# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_aa
_audit_block_doi                 10.5517/ccdc.csd.cc229cxp
_database_code_depnum_ccdc_archive 'CCDC 1915642'
loop_
_audit_author_name
_audit_author_address
Co
;The Cambidge Crystallographic Data Centre
China
;
_audit_update_record             
;
2019-05-11 deposited with the CCDC.	2020-01-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H18 Co N2 O3'
_chemical_formula_weight         393.29

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_H-M_alt        'P b c n'
_space_group_name_Hall           '-P 2n 2ab'

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

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

_cell_length_a                   7.2787(16)
_cell_length_b                   9.128(2)
_cell_length_c                   25.164(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1671.8(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1555
_cell_measurement_theta_min      3.24
_cell_measurement_theta_max      23.47

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.563
_exptl_crystal_F_000             812
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.280
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    1.050
_shelx_estimated_absorpt_T_min   0.744
_shelx_estimated_absorpt_T_max   0.834
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(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            8606
_diffrn_reflns_av_unetI/netI     0.0667
_diffrn_reflns_av_R_equivalents  0.1132
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         1.618
_diffrn_reflns_theta_max         25.013
_diffrn_reflns_theta_full        25.013
_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             1475
_reflns_number_gt                1028
_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    'SHELXT 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_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)+(0.0508P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1475
_refine_ls_number_parameters     124
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0629
_refine_ls_R_factor_gt           0.0415
_refine_ls_wR_factor_ref         0.1042
_refine_ls_wR_factor_gt          0.0937
_refine_ls_goodness_of_fit_ref   0.985
_refine_ls_restrained_S_all      0.985
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Co1 Co 0.500000 0.69998(6) 0.750000 0.0229(2) Uani 1 2 d S T P . .
O1 O 0.2885(3) 0.5978(2) 0.71545(8) 0.0276(5) Uani 1 1 d . . . . .
O2 O 0.500000 0.9298(3) 0.750000 0.0314(8) Uani 1 2 d DS T P . .
N1 N 0.5939(3) 0.6998(3) 0.67020(9) 0.0240(6) Uani 1 1 d . . . . .
C1 C 0.4613(4) 0.6453(3) 0.63746(12) 0.0246(7) Uani 1 1 d . . . . .
C6 C 0.4809(4) 0.6411(4) 0.58140(13) 0.0301(8) Uani 1 1 d . . . . .
C2 C 0.2999(4) 0.5892(3) 0.66265(12) 0.0249(7) Uani 1 1 d . . . . .
