# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_ms001
_database_code_depnum_ccdc_archive 'CCDC 957999'
_audit_update_record             
;
2013-08-28 deposited with the CCDC.
2015-02-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H21 Eu F4 N4 O10'
_chemical_formula_weight         669.34

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'
Eu Eu -0.1578 3.6682 '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'
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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C2 /c'

loop_
_symmetry_equiv_pos_as_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'
'-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                   22.085(3)
_cell_length_b                   11.3940(13)
_cell_length_c                   20.578(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 111.243(11)
_cell_angle_gamma                90.00
_cell_volume                     4826.3(11)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.842
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2640
_exptl_absorpt_coefficient_mu    2.688
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.6081
_exptl_absorpt_correction_T_max  0.7397
_exptl_absorpt_process_details   'X-Red, X-Shape'
_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9149
_diffrn_reflns_av_R_equivalents  0.0316
_diffrn_reflns_av_sigmaI/netI    0.0694
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.68
_diffrn_reflns_theta_max         28.07
_reflns_number_total             5224
_reflns_number_gt                3597
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0344P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    riding
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5224
_refine_ls_number_parameters     335
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0565
_refine_ls_R_factor_gt           0.0329
_refine_ls_wR_factor_ref         0.0752
_refine_ls_wR_factor_gt          0.0706
_refine_ls_goodness_of_fit_ref   0.920
_refine_ls_restrained_S_all      0.920
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Eu1 Eu 0.402407(11) 0.46086(2) 0.696769(11) 0.01790(6) Uani 1 1 d . . .
F3 F 0.4233(2) 0.0763(3) 0.8054(2) 0.0520(11) Uani 1 1 d . . .
F4 F 0.4221(2) -0.1549(3) 0.8034(2) 0.0568(12) Uani 1 1 d . . .
F9 F 0.4991(2) 0.6877(4) 0.58023(16) 0.0513(10) Uani 1 1 d . . .
F10 F 0.54249(18) 0.2885(3) 0.55832(16) 0.0439(9) Uani 1 1 d . . .
O1 O 0.44545(17) 0.2674(4) 0.72713(19) 0.0302(9) Uani 1 1 d . . .
O6 O 0.44544(19) -0.3452(4) 0.7233(2) 0.0341(10) Uani 1 1 d . . .
O7A O 0.50435(16) 0.4630(4) 0.68012(14) 0.0276(7) Uani 1 1 d . . .
O7B O 0.60474(17) 0.4721(5) 0.68493(17) 0.0433(11) Uani 1 1 d . . .
O11 O 0.30853(19) 0.5822(4) 0.6714(2) 0.0380(10) Uani 1 1 d . . .
O14 O 0.3117(2) 0.3372(4) 0.6867(2) 0.0443(11) Uani 1 1 d . . .
O17 O 0.3495(4) -0.0818(9) 0.5955(4) 0.129(4) Uani 1 1 d . . .
O21 O 0.3784(3) 0.3479(5) 0.5861(2) 0.0582(15) Uani 1 1 d . . .
O22 O 0.3548(3) 0.4222(5) 0.4830(2) 0.0686(18) Uani 1 1 d . . .
O23 O 0.3720(2) 0.5342(5) 0.57318(19) 0.0505(12) Uani 1 1 d . . .
N11 N 0.2261(2) 0.6978(5) 0.6089(2) 0.0379(12) Uani 1 1 d . . .
N14 N 0.2531(2) 0.1730(5) 0.6819(2) 0.0361(11) Uani 1 1 d . . .
N17 N 0.3702(3) 0.0533(8) 0.5254(4) 0.072(2) Uani 1 1 d . . .
N20 N 0.3681(2) 0.4349(5) 0.5457(2) 0.0380(14) Uani 1 1 d . . .
C1 C 0.5000 0.2185(7) 0.7500 0.0224(16) Uani 1 2 d S . .
C2 C 0.5000 0.0862(7) 0.7500 0.0226(16) Uani 1 2 d S . .
C3 C 0.4607(3) 0.0207(5) 0.7760(3) 0.0265(13) Uani 1 1 d . . .
C4 C 0.4607(3) -0.0993(6) 0.7760(3) 0.0313(13) Uani 1 1 d . . .
C5 C 0.5000 -0.1640(7) 0.7500 0.0266(18) Uani 1 2 d S . .
C6 C 0.5000 -0.2975(7) 0.7500 0.0269(17) Uani 1 2 d S . .
C7 C 0.5461(2) 0.4735(5) 0.6516(2) 0.0231(11) Uani 1 1 d . . .
C8 C 0.5216(2) 0.4876(5) 0.5730(2) 0.0270(13) Uani 1 1 d . . .
C9 C 0.4997(3) 0.5931(5) 0.5415(2) 0.0290(12) Uani 1 1 d . . .
C10 C 0.5217(3) 0.3933(5) 0.5305(2) 0.0288(12) Uani 1 1 d . . .
C11 C 0.2865(3) 0.6670(6) 0.6315(3) 0.0375(14) Uani 1 1 d . . .
H11 H 0.3151 0.7103 0.6171 0.062(14) Uiso 1 1 calc R . .
C12 C 0.1791(3) 0.6376(8) 0.6303(4) 0.059(2) Uani 1 1 d . . .
H12A H 0.1982 0.5676 0.6552 0.106(8) Uiso 1 1 calc R . .
H12B H 0.1420 0.6173 0.5898 0.106(8) Uiso 1 1 calc R . .
H12C H 0.1657 0.6880 0.6600 0.106(8) Uiso 1 1 calc R . .
C13 C 0.2017(4) 0.7953(7) 0.5595(4) 0.059(2) Uani 1 1 d . . .
H13A H 0.2374 0.8315 0.5509 0.106(8) Uiso 1 1 calc R . .
H13B H 0.1809 0.8521 0.5788 0.106(8) Uiso 1 1 calc R . .
H13C H 0.1710 0.7659 0.5165 0.106(8) Uiso 1 1 calc R . .
C14 C 0.3051(3) 0.2283(6) 0.6827(3) 0.0375(14) Uani 1 1 d . . .
H14 H 0.3394 0.1837 0.6802 0.062(14) Uiso 1 1 calc R . .
C15 C 0.2494(3) 0.0460(7) 0.6792(3) 0.0519(17) Uani 1 1 d . . .
H15A H 0.2893 0.0146 0.6778 0.106(8) Uiso 1 1 calc R . .
H15B H 0.2139 0.0221 0.6383 0.106(8) Uiso 1 1 calc R . .
H15C H 0.2427 0.0172 0.7199 0.106(8) Uiso 1 1 calc R . .
C16 C 0.1969(3) 0.2362(7) 0.6828(4) 0.056(2) Uani 1 1 d . . .
H16A H 0.2061 0.3187 0.6870 0.106(8) Uiso 1 1 calc R . .
H16B H 0.1861 0.2104 0.7217 0.106(8) Uiso 1 1 calc R . .
H16C H 0.1609 0.2214 0.6403 0.106(8) Uiso 1 1 calc R . .
C17 C 0.3860(5) -0.0336(13) 0.5718(5) 0.094(3) Uani 1 1 d . . .
H17 H 0.4288 -0.0597 0.5874 0.062(14) Uiso 1 1 calc R . .
C18 C 0.4185(6) 0.1083(13) 0.5047(8) 0.124(5) Uani 1 1 d . . .
H18A H 0.4280 0.1848 0.5255 0.106(8) Uiso 1 1 calc R . .
H18B H 0.4026 0.1155 0.4549 0.106(8) Uiso 1 1 calc R . .
H18C H 0.4573 0.0615 0.5200 0.106(8) Uiso 1 1 calc R . .
C19 C 0.3054(5) 0.0953(10) 0.4972(6) 0.092(3) Uani 1 1 d . . .
H19A H 0.2865 0.0743 0.4488 0.106(8) Uiso 1 1 calc R . .
H19B H 0.3053 0.1792 0.5017 0.106(8) Uiso 1 1 calc R . .
H19C H 0.2804 0.0610 0.5220 0.106(8) Uiso 1 1 calc R . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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 O11 2.387(4) . ?
Eu1 O6 2.390(4) 1_565 ?
Eu1 O1 2.393(4) . ?
Eu1 O14 2.396(4) . ?
Eu1 O7A 2.397(3) . ?
Eu1 O7B 2.499(3) 2_656 ?
Eu1 O21 2.500(5) . ?
Eu1 O23 2.526(4) . ?
Eu1 O7A 2.623(3) 2_656 ?
Eu1 C7 2.911(4) 2_656 ?
Eu1 N20 2.936(4) . ?
Eu1 Eu1 4.0667(8) 2_656 ?
F3 C3 1.345(6) . ?
F4 C4 1.340(6) . ?
F9 C9 1.344(6) . ?
F10 C10 1.332(6) . ?
O1 C1 1.254(5) . ?
O6 C6 1.253(5) . ?
O6 Eu1 2.390(4) 1_545 ?
O7A C7 1.264(5) . ?
O7A Eu1 2.623(3) 2_656 ?
O7B C7 1.227(5) . ?
O7B Eu1 2.499(3) 2_656 ?
O11 C11 1.247(7) . ?
O14 C14 1.249(8) . ?
O17 C17 1.215(13) . ?
O21 N20 1.260(7) . ?
O22 N20 1.222(5) . ?
O23 N20 1.254(7) . ?
N11 C11 1.293(7) . ?
N11 C12 1.439(8) . ?
N11 C13 1.470(8) . ?
N14 C14 1.303(7) . ?
N14 C16 1.442(9) . ?
N14 C15 1.450(9) . ?
N17 C17 1.330(14) . ?
N17 C19 1.419(11) . ?
N17 C18 1.428(13) . ?
C1 O1 1.254(5) 2_656 ?
C1 C2 1.508(11) . ?
C2 C3 1.390(7) 2_656 ?
C2 C3 1.390(7) . ?
C3 C4 1.368(7) . ?
C4 C5 1.386(7) . ?
C5 C4 1.386(7) 2_656 ?
C5 C6 1.520(11) . ?
C6 O6 1.253(5) 2_656 ?
C7 C8 1.518(6) . ?
C7 Eu1 2.911(4) 2_656 ?
C8 C9 1.368(8) . ?
C8 C10 1.385(8) . ?
C9 C10 1.391(6) 5_666 ?
C10 C9 1.391(6) 5_666 ?
C11 H11 0.9300 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14 0.9300 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17 0.9300 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 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
O11 Eu1 O6 75.90(15) . 1_565 ?
O11 Eu1 O1 145.30(14) . . ?
O6 Eu1 O1 134.85(11) 1_565 . ?
O11 Eu1 O14 71.86(14) . . ?
O6 Eu1 O14 144.54(15) 1_565 . ?
O1 Eu1 O14 73.82(14) . . ?
O11 Eu1 O7A 138.52(14) . . ?
O6 Eu1 O7A 72.94(15) 1_565 . ?
O1 Eu1 O7A 75.04(14) . . ?
O14 Eu1 O7A 142.46(16) . . ?
O11 Eu1 O7B 80.05(14) . 2_656 ?
O6 Eu1 O7B 83.74(16) 1_565 2_656 ?
O1 Eu1 O7B 87.25(15) . 2_656 ?
O14 Eu1 O7B 76.60(16) . 2_656 ?
O7A Eu1 O7B 122.20(10) . 2_656 ?
O11 Eu1 O21 102.61(17) . . ?
O6 Eu1 O21 128.27(15) 1_565 . ?
O1 Eu1 O21 72.33(15) . . ?
O14 Eu1 O21 73.99(17) . . ?
O7A Eu1 O21 76.99(16) . . ?
O7B Eu1 O21 147.82(17) 2_656 . ?
O11 Eu1 O23 72.26(14) . . ?
O6 Eu1 O23 82.08(17) 1_565 . ?
O1 Eu1 O23 120.21(15) . . ?
O14 Eu1 O23 101.46(17) . . ?
O7A Eu1 O23 76.90(13) . . ?
O7B Eu1 O23 151.21(16) 2_656 . ?
O21 Eu1 O23 50.33(18) . . ?
O11 Eu1 O7A 121.45(13) . 2_656 ?
O6 Eu1 O7A 70.30(13) 1_565 2_656 ?
O1 Eu1 O7A 69.98(13) . 2_656 ?
O14 Eu1 O7A 115.35(14) . 2_656 ?
O7A Eu1 O7A 71.86(11) . 2_656 ?
O7B Eu1 O7A 50.45(10) 2_656 2_656 ?
O21 Eu1 O7A 135.87(16) . 2_656 ?
O23 Eu1 O7A 143.00(15) . 2_656 ?
O11 Eu1 C7 100.20(14) . 2_656 ?
O6 Eu1 C7 74.99(15) 1_565 2_656 ?
O1 Eu1 C7 78.57(15) . 2_656 ?
O14 Eu1 C7 96.42(15) . 2_656 ?
O7A Eu1 C7 97.46(11) . 2_656 ?
O7B Eu1 C7 24.75(12) 2_656 2_656 ?
O21 Eu1 C7 150.85(17) . 2_656 ?
O23 Eu1 C7 157.02(19) . 2_656 ?
O7A Eu1 C7 25.73(11) 2_656 2_656 ?
O11 Eu1 N20 87.50(14) . . ?
O6 Eu1 N20 105.27(15) 1_565 . ?
O1 Eu1 N20 96.27(14) . . ?
O14 Eu1 N20 87.86(15) . . ?
O7A Eu1 N20 75.21(12) . . ?
O7B Eu1 N20 162.46(13) 2_656 . ?
O21 Eu1 N20 25.21(15) . . ?
O23 Eu1 N20 25.13(17) . . ?
O7A Eu1 N20 146.58(12) 2_656 . ?
C7 Eu1 N20 172.04(14) 2_656 . ?
O11 Eu1 Eu1 141.73(11) . 2_656 ?
O6 Eu1 Eu1 67.72(9) 1_565 2_656 ?
O1 Eu1 Eu1 67.42(9) . 2_656 ?
O14 Eu1 Eu1 137.43(11) . 2_656 ?
O7A Eu1 Eu1 37.80(7) . 2_656 ?
O7B Eu1 Eu1 84.49(8) 2_656 2_656 ?
O21 Eu1 Eu1 108.91(14) . 2_656 ?
O23 Eu1 Eu1 112.67(11) . 2_656 ?
O7A Eu1 Eu1 34.07(7) 2_656 2_656 ?
C7 Eu1 Eu1 59.75(9) 2_656 2_656 ?
N20 Eu1 Eu1 112.75(10) . 2_656 ?
C1 O1 Eu1 138.1(4) . . ?
C6 O6 Eu1 137.8(4) . 1_545 ?
C7 O7A Eu1 161.3(3) . . ?
C7 O7A Eu1 90.0(2) . 2_656 ?
Eu1 O7A Eu1 108.13(10) . 2_656 ?
C7 O7B Eu1 96.8(3) . 2_656 ?
C11 O11 Eu1 133.9(4) . . ?
C14 O14 Eu1 131.6(4) . . ?
N20 O21 Eu1 97.1(3) . . ?
N20 O23 Eu1 96.0(4) . . ?
C11 N11 C12 121.8(5) . . ?
C11 N11 C13 121.6(6) . . ?
C12 N11 C13 116.6(5) . . ?
C14 N14 C16 121.2(6) . . ?
C14 N14 C15 121.4(6) . . ?
C16 N14 C15 117.5(6) . . ?
C17 N17 C19 120.6(9) . . ?
C17 N17 C18 120.6(10) . . ?
C19 N17 C18 118.8(10) . . ?
O22 N20 O23 122.2(6) . . ?
O22 N20 O21 121.3(6) . . ?
O23 N20 O21 116.5(4) . . ?
O22 N20 Eu1 178.7(5) . . ?
O23 N20 Eu1 58.8(3) . . ?
O21 N20 Eu1 57.7(3) . . ?
O1 C1 O1 127.3(8) 2_656 . ?
O1 C1 C2 116.4(4) 2_656 . ?
O1 C1 C2 116.4(4) . . ?
C3 C2 C3 115.1(7) 2_656 . ?
C3 C2 C1 122.4(4) 2_656 . ?
C3 C2 C1 122.4(4) . . ?
F3 C3 C4 118.1(5) . . ?
F3 C3 C2 119.4(6) . . ?
C4 C3 C2 122.5(6) . . ?
F4 C4 C3 118.2(5) . . ?
F4 C4 C5 119.7(6) . . ?
C3 C4 C5 122.1(6) . . ?
C4 C5 C4 115.7(8) 2_656 . ?
C4 C5 C6 122.1(4) 2_656 . ?
C4 C5 C6 122.1(4) . . ?
O6 C6 O6 128.6(8) . 2_656 ?
O6 C6 C5 115.7(4) . . ?
O6 C6 C5 115.7(4) 2_656 . ?
O7B C7 O7A 122.7(4) . . ?
O7B C7 C8 119.5(4) . . ?
O7A C7 C8 117.8(4) . . ?
O7B C7 Eu1 58.5(2) . 2_656 ?
O7A C7 Eu1 64.3(2) . 2_656 ?
C8 C7 Eu1 176.3(4) . 2_656 ?
C9 C8 C10 117.6(4) . . ?
C9 C8 C7 121.7(5) . . ?
C10 C8 C7 120.7(5) . . ?
F9 C9 C8 120.1(4) . . ?
F9 C9 C10 118.0(5) . 5_666 ?
C8 C9 C10 121.8(5) . 5_666 ?
F10 C10 C8 120.2(4) . . ?
F10 C10 C9 119.3(5) . 5_666 ?
C8 C10 C9 120.6(5) . 5_666 ?
O11 C11 N11 123.5(6) . . ?
O11 C11 H11 118.3 . . ?
N11 C11 H11 118.3 . . ?
N11 C12 H12A 109.5 . . ?
N11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
N11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N11 C13 H13A 109.5 . . ?
N11 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
N11 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O14 C14 N14 124.2(6) . . ?
O14 C14 H14 117.9 . . ?
N14 C14 H14 117.9 . . ?
N14 C15 H15A 109.5 . . ?
N14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
N14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N14 C16 H16A 109.5 . . ?
N14 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
N14 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O17 C17 N17 125.7(11) . . ?
O17 C17 H17 117.1 . . ?
N17 C17 H17 117.1 . . ?
N17 C18 H18A 109.5 . . ?
N17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
N17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
N17 C19 H19A 109.5 . . ?
N17 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
N17 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 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










O11 Eu1 O1 C1 -165.3(3) . . . . ?
O6 Eu1 O1 C1 -18.9(5) 1_565 . . . ?
O14 Eu1 O1 C1 -174.1(4) . . . . ?
O7A Eu1 O1 C1 27.2(4) . . . . ?
O7B Eu1 O1 C1 -97.2(4) 2_656 . . . ?
O21 Eu1 O1 C1 108.0(4) . . . . ?
O23 Eu1 O1 C1 91.9(4) . . . . ?
O7A Eu1 O1 C1 -48.6(4) 2_656 . . . ?
C7 Eu1 O1 C1 -73.8(4) 2_656 . . . ?
N20 Eu1 O1 C1 100.0(4) . . . . ?
Eu1 Eu1 O1 C1 -12.1(3) 2_656 . . . ?
O11 Eu1 O7A C7 -46.9(13) . . . . ?
O6 Eu1 O7A C7 -89.9(13) 1_565 . . . ?
O1 Eu1 O7A C7 122.4(13) . . . . ?
O14 Eu1 O7A C7 87.6(13) . . . . ?
O7B Eu1 O7A C7 -160.7(12) 2_656 . . . ?
O21 Eu1 O7A C7 47.5(13) . . . . ?
O23 Eu1 O7A C7 -4.3(13) . . . . ?
O7A Eu1 O7A C7 -164.2(12) 2_656 . . . ?
C7 Eu1 O7A C7 -161.6(13) 2_656 . . . ?
N20 Eu1 O7A C7 21.6(13) . . . . ?
Eu1 Eu1 O7A C7 -165.3(14) 2_656 . . . ?
O11 Eu1 O7A Eu1 118.40(19) . . . 2_656 ?
O6 Eu1 O7A Eu1 75.43(16) 1_565 . . 2_656 ?
O1 Eu1 O7A Eu1 -72.31(16) . . . 2_656 ?
O14 Eu1 O7A Eu1 -107.1(2) . . . 2_656 ?
O7B Eu1 O7A Eu1 4.6(3) 2_656 . . 2_656 ?
O21 Eu1 O7A Eu1 -147.2(2) . . . 2_656 ?
O23 Eu1 O7A Eu1 161.0(2) . . . 2_656 ?
O7A Eu1 O7A Eu1 1.1(2) 2_656 . . 2_656 ?
C7 Eu1 O7A Eu1 3.7(2) 2_656 . . 2_656 ?
N20 Eu1 O7A Eu1 -173.1(2) . . . 2_656 ?
O6 Eu1 O11 C11 58.1(6) 1_565 . . . ?
O1 Eu1 O11 C11 -145.8(5) . . . . ?
O14 Eu1 O11 C11 -136.9(6) . . . . ?
O7A Eu1 O11 C11 15.9(7) . . . . ?
O7B Eu1 O11 C11 144.1(6) 2_656 . . . ?
O21 Eu1 O11 C11 -68.7(6) . . . . ?
O23 Eu1 O11 C11 -28.0(6) . . . . ?
O7A Eu1 O11 C11 114.0(6) 2_656 . . . ?
C7 Eu1 O11 C11 129.6(6) 2_656 . . . ?
N20 Eu1 O11 C11 -48.3(6) . . . . ?
Eu1 Eu1 O11 C11 76.4(6) 2_656 . . . ?
O11 Eu1 O14 C14 168.5(6) . . . . ?
O6 Eu1 O14 C14 -165.9(5) 1_565 . . . ?
O1 Eu1 O14 C14 -16.7(5) . . . . ?
O7A Eu1 O14 C14 18.3(7) . . . . ?
O7B Eu1 O14 C14 -107.7(6) 2_656 . . . ?
O21 Eu1 O14 C14 59.1(5) . . . . ?
O23 Eu1 O14 C14 101.7(5) . . . . ?
O7A Eu1 O14 C14 -74.6(6) 2_656 . . . ?
C7 Eu1 O14 C14 -92.8(5) 2_656 . . . ?
N20 Eu1 O14 C14 80.4(5) . . . . ?
Eu1 Eu1 O14 C14 -41.6(6) 2_656 . . . ?
O11 Eu1 O21 N20 54.6(4) . . . . ?
O6 Eu1 O21 N20 -27.3(5) 1_565 . . . ?
O1 Eu1 O21 N20 -161.1(4) . . . . ?
O14 Eu1 O21 N20 121.2(4) . . . . ?
O7A Eu1 O21 N20 -82.9(4) . . . . ?
O7B Eu1 O21 N20 145.9(3) 2_656 . . . ?
O23 Eu1 O21 N20 0.8(3) . . . . ?
O7A Eu1 O21 N20 -128.7(4) 2_656 . . . ?
C7 Eu1 O21 N20 -164.8(3) 2_656 . . . ?
Eu1 Eu1 O21 N20 -103.4(4) 2_656 . . . ?
O11 Eu1 O23 N20 -125.0(4) . . . . ?
O6 Eu1 O23 N20 157.3(3) 1_565 . . . ?
O1 Eu1 O23 N20 19.3(4) . . . . ?
O14 Eu1 O23 N20 -58.5(3) . . . . ?
O7A Eu1 O23 N20 83.1(3) . . . . ?
O7B Eu1 O23 N20 -141.5(3) 2_656 . . . ?
O21 Eu1 O23 N20 -0.8(3) . . . . ?
O7A Eu1 O23 N20 115.9(4) 2_656 . . . ?
C7 Eu1 O23 N20 161.1(3) 2_656 . . . ?
Eu1 Eu1 O23 N20 95.5(3) 2_656 . . . ?
Eu1 O23 N20 O22 -179.0(5) . . . . ?
Eu1 O23 N20 O21 1.3(6) . . . . ?
Eu1 O21 N20 O22 179.0(5) . . . . ?
Eu1 O21 N20 O23 -1.4(6) . . . . ?
O11 Eu1 N20 O23 51.3(3) . . . . ?
O6 Eu1 N20 O23 -23.3(4) 1_565 . . . ?
O1 Eu1 N20 O23 -163.3(3) . . . . ?
O14 Eu1 N20 O23 123.2(3) . . . . ?
O7A Eu1 N20 O23 -90.6(3) . . . . ?
O7B Eu1 N20 O23 95.9(6) 2_656 . . . ?
O21 Eu1 N20 O23 178.6(6) . . . . ?
O7A Eu1 N20 O23 -100.6(4) 2_656 . . . ?
Eu1 Eu1 N20 O23 -95.2(3) 2_656 . . . ?
O11 Eu1 N20 O21 -127.3(4) . . . . ?
O6 Eu1 N20 O21 158.1(4) 1_565 . . . ?
O1 Eu1 N20 O21 18.1(4) . . . . ?
O14 Eu1 N20 O21 -55.3(4) . . . . ?
O7A Eu1 N20 O21 90.8(4) . . . . ?
O7B Eu1 N20 O21 -82.7(7) 2_656 . . . ?
O23 Eu1 N20 O21 -178.6(6) . . . . ?
O7A Eu1 N20 O21 80.8(5) 2_656 . . . ?
Eu1 Eu1 N20 O21 86.2(4) 2_656 . . . ?
Eu1 O1 C1 O1 9.1(3) . . . 2_656 ?
Eu1 O1 C1 C2 -170.9(3) . . . . ?
O1 C1 C2 C3 -48.2(3) 2_656 . . 2_656 ?
O1 C1 C2 C3 131.8(3) . . . 2_656 ?
O1 C1 C2 C3 131.8(3) 2_656 . . . ?
O1 C1 C2 C3 -48.2(3) . . . . ?
C3 C2 C3 F3 176.9(6) 2_656 . . . ?
C1 C2 C3 F3 -3.1(6) . . . . ?
C3 C2 C3 C4 0.0(4) 2_656 . . . ?
C1 C2 C3 C4 180.0(4) . . . . ?
F3 C3 C4 F4 1.9(9) . . . . ?
C2 C3 C4 F4 178.8(4) . . . . ?
F3 C3 C4 C5 -176.9(4) . . . . ?
C2 C3 C4 C5 0.0(9) . . . . ?
F4 C4 C5 C4 -178.8(6) . . . 2_656 ?
C3 C4 C5 C4 0.0(4) . . . 2_656 ?
F4 C4 C5 C6 1.2(6) . . . . ?
C3 C4 C5 C6 180.0(4) . . . . ?
Eu1 O6 C6 O6 -3.9(3) 1_545 . . 2_656 ?
Eu1 O6 C6 C5 176.1(3) 1_545 . . . ?
C4 C5 C6 O6 -127.8(3) 2_656 . . . ?
C4 C5 C6 O6 52.2(3) . . . . ?
C4 C5 C6 O6 52.2(3) 2_656 . . 2_656 ?
C4 C5 C6 O6 -127.8(3) . . . 2_656 ?
Eu1 O7B C7 O7A -4.1(7) 2_656 . . . ?
Eu1 O7B C7 C8 176.3(5) 2_656 . . . ?
Eu1 O7A C7 O7B 170.0(9) . . . . ?
Eu1 O7A C7 O7B 3.9(6) 2_656 . . . ?
Eu1 O7A C7 C8 -10.5(16) . . . . ?
Eu1 O7A C7 C8 -176.6(5) 2_656 . . . ?
Eu1 O7A C7 Eu1 166.0(13) . . . 2_656 ?
O7B C7 C8 C9 -100.8(7) . . . . ?
O7A C7 C8 C9 79.7(7) . . . . ?
O7B C7 C8 C10 78.3(8) . . . . ?
O7A C7 C8 C10 -101.3(7) . . . . ?
C10 C8 C9 F9 -179.4(5) . . . . ?
C7 C8 C9 F9 -0.3(8) . . . . ?
C10 C8 C9 C10 -0.3(9) . . . 5_666 ?
C7 C8 C9 C10 178.8(5) . . . 5_666 ?
C9 C8 C10 F10 180.0(5) . . . . ?
C7 C8 C10 F10 0.9(8) . . . . ?
C9 C8 C10 C9 0.3(9) . . . 5_666 ?
C7 C8 C10 C9 -178.8(5) . . . 5_666 ?
Eu1 O11 C11 N11 157.5(5) . . . . ?
C12 N11 C11 O11 2.0(10) . . . . ?
C13 N11 C11 O11 -177.3(6) . . . . ?
Eu1 O14 C14 N14 175.4(4) . . . . ?
C16 N14 C14 O14 2.5(9) . . . . ?
C15 N14 C14 O14 -178.2(6) . . . . ?
C19 N17 C17 O17 -2.2(18) . . . . ?
C18 N17 C17 O17 175.8(12) . . . . ?

