# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1943411'
loop_
_audit_author_name
_audit_author_address
'Hadi Rudbari' 'Isfahan University'
_audit_update_record             
;
2019-07-26 deposited with the CCDC.	2020-06-02 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            'C30 H24 Cl4 Cu N2 O2'
_chemical_formula_weight         649.85

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_H-M_alt        'C 2'
_space_group_name_Hall           'C 2y'

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

_cell_length_a                   13.976(3)
_cell_length_b                   10.721(2)
_cell_length_c                   10.339(2)
_cell_angle_alpha                90
_cell_angle_beta                 118.05(3)
_cell_angle_gamma                90
_cell_volume                     1367.2(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    6897
_cell_measurement_theta_min      2.52
_cell_measurement_theta_max      26.14

_exptl_crystal_description       irregular
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.579
_exptl_crystal_F_000             662
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.23
_exptl_absorpt_coefficient_mu    1.222
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.511
_exptl_absorpt_correction_T_max  0.822
_exptl_absorpt_process_details   'SADABS; Bruker, 2008'
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9194
_diffrn_reflns_av_unetI/netI     0.0485
_diffrn_reflns_av_R_equivalents  0.0577
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.517
_diffrn_reflns_theta_max         26.166
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2699
_reflns_number_gt                2513
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.895
_reflns_Friedel_fraction_max     0.995
_reflns_Friedel_fraction_full    1.000

_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, 2007)'
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0626P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.06(2)
_chemical_absolute_configuration rmad
_refine_ls_number_reflns         2699
_refine_ls_number_parameters     178
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0426
_refine_ls_R_factor_gt           0.0403
_refine_ls_wR_factor_ref         0.0991
_refine_ls_wR_factor_gt          0.0980
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_restrained_S_all      1.018
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.500000 0.94049(6) 0.000000 0.0372(2) Uani 1 2 d S T P . .
Cl1 Cl 0.83207(10) 1.09460(13) 0.37375(14) 0.0546(4) Uani 1 1 d . . . . .
Cl2 Cl 1.04855(11) 0.76759(18) 0.21146(18) 0.0710(5) Uani 1 1 d . . . . .
O1 O 0.6421(2) 0.9962(3) 0.1233(4) 0.0420(7) Uani 1 1 d . . . . .
C7 C 0.7312(3) 0.9483(5) 0.1336(4) 0.0370(9) Uani 1 1 d . . . . .
N1 N 0.5418(3) 0.8632(4) -0.1436(4) 0.0359(8) Uani 1 1 d . . . . .
C5 C 0.9287(3) 0.9325(6) 0.2719(5) 0.0476(11) Uani 1 1 d . . . . .
H5 H 0.993622 0.957397 0.350891 0.057 Uiso 1 1 calc R U . . .
C6 C 0.8328(4) 0.9855(5) 0.2497(5) 0.0420(11) Uani 1 1 d . . . . .
C1 C 0.6402(4) 0.8296(5) -0.1021(5) 0.0390(10) Uani 1 1 d . . . . .
H1 H 0.651734 0.777835 -0.165582 0.047 Uiso 1 1 calc R U . . .
C4 C 0.9284(4) 0.8427(5) 0.1772(6) 0.0465(11) Uani 1 1 d . . . . .
C2 C 0.7350(4) 0.8634(4) 0.0324(5) 0.0384(10) Uani 1 1 d . . . . .
C3 C 0.8335(4) 0.8087(5) 0.0569(5) 0.0441(11) Uani 1 1 d . . . . .
H3 H 0.834515 0.749553 -0.008314 0.053 Uiso 1 1 calc R U . . .
C9 C 0.4184(4) 0.9362(7) -0.3906(5) 0.0539(12) Uani 1 1 d . . . . .
H9A H 0.366673 0.910583 -0.487522 0.081 Uiso 1 1 calc R U . . .
H9B H 0.383981 0.990700 -0.351371 0.081 Uiso 1 1 calc R U . . .
H9C H 0.477212 0.979328 -0.394490 0.081 Uiso 1 1 calc R U . . .
C8 C 0.4610(4) 0.8244(5) -0.2950(5) 0.0424(11) Uani 1 1 d . . . . .
H8 H 0.499392 0.773308 -0.334455 0.051 Uiso 1 1 calc R U . . .
C10 C 0.3746(4) 0.7425(4) -0.2878(5) 0.0405(10) Uani 1 1 d . . . . .
C11 C 0.2644(4) 0.7600(5) -0.3777(5) 0.0483(12) Uani 1 1 d . . . . .
H11 H 0.240307 0.823787 -0.446770 0.058 Uiso 1 1 calc R U . . .
C14 C 0.3319(6) 0.5702(6) -0.1748(7) 0.0708(18) Uani 1 1 d . . . . .
H14 H 0.355026 0.506208 -0.106039 0.085 Uiso 1 1 calc R U . . .
C15 C 0.4065(5) 0.6453(5) -0.1877(6) 0.0565(14) Uani 1 1 d . . . . .
H15 H 0.480001 0.630671 -0.128091 0.068 Uiso 1 1 calc R U . . .
C12 C 0.1905(5) 0.6823(6) -0.3646(7) 0.0599(15) Uani 1 1 d . . . . .
H12 H 0.116847 0.693955 -0.426455 0.072 Uiso 1 1 calc R U . . .
C13 C 0.2229(5) 0.5897(7) -0.2638(7) 0.0703(17) Uani 1 1 d . . . . .
H13 H 0.171915 0.539714 -0.254839 0.084 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 O1 1.883(3) . ?
Cu1 O1 1.883(3) 2_655 ?
Cu1 N1 2.012(4) . ?
Cu1 N1 2.012(4) 2_655 ?
Cl1 C6 1.739(5) . ?
Cl2 C4 1.742(5) . ?
O1 C7 1.305(5) . ?
C7 C2 1.406(7) . ?
C7 C6 1.419(6) . ?
N1 C1 1.285(6) . ?
N1 C8 1.495(5) . ?
C5 C4 1.372(8) . ?
C5 C6 1.372(7) . ?
C5 H5 0.9300 . ?
C1 C2 1.445(6) . ?
C1 H1 0.9300 . ?
C4 C3 1.374(7) . ?
C2 C3 1.407(7) . ?
C3 H3 0.9300 . ?
C9 C8 1.488(8) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C8 C10 1.524(7) . ?
C8 H8 0.9800 . ?
C10 C15 1.386(7) . ?
C10 C11 1.387(7) . ?
C11 C12 1.382(8) . ?
C11 H11 0.9300 . ?
C14 C15 1.372(9) . ?
C14 C13 1.376(10) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C12 C13 1.354(9) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Cu1 O1 143.0(2) . 2_655 ?
O1 Cu1 N1 92.90(14) . . ?
O1 Cu1 N1 102.17(15) 2_655 . ?
O1 Cu1 N1 102.17(15) . 2_655 ?
O1 Cu1 N1 92.90(14) 2_655 2_655 ?
N1 Cu1 N1 131.3(2) . 2_655 ?
C7 O1 Cu1 126.3(3) . . ?
O1 C7 C2 124.2(4) . . ?
O1 C7 C6 119.6(4) . . ?
C2 C7 C6 116.1(4) . . ?
C1 N1 C8 115.8(4) . . ?
C1 N1 Cu1 120.3(3) . . ?
C8 N1 Cu1 123.3(3) . . ?
C4 C5 C6 119.8(4) . . ?
C4 C5 H5 120.1 . . ?
C6 C5 H5 120.1 . . ?
C5 C6 C7 122.3(5) . . ?
C5 C6 Cl1 119.9(4) . . ?
C7 C6 Cl1 117.6(4) . . ?
N1 C1 C2 127.2(4) . . ?
N1 C1 H1 116.4 . . ?
C2 C1 H1 116.4 . . ?
C5 C4 C3 120.7(4) . . ?
C5 C4 Cl2 120.0(4) . . ?
C3 C4 Cl2 119.3(4) . . ?
C7 C2 C3 120.8(4) . . ?
C7 C2 C1 122.7(4) . . ?
C3 C2 C1 116.5(4) . . ?
C4 C3 C2 119.9(5) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C9 C8 N1 109.9(4) . . ?
C9 C8 C10 114.7(4) . . ?
N1 C8 C10 109.6(4) . . ?
C9 C8 H8 107.4 . . ?
N1 C8 H8 107.5 . . ?
C10 C8 H8 107.4 . . ?
C15 C10 C11 117.9(5) . . ?
C15 C10 C8 119.0(4) . . ?
C11 C10 C8 123.0(4) . . ?
C12 C11 C10 119.9(5) . . ?
C12 C11 H11 120.1 . . ?
C10 C11 H11 120.1 . . ?
C15 C14 C13 119.9(6) . . ?
C15 C14 H14 120.0 . . ?
C13 C14 H14 120.0 . . ?
C14 C15 C10 121.4(5) . . ?
C14 C15 H15 119.3 . . ?
C10 C15 H15 119.3 . . ?
C13 C12 C11 121.5(6) . . ?
C13 C12 H12 119.2 . . ?
C11 C12 H12 119.2 . . ?
C12 C13 C14 119.3(6) . . ?
C12 C13 H13 120.3 . . ?
C14 C13 H13 120.3 . . ?

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
O1 Cu1 O1 C7 -139.6(4) 2_655 . . . ?
N1 Cu1 O1 C7 -24.9(4) . . . . ?
N1 Cu1 O1 C7 108.5(4) 2_655 . . . ?
Cu1 O1 C7 C2 14.0(6) . . . . ?
Cu1 O1 C7 C6 -168.5(3) . . . . ?
C4 C5 C6 C7 1.9(8) . . . . ?
C4 C5 C6 Cl1 177.3(4) . . . . ?
O1 C7 C6 C5 175.6(5) . . . . ?
C2 C7 C6 C5 -6.7(7) . . . . ?
O1 C7 C6 Cl1 0.1(6) . . . . ?
C2 C7 C6 Cl1 177.8(4) . . . . ?
C8 N1 C1 C2 174.2(4) . . . . ?
Cu1 N1 C1 C2 -14.3(7) . . . . ?
C6 C5 C4 C3 2.6(8) . . . . ?
C6 C5 C4 Cl2 -175.7(4) . . . . ?
O1 C7 C2 C3 -175.2(5) . . . . ?
C6 C7 C2 C3 7.2(7) . . . . ?
O1 C7 C2 C1 6.2(7) . . . . ?
C6 C7 C2 C1 -171.4(5) . . . . ?
N1 C1 C2 C7 -4.9(8) . . . . ?
N1 C1 C2 C3 176.4(5) . . . . ?
C5 C4 C3 C2 -2.0(8) . . . . ?
Cl2 C4 C3 C2 176.4(4) . . . . ?
C7 C2 C3 C4 -3.2(7) . . . . ?
C1 C2 C3 C4 175.5(4) . . . . ?
C1 N1 C8 C9 -113.0(5) . . . . ?
Cu1 N1 C8 C9 75.8(4) . . . . ?
C1 N1 C8 C10 120.1(5) . . . . ?
Cu1 N1 C8 C10 -51.1(5) . . . . ?
C9 C8 C10 C15 -171.9(5) . . . . ?
N1 C8 C10 C15 -47.7(6) . . . . ?
C9 C8 C10 C11 8.5(7) . . . . ?
N1 C8 C10 C11 132.7(5) . . . . ?
C15 C10 C11 C12 0.7(7) . . . . ?
C8 C10 C11 C12 -179.7(5) . . . . ?
C13 C14 C15 C10 0.9(10) . . . . ?
C11 C10 C15 C14 -1.6(9) . . . . ?
C8 C10 C15 C14 178.8(6) . . . . ?
C10 C11 C12 C13 1.0(8) . . . . ?
C11 C12 C13 C14 -1.7(10) . . . . ?
C15 C14 C13 C12 0.8(10) . . . . ?

_refine_diff_density_max         0.496
_refine_diff_density_min         -0.799
_refine_diff_density_rms         0.079

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

data_shelx_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1943419'
loop_
_audit_author_name
_audit_author_address
'Hadi Rudbari' 'Isfahan University'
_audit_update_record             
;
2019-07-26 deposited with the CCDC.	2020-06-02 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            'C30 H24 Br4 Cu N2 O2'
_chemical_formula_weight         827.69

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           5
_space_group_name_H-M_alt        'I 2'
_space_group_name_Hall           'I 2y'

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

_cell_length_a                   10.427(2)
_cell_length_b                   10.778(2)
_cell_length_c                   13.058(3)
_cell_angle_alpha                90
_cell_angle_beta                 106.74(3)
_cell_angle_gamma                90
_cell_volume                     1405.3(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    9468
_cell_measurement_theta_min      2.21
_cell_measurement_theta_max      31.60

_exptl_crystal_description       irregular
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.956
_exptl_crystal_F_000             806
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.17
_exptl_absorpt_coefficient_mu    6.496
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.312
_exptl_absorpt_correction_T_max  0.443
_exptl_absorpt_process_details   'SADABS; Bruker, 2008'
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14689
_diffrn_reflns_av_unetI/netI     0.0292
_diffrn_reflns_av_R_equivalents  0.0263
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.495
_diffrn_reflns_theta_max         26.996
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3060
_reflns_number_gt                2885
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.898
_reflns_Friedel_fraction_max     0.999
_reflns_Friedel_fraction_full    0.998

