# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2016

####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1480852'
_audit_update_record             
;
2016-11-30 deposited with the CCDC.
2016-12-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H13 N O7 Zn'
_chemical_formula_weight         396.64

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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   7.9019(5)
_cell_length_b                   9.7220(6)
_cell_length_c                   10.8821(7)
_cell_angle_alpha                97.9470(10)
_cell_angle_beta                 95.9170(10)
_cell_angle_gamma                113.0620(10)
_cell_volume                     750.36(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3432
_cell_measurement_theta_min      0.930
_cell_measurement_theta_max      28.225

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.756
_exptl_crystal_F_000             404
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    1.679
_shelx_estimated_absorpt_T_min   0.633
_shelx_estimated_absorpt_T_max   0.730
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker SMART APEX CCD'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4735
_diffrn_reflns_av_unetI/netI     0.0310
_diffrn_reflns_av_R_equivalents  0.0145
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.918
_diffrn_reflns_theta_max         28.225
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.930
_diffrn_measured_fraction_theta_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.930
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.930
_diffrn_reflns_point_group_measured_fraction_full 0.990
_reflns_number_total             3432
_reflns_number_gt                2981
_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       ?
_computing_data_reduction        ?
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014 (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)+(0.0435P)²+0.3294P] 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         3432
_refine_ls_number_parameters     238
_refine_ls_number_restraints     7
_refine_ls_R_factor_all          0.0398
_refine_ls_R_factor_gt           0.0336
_refine_ls_wR_factor_ref         0.0857
_refine_ls_wR_factor_gt          0.0820
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.041
_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
Zn1 Zn 1.16808(3) 1.39362(3) 1.02354(3) 0.03107(10) Uani 1 1 d D . . . .
C1 C 0.6343(3) 1.1316(2) 0.8829(2) 0.0232(4) Uani 1 1 d . . . . .
C2 C 0.6980(3) 1.0215(2) 0.9064(2) 0.0242(4) Uani 1 1 d . . . . .
H2 H 0.8155 1.0497 0.9537 0.029 Uiso 1 1 calc R U . . .
C3 C 0.5834(3) 0.8686(2) 0.8582(2) 0.0242(4) Uani 1 1 d . . . . .
C4 C 0.4072(3) 0.8263(2) 0.7896(2) 0.0253(4) Uani 1 1 d . . . . .
H4 H 0.3307 0.7236 0.7594 0.030 Uiso 1 1 calc R U . . .
C5 C 0.3439(3) 0.9366(2) 0.76560(19) 0.0226(4) Uani 1 1 d . . . . .
C6 C 0.4592(3) 1.0901(2) 0.8126(2) 0.0240(4) Uani 1 1 d . . . . .
H6 H 0.4184 1.1647 0.7969 0.029 Uiso 1 1 calc R U . . .
C7 C 0.7564(3) 1.2960(2) 0.9343(2) 0.0263(4) Uani 1 1 d . . . . .
C8 C 0.6478(3) 0.7479(3) 0.8835(2) 0.0316(5) Uani 1 1 d . . . . .
C10 C 0.0642(3) 0.7624(3) 0.6108(2) 0.0366(6) Uani 1 1 d . . . . .
C11 C -0.1143(3) 0.7669(3) 0.5626(2) 0.0344(5) Uani 1 1 d . . . . .
C12 C -0.2642(4) 0.6578(3) 0.4758(3) 0.0464(7) Uani 1 1 d . . . . .
H12 H -0.2629 0.5656 0.4404 0.056 Uiso 1 1 calc R U . . .
C13 C -0.4151(4) 0.6916(4) 0.4442(3) 0.0510(7) Uani 1 1 d . . . . .
H13 H -0.5179 0.6211 0.3864 0.061 Uiso 1 1 calc R U . . .
C14 C -0.4154(4) 0.8290(4) 0.4975(3) 0.0477(7) Uani 1 1 d . . . . .
H14 H -0.5189 0.8491 0.4745 0.057 Uiso 1 1 calc R U . . .
C15 C -0.2648(3) 0.9385(4) 0.5846(2) 0.0412(6) Uani 1 1 d . . . . .
H15 H -0.2657 1.0310 0.6197 0.049 Uiso 1 1 calc R U . . .
C16 C -0.1138(3) 0.9041(3) 0.6170(2) 0.0302(5) Uani 1 1 d . . . . .
C17 C 0.0668(3) 0.9965(3) 0.7064(2) 0.0310(5) Uani 1 1 d . . . . .
H17A H 0.1364 1.0916 0.6807 0.037 Uiso 1 1 calc R U . . .
H17B H 0.0452 1.0184 0.7917 0.037 Uiso 1 1 calc R U . . .
N1 N 0.1643(2) 0.8954(2) 0.69643(18) 0.0271(4) Uani 1 1 d . . . . .
O1 O 0.7096(2) 1.39287(18) 0.89140(17) 0.0388(4) Uani 1 1 d . . . . .
O2 O 0.8961(2) 1.33018(18) 1.01786(16) 0.0336(4) Uani 1 1 d . . . . .
O3 O 0.8161(3) 0.7911(2) 0.9353(2) 0.0494(5) Uani 1 1 d . . . . .
O4 O 0.5427(3) 0.6123(2) 0.8563(2) 0.0611(6) Uani 1 1 d . . . . .
O5 O 0.1173(3) 0.6628(2) 0.5781(2) 0.0725(8) Uani 1 1 d . . . . .
O6 O 1.2106(3) 1.3889(2) 0.84655(19) 0.0458(4) Uani 1 1 d D . . . .
O7 O 0.9202(4) 0.3724(4) 0.6859(3) 0.0812(8) Uani 1 1 d D . . . .
H6B H 1.310(2) 1.459(4) 0.835(3) 0.122 Uiso 1 1 d D U . . .
H6A H 1.125(2) 1.390(5) 0.794(2) 0.122 Uiso 1 1 d D U . . .
H7A H 0.913(7) 0.384(6) 0.6095(16) 0.122 Uiso 1 1 d D U . . .
H7B H 0.880(7) 0.434(5) 0.723(4) 0.122 Uiso 1 1 d D U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Zn1 O1 1.9524(16) 2_787 ?
Zn1 O3 1.9571(17) 2_777 ?
Zn1 O2 1.9813(16) . ?
Zn1 O6 1.986(2) . ?
Zn1 C8 2.586(2) 2_777 ?
C1 C6 1.386(3) . ?
C1 C2 1.391(3) . ?
C1 C7 1.494(3) . ?
C2 C3 1.391(3) . ?
C3 C4 1.385(3) . ?
C3 C8 1.497(3) . ?
C4 C5 1.393(3) . ?
C5 C6 1.395(3) . ?
C5 N1 1.411(3) . ?
C7 O2 1.256(3) . ?
C7 O1 1.265(3) . ?
C8 O4 1.225(3) . ?
C8 O3 1.267(3) . ?
C8 Zn1 2.586(2) 2_777 ?
C10 O5 1.222(3) . ?
C10 N1 1.371(3) . ?
C10 C11 1.473(3) . ?
C11 C16 1.380(3) . ?
C11 C12 1.388(3) . ?
C12 C13 1.379(4) . ?
C13 C14 1.382(4) . ?
C14 C15 1.394(4) . ?
C15 C16 1.385(3) . ?
C16 C17 1.502(3) . ?
C17 N1 1.468(3) . ?
O1 Zn1 1.9524(16) 2_787 ?
O3 Zn1 1.9571(17) 2_777 ?

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
O1 Zn1 O3 132.27(8) 2_787 2_777 ?
O1 Zn1 O2 106.91(7) 2_787 . ?
O3 Zn1 O2 98.12(8) 2_777 . ?
O1 Zn1 O6 106.33(8) 2_787 . ?
O3 Zn1 O6 104.40(9) 2_777 . ?
O2 Zn1 O6 106.55(8) . . ?
O1 Zn1 C8 107.64(7) 2_787 2_777 ?
O3 Zn1 C8 28.31(7) 2_777 2_777 ?
O2 Zn1 C8 123.66(7) . 2_777 ?
O6 Zn1 C8 104.62(8) . 2_777 ?
C6 C1 C2 120.70(19) . . ?
C6 C1 C7 119.89(18) . . ?
C2 C1 C7 119.42(18) . . ?
C3 C2 C1 119.05(18) . . ?
C4 C3 C2 120.57(19) . . ?
C4 C3 C8 119.32(19) . . ?
C2 C3 C8 120.09(19) . . ?
C3 C4 C5 120.32(19) . . ?
C4 C5 C6 119.29(18) . . ?
C4 C5 N1 121.05(18) . . ?
C6 C5 N1 119.65(18) . . ?
C1 C6 C5 120.07(18) . . ?
O2 C7 O1 124.0(2) . . ?
O2 C7 C1 118.91(19) . . ?
O1 C7 C1 117.11(18) . . ?
O4 C8 O3 120.7(2) . . ?
O4 C8 C3 121.8(2) . . ?
O3 C8 C3 117.4(2) . . ?
O4 C8 Zn1 74.04(14) . 2_777 ?
O3 C8 Zn1 47.10(11) . 2_777 ?
C3 C8 Zn1 162.89(17) . 2_777 ?
O5 C10 N1 126.1(2) . . ?
O5 C10 C11 127.2(2) . . ?
N1 C10 C11 106.7(2) . . ?
C16 C11 C12 122.3(2) . . ?
C16 C11 C10 108.9(2) . . ?
C12 C11 C10 128.8(2) . . ?
C13 C12 C11 117.4(3) . . ?
C12 C13 C14 120.8(3) . . ?
C13 C14 C15 121.8(3) . . ?
C16 C15 C14 117.4(3) . . ?
C11 C16 C15 120.3(2) . . ?
C11 C16 C17 109.56(19) . . ?
C15 C16 C17 130.1(2) . . ?
N1 C17 C16 102.38(18) . . ?
C10 N1 C5 125.19(18) . . ?
C10 N1 C17 112.43(17) . . ?
C5 N1 C17 122.34(17) . . ?
C7 O1 Zn1 119.21(14) . 2_787 ?
C7 O2 Zn1 136.25(16) . . ?
C8 O3 Zn1 104.59(15) . 2_777 ?

_refine_diff_density_max         0.444
_refine_diff_density_min         -0.411
_refine_diff_density_rms         0.072

_shelxl_version_number           2014-3

####################################################################### 
# 
# 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_3
_database_code_depnum_ccdc_archive 'CCDC 1480854'
_audit_update_record             
;
2016-11-30 deposited with the CCDC.
2016-12-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H21 N3 O7 Zn'
_chemical_formula_weight         552.83

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'
Zn Zn 0.2839 1.4301 '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                   8.6847(5)
_cell_length_b                   18.8160(11)
_cell_length_c                   14.1392(9)
_cell_angle_alpha                90
_cell_angle_beta                 91.9200(10)
_cell_angle_gamma                90
_cell_volume                     2309.2(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4175
_cell_measurement_theta_min      0.997
_cell_measurement_theta_max      25.249

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.590
_exptl_crystal_F_000             1136
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.17
_exptl_absorpt_coefficient_mu    1.119
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker SMART APEX CCD'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10268
_diffrn_reflns_av_unetI/netI     0.0446
_diffrn_reflns_av_R_equivalents  0.0340
_diffrn_reflns_limit_h_min       -3
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.802
_diffrn_reflns_theta_max         25.249
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             4175
_reflns_number_gt                3131
_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 (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)+(0.0414P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4175
_refine_ls_number_parameters     347
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0550
_refine_ls_R_factor_gt           0.0350
_refine_ls_wR_factor_ref         0.0829
_refine_ls_wR_factor_gt          0.0773
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_restrained_S_all      1.016
_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
H1WA H 0.600(4) 0.7639(19) 0.568(2) 0.058(13) Uiso 1 1 d . . . . .
H1A H 0.461(4) 0.8397(18) 1.039(2) 0.066(12) Uiso 1 1 d . . . . .
Zn1 Zn 0.32303(3) 0.85009(2) 0.87950(2) 0.02717(11) Uani 1 1 d . . . . .
C1 C 0.4582(3) 0.71754(14) 0.83905(18) 0.0310(6) Uani 1 1 d . . . . .
C2 C 0.4474(3) 0.63767(13) 0.83732(19) 0.0281(6) Uani 1 1 d . . . . .
C3 C 0.5051(3) 0.59898(13) 0.76287(18) 0.0301(6) Uani 1 1 d . . . . .
H3 H 0.5542 0.6223 0.7144 0.036 Uiso 1 1 calc R U . . .
C4 C 0.4899(3) 0.52575(14) 0.76048(18) 0.0294(6) Uani 1 1 d . . . . .
C5 C 0.5508(3) 0.48307(14) 0.67980(19) 0.0312(6) Uani 1 1 d . . . . .
C6 C 0.4201(3) 0.49029(14) 0.83431(18) 0.0300(6) Uani 1 1 d . . . . .
H6 H 0.4117 0.4410 0.8332 0.036 Uiso 1 1 calc R U . . .
C7 C 0.3631(3) 0.52845(13) 0.90942(18) 0.0286(6) Uani 1 1 d . . . . .
C8 C 0.3761(3) 0.60207(13) 0.90955(18) 0.0287(6) Uani 1 1 d . . . . .
H8 H 0.3362 0.6279 0.9591 0.034 Uiso 1 1 calc R U . . .
C9 C 0.2028(3) 0.53731(13) 1.05275(18) 0.0334(7) Uani 1 1 d . . . . .
H9A H 0.1289 0.5688 1.0214 0.040 Uiso 1 1 calc R U . . .
H9B H 0.2737 0.5653 1.0920 0.040 Uiso 1 1 calc R U . . .
C10 C 0.2699(3) 0.42274(14) 1.00028(18) 0.0313(6) Uani 1 1 d . . . . .
C11 C 0.1672(3) 0.41576(14) 1.07998(18) 0.0319(6) Uani 1 1 d . . . . .
C12 C 0.1235(3) 0.48223(14) 1.10999(18) 0.0334(7) Uani 1 1 d . . . . .
C13 C 0.0193(3) 0.49066(16) 1.1803(2) 0.0437(8) Uani 1 1 d . . . . .
H13 H -0.0096 0.5357 1.2002 0.052 Uiso 1 1 calc R U . . .
C14 C -0.0414(4) 0.43006(17) 1.2208(2) 0.0492(8) Uani 1 1 d . . . . .
H14 H -0.1138 0.4344 1.2674 0.059 Uiso 1 1 calc R U . . .
C15 C 0.0048(4) 0.36317(17) 1.1924(2) 0.0516(9) Uani 1 1 d . . . . .
H15 H -0.0359 0.3232 1.2210 0.062 Uiso 1 1 calc R U . . .
C16 C 0.1104(4) 0.35479(16) 1.1224(2) 0.0429(7) Uani 1 1 d . . . . .
H16 H 0.1426 0.3098 1.1041 0.051 Uiso 1 1 calc R U . . .
C17 C 0.2300(4) 0.79855(14) 0.67104(19) 0.0398(7) Uani 1 1 d . . . . .
H17 H 0.3356 0.7974 0.6621 0.048 Uiso 1 1 calc R U . . .
C18 C 0.1324(4) 0.77482(17) 0.5994(2) 0.0477(8) Uani 1 1 d . . . . .
H18 H 0.1713 0.7580 0.5432 0.057 Uiso 1 1 calc R U . . .
C19 C -0.0232(4) 0.77634(17) 0.6122(2) 0.0512(8) Uani 1 1 d . . . . .
H19 H -0.0914 0.7597 0.5651 0.061 Uiso 1 1 calc R U . . .
C20 C -0.0776(4) 0.80266(15) 0.6954(2) 0.0451(8) Uani 1 1 d . . . . .
H20 H -0.1829 0.8048 0.7050 0.054 Uiso 1 1 calc R U . . .
C21 C 0.0270(3) 0.82600(14) 0.76479(19) 0.0318(6) Uani 1 1 d . . . . .
C22 C -0.0198(3) 0.85674(13) 0.85617(19) 0.0327(6) Uani 1 1 d . . . . .
C23 C -0.1721(3) 0.87187(18) 0.8752(2) 0.0507(9) Uani 1 1 d . . . . .
H23 H -0.2504 0.8612 0.8311 0.061 Uiso 1 1 calc R U . . .
C24 C -0.2057(4) 0.90277(19) 0.9601(3) 0.0610(10) Uani 1 1 d . . . . .
H24 H -0.3070 0.9139 0.9735 0.073 Uiso 1 1 calc R U . . .
C25 C -0.0894(4) 0.91700(18) 1.0245(2) 0.0534(9) Uani 1 1 d . . . . .
H25 H -0.1101 0.9378 1.0823 0.064 Uiso 1 1 calc R U . . .
C26 C 0.0592(3) 0.90004(16) 1.0024(2) 0.0430(8) Uani 1 1 d . . . . .
H26 H 0.1382 0.9092 1.0468 0.052 Uiso 1 1 calc R U . . .
N1 N 0.1793(3) 0.82336(12) 0.75344(15) 0.0326(5) Uani 1 1 d . . . . .
N2 N 0.0950(3) 0.87084(11) 0.91962(15) 0.0322(5) Uani 1 1 d . . . . .
N3 N 0.2853(3) 0.49480(11) 0.98386(15) 0.0310(5) Uani 1 1 d . . . . .
O1 O 0.4081(3) 0.87212(11) 1.01679(14) 0.0378(5) Uani 1 1 d . . . . .
H1B H 0.4492 0.9114 1.0178 0.057 Uiso 1 1 calc R U . . .
O2 O 0.5423(2) 0.74873(10) 0.78360(14) 0.0421(5) Uani 1 1 d . . . . .
O3 O 0.3738(2) 0.74872(9) 0.89841(12) 0.0370(5) Uani 1 1 d . . . . .
O4 O 0.5825(3) 0.51281(10) 0.60565(14) 0.0593(7) Uani 1 1 d . . . . .
O5 O 0.5624(2) 0.41694(9) 0.69467(13) 0.0411(5) Uani 1 1 d . . . . .
O6 O 0.3284(2) 0.37477(10) 0.95483(13) 0.0412(5) Uani 1 1 d . . . . .
O1W O 0.5919(3) 0.73014(14) 0.5939(2) 0.0522(6) Uani 1 1 d . . . . .
H1WB H 0.581(5) 0.735(2) 0.655(3) 0.13(2) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Zn1 O5 1.9347(18) 2_656 ?
Zn1 O3 1.9737(18) . ?
Zn1 O1 2.095(2) . ?
Zn1 N2 2.115(2) . ?
Zn1 N1 2.200(2) . ?
C1 O2 1.237(3) . ?
C1 O3 1.276(3) . ?
C1 C2 1.506(3) . ?
C2 C8 1.385(3) . ?
C2 C3 1.387(3) . ?
C3 C4 1.385(4) . ?
C4 C6 1.395(4) . ?
C4 C5 1.505(3) . ?
C5 O4 1.228(3) . ?
C5 O5 1.265(3) . ?
C6 C7 1.387(3) . ?
C7 C8 1.390(4) . ?
C7 N3 1.418(3) . ?
C9 N3 1.466(3) . ?
C9 C12 1.497(4) . ?
C10 O6 1.228(3) . ?
C10 N3 1.383(3) . ?
C10 C11 1.466(4) . ?
C11 C12 1.378(4) . ?
C11 C16 1.392(4) . ?
C12 C13 1.376(4) . ?
C13 C14 1.387(4) . ?
C14 C15 1.384(4) . ?
C15 C16 1.381(4) . ?
C17 N1 1.343(3) . ?
C17 C18 1.373(4) . ?
C18 C19 1.370(4) . ?
C19 C20 1.375(4) . ?
C20 C21 1.386(4) . ?
C21 N1 1.339(3) . ?
C21 C22 1.485(4) . ?
C22 N2 1.345(3) . ?
C22 C23 1.388(4) . ?
C23 C24 1.373(4) . ?
C24 C25 1.365(5) . ?
C25 C26 1.376(4) . ?
C26 N2 1.338(3) . ?
O5 Zn1 1.9347(18) 2_646 ?

