# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_4
_database_code_depnum_ccdc_archive 'CCDC 1568585'
_audit_update_record             
;
2017-08-12 deposited with the CCDC.
2017-09-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H14 Dy N3 O12'
_chemical_formula_weight         578.78

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

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

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

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

_cell_length_a                   13.9847(16)
_cell_length_b                   9.7770(12)
_cell_length_c                   17.2446(16)
_cell_angle_alpha                90
_cell_angle_beta                 127.437(6)
_cell_angle_gamma                90
_cell_volume                     1872.2(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    9968
_cell_measurement_theta_min      3.01
_cell_measurement_theta_max      27.54

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    2.053
_exptl_crystal_F_000             1124
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    4.063
_shelx_estimated_absorpt_T_min   0.687
_shelx_estimated_absorpt_T_max   0.737
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19646
_diffrn_reflns_av_unetI/netI     0.0230
_diffrn_reflns_av_R_equivalents  0.0327
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.776
_diffrn_reflns_theta_max         25.008
_diffrn_reflns_theta_full        25.008
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3310
_reflns_number_gt                2941
_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       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0235P)²+2.4379P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3310
_refine_ls_number_parameters     276
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0256
_refine_ls_R_factor_gt           0.0206
_refine_ls_wR_factor_ref         0.0499
_refine_ls_wR_factor_gt          0.0479
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_restrained_S_all      1.110
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Dy1 Dy 0.49112(2) -0.04325(2) 0.35079(2) 0.01700(6) Uani 1 1 d . . . . .
N1 N 0.9343(3) 0.7334(4) 0.8909(2) 0.0388(8) Uani 1 1 d . . . . .
H1 H 0.9806 0.7699 0.9496 0.047 Uiso 1 1 d R U . . .
N2 N 0.7442(3) 0.0215(4) 0.5040(3) 0.0401(8) Uani 1 1 d . . . . .
N3 N 1.0567(3) 0.7038(4) 0.6270(3) 0.0494(10) Uani 1 1 d . . . . .
O1 O 0.4927(2) 0.1629(2) 0.41548(17) 0.0266(5) Uani 1 1 d . . . . .
O2 O 0.5484(2) 0.1766(2) 0.56601(18) 0.0265(5) Uani 1 1 d . . . . .
O3 O 0.5982(2) 0.7698(2) 0.35819(16) 0.0212(5) Uani 1 1 d . . . . .
O4 O 0.5310(3) 0.5803(2) 0.27058(18) 0.0354(7) Uani 1 1 d . . . . .
O6 O 0.3511(2) -0.1928(3) 0.21452(18) 0.0355(6) Uani 1 1 d . . . . .
H6A H 0.2806 -0.1648 0.1869 0.053 Uiso 1 1 d R U . . .
H6B H 0.3648 -0.2511 0.1978 0.053 Uiso 1 1 d R U . . .
O7 O 0.6911(3) 0.0508(3) 0.4147(2) 0.0415(7) Uani 1 1 d . . . . .
O8 O 0.6816(2) -0.0402(3) 0.52318(19) 0.0330(6) Uani 1 1 d . . . . .
O9 O 0.2876(3) 0.0167(3) 0.2867(2) 0.0415(7) Uani 1 1 d . . . . .
H9B H 0.2900 0.0539 0.3319 0.062 Uiso 1 1 d R U . . .
H9A H 0.236(5) -0.041(5) 0.265(4) 0.060(17) Uiso 1 1 d . . . . .
O10 O 0.8486(3) 0.0502(5) 0.5672(3) 0.0949(16) Uani 1 1 d . . . . .
O11 O 0.9512(4) 0.7423(5) 0.5772(3) 0.0778(11) Uani 1 1 d . U . . .
O12 O 1.1147(3) 0.6877(4) 0.7156(2) 0.0667(11) Uani 1 1 d . . . . .
O13 O 1.1023(3) 0.6761(4) 0.5849(2) 0.0636(11) Uani 1 1 d . . . . .
C1 C 0.5414(3) 0.2232(3) 0.4953(2) 0.0177(7) Uani 1 1 d . . . . .
C2 C 0.5948(3) 0.3616(3) 0.5074(2) 0.0160(6) Uani 1 1 d . . . . .
C3 C 0.6653(3) 0.4225(3) 0.5988(2) 0.0182(7) Uani 1 1 d . . . . .
H3B H 0.6796 0.3764 0.6521 0.022 Uiso 1 1 calc R U . . .
C4 C 0.7152(3) 0.5524(3) 0.6118(2) 0.0172(7) Uani 1 1 d . . . . .
C5 C 0.6894(3) 0.6214(3) 0.5304(2) 0.0182(7) Uani 1 1 d . . . . .
H5A H 0.7206 0.7085 0.5378 0.022 Uiso 1 1 calc R U . . .
C6 C 0.6177(3) 0.5619(3) 0.4382(2) 0.0165(7) Uani 1 1 d . . . . .
C7 C 0.5718(3) 0.4306(3) 0.4271(2) 0.0175(7) Uani 1 1 d . . . . .
H7A H 0.5258 0.3892 0.3659 0.021 Uiso 1 1 calc R U . . .
C8 C 0.5819(3) 0.6424(3) 0.3503(2) 0.0185(7) Uani 1 1 d . . . . .
C9 C 0.7913(3) 0.6164(3) 0.7099(2) 0.0212(7) Uani 1 1 d . . . . .
C10 C 0.7755(4) 0.5860(4) 0.7802(3) 0.0398(10) Uani 1 1 d . . . . .
H10A H 0.7156 0.5253 0.7659 0.048 Uiso 1 1 calc R U . . .
C11 C 0.8480(4) 0.6455(5) 0.8703(3) 0.0507(13) Uani 1 1 d . . . . .
H11A H 0.8376 0.6252 0.9174 0.061 Uiso 1 1 calc R U . . .
C12 C 0.9534(3) 0.7677(4) 0.8262(3) 0.0299(8) Uani 1 1 d . . . . .
C13 C 0.8817(3) 0.7085(4) 0.7346(2) 0.0256(8) Uani 1 1 d . . . . .
H13A H 0.8940 0.7306 0.6888 0.031 Uiso 1 1 calc R U . . .
C14 C 1.0522(4) 0.8662(5) 0.8576(3) 0.0503(12) Uani 1 1 d . . . . .
H14A H 1.0909 0.8927 0.9241 0.075 Uiso 1 1 calc R U . . .
H14B H 1.0193 0.9457 0.8164 0.075 Uiso 1 1 calc R U . . .
H14C H 1.1099 0.8237 0.8523 0.075 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Dy1 O2 2.242(2) 3_656 ?
Dy1 O4 2.269(2) 2_645 ?
Dy1 O1 2.298(2) . ?
Dy1 O3 2.317(2) 1_545 ?
Dy1 O9 2.417(3) . ?
Dy1 O6 2.429(2) . ?
Dy1 O7 2.477(3) . ?
Dy1 O8 2.511(3) . ?
Dy1 N2 2.922(4) . ?
N1 C12 1.337(5) . ?
N1 C11 1.342(5) . ?
N1 H1 0.8800 . ?
N2 O10 1.210(5) . ?
N2 O8 1.262(4) . ?
N2 O7 1.271(5) . ?
N3 O12 1.229(4) . ?
N3 O11 1.231(5) . ?
N3 O13 1.252(5) . ?
O1 C1 1.251(4) . ?
O2 C1 1.249(4) . ?
O2 Dy1 2.242(2) 3_656 ?
O3 C8 1.259(4) . ?
O3 Dy1 2.317(2) 1_565 ?
O4 C8 1.256(4) . ?
O4 Dy1 2.269(2) 2_655 ?
O6 H6A 0.8386 . ?
O6 H6B 0.7153 . ?
O9 H9B 0.8408 . ?
O9 H9A 0.81(5) . ?
C1 C2 1.497(4) . ?
C2 C3 1.386(5) . ?
C2 C7 1.391(4) . ?
C3 C4 1.400(4) . ?
C3 H3B 0.9300 . ?
C4 C5 1.393(4) . ?
C4 C9 1.482(4) . ?
C5 C6 1.391(4) . ?
C5 H5A 0.9300 . ?
C6 C7 1.395(4) . ?
C6 C8 1.497(4) . ?
C7 H7A 0.9300 . ?
C9 C10 1.391(5) . ?
C9 C13 1.391(5) . ?
C10 C11 1.365(6) . ?
C10 H10A 0.9300 . ?
C11 H11A 0.9300 . ?
C12 C13 1.382(5) . ?
C12 C14 1.491(5) . ?
C13 H13A 0.9300 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 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
O2 Dy1 O4 162.04(10) 3_656 2_645 ?
O2 Dy1 O1 97.63(8) 3_656 . ?
O4 Dy1 O1 86.36(8) 2_645 . ?
O2 Dy1 O3 84.76(8) 3_656 1_545 ?
O4 Dy1 O3 101.07(9) 2_645 1_545 ?
O1 Dy1 O3 148.25(9) . 1_545 ?
O2 Dy1 O9 75.74(11) 3_656 . ?
O4 Dy1 O9 89.24(11) 2_645 . ?
O1 Dy1 O9 70.74(10) . . ?
O3 Dy1 O9 139.35(9) 1_545 . ?
O2 Dy1 O6 84.37(9) 3_656 . ?
O4 Dy1 O6 81.38(9) 2_645 . ?
O1 Dy1 O6 139.64(9) . . ?
O3 Dy1 O6 72.09(8) 1_545 . ?
O9 Dy1 O6 70.80(9) . . ?
O2 Dy1 O7 125.60(10) 3_656 . ?
O4 Dy1 O7 72.35(11) 2_645 . ?
O1 Dy1 O7 77.48(9) . . ?
O3 Dy1 O7 75.59(8) 1_545 . ?
O9 Dy1 O7 144.16(10) . . ?
O6 Dy1 O7 133.00(9) . . ?
O2 Dy1 O8 75.28(9) 3_656 . ?
O4 Dy1 O8 122.52(10) 2_645 . ?
O1 Dy1 O8 74.00(8) . . ?
O3 Dy1 O8 76.08(8) 1_545 . ?
O9 Dy1 O8 130.16(10) . . ?
O6 Dy1 O8 143.49(9) . . ?
O7 Dy1 O8 51.01(10) . . ?
O2 Dy1 N2 100.47(10) 3_656 . ?
O4 Dy1 N2 97.46(11) 2_645 . ?
O1 Dy1 N2 73.87(9) . . ?
O3 Dy1 N2 74.56(9) 1_545 . ?
O9 Dy1 N2 143.45(10) . . ?
O6 Dy1 N2 145.70(9) . . ?
O7 Dy1 N2 25.56(10) . . ?
O8 Dy1 N2 25.46(10) . . ?
C12 N1 C11 122.9(3) . . ?
C12 N1 H1 118.5 . . ?
C11 N1 H1 118.5 . . ?
O10 N2 O8 121.6(4) . . ?
O10 N2 O7 122.4(4) . . ?
O8 N2 O7 116.0(3) . . ?
O10 N2 Dy1 179.1(4) . . ?
O8 N2 Dy1 58.77(18) . . ?
O7 N2 Dy1 57.24(18) . . ?
O12 N3 O11 120.7(4) . . ?
O12 N3 O13 120.6(4) . . ?
O11 N3 O13 118.6(4) . . ?
C1 O1 Dy1 141.8(2) . . ?
C1 O2 Dy1 159.0(2) . 3_656 ?
C8 O3 Dy1 134.9(2) . 1_565 ?
C8 O4 Dy1 159.5(3) . 2_655 ?
Dy1 O6 H6A 109.4 . . ?
Dy1 O6 H6B 127.9 . . ?
H6A O6 H6B 122.7 . . ?
N2 O7 Dy1 97.2(2) . . ?
N2 O8 Dy1 95.8(2) . . ?
Dy1 O9 H9B 108.0 . . ?
Dy1 O9 H9A 121(4) . . ?
H9B O9 H9A 104.6 . . ?
O2 C1 O1 124.7(3) . . ?
O2 C1 C2 117.2(3) . . ?
O1 C1 C2 118.1(3) . . ?
C3 C2 C7 119.9(3) . . ?
C3 C2 C1 119.8(3) . . ?
C7 C2 C1 120.4(3) . . ?
C2 C3 C4 120.9(3) . . ?
C2 C3 H3B 119.6 . . ?
C4 C3 H3B 119.6 . . ?
C5 C4 C3 118.6(3) . . ?
C5 C4 C9 120.8(3) . . ?
C3 C4 C9 120.6(3) . . ?
C6 C5 C4 121.0(3) . . ?
C6 C5 H5A 119.5 . . ?
C4 C5 H5A 119.5 . . ?
C5 C6 C7 119.6(3) . . ?
C5 C6 C8 120.2(3) . . ?
C7 C6 C8 120.1(3) . . ?
C2 C7 C6 120.0(3) . . ?
C2 C7 H7A 120.0 . . ?
C6 C7 H7A 120.0 . . ?
O4 C8 O3 122.7(3) . . ?
O4 C8 C6 118.2(3) . . ?
O3 C8 C6 119.0(3) . . ?
C10 C9 C13 117.9(3) . . ?
C10 C9 C4 121.4(3) . . ?
C13 C9 C4 120.8(3) . . ?
C11 C10 C9 120.0(4) . . ?
C11 C10 H10A 120.0 . . ?
C9 C10 H10A 120.0 . . ?
N1 C11 C10 120.0(4) . . ?
N1 C11 H11A 120.0 . . ?
C10 C11 H11A 120.0 . . ?
N1 C12 C13 118.3(3) . . ?
N1 C12 C14 118.0(3) . . ?
C13 C12 C14 123.6(4) . . ?
C12 C13 C9 121.0(3) . . ?
C12 C13 H13A 119.5 . . ?
C9 C13 H13A 119.5 . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 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
O10 N2 O7 Dy1 -179.0(4) . . . . ?
O8 N2 O7 Dy1 1.2(3) . . . . ?
O10 N2 O8 Dy1 179.0(4) . . . . ?
O7 N2 O8 Dy1 -1.2(3) . . . . ?
Dy1 O2 C1 O1 -16.2(8) 3_656 . . . ?
Dy1 O2 C1 C2 163.4(5) 3_656 . . . ?
Dy1 O1 C1 O2 -50.9(5) . . . . ?
Dy1 O1 C1 C2 129.5(3) . . . . ?
O2 C1 C2 C3 10.2(4) . . . . ?
O1 C1 C2 C3 -170.2(3) . . . . ?
O2 C1 C2 C7 -168.4(3) . . . . ?
O1 C1 C2 C7 11.3(4) . . . . ?
C7 C2 C3 C4 -0.7(5) . . . . ?
C1 C2 C3 C4 -179.3(3) . . . . ?
C2 C3 C4 C5 2.0(5) . . . . ?
C2 C3 C4 C9 -179.4(3) . . . . ?
C3 C4 C5 C6 -1.3(5) . . . . ?
C9 C4 C5 C6 -179.9(3) . . . . ?
C4 C5 C6 C7 -0.6(5) . . . . ?
C4 C5 C6 C8 174.4(3) . . . . ?
C3 C2 C7 C6 -1.2(5) . . . . ?
C1 C2 C7 C6 177.3(3) . . . . ?
C5 C6 C7 C2 1.9(5) . . . . ?
C8 C6 C7 C2 -173.2(3) . . . . ?
Dy1 O4 C8 O3 96.5(7) 2_655 . . . ?
Dy1 O4 C8 C6 -87.2(7) 2_655 . . . ?
Dy1 O3 C8 O4 92.2(4) 1_565 . . . ?
Dy1 O3 C8 C6 -84.1(4) 1_565 . . . ?
C5 C6 C8 O4 170.6(3) . . . . ?
C7 C6 C8 O4 -14.3(5) . . . . ?
C5 C6 C8 O3 -12.9(5) . . . . ?
C7 C6 C8 O3 162.2(3) . . . . ?
C5 C4 C9 C10 150.0(4) . . . . ?
C3 C4 C9 C10 -28.6(5) . . . . ?
C5 C4 C9 C13 -30.4(5) . . . . ?
C3 C4 C9 C13 151.1(3) . . . . ?
C13 C9 C10 C11 -0.4(6) . . . . ?
C4 C9 C10 C11 179.3(4) . . . . ?
C12 N1 C11 C10 0.5(8) . . . . ?
C9 C10 C11 N1 0.1(8) . . . . ?
C11 N1 C12 C13 -0.8(6) . . . . ?
C11 N1 C12 C14 -179.9(5) . . . . ?
N1 C12 C13 C9 0.5(6) . . . . ?
C14 C12 C13 C9 179.5(4) . . . . ?
C10 C9 C13 C12 0.1(6) . . . . ?
C4 C9 C13 C12 -179.6(3) . . . . ?

