# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2022

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

data_2
_database_code_depnum_ccdc_archive 'CCDC 2112368'
loop_
_audit_author_name
_audit_author_address
'Petr Primakov'
;A N Nesmeyanov Institute of Organoelement Compounds of Russian Academy of Sciences
Russia
;
_audit_update_record             
;
2021-10-11 deposited with the CCDC.	2022-02-04 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            'C30 H24 N4 O12 Zn2'
_chemical_formula_weight         763.27

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

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

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

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

_cell_length_a                   8.3911(4)
_cell_length_b                   9.9264(4)
_cell_length_c                   10.7162(5)
_cell_angle_alpha                63.7920(10)
_cell_angle_beta                 74.0280(10)
_cell_angle_gamma                73.3250(10)
_cell_volume                     755.62(6)
_cell_formula_units_Z            1
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    4412
_cell_measurement_theta_min      2.47
_cell_measurement_theta_max      30.63

_exptl_crystal_description       prizm
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.677
_exptl_crystal_F_000             388
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    1.661
_shelx_estimated_absorpt_T_min   0.801
_shelx_estimated_absorpt_T_max   0.852
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3166
_exptl_absorpt_correction_T_max  0.3813
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9479
_diffrn_reflns_av_unetI/netI     0.0299
_diffrn_reflns_av_R_equivalents  0.0223
_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       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.151
_diffrn_reflns_theta_max         28.996
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4012
_reflns_number_gt                3533
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0378P)²+0.2564P] 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         4012
_refine_ls_number_parameters     257
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0349
_refine_ls_R_factor_gt           0.0288
_refine_ls_wR_factor_ref         0.0728
_refine_ls_wR_factor_gt          0.0697
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.035
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Zn1 Zn 0.15791(2) 0.40755(2) 0.44622(2) 0.01922(7) Uani 1 1 d . . . . .
N1 N 0.36548(18) 0.27109(16) 0.38535(15) 0.0203(3) Uani 1 1 d . . . . .
N2 N 0.80837(19) 0.1223(2) 0.43053(18) 0.0296(4) Uani 1 1 d . . . . .
H21 H 0.8975 0.0700 0.3885 0.035 Uiso 1 1 d R U . . .
H22 H 0.8162 0.1904 0.4583 0.035 Uiso 1 1 d R U . . .
O1 O 0.0130(10) 0.5931(19) 0.6630(12) 0.0258(17) Uani 0.54(4) 1 d . . P A 1
O1' O -0.0084(8) 0.536(2) 0.6904(9) 0.019(2) Uani 0.46(4) 1 d . . P A 2
O2 O 0.2421(8) 0.4580(18) 0.5717(16) 0.0235(19) Uani 0.50(4) 1 d . . P A 1
O2' O 0.2175(11) 0.4064(15) 0.6223(17) 0.0234(19) Uani 0.50(4) 1 d . . P A 2
O3 O 0.14471(17) 0.5343(2) 0.88746(15) 0.0373(4) Uani 1 1 d . . . . .
O4 O 0.1762(7) 0.6193(4) 0.2847(8) 0.0217(15) Uani 0.51(2) 1 d . . P A 1
O4' O 0.2042(5) 0.6298(4) 0.3364(10) 0.0250(19) Uani 0.49(2) 1 d . . P A 2
O5 O 0.000(3) 0.7514(15) 0.4086(13) 0.017(2) Uani 0.39(6) 1 d . . P A 1
O5' O -0.049(3) 0.7639(7) 0.3873(15) 0.029(2) Uani 0.61(6) 1 d . . P A 2
O6 O 0.0610(2) 1.02283(15) 0.19655(16) 0.0388(4) Uani 1 1 d . . . . .
C1 C 0.1490(2) 0.49387(19) 0.67889(18) 0.0212(3) Uani 1 1 d . . . . .
C2 C 0.2351(2) 0.47788(19) 0.78862(19) 0.0219(3) Uani 1 1 d . . . . .
C3 C 0.2496(3) 0.4992(3) 0.9789(2) 0.0378(5) Uani 1 1 d . . . . .
H3 H 0.2194 0.5245 1.0592 0.045 Uiso 1 1 calc R U . . .
C4 C 0.4011(3) 0.4241(2) 0.9398(3) 0.0342(5) Uani 1 1 d . . . . .
H4 H 0.4959 0.3873 0.9861 0.041 Uiso 1 1 calc R U . . .
C5 C 0.3929(3) 0.4102(2) 0.8161(3) 0.0341(5) Uani 1 1 d . . . . .
H5 H 0.4811 0.3626 0.7628 0.041 Uiso 1 1 calc R U . . .
C6 C 0.0976(2) 0.7460(2) 0.30844(19) 0.0224(3) Uani 1 1 d . . . . .
C7 C 0.1436(2) 0.88680(19) 0.18880(19) 0.0224(3) Uani 1 1 d . . . . .
C8 C 0.1178(3) 1.1342(2) 0.0724(2) 0.0362(5) Uani 1 1 d . . . . .
H8 H 0.0813 1.2409 0.0495 0.043 Uiso 1 1 calc R U . . .
C9 C 0.2305(3) 1.0731(2) -0.0114(2) 0.0426(6) Uani 1 1 d . . . . .
H9 H 0.2869 1.1255 -0.1037 0.051 Uiso 1 1 calc R U . . .
C10 C 0.2490(4) 0.9121(2) 0.0663(3) 0.0595(9) Uani 1 1 d . . . . .
H10 H 0.3237 0.8361 0.0359 0.071 Uiso 1 1 calc R U . . .
C11 C 0.5156(2) 0.24926(19) 0.42048(18) 0.0212(3) Uani 1 1 d . . . . .
H11 H 0.5256 0.3050 0.4698 0.025 Uiso 1 1 calc R U . . .
C12 C 0.6580(2) 0.1474(2) 0.38713(18) 0.0218(3) Uani 1 1 d . . . . .
C13 C 0.6386(2) 0.0668(2) 0.3153(2) 0.0259(4) Uani 1 1 d . . . . .
H13 H 0.7313 -0.0041 0.2913 0.031 Uiso 1 1 calc R U . . .
C14 C 0.4837(2) 0.0907(2) 0.2793(2) 0.0280(4) Uani 1 1 d . . . . .
H14 H 0.4697 0.0368 0.2298 0.034 Uiso 1 1 calc R U . . .
C15 C 0.3489(2) 0.1936(2) 0.31571(19) 0.0245(4) Uani 1 1 d . . . . .
H15 H 0.2427 0.2094 0.2908 0.029 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 O2 1.969(4) . ?
Zn1 O1' 1.977(5) 2_566 ?
Zn1 N1 2.0237(14) . ?
Zn1 O5' 2.054(6) 2_566 ?
Zn1 O4 2.064(3) . ?
Zn1 O2' 2.076(8) . ?
Zn1 O4' 2.085(4) . ?
Zn1 O1 2.089(7) 2_566 ?
Zn1 O5 2.135(10) 2_566 ?
Zn1 Zn1 3.0193(4) 2_566 ?
N1 C15 1.340(2) . ?
N1 C11 1.344(2) . ?
N2 C12 1.382(2) . ?
N2 H21 0.9111 . ?
N2 H22 0.8739 . ?
O1 C1 1.271(5) . ?
O1 Zn1 2.089(7) 2_566 ?
O1' C1 1.254(5) . ?
O1' Zn1 1.977(5) 2_566 ?
O2 C1 1.329(8) . ?
O2' C1 1.199(4) . ?
O3 C2 1.360(2) . ?
O3 C3 1.361(2) . ?
O4 C6 1.340(5) . ?
O4' C6 1.213(3) . ?
O5 C6 1.170(10) . ?
O5 Zn1 2.135(10) 2_566 ?
O5' C6 1.304(12) . ?
O5' Zn1 2.054(6) 2_566 ?
O6 C7 1.357(2) . ?
O6 C8 1.369(2) . ?
C1 C2 1.472(2) . ?
C2 C5 1.349(2) . ?
C3 C4 1.336(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.414(3) . ?
C4 H4 0.9500 . ?
C5 H5 0.9500 . ?
C6 C7 1.483(2) . ?
C7 C10 1.329(3) . ?
C8 C9 1.324(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.422(3) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
C11 C12 1.404(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.395(3) . ?
C13 C14 1.384(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.386(3) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 Zn1 N1 101.29(12) . . ?
O1' Zn1 N1 104.3(2) 2_566 . ?
O1' Zn1 O5' 99.5(10) 2_566 2_566 ?
N1 Zn1 O5' 96.9(3) . 2_566 ?
O2 Zn1 O4 91.9(6) . . ?
N1 Zn1 O4 102.26(10) . . ?
O1' Zn1 O2' 153.9(2) 2_566 . ?
N1 Zn1 O2' 101.75(13) . . ?
O5' Zn1 O2' 76.0(9) 2_566 . ?
O1' Zn1 O4' 86.1(7) 2_566 . ?
N1 Zn1 O4' 105.93(12) . . ?
O5' Zn1 O4' 154.4(3) 2_566 . ?
O2' Zn1 O4' 88.0(6) . . ?
O2 Zn1 O1 158.18(17) . 2_566 ?
N1 Zn1 O1 100.53(13) . 2_566 ?
O4 Zn1 O1 83.6(6) . 2_566 ?
O2 Zn1 O5 102.7(7) . 2_566 ?
N1 Zn1 O5 102.7(5) . 2_566 ?
O4 Zn1 O5 147.9(8) . 2_566 ?
O1 Zn1 O5 72.2(8) 2_566 2_566 ?
O2 Zn1 Zn1 78.58(11) . 2_566 ?
O1' Zn1 Zn1 76.9(2) 2_566 2_566 ?
N1 Zn1 Zn1 176.19(4) . 2_566 ?
O5' Zn1 Zn1 79.3(3) 2_566 2_566 ?
O4 Zn1 Zn1 81.55(9) . 2_566 ?
O2' Zn1 Zn1 77.02(14) . 2_566 ?
O4' Zn1 Zn1 77.70(12) . 2_566 ?
O1 Zn1 Zn1 79.63(11) 2_566 2_566 ?
O5 Zn1 Zn1 73.7(5) 2_566 2_566 ?
C15 N1 C11 119.57(15) . . ?
C15 N1 Zn1 118.45(12) . . ?
C11 N1 Zn1 121.84(12) . . ?
C12 N2 H21 113.6 . . ?
C12 N2 H22 115.0 . . ?
H21 N2 H22 124.4 . . ?
C1 O1 Zn1 120.6(6) . 2_566 ?
C1 O1' Zn1 130.2(3) . 2_566 ?
C1 O2 Zn1 125.8(5) . . ?
C1 O2' Zn1 126.4(5) . . ?
C2 O3 C3 106.43(16) . . ?
C6 O4 Zn1 119.4(4) . . ?
C6 O4' Zn1 125.8(3) . . ?
C6 O5 Zn1 128.9(5) . 2_566 ?
C6 O5' Zn1 125.9(6) . 2_566 ?
C7 O6 C8 106.53(15) . . ?
O2' C1 O1' 118.4(8) . . ?
O1 C1 O2 120.5(6) . . ?
O2' C1 C2 113.6(3) . . ?
O1' C1 C2 120.1(3) . . ?
O1 C1 C2 115.5(3) . . ?
O2 C1 C2 118.0(2) . . ?
C5 C2 O3 109.98(17) . . ?
C5 C2 C1 131.95(18) . . ?
O3 C2 C1 118.03(15) . . ?
C4 C3 O3 110.5(2) . . ?
C4 C3 H3 124.8 . . ?
O3 C3 H3 124.8 . . ?
C3 C4 C5 106.62(18) . . ?
C3 C4 H4 126.7 . . ?
C5 C4 H4 126.7 . . ?
C2 C5 C4 106.49(18) . . ?
C2 C5 H5 126.8 . . ?
C4 C5 H5 126.8 . . ?
O4' C6 O5' 124.7(6) . . ?
O5 C6 O4 126.1(6) . . ?
O5 C6 C7 121.5(6) . . ?
O4' C6 C7 118.8(2) . . ?
O5' C6 C7 115.8(4) . . ?
O4 C6 C7 112.4(2) . . ?
C10 C7 O6 109.20(16) . . ?
C10 C7 C6 133.41(17) . . ?
O6 C7 C6 117.34(15) . . ?
C9 C8 O6 110.88(17) . . ?
C9 C8 H8 124.6 . . ?
O6 C8 H8 124.6 . . ?
C8 C9 C10 105.30(19) . . ?
C8 C9 H9 127.4 . . ?
C10 C9 H9 127.4 . . ?
C7 C10 C9 108.06(18) . . ?
C7 C10 H10 126.0 . . ?
C9 C10 H10 126.0 . . ?
N1 C11 C12 122.59(17) . . ?
N1 C11 H11 118.7 . . ?
C12 C11 H11 118.7 . . ?
N2 C12 C13 121.57(16) . . ?
N2 C12 C11 121.12(17) . . ?
C13 C12 C11 117.22(16) . . ?
C14 C13 C12 119.63(17) . . ?
C14 C13 H13 120.2 . . ?
C12 C13 H13 120.2 . . ?
C13 C14 C15 119.76(18) . . ?
C13 C14 H14 120.1 . . ?
C15 C14 H14 120.1 . . ?
N1 C15 C14 121.22(17) . . ?
N1 C15 H15 119.4 . . ?
C14 C15 H15 119.4 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Zn1 O2' C1 O1' 39.2(19) . . . . ?
Zn1 O2' C1 C2 -171.6(9) . . . . ?
Zn1 O1' C1 O2' -41(2) 2_566 . . . ?
Zn1 O1' C1 C2 171.4(11) 2_566 . . . ?
Zn1 O1 C1 O2 44.0(17) 2_566 . . . ?
Zn1 O1 C1 C2 -163.7(6) 2_566 . . . ?
Zn1 O2 C1 O1 -48.5(19) . . . . ?
Zn1 O2 C1 C2 159.9(8) . . . . ?
C3 O3 C2 C5 -0.5(2) . . . . ?
C3 O3 C2 C1 177.31(16) . . . . ?
O2' C1 C2 C5 17.4(10) . . . . ?
O1' C1 C2 C5 166.0(11) . . . . ?
O1 C1 C2 C5 -164.8(10) . . . . ?
O2 C1 C2 C5 -11.8(9) . . . . ?
O2' C1 C2 O3 -159.8(10) . . . . ?
O1' C1 C2 O3 -11.2(11) . . . . ?
O1 C1 C2 O3 18.0(10) . . . . ?
O2 C1 C2 O3 171.0(9) . . . . ?
C2 O3 C3 C4 0.3(3) . . . . ?
O3 C3 C4 C5 0.0(3) . . . . ?
O3 C2 C5 C4 0.5(2) . . . . ?
C1 C2 C5 C4 -176.90(18) . . . . ?
C3 C4 C5 C2 -0.3(2) . . . . ?
Zn1 O5 C6 O4 -24(3) 2_566 . . . ?
Zn1 O5 C6 C7 154.2(13) 2_566 . . . ?
Zn1 O4' C6 O5' 32.5(19) . . . . ?
Zn1 O4' C6 C7 -157.6(5) . . . . ?
Zn1 O5' C6 O4' -14(3) 2_566 . . . ?
Zn1 O5' C6 C7 176.3(13) 2_566 . . . ?
Zn1 O4 C6 O5 -10.1(19) . . . . ?
Zn1 O4 C6 C7 171.7(4) . . . . ?
C8 O6 C7 C10 0.9(3) . . . . ?
C8 O6 C7 C6 -176.79(17) . . . . ?
O5 C6 C7 C10 179.5(16) . . . . ?
O4' C6 C7 C10 32.7(8) . . . . ?
O5' C6 C7 C10 -156.5(14) . . . . ?
O4 C6 C7 C10 -2.2(6) . . . . ?
O5 C6 C7 O6 -3.5(16) . . . . ?
O4' C6 C7 O6 -150.4(7) . . . . ?
O5' C6 C7 O6 20.4(14) . . . . ?
O4 C6 C7 O6 174.8(5) . . . . ?
C7 O6 C8 C9 0.4(3) . . . . ?
O6 C8 C9 C10 -1.4(3) . . . . ?
O6 C7 C10 C9 -1.7(3) . . . . ?
C6 C7 C10 C9 175.4(2) . . . . ?
C8 C9 C10 C7 1.9(4) . . . . ?
C15 N1 C11 C12 0.0(2) . . . . ?
Zn1 N1 C11 C12 175.72(12) . . . . ?
N1 C11 C12 N2 -176.96(16) . . . . ?
N1 C11 C12 C13 -0.3(3) . . . . ?
N2 C12 C13 C14 177.17(17) . . . . ?
C11 C12 C13 C14 0.6(3) . . . . ?
C12 C13 C14 C15 -0.5(3) . . . . ?
C11 N1 C15 C14 0.2(3) . . . . ?
Zn1 N1 C15 C14 -175.73(14) . . . . ?
C13 C14 C15 N1 0.1(3) . . . . ?

