# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2023

####################################################################### 
# 
# 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 2221840'
loop_
_audit_author_name
_audit_author_address
'Behrouz Notash'
;Shahid Beheshti University
Iran
;
_audit_update_record             
;
2022-11-24 deposited with the CCDC.	2023-07-17 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         'C7 H6 Cd I2 N2'
_chemical_formula_sum            'C7 H6 Cd I2 N2'
_chemical_formula_weight         484.35

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cd Cd -0.8075 1.2024 '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           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

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

_cell_length_a                   13.601(3)
_cell_length_b                   12.138(2)
_cell_length_c                   13.945(3)
_cell_angle_alpha                90
_cell_angle_beta                 94.52(3)
_cell_angle_gamma                90
_cell_volume                     2295.0(8)
_cell_formula_units_Z            8
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    2018
_cell_measurement_theta_min      2.252
_cell_measurement_theta_max      24.998

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.804
_exptl_crystal_F_000             1728
_exptl_transmission_factor_min   0.186
_exptl_transmission_factor_max   0.410
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.350
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    7.238
_shelx_estimated_absorpt_T_min   0.186
_shelx_estimated_absorpt_T_max   0.410
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   'shape of crystal determined optically'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'STOE IPDS 2T'
_diffrn_measurement_method       'rotation method'
_diffrn_detector_area_resol_mean '0.15 mm'
_diffrn_reflns_number            6127
_diffrn_reflns_av_unetI/netI     0.0938
_diffrn_reflns_av_R_equivalents  0.1057
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.252
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_full        24.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2018
_reflns_number_gt                1317
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'X-Area (Stoe & Cie GmbH, 2005)'
_computing_cell_refinement       'X-Area (Stoe & Cie GmbH, 2005)'
_computing_data_reduction        'X-Area (Stoe & Cie GmbH, 2005)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_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)+(0.0636P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2018
_refine_ls_number_parameters     116
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0822
_refine_ls_R_factor_gt           0.0526
_refine_ls_wR_factor_ref         0.1275
_refine_ls_wR_factor_gt          0.1195
_refine_ls_goodness_of_fit_ref   0.911
_refine_ls_restrained_S_all      0.911
_refine_ls_shift/su_max          0.010
_refine_ls_shift/su_mean         0.001

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cd1 Cd 0.500000 0.77692(11) 0.250000 0.0392(3) Uani 1 2 d S T P . .
Cd2 Cd 0.500000 1.09191(12) 0.250000 0.0481(4) Uani 1 2 d S T P . .
I1 I 0.41904(6) 0.93602(8) 0.37539(6) 0.0494(3) Uani 1 1 d . . . . .
I2 I 0.34455(6) 1.20801(9) 0.16658(8) 0.0625(3) Uani 1 1 d . . . . .
N1 N 0.6526(7) 0.7753(11) 0.3584(8) 0.049(3) Uani 1 1 d D . . . .
N2 N 0.5728(8) 0.3722(12) 0.6720(9) 0.057(3) Uani 1 1 d . . . . .
C1 C 0.6479(8) 0.6954(12) 0.4305(9) 0.043(3) Uani 1 1 d . . . . .
C2 C 0.6014(9) 0.7156(12) 0.5132(9) 0.046(3) Uani 1 1 d . . . . .
H2 H 0.579647 0.786440 0.525744 0.056 Uiso 1 1 calc R U . . .
C3 C 0.6796(9) 0.5901(13) 0.4154(9) 0.051(4) Uani 1 1 d . . . . .
H3 H 0.711202 0.574970 0.360159 0.061 Uiso 1 1 calc R U . . .
C4 C 0.5869(8) 0.6324(11) 0.5770(9) 0.041(3) Uani 1 1 d . . . . .
H4 H 0.556015 0.648067 0.632645 0.049 Uiso 1 1 calc R U . . .
C5 C 0.6662(9) 0.5058(12) 0.4795(9) 0.050(3) Uani 1 1 d . . . . .
H5 H 0.690238 0.435676 0.468218 0.060 Uiso 1 1 calc R U . . .
C6 C 0.6170(7) 0.5263(11) 0.5607(9) 0.040(3) Uani 1 1 d . . . . .
C7 C 0.5934(8) 0.4378(13) 0.6222(10) 0.046(3) Uani 1 1 d . . . . .
H1A H 0.702(6) 0.771(12) 0.323(7) 0.055 Uiso 1 1 d D U . . .
H1B H 0.628(10) 0.841(5) 0.362(10) 0.055 Uiso 1 1 d D U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cd1 N2 2.368(14) 6_565 ?
Cd1 N2 2.368(14) 5_666 ?
Cd1 N1 2.470(9) . ?
Cd1 N1 2.470(9) 2_655 ?
Cd1 I1 2.8815(14) . ?
Cd1 I1 2.8815(14) 2_655 ?
Cd2 I2 2.7243(13) . ?
Cd2 I2 2.7243(13) 2_655 ?
Cd2 I1 2.8555(14) . ?
Cd2 I1 2.8555(14) 2_655 ?
N1 C1 1.402(17) . ?
N1 H1A 0.87(2) . ?
N1 H1B 0.87(2) . ?
N2 C7 1.107(17) . ?
C1 C3 1.370(19) . ?
C1 C2 1.381(18) . ?
C2 C4 1.370(19) . ?
C2 H2 0.9300 . ?
C3 C5 1.380(19) . ?
C3 H3 0.9300 . ?
C4 C6 1.376(18) . ?
C4 H4 0.9300 . ?
C5 C6 1.382(17) . ?
C5 H5 0.9300 . ?
C6 C7 1.43(2) . ?