_refine_diff_density_max         0.982
_refine_diff_density_min         -0.895
_refine_diff_density_rms         0.106

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

data_4_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1568591'
_audit_update_record             
;
2017-08-12 deposited with the CCDC.
2017-09-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H14 N3 O12 Tb'
_chemical_formula_weight         575.21

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'
Tb Tb -0.1723 4.1537 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   13.9460(16)
_cell_length_b                   9.8277(12)
_cell_length_c                   17.3048(16)
_cell_angle_alpha                90
_cell_angle_beta                 127.674(6)
_cell_angle_gamma                90
_cell_volume                     1877.2(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    9128
_cell_measurement_theta_min      3.14
_cell_measurement_theta_max      27.45

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    2.035
_exptl_crystal_F_000             1120
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    3.839
_shelx_estimated_absorpt_T_min   0.700
_shelx_estimated_absorpt_T_max   0.749
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            35209
_diffrn_reflns_av_unetI/netI     0.0479
_diffrn_reflns_av_R_equivalents  0.0826
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.974
_diffrn_reflns_theta_max         27.551
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4324
_reflns_number_gt                3354
_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       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0187P)²+2.3450P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4324
_refine_ls_number_parameters     272
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0556
_refine_ls_R_factor_gt           0.0317
_refine_ls_wR_factor_ref         0.0546
_refine_ls_wR_factor_gt          0.0498
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_restrained_S_all      1.024
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Tb1 Tb -0.50848(2) -0.04312(2) -0.64889(2) 0.01591(6) Uani 1 1 d . . . . .
O1 O -0.4005(2) -0.2318(2) -0.64095(18) 0.0184(6) Uani 1 1 d . . . . .
O2 O -0.4710(3) -0.4196(3) -0.72936(19) 0.0314(8) Uani 1 1 d . . . . .
O3 O -0.5075(3) -0.8352(3) -0.58514(18) 0.0242(6) Uani 1 1 d . . . . .
O4 O -0.4510(3) -0.8219(3) -0.43441(19) 0.0230(6) Uani 1 1 d . . . . .
O6 O -0.6504(3) -0.1930(3) -0.78694(19) 0.0326(7) Uani 1 1 d . . . . .
H6A H -0.7216 -0.1653 -0.8150 0.049 Uiso 1 1 d R U . . .
H6B H -0.6369 -0.2514 -0.8038 0.049 Uiso 1 1 d R U . . .
O7 O -0.3044(3) 0.0509(3) -0.5818(2) 0.0381(8) Uani 1 1 d . . . . .
O8 O -0.3169(3) -0.0404(3) -0.47527(19) 0.0294(6) Uani 1 1 d . . . . .
O9 O -0.7150(3) 0.0152(3) -0.7135(2) 0.0361(8) Uani 1 1 d . . . . .
H9A H -0.7572 -0.0558 -0.7325 0.054 Uiso 1 1 d R U . . .
H9B H -0.7122 0.0526 -0.6680 0.054 Uiso 1 1 d R U . . .
O10 O -0.1486(3) 0.0508(5) -0.4287(3) 0.0882(15) Uani 1 1 d . . . . .
O11 O -0.0513(4) -0.2570(6) -0.4243(3) 0.0873(17) Uani 1 1 d . . . . .
O12 O 0.1138(3) -0.3105(4) -0.2851(2) 0.0593(11) Uani 1 1 d . . . . .
O13 O 0.1011(3) -0.3226(4) -0.4156(2) 0.0564(11) Uani 1 1 d . . . . .
N1 N -0.0670(3) -0.2671(4) -0.1100(2) 0.0323(9) Uani 1 1 d . . . . .
H1 H -0.0209 -0.2309 -0.0513 0.039 Uiso 1 1 d R U . . .
N2 N -0.2533(4) 0.0211(4) -0.4932(3) 0.0383(10) Uani 1 1 d . . . . .
N3 N 0.0540(4) -0.2949(5) -0.3747(3) 0.0462(11) Uani 1 1 d . . . . .
C1 C -0.4179(3) -0.3572(4) -0.6490(3) 0.0163(8) Uani 1 1 d . . . . .
C2 C -0.3827(3) -0.4382(4) -0.5617(2) 0.0138(7) Uani 1 1 d . . . . .
C3 C -0.4278(3) -0.5686(3) -0.5726(2) 0.0152(8) Uani 1 1 d . . . . .
H3A H -0.4735 -0.6100 -0.6336 0.018 Uiso 1 1 calc R U . . .
C4 C -0.4050(3) -0.6370(4) -0.4933(3) 0.0143(7) Uani 1 1 d . . . . .
C5 C -0.3340(3) -0.5772(3) -0.4014(3) 0.0152(8) Uani 1 1 d . . . . .
H5B H -0.3190 -0.6236 -0.3481 0.018 Uiso 1 1 calc R U . . .
C6 C -0.2850(3) -0.4473(4) -0.3887(2) 0.0139(7) Uani 1 1 d . . . . .
C7 C -0.3102(3) -0.3782(4) -0.4694(2) 0.0140(7) Uani 1 1 d . . . . .
H7A H -0.2787 -0.2916 -0.4618 0.017 Uiso 1 1 calc R U . . .
C8 C -0.4582(3) -0.7749(4) -0.5052(3) 0.0156(8) Uani 1 1 d . . . . .
C9 C -0.2086(3) -0.3837(4) -0.2902(2) 0.0171(8) Uani 1 1 d . . . . .
C10 C -0.2248(4) -0.4153(5) -0.2205(3) 0.0334(11) Uani 1 1 d . . . . .
H10A H -0.2841 -0.4771 -0.2348 0.040 Uiso 1 1 calc R U . . .
C11 C -0.1527(4) -0.3547(6) -0.1309(3) 0.0427(13) Uani 1 1 d . . . . .
H11A H -0.1635 -0.3748 -0.0842 0.051 Uiso 1 1 calc R U . . .
C12 C -0.0475(4) -0.2313(4) -0.1740(3) 0.0248(9) Uani 1 1 d . . . . .
C13 C -0.1188(3) -0.2912(4) -0.2654(3) 0.0208(9) Uani 1 1 d . . . . .
H13A H -0.1063 -0.2691 -0.3108 0.025 Uiso 1 1 calc R U . . .
C14 C 0.0511(4) -0.1332(5) -0.1425(4) 0.0463(13) Uani 1 1 d . . . . .
H14A H 0.1021 -0.1236 -0.0728 0.069 Uiso 1 1 calc R U . . .
H14B H 0.0166 -0.0464 -0.1725 0.069 Uiso 1 1 calc R U . . .
H14C H 0.0983 -0.1660 -0.1620 0.069 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Tb1 O4 2.270(3) 3_444 ?
Tb1 O2 2.293(3) 2_453 ?
Tb1 O3 2.318(3) 1_565 ?
Tb1 O1 2.339(3) . ?
Tb1 O9 2.437(3) . ?
Tb1 O6 2.453(3) . ?
Tb1 O7 2.502(3) . ?
Tb1 O8 2.521(3) . ?
Tb1 N2 2.933(4) . ?
O1 C1 1.248(4) . ?
O2 C1 1.265(4) . ?
O2 Tb1 2.293(3) 2_443 ?
O3 C8 1.255(4) . ?
O3 Tb1 2.318(2) 1_545 ?
O4 C8 1.255(4) . ?
O4 Tb1 2.270(2) 3_444 ?
O6 H6A 0.8401 . ?
O6 H6B 0.7185 . ?
O7 N2 1.268(5) . ?
O8 N2 1.258(5) . ?
O9 H9A 0.8400 . ?
O9 H9B 0.8477 . ?
O10 N2 1.213(5) . ?
O11 N3 1.221(5) . ?
O12 N3 1.241(5) . ?
O13 N3 1.256(5) . ?
N1 C11 1.331(6) . ?
N1 C12 1.338(5) . ?
N1 H1 0.8800 . ?
C1 C2 1.500(5) . ?
C2 C3 1.388(5) . ?
C2 C7 1.395(5) . ?
C3 C4 1.380(5) . ?
C3 H3A 0.9300 . ?
C4 C5 1.389(5) . ?
C4 C8 1.497(5) . ?
C5 C6 1.401(5) . ?
C5 H5B 0.9300 . ?
C6 C7 1.390(5) . ?
C6 C9 1.488(5) . ?
C7 H7A 0.9300 . ?
C9 C13 1.386(5) . ?
C9 C10 1.391(5) . ?
C10 C11 1.365(6) . ?
C10 H10A 0.9300 . ?
C11 H11A 0.9300 . ?
C12 C13 1.383(5) . ?
C12 C14 1.484(6) . ?
C13 H13A 0.9300 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 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
O4 Tb1 O2 162.41(11) 3_444 2_453 ?
O4 Tb1 O3 98.30(9) 3_444 1_565 ?
O2 Tb1 O3 86.09(9) 2_453 1_565 ?
O4 Tb1 O1 84.30(9) 3_444 . ?
O2 Tb1 O1 100.82(9) 2_453 . ?
O3 Tb1 O1 148.69(9) 1_565 . ?
O4 Tb1 O9 75.26(10) 3_444 . ?
O2 Tb1 O9 90.31(11) 2_453 . ?
O3 Tb1 O9 70.88(10) 1_565 . ?
O1 Tb1 O9 138.72(10) . . ?
O4 Tb1 O6 84.35(10) 3_444 . ?
O2 Tb1 O6 81.36(10) 2_453 . ?
O3 Tb1 O6 139.42(10) 1_565 . ?
O1 Tb1 O6 71.85(9) . . ?
O9 Tb1 O6 70.77(10) . . ?
O4 Tb1 O7 125.10(10) 3_444 . ?
O2 Tb1 O7 72.46(11) 2_453 . ?
O3 Tb1 O7 77.25(10) 1_565 . ?
O1 Tb1 O7 75.92(10) . . ?
O9 Tb1 O7 144.69(10) . . ?
O6 Tb1 O7 133.30(10) . . ?
O4 Tb1 O8 75.12(10) 3_444 . ?
O2 Tb1 O8 122.38(11) 2_453 . ?
O3 Tb1 O8 74.33(10) 1_565 . ?
O1 Tb1 O8 76.28(9) . . ?
O9 Tb1 O8 129.71(10) . . ?
O6 Tb1 O8 143.50(10) . . ?
O7 Tb1 O8 50.69(10) . . ?
O4 Tb1 N2 100.11(11) 3_444 . ?
O2 Tb1 N2 97.47(12) 2_453 . ?
O3 Tb1 N2 73.86(10) 1_565 . ?
O1 Tb1 N2 74.97(10) . . ?
O9 Tb1 N2 143.22(10) . . ?
O6 Tb1 N2 145.89(10) . . ?
O7 Tb1 N2 25.44(10) . . ?
O8 Tb1 N2 25.26(10) . . ?
C1 O1 Tb1 134.6(2) . . ?
C1 O2 Tb1 158.0(3) . 2_443 ?
C8 O3 Tb1 141.3(2) . 1_545 ?
C8 O4 Tb1 158.9(2) . 3_444 ?
Tb1 O6 H6A 109.5 . . ?
Tb1 O6 H6B 128.2 . . ?
H6A O6 H6B 122.3 . . ?
N2 O7 Tb1 96.6(2) . . ?
N2 O8 Tb1 96.0(2) . . ?
Tb1 O9 H9A 109.5 . . ?
Tb1 O9 H9B 107.8 . . ?
H9A O9 H9B 110.3 . . ?
C11 N1 C12 123.2(4) . . ?
C11 N1 H1 118.4 . . ?
C12 N1 H1 118.4 . . ?
O10 N2 O8 121.5(5) . . ?
O10 N2 O7 121.9(5) . . ?
O8 N2 O7 116.7(4) . . ?
O10 N2 Tb1 178.5(4) . . ?
O8 N2 Tb1 58.7(2) . . ?
O7 N2 Tb1 57.9(2) . . ?
O11 N3 O12 121.2(4) . . ?
O11 N3 O13 119.2(4) . . ?
O12 N3 O13 119.5(4) . . ?
O1 C1 O2 123.0(3) . . ?
O1 C1 C2 119.4(3) . . ?
O2 C1 C2 117.5(3) . . ?
C3 C2 C7 119.7(3) . . ?
C3 C2 C1 120.7(3) . . ?
C7 C2 C1 119.4(3) . . ?
C4 C3 C2 120.3(3) . . ?
C4 C3 H3A 119.8 . . ?
C2 C3 H3A 119.8 . . ?
C3 C4 C5 120.1(3) . . ?
C3 C4 C8 120.7(3) . . ?
C5 C4 C8 119.2(3) . . ?
C4 C5 C6 120.2(3) . . ?
C4 C5 H5B 119.9 . . ?
C6 C5 H5B 119.9 . . ?
C7 C6 C5 119.2(3) . . ?
C7 C6 C9 120.7(3) . . ?
C5 C6 C9 120.1(3) . . ?
C6 C7 C2 120.3(3) . . ?
C6 C7 H7A 119.8 . . ?
C2 C7 H7A 119.8 . . ?
O3 C8 O4 124.4(3) . . ?
O3 C8 C4 118.1(3) . . ?
O4 C8 C4 117.5(3) . . ?
C13 C9 C10 118.2(3) . . ?
C13 C9 C6 120.6(3) . . ?
C10 C9 C6 121.2(3) . . ?
C11 C10 C9 119.4(4) . . ?
C11 C10 H10A 120.3 . . ?
C9 C10 H10A 120.3 . . ?
N1 C11 C10 120.4(4) . . ?
N1 C11 H11A 119.8 . . ?
C10 C11 H11A 119.8 . . ?
N1 C12 C13 117.8(4) . . ?
N1 C12 C14 118.6(4) . . ?
C13 C12 C14 123.6(4) . . ?
C12 C13 C9 121.1(4) . . ?
C12 C13 H13A 119.5 . . ?
C9 C13 H13A 119.5 . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 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
Tb1 O8 N2 O10 178.2(4) . . . . ?
Tb1 O8 N2 O7 -1.5(4) . . . . ?
Tb1 O7 N2 O10 -178.2(4) . . . . ?
Tb1 O7 N2 O8 1.5(4) . . . . ?
Tb1 O1 C1 O2 91.3(4) . . . . ?
Tb1 O1 C1 C2 -84.3(4) . . . . ?
Tb1 O2 C1 O1 94.9(7) 2_443 . . . ?
Tb1 O2 C1 C2 -89.4(7) 2_443 . . . ?
O1 C1 C2 C3 163.3(3) . . . . ?
O2 C1 C2 C3 -12.6(5) . . . . ?
O1 C1 C2 C7 -12.5(5) . . . . ?
O2 C1 C2 C7 171.7(3) . . . . ?
C7 C2 C3 C4 2.4(5) . . . . ?
C1 C2 C3 C4 -173.3(3) . . . . ?
C2 C3 C4 C5 -1.7(5) . . . . ?
C2 C3 C4 C8 177.0(3) . . . . ?
C3 C4 C5 C6 -0.1(5) . . . . ?
C8 C4 C5 C6 -178.9(3) . . . . ?
C4 C5 C6 C7 1.3(5) . . . . ?
C4 C5 C6 C9 -179.8(3) . . . . ?
C5 C6 C7 C2 -0.6(5) . . . . ?
C9 C6 C7 C2 -179.5(3) . . . . ?
C3 C2 C7 C6 -1.2(5) . . . . ?
C1 C2 C7 C6 174.6(3) . . . . ?
Tb1 O3 C8 O4 -50.4(6) 1_545 . . . ?
Tb1 O3 C8 C4 129.9(3) 1_545 . . . ?
Tb1 O4 C8 O3 -16.7(10) 3_444 . . . ?
Tb1 O4 C8 C4 162.9(5) 3_444 . . . ?
C3 C4 C8 O3 11.1(5) . . . . ?
C5 C4 C8 O3 -170.2(3) . . . . ?
C3 C4 C8 O4 -168.6(3) . . . . ?
C5 C4 C8 O4 10.2(5) . . . . ?
C7 C6 C9 C13 -29.8(5) . . . . ?
C5 C6 C9 C13 151.3(4) . . . . ?
C7 C6 C9 C10 150.4(4) . . . . ?
C5 C6 C9 C10 -28.5(5) . . . . ?
C13 C9 C10 C11 0.1(7) . . . . ?
C6 C9 C10 C11 179.9(4) . . . . ?
C12 N1 C11 C10 1.3(8) . . . . ?
C9 C10 C11 N1 -0.6(8) . . . . ?
C11 N1 C12 C13 -1.5(7) . . . . ?
C11 N1 C12 C14 -179.7(5) . . . . ?
N1 C12 C13 C9 1.0(6) . . . . ?
C14 C12 C13 C9 179.1(4) . . . . ?
C10 C9 C13 C12 -0.3(6) . . . . ?
C6 C9 C13 C12 179.9(4) . . . . ?