_diffrn_measured_fraction_theta_max 0.890
_diffrn_reflns_theta_full        28.07
_diffrn_measured_fraction_theta_full 0.890
_refine_diff_density_max         1.081
_refine_diff_density_min         -1.377
_refine_diff_density_rms         0.134
####################################################################### 
# 
# 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_ms091
_database_code_depnum_ccdc_archive 'CCDC 958000'
_audit_update_record             
;
2013-08-28 deposited with the CCDC.
2015-02-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H21 F4 Gd N4 O10'
_chemical_formula_weight         674.63

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'
F F 0.0171 0.0103 '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'
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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   C2/c

loop_
_symmetry_equiv_pos_as_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'
'-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                   22.118(4)
_cell_length_b                   11.3996(16)
_cell_length_c                   20.570(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 111.147(17)
_cell_angle_gamma                90.00
_cell_volume                     4837.2(15)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       blocks
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.50
_exptl_crystal_size_min          0.30
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.853
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2647
_exptl_absorpt_coefficient_mu    2.831
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.0784
_exptl_absorpt_correction_T_max  0.2793
_exptl_absorpt_process_details   'XRed, XShape'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10905
_diffrn_reflns_av_R_equivalents  0.1515
_diffrn_reflns_av_sigmaI/netI    0.2110
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.46
_diffrn_reflns_theta_max         28.11
_reflns_number_total             4124
_reflns_number_gt                2085
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0556P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    riding
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4124
_refine_ls_number_parameters     335
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1330
_refine_ls_R_factor_gt           0.0637
_refine_ls_wR_factor_ref         0.1444
_refine_ls_wR_factor_gt          0.1248
_refine_ls_goodness_of_fit_ref   0.809
_refine_ls_restrained_S_all      0.809
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Gd1 Gd 0.40307(3) 0.46276(5) 0.69740(3) 0.02410(17) Uani 1 1 d . . .
F3 F 0.4234(6) 0.0781(8) 0.8052(6) 0.065(3) Uani 1 1 d . . .
F4 F 0.4219(5) -0.1530(8) 0.8036(6) 0.066(3) Uani 1 1 d . . .
F9 F 0.4999(6) 0.6901(8) 0.5798(4) 0.066(3) Uani 1 1 d . . .
F10 F 0.5426(5) 0.2892(8) 0.5598(4) 0.060(3) Uani 1 1 d . . .
O1 O 0.4462(5) 0.2690(8) 0.7281(5) 0.041(2) Uani 1 1 d . . .
O6 O 0.4451(5) -0.3426(8) 0.7227(5) 0.043(2) Uani 1 1 d . . .
O7A O 0.5038(4) 0.4641(10) 0.6798(4) 0.034(2) Uani 1 1 d . . .
O7B O 0.6040(5) 0.4739(12) 0.6838(4) 0.059(3) Uani 1 1 d . . .
O11 O 0.3093(5) 0.5830(10) 0.6714(5) 0.048(3) Uani 1 1 d . . .
O14 O 0.3126(5) 0.3392(10) 0.6885(6) 0.048(3) Uani 1 1 d . . .
O17 O 0.3478(11) -0.079(3) 0.5942(12) 0.184(13) Uani 1 1 d . . .
O21 O 0.3768(7) 0.3504(11) 0.5861(5) 0.071(4) Uani 1 1 d . . .
O22 O 0.3538(7) 0.4254(12) 0.4839(5) 0.077(4) Uani 1 1 d . . .
O23 O 0.3731(6) 0.5379(12) 0.5738(4) 0.058(3) Uani 1 1 d . . .
N11 N 0.2265(6) 0.6981(12) 0.6093(6) 0.054(4) Uani 1 1 d . . .
N14 N 0.2542(7) 0.1789(13) 0.6827(6) 0.046(3) Uani 1 1 d . . .
N17 N 0.3708(9) 0.0497(19) 0.5255(9) 0.091(6) Uani 1 1 d . . .
N20 N 0.3672(6) 0.4384(13) 0.5471(5) 0.048(4) Uani 1 1 d . . .
C1 C 0.5000 0.2229(17) 0.7500 0.026(4) Uani 1 2 d S . .
C2 C 0.5000 0.0865(15) 0.7500 0.024(4) Uani 1 2 d S . .
C3 C 0.4611(6) 0.0245(14) 0.7761(7) 0.037(3) Uani 1 1 d . . .
C4 C 0.4608(7) -0.0980(12) 0.7760(7) 0.037(3) Uani 1 1 d . . .
C5 C 0.5000 -0.1592(17) 0.7500 0.033(5) Uani 1 2 d S . .
C6 C 0.5000 -0.2946(18) 0.7500 0.040(5) Uani 1 2 d S . .
C7 C 0.5467(6) 0.4745(14) 0.6524(6) 0.031(3) Uani 1 1 d . . .
C8 C 0.5209(6) 0.4886(11) 0.5726(5) 0.028(3) Uani 1 1 d . . .
C9 C 0.4992(7) 0.5933(13) 0.5397(6) 0.035(3) Uani 1 1 d . . .
C10 C 0.5209(6) 0.3943(12) 0.5308(6) 0.035(3) Uani 1 1 d . . .
C11 C 0.2882(9) 0.6704(17) 0.6332(9) 0.054(4) Uani 1 1 d . . .
H11 H 0.3172 0.7172 0.6215 0.12(5) Uiso 1 1 calc R . .
C12 C 0.1811(9) 0.635(2) 0.6292(10) 0.082(6) Uani 1 1 d . . .
H12A H 0.2030 0.5955 0.6726 0.19(3) Uiso 1 1 calc R . .
H12B H 0.1597 0.5779 0.5940 0.19(3) Uiso 1 1 calc R . .
H12C H 0.1495 0.6879 0.6345 0.19(3) Uiso 1 1 calc R . .
C13 C 0.2021(11) 0.7933(18) 0.5604(11) 0.086(7) Uani 1 1 d . . .
H13A H 0.2378 0.8363 0.5562 0.19(3) Uiso 1 1 calc R . .
H13B H 0.1763 0.8447 0.5768 0.19(3) Uiso 1 1 calc R . .
H13C H 0.1760 0.7622 0.5157 0.19(3) Uiso 1 1 calc R . .
C14 C 0.3061(9) 0.2319(15) 0.6842(9) 0.051(4) Uani 1 1 d . . .
H14 H 0.3403 0.1869 0.6819 0.12(5) Uiso 1 1 calc R . .
C15 C 0.2498(8) 0.0500(15) 0.6791(8) 0.058(4) Uani 1 1 d . . .
H15A H 0.2924 0.0174 0.6904 0.19(3) Uiso 1 1 calc R . .
H15B H 0.2230 0.0266 0.6329 0.19(3) Uiso 1 1 calc R . .
H15C H 0.2312 0.0221 0.7118 0.19(3) Uiso 1 1 calc R . .
C16 C 0.1994(8) 0.2419(18) 0.6840(10) 0.067(5) Uani 1 1 d . . .
H16A H 0.2016 0.3214 0.6696 0.19(3) Uiso 1 1 calc R . .
H16B H 0.1988 0.2413 0.7304 0.19(3) Uiso 1 1 calc R . .
H16C H 0.1606 0.2056 0.6528 0.19(3) Uiso 1 1 calc R . .
C17 C 0.3863(13) -0.031(3) 0.5717(12) 0.122(10) Uani 1 1 d . . .
H17 H 0.4293 -0.0549 0.5896 0.12(5) Uiso 1 1 calc R . .
C18 C 0.4176(16) 0.110(3) 0.5077(17) 0.144(13) Uani 1 1 d . . .
H18A H 0.4139 0.1926 0.5146 0.19(3) Uiso 1 1 calc R . .
H18B H 0.4110 0.0954 0.4597 0.19(3) Uiso 1 1 calc R . .
H18C H 0.4600 0.0834 0.5365 0.19(3) Uiso 1 1 calc R . .
C19 C 0.3050(13) 0.098(2) 0.4988(14) 0.110(9) Uani 1 1 d . . .
H19A H 0.2887 0.0968 0.4488 0.19(3) Uiso 1 1 calc R . .
H19B H 0.3058 0.1778 0.5145 0.19(3) Uiso 1 1 calc R . .
H19C H 0.2773 0.0522 0.5156 0.19(3) Uiso 1 1 calc R . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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 O11 2.381(11) . ?
Gd1 O7A 2.382(9) . ?
Gd1 O6 2.390(10) 1_565 ?
Gd1 O14 2.399(11) . ?
Gd1 O1 2.399(10) . ?
Gd1 O21 2.502(10) . ?
Gd1 O7B 2.507(7) 2_656 ?
Gd1 O23 2.534(9) . ?
Gd1 O7A 2.620(7) 2_656 ?
Gd1 C7 2.885(12) 2_656 ?
Gd1 N20 2.914(10) . ?
Gd1 Gd1 4.0464(15) 2_656 ?
F3 C3 1.336(15) . ?
F4 C4 1.345(15) . ?
F9 C9 1.374(15) . ?
F10 C10 1.346(16) . ?
O1 C1 1.228(12) . ?
O6 C6 1.263(13) . ?
O6 Gd1 2.390(10) 1_545 ?
O7A C7 1.272(14) . ?
O7A Gd1 2.620(7) 2_656 ?
O7B C7 1.197(16) . ?
O7B Gd1 2.507(7) 2_656 ?
O11 C11 1.250(19) . ?
O14 C14 1.23(2) . ?
O17 C17 1.24(3) . ?
O21 N20 1.253(16) . ?
O22 N20 1.234(13) . ?
O23 N20 1.247(17) . ?
N11 C11 1.31(2) . ?
N11 C12 1.41(2) . ?
N11 C13 1.45(2) . ?
N14 C14 1.29(2) . ?
N14 C16 1.42(2) . ?
N14 C15 1.47(2) . ?
N17 C17 1.28(3) . ?
N17 C18 1.40(3) . ?
N17 C19 1.47(3) . ?
C1 O1 1.228(12) 2_656 ?
C1 C2 1.56(2) . ?
C2 C3 1.364(17) 2_656 ?
C2 C3 1.364(17) . ?
C3 C4 1.396(17) . ?
C4 C5 1.363(17) . ?
C5 C4 1.363(17) 2_656 ?
C5 C6 1.54(3) . ?
C6 O6 1.263(13) 2_656 ?
C7 C8 1.540(15) . ?
C7 Gd1 2.885(12) 2_656 ?
C8 C9 1.370(18) . ?
C8 C10 1.376(17) . ?
C9 C10 1.363(16) 5_666 ?
C10 C9 1.363(16) 5_666 ?
C11 H11 0.9300 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14 0.9300 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17 0.9300 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 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
O11 Gd1 O7A 138.5(4) . . ?
O11 Gd1 O6 75.7(4) . 1_565 ?
O7A Gd1 O6 73.5(4) . 1_565 ?
O11 Gd1 O14 71.7(4) . . ?
O7A Gd1 O14 142.4(4) . . ?
O6 Gd1 O14 144.1(4) 1_565 . ?
O11 Gd1 O1 145.2(4) . . ?
O7A Gd1 O1 75.0(4) . . ?
O6 Gd1 O1 135.3(3) 1_565 . ?
O14 Gd1 O1 73.8(4) . . ?
O11 Gd1 O21 101.1(4) . . ?
O7A Gd1 O21 77.6(4) . . ?
O6 Gd1 O21 128.2(4) 1_565 . ?
O14 Gd1 O21 73.6(4) . . ?
O1 Gd1 O21 73.1(4) . . ?
O11 Gd1 O7B 80.5(3) . 2_656 ?
O7A Gd1 O7B 122.5(3) . 2_656 ?
O6 Gd1 O7B 84.1(4) 1_565 2_656 ?
O14 Gd1 O7B 76.2(4) . 2_656 ?
O1 Gd1 O7B 87.0(4) . 2_656 ?
O21 Gd1 O7B 147.4(4) . 2_656 ?
O11 Gd1 O23 71.8(3) . . ?
O7A Gd1 O23 76.5(3) . . ?
O6 Gd1 O23 81.1(4) 1_565 . ?
O14 Gd1 O23 102.3(4) . . ?
O1 Gd1 O23 120.7(3) . . ?
O21 Gd1 O23 50.6(4) . . ?
O7B Gd1 O23 151.0(4) 2_656 . ?
O11 Gd1 O7A 122.1(3) . 2_656 ?
O7A Gd1 O7A 72.1(3) . 2_656 ?
O6 Gd1 O7A 71.1(3) 1_565 2_656 ?
O14 Gd1 O7A 114.9(3) . 2_656 ?
O1 Gd1 O7A 69.6(3) . 2_656 ?
O21 Gd1 O7A 136.6(4) . 2_656 ?
O7B Gd1 O7A 50.5(3) 2_656 2_656 ?
O23 Gd1 O7A 142.7(4) . 2_656 ?
O11 Gd1 C7 100.5(4) . 2_656 ?
O7A Gd1 C7 98.2(3) . 2_656 ?
O6 Gd1 C7 75.8(4) 1_565 2_656 ?
O14 Gd1 C7 95.6(4) . 2_656 ?
O1 Gd1 C7 78.3(4) . 2_656 ?
O21 Gd1 C7 151.2(4) . 2_656 ?
O7B Gd1 C7 24.4(3) 2_656 2_656 ?
O23 Gd1 C7 156.8(5) . 2_656 ?
O7A Gd1 C7 26.1(3) 2_656 2_656 ?
O11 Gd1 N20 86.2(4) . . ?
O7A Gd1 N20 75.6(3) . . ?
O6 Gd1 N20 104.8(3) 1_565 . ?
O14 Gd1 N20 87.9(4) . . ?
O1 Gd1 N20 97.0(4) . . ?
O21 Gd1 N20 25.3(4) . . ?
O7B Gd1 N20 161.7(3) 2_656 . ?
O23 Gd1 N20 25.2(4) . . ?
O7A Gd1 N20 147.3(3) 2_656 . ?
C7 Gd1 N20 173.1(4) 2_656 . ?
O11 Gd1 Gd1 142.1(3) . 2_656 ?
O7A Gd1 Gd1 38.05(17) . 2_656 ?
O6 Gd1 Gd1 68.2(3) 1_565 2_656 ?
O14 Gd1 Gd1 137.2(3) . 2_656 ?
O1 Gd1 Gd1 67.4(2) . 2_656 ?
O21 Gd1 Gd1 109.9(3) . 2_656 ?
O7B Gd1 Gd1 84.6(2) 2_656 2_656 ?
O23 Gd1 Gd1 112.3(3) . 2_656 ?
O7A Gd1 Gd1 34.08(18) 2_656 2_656 ?
C7 Gd1 Gd1 60.2(3) 2_656 2_656 ?
N20 Gd1 Gd1 113.5(2) . 2_656 ?
C1 O1 Gd1 137.0(10) . . ?
C6 O6 Gd1 137.3(11) . 1_545 ?
C7 O7A Gd1 162.8(8) . . ?
C7 O7A Gd1 88.6(7) . 2_656 ?
Gd1 O7A Gd1 107.9(3) . 2_656 ?
C7 O7B Gd1 95.8(7) . 2_656 ?
C11 O11 Gd1 134.2(10) . . ?
C14 O14 Gd1 131.5(11) . . ?
N20 O21 Gd1 96.0(8) . . ?
N20 O23 Gd1 94.7(8) . . ?
C11 N11 C12 121.4(14) . . ?
C11 N11 C13 121.3(16) . . ?
C12 N11 C13 117.3(15) . . ?
C14 N14 C16 121.5(15) . . ?
C14 N14 C15 120.8(15) . . ?
C16 N14 C15 117.7(14) . . ?
C17 N17 C18 122(3) . . ?
C17 N17 C19 121(2) . . ?
C18 N17 C19 116(2) . . ?
O22 N20 O23 121.4(13) . . ?
O22 N20 O21 119.9(14) . . ?
O23 N20 O21 118.7(10) . . ?
O22 N20 Gd1 177.7(11) . . ?
O23 N20 Gd1 60.1(6) . . ?
O21 N20 Gd1 58.6(6) . . ?
O1 C1 O1 129.4(19) 2_656 . ?
O1 C1 C2 115.3(9) 2_656 . ?
O1 C1 C2 115.3(9) . . ?
C3 C2 C3 117.6(17) 2_656 . ?
C3 C2 C1 121.2(9) 2_656 . ?
C3 C2 C1 121.2(9) . . ?
F3 C3 C2 121.5(14) . . ?
F3 C3 C4 117.0(13) . . ?
C2 C3 C4 121.4(13) . . ?
F4 C4 C5 121.4(13) . . ?
F4 C4 C3 118.0(13) . . ?
C5 C4 C3 120.7(13) . . ?
C4 C5 C4 118.3(18) 2_656 . ?
C4 C5 C6 120.8(9) 2_656 . ?
C4 C5 C6 120.8(9) . . ?
O6 C6 O6 128.6(19) 2_656 . ?
O6 C6 C5 115.7(10) 2_656 . ?
O6 C6 C5 115.7(10) . . ?
O7B C7 O7A 125.0(11) . . ?
O7B C7 C8 119.3(10) . . ?
O7A C7 C8 115.7(11) . . ?
O7B C7 Gd1 59.8(6) . 2_656 ?
O7A C7 Gd1 65.2(6) . 2_656 ?
C8 C7 Gd1 176.6(10) . 2_656 ?
C9 C8 C10 116.9(10) . . ?
C9 C8 C7 123.1(11) . . ?
C10 C8 C7 120.0(12) . . ?
C10 C9 C8 122.5(12) 5_666 . ?
C10 C9 F9 119.0(13) 5_666 . ?
C8 C9 F9 118.5(9) . . ?
F10 C10 C9 119.3(12) . 5_666 ?
F10 C10 C8 120.0(10) . . ?
C9 C10 C8 120.6(12) 5_666 . ?
O11 C11 N11 122.0(17) . . ?
O11 C11 H11 119.0 . . ?
N11 C11 H11 119.0 . . ?
N11 C12 H12A 109.5 . . ?
N11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
N11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N11 C13 H13A 109.5 . . ?
N11 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
N11 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O14 C14 N14 123.3(17) . . ?
O14 C14 H14 118.3 . . ?
N14 C14 H14 118.3 . . ?
N14 C15 H15A 109.5 . . ?
N14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
N14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N14 C16 H16A 109.5 . . ?
N14 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
N14 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O17 C17 N17 124(3) . . ?
O17 C17 H17 117.8 . . ?
N17 C17 H17 117.8 . . ?
N17 C18 H18A 109.5 . . ?
N17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
N17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
N17 C19 H19A 109.5 . . ?
N17 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
N17 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 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












O11 Gd1 O1 C1 -166.7(7) . . . . ?
O7A Gd1 O1 C1 26.8(8) . . . . ?
O6 Gd1 O1 C1 -19.5(11) 1_565 . . . ?
O14 Gd1 O1 C1 -174.5(10) . . . . ?
O21 Gd1 O1 C1 108.2(9) . . . . ?
O7B Gd1 O1 C1 -98.0(9) 2_656 . . . ?
O23 Gd1 O1 C1 90.6(9) . . . . ?
O7A Gd1 O1 C1 -49.3(8) 2_656 . . . ?
C7 Gd1 O1 C1 -75.1(9) 2_656 . . . ?
N20 Gd1 O1 C1 99.8(9) . . . . ?
Gd1 Gd1 O1 C1 -12.7(8) 2_656 . . . ?
O11 Gd1 O7A C7 -44(4) . . . . ?
O6 Gd1 O7A C7 -87(4) 1_565 . . . ?
O14 Gd1 O7A C7 90(4) . . . . ?
O1 Gd1 O7A C7 125(4) . . . . ?
O21 Gd1 O7A C7 49(3) . . . . ?
O7B Gd1 O7A C7 -159(3) 2_656 . . . ?
O23 Gd1 O7A C7 -3(3) . . . . ?
O7A Gd1 O7A C7 -162(3) 2_656 . . . ?
C7 Gd1 O7A C7 -160(4) 2_656 . . . ?
N20 Gd1 O7A C7 23(3) . . . . ?
Gd1 Gd1 O7A C7 -163(4) 2_656 . . . ?
O11 Gd1 O7A Gd1 119.3(5) . . . 2_656 ?
O6 Gd1 O7A Gd1 75.6(4) 1_565 . . 2_656 ?
O14 Gd1 O7A Gd1 -107.1(6) . . . 2_656 ?
O1 Gd1 O7A Gd1 -72.3(4) . . . 2_656 ?
O21 Gd1 O7A Gd1 -147.8(5) . . . 2_656 ?
O7B Gd1 O7A Gd1 4.1(6) 2_656 . . 2_656 ?
O23 Gd1 O7A Gd1 160.2(5) . . . 2_656 ?
O7A Gd1 O7A Gd1 0.7(5) 2_656 . . 2_656 ?
C7 Gd1 O7A Gd1 3.2(5) 2_656 . . 2_656 ?
N20 Gd1 O7A Gd1 -173.8(5) . . . 2_656 ?
O7A Gd1 O11 C11 11.4(19) . . . . ?
O6 Gd1 O11 C11 54.4(16) 1_565 . . . ?
O14 Gd1 O11 C11 -140.9(17) . . . . ?
O1 Gd1 O11 C11 -148.8(15) . . . . ?
O21 Gd1 O11 C11 -72.5(17) . . . . ?
O7B Gd1 O11 C11 140.7(17) 2_656 . . . ?
O23 Gd1 O11 C11 -30.7(16) . . . . ?
O7A Gd1 O11 C11 110.7(16) 2_656 . . . ?
C7 Gd1 O11 C11 126.7(17) 2_656 . . . ?
N20 Gd1 O11 C11 -51.9(17) . . . . ?
Gd1 Gd1 O11 C11 72.6(17) 2_656 . . . ?
O11 Gd1 O14 C14 167.0(14) . . . . ?
O7A Gd1 O14 C14 17.3(16) . . . . ?
O6 Gd1 O14 C14 -167.1(12) 1_565 . . . ?
O1 Gd1 O14 C14 -17.7(13) . . . . ?
O21 Gd1 O14 C14 59.0(13) . . . . ?
O7B Gd1 O14 C14 -108.6(14) 2_656 . . . ?
O23 Gd1 O14 C14 101.1(14) . . . . ?
O7A Gd1 O14 C14 -75.3(14) 2_656 . . . ?
C7 Gd1 O14 C14 -93.8(14) 2_656 . . . ?
N20 Gd1 O14 C14 80.3(14) . . . . ?
Gd1 Gd1 O14 C14 -42.8(15) 2_656 . . . ?
O11 Gd1 O21 N20 55.1(10) . . . . ?
O7A Gd1 O21 N20 -82.5(10) . . . . ?
O6 Gd1 O21 N20 -25.4(12) 1_565 . . . ?
O14 Gd1 O21 N20 122.0(10) . . . . ?
O1 Gd1 O21 N20 -160.4(10) . . . . ?
O7B Gd1 O21 N20 144.8(8) 2_656 . . . ?
O23 Gd1 O21 N20 0.1(8) . . . . ?
O7A Gd1 O21 N20 -128.9(9) 2_656 . . . ?
C7 Gd1 O21 N20 -166.9(8) 2_656 . . . ?
Gd1 Gd1 O21 N20 -102.9(9) 2_656 . . . ?
O11 Gd1 O23 N20 -122.3(9) . . . . ?
O7A Gd1 O23 N20 84.9(8) . . . . ?
O6 Gd1 O23 N20 159.9(9) 1_565 . . . ?
O14 Gd1 O23 N20 -56.4(9) . . . . ?
O1 Gd1 O23 N20 21.8(10) . . . . ?
O21 Gd1 O23 N20 -0.1(8) . . . . ?
O7B Gd1 O23 N20 -140.0(9) 2_656 . . . ?
O7A Gd1 O23 N20 118.2(9) 2_656 . . . ?
C7 Gd1 O23 N20 163.9(9) 2_656 . . . ?
Gd1 Gd1 O23 N20 98.0(8) 2_656 . . . ?
Gd1 O23 N20 O22 -177.9(12) . . . . ?
Gd1 O23 N20 O21 0.1(14) . . . . ?
Gd1 O21 N20 O22 177.9(11) . . . . ?
Gd1 O21 N20 O23 -0.1(15) . . . . ?
O11 Gd1 N20 O22 -178(100) . . . . ?
O11 Gd1 N20 O23 53.6(9) . . . . ?
O7A Gd1 N20 O23 -88.7(8) . . . . ?
O6 Gd1 N20 O23 -20.5(9) 1_565 . . . ?
O14 Gd1 N20 O23 125.4(9) . . . . ?
O1 Gd1 N20 O23 -161.2(8) . . . . ?
O21 Gd1 N20 O23 179.9(15) . . . . ?
O7B Gd1 N20 O23 96.8(15) 2_656 . . . ?
O7A Gd1 N20 O23 -98.5(10) 2_656 . . . ?
Gd1 Gd1 N20 O23 -92.9(8) 2_656 . . . ?
O11 Gd1 N20 O21 -126.3(10) . . . . ?
O7A Gd1 N20 O21 91.4(10) . . . . ?
O6 Gd1 N20 O21 159.6(10) 1_565 . . . ?
O14 Gd1 N20 O21 -54.5(10) . . . . ?
O1 Gd1 N20 O21 18.9(10) . . . . ?
O7B Gd1 N20 O21 -83.1(17) 2_656 . . . ?
O23 Gd1 N20 O21 -179.9(15) . . . . ?
O7A Gd1 N20 O21 81.6(12) 2_656 . . . ?
Gd1 Gd1 N20 O21 87.2(10) 2_656 . . . ?
Gd1 O1 C1 O1 9.6(6) . . . 2_656 ?
Gd1 O1 C1 C2 -170.4(6) . . . . ?
O1 C1 C2 C3 -47.6(8) 2_656 . . 2_656 ?
O1 C1 C2 C3 132.4(8) . . . 2_656 ?
O1 C1 C2 C3 132.4(8) 2_656 . . . ?
O1 C1 C2 C3 -47.6(8) . . . . ?
C3 C2 C3 F3 177.3(15) 2_656 . . . ?
C1 C2 C3 F3 -2.7(15) . . . . ?
C3 C2 C3 C4 -0.2(10) 2_656 . . . ?
C1 C2 C3 C4 179.8(10) . . . . ?
F3 C3 C4 F4 1(2) . . . . ?
C2 C3 C4 F4 179.0(10) . . . . ?
F3 C3 C4 C5 -177.2(10) . . . . ?
C2 C3 C4 C5 0(2) . . . . ?
F4 C4 C5 C4 -178.7(16) . . . 2_656 ?
C3 C4 C5 C4 -0.2(10) . . . 2_656 ?
F4 C4 C5 C6 1.3(15) . . . . ?
C3 C4 C5 C6 179.8(10) . . . . ?
Gd1 O6 C6 O6 -3.2(6) 1_545 . . 2_656 ?
Gd1 O6 C6 C5 176.8(6) 1_545 . . . ?
C4 C5 C6 O6 52.6(8) 2_656 . . 2_656 ?
C4 C5 C6 O6 -127.4(8) . . . 2_656 ?
C4 C5 C6 O6 -127.4(8) 2_656 . . . ?
C4 C5 C6 O6 52.6(8) . . . . ?
Gd1 O7B C7 O7A -3.9(19) 2_656 . . . ?
Gd1 O7B C7 C8 176.2(12) 2_656 . . . ?
Gd1 O7A C7 O7B 168(2) . . . . ?
Gd1 O7A C7 O7B 3.7(18) 2_656 . . . ?
Gd1 O7A C7 C8 -12(4) . . . . ?
Gd1 O7A C7 C8 -176.4(11) 2_656 . . . ?
Gd1 O7A C7 Gd1 164(4) . . . 2_656 ?
O7B C7 C8 C9 -99.2(18) . . . . ?
O7A C7 C8 C9 80.9(17) . . . . ?
O7B C7 C8 C10 78.5(19) . . . . ?
O7A C7 C8 C10 -101.4(16) . . . . ?
C10 C8 C9 C10 -1(2) . . . 5_666 ?
C7 C8 C9 C10 177.1(12) . . . 5_666 ?
C10 C8 C9 F9 -178.5(11) . . . . ?
C7 C8 C9 F9 -0.7(19) . . . . ?
C9 C8 C10 F10 178.8(12) . . . . ?
C7 C8 C10 F10 1.0(18) . . . . ?
C9 C8 C10 C9 1(2) . . . 5_666 ?
C7 C8 C10 C9 -177.2(12) . . . 5_666 ?
Gd1 O11 C11 N11 156.6(11) . . . . ?
C12 N11 C11 O11 4(3) . . . . ?
C13 N11 C11 O11 -174.5(17) . . . . ?
Gd1 O14 C14 N14 177.0(12) . . . . ?
C16 N14 C14 O14 2(3) . . . . ?
C15 N14 C14 O14 -178.5(14) . . . . ?
C18 N17 C17 O17 173(3) . . . . ?
C19 N17 C17 O17 5(5) . . . . ?