_refine_diff_density_max         0.536
_refine_diff_density_min         -0.305
_refine_diff_density_rms         0.065

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

data_1
_database_code_depnum_ccdc_archive 'CCDC 2112367'
loop_
_audit_author_name
_audit_author_address
'Petr Primakov'
;A N Nesmeyanov Institute of Organoelement Compounds of Russian Academy of Sciences
Russia
;
_audit_update_record             
;
2022-01-14 deposited with the CCDC.	2022-02-04 downloaded from the CCDC.
;
_audit_creation_date             2022-01-14
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H12 O12 Zn2'
_chemical_formula_sum            'C20 H12 O12 Zn2'
_chemical_formula_weight         575.04
_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'
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/n 1'
_space_group_name_Hall           '-P 2yn'
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                   13.5158(7)
_cell_length_b                   12.8924(6)
_cell_length_c                   13.8937(7)
_cell_angle_alpha                90
_cell_angle_beta                 91.1060(10)
_cell_angle_gamma                90
_cell_volume                     2420.5(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5799
_cell_measurement_temperature    120
_cell_measurement_theta_max      28.81
_cell_measurement_theta_min      2.18
_shelx_estimated_absorpt_T_max   0.980
_shelx_estimated_absorpt_T_min   0.960
_exptl_absorpt_coefficient_mu    2.040
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.5829
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0655 before and 0.0386 after correction.
The Ratio of minimum to maximum transmission is 0.7813.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.578
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             1152
_exptl_crystal_size_max          0.02
_exptl_crystal_size_mid          0.01
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0275
_diffrn_reflns_av_unetI/netI     0.0287
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            15047
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.996
_diffrn_reflns_theta_min         2.082
_diffrn_ambient_temperature      120.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3891
_reflns_number_total             4747
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.601
_refine_diff_density_min         -0.402
_refine_diff_density_rms         0.073
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     372
_refine_ls_number_reflns         4747
_refine_ls_number_restraints     54
_refine_ls_R_factor_all          0.0438
_refine_ls_R_factor_gt           0.0326
_refine_ls_restrained_S_all      1.054
_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)+(0.0454P)²+2.6537P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0833
_refine_ls_wR_factor_ref         0.0909
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Restrained distances
 C34-C9
 2.2 with sigma of 0.02
 C12-C15A
 2.2 with sigma of 0.03
 C18-C20 \\sim C18A-C20A
 with sigma of 0.04
 O12-C20 \\sim O12A-C20A
 with sigma of 0.02
 O12-C17 \\sim O12A-C17
 with sigma of 0.02
 C17-C18 \\sim C17-C18A
 with sigma of 0.02
 C17-C20 \\sim C17-C20A
 with sigma of 0.04
 C18-C19 \\sim C18A-C19A
 with sigma of 0.02
 C17-C19 \\sim C17-C19A
 with sigma of 0.04
 C19-C20 \\sim C19A-C20A
 with sigma of 0.02
 O12-C19 \\sim O12A-C19A
 with sigma of 0.04
 C12-C13 \\sim C12-C13A
 with sigma of 0.02
 O9-C14 \\sim O9-C14A
 with sigma of 0.04
 C13-C14 \\sim C13A-C14A
 with sigma of 0.02
 C13-C15 \\sim C13A-C15A
 with sigma of 0.04
 C12-C14 \\sim C12-C14A
 with sigma of 0.04
 C15-C14 \\sim C15A-C14A
 with sigma of 0.02
 O9-C15 \\sim O9-C15A
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C9) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01
Uanis(C19A) \\sim Ueq, Uanis(C18A) \\sim Ueq, Uanis(O12A) \\sim Ueq,
Uanis(C20A) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C18A) \\sim Ueq, Uanis(C20) \\sim Ueq: with sigma of 0.001 and sigma for
terminal atoms of 0.002
Uanis(C20A) \\sim Ueq: with sigma of 0.001 and sigma for terminal atoms of 0.002
Uanis(O6) = Uanis(C34)
Uanis(C14A) = Uanis(C14)
Uanis(C15A) = Uanis(C15)
4. Others
 Sof(C18A)=Sof(H18A)=Sof(C19A)=Sof(H19A)=Sof(C20A)=Sof(H20A)=Sof(O12A)=1-FVAR(1)
 Sof(O12)=Sof(C18)=Sof(H18)=Sof(C19)=Sof(H19)=Sof(C20)=Sof(H20)=FVAR(1)
 Sof(C15A)=Sof(H15A)=Sof(C13A)=Sof(H13A)=Sof(C14A)=Sof(H14A)=1-FVAR(2)
 Sof(C13)=Sof(H13)=Sof(C15)=Sof(H15)=Sof(C14)=Sof(H14)=FVAR(2)
 Fixed Sof: O6(0.5) C8(0.5) H8(0.5) H10(0.5) H10A(0.5) O13(0.5) C34(0.5)
 H34(0.5)
5.a Aromatic/amide H refined with riding coordinates:
 C8(H8), C3(H3), C18(H18), C10(H10), C10(H10A), C5(H5), C9(H9), C4(H4),
 C19(H19), C13(H13), C20(H20), C15(H15), C14(H14), C34(H34), C18A(H18A),
 C19A(H19A), C20A(H20A), C15A(H15A), C13A(H13A), C14A(H14A)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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 0.37946(2) 0.27968(2) 0.28904(2) 0.02355(10) Uani 1 1 d . . . . .
Zn2 Zn 0.21475(3) 0.45042(3) 0.20929(2) 0.03087(11) Uani 1 1 d . . . . .
O11 O 0.01561(13) 0.68574(14) 0.16389(14) 0.0229(4) Uani 1 1 d . . . . .
O7 O 0.46025(15) 0.40273(16) 0.26200(15) 0.0316(5) Uani 1 1 d . . . . .
O10 O 0.13585(14) 0.57198(15) 0.18194(15) 0.0268(4) Uani 1 1 d . . . . .
O4 O 0.32609(16) 0.23175(17) 0.16570(15) 0.0332(5) Uani 1 1 d . . . . .
O1 O 0.28750(16) 0.30116(17) 0.39236(15) 0.0349(5) Uani 1 1 d . . . . .
O2 O 0.16252(15) 0.39454(19) 0.32796(16) 0.0384(5) Uani 1 1 d . . . . .
O5 O 0.22015(19) 0.35023(19) 0.10679(17) 0.0462(6) Uani 1 1 d . . . . .
O8 O 0.34056(16) 0.52072(19) 0.23505(19) 0.0461(6) Uani 1 1 d . . . . .
O9 O 0.60173(18) 0.5463(2) 0.22727(19) 0.0475(6) Uani 1 1 d D . . . .
O12 O 0.0149(6) 0.4148(5) 0.1352(7) 0.0431(18) Uani 0.683(16) 1 d D . P A 1
O6 O 0.1878(11) 0.2310(10) -0.0512(18) 0.029(2) Uani 0.5 1 d . . P B 1
O3 O 0.06278(19) 0.3836(3) 0.4999(2) 0.0611(8) Uani 1 1 d . . . . .
C17 C -0.0219(2) 0.5131(2) 0.1273(2) 0.0230(6) Uani 1 1 d D . . . .
C16 C 0.04744(19) 0.5935(2) 0.15960(18) 0.0206(5) Uani 1 1 d . . . . .
C6 C 0.2662(2) 0.2651(2) 0.1036(2) 0.0269(6) Uani 1 1 d . . . . .
C8 C 0.2892(18) 0.102(2) -0.005(2) 0.035(4) Uani 0.5 1 d . . P B 1
H8 H 0.3385 0.0654 0.0303 0.042 Uiso 0.5 1 calc R U P B 1
C7 C 0.2470(2) 0.1991(2) 0.0196(2) 0.0276(6) Uani 1 1 d . . . . .
C3 C 0.1862(2) 0.2966(3) 0.5683(2) 0.0375(8) Uani 1 1 d . . . . .
H3 H 0.2473 0.2614 0.5779 0.045 Uiso 1 1 calc R U . . .
C1 C 0.2043(2) 0.3454(2) 0.3952(2) 0.0267(6) Uani 1 1 d . . . . .
C2 C 0.1520(2) 0.3391(2) 0.4865(2) 0.0325(7) Uani 1 1 d . . . . .
C18 C -0.1113(3) 0.5200(4) 0.0823(5) 0.0201(12) Uani 0.683(16) 1 d D . P A 1
H18 H -0.1494 0.5804 0.0688 0.024 Uiso 0.683(16) 1 calc R U P A 1
C11 C 0.4298(2) 0.4923(2) 0.2428(2) 0.0308(7) Uani 1 1 d . . . . .
C12 C 0.5035(2) 0.5738(3) 0.2266(2) 0.0377(7) Uani 1 1 d D . . . .
C10 C 0.1822(3) 0.1434(3) -0.1155(3) 0.0520(10) Uani 1 1 d . . . . .
H10 H 0.1387 0.1370 -0.1697 0.062 Uiso 0.5 1 calc R U P B 1
H10A H 0.1483 0.1419 -0.1761 0.062 Uiso 0.5 1 calc R U P B 2
C5 C 0.0384(3) 0.3635(4) 0.5947(3) 0.0667(13) Uani 1 1 d . . . . .
H5 H -0.0221 0.3821 0.6238 0.080 Uiso 1 1 calc R U . . .
C9 C 0.2480(4) 0.0735(3) -0.0866(3) 0.0575(11) Uani 1 1 d D U . . .
H9 H 0.2629 0.0114 -0.1201 0.069 Uiso 1 1 calc R U . B 1
C4 C 0.1124(3) 0.3146(4) 0.6379(3) 0.0641(12) Uani 1 1 d . . . . .
H4 H 0.1159 0.2950 0.7038 0.077 Uiso 1 1 calc R U . . .
C19 C -0.1350(6) 0.4121(7) 0.0593(5) 0.0339(17) Uani 0.683(16) 1 d D . P A 1
H19 H -0.1935 0.3877 0.0278 0.041 Uiso 0.683(16) 1 calc R U P A 1
C13 C 0.4983(10) 0.6786(6) 0.2143(11) 0.045(3) Uani 0.71(4) 1 d D . P C 1
H13 H 0.4400 0.7199 0.2129 0.054 Uiso 0.71(4) 1 calc R U P C 1
C20 C -0.0588(6) 0.3539(5) 0.0911(4) 0.0376(16) Uani 0.683(16) 1 d D U P A 1
H20 H -0.0553 0.2807 0.0846 0.045 Uiso 0.683(16) 1 calc R U P A 1
C15 C 0.6571(9) 0.6338(7) 0.2146(12) 0.057(3) Uani 0.71(4) 1 d D . P C 1
H15 H 0.7274 0.6357 0.2137 0.068 Uiso 0.71(4) 1 calc R U P C 1
C14 C 0.5990(12) 0.7147(6) 0.2037(11) 0.063(3) Uani 0.71(4) 1 d D . P C 1
H14 H 0.6192 0.7839 0.1913 0.075 Uiso 0.71(4) 1 calc R U P C 1
O13 O 0.2966(15) 0.1154(16) 0.0041(17) 0.055(5) Uani 0.5 1 d . . P B 2
C34 C 0.1699(18) 0.2151(16) -0.050(3) 0.029(2) Uani 0.5 1 d D . P B 2
H34 H 0.1199 0.2669 -0.0491 0.035 Uiso 0.5 1 calc R U P B 2
C18A C -0.1187(7) 0.5357(8) 0.1181(11) 0.019(3) Uani 0.317(16) 1 d D U P A 2
H18A H -0.1498 0.5985 0.1365 0.022 Uiso 0.317(16) 1 calc R U P A 2
C19A C -0.1653(11) 0.4490(14) 0.0759(12) 0.042(4) Uani 0.317(16) 1 d D U P A 2
H19A H -0.2317 0.4463 0.0523 0.050 Uiso 0.317(16) 1 calc R U P A 2