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
O5 Zn1 O3 125.81(8) 2_656 . ?
O5 Zn1 O1 101.64(8) 2_656 . ?
O3 Zn1 O1 89.74(8) . . ?
O5 Zn1 N2 121.92(8) 2_656 . ?
O3 Zn1 N2 110.43(8) . . ?
O1 Zn1 N2 91.11(9) . . ?
O5 Zn1 N1 89.86(8) 2_656 . ?
O3 Zn1 N1 90.39(8) . . ?
O1 Zn1 N1 165.67(8) . . ?
N2 Zn1 N1 75.44(8) . . ?
O2 C1 O3 124.3(2) . . ?
O2 C1 C2 120.1(2) . . ?
O3 C1 C2 115.6(2) . . ?
C8 C2 C3 119.2(2) . . ?
C8 C2 C1 120.0(2) . . ?
C3 C2 C1 120.8(2) . . ?
C4 C3 C2 120.3(2) . . ?
C3 C4 C6 120.1(2) . . ?
C3 C4 C5 120.9(2) . . ?
C6 C4 C5 119.0(2) . . ?
O4 C5 O5 124.8(2) . . ?
O4 C5 C4 119.9(2) . . ?
O5 C5 C4 115.3(2) . . ?
C7 C6 C4 120.1(2) . . ?
C6 C7 C8 119.1(2) . . ?
C6 C7 N3 121.9(2) . . ?
C8 C7 N3 119.0(2) . . ?
C2 C8 C7 121.3(2) . . ?
N3 C9 C12 103.0(2) . . ?
O6 C10 N3 126.1(2) . . ?
O6 C10 C11 127.5(2) . . ?
N3 C10 C11 106.4(2) . . ?
C12 C11 C16 120.7(3) . . ?
C12 C11 C10 109.6(2) . . ?
C16 C11 C10 129.6(3) . . ?
C13 C12 C11 121.4(3) . . ?
C13 C12 C9 129.5(3) . . ?
C11 C12 C9 109.0(2) . . ?
C12 C13 C14 118.1(3) . . ?
C15 C14 C13 120.7(3) . . ?
C16 C15 C14 121.2(3) . . ?
C15 C16 C11 117.9(3) . . ?
N1 C17 C18 122.7(3) . . ?
C19 C18 C17 118.9(3) . . ?
C18 C19 C20 119.3(3) . . ?
C19 C20 C21 119.0(3) . . ?
N1 C21 C20 122.0(3) . . ?
N1 C21 C22 114.8(2) . . ?
C20 C21 C22 123.2(3) . . ?
N2 C22 C23 121.3(3) . . ?
N2 C22 C21 116.0(2) . . ?
C23 C22 C21 122.6(3) . . ?
C24 C23 C22 119.2(3) . . ?
C25 C24 C23 119.5(3) . . ?
C24 C25 C26 118.8(3) . . ?
N2 C26 C25 122.7(3) . . ?
C21 N1 C17 118.1(3) . . ?
C21 N1 Zn1 115.49(18) . . ?
C17 N1 Zn1 126.1(2) . . ?
C26 N2 C22 118.4(2) . . ?
C26 N2 Zn1 123.8(2) . . ?
C22 N2 Zn1 117.68(17) . . ?
C10 N3 C7 127.8(2) . . ?
C10 N3 C9 111.8(2) . . ?
C7 N3 C9 120.3(2) . . ?
C1 O3 Zn1 119.08(17) . . ?
C5 O5 Zn1 126.07(17) . 2_646 ?

_refine_diff_density_max         0.349
_refine_diff_density_min         -0.357
_refine_diff_density_rms         0.058

_shelxl_version_number           2014-3

####################################################################### 
# 
# 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 1480855'
_audit_update_record             
;
2016-11-30 deposited with the CCDC.
2016-12-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H13 N2 O5 S0 Zn'
_chemical_formula_weight         438.70

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

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

_cell_length_a                   24.119(4)
_cell_length_b                   7.7940(12)
_cell_length_c                   18.090(3)
_cell_angle_alpha                90
_cell_angle_beta                 100.985(2)
_cell_angle_gamma                90
_cell_volume                     3338.3(9)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2936
_cell_measurement_theta_min      1
_cell_measurement_theta_max      25

_exptl_crystal_description       prism
_exptl_crystal_colour            pink
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.746
_exptl_crystal_F_000             1784
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.16
_exptl_absorpt_coefficient_mu    1.512
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker SMART APEX CCD'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8184
_diffrn_reflns_av_unetI/netI     0.0778
_diffrn_reflns_av_R_equivalents  0.0663
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.720
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 0.969
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 0.969
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 0.969
_reflns_number_total             2936
_reflns_number_gt                1867
_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 (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)+(0.0119P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2936
_refine_ls_number_parameters     262
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0871
_refine_ls_R_factor_gt           0.0409
_refine_ls_wR_factor_ref         0.0683
_refine_ls_wR_factor_gt          0.0625
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_restrained_S_all      1.051
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Zn1 Zn 0.26428(2) 0.20792(6) 0.21676(2) 0.02882(14) Uani 1 1 d . . . . .
C2 C 0.21216(15) 0.4985(4) 0.53114(18) 0.0261(9) Uani 1 1 d . . . . .
C3 C 0.23706(14) 0.4750(4) 0.4690(2) 0.0274(9) Uani 1 1 d . . . . .
H3 H 0.2722 0.5232 0.4679 0.033 Uiso 1 1 calc R U . . .
C4 C 0.20957(14) 0.3798(4) 0.40854(18) 0.0251(9) Uani 1 1 d . . . . .
C5 C 0.23540(15) 0.3532(5) 0.3407(2) 0.0280(9) Uani 1 1 d . . . . .
C6 C 0.15685(14) 0.3116(5) 0.40919(19) 0.0298(9) Uani 1 1 d . . . . .
H6 H 0.1393 0.2435 0.3693 0.036 Uiso 1 1 calc R U . . .
C7 C 0.12984(15) 0.3441(4) 0.46909(19) 0.0267(9) Uani 1 1 d . . . . .
C8 C 0.15892(15) 0.4346(4) 0.53047(19) 0.0304(10) Uani 1 1 d . . . . .
H8 H 0.1421 0.4524 0.5720 0.037 Uiso 1 1 calc R U . . .
C9 C 0.04847(14) 0.3043(5) 0.53521(19) 0.0364(10) Uani 1 1 d . . . . .
H9A H 0.0485 0.4219 0.5528 0.044 Uiso 1 1 calc R U . . .
H9B H 0.0682 0.2327 0.5756 0.044 Uiso 1 1 calc R U . . .
C10 C 0.03567(16) 0.2357(5) 0.4059(2) 0.0321(10) Uani 1 1 d . . . . .
C11 C -0.01761(15) 0.2038(5) 0.4323(2) 0.0315(9) Uani 1 1 d . . . . .
C12 C -0.01026(15) 0.2414(5) 0.5077(2) 0.0335(10) Uani 1 1 d . . . . .
C13 C -0.05447(17) 0.2209(6) 0.5450(2) 0.0516(12) Uani 1 1 d . . . . .
H13 H -0.0503 0.2487 0.5957 0.062 Uiso 1 1 calc R U . . .
C14 C -0.10488(17) 0.1586(5) 0.5058(3) 0.0557(13) Uani 1 1 d . . . . .
H14 H -0.1347 0.1414 0.5310 0.067 Uiso 1 1 calc R U . . .
C15 C -0.11232(17) 0.1208(5) 0.4298(3) 0.0524(12) Uani 1 1 d . . . . .
H15 H -0.1469 0.0799 0.4042 0.063 Uiso 1 1 calc R U . . .
C16 C -0.06827(17) 0.1439(5) 0.3922(2) 0.0419(11) Uani 1 1 d . . . . .
H16 H -0.0726 0.1198 0.3410 0.050 Uiso 1 1 calc R U . . .
C17 C 0.38273(16) 0.0578(5) 0.26241(19) 0.0315(10) Uani 1 1 d . . . . .
H17 H 0.3646 -0.0419 0.2731 0.038 Uiso 1 1 calc R U . . .
C18 C 0.44007(15) 0.0520(5) 0.26465(18) 0.0300(9) Uani 1 1 d . . . . .
H18 H 0.4595 -0.0508 0.2755 0.036 Uiso 1 1 calc R U . . .
C19 C 0.46909(13) 0.1992(5) 0.25066(18) 0.0276(8) Uani 1 1 d . . . . .
C20 C 0.43708(16) 0.3475(5) 0.23592(19) 0.0323(10) Uani 1 1 d . . . . .
H20 H 0.4544 0.4504 0.2275 0.039 Uiso 1 1 calc R U . . .
C21 C 0.37989(16) 0.3429(5) 0.23374(19) 0.0333(10) Uani 1 1 d . . . . .
H21 H 0.3595 0.4442 0.2235 0.040 Uiso 1 1 calc R U . . .
C1A C 0.24121(17) 0.6040(5) 0.5973(2) 0.0320(10) Uani 1 1 d . . . . .
N1 N 0.07393(12) 0.2914(4) 0.46816(15) 0.0324(7) Uani 1 1 d . . . . .
N2 N 0.35183(11) 0.1999(4) 0.24561(14) 0.0289(7) Uani 1 1 d . . . . .
O1 O 0.26318(10) 0.4734(3) 0.31781(12) 0.0330(7) Uani 1 1 d . . . . .
O2 O 0.22765(10) 0.2116(4) 0.30667(12) 0.0340(6) Uani 1 1 d . . . . .
O4 O 0.21401(10) 0.6336(3) 0.64996(13) 0.0387(7) Uani 1 1 d . . . . .
O5 O 0.04402(10) 0.2174(3) 0.34190(14) 0.0472(7) Uani 1 1 d . . . . .
O3A O 0.28917(11) 0.6599(3) 0.59846(14) 0.0495(8) 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
Zn1 O4 1.974(2) 6_565 ?
Zn1 O2 1.994(2) . ?
Zn1 O1 2.003(2) 4_545 ?
Zn1 N2 2.077(3) . ?
Zn1 C1A 2.583(4) 6_565 ?
C2 C3 1.384(4) . ?
C2 C8 1.375(4) . ?
C2 C1A 1.510(5) . ?
C3 C4 1.382(4) . ?
C3 H3 0.9300 . ?
C4 C6 1.380(4) . ?
C4 C5 1.493(5) . ?
C5 O2 1.260(4) . ?
C5 O1 1.267(4) . ?
C6 C7 1.390(4) . ?
C6 H6 0.9300 . ?
C7 C8 1.388(4) . ?
C7 N1 1.406(4) . ?
C8 H8 0.9300 . ?
C9 N1 1.464(4) . ?
C9 C12 1.492(5) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 O5 1.220(4) . ?
C10 N1 1.383(4) . ?
C10 C11 1.475(5) . ?
C11 C12 1.373(4) . ?
C11 C16 1.378(5) . ?
C12 C13 1.375(5) . ?
C13 C14 1.374(5) . ?
C13 H13 0.9300 . ?
C14 C15 1.384(5) . ?
C14 H14 0.9300 . ?
C15 C16 1.379(5) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C17 N2 1.337(4) . ?
C17 C18 1.377(4) . ?
C17 H17 0.9300 . ?
C18 C19 1.392(5) . ?
C18 H18 0.9300 . ?
C19 C20 1.387(5) . ?
C19 C19 1.496(6) 2_655 ?
C20 C21 1.373(5) . ?
C20 H20 0.9300 . ?
C21 N2 1.343(4) . ?
C21 H21 0.9300 . ?
C1A O3A 1.232(4) . ?
C1A O4 1.277(4) . ?
C1A Zn1 2.583(4) 6_566 ?
O1 Zn1 2.003(2) 4 ?
O4 Zn1 1.974(2) 6_566 ?

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 Zn1 O2 100.06(10) 6_565 . ?
O4 Zn1 O1 104.60(10) 6_565 4_545 ?
O2 Zn1 O1 95.52(10) . 4_545 ?
O4 Zn1 N2 130.46(11) 6_565 . ?
O2 Zn1 N2 112.50(10) . . ?
O1 Zn1 N2 108.09(11) 4_545 . ?
O4 Zn1 C1A 28.78(10) 6_565 6_565 ?
O2 Zn1 C1A 128.06(12) . 6_565 ?
O1 Zn1 C1A 104.53(10) 4_545 6_565 ?
N2 Zn1 C1A 105.90(12) . 6_565 ?
C3 C2 C8 119.6(3) . . ?
C3 C2 C1A 120.5(3) . . ?
C8 C2 C1A 119.7(3) . . ?
C4 C3 C2 119.8(3) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
C3 C4 C6 120.3(3) . . ?
C3 C4 C5 120.8(3) . . ?
C6 C4 C5 118.9(3) . . ?
O2 C5 O1 121.8(3) . . ?
O2 C5 C4 118.5(3) . . ?
O1 C5 C4 119.7(4) . . ?
C7 C6 C4 120.4(3) . . ?
C7 C6 H6 119.8 . . ?
C4 C6 H6 119.8 . . ?
C8 C7 C6 118.4(3) . . ?
C8 C7 N1 119.7(3) . . ?
C6 C7 N1 121.9(3) . . ?
C7 C8 C2 121.3(3) . . ?
C7 C8 H8 119.3 . . ?
C2 C8 H8 119.3 . . ?
N1 C9 C12 102.9(3) . . ?
N1 C9 H9A 111.2 . . ?
C12 C9 H9A 111.2 . . ?
N1 C9 H9B 111.2 . . ?
C12 C9 H9B 111.2 . . ?
H9A C9 H9B 109.1 . . ?
O5 C10 N1 127.2(3) . . ?
O5 C10 C11 126.8(3) . . ?
N1 C10 C11 106.0(3) . . ?
C12 C11 C16 122.0(3) . . ?
C12 C11 C10 109.3(3) . . ?
C16 C11 C10 128.8(4) . . ?
C11 C12 C13 119.8(4) . . ?
C11 C12 C9 109.6(3) . . ?
C13 C12 C9 130.6(4) . . ?
C14 C13 C12 118.8(4) . . ?
C14 C13 H13 120.6 . . ?
C12 C13 H13 120.6 . . ?
C13 C14 C15 121.4(4) . . ?
C13 C14 H14 119.3 . . ?
C15 C14 H14 119.3 . . ?
C16 C15 C14 119.8(4) . . ?
C16 C15 H15 120.1 . . ?
C14 C15 H15 120.1 . . ?
C15 C16 C11 118.2(4) . . ?
C15 C16 H16 120.9 . . ?
C11 C16 H16 120.9 . . ?
N2 C17 C18 123.2(4) . . ?
N2 C17 H17 118.4 . . ?
C18 C17 H17 118.4 . . ?
C17 C18 C19 120.3(3) . . ?
C17 C18 H18 119.9 . . ?
C19 C18 H18 119.9 . . ?
C18 C19 C20 116.2(3) . . ?
C18 C19 C19 122.7(2) . 2_655 ?
C20 C19 C19 121.1(2) . 2_655 ?
C21 C20 C19 120.2(3) . . ?
C21 C20 H20 119.9 . . ?
C19 C20 H20 119.9 . . ?
N2 C21 C20 123.5(3) . . ?
N2 C21 H21 118.3 . . ?
C20 C21 H21 118.3 . . ?
O3A C1A O4 122.5(4) . . ?
O3A C1A C2 119.9(4) . . ?
O4 C1A C2 117.6(3) . . ?
O3A C1A Zn1 74.5(2) . 6_566 ?
O4 C1A Zn1 48.10(17) . 6_566 ?
C2 C1A Zn1 164.9(3) . 6_566 ?
C10 N1 C7 126.2(3) . . ?
C10 N1 C9 112.1(3) . . ?
C7 N1 C9 121.5(3) . . ?
C17 N2 C21 116.6(3) . . ?
C17 N2 Zn1 125.3(3) . . ?
C21 N2 Zn1 117.0(3) . . ?
C5 O1 Zn1 127.8(2) . 4 ?
C5 O2 Zn1 111.3(2) . . ?
C1A O4 Zn1 103.1(2) . 6_566 ?

