# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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_cpd2
_database_code_depnum_ccdc_archive 'CCDC 2142350'
loop_
_audit_author_name
_audit_author_address
'Dr Sreejith S S'
;Cochin University of Science and Technology, Kerala
India
;
_audit_update_record             
;
2022-01-16 deposited with the CCDC.	2022-05-27 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT029_cpd2                
;
PROBLEM: diffrn_measured_fraction_theta_full value Low . 0.877 Why?
RESPONSE: Crystal quality was not optimal; we repeated the experiments under 
different conditions but in vain. A low temperature acquistion may improve 
the quality but currently it is unavailable.

;
_vrf_PLAT911_cpd2                
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L= 0.600 222 Report
RESPONSE: These reflections were probably affected by unexpected deviations
in their intensities for symmetry equivalent measurements and omitted during
initial data reduction.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H 18 Br2 Cu N2 O5'
_chemical_formula_sum            'C18 H18 Br2 Cu N2 O5'
_chemical_formula_weight         565.70

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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           62
_space_group_name_H-M_alt        'P n m a'
_space_group_name_Hall           '-P 2ac 2n'

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

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

_cell_length_a                   8.7406(8)
_cell_length_b                   28.034(5)
_cell_length_c                   8.0013(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1960.6(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2007
_cell_measurement_theta_min      2.64
_cell_measurement_theta_max      28.13

_exptl_crystal_description       Block
_exptl_crystal_colour            Green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.917
_exptl_crystal_F_000             1116
_exptl_transmission_factor_min   0.317
_exptl_transmission_factor_max   0.330
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.220
_exptl_absorpt_coefficient_mu    5.223
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   'SADABS (Bruker, 2004)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker axs kappa apex2 CCD Diffractometer'
_diffrn_measurement_method       'ω and φ scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7665
_diffrn_reflns_av_unetI/netI     0.0885
_diffrn_reflns_av_R_equivalents  0.0797
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         2.647
_diffrn_reflns_theta_max         28.139
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.819
_diffrn_measured_fraction_theta_full 0.877
_diffrn_reflns_Laue_measured_fraction_max 0.819
_diffrn_reflns_Laue_measured_fraction_full 0.877
_diffrn_reflns_point_group_measured_fraction_max 0.819
_diffrn_reflns_point_group_measured_fraction_full 0.877
_reflns_number_total             2007
_reflns_number_gt                1110
_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)+(0.0331P)²+5.2444P] 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         2007
_refine_ls_number_parameters     143
_refine_ls_number_restraints     14
_refine_ls_R_factor_all          0.1305
_refine_ls_R_factor_gt           0.0531
_refine_ls_wR_factor_ref         0.1199
_refine_ls_wR_factor_gt          0.0996
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.024
_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
Br1 Br 0.29146(10) -0.00696(3) 0.64447(12) 0.0775(4) Uani 1 1 d . . . . .
Cu1 Cu 0.43621(10) 0.2500 0.48217(13) 0.0320(3) Uani 1 2 d S T P A .
O1 O 0.2831(4) 0.20077(14) 0.4534(5) 0.0351(10) Uani 1 1 d . . . . .
O2 O 0.0390(4) 0.14974(14) 0.4086(5) 0.0447(12) Uani 1 1 d . . . . .
O5 O 0.5243(6) 0.2500 0.2103(8) 0.0442(17) Uani 1 2 d DS T P . .
H5A H 0.562(6) 0.2260(4) 0.168(6) 0.066 Uiso 1 1 d D U . . .
N1 N 0.5850(5) 0.2042(2) 0.5669(7) 0.0465(14) Uani 1 1 d . U . . .
C1 C -0.0948(6) 0.1228(3) 0.3803(8) 0.053(2) Uani 1 1 d . . . . .
H1A H -0.1741 0.1434 0.3388 0.079 Uiso 1 1 calc R U . . .
H1B H -0.1275 0.1085 0.4831 0.079 Uiso 1 1 calc R U . . .
H1C H -0.0739 0.0983 0.2996 0.079 Uiso 1 1 calc R U . . .
C2 C 0.1610(6) 0.1265(2) 0.4764(7) 0.0328(15) Uani 1 1 d . . . . .
C3 C 0.1623(6) 0.0792(2) 0.5158(8) 0.0404(16) Uani 1 1 d . . . . .
H3 H 0.0760 0.0605 0.4975 0.048 Uiso 1 1 calc R U . . .
C4 C 0.2945(7) 0.0590(2) 0.5840(8) 0.0410(16) Uani 1 1 d . . . . .
C5 C 0.4217(7) 0.0857(2) 0.6111(8) 0.0423(17) Uani 1 1 d . . . . .
H5 H 0.5082 0.0717 0.6574 0.051 Uiso 1 1 calc R U . . .
C6 C 0.4236(6) 0.1342(2) 0.5700(7) 0.0310(15) Uani 1 1 d . . . . .
C7 C 0.2926(5) 0.1561(2) 0.4990(7) 0.0321(15) Uani 1 1 d . . . . .
C8 C 0.5620(6) 0.1600(3) 0.5999(8) 0.0436(17) Uani 1 1 d . . . . .
H8 H 0.6427 0.1432 0.6477 0.052 Uiso 1 1 calc R U . . .
C9 C 0.7430(19) 0.2230(6) 0.563(2) 0.046(4) Uani 0.5 1 d . U P A -1
H9A H 0.7793 0.2274 0.4490 0.055 Uiso 0.5 1 calc R U P A -1
H9B H 0.8136 0.2027 0.6232 0.055 Uiso 0.5 1 calc R U P A -1
C10 C 0.7181(19) 0.2697(5) 0.6497(19) 0.048(4) Uani 0.5 1 d . U P A -1
H10A H 0.8101 0.2890 0.6428 0.057 Uiso 0.5 1 calc R U P A -1
H10B H 0.6954 0.2642 0.7668 0.057 Uiso 0.5 1 calc R U P A -1


