
O12D O 0.03129(18) 0.19459(13) 0.68405(13) 0.0258(3) Uani 1 1 d . . . . .
O13D O -0.0118(2) -0.01031(16) 0.60645(19) 0.0509(5) Uani 1 1 d . . . . .
O1E O 0.2498(2) 0.36135(16) 0.91518(14) 0.0249(3) Uani 1 1 d . . . . .
H1E H 0.285(3) 0.418(2) 0.965(2) 0.027(8) Uiso 1 1 d . . . . .
C1E C 0.1960(3) 0.2609(3) 0.9454(2) 0.0391(6) Uani 1 1 d . . . . .
H1E3 H 0.1446 0.1859 0.8790 0.059 Uiso 1 1 calc R U . . .
H1E2 H 0.1141 0.2860 0.9825 0.059 Uiso 1 1 calc R U . . .
H1E1 H 0.2934 0.2436 0.9951 0.059 Uiso 1 1 calc R U . . .
N1F N -0.0233(4) -0.1098(3) 0.8442(3) 0.0820(10) Uani 1 1 d . . . . .
C2F C 0.1038(4) -0.0869(3) 0.9131(3) 0.0479(7) Uani 1 1 d . . . . .
C3F C 0.2682(4) -0.0580(3) 1.0007(3) 0.0606(9) Uani 1 1 d . . . . .
H3F3 H 0.3510 -0.0951 0.9686 0.091 Uiso 1 1 calc R U . . .
H3F2 H 0.2592 -0.0920 1.0551 0.091 Uiso 1 1 calc R U . . .
H3F1 H 0.3037 0.0323 1.0364 0.091 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Nd1 O1E 2.4491(16) . ?
Nd1 O11C 2.5311(14) . ?
Nd1 O12D 2.5439(14) . ?
Nd1 O12B 2.5533(15) . ?
Nd1 N14A 2.5580(17) . ?
Nd1 O11D 2.5649(15) . ?
Nd1 O12C 2.6028(15) . ?
Nd1 N1A 2.6076(16) . ?
Nd1 O11B 2.6126(15) . ?
Nd1 N8A 2.6165(17) . ?
Nd1 N1D 2.9805(17) . ?
Nd1 N1C 2.9934(17) . ?
N1A C6A 1.344(3) . ?
N1A C2A 1.351(3) . ?
C2A C3A 1.370(3) . ?
C2A H2A 0.9300 . ?
C3A C4A 1.385(3) . ?
C3A H3A 0.9300 . ?
C4A C5A 1.368(3) . ?
C4A H4A 0.9300 . ?
C5A C6A 1.404(3) . ?
C5A H5A 0.9300 . ?
C6A N7A 1.386(3) . ?
N7A N8A 1.362(2) . ?
N7A C71A 1.458(3) . ?
C71A H71C 0.9600 . ?
C71A H71B 0.9600 . ?
C71A H71A 0.9600 . ?
N8A C9A 1.295(3) . ?
C9A C10A 1.447(3) . ?
C9A H9A 0.9300 . ?
C10A N14A 1.327(3) . ?
C10A N11A 1.361(3) . ?
N11A C12A 1.366(3) . ?
N11A C11A 1.458(3) . ?
C11A H11C 0.9600 . ?
C11A H11B 0.9600 . ?
C11A H11A 0.9600 . ?
C12A C13A 1.361(3) . ?
C12A H12A 0.9300 . ?
C13A N14A 1.367(3) . ?
C13A H13A 0.9300 . ?
N1B O13B 1.218(2) . ?
N1B O11B 1.261(2) . ?
N1B O12B 1.281(2) . ?
N1C O13C 1.221(2) . ?
N1C O12C 1.266(2) . ?
N1C O11C 1.276(2) . ?
N1D O13D 1.222(2) . ?
N1D O11D 1.258(2) . ?
N1D O12D 1.262(2) . ?
O1E C1E 1.434(3) . ?
O1E H1E 0.72(3) . ?
C1E H1E3 0.9600 . ?
C1E H1E2 0.9600 . ?
C1E H1E1 0.9600 . ?
N1F C2F 1.123(4) . ?
C2F C3F 1.445(4) . ?
C3F H3F3 0.9600 . ?
C3F H3F2 0.9600 . ?
C3F H3F1 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1E Nd1 O11C 121.38(5) . . ?
O1E Nd1 O12D 72.88(5) . . ?
O11C Nd1 O12D 135.76(5) . . ?
O1E Nd1 O12B 81.11(5) . . ?
O11C Nd1 O12B 75.78(5) . . ?
O12D Nd1 O12B 146.78(5) . . ?
O1E Nd1 N14A 148.68(5) . . ?
O11C Nd1 N14A 78.00(5) . . ?
O12D Nd1 N14A 111.87(5) . . ?
O12B Nd1 N14A 80.65(5) . . ?
O1E Nd1 O11D 93.81(6) . . ?
O11C Nd1 O11D 144.80(5) . . ?
O12D Nd1 O11D 49.60(5) . . ?
O12B Nd1 O11D 113.83(5) . . ?
N14A Nd1 O11D 70.88(5) . . ?
O1E Nd1 O12C 71.55(5) . . ?
O11C Nd1 O12C 49.85(5) . . ?
O12D Nd1 O12C 123.23(5) . . ?
O12B Nd1 O12C 64.41(5) . . ?
N14A Nd1 O12C 121.57(5) . . ?
O11D Nd1 O12C 165.35(5) . . ?
O1E Nd1 N1A 87.19(5) . . ?
O11C Nd1 N1A 74.29(5) . . ?
O12D Nd1 N1A 64.33(5) . . ?
O12B Nd1 N1A 135.50(5) . . ?
N14A Nd1 N1A 123.35(5) . . ?
O11D Nd1 N1A 109.67(5) . . ?
O12C Nd1 N1A 71.14(5) . . ?
O1E Nd1 O11B 76.56(5) . . ?
O11C Nd1 O11B 120.17(5) . . ?
O12D Nd1 O11B 103.54(5) . . ?
O12B Nd1 O11B 49.28(5) . . ?
N14A Nd1 O11B 72.24(5) . . ?
O11D Nd1 O11B 65.26(5) . . ?
O12C Nd1 O11B 109.31(5) . . ?
N1A Nd1 O11B 162.32(5) . . ?
O1E Nd1 N8A 141.10(5) . . ?
O11C Nd1 N8A 72.54(5) . . ?
O12D Nd1 N8A 73.86(5) . . ?
O12B Nd1 N8A 136.75(5) . . ?
N14A Nd1 N8A 64.63(5) . . ?
O11D Nd1 N8A 79.44(5) . . ?
O12C Nd1 N8A 112.16(5) . . ?
N1A Nd1 N8A 60.28(5) . . ?
O11B Nd1 N8A 131.13(5) . . ?
O1E Nd1 N1D 83.42(6) . . ?
O11C Nd1 N1D 146.96(5) . . ?
O12D Nd1 N1D 24.82(5) . . ?
O12B Nd1 N1D 133.59(5) . . ?
N14A Nd1 N1D 91.03(5) . . ?
O11D Nd1 N1D 24.80(5) . . ?
O12C Nd1 N1D 146.89(5) . . ?
N1A Nd1 N1D 86.68(5) . . ?
O11B Nd1 N1D 84.60(5) . . ?
N8A Nd1 N1D 74.59(5) . . ?
O1E Nd1 N1C 96.46(5) . . ?
O11C Nd1 N1C 24.95(5) . . ?
O12D Nd1 N1C 134.62(5) . . ?
O12B Nd1 N1C 67.63(5) . . ?
N14A Nd1 N1C 99.82(5) . . ?
O11D Nd1 N1C 169.73(6) . . ?
O12C Nd1 N1C 24.91(5) . . ?
N1A Nd1 N1C 71.32(5) . . ?
O11B Nd1 N1C 116.91(5) . . ?
N8A Nd1 N1C 92.72(5) . . ?
N1D Nd1 N1C 157.96(5) . . ?
C6A N1A C2A 117.86(17) . . ?
C6A N1A Nd1 122.40(13) . . ?
C2A N1A Nd1 119.31(14) . . ?
N1A C2A C3A 123.4(2) . . ?
N1A C2A H2A 118.3 . . ?
C3A C2A H2A 118.3 . . ?
C2A C3A C4A 118.0(2) . . ?
C2A C3A H3A 121.0 . . ?
C4A C3A H3A 121.0 . . ?
C5A C4A C3A 120.4(2) . . ?
C5A C4A H4A 119.8 . . ?
C3A C4A H4A 119.8 . . ?
C4A C5A C6A 118.3(2) . . ?
C4A C5A H5A 120.9 . . ?
C6A C5A H5A 120.9 . . ?
N1A C6A N7A 117.52(17) . . ?
N1A C6A C5A 121.98(19) . . ?
N7A C6A C5A 120.50(19) . . ?
N8A N7A C6A 116.68(16) . . ?
N8A N7A C71A 120.02(16) . . ?
C6A N7A C71A 123.30(16) . . ?
N7A C71A H71C 109.5 . . ?
N7A C71A H71B 109.5 . . ?
H71C C71A H71B 109.5 . . ?
N7A C71A H71A 109.5 . . ?
H71C C71A H71A 109.5 . . ?
H71B C71A H71A 109.5 . . ?
C9A N8A N7A 119.79(17) . . ?
C9A N8A Nd1 118.49(13) . . ?
N7A N8A Nd1 121.27(12) . . ?
N8A C9A C10A 116.08(18) . . ?
N8A C9A H9A 122.0 . . ?
C10A C9A H9A 122.0 . . ?
N14A C10A N11A 111.11(17) . . ?
N14A C10A C9A 124.34(18) . . ?
N11A C10A C9A 124.52(19) . . ?
C10A N11A C12A 106.73(18) . . ?
C10A N11A C11A 127.12(18) . . ?
C12A N11A C11A 126.13(18) . . ?
N11A C11A H11C 109.5 . . ?
N11A C11A H11B 109.5 . . ?
H11C C11A H11B 109.5 . . ?
N11A C11A H11A 109.5 . . ?
H11C C11A H11A 109.5 . . ?
H11B C11A H11A 109.5 . . ?
C13A C12A N11A 106.59(18) . . ?
C13A C12A H12A 126.7 . . ?
N11A C12A H12A 126.7 . . ?
C12A C13A N14A 109.92(19) . . ?
C12A C13A H13A 125.0 . . ?
N14A C13A H13A 125.0 . . ?
C10A N14A C13A 105.65(17) . . ?
C10A N14A Nd1 114.82(12) . . ?
C13A N14A Nd1 137.23(14) . . ?
O13B N1B O11B 122.9(2) . . ?
O13B N1B O12B 121.2(2) . . ?
O11B N1B O12B 115.92(17) . . ?
N1B O11B Nd1 96.09(11) . . ?
N1B O12B Nd1 98.37(12) . . ?
O13C N1C O12C 122.12(19) . . ?
O13C N1C O11C 121.10(19) . . ?
O12C N1C O11C 116.79(16) . . ?
O13C N1C Nd1 177.49(15) . . ?
O12C N1C Nd1 60.01(9) . . ?
O11C N1C Nd1 56.80(9) . . ?
N1C O11C Nd1 98.25(11) . . ?
N1C O12C Nd1 95.08(11) . . ?
O13D N1D O11D 122.29(18) . . ?
O13D N1D O12D 121.17(19) . . ?
O11D N1D O12D 116.54(16) . . ?
O13D N1D Nd1 177.08(16) . . ?
O11D N1D Nd1 58.77(10) . . ?
O12D N1D Nd1 57.83(9) . . ?
N1D O11D Nd1 96.42(11) . . ?
N1D O12D Nd1 97.35(11) . . ?
C1E O1E Nd1 127.87(15) . . ?
C1E O1E H1E 108(2) . . ?
Nd1 O1E H1E 121(2) . . ?
O1E C1E H1E3 109.5 . . ?
O1E C1E H1E2 109.5 . . ?
H1E3 C1E H1E2 109.5 . . ?
O1E C1E H1E1 109.5 . . ?
H1E3 C1E H1E1 109.5 . . ?
H1E2 C1E H1E1 109.5 . . ?
N1F C2F C3F 179.3(4) . . ?
C2F C3F H3F3 109.5 . . ?
C2F C3F H3F2 109.5 . . ?
H3F3 C3F H3F2 109.5 . . ?
C2F C3F H3F1 109.5 . . ?
H3F3 C3F H3F1 109.5 . . ?
H3F2 C3F H3F1 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6A N1A C2A C3A -0.9(3) . . . . ?
Nd1 N1A C2A C3A -173.60(16) . . . . ?
N1A C2A C3A C4A -1.7(3) . . . . ?
C2A C3A C4A C5A 1.7(3) . . . . ?
C3A C4A C5A C6A 0.7(3) . . . . ?
C2A N1A C6A N7A -177.03(17) . . . . ?
Nd1 N1A C6A N7A -4.6(2) . . . . ?
C2A N1A C6A C5A 3.5(3) . . . . ?
Nd1 N1A C6A C5A 175.96(14) . . . . ?
C4A C5A C6A N1A -3.4(3) . . . . ?
C4A C5A C6A N7A 177.13(18) . . . . ?
N1A C6A N7A N8A -6.9(2) . . . . ?
C5A C6A N7A N8A 172.58(17) . . . . ?
N1A C6A N7A C71A 172.92(18) . . . . ?
C5A C6A N7A C71A -7.6(3) . . . . ?
C6A N7A N8A C9A -172.64(17) . . . . ?
C71A N7A N8A C9A 7.5(3) . . . . ?
C6A N7A N8A Nd1 15.2(2) . . . . ?
C71A N7A N8A Nd1 -164.58(13) . . . . ?
N7A N8A C9A C10A -179.51(16) . . . . ?
Nd1 N8A C9A C10A -7.2(2) . . . . ?
N8A C9A C10A N14A -3.9(3) . . . . ?
N8A C9A C10A N11A 174.19(17) . . . . ?
N14A C10A N11A C12A -0.1(2) . . . . ?
C9A C10A N11A C12A -178.41(18) . . . . ?
N14A C10A N11A C11A 178.21(19) . . . . ?
C9A C10A N11A C11A -0.1(3) . . . . ?
C10A N11A C12A C13A -0.1(2) . . . . ?
C11A N11A C12A C13A -178.37(19) . . . . ?
N11A C12A C13A N14A 0.2(2) . . . . ?
N11A C10A N14A C13A 0.2(2) . . . . ?
C9A C10A N14A C13A 178.52(18) . . . . ?
N11A C10A N14A Nd1 -165.61(12) . . . . ?
C9A C10A N14A Nd1 12.7(2) . . . . ?
C12A C13A N14A C10A -0.2(2) . . . . ?
C12A C13A N14A Nd1 160.62(15) . . . . ?
O13B N1B O11B Nd1 -173.95(19) . . . . ?
O12B N1B O11B Nd1 5.71(18) . . . . ?
O13B N1B O12B Nd1 173.80(18) . . . . ?
O11B N1B O12B Nd1 -5.87(19) . . . . ?
O13C N1C O11C Nd1 178.37(16) . . . . ?
O12C N1C O11C Nd1 -1.85(17) . . . . ?
O13C N1C O12C Nd1 -178.43(17) . . . . ?
O11C N1C O12C Nd1 1.78(17) . . . . ?
O13D N1D O11D Nd1 176.8(2) . . . . ?
O12D N1D O11D Nd1 -2.86(19) . . . . ?
O13D N1D O12D Nd1 -176.77(19) . . . . ?
O11D N1D O12D Nd1 2.9(2) . . . . ?

_refine_diff_density_max         0.468
_refine_diff_density_min         -0.446
_refine_diff_density_rms         0.062

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_03
_database_code_depnum_ccdc_archive 'CCDC 1052299'
_audit_update_record             
;
2016-01-10 deposited with the CCDC.	2024-07-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C25 H26 F9 N10 Nd O9 S3'
_chemical_formula_sum            'C25 H26 F9 N10 Nd O9 S3'
_chemical_formula_weight         1021.98

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Nd Nd -0.1943 3.0179 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x+1/2, y, z+1/2'
'x+1/2, -y, z'

_cell_length_a                   10.7762(2)
_cell_length_b                   17.0625(2)
_cell_length_c                   19.6569(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3614.29(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(1)
_cell_measurement_reflns_used    15903
_cell_measurement_theta_min      3.3160
_cell_measurement_theta_max      28.3100

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.878
_exptl_crystal_F_000             2028
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_exptl_absorpt_coefficient_mu    1.721
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.75216
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(1)
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Eos
_diffrn_detector_area_resol_mean 16.1544
_diffrn_measurement_method       ω-scan
_diffrn_reflns_number            25948
_diffrn_reflns_av_unetI/netI     0.0177
_diffrn_reflns_av_R_equivalents  0.0214
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         3.049
_diffrn_reflns_theta_max         28.329
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.914
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.914
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.742
_diffrn_reflns_point_group_measured_fraction_full 0.864
_reflns_number_total             6680
_reflns_number_gt                6553
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.577
_reflns_Friedel_fraction_max     0.560
_reflns_Friedel_fraction_full    0.720