C20A C -0.1002(13) 0.3710(10) 0.0748(9) 0.029(4) Uani 0.317(16) 1 d D U P A 2
H20A H -0.1130 0.3023 0.0530 0.035 Uiso 0.317(16) 1 calc R U P A 2
O12A O -0.0072(11) 0.4096(10) 0.1125(14) 0.035(4) Uani 0.317(16) 1 d D U P A 2
C15A C 0.6402(17) 0.6391(16) 0.191(3) 0.057(3) Uani 0.29(4) 1 d D . P C 2
H15A H 0.7082 0.6476 0.1767 0.068 Uiso 0.29(4) 1 calc R U P C 2
C13A C 0.477(2) 0.6699(16) 0.193(3) 0.061(9) Uani 0.29(4) 1 d D . P C 2
H13A H 0.4129 0.6993 0.1824 0.073 Uiso 0.29(4) 1 calc R U P C 2
C14A C 0.574(2) 0.7136(15) 0.178(2) 0.063(3) Uani 0.29(4) 1 d D . P C 2
H14A H 0.5885 0.7836 0.1618 0.075 Uiso 0.29(4) 1 calc R U P C 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Zn1 O11 1.9672(18) 2_545 ?
Zn1 O7 1.966(2) . ?
Zn1 O4 1.947(2) . ?
Zn1 O1 1.937(2) . ?
Zn2 O10 1.9292(19) . ?
Zn2 O2 1.944(2) . ?
Zn2 O5 1.925(2) . ?
Zn2 O8 1.954(2) . ?
O11 Zn1 1.9672(18) 2 ?
O11 C16 1.266(3) . ?
O7 C11 1.253(4) . ?
O10 C16 1.260(3) . ?
O4 C6 1.248(3) . ?
O1 C1 1.261(4) . ?
O2 C1 1.255(4) . ?
O5 C6 1.263(4) . ?
O8 C11 1.263(4) . ?
O9 C12 1.374(4) . ?
O9 C15 1.367(7) . ?
O9 C15A 1.403(15) . ?
O12 C17 1.364(7) . ?
O12 C20 1.399(8) . ?
O6 C7 1.32(2) . ?
O6 C10 1.441(17) . ?
O3 C2 1.351(4) . ?
O3 C5 1.389(4) . ?
C17 C16 1.463(4) . ?
C17 C18 1.353(5) . ?
C17 C18A 1.344(10) . ?
C17 O12A 1.364(12) . ?
C6 C7 1.463(4) . ?
C8 H8 0.9500 . ?
C8 C7 1.42(3) . ?
C8 C9 1.30(3) . ?
C7 O13 1.290(19) . ?
C7 C34 1.42(3) . ?
C3 H3 0.9500 . ?
C3 C2 1.335(5) . ?
C3 C4 1.422(5) . ?
C1 C2 1.466(4) . ?
C18 H18 0.9500 . ?
C18 C19 1.461(7) . ?
C11 C12 1.468(4) . ?
C12 C13 1.364(8) . ?
C12 C13A 1.370(15) . ?
C10 H10 0.9500 . ?
C10 H10A 0.9500 . ?
C10 C9 1.323(6) . ?
C10 C34 1.31(3) . ?
C5 H5 0.9500 . ?
C5 C4 1.317(6) . ?
C9 H9 0.9500 . ?
C9 O13 1.51(2) . ?
C4 H4 0.9500 . ?
C19 H19 0.9500 . ?
C19 C20 1.342(8) . ?
C13 H13 0.9500 . ?
C13 C14 1.449(9) . ?
C20 H20 0.9500 . ?
C15 H15 0.9500 . ?
C15 C14 1.313(9) . ?
C14 H14 0.9500 . ?
C34 H34 0.9500 . ?
C18A H18A 0.9500 . ?
C18A C19A 1.405(13) . ?
C19A H19A 0.9500 . ?
C19A C20A 1.337(14) . ?
C20A H20A 0.9500 . ?
C20A O12A 1.442(14) . ?
C15A H15A 0.9500 . ?
C15A C14A 1.318(16) . ?
C13A H13A 0.9500 . ?
C13A C14A 1.456(17) . ?
C14A H14A 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O7 Zn1 O11 99.25(8) . 2_545 ?
O4 Zn1 O11 110.47(8) . 2_545 ?
O4 Zn1 O7 106.60(9) . . ?
O1 Zn1 O11 108.09(8) . 2_545 ?
O1 Zn1 O7 113.14(9) . . ?
O1 Zn1 O4 117.75(10) . . ?
O10 Zn2 O2 105.05(9) . . ?
O10 Zn2 O8 97.76(9) . . ?
O2 Zn2 O8 110.21(10) . . ?
O5 Zn2 O10 115.35(9) . . ?
O5 Zn2 O2 113.47(11) . . ?
O5 Zn2 O8 113.67(11) . . ?
C16 O11 Zn1 110.51(16) . 2 ?
C11 O7 Zn1 127.06(19) . . ?
C16 O10 Zn2 138.21(18) . . ?
C6 O4 Zn1 136.3(2) . . ?
C1 O1 Zn1 132.3(2) . . ?
C1 O2 Zn2 130.8(2) . . ?
C6 O5 Zn2 129.4(2) . . ?
C11 O8 Zn2 135.0(2) . . ?
C12 O9 C15A 98.2(11) . . ?
C15 O9 C12 108.5(6) . . ?
C17 O12 C20 103.3(5) . . ?
C7 O6 C10 104.0(9) . . ?
C2 O3 C5 106.2(3) . . ?
O12 C17 C16 113.8(4) . . ?
C18 C17 O12 114.8(4) . . ?
C18 C17 C16 131.0(3) . . ?
C18A C17 C16 119.5(6) . . ?
C18A C17 O12A 110.0(7) . . ?
O12A C17 C16 130.1(7) . . ?
O11 C16 C17 117.7(2) . . ?
O10 C16 O11 121.1(2) . . ?
O10 C16 C17 121.2(2) . . ?
O4 C6 O5 126.0(3) . . ?
O4 C6 C7 117.0(3) . . ?
O5 C6 C7 117.0(3) . . ?
C7 C8 H8 126.4 . . ?
C9 C8 H8 126.4 . . ?
C9 C8 C7 107.2(14) . . ?
O6 C7 C6 120.5(7) . . ?
O6 C7 C8 109.4(14) . . ?
C8 C7 C6 129.9(12) . . ?
O13 C7 C6 122.3(10) . . ?
O13 C7 C34 112.6(13) . . ?
C34 C7 C6 125.0(9) . . ?
C2 C3 H3 127.0 . . ?
C2 C3 C4 106.0(3) . . ?
C4 C3 H3 127.0 . . ?
O1 C1 C2 116.6(3) . . ?
O2 C1 O1 126.4(3) . . ?
O2 C1 C2 117.0(3) . . ?
O3 C2 C1 122.8(3) . . ?
C3 C2 O3 110.7(3) . . ?
C3 C2 C1 126.4(3) . . ?
C17 C18 H18 128.4 . . ?
C17 C18 C19 103.2(4) . . ?
C19 C18 H18 128.4 . . ?
O7 C11 O8 126.5(3) . . ?
O7 C11 C12 118.1(3) . . ?
O8 C11 C12 115.4(3) . . ?
O9 C12 C11 118.2(3) . . ?
C13 C12 O9 107.7(6) . . ?
C13 C12 C11 134.0(6) . . ?
C13A C12 O9 119.0(12) . . ?
C13A C12 C11 121.6(12) . . ?
O6 C10 H10 125.7 . . ?
C9 C10 O6 108.5(8) . . ?
C9 C10 H10 125.7 . . ?
C9 C10 H10A 124.4 . . ?
C34 C10 H10A 124.4 . . ?
C34 C10 C9 111.3(15) . . ?
O3 C5 H5 125.4 . . ?
C4 C5 O3 109.3(3) . . ?
C4 C5 H5 125.4 . . ?
C8 C9 C10 110.1(10) . . ?
C8 C9 H9 125.0 . . ?
C10 C9 H9 125.0 . . ?
C10 C9 O13 106.8(7) . . ?
C3 C4 H4 126.1 . . ?
C5 C4 C3 107.7(3) . . ?
C5 C4 H4 126.1 . . ?
C18 C19 H19 126.4 . . ?
C20 C19 C18 107.2(4) . . ?
C20 C19 H19 126.4 . . ?
C12 C13 H13 126.7 . . ?
C12 C13 C14 106.5(6) . . ?
C14 C13 H13 126.7 . . ?
O12 C20 H20 124.3 . . ?
C19 C20 O12 111.5(5) . . ?
C19 C20 H20 124.3 . . ?
O9 C15 H15 125.0 . . ?
C14 C15 O9 110.0(6) . . ?
C14 C15 H15 125.0 . . ?
C13 C14 H14 126.4 . . ?
C15 C14 C13 107.2(6) . . ?
C15 C14 H14 126.4 . . ?
C7 O13 C9 102.7(12) . . ?
C7 C34 H34 127.2 . . ?
C10 C34 C7 105.6(14) . . ?
C10 C34 H34 127.2 . . ?
C17 C18A H18A 126.4 . . ?
C17 C18A C19A 107.2(9) . . ?
C19A C18A H18A 126.4 . . ?
C18A C19A H19A 125.9 . . ?
C20A C19A C18A 108.3(10) . . ?
C20A C19A H19A 125.9 . . ?
C19A C20A H20A 126.1 . . ?
C19A C20A O12A 107.8(10) . . ?
O12A C20A H20A 126.1 . . ?
C17 O12A C20A 105.3(9) . . ?
O9 C15A H15A 122.7 . . ?
C14A C15A O9 114.7(14) . . ?
C14A C15A H15A 122.7 . . ?
C12 C13A H13A 130.3 . . ?
C12 C13A C14A 99.4(14) . . ?
C14A C13A H13A 130.3 . . ?
C15A C14A C13A 108.1(14) . . ?
C15A C14A H14A 126.0 . . ?
C13A C14A H14A 126.0 . . ?

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
Zn1 O11 C16 O10 -1.3(3) 2 . . . ?
Zn1 O11 C16 C17 179.02(18) 2 . . . ?
Zn1 O7 C11 O8 -1.5(5) . . . . ?
Zn1 O7 C11 C12 178.9(2) . . . . ?
Zn1 O4 C6 O5 0.4(5) . . . . ?
Zn1 O4 C6 C7 -179.1(2) . . . . ?
Zn1 O1 C1 O2 -5.2(5) . . . . ?
Zn1 O1 C1 C2 175.3(2) . . . . ?
Zn2 O10 C16 O11 166.69(19) . . . . ?
Zn2 O10 C16 C17 -13.6(4) . . . . ?
Zn2 O2 C1 O1 -16.2(5) . . . . ?
Zn2 O2 C1 C2 163.3(2) . . . . ?
Zn2 O5 C6 O4 -6.4(5) . . . . ?
Zn2 O5 C6 C7 173.0(2) . . . . ?
Zn2 O8 C11 O7 -21.8(5) . . . . ?
Zn2 O8 C11 C12 157.8(3) . . . . ?
O7 C11 C12 O9 4.1(5) . . . . ?
O7 C11 C12 C13 -172.2(10) . . . . ?
O7 C11 C12 C13A 171(2) . . . . ?
O4 C6 C7 O6 -177.1(9) . . . . ?
O4 C6 C7 C8 -2.8(16) . . . . ?
O4 C6 C7 O13 -7.3(13) . . . . ?
O4 C6 C7 C34 168.9(15) . . . . ?
O1 C1 C2 O3 179.5(3) . . . . ?
O1 C1 C2 C3 4.2(5) . . . . ?
O2 C1 C2 O3 -0.1(5) . . . . ?
O2 C1 C2 C3 -175.4(3) . . . . ?
O5 C6 C7 O6 3.4(9) . . . . ?
O5 C6 C7 C8 177.7(16) . . . . ?
O5 C6 C7 O13 173.2(13) . . . . ?
O5 C6 C7 C34 -10.6(15) . . . . ?
O8 C11 C12 O9 -175.5(3) . . . . ?
O8 C11 C12 C13 8.2(10) . . . . ?
O8 C11 C12 C13A -8(2) . . . . ?
O9 C12 C13 C14 2.1(9) . . . . ?
O9 C12 C13A C14A -6(3) . . . . ?
O9 C15 C14 C13 2.6(11) . . . . ?
O9 C15A C14A C13A -8(4) . . . . ?
O12 C17 C16 O11 -173.0(5) . . . . ?
O12 C17 C16 O10 7.3(6) . . . . ?
O12 C17 C18 C19 0.7(7) . . . . ?
O6 C10 C9 C8 5.7(16) . . . . ?
O3 C5 C4 C3 -3.2(6) . . . . ?
C17 O12 C20 C19 -0.2(9) . . . . ?
C17 C18 C19 C20 -0.8(6) . . . . ?
C17 C18A C19A C20A 9.7(15) . . . . ?
C16 C17 C18 C19 172.8(4) . . . . ?
C16 C17 C18A C19A 173.3(8) . . . . ?
C16 C17 O12A C20A -176.2(6) . . . . ?
C6 C7 O13 C9 177.9(6) . . . . ?
C6 C7 C34 C10 176.2(9) . . . . ?
C7 O6 C10 C9 -8.9(12) . . . . ?
C7 C8 C9 C10 0(2) . . . . ?
C2 O3 C5 C4 3.6(5) . . . . ?
C2 C3 C4 C5 1.6(5) . . . . ?
C18 C17 C16 O11 14.9(6) . . . . ?
C18 C17 C16 O10 -164.8(5) . . . . ?
C18 C19 C20 O12 0.6(8) . . . . ?
C11 C12 C13 C14 178.6(7) . . . . ?
C11 C12 C13A C14A -172.8(13) . . . . ?
C12 O9 C15 C14 -1.4(9) . . . . ?
C12 O9 C15A C14A 5(3) . . . . ?
C12 C13 C14 C15 -2.9(11) . . . . ?
C12 C13A C14A C15A 8(3) . . . . ?
C10 O6 C7 C6 -176.1(5) . . . . ?
C10 O6 C7 C8 8.6(17) . . . . ?
C10 C9 O13 C7 5.1(16) . . . . ?
C5 O3 C2 C3 -2.6(4) . . . . ?
C5 O3 C2 C1 -178.5(3) . . . . ?
C9 C8 C7 O6 -6(2) . . . . ?
C9 C8 C7 C6 179.6(8) . . . . ?
C9 C10 C34 C7 11(2) . . . . ?
C4 C3 C2 O3 0.7(4) . . . . ?
C4 C3 C2 C1 176.4(3) . . . . ?
C20 O12 C17 C16 -173.8(5) . . . . ?
C20 O12 C17 C18 -0.3(9) . . . . ?
C15 O9 C12 C11 -177.7(8) . . . . ?
C15 O9 C12 C13 -0.6(8) . . . . ?
O13 C7 C34 C10 -7(3) . . . . ?
C34 C7 O13 C9 1(2) . . . . ?
C34 C10 C9 O13 -10.2(17) . . . . ?
C18A C17 C16 O11 -10.3(8) . . . . ?
C18A C17 C16 O10 170.0(7) . . . . ?
C18A C17 O12A C20A 10.7(15) . . . . ?
C18A C19A C20A O12A -3.1(17) . . . . ?
C19A C20A O12A C17 -4.4(17) . . . . ?
O12A C17 C16 O11 177.2(11) . . . . ?
O12A C17 C16 O10 -2.5(12) . . . . ?
O12A C17 C18A C19A -12.7(14) . . . . ?
C15A O9 C12 C11 168.8(16) . . . . ?
C15A O9 C12 C13A 1(2) . . . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.000 0.000 0.000 72.1 20.1 ?
2 0.000 0.000 0.500 102.3 16.3 ?
3 0.500 0.500 0.000 102.3 16.3 ?
4 0.500 0.500 0.500 72.1 20.1 ?