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
N2 Cd1 N2 80.3(6) 6_565 5_666 ?
N2 Cd1 N1 85.0(4) 6_565 . ?
N2 Cd1 N1 94.3(4) 5_666 . ?
N2 Cd1 N1 94.3(4) 6_565 2_655 ?
N2 Cd1 N1 85.0(4) 5_666 2_655 ?
N1 Cd1 N1 179.1(6) . 2_655 ?
N2 Cd1 I1 169.9(3) 6_565 . ?
N2 Cd1 I1 92.3(3) 5_666 . ?
N1 Cd1 I1 88.7(3) . . ?
N1 Cd1 I1 91.9(3) 2_655 . ?
N2 Cd1 I1 92.3(3) 6_565 2_655 ?
N2 Cd1 I1 169.9(3) 5_666 2_655 ?
N1 Cd1 I1 91.9(3) . 2_655 ?
N1 Cd1 I1 88.7(3) 2_655 2_655 ?
I1 Cd1 I1 95.84(6) . 2_655 ?
I2 Cd2 I2 117.70(7) . 2_655 ?
I2 Cd2 I1 106.29(3) . . ?
I2 Cd2 I1 113.89(3) 2_655 . ?
I2 Cd2 I1 113.89(3) . 2_655 ?
I2 Cd2 I1 106.29(3) 2_655 2_655 ?
I1 Cd2 I1 97.00(6) . 2_655 ?
Cd2 I1 Cd1 83.58(4) . . ?
C1 N1 Cd1 111.2(7) . . ?
C1 N1 H1A 116(9) . . ?
Cd1 N1 H1A 108(8) . . ?
C1 N1 H1B 124(9) . . ?
Cd1 N1 H1B 74(9) . . ?
H1A N1 H1B 114(10) . . ?
C7 N2 Cd1 166.7(11) . 5_666 ?
C3 C1 C2 117.7(13) . . ?
C3 C1 N1 120.2(12) . . ?
C2 C1 N1 121.7(13) . . ?
C4 C2 C1 120.7(13) . . ?
C4 C2 H2 119.6 . . ?
C1 C2 H2 119.6 . . ?
C1 C3 C5 122.2(12) . . ?
C1 C3 H3 118.9 . . ?
C5 C3 H3 118.9 . . ?
C2 C4 C6 121.5(12) . . ?
C2 C4 H4 119.3 . . ?
C6 C4 H4 119.3 . . ?
C3 C5 C6 119.6(13) . . ?
C3 C5 H5 120.2 . . ?
C6 C5 H5 120.2 . . ?
C4 C6 C5 118.3(12) . . ?
C4 C6 C7 121.4(11) . . ?
C5 C6 C7 120.2(13) . . ?
N2 C7 C6 177.0(16) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cd1 N1 C1 C3 89.4(11) . . . . ?
Cd1 N1 C1 C2 -82.9(13) . . . . ?
C3 C1 C2 C4 -0.6(17) . . . . ?
N1 C1 C2 C4 171.8(11) . . . . ?
C2 C1 C3 C5 0.1(18) . . . . ?
N1 C1 C3 C5 -172.5(11) . . . . ?
C1 C2 C4 C6 -0.7(18) . . . . ?
C1 C3 C5 C6 1.8(19) . . . . ?
C2 C4 C6 C5 2.6(17) . . . . ?
C2 C4 C6 C7 -173.8(11) . . . . ?
C3 C5 C6 C4 -3.1(17) . . . . ?
C3 C5 C6 C7 173.3(11) . . . . ?

_refine_diff_density_max         1.755
_refine_diff_density_min         -1.661
_refine_diff_density_rms         0.267

####################################################################### 
# 
# 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 2221841'
loop_
_audit_author_name
_audit_author_address
'Behrouz Notash'
;Shahid Beheshti University
Iran
;
_audit_update_record             
;
2022-11-24 deposited with the CCDC.	2023-07-17 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         'C7 H6 Br2 Cd N2'
_chemical_formula_sum            'C7 H6 Br2 Cd N2'
_chemical_formula_weight         390.35

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cd Cd -0.8075 1.2024 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   10.844(2)
_cell_length_b                   7.1695(14)
_cell_length_c                   13.048(3)
_cell_angle_alpha                90
_cell_angle_beta                 93.90(3)
_cell_angle_gamma                90
_cell_volume                     1012.1(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    1782
_cell_measurement_theta_min      3.130
_cell_measurement_theta_max      24.990

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.562
_exptl_crystal_F_000             720
_exptl_transmission_factor_min   0.103
_exptl_transmission_factor_max   0.368
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    10.000
_shelx_estimated_absorpt_T_min   0.189
_shelx_estimated_absorpt_T_max   0.435
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   'shape of crystal determined optically'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'STOE IPDS 2T'
_diffrn_measurement_method       'rotation method'
_diffrn_detector_area_resol_mean '0.15 mm'
_diffrn_reflns_number            4378
_diffrn_reflns_av_unetI/netI     0.1497
_diffrn_reflns_av_R_equivalents  0.1357
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.130
_diffrn_reflns_theta_max         24.990
_diffrn_reflns_theta_full        24.990
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             1782
_reflns_number_gt                1016
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'X-Area (Stoe & Cie GmbH, 2005)'
_computing_cell_refinement       'X-Area (Stoe & Cie GmbH, 2005)'
_computing_data_reduction        'X-Area (Stoe & Cie GmbH, 2005)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_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)+(0.0547P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1782
_refine_ls_number_parameters     79
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.1191
_refine_ls_R_factor_gt           0.0605
_refine_ls_wR_factor_ref         0.1398
_refine_ls_wR_factor_gt          0.1248
_refine_ls_goodness_of_fit_ref   0.900
_refine_ls_restrained_S_all      0.900
_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
Cd1 Cd 0.07019(9) 0.01277(17) 0.63570(9) 0.0303(3) Uani 1 1 d . . . . .
Br1 Br 0.02634(14) 0.1682(2) 0.82133(13) 0.0362(5) Uani 1 1 d . . . . .
Br2 Br -0.15131(13) 0.1294(2) 0.54249(13) 0.0344(4) Uani 1 1 d . . . . .
N1 N 0.1529(11) 0.3045(19) 0.5808(12) 0.0371(15) Uani 1 1 d D . . . .
N2 N 0.7372(12) 0.435(2) 0.7806(12) 0.049(4) Uani 1 1 d . . . . .
C1 C 0.2782(13) 0.344(2) 0.6182(13) 0.0371(15) Uani 1 1 d . . . . .
C2 C 0.3006(13) 0.408(2) 0.7156(13) 0.0371(15) Uani 1 1 d . . . . .
H2 H 0.235579 0.438425 0.755421 0.045 Uiso 1 1 calc R U . . .
C3 C 0.3729(12) 0.309(2) 0.5586(13) 0.0371(15) Uani 1 1 d . . . . .
H3 H 0.355850 0.270976 0.491017 0.045 Uiso 1 1 calc R U . . .
C4 C 0.4209(13) 0.426(2) 0.7544(14) 0.0371(15) Uani 1 1 d . . . . .
H4 H 0.436197 0.464964 0.822140 0.045 Uiso 1 1 calc R U . . .
C5 C 0.4947(13) 0.329(2) 0.5962(13) 0.0371(15) Uani 1 1 d . . . . .
H5 H 0.558723 0.301390 0.554698 0.045 Uiso 1 1 calc R U . . .
C6 C 0.5202(13) 0.390(2) 0.6963(14) 0.0371(15) Uani 1 1 d . . . . .
C7 C 0.6431(14) 0.414(2) 0.7411(16) 0.042(5) Uani 1 1 d . . . . .
H1A H 0.130(13) 0.415(11) 0.601(11) 0.050 Uiso 1 1 d D U . . .
H1B H 0.173(13) 0.35(2) 0.524(6) 0.050 Uiso 1 1 d D U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cd1 N2 2.357(12) 2_646 ?
Cd1 N1 2.404(14) . ?
Cd1 Br1 2.737(2) . ?
Cd1 Br2 2.738(2) 3_556 ?
Cd1 Br2 2.7477(18) . ?
Cd1 Br1 2.755(2) 2_546 ?
N1 H1B 0.87(2) . ?
N1 C1 1.440(19) . ?
N1 H1A 0.87(2) . ?
N1 H1B 0.87(2) . ?
N2 C7 1.121(17) . ?
C1 C3 1.35(2) . ?
C1 C2 1.36(2) . ?
C2 C4 1.374(19) . ?
C2 H2 0.9300 . ?
C3 C5 1.384(19) . ?
C3 H3 0.9300 . ?
C4 C6 1.38(2) . ?
C4 H4 0.9300 . ?
C5 C6 1.39(2) . ?
C5 H5 0.9300 . ?
C6 C7 1.43(2) . ?