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlis Pro (Agilent Technologies (2011))'
_computing_cell_refinement       'CrysAlis Pro (Agilent Technologies (2011))'
_computing_data_reduction        'CrysAlis Pro (Agilent Technologies (2011))'
_computing_structure_solution    'SIR92 (Altomare et al., 1993)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Mercury (MacRae et al., 2009)'
_computing_publication_material  'SHELXL-2013 (Sheldrick, 2013)'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0233P)²+5.2900P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 2354 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.182(5)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         6680
_refine_ls_number_parameters     518
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0222
_refine_ls_R_factor_gt           0.0214
_refine_ls_wR_factor_ref         0.0524
_refine_ls_wR_factor_gt          0.0518
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      1.059
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Nd1 Nd 0.44156(2) 0.24243(2) 0.09983(2) 0.00793(5) Uani 1 1 d . . . . .
N1A N 0.4723(3) 0.11829(19) 0.02748(19) 0.0115(7) Uani 1 1 d . . . . .
C2A C 0.4109(4) 0.0506(2) 0.0362(2) 0.0126(8) Uani 1 1 d . . . . .
C3A C 0.4376(4) -0.0164(2) -0.0025(2) 0.0176(9) Uani 1 1 d . . . . .
H3A H 0.3950 -0.0643 0.0054 0.021 Uiso 1 1 calc R U . . .
C4A C 0.5272(4) -0.0107(3) -0.0522(2) 0.0208(10) Uani 1 1 d . . . . .
H4A H 0.5465 -0.0551 -0.0794 0.025 Uiso 1 1 calc R U . . .
C5A C 0.5891(4) 0.0588(3) -0.0627(2) 0.0193(9) Uani 1 1 d . . . . .
H5A H 0.6505 0.0632 -0.0971 0.023 Uiso 1 1 calc R U . . .
C6A C 0.5597(4) 0.1222(3) -0.0217(2) 0.0165(9) Uani 1 1 d . . . . .
H6A H 0.6026 0.1702 -0.0285 0.020 Uiso 1 1 calc R U . . .
N7A N 0.3180(3) 0.04992(18) 0.08462(17) 0.0126(8) Uani 1 1 d . . . . .
C7A C 0.2403(4) -0.0177(2) 0.0996(3) 0.0224(8) Uani 1 1 d . . . . .
H7A1 H 0.2558 -0.0352 0.1463 0.034 Uiso 1 1 calc R U . . .
H7A2 H 0.2601 -0.0603 0.0679 0.034 Uiso 1 1 calc R U . . .
H7A3 H 0.1528 -0.0032 0.0947 0.034 Uiso 1 1 calc R U . . .
N8A N 0.3037(3) 0.11640(19) 0.12214(18) 0.0109(7) Uani 1 1 d . . . . .
C9A C 0.2233(4) 0.1179(2) 0.1707(2) 0.0126(8) Uani 1 1 d . . . . .
H9A H 0.1727 0.0740 0.1812 0.015 Uiso 1 1 calc R U . . .
C10A C 0.2147(4) 0.1904(3) 0.2081(2) 0.0117(9) Uani 1 1 d . . . . .
N11A N 0.1488(3) 0.2008(2) 0.2660(2) 0.0146(8) Uani 1 1 d . . . . .
C11A C 0.0764(5) 0.1424(3) 0.3030(3) 0.0263(11) Uani 1 1 d . . . . .
H11A H 0.0373 0.1064 0.2705 0.039 Uiso 1 1 calc R U . . .
H11B H 0.0121 0.1687 0.3299 0.039 Uiso 1 1 calc R U . . .
H11C H 0.1312 0.1127 0.3333 0.039 Uiso 1 1 calc R U . . .
C12A C 0.1705(4) 0.2755(3) 0.2881(2) 0.0208(10) Uani 1 1 d . . . . .
H12A H 0.1372 0.2998 0.3276 0.025 Uiso 1 1 calc R U . . .
C13A C 0.2495(4) 0.3082(2) 0.2421(2) 0.0191(9) Uani 1 1 d . . . . .
H13A H 0.2804 0.3603 0.2441 0.023 Uiso 1 1 calc R U . . .
N14A N 0.2779(4) 0.2544(2) 0.1920(2) 0.0132(9) Uani 1 1 d . . . . .
N1B N 0.5058(3) 0.3642(2) 0.16768(19) 0.0151(7) Uani 1 1 d . . . . .
C2B C 0.4484(4) 0.4341(2) 0.1649(2) 0.0152(9) Uani 1 1 d . . . . .
C3B C 0.4838(5) 0.4962(3) 0.2077(3) 0.0269(11) Uani 1 1 d . . . . .
H3B H 0.4424 0.5453 0.2054 0.032 Uiso 1 1 calc R U . . .
C4B C 0.5786(5) 0.4849(3) 0.2527(3) 0.0309(12) Uani 1 1 d . . . . .
H4B H 0.6031 0.5260 0.2823 0.037 Uiso 1 1 calc R U . . .
C5B C 0.6387(5) 0.4137(3) 0.2550(3) 0.0287(11) Uani 1 1 d . . . . .
H5B H 0.7058 0.4052 0.2855 0.034 Uiso 1 1 calc R U . . .
C6B C 0.5995(4) 0.3553(3) 0.2123(2) 0.0187(9) Uani 1 1 d . . . . .
H6B H 0.6405 0.3061 0.2142 0.022 Uiso 1 1 calc R U . . .
N7B N 0.3496(3) 0.44125(19) 0.12098(18) 0.0166(8) Uani 1 1 d . . . . .
C7B C 0.2988(5) 0.5163(2) 0.0999(4) 0.0288(10) Uani 1 1 d . . . . .
H7B1 H 0.3084 0.5222 0.0506 0.043 Uiso 1 1 calc R U . . .
H7B2 H 0.3432 0.5587 0.1231 0.043 Uiso 1 1 calc R U . . .
H7B3 H 0.2106 0.5186 0.1118 0.043 Uiso 1 1 calc R U . . .
N8B N 0.3166(3) 0.37545(18) 0.08648(18) 0.0117(8) Uani 1 1 d . . . . .
C9B C 0.2262(4) 0.3787(2) 0.0434(2) 0.0146(9) Uani 1 1 d . . . . .
H9B H 0.1798 0.4253 0.0362 0.018 Uiso 1 1 calc R U . . .
C10B C 0.2003(4) 0.3076(2) 0.0072(2) 0.0133(8) Uani 1 1 d . . . . .
N11B N 0.1157(3) 0.3004(2) -0.0442(2) 0.0176(8) Uani 1 1 d . . . . .
C11B C 0.0329(5) 0.3616(3) -0.0705(3) 0.0291(11) Uani 1 1 d . . . . .
H11D H -0.0220 0.3390 -0.1051 0.044 Uiso 1 1 calc R U . . .
H11E H 0.0825 0.4036 -0.0909 0.044 Uiso 1 1 calc R U . . .
H11F H -0.0170 0.3829 -0.0332 0.044 Uiso 1 1 calc R U . . .
C12B C 0.1253(5) 0.2264(3) -0.0681(3) 0.0216(11) Uani 1 1 d . . . . .
H12B H 0.0790 0.2042 -0.1045 0.026 Uiso 1 1 calc R U . . .
C13B C 0.2136(5) 0.1896(3) -0.0304(3) 0.0192(10) Uani 1 1 d . . . . .
H13B H 0.2388 0.1366 -0.0358 0.023 Uiso 1 1 calc R U . . .
N14B N 0.2603(4) 0.2409(2) 0.0164(2) 0.0141(10) Uani 1 1 d . . . . .
S1C S 0.78991(9) 0.24777(6) 0.06602(6) 0.0142(2) Uani 1 1 d . . . . .
O11C O 0.8032(3) 0.32920(18) 0.0530(2) 0.0296(8) Uani 1 1 d . . . . .
O12C O 0.8281(3) 0.19523(19) 0.01300(18) 0.0242(7) Uani 1 1 d . . . . .
O13C O 0.6724(2) 0.22561(16) 0.0982(3) 0.0201(6) Uani 1 1 d . . . . .
C1C C 0.9033(4) 0.2309(3) 0.1342(3) 0.0246(11) Uani 1 1 d . . . . .
F11C F 0.9156(3) 0.15592(19) 0.14879(18) 0.0387(8) Uani 1 1 d . . . . .
F12C F 0.8723(3) 0.2688(2) 0.19054(17) 0.0429(9) Uani 1 1 d . . . . .
F13C F 1.0134(2) 0.25755(19) 0.11428(18) 0.0387(10) Uani 1 1 d . . . . .
S1D S 0.51042(10) 0.10481(6) 0.24689(6) 0.0145(2) Uani 1 1 d . . . . .
O11D O 0.4147(3) 0.1108(2) 0.29688(17) 0.0227(7) Uani 1 1 d . . . . .
O12D O 0.5229(3) 0.0305(2) 0.2133(2) 0.0300(8) Uani 1 1 d . . . . .
O13D O 0.5185(3) 0.17128(18) 0.20086(17) 0.0177(6) Uani 1 1 d . . . . .
C1D C 0.6521(5) 0.1153(4) 0.2956(3) 0.0333(13) Uani 1 1 d . . . . .
F11D F 0.6639(3) 0.0541(3) 0.3377(2) 0.0741(15) Uani 1 1 d . . . . .
F12D F 0.6524(3) 0.1790(3) 0.3313(2) 0.0674(13) Uani 1 1 d . . . . .
F13D F 0.7523(3) 0.1165(2) 0.25682(17) 0.0388(8) Uani 1 1 d . . . . .
S1E S 0.50499(9) 0.38754(6) -0.03873(6) 0.0136(2) Uani 1 1 d . . . . .
O11E O 0.5340(4) 0.4558(2) 0.00062(19) 0.0295(8) Uani 1 1 d . . . . .
O12E O 0.3963(3) 0.39141(19) -0.08079(17) 0.0219(7) Uani 1 1 d . . . . .
O13E O 0.5188(3) 0.31422(17) -0.00157(16) 0.0177(7) Uani 1 1 d . . . . .
C1E C 0.6285(4) 0.3830(3) -0.1019(3) 0.0270(11) Uani 1 1 d . . . . .
F11E F 0.6208(4) 0.3182(3) -0.1381(2) 0.0663(13) Uani 1 1 d . . . . .
F12E F 0.7387(3) 0.3857(3) -0.07612(19) 0.0681(14) Uani 1 1 d . . . . .
F13E F 0.6171(3) 0.4423(2) -0.14489(18) 0.0506(10) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Nd1 O13D 2.471(3) . ?
Nd1 O13E 2.483(3) . ?
Nd1 O13C 2.504(2) . ?
Nd1 N14A 2.537(5) . ?
Nd1 N14B 2.551(5) . ?
Nd1 N1B 2.565(4) . ?
Nd1 N1A 2.573(3) . ?
Nd1 N8A 2.650(3) . ?
Nd1 N8B 2.652(3) . ?
N1A C2A 1.342(5) . ?
N1A C6A 1.352(6) . ?
C2A N7A 1.382(5) . ?
C2A C3A 1.401(6) . ?
C3A C4A 1.378(6) . ?
C3A H3A 0.9500 . ?
C4A C5A 1.376(7) . ?
C4A H4A 0.9500 . ?
C5A C6A 1.385(6) . ?
C5A H5A 0.9500 . ?
C6A H6A 0.9500 . ?
N7A N8A 1.362(5) . ?
N7A C7A 1.456(5) . ?
C7A H7A1 0.9800 . ?
C7A H7A2 0.9800 . ?
C7A H7A3 0.9800 . ?
N8A C9A 1.289(5) . ?
C9A C10A 1.442(6) . ?
C9A H9A 0.9500 . ?
C10A N14A 1.324(6) . ?
C10A N11A 1.354(6) . ?
N11A C12A 1.366(6) . ?
N11A C11A 1.459(6) . ?
C11A H11A 0.9800 . ?
C11A H11B 0.9800 . ?
C11A H11C 0.9800 . ?
C12A C13A 1.361(6) . ?
C12A H12A 0.9500 . ?
C13A N14A 1.380(6) . ?
C13A H13A 0.9500 . ?
N1B C2B 1.344(6) . ?
N1B C6B 1.345(6) . ?
C2B N7B 1.377(6) . ?
C2B C3B 1.405(6) . ?
C3B C4B 1.364(7) . ?
C3B H3B 0.9500 . ?
C4B C5B 1.378(8) . ?
C4B H4B 0.9500 . ?
C5B C6B 1.369(7) . ?
C5B H5B 0.9500 . ?
C6B H6B 0.9500 . ?
N7B N8B 1.359(5) . ?
N7B C7B 1.452(5) . ?
C7B H7B1 0.9800 . ?
C7B H7B2 0.9800 . ?
C7B H7B3 0.9800 . ?
N8B C9B 1.291(5) . ?
C9B C10B 1.435(6) . ?
C9B H9B 0.9500 . ?
C10B N14B 1.321(6) . ?
C10B N11B 1.366(5) . ?
N11B C12B 1.352(6) . ?
N11B C11B 1.467(5) . ?
C11B H11D 0.9800 . ?
C11B H11E 0.9800 . ?
C11B H11F 0.9800 . ?
C12B C13B 1.360(7) . ?
C12B H12B 0.9500 . ?
C13B N14B 1.366(7) . ?
C13B H13B 0.9500 . ?
S1C O11C 1.420(3) . ?
S1C O12C 1.435(3) . ?
S1C O13C 1.465(3) . ?
S1C C1C 1.836(5) . ?
C1C F11C 1.318(6) . ?
C1C F12C 1.326(6) . ?
C1C F13C 1.330(5) . ?
S1D O11D 1.428(3) . ?
S1D O12D 1.436(4) . ?
S1D O13D 1.454(3) . ?
S1D C1D 1.811(5) . ?
C1D F12D 1.293(7) . ?
C1D F13D 1.322(6) . ?
C1D F11D 1.338(7) . ?
S1E O11E 1.433(4) . ?
S1E O12E 1.435(3) . ?
S1E O13E 1.456(3) . ?
S1E C1E 1.822(5) . ?
C1E F12E 1.292(6) . ?
C1E F11E 1.317(7) . ?
C1E F13E 1.324(6) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O13D Nd1 O13E 140.79(9) . . ?
O13D Nd1 O13C 67.71(12) . . ?
O13E Nd1 O13C 73.32(12) . . ?
O13D Nd1 N14A 72.47(13) . . ?
O13E Nd1 N14A 140.07(11) . . ?
O13C Nd1 N14A 135.16(16) . . ?
O13D Nd1 N14B 140.25(12) . . ?
O13E Nd1 N14B 75.27(12) . . ?
O13C Nd1 N14B 138.69(15) . . ?
N14A Nd1 N14B 85.86(13) . . ?
O13D Nd1 N1B 83.66(11) . . ?
O13E Nd1 N1B 85.82(11) . . ?
O13C Nd1 N1B 80.30(12) . . ?
N14A Nd1 N1B 75.58(12) . . ?
N14B Nd1 N1B 123.33(12) . . ?
O13D Nd1 N1A 89.80(11) . . ?
O13E Nd1 N1A 85.37(11) . . ?
O13C Nd1 N1A 76.74(11) . . ?
N14A Nd1 N1A 123.40(12) . . ?
N14B Nd1 N1A 74.61(12) . . ?
N1B Nd1 N1A 156.92(11) . . ?
O13D Nd1 N8A 69.91(10) . . ?
O13E Nd1 N8A 136.14(11) . . ?
O13C Nd1 N8A 117.78(10) . . ?
N14A Nd1 N8A 63.73(11) . . ?
N14B Nd1 N8A 70.66(11) . . ?
N1B Nd1 N8A 136.28(11) . . ?
N1A Nd1 N8A 59.70(11) . . ?
O13D Nd1 N8B 132.10(11) . . ?
O13E Nd1 N8B 70.66(10) . . ?
O13C Nd1 N8B 126.96(9) . . ?
N14A Nd1 N8B 69.44(12) . . ?
N14B Nd1 N8B 63.65(12) . . ?
N1B Nd1 N8B 59.68(11) . . ?
N1A Nd1 N8B 135.66(11) . . ?
N8A Nd1 N8B 115.21(9) . . ?
C2A N1A C6A 118.5(4) . . ?
C2A N1A Nd1 125.1(3) . . ?
C6A N1A Nd1 116.4(3) . . ?
N1A C2A N7A 116.8(4) . . ?
N1A C2A C3A 122.1(4) . . ?
N7A C2A C3A 121.1(4) . . ?
C4A C3A C2A 118.1(4) . . ?
C4A C3A H3A 120.9 . . ?
C2A C3A H3A 120.9 . . ?
C5A C4A C3A 120.4(4) . . ?
C5A C4A H4A 119.8 . . ?
C3A C4A H4A 119.8 . . ?
C4A C5A C6A 118.4(4) . . ?
C4A C5A H5A 120.8 . . ?
C6A C5A H5A 120.8 . . ?
N1A C6A C5A 122.4(4) . . ?
N1A C6A H6A 118.8 . . ?
C5A C6A H6A 118.8 . . ?
N8A N7A C2A 116.7(3) . . ?
N8A N7A C7A 119.0(3) . . ?
C2A N7A C7A 124.2(3) . . ?
N7A C7A H7A1 109.5 . . ?
N7A C7A H7A2 109.5 . . ?
H7A1 C7A H7A2 109.5 . . ?
N7A C7A H7A3 109.5 . . ?
H7A1 C7A H7A3 109.5 . . ?
H7A2 C7A H7A3 109.5 . . ?
C9A N8A N7A 119.6(3) . . ?
C9A N8A Nd1 118.9(3) . . ?
N7A N8A Nd1 121.5(2) . . ?
N8A C9A C10A 116.0(4) . . ?
N8A C9A H9A 122.0 . . ?
C10A C9A H9A 122.0 . . ?
N14A C10A N11A 111.3(4) . . ?
N14A C10A C9A 123.5(4) . . ?
N11A C10A C9A 125.1(4) . . ?
C10A N11A C12A 107.4(4) . . ?
C10A N11A C11A 127.6(4) . . ?
C12A N11A C11A 124.8(4) . . ?
N11A C11A H11A 109.5 . . ?
N11A C11A H11B 109.5 . . ?
H11A C11A H11B 109.5 . . ?
N11A C11A H11C 109.5 . . ?
H11A C11A H11C 109.5 . . ?
H11B C11A H11C 109.5 . . ?
C13A C12A N11A 106.2(4) . . ?
C13A C12A H12A 126.9 . . ?
N11A C12A H12A 126.9 . . ?
C12A C13A N14A 109.9(4) . . ?
C12A C13A H13A 125.1 . . ?
N14A C13A H13A 125.1 . . ?
C10A N14A C13A 105.3(4) . . ?
C10A N14A Nd1 117.5(3) . . ?
C13A N14A Nd1 135.8(3) . . ?
C2B N1B C6B 118.1(4) . . ?
C2B N1B Nd1 125.0(3) . . ?
C6B N1B Nd1 116.7(3) . . ?
N1B C2B N7B 117.3(4) . . ?
N1B C2B C3B 121.3(4) . . ?
N7B C2B C3B 121.3(4) . . ?
C4B C3B C2B 118.9(5) . . ?
C4B C3B H3B 120.5 . . ?
C2B C3B H3B 120.5 . . ?
C3B C4B C5B 119.9(5) . . ?
C3B C4B H4B 120.0 . . ?
C5B C4B H4B 120.0 . . ?
C6B C5B C4B 118.4(5) . . ?
C6B C5B H5B 120.8 . . ?
C4B C5B H5B 120.8 . . ?
N1B C6B C5B 123.3(4) . . ?
N1B C6B H6B 118.3 . . ?
C5B C6B H6B 118.3 . . ?
N8B N7B C2B 116.3(3) . . ?
N8B N7B C7B 119.1(4) . . ?
C2B N7B C7B 123.3(4) . . ?
N7B C7B H7B1 109.5 . . ?
N7B C7B H7B2 109.5 . . ?
H7B1 C7B H7B2 109.5 . . ?
N7B C7B H7B3 109.5 . . ?
H7B1 C7B H7B3 109.5 . . ?
H7B2 C7B H7B3 109.5 . . ?
C9B N8B N7B 119.3(3) . . ?
C9B N8B Nd1 119.0(3) . . ?
N7B N8B Nd1 121.6(2) . . ?
N8B C9B C10B 115.8(4) . . ?
N8B C9B H9B 122.1 . . ?
C10B C9B H9B 122.1 . . ?
N14B C10B N11B 110.5(4) . . ?
N14B C10B C9B 124.5(4) . . ?
N11B C10B C9B 125.0(4) . . ?
C12B N11B C10B 106.9(3) . . ?
C12B N11B C11B 126.0(4) . . ?
C10B N11B C11B 127.1(4) . . ?
N11B C11B H11D 109.5 . . ?
N11B C11B H11E 109.5 . . ?
H11D C11B H11E 109.5 . . ?
N11B C11B H11F 109.5 . . ?
H11D C11B H11F 109.5 . . ?
H11E C11B H11F 109.5 . . ?
N11B C12B C13B 107.2(4) . . ?
N11B C12B H12B 126.4 . . ?
C13B C12B H12B 126.4 . . ?
C12B C13B N14B 109.2(4) . . ?
C12B C13B H13B 125.4 . . ?
N14B C13B H13B 125.4 . . ?
C10B N14B C13B 106.3(4) . . ?
C10B N14B Nd1 117.0(3) . . ?
C13B N14B Nd1 136.2(3) . . ?
O11C S1C O12C 116.9(2) . . ?
O11C S1C O13C 114.66(19) . . ?
O12C S1C O13C 113.6(2) . . ?
O11C S1C C1C 102.6(2) . . ?
O12C S1C C1C 103.9(2) . . ?
O13C S1C C1C 102.7(2) . . ?
S1C O13C Nd1 146.6(2) . . ?
F11C C1C F12C 108.5(4) . . ?
F11C C1C F13C 107.8(4) . . ?
F12C C1C F13C 107.7(4) . . ?
F11C C1C S1C 112.2(4) . . ?
F12C C1C S1C 111.4(3) . . ?
F13C C1C S1C 109.0(3) . . ?
O11D S1D O12D 116.6(2) . . ?
O11D S1D O13D 114.6(2) . . ?
O12D S1D O13D 113.4(2) . . ?
O11D S1D C1D 103.8(2) . . ?
O12D S1D C1D 104.6(3) . . ?
O13D S1D C1D 101.6(2) . . ?
S1D O13D Nd1 149.71(19) . . ?
F12D C1D F13D 107.4(5) . . ?
F12D C1D F11D 108.7(5) . . ?
F13D C1D F11D 106.9(5) . . ?
F12D C1D S1D 111.8(4) . . ?
F13D C1D S1D 112.6(4) . . ?
F11D C1D S1D 109.2(4) . . ?
O11E S1E O12E 116.9(2) . . ?
O11E S1E O13E 113.9(2) . . ?
O12E S1E O13E 114.33(19) . . ?
O11E S1E C1E 104.1(2) . . ?
O12E S1E C1E 101.9(2) . . ?
O13E S1E C1E 103.3(2) . . ?
S1E O13E Nd1 142.37(19) . . ?
F12E C1E F11E 107.5(5) . . ?
F12E C1E F13E 108.0(4) . . ?
F11E C1E F13E 106.9(5) . . ?
F12E C1E S1E 113.7(4) . . ?
F11E C1E S1E 111.0(4) . . ?
F13E C1E S1E 109.5(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6A N1A C2A N7A -176.9(4) . . . . ?
Nd1 N1A C2A N7A 4.9(5) . . . . ?
C6A N1A C2A C3A 2.1(6) . . . . ?
Nd1 N1A C2A C3A -176.0(3) . . . . ?
N1A C2A C3A C4A -2.1(6) . . . . ?
N7A C2A C3A C4A 176.9(4) . . . . ?
C2A C3A C4A C5A 0.6(7) . . . . ?
C3A C4A C5A C6A 0.6(7) . . . . ?
C2A N1A C6A C5A -0.8(6) . . . . ?
Nd1 N1A C6A C5A 177.5(3) . . . . ?
C4A C5A C6A N1A -0.5(7) . . . . ?
N1A C2A N7A N8A -4.5(5) . . . . ?
C3A C2A N7A N8A 176.5(4) . . . . ?
N1A C2A N7A C7A 178.5(4) . . . . ?
C3A C2A N7A C7A -0.5(6) . . . . ?
C2A N7A N8A C9A -176.1(4) . . . . ?
C7A N7A N8A C9A 1.0(6) . . . . ?
C2A N7A N8A Nd1 2.3(4) . . . . ?
C7A N7A N8A Nd1 179.5(3) . . . . ?
N7A N8A C9A C10A 179.6(4) . . . . ?
Nd1 N8A C9A C10A 1.1(5) . . . . ?
N8A C9A C10A N14A 4.5(7) . . . . ?
N8A C9A C10A N11A -170.8(4) . . . . ?
N14A C10A N11A C12A 0.3(5) . . . . ?
C9A C10A N11A C12A 176.1(4) . . . . ?
N14A C10A N11A C11A -174.5(5) . . . . ?
C9A C10A N11A C11A 1.4(7) . . . . ?
C10A N11A C12A C13A 0.2(5) . . . . ?
C11A N11A C12A C13A 175.1(5) . . . . ?
N11A C12A C13A N14A -0.5(6) . . . . ?
N11A C10A N14A C13A -0.6(5) . . . . ?
C9A C10A N14A C13A -176.5(4) . . . . ?
N11A C10A N14A Nd1 168.0(3) . . . . ?
C9A C10A N14A Nd1 -7.9(6) . . . . ?
C12A C13A N14A C10A 0.7(5) . . . . ?
C12A C13A N14A Nd1 -164.8(4) . . . . ?
C6B N1B C2B N7B -177.5(4) . . . . ?
Nd1 N1B C2B N7B -1.8(5) . . . . ?
C6B N1B C2B C3B -0.6(6) . . . . ?
Nd1 N1B C2B C3B 175.1(3) . . . . ?
N1B C2B C3B C4B 0.1(7) . . . . ?
N7B C2B C3B C4B 176.9(4) . . . . ?
C2B C3B C4B C5B 0.7(8) . . . . ?
C3B C4B C5B C6B -1.1(8) . . . . ?
C2B N1B C6B C5B 0.3(7) . . . . ?
Nd1 N1B C6B C5B -175.8(4) . . . . ?
C4B C5B C6B N1B 0.6(8) . . . . ?
N1B C2B N7B N8B 2.6(6) . . . . ?
C3B C2B N7B N8B -174.3(4) . . . . ?
N1B C2B N7B C7B -164.2(5) . . . . ?
C3B C2B N7B C7B 19.0(7) . . . . ?
C2B N7B N8B C9B -178.6(4) . . . . ?
C7B N7B N8B C9B -11.3(6) . . . . ?
C2B N7B N8B Nd1 -2.3(5) . . . . ?
C7B N7B N8B Nd1 165.0(3) . . . . ?
N7B N8B C9B C10B 177.6(4) . . . . ?
Nd1 N8B C9B C10B 1.2(5) . . . . ?
N8B C9B C10B N14B 1.5(7) . . . . ?
N8B C9B C10B N11B -174.4(4) . . . . ?
N14B C10B N11B C12B -0.8(5) . . . . ?
C9B C10B N11B C12B 175.7(4) . . . . ?
N14B C10B N11B C11B -178.8(5) . . . . ?
C9B C10B N11B C11B -2.3(7) . . . . ?
C10B N11B C12B C13B 1.0(6) . . . . ?
C11B N11B C12B C13B 179.0(5) . . . . ?
N11B C12B C13B N14B -0.8(6) . . . . ?
N11B C10B N14B C13B 0.3(5) . . . . ?
C9B C10B N14B C13B -176.2(4) . . . . ?
N11B C10B N14B Nd1 173.0(3) . . . . ?
C9B C10B N14B Nd1 -3.5(6) . . . . ?
C12B C13B N14B C10B 0.3(6) . . . . ?
C12B C13B N14B Nd1 -170.3(4) . . . . ?
O11C S1C O13C Nd1 44.3(5) . . . . ?
O12C S1C O13C Nd1 -93.7(4) . . . . ?
C1C S1C O13C Nd1 154.8(4) . . . . ?
O11C S1C C1C F11C -172.9(3) . . . . ?
O12C S1C C1C F11C -50.8(4) . . . . ?
O13C S1C C1C F11C 67.8(4) . . . . ?
O11C S1C C1C F12C 65.2(4) . . . . ?
O12C S1C C1C F12C -172.7(3) . . . . ?
O13C S1C C1C F12C -54.1(4) . . . . ?
O11C S1C C1C F13C -53.5(4) . . . . ?
O12C S1C C1C F13C 68.6(4) . . . . ?
O13C S1C C1C F13C -172.8(3) . . . . ?
O11D S1D O13D Nd1 -79.5(4) . . . . ?
O12D S1D O13D Nd1 57.7(4) . . . . ?
C1D S1D O13D Nd1 169.3(4) . . . . ?
O11D S1D C1D F12D -54.8(4) . . . . ?
O12D S1D C1D F12D -177.5(4) . . . . ?
O13D S1D C1D F12D 64.4(4) . . . . ?
O11D S1D C1D F13D -175.8(4) . . . . ?
O12D S1D C1D F13D 61.5(5) . . . . ?
O13D S1D C1D F13D -56.6(5) . . . . ?
O11D S1D C1D F11D 65.6(5) . . . . ?
O12D S1D C1D F11D -57.1(5) . . . . ?
O13D S1D C1D F11D -175.2(4) . . . . ?
O11E S1E O13E Nd1 59.9(4) . . . . ?
O12E S1E O13E Nd1 -78.1(3) . . . . ?
C1E S1E O13E Nd1 172.1(3) . . . . ?
O11E S1E C1E F12E 52.6(5) . . . . ?
O12E S1E C1E F12E 174.5(4) . . . . ?
O13E S1E C1E F12E -66.7(5) . . . . ?
O11E S1E C1E F11E 173.9(4) . . . . ?
O12E S1E C1E F11E -64.2(4) . . . . ?
O13E S1E C1E F11E 54.6(4) . . . . ?
O11E S1E C1E F13E -68.3(4) . . . . ?
O12E S1E C1E F13E 53.6(4) . . . . ?
O13E S1E C1E F13E 172.4(4) . . . . ?