_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
Br1 C4 1.913(6) . ?
Cu1 O1 1.936(4) . ?
Cu1 O1 1.936(4) 8_565 ?
Cu1 N1 1.950(5) 8_565 ?
Cu1 N1 1.950(5) . ?
Cu1 O5 2.308(6) . ?
O1 C7 1.306(7) . ?
O2 C2 1.362(6) . ?
O2 C1 1.410(6) . ?
O5 H5A 0.821(18) . ?
N1 C8 1.282(8) . ?
N1 C9 1.479(17) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C3 1.364(8) . ?
C2 C7 1.430(7) . ?
C3 C4 1.397(8) . ?
C3 H3 0.9300 . ?
C4 C5 1.357(8) . ?
C5 C6 1.398(8) . ?
C5 H5 0.9300 . ?
C6 C7 1.418(7) . ?
C6 C8 1.430(8) . ?
C8 H8 0.9300 . ?
C9 C10 1.501(17) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 N1 1.527(16) 8_565 ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Cu1 O1 90.9(2) . 8_565 ?
O1 Cu1 N1 166.4(2) . 8_565 ?
O1 Cu1 N1 91.85(19) 8_565 8_565 ?
O1 Cu1 N1 91.85(19) . . ?
O1 Cu1 N1 166.4(2) 8_565 . ?
N1 Cu1 N1 82.5(3) 8_565 . ?
O1 Cu1 O5 96.81(16) . . ?
O1 Cu1 O5 96.81(16) 8_565 . ?
N1 Cu1 O5 96.0(2) 8_565 . ?
N1 Cu1 O5 96.0(2) . . ?
C7 O1 Cu1 127.3(3) . . ?
C2 O2 C1 117.2(5) . . ?
Cu1 O5 H5A 121(3) . . ?
C8 N1 C9 119.7(7) . . ?
C8 N1 Cu1 127.1(4) . . ?
C9 N1 Cu1 112.3(7) . . ?
O2 C1 H1A 109.5 . . ?
O2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O2 C2 C3 124.3(5) . . ?
O2 C2 C7 113.7(5) . . ?
C3 C2 C7 122.0(5) . . ?
C2 C3 C4 119.3(5) . . ?
C2 C3 H3 120.3 . . ?
C4 C3 H3 120.3 . . ?
C5 C4 C3 121.2(6) . . ?
C5 C4 Br1 120.3(5) . . ?
C3 C4 Br1 118.6(5) . . ?
C4 C5 C6 120.5(6) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C5 C6 C7 120.4(5) . . ?
C5 C6 C8 117.5(5) . . ?
C7 C6 C8 122.0(5) . . ?
O1 C7 C6 125.4(5) . . ?
O1 C7 C2 118.0(5) . . ?
C6 C7 C2 116.6(5) . . ?
N1 C8 C6 125.9(5) . . ?
N1 C8 H8 117.0 . . ?
C6 C8 H8 117.0 . . ?
N1 C9 C10 99.5(13) . . ?
N1 C9 H9A 111.9 . . ?
C10 C9 H9A 111.9 . . ?
N1 C9 H9B 111.9 . . ?
C10 C9 H9B 111.9 . . ?
H9A C9 H9B 109.6 . . ?
C9 C10 N1 109.1(14) . 8_565 ?
C9 C10 H10A 109.9 . . ?
N1 C10 H10A 109.9 8_565 . ?
C9 C10 H10B 109.9 . . ?
N1 C10 H10B 109.9 8_565 . ?
H10A C10 H10B 108.3 . . ?

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
C1 O2 C2 C3 0.9(9) . . . . ?
C1 O2 C2 C7 179.2(5) . . . . ?
O2 C2 C3 C4 179.7(5) . . . . ?
C7 C2 C3 C4 1.5(9) . . . . ?
C2 C3 C4 C5 -0.2(10) . . . . ?
C2 C3 C4 Br1 178.2(5) . . . . ?
C3 C4 C5 C6 -0.5(10) . . . . ?
Br1 C4 C5 C6 -178.8(5) . . . . ?
C4 C5 C6 C7 -0.1(9) . . . . ?
C4 C5 C6 C8 -179.2(6) . . . . ?
Cu1 O1 C7 C6 -4.4(8) . . . . ?
Cu1 O1 C7 C2 175.6(4) . . . . ?
C5 C6 C7 O1 -178.7(6) . . . . ?
C8 C6 C7 O1 0.3(9) . . . . ?
C5 C6 C7 C2 1.3(9) . . . . ?
C8 C6 C7 C2 -179.6(6) . . . . ?
O2 C2 C7 O1 -0.3(8) . . . . ?
C3 C2 C7 O1 178.0(6) . . . . ?
O2 C2 C7 C6 179.7(5) . . . . ?
C3 C2 C7 C6 -2.0(9) . . . . ?
C9 N1 C8 C6 -164.0(9) . . . . ?
Cu1 N1 C8 C6 4.7(10) . . . . ?
C5 C6 C8 N1 178.6(7) . . . . ?
C7 C6 C8 N1 -0.5(10) . . . . ?
C8 N1 C9 C10 -138.6(10) . . . . ?
Cu1 N1 C9 C10 51.1(11) . . . . ?
N1 C9 C10 N1 -51.1(11) . . . 8_565 ?