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
C8 C2 C3 C4 -3.5(5) . . . . ?
C1A C2 C3 C4 -179.2(3) . . . . ?
C2 C3 C4 C6 1.6(5) . . . . ?
C2 C3 C4 C5 179.8(3) . . . . ?
C3 C4 C5 O2 144.8(3) . . . . ?
C6 C4 C5 O2 -37.0(5) . . . . ?
C3 C4 C5 O1 -36.9(5) . . . . ?
C6 C4 C5 O1 141.3(4) . . . . ?
C3 C4 C6 C7 2.8(5) . . . . ?
C5 C4 C6 C7 -175.5(3) . . . . ?
C4 C6 C7 C8 -5.0(5) . . . . ?
C4 C6 C7 N1 173.5(3) . . . . ?
C6 C7 C8 C2 3.1(5) . . . . ?
N1 C7 C8 C2 -175.5(3) . . . . ?
C3 C2 C8 C7 1.2(5) . . . . ?
C1A C2 C8 C7 176.9(3) . . . . ?
O5 C10 C11 C12 -179.2(4) . . . . ?
N1 C10 C11 C12 0.5(4) . . . . ?
O5 C10 C11 C16 1.6(7) . . . . ?
N1 C10 C11 C16 -178.7(4) . . . . ?
C16 C11 C12 C13 -0.6(6) . . . . ?
C10 C11 C12 C13 -179.8(3) . . . . ?
C16 C11 C12 C9 -179.6(4) . . . . ?
C10 C11 C12 C9 1.2(4) . . . . ?
N1 C9 C12 C11 -2.2(4) . . . . ?
N1 C9 C12 C13 178.9(4) . . . . ?
C11 C12 C13 C14 1.6(6) . . . . ?
C9 C12 C13 C14 -179.6(4) . . . . ?
C12 C13 C14 C15 -1.7(7) . . . . ?
C13 C14 C15 C16 0.7(7) . . . . ?
C14 C15 C16 C11 0.4(6) . . . . ?
C12 C11 C16 C15 -0.5(6) . . . . ?
C10 C11 C16 C15 178.6(4) . . . . ?
N2 C17 C18 C19 1.4(5) . . . . ?
C17 C18 C19 C20 0.9(5) . . . . ?
C17 C18 C19 C19 -177.6(4) . . . 2_655 ?
C18 C19 C20 C21 -1.7(5) . . . . ?
C19 C19 C20 C21 176.8(4) 2_655 . . . ?
C19 C20 C21 N2 0.3(5) . . . . ?
C3 C2 C1A O3A -5.1(5) . . . . ?
C8 C2 C1A O3A 179.2(3) . . . . ?
C3 C2 C1A O4 174.0(3) . . . . ?
C8 C2 C1A O4 -1.7(5) . . . . ?
C3 C2 C1A Zn1 157.5(8) . . . 6_566 ?
C8 C2 C1A Zn1 -18.2(11) . . . 6_566 ?
O5 C10 N1 C7 2.5(6) . . . . ?
C11 C10 N1 C7 -177.1(3) . . . . ?
O5 C10 N1 C9 177.7(4) . . . . ?
C11 C10 N1 C9 -1.9(4) . . . . ?
C8 C7 N1 C10 164.6(3) . . . . ?
C6 C7 N1 C10 -13.9(6) . . . . ?
C8 C7 N1 C9 -10.2(5) . . . . ?
C6 C7 N1 C9 171.3(3) . . . . ?
C12 C9 N1 C10 2.6(4) . . . . ?
C12 C9 N1 C7 178.0(3) . . . . ?
C18 C17 N2 C21 -2.8(5) . . . . ?
C18 C17 N2 Zn1 164.9(3) . . . . ?
C20 C21 N2 C17 2.0(5) . . . . ?
C20 C21 N2 Zn1 -166.8(3) . . . . ?
O2 C5 O1 Zn1 117.9(3) . . . 4 ?
C4 C5 O1 Zn1 -60.4(4) . . . 4 ?
O1 C5 O2 Zn1 0.2(4) . . . . ?
C4 C5 O2 Zn1 178.5(2) . . . . ?
O3A C1A O4 Zn1 4.7(4) . . . 6_566 ?
C2 C1A O4 Zn1 -174.3(2) . . . 6_566 ?

_refine_diff_density_max         0.354
_refine_diff_density_min         -0.338
_refine_diff_density_rms         0.078

_shelxl_version_number           2014-3

####################################################################### 
# 
# 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 1497047'
_audit_update_record             
;
2016-11-30 deposited with the CCDC.
2016-12-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H20.50 Cu N1.50 O9'
_chemical_formula_weight         465.40

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'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      trigonal
_space_group_IT_number           148
_space_group_name_H-M_alt        'R -3 :H'
_space_group_name_Hall           '-R 3'

_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'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'

_cell_length_a                   21.187(10)
_cell_length_b                   21.187(10)
_cell_length_c                   21.90(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     8516(12)
_cell_formula_units_Z            18
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3333
_cell_measurement_theta_min      1.001
_cell_measurement_theta_max      24.987

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.634
_exptl_crystal_F_000             4320
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    1.209
_shelx_estimated_absorpt_T_min   0.794
_shelx_estimated_absorpt_T_max   0.942
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker SMART APEX CCD'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12643
_diffrn_reflns_av_unetI/netI     0.1137
_diffrn_reflns_av_R_equivalents  0.0960
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         1.448
_diffrn_reflns_theta_max         24.987
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 0.972
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 0.972
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 0.972
_reflns_number_total             3333
_reflns_number_gt                2118
_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.
 
 Structure factors included contributions from the .fab file.
 
 _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 (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)+(0.0007P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3333
_refine_ls_number_parameters     233
_refine_ls_number_restraints     11
_refine_ls_R_factor_all          0.0826
_refine_ls_R_factor_gt           0.0510
_refine_ls_wR_factor_ref         0.1078
_refine_ls_wR_factor_gt          0.0992
_refine_ls_goodness_of_fit_ref   0.947
_refine_ls_restrained_S_all      0.948
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.46954(3) 0.53956(3) 0.00938(2) 0.02710(17) Uani 1 1 d . . . . .
C1 C 0.4055(2) 0.4027(2) 0.06821(19) 0.0316(11) Uani 1 1 d . . . . .
C2 C 0.3492(2) 0.3429(2) 0.10711(18) 0.0303(10) Uani 1 1 d . . . . .
C3 C 0.3132(2) 0.3580(2) 0.15293(18) 0.0299(10) Uani 1 1 d . . . . .
H3 H 0.3234 0.4055 0.1597 0.036 Uiso 1 1 calc R U . . .
C4 C 0.2622(2) 0.3015(2) 0.18829(18) 0.0303(10) Uani 1 1 d . . . . .
C5 C 0.2451(2) 0.2311(2) 0.1765(2) 0.0353(11) Uani 1 1 d . . . . .
H5 H 0.2094 0.1934 0.1996 0.042 Uiso 1 1 calc R U . . .
C6 C 0.2799(2) 0.2151(2) 0.13091(19) 0.0326(11) Uani 1 1 d . . . . .
C7 C 0.3330(2) 0.2719(2) 0.09693(19) 0.0345(11) Uani 1 1 d . . . . .
H7 H 0.3581 0.2622 0.0669 0.041 Uiso 1 1 calc R U . . .
C8 C 0.2965(3) 0.1194(3) 0.0791(2) 0.0419(12) Uani 1 1 d D . . . .
H8A H 0.3470 0.1387 0.0910 0.050 Uiso 0.222(10) 1 calc R U P A 2
H8B H 0.2949 0.1353 0.0380 0.050 Uiso 0.222(10) 1 calc R U P A 2
C9 C 0.2555(3) 0.0387(2) 0.0833(2) 0.0393(12) Uani 1 1 d . . . . .
C10 C 0.2685(3) -0.0093(3) 0.0522(2) 0.0558(15) Uani 1 1 d . . . . .
H10 H 0.3059 0.0065 0.0237 0.067 Uiso 1 1 calc R U . . .
C11 C 0.2241(4) -0.0821(3) 0.0647(3) 0.0729(19) Uani 1 1 d . . . . .
H11 H 0.2311 -0.1163 0.0439 0.087 Uiso 1 1 calc R U . . .
C12 C 0.1702(3) -0.1050(3) 0.1069(3) 0.0706(18) Uani 1 1 d . . . . .
H12 H 0.1415 -0.1546 0.1150 0.085 Uiso 1 1 calc R U . . .
C13 C 0.1572(3) -0.0559(3) 0.1382(3) 0.0641(16) Uani 1 1 d . . . . .
H13 H 0.1201 -0.0716 0.1669 0.077 Uiso 1 1 calc R U . . .
C14 C 0.2014(3) 0.0173(3) 0.1254(2) 0.0475(13) Uani 1 1 d . . . . .
C15 C 0.2023(3) 0.0808(2) 0.1520(2) 0.0465(14) Uani 1 1 d D . . . .
H15A H 0.1561 0.0788 0.1457 0.056 Uiso 0.778(10) 1 calc R U P A 1
H15B H 0.2121 0.0836 0.1955 0.056 Uiso 0.778(10) 1 calc R U P A 1
C16 C 0.4222(2) 0.4390(2) -0.09186(18) 0.0318(11) Uani 1 1 d . . . . .
N1 N 0.26011(19) 0.14207(18) 0.12055(16) 0.0395(10) Uani 1 1 d D . . . .
O1 O 0.54945(15) 0.61027(15) -0.04255(13) 0.0363(8) Uani 1 1 d . . . . .
O2 O 0.4168(3) 0.6027(2) 0.0193(2) 0.0813(13) Uani 1 1 d D . . . .
O3 O 0.53265(16) 0.58054(16) 0.08005(12) 0.0382(8) Uani 1 1 d . . . . .
O4 O 0.40133(15) 0.45866(16) 0.06189(14) 0.0365(8) Uani 1 1 d . . . . .
O5 O 0.41411(16) 0.48600(16) -0.06245(13) 0.0386(8) Uani 1 1 d . . . . .
H2A H 0.412(2) 0.6172(19) -0.0156(9) 0.046 Uiso 1 1 d D U . . .
H2B H 0.441(2) 0.6396(14) 0.0425(13) 0.046 Uiso 1 1 d D U . . .
O6 O 0.3497(2) 0.1568(2) 0.05084(19) 0.0479(18) Uani 0.778(10) 1 d . . P A 1
O6A O 0.1704(13) 0.0810(11) 0.1905(11) 0.110(10) Uani 0.222(10) 1 d . U P A 2


_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
Cu1 O3 1.943(3) . ?
Cu1 O5 1.952(3) . ?
Cu1 O1 1.967(3) . ?
Cu1 O4 1.968(3) . ?
Cu1 O2 2.140(4) . ?
Cu1 Cu1 2.6094(16) 10_665 ?
C1 O4 1.241(5) . ?
C1 O1 1.250(5) 10_665 ?
C1 C2 1.498(6) . ?
C2 C7 1.383(6) . ?
C2 C3 1.391(5) . ?
C3 C4 1.381(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.373(6) . ?
C4 C16 1.493(6) 5 ?
C5 C6 1.379(6) . ?
C5 H5 0.9300 . ?
C6 C7 1.383(6) . ?
C6 N1 1.405(5) . ?
C7 H7 0.9300 . ?
C8 O6 1.179(5) . ?
C8 N1 1.421(4) . ?
C8 C9 1.483(6) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C14 1.359(6) . ?
C9 C10 1.364(6) . ?
C10 C11 1.374(7) . ?
C10 H10 0.9300 . ?
C11 C12 1.356(8) . ?
C11 H11 0.9300 . ?
C12 C13 1.385(7) . ?
C12 H12 0.9300 . ?
C13 C14 1.381(6) . ?
C13 H13 0.9300 . ?
C14 C15 1.458(7) . ?
C15 O6A 1.08(2) . ?
C15 N1 1.439(4) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 O3 1.245(5) 10_665 ?
C16 O5 1.267(5) . ?
C16 C4 1.493(6) 9_554 ?
O1 C1 1.250(5) 10_665 ?
O2 H2A 0.847(10) . ?
O2 H2B 0.856(10) . ?
O3 C16 1.245(5) 10_665 ?

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
O3 Cu1 O5 168.92(12) . . ?
O3 Cu1 O1 88.99(14) . . ?
O5 Cu1 O1 90.87(14) . . ?
O3 Cu1 O4 88.01(14) . . ?
O5 Cu1 O4 89.91(14) . . ?
O1 Cu1 O4 168.27(12) . . ?
O3 Cu1 O2 95.60(16) . . ?
O5 Cu1 O2 95.43(15) . . ?
O1 Cu1 O2 95.84(15) . . ?
O4 Cu1 O2 95.74(15) . . ?
O3 Cu1 Cu1 87.80(9) . 10_665 ?
O5 Cu1 Cu1 81.18(9) . 10_665 ?
O1 Cu1 Cu1 83.36(9) . 10_665 ?
O4 Cu1 Cu1 85.20(9) . 10_665 ?
O2 Cu1 Cu1 176.49(13) . 10_665 ?
O4 C1 O1 125.9(4) . 10_665 ?
O4 C1 C2 117.7(4) . . ?
O1 C1 C2 116.3(4) 10_665 . ?
C7 C2 C3 120.0(4) . . ?
C7 C2 C1 119.2(4) . . ?
C3 C2 C1 120.8(4) . . ?
C4 C3 C2 119.1(4) . . ?
C4 C3 H3 120.4 . . ?
C2 C3 H3 120.4 . . ?
C5 C4 C3 120.2(4) . . ?
C5 C4 C16 119.2(4) . 5 ?
C3 C4 C16 120.6(4) . 5 ?
C4 C5 C6 121.3(4) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 H5 119.3 . . ?
C5 C6 C7 118.6(4) . . ?
C5 C6 N1 119.0(4) . . ?
C7 C6 N1 122.4(4) . . ?
C2 C7 C6 120.7(4) . . ?
C2 C7 H7 119.7 . . ?
C6 C7 H7 119.7 . . ?
O6 C8 N1 127.3(4) . . ?
O6 C8 C9 128.3(4) . . ?
N1 C8 C9 104.2(4) . . ?
N1 C8 H8A 110.9 . . ?
C9 C8 H8A 110.9 . . ?
N1 C8 H8B 110.9 . . ?
C9 C8 H8B 110.9 . . ?
H8A C8 H8B 108.9 . . ?
C14 C9 C10 122.7(5) . . ?
C14 C9 C8 109.7(4) . . ?
C10 C9 C8 127.5(5) . . ?
C9 C10 C11 117.2(5) . . ?
C9 C10 H10 121.4 . . ?
C11 C10 H10 121.4 . . ?
C12 C11 C10 121.3(6) . . ?
C12 C11 H11 119.4 . . ?
C10 C11 H11 119.4 . . ?
C11 C12 C13 121.1(5) . . ?
C11 C12 H12 119.5 . . ?
C13 C12 H12 119.5 . . ?
C14 C13 C12 117.8(5) . . ?
C14 C13 H13 121.1 . . ?
C12 C13 H13 121.1 . . ?
C9 C14 C13 119.9(5) . . ?
C9 C14 C15 110.0(4) . . ?
C13 C14 C15 130.1(5) . . ?
O6A C15 N1 128.4(12) . . ?
O6A C15 C14 126.6(12) . . ?
N1 C15 C14 104.7(4) . . ?
N1 C15 H15A 110.8 . . ?
C14 C15 H15A 110.8 . . ?
N1 C15 H15B 110.8 . . ?
C14 C15 H15B 110.8 . . ?
H15A C15 H15B 108.9 . . ?
O3 C16 O5 125.8(4) 10_665 . ?
O3 C16 C4 117.9(4) 10_665 9_554 ?
O5 C16 C4 116.3(4) . 9_554 ?
C6 N1 C8 124.2(3) . . ?
C6 N1 C15 124.6(3) . . ?
C8 N1 C15 111.2(4) . . ?
C1 O1 Cu1 123.6(3) 10_665 . ?
Cu1 O2 H2A 109(3) . . ?
Cu1 O2 H2B 111(3) . . ?
H2A O2 H2B 109.4(17) . . ?
C16 O3 Cu1 119.2(3) 10_665 . ?
C1 O4 Cu1 121.7(3) . . ?
C16 O5 Cu1 126.0(3) . . ?

_refine_diff_density_max         0.507
_refine_diff_density_min         -0.431
_refine_diff_density_rms         0.078

_shelxl_version_number           2014-3



####################################################################### 
# 
# 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_6
_database_code_depnum_ccdc_archive 'CCDC 1497048'
_audit_update_record             
;
2016-11-30 deposited with the CCDC.
2016-12-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C68 H42 Cl2 Cu3 N8 O18'
_chemical_formula_weight         1520.61

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

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

_cell_length_a                   13.981(2)
_cell_length_b                   13.594(2)
_cell_length_c                   30.578(5)
_cell_angle_alpha                90
_cell_angle_beta                 93.477(3)
_cell_angle_gamma                90
_cell_volume                     5801.2(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5118
_cell_measurement_theta_min      0.999
_cell_measurement_theta_max      25.0