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
N2 Cd1 N1 90.4(5) 2_646 . ?
N2 Cd1 Br1 83.6(4) 2_646 . ?
N1 Cd1 Br1 90.0(4) . . ?
N2 Cd1 Br2 88.8(4) 2_646 3_556 ?
N1 Cd1 Br2 85.6(4) . 3_556 ?
Br1 Cd1 Br2 171.20(6) . 3_556 ?
N2 Cd1 Br2 175.9(4) 2_646 . ?
N1 Cd1 Br2 86.3(3) . . ?
Br1 Cd1 Br2 93.93(6) . . ?
Br2 Cd1 Br2 93.39(6) 3_556 . ?
N2 Cd1 Br1 91.7(4) 2_646 2_546 ?
N1 Cd1 Br1 174.4(4) . 2_546 ?
Br1 Cd1 Br1 95.38(5) . 2_546 ?
Br2 Cd1 Br1 89.29(7) 3_556 2_546 ?
Br2 Cd1 Br1 91.73(6) . 2_546 ?
Cd1 Br1 Cd1 129.52(7) . 2_556 ?
Cd1 Br2 Cd1 86.61(6) 3_556 . ?
H1B N1 C1 86(10) . . ?
H1B N1 Cd1 137(10) . . ?
C1 N1 Cd1 115.6(10) . . ?
H1B N1 H1A 89(4) . . ?
C1 N1 H1A 90(10) . . ?
Cd1 N1 H1A 125(10) . . ?
H1B N1 H1B 0(5) . . ?
C1 N1 H1B 86(10) . . ?
Cd1 N1 H1B 137(10) . . ?
H1A N1 H1B 89(4) . . ?
C7 N2 Cd1 173.9(14) . 2_656 ?
C3 C1 C2 120.4(14) . . ?
C3 C1 N1 120.4(15) . . ?
C2 C1 N1 119.2(15) . . ?
C1 C2 C4 118.9(17) . . ?
C1 C2 H2 120.6 . . ?
C4 C2 H2 120.6 . . ?
C1 C3 C5 121.4(16) . . ?
C1 C3 H3 119.3 . . ?
C5 C3 H3 119.3 . . ?
C2 C4 C6 122.3(17) . . ?
C2 C4 H4 118.8 . . ?
C6 C4 H4 118.8 . . ?
C3 C5 C6 119.3(16) . . ?
C3 C5 H5 120.3 . . ?
C6 C5 H5 120.3 . . ?
C4 C6 C5 117.6(14) . . ?
C4 C6 C7 119.5(17) . . ?
C5 C6 C7 122.9(17) . . ?
N2 C7 C6 177(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
H1B N1 C1 C3 -43(10) . . . . ?
Cd1 N1 C1 C3 97.8(17) . . . . ?
H1B N1 C1 C2 140(10) . . . . ?
Cd1 N1 C1 C2 -79.1(17) . . . . ?
C3 C1 C2 C4 -4(3) . . . . ?
N1 C1 C2 C4 173.2(14) . . . . ?
C2 C1 C3 C5 3(3) . . . . ?
N1 C1 C3 C5 -173.8(14) . . . . ?
C1 C2 C4 C6 3(2) . . . . ?
C1 C3 C5 C6 -2(3) . . . . ?
C2 C4 C6 C5 -1(2) . . . . ?
C2 C4 C6 C7 179.3(15) . . . . ?
C3 C5 C6 C4 1(2) . . . . ?
C3 C5 C6 C7 -180.0(15) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1A Br1 0.87(2) 2.73(6) 3.541(15) 156(13) 2_556

_refine_diff_density_max         1.440
_refine_diff_density_min         -1.129
_refine_diff_density_rms         0.266

####################################################################### 
# 
# 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 2221843'
loop_
_audit_author_name
_audit_author_address
'Behrouz Notash'
;Shahid Beheshti University
Iran
;
_audit_update_record             
;
2022-11-24 deposited with the CCDC.	2023-07-17 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         'C18 H18 Cd N4 O4'
_chemical_formula_sum            'C18 H18 Cd N4 O4'
_chemical_formula_weight         466.77

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'
Cd Cd -0.8075 1.2024 '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           11
_space_group_name_H-M_alt        'P 21/m'
_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'
'-x, -y, -z'
'x, -y-1/2, z'

_cell_length_a                   10.834(2)
_cell_length_b                   6.9860(14)
_cell_length_c                   12.941(3)
_cell_angle_alpha                90
_cell_angle_beta                 102.90(3)
_cell_angle_gamma                90
_cell_volume                     954.7(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    1818
_cell_measurement_theta_min      2.222
_cell_measurement_theta_max      24.997