_refine_diff_density_max         0.556
_refine_diff_density_min         -0.721
_refine_diff_density_rms         0.109


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: DMSO'
####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1915472'
loop_
_audit_author_name
_audit_author_address
'Dr Sreejith S S'
;Cochin University of Science and Technology, Kerala
India
;
_audit_update_record             
;
2022-01-16 deposited with the CCDC.	2022-05-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H24 Br2 Cu N2 O5'
_chemical_formula_weight         607.78

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   12.8088(10)
_cell_length_b                   12.5718(9)
_cell_length_c                   14.2153(10)
_cell_angle_alpha                90
_cell_angle_beta                 99.738(4)
_cell_angle_gamma                90
_cell_volume                     2256.1(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5665
_cell_measurement_theta_min      2.559
_cell_measurement_theta_max      28.411

_exptl_crystal_description       Block
_exptl_crystal_colour            Green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.789
_exptl_crystal_F_000             1212
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.450
_exptl_crystal_size_min          0.400
_exptl_absorpt_coefficient_mu    4.546
_shelx_estimated_absorpt_T_min   0.210
_shelx_estimated_absorpt_T_max   0.264
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.118
_exptl_absorpt_correction_T_max  0.162
_exptl_absorpt_process_details   'SADABS (Bruker, 2004)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker axs kappa apex2 CCD Diffractometer'
_diffrn_measurement_method       'ω and φ scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            34915
_diffrn_reflns_av_unetI/netI     0.0330
_diffrn_reflns_av_R_equivalents  0.0355
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.559
_diffrn_reflns_theta_max         28.411
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             5598
_reflns_number_gt                4120
_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       'APEX2 (Bruker, 2004)'
_computing_cell_refinement       'APEX2/SAINT (Bruker, 2004)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2004)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'ORTEP3 (Farrugia, 1997)'
_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)+(0.0962P)²+3.0772P] 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         5598
_refine_ls_number_parameters     288
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0626
_refine_ls_R_factor_gt           0.0376
_refine_ls_wR_factor_ref         0.1245
_refine_ls_wR_factor_gt          0.1061
_refine_ls_goodness_of_fit_ref   0.804
_refine_ls_restrained_S_all      0.804
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br2 Br 0.02804(3) 0.87463(3) 0.08186(3) 0.04913(14) Uani 1 1 d . . . . .
Cu1 Cu 0.40507(3) 0.42438(3) 0.11823(3) 0.02641(12) Uani 1 1 d . . . . .
Br1 Br 0.84897(4) 0.05284(4) 0.16554(4) 0.06345(17) Uani 1 1 d . . . . .
O1 O 0.39754(17) 0.57723(17) 0.09950(17) 0.0309(5) Uani 1 1 d . . . . .
O3 O 0.55829(18) 0.43098(18) 0.14666(18) 0.0325(5) Uani 1 1 d . . . . .
O4 O 0.7587(2) 0.4609(2) 0.13764(19) 0.0400(6) Uani 1 1 d . . . . .
O2 O 0.42996(19) 0.77944(18) 0.08988(19) 0.0379(6) Uani 1 1 d . . . . .
C18 C 0.1420(3) 0.7777(3) 0.0855(2) 0.0309(7) Uani 1 1 d . . . . .
N2 N 0.2499(2) 0.4115(2) 0.08830(19) 0.0276(6) Uani 1 1 d . . . . .
C9 C 0.2174(3) 0.2337(3) 0.1575(3) 0.0384(8) Uani 1 1 d . . . . .
C19 C 0.1239(3) 0.6715(3) 0.0851(2) 0.0299(7) Uani 1 1 d . . . . .
H19 H 0.055315 0.645867 0.082316 0.036 Uiso 1 1 calc R U . . .
C14 C 0.2091(3) 0.6000(2) 0.0890(2) 0.0267(6) Uani 1 1 d . . . . .
C15 C 0.3140(2) 0.6366(2) 0.0934(2) 0.0240(6) Uani 1 1 d . . . . .
C13 C 0.1832(2) 0.4883(3) 0.0820(2) 0.0287(7) Uani 1 1 d . . . . .
H13 H 0.111781 0.470413 0.072092 0.034 Uiso 1 1 calc R U . . .
C12 C 0.2107(3) 0.3033(3) 0.0676(3) 0.0359(8) Uani 1 1 d . . . . .