C9 C 0.7484(4) 0.7522(4) 0.64988(12) 0.0286(8) Uani 1 1 d . . . . .
C3 C 0.1659(4) 0.5301(4) 0.63039(12) 0.0343(8) Uani 1 1 d . . . . .
H3 H 0.059573 0.492436 0.645644 0.041 Uiso 1 1 calc R U . . .
C7 C 0.6457(5) 0.7001(4) 0.56081(13) 0.0383(9) Uani 1 1 d . . . . .
H7 H 0.665375 0.701648 0.524301 0.046 Uiso 1 1 calc R U . . .
C8 C 0.7750(5) 0.7544(4) 0.59408(13) 0.0393(9) Uani 1 1 d . . . . .
H8 H 0.882645 0.793718 0.580149 0.047 Uiso 1 1 calc R U . . .
C10 C 0.8899(4) 0.8106(4) 0.68698(13) 0.0373(9) Uani 1 1 d . . . . .
H10A H 0.848268 0.901902 0.701619 0.056 Uiso 1 1 calc R U . . .
H10B H 1.002778 0.826027 0.668059 0.056 Uiso 1 1 calc R U . . .
H10C H 0.909860 0.741633 0.715194 0.056 Uiso 1 1 calc R U . . .
C5 C 0.3384(5) 0.5802(4) 0.55050(13) 0.0388(9) Uani 1 1 d . . . . .
H5 H 0.348265 0.577458 0.513662 0.047 Uiso 1 1 calc R U . . .
C4 C 0.1870(5) 0.5257(4) 0.57478(12) 0.0386(9) Uani 1 1 d . . . . .
H4 H 0.094556 0.484221 0.554185 0.046 Uiso 1 1 calc R U . . .
H2 H 0.411(3) 0.985(3) 0.7414(12) 0.042(10) Uiso 1 1 d D . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Co1 O1 1.999(2) 3_656 ?
Co1 O1 1.999(2) . ?
Co1 O2 2.098(3) . ?
Co1 N1 2.121(2) . ?
Co1 N1 2.121(2) 3_656 ?
O1 C2 1.334(3) . ?
O2 H2 0.849(10) . ?
O2 H2 0.849(10) 3_656 ?
N1 C9 1.325(4) . ?
N1 C1 1.362(4) . ?
C1 C6 1.418(4) . ?
C1 C2 1.430(4) . ?
C6 C5 1.411(4) . ?
C6 C7 1.414(4) . ?
C2 C3 1.378(4) . ?
C9 C8 1.418(4) . ?
C9 C10 1.489(4) . ?
C3 C4 1.408(4) . ?
C3 H3 0.9300 . ?
C7 C8 1.354(5) . ?
C7 H7 0.9300 . ?
C8 H8 0.9300 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C5 C4 1.354(5) . ?
C5 H5 0.9300 . ?
C4 H4 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Co1 O1 124.37(13) 3_656 . ?
O1 Co1 O2 117.81(6) 3_656 . ?
O1 Co1 O2 117.81(6) . . ?
O1 Co1 N1 99.40(9) 3_656 . ?
O1 Co1 N1 80.56(9) . . ?
O2 Co1 N1 90.04(7) . . ?
O1 Co1 N1 80.56(9) 3_656 3_656 ?
O1 Co1 N1 99.40(9) . 3_656 ?
O2 Co1 N1 90.04(7) . 3_656 ?
N1 Co1 N1 179.91(14) . 3_656 ?
C2 O1 Co1 114.41(18) . . ?
Co1 O2 H2 126(2) . . ?
Co1 O2 H2 126(2) . 3_656 ?
H2 O2 H2 108(5) . 3_656 ?
C9 N1 C1 120.0(3) . . ?
C9 N1 Co1 129.7(2) . . ?
C1 N1 Co1 110.16(19) . . ?
N1 C1 C6 122.7(3) . . ?
N1 C1 C2 116.4(3) . . ?
C6 C1 C2 120.9(3) . . ?
C5 C6 C7 124.9(3) . . ?
C5 C6 C1 119.0(3) . . ?
C7 C6 C1 116.1(3) . . ?
O1 C2 C3 124.5(3) . . ?
O1 C2 C1 118.1(3) . . ?
C3 C2 C1 117.4(3) . . ?
N1 C9 C8 120.2(3) . . ?
N1 C9 C10 118.3(3) . . ?
C8 C9 C10 121.4(3) . . ?
C2 C3 C4 121.3(3) . . ?
C2 C3 H3 119.4 . . ?
C4 C3 H3 119.4 . . ?
C8 C7 C6 120.2(3) . . ?
C8 C7 H7 119.9 . . ?
C6 C7 H7 119.9 . . ?
C7 C8 C9 120.8(3) . . ?
C7 C8 H8 119.6 . . ?
C9 C8 H8 119.6 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C4 C5 C6 119.6(3) . . ?
C4 C5 H5 120.2 . . ?
C6 C5 H5 120.2 . . ?
C5 C4 C3 121.8(3) . . ?
C5 C4 H4 119.1 . . ?
C3 C4 H4 119.1 . . ?

