# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 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_compound_4
_database_code_depnum_ccdc_archive 'CCDC 1496266'
_audit_update_record             
;
2016-11-11 deposited with the CCDC.
2016-11-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
#_shelx_SHELXL_version_number      '2014/7'
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H11 Co N O6'
_chemical_formula_weight         336.16

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 0.0033 0.0016 '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'
Co Co 0.3494 0.9721 '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                   12.5902(5)
_cell_length_b                   13.8557(6)
_cell_length_c                   7.0755(3)
_cell_angle_alpha                90
_cell_angle_beta                 93.443(4)
_cell_angle_gamma                90
_cell_volume                     1232.07(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4870
_cell_measurement_theta_min      3.354
_cell_measurement_theta_max      25.046

_exptl_crystal_description       block
_exptl_crystal_colour            pink
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.812
_exptl_crystal_F_000             684
_exptl_transmission_factor_min   0.774
_exptl_transmission_factor_max   0.843
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    1.422
_shelx_estimated_absorpt_T_min   0.692
_shelx_estimated_absorpt_T_max   0.848
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
#_exptl_absorpt_special_details    ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APE-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4870
_diffrn_reflns_av_unetI/netI     0.0627
_diffrn_reflns_av_R_equivalents  0.0403
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         3.354
_diffrn_reflns_theta_max         25.046
_diffrn_reflns_theta_full        25.046
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2193
_reflns_number_gt                1696
_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0252P)²+0.1748P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2193
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0588
_refine_ls_R_factor_gt           0.0411
_refine_ls_wR_factor_ref         0.0860
_refine_ls_wR_factor_gt          0.0764
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      1.060
_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 0.22407(4) 0.61223(3) 0.50022(6) 0.02167(17) Uani 1 1 d . . . . .
N1 N 0.3661(2) 0.6226(2) 0.6622(4) 0.0201(6) Uani 1 1 d . . . . .
O1 O 0.31562(18) 0.86941(17) 0.7406(3) 0.0261(6) Uani 1 1 d . . . . .
O2 O 0.23432(17) 0.76233(17) 0.5442(3) 0.0252(6) Uani 1 1 d . . . . .
O3 O 0.92575(18) 0.92791(18) 1.1467(3) 0.0333(6) Uani 1 1 d . . . . .
O4 O 0.76481(18) 0.96797(17) 1.0261(3) 0.0261(6) Uani 1 1 d . . . . .
O5 O 0.1331(2) 0.60787(18) 0.7464(3) 0.0392(7) Uani 1 1 d . . . . .
H1W H 0.1536 0.6534 0.8233 0.047 Uiso 1 1 d R U . . .
H2W H 0.0681 0.5962 0.7156 0.047 Uiso 1 1 d R U . . .
O6 O 0.0852(2) 0.61973(19) 0.3228(4) 0.0426(7) Uani 1 1 d . . . . .
H3W H 0.0537 0.5622 0.3519 0.051 Uiso 1 1 d R U . . .
H4W H 0.1097 0.6299 0.2212 0.051 Uiso 1 1 d R U . . .
C1 C 0.3077(3) 0.7886(3) 0.6634(4) 0.0202(8) Uani 1 1 d . . . . .
C2 C 0.3917(3) 0.7132(2) 0.7172(4) 0.0183(8) Uani 1 1 d . . . . .
C3 C 0.4375(3) 0.5528(3) 0.7012(5) 0.0261(8) Uani 1 1 d . . . . .
H3 H 0.4204 0.4899 0.6651 0.031 Uiso 1 1 calc R U . . .
C4 C 0.5358(3) 0.5703(3) 0.7929(5) 0.0271(9) Uani 1 1 d . . . . .
H4 H 0.5835 0.5197 0.8148 0.033 Uiso 1 1 calc R U . . .
C5 C 0.5640(3) 0.6631(3) 0.8529(4) 0.0185(8) Uani 1 1 d . . . . .
C6 C 0.4871(2) 0.7347(3) 0.8132(4) 0.0189(8) Uani 1 1 d . . . . .
H6 H 0.5007 0.7978 0.8525 0.023 Uiso 1 1 calc R U . . .
C7 C 0.6698(3) 0.6853(2) 0.9477(4) 0.0181(8) Uani 1 1 d . . . . .
C8 C 0.7402(3) 0.6109(3) 1.0070(4) 0.0241(8) Uani 1 1 d . . . . .
H8 H 0.7193 0.5468 0.9932 0.029 Uiso 1 1 calc R U . . .
C9 C 0.8404(3) 0.6331(3) 1.0855(5) 0.0270(9) Uani 1 1 d . . . . .
H9 H 0.8867 0.5836 1.1237 0.032 Uiso 1 1 calc R U . . .
C10 C 0.8726(3) 0.7281(3) 1.1081(4) 0.0252(8) Uani 1 1 d . . . . .
H10 H 0.9404 0.7422 1.1601 0.030 Uiso 1 1 calc R U . . .
C11 C 0.8035(3) 0.8022(2) 1.0529(4) 0.0180(8) Uani 1 1 d . . . . .
C12 C 0.8343(3) 0.9058(3) 1.0779(4) 0.0212(8) Uani 1 1 d . . . . .
C13 C 0.7032(2) 0.7797(3) 0.9743(4) 0.0202(8) Uani 1 1 d . . . . .
H13 H 0.6569 0.8296 0.9382 0.024 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Co1 O4 2.013(2) 2_646 ?
Co1 N1 2.071(3) . ?
Co1 O6 2.093(2) . ?
Co1 O2 2.106(2) . ?
Co1 O5 2.142(2) . ?
Co1 O1 2.241(2) 4_575 ?
N1 C3 1.338(4) . ?
N1 C2 1.348(4) . ?
O1 C1 1.247(4) . ?
O1 Co1 2.241(2) 4_576 ?
O2 C1 1.266(4) . ?
O3 C12 1.261(4) . ?
O4 C12 1.267(4) . ?
O4 Co1 2.013(2) 2_656 ?
O5 H1W 0.8621 . ?
O5 H2W 0.8497 . ?
O6 H3W 0.9191 . ?
O6 H4W 0.8121 . ?
C1 C2 1.519(4) . ?
C2 C6 1.376(4) . ?
C3 C4 1.384(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.394(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.402(4) . ?
C5 C7 1.487(4) . ?
C6 H6 0.9300 . ?
C7 C13 1.384(4) . ?
C7 C8 1.407(4) . ?
C8 C9 1.382(4) . ?
C8 H8 0.9300 . ?
C9 C10 1.384(5) . ?
C9 H9 0.9300 . ?
C10 C11 1.387(4) . ?
C10 H10 0.9300 . ?
C11 C13 1.384(4) . ?
C11 C12 1.495(4) . ?
C13 H13 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O4 Co1 N1 93.29(10) 2_646 . ?
O4 Co1 O6 93.10(9) 2_646 . ?
N1 Co1 O6 172.48(11) . . ?
O4 Co1 O2 172.03(9) 2_646 . ?
N1 Co1 O2 78.85(10) . . ?
O6 Co1 O2 94.66(9) . . ?
O4 Co1 O5 95.20(9) 2_646 . ?
N1 Co1 O5 92.19(10) . . ?
O6 Co1 O5 91.19(10) . . ?
O2 Co1 O5 86.49(9) . . ?
O4 Co1 O1 89.71(9) 2_646 4_575 ?
N1 Co1 O1 88.63(10) . 4_575 ?
O6 Co1 O1 87.43(10) . 4_575 ?
O2 Co1 O1 88.80(9) . 4_575 ?
O5 Co1 O1 174.97(9) . 4_575 ?
C3 N1 C2 117.9(3) . . ?
C3 N1 Co1 127.7(2) . . ?
C2 N1 Co1 114.1(2) . . ?
C1 O1 Co1 115.4(2) . 4_576 ?
C1 O2 Co1 114.7(2) . . ?
C12 O4 Co1 130.7(2) . 2_656 ?
Co1 O5 H1W 109.8 . . ?
Co1 O5 H2W 110.5 . . ?
H1W O5 H2W 123.2 . . ?
Co1 O6 H3W 100.3 . . ?
Co1 O6 H4W 101.0 . . ?
H3W O6 H4W 122.8 . . ?
O1 C1 O2 125.9(3) . . ?
O1 C1 C2 118.1(3) . . ?
O2 C1 C2 116.0(3) . . ?
N1 C2 C6 122.0(3) . . ?
N1 C2 C1 114.7(3) . . ?
C6 C2 C1 123.3(3) . . ?
N1 C3 C4 122.7(3) . . ?
N1 C3 H3 118.6 . . ?
C4 C3 H3 118.6 . . ?
C3 C4 C5 120.6(3) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
C4 C5 C6 115.6(3) . . ?
C4 C5 C7 122.2(3) . . ?
C6 C5 C7 122.2(3) . . ?
C2 C6 C5 121.1(3) . . ?
C2 C6 H6 119.4 . . ?
C5 C6 H6 119.4 . . ?
C13 C7 C8 118.1(3) . . ?
C13 C7 C5 120.9(3) . . ?
C8 C7 C5 121.0(3) . . ?
C9 C8 C7 120.0(3) . . ?
C9 C8 H8 120.0 . . ?
C7 C8 H8 120.0 . . ?
C10 C9 C8 120.8(3) . . ?
C10 C9 H9 119.6 . . ?
C8 C9 H9 119.6 . . ?
C9 C10 C11 119.8(3) . . ?
C9 C10 H10 120.1 . . ?
C11 C10 H10 120.1 . . ?
C10 C11 C13 119.2(3) . . ?
C10 C11 C12 121.6(3) . . ?
C13 C11 C12 119.2(3) . . ?
O3 C12 O4 123.0(3) . . ?
O3 C12 C11 120.3(3) . . ?
O4 C12 C11 116.7(3) . . ?
C7 C13 C11 122.0(3) . . ?
C7 C13 H13 119.0 . . ?
C11 C13 H13 119.0 . . ?

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
Co1 O1 C1 O2 85.1(4) 4_576 . . . ?
Co1 O1 C1 C2 -94.0(3) 4_576 . . . ?
Co1 O2 C1 O1 -164.4(3) . . . . ?
Co1 O2 C1 C2 14.7(3) . . . . ?
C3 N1 C2 C6 -1.0(5) . . . . ?
Co1 N1 C2 C6 -174.9(2) . . . . ?
C3 N1 C2 C1 178.6(3) . . . . ?
Co1 N1 C2 C1 4.7(3) . . . . ?
O1 C1 C2 N1 166.0(3) . . . . ?
O2 C1 C2 N1 -13.2(4) . . . . ?
O1 C1 C2 C6 -14.4(5) . . . . ?
O2 C1 C2 C6 166.4(3) . . . . ?
C2 N1 C3 C4 -0.7(5) . . . . ?
Co1 N1 C3 C4 172.3(2) . . . . ?
N1 C3 C4 C5 1.3(5) . . . . ?
C3 C4 C5 C6 -0.1(5) . . . . ?
C3 C4 C5 C7 -178.5(3) . . . . ?
N1 C2 C6 C5 2.2(5) . . . . ?
C1 C2 C6 C5 -177.4(3) . . . . ?
C4 C5 C6 C2 -1.5(5) . . . . ?
C7 C5 C6 C2 176.8(3) . . . . ?
C4 C5 C7 C13 168.0(3) . . . . ?
C6 C5 C7 C13 -10.2(5) . . . . ?
C4 C5 C7 C8 -9.8(5) . . . . ?
C6 C5 C7 C8 172.0(3) . . . . ?
C13 C7 C8 C9 -1.3(5) . . . . ?
C5 C7 C8 C9 176.5(3) . . . . ?
C7 C8 C9 C10 0.4(5) . . . . ?
C8 C9 C10 C11 0.6(5) . . . . ?
C9 C10 C11 C13 -0.5(5) . . . . ?
C9 C10 C11 C12 178.9(3) . . . . ?
Co1 O4 C12 O3 8.9(5) 2_656 . . . ?
Co1 O4 C12 C11 -170.75(19) 2_656 . . . ?
C10 C11 C12 O3 1.6(5) . . . . ?
C13 C11 C12 O3 -179.0(3) . . . . ?
C10 C11 C12 O4 -178.7(3) . . . . ?
C13 C11 C12 O4 0.7(4) . . . . ?
C8 C7 C13 C11 1.4(5) . . . . ?
C5 C7 C13 C11 -176.5(3) . . . . ?
C10 C11 C13 C7 -0.4(5) . . . . ?
C12 C11 C13 C7 -179.9(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C4 H4 O1 0.93 2.48 3.370(4) 159.6 2_646
C3 H3 O4 0.93 2.64 3.156(4) 115.5 2_646
O6 H4W O2 0.81 2.55 3.245(4) 144.6 4_575
O6 H4W O1 0.81 2.59 2.997(4) 112.8 4_575
O6 H3W O3 0.92 1.88 2.671(4) 143.1 2_646
O5 H2W O3 0.85 1.86 2.709(3) 179.4 4_475
O5 H1W O2 0.86 2.16 2.996(3) 164.5 4_576
C4 H4 O1 0.93 2.48 3.370(4) 159.6 2_646
C3 H3 O4 0.93 2.64 3.156(4) 115.5 2_646
O6 H4W O2 0.81 2.55 3.245(4) 144.6 4_575
O6 H4W O1 0.81 2.59 2.997(4) 112.8 4_575
O6 H3W O3 0.92 1.88 2.671(4) 143.1 2_646
O5 H2W O3 0.85 1.86 2.709(3) 179.4 4_475
O5 H1W O2 0.86 2.16 2.996(3) 164.5 4_576
O6 H4W O2 0.81 2.55 3.245(4) 144.6 4_575
O6 H4W O1 0.81 2.59 2.997(4) 112.8 4_575
O6 H3W O3 0.92 1.88 2.671(4) 143.1 2_646
C4 H4 O1 0.93 2.48 3.370(4) 159.6 2_646
C3 H3 O4 0.93 2.64 3.156(4) 115.5 2_646
O5 H2W O3 0.85 1.86 2.709(3) 179.4 4_475
O5 H1W O2 0.86 2.16 2.996(3) 164.5 4_576
C4 H4 O1 0.93 2.48 3.370(4) 159.6 2_646
C3 H3 O4 0.93 2.64 3.156(4) 115.5 2_646
O5 H2W O3 0.85 1.86 2.709(3) 179.4 4_475
O5 H1W O2 0.86 2.16 2.996(3) 164.5 4_576

_refine_diff_density_max         0.305
_refine_diff_density_min         -0.433
_refine_diff_density_rms         0.081

####################################################################### 
# 
# 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_compound_5
_database_code_depnum_ccdc_archive 'CCDC 1496267'
_audit_update_record             
;
2016-11-11 deposited with the CCDC.
2016-11-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
#_shelx_SHELXL_version_number      '2014/7'
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H19 Co N3 O6'
_chemical_formula_weight         492.34

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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/n'
_space_group_name_Hall           '-P 2yn'

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

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

_cell_length_a                   11.4833(8)
_cell_length_b                   12.8687(6)
_cell_length_c                   15.1022(8)
_cell_angle_alpha                90
_cell_angle_beta                 97.349(6)
_cell_angle_gamma                90
_cell_volume                     2213.4(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    7838
_cell_measurement_theta_min      3.441
_cell_measurement_theta_max      25.048

_exptl_crystal_description       block
_exptl_crystal_colour            pink
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.477
_exptl_crystal_F_000             1012
_exptl_transmission_factor_min   0.795
_exptl_transmission_factor_max   0.821
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.260
_exptl_crystal_size_min          0.240
_exptl_absorpt_coefficient_mu    0.820
_shelx_estimated_absorpt_T_min   0.803
_shelx_estimated_absorpt_T_max   0.827
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
#_exptl_absorpt_special_details    ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APE-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7838
_diffrn_reflns_av_unetI/netI     0.0633
_diffrn_reflns_av_R_equivalents  0.0356
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.441
_diffrn_reflns_theta_max         25.048
_diffrn_reflns_theta_full        25.048
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3925
_reflns_number_gt                2799
_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0228P)²+1.8535P] 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         3925
_refine_ls_number_parameters     306
_refine_ls_number_restraints     7
_refine_ls_R_factor_all          0.0752
_refine_ls_R_factor_gt           0.0478
_refine_ls_wR_factor_ref         0.1006
_refine_ls_wR_factor_gt          0.0865
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_restrained_S_all      1.004
_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 0.22024(4) 0.51497(3) 0.35740(3) 0.03838(16) Uani 1 1 d . . . . .
N1 N 0.3386(2) 0.6423(2) 0.37519(18) 0.0377(7) Uani 1 1 d . . . . .
N2 N 0.0935(3) 0.4036(2) 0.38197(18) 0.0423(7) Uani 1 1 d . . . . .
N3 N 0.0615(3) 0.6043(2) 0.35245(19) 0.0447(8) Uani 1 1 d . . . . .
O1 O 0.2815(2) 0.50616(18) 0.49340(15) 0.0468(6) Uani 1 1 d . U . . .
O2 O 0.4239(2) 0.5585(2) 0.59665(16) 0.0570(7) Uani 1 1 d . . . . .
O3 O 0.6912(2) 0.97286(17) 0.71726(15) 0.0425(6) Uani 1 1 d . . . . .
O4 O 0.8433(3) 1.0598(2) 0.67522(18) 0.0730(9) Uani 1 1 d . . . . .
O5 O 0.3470(3) 0.3972(2) 0.3426(2) 0.0492(7) Uani 1 1 d . . . . .
O6 O 0.5713(3) 0.5526(3) 0.2446(2) 0.1003(12) Uani 1 1 d . . . . .
H3W H 0.5401 0.5258 0.1953 0.120 Uiso 1 1 d R U . . .
H4W H 0.5767 0.5293 0.2971 0.120 Uiso 1 1 d R U . . .
C1 C 0.3660(3) 0.5634(3) 0.5210(2) 0.0431(7) Uani 1 1 d . U . . .
C2 C 0.3977(3) 0.6471(2) 0.4583(2) 0.0359(8) Uani 1 1 d . . . . .
C3 C 0.3618(3) 0.7153(3) 0.3175(2) 0.0471(10) Uani 1 1 d . . . . .
H3 H 0.3223 0.7129 0.2598 0.057 Uiso 1 1 calc R U . . .
C4 C 0.4417(3) 0.7944(3) 0.3390(2) 0.0439(9) Uani 1 1 d . . . . .
H4 H 0.4537 0.8443 0.2966 0.053 Uiso 1 1 calc R U . . .
C5 C 0.5039(3) 0.7995(2) 0.4238(2) 0.0357(8) Uani 1 1 d . . . . .
C6 C 0.4790(3) 0.7225(2) 0.4836(2) 0.0401(9) Uani 1 1 d . . . . .
H6 H 0.5183 0.7224 0.5414 0.048 Uiso 1 1 calc R U . . .
C7 C 0.5945(3) 0.8800(2) 0.4498(2) 0.0390(8) Uani 1 1 d . . . . .
C8 C 0.6262(3) 0.9073(2) 0.5387(2) 0.0361(8) Uani 1 1 d . . . . .
H8 H 0.5872 0.8769 0.5824 0.043 Uiso 1 1 calc R U . . .
C9 C 0.7145(3) 0.9787(2) 0.5636(2) 0.0389(8) Uani 1 1 d . . . . .
C10 C 0.7521(3) 1.0058(3) 0.6594(2) 0.0420(9) Uani 1 1 d . . . . .
C11 C 0.7721(4) 1.0227(3) 0.4976(3) 0.0616(12) Uani 1 1 d . . . . .
H11 H 0.8328 1.0696 0.5136 0.074 Uiso 1 1 calc R U . . .
C12 C 0.7416(4) 0.9987(3) 0.4090(3) 0.0728(14) Uani 1 1 d . . . . .
H12 H 0.7805 1.0294 0.3654 0.087 Uiso 1 1 calc R U . . .
C13 C 0.6523(4) 0.9280(3) 0.3858(3) 0.0594(12) Uani 1 1 d . . . . .
H13 H 0.6304 0.9123 0.3258 0.071 Uiso 1 1 calc R U . . .
C14 C 0.1181(4) 0.3049(3) 0.4055(2) 0.0550(11) Uani 1 1 d . . . . .
H14 H 0.1960 0.2834 0.4133 0.066 Uiso 1 1 calc R U . . .
C15 C 0.0324(5) 0.2346(3) 0.4185(3) 0.0744(14) Uani 1 1 d . . . . .
H15 H 0.0518 0.1668 0.4357 0.089 Uiso 1 1 calc R U . . .
C16 C -0.0829(5) 0.2662(4) 0.4057(4) 0.0940(18) Uani 1 1 d . . . . .
H16 H -0.1427 0.2188 0.4112 0.113 Uiso 1 1 calc R U . . .
C17 C -0.1091(4) 0.3679(3) 0.3847(3) 0.0740(14) Uani 1 1 d . . . . .
H17 H -0.1865 0.3908 0.3774 0.089 Uiso 1 1 calc R U . . .
C18 C -0.0184(3) 0.4360(3) 0.3745(2) 0.0440(9) Uani 1 1 d . . . . .
C19 C -0.0367(3) 0.5481(3) 0.3551(2) 0.0417(9) Uani 1 1 d . . . . .
C20 C -0.1469(4) 0.5925(3) 0.3414(3) 0.0664(12) Uani 1 1 d . . . . .
H20 H -0.2136 0.5524 0.3449 0.080 Uiso 1 1 calc R U . . .
C21 C -0.1566(4) 0.6972(4) 0.3227(3) 0.0834(15) Uani 1 1 d . . . . .
H21 H -0.2301 0.7284 0.3122 0.100 Uiso 1 1 calc R U . . .
C22 C -0.0573(4) 0.7547(3) 0.3196(4) 0.0832(16) Uani 1 1 d . . . . .
H22 H -0.0620 0.8255 0.3076 0.100 Uiso 1 1 calc R U . . .
C23 C 0.0499(4) 0.7057(3) 0.3348(3) 0.0665(13) Uani 1 1 d . . . . .
H23 H 0.1175 0.7450 0.3327 0.080 Uiso 1 1 calc R U . . .
H1W H 0.355(4) 0.401(3) 0.282(3) 0.097(18) Uiso 1 1 d . . . . .
H2W H 0.419(4) 0.410(3) 0.364(3) 0.086(17) 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
Co1 O1 2.087(2) . ?
Co1 O3 2.106(2) 4_575 ?
Co1 N2 2.109(3) . ?
Co1 N1 2.124(3) . ?
Co1 O5 2.133(3) . ?
Co1 N3 2.148(3) . ?
N1 C3 1.332(4) . ?
N1 C2 1.350(4) . ?
N2 C18 1.342(4) . ?
N2 C14 1.339(4) . ?
N3 C23 1.335(4) . ?
N3 C19 1.344(4) . ?
O1 C1 1.246(4) . ?
O2 C1 1.248(4) . ?
O3 C10 1.260(4) . ?
O3 Co1 2.106(2) 4_676 ?
O4 C10 1.255(4) . ?
O5 H1W 0.93(5) . ?
O5 H2W 0.87(5) . ?
O6 H3W 0.8565 . ?
O6 H4W 0.8434 . ?
C1 C2 1.510(5) . ?
C2 C6 1.367(4) . ?
C3 C4 1.380(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.385(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.396(4) . ?
C5 C7 1.485(4) . ?
C6 H6 0.9300 . ?
C7 C13 1.386(5) . ?
C7 C8 1.389(4) . ?
C8 C9 1.384(4) . ?
C8 H8 0.9300 . ?
C9 C11 1.386(5) . ?
C9 C10 1.498(4) . ?
C11 C12 1.374(5) . ?
C11 H11 0.9300 . ?
C12 C13 1.382(5) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C14 C15 1.369(5) . ?
C14 H14 0.9300 . ?
C15 C16 1.374(6) . ?
C15 H15 0.9300 . ?
C16 C17 1.371(6) . ?
C16 H16 0.9300 . ?
C17 C18 1.385(5) . ?
C17 H17 0.9300 . ?
C18 C19 1.483(5) . ?
C19 C20 1.380(5) . ?
C20 C21 1.379(6) . ?
C20 H20 0.9300 . ?
C21 C22 1.365(6) . ?
C21 H21 0.9300 . ?
C22 C23 1.376(6) . ?
C22 H22 0.9300 . ?
C23 H23 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Co1 O3 169.46(10) . 4_575 ?
O1 Co1 N2 86.75(10) . . ?
O3 Co1 N2 101.73(10) 4_575 . ?
O1 Co1 N1 77.74(10) . . ?
O3 Co1 N1 94.95(10) 4_575 . ?
N2 Co1 N1 161.23(11) . . ?
O1 Co1 O5 85.18(11) . . ?
O3 Co1 O5 88.28(11) 4_575 . ?
N2 Co1 O5 91.78(11) . . ?
N1 Co1 O5 97.30(11) . . ?
O1 Co1 N3 103.95(11) . . ?
O3 Co1 N3 84.29(10) 4_575 . ?
N2 Co1 N3 76.59(11) . . ?
N1 Co1 N3 96.79(11) . . ?
O5 Co1 N3 164.58(11) . . ?
C3 N1 C2 117.2(3) . . ?
C3 N1 Co1 129.8(2) . . ?
C2 N1 Co1 113.0(2) . . ?
C18 N2 C14 118.9(3) . . ?
C18 N2 Co1 116.7(2) . . ?
C14 N2 Co1 124.4(3) . . ?
C23 N3 C19 118.0(3) . . ?
C23 N3 Co1 126.3(3) . . ?
C19 N3 Co1 115.0(2) . . ?
C1 O1 Co1 116.6(2) . . ?
C10 O3 Co1 129.9(2) . 4_676 ?
Co1 O5 H1W 103(3) . . ?
Co1 O5 H2W 117(3) . . ?
H1W O5 H2W 98(4) . . ?
H3W O6 H4W 130.4 . . ?
O2 C1 O1 125.3(3) . . ?
O2 C1 C2 117.8(3) . . ?
O1 C1 C2 116.9(3) . . ?
N1 C2 C6 122.5(3) . . ?
N1 C2 C1 114.7(3) . . ?
C6 C2 C1 122.8(3) . . ?
N1 C3 C4 123.3(3) . . ?
N1 C3 H3 118.4 . . ?
C4 C3 H3 118.4 . . ?
C5 C4 C3 120.1(3) . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
C4 C5 C6 116.1(3) . . ?
C4 C5 C7 122.6(3) . . ?
C6 C5 C7 121.2(3) . . ?
C2 C6 C5 120.8(3) . . ?
C2 C6 H6 119.6 . . ?
C5 C6 H6 119.6 . . ?
C13 C7 C8 118.1(3) . . ?
C13 C7 C5 120.5(3) . . ?
C8 C7 C5 121.4(3) . . ?
C9 C8 C7 121.5(3) . . ?
C9 C8 H8 119.3 . . ?
C7 C8 H8 119.3 . . ?
C8 C9 C11 118.5(3) . . ?
C8 C9 C10 121.8(3) . . ?
C11 C9 C10 119.6(3) . . ?
O4 C10 O3 125.4(3) . . ?
O4 C10 C9 116.3(3) . . ?
O3 C10 C9 118.3(3) . . ?
C12 C11 C9 121.4(4) . . ?
C12 C11 H11 119.3 . . ?
C9 C11 H11 119.3 . . ?
C11 C12 C13 119.0(4) . . ?
C11 C12 H12 120.5 . . ?
C13 C12 H12 120.5 . . ?
C12 C13 C7 121.5(4) . . ?
C12 C13 H13 119.3 . . ?
C7 C13 H13 119.3 . . ?
N2 C14 C15 122.3(4) . . ?
N2 C14 H14 118.9 . . ?
C15 C14 H14 118.9 . . ?
C14 C15 C16 118.8(4) . . ?
C14 C15 H15 120.6 . . ?
C16 C15 H15 120.6 . . ?
C17 C16 C15 119.6(4) . . ?
C17 C16 H16 120.2 . . ?
C15 C16 H16 120.2 . . ?
C16 C17 C18 118.9(5) . . ?
C16 C17 H17 120.5 . . ?
C18 C17 H17 120.5 . . ?
N2 C18 C17 121.4(4) . . ?
N2 C18 C19 115.4(3) . . ?
C17 C18 C19 123.2(4) . . ?
N3 C19 C20 122.0(3) . . ?
N3 C19 C18 115.5(3) . . ?
C20 C19 C18 122.4(4) . . ?
C19 C20 C21 118.9(4) . . ?
C19 C20 H20 120.5 . . ?
C21 C20 H20 120.5 . . ?
C22 C21 C20 119.4(4) . . ?
C22 C21 H21 120.3 . . ?
C20 C21 H21 120.3 . . ?
C21 C22 C23 118.7(4) . . ?
C21 C22 H22 120.7 . . ?
C23 C22 H22 120.7 . . ?
N3 C23 C22 123.0(4) . . ?
N3 C23 H23 118.5 . . ?
C22 C23 H23 118.5 . . ?