_refine_diff_density_max         0.602
_refine_diff_density_min         -0.684
_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_5
_database_code_depnum_ccdc_archive 'CCDC 1568588'
_audit_update_record             
;
2017-08-12 deposited with the CCDC.
2017-09-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H14 Ho N3 O12'
_chemical_formula_weight         581.21

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'
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'

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

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

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

_cell_length_a                   13.9924(16)
_cell_length_b                   9.7500(12)
_cell_length_c                   17.2189(16)
_cell_angle_alpha                90
_cell_angle_beta                 127.460(6)
_cell_angle_gamma                90
_cell_volume                     1864.7(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    9939
_cell_measurement_theta_min      2.98
_cell_measurement_theta_max      27.50

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    2.070
_exptl_crystal_F_000             1128
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    4.316
_shelx_estimated_absorpt_T_min   0.672
_shelx_estimated_absorpt_T_max   0.724
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            29449
_diffrn_reflns_av_unetI/netI     0.0248
_diffrn_reflns_av_R_equivalents  0.0504
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.780
_diffrn_reflns_theta_max         25.009
_diffrn_reflns_theta_full        25.009
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3298
_reflns_number_gt                2818
_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       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0199P)²+1.9422P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3298
_refine_ls_number_parameters     281
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0308
_refine_ls_R_factor_gt           0.0211
_refine_ls_wR_factor_ref         0.0452
_refine_ls_wR_factor_gt          0.0424
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.039
_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 -0.50869(2) -0.04343(2) -0.64922(2) 0.01845(6) Uani 1 1 d . . . . .
O1 O -0.4026(2) -0.2301(2) -0.64212(17) 0.0226(5) Uani 1 1 d . . . . .
O2 O -0.4687(3) -0.4199(3) -0.72957(19) 0.0391(8) Uani 1 1 d . . . . .
O3 O -0.5067(2) -0.8383(2) -0.58459(17) 0.0276(6) Uani 1 1 d . . . . .
O4 O -0.4520(2) -0.8239(2) -0.43392(18) 0.0277(6) Uani 1 1 d . . . . .
O6 O -0.6479(2) -0.1923(3) -0.78470(19) 0.0384(7) Uani 1 1 d . . . . .
H6A H -0.7169 -0.1650 -0.8117 0.058 Uiso 1 1 d R U . . .
H6B H -0.6344 -0.2506 -0.8015 0.058 Uiso 1 1 d R U . . .
O7 O -0.3102(3) 0.0505(3) -0.5868(2) 0.0428(7) Uani 1 1 d . . . . .
O8 O -0.3193(2) -0.0410(3) -0.47768(19) 0.0342(6) Uani 1 1 d . . . . .
O9 O -0.7108(3) 0.0172(3) -0.7137(2) 0.0450(8) Uani 1 1 d . . . . .
H9A H -0.7524 -0.0522 -0.7324 0.067 Uiso 1 1 d R U . . .
H9B H -0.7081 0.0546 -0.6683 0.067 Uiso 1 1 d R U . . .
O10 O -0.1521(3) 0.0491(5) -0.4346(3) 0.0970(16) Uani 1 1 d . . . . .
O11 O -0.0542(11) -0.2885(10) -0.4297(9) 0.064(4) Uani 0.5 1 d . U P . .
O11' O -0.0388(8) -0.2287(11) -0.4139(6) 0.058(3) Uani 0.5 1 d . . P . .
O12 O 0.1155(3) -0.3147(4) -0.2834(2) 0.0718(12) Uani 1 1 d . . . . .
O13 O 0.1039(3) -0.3238(5) -0.4141(2) 0.0714(12) Uani 1 1 d . . . . .
N1 N -0.0658(3) -0.2669(4) -0.1087(2) 0.0435(10) Uani 1 1 d . . . . .
H1 H -0.0208 -0.2310 -0.0512 0.052 Uiso 1 1 d R U . . .
N2 N -0.2567(3) 0.0208(4) -0.4973(3) 0.0438(9) Uani 1 1 d . . . . .
N3 N 0.0573(4) -0.2971(5) -0.3722(3) 0.0536(11) Uani 1 1 d . . . . .
C1 C -0.4179(3) -0.3576(4) -0.6498(2) 0.0207(8) Uani 1 1 d . . . . .
C2 C -0.3832(3) -0.4387(3) -0.5621(2) 0.0182(7) Uani 1 1 d . . . . .
C3 C -0.4281(3) -0.5699(3) -0.5728(2) 0.0191(8) Uani 1 1 d . . . . .
H3A H -0.4738 -0.6119 -0.6339 0.023 Uiso 1 1 calc R U . . .
C4 C -0.4050(3) -0.6384(3) -0.4925(2) 0.0163(7) Uani 1 1 d . . . . .
C5 C -0.3346(3) -0.5779(3) -0.4010(2) 0.0194(8) Uani 1 1 d . . . . .
H5B H -0.3203 -0.6240 -0.3476 0.023 Uiso 1 1 calc R U . . .
C6 C -0.2848(3) -0.4480(4) -0.3883(2) 0.0185(7) Uani 1 1 d . . . . .
C7 C -0.3103(3) -0.3789(4) -0.4696(2) 0.0185(7) Uani 1 1 d . . . . .
H7A H -0.2784 -0.2920 -0.4621 0.022 Uiso 1 1 calc R U . . .
C8 C -0.4584(3) -0.7777(3) -0.5047(2) 0.0178(7) Uani 1 1 d . . . . .
C9 C -0.2090(3) -0.3843(4) -0.2899(2) 0.0222(8) Uani 1 1 d . . . . .
C10 C -0.2243(4) -0.4139(5) -0.2194(3) 0.0414(11) Uani 1 1 d . . . . .
H10A H -0.2842 -0.4746 -0.2335 0.050 Uiso 1 1 calc R U . . .
C11 C -0.1510(4) -0.3536(6) -0.1289(3) 0.0563(14) Uani 1 1 d . . . . .
H11A H -0.1612 -0.3738 -0.0816 0.068 Uiso 1 1 calc R U . . .
C12 C -0.0462(4) -0.2320(4) -0.1738(3) 0.0329(10) Uani 1 1 d . . . . .
C13 C -0.1186(3) -0.2912(4) -0.2652(3) 0.0280(9) Uani 1 1 d . . . . .
H13A H -0.1071 -0.2687 -0.3114 0.034 Uiso 1 1 calc R U . . .
C14 C 0.0525(4) -0.1346(5) -0.1427(4) 0.0554(13) Uani 1 1 d . . . . .
H14A H 0.0728 -0.0840 -0.0867 0.083 Uiso 1 1 calc R U . . .
H14B H 0.0269 -0.0721 -0.1952 0.083 Uiso 1 1 calc R U . . .
H14C H 0.1218 -0.1845 -0.1261 0.083 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 O4 2.232(2) 3_444 ?
Ho1 O2 2.259(2) 2_453 ?
Ho1 O3 2.281(2) 1_565 ?
Ho1 O1 2.304(2) . ?
Ho1 O9 2.400(3) . ?
Ho1 O6 2.411(3) . ?
Ho1 O7 2.465(3) . ?
Ho1 O8 2.495(3) . ?
Ho1 N2 2.907(4) . ?
O1 C1 1.255(4) . ?
O2 C1 1.254(4) . ?
O2 Ho1 2.259(2) 2_443 ?
O3 C8 1.252(4) . ?
O3 Ho1 2.281(2) 1_545 ?
O4 C8 1.250(4) . ?
O4 Ho1 2.232(2) 3_444 ?
O6 H6A 0.8199 . ?
O6 H6B 0.7142 . ?
O7 N2 1.271(5) . ?
O8 N2 1.267(5) . ?
O9 H9A 0.8201 . ?
O9 H9B 0.8429 . ?
O10 N2 1.208(5) . ?
O11 O11' 0.624(15) . ?
O11 N3 1.242(13) . ?
O11' N3 1.263(9) . ?
O12 N3 1.231(5) . ?
O13 N3 1.260(5) . ?
N1 C11 1.324(6) . ?
N1 C12 1.350(5) . ?
N1 H1 0.8601 . ?
C1 C2 1.499(5) . ?
C2 C3 1.388(5) . ?
C2 C7 1.394(5) . ?
C3 C4 1.385(5) . ?
C3 H3A 0.9300 . ?
C4 C5 1.382(5) . ?
C4 C8 1.502(5) . ?
C5 C6 1.396(5) . ?
C5 H5B 0.9300 . ?
C6 C7 1.390(5) . ?
C6 C9 1.481(5) . ?
C7 H7A 0.9300 . ?
C9 C10 1.385(5) . ?
C9 C13 1.396(5) . ?
C10 C11 1.372(6) . ?
C10 H10A 0.9300 . ?
C11 H11A 0.9300 . ?
C12 C13 1.377(5) . ?
C12 C14 1.483(6) . ?
C13 H13A 0.9300 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 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
O4 Ho1 O2 161.94(11) 3_444 2_453 ?
O4 Ho1 O3 97.47(9) 3_444 1_565 ?
O2 Ho1 O3 86.35(9) 2_453 1_565 ?
O4 Ho1 O1 84.86(9) 3_444 . ?
O2 Ho1 O1 101.19(9) 2_453 . ?
O3 Ho1 O1 148.26(9) 1_565 . ?
O4 Ho1 O9 76.05(10) 3_444 . ?
O2 Ho1 O9 88.71(11) 2_453 . ?
O3 Ho1 O9 70.80(10) 1_565 . ?
O1 Ho1 O9 139.36(9) . . ?
O4 Ho1 O6 84.41(10) 3_444 . ?
O2 Ho1 O6 81.40(10) 2_453 . ?
O3 Ho1 O6 139.70(9) 1_565 . ?
O1 Ho1 O6 72.02(9) . . ?
O9 Ho1 O6 70.69(10) . . ?
O4 Ho1 O7 125.98(10) 3_444 . ?
O2 Ho1 O7 72.07(11) 2_453 . ?
O3 Ho1 O7 77.61(10) 1_565 . ?
O1 Ho1 O7 75.61(9) . . ?
O9 Ho1 O7 143.94(10) . . ?
O6 Ho1 O7 132.71(10) . . ?
O4 Ho1 O8 75.22(10) 3_444 . ?
O2 Ho1 O8 122.66(10) 2_453 . ?
O3 Ho1 O8 74.05(9) 1_565 . ?
O1 Ho1 O8 76.03(9) . . ?
O9 Ho1 O8 130.52(10) . . ?
O6 Ho1 O8 143.35(9) . . ?
O7 Ho1 O8 51.44(10) . . ?
O4 Ho1 N2 100.66(11) 3_444 . ?
O2 Ho1 N2 97.36(12) 2_453 . ?
O3 Ho1 N2 73.96(10) 1_565 . ?
O1 Ho1 N2 74.50(9) . . ?
O9 Ho1 N2 143.75(10) . . ?
O6 Ho1 N2 145.53(10) . . ?
O7 Ho1 N2 25.74(10) . . ?
O8 Ho1 N2 25.71(10) . . ?
C1 O1 Ho1 135.6(2) . . ?
C1 O2 Ho1 159.6(3) . 2_443 ?
C8 O3 Ho1 142.0(2) . 1_545 ?
C8 O4 Ho1 159.1(2) . 3_444 ?
Ho1 O6 H6A 109.5 . . ?
Ho1 O6 H6B 127.9 . . ?
H6A O6 H6B 122.6 . . ?
N2 O7 Ho1 96.9(2) . . ?
N2 O8 Ho1 95.6(2) . . ?
Ho1 O9 H9A 109.5 . . ?
Ho1 O9 H9B 107.5 . . ?
H9A O9 H9B 110.0 . . ?
O11' O11 N3 77.5(17) . . ?
O11 O11' N3 73.7(16) . . ?
C11 N1 C12 123.2(4) . . ?
C11 N1 H1 118.4 . . ?
C12 N1 H1 118.4 . . ?
O10 N2 O8 121.9(4) . . ?
O10 N2 O7 122.1(4) . . ?
O8 N2 O7 116.0(3) . . ?
O10 N2 Ho1 179.2(4) . . ?
O8 N2 Ho1 58.69(19) . . ?
O7 N2 Ho1 57.35(19) . . ?
O12 N3 O11 124.1(7) . . ?
O12 N3 O13 120.1(4) . . ?
O11 N3 O13 113.2(7) . . ?
O12 N3 O11' 116.8(6) . . ?
O11 N3 O11' 28.8(7) . . ?
O13 N3 O11' 121.8(5) . . ?
O2 C1 O1 122.8(3) . . ?
O2 C1 C2 117.9(3) . . ?
O1 C1 C2 119.1(3) . . ?
C3 C2 C7 119.6(3) . . ?
C3 C2 C1 120.6(3) . . ?
C7 C2 C1 119.7(3) . . ?
C4 C3 C2 120.0(3) . . ?
C4 C3 H3A 120.0 . . ?
C2 C3 H3A 120.0 . . ?
C5 C4 C3 120.2(3) . . ?
C5 C4 C8 119.6(3) . . ?
C3 C4 C8 120.1(3) . . ?
C4 C5 C6 120.5(3) . . ?
C4 C5 H5B 119.7 . . ?
C6 C5 H5B 119.7 . . ?
C7 C6 C5 118.9(3) . . ?
C7 C6 C9 121.0(3) . . ?
C5 C6 C9 120.1(3) . . ?
C6 C7 C2 120.7(3) . . ?
C6 C7 H7A 119.7 . . ?
C2 C7 H7A 119.7 . . ?
O4 C8 O3 124.8(3) . . ?
O4 C8 C4 117.1(3) . . ?
O3 C8 C4 118.1(3) . . ?
C10 C9 C13 117.5(3) . . ?
C10 C9 C6 122.0(3) . . ?
C13 C9 C6 120.5(3) . . ?
C11 C10 C9 120.0(4) . . ?
C11 C10 H10A 120.0 . . ?
C9 C10 H10A 120.0 . . ?
N1 C11 C10 120.3(4) . . ?
N1 C11 H11A 119.9 . . ?
C10 C11 H11A 119.9 . . ?
N1 C12 C13 117.6(4) . . ?
N1 C12 C14 118.4(4) . . ?
C13 C12 C14 123.9(4) . . ?
C12 C13 C9 121.4(4) . . ?
C12 C13 H13A 119.3 . . ?
C9 C13 H13A 119.3 . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 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
Ho1 O8 N2 O10 179.4(4) . . . . ?
Ho1 O8 N2 O7 -1.1(4) . . . . ?
Ho1 O7 N2 O10 -179.4(4) . . . . ?
Ho1 O7 N2 O8 1.1(4) . . . . ?
O11' O11 N3 O12 84.1(19) . . . . ?
O11' O11 N3 O13 -114.2(17) . . . . ?
O11 O11' N3 O12 -112.7(18) . . . . ?
O11 O11' N3 O13 80(2) . . . . ?
Ho1 O2 C1 O1 97.3(7) 2_443 . . . ?
Ho1 O2 C1 C2 -87.6(7) 2_443 . . . ?
Ho1 O1 C1 O2 91.9(4) . . . . ?
Ho1 O1 C1 C2 -83.1(4) . . . . ?
O2 C1 C2 C3 -13.5(5) . . . . ?
O1 C1 C2 C3 161.7(3) . . . . ?
O2 C1 C2 C7 170.0(3) . . . . ?
O1 C1 C2 C7 -14.7(5) . . . . ?
C7 C2 C3 C4 2.9(5) . . . . ?
C1 C2 C3 C4 -173.6(3) . . . . ?
C2 C3 C4 C5 -1.6(5) . . . . ?
C2 C3 C4 C8 177.1(3) . . . . ?
C3 C4 C5 C6 -0.8(5) . . . . ?
C8 C4 C5 C6 -179.5(3) . . . . ?
C4 C5 C6 C7 1.9(5) . . . . ?
C4 C5 C6 C9 -179.7(3) . . . . ?
C5 C6 C7 C2 -0.7(5) . . . . ?
C9 C6 C7 C2 -179.1(3) . . . . ?
C3 C2 C7 C6 -1.7(5) . . . . ?
C1 C2 C7 C6 174.8(3) . . . . ?
Ho1 O4 C8 O3 -15.4(9) 3_444 . . . ?
Ho1 O4 C8 C4 163.9(5) 3_444 . . . ?
Ho1 O3 C8 O4 -50.9(6) 1_545 . . . ?
Ho1 O3 C8 C4 129.8(3) 1_545 . . . ?
C5 C4 C8 O4 10.8(5) . . . . ?
C3 C4 C8 O4 -167.9(3) . . . . ?
C5 C4 C8 O3 -169.8(3) . . . . ?
C3 C4 C8 O3 11.4(5) . . . . ?
C7 C6 C9 C10 149.9(4) . . . . ?
C5 C6 C9 C10 -28.5(5) . . . . ?
C7 C6 C9 C13 -30.1(5) . . . . ?
C5 C6 C9 C13 151.5(4) . . . . ?
C13 C9 C10 C11 -0.7(7) . . . . ?
C6 C9 C10 C11 179.2(4) . . . . ?
C12 N1 C11 C10 0.4(8) . . . . ?
C9 C10 C11 N1 0.2(8) . . . . ?
C11 N1 C12 C13 -0.4(7) . . . . ?
C11 N1 C12 C14 -179.5(5) . . . . ?
N1 C12 C13 C9 -0.2(6) . . . . ?
C14 C12 C13 C9 178.8(4) . . . . ?
C10 C9 C13 C12 0.7(6) . . . . ?
C6 C9 C13 C12 -179.2(4) . . . . ?