_exptl_crystal_description       block
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.741
_exptl_crystal_F_000             3084
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    1.272
_shelx_estimated_absorpt_T_min   0.785
_shelx_estimated_absorpt_T_max   0.905
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker SMART APEX CCD'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14581
_diffrn_reflns_av_unetI/netI     0.0372
_diffrn_reflns_av_R_equivalents  0.0329
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_theta_min         1.334
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.973
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.973
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.973
_reflns_number_total             5118
_reflns_number_gt                4128
_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 SAINT'
_computing_structure_refinement  'SHELXL-2014 (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)+(0.0509P)²+7.8616P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5118
_refine_ls_number_parameters     447
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0485
_refine_ls_R_factor_gt           0.0362
_refine_ls_wR_factor_ref         0.0961
_refine_ls_wR_factor_gt          0.0908
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_restrained_S_all      1.005
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.0000 0.29389(3) 0.2500 0.02339(14) Uani 1 2 d S T P . .
Cu2 Cu 0.05036(2) 0.42433(2) 0.16922(2) 0.02516(12) Uani 1 1 d . . . . .
C1 C 0.13145(19) 0.46140(19) 0.25787(9) 0.0219(6) Uani 1 1 d . . . . .
C2 C 0.20843(19) 0.51183(19) 0.28600(9) 0.0209(6) Uani 1 1 d . . . . .
C3 C 0.22794(19) 0.6114(2) 0.28172(9) 0.0223(6) Uani 1 1 d . . . . .
H3 H 0.1925 0.6493 0.2613 0.027 Uiso 1 1 calc R U . . .
C4 C 0.30101(19) 0.65379(19) 0.30829(9) 0.0220(6) Uani 1 1 d . . . . .
C5 C 0.3197(2) 0.7629(2) 0.30394(10) 0.0250(6) Uani 1 1 d . . . . .
C6 C 0.3543(2) 0.5963(2) 0.33838(9) 0.0251(6) Uani 1 1 d . . . . .
H6 H 0.4044 0.6246 0.3554 0.030 Uiso 1 1 calc R U . . .
C7 C 0.3340(2) 0.4970(2) 0.34337(9) 0.0248(6) Uani 1 1 d . . . . .
C8 C 0.2604(2) 0.4556(2) 0.31641(10) 0.0259(6) Uani 1 1 d . . . . .
H8 H 0.2462 0.3891 0.3191 0.031 Uiso 1 1 calc R U . . .
C9 C 0.3664(2) 0.3419(2) 0.38550(11) 0.0318(7) Uani 1 1 d . . . . .
C10 C 0.4577(2) 0.4826(2) 0.40636(10) 0.0344(7) Uani 1 1 d . . . . .
H10A H 0.4326 0.5381 0.4220 0.041 Uiso 1 1 calc R U . . .
H10B H 0.5131 0.5038 0.3912 0.041 Uiso 1 1 calc R U . . .
C11 C 0.4824(2) 0.3986(2) 0.43680(10) 0.0343(7) Uani 1 1 d . . . . .
C12 C 0.5503(3) 0.3915(3) 0.47159(12) 0.0494(10) Uani 1 1 d . . . . .
H12 H 0.5881 0.4452 0.4803 0.059 Uiso 1 1 calc R U . . .
C13 C 0.5602(3) 0.3022(3) 0.49288(13) 0.0564(11) Uani 1 1 d . . . . .
H13 H 0.6060 0.2959 0.5160 0.068 Uiso 1 1 calc R U . . .
C14 C 0.5045(3) 0.2223(3) 0.48098(12) 0.0479(9) Uani 1 1 d . . . . .
H14 H 0.5128 0.1635 0.4963 0.058 Uiso 1 1 calc R U . . .
C15 C 0.4364(2) 0.2286(2) 0.44664(11) 0.0412(8) Uani 1 1 d . . . . .
H15 H 0.3981 0.1750 0.4383 0.049 Uiso 1 1 calc R U . . .
C16 C 0.4273(2) 0.3183(2) 0.42491(10) 0.0325(7) Uani 1 1 d . . . . .
C17 C 0.1482(2) 0.1866(2) 0.30790(10) 0.0287(7) Uani 1 1 d . . . . .
H17 H 0.1720 0.2476 0.3171 0.034 Uiso 1 1 calc R U . . .
C18 C 0.1908(2) 0.1021(2) 0.32560(11) 0.0335(7) Uani 1 1 d . . . . .
H18 H 0.2412 0.1068 0.3468 0.040 Uiso 1 1 calc R U . . .
C19 C 0.1585(2) 0.0119(2) 0.31169(10) 0.0334(7) Uani 1 1 d . . . . .
H19 H 0.1876 -0.0451 0.3228 0.040 Uiso 1 1 calc R U . . .
C20 C 0.0807(2) 0.0062(2) 0.28042(10) 0.0268(7) Uani 1 1 d . . . . .
C21 C 0.04054(19) 0.09455(19) 0.26539(9) 0.0221(6) Uani 1 1 d . . . . .
C22 C 0.0393(2) -0.0841(2) 0.26387(11) 0.0361(8) Uani 1 1 d . . . . .
H22 H 0.0672 -0.1436 0.2725 0.043 Uiso 1 1 calc R U . . .
C23 C -0.0535(2) 0.2826(3) 0.10565(11) 0.0402(8) Uani 1 1 d . . . . .
H23 H -0.0160 0.2324 0.1182 0.048 Uiso 1 1 calc R U . . .
C24 C -0.1203(3) 0.2594(3) 0.07153(13) 0.0531(10) Uani 1 1 d . . . . .
H24 H -0.1276 0.1947 0.0620 0.064 Uiso 1 1 calc R U . . .
C25 C -0.1748(3) 0.3320(3) 0.05229(12) 0.0537(11) Uani 1 1 d . . . . .
H25 H -0.2189 0.3172 0.0292 0.064 Uiso 1 1 calc R U . . .
C26 C -0.1646(2) 0.4289(3) 0.06717(11) 0.0411(9) Uani 1 1 d . . . . .
C27 C -0.2179(3) 0.5122(3) 0.04986(12) 0.0548(11) Uani 1 1 d . . . . .
H27 H -0.2624 0.5028 0.0264 0.066 Uiso 1 1 calc R U . . .
C28 C -0.2058(3) 0.6021(3) 0.06627(13) 0.0535(10) Uani 1 1 d . . . . .
H28 H -0.2423 0.6538 0.0544 0.064 Uiso 1 1 calc R U . . .
C29 C -0.1368(2) 0.6205(3) 0.10224(11) 0.0395(8) Uani 1 1 d . . . . .
C30 C -0.1189(3) 0.7137(3) 0.12067(13) 0.0494(10) Uani 1 1 d . . . . .
H30 H -0.1549 0.7679 0.1110 0.059 Uiso 1 1 calc R U . . .
C31 C -0.0480(3) 0.7235(3) 0.15294(12) 0.0463(9) Uani 1 1 d . . . . .
H31 H -0.0343 0.7850 0.1650 0.056 Uiso 1 1 calc R U . . .
C32 C 0.0037(3) 0.6418(2) 0.16781(11) 0.0388(8) Uani 1 1 d . . . . .
H32 H 0.0518 0.6501 0.1898 0.047 Uiso 1 1 calc R U . . .
C33 C -0.0820(2) 0.5422(2) 0.11899(10) 0.0297(7) Uani 1 1 d . . . . .
C34 C -0.0964(2) 0.4453(2) 0.10187(9) 0.0301(7) Uani 1 1 d . . . . .
Cl1 Cl 0.18420(6) 0.44766(7) 0.07361(3) 0.0452(2) Uani 1 1 d . . . . .
N1 N -0.04142(17) 0.37319(18) 0.12081(8) 0.0292(6) Uani 1 1 d . . . . .
N2 N -0.01297(18) 0.55239(18) 0.15180(8) 0.0296(6) Uani 1 1 d . . . . .
N3 N 0.07429(16) 0.18350(16) 0.27828(8) 0.0235(5) Uani 1 1 d . . . . .
N4 N 0.38422(17) 0.43992(17) 0.37579(8) 0.0290(6) Uani 1 1 d . . . . .
O1 O 0.08952(13) 0.39057(13) 0.27596(6) 0.0251(4) Uani 1 1 d . . . . .
O2 O 0.11468(14) 0.49159(13) 0.21964(6) 0.0268(5) Uani 1 1 d . . . . .
O3 O 0.40561(13) 0.79123(13) 0.31767(7) 0.0266(5) Uani 1 1 d . . . . .
O4 O 0.31215(19) 0.28669(17) 0.36567(9) 0.0549(7) Uani 1 1 d . . . . .
O5 O 0.1723(2) 0.4523(3) 0.11932(9) 0.0803(10) Uani 1 1 d . . . . .
O6 O 0.0959(2) 0.4754(2) 0.05104(10) 0.0783(9) Uani 1 1 d . . . . .
O7 O 0.2564(3) 0.5163(3) 0.06360(12) 0.1045(13) Uani 1 1 d . . . . .
O8 O 0.2063(3) 0.3545(3) 0.05989(15) 0.1236(17) Uani 1 1 d . . . . .
O9 O 0.25673(15) 0.81541(15) 0.28800(8) 0.0416(6) 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
Cu1 O1 1.9503(18) . ?
Cu1 O1 1.9503(18) 2 ?
Cu1 N3 1.992(2) 2 ?
Cu1 N3 1.992(2) . ?
Cu2 O3 1.9451(18) 4_545 ?
Cu2 O2 1.9629(19) . ?
Cu2 N2 2.010(2) . ?
Cu2 N1 2.023(2) . ?
Cu2 O5 2.386(3) . ?
C1 O2 1.248(3) . ?
C1 O1 1.271(3) . ?
C1 C2 1.502(4) . ?
C2 C8 1.376(4) . ?
C2 C3 1.388(4) . ?
C3 C4 1.391(4) . ?
C4 C6 1.389(4) . ?
C4 C5 1.514(4) . ?
C5 O9 1.212(3) . ?
C5 O3 1.306(3) . ?
C6 C7 1.389(4) . ?
C7 C8 1.397(4) . ?
C7 N4 1.412(3) . ?
C9 O4 1.204(4) . ?
C9 N4 1.391(4) . ?
C9 C16 1.468(4) . ?
C10 N4 1.467(4) . ?
C10 C11 1.501(4) . ?
C11 C16 1.372(4) . ?
C11 C12 1.386(4) . ?
C12 C13 1.381(5) . ?
C13 C14 1.372(5) . ?
C14 C15 1.376(5) . ?
C15 C16 1.392(4) . ?
C17 N3 1.332(3) . ?
C17 C18 1.390(4) . ?
C18 C19 1.365(4) . ?
C19 C20 1.406(4) . ?
C20 C21 1.393(4) . ?
C20 C22 1.435(4) . ?
C21 N3 1.348(3) . ?
C21 C21 1.429(5) 2 ?
C22 C22 1.347(6) 2 ?
C23 N1 1.323(4) . ?
C23 C24 1.393(5) . ?
C24 C25 1.359(5) . ?
C25 C26 1.398(5) . ?
C26 C34 1.401(4) . ?
C26 C27 1.438(5) . ?
C27 C28 1.328(6) . ?
C28 C29 1.440(5) . ?
C29 C33 1.391(4) . ?
C29 C30 1.403(5) . ?
C30 C31 1.362(5) . ?
C31 C32 1.386(5) . ?
C32 N2 1.326(4) . ?
C33 N2 1.357(4) . ?
C33 C34 1.426(4) . ?
C34 N1 1.355(4) . ?
Cl1 O8 1.375(3) . ?
Cl1 O7 1.421(3) . ?
Cl1 O5 1.419(3) . ?
Cl1 O6 1.428(3) . ?
O3 Cu2 1.9452(18) 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
O1 Cu1 O1 95.26(11) . 2 ?
O1 Cu1 N3 171.51(9) . 2 ?
O1 Cu1 N3 91.50(8) 2 2 ?
O1 Cu1 N3 91.50(8) . . ?
O1 Cu1 N3 171.51(9) 2 . ?
N3 Cu1 N3 82.27(13) 2 . ?
O3 Cu2 O2 98.47(8) 4_545 . ?
O3 Cu2 N2 171.47(9) 4_545 . ?
O2 Cu2 N2 88.75(9) . . ?
O3 Cu2 N1 90.56(9) 4_545 . ?
O2 Cu2 N1 167.16(9) . . ?
N2 Cu2 N1 81.60(10) . . ?
O3 Cu2 O5 92.89(11) 4_545 . ?
O2 Cu2 O5 96.72(9) . . ?
N2 Cu2 O5 90.74(12) . . ?
N1 Cu2 O5 91.88(10) . . ?
O2 C1 O1 126.3(2) . . ?
O2 C1 C2 118.3(2) . . ?
O1 C1 C2 115.4(2) . . ?
C8 C2 C3 120.4(2) . . ?
C8 C2 C1 117.6(2) . . ?
C3 C2 C1 121.9(2) . . ?
C2 C3 C4 119.4(2) . . ?
C6 C4 C3 119.9(2) . . ?
C6 C4 C5 121.4(2) . . ?
C3 C4 C5 118.7(2) . . ?
O9 C5 O3 126.0(3) . . ?
O9 C5 C4 119.1(2) . . ?
O3 C5 C4 114.9(2) . . ?
C4 C6 C7 120.9(2) . . ?
C6 C7 C8 118.3(2) . . ?
C6 C7 N4 121.0(2) . . ?
C8 C7 N4 120.7(2) . . ?
C2 C8 C7 121.0(3) . . ?
O4 C9 N4 127.2(3) . . ?
O4 C9 C16 126.4(3) . . ?
N4 C9 C16 106.4(2) . . ?
N4 C10 C11 102.7(2) . . ?
C16 C11 C12 119.7(3) . . ?
C16 C11 C10 109.7(3) . . ?
C12 C11 C10 130.5(3) . . ?
C13 C12 C11 117.8(3) . . ?
C14 C13 C12 122.2(3) . . ?
C13 C14 C15 120.6(3) . . ?
C14 C15 C16 117.2(3) . . ?
C11 C16 C15 122.5(3) . . ?
C11 C16 C9 109.4(3) . . ?
C15 C16 C9 127.9(3) . . ?
N3 C17 C18 122.4(3) . . ?
C19 C18 C17 119.7(3) . . ?
C18 C19 C20 119.4(3) . . ?
C21 C20 C19 117.1(3) . . ?
C21 C20 C22 118.3(3) . . ?
C19 C20 C22 124.5(3) . . ?
N3 C21 C20 123.4(3) . . ?
N3 C21 C21 116.25(15) . 2 ?
C20 C21 C21 120.37(16) . 2 ?
C22 C22 C20 121.23(17) 2 . ?
N1 C23 C24 122.6(3) . . ?
C25 C24 C23 119.5(4) . . ?
C24 C25 C26 120.0(3) . . ?
C34 C26 C25 116.6(3) . . ?
C34 C26 C27 117.8(3) . . ?
C25 C26 C27 125.6(3) . . ?
C28 C27 C26 122.3(3) . . ?
C27 C28 C29 120.8(3) . . ?
C33 C29 C30 117.6(3) . . ?
C33 C29 C28 118.5(3) . . ?
C30 C29 C28 123.9(3) . . ?
C31 C30 C29 118.8(3) . . ?
C30 C31 C32 120.1(3) . . ?
N2 C32 C31 122.5(3) . . ?
N2 C33 C29 123.0(3) . . ?
N2 C33 C34 116.4(3) . . ?
C29 C33 C34 120.6(3) . . ?
N1 C34 C26 123.4(3) . . ?
N1 C34 C33 116.6(3) . . ?
C26 C34 C33 120.0(3) . . ?
O8 Cl1 O7 111.3(3) . . ?
O8 Cl1 O5 112.5(3) . . ?
O7 Cl1 O5 108.10(19) . . ?
O8 Cl1 O6 107.4(2) . . ?
O7 Cl1 O6 109.1(2) . . ?
O5 Cl1 O6 108.3(2) . . ?
C23 N1 C34 117.8(3) . . ?
C23 N1 Cu2 129.7(2) . . ?
C34 N1 Cu2 112.5(2) . . ?
C32 N2 C33 117.9(3) . . ?
C32 N2 Cu2 129.2(2) . . ?
C33 N2 Cu2 112.9(2) . . ?
C17 N3 C21 118.1(2) . . ?
C17 N3 Cu1 129.29(19) . . ?
C21 N3 Cu1 112.62(17) . . ?
C9 N4 C7 126.1(2) . . ?
C9 N4 C10 111.8(2) . . ?
C7 N4 C10 122.0(2) . . ?
C1 O1 Cu1 129.40(18) . . ?
C1 O2 Cu2 129.33(17) . . ?
C5 O3 Cu2 127.84(17) . 4 ?
Cl1 O5 Cu2 138.95(17) . . ?

_refine_diff_density_max         0.585
_refine_diff_density_min         -0.377
_refine_diff_density_rms         0.066

_shelxl_version_number           2014-3

####################################################################### 
# 
# 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_7
_database_code_depnum_ccdc_archive 'CCDC 1497049'
_audit_update_record             
;
2016-11-30 deposited with the CCDC.
2016-12-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C35 H34 Co N6 O6'
_chemical_formula_weight         693.61

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Co Co 0.3494 0.9721 '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           13
_space_group_name_H-M_alt        'P 2/c'
_space_group_name_Hall           '-P 2yc'

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

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

_cell_length_a                   11.807(9)
_cell_length_b                   9.928(9)
_cell_length_c                   23.44(2)
_cell_angle_alpha                90
_cell_angle_beta                 97.668(15)
_cell_angle_gamma                90
_cell_volume                     2723(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4780
_cell_measurement_theta_min      0.996
_cell_measurement_theta_max      24.995

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.692
_exptl_crystal_F_000             1444
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.697
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker SMART APEX CCD'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12303
_diffrn_reflns_av_unetI/netI     0.0574
_diffrn_reflns_av_R_equivalents  0.0452
_diffrn_reflns_limit_h_min       ?
_diffrn_reflns_limit_h_max       ?
_diffrn_reflns_limit_k_min       ?
_diffrn_reflns_limit_k_max       ?
_diffrn_reflns_limit_l_min       ?
_diffrn_reflns_limit_l_max       ?
_diffrn_reflns_theta_min         1.740
_diffrn_reflns_theta_max         24.995
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.969
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.969
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.969
_reflns_number_total             4780
_reflns_number_gt                3162
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Data were apparently pre-merged, so _diffrn_reflns_number
 etc. will have to be added later.
 