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.624
_exptl_crystal_F_000             468
_exptl_transmission_factor_min   0.5930
_exptl_transmission_factor_max   0.7209
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.300
_exptl_absorpt_coefficient_mu    1.174
_shelx_estimated_absorpt_T_min   0.591
_shelx_estimated_absorpt_T_max   0.720
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   'shape of crystal determined optically'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'STOE IPDS 2T'
_diffrn_measurement_method       'rotation method'
_diffrn_detector_area_resol_mean '0.15 mm'
_diffrn_reflns_number            4474
_diffrn_reflns_av_unetI/netI     0.0523
_diffrn_reflns_av_R_equivalents  0.0469
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.222
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_full        24.997
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             1818
_reflns_number_gt                1491
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'X-Area (Stoe & Cie GmbH, 2005)'
_computing_cell_refinement       'X-Area (Stoe & Cie GmbH, 2005)'
_computing_data_reduction        'X-Area (Stoe & Cie GmbH, 2005)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_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)+(0.0410P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1818
_refine_ls_number_parameters     149
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0453
_refine_ls_R_factor_gt           0.0331
_refine_ls_wR_factor_ref         0.0724
_refine_ls_wR_factor_gt          0.0703
_refine_ls_goodness_of_fit_ref   0.960
_refine_ls_restrained_S_all      0.960
_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
O2 O 1.0505(3) 0.0946(4) 0.59631(18) 0.0462(7) Uani 1 1 d . . . . .
Cd1 Cd 1.01071(4) 0.250000 0.42165(3) 0.03445(14) Uani 1 2 d S T P . .
O1 O 1.2123(3) 0.0957(4) 0.4173(2) 0.0647(9) Uani 1 1 d . . . . .
N4 N 0.9474(5) 0.250000 0.2344(3) 0.0509(13) Uani 1 2 d S T P . .
N3 N 0.7292(8) 0.250000 -0.2943(4) 0.076(2) Uani 1 2 d S T P . .
N1 N 0.7983(5) 0.250000 0.4454(3) 0.0386(11) Uani 1 2 d S T P . .
N2 N 0.3782(6) 0.250000 -0.0254(5) 0.0812(19) Uani 1 2 d S T P . .
C10 C 0.9081(6) 0.250000 0.1455(4) 0.0464(14) Uani 1 2 d S T P . .
C9 C 0.8578(6) 0.250000 0.0327(4) 0.0456(14) Uani 1 2 d S T P . .
C8 C 0.8356(5) 0.0802(7) -0.0226(3) 0.0673(14) Uani 1 1 d . . . . .
H8 H 0.850012 -0.035462 0.013671 0.081 Uiso 1 1 calc R U . . .
C7 C 0.7927(5) 0.0803(7) -0.1298(3) 0.0678(15) Uani 1 1 d . . . . .
H7 H 0.776503 -0.035425 -0.165789 0.081 Uiso 1 1 calc R U . . .
C6 C 0.7728(6) 0.250000 -0.1859(4) 0.0546(16) Uani 1 2 d S T P . .
C1 C 0.7036(5) 0.250000 0.3507(4) 0.0380(12) Uani 1 2 d S T P . .
C2 C 0.6589(4) 0.0788(6) 0.3032(3) 0.0487(10) Uani 1 1 d . . . . .
H2 H 0.686740 -0.036585 0.336204 0.058 Uiso 1 1 calc R U . . .
C3 C 0.5731(4) 0.0791(7) 0.2069(3) 0.0564(11) Uani 1 1 d . . . . .
H3 H 0.543030 -0.036288 0.175106 0.068 Uiso 1 1 calc R U . . .
C4 C 0.5315(6) 0.250000 0.1574(4) 0.0522(15) Uani 1 2 d S T P . .
C5 C 0.4455(7) 0.250000 0.0565(5) 0.0648(19) Uani 1 2 d S T P . .
C11 C 1.2692(7) 0.250000 0.4209(6) 0.0645(13) Uani 1 2 d S T P . .
C12 C 1.4084(7) 0.250000 0.4303(6) 0.0645(13) Uani 1 2 d S T P . .
H12A H 1.449122 0.314379 0.494442 0.097 Uiso 0.5 1 calc R U P . .
H12B H 1.427730 0.315178 0.370569 0.097 Uiso 0.5 1 calc R U P . .
H12C H 1.438360 0.120442 0.432123 0.097 Uiso 0.5 1 calc R U P . .
C13 C 1.0596(5) 0.250000 0.6455(4) 0.0330(11) Uani 1 2 d S T P . .
C14 C 1.0852(7) 0.250000 0.7642(4) 0.0552(17) Uani 1 2 d S T P . .
H14A H 1.163985 0.186183 0.792335 0.083 Uiso 0.5 1 calc R U P . .
H14B H 1.017965 0.184263 0.786833 0.083 Uiso 0.5 1 calc R U P . .
H14C H 1.089893 0.379554 0.789544 0.083 Uiso 0.5 1 calc R U P . .
H1A H 0.806(4) 0.153(7) 0.487(3) 0.066 Uiso 1 1 d . U . . .
H3A H 0.731(5) 0.158(7) -0.327(3) 0.066 Uiso 1 1 d . 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
O2 C13 1.251(3) . ?
O2 Cd1 2.457(2) . ?
O2 Cd1 2.494(3) 3_756 ?
Cd1 N4 2.367(4) . ?
Cd1 N1 2.388(5) . ?
Cd1 O1 2.448(3) 4_565 ?
Cd1 O1 2.448(3) . ?
O1 C11 1.237(5) . ?
N4 C10 1.133(7) . ?
N3 C6 1.376(8) . ?
N3 H3A 0.77(4) . ?
N3 H3A 0.77(4) 4_565 ?
N1 C1 1.412(7) . ?
N1 H1A 0.86(4) . ?
N1 H1A 0.86(4) 4_565 ?
N2 C5 1.144(8) . ?
C10 C9 1.440(7) . ?
C9 C8 1.379(5) 4_565 ?
C9 C8 1.379(5) . ?
C8 C7 1.361(5) . ?
C8 H8 0.9300 . ?
C7 C6 1.381(5) . ?
C7 H7 0.9300 . ?
C1 C2 1.382(5) 4_565 ?
C1 C2 1.382(5) . ?
C2 C3 1.379(6) . ?
C2 H2 0.9300 . ?
C3 C4 1.382(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.425(9) . ?
C11 C12 1.486(10) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C12 H12A 0.96(4) 4_565 ?
C12 H12B 0.96(4) 4_565 ?
C12 H12C 0.9600 4_565 ?
C13 C14 1.499(7) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C14 H14A 0.96(4) 4_565 ?
C14 H14B 0.96(4) 4_565 ?
C14 H14C 0.9600 4_565 ?