_refine_diff_density_max         0.444
_refine_diff_density_min         -0.510
_refine_diff_density_rms         0.096

####################################################################### 
# 
# 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_4_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 1568586'
_audit_update_record             
;
2017-08-12 deposited with the CCDC.
2017-09-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H14 Eu N3 O12'
_chemical_formula_weight         568.24

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'
Eu Eu -0.1578 3.6682 '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'

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

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

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

_cell_length_a                   13.9799(16)
_cell_length_b                   9.7065(12)
_cell_length_c                   17.1738(16)
_cell_angle_alpha                90
_cell_angle_beta                 127.252(6)
_cell_angle_gamma                90
_cell_volume                     1855.0(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    9977
_cell_measurement_theta_min      2.98
_cell_measurement_theta_max      27.48

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    2.035
_exptl_crystal_F_000             1112
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    3.454
_shelx_estimated_absorpt_T_min   0.724
_shelx_estimated_absorpt_T_max   0.770
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            29316
_diffrn_reflns_av_unetI/netI     0.0194
_diffrn_reflns_av_R_equivalents  0.0303
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.980
_diffrn_reflns_theta_max         27.518
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4258
_reflns_number_gt                3733
_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       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0318P)²+1.9251P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4258
_refine_ls_number_parameters     272
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0288
_refine_ls_R_factor_gt           0.0228
_refine_ls_wR_factor_ref         0.0591
_refine_ls_wR_factor_gt          0.0565
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_restrained_S_all      1.136
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Eu1 Eu -0.50926(2) -0.04278(2) -0.64947(2) 0.01600(6) Uani 1 1 d . . . . .
O1 O -0.4034(2) -0.2280(2) -0.64281(15) 0.0280(5) Uani 1 1 d . . . . .
O2 O -0.4676(3) -0.4195(3) -0.73003(17) 0.0436(7) Uani 1 1 d . . . . .
O3 O -0.5083(2) -0.8386(2) -0.58482(16) 0.0329(5) Uani 1 1 d . . . . .
O4 O -0.4521(2) -0.8237(2) -0.43298(17) 0.0331(5) Uani 1 1 d . . . . .
O6 O -0.6473(2) -0.1916(3) -0.78453(17) 0.0427(6) Uani 1 1 d . . . . .
H6A H -0.7178 -0.1637 -0.8121 0.064 Uiso 1 1 d R U . . .
H6B H -0.6338 -0.2500 -0.8014 0.064 Uiso 1 1 d R U . . .
O7 O -0.3125(3) 0.0515(3) -0.5882(2) 0.0478(7) Uani 1 1 d . . . . .
O8 O -0.3204(2) -0.0396(2) -0.47820(19) 0.0388(6) Uani 1 1 d . . . . .
O9 O -0.7103(2) 0.0175(3) -0.7131(2) 0.0472(7) Uani 1 1 d . . . . .
H9A H -0.7527 -0.0540 -0.7322 0.071 Uiso 1 1 d R U . . .
H9B H -0.7075 0.0549 -0.6676 0.071 Uiso 1 1 d R U . . .
O10 O -0.1533(3) 0.0505(5) -0.4358(3) 0.1013(16) Uani 1 1 d . . . . .
O11 O -0.0462(3) -0.2576(5) -0.4216(3) 0.0884(12) Uani 1 1 d . U . . .
O12 O 0.1169(3) -0.3139(4) -0.2826(2) 0.0746(11) Uani 1 1 d . . . . .
O13 O 0.1043(3) -0.3244(4) -0.4142(2) 0.0723(11) Uani 1 1 d . . . . .
N1 N -0.0648(3) -0.2656(4) -0.1085(2) 0.0460(8) Uani 1 1 d . . . . .
H1 H -0.0184 -0.2290 -0.0496 0.055 Uiso 1 1 d R U . . .
N2 N -0.2582(3) 0.0221(3) -0.4983(3) 0.0458(8) Uani 1 1 d . . . . .
N3 N 0.0583(3) -0.2969(5) -0.3718(3) 0.0573(10) Uani 1 1 d . . . . .
C1 C -0.4185(3) -0.3559(3) -0.6507(2) 0.0243(6) Uani 1 1 d . . . . .
C2 C -0.3827(3) -0.4376(3) -0.5623(2) 0.0234(6) Uani 1 1 d . . . . .
C3 C -0.4286(3) -0.5697(3) -0.5733(2) 0.0234(6) Uani 1 1 d . . . . .
H3A H -0.4745 -0.6115 -0.6345 0.028 Uiso 1 1 calc R U . . .
C4 C -0.4054(3) -0.6384(3) -0.4926(2) 0.0218(6) Uani 1 1 d . . . . .
C5 C -0.3347(3) -0.5775(3) -0.4009(2) 0.0244(6) Uani 1 1 d . . . . .
H5B H -0.3203 -0.6239 -0.3473 0.029 Uiso 1 1 calc R U . . .
C6 C -0.2850(3) -0.4469(3) -0.3882(2) 0.0233(6) Uani 1 1 d . . . . .
C7 C -0.3103(3) -0.3779(3) -0.4699(2) 0.0243(6) Uani 1 1 d . . . . .
H7A H -0.2784 -0.2906 -0.4625 0.029 Uiso 1 1 calc R U . . .
C8 C -0.4592(3) -0.7779(3) -0.5043(2) 0.0233(6) Uani 1 1 d . . . . .
C9 C -0.2083(3) -0.3834(3) -0.2897(2) 0.0265(6) Uani 1 1 d . . . . .
C10 C -0.2246(4) -0.4144(5) -0.2198(3) 0.0457(10) Uani 1 1 d . . . . .
H10A H -0.2844 -0.4757 -0.2340 0.055 Uiso 1 1 calc R U . . .
C11 C -0.1512(4) -0.3532(5) -0.1283(3) 0.0571(12) Uani 1 1 d . . . . .
H11A H -0.1618 -0.3728 -0.0810 0.069 Uiso 1 1 calc R U . . .
C12 C -0.0454(3) -0.2312(4) -0.1734(3) 0.0359(8) Uani 1 1 d . . . . .
C13 C -0.1181(3) -0.2904(3) -0.2657(2) 0.0308(7) Uani 1 1 d . . . . .
H13A H -0.1065 -0.2678 -0.3121 0.037 Uiso 1 1 calc R U . . .
C14 C 0.0530(4) -0.1342(5) -0.1423(3) 0.0568(11) Uani 1 1 d . . . . .
H14A H 0.0822 -0.0946 -0.0804 0.085 Uiso 1 1 calc R U . . .
H14B H 0.0238 -0.0624 -0.1902 0.085 Uiso 1 1 calc R U . . .
H14C H 0.1172 -0.1826 -0.1363 0.085 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 O4 2.214(2) 3_444 ?
Eu1 O2 2.238(2) 2_453 ?
Eu1 O3 2.268(2) 1_565 ?
Eu1 O1 2.287(2) . ?
Eu1 O9 2.391(3) . ?
Eu1 O6 2.402(2) . ?
Eu1 O7 2.451(3) . ?
Eu1 O8 2.494(3) . ?
Eu1 N2 2.902(3) . ?
Eu1 H6A 2.7968 . ?
Eu1 H9A 2.7858 . ?
Eu1 H9B 2.7627 . ?
O1 C1 1.253(4) . ?
O2 C1 1.256(4) . ?
O2 Eu1 2.238(2) 2_443 ?
O3 C8 1.257(4) . ?
O3 Eu1 2.268(2) 1_545 ?
O4 C8 1.250(4) . ?
O4 Eu1 2.214(2) 3_444 ?
O6 H6A 0.8399 . ?
O6 H6B 0.7115 . ?
O7 N2 1.274(5) . ?
O8 N2 1.264(4) . ?
O9 H9A 0.8399 . ?
O9 H9B 0.8405 . ?
O10 N2 1.214(5) . ?
O11 N3 1.224(5) . ?
O12 N3 1.235(4) . ?
O13 N3 1.258(5) . ?
N1 C12 1.340(5) . ?
N1 C11 1.342(5) . ?
N1 H1 0.8801 . ?
C1 C2 1.505(4) . ?
C2 C7 1.391(4) . ?
C2 C3 1.394(4) . ?
C3 C4 1.388(4) . ?
C3 H3A 0.9300 . ?
C4 C5 1.388(4) . ?
C4 C8 1.502(4) . ?
C5 C6 1.398(4) . ?
C5 H5B 0.9300 . ?
C6 C7 1.393(4) . ?
C6 C9 1.482(4) . ?
C7 H7A 0.9300 . ?
C9 C10 1.384(5) . ?
C9 C13 1.396(4) . ?
C10 C11 1.386(5) . ?
C10 H10A 0.9300 . ?
C11 H11A 0.9300 . ?
C12 C13 1.388(5) . ?
C12 C14 1.475(5) . ?
C13 H13A 0.9300 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 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
O4 Eu1 O2 161.74(10) 3_444 2_453 ?
O4 Eu1 O3 97.45(8) 3_444 1_565 ?
O2 Eu1 O3 86.57(8) 2_453 1_565 ?
O4 Eu1 O1 84.78(8) 3_444 . ?
O2 Eu1 O1 101.16(9) 2_453 . ?
O3 Eu1 O1 148.28(8) 1_565 . ?
O4 Eu1 O9 76.17(10) 3_444 . ?
O2 Eu1 O9 88.55(11) 2_453 . ?
O3 Eu1 O9 70.54(9) 1_565 . ?
O1 Eu1 O9 139.58(9) . . ?
O4 Eu1 O6 84.34(9) 3_444 . ?
O2 Eu1 O6 81.18(9) 2_453 . ?
O3 Eu1 O6 139.59(9) 1_565 . ?
O1 Eu1 O6 72.12(8) . . ?
O9 Eu1 O6 70.79(9) . . ?
O4 Eu1 O7 126.08(10) 3_444 . ?
O2 Eu1 O7 72.16(11) 2_453 . ?
O3 Eu1 O7 77.94(9) 1_565 . ?
O1 Eu1 O7 75.39(8) . . ?
O9 Eu1 O7 143.91(10) . . ?
O6 Eu1 O7 132.51(10) . . ?
O4 Eu1 O8 75.34(9) 3_444 . ?
O2 Eu1 O8 122.76(10) 2_453 . ?
O3 Eu1 O8 73.94(8) 1_565 . ?
O1 Eu1 O8 76.10(8) . . ?
O9 Eu1 O8 130.39(9) . . ?
O6 Eu1 O8 143.54(8) . . ?
O7 Eu1 O8 51.50(10) . . ?
O4 Eu1 N2 100.72(10) 3_444 . ?
O2 Eu1 N2 97.51(11) 2_453 . ?
O3 Eu1 N2 74.15(9) 1_565 . ?
O1 Eu1 N2 74.36(9) . . ?
O9 Eu1 N2 143.71(10) . . ?
O6 Eu1 N2 145.46(9) . . ?
O7 Eu1 N2 25.81(10) . . ?
O8 Eu1 N2 25.69(10) . . ?
O4 Eu1 H6A 83.3 3_444 . ?
O2 Eu1 H6A 79.7 2_453 . ?
O3 Eu1 H6A 123.3 1_565 . ?
O1 Eu1 H6A 88.4 . . ?
O9 Eu1 H6A 54.5 . . ?
O6 Eu1 H6A 16.4 . . ?
O7 Eu1 H6A 143.7 . . ?
O8 Eu1 H6A 154.5 . . ?
N2 Eu1 H6A 161.7 . . ?
O4 Eu1 H9A 66.9 3_444 . ?
O2 Eu1 H9A 95.8 2_453 . ?
O3 Eu1 H9A 85.8 1_565 . ?
O1 Eu1 H9A 123.3 . . ?
O9 Eu1 H9A 16.5 . . ?
O6 Eu1 H9A 57.6 . . ?
O7 Eu1 H9A 160.2 . . ?
O8 Eu1 H9A 134.1 . . ?
N2 Eu1 H9A 155.1 . . ?
H6A Eu1 H9A 42.3 . . ?
O4 Eu1 H9B 69.9 3_444 . ?
O2 Eu1 H9B 98.0 2_453 . ?
O3 Eu1 H9B 57.6 1_565 . ?
O1 Eu1 H9B 148.2 . . ?
O9 Eu1 H9B 16.9 . . ?
O6 Eu1 H9B 86.1 . . ?
O7 Eu1 H9B 135.1 . . ?
O8 Eu1 H9B 113.7 . . ?
N2 Eu1 H9B 127.9 . . ?
H6A Eu1 H9B 70.3 . . ?
H9A Eu1 H9B 28.8 . . ?
C1 O1 Eu1 135.3(2) . . ?
C1 O2 Eu1 160.8(3) . 2_443 ?
C8 O3 Eu1 141.8(2) . 1_545 ?
C8 O4 Eu1 158.4(2) . 3_444 ?
Eu1 O6 H6A 109.5 . . ?
Eu1 O6 H6B 128.0 . . ?
H6A O6 H6B 122.5 . . ?
N2 O7 Eu1 97.3(2) . . ?
N2 O8 Eu1 95.5(2) . . ?
Eu1 O9 H9A 109.5 . . ?
Eu1 O9 H9B 107.5 . . ?
H9A O9 H9B 110.2 . . ?
C12 N1 C11 123.5(3) . . ?
C12 N1 H1 118.3 . . ?
C11 N1 H1 118.2 . . ?
O10 N2 O8 122.0(4) . . ?
O10 N2 O7 122.4(4) . . ?
O8 N2 O7 115.7(3) . . ?
O10 N2 Eu1 179.2(4) . . ?
O8 N2 Eu1 58.81(18) . . ?
O7 N2 Eu1 56.88(18) . . ?
O11 N3 O12 121.6(4) . . ?
O11 N3 O13 118.3(4) . . ?
O12 N3 O13 120.1(4) . . ?
O1 C1 O2 123.3(3) . . ?
O1 C1 C2 118.9(3) . . ?
O2 C1 C2 117.7(3) . . ?
C7 C2 C3 119.7(3) . . ?
C7 C2 C1 119.9(3) . . ?
C3 C2 C1 120.2(3) . . ?
C4 C3 C2 119.7(3) . . ?
C4 C3 H3A 120.1 . . ?
C2 C3 H3A 120.1 . . ?
C5 C4 C3 120.3(3) . . ?
C5 C4 C8 119.4(3) . . ?
C3 C4 C8 120.3(3) . . ?
C4 C5 C6 120.6(3) . . ?
C4 C5 H5B 119.7 . . ?
C6 C5 H5B 119.7 . . ?
C7 C6 C5 118.7(3) . . ?
C7 C6 C9 121.2(3) . . ?
C5 C6 C9 120.1(3) . . ?
C2 C7 C6 120.9(3) . . ?
C2 C7 H7A 119.5 . . ?
C6 C7 H7A 119.5 . . ?
O4 C8 O3 125.3(3) . . ?
O4 C8 C4 117.0(3) . . ?
O3 C8 C4 117.8(3) . . ?
C10 C9 C13 118.6(3) . . ?
C10 C9 C6 121.0(3) . . ?
C13 C9 C6 120.4(3) . . ?
C9 C10 C11 119.5(3) . . ?
C9 C10 H10A 120.3 . . ?
C11 C10 H10A 120.3 . . ?
N1 C11 C10 119.7(3) . . ?
N1 C11 H11A 120.2 . . ?
C10 C11 H11A 120.2 . . ?
N1 C12 C13 118.0(3) . . ?
N1 C12 C14 118.3(3) . . ?
C13 C12 C14 123.7(3) . . ?
C12 C13 C9 120.8(3) . . ?
C12 C13 H13A 119.6 . . ?
C9 C13 H13A 119.6 . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 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
Eu1 O8 N2 O10 179.7(4) . . . . ?
Eu1 O8 N2 O7 -0.8(3) . . . . ?
Eu1 O7 N2 O10 -179.7(4) . . . . ?
Eu1 O7 N2 O8 0.9(3) . . . . ?
Eu1 O1 C1 O2 92.9(4) . . . . ?
Eu1 O1 C1 C2 -83.7(4) . . . . ?
Eu1 O2 C1 O1 96.4(7) 2_443 . . . ?
Eu1 O2 C1 C2 -87.0(7) 2_443 . . . ?
O1 C1 C2 C7 -14.2(5) . . . . ?
O2 C1 C2 C7 169.1(3) . . . . ?
O1 C1 C2 C3 161.3(3) . . . . ?
O2 C1 C2 C3 -15.4(5) . . . . ?
C7 C2 C3 C4 2.4(5) . . . . ?
C1 C2 C3 C4 -173.1(3) . . . . ?
C2 C3 C4 C5 -1.4(4) . . . . ?
C2 C3 C4 C8 177.0(3) . . . . ?
C3 C4 C5 C6 -0.6(5) . . . . ?
C8 C4 C5 C6 -179.1(3) . . . . ?
C4 C5 C6 C7 1.6(5) . . . . ?
C4 C5 C6 C9 -179.2(3) . . . . ?
C3 C2 C7 C6 -1.4(5) . . . . ?
C1 C2 C7 C6 174.1(3) . . . . ?
C5 C6 C7 C2 -0.6(5) . . . . ?
C9 C6 C7 C2 -179.7(3) . . . . ?
Eu1 O4 C8 O3 -14.3(8) 3_444 . . . ?
Eu1 O4 C8 C4 165.1(4) 3_444 . . . ?
Eu1 O3 C8 O4 -52.0(5) 1_545 . . . ?
Eu1 O3 C8 C4 128.6(3) 1_545 . . . ?
C5 C4 C8 O4 10.3(4) . . . . ?
C3 C4 C8 O4 -168.1(3) . . . . ?
C5 C4 C8 O3 -170.2(3) . . . . ?
C3 C4 C8 O3 11.3(4) . . . . ?
C7 C6 C9 C10 150.2(4) . . . . ?
C5 C6 C9 C10 -28.9(5) . . . . ?
C7 C6 C9 C13 -29.6(5) . . . . ?
C5 C6 C9 C13 151.3(3) . . . . ?
C13 C9 C10 C11 -0.3(6) . . . . ?
C6 C9 C10 C11 179.9(4) . . . . ?
C12 N1 C11 C10 0.9(7) . . . . ?
C9 C10 C11 N1 -0.5(7) . . . . ?
C11 N1 C12 C13 -0.6(6) . . . . ?
C11 N1 C12 C14 -179.6(5) . . . . ?
N1 C12 C13 C9 -0.2(5) . . . . ?
C14 C12 C13 C9 178.8(4) . . . . ?
C10 C9 C13 C12 0.7(5) . . . . ?
C6 C9 C13 C12 -179.6(3) . . . . ?