_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_3
_database_code_depnum_ccdc_archive 'CCDC 2112369'
loop_
_audit_author_name
_audit_author_address
'Petr Primakov'
;A N Nesmeyanov Institute of Organoelement Compounds of Russian Academy of Sciences
Russia
;
_audit_update_record             
;
2021-10-11 deposited with the CCDC.	2022-02-04 downloaded from the CCDC.
;
_audit_creation_date             2021-08-05
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_chemical_formula_moiety         'C24 H18 N2 O6 Zn'
_chemical_formula_sum            'C24 H18 N2 O6 Zn'
_chemical_formula_weight         495.816
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Zn 0.31207 1.46666 14.07430 7.03180 5.16520 2.41000 3.26550 0.23330 10.31630
58.70970 1.30410003662
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,-y,-z

_symmetry_Int_Tables_number      2
_cell_length_a                   9.622(3)
_cell_length_b                   10.595(3)
_cell_length_c                   11.815(3)
_cell_angle_alpha                78.455(5)
_cell_angle_beta                 76.399(5)
_cell_angle_gamma                65.951(5)
_cell_volume                     1061.7(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4528
_cell_measurement_temperature    120
_cell_measurement_theta_max      30.33
_cell_measurement_theta_min      2.35
_exptl_absorpt_coefficient_mu    1.202
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6369
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0668 before and 0.0544 after correction.
The Ratio of minimum to maximum transmission is 0.8536.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.551
_exptl_crystal_density_meas      .
_exptl_crystal_description       prism
_exptl_crystal_F_000             508.928
_exptl_crystal_size_max          0.03
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_diffrn_reflns_av_R_equivalents  0.0616
_diffrn_reflns_av_unetI/netI     0.0769
_diffrn_reflns_Laue_measured_fraction_full 0.9922
_diffrn_reflns_Laue_measured_fraction_max 0.9928
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            18637
_diffrn_reflns_point_group_measured_fraction_full 0.9922
_diffrn_reflns_point_group_measured_fraction_max 0.9928
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.12
_diffrn_ambient_temperature      120
_diffrn_measured_fraction_theta_full 0.9922
_diffrn_measured_fraction_theta_max 0.9928
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              11
_reflns_limit_h_min              -11
_reflns_limit_k_max              13
_reflns_limit_k_min              -12
_reflns_limit_l_max              14
_reflns_limit_l_min              0
_reflns_number_gt                3371
_reflns_number_total             4140
_reflns_threshold_expression     I>=2u(I)
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.3 (Bourhis et al., 2015)'
_refine_diff_density_max         1.1207
_refine_diff_density_min         -0.4614
_refine_diff_density_rms         0.1037
_refine_ls_d_res_high            0.8107
_refine_ls_d_res_low             9.6086
_refine_ls_goodness_of_fit_ref   1.0036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    32
_refine_ls_number_parameters     300
_refine_ls_number_reflns         4140
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0511
_refine_ls_R_factor_gt           0.0365
_refine_ls_restrained_S_all      1.0036
_refine_ls_shift/su_max          0.0005
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0491P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0823
_refine_ls_wR_factor_ref         0.0881
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C8(H8), C16(H16), C20(H20), C5(H5), C17(H17), C13(H13), C9(H9), C14(H14),
 C19(H19), C10(H10), C4(H4), C3(H3)
2.b Idealised Me refined as rotating group:
 C22(H22a,H22b,H22c), C11(H11a,H11b,H11c)
;
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_refinement_flags_posn
Zn1 Zn 0.69202(3) 0.77511(3) 0.73565(2) 0.01940(11) Uani 1.000000 .
O3 O 0.6271(2) 0.33146(18) 0.76209(15) 0.0238(4) Uani 1.000000 .
O4 O 0.8089(2) 0.72488(18) 0.86294(15) 0.0234(4) Uani 1.000000 .
O6 O 1.0235(2) 0.86263(19) 0.97223(15) 0.0261(4) Uani 1.000000 .
O5 O 0.8315(2) 0.93119(19) 0.81357(16) 0.0277(4) Uani 1.000000 .
O1 O 0.5486(2) 0.6778(2) 0.80088(18) 0.0347(5) Uani 1.000000 .
N2 N 0.5550(2) 0.9748(2) 0.67565(17) 0.0187(4) Uani 1.000000 .
N1 N 0.8418(2) 0.8020(2) 0.58564(17) 0.0195(4) Uani 1.000000 .
O2 O 0.7213(2) 0.5470(2) 0.66987(19) 0.0392(5) Uani 1.000000 .
C24 C 0.7829(3) 0.9324(3) 0.5285(2) 0.0194(5) Uani 1.000000 .
C6 C 0.8595(3) 0.8163(3) 0.8724(2) 0.0189(5) Uani 1.000000 .
C23 C 0.6321(3) 1.0233(3) 0.5758(2) 0.0196(5) Uani 1.000000 .
C2 C 0.5487(3) 0.4583(3) 0.8031(2) 0.0215(5) Uani 1.000000 .
C21 C 0.4136(3) 1.0550(3) 0.7205(2) 0.0218(5) Uani 1.000000 .
C7 C 0.9556(3) 0.7742(3) 0.9642(2) 0.0196(5) Uani 1.000000 .
C15 C 0.8659(3) 0.9785(3) 0.4252(2) 0.0239(6) Uani 1.000000 .
C1 C 0.6116(3) 0.5666(3) 0.7526(3) 0.0275(6) Uani 1.000000 .
C8 C 0.9863(3) 0.6674(3) 1.0510(2) 0.0224(5) Uani 1.000000 .
H8 H 0.9531(3) 0.5918(3) 1.0647(2) 0.0268(7) Uiso 1.000000 R
C16 C 0.7969(3) 1.1176(3) 0.3709(2) 0.0290(6) Uani 1.000000 .
H16 H 0.8527(3) 1.1498(3) 0.3017(2) 0.0348(8) Uiso 1.000000 R
C20 C 0.3404(3) 1.1903(3) 0.6650(2) 0.0265(6) Uani 1.000000 .
H20 H 0.2378(3) 1.2460(3) 0.6966(2) 0.0318(7) Uiso 1.000000 R
C18 C 0.5672(3) 1.1585(3) 0.5186(2) 0.0236(6) Uani 1.000000 .
C5 C 0.5568(3) 0.2462(3) 0.8282(2) 0.0270(6) Uani 1.000000 .
H5 H 0.5877(3) 0.1507(3) 0.8198(2) 0.0325(7) Uiso 1.000000 R
C12 C 0.9817(3) 0.7153(3) 0.5450(2) 0.0239(6) Uani 1.000000 .
C22 C 0.3347(3) 1.0011(3) 0.8331(2) 0.0282(6) Uani 1.000000 .
H22a H 0.3640(18) 0.9007(5) 0.8353(8) 0.0423(9) Uiso 1.000000 GR
H22b H 0.3660(17) 1.0193(18) 0.8994(2) 0.0423(9) Uiso 1.000000 GR
H22c H 0.2225(3) 1.0481(15) 0.8382(8) 0.0423(9) Uiso 1.000000 GR
C17 C 0.6566(3) 1.2033(3) 0.4149(2) 0.0286(6) Uani 1.000000 .
H17 H 0.6150(3) 1.2954(3) 0.3772(2) 0.0344(8) Uiso 1.000000 R
C13 C 1.0691(3) 0.7536(3) 0.4409(2) 0.0285(6) Uani 1.000000 .
H13 H 1.1680(3) 0.6891(3) 0.4116(2) 0.0342(7) Uiso 1.000000 R
C9 C 1.0770(3) 0.6892(3) 1.1175(2) 0.0267(6) Uani 1.000000 .
H9 H 1.1163(3) 0.6317(3) 1.1846(2) 0.0321(7) Uiso 1.000000 R
C14 C 1.0117(3) 0.8837(3) 0.3820(2) 0.0291(6) Uani 1.000000 .
H14 H 1.0707(3) 0.9097(3) 0.3117(2) 0.0350(8) Uiso 1.000000 R
C19 C 0.4166(3) 1.2406(3) 0.5665(2) 0.0285(6) Uani 1.000000 .
H19 H 0.3675(3) 1.3320(3) 0.5300(2) 0.0342(7) Uiso 1.000000 R
C10 C 1.0969(3) 0.8081(3) 1.0666(2) 0.0298(6) Uani 1.000000 .
H10 H 1.1541(3) 0.8482(3) 1.0930(2) 0.0358(8) Uiso 1.000000 R
C11 C 1.0479(3) 0.5759(3) 0.6136(3) 0.0311(6) Uani 1.000000 .
H11a H 1.085(2) 0.5862(4) 0.6804(10) 0.0466(10) Uiso 1.000000 GR
H11b H 0.9680(7) 0.5366(9) 0.6422(14) 0.0466(10) Uiso 1.000000 GR
H11c H 1.1342(14) 0.5135(7) 0.5631(5) 0.0466(10) Uiso 1.000000 GR
C4 C 0.4388(3) 0.3151(3) 0.9062(2) 0.0314(7) Uani 1.000000 .
H4 H 0.3715(3) 0.2786(3) 0.9618(2) 0.0377(8) Uiso 1.000000 R
C3 C 0.4329(3) 0.4522(3) 0.8905(2) 0.0295(6) Uani 1.000000 .
H3 H 0.3610(3) 0.5262(3) 0.9334(2) 0.0354(8) Uiso 1.000000 R


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 1.9485(18) . ?
Zn1 O1 1.976(2) . ?
Zn1 N2 2.070(2) . ?
Zn1 N1 2.057(2) . ?
Zn1 C1 2.581(3) . ?
O3 C2 1.368(3) . ?
O3 C5 1.360(3) . ?
O4 C6 1.281(3) . ?
O6 C7 1.370(3) . ?
O6 C10 1.362(3) . ?
O5 C6 1.233(3) . ?
O1 C1 1.267(3) . ?
N2 C23 1.365(3) . ?
N2 C21 1.324(3) . ?
N1 C24 1.361(3) . ?
N1 C12 1.323(3) . ?
O2 C1 1.237(3) . ?
C24 C23 1.429(4) . ?
C24 C15 1.409(4) . ?
C6 C7 1.474(3) . ?
C23 C18 1.407(4) . ?
C2 C1 1.471(4) . ?
C2 C3 1.343(4) . ?
C21 C20 1.413(4) . ?
C21 C22 1.499(4) . ?
C7 C8 1.350(4) . ?
C15 C16 1.432(4) . ?
C15 C14 1.399(4) . ?
C8 H8 0.9500 . ?
C8 C9 1.411(4) . ?
C16 H16 0.9500 . ?
C16 C17 1.333(4) . ?
C20 H20 0.9500 . ?
C20 C19 1.358(4) . ?
C18 C17 1.439(4) . ?
C18 C19 1.400(4) . ?
C5 H5 0.9500 . ?
C5 C4 1.332(4) . ?
C12 C13 1.406(4) . ?
C12 C11 1.497(4) . ?
C22 H22a 0.9800 . ?
C22 H22b 0.9800 . ?
C22 H22c 0.9800 . ?
C17 H17 0.9500 . ?
C13 H13 0.9500 . ?
C13 C14 1.366(4) . ?
C9 H9 0.9500 . ?
C9 C10 1.351(4) . ?
C14 H14 0.9500 . ?
C19 H19 0.9500 . ?
C10 H10 0.9500 . ?
C11 H11a 0.9800 . ?
C11 H11b 0.9800 . ?
C11 H11c 0.9800 . ?
C4 H4 0.9500 . ?
C4 C3 1.406(4) . ?
C3 H3 0.9500 . ?