_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, 2007)'
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0194P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.020(9)
_chemical_absolute_configuration rmad
_refine_ls_number_reflns         3060
_refine_ls_number_parameters     178
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0207
_refine_ls_R_factor_gt           0.0185
_refine_ls_wR_factor_ref         0.0430
_refine_ls_wR_factor_gt          0.0424
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.037
_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
Cu1 Cu 0.500000 0.89077(5) 0.500000 0.02730(12) Uani 1 2 d S T P . .
Br1 Br 0.44555(3) 0.72782(3) 0.82740(3) 0.04020(10) Uani 1 1 d . . . . .
Br2 Br 0.83694(4) 1.07064(4) 1.05062(3) 0.05372(13) Uani 1 1 d . . . . .
C9 C 0.8088(3) 0.8969(4) 0.4197(3) 0.0431(8) Uani 1 1 d . . . . .
H9A H 0.853646 0.922295 0.368473 0.065 Uiso 1 1 calc R U . . .
H9B H 0.871081 0.855119 0.478128 0.065 Uiso 1 1 calc R U . . .
H9C H 0.736737 0.841587 0.386125 0.065 Uiso 1 1 calc R U . . .
C7 C 0.5964(3) 0.8805(3) 0.7276(2) 0.0260(6) Uani 1 1 d . . . . .
O1 O 0.5177(2) 0.8356(2) 0.63990(17) 0.0301(4) Uani 1 1 d . . . . .
N1 N 0.6835(2) 0.9697(2) 0.5409(2) 0.0277(5) Uani 1 1 d . . . . .
C6 C 0.5813(3) 0.8457(3) 0.8274(3) 0.0284(6) Uani 1 1 d . . . . .
C2 C 0.6999(3) 0.9671(3) 0.7312(2) 0.0280(6) Uani 1 1 d . . . . .
C10 C 0.6588(3) 1.0892(3) 0.3756(3) 0.0313(7) Uani 1 1 d . . . . .
C3 C 0.7720(3) 1.0214(3) 0.8289(3) 0.0329(7) Uani 1 1 d . . . . .
H3 H 0.836796 1.081075 0.829778 0.040 Uiso 1 1 calc R U . . .
C4 C 0.7479(3) 0.9875(3) 0.9222(3) 0.0347(7) Uani 1 1 d . . . . .
C15 C 0.5937(4) 1.1876(3) 0.4080(4) 0.0486(9) Uani 1 1 d . . . . .
H15 H 0.608444 1.203444 0.480525 0.058 Uiso 1 1 calc R U . . .
C1 C 0.7387(3) 1.0012(3) 0.6372(3) 0.0300(6) Uani 1 1 d . . . . .
H1 H 0.813314 1.052396 0.648725 0.036 Uiso 1 1 calc R U . . .
C8 C 0.7528(3) 1.0107(3) 0.4615(3) 0.0315(7) Uani 1 1 d . . . . .
H8 H 0.828677 1.063025 0.499082 0.038 Uiso 1 1 calc R U . . .
C11 C 0.6392(3) 1.0709(3) 0.2675(3) 0.0382(7) Uani 1 1 d . . . . .
H11 H 0.683231 1.006427 0.244309 0.046 Uiso 1 1 calc R U . . .
C12 C 0.5542(4) 1.1483(4) 0.1934(3) 0.0520(10) Uani 1 1 d . . . . .
H12 H 0.542478 1.135951 0.120746 0.062 Uiso 1 1 calc R U . . .
C5 C 0.6540(3) 0.8963(4) 0.9232(2) 0.0343(7) Uani 1 1 d . . . . .
H5 H 0.640653 0.870042 0.987239 0.041 Uiso 1 1 calc R U . . .
C13 C 0.4876(4) 1.2421(4) 0.2259(4) 0.0572(10) Uani 1 1 d . . . . .
H13 H 0.429181 1.292390 0.175655 0.069 Uiso 1 1 calc R U . . .
C14 C 0.5070(5) 1.2623(4) 0.3329(4) 0.0632(12) Uani 1 1 d . . . . .
H14 H 0.461673 1.326442 0.355139 0.076 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 O1 1.879(2) . ?
Cu1 O1 1.879(2) 2_656 ?
Cu1 N1 2.020(2) 2_656 ?
Cu1 N1 2.020(2) . ?
Br1 C6 1.902(3) . ?
Br2 C4 1.892(3) . ?
C9 C8 1.525(5) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C7 O1 1.296(4) . ?
C7 C6 1.408(4) . ?
C7 C2 1.417(4) . ?
N1 C1 1.269(4) . ?
N1 C8 1.491(4) . ?
C6 C5 1.375(4) . ?
C2 C3 1.409(4) . ?
C2 C1 1.446(4) . ?
C10 C11 1.381(5) . ?
C10 C15 1.390(5) . ?
C10 C8 1.517(4) . ?
C3 C4 1.363(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.391(5) . ?
C15 C14 1.385(6) . ?
C15 H15 0.9300 . ?
C1 H1 0.9300 . ?
C8 H8 0.9800 . ?
C11 C12 1.388(5) . ?
C11 H11 0.9300 . ?
C12 C13 1.362(6) . ?
C12 H12 0.9300 . ?
C5 H5 0.9300 . ?
C13 C14 1.370(6) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Cu1 O1 143.07(14) . 2_656 ?
O1 Cu1 N1 102.18(10) . 2_656 ?
O1 Cu1 N1 93.19(10) 2_656 2_656 ?
O1 Cu1 N1 93.19(10) . . ?
O1 Cu1 N1 102.18(10) 2_656 . ?
N1 Cu1 N1 130.20(14) 2_656 . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
O1 C7 C6 120.5(3) . . ?
O1 C7 C2 123.9(3) . . ?
C6 C7 C2 115.6(3) . . ?
C7 O1 Cu1 126.94(19) . . ?
C1 N1 C8 115.9(3) . . ?
C1 N1 Cu1 120.0(2) . . ?
C8 N1 Cu1 123.6(2) . . ?
C5 C6 C7 123.9(3) . . ?
C5 C6 Br1 118.7(2) . . ?
C7 C6 Br1 117.3(2) . . ?
C3 C2 C7 120.4(3) . . ?
C3 C2 C1 117.1(3) . . ?
C7 C2 C1 122.4(3) . . ?
C11 C10 C15 118.6(3) . . ?
C11 C10 C8 123.4(3) . . ?
C15 C10 C8 118.0(3) . . ?
C4 C3 C2 120.7(3) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C3 C4 C5 120.7(3) . . ?
C3 C4 Br2 119.7(3) . . ?
C5 C4 Br2 119.6(2) . . ?
C14 C15 C10 120.3(4) . . ?
C14 C15 H15 119.8 . . ?
C10 C15 H15 119.8 . . ?
N1 C1 C2 127.9(3) . . ?
N1 C1 H1 116.0 . . ?
C2 C1 H1 116.0 . . ?
N1 C8 C10 109.9(2) . . ?
N1 C8 C9 108.8(3) . . ?
C10 C8 C9 114.6(3) . . ?
N1 C8 H8 107.8 . . ?
C10 C8 H8 107.8 . . ?
C9 C8 H8 107.8 . . ?
C10 C11 C12 120.3(4) . . ?
C10 C11 H11 119.9 . . ?
C12 C11 H11 119.9 . . ?
C13 C12 C11 120.6(4) . . ?
C13 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
C6 C5 C4 118.5(3) . . ?
C6 C5 H5 120.8 . . ?
C4 C5 H5 120.8 . . ?
C12 C13 C14 119.8(4) . . ?
C12 C13 H13 120.1 . . ?
C14 C13 H13 120.1 . . ?
C13 C14 C15 120.3(4) . . ?
C13 C14 H14 119.8 . . ?
C15 C14 H14 119.8 . . ?

_refine_diff_density_max         0.460
_refine_diff_density_min         -0.200
_refine_diff_density_rms         0.054

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

data_har003
_database_code_depnum_ccdc_archive 'CCDC 1943413'
loop_
_audit_author_name
_audit_author_address
'Hadi Rudbari' 'Isfahan University'
_audit_update_record             
;
2019-07-26 deposited with the CCDC.	2020-06-02 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         'C30 H24 Br4 Cu N2 O2'
_chemical_formula_sum            'C30 H24 Br4 Cu N2 O2'
_chemical_formula_weight         827.69

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      monoclinic
_space_group_IT_number           5
_space_group_name_H-M_alt        'C 2'
_space_group_name_Hall           'C 2y'

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

_cell_length_a                   14.1169(5)
_cell_length_b                   10.7071(4)
_cell_length_c                   10.3296(4)
_cell_angle_alpha                90
_cell_angle_beta                 117.7800(10)
_cell_angle_gamma                90
_cell_volume                     1381.38(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9950
_cell_measurement_theta_min      2.51
_cell_measurement_theta_max      33.32

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.990
_exptl_crystal_F_000             806
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.310
_exptl_crystal_size_mid          0.310
_exptl_crystal_size_min          0.090
_exptl_absorpt_coefficient_mu    6.609
_shelx_estimated_absorpt_T_min   0.234
_shelx_estimated_absorpt_T_max   0.588
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4057
_exptl_absorpt_correction_T_max  0.7465
_exptl_absorpt_process_details   'SADABS V2014/5 (Bruker AXS Inc.)'
_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 D8 QUEST ECO CMOS'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            25601
_diffrn_reflns_av_unetI/netI     0.0392
_diffrn_reflns_av_R_equivalents  0.0393
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.506
_diffrn_reflns_theta_max         33.326
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             5317
_reflns_number_gt                4907
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.914
_reflns_Friedel_fraction_max     1.000
_reflns_Friedel_fraction_full    0.999

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

_computing_data_collection       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
; 
 Refined as a 2-component inversion twin. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0172P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
; 
 Refined as an inversion twin. 
;
_refine_ls_abs_structure_Flack   0.025(8)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         5317
_refine_ls_number_parameters     179
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0290
_refine_ls_R_factor_gt           0.0237
_refine_ls_wR_factor_ref         0.0491
_refine_ls_wR_factor_gt          0.0473
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.041
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.82787(2) 0.76747(3) 0.88517(3) 0.01917(6) Uani 1 1 d . . . . .
Br2 Br 1.05214(2) 0.42155(3) 0.71450(3) 0.02532(8) Uani 1 1 d . . . . .
C1 C 0.6383(2) 0.4922(2) 0.3979(3) 0.0156(4) Uani 1 1 d . . . . .
H1 H 0.6499 0.4386 0.3334 0.019 Uiso 1 1 calc R U . . .
C2 C 0.7320(2) 0.5266(2) 0.5317(3) 0.0147(4) Uani 1 1 d . . . . .
C3 C 0.8294(2) 0.4711(2) 0.5561(3) 0.0171(5) Uani 1 1 d . . . . .
H3 H 0.8301 0.4099 0.4899 0.021 Uiso 1 1 calc R U . . .
C4 C 0.9236(2) 0.5052(3) 0.6754(3) 0.0173(5) Uani 1 1 d . . . . .
C5 C 0.92471(19) 0.5982(3) 0.7710(3) 0.0172(4) Uani 1 1 d . . . . .
H5 H 0.9903 0.6251 0.8500 0.021 Uiso 1 1 calc R U . . .
C6 C 0.8286(2) 0.6503(2) 0.7486(3) 0.0152(4) Uani 1 1 d . . . . .
C7 C 0.72824(19) 0.6142(2) 0.6326(3) 0.0135(4) Uani 1 1 d . . . . .
C8 C 0.4615(2) 0.4848(3) 0.2067(3) 0.0165(4) Uani 1 1 d . . . . .
H8 H 0.5001 0.4309 0.1675 0.020 Uiso 1 1 calc R U . . .
C9 C 0.4197(2) 0.5983(3) 0.1077(3) 0.0223(5) Uani 1 1 d . . . . .
H9A H 0.3825 0.6538 0.1446 0.033 Uiso 1 1 calc R U . . .
H9B H 0.3698 0.5712 0.0082 0.033 Uiso 1 1 calc R U . . .
H9C H 0.4798 0.6430 0.1062 0.033 Uiso 1 1 calc R U . . .
C10 C 0.3760(2) 0.4053(2) 0.2163(3) 0.0163(4) Uani 1 1 d . . . . .
C11 C 0.2670(2) 0.4246(3) 0.1265(3) 0.0193(5) Uani 1 1 d . . . . .
H11 H 0.2436 0.4908 0.0573 0.023 Uiso 1 1 calc R U . . .
C12 C 0.1924(2) 0.3470(3) 0.1380(4) 0.0249(6) Uani 1 1 d . . . . .
H12 H 0.1182 0.3595 0.0751 0.030 Uiso 1 1 calc R U . . .
C13 C 0.2251(3) 0.2519(3) 0.2400(4) 0.0304(6) Uani 1 1 d . . . . .
H13 H 0.1735 0.2012 0.2498 0.036 Uiso 1 1 calc R U . . .
C14 C 0.3333(3) 0.2307(3) 0.3280(4) 0.0304(7) Uani 1 1 d . . . . .
H14 H 0.3563 0.1645 0.3971 0.037 Uiso 1 1 calc R U . . .
C15 C 0.4081(3) 0.3064(3) 0.3148(3) 0.0244(6) Uani 1 1 d . . . . .
H15 H 0.4823 0.2904 0.3740 0.029 Uiso 1 1 calc R U . . .
Cu1 Cu 0.5000 0.60535(4) 0.5000 0.01381(9) Uani 1 2 d S T P . .
N1 N 0.54091(18) 0.5261(2) 0.3564(2) 0.0148(4) Uani 1 1 d . . . . .
O1 O 0.64034(15) 0.66011(18) 0.6237(2) 0.0166(3) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C6 1.892(3) . ?
Br2 C4 1.891(3) . ?
C1 N1 1.286(4) . ?
C1 C2 1.447(4) . ?
C1 H1 0.9500 . ?
C2 C3 1.409(4) . ?
C2 C7 1.421(4) . ?
C3 C4 1.375(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.397(4) . ?
C5 C6 1.383(4) . ?
C5 H5 0.9500 . ?
C6 C7 1.418(3) . ?
C7 O1 1.297(3) . ?
C8 N1 1.492(3) . ?
C8 C10 1.517(4) . ?
C8 C9 1.519(4) . ?
C8 H8 1.0000 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C15 1.390(4) . ?
C10 C11 1.393(4) . ?
C11 C12 1.389(4) . ?
C11 H11 0.9500 . ?
C12 C13 1.381(5) . ?
C12 H12 0.9500 . ?
C13 C14 1.385(5) . ?
C13 H13 0.9500 . ?
C14 C15 1.387(5) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
Cu1 O1 1.8819(19) 2_656 ?
Cu1 O1 1.8819(19) . ?
Cu1 N1 2.013(2) . ?
Cu1 N1 2.013(2) 2_656 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C2 127.3(2) . . ?
N1 C1 H1 116.3 . . ?
C2 C1 H1 116.3 . . ?
C3 C2 C7 121.0(2) . . ?
C3 C2 C1 116.4(2) . . ?
C7 C2 C1 122.6(2) . . ?
C4 C3 C2 120.2(2) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C3 C4 C5 120.7(2) . . ?
C3 C4 Br2 119.7(2) . . ?
C5 C4 Br2 119.5(2) . . ?
C6 C5 C4 118.8(2) . . ?
C6 C5 H5 120.6 . . ?
C4 C5 H5 120.6 . . ?
C5 C6 C7 123.2(2) . . ?
C5 C6 Br1 119.25(19) . . ?
C7 C6 Br1 117.39(19) . . ?
O1 C7 C6 120.2(2) . . ?
O1 C7 C2 124.0(2) . . ?
C6 C7 C2 115.8(2) . . ?
N1 C8 C10 109.5(2) . . ?
N1 C8 C9 109.3(2) . . ?
C10 C8 C9 114.9(2) . . ?
N1 C8 H8 107.6 . . ?
C10 C8 H8 107.6 . . ?
C9 C8 H8 107.6 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C15 C10 C11 118.8(3) . . ?
C15 C10 C8 118.5(2) . . ?
C11 C10 C8 122.6(2) . . ?
C12 C11 C10 120.1(3) . . ?
C12 C11 H11 120.0 . . ?
C10 C11 H11 120.0 . . ?
C13 C12 C11 120.6(3) . . ?
C13 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
C12 C13 C14 119.7(3) . . ?
C12 C13 H13 120.2 . . ?
C14 C13 H13 120.2 . . ?
C13 C14 C15 119.9(3) . . ?
C13 C14 H14 120.1 . . ?
C15 C14 H14 120.1 . . ?
C14 C15 C10 120.9(3) . . ?
C14 C15 H15 119.6 . . ?
C10 C15 H15 119.6 . . ?
O1 Cu1 O1 143.69(12) 2_656 . ?
O1 Cu1 N1 101.77(9) 2_656 . ?
O1 Cu1 N1 93.37(9) . . ?
O1 Cu1 N1 93.37(9) 2_656 2_656 ?
O1 Cu1 N1 101.77(9) . 2_656 ?
N1 Cu1 N1 130.12(12) . 2_656 ?
C1 N1 C8 115.6(2) . . ?
C1 N1 Cu1 120.14(18) . . ?
C8 N1 Cu1 123.59(17) . . ?
C7 O1 Cu1 126.84(16) . . ?