_refine_diff_density_max         0.753
_refine_diff_density_min         -0.544
_refine_diff_density_rms         0.073

_shelxl_version_number           2013-4

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_07
_database_code_depnum_ccdc_archive 'CCDC 1052307'
_audit_update_record             
;
2016-01-10 deposited with the CCDC.	2024-07-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C25 H34 F3 N10 O5 S Tb, 2(C F3 O3 S)'
_chemical_formula_sum            'C27 H34 F9 N10 O11 S3 Tb'
_chemical_formula_weight         1100.74

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Tb Tb -0.1723 4.1537 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   10.9638(4)
_cell_length_b                   15.0249(7)
_cell_length_c                   26.8438(15)
_cell_angle_alpha                90
_cell_angle_beta                 99.705(5)
_cell_angle_gamma                90
_cell_volume                     4358.7(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(1)
_cell_measurement_reflns_used    6887
_cell_measurement_theta_min      3.4080
_cell_measurement_theta_max      28.2550

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.677
_exptl_crystal_F_000             2192
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.1
_exptl_absorpt_coefficient_mu    1.867
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.46567
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(1)
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Eos
_diffrn_detector_area_resol_mean 16.1544
_diffrn_measurement_method       ω-scan
_diffrn_reflns_number            18343
_diffrn_reflns_av_unetI/netI     0.0419
_diffrn_reflns_av_R_equivalents  0.0321
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         2.956
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        24.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             7646
_reflns_number_gt                6946
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlis Pro (Agilent Technologies (2011))'
_computing_cell_refinement       'CrysAlis Pro (Agilent Technologies (2011))'
_computing_data_reduction        'CrysAlis Pro (Agilent Technologies (2011))'
_computing_structure_solution    'SIR92 (Altomare et al., 1993)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Mercury (MacRae et al., 2009)'
_computing_publication_material  'SHELXL-2013 (Sheldrick, 2013)'

_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0383P)²+175.1329P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7646
_refine_ls_number_parameters     556
_refine_ls_number_restraints     276
_refine_ls_R_factor_all          0.1027
_refine_ls_R_factor_gt           0.0963
_refine_ls_wR_factor_ref         0.2088
_refine_ls_wR_factor_gt          0.2055
_refine_ls_goodness_of_fit_ref   1.142
_refine_ls_restrained_S_all      1.130
_refine_ls_shift/su_max          0.012
_refine_ls_shift/su_mean         0.000

# SQUEEZE RESULTS (APPEND TO CIF)
# Note: Data are Listed for all Voids in the P1 Unit Cell
# i.e. Centre of Gravity, Solvent Accessible Volume,
# Recovered number of Electrons in the Void and
# Details about the Squeezed Material
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.000 1.000 0.500 248 42 ' '
2 0.500 0.500 0.000 248 42 ' '
_platon_squeeze_details          
;
;

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Tb1 Tb 0.10097(4) 0.17959(3) 0.15092(2) 0.01324(17) Uani 1 1 d . . . . .
N1A N -0.0751(8) 0.1893(6) 0.0753(3) 0.018(2) Uani 1 1 d . U . . .
C2A C -0.1921(10) 0.1668(8) 0.0771(4) 0.019(2) Uani 1 1 d . U . . .
C3A C -0.2898(11) 0.1837(10) 0.0370(5) 0.030(3) Uani 1 1 d . U . . .
H3A H -0.3724 0.1672 0.0391 0.036 Uiso 1 1 calc R U . . .
C4A C -0.2618(13) 0.2249(11) -0.0055(5) 0.039(3) Uani 1 1 d . U . . .
H4A H -0.3255 0.2366 -0.0334 0.047 Uiso 1 1 calc R U . . .
C5A C -0.1408(12) 0.2496(10) -0.0079(5) 0.032(3) Uani 1 1 d . U . . .
H5A H -0.1201 0.2801 -0.0363 0.039 Uiso 1 1 calc R U . . .
C6A C -0.0529(11) 0.2278(9) 0.0327(4) 0.024(3) Uani 1 1 d . U . . .
H6A H 0.0307 0.2411 0.0305 0.029 Uiso 1 1 calc R U . . .
N7A N -0.2158(8) 0.1262(6) 0.1212(4) 0.018(2) Uani 1 1 d . U . . .
C71A C -0.3356(12) 0.0911(10) 0.1266(5) 0.034(3) Uani 1 1 d . U . . .
H71A H -0.3249 0.0344 0.1448 0.051 Uiso 1 1 calc R U . . .
H71B H -0.3851 0.0816 0.0931 0.051 Uiso 1 1 calc R U . . .
H71C H -0.3780 0.1335 0.1455 0.051 Uiso 1 1 calc R U . . .
N8A N -0.1204(8) 0.1276(6) 0.1610(3) 0.0137(19) Uani 1 1 d . U . . .
C9A C -0.1385(10) 0.0989(7) 0.2043(4) 0.017(2) Uani 1 1 d . U . . .
H9A H -0.2166 0.0769 0.2096 0.020 Uiso 1 1 calc R U . . .
C10A C -0.0314(10) 0.1024(7) 0.2448(4) 0.015(2) Uani 1 1 d . U . . .
N11A N -0.0297(8) 0.0770(6) 0.2931(4) 0.017(2) Uani 1 1 d . U . . .
C11A C -0.1365(11) 0.0463(9) 0.3141(5) 0.027(3) Uani 1 1 d . U . . .
H11A H -0.1989 0.0936 0.3110 0.041 Uiso 1 1 calc R U . . .
H11B H -0.1107 0.0312 0.3499 0.041 Uiso 1 1 calc R U . . .
H11C H -0.1718 -0.0064 0.2956 0.041 Uiso 1 1 calc R U . . .
C12A C 0.0885(11) 0.0922(8) 0.3186(4) 0.021(2) Uani 1 1 d . U . . .
H12A H 0.1179 0.0824 0.3536 0.025 Uiso 1 1 calc R U . . .
C13A C 0.1547(11) 0.1240(7) 0.2840(4) 0.018(2) Uani 1 1 d . U . . .
H13A H 0.2399 0.1395 0.2908 0.022 Uiso 1 1 calc R U . . .
N14A N 0.0794(8) 0.1304(6) 0.2376(4) 0.0150(19) Uani 1 1 d . U . . .
N1B N 0.2855(9) 0.2536(6) 0.2070(4) 0.019(2) Uani 1 1 d . U . . .
C2B C 0.3928(10) 0.2115(7) 0.2236(4) 0.016(2) Uani 1 1 d . U . . .
C3B C 0.4985(11) 0.2563(8) 0.2482(5) 0.027(3) Uani 1 1 d . U . . .
H3B H 0.5740 0.2254 0.2587 0.032 Uiso 1 1 calc R U . . .
C4B C 0.4899(13) 0.3453(9) 0.2566(5) 0.029(3) Uani 1 1 d . U . . .
H4B H 0.5604 0.3772 0.2727 0.035 Uiso 1 1 calc R U . . .
C5B C 0.3783(11) 0.3895(8) 0.2417(4) 0.022(3) Uani 1 1 d . U . . .
H5B H 0.3705 0.4510 0.2488 0.026 Uiso 1 1 calc R U . . .
C6B C 0.2801(11) 0.3424(7) 0.2167(4) 0.019(2) Uani 1 1 d . U . . .
H6B H 0.2046 0.3730 0.2055 0.023 Uiso 1 1 calc R U . . .
N7B N 0.3947(8) 0.1207(6) 0.2146(4) 0.018(2) Uani 1 1 d . U . . .
C71B C 0.4986(10) 0.0627(8) 0.2362(5) 0.022(3) Uani 1 1 d . U . . .
H71D H 0.4694 0.0175 0.2577 0.033 Uiso 1 1 calc R U . . .
H71E H 0.5635 0.0986 0.2564 0.033 Uiso 1 1 calc R U . . .
H71F H 0.5321 0.0335 0.2088 0.033 Uiso 1 1 calc R U . . .
N8B N 0.2910(8) 0.0851(6) 0.1877(4) 0.018(2) Uani 1 1 d . U . . .
C9B C 0.2889(11) -0.0001(8) 0.1778(5) 0.024(3) Uani 1 1 d . U . . .
H9B H 0.3582 -0.0375 0.1885 0.029 Uiso 1 1 calc R U . . .
C10B C 0.1736(10) -0.0342(8) 0.1493(4) 0.019(2) Uani 1 1 d . U . . .
N11B N 0.1505(10) -0.1198(7) 0.1352(4) 0.029(2) Uani 1 1 d . U . . .
C11B C 0.2388(12) -0.1936(8) 0.1447(6) 0.032(3) Uani 1 1 d . U . . .
H11D H 0.3059 -0.1844 0.1254 0.049 Uiso 1 1 calc R U . . .
H11E H 0.1964 -0.2497 0.1344 0.049 Uiso 1 1 calc R U . . .
H11F H 0.2731 -0.1960 0.1809 0.049 Uiso 1 1 calc R U . . .
C12B C 0.0304(12) -0.1245(9) 0.1118(5) 0.029(3) Uani 1 1 d . U . . .
H12B H -0.0133 -0.1763 0.0986 0.035 Uiso 1 1 calc R U . . .
C13B C -0.0147(11) -0.0386(8) 0.1111(5) 0.028(3) Uani 1 1 d . U . . .
H13B H -0.0961 -0.0211 0.0964 0.033 Uiso 1 1 calc R U . . .
N14B N 0.0742(9) 0.0174(6) 0.1347(4) 0.021(2) Uani 1 1 d . U . . .
S1C S 0.3218(5) 0.1198(3) 0.06437(19) 0.0583(12) Uani 1 1 d . U . . .
O11C O 0.4081(9) 0.1788(7) 0.0537(4) 0.038(2) Uani 1 1 d . U . . .
O12C O 0.3712(14) 0.0283(11) 0.0840(6) 0.083(4) Uani 1 1 d . U . . .
O13C O 0.2200(8) 0.1544(6) 0.0870(3) 0.0250(19) Uani 1 1 d . U . . .
C1C C 0.242(2) 0.0829(16) 0.0065(9) 0.079(6) Uani 1 1 d . U . . .
F11C F 0.1548(11) 0.0155(8) 0.0120(4) 0.071(3) Uani 1 1 d . U . . .
F12C F 0.1933(12) 0.1653(9) -0.0169(5) 0.087(4) Uani 1 1 d . U . . .
F13C F 0.3176(10) 0.0368(8) -0.0210(4) 0.069(3) Uani 1 1 d . U . . .
O1D O -0.0099(7) 0.2986(5) 0.1855(3) 0.0168(16) Uani 1 1 d . . . . .
H1D H -0.0021 0.2982 0.2166 0.025 Uiso 1 1 d R U . . .
C1D C -0.1289(13) 0.3410(9) 0.1630(6) 0.037(3) Uani 1 1 d . U . . .
H1D1 H -0.1352 0.3432 0.1261 0.056 Uiso 1 1 calc R U . . .
H1D2 H -0.1322 0.4016 0.1762 0.056 Uiso 1 1 calc R U . . .
H1D3 H -0.1978 0.3061 0.1717 0.056 Uiso 1 1 calc R U . . .
O1E O 0.1329(7) 0.3240(6) 0.1118(3) 0.0229(18) Uani 1 1 d . . . . .
H1E H 0.1058 0.3651 0.1277 0.034 Uiso 1 1 d R U . . .
C1E C 0.2308(13) 0.3576(9) 0.0872(6) 0.035(3) Uani 1 1 d . U . . .
H1E1 H 0.2269 0.3286 0.0543 0.053 Uiso 1 1 calc R U . . .
H1E2 H 0.3110 0.3450 0.1083 0.053 Uiso 1 1 calc R U . . .
H1E3 H 0.2211 0.4220 0.0824 0.053 Uiso 1 1 calc R U . . .
S1F S 0.4380(3) 0.0697(2) 0.37458(13) 0.0311(7) Uani 1 1 d . . . . .
O11F O 0.3438(9) 0.0870(7) 0.4050(4) 0.044(3) Uani 1 1 d . . . . .
O12F O 0.4627(10) 0.1423(6) 0.3437(4) 0.041(2) Uani 1 1 d . . . . .
O13F O 0.4357(7) -0.0148(5) 0.3506(3) 0.0144(16) Uani 1 1 d . U . . .
C1F C 0.5786(16) 0.0628(12) 0.4211(7) 0.052(4) Uani 1 1 d . U . . .
F11F F 0.6751(8) 0.0486(8) 0.3955(5) 0.066(3) Uani 1 1 d . . . . .
F12F F 0.5960(9) 0.1350(8) 0.4492(4) 0.072(3) Uani 1 1 d . . . . .
F13F F 0.5712(10) -0.0058(8) 0.4531(4) 0.071(3) Uani 1 1 d . . . . .
S1G S 0.8593(3) 0.3306(2) 0.29564(11) 0.0219(6) Uani 1 1 d . . . . .
O11G O 0.7921(8) 0.2527(6) 0.2749(3) 0.028(2) Uani 1 1 d . . . . .
O12G O 0.9847(8) 0.3363(6) 0.2844(3) 0.0265(19) Uani 1 1 d . . . . .
O13G O 0.7920(8) 0.4124(6) 0.2899(3) 0.0245(19) Uani 1 1 d . U . . .
C1G C 0.8855(13) 0.3116(10) 0.3640(5) 0.034(3) Uani 1 1 d . U . . .
F11G F 0.9482(8) 0.2363(5) 0.3763(3) 0.040(2) Uani 1 1 d . . . . .
F12G F 0.7784(8) 0.3070(7) 0.3806(3) 0.053(2) Uani 1 1 d . . . . .
F13G F 0.9518(8) 0.3776(6) 0.3884(3) 0.042(2) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Tb1 O13C 2.354(8) . ?
Tb1 O1D 2.433(7) . ?
Tb1 O1E 2.462(8) . ?
Tb1 N14B 2.484(9) . ?
Tb1 N14A 2.491(9) . ?
Tb1 N1A 2.559(9) . ?
Tb1 N1B 2.562(9) . ?
Tb1 N8B 2.577(9) . ?
Tb1 N8A 2.606(9) . ?
N1A C2A 1.335(14) . ?
N1A C6A 1.341(15) . ?
C2A N7A 1.394(15) . ?
C2A C3A 1.409(16) . ?
C3A C4A 1.378(19) . ?
C3A H3A 0.9500 . ?
C4A C5A 1.389(19) . ?
C4A H4A 0.9500 . ?
C5A C6A 1.365(18) . ?
C5A H5A 0.9500 . ?
C6A H6A 0.9500 . ?
N7A N8A 1.363(13) . ?
N7A C71A 1.444(15) . ?
C71A H71A 0.9800 . ?
C71A H71B 0.9800 . ?
C71A H71C 0.9800 . ?
N8A C9A 1.286(14) . ?
C9A C10A 1.461(15) . ?
C9A H9A 0.9500 . ?
C10A N14A 1.330(14) . ?
C10A N11A 1.350(14) . ?
N11A C12A 1.379(14) . ?
N11A C11A 1.458(14) . ?
C11A H11A 0.9800 . ?
C11A H11B 0.9800 . ?
C11A H11C 0.9800 . ?
C12A C13A 1.359(17) . ?
C12A H12A 0.9500 . ?
C13A N14A 1.377(14) . ?
C13A H13A 0.9500 . ?
N1B C2B 1.344(14) . ?
N1B C6B 1.364(15) . ?
C2B N7B 1.386(15) . ?
C2B C3B 1.405(16) . ?
C3B C4B 1.361(18) . ?
C3B H3B 0.9500 . ?
C4B C5B 1.391(18) . ?
C4B H4B 0.9500 . ?
C5B C6B 1.367(17) . ?
C5B H5B 0.9500 . ?
C6B H6B 0.9500 . ?
N7B N8B 1.351(13) . ?
N7B C71B 1.474(14) . ?
C71B H71D 0.9800 . ?
C71B H71E 0.9800 . ?
C71B H71F 0.9800 . ?
N8B C9B 1.307(15) . ?
C9B C10B 1.456(17) . ?
C9B H9B 0.9500 . ?
C10B N14B 1.341(15) . ?
C10B N11B 1.352(15) . ?
N11B C12B 1.362(17) . ?
N11B C11B 1.466(16) . ?
C11B H11D 0.9800 . ?
C11B H11E 0.9800 . ?
C11B H11F 0.9800 . ?
C12B C13B 1.382(18) . ?
C12B H12B 0.9500 . ?
C13B N14B 1.360(15) . ?
C13B H13B 0.9500 . ?
S1C O11C 1.362(11) . ?
S1C O13C 1.455(9) . ?
S1C O12C 1.537(16) . ?
S1C C1C 1.74(2) . ?
C1C F13C 1.38(2) . ?
C1C F11C 1.42(3) . ?
C1C F12C 1.45(3) . ?
O1D C1D 1.486(16) . ?
O1D H1D 0.8251 . ?
C1D H1D1 0.9800 . ?
C1D H1D2 0.9800 . ?
C1D H1D3 0.9800 . ?
O1E C1E 1.442(14) . ?
O1E H1E 0.8343 . ?
C1E H1E1 0.9800 . ?
C1E H1E2 0.9800 . ?
C1E H1E3 0.9800 . ?
S1F O12F 1.424(10) . ?
S1F O13F 1.422(8) . ?
S1F O11F 1.443(10) . ?
S1F C1F 1.815(18) . ?
C1F F12F 1.32(2) . ?
C1F F11F 1.372(19) . ?
C1F F13F 1.35(2) . ?
S1G O13G 1.429(9) . ?
S1G O11G 1.443(9) . ?
S1G O12G 1.459(9) . ?
S1G C1G 1.830(14) . ?
C1G F11G 1.335(16) . ?
C1G F12G 1.327(15) . ?
C1G F13G 1.336(16) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O13C Tb1 O1D 140.4(3) . . ?
O13C Tb1 O1E 72.2(3) . . ?
O1D Tb1 O1E 68.3(3) . . ?
O13C Tb1 N14B 77.2(3) . . ?
O1D Tb1 N14B 137.4(3) . . ?
O1E Tb1 N14B 144.2(3) . . ?
O13C Tb1 N14A 141.7(3) . . ?
O1D Tb1 N14A 74.3(3) . . ?
O1E Tb1 N14A 134.7(3) . . ?
N14B Tb1 N14A 81.1(3) . . ?
O13C Tb1 N1A 82.4(3) . . ?
O1D Tb1 N1A 84.4(3) . . ?
O1E Tb1 N1A 75.7(3) . . ?
N14B Tb1 N1A 82.3(3) . . ?
N14A Tb1 N1A 125.5(3) . . ?
O13C Tb1 N1B 91.0(3) . . ?
O1D Tb1 N1B 81.5(3) . . ?
O1E Tb1 N1B 73.3(3) . . ?
N14B Tb1 N1B 125.9(3) . . ?
N14A Tb1 N1B 76.7(3) . . ?
N1A Tb1 N1B 148.9(3) . . ?
O13C Tb1 N8B 71.3(3) . . ?
O1D Tb1 N8B 133.0(3) . . ?
O1E Tb1 N8B 119.1(3) . . ?
N14B Tb1 N8B 65.8(3) . . ?
N14A Tb1 N8B 71.1(3) . . ?
N1A Tb1 N8B 142.1(3) . . ?
N1B Tb1 N8B 60.4(3) . . ?
O13C Tb1 N8A 131.9(3) . . ?
O1D Tb1 N8A 69.3(3) . . ?
O1E Tb1 N8A 120.7(3) . . ?
N14B Tb1 N8A 68.9(3) . . ?
N14A Tb1 N8A 65.0(3) . . ?
N1A Tb1 N8A 60.5(3) . . ?
N1B Tb1 N8A 136.5(3) . . ?
N8B Tb1 N8A 120.1(3) . . ?
C2A N1A C6A 117.0(10) . . ?
C2A N1A Tb1 123.9(7) . . ?
C6A N1A Tb1 118.7(7) . . ?
N1A C2A N7A 117.4(10) . . ?
N1A C2A C3A 122.5(11) . . ?
N7A C2A C3A 120.2(10) . . ?
C4A C3A C2A 117.9(12) . . ?
C4A C3A H3A 121.0 . . ?
C2A C3A H3A 121.0 . . ?
C3A C4A C5A 120.3(13) . . ?
C3A C4A H4A 119.8 . . ?
C5A C4A H4A 119.8 . . ?
C6A C5A C4A 116.8(13) . . ?
C6A C5A H5A 121.6 . . ?
C4A C5A H5A 121.6 . . ?
N1A C6A C5A 125.3(11) . . ?
N1A C6A H6A 117.3 . . ?
C5A C6A H6A 117.3 . . ?
N8A N7A C2A 115.4(9) . . ?
N8A N7A C71A 121.2(9) . . ?
C2A N7A C71A 123.1(10) . . ?
N7A C71A H71A 109.5 . . ?
N7A C71A H71B 109.5 . . ?
H71A C71A H71B 109.5 . . ?
N7A C71A H71C 109.5 . . ?
H71A C71A H71C 109.5 . . ?
H71B C71A H71C 109.5 . . ?
C9A N8A N7A 119.1(9) . . ?
C9A N8A Tb1 118.9(7) . . ?
N7A N8A Tb1 121.9(6) . . ?
N8A C9A C10A 115.6(10) . . ?
N8A C9A H9A 122.2 . . ?
C10A C9A H9A 122.2 . . ?
N14A C10A N11A 111.3(10) . . ?
N14A C10A C9A 122.9(10) . . ?
N11A C10A C9A 125.8(10) . . ?
C10A N11A C12A 106.9(9) . . ?
C10A N11A C11A 125.4(10) . . ?
C12A N11A C11A 127.6(10) . . ?
N11A C11A H11A 109.5 . . ?
N11A C11A H11B 109.5 . . ?
H11A C11A H11B 109.5 . . ?
N11A C11A H11C 109.5 . . ?
H11A C11A H11C 109.5 . . ?
H11B C11A H11C 109.5 . . ?
C13A C12A N11A 106.5(10) . . ?
C13A C12A H12A 126.7 . . ?
N11A C12A H12A 126.7 . . ?
C12A C13A N14A 109.6(10) . . ?
C12A C13A H13A 125.2 . . ?
N14A C13A H13A 125.2 . . ?
C10A N14A C13A 105.7(9) . . ?
C10A N14A Tb1 117.5(7) . . ?
C13A N14A Tb1 136.8(7) . . ?
C2B N1B C6B 117.4(10) . . ?
C2B N1B Tb1 123.5(7) . . ?
C6B N1B Tb1 118.8(8) . . ?
N1B C2B N7B 116.2(10) . . ?
N1B C2B C3B 122.6(10) . . ?
N7B C2B C3B 121.2(10) . . ?
C4B C3B C2B 118.2(12) . . ?
C4B C3B H3B 120.9 . . ?
C2B C3B H3B 120.9 . . ?
C3B C4B C5B 120.3(13) . . ?
C3B C4B H4B 119.9 . . ?
C5B C4B H4B 119.9 . . ?
C6B C5B C4B 118.4(12) . . ?
C6B C5B H5B 120.8 . . ?
C4B C5B H5B 120.8 . . ?
N1B C6B C5B 123.0(11) . . ?
N1B C6B H6B 118.5 . . ?
C5B C6B H6B 118.5 . . ?
N8B N7B C2B 116.6(9) . . ?
N8B N7B C71B 120.0(9) . . ?
C2B N7B C71B 123.1(9) . . ?
N7B C71B H71D 109.5 . . ?
N7B C71B H71E 109.5 . . ?
H71D C71B H71E 109.5 . . ?
N7B C71B H71F 109.5 . . ?
H71D C71B H71F 109.5 . . ?
H71E C71B H71F 109.5 . . ?
C9B N8B N7B 118.8(10) . . ?
C9B N8B Tb1 118.4(8) . . ?
N7B N8B Tb1 122.6(7) . . ?
N8B C9B C10B 115.9(11) . . ?
N8B C9B H9B 122.1 . . ?
C10B C9B H9B 122.1 . . ?
N14B C10B N11B 111.3(10) . . ?
N14B C10B C9B 122.7(10) . . ?
N11B C10B C9B 125.9(11) . . ?
C10B N11B C12B 107.4(11) . . ?
C10B N11B C11B 125.7(10) . . ?
C12B N11B C11B 126.9(11) . . ?
N11B C11B H11D 109.5 . . ?
N11B C11B H11E 109.5 . . ?
H11D C11B H11E 109.5 . . ?
N11B C11B H11F 109.5 . . ?
H11D C11B H11F 109.5 . . ?
H11E C11B H11F 109.5 . . ?
N11B C12B C13B 105.9(11) . . ?
N11B C12B H12B 127.1 . . ?
C13B C12B H12B 127.1 . . ?
N14B C13B C12B 110.2(11) . . ?
N14B C13B H13B 124.9 . . ?
C12B C13B H13B 124.9 . . ?
C10B N14B C13B 105.2(10) . . ?
C10B N14B Tb1 116.7(7) . . ?
C13B N14B Tb1 137.9(8) . . ?
O11C S1C O13C 117.7(6) . . ?
O11C S1C O12C 115.9(8) . . ?
O13C S1C O12C 115.3(7) . . ?
O11C S1C C1C 106.4(9) . . ?
O13C S1C C1C 100.5(9) . . ?
O12C S1C C1C 96.7(10) . . ?
S1C O13C Tb1 157.1(6) . . ?
F13C C1C F11C 99.9(17) . . ?
F13C C1C F12C 114.0(18) . . ?
F11C C1C F12C 116.5(18) . . ?
F13C C1C S1C 112.4(16) . . ?
F11C C1C S1C 112.4(15) . . ?
F12C C1C S1C 102.1(15) . . ?
C1D O1D Tb1 128.3(7) . . ?
C1D O1D H1D 110.4 . . ?
Tb1 O1D H1D 114.1 . . ?
O1D C1D H1D1 109.5 . . ?
O1D C1D H1D2 109.5 . . ?
H1D1 C1D H1D2 109.5 . . ?
O1D C1D H1D3 109.5 . . ?
H1D1 C1D H1D3 109.5 . . ?
H1D2 C1D H1D3 109.5 . . ?
C1E O1E Tb1 132.4(8) . . ?
C1E O1E H1E 109.4 . . ?
Tb1 O1E H1E 110.2 . . ?
O1E C1E H1E1 109.5 . . ?
O1E C1E H1E2 109.5 . . ?
H1E1 C1E H1E2 109.5 . . ?
O1E C1E H1E3 109.5 . . ?
H1E1 C1E H1E3 109.5 . . ?
H1E2 C1E H1E3 109.5 . . ?
O12F S1F O13F 114.3(6) . . ?
O12F S1F O11F 114.6(6) . . ?
O13F S1F O11F 117.2(6) . . ?
O12F S1F C1F 102.8(8) . . ?
O13F S1F C1F 102.0(7) . . ?
O11F S1F C1F 103.1(7) . . ?
F12F C1F F11F 111.5(15) . . ?
F12F C1F F13F 106.3(14) . . ?
F11F C1F F13F 109.5(14) . . ?
F12F C1F S1F 111.8(12) . . ?
F11F C1F S1F 107.6(12) . . ?
F13F C1F S1F 110.2(12) . . ?
O13G S1G O11G 115.8(5) . . ?
O13G S1G O12G 114.5(5) . . ?
O11G S1G O12G 113.9(5) . . ?
O13G S1G C1G 103.5(6) . . ?
O11G S1G C1G 104.1(6) . . ?
O12G S1G C1G 102.9(6) . . ?
F11G C1G F12G 108.7(12) . . ?
F11G C1G F13G 107.1(11) . . ?
F12G C1G F13G 108.2(11) . . ?
F11G C1G S1G 111.5(9) . . ?
F12G C1G S1G 110.3(10) . . ?
F13G C1G S1G 110.9(10) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6A N1A C2A N7A 179.6(10) . . . . ?
Tb1 N1A C2A N7A -7.7(14) . . . . ?
C6A N1A C2A C3A -1.3(17) . . . . ?
Tb1 N1A C2A C3A 171.5(9) . . . . ?
N1A C2A C3A C4A 0(2) . . . . ?
N7A C2A C3A C4A 179.3(12) . . . . ?
C2A C3A C4A C5A -1(2) . . . . ?
C3A C4A C5A C6A 2(2) . . . . ?
C2A N1A C6A C5A 3.3(19) . . . . ?
Tb1 N1A C6A C5A -169.9(11) . . . . ?
C4A C5A C6A N1A -4(2) . . . . ?
N1A C2A N7A N8A 10.8(15) . . . . ?
C3A C2A N7A N8A -168.4(11) . . . . ?
N1A C2A N7A C71A -174.2(11) . . . . ?
C3A C2A N7A C71A 6.7(18) . . . . ?
C2A N7A N8A C9A 173.6(10) . . . . ?
C71A N7A N8A C9A -1.5(16) . . . . ?
C2A N7A N8A Tb1 -9.4(12) . . . . ?
C71A N7A N8A Tb1 175.4(9) . . . . ?
N7A N8A C9A C10A 179.7(9) . . . . ?
Tb1 N8A C9A C10A 2.7(12) . . . . ?
N8A C9A C10A N14A -2.2(16) . . . . ?
N8A C9A C10A N11A 179.1(10) . . . . ?
N14A C10A N11A C12A 1.9(13) . . . . ?
C9A C10A N11A C12A -179.3(10) . . . . ?
N14A C10A N11A C11A 177.4(10) . . . . ?
C9A C10A N11A C11A -3.8(18) . . . . ?
C10A N11A C12A C13A -1.7(12) . . . . ?
C11A N11A C12A C13A -177.2(11) . . . . ?
N11A C12A C13A N14A 1.0(13) . . . . ?
N11A C10A N14A C13A -1.2(12) . . . . ?
C9A C10A N14A C13A 180.0(10) . . . . ?
N11A C10A N14A Tb1 179.4(7) . . . . ?
C9A C10A N14A Tb1 0.5(13) . . . . ?
C12A C13A N14A C10A 0.1(12) . . . . ?
C12A C13A N14A Tb1 179.3(8) . . . . ?
C6B N1B C2B N7B 178.1(10) . . . . ?
Tb1 N1B C2B N7B -8.3(14) . . . . ?
C6B N1B C2B C3B -2.8(17) . . . . ?
Tb1 N1B C2B C3B 170.7(9) . . . . ?
N1B C2B C3B C4B 2.0(19) . . . . ?
N7B C2B C3B C4B -179.0(12) . . . . ?
C2B C3B C4B C5B 0.9(19) . . . . ?
C3B C4B C5B C6B -2.8(19) . . . . ?
C2B N1B C6B C5B 0.7(16) . . . . ?
Tb1 N1B C6B C5B -173.1(9) . . . . ?
C4B C5B C6B N1B 2.0(18) . . . . ?
N1B C2B N7B N8B 3.5(15) . . . . ?
C3B C2B N7B N8B -175.6(11) . . . . ?
N1B C2B N7B C71B -171.5(10) . . . . ?
C3B C2B N7B C71B 9.4(17) . . . . ?
C2B N7B N8B C9B 179.2(10) . . . . ?
C71B N7B N8B C9B -5.6(16) . . . . ?
C2B N7B N8B Tb1 2.7(13) . . . . ?
C71B N7B N8B Tb1 177.8(8) . . . . ?
N7B N8B C9B C10B 179.1(10) . . . . ?
Tb1 N8B C9B C10B -4.1(14) . . . . ?
N8B C9B C10B N14B -1.2(17) . . . . ?
N8B C9B C10B N11B -179.5(11) . . . . ?
N14B C10B N11B C12B -1.8(14) . . . . ?
C9B C10B N11B C12B 176.7(11) . . . . ?
N14B C10B N11B C11B 179.6(12) . . . . ?
C9B C10B N11B C11B -2(2) . . . . ?
C10B N11B C12B C13B 1.9(15) . . . . ?
C11B N11B C12B C13B -179.5(13) . . . . ?
N11B C12B C13B N14B -1.5(15) . . . . ?
N11B C10B N14B C13B 0.8(14) . . . . ?
C9B C10B N14B C13B -177.7(11) . . . . ?
N11B C10B N14B Tb1 -175.4(8) . . . . ?
C9B C10B N14B Tb1 6.0(15) . . . . ?
C12B C13B N14B C10B 0.5(15) . . . . ?
C12B C13B N14B Tb1 175.5(9) . . . . ?
O11C S1C O13C Tb1 -108.6(14) . . . . ?
O12C S1C O13C Tb1 33.9(17) . . . . ?
C1C S1C O13C Tb1 136.5(15) . . . . ?
O11C S1C C1C F13C 63.8(17) . . . . ?
O13C S1C C1C F13C -173.1(14) . . . . ?
O12C S1C C1C F13C -55.7(17) . . . . ?
O11C S1C C1C F11C 175.6(14) . . . . ?
O13C S1C C1C F11C -61.3(16) . . . . ?
O12C S1C C1C F11C 56.1(17) . . . . ?
O11C S1C C1C F12C -58.8(15) . . . . ?
O13C S1C C1C F12C 64.3(14) . . . . ?
O12C S1C C1C F12C -178.3(13) . . . . ?
O12F S1F C1F F12F 63.6(14) . . . . ?
O13F S1F C1F F12F -177.8(12) . . . . ?
O11F S1F C1F F12F -55.8(14) . . . . ?
O12F S1F C1F F11F -59.1(13) . . . . ?
O13F S1F C1F F11F 59.6(13) . . . . ?
O11F S1F C1F F11F -178.5(11) . . . . ?
O12F S1F C1F F13F -178.3(11) . . . . ?
O13F S1F C1F F13F -59.7(12) . . . . ?
O11F S1F C1F F13F 62.2(13) . . . . ?
O13G S1G C1G F11G 179.9(9) . . . . ?
O11G S1G C1G F11G 58.4(10) . . . . ?
O12G S1G C1G F11G -60.7(11) . . . . ?
O13G S1G C1G F12G 59.0(11) . . . . ?
O11G S1G C1G F12G -62.5(11) . . . . ?
O12G S1G C1G F12G 178.4(10) . . . . ?
O13G S1G C1G F13G -60.9(10) . . . . ?
O11G S1G C1G F13G 177.7(9) . . . . ?
O12G S1G C1G F13G 58.6(10) . . . . ?