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 O4 100.39(8) . . ?
N2 Zn1 O4 125.83(8) . . ?
N2 Zn1 O1 105.31(8) . . ?
N1 Zn1 O4 105.37(8) . . ?
N1 Zn1 O1 141.25(9) . . ?
N1 Zn1 N2 82.34(8) . . ?
C1 Zn1 O4 103.17(8) . . ?
C1 Zn1 O1 28.54(9) . . ?
C1 Zn1 N2 121.75(8) . . ?
C1 Zn1 N1 115.69(9) . . ?
C5 O3 C2 105.9(2) . . ?
C6 O4 Zn1 114.13(15) . . ?
C10 O6 C7 106.40(19) . . ?
C1 O1 Zn1 103.31(18) . . ?
C23 N2 Zn1 110.28(16) . . ?
C21 N2 Zn1 129.77(17) . . ?
C21 N2 C23 119.9(2) . . ?
C24 N1 Zn1 110.86(16) . . ?
C12 N1 Zn1 129.20(18) . . ?
C12 N1 C24 119.8(2) . . ?
C23 C24 N1 118.1(2) . . ?
C15 C24 N1 121.9(2) . . ?
C15 C24 C23 119.9(2) . . ?
O5 C6 O4 125.2(2) . . ?
C7 C6 O4 113.9(2) . . ?
C7 C6 O5 120.9(2) . . ?
C24 C23 N2 118.2(2) . . ?
C18 C23 N2 122.1(2) . . ?
C18 C23 C24 119.7(2) . . ?
C1 C2 O3 116.6(2) . . ?
C3 C2 O3 109.9(2) . . ?
C3 C2 C1 133.3(3) . . ?
C20 C21 N2 120.6(2) . . ?
C22 C21 N2 118.7(2) . . ?
C22 C21 C20 120.7(2) . . ?
C6 C7 O6 116.6(2) . . ?
C8 C7 O6 109.7(2) . . ?
C8 C7 C6 133.5(2) . . ?
C16 C15 C24 118.7(2) . . ?
C14 C15 C24 117.2(2) . . ?
C14 C15 C16 124.1(2) . . ?
O1 C1 Zn1 48.15(13) . . ?
O2 C1 Zn1 75.73(16) . . ?
O2 C1 O1 123.2(3) . . ?
C2 C1 Zn1 160.8(2) . . ?
C2 C1 O1 115.7(3) . . ?
C2 C1 O2 121.1(3) . . ?
H8 C8 C7 126.44(15) . . ?
C9 C8 C7 107.1(2) . . ?
C9 C8 H8 126.44(15) . . ?
H16 C16 C15 119.16(15) . . ?
C17 C16 C15 121.7(2) . . ?
C17 C16 H16 119.16(16) . . ?
H20 C20 C21 119.96(15) . . ?
C19 C20 C21 120.1(2) . . ?
C19 C20 H20 119.96(16) . . ?
C17 C18 C23 118.9(2) . . ?
C19 C18 C23 117.0(2) . . ?
C19 C18 C17 124.1(2) . . ?
H5 C5 O3 124.69(14) . . ?
C4 C5 O3 110.6(2) . . ?
C4 C5 H5 124.69(16) . . ?
C13 C12 N1 121.1(2) . . ?
C11 C12 N1 118.8(2) . . ?
C11 C12 C13 120.1(2) . . ?
H22a C22 C21 109.5 . . ?
H22b C22 C21 109.5 . . ?
H22b C22 H22a 109.5 . . ?
H22c C22 C21 109.5 . . ?
H22c C22 H22a 109.5 . . ?
H22c C22 H22b 109.5 . . ?
C18 C17 C16 121.1(2) . . ?
H17 C17 C16 119.46(16) . . ?
H17 C17 C18 119.46(16) . . ?
H13 C13 C12 120.03(16) . . ?
C14 C13 C12 119.9(3) . . ?
C14 C13 H13 120.03(16) . . ?
H9 C9 C8 126.86(15) . . ?
C10 C9 C8 106.3(2) . . ?
C10 C9 H9 126.86(16) . . ?
C13 C14 C15 119.9(2) . . ?
H14 C14 C15 120.03(16) . . ?
H14 C14 C13 120.03(16) . . ?
C18 C19 C20 120.3(2) . . ?
H19 C19 C20 119.84(16) . . ?
H19 C19 C18 119.84(15) . . ?
C9 C10 O6 110.5(2) . . ?
H10 C10 O6 124.77(14) . . ?
H10 C10 C9 124.77(16) . . ?
H11a C11 C12 109.5 . . ?
H11b C11 C12 109.5 . . ?
H11b C11 H11a 109.5 . . ?
H11c C11 C12 109.5 . . ?
H11c C11 H11a 109.5 . . ?
H11c C11 H11b 109.5 . . ?
H4 C4 C5 126.59(16) . . ?
C3 C4 C5 106.8(2) . . ?
C3 C4 H4 126.59(16) . . ?
C4 C3 C2 106.7(2) . . ?
H3 C3 C2 126.65(17) . . ?
H3 C3 C4 126.65(16) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Zn1 O4 C6 O5 4.58(19) . . . . ?
Zn1 O4 C6 C7 -176.53(15) . . . . ?
Zn1 O1 C1 O2 -11.15(18) . . . . ?
Zn1 O1 C1 C2 167.30(14) . . . . ?
Zn1 N2 C23 C24 2.50(17) . . . . ?
Zn1 N2 C23 C18 -177.86(15) . . . . ?
Zn1 N2 C21 C20 179.7(2) . . . . ?
Zn1 N2 C21 C22 1.4(2) . . . . ?
Zn1 N1 C24 C23 -2.54(18) . . . . ?
Zn1 N1 C24 C15 177.75(16) . . . . ?
Zn1 N1 C12 C13 -178.6(2) . . . . ?
Zn1 N1 C12 C11 -0.2(2) . . . . ?
Zn1 C1 C2 O3 -142.3(5) . . . . ?
Zn1 C1 C2 C3 31.6(6) . . . . ?
O3 C2 C1 O1 -172.1(2) . . . . ?
O3 C2 C1 O2 6.4(3) . . . . ?
O3 C2 C3 C4 0.4(2) . . . . ?
O3 C5 C4 C3 -0.5(2) . . . . ?
O4 C6 C7 O6 174.81(19) . . . . ?
O4 C6 C7 C8 -10.1(3) . . . . ?
O6 C7 C6 O5 -6.2(3) . . . . ?
O6 C7 C8 C9 0.3(2) . . . . ?
O6 C10 C9 C8 0.2(3) . . . . ?
O5 C6 C7 C8 168.9(2) . . . . ?
O1 C1 C2 C3 1.8(3) . . . . ?
N2 C23 C24 N1 0.0(3) . . . . ?
N2 C23 C24 C15 179.7(2) . . . . ?
N2 C23 C18 C17 178.8(2) . . . . ?
N2 C23 C18 C19 -2.2(3) . . . . ?
N2 C21 C20 C19 -1.9(3) . . . . ?
N1 C24 C23 C18 -179.6(2) . . . . ?
N1 C24 C15 C16 -179.2(2) . . . . ?
N1 C24 C15 C14 1.0(3) . . . . ?
N1 C12 C13 C14 2.0(3) . . . . ?
O2 C1 C2 C3 -179.8(3) . . . . ?
C24 C23 C18 C17 -1.6(3) . . . . ?
C24 C23 C18 C19 177.5(2) . . . . ?
C24 C15 C16 C17 -0.7(3) . . . . ?
C24 C15 C14 C13 -1.3(3) . . . . ?
C6 C7 C8 C9 -175.0(3) . . . . ?
C23 C18 C17 C16 2.0(3) . . . . ?
C23 C18 C19 C20 1.2(3) . . . . ?
C2 C3 C4 C5 0.1(3) . . . . ?
C21 C20 C19 C18 0.8(3) . . . . ?
C7 C8 C9 C10 -0.3(2) . . . . ?
C15 C16 C17 C18 -0.8(3) . . . . ?
C15 C14 C13 C12 -0.1(3) . . . . ?
C16 C17 C18 C19 -177.0(3) . . . . ?
C20 C19 C18 C17 -179.9(3) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'


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

data_4
_database_code_depnum_ccdc_archive 'CCDC 2112370'
loop_
_audit_author_name
_audit_author_address
'Petr Primakov'
;A N Nesmeyanov Institute of Organoelement Compounds of Russian Academy of Sciences
Russia
;
_audit_update_record             
;
2021-10-11 deposited with the CCDC.	2022-02-04 downloaded from the CCDC.
;
_audit_creation_date             2021-08-11
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_chemical_formula_moiety         'C18 H18 N2 O4 Zn'
_chemical_formula_sum            'C18 H18 N2 O4 Zn'
_chemical_formula_weight         391.750
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Zn 0.31207 1.46666 14.07430 7.03180 5.16520 2.41000 3.26550 0.23330 10.31630
58.70970 1.30410003662
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y,-z+1/2
3 -x,-y,-z
4 x,-y,z-1/2
5 x+1/2,y+1/2,z
6 -x+1/2,y+1/2,-z+1/2
7 -x+1/2,-y+1/2,-z
8 x+1/2,-y+1/2,z-1/2

_symmetry_Int_Tables_number      15
_cell_length_a                   14.561(4)
_cell_length_b                   9.318(2)
_cell_length_c                   25.811(6)
_cell_angle_alpha                90
_cell_angle_beta                 99.571(15)
_cell_angle_gamma                90
_cell_volume                     3453.4(14)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    5774
_cell_measurement_temperature    120
_cell_measurement_theta_max      30.49
_cell_measurement_theta_min      2.61
_exptl_absorpt_coefficient_mu    1.448
_exptl_absorpt_correction_T_max  0.4330
_exptl_absorpt_correction_T_min  0.2767
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.1142 before and 0.0662 after correction.
The Ratio of minimum to maximum transmission is 0.6390.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.507
_exptl_crystal_density_meas      .
_exptl_crystal_description       prism
_exptl_crystal_F_000             1619.407
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_diffrn_reflns_av_R_equivalents  0.0668
_diffrn_reflns_av_unetI/netI     0.0579
_diffrn_reflns_Laue_measured_fraction_full 0.9926
_diffrn_reflns_Laue_measured_fraction_max 0.9933
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            19728
_diffrn_reflns_point_group_measured_fraction_full 0.9926
_diffrn_reflns_point_group_measured_fraction_max 0.9933
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         2.66
_diffrn_ambient_temperature      120
_diffrn_measured_fraction_theta_full 0.9926
_diffrn_measured_fraction_theta_max 0.9933
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              18
_reflns_limit_h_min              -18
_reflns_limit_k_max              11
_reflns_limit_k_min              0
_reflns_limit_l_max              32
_reflns_limit_l_min              0
_reflns_number_gt                2921
_reflns_number_total             3729
_reflns_threshold_expression     I>=2u(I)
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.3 (Bourhis et al., 2015)'
_refine_diff_density_max         0.5319
_refine_diff_density_min         -0.6349
_refine_diff_density_rms         0.0878
_refine_ls_d_res_high            0.7829
_refine_ls_d_res_low             7.6695
_refine_ls_goodness_of_fit_ref   1.0458
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    30
_refine_ls_number_parameters     250
_refine_ls_number_reflns         3729
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0618
_refine_ls_R_factor_gt           0.0467
_refine_ls_restrained_S_all      1.0458
_refine_ls_shift/su_max          0.0001
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0467P)²+6.1882P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1119
_refine_ls_wR_factor_ref         0.1199
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Sof(O3a)=1-FVAR(1)
 Sof(O3)=FVAR(1)
 Sof(O4a)=1-FVAR(2)
 Sof(O4)=FVAR(2)
3.a Aromatic/amide H refined with riding coordinates:
 C14(H14), C13(H13), C10(H10), C8(H8), C11(H11), C7(H7)
3.b Idealised Me refined as rotating group:
 C4(H4a,H4b,H4c), C16(H16a,H16b,H16c), C6(H6a,H6b,H6c), C2(H2a,H2b,H2c)
;
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_refinement_flags_posn
_atom_site_disorder_group
Zn1 Zn 0.34765(2) 0.50683(4) 0.627324(14) 0.04236(14) Uani 1.000000 . .
N2 N 0.36375(16) 0.3993(3) 0.55782(9) 0.0372(5) Uani 1.000000 . .
O1 O 0.42833(18) 0.6503(3) 0.66294(13) 0.0738(8) Uani 1.000000 . .
O4 O 0.2306(8) 0.610(4) 0.5901(4) 0.074(4) Uani 0.75(13) . 1
N1 N 0.35515(17) 0.2964(3) 0.65483(10) 0.0405(6) Uani 1.000000 . .
O2 O 0.5392(2) 0.5281(4) 0.63691(14) 0.0902(10) Uani 1.000000 . .
O3 O 0.2204(13) 0.576(6) 0.6724(10) 0.107(7) Uani 0.50(8) . 1
C3 C 0.1863(2) 0.6115(4) 0.62687(14) 0.0477(8) Uani 1.000000 . .
C18 C 0.35692(19) 0.1995(3) 0.61558(12) 0.0379(6) Uani 1.000000 . .
C17 C 0.36193(19) 0.2541(3) 0.56411(12) 0.0372(6) Uani 1.000000 . .
C1 C 0.5124(3) 0.6309(4) 0.66014(14) 0.0538(8) Uani 1.000000 . .
C9 C 0.3554(2) 0.0506(4) 0.62397(13) 0.0460(7) Uani 1.000000 . .
C15 C 0.3701(2) 0.4530(4) 0.51139(13) 0.0431(7) Uani 1.000000 . .
C12 C 0.3657(2) 0.1581(3) 0.52258(12) 0.0443(7) Uani 1.000000 . .
C14 C 0.3749(2) 0.3631(4) 0.46769(13) 0.0514(8) Uani 1.000000 . .
H14 H 0.3800(2) 0.4037(4) 0.43453(13) 0.0617(10) Uiso 1.000000 R .
C5 C 0.3532(2) 0.2485(4) 0.70333(13) 0.0485(8) Uani 1.000000 . .
C13 C 0.3720(2) 0.2177(4) 0.47355(13) 0.0514(8) Uani 1.000000 . .
H13 H 0.3744(2) 0.1568(4) 0.44428(13) 0.0617(10) Uiso 1.000000 R .
C10 C 0.3578(3) -0.0443(4) 0.58035(16) 0.0570(9) Uani 1.000000 . .
H10 H 0.3552(3) -0.1451(4) 0.58550(16) 0.0684(11) Uiso 1.000000 R .
C4 C 0.0904(3) 0.6699(5) 0.62028(16) 0.0677(11) Uani 1.000000 . .
H4a H 0.0930(3) 0.7749(5) 0.6220(12) 0.1015(17) Uiso 1.000000 GR .
H4b H 0.0558(7) 0.640(3) 0.5861(5) 0.1015(17) Uiso 1.000000 GR .
H4c H 0.0590(7) 0.633(3) 0.6483(7) 0.1015(17) Uiso 1.000000 GR .
C8 C 0.3520(3) 0.0034(4) 0.67505(15) 0.0591(9) Uani 1.000000 . .
H8 H 0.3501(3) -0.0964(4) 0.68229(15) 0.0709(11) Uiso 1.000000 R .
C16 C 0.3740(3) 0.6129(4) 0.50593(14) 0.0579(9) Uani 1.000000 . .
H16a H 0.3139(6) 0.6545(4) 0.5102(10) 0.0868(14) Uiso 1.000000 GR .
H16b H 0.4230(12) 0.6516(5) 0.5329(7) 0.0868(14) Uiso 1.000000 GR .
H16c H 0.3876(18) 0.6373(4) 0.4711(4) 0.0868(14) Uiso 1.000000 GR .
C11 C 0.3635(3) 0.0073(4) 0.53227(15) 0.0559(9) Uani 1.000000 . .
H11 H 0.3661(3) -0.0578(4) 0.50424(15) 0.0670(10) Uiso 1.000000 R .
C7 C 0.3514(3) 0.0995(4) 0.71396(15) 0.0596(9) Uani 1.000000 . .
H7 H 0.3498(3) 0.0672(4) 0.74871(15) 0.0715(11) Uiso 1.000000 R .
C6 C 0.3547(3) 0.3576(4) 0.74597(14) 0.0695(11) Uani 1.000000 . .
H6a H 0.4176(6) 0.363(2) 0.7665(8) 0.1042(17) Uiso 1.000000 GR .
H6b H 0.337(2) 0.4514(8) 0.73036(15) 0.1042(17) Uiso 1.000000 GR .
H6c H 0.3108(16) 0.3293(18) 0.7690(7) 0.1042(17) Uiso 1.000000 GR .
C2 C 0.5802(3) 0.7368(5) 0.6886(2) 0.0900(15) Uani 1.000000 . .
H2a H 0.5591(14) 0.8345(5) 0.6790(12) 0.135(2) Uiso 1.000000 GR .
H2b H 0.584(2) 0.724(3) 0.7266(2) 0.135(2) Uiso 1.000000 GR .
H2c H 0.6417(7) 0.721(3) 0.6789(12) 0.135(2) Uiso 1.000000 GR .
O3a O 0.2201(11) 0.5341(19) 0.6615(11) 0.074(5) Uani 0.50(8) . 2
O4a O 0.230(3) 0.647(11) 0.5925(19) 0.077(10) Uani 0.25(13) . 2