_refine_diff_density_max         0.616
_refine_diff_density_min         -0.508
_refine_diff_density_rms         0.082

####################################################################### 
# 
# 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_c4
_database_code_depnum_ccdc_archive 'CCDC 1943417'
loop_
_audit_author_name
_audit_author_address
'Hadi Rudbari' 'Isfahan University'
_audit_update_record             
;
2019-07-26 deposited with the CCDC.	2020-06-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C30 H24 Br2 Cl2 Cu N2 O2'
_chemical_formula_sum            'C30 H24 Br2 Cl2 Cu N2 O2'
_chemical_formula_weight         738.77

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu -1.9646 0.5888 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_H-M_alt        'I 2'
_space_group_name_Hall           'I 2y'

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

_cell_length_a                   10.33616(17)
_cell_length_b                   10.64041(15)
_cell_length_c                   13.0212(2)
_cell_angle_alpha                90
_cell_angle_beta                 107.5551(17)
_cell_angle_gamma                90
_cell_volume                     1365.39(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    140.00(10)
_cell_measurement_reflns_used    3897
_cell_measurement_theta_min      4.8120
_cell_measurement_theta_max      75.9990

_exptl_crystal_description       plate
_exptl_crystal_colour            'clear intense green'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.797
_exptl_crystal_F_000             734
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.461
_exptl_crystal_size_mid          0.322
_exptl_crystal_size_min          0.151
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
6 -3 -1 0.0775
-6 4 1 0.0540
2 1 -8 0.2165
1 -4 -6 0.1713
0 -7 0 0.1330
-2 -3 8 0.2209
-2 0 8 0.2001
0 7 0 0.1420
4 6 -2 0.1579
-3 -5 -3 0.1377
-4 -6 1 0.1437
-1 0 8 0.2137
4 5 -4 0.1642
-5 -3 -3 0.1301
6 4 -3 0.1485
5 3 -6 0.1809
0 0 8 0.2263
6 4 -2 0.1596
5 1 -7 0.1787
7 0 -2 0.1212
2 -2 7 0.2079
6 -2 -1 0.0903
5 -1 -7 0.1596
-1 7 0 0.1235
_exptl_absorpt_coefficient_mu    6.623
_shelx_estimated_absorpt_T_min   0.150
_shelx_estimated_absorpt_T_max   0.435
_exptl_absorpt_correction_T_min  0.190
_exptl_absorpt_correction_T_max  0.494
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      140.00(10)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            AtlasS2
_diffrn_detector_area_resol_mean 5.2817
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -110.00 -16.00   1.00    1.00    --  -40.91 -57.00 -60.00   94
  2  ω    -97.00 -13.00   1.00    1.00    --  -40.91 -57.00  90.00   84
  3  ω   -115.00 -16.00   1.00    1.00    --  -40.91 -38.00-180.00   99
  4  ω     48.00  85.00   1.00    1.00    --   40.91-125.00 -90.00   37
  5  ω      2.00  72.00   1.00    1.00    --   40.91 -99.00  60.00   70
  6  ω     45.00  83.00   1.00    4.00    --  112.00 -45.00 -60.00   38
  7  ω    120.00 178.00   1.00    4.00    --  112.00  77.00  90.00   58
  8  ω     49.00 118.00   1.00    4.00    --  112.00-125.00 -90.00   69
  9  ω     94.00 153.00   1.00    4.00    --  112.00 125.00  30.00   59
 10  ω     35.00 109.00   1.00    4.00    --  112.00 -94.00 -60.00   74
 11  ω     86.00 167.00   1.00    4.00    --  112.00  45.00 150.00   81
 12  ω     36.00 140.00   1.00    4.00    --  112.00 -30.00 -30.00  104
 13  ω    111.00 138.00   1.00    4.00    --  112.00  30.00-120.00   27
 14  ω     64.00  91.00   1.00    4.00    --  112.00-125.00-150.00   27
 15  ω     33.00 101.00   1.00    4.00    --  112.00 -94.00 120.00   68
 16  ω     48.00 125.00   1.00    4.00    --  112.00 -30.00  90.00   77
 17  ω     58.00 112.00   1.00    4.00    --  112.00-125.00  90.00   54
;
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_number            4427
_diffrn_reflns_av_unetI/netI     0.0191
_diffrn_reflns_av_R_equivalents  0.0143
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         4.815
_diffrn_reflns_theta_max         76.200
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.912
_diffrn_reflns_point_group_measured_fraction_full 0.948
_reflns_number_total             2606
_reflns_number_gt                2591
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.763
_reflns_Friedel_fraction_max     0.836
_reflns_Friedel_fraction_full    0.890

_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       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Mercury 4.1.0 (CCDC, 2019)'
_computing_publication_material  'CIFTab (Sheldrick, 2015)'
_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)+(0.0493P)²+0.9429P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.00061(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 1113 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.03(2)
_chemical_absolute_configuration rmad
_refine_ls_number_reflns         2606
_refine_ls_number_parameters     178
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0248
_refine_ls_R_factor_gt           0.0247
_refine_ls_wR_factor_ref         0.0654
_refine_ls_wR_factor_gt          0.0654
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      1.059
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.55677(3) 0.23441(4) 0.17085(2) 0.02051(14) Uani 1 1 d . . . . .
Cu1 Cu 0.500000 0.39572(7) 0.500000 0.01522(18) Uani 1 2 d S T P . .
Cl1 Cl 0.16265(10) 0.57245(11) -0.04760(7) 0.0288(2) Uani 1 1 d . . . . .
O1 O 0.4824(3) 0.3409(3) 0.3584(2) 0.0178(5) Uani 1 1 d . . . . .
N1 N 0.3137(3) 0.4731(3) 0.4566(3) 0.0160(6) Uani 1 1 d . . . . .
C1 C 0.2567(3) 0.5084(4) 0.3593(3) 0.0175(7) Uani 1 1 d . . . . .
H1 H 0.179778 0.561592 0.347478 0.021 Uiso 1 1 calc R U . . .
C2 C 0.2975(4) 0.4756(4) 0.2652(3) 0.0168(7) Uani 1 1 d . . . . .
C3 C 0.2228(4) 0.5311(4) 0.1666(3) 0.0201(7) Uani 1 1 d . . . . .
H3 H 0.155016 0.591870 0.165452 0.024 Uiso 1 1 calc R U . . .
C4 C 0.2477(4) 0.4977(4) 0.0721(3) 0.0203(7) Uani 1 1 d . . . . .
C5 C 0.3442(4) 0.4048(4) 0.0724(3) 0.0198(7) Uani 1 1 d . . . . .
H5 H 0.358752 0.378516 0.007053 0.024 Uiso 1 1 calc R U . . .
C6 C 0.4174(4) 0.3526(4) 0.1691(3) 0.0170(7) Uani 1 1 d . . . . .
C7 C 0.4020(4) 0.3880(4) 0.2692(3) 0.0161(7) Uani 1 1 d . . . . .
C8 C 0.2434(4) 0.5123(4) 0.5364(3) 0.0179(7) Uani 1 1 d . . . . .
H8 H 0.163821 0.565260 0.497468 0.021 Uiso 1 1 calc R U . . .
C9 C 0.1891(4) 0.3961(4) 0.5773(3) 0.0223(7) Uani 1 1 d . . . . .
H9A H 0.142836 0.420963 0.629661 0.033 Uiso 1 1 calc R U . . .
H9B H 0.124892 0.352702 0.516696 0.033 Uiso 1 1 calc R U . . .
H9C H 0.264566 0.339619 0.611914 0.033 Uiso 1 1 calc R U . . .
C10 C 0.3377(4) 0.5932(4) 0.6226(3) 0.0185(7) Uani 1 1 d . . . . .
C11 C 0.3567(4) 0.5751(4) 0.7325(3) 0.0222(7) Uani 1 1 d . . . . .
H11 H 0.310591 0.508954 0.755957 0.027 Uiso 1 1 calc R U . . .
C12 C 0.4431(4) 0.6539(4) 0.8072(3) 0.0264(8) Uani 1 1 d . . . . .
H12 H 0.454947 0.641576 0.881787 0.032 Uiso 1 1 calc R U . . .
C13 C 0.5119(4) 0.7499(5) 0.7754(3) 0.0318(9) Uani 1 1 d . . . . .
H13 H 0.572283 0.801940 0.827629 0.038 Uiso 1 1 calc R U . . .
C14 C 0.4924(5) 0.7699(4) 0.6662(4) 0.0310(9) Uani 1 1 d . . . . .
H14 H 0.539094 0.836033 0.643353 0.037 Uiso 1 1 calc R U . . .
C15 C 0.4045(5) 0.6929(4) 0.5907(3) 0.0248(8) Uani 1 1 d . . . . .
H15 H 0.389584 0.708211 0.516179 0.030 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C6 1.907(4) . ?
Cu1 O1 1.889(3) 2_656 ?
Cu1 O1 1.889(3) . ?
Cu1 N1 2.012(3) . ?
Cu1 N1 2.012(3) 2_656 ?
Cl1 C4 1.734(4) . ?
O1 C7 1.308(5) . ?
N1 C1 1.282(5) . ?
N1 C8 1.496(4) . ?
C1 C2 1.453(5) . ?
C2 C3 1.413(5) . ?
C2 C7 1.416(5) . ?
C3 C4 1.378(6) . ?
C4 C5 1.403(6) . ?
C5 C6 1.375(5) . ?
C6 C7 1.411(5) . ?
C8 C10 1.514(5) . ?
C8 C9 1.519(6) . ?
C10 C15 1.395(6) . ?
C10 C11 1.398(5) . ?
C11 C12 1.387(6) . ?
C12 C13 1.378(7) . ?
C13 C14 1.392(6) . ?
C14 C15 1.387(6) . ?

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 144.06(18) 2_656 . ?
O1 Cu1 N1 101.68(12) 2_656 . ?
O1 Cu1 N1 92.87(12) . . ?
O1 Cu1 N1 92.87(12) 2_656 2_656 ?
O1 Cu1 N1 101.68(12) . 2_656 ?
N1 Cu1 N1 131.71(19) . 2_656 ?
C7 O1 Cu1 126.7(2) . . ?
C1 N1 C8 115.5(3) . . ?
C1 N1 Cu1 120.9(2) . . ?
C8 N1 Cu1 122.9(2) . . ?
N1 C1 C2 126.8(3) . . ?
C3 C2 C7 120.6(3) . . ?
C3 C2 C1 116.6(3) . . ?
C7 C2 C1 122.7(3) . . ?
C4 C3 C2 120.4(4) . . ?
C3 C4 C5 120.2(3) . . ?
C3 C4 Cl1 120.2(3) . . ?
C5 C4 Cl1 119.6(3) . . ?
C6 C5 C4 118.8(3) . . ?
C5 C6 C7 123.6(4) . . ?
C5 C6 Br1 118.8(3) . . ?
C7 C6 Br1 117.4(3) . . ?
O1 C7 C6 120.0(3) . . ?
O1 C7 C2 123.9(3) . . ?
C6 C7 C2 116.1(3) . . ?
N1 C8 C10 109.5(3) . . ?
N1 C8 C9 108.9(3) . . ?
C10 C8 C9 115.3(3) . . ?
C15 C10 C11 118.7(4) . . ?
C15 C10 C8 118.5(3) . . ?
C11 C10 C8 122.7(3) . . ?
C12 C11 C10 119.8(4) . . ?
C13 C12 C11 121.3(4) . . ?
C12 C13 C14 119.5(4) . . ?
C15 C14 C13 119.7(4) . . ?
C14 C15 C10 121.0(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
O1 Cu1 O1 C7 138.1(3) 2_656 . . . ?
N1 Cu1 O1 C7 23.6(3) . . . . ?
N1 Cu1 O1 C7 -110.1(3) 2_656 . . . ?
C8 N1 C1 C2 -175.1(3) . . . . ?
Cu1 N1 C1 C2 14.5(5) . . . . ?
N1 C1 C2 C3 -176.9(4) . . . . ?
N1 C1 C2 C7 6.1(6) . . . . ?
C7 C2 C3 C4 2.1(6) . . . . ?
C1 C2 C3 C4 -174.9(4) . . . . ?
C2 C3 C4 C5 2.3(6) . . . . ?
C2 C3 C4 Cl1 -176.3(3) . . . . ?
C3 C4 C5 C6 -3.0(6) . . . . ?
Cl1 C4 C5 C6 175.6(3) . . . . ?
C4 C5 C6 C7 -0.6(6) . . . . ?
C4 C5 C6 Br1 -176.0(3) . . . . ?
Cu1 O1 C7 C6 168.5(3) . . . . ?
Cu1 O1 C7 C2 -11.1(5) . . . . ?
C5 C6 C7 O1 -174.8(4) . . . . ?
Br1 C6 C7 O1 0.6(5) . . . . ?
C5 C6 C7 C2 4.7(6) . . . . ?
Br1 C6 C7 C2 -179.8(3) . . . . ?
C3 C2 C7 O1 174.2(3) . . . . ?
C1 C2 C7 O1 -9.0(6) . . . . ?
C3 C2 C7 C6 -5.4(5) . . . . ?
C1 C2 C7 C6 171.5(3) . . . . ?
C1 N1 C8 C10 -119.8(3) . . . . ?
Cu1 N1 C8 C10 50.3(4) . . . . ?
C1 N1 C8 C9 113.3(4) . . . . ?
Cu1 N1 C8 C9 -76.6(3) . . . . ?
N1 C8 C10 C15 49.1(4) . . . . ?
C9 C8 C10 C15 172.3(3) . . . . ?
N1 C8 C10 C11 -133.3(4) . . . . ?
C9 C8 C10 C11 -10.1(5) . . . . ?
C15 C10 C11 C12 -1.4(6) . . . . ?
C8 C10 C11 C12 -179.0(3) . . . . ?
C10 C11 C12 C13 -0.5(6) . . . . ?
C11 C12 C13 C14 1.4(7) . . . . ?
C12 C13 C14 C15 -0.3(7) . . . . ?
C13 C14 C15 C10 -1.7(7) . . . . ?
C11 C10 C15 C14 2.5(6) . . . . ?
C8 C10 C15 C14 -179.8(4) . . . . ?