_refine_diff_density_max         9.532
_refine_diff_density_min         -3.599
_refine_diff_density_rms         0.246

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_LHBr-
_database_code_depnum_ccdc_archive 'CCDC 2338931'
loop_
_audit_author_name
_audit_author_address
'Maciej Kubicki'
;Adam Mickiewicz University
Poland
;
_audit_update_record             
;
2024-03-08 deposited with the CCDC.	2024-07-03 downloaded from the CCDC.
;

_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C11 H14 N5, C H4 O, Br'
_chemical_formula_sum            'C12 H18 Br N5 O'
_chemical_formula_weight         328.22

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.1754(4)
_cell_length_b                   9.5801(5)
_cell_length_c                   11.4950(6)
_cell_angle_alpha                74.019(5)
_cell_angle_beta                 71.999(5)
_cell_angle_gamma                73.388(5)
_cell_volume                     704.82(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    130(1)
_cell_measurement_reflns_used    4394
_cell_measurement_theta_min      4.9180
_cell_measurement_theta_max      75.5073

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.547
_exptl_crystal_F_000             336
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.08
_exptl_absorpt_coefficient_mu    3.990
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.34761
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21t (release 14-08-2012 CrysAlis171 .NET)
(compiled Aug 14 2012,18:12:40)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?

_diffrn_ambient_temperature      130(1)
_diffrn_radiation_wavelength     1.5418
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_source         'SuperNova (Cu) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'SuperNova, Single source at offset), Atlas'
_diffrn_detector_area_resol_mean 10.5357
_diffrn_reflns_number            4875
_diffrn_reflns_av_unetI/netI     0.0365
_diffrn_reflns_av_R_equivalents  0.0555
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         4.922
_diffrn_reflns_theta_max         75.693
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.954
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.954
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.954
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             2784
_reflns_number_gt                2751
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21t (release 14-08-2012 CrysAlis171 .NET)
(compiled Aug 14 2012,18:12:40)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21t (release 14-08-2012 CrysAlis171 .NET)
(compiled Aug 14 2012,18:12:40)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21t (release 14-08-2012 CrysAlis171 .NET)
(compiled Aug 14 2012,18:12:40)
;
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_molecular_graphics    'Mercury (MacRae et al., 2009)'
_computing_publication_material  'SHELXL (Sheldrick, 2015)'

_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0971P)²+0.3325P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     .
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2784
_refine_ls_number_parameters     183
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0468
_refine_ls_R_factor_gt           0.0464
_refine_ls_wR_factor_ref         0.1258
_refine_ls_wR_factor_gt          0.1253
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_restrained_S_all      1.093
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.0348(3) 0.7230(2) 0.5182(2) 0.0150(4) Uani 1 1 d . . . . .
H1 H 0.087(6) 0.724(4) 0.435(4) 0.028(10) Uiso 1 1 d . . . . .
C2 C 0.0647(3) 0.6119(3) 0.6162(2) 0.0136(4) Uani 1 1 d . . . . .
N3 N -0.0548(3) 0.6587(2) 0.7202(2) 0.0148(4) Uani 1 1 d . . . . .
C31 C -0.0769(4) 0.5679(3) 0.8474(2) 0.0193(5) Uani 1 1 d . . . . .
H31A H -0.137344 0.485291 0.854314 0.029 Uiso 1 1 calc R U . . .
H31B H -0.163580 0.629477 0.907436 0.029 Uiso 1 1 calc R U . . .
H31C H 0.055416 0.528228 0.865367 0.029 Uiso 1 1 calc R U . . .
C4 C -0.1625(4) 0.8022(3) 0.6864(3) 0.0181(5) Uani 1 1 d . . . . .
H4 H -0.257520 0.861863 0.741498 0.022 Uiso 1 1 calc R U . . .
C5 C -0.1071(4) 0.8415(3) 0.5604(3) 0.0178(5) Uani 1 1 d . . . . .
H5 H -0.156599 0.933523 0.510419 0.021 Uiso 1 1 calc R U . . .
C6 C 0.2007(4) 0.4679(3) 0.6136(2) 0.0145(5) Uani 1 1 d . . . . .
H6 H 0.214507 0.395930 0.687787 0.017 Uiso 1 1 calc R U . . .
N7 N 0.3026(3) 0.4431(2) 0.50390(19) 0.0134(4) Uani 1 1 d . . . . .
N8 N 0.4297(3) 0.3109(2) 0.49507(19) 0.0148(4) Uani 1 1 d . . . . .
C81 C 0.4475(4) 0.1930(3) 0.6050(2) 0.0200(5) Uani 1 1 d . . . . .
H81A H 0.515502 0.219728 0.655071 0.030 Uiso 1 1 calc R U . . .
H81B H 0.525781 0.099816 0.578758 0.030 Uiso 1 1 calc R U . . .
H81C H 0.313355 0.180123 0.655186 0.030 Uiso 1 1 calc R U . . .
C9 C 0.5335(3) 0.2905(3) 0.3731(2) 0.0131(5) Uani 1 1 d . . . . .
N10 N 0.6613(3) 0.1584(2) 0.3648(2) 0.0161(4) Uani 1 1 d . . . . .
C11 C 0.7560(4) 0.1336(3) 0.2490(3) 0.0187(5) Uani 1 1 d . . . . .
H11 H 0.846561 0.040399 0.241661 0.022 Uiso 1 1 calc R U . . .
C12 C 0.7305(4) 0.2343(3) 0.1406(2) 0.0215(5) Uani 1 1 d . . . . .
H12 H 0.798007 0.210677 0.060885 0.026 Uiso 1 1 calc R U . . .
C13 C 0.6015(4) 0.3724(3) 0.1523(2) 0.0198(5) Uani 1 1 d . . . . .
H13 H 0.581651 0.445763 0.079792 0.024 Uiso 1 1 calc R U . . .
C14 C 0.5025(4) 0.4025(3) 0.2698(2) 0.0164(5) Uani 1 1 d . . . . .
H14 H 0.416033 0.496543 0.279539 0.020 Uiso 1 1 calc R U . . .
Br1 Br 0.17737(3) 0.78472(2) 0.21455(2) 0.01863(16) Uani 1 1 d . . . . .
C1A C 0.7158(4) 0.8678(3) 0.0592(3) 0.0275(6) Uani 1 1 d . . . . .
H1AA H 0.718242 0.906071 -0.029426 0.041 Uiso 1 1 calc R U . . .
H1AB H 0.847370 0.860940 0.071847 0.041 Uiso 1 1 calc R U . . .
H1AC H 0.612776 0.935342 0.108931 0.041 Uiso 1 1 calc R U . . .
O1A O 0.6711(3) 0.7250(3) 0.0973(2) 0.0337(5) Uani 1 1 d . . . . .
H1A H 0.534(8) 0.739(6) 0.113(5) 0.054(14) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C2 1.345(3) . ?
N1 C5 1.377(3) . ?
N1 H1 0.91(4) . ?
C2 N3 1.344(3) . ?
C2 C6 1.446(3) . ?
N3 C4 1.387(3) . ?
N3 C31 1.468(3) . ?
C31 H31A 0.9800 . ?
C31 H31B 0.9800 . ?
C31 H31C 0.9800 . ?
C4 C5 1.351(4) . ?
C4 H4 0.9500 . ?
C5 H5 0.9500 . ?
C6 N7 1.295(3) . ?
C6 H6 0.9500 . ?
N7 N8 1.341(3) . ?
N8 C9 1.408(3) . ?
N8 C81 1.456(3) . ?
C81 H81A 0.9800 . ?
C81 H81B 0.9800 . ?
C81 H81C 0.9800 . ?
C9 N10 1.342(3) . ?
C9 C14 1.391(3) . ?
N10 C11 1.346(3) . ?
C11 C12 1.377(4) . ?
C11 H11 0.9500 . ?
C12 C13 1.395(4) . ?
C12 H12 0.9500 . ?
C13 C14 1.383(4) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C1A O1A 1.415(4) . ?
C1A H1AA 0.9800 . ?
C1A H1AB 0.9800 . ?
C1A H1AC 0.9800 . ?
O1A H1A 0.92(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N1 C5 109.3(2) . . ?
C2 N1 H1 129(3) . . ?
C5 N1 H1 122(3) . . ?
N3 C2 N1 107.5(2) . . ?
N3 C2 C6 125.1(2) . . ?
N1 C2 C6 127.4(2) . . ?
C2 N3 C4 108.8(2) . . ?
C2 N3 C31 125.1(2) . . ?
C4 N3 C31 126.0(2) . . ?
N3 C31 H31A 109.5 . . ?
N3 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
N3 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C5 C4 N3 107.3(2) . . ?
C5 C4 H4 126.4 . . ?
N3 C4 H4 126.4 . . ?
C4 C5 N1 107.1(2) . . ?
C4 C5 H5 126.4 . . ?
N1 C5 H5 126.4 . . ?
N7 C6 C2 115.9(2) . . ?
N7 C6 H6 122.0 . . ?
C2 C6 H6 122.0 . . ?
C6 N7 N8 118.8(2) . . ?
N7 N8 C9 115.9(2) . . ?
N7 N8 C81 121.5(2) . . ?
C9 N8 C81 122.4(2) . . ?
N8 C81 H81A 109.5 . . ?
N8 C81 H81B 109.5 . . ?
H81A C81 H81B 109.5 . . ?
N8 C81 H81C 109.5 . . ?
H81A C81 H81C 109.5 . . ?
H81B C81 H81C 109.5 . . ?
N10 C9 C14 123.5(2) . . ?
N10 C9 N8 115.6(2) . . ?
C14 C9 N8 120.8(2) . . ?
C9 N10 C11 116.8(2) . . ?
N10 C11 C12 124.4(2) . . ?
N10 C11 H11 117.8 . . ?
C12 C11 H11 117.8 . . ?
C11 C12 C13 117.4(2) . . ?
C11 C12 H12 121.3 . . ?
C13 C12 H12 121.3 . . ?
C14 C13 C12 119.9(2) . . ?
C14 C13 H13 120.0 . . ?
C12 C13 H13 120.0 . . ?
C13 C14 C9 117.9(2) . . ?
C13 C14 H14 121.1 . . ?
C9 C14 H14 121.1 . . ?
O1A C1A H1AA 109.5 . . ?
O1A C1A H1AB 109.5 . . ?
H1AA C1A H1AB 109.5 . . ?
O1A C1A H1AC 109.5 . . ?
H1AA C1A H1AC 109.5 . . ?
H1AB C1A H1AC 109.5 . . ?
C1A O1A H1A 107(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 N1 C2 N3 -0.5(3) . . . . ?
C5 N1 C2 C6 -180.0(2) . . . . ?
N1 C2 N3 C4 0.2(3) . . . . ?
C6 C2 N3 C4 179.6(2) . . . . ?
N1 C2 N3 C31 176.2(2) . . . . ?
C6 C2 N3 C31 -4.3(4) . . . . ?
C2 N3 C4 C5 0.3(3) . . . . ?
C31 N3 C4 C5 -175.8(2) . . . . ?
N3 C4 C5 N1 -0.6(3) . . . . ?
C2 N1 C5 C4 0.7(3) . . . . ?
N3 C2 C6 N7 179.5(2) . . . . ?
N1 C2 C6 N7 -1.1(4) . . . . ?
C2 C6 N7 N8 -179.26(19) . . . . ?
C6 N7 N8 C9 179.2(2) . . . . ?
C6 N7 N8 C81 3.2(3) . . . . ?
N7 N8 C9 N10 179.65(19) . . . . ?
C81 N8 C9 N10 -4.4(3) . . . . ?
N7 N8 C9 C14 -0.2(3) . . . . ?
C81 N8 C9 C14 175.7(2) . . . . ?
C14 C9 N10 C11 -2.9(3) . . . . ?
N8 C9 N10 C11 177.2(2) . . . . ?
C9 N10 C11 C12 0.3(4) . . . . ?
N10 C11 C12 C13 1.7(4) . . . . ?
C11 C12 C13 C14 -1.2(4) . . . . ?
C12 C13 C14 C9 -1.2(4) . . . . ?
N10 C9 C14 C13 3.4(4) . . . . ?
N8 C9 C14 C13 -176.7(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1 Br1 0.91(4) 2.36(4) 3.253(2) 166(4) . yes
O1A H1A Br1 0.92(5) 2.43(5) 3.318(2) 163(5) . yes