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 N2 2.102(2) . ?
Zn1 O1 1.911(3) . ?
Zn1 O4 2.050(19) . ?
Zn1 N1 2.082(3) . ?
Zn1 O3 2.43(3) . ?
Zn1 O3a 2.199(19) . ?
Zn1 O4a 2.22(6) . ?
N2 C17 1.364(4) . ?
N2 C15 1.316(4) . ?
O1 C1 1.251(4) . ?
O4 C3 1.233(12) . ?
N1 C18 1.361(4) . ?
N1 C5 1.334(4) . ?
O2 C1 1.228(5) . ?
O3 C3 1.243(18) . ?
C3 C4 1.482(5) . ?
C3 O3a 1.189(17) . ?
C3 O4a 1.22(3) . ?
C18 C17 1.436(4) . ?
C18 C9 1.404(4) . ?
C17 C12 1.404(4) . ?
C1 C2 1.499(5) . ?
C9 C10 1.437(5) . ?
C9 C8 1.399(5) . ?
C15 C14 1.416(5) . ?
C15 C16 1.499(5) . ?
C12 C13 1.399(5) . ?
C12 C11 1.428(5) . ?
C14 H14 0.9500 . ?
C14 C13 1.365(5) . ?
C5 C7 1.416(5) . ?
C5 C6 1.495(5) . ?
C13 H13 0.9500 . ?
C10 H10 0.9500 . ?
C10 C11 1.347(5) . ?
C4 H4a 0.9800 . ?
C4 H4b 0.9800 . ?
C4 H4c 0.9800 . ?
C8 H8 0.9500 . ?
C8 C7 1.347(5) . ?
C16 H16a 0.9800 . ?
C16 H16b 0.9800 . ?
C16 H16c 0.9800 . ?
C11 H11 0.9500 . ?
C7 H7 0.9500 . ?
C6 H6a 0.9800 . ?
C6 H6b 0.9800 . ?
C6 H6c 0.9800 . ?
C2 H2a 0.9800 . ?
C2 H2b 0.9800 . ?
C2 H2c 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Zn1 N2 126.66(11) . . ?
O4 Zn1 N2 91.4(5) . . ?
O4 Zn1 O1 107.2(9) . . ?
N1 Zn1 N2 80.51(9) . . ?
N1 Zn1 O1 120.10(11) . . ?
N1 Zn1 O4 126.3(9) . . ?
O3 Zn1 N2 137.5(9) . . ?
O3 Zn1 O1 92.3(11) . . ?
O3 Zn1 O4 57.4(5) . . ?
O3 Zn1 N1 95.0(10) . . ?
O3a Zn1 N2 128.2(7) . . ?
O3a Zn1 O1 102.6(7) . . ?
O3a Zn1 O4 56.1(6) . . ?
O3a Zn1 N1 88.4(4) . . ?
O3a Zn1 O3 10.5(10) . . ?
O4a Zn1 N2 97(2) . . ?
O4a Zn1 O1 99(2) . . ?
O4a Zn1 O4 8(2) . . ?
O4a Zn1 N1 133.3(18) . . ?
O4a Zn1 O3 56.1(11) . . ?
O4a Zn1 O3a 56.6(9) . . ?
C17 N2 Zn1 111.37(19) . . ?
C15 N2 Zn1 129.1(2) . . ?
C15 N2 C17 119.4(3) . . ?
C1 O1 Zn1 113.6(2) . . ?
C3 O4 Zn1 98.4(10) . . ?
C18 N1 Zn1 112.2(2) . . ?
C5 N1 Zn1 128.8(2) . . ?
C5 N1 C18 118.9(3) . . ?
C3 O3 Zn1 80.4(13) . . ?
O3 C3 O4 123.2(13) . . ?
C4 C3 O4 121.3(9) . . ?
C4 C3 O3 115.3(13) . . ?
O3a C3 O4 111.5(16) . . ?
O3a C3 O3 22.7(18) . . ?
O3a C3 C4 125.0(9) . . ?
O4a C3 O4 17(4) . . ?
O4a C3 O3 126(2) . . ?
O4a C3 C4 115(3) . . ?
O4a C3 O3a 120(3) . . ?
C17 C18 N1 117.6(3) . . ?
C9 C18 N1 122.6(3) . . ?
C9 C18 C17 119.8(3) . . ?
C18 C17 N2 117.8(3) . . ?
C12 C17 N2 122.5(3) . . ?
C12 C17 C18 119.6(3) . . ?
O2 C1 O1 122.3(4) . . ?
C2 C1 O1 116.6(4) . . ?
C2 C1 O2 121.0(4) . . ?
C10 C9 C18 119.0(3) . . ?
C8 C9 C18 117.4(3) . . ?
C8 C9 C10 123.6(3) . . ?
C14 C15 N2 121.4(3) . . ?
C16 C15 N2 118.2(3) . . ?
C16 C15 C14 120.4(3) . . ?
C13 C12 C17 117.0(3) . . ?
C11 C12 C17 119.2(3) . . ?
C11 C12 C13 123.8(3) . . ?
H14 C14 C15 120.2(2) . . ?
C13 C14 C15 119.5(3) . . ?
C13 C14 H14 120.2(2) . . ?
C7 C5 N1 120.9(3) . . ?
C6 C5 N1 117.6(3) . . ?
C6 C5 C7 121.5(3) . . ?
C14 C13 C12 120.2(3) . . ?
H13 C13 C12 119.92(19) . . ?
H13 C13 C14 119.9(2) . . ?
H10 C10 C9 119.5(2) . . ?
C11 C10 C9 121.0(3) . . ?
C11 C10 H10 119.5(2) . . ?
H4a C4 C3 109.5 . . ?
H4b C4 C3 109.5 . . ?
H4b C4 H4a 109.5 . . ?
H4c C4 C3 109.5 . . ?
H4c C4 H4a 109.5 . . ?
H4c C4 H4b 109.5 . . ?
H8 C8 C9 120.0(2) . . ?
C7 C8 C9 120.0(3) . . ?
C7 C8 H8 120.0(2) . . ?
H16a C16 C15 109.5 . . ?
H16b C16 C15 109.5 . . ?
H16b C16 H16a 109.5 . . ?
H16c C16 C15 109.5 . . ?
H16c C16 H16a 109.5 . . ?
H16c C16 H16b 109.5 . . ?
C10 C11 C12 121.3(3) . . ?
H11 C11 C12 119.3(2) . . ?
H11 C11 C10 119.3(2) . . ?
C8 C7 C5 120.3(3) . . ?
H7 C7 C5 119.8(2) . . ?
H7 C7 C8 119.8(2) . . ?
H6a C6 C5 109.5 . . ?
H6b C6 C5 109.5 . . ?
H6b C6 H6a 109.5 . . ?
H6c C6 C5 109.5 . . ?
H6c C6 H6a 109.5 . . ?
H6c C6 H6b 109.5 . . ?
H2a C2 C1 109.5 . . ?
H2b C2 C1 109.5 . . ?
H2b C2 H2a 109.5 . . ?
H2c C2 C1 109.5 . . ?
H2c C2 H2a 109.5 . . ?
H2c C2 H2b 109.5 . . ?
C3 O3a Zn1 92.3(12) . . ?
C3 O4a Zn1 90(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 N2 C17 C18 -4.55(19) . . . . ?
Zn1 N2 C17 C12 176.10(19) . . . . ?
Zn1 N2 C15 C14 -175.9(3) . . . . ?
Zn1 N2 C15 C16 5.3(3) . . . . ?
Zn1 O1 C1 O2 -0.6(3) . . . . ?
Zn1 O1 C1 C2 -178.1(3) . . . . ?
Zn1 O4 C3 O3 9(4) . . . . ?
Zn1 O4 C3 C4 -176.9(3) . . . . ?
Zn1 O4 C3 O3a -13(2) . . . . ?
Zn1 O4 C3 O4a 113(5) . . . . ?
Zn1 N1 C18 C17 5.5(2) . . . . ?
Zn1 N1 C18 C9 -175.5(2) . . . . ?
Zn1 N1 C5 C7 174.7(3) . . . . ?
Zn1 N1 C5 C6 -6.4(3) . . . . ?
Zn1 O3 C3 O4 -8(3) . . . . ?
Zn1 O3 C3 C4 177.9(4) . . . . ?
Zn1 O3 C3 O3a 57.0(13) . . . . ?
Zn1 O3 C3 O4a -28(7) . . . . ?
Zn1 O3a C3 O4 12.0(18) . . . . ?
Zn1 O3a C3 O3 -113.7(18) . . . . ?
Zn1 O3a C3 C4 175.1(3) . . . . ?
Zn1 O3a C3 O4a -4(5) . . . . ?
Zn1 O4a C3 O4 -57(4) . . . . ?
Zn1 O4a C3 O3 30(7) . . . . ?
Zn1 O4a C3 C4 -175.3(5) . . . . ?
Zn1 O4a C3 O3a 4(5) . . . . ?
N2 C17 C18 N1 -0.6(3) . . . . ?
N2 C17 C18 C9 -179.6(3) . . . . ?
N2 C17 C12 C13 0.3(3) . . . . ?
N2 C17 C12 C11 180.0(3) . . . . ?
N2 C15 C14 C13 0.6(4) . . . . ?
N1 C18 C17 C12 178.8(3) . . . . ?
N1 C18 C9 C10 -179.8(3) . . . . ?
N1 C18 C9 C8 -0.0(3) . . . . ?
N1 C5 C7 C8 0.2(4) . . . . ?
C18 C17 C12 C13 -179.0(3) . . . . ?
C18 C17 C12 C11 0.7(3) . . . . ?
C18 C9 C10 C11 1.6(4) . . . . ?
C18 C9 C8 C7 -0.8(4) . . . . ?
C17 C12 C13 C14 0.4(3) . . . . ?
C17 C12 C11 C10 0.1(4) . . . . ?
C9 C10 C11 C12 -1.2(4) . . . . ?
C9 C8 C7 C5 0.7(5) . . . . ?
C15 C14 C13 C12 -0.8(4) . . . . ?