_refine_diff_density_max         0.580
_refine_diff_density_min         -0.471
_refine_diff_density_rms         0.068

####################################################################### 
# 
# 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_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 1943412'
loop_
_audit_author_name
_audit_author_address
'Hadi Rudbari' 'Isfahan University'
_audit_update_record             
;
2019-07-26 deposited with the CCDC.	2020-06-02 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            'C30 H24 Br2 Cl2 Cu N2 O2'
_chemical_formula_weight         738.77

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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           5
_space_group_name_H-M_alt        'C 2'
_space_group_name_Hall           'C 2y'

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

_cell_length_a                   14.040(3)
_cell_length_b                   10.708(2)
_cell_length_c                   10.439(2)
_cell_angle_alpha                90
_cell_angle_beta                 117.772(3)
_cell_angle_gamma                90
_cell_volume                     1388.6(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    2817
_cell_measurement_theta_min      2.61
_cell_measurement_theta_max      27.11

_exptl_crystal_description       irregular
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.767
_exptl_crystal_F_000             734
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.14
_exptl_absorpt_coefficient_mu    3.889
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.478
_exptl_absorpt_correction_T_max  0.632
_exptl_absorpt_process_details   'SADABS; Bruker, 2008'
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            21440
_diffrn_reflns_av_unetI/netI     0.0239
_diffrn_reflns_av_R_equivalents  0.0268
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.793
_diffrn_reflns_theta_max         26.980
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3009
_reflns_number_gt                2899
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.899
_reflns_Friedel_fraction_max     0.999
_reflns_Friedel_fraction_full    0.998

_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, 2007)'
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0268P)²+0.2246P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.032(9)
_chemical_absolute_configuration rmad
_refine_ls_number_reflns         3009
_refine_ls_number_parameters     179
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0207
_refine_ls_R_factor_gt           0.0193
_refine_ls_wR_factor_ref         0.0483
_refine_ls_wR_factor_gt          0.0474
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_restrained_S_all      1.057
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.500000 1.02659(4) 0.500000 0.02718(12) Uani 1 2 d S T P . .
Br1 Br 0.17143(2) 1.18911(3) 0.11788(3) 0.04148(10) Uani 1 1 d . . . . .
Cl1 Cl -0.04559(7) 0.85486(12) 0.29095(11) 0.0609(3) Uani 1 1 d . . . . .
C6 C 0.1695(3) 1.0706(3) 0.2525(3) 0.0312(6) Uani 1 1 d . . . . .
O1 O 0.35903(17) 1.0816(2) 0.3772(2) 0.0314(4) Uani 1 1 d . . . . .
C7 C 0.2705(2) 1.0362(3) 0.3678(3) 0.0273(5) Uani 1 1 d . . . . .
C1 C 0.6397(2) 0.9169(3) 0.3989(3) 0.0309(6) Uani 1 1 d . . . . .
H1 H 0.651374 0.865547 0.335771 0.037 Uiso 1 1 calc R U . . .
N1 N 0.5424(2) 0.9500(2) 0.3576(2) 0.0276(5) Uani 1 1 d . . . . .
C4 C 0.0742(3) 0.9290(3) 0.3253(4) 0.0381(7) Uani 1 1 d . . . . .
C5 C 0.0738(2) 1.0201(3) 0.2297(3) 0.0376(6) Uani 1 1 d . . . . .
H5 H 0.009645 1.045799 0.152047 0.045 Uiso 1 1 calc R U . . .
C2 C 0.2658(2) 0.9498(3) 0.4678(3) 0.0297(6) Uani 1 1 d . . . . .
C9 C 0.4224(3) 1.0259(4) 0.1147(3) 0.0443(7) Uani 1 1 d . . . . .
H9A H 0.384474 1.078297 0.150430 0.067 Uiso 1 1 calc R U . . .
H9B H 0.374582 1.001290 0.017052 0.067 Uiso 1 1 calc R U . . .
H9C H 0.482152 1.071025 0.116852 0.067 Uiso 1 1 calc R U . . .
C3 C 0.1680(3) 0.8958(3) 0.4440(3) 0.0359(7) Uani 1 1 d . . . . .
H3 H 0.166727 0.837315 0.509014 0.043 Uiso 1 1 calc R U . . .
C8 C 0.4631(3) 0.9109(3) 0.2090(3) 0.0330(6) Uani 1 1 d . . . . .
H8 H 0.501172 0.859216 0.170031 0.040 Uiso 1 1 calc R U . . .
C11 C 0.2677(3) 0.8480(3) 0.1254(3) 0.0399(7) Uani 1 1 d . . . . .
H11 H 0.244537 0.912403 0.057799 0.048 Uiso 1 1 calc R U . . .
C10 C 0.3768(3) 0.8309(3) 0.2159(3) 0.0331(6) Uani 1 1 d . . . . .
C15 C 0.4076(3) 0.7323(3) 0.3129(4) 0.0489(9) Uani 1 1 d . . . . .
H15 H 0.480379 0.716737 0.371682 0.059 Uiso 1 1 calc R U . . .
C13 C 0.2249(4) 0.6765(4) 0.2341(4) 0.0641(11) Uani 1 1 d . . . . .
H13 H 0.173801 0.625743 0.241207 0.077 Uiso 1 1 calc R U . . .
C12 C 0.1933(3) 0.7697(4) 0.1354(4) 0.0542(10) Uani 1 1 d . . . . .
H12 H 0.120424 0.781175 0.073265 0.065 Uiso 1 1 calc R U . . .
C14 C 0.3322(4) 0.6568(4) 0.3237(5) 0.0669(12) Uani 1 1 d . . . . .
H14 H 0.354127 0.592761 0.391611 0.080 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 O1 1.882(2) 2_656 ?
Cu1 O1 1.882(2) . ?
Cu1 N1 2.016(2) 2_656 ?
Cu1 N1 2.016(2) . ?
Br1 C6 1.903(3) . ?
Cl1 C4 1.739(3) . ?
C6 C5 1.362(5) . ?
C6 C7 1.415(4) . ?
O1 C7 1.295(3) . ?
C7 C2 1.419(4) . ?
C1 N1 1.275(4) . ?
C1 C2 1.449(4) 2_656 ?
N1 C8 1.487(3) . ?
C4 C3 1.369(5) . ?
C4 C5 1.393(5) . ?
C2 C3 1.402(4) . ?
C9 C8 1.512(5) . ?
C8 C10 1.512(4) . ?
C11 C12 1.380(5) . ?
C11 C10 1.388(4) . ?
C10 C15 1.385(5) . ?
C15 C14 1.377(6) . ?
C13 C12 1.353(6) . ?
C13 C14 1.369(7) . ?

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 143.53(13) 2_656 . ?
O1 Cu1 N1 101.75(9) 2_656 2_656 ?
O1 Cu1 N1 92.93(9) . 2_656 ?
O1 Cu1 N1 92.93(9) 2_656 . ?
O1 Cu1 N1 101.75(9) . . ?
N1 Cu1 N1 131.96(14) 2_656 . ?
C5 C6 C7 124.1(3) . . ?
C5 C6 Br1 119.2(2) . . ?
C7 C6 Br1 116.6(2) . . ?
C7 O1 Cu1 127.02(18) . . ?
O1 C7 C6 120.8(3) . . ?
O1 C7 C2 124.1(3) . . ?
C6 C7 C2 115.1(3) . . ?
N1 C1 C2 127.9(3) . 2_656 ?
C1 N1 C8 116.0(2) . . ?
C1 N1 Cu1 120.09(19) . . ?
C8 N1 Cu1 123.27(19) . . ?
C3 C4 C5 120.7(3) . . ?
C3 C4 Cl1 119.9(3) . . ?
C5 C4 Cl1 119.4(3) . . ?
C6 C5 C4 118.6(3) . . ?
C3 C2 C7 121.0(3) . . ?
C3 C2 C1 117.0(3) . 2_656 ?
C7 C2 C1 122.0(3) . 2_656 ?
C4 C3 C2 120.2(3) . . ?
N1 C8 C9 108.8(2) . . ?
N1 C8 C10 109.7(2) . . ?
C9 C8 C10 115.1(3) . . ?
C12 C11 C10 120.2(3) . . ?
C15 C10 C11 117.9(3) . . ?
C15 C10 C8 118.9(3) . . ?
C11 C10 C8 123.2(3) . . ?
C14 C15 C10 121.2(4) . . ?
C12 C13 C14 119.9(4) . . ?
C13 C12 C11 121.0(4) . . ?
C13 C14 C15 119.8(4) . . ?

_refine_diff_density_max         0.405
_refine_diff_density_min         -0.212
_refine_diff_density_rms         0.053

####################################################################### 
# 
# 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_CCDC3
_database_code_depnum_ccdc_archive 'CCDC 1943420'
loop_
_audit_author_name
_audit_author_address
'Hadi Rudbari' 'Isfahan University'
_audit_update_record             
;
2019-07-26 deposited with the CCDC.	2020-06-02 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            'C30 H24 Cu I4 N2 O2'
_chemical_formula_weight         1015.65

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'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_H-M_alt        'C 2'
_space_group_name_Hall           'C 2y'

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

_cell_length_a                   14.5549(3)
_cell_length_b                   11.1475(3)
_cell_length_c                   10.6074(3)
_cell_angle_alpha                90
_cell_angle_beta                 118.1800(10)
_cell_angle_gamma                90
_cell_volume                     1517.06(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9893
_cell_measurement_theta_min      2.42
_cell_measurement_theta_max      34.66

_exptl_crystal_description       flat
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.223
_exptl_crystal_F_000             950
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.09
_exptl_absorpt_coefficient_mu    4.820
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4686
_exptl_absorpt_correction_T_max  0.7468
_exptl_absorpt_process_details   'SADABS; Bruker, 2008'
_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       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            31030
_diffrn_reflns_av_unetI/netI     0.0512
_diffrn_reflns_av_R_equivalents  0.1195
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.178
_diffrn_reflns_theta_max         34.717
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             6381
_reflns_number_gt                5772
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.878
_reflns_Friedel_fraction_max     0.950
_reflns_Friedel_fraction_full    1.000

_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, 2007)'
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_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)+(0.0768P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 2508 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.021(14)
_chemical_absolute_configuration rmad
_refine_ls_number_reflns         6381
_refine_ls_number_parameters     177
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0506
_refine_ls_R_factor_gt           0.0452
_refine_ls_wR_factor_ref         0.1179
_refine_ls_wR_factor_gt          0.1132
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.054
_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
I1 I 0.17918(3) 0.17755(3) 0.11065(4) 0.03364(10) Uani 1 1 d . . . . .
I2 I -0.05134(3) 0.52998(5) 0.28253(5) 0.04683(14) Uani 1 1 d . . . . .
Cu1 Cu 0.500000 0.34986(8) 0.500000 0.02286(16) Uani 1 2 d S T P . .
O1 O 0.3632(3) 0.2964(4) 0.3787(4) 0.0262(7) Uani 1 1 d . . . . .
N1 N 0.4611(3) 0.4266(4) 0.6399(5) 0.0254(7) Uani 1 1 d . . . . .
C7 C 0.2774(3) 0.3369(4) 0.3722(5) 0.0214(7) Uani 1 1 d . . . . .
C10 C 0.6216(5) 0.5445(5) 0.7760(6) 0.0307(10) Uani 1 1 d . . . . .
C1 C 0.3654(4) 0.4559(5) 0.6000(6) 0.0284(9) Uani 1 1 d . . . . .
H1 H 0.354079 0.505843 0.661618 0.034 Uiso 1 1 calc R U . . .
C6 C 0.1796(4) 0.3002(4) 0.2597(5) 0.0244(8) Uani 1 1 d . . . . .
C2 C 0.2741(4) 0.4203(5) 0.4711(5) 0.0252(8) Uani 1 1 d . . . . .
C9 C 0.5775(6) 0.3615(6) 0.8857(6) 0.0384(12) Uani 1 1 d . . . . .
H9A H 0.627147 0.388109 0.979558 0.058 Uiso 1 1 calc R U . . .
H9B H 0.519998 0.323234 0.890168 0.058 Uiso 1 1 calc R U . . .
H9C H 0.610283 0.305381 0.850870 0.058 Uiso 1 1 calc R U . . .
C8 C 0.5378(4) 0.4693(6) 0.7846(5) 0.0291(9) Uani 1 1 d . . . . .
H8 H 0.500392 0.521657 0.819232 0.035 Uiso 1 1 calc R U . . .
C11 C 0.7272(5) 0.5246(6) 0.8604(6) 0.0355(11) Uani 1 1 d . . . . .
H11 H 0.749289 0.460572 0.924142 0.043 Uiso 1 1 calc R U . . .
C13 C 0.7672(8) 0.6953(8) 0.7561(10) 0.061(2) Uani 1 1 d . . . . .
H13 H 0.815927 0.745946 0.750443 0.073 Uiso 1 1 calc R U . . .
C5 C 0.0864(4) 0.3507(5) 0.2384(6) 0.0292(9) Uani 1 1 d . . . . .
H5 H 0.023686 0.325527 0.162578 0.035 Uiso 1 1 calc R U . . .
C3 C 0.1792(4) 0.4716(6) 0.4474(6) 0.0304(10) Uani 1 1 d . . . . .
H3 H 0.178723 0.528159 0.511544 0.036 Uiso 1 1 calc R U . . .
C14 C 0.6647(9) 0.7147(8) 0.6725(11) 0.064(2) Uani 1 1 d . . . . .
H14 H 0.643126 0.777185 0.606683 0.077 Uiso 1 1 calc R U . . .
C12 C 0.8005(7) 0.5982(8) 0.8520(10) 0.0517(19) Uani 1 1 d . . . . .
H12 H 0.871259 0.583539 0.909201 0.062 Uiso 1 1 calc R U . . .
C4 C 0.0872(4) 0.4396(6) 0.3313(6) 0.0306(10) Uani 1 1 d . . . . .
C15 C 0.5907(7) 0.6429(7) 0.6829(9) 0.0490(18) Uani 1 1 d . . . . .
H15 H 0.520185 0.660260 0.627721 0.059 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
I1 C6 2.088(5) . ?
I2 C4 2.089(5) . ?
Cu1 O1 1.885(4) 2_656 ?
Cu1 O1 1.885(4) . ?
Cu1 N1 2.012(4) . ?
Cu1 N1 2.012(4) 2_656 ?
O1 C7 1.299(6) . ?
N1 C1 1.292(7) . ?
N1 C8 1.487(6) . ?
C7 C6 1.419(6) . ?
C7 C2 1.420(7) . ?
C10 C11 1.384(8) . ?
C10 C15 1.401(9) . ?
C10 C8 1.518(9) . ?
C1 C2 1.441(7) . ?
C1 H1 0.9300 . ?
C6 C5 1.386(7) . ?
C2 C3 1.403(7) . ?
C9 C8 1.531(9) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C8 H8 0.9800 . ?
C11 C12 1.382(11) . ?
C11 H11 0.9300 . ?
C13 C14 1.345(15) . ?
C13 C12 1.405(14) . ?
C13 H13 0.9300 . ?
C5 C4 1.393(8) . ?
C5 H5 0.9300 . ?
C3 C4 1.371(8) . ?
C3 H3 0.9300 . ?
C14 C15 1.388(13) . ?
C14 H14 0.9300 . ?
C12 H12 0.9300 . ?
C15 H15 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Cu1 O1 143.1(3) 2_656 . ?
O1 Cu1 N1 101.86(18) 2_656 . ?
O1 Cu1 N1 93.63(17) . . ?
O1 Cu1 N1 93.63(17) 2_656 2_656 ?
O1 Cu1 N1 101.86(17) . 2_656 ?
N1 Cu1 N1 129.7(3) . 2_656 ?
C7 O1 Cu1 127.2(3) . . ?
C1 N1 C8 115.1(5) . . ?
C1 N1 Cu1 120.1(4) . . ?
C8 N1 Cu1 124.2(4) . . ?
O1 C7 C6 120.1(4) . . ?
O1 C7 C2 123.8(4) . . ?
C6 C7 C2 116.1(4) . . ?
C11 C10 C15 118.1(6) . . ?
C11 C10 C8 123.4(6) . . ?
C15 C10 C8 118.4(6) . . ?
N1 C1 C2 127.5(5) . . ?
N1 C1 H1 116.2 . . ?
C2 C1 H1 116.2 . . ?
C5 C6 C7 122.4(4) . . ?
C5 C6 I1 119.4(4) . . ?
C7 C6 I1 117.9(3) . . ?
C3 C2 C7 120.6(5) . . ?
C3 C2 C1 116.5(5) . . ?
C7 C2 C1 122.9(4) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N1 C8 C10 110.3(5) . . ?
N1 C8 C9 108.8(5) . . ?
C10 C8 C9 115.3(5) . . ?
N1 C8 H8 107.3 . . ?
C10 C8 H8 107.3 . . ?
C9 C8 H8 107.3 . . ?
C12 C11 C10 121.3(7) . . ?
C12 C11 H11 119.4 . . ?
C10 C11 H11 119.4 . . ?
C14 C13 C12 119.8(8) . . ?
C14 C13 H13 120.1 . . ?
C12 C13 H13 120.1 . . ?
C6 C5 C4 119.6(5) . . ?
C6 C5 H5 120.2 . . ?
C4 C5 H5 120.2 . . ?
C4 C3 C2 121.1(5) . . ?
C4 C3 H3 119.5 . . ?
C2 C3 H3 119.5 . . ?
C13 C14 C15 121.1(9) . . ?
C13 C14 H14 119.4 . . ?
C15 C14 H14 119.4 . . ?
C11 C12 C13 119.4(8) . . ?
C11 C12 H12 120.3 . . ?
C13 C12 H12 120.3 . . ?
C3 C4 C5 119.9(5) . . ?
C3 C4 I2 121.1(4) . . ?
C5 C4 I2 118.9(4) . . ?
C14 C15 C10 120.3(8) . . ?
C14 C15 H15 119.9 . . ?
C10 C15 H15 119.9 . . ?