_diffrn_measured_fraction_theta_max 0.699
_diffrn_reflns_theta_full        28.11
_diffrn_measured_fraction_theta_full 0.699
_refine_diff_density_max         2.369
_refine_diff_density_min         -1.766
_refine_diff_density_rms         0.186
####################################################################### 
# 
# 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_cs848
_database_code_depnum_ccdc_archive 'CCDC 958001'
_audit_update_record             
;
2013-08-28 deposited with the CCDC.
2015-02-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H21 F4 N4 O10 Tb'
_chemical_formula_weight         676.30

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'
F F 0.0171 0.0103 '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'
Tb Tb -0.1723 4.1537 '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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   C2/c

loop_
_symmetry_equiv_pos_as_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'
'-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                   22.157(3)
_cell_length_b                   11.3680(13)
_cell_length_c                   20.566(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 111.047(11)
_cell_angle_gamma                90.00
_cell_volume                     4834.6(11)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.858
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2656
_exptl_absorpt_coefficient_mu    3.015
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.1277
_exptl_absorpt_correction_T_max  0.3693
_exptl_absorpt_process_details   'X-Red, X-Shape'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11978
_diffrn_reflns_av_R_equivalents  0.0883
_diffrn_reflns_av_sigmaI/netI    0.0721
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         2.04
_diffrn_reflns_theta_max         27.34
_reflns_number_total             3977
_reflns_number_gt                2827
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0710P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    riding
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3977
_refine_ls_number_parameters     337
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0661
_refine_ls_R_factor_gt           0.0440
_refine_ls_wR_factor_ref         0.1139
_refine_ls_wR_factor_gt          0.1033
_refine_ls_goodness_of_fit_ref   0.924
_refine_ls_restrained_S_all      0.924
_refine_ls_shift/su_max          0.033
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Tb1 Tb 0.403706(14) 0.46488(3) 0.697996(15) 0.0497(5) Uani 1 1 d . . .
F3 F 0.4225(3) 0.0813(5) 0.8045(4) 0.0920(19) Uani 1 1 d . . .
F4 F 0.4217(3) -0.1514(5) 0.8028(4) 0.099(2) Uani 1 1 d . . .
F9 F 0.5006(3) 0.6900(5) 0.5794(3) 0.0899(16) Uani 1 1 d . . .
F10 F 0.5417(3) 0.2881(5) 0.5605(3) 0.0886(16) Uani 1 1 d . . .
O1 O 0.4453(2) 0.2725(4) 0.7277(3) 0.0619(13) Uani 1 1 d . . .
O6 O 0.4461(3) -0.3424(4) 0.7233(3) 0.0658(13) Uani 1 1 d . . .
O7A O 0.5038(3) 0.4662(5) 0.6804(3) 0.0579(12) Uani 1 1 d . . .
O7B O 0.6029(3) 0.4779(7) 0.6848(3) 0.0792(18) Uani 1 1 d . . .
O11 O 0.3116(3) 0.5845(6) 0.6733(3) 0.0736(16) Uani 1 1 d . . .
O14 O 0.3139(3) 0.3425(6) 0.6898(4) 0.0826(19) Uani 1 1 d . . .
O17 O 0.3482(9) -0.0824(19) 0.5944(10) 0.214(7) Uani 1 1 d . . .
O21 O 0.3774(5) 0.3549(6) 0.5883(3) 0.100(2) Uani 1 1 d . . .
O22 O 0.3547(4) 0.4293(9) 0.4854(3) 0.110(3) Uani 1 1 d . . .
O23 O 0.3743(4) 0.5392(7) 0.5761(3) 0.0875(19) Uani 1 1 d . . .
N11 N 0.2278(4) 0.6999(7) 0.6101(4) 0.082(2) Uani 1 1 d . . .
N14 N 0.2531(4) 0.1811(7) 0.6819(4) 0.0719(19) Uani 1 1 d . . .
N17 N 0.3706(7) 0.0536(14) 0.5268(9) 0.137(4) Uani 1 1 d . . .
N20 N 0.3678(4) 0.4404(8) 0.5482(3) 0.074(2) Uani 1 1 d . . .
C1 C 0.5000 0.2246(9) 0.7500 0.054(2) Uani 1 2 d S . .
C2 C 0.5000 0.0898(9) 0.7500 0.055(2) Uani 1 2 d S . .
C3 C 0.4612(4) 0.0251(7) 0.7766(4) 0.0624(17) Uani 1 1 d . . .
C4 C 0.4610(4) -0.0970(7) 0.7760(5) 0.0669(19) Uani 1 1 d . . .
C5 C 0.5000 -0.1586(9) 0.7500 0.061(2) Uani 1 2 d S . .
C6 C 0.5000 -0.2942(8) 0.7500 0.057(2) Uani 1 2 d S . .
C7 C 0.5449(4) 0.4775(7) 0.6517(4) 0.0592(17) Uani 1 1 d . . .
C8 C 0.5214(4) 0.4890(7) 0.5728(4) 0.0590(17) Uani 1 1 d . . .
C9 C 0.5002(4) 0.5946(8) 0.5410(4) 0.0639(17) Uani 1 1 d . . .
C10 C 0.5206(4) 0.3937(8) 0.5309(4) 0.0634(17) Uani 1 1 d . . .
C11 C 0.2895(5) 0.6674(9) 0.6347(6) 0.080(2) Uani 1 1 d . . .
H11 H 0.3182 0.7119 0.6212 0.16(4) Uiso 1 1 calc R . .
C12 C 0.1804(6) 0.6345(12) 0.6299(7) 0.110(4) Uani 1 1 d . . .
H12A H 0.2024 0.5851 0.6691 0.22(2) Uiso 1 1 calc R . .
H12B H 0.1547 0.5867 0.5914 0.22(2) Uiso 1 1 calc R . .
H12C H 0.1530 0.6886 0.6421 0.22(2) Uiso 1 1 calc R . .
C13 C 0.2043(6) 0.7956(11) 0.5627(7) 0.112(4) Uani 1 1 d . . .
H13A H 0.1799 0.8482 0.5803 0.22(2) Uiso 1 1 calc R A 1
H13B H 0.1771 0.7659 0.5181 0.22(2) Uiso 1 1 calc R A 1
H13C H 0.2402 0.8371 0.5578 0.22(2) Uiso 1 1 calc R A 1
C14 C 0.3065(5) 0.2362(9) 0.6851(5) 0.077(2) Uani 1 1 d . . .
H14 H 0.3409 0.1908 0.6838 0.16(4) Uiso 1 1 calc R . .
C15 C 0.2492(6) 0.0540(9) 0.6785(6) 0.090(3) Uani 1 1 d . . .
H15A H 0.2920 0.0214 0.6969 0.22(2) Uiso 1 1 calc R . .
H15B H 0.2285 0.0298 0.6309 0.22(2) Uiso 1 1 calc R . .
H15C H 0.2246 0.0266 0.7055 0.22(2) Uiso 1 1 calc R . .
C16 C 0.1976(6) 0.2498(12) 0.6827(8) 0.111(4) Uani 1 1 d . . .
H16A H 0.2030 0.3304 0.6720 0.22(2) Uiso 1 1 calc R . .
H16B H 0.1945 0.2449 0.7280 0.22(2) Uiso 1 1 calc R . .
H16C H 0.1588 0.2190 0.6485 0.22(2) Uiso 1 1 calc R . .
C17 C 0.3879(11) -0.033(2) 0.5714(12) 0.162(7) Uani 1 1 d . . .
H17 H 0.4304 -0.0595 0.5867 0.16(4) Uiso 1 1 calc R . .
C18 C 0.4191(12) 0.111(2) 0.5067(15) 0.208(11) Uani 1 1 d . . .
H18A H 0.4501 0.1479 0.5466 0.22(2) Uiso 1 1 calc R . .
H18B H 0.3991 0.1686 0.4716 0.22(2) Uiso 1 1 calc R . .
H18C H 0.4405 0.0531 0.4883 0.22(2) Uiso 1 1 calc R . .
C19 C 0.3032(9) 0.1004(19) 0.4982(11) 0.156(6) Uani 1 1 d . . .
H19A H 0.2731 0.0361 0.4854 0.22(2) Uiso 1 1 calc R . .
H19B H 0.2980 0.1478 0.4579 0.22(2) Uiso 1 1 calc R . .
H19C H 0.2951 0.1476 0.5329 0.22(2) Uiso 1 1 calc R . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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 O11 2.351(6) . ?
Tb1 O6 2.367(5) 1_565 ?
Tb1 O1 2.367(5) . ?
Tb1 O7A 2.372(5) . ?
Tb1 O14 2.384(7) . ?
Tb1 O21 2.459(6) . ?
Tb1 O7B 2.471(6) 2_656 ?
Tb1 O23 2.499(6) . ?
Tb1 O7A 2.603(5) 2_656 ?
Tb1 C7 2.889(7) 2_656 ?
Tb1 N20 2.906(7) . ?
F3 C3 1.350(9) . ?
F4 C4 1.338(9) . ?
F9 C9 1.340(10) . ?
F10 C10 1.351(9) . ?
O1 C1 1.256(7) . ?
O6 C6 1.248(7) . ?
O6 Tb1 2.367(5) 1_545 ?
O7A C7 1.257(9) . ?
O7A Tb1 2.603(5) 2_656 ?
O7B C7 1.220(10) . ?
O7B Tb1 2.471(6) 2_656 ?
O11 C11 1.216(12) . ?
O14 C14 1.218(12) . ?
O17 C17 1.27(3) . ?
O21 N20 1.244(10) . ?
O22 N20 1.223(9) . ?
O23 N20 1.247(10) . ?
N11 C11 1.328(12) . ?
N11 C13 1.428(13) . ?
N11 C12 1.458(14) . ?
N14 C14 1.319(12) . ?
N14 C15 1.447(12) . ?
N14 C16 1.463(14) . ?
N17 C17 1.31(2) . ?
N17 C18 1.44(2) . ?
N17 C19 1.49(2) . ?
C1 O1 1.256(7) 2_656 ?
C1 C2 1.532(13) . ?
C2 C3 1.385(9) 2_656 ?
C2 C3 1.385(9) . ?
C3 C4 1.388(11) . ?
C4 C5 1.362(10) . ?
C5 C4 1.362(10) 2_656 ?
C5 C6 1.541(13) . ?
C6 O6 1.248(7) 2_656 ?
C7 C8 1.520(10) . ?
C7 Tb1 2.889(7) 2_656 ?
C8 C9 1.367(11) . ?
C8 C10 1.381(11) . ?
C9 C10 1.388(10) 5_666 ?
C10 C9 1.388(10) 5_666 ?
C11 H11 0.9300 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14 0.9300 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17 0.9300 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 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
O11 Tb1 O6 76.0(2) . 1_565 ?
O11 Tb1 O1 144.8(2) . . ?
O6 Tb1 O1 135.37(18) 1_565 . ?
O11 Tb1 O7A 138.6(2) . . ?
O6 Tb1 O7A 73.08(19) 1_565 . ?
O1 Tb1 O7A 75.33(18) . . ?
O11 Tb1 O14 71.6(2) . . ?
O6 Tb1 O14 144.2(2) 1_565 . ?
O1 Tb1 O14 73.5(2) . . ?
O7A Tb1 O14 142.7(2) . . ?
O11 Tb1 O21 101.2(3) . . ?
O6 Tb1 O21 128.1(2) 1_565 . ?
O1 Tb1 O21 73.1(2) . . ?
O7A Tb1 O21 77.9(3) . . ?
O14 Tb1 O21 73.8(3) . . ?
O11 Tb1 O7B 79.9(2) . 2_656 ?
O6 Tb1 O7B 83.5(2) 1_565 2_656 ?
O1 Tb1 O7B 87.6(2) . 2_656 ?
O7A Tb1 O7B 122.36(18) . 2_656 ?
O14 Tb1 O7B 76.3(3) . 2_656 ?
O21 Tb1 O7B 147.9(2) . 2_656 ?
O11 Tb1 O23 72.2(2) . . ?
O6 Tb1 O23 81.3(2) 1_565 . ?
O1 Tb1 O23 120.6(2) . . ?
O7A Tb1 O23 76.5(2) . . ?
O14 Tb1 O23 102.5(3) . . ?
O21 Tb1 O23 50.3(2) . . ?
O7B Tb1 O23 150.7(2) 2_656 . ?
O11 Tb1 O7A 121.8(2) . 2_656 ?
O6 Tb1 O7A 70.71(18) 1_565 2_656 ?
O1 Tb1 O7A 70.02(18) . 2_656 ?
O7A Tb1 O7A 71.97(18) . 2_656 ?
O14 Tb1 O7A 114.9(2) . 2_656 ?
O21 Tb1 O7A 136.9(2) . 2_656 ?
O7B Tb1 O7A 50.54(17) 2_656 2_656 ?
O23 Tb1 O7A 142.5(2) . 2_656 ?
O11 Tb1 C7 100.4(2) . 2_656 ?
O6 Tb1 C7 75.2(2) 1_565 2_656 ?
O1 Tb1 C7 78.6(2) . 2_656 ?
O7A Tb1 C7 97.6(2) . 2_656 ?
O14 Tb1 C7 95.9(3) . 2_656 ?
O21 Tb1 C7 151.6(2) . 2_656 ?
O7B Tb1 C7 24.8(2) 2_656 2_656 ?
O23 Tb1 C7 156.5(3) . 2_656 ?
O7A Tb1 C7 25.79(19) 2_656 2_656 ?
O11 Tb1 N20 86.6(2) . . ?
O6 Tb1 N20 105.0(2) 1_565 . ?
O1 Tb1 N20 96.8(2) . . ?
O7A Tb1 N20 75.72(19) . . ?
O14 Tb1 N20 88.0(3) . . ?
O21 Tb1 N20 25.1(2) . . ?
O7B Tb1 N20 161.9(2) 2_656 . ?
O23 Tb1 N20 25.3(2) . . ?
O7A Tb1 N20 147.23(19) 2_656 . ?
C7 Tb1 N20 172.8(2) 2_656 . ?
C1 O1 Tb1 136.9(5) . . ?
C6 O6 Tb1 138.2(5) . 1_545 ?
C7 O7A Tb1 161.3(5) . . ?
C7 O7A Tb1 89.9(4) . 2_656 ?
Tb1 O7A Tb1 108.03(18) . 2_656 ?
C7 O7B Tb1 97.2(4) . 2_656 ?
C11 O11 Tb1 134.8(6) . . ?
C14 O14 Tb1 132.1(6) . . ?
N20 O21 Tb1 98.0(5) . . ?
N20 O23 Tb1 95.9(5) . . ?
C11 N11 C13 123.0(10) . . ?
C11 N11 C12 119.8(9) . . ?
C13 N11 C12 117.2(9) . . ?
C14 N14 C15 121.0(9) . . ?
C14 N14 C16 119.2(9) . . ?
C15 N14 C16 119.8(9) . . ?
C17 N17 C18 119(2) . . ?
C17 N17 C19 123.1(18) . . ?
C18 N17 C19 118(2) . . ?
O22 N20 O21 122.6(9) . . ?
O22 N20 O23 121.6(9) . . ?
O21 N20 O23 115.7(7) . . ?
O22 N20 Tb1 178.0(7) . . ?
O21 N20 Tb1 56.9(4) . . ?
O23 N20 Tb1 58.8(4) . . ?
O1 C1 O1 128.6(9) . 2_656 ?
O1 C1 C2 115.7(5) . . ?
O1 C1 C2 115.7(5) 2_656 . ?
C3 C2 C3 115.9(9) 2_656 . ?
C3 C2 C1 122.1(5) 2_656 . ?
C3 C2 C1 122.1(5) . . ?
F3 C3 C2 119.7(7) . . ?
F3 C3 C4 118.4(7) . . ?
C2 C3 C4 121.8(7) . . ?
F4 C4 C5 121.5(8) . . ?
F4 C4 C3 117.3(7) . . ?
C5 C4 C3 121.2(7) . . ?
C4 C5 C4 118.1(10) . 2_656 ?
C4 C5 C6 121.0(5) . . ?
C4 C5 C6 121.0(5) 2_656 . ?
O6 C6 O6 127.9(9) . 2_656 ?
O6 C6 C5 116.1(5) . . ?
O6 C6 C5 116.1(5) 2_656 . ?
O7B C7 O7A 122.3(7) . . ?
O7B C7 C8 119.0(7) . . ?
O7A C7 C8 118.8(7) . . ?
O7B C7 Tb1 58.0(4) . 2_656 ?
O7A C7 Tb1 64.3(4) . 2_656 ?
C8 C7 Tb1 176.4(5) . 2_656 ?
C9 C8 C10 117.7(7) . . ?
C9 C8 C7 120.9(7) . . ?
C10 C8 C7 121.4(7) . . ?
F9 C9 C8 120.0(7) . . ?
F9 C9 C10 118.7(8) . 5_666 ?
C8 C9 C10 121.3(8) . 5_666 ?
F10 C10 C8 119.4(7) . . ?
F10 C10 C9 119.6(8) . 5_666 ?
C8 C10 C9 121.0(8) . 5_666 ?
O11 C11 N11 125.6(9) . . ?
O11 C11 H11 117.2 . . ?
N11 C11 H11 117.2 . . ?
N11 C12 H12A 109.5 . . ?
N11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
N11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N11 C13 H13A 109.5 . . ?
N11 C13 H13B 109.5 . . ?
N11 C13 H13C 109.5 . . ?
O14 C14 N14 124.7(10) . . ?
O14 C14 H14 117.7 . . ?
N14 C14 H14 117.7 . . ?
N14 C15 H15A 109.5 . . ?
N14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
N14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N14 C16 H16A 109.5 . . ?
N14 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
N14 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O17 C17 N17 122(2) . . ?
O17 C17 H17 119.1 . . ?
N17 C17 H17 119.1 . . ?
N17 C18 H18A 109.5 . . ?
N17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
N17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
N17 C19 H19A 109.5 . . ?
N17 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
N17 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 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
O11 Tb1 O1 C1 -166.1(4) . . . . ?
O6 Tb1 O1 C1 -19.1(7) 1_565 . . . ?
O7A Tb1 O1 C1 27.0(5) . . . . ?
O14 Tb1 O1 C1 -173.9(6) . . . . ?
O21 Tb1 O1 C1 108.5(6) . . . . ?
O7B Tb1 O1 C1 -97.4(5) 2_656 . . . ?
O23 Tb1 O1 C1 91.2(6) . . . . ?
O7A Tb1 O1 C1 -48.8(5) 2_656 . . . ?
C7 Tb1 O1 C1 -74.1(5) 2_656 . . . ?
N20 Tb1 O1 C1 100.2(5) . . . . ?
O11 Tb1 O7A C7 -44.3(18) . . . . ?
O6 Tb1 O7A C7 -87.6(17) 1_565 . . . ?
O1 Tb1 O7A C7 124.4(17) . . . . ?
O14 Tb1 O7A C7 90.1(17) . . . . ?
O21 Tb1 O7A C7 48.9(17) . . . . ?
O7B Tb1 O7A C7 -158.2(16) 2_656 . . . ?
O23 Tb1 O7A C7 -2.8(17) . . . . ?
O7A Tb1 O7A C7 -162.3(16) 2_656 . . . ?
C7 Tb1 O7A C7 -159.6(18) 2_656 . . . ?
N20 Tb1 O7A C7 23.3(17) . . . . ?
O11 Tb1 O7A Tb1 118.7(3) . . . 2_656 ?
O6 Tb1 O7A Tb1 75.4(2) 1_565 . . 2_656 ?
O1 Tb1 O7A Tb1 -72.7(2) . . . 2_656 ?
O14 Tb1 O7A Tb1 -106.9(4) . . . 2_656 ?
O21 Tb1 O7A Tb1 -148.1(3) . . . 2_656 ?
O7B Tb1 O7A Tb1 4.8(3) 2_656 . . 2_656 ?
O23 Tb1 O7A Tb1 160.2(3) . . . 2_656 ?
O7A Tb1 O7A Tb1 0.7(3) 2_656 . . 2_656 ?
C7 Tb1 O7A Tb1 3.4(2) 2_656 . . 2_656 ?
N20 Tb1 O7A Tb1 -173.8(3) . . . 2_656 ?
O6 Tb1 O11 C11 57.7(10) 1_565 . . . ?
O1 Tb1 O11 C11 -145.5(9) . . . . ?
O7A Tb1 O11 C11 15.2(11) . . . . ?
O14 Tb1 O11 C11 -137.7(10) . . . . ?
O21 Tb1 O11 C11 -69.1(10) . . . . ?
O7B Tb1 O11 C11 143.5(10) 2_656 . . . ?
O23 Tb1 O11 C11 -27.5(10) . . . . ?
O7A Tb1 O11 C11 113.9(10) 2_656 . . . ?
C7 Tb1 O11 C11 129.5(10) 2_656 . . . ?
N20 Tb1 O11 C11 -48.7(10) . . . . ?
O11 Tb1 O14 C14 166.7(10) . . . . ?
O6 Tb1 O14 C14 -167.2(8) 1_565 . . . ?
O1 Tb1 O14 C14 -18.0(9) . . . . ?
O7A Tb1 O14 C14 16.6(12) . . . . ?
O21 Tb1 O14 C14 58.7(10) . . . . ?
O7B Tb1 O14 C14 -109.5(10) 2_656 . . . ?
O23 Tb1 O14 C14 100.5(10) . . . . ?
O7A Tb1 O14 C14 -76.0(10) 2_656 . . . ?
C7 Tb1 O14 C14 -94.3(10) 2_656 . . . ?
N20 Tb1 O14 C14 79.7(10) . . . . ?
O11 Tb1 O21 N20 55.5(6) . . . . ?
O6 Tb1 O21 N20 -25.4(8) 1_565 . . . ?
O1 Tb1 O21 N20 -160.3(7) . . . . ?
O7A Tb1 O21 N20 -82.2(6) . . . . ?
O14 Tb1 O21 N20 122.4(7) . . . . ?
O7B Tb1 O21 N20 144.3(5) 2_656 . . . ?
O23 Tb1 O21 N20 0.2(5) . . . . ?
O7A Tb1 O21 N20 -128.3(5) 2_656 . . . ?
C7 Tb1 O21 N20 -165.7(5) 2_656 . . . ?
O11 Tb1 O23 N20 -122.3(6) . . . . ?
O6 Tb1 O23 N20 159.8(5) 1_565 . . . ?
O1 Tb1 O23 N20 21.6(6) . . . . ?
O7A Tb1 O23 N20 85.2(5) . . . . ?
O14 Tb1 O23 N20 -56.5(6) . . . . ?
O21 Tb1 O23 N20 -0.2(5) . . . . ?
O7B Tb1 O23 N20 -140.7(5) 2_656 . . . ?
O7A Tb1 O23 N20 118.3(5) 2_656 . . . ?
C7 Tb1 O23 N20 163.0(5) 2_656 . . . ?
Tb1 O21 N20 O22 177.6(8) . . . . ?
Tb1 O21 N20 O23 -0.3(9) . . . . ?
Tb1 O23 N20 O22 -177.7(8) . . . . ?
Tb1 O23 N20 O21 0.3(9) . . . . ?
O11 Tb1 N20 O22 156(21) . . . . ?
O6 Tb1 N20 O22 81(21) 1_565 . . . ?
O1 Tb1 N20 O22 -59(21) . . . . ?
O7A Tb1 N20 O22 14(21) . . . . ?
O14 Tb1 N20 O22 -133(21) . . . . ?
O21 Tb1 N20 O22 -78(21) . . . . ?
O7B Tb1 N20 O22 -162(21) 2_656 . . . ?
O23 Tb1 N20 O22 102(21) . . . . ?
O7A Tb1 N20 O22 4(21) 2_656 . . . ?
C7 Tb1 N20 O22 -9(22) 2_656 . . . ?
O11 Tb1 N20 O21 -125.9(6) . . . . ?
O6 Tb1 N20 O21 159.6(6) 1_565 . . . ?
O1 Tb1 N20 O21 18.9(6) . . . . ?
O7A Tb1 N20 O21 91.8(6) . . . . ?
O14 Tb1 N20 O21 -54.3(6) . . . . ?
O7B Tb1 N20 O21 -84.2(10) 2_656 . . . ?
O23 Tb1 N20 O21 -179.7(9) . . . . ?
O7A Tb1 N20 O21 82.1(7) 2_656 . . . ?
C7 Tb1 N20 O21 69(2) 2_656 . . . ?
O11 Tb1 N20 O23 53.7(5) . . . . ?
O6 Tb1 N20 O23 -20.7(6) 1_565 . . . ?
O1 Tb1 N20 O23 -161.4(5) . . . . ?
O7A Tb1 N20 O23 -88.5(5) . . . . ?
O14 Tb1 N20 O23 125.4(5) . . . . ?
O21 Tb1 N20 O23 179.7(9) . . . . ?
O7B Tb1 N20 O23 95.5(9) 2_656 . . . ?
O7A Tb1 N20 O23 -98.2(6) 2_656 . . . ?
C7 Tb1 N20 O23 -111.4(19) 2_656 . . . ?
Tb1 O1 C1 O1 9.3(4) . . . 2_656 ?
Tb1 O1 C1 C2 -170.7(4) . . . . ?
O1 C1 C2 C3 132.0(5) . . . 2_656 ?
O1 C1 C2 C3 -48.0(5) 2_656 . . 2_656 ?
O1 C1 C2 C3 -48.0(5) . . . . ?
O1 C1 C2 C3 132.0(5) 2_656 . . . ?
C3 C2 C3 F3 179.0(9) 2_656 . . . ?
C1 C2 C3 F3 -1.0(9) . . . . ?
C3 C2 C3 C4 -0.5(6) 2_656 . . . ?
C1 C2 C3 C4 179.5(6) . . . . ?
F3 C3 C4 F4 0.6(13) . . . . ?
C2 C3 C4 F4 -179.9(7) . . . . ?
F3 C3 C4 C5 -178.5(8) . . . . ?
C2 C3 C4 C5 1.0(13) . . . . ?
F4 C4 C5 C4 -179.5(10) . . . 2_656 ?
C3 C4 C5 C4 -0.5(6) . . . 2_656 ?
F4 C4 C5 C6 0.5(10) . . . . ?
C3 C4 C5 C6 179.5(6) . . . . ?
Tb1 O6 C6 O6 -3.3(4) 1_545 . . 2_656 ?
Tb1 O6 C6 C5 176.7(4) 1_545 . . . ?
C4 C5 C6 O6 52.4(5) . . . . ?
C4 C5 C6 O6 -127.6(5) 2_656 . . . ?
C4 C5 C6 O6 -127.6(5) . . . 2_656 ?
C4 C5 C6 O6 52.4(5) 2_656 . . 2_656 ?
Tb1 O7B C7 O7A -3.4(10) 2_656 . . . ?
Tb1 O7B C7 C8 177.7(6) 2_656 . . . ?
Tb1 O7A C7 O7B 167.0(12) . . . . ?
Tb1 O7A C7 O7B 3.2(9) 2_656 . . . ?
Tb1 O7A C7 C8 -14(2) . . . . ?
Tb1 O7A C7 C8 -177.9(7) 2_656 . . . ?
Tb1 O7A C7 Tb1 163.8(17) . . . 2_656 ?
O7B C7 C8 C9 -99.8(10) . . . . ?
O7A C7 C8 C9 81.2(10) . . . . ?
Tb1 C7 C8 C9 -67(10) 2_656 . . . ?
O7B C7 C8 C10 80.3(11) . . . . ?
O7A C7 C8 C10 -98.7(10) . . . . ?
Tb1 C7 C8 C10 113(9) 2_656 . . . ?
C10 C8 C9 F9 -179.3(7) . . . . ?
C7 C8 C9 F9 0.8(12) . . . . ?
C10 C8 C9 C10 -0.9(13) . . . 5_666 ?
C7 C8 C9 C10 179.2(7) . . . 5_666 ?
C9 C8 C10 F10 179.4(7) . . . . ?
C7 C8 C10 F10 -0.7(11) . . . . ?
C9 C8 C10 C9 0.9(13) . . . 5_666 ?
C7 C8 C10 C9 -179.2(7) . . . 5_666 ?
Tb1 O11 C11 N11 156.2(8) . . . . ?
C13 N11 C11 O11 -177.5(11) . . . . ?
C12 N11 C11 O11 0.7(17) . . . . ?
Tb1 O14 C14 N14 179.1(7) . . . . ?
C15 N14 C14 O14 -178.1(10) . . . . ?
C16 N14 C14 O14 1.0(16) . . . . ?
C18 N17 C17 O17 176(2) . . . . ?
C19 N17 C17 O17 -1(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.727
_diffrn_reflns_theta_full        27.34
_diffrn_measured_fraction_theta_full 0.727
_refine_diff_density_max         0.293
_refine_diff_density_min         -0.284
_refine_diff_density_rms         0.023
####################################################################### 
# 
# 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_ms093
_database_code_depnum_ccdc_archive 'CCDC 958002'
_audit_update_record             
;
2013-08-28 deposited with the CCDC.
2015-02-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H21 F4 Ho N4 O10'
_chemical_formula_weight         682.31