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
Co1 O1 C1 O2 -169.8(3) . . . . ?
Co1 O1 C1 C2 12.2(4) . . . . ?
C3 N1 C2 C6 -0.5(5) . . . . ?
Co1 N1 C2 C6 179.4(3) . . . . ?
C3 N1 C2 C1 179.0(3) . . . . ?
Co1 N1 C2 C1 -1.2(4) . . . . ?
O2 C1 C2 N1 174.5(3) . . . . ?
O1 C1 C2 N1 -7.3(5) . . . . ?
O2 C1 C2 C6 -6.0(5) . . . . ?
O1 C1 C2 C6 172.2(3) . . . . ?
C2 N1 C3 C4 -0.4(5) . . . . ?
Co1 N1 C3 C4 179.7(3) . . . . ?
N1 C3 C4 C5 1.2(6) . . . . ?
C3 C4 C5 C6 -1.0(5) . . . . ?
C3 C4 C5 C7 177.4(3) . . . . ?
N1 C2 C6 C5 0.7(5) . . . . ?
C1 C2 C6 C5 -178.8(3) . . . . ?
C4 C5 C6 C2 0.1(5) . . . . ?
C7 C5 C6 C2 -178.3(3) . . . . ?
C4 C5 C7 C13 -24.5(5) . . . . ?
C6 C5 C7 C13 153.8(4) . . . . ?
C4 C5 C7 C8 157.4(3) . . . . ?
C6 C5 C7 C8 -24.3(5) . . . . ?
C13 C7 C8 C9 -1.3(5) . . . . ?
C5 C7 C8 C9 176.9(3) . . . . ?
C7 C8 C9 C11 -0.4(5) . . . . ?
C7 C8 C9 C10 -177.8(3) . . . . ?
Co1 O3 C10 O4 -4.3(6) 4_676 . . . ?
Co1 O3 C10 C9 175.4(2) 4_676 . . . ?
C8 C9 C10 O4 170.3(3) . . . . ?
C11 C9 C10 O4 -7.2(5) . . . . ?
C8 C9 C10 O3 -9.4(5) . . . . ?
C11 C9 C10 O3 173.1(3) . . . . ?
C8 C9 C11 C12 1.4(6) . . . . ?
C10 C9 C11 C12 178.9(4) . . . . ?
C9 C11 C12 C13 -0.7(7) . . . . ?
C11 C12 C13 C7 -1.1(7) . . . . ?
C8 C7 C13 C12 2.0(6) . . . . ?
C5 C7 C13 C12 -176.1(4) . . . . ?
C18 N2 C14 C15 2.9(5) . . . . ?
Co1 N2 C14 C15 -178.2(3) . . . . ?
N2 C14 C15 C16 0.9(7) . . . . ?
C14 C15 C16 C17 -3.2(8) . . . . ?
C15 C16 C17 C18 1.7(8) . . . . ?
C14 N2 C18 C17 -4.5(5) . . . . ?
Co1 N2 C18 C17 176.6(3) . . . . ?
C14 N2 C18 C19 175.5(3) . . . . ?
Co1 N2 C18 C19 -3.4(4) . . . . ?
C16 C17 C18 N2 2.2(7) . . . . ?
C16 C17 C18 C19 -177.8(4) . . . . ?
C23 N3 C19 C20 -0.9(5) . . . . ?
Co1 N3 C19 C20 -171.9(3) . . . . ?
C23 N3 C19 C18 179.7(3) . . . . ?
Co1 N3 C19 C18 8.8(4) . . . . ?
N2 C18 C19 N3 -3.7(5) . . . . ?
C17 C18 C19 N3 176.3(4) . . . . ?
N2 C18 C19 C20 177.0(4) . . . . ?
C17 C18 C19 C20 -3.1(6) . . . . ?
N3 C19 C20 C21 1.4(6) . . . . ?
C18 C19 C20 C21 -179.3(4) . . . . ?
C19 C20 C21 C22 -1.2(7) . . . . ?
C20 C21 C22 C23 0.5(8) . . . . ?
C19 N3 C23 C22 0.2(6) . . . . ?
Co1 N3 C23 C22 170.0(4) . . . . ?
C21 C22 C23 N3 0.0(8) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O5 H1W O4 0.93(5) 1.68(5) 2.583(4) 162(4) 4_575
O5 H2W O2 0.87(5) 1.87(5) 2.733(4) 177(4) 3_666
O6 H3W O4 0.86 2.50 3.057(5) 123.7 4_575
O6 H4W O2 0.84 1.96 2.787(4) 165.0 3_666

_refine_diff_density_max         0.250
_refine_diff_density_min         -0.241
_refine_diff_density_rms         0.058

####################################################################### 
# 
# 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_compound_7
_database_code_depnum_ccdc_archive 'CCDC 1496268'
_audit_update_record             
;
2016-11-11 deposited with the CCDC.
2016-11-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
#_shelx_SHELXL_version_number      '2014/7'
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H17 Co N3 O5'
_chemical_formula_weight         498.34

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'
Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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

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

_cell_length_a                   10.0350(3)
_cell_length_b                   11.6320(3)
_cell_length_c                   18.6660(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2178.84(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    7868
_cell_measurement_theta_min      3.458
_cell_measurement_theta_max      25.048

_exptl_crystal_description       block
_exptl_crystal_colour            pink
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.519
_exptl_crystal_F_000             1020
_exptl_transmission_factor_min   0.799
_exptl_transmission_factor_max   0.826
_exptl_crystal_size_max          0.270
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.230
_exptl_absorpt_coefficient_mu    0.832
_shelx_estimated_absorpt_T_min   0.807
_shelx_estimated_absorpt_T_max   0.832
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
#_exptl_absorpt_special_details    ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APE-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7868
_diffrn_reflns_av_unetI/netI     0.0635
_diffrn_reflns_av_R_equivalents  0.0381
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         3.458
_diffrn_reflns_theta_max         25.048
_diffrn_reflns_theta_full        25.048
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             3836
_reflns_number_gt                3341
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.744
_reflns_Friedel_fraction_max     0.992
_reflns_Friedel_fraction_full    0.992

_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0330P)²+0.2400P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1198 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.018(12)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3836
_refine_ls_number_parameters     308
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0501
_refine_ls_R_factor_gt           0.0399
_refine_ls_wR_factor_ref         0.0861
_refine_ls_wR_factor_gt          0.0798
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_restrained_S_all      1.012
_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
Co1 Co 0.38535(6) 0.17463(6) 0.81836(3) 0.02511(18) Uani 1 1 d . . . . .
N1 N 0.5503(4) 0.1858(3) 0.7455(2) 0.0255(9) Uani 1 1 d . . . . .
N2 N 0.2703(4) 0.3148(3) 0.7721(2) 0.0305(10) Uani 1 1 d . . . . .
N3 N 0.2014(4) 0.1611(4) 0.8741(2) 0.0298(10) Uani 1 1 d . . . . .
O1 O 0.3281(3) 0.0633(3) 0.73869(19) 0.0340(9) Uani 1 1 d . . . . .
O2 O 0.3928(4) -0.0229(3) 0.63754(19) 0.0378(9) Uani 1 1 d . . . . .
O3 O 0.8868(4) -0.1289(3) 0.4512(2) 0.0466(10) Uani 1 1 d . . . . .
O4 O 1.0375(4) -0.0406(3) 0.38198(19) 0.0354(9) Uani 1 1 d . . . . .
O5 O 0.4636(4) 0.2898(3) 0.89278(19) 0.0350(9) Uani 1 1 d . . . . .
H1W H 0.4974 0.3507 0.8716 0.052 Uiso 1 1 d R U . . .
H2W H 0.5273 0.2579 0.9179 0.052 Uiso 1 1 d R U . . .
C1 C 0.4089(5) 0.0446(4) 0.6886(3) 0.0272(11) Uani 1 1 d . . . . .
C2 C 0.5378(5) 0.1126(4) 0.6905(3) 0.0246(11) Uani 1 1 d . . . . .
C3 C 0.6612(5) 0.2500(5) 0.7484(3) 0.0351(13) Uani 1 1 d . . . . .
H3 H 0.6717 0.3012 0.7862 0.042 Uiso 1 1 calc R U . . .
C4 C 0.7602(5) 0.2431(4) 0.6975(3) 0.0354(13) Uani 1 1 d . . . . .
H4 H 0.8347 0.2903 0.7015 0.042 Uiso 1 1 calc R U . . .
C5 C 0.7511(5) 0.1674(4) 0.6407(3) 0.0275(11) Uani 1 1 d . . . . .
C6 C 0.6347(5) 0.1012(4) 0.6387(3) 0.0284(12) Uani 1 1 d . . . . .
H6 H 0.6226 0.0486 0.6017 0.034 Uiso 1 1 calc R U . . .
C7 C 0.8543(5) 0.1600(4) 0.5838(3) 0.0320(12) Uani 1 1 d . . . . .
C8 C 0.8610(5) 0.0652(4) 0.5382(3) 0.0284(12) Uani 1 1 d . . . . .
H8 H 0.8027 0.0041 0.5453 0.034 Uiso 1 1 calc R U . . .
C9 C 0.9526(5) 0.0599(4) 0.4826(3) 0.0305(12) Uani 1 1 d . . . . .
C10 C 0.9587(5) -0.0466(4) 0.4349(3) 0.0314(12) Uani 1 1 d . . . . .
C11 C 1.0414(7) 0.1501(5) 0.4739(4) 0.061(2) Uani 1 1 d . . . . .
H11 H 1.1036 0.1477 0.4370 0.074 Uiso 1 1 calc R U . . .
C12 C 1.0383(7) 0.2420(6) 0.5189(4) 0.081(3) Uani 1 1 d . . . . .
H12 H 1.0986 0.3019 0.5128 0.098 Uiso 1 1 calc R U . . .
C13 C 0.9453(7) 0.2467(5) 0.5738(4) 0.063(2) Uani 1 1 d . . . . .
H13 H 0.9446 0.3097 0.6045 0.075 Uiso 1 1 calc R U . . .
C14 C 0.3022(6) 0.3867(4) 0.7203(3) 0.0402(14) Uani 1 1 d . . . . .
H14 H 0.3847 0.3783 0.6982 0.048 Uiso 1 1 calc R U . . .
C15 C 0.2181(6) 0.4750(5) 0.6967(3) 0.0462(16) Uani 1 1 d . . . . .
H15 H 0.2434 0.5228 0.6592 0.055 Uiso 1 1 calc R U . . .
C16 C 0.0977(6) 0.4895(5) 0.7302(3) 0.0472(16) Uani 1 1 d . . . . .
H16 H 0.0413 0.5488 0.7161 0.057 Uiso 1 1 calc R U . . .
C17 C 0.0594(5) 0.4151(4) 0.7857(3) 0.0369(14) Uani 1 1 d . . . . .
C18 C 0.1489(4) 0.3267(4) 0.8045(2) 0.0284(11) Uani 1 1 d . . . . .
C19 C -0.0649(5) 0.4256(5) 0.8237(3) 0.0426(14) Uani 1 1 d . . . . .
H19 H -0.1218 0.4866 0.8136 0.051 Uiso 1 1 calc R U . . .
C20 C -0.0991(5) 0.3482(5) 0.8734(3) 0.0443(15) Uani 1 1 d . . . . .
H20 H -0.1805 0.3559 0.8968 0.053 Uiso 1 1 calc R U . . .
C21 C -0.0135(5) 0.2533(5) 0.8917(3) 0.0357(13) Uani 1 1 d . . . . .
C22 C 0.1136(5) 0.2464(4) 0.8584(2) 0.0272(11) Uani 1 1 d . . . . .
C23 C -0.0466(5) 0.1682(5) 0.9420(3) 0.0439(14) Uani 1 1 d . . . . .
H23 H -0.1290 0.1697 0.9648 0.053 Uiso 1 1 calc R U . . .
C24 C 0.0436(6) 0.0829(5) 0.9571(3) 0.0464(15) Uani 1 1 d . . . . .
H24 H 0.0231 0.0259 0.9903 0.056 Uiso 1 1 calc R U . . .
C25 C 0.1661(6) 0.0828(5) 0.9222(3) 0.0401(15) Uani 1 1 d . . . . .
H25 H 0.2265 0.0247 0.9331 0.048 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Co1 O1 2.054(3) . ?
Co1 O5 2.084(3) . ?
Co1 O4 2.107(3) 2_655 ?
Co1 N3 2.125(4) . ?
Co1 N1 2.147(4) . ?
Co1 N2 2.176(4) . ?
N1 C2 1.340(6) . ?
N1 C3 1.342(6) . ?
N2 C14 1.318(6) . ?
N2 C18 1.367(6) . ?
N3 C25 1.327(6) . ?
N3 C22 1.358(6) . ?
O1 C1 1.257(6) . ?
O2 C1 1.245(6) . ?
O3 C10 1.237(6) . ?
O4 C10 1.267(6) . ?
O4 Co1 2.107(3) 2_654 ?
O5 H1W 0.8783 . ?
O5 H2W 0.8760 . ?
C1 C2 1.516(6) . ?
C2 C6 1.378(7) . ?
C3 C4 1.376(7) . ?
C3 H3 0.9300 . ?
C4 C5 1.381(7) . ?
C4 H4 0.9300 . ?
C5 C6 1.400(6) . ?
C5 C7 1.486(6) . ?
C6 H6 0.9300 . ?
C7 C13 1.373(7) . ?
C7 C8 1.394(7) . ?
C8 C9 1.388(7) . ?
C8 H8 0.9300 . ?
C9 C11 1.386(7) . ?
C9 C10 1.527(7) . ?
C11 C12 1.360(8) . ?
C11 H11 0.9300 . ?
C12 C13 1.388(8) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C14 C15 1.400(7) . ?
C14 H14 0.9300 . ?
C15 C16 1.370(8) . ?
C15 H15 0.9300 . ?
C16 C17 1.404(8) . ?
C16 H16 0.9300 . ?
C17 C18 1.410(7) . ?
C17 C19 1.440(8) . ?
C18 C22 1.419(7) . ?
C19 C20 1.338(8) . ?
C19 H19 0.9300 . ?
C20 C21 1.440(7) . ?
C20 H20 0.9300 . ?
C21 C23 1.403(8) . ?
C21 C22 1.421(7) . ?
C23 C24 1.373(8) . ?
C23 H23 0.9300 . ?
C24 C25 1.392(7) . ?
C24 H24 0.9300 . ?
C25 H25 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Co1 O5 173.50(15) . . ?
O1 Co1 O4 92.54(14) . 2_655 ?
O5 Co1 O4 87.80(13) . 2_655 ?
O1 Co1 N3 93.69(15) . . ?
O5 Co1 N3 92.80(15) . . ?
O4 Co1 N3 89.36(15) 2_655 . ?
O1 Co1 N1 78.18(14) . . ?
O5 Co1 N1 95.34(15) . . ?
O4 Co1 N1 96.81(15) 2_655 . ?
N3 Co1 N1 169.96(15) . . ?
O1 Co1 N2 92.10(15) . . ?
O5 Co1 N2 89.00(14) . . ?
O4 Co1 N2 166.59(15) 2_655 . ?
N3 Co1 N2 77.79(15) . . ?
N1 Co1 N2 96.45(15) . . ?
C2 N1 C3 117.6(4) . . ?
C2 N1 Co1 112.0(3) . . ?
C3 N1 Co1 130.4(3) . . ?
C14 N2 C18 118.4(4) . . ?
C14 N2 Co1 129.6(4) . . ?
C18 N2 Co1 111.9(3) . . ?
C25 N3 C22 118.3(4) . . ?
C25 N3 Co1 127.9(4) . . ?
C22 N3 Co1 113.9(3) . . ?
C1 O1 Co1 117.8(3) . . ?
C10 O4 Co1 128.9(3) . 2_654 ?
Co1 O5 H1W 111.4 . . ?
Co1 O5 H2W 111.1 . . ?
H1W O5 H2W 107.5 . . ?
O2 C1 O1 126.5(4) . . ?
O2 C1 C2 117.2(4) . . ?
O1 C1 C2 116.3(4) . . ?
N1 C2 C6 122.2(4) . . ?
N1 C2 C1 115.4(4) . . ?
C6 C2 C1 122.4(4) . . ?
N1 C3 C4 122.6(5) . . ?
N1 C3 H3 118.7 . . ?
C4 C3 H3 118.7 . . ?
C3 C4 C5 121.3(5) . . ?
C3 C4 H4 119.4 . . ?
C5 C4 H4 119.4 . . ?
C4 C5 C6 115.3(4) . . ?
C4 C5 C7 122.7(4) . . ?
C6 C5 C7 122.0(4) . . ?
C2 C6 C5 121.1(4) . . ?
C2 C6 H6 119.4 . . ?
C5 C6 H6 119.4 . . ?
C13 C7 C8 117.8(5) . . ?
C13 C7 C5 121.2(5) . . ?
C8 C7 C5 121.1(4) . . ?
C9 C8 C7 121.6(4) . . ?
C9 C8 H8 119.2 . . ?
C7 C8 H8 119.2 . . ?
C11 C9 C8 118.7(5) . . ?
C11 C9 C10 121.3(5) . . ?
C8 C9 C10 119.9(4) . . ?
O3 C10 O4 126.8(5) . . ?
O3 C10 C9 117.4(5) . . ?
O4 C10 C9 115.8(5) . . ?
C12 C11 C9 120.5(5) . . ?
C12 C11 H11 119.7 . . ?
C9 C11 H11 119.7 . . ?
C11 C12 C13 120.1(6) . . ?
C11 C12 H12 119.9 . . ?
C13 C12 H12 119.9 . . ?
C7 C13 C12 121.2(6) . . ?
C7 C13 H13 119.4 . . ?
C12 C13 H13 119.4 . . ?
N2 C14 C15 123.4(5) . . ?
N2 C14 H14 118.3 . . ?
C15 C14 H14 118.3 . . ?
C16 C15 C14 118.6(5) . . ?
C16 C15 H15 120.7 . . ?
C14 C15 H15 120.7 . . ?
C15 C16 C17 120.1(5) . . ?
C15 C16 H16 119.9 . . ?
C17 C16 H16 119.9 . . ?
C16 C17 C18 117.3(5) . . ?
C16 C17 C19 123.3(5) . . ?
C18 C17 C19 119.4(5) . . ?
N2 C18 C17 122.1(5) . . ?
N2 C18 C22 118.0(4) . . ?
C17 C18 C22 119.8(4) . . ?
C20 C19 C17 120.5(5) . . ?
C20 C19 H19 119.8 . . ?
C17 C19 H19 119.8 . . ?
C19 C20 C21 121.8(5) . . ?
C19 C20 H20 119.1 . . ?
C21 C20 H20 119.1 . . ?
C23 C21 C22 117.7(5) . . ?
C23 C21 C20 123.9(5) . . ?
C22 C21 C20 118.4(5) . . ?
N3 C22 C18 118.1(4) . . ?
N3 C22 C21 122.0(5) . . ?
C18 C22 C21 119.9(5) . . ?
C24 C23 C21 119.4(5) . . ?
C24 C23 H23 120.3 . . ?
C21 C23 H23 120.3 . . ?
C23 C24 C25 119.1(5) . . ?
C23 C24 H24 120.5 . . ?
C25 C24 H24 120.5 . . ?
N3 C25 C24 123.5(5) . . ?
N3 C25 H25 118.2 . . ?
C24 C25 H25 118.2 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Co1 O1 C1 O2 177.4(4) . . . . ?
Co1 O1 C1 C2 -3.5(5) . . . . ?
C3 N1 C2 C6 0.8(7) . . . . ?
Co1 N1 C2 C6 -177.1(4) . . . . ?
C3 N1 C2 C1 -178.3(4) . . . . ?
Co1 N1 C2 C1 3.8(5) . . . . ?
O2 C1 C2 N1 178.8(4) . . . . ?
O1 C1 C2 N1 -0.4(6) . . . . ?
O2 C1 C2 C6 -0.3(7) . . . . ?
O1 C1 C2 C6 -179.5(4) . . . . ?
C2 N1 C3 C4 0.1(8) . . . . ?
Co1 N1 C3 C4 177.6(4) . . . . ?
N1 C3 C4 C5 -1.0(8) . . . . ?
C3 C4 C5 C6 0.9(7) . . . . ?
C3 C4 C5 C7 178.3(5) . . . . ?
N1 C2 C6 C5 -0.9(7) . . . . ?
C1 C2 C6 C5 178.2(4) . . . . ?
C4 C5 C6 C2 0.0(7) . . . . ?
C7 C5 C6 C2 -177.4(4) . . . . ?
C4 C5 C7 C13 -17.4(8) . . . . ?
C6 C5 C7 C13 159.9(6) . . . . ?
C4 C5 C7 C8 163.3(5) . . . . ?
C6 C5 C7 C8 -19.4(7) . . . . ?
C13 C7 C8 C9 -2.6(8) . . . . ?
C5 C7 C8 C9 176.7(4) . . . . ?
C7 C8 C9 C11 1.8(8) . . . . ?
C7 C8 C9 C10 178.6(5) . . . . ?
Co1 O4 C10 O3 -17.4(8) 2_654 . . . ?
Co1 O4 C10 C9 163.1(3) 2_654 . . . ?
C11 C9 C10 O3 171.7(6) . . . . ?
C8 C9 C10 O3 -5.1(7) . . . . ?
C11 C9 C10 O4 -8.7(8) . . . . ?
C8 C9 C10 O4 174.5(5) . . . . ?
C8 C9 C11 C12 -0.3(10) . . . . ?
C10 C9 C11 C12 -177.1(7) . . . . ?
C9 C11 C12 C13 -0.4(13) . . . . ?
C8 C7 C13 C12 2.0(10) . . . . ?
C5 C7 C13 C12 -177.3(6) . . . . ?
C11 C12 C13 C7 -0.5(12) . . . . ?
C18 N2 C14 C15 0.2(8) . . . . ?
Co1 N2 C14 C15 -178.8(4) . . . . ?
N2 C14 C15 C16 1.6(9) . . . . ?
C14 C15 C16 C17 -1.5(9) . . . . ?
C15 C16 C17 C18 -0.2(8) . . . . ?
C15 C16 C17 C19 179.5(5) . . . . ?
C14 N2 C18 C17 -2.0(7) . . . . ?
Co1 N2 C18 C17 177.1(4) . . . . ?
C14 N2 C18 C22 177.8(4) . . . . ?
Co1 N2 C18 C22 -3.1(5) . . . . ?
C16 C17 C18 N2 2.0(7) . . . . ?
C19 C17 C18 N2 -177.7(4) . . . . ?
C16 C17 C18 C22 -177.7(5) . . . . ?
C19 C17 C18 C22 2.6(7) . . . . ?
C16 C17 C19 C20 176.3(5) . . . . ?
C18 C17 C19 C20 -4.0(8) . . . . ?
C17 C19 C20 C21 1.0(9) . . . . ?
C19 C20 C21 C23 -178.1(5) . . . . ?
C19 C20 C21 C22 3.5(8) . . . . ?
C25 N3 C22 C18 -177.0(4) . . . . ?
Co1 N3 C22 C18 4.8(5) . . . . ?
C25 N3 C22 C21 -0.2(7) . . . . ?
Co1 N3 C22 C21 -178.5(4) . . . . ?
N2 C18 C22 N3 -1.0(6) . . . . ?
C17 C18 C22 N3 178.7(4) . . . . ?
N2 C18 C22 C21 -177.9(4) . . . . ?
C17 C18 C22 C21 1.9(7) . . . . ?
C23 C21 C22 N3 -0.1(7) . . . . ?
C20 C21 C22 N3 178.4(4) . . . . ?
C23 C21 C22 C18 176.6(5) . . . . ?
C20 C21 C22 C18 -4.9(7) . . . . ?
C22 C21 C23 C24 0.2(8) . . . . ?
C20 C21 C23 C24 -178.2(5) . . . . ?
C21 C23 C24 C25 0.0(9) . . . . ?
C22 N3 C25 C24 0.4(8) . . . . ?
Co1 N3 C25 C24 178.4(4) . . . . ?
C23 C24 C25 N3 -0.3(9) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O5 H2W O3 0.88 1.84 2.636(5) 150.4 2_655
O5 H1W O2 0.88 1.85 2.672(5) 156.1 4_656

_refine_diff_density_max         0.325
_refine_diff_density_min         -0.242
_refine_diff_density_rms         0.052

####################################################################### 
# 
# 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_compound_1
_database_code_depnum_ccdc_archive 'CCDC 1498139'
_audit_update_record             
;
2016-11-11 deposited with the CCDC.
2016-11-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
#_shelx_SHELXL_version_number      '2014/7'
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H24 N2 Ni O12'
_chemical_formula_weight         615.18

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 0.0033 0.0016 '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'
Ni Ni 0.3393 1.1124 '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                   12.5528(7)
_cell_length_b                   14.2273(7)
_cell_length_c                   7.1047(4)
_cell_angle_alpha                90
_cell_angle_beta                 93.315(5)
_cell_angle_gamma                90
_cell_volume                     1266.73(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4342
_cell_measurement_theta_min      3.251
_cell_measurement_theta_max      25.049