H12A H 0.251541 0.270035 0.024072 0.043 Uiso 1 1 calc R U . . .
H12B H 0.137523 0.306612 0.035910 0.043 Uiso 1 1 calc R U . . .
C8 C 0.3132(3) 0.2665(3) 0.2329(3) 0.0373(8) Uani 1 1 d . . . . .
H8A H 0.294663 0.328696 0.266837 0.045 Uiso 1 1 calc R U . . .
H8B H 0.329915 0.209310 0.278787 0.045 Uiso 1 1 calc R U . . .
N1 N 0.4067(2) 0.2903(2) 0.19020(19) 0.0310(6) Uani 1 1 d . . . . .
C7 C 0.4841(3) 0.2243(3) 0.2018(2) 0.0316(7) Uani 1 1 d . . . . .
H7 H 0.474400 0.159669 0.230899 0.038 Uiso 1 1 calc R U . . .
C1 C 0.5847(3) 0.2430(3) 0.1731(2) 0.0305(7) Uani 1 1 d . . . . .
C6 C 0.6182(2) 0.3470(3) 0.1543(2) 0.0278(6) Uani 1 1 d . . . . .
C5 C 0.7279(3) 0.3586(3) 0.1479(2) 0.0303(7) Uani 1 1 d . . . . .
C20 C 0.8691(3) 0.4821(4) 0.1502(3) 0.0468(9) Uani 1 1 d . . . . .
H20A H 0.880160 0.556648 0.141053 0.070 Uiso 1 1 calc R U . . .
H20B H 0.901607 0.461938 0.213483 0.070 Uiso 1 1 calc R U . . .
H20C H 0.900010 0.442029 0.104383 0.070 Uiso 1 1 calc R U . . .
C4 C 0.7949(3) 0.2721(3) 0.1524(2) 0.0367(8) Uani 1 1 d . . . . .
H4 H 0.865667 0.281461 0.147029 0.044 Uiso 1 1 calc R U . . .
C3 C 0.7561(3) 0.1712(3) 0.1649(2) 0.0372(8) Uani 1 1 d . . . . .
C2 C 0.6551(3) 0.1555(3) 0.1782(2) 0.0359(8) Uani 1 1 d . . . . .
H2 H 0.631962 0.087571 0.190509 0.043 Uiso 1 1 calc R U . . .
C16 C 0.3270(3) 0.7497(2) 0.0898(2) 0.0270(6) Uani 1 1 d . . . . .
C21 C 0.4525(4) 0.8895(3) 0.0884(4) 0.0514(10) Uani 1 1 d . . . . .
H21A H 0.526796 0.899503 0.088616 0.077 Uiso 1 1 calc R U . . .
H21B H 0.412788 0.920733 0.031765 0.077 Uiso 1 1 calc R U . . .
H21C H 0.433043 0.922824 0.143640 0.077 Uiso 1 1 calc R U . . .
C17 C 0.2439(3) 0.8189(3) 0.0874(2) 0.0305(7) Uani 1 1 d . . . . .
H17 H 0.255019 0.892030 0.086990 0.037 Uiso 1 1 calc R U . . .
C10 C 0.2277(4) 0.1179(3) 0.1292(4) 0.0574(12) Uani 1 1 d . . . . .
H10A H 0.167661 0.098364 0.082296 0.086 Uiso 1 1 calc R U . . .
H10B H 0.291389 0.108807 0.102891 0.086 Uiso 1 1 calc R U . . .
H10C H 0.230422 0.073363 0.184417 0.086 Uiso 1 1 calc R U . . .
C11 C 0.1176(4) 0.2490(4) 0.2033(4) 0.0646(13) Uani 1 1 d . . . . .
H11A H 0.112040 0.322256 0.220895 0.097 Uiso 1 1 calc R U . . .
H11B H 0.056049 0.229168 0.158400 0.097 Uiso 1 1 calc R U . . .
H11C H 0.122610 0.205139 0.259187 0.097 Uiso 1 1 calc R U . . .
O1W O 0.4043(2) 0.3765(2) -0.04151(19) 0.0383(6) Uani 1 1 d D . . . .
H2W H 0.4657(17) 0.356(3) -0.047(3) 0.061(14) Uiso 1 1 d D . . . .
H1W H 0.389(3) 0.429(2) -0.079(3) 0.054(14) 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
Br2 C18 1.895(3) . ?
Cu1 O3 1.937(2) . ?
Cu1 O1 1.940(2) . ?
Cu1 N2 1.967(3) . ?
Cu1 N1 1.970(3) . ?
Cu1 O1W 2.348(3) . ?
Br1 C3 1.904(3) . ?
O1 C15 1.296(4) . ?
O3 C6 1.299(4) . ?
O4 C5 1.360(4) . ?
O4 C20 1.420(4) . ?
O2 C16 1.371(4) . ?
O2 C21 1.414(4) . ?
C18 C19 1.355(5) . ?
C18 C17 1.401(5) . ?
N2 C13 1.282(4) . ?
N2 C12 1.464(4) . ?
C9 C10 1.522(5) . ?
C9 C8 1.542(5) . ?
C9 C12 1.539(5) . ?
C9 C11 1.542(5) . ?
C19 C14 1.408(4) . ?
C19 H19 0.9300 . ?
C14 C15 1.411(4) . ?
C14 C13 1.442(4) . ?
C15 C16 1.433(4) . ?
C13 H13 0.9300 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C8 N1 1.461(4) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
N1 C7 1.282(4) . ?
C7 C1 1.434(5) . ?
C7 H7 0.9300 . ?
C1 C6 1.416(5) . ?
C1 C2 1.416(5) . ?
C6 C5 1.431(5) . ?
C5 C4 1.380(5) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C4 C3 1.385(5) . ?
C4 H4 0.9300 . ?
C3 C2 1.354(5) . ?
C2 H2 0.9300 . ?
C16 C17 1.371(4) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C17 H17 0.9300 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
O1W H2W 0.846(10) . ?
O1W H1W 0.849(10) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O3 Cu1 O1 90.65(9) . . ?
O3 Cu1 N2 177.70(10) . . ?
O1 Cu1 N2 91.53(10) . . ?
O3 Cu1 N1 90.41(10) . . ?
O1 Cu1 N1 156.16(11) . . ?
N2 Cu1 N1 87.91(11) . . ?
O3 Cu1 O1W 92.92(10) . . ?
O1 Cu1 O1W 97.41(10) . . ?
N2 Cu1 O1W 86.05(10) . . ?
N1 Cu1 O1W 106.32(11) . . ?
C15 O1 Cu1 127.0(2) . . ?
C6 O3 Cu1 123.1(2) . . ?
C5 O4 C20 117.7(3) . . ?
C16 O2 C21 117.8(3) . . ?