_refine_diff_density_max         1.183
_refine_diff_density_min         -1.155
_refine_diff_density_rms         0.140

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_Eu-hydrogen
_database_code_depnum_ccdc_archive 'CCDC 2338932'
loop_
_audit_author_name
_audit_author_address
'Maciej Kubicki'
;Adam Mickiewicz University
Poland
;
_audit_update_record             
;
2024-03-08 deposited with the CCDC.	2024-07-03 downloaded from the CCDC.
;

_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H31 Cl N11 O5 Tb, 2(Cl O4)'
_chemical_formula_sum            'C24 H31 Cl3 N11 O13 Tb'
_chemical_formula_weight         946.87

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Tb Tb -0.1723 4.1537 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.0968(9)
_cell_length_b                   11.9590(8)
_cell_length_c                   17.1192(12)
_cell_angle_alpha                86.084(6)
_cell_angle_beta                 75.282(7)
_cell_angle_gamma                83.710(7)
_cell_volume                     1788.8(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    130(1)
_cell_measurement_reflns_used    1566
_cell_measurement_theta_min      2.9010
_cell_measurement_theta_max      22.8950

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.758
_exptl_crystal_F_000             944
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.07
_exptl_absorpt_coefficient_mu    2.277
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.89399
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?

_diffrn_ambient_temperature      130(1)
_diffrn_radiation_wavelength     0.7107
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_detector_area_resol_mean 16.1544
_diffrn_reflns_number            11546
_diffrn_reflns_av_unetI/netI     0.2422
_diffrn_reflns_av_R_equivalents  0.1416
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.937
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_full        24.998
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.990
_reflns_number_total             6235
_reflns_number_gt                2982
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_molecular_graphics    'Mercury (MacRae et al., 2009)'
_computing_publication_material  'SHELXL (Sheldrick, 2015)'

_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0350P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     .
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6235
_refine_ls_number_parameters     474
_refine_ls_number_restraints     48
_refine_ls_R_factor_all          0.1362
_refine_ls_R_factor_gt           0.0745
_refine_ls_wR_factor_ref         0.1654
_refine_ls_wR_factor_gt          0.1365
_refine_ls_goodness_of_fit_ref   0.877
_refine_ls_restrained_S_all      0.905
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Tb1 Tb 0.37001(7) 0.26113(4) 0.26955(3) 0.0418(2) Uani 1 1 d . . . . .
O1W O 0.2262(9) 0.1533(6) 0.2063(4) 0.054(2) Uani 1 1 d . . . . .
H1W1 H 0.211850 0.197751 0.168236 0.064 Uiso 1 1 d R U . . .
H1W2 H 0.254053 0.090768 0.184949 0.064 Uiso 1 1 d R U . . .
N1A N 0.3178(12) 0.3964(8) 0.1618(6) 0.050(3) Uani 1 1 d . . . . .
C2A C 0.3794(17) 0.3636(11) 0.0844(9) 0.061(4) Uani 1 1 d . . . . .
N3A N 0.3271(14) 0.4478(10) 0.0301(7) 0.065(3) Uani 1 1 d . . . . .
C31A C 0.362(2) 0.4418(13) -0.0548(9) 0.118(7) Uani 1 1 d . . . . .
H31A H 0.302146 0.386769 -0.069222 0.176 Uiso 1 1 calc R U . . .
H31B H 0.471199 0.418446 -0.075224 0.176 Uiso 1 1 calc R U . . .
H31C H 0.337433 0.515878 -0.078953 0.176 Uiso 1 1 calc R U . . .
C4A C 0.2292(16) 0.5261(13) 0.0787(10) 0.075(5) Uani 1 1 d . . . . .
H4A H 0.173191 0.590888 0.061622 0.090 Uiso 1 1 calc R U . . .
C5A C 0.2296(16) 0.4925(11) 0.1536(9) 0.064(4) Uani 1 1 d . . . . .
H5A H 0.171448 0.533200 0.198749 0.077 Uiso 1 1 calc R U . . .
C6A C 0.4854(16) 0.2673(12) 0.0613(8) 0.062(4) Uani 1 1 d . . . . .
H6A H 0.525648 0.245747 0.007043 0.075 Uiso 1 1 calc R U . . .
N7A N 0.5205(13) 0.2121(8) 0.1241(6) 0.054(3) Uani 1 1 d . . . . .
N8A N 0.6158(13) 0.1191(9) 0.1114(6) 0.055(3) Uani 1 1 d . . . . .
C81A C 0.6603(19) 0.0746(12) 0.0278(8) 0.096(6) Uani 1 1 d . . . . .
H81A H 0.570308 0.080480 0.005671 0.144 Uiso 1 1 calc R U . . .
H81B H 0.701362 -0.004450 0.030247 0.144 Uiso 1 1 calc R U . . .
H81C H 0.738181 0.118794 -0.006916 0.144 Uiso 1 1 calc R U . . .
C9A C 0.6669(15) 0.0712(10) 0.1782(9) 0.062(4) Uani 1 1 d . . . . .
N10A N 0.5835(12) 0.1029(8) 0.2536(7) 0.052(3) Uani 1 1 d . . . . .
C11A C 0.6285(15) 0.0519(10) 0.3162(9) 0.064(4) Uani 1 1 d . . . . .
H11A H 0.572515 0.072819 0.368772 0.077 Uiso 1 1 calc R U . . .
C12A C 0.7508(17) -0.0293(10) 0.3103(8) 0.067(5) Uani 1 1 d . . . . .
H12A H 0.779676 -0.063853 0.356490 0.080 Uiso 1 1 calc R U . . .
C13A C 0.829(2) -0.0569(12) 0.2317(10) 0.082(5) Uani 1 1 d . . . . .
H13A H 0.915931 -0.110354 0.224451 0.098 Uiso 1 1 calc R U . . .
C14A C 0.7874(19) -0.0126(13) 0.1668(10) 0.086(5) Uani 1 1 d . . . . .
H14A H 0.838334 -0.037172 0.114348 0.103 Uiso 1 1 calc R U . . .
N1B N 0.5964(11) 0.3689(7) 0.2410(5) 0.041(3) Uani 1 1 d . . . . .
C2B C 0.5783(16) 0.4730(10) 0.2637(7) 0.049(3) Uani 1 1 d . . . . .
N3B N 0.7060(13) 0.5266(9) 0.2385(6) 0.049(3) Uani 1 1 d . . . . .
C31B C 0.7326(16) 0.6403(11) 0.2474(8) 0.074(4) Uani 1 1 d . . . . .
H31D H 0.837445 0.652904 0.218277 0.111 Uiso 1 1 calc R U . . .
H31E H 0.717822 0.653643 0.304854 0.111 Uiso 1 1 calc R U . . .
H31F H 0.660824 0.692111 0.225203 0.111 Uiso 1 1 calc R U . . .
C4B C 0.8136(16) 0.4458(12) 0.1970(7) 0.059(4) Uani 1 1 d . . . . .
H4B H 0.917248 0.455615 0.171334 0.071 Uiso 1 1 calc R U . . .
C5B C 0.7452(15) 0.3517(10) 0.1997(7) 0.052(4) Uani 1 1 d . . . . .
H5B H 0.793381 0.283141 0.176178 0.062 Uiso 1 1 calc R U . . .
C6B C 0.4293(14) 0.5263(9) 0.3075(7) 0.041(3) Uani 1 1 d . . . . .
H6B H 0.415417 0.601700 0.324190 0.049 Uiso 1 1 calc R U . . .
N7B N 0.3199(12) 0.4632(7) 0.3214(6) 0.045(3) Uani 1 1 d . . . . .
N8B N 0.1738(12) 0.5059(8) 0.3630(6) 0.046(3) Uani 1 1 d . . . . .
C81B C 0.1481(16) 0.6208(9) 0.3889(8) 0.078(5) Uani 1 1 d . . . . .
H81D H 0.161057 0.672835 0.341454 0.117 Uiso 1 1 calc R U . . .
H81E H 0.221749 0.632932 0.419771 0.117 Uiso 1 1 calc R U . . .
H81F H 0.044171 0.634222 0.423083 0.117 Uiso 1 1 calc R U . . .
C9B C 0.0588(15) 0.4359(11) 0.3687(7) 0.046(3) Uani 1 1 d . . . . .
N10B N 0.0949(11) 0.3335(7) 0.3393(5) 0.040(2) Uani 1 1 d . . . . .
C11B C -0.0197(16) 0.2654(11) 0.3455(8) 0.059(4) Uani 1 1 d . . . . .
H11B H 0.006716 0.192520 0.324213 0.070 Uiso 1 1 calc R U . . .
C12B C -0.1708(14) 0.2967(12) 0.3807(7) 0.060(4) Uani 1 1 d . . . . .
H12B H -0.247663 0.247290 0.384916 0.072 Uiso 1 1 calc R U . . .
C13B C -0.2040(14) 0.4009(13) 0.4090(8) 0.066(4) Uani 1 1 d . . . . .
H13B H -0.307325 0.424547 0.434158 0.079 Uiso 1 1 calc R U . . .
C14B C -0.0960(15) 0.4751(11) 0.4033(8) 0.059(4) Uani 1 1 d . . . . .
H14B H -0.123644 0.549424 0.421774 0.071 Uiso 1 1 calc R U . . .
Cl1C Cl 0.3784(4) 0.2598(3) 0.4888(2) 0.0659(11) Uani 1 1 d . . . . .
O1C O 0.4347(10) 0.2705(6) 0.4008(5) 0.058(2) Uani 1 1 d . . . . .
O2C O 0.4341(15) 0.1493(9) 0.5132(6) 0.123(4) Uani 1 1 d . U . . .
O3C O 0.4311(14) 0.3445(10) 0.5227(7) 0.121(4) Uani 1 1 d . U . . .
O4C O 0.2149(12) 0.2669(9) 0.5096(6) 0.099(4) Uani 1 1 d . . . . .
N1D N 0.2667(13) 0.0957(9) 0.3617(6) 0.062(3) Uani 1 1 d . . . . .
C2D C 0.2423(15) 0.0170(12) 0.4006(8) 0.055(4) Uani 1 1 d . . . . .
C3D C 0.210(2) -0.0836(12) 0.4548(10) 0.126(8) Uani 1 1 d . . . . .
H3D1 H 0.304353 -0.132937 0.451436 0.188 Uiso 1 1 calc R U . . .
H3D2 H 0.135370 -0.124179 0.438330 0.188 Uiso 1 1 calc R U . . .
H3D3 H 0.167981 -0.060349 0.510484 0.188 Uiso 1 1 calc R U . . .
Cl1E Cl 0.3300(7) -0.1629(4) 0.2094(3) 0.0962(16) Uani 1 1 d . . . . .
O1E O 0.356(2) -0.0655(10) 0.1660(8) 0.180(8) Uani 1 1 d . . . . .
O2E O 0.191(3) -0.1376(17) 0.2528(13) 0.243(9) Uani 1 1 d . U . . .
O3E O 0.3984(17) -0.1837(10) 0.2743(8) 0.139(5) Uani 1 1 d . . . . .
O4E O 0.343(2) -0.2511(13) 0.1684(10) 0.209(7) Uani 1 1 d . U . . .
Cl1F Cl 0.0669(5) 0.2288(4) 0.0206(3) 0.0797(12) Uani 1 1 d . . . . .
O1F O 0.0751(18) 0.2526(13) 0.0974(9) 0.172(6) Uani 1 1 d . U . . .
O2F O 0.031(3) 0.3297(18) -0.0025(12) 0.265(10) Uani 1 1 d . U . . .
O3F O -0.015(3) 0.1506(18) 0.0181(14) 0.280(11) Uani 1 1 d . U . . .
O4F O 0.219(2) 0.2028(12) -0.0201(10) 0.189(7) Uani 1 1 d . U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Tb1 O1W 2.414(8) . ?
Tb1 N1A 2.473(9) . ?
Tb1 O1C 2.475(8) . ?
Tb1 N1B 2.475(10) . ?
Tb1 N10A 2.535(9) . ?
Tb1 N1D 2.552(12) . ?
Tb1 N10B 2.566(9) . ?
Tb1 N7B 2.584(8) . ?
Tb1 N7A 2.590(10) . ?
O1W H1W1 0.8399 . ?
O1W H1W2 0.8401 . ?
N1A C5A 1.348(13) . ?
N1A C2A 1.367(16) . ?
C2A C6A 1.427(17) . ?
C2A N3A 1.448(14) . ?
N3A C4A 1.382(15) . ?
N3A C31A 1.413(16) . ?
C31A H31A 0.9800 . ?
C31A H31B 0.9800 . ?
C31A H31C 0.9800 . ?
C4A C5A 1.318(17) . ?
C4A H4A 0.9500 . ?
C5A H5A 0.9500 . ?
C6A N7A 1.314(14) . ?
C6A H6A 0.9500 . ?
N7A N8A 1.328(11) . ?
N8A C9A 1.405(15) . ?
N8A C81A 1.502(15) . ?
C81A H81A 0.9800 . ?
C81A H81B 0.9800 . ?
C81A H81C 0.9800 . ?
C9A N10A 1.375(15) . ?
C9A C14A 1.386(16) . ?
N10A C11A 1.329(14) . ?
C11A C12A 1.382(15) . ?
C11A H11A 0.9500 . ?
C12A C13A 1.396(18) . ?
C12A H12A 0.9500 . ?
C13A C14A 1.320(18) . ?
C13A H13A 0.9500 . ?
C14A H14A 0.9500 . ?
N1B C2B 1.310(13) . ?
N1B C5B 1.360(14) . ?
C2B N3B 1.348(16) . ?
C2B C6B 1.472(16) . ?
N3B C4B 1.389(14) . ?
N3B C31B 1.431(14) . ?
C31B H31D 0.9800 . ?
C31B H31E 0.9800 . ?
C31B H31F 0.9800 . ?
C4B C5B 1.337(17) . ?
C4B H4B 0.9500 . ?
C5B H5B 0.9500 . ?
C6B N7B 1.279(14) . ?
C6B H6B 0.9500 . ?
N7B N8B 1.398(12) . ?
N8B C9B 1.390(16) . ?
N8B C81B 1.449(13) . ?
C81B H81D 0.9800 . ?
C81B H81E 0.9800 . ?
C81B H81F 0.9800 . ?
C9B N10B 1.331(13) . ?
C9B C14B 1.422(16) . ?
N10B C11B 1.372(16) . ?
C11B C12B 1.375(16) . ?
C11B H11B 0.9500 . ?
C12B C13B 1.342(16) . ?
C12B H12B 0.9500 . ?
C13B C14B 1.376(18) . ?
C13B H13B 0.9500 . ?
C14B H14B 0.9500 . ?
Cl1C O3C 1.386(11) . ?
Cl1C O4C 1.433(10) . ?
Cl1C O2C 1.436(9) . ?
Cl1C O1C 1.465(8) . ?
N1D C2D 1.124(14) . ?
C2D C3D 1.477(18) . ?
C3D H3D1 0.9800 . ?
C3D H3D2 0.9800 . ?
C3D H3D3 0.9800 . ?
Cl1E O4E 1.284(15) . ?
Cl1E O2E 1.31(2) . ?
Cl1E O1E 1.349(12) . ?
Cl1E O3E 1.400(12) . ?
Cl1F O3F 1.27(2) . ?
Cl1F O2F 1.278(18) . ?
Cl1F O4F 1.390(17) . ?
Cl1F O1F 1.387(14) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1W Tb1 N1A 78.9(3) . . ?
O1W Tb1 O1C 139.8(3) . . ?
N1A Tb1 O1C 136.7(3) . . ?
O1W Tb1 N1B 142.8(3) . . ?
N1A Tb1 N1B 78.8(3) . . ?
O1C Tb1 N1B 74.2(3) . . ?
O1W Tb1 N10A 90.8(3) . . ?
N1A Tb1 N10A 126.2(3) . . ?
O1C Tb1 N10A 80.9(3) . . ?
N1B Tb1 N10A 79.0(3) . . ?
O1W Tb1 N1D 68.8(3) . . ?
N1A Tb1 N1D 143.2(4) . . ?
O1C Tb1 N1D 71.2(3) . . ?
N1B Tb1 N1D 137.9(3) . . ?
N10A Tb1 N1D 72.6(3) . . ?
O1W Tb1 N10B 78.7(3) . . ?
N1A Tb1 N10B 81.4(3) . . ?
O1C Tb1 N10B 88.0(3) . . ?
N1B Tb1 N10B 126.4(3) . . ?
N10A Tb1 N10B 148.2(3) . . ?
N1D Tb1 N10B 75.7(3) . . ?
O1W Tb1 N7B 132.2(3) . . ?
N1A Tb1 N7B 70.0(3) . . ?
O1C Tb1 N7B 68.0(3) . . ?
N1B Tb1 N7B 64.6(3) . . ?
N10A Tb1 N7B 136.9(3) . . ?
N1D Tb1 N7B 120.6(3) . . ?
N10B Tb1 N7B 61.8(3) . . ?
O1W Tb1 N7A 68.7(3) . . ?
N1A Tb1 N7A 64.8(3) . . ?
O1C Tb1 N7A 135.5(3) . . ?
N1B Tb1 N7A 74.9(3) . . ?
N10A Tb1 N7A 62.3(3) . . ?
N1D Tb1 N7A 115.8(3) . . ?
N10B Tb1 N7A 136.4(3) . . ?
N7B Tb1 N7A 123.7(3) . . ?
Tb1 O1W H1W1 101.5 . . ?
Tb1 O1W H1W2 127.7 . . ?
H1W1 O1W H1W2 104.5 . . ?
C5A N1A C2A 104.4(11) . . ?
C5A N1A Tb1 139.4(9) . . ?
C2A N1A Tb1 115.6(8) . . ?
N1A C2A C6A 125.7(12) . . ?
N1A C2A N3A 108.0(12) . . ?
C6A C2A N3A 126.1(14) . . ?
C4A N3A C31A 128.7(13) . . ?
C4A N3A C2A 106.1(12) . . ?
C31A N3A C2A 124.9(14) . . ?
N3A C31A H31A 109.5 . . ?
N3A C31A H31B 109.5 . . ?
H31A C31A H31B 109.5 . . ?
N3A C31A H31C 109.5 . . ?
H31A C31A H31C 109.5 . . ?
H31B C31A H31C 109.5 . . ?
C5A C4A N3A 105.8(12) . . ?
C5A C4A H4A 127.1 . . ?
N3A C4A H4A 127.1 . . ?
C4A C5A N1A 115.6(13) . . ?
C4A C5A H5A 122.2 . . ?
N1A C5A H5A 122.2 . . ?
N7A C6A C2A 111.8(12) . . ?
N7A C6A H6A 124.1 . . ?
C2A C6A H6A 124.1 . . ?
C6A N7A N8A 118.1(11) . . ?
C6A N7A Tb1 120.6(9) . . ?
N8A N7A Tb1 120.3(8) . . ?
N7A N8A C9A 116.3(10) . . ?
N7A N8A C81A 117.9(11) . . ?
C9A N8A C81A 125.7(11) . . ?
N8A C81A H81A 109.5 . . ?
N8A C81A H81B 109.5 . . ?
H81A C81A H81B 109.5 . . ?
N8A C81A H81C 109.5 . . ?
H81A C81A H81C 109.5 . . ?
H81B C81A H81C 109.5 . . ?
N10A C9A C14A 122.7(14) . . ?
N10A C9A N8A 117.2(10) . . ?
C14A C9A N8A 119.8(13) . . ?
C11A N10A C9A 116.4(11) . . ?
C11A N10A Tb1 122.6(8) . . ?
C9A N10A Tb1 120.9(8) . . ?
N10A C11A C12A 124.7(12) . . ?
N10A C11A H11A 117.6 . . ?
C12A C11A H11A 117.6 . . ?
C11A C12A C13A 115.2(13) . . ?
C11A C12A H12A 122.4 . . ?
C13A C12A H12A 122.4 . . ?
C14A C13A C12A 123.3(15) . . ?
C14A C13A H13A 118.3 . . ?
C12A C13A H13A 118.3 . . ?
C13A C14A C9A 117.5(16) . . ?
C13A C14A H14A 121.3 . . ?
C9A C14A H14A 121.3 . . ?
C2B N1B C5B 105.2(11) . . ?
C2B N1B Tb1 118.5(8) . . ?
C5B N1B Tb1 136.0(8) . . ?
N1B C2B N3B 113.3(11) . . ?
N1B C2B C6B 122.2(13) . . ?
N3B C2B C6B 124.3(11) . . ?
C2B N3B C4B 103.9(10) . . ?
C2B N3B C31B 130.9(11) . . ?
C4B N3B C31B 125.2(12) . . ?
N3B C31B H31D 109.5 . . ?
N3B C31B H31E 109.5 . . ?
H31D C31B H31E 109.5 . . ?
N3B C31B H31F 109.5 . . ?
H31D C31B H31F 109.5 . . ?
H31E C31B H31F 109.5 . . ?
C5B C4B N3B 107.8(12) . . ?
C5B C4B H4B 126.1 . . ?
N3B C4B H4B 126.1 . . ?
C4B C5B N1B 109.8(11) . . ?
C4B C5B H5B 125.1 . . ?
N1B C5B H5B 125.1 . . ?
N7B C6B C2B 114.8(10) . . ?
N7B C6B H6B 122.6 . . ?
C2B C6B H6B 122.6 . . ?
C6B N7B N8B 119.2(10) . . ?
C6B N7B Tb1 119.8(8) . . ?
N8B N7B Tb1 121.0(8) . . ?
C9B N8B N7B 115.5(9) . . ?
C9B N8B C81B 124.4(10) . . ?
N7B N8B C81B 119.7(11) . . ?
N8B C81B H81D 109.5 . . ?
N8B C81B H81E 109.5 . . ?
H81D C81B H81E 109.5 . . ?
N8B C81B H81F 109.5 . . ?
H81D C81B H81F 109.5 . . ?
H81E C81B H81F 109.5 . . ?
N10B C9B N8B 119.3(11) . . ?
N10B C9B C14B 120.6(13) . . ?
N8B C9B C14B 120.1(11) . . ?
C9B N10B C11B 118.6(11) . . ?
C9B N10B Tb1 122.3(8) . . ?
C11B N10B Tb1 119.1(7) . . ?
C12B C11B N10B 123.6(12) . . ?
C12B C11B H11B 118.2 . . ?
N10B C11B H11B 118.2 . . ?
C13B C12B C11B 116.4(14) . . ?
C13B C12B H12B 121.8 . . ?
C11B C12B H12B 121.8 . . ?
C12B C13B C14B 123.4(12) . . ?
C12B C13B H13B 118.3 . . ?
C14B C13B H13B 118.3 . . ?
C13B C14B C9B 117.2(13) . . ?
C13B C14B H14B 121.4 . . ?
C9B C14B H14B 121.4 . . ?
O3C Cl1C O4C 111.5(7) . . ?
O3C Cl1C O2C 112.6(8) . . ?
O4C Cl1C O2C 108.1(8) . . ?
O3C Cl1C O1C 108.4(7) . . ?
O4C Cl1C O1C 109.3(6) . . ?
O2C Cl1C O1C 106.8(6) . . ?
Cl1C O1C Tb1 145.3(6) . . ?
C2D N1D Tb1 170.1(11) . . ?
N1D C2D C3D 177.5(16) . . ?
C2D C3D H3D1 109.5 . . ?
C2D C3D H3D2 109.5 . . ?
H3D1 C3D H3D2 109.5 . . ?
C2D C3D H3D3 109.5 . . ?
H3D1 C3D H3D3 109.5 . . ?
H3D2 C3D H3D3 109.5 . . ?
O4E Cl1E O2E 113.2(15) . . ?
O4E Cl1E O1E 116.0(11) . . ?
O2E Cl1E O1E 100.8(11) . . ?
O4E Cl1E O3E 111.6(9) . . ?
O2E Cl1E O3E 96.7(11) . . ?
O1E Cl1E O3E 116.4(10) . . ?
O3F Cl1F O2F 120.9(15) . . ?
O3F Cl1F O4F 112.1(12) . . ?
O2F Cl1F O4F 105.9(13) . . ?
O3F Cl1F O1F 115.0(13) . . ?
O2F Cl1F O1F 97.0(11) . . ?
O4F Cl1F O1F 103.6(10) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5A N1A C2A C6A 178.0(13) . . . . ?
Tb1 N1A C2A C6A -8.9(17) . . . . ?
C5A N1A C2A N3A 2.1(14) . . . . ?
Tb1 N1A C2A N3A 175.3(7) . . . . ?
N1A C2A N3A C4A -2.7(14) . . . . ?
C6A C2A N3A C4A -178.5(13) . . . . ?
N1A C2A N3A C31A -177.7(13) . . . . ?
C6A C2A N3A C31A 6(2) . . . . ?
C31A N3A C4A C5A 176.9(15) . . . . ?
C2A N3A C4A C5A 2.1(16) . . . . ?
N3A C4A C5A N1A -0.8(19) . . . . ?
C2A N1A C5A C4A -0.9(18) . . . . ?
Tb1 N1A C5A C4A -171.4(11) . . . . ?
N1A C2A C6A N7A -1(2) . . . . ?
N3A C2A C6A N7A 174.4(12) . . . . ?
C2A C6A N7A N8A 178.6(11) . . . . ?
C2A C6A N7A Tb1 10.0(15) . . . . ?
C6A N7A N8A C9A 171.5(12) . . . . ?
Tb1 N7A N8A C9A -19.9(15) . . . . ?
C6A N7A N8A C81A -8.2(18) . . . . ?
Tb1 N7A N8A C81A 160.5(10) . . . . ?
N7A N8A C9A N10A 18.4(18) . . . . ?
C81A N8A C9A N10A -162.0(13) . . . . ?
N7A N8A C9A C14A -167.9(13) . . . . ?
C81A N8A C9A C14A 12(2) . . . . ?
C14A C9A N10A C11A 3(2) . . . . ?
N8A C9A N10A C11A 176.3(12) . . . . ?
C14A C9A N10A Tb1 178.0(11) . . . . ?
N8A C9A N10A Tb1 -8.4(17) . . . . ?
C9A N10A C11A C12A 0(2) . . . . ?
Tb1 N10A C11A C12A -175.4(11) . . . . ?
N10A C11A C12A C13A 0(2) . . . . ?
C11A C12A C13A C14A -2(3) . . . . ?
C12A C13A C14A C9A 5(3) . . . . ?
N10A C9A C14A C13A -5(2) . . . . ?
N8A C9A C14A C13A -178.3(15) . . . . ?
C5B N1B C2B N3B 1.1(14) . . . . ?
Tb1 N1B C2B N3B -174.2(8) . . . . ?
C5B N1B C2B C6B 177.2(11) . . . . ?
Tb1 N1B C2B C6B 1.9(15) . . . . ?
N1B C2B N3B C4B -0.9(15) . . . . ?
C6B C2B N3B C4B -176.9(11) . . . . ?
N1B C2B N3B C31B 177.2(11) . . . . ?
C6B C2B N3B C31B 1(2) . . . . ?
C2B N3B C4B C5B 0.3(14) . . . . ?
C31B N3B C4B C5B -178.0(11) . . . . ?
N3B C4B C5B N1B 0.4(15) . . . . ?
C2B N1B C5B C4B -0.9(14) . . . . ?
Tb1 N1B C5B C4B 173.1(8) . . . . ?
N1B C2B C6B N7B -0.1(18) . . . . ?
N3B C2B C6B N7B 175.6(11) . . . . ?
C2B C6B N7B N8B 179.8(9) . . . . ?
C2B C6B N7B Tb1 -1.7(14) . . . . ?
C6B N7B N8B C9B 174.0(10) . . . . ?
Tb1 N7B N8B C9B -4.5(12) . . . . ?
C6B N7B N8B C81B 0.6(16) . . . . ?
Tb1 N7B N8B C81B -177.9(8) . . . . ?
N7B N8B C9B N10B 3.7(15) . . . . ?
C81B N8B C9B N10B 176.7(10) . . . . ?
N7B N8B C9B C14B -174.4(10) . . . . ?
C81B N8B C9B C14B -1.3(18) . . . . ?
N8B C9B N10B C11B 179.9(11) . . . . ?
C14B C9B N10B C11B -2.1(17) . . . . ?
N8B C9B N10B Tb1 -1.2(14) . . . . ?
C14B C9B N10B Tb1 176.8(8) . . . . ?
C9B N10B C11B C12B -0.2(19) . . . . ?
Tb1 N10B C11B C12B -179.2(10) . . . . ?
N10B C11B C12B C13B 1(2) . . . . ?
C11B C12B C13B C14B 1(2) . . . . ?
C12B C13B C14B C9B -3(2) . . . . ?
N10B C9B C14B C13B 3.5(18) . . . . ?
N8B C9B C14B C13B -178.5(11) . . . . ?
O3C Cl1C O1C Tb1 -139.0(9) . . . . ?
O4C Cl1C O1C Tb1 -17.2(10) . . . . ?
O2C Cl1C O1C Tb1 99.4(10) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O1W H1W1 O1F 0.84 1.98 2.724(17) 146.8 . yes
O1W H1W2 O1E 0.84 2.00 2.807(14) 159.8 . yes