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.613
_exptl_crystal_F_000             636
_exptl_transmission_factor_min   0.809
_exptl_transmission_factor_max   0.846
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.839
_shelx_estimated_absorpt_T_min   0.799
_shelx_estimated_absorpt_T_max   0.850
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
#_exptl_absorpt_special_details    ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APE-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4342
_diffrn_reflns_av_unetI/netI     0.0812
_diffrn_reflns_av_R_equivalents  0.0496
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         3.251
_diffrn_reflns_theta_max         25.049
_diffrn_reflns_theta_full        25.049
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2239
_reflns_number_gt                1607
_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0229P)²+0.1523P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2239
_refine_ls_number_parameters     188
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0799
_refine_ls_R_factor_gt           0.0498
_refine_ls_wR_factor_ref         0.0995
_refine_ls_wR_factor_gt          0.0831
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_restrained_S_all      1.071
_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
Ni1 Ni 0.5000 0.5000 0.5000 0.0206(2) Uani 1 2 d S . P . .
N1 N 0.3628(2) 0.5678(2) 0.4277(4) 0.0209(7) Uani 1 1 d . . . . .
O1 O 0.56105(18) 0.61481(18) 0.3772(3) 0.0251(6) Uani 1 1 d . . . . .
O2 O 0.51482(19) 0.74563(18) 0.2224(4) 0.0309(7) Uani 1 1 d . . . . .
O3 O -0.2774(2) 0.7924(2) 0.2303(5) 0.0478(9) Uani 1 1 d . . . . .
H3 H -0.3343 0.7646 0.2111 0.072 Uiso 1 1 calc R U . . .
O4 O -0.2091(2) 0.6473(2) 0.2125(4) 0.0468(8) Uani 1 1 d . . . . .
O5 O 0.49844(19) 0.43347(17) 0.2330(3) 0.0320(7) Uani 1 1 d . . . . .
H1W H 0.4947 0.3746 0.2468 0.038 Uiso 1 1 d R U . . .
H2W H 0.4577 0.4507 0.1763 0.038 Uiso 1 1 d R U . . .
O6 O 0.3359(2) 0.4944(2) 0.9735(4) 0.0450(8) Uani 1 1 d D . . . .
H3W H 0.2973 0.4501 0.9207 0.054 Uiso 1 1 d R U . . .
H4W H 0.3856 0.5116 0.9059 0.054 Uiso 1 1 d DR U . . .
C1 C 0.4943(3) 0.6737(3) 0.3125(5) 0.0227(9) Uani 1 1 d . . . . .
C2 C 0.3777(3) 0.6529(3) 0.3494(5) 0.0189(8) Uani 1 1 d . . . . .
C3 C 0.2941(3) 0.7144(3) 0.3100(5) 0.0220(9) Uani 1 1 d . . . . .
H2 H 0.3067 0.7729 0.2571 0.026 Uiso 1 1 calc R U . . .
C4 C 0.1910(3) 0.6883(3) 0.3499(5) 0.0219(9) Uani 1 1 d . . . . .
C5 C 0.1772(3) 0.5986(3) 0.4227(5) 0.0262(9) Uani 1 1 d . . . . .
H5 H 0.1091 0.5776 0.4461 0.031 Uiso 1 1 calc R U . . .
C6 C 0.2639(3) 0.5409(3) 0.4602(5) 0.0252(9) Uani 1 1 d . . . . .
H6 H 0.2531 0.4814 0.5097 0.030 Uiso 1 1 calc R U . . .
C7 C 0.0983(3) 0.7532(3) 0.3263(5) 0.0233(9) Uani 1 1 d . . . . .
C8 C 0.1110(3) 0.8493(3) 0.3497(5) 0.0264(9) Uani 1 1 d . . . . .
H8 H 0.1787 0.8743 0.3763 0.032 Uiso 1 1 calc R U . . .
C9 C 0.0233(3) 0.9081(3) 0.3336(5) 0.0316(10) Uani 1 1 d . . . . .
H9 H 0.0325 0.9727 0.3466 0.038 Uiso 1 1 calc R U . . .
C10 C -0.0782(3) 0.8717(3) 0.2984(5) 0.0323(10) Uani 1 1 d . . . . .
H10 H -0.1370 0.9116 0.2911 0.039 Uiso 1 1 calc R U . . .
C11 C -0.0919(3) 0.7759(3) 0.2742(5) 0.0251(9) Uani 1 1 d . . . . .
C12 C -0.1984(3) 0.7313(3) 0.2354(6) 0.0322(10) Uani 1 1 d . . . . .
C13 C -0.0036(3) 0.7178(3) 0.2863(5) 0.0249(9) Uani 1 1 d . . . . .
H13 H -0.0126 0.6536 0.2672 0.030 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ni1 N1 2.014(3) . ?
Ni1 N1 2.014(3) 3_666 ?
Ni1 O1 2.023(2) . ?
Ni1 O1 2.023(2) 3_666 ?
Ni1 O5 2.119(2) 3_666 ?
Ni1 O5 2.119(2) . ?
N1 C6 1.332(4) . ?
N1 C2 1.351(4) . ?
O1 C1 1.254(4) . ?
O2 C1 1.242(4) . ?
O3 C12 1.317(4) . ?
O3 H3 0.8200 . ?
O4 C12 1.213(5) . ?
O5 H1W 0.8443 . ?
O5 H2W 0.6781 . ?
O6 H3W 0.8676 . ?
O6 H4W 0.8459 . ?
C1 C2 1.530(5) . ?
C2 C3 1.382(5) . ?
C3 C4 1.392(5) . ?
C3 H2 0.9300 . ?
C4 C5 1.391(5) . ?
C4 C7 1.488(5) . ?
C5 C6 1.377(5) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C8 1.386(5) . ?
C7 C13 1.388(5) . ?
C8 C9 1.382(5) . ?
C8 H8 0.9300 . ?
C9 C10 1.385(5) . ?
C9 H9 0.9300 . ?
C10 C11 1.383(5) . ?
C10 H10 0.9300 . ?
C11 C13 1.381(5) . ?
C11 C12 1.492(5) . ?
C13 H13 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 Ni1 N1 180.0 . 3_666 ?
N1 Ni1 O1 80.97(10) . . ?
N1 Ni1 O1 99.03(10) 3_666 . ?
N1 Ni1 O1 99.03(10) . 3_666 ?
N1 Ni1 O1 80.97(10) 3_666 3_666 ?
O1 Ni1 O1 180.0 . 3_666 ?
N1 Ni1 O5 88.74(11) . 3_666 ?
N1 Ni1 O5 91.26(11) 3_666 3_666 ?
O1 Ni1 O5 92.37(10) . 3_666 ?
O1 Ni1 O5 87.63(10) 3_666 3_666 ?
N1 Ni1 O5 91.26(11) . . ?
N1 Ni1 O5 88.74(11) 3_666 . ?
O1 Ni1 O5 87.63(10) . . ?
O1 Ni1 O5 92.37(10) 3_666 . ?
O5 Ni1 O5 180.0 3_666 . ?
C6 N1 C2 118.8(3) . . ?
C6 N1 Ni1 127.6(2) . . ?
C2 N1 Ni1 113.5(2) . . ?
C1 O1 Ni1 115.8(2) . . ?
C12 O3 H3 109.5 . . ?
Ni1 O5 H1W 109.7 . . ?
Ni1 O5 H2W 109.8 . . ?
H1W O5 H2W 112.5 . . ?
H3W O6 H4W 112.1 . . ?
O2 C1 O1 125.8(3) . . ?
O2 C1 C2 118.5(3) . . ?
O1 C1 C2 115.7(3) . . ?
N1 C2 C3 122.0(3) . . ?
N1 C2 C1 113.6(3) . . ?
C3 C2 C1 124.4(3) . . ?
C2 C3 C4 119.5(3) . . ?
C2 C3 H2 120.2 . . ?
C4 C3 H2 120.2 . . ?
C5 C4 C3 117.3(3) . . ?
C5 C4 C7 119.8(3) . . ?
C3 C4 C7 122.8(3) . . ?
C6 C5 C4 120.3(4) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
N1 C6 C5 122.0(4) . . ?
N1 C6 H6 119.0 . . ?
C5 C6 H6 119.0 . . ?
C8 C7 C13 118.7(4) . . ?
C8 C7 C4 121.0(3) . . ?
C13 C7 C4 120.3(3) . . ?
C9 C8 C7 120.1(4) . . ?
C9 C8 H8 120.0 . . ?
C7 C8 H8 120.0 . . ?
C8 C9 C10 120.6(4) . . ?
C8 C9 H9 119.7 . . ?
C10 C9 H9 119.7 . . ?
C11 C10 C9 119.8(4) . . ?
C11 C10 H10 120.1 . . ?
C9 C10 H10 120.1 . . ?
C13 C11 C10 119.2(4) . . ?
C13 C11 C12 117.7(4) . . ?
C10 C11 C12 123.1(4) . . ?
O4 C12 O3 124.7(4) . . ?
O4 C12 C11 122.3(4) . . ?
O3 C12 C11 112.9(4) . . ?
C11 C13 C7 121.5(4) . . ?
C11 C13 H13 119.3 . . ?
C7 C13 H13 119.3 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Ni1 O1 C1 O2 -175.4(3) . . . . ?
Ni1 O1 C1 C2 4.2(4) . . . . ?
C6 N1 C2 C3 2.9(5) . . . . ?
Ni1 N1 C2 C3 -172.6(3) . . . . ?
C6 N1 C2 C1 -177.8(3) . . . . ?
Ni1 N1 C2 C1 6.7(4) . . . . ?
O2 C1 C2 N1 172.3(3) . . . . ?
O1 C1 C2 N1 -7.4(4) . . . . ?
O2 C1 C2 C3 -8.5(5) . . . . ?
O1 C1 C2 C3 171.9(3) . . . . ?
N1 C2 C3 C4 -0.6(5) . . . . ?
C1 C2 C3 C4 -179.8(3) . . . . ?
C2 C3 C4 C5 -2.2(5) . . . . ?
C2 C3 C4 C7 174.9(3) . . . . ?
C3 C4 C5 C6 2.8(5) . . . . ?
C7 C4 C5 C6 -174.5(3) . . . . ?
C2 N1 C6 C5 -2.4(5) . . . . ?
Ni1 N1 C6 C5 172.4(3) . . . . ?
C4 C5 C6 N1 -0.5(6) . . . . ?
C5 C4 C7 C8 146.5(4) . . . . ?
C3 C4 C7 C8 -30.5(5) . . . . ?
C5 C4 C7 C13 -31.3(5) . . . . ?
C3 C4 C7 C13 151.6(3) . . . . ?
C13 C7 C8 C9 0.1(6) . . . . ?
C4 C7 C8 C9 -177.7(3) . . . . ?
C7 C8 C9 C10 1.5(6) . . . . ?
C8 C9 C10 C11 -1.7(6) . . . . ?
C9 C10 C11 C13 0.2(6) . . . . ?
C9 C10 C11 C12 -179.8(4) . . . . ?
C13 C11 C12 O4 -0.9(6) . . . . ?
C10 C11 C12 O4 179.2(4) . . . . ?
C13 C11 C12 O3 178.7(3) . . . . ?
C10 C11 C12 O3 -1.2(6) . . . . ?
C10 C11 C13 C7 1.4(6) . . . . ?
C12 C11 C13 C7 -178.5(3) . . . . ?
C8 C7 C13 C11 -1.6(6) . . . . ?
C4 C7 C13 C11 176.3(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O3 H3 O2 0.82 1.92 2.689(3) 155.8 1_455
O5 H1W O2 0.84 1.85 2.697(4) 179.5 2_645
O5 H2W O6 0.68 2.13 2.807(4) 173.4 1_554
O6 H3W O4 0.87 1.98 2.846(4) 177.0 3_566
O6 H4W O5 0.85 1.97 2.808(4) 172.7 3_666

_refine_diff_density_max         0.310
_refine_diff_density_min         -0.326
_refine_diff_density_rms         0.083

####################################################################### 
# 
# 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_compound_3
_database_code_depnum_ccdc_archive 'CCDC 1498140'
_audit_update_record             
;
2016-11-11 deposited with the CCDC.
2016-11-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
#_shelx_SHELXL_version_number      '2014/7'
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H11 N Ni O6'
_chemical_formula_weight         335.94

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'
Ni Ni 0.3393 1.1124 '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                   12.5405(4)
_cell_length_b                   13.8008(4)
_cell_length_c                   7.0319(3)
_cell_angle_alpha                90
_cell_angle_beta                 93.828(3)
_cell_angle_gamma                90
_cell_volume                     1214.29(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4412
_cell_measurement_theta_min      3.368
_cell_measurement_theta_max      25.049

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.838
_exptl_crystal_F_000             688
_exptl_transmission_factor_min   0.683
_exptl_transmission_factor_max   0.734
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.190
_exptl_absorpt_coefficient_mu    1.628
_shelx_estimated_absorpt_T_min   0.659
_shelx_estimated_absorpt_T_max   0.747
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
#_exptl_absorpt_special_details    ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APE-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4412
_diffrn_reflns_av_unetI/netI     0.0495
_diffrn_reflns_av_R_equivalents  0.0328
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         3.368
_diffrn_reflns_theta_max         25.049
_diffrn_reflns_theta_full        25.049
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             2161
_reflns_number_gt                1776
_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0299P)²+0.5389P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2161
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0475
_refine_ls_R_factor_gt           0.0352
_refine_ls_wR_factor_ref         0.0838
_refine_ls_wR_factor_gt          0.0753
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_restrained_S_all      1.065
_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
Ni1 Ni -0.27565(3) 0.61359(3) 0.49975(6) 0.01923(15) Uani 1 1 d . . . . .
O1 O -0.26949(16) 0.76290(14) 0.5463(3) 0.0235(5) Uani 1 1 d . . . . .
O2 O -0.18620(17) 0.86981(14) 0.7442(3) 0.0234(5) Uani 1 1 d . . . . .
O3 O 0.26344(16) 0.96989(14) 1.0249(3) 0.0232(5) Uani 1 1 d . . . . .
O4 O 0.42652(17) 0.93090(15) 1.1467(3) 0.0304(6) Uani 1 1 d . . . . .
O5 O -0.41262(18) 0.62142(15) 0.3262(3) 0.0346(6) Uani 1 1 d . . . . .
H1W H -0.4334 0.5573 0.3224 0.042 Uiso 1 1 d R U . . .
H2W H -0.4004 0.6375 0.2412 0.042 Uiso 1 1 d R U . . .
O6 O -0.36446(18) 0.60462(15) 0.7414(3) 0.0321(6) Uani 1 1 d . . . . .
H3W H -0.4301 0.5933 0.7113 0.038 Uiso 1 1 d R U . . .
H4W H -0.3421 0.6380 0.8289 0.038 Uiso 1 1 d R U . . .
N1 N -0.1354(2) 0.62228(16) 0.6609(4) 0.0186(6) Uani 1 1 d . . . . .
C1 C -0.1948(2) 0.7887(2) 0.6656(4) 0.0190(7) Uani 1 1 d . . . . .
C2 C -0.1101(2) 0.7128(2) 0.7188(4) 0.0166(6) Uani 1 1 d . . . . .
C3 C -0.0638(3) 0.5527(2) 0.7002(4) 0.0223(7) Uani 1 1 d . . . . .
H3 H -0.0813 0.4896 0.6642 0.027 Uiso 1 1 calc R U . . .
C4 C 0.0352(2) 0.5697(2) 0.7916(4) 0.0239(7) Uani 1 1 d . . . . .
H4 H 0.0832 0.5188 0.8122 0.029 Uiso 1 1 calc R U . . .
C5 C 0.0636(2) 0.6624(2) 0.8532(4) 0.0180(7) Uani 1 1 d . . . . .
C6 C -0.0142(2) 0.7346(2) 0.8161(4) 0.0180(7) Uani 1 1 d . . . . .
H6 H -0.0007 0.7976 0.8577 0.022 Uiso 1 1 calc R U . . .
C7 C 0.1700(2) 0.6849(2) 0.9483(4) 0.0178(7) Uani 1 1 d . . . . .
C8 C 0.2036(2) 0.7806(2) 0.9745(4) 0.0188(7) Uani 1 1 d . . . . .
H8 H 0.1568 0.8304 0.9375 0.023 Uiso 1 1 calc R U . . .
C9 C 0.3041(2) 0.8036(2) 1.0533(4) 0.0168(6) Uani 1 1 d . . . . .
C10 C 0.3350(2) 0.9087(2) 1.0774(4) 0.0174(7) Uani 1 1 d . . . . .
C11 C 0.3744(3) 0.7298(2) 1.1094(4) 0.0227(7) Uani 1 1 d . . . . .
H11A H 0.4423 0.7444 1.1626 0.027 Uiso 1 1 calc R U . . .
C12 C 0.3429(3) 0.6344(2) 1.0860(5) 0.0262(8) Uani 1 1 d . . . . .
H12A H 0.3901 0.5848 1.1227 0.031 Uiso 1 1 calc R U . . .
C13 C 0.2415(3) 0.6120(2) 1.0081(4) 0.0221(7) Uani 1 1 d . . . . .
H13 H 0.2209 0.5474 0.9956 0.027 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ni1 O3 1.997(2) 2_546 ?
Ni1 N1 2.031(3) . ?
Ni1 O5 2.042(2) . ?
Ni1 O1 2.087(2) . ?
Ni1 O6 2.096(2) . ?
Ni1 O2 2.193(2) 4_575 ?
O1 C1 1.266(3) . ?
O2 C1 1.250(3) . ?
O2 Ni1 2.193(2) 4_576 ?
O3 C10 1.270(3) . ?
O3 Ni1 1.997(2) 2_556 ?
O4 C10 1.254(4) . ?
O5 H1W 0.9228 . ?
O5 H2W 0.6649 . ?
O6 H3W 0.8506 . ?
O6 H4W 0.8043 . ?
N1 C3 1.331(4) . ?
N1 C2 1.346(4) . ?
C1 C2 1.520(4) . ?
C2 C6 1.376(4) . ?
C3 C4 1.379(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.390(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.407(4) . ?
C5 C7 1.484(4) . ?
C6 H6 0.9300 . ?
C7 C13 1.394(4) . ?
C7 C8 1.395(4) . ?
C8 C9 1.379(4) . ?
C8 H8 0.9300 . ?
C9 C11 1.388(4) . ?
C9 C10 1.508(4) . ?
C11 C12 1.381(4) . ?
C11 H11A 0.9300 . ?
C12 C13 1.385(4) . ?
C12 H12A 0.9300 . ?
C13 H13 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O3 Ni1 N1 92.21(9) 2_546 . ?
O3 Ni1 O5 93.84(8) 2_546 . ?
N1 Ni1 O5 173.01(9) . . ?
O3 Ni1 O1 172.57(8) 2_546 . ?
N1 Ni1 O1 80.36(8) . . ?
O5 Ni1 O1 93.57(8) . . ?
O3 Ni1 O6 93.42(9) 2_546 . ?
N1 Ni1 O6 92.21(10) . . ?
O5 Ni1 O6 90.93(10) . . ?
O1 Ni1 O6 86.98(8) . . ?
O3 Ni1 O2 89.21(8) 2_546 4_575 ?
N1 Ni1 O2 88.83(9) . 4_575 ?
O5 Ni1 O2 87.74(9) . 4_575 ?
O1 Ni1 O2 90.56(8) . 4_575 ?
O6 Ni1 O2 177.12(8) . 4_575 ?
C1 O1 Ni1 113.54(18) . . ?
C1 O2 Ni1 114.96(19) . 4_576 ?
C10 O3 Ni1 128.97(19) . 2_556 ?
Ni1 O5 H1W 101.0 . . ?
Ni1 O5 H2W 108.6 . . ?
H1W O5 H2W 112.1 . . ?
Ni1 O6 H3W 111.5 . . ?
Ni1 O6 H4W 114.1 . . ?
H3W O6 H4W 125.3 . . ?
C3 N1 C2 117.7(3) . . ?
C3 N1 Ni1 128.3(2) . . ?
C2 N1 Ni1 113.68(19) . . ?
O2 C1 O1 125.6(3) . . ?
O2 C1 C2 118.0(3) . . ?
O1 C1 C2 116.3(3) . . ?
N1 C2 C6 122.2(3) . . ?
N1 C2 C1 114.7(3) . . ?
C6 C2 C1 123.0(3) . . ?
N1 C3 C4 123.2(3) . . ?
N1 C3 H3 118.4 . . ?
C4 C3 H3 118.4 . . ?
C3 C4 C5 120.4(3) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C4 C5 C6 115.7(3) . . ?
C4 C5 C7 122.5(3) . . ?
C6 C5 C7 121.8(3) . . ?
C2 C6 C5 120.7(3) . . ?
C2 C6 H6 119.7 . . ?
C5 C6 H6 119.7 . . ?
C13 C7 C8 117.4(3) . . ?
C13 C7 C5 121.7(3) . . ?
C8 C7 C5 120.8(3) . . ?
C9 C8 C7 122.1(3) . . ?
C9 C8 H8 118.9 . . ?
C7 C8 H8 118.9 . . ?
C8 C9 C11 119.4(3) . . ?
C8 C9 C10 119.3(3) . . ?
C11 C9 C10 121.4(3) . . ?
O4 C10 O3 124.1(3) . . ?
O4 C10 C9 120.1(3) . . ?
O3 C10 C9 115.8(3) . . ?
C12 C11 C9 119.7(3) . . ?
C12 C11 H11A 120.2 . . ?
C9 C11 H11A 120.2 . . ?
C11 C12 C13 120.5(3) . . ?
C11 C12 H12A 119.8 . . ?
C13 C12 H12A 119.8 . . ?
C12 C13 C7 120.9(3) . . ?
C12 C13 H13 119.5 . . ?
C7 C13 H13 119.5 . . ?

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
Ni1 O2 C1 O1 84.6(3) 4_576 . . . ?
Ni1 O2 C1 C2 -94.3(3) 4_576 . . . ?
Ni1 O1 C1 O2 -165.8(2) . . . . ?
Ni1 O1 C1 C2 13.1(3) . . . . ?
C3 N1 C2 C6 -0.2(4) . . . . ?
Ni1 N1 C2 C6 -174.6(2) . . . . ?
C3 N1 C2 C1 178.9(3) . . . . ?
Ni1 N1 C2 C1 4.5(3) . . . . ?
O2 C1 C2 N1 166.8(3) . . . . ?
O1 C1 C2 N1 -12.1(4) . . . . ?
O2 C1 C2 C6 -14.1(4) . . . . ?
O1 C1 C2 C6 167.0(3) . . . . ?
C2 N1 C3 C4 -1.9(5) . . . . ?
Ni1 N1 C3 C4 171.6(2) . . . . ?
N1 C3 C4 C5 2.0(5) . . . . ?
C3 C4 C5 C6 0.1(4) . . . . ?
C3 C4 C5 C7 -178.6(3) . . . . ?
N1 C2 C6 C5 2.3(4) . . . . ?
C1 C2 C6 C5 -176.8(3) . . . . ?
C4 C5 C6 C2 -2.1(4) . . . . ?
C7 C5 C6 C2 176.6(3) . . . . ?
C4 C5 C7 C13 -10.2(4) . . . . ?
C6 C5 C7 C13 171.2(3) . . . . ?
C4 C5 C7 C8 167.3(3) . . . . ?
C6 C5 C7 C8 -11.3(4) . . . . ?
C13 C7 C8 C9 1.0(4) . . . . ?
C5 C7 C8 C9 -176.6(3) . . . . ?
C7 C8 C9 C11 -0.2(4) . . . . ?
C7 C8 C9 C10 180.0(3) . . . . ?
Ni1 O3 C10 O4 9.1(4) 2_556 . . . ?
Ni1 O3 C10 C9 -171.35(18) 2_556 . . . ?
C8 C9 C10 O4 -179.1(3) . . . . ?
C11 C9 C10 O4 1.1(4) . . . . ?
C8 C9 C10 O3 1.3(4) . . . . ?
C11 C9 C10 O3 -178.5(3) . . . . ?
C8 C9 C11 C12 -0.1(4) . . . . ?
C10 C9 C11 C12 179.7(3) . . . . ?
C9 C11 C12 C13 -0.4(5) . . . . ?
C11 C12 C13 C7 1.3(5) . . . . ?
C8 C7 C13 C12 -1.6(4) . . . . ?
C5 C7 C13 C12 176.0(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O6 H3W O4 0.85 1.86 2.706(3) 179.7 4_475
C3 H3 O3 0.93 2.58 3.091(4) 115.1 2_546
C4 H4 O2 0.93 2.47 3.365(4) 160.4 2_546
O6 H4W O1 0.80 2.20 3.003(3) 173.7 4_576
O5 H1W O3 0.92 2.62 2.951(3) 102.1 2_546
O5 H1W O4 0.92 1.76 2.643(3) 159.5 2_546
O5 H2W O1 0.66 2.60 3.181(3) 147.3 4_575

_refine_diff_density_max         0.331
_refine_diff_density_min         -0.347
_refine_diff_density_rms         0.083

####################################################################### 
# 
# 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_compound_2
_database_code_depnum_ccdc_archive 'CCDC 1505548'
_audit_update_record             
;
2016-11-11 deposited with the CCDC.
2016-11-21 downloaded from the CCDC.
;
_audit_creation_date             2016-11-09
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C26 H20 N2 O10 Zn, 2(H2 O)'
_chemical_formula_sum            'C26 H24 N2 O12 Zn'
_chemical_formula_weight         621.84
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   12.523(4)
_cell_length_b                   14.220(3)
_cell_length_c                   7.0884(19)
_cell_angle_alpha                90
_cell_angle_beta                 93.40(4)
_cell_angle_gamma                90
_cell_volume                     1260.1(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    359
_cell_measurement_temperature    295.69(16)
_cell_measurement_theta_max      26.4900
_cell_measurement_theta_min      4.3260
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.048
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91636
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
#_exptl_absorpt_special_details    ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.639
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.21
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_av_unetI/netI     0.1183
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            3635
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.500
_diffrn_reflns_theta_max         26.020
_diffrn_reflns_theta_min         3.259
_diffrn_ambient_temperature      295.69(16)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -16.00   89.60   1.2000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       27.0108   38.0000  -90.0000 88

#__ type_ start__ end____ width___ exp.time_
  2 omega  -13.00   24.20   1.2000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      -24.0420  -99.0000 -120.0000 31

#__ type_ start__ end____ width___ exp.time_
  3 omega  -86.00  -50.00   1.2000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      -24.0420  -57.0000    0.0000 30

#__ type_ start__ end____ width___ exp.time_
  4 omega   35.00  110.60   1.2000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       27.0108  178.0000  150.0000 63
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0102741000
_diffrn_orient_matrix_UB_12      -0.0483346000
_diffrn_orient_matrix_UB_13      0.0163525000
_diffrn_orient_matrix_UB_21      -0.0553442000
_diffrn_orient_matrix_UB_22      0.0099537000
_diffrn_orient_matrix_UB_23      0.0031027000
_diffrn_orient_matrix_UB_31      -0.0067855000
_diffrn_orient_matrix_UB_32      -0.0076769000
_diffrn_orient_matrix_UB_33      -0.0988506000
loop_
# _diffrn_oxdiff_twin_id
#_diffrn_oxdiff_twin_ratio
#_diffrn_oxdiff_twin_reflns_isolated
#_diffrn_oxdiff_twin_reflns_overlapped
#1 0.4387 1814 3168
#2 0.5613 1825 3168

_diffrn_radiation_monochromator
mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2190
_reflns_number_total             3635
_reflns_special_details          
;
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.675
_refine_diff_density_min         -0.774
_refine_diff_density_rms         0.110
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.927
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     197
_refine_ls_number_reflns         3635
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.1023
_refine_ls_R_factor_gt           0.0561
_refine_ls_restrained_S_all      0.928
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0575P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1206
_refine_ls_wR_factor_ref         0.1319
_refine_special_details          
;
 Refined as a 2-component twin.