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'
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'
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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C2 /c'

loop_
_symmetry_equiv_pos_as_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'
'-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                   22.047(4)
_cell_length_b                   11.3219(15)
_cell_length_c                   20.515(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 111.38(2)
_cell_angle_gamma                90.00
_cell_volume                     4768.4(18)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            pink
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.901
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2671
_exptl_absorpt_coefficient_mu    3.409
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.0884
_exptl_absorpt_correction_T_max  0.2815
_exptl_absorpt_process_details   'X-Red, X-Shape'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10838
_diffrn_reflns_av_R_equivalents  0.1020
_diffrn_reflns_av_sigmaI/netI    0.1077
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         2.69
_diffrn_reflns_theta_max         28.16
_reflns_number_total             4073
_reflns_number_gt                2616
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1206P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    riding
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4073
_refine_ls_number_parameters     335
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1003
_refine_ls_R_factor_gt           0.0698
_refine_ls_wR_factor_ref         0.1798
_refine_ls_wR_factor_gt          0.1689
_refine_ls_goodness_of_fit_ref   0.915
_refine_ls_restrained_S_all      0.915
_refine_ls_shift/su_max          0.009
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Ho1 Ho 0.40318(2) 0.46188(4) 0.69753(2) 0.02057(18) Uani 1 1 d . . .
F3 F 0.4239(5) 0.0781(8) 0.8062(6) 0.053(3) Uani 1 1 d . . .
F4 F 0.4221(5) -0.1541(8) 0.8033(6) 0.056(3) Uani 1 1 d . . .
F9 F 0.4974(5) 0.6897(8) 0.5791(4) 0.052(2) Uani 1 1 d . . .
F10 F 0.5441(4) 0.2877(7) 0.5601(4) 0.046(2) Uani 1 1 d . . .
O1 O 0.4451(4) 0.2716(7) 0.7277(5) 0.0305(19) Uani 1 1 d . . .
O6 O 0.4452(4) -0.3472(7) 0.7239(5) 0.036(2) Uani 1 1 d . . .
O7A O 0.5019(4) 0.4640(8) 0.6800(4) 0.0279(18) Uani 1 1 d . . .
O7B O 0.6031(4) 0.4746(10) 0.6868(5) 0.040(2) Uani 1 1 d . . .
O11 O 0.3114(5) 0.5817(9) 0.6733(5) 0.038(2) Uani 1 1 d . . .
O14 O 0.3143(5) 0.3405(9) 0.6890(7) 0.047(3) Uani 1 1 d . . .
O17 O 0.3513(10) -0.085(2) 0.5951(12) 0.128(8) Uani 1 1 d . . .
O21 O 0.3788(6) 0.3495(10) 0.5885(6) 0.060(3) Uani 1 1 d . . .
O22 O 0.3557(6) 0.4231(13) 0.4854(5) 0.067(4) Uani 1 1 d . . .
O23 O 0.3732(6) 0.5355(10) 0.5760(6) 0.051(3) Uani 1 1 d . . .
N11 N 0.2273(5) 0.6976(11) 0.6097(7) 0.043(3) Uani 1 1 d . . .
N14 N 0.2550(6) 0.1773(12) 0.6830(7) 0.041(3) Uani 1 1 d . . .
N17 N 0.3718(8) 0.0538(16) 0.5261(10) 0.070(4) Uani 1 1 d . . .
N20 N 0.3679(5) 0.4360(11) 0.5478(5) 0.038(3) Uani 1 1 d . . .
C1 C 0.5000 0.2212(13) 0.7500 0.025(3) Uani 1 2 d S . .
C2 C 0.5000 0.0876(15) 0.7500 0.027(3) Uani 1 2 d S . .
C3 C 0.4612(6) 0.0218(10) 0.7772(7) 0.029(3) Uani 1 1 d . . .
C4 C 0.4606(6) -0.0989(11) 0.7767(7) 0.031(3) Uani 1 1 d . . .
C5 C 0.5000 -0.1649(15) 0.7500 0.027(3) Uani 1 2 d S . .
C6 C 0.5000 -0.2977(15) 0.7500 0.030(4) Uani 1 2 d S . .
C7 C 0.5452(5) 0.4762(12) 0.6529(5) 0.026(3) Uani 1 1 d . . .
C8 C 0.5209(5) 0.4888(12) 0.5731(6) 0.028(3) Uani 1 1 d . . .
C9 C 0.4982(6) 0.5944(12) 0.5410(6) 0.033(3) Uani 1 1 d . . .
C10 C 0.5228(6) 0.3934(12) 0.5309(6) 0.032(3) Uani 1 1 d . . .
C11 C 0.2880(6) 0.6654(13) 0.6321(7) 0.038(3) Uani 1 1 d . . .
H11 H 0.3161 0.7077 0.6162 0.07(3) Uiso 1 1 calc R . .
C12 C 0.1799(8) 0.6364(19) 0.6303(10) 0.065(5) Uani 1 1 d . . .
H12A H 0.1976 0.5622 0.6514 0.073(14) Uiso 1 1 calc R . .
H12B H 0.1414 0.6226 0.5899 0.073(14) Uiso 1 1 calc R . .
H12C H 0.1692 0.6836 0.6635 0.073(14) Uiso 1 1 calc R . .
C13 C 0.2028(8) 0.7935(16) 0.5591(10) 0.060(5) Uani 1 1 d . . .
H13A H 0.2381 0.8267 0.5483 0.073(14) Uiso 1 1 calc R . .
H13B H 0.1838 0.8535 0.5787 0.073(14) Uiso 1 1 calc R . .
H13C H 0.1704 0.7631 0.5171 0.073(14) Uiso 1 1 calc R . .
C14 C 0.3070(7) 0.2317(14) 0.6839(8) 0.040(3) Uani 1 1 d . . .
H14 H 0.3409 0.1865 0.6806 0.07(3) Uiso 1 1 calc R . .
C15 C 0.2487(8) 0.0503(14) 0.6784(9) 0.050(4) Uani 1 1 d . . .
H15A H 0.2908 0.0153 0.6882 0.073(14) Uiso 1 1 calc R . .
H15B H 0.2203 0.0284 0.6321 0.073(14) Uiso 1 1 calc R . .
H15C H 0.2309 0.0226 0.7119 0.073(14) Uiso 1 1 calc R . .
C16 C 0.1978(7) 0.2406(15) 0.6862(10) 0.055(4) Uani 1 1 d . . .
H16A H 0.2115 0.3138 0.7108 0.073(14) Uiso 1 1 calc R . .
H16B H 0.1768 0.1929 0.7104 0.073(14) Uiso 1 1 calc R . .
H16C H 0.1679 0.2562 0.6396 0.073(14) Uiso 1 1 calc R . .
C17 C 0.3873(12) -0.035(2) 0.5706(13) 0.086(7) Uani 1 1 d . . .
H17 H 0.4300 -0.0620 0.5850 0.07(3) Uiso 1 1 calc R . .
C18 C 0.4188(13) 0.110(2) 0.5033(17) 0.108(9) Uani 1 1 d . . .
H18A H 0.4279 0.1876 0.5231 0.073(14) Uiso 1 1 calc R . .
H18B H 0.4019 0.1153 0.4531 0.073(14) Uiso 1 1 calc R . .
H18C H 0.4582 0.0641 0.5184 0.073(14) Uiso 1 1 calc R . .
C19 C 0.3047(11) 0.096(2) 0.4980(14) 0.089(7) Uani 1 1 d . . .
H19A H 0.2828 0.0626 0.4524 0.073(14) Uiso 1 1 calc R . .
H19B H 0.3045 0.1806 0.4945 0.073(14) Uiso 1 1 calc R . .
H19C H 0.2827 0.0728 0.5286 0.073(14) Uiso 1 1 calc R . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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 O7A 2.331(8) . ?
Ho1 O11 2.334(10) . ?
Ho1 O1 2.336(8) . ?
Ho1 O6 2.337(9) 1_565 ?
Ho1 O14 2.347(10) . ?
Ho1 O7B 2.432(9) 2_656 ?
Ho1 O21 2.457(11) . ?
Ho1 O23 2.479(11) . ?
Ho1 O7A 2.619(9) 2_656 ?
Ho1 C7 2.863(10) 2_656 ?
Ho1 N20 2.896(10) . ?
Ho1 Ho1 4.0199(11) 2_656 ?
F3 C3 1.339(13) . ?
F4 C4 1.323(14) . ?
F9 C9 1.336(15) . ?
F10 C10 1.345(15) . ?
O1 C1 1.264(10) . ?
O6 C6 1.260(11) . ?
O6 Ho1 2.337(9) 1_545 ?
O7A C7 1.277(13) . ?
O7A Ho1 2.619(9) 2_656 ?
O7B C7 1.211(14) . ?
O7B Ho1 2.432(9) 2_656 ?
O11 C11 1.249(17) . ?
O14 C14 1.242(19) . ?
O17 C17 1.22(3) . ?
O21 N20 1.253(16) . ?
O22 N20 1.218(14) . ?
O23 N20 1.252(16) . ?
N11 C11 1.298(16) . ?
N11 C12 1.440(19) . ?
N11 C13 1.46(2) . ?
N14 C14 1.294(18) . ?
N14 C15 1.445(19) . ?
N14 C16 1.473(19) . ?
N17 C17 1.32(3) . ?
N17 C18 1.43(3) . ?
N17 C19 1.46(3) . ?
C1 O1 1.264(10) 2_656 ?
C1 C2 1.51(2) . ?
C2 C3 1.396(14) 2_656 ?
C2 C3 1.396(14) . ?
C3 C4 1.366(17) . ?
C4 C5 1.399(15) . ?
C5 C4 1.399(15) 2_656 ?
C5 C6 1.50(2) . ?
C6 O6 1.260(11) 2_656 ?
C7 C8 1.532(14) . ?
C7 Ho1 2.863(10) 2_656 ?
C8 C9 1.368(18) . ?
C8 C10 1.394(18) . ?
C9 C10 1.383(16) 5_666 ?
C10 C9 1.383(16) 5_666 ?
C11 H11 0.9300 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14 0.9300 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17 0.9300 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 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
O7A Ho1 O11 138.3(3) . . ?
O7A Ho1 O1 75.5(3) . . ?
O11 Ho1 O1 145.2(3) . . ?
O7A Ho1 O6 73.3(3) . 1_565 ?
O11 Ho1 O6 75.6(3) . 1_565 ?
O1 Ho1 O6 135.0(3) . 1_565 ?
O7A Ho1 O14 142.7(3) . . ?
O11 Ho1 O14 71.9(4) . . ?
O1 Ho1 O14 73.7(3) . . ?
O6 Ho1 O14 144.0(3) 1_565 . ?
O7A Ho1 O7B 122.6(3) . 2_656 ?
O11 Ho1 O7B 79.7(3) . 2_656 ?
O1 Ho1 O7B 87.4(3) . 2_656 ?
O6 Ho1 O7B 83.0(3) 1_565 2_656 ?
O14 Ho1 O7B 76.4(4) . 2_656 ?
O7A Ho1 O21 76.8(4) . . ?
O11 Ho1 O21 102.8(4) . . ?
O1 Ho1 O21 72.4(4) . . ?
O6 Ho1 O21 128.8(3) 1_565 . ?
O14 Ho1 O21 74.3(4) . . ?
O7B Ho1 O21 148.0(4) 2_656 . ?
O7A Ho1 O23 76.3(3) . . ?
O11 Ho1 O23 72.4(3) . . ?
O1 Ho1 O23 120.7(3) . . ?
O6 Ho1 O23 81.9(4) 1_565 . ?
O14 Ho1 O23 102.3(4) . . ?
O7B Ho1 O23 150.8(3) 2_656 . ?
O21 Ho1 O23 50.9(4) . . ?
O7A Ho1 O7A 71.5(3) . 2_656 ?
O11 Ho1 O7A 121.8(3) . 2_656 ?
O1 Ho1 O7A 69.8(3) . 2_656 ?
O6 Ho1 O7A 70.0(3) 1_565 2_656 ?
O14 Ho1 O7A 115.5(4) . 2_656 ?
O7B Ho1 O7A 51.2(3) 2_656 2_656 ?
O21 Ho1 O7A 135.3(4) . 2_656 ?
O23 Ho1 O7A 142.0(3) . 2_656 ?
O7A Ho1 C7 97.8(3) . 2_656 ?
O11 Ho1 C7 99.8(3) . 2_656 ?
O1 Ho1 C7 78.7(3) . 2_656 ?
O6 Ho1 C7 74.4(4) 1_565 2_656 ?
O14 Ho1 C7 96.2(4) . 2_656 ?
O7B Ho1 C7 24.8(3) 2_656 2_656 ?
O21 Ho1 C7 151.1(4) . 2_656 ?
O23 Ho1 C7 156.2(4) . 2_656 ?
O7A Ho1 C7 26.5(3) 2_656 2_656 ?
O7A Ho1 N20 75.1(3) . . ?
O11 Ho1 N20 87.5(3) . . ?
O1 Ho1 N20 96.6(3) . . ?
O6 Ho1 N20 105.6(3) 1_565 . ?
O14 Ho1 N20 88.2(4) . . ?
O7B Ho1 N20 162.3(3) 2_656 . ?
O21 Ho1 N20 25.4(4) . . ?
O23 Ho1 N20 25.5(3) . . ?
O7A Ho1 N20 146.1(3) 2_656 . ?
C7 Ho1 N20 172.4(3) 2_656 . ?
C1 O1 Ho1 138.3(8) . . ?
C6 O6 Ho1 138.3(9) . 1_545 ?
C7 O7A Ho1 163.2(8) . . ?
C7 O7A Ho1 87.5(6) . 2_656 ?
Ho1 O7A Ho1 108.5(3) . 2_656 ?
C7 O7B Ho1 98.0(7) . 2_656 ?
C11 O11 Ho1 134.3(9) . . ?
C14 O14 Ho1 131.8(9) . . ?
N20 O21 Ho1 97.3(8) . . ?
N20 O23 Ho1 96.2(8) . . ?
C11 N11 C12 121.7(13) . . ?
C11 N11 C13 121.8(13) . . ?
C12 N11 C13 116.4(12) . . ?
C14 N14 C15 122.6(14) . . ?
C14 N14 C16 122.4(14) . . ?
C15 N14 C16 115.0(12) . . ?
C17 N17 C18 122(2) . . ?
C17 N17 C19 119.5(19) . . ?
C18 N17 C19 118(2) . . ?
O22 N20 O23 122.8(13) . . ?
O22 N20 O21 121.5(13) . . ?
O23 N20 O21 115.6(10) . . ?
O22 N20 Ho1 177.2(10) . . ?
O23 N20 Ho1 58.3(6) . . ?
O21 N20 Ho1 57.3(6) . . ?
O1 C1 O1 126.3(14) 2_656 . ?
O1 C1 C2 116.9(7) 2_656 . ?
O1 C1 C2 116.9(7) . . ?
C3 C2 C3 115.5(15) 2_656 . ?
C3 C2 C1 122.2(8) 2_656 . ?
C3 C2 C1 122.2(8) . . ?
F3 C3 C4 118.4(10) . . ?
F3 C3 C2 119.3(11) . . ?
C4 C3 C2 122.3(11) . . ?
F4 C4 C3 118.3(11) . . ?
F4 C4 C5 119.5(12) . . ?
C3 C4 C5 122.2(11) . . ?
C4 C5 C4 115.4(16) 2_656 . ?
C4 C5 C6 122.3(8) 2_656 . ?
C4 C5 C6 122.3(8) . . ?
O6 C6 O6 127.3(16) 2_656 . ?
O6 C6 C5 116.4(8) 2_656 . ?
O6 C6 C5 116.4(8) . . ?
O7B C7 O7A 123.2(10) . . ?
O7B C7 C8 120.0(10) . . ?
O7A C7 C8 116.7(10) . . ?
O7B C7 Ho1 57.3(6) . 2_656 ?
O7A C7 Ho1 66.1(6) . 2_656 ?
C8 C7 Ho1 176.6(8) . 2_656 ?
C9 C8 C10 117.8(11) . . ?
C9 C8 C7 121.3(12) . . ?
C10 C8 C7 120.8(11) . . ?
F9 C9 C8 120.3(10) . . ?
F9 C9 C10 118.2(12) . 5_666 ?
C8 C9 C10 121.5(12) . 5_666 ?
F10 C10 C9 119.4(12) . 5_666 ?
F10 C10 C8 119.9(10) . . ?
C9 C10 C8 120.7(12) 5_666 . ?
O11 C11 N11 124.8(13) . . ?
O11 C11 H11 117.6 . . ?
N11 C11 H11 117.6 . . ?
N11 C12 H12A 109.5 . . ?
N11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
N11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N11 C13 H13A 109.5 . . ?
N11 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
N11 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O14 C14 N14 124.1(14) . . ?
O14 C14 H14 117.9 . . ?
N14 C14 H14 117.9 . . ?
N14 C15 H15A 109.5 . . ?
N14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
N14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N14 C16 H16A 109.5 . . ?
N14 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
N14 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O17 C17 N17 127(2) . . ?
O17 C17 H17 116.6 . . ?
N17 C17 H17 116.6 . . ?
N17 C18 H18A 109.5 . . ?
N17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
N17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
N17 C19 H19A 109.5 . . ?
N17 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
N17 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 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











O7A Ho1 O1 C1 26.4(8) . . . . ?
O11 Ho1 O1 C1 -165.9(7) . . . . ?
O6 Ho1 O1 C1 -20.9(11) 1_565 . . . ?
O14 Ho1 O1 C1 -174.8(10) . . . . ?
O7B Ho1 O1 C1 -98.3(9) 2_656 . . . ?
O21 Ho1 O1 C1 106.9(9) . . . . ?
O23 Ho1 O1 C1 90.4(9) . . . . ?
O7A Ho1 O1 C1 -48.9(8) 2_656 . . . ?
C7 Ho1 O1 C1 -74.8(9) 2_656 . . . ?
N20 Ho1 O1 C1 99.1(9) . . . . ?
O11 Ho1 O7A C7 -42(3) . . . . ?
O1 Ho1 O7A C7 127(3) . . . . ?
O6 Ho1 O7A C7 -86(3) 1_565 . . . ?
O14 Ho1 O7A C7 92(3) . . . . ?
O7B Ho1 O7A C7 -156(3) 2_656 . . . ?
O21 Ho1 O7A C7 52(3) . . . . ?
O23 Ho1 O7A C7 0(3) . . . . ?
O7A Ho1 O7A C7 -160(3) 2_656 . . . ?
C7 Ho1 O7A C7 -157(3) 2_656 . . . ?
N20 Ho1 O7A C7 26(3) . . . . ?
O11 Ho1 O7A Ho1 118.5(5) . . . 2_656 ?
O1 Ho1 O7A Ho1 -72.0(3) . . . 2_656 ?
O6 Ho1 O7A Ho1 75.1(4) 1_565 . . 2_656 ?
O14 Ho1 O7A Ho1 -107.0(6) . . . 2_656 ?
O7B Ho1 O7A Ho1 5.2(5) 2_656 . . 2_656 ?
O21 Ho1 O7A Ho1 -146.9(4) . . . 2_656 ?
O23 Ho1 O7A Ho1 160.7(4) . . . 2_656 ?
O7A Ho1 O7A Ho1 1.1(4) 2_656 . . 2_656 ?
C7 Ho1 O7A Ho1 4.1(4) 2_656 . . 2_656 ?
N20 Ho1 O7A Ho1 -173.1(4) . . . 2_656 ?
O7A Ho1 O11 C11 17.9(16) . . . . ?
O1 Ho1 O11 C11 -144.1(12) . . . . ?
O6 Ho1 O11 C11 60.6(13) 1_565 . . . ?
O14 Ho1 O11 C11 -135.1(14) . . . . ?
O7B Ho1 O11 C11 146.0(14) 2_656 . . . ?
O21 Ho1 O11 C11 -66.6(14) . . . . ?
O23 Ho1 O11 C11 -25.3(13) . . . . ?
O7A Ho1 O11 C11 115.6(13) 2_656 . . . ?
C7 Ho1 O11 C11 131.5(14) 2_656 . . . ?
N20 Ho1 O11 C11 -46.2(13) . . . . ?
O7A Ho1 O14 C14 16.7(17) . . . . ?
O11 Ho1 O14 C14 166.7(15) . . . . ?
O1 Ho1 O14 C14 -18.6(13) . . . . ?
O6 Ho1 O14 C14 -166.7(12) 1_565 . . . ?
O7B Ho1 O14 C14 -109.9(14) 2_656 . . . ?
O21 Ho1 O14 C14 57.2(14) . . . . ?
O23 Ho1 O14 C14 100.1(14) . . . . ?
O7A Ho1 O14 C14 -76.0(14) 2_656 . . . ?
C7 Ho1 O14 C14 -94.9(14) 2_656 . . . ?
N20 Ho1 O14 C14 78.8(14) . . . . ?
O7A Ho1 O21 N20 -82.9(9) . . . . ?
O11 Ho1 O21 N20 54.2(9) . . . . ?
O1 Ho1 O21 N20 -161.6(9) . . . . ?
O6 Ho1 O21 N20 -27.5(11) 1_565 . . . ?
O14 Ho1 O21 N20 120.9(9) . . . . ?
O7B Ho1 O21 N20 145.2(8) 2_656 . . . ?
O23 Ho1 O21 N20 0.0(8) . . . . ?
O7A Ho1 O21 N20 -128.5(8) 2_656 . . . ?
C7 Ho1 O21 N20 -165.2(7) 2_656 . . . ?
O7A Ho1 O23 N20 84.0(8) . . . . ?
O11 Ho1 O23 N20 -124.0(9) . . . . ?
O1 Ho1 O23 N20 20.4(9) . . . . ?
O6 Ho1 O23 N20 158.6(8) 1_565 . . . ?
O14 Ho1 O23 N20 -57.8(8) . . . . ?
O7B Ho1 O23 N20 -141.7(8) 2_656 . . . ?
O21 Ho1 O23 N20 0.0(8) . . . . ?
O7A Ho1 O23 N20 116.6(8) 2_656 . . . ?
C7 Ho1 O23 N20 162.1(8) 2_656 . . . ?
Ho1 O23 N20 O22 -177.0(12) . . . . ?
Ho1 O23 N20 O21 0.1(13) . . . . ?
Ho1 O21 N20 O22 177.0(11) . . . . ?
Ho1 O21 N20 O23 -0.1(13) . . . . ?
O7A Ho1 N20 O23 -89.4(8) . . . . ?
O11 Ho1 N20 O23 52.3(8) . . . . ?
O1 Ho1 N20 O23 -162.5(8) . . . . ?
O6 Ho1 N20 O23 -22.0(9) 1_565 . . . ?
O14 Ho1 N20 O23 124.2(8) . . . . ?
O7B Ho1 N20 O23 95.4(13) 2_656 . . . ?
O21 Ho1 N20 O23 179.9(14) . . . . ?
O7A Ho1 N20 O23 -99.3(9) 2_656 . . . ?
O7A Ho1 N20 O21 90.6(9) . . . . ?
O11 Ho1 N20 O21 -127.7(9) . . . . ?
O1 Ho1 N20 O21 17.6(9) . . . . ?
O6 Ho1 N20 O21 158.1(9) 1_565 . . . ?
O14 Ho1 N20 O21 -55.7(9) . . . . ?
O7B Ho1 N20 O21 -84.5(15) 2_656 . . . ?
O23 Ho1 N20 O21 -179.9(14) . . . . ?
O7A Ho1 N20 O21 80.7(10) 2_656 . . . ?
Ho1 O1 C1 O1 10.0(6) . . . 2_656 ?
Ho1 O1 C1 C2 -170.0(6) . . . . ?
O1 C1 C2 C3 -48.4(8) 2_656 . . 2_656 ?
O1 C1 C2 C3 131.6(8) . . . 2_656 ?
O1 C1 C2 C3 131.6(8) 2_656 . . . ?
O1 C1 C2 C3 -48.4(8) . . . . ?
C3 C2 C3 F3 178.0(15) 2_656 . . . ?
C1 C2 C3 F3 -2.0(15) . . . . ?
C3 C2 C3 C4 -0.6(10) 2_656 . . . ?
C1 C2 C3 C4 179.4(10) . . . . ?
F3 C3 C4 F4 2(2) . . . . ?
C2 C3 C4 F4 -179.7(11) . . . . ?
F3 C3 C4 C5 -177.4(11) . . . . ?
C2 C3 C4 C5 1(2) . . . . ?
F4 C4 C5 C4 -179.6(15) . . . 2_656 ?
C3 C4 C5 C4 -0.6(10) . . . 2_656 ?
F4 C4 C5 C6 0.4(15) . . . . ?
C3 C4 C5 C6 179.4(10) . . . . ?
Ho1 O6 C6 O6 -4.8(6) 1_545 . . 2_656 ?
Ho1 O6 C6 C5 175.2(6) 1_545 . . . ?
C4 C5 C6 O6 51.7(8) 2_656 . . 2_656 ?
C4 C5 C6 O6 -128.3(8) . . . 2_656 ?
C4 C5 C6 O6 -128.3(8) 2_656 . . . ?
C4 C5 C6 O6 51.7(8) . . . . ?
Ho1 O7B C7 O7A -4.7(15) 2_656 . . . ?
Ho1 O7B C7 C8 177.6(11) 2_656 . . . ?
Ho1 O7A C7 O7B 166(2) . . . . ?
Ho1 O7A C7 O7B 4.3(14) 2_656 . . . ?
Ho1 O7A C7 C8 -16(4) . . . . ?
Ho1 O7A C7 C8 -177.9(11) 2_656 . . . ?
Ho1 O7A C7 Ho1 162(3) . . . 2_656 ?
O7B C7 C8 C9 -102.0(16) . . . . ?
O7A C7 C8 C9 80.2(16) . . . . ?
O7B C7 C8 C10 76.3(17) . . . . ?
O7A C7 C8 C10 -101.5(14) . . . . ?
C10 C8 C9 F9 -177.7(11) . . . . ?
C7 C8 C9 F9 0.6(18) . . . . ?
C10 C8 C9 C10 1(2) . . . 5_666 ?
C7 C8 C9 C10 178.9(11) . . . 5_666 ?
C9 C8 C10 F10 -179.4(11) . . . . ?
C7 C8 C10 F10 2.3(17) . . . . ?
C9 C8 C10 C9 -1(2) . . . 5_666 ?
C7 C8 C10 C9 -178.9(11) . . . 5_666 ?
Ho1 O11 C11 N11 157.1(11) . . . . ?
C12 N11 C11 O11 -1(2) . . . . ?
C13 N11 C11 O11 -177.4(15) . . . . ?
Ho1 O14 C14 N14 176.6(11) . . . . ?
C15 N14 C14 O14 -178.7(14) . . . . ?
C16 N14 C14 O14 2(2) . . . . ?
C18 N17 C17 O17 177(3) . . . . ?
C19 N17 C17 O17 -4(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.697
_diffrn_reflns_theta_full        28.16
_diffrn_measured_fraction_theta_full 0.697
_refine_diff_density_max         3.954
_refine_diff_density_min         -3.225
_refine_diff_density_rms         0.267
####################################################################### 
# 
# 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_ms094
_database_code_depnum_ccdc_archive 'CCDC 958003'
_audit_update_record             
;
2013-08-28 deposited with the CCDC.
2015-02-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H21 F4 N4 O10 Tm'
_chemical_formula_weight         686.31