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
C9 N1 C1 C6 0.3(5) . . . . ?
Co1 N1 C1 C6 175.7(2) . . . . ?
C9 N1 C1 C2 179.2(3) . . . . ?
Co1 N1 C1 C2 -5.4(3) . . . . ?
N1 C1 C6 C5 178.8(3) . . . . ?
C2 C1 C6 C5 -0.1(5) . . . . ?
N1 C1 C6 C7 -1.4(5) . . . . ?
C2 C1 C6 C7 179.7(3) . . . . ?
Co1 O1 C2 C3 -176.7(3) . . . . ?
Co1 O1 C2 C1 3.1(3) . . . . ?
N1 C1 C2 O1 1.8(4) . . . . ?
C6 C1 C2 O1 -179.3(3) . . . . ?
N1 C1 C2 C3 -178.4(3) . . . . ?
C6 C1 C2 C3 0.6(5) . . . . ?
C1 N1 C9 C8 1.2(5) . . . . ?
Co1 N1 C9 C8 -173.2(2) . . . . ?
C1 N1 C9 C10 -180.0(3) . . . . ?
Co1 N1 C9 C10 5.6(4) . . . . ?
O1 C2 C3 C4 179.6(3) . . . . ?
C1 C2 C3 C4 -0.2(5) . . . . ?
C5 C6 C7 C8 -179.2(3) . . . . ?
C1 C6 C7 C8 1.0(5) . . . . ?
C6 C7 C8 C9 0.5(6) . . . . ?
N1 C9 C8 C7 -1.6(5) . . . . ?
C10 C9 C8 C7 179.6(3) . . . . ?
C7 C6 C5 C4 179.5(3) . . . . ?
C1 C6 C5 C4 -0.7(5) . . . . ?
C6 C5 C4 C3 1.1(6) . . . . ?
C2 C3 C4 C5 -0.6(6) . . . . ?

_refine_diff_density_max         0.329
_refine_diff_density_min         -0.675
_refine_diff_density_rms         0.083

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

data_aaa
_database_code_depnum_ccdc_archive 'CCDC 1915924'
loop_
_audit_author_name
_audit_author_address
Zn
;The Cambridge Crystallographic Data Cemtre
China
;
_audit_update_record             
;
2019-05-14 deposited with the CCDC.	2020-01-08 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            'C20 H18 Co0 N2 O3 Zn'
_chemical_formula_weight         399.73

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_H-M_alt        'P b c n'
_space_group_name_Hall           '-P 2n 2ab'

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

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

_cell_length_a                   7.225(3)
_cell_length_b                   9.060(4)
_cell_length_c                   25.026(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1638.2(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2898
_cell_measurement_theta_min      3.26
_cell_measurement_theta_max      27.46