_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2

_olex2_submission_special_instructions 'No special instructions were received'

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

data_5
_database_code_depnum_ccdc_archive 'CCDC 2115090'
loop_
_audit_author_name
_audit_author_address
'Petr Primakov'
;A N Nesmeyanov Institute of Organoelement Compounds of Russian Academy of Sciences
Russia
;
_audit_update_record             
;
2021-10-11 deposited with the CCDC.	2022-02-04 downloaded from the CCDC.
;
_audit_creation_date             2021-09-30
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6403)
;
# start Validation Reply Form
_vrf_PLAT430_5                   
;
PROBLEM: Short Inter D...A Contact  O6       ..O6       .       2.74 Ang.  
RESPONSE: There is indeed a short O...O contact between the Fur fragments 
in crystal.
;
_chemical_formula_moiety         'C24 H20 Cu N2 O7, C5 H4 O3'
_chemical_formula_sum            'C29 H24 Cu N2 O10'
_chemical_formula_weight         624.067
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Cu 0.34125 1.28947 13.33800 7.16760 5.61580 1.67350 3.58280 0.24700 11.39660
64.81260 1.19099998474
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,-y,-z

_symmetry_Int_Tables_number      2
_cell_length_a                   10.7554(3)
_cell_length_b                   11.1284(3)
_cell_length_c                   12.4298(3)
_cell_angle_alpha                98.575(2)
_cell_angle_beta                 107.587(2)
_cell_angle_gamma                105.477(2)
_cell_volume                     1323.34(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1800
_cell_measurement_temperature    100
_cell_measurement_theta_max      24.25
_cell_measurement_theta_min      2.21
_exptl_absorpt_coefficient_mu    0.891
_exptl_absorpt_correction_T_max  0.3368
_exptl_absorpt_correction_T_min  0.2914
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0676 before and 0.0591 after correction.
The Ratio of minimum to maximum transmission is 0.8652.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            blue
_exptl_crystal_colour_primary    blue
_exptl_crystal_density_diffrn    1.566
_exptl_crystal_description       prism
_exptl_crystal_F_000             643.086
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_diffrn_reflns_av_R_equivalents  0.0953
_diffrn_reflns_av_unetI/netI     0.1503
_diffrn_reflns_Laue_measured_fraction_full 0.9944
_diffrn_reflns_Laue_measured_fraction_max 0.9948
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            19945
_diffrn_reflns_point_group_measured_fraction_full 0.9944
_diffrn_reflns_point_group_measured_fraction_max 0.9948
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         25.99
_diffrn_reflns_theta_min         1.96
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.9944
_diffrn_measured_fraction_theta_max 0.9948
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              12
_reflns_limit_h_min              -13
_reflns_limit_k_max              13
_reflns_limit_k_min              -13
_reflns_limit_l_max              15
_reflns_limit_l_min              0
_reflns_number_gt                3723
_reflns_number_total             5176
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.3 (Bourhis et al., 2015)'
_refine_diff_density_max         1.5498
_refine_diff_density_min         -1.7514
_refine_diff_density_rms         0.1724
_refine_ls_d_res_high            0.8108
_refine_ls_d_res_low             10.3841
_refine_ls_goodness_of_fit_ref   1.0591
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    50
_refine_ls_number_parameters     403
_refine_ls_number_reflns         5176
_refine_ls_number_restraints     38
_refine_ls_R_factor_all          0.0903
_refine_ls_R_factor_gt           0.0587
_refine_ls_restrained_S_all      1.0549
_refine_ls_shift/su_max          0.0001
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0453P)²+0.9300P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1177
_refine_ls_wR_factor_ref         0.1336
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 O3-C17
 2.225 with sigma of 0.02
 O3-C15
 1.365 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C17) \\sim Ueq, Uanis(C18) \\sim Ueq, Uanis(C16) \\sim Ueq: with sigma of
0.01 and sigma for terminal atoms of 0.02
Uanis(C18) \\sim Ueq, Uanis(C17) \\sim Ueq, Uanis(C16) \\sim Ueq: with sigma of
0.01 and sigma for terminal atoms of 0.02
Uanis(C33) = Uanis(O3)
Uanis(C32) = Uanis(C18)
Uanis(C17) = Uanis(O30)
4. Others
 Sof(H16)=Sof(C16)=Sof(H31)=Sof(C31)=Sof(H17)=Sof(C17)=Sof(O30)=1-FVAR(1)
 Sof(H33)=Sof(C33)=Sof(O3)=Sof(H32)=Sof(C32)=Sof(H18)=Sof(C18)=FVAR(1)
5.a Riding coordinates:
 O3(O7), O3(O10,H10b)
5.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C7(H7), C10(H10), C23(H23), C6(H6), C9(H9), C22(H22),
 C21(H21), C26(H26), C27(H27), C28(H28), C33(H33), C17(H17), C31(H31), C16(H16),
  C32(H32), C18(H18)
5.c Idealised Me refined as rotating group:
 C2(H2a,H2b,H2c), C29(H29a,H29b,H29c)
;
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_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_disorder_group
Cu1 Cu 0.31507(5) 0.87598(5) 0.56687(4) 0.01338(15) Uani 1.000000 . . .
O1 O 0.1956(3) 0.8081(3) 0.4001(2) 0.0164(6) Uani 1.000000 . . .
O4 O 0.4514(3) 0.9382(3) 0.7254(2) 0.0164(6) Uani 1.000000 . . .
O2 O 0.3630(3) 0.7804(3) 0.3365(2) 0.0201(7) Uani 1.000000 . . .
O5 O 0.6390(3) 0.9403(3) 0.6800(2) 0.0201(7) Uani 1.000000 . . .
O6 O 0.5979(3) 0.9889(3) 0.9535(2) 0.0198(7) Uani 1.000000 . . .
O9 O 0.3704(3) 0.4624(3) 0.8692(3) 0.0271(8) Uani 1.000000 . . .
N1 N 0.1416(3) 0.8985(3) 0.6252(3) 0.0138(7) Uani 1.000000 . . .
N2 N 0.2462(3) 0.7011(3) 0.5964(3) 0.0154(8) Uani 1.000000 . . .
O8 O 0.6727(3) 0.5225(3) 0.7963(3) 0.0372(9) Uani 1.000000 . . .
C19 C 0.5790(4) 0.9503(4) 0.7512(4) 0.0149(9) Uani 1.000000 . . .
C1 C 0.0912(4) 0.9950(4) 0.6386(3) 0.0160(9) Uani 1.000000 . . .
C20 C 0.6617(4) 0.9756(4) 0.8750(3) 0.0149(9) Uani 1.000000 . . .
C14 C 0.2417(4) 0.7796(4) 0.3202(4) 0.0153(9) Uani 1.000000 . . .
C12 C 0.1302(4) 0.6799(4) 0.6265(3) 0.0165(9) Uani 1.000000 . . .
C13 C 0.0732(4) 0.7827(4) 0.6372(3) 0.0157(9) Uani 1.000000 . . .
C15 C 0.1411(4) 0.7390(4) 0.1992(4) 0.0170(9) Uani 1.000000 D . .
C3 C -0.0360(4) 0.9760(4) 0.6551(4) 0.0193(10) Uani 1.000000 . . .
H3 H -0.0738(4) 1.0440(4) 0.6573(4) 0.0231(12) Uiso 1.000000 R . .
C8 C 0.0677(5) 0.5626(4) 0.6484(4) 0.0225(10) Uani 1.000000 . . .
C4 C -0.1053(4) 0.8597(4) 0.6680(4) 0.0223(10) Uani 1.000000 . . .
H4 H -0.1904(4) 0.8471(4) 0.6803(4) 0.0267(12) Uiso 1.000000 R . .
C5 C -0.0495(4) 0.7590(4) 0.6630(4) 0.0188(10) Uani 1.000000 . . .
C2 C 0.1753(4) 1.1271(4) 0.6404(4) 0.0217(10) Uani 1.000000 . . .
H2a H 0.236(2) 1.1731(10) 0.7207(5) 0.0326(15) Uiso 1.000000 GR . .
H2b H 0.231(2) 1.1199(4) 0.5920(19) 0.0326(15) Uiso 1.000000 GR . .
H2c H 0.1135(4) 1.1745(10) 0.610(2) 0.0326(15) Uiso 1.000000 GR . .
C11 C 0.3010(4) 0.6075(4) 0.5873(4) 0.0209(10) Uani 1.000000 . . .
C16 C 0.0209(16) 0.6672(13) 0.0116(11) 0.018(3) Uani 0.463(4) . U 2
C7 C -0.0531(5) 0.5444(4) 0.6779(4) 0.0248(11) Uani 1.000000 . . .
H7 H -0.0942(5) 0.4652(4) 0.6933(4) 0.0298(13) Uiso 1.000000 R . .
C24 C 0.5660(4) 0.4646(4) 0.8049(4) 0.0212(10) Uani 1.000000 . . .
C10 C 0.2420(5) 0.4880(4) 0.6073(4) 0.0235(10) Uani 1.000000 . . .
H10 H 0.2822(5) 0.4223(4) 0.5997(4) 0.0282(12) Uiso 1.000000 R . .
C23 C 0.6932(5) 1.0052(4) 1.0603(4) 0.0251(11) Uani 1.000000 . . .
H23 H 0.6770(5) 1.0175(4) 1.1315(4) 0.0301(13) Uiso 1.000000 R . .
C25 C 0.4875(5) 0.5316(4) 0.8541(4) 0.0223(10) Uani 1.000000 . . .
C29 C 0.4253(5) 0.6317(5) 0.5531(4) 0.0266(11) Uani 1.000000 . . .
H29a H 0.3978(6) 0.588(2) 0.4709(8) 0.0400(16) Uiso 1.000000 GR . .
H29b H 0.4678(18) 0.7245(5) 0.565(2) 0.0400(16) Uiso 1.000000 GR . .
H29c H 0.4920(13) 0.598(2) 0.6014(17) 0.0400(16) Uiso 1.000000 GR . .
C6 C -0.1103(5) 0.6399(5) 0.6842(4) 0.0261(11) Uani 1.000000 . . .
H6 H -0.1914(5) 0.6263(5) 0.7030(4) 0.0314(13) Uiso 1.000000 R . .
C9 C 0.1277(5) 0.4655(4) 0.6376(4) 0.0279(11) Uani 1.000000 . . .
H9 H 0.0887(5) 0.3846(4) 0.6513(4) 0.0334(14) Uiso 1.000000 R . .
C22 C 0.8138(5) 1.0014(5) 1.0508(4) 0.0293(12) Uani 1.000000 . . .
H22 H 0.8959(5) 1.0094(5) 1.1123(4) 0.0351(14) Uiso 1.000000 R . .
C21 C 0.7935(4) 0.9830(5) 0.9307(4) 0.0256(11) Uani 1.000000 . . .
H21 H 0.8599(4) 0.9771(5) 0.8961(4) 0.0308(13) Uiso 1.000000 R . .
C26 C 0.5105(5) 0.6575(5) 0.8876(4) 0.0290(11) Uani 1.000000 . . .
H26 H 0.5849(5) 0.7248(5) 0.8853(4) 0.0348(14) Uiso 1.000000 R . .
C27 C 0.4051(5) 0.6726(5) 0.9266(5) 0.0352(13) Uani 1.000000 . . .
H27 H 0.3943(5) 0.7513(5) 0.9565(5) 0.0422(15) Uiso 1.000000 R . .
C28 C 0.3217(5) 0.5524(5) 0.9131(4) 0.0323(12) Uani 1.000000 . . .
H28 H 0.2403(5) 0.5331(5) 0.9317(4) 0.0388(15) Uiso 1.000000 R . .
C18 C -0.0276(14) 0.6910(10) 0.0260(10) 0.0252(19) Uani 0.537(4) . U 1
C17 C 0.1908(19) 0.720(2) 0.109(2) 0.029(2) Uani 0.463(4) D U 1
O3 O 0.0052(2) 0.7326(2) 0.15084(18) 0.020(2) Uani 0.537(4) D . 1
H7a H 0.564(6) 0.308(6) 0.740(6) 0.09(2) Uiso 1.000000 . . .
O7 O 0.5096(2) 0.3384(2) 0.77330(18) 0.0292(8) Uani 1.000000 R . .
H10a H 0.475(5) 1.090(4) 0.572(4) 0.030(14) Uiso 1.000000 . . .
O10 O 0.3895(2) 1.0406(2) 0.53451(18) 0.0173(7) Uani 1.000000 R . .
H10b H 0.3332(2) 1.0550(2) 0.47689(18) 0.13(3) Uiso 1.000000 R . .
C33 C 0.0125(10) 0.7462(10) 0.1950(10) 0.020(2) Uani 0.537(4) . . 2
C31 C 0.0818(15) 0.6867(13) 0.0078(11) 0.031(3) Uani 0.463(4) . . 1
C32 C -0.0620(11) 0.7035(10) 0.0674(10) 0.0252(19) Uani 0.537(4) . . 2
O30 O 0.1615(13) 0.6950(14) 0.1009(14) 0.029(2) Uani 0.463(4) . . 2
H33 H -0.0183(10) 0.7712(10) 0.2561(10) 0.024(2) Uiso 0.537(4) R . 2
H17 H 0.2836(19) 0.728(2) 0.117(2) 0.035(3) Uiso 0.463(4) R . 1
H31 H 0.0862(15) 0.6633(13) -0.0674(11) 0.037(4) Uiso 0.463(4) R . 1
H16 H -0.0068(16) 0.6309(13) -0.0696(11) 0.022(4) Uiso 0.463(4) R . 2
H32 H -0.1539(11) 0.7012(10) 0.0290(10) 0.030(2) Uiso 0.537(4) R . 2
H18 H -0.1161(14) 0.6703(10) -0.0324(10) 0.030(2) Uiso 0.537(4) R . 1