_refine_diff_density_max         1.466
_refine_diff_density_min         -1.213
_refine_diff_density_rms         0.179

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_Lu-azotan
_database_code_depnum_ccdc_archive 'CCDC 2338933'
loop_
_audit_author_name
_audit_author_address
'Maciej Kubicki'
;Adam Mickiewicz University
Poland
;
_audit_update_record             
;
2024-03-08 deposited with the CCDC.	2024-07-03 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H19 Lu N8 O10 S, C2 H3 N'
_chemical_formula_sum            'C15 H22 Lu N9 O10 S'
_chemical_formula_weight         695.44

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Lu Lu -6.6179 4.6937 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z+1/2'

_cell_length_a                   23.9529(11)
_cell_length_b                   11.3128(4)
_cell_length_c                   9.2768(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2513.77(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    6775
_cell_measurement_theta_min      3.6600
_cell_measurement_theta_max      74.2580

_exptl_crystal_description       block
_exptl_crystal_colour            pale-blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.838
_exptl_crystal_F_000             1368
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.07
_exptl_absorpt_coefficient_mu    8.900
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.20659
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.93a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?

_diffrn_ambient_temperature      293(2)
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, Atlas'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Atlas
_diffrn_detector_area_resol_mean 10.5384
_diffrn_reflns_number            9005
_diffrn_reflns_av_unetI/netI     0.0416
_diffrn_reflns_av_R_equivalents  0.0523
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         3.691
_diffrn_reflns_theta_max         74.353
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.881
_diffrn_reflns_point_group_measured_fraction_full 0.907
_reflns_number_total             4510
_reflns_number_gt                4342
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.670
_reflns_Friedel_fraction_max     0.756
_reflns_Friedel_fraction_full    0.800

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlisPro 1.171.43.93a (Rigaku OD, 2023)'
_computing_cell_refinement       'CrysAlisPro 1.171.43.93a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.43.93a (Rigaku OD, 2023)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_molecular_graphics    'Mercury (MacRae et al., 2009)'
_computing_publication_material  'SHELXL (Sheldrick, 2015)'