C19 C18 C17 121.5(3) . . ?
C19 C18 Br2 120.2(3) . . ?
C17 C18 Br2 118.3(2) . . ?
C13 N2 C12 119.0(3) . . ?
C13 N2 Cu1 126.2(2) . . ?
C12 N2 Cu1 114.8(2) . . ?
C10 C9 C8 110.2(3) . . ?
C10 C9 C12 108.6(3) . . ?
C8 C9 C12 110.5(3) . . ?
C10 C9 C11 110.3(3) . . ?
C8 C9 C11 107.0(4) . . ?
C12 C9 C11 110.2(3) . . ?
C18 C19 C14 119.9(3) . . ?
C18 C19 H19 120.1 . . ?
C14 C19 H19 120.1 . . ?
C15 C14 C19 121.3(3) . . ?
C15 C14 C13 121.8(3) . . ?
C19 C14 C13 116.8(3) . . ?
O1 C15 C14 125.7(3) . . ?
O1 C15 C16 118.3(3) . . ?
C14 C15 C16 116.0(3) . . ?
N2 C13 C14 125.8(3) . . ?
N2 C13 H13 117.1 . . ?
C14 C13 H13 117.1 . . ?
N2 C12 C9 113.1(3) . . ?
N2 C12 H12A 109.0 . . ?
C9 C12 H12A 109.0 . . ?
N2 C12 H12B 109.0 . . ?
C9 C12 H12B 109.0 . . ?
H12A C12 H12B 107.8 . . ?
N1 C8 C9 112.2(3) . . ?
N1 C8 H8A 109.2 . . ?
C9 C8 H8A 109.2 . . ?
N1 C8 H8B 109.2 . . ?
C9 C8 H8B 109.2 . . ?
H8A C8 H8B 107.9 . . ?
C7 N1 C8 119.0(3) . . ?
C7 N1 Cu1 124.1(2) . . ?
C8 N1 Cu1 117.0(2) . . ?
N1 C7 C1 124.8(3) . . ?
N1 C7 H7 117.6 . . ?
C1 C7 H7 117.6 . . ?
C6 C1 C2 121.0(3) . . ?
C6 C1 C7 121.4(3) . . ?
C2 C1 C7 117.0(3) . . ?
O3 C6 C1 124.9(3) . . ?
O3 C6 C5 119.0(3) . . ?
C1 C6 C5 116.0(3) . . ?
O4 C5 C4 124.1(3) . . ?
O4 C5 C6 114.1(3) . . ?
C4 C5 C6 121.7(3) . . ?
O4 C20 H20A 109.5 . . ?
O4 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
O4 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C5 C4 C3 119.6(3) . . ?
C5 C4 H4 120.2 . . ?
C3 C4 H4 120.2 . . ?
C2 C3 C4 121.6(3) . . ?
C2 C3 Br1 119.8(3) . . ?
C4 C3 Br1 118.6(3) . . ?
C3 C2 C1 119.7(3) . . ?
C3 C2 H2 120.1 . . ?
C1 C2 H2 120.1 . . ?
O2 C16 C17 124.7(3) . . ?
O2 C16 C15 112.8(3) . . ?
C17 C16 C15 122.5(3) . . ?
O2 C21 H21A 109.5 . . ?
O2 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
O2 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C16 C17 C18 118.8(3) . . ?
C16 C17 H17 120.6 . . ?
C18 C17 H17 120.6 . . ?
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 . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
Cu1 O1W H2W 109(3) . . ?
Cu1 O1W H1W 111(3) . . ?
H2W O1W H1W 108(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C17 C18 C19 C14 1.6(5) . . . . ?
Br2 C18 C19 C14 -179.2(2) . . . . ?
C18 C19 C14 C15 0.1(5) . . . . ?
C18 C19 C14 C13 -176.0(3) . . . . ?
Cu1 O1 C15 C14 -7.3(4) . . . . ?
Cu1 O1 C15 C16 173.4(2) . . . . ?
C19 C14 C15 O1 178.2(3) . . . . ?
C13 C14 C15 O1 -5.9(5) . . . . ?
C19 C14 C15 C16 -2.4(4) . . . . ?
C13 C14 C15 C16 173.5(3) . . . . ?
C12 N2 C13 C14 -172.3(3) . . . . ?
Cu1 N2 C13 C14 4.7(5) . . . . ?
C15 C14 C13 N2 7.1(5) . . . . ?
C19 C14 C13 N2 -176.8(3) . . . . ?
C13 N2 C12 C9 -107.2(4) . . . . ?
Cu1 N2 C12 C9 75.4(3) . . . . ?
C10 C9 C12 N2 -152.8(3) . . . . ?
C8 C9 C12 N2 -31.8(4) . . . . ?
C11 C9 C12 N2 86.3(4) . . . . ?
C10 C9 C8 N1 79.5(4) . . . . ?
C12 C9 C8 N1 -40.5(4) . . . . ?
C11 C9 C8 N1 -160.6(3) . . . . ?
C9 C8 N1 C7 -107.3(3) . . . . ?
C9 C8 N1 Cu1 73.1(3) . . . . ?
C8 N1 C7 C1 -172.8(3) . . . . ?
Cu1 N1 C7 C1 6.8(5) . . . . ?
N1 C7 C1 C6 18.5(5) . . . . ?
N1 C7 C1 C2 -170.7(3) . . . . ?
Cu1 O3 C6 C1 -20.9(4) . . . . ?
Cu1 O3 C6 C5 162.2(2) . . . . ?
C2 C1 C6 O3 178.6(3) . . . . ?
C7 C1 C6 O3 -10.9(5) . . . . ?
C2 C1 C6 C5 -4.4(5) . . . . ?
C7 C1 C6 C5 166.1(3) . . . . ?
C20 O4 C5 C4 -12.3(5) . . . . ?
C20 O4 C5 C6 167.5(3) . . . . ?
O3 C6 C5 O4 2.3(4) . . . . ?
C1 C6 C5 O4 -174.9(3) . . . . ?
O3 C6 C5 C4 -177.9(3) . . . . ?
C1 C6 C5 C4 4.9(5) . . . . ?
O4 C5 C4 C3 178.7(3) . . . . ?
C6 C5 C4 C3 -1.1(5) . . . . ?
C5 C4 C3 C2 -3.6(5) . . . . ?
C5 C4 C3 Br1 177.4(2) . . . . ?
C4 C3 C2 C1 4.1(5) . . . . ?
Br1 C3 C2 C1 -177.0(2) . . . . ?
C6 C1 C2 C3 0.1(5) . . . . ?
C7 C1 C2 C3 -170.8(3) . . . . ?
C21 O2 C16 C17 0.6(5) . . . . ?
C21 O2 C16 C15 -178.8(3) . . . . ?
O1 C15 C16 O2 2.2(4) . . . . ?
C14 C15 C16 O2 -177.1(3) . . . . ?
O1 C15 C16 C17 -177.2(3) . . . . ?
C14 C15 C16 C17 3.4(5) . . . . ?
O2 C16 C17 C18 178.7(3) . . . . ?
C15 C16 C17 C18 -2.0(5) . . . . ?
C19 C18 C17 C16 -0.6(5) . . . . ?
Br2 C18 C17 C16 -179.8(2) . . . . ?