_olex2_refinement_description

1. Twinned data refinement
 Scales: 0.4328(17) 0.5672(17)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups, All O(H,H) groups
3. Restrained distances
 H5B-O5
 0.86 with sigma of 0.01
 O5-H5A
 0.86 with sigma of 0.01
 H5B-H5A
 1.48 with sigma of 0.01
 H6B-H5A
 2.32 with sigma of 0.02
4.a Free rotating group:
 O6(H6A,H6B)
4.b Rotating group:
 O5(H5A)
4.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C6(H6), C8(H8), C10(H10), C11(H11), C12(H12)
4.d Idealised tetrahedral OH refined as rotating group:
 O4(H4)

;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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 0.5000 0.5000 0.5000 0.0247(3) Uani 1 2 d S T P . .
O1 O 0.4392(3) 0.3850(2) 0.6236(5) 0.0209(8) Uani 1 1 d . . . . .
O2 O 0.4853(2) 0.2543(3) 0.7782(5) 0.0256(9) Uani 1 1 d . . . . .
O3 O 1.2090(3) 0.3526(3) 0.7885(6) 0.0407(12) Uani 1 1 d . . . . .
O4 O 1.2778(3) 0.2081(3) 0.7721(6) 0.0417(12) Uani 1 1 d . . . . .
H4 H 1.3351 0.2359 0.7861 0.063 Uiso 1 1 calc GR . . . .
O5 O 0.5022(3) 0.5657(3) 0.7673(5) 0.0274(8) Uani 1 1 d D . . . .
H5A H 0.5552 0.5441 0.8419 0.041 Uiso 1 1 d DGR . . . .
N1 N 0.6376(3) 0.4323(3) 0.5729(5) 0.0175(10) Uani 1 1 d . . . . .
C1 C 0.5064(4) 0.3265(3) 0.6852(6) 0.0169(11) Uani 1 1 d . . . . .
C2 C 0.6223(4) 0.3464(3) 0.6505(7) 0.0144(11) Uani 1 1 d . . . . .
C3 C 0.7058(4) 0.2857(3) 0.6898(7) 0.0171(12) Uani 1 1 d . . . . .
H3 H 0.6937 0.2272 0.7431 0.020 Uiso 1 1 calc R . . . .
C4 C 0.8082(4) 0.3124(4) 0.6493(7) 0.0174(12) Uani 1 1 d . . . . .
C5 C 0.8223(4) 0.4013(4) 0.5764(7) 0.0200(12) Uani 1 1 d . . . . .
H5 H 0.8905 0.4219 0.5515 0.024 Uiso 1 1 calc R . . . .
C6 C 0.7357(4) 0.4593(4) 0.5406(7) 0.0208(12) Uani 1 1 d . . . . .
H6 H 0.7466 0.5192 0.4924 0.025 Uiso 1 1 calc R . . . .
C7 C 0.9013(4) 0.2464(4) 0.6733(8) 0.0185(12) Uani 1 1 d . . . . .
C8 C 1.0032(4) 0.2816(4) 0.7142(8) 0.0217(14) Uani 1 1 d . . . . .
H8 H 1.0120 0.3459 0.7332 0.026 Uiso 1 1 calc R . . . .
C9 C 1.0917(4) 0.2241(4) 0.7274(8) 0.0240(14) Uani 1 1 d . . . . .
C10 C 1.0773(4) 0.1279(4) 0.7014(8) 0.0283(14) Uani 1 1 d . . . . .
H10 H 1.1363 0.0880 0.7079 0.034 Uiso 1 1 calc R . . . .
C11 C 0.9775(4) 0.0917(4) 0.6664(8) 0.0249(14) Uani 1 1 d . . . . .
H11 H 0.9688 0.0271 0.6530 0.030 Uiso 1 1 calc R . . . .
C12 C 0.8888(4) 0.1501(4) 0.6506(7) 0.0227(13) Uani 1 1 d . . . . .
H12 H 0.8210 0.1248 0.6249 0.027 Uiso 1 1 calc R . . . .
C13 C 1.1993(4) 0.2692(4) 0.7648(8) 0.0287(15) Uani 1 1 d . . . . .
O6 O 0.3365(3) 0.4945(3) 0.9730(6) 0.0395(10) Uani 1 1 d . . . . .
H6A H 0.3093 0.4441 0.9268 0.059 Uiso 1 1 d G . . . .
H6B H 0.3791 0.5177 0.8965 0.059 Uiso 1 1 d DG . . . .
H5B H 0.500(4) 0.6245(11) 0.747(7) 0.05(2) 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
Zn1 O1 2.024(3) . ?
Zn1 O1 2.025(3) 3_666 ?
Zn1 O5 2.111(3) . ?
Zn1 O5 2.111(3) 3_666 ?
Zn1 N1 2.014(4) 3_666 ?
Zn1 N1 2.014(4) . ?
O1 C1 1.244(5) . ?
O2 C1 1.257(5) . ?
O3 C13 1.203(6) . ?
O4 H4 0.8200 . ?
O4 C13 1.311(6) . ?
O5 H5A 0.8793 . ?
O5 H5B 0.849(12) . ?
N1 C2 1.358(6) . ?
N1 C6 1.321(6) . ?
C1 C2 1.514(7) . ?
C2 C3 1.372(6) . ?
C3 H3 0.9300 . ?
C3 C4 1.383(6) . ?
C4 C5 1.381(7) . ?
C4 C7 1.499(7) . ?
C5 H5 0.9300 . ?
C5 C6 1.374(7) . ?
C6 H6 0.9300 . ?
C7 C8 1.384(6) . ?
C7 C12 1.386(7) . ?
C8 H8 0.9300 . ?
C8 C9 1.377(6) . ?
C9 C10 1.391(7) . ?
C9 C13 1.501(7) . ?
C10 H10 0.9300 . ?
C10 C11 1.360(7) . ?
C11 H11 0.9300 . ?
C11 C12 1.387(7) . ?
C12 H12 0.9300 . ?
O6 H6A 0.8504 . ?
O6 H6B 0.8498 . ?

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 O1 180.00(18) . 3_666 ?
O1 Zn1 O5 92.61(15) 3_666 . ?
O1 Zn1 O5 87.39(15) . . ?
O1 Zn1 O5 87.38(15) 3_666 3_666 ?
O1 Zn1 O5 92.61(15) . 3_666 ?
O5 Zn1 O5 180.0 3_666 . ?
N1 Zn1 O1 99.16(14) 3_666 . ?
N1 Zn1 O1 80.84(14) . . ?
N1 Zn1 O1 99.16(14) . 3_666 ?
N1 Zn1 O1 80.84(14) 3_666 3_666 ?
N1 Zn1 O5 89.11(15) 3_666 . ?
N1 Zn1 O5 90.89(15) . . ?
N1 Zn1 O5 90.89(15) 3_666 3_666 ?
N1 Zn1 O5 89.11(15) . 3_666 ?
N1 Zn1 N1 180.0 . 3_666 ?
C1 O1 Zn1 115.4(3) . . ?
C13 O4 H4 109.5 . . ?
Zn1 O5 H5A 110.8 . . ?
Zn1 O5 H5B 106(4) . . ?
H5A O5 H5B 117.4 . . ?
C2 N1 Zn1 113.3(3) . . ?
C6 N1 Zn1 127.4(3) . . ?
C6 N1 C2 119.1(4) . . ?
O1 C1 O2 124.9(5) . . ?
O1 C1 C2 116.9(4) . . ?
O2 C1 C2 118.1(4) . . ?
N1 C2 C1 113.2(4) . . ?
N1 C2 C3 121.6(5) . . ?
C3 C2 C1 125.2(5) . . ?
C2 C3 H3 120.3 . . ?
C2 C3 C4 119.3(5) . . ?
C4 C3 H3 120.3 . . ?
C3 C4 C7 122.0(5) . . ?
C5 C4 C3 118.0(5) . . ?
C5 C4 C7 120.0(5) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 C4 120.1(5) . . ?
C6 C5 H5 119.9 . . ?
N1 C6 C5 121.7(5) . . ?
N1 C6 H6 119.1 . . ?
C5 C6 H6 119.1 . . ?
C8 C7 C4 119.9(5) . . ?
C8 C7 C12 118.6(5) . . ?
C12 C7 C4 121.5(5) . . ?
C7 C8 H8 119.1 . . ?
C9 C8 C7 121.8(5) . . ?
C9 C8 H8 119.1 . . ?
C8 C9 C10 118.5(5) . . ?
C8 C9 C13 118.0(5) . . ?
C10 C9 C13 123.4(5) . . ?
C9 C10 H10 119.8 . . ?
C11 C10 C9 120.4(5) . . ?
C11 C10 H10 119.8 . . ?
C10 C11 H11 119.6 . . ?
C10 C11 C12 120.8(5) . . ?
C12 C11 H11 119.6 . . ?
C7 C12 H12 120.1 . . ?
C11 C12 C7 119.8(5) . . ?
C11 C12 H12 120.1 . . ?
O3 C13 O4 125.4(6) . . ?
O3 C13 C9 121.8(5) . . ?
O4 C13 C9 112.8(5) . . ?
H6A O6 H6B 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O4 H4 O2 0.82 1.90 2.678(5) 157.2 1_655

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
Zn1 O1 C1 O2 174.6(4) . . . . ?
Zn1 O1 C1 C2 -3.2(5) . . . . ?
Zn1 N1 C2 C1 -6.8(5) . . . . ?
Zn1 N1 C2 C3 172.7(4) . . . . ?
Zn1 N1 C6 C5 -171.7(4) . . . . ?
O1 C1 C2 N1 6.8(6) . . . . ?
O1 C1 C2 C3 -172.7(5) . . . . ?
O2 C1 C2 N1 -171.1(4) . . . . ?
O2 C1 C2 C3 9.4(7) . . . . ?
N1 C2 C3 C4 -0.1(7) . . . . ?
C1 C2 C3 C4 179.4(4) . . . . ?
C2 N1 C6 C5 2.6(7) . . . . ?
C2 C3 C4 C5 2.2(7) . . . . ?
C2 C3 C4 C7 -174.7(5) . . . . ?
C3 C4 C5 C6 -2.0(7) . . . . ?
C3 C4 C7 C8 -151.4(5) . . . . ?
C3 C4 C7 C12 30.4(8) . . . . ?
C4 C5 C6 N1 -0.5(8) . . . . ?
C4 C7 C8 C9 -176.5(5) . . . . ?
C4 C7 C12 C11 177.4(5) . . . . ?
C5 C4 C7 C8 31.8(8) . . . . ?
C5 C4 C7 C12 -146.5(5) . . . . ?
C6 N1 C2 C1 178.1(4) . . . . ?
C6 N1 C2 C3 -2.4(7) . . . . ?
C7 C4 C5 C6 175.0(5) . . . . ?
C7 C8 C9 C10 -0.9(9) . . . . ?
C7 C8 C9 C13 177.7(5) . . . . ?
C8 C7 C12 C11 -0.9(8) . . . . ?
C8 C9 C10 C11 -0.9(9) . . . . ?
C8 C9 C13 O3 2.2(8) . . . . ?
C8 C9 C13 O4 -179.2(5) . . . . ?
C9 C10 C11 C12 1.9(9) . . . . ?
C10 C9 C13 O3 -179.2(6) . . . . ?
C10 C9 C13 O4 -0.6(8) . . . . ?
C10 C11 C12 C7 -0.9(9) . . . . ?
C12 C7 C8 C9 1.9(9) . . . . ?
C13 C9 C10 C11 -179.5(5) . . . . ?

#_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.4328(17)
2 0.5672(17)

####################################################################### 
# 
# 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_compound_6
_database_code_depnum_ccdc_archive 'CCDC 1505549'
_audit_update_record             
;
2016-11-11 deposited with the CCDC.
2016-11-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
#_shelx_SHELXL_version_number      '2014/7'
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H15 N3 O4 Zn'
_chemical_formula_weight         462.75

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/n'
_space_group_name_Hall           '-P 2yn'

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

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

_cell_length_a                   9.0764(14)
_cell_length_b                   16.0794(16)
_cell_length_c                   13.913(3)
_cell_angle_alpha                90
_cell_angle_beta                 106.70(2)
_cell_angle_gamma                90
_cell_volume                     1944.9(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    7322
_cell_measurement_theta_min      3.309
_cell_measurement_theta_max      25.050

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.580
_exptl_crystal_F_000             944
_exptl_transmission_factor_min   0.702
_exptl_transmission_factor_max   0.723
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.260
_exptl_crystal_size_min          0.250
_exptl_absorpt_coefficient_mu    1.300
_shelx_estimated_absorpt_T_min   0.712
_shelx_estimated_absorpt_T_max   0.737
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
#_exptl_absorpt_special_details    ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APE-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7322
_diffrn_reflns_av_unetI/netI     0.1678
_diffrn_reflns_av_R_equivalents  0.1007
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.309
_diffrn_reflns_theta_max         25.050
_diffrn_reflns_theta_full        25.050
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3429
_reflns_number_gt                1730
_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0047P)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         3429
_refine_ls_number_parameters     280
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1595
_refine_ls_R_factor_gt           0.0684
_refine_ls_wR_factor_ref         0.1034
_refine_ls_wR_factor_gt          0.0781
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_restrained_S_all      1.003
_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 0.64732(8) 0.38360(4) 0.86890(7) 0.0389(2) Uani 1 1 d . . . . .
N1 N 0.5662(6) 0.2643(3) 0.8927(5) 0.0375(14) Uani 1 1 d . . . . .
N2 N 0.7449(6) 0.5051(3) 0.8767(4) 0.0441(15) Uani 1 1 d . . . . .
N3 N 0.8635(6) 0.3615(3) 0.8527(4) 0.0432(15) Uani 1 1 d . . . . .
O1 O 0.6663(4) 0.3874(2) 1.0177(3) 0.0467(12) Uani 1 1 d . . . . .
O2 O 0.6593(6) 0.3106(3) 1.1487(4) 0.0742(17) Uani 1 1 d . . . . .
O3 O -0.0540(5) -0.1552(3) 0.8379(4) 0.0629(16) Uani 1 1 d . . . . .
O4 O 0.0380(5) -0.0787(2) 0.7349(4) 0.0484(13) Uani 1 1 d . . . . .
C1 C 0.6369(8) 0.3218(4) 1.0607(6) 0.046(2) Uani 1 1 d . . . . .
C2 C 0.5649(7) 0.2519(4) 0.9874(6) 0.0376(17) Uani 1 1 d . . . . .
C3 C 0.4942(7) 0.2095(4) 0.8232(5) 0.0460(19) Uani 1 1 d . . . . .
H3 H 0.4962 0.2168 0.7573 0.055 Uiso 1 1 calc R U . . .
C4 C 0.4169(7) 0.1423(4) 0.8465(6) 0.047(2) Uani 1 1 d . . . . .
H4 H 0.3663 0.1060 0.7957 0.057 Uiso 1 1 calc R U . . .
C5 C 0.4128(7) 0.1275(4) 0.9434(5) 0.0348(17) Uani 1 1 d . . . . .
C6 C 0.4936(7) 0.1837(4) 1.0159(5) 0.0398(18) Uani 1 1 d . . . . .
H6 H 0.4996 0.1754 1.0831 0.048 Uiso 1 1 calc R U . . .
C7 C 0.3241(7) 0.0570(4) 0.9679(6) 0.0340(17) Uani 1 1 d . . . . .
C8 C 0.3259(8) 0.0378(4) 1.0649(6) 0.050(2) Uani 1 1 d . . . . .
H8 H 0.3864 0.0690 1.1180 0.060 Uiso 1 1 calc R U . . .
C9 C 0.2387(8) -0.0275(4) 1.0843(6) 0.059(2) Uani 1 1 d . . . . .
H9 H 0.2432 -0.0405 1.1502 0.070 Uiso 1 1 calc R U . . .
C10 C 0.1455(7) -0.0732(4) 1.0068(6) 0.047(2) Uani 1 1 d . . . . .
H10 H 0.0864 -0.1164 1.0204 0.057 Uiso 1 1 calc R U . . .
C11 C 0.1398(7) -0.0552(4) 0.9096(6) 0.0381(18) Uani 1 1 d . . . . .
C12 C 0.0327(8) -0.1008(4) 0.8222(6) 0.0450(19) Uani 1 1 d . . . . .
C13 C 0.2290(7) 0.0107(3) 0.8905(5) 0.0397(18) Uani 1 1 d . . . . .
H13 H 0.2242 0.0236 0.8245 0.048 Uiso 1 1 calc R U . . .
C14 C 0.6735(8) 0.5756(4) 0.8872(6) 0.062(2) Uani 1 1 d . . . . .
H14 H 0.5713 0.5726 0.8876 0.075 Uiso 1 1 calc R U . . .
C15 C 0.7422(11) 0.6518(5) 0.8974(6) 0.075(3) Uani 1 1 d . . . . .
H15 H 0.6890 0.7000 0.9037 0.090 Uiso 1 1 calc R U . . .
C16 C 0.8931(11) 0.6540(5) 0.8980(6) 0.070(3) Uani 1 1 d . . . . .
H16 H 0.9446 0.7047 0.9070 0.084 Uiso 1 1 calc R U . . .
C17 C 0.9709(8) 0.5829(5) 0.8856(6) 0.061(2) Uani 1 1 d . . . . .
H17 H 1.0728 0.5851 0.8844 0.073 Uiso 1 1 calc R U . . .
C18 C 0.8919(8) 0.5084(4) 0.8750(5) 0.0428(18) Uani 1 1 d . . . . .
C19 C 0.9579(7) 0.4271(4) 0.8577(5) 0.0399(18) Uani 1 1 d . . . . .
C20 C 1.1038(8) 0.4201(5) 0.8458(6) 0.068(2) Uani 1 1 d . . . . .
H20 H 1.1674 0.4662 0.8508 0.081 Uiso 1 1 calc R U . . .
C21 C 1.1512(9) 0.3420(7) 0.8261(7) 0.083(3) Uani 1 1 d . . . . .
H21 H 1.2483 0.3349 0.8175 0.100 Uiso 1 1 calc R U . . .
C22 C 1.0567(10) 0.2754(6) 0.8193(6) 0.076(3) Uani 1 1 d . . . . .
H22 H 1.0875 0.2228 0.8051 0.091 Uiso 1 1 calc R U . . .
C23 C 0.9156(8) 0.2872(4) 0.8337(6) 0.058(2) Uani 1 1 d . . . . .
H23 H 0.8522 0.2411 0.8301 0.070 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Zn1 O4 1.972(4) 2_556 ?
Zn1 O1 2.029(4) . ?
Zn1 N3 2.069(5) . ?
Zn1 N1 2.114(5) . ?
Zn1 N2 2.135(5) . ?
N1 C3 1.333(7) . ?
N1 C2 1.336(8) . ?
N2 C14 1.336(7) . ?
N2 C18 1.342(7) . ?
N3 C23 1.340(7) . ?
N3 C19 1.348(7) . ?
O1 C1 1.278(7) . ?
O2 C1 1.196(8) . ?
O3 C12 1.238(7) . ?
O4 C12 1.280(8) . ?
O4 Zn1 1.972(4) 2_546 ?
C1 C2 1.532(9) . ?
C2 C6 1.388(8) . ?
C3 C4 1.376(7) . ?
C3 H3 0.9300 . ?
C4 C5 1.380(8) . ?
C4 H4 0.9300 . ?
C5 C6 1.395(8) . ?
C5 C7 1.485(8) . ?
C6 H6 0.9300 . ?
C7 C8 1.380(9) . ?
C7 C13 1.387(8) . ?
C8 C9 1.388(8) . ?
C8 H8 0.9300 . ?
C9 C10 1.376(9) . ?
C9 H9 0.9300 . ?
C10 C11 1.369(9) . ?
C10 H10 0.9300 . ?
C11 C13 1.405(8) . ?
C11 C12 1.511(9) . ?
C13 H13 0.9300 . ?
C14 C15 1.364(8) . ?
C14 H14 0.9300 . ?
C15 C16 1.368(9) . ?
C15 H15 0.9300 . ?
C16 C17 1.380(9) . ?
C16 H16 0.9300 . ?
C17 C18 1.382(8) . ?
C17 H17 0.9300 . ?
C18 C19 1.486(8) . ?
C19 C20 1.386(8) . ?
C20 C21 1.380(9) . ?
C20 H20 0.9300 . ?
C21 C22 1.358(9) . ?
C21 H21 0.9300 . ?
C22 C23 1.365(9) . ?
C22 H22 0.9300 . ?
C23 H23 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O4 Zn1 O1 122.87(19) 2_556 . ?
O4 Zn1 N3 127.5(2) 2_556 . ?
O1 Zn1 N3 108.13(19) . . ?
O4 Zn1 N1 97.57(19) 2_556 . ?
O1 Zn1 N1 78.4(2) . . ?
N3 Zn1 N1 104.2(2) . . ?
O4 Zn1 N2 90.57(19) 2_556 . ?
O1 Zn1 N2 90.49(19) . . ?
N3 Zn1 N2 76.7(2) . . ?
N1 Zn1 N2 168.6(2) . . ?
C3 N1 C2 118.4(6) . . ?
C3 N1 Zn1 127.3(5) . . ?
C2 N1 Zn1 113.1(4) . . ?
C14 N2 C18 119.0(6) . . ?
C14 N2 Zn1 125.1(5) . . ?
C18 N2 Zn1 115.9(4) . . ?
C23 N3 C19 117.0(6) . . ?
C23 N3 Zn1 125.0(5) . . ?
C19 N3 Zn1 118.0(4) . . ?
C1 O1 Zn1 119.0(4) . . ?
C12 O4 Zn1 110.6(4) . 2_546 ?
O2 C1 O1 127.3(7) . . ?
O2 C1 C2 119.1(6) . . ?
O1 C1 C2 113.6(7) . . ?
N1 C2 C6 122.5(6) . . ?
N1 C2 C1 115.0(6) . . ?
C6 C2 C1 122.3(7) . . ?
N1 C3 C4 121.7(7) . . ?
N1 C3 H3 119.2 . . ?
C4 C3 H3 119.2 . . ?
C3 C4 C5 121.6(7) . . ?
C3 C4 H4 119.2 . . ?
C5 C4 H4 119.2 . . ?
C4 C5 C6 116.0(6) . . ?
C4 C5 C7 121.7(6) . . ?
C6 C5 C7 122.3(6) . . ?
C2 C6 C5 119.8(6) . . ?
C2 C6 H6 120.1 . . ?
C5 C6 H6 120.1 . . ?
C8 C7 C13 118.0(6) . . ?
C8 C7 C5 122.7(6) . . ?
C13 C7 C5 119.2(6) . . ?
C7 C8 C9 120.8(7) . . ?
C7 C8 H8 119.6 . . ?
C9 C8 H8 119.6 . . ?
C10 C9 C8 120.6(7) . . ?
C10 C9 H9 119.7 . . ?
C8 C9 H9 119.7 . . ?
C11 C10 C9 120.1(7) . . ?
C11 C10 H10 120.0 . . ?
C9 C10 H10 120.0 . . ?
C10 C11 C13 119.1(7) . . ?
C10 C11 C12 121.7(7) . . ?
C13 C11 C12 119.1(7) . . ?
O3 C12 O4 124.4(7) . . ?
O3 C12 C11 119.7(8) . . ?
O4 C12 C11 116.0(7) . . ?
C7 C13 C11 121.5(7) . . ?
C7 C13 H13 119.3 . . ?
C11 C13 H13 119.3 . . ?
N2 C14 C15 123.5(7) . . ?
N2 C14 H14 118.2 . . ?
C15 C14 H14 118.2 . . ?
C14 C15 C16 116.8(7) . . ?
C14 C15 H15 121.6 . . ?
C16 C15 H15 121.6 . . ?
C15 C16 C17 121.7(7) . . ?
C15 C16 H16 119.1 . . ?
C17 C16 H16 119.1 . . ?
C16 C17 C18 117.5(7) . . ?
C16 C17 H17 121.2 . . ?
C18 C17 H17 121.2 . . ?
N2 C18 C17 121.4(6) . . ?
N2 C18 C19 114.6(6) . . ?
C17 C18 C19 124.0(7) . . ?
N3 C19 C20 123.0(6) . . ?
N3 C19 C18 114.7(6) . . ?
C20 C19 C18 122.3(7) . . ?
C21 C20 C19 117.4(7) . . ?
C21 C20 H20 121.3 . . ?
C19 C20 H20 121.3 . . ?
C22 C21 C20 120.3(8) . . ?
C22 C21 H21 119.8 . . ?
C20 C21 H21 119.8 . . ?
C21 C22 C23 118.7(8) . . ?
C21 C22 H22 120.6 . . ?
C23 C22 H22 120.6 . . ?
N3 C23 C22 123.5(7) . . ?
N3 C23 H23 118.3 . . ?
C22 C23 H23 118.3 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Zn1 O1 C1 O2 170.7(7) . . . . ?
Zn1 O1 C1 C2 -9.4(7) . . . . ?
C3 N1 C2 C6 0.9(10) . . . . ?
Zn1 N1 C2 C6 169.4(5) . . . . ?
C3 N1 C2 C1 -174.5(5) . . . . ?
Zn1 N1 C2 C1 -6.0(7) . . . . ?
O2 C1 C2 N1 -169.9(7) . . . . ?
O1 C1 C2 N1 10.2(8) . . . . ?
O2 C1 C2 C6 14.6(11) . . . . ?
O1 C1 C2 C6 -165.3(6) . . . . ?
C2 N1 C3 C4 1.4(9) . . . . ?
Zn1 N1 C3 C4 -165.2(5) . . . . ?
N1 C3 C4 C5 -1.3(10) . . . . ?
C3 C4 C5 C6 -1.1(10) . . . . ?
C3 C4 C5 C7 177.4(6) . . . . ?
N1 C2 C6 C5 -3.4(10) . . . . ?
C1 C2 C6 C5 171.7(6) . . . . ?
C4 C5 C6 C2 3.3(9) . . . . ?
C7 C5 C6 C2 -175.2(6) . . . . ?
C4 C5 C7 C8 175.8(6) . . . . ?
C6 C5 C7 C8 -5.7(10) . . . . ?
C4 C5 C7 C13 -7.5(9) . . . . ?
C6 C5 C7 C13 170.9(6) . . . . ?
C13 C7 C8 C9 1.9(10) . . . . ?
C5 C7 C8 C9 178.6(6) . . . . ?
C7 C8 C9 C10 -1.6(11) . . . . ?
C8 C9 C10 C11 0.9(11) . . . . ?
C9 C10 C11 C13 -0.5(10) . . . . ?
C9 C10 C11 C12 -176.6(6) . . . . ?
Zn1 O4 C12 O3 17.1(8) 2_546 . . . ?
Zn1 O4 C12 C11 -162.2(4) 2_546 . . . ?
C10 C11 C12 O3 1.0(10) . . . . ?
C13 C11 C12 O3 -175.2(6) . . . . ?
C10 C11 C12 O4 -179.8(6) . . . . ?
C13 C11 C12 O4 4.1(9) . . . . ?
C8 C7 C13 C11 -1.6(9) . . . . ?
C5 C7 C13 C11 -178.4(5) . . . . ?
C10 C11 C13 C7 0.9(9) . . . . ?
C12 C11 C13 C7 177.1(6) . . . . ?
C18 N2 C14 C15 -0.7(12) . . . . ?
Zn1 N2 C14 C15 176.3(6) . . . . ?
N2 C14 C15 C16 -0.9(13) . . . . ?
C14 C15 C16 C17 2.1(13) . . . . ?
C15 C16 C17 C18 -1.6(13) . . . . ?
C14 N2 C18 C17 1.1(10) . . . . ?
Zn1 N2 C18 C17 -176.1(5) . . . . ?
C14 N2 C18 C19 -177.0(7) . . . . ?
Zn1 N2 C18 C19 5.8(7) . . . . ?
C16 C17 C18 N2 0.0(11) . . . . ?
C16 C17 C18 C19 177.9(7) . . . . ?
C23 N3 C19 C20 -1.1(10) . . . . ?
Zn1 N3 C19 C20 -178.6(5) . . . . ?
C23 N3 C19 C18 177.7(6) . . . . ?
Zn1 N3 C19 C18 0.2(8) . . . . ?
N2 C18 C19 N3 -4.0(9) . . . . ?
C17 C18 C19 N3 177.9(6) . . . . ?
N2 C18 C19 C20 174.8(6) . . . . ?
C17 C18 C19 C20 -3.3(11) . . . . ?
N3 C19 C20 C21 1.2(11) . . . . ?
C18 C19 C20 C21 -177.4(7) . . . . ?
C19 C20 C21 C22 -0.2(13) . . . . ?
C20 C21 C22 C23 -0.9(14) . . . . ?
C19 N3 C23 C22 -0.1(11) . . . . ?
Zn1 N3 C23 C22 177.2(6) . . . . ?
C21 C22 C23 N3 1.1(13) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C22 H22 O2 0.93 2.50 3.111(9) 123.3 4_665
C17 H17 O1 0.93 2.41 3.214(8) 144.8 3_767
C3 H3 O3 0.93 2.58 3.279(8) 132.2 2_556