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'
F F 0.0171 0.0103 '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'
Tm Tm -0.3139 5.2483 '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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C2 /c'

loop_
_symmetry_equiv_pos_as_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'
'-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                   22.007(2)
_cell_length_b                   11.2742(10)
_cell_length_c                   20.484(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 111.459(8)
_cell_angle_gamma                90.00
_cell_volume                     4730.0(8)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.70
_exptl_crystal_size_mid          0.50
_exptl_crystal_size_min          0.30
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.928
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2687
_exptl_absorpt_coefficient_mu    3.842
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.2283
_exptl_absorpt_correction_T_max  0.5370
_exptl_absorpt_process_details   'X-Red, X-Shape'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            17808
_diffrn_reflns_av_R_equivalents  0.0886
_diffrn_reflns_av_sigmaI/netI    0.0514
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         2.06
_diffrn_reflns_theta_max         27.22
_reflns_number_total             3914
_reflns_number_gt                3493
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0504P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    riding
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.00158(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3914
_refine_ls_number_parameters     336
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0325
_refine_ls_R_factor_gt           0.0289
_refine_ls_wR_factor_ref         0.0790
_refine_ls_wR_factor_gt          0.0766
_refine_ls_goodness_of_fit_ref   1.037
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Tm1 Tm 0.403400(6) 0.462550(12) 0.697793(7) 0.01959(9) Uani 1 1 d . . .
F3 F 0.42353(17) 0.0802(3) 0.8063(2) 0.0518(8) Uani 1 1 d . . .
F4 F 0.42210(16) -0.1539(2) 0.8044(2) 0.0548(8) Uani 1 1 d . . .
F9 F 0.49648(15) 0.6909(2) 0.57872(12) 0.0490(7) Uani 1 1 d . . .
F10 F 0.54418(13) 0.2877(2) 0.56100(12) 0.0438(6) Uani 1 1 d . . .
O1 O 0.44530(11) 0.2731(2) 0.72866(15) 0.0296(6) Uani 1 1 d . . .
O6 O 0.44503(13) -0.3468(2) 0.72344(16) 0.0321(6) Uani 1 1 d . . .
O7A O 0.50178(15) 0.4641(2) 0.67981(16) 0.0277(6) Uani 1 1 d . . .
O7B O 0.60271(15) 0.4761(3) 0.68761(17) 0.0418(8) Uani 1 1 d . . .
O11 O 0.31191(15) 0.5804(3) 0.67372(18) 0.0373(7) Uani 1 1 d . . .
O14 O 0.31462(16) 0.3423(3) 0.6891(2) 0.0441(8) Uani 1 1 d . . .
O17 O 0.3520(4) -0.0813(7) 0.5966(4) 0.118(2) Uani 1 1 d . . .
O21 O 0.3778(2) 0.3495(3) 0.59003(17) 0.0605(11) Uani 1 1 d . . .
O22 O 0.3552(2) 0.4222(5) 0.48608(17) 0.0650(11) Uani 1 1 d . . .
O23 O 0.3735(2) 0.5365(3) 0.5767(2) 0.0491(10) Uani 1 1 d . . .
N11 N 0.22841(17) 0.6987(3) 0.61020(19) 0.0386(8) Uani 1 1 d . . .
N14 N 0.25432(17) 0.1784(3) 0.6823(2) 0.0375(9) Uani 1 1 d . . .
N17 N 0.3713(3) 0.0532(5) 0.5252(3) 0.0704(16) Uani 1 1 d . . .
N20 N 0.36804(19) 0.4354(4) 0.5487(2) 0.0409(9) Uani 1 1 d . . .
C1 C 0.5000 0.2250(4) 0.7500 0.0226(10) Uani 1 2 d S . .
C2 C 0.5000 0.0890(4) 0.7500 0.0248(10) Uani 1 2 d S . .
C3 C 0.4615(2) 0.0242(3) 0.7766(3) 0.0298(9) Uani 1 1 d . . .
C4 C 0.46066(19) -0.0990(3) 0.7763(2) 0.0309(8) Uani 1 1 d . . .
C5 C 0.5000 -0.1633(4) 0.7500 0.0264(11) Uani 1 2 d S . .
C6 C 0.5000 -0.2987(5) 0.7500 0.0278(11) Uani 1 2 d S . .
C7 C 0.5434(2) 0.4764(3) 0.6523(2) 0.0262(8) Uani 1 1 d . . .
C8 C 0.52115(18) 0.4888(4) 0.57371(19) 0.0254(7) Uani 1 1 d . . .
C9 C 0.4978(2) 0.5953(4) 0.54026(19) 0.0306(8) Uani 1 1 d . . .
C10 C 0.52244(18) 0.3943(3) 0.53147(19) 0.0292(7) Uani 1 1 d . . .
C11 C 0.2905(2) 0.6656(4) 0.6334(2) 0.0371(9) Uani 1 1 d . . .
H11 H 0.3194 0.7083 0.6188 0.066(10) Uiso 1 1 calc R . .
C12 C 0.1810(2) 0.6361(6) 0.6311(3) 0.0586(14) Uani 1 1 d . . .
H12A H 0.2015 0.5691 0.6596 0.107(7) Uiso 1 1 calc R . .
H12B H 0.1458 0.6091 0.5901 0.107(7) Uiso 1 1 calc R . .
H12C H 0.1642 0.6884 0.6575 0.107(7) Uiso 1 1 calc R . .
C13 C 0.2038(3) 0.7953(5) 0.5607(3) 0.0623(15) Uani 1 1 d . . .
H13A H 0.2395 0.8335 0.5529 0.107(7) Uiso 1 1 calc R . .
H13B H 0.1817 0.8516 0.5793 0.107(7) Uiso 1 1 calc R . .
H13C H 0.1738 0.7645 0.5171 0.107(7) Uiso 1 1 calc R . .
C14 C 0.3072(2) 0.2328(4) 0.6833(2) 0.0377(10) Uani 1 1 d . . .
H14 H 0.3411 0.1873 0.6796 0.066(10) Uiso 1 1 calc R . .
C15 C 0.2487(3) 0.0498(4) 0.6773(3) 0.0522(14) Uani 1 1 d . . .
H15A H 0.2891 0.0166 0.6778 0.107(7) Uiso 1 1 calc R . .
H15B H 0.2141 0.0284 0.6344 0.107(7) Uiso 1 1 calc R . .
H15C H 0.2394 0.0196 0.7164 0.107(7) Uiso 1 1 calc R . .
C16 C 0.1984(2) 0.2416(5) 0.6846(3) 0.0575(14) Uani 1 1 d . . .
H16A H 0.2099 0.3230 0.6966 0.107(7) Uiso 1 1 calc R . .
H16B H 0.1842 0.2063 0.7193 0.107(7) Uiso 1 1 calc R . .
H16C H 0.1637 0.2375 0.6395 0.107(7) Uiso 1 1 calc R . .
C17 C 0.3873(4) -0.0331(7) 0.5710(5) 0.085(3) Uani 1 1 d . . .
H17 H 0.4301 -0.0603 0.5855 0.066(10) Uiso 1 1 calc R . .
C18 C 0.4182(4) 0.1134(9) 0.5016(6) 0.113(3) Uani 1 1 d . . .
H18A H 0.4163 0.1972 0.5088 0.107(7) Uiso 1 1 calc R . .
H18B H 0.4078 0.0977 0.4527 0.107(7) Uiso 1 1 calc R . .
H18C H 0.4613 0.0848 0.5279 0.107(7) Uiso 1 1 calc R . .
C19 C 0.3045(3) 0.0970(7) 0.4978(5) 0.086(2) Uani 1 1 d . . .
H19A H 0.2878 0.0925 0.4475 0.107(7) Uiso 1 1 calc R . .
H19B H 0.3037 0.1780 0.5120 0.107(7) Uiso 1 1 calc R . .
H19C H 0.2780 0.0495 0.5157 0.107(7) Uiso 1 1 calc R . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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 O11 2.310(3) . ?
Tm1 O6 2.320(3) 1_565 ?
Tm1 O1 2.321(2) . ?
Tm1 O7A 2.325(3) . ?
Tm1 O14 2.331(3) . ?
Tm1 O7B 2.405(3) 2_656 ?
Tm1 O21 2.430(3) . ?
Tm1 O23 2.468(4) . ?
Tm1 O7A 2.610(3) 2_656 ?
Tm1 C7 2.863(4) 2_656 ?
Tm1 N20 2.879(4) . ?
Tm1 Tm1 3.9998(5) 2_656 ?
F3 C3 1.355(5) . ?
F4 C4 1.338(5) . ?
F9 C9 1.342(5) . ?
F10 C10 1.351(4) . ?
O1 C1 1.245(3) . ?
O6 C6 1.254(3) . ?
O6 Tm1 2.320(2) 1_545 ?
O7A C7 1.247(6) . ?
O7A Tm1 2.610(3) 2_656 ?
O7B C7 1.240(5) . ?
O7B Tm1 2.405(3) 2_656 ?
O11 C11 1.242(5) . ?
O14 C14 1.245(6) . ?
O17 C17 1.212(11) . ?
O21 N20 1.253(6) . ?
O22 N20 1.217(5) . ?
O23 N20 1.261(5) . ?
N11 C11 1.324(5) . ?
N11 C12 1.448(7) . ?
N11 C13 1.452(6) . ?
N14 C14 1.309(6) . ?
N14 C16 1.438(6) . ?
N14 C15 1.456(6) . ?
N17 C17 1.308(10) . ?
N17 C19 1.455(9) . ?
N17 C18 1.456(10) . ?
C1 O1 1.245(3) 2_656 ?
C1 C2 1.533(7) . ?
C2 C3 1.375(5) 2_656 ?
C2 C3 1.375(5) . ?
C3 C4 1.389(6) . ?
C4 C5 1.380(5) . ?
C5 C4 1.380(5) 2_656 ?
C5 C6 1.527(6) . ?
C6 O6 1.254(3) 2_656 ?
C7 C8 1.507(5) . ?
C7 Tm1 2.863(4) 2_656 ?
C8 C10 1.380(6) . ?
C8 C9 1.384(6) . ?
C9 C10 1.375(5) 5_666 ?
C10 C9 1.375(5) 5_666 ?
C11 H11 0.9300 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14 0.9300 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17 0.9300 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 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
O11 Tm1 O6 75.91(11) . 1_565 ?
O11 Tm1 O1 144.68(11) . . ?
O6 Tm1 O1 134.94(9) 1_565 . ?
O11 Tm1 O7A 138.68(11) . . ?
O6 Tm1 O7A 73.46(10) 1_565 . ?
O1 Tm1 O7A 75.53(9) . . ?
O11 Tm1 O14 71.19(13) . . ?
O6 Tm1 O14 143.79(11) 1_565 . ?
O1 Tm1 O14 73.96(10) . . ?
O7A Tm1 O14 142.68(11) . . ?
O11 Tm1 O7B 79.41(12) . 2_656 ?
O6 Tm1 O7B 83.02(12) 1_565 2_656 ?
O1 Tm1 O7B 87.20(11) . 2_656 ?
O7A Tm1 O7B 122.82(10) . 2_656 ?
O14 Tm1 O7B 76.54(13) . 2_656 ?
O11 Tm1 O21 102.34(14) . . ?
O6 Tm1 O21 129.25(12) 1_565 . ?
O1 Tm1 O21 72.64(12) . . ?
O7A Tm1 O21 77.28(13) . . ?
O14 Tm1 O21 73.51(14) . . ?
O7B Tm1 O21 147.46(12) 2_656 . ?
O11 Tm1 O23 72.56(13) . . ?
O6 Tm1 O23 81.52(11) 1_565 . ?
O1 Tm1 O23 121.20(11) . . ?
O7A Tm1 O23 76.06(12) . . ?
O14 Tm1 O23 102.24(14) . . ?
O7B Tm1 O23 150.52(12) 2_656 . ?
O21 Tm1 O23 51.38(11) . . ?
O11 Tm1 O7A 121.95(11) . 2_656 ?
O6 Tm1 O7A 70.45(9) 1_565 2_656 ?
O1 Tm1 O7A 69.29(9) . 2_656 ?
O7A Tm1 O7A 71.85(12) . 2_656 ?
O14 Tm1 O7A 115.52(12) . 2_656 ?
O7B Tm1 O7A 51.13(10) 2_656 2_656 ?
O21 Tm1 O7A 135.58(13) . 2_656 ?
O23 Tm1 O7A 142.06(12) . 2_656 ?
O11 Tm1 C7 100.38(12) . 2_656 ?
O6 Tm1 C7 74.58(11) 1_565 2_656 ?
O1 Tm1 C7 78.00(10) . 2_656 ?
O7A Tm1 C7 97.49(12) . 2_656 ?
O14 Tm1 C7 96.68(14) . 2_656 ?
O7B Tm1 C7 25.36(12) 2_656 2_656 ?
O21 Tm1 C7 150.56(12) . 2_656 ?
O23 Tm1 C7 156.09(12) . 2_656 ?
O7A Tm1 C7 25.80(12) 2_656 2_656 ?
O11 Tm1 N20 87.62(12) . . ?
O6 Tm1 N20 105.64(12) 1_565 . ?
O1 Tm1 N20 96.75(12) . . ?
O7A Tm1 N20 74.85(11) . . ?
O14 Tm1 N20 87.89(14) . . ?
O7B Tm1 N20 162.25(12) 2_656 . ?
O21 Tm1 N20 25.54(12) . . ?
O23 Tm1 N20 25.85(11) . . ?
O7A Tm1 N20 146.16(11) 2_656 . ?
C7 Tm1 N20 171.72(12) 2_656 . ?
C1 O1 Tm1 137.2(3) . . ?
C6 O6 Tm1 137.5(3) . 1_545 ?
C7 O7A Tm1 162.4(3) . . ?
C7 O7A Tm1 88.5(2) . 2_656 ?
Tm1 O7A Tm1 108.14(12) . 2_656 ?
C7 O7B Tm1 98.5(3) . 2_656 ?
C11 O11 Tm1 132.6(3) . . ?
C14 O14 Tm1 131.4(3) . . ?
N20 O21 Tm1 97.7(3) . . ?
N20 O23 Tm1 95.6(3) . . ?
C11 N11 C12 121.1(4) . . ?
C11 N11 C13 122.3(4) . . ?
C12 N11 C13 116.5(4) . . ?
C14 N14 C16 122.3(4) . . ?
C14 N14 C15 121.3(4) . . ?
C16 N14 C15 116.4(4) . . ?
C17 N17 C19 119.9(7) . . ?
C17 N17 C18 123.2(8) . . ?
C19 N17 C18 116.9(7) . . ?
O22 N20 O21 122.3(5) . . ?
O22 N20 O23 122.4(5) . . ?
O21 N20 O23 115.3(4) . . ?
O22 N20 Tm1 177.7(4) . . ?
O21 N20 Tm1 56.8(2) . . ?
O23 N20 Tm1 58.5(2) . . ?
O1 C1 O1 128.4(5) 2_656 . ?
O1 C1 C2 115.8(2) 2_656 . ?
O1 C1 C2 115.8(2) . . ?
C3 C2 C3 115.8(5) 2_656 . ?
C3 C2 C1 122.1(2) 2_656 . ?
C3 C2 C1 122.1(2) . . ?
F3 C3 C2 120.1(4) . . ?
F3 C3 C4 117.4(4) . . ?
C2 C3 C4 122.6(4) . . ?
F4 C4 C5 120.8(4) . . ?
F4 C4 C3 118.0(4) . . ?
C5 C4 C3 121.2(4) . . ?
C4 C5 C4 116.7(5) 2_656 . ?
C4 C5 C6 121.7(2) 2_656 . ?
C4 C5 C6 121.7(2) . . ?
O6 C6 O6 128.7(5) 2_656 . ?
O6 C6 C5 115.6(2) 2_656 . ?
O6 C6 C5 115.6(2) . . ?
O7B C7 O7A 121.8(4) . . ?
O7B C7 C8 119.0(4) . . ?
O7A C7 C8 119.2(4) . . ?
O7B C7 Tm1 56.2(2) . 2_656 ?
O7A C7 Tm1 65.7(2) . 2_656 ?
C8 C7 Tm1 174.8(3) . 2_656 ?
C10 C8 C9 116.6(3) . . ?
C10 C8 C7 121.6(4) . . ?
C9 C8 C7 121.7(4) . . ?
F9 C9 C10 119.3(4) . 5_666 ?
F9 C9 C8 119.3(3) . . ?
C10 C9 C8 121.3(4) 5_666 . ?
F10 C10 C9 118.5(4) . 5_666 ?
F10 C10 C8 119.4(3) . . ?
C9 C10 C8 122.0(4) 5_666 . ?
O11 C11 N11 123.2(4) . . ?
O11 C11 H11 118.4 . . ?
N11 C11 H11 118.4 . . ?
N11 C12 H12A 109.5 . . ?
N11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
N11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N11 C13 H13A 109.5 . . ?
N11 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
N11 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O14 C14 N14 123.4(4) . . ?
O14 C14 H14 118.3 . . ?
N14 C14 H14 118.3 . . ?
N14 C15 H15A 109.5 . . ?
N14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
N14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N14 C16 H16A 109.5 . . ?
N14 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
N14 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O17 C17 N17 126.7(9) . . ?
O17 C17 H17 116.6 . . ?
N17 C17 H17 116.6 . . ?
N17 C18 H18A 109.5 . . ?
N17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
N17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
N17 C19 H19A 109.5 . . ?
N17 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
N17 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 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






O11 Tm1 O1 C1 -166.8(2) . . . . ?
O6 Tm1 O1 C1 -22.3(4) 1_565 . . . ?
O7A Tm1 O1 C1 25.4(3) . . . . ?
O14 Tm1 O1 C1 -176.4(3) . . . . ?
O7B Tm1 O1 C1 -99.6(3) 2_656 . . . ?
O21 Tm1 O1 C1 106.3(3) . . . . ?
O23 Tm1 O1 C1 88.8(3) . . . . ?
O7A Tm1 O1 C1 -50.4(3) 2_656 . . . ?
C7 Tm1 O1 C1 -75.7(3) 2_656 . . . ?
N20 Tm1 O1 C1 97.8(3) . . . . ?
O11 Tm1 O7A C7 -41.7(9) . . . . ?
O6 Tm1 O7A C7 -85.5(9) 1_565 . . . ?
O1 Tm1 O7A C7 127.6(9) . . . . ?
O14 Tm1 O7A C7 91.7(9) . . . . ?
O7B Tm1 O7A C7 -155.4(9) 2_656 . . . ?
O21 Tm1 O7A C7 52.6(9) . . . . ?
O23 Tm1 O7A C7 -0.3(9) . . . . ?
O7A Tm1 O7A C7 -159.8(9) 2_656 . . . ?
C7 Tm1 O7A C7 -156.9(9) 2_656 . . . ?
N20 Tm1 O7A C7 26.4(9) . . . . ?
O11 Tm1 O7A Tm1 118.91(16) . . . 2_656 ?
O6 Tm1 O7A Tm1 75.17(11) 1_565 . . 2_656 ?
O1 Tm1 O7A Tm1 -71.72(10) . . . 2_656 ?
O14 Tm1 O7A Tm1 -107.71(19) . . . 2_656 ?
O7B Tm1 O7A Tm1 5.19(16) 2_656 . . 2_656 ?
O21 Tm1 O7A Tm1 -146.79(13) . . . 2_656 ?
O23 Tm1 O7A Tm1 160.31(13) . . . 2_656 ?
O7A Tm1 O7A Tm1 0.83(12) 2_656 . . 2_656 ?
C7 Tm1 O7A Tm1 3.76(12) 2_656 . . 2_656 ?
N20 Tm1 O7A Tm1 -173.00(14) . . . 2_656 ?
O6 Tm1 O11 C11 58.0(4) 1_565 . . . ?
O1 Tm1 O11 C11 -147.1(4) . . . . ?
O7A Tm1 O11 C11 14.9(5) . . . . ?
O14 Tm1 O11 C11 -137.4(4) . . . . ?
O7B Tm1 O11 C11 143.4(4) 2_656 . . . ?
O21 Tm1 O11 C11 -69.8(4) . . . . ?
O23 Tm1 O11 C11 -27.4(4) . . . . ?
O7A Tm1 O11 C11 113.7(4) 2_656 . . . ?
C7 Tm1 O11 C11 129.0(4) 2_656 . . . ?
N20 Tm1 O11 C11 -48.8(4) . . . . ?
O11 Tm1 O14 C14 166.2(5) . . . . ?
O6 Tm1 O14 C14 -168.0(4) 1_565 . . . ?
O1 Tm1 O14 C14 -19.7(5) . . . . ?
O7A Tm1 O14 C14 16.6(6) . . . . ?
O7B Tm1 O14 C14 -110.6(5) 2_656 . . . ?
O21 Tm1 O14 C14 56.5(5) . . . . ?
O23 Tm1 O14 C14 99.6(5) . . . . ?
O7A Tm1 O14 C14 -76.6(5) 2_656 . . . ?
C7 Tm1 O14 C14 -95.1(5) 2_656 . . . ?
N20 Tm1 O14 C14 78.0(5) . . . . ?
O11 Tm1 O21 N20 56.2(3) . . . . ?
O6 Tm1 O21 N20 -25.6(4) 1_565 . . . ?
O1 Tm1 O21 N20 -160.0(3) . . . . ?
O7A Tm1 O21 N20 -81.4(3) . . . . ?
O14 Tm1 O21 N20 122.1(3) . . . . ?
O7B Tm1 O21 N20 145.8(3) 2_656 . . . ?
O23 Tm1 O21 N20 0.8(3) . . . . ?
O7A Tm1 O21 N20 -128.1(3) 2_656 . . . ?
C7 Tm1 O21 N20 -164.1(3) 2_656 . . . ?
O11 Tm1 O23 N20 -123.3(3) . . . . ?
O6 Tm1 O23 N20 158.9(3) 1_565 . . . ?
O1 Tm1 O23 N20 20.8(3) . . . . ?
O7A Tm1 O23 N20 84.0(3) . . . . ?
O14 Tm1 O23 N20 -57.7(3) . . . . ?
O7B Tm1 O23 N20 -142.0(3) 2_656 . . . ?
O21 Tm1 O23 N20 -0.7(3) . . . . ?
O7A Tm1 O23 N20 116.8(3) 2_656 . . . ?
C7 Tm1 O23 N20 160.8(3) 2_656 . . . ?
Tm1 O21 N20 O22 177.6(4) . . . . ?
Tm1 O21 N20 O23 -1.3(5) . . . . ?
Tm1 O23 N20 O22 -177.6(4) . . . . ?
Tm1 O23 N20 O21 1.3(5) . . . . ?
O11 Tm1 N20 O21 -125.7(3) . . . . ?
O6 Tm1 N20 O21 159.7(3) 1_565 . . . ?
O1 Tm1 N20 O21 19.2(3) . . . . ?
O7A Tm1 N20 O21 92.1(3) . . . . ?
O14 Tm1 N20 O21 -54.4(3) . . . . ?
O7B Tm1 N20 O21 -82.9(5) 2_656 . . . ?
O23 Tm1 N20 O21 -178.6(5) . . . . ?
O7A Tm1 N20 O21 81.6(4) 2_656 . . . ?
O11 Tm1 N20 O23 53.0(3) . . . . ?
O6 Tm1 N20 O23 -21.7(3) 1_565 . . . ?
O1 Tm1 N20 O23 -162.2(3) . . . . ?
O7A Tm1 N20 O23 -89.2(3) . . . . ?
O14 Tm1 N20 O23 124.2(3) . . . . ?
O7B Tm1 N20 O23 95.8(5) 2_656 . . . ?
O21 Tm1 N20 O23 178.6(5) . . . . ?
O7A Tm1 N20 O23 -99.8(3) 2_656 . . . ?
Tm1 O1 C1 O1 10.86(19) . . . 2_656 ?
Tm1 O1 C1 C2 -169.14(19) . . . . ?
O1 C1 C2 C3 -47.1(3) 2_656 . . 2_656 ?
O1 C1 C2 C3 132.9(3) . . . 2_656 ?
O1 C1 C2 C3 132.9(3) 2_656 . . . ?
O1 C1 C2 C3 -47.1(3) . . . . ?
C3 C2 C3 F3 177.7(5) 2_656 . . . ?
C1 C2 C3 F3 -2.3(5) . . . . ?
C3 C2 C3 C4 -0.6(3) 2_656 . . . ?
C1 C2 C3 C4 179.4(3) . . . . ?
F3 C3 C4 F4 0.8(6) . . . . ?
C2 C3 C4 F4 179.1(4) . . . . ?
F3 C3 C4 C5 -177.1(4) . . . . ?
C2 C3 C4 C5 1.2(6) . . . . ?
F4 C4 C5 C4 -178.4(5) . . . 2_656 ?
C3 C4 C5 C4 -0.6(3) . . . 2_656 ?
F4 C4 C5 C6 1.6(5) . . . . ?
C3 C4 C5 C6 179.4(3) . . . . ?
Tm1 O6 C6 O6 -4.1(2) 1_545 . . 2_656 ?
Tm1 O6 C6 C5 175.9(2) 1_545 . . . ?
C4 C5 C6 O6 51.9(3) 2_656 . . 2_656 ?
C4 C5 C6 O6 -128.1(3) . . . 2_656 ?
C4 C5 C6 O6 -128.1(3) 2_656 . . . ?
C4 C5 C6 O6 51.9(3) . . . . ?
Tm1 O7B C7 O7A -3.9(4) 2_656 . . . ?
Tm1 O7B C7 C8 177.6(3) 2_656 . . . ?
Tm1 O7A C7 O7B 165.2(6) . . . . ?
Tm1 O7A C7 O7B 3.5(4) 2_656 . . . ?
Tm1 O7A C7 C8 -16.3(11) . . . . ?
Tm1 O7A C7 C8 -178.0(3) 2_656 . . . ?
Tm1 O7A C7 Tm1 161.6(9) . . . 2_656 ?
O7B C7 C8 C10 78.5(5) . . . . ?
O7A C7 C8 C10 -100.1(5) . . . . ?
O7B C7 C8 C9 -102.1(5) . . . . ?
O7A C7 C8 C9 79.3(5) . . . . ?
C10 C8 C9 F9 -178.9(4) . . . . ?
C7 C8 C9 F9 1.7(6) . . . . ?
C10 C8 C9 C10 -0.5(7) . . . 5_666 ?
C7 C8 C9 C10 -179.9(4) . . . 5_666 ?
C9 C8 C10 F10 -179.5(3) . . . . ?
C7 C8 C10 F10 0.0(6) . . . . ?
C9 C8 C10 C9 0.5(7) . . . 5_666 ?
C7 C8 C10 C9 179.9(4) . . . 5_666 ?
Tm1 O11 C11 N11 158.1(3) . . . . ?
C12 N11 C11 O11 0.2(7) . . . . ?
C13 N11 C11 O11 -177.2(5) . . . . ?
Tm1 O14 C14 N14 176.7(3) . . . . ?
C16 N14 C14 O14 2.7(8) . . . . ?
C15 N14 C14 O14 -178.4(5) . . . . ?
C19 N17 C17 O17 -2.6(14) . . . . ?
C18 N17 C17 O17 174.4(10) . . . . ?