_refine_diff_density_max         0.782
_refine_diff_density_min         -0.656
_refine_diff_density_rms         0.090


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: DMSO'
_exptl_crystal_preparation       'Potential anticancer activity'
####################################################################### 
# 
# 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_cpd4
_database_code_depnum_ccdc_archive 'CCDC 2142351'
loop_
_audit_author_name
_audit_author_address
'Dr S S Sreejith '
;Cochin University of Science and Technology, Kerala
India
;
_audit_update_record             
;
2022-01-16 deposited with the CCDC.	2022-05-27 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT306_cpd4                
;
PROBLEM: Isolated Oxygen Atom (H-atoms Missing ?) ....... O3S Check 
RESPONSE: The oxygen atom sits on 3-fold axis. Fixing hydrogen
atoms leads to symmetry generated unwanted extra hydrogen atoms
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H30 N2 O5 Zn, 1.5(H2 O), 0.5(O)'
_chemical_formula_sum            'C21 H27 Cu N2 O6'
_chemical_formula_weight         467

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

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

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

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

_cell_length_a                   23.6193(19)
_cell_length_b                   9.4893(6)
_cell_length_c                   20.9455(18)
_cell_angle_alpha                90
_cell_angle_beta                 112.966(8)
_cell_angle_gamma                90
_cell_volume                     4322.4(6)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5471
_cell_measurement_theta_min      2.715
_cell_measurement_theta_max      28.493

_exptl_crystal_description       Block
_exptl_crystal_colour            Green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.435
_exptl_crystal_F_000             1952
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    1.050
_shelx_estimated_absorpt_T_min   0.744
_shelx_estimated_absorpt_T_max   0.817
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.792
_exptl_absorpt_correction_T_max  0.825
_exptl_absorpt_process_details   'SADABS (Bruker, 2004)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker axs kappa apex2 CCD Diffractometer'
_diffrn_measurement_method       'ω and φ scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17280
_diffrn_reflns_av_unetI/netI     0.0341
_diffrn_reflns_av_R_equivalents  0.0292
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         2.715
_diffrn_reflns_theta_max         28.493
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             5471
_reflns_number_gt                4134
_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       'APEX2 (Bruker, 2004)'
_computing_cell_refinement       'APEX2/SAINT (Bruker, 2004)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2004)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'ORTEP3 (Farrugia, 1997)'
_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)+(0.0565P)²+1.4485P] 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         5471
_refine_ls_number_parameters     284
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0529
_refine_ls_R_factor_gt           0.0346
_refine_ls_wR_factor_ref         0.1028
_refine_ls_wR_factor_gt          0.0925
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.031
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.23387(2) 0.52865(2) 1.01581(2) 0.03240(9) Uani 1 1 d . . . . .
O1S O 0.07006(11) 0.4667(3) 0.86646(15) 0.0794(8) Uani 1 1 d . . . . .
O1 O 0.03830(7) 0.6276(2) 0.96711(10) 0.0707(6) Uani 1 1 d . . . . .
O4 O 0.15427(8) 0.45175(17) 0.78915(8) 0.0533(4) Uani 1 1 d . . . . .
N2 N 0.30677(7) 0.41182(18) 1.04359(8) 0.0347(4) Uani 1 1 d . . . . .
C13 C 0.32075(9) 0.3297(2) 1.00317(11) 0.0383(5) Uani 1 1 d . . . . .
H13 H 0.354571 0.270997 1.023710 0.046 Uiso 1 1 calc R U . . .
C14 C 0.28909(9) 0.3200(2) 0.92944(11) 0.0362(4) Uani 1 1 d . . . . .
C16 C 0.20761(10) 0.3794(2) 0.82039(11) 0.0391(4) Uani 1 1 d . . . . .
C21 C 0.11822(13) 0.4224(3) 0.71880(14) 0.0693(7) Uani 1 1 d . . . . .
H21A H 0.082075 0.480421 0.703332 0.104 Uiso 1 1 calc R U . . .
H21B H 0.141706 0.441786 0.691330 0.104 Uiso 1 1 calc R U . . .
H21C H 0.106391 0.324899 0.713911 0.104 Uiso 1 1 calc R U . . .
C15 C 0.23305(9) 0.39040(19) 0.89357(10) 0.0330(4) Uani 1 1 d . . . . .
C17 C 0.23560(11) 0.3028(3) 0.78576(13) 0.0520(6) Uani 1 1 d . . . . .
H17 H 0.218228 0.298645 0.737590 0.062 Uiso 1 1 calc R U . . .
C18 C 0.28955(12) 0.2316(3) 0.82202(15) 0.0627(7) Uani 1 1 d . . . . .
H18 H 0.308339 0.179190 0.798243 0.075 Uiso 1 1 calc R U . . .
C19 C 0.31528(11) 0.2378(3) 0.89225(14) 0.0527(6) Uani 1 1 d . . . . .
H19 H 0.350897 0.186790 0.916223 0.063 Uiso 1 1 calc R U . . .
C12 C 0.34201(9) 0.4076(2) 1.11805(11) 0.0392(5) Uani 1 1 d . . . . .
H12A H 0.371135 0.330336 1.128611 0.047 Uiso 1 1 calc R U . . .
H12B H 0.314272 0.388845 1.141101 0.047 Uiso 1 1 calc R U . . .
C9 C 0.37726(9) 0.5449(2) 1.14721(11) 0.0411(5) Uani 1 1 d . . . . .
C8 C 0.34044(9) 0.6752(2) 1.11074(12) 0.0422(5) Uani 1 1 d . . . . .
H8A H 0.354752 0.755301 1.141675 0.051 Uiso 1 1 calc R U . . .
H8B H 0.349160 0.694563 1.070015 0.051 Uiso 1 1 calc R U . . .
N1 N 0.27393(7) 0.66352(17) 1.08938(8) 0.0347(4) Uani 1 1 d . . . . .
C7 C 0.24590(10) 0.7522(2) 1.11264(10) 0.0361(4) Uani 1 1 d . . . . .
H7 H 0.270307 0.813813 1.146855 0.043 Uiso 1 1 calc R U . . .
C1 C 0.18065(9) 0.7664(2) 1.09129(10) 0.0359(4) Uani 1 1 d . . . . .
C2 C 0.15869(11) 0.8744(2) 1.12187(12) 0.0463(5) Uani 1 1 d . . . . .
H2 H 0.186574 0.930156 1.156418 0.056 Uiso 1 1 calc R U . . .
C3 C 0.09775(13) 0.8983(3) 1.10174(14) 0.0557(6) Uani 1 1 d . . . . .
H3 H 0.084079 0.969785 1.122575 0.067 Uiso 1 1 calc R U . . .
C4 C 0.05591(12) 0.8172(3) 1.05059(14) 0.0570(6) Uani 1 1 d . . . . .
H4 H 0.014059 0.834222 1.037089 0.068 Uiso 1 1 calc R U . . .
C5 C 0.07540(10) 0.7113(3) 1.01921(12) 0.0467(5) Uani 1 1 d . . . . .
C20 C -0.02578(12) 0.6560(4) 0.94089(18) 0.0983(13) Uani 1 1 d . . . . .
H20A H -0.047071 0.590473 0.904506 0.147 Uiso 1 1 calc R U . . .
H20B H -0.040347 0.646496 0.977528 0.147 Uiso 1 1 calc R U . . .
H20C H -0.033238 0.750313 0.922906 0.147 Uiso 1 1 calc R U . . .
C6 C 0.13882(9) 0.6816(2) 1.03886(10) 0.0355(4) Uani 1 1 d . . . . .
O2 O 0.15380(6) 0.58066(16) 1.00586(7) 0.0394(3) Uani 1 1 d . . . . .
C10 C 0.38989(13) 0.5487(3) 1.22444(13) 0.0625(7) Uani 1 1 d . . . . .
H10A H 0.351610 0.547906 1.230418 0.094 Uiso 1 1 calc R U . . .
H10B H 0.413751 0.467722 1.246828 0.094 Uiso 1 1 calc R U . . .
H10C H 0.412262 0.632857 1.244655 0.094 Uiso 1 1 calc R U . . .
C11 C 0.43737(11) 0.5461(3) 1.13662(16) 0.0628(7) Uani 1 1 d . . . . .
H11A H 0.428805 0.543654 1.087905 0.094 Uiso 1 1 calc R U . . .
H11B H 0.459895 0.630227 1.156553 0.094 Uiso 1 1 calc R U . . .
H11C H 0.461384 0.465092 1.158727 0.094 Uiso 1 1 calc R U . . .
O3 O 0.20247(6) 0.46174(14) 0.92293(7) 0.0370(3) Uani 1 1 d . . . . .
O2S O 0.000000 0.6488(5) 0.750000 0.136(2) Uani 1 2 d S T P . .
O3S O 0.500000 0.2307(4) 1.250000 0.1259(14) Uani 1 2 d S T P . .
H1S H 0.0972(15) 0.470(3) 0.8629(17) 0.053(10) Uiso 1 1 d . . . . .
H2S H 0.0684(18) 0.493(4) 0.900(2) 0.095(14) Uiso 1 1 d . . . . .
HS1 H -0.0156(19) 0.603(4) 0.724(2) 0.098(15) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 O2 1.8856(13) . ?
Cu1 O3 1.9005(14) . ?
Cu1 N2 1.9366(16) . ?
Cu1 N1 1.9416(17) . ?
O1S H1S 0.67(3) . ?
O1S H2S 0.76(4) . ?
O1 C5 1.357(3) . ?
O1 C20 1.420(3) . ?
O4 C16 1.358(3) . ?
O4 C21 1.413(3) . ?
N2 C13 1.285(3) . ?
N2 C12 1.454(2) . ?
C13 C14 1.432(3) . ?
C13 H13 0.9300 . ?
C14 C19 1.405(3) . ?
C14 C15 1.409(3) . ?
C16 C17 1.366(3) . ?
C16 C15 1.415(3) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C15 O3 1.305(2) . ?
C17 C18 1.379(4) . ?
C17 H17 0.9300 . ?
C18 C19 1.356(4) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C12 C9 1.538(3) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C9 C11 1.520(3) . ?
C9 C10 1.527(3) . ?
C9 C8 1.533(3) . ?
C8 N1 1.460(2) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
N1 C7 1.279(2) . ?
C7 C1 1.433(3) . ?
C7 H7 0.9300 . ?
C1 C6 1.408(3) . ?
C1 C2 1.411(3) . ?
C2 C3 1.352(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.375(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.375(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.418(3) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C6 O2 1.308(2) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
O2S HS1 0.69(4) . ?
O2S HS1 0.69(4) 2_556 ?