_refine_diff_density_max         0.452
_refine_diff_density_min         -0.416
_refine_diff_density_rms         0.091

####################################################################### 
# 
# 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_compound_8
_database_code_depnum_ccdc_archive 'CCDC 1505550'
_audit_update_record             
;
2016-11-11 deposited with the CCDC.
2016-11-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
#_shelx_SHELXL_version_number      '2014/7'
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H17 N3 O5 Zn'
_chemical_formula_weight         504.78

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

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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

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

_cell_length_a                   10.0211(5)
_cell_length_b                   11.6063(8)
_cell_length_c                   18.7216(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2177.5(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    8475
_cell_measurement_theta_min      3.457
_cell_measurement_theta_max      25.047

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.540
_exptl_crystal_F_000             1032
_exptl_transmission_factor_min   0.736
_exptl_transmission_factor_max   0.764
_exptl_crystal_size_max          0.270
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.230
_exptl_absorpt_coefficient_mu    1.172
_shelx_estimated_absorpt_T_min   0.743
_shelx_estimated_absorpt_T_max   0.774
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
#_exptl_absorpt_special_details    ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APE-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8475
_diffrn_reflns_av_unetI/netI     0.0855
_diffrn_reflns_av_R_equivalents  0.0560
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         3.457
_diffrn_reflns_theta_max         25.047
_diffrn_reflns_theta_full        25.047
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.960
_diffrn_reflns_point_group_measured_fraction_full 0.960
_reflns_number_total             3706
_reflns_number_gt                3034
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.684
_reflns_Friedel_fraction_max     0.911
_reflns_Friedel_fraction_full    0.911

_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0101P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 935 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.032(13)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3706
_refine_ls_number_parameters     307
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0641
_refine_ls_R_factor_gt           0.0464
_refine_ls_wR_factor_ref         0.0745
_refine_ls_wR_factor_gt          0.0646
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_restrained_S_all      1.074
_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 0.88779(6) 0.32765(7) 0.18039(4) 0.02664(19) Uani 1 1 d . . . . .
N1 N 1.4498(4) 0.6883(5) -0.2447(2) 0.0274(13) Uani 1 1 d . . . . .
N2 N 0.6997(4) 0.3378(5) 0.1268(3) 0.0303(13) Uani 1 1 d . . . . .
N3 N 0.7703(4) 0.1833(5) 0.2280(2) 0.0300(13) Uani 1 1 d . . . . .
O1 O 0.9604(4) 0.4611(4) 0.1157(2) 0.0346(12) Uani 1 1 d . . . . .
O2 O 1.1149(4) 0.3740(4) 0.0483(2) 0.0486(13) Uani 1 1 d . . . . .
O3 O 1.6068(4) 0.4792(4) -0.1367(2) 0.0361(11) Uani 1 1 d . . . . .
O4 O 1.6689(4) 0.5590(4) -0.2399(2) 0.0327(11) Uani 1 1 d . . . . .
O5 O 0.9670(4) 0.2109(4) 0.1069(2) 0.0366(12) Uani 1 1 d . . . . .
H1W H 1.0141 0.2536 0.0879 0.044 Uiso 1 1 d R U . . .
H2W H 1.0103 0.1499 0.1165 0.044 Uiso 1 1 d R U . . .
C1 C 1.0416(6) 0.4558(7) 0.0634(3) 0.0323(17) Uani 1 1 d . . . . .
C2 C 1.0453(6) 0.5616(6) 0.0165(3) 0.0305(16) Uani 1 1 d . . . . .
C3 C 0.9558(7) 0.6504(7) 0.0239(4) 0.062(2) Uani 1 1 d . . . . .
H3 H 0.8922 0.6471 0.0600 0.075 Uiso 1 1 calc R U . . .
C4 C 0.9583(8) 0.7438(8) -0.0209(5) 0.088(3) Uani 1 1 d . . . . .
H4 H 0.8972 0.8033 -0.0148 0.106 Uiso 1 1 calc R U . . .
C5 C 1.0525(7) 0.7497(7) -0.0755(4) 0.067(3) Uani 1 1 d . . . . .
H5 H 1.0537 0.8130 -0.1059 0.081 Uiso 1 1 calc R U . . .
C6 C 1.1443(5) 0.6619(6) -0.0847(3) 0.0319(16) Uani 1 1 d . . . . .
C7 C 1.1388(5) 0.5673(6) -0.0388(3) 0.0282(15) Uani 1 1 d . . . . .
H7 H 1.1985 0.5069 -0.0451 0.034 Uiso 1 1 calc R U . . .
C8 C 1.2494(5) 0.6701(6) -0.1410(3) 0.0274(14) Uani 1 1 d . . . . .
C9 C 1.2396(5) 0.7467(6) -0.1969(3) 0.0339(17) Uani 1 1 d . . . . .
H9 H 1.1654 0.7944 -0.2004 0.041 Uiso 1 1 calc R U . . .
C10 C 1.3397(5) 0.7535(6) -0.2480(3) 0.0334(17) Uani 1 1 d . . . . .
H10 H 1.3299 0.8049 -0.2858 0.040 Uiso 1 1 calc R U . . .
C11 C 1.4610(5) 0.6160(5) -0.1901(3) 0.0235(14) Uani 1 1 d . . . . .
C12 C 1.5891(5) 0.5447(5) -0.1883(3) 0.0278(14) Uani 1 1 d . . . . .
C13 C 1.3651(5) 0.6036(5) -0.1386(3) 0.0265(15) Uani 1 1 d . . . . .
H13 H 1.3773 0.5508 -0.1018 0.032 Uiso 1 1 calc R U . . .
C14 C 0.6660(6) 0.4158(7) 0.0786(3) 0.042(2) Uani 1 1 d . . . . .
H14 H 0.7269 0.4736 0.0675 0.050 Uiso 1 1 calc R U . . .
C15 C 0.5425(7) 0.4152(7) 0.0435(4) 0.048(2) Uani 1 1 d . . . . .
H15 H 0.5215 0.4720 0.0103 0.057 Uiso 1 1 calc R U . . .
C16 C 0.4536(6) 0.3293(7) 0.0588(3) 0.0453(19) Uani 1 1 d . . . . .
H16 H 0.3711 0.3275 0.0361 0.054 Uiso 1 1 calc R U . . .
C17 C 0.4865(6) 0.2442(7) 0.1087(3) 0.0348(18) Uani 1 1 d . . . . .
C18 C 0.6127(6) 0.2522(5) 0.1425(3) 0.0272(14) Uani 1 1 d . . . . .
C19 C 0.4019(6) 0.1496(7) 0.1270(3) 0.044(2) Uani 1 1 d . . . . .
H19 H 0.3206 0.1415 0.1035 0.053 Uiso 1 1 calc R U . . .
C20 C 0.4355(5) 0.0727(6) 0.1764(4) 0.0416(18) Uani 1 1 d . . . . .
H20 H 0.3778 0.0123 0.1870 0.050 Uiso 1 1 calc R U . . .
C21 C 0.5610(6) 0.0820(6) 0.2140(3) 0.0345(17) Uani 1 1 d . . . . .
C22 C 0.6494(5) 0.1711(6) 0.1953(3) 0.0270(14) Uani 1 1 d . . . . .
C23 C 0.5973(7) 0.0076(6) 0.2696(4) 0.0462(19) Uani 1 1 d . . . . .
H23 H 0.5401 -0.0512 0.2837 0.055 Uiso 1 1 calc R U . . .
C24 C 0.7188(6) 0.0222(7) 0.3033(4) 0.049(2) Uani 1 1 d . . . . .
H24 H 0.7446 -0.0257 0.3407 0.059 Uiso 1 1 calc R U . . .
C25 C 0.8009(6) 0.1102(6) 0.2798(3) 0.0379(18) Uani 1 1 d . . . . .
H25 H 0.8834 0.1187 0.3019 0.045 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Zn1 O4 2.069(4) 2_765 ?
Zn1 O5 2.088(4) . ?
Zn1 O1 2.097(4) . ?
Zn1 N2 2.138(4) . ?
Zn1 N1 2.157(4) 2_765 ?
Zn1 N3 2.234(5) . ?
N1 C11 1.327(7) . ?
N1 C10 1.340(6) . ?
N1 Zn1 2.157(4) 2_764 ?
N2 C14 1.323(8) . ?
N2 C18 1.354(7) . ?
N3 C25 1.323(7) . ?
N3 C22 1.365(6) . ?
O1 C1 1.275(7) . ?
O2 C1 1.234(8) . ?
O3 C12 1.242(7) . ?
O4 C12 1.265(6) . ?
O4 Zn1 2.069(4) 2_764 ?
O5 H1W 0.7703 . ?
O5 H2W 0.8500 . ?
C1 C2 1.510(9) . ?
C2 C3 1.373(8) . ?
C2 C7 1.398(7) . ?
C3 C4 1.371(10) . ?
C3 H3 0.9300 . ?
C4 C5 1.393(9) . ?
C4 H4 0.9300 . ?
C5 C6 1.383(9) . ?
C5 H5 0.9300 . ?
C6 C7 1.396(8) . ?
C6 C8 1.493(7) . ?
C7 H7 0.9300 . ?
C8 C9 1.376(8) . ?
C8 C13 1.393(7) . ?
C9 C10 1.389(7) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C11 C13 1.369(7) . ?
C11 C12 1.527(7) . ?
C13 H13 0.9300 . ?
C14 C15 1.401(8) . ?
C14 H14 0.9300 . ?
C15 C16 1.368(9) . ?
C15 H15 0.9300 . ?
C16 C17 1.398(9) . ?
C16 H16 0.9300 . ?
C17 C18 1.416(7) . ?
C17 C19 1.429(9) . ?
C18 C22 1.414(8) . ?
C19 C20 1.330(9) . ?
C19 H19 0.9300 . ?
C20 C21 1.444(8) . ?
C20 H20 0.9300 . ?
C21 C23 1.400(8) . ?
C21 C22 1.406(8) . ?
C23 C24 1.382(9) . ?
C23 H23 0.9300 . ?
C24 C25 1.384(9) . ?
C24 H24 0.9300 . ?
C25 H25 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O4 Zn1 O5 172.94(16) 2_765 . ?
O4 Zn1 O1 92.43(17) 2_765 . ?
O5 Zn1 O1 88.09(16) . . ?
O4 Zn1 N2 93.52(17) 2_765 . ?
O5 Zn1 N2 93.53(17) . . ?
O1 Zn1 N2 89.68(19) . . ?
O4 Zn1 N1 78.00(17) 2_765 2_765 ?
O5 Zn1 N1 94.97(17) . 2_765 ?
O1 Zn1 N1 100.21(17) . 2_765 ?
N2 Zn1 N1 167.15(18) . 2_765 ?
O4 Zn1 N3 92.52(18) 2_765 . ?
O5 Zn1 N3 88.67(17) . . ?
O1 Zn1 N3 165.43(16) . . ?
N2 Zn1 N3 76.35(19) . . ?
N1 Zn1 N3 94.22(18) 2_765 . ?
C11 N1 C10 117.6(5) . . ?
C11 N1 Zn1 112.5(4) . 2_764 ?
C10 N1 Zn1 129.7(4) . 2_764 ?
C14 N2 C18 119.1(5) . . ?
C14 N2 Zn1 125.7(4) . . ?
C18 N2 Zn1 115.2(4) . . ?
C25 N3 C22 117.9(6) . . ?
C25 N3 Zn1 130.6(4) . . ?
C22 N3 Zn1 111.5(4) . . ?
C1 O1 Zn1 129.0(5) . . ?
C12 O4 Zn1 117.5(4) . 2_764 ?
Zn1 O5 H1W 96.8 . . ?
Zn1 O5 H2W 126.5 . . ?
H1W O5 H2W 108.6 . . ?
O2 C1 O1 126.3(7) . . ?
O2 C1 C2 118.7(6) . . ?
O1 C1 C2 115.0(6) . . ?
C3 C2 C7 118.5(6) . . ?
C3 C2 C1 122.4(6) . . ?
C7 C2 C1 119.0(6) . . ?
C4 C3 C2 121.3(6) . . ?
C4 C3 H3 119.3 . . ?
C2 C3 H3 119.3 . . ?
C3 C4 C5 120.0(7) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C6 C5 C4 120.4(7) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
C5 C6 C7 118.4(5) . . ?
C5 C6 C8 120.7(6) . . ?
C7 C6 C8 120.8(6) . . ?
C6 C7 C2 121.3(6) . . ?
C6 C7 H7 119.3 . . ?
C2 C7 H7 119.3 . . ?
C9 C8 C13 116.2(5) . . ?
C9 C8 C6 121.8(5) . . ?
C13 C8 C6 122.0(6) . . ?
C8 C9 C10 120.6(6) . . ?
C8 C9 H9 119.7 . . ?
C10 C9 H9 119.7 . . ?
N1 C10 C9 122.0(6) . . ?
N1 C10 H10 119.0 . . ?
C9 C10 H10 119.0 . . ?
N1 C11 C13 123.3(5) . . ?
N1 C11 C12 115.5(5) . . ?
C13 C11 C12 121.2(5) . . ?
O3 C12 O4 125.8(5) . . ?
O3 C12 C11 118.0(5) . . ?
O4 C12 C11 116.3(5) . . ?
C11 C13 C8 120.2(5) . . ?
C11 C13 H13 119.9 . . ?
C8 C13 H13 119.9 . . ?
N2 C14 C15 122.8(7) . . ?
N2 C14 H14 118.6 . . ?
C15 C14 H14 118.6 . . ?
C16 C15 C14 118.7(7) . . ?
C16 C15 H15 120.6 . . ?
C14 C15 H15 120.6 . . ?
C15 C16 C17 120.1(6) . . ?
C15 C16 H16 120.0 . . ?
C17 C16 H16 120.0 . . ?
C16 C17 C18 117.5(6) . . ?
C16 C17 C19 124.2(6) . . ?
C18 C17 C19 118.2(7) . . ?
N2 C18 C22 118.2(5) . . ?
N2 C18 C17 121.8(6) . . ?
C22 C18 C17 120.0(6) . . ?
C20 C19 C17 122.1(6) . . ?
C20 C19 H19 118.9 . . ?
C17 C19 H19 118.9 . . ?
C19 C20 C21 120.6(6) . . ?
C19 C20 H20 119.7 . . ?
C21 C20 H20 119.7 . . ?
C23 C21 C22 118.3(6) . . ?
C23 C21 C20 122.8(6) . . ?
C22 C21 C20 118.8(6) . . ?
N3 C22 C21 121.6(6) . . ?
N3 C22 C18 118.4(6) . . ?
C21 C22 C18 120.0(5) . . ?
C24 C23 C21 119.6(6) . . ?
C24 C23 H23 120.2 . . ?
C21 C23 H23 120.2 . . ?
C23 C24 C25 117.9(7) . . ?
C23 C24 H24 121.0 . . ?
C25 C24 H24 121.0 . . ?
N3 C25 C24 124.7(6) . . ?
N3 C25 H25 117.7 . . ?
C24 C25 H25 117.7 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Zn1 O1 C1 O2 -15.3(9) . . . . ?
Zn1 O1 C1 C2 164.6(4) . . . . ?
O2 C1 C2 C3 171.7(7) . . . . ?
O1 C1 C2 C3 -8.2(9) . . . . ?
O2 C1 C2 C7 -5.1(9) . . . . ?
O1 C1 C2 C7 175.0(5) . . . . ?
C7 C2 C3 C4 -1.0(13) . . . . ?
C1 C2 C3 C4 -177.8(8) . . . . ?
C2 C3 C4 C5 0.4(15) . . . . ?
C3 C4 C5 C6 -0.3(15) . . . . ?
C4 C5 C6 C7 0.9(12) . . . . ?
C4 C5 C6 C8 -177.2(7) . . . . ?
C5 C6 C7 C2 -1.5(10) . . . . ?
C8 C6 C7 C2 176.6(5) . . . . ?
C3 C2 C7 C6 1.6(10) . . . . ?
C1 C2 C7 C6 178.5(5) . . . . ?
C5 C6 C8 C9 -17.4(10) . . . . ?
C7 C6 C8 C9 164.6(6) . . . . ?
C5 C6 C8 C13 160.2(7) . . . . ?
C7 C6 C8 C13 -17.8(9) . . . . ?
C13 C8 C9 C10 1.5(9) . . . . ?
C6 C8 C9 C10 179.2(6) . . . . ?
C11 N1 C10 C9 -0.1(9) . . . . ?
Zn1 N1 C10 C9 175.1(5) 2_764 . . . ?
C8 C9 C10 N1 -1.3(10) . . . . ?
C10 N1 C11 C13 1.3(8) . . . . ?
Zn1 N1 C11 C13 -174.8(5) 2_764 . . . ?
C10 N1 C11 C12 -179.3(5) . . . . ?
Zn1 N1 C11 C12 4.7(6) 2_764 . . . ?
Zn1 O4 C12 O3 179.1(5) 2_764 . . . ?
Zn1 O4 C12 C11 -1.6(7) 2_764 . . . ?
N1 C11 C12 O3 177.1(5) . . . . ?
C13 C11 C12 O3 -3.5(8) . . . . ?
N1 C11 C12 O4 -2.3(7) . . . . ?
C13 C11 C12 O4 177.2(5) . . . . ?
N1 C11 C13 C8 -1.0(9) . . . . ?
C12 C11 C13 C8 179.6(5) . . . . ?
C9 C8 C13 C11 -0.4(9) . . . . ?
C6 C8 C13 C11 -178.1(6) . . . . ?
C18 N2 C14 C15 1.1(10) . . . . ?
Zn1 N2 C14 C15 177.6(5) . . . . ?
N2 C14 C15 C16 -1.0(11) . . . . ?
C14 C15 C16 C17 -0.1(11) . . . . ?
C15 C16 C17 C18 0.9(10) . . . . ?
C15 C16 C17 C19 -178.3(6) . . . . ?
C14 N2 C18 C22 -178.6(5) . . . . ?
Zn1 N2 C18 C22 4.6(7) . . . . ?
C14 N2 C18 C17 -0.2(9) . . . . ?
Zn1 N2 C18 C17 -177.0(4) . . . . ?
C16 C17 C18 N2 -0.8(9) . . . . ?
C19 C17 C18 N2 178.5(5) . . . . ?
C16 C17 C18 C22 177.6(5) . . . . ?
C19 C17 C18 C22 -3.1(9) . . . . ?
C16 C17 C19 C20 -177.8(6) . . . . ?
C18 C17 C19 C20 3.0(10) . . . . ?
C17 C19 C20 C21 -0.1(10) . . . . ?
C19 C20 C21 C23 175.8(6) . . . . ?
C19 C20 C21 C22 -2.5(10) . . . . ?
C25 N3 C22 C21 -2.0(9) . . . . ?
Zn1 N3 C22 C21 176.8(4) . . . . ?
C25 N3 C22 C18 176.8(5) . . . . ?
Zn1 N3 C22 C18 -4.4(6) . . . . ?
C23 C21 C22 N3 2.6(9) . . . . ?
C20 C21 C22 N3 -178.9(5) . . . . ?
C23 C21 C22 C18 -176.1(5) . . . . ?
C20 C21 C22 C18 2.3(9) . . . . ?
N2 C18 C22 N3 0.1(8) . . . . ?
C17 C18 C22 N3 -178.3(5) . . . . ?
N2 C18 C22 C21 179.0(5) . . . . ?
C17 C18 C22 C21 0.5(8) . . . . ?
C22 C21 C23 C24 -1.3(9) . . . . ?
C20 C21 C23 C24 -179.6(6) . . . . ?
C21 C23 C24 C25 -0.7(10) . . . . ?
C22 N3 C25 C24 -0.1(10) . . . . ?
Zn1 N3 C25 C24 -178.6(5) . . . . ?
C23 C24 C25 N3 1.4(11) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O5 H1W O2 0.77 1.88 2.642(6) 171.9 .
O5 H2W O3 0.85 1.82 2.673(6) 178.7 3_455

_refine_diff_density_max         0.493
_refine_diff_density_min         -0.327
_refine_diff_density_rms         0.073

####################################################################### 
# 
# 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_compound_9
_database_code_depnum_ccdc_archive 'CCDC 1505551'
_audit_update_record             
;
2016-11-11 deposited with the CCDC.
2016-11-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
#_shelx_SHELXL_version_number      '2014/7'
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H17 Mn N3 O5'
_chemical_formula_weight         494.35

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Mn Mn 0.3368 0.7283 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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

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

_cell_length_a                   10.1184(4)
_cell_length_b                   11.5420(4)
_cell_length_c                   18.8913(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2206.23(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    8062
_cell_measurement_theta_min      3.438
_cell_measurement_theta_max      25.039

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.488
_exptl_crystal_F_000             1012
_exptl_transmission_factor_min   0.857
_exptl_transmission_factor_max   0.891
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    0.642
_shelx_estimated_absorpt_T_min   0.851
_shelx_estimated_absorpt_T_max   0.893
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
#_exptl_absorpt_special_details    ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APE-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8062
_diffrn_reflns_av_unetI/netI     0.0805
_diffrn_reflns_av_R_equivalents  0.0458
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         3.438
_diffrn_reflns_theta_max         25.039
_diffrn_reflns_theta_full        25.039
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3890
_reflns_number_gt                3044
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.750
_reflns_Friedel_fraction_max     0.999
_reflns_Friedel_fraction_full    0.999