_diffrn_measured_fraction_theta_max 0.741
_diffrn_reflns_theta_full        27.22
_diffrn_measured_fraction_theta_full 0.741
_refine_diff_density_max         1.395
_refine_diff_density_min         -1.412
_refine_diff_density_rms         0.130
####################################################################### 
# 
# 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_shelxl
_database_code_depnum_ccdc_archive 'CCDC 1025456'
_audit_update_record             
;
2014-09-19 deposited with the CCDC.
2015-02-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H21 F4 N6 O12 Sm'
_chemical_formula_weight         715.74

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'
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                   10.9816(13)
_cell_length_b                   11.1645(13)
_cell_length_c                   11.5291(12)
_cell_angle_alpha                101.818(9)
_cell_angle_beta                 104.289(9)
_cell_angle_gamma                101.705(9)
_cell_volume                     1292.0(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      2.29
_cell_measurement_theta_max      59.53

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.840
_exptl_crystal_F_000             706
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_exptl_absorpt_coefficient_mu    2.370
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.6433
_exptl_absorpt_correction_T_max  0.7110
_exptl_absorpt_process_details   'STOE XRed, XShape'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'STOE IPDS II'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            25552
_diffrn_reflns_av_unetI/netI     0.0727
_diffrn_reflns_av_R_equivalents  0.0876
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.892
_diffrn_reflns_theta_max         29.531
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             7176
_reflns_number_gt                5383
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0163P)²+2.8733P] 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         7176
_refine_ls_number_parameters     353
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0789
_refine_ls_R_factor_gt           0.0457
_refine_ls_wR_factor_ref         0.0863
_refine_ls_wR_factor_gt          0.0752
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_restrained_S_all      1.084
_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 0.11101(3) 0.37395(3) 0.50180(2) 0.02401(7) Uani 1 1 d . . . . .
F7 F 0.3124(4) 0.2838(4) 0.9600(3) 0.0590(10) Uani 1 1 d . . . . .
C4 C -0.1095(5) 0.4630(6) 0.0332(5) 0.0390(12) Uani 1 1 d . . . . .
O12B O -0.1226(3) 0.4045(3) 0.4383(3) 0.0322(7) Uani 1 1 d . . . . .
F8 F 0.5569(4) 0.5807(4) 0.8080(3) 0.0556(9) Uani 1 1 d . . . . .
F4 F -0.2195(3) 0.4212(4) 0.0614(3) 0.0672(12) Uani 1 1 d . . . . .
O9 O 0.0637(4) 0.1726(3) 0.5584(3) 0.0437(9) Uani 1 1 d . . . . .
O1 O 0.0686(3) 0.4322(3) 0.3022(3) 0.0330(7) Uani 1 1 d . . . . .
O11 O 0.3225(3) 0.4838(3) 0.4759(3) 0.0386(8) Uani 1 1 d . . . . .
O5A O 0.2918(4) 0.3993(4) 0.6755(3) 0.0453(9) Uani 1 1 d . . . . .
O12A O -0.0990(4) 0.2228(3) 0.3487(3) 0.0411(9) Uani 1 1 d . . . . .
O10 O 0.1753(4) 0.2177(4) 0.3647(4) 0.0441(9) Uani 1 1 d . . . . .
F3 F 0.2353(3) 0.5891(5) 0.1752(3) 0.0727(13) Uani 1 1 d . . . . .
O2 O 0.0322(4) 0.4124(4) 0.6853(3) 0.0438(9) Uani 1 1 d . . . . .
C1 C 0.0157(5) 0.5109(4) 0.2599(4) 0.0276(9) Uani 1 1 d . . . . .
O5B O 0.3727(4) 0.2396(4) 0.7151(4) 0.0545(11) Uani 1 1 d . . . . .
C14 C 0.0052(8) 0.8263(7) 0.9943(7) 0.070(2) Uani 1 1 d . . . . .
H14 H -0.0769 0.7688 0.9621 0.084 Uiso 1 1 calc R U . . .
C2 C 0.0079(5) 0.5074(5) 0.1259(4) 0.0301(10) Uani 1 1 d . . . . .
O15 O 0.3556(6) 0.9789(6) 0.0450(6) 0.092(2) Uani 1 1 d . . . . .
C6 C 0.4314(5) 0.4268(5) 0.8757(4) 0.0355(11) Uani 1 1 d . . . . .
C3 C 0.1171(5) 0.5438(6) 0.0897(4) 0.0394(12) Uani 1 1 d . . . . .
N11 N 0.4619(4) 0.6381(5) 0.4379(5) 0.0463(11) Uani 1 1 d . . . . .
H3A H 0.5254 0.6039 0.4535 0.056 Uiso 1 1 calc R U . . .
H3B H 0.4730 0.7081 0.4167 0.056 Uiso 1 1 calc R U . . .
C7 C 0.4067(5) 0.3907(5) 0.9781(5) 0.0398(12) Uani 1 1 d . . . . .
C12 C -0.1686(5) 0.2970(5) 0.3583(4) 0.0316(10) Uani 1 1 d . . . . .
N9 N 0.0488(6) 0.0417(5) 0.6829(5) 0.0575(14) Uani 1 1 d . . . . .
H1A H 0.0352 -0.0251 0.6237 0.069 Uiso 1 1 calc R U . . .
H1B H 0.0514 0.0351 0.7564 0.069 Uiso 1 1 calc R U . . .
N16 N 0.3047(14) 0.0113(9) 0.5107(9) 0.164(5) Uani 1 1 d . . . . .
H40A H 0.3758 0.0545 0.5677 0.197 Uiso 1 1 calc R U . . .
H40B H 0.2337 0.0334 0.5084 0.197 Uiso 1 1 calc R U . . .
C10 C 0.2506(7) 0.2170(7) 0.3016(6) 0.0550(16) Uani 1 1 d . . . . .
H10 H 0.3156 0.2917 0.3187 0.066 Uiso 1 1 calc R U . . .
C8 C 0.5261(5) 0.5394(5) 0.9028(5) 0.0374(11) Uani 1 1 d . . . . .
C5 C 0.3585(5) 0.3472(5) 0.7442(5) 0.0362(11) Uani 1 1 d . . . . .
N14 N 0.0767(7) 0.8371(6) 0.9201(5) 0.0755(19) Uani 1 1 d . . . . .
H12A H 0.1530 0.8895 0.9471 0.091 Uiso 1 1 calc R U . . .
H12B H 0.0475 0.7919 0.8441 0.091 Uiso 1 1 calc R U . . .
C9 C 0.0655(5) 0.1525(5) 0.6611(5) 0.0388(12) Uani 1 1 d . . . . .
H9 H 0.0799 0.2224 0.7275 0.047 Uiso 1 1 calc R U . . .
O14 O 0.0383(7) 0.8857(6) 1.1013(5) 0.0950(19) Uani 1 1 d . . . . .
C11 C 0.3487(5) 0.5838(5) 0.4464(4) 0.0345(11) Uani 1 1 d . . . . .
H11 H 0.2824 0.6237 0.4288 0.041 Uiso 1 1 calc R U . . .
N10 N 0.2484(7) 0.1246(7) 0.2154(6) 0.0793(19) Uani 1 1 d . . . . .
H2A H 0.1900 0.0537 0.1964 0.095 Uiso 1 1 calc R U . . .
H2B H 0.3054 0.1328 0.1760 0.095 Uiso 1 1 calc R U . . .
C13 C -0.3074(6) 0.2618(6) 0.2752(6) 0.0558(16) Uani 1 1 d . . . . .
H13A H -0.3461 0.3300 0.2953 0.084 Uiso 1 1 calc R U . . .
H13B H -0.3563 0.1863 0.2875 0.084 Uiso 1 1 calc R U . . .
H13C H -0.3081 0.2467 0.1900 0.084 Uiso 1 1 calc R U . . .
N15 N 0.5178(7) 0.8975(7) 0.1147(6) 0.083(2) Uani 1 1 d . . . . .
H9A H 0.5647 0.9304 0.0737 0.099 Uiso 1 1 calc R U . . .
H9B H 0.5464 0.8517 0.1611 0.099 Uiso 1 1 calc R U . . .
O16 O 0.3628(8) -0.1393(7) 0.4014(9) 0.133(3) Uani 1 1 d . . . . .
C16 C 0.3044(16) -0.0756(14) 0.4377(16) 0.146(6) Uani 1 1 d . . . . .
H039 H 0.2192 -0.1082 0.3854 0.175 Uiso 1 1 calc R U . . .
C15 C 0.4087(10) 0.9160(9) 0.1071(9) 0.087(3) Uani 1 1 d . . . . .
H044 H 0.3621 0.8782 0.1534 0.105 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 O5A 2.368(3) . ?
Sm1 O12B 2.396(3) 2_566 ?
Sm1 O10 2.441(4) . ?
Sm1 O9 2.458(4) . ?
Sm1 O2 2.469(3) . ?
Sm1 O1 2.478(3) . ?
Sm1 O11 2.515(4) . ?
Sm1 O12A 2.544(4) . ?
Sm1 O12B 2.601(3) . ?
Sm1 C12 2.957(5) . ?
Sm1 Sm1 4.0805(7) 2_566 ?
F7 C7 1.353(6) . ?
C4 F4 1.345(6) . ?
C4 C2 1.376(7) . ?
C4 C3 1.384(7) 2_565 ?
O12B C12 1.272(6) . ?
O12B Sm1 2.396(3) 2_566 ?
F8 C8 1.359(6) . ?
O9 C9 1.247(6) . ?
O1 C1 1.260(5) . ?
O11 C11 1.232(6) . ?
O5A C5 1.256(6) . ?
O12A C12 1.243(6) . ?
O10 C10 1.228(7) . ?
F3 C3 1.346(6) . ?
O2 C1 1.239(6) 2_566 ?
C1 O2 1.239(6) 2_566 ?
C1 C2 1.518(6) . ?
O5B C5 1.232(7) . ?
C14 O14 1.200(9) . ?
C14 N14 1.302(10) . ?
C14 H14 0.9300 . ?
C2 C3 1.377(7) . ?
O15 C15 1.229(10) . ?
C6 C8 1.381(7) . ?
C6 C7 1.392(7) . ?
C6 C5 1.513(7) . ?
C3 C4 1.384(7) 2_565 ?
N11 C11 1.305(6) . ?
N11 H3A 0.8600 . ?
N11 H3B 0.8600 . ?
C7 C8 1.366(7) 2_667 ?
C12 C13 1.509(7) . ?
N9 C9 1.298(6) . ?
N9 H1A 0.8600 . ?
N9 H1B 0.8600 . ?
N16 C16 1.146(15) . ?
N16 H40A 0.8600 . ?
N16 H40B 0.8600 . ?
C10 N10 1.270(8) . ?
C10 H10 0.9300 . ?
C8 C7 1.366(7) 2_667 ?
N14 H12A 0.8600 . ?
N14 H12B 0.8600 . ?
C9 H9 0.9300 . ?
C11 H11 0.9300 . ?
N10 H2A 0.8600 . ?
N10 H2B 0.8600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
N15 C15 1.242(10) . ?
N15 H9A 0.8600 . ?
N15 H9B 0.8600 . ?
O16 C16 1.133(13) . ?
C16 H039 0.9300 . ?
C15 H044 0.9300 . ?

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
O5A Sm1 O12B 91.24(12) . 2_566 ?
O5A Sm1 O10 93.59(14) . . ?
O12B Sm1 O10 142.61(12) 2_566 . ?
O5A Sm1 O9 76.15(13) . . ?
O12B Sm1 O9 144.61(12) 2_566 . ?
O10 Sm1 O9 72.06(13) . . ?
O5A Sm1 O2 74.04(13) . . ?
O12B Sm1 O2 72.44(12) 2_566 . ?
O10 Sm1 O2 144.14(12) . . ?
O9 Sm1 O2 72.31(12) . . ?
O5A Sm1 O1 137.95(13) . . ?
O12B Sm1 O1 76.34(11) 2_566 . ?
O10 Sm1 O1 75.40(12) . . ?
O9 Sm1 O1 134.00(12) . . ?
O2 Sm1 O1 135.46(11) . . ?
O5A Sm1 O11 67.85(13) . . ?
O12B Sm1 O11 75.42(12) 2_566 . ?
O10 Sm1 O11 72.28(13) . . ?
O9 Sm1 O11 126.58(13) . . ?
O2 Sm1 O11 128.76(13) . . ?
O1 Sm1 O11 70.15(11) . . ?
O5A Sm1 O12A 145.72(12) . . ?
O12B Sm1 O12A 118.47(11) 2_566 . ?
O10 Sm1 O12A 73.53(13) . . ?
O9 Sm1 O12A 69.70(12) . . ?
O2 Sm1 O12A 97.71(14) . . ?
O1 Sm1 O12A 70.47(12) . . ?
O11 Sm1 O12A 132.81(12) . . ?
O5A Sm1 O12B 143.08(12) . . ?
O12B Sm1 O12B 70.57(12) 2_566 . ?
O10 Sm1 O12B 120.58(12) . . ?
O9 Sm1 O12B 99.98(12) . . ?
O2 Sm1 O12B 69.94(11) . . ?
O1 Sm1 O12B 70.15(11) . . ?
O11 Sm1 O12B 132.38(11) . . ?
O12A Sm1 O12B 50.04(11) . . ?
O5A Sm1 C12 155.12(13) . . ?
O12B Sm1 C12 94.55(12) 2_566 . ?
O10 Sm1 C12 96.34(14) . . ?
O9 Sm1 C12 85.31(13) . . ?
O2 Sm1 C12 84.70(13) . . ?
O1 Sm1 C12 66.85(12) . . ?
O11 Sm1 C12 136.99(12) . . ?
O12A Sm1 C12 24.67(12) . . ?
O12B Sm1 C12 25.43(12) . . ?
O5A Sm1 Sm1 121.49(10) . 2_566 ?
O12B Sm1 Sm1 36.95(8) 2_566 2_566 ?
O10 Sm1 Sm1 142.26(9) . 2_566 ?
O9 Sm1 Sm1 126.09(10) . 2_566 ?
O2 Sm1 Sm1 66.69(8) . 2_566 ?
O1 Sm1 Sm1 69.20(8) . 2_566 ?
O11 Sm1 Sm1 106.37(8) . 2_566 ?
O12A Sm1 Sm1 82.56(8) . 2_566 ?
O12B Sm1 Sm1 33.62(7) . 2_566 ?
C12 Sm1 Sm1 58.05(10) . 2_566 ?
F4 C4 C2 119.6(4) . . ?
F4 C4 C3 118.8(5) . 2_565 ?
C2 C4 C3 121.6(5) . 2_565 ?
C12 O12B Sm1 149.8(3) . 2_566 ?
C12 O12B Sm1 93.1(3) . . ?
Sm1 O12B Sm1 109.43(12) 2_566 . ?
C9 O9 Sm1 130.2(3) . . ?
C1 O1 Sm1 135.2(3) . . ?
C11 O11 Sm1 128.0(3) . . ?
C5 O5A Sm1 147.6(4) . . ?
C12 O12A Sm1 96.6(3) . . ?
C10 O10 Sm1 138.0(4) . . ?
C1 O2 Sm1 139.8(3) 2_566 . ?
O2 C1 O1 127.2(4) 2_566 . ?
O2 C1 C2 117.3(4) 2_566 . ?
O1 C1 C2 115.5(4) . . ?
O14 C14 N14 124.3(8) . . ?
O14 C14 H14 117.8 . . ?
N14 C14 H14 117.8 . . ?
C4 C2 C3 116.5(4) . . ?
C4 C2 C1 121.2(4) . . ?
C3 C2 C1 122.3(4) . . ?
C8 C6 C7 115.5(5) . . ?
C8 C6 C5 122.8(5) . . ?
C7 C6 C5 121.7(5) . . ?
F3 C3 C2 119.9(4) . . ?
F3 C3 C4 118.2(5) . 2_565 ?
C2 C3 C4 121.9(5) . 2_565 ?
C11 N11 H3A 120.0 . . ?
C11 N11 H3B 120.0 . . ?
H3A N11 H3B 120.0 . . ?
F7 C7 C8 118.5(5) . 2_667 ?
F7 C7 C6 119.4(5) . . ?
C8 C7 C6 122.1(5) 2_667 . ?
O12A C12 O12B 119.9(4) . . ?
O12A C12 C13 120.9(5) . . ?
O12B C12 C13 119.2(5) . . ?
O12A C12 Sm1 58.7(3) . . ?
O12B C12 Sm1 61.4(2) . . ?
C13 C12 Sm1 174.5(4) . . ?
C9 N9 H1A 120.0 . . ?
C9 N9 H1B 120.0 . . ?
H1A N9 H1B 120.0 . . ?
C16 N16 H40A 120.0 . . ?
C16 N16 H40B 120.0 . . ?
H40A N16 H40B 120.0 . . ?
O10 C10 N10 126.5(7) . . ?
O10 C10 H10 116.8 . . ?
N10 C10 H10 116.8 . . ?
F8 C8 C7 118.4(5) . 2_667 ?
F8 C8 C6 119.1(5) . . ?
C7 C8 C6 122.4(5) 2_667 . ?
O5B C5 O5A 126.9(5) . . ?
O5B C5 C6 116.9(4) . . ?
O5A C5 C6 116.2(5) . . ?
C14 N14 H12A 120.0 . . ?
C14 N14 H12B 120.0 . . ?
H12A N14 H12B 120.0 . . ?
O9 C9 N9 125.2(5) . . ?
O9 C9 H9 117.4 . . ?
N9 C9 H9 117.4 . . ?
O11 C11 N11 125.2(5) . . ?
O11 C11 H11 117.4 . . ?
N11 C11 H11 117.4 . . ?
C10 N10 H2A 120.0 . . ?
C10 N10 H2B 120.0 . . ?
H2A N10 H2B 120.0 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C15 N15 H9A 120.0 . . ?
C15 N15 H9B 120.0 . . ?
H9A N15 H9B 120.0 . . ?
O16 C16 N16 147(2) . . ?
O16 C16 H039 106.4 . . ?
N16 C16 H039 106.4 . . ?
O15 C15 N15 127.1(9) . . ?
O15 C15 H044 116.5 . . ?
N15 C15 H044 116.5 . . ?

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
Sm1 O1 C1 O2 0.9(8) . . . 2_566 ?
Sm1 O1 C1 C2 -177.5(3) . . . . ?
F4 C4 C2 C3 177.4(5) . . . . ?
C3 C4 C2 C3 -0.5(9) 2_565 . . . ?
F4 C4 C2 C1 -0.3(8) . . . . ?
C3 C4 C2 C1 -178.2(5) 2_565 . . . ?
O2 C1 C2 C4 -68.8(7) 2_566 . . . ?
O1 C1 C2 C4 109.8(6) . . . . ?
O2 C1 C2 C3 113.6(6) 2_566 . . . ?
O1 C1 C2 C3 -67.8(7) . . . . ?
C4 C2 C3 F3 179.5(5) . . . . ?
C1 C2 C3 F3 -2.8(8) . . . . ?
C4 C2 C3 C4 0.5(9) . . . 2_565 ?
C1 C2 C3 C4 178.2(5) . . . 2_565 ?
C8 C6 C7 F7 177.8(5) . . . . ?
C5 C6 C7 F7 -2.0(8) . . . . ?
C8 C6 C7 C8 -1.6(9) . . . 2_667 ?
C5 C6 C7 C8 178.6(5) . . . 2_667 ?
Sm1 O12A C12 O12B -5.8(5) . . . . ?
Sm1 O12A C12 C13 173.6(5) . . . . ?
Sm1 O12B C12 O12A 144.8(5) 2_566 . . . ?
Sm1 O12B C12 O12A 5.6(5) . . . . ?
Sm1 O12B C12 C13 -34.6(9) 2_566 . . . ?
Sm1 O12B C12 C13 -173.8(4) . . . . ?
Sm1 O12B C12 Sm1 139.2(6) 2_566 . . . ?
Sm1 O10 C10 N10 -163.5(5) . . . . ?
C7 C6 C8 F8 179.4(5) . . . . ?
C5 C6 C8 F8 -0.8(8) . . . . ?
C7 C6 C8 C7 1.6(9) . . . 2_667 ?
C5 C6 C8 C7 -178.6(5) . . . 2_667 ?
Sm1 O5A C5 O5B 27.8(11) . . . . ?
Sm1 O5A C5 C6 -153.7(5) . . . . ?
C8 C6 C5 O5B 117.3(6) . . . . ?
C7 C6 C5 O5B -62.8(7) . . . . ?
C8 C6 C5 O5A -61.2(7) . . . . ?
C7 C6 C5 O5A 118.6(6) . . . . ?
Sm1 O9 C9 N9 -174.1(4) . . . . ?
Sm1 O11 C11 N11 177.9(4) . . . . ?

_refine_diff_density_max         1.020
_refine_diff_density_min         -2.065
_refine_diff_density_rms         0.172

_shelxl_version_number           2013-4


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: formamide'
####################################################################### 
# 
# 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_shelxl
_database_code_depnum_ccdc_archive 'CCDC 1025457'
_audit_update_record             
;
2014-09-19 deposited with the CCDC.
2015-02-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H21 Eu F4 N6 O12'
_chemical_formula_weight         717.35

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'
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                   10.9465(5)
_cell_length_b                   11.1155(5)
_cell_length_c                   11.4684(5)
_cell_angle_alpha                101.707(3)
_cell_angle_beta                 104.300(3)
_cell_angle_gamma                101.651(3)
_cell_volume                     1276.49(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      2.29
_cell_measurement_theta_max      59.53

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.866
_exptl_crystal_F_000             708
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_absorpt_coefficient_mu    2.556
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.4428
_exptl_absorpt_correction_T_max  0.7079
_exptl_absorpt_process_details   'STOE XRed, XShape'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'STOE IPDS II'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20469
_diffrn_reflns_av_unetI/netI     0.0265
_diffrn_reflns_av_R_equivalents  0.0366
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.901
_diffrn_reflns_theta_max         29.176
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             6852
_reflns_number_gt                6422
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0305P)²+1.0098P] 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     SHELXL
_refine_ls_extinction_coef       0.0044(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         6852
_refine_ls_number_parameters     353
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0256
_refine_ls_R_factor_gt           0.0233
_refine_ls_wR_factor_ref         0.0599
_refine_ls_wR_factor_gt          0.0577
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_restrained_S_all      1.072
_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 0.11058(2) 0.37382(2) 0.50172(2) 0.02143(5) Uani 1 1 d . . . . .
F7 F 0.3113(2) 0.28418(19) 0.95964(17) 0.0540(5) Uani 1 1 d . . . . .
C4 C -0.1095(3) 0.4629(3) 0.0337(2) 0.0344(5) Uani 1 1 d . . . . .
O12B O -0.12259(16) 0.40590(16) 0.43824(15) 0.0291(3) Uani 1 1 d . . . . .
F8 F 0.55595(19) 0.58116(19) 0.80767(15) 0.0504(5) Uani 1 1 d . . . . .
F4 F -0.21916(18) 0.4211(3) 0.06260(17) 0.0610(6) Uani 1 1 d . . . . .
O9 O 0.0643(2) 0.17207(18) 0.55840(17) 0.0398(4) Uani 1 1 d . . . . .
O1 O 0.06855(17) 0.43202(17) 0.30261(15) 0.0300(3) Uani 1 1 d . . . . .
O11 O 0.32207(18) 0.48303(18) 0.47585(18) 0.0356(4) Uani 1 1 d . . . . .
O5A O 0.2906(2) 0.3999(2) 0.67593(18) 0.0412(4) Uani 1 1 d . . . . .
O12A O -0.09874(19) 0.22293(18) 0.34986(19) 0.0390(4) Uani 1 1 d . . . . .
O10 O 0.1741(2) 0.21804(19) 0.36506(19) 0.0397(4) Uani 1 1 d . . . . .
F3 F 0.23600(18) 0.5897(3) 0.17524(17) 0.0668(7) Uani 1 1 d . . . . .
O2 O 0.0300(2) 0.41011(19) 0.68446(17) 0.0402(4) Uani 1 1 d . . . . .
C1 C 0.0166(2) 0.5105(2) 0.2614(2) 0.0270(4) Uani 1 1 d . . . . .
O5B O 0.3730(2) 0.2404(2) 0.7137(2) 0.0495(5) Uani 1 1 d . . . . .
C14 C 0.0047(4) 0.8260(4) 0.9929(4) 0.0628(9) Uani 1 1 d . . . . .
H14 H -0.0780 0.7690 0.9610 0.075 Uiso 1 1 calc R U . . .
C2 C 0.0089(2) 0.5076(2) 0.1261(2) 0.0284(4) Uani 1 1 d . . . . .
O15 O 0.3542(3) 0.9772(4) 0.0436(4) 0.0841(10) Uani 1 1 d . . . . .
C6 C 0.4306(2) 0.4275(3) 0.8766(2) 0.0315(5) Uani 1 1 d . . . . .
C3 C 0.1181(3) 0.5445(3) 0.0899(2) 0.0351(5) Uani 1 1 d . . . . .
N11 N 0.4617(2) 0.6369(3) 0.4369(3) 0.0435(5) Uani 1 1 d . . . . .
H3A H 0.5248 0.6017 0.4527 0.052 Uiso 1 1 calc R U . . .
H3B H 0.4738 0.7071 0.4154 0.052 Uiso 1 1 calc R U . . .
C7 C 0.4065(3) 0.3902(3) 0.9777(2) 0.0354(5) Uani 1 1 d . . . . .
C12 C -0.1691(2) 0.2972(2) 0.3586(2) 0.0289(4) Uani 1 1 d . . . . .
N9 N 0.0504(3) 0.0417(2) 0.6832(3) 0.0506(7) Uani 1 1 d . . . . .
H1A H 0.0367 -0.0254 0.6239 0.061 Uiso 1 1 calc R U . . .
H1B H 0.0534 0.0351 0.7572 0.061 Uiso 1 1 calc R U . . .
N16 N 0.3076(9) 0.0128(6) 0.5088(6) 0.156(3) Uani 1 1 d . . . . .
H40A H 0.3816 0.0587 0.5602 0.187 Uiso 1 1 calc R U . . .
H40B H 0.2371 0.0345 0.5116 0.187 Uiso 1 1 calc R U . . .
C10 C 0.2513(3) 0.2186(3) 0.3033(3) 0.0477(7) Uani 1 1 d . . . . .
H10 H 0.3170 0.2932 0.3212 0.057 Uiso 1 1 calc R U . . .
C8 C 0.5261(3) 0.5392(3) 0.9019(2) 0.0344(5) Uani 1 1 d . . . . .
C5 C 0.3577(2) 0.3473(3) 0.7433(2) 0.0330(5) Uani 1 1 d . . . . .
N14 N 0.0742(4) 0.8348(4) 0.9184(3) 0.0659(9) Uani 1 1 d . . . . .
H12A H 0.1512 0.8865 0.9446 0.079 Uiso 1 1 calc R U . . .
H12B H 0.0438 0.7891 0.8423 0.079 Uiso 1 1 calc R U . . .
C9 C 0.0668(3) 0.1530(2) 0.6611(2) 0.0349(5) Uani 1 1 d . . . . .
H9 H 0.0815 0.2234 0.7275 0.042 Uiso 1 1 calc R U . . .
O14 O 0.0376(4) 0.8853(3) 1.1008(3) 0.0863(10) Uani 1 1 d . . . . .
C11 C 0.3474(2) 0.5837(3) 0.4456(2) 0.0323(5) Uani 1 1 d . . . . .
H11 H 0.2811 0.6241 0.4280 0.039 Uiso 1 1 calc R U . . .
N10 N 0.2482(4) 0.1234(4) 0.2152(3) 0.0714(10) Uani 1 1 d . . . . .
H2A H 0.1887 0.0528 0.1962 0.086 Uiso 1 1 calc R U . . .
H2B H 0.3055 0.1306 0.1758 0.086 Uiso 1 1 calc R U . . .
C13 C -0.3073(3) 0.2616(3) 0.2766(3) 0.0513(8) Uani 1 1 d . . . . .
H13A H -0.3463 0.3300 0.2966 0.077 Uiso 1 1 calc R U . . .
H13B H -0.3558 0.1860 0.2898 0.077 Uiso 1 1 calc R U . . .
H13C H -0.3087 0.2460 0.1908 0.077 Uiso 1 1 calc R U . . .
N15 N 0.5191(4) 0.8971(4) 0.1164(4) 0.0715(9) Uani 1 1 d . . . . .
H9A H 0.5664 0.9311 0.0757 0.086 Uiso 1 1 calc R U . . .
H9B H 0.5482 0.8515 0.1632 0.086 Uiso 1 1 calc R U . . .
O16 O 0.3640(5) -0.1403(4) 0.3995(5) 0.1165(15) Uani 1 1 d . . . . .
C16 C 0.3029(9) -0.0779(8) 0.4362(9) 0.124(3) Uani 1 1 d . . . . .
H039 H 0.2158 -0.1148 0.3894 0.149 Uiso 1 1 calc R U . . .
C15 C 0.4081(5) 0.9140(5) 0.1073(5) 0.0766(12) Uani 1 1 d . . . . .
H044 H 0.3610 0.8752 0.1531 0.092 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 O5A 2.3552(18) . ?
Eu1 O12B 2.3723(17) 2_566 ?
Eu1 O10 2.4210(19) . ?
Eu1 O9 2.4502(19) . ?
Eu1 O1 2.4587(16) . ?
Eu1 O2 2.4590(18) . ?
Eu1 O11 2.5044(18) . ?
Eu1 O12A 2.5274(19) . ?
Eu1 O12B 2.5936(17) . ?
Eu1 C12 2.948(2) . ?
Eu1 Eu1 4.0585(3) 2_566 ?
F7 C7 1.348(3) . ?
C4 F4 1.342(3) . ?
C4 C2 1.377(4) . ?
C4 C3 1.382(3) 2_565 ?
O12B C12 1.276(3) . ?
O12B Eu1 2.3723(17) 2_566 ?
F8 C8 1.345(3) . ?
O9 C9 1.233(3) . ?
O1 C1 1.242(3) . ?
O11 C11 1.237(3) . ?
O5A C5 1.247(3) . ?
O12A C12 1.244(3) . ?
O10 C10 1.229(4) . ?
F3 C3 1.338(3) . ?
O2 C1 1.241(3) 2_566 ?
C1 O2 1.241(3) 2_566 ?
C1 C2 1.527(3) . ?
O5B C5 1.224(4) . ?
C14 O14 1.203(5) . ?
C14 N14 1.282(6) . ?
C14 H14 0.9300 . ?
C2 C3 1.373(3) . ?
O15 C15 1.240(5) . ?
C6 C7 1.374(3) . ?
C6 C8 1.377(4) . ?
C6 C5 1.525(3) . ?
C3 C4 1.382(3) 2_565 ?
N11 C11 1.309(3) . ?
N11 H3A 0.8600 . ?
N11 H3B 0.8600 . ?
C7 C8 1.375(4) 2_667 ?
C12 C13 1.494(4) . ?
N9 C9 1.299(3) . ?
N9 H1A 0.8600 . ?
N9 H1B 0.8600 . ?
N16 C16 1.153(9) . ?
N16 H40A 0.8600 . ?
N16 H40B 0.8600 . ?
C10 N10 1.295(4) . ?
C10 H10 0.9300 . ?
C8 C7 1.375(4) 2_667 ?
N14 H12A 0.8600 . ?
N14 H12B 0.8600 . ?
C9 H9 0.9300 . ?
C11 H11 0.9300 . ?
N10 H2A 0.8600 . ?
N10 H2B 0.8600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
N15 C15 1.249(6) . ?
N15 H9A 0.8600 . ?
N15 H9B 0.8600 . ?
O16 C16 1.146(7) . ?
C16 H039 0.9300 . ?
C15 H044 0.9300 . ?