_refine_diff_density_max         0.471
_refine_diff_density_min         -0.767
_refine_diff_density_rms         0.123

####################################################################### 
# 
# 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_4_CCDC3
_database_code_depnum_ccdc_archive 'CCDC 1568590'
_audit_update_record             
;
2017-08-12 deposited with the CCDC.
2017-09-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H14 N3 O12 Sm'
_chemical_formula_weight         566.64

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

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

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

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

_cell_length_a                   13.9556(16)
_cell_length_b                   9.8837(12)
_cell_length_c                   17.3889(16)
_cell_angle_alpha                90
_cell_angle_beta                 127.918(6)
_cell_angle_gamma                90
_cell_volume                     1892.2(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    9158
_cell_measurement_theta_min      3.00
_cell_measurement_theta_max      27.51

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.989
_exptl_crystal_F_000             1108
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    3.175
_shelx_estimated_absorpt_T_min   0.742
_shelx_estimated_absorpt_T_max   0.785
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            26781
_diffrn_reflns_av_unetI/netI     0.0159
_diffrn_reflns_av_R_equivalents  0.0301
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.970
_diffrn_reflns_theta_max         25.008
_diffrn_reflns_theta_full        25.008
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3339
_reflns_number_gt                2942
_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       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0200P)²+3.2612P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3339
_refine_ls_number_parameters     272
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0259
_refine_ls_R_factor_gt           0.0200
_refine_ls_wR_factor_ref         0.0481
_refine_ls_wR_factor_gt          0.0451
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_restrained_S_all      1.151
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Sm1 Sm -0.50867(2) -0.04392(2) -0.64894(2) 0.01809(6) Uani 1 1 d . . . . .
O1 O -0.3996(2) -0.2342(2) -0.63986(15) 0.0229(5) Uani 1 1 d . . . . .
O2 O -0.4720(3) -0.4206(2) -0.72887(16) 0.0374(6) Uani 1 1 d . . . . .
O3 O -0.5072(2) -0.8341(2) -0.58541(16) 0.0295(5) Uani 1 1 d . . . . .
O4 O -0.4513(2) -0.8217(2) -0.43567(16) 0.0282(5) Uani 1 1 d . . . . .
O6 O -0.6521(2) -0.1950(3) -0.78817(17) 0.0383(6) Uani 1 1 d . . . . .
H6A H -0.7218 -0.1683 -0.8158 0.057 Uiso 1 1 d R U . . .
H6B H -0.6387 -0.2534 -0.8050 0.057 Uiso 1 1 d R U . . .
O7 O -0.3009(3) 0.0497(3) -0.5792(2) 0.0447(7) Uani 1 1 d . . . . .
O8 O -0.3151(2) -0.0409(3) -0.47389(17) 0.0342(6) Uani 1 1 d . . . . .
O9 O -0.7184(2) 0.0130(3) -0.71355(19) 0.0432(7) Uani 1 1 d . . . . .
H9A H -0.7593 -0.0562 -0.7320 0.065 Uiso 1 1 d R U . . .
H9B H -0.7156 0.0505 -0.6681 0.065 Uiso 1 1 d R U . . .
O10 O -0.1457(3) 0.0513(5) -0.4253(3) 0.1017(15) Uani 1 1 d . . . . .
O11 O -0.0549(3) -0.2550(4) -0.4262(3) 0.0781(10) Uani 1 1 d . U . . .
O12 O 0.1104(3) -0.3074(4) -0.2871(2) 0.0676(10) Uani 1 1 d . . . . .
O13 O 0.0981(3) -0.3205(4) -0.41663(19) 0.0644(10) Uani 1 1 d . . . . .
N1 N -0.0689(3) -0.2671(3) -0.1112(2) 0.0386(8) Uani 1 1 d . . . . .
H1 H -0.0246 -0.2309 -0.0542 0.046 Uiso 1 1 d R U . . .
N2 N -0.2505(3) 0.0212(3) -0.4908(3) 0.0431(8) Uani 1 1 d . . . . .
N3 N 0.0513(3) -0.2926(4) -0.3758(2) 0.0506(10) Uani 1 1 d . . . . .
C1 C -0.4183(3) -0.3590(3) -0.6487(2) 0.0202(6) Uani 1 1 d . . . . .
C2 C -0.3824(3) -0.4392(3) -0.5613(2) 0.0169(6) Uani 1 1 d . . . . .
C3 C -0.4277(3) -0.5692(3) -0.5726(2) 0.0187(6) Uani 1 1 d . . . . .
H3A H -0.4735 -0.6103 -0.6336 0.022 Uiso 1 1 calc R U . . .
C4 C -0.4047(3) -0.6377(3) -0.4931(2) 0.0163(6) Uani 1 1 d . . . . .
C5 C -0.3342(3) -0.5771(3) -0.4018(2) 0.0198(6) Uani 1 1 d . . . . .
H5B H -0.3194 -0.6229 -0.3487 0.024 Uiso 1 1 calc R U . . .
C6 C -0.2851(3) -0.4484(3) -0.3886(2) 0.0187(6) Uani 1 1 d . . . . .
C7 C -0.3106(3) -0.3801(3) -0.4692(2) 0.0184(6) Uani 1 1 d . . . . .
H7A H -0.2793 -0.2938 -0.4615 0.022 Uiso 1 1 calc R U . . .
C8 C -0.4580(3) -0.7749(3) -0.5056(2) 0.0180(6) Uani 1 1 d . . . . .
C9 C -0.2093(3) -0.3848(3) -0.2907(2) 0.0217(7) Uani 1 1 d . . . . .
C10 C -0.2260(4) -0.4159(4) -0.2217(2) 0.0391(9) Uani 1 1 d . . . . .
H10A H -0.2855 -0.4774 -0.2364 0.047 Uiso 1 1 calc R U . . .
C11 C -0.1544(4) -0.3553(5) -0.1320(3) 0.0501(12) Uani 1 1 d . . . . .
H11A H -0.1652 -0.3755 -0.0856 0.060 Uiso 1 1 calc R U . . .
C12 C -0.0485(3) -0.2321(4) -0.1744(2) 0.0310(8) Uani 1 1 d . . . . .
C13 C -0.1198(3) -0.2915(3) -0.2655(2) 0.0265(7) Uani 1 1 d . . . . .
H13A H -0.1077 -0.2685 -0.3108 0.032 Uiso 1 1 calc R U . . .
C14 C 0.0494(4) -0.1332(5) -0.1424(3) 0.0520(11) Uani 1 1 d . . . . .
H14A H 0.0848 -0.1034 -0.0774 0.078 Uiso 1 1 calc R U . . .
H14B H 0.0161 -0.0569 -0.1857 0.078 Uiso 1 1 calc R U . . .
H14C H 0.1107 -0.1752 -0.1433 0.078 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Sm1 O4 2.292(2) 3_444 ?
Sm1 O2 2.317(2) 2_453 ?
Sm1 O3 2.344(2) 1_565 ?
Sm1 O1 2.363(2) . ?
Sm1 O9 2.470(3) . ?
Sm1 O6 2.478(2) . ?
Sm1 O7 2.533(3) . ?
Sm1 O8 2.541(2) . ?
Sm1 N2 2.963(3) . ?
O1 C1 1.250(4) . ?
O2 C1 1.261(4) . ?
O2 Sm1 2.317(2) 2_443 ?
O3 C8 1.252(4) . ?
O3 Sm1 2.344(2) 1_545 ?
O4 C8 1.249(4) . ?
O4 Sm1 2.292(2) 3_444 ?
O6 H6A 0.8199 . ?
O6 H6B 0.7223 . ?
O7 N2 1.269(4) . ?
O8 N2 1.265(4) . ?
O9 H9A 0.8200 . ?
O9 H9B 0.8519 . ?
O10 N2 1.215(5) . ?
O11 N3 1.227(5) . ?
O12 N3 1.232(4) . ?
O13 N3 1.255(4) . ?
N1 C11 1.335(5) . ?
N1 C12 1.340(4) . ?
N1 H1 0.8599 . ?
C1 C2 1.502(4) . ?
C2 C3 1.391(4) . ?
C2 C7 1.392(4) . ?
C3 C4 1.388(4) . ?
C3 H3A 0.9300 . ?
C4 C5 1.389(4) . ?
C4 C8 1.497(4) . ?
C5 C6 1.395(4) . ?
C5 H5B 0.9300 . ?
C6 C7 1.390(4) . ?
C6 C9 1.483(4) . ?
C7 H7A 0.9300 . ?
C9 C13 1.389(5) . ?
C9 C10 1.390(5) . ?
C10 C11 1.369(5) . ?
C10 H10A 0.9300 . ?
C11 H11A 0.9300 . ?
C12 C13 1.380(5) . ?
C12 C14 1.482(5) . ?
C13 H13A 0.9300 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 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
O4 Sm1 O2 163.08(9) 3_444 2_453 ?
O4 Sm1 O3 98.34(8) 3_444 1_565 ?
O2 Sm1 O3 85.93(8) 2_453 1_565 ?
O4 Sm1 O1 84.09(8) 3_444 . ?
O2 Sm1 O1 100.81(8) 2_453 . ?
O3 Sm1 O1 148.67(8) 1_565 . ?
O4 Sm1 O9 74.69(9) 3_444 . ?
O2 Sm1 O9 91.43(10) 2_453 . ?
O3 Sm1 O9 71.17(9) 1_565 . ?
O1 Sm1 O9 138.26(8) . . ?
O4 Sm1 O6 84.75(8) 3_444 . ?
O2 Sm1 O6 81.51(9) 2_453 . ?
O3 Sm1 O6 139.57(8) 1_565 . ?
O1 Sm1 O6 71.71(8) . . ?
O9 Sm1 O6 70.91(8) . . ?
O4 Sm1 O7 124.30(9) 3_444 . ?
O2 Sm1 O7 72.60(10) 2_453 . ?
O3 Sm1 O7 77.02(9) 1_565 . ?
O1 Sm1 O7 76.00(8) . . ?
O9 Sm1 O7 145.31(9) . . ?
O6 Sm1 O7 133.47(9) . . ?
O4 Sm1 O8 74.75(8) 3_444 . ?
O2 Sm1 O8 122.10(9) 2_453 . ?
O3 Sm1 O8 74.34(8) 1_565 . ?
O1 Sm1 O8 76.27(8) . . ?
O9 Sm1 O8 129.20(8) . . ?
O6 Sm1 O8 143.45(8) . . ?
O7 Sm1 O8 50.25(9) . . ?
O4 Sm1 N2 99.61(10) 3_444 . ?
O2 Sm1 N2 97.30(10) 2_453 . ?
O3 Sm1 N2 73.57(9) 1_565 . ?
O1 Sm1 N2 75.23(8) . . ?
O9 Sm1 N2 142.89(9) . . ?
O6 Sm1 N2 146.02(9) . . ?
O7 Sm1 N2 25.16(9) . . ?
O8 Sm1 N2 25.10(9) . . ?
C1 O1 Sm1 134.4(2) . . ?
C1 O2 Sm1 157.3(2) . 2_443 ?
C8 O3 Sm1 140.8(2) . 1_545 ?
C8 O4 Sm1 159.6(2) . 3_444 ?
Sm1 O6 H6A 109.5 . . ?
Sm1 O6 H6B 128.4 . . ?
H6A O6 H6B 122.1 . . ?
N2 O7 Sm1 96.7(2) . . ?
N2 O8 Sm1 96.4(2) . . ?
Sm1 O9 H9A 109.5 . . ?
Sm1 O9 H9B 108.2 . . ?
H9A O9 H9B 110.5 . . ?
C11 N1 C12 123.5(3) . . ?
C11 N1 H1 118.3 . . ?
C12 N1 H1 118.3 . . ?
O10 N2 O8 121.4(4) . . ?
O10 N2 O7 122.1(4) . . ?
O8 N2 O7 116.5(3) . . ?
O10 N2 Sm1 178.1(3) . . ?
O8 N2 Sm1 58.46(17) . . ?
O7 N2 Sm1 58.10(17) . . ?
O11 N3 O12 121.0(4) . . ?
O11 N3 O13 118.8(3) . . ?
O12 N3 O13 120.1(3) . . ?
O1 C1 O2 123.3(3) . . ?
O1 C1 C2 118.8(3) . . ?
O2 C1 C2 117.8(3) . . ?
C3 C2 C7 119.6(3) . . ?
C3 C2 C1 120.3(3) . . ?
C7 C2 C1 120.0(3) . . ?
C4 C3 C2 120.1(3) . . ?
C4 C3 H3A 119.9 . . ?
C2 C3 H3A 119.9 . . ?
C3 C4 C5 119.7(3) . . ?
C3 C4 C8 120.5(3) . . ?
C5 C4 C8 119.8(3) . . ?
C4 C5 C6 120.9(3) . . ?
C4 C5 H5B 119.6 . . ?
C6 C5 H5B 119.6 . . ?
C7 C6 C5 118.8(3) . . ?
C7 C6 C9 120.7(3) . . ?
C5 C6 C9 120.5(3) . . ?
C6 C7 C2 120.9(3) . . ?
C6 C7 H7A 119.6 . . ?
C2 C7 H7A 119.6 . . ?
O4 C8 O3 124.6(3) . . ?
O4 C8 C4 117.4(3) . . ?
O3 C8 C4 118.0(3) . . ?
C13 C9 C10 118.0(3) . . ?
C13 C9 C6 120.9(3) . . ?
C10 C9 C6 121.1(3) . . ?
C11 C10 C9 119.6(3) . . ?
C11 C10 H10A 120.2 . . ?
C9 C10 H10A 120.2 . . ?
N1 C11 C10 120.0(3) . . ?
N1 C11 H11A 120.0 . . ?
C10 C11 H11A 120.0 . . ?
N1 C12 C13 117.7(3) . . ?
N1 C12 C14 118.3(3) . . ?
C13 C12 C14 124.0(3) . . ?
C12 C13 C9 121.2(3) . . ?
C12 C13 H13A 119.4 . . ?
C9 C13 H13A 119.4 . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 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
Sm1 O8 N2 O10 177.8(4) . . . . ?
Sm1 O8 N2 O7 -2.3(3) . . . . ?
Sm1 O7 N2 O10 -177.8(4) . . . . ?
Sm1 O7 N2 O8 2.4(3) . . . . ?
Sm1 O1 C1 O2 90.5(4) . . . . ?
Sm1 O1 C1 C2 -85.5(3) . . . . ?
Sm1 O2 C1 O1 94.1(6) 2_443 . . . ?
Sm1 O2 C1 C2 -89.8(6) 2_443 . . . ?
O1 C1 C2 C3 164.1(3) . . . . ?
O2 C1 C2 C3 -12.2(4) . . . . ?
O1 C1 C2 C7 -11.3(4) . . . . ?
O2 C1 C2 C7 172.4(3) . . . . ?
C7 C2 C3 C4 2.1(4) . . . . ?
C1 C2 C3 C4 -173.3(3) . . . . ?
C2 C3 C4 C5 -1.3(4) . . . . ?
C2 C3 C4 C8 177.1(3) . . . . ?
C3 C4 C5 C6 -0.5(4) . . . . ?
C8 C4 C5 C6 -178.9(3) . . . . ?
C4 C5 C6 C7 1.6(4) . . . . ?
C4 C5 C6 C9 -179.6(3) . . . . ?
C5 C6 C7 C2 -0.8(4) . . . . ?
C9 C6 C7 C2 -179.6(3) . . . . ?
C3 C2 C7 C6 -1.1(4) . . . . ?
C1 C2 C7 C6 174.4(3) . . . . ?
Sm1 O4 C8 O3 -16.4(8) 3_444 . . . ?
Sm1 O4 C8 C4 162.8(5) 3_444 . . . ?
Sm1 O3 C8 O4 -49.8(5) 1_545 . . . ?
Sm1 O3 C8 C4 131.0(3) 1_545 . . . ?
C3 C4 C8 O4 -168.4(3) . . . . ?
C5 C4 C8 O4 10.1(4) . . . . ?
C3 C4 C8 O3 10.9(4) . . . . ?
C5 C4 C8 O3 -170.7(3) . . . . ?
C7 C6 C9 C13 -29.4(5) . . . . ?
C5 C6 C9 C13 151.8(3) . . . . ?
C7 C6 C9 C10 150.2(3) . . . . ?
C5 C6 C9 C10 -28.6(5) . . . . ?
C13 C9 C10 C11 -0.4(6) . . . . ?
C6 C9 C10 C11 180.0(4) . . . . ?
C12 N1 C11 C10 0.5(7) . . . . ?
C9 C10 C11 N1 -0.1(7) . . . . ?
C11 N1 C12 C13 -0.3(6) . . . . ?
C11 N1 C12 C14 -179.9(4) . . . . ?
N1 C12 C13 C9 -0.3(5) . . . . ?
C14 C12 C13 C9 179.3(4) . . . . ?
C10 C9 C13 C12 0.7(5) . . . . ?
C6 C9 C13 C12 -179.8(3) . . . . ?