_refine_diff_density_max         3.719
_refine_diff_density_min         -1.722
_refine_diff_density_rms         0.295

####################################################################### 
# 
# 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_gb7
_database_code_depnum_ccdc_archive 'CCDC 1943418'
loop_
_audit_author_name
_audit_author_address
'Hadi Rudbari' 'Isfahan University'
_audit_update_record             
;
2019-07-26 deposited with the CCDC.	2020-06-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C30 H24 Cl4 Cu N2 O2'
_chemical_formula_sum            'C30 H24 Cl4 Cu N2 O2'
_chemical_formula_weight         649.85

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu -1.9646 0.5888 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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'

_cell_length_a                   8.57142(6)
_cell_length_b                   14.70541(11)
_cell_length_c                   11.09232(8)
_cell_angle_alpha                90
_cell_angle_beta                 97.2834(7)
_cell_angle_gamma                90
_cell_volume                     1386.863(18)
_cell_formula_units_Z            2
_cell_measurement_temperature    140.01(10)
_cell_measurement_reflns_used    8501
_cell_measurement_theta_min      3.9980
_cell_measurement_theta_max      75.8270

_exptl_crystal_description       prism
_exptl_crystal_colour            'dark black'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.556
_exptl_crystal_F_000             662
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.543
_exptl_crystal_size_mid          0.247
_exptl_crystal_size_min          0.175
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
5 0 -2 0.2429
0 10 0 0.1145
-5 4 2 0.2878
-5 -1 2 0.2720
0 -10 0 0.1215
0 5 -6 0.0807
5 1 1 0.2536
0 -5 6 0.0979
-5 -3 2 0.2542
-5 0 -1 0.2614
5 2 -4 0.2196
4 1 -5 0.1992
0 -9 -3 0.1177
-5 0 4 0.2653
0 -3 -7 0.1039
0 3 7 0.1048
4 4 4 0.2233
0 4 -7 0.0766
4 0 -5 0.2029
0 5 -6 0.0758
0 8 -4 0.0941
0 6 6 0.1065
_exptl_absorpt_coefficient_mu    4.917
_shelx_estimated_absorpt_T_min   0.175
_shelx_estimated_absorpt_T_max   0.480
_exptl_absorpt_correction_T_min  0.31799
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      140.01(10)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            AtlasS2
_diffrn_detector_area_resol_mean 5.2817
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -64.00  32.00   1.00    1.00    --  -40.91  57.00   0.00   96
  2  ω    -32.00  -5.00   1.00    1.00    --  -40.91 125.00  30.00   27
  3  ω      5.00  54.00   1.00    1.00    --   40.91 -99.00  90.00   49
  4  ω     39.00 134.00   1.00    4.00    --  111.85 -45.00 -60.00   95
  5  ω     85.00 178.00   1.00    4.00    --  111.85  30.00  30.00   93
  6  ω    101.00 139.00   1.00    4.00    --  111.85 125.00 -60.00   38
  7  ω     85.00 178.00   1.00    4.00    --  111.85  30.00 120.00   93
  8  ω     66.00 109.00   1.00    4.00    --  111.85 -94.00 150.00   43
  9  ω     53.00 108.00   1.00    4.00    --  111.85 -94.00  60.00   55
 10  ω     70.00 141.00   1.00    4.00    --  111.85 -61.00  30.00   71
 11  ω     63.00  93.00   1.00    4.00    --  111.85 -94.00-120.00   30
 12  ω     36.00 109.00   1.00    4.00    --  111.85 -30.00-150.00   73
 13  ω     55.00  96.00   1.00    1.00    --   40.91-125.00-150.00   41
 14  ω     47.00 110.00   1.00    4.00    --  111.85-100.00 -41.00   63
 15  ω     43.00 118.00   1.00    4.00    --  111.85 -45.00 150.00   75
 16  ω    -85.00 -59.00   1.00    1.00    --  -40.91 125.00  30.00   26
 17  ω   -115.00 -16.00   1.00    1.00    --  -40.91 -38.00 120.00   99
 18  ω   -111.00 -26.00   1.00    1.00    --  -40.91 -38.00-150.00   85
;
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_number            9280
_diffrn_reflns_av_unetI/netI     0.0174
_diffrn_reflns_av_R_equivalents  0.0143
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         4.018
_diffrn_reflns_theta_max         76.011
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.859
_diffrn_reflns_point_group_measured_fraction_full 0.896
_reflns_number_total             4988
_reflns_number_gt                4980
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.692
_reflns_Friedel_fraction_max     0.732
_reflns_Friedel_fraction_full    0.782

_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       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Mercury 4.1.0 (CCDC, 2019)'
_computing_publication_material  'CIFTab (Sheldrick, 2015)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0509P)²+0.2627P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.0033(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   0.010(11)
_chemical_absolute_configuration rmad
_refine_ls_number_reflns         4988
_refine_ls_number_parameters     355
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0251
_refine_ls_R_factor_gt           0.0251
_refine_ls_wR_factor_ref         0.0655
_refine_ls_wR_factor_gt          0.0655
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.043
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.31455(4) 0.57904(2) 0.42933(3) 0.01059(11) Uani 1 1 d . . . . .
Cl1 Cl -0.02702(8) 0.68572(4) 0.09470(6) 0.02101(15) Uani 1 1 d . . . . .
Cl2 Cl -0.26487(9) 0.34774(6) 0.02795(7) 0.03194(19) Uani 1 1 d . . . . .
Cl3 Cl 0.55722(7) 0.61243(5) 0.83138(5) 0.02034(15) Uani 1 1 d . . . . .
Cl4 Cl 1.12587(6) 0.65025(4) 0.67739(6) 0.01807(14) Uani 1 1 d . . . . .
O1 O 0.1364(2) 0.61086(13) 0.31767(16) 0.0134(3) Uani 1 1 d . . . . .
O2 O 0.44497(19) 0.59542(13) 0.57740(15) 0.0130(4) Uani 1 1 d . . . . .
N1 N 0.2049(2) 0.47027(15) 0.48695(18) 0.0120(4) Uani 1 1 d . . . . .
N2 N 0.4767(2) 0.62256(15) 0.33012(18) 0.0113(4) Uani 1 1 d . . . . .
C1 C 0.0925(3) 0.43090(18) 0.4196(2) 0.0153(5) Uani 1 1 d . . . . .
H1 H 0.054990 0.375378 0.448971 0.018 Uiso 1 1 calc R U . . .
C2 C 0.0170(3) 0.46282(19) 0.3029(2) 0.0148(5) Uani 1 1 d . . . . .
C3 C -0.0805(3) 0.4008(2) 0.2323(2) 0.0189(5) Uani 1 1 d . . . . .
H3 H -0.095041 0.341214 0.261928 0.023 Uiso 1 1 calc R U . . .
C4 C -0.1550(3) 0.4267(2) 0.1201(3) 0.0196(6) Uani 1 1 d . . . . .
C5 C -0.1422(3) 0.5148(2) 0.0781(2) 0.0183(5) Uani 1 1 d . . . . .
H5 H -0.198167 0.532980 0.002530 0.022 Uiso 1 1 calc R U . . .
C6 C -0.0472(3) 0.5757(2) 0.1475(2) 0.0147(4) Uani 1 1 d . . . . .
C7 C 0.0421(3) 0.55200(18) 0.2602(2) 0.0124(5) Uani 1 1 d . . . . .
C8 C 0.2738(3) 0.42823(17) 0.6032(2) 0.0131(5) Uani 1 1 d . . . . .
H8 H 0.294726 0.478531 0.663795 0.016 Uiso 1 1 calc R U . . .
C9 C 0.1662(3) 0.3599(2) 0.6561(2) 0.0174(5) Uani 1 1 d . . . . .
H9A H 0.215602 0.339841 0.736251 0.026 Uiso 1 1 calc R U . . .
H9B H 0.149131 0.307270 0.601854 0.026 Uiso 1 1 calc R U . . .
H9C H 0.065041 0.388792 0.664184 0.026 Uiso 1 1 calc R U . . .
C10 C 0.4320(3) 0.38656(18) 0.5864(2) 0.0141(5) Uani 1 1 d . . . . .
C11 C 0.5525(3) 0.3872(2) 0.6843(3) 0.0191(5) Uani 1 1 d . . . . .
H11 H 0.535097 0.414621 0.758988 0.023 Uiso 1 1 calc R U . . .
C12 C 0.6972(3) 0.3479(2) 0.6728(3) 0.0236(6) Uani 1 1 d . . . . .
H12 H 0.777586 0.347549 0.740121 0.028 Uiso 1 1 calc R U . . .
C13 C 0.7252(3) 0.3089(2) 0.5627(3) 0.0244(6) Uani 1 1 d . . . . .
H13 H 0.824591 0.282610 0.554698 0.029 Uiso 1 1 calc R U . . .
C14 C 0.6067(4) 0.3090(2) 0.4652(3) 0.0230(6) Uani 1 1 d . . . . .
H14 H 0.625270 0.283231 0.389759 0.028 Uiso 1 1 calc R U . . .
C15 C 0.4608(3) 0.34667(19) 0.4775(2) 0.0178(5) Uani 1 1 d . . . . .
H15 H 0.379584 0.345179 0.410755 0.021 Uiso 1 1 calc R U . . .
C16 C 0.6229(3) 0.63005(18) 0.3720(2) 0.0129(5) Uani 1 1 d . . . . .
H16 H 0.694096 0.641275 0.314712 0.016 Uiso 1 1 calc R U . . .
C17 C 0.6895(3) 0.62299(18) 0.4987(2) 0.0123(5) Uani 1 1 d . . . . .
C18 C 0.8534(3) 0.63423(18) 0.5252(2) 0.0133(5) Uani 1 1 d . . . . .
H18 H 0.916490 0.638963 0.460975 0.016 Uiso 1 1 calc R U . . .
C19 C 0.9223(3) 0.63838(18) 0.6440(2) 0.0141(5) Uani 1 1 d . . . . .
C20 C 0.8324(3) 0.63279(19) 0.7403(2) 0.0148(5) Uani 1 1 d . . . . .
H20 H 0.880372 0.637901 0.822016 0.018 Uiso 1 1 calc R U . . .
C21 C 0.6719(3) 0.61967(19) 0.7139(2) 0.0146(5) Uani 1 1 d . . . . .
C22 C 0.5944(3) 0.61125(18) 0.5936(2) 0.0113(4) Uani 1 1 d . . . . .
C23 C 0.4254(3) 0.63785(18) 0.1986(2) 0.0118(5) Uani 1 1 d . . . . .
H23 H 0.328273 0.676121 0.193223 0.014 Uiso 1 1 calc R U . . .
C24 C 0.5422(3) 0.68937(19) 0.1314(2) 0.0161(5) Uani 1 1 d . . . . .
H24A H 0.492302 0.705064 0.049644 0.024 Uiso 1 1 calc R U . . .
H24B H 0.634408 0.651062 0.125412 0.024 Uiso 1 1 calc R U . . .
H24C H 0.574913 0.745134 0.175988 0.024 Uiso 1 1 calc R U . . .
C25 C 0.3769(3) 0.54794(19) 0.1367(2) 0.0150(5) Uani 1 1 d . . . . .
C26 C 0.2829(3) 0.5514(2) 0.0242(3) 0.0237(6) Uani 1 1 d . . . . .
H26 H 0.253884 0.608571 -0.011837 0.028 Uiso 1 1 calc R U . . .
C27 C 0.2317(4) 0.4712(3) -0.0351(3) 0.0325(8) Uani 1 1 d . . . . .
H27 H 0.168332 0.473731 -0.111742 0.039 Uiso 1 1 calc R U . . .
C28 C 0.2730(5) 0.3886(3) 0.0173(4) 0.0387(9) Uani 1 1 d . . . . .
H28 H 0.235970 0.334121 -0.022474 0.046 Uiso 1 1 calc R U . . .
C29 C 0.3680(5) 0.3843(2) 0.1273(3) 0.0368(8) Uani 1 1 d . . . . .
H29 H 0.397147 0.326970 0.162565 0.044 Uiso 1 1 calc R U . . .
C30 C 0.4212(4) 0.4643(2) 0.1869(3) 0.0254(6) Uani 1 1 d . . . . .
H30 H 0.487855 0.461166 0.262013 0.030 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 O2 1.8814(17) . ?
Cu1 O1 1.8988(18) . ?
Cu1 N2 1.985(2) . ?
Cu1 N1 2.001(2) . ?
Cl1 C6 1.737(3) . ?
Cl2 C4 1.742(3) . ?
Cl3 C21 1.732(2) . ?
Cl4 C19 1.746(2) . ?
O1 C7 1.296(3) . ?
O2 C22 1.291(3) . ?
N1 C1 1.280(4) . ?
N1 C8 1.484(3) . ?
N2 C16 1.284(3) . ?
N2 C23 1.486(3) . ?
C1 C2 1.450(3) . ?
C2 C3 1.406(4) . ?
C2 C7 1.420(4) . ?
C3 C4 1.379(4) . ?
C4 C5 1.386(4) . ?
C5 C6 1.378(4) . ?
C6 C7 1.424(3) . ?
C8 C10 1.521(3) . ?
C8 C9 1.530(4) . ?
C10 C15 1.393(4) . ?
C10 C11 1.400(4) . ?
C11 C12 1.389(4) . ?
C12 C13 1.397(5) . ?
C13 C14 1.387(4) . ?
C14 C15 1.391(4) . ?
C16 C17 1.452(3) . ?
C17 C18 1.408(3) . ?
C17 C22 1.421(3) . ?
C18 C19 1.376(3) . ?
C19 C20 1.396(4) . ?
C20 C21 1.383(4) . ?
C21 C22 1.419(3) . ?
C23 C25 1.523(4) . ?
C23 C24 1.523(3) . ?
C25 C30 1.384(4) . ?
C25 C26 1.398(4) . ?
C26 C27 1.394(5) . ?
C27 C28 1.373(6) . ?
C28 C29 1.380(6) . ?
C29 C30 1.396(5) . ?