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
C13 O2 Cd1 93.6(2) . . ?
C13 O2 Cd1 150.9(2) . 3_756 ?
Cd1 O2 Cd1 110.63(9) . 3_756 ?
N4 Cd1 N1 93.69(17) . . ?
N4 Cd1 O1 91.87(14) . 4_565 ?
N1 Cd1 O1 153.28(7) . 4_565 ?
N4 Cd1 O1 91.87(14) . . ?
N1 Cd1 O1 153.28(7) . . ?
O1 Cd1 O1 52.26(14) 4_565 . ?
N4 Cd1 O2 153.27(6) . 4_565 ?
N1 Cd1 O2 81.83(12) . 4_565 ?
O1 Cd1 O2 81.51(10) 4_565 4_565 ?
O1 Cd1 O2 103.97(10) . 4_565 ?
N4 Cd1 O2 153.27(6) . . ?
N1 Cd1 O2 81.83(12) . . ?
O1 Cd1 O2 103.97(10) 4_565 . ?
O1 Cd1 O2 81.51(10) . . ?
O2 Cd1 O2 52.43(11) 4_565 . ?
N4 Cd1 O2 83.93(6) . 3_756 ?
N1 Cd1 O2 76.60(7) . 3_756 ?
O1 Cd1 O2 130.01(10) 4_565 3_756 ?
O1 Cd1 O2 78.04(10) . 3_756 ?
O2 Cd1 O2 120.03(6) 4_565 3_756 ?
O2 Cd1 O2 69.37(9) . 3_756 ?
N4 Cd1 O2 83.93(6) . 2_756 ?
N1 Cd1 O2 76.60(7) . 2_756 ?
O1 Cd1 O2 78.04(10) 4_565 2_756 ?
O1 Cd1 O2 130.02(10) . 2_756 ?
O2 Cd1 O2 69.37(9) 4_565 2_756 ?
O2 Cd1 O2 120.03(6) . 2_756 ?
O2 Cd1 O2 149.70(14) 3_756 2_756 ?
C11 O1 Cd1 93.1(4) . . ?
C10 N4 Cd1 174.9(5) . . ?
C6 N3 H3A 121(4) . . ?
C6 N3 H3A 121(4) . 4_565 ?
H3A N3 H3A 113(7) . 4_565 ?
C1 N1 Cd1 115.0(3) . . ?
C1 N1 H1A 120(3) . . ?
Cd1 N1 H1A 97(3) . . ?
C1 N1 H1A 120(3) . 4_565 ?
Cd1 N1 H1A 97(3) . 4_565 ?
H1A N1 H1A 104(6) . 4_565 ?
N4 C10 C9 179.8(7) . . ?
C8 C9 C8 118.7(5) 4_565 . ?
C8 C9 C10 120.6(3) 4_565 . ?
C8 C9 C10 120.6(3) . . ?
C7 C8 C9 120.6(4) . . ?
C7 C8 H8 119.7 . . ?
C9 C8 H8 119.7 . . ?
C8 C7 C6 120.9(4) . . ?
C8 C7 H7 119.5 . . ?
C6 C7 H7 119.5 . . ?
N3 C6 C7 120.9(3) . 4_565 ?
N3 C6 C7 120.9(3) . . ?
C7 C6 C7 118.2(5) 4_565 . ?
C2 C1 C2 119.9(5) 4_565 . ?
C2 C1 N1 120.0(3) 4_565 . ?
C2 C1 N1 120.0(3) . . ?
C3 C2 C1 119.9(4) . . ?
C3 C2 H2 120.0 . . ?
C1 C2 H2 120.0 . . ?
C2 C3 C4 120.3(4) . . ?
C2 C3 H3 119.8 . . ?
C4 C3 H3 119.8 . . ?
C3 C4 C3 119.5(5) . 4_565 ?
C3 C4 C5 120.3(3) . . ?
C3 C4 C5 120.3(3) 4_565 . ?
N2 C5 C4 178.8(8) . . ?
O1 C11 O1 121.2(7) 4_565 . ?
O1 C11 C12 119.4(3) 4_565 . ?
O1 C11 C12 119.4(3) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C12 H12A 109.5(9) . 4_565 ?
H12A C12 H12A 55.9 . 4_565 ?
H12B C12 H12A 141.1 . 4_565 ?
H12C C12 H12A 56.6 . 4_565 ?
C11 C12 H12B 109.5(9) . 4_565 ?
H12A C12 H12B 141.1 . 4_565 ?
H12B C12 H12B 56.6 . 4_565 ?
H12C C12 H12B 55.9 . 4_565 ?
H12A C12 H12B 109.5 4_565 4_565 ?
C11 C12 H12C 109.473(7) . 4_565 ?
H12A C12 H12C 56.6 . 4_565 ?
H12B C12 H12C 55.9 . 4_565 ?
H12C C12 H12C 141.1 . 4_565 ?
H12A C12 H12C 109.5 4_565 4_565 ?
H12B C12 H12C 109.5 4_565 4_565 ?
O2 C13 O2 120.4(4) 4_565 . ?
O2 C13 C14 119.8(2) 4_565 . ?
O2 C13 C14 119.8(2) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C14 H14A 109.5(9) . 4_565 ?
H14A C14 H14A 55.3 . 4_565 ?
H14B C14 H14A 141.0 . 4_565 ?
H14C C14 H14A 57.2 . 4_565 ?
C13 C14 H14B 109.5(9) . 4_565 ?
H14A C14 H14B 141.0 . 4_565 ?
H14B C14 H14B 57.2 . 4_565 ?
H14C C14 H14B 55.3 . 4_565 ?
H14A C14 H14B 109.5 4_565 4_565 ?
C13 C14 H14C 109.471(9) . 4_565 ?
H14A C14 H14C 57.2 . 4_565 ?
H14B C14 H14C 55.3 . 4_565 ?
H14C C14 H14C 141.0 . 4_565 ?
H14A C14 H14C 109.5 4_565 4_565 ?
H14B C14 H14C 109.5 4_565 4_565 ?

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
C8 C9 C8 C7 0.1(10) 4_565 . . . ?
C10 C9 C8 C7 -177.4(5) . . . . ?
C9 C8 C7 C6 1.3(9) . . . . ?
C8 C7 C6 N3 -179.9(6) . . . . ?
C8 C7 C6 C7 -2.6(11) . . . 4_565 ?
Cd1 N1 C1 C2 -88.8(4) . . . 4_565 ?
Cd1 N1 C1 C2 88.8(4) . . . . ?
C2 C1 C2 C3 2.2(8) 4_565 . . . ?
N1 C1 C2 C3 -175.4(4) . . . . ?
C1 C2 C3 C4 0.1(7) . . . . ?
C2 C3 C4 C3 -2.3(9) . . . 4_565 ?
C2 C3 C4 C5 178.2(5) . . . . ?
Cd1 O1 C11 O1 -5.1(7) . . . 4_565 ?
Cd1 O1 C11 C12 174.5(6) . . . . ?
Cd1 O2 C13 O2 -1.9(5) . . . 4_565 ?
Cd1 O2 C13 O2 -148.9(2) 3_756 . . 4_565 ?
Cd1 O2 C13 C14 179.8(5) . . . . ?
Cd1 O2 C13 C14 32.7(9) 3_756 . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1A O1 0.86(4) 2.16(4) 3.016(4) 169(4) 3_756
N3 H3A O1 0.77(4) 2.28(4) 3.036(5) 166(5) 3_755