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0202P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 963 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.003(18)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3890
_refine_ls_number_parameters     307
_refine_ls_number_restraints     7
_refine_ls_R_factor_all          0.0676
_refine_ls_R_factor_gt           0.0471
_refine_ls_wR_factor_ref         0.0820
_refine_ls_wR_factor_gt          0.0725
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_restrained_S_all      1.013
_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
Mn1 Mn 0.11368(8) 0.17260(6) 0.18102(4) 0.0315(2) Uani 1 1 d . . . . .
N1 N -0.0536(4) 0.1979(3) 0.2608(2) 0.0315(11) Uani 1 1 d . . . . .
N2 N 0.3120(4) 0.1678(4) 0.1275(2) 0.0356(11) Uani 1 1 d . . . . .
N3 N 0.2367(4) 0.3243(4) 0.2265(2) 0.0353(11) Uani 1 1 d . . . . .
O1 O 0.1599(4) 0.0619(3) 0.26739(19) 0.0423(10) Uani 1 1 d . . . . .
O2 O 0.0980(4) -0.0094(3) 0.3723(2) 0.0472(11) Uani 1 1 d . . . . .
O3 O -0.3867(5) -0.1172(3) 0.5495(2) 0.0555(12) Uani 1 1 d . . . . .
O4 O -0.5485(4) -0.0366(3) 0.6118(2) 0.0455(11) Uani 1 1 d . . . . .
O5 O 0.0221(4) 0.2894(3) 0.10724(19) 0.0487(12) Uani 1 1 d . . . . .
H2W H -0.0165 0.3540 0.1139 0.058 Uiso 1 1 d R U . . .
H1W H -0.0216 0.2442 0.0888 0.058 Uiso 1 1 d R U . . .
C1 C 0.0820(5) 0.0533(4) 0.3187(3) 0.0334(13) Uani 1 1 d . . . . .
C2 C -0.0439(5) 0.1242(4) 0.3154(3) 0.0290(12) Uani 1 1 d . . . . .
C3 C -0.1617(6) 0.2639(5) 0.2570(3) 0.0409(15) Uani 1 1 d . . . . .
H3 H -0.1691 0.3165 0.2199 0.049 Uiso 1 1 calc R U . . .
C4 C -0.2633(6) 0.2575(4) 0.3058(3) 0.0393(15) Uani 1 1 d . . . . .
H4 H -0.3360 0.3062 0.3013 0.047 Uiso 1 1 calc R U . . .
C5 C -0.2580(5) 0.1792(4) 0.3615(3) 0.0319(12) Uani 1 1 d . . . . .
C6 C -0.1427(6) 0.1127(4) 0.3655(3) 0.0332(14) Uani 1 1 d . . . . .
H6 H -0.1324 0.0601 0.4023 0.040 Uiso 1 1 calc R U . . .
C7 C -0.3653(6) 0.1687(4) 0.4144(3) 0.0364(13) Uani 1 1 d . . . . .
C8 C -0.4648(8) 0.2498(5) 0.4194(4) 0.076(3) Uani 1 1 d . . . . .
H8 H -0.4652 0.3128 0.3887 0.091 Uiso 1 1 calc R U . . .
C9 C -0.5630(9) 0.2390(7) 0.4688(4) 0.110(4) Uani 1 1 d . . . . .
H9 H -0.6305 0.2936 0.4703 0.131 Uiso 1 1 calc R U . . .
C10 C -0.5632(7) 0.1486(5) 0.5164(3) 0.073(2) Uani 1 1 d . . . . .
H10 H -0.6283 0.1440 0.5510 0.088 Uiso 1 1 calc R U . . .
C11 C -0.4662(6) 0.0650(4) 0.5123(3) 0.0362(14) Uani 1 1 d . . . . .
C12 C -0.4659(6) -0.0380(5) 0.5619(3) 0.0388(15) Uani 1 1 d . . . . .
C13 C -0.3691(6) 0.0757(4) 0.4614(3) 0.0339(13) Uani 1 1 d . . . . .
H13 H -0.3040 0.0190 0.4584 0.041 Uiso 1 1 calc R U . . .
C14 C 0.3512(6) 0.0893(5) 0.0801(3) 0.0485(18) Uani 1 1 d . . . . .
H14 H 0.2945 0.0284 0.0694 0.058 Uiso 1 1 calc R U . . .
C15 C 0.4724(7) 0.0942(6) 0.0463(3) 0.0564(19) Uani 1 1 d . . . . .
H15 H 0.4954 0.0375 0.0135 0.068 Uiso 1 1 calc R U . . .
C16 C 0.5573(6) 0.1814(6) 0.0608(3) 0.0559(18) Uani 1 1 d . . . . .
H16 H 0.6392 0.1842 0.0385 0.067 Uiso 1 1 calc R U . . .
C17 C 0.5216(6) 0.2678(5) 0.1096(3) 0.0423(15) Uani 1 1 d . . . . .
C18 C 0.3969(6) 0.2561(4) 0.1426(3) 0.0319(12) Uani 1 1 d . . . . .
C19 C 0.6028(6) 0.3641(5) 0.1281(3) 0.0524(17) Uani 1 1 d . . . . .
H19 H 0.6834 0.3740 0.1052 0.063 Uiso 1 1 calc R U . . .
C20 C 0.5659(6) 0.4409(6) 0.1776(4) 0.0574(18) Uani 1 1 d . . . . .
H20 H 0.6216 0.5025 0.1885 0.069 Uiso 1 1 calc R U . . .
C21 C 0.4423(6) 0.4300(5) 0.2139(3) 0.0444(16) Uani 1 1 d . . . . .
C22 C 0.3569(5) 0.3384(4) 0.1957(3) 0.0315(13) Uani 1 1 d . . . . .
C23 C 0.4026(7) 0.5038(5) 0.2687(3) 0.0554(15) Uani 1 1 d . U . . .
H23 H 0.4577 0.5640 0.2830 0.066 Uiso 1 1 calc R U . . .
C24 C 0.2832(7) 0.4880(5) 0.3015(3) 0.0552(15) Uani 1 1 d . U . . .
H24 H 0.2562 0.5360 0.3383 0.066 Uiso 1 1 calc R U . . .
C25 C 0.2030(7) 0.3972(5) 0.2776(3) 0.0477(17) Uani 1 1 d . . . . .
H25 H 0.1210 0.3874 0.2989 0.057 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Mn1 O1 2.125(3) . ?
Mn1 O4 2.148(4) 2_454 ?
Mn1 O5 2.149(3) . ?
Mn1 N2 2.248(4) . ?
Mn1 N1 2.285(4) . ?
Mn1 N3 2.313(4) . ?
N1 C3 1.335(6) . ?
N1 C2 1.340(6) . ?
N2 C14 1.333(6) . ?
N2 C18 1.363(6) . ?
N3 C25 1.325(6) . ?
N3 C22 1.359(6) . ?
O1 C1 1.252(6) . ?
O2 C1 1.256(6) . ?
O3 C12 1.238(7) . ?
O4 C12 1.260(6) . ?
O4 Mn1 2.148(4) 2_455 ?
O5 H2W 0.8503 . ?
O5 H1W 0.7674 . ?
C1 C2 1.516(7) . ?
C2 C6 1.383(7) . ?
C3 C4 1.383(7) . ?
C3 H3 0.9300 . ?
C4 C5 1.387(6) . ?
C4 H4 0.9300 . ?
C5 C6 1.399(7) . ?
C5 C7 1.481(6) . ?
C6 H6 0.9300 . ?
C7 C8 1.378(8) . ?
C7 C13 1.394(6) . ?
C8 C9 1.369(9) . ?
C8 H8 0.9300 . ?
C9 C10 1.377(8) . ?
C9 H9 0.9300 . ?
C10 C11 1.379(8) . ?
C10 H10 0.9300 . ?
C11 C13 1.379(7) . ?
C11 C12 1.514(7) . ?
C13 H13 0.9300 . ?
C14 C15 1.385(8) . ?
C14 H14 0.9300 . ?
C15 C16 1.351(9) . ?
C15 H15 0.9300 . ?
C16 C17 1.406(8) . ?
C16 H16 0.9300 . ?
C17 C18 1.413(7) . ?
C17 C19 1.426(7) . ?
C18 C22 1.440(7) . ?
C19 C20 1.342(8) . ?
C19 H19 0.9300 . ?
C20 C21 1.432(8) . ?
C20 H20 0.9300 . ?
C21 C23 1.400(8) . ?
C21 C22 1.407(7) . ?
C23 C24 1.370(9) . ?
C23 H23 0.9300 . ?
C24 C25 1.401(7) . ?
C24 H24 0.9300 . ?
C25 H25 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Mn1 O4 95.48(14) . 2_454 ?
O1 Mn1 O5 165.97(16) . . ?
O4 Mn1 O5 86.05(13) 2_454 . ?
O1 Mn1 N2 97.74(15) . . ?
O4 Mn1 N2 88.97(16) 2_454 . ?
O5 Mn1 N2 96.23(16) . . ?
O1 Mn1 N1 74.53(14) . . ?
O4 Mn1 N1 105.54(15) 2_454 . ?
O5 Mn1 N1 91.61(15) . . ?
N2 Mn1 N1 163.98(16) . . ?
O1 Mn1 N3 92.98(15) . . ?
O4 Mn1 N3 160.86(16) 2_454 . ?
O5 Mn1 N3 89.88(14) . . ?
N2 Mn1 N3 72.87(16) . . ?
N1 Mn1 N3 93.25(15) . . ?
C3 N1 C2 117.6(5) . . ?
C3 N1 Mn1 130.1(3) . . ?
C2 N1 Mn1 111.8(3) . . ?
C14 N2 C18 117.4(5) . . ?
C14 N2 Mn1 125.7(4) . . ?
C18 N2 Mn1 116.8(3) . . ?
C25 N3 C22 117.8(5) . . ?
C25 N3 Mn1 127.8(4) . . ?
C22 N3 Mn1 114.4(3) . . ?
C1 O1 Mn1 120.2(3) . . ?
C12 O4 Mn1 130.5(4) . 2_455 ?
Mn1 O5 H2W 130.6 . . ?
Mn1 O5 H1W 96.6 . . ?
H2W O5 H1W 113.5 . . ?
O1 C1 O2 126.1(5) . . ?
O1 C1 C2 117.0(5) . . ?
O2 C1 C2 116.9(5) . . ?
N1 C2 C6 122.3(5) . . ?
N1 C2 C1 115.9(5) . . ?
C6 C2 C1 121.9(5) . . ?
N1 C3 C4 122.9(5) . . ?
N1 C3 H3 118.6 . . ?
C4 C3 H3 118.6 . . ?
C3 C4 C5 120.8(5) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 H4 119.6 . . ?
C4 C5 C6 115.5(5) . . ?
C4 C5 C7 122.5(5) . . ?
C6 C5 C7 122.0(5) . . ?
C2 C6 C5 120.9(5) . . ?
C2 C6 H6 119.6 . . ?
C5 C6 H6 119.6 . . ?
C8 C7 C13 117.3(5) . . ?
C8 C7 C5 121.7(5) . . ?
C13 C7 C5 120.9(5) . . ?
C9 C8 C7 121.1(6) . . ?
C9 C8 H8 119.5 . . ?
C7 C8 H8 119.5 . . ?
C8 C9 C10 121.0(7) . . ?
C8 C9 H9 119.5 . . ?
C10 C9 H9 119.5 . . ?
C9 C10 C11 119.5(6) . . ?
C9 C10 H10 120.3 . . ?
C11 C10 H10 120.3 . . ?
C13 C11 C10 118.9(5) . . ?
C13 C11 C12 120.0(5) . . ?
C10 C11 C12 121.1(5) . . ?
O3 C12 O4 125.4(5) . . ?
O3 C12 C11 117.7(5) . . ?
O4 C12 C11 116.8(5) . . ?
C11 C13 C7 122.2(5) . . ?
C11 C13 H13 118.9 . . ?
C7 C13 H13 118.9 . . ?
N2 C14 C15 123.1(6) . . ?
N2 C14 H14 118.4 . . ?
C15 C14 H14 118.4 . . ?
C16 C15 C14 120.0(6) . . ?
C16 C15 H15 120.0 . . ?
C14 C15 H15 120.0 . . ?
C15 C16 C17 119.9(6) . . ?
C15 C16 H16 120.1 . . ?
C17 C16 H16 120.1 . . ?
C16 C17 C18 116.8(5) . . ?
C16 C17 C19 124.4(6) . . ?
C18 C17 C19 118.8(6) . . ?
N2 C18 C17 122.8(5) . . ?
N2 C18 C22 117.5(5) . . ?
C17 C18 C22 119.7(5) . . ?
C20 C19 C17 121.7(6) . . ?
C20 C19 H19 119.2 . . ?
C17 C19 H19 119.2 . . ?
C19 C20 C21 121.3(6) . . ?
C19 C20 H20 119.4 . . ?
C21 C20 H20 119.4 . . ?
C23 C21 C22 117.5(6) . . ?
C23 C21 C20 123.4(6) . . ?
C22 C21 C20 119.0(6) . . ?
N3 C22 C21 122.3(5) . . ?
N3 C22 C18 118.1(5) . . ?
C21 C22 C18 119.6(5) . . ?
C24 C23 C21 120.4(6) . . ?
C24 C23 H23 119.8 . . ?
C21 C23 H23 119.8 . . ?
C23 C24 C25 117.7(6) . . ?
C23 C24 H24 121.2 . . ?
C25 C24 H24 121.2 . . ?
N3 C25 C24 124.2(6) . . ?
N3 C25 H25 117.9 . . ?
C24 C25 H25 117.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Mn1 O1 C1 O2 179.6(4) . . . . ?
Mn1 O1 C1 C2 0.3(6) . . . . ?
C3 N1 C2 C6 2.0(7) . . . . ?
Mn1 N1 C2 C6 -171.4(4) . . . . ?
C3 N1 C2 C1 -178.5(4) . . . . ?
Mn1 N1 C2 C1 8.2(5) . . . . ?
O1 C1 C2 N1 -6.2(7) . . . . ?
O2 C1 C2 N1 174.5(4) . . . . ?
O1 C1 C2 C6 173.4(5) . . . . ?
O2 C1 C2 C6 -6.0(7) . . . . ?
C2 N1 C3 C4 -1.2(8) . . . . ?
Mn1 N1 C3 C4 170.7(4) . . . . ?
N1 C3 C4 C5 -1.0(9) . . . . ?
C3 C4 C5 C6 2.3(8) . . . . ?
C3 C4 C5 C7 -179.3(5) . . . . ?
N1 C2 C6 C5 -0.6(8) . . . . ?
C1 C2 C6 C5 179.9(4) . . . . ?
C4 C5 C6 C2 -1.6(7) . . . . ?
C7 C5 C6 C2 -179.9(5) . . . . ?
C4 C5 C7 C8 -12.2(9) . . . . ?
C6 C5 C7 C8 166.0(6) . . . . ?
C4 C5 C7 C13 167.8(5) . . . . ?
C6 C5 C7 C13 -13.9(8) . . . . ?
C13 C7 C8 C9 0.2(12) . . . . ?
C5 C7 C8 C9 -179.8(8) . . . . ?
C7 C8 C9 C10 1.9(15) . . . . ?
C8 C9 C10 C11 -2.8(14) . . . . ?
C9 C10 C11 C13 1.6(11) . . . . ?
C9 C10 C11 C12 -177.8(7) . . . . ?
Mn1 O4 C12 O3 -12.9(9) 2_455 . . . ?
Mn1 O4 C12 C11 165.7(4) 2_455 . . . ?
C13 C11 C12 O3 -8.6(8) . . . . ?
C10 C11 C12 O3 170.8(6) . . . . ?
C13 C11 C12 O4 172.7(5) . . . . ?
C10 C11 C12 O4 -8.0(9) . . . . ?
C10 C11 C13 C7 0.5(9) . . . . ?
C12 C11 C13 C7 179.8(5) . . . . ?
C8 C7 C13 C11 -1.4(9) . . . . ?
C5 C7 C13 C11 178.6(5) . . . . ?
C18 N2 C14 C15 -0.2(8) . . . . ?
Mn1 N2 C14 C15 176.7(5) . . . . ?
N2 C14 C15 C16 0.2(10) . . . . ?
C14 C15 C16 C17 -0.8(9) . . . . ?
C15 C16 C17 C18 1.5(8) . . . . ?
C15 C16 C17 C19 -179.1(6) . . . . ?
C14 N2 C18 C17 1.0(7) . . . . ?
Mn1 N2 C18 C17 -176.2(4) . . . . ?
C14 N2 C18 C22 -177.6(4) . . . . ?
Mn1 N2 C18 C22 5.2(6) . . . . ?
C16 C17 C18 N2 -1.6(8) . . . . ?
C19 C17 C18 N2 179.0(5) . . . . ?
C16 C17 C18 C22 177.0(5) . . . . ?
C19 C17 C18 C22 -2.5(7) . . . . ?
C16 C17 C19 C20 -176.8(6) . . . . ?
C18 C17 C19 C20 2.6(8) . . . . ?
C17 C19 C20 C21 -0.5(9) . . . . ?
C19 C20 C21 C23 176.2(6) . . . . ?
C19 C20 C21 C22 -1.7(9) . . . . ?
C25 N3 C22 C21 -3.1(7) . . . . ?
Mn1 N3 C22 C21 176.6(4) . . . . ?
C25 N3 C22 C18 177.0(4) . . . . ?
Mn1 N3 C22 C18 -3.4(5) . . . . ?
C23 C21 C22 N3 3.7(8) . . . . ?
C20 C21 C22 N3 -178.2(5) . . . . ?
C23 C21 C22 C18 -176.3(5) . . . . ?
C20 C21 C22 C18 1.8(7) . . . . ?
N2 C18 C22 N3 -1.1(7) . . . . ?
C17 C18 C22 N3 -179.7(5) . . . . ?
N2 C18 C22 C21 179.0(4) . . . . ?
C17 C18 C22 C21 0.3(7) . . . . ?
C22 C21 C23 C24 -1.7(9) . . . . ?
C20 C21 C23 C24 -179.7(6) . . . . ?
C21 C23 C24 C25 -0.8(9) . . . . ?
C22 N3 C25 C24 0.4(8) . . . . ?
Mn1 N3 C25 C24 -179.2(4) . . . . ?
C23 C24 C25 N3 1.5(9) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O5 H2W O2 0.85 1.80 2.649(5) 179.8 4
O5 H1W O3 0.77 1.89 2.649(5) 171.9 2_454

_refine_diff_density_max         0.306
_refine_diff_density_min         -0.270
_refine_diff_density_rms         0.054

####################################################################### 
# 
# 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_compound_10
_database_code_depnum_ccdc_archive 'CCDC 1505552'
_audit_update_record             
;
2016-11-11 deposited with the CCDC.
2016-11-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
#_shelx_SHELXL_version_number      '2014/7'
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H17 Cu N3 O5'
_chemical_formula_weight         502.95

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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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

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

_cell_length_a                   10.0257(3)
_cell_length_b                   11.6347(6)
_cell_length_c                   18.6389(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2174.16(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    8242
_cell_measurement_theta_min      3.460
_cell_measurement_theta_max      25.047

_exptl_crystal_description       block
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.537
_exptl_crystal_F_000             1028
_exptl_transmission_factor_min   0.769
_exptl_transmission_factor_max   0.811
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.260
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    1.049
_shelx_estimated_absorpt_T_min   0.772
_shelx_estimated_absorpt_T_max   0.818
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
#_exptl_absorpt_special_details    ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APE-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8242
_diffrn_reflns_av_unetI/netI     0.0702
_diffrn_reflns_av_R_equivalents  0.0410
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         3.460
_diffrn_reflns_theta_max         25.047
_diffrn_reflns_theta_full        25.047
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3841
_reflns_number_gt                3317
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.751
_reflns_Friedel_fraction_max     0.999
_reflns_Friedel_fraction_full    0.999

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0614P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1166 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.080(12)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3841
_refine_ls_number_parameters     307
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0637
_refine_ls_R_factor_gt           0.0522
_refine_ls_wR_factor_ref         0.1327
_refine_ls_wR_factor_gt          0.1218
_refine_ls_goodness_of_fit_ref   1.137
_refine_ls_restrained_S_all      1.137
_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 0.88528(8) 0.17443(9) 0.18161(4) 0.0280(3) Uani 1 1 d . . . . .
N1 N 1.0503(5) 0.1863(5) 0.2548(2) 0.0208(13) Uani 1 1 d . . . . .
N2 N 0.7710(5) 0.3145(6) 0.2282(3) 0.0262(14) Uani 1 1 d . . . . .
N3 N 0.7011(5) 0.1614(6) 0.1260(2) 0.0244(13) Uani 1 1 d . . . . .
O1 O 0.8285(4) 0.0637(5) 0.2614(2) 0.0279(12) Uani 1 1 d . . . . .
O2 O 0.8927(5) -0.0234(5) 0.3626(2) 0.0334(12) Uani 1 1 d . . . . .
O3 O 1.3864(6) -0.1285(5) 0.5491(3) 0.0408(13) Uani 1 1 d . . . . .
O4 O 1.5383(5) -0.0407(5) 0.6178(2) 0.0302(12) Uani 1 1 d . . . . .
O5 O 0.9639(5) 0.2905(4) 0.1075(2) 0.0284(12) Uani 1 1 d . . . . .
H1W H 1.0096 0.3501 0.1170 0.034 Uiso 1 1 d R U . . .
H2W H 1.0115 0.2382 0.0785 0.034 Uiso 1 1 d R U . . .
C1 C 0.9090(6) 0.0453(6) 0.3120(3) 0.0233(15) Uani 1 1 d . . . . .
C2 C 1.0389(6) 0.1128(6) 0.3093(3) 0.0200(14) Uani 1 1 d . . . . .
C3 C 1.1607(6) 0.2504(8) 0.2514(3) 0.0300(18) Uani 1 1 d . . . . .
H3 H 1.1709 0.3014 0.2134 0.036 Uiso 1 1 calc R U . . .
C4 C 1.2607(7) 0.2434(8) 0.3027(3) 0.0336(19) Uani 1 1 d . . . . .
H4 H 1.3353 0.2905 0.2990 0.040 Uiso 1 1 calc R U . . .
C5 C 1.2507(6) 0.1679(7) 0.3586(3) 0.0236(15) Uani 1 1 d . . . . .
C6 C 1.1349(7) 0.1018(6) 0.3617(3) 0.0254(16) Uani 1 1 d . . . . .
H6 H 1.1225 0.0502 0.3992 0.030 Uiso 1 1 calc R U . . .
C7 C 1.3543(6) 0.1613(7) 0.4164(3) 0.0281(16) Uani 1 1 d . . . . .
C8 C 1.4448(9) 0.2458(8) 0.4261(5) 0.054(3) Uani 1 1 d . . . . .
H8 H 1.4451 0.3083 0.3949 0.065 Uiso 1 1 calc R U . . .
C9 C 1.5385(11) 0.2419(10) 0.4820(5) 0.069(3) Uani 1 1 d . . . . .
H9 H 1.5983 0.3021 0.4884 0.083 Uiso 1 1 calc R U . . .
C10 C 1.5413(10) 0.1514(8) 0.5258(5) 0.059(3) Uani 1 1 d . . . . .
H10 H 1.6039 0.1490 0.5626 0.071 Uiso 1 1 calc R U . . .
C11 C 1.4520(7) 0.0601(7) 0.5174(3) 0.0261(16) Uani 1 1 d . . . . .
C12 C 1.4572(7) -0.0469(7) 0.5651(3) 0.0255(16) Uani 1 1 d . . . . .
C13 C 1.3603(6) 0.0646(7) 0.4618(3) 0.0238(15) Uani 1 1 d . . . . .
H13 H 1.3024 0.0033 0.4544 0.029 Uiso 1 1 calc R U . . .
C14 C 0.8024(8) 0.3871(7) 0.2806(4) 0.0329(19) Uani 1 1 d . . . . .
H14 H 0.8845 0.3786 0.3032 0.040 Uiso 1 1 calc R U . . .
C15 C 0.7185(8) 0.4751(8) 0.3033(4) 0.041(2) Uani 1 1 d . . . . .
H15 H 0.7442 0.5234 0.3406 0.049 Uiso 1 1 calc R U . . .
C16 C 0.5981(9) 0.4900(7) 0.2704(4) 0.042(2) Uani 1 1 d . . . . .
H16 H 0.5416 0.5490 0.2849 0.050 Uiso 1 1 calc R U . . .
C17 C 0.5596(7) 0.4149(7) 0.2142(4) 0.0323(19) Uani 1 1 d . . . . .
C18 C 0.6492(6) 0.3279(7) 0.1950(3) 0.0237(15) Uani 1 1 d . . . . .
C19 C 0.4347(7) 0.4253(8) 0.1762(4) 0.038(2) Uani 1 1 d . . . . .
H19 H 0.3777 0.4864 0.1859 0.046 Uiso 1 1 calc R U . . .
C20 C 0.4010(7) 0.3464(8) 0.1268(4) 0.040(2) Uani 1 1 d . . . . .
H20 H 0.3188 0.3523 0.1040 0.049 Uiso 1 1 calc R U . . .
C21 C 0.4868(6) 0.2551(8) 0.1085(3) 0.0284(18) Uani 1 1 d . . . . .
C22 C 0.6138(7) 0.2461(7) 0.1412(3) 0.0238(15) Uani 1 1 d . . . . .
C23 C 0.4541(7) 0.1671(8) 0.0575(3) 0.037(2) Uani 1 1 d . . . . .
H23 H 0.3719 0.1678 0.0344 0.045 Uiso 1 1 calc R U . . .
C24 C 0.5435(8) 0.0830(8) 0.0434(4) 0.042(2) Uani 1 1 d . . . . .
H24 H 0.5225 0.0256 0.0105 0.050 Uiso 1 1 calc R U . . .
C25 C 0.6664(8) 0.0820(8) 0.0777(4) 0.037(2) Uani 1 1 d . . . . .
H25 H 0.7268 0.0240 0.0666 0.044 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 O1 2.049(5) . ?
Cu1 O5 2.086(5) . ?
Cu1 O4 2.104(5) 2_754 ?
Cu1 N3 2.123(5) . ?
Cu1 N1 2.149(5) . ?
Cu1 N2 2.174(6) . ?
N1 C2 1.332(8) . ?
N1 C3 1.336(8) . ?
N2 C14 1.329(9) . ?
N2 C18 1.377(8) . ?
N3 C25 1.335(9) . ?
N3 C22 1.349(9) . ?
O1 C1 1.260(7) . ?
O2 C1 1.247(8) . ?
O3 C12 1.223(9) . ?
O4 C12 1.276(8) . ?
O4 Cu1 2.104(5) 2_755 ?
O5 H1W 0.8499 . ?
O5 H2W 0.9428 . ?
C1 C2 1.522(9) . ?
C2 C6 1.377(9) . ?
C3 C4 1.388(9) . ?
C3 H3 0.9300 . ?
C4 C5 1.366(10) . ?
C4 H4 0.9300 . ?
C5 C6 1.394(10) . ?
C5 C7 1.500(8) . ?
C6 H6 0.9300 . ?
C7 C8 1.350(11) . ?
C7 C13 1.409(10) . ?
C8 C9 1.403(11) . ?
C8 H8 0.9300 . ?
C9 C10 1.332(13) . ?
C9 H9 0.9300 . ?
C10 C11 1.398(11) . ?
C10 H10 0.9300 . ?
C11 C13 1.386(8) . ?
C11 C12 1.532(10) . ?
C13 H13 0.9300 . ?
C14 C15 1.391(11) . ?
C14 H14 0.9300 . ?
C15 C16 1.365(12) . ?
C15 H15 0.9300 . ?
C16 C17 1.417(11) . ?
C16 H16 0.9300 . ?
C17 C18 1.400(10) . ?
C17 C19 1.444(10) . ?
C18 C22 1.428(10) . ?
C19 C20 1.344(11) . ?
C19 H19 0.9300 . ?
C20 C21 1.408(11) . ?
C20 H20 0.9300 . ?
C21 C22 1.416(9) . ?
C21 C23 1.435(11) . ?
C23 C24 1.353(12) . ?
C23 H23 0.9300 . ?
C24 C25 1.389(11) . ?
C24 H24 0.9300 . ?
C25 H25 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Cu1 O5 173.13(19) . . ?
O1 Cu1 O4 92.7(2) . 2_754 ?
O5 Cu1 O4 88.09(18) . 2_754 ?
O1 Cu1 N3 93.9(2) . . ?
O5 Cu1 N3 92.9(2) . . ?
O4 Cu1 N3 89.3(2) 2_754 . ?
O1 Cu1 N1 78.08(18) . . ?
O5 Cu1 N1 95.06(19) . . ?
O4 Cu1 N1 97.2(2) 2_754 . ?
N3 Cu1 N1 169.83(18) . . ?
O1 Cu1 N2 92.0(2) . . ?
O5 Cu1 N2 88.7(2) . . ?
O4 Cu1 N2 166.62(19) 2_754 . ?
N3 Cu1 N2 77.9(2) . . ?
N1 Cu1 N2 96.0(2) . . ?
C2 N1 C3 117.8(5) . . ?
C2 N1 Cu1 112.1(4) . . ?
C3 N1 Cu1 130.0(4) . . ?
C14 N2 C18 117.9(6) . . ?
C14 N2 Cu1 130.2(5) . . ?
C18 N2 Cu1 111.9(5) . . ?
C25 N3 C22 118.6(6) . . ?
C25 N3 Cu1 127.3(5) . . ?
C22 N3 Cu1 114.2(4) . . ?
C1 O1 Cu1 118.2(4) . . ?
C12 O4 Cu1 128.7(5) . 2_755 ?
Cu1 O5 H1W 126.5 . . ?
Cu1 O5 H2W 98.8 . . ?
H1W O5 H2W 111.9 . . ?
O2 C1 O1 126.2(6) . . ?
O2 C1 C2 117.9(6) . . ?
O1 C1 C2 115.9(6) . . ?
N1 C2 C6 122.7(6) . . ?
N1 C2 C1 115.5(5) . . ?
C6 C2 C1 121.8(6) . . ?
N1 C3 C4 122.2(6) . . ?
N1 C3 H3 118.9 . . ?
C4 C3 H3 118.9 . . ?
C5 C4 C3 120.7(7) . . ?
C5 C4 H4 119.7 . . ?
C3 C4 H4 119.7 . . ?
C4 C5 C6 116.6(6) . . ?
C4 C5 C7 122.1(6) . . ?
C6 C5 C7 121.2(6) . . ?
C2 C6 C5 120.1(6) . . ?
C2 C6 H6 120.0 . . ?
C5 C6 H6 120.0 . . ?
C8 C7 C13 118.2(6) . . ?
C8 C7 C5 121.6(7) . . ?
C13 C7 C5 120.1(7) . . ?
C7 C8 C9 121.7(8) . . ?
C7 C8 H8 119.2 . . ?
C9 C8 H8 119.2 . . ?
C10 C9 C8 119.7(9) . . ?
C10 C9 H9 120.2 . . ?
C8 C9 H9 120.2 . . ?
C9 C10 C11 121.2(7) . . ?
C9 C10 H10 119.4 . . ?
C11 C10 H10 119.4 . . ?
C13 C11 C10 118.7(7) . . ?
C13 C11 C12 119.1(7) . . ?
C10 C11 C12 122.1(6) . . ?
O3 C12 O4 127.1(7) . . ?
O3 C12 C11 118.0(6) . . ?
O4 C12 C11 115.0(7) . . ?
C11 C13 C7 120.4(7) . . ?
C11 C13 H13 119.8 . . ?
C7 C13 H13 119.8 . . ?
N2 C14 C15 123.2(7) . . ?
N2 C14 H14 118.4 . . ?
C15 C14 H14 118.4 . . ?
C16 C15 C14 119.4(7) . . ?
C16 C15 H15 120.3 . . ?
C14 C15 H15 120.3 . . ?
C15 C16 C17 119.6(8) . . ?
C15 C16 H16 120.2 . . ?
C17 C16 H16 120.2 . . ?
C18 C17 C16 117.4(7) . . ?
C18 C17 C19 119.4(7) . . ?
C16 C17 C19 123.2(8) . . ?
N2 C18 C17 122.4(7) . . ?
N2 C18 C22 117.4(6) . . ?
C17 C18 C22 120.2(6) . . ?
C20 C19 C17 119.9(8) . . ?
C20 C19 H19 120.1 . . ?
C17 C19 H19 120.1 . . ?
C19 C20 C21 121.8(7) . . ?
C19 C20 H20 119.1 . . ?
C21 C20 H20 119.1 . . ?
C20 C21 C22 120.1(7) . . ?
C20 C21 C23 124.0(6) . . ?
C22 C21 C23 115.9(7) . . ?
N3 C22 C21 123.2(7) . . ?
N3 C22 C18 118.3(6) . . ?
C21 C22 C18 118.5(7) . . ?
C24 C23 C21 119.6(6) . . ?
C24 C23 H23 120.2 . . ?
C21 C23 H23 120.2 . . ?
C23 C24 C25 120.3(8) . . ?
C23 C24 H24 119.9 . . ?
C25 C24 H24 119.9 . . ?
N3 C25 C24 122.4(8) . . ?
N3 C25 H25 118.8 . . ?
C24 C25 H25 118.8 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cu1 O1 C1 O2 -176.4(5) . . . . ?
Cu1 O1 C1 C2 2.6(7) . . . . ?
C3 N1 C2 C6 0.7(10) . . . . ?
Cu1 N1 C2 C6 177.6(5) . . . . ?
C3 N1 C2 C1 177.9(6) . . . . ?
Cu1 N1 C2 C1 -5.1(7) . . . . ?
O2 C1 C2 N1 -178.9(6) . . . . ?
O1 C1 C2 N1 2.0(9) . . . . ?
O2 C1 C2 C6 -1.7(10) . . . . ?
O1 C1 C2 C6 179.2(6) . . . . ?
C2 N1 C3 C4 -0.8(11) . . . . ?
Cu1 N1 C3 C4 -177.2(6) . . . . ?
N1 C3 C4 C5 1.3(12) . . . . ?
C3 C4 C5 C6 -1.4(11) . . . . ?
C3 C4 C5 C7 -177.6(7) . . . . ?
N1 C2 C6 C5 -0.9(10) . . . . ?
C1 C2 C6 C5 -177.9(6) . . . . ?
C4 C5 C6 C2 1.2(10) . . . . ?
C7 C5 C6 C2 177.4(7) . . . . ?
C4 C5 C7 C8 16.0(11) . . . . ?
C6 C5 C7 C8 -160.0(8) . . . . ?
C4 C5 C7 C13 -163.1(7) . . . . ?
C6 C5 C7 C13 20.9(10) . . . . ?
C13 C7 C8 C9 -3.4(14) . . . . ?
C5 C7 C8 C9 177.5(9) . . . . ?
C7 C8 C9 C10 1.8(18) . . . . ?
C8 C9 C10 C11 -0.3(18) . . . . ?
C9 C10 C11 C13 0.7(15) . . . . ?
C9 C10 C11 C12 177.4(10) . . . . ?
Cu1 O4 C12 O3 15.5(11) 2_755 . . . ?
Cu1 O4 C12 C11 -163.6(4) 2_755 . . . ?
C13 C11 C12 O3 5.3(10) . . . . ?
C10 C11 C12 O3 -171.5(8) . . . . ?
C13 C11 C12 O4 -175.6(6) . . . . ?
C10 C11 C12 O4 7.7(11) . . . . ?
C10 C11 C13 C7 -2.4(11) . . . . ?
C12 C11 C13 C7 -179.2(6) . . . . ?
C8 C7 C13 C11 3.7(11) . . . . ?
C5 C7 C13 C11 -177.1(6) . . . . ?
C18 N2 C14 C15 0.0(11) . . . . ?
Cu1 N2 C14 C15 178.3(6) . . . . ?
N2 C14 C15 C16 -0.7(12) . . . . ?
C14 C15 C16 C17 0.7(12) . . . . ?
C15 C16 C17 C18 0.0(11) . . . . ?
C15 C16 C17 C19 -179.4(7) . . . . ?
C14 N2 C18 C17 0.6(10) . . . . ?
Cu1 N2 C18 C17 -177.9(5) . . . . ?
C14 N2 C18 C22 -177.1(6) . . . . ?
Cu1 N2 C18 C22 4.3(7) . . . . ?
C16 C17 C18 N2 -0.6(10) . . . . ?
C19 C17 C18 N2 178.8(6) . . . . ?
C16 C17 C18 C22 177.0(6) . . . . ?
C19 C17 C18 C22 -3.6(10) . . . . ?
C18 C17 C19 C20 5.1(11) . . . . ?
C16 C17 C19 C20 -175.6(7) . . . . ?
C17 C19 C20 C21 -2.5(12) . . . . ?
C19 C20 C21 C22 -1.6(11) . . . . ?
C19 C20 C21 C23 178.3(7) . . . . ?
C25 N3 C22 C21 0.1(10) . . . . ?
Cu1 N3 C22 C21 178.3(5) . . . . ?
C25 N3 C22 C18 177.4(6) . . . . ?
Cu1 N3 C22 C18 -4.4(7) . . . . ?
C20 C21 C22 N3 -179.6(6) . . . . ?
C23 C21 C22 N3 0.4(10) . . . . ?
C20 C21 C22 C18 3.1(10) . . . . ?
C23 C21 C22 C18 -176.8(6) . . . . ?
N2 C18 C22 N3 -0.1(9) . . . . ?
C17 C18 C22 N3 -177.9(6) . . . . ?
N2 C18 C22 C21 177.3(6) . . . . ?
C17 C18 C22 C21 -0.4(9) . . . . ?
C20 C21 C23 C24 179.7(7) . . . . ?
C22 C21 C23 C24 -0.3(11) . . . . ?
C21 C23 C24 C25 -0.2(12) . . . . ?
C22 N3 C25 C24 -0.7(11) . . . . ?
Cu1 N3 C25 C24 -178.7(6) . . . . ?
C23 C24 C25 N3 0.8(13) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O5 H1W O2 0.85 1.81 2.659(7) 179.7 4_755
O5 H2W O3 0.94 1.73 2.645(7) 163.6 2_754