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 Cu1 O3 90.02(6) . . ?
O2 Cu1 N2 156.75(7) . . ?
O3 Cu1 N2 93.57(6) . . ?
O2 Cu1 N1 94.15(7) . . ?
O3 Cu1 N1 155.13(6) . . ?
N2 Cu1 N1 92.18(7) . . ?
H1S O1S H2S 119(4) . . ?
C5 O1 C20 117.2(2) . . ?
C16 O4 C21 118.11(19) . . ?
C13 N2 C12 120.21(17) . . ?
C13 N2 Cu1 125.18(14) . . ?
C12 N2 Cu1 114.07(13) . . ?
N2 C13 C14 126.07(18) . . ?
N2 C13 H13 117.0 . . ?
C14 C13 H13 117.0 . . ?
C19 C14 C15 119.5(2) . . ?
C19 C14 C13 118.40(19) . . ?
C15 C14 C13 122.08(18) . . ?
O4 C16 C17 124.3(2) . . ?
O4 C16 C15 114.00(18) . . ?
C17 C16 C15 121.7(2) . . ?
O4 C21 H21A 109.5 . . ?
O4 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
O4 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
O3 C15 C14 124.87(18) . . ?
O3 C15 C16 117.98(18) . . ?
C14 C15 C16 117.13(18) . . ?
C16 C17 C18 120.2(2) . . ?
C16 C17 H17 119.9 . . ?
C18 C17 H17 119.9 . . ?
C19 C18 C17 120.2(2) . . ?
C19 C18 H18 119.9 . . ?
C17 C18 H18 119.9 . . ?
C18 C19 C14 121.2(2) . . ?
C18 C19 H19 119.4 . . ?
C14 C19 H19 119.4 . . ?
N2 C12 C9 113.40(16) . . ?
N2 C12 H12A 108.9 . . ?
C9 C12 H12A 108.9 . . ?
N2 C12 H12B 108.9 . . ?
C9 C12 H12B 108.9 . . ?
H12A C12 H12B 107.7 . . ?
C11 C9 C10 110.3(2) . . ?
C11 C9 C8 107.57(18) . . ?
C10 C9 C8 110.3(2) . . ?
C11 C9 C12 109.9(2) . . ?
C10 C9 C12 107.01(18) . . ?
C8 C9 C12 111.80(17) . . ?
N1 C8 C9 115.14(16) . . ?
N1 C8 H8A 108.5 . . ?
C9 C8 H8A 108.5 . . ?
N1 C8 H8B 108.5 . . ?
C9 C8 H8B 108.5 . . ?
H8A C8 H8B 107.5 . . ?
C7 N1 C8 119.22(17) . . ?
C7 N1 Cu1 124.87(14) . . ?
C8 N1 Cu1 115.23(13) . . ?
N1 C7 C1 126.57(19) . . ?
N1 C7 H7 116.7 . . ?
C1 C7 H7 116.7 . . ?
C6 C1 C2 119.93(19) . . ?
C6 C1 C7 122.13(18) . . ?
C2 C1 C7 117.8(2) . . ?
C3 C2 C1 121.0(2) . . ?
C3 C2 H2 119.5 . . ?
C1 C2 H2 119.5 . . ?
C2 C3 C4 120.2(2) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 H3 119.9 . . ?
C3 C4 C5 120.6(2) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
O1 C5 C4 125.5(2) . . ?
O1 C5 C6 113.26(19) . . ?
C4 C5 C6 121.3(2) . . ?
O1 C20 H20A 109.5 . . ?
O1 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
O1 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
O2 C6 C1 125.33(18) . . ?
O2 C6 C5 117.69(19) . . ?
C1 C6 C5 116.96(19) . . ?
C6 O2 Cu1 126.84(13) . . ?
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 . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C15 O3 Cu1 126.07(13) . . ?
HS1 O2S HS1 101(7) . 2_556 ?