_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0981P)²+4.5699P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     .
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1577 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.03(3)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         4510
_refine_ls_number_parameters     330
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0547
_refine_ls_R_factor_gt           0.0531
_refine_ls_wR_factor_ref         0.1540
_refine_ls_wR_factor_gt          0.1517
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_restrained_S_all      1.084
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Lu1 Lu 0.35150(2) 0.51120(4) 0.44343(17) 0.0430(2) Uani 1 1 d . . . . .
N1A N 0.2962(5) 0.4523(11) 0.2400(13) 0.059(2) Uani 1 1 d . . . . .
C2A C 0.2428(6) 0.4715(10) 0.2450(16) 0.053(3) Uani 1 1 d . . . . .
N3A N 0.2166(5) 0.4432(10) 0.1188(12) 0.055(2) Uani 1 1 d . . . . .
C31A C 0.1584(7) 0.4534(18) 0.084(2) 0.077(5) Uani 1 1 d . . . . .
H31A H 0.136699 0.410012 0.152831 0.116 Uiso 1 1 calc R U . . .
H31B H 0.151937 0.421830 -0.010880 0.116 Uiso 1 1 calc R U . . .
H31C H 0.147641 0.535104 0.085832 0.116 Uiso 1 1 calc R U . . .
C4A C 0.2566(6) 0.4011(12) 0.0312(15) 0.058(3) Uani 1 1 d . . . . .
H4A H 0.251875 0.372576 -0.061985 0.070 Uiso 1 1 calc R U . . .
C5A C 0.3062(6) 0.4085(12) 0.1069(14) 0.058(3) Uani 1 1 d . . . . .
H5A H 0.341065 0.386739 0.071705 0.070 Uiso 1 1 calc R U . . .
C6A C 0.2144(6) 0.5178(10) 0.3749(16) 0.049(3) Uani 1 1 d . . . . .
H6A H 0.175840 0.524467 0.383287 0.059 Uiso 1 1 calc R U . . .
N7A N 0.2481(4) 0.5473(8) 0.4735(10) 0.048(2) Uani 1 1 d . . . . .
N8A N 0.2291(5) 0.5888(10) 0.6028(14) 0.060(3) Uani 1 1 d . . . . .
C81A C 0.1682(6) 0.5955(16) 0.626(2) 0.076(4) Uani 1 1 d . . . . .
H81A H 0.151326 0.639747 0.549722 0.114 Uiso 1 1 calc R U . . .
H81B H 0.160958 0.634070 0.716728 0.114 Uiso 1 1 calc R U . . .
H81C H 0.152890 0.517161 0.628422 0.114 Uiso 1 1 calc R U . . .
C9A C 0.2688(6) 0.6247(10) 0.7003(13) 0.052(3) Uani 1 1 d . . . . .
N10A N 0.3221(4) 0.6086(10) 0.6640(14) 0.058(2) Uani 1 1 d . . . . .
C11A C 0.3615(6) 0.6466(15) 0.7556(17) 0.061(3) Uani 1 1 d . . . . .
H11A H 0.398717 0.637111 0.729316 0.074 Uiso 1 1 calc R U . . .
C12A C 0.3501(6) 0.6991(14) 0.8870(17) 0.063(4) Uani 1 1 d . . . . .
H12A H 0.378849 0.725074 0.946585 0.076 Uiso 1 1 calc R U . . .
C13A C 0.2952(7) 0.7119(12) 0.9271(19) 0.072(4) Uani 1 1 d . . . . .
H13A H 0.286061 0.744643 1.015965 0.087 Uiso 1 1 calc R U . . .
C14A C 0.2530(6) 0.6749(12) 0.8321(16) 0.059(3) Uani 1 1 d . . . . .
H14A H 0.215566 0.683456 0.856127 0.071 Uiso 1 1 calc R U . . .
N1B N 0.3501(5) 0.3328(12) 0.6601(16) 0.062(3) Uani 1 1 d . . . . .
O1B O 0.3928(4) 0.3951(9) 0.6412(13) 0.065(2) Uani 1 1 d . . . . .
O2B O 0.3096(4) 0.3537(9) 0.5738(13) 0.069(3) Uani 1 1 d . . . . .
O3B O 0.3472(6) 0.2592(16) 0.756(2) 0.106(5) Uani 1 1 d . . . . .
N1C N 0.3618(5) 0.7193(10) 0.2702(11) 0.055(2) Uani 1 1 d . . . . .
O1C O 0.3851(4) 0.6276(8) 0.2228(10) 0.057(2) Uani 1 1 d . . . . .
O2C O 0.3305(4) 0.7090(8) 0.3788(10) 0.059(2) Uani 1 1 d . . . . .
O3C O 0.3684(7) 0.8169(10) 0.2147(15) 0.092(4) Uani 1 1 d . . . . .
N1D N 0.4258(6) 0.2815(11) 0.3458(16) 0.073(3) Uani 1 1 d . . . . .
O1D O 0.4073(6) 0.3800(11) 0.3248(14) 0.085(4) Uani 1 1 d . . . . .
O2D O 0.3973(8) 0.2051(13) 0.405(2) 0.118(5) Uani 1 1 d . . . . .
O3D O 0.4746(10) 0.264(2) 0.314(3) 0.186(13) Uani 1 1 d . . . . .
C1E C 0.5361(9) 0.5142(19) 0.501(3) 0.106(8) Uani 1 1 d . . . . .
H1EA H 0.533994 0.537632 0.600447 0.159 Uiso 1 1 calc R U . . .
H1EB H 0.573098 0.528689 0.465376 0.159 Uiso 1 1 calc R U . . .
H1EC H 0.527677 0.431520 0.492992 0.159 Uiso 1 1 calc R U . . .
O1E O 0.4346(3) 0.5938(9) 0.4896(10) 0.058(2) Uani 1 1 d . . . . .
S1E S 0.48842(13) 0.5950(4) 0.4011(4) 0.0631(8) Uani 1 1 d . . . . .
C2E C 0.5164(8) 0.7366(17) 0.437(3) 0.116(8) Uani 1 1 d . . . . .
H2EA H 0.518208 0.749024 0.538764 0.173 Uiso 1 1 calc R U . . .
H2EB H 0.492995 0.795785 0.393618 0.173 Uiso 1 1 calc R U . . .
H2EC H 0.553275 0.741862 0.396348 0.173 Uiso 1 1 calc R U . . .
C1F C 0.5030(14) 0.082(4) 0.595(4) 0.19(2) Uani 1 1 d D . . . .
H1FA H 0.469538 0.119892 0.562038 0.290 Uiso 1 1 calc R U . . .
H1FB H 0.523406 0.134551 0.656334 0.290 Uiso 1 1 calc R U . . .
H1FC H 0.493491 0.011522 0.647288 0.290 Uiso 1 1 calc R U . . .
C2F C 0.5391(9) 0.049(3) 0.465(4) 0.117(9) Uani 1 1 d D . . . .
N3F N 0.5684(12) 0.018(2) 0.391(3) 0.120(9) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Lu1 O1E 2.240(8) . ?
Lu1 O1D 2.280(10) . ?
Lu1 O2C 2.370(8) . ?
Lu1 O2B 2.376(10) . ?
Lu1 N1A 2.400(12) . ?
Lu1 N10A 2.428(13) . ?
Lu1 O1B 2.463(10) . ?
Lu1 N7A 2.525(10) . ?
Lu1 O1C 2.563(10) . ?
Lu1 N1B 2.849(13) . ?
Lu1 N1C 2.862(11) . ?
N1A C2A 1.299(18) . ?
N1A C5A 1.352(19) . ?
C2A N3A 1.365(17) . ?
C2A C6A 1.48(2) . ?
N3A C4A 1.343(18) . ?
N3A C31A 1.437(18) . ?
C31A H31A 0.9600 . ?
C31A H31B 0.9600 . ?
C31A H31C 0.9600 . ?
C4A C5A 1.382(19) . ?
C4A H4A 0.9300 . ?
C5A H5A 0.9300 . ?
C6A N7A 1.265(16) . ?
C6A H6A 0.9300 . ?
N7A N8A 1.366(15) . ?
N8A C9A 1.375(18) . ?
N8A C81A 1.475(18) . ?
C81A H81A 0.9600 . ?
C81A H81B 0.9600 . ?
C81A H81C 0.9600 . ?
C9A N10A 1.333(17) . ?
C9A C14A 1.400(19) . ?
N10A C11A 1.34(2) . ?
C11A C12A 1.38(2) . ?
C11A H11A 0.9300 . ?
C12A C13A 1.38(2) . ?
C12A H12A 0.9300 . ?
C13A C14A 1.40(2) . ?
C13A H13A 0.9300 . ?
C14A H14A 0.9300 . ?
N1B O3B 1.220(19) . ?
N1B O1B 1.255(15) . ?
N1B O2B 1.279(15) . ?
N1C O3C 1.228(16) . ?
N1C O1C 1.258(15) . ?
N1C O2C 1.261(15) . ?
N1D O1D 1.216(16) . ?
N1D O3D 1.22(2) . ?
N1D O2D 1.23(2) . ?
C1E S1E 1.73(2) . ?
C1E H1EA 0.9600 . ?
C1E H1EB 0.9600 . ?
C1E H1EC 0.9600 . ?
O1E S1E 1.528(9) . ?
S1E C2E 1.767(18) . ?
C2E H2EA 0.9600 . ?
C2E H2EB 0.9600 . ?
C2E H2EC 0.9600 . ?
C1F C2F 1.529(13) . ?
C1F H1FA 0.9600 . ?
C1F H1FB 0.9600 . ?
C1F H1FC 0.9600 . ?
C2F N3F 1.04(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1E Lu1 O1D 81.0(5) . . ?
O1E Lu1 O2C 81.0(4) . . ?
O1D Lu1 O2C 128.1(4) . . ?
O1E Lu1 O2B 126.2(3) . . ?
O1D Lu1 O2B 90.3(5) . . ?
O2C Lu1 O2B 138.3(4) . . ?
O1E Lu1 N1A 139.2(4) . . ?
O1D Lu1 N1A 76.3(5) . . ?
O2C Lu1 N1A 86.9(4) . . ?
O2B Lu1 N1A 87.7(4) . . ?
O1E Lu1 N10A 84.7(4) . . ?
O1D Lu1 N10A 150.7(4) . . ?
O2C Lu1 N10A 73.9(3) . . ?
O2B Lu1 N10A 77.8(4) . . ?
N1A Lu1 N10A 128.9(4) . . ?
O1E Lu1 O1B 73.9(3) . . ?
O1D Lu1 O1B 77.1(4) . . ?
O2C Lu1 O1B 141.0(4) . . ?
O2B Lu1 O1B 52.4(3) . . ?
N1A Lu1 O1B 131.2(4) . . ?
N10A Lu1 O1B 74.4(4) . . ?
O1E Lu1 N7A 141.5(3) . . ?
O1D Lu1 N7A 137.2(4) . . ?
O2C Lu1 N7A 70.6(3) . . ?
O2B Lu1 N7A 69.6(3) . . ?
N1A Lu1 N7A 65.8(4) . . ?
N10A Lu1 N7A 63.2(3) . . ?
O1B Lu1 N7A 113.4(3) . . ?
O1E Lu1 O1C 70.1(3) . . ?
O1D Lu1 O1C 76.4(4) . . ?
O2C Lu1 O1C 51.7(3) . . ?
O2B Lu1 O1C 157.6(4) . . ?
N1A Lu1 O1C 71.8(4) . . ?
N10A Lu1 O1C 122.1(3) . . ?
O1B Lu1 O1C 137.9(3) . . ?
N7A Lu1 O1C 108.2(3) . . ?
O1E Lu1 N1B 99.9(3) . . ?
O1D Lu1 N1B 83.5(4) . . ?
O2C Lu1 N1B 147.6(4) . . ?
O2B Lu1 N1B 26.4(3) . . ?
N1A Lu1 N1B 110.6(4) . . ?
N10A Lu1 N1B 73.9(4) . . ?
O1B Lu1 N1B 26.0(3) . . ?
N7A Lu1 N1B 91.4(3) . . ?
O1C Lu1 N1B 158.6(3) . . ?
O1E Lu1 N1C 71.8(3) . . ?
O1D Lu1 N1C 102.4(4) . . ?
O2C Lu1 N1C 25.8(3) . . ?
O2B Lu1 N1C 160.0(3) . . ?
N1A Lu1 N1C 80.5(4) . . ?
N10A Lu1 N1C 97.2(4) . . ?
O1B Lu1 N1C 145.3(3) . . ?
N7A Lu1 N1C 90.8(3) . . ?
O1C Lu1 N1C 26.1(3) . . ?
N1B Lu1 N1C 168.6(4) . . ?
C2A N1A C5A 105.6(12) . . ?
C2A N1A Lu1 118.0(10) . . ?
C5A N1A Lu1 136.2(10) . . ?
N1A C2A N3A 112.5(13) . . ?
N1A C2A C6A 122.7(12) . . ?
N3A C2A C6A 124.8(12) . . ?
C4A N3A C2A 106.0(11) . . ?
C4A N3A C31A 125.7(13) . . ?
C2A N3A C31A 128.3(13) . . ?
N3A C31A H31A 109.5 . . ?
N3A C31A H31B 109.5 . . ?
H31A C31A H31B 109.5 . . ?
N3A C31A H31C 109.5 . . ?
H31A C31A H31C 109.5 . . ?
H31B C31A H31C 109.5 . . ?
N3A C4A C5A 106.5(12) . . ?
N3A C4A H4A 126.7 . . ?
C5A C4A H4A 126.7 . . ?
N1A C5A C4A 109.5(13) . . ?
N1A C5A H5A 125.3 . . ?
C4A C5A H5A 125.3 . . ?
N7A C6A C2A 112.9(12) . . ?
N7A C6A H6A 123.5 . . ?
C2A C6A H6A 123.5 . . ?
C6A N7A N8A 120.8(11) . . ?
C6A N7A Lu1 120.3(9) . . ?
N8A N7A Lu1 118.7(7) . . ?
N7A N8A C9A 116.6(10) . . ?
N7A N8A C81A 118.6(12) . . ?
C9A N8A C81A 124.8(13) . . ?
N8A C81A H81A 109.5 . . ?
N8A C81A H81B 109.5 . . ?
H81A C81A H81B 109.5 . . ?
N8A C81A H81C 109.5 . . ?
H81A C81A H81C 109.5 . . ?
H81B C81A H81C 109.5 . . ?
N10A C9A N8A 117.2(12) . . ?
N10A C9A C14A 122.3(13) . . ?
N8A C9A C14A 120.5(12) . . ?
C11A N10A C9A 118.0(13) . . ?
C11A N10A Lu1 118.5(9) . . ?
C9A N10A Lu1 123.5(9) . . ?
N10A C11A C12A 123.9(14) . . ?
N10A C11A H11A 118.0 . . ?
C12A C11A H11A 118.0 . . ?
C13A C12A C11A 118.2(14) . . ?
C13A C12A H12A 120.9 . . ?
C11A C12A H12A 120.9 . . ?
C12A C13A C14A 119.1(16) . . ?
C12A C13A H13A 120.4 . . ?
C14A C13A H13A 120.4 . . ?
C9A C14A C13A 118.4(14) . . ?
C9A C14A H14A 120.8 . . ?
C13A C14A H14A 120.8 . . ?
O3B N1B O1B 122.1(14) . . ?
O3B N1B O2B 122.7(13) . . ?
O1B N1B O2B 115.2(12) . . ?
O3B N1B Lu1 176.8(13) . . ?
O1B N1B Lu1 59.5(7) . . ?
O2B N1B Lu1 55.7(6) . . ?
N1B O1B Lu1 94.4(8) . . ?
N1B O2B Lu1 97.9(7) . . ?
O3C N1C O1C 122.5(12) . . ?
O3C N1C O2C 119.7(12) . . ?
O1C N1C O2C 117.8(11) . . ?
O3C N1C Lu1 170.4(10) . . ?
O1C N1C Lu1 63.6(6) . . ?
O2C N1C Lu1 54.8(6) . . ?
N1C O1C Lu1 90.3(7) . . ?
N1C O2C Lu1 99.4(7) . . ?
O1D N1D O3D 117.1(18) . . ?
O1D N1D O2D 120.8(15) . . ?
O3D N1D O2D 121.9(17) . . ?
N1D O1D Lu1 137.2(11) . . ?
S1E C1E H1EA 109.5 . . ?
S1E C1E H1EB 109.5 . . ?
H1EA C1E H1EB 109.5 . . ?
S1E C1E H1EC 109.5 . . ?
H1EA C1E H1EC 109.5 . . ?
H1EB C1E H1EC 109.5 . . ?
S1E O1E Lu1 130.6(5) . . ?
O1E S1E C1E 105.3(9) . . ?
O1E S1E C2E 103.2(9) . . ?
C1E S1E C2E 97.4(12) . . ?
S1E C2E H2EA 109.5 . . ?
S1E C2E H2EB 109.5 . . ?
H2EA C2E H2EB 109.5 . . ?
S1E C2E H2EC 109.5 . . ?
H2EA C2E H2EC 109.5 . . ?
H2EB C2E H2EC 109.5 . . ?
C2F C1F H1FA 109.5 . . ?
C2F C1F H1FB 109.5 . . ?
H1FA C1F H1FB 109.5 . . ?
C2F C1F H1FC 109.5 . . ?
H1FA C1F H1FC 109.5 . . ?
H1FB C1F H1FC 109.5 . . ?
N3F C2F C1F 169(4) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5A N1A C2A N3A -0.7(15) . . . . ?
Lu1 N1A C2A N3A 175.0(8) . . . . ?
C5A N1A C2A C6A 178.8(12) . . . . ?
Lu1 N1A C2A C6A -5.6(16) . . . . ?
N1A C2A N3A C4A 1.5(15) . . . . ?
C6A C2A N3A C4A -177.9(12) . . . . ?
N1A C2A N3A C31A -179.4(15) . . . . ?
C6A C2A N3A C31A 1(2) . . . . ?
C2A N3A C4A C5A -1.6(14) . . . . ?
C31A N3A C4A C5A 179.2(15) . . . . ?
C2A N1A C5A C4A -0.3(15) . . . . ?
Lu1 N1A C5A C4A -174.8(10) . . . . ?
N3A C4A C5A N1A 1.3(16) . . . . ?
N1A C2A C6A N7A 6.6(17) . . . . ?
N3A C2A C6A N7A -174.0(12) . . . . ?
C2A C6A N7A N8A -178.1(10) . . . . ?
C2A C6A N7A Lu1 -4.3(13) . . . . ?
C6A N7A N8A C9A -176.6(11) . . . . ?
Lu1 N7A N8A C9A 9.5(14) . . . . ?
C6A N7A N8A C81A 1.6(18) . . . . ?
Lu1 N7A N8A C81A -172.4(10) . . . . ?
N7A N8A C9A N10A -4.3(16) . . . . ?
C81A N8A C9A N10A 177.7(13) . . . . ?
N7A N8A C9A C14A 176.2(11) . . . . ?
C81A N8A C9A C14A -1.8(19) . . . . ?
N8A C9A N10A C11A 177.9(12) . . . . ?
C14A C9A N10A C11A -2.7(19) . . . . ?
N8A C9A N10A Lu1 -3.3(15) . . . . ?
C14A C9A N10A Lu1 176.1(9) . . . . ?
C9A N10A C11A C12A 1(2) . . . . ?
Lu1 N10A C11A C12A -177.4(12) . . . . ?
N10A C11A C12A C13A 1(3) . . . . ?
C11A C12A C13A C14A -2(2) . . . . ?
N10A C9A C14A C13A 1.6(19) . . . . ?
N8A C9A C14A C13A -179.0(12) . . . . ?
C12A C13A C14A C9A 1(2) . . . . ?
O3B N1B O1B Lu1 -176.8(17) . . . . ?
O2B N1B O1B Lu1 1.9(14) . . . . ?
O3B N1B O2B Lu1 176.7(17) . . . . ?
O1B N1B O2B Lu1 -2.0(15) . . . . ?
O3C N1C O1C Lu1 171.5(13) . . . . ?
O2C N1C O1C Lu1 -8.6(11) . . . . ?
O3C N1C O2C Lu1 -170.7(12) . . . . ?
O1C N1C O2C Lu1 9.4(12) . . . . ?
O3D N1D O1D Lu1 -138(2) . . . . ?
O2D N1D O1D Lu1 38(3) . . . . ?
Lu1 O1E S1E C1E -113.9(11) . . . . ?
Lu1 O1E S1E C2E 144.5(12) . . . . ?

_refine_diff_density_max         2.224
_refine_diff_density_min         -1.796
_refine_diff_density_rms         0.182

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_Tb-perchlorate
_database_code_depnum_ccdc_archive 'CCDC 2338934'
loop_
_audit_author_name
_audit_author_address
'Maciej Kubicki'
;Adam Mickiewicz University
Poland
;
_audit_update_record             
;
2024-03-08 deposited with the CCDC.	2024-07-03 downloaded from the CCDC.
;

_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         
;
C23 H26 Eu F6 N10 O7 S2, C F3 O3 S, C H4 O
;
_chemical_formula_sum            'C25 H30 Eu F9 N10 O11 S3'
_chemical_formula_weight         1065.73

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Eu Eu -0.1578 3.6682 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   13.59487(17)
_cell_length_b                   15.49254(18)
_cell_length_c                   17.9886(3)
_cell_angle_alpha                90
_cell_angle_beta                 92.7582(12)
_cell_angle_gamma                90
_cell_volume                     3784.35(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(1)
_cell_measurement_reflns_used    12674
_cell_measurement_theta_min      3.2410
_cell_measurement_theta_max      27.9880

_exptl_crystal_description       needle
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.871
_exptl_crystal_F_000             2120
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.07
_exptl_absorpt_coefficient_mu    1.936
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.86502
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?

_diffrn_ambient_temperature      100(1)
_diffrn_radiation_wavelength     0.7107
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_detector_area_resol_mean 16.1544
_diffrn_reflns_number            38298
_diffrn_reflns_av_unetI/netI     0.0366
_diffrn_reflns_av_R_equivalents  0.0369
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.863
_diffrn_reflns_theta_max         28.266
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.901
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.901
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.901
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             8448
_reflns_number_gt                7065
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_molecular_graphics    'Mercury (MacRae et al., 2009)'
_computing_publication_material  'SHELXL (Sheldrick, 2015)'