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 O1 151.36(8) . . ?
O2 Cu1 N2 93.57(8) . . ?
O1 Cu1 N2 96.93(8) . . ?
O2 Cu1 N1 94.29(8) . . ?
O1 Cu1 N1 91.94(8) . . ?
N2 Cu1 N1 145.61(9) . . ?
C7 O1 Cu1 123.81(17) . . ?
C22 O2 Cu1 127.87(15) . . ?
C1 N1 C8 120.4(2) . . ?
C1 N1 Cu1 121.64(18) . . ?
C8 N1 Cu1 117.35(16) . . ?
C16 N2 C23 119.7(2) . . ?
C16 N2 Cu1 123.12(17) . . ?
C23 N2 Cu1 116.85(15) . . ?
N1 C1 C2 126.3(2) . . ?
C3 C2 C7 121.1(2) . . ?
C3 C2 C1 117.0(2) . . ?
C7 C2 C1 121.8(2) . . ?
C4 C3 C2 119.9(3) . . ?
C3 C4 C5 120.9(3) . . ?
C3 C4 Cl2 120.0(2) . . ?
C5 C4 Cl2 119.1(2) . . ?
C6 C5 C4 119.1(2) . . ?
C5 C6 C7 123.0(3) . . ?
C5 C6 Cl1 119.6(2) . . ?
C7 C6 Cl1 117.3(2) . . ?
O1 C7 C2 124.3(2) . . ?
O1 C7 C6 120.0(2) . . ?
C2 C7 C6 115.6(2) . . ?
N1 C8 C10 108.9(2) . . ?
N1 C8 C9 114.5(2) . . ?
C10 C8 C9 111.9(2) . . ?
C15 C10 C11 118.8(2) . . ?
C15 C10 C8 122.3(2) . . ?
C11 C10 C8 118.9(2) . . ?
C12 C11 C10 120.4(3) . . ?
C11 C12 C13 120.4(3) . . ?
C14 C13 C12 119.4(3) . . ?
C13 C14 C15 120.2(3) . . ?
C14 C15 C10 120.9(3) . . ?
N2 C16 C17 126.1(2) . . ?
C18 C17 C22 120.7(2) . . ?
C18 C17 C16 116.9(2) . . ?
C22 C17 C16 122.2(2) . . ?
C19 C18 C17 120.0(2) . . ?
C18 C19 C20 121.2(2) . . ?
C18 C19 Cl4 120.2(2) . . ?
C20 C19 Cl4 118.53(19) . . ?
C21 C20 C19 118.5(2) . . ?
C20 C21 C22 123.1(2) . . ?
C20 C21 Cl3 119.60(19) . . ?
C22 C21 Cl3 117.32(19) . . ?
O2 C22 C21 119.0(2) . . ?
O2 C22 C17 124.8(2) . . ?
C21 C22 C17 116.2(2) . . ?
N2 C23 C25 109.9(2) . . ?
N2 C23 C24 115.1(2) . . ?
C25 C23 C24 111.7(2) . . ?
C30 C25 C26 119.3(3) . . ?
C30 C25 C23 123.1(2) . . ?
C26 C25 C23 117.6(2) . . ?
C27 C26 C25 120.1(3) . . ?
C28 C27 C26 120.0(3) . . ?
C27 C28 C29 120.4(3) . . ?
C28 C29 C30 120.1(4) . . ?
C25 C30 C29 120.1(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
O2 Cu1 O1 C7 -137.02(19) . . . . ?
N2 Cu1 O1 C7 112.29(19) . . . . ?
N1 Cu1 O1 C7 -34.42(19) . . . . ?
O1 Cu1 O2 C22 -123.5(2) . . . . ?
N2 Cu1 O2 C22 -12.0(2) . . . . ?
N1 Cu1 O2 C22 134.5(2) . . . . ?
C8 N1 C1 C2 -178.4(2) . . . . ?
Cu1 N1 C1 C2 -7.6(4) . . . . ?
N1 C1 C2 C3 167.0(3) . . . . ?
N1 C1 C2 C7 -11.8(4) . . . . ?
C7 C2 C3 C4 -0.7(4) . . . . ?
C1 C2 C3 C4 -179.6(3) . . . . ?
C2 C3 C4 C5 -3.5(4) . . . . ?
C2 C3 C4 Cl2 175.6(2) . . . . ?
C3 C4 C5 C6 3.2(4) . . . . ?
Cl2 C4 C5 C6 -175.9(2) . . . . ?
C4 C5 C6 C7 1.4(4) . . . . ?
C4 C5 C6 Cl1 178.7(2) . . . . ?
Cu1 O1 C7 C2 26.1(3) . . . . ?
Cu1 O1 C7 C6 -155.18(18) . . . . ?
C3 C2 C7 O1 -176.3(2) . . . . ?
C1 C2 C7 O1 2.5(4) . . . . ?
C3 C2 C7 C6 4.9(4) . . . . ?
C1 C2 C7 C6 -176.3(2) . . . . ?
C5 C6 C7 O1 175.9(2) . . . . ?
Cl1 C6 C7 O1 -1.5(3) . . . . ?
C5 C6 C7 C2 -5.3(4) . . . . ?
Cl1 C6 C7 C2 177.29(18) . . . . ?
C1 N1 C8 C10 104.1(3) . . . . ?
Cu1 N1 C8 C10 -67.0(2) . . . . ?
C1 N1 C8 C9 -21.9(3) . . . . ?
Cu1 N1 C8 C9 166.95(17) . . . . ?
N1 C8 C10 C15 -34.7(3) . . . . ?
C9 C8 C10 C15 92.8(3) . . . . ?
N1 C8 C10 C11 146.1(2) . . . . ?
C9 C8 C10 C11 -86.3(3) . . . . ?
C15 C10 C11 C12 -0.6(4) . . . . ?
C8 C10 C11 C12 178.6(3) . . . . ?
C10 C11 C12 C13 1.3(5) . . . . ?
C11 C12 C13 C14 -0.6(5) . . . . ?
C12 C13 C14 C15 -0.7(5) . . . . ?
C13 C14 C15 C10 1.4(4) . . . . ?
C11 C10 C15 C14 -0.7(4) . . . . ?
C8 C10 C15 C14 -179.9(3) . . . . ?
C23 N2 C16 C17 175.8(2) . . . . ?
Cu1 N2 C16 C17 -10.5(4) . . . . ?
N2 C16 C17 C18 -179.4(3) . . . . ?
N2 C16 C17 C22 -3.5(4) . . . . ?
C22 C17 C18 C19 -3.2(4) . . . . ?
C16 C17 C18 C19 172.9(2) . . . . ?
C17 C18 C19 C20 -0.8(4) . . . . ?
C17 C18 C19 Cl4 178.8(2) . . . . ?
C18 C19 C20 C21 2.3(4) . . . . ?
Cl4 C19 C20 C21 -177.4(2) . . . . ?
C19 C20 C21 C22 0.2(4) . . . . ?
C19 C20 C21 Cl3 180.0(2) . . . . ?
Cu1 O2 C22 C21 -178.70(18) . . . . ?
Cu1 O2 C22 C17 2.6(4) . . . . ?
C20 C21 C22 O2 177.2(3) . . . . ?
Cl3 C21 C22 O2 -2.5(3) . . . . ?
C20 C21 C22 C17 -4.0(4) . . . . ?
Cl3 C21 C22 C17 176.3(2) . . . . ?
C18 C17 C22 O2 -175.9(2) . . . . ?
C16 C17 C22 O2 8.3(4) . . . . ?
C18 C17 C22 C21 5.4(4) . . . . ?
C16 C17 C22 C21 -170.4(2) . . . . ?
C16 N2 C23 C25 109.0(3) . . . . ?
Cu1 N2 C23 C25 -65.0(2) . . . . ?
C16 N2 C23 C24 -18.1(3) . . . . ?
Cu1 N2 C23 C24 167.81(17) . . . . ?
N2 C23 C25 C30 -18.4(3) . . . . ?
C24 C23 C25 C30 110.6(3) . . . . ?
N2 C23 C25 C26 161.3(2) . . . . ?
C24 C23 C25 C26 -69.7(3) . . . . ?
C30 C25 C26 C27 1.4(4) . . . . ?
C23 C25 C26 C27 -178.4(3) . . . . ?
C25 C26 C27 C28 0.3(5) . . . . ?
C26 C27 C28 C29 -1.4(5) . . . . ?
C27 C28 C29 C30 0.8(5) . . . . ?
C26 C25 C30 C29 -2.1(4) . . . . ?
C23 C25 C30 C29 177.7(3) . . . . ?
C28 C29 C30 C25 1.0(5) . . . . ?

_refine_diff_density_max         0.316
_refine_diff_density_min         -0.377
_refine_diff_density_rms         0.051

####################################################################### 
# 
# 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_CCDC4
_database_code_depnum_ccdc_archive 'CCDC 1943414'
loop_
_audit_author_name
_audit_author_address
'Hadi Rudbari' 'Isfahan University'
_audit_update_record             
;
2019-07-26 deposited with the CCDC.	2020-06-02 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            'C30 H24 Cu I4 N2 O2'
_chemical_formula_weight         1015.65

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'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_H-M_alt        'C 2'
_space_group_name_Hall           'C 2y'

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

_cell_length_a                   14.5586(3)
_cell_length_b                   11.1467(2)
_cell_length_c                   10.6165(2)
_cell_angle_alpha                90
_cell_angle_beta                 118.2090(10)
_cell_angle_gamma                90
_cell_volume                     1518.22(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    9868
_cell_measurement_theta_min      2.42
_cell_measurement_theta_max      40.13

_exptl_crystal_description       irregular
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.222
_exptl_crystal_F_000             950
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.13
_exptl_absorpt_coefficient_mu    4.817
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.449
_exptl_absorpt_correction_T_max  0.617
_exptl_absorpt_process_details   'SADABS; Bruker, 2008'
_diffrn_ambient_temperature      273(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            39452
_diffrn_reflns_av_unetI/netI     0.0256
_diffrn_reflns_av_R_equivalents  0.0269
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.420
_diffrn_reflns_theta_max         42.233
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             10671
_reflns_number_gt                9091
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.931
_reflns_Friedel_fraction_max     0.997
_reflns_Friedel_fraction_full    1.000