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.621
_exptl_crystal_F_000             824
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    1.523
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(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            9607
_diffrn_reflns_av_unetI/netI     0.0554
_diffrn_reflns_av_R_equivalents  0.0732
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         3.256
_diffrn_reflns_theta_max         27.528
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             1867
_reflns_number_gt                1457
_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)+(0.0730P)²+2.1690P] 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         1867
_refine_ls_number_parameters     120
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0668
_refine_ls_R_factor_gt           0.0479
_refine_ls_wR_factor_ref         0.1374
_refine_ls_wR_factor_gt          0.1266
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_restrained_S_all      1.062
_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 0.5000 0.69557(5) 0.7500 0.0138(2) Uani 1 2 d S T P . .
O1 O 0.2850(3) 0.5920(2) 0.71507(7) 0.0152(5) Uani 1 1 d . . . . .
O2 O 0.5000 0.9259(4) 0.7500 0.0179(7) Uani 1 2 d S T P . .
H2A H 0.3990 0.9780 0.7436 0.021 Uiso 1 1 d R U . . .
N1 N 0.5944(3) 0.6947(3) 0.66978(9) 0.0133(5) Uani 1 1 d . . . . .
C10 C 0.4596(4) 0.6406(4) 0.63686(11) 0.0141(6) Uani 1 1 d . . . . .
C9 C 0.2975(4) 0.5851(3) 0.66218(10) 0.0142(6) Uani 1 1 d . . . . .
C8 C 0.1606(4) 0.5260(4) 0.62977(11) 0.0182(7) Uani 1 1 d . . . . .
H8 H 0.0534 0.4878 0.6450 0.022 Uiso 1 1 calc R U . . .
C2 C 0.7485(4) 0.7493(4) 0.64949(11) 0.0159(6) Uani 1 1 d . . . . .
C6 C 0.3366(5) 0.5784(4) 0.54939(11) 0.0192(7) Uani 1 1 d . . . . .
H6 H 0.3464 0.5764 0.5123 0.023 Uiso 1 1 calc R U . . .
C1 C 0.8916(4) 0.8063(4) 0.68716(13) 0.0208(7) Uani 1 1 d . . . . .
H1A H 0.8568 0.9030 0.6992 0.031 Uiso 1 1 calc R U . . .
H1B H 1.0089 0.8115 0.6692 0.031 Uiso 1 1 calc R U . . .
H1C H 0.9012 0.7411 0.7173 0.031 Uiso 1 1 calc R U . . .
C3 C 0.7769(4) 0.7529(4) 0.59333(11) 0.0196(7) Uani 1 1 d . . . . .
H3 H 0.8853 0.7927 0.5794 0.023 Uiso 1 1 calc R U . . .
C5 C 0.4802(4) 0.6383(4) 0.58060(11) 0.0164(7) Uani 1 1 d . . . . .
C4 C 0.6459(5) 0.6983(4) 0.56013(12) 0.0217(7) Uani 1 1 d . . . . .
H4 H 0.6653 0.7003 0.5234 0.026 Uiso 1 1 calc R U . . .
C7 C 0.1828(5) 0.5233(4) 0.57393(11) 0.0210(7) Uani 1 1 d . . . . .
H7 H 0.0894 0.4826 0.5530 0.025 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 O1 2.015(2) . ?
Zn1 O1 2.015(2) 3_656 ?
Zn1 O2 2.087(3) . ?
Zn1 N1 2.120(3) . ?
Zn1 N1 2.120(3) 3_656 ?
O1 C9 1.328(3) . ?
O2 H2A 0.8839 . ?
N1 C2 1.320(4) . ?
N1 C10 1.367(4) . ?
C10 C5 1.416(4) . ?
C10 C9 1.423(4) . ?
C9 C8 1.387(4) . ?
C8 C7 1.407(4) . ?
C8 H8 0.9300 . ?
C2 C3 1.421(4) . ?
C2 C1 1.491(4) . ?
C6 C7 1.364(5) . ?
C6 C5 1.408(4) . ?
C6 H6 0.9300 . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C3 C4 1.353(5) . ?
C3 H3 0.9300 . ?
C5 C4 1.411(4) . ?
C4 H4 0.9300 . ?
C7 H7 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Zn1 O1 124.48(13) . 3_656 ?
O1 Zn1 O2 117.76(6) . . ?
O1 Zn1 O2 117.76(6) 3_656 . ?
O1 Zn1 N1 80.54(9) . . ?
O1 Zn1 N1 99.27(9) 3_656 . ?
O2 Zn1 N1 90.20(7) . . ?
O1 Zn1 N1 99.27(9) . 3_656 ?
O1 Zn1 N1 80.54(9) 3_656 3_656 ?
O2 Zn1 N1 90.20(6) . 3_656 ?
N1 Zn1 N1 179.60(13) . 3_656 ?
C9 O1 Zn1 113.68(18) . . ?
Zn1 O2 H2A 122.3 . . ?
C2 N1 C10 120.2(3) . . ?
C2 N1 Zn1 129.4(2) . . ?
C10 N1 Zn1 110.04(19) . . ?
N1 C10 C5 122.0(3) . . ?
N1 C10 C9 116.4(2) . . ?
C5 C10 C9 121.6(3) . . ?
O1 C9 C8 123.5(3) . . ?
O1 C9 C10 118.9(3) . . ?
C8 C9 C10 117.6(2) . . ?
C9 C8 C7 120.4(3) . . ?
C9 C8 H8 119.8 . . ?
C7 C8 H8 119.8 . . ?
N1 C2 C3 120.7(3) . . ?
N1 C2 C1 118.1(3) . . ?
C3 C2 C1 121.2(3) . . ?
C7 C6 C5 119.5(3) . . ?
C7 C6 H6 120.3 . . ?
C5 C6 H6 120.3 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C4 C3 C2 119.9(3) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
C6 C5 C4 124.9(3) . . ?
C6 C5 C10 118.7(3) . . ?
C4 C5 C10 116.4(3) . . ?
C3 C4 C5 120.8(3) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 H4 119.6 . . ?
C6 C7 C8 122.3(3) . . ?
C6 C7 H7 118.9 . . ?
C8 C7 H7 118.9 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C1 H1C O1 0.96 2.55 3.374(4) 144.0 3_656
O2 H2A O1 0.88 1.83 2.696(3) 166.6 8_665