_refine_diff_density_max         0.932
_refine_diff_density_min         -0.868
_refine_diff_density_rms         0.086

####################################################################### 
# 
# 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_4_CCDC4
_database_code_depnum_ccdc_archive 'CCDC 1568589'
_audit_update_record             
;
2017-08-12 deposited with the CCDC.
2017-09-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H14 N3 Nd O12'
_chemical_formula_weight         560.52

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'
Nd Nd -0.1943 3.0179 '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'

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

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

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

_cell_length_a                   13.9481(16)
_cell_length_b                   9.9518(12)
_cell_length_c                   17.4760(16)
_cell_angle_alpha                90
_cell_angle_beta                 128.175(6)
_cell_angle_gamma                90
_cell_volume                     1907.0(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    9944
_cell_measurement_theta_min      3.10
_cell_measurement_theta_max      27.50

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.952
_exptl_crystal_F_000             1100
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    2.794
_shelx_estimated_absorpt_T_min   0.768
_shelx_estimated_absorpt_T_max   0.807
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            30108
_diffrn_reflns_av_unetI/netI     0.0266
_diffrn_reflns_av_R_equivalents  0.0557
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.965
_diffrn_reflns_theta_max         25.010
_diffrn_reflns_theta_full        25.010
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3356
_reflns_number_gt                2812
_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       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0211P)²+0.9289P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3356
_refine_ls_number_parameters     281
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0321
_refine_ls_R_factor_gt           0.0211
_refine_ls_wR_factor_ref         0.0454
_refine_ls_wR_factor_gt          0.0426
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.031
_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
Nd1 Nd -0.50885(2) -0.04431(2) -0.64893(2) 0.01804(6) Uani 1 1 d . . . . .
O1 O -0.39869(19) -0.2362(2) -0.63900(14) 0.0217(5) Uani 1 1 d . . . . .
O2 O -0.4737(2) -0.4213(2) -0.72829(15) 0.0361(6) Uani 1 1 d . . . . .
O3 O -0.5073(2) -0.8324(2) -0.58607(15) 0.0290(5) Uani 1 1 d . . . . .
O4 O -0.4509(2) -0.8207(2) -0.43668(16) 0.0284(5) Uani 1 1 d . . . . .
O6 O -0.6544(2) -0.1964(2) -0.79016(16) 0.0392(6) Uani 1 1 d . . . . .
H6A H -0.7262 -0.1693 -0.8187 0.059 Uiso 1 1 d R U . . .
H6B H -0.6409 -0.2548 -0.8070 0.059 Uiso 1 1 d R U . . .
O7 O -0.2970(2) 0.0485(3) -0.5760(2) 0.0453(7) Uani 1 1 d . . . . .
O8 O -0.3132(2) -0.0416(2) -0.47212(16) 0.0348(6) Uani 1 1 d . . . . .
O9 O -0.7220(2) 0.0108(3) -0.71377(18) 0.0420(7) Uani 1 1 d . . . . .
H9A H -0.7636 -0.0600 -0.7326 0.063 Uiso 1 1 d R U . . .
H9B H -0.7192 0.0483 -0.6683 0.063 Uiso 1 1 d R U . . .
O10 O -0.1433(3) 0.0522(4) -0.4216(3) 0.1022(14) Uani 1 1 d . . . . .
O11 O -0.0582(14) -0.276(2) -0.4299(17) 0.068(5) Uani 0.5 1 d . . P . .
O11' O -0.058(2) -0.228(2) -0.4262(18) 0.086(7) Uani 0.5 1 d . . P . .
O12 O 0.1078(3) -0.3048(4) -0.2886(2) 0.0685(10) Uani 1 1 d . . . . .
O13 O 0.0955(3) -0.3181(4) -0.41787(19) 0.0651(10) Uani 1 1 d . . . . .
N1 N -0.0703(3) -0.2680(3) -0.1121(2) 0.0388(8) Uani 1 1 d . . . . .
H1 H -0.0255 -0.2305 -0.0541 0.047 Uiso 1 1 d R U . . .
N2 N -0.2477(3) 0.0207(3) -0.4879(3) 0.0442(8) Uani 1 1 d . . . . .
N3 N 0.0472(3) -0.2904(4) -0.3782(2) 0.0519(9) Uani 1 1 d . . . . .
C1 C -0.4184(3) -0.3599(3) -0.6479(2) 0.0205(7) Uani 1 1 d . . . . .
C2 C -0.3833(3) -0.4397(3) -0.5613(2) 0.0167(6) Uani 1 1 d . . . . .
C3 C -0.4276(3) -0.5686(3) -0.5728(2) 0.0177(6) Uani 1 1 d . . . . .
H3A H -0.4728 -0.6096 -0.6336 0.021 Uiso 1 1 calc R U . . .
C4 C -0.4046(3) -0.6369(3) -0.4935(2) 0.0165(6) Uani 1 1 d . . . . .
C5 C -0.3340(3) -0.5775(3) -0.4023(2) 0.0192(7) Uani 1 1 d . . . . .
H5B H -0.3187 -0.6235 -0.3494 0.023 Uiso 1 1 calc R U . . .
C6 C -0.2854(3) -0.4490(3) -0.3890(2) 0.0181(6) Uani 1 1 d . . . . .
C7 C -0.3111(3) -0.3809(3) -0.4691(2) 0.0189(6) Uani 1 1 d . . . . .
H7A H -0.2798 -0.2951 -0.4613 0.023 Uiso 1 1 calc R U . . .
C8 C -0.4578(3) -0.7734(3) -0.5063(2) 0.0187(7) Uani 1 1 d . . . . .
C9 C -0.2100(3) -0.3858(3) -0.2913(2) 0.0213(7) Uani 1 1 d . . . . .
C10 C -0.2263(3) -0.4166(4) -0.2226(2) 0.0392(10) Uani 1 1 d . . . . .
H10A H -0.2858 -0.4781 -0.2375 0.047 Uiso 1 1 calc R U . . .
C11 C -0.1548(4) -0.3566(5) -0.1330(3) 0.0486(11) Uani 1 1 d . . . . .
H11A H -0.1653 -0.3778 -0.0868 0.058 Uiso 1 1 calc R U . . .
C12 C -0.0499(3) -0.2331(4) -0.1748(2) 0.0307(8) Uani 1 1 d . . . . .
C13 C -0.1204(3) -0.2920(3) -0.2657(2) 0.0256(7) Uani 1 1 d . . . . .
H13A H -0.1079 -0.2688 -0.3105 0.031 Uiso 1 1 calc R U . . .
C14 C 0.0482(4) -0.1331(4) -0.1424(3) 0.0523(11) Uani 1 1 d . . . . .
H14A H 0.0710 -0.0890 -0.0844 0.078 Uiso 1 1 calc R U . . .
H14B H 0.0189 -0.0677 -0.1928 0.078 Uiso 1 1 calc R U . . .
H14C H 0.1179 -0.1783 -0.1291 0.078 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Nd1 O4 2.323(2) 3_444 ?
Nd1 O2 2.349(2) 2_453 ?
Nd1 O3 2.372(2) 1_565 ?
Nd1 O1 2.389(2) . ?
Nd1 O9 2.502(2) . ?
Nd1 O6 2.512(2) . ?
Nd1 O7 2.560(3) . ?
Nd1 O8 2.563(2) . ?
Nd1 N2 2.989(3) . ?
O1 C1 1.250(4) . ?
O2 C1 1.265(3) . ?
O2 Nd1 2.349(2) 2_443 ?
O3 C8 1.254(4) . ?
O3 Nd1 2.372(2) 1_545 ?
O4 C8 1.251(4) . ?
O4 Nd1 2.323(2) 3_444 ?
O6 H6A 0.8400 . ?
O6 H6B 0.7265 . ?
O7 N2 1.269(4) . ?
O8 N2 1.267(4) . ?
O9 H9A 0.8399 . ?
O9 H9B 0.8565 . ?
O10 N2 1.214(4) . ?
O11 N3 1.166(16) . ?
O11' N3 1.31(2) . ?
O12 N3 1.246(4) . ?
O13 N3 1.259(4) . ?
N1 C11 1.330(5) . ?
N1 C12 1.337(4) . ?
N1 H1 0.8800 . ?
C1 C2 1.498(4) . ?
C2 C3 1.383(4) . ?
C2 C7 1.396(4) . ?
C3 C4 1.392(4) . ?
C3 H3A 0.9300 . ?
C4 C5 1.385(4) . ?
C4 C8 1.497(4) . ?
C5 C6 1.398(4) . ?
C5 H5B 0.9300 . ?
C6 C7 1.388(4) . ?
C6 C9 1.482(4) . ?
C7 H7A 0.9300 . ?
C9 C10 1.387(4) . ?
C9 C13 1.394(4) . ?
C10 C11 1.369(5) . ?
C10 H10A 0.9300 . ?
C11 H11A 0.9300 . ?
C12 C13 1.379(4) . ?
C12 C14 1.492(5) . ?
C13 H13A 0.9300 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 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
O4 Nd1 O2 163.72(9) 3_444 2_453 ?
O4 Nd1 O3 98.78(7) 3_444 1_565 ?
O2 Nd1 O3 85.73(7) 2_453 1_565 ?
O4 Nd1 O1 83.78(7) 3_444 . ?
O2 Nd1 O1 100.49(8) 2_453 . ?
O3 Nd1 O1 148.83(8) 1_565 . ?
O4 Nd1 O9 74.10(8) 3_444 . ?
O2 Nd1 O9 92.77(9) 2_453 . ?
O3 Nd1 O9 71.51(8) 1_565 . ?
O1 Nd1 O9 137.66(8) . . ?
O4 Nd1 O6 85.06(8) 3_444 . ?
O2 Nd1 O6 81.50(8) 2_453 . ?
O3 Nd1 O6 139.58(8) 1_565 . ?
O1 Nd1 O6 71.50(7) . . ?
O9 Nd1 O6 71.01(8) . . ?
O4 Nd1 O7 123.51(8) 3_444 . ?
O2 Nd1 O7 72.72(9) 2_453 . ?
O3 Nd1 O7 76.78(8) 1_565 . ?
O1 Nd1 O7 76.07(8) . . ?
O9 Nd1 O7 146.02(8) . . ?
O6 Nd1 O7 133.61(8) . . ?
O4 Nd1 O8 74.39(8) 3_444 . ?
O2 Nd1 O8 121.85(9) 2_453 . ?
O3 Nd1 O8 74.58(8) 1_565 . ?
O1 Nd1 O8 76.31(7) . . ?
O9 Nd1 O8 128.70(8) . . ?
O6 Nd1 O8 143.37(8) . . ?
O7 Nd1 O8 49.82(8) . . ?
O4 Nd1 N2 99.08(9) 3_444 . ?
O2 Nd1 N2 97.20(10) 2_453 . ?
O3 Nd1 N2 73.40(8) 1_565 . ?
O1 Nd1 N2 75.52(8) . . ?
O9 Nd1 N2 142.59(9) . . ?
O6 Nd1 N2 146.11(8) . . ?
O7 Nd1 N2 24.94(9) . . ?
O8 Nd1 N2 24.90(8) . . ?
C1 O1 Nd1 134.1(2) . . ?
C1 O2 Nd1 156.0(2) . 2_443 ?
C8 O3 Nd1 140.50(19) . 1_545 ?
C8 O4 Nd1 159.9(2) . 3_444 ?
Nd1 O6 H6A 109.5 . . ?
Nd1 O6 H6B 128.7 . . ?
H6A O6 H6B 121.8 . . ?
N2 O7 Nd1 96.8(2) . . ?
N2 O8 Nd1 96.7(2) . . ?
Nd1 O9 H9A 109.5 . . ?
Nd1 O9 H9B 108.4 . . ?
H9A O9 H9B 110.6 . . ?
C11 N1 C12 123.2(3) . . ?
C11 N1 H1 118.4 . . ?
C12 N1 H1 118.4 . . ?
O10 N2 O8 121.3(4) . . ?
O10 N2 O7 122.1(4) . . ?
O8 N2 O7 116.6(3) . . ?
O10 N2 Nd1 177.1(3) . . ?
O8 N2 Nd1 58.41(16) . . ?
O7 N2 Nd1 58.27(17) . . ?
O11 N3 O12 122.6(12) . . ?
O11 N3 O13 116.6(13) . . ?
O12 N3 O13 119.3(3) . . ?
O11 N3 O11' 21(2) . . ?
O12 N3 O11' 118.7(12) . . ?
O13 N3 O11' 121.2(12) . . ?
O1 C1 O2 123.4(3) . . ?
O1 C1 C2 119.1(3) . . ?
O2 C1 C2 117.4(3) . . ?
C3 C2 C7 119.7(3) . . ?
C3 C2 C1 120.5(3) . . ?
C7 C2 C1 119.7(3) . . ?
C2 C3 C4 120.1(3) . . ?
C2 C3 H3A 120.0 . . ?
C4 C3 H3A 120.0 . . ?
C5 C4 C3 120.0(3) . . ?
C5 C4 C8 119.6(3) . . ?
C3 C4 C8 120.4(3) . . ?
C4 C5 C6 120.6(3) . . ?
C4 C5 H5B 119.7 . . ?
C6 C5 H5B 119.7 . . ?
C7 C6 C5 118.8(3) . . ?
C7 C6 C9 120.8(3) . . ?
C5 C6 C9 120.3(3) . . ?
C6 C7 C2 120.8(3) . . ?
C6 C7 H7A 119.6 . . ?
C2 C7 H7A 119.6 . . ?
O4 C8 O3 124.3(3) . . ?
O4 C8 C4 117.5(3) . . ?
O3 C8 C4 118.2(3) . . ?
C10 C9 C13 117.7(3) . . ?
C10 C9 C6 121.6(3) . . ?
C13 C9 C6 120.7(3) . . ?
C11 C10 C9 120.0(3) . . ?
C11 C10 H10A 120.0 . . ?
C9 C10 H10A 120.0 . . ?
N1 C11 C10 119.9(3) . . ?
N1 C11 H11A 120.0 . . ?
C10 C11 H11A 120.0 . . ?
N1 C12 C13 118.2(3) . . ?
N1 C12 C14 118.1(3) . . ?
C13 C12 C14 123.6(3) . . ?
C12 C13 C9 120.9(3) . . ?
C12 C13 H13A 119.5 . . ?
C9 C13 H13A 119.5 . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 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
Nd1 O8 N2 O10 176.6(4) . . . . ?
Nd1 O8 N2 O7 -3.2(3) . . . . ?
Nd1 O7 N2 O10 -176.6(4) . . . . ?
Nd1 O7 N2 O8 3.2(3) . . . . ?
Nd1 O1 C1 O2 89.9(4) . . . . ?
Nd1 O1 C1 C2 -85.6(3) . . . . ?
Nd1 O2 C1 O1 92.7(5) 2_443 . . . ?
Nd1 O2 C1 C2 -91.7(5) 2_443 . . . ?
O1 C1 C2 C3 165.3(3) . . . . ?
O2 C1 C2 C3 -10.5(4) . . . . ?
O1 C1 C2 C7 -11.0(4) . . . . ?
O2 C1 C2 C7 173.3(3) . . . . ?
C7 C2 C3 C4 2.7(4) . . . . ?
C1 C2 C3 C4 -173.5(3) . . . . ?
C2 C3 C4 C5 -2.1(4) . . . . ?
C2 C3 C4 C8 176.7(3) . . . . ?
C3 C4 C5 C6 0.1(4) . . . . ?
C8 C4 C5 C6 -178.7(3) . . . . ?
C4 C5 C6 C7 1.2(4) . . . . ?
C4 C5 C6 C9 179.9(3) . . . . ?
C5 C6 C7 C2 -0.5(4) . . . . ?
C9 C6 C7 C2 -179.2(3) . . . . ?
C3 C2 C7 C6 -1.4(4) . . . . ?
C1 C2 C7 C6 174.8(3) . . . . ?
Nd1 O4 C8 O3 -17.4(8) 3_444 . . . ?
Nd1 O4 C8 C4 161.9(5) 3_444 . . . ?
Nd1 O3 C8 O4 -48.9(5) 1_545 . . . ?
Nd1 O3 C8 C4 131.8(3) 1_545 . . . ?
C5 C4 C8 O4 10.1(4) . . . . ?
C3 C4 C8 O4 -168.7(3) . . . . ?
C5 C4 C8 O3 -170.5(3) . . . . ?
C3 C4 C8 O3 10.6(4) . . . . ?
C7 C6 C9 C10 150.1(3) . . . . ?
C5 C6 C9 C10 -28.6(5) . . . . ?
C7 C6 C9 C13 -29.4(4) . . . . ?
C5 C6 C9 C13 151.9(3) . . . . ?
C13 C9 C10 C11 -0.7(6) . . . . ?
C6 C9 C10 C11 179.8(4) . . . . ?
C12 N1 C11 C10 -0.2(7) . . . . ?
C9 C10 C11 N1 0.5(6) . . . . ?
C11 N1 C12 C13 0.1(6) . . . . ?
C11 N1 C12 C14 -179.6(4) . . . . ?
N1 C12 C13 C9 -0.3(5) . . . . ?
C14 C12 C13 C9 179.4(4) . . . . ?
C10 C9 C13 C12 0.6(5) . . . . ?
C6 C9 C13 C12 -179.9(3) . . . . ?