_refine_diff_density_max         0.892
_refine_diff_density_min         -0.966
_refine_diff_density_rms         0.087

####################################################################### 
# 
# 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 2221842'
loop_
_audit_author_name
_audit_author_address
'Behrouz Notash'
;Shahid Beheshti University
Iran
;
_audit_update_record             
;
2022-11-24 deposited with the CCDC.	2023-07-17 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         'C14 H12 Cd N6 O6'
_chemical_formula_sum            'C14 H12 Cd N6 O6'
_chemical_formula_weight         472.71

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cd Cd -0.8075 1.2024 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

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

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

_cell_length_a                   8.0625(16)
_cell_length_b                   11.849(2)
_cell_length_c                   17.831(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1703.4(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    1496
_cell_measurement_theta_min      3.263
_cell_measurement_theta_max      24.996

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.843
_exptl_crystal_F_000             936
_exptl_transmission_factor_min   0.5562
_exptl_transmission_factor_max   0.6912
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.300
_exptl_absorpt_coefficient_mu    1.329
_shelx_estimated_absorpt_T_min   0.556
_shelx_estimated_absorpt_T_max   0.691
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   'shape of crystal determined optically'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'STOE IPDS 2T'
_diffrn_measurement_method       'rotation method'
_diffrn_detector_area_resol_mean '0.15 mm'
_diffrn_reflns_number            4707
_diffrn_reflns_av_unetI/netI     0.0486
_diffrn_reflns_av_R_equivalents  0.0522
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         3.263
_diffrn_reflns_theta_max         24.996
_diffrn_reflns_theta_full        24.996
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             1496
_reflns_number_gt                826
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'X-Area (Stoe & Cie GmbH, 2005)'
_computing_cell_refinement       'X-Area (Stoe & Cie GmbH, 2005)'
_computing_data_reduction        'X-Area (Stoe & Cie GmbH, 2005)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_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)+(0.0867P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1496
_refine_ls_number_parameters     124
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0933
_refine_ls_R_factor_gt           0.0498
_refine_ls_wR_factor_ref         0.1392
_refine_ls_wR_factor_gt          0.1203
_refine_ls_goodness_of_fit_ref   0.948
_refine_ls_restrained_S_all      0.948
_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
Cd1 Cd 1.000000 0.000000 0.500000 0.0335(3) Uani 1 2 d S . P . .
O1 O 1.2111(7) 0.1330(5) 0.4823(3) 0.0655(16) Uani 1 1 d . . . . .
O2 O 1.3376(9) -0.0033(4) 0.4336(3) 0.0759(15) Uani 1 1 d . . . . .
O3 O 1.4504(7) 0.1592(5) 0.4367(3) 0.0665(17) Uani 1 1 d . . . . .
N1 N 0.8315(7) 0.1400(5) 0.4477(3) 0.0340(13) Uani 1 1 d . . . . .
N2 N 0.9946(9) 0.4064(5) 0.1196(3) 0.063(2) Uani 1 1 d . . . . .
N3 N 1.3369(12) 0.0945(6) 0.4501(4) 0.0759(15) Uani 1 1 d . . . . .
C1 C 0.8681(8) 0.1914(5) 0.3767(3) 0.0307(15) Uani 1 1 d . . . . .
C2 C 0.9615(8) 0.2891(6) 0.3749(4) 0.0372(16) Uani 1 1 d . . . . .
H2 H 1.003265 0.318728 0.419343 0.045 Uiso 1 1 calc R U . . .
C3 C 0.8107(9) 0.1448(6) 0.3103(3) 0.0417(17) Uani 1 1 d . . . . .
H3 H 0.750468 0.077841 0.311074 0.050 Uiso 1 1 calc R U . . .
C4 C 0.9933(8) 0.3431(6) 0.3082(4) 0.0397(16) Uani 1 1 d . . . . .
H4 H 1.055185 0.409362 0.307696 0.048 Uiso 1 1 calc R U . . .
C5 C 0.8432(9) 0.1979(6) 0.2433(4) 0.0396(16) Uani 1 1 d . . . . .
H5 H 0.805102 0.166343 0.198795 0.048 Uiso 1 1 calc R U . . .
C6 C 0.9324(9) 0.2984(6) 0.2413(3) 0.0353(15) Uani 1 1 d . . . . .
C7 C 0.9667(10) 0.3576(6) 0.1727(4) 0.048(2) Uani 1 1 d . . . . .
H1A H 0.751(10) 0.115(7) 0.440(4) 0.058 Uiso 1 1 d . U . . .
H1B H 0.805(10) 0.195(7) 0.476(5) 0.058 Uiso 1 1 d . U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cd1 N1 2.338(6) 5_756 ?
Cd1 N1 2.338(6) . ?
Cd1 O1 2.341(6) 5_756 ?
Cd1 O1 2.341(6) . ?
Cd1 N2 2.405(5) 7_566 ?
Cd1 N2 2.405(5) 3_745 ?
O1 N3 1.252(9) . ?
O2 N3 1.196(7) . ?
O3 N3 1.218(9) . ?
N1 C1 1.437(8) . ?
N1 H1A 0.73(8) . ?
N1 H1B 0.85(8) . ?
N2 C7 1.131(9) . ?
C1 C2 1.382(8) . ?
C1 C3 1.385(9) . ?
C2 C4 1.374(9) . ?
C2 H2 0.9300 . ?
C3 C5 1.376(9) . ?
C3 H3 0.9300 . ?
C4 C6 1.394(9) . ?
C4 H4 0.9300 . ?
C5 C6 1.391(10) . ?
C5 H5 0.9300 . ?
C6 C7 1.438(9) . ?