_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, 2007)'
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0459P)²+0.3211P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.022(18)
_chemical_absolute_configuration rmad
_refine_ls_number_reflns         10671
_refine_ls_number_parameters     178
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0418
_refine_ls_R_factor_gt           0.0329
_refine_ls_wR_factor_ref         0.0844
_refine_ls_wR_factor_gt          0.0801
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_restrained_S_all      1.063
_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
I1 I 0.82088(2) 1.00685(2) 0.88914(2) 0.03469(5) Uani 1 1 d . . . . .
I2 I 1.05125(2) 0.65438(3) 0.71734(3) 0.04829(8) Uani 1 1 d . . . . .
Cu1 Cu 0.500000 0.83453(5) 0.500000 0.02403(8) Uani 1 2 d S T P . .
C1 C 0.6345(2) 0.7285(3) 0.3995(3) 0.0282(5) Uani 1 1 d . . . . .
H1 H 0.645900 0.678551 0.338082 0.034 Uiso 1 1 calc R U . . .
N1 N 0.53917(19) 0.7578(2) 0.3598(3) 0.0265(4) Uani 1 1 d . . . . .
O1 O 0.63681(15) 0.8879(2) 0.6211(2) 0.0277(4) Uani 1 1 d . . . . .
C2 C 0.7256(2) 0.7644(3) 0.5286(3) 0.0260(4) Uani 1 1 d . . . . .
C7 C 0.72237(17) 0.8471(2) 0.6280(3) 0.0227(4) Uani 1 1 d . . . . .
C4 C 0.9131(2) 0.7451(3) 0.6687(3) 0.0315(5) Uani 1 1 d . . . . .
C3 C 0.8209(2) 0.7128(3) 0.5521(3) 0.0315(5) Uani 1 1 d . . . . .
H3 H 0.821353 0.656320 0.487974 0.038 Uiso 1 1 calc R U . . .
C6 C 0.82011(19) 0.8840(3) 0.7399(3) 0.0255(4) Uani 1 1 d . . . . .
C10 C 0.3785(2) 0.6403(3) 0.2243(3) 0.0315(5) Uani 1 1 d . . . . .
C5 C 0.91359(19) 0.8340(3) 0.7621(3) 0.0302(5) Uani 1 1 d . . . . .
H5 H 0.976071 0.859323 0.838214 0.036 Uiso 1 1 calc R U . . .
C15 C 0.4098(5) 0.5419(4) 0.3177(6) 0.0517(11) Uani 1 1 d . . . . .
H15 H 0.480267 0.524522 0.372428 0.062 Uiso 1 1 calc R U . . .
C8 C 0.4617(2) 0.7156(3) 0.2146(3) 0.0304(5) Uani 1 1 d . . . . .
H8 H 0.498764 0.663087 0.179641 0.036 Uiso 1 1 calc R U . . .
C11 C 0.2727(3) 0.6592(4) 0.1394(4) 0.0379(6) Uani 1 1 d . . . . .
H11 H 0.250354 0.722906 0.075215 0.045 Uiso 1 1 calc R U . . .
C13 C 0.2321(5) 0.4907(5) 0.2435(7) 0.0648(15) Uani 1 1 d . . . . .
H13 H 0.183100 0.440791 0.249539 0.078 Uiso 1 1 calc R U . . .
C12 C 0.1994(4) 0.5851(5) 0.1481(6) 0.0520(11) Uani 1 1 d . . . . .
H12 H 0.128618 0.598885 0.089927 0.062 Uiso 1 1 calc R U . . .
C14 C 0.3355(6) 0.4701(5) 0.3288(7) 0.0664(15) Uani 1 1 d . . . . .
H14 H 0.356792 0.407799 0.394932 0.080 Uiso 1 1 calc R U . . .
C9 C 0.4225(3) 0.8225(4) 0.1146(4) 0.0399(7) Uani 1 1 d . . . . .
H9A H 0.372589 0.796029 0.020930 0.060 Uiso 1 1 calc R U . . .
H9B H 0.390113 0.878807 0.149773 0.060 Uiso 1 1 calc R U . . .
H9C H 0.480035 0.860412 0.109964 0.060 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
I1 C6 2.090(3) . ?
I2 C4 2.086(3) . ?
Cu1 O1 1.885(2) . ?
Cu1 O1 1.885(2) 2_656 ?
Cu1 N1 2.018(2) 2_656 ?
Cu1 N1 2.019(2) . ?
C1 N1 1.288(4) . ?
C1 C2 1.442(4) . ?
C1 H1 0.9300 . ?
N1 C8 1.492(4) . ?
O1 C7 1.295(3) . ?
C2 C3 1.411(4) . ?
C2 C7 1.418(4) . ?
C7 C6 1.417(3) . ?
C4 C3 1.376(4) . ?
C4 C5 1.400(4) . ?
C3 H3 0.9300 . ?
C6 C5 1.384(4) . ?
C10 C11 1.384(5) . ?
C10 C15 1.403(6) . ?
C10 C8 1.516(5) . ?
C5 H5 0.9300 . ?
C15 C14 1.394(8) . ?
C15 H15 0.9300 . ?
C8 C9 1.517(5) . ?
C8 H8 0.9800 . ?
C11 C12 1.387(6) . ?
C11 H11 0.9300 . ?
C13 C14 1.361(9) . ?
C13 C12 1.380(9) . ?
C13 H13 0.9300 . ?
C12 H12 0.9300 . ?
C14 H14 0.9300 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Cu1 O1 143.18(15) . 2_656 ?
O1 Cu1 N1 101.92(10) . 2_656 ?
O1 Cu1 N1 93.50(9) 2_656 2_656 ?
O1 Cu1 N1 93.50(9) . . ?
O1 Cu1 N1 101.92(10) 2_656 . ?
N1 Cu1 N1 129.86(16) 2_656 . ?
N1 C1 C2 127.3(3) . . ?
N1 C1 H1 116.4 . . ?
C2 C1 H1 116.4 . . ?
C1 N1 C8 115.4(2) . . ?
C1 N1 Cu1 120.2(2) . . ?
C8 N1 Cu1 123.81(19) . . ?
C7 O1 Cu1 127.25(18) . . ?
C3 C2 C7 120.6(3) . . ?
C3 C2 C1 116.1(2) . . ?
C7 C2 C1 123.3(2) . . ?
O1 C7 C6 120.2(2) . . ?
O1 C7 C2 123.7(2) . . ?
C6 C7 C2 116.0(2) . . ?
C3 C4 C5 119.9(2) . . ?
C3 C4 I2 120.9(2) . . ?
C5 C4 I2 119.1(2) . . ?
C4 C3 C2 120.8(3) . . ?
C4 C3 H3 119.6 . . ?
C2 C3 H3 119.6 . . ?
C5 C6 C7 122.9(2) . . ?
C5 C6 I1 118.8(2) . . ?
C7 C6 I1 117.97(17) . . ?
C11 C10 C15 118.0(4) . . ?
C11 C10 C8 123.4(3) . . ?
C15 C10 C8 118.5(4) . . ?
C6 C5 C4 119.3(3) . . ?
C6 C5 H5 120.4 . . ?
C4 C5 H5 120.4 . . ?
C14 C15 C10 120.2(5) . . ?
C14 C15 H15 119.9 . . ?
C10 C15 H15 119.9 . . ?
N1 C8 C10 110.0(3) . . ?
N1 C8 C9 109.0(3) . . ?
C10 C8 C9 115.7(3) . . ?
N1 C8 H8 107.3 . . ?
C10 C8 H8 107.3 . . ?
C9 C8 H8 107.3 . . ?
C10 C11 C12 121.4(5) . . ?
C10 C11 H11 119.3 . . ?
C12 C11 H11 119.3 . . ?
C14 C13 C12 120.4(5) . . ?
C14 C13 H13 119.8 . . ?
C12 C13 H13 119.8 . . ?
C13 C12 C11 119.6(5) . . ?
C13 C12 H12 120.2 . . ?
C11 C12 H12 120.2 . . ?
C13 C14 C15 120.3(5) . . ?
C13 C14 H14 119.8 . . ?
C15 C14 H14 119.8 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2 C1 N1 C8 175.0(3) . . . . ?
C2 C1 N1 Cu1 -13.3(5) . . . . ?
O1 Cu1 O1 C7 -135.9(3) 2_656 . . . ?
N1 Cu1 O1 C7 111.3(3) 2_656 . . . ?
N1 Cu1 O1 C7 -20.7(3) . . . . ?
N1 C1 C2 C3 175.6(3) . . . . ?
N1 C1 C2 C7 -4.7(5) . . . . ?
Cu1 O1 C7 C6 -170.1(2) . . . . ?
Cu1 O1 C7 C2 9.5(4) . . . . ?
C3 C2 C7 O1 -172.4(3) . . . . ?
C1 C2 C7 O1 7.9(5) . . . . ?
C3 C2 C7 C6 7.2(4) . . . . ?
C1 C2 C7 C6 -172.5(3) . . . . ?
C5 C4 C3 C2 -2.9(5) . . . . ?
I2 C4 C3 C2 172.5(3) . . . . ?
C7 C2 C3 C4 -2.6(5) . . . . ?
C1 C2 C3 C4 177.1(3) . . . . ?
O1 C7 C6 C5 172.8(3) . . . . ?
C2 C7 C6 C5 -6.8(4) . . . . ?
O1 C7 C6 I1 -0.9(4) . . . . ?
C2 C7 C6 I1 179.5(2) . . . . ?
C7 C6 C5 C4 1.6(5) . . . . ?
I1 C6 C5 C4 175.3(3) . . . . ?
C3 C4 C5 C6 3.4(5) . . . . ?
I2 C4 C5 C6 -172.1(3) . . . . ?
C11 C10 C15 C14 -3.4(7) . . . . ?
C8 C10 C15 C14 -179.5(5) . . . . ?
C1 N1 C8 C10 123.0(3) . . . . ?
Cu1 N1 C8 C10 -48.3(4) . . . . ?
C1 N1 C8 C9 -109.1(3) . . . . ?
Cu1 N1 C8 C9 79.6(3) . . . . ?
C11 C10 C8 N1 129.8(3) . . . . ?
C15 C10 C8 N1 -54.3(4) . . . . ?
C11 C10 C8 C9 5.7(5) . . . . ?
C15 C10 C8 C9 -178.4(3) . . . . ?
C15 C10 C11 C12 1.4(6) . . . . ?
C8 C10 C11 C12 177.4(4) . . . . ?
C14 C13 C12 C11 0.0(9) . . . . ?
C10 C11 C12 C13 0.2(7) . . . . ?
C12 C13 C14 C15 -2.0(10) . . . . ?
C10 C15 C14 C13 3.7(10) . . . . ?

_refine_diff_density_max         1.915
_refine_diff_density_min         -0.827
_refine_diff_density_rms         0.209

####################################################################### 
# 
# 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_CCDC5
_database_code_depnum_ccdc_archive 'CCDC 1964878'
loop_
_audit_author_name
_audit_author_address
'Hadi Rudbari'
;Isfahan University
Iran
;
_audit_update_record             
;
2019-11-09 deposited with the CCDC.	2020-06-02 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            'C30 H24 Cl4 Cu N2 O2'
_chemical_formula_weight         649.85

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

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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'

_cell_length_a                   8.6322(2)
_cell_length_b                   14.8439(3)
_cell_length_c                   11.1572(3)
_cell_angle_alpha                90
_cell_angle_beta                 97.8710(10)
_cell_angle_gamma                90
_cell_volume                     1416.16(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    9726
_cell_measurement_theta_min      2.30
_cell_measurement_theta_max      29.59

_exptl_crystal_description       prismatic
_exptl_crystal_colour            'dark black'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.524
_exptl_crystal_F_000             662
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.51
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.21
_exptl_absorpt_coefficient_mu    1.180
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.639
_exptl_absorpt_correction_T_max  0.814
_exptl_absorpt_process_details   'SADABS; Bruker, 2008'
_diffrn_ambient_temperature      273(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            79451
_diffrn_reflns_av_unetI/netI     0.0390
_diffrn_reflns_av_R_equivalents  0.0669
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.297
_diffrn_reflns_theta_max         32.581
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             10276
_reflns_number_gt                8716
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.935
_reflns_Friedel_fraction_max     0.997
_reflns_Friedel_fraction_full    1.000