_refine_diff_density_max         0.391
_refine_diff_density_min         -0.378
_refine_diff_density_rms         0.080

####################################################################### 
# 
# 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_4_CCDC5
_database_code_depnum_ccdc_archive 'CCDC 1568592'
_audit_update_record             
;
2017-08-12 deposited with the CCDC.
2017-09-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H14 N3 O12 Yb'
_chemical_formula_weight         589.32

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

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

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

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

_cell_length_a                   13.9967(16)
_cell_length_b                   9.6613(12)
_cell_length_c                   17.1032(16)
_cell_angle_alpha                90
_cell_angle_beta                 127.111(7)
_cell_angle_gamma                90
_cell_volume                     1844.4(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    9858
_cell_measurement_theta_min      3.01
_cell_measurement_theta_max      27.54

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    2.122
_exptl_crystal_F_000             1140
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    5.144
_shelx_estimated_absorpt_T_min   0.627
_shelx_estimated_absorpt_T_max   0.684
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            28606
_diffrn_reflns_av_unetI/netI     0.0112
_diffrn_reflns_av_R_equivalents  0.0221
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.788
_diffrn_reflns_theta_max         25.010
_diffrn_reflns_theta_full        25.010
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3255
_reflns_number_gt                3034
_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       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0197P)²+2.4383P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3255
_refine_ls_number_parameters     281
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0183
_refine_ls_R_factor_gt           0.0161
_refine_ls_wR_factor_ref         0.0411
_refine_ls_wR_factor_gt          0.0398
_refine_ls_goodness_of_fit_ref   1.142
_refine_ls_restrained_S_all      1.141
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Yb1 Yb -0.50962(2) -0.04244(2) -0.64966(2) 0.01708(5) Uani 1 1 d . . . . .
O1 O -0.40451(17) -0.22680(18) -0.64384(13) 0.0212(4) Uani 1 1 d . . . . .
O2 O -0.4667(2) -0.4193(2) -0.73025(15) 0.0380(6) Uani 1 1 d . . . . .
O3 O -0.50753(19) -0.84001(19) -0.58416(14) 0.0258(4) Uani 1 1 d . . . . .
O4 O -0.45227(19) -0.82484(19) -0.43256(15) 0.0259(4) Uani 1 1 d . . . . .
O6 O -0.64639(19) -0.1912(2) -0.78336(15) 0.0347(5) Uani 1 1 d . . . . .
H6A H -0.7167 -0.1631 -0.8108 0.052 Uiso 1 1 d R U . . .
H6B H -0.6329 -0.2496 -0.8002 0.052 Uiso 1 1 d R U . . .
O7 O -0.3158(2) 0.0519(2) -0.5903(2) 0.0417(6) Uani 1 1 d . . . . .
O8 O -0.3217(2) -0.0399(2) -0.47923(16) 0.0328(5) Uani 1 1 d . . . . .
O9 O -0.7082(2) 0.0187(2) -0.71298(18) 0.0409(6) Uani 1 1 d . . . . .
H9A H -0.7507 -0.0529 -0.7322 0.061 Uiso 1 1 d R U . . .
H9B H -0.7054 0.0561 -0.6675 0.061 Uiso 1 1 d R U . . .
O10 O -0.1554(3) 0.0502(4) -0.4387(3) 0.0928(13) Uani 1 1 d . . . . .
O11 O -0.0306(8) -0.2241(9) -0.4098(7) 0.067(3) Uani 0.5 1 d . U P . .
O11' O -0.0530(5) -0.2831(8) -0.4273(4) 0.0427(14) Uani 0.5 1 d . . P . .
O12 O 0.1184(3) -0.3162(4) -0.28167(19) 0.0678(9) Uani 1 1 d . . . . .
O13 O 0.1062(2) -0.3264(4) -0.41302(18) 0.0648(9) Uani 1 1 d . . . . .
N1 N -0.0637(2) -0.2663(3) -0.10785(19) 0.0396(7) Uani 1 1 d . . . . .
H1 H -0.0169 -0.2300 -0.0488 0.048 Uiso 1 1 d R U . . .
N2 N -0.2606(3) 0.0222(3) -0.5006(2) 0.0387(7) Uani 1 1 d . . . . .
N3 N 0.0599(3) -0.2984(4) -0.3707(2) 0.0504(8) Uani 1 1 d . . . . .
C1 C -0.4182(2) -0.3557(3) -0.65098(19) 0.0202(6) Uani 1 1 d . . . . .
C2 C -0.3830(2) -0.4373(3) -0.56261(19) 0.0163(5) Uani 1 1 d . . . . .
C3 C -0.4287(2) -0.5694(3) -0.57343(19) 0.0175(5) Uani 1 1 d . . . . .
H3A H -0.4745 -0.6114 -0.6348 0.021 Uiso 1 1 calc R U . . .
C4 C -0.4058(2) -0.6388(3) -0.49243(18) 0.0159(5) Uani 1 1 d . . . . .
C5 C -0.3351(2) -0.5777(3) -0.40063(19) 0.0187(5) Uani 1 1 d . . . . .
H5B H -0.3209 -0.6240 -0.3468 0.022 Uiso 1 1 calc R U . . .
C6 C -0.2850(2) -0.4467(3) -0.38818(19) 0.0177(5) Uani 1 1 d . . . . .
C7 C -0.3104(2) -0.3774(3) -0.46996(19) 0.0179(5) Uani 1 1 d . . . . .
H7A H -0.2784 -0.2898 -0.4627 0.021 Uiso 1 1 calc R U . . .
C8 C -0.4592(2) -0.7786(3) -0.50417(19) 0.0171(5) Uani 1 1 d . . . . .
C9 C -0.2081(2) -0.3831(3) -0.28930(19) 0.0207(6) Uani 1 1 d . . . . .
C10 C -0.2236(3) -0.4128(4) -0.2184(2) 0.0405(8) Uani 1 1 d . . . . .
H10A H -0.2838 -0.4733 -0.2325 0.049 Uiso 1 1 calc R U . . .
C11 C -0.1504(3) -0.3535(5) -0.1280(3) 0.0526(11) Uani 1 1 d . . . . .
H11A H -0.1607 -0.3735 -0.0803 0.063 Uiso 1 1 calc R U . . .
C12 C -0.0450(3) -0.2318(3) -0.1733(2) 0.0304(7) Uani 1 1 d . . . . .
C13 C -0.1177(3) -0.2906(3) -0.2652(2) 0.0259(6) Uani 1 1 d . . . . .
H13A H -0.1063 -0.2682 -0.3119 0.031 Uiso 1 1 calc R U . . .
C14 C 0.0535(3) -0.1339(4) -0.1424(3) 0.0514(10) Uani 1 1 d . . . . .
H14A H 0.0894 -0.1031 -0.0767 0.077 Uiso 1 1 calc R U . . .
H14B H 0.0221 -0.0557 -0.1858 0.077 Uiso 1 1 calc R U . . .
H14C H 0.1128 -0.1794 -0.1446 0.077 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Yb1 O4 2.1934(18) 3_444 ?
Yb1 O2 2.219(2) 2_453 ?
Yb1 O3 2.2452(18) 1_565 ?
Yb1 O1 2.2738(18) . ?
Yb1 O9 2.369(2) . ?
Yb1 O6 2.382(2) . ?
Yb1 O7 2.429(2) . ?
Yb1 O8 2.483(2) . ?
Yb1 N2 2.883(3) . ?
Yb1 H9B 2.7385 . ?
O1 C1 1.255(3) . ?
O2 C1 1.251(3) . ?
O2 Yb1 2.219(2) 2_443 ?
O3 C8 1.251(3) . ?
O3 Yb1 2.2453(18) 1_545 ?
O4 C8 1.251(3) . ?
O4 Yb1 2.1934(18) 3_444 ?
O6 H6A 0.8400 . ?
O6 H6B 0.7087 . ?
O7 N2 1.267(4) . ?
O8 N2 1.265(4) . ?
O9 H9A 0.8400 . ?
O9 H9B 0.8370 . ?
O10 N2 1.217(4) . ?
O11 O11' 0.632(10) . ?
O11 N3 1.243(10) . ?
O11' N3 1.270(6) . ?
O12 N3 1.231(4) . ?
O13 N3 1.257(4) . ?
N1 C12 1.338(4) . ?
N1 C11 1.340(4) . ?
N1 H1 0.8798 . ?
C1 C2 1.500(4) . ?
C2 C3 1.389(4) . ?
C2 C7 1.391(4) . ?
C3 C4 1.391(4) . ?
C3 H3A 0.9300 . ?
C4 C5 1.385(4) . ?
C4 C8 1.497(4) . ?
C5 C6 1.399(4) . ?
C5 H5B 0.9300 . ?
C6 C7 1.390(4) . ?
C6 C9 1.483(4) . ?
C7 H7A 0.9300 . ?
C9 C10 1.384(4) . ?
C9 C13 1.393(4) . ?
C10 C11 1.363(5) . ?
C10 H10A 0.9300 . ?
C11 H11A 0.9300 . ?
C12 C13 1.378(4) . ?
C12 C14 1.481(5) . ?
C13 H13A 0.9300 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 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
O4 Yb1 O2 161.57(9) 3_444 2_453 ?
O4 Yb1 O3 97.15(7) 3_444 1_565 ?
O2 Yb1 O3 86.81(7) 2_453 1_565 ?
O4 Yb1 O1 85.13(7) 3_444 . ?
O2 Yb1 O1 101.06(8) 2_453 . ?
O3 Yb1 O1 147.90(7) 1_565 . ?
O4 Yb1 O9 76.52(9) 3_444 . ?
O2 Yb1 O9 87.96(10) 2_453 . ?
O3 Yb1 O9 70.70(8) 1_565 . ?
O1 Yb1 O9 139.90(8) . . ?
O4 Yb1 O6 84.11(8) 3_444 . ?
O2 Yb1 O6 81.39(8) 2_453 . ?
O3 Yb1 O6 139.94(7) 1_565 . ?
O1 Yb1 O6 72.15(7) . . ?
O9 Yb1 O6 70.74(8) . . ?
O4 Yb1 O7 126.44(8) 3_444 . ?
O2 Yb1 O7 71.98(9) 2_453 . ?
O3 Yb1 O7 77.86(8) 1_565 . ?
O1 Yb1 O7 75.25(7) . . ?
O9 Yb1 O7 143.50(8) . . ?
O6 Yb1 O7 132.49(8) . . ?
O4 Yb1 O8 75.42(8) 3_444 . ?
O2 Yb1 O8 122.83(9) 2_453 . ?
O3 Yb1 O8 73.73(7) 1_565 . ?
O1 Yb1 O8 75.95(7) . . ?
O9 Yb1 O8 130.83(8) . . ?
O6 Yb1 O8 143.27(7) . . ?
O7 Yb1 O8 51.74(8) . . ?
O4 Yb1 N2 101.03(9) 3_444 . ?
O2 Yb1 N2 97.36(10) 2_453 . ?
O3 Yb1 N2 74.05(8) 1_565 . ?
O1 Yb1 N2 74.10(7) . . ?
O9 Yb1 N2 143.97(8) . . ?
O6 Yb1 N2 145.28(8) . . ?
O7 Yb1 N2 25.82(9) . . ?
O8 Yb1 N2 25.92(8) . . ?
O4 Yb1 H9B 70.2 3_444 . ?
O2 Yb1 H9B 97.5 2_453 . ?
O3 Yb1 H9B 57.6 1_565 . ?
O1 Yb1 H9B 148.7 . . ?
O9 Yb1 H9B 17.0 . . ?
O6 Yb1 H9B 86.1 . . ?
O7 Yb1 H9B 135.0 . . ?
O8 Yb1 H9B 114.0 . . ?
N2 Yb1 H9B 128.1 . . ?
C1 O1 Yb1 135.75(18) . . ?
C1 O2 Yb1 161.2(2) . 2_443 ?
C8 O3 Yb1 142.59(18) . 1_545 ?
C8 O4 Yb1 158.59(18) . 3_444 ?
Yb1 O6 H6A 109.5 . . ?
Yb1 O6 H6B 127.8 . . ?
H6A O6 H6B 122.7 . . ?
N2 O7 Yb1 97.55(18) . . ?
N2 O8 Yb1 95.02(18) . . ?
Yb1 O9 H9A 109.5 . . ?
Yb1 O9 H9B 107.4 . . ?
H9A O9 H9B 110.1 . . ?
O11' O11 N3 77.8(12) . . ?
O11 O11' N3 73.1(12) . . ?
C12 N1 C11 123.1(3) . . ?
C12 N1 H1 118.3 . . ?
C11 N1 H1 118.5 . . ?
O10 N2 O8 121.9(4) . . ?
O10 N2 O7 122.4(4) . . ?
O8 N2 O7 115.7(3) . . ?
O10 N2 Yb1 179.1(3) . . ?
O8 N2 Yb1 59.06(15) . . ?
O7 N2 Yb1 56.63(15) . . ?
O12 N3 O11 116.5(5) . . ?
O12 N3 O13 119.6(3) . . ?
O11 N3 O13 121.8(5) . . ?
O12 N3 O11' 123.5(4) . . ?
O11 N3 O11' 29.1(4) . . ?
O13 N3 O11' 115.1(4) . . ?
O2 C1 O1 122.9(3) . . ?
O2 C1 C2 117.9(2) . . ?
O1 C1 C2 119.1(2) . . ?
C3 C2 C7 119.7(2) . . ?
C3 C2 C1 120.3(2) . . ?
C7 C2 C1 119.9(2) . . ?
C2 C3 C4 120.0(2) . . ?
C2 C3 H3A 120.0 . . ?
C4 C3 H3A 120.0 . . ?
C5 C4 C3 120.0(2) . . ?
C5 C4 C8 119.6(2) . . ?
C3 C4 C8 120.3(2) . . ?
C4 C5 C6 120.5(2) . . ?
C4 C5 H5B 119.7 . . ?
C6 C5 H5B 119.7 . . ?
C7 C6 C5 118.8(2) . . ?
C7 C6 C9 121.2(2) . . ?
C5 C6 C9 120.0(2) . . ?
C6 C7 C2 120.9(2) . . ?
C6 C7 H7A 119.6 . . ?
C2 C7 H7A 119.6 . . ?
O3 C8 O4 124.9(2) . . ?
O3 C8 C4 118.1(2) . . ?
O4 C8 C4 116.9(2) . . ?
C10 C9 C13 117.9(3) . . ?
C10 C9 C6 121.6(3) . . ?
C13 C9 C6 120.5(2) . . ?
C11 C10 C9 120.0(3) . . ?
C11 C10 H10A 120.0 . . ?
C9 C10 H10A 120.0 . . ?
N1 C11 C10 120.0(3) . . ?
N1 C11 H11A 120.0 . . ?
C10 C11 H11A 120.0 . . ?
N1 C12 C13 117.9(3) . . ?
N1 C12 C14 118.1(3) . . ?
C13 C12 C14 124.0(3) . . ?
C12 C13 C9 121.1(3) . . ?
C12 C13 H13A 119.5 . . ?
C9 C13 H13A 119.5 . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 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
Yb1 O8 N2 O10 -179.9(3) . . . . ?
Yb1 O8 N2 O7 -0.5(3) . . . . ?
Yb1 O7 N2 O10 179.9(3) . . . . ?
Yb1 O7 N2 O8 0.6(3) . . . . ?
O11' O11 N3 O12 -111.7(12) . . . . ?
O11' O11 N3 O13 85.0(13) . . . . ?
O11 O11' N3 O12 85.0(13) . . . . ?
O11 O11' N3 O13 -110.7(13) . . . . ?
Yb1 O2 C1 O1 97.7(6) 2_443 . . . ?
Yb1 O2 C1 C2 -86.6(6) 2_443 . . . ?
Yb1 O1 C1 O2 93.3(3) . . . . ?
Yb1 O1 C1 C2 -82.3(3) . . . . ?
O2 C1 C2 C3 -15.5(4) . . . . ?
O1 C1 C2 C3 160.4(3) . . . . ?
O2 C1 C2 C7 168.6(3) . . . . ?
O1 C1 C2 C7 -15.5(4) . . . . ?
C7 C2 C3 C4 2.7(4) . . . . ?
C1 C2 C3 C4 -173.3(2) . . . . ?
C2 C3 C4 C5 -1.6(4) . . . . ?
C2 C3 C4 C8 177.3(2) . . . . ?
C3 C4 C5 C6 -0.8(4) . . . . ?
C8 C4 C5 C6 -179.6(2) . . . . ?
C4 C5 C6 C7 1.9(4) . . . . ?
C4 C5 C6 C9 -179.2(2) . . . . ?
C5 C6 C7 C2 -0.8(4) . . . . ?
C9 C6 C7 C2 -179.7(2) . . . . ?
C3 C2 C7 C6 -1.5(4) . . . . ?
C1 C2 C7 C6 174.5(2) . . . . ?
Yb1 O3 C8 O4 -51.9(4) 1_545 . . . ?
Yb1 O3 C8 C4 128.5(3) 1_545 . . . ?
Yb1 O4 C8 O3 -14.6(7) 3_444 . . . ?
Yb1 O4 C8 C4 165.0(4) 3_444 . . . ?
C5 C4 C8 O3 -169.7(2) . . . . ?
C3 C4 C8 O3 11.5(4) . . . . ?
C5 C4 C8 O4 10.7(4) . . . . ?
C3 C4 C8 O4 -168.2(2) . . . . ?
C7 C6 C9 C10 149.9(3) . . . . ?
C5 C6 C9 C10 -29.0(4) . . . . ?
C7 C6 C9 C13 -29.9(4) . . . . ?
C5 C6 C9 C13 151.2(3) . . . . ?
C13 C9 C10 C11 -0.8(5) . . . . ?
C6 C9 C10 C11 179.4(4) . . . . ?
C12 N1 C11 C10 0.8(7) . . . . ?
C9 C10 C11 N1 0.1(7) . . . . ?
C11 N1 C12 C13 -0.9(5) . . . . ?
C11 N1 C12 C14 179.8(4) . . . . ?
N1 C12 C13 C9 0.1(5) . . . . ?
C14 C12 C13 C9 179.4(3) . . . . ?
C10 C9 C13 C12 0.8(5) . . . . ?
C6 C9 C13 C12 -179.4(3) . . . . ?