_refine_diff_density_max         0.441
_refine_diff_density_min         -0.426
_refine_diff_density_rms         0.079

####################################################################### 
# 
# 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_compound_11
_database_code_depnum_ccdc_archive 'CCDC 1505553'
_audit_update_record             
;
2016-11-21 deposited with the CCDC.
2016-11-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
#_shelx_SHELXL_version_number      '2014/7'
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C63 H45 Cd3 N7 O16'
_chemical_formula_weight         1493.26

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'
Cd Cd -0.8075 1.2024 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   10.9405(7)
_cell_length_b                   21.7240(17)
_cell_length_c                   23.8970(11)
_cell_angle_alpha                90
_cell_angle_beta                 91.988(5)
_cell_angle_gamma                90
_cell_volume                     5676.2(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    23475
_cell_measurement_theta_min      3.348
_cell_measurement_theta_max      25.050

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.738
_exptl_crystal_F_000             2944
_exptl_transmission_factor_min   0.748
_exptl_transmission_factor_max   0.788
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    1.194
_shelx_estimated_absorpt_T_min   0.731
_shelx_estimated_absorpt_T_max   0.796
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
#_exptl_absorpt_special_details    ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APE-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            23475
_diffrn_reflns_av_unetI/netI     0.1032
_diffrn_reflns_av_R_equivalents  0.0627
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         3.348
_diffrn_reflns_theta_max         25.050
_diffrn_reflns_theta_full        25.050
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             10031
_reflns_number_gt                5033
_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0874P)²+35.6541P] 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         10031
_refine_ls_number_parameters     802
_refine_ls_number_restraints     30
_refine_ls_R_factor_all          0.1722
_refine_ls_R_factor_gt           0.0916
_refine_ls_wR_factor_ref         0.2717
_refine_ls_wR_factor_gt          0.2109
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_restrained_S_all      1.024
_refine_ls_shift/su_max          0.023
_refine_ls_shift/su_mean         0.001