_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, 2007)'
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_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)+(0.0434P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 3767 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.005(4)
_chemical_absolute_configuration rmad
_refine_ls_number_reflns         10276
_refine_ls_number_parameters     352
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0378
_refine_ls_R_factor_gt           0.0288
_refine_ls_wR_factor_ref         0.0729
_refine_ls_wR_factor_gt          0.0659
_refine_ls_goodness_of_fit_ref   0.993
_refine_ls_restrained_S_all      0.993
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.68563(3) 0.58174(2) 0.56929(2) 0.02621(6) Uani 1 1 d . . . . .
Cl1 Cl 0.43951(7) 0.61740(6) 0.16975(5) 0.04841(17) Uani 1 1 d . . . . .
Cl2 Cl -0.12205(7) 0.65320(5) 0.32352(6) 0.04471(15) Uani 1 1 d . . . . .
N1 N 0.5263(2) 0.62390(13) 0.66846(14) 0.0261(3) Uani 1 1 d . . . . .
C22 C 0.9583(2) 0.55393(15) 0.73678(19) 0.0287(4) Uani 1 1 d . . . . .
Cl3 Cl 1.03251(9) 0.68664(5) 0.90028(7) 0.05144(17) Uani 1 1 d . . . . .
Cl4 Cl 1.26013(13) 0.35074(7) 0.96919(9) 0.0787(3) Uani 1 1 d . . . . .
O1 O 0.55478(17) 0.59936(11) 0.42223(13) 0.0296(3) Uani 1 1 d . . . . .
O2 O 0.86426(18) 0.61237(11) 0.67968(14) 0.0320(3) Uani 1 1 d . . . . .
N2 N 0.7914(2) 0.47342(13) 0.51201(16) 0.0286(4) Uani 1 1 d . . . . .
C8 C 0.5781(3) 0.63786(16) 0.80009(17) 0.0289(4) Uani 1 1 d . . . . .
H8 H 0.673444 0.674417 0.806379 0.035 Uiso 1 1 calc R U . . .
C10 C 0.6247(3) 0.54860(19) 0.8603(2) 0.0363(5) Uani 1 1 d . . . . .
C15 C 0.5761(5) 0.4668(2) 0.8105(3) 0.0557(8) Uani 1 1 d . . . . .
H15 H 0.508476 0.464362 0.738082 0.067 Uiso 1 1 calc R U . . .
C14 C 0.6294(7) 0.3872(3) 0.8700(4) 0.0849(14) Uani 1 1 d . . . . .
H14 H 0.599558 0.331737 0.835486 0.102 Uiso 1 1 calc R U . . .
C13 C 0.7243(6) 0.3904(4) 0.9774(5) 0.0926(18) Uani 1 1 d . . . . .
H13 H 0.758251 0.336988 1.016002 0.111 Uiso 1 1 calc R U . . .
C12 C 0.7708(5) 0.4714(4) 1.0298(4) 0.0811(14) Uani 1 1 d . . . . .
H12 H 0.835326 0.472979 1.103660 0.097 Uiso 1 1 calc R U . . .
C11 C 0.7206(3) 0.5511(3) 0.9713(3) 0.0551(8) Uani 1 1 d . . . . .
H11 H 0.751123 0.606219 1.006527 0.066 Uiso 1 1 calc R U . . .
C1 C 0.3807(3) 0.63179(16) 0.62679(19) 0.0294(4) Uani 1 1 d . . . . .
H1 H 0.312141 0.642386 0.682689 0.035 Uiso 1 1 calc R U . . .
C2 C 0.3133(2) 0.62571(16) 0.50059(18) 0.0272(4) Uani 1 1 d . . . . .
C4 C 0.0800(2) 0.64123(17) 0.3563(2) 0.0327(4) Uani 1 1 d . . . . .
C5 C 0.1681(3) 0.63614(19) 0.2609(2) 0.0348(5) Uani 1 1 d . . . . .
H5 H 0.120240 0.640722 0.181183 0.042 Uiso 1 1 calc R U . . .
C6 C 0.3272(3) 0.62420(18) 0.28681(18) 0.0306(4) Uani 1 1 d . . . . .
C7 C 0.4068(2) 0.61493(15) 0.40612(18) 0.0261(4) Uani 1 1 d . . . . .
C17 C 0.9801(3) 0.46560(16) 0.6953(2) 0.0332(5) Uani 1 1 d . . . . .
C16 C 0.9033(3) 0.43385(17) 0.5798(2) 0.0352(5) Uani 1 1 d . . . . .
H16 H 0.938292 0.379494 0.551925 0.042 Uiso 1 1 calc R U . . .
C23 C 0.7219(3) 0.43143(16) 0.3965(2) 0.0310(4) Uani 1 1 d . . . . .
H23 H 0.701409 0.480240 0.337357 0.037 Uiso 1 1 calc R U . . .
C25 C 0.5641(3) 0.39061(16) 0.4121(2) 0.0338(5) Uani 1 1 d . . . . .
C26 C 0.4454(3) 0.3912(2) 0.3148(3) 0.0451(6) Uani 1 1 d . . . . .
H26 H 0.462399 0.417439 0.242040 0.054 Uiso 1 1 calc R U . . .
C27 C 0.3008(3) 0.3526(2) 0.3255(3) 0.0568(8) Uani 1 1 d . . . . .
H27 H 0.222209 0.352571 0.259535 0.068 Uiso 1 1 calc R U . . .
C28 C 0.2733(4) 0.3142(2) 0.4338(4) 0.0569(8) Uani 1 1 d . . . . .
H28 H 0.176238 0.289300 0.441285 0.068 Uiso 1 1 calc R U . . .
C29 C 0.3913(4) 0.3132(2) 0.5300(3) 0.0528(7) Uani 1 1 d . . . . .
H29 H 0.374170 0.287276 0.602857 0.063 Uiso 1 1 calc R U . . .
C30 C 0.5358(3) 0.35078(18) 0.5189(2) 0.0409(5) Uani 1 1 d . . . . .
H30 H 0.614885 0.349143 0.584481 0.049 Uiso 1 1 calc R U . . .
C24 C 0.8274(3) 0.3639(2) 0.3439(2) 0.0421(6) Uani 1 1 d . . . . .
H24A H 0.773872 0.339972 0.269636 0.063 Uiso 1 1 calc R U . . .
H24B H 0.921564 0.393463 0.328476 0.063 Uiso 1 1 calc R U . . .
H24C H 0.853164 0.315697 0.400538 0.063 Uiso 1 1 calc R U . . .
C18 C 1.0767(3) 0.40393(19) 0.7660(2) 0.0429(6) Uani 1 1 d . . . . .
H18 H 1.089232 0.345879 0.737492 0.051 Uiso 1 1 calc R U . . .
C19 C 1.1525(3) 0.4293(2) 0.8771(3) 0.0451(6) Uani 1 1 d . . . . .
C20 C 1.1427(3) 0.5166(2) 0.9175(2) 0.0429(6) Uani 1 1 d . . . . .
H20 H 1.198879 0.534340 0.990815 0.051 Uiso 1 1 calc R U . . .
C21 C 1.0492(2) 0.5771(2) 0.84837(19) 0.0342(4) Uani 1 1 d . . . . .
C9 C 0.4635(3) 0.68915(19) 0.8673(2) 0.0391(5) Uani 1 1 d . . . . .
H9A H 0.506356 0.694911 0.951019 0.059 Uiso 1 1 calc R U . . .
H9B H 0.445584 0.747955 0.832362 0.059 Uiso 1 1 calc R U . . .
H9C H 0.366341 0.656860 0.860919 0.059 Uiso 1 1 calc R U . . .
C3 C 0.1500(2) 0.63698(17) 0.4738(2) 0.0308(4) Uani 1 1 d . . . . .
H3 H 0.089516 0.641546 0.536447 0.037 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 O1 1.8785(14) . ?
Cu1 O2 1.8924(15) . ?
Cu1 N1 1.9807(17) . ?
Cu1 N2 1.9970(19) . ?
Cl1 C6 1.733(2) . ?
Cl2 C4 1.742(2) . ?
N1 C1 1.285(3) . ?
N1 C8 1.490(2) . ?
C22 O2 1.295(3) . ?
C22 C17 1.412(3) . ?
C22 C21 1.420(3) . ?
Cl3 C21 1.739(3) . ?
Cl4 C19 1.737(3) . ?
O1 C7 1.286(2) . ?
N2 C16 1.285(3) . ?
N2 C23 1.482(3) . ?
C8 C10 1.515(3) . ?
C8 C9 1.525(3) . ?
C8 H8 0.9800 . ?
C10 C15 1.377(5) . ?
C10 C11 1.392(4) . ?
C15 C14 1.402(5) . ?
C15 H15 0.9300 . ?
C14 C13 1.357(7) . ?
C14 H14 0.9300 . ?
C13 C12 1.373(8) . ?
C13 H13 0.9300 . ?
C12 C11 1.391(5) . ?
C12 H12 0.9300 . ?
C11 H11 0.9300 . ?
C1 C2 1.451(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.410(3) . ?
C2 C7 1.422(3) . ?
C4 C3 1.368(3) . ?
C4 C5 1.392(3) . ?
C5 C6 1.376(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.419(3) . ?
C17 C18 1.406(3) . ?
C17 C16 1.444(3) . ?
C16 H16 0.9300 . ?
C23 C25 1.522(3) . ?
C23 C24 1.525(3) . ?
C23 H23 0.9800 . ?
C25 C30 1.382(4) . ?
C25 C26 1.387(4) . ?
C26 C27 1.394(4) . ?
C26 H26 0.9300 . ?
C27 C28 1.385(5) . ?
C27 H27 0.9300 . ?
C28 C29 1.375(5) . ?
C28 H28 0.9300 . ?
C29 C30 1.387(4) . ?
C29 H29 0.9300 . ?
C30 H30 0.9300 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C18 C19 1.373(4) . ?
C18 H18 0.9300 . ?
C19 C20 1.378(4) . ?
C20 C21 1.372(4) . ?
C20 H20 0.9300 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C3 H3 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Cu1 O2 150.92(7) . . ?
O1 Cu1 N1 93.65(7) . . ?
O2 Cu1 N1 97.28(7) . . ?
O1 Cu1 N2 94.55(7) . . ?
O2 Cu1 N2 91.95(7) . . ?
N1 Cu1 N2 144.70(8) . . ?
C1 N1 C8 119.39(18) . . ?
C1 N1 Cu1 123.13(14) . . ?
C8 N1 Cu1 117.19(13) . . ?
O2 C22 C17 124.3(2) . . ?
O2 C22 C21 120.2(2) . . ?
C17 C22 C21 115.5(2) . . ?
C7 O1 Cu1 127.87(13) . . ?
C22 O2 Cu1 124.03(14) . . ?
C16 N2 C23 120.1(2) . . ?
C16 N2 Cu1 121.30(16) . . ?
C23 N2 Cu1 117.92(14) . . ?
N1 C8 C10 109.97(19) . . ?
N1 C8 C9 115.27(19) . . ?
C10 C8 C9 111.66(18) . . ?
N1 C8 H8 106.5 . . ?
C10 C8 H8 106.5 . . ?
C9 C8 H8 106.5 . . ?
C15 C10 C11 119.6(3) . . ?
C15 C10 C8 123.0(2) . . ?
C11 C10 C8 117.4(3) . . ?
C10 C15 C14 119.3(4) . . ?
C10 C15 H15 120.3 . . ?
C14 C15 H15 120.3 . . ?
C13 C14 C15 120.6(4) . . ?
C13 C14 H14 119.7 . . ?
C15 C14 H14 119.7 . . ?
C14 C13 C12 120.8(3) . . ?
C14 C13 H13 119.6 . . ?
C12 C13 H13 119.6 . . ?
C13 C12 C11 119.4(4) . . ?
C13 C12 H12 120.3 . . ?
C11 C12 H12 120.3 . . ?
C12 C11 C10 120.2(4) . . ?
C12 C11 H11 119.9 . . ?
C10 C11 H11 119.9 . . ?
N1 C1 C2 126.03(19) . . ?
N1 C1 H1 117.0 . . ?
C2 C1 H1 117.0 . . ?
C3 C2 C7 120.61(18) . . ?
C3 C2 C1 117.04(18) . . ?
C7 C2 C1 122.22(18) . . ?
C3 C4 C5 121.0(2) . . ?
C3 C4 Cl2 120.26(17) . . ?
C5 C4 Cl2 118.72(17) . . ?
C6 C5 C4 118.7(2) . . ?
C6 C5 H5 120.7 . . ?
C4 C5 H5 120.7 . . ?
C5 C6 C7 123.44(19) . . ?
C5 C6 Cl1 119.63(16) . . ?
C7 C6 Cl1 116.92(16) . . ?
O1 C7 C6 119.51(18) . . ?
O1 C7 C2 124.80(18) . . ?
C6 C7 C2 115.68(18) . . ?
C18 C17 C22 121.1(2) . . ?
C18 C17 C16 116.9(2) . . ?
C22 C17 C16 122.0(2) . . ?
N2 C16 C17 126.3(2) . . ?
N2 C16 H16 116.8 . . ?
C17 C16 H16 116.8 . . ?
N2 C23 C25 109.31(18) . . ?
N2 C23 C24 114.78(19) . . ?
C25 C23 C24 111.9(2) . . ?
N2 C23 H23 106.8 . . ?
C25 C23 H23 106.8 . . ?
C24 C23 H23 106.8 . . ?
C30 C25 C26 118.6(3) . . ?
C30 C25 C23 122.4(2) . . ?
C26 C25 C23 119.0(2) . . ?
C25 C26 C27 120.3(3) . . ?
C25 C26 H26 119.8 . . ?
C27 C26 H26 119.8 . . ?
C28 C27 C26 120.4(3) . . ?
C28 C27 H27 119.8 . . ?
C26 C27 H27 119.8 . . ?
C29 C28 C27 119.2(3) . . ?
C29 C28 H28 120.4 . . ?
C27 C28 H28 120.4 . . ?
C28 C29 C30 120.4(3) . . ?
C28 C29 H29 119.8 . . ?
C30 C29 H29 119.8 . . ?
C25 C30 C29 121.1(3) . . ?
C25 C30 H30 119.5 . . ?
C29 C30 H30 119.5 . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C19 C18 C17 120.1(3) . . ?
C19 C18 H18 120.0 . . ?
C17 C18 H18 120.0 . . ?
C18 C19 C20 120.7(2) . . ?
C18 C19 Cl4 120.0(2) . . ?
C20 C19 Cl4 119.3(2) . . ?
C21 C20 C19 119.3(2) . . ?
C21 C20 H20 120.4 . . ?
C19 C20 H20 120.4 . . ?
C20 C21 C22 123.1(3) . . ?
C20 C21 Cl3 119.60(18) . . ?
C22 C21 Cl3 117.2(2) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C4 C3 C2 120.4(2) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 Cu1 O1 C7 -124.33(19) . . . . ?
N1 Cu1 O1 C7 -12.26(19) . . . . ?
N2 Cu1 O1 C7 133.36(18) . . . . ?
C17 C22 O2 Cu1 25.3(3) . . . . ?
C21 C22 O2 Cu1 -155.24(16) . . . . ?
O1 Cu1 O2 C22 -137.22(17) . . . . ?
N1 Cu1 O2 C22 111.59(17) . . . . ?
N2 Cu1 O2 C22 -34.25(18) . . . . ?
C1 N1 C8 C10 108.5(2) . . . . ?
Cu1 N1 C8 C10 -65.5(2) . . . . ?
C1 N1 C8 C9 -18.8(3) . . . . ?
Cu1 N1 C8 C9 167.23(17) . . . . ?
N1 C8 C10 C15 -20.1(3) . . . . ?
C9 C8 C10 C15 109.1(3) . . . . ?
N1 C8 C10 C11 160.1(2) . . . . ?
C9 C8 C10 C11 -70.6(3) . . . . ?
C11 C10 C15 C14 -2.7(5) . . . . ?
C8 C10 C15 C14 177.6(3) . . . . ?
C10 C15 C14 C13 2.0(6) . . . . ?
C15 C14 C13 C12 -0.4(7) . . . . ?
C14 C13 C12 C11 -0.4(7) . . . . ?
C13 C12 C11 C10 -0.4(6) . . . . ?
C15 C10 C11 C12 2.0(4) . . . . ?
C8 C10 C11 C12 -178.3(3) . . . . ?
C8 N1 C1 C2 176.0(2) . . . . ?
Cu1 N1 C1 C2 -10.3(3) . . . . ?
N1 C1 C2 C3 -179.6(2) . . . . ?
N1 C1 C2 C7 -3.7(4) . . . . ?
C3 C4 C5 C6 1.8(4) . . . . ?
Cl2 C4 C5 C6 -178.2(2) . . . . ?
C4 C5 C6 C7 1.3(4) . . . . ?
C4 C5 C6 Cl1 179.9(2) . . . . ?
Cu1 O1 C7 C6 -178.43(17) . . . . ?
Cu1 O1 C7 C2 2.8(3) . . . . ?
C5 C6 C7 O1 176.4(2) . . . . ?
Cl1 C6 C7 O1 -2.1(3) . . . . ?
C5 C6 C7 C2 -4.7(4) . . . . ?
Cl1 C6 C7 C2 176.69(18) . . . . ?
C3 C2 C7 O1 -176.0(2) . . . . ?
C1 C2 C7 O1 8.3(4) . . . . ?
C3 C2 C7 C6 5.3(3) . . . . ?
C1 C2 C7 C6 -170.5(2) . . . . ?
O2 C22 C17 C18 -175.8(2) . . . . ?
C21 C22 C17 C18 4.7(3) . . . . ?
O2 C22 C17 C16 3.3(4) . . . . ?
C21 C22 C17 C16 -176.1(2) . . . . ?
C23 N2 C16 C17 -178.7(2) . . . . ?
Cu1 N2 C16 C17 -8.1(4) . . . . ?
C18 C17 C16 N2 167.3(3) . . . . ?
C22 C17 C16 N2 -11.9(4) . . . . ?
C16 N2 C23 C25 104.0(3) . . . . ?
Cu1 N2 C23 C25 -67.0(2) . . . . ?
C16 N2 C23 C24 -22.7(3) . . . . ?
Cu1 N2 C23 C24 166.39(17) . . . . ?
N2 C23 C25 C30 -35.6(3) . . . . ?
C24 C23 C25 C30 92.7(3) . . . . ?
N2 C23 C25 C26 146.1(2) . . . . ?
C24 C23 C25 C26 -85.6(3) . . . . ?
C30 C25 C26 C27 0.3(4) . . . . ?
C23 C25 C26 C27 178.6(3) . . . . ?
C25 C26 C27 C28 0.8(5) . . . . ?
C26 C27 C28 C29 -1.1(5) . . . . ?
C27 C28 C29 C30 0.4(5) . . . . ?
C26 C25 C30 C29 -1.0(4) . . . . ?
C23 C25 C30 C29 -179.3(3) . . . . ?
C28 C29 C30 C25 0.6(5) . . . . ?
C22 C17 C18 C19 -0.4(4) . . . . ?
C16 C17 C18 C19 -179.6(3) . . . . ?
C17 C18 C19 C20 -3.9(5) . . . . ?
C17 C18 C19 Cl4 175.2(2) . . . . ?
C18 C19 C20 C21 3.5(4) . . . . ?
Cl4 C19 C20 C21 -175.6(2) . . . . ?
C19 C20 C21 C22 1.2(4) . . . . ?
C19 C20 C21 Cl3 178.5(2) . . . . ?
O2 C22 C21 C20 175.3(2) . . . . ?
C17 C22 C21 C20 -5.2(3) . . . . ?
O2 C22 C21 Cl3 -2.0(3) . . . . ?
C17 C22 C21 Cl3 177.47(17) . . . . ?
C5 C4 C3 C2 -1.1(4) . . . . ?
Cl2 C4 C3 C2 178.89(19) . . . . ?
C7 C2 C3 C4 -2.6(4) . . . . ?
C1 C2 C3 C4 173.4(2) . . . . ?

_refine_diff_density_max         0.594
_refine_diff_density_min         -0.352
_refine_diff_density_rms         0.082