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 O1 1.981(3) . ?
Cu1 O4 1.954(3) . ?
Cu1 N1 2.254(3) . ?
Cu1 N2 2.019(3) . ?
Cu1 O10 1.947(2) . ?
O1 C14 1.272(5) . ?
O4 C19 1.276(5) . ?
O2 C14 1.255(5) . ?
O5 C19 1.251(5) . ?
O6 C20 1.365(5) . ?
O6 C23 1.361(5) . ?
O9 C25 1.372(5) . ?
O9 C28 1.366(5) . ?
N1 C1 1.337(5) . ?
N1 C13 1.357(5) . ?
N2 C12 1.379(5) . ?
N2 C11 1.335(5) . ?
O8 C24 1.201(5) . ?
C19 C20 1.465(5) . ?
C1 C3 1.410(6) . ?
C1 C2 1.499(6) . ?
C20 C21 1.350(6) . ?
C14 C15 1.480(5) . ?
C12 C13 1.442(6) . ?
C12 C8 1.407(6) . ?
C13 C5 1.418(6) . ?
C15 C17 1.39(2) . ?
C15 O3 1.379(4) . ?
C15 C33 1.392(11) . ?
C15 O30 1.350(14) . ?
C3 H3 0.9500 . ?
C3 C4 1.370(6) . ?
C8 C7 1.426(6) . ?
C8 C9 1.409(6) . ?
C4 H4 0.9500 . ?
C4 C5 1.408(6) . ?
C5 C6 1.414(6) . ?
C2 H2a 0.9800 . ?
C2 H2b 0.9800 . ?
C2 H2c 0.9800 . ?
C11 C10 1.406(6) . ?
C11 C29 1.491(6) . ?
C16 C32 1.385(16) . ?
C16 O30 1.50(2) . ?
C16 H16 0.9500 . ?
C7 H7 0.9500 . ?
C7 C6 1.366(6) . ?
C24 C25 1.468(6) . ?
C24 O7 1.315(5) . ?
C10 H10 0.9500 . ?
C10 C9 1.363(6) . ?
C23 H23 0.9500 . ?
C23 C22 1.349(6) . ?
C25 C26 1.333(6) . ?
C29 H29a 0.9800 . ?
C29 H29b 0.9800 . ?
C29 H29c 0.9800 . ?
C6 H6 0.9500 . ?
C9 H9 0.9500 . ?
C22 H22 0.9500 . ?
C22 C21 1.416(6) . ?
C21 H21 0.9500 . ?
C26 H26 0.9500 . ?
C26 C27 1.399(7) . ?
C27 H27 0.9500 . ?
C27 C28 1.350(7) . ?
C28 H28 0.9500 . ?
C18 O3 1.454(12) . ?
C18 C31 1.275(17) . ?
C18 H18 0.9500 . ?
C17 C31 1.35(3) . ?
C17 H17 0.9500 . ?
H7a O7 0.91(6) . ?
H10a O10 0.87(5) . ?
O10 H10b 0.8537 . ?
C33 C32 1.480(12) . ?
C33 H33 0.9500 . ?
C31 H31 0.9500 . ?
C32 H32 0.9500 . ?

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 Cu1 O1 172.74(11) . . ?
N1 Cu1 O1 94.01(11) . . ?
N1 Cu1 O4 93.20(11) . . ?
N2 Cu1 O1 90.55(13) . . ?
N2 Cu1 O4 90.00(13) . . ?
N2 Cu1 N1 79.78(13) . . ?
O10 Cu1 O1 88.84(10) . . ?
O10 Cu1 O4 90.16(11) . . ?
O10 Cu1 N1 103.86(11) . . ?
O10 Cu1 N2 176.35(12) . . ?
C14 O1 Cu1 122.8(3) . . ?
C19 O4 Cu1 124.2(3) . . ?
C23 O6 C20 106.5(3) . . ?
C28 O9 C25 105.2(4) . . ?
C1 N1 Cu1 133.2(3) . . ?
C13 N1 Cu1 108.0(3) . . ?
C13 N1 C1 118.5(4) . . ?
C12 N2 Cu1 114.9(3) . . ?
C11 N2 Cu1 126.0(3) . . ?
C11 N2 C12 119.2(4) . . ?
O5 C19 O4 125.7(4) . . ?
C20 C19 O4 117.0(3) . . ?
C20 C19 O5 117.3(4) . . ?
C3 C1 N1 121.6(4) . . ?
C2 C1 N1 118.7(4) . . ?
C2 C1 C3 119.7(4) . . ?
C19 C20 O6 117.8(3) . . ?
C21 C20 O6 109.9(4) . . ?
C21 C20 C19 132.3(4) . . ?
O2 C14 O1 125.4(4) . . ?
C15 C14 O1 116.1(4) . . ?
C15 C14 O2 118.4(4) . . ?
C13 C12 N2 118.4(4) . . ?
C8 C12 N2 122.2(4) . . ?
C8 C12 C13 119.4(4) . . ?
C12 C13 N1 118.5(4) . . ?
C5 C13 N1 123.1(4) . . ?
C5 C13 C12 118.4(4) . . ?
C17 C15 C14 117.7(10) . . ?
O3 C15 C14 133.5(4) . . ?
O3 C15 C17 108.0(10) . . ?
C33 C15 C14 111.8(6) . . ?
C33 C15 C17 129.7(11) . . ?
C33 C15 O3 21.8(5) . . ?
O30 C15 C14 127.4(7) . . ?
O30 C15 C17 13.9(12) . . ?
O30 C15 O3 99.1(7) . . ?
O30 C15 C33 120.8(8) . . ?
H3 C3 C1 120.0(2) . . ?
C4 C3 C1 120.1(4) . . ?
C4 C3 H3 120.0(2) . . ?
C7 C8 C12 120.2(4) . . ?
C9 C8 C12 117.3(4) . . ?
C9 C8 C7 122.5(4) . . ?
H4 C4 C3 120.3(2) . . ?
C5 C4 C3 119.5(4) . . ?
C5 C4 H4 120.3(3) . . ?
C4 C5 C13 116.8(4) . . ?
C6 C5 C13 120.8(4) . . ?
C6 C5 C4 122.3(4) . . ?
H2a C2 C1 109.5 . . ?
H2b C2 C1 109.5 . . ?
H2b C2 H2a 109.5 . . ?
H2c C2 C1 109.5 . . ?
H2c C2 H2a 109.5 . . ?
H2c C2 H2b 109.5 . . ?
C10 C11 N2 121.0(4) . . ?
C29 C11 N2 118.4(4) . . ?
C29 C11 C10 120.6(4) . . ?
O30 C16 C32 108.5(11) . . ?
H16 C16 C32 125.7(8) . . ?
H16 C16 O30 125.7(8) . . ?
H7 C7 C8 119.7(3) . . ?
C6 C7 C8 120.6(4) . . ?
C6 C7 H7 119.7(3) . . ?
C25 C24 O8 121.5(4) . . ?
O7 C24 O8 124.4(4) . . ?
O7 C24 C25 114.0(4) . . ?
H10 C10 C11 119.7(3) . . ?
C9 C10 C11 120.7(4) . . ?
C9 C10 H10 119.7(3) . . ?
H23 C23 O6 124.8(2) . . ?
C22 C23 O6 110.5(4) . . ?
C22 C23 H23 124.8(3) . . ?
C24 C25 O9 120.2(4) . . ?
C26 C25 O9 110.4(4) . . ?
C26 C25 C24 129.5(4) . . ?
H29a C29 C11 109.5 . . ?
H29b C29 C11 109.5 . . ?
H29b C29 H29a 109.5 . . ?
H29c C29 C11 109.5 . . ?
H29c C29 H29a 109.5 . . ?
H29c C29 H29b 109.5 . . ?
C7 C6 C5 120.4(4) . . ?
H6 C6 C5 119.8(3) . . ?
H6 C6 C7 119.8(3) . . ?
C10 C9 C8 119.7(4) . . ?
H9 C9 C8 120.1(3) . . ?
H9 C9 C10 120.1(3) . . ?
H22 C22 C23 126.9(3) . . ?
C21 C22 C23 106.2(4) . . ?
C21 C22 H22 126.9(2) . . ?
C22 C21 C20 106.9(4) . . ?
H21 C21 C20 126.6(3) . . ?
H21 C21 C22 126.6(2) . . ?
H26 C26 C25 126.2(3) . . ?
C27 C26 C25 107.6(4) . . ?
C27 C26 H26 126.2(3) . . ?
H27 C27 C26 127.0(3) . . ?
C28 C27 C26 106.0(4) . . ?
C28 C27 H27 127.0(3) . . ?
C27 C28 O9 110.7(4) . . ?
H28 C28 O9 124.6(3) . . ?
H28 C28 C27 124.6(3) . . ?
C31 C18 O3 108.9(10) . . ?
H18 C18 O3 125.5(6) . . ?
H18 C18 C31 125.5(8) . . ?
C31 C17 C15 107.0(14) . . ?
H17 C17 C15 126.5(9) . . ?
H17 C17 C31 126.5(9) . . ?
C18 O3 C15 104.0(6) . . ?
H7a O7 C24 106(4) . . ?
H10a O10 Cu1 122(3) . . ?
H10b O10 Cu1 113.58(6) . . ?
H10b O10 H10a 124(3) . . ?
C32 C33 C15 99.3(9) . . ?
H33 C33 C15 130.3(5) . . ?
H33 C33 C32 130.3(6) . . ?
C17 C31 C18 111.5(13) . . ?
H31 C31 C18 124.3(8) . . ?
H31 C31 C17 124.3(9) . . ?
C33 C32 C16 110.6(10) . . ?
H32 C32 C16 124.7(8) . . ?
H32 C32 C33 124.7(6) . . ?
C16 O30 C15 100.6(10) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cu1 O1 C14 O2 6.0(3) . . . . ?
Cu1 O1 C14 C15 -175.7(3) . . . . ?
Cu1 O4 C19 O5 9.6(3) . . . . ?
Cu1 O4 C19 C20 -169.2(3) . . . . ?
Cu1 N1 C1 C3 167.5(4) . . . . ?
Cu1 N1 C1 C2 -14.8(4) . . . . ?
Cu1 N1 C13 C12 7.5(3) . . . . ?
Cu1 N1 C13 C5 -174.3(2) . . . . ?
Cu1 N2 C12 C13 -1.8(3) . . . . ?
Cu1 N2 C12 C8 179.1(3) . . . . ?
Cu1 N2 C11 C10 -178.4(3) . . . . ?
Cu1 N2 C11 C29 0.5(4) . . . . ?
O1 C14 C15 C17 173.6(12) . . . . ?
O1 C14 C15 O3 5.1(5) . . . . ?
O1 C14 C15 C33 3.2(6) . . . . ?
O1 C14 C15 O30 -174.6(9) . . . . ?
O4 C19 C20 O6 -2.3(4) . . . . ?
O4 C19 C20 C21 173.9(4) . . . . ?
O2 C14 C15 C17 -8.0(12) . . . . ?
O2 C14 C15 O3 -176.5(3) . . . . ?
O2 C14 C15 C33 -178.5(6) . . . . ?
O2 C14 C15 O30 3.8(9) . . . . ?
O5 C19 C20 O6 178.8(4) . . . . ?
O5 C19 C20 C21 -4.9(5) . . . . ?
O6 C20 C21 C22 0.4(4) . . . . ?
O6 C23 C22 C21 0.7(4) . . . . ?
O9 C25 C24 O8 -176.1(4) . . . . ?
O9 C25 C24 O7 3.4(4) . . . . ?
O9 C25 C26 C27 0.2(4) . . . . ?
O9 C28 C27 C26 0.9(5) . . . . ?
N1 C1 C3 C4 5.8(5) . . . . ?
N1 C13 C12 N2 -4.5(4) . . . . ?
N1 C13 C12 C8 174.6(4) . . . . ?
N1 C13 C5 C4 4.4(5) . . . . ?
N1 C13 C5 C6 -174.6(4) . . . . ?
N2 C12 C13 C5 177.2(4) . . . . ?
N2 C12 C8 C7 -179.3(4) . . . . ?
N2 C12 C8 C9 -0.5(5) . . . . ?
N2 C11 C10 C9 -0.6(5) . . . . ?
O8 C24 C25 C26 5.1(6) . . . . ?
C19 C20 C21 C22 -176.1(6) . . . . ?
C1 C3 C4 C5 -0.9(5) . . . . ?
C20 C21 C22 C23 -0.6(4) . . . . ?
C14 C15 C17 C31 -178.5(15) . . . . ?
C14 C15 O3 C18 176.9(6) . . . . ?
C14 C15 C33 C32 179.1(7) . . . . ?
C14 C15 O30 C16 178.0(12) . . . . ?
C12 C13 C5 C4 -177.5(4) . . . . ?
C12 C13 C5 C6 3.5(5) . . . . ?
C12 C8 C7 C6 0.6(5) . . . . ?
C12 C8 C9 C10 0.2(5) . . . . ?
C13 C5 C4 C3 -3.8(4) . . . . ?
C13 C5 C6 C7 -1.3(5) . . . . ?
C15 C17 C31 C18 3.7(19) . . . . ?
C15 O3 C18 C31 -5.4(7) . . . . ?
C15 C33 C32 C16 4.5(9) . . . . ?
C15 O30 C16 C32 2.6(12) . . . . ?
C3 C4 C5 C6 175.2(4) . . . . ?
C8 C7 C6 C5 -0.8(5) . . . . ?
C8 C9 C10 C11 0.3(5) . . . . ?
C4 C5 C6 C7 179.7(4) . . . . ?
C24 C25 C26 C27 179.0(6) . . . . ?
C25 C26 C27 C28 -0.6(5) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
loop_
_restr_distance_atom_site_label_1
_restr_distance_atom_site_label_2
_restr_distance_site_symmetry_2
_restr_distance_target
_restr_distance_target_weight_param
_restr_distance_diff
O3 C15 1 1.3650 0.0200 -0.0140
O3 C17 1 2.2250 0.0200 -0.0193

loop_
_restr_U_iso_atom_site_label
_restr_U_iso_weight_param
C16 0.0100
C16 0.0100
C18 0.0100
C18 0.0100
C17 0.0100
C17 0.0100