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
Cd1 Cd -0.02952(9) 0.37555(5) 0.81982(4) 0.0623(3) Uani 1 1 d . . . . .
Cd2 Cd 0.33196(9) 0.38810(4) 0.72726(4) 0.0620(3) Uani 1 1 d . . . . .
Cd3 Cd 0.67992(10) 0.38954(6) 0.62736(5) 0.0873(4) Uani 1 1 d . . . . .
N1 N 0.4181(9) 0.3198(5) 0.7966(4) 0.060(3) Uani 1 1 d . . . . .
N2 N 0.2443(9) 0.3225(4) 0.6582(4) 0.059(3) Uani 1 1 d . . . . .
N3 N 0.6597(9) 0.4664(5) 0.6916(5) 0.066(3) Uani 1 1 d . . . . .
N4 N 0.0538(14) 0.4537(9) 0.8759(6) 0.123(4) Uani 1 1 d . U . . .
N5 N -0.0098(8) 0.4650(5) 0.7644(4) 0.060(3) Uani 1 1 d . . . . .
N6 N 0.3020(10) 0.4762(5) 0.6686(4) 0.065(3) Uani 1 1 d . . . . .
N7 N 0.3569(9) 0.4788(5) 0.7810(4) 0.064(3) Uani 1 1 d . . . . .
O1 O 0.1813(7) 0.3588(4) 0.7842(3) 0.062(2) Uani 1 1 d . . . . .
O2 O 0.1302(9) 0.3090(6) 0.8589(4) 0.104(4) Uani 1 1 d . . . . .
O3 O 0.2742(10) 0.1532(5) 1.0538(4) 0.105(4) Uani 1 1 d . . . . .
O4 O 0.3934(10) 0.0805(5) 1.0913(4) 0.102(3) Uani 1 1 d . . . . .
O5 O 0.4823(8) 0.3579(5) 0.6715(4) 0.082(3) Uani 1 1 d . . . . .
O6 O 0.5298(9) 0.3103(6) 0.5969(4) 0.118(4) Uani 1 1 d . U . . .
O7 O 0.2631(9) 0.0932(5) 0.3604(4) 0.098(3) Uani 1 1 d . . . . .
O8 O 0.3801(11) 0.1634(6) 0.3965(4) 0.109(4) Uani 1 1 d . . . . .
O9 O 0.6163(11) 0.4757(6) 0.5794(5) 0.118(4) Uani 1 1 d . . . . .
O10 O 0.5936(11) 0.5743(7) 0.5882(5) 0.120(4) Uani 1 1 d D . . . .
O11 O 0.7086(12) 0.8442(5) 0.8025(5) 0.118(4) Uani 1 1 d . . . . .
O12 O 0.5978(11) 0.7992(4) 0.7390(4) 0.096(3) Uani 1 1 d . . . . .
O13 O 0.094(2) 0.1881(10) 0.9771(7) 0.261(12) Uani 1 1 d . . . . .
O14 O 0.554(2) 0.5986(12) 0.4751(7) 0.342(17) Uani 1 1 d D . . . .
O15 O 0.0386(18) 0.3080(9) 0.9977(6) 0.208(8) Uani 1 1 d . . . . .
O16 O 0.8873(16) 0.2030(8) 0.8715(6) 0.178(6) Uani 1 1 d . . . . .
C1 C 0.2074(12) 0.3242(7) 0.8260(6) 0.069(4) Uani 1 1 d . . . . .
C2 C 0.3353(10) 0.2997(6) 0.8333(5) 0.055(3) Uani 1 1 d . . . . .
C3 C 0.5307(13) 0.2968(6) 0.8021(5) 0.067(3) Uani 1 1 d . . . . .
H3 H 0.5886 0.3096 0.7770 0.080 Uiso 1 1 calc R U . . .
C4 C 0.5663(11) 0.2549(6) 0.8433(5) 0.063(3) Uani 1 1 d . . . . .
H4 H 0.6465 0.2407 0.8456 0.075 Uiso 1 1 calc R U . . .
C5 C 0.4828(10) 0.2344(6) 0.8806(5) 0.054(3) Uani 1 1 d . . . . .
C6 C 0.3641(11) 0.2588(6) 0.8750(5) 0.059(3) Uani 1 1 d . . . . .
H6 H 0.3048 0.2469 0.8999 0.071 Uiso 1 1 calc R U . . .
C7 C 0.5121(10) 0.1879(6) 0.9247(4) 0.056(3) Uani 1 1 d . . . . .
C8 C 0.6136(12) 0.1500(8) 0.9217(6) 0.087(5) Uani 1 1 d . . . . .
H8 H 0.6674 0.1554 0.8928 0.104 Uiso 1 1 calc R U . . .
C9 C 0.6364(15) 0.1037(8) 0.9615(6) 0.105(6) Uani 1 1 d . . . . .
H9 H 0.7057 0.0791 0.9594 0.126 Uiso 1 1 calc R U . . .
C10 C 0.5553(13) 0.0945(7) 1.0042(6) 0.081(4) Uani 1 1 d . . . . .
H10 H 0.5697 0.0628 1.0297 0.098 Uiso 1 1 calc R U . . .
C11 C 0.4562(12) 0.1306(6) 1.0093(5) 0.062(3) Uani 1 1 d . . . . .
C12 C 0.3695(14) 0.1204(7) 1.0552(6) 0.076(4) Uani 1 1 d . . . . .
C13 C 0.4339(11) 0.1773(6) 0.9691(5) 0.058(3) Uani 1 1 d . . . . .
H13 H 0.3649 0.2020 0.9721 0.070 Uiso 1 1 calc R U . . .
C14 C 0.4528(14) 0.3250(10) 0.6295(7) 0.117(4) Uani 1 1 d . U . . .
C15 C 0.3256(10) 0.3024(6) 0.6210(4) 0.054(3) Uani 1 1 d . . . . .
C16 C 0.1279(11) 0.3051(6) 0.6504(5) 0.063(3) Uani 1 1 d . . . . .
H16 H 0.0704 0.3205 0.6745 0.076 Uiso 1 1 calc R U . . .
C17 C 0.0886(11) 0.2658(6) 0.6085(4) 0.060(3) Uani 1 1 d . . . . .
H17 H 0.0071 0.2536 0.6063 0.072 Uiso 1 1 calc R U . . .
C18 C 0.1707(10) 0.2436(5) 0.5689(4) 0.050(3) Uani 1 1 d . . . . .
C19 C 0.2928(11) 0.2642(6) 0.5778(4) 0.060(3) Uani 1 1 d . . . . .
H19 H 0.3522 0.2512 0.5536 0.072 Uiso 1 1 calc R U . . .
C20 C 0.1396(11) 0.1997(5) 0.5250(4) 0.050(3) Uani 1 1 d . . . . .
C21 C 0.0303(12) 0.1669(7) 0.5247(5) 0.072(4) Uani 1 1 d . . . . .
H21 H -0.0271 0.1754 0.5515 0.086 Uiso 1 1 calc R U . . .
C22 C 0.0061(14) 0.1218(8) 0.4847(6) 0.092(5) Uani 1 1 d . . . . .
H22 H -0.0664 0.0996 0.4855 0.111 Uiso 1 1 calc R U . . .
C23 C 0.0890(14) 0.1097(7) 0.4436(6) 0.086(5) Uani 1 1 d . . . . .
H23 H 0.0726 0.0789 0.4174 0.104 Uiso 1 1 calc R U . . .
C24 C 0.1931(11) 0.1423(6) 0.4416(4) 0.055(3) Uani 1 1 d . . . . .
C25 C 0.2826(15) 0.1317(8) 0.3976(6) 0.078(4) Uani 1 1 d . . . . .
C26 C 0.2189(10) 0.1869(5) 0.4819(4) 0.052(3) Uani 1 1 d . . . . .
H26 H 0.2914 0.2090 0.4801 0.063 Uiso 1 1 calc R U . . .
C27 C 0.6149(14) 0.5246(9) 0.6103(8) 0.093(5) Uani 1 1 d . . . . .
C28 C 0.6441(12) 0.5226(8) 0.6703(6) 0.075(4) Uani 1 1 d . . . . .
C29 C 0.6784(13) 0.4634(7) 0.7468(6) 0.077(4) Uani 1 1 d . . . . .
H29 H 0.6848 0.4244 0.7628 0.093 Uiso 1 1 calc R U . . .
C30 C 0.6889(12) 0.5120(7) 0.7811(6) 0.074(4) Uani 1 1 d . . . . .
H30 H 0.7041 0.5063 0.8193 0.089 Uiso 1 1 calc R U . . .
C31 C 0.6770(11) 0.5709(6) 0.7594(5) 0.061(3) Uani 1 1 d . . . . .
C32 C 0.6542(10) 0.5764(6) 0.7027(5) 0.062(3) Uani 1 1 d . . . . .
H32 H 0.6458 0.6150 0.6861 0.075 Uiso 1 1 calc R U . . .
C33 C 0.6976(13) 0.6242(6) 0.7935(6) 0.071(4) Uani 1 1 d . . . . .
C34 C 0.7443(14) 0.6204(7) 0.8493(6) 0.088(5) Uani 1 1 d . . . . .
H34 H 0.7624 0.5818 0.8642 0.105 Uiso 1 1 calc R U . . .
C35 C 0.7644(16) 0.6720(7) 0.8827(7) 0.097(5) Uani 1 1 d . . . . .
H35 H 0.7951 0.6678 0.9193 0.116 Uiso 1 1 calc R U . . .
C36 C 0.7377(13) 0.7306(7) 0.8607(6) 0.084(4) Uani 1 1 d . . . . .
H36 H 0.7493 0.7653 0.8829 0.101 Uiso 1 1 calc R U . . .
C37 C 0.6951(13) 0.7366(7) 0.8070(6) 0.074(4) Uani 1 1 d . . . . .
C38 C 0.6671(13) 0.7976(6) 0.7804(6) 0.069(4) Uani 1 1 d . . . . .
C39 C 0.6709(12) 0.6836(6) 0.7716(6) 0.074(4) Uani 1 1 d . . . . .
H39 H 0.6387 0.6884 0.7353 0.089 Uiso 1 1 calc R U . . .
C40 C 0.0961(15) 0.4508(10) 0.9292(6) 0.124(4) Uani 1 1 d . U . . .
H40 H 0.1059 0.4118 0.9447 0.149 Uiso 1 1 calc R U . . .
C41 C 0.1273(16) 0.5014(11) 0.9643(7) 0.126(4) Uani 1 1 d . U . . .
H41 H 0.1541 0.4964 1.0014 0.151 Uiso 1 1 calc R U . . .
C42 C 0.1150(16) 0.5590(11) 0.9395(7) 0.126(4) Uani 1 1 d . U . . .
H42 H 0.1303 0.5938 0.9613 0.151 Uiso 1 1 calc R U . . .
C43 C 0.0804(16) 0.5668(11) 0.8825(9) 0.118(7) Uani 1 1 d . . . . .
C44 C 0.0537(12) 0.5105(9) 0.8543(7) 0.089(5) Uani 1 1 d . . . . .
C45 C 0.072(2) 0.6247(11) 0.8545(13) 0.146(10) Uani 1 1 d . . . . .
H45 H 0.0829 0.6606 0.8753 0.175 Uiso 1 1 calc R U . . .
C46 C 0.0479(19) 0.6290(9) 0.8005(11) 0.126(7) Uani 1 1 d . . . . .
H46 H 0.0468 0.6676 0.7837 0.152 Uiso 1 1 calc R U . . .
C47 C 0.0232(13) 0.5747(7) 0.7664(9) 0.088(5) Uani 1 1 d . . . . .
C48 C 0.0218(10) 0.5167(6) 0.7945(7) 0.069(4) Uani 1 1 d . . . . .
C49 C -0.0004(14) 0.5754(8) 0.7097(10) 0.104(6) Uani 1 1 d . . . . .
H49 H 0.0003 0.6127 0.6907 0.124 Uiso 1 1 calc R U . . .
C50 C -0.0247(13) 0.5228(8) 0.6806(7) 0.085(4) Uani 1 1 d . . . . .
H50 H -0.0367 0.5236 0.6418 0.101 Uiso 1 1 calc R U . . .
C51 C -0.0311(11) 0.4670(6) 0.7104(6) 0.067(3) Uani 1 1 d . . . . .
H51 H -0.0509 0.4309 0.6912 0.080 Uiso 1 1 calc R U . . .
C52 C 0.2825(16) 0.4745(8) 0.6141(6) 0.099(5) Uani 1 1 d . . . . .
H52 H 0.2692 0.4365 0.5970 0.118 Uiso 1 1 calc R U . . .
C53 C 0.2809(17) 0.5270(10) 0.5811(8) 0.107(6) Uani 1 1 d . . . . .
H53 H 0.2684 0.5244 0.5425 0.129 Uiso 1 1 calc R U . . .
C54 C 0.2976(16) 0.5805(9) 0.6057(9) 0.109(6) Uani 1 1 d . . . . .
H54 H 0.2964 0.6158 0.5837 0.131 Uiso 1 1 calc R U . . .
C55 C 0.3174(12) 0.5866(7) 0.6644(7) 0.078(4) Uani 1 1 d . . . . .
C56 C 0.3225(11) 0.5298(6) 0.6942(6) 0.066(3) Uani 1 1 d . . . . .
C57 C 0.3413(15) 0.6414(8) 0.6939(9) 0.102(6) Uani 1 1 d . . . . .
H57 H 0.3431 0.6780 0.6738 0.122 Uiso 1 1 calc R U . . .
C58 C 0.3608(17) 0.6439(7) 0.7467(9) 0.105(6) Uani 1 1 d . . . . .
H58 H 0.3700 0.6820 0.7640 0.126 Uiso 1 1 calc R U . . .
C59 C 0.3687(14) 0.5895(8) 0.7795(8) 0.091(5) Uani 1 1 d . . . . .
C60 C 0.3498(11) 0.5333(6) 0.7534(6) 0.060(3) Uani 1 1 d . . . . .
C61 C 0.3900(16) 0.5862(9) 0.8390(9) 0.111(6) Uani 1 1 d . . . . .
H61 H 0.3977 0.6224 0.8595 0.133 Uiso 1 1 calc R U . . .
C62 C 0.3991(16) 0.5322(10) 0.8657(7) 0.105(6) Uani 1 1 d . . . . .
H62 H 0.4171 0.5310 0.9040 0.126 Uiso 1 1 calc R U . . .
C63 C 0.3817(13) 0.4785(7) 0.8361(6) 0.079(4) Uani 1 1 d . . . . .
H63 H 0.3874 0.4411 0.8549 0.095 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cd1 O8 2.275(9) 4_566 ?
Cd1 O12 2.284(9) 2_546 ?
Cd1 N4 2.330(16) . ?
Cd1 N5 2.366(10) . ?
Cd1 O2 2.430(9) . ?
Cd1 O1 2.513(8) . ?
Cd1 O7 2.588(10) 4_566 ?
Cd2 O5 2.250(9) . ?
Cd2 O1 2.264(8) . ?
Cd2 N2 2.359(9) . ?
Cd2 N7 2.363(10) . ?
Cd2 N6 2.388(10) . ?
Cd2 N1 2.394(10) . ?
Cd3 O11 2.264(13) 2_646 ?
Cd3 O3 2.268(10) 4_665 ?
Cd3 N3 2.283(11) . ?
Cd3 O9 2.291(13) . ?
Cd3 O6 2.472(11) . ?
Cd3 O5 2.533(9) . ?
Cd3 O4 2.601(10) 4_665 ?
Cd3 C12 2.751(16) 4_665 ?
N1 C3 1.331(15) . ?
N1 C2 1.354(14) . ?
N2 C16 1.336(14) . ?
N2 C15 1.350(14) . ?
N3 C29 1.329(16) . ?
N3 C28 1.332(17) . ?
N4 C40 1.341(19) . ?
N4 C44 1.34(2) . ?
N5 C51 1.305(15) . ?
N5 C48 1.371(15) . ?
N6 C52 1.314(16) . ?
N6 C56 1.330(15) . ?
N7 C63 1.335(15) . ?
N7 C60 1.355(15) . ?
O1 C1 1.275(14) . ?
O2 C1 1.220(15) . ?
O3 C12 1.262(17) . ?
O3 Cd3 2.268(10) 4_566 ?
O4 C12 1.246(16) . ?
O4 Cd3 2.601(10) 4_566 ?
O5 C14 1.266(17) . ?
O6 C14 1.209(16) . ?
O7 C25 1.235(15) . ?
O7 Cd1 2.588(10) 4_665 ?
O8 C25 1.271(17) . ?
O8 Cd1 2.275(9) 4_665 ?
O9 C27 1.29(2) . ?
O10 C27 1.220(18) . ?
O11 C38 1.222(16) . ?
O11 Cd3 2.264(13) 2_656 ?
O12 C38 1.225(15) . ?
O12 Cd1 2.284(9) 2_556 ?
C1 C2 1.502(16) . ?
C2 C6 1.365(16) . ?
C3 C4 1.387(17) . ?
C3 H3 0.9300 . ?
C4 C5 1.372(15) . ?
C4 H4 0.9300 . ?
C5 C6 1.404(15) . ?
C5 C7 1.487(16) . ?
C6 H6 0.9300 . ?
C7 C8 1.387(16) . ?
C7 C13 1.405(15) . ?
C8 C9 1.403(19) . ?
C8 H8 0.9300 . ?
C9 C10 1.388(19) . ?
C9 H9 0.9300 . ?
C10 C11 1.348(18) . ?
C10 H10 0.9300 . ?
C11 C13 1.412(16) . ?
C11 C12 1.492(18) . ?
C12 Cd3 2.751(16) 4_566 ?
C13 H13 0.9300 . ?
C14 C15 1.483(18) . ?
C15 C19 1.364(15) . ?
C16 C17 1.372(15) . ?
C16 H16 0.9300 . ?
C17 C18 1.413(14) . ?
C17 H17 0.9300 . ?
C18 C19 1.417(16) . ?
C18 C20 1.449(15) . ?
C19 H19 0.9300 . ?
C20 C21 1.391(16) . ?
C20 C26 1.399(15) . ?
C21 C22 1.387(18) . ?
C21 H21 0.9300 . ?
C22 C23 1.386(19) . ?
C22 H22 0.9300 . ?
C23 C24 1.343(18) . ?
C23 H23 0.9300 . ?
C24 C26 1.388(15) . ?
C24 C25 1.479(17) . ?
C26 H26 0.9300 . ?
C27 C28 1.46(2) . ?
C28 C32 1.405(19) . ?
C29 C30 1.341(18) . ?
C29 H29 0.9300 . ?
C30 C31 1.385(17) . ?
C30 H30 0.9300 . ?
C31 C32 1.373(16) . ?
C31 C33 1.430(18) . ?
C32 H32 0.9300 . ?
C33 C34 1.413(18) . ?
C33 C39 1.419(17) . ?
C34 C35 1.391(19) . ?
C34 H34 0.9300 . ?
C35 C36 1.403(18) . ?
C35 H35 0.9300 . ?
C36 C37 1.357(17) . ?
C36 H36 0.9300 . ?
C37 C39 1.447(18) . ?
C37 C38 1.496(18) . ?
C39 H39 0.9300 . ?
C40 C41 1.42(2) . ?
C40 H40 0.9300 . ?
C41 C42 1.39(3) . ?
C41 H41 0.9300 . ?
C42 C43 1.41(2) . ?
C42 H42 0.9300 . ?
C43 C45 1.43(3) . ?
C43 C44 1.42(2) . ?
C44 C48 1.46(2) . ?
C45 C46 1.31(3) . ?
C45 H45 0.9300 . ?
C46 C47 1.45(2) . ?
C46 H46 0.9300 . ?
C47 C49 1.37(2) . ?
C47 C48 1.43(2) . ?
C49 C50 1.36(2) . ?
C49 H49 0.9300 . ?
C50 C51 1.408(18) . ?
C50 H50 0.9300 . ?
C51 H51 0.9300 . ?
C52 C53 1.39(2) . ?
C52 H52 0.9300 . ?
C53 C54 1.31(2) . ?
C53 H53 0.9300 . ?
C54 C55 1.42(2) . ?
C54 H54 0.9300 . ?
C55 C57 1.40(2) . ?
C55 C56 1.426(18) . ?
C56 C60 1.437(18) . ?
C57 C58 1.27(2) . ?
C57 H57 0.9300 . ?
C58 C59 1.42(2) . ?
C58 H58 0.9300 . ?
C59 C60 1.384(18) . ?
C59 C61 1.43(2) . ?
C61 C62 1.34(2) . ?
C61 H61 0.9300 . ?
C62 C63 1.37(2) . ?
C62 H62 0.9300 . ?
C63 H63 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O8 Cd1 O12 94.8(4) 4_566 2_546 ?
O8 Cd1 N4 88.8(5) 4_566 . ?
O12 Cd1 N4 175.6(5) 2_546 . ?
O8 Cd1 N5 143.8(4) 4_566 . ?
O12 Cd1 N5 106.7(4) 2_546 . ?
N4 Cd1 N5 71.4(5) . . ?
O8 Cd1 O2 78.2(4) 4_566 . ?
O12 Cd1 O2 91.1(4) 2_546 . ?
N4 Cd1 O2 87.2(6) . . ?
N5 Cd1 O2 128.8(3) . . ?
O8 Cd1 O1 130.5(4) 4_566 . ?
O12 Cd1 O1 88.3(3) 2_546 . ?
N4 Cd1 O1 87.5(4) . . ?
N5 Cd1 O1 80.0(3) . . ?
O2 Cd1 O1 52.3(3) . . ?
O8 Cd1 O7 52.1(4) 4_566 4_566 ?
O12 Cd1 O7 98.6(4) 2_546 4_566 ?
N4 Cd1 O7 85.6(5) . 4_566 ?
N5 Cd1 O7 95.3(3) . 4_566 ?
O2 Cd1 O7 129.8(3) . 4_566 ?
O1 Cd1 O7 172.6(3) . 4_566 ?
O5 Cd2 O1 146.7(4) . . ?
O5 Cd2 N2 72.4(3) . . ?
O1 Cd2 N2 87.9(3) . . ?
O5 Cd2 N7 119.5(3) . . ?
O1 Cd2 N7 88.9(3) . . ?
N2 Cd2 N7 157.0(4) . . ?
O5 Cd2 N6 88.5(4) . . ?
O1 Cd2 N6 119.3(3) . . ?
N2 Cd2 N6 91.7(3) . . ?
N7 Cd2 N6 70.2(4) . . ?
O5 Cd2 N1 87.1(3) . . ?
O1 Cd2 N1 71.8(3) . . ?
N2 Cd2 N1 104.5(3) . . ?
N7 Cd2 N1 96.1(4) . . ?
N6 Cd2 N1 161.1(3) . . ?
O11 Cd3 O3 98.5(4) 2_646 4_665 ?
O11 Cd3 N3 83.3(4) 2_646 . ?
O3 Cd3 N3 151.4(4) 4_665 . ?
O11 Cd3 O9 150.8(4) 2_646 . ?
O3 Cd3 O9 94.9(4) 4_665 . ?
N3 Cd3 O9 72.8(4) . . ?
O11 Cd3 O6 104.5(4) 2_646 . ?
O3 Cd3 O6 78.6(4) 4_665 . ?
N3 Cd3 O6 128.9(3) . . ?
O9 Cd3 O6 103.6(4) . . ?
O11 Cd3 O5 91.1(4) 2_646 . ?
O3 Cd3 O5 129.0(4) 4_665 . ?
N3 Cd3 O5 79.3(3) . . ?
O9 Cd3 O5 100.4(4) . . ?
O6 Cd3 O5 50.7(3) . . ?
O11 Cd3 O4 83.5(4) 2_646 4_665 ?
O3 Cd3 O4 53.7(3) 4_665 4_665 ?
N3 Cd3 O4 98.5(3) . 4_665 ?
O9 Cd3 O4 83.7(4) . 4_665 ?
O6 Cd3 O4 132.2(3) . 4_665 ?
O5 Cd3 O4 174.4(3) . 4_665 ?
O11 Cd3 C12 91.8(4) 2_646 4_665 ?
O3 Cd3 C12 27.0(4) 4_665 4_665 ?
N3 Cd3 C12 124.8(4) . 4_665 ?
O9 Cd3 C12 88.5(4) . 4_665 ?
O6 Cd3 C12 105.6(4) . 4_665 ?
O5 Cd3 C12 155.9(4) . 4_665 ?
O4 Cd3 C12 26.7(3) 4_665 4_665 ?
C3 N1 C2 116.9(11) . . ?
C3 N1 Cd2 129.9(8) . . ?
C2 N1 Cd2 113.0(8) . . ?
C16 N2 C15 117.6(10) . . ?
C16 N2 Cd2 129.2(8) . . ?
C15 N2 Cd2 113.2(7) . . ?
C29 N3 C28 115.9(12) . . ?
C29 N3 Cd3 128.0(10) . . ?
C28 N3 Cd3 115.4(10) . . ?
C40 N4 C44 114.0(17) . . ?
C40 N4 Cd1 128.9(16) . . ?
C44 N4 Cd1 117.0(11) . . ?
C51 N5 C48 121.6(12) . . ?
C51 N5 Cd1 124.3(9) . . ?
C48 N5 Cd1 114.0(9) . . ?
C52 N6 C56 120.0(12) . . ?
C52 N6 Cd2 125.0(10) . . ?
C56 N6 Cd2 114.5(8) . . ?
C63 N7 C60 119.4(12) . . ?
C63 N7 Cd2 123.2(9) . . ?
C60 N7 Cd2 117.4(8) . . ?
C1 O1 Cd2 119.2(8) . . ?
C1 O1 Cd1 90.2(7) . . ?
Cd2 O1 Cd1 149.2(4) . . ?
C1 O2 Cd1 95.4(8) . . ?
C12 O3 Cd3 98.3(9) . 4_566 ?
C12 O4 Cd3 83.4(9) . 4_566 ?
C14 O5 Cd2 117.6(9) . . ?
C14 O5 Cd3 91.1(9) . . ?
Cd2 O5 Cd3 145.0(4) . . ?
C14 O6 Cd3 95.5(11) . . ?
C25 O7 Cd1 87.7(9) . 4_665 ?
C25 O8 Cd1 101.8(9) . 4_665 ?
C27 O9 Cd3 113.3(11) . . ?
C38 O11 Cd3 149.7(11) . 2_656 ?
C38 O12 Cd1 134.3(10) . 2_556 ?
O2 C1 O1 121.6(12) . . ?
O2 C1 C2 119.5(13) . . ?
O1 C1 C2 118.8(12) . . ?
N1 C2 C6 122.7(11) . . ?
N1 C2 C1 116.9(11) . . ?
C6 C2 C1 120.4(11) . . ?
N1 C3 C4 123.6(12) . . ?
N1 C3 H3 118.2 . . ?
C4 C3 H3 118.2 . . ?
C5 C4 C3 119.7(12) . . ?
C5 C4 H4 120.1 . . ?
C3 C4 H4 120.1 . . ?
C4 C5 C6 116.8(12) . . ?
C4 C5 C7 123.3(11) . . ?
C6 C5 C7 119.9(11) . . ?
C2 C6 C5 120.2(11) . . ?
C2 C6 H6 119.9 . . ?
C5 C6 H6 119.9 . . ?
C8 C7 C13 116.9(12) . . ?
C8 C7 C5 121.3(11) . . ?
C13 C7 C5 121.6(11) . . ?
C7 C8 C9 120.9(13) . . ?
C7 C8 H8 119.5 . . ?
C9 C8 H8 119.5 . . ?
C10 C9 C8 119.9(14) . . ?
C10 C9 H9 120.0 . . ?
C8 C9 H9 120.0 . . ?
C11 C10 C9 121.3(14) . . ?
C11 C10 H10 119.3 . . ?
C9 C10 H10 119.4 . . ?
C10 C11 C13 118.5(12) . . ?
C10 C11 C12 120.9(13) . . ?
C13 C11 C12 120.5(13) . . ?
O4 C12 O3 124.5(15) . . ?
O4 C12 C11 119.3(14) . . ?
O3 C12 C11 116.2(13) . . ?
O4 C12 Cd3 69.9(8) . 4_566 ?
O3 C12 Cd3 54.7(8) . 4_566 ?
C11 C12 Cd3 170.1(10) . 4_566 ?
C7 C13 C11 122.4(12) . . ?
C7 C13 H13 118.8 . . ?
C11 C13 H13 118.8 . . ?
O6 C14 O5 119.7(14) . . ?
O6 C14 C15 119.8(15) . . ?
O5 C14 C15 120.4(13) . . ?
N2 C15 C19 122.2(11) . . ?
N2 C15 C14 116.1(11) . . ?
C19 C15 C14 121.7(12) . . ?
N2 C16 C17 123.5(11) . . ?
N2 C16 H16 118.3 . . ?
C17 C16 H16 118.3 . . ?
C16 C17 C18 120.7(11) . . ?
C16 C17 H17 119.7 . . ?
C18 C17 H17 119.7 . . ?
C17 C18 C19 114.2(10) . . ?
C17 C18 C20 124.7(11) . . ?
C19 C18 C20 120.9(10) . . ?
C15 C19 C18 121.9(10) . . ?
C15 C19 H19 119.1 . . ?
C18 C19 H19 119.1 . . ?
C21 C20 C26 116.7(11) . . ?
C21 C20 C18 121.4(11) . . ?
C26 C20 C18 121.9(11) . . ?
C22 C21 C20 120.6(12) . . ?
C22 C21 H21 119.7 . . ?
C20 C21 H21 119.7 . . ?
C21 C22 C23 120.5(13) . . ?
C21 C22 H22 119.7 . . ?
C23 C22 H22 119.7 . . ?
C24 C23 C22 120.2(13) . . ?
C24 C23 H23 119.9 . . ?
C22 C23 H23 119.9 . . ?
C23 C24 C26 119.6(12) . . ?
C23 C24 C25 121.8(12) . . ?
C26 C24 C25 118.6(12) . . ?
O7 C25 O8 118.5(13) . . ?
O7 C25 C24 121.1(15) . . ?
O8 C25 C24 120.5(12) . . ?
C24 C26 C20 122.3(11) . . ?
C24 C26 H26 118.9 . . ?
C20 C26 H26 118.9 . . ?
O10 C27 O9 119.1(19) . . ?
O10 C27 C28 118.9(19) . . ?
O9 C27 C28 122.0(16) . . ?
N3 C28 C32 123.2(12) . . ?
N3 C28 C27 115.0(15) . . ?
C32 C28 C27 121.8(15) . . ?
N3 C29 C30 125.2(14) . . ?
N3 C29 H29 117.4 . . ?
C30 C29 H29 117.4 . . ?
C29 C30 C31 119.5(14) . . ?
C29 C30 H30 120.2 . . ?
C31 C30 H30 120.2 . . ?
C32 C31 C30 117.6(13) . . ?
C32 C31 C33 120.8(12) . . ?
C30 C31 C33 121.5(12) . . ?
C31 C32 C28 118.6(13) . . ?
C31 C32 H32 120.7 . . ?
C28 C32 H32 120.7 . . ?
C34 C33 C39 117.7(13) . . ?
C34 C33 C31 122.4(12) . . ?
C39 C33 C31 120.0(12) . . ?
C35 C34 C33 122.6(13) . . ?
C35 C34 H34 118.7 . . ?
C33 C34 H34 118.7 . . ?
C34 C35 C36 119.3(14) . . ?
C34 C35 H35 120.4 . . ?
C36 C35 H35 120.4 . . ?
C37 C36 C35 120.2(15) . . ?
C37 C36 H36 119.9 . . ?
C35 C36 H36 119.9 . . ?
C36 C37 C39 121.7(14) . . ?
C36 C37 C38 123.0(14) . . ?
C39 C37 C38 115.2(12) . . ?
O11 C38 O12 122.4(14) . . ?
O11 C38 C37 118.9(15) . . ?
O12 C38 C37 118.6(13) . . ?
C33 C39 C37 118.5(13) . . ?
C33 C39 H39 120.8 . . ?
C37 C39 H39 120.8 . . ?
N4 C40 C41 126(2) . . ?
N4 C40 H40 116.8 . . ?
C41 C40 H40 116.8 . . ?
C42 C41 C40 115.4(18) . . ?
C42 C41 H41 122.3 . . ?
C40 C41 H41 122.3 . . ?
C41 C42 C43 123(2) . . ?
C41 C42 H42 118.7 . . ?
C43 C42 H42 118.7 . . ?
C42 C43 C45 125(2) . . ?
C42 C43 C44 113(2) . . ?
C45 C43 C44 122(2) . . ?
N4 C44 C43 127.7(19) . . ?
N4 C44 C48 117.4(14) . . ?
C43 C44 C48 114.9(19) . . ?
C46 C45 C43 122(2) . . ?
C46 C45 H45 118.9 . . ?
C43 C45 H45 118.9 . . ?
C45 C46 C47 121(2) . . ?
C45 C46 H46 119.3 . . ?
C47 C46 H46 119.3 . . ?
C49 C47 C48 118.0(15) . . ?
C49 C47 C46 124.8(19) . . ?
C48 C47 C46 117.1(18) . . ?
N5 C48 C47 118.9(14) . . ?
N5 C48 C44 118.8(13) . . ?
C47 C48 C44 122.3(15) . . ?
C50 C49 C47 121.6(16) . . ?
C50 C49 H49 119.2 . . ?
C47 C49 H49 119.2 . . ?
C49 C50 C51 118.4(16) . . ?
C49 C50 H50 120.8 . . ?
C51 C50 H50 120.8 . . ?
N5 C51 C50 121.3(14) . . ?
N5 C51 H51 119.4 . . ?
C50 C51 H51 119.4 . . ?
N6 C52 C53 122.6(16) . . ?
N6 C52 H52 118.7 . . ?
C53 C52 H52 118.7 . . ?
C54 C53 C52 118.3(17) . . ?
C54 C53 H53 120.8 . . ?
C52 C53 H53 120.8 . . ?
C53 C54 C55 122.7(17) . . ?
C53 C54 H54 118.6 . . ?
C55 C54 H54 118.6 . . ?
C57 C55 C54 126.6(16) . . ?
C57 C55 C56 118.7(15) . . ?
C54 C55 C56 114.5(15) . . ?
N6 C56 C55 121.7(13) . . ?
N6 C56 C60 121.7(12) . . ?
C55 C56 C60 116.7(13) . . ?
C58 C57 C55 123.7(16) . . ?
C58 C57 H57 118.1 . . ?
C55 C57 H57 118.1 . . ?
C57 C58 C59 121.2(17) . . ?
C57 C58 H58 119.4 . . ?
C59 C58 H58 119.4 . . ?
C60 C59 C58 118.7(16) . . ?
C60 C59 C61 114.7(16) . . ?
C58 C59 C61 126.5(16) . . ?
N7 C60 C59 123.1(14) . . ?
N7 C60 C56 116.0(11) . . ?
C59 C60 C56 120.8(14) . . ?
C62 C61 C59 121.6(16) . . ?
C62 C61 H61 119.2 . . ?
C59 C61 H61 119.2 . . ?
C61 C62 C63 119.5(17) . . ?
C61 C62 H62 120.3 . . ?
C63 C62 H62 120.2 . . ?
N7 C63 C62 121.5(16) . . ?
N7 C63 H63 119.2 . . ?
C62 C63 H63 119.2 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cd1 O2 C1 O1 -7.4(15) . . . . ?
Cd1 O2 C1 C2 175.3(10) . . . . ?
Cd2 O1 C1 O2 177.4(11) . . . . ?
Cd1 O1 C1 O2 7.1(15) . . . . ?
Cd2 O1 C1 C2 -5.3(15) . . . . ?
Cd1 O1 C1 C2 -175.5(11) . . . . ?
C3 N1 C2 C6 1.2(17) . . . . ?
Cd2 N1 C2 C6 177.7(9) . . . . ?
C3 N1 C2 C1 -178.3(11) . . . . ?
Cd2 N1 C2 C1 -1.8(13) . . . . ?
O2 C1 C2 N1 -177.9(13) . . . . ?
O1 C1 C2 N1 4.7(17) . . . . ?
O2 C1 C2 C6 3(2) . . . . ?
O1 C1 C2 C6 -174.8(11) . . . . ?
C2 N1 C3 C4 -0.8(18) . . . . ?
Cd2 N1 C3 C4 -176.7(9) . . . . ?
N1 C3 C4 C5 0.8(19) . . . . ?
C3 C4 C5 C6 -1.0(17) . . . . ?
C3 C4 C5 C7 177.8(11) . . . . ?
N1 C2 C6 C5 -1.5(18) . . . . ?
C1 C2 C6 C5 178.0(11) . . . . ?
C4 C5 C6 C2 1.4(17) . . . . ?
C7 C5 C6 C2 -177.4(10) . . . . ?
C4 C5 C7 C8 -17.9(18) . . . . ?
C6 C5 C7 C8 160.8(12) . . . . ?
C4 C5 C7 C13 166.6(11) . . . . ?
C6 C5 C7 C13 -14.7(17) . . . . ?
C13 C7 C8 C9 0(2) . . . . ?
C5 C7 C8 C9 -176.0(14) . . . . ?
C7 C8 C9 C10 1(3) . . . . ?
C8 C9 C10 C11 -2(3) . . . . ?
C9 C10 C11 C13 2(2) . . . . ?
C9 C10 C11 C12 180.0(14) . . . . ?
Cd3 O4 C12 O3 2.9(15) 4_566 . . . ?
Cd3 O4 C12 C11 -175.9(12) 4_566 . . . ?
Cd3 O3 C12 O4 -3.3(17) 4_566 . . . ?
Cd3 O3 C12 C11 175.5(9) 4_566 . . . ?
C10 C11 C12 O4 5(2) . . . . ?
C13 C11 C12 O4 -177.4(12) . . . . ?
C10 C11 C12 O3 -174.3(13) . . . . ?
C13 C11 C12 O3 3.7(19) . . . . ?
C8 C7 C13 C11 0.1(18) . . . . ?
C5 C7 C13 C11 175.8(10) . . . . ?
C10 C11 C13 C7 -0.9(18) . . . . ?
C12 C11 C13 C7 -179.0(11) . . . . ?
Cd3 O6 C14 O5 -18(2) . . . . ?
Cd3 O6 C14 C15 164.7(16) . . . . ?
Cd2 O5 C14 O6 176.4(16) . . . . ?
Cd3 O5 C14 O6 17(2) . . . . ?
Cd2 O5 C14 C15 -6(2) . . . . ?
Cd3 O5 C14 C15 -165.2(17) . . . . ?
C16 N2 C15 C19 -2.2(18) . . . . ?
Cd2 N2 C15 C19 -179.9(9) . . . . ?
C16 N2 C15 C14 177.2(14) . . . . ?
Cd2 N2 C15 C14 -0.5(15) . . . . ?
O6 C14 C15 N2 -178.1(17) . . . . ?
O5 C14 C15 N2 4(3) . . . . ?
O6 C14 C15 C19 1(3) . . . . ?
O5 C14 C15 C19 -176.3(15) . . . . ?
C15 N2 C16 C17 3.5(19) . . . . ?
Cd2 N2 C16 C17 -179.3(9) . . . . ?
N2 C16 C17 C18 -3(2) . . . . ?
C16 C17 C18 C19 1.7(17) . . . . ?
C16 C17 C18 C20 176.7(11) . . . . ?
N2 C15 C19 C18 0.9(19) . . . . ?
C14 C15 C19 C18 -178.5(14) . . . . ?
C17 C18 C19 C15 -0.6(17) . . . . ?
C20 C18 C19 C15 -175.8(11) . . . . ?
C17 C18 C20 C21 -11.9(18) . . . . ?
C19 C18 C20 C21 162.8(12) . . . . ?
C17 C18 C20 C26 169.8(11) . . . . ?
C19 C18 C20 C26 -15.5(16) . . . . ?
C26 C20 C21 C22 3.2(19) . . . . ?
C18 C20 C21 C22 -175.2(12) . . . . ?
C20 C21 C22 C23 -2(2) . . . . ?
C21 C22 C23 C24 -1(2) . . . . ?
C22 C23 C24 C26 2(2) . . . . ?
C22 C23 C24 C25 -178.6(14) . . . . ?
Cd1 O7 C25 O8 1.0(15) 4_665 . . . ?
Cd1 O7 C25 C24 179.2(13) 4_665 . . . ?
Cd1 O8 C25 O7 -1.2(18) 4_665 . . . ?
Cd1 O8 C25 C24 -179.4(11) 4_665 . . . ?
C23 C24 C25 O7 2(2) . . . . ?
C26 C24 C25 O7 -179.0(13) . . . . ?
C23 C24 C25 O8 179.8(15) . . . . ?
C26 C24 C25 O8 -1(2) . . . . ?
C23 C24 C26 C20 -0.3(19) . . . . ?
C25 C24 C26 C20 -179.7(11) . . . . ?
C21 C20 C26 C24 -2.3(17) . . . . ?
C18 C20 C26 C24 176.1(10) . . . . ?
Cd3 O9 C27 O10 173.2(12) . . . . ?
Cd3 O9 C27 C28 -3.7(19) . . . . ?
C29 N3 C28 C32 4.1(19) . . . . ?
Cd3 N3 C28 C32 -167.0(10) . . . . ?
C29 N3 C28 C27 -175.8(12) . . . . ?
Cd3 N3 C28 C27 13.2(15) . . . . ?
O10 C27 C28 N3 176.6(14) . . . . ?
O9 C27 C28 N3 -6(2) . . . . ?
O10 C27 C28 C32 -3(2) . . . . ?
O9 C27 C28 C32 173.6(14) . . . . ?
C28 N3 C29 C30 -4(2) . . . . ?
Cd3 N3 C29 C30 166.0(11) . . . . ?
N3 C29 C30 C31 2(2) . . . . ?
C29 C30 C31 C32 0(2) . . . . ?
C29 C30 C31 C33 -174.7(13) . . . . ?
C30 C31 C32 C28 0.2(18) . . . . ?
C33 C31 C32 C28 175.1(12) . . . . ?
N3 C28 C32 C31 -2.5(19) . . . . ?
C27 C28 C32 C31 177.4(12) . . . . ?
C32 C31 C33 C34 -167.4(13) . . . . ?
C30 C31 C33 C34 7(2) . . . . ?
C32 C31 C33 C39 13(2) . . . . ?
C30 C31 C33 C39 -172.7(12) . . . . ?
C39 C33 C34 C35 0(2) . . . . ?
C31 C33 C34 C35 -179.9(15) . . . . ?
C33 C34 C35 C36 0(3) . . . . ?
C34 C35 C36 C37 -1(2) . . . . ?
C35 C36 C37 C39 3(2) . . . . ?
C35 C36 C37 C38 -178.8(14) . . . . ?
Cd3 O11 C38 O12 175.3(14) 2_656 . . . ?
Cd3 O11 C38 C37 -1(3) 2_656 . . . ?
Cd1 O12 C38 O11 7(2) 2_556 . . . ?
Cd1 O12 C38 C37 -176.9(9) 2_556 . . . ?
C36 C37 C38 O11 17(2) . . . . ?
C39 C37 C38 O11 -164.4(13) . . . . ?
C36 C37 C38 O12 -159.2(14) . . . . ?
C39 C37 C38 O12 19.5(19) . . . . ?
C34 C33 C39 C37 1(2) . . . . ?
C31 C33 C39 C37 -178.9(12) . . . . ?
C36 C37 C39 C33 -3(2) . . . . ?
C38 C37 C39 C33 178.7(12) . . . . ?
C44 N4 C40 C41 7(3) . . . . ?
Cd1 N4 C40 C41 -168.9(13) . . . . ?
N4 C40 C41 C42 -2(3) . . . . ?
C40 C41 C42 C43 -3(3) . . . . ?
C41 C42 C43 C45 -177(2) . . . . ?
C41 C42 C43 C44 3(3) . . . . ?
C40 N4 C44 C43 -7(3) . . . . ?
Cd1 N4 C44 C43 168.9(12) . . . . ?
C40 N4 C44 C48 173.4(12) . . . . ?
Cd1 N4 C44 C48 -10.5(18) . . . . ?
C42 C43 C44 N4 3(3) . . . . ?
C45 C43 C44 N4 -177.2(18) . . . . ?
C42 C43 C44 C48 -177.8(13) . . . . ?
C45 C43 C44 C48 2(2) . . . . ?
C42 C43 C45 C46 175(2) . . . . ?
C44 C43 C45 C46 -5(3) . . . . ?
C43 C45 C46 C47 3(4) . . . . ?
C45 C46 C47 C49 -179(2) . . . . ?
C45 C46 C47 C48 2(3) . . . . ?
C51 N5 C48 C47 4.3(17) . . . . ?
Cd1 N5 C48 C47 -173.2(9) . . . . ?
C51 N5 C48 C44 -175.3(11) . . . . ?
Cd1 N5 C48 C44 7.2(13) . . . . ?
C49 C47 C48 N5 -4(2) . . . . ?
C46 C47 C48 N5 175.3(13) . . . . ?
C49 C47 C48 C44 175.9(13) . . . . ?
C46 C47 C48 C44 -5(2) . . . . ?
N4 C44 C48 N5 2.0(19) . . . . ?
C43 C44 C48 N5 -177.5(12) . . . . ?
N4 C44 C48 C47 -177.6(14) . . . . ?
C43 C44 C48 C47 2.9(19) . . . . ?
C48 C47 C49 C50 0(2) . . . . ?
C46 C47 C49 C50 -178.9(16) . . . . ?
C47 C49 C50 C51 3(2) . . . . ?
C48 N5 C51 C50 -1.2(18) . . . . ?
Cd1 N5 C51 C50 176.1(9) . . . . ?
C49 C50 C51 N5 -3(2) . . . . ?
C56 N6 C52 C53 -1(2) . . . . ?
Cd2 N6 C52 C53 -171.7(13) . . . . ?
N6 C52 C53 C54 -1(3) . . . . ?
C52 C53 C54 C55 0(3) . . . . ?
C53 C54 C55 C57 177.0(18) . . . . ?
C53 C54 C55 C56 2(2) . . . . ?
C52 N6 C56 C55 3(2) . . . . ?
Cd2 N6 C56 C55 175.4(9) . . . . ?
C52 N6 C56 C60 -177.1(13) . . . . ?
Cd2 N6 C56 C60 -5.1(15) . . . . ?
C57 C55 C56 N6 -179.3(13) . . . . ?
C54 C55 C56 N6 -4(2) . . . . ?
C57 C55 C56 C60 1.3(19) . . . . ?
C54 C55 C56 C60 176.3(12) . . . . ?
C54 C55 C57 C58 -178.5(18) . . . . ?
C56 C55 C57 C58 -4(3) . . . . ?
C55 C57 C58 C59 5(3) . . . . ?
C57 C58 C59 C60 -3(3) . . . . ?
C57 C58 C59 C61 -179.9(18) . . . . ?
C63 N7 C60 C59 0.9(19) . . . . ?
Cd2 N7 C60 C59 -176.7(10) . . . . ?
C63 N7 C60 C56 -179.9(11) . . . . ?
Cd2 N7 C60 C56 2.6(14) . . . . ?
C58 C59 C60 N7 179.1(13) . . . . ?
C61 C59 C60 N7 -3(2) . . . . ?
C58 C59 C60 C56 0(2) . . . . ?
C61 C59 C60 C56 177.5(13) . . . . ?
N6 C56 C60 N7 1.8(18) . . . . ?
C55 C56 C60 N7 -178.7(11) . . . . ?
N6 C56 C60 C59 -178.9(12) . . . . ?
C55 C56 C60 C59 0.6(19) . . . . ?
C60 C59 C61 C62 4(3) . . . . ?
C58 C59 C61 C62 -178.1(18) . . . . ?
C59 C61 C62 C63 -3(3) . . . . ?
C60 N7 C63 C62 1(2) . . . . ?
Cd2 N7 C63 C62 178.1(11) . . . . ?
C61 C62 C63 N7 1(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C51 H51 O11 0.93 2.56 3.308(18) 137.5 2_546
C51 H51 O4 0.93 2.46 3.111(18) 127.6 4_565
C32 H32 O16 0.93 2.38 3.29(2) 169.2 2_656
C30 H30 O7 0.93 2.45 3.059(17) 123.1 4_666
C29 H29 O11 0.93 2.64 3.117(18) 112.6 2_646
C29 H29 O7 0.93 2.49 3.092(18) 123.0 4_666
C51 H51 O11 0.93 2.56 3.308(18) 137.5 2_546
C51 H51 O4 0.93 2.46 3.111(18) 127.6 4_565
C32 H32 O16 0.93 2.38 3.29(2) 169.2 2_656
C30 H30 O7 0.93 2.45 3.059(17) 123.1 4_666
C29 H29 O11 0.93 2.64 3.117(18) 112.6 2_646
C29 H29 O7 0.93 2.49 3.092(18) 123.0 4_666
C29 H29 O7 0.93 2.49 3.092(18) 123.0 4_666
C29 H29 O11 0.93 2.64 3.117(18) 112.6 2_646
C30 H30 O7 0.93 2.45 3.059(17) 123.1 4_666
C32 H32 O16 0.93 2.38 3.29(2) 169.2 2_656
C51 H51 O4 0.93 2.46 3.111(18) 127.6 4_565
C51 H51 O11 0.93 2.56 3.308(18) 137.5 2_546

_refine_diff_density_max         1.770
_refine_diff_density_min         -1.716
_refine_diff_density_rms         0.122