_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0194P)²+2.9237P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     .
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         8448
_refine_ls_number_parameters     538
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0393
_refine_ls_R_factor_gt           0.0269
_refine_ls_wR_factor_ref         0.0553
_refine_ls_wR_factor_gt          0.0517
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.044
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Eu1 Eu 0.26377(2) 0.15627(2) 0.66480(2) 0.01186(4) Uani 1 1 d . . . . .
N1A N 0.35624(16) 0.29412(13) 0.65675(12) 0.0170(5) Uani 1 1 d . . . . .
C2A C 0.32118(19) 0.35091(15) 0.60677(14) 0.0159(5) Uani 1 1 d . . . . .
N3A N 0.38462(16) 0.41684(13) 0.59979(13) 0.0205(5) Uani 1 1 d . . . . .
H3A H 0.376700 0.461154 0.569493 0.025 Uiso 1 1 calc R U . . .
C4A C 0.4632(2) 0.40264(17) 0.64802(16) 0.0228(6) Uani 1 1 d . . . . .
H4A H 0.519606 0.438333 0.655687 0.027 Uiso 1 1 calc R U . . .
C5A C 0.4446(2) 0.32733(16) 0.68284(16) 0.0214(6) Uani 1 1 d . . . . .
H5A H 0.486850 0.301274 0.720010 0.026 Uiso 1 1 calc R U . . .
C6A C 0.22744(19) 0.34273(16) 0.56652(14) 0.0167(5) Uani 1 1 d . . . . .
H6A H 0.201540 0.387100 0.534819 0.020 Uiso 1 1 calc R U . . .
N7A N 0.18086(15) 0.27136(13) 0.57624(11) 0.0138(4) Uani 1 1 d . . . . .
N8A N 0.09224(16) 0.25667(13) 0.54052(12) 0.0163(5) Uani 1 1 d . . . . .
C81A C 0.0487(2) 0.32026(17) 0.48941(15) 0.0234(6) Uani 1 1 d . . . . .
H81A H 0.014178 0.364070 0.517542 0.035 Uiso 1 1 calc R U . . .
H81B H 0.001964 0.291695 0.454295 0.035 Uiso 1 1 calc R U . . .
H81C H 0.100724 0.347866 0.461939 0.035 Uiso 1 1 calc R U . . .
C9A C 0.04530(19) 0.17991(16) 0.55743(14) 0.0152(5) Uani 1 1 d . . . . .
N10A N 0.09732(16) 0.12300(13) 0.59937(11) 0.0147(5) Uani 1 1 d . . . . .
C11A C 0.0538(2) 0.04668(16) 0.61430(14) 0.0180(6) Uani 1 1 d . . . . .
H11A H 0.090670 0.005439 0.643104 0.022 Uiso 1 1 calc R U . . .
C12A C -0.0400(2) 0.02561(18) 0.59032(15) 0.0222(6) Uani 1 1 d . . . . .
H12A H -0.067723 -0.028618 0.602325 0.027 Uiso 1 1 calc R U . . .
C13A C -0.0935(2) 0.08557(18) 0.54801(16) 0.0247(6) Uani 1 1 d . . . . .
H13A H -0.159249 0.073191 0.530975 0.030 Uiso 1 1 calc R U . . .
C14A C -0.0512(2) 0.16278(17) 0.53090(15) 0.0209(6) Uani 1 1 d . . . . .
H14A H -0.086808 0.204177 0.501419 0.025 Uiso 1 1 calc R U . . .
N1B N 0.31417(17) 0.13530(13) 0.53452(12) 0.0184(5) Uani 1 1 d . . . . .
C2B C 0.4088(2) 0.12082(16) 0.52400(15) 0.0202(6) Uani 1 1 d . . . . .
N3B N 0.42276(19) 0.10833(14) 0.45086(13) 0.0263(6) Uani 1 1 d . . . . .
H3B H 0.479500 0.098069 0.431001 0.032 Uiso 1 1 calc R U . . .
C4B C 0.3338(2) 0.11441(17) 0.41340(16) 0.0255(7) Uani 1 1 d . . . . .
H4B H 0.320900 0.108186 0.361306 0.031 Uiso 1 1 calc R U . . .
C5B C 0.2673(2) 0.13116(16) 0.46531(15) 0.0215(6) Uani 1 1 d . . . . .
H5B H 0.198568 0.138852 0.455288 0.026 Uiso 1 1 calc R U . . .
C6B C 0.4825(2) 0.11517(16) 0.58376(16) 0.0217(6) Uani 1 1 d . . . . .
H6B H 0.549984 0.105803 0.574955 0.026 Uiso 1 1 calc R U . . .
N7B N 0.45170(16) 0.12354(13) 0.65003(13) 0.0191(5) Uani 1 1 d . . . . .
N8B N 0.51412(16) 0.11573(14) 0.71023(13) 0.0211(5) Uani 1 1 d . . . . .
C81B C 0.6173(2) 0.0962(2) 0.69917(19) 0.0365(8) Uani 1 1 d . . . . .
H81D H 0.621897 0.042565 0.670638 0.055 Uiso 1 1 calc R U . . .
H81E H 0.652536 0.089316 0.747636 0.055 Uiso 1 1 calc R U . . .
H81F H 0.646866 0.143516 0.671818 0.055 Uiso 1 1 calc R U . . .
C9B C 0.4762(2) 0.13154(15) 0.77933(16) 0.0195(6) Uani 1 1 d . . . . .
N10B N 0.38088(16) 0.15530(13) 0.77952(12) 0.0173(5) Uani 1 1 d . . . . .
C11B C 0.3443(2) 0.17673(16) 0.84511(15) 0.0200(6) Uani 1 1 d . . . . .
H11B H 0.277249 0.193981 0.845498 0.024 Uiso 1 1 calc R U . . .
C12B C 0.3979(2) 0.17511(16) 0.91119(16) 0.0229(6) Uani 1 1 d . . . . .
H12B H 0.369988 0.192843 0.956110 0.028 Uiso 1 1 calc R U . . .
C13B C 0.4947(2) 0.14669(17) 0.91059(17) 0.0272(7) Uani 1 1 d . . . . .
H13B H 0.533308 0.142334 0.955889 0.033 Uiso 1 1 calc R U . . .
C14B C 0.5344(2) 0.12501(17) 0.84493(17) 0.0254(7) Uani 1 1 d . . . . .
H14B H 0.600665 0.105769 0.843966 0.031 Uiso 1 1 calc R U . . .
C1C C 0.0048(2) 0.33745(17) 0.72633(15) 0.0233(6) Uani 1 1 d . . . . .
F1C F 0.01396(13) 0.36550(11) 0.65702(9) 0.0329(4) Uani 1 1 d . . . . .
O1C O 0.16783(13) 0.25444(11) 0.73484(9) 0.0183(4) Uani 1 1 d . . . . .
S1C S 0.12471(5) 0.32580(4) 0.77451(4) 0.01819(14) Uani 1 1 d . . . . .
F2C F -0.05016(13) 0.39432(11) 0.76062(9) 0.0333(4) Uani 1 1 d . . . . .
O2C O 0.17270(16) 0.40685(12) 0.76430(11) 0.0291(5) Uani 1 1 d . . . . .
F3C F -0.04244(12) 0.26268(10) 0.72324(10) 0.0358(4) Uani 1 1 d . . . . .
O3C O 0.10170(15) 0.30473(12) 0.84923(10) 0.0257(5) Uani 1 1 d . . . . .
C1D C 0.2714(2) -0.16298(17) 0.65615(15) 0.0225(6) Uani 1 1 d . . . . .
F1D F 0.18070(12) -0.16289(10) 0.62498(9) 0.0297(4) Uani 1 1 d . . . . .
O1D O 0.28460(13) 0.00134(11) 0.65177(10) 0.0202(4) Uani 1 1 d . . . . .
S1D S 0.34130(5) -0.07080(4) 0.62480(4) 0.02106(15) Uani 1 1 d . . . . .
F2D F 0.26475(14) -0.16303(10) 0.72901(9) 0.0333(4) Uani 1 1 d . . . . .
O2D O 0.33978(16) -0.07926(12) 0.54529(11) 0.0299(5) Uani 1 1 d . . . . .
F3D F 0.31472(13) -0.23607(10) 0.63695(10) 0.0360(4) Uani 1 1 d . . . . .
O3D O 0.43664(14) -0.08078(12) 0.66190(12) 0.0304(5) Uani 1 1 d . . . . .
C1E C 0.0916(2) 0.08492(18) 0.79758(15) 0.0235(6) Uani 1 1 d . . . . .
H1EA H 0.094805 0.139333 0.825367 0.035 Uiso 1 1 calc R U . . .
H1EB H 0.083269 0.036872 0.832145 0.035 Uiso 1 1 calc R U . . .
H1EC H 0.035640 0.086504 0.761169 0.035 Uiso 1 1 calc R U . . .
O1E O 0.18086(13) 0.07330(11) 0.75966(10) 0.0165(4) Uani 1 1 d . . . . .
H1E H 0.217376 0.038094 0.783381 0.020 Uiso 1 1 calc R U . . .
C1F C 0.7364(2) 0.33469(18) 0.57098(17) 0.0279(7) Uani 1 1 d . . . . .
F1F F 0.65520(14) 0.29666(10) 0.59199(11) 0.0411(5) Uani 1 1 d . . . . .
O1F O 0.81593(15) 0.48395(14) 0.54754(11) 0.0336(5) Uani 1 1 d . . . . .
S1F S 0.72389(5) 0.45239(4) 0.57196(4) 0.02135(15) Uani 1 1 d . . . . .
F2F F 0.81029(14) 0.30934(12) 0.61671(10) 0.0422(5) Uani 1 1 d . . . . .
O2F O 0.64058(15) 0.46622(12) 0.52062(11) 0.0275(5) Uani 1 1 d . . . . .
F3F F 0.75401(15) 0.30656(12) 0.50338(10) 0.0441(5) Uani 1 1 d . . . . .
O3F O 0.70478(14) 0.47028(11) 0.64875(10) 0.0231(4) Uani 1 1 d . . . . .
C1G C 0.8528(3) 0.0854(2) 0.8583(2) 0.0528(11) Uani 1 1 d . . . . .
H1GA H 0.836006 0.129793 0.894374 0.079 Uiso 1 1 calc R U . . .
H1GB H 0.876045 0.113157 0.813394 0.079 Uiso 1 1 calc R U . . .
H1GC H 0.904899 0.048267 0.880146 0.079 Uiso 1 1 calc R U . . .
O1G O 0.76891(16) 0.03530(14) 0.83950(13) 0.0399(6) Uani 1 1 d . . . . .
H1G H 0.783104 -0.002172 0.808019 0.048 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Eu1 O1C 2.4000(17) . ?
Eu1 O1D 2.4296(17) . ?
Eu1 O1E 2.4536(17) . ?
Eu1 N1A 2.486(2) . ?
Eu1 N1B 2.494(2) . ?
Eu1 N10B 2.545(2) . ?
Eu1 N10A 2.553(2) . ?
Eu1 N7A 2.610(2) . ?
Eu1 N7B 2.631(2) . ?
N1A C2A 1.330(3) . ?
N1A C5A 1.369(3) . ?
C2A N3A 1.347(3) . ?
C2A C6A 1.441(4) . ?
N3A C4A 1.361(3) . ?
N3A H3A 0.8800 . ?
C4A C5A 1.354(4) . ?
C4A H4A 0.9500 . ?
C5A H5A 0.9500 . ?
C6A N7A 1.290(3) . ?
C6A H6A 0.9500 . ?
N7A N8A 1.357(3) . ?
N8A C9A 1.390(3) . ?
N8A C81A 1.454(3) . ?
C81A H81A 0.9800 . ?
C81A H81B 0.9800 . ?
C81A H81C 0.9800 . ?
C9A N10A 1.340(3) . ?
C9A C14A 1.399(4) . ?
N10A C11A 1.355(3) . ?
C11A C12A 1.366(4) . ?
C11A H11A 0.9500 . ?
C12A C13A 1.385(4) . ?
C12A H12A 0.9500 . ?
C13A C14A 1.369(4) . ?
C13A H13A 0.9500 . ?
C14A H14A 0.9500 . ?
N1B C2B 1.329(3) . ?
N1B C5B 1.373(3) . ?
C2B N3B 1.352(3) . ?
C2B C6B 1.436(4) . ?
N3B C4B 1.359(4) . ?
N3B H3B 0.8800 . ?
C4B C5B 1.357(4) . ?
C4B H4B 0.9500 . ?
C5B H5B 0.9500 . ?
C6B N7B 1.289(3) . ?
C6B H6B 0.9500 . ?
N7B N8B 1.349(3) . ?
N8B C9B 1.390(4) . ?
N8B C81B 1.458(3) . ?
C81B H81D 0.9800 . ?
C81B H81E 0.9800 . ?
C81B H81F 0.9800 . ?
C9B N10B 1.348(3) . ?
C9B C14B 1.392(4) . ?
N10B C11B 1.344(3) . ?
C11B C12B 1.365(4) . ?
C11B H11B 0.9500 . ?
C12B C13B 1.388(4) . ?
C12B H12B 0.9500 . ?
C13B C14B 1.364(4) . ?
C13B H13B 0.9500 . ?
C14B H14B 0.9500 . ?
C1C F3C 1.324(3) . ?
C1C F2C 1.326(3) . ?
C1C F1C 1.332(3) . ?
C1C S1C 1.818(3) . ?
O1C S1C 1.4544(18) . ?
S1C O2C 1.431(2) . ?
S1C O3C 1.4323(19) . ?
C1D F2D 1.318(3) . ?
C1D F3D 1.329(3) . ?
C1D F1D 1.330(3) . ?
C1D S1D 1.820(3) . ?
O1D S1D 1.4541(18) . ?
S1D O2D 1.435(2) . ?
S1D O3D 1.437(2) . ?
C1E O1E 1.432(3) . ?
C1E H1EA 0.9800 . ?
C1E H1EB 0.9800 . ?
C1E H1EC 0.9800 . ?
O1E H1E 0.8400 . ?
C1F F1F 1.322(4) . ?
C1F F3F 1.325(3) . ?
C1F F2F 1.327(3) . ?
C1F S1F 1.831(3) . ?
O1F S1F 1.432(2) . ?
S1F O2F 1.442(2) . ?
S1F O3F 1.4446(19) . ?
C1G O1G 1.408(4) . ?
C1G H1GA 0.9800 . ?
C1G H1GB 0.9800 . ?
C1G H1GC 0.9800 . ?
O1G H1G 0.8400 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1C Eu1 O1D 138.20(6) . . ?
O1C Eu1 O1E 71.78(6) . . ?
O1D Eu1 O1E 66.99(6) . . ?
O1C Eu1 N1A 77.01(7) . . ?
O1D Eu1 N1A 141.40(6) . . ?
O1E Eu1 N1A 137.83(6) . . ?
O1C Eu1 N1B 139.16(6) . . ?
O1D Eu1 N1B 75.06(6) . . ?
O1E Eu1 N1B 137.85(6) . . ?
N1A Eu1 N1B 83.95(7) . . ?
O1C Eu1 N10B 84.99(6) . . ?
O1D Eu1 N10B 90.06(6) . . ?
O1E Eu1 N10B 73.94(6) . . ?
N1A Eu1 N10B 75.76(7) . . ?
N1B Eu1 N10B 124.87(7) . . ?
O1C Eu1 N10A 82.99(6) . . ?
O1D Eu1 N10A 82.00(6) . . ?
O1E Eu1 N10A 77.77(6) . . ?
N1A Eu1 N10A 125.89(7) . . ?
N1B Eu1 N10A 79.51(7) . . ?
N10B Eu1 N10A 151.49(7) . . ?
O1C Eu1 N7A 70.00(6) . . ?
O1D Eu1 N7A 131.67(6) . . ?
O1E Eu1 N7A 125.66(6) . . ?
N1A Eu1 N7A 65.32(7) . . ?
N1B Eu1 N7A 69.25(7) . . ?
N10B Eu1 N7A 137.20(6) . . ?
N10A Eu1 N7A 60.62(6) . . ?
O1C Eu1 N7B 136.90(7) . . ?
O1D Eu1 N7B 71.43(6) . . ?
O1E Eu1 N7B 116.75(6) . . ?
N1A Eu1 N7B 70.33(7) . . ?
N1B Eu1 N7B 64.41(7) . . ?
N10B Eu1 N7B 60.54(7) . . ?
N10A Eu1 N7B 139.31(7) . . ?
N7A Eu1 N7B 117.58(7) . . ?
C2A N1A C5A 105.3(2) . . ?
C2A N1A Eu1 116.23(17) . . ?
C5A N1A Eu1 137.80(17) . . ?
N1A C2A N3A 110.8(2) . . ?
N1A C2A C6A 124.1(2) . . ?
N3A C2A C6A 125.1(2) . . ?
C2A N3A C4A 107.7(2) . . ?
C2A N3A H3A 126.1 . . ?
C4A N3A H3A 126.1 . . ?
C5A C4A N3A 106.0(2) . . ?
C5A C4A H4A 127.0 . . ?
N3A C4A H4A 127.0 . . ?
C4A C5A N1A 110.2(2) . . ?
C4A C5A H5A 124.9 . . ?
N1A C5A H5A 124.9 . . ?
N7A C6A C2A 115.8(2) . . ?
N7A C6A H6A 122.1 . . ?
C2A C6A H6A 122.1 . . ?
C6A N7A N8A 120.7(2) . . ?
C6A N7A Eu1 117.88(17) . . ?
N8A N7A Eu1 121.45(14) . . ?
N7A N8A C9A 116.5(2) . . ?
N7A N8A C81A 120.7(2) . . ?
C9A N8A C81A 122.8(2) . . ?
N8A C81A H81A 109.5 . . ?
N8A C81A H81B 109.5 . . ?
H81A C81A H81B 109.5 . . ?
N8A C81A H81C 109.5 . . ?
H81A C81A H81C 109.5 . . ?
H81B C81A H81C 109.5 . . ?
N10A C9A N8A 116.8(2) . . ?
N10A C9A C14A 121.9(2) . . ?
N8A C9A C14A 121.3(2) . . ?
C9A N10A C11A 117.5(2) . . ?
C9A N10A Eu1 123.98(17) . . ?
C11A N10A Eu1 118.07(16) . . ?
N10A C11A C12A 123.8(2) . . ?
N10A C11A H11A 118.1 . . ?
C12A C11A H11A 118.1 . . ?
C11A C12A C13A 118.1(3) . . ?
C11A C12A H12A 120.9 . . ?
C13A C12A H12A 120.9 . . ?
C14A C13A C12A 119.6(3) . . ?
C14A C13A H13A 120.2 . . ?
C12A C13A H13A 120.2 . . ?
C13A C14A C9A 119.1(3) . . ?
C13A C14A H14A 120.4 . . ?
C9A C14A H14A 120.4 . . ?
C2B N1B C5B 105.9(2) . . ?
C2B N1B Eu1 117.87(18) . . ?
C5B N1B Eu1 136.18(18) . . ?
N1B C2B N3B 110.2(3) . . ?
N1B C2B C6B 123.3(2) . . ?
N3B C2B C6B 126.5(3) . . ?
C2B N3B C4B 108.0(2) . . ?
C2B N3B H3B 126.0 . . ?
C4B N3B H3B 126.0 . . ?
C5B C4B N3B 106.2(3) . . ?
C5B C4B H4B 126.9 . . ?
N3B C4B H4B 126.9 . . ?
C4B C5B N1B 109.7(3) . . ?
C4B C5B H5B 125.2 . . ?
N1B C5B H5B 125.2 . . ?
N7B C6B C2B 116.1(2) . . ?
N7B C6B H6B 121.9 . . ?
C2B C6B H6B 121.9 . . ?
C6B N7B N8B 120.9(2) . . ?
C6B N7B Eu1 118.23(19) . . ?
N8B N7B Eu1 120.85(16) . . ?
N7B N8B C9B 117.2(2) . . ?
N7B N8B C81B 118.8(2) . . ?
C9B N8B C81B 124.0(2) . . ?
N8B C81B H81D 109.5 . . ?
N8B C81B H81E 109.5 . . ?
H81D C81B H81E 109.5 . . ?
N8B C81B H81F 109.5 . . ?
H81D C81B H81F 109.5 . . ?
H81E C81B H81F 109.5 . . ?
N10B C9B N8B 116.6(2) . . ?
N10B C9B C14B 121.7(3) . . ?
N8B C9B C14B 121.7(3) . . ?
C11B N10B C9B 117.8(2) . . ?
C11B N10B Eu1 117.83(17) . . ?
C9B N10B Eu1 124.31(18) . . ?
N10B C11B C12B 123.7(3) . . ?
N10B C11B H11B 118.1 . . ?
C12B C11B H11B 118.1 . . ?
C11B C12B C13B 117.8(3) . . ?
C11B C12B H12B 121.1 . . ?
C13B C12B H12B 121.1 . . ?
C14B C13B C12B 120.0(3) . . ?
C14B C13B H13B 120.0 . . ?
C12B C13B H13B 120.0 . . ?
C13B C14B C9B 119.0(3) . . ?
C13B C14B H14B 120.5 . . ?
C9B C14B H14B 120.5 . . ?
F3C C1C F2C 108.6(2) . . ?
F3C C1C F1C 108.3(2) . . ?
F2C C1C F1C 107.4(2) . . ?
F3C C1C S1C 110.79(18) . . ?
F2C C1C S1C 110.87(19) . . ?
F1C C1C S1C 110.9(2) . . ?
S1C O1C Eu1 168.91(12) . . ?
O2C S1C O3C 116.23(12) . . ?
O2C S1C O1C 114.02(12) . . ?
O3C S1C O1C 113.49(11) . . ?
O2C S1C C1C 104.81(13) . . ?
O3C S1C C1C 103.80(13) . . ?
O1C S1C C1C 102.42(12) . . ?
F2D C1D F3D 108.1(2) . . ?
F2D C1D F1D 108.2(2) . . ?
F3D C1D F1D 107.7(2) . . ?
F2D C1D S1D 111.75(18) . . ?
F3D C1D S1D 110.11(19) . . ?
F1D C1D S1D 110.84(18) . . ?
S1D O1D Eu1 149.05(11) . . ?
O2D S1D O3D 114.97(13) . . ?
O2D S1D O1D 114.84(12) . . ?
O3D S1D O1D 114.11(12) . . ?
O2D S1D C1D 104.74(12) . . ?
O3D S1D C1D 104.13(13) . . ?
O1D S1D C1D 101.94(12) . . ?
O1E C1E H1EA 109.5 . . ?
O1E C1E H1EB 109.5 . . ?
H1EA C1E H1EB 109.5 . . ?
O1E C1E H1EC 109.5 . . ?
H1EA C1E H1EC 109.5 . . ?
H1EB C1E H1EC 109.5 . . ?
C1E O1E Eu1 133.93(15) . . ?
C1E O1E H1E 109.5 . . ?
Eu1 O1E H1E 114.4 . . ?
F1F C1F F3F 107.8(2) . . ?
F1F C1F F2F 108.0(2) . . ?
F3F C1F F2F 107.8(2) . . ?
F1F C1F S1F 111.2(2) . . ?
F3F C1F S1F 110.9(2) . . ?
F2F C1F S1F 110.9(2) . . ?
O1F S1F O2F 115.07(12) . . ?
O1F S1F O3F 115.32(12) . . ?
O2F S1F O3F 114.33(12) . . ?
O1F S1F C1F 104.73(14) . . ?
O2F S1F C1F 102.23(12) . . ?
O3F S1F C1F 102.78(13) . . ?
O1G C1G H1GA 109.5 . . ?
O1G C1G H1GB 109.5 . . ?
H1GA C1G H1GB 109.5 . . ?
O1G C1G H1GC 109.5 . . ?
H1GA C1G H1GC 109.5 . . ?
H1GB C1G H1GC 109.5 . . ?
C1G O1G H1G 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5A N1A C2A N3A 1.1(3) . . . . ?
Eu1 N1A C2A N3A -170.95(16) . . . . ?
C5A N1A C2A C6A -178.3(2) . . . . ?
Eu1 N1A C2A C6A 9.7(3) . . . . ?
N1A C2A N3A C4A -0.9(3) . . . . ?
C6A C2A N3A C4A 178.5(2) . . . . ?
C2A N3A C4A C5A 0.3(3) . . . . ?
N3A C4A C5A N1A 0.4(3) . . . . ?
C2A N1A C5A C4A -0.9(3) . . . . ?
Eu1 N1A C5A C4A 168.4(2) . . . . ?
N1A C2A C6A N7A -6.3(4) . . . . ?
N3A C2A C6A N7A 174.4(2) . . . . ?
C2A C6A N7A N8A -179.5(2) . . . . ?
C2A C6A N7A Eu1 -0.4(3) . . . . ?
C6A N7A N8A C9A -176.8(2) . . . . ?
Eu1 N7A N8A C9A 4.1(3) . . . . ?
C6A N7A N8A C81A 1.2(3) . . . . ?
Eu1 N7A N8A C81A -177.85(17) . . . . ?
N7A N8A C9A N10A -8.6(3) . . . . ?
C81A N8A C9A N10A 173.4(2) . . . . ?
N7A N8A C9A C14A 172.2(2) . . . . ?
C81A N8A C9A C14A -5.7(4) . . . . ?
N8A C9A N10A C11A -177.9(2) . . . . ?
C14A C9A N10A C11A 1.3(4) . . . . ?
N8A C9A N10A Eu1 9.6(3) . . . . ?
C14A C9A N10A Eu1 -171.25(18) . . . . ?
C9A N10A C11A C12A -1.3(4) . . . . ?
Eu1 N10A C11A C12A 171.7(2) . . . . ?
N10A C11A C12A C13A 0.3(4) . . . . ?
C11A C12A C13A C14A 0.7(4) . . . . ?
C12A C13A C14A C9A -0.8(4) . . . . ?
N10A C9A C14A C13A -0.3(4) . . . . ?
N8A C9A C14A C13A 178.8(2) . . . . ?
C5B N1B C2B N3B 0.4(3) . . . . ?
Eu1 N1B C2B N3B 178.12(15) . . . . ?
C5B N1B C2B C6B -176.6(2) . . . . ?
Eu1 N1B C2B C6B 1.2(3) . . . . ?
N1B C2B N3B C4B -0.5(3) . . . . ?
C6B C2B N3B C4B 176.4(2) . . . . ?
C2B N3B C4B C5B 0.4(3) . . . . ?
N3B C4B C5B N1B -0.1(3) . . . . ?
C2B N1B C5B C4B -0.1(3) . . . . ?
Eu1 N1B C5B C4B -177.27(18) . . . . ?
N1B C2B C6B N7B 1.2(4) . . . . ?
N3B C2B C6B N7B -175.3(2) . . . . ?
C2B C6B N7B N8B 177.2(2) . . . . ?
C2B C6B N7B Eu1 -2.8(3) . . . . ?
C6B N7B N8B C9B 175.7(2) . . . . ?
Eu1 N7B N8B C9B -4.3(3) . . . . ?
C6B N7B N8B C81B -1.0(4) . . . . ?
Eu1 N7B N8B C81B 179.02(19) . . . . ?
N7B N8B C9B N10B -1.6(3) . . . . ?
C81B N8B C9B N10B 174.9(2) . . . . ?
N7B N8B C9B C14B 179.8(2) . . . . ?
C81B N8B C9B C14B -3.7(4) . . . . ?
N8B C9B N10B C11B -175.5(2) . . . . ?
C14B C9B N10B C11B 3.1(4) . . . . ?
N8B C9B N10B Eu1 7.2(3) . . . . ?
C14B C9B N10B Eu1 -174.22(18) . . . . ?
C9B N10B C11B C12B -0.5(4) . . . . ?
Eu1 N10B C11B C12B 177.01(19) . . . . ?
N10B C11B C12B C13B -2.4(4) . . . . ?
C11B C12B C13B C14B 2.7(4) . . . . ?
C12B C13B C14B C9B -0.3(4) . . . . ?
N10B C9B C14B C13B -2.7(4) . . . . ?
N8B C9B C14B C13B 175.8(2) . . . . ?
Eu1 O1C S1C O2C 9.3(6) . . . . ?
Eu1 O1C S1C O3C -126.9(6) . . . . ?
Eu1 O1C S1C C1C 121.9(6) . . . . ?
F3C C1C S1C O2C 171.79(18) . . . . ?
F2C C1C S1C O2C -67.6(2) . . . . ?
F1C C1C S1C O2C 51.6(2) . . . . ?
F3C C1C S1C O3C -65.8(2) . . . . ?
F2C C1C S1C O3C 54.8(2) . . . . ?
F1C C1C S1C O3C 173.97(18) . . . . ?
F3C C1C S1C O1C 52.5(2) . . . . ?
F2C C1C S1C O1C 173.10(18) . . . . ?
F1C C1C S1C O1C -67.7(2) . . . . ?
Eu1 O1D S1D O2D -68.6(3) . . . . ?
Eu1 O1D S1D O3D 67.2(3) . . . . ?
Eu1 O1D S1D C1D 178.8(2) . . . . ?
F2D C1D S1D O2D -178.77(19) . . . . ?
F3D C1D S1D O2D 61.1(2) . . . . ?
F1D C1D S1D O2D -58.0(2) . . . . ?
F2D C1D S1D O3D 60.1(2) . . . . ?
F3D C1D S1D O3D -60.0(2) . . . . ?
F1D C1D S1D O3D -179.08(18) . . . . ?
F2D C1D S1D O1D -58.8(2) . . . . ?
F3D C1D S1D O1D -178.92(19) . . . . ?
F1D C1D S1D O1D 62.0(2) . . . . ?
F1F C1F S1F O1F -179.45(19) . . . . ?
F3F C1F S1F O1F -59.4(2) . . . . ?
F2F C1F S1F O1F 60.4(2) . . . . ?
F1F C1F S1F O2F -59.1(2) . . . . ?
F3F C1F S1F O2F 60.9(2) . . . . ?
F2F C1F S1F O2F -179.3(2) . . . . ?
F1F C1F S1F O3F 59.7(2) . . . . ?
F3F C1F S1F O3F 179.7(2) . . . . ?
F2F C1F S1F O3F -60.5(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N3A H3A O2F 0.88 1.98 2.832(3) 163.3 3_666 yes
N3B H3B O2D 0.88 2.49 3.257(3) 145.9 3_656 yes
N3B H3B O3D 0.88 2.09 2.885(3) 150.7 3_656 yes
O1E H1E O3F 0.84 1.89 2.726(2) 170.2 2_646 yes
O1G H1G O2C 0.84 2.03 2.867(3) 175.8 2_646 yes

_refine_diff_density_max         0.659
_refine_diff_density_min         -0.565
_refine_diff_density_rms         0.093