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
O5A Eu1 O12B 90.73(7) . 2_566 ?
O5A Eu1 O10 94.03(8) . . ?
O12B Eu1 O10 142.76(6) 2_566 . ?
O5A Eu1 O9 76.18(7) . . ?
O12B Eu1 O9 144.72(6) 2_566 . ?
O10 Eu1 O9 71.75(7) . . ?
O5A Eu1 O1 137.97(7) . . ?
O12B Eu1 O1 76.54(6) 2_566 . ?
O10 Eu1 O1 75.36(6) . . ?
O9 Eu1 O1 133.94(6) . . ?
O5A Eu1 O2 74.11(8) . . ?
O12B Eu1 O2 72.81(6) 2_566 . ?
O10 Eu1 O2 143.70(7) . . ?
O9 Eu1 O2 72.12(7) . . ?
O1 Eu1 O2 135.52(6) . . ?
O5A Eu1 O11 67.80(7) . . ?
O12B Eu1 O11 75.49(6) 2_566 . ?
O10 Eu1 O11 72.33(7) . . ?
O9 Eu1 O11 126.13(7) . . ?
O1 Eu1 O11 70.24(6) . . ?
O2 Eu1 O11 129.31(7) . . ?
O5A Eu1 O12A 145.71(7) . . ?
O12B Eu1 O12A 118.75(6) 2_566 . ?
O10 Eu1 O12A 73.46(7) . . ?
O9 Eu1 O12A 69.60(7) . . ?
O1 Eu1 O12A 70.73(7) . . ?
O2 Eu1 O12A 96.98(7) . . ?
O11 Eu1 O12A 133.06(7) . . ?
O5A Eu1 O12B 142.72(7) . . ?
O12B Eu1 O12B 70.46(6) 2_566 . ?
O10 Eu1 O12B 120.63(6) . . ?
O9 Eu1 O12B 100.52(7) . . ?
O1 Eu1 O12B 70.08(6) . . ?
O2 Eu1 O12B 69.71(6) . . ?
O11 Eu1 O12B 132.30(6) . . ?
O12A Eu1 O12B 50.30(6) . . ?
O5A Eu1 C12 154.93(7) . . ?
O12B Eu1 C12 94.70(6) 2_566 . ?
O10 Eu1 C12 96.30(7) . . ?
O9 Eu1 C12 85.47(7) . . ?
O1 Eu1 C12 66.98(6) . . ?
O2 Eu1 C12 84.16(7) . . ?
O11 Eu1 C12 137.22(6) . . ?
O12A Eu1 C12 24.75(6) . . ?
O12B Eu1 C12 25.61(6) . . ?
O5A Eu1 Eu1 121.06(5) . 2_566 ?
O12B Eu1 Eu1 37.03(4) 2_566 2_566 ?
O10 Eu1 Eu1 142.27(5) . 2_566 ?
O9 Eu1 Eu1 126.43(5) . 2_566 ?
O1 Eu1 Eu1 69.28(4) . 2_566 ?
O2 Eu1 Eu1 66.77(4) . 2_566 ?
O11 Eu1 Eu1 106.47(4) . 2_566 ?
O12A Eu1 Eu1 82.70(4) . 2_566 ?
O12B Eu1 Eu1 33.43(4) . 2_566 ?
C12 Eu1 Eu1 58.10(5) . 2_566 ?
F4 C4 C2 119.8(2) . . ?
F4 C4 C3 118.6(2) . 2_565 ?
C2 C4 C3 121.5(2) . 2_565 ?
C12 O12B Eu1 150.40(16) . 2_566 ?
C12 O12B Eu1 92.92(14) . . ?
Eu1 O12B Eu1 109.54(6) 2_566 . ?
C9 O9 Eu1 129.56(17) . . ?
C1 O1 Eu1 134.80(15) . . ?
C11 O11 Eu1 127.44(17) . . ?
C5 O5A Eu1 147.03(19) . . ?
C12 O12A Eu1 96.92(14) . . ?
C10 O10 Eu1 137.2(2) . . ?
C1 O2 Eu1 138.31(16) 2_566 . ?
O2 C1 O1 128.5(2) 2_566 . ?
O2 C1 C2 116.2(2) 2_566 . ?
O1 C1 C2 115.2(2) . . ?
O14 C14 N14 125.4(4) . . ?
O14 C14 H14 117.3 . . ?
N14 C14 H14 117.3 . . ?
C3 C2 C4 117.0(2) . . ?
C3 C2 C1 122.3(2) . . ?
C4 C2 C1 120.6(2) . . ?
C7 C6 C8 116.6(2) . . ?
C7 C6 C5 121.5(2) . . ?
C8 C6 C5 121.8(2) . . ?
F3 C3 C2 120.0(2) . . ?
F3 C3 C4 118.5(2) . 2_565 ?
C2 C3 C4 121.4(2) . 2_565 ?
C11 N11 H3A 120.0 . . ?
C11 N11 H3B 120.0 . . ?
H3A N11 H3B 120.0 . . ?
F7 C7 C6 119.7(2) . . ?
F7 C7 C8 118.4(2) . 2_667 ?
C6 C7 C8 121.8(2) . 2_667 ?
O12A C12 O12B 119.6(2) . . ?
O12A C12 C13 121.1(2) . . ?
O12B C12 C13 119.3(2) . . ?
O12A C12 Eu1 58.32(13) . . ?
O12B C12 Eu1 61.47(12) . . ?
C13 C12 Eu1 174.9(2) . . ?
C9 N9 H1A 120.0 . . ?
C9 N9 H1B 120.0 . . ?
H1A N9 H1B 120.0 . . ?
C16 N16 H40A 120.0 . . ?
C16 N16 H40B 120.0 . . ?
H40A N16 H40B 120.0 . . ?
O10 C10 N10 125.1(4) . . ?
O10 C10 H10 117.5 . . ?
N10 C10 H10 117.5 . . ?
F8 C8 C7 118.4(2) . 2_667 ?
F8 C8 C6 120.0(2) . . ?
C7 C8 C6 121.6(2) 2_667 . ?
O5B C5 O5A 127.4(2) . . ?
O5B C5 C6 117.0(2) . . ?
O5A C5 C6 115.5(2) . . ?
C14 N14 H12A 120.0 . . ?
C14 N14 H12B 120.0 . . ?
H12A N14 H12B 120.0 . . ?
O9 C9 N9 124.7(3) . . ?
O9 C9 H9 117.6 . . ?
N9 C9 H9 117.6 . . ?
O11 C11 N11 124.0(3) . . ?
O11 C11 H11 118.0 . . ?
N11 C11 H11 118.0 . . ?
C10 N10 H2A 120.0 . . ?
C10 N10 H2B 120.0 . . ?
H2A N10 H2B 120.0 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C15 N15 H9A 120.0 . . ?
C15 N15 H9B 120.0 . . ?
H9A N15 H9B 120.0 . . ?
O16 C16 N16 144.3(11) . . ?
O16 C16 H039 107.9 . . ?
N16 C16 H039 107.9 . . ?
O15 C15 N15 126.8(5) . . ?
O15 C15 H044 116.6 . . ?
N15 C15 H044 116.6 . . ?

_refine_diff_density_max         0.737
_refine_diff_density_min         -0.859
_refine_diff_density_rms         0.095

_shelxl_version_number           2013-4


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: formamide'
_exptl_crystal_preparation       Luminescent
####################################################################### 
# 
# 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_shelxl
_database_code_depnum_ccdc_archive 'CCDC 1025458'
_audit_update_record             
;
2014-09-19 deposited with the CCDC.
2015-02-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H12 F4 Ho N O9 S2'
_chemical_formula_weight         619.28

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'
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'
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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

_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, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'

_cell_length_a                   15.4609(17)
_cell_length_b                   15.0599(15)
_cell_length_c                   16.7057(15)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3889.7(7)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    8551
_cell_measurement_theta_min      1.91
_cell_measurement_theta_max      54.78

_exptl_crystal_description       block
_exptl_crystal_colour            pink
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.115
_exptl_crystal_F_000             2384
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?

_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_absorpt_coefficient_mu    4.366
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.4735
_exptl_absorpt_correction_T_max  0.6005
_exptl_absorpt_process_details   'STOE XRed, XShape'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'STOE IPDS II'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            50858
_diffrn_reflns_av_unetI/netI     0.1037
_diffrn_reflns_av_R_equivalents  0.1880
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.247
_diffrn_reflns_theta_max         27.268
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.940
_diffrn_measured_fraction_theta_full 0.944
_diffrn_reflns_Laue_measured_fraction_max 0.940
_diffrn_reflns_Laue_measured_fraction_full 0.944
_diffrn_reflns_point_group_measured_fraction_max 0.940
_diffrn_reflns_point_group_measured_fraction_full 0.944
_reflns_number_total             4107
_reflns_number_gt                2159
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0219P)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         4107
_refine_ls_number_parameters     266
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1217
_refine_ls_R_factor_gt           0.0469
_refine_ls_wR_factor_ref         0.0749
_refine_ls_wR_factor_gt          0.0606
_refine_ls_goodness_of_fit_ref   0.903
_refine_ls_restrained_S_all      0.903
_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 0.47479(2) 0.50538(3) -0.36947(2) 0.02201(8) Uani 1 1 d . . . . .
S20 S 0.65766(15) 0.52239(14) -0.23923(16) 0.0377(6) Uani 1 1 d . . . . .
S30 S 0.45829(15) 0.70764(15) -0.27521(16) 0.0387(6) Uani 1 1 d . . . . .
F3 F 0.2362(4) 0.3838(4) -0.4724(5) 0.054(2) Uani 1 1 d . . . . .
F4 F 0.4404(4) 0.1748(4) -0.5642(5) 0.057(2) Uani 1 1 d . . . . .
F5 F 0.3141(4) 0.0533(4) -0.5788(5) 0.0584(19) Uani 1 1 d . . . . .
F8 F 0.1112(4) 0.2623(4) -0.4867(4) 0.0467(17) Uani 1 1 d . . . . .
O1 O 0.4350(5) 0.3754(4) -0.4398(4) 0.0346(16) Uani 1 1 d . . . . .
O2 O 0.5595(4) 0.6149(4) -0.4255(4) 0.0318(15) Uani 1 1 d . . . . .
O3 O 0.4515(5) 0.3854(5) -0.2742(5) 0.046(2) Uani 1 1 d . . . . .
O4 O 0.3384(5) 0.4535(5) -0.3126(5) 0.050(2) Uani 1 1 d . . . . .
O5 O 0.3257(6) 0.3300(6) -0.2451(7) 0.081(3) Uani 1 1 d . . . . .
O6 O 0.6044(4) 0.4286(4) -0.3943(4) 0.0320(15) Uani 1 1 d . . . . .
O7 O 0.3883(4) 0.5539(4) -0.4721(4) 0.0373(16) Uani 1 1 d . . . . .
O20 O 0.5633(4) 0.5403(4) -0.2616(4) 0.0362(15) Uani 1 1 d . . . . .
O30 O 0.4116(5) 0.6260(4) -0.3090(5) 0.0358(17) Uani 1 1 d . . . . .
N3 N 0.3702(6) 0.3870(6) -0.2770(6) 0.043(2) Uani 1 1 d . . . . .
C1 C 0.4131(6) 0.3540(5) -0.5105(6) 0.029(2) Uani 1 1 d . . . . .
C2 C 0.3425(7) 0.2824(6) -0.5173(6) 0.027(2) Uani 1 1 d . . . . .
C3 C 0.2596(7) 0.3023(5) -0.4981(7) 0.028(2) Uani 1 1 d . . . . .
C4 C 0.3590(6) 0.1978(6) -0.5460(6) 0.031(2) Uani 1 1 d . . . . .
C5 C 0.2927(6) 0.1361(6) -0.5533(6) 0.029(2) Uani 1 1 d . . . . .
C6 C 0.6370(5) 0.4126(6) -0.4619(6) 0.030(2) Uani 1 1 d . . . . .
C7 C 0.2095(6) 0.1543(5) -0.5329(5) 0.0235(18) Uani 1 1 d . . . . .
C8 C 0.1927(7) 0.2395(6) -0.5042(7) 0.028(2) Uani 1 1 d . . . . .
C20 C 0.6716(8) 0.5711(10) -0.1447(8) 0.074(4) Uani 1 1 d . . . . .
H1 H 0.6478 0.5328 -0.1044 0.111 Uiso 1 1 calc R U . . .
H2 H 0.6425 0.6274 -0.1433 0.111 Uiso 1 1 calc R U . . .
H3 H 0.7322 0.5797 -0.1347 0.111 Uiso 1 1 calc R U . . .
C21 C 0.7204(8) 0.5967(9) -0.2950(9) 0.067(4) Uani 1 1 d . . . . .
H10A H 0.6942 0.6545 -0.2935 0.101 Uiso 1 1 calc R U . . .
H10B H 0.7238 0.5765 -0.3494 0.101 Uiso 1 1 calc R U . . .
H10C H 0.7775 0.5998 -0.2726 0.101 Uiso 1 1 calc R U . . .
C30 C 0.3822(8) 0.7952(7) -0.2894(9) 0.065(4) Uani 1 1 d . . . . .
H7 H 0.3255 0.7748 -0.2749 0.097 Uiso 1 1 calc R U . . .
H8 H 0.3823 0.8130 -0.3446 0.097 Uiso 1 1 calc R U . . .
H9 H 0.3979 0.8448 -0.2564 0.097 Uiso 1 1 calc R U . . .
C31 C 0.4464(9) 0.6964(9) -0.1700(7) 0.063(4) Uani 1 1 d . . . . .
H4 H 0.4666 0.6389 -0.1537 0.094 Uiso 1 1 calc R U . . .
H5 H 0.3865 0.7027 -0.1559 0.094 Uiso 1 1 calc R U . . .
H6 H 0.4797 0.7415 -0.1435 0.094 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 O7 2.294(6) . ?
Ho1 O30 2.297(6) . ?
Ho1 O2 2.306(6) . ?
Ho1 O20 2.323(6) . ?
Ho1 O6 2.351(6) . ?
Ho1 O1 2.365(6) . ?
Ho1 O3 2.434(7) . ?
Ho1 O4 2.442(7) . ?
Ho1 N3 2.860(8) . ?
S20 O20 1.530(6) . ?
S20 C21 1.749(12) . ?
S20 C20 1.755(12) . ?
S30 O30 1.534(7) . ?
S30 C31 1.776(12) . ?
S30 C30 1.782(10) . ?
F3 C3 1.350(10) . ?
F4 C4 1.340(10) . ?
F5 C5 1.359(10) . ?
F8 C8 1.339(11) . ?
O1 C1 1.270(12) . ?
O2 C1 1.241(11) 5_664 ?
O3 N3 1.258(10) . ?
O4 N3 1.264(11) . ?
O5 N3 1.223(11) . ?
O6 C6 1.259(11) . ?
O7 C6 1.274(11) 5_664 ?
C1 O2 1.241(11) 5_664 ?
C1 C2 1.540(12) . ?
C2 C3 1.355(13) . ?
C2 C4 1.385(13) . ?
C3 C8 1.405(13) . ?
C4 C5 1.389(12) . ?
C5 C7 1.359(12) . ?
C6 O7 1.274(11) 5_664 ?
C6 C7 1.510(11) 3_554 ?
C7 C8 1.394(12) . ?
C7 C6 1.510(11) 3_454 ?
C20 H1 0.9600 . ?
C20 H2 0.9600 . ?
C20 H3 0.9600 . ?
C21 H10A 0.9600 . ?
C21 H10B 0.9600 . ?
C21 H10C 0.9600 . ?
C30 H7 0.9600 . ?
C30 H8 0.9600 . ?
C30 H9 0.9600 . ?
C31 H4 0.9600 . ?
C31 H5 0.9600 . ?
C31 H6 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
O7 Ho1 O30 80.2(3) . . ?
O7 Ho1 O2 78.4(2) . . ?
O30 Ho1 O2 81.7(2) . . ?
O7 Ho1 O20 148.3(2) . . ?
O30 Ho1 O20 74.3(2) . . ?
O2 Ho1 O20 79.5(2) . . ?
O7 Ho1 O6 121.4(2) . . ?
O30 Ho1 O6 146.1(2) . . ?
O2 Ho1 O6 78.2(2) . . ?
O20 Ho1 O6 75.3(2) . . ?
O7 Ho1 O1 75.0(2) . . ?
O30 Ho1 O1 139.7(2) . . ?
O2 Ho1 O1 122.6(2) . . ?
O20 Ho1 O1 136.6(2) . . ?
O6 Ho1 O1 74.1(2) . . ?
O7 Ho1 O3 129.7(2) . . ?
O30 Ho1 O3 103.6(3) . . ?
O2 Ho1 O3 151.7(2) . . ?
O20 Ho1 O3 75.4(2) . . ?
O6 Ho1 O3 82.9(2) . . ?
O1 Ho1 O3 70.8(3) . . ?
O7 Ho1 O4 83.6(3) . . ?
O30 Ho1 O4 73.4(2) . . ?
O2 Ho1 O4 151.4(2) . . ?
O20 Ho1 O4 106.2(3) . . ?
O6 Ho1 O4 130.4(2) . . ?
O1 Ho1 O4 72.8(2) . . ?
O3 Ho1 O4 51.7(2) . . ?
O7 Ho1 N3 105.8(3) . . ?
O30 Ho1 N3 90.8(3) . . ?
O2 Ho1 N3 170.7(2) . . ?
O20 Ho1 N3 93.2(3) . . ?
O6 Ho1 N3 105.7(2) . . ?
O1 Ho1 N3 66.8(3) . . ?
O3 Ho1 N3 25.9(2) . . ?
O4 Ho1 N3 26.1(2) . . ?
O20 S20 C21 106.6(5) . . ?
O20 S20 C20 105.3(5) . . ?
C21 S20 C20 98.3(8) . . ?
O30 S30 C31 103.8(5) . . ?
O30 S30 C30 103.5(5) . . ?
C31 S30 C30 97.7(7) . . ?
C1 O1 Ho1 137.9(6) . . ?
C1 O2 Ho1 144.4(6) 5_664 . ?
N3 O3 Ho1 96.3(5) . . ?
N3 O4 Ho1 95.8(6) . . ?
C6 O6 Ho1 126.4(6) . . ?
C6 O7 Ho1 162.1(6) 5_664 . ?
S20 O20 Ho1 135.3(4) . . ?
S30 O30 Ho1 126.5(4) . . ?
O5 N3 O3 122.2(9) . . ?
O5 N3 O4 122.9(10) . . ?
O3 N3 O4 114.9(8) . . ?
O5 N3 Ho1 172.5(9) . . ?
O3 N3 Ho1 57.8(5) . . ?
O4 N3 Ho1 58.1(5) . . ?
O2 C1 O1 127.9(8) 5_664 . ?
O2 C1 C2 116.3(9) 5_664 . ?
O1 C1 C2 115.8(9) . . ?
C3 C2 C4 117.4(9) . . ?
C3 C2 C1 119.9(9) . . ?
C4 C2 C1 122.6(9) . . ?
F3 C3 C2 122.0(8) . . ?
F3 C3 C8 116.0(9) . . ?
C2 C3 C8 122.0(9) . . ?
F4 C4 C2 119.3(8) . . ?
F4 C4 C5 120.0(8) . . ?
C2 C4 C5 120.6(8) . . ?
C7 C5 F5 119.6(8) . . ?
C7 C5 C4 122.8(8) . . ?
F5 C5 C4 117.5(8) . . ?
O6 C6 O7 125.3(8) . 5_664 ?
O6 C6 C7 118.4(9) . 3_554 ?
O7 C6 C7 116.2(9) 5_664 3_554 ?
C5 C7 C8 116.6(8) . . ?
C5 C7 C6 123.6(8) . 3_454 ?
C8 C7 C6 119.7(8) . 3_454 ?
F8 C8 C7 119.1(8) . . ?
F8 C8 C3 120.3(9) . . ?
C7 C8 C3 120.5(10) . . ?
S20 C20 H1 109.5 . . ?
S20 C20 H2 109.5 . . ?
H1 C20 H2 109.5 . . ?
S20 C20 H3 109.5 . . ?
H1 C20 H3 109.5 . . ?
H2 C20 H3 109.5 . . ?
S20 C21 H10A 109.5 . . ?
S20 C21 H10B 109.5 . . ?
H10A C21 H10B 109.5 . . ?
S20 C21 H10C 109.5 . . ?
H10A C21 H10C 109.5 . . ?
H10B C21 H10C 109.5 . . ?
S30 C30 H7 109.5 . . ?
S30 C30 H8 109.5 . . ?
H7 C30 H8 109.5 . . ?
S30 C30 H9 109.5 . . ?
H7 C30 H9 109.5 . . ?
H8 C30 H9 109.5 . . ?
S30 C31 H4 109.5 . . ?
S30 C31 H5 109.5 . . ?
H4 C31 H5 109.5 . . ?
S30 C31 H6 109.5 . . ?
H4 C31 H6 109.5 . . ?
H5 C31 H6 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
C21 S20 O20 Ho1 77.6(8) . . . . ?
C20 S20 O20 Ho1 -178.7(7) . . . . ?
C31 S30 O30 Ho1 -109.7(7) . . . . ?
C30 S30 O30 Ho1 148.8(7) . . . . ?
Ho1 O3 N3 O5 171.2(10) . . . . ?
Ho1 O3 N3 O4 -11.4(9) . . . . ?
Ho1 O4 N3 O5 -171.2(10) . . . . ?
Ho1 O4 N3 O3 11.3(9) . . . . ?
Ho1 O1 C1 O2 36.0(15) . . . 5_664 ?
Ho1 O1 C1 C2 -142.3(7) . . . . ?
O2 C1 C2 C3 -106.5(11) 5_664 . . . ?
O1 C1 C2 C3 72.0(12) . . . . ?
O2 C1 C2 C4 70.4(12) 5_664 . . . ?
O1 C1 C2 C4 -111.0(11) . . . . ?
C4 C2 C3 F3 -177.5(10) . . . . ?
C1 C2 C3 F3 -0.4(16) . . . . ?
C4 C2 C3 C8 2.2(16) . . . . ?
C1 C2 C3 C8 179.3(11) . . . . ?
C3 C2 C4 F4 -178.7(9) . . . . ?
C1 C2 C4 F4 4.3(15) . . . . ?
C3 C2 C4 C5 -1.1(15) . . . . ?
C1 C2 C4 C5 -178.1(9) . . . . ?
F4 C4 C5 C7 177.4(9) . . . . ?
C2 C4 C5 C7 -0.2(15) . . . . ?
F4 C4 C5 F5 0.2(14) . . . . ?
C2 C4 C5 F5 -177.4(9) . . . . ?
Ho1 O6 C6 O7 10.6(12) . . . 5_664 ?
Ho1 O6 C6 C7 -166.7(5) . . . 3_554 ?
F5 C5 C7 C8 177.5(9) . . . . ?
C4 C5 C7 C8 0.3(14) . . . . ?
F5 C5 C7 C6 -1.0(14) . . . 3_454 ?
C4 C5 C7 C6 -178.2(10) . . . 3_454 ?
C5 C7 C8 F8 177.0(9) . . . . ?
C6 C7 C8 F8 -4.4(15) 3_454 . . . ?
C5 C7 C8 C3 0.7(15) . . . . ?
C6 C7 C8 C3 179.3(10) 3_454 . . . ?
F3 C3 C8 F8 1.4(16) . . . . ?
C2 C3 C8 F8 -178.3(10) . . . . ?
F3 C3 C8 C7 177.7(9) . . . . ?
C2 C3 C8 C7 -2.0(18) . . . . ?