_refine_diff_density_max         0.427
_refine_diff_density_min         -0.679
_refine_diff_density_rms         0.090

####################################################################### 
# 
# 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_4_CCDC6
_database_code_depnum_ccdc_archive 'CCDC 1568587'
_audit_update_record             
;
2017-08-12 deposited with the CCDC.
2017-09-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H14 Gd N3 O12'
_chemical_formula_weight         573.53

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'
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'

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

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

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

_cell_length_a                   13.9586(16)
_cell_length_b                   9.8262(12)
_cell_length_c                   17.3189(16)
_cell_angle_alpha                90
_cell_angle_beta                 127.699(6)
_cell_angle_gamma                90
_cell_volume                     1879.5(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    9901
_cell_measurement_theta_min      2.97
_cell_measurement_theta_max      27.45

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    2.027
_exptl_crystal_F_000             1116
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    3.601
_shelx_estimated_absorpt_T_min   0.715
_shelx_estimated_absorpt_T_max   0.762
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            48599
_diffrn_reflns_av_unetI/netI     0.0119
_diffrn_reflns_av_R_equivalents  0.0329
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.973
_diffrn_reflns_theta_max         25.007
_diffrn_reflns_theta_full        25.007
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3319
_reflns_number_gt                3026
_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       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0206P)²+3.4502P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3319
_refine_ls_number_parameters     272
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0221
_refine_ls_R_factor_gt           0.0185
_refine_ls_wR_factor_ref         0.0464
_refine_ls_wR_factor_gt          0.0443
_refine_ls_goodness_of_fit_ref   1.100
_refine_ls_restrained_S_all      1.162
_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
Gd1 Gd -0.50846(2) -0.04326(2) -0.64890(2) 0.01678(6) Uani 1 1 d . . . . .
O1 O -0.40021(19) -0.2319(2) -0.64054(15) 0.0212(4) Uani 1 1 d . . . . .
O2 O -0.4706(2) -0.4197(2) -0.72891(16) 0.0362(6) Uani 1 1 d . . . . .
O3 O -0.5071(2) -0.8352(2) -0.58497(15) 0.0266(5) Uani 1 1 d . . . . .
O4 O -0.4508(2) -0.8220(2) -0.43448(16) 0.0269(5) Uani 1 1 d . . . . .
O6 O -0.6502(2) -0.1933(2) -0.78684(16) 0.0354(6) Uani 1 1 d . . . . .
H6A H -0.7213 -0.1657 -0.8149 0.053 Uiso 1 1 d R U . . .
H6B H -0.6367 -0.2517 -0.8037 0.053 Uiso 1 1 d R U . . .
O7 O -0.3045(3) 0.0507(3) -0.5818(2) 0.0419(6) Uani 1 1 d . . . . .
O8 O -0.3168(2) -0.0403(2) -0.47530(17) 0.0321(5) Uani 1 1 d . . . . .
O9 O -0.7153(2) 0.0154(3) -0.71344(19) 0.0412(6) Uani 1 1 d . . . . .
H9A H -0.7575 -0.0556 -0.7325 0.062 Uiso 1 1 d R U . . .
H9B H -0.7125 0.0528 -0.6680 0.062 Uiso 1 1 d R U . . .
O10 O -0.1482(3) 0.0502(5) -0.4287(3) 0.0940(14) Uani 1 1 d . . . . .
N1 N -0.0673(3) -0.2663(3) -0.1099(2) 0.0370(7) Uani 1 1 d . . . . .
H1 H -0.0218 -0.2292 -0.0515 0.044 Uiso 1 1 d R U . . .
N2 N -0.2526(3) 0.0213(3) -0.4929(2) 0.0405(8) Uani 1 1 d . . . . .
C1 C -0.4179(3) -0.3574(3) -0.6491(2) 0.0189(6) Uani 1 1 d . . . . .
C2 C -0.3822(3) -0.4386(3) -0.5613(2) 0.0168(6) Uani 1 1 d . . . . .
C3 C -0.4277(3) -0.5689(3) -0.5727(2) 0.0177(6) Uani 1 1 d . . . . .
H3A H -0.4733 -0.6103 -0.6337 0.021 Uiso 1 1 calc R U . . .
C4 C -0.4049(2) -0.6371(3) -0.4929(2) 0.0162(6) Uani 1 1 d . . . . .
C5 C -0.3344(3) -0.5770(3) -0.4015(2) 0.0185(6) Uani 1 1 d . . . . .
H5B H -0.3199 -0.6232 -0.3483 0.022 Uiso 1 1 calc R U . . .
C6 C -0.2851(3) -0.4478(3) -0.3885(2) 0.0176(6) Uani 1 1 d . . . . .
C7 C -0.3103(3) -0.3790(3) -0.4693(2) 0.0176(6) Uani 1 1 d . . . . .
H7A H -0.2788 -0.2923 -0.4617 0.021 Uiso 1 1 calc R U . . .
C8 C -0.4582(3) -0.7757(3) -0.5052(2) 0.0179(6) Uani 1 1 d . . . . .
C9 C -0.2088(3) -0.3840(3) -0.2905(2) 0.0208(6) Uani 1 1 d . . . . .
C10 C -0.2255(3) -0.4146(4) -0.2210(2) 0.0374(9) Uani 1 1 d . . . . .
H10A H -0.2854 -0.4757 -0.2356 0.045 Uiso 1 1 calc R U . . .
C11 C -0.1533(4) -0.3543(5) -0.1310(3) 0.0488(11) Uani 1 1 d . . . . .
H11A H -0.1641 -0.3746 -0.0844 0.059 Uiso 1 1 calc R U . . .
C12 C -0.0471(3) -0.2318(4) -0.1738(2) 0.0292(7) Uani 1 1 d . . . . .
C13 C -0.1188(3) -0.2910(3) -0.2651(2) 0.0250(7) Uani 1 1 d . . . . .
H13A H -0.1066 -0.2682 -0.3106 0.030 Uiso 1 1 calc R U . . .
C14 C 0.0513(4) -0.1334(5) -0.1422(3) 0.0499(11) Uani 1 1 d . . . . .
H14A H 0.0861 -0.1019 -0.0775 0.075 Uiso 1 1 calc R U . . .
H14B H 0.0189 -0.0575 -0.1863 0.075 Uiso 1 1 calc R U . . .
H14C H 0.1127 -0.1772 -0.1424 0.075 Uiso 1 1 calc R U . . .
O11 O -0.0517(3) -0.2566(4) -0.4246(3) 0.0760(10) Uani 1 1 d . U . . .
O12 O 0.1128(3) -0.3103(4) -0.2857(2) 0.0654(10) Uani 1 1 d . . . . .
O13 O 0.1006(3) -0.3223(4) -0.41573(19) 0.0620(10) Uani 1 1 d . . . . .
N3 N 0.0539(3) -0.2947(4) -0.3746(2) 0.0474(9) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Gd1 O4 2.273(2) 3_444 ?
Gd1 O2 2.298(2) 2_453 ?
Gd1 O3 2.319(2) 1_565 ?
Gd1 O1 2.339(2) . ?
Gd1 O9 2.443(3) . ?
Gd1 O6 2.452(2) . ?
Gd1 O7 2.503(3) . ?
Gd1 O8 2.522(2) . ?
Gd1 N2 2.942(3) . ?
O1 C1 1.249(4) . ?
O2 C1 1.259(4) . ?
O2 Gd1 2.298(2) 2_443 ?
O3 C8 1.251(4) . ?
O3 Gd1 2.319(2) 1_545 ?
O4 C8 1.250(4) . ?
O4 Gd1 2.273(2) 3_444 ?
O6 H6A 0.8401 . ?
O6 H6B 0.7187 . ?
O7 N2 1.270(4) . ?
O8 N2 1.263(4) . ?
O9 H9A 0.8400 . ?
O9 H9B 0.8482 . ?
O10 N2 1.208(4) . ?
N1 C11 1.336(5) . ?
N1 C12 1.341(4) . ?
N1 H1 0.8800 . ?
C1 C2 1.506(4) . ?
C2 C3 1.389(4) . ?
C2 C7 1.391(4) . ?
C3 C4 1.386(4) . ?
C3 H3A 0.9300 . ?
C4 C5 1.385(4) . ?
C4 C8 1.503(4) . ?
C5 C6 1.396(4) . ?
C5 H5B 0.9300 . ?
C6 C7 1.391(4) . ?
C6 C9 1.482(4) . ?
C7 H7A 0.9300 . ?
C9 C13 1.389(4) . ?
C9 C10 1.392(4) . ?
C10 C11 1.370(5) . ?
C10 H10A 0.9300 . ?
C11 H11A 0.9300 . ?
C12 C13 1.380(4) . ?
C12 C14 1.484(5) . ?
C13 H13A 0.9300 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
O11 N3 1.226(5) . ?
O12 N3 1.234(4) . ?
O13 N3 1.254(4) . ?

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
O4 Gd1 O2 162.27(9) 3_444 2_453 ?
O4 Gd1 O3 98.19(8) 3_444 1_565 ?
O2 Gd1 O3 86.17(8) 2_453 1_565 ?
O4 Gd1 O1 84.39(8) 3_444 . ?
O2 Gd1 O1 100.90(8) 2_453 . ?
O3 Gd1 O1 148.46(8) 1_565 . ?
O4 Gd1 O9 75.13(9) 3_444 . ?
O2 Gd1 O9 90.28(10) 2_453 . ?
O3 Gd1 O9 70.92(8) 1_565 . ?
O1 Gd1 O9 138.86(8) . . ?
O4 Gd1 O6 84.41(8) 3_444 . ?
O2 Gd1 O6 81.26(9) 2_453 . ?
O3 Gd1 O6 139.57(8) 1_565 . ?
O1 Gd1 O6 71.93(8) . . ?
O9 Gd1 O6 70.88(8) . . ?
O4 Gd1 O7 125.14(9) 3_444 . ?
O2 Gd1 O7 72.56(10) 2_453 . ?
O3 Gd1 O7 77.19(8) 1_565 . ?
O1 Gd1 O7 75.82(8) . . ?
O9 Gd1 O7 144.68(9) . . ?
O6 Gd1 O7 133.23(9) . . ?
O4 Gd1 O8 75.21(8) 3_444 . ?
O2 Gd1 O8 122.43(9) 2_453 . ?
O3 Gd1 O8 74.18(8) 1_565 . ?
O1 Gd1 O8 76.19(7) . . ?
O9 Gd1 O8 129.65(8) . . ?
O6 Gd1 O8 143.52(8) . . ?
O7 Gd1 O8 50.64(9) . . ?
O4 Gd1 N2 100.21(9) 3_444 . ?
O2 Gd1 N2 97.51(10) 2_453 . ?
O3 Gd1 N2 73.76(9) 1_565 . ?
O1 Gd1 N2 74.85(8) . . ?
O9 Gd1 N2 143.18(9) . . ?
O6 Gd1 N2 145.83(8) . . ?
O7 Gd1 N2 25.38(9) . . ?
O8 Gd1 N2 25.27(9) . . ?
C1 O1 Gd1 134.5(2) . . ?
C1 O2 Gd1 158.2(2) . 2_443 ?
C8 O3 Gd1 141.21(19) . 1_545 ?
C8 O4 Gd1 158.7(2) . 3_444 ?
Gd1 O6 H6A 109.5 . . ?
Gd1 O6 H6B 128.3 . . ?
H6A O6 H6B 122.3 . . ?
N2 O7 Gd1 97.01(19) . . ?
N2 O8 Gd1 96.3(2) . . ?
Gd1 O9 H9A 109.5 . . ?
Gd1 O9 H9B 107.9 . . ?
H9A O9 H9B 110.3 . . ?
C11 N1 C12 123.0(3) . . ?
C11 N1 H1 118.6 . . ?
C12 N1 H1 118.4 . . ?
O10 N2 O8 121.6(4) . . ?
O10 N2 O7 122.4(4) . . ?
O8 N2 O7 116.0(3) . . ?
O10 N2 Gd1 178.8(3) . . ?
O8 N2 Gd1 58.45(16) . . ?
O7 N2 Gd1 57.61(16) . . ?
O1 C1 O2 123.4(3) . . ?
O1 C1 C2 119.0(3) . . ?
O2 C1 C2 117.5(3) . . ?
C3 C2 C7 119.9(3) . . ?
C3 C2 C1 120.3(3) . . ?
C7 C2 C1 119.7(3) . . ?
C4 C3 C2 119.9(3) . . ?
C4 C3 H3A 120.1 . . ?
C2 C3 H3A 120.1 . . ?
C5 C4 C3 120.2(3) . . ?
C5 C4 C8 119.5(3) . . ?
C3 C4 C8 120.3(3) . . ?
C4 C5 C6 120.5(3) . . ?
C4 C5 H5B 119.8 . . ?
C6 C5 H5B 119.8 . . ?
C7 C6 C5 118.9(3) . . ?
C7 C6 C9 120.6(3) . . ?
C5 C6 C9 120.5(3) . . ?
C2 C7 C6 120.6(3) . . ?
C2 C7 H7A 119.7 . . ?
C6 C7 H7A 119.7 . . ?
O4 C8 O3 125.1(3) . . ?
O4 C8 C4 117.0(3) . . ?
O3 C8 C4 117.9(3) . . ?
C13 C9 C10 117.7(3) . . ?
C13 C9 C6 121.2(3) . . ?
C10 C9 C6 121.1(3) . . ?
C11 C10 C9 119.7(3) . . ?
C11 C10 H10A 120.2 . . ?
C9 C10 H10A 120.2 . . ?
N1 C11 C10 120.3(3) . . ?
N1 C11 H11A 119.9 . . ?
C10 C11 H11A 119.9 . . ?
N1 C12 C13 117.9(3) . . ?
N1 C12 C14 118.3(3) . . ?
C13 C12 C14 123.8(3) . . ?
C12 C13 C9 121.5(3) . . ?
C12 C13 H13A 119.3 . . ?
C9 C13 H13A 119.3 . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O11 N3 O12 121.0(4) . . ?
O11 N3 O13 118.9(3) . . ?
O12 N3 O13 120.0(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Gd1 O8 N2 O10 178.6(4) . . . . ?
Gd1 O8 N2 O7 -1.5(3) . . . . ?
Gd1 O7 N2 O10 -178.6(4) . . . . ?
Gd1 O7 N2 O8 1.5(3) . . . . ?
Gd1 O1 C1 O2 90.9(4) . . . . ?
Gd1 O1 C1 C2 -85.0(3) . . . . ?
Gd1 O2 C1 O1 94.4(6) 2_443 . . . ?
Gd1 O2 C1 C2 -89.7(6) 2_443 . . . ?
O1 C1 C2 C3 163.3(3) . . . . ?
O2 C1 C2 C3 -12.9(4) . . . . ?
O1 C1 C2 C7 -12.1(4) . . . . ?
O2 C1 C2 C7 171.8(3) . . . . ?
C7 C2 C3 C4 2.3(4) . . . . ?
C1 C2 C3 C4 -173.0(3) . . . . ?
C2 C3 C4 C5 -1.6(4) . . . . ?
C2 C3 C4 C8 177.3(3) . . . . ?
C3 C4 C5 C6 -0.3(4) . . . . ?
C8 C4 C5 C6 -179.3(3) . . . . ?
C4 C5 C6 C7 1.5(4) . . . . ?
C4 C5 C6 C9 -179.5(3) . . . . ?
C3 C2 C7 C6 -1.1(4) . . . . ?
C1 C2 C7 C6 174.3(3) . . . . ?
C5 C6 C7 C2 -0.8(4) . . . . ?
C9 C6 C7 C2 -179.8(3) . . . . ?
Gd1 O4 C8 O3 -16.7(8) 3_444 . . . ?
Gd1 O4 C8 C4 162.7(4) 3_444 . . . ?
Gd1 O3 C8 O4 -49.9(5) 1_545 . . . ?
Gd1 O3 C8 C4 130.6(3) 1_545 . . . ?
C5 C4 C8 O4 10.2(4) . . . . ?
C3 C4 C8 O4 -168.8(3) . . . . ?
C5 C4 C8 O3 -170.3(3) . . . . ?
C3 C4 C8 O3 10.7(4) . . . . ?
C7 C6 C9 C13 -29.5(4) . . . . ?
C5 C6 C9 C13 151.5(3) . . . . ?
C7 C6 C9 C10 150.0(3) . . . . ?
C5 C6 C9 C10 -28.9(5) . . . . ?
C13 C9 C10 C11 -0.6(6) . . . . ?
C6 C9 C10 C11 179.8(4) . . . . ?
C12 N1 C11 C10 0.4(7) . . . . ?
C9 C10 C11 N1 0.1(7) . . . . ?
C11 N1 C12 C13 -0.2(6) . . . . ?
C11 N1 C12 C14 -179.8(4) . . . . ?
N1 C12 C13 C9 -0.3(5) . . . . ?
C14 C12 C13 C9 179.2(4) . . . . ?
C10 C9 C13 C12 0.7(5) . . . . ?
C6 C9 C13 C12 -179.7(3) . . . . ?

_refine_diff_density_max         0.917
_refine_diff_density_min         -0.778
_refine_diff_density_rms         0.088