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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 SAINT'
_computing_structure_refinement  'SHELXL-2014 (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)+(0.0537P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4780
_refine_ls_number_parameters     376
_refine_ls_number_restraints     19
_refine_ls_R_factor_all          0.0783
_refine_ls_R_factor_gt           0.0465
_refine_ls_wR_factor_ref         0.1158
_refine_ls_wR_factor_gt          0.1042
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_restrained_S_all      1.075
_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
Co1 Co 0.55914(3) 0.21225(5) 0.35856(2) 0.03774(16) Uani 1 1 d . U . . .
C1 C 0.5102(3) 0.4834(3) 0.33891(14) 0.0470(9) Uani 1 1 d . . . . .
C2 C 0.4473(2) 0.6063(3) 0.31467(12) 0.0361(7) Uani 1 1 d . . . . .
C3 C 0.4889(3) 0.7323(3) 0.33012(12) 0.0361(7) Uani 1 1 d . . . . .
H3 H 0.5565 0.7412 0.3552 0.043 Uiso 1 1 calc R U . . .
C4 C 0.4305(2) 0.8454(3) 0.30854(12) 0.0334(7) Uani 1 1 d . . . . .
C5 C 0.4759(3) 0.9823(3) 0.32515(12) 0.0402(8) Uani 1 1 d . . . . .
C6 C 0.3297(3) 0.8330(3) 0.27084(12) 0.0387(8) Uani 1 1 d . . . . .
H6 H 0.2905 0.9097 0.2565 0.046 Uiso 1 1 calc R U . . .
C7 C 0.3465(3) 0.5944(3) 0.27686(12) 0.0406(8) Uani 1 1 d . . . . .
H7 H 0.3185 0.5092 0.2664 0.049 Uiso 1 1 calc R U . . .
C8 C 0.2874(2) 0.7065(3) 0.25464(12) 0.0379(7) Uani 1 1 d . . . . .
C9 C 0.1407(3) 0.5526(4) 0.20141(14) 0.0600(10) Uani 1 1 d . . . . .
H9A H 0.1888 0.5081 0.1767 0.072 Uiso 1 1 calc R U . . .
H9B H 0.1359 0.4973 0.2351 0.072 Uiso 1 1 calc R U . . .
C10 C 0.1068(3) 0.7873(5) 0.19752(14) 0.0534(9) Uani 1 1 d . . . . .
C11 C 0.0059(3) 0.7181(5) 0.16790(14) 0.0585(10) Uani 1 1 d . . . . .
C12 C 0.0249(3) 0.5827(5) 0.16994(14) 0.0674(12) Uani 1 1 d . . . . .
C13 C -0.0597(4) 0.4911(6) 0.14658(17) 0.0892(16) Uani 1 1 d . . . . .
H13 H -0.0474 0.3985 0.1475 0.107 Uiso 1 1 calc R U . . .
C16 C -0.0982(3) 0.7717(5) 0.14239(15) 0.0806(15) Uani 1 1 d . . . . .
H16 H -0.1108 0.8642 0.1406 0.097 Uiso 1 1 calc R U . . .
C19 C -0.0482(3) 0.2480(4) 0.45562(15) 0.0595(11) Uani 1 1 d D . . . .
C20 C -0.0776(3) 0.1617(4) 0.40892(16) 0.0626(11) Uani 1 1 d . . . . .
H20 H -0.0215 0.1124 0.3939 0.075 Uiso 1 1 calc R U . . .
C21 C -0.1898(3) 0.1503(4) 0.38547(14) 0.0512(9) Uani 1 1 d . . . . .
H21 H -0.2080 0.0909 0.3550 0.061 Uiso 1 1 calc R U . . .
C22 C 0.0758(3) 0.2775(6) 0.4825(2) 0.0641(17) Uani 0.844(8) 1 d . . P A 1
H22A H 0.1260 0.2743 0.4530 0.077 Uiso 0.844(8) 1 calc R U P A 1
H22B H 0.0805 0.3668 0.4994 0.077 Uiso 0.844(8) 1 calc R U P A 1
C23 C 0.1124(3) 0.1735(5) 0.52822(17) 0.0490(15) Uani 0.844(8) 1 d . . P A 1
H23A H 0.1130 0.0850 0.5108 0.059 Uiso 0.844(8) 1 calc R U P A 1
H23B H 0.0587 0.1720 0.5561 0.059 Uiso 0.844(8) 1 calc R U P A 1
C22A C 0.0670(12) 0.190(2) 0.4807(9) 0.041(7) Uani 0.156(8) 1 d D U P A 2
H22C H 0.0565 0.0987 0.4937 0.049 Uiso 0.156(8) 1 calc R U P A 2
H22D H 0.1165 0.1865 0.4509 0.049 Uiso 0.156(8) 1 calc R U P A 2
C23A C 0.1234(12) 0.2724(19) 0.5301(7) 0.038(6) Uani 0.156(8) 1 d D U P A 2
H23C H 0.0710 0.2827 0.5584 0.046 Uiso 0.156(8) 1 calc R U P A 2
H23D H 0.1400 0.3614 0.5164 0.046 Uiso 0.156(8) 1 calc R U P A 2
C24 C 0.2339(2) 0.2084(4) 0.55886(13) 0.0587(11) Uani 1 1 d D . . . .
H24A H 0.2326 0.2966 0.5765 0.070 Uiso 0.844(8) 1 calc R U P A 1
H24B H 0.2561 0.1432 0.5891 0.070 Uiso 0.844(8) 1 calc R U P A 1
H24C H 0.2633 0.2590 0.5930 0.070 Uiso 0.156(8) 1 calc R U P A 2
H24D H 0.2192 0.1169 0.5704 0.070 Uiso 0.156(8) 1 calc R U P A 2
C25 C 0.3204(3) 0.2078(4) 0.51723(12) 0.0469(9) Uani 1 1 d . . . . .
C26 C 0.3490(3) 0.0910(4) 0.49068(14) 0.0592(10) Uani 1 1 d . . . . .
H26 H 0.3189 0.0090 0.5005 0.071 Uiso 1 1 calc R U . . .
C27 C 0.4221(3) 0.0955(4) 0.44961(13) 0.0523(9) Uani 1 1 d . . . . .
H27 H 0.4399 0.0150 0.4326 0.063 Uiso 1 1 calc R U . . .
C28 C 0.3709(3) 0.3226(4) 0.50126(14) 0.0559(10) Uani 1 1 d . . . . .
H28 H 0.3568 0.4039 0.5187 0.067 Uiso 1 1 calc R U . . .
C29 C 0.4431(3) 0.3195(4) 0.45926(14) 0.0530(10) Uani 1 1 d . . . . .
H29 H 0.4752 0.4001 0.4491 0.064 Uiso 1 1 calc R U . . .
C14A C -0.1629(4) 0.5468(8) 0.1220(2) 0.107(2) Uani 1 1 d . . . . .
H14A H -0.2215 0.4898 0.1064 0.128 Uiso 1 1 calc R U . . .
C15A C -0.1807(4) 0.6824(8) 0.12011(19) 0.104(2) Uani 1 1 d . . . . .
H15A H -0.2510 0.7153 0.1032 0.125 Uiso 1 1 calc R U . . .
C17A C -0.2451(3) 0.3000(4) 0.44897(13) 0.0508(9) Uani 1 1 d . . . . .
H17A H -0.3026 0.3478 0.4636 0.061 Uiso 1 1 calc R U . . .
C18A C -0.1353(3) 0.3159(4) 0.47493(15) 0.0600(11) Uani 1 1 d . . . . .
H18A H -0.1200 0.3740 0.5062 0.072 Uiso 1 1 calc R U . . .
N1 N 0.1830(2) 0.6881(3) 0.21746(11) 0.0465(7) Uani 1 1 d . . . . .
N2 N 0.4687(2) 0.2081(3) 0.43283(10) 0.0442(7) Uani 1 1 d . . . . .
N3 N -0.2742(2) 0.2198(3) 0.40401(10) 0.0393(6) Uani 1 1 d . . . . .
O1 O 0.6447(2) 0.2331(3) 0.28148(9) 0.0530(6) Uani 1 1 d D . . . .
H1A H 0.6407 0.1616 0.2638 0.079 Uiso 1 1 calc DR U . . .
O2 O 0.4670(2) 0.3703(2) 0.32257(10) 0.0586(7) Uani 1 1 d . . . . .
O3 O 0.5971(2) 0.4947(3) 0.37315(10) 0.0696(8) Uani 1 1 d . . . . .
O5 O 0.57366(19) 0.9953(2) 0.35214(9) 0.0525(6) Uani 1 1 d . . . . .
O6 O 0.1197(2) 0.9087(3) 0.20299(11) 0.0718(8) Uani 1 1 d . . . . .
H1B H 0.605(4) 0.291(3) 0.2614(17) 0.16(3) Uiso 1 1 d D . . . .
O4 O 0.4138(2) 0.0835(2) 0.31295(9) 0.0513(6) Uani 1 1 d . U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Co1 O2 2.028(3) . ?
Co1 N3 2.110(3) 1_655 ?
Co1 N2 2.161(3) . ?
Co1 O5 2.168(3) 1_545 ?
Co1 O1 2.194(3) . ?
Co1 O4 2.287(2) . ?
C1 O3 1.220(4) . ?
C1 O2 1.271(4) . ?
C1 C2 1.500(4) . ?
C2 C7 1.391(4) . ?
C2 C3 1.375(4) . ?
C3 C4 1.378(4) . ?
C3 H3 0.9300 . ?
C4 C6 1.390(4) . ?
C4 C5 1.493(4) . ?
C5 O4 1.254(4) 1_565 ?
C5 O5 1.247(4) . ?
C6 C8 1.386(4) . ?
C6 H6 0.9300 . ?
C7 C8 1.378(4) . ?
C7 H7 0.9300 . ?
C8 N1 1.424(4) . ?
C9 C12 1.495(5) . ?
C9 N1 1.466(4) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 O6 1.220(5) . ?
C10 N1 1.372(5) . ?
C10 C11 1.468(5) . ?
C11 C16 1.398(5) . ?
C11 C12 1.363(6) . ?
C12 C13 1.407(5) . ?
C13 C14A 1.391(7) . ?
C13 H13 0.9300 . ?
C16 C15A 1.368(7) . ?
C16 H16 0.9300 . ?
C19 C18A 1.357(5) . ?
C19 C20 1.397(5) . ?
C19 C22A 1.521(10) . ?
C19 C22 1.543(5) . ?
C20 C21 1.369(4) . ?
C20 H20 0.9300 . ?
C21 N3 1.332(4) . ?
C21 H21 0.9300 . ?
C22 C23 1.508(6) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C23 C24 1.555(5) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C22A C23A 1.500(10) . ?
C22A H22C 0.9700 . ?
C22A H22D 0.9700 . ?
C23A C24 1.525(10) . ?
C23A H23C 0.9700 . ?
C23A H23D 0.9700 . ?
C24 C25 1.503(5) . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C24 H24C 0.9700 . ?
C24 H24D 0.9700 . ?
C25 C26 1.379(5) . ?
C25 C28 1.362(5) . ?
C26 C27 1.376(5) . ?
C26 H26 0.9300 . ?
C27 N2 1.329(4) . ?
C27 H27 0.9300 . ?
C28 C29 1.386(5) . ?
C28 H28 0.9300 . ?
C29 N2 1.322(4) . ?
C29 H29 0.9300 . ?
C14A C15A 1.362(8) . ?
C14A H14A 0.9300 . ?
C15A H15A 0.9300 . ?
C17A N3 1.328(4) . ?
C17A C18A 1.366(4) . ?
C17A H17A 0.9300 . ?
C18A H18A 0.9300 . ?
N3 Co1 2.110(3) 1_455 ?
O1 H1A 0.8200 . ?
O1 H1B 0.845(10) . ?
O5 Co1 2.168(3) 1_565 ?
O4 C5 1.254(4) 1_545 ?

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 Co1 N3 126.51(11) . 1_655 ?
O2 Co1 N2 93.11(11) . . ?
N3 Co1 N2 96.99(11) 1_655 . ?
O2 Co1 O5 141.53(9) . 1_545 ?
N3 Co1 O5 89.63(9) 1_655 1_545 ?
N2 Co1 O5 95.13(10) . 1_545 ?
O2 Co1 O1 82.23(11) . . ?
N3 Co1 O1 84.94(11) 1_655 . ?
N2 Co1 O1 175.20(11) . . ?
O5 Co1 O1 89.28(9) 1_545 . ?
O2 Co1 O4 84.86(11) . . ?
N3 Co1 O4 147.86(10) 1_655 . ?
N2 Co1 O4 86.88(10) . . ?
O5 Co1 O4 58.23(8) 1_545 . ?
O1 Co1 O4 93.83(10) . . ?
O3 C1 O2 123.2(3) . . ?
O3 C1 C2 120.3(3) . . ?
O2 C1 C2 116.5(3) . . ?
C7 C2 C3 119.3(3) . . ?
C7 C2 C1 120.7(3) . . ?
C3 C2 C1 120.0(3) . . ?
C2 C3 C4 120.1(3) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 H3 119.9 . . ?
C6 C4 C3 120.3(3) . . ?
C6 C4 C5 119.6(3) . . ?
C3 C4 C5 120.1(3) . . ?
O4 C5 O5 120.4(3) 1_565 . ?
O4 C5 C4 119.4(3) 1_565 . ?
O5 C5 C4 120.1(3) . . ?
C8 C6 C4 120.1(3) . . ?
C8 C6 H6 120.0 . . ?
C4 C6 H6 120.0 . . ?
C2 C7 C8 121.3(3) . . ?
C2 C7 H7 119.3 . . ?
C8 C7 H7 119.3 . . ?
C6 C8 N1 122.3(3) . . ?
C6 C8 C7 118.9(3) . . ?
N1 C8 C7 118.8(3) . . ?
C12 C9 N1 101.6(3) . . ?
C12 C9 H9A 111.5 . . ?
N1 C9 H9A 111.5 . . ?
C12 C9 H9B 111.5 . . ?
N1 C9 H9B 111.5 . . ?
H9A C9 H9B 109.3 . . ?
O6 C10 N1 127.3(3) . . ?
O6 C10 C11 126.5(4) . . ?
N1 C10 C11 106.2(4) . . ?
C16 C11 C12 121.5(4) . . ?
C16 C11 C10 129.5(5) . . ?
C12 C11 C10 109.0(4) . . ?
C13 C12 C11 121.3(4) . . ?
C13 C12 C9 128.2(5) . . ?
C11 C12 C9 110.5(3) . . ?
C12 C13 C14A 116.2(5) . . ?
C12 C13 H13 121.9 . . ?
C14A C13 H13 121.9 . . ?
C11 C16 C15A 117.2(5) . . ?
C11 C16 H16 121.4 . . ?
C15A C16 H16 121.4 . . ?
C18A C19 C20 116.5(3) . . ?
C18A C19 C22A 137.5(8) . . ?
C20 C19 C22A 100.8(7) . . ?
C18A C19 C22 119.3(4) . . ?
C20 C19 C22 124.0(4) . . ?
C19 C20 C21 119.4(3) . . ?
C19 C20 H20 120.3 . . ?
C21 C20 H20 120.3 . . ?
N3 C21 C20 123.5(3) . . ?
N3 C21 H21 118.2 . . ?
C20 C21 H21 118.2 . . ?
C23 C22 C19 109.1(4) . . ?
C23 C22 H22A 109.9 . . ?
C19 C22 H22A 109.9 . . ?
C23 C22 H22B 109.9 . . ?
C19 C22 H22B 109.9 . . ?
H22A C22 H22B 108.3 . . ?
C22 C23 C24 109.6(4) . . ?
C22 C23 H23A 109.8 . . ?
C24 C23 H23A 109.8 . . ?
C22 C23 H23B 109.8 . . ?
C24 C23 H23B 109.8 . . ?
H23A C23 H23B 108.2 . . ?
C23A C22A C19 112.0(10) . . ?
C23A C22A H22C 109.2 . . ?
C19 C22A H22C 109.2 . . ?
C23A C22A H22D 109.2 . . ?
C19 C22A H22D 109.2 . . ?
H22C C22A H22D 107.9 . . ?
C22A C23A C24 112.3(10) . . ?
C22A C23A H23C 109.1 . . ?
C24 C23A H23C 109.1 . . ?
C22A C23A H23D 109.1 . . ?
C24 C23A H23D 109.1 . . ?
H23C C23A H23D 107.9 . . ?
C25 C24 C23A 109.3(8) . . ?
C25 C24 C23 111.3(3) . . ?
C25 C24 H24A 109.4 . . ?
C23 C24 H24A 109.4 . . ?
C25 C24 H24B 109.4 . . ?
C23 C24 H24B 109.4 . . ?
H24A C24 H24B 108.0 . . ?
C25 C24 H24C 109.8 . . ?
C23A C24 H24C 109.8 . . ?
C25 C24 H24D 109.8 . . ?
C23A C24 H24D 109.8 . . ?
H24C C24 H24D 108.3 . . ?
C26 C25 C28 115.9(3) . . ?
C26 C25 C24 121.7(4) . . ?
C28 C25 C24 122.4(4) . . ?
C25 C26 C27 120.2(4) . . ?
C25 C26 H26 119.9 . . ?
C27 C26 H26 119.9 . . ?
N2 C27 C26 123.9(4) . . ?
N2 C27 H27 118.1 . . ?
C26 C27 H27 118.1 . . ?
C29 C28 C25 120.7(4) . . ?
C29 C28 H28 119.7 . . ?
C25 C28 H28 119.7 . . ?
N2 C29 C28 123.5(3) . . ?
N2 C29 H29 118.2 . . ?
C28 C29 H29 118.2 . . ?
C15A C14A C13 122.0(5) . . ?
C15A C14A H14A 119.0 . . ?
C13 C14A H14A 119.0 . . ?
C14A C15A C16 121.9(5) . . ?
C14A C15A H15A 119.0 . . ?
C16 C15A H15A 119.0 . . ?
N3 C17A C18A 123.5(3) . . ?
N3 C17A H17A 118.2 . . ?
C18A C17A H17A 118.2 . . ?
C19 C18A C17A 120.7(3) . . ?
C19 C18A H18A 119.7 . . ?
C17A C18A H18A 119.7 . . ?
C10 N1 C8 126.3(3) . . ?
C10 N1 C9 112.7(3) . . ?
C8 N1 C9 120.8(3) . . ?
C27 N2 C29 115.8(3) . . ?
C27 N2 Co1 121.5(2) . . ?
C29 N2 Co1 122.0(3) . . ?
C21 N3 C17A 116.3(3) . . ?
C21 N3 Co1 120.3(2) . 1_455 ?
C17A N3 Co1 123.2(2) . 1_455 ?
Co1 O1 H1A 109.5 . . ?
Co1 O1 H1B 104(4) . . ?
H1A O1 H1B 108.5 . . ?
C1 O2 Co1 112.7(2) . . ?
C5 O5 Co1 93.52(19) . 1_565 ?
C5 O4 Co1 87.8(2) 1_545 . ?

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
O3 C1 C2 C7 -178.2(3) . . . . ?
O2 C1 C2 C7 0.7(4) . . . . ?
O3 C1 C2 C3 1.3(5) . . . . ?
O2 C1 C2 C3 -179.8(3) . . . . ?
C7 C2 C3 C4 0.4(4) . . . . ?
C1 C2 C3 C4 -179.1(3) . . . . ?
C2 C3 C4 C6 -0.3(4) . . . . ?
C2 C3 C4 C5 -179.8(3) . . . . ?
C6 C4 C5 O4 11.9(4) . . . 1_565 ?
C3 C4 C5 O4 -168.6(3) . . . 1_565 ?
C6 C4 C5 O5 -169.8(3) . . . . ?
C3 C4 C5 O5 9.7(4) . . . . ?
C3 C4 C6 C8 -0.2(4) . . . . ?
C5 C4 C6 C8 179.3(3) . . . . ?
C3 C2 C7 C8 -0.1(4) . . . . ?
C1 C2 C7 C8 179.5(3) . . . . ?
C4 C6 C8 N1 178.2(3) . . . . ?
C4 C6 C8 C7 0.5(4) . . . . ?
C2 C7 C8 C6 -0.4(4) . . . . ?
C2 C7 C8 N1 -178.2(2) . . . . ?
O6 C10 C11 C16 -3.6(6) . . . . ?
N1 C10 C11 C16 176.5(3) . . . . ?
O6 C10 C11 C12 178.7(4) . . . . ?
N1 C10 C11 C12 -1.1(4) . . . . ?
C16 C11 C12 C13 -0.2(6) . . . . ?
C10 C11 C12 C13 177.7(3) . . . . ?
C16 C11 C12 C9 -177.8(3) . . . . ?
C10 C11 C12 C9 0.1(4) . . . . ?
N1 C9 C12 C13 -176.4(4) . . . . ?
N1 C9 C12 C11 0.9(4) . . . . ?
C11 C12 C13 C14A -0.5(6) . . . . ?
C9 C12 C13 C14A 176.7(4) . . . . ?
C12 C11 C16 C15A 0.7(5) . . . . ?
C10 C11 C16 C15A -176.7(4) . . . . ?
C18A C19 C20 C21 0.1(6) . . . . ?
C22A C19 C20 C21 159.1(11) . . . . ?
C22 C19 C20 C21 -175.1(4) . . . . ?
C19 C20 C21 N3 1.4(6) . . . . ?
C18A C19 C22 C23 97.0(6) . . . . ?
C20 C19 C22 C23 -87.9(6) . . . . ?
C22A C19 C22 C23 -36.4(16) . . . . ?
C19 C22 C23 C24 -175.7(3) . . . . ?
C18A C19 C22A C23A -33(3) . . . . ?
C20 C19 C22A C23A 175.7(18) . . . . ?
C22 C19 C22A C23A 37.0(12) . . . . ?
C19 C22A C23A C24 175.0(13) . . . . ?
C22A C23A C24 C25 66(2) . . . . ?
C22A C23A C24 C23 -34.5(14) . . . . ?
C22 C23 C24 C25 -61.0(5) . . . . ?
C22 C23 C24 C23A 33.2(12) . . . . ?
C23A C24 C25 C26 -106.3(8) . . . . ?
C23 C24 C25 C26 -66.2(4) . . . . ?
C23A C24 C25 C28 70.5(8) . . . . ?
C23 C24 C25 C28 110.5(4) . . . . ?
C28 C25 C26 C27 -1.7(5) . . . . ?
C24 C25 C26 C27 175.2(3) . . . . ?
C25 C26 C27 N2 -0.2(5) . . . . ?
C26 C25 C28 C29 2.2(5) . . . . ?
C24 C25 C28 C29 -174.7(3) . . . . ?
C25 C28 C29 N2 -0.9(5) . . . . ?
C12 C13 C14A C15A 0.6(7) . . . . ?
C13 C14A C15A C16 -0.1(8) . . . . ?
C11 C16 C15A C14A -0.5(7) . . . . ?
C20 C19 C18A C17A -0.6(6) . . . . ?
C22A C19 C18A C17A -149.1(14) . . . . ?
C22 C19 C18A C17A 174.8(4) . . . . ?
N3 C17A C18A C19 -0.4(6) . . . . ?
O6 C10 N1 C8 8.1(6) . . . . ?
C11 C10 N1 C8 -172.1(3) . . . . ?
O6 C10 N1 C9 -178.0(4) . . . . ?
C11 C10 N1 C9 1.8(4) . . . . ?
C6 C8 N1 C10 -6.4(4) . . . . ?
C7 C8 N1 C10 171.3(3) . . . . ?
C6 C8 N1 C9 -179.8(3) . . . . ?
C7 C8 N1 C9 -2.1(4) . . . . ?
C12 C9 N1 C10 -1.7(4) . . . . ?
C12 C9 N1 C8 172.6(2) . . . . ?
C26 C27 N2 C29 1.6(4) . . . . ?
C26 C27 N2 Co1 -169.5(2) . . . . ?
C28 C29 N2 C27 -1.1(5) . . . . ?
C28 C29 N2 Co1 170.0(2) . . . . ?
C20 C21 N3 C17A -2.3(5) . . . . ?
C20 C21 N3 Co1 172.6(3) . . . 1_455 ?
C18A C17A N3 C21 1.8(5) . . . . ?
C18A C17A N3 Co1 -173.0(3) . . . 1_455 ?
O3 C1 O2 Co1 -0.8(4) . . . . ?
C2 C1 O2 Co1 -179.71(19) . . . . ?
O4 C5 O5 Co1 0.3(3) 1_565 . . 1_565 ?
C4 C5 O5 Co1 -177.9(2) . . . 1_565 ?