_refine_diff_density_max         1.054
_refine_diff_density_min         -1.478
_refine_diff_density_rms         0.132

####################################################################### 
# 
# 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_S
_database_code_depnum_ccdc_archive 'CCDC 1915925'
loop_
_audit_author_name
_audit_author_address
Zn
;The Cambridge Crystallographic Data Cemtre
China
;
_audit_update_record             
;
2019-05-14 deposited with the CCDC.	2020-01-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H18 N2 O3 Zn'
_chemical_formula_weight         399.73

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

_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_H-M_alt        'P b c n'
_space_group_name_Hall           '-P 2n 2ab'

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

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

_cell_length_a                   7.2405(12)
_cell_length_b                   9.0605(13)
_cell_length_c                   25.074(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1644.9(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3357
_cell_measurement_theta_min      3.25
_cell_measurement_theta_max      27.15

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.614
_exptl_crystal_F_000             824
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    1.517
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(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            12053
_diffrn_reflns_av_unetI/netI     0.0470
_diffrn_reflns_av_R_equivalents  0.0744
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         3.249
_diffrn_reflns_theta_max         27.598
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             1903
_reflns_number_gt                1441
_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    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_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)+(0.0435P)²+4.6173P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1903
_refine_ls_number_parameters     124
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0742
_refine_ls_R_factor_gt           0.0509
_refine_ls_wR_factor_ref         0.1205
_refine_ls_wR_factor_gt          0.1108
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_restrained_S_all      1.086
_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 0.500000 0.30426(6) 0.250000 0.01456(18) Uani 1 2 d S T P . .
O1 O 0.7152(3) 0.4076(3) 0.28507(9) 0.0145(5) Uani 1 1 d . . . . .
O2 O 0.500000 0.0734(4) 0.250000 0.0225(8) Uani 1 2 d DS T P . .
N1 N 0.4061(4) 0.3048(3) 0.33001(11) 0.0141(6) Uani 1 1 d . . . . .
C9 C 0.7033(5) 0.4144(4) 0.33785(13) 0.0145(7) Uani 1 1 d . . . . .
C2 C 0.2506(5) 0.2509(4) 0.35046(13) 0.0159(7) Uani 1 1 d . . . . .
C10 C 0.5396(5) 0.3589(4) 0.36293(14) 0.0147(7) Uani 1 1 d . . . . .