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 Cd1 N1 180.0 5_756 . ?
N1 Cd1 O1 83.8(2) 5_756 5_756 ?
N1 Cd1 O1 96.2(2) . 5_756 ?
N1 Cd1 O1 96.2(2) 5_756 . ?
N1 Cd1 O1 83.8(2) . . ?
O1 Cd1 O1 180.0(2) 5_756 . ?
N1 Cd1 N2 89.1(2) 5_756 7_566 ?
N1 Cd1 N2 90.9(2) . 7_566 ?
O1 Cd1 N2 100.3(2) 5_756 7_566 ?
O1 Cd1 N2 79.7(2) . 7_566 ?
N1 Cd1 N2 90.9(2) 5_756 3_745 ?
N1 Cd1 N2 89.1(2) . 3_745 ?
O1 Cd1 N2 79.7(2) 5_756 3_745 ?
O1 Cd1 N2 100.3(2) . 3_745 ?
N2 Cd1 N2 180.0 7_566 3_745 ?
N3 O1 Cd1 113.9(5) . . ?
C1 N1 Cd1 122.2(4) . . ?
C1 N1 H1A 101(7) . . ?
Cd1 N1 H1A 108(6) . . ?
C1 N1 H1B 105(5) . . ?
Cd1 N1 H1B 117(6) . . ?
H1A N1 H1B 102(8) . . ?
C7 N2 Cd1 168.9(7) . 3_755 ?
O2 N3 O3 124.0(9) . . ?
O2 N3 O1 118.0(8) . . ?
O3 N3 O1 118.0(7) . . ?
C2 C1 C3 119.8(6) . . ?
C2 C1 N1 119.2(6) . . ?
C3 C1 N1 121.1(6) . . ?
C4 C2 C1 120.8(7) . . ?
C4 C2 H2 119.6 . . ?
C1 C2 H2 119.6 . . ?
C5 C3 C1 119.7(6) . . ?
C5 C3 H3 120.1 . . ?
C1 C3 H3 120.1 . . ?
C2 C4 C6 119.8(6) . . ?
C2 C4 H4 120.1 . . ?
C6 C4 H4 120.1 . . ?
C3 C5 C6 120.8(7) . . ?
C3 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C5 C6 C4 119.1(6) . . ?
C5 C6 C7 122.6(7) . . ?
C4 C6 C7 118.3(6) . . ?
N2 C7 C6 178.4(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
Cd1 O1 N3 O2 -1.5(10) . . . . ?
Cd1 O1 N3 O3 177.8(6) . . . . ?
Cd1 N1 C1 C2 -92.2(6) . . . . ?
Cd1 N1 C1 C3 88.2(6) . . . . ?
C3 C1 C2 C4 2.3(10) . . . . ?
N1 C1 C2 C4 -177.3(6) . . . . ?
C2 C1 C3 C5 -1.8(10) . . . . ?
N1 C1 C3 C5 177.9(6) . . . . ?
C1 C2 C4 C6 -0.7(10) . . . . ?
C1 C3 C5 C6 -0.3(11) . . . . ?
C3 C5 C6 C4 1.9(11) . . . . ?
C3 C5 C6 C7 -178.9(7) . . . . ?
C2 C4 C6 C5 -1.4(10) . . . . ?
C2 C4 C6 C7 179.4(7) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1A O3 0.73(8) 2.48(8) 3.087(8) 142(8) 1_455
N1 H1A O2 0.73(8) 2.71(8) 2.993(8) 106(7) 5_756
N1 H1B O1 0.85(8) 2.30(8) 3.119(8) 162(7) 4_456
C2 H2 O2 0.93 2.48 3.126(9) 126.5 8_865

_refine_diff_density_max         1.223
_refine_diff_density_min         -1.451
_refine_diff_density_rms         0.139

####################################################################### 
# 
# 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 2221844'
loop_
_audit_author_name
_audit_author_address
'Behrouz Notash'
;Shahid Beheshti University
Iran
;
_audit_update_record             
;
2022-11-24 deposited with the CCDC.	2023-07-17 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         'C14 H16 Cd N4 O2, 2(Cl O4)'
_chemical_formula_sum            'C14 H16 Cd Cl2 N4 O10'
_chemical_formula_weight         583.62

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'
Cd Cd -0.8075 1.2024 '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'
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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

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

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

_cell_length_a                   7.9310(16)
_cell_length_b                   8.7815(18)
_cell_length_c                   9.6095(19)
_cell_angle_alpha                102.03(3)
_cell_angle_beta                 108.05(3)
_cell_angle_gamma                112.01(3)
_cell_volume                     548.5(2)
_cell_formula_units_Z            1
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    1932
_cell_measurement_theta_min      2.398
_cell_measurement_theta_max      25.00

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.767
_exptl_crystal_F_000             290
_exptl_transmission_factor_min   0.5634
_exptl_transmission_factor_max   0.7376
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.250
_exptl_absorpt_coefficient_mu    1.296
_shelx_estimated_absorpt_T_min   0.563
_shelx_estimated_absorpt_T_max   0.738
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   'shape of crystal determined optically'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'STOE IPDS 2T'
_diffrn_measurement_method       'rotation method'
_diffrn_detector_area_resol_mean '0.15 mm'
_diffrn_reflns_number            4053
_diffrn_reflns_av_unetI/netI     0.0575
_diffrn_reflns_av_R_equivalents  0.0795
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.398
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             1932
_reflns_number_gt                1782
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'X-Area (Stoe & Cie GmbH, 2005)'
_computing_cell_refinement       'X-Area (Stoe & Cie GmbH, 2005)'
_computing_data_reduction        'X-Area (Stoe & Cie GmbH, 2005)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_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)+(0.0693P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1932
_refine_ls_number_parameters     156
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0461
_refine_ls_R_factor_gt           0.0428
_refine_ls_wR_factor_ref         0.1055
_refine_ls_wR_factor_gt          0.1042
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.035
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cd1 Cd 0.000000 0.500000 0.500000 0.04559(19) Uani 1 2 d S . P . .
O1 O 0.1516(7) 0.8035(5) 0.6029(6) 0.0788(11) Uani 1 1 d D . . . .
N2 N 0.1540(6) 0.5185(6) 0.3329(5) 0.0639(10) Uani 1 1 d . . . . .
C6 C 0.2463(6) 0.5329(6) 0.1017(5) 0.0454(9) Uani 1 1 d . . . . .
C5 C 0.3238(7) 0.6915(6) 0.0782(5) 0.0516(10) Uani 1 1 d . . . . .
H5 H 0.358095 0.796656 0.153854 0.062 Uiso 1 1 calc R U . . .
C4 C 0.2014(6) 0.3770(6) -0.0090(5) 0.0481(9) Uani 1 1 d . . . . .
H4 H 0.153545 0.271449 0.007743 0.058 Uiso 1 1 calc R U . . .
C7 C 0.2001(6) 0.5278(6) 0.2335(5) 0.0511(10) Uani 1 1 d . . . . .
C2 C 0.2278(6) 0.3789(5) -0.1426(5) 0.0455(9) Uani 1 1 d . . . . .
H2 H 0.198304 0.274380 -0.216409 0.055 Uiso 1 1 calc R U . . .
C3 C 0.3495(7) 0.6925(6) -0.0559(5) 0.0489(9) Uani 1 1 d . . . . .
H3 H 0.401190 0.798228 -0.071777 0.059 Uiso 1 1 calc R U . . .
Cl1 Cl 0.25605(19) 0.10025(16) 0.36255(18) 0.0703(4) Uani 1 1 d . . . . .
O3 O 0.2511(13) -0.0591(9) 0.3737(9) 0.136(2) Uani 1 1 d . . . . .
O5 O 0.0555(9) 0.0597(8) 0.2708(8) 0.127(2) Uani 1 1 d . . . . .
O4 O 0.3689(14) 0.1308(12) 0.2779(13) 0.201(4) Uani 1 1 d . . . . .
O2 O 0.3411(12) 0.2386(13) 0.4907(11) 0.240(7) Uani 1 1 d . . . . .
N1 N 0.3026(5) 0.5326(5) -0.3151(4) 0.0493(8) Uani 1 1 d D . . . .
C1 C 0.2977(5) 0.5340(5) -0.1692(4) 0.0402(8) Uani 1 1 d . . . . .
H1A H 0.342(7) 0.464(5) -0.350(5) 0.048 Uiso 1 1 d D U . . .
H1B H 0.401(5) 0.622(4) -0.312(6) 0.048 Uiso 1 1 d D U . . .
H1D H 0.200(10) 0.866(8) 0.553(7) 0.09(2) Uiso 1 1 d D . . . .
H1C H 0.078(9) 0.838(8) 0.637(8) 0.09(2) Uiso 1 1 d D . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cd1 N2 2.296(4) . ?
Cd1 N2 2.296(4) 2_566 ?
Cd1 O1 2.300(4) . ?
Cd1 O1 2.300(4) 2_566 ?
Cd1 N1 2.373(4) 2_565 ?
Cd1 N1 2.373(4) 1_556 ?
O1 H1D 0.86(2) . ?
O1 H1C 0.87(2) . ?
N2 C7 1.131(6) . ?
C6 C4 1.388(6) . ?
C6 C5 1.395(7) . ?
C6 C7 1.427(5) . ?
C5 C3 1.367(6) . ?
C5 H5 0.9300 . ?
C4 C2 1.366(6) . ?
C4 H4 0.9300 . ?
C2 C1 1.376(6) . ?
C2 H2 0.9300 . ?
C3 C1 1.398(6) . ?
C3 H3 0.9300 . ?
Cl1 O2 1.302(6) . ?
Cl1 O4 1.377(7) . ?
Cl1 O3 1.412(6) . ?
Cl1 O5 1.417(6) . ?
N1 C1 1.412(5) . ?
N1 H1A 0.834(19) . ?
N1 H1B 0.863(19) . ?