_refine_diff_density_max         0.716
_refine_diff_density_min         -0.282
_refine_diff_density_rms         0.059

_shelxl_version_number           2014-3



####################################################################### 
# 
# 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_8
_database_code_depnum_ccdc_archive 'CCDC 1497050'
_audit_update_record             
;
2016-11-30 deposited with the CCDC.
2016-12-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C32 H36 Co N4 O11'
_chemical_formula_weight         711.58

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'
Co Co 0.3494 0.9721 '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                   14.579(4)
_cell_length_b                   16.227(4)
_cell_length_c                   15.737(3)
_cell_angle_alpha                90
_cell_angle_beta                 117.599(18)
_cell_angle_gamma                90
_cell_volume                     3299.3(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    5810
_cell_measurement_theta_min      0.999
_cell_measurement_theta_max      24.999

_exptl_crystal_description       Block
_exptl_crystal_colour            purple
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.433
_exptl_crystal_F_000             1484
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_absorpt_coefficient_mu    0.586
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker SMART APEX CCD'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16679
_diffrn_reflns_av_unetI/netI     0.0452
_diffrn_reflns_av_R_equivalents  0.0388
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.576
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.973
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.973
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.973
_reflns_number_total             5810
_reflns_number_gt                4395
_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 (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)+(0.0495P)²+0.6316P] 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         5810
_refine_ls_number_parameters     470
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.0602
_refine_ls_R_factor_gt           0.0409
_refine_ls_wR_factor_ref         0.1056
_refine_ls_wR_factor_gt          0.0974
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_restrained_S_all      1.059
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C5 C 0.2289(2) 0.35945(16) 0.61647(19) 0.0334(6) Uani 1 1 d . U . . .
O8 O 0.0907(2) 0.3198(2) 0.1261(2) 0.0763(8) Uani 1 1 d . . . . .
O10 O 0.1027(2) 0.5989(2) 0.9350(2) 0.0690(7) Uani 1 1 d . . . . .
O9 O 0.13032(19) 0.44589(17) 0.0225(2) 0.0624(7) Uani 1 1 d . . . . .
Co1 Co 0.26238(3) 0.01243(2) 0.27022(2) 0.02948(12) Uani 1 1 d . U . . .
O7 O 0.10143(13) 0.04606(12) 0.20614(14) 0.0373(4) Uani 1 1 d . U . . .
H7WB H 0.0910 0.0751 0.2435 0.056 Uiso 1 1 calc R U . . .
O3 O 0.27636(13) 0.42113(11) 0.66604(13) 0.0403(5) Uani 1 1 d . U . . .
O6 O 0.24375(16) -0.05977(13) 0.37166(15) 0.0443(5) Uani 1 1 d . U . . .
H6WB H 0.1822 -0.0622 0.3576 0.066 Uiso 1 1 calc R U . . .
O1 O 0.30768(13) 0.11132(11) 0.36330(13) 0.0388(4) Uani 1 1 d . U . . .
O5 O 0.62530(13) 0.19023(11) 0.57032(13) 0.0394(5) Uani 1 1 d . U . . .
N2 N 0.41881(16) -0.02509(12) 0.31301(15) 0.0328(5) Uani 1 1 d . U . . .
O2 O 0.16098(13) 0.12355(11) 0.37435(13) 0.0427(5) Uani 1 1 d . . . . .
O4 O 0.13746(14) 0.34011(12) 0.59431(15) 0.0477(5) Uani 1 1 d . U . . .
N1 N 0.24220(16) -0.09569(12) 0.18398(15) 0.0342(5) Uani 1 1 d . U . . .
N3 N 0.56584(15) 0.29267(13) 0.63541(15) 0.0342(5) Uani 1 1 d . U . . .
C2 C 0.30386(18) 0.20549(15) 0.47683(18) 0.0303(6) Uani 1 1 d . U . . .
C1 C 0.25331(19) 0.14246(15) 0.39867(18) 0.0315(6) Uani 1 1 d . U . . .
C27 C 0.42643(19) -0.08447(15) 0.25619(18) 0.0317(6) Uani 1 1 d . . . . .
C6 C 0.39652(19) 0.32088(15) 0.62103(18) 0.0333(6) Uani 1 1 d . . . . .
H6A H 0.4273 0.3600 0.6693 0.040 Uiso 1 1 calc R U . . .
C25 C 0.6030(2) -0.00959(19) 0.3857(2) 0.0485(8) Uani 1 1 d . . . . .
H25 H 0.6621 0.0169 0.4310 0.058 Uiso 1 1 calc R U . . .
C7 C 0.45745(18) 0.27663(15) 0.59060(18) 0.0305(6) Uani 1 1 d . . . . .
C16 C 0.64027(19) 0.25015(15) 0.62346(18) 0.0320(5) Uani 1 1 d . U . . .
C8 C 0.40957(19) 0.21941(15) 0.51666(18) 0.0316(6) Uani 1 1 d . U . . .
H8 H 0.4488 0.1904 0.4940 0.038 Uiso 1 1 calc R U . . .
C3 C 0.24445(19) 0.24940(15) 0.50952(18) 0.0329(6) Uani 1 1 d . . . . .
H3 H 0.1738 0.2394 0.4834 0.039 Uiso 1 1 calc R U . . .
C15 C 0.74024(19) 0.29008(16) 0.68563(19) 0.0363(6) Uani 1 1 d . . . . .
C13 C 0.9199(2) 0.3190(2) 0.7609(2) 0.0570(8) Uani 1 1 d . U . . .
H13 H 0.9868 0.3077 0.7712 0.068 Uiso 1 1 calc R U . . .
C28 C 0.3322(2) -0.12393(15) 0.18867(18) 0.0327(6) Uani 1 1 d . . . . .
C22 C 0.5222(3) -0.1735(2) 0.1986(2) 0.0556(9) Uani 1 1 d . . . . .
H22 H 0.5845 -0.1891 0.2004 0.067 Uiso 1 1 calc R U . . .
C21 C 0.4342(3) -0.21175(19) 0.1380(2) 0.0566(9) Uani 1 1 d . . . . .
H21 H 0.4371 -0.2542 0.0997 0.068 Uiso 1 1 calc R U . . .
C4 C 0.29045(19) 0.30789(15) 0.58085(18) 0.0318(6) Uani 1 1 d . . . . .
C17 C 0.1548(2) -0.13226(18) 0.1230(2) 0.0468(7) Uani 1 1 d . . . . .
H17 H 0.0927 -0.1129 0.1188 0.056 Uiso 1 1 calc R U . . .
C10 C 0.7233(2) 0.35440(17) 0.7339(2) 0.0401(7) Uani 1 1 d . . . . .
C24 C 0.6105(2) -0.06851(19) 0.3277(2) 0.0490(8) Uani 1 1 d . . . . .
H24 H 0.6748 -0.0819 0.3326 0.059 Uiso 1 1 calc R U . . .
C26 C 0.5056(2) 0.01079(17) 0.3765(2) 0.0416(7) Uani 1 1 d . U . . .
H26 H 0.5014 0.0512 0.4164 0.050 Uiso 1 1 calc R U . . .
C23 C 0.5215(2) -0.10891(17) 0.2608(2) 0.0410(7) Uani 1 1 d . . . . .
C20 C 0.3358(2) -0.18857(16) 0.1310(2) 0.0431(7) Uani 1 1 d . . . . .
C14 C 0.8385(2) 0.27032(18) 0.6979(2) 0.0451(7) Uani 1 1 d . . . . .
H14 H 0.8491 0.2265 0.6653 0.054 Uiso 1 1 calc R U . . .
C9 C 0.61111(19) 0.35863(17) 0.7071(2) 0.0391(7) Uani 1 1 d . . . . .
H9A H 0.5996 0.3485 0.7622 0.047 Uiso 1 1 calc R U . . .
H9B H 0.5823 0.4119 0.6798 0.047 Uiso 1 1 calc R U . . .
C19 C 0.2418(3) -0.22662(19) 0.0694(2) 0.0560(9) Uani 1 1 d . . . . .
H19 H 0.2408 -0.2710 0.0316 0.067 Uiso 1 1 calc R U . . .
C11 C 0.8051(2) 0.40329(19) 0.7964(2) 0.0526(8) Uani 1 1 d . . . . .
H11 H 0.7945 0.4472 0.8289 0.063 Uiso 1 1 calc R U . . .
C12 C 0.9028(2) 0.3841(2) 0.8085(2) 0.0604(9) Uani 1 1 d . U . . .
H12 H 0.9587 0.4160 0.8498 0.073 Uiso 1 1 calc R U . . .
C18 C 0.1518(3) -0.19804(19) 0.0653(2) 0.0569(9) Uani 1 1 d . . . . .
H18 H 0.0889 -0.2224 0.0241 0.068 Uiso 1 1 calc R U . . .
O11 O 0.2383(2) 0.37154(18) 0.3026(2) 0.0906(9) Uani 1 1 d . . . . .
N4 N 0.2400(6) 0.4612(3) 0.4045(3) 0.149(2) Uani 1 1 d . . . . .
C29 C 0.0823(3) 0.3992(3) 0.3231(3) 0.0992(15) Uani 1 1 d . . . . .
H29A H 0.0774 0.3982 0.3818 0.149 Uiso 1 1 calc R U . . .
H29B H 0.0582 0.3477 0.2902 0.149 Uiso 1 1 calc R U . . .
H29C H 0.0406 0.4432 0.2832 0.149 Uiso 1 1 calc R U . . .
C30 C 0.2031(6) 0.4134(3) 0.3470(4) 0.122(2) Uani 1 1 d . . . . .
C31 C 0.1971(5) 0.5185(3) 0.4503(4) 0.136(2) Uani 1 1 d . . . . .
H31A H 0.1707 0.5667 0.4111 0.205 Uiso 1 1 calc R U . . .
H31B H 0.2507 0.5342 0.5123 0.205 Uiso 1 1 calc R U . . .
H31C H 0.1422 0.4918 0.4572 0.205 Uiso 1 1 calc R U . . .
C32 C 0.3621(4) 0.4703(4) 0.4378(4) 0.147(3) Uani 1 1 d . . . . .
H32A H 0.4009 0.4511 0.5026 0.221 Uiso 1 1 calc R U . . .
H32B H 0.3783 0.5272 0.4344 0.221 Uiso 1 1 calc R U . . .
H32C H 0.3799 0.4382 0.3964 0.221 Uiso 1 1 calc R U . . .
H9WA H 0.138(2) 0.423(2) -0.020(2) 0.057(11) Uiso 1 1 d . . . . .
H8A H 0.104(3) 0.273(2) 0.119(3) 0.074(14) Uiso 1 1 d . . . . .
H8B H 0.138(3) 0.328(2) 0.186(3) 0.092(16) Uiso 1 1 d . . . . .
H9WB H 0.114(3) 0.408(2) 0.054(3) 0.089(15) Uiso 1 1 d . . . . .
H1WB H 0.045(3) 0.626(3) 0.919(3) 0.103(16) Uiso 1 1 d . . . . .
H6WA H 0.279(2) -0.1003(19) 0.392(2) 0.056(10) Uiso 1 1 d . . . . .
H1WA H 0.103(3) 0.562(3) 0.969(3) 0.105(19) Uiso 1 1 d . . . . .
H7WA H 0.098(3) 0.084(2) 0.169(3) 0.082(13) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C5 O4 1.252(3) . ?
C5 O3 1.261(3) . ?
C5 C4 1.512(3) . ?
O8 H8A 0.80(4) . ?
O8 H8B 0.89(4) . ?
O10 H1WB 0.88(4) . ?
O10 H1WA 0.79(5) . ?
O9 H9WA 0.82(3) . ?
O9 H9WB 0.89(4) . ?
Co1 O3 2.0498(18) 4_565 ?
Co1 O1 2.0641(17) . ?
Co1 O6 2.097(2) . ?
Co1 N2 2.145(2) . ?
Co1 O7 2.1513(19) . ?
Co1 N1 2.153(2) . ?
O7 H7WB 0.8200 . ?
O7 H7WA 0.84(4) . ?
O3 Co1 2.0498(18) 4_566 ?
O6 H6WB 0.8200 . ?
O6 H6WA 0.81(3) . ?
O1 C1 1.266(3) . ?
O5 C16 1.234(3) . ?
N2 C26 1.329(3) . ?
N2 C27 1.354(3) . ?
O2 C1 1.255(3) . ?
N1 C17 1.328(3) . ?
N1 C28 1.360(3) . ?
N3 C16 1.371(3) . ?
N3 C7 1.425(3) . ?
N3 C9 1.471(3) . ?
C2 C8 1.387(3) . ?
C2 C3 1.391(3) . ?
C2 C1 1.504(3) . ?
C27 C23 1.411(4) . ?
C27 C28 1.440(3) . ?
C6 C7 1.389(3) . ?
C6 C4 1.389(3) . ?
C6 H6A 0.9300 . ?
C25 C24 1.360(4) . ?
C25 C26 1.398(4) . ?
C25 H25 0.9300 . ?
C7 C8 1.397(3) . ?
C16 C15 1.476(3) . ?
C8 H8 0.9300 . ?
C3 C4 1.383(3) . ?
C3 H3 0.9300 . ?
C15 C10 1.379(4) . ?
C15 C14 1.391(4) . ?
C13 C12 1.383(5) . ?
C13 C14 1.387(4) . ?
C13 H13 0.9300 . ?
C28 C20 1.404(4) . ?
C22 C21 1.344(4) . ?
C22 C23 1.438(4) . ?
C22 H22 0.9300 . ?
C21 C20 1.437(4) . ?
C21 H21 0.9300 . ?
C17 C18 1.389(4) . ?
C17 H17 0.9300 . ?
C10 C11 1.390(4) . ?
C10 C9 1.490(4) . ?
C24 C23 1.399(4) . ?
C24 H24 0.9300 . ?
C26 H26 0.9300 . ?
C20 C19 1.403(4) . ?
C14 H14 0.9300 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C19 C18 1.365(4) . ?
C19 H19 0.9300 . ?
C11 C12 1.383(4) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C18 H18 0.9300 . ?
O11 C30 1.243(6) . ?
N4 C30 1.121(6) . ?
N4 C31 1.481(7) . ?
N4 C32 1.613(8) . ?
C29 C30 1.638(8) . ?
C29 H29A 0.9600 . ?
C29 H29B 0.9600 . ?
C29 H29C 0.9600 . ?
C31 H31A 0.9600 . ?
C31 H31B 0.9600 . ?
C31 H31C 0.9600 . ?
C32 H32A 0.9600 . ?
C32 H32B 0.9600 . ?
C32 H32C 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 C5 O3 125.4(2) . . ?
O4 C5 C4 119.8(2) . . ?
O3 C5 C4 114.8(2) . . ?
H8A O8 H8B 100(4) . . ?
H1WB O10 H1WA 106(4) . . ?
H9WA O9 H9WB 107(3) . . ?
O3 Co1 O1 92.35(8) 4_565 . ?
O3 Co1 O6 177.20(8) 4_565 . ?
O1 Co1 O6 90.33(8) . . ?
O3 Co1 N2 85.13(8) 4_565 . ?
O1 Co1 N2 93.08(7) . . ?
O6 Co1 N2 95.52(8) . . ?
O3 Co1 O7 89.01(8) 4_565 . ?
O1 Co1 O7 93.23(7) . . ?
O6 Co1 O7 90.04(8) . . ?
N2 Co1 O7 171.55(8) . . ?
O3 Co1 N1 87.68(8) 4_565 . ?
O1 Co1 N1 170.43(7) . . ?
O6 Co1 N1 89.80(8) . . ?
N2 Co1 N1 77.38(8) . . ?
O7 Co1 N1 96.34(8) . . ?
Co1 O7 H7WB 109.5 . . ?
Co1 O7 H7WA 102(2) . . ?
H7WB O7 H7WA 96.5 . . ?
C5 O3 Co1 133.09(17) . 4_566 ?
Co1 O6 H6WB 109.5 . . ?
Co1 O6 H6WA 118(2) . . ?
H6WB O6 H6WA 119.3 . . ?
C1 O1 Co1 124.24(16) . . ?
C26 N2 C27 117.8(2) . . ?
C26 N2 Co1 127.97(19) . . ?
C27 N2 Co1 113.28(16) . . ?
C17 N1 C28 117.9(2) . . ?
C17 N1 Co1 128.66(19) . . ?
C28 N1 Co1 113.20(16) . . ?
C16 N3 C7 127.4(2) . . ?
C16 N3 C9 111.7(2) . . ?
C7 N3 C9 120.9(2) . . ?
C8 C2 C3 120.1(2) . . ?
C8 C2 C1 120.1(2) . . ?
C3 C2 C1 119.8(2) . . ?
O2 C1 O1 124.7(2) . . ?
O2 C1 C2 117.8(2) . . ?
O1 C1 C2 117.5(2) . . ?
N2 C27 C23 123.1(2) . . ?
N2 C27 C28 117.5(2) . . ?
C23 C27 C28 119.4(2) . . ?
C7 C6 C4 121.3(2) . . ?
C7 C6 H6A 119.3 . . ?
C4 C6 H6A 119.3 . . ?
C24 C25 C26 119.3(3) . . ?
C24 C25 H25 120.3 . . ?
C26 C25 H25 120.3 . . ?
C6 C7 C8 118.6(2) . . ?
C6 C7 N3 118.4(2) . . ?
C8 C7 N3 123.1(2) . . ?
O5 C16 N3 125.9(2) . . ?
O5 C16 C15 127.2(2) . . ?
N3 C16 C15 106.8(2) . . ?
C2 C8 C7 120.4(2) . . ?
C2 C8 H8 119.8 . . ?
C7 C8 H8 119.8 . . ?
C4 C3 C2 120.0(2) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C10 C15 C14 122.3(2) . . ?
C10 C15 C16 108.9(2) . . ?
C14 C15 C16 128.9(3) . . ?
C12 C13 C14 120.9(3) . . ?
C12 C13 H13 119.6 . . ?
C14 C13 H13 119.6 . . ?
N1 C28 C20 122.7(2) . . ?
N1 C28 C27 117.2(2) . . ?
C20 C28 C27 120.1(2) . . ?
C21 C22 C23 120.9(3) . . ?
C21 C22 H22 119.5 . . ?
C23 C22 H22 119.5 . . ?
C22 C21 C20 121.7(3) . . ?
C22 C21 H21 119.2 . . ?
C20 C21 H21 119.2 . . ?
C3 C4 C6 119.5(2) . . ?
C3 C4 C5 122.2(2) . . ?
C6 C4 C5 118.3(2) . . ?
N1 C17 C18 123.0(3) . . ?
N1 C17 H17 118.5 . . ?
C18 C17 H17 118.5 . . ?
C15 C10 C11 120.6(3) . . ?
C15 C10 C9 109.4(2) . . ?
C11 C10 C9 130.0(3) . . ?
C25 C24 C23 120.0(3) . . ?
C25 C24 H24 120.0 . . ?
C23 C24 H24 120.0 . . ?
N2 C26 C25 122.8(3) . . ?
N2 C26 H26 118.6 . . ?
C25 C26 H26 118.6 . . ?
C24 C23 C27 117.0(3) . . ?
C24 C23 C22 123.9(3) . . ?
C27 C23 C22 119.2(3) . . ?
C19 C20 C28 117.3(3) . . ?
C19 C20 C21 124.0(3) . . ?
C28 C20 C21 118.7(3) . . ?
C13 C14 C15 116.9(3) . . ?
C13 C14 H14 121.5 . . ?
C15 C14 H14 121.5 . . ?
N3 C9 C10 103.2(2) . . ?
N3 C9 H9A 111.1 . . ?
C10 C9 H9A 111.1 . . ?
N3 C9 H9B 111.1 . . ?
C10 C9 H9B 111.1 . . ?
H9A C9 H9B 109.1 . . ?
C18 C19 C20 119.5(3) . . ?
C18 C19 H19 120.2 . . ?
C20 C19 H19 120.2 . . ?
C12 C11 C10 117.4(3) . . ?
C12 C11 H11 121.3 . . ?
C10 C11 H11 121.3 . . ?
C13 C12 C11 122.0(3) . . ?
C13 C12 H12 119.0 . . ?
C11 C12 H12 119.0 . . ?
C19 C18 C17 119.5(3) . . ?
C19 C18 H18 120.3 . . ?
C17 C18 H18 120.3 . . ?
C30 N4 C31 132.4(8) . . ?
C30 N4 C32 111.8(7) . . ?
C31 N4 C32 115.8(5) . . ?
C30 C29 H29A 109.5 . . ?
C30 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C30 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
N4 C30 O11 131.5(8) . . ?
N4 C30 C29 110.2(7) . . ?
O11 C30 C29 118.3(5) . . ?
N4 C31 H31A 109.5 . . ?
N4 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
N4 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
N4 C32 H32A 109.5 . . ?
N4 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
N4 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 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
O4 C5 O3 Co1 27.2(4) . . . 4_566 ?
C4 C5 O3 Co1 -154.30(17) . . . 4_566 ?
Co1 O1 C1 O2 -8.0(4) . . . . ?
Co1 O1 C1 C2 170.73(16) . . . . ?
C8 C2 C1 O2 170.1(2) . . . . ?
C3 C2 C1 O2 -9.5(4) . . . . ?
C8 C2 C1 O1 -8.8(4) . . . . ?
C3 C2 C1 O1 171.7(2) . . . . ?
C26 N2 C27 C23 -0.7(4) . . . . ?
Co1 N2 C27 C23 169.29(19) . . . . ?
C26 N2 C27 C28 179.1(2) . . . . ?
Co1 N2 C27 C28 -10.9(3) . . . . ?
C4 C6 C7 C8 1.4(4) . . . . ?
C4 C6 C7 N3 -179.6(2) . . . . ?
C16 N3 C7 C6 172.4(2) . . . . ?
C9 N3 C7 C6 -4.4(4) . . . . ?
C16 N3 C7 C8 -8.6(4) . . . . ?
C9 N3 C7 C8 174.6(2) . . . . ?
C7 N3 C16 O5 0.6(4) . . . . ?
C9 N3 C16 O5 177.7(2) . . . . ?
C7 N3 C16 C15 -179.6(2) . . . . ?
C9 N3 C16 C15 -2.5(3) . . . . ?
C3 C2 C8 C7 0.9(4) . . . . ?
C1 C2 C8 C7 -178.7(2) . . . . ?
C6 C7 C8 C2 -2.0(4) . . . . ?
N3 C7 C8 C2 179.0(2) . . . . ?
C8 C2 C3 C4 1.0(4) . . . . ?
C1 C2 C3 C4 -179.5(2) . . . . ?
O5 C16 C15 C10 -179.4(3) . . . . ?
N3 C16 C15 C10 0.8(3) . . . . ?
O5 C16 C15 C14 0.6(5) . . . . ?
N3 C16 C15 C14 -179.2(3) . . . . ?
C17 N1 C28 C20 1.1(4) . . . . ?
Co1 N1 C28 C20 -173.5(2) . . . . ?
C17 N1 C28 C27 -179.1(2) . . . . ?
Co1 N1 C28 C27 6.4(3) . . . . ?
N2 C27 C28 N1 3.1(3) . . . . ?
C23 C27 C28 N1 -177.1(2) . . . . ?
N2 C27 C28 C20 -177.0(2) . . . . ?
C23 C27 C28 C20 2.7(4) . . . . ?
C23 C22 C21 C20 1.5(5) . . . . ?
C2 C3 C4 C6 -1.6(4) . . . . ?
C2 C3 C4 C5 177.8(2) . . . . ?
C7 C6 C4 C3 0.4(4) . . . . ?
C7 C6 C4 C5 -179.0(2) . . . . ?
O4 C5 C4 C3 12.9(4) . . . . ?
O3 C5 C4 C3 -165.7(2) . . . . ?
O4 C5 C4 C6 -167.8(2) . . . . ?
O3 C5 C4 C6 13.6(3) . . . . ?
C28 N1 C17 C18 0.7(4) . . . . ?
Co1 N1 C17 C18 174.3(2) . . . . ?
C14 C15 C10 C11 1.0(4) . . . . ?
C16 C15 C10 C11 -179.0(2) . . . . ?
C14 C15 C10 C9 -178.8(2) . . . . ?
C16 C15 C10 C9 1.2(3) . . . . ?
C26 C25 C24 C23 -1.0(4) . . . . ?
C27 N2 C26 C25 0.8(4) . . . . ?
Co1 N2 C26 C25 -167.5(2) . . . . ?
C24 C25 C26 N2 0.1(4) . . . . ?
C25 C24 C23 C27 1.0(4) . . . . ?
C25 C24 C23 C22 -178.1(3) . . . . ?
N2 C27 C23 C24 -0.2(4) . . . . ?
C28 C27 C23 C24 -180.0(2) . . . . ?
N2 C27 C23 C22 179.0(3) . . . . ?
C28 C27 C23 C22 -0.8(4) . . . . ?
C21 C22 C23 C24 177.8(3) . . . . ?
C21 C22 C23 C27 -1.3(4) . . . . ?
N1 C28 C20 C19 -2.6(4) . . . . ?
C27 C28 C20 C19 177.5(2) . . . . ?
N1 C28 C20 C21 177.3(2) . . . . ?
C27 C28 C20 C21 -2.6(4) . . . . ?
C22 C21 C20 C19 -179.7(3) . . . . ?
C22 C21 C20 C28 0.5(5) . . . . ?
C12 C13 C14 C15 -0.2(5) . . . . ?
C10 C15 C14 C13 -0.5(4) . . . . ?
C16 C15 C14 C13 179.4(3) . . . . ?
C16 N3 C9 C10 3.2(3) . . . . ?
C7 N3 C9 C10 -179.6(2) . . . . ?
C15 C10 C9 N3 -2.6(3) . . . . ?
C11 C10 C9 N3 177.6(3) . . . . ?
C28 C20 C19 C18 2.4(4) . . . . ?
C21 C20 C19 C18 -177.5(3) . . . . ?
C15 C10 C11 C12 -0.6(4) . . . . ?
C9 C10 C11 C12 179.2(3) . . . . ?
C14 C13 C12 C11 0.6(5) . . . . ?
C10 C11 C12 C13 -0.1(5) . . . . ?
C20 C19 C18 C17 -0.7(5) . . . . ?
N1 C17 C18 C19 -0.9(5) . . . . ?
C31 N4 C30 O11 171.8(5) . . . . ?
C32 N4 C30 O11 -4.6(8) . . . . ?
C31 N4 C30 C29 -9.5(8) . . . . ?
C32 N4 C30 C29 174.1(3) . . . . ?