C8 C 0.8392(5) 0.4738(4) 0.37030(14) 0.0188(7) Uani 1 1 d . . . . .
H8 H 0.946162 0.511977 0.355078 0.023 Uiso 1 1 calc R U . . .
C3 C 0.2232(5) 0.2472(4) 0.40655(14) 0.0212(8) Uani 1 1 d . . . . .
H3 H 0.114995 0.207392 0.420458 0.025 Uiso 1 1 calc R U . . .
C5 C 0.5195(5) 0.3611(4) 0.41929(14) 0.0178(7) Uani 1 1 d . . . . .
C1 C 0.1090(5) 0.1935(4) 0.31275(15) 0.0207(8) Uani 1 1 d . . . . .
H1A H 0.096579 0.260359 0.283262 0.031 Uiso 1 1 calc R U . . .
H1B H -0.007406 0.184841 0.330830 0.031 Uiso 1 1 calc R U . . .
H1C H 0.146393 0.098354 0.299848 0.031 Uiso 1 1 calc R U . . .
C4 C 0.3542(5) 0.3015(4) 0.43993(14) 0.0213(8) Uani 1 1 d . . . . .
H4 H 0.335011 0.299318 0.476599 0.026 Uiso 1 1 calc R U . . .
C6 C 0.6635(5) 0.4220(4) 0.45078(14) 0.0194(8) Uani 1 1 d . . . . .
H6 H 0.653380 0.424411 0.487745 0.023 Uiso 1 1 calc R U . . .
C7 C 0.8170(5) 0.4769(4) 0.42623(14) 0.0216(8) Uani 1 1 d . . . . .
H7 H 0.910193 0.517850 0.447045 0.026 Uiso 1 1 calc R U . . .
H2 H 0.595(5) 0.032(5) 0.263(2) 0.062(18) Uiso 1 1 d D . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Zn1 O1 2.019(2) . ?
Zn1 O1 2.019(2) 3_655 ?
Zn1 O2 2.092(4) . ?
Zn1 N1 2.118(3) 3_655 ?
Zn1 N1 2.118(3) . ?
O1 C9 1.328(4) . ?
O2 H2 0.853(10) . ?
O2 H2 0.853(10) 3_655 ?
N1 C2 1.330(4) . ?
N1 C10 1.362(4) . ?
C9 C8 1.386(5) . ?
C9 C10 1.433(5) . ?
C2 C3 1.421(5) . ?
C2 C1 1.488(5) . ?
C10 C5 1.421(5) . ?
C8 C7 1.412(5) . ?
C8 H8 0.9300 . ?
C3 C4 1.358(5) . ?
C3 H3 0.9300 . ?
C5 C4 1.411(5) . ?
C5 C6 1.420(5) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C4 H4 0.9300 . ?
C6 C7 1.365(5) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Zn1 O1 124.72(14) . 3_655 ?
O1 Zn1 O2 117.64(7) . . ?
O1 Zn1 O2 117.64(7) 3_655 . ?
O1 Zn1 N1 99.43(10) . 3_655 ?
O1 Zn1 N1 80.46(10) 3_655 3_655 ?
O2 Zn1 N1 90.12(8) . 3_655 ?
O1 Zn1 N1 80.46(10) . . ?
O1 Zn1 N1 99.43(10) 3_655 . ?
O2 Zn1 N1 90.12(8) . . ?
N1 Zn1 N1 179.76(15) 3_655 . ?
C9 O1 Zn1 113.9(2) . . ?
Zn1 O2 H2 116(4) . . ?
Zn1 O2 H2 116(4) . 3_655 ?
H2 O2 H2 128(7) . 3_655 ?
C2 N1 C10 119.9(3) . . ?
C2 N1 Zn1 129.5(2) . . ?
C10 N1 Zn1 110.3(2) . . ?
O1 C9 C8 123.9(3) . . ?
O1 C9 C10 118.3(3) . . ?
C8 C9 C10 117.8(3) . . ?
N1 C2 C3 120.6(3) . . ?
N1 C2 C1 117.8(3) . . ?
C3 C2 C1 121.6(3) . . ?
N1 C10 C5 122.4(3) . . ?
N1 C10 C9 116.6(3) . . ?
C5 C10 C9 121.1(3) . . ?
C9 C8 C7 120.7(3) . . ?
C9 C8 H8 119.7 . . ?
C7 C8 H8 119.7 . . ?
C4 C3 C2 120.3(3) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C4 C5 C6 124.6(3) . . ?
C4 C5 C10 116.5(3) . . ?
C6 C5 C10 118.9(3) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C3 C4 C5 120.3(3) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C7 C6 C5 119.3(3) . . ?
C7 C6 H6 120.4 . . ?
C5 C6 H6 120.4 . . ?
C6 C7 C8 122.2(3) . . ?
C6 C7 H7 118.9 . . ?
C8 C7 H7 118.9 . . ?

_refine_diff_density_max         0.531
_refine_diff_density_min         -0.590
_refine_diff_density_rms         0.096