_refine_diff_density_max         1.033
_refine_diff_density_min         -1.248
_refine_diff_density_rms         0.184

_shelxl_version_number           2013-4


_exptl_crystal_recrystallization_method 'diffusion controlled crystallization'
####################################################################### 
# 
# 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_shelxl
_database_code_depnum_ccdc_archive 'CCDC 1025459'
_audit_update_record             
;
2014-09-19 deposited with the CCDC.
2015-02-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H12 Er F4 N O9 S2'
_chemical_formula_weight         621.61

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'
Er Er -0.2586 4.9576 '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'
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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

_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, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'

_cell_length_a                   15.4177(13)
_cell_length_b                   15.0482(9)
_cell_length_c                   16.6749(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3868.7(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    25119
_cell_measurement_theta_min      1.91
_cell_measurement_theta_max      54.78

_exptl_crystal_description       block
_exptl_crystal_colour            pink
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.134
_exptl_crystal_F_000             2392
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.25
_exptl_absorpt_coefficient_mu    4.638
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.4140
_exptl_absorpt_correction_T_max  0.5704
_exptl_absorpt_process_details   'STOE XRed, XShape'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'STOE IPDS II'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            40534
_diffrn_reflns_av_unetI/netI     0.0179
_diffrn_reflns_av_R_equivalents  0.0453
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.251
_diffrn_reflns_theta_max         27.323
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4305
_reflns_number_gt                3635
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0451P)²+18.7498P] 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     SHELXL
_refine_ls_extinction_coef       0.00056(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4305
_refine_ls_number_parameters     267
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0440
_refine_ls_R_factor_gt           0.0351
_refine_ls_wR_factor_ref         0.1013
_refine_ls_wR_factor_gt          0.0889
_refine_ls_goodness_of_fit_ref   1.105
_refine_ls_restrained_S_all      1.105
_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
Er1 Er 0.47503(2) 0.50503(2) -0.36985(2) 0.02379(11) Uani 1 1 d . . . . .
S20 S 0.65745(10) 0.52093(11) -0.23979(10) 0.0423(3) Uani 1 1 d . . . . .
S30 S 0.45862(10) 0.70633(11) -0.27444(10) 0.0434(4) Uani 1 1 d . . . . .
F3 F 0.2368(2) 0.3847(2) -0.4729(3) 0.0611(11) Uani 1 1 d . . . . .
F4 F 0.4400(2) 0.1758(3) -0.5658(3) 0.0638(12) Uani 1 1 d . . . . .
F5 F 0.3143(2) 0.0536(3) -0.5787(3) 0.0634(12) Uani 1 1 d . . . . .
F8 F 0.1111(2) 0.2631(3) -0.4862(3) 0.0551(10) Uani 1 1 d . . . . .
O1 O 0.4340(3) 0.3767(3) -0.4417(2) 0.0372(9) Uani 1 1 d . . . . .
O2 O 0.5603(3) 0.6149(3) -0.4253(2) 0.0383(9) Uani 1 1 d . . . . .
O3 O 0.4528(3) 0.3845(3) -0.2754(3) 0.0524(12) Uani 1 1 d . . . . .
O4 O 0.3384(3) 0.4529(3) -0.3135(3) 0.0537(12) Uani 1 1 d . . . . .
O5 O 0.3262(4) 0.3307(4) -0.2449(4) 0.087(2) Uani 1 1 d . . . . .
O6 O 0.6038(2) 0.4278(3) -0.3961(2) 0.0373(9) Uani 1 1 d . . . . .
O7 O 0.3877(3) 0.5544(3) -0.4717(2) 0.0405(9) Uani 1 1 d . . . . .
O20 O 0.5634(3) 0.5397(3) -0.2624(2) 0.0397(9) Uani 1 1 d . . . . .
O30 O 0.4121(3) 0.6254(3) -0.3092(3) 0.0414(10) Uani 1 1 d . . . . .
N3 N 0.3712(4) 0.3868(4) -0.2767(3) 0.0493(13) Uani 1 1 d . . . . .
C1 C 0.4118(3) 0.3546(3) -0.5102(3) 0.0288(10) Uani 1 1 d . . . . .
C2 C 0.3424(3) 0.2832(4) -0.5175(3) 0.0309(11) Uani 1 1 d . . . . .
C3 C 0.2571(4) 0.3023(4) -0.4979(3) 0.0361(12) Uani 1 1 d . . . . .
C4 C 0.3587(3) 0.1989(4) -0.5456(4) 0.0377(12) Uani 1 1 d . . . . .
C5 C 0.2935(3) 0.1356(4) -0.5527(4) 0.0361(12) Uani 1 1 d . . . . .
C6 C 0.6355(3) 0.4122(3) -0.4637(3) 0.0306(11) Uani 1 1 d . . . . .
C7 C 0.2085(3) 0.1548(3) -0.5321(3) 0.0283(10) Uani 1 1 d . . . . .
C8 C 0.1929(3) 0.2407(4) -0.5046(3) 0.0349(12) Uani 1 1 d . . . . .
C20 C 0.6686(7) 0.5698(8) -0.1435(5) 0.096(4) Uani 1 1 d . . . . .
H1 H 0.6332 0.5381 -0.1057 0.144 Uiso 1 1 calc R U . . .
H2 H 0.6505 0.6307 -0.1457 0.144 Uiso 1 1 calc R U . . .
H3 H 0.7282 0.5668 -0.1270 0.144 Uiso 1 1 calc R U . . .
C21 C 0.7208(5) 0.5969(6) -0.2953(5) 0.068(2) Uani 1 1 d . . . . .
H10A H 0.7000 0.6562 -0.2862 0.102 Uiso 1 1 calc R U . . .
H10B H 0.7167 0.5831 -0.3514 0.102 Uiso 1 1 calc R U . . .
H10C H 0.7803 0.5927 -0.2785 0.102 Uiso 1 1 calc R U . . .
C30 C 0.3839(5) 0.7937(5) -0.2904(6) 0.073(3) Uani 1 1 d . . . . .
H7 H 0.3261 0.7727 -0.2806 0.110 Uiso 1 1 calc R U . . .
H8 H 0.3883 0.8141 -0.3448 0.110 Uiso 1 1 calc R U . . .
H9 H 0.3967 0.8419 -0.2546 0.110 Uiso 1 1 calc R U . . .
C31 C 0.4459(6) 0.6957(6) -0.1687(5) 0.068(2) Uani 1 1 d . . . . .
H4 H 0.4720 0.6412 -0.1511 0.102 Uiso 1 1 calc R U . . .
H5 H 0.3853 0.6953 -0.1556 0.102 Uiso 1 1 calc R U . . .
H6 H 0.4736 0.7449 -0.1425 0.102 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
Er1 O30 2.290(4) . ?
Er1 O7 2.291(4) . ?
Er1 O2 2.306(4) . ?
Er1 O20 2.311(4) . ?
Er1 O6 2.342(4) . ?
Er1 O1 2.359(4) . ?
Er1 O3 2.427(5) . ?
Er1 O4 2.436(4) . ?
Er1 N3 2.853(5) . ?
S20 O20 1.524(4) . ?
S20 C21 1.766(8) . ?
S20 C20 1.774(8) . ?
S30 O30 1.528(4) . ?
S30 C30 1.769(8) . ?
S30 C31 1.781(8) . ?
F3 C3 1.345(6) . ?
F4 C4 1.343(6) . ?
F5 C5 1.347(6) . ?
F8 C8 1.342(6) . ?
O1 C1 1.238(6) . ?
O2 C1 1.246(6) 5_664 ?
O3 N3 1.260(7) . ?
O4 N3 1.273(7) . ?
O5 N3 1.214(7) . ?
O6 C6 1.251(7) . ?
O7 C6 1.241(6) 5_664 ?
C1 O2 1.246(6) 5_664 ?
C1 C2 1.520(7) . ?
C2 C4 1.376(8) . ?
C2 C3 1.386(8) . ?
C3 C8 1.360(8) . ?
C4 C5 1.390(7) . ?
C5 C7 1.385(7) . ?
C6 O7 1.241(6) 5_664 ?
C6 C7 1.513(7) 3_554 ?
C7 C8 1.393(8) . ?
C7 C6 1.513(7) 3_454 ?
C20 H1 0.9600 . ?
C20 H2 0.9600 . ?
C20 H3 0.9600 . ?
C21 H10A 0.9600 . ?
C21 H10B 0.9600 . ?
C21 H10C 0.9600 . ?
C30 H7 0.9600 . ?
C30 H8 0.9600 . ?
C30 H9 0.9600 . ?
C31 H4 0.9600 . ?
C31 H5 0.9600 . ?
C31 H6 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
O30 Er1 O7 79.72(15) . . ?
O30 Er1 O2 81.47(15) . . ?
O7 Er1 O2 78.74(15) . . ?
O30 Er1 O20 74.27(15) . . ?
O7 Er1 O20 148.00(16) . . ?
O2 Er1 O20 79.25(14) . . ?
O30 Er1 O6 146.53(14) . . ?
O7 Er1 O6 121.38(14) . . ?
O2 Er1 O6 78.32(15) . . ?
O20 Er1 O6 75.94(14) . . ?
O30 Er1 O1 139.29(14) . . ?
O7 Er1 O1 74.42(15) . . ?
O2 Er1 O1 122.40(14) . . ?
O20 Er1 O1 137.47(15) . . ?
O6 Er1 O1 74.12(14) . . ?
O30 Er1 O3 104.18(18) . . ?
O7 Er1 O3 129.84(15) . . ?
O2 Er1 O3 151.28(15) . . ?
O20 Er1 O3 75.44(16) . . ?
O6 Er1 O3 82.53(15) . . ?
O1 Er1 O3 71.33(16) . . ?
O30 Er1 O4 73.61(15) . . ?
O7 Er1 O4 83.22(16) . . ?
O2 Er1 O4 151.44(15) . . ?
O20 Er1 O4 106.48(16) . . ?
O6 Er1 O4 130.21(15) . . ?
O1 Er1 O4 72.57(16) . . ?
O3 Er1 O4 52.21(15) . . ?
O30 Er1 N3 90.86(16) . . ?
O7 Er1 N3 106.01(17) . . ?
O2 Er1 N3 170.20(16) . . ?
O20 Er1 N3 92.85(16) . . ?
O6 Er1 N3 105.57(16) . . ?
O1 Er1 N3 67.39(16) . . ?
O3 Er1 N3 26.04(16) . . ?
O4 Er1 N3 26.38(16) . . ?
O20 S20 C21 106.1(3) . . ?
O20 S20 C20 103.8(4) . . ?
C21 S20 C20 98.8(5) . . ?
O30 S30 C30 103.3(3) . . ?
O30 S30 C31 104.6(3) . . ?
C30 S30 C31 98.3(4) . . ?
C1 O1 Er1 139.8(4) . . ?
C1 O2 Er1 143.9(4) 5_664 . ?
N3 O3 Er1 96.2(4) . . ?
N3 O4 Er1 95.4(3) . . ?
C6 O6 Er1 126.3(3) . . ?
C6 O7 Er1 160.7(4) 5_664 . ?
S20 O20 Er1 135.3(2) . . ?
S30 O30 Er1 126.8(2) . . ?
O5 N3 O3 122.9(6) . . ?
O5 N3 O4 121.8(6) . . ?
O3 N3 O4 115.3(5) . . ?
O5 N3 Er1 172.6(6) . . ?
O3 N3 Er1 57.7(3) . . ?
O4 N3 Er1 58.2(3) . . ?
O1 C1 O2 126.9(5) . 5_664 ?
O1 C1 C2 117.3(5) . . ?
O2 C1 C2 115.8(4) 5_664 . ?
C4 C2 C3 116.3(5) . . ?
C4 C2 C1 123.4(5) . . ?
C3 C2 C1 120.2(5) . . ?
F3 C3 C8 119.0(5) . . ?
F3 C3 C2 119.0(5) . . ?
C8 C3 C2 122.0(5) . . ?
F4 C4 C2 119.6(5) . . ?
F4 C4 C5 118.4(5) . . ?
C2 C4 C5 122.0(5) . . ?
F5 C5 C7 119.8(5) . . ?
F5 C5 C4 118.9(5) . . ?
C7 C5 C4 121.4(5) . . ?
O7 C6 O6 126.5(5) 5_664 . ?
O7 C6 C7 116.3(5) 5_664 3_554 ?
O6 C6 C7 117.2(5) . 3_554 ?
C5 C7 C8 116.0(5) . . ?
C5 C7 C6 123.6(5) . 3_454 ?
C8 C7 C6 120.4(5) . 3_454 ?
F8 C8 C3 119.7(5) . . ?
F8 C8 C7 118.0(5) . . ?
C3 C8 C7 122.3(5) . . ?
S20 C20 H1 109.5 . . ?
S20 C20 H2 109.5 . . ?
H1 C20 H2 109.5 . . ?
S20 C20 H3 109.5 . . ?
H1 C20 H3 109.5 . . ?
H2 C20 H3 109.5 . . ?
S20 C21 H10A 109.5 . . ?
S20 C21 H10B 109.5 . . ?
H10A C21 H10B 109.5 . . ?
S20 C21 H10C 109.5 . . ?
H10A C21 H10C 109.5 . . ?
H10B C21 H10C 109.5 . . ?
S30 C30 H7 109.5 . . ?
S30 C30 H8 109.5 . . ?
H7 C30 H8 109.5 . . ?
S30 C30 H9 109.5 . . ?
H7 C30 H9 109.5 . . ?
H8 C30 H9 109.5 . . ?
S30 C31 H4 109.5 . . ?
S30 C31 H5 109.5 . . ?
H4 C31 H5 109.5 . . ?
S30 C31 H6 109.5 . . ?
H4 C31 H6 109.5 . . ?
H5 C31 H6 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
C21 S20 O20 Er1 78.8(5) . . . . ?
C20 S20 O20 Er1 -177.6(5) . . . . ?
C30 S30 O30 Er1 147.9(4) . . . . ?
C31 S30 O30 Er1 -109.7(4) . . . . ?
Er1 O3 N3 O5 171.3(7) . . . . ?
Er1 O3 N3 O4 -9.3(6) . . . . ?
Er1 O4 N3 O5 -171.3(7) . . . . ?
Er1 O4 N3 O3 9.2(6) . . . . ?
Er1 O1 C1 O2 36.6(9) . . . 5_664 ?
Er1 O1 C1 C2 -142.8(4) . . . . ?
O1 C1 C2 C4 -110.5(6) . . . . ?
O2 C1 C2 C4 70.0(7) 5_664 . . . ?
O1 C1 C2 C3 71.7(7) . . . . ?
O2 C1 C2 C3 -107.8(6) 5_664 . . . ?
C4 C2 C3 F3 -177.6(5) . . . . ?
C1 C2 C3 F3 0.4(8) . . . . ?
C4 C2 C3 C8 1.1(9) . . . . ?
C1 C2 C3 C8 179.0(5) . . . . ?
C3 C2 C4 F4 -179.9(6) . . . . ?
C1 C2 C4 F4 2.2(9) . . . . ?
C3 C2 C4 C5 -1.2(9) . . . . ?
C1 C2 C4 C5 -179.1(6) . . . . ?
F4 C4 C5 F5 0.5(9) . . . . ?
C2 C4 C5 F5 -178.3(6) . . . . ?
F4 C4 C5 C7 179.3(6) . . . . ?
C2 C4 C5 C7 0.5(10) . . . . ?
Er1 O6 C6 O7 11.7(8) . . . 5_664 ?
Er1 O6 C6 C7 -167.4(3) . . . 3_554 ?
F5 C5 C7 C8 179.1(5) . . . . ?
C4 C5 C7 C8 0.3(9) . . . . ?
F5 C5 C7 C6 0.6(9) . . . 3_454 ?
C4 C5 C7 C6 -178.2(5) . . . 3_454 ?
F3 C3 C8 F8 -0.1(9) . . . . ?
C2 C3 C8 F8 -178.8(5) . . . . ?
F3 C3 C8 C7 178.3(5) . . . . ?
C2 C3 C8 C7 -0.4(9) . . . . ?
C5 C7 C8 F8 178.1(5) . . . . ?
C6 C7 C8 F8 -3.4(8) 3_454 . . . ?
C5 C7 C8 C3 -0.3(9) . . . . ?
C6 C7 C8 C3 178.2(5) 3_454 . . . ?

_refine_diff_density_max         1.168
_refine_diff_density_min         -1.673
_refine_diff_density_rms         0.166

_shelxl_version_number           2013-4


_exptl_crystal_recrystallization_method 'diffusion controlled crystallization'
####################################################################### 
# 
# 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_shelxl
_database_code_depnum_ccdc_archive 'CCDC 1025460'
_audit_update_record             
;
2014-09-19 deposited with the CCDC.
2015-02-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H12 F4 N O9 S2 Tm'
_chemical_formula_weight         623.28

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'
F F 0.0171 0.0103 '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'
Tm Tm -0.3139 5.2483 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

_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, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'

_cell_length_a                   15.3508(4)
_cell_length_b                   14.9676(4)
_cell_length_c                   16.5758(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3808.5(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    22049
_cell_measurement_theta_min      1.91
_cell_measurement_theta_max      54.78

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.174
_exptl_crystal_F_000             2400
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_absorpt_coefficient_mu    4.963
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.2272
_exptl_absorpt_correction_T_max  0.6268
_exptl_absorpt_process_details   'STOE XRed, XShape'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'STOE IPDS II'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            43741
_diffrn_reflns_av_unetI/netI     0.0335
_diffrn_reflns_av_R_equivalents  0.0967
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.263
_diffrn_reflns_theta_max         26.786
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.941
_diffrn_measured_fraction_theta_full 0.944
_diffrn_reflns_Laue_measured_fraction_max 0.941
_diffrn_reflns_Laue_measured_fraction_full 0.944
_diffrn_reflns_point_group_measured_fraction_max 0.941
_diffrn_reflns_point_group_measured_fraction_full 0.944
_reflns_number_total             3828
_reflns_number_gt                2952
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0361P)²+1.1746P] 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         3828
_refine_ls_number_parameters     266
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0409
_refine_ls_R_factor_gt           0.0280
_refine_ls_wR_factor_ref         0.0686
_refine_ls_wR_factor_gt          0.0640
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.026
_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
Tm1 Tm 0.47501(2) 0.50510(2) -0.36955(2) 0.01912(7) Uani 1 1 d . . . . .
S20 S 0.65745(8) 0.52099(8) -0.23980(8) 0.0345(3) Uani 1 1 d . . . . .
S30 S 0.45864(8) 0.70656(8) -0.27488(8) 0.0356(3) Uani 1 1 d . . . . .
F3 F 0.23691(19) 0.38479(17) -0.4720(2) 0.0514(9) Uani 1 1 d . . . . .
F4 F 0.44090(18) 0.17491(19) -0.5654(2) 0.0512(9) Uani 1 1 d . . . . .
F5 F 0.31487(19) 0.05311(18) -0.5789(2) 0.0511(9) Uani 1 1 d . . . . .
F8 F 0.11069(17) 0.26270(18) -0.4859(2) 0.0443(7) Uani 1 1 d . . . . .
O1 O 0.4343(2) 0.37604(19) -0.44080(19) 0.0309(7) Uani 1 1 d . . . . .
O2 O 0.5597(2) 0.61477(19) -0.4250(2) 0.0302(7) Uani 1 1 d . . . . .
O3 O 0.4532(2) 0.3848(2) -0.2747(2) 0.0419(8) Uani 1 1 d . . . . .
O4 O 0.3385(2) 0.4526(2) -0.3136(2) 0.0449(9) Uani 1 1 d . . . . .
O5 O 0.3267(3) 0.3309(3) -0.2446(3) 0.0746(15) Uani 1 1 d . . . . .
O6 O 0.60394(19) 0.4283(2) -0.3956(2) 0.0299(7) Uani 1 1 d . . . . .
O7 O 0.3876(2) 0.5540(2) -0.4716(2) 0.0338(7) Uani 1 1 d . . . . .
O20 O 0.5633(2) 0.5404(2) -0.2620(2) 0.0332(7) Uani 1 1 d . . . . .
O30 O 0.4117(2) 0.6254(2) -0.3093(2) 0.0342(8) Uani 1 1 d . . . . .
N3 N 0.3713(3) 0.3872(3) -0.2761(3) 0.0379(10) Uani 1 1 d . . . . .
C1 C 0.4132(2) 0.3544(2) -0.5109(3) 0.0238(9) Uani 1 1 d . . . . .
C2 C 0.3432(3) 0.2830(3) -0.5173(3) 0.0251(9) Uani 1 1 d . . . . .
C3 C 0.2579(3) 0.3025(3) -0.4979(3) 0.0295(9) Uani 1 1 d . . . . .
C4 C 0.3592(3) 0.1979(3) -0.5457(3) 0.0281(9) Uani 1 1 d . . . . .
C5 C 0.2937(3) 0.1355(3) -0.5530(3) 0.0276(9) Uani 1 1 d . . . . .
C6 C 0.6357(3) 0.4132(3) -0.4632(3) 0.0250(9) Uani 1 1 d . . . . .
C7 C 0.2093(3) 0.1544(3) -0.5323(3) 0.0232(8) Uani 1 1 d . . . . .
C8 C 0.1930(3) 0.2403(3) -0.5043(3) 0.0278(9) Uani 1 1 d . . . . .
C20 C 0.6689(5) 0.5690(6) -0.1428(4) 0.078(2) Uani 1 1 d . . . . .
H1 H 0.6337 0.5366 -0.1049 0.118 Uiso 1 1 calc R U . . .
H2 H 0.6504 0.6302 -0.1444 0.118 Uiso 1 1 calc R U . . .
H3 H 0.7288 0.5662 -0.1265 0.118 Uiso 1 1 calc R U . . .
C21 C 0.7210(4) 0.5976(4) -0.2957(4) 0.0555(16) Uani 1 1 d . . . . .
H10A H 0.6984 0.6568 -0.2883 0.083 Uiso 1 1 calc R U . . .
H10B H 0.7189 0.5821 -0.3518 0.083 Uiso 1 1 calc R U . . .
H10C H 0.7802 0.5954 -0.2772 0.083 Uiso 1 1 calc R U . . .
C30 C 0.3827(4) 0.7944(4) -0.2896(5) 0.0597(18) Uani 1 1 d . . . . .
H7 H 0.3249 0.7728 -0.2794 0.090 Uiso 1 1 calc R U . . .
H8 H 0.3866 0.8155 -0.3442 0.090 Uiso 1 1 calc R U . . .
H9 H 0.3957 0.8425 -0.2532 0.090 Uiso 1 1 calc R U . . .
C31 C 0.4469(5) 0.6961(4) -0.1691(4) 0.0578(16) Uani 1 1 d . . . . .
H4 H 0.4733 0.6413 -0.1515 0.087 Uiso 1 1 calc R U . . .
H5 H 0.3861 0.6956 -0.1555 0.087 Uiso 1 1 calc R U . . .
H6 H 0.4748 0.7456 -0.1430 0.087 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
Tm1 O30 2.277(3) . ?
Tm1 O7 2.281(3) . ?
Tm1 O2 2.287(3) . ?
Tm1 O20 2.300(3) . ?
Tm1 O6 2.329(3) . ?
Tm1 O1 2.349(3) . ?
Tm1 O3 2.414(3) . ?
Tm1 O4 2.422(4) . ?
Tm1 N3 2.836(4) . ?
S20 O20 1.520(3) . ?
S20 C21 1.767(6) . ?
S20 C20 1.770(6) . ?
S30 O30 1.524(3) . ?
S30 C31 1.769(7) . ?
S30 C30 1.774(6) . ?
F3 C3 1.343(5) . ?
F4 C4 1.341(5) . ?
F5 C5 1.345(5) . ?
F8 C8 1.342(5) . ?
O1 C1 1.249(5) . ?
O2 C1 1.232(5) 5_664 ?
O3 N3 1.258(6) . ?
O4 N3 1.264(5) . ?
O5 N3 1.205(5) . ?
O6 C6 1.243(5) . ?
O7 C6 1.239(5) 5_664 ?
C1 O2 1.232(5) 5_664 ?
C1 C2 1.520(5) . ?
C2 C3 1.379(6) . ?
C2 C4 1.380(6) . ?
C3 C8 1.368(6) . ?
C4 C5 1.378(6) . ?
C5 C7 1.371(6) . ?
C6 O7 1.239(5) 5_664 ?
C6 C7 1.518(5) 3_554 ?
C7 C8 1.390(6) . ?
C7 C6 1.518(5) 3_454 ?
C20 H1 0.9600 . ?
C20 H2 0.9600 . ?
C20 H3 0.9600 . ?
C21 H10A 0.9600 . ?
C21 H10B 0.9600 . ?
C21 H10C 0.9600 . ?
C30 H7 0.9600 . ?
C30 H8 0.9600 . ?
C30 H9 0.9600 . ?
C31 H4 0.9600 . ?
C31 H5 0.9600 . ?
C31 H6 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
O30 Tm1 O7 79.65(12) . . ?
O30 Tm1 O2 81.46(12) . . ?
O7 Tm1 O2 78.83(12) . . ?
O30 Tm1 O20 74.35(12) . . ?
O7 Tm1 O20 147.99(11) . . ?
O2 Tm1 O20 79.12(12) . . ?
O30 Tm1 O6 146.57(11) . . ?
O7 Tm1 O6 121.38(12) . . ?
O2 Tm1 O6 78.26(11) . . ?
O20 Tm1 O6 75.91(11) . . ?
O30 Tm1 O1 139.23(11) . . ?
O7 Tm1 O1 74.59(11) . . ?
O2 Tm1 O1 122.65(11) . . ?
O20 Tm1 O1 137.32(11) . . ?
O6 Tm1 O1 74.13(11) . . ?
O30 Tm1 O3 104.18(14) . . ?
O7 Tm1 O3 129.88(12) . . ?
O2 Tm1 O3 151.15(12) . . ?
O20 Tm1 O3 75.42(12) . . ?
O6 Tm1 O3 82.55(12) . . ?
O1 Tm1 O3 71.17(12) . . ?
O30 Tm1 O4 73.69(12) . . ?
O7 Tm1 O4 83.05(13) . . ?
O2 Tm1 O4 151.46(11) . . ?
O20 Tm1 O4 106.71(13) . . ?
O6 Tm1 O4 130.24(11) . . ?
O1 Tm1 O4 72.29(12) . . ?
O3 Tm1 O4 52.33(12) . . ?
O30 Tm1 N3 90.74(12) . . ?
O7 Tm1 N3 105.93(13) . . ?
O2 Tm1 N3 170.06(12) . . ?
O20 Tm1 N3 92.90(12) . . ?
O6 Tm1 N3 105.73(12) . . ?
O1 Tm1 N3 67.28(12) . . ?
O3 Tm1 N3 26.18(12) . . ?
O4 Tm1 N3 26.34(12) . . ?
O20 S20 C21 105.9(2) . . ?
O20 S20 C20 103.7(3) . . ?
C21 S20 C20 99.1(4) . . ?
O30 S30 C31 104.6(3) . . ?
O30 S30 C30 103.2(2) . . ?
C31 S30 C30 97.8(3) . . ?
C1 O1 Tm1 138.6(3) . . ?
C1 O2 Tm1 143.9(3) 5_664 . ?
N3 O3 Tm1 96.0(3) . . ?
N3 O4 Tm1 95.5(3) . . ?
C6 O6 Tm1 126.2(3) . . ?
C6 O7 Tm1 160.7(3) 5_664 . ?
S20 O20 Tm1 134.78(19) . . ?
S30 O30 Tm1 126.33(18) . . ?
O5 N3 O3 122.7(4) . . ?
O5 N3 O4 121.9(5) . . ?
O3 N3 O4 115.4(4) . . ?
O5 N3 Tm1 172.2(4) . . ?
O3 N3 Tm1 57.8(2) . . ?
O4 N3 Tm1 58.2(2) . . ?
O2 C1 O1 128.2(4) 5_664 . ?
O2 C1 C2 116.2(4) 5_664 . ?
O1 C1 C2 115.5(4) . . ?
C3 C2 C4 116.4(4) . . ?
C3 C2 C1 120.4(3) . . ?
C4 C2 C1 123.1(4) . . ?
F3 C3 C8 118.3(4) . . ?
F3 C3 C2 119.7(4) . . ?
C8 C3 C2 121.9(4) . . ?
F4 C4 C5 119.1(4) . . ?
F4 C4 C2 119.1(4) . . ?
C5 C4 C2 121.7(4) . . ?
F5 C5 C7 119.8(4) . . ?
F5 C5 C4 118.3(4) . . ?
C7 C5 C4 121.9(4) . . ?
O7 C6 O6 126.9(4) 5_664 . ?
O7 C6 C7 115.9(4) 5_664 3_554 ?
O6 C6 C7 117.2(4) . 3_554 ?
C5 C7 C8 116.4(4) . . ?
C5 C7 C6 123.6(4) . 3_454 ?
C8 C7 C6 119.9(4) . 3_454 ?
F8 C8 C3 119.9(4) . . ?
F8 C8 C7 118.4(4) . . ?
C3 C8 C7 121.7(4) . . ?
S20 C20 H1 109.5 . . ?
S20 C20 H2 109.5 . . ?
H1 C20 H2 109.5 . . ?
S20 C20 H3 109.5 . . ?
H1 C20 H3 109.5 . . ?
H2 C20 H3 109.5 . . ?
S20 C21 H10A 109.5 . . ?
S20 C21 H10B 109.5 . . ?
H10A C21 H10B 109.5 . . ?
S20 C21 H10C 109.5 . . ?
H10A C21 H10C 109.5 . . ?
H10B C21 H10C 109.5 . . ?
S30 C30 H7 109.5 . . ?
S30 C30 H8 109.5 . . ?
H7 C30 H8 109.5 . . ?
S30 C30 H9 109.5 . . ?
H7 C30 H9 109.5 . . ?
H8 C30 H9 109.5 . . ?
S30 C31 H4 109.5 . . ?
S30 C31 H5 109.5 . . ?
H4 C31 H5 109.5 . . ?
S30 C31 H6 109.5 . . ?
H4 C31 H6 109.5 . . ?
H5 C31 H6 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
C21 S20 O20 Tm1 79.5(4) . . . . ?
C20 S20 O20 Tm1 -176.7(4) . . . . ?
C31 S30 O30 Tm1 -109.4(3) . . . . ?
C30 S30 O30 Tm1 148.8(3) . . . . ?
Tm1 O3 N3 O5 170.8(5) . . . . ?
Tm1 O3 N3 O4 -8.7(5) . . . . ?
Tm1 O4 N3 O5 -170.8(5) . . . . ?
Tm1 O4 N3 O3 8.7(5) . . . . ?
Tm1 O1 C1 O2 34.7(7) . . . 5_664 ?
Tm1 O1 C1 C2 -143.3(3) . . . . ?
O2 C1 C2 C3 -106.4(5) 5_664 . . . ?
O1 C1 C2 C3 71.8(5) . . . . ?
O2 C1 C2 C4 70.4(6) 5_664 . . . ?
O1 C1 C2 C4 -111.4(5) . . . . ?
C4 C2 C3 F3 -178.0(4) . . . . ?
C1 C2 C3 F3 -1.0(7) . . . . ?
C4 C2 C3 C8 1.7(7) . . . . ?
C1 C2 C3 C8 178.8(5) . . . . ?
C3 C2 C4 F4 -179.8(4) . . . . ?
C1 C2 C4 F4 3.3(7) . . . . ?
C3 C2 C4 C5 -1.1(7) . . . . ?
C1 C2 C4 C5 -178.1(4) . . . . ?
F4 C4 C5 F5 0.6(7) . . . . ?
C2 C4 C5 F5 -178.0(4) . . . . ?
F4 C4 C5 C7 178.6(4) . . . . ?
C2 C4 C5 C7 0.0(7) . . . . ?
Tm1 O6 C6 O7 11.0(6) . . . 5_664 ?
Tm1 O6 C6 C7 -167.3(3) . . . 3_554 ?
F5 C5 C7 C8 178.6(4) . . . . ?
C4 C5 C7 C8 0.6(7) . . . . ?
F5 C5 C7 C6 0.0(7) . . . 3_454 ?
C4 C5 C7 C6 -178.0(4) . . . 3_454 ?
F3 C3 C8 F8 0.8(7) . . . . ?
C2 C3 C8 F8 -179.0(4) . . . . ?
F3 C3 C8 C7 178.6(4) . . . . ?
C2 C3 C8 C7 -1.2(8) . . . . ?
C5 C7 C8 F8 177.8(4) . . . . ?
C6 C7 C8 F8 -3.5(7) 3_454 . . . ?
C5 C7 C8 C3 0.0(7) . . . . ?
C6 C7 C8 C3 178.6(4) 3_454 . . . ?

_refine_diff_density_max         0.700
_refine_diff_density_min         -1.590
_refine_diff_density_rms         0.133

_shelxl_version_number           2013-4


_exptl_crystal_recrystallization_method 'diffusion controlled crystallization'