_refine_diff_density_max         0.630
_refine_diff_density_min         -0.454
_refine_diff_density_rms         0.052

_shelxl_version_number           2014-3

####################################################################### 
# 
# 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_2
_database_code_depnum_ccdc_archive 'CCDC 1503569'
_audit_update_record             
;
2016-11-30 deposited with the CCDC.
2016-12-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C57 H46 N6 O15 S0 Zn2'
_chemical_formula_weight         1185.74

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn 0.2839 1.4301 '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                   9.5056(4)
_cell_length_b                   37.3101(15)
_cell_length_c                   14.7360(6)
_cell_angle_alpha                90
_cell_angle_beta                 96.3050(10)
_cell_angle_gamma                90
_cell_volume                     5194.6(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9152
_cell_measurement_theta_min      1
_cell_measurement_theta_max      24.999

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.516
_exptl_crystal_F_000             2440
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.16
_exptl_absorpt_coefficient_mu    1.002
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker SMART APEX CCD'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            26528
_diffrn_reflns_av_unetI/netI     0.0542
_diffrn_reflns_av_R_equivalents  0.0458
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       44
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.092
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 0.974
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 0.974
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 0.974
_reflns_number_total             9152
_reflns_number_gt                6558
_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       ?
_computing_data_reduction        ?
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014 (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)+(0.0491P)²+14.8206P] 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         9152
_refine_ls_number_parameters     738
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.0967
_refine_ls_R_factor_gt           0.0675
_refine_ls_wR_factor_ref         0.1671
_refine_ls_wR_factor_gt          0.1580
_refine_ls_goodness_of_fit_ref   1.104
_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
O13 O 0.9802(9) 0.24605(16) 0.7161(4) 0.111(2) Uani 1 1 d G . . . .
H13A H 0.9033 0.2573 0.7017 0.167 Uiso 1 1 d G U . . .
H13B H 1.0004 0.2465 0.7737 0.167 Uiso 1 1 d G U . . .
O8 O -0.2127(5) 1.25044(10) 1.0112(3) 0.0619(12) Uani 1 1 d . . . . .
O7 O -0.1162(6) 1.25326(12) 0.8824(4) 0.0786(16) Uani 1 1 d . . . . .
C74 C -0.1625(7) 1.23623(16) 0.9434(4) 0.0486(15) Uani 1 1 d . . . . .
Zn1 Zn 0.05456(7) 1.05845(2) 0.71530(4) 0.03649(18) Uani 1 1 d . . . . .
Zn2 Zn 0.24153(7) 0.80289(2) 0.49970(4) 0.04200(19) Uani 1 1 d . . . . .
O6 O -0.0362(4) 1.08663(9) 0.8059(3) 0.0457(10) Uani 1 1 d . . . . .
O11 O -0.0961(5) 1.06125(12) 0.6049(3) 0.0556(11) Uani 1 1 d D . . . .
N4 N 0.2156(5) 1.08191(12) 0.6444(3) 0.0427(11) Uani 1 1 d . . . . .
O4 O 0.1583(5) 0.83636(10) 0.5809(3) 0.0590(12) Uani 1 1 d . . . . .
O1 O -0.0181(5) 1.00693(10) 0.7537(3) 0.0535(11) Uani 1 1 d . . . . .
N3 N 0.2419(5) 1.05257(12) 0.8111(3) 0.0413(11) Uani 1 1 d . . . . .
O3 O 0.2050(5) 0.88398(11) 0.5001(3) 0.0553(11) Uani 1 1 d . . . . .
C8 C 0.1003(6) 0.92896(14) 0.6357(4) 0.0404(13) Uani 1 1 d . . . . .
H8 H 0.1481 0.9405 0.5923 0.049 Uiso 1 1 calc R U . . .
C9 C -0.1031(6) 1.14047(14) 0.8728(4) 0.0424(14) Uani 1 1 d . . . . .
C10 C -0.1556(6) 1.12166(15) 0.9418(4) 0.0458(14) Uani 1 1 d . . . . .
H10 H -0.1527 1.0967 0.9415 0.055 Uiso 1 1 calc R U . . .
C11 C 0.1578(6) 0.86969(15) 0.5656(4) 0.0396(13) Uani 1 1 d . . . . .
C12 C -0.0458(6) 1.12002(15) 0.7955(4) 0.0424(13) Uani 1 1 d . . . . .
C13 C 0.0387(6) 0.94884(14) 0.7000(4) 0.0423(14) Uani 1 1 d . . . . .
C14 C 0.0499(7) 0.98908(15) 0.7015(4) 0.0463(14) Uani 1 1 d . . . . .
O2 O 0.1288(5) 1.00385(10) 0.6502(3) 0.0581(12) Uani 1 1 d . . . . .
O12 O 0.0970(5) 0.80998(11) 0.3858(3) 0.0696(14) Uani 1 1 d . . . . .
H12A H 0.0872 0.7906 0.3556 0.104 Uiso 1 1 d R U . . .
H12B H 0.1282 0.8262 0.3528 0.104 Uiso 1 1 d R U . . .
C18 C -0.2299(10) 0.8042(2) 0.9705(5) 0.078(2) Uani 1 1 d . . . . .
H18 H -0.1899 0.7825 0.9562 0.094 Uiso 1 1 calc R U . . .
C19 C -0.1056(6) 1.17747(15) 0.8725(4) 0.0468(14) Uani 1 1 d . . . . .
H19 H -0.0717 1.1900 0.8248 0.056 Uiso 1 1 calc R U . . .
C20 C -0.3986(9) 1.04525(19) 1.2049(5) 0.071(2) Uani 1 1 d . . . . .
H20 H -0.3658 1.0236 1.1837 0.085 Uiso 1 1 calc R U . . .
C21 C 0.0910(6) 0.89198(14) 0.6357(4) 0.0373(12) Uani 1 1 d . . . . .
C22 C 0.0216(6) 0.87467(14) 0.7015(4) 0.0430(14) Uani 1 1 d . . . . .
H22 H 0.0145 0.8498 0.7008 0.052 Uiso 1 1 calc R U . . .
O5 O -0.0106(5) 1.13634(11) 0.7289(3) 0.0652(13) Uani 1 1 d . . . . .
C24 C -0.2146(7) 1.17668(15) 1.0112(4) 0.0486(15) Uani 1 1 d . . . . .
H24 H -0.2541 1.1890 1.0571 0.058 Uiso 1 1 calc R U . . .
C25 C 0.4973(7) 1.05668(17) 0.8221(5) 0.0579(17) Uani 1 1 d . . . . .
N5 N -0.1044(5) 0.87691(12) 0.8372(3) 0.0474(12) Uani 1 1 d . . . . .
N6 N -0.2718(6) 1.12079(12) 1.0828(3) 0.0485(13) Uani 1 1 d . . . . .
C28 C 0.3630(6) 1.06158(15) 0.7749(4) 0.0449(14) Uani 1 1 d . . . . .
C29 C -0.2131(6) 1.13937(14) 1.0121(4) 0.0424(14) Uani 1 1 d . . . . .
C30 C -0.1582(7) 1.19587(14) 0.9428(4) 0.0453(14) Uani 1 1 d . . . . .
C31 C -0.0370(6) 0.89412(14) 0.7680(4) 0.0402(13) Uani 1 1 d . . . . .
N2 N 0.4186(7) 0.79466(15) 0.6055(4) 0.0648(15) Uani 1 1 d . . . . .
C33 C -0.2730(7) 1.08416(16) 1.0958(4) 0.0483(15) Uani 1 1 d . . . . .
C34 C 0.3475(6) 1.07716(15) 0.6855(4) 0.0462(14) Uani 1 1 d . . . . .
C35 C -0.0308(6) 0.93152(14) 0.7657(4) 0.0415(13) Uani 1 1 d . . . . .
H35 H -0.0734 0.9449 0.8084 0.050 Uiso 1 1 calc R U . . .
C36 C -0.3619(7) 1.07756(16) 1.1695(4) 0.0517(16) Uani 1 1 d . . . . .
C37 C -0.4062(7) 1.10946(17) 1.2023(4) 0.0564(17) Uani 1 1 d . . . . .
C38 C -0.1874(8) 0.89705(17) 0.8977(4) 0.0597(18) Uani 1 1 d . . . . .
H38A H -0.2623 0.9106 0.8632 0.072 Uiso 1 1 calc R U . . .
H38B H -0.1281 0.9133 0.9364 0.072 Uiso 1 1 calc R U . . .
C39 C -0.0998(7) 0.84095(16) 0.8575(4) 0.0512(15) Uani 1 1 d . . . . .
C40 C 0.5498(8) 0.80384(18) 0.4832(7) 0.074(2) Uani 1 1 d . . . . .
C41 C -0.3481(8) 1.13976(16) 1.1509(4) 0.0592(17) Uani 1 1 d . . . . .
H41A H -0.4234 1.1546 1.1215 0.071 Uiso 1 1 calc R U . . .
H41B H -0.2843 1.1545 1.1909 0.071 Uiso 1 1 calc R U . . .
N1 N 0.4191(7) 0.81005(15) 0.4278(4) 0.0735(18) Uani 1 1 d . . . . .
C43 C 0.2526(7) 1.03965(17) 0.8950(4) 0.0561(16) Uani 1 1 d . . . . .
H43 H 0.1701 1.0335 0.9200 0.067 Uiso 1 1 calc R U . . .
C45 C 0.5413(9) 0.79618(18) 0.5765(6) 0.068(2) Uani 1 1 d . . . . .
C46 C 0.4698(7) 1.08679(19) 0.6440(5) 0.0625(19) Uani 1 1 d . . . . .
C47 C 0.1977(8) 1.09678(17) 0.5626(4) 0.0591(17) Uani 1 1 d . . . . .
H47 H 0.1064 1.1006 0.5346 0.071 Uiso 1 1 calc R U . . .
C48 C -0.5332(11) 1.0785(2) 1.3072(6) 0.101(3) Uani 1 1 d . . . . .
H48 H -0.5915 1.0784 1.3540 0.121 Uiso 1 1 calc R U . . .
C49 C 0.3818(9) 1.0348(2) 0.9476(5) 0.071(2) Uani 1 1 d . . . . .
H49 H 0.3856 1.0262 1.0071 0.085 Uiso 1 1 calc R U . . .
C50 C -0.2466(8) 0.86810(18) 0.9528(4) 0.0633(19) Uani 1 1 d . . . . .
C51 C 0.6172(8) 1.0664(2) 0.7771(7) 0.085(3) Uani 1 1 d . . . . .
H51 H 0.7074 1.0625 0.8068 0.102 Uiso 1 1 calc R U . . .
C52 C -0.4870(9) 1.0465(2) 1.2736(5) 0.081(2) Uani 1 1 d . . . . .
H52 H -0.5163 1.0251 1.2979 0.097 Uiso 1 1 calc R U . . .
C53 C 0.5032(8) 1.04272(19) 0.9099(5) 0.071(2) Uani 1 1 d . . . . .
H53 H 0.5906 1.0388 0.9434 0.086 Uiso 1 1 calc R U . . .
C54 C 0.3143(10) 1.1071(2) 0.5166(5) 0.076(2) Uani 1 1 d . . . . .
H54 H 0.2994 1.1173 0.4587 0.091 Uiso 1 1 calc R U . . .
C55 C 0.6042(9) 1.0810(2) 0.6931(7) 0.089(3) Uani 1 1 d . . . . .
H55 H 0.6852 1.0873 0.6668 0.107 Uiso 1 1 calc R U . . .
C56 C 0.5322(13) 0.7800(3) 0.7554(7) 0.107(3) Uani 1 1 d . . . . .
H56 H 0.5251 0.7746 0.8163 0.129 Uiso 1 1 calc R U . . .
C57 C 0.4467(10) 1.1022(2) 0.5568(6) 0.081(2) Uani 1 1 d . . . . .
H57 H 0.5234 1.1090 0.5267 0.097 Uiso 1 1 calc R U . . .
C58 C -0.4928(9) 1.1106(2) 1.2714(5) 0.080(2) Uani 1 1 d . . . . .
H58 H -0.5230 1.1324 1.2932 0.096 Uiso 1 1 calc R U . . .
C59 C -0.1939(7) 0.83563(17) 0.9296(4) 0.0531(16) Uani 1 1 d . . . . .