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
C12 N2 C13 C14 178.19(18) . . . . ?
Cu1 N2 C13 C14 7.1(3) . . . . ?
N2 C13 C14 C19 171.85(19) . . . . ?
N2 C13 C14 C15 -8.0(3) . . . . ?
C21 O4 C16 C17 14.6(3) . . . . ?
C21 O4 C16 C15 -165.8(2) . . . . ?
C19 C14 C15 O3 175.22(19) . . . . ?
C13 C14 C15 O3 -5.0(3) . . . . ?
C19 C14 C15 C16 -3.1(3) . . . . ?
C13 C14 C15 C16 176.67(18) . . . . ?
O4 C16 C15 O3 2.6(3) . . . . ?
C17 C16 C15 O3 -177.77(19) . . . . ?
O4 C16 C15 C14 -178.88(17) . . . . ?
C17 C16 C15 C14 0.7(3) . . . . ?
O4 C16 C17 C18 -179.4(2) . . . . ?
C15 C16 C17 C18 1.1(4) . . . . ?
C16 C17 C18 C19 -0.3(4) . . . . ?
C17 C18 C19 C14 -2.2(4) . . . . ?
C15 C14 C19 C18 4.0(3) . . . . ?
C13 C14 C19 C18 -175.8(2) . . . . ?
C13 N2 C12 C9 115.2(2) . . . . ?
Cu1 N2 C12 C9 -72.82(19) . . . . ?
N2 C12 C9 C11 -82.3(2) . . . . ?
N2 C12 C9 C10 157.92(19) . . . . ?
N2 C12 C9 C8 37.0(3) . . . . ?
C11 C9 C8 N1 155.0(2) . . . . ?
C10 C9 C8 N1 -84.7(2) . . . . ?
C12 C9 C8 N1 34.3(3) . . . . ?
C9 C8 N1 C7 121.3(2) . . . . ?
C9 C8 N1 Cu1 -67.7(2) . . . . ?
C8 N1 C7 C1 172.41(18) . . . . ?
Cu1 N1 C7 C1 2.4(3) . . . . ?
N1 C7 C1 C6 -1.5(3) . . . . ?
N1 C7 C1 C2 -177.98(19) . . . . ?
C6 C1 C2 C3 0.1(3) . . . . ?
C7 C1 C2 C3 176.7(2) . . . . ?
C1 C2 C3 C4 -0.2(4) . . . . ?
C2 C3 C4 C5 -0.1(4) . . . . ?
C20 O1 C5 C4 2.8(4) . . . . ?
C20 O1 C5 C6 -175.9(3) . . . . ?
C3 C4 C5 O1 -178.2(2) . . . . ?
C3 C4 C5 C6 0.5(4) . . . . ?
C2 C1 C6 O2 178.47(18) . . . . ?
C7 C1 C6 O2 2.0(3) . . . . ?
C2 C1 C6 C5 0.3(3) . . . . ?
C7 C1 C6 C5 -176.15(18) . . . . ?
O1 C5 C6 O2 -0.1(3) . . . . ?
C4 C5 C6 O2 -178.9(2) . . . . ?
O1 C5 C6 C1 178.2(2) . . . . ?
C4 C5 C6 C1 -0.6(3) . . . . ?
C1 C6 O2 Cu1 -3.6(3) . . . . ?
C5 C6 O2 Cu1 174.63(15) . . . . ?
O3 Cu1 O2 C6 -152.10(16) . . . . ?
N2 Cu1 O2 C6 108.8(2) . . . . ?
N1 Cu1 O2 C6 3.35(17) . . . . ?
C14 C15 O3 Cu1 17.0(3) . . . . ?
C16 C15 O3 Cu1 -164.62(13) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C8 H8B O2 0.97 2.64 3.407(3) 135.8 7_567
O1S H2S O1 0.76(4) 2.21(4) 2.928(3) 157(4) .
O1S H2S O2 0.76(4) 2.49(4) 3.017(3) 128(4) .
C8 H8B O2 0.97 2.64 3.407(3) 135.8 7_567

_refine_diff_density_max         0.302
_refine_diff_density_min         -0.390
_refine_diff_density_rms         0.056


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: DMSO'