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
N2 Cd1 N2 180.0 . 2_566 ?
N2 Cd1 O1 88.89(17) . . ?
N2 Cd1 O1 91.11(17) 2_566 . ?
N2 Cd1 O1 91.11(17) . 2_566 ?
N2 Cd1 O1 88.89(17) 2_566 2_566 ?
O1 Cd1 O1 180.0 . 2_566 ?
N2 Cd1 N1 94.24(13) . 2_565 ?
N2 Cd1 N1 85.76(13) 2_566 2_565 ?
O1 Cd1 N1 94.59(16) . 2_565 ?
O1 Cd1 N1 85.42(16) 2_566 2_565 ?
N2 Cd1 N1 85.76(13) . 1_556 ?
N2 Cd1 N1 94.24(13) 2_566 1_556 ?
O1 Cd1 N1 85.41(16) . 1_556 ?
O1 Cd1 N1 94.58(16) 2_566 1_556 ?
N1 Cd1 N1 180.0 2_565 1_556 ?
Cd1 O1 H1D 121(5) . . ?
Cd1 O1 H1C 110(5) . . ?
H1D O1 H1C 112(6) . . ?
C7 N2 Cd1 167.7(4) . . ?
C4 C6 C5 119.8(4) . . ?
C4 C6 C7 119.6(4) . . ?
C5 C6 C7 120.4(4) . . ?
C3 C5 C6 120.1(4) . . ?
C3 C5 H5 120.0 . . ?
C6 C5 H5 120.0 . . ?
C2 C4 C6 119.8(4) . . ?
C2 C4 H4 120.1 . . ?
C6 C4 H4 120.1 . . ?
N2 C7 C6 176.6(5) . . ?
C4 C2 C1 120.7(4) . . ?
C4 C2 H2 119.7 . . ?
C1 C2 H2 119.7 . . ?
C5 C3 C1 119.7(4) . . ?
C5 C3 H3 120.2 . . ?
C1 C3 H3 120.2 . . ?
O2 Cl1 O4 108.9(7) . . ?
O2 Cl1 O3 119.3(7) . . ?
O4 Cl1 O3 99.1(5) . . ?
O2 Cl1 O5 111.3(4) . . ?
O4 Cl1 O5 110.7(6) . . ?
O3 Cl1 O5 106.8(4) . . ?
C1 N1 Cd1 112.6(2) . 1_554 ?
C1 N1 H1A 113(3) . . ?
Cd1 N1 H1A 114(3) 1_554 . ?
C1 N1 H1B 116(3) . . ?
Cd1 N1 H1B 108(3) 1_554 . ?
H1A N1 H1B 91(4) . . ?
C2 C1 C3 119.9(4) . . ?
C2 C1 N1 120.5(4) . . ?
C3 C1 N1 119.4(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
C4 C6 C5 C3 2.1(6) . . . . ?
C7 C6 C5 C3 -173.7(4) . . . . ?
C5 C6 C4 C2 -1.9(6) . . . . ?
C7 C6 C4 C2 173.9(4) . . . . ?
C6 C4 C2 C1 -0.3(6) . . . . ?
C6 C5 C3 C1 0.0(7) . . . . ?
C4 C2 C1 C3 2.4(6) . . . . ?
C4 C2 C1 N1 -172.6(4) . . . . ?
C5 C3 C1 C2 -2.2(6) . . . . ?
C5 C3 C1 N1 172.8(4) . . . . ?
Cd1 N1 C1 C2 89.7(4) 1_554 . . . ?
Cd1 N1 C1 C3 -85.3(4) 1_554 . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1A O2 0.834(19) 2.23(2) 3.029(7) 160(4) 1_554
N1 H1B O4 0.863(19) 2.12(2) 2.977(9) 170(4) 2_665
O1 H1C O5 0.87(2) 1.91(2) 2.779(7) 173(7) 2_566
O1 H1D O3 0.86(2) 2.07(3) 2.899(9) 162(7) 1_565

_refine_diff_density_max         0.735
_refine_diff_density_min         -0.933
_refine_diff_density_rms         0.126