C60 C 0.6743(10) 0.7896(2) 0.6359(8) 0.087(3) Uani 1 1 d . . . . .
C61 C -0.3455(10) 0.8700(2) 1.0156(5) 0.090(3) Uani 1 1 d . . . . .
H61 H -0.3847 0.8917 1.0307 0.108 Uiso 1 1 calc R U . . .
C62 C 0.4210(11) 0.8171(3) 0.3401(6) 0.104(3) Uani 1 1 d D . . . .
H62 H 0.3348 0.8209 0.3050 0.125 Uiso 1 1 calc R U . . .
C63 C 0.4126(11) 0.7868(2) 0.6939(6) 0.091(3) Uani 1 1 d . . . . .
H63 H 0.3242 0.7858 0.7153 0.109 Uiso 1 1 calc R U . . .
C64 C 0.6580(12) 0.7816(2) 0.7219(8) 0.095(3) Uani 1 1 d . . . . .
H64 H 0.7388 0.7767 0.7616 0.114 Uiso 1 1 calc R U . . .
C65 C 0.5460(16) 0.8194(4) 0.2958(10) 0.170(7) Uani 1 1 d D . . . .
H65 H 0.5455 0.8249 0.2342 0.203 Uiso 1 1 calc R U . . .
C66 C 0.6715(18) 0.8127(3) 0.3541(10) 0.142(6) Uani 1 1 d . . . . .
H66 H 0.7571 0.8139 0.3291 0.170 Uiso 1 1 calc R U . . .
O14 O 0.8130(8) 1.0001(2) 0.5226(4) 0.119(2) Uani 1 1 d D U . . .
H14 H 0.8328 0.9994 0.4698 0.178 Uiso 1 1 calc R U . . .
O15 O 0.8570(10) -0.0006(2) 0.9223(6) 0.137(3) Uani 1 1 d G . . . .
H15A H 0.8875 -0.0022 0.8703 0.205 Uiso 1 1 d G U . . .
H15B H 0.9106 0.0132 0.9564 0.205 Uiso 1 1 d G U . . .
O9 O -0.2156(5) 1.06167(11) 1.0529(3) 0.0608(12) Uani 1 1 d . . . . .
C71 C -0.3831(12) 0.8381(3) 1.0546(6) 0.108(3) Uani 1 1 d . . . . .
H71 H -0.4490 0.8386 1.0967 0.130 Uiso 1 1 calc R U . . .
C70 C -0.3273(12) 0.8060(3) 1.0337(6) 0.106(3) Uani 1 1 d . . . . .
H70 H -0.3545 0.7852 1.0618 0.128 Uiso 1 1 calc R U . . .
O10 O -0.0341(6) 0.81812(11) 0.8213(3) 0.0677(13) Uani 1 1 d . . . . .
C101 C 0.8077(10) 0.7990(2) 0.5052(9) 0.101(3) Uani 1 1 d . . . . .
H101 H 0.8953 0.8003 0.4828 0.121 Uiso 1 1 calc R U . . .
C100 C 0.6753(13) 0.8045(2) 0.4436(9) 0.113(4) Uani 1 1 d . . . . .
C102 C 0.7989(12) 0.7921(3) 0.5940(10) 0.120(4) Uani 1 1 d . . . . .
H102 H 0.8836 0.7886 0.6309 0.144 Uiso 1 1 calc R U . . .
C103 C 0.6776(15) 0.9972(4) 0.5229(10) 0.196(6) Uani 1 1 d D U . . .
H10A H 0.6552 0.9956 0.5848 0.294 Uiso 1 1 calc R U . . .
H10B H 0.6450 0.9760 0.4902 0.294 Uiso 1 1 calc R U . . .
H10C H 0.6319 1.0178 0.4941 0.294 Uiso 1 1 calc R U . . .
H11A H -0.123(5) 1.0800(8) 0.575(3) 0.043(17) Uiso 1 1 d D . . . .
H11B H -0.152(6) 1.0444(11) 0.586(4) 0.09(3) Uiso 1 1 d 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
O8 C74 1.269(7) . ?
O8 Zn2 1.980(4) 2_556 ?
O7 C74 1.221(7) . ?
C74 C30 1.506(8) . ?
Zn1 O6 1.971(4) . ?
Zn1 O11 2.048(4) . ?
Zn1 N4 2.134(5) . ?
Zn1 O1 2.140(4) . ?
Zn1 N3 2.159(5) . ?
Zn1 O2 2.391(4) . ?
Zn2 O4 1.956(4) . ?
Zn2 O8 1.980(4) 2_546 ?
Zn2 O12 2.066(4) . ?
Zn2 N1 2.106(6) . ?
Zn2 N2 2.187(6) . ?
O6 C12 1.257(6) . ?
N4 C47 1.321(7) . ?
N4 C34 1.342(7) . ?
O4 C11 1.264(6) . ?
O1 C14 1.251(7) . ?
N3 C43 1.319(7) . ?
N3 C28 1.363(7) . ?
O3 C11 1.230(6) . ?
C8 C21 1.383(7) . ?
C8 C13 1.383(7) . ?
C9 C10 1.375(8) . ?
C9 C19 1.381(8) . ?
C9 C12 1.520(7) . ?
C10 C29 1.390(7) . ?
C11 C21 1.519(7) . ?
C12 O5 1.232(7) . ?
C13 C35 1.390(8) . ?
C13 C14 1.505(7) . ?
C14 O2 1.249(7) . ?
C18 C59 1.378(9) . ?
C18 C70 1.384(12) . ?
C19 C30 1.382(8) . ?
C20 C36 1.373(9) . ?
C20 C52 1.386(10) . ?
C21 C22 1.390(8) . ?
C22 C31 1.385(7) . ?
C24 C30 1.392(8) . ?
C24 C29 1.392(8) . ?
C25 C53 1.391(10) . ?
C25 C28 1.397(8) . ?
C25 C51 1.427(10) . ?
N5 C39 1.374(7) . ?
N5 C31 1.417(7) . ?
N5 C38 1.463(7) . ?
N6 C33 1.381(7) . ?
N6 C29 1.416(7) . ?
N6 C41 1.482(7) . ?
C28 C34 1.434(8) . ?
C31 C35 1.397(7) . ?
N2 C45 1.286(9) . ?
N2 C63 1.342(10) . ?
C33 O9 1.216(7) . ?
C33 C36 1.469(8) . ?
C34 C46 1.418(8) . ?
C36 C37 1.368(8) . ?
C37 C58 1.378(9) . ?
C37 C41 1.499(9) . ?
C38 C50 1.497(8) . ?
C39 O10 1.213(7) . ?
C39 C59 1.476(9) . ?
C40 C100 1.385(12) . ?
C40 C45 1.416(11) . ?
C40 N1 1.427(10) . ?
N1 C62 1.322(10) . ?
C43 C49 1.391(9) . ?
C45 C60 1.477(11) . ?
C46 C57 1.401(10) . ?
C46 C55 1.415(11) . ?
C47 C54 1.414(9) . ?
C48 C52 1.384(11) . ?
C48 C58 1.381(11) . ?
C49 C53 1.367(11) . ?
C50 C59 1.369(9) . ?
C50 C61 1.391(10) . ?
C51 C55 1.345(12) . ?
C54 C57 1.344(11) . ?
C56 C64 1.344(14) . ?
C56 C63 1.397(12) . ?
C60 C64 1.328(12) . ?
C60 C102 1.398(14) . ?
C61 C71 1.386(11) . ?
C62 C65 1.419(9) . ?
C65 C66 1.413(18) . ?
C66 C100 1.351(15) . ?
O14 C103 1.292(12) . ?
C71 C70 1.357(12) . ?
C101 C102 1.345(14) . ?
C101 C100 1.482(15) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C74 O8 Zn2 114.2(4) . 2_556 ?
O7 C74 O8 124.0(6) . . ?
O7 C74 C30 120.2(5) . . ?
O8 C74 C30 115.8(6) . . ?
O6 Zn1 O11 101.02(18) . . ?
O6 Zn1 N4 120.27(17) . . ?
O11 Zn1 N4 93.82(19) . . ?
O6 Zn1 O1 96.99(16) . . ?
O11 Zn1 O1 92.18(18) . . ?
N4 Zn1 O1 140.17(17) . . ?
O6 Zn1 N3 90.11(17) . . ?
O11 Zn1 N3 168.26(18) . . ?
N4 Zn1 N3 77.15(18) . . ?
O1 Zn1 N3 90.16(17) . . ?
O6 Zn1 O2 153.72(15) . . ?
O11 Zn1 O2 86.33(17) . . ?
N4 Zn1 O2 83.89(16) . . ?
O1 Zn1 O2 57.25(15) . . ?
N3 Zn1 O2 85.27(16) . . ?
O4 Zn2 O8 128.24(19) . 2_546 ?
O4 Zn2 O12 97.91(19) . . ?
O8 Zn2 O12 89.24(18) 2_546 . ?
O4 Zn2 N1 128.8(2) . . ?
O8 Zn2 N1 101.3(2) 2_546 . ?
O12 Zn2 N1 94.2(2) . . ?
O4 Zn2 N2 89.1(2) . . ?
O8 Zn2 N2 90.5(2) 2_546 . ?
O12 Zn2 N2 171.2(2) . . ?
N1 Zn2 N2 77.3(3) . . ?
C12 O6 Zn1 118.5(4) . . ?
C47 N4 C34 119.2(5) . . ?
C47 N4 Zn1 126.3(5) . . ?
C34 N4 Zn1 114.2(4) . . ?
C11 O4 Zn2 120.9(4) . . ?
C14 O1 Zn1 96.4(4) . . ?
C43 N3 C28 118.4(5) . . ?
C43 N3 Zn1 128.5(4) . . ?
C28 N3 Zn1 113.0(4) . . ?
C21 C8 C13 120.2(5) . . ?
C10 C9 C19 120.4(5) . . ?
C10 C9 C12 119.2(5) . . ?
C19 C9 C12 120.5(5) . . ?
C9 C10 C29 120.9(5) . . ?
O3 C11 O4 124.9(5) . . ?
O3 C11 C21 120.8(5) . . ?
O4 C11 C21 114.3(5) . . ?
O5 C12 O6 124.3(5) . . ?
O5 C12 C9 120.0(5) . . ?
O6 C12 C9 115.7(5) . . ?
C8 C13 C35 119.8(5) . . ?
C8 C13 C14 120.7(5) . . ?
C35 C13 C14 119.5(5) . . ?
O2 C14 O1 121.5(5) . . ?
O2 C14 C13 118.5(5) . . ?
O1 C14 C13 120.0(6) . . ?
C14 O2 Zn1 84.8(3) . . ?
C59 C18 C70 118.0(8) . . ?
C9 C19 C30 120.1(5) . . ?
C36 C20 C52 116.6(7) . . ?
C8 C21 C22 120.0(5) . . ?
C8 C21 C11 121.0(5) . . ?
C22 C21 C11 119.1(5) . . ?
C31 C22 C21 120.6(5) . . ?
C30 C24 C29 121.1(5) . . ?
C53 C25 C28 116.9(7) . . ?
C53 C25 C51 125.1(7) . . ?
C28 C25 C51 118.0(7) . . ?
C39 N5 C31 126.4(5) . . ?
C39 N5 C38 112.1(5) . . ?
C31 N5 C38 121.5(4) . . ?
C33 N6 C29 126.6(5) . . ?
C33 N6 C41 111.5(5) . . ?
C29 N6 C41 121.8(5) . . ?
N3 C28 C25 122.6(6) . . ?
N3 C28 C34 117.0(5) . . ?
C25 C28 C34 120.4(6) . . ?
C10 C29 C24 118.2(5) . . ?
C10 C29 N6 122.3(5) . . ?
C24 C29 N6 119.5(5) . . ?
C19 C30 C24 119.2(5) . . ?
C19 C30 C74 120.9(5) . . ?
C24 C30 C74 119.8(5) . . ?
C22 C31 C35 119.0(5) . . ?
C22 C31 N5 121.4(5) . . ?
C35 C31 N5 119.6(5) . . ?
C45 N2 C63 118.0(8) . . ?
C45 N2 Zn2 114.3(6) . . ?
C63 N2 Zn2 127.6(6) . . ?
O9 C33 N6 126.9(6) . . ?
O9 C33 C36 126.6(6) . . ?
N6 C33 C36 106.4(5) . . ?
N4 C34 C46 122.8(6) . . ?
N4 C34 C28 117.7(5) . . ?
C46 C34 C28 119.5(6) . . ?
C13 C35 C31 120.4(5) . . ?
C37 C36 C20 121.9(6) . . ?
C37 C36 C33 109.9(5) . . ?
C20 C36 C33 128.2(6) . . ?
C36 C37 C58 121.3(6) . . ?
C36 C37 C41 109.4(5) . . ?
C58 C37 C41 129.2(6) . . ?
N5 C38 C50 102.7(5) . . ?
O10 C39 N5 126.6(6) . . ?
O10 C39 C59 127.1(6) . . ?
N5 C39 C59 106.3(5) . . ?
C100 C40 C45 123.8(10) . . ?
C100 C40 N1 119.5(10) . . ?
C45 C40 N1 116.7(6) . . ?
N6 C41 C37 102.5(5) . . ?
C62 N1 C40 119.1(7) . . ?
C62 N1 Zn2 127.9(7) . . ?
C40 N1 Zn2 112.8(5) . . ?
N3 C43 C49 122.8(7) . . ?
N2 C45 C40 118.8(7) . . ?
N2 C45 C60 123.0(8) . . ?
C40 C45 C60 118.2(8) . . ?
C57 C46 C55 125.0(7) . . ?
C57 C46 C34 116.5(7) . . ?
C55 C46 C34 118.5(7) . . ?
N4 C47 C54 121.5(7) . . ?
C52 C48 C58 120.0(8) . . ?
C53 C49 C43 118.6(7) . . ?
C59 C50 C61 120.2(7) . . ?
C59 C50 C38 109.5(6) . . ?
C61 C50 C38 130.2(7) . . ?
C55 C51 C25 122.2(8) . . ?
C48 C52 C20 122.1(7) . . ?
C49 C53 C25 120.7(7) . . ?
C57 C54 C47 119.8(7) . . ?
C51 C55 C46 121.3(7) . . ?
C64 C56 C63 116.6(11) . . ?
C54 C57 C46 120.3(7) . . ?
C37 C58 C48 118.0(7) . . ?
C50 C59 C18 121.9(7) . . ?
C50 C59 C39 109.2(5) . . ?
C18 C59 C39 129.0(6) . . ?
C64 C60 C102 129.0(11) . . ?
C64 C60 C45 114.9(9) . . ?
C102 C60 C45 116.0(11) . . ?
C71 C61 C50 117.1(8) . . ?
N1 C62 C65 124.3(11) . . ?
N2 C63 C56 123.4(10) . . ?
C60 C64 C56 124.1(10) . . ?
C66 C65 C62 113.8(12) . . ?
C100 C66 C65 124.3(13) . . ?
C70 C71 C61 122.5(9) . . ?
C71 C70 C18 120.2(8) . . ?
C102 C101 C100 118.8(10) . . ?
C66 C100 C40 118.9(13) . . ?
C66 C100 C101 124.0(12) . . ?
C40 C100 C101 116.9(11) . . ?
C101 C102 C60 126.1(12) . . ?

_refine_diff_density_max         0.442
_refine_diff_density_min         -0.775
_refine_diff_density_rms         0.071

_shelxl_version_number           2014-3

