# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2018

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

data_1_4_CuCl2_2
_database_code_depnum_ccdc_archive 'CCDC 1821327'
_audit_update_record             
;
2018-02-01 deposited with the CCDC.
2018-03-02 downloaded from the CCDC.
;
_audit_creation_date             2018-01-23
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.07.20 svn.r3457 for OlexSys, GUI svn.r5370)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C20 H12 Cl8 Cu2 F4 N4'
_chemical_formula_sum            'C20 H12 Cl8 Cu2 F4 N4'
_chemical_formula_weight         795.02
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'
F F 0.0171 0.0103 '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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.4310(15)
_cell_length_b                   8.7786(18)
_cell_length_c                   10.589(2)
_cell_angle_alpha                87.15(3)
_cell_angle_beta                 82.23(3)
_cell_angle_gamma                82.29(3)
_cell_volume                     677.9(2)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    1307
_cell_measurement_temperature    170.0(1)
_cell_measurement_theta_max      27.878
_cell_measurement_theta_min      0.407
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.405
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6085
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2012/1 (Bruker,2012) was used for absorption correction. wR2(int) was 0.0662 before and 0.0552 after correction. The Ratio of minimum to maximum transmission is 0.8160. The λ/2 correction factor is 0.0015.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            green
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.947
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             390
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.11
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0299
_diffrn_reflns_av_unetI/netI     0.0611
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            4433
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.249
_diffrn_reflns_theta_min         2.342
_diffrn_ambient_temperature      170.0(1)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1968
_reflns_number_total             2443
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.438
_refine_diff_density_min         -0.561
_refine_diff_density_rms         0.108
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2443
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0559
_refine_ls_R_factor_gt           0.0406
_refine_ls_restrained_S_all      1.063
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+1.4938P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0825
_refine_ls_wR_factor_ref         0.0887
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C3'(H3'), C4(H4), C4'(H4'), C6(H6), C6'(H6')
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.37712(7) 0.61600(5) 0.38392(5) 0.01678(15) Uani 1 1 d . . . . .
Cl1 Cl 0.12591(13) 0.63359(12) 0.28480(10) 0.0229(3) Uani 1 1 d . . . . .
Cl1' Cl 0.64474(13) 0.63287(11) 0.46778(9) 0.0176(2) Uani 1 1 d . . . . .
Cl2 Cl 0.65610(16) 0.74950(13) 0.14585(11) 0.0307(3) Uani 1 1 d . . . . .
Cl2' Cl 0.37580(14) 0.97241(12) 0.37628(10) 0.0222(2) Uani 1 1 d . . . . .
F5 F 0.5691(4) 0.1117(3) 0.1252(2) 0.0399(7) Uani 1 1 d . . . . .
F5' F -0.0820(3) 0.7492(3) 0.8075(2) 0.0328(6) Uani 1 1 d . . . . .
N1 N 0.5253(4) 0.4966(4) 0.2323(3) 0.0180(8) Uani 1 1 d . . . . .
N1' N 0.2316(4) 0.7586(4) 0.5198(3) 0.0185(8) Uani 1 1 d . . . . .
C2 C 0.6380(6) 0.5556(5) 0.1403(4) 0.0204(9) Uani 1 1 d . . . . .
C2' C 0.2469(5) 0.9081(5) 0.5116(4) 0.0181(9) Uani 1 1 d . . . . .
C3 C 0.7358(6) 0.4741(5) 0.0387(4) 0.0260(10) Uani 1 1 d . . . . .
H3 H 0.8137 0.5205 -0.0232 0.031 Uiso 1 1 calc R . . . .
C3' C 0.1619(6) 1.0138(5) 0.6024(4) 0.0218(10) Uani 1 1 d . . . . .
H3' H 0.1794 1.1169 0.5942 0.026 Uiso 1 1 calc R . . . .
C4 C 0.7126(6) 0.3208(5) 0.0332(4) 0.0282(11) Uani 1 1 d . . . . .
H4 H 0.7747 0.2604 -0.0326 0.034 Uiso 1 1 calc R . . . .
C4' C 0.0505(5) 0.9586(5) 0.7052(4) 0.0213(10) Uani 1 1 d . . . . .
H4' H -0.0084 1.0234 0.7691 0.026 Uiso 1 1 calc R . . . .
C5 C 0.5958(6) 0.2611(5) 0.1274(4) 0.0262(10) Uani 1 1 d . . . . .
C5' C 0.0294(6) 0.8046(5) 0.7101(4) 0.0240(10) Uani 1 1 d . . . . .
C6 C 0.5018(6) 0.3485(5) 0.2250(4) 0.0210(9) Uani 1 1 d . . . . .
H6 H 0.4211 0.3047 0.2866 0.025 Uiso 1 1 calc R . . . .
C6' C 0.1198(5) 0.7059(5) 0.6188(4) 0.0199(9) Uani 1 1 d . . . . .
H6' H 0.1039 0.6024 0.6252 0.024 Uiso 1 1 calc R . . . .


_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 Cl1 2.2464(12) . ?
Cu1 Cl1' 2.6364(13) 2_666 ?
Cu1 Cl1' 2.3097(12) . ?
Cu1 N1 2.066(3) . ?
Cu1 N1' 2.050(3) . ?
Cl1' Cu1 2.6364(13) 2_666 ?
Cl2 C2 1.730(4) . ?
Cl2' C2' 1.727(4) . ?
F5 C5 1.355(5) . ?
F5' C5' 1.347(5) . ?
N1 C2 1.328(5) . ?
N1 C6 1.342(5) . ?
N1' C2' 1.330(5) . ?
N1' C6' 1.350(5) . ?
C2 C3 1.387(6) . ?
C2' C3' 1.397(6) . ?
C3 H3 0.9300 . ?
C3 C4 1.384(6) . ?
C3' H3' 0.9300 . ?
C3' C4' 1.384(6) . ?
C4 H4 0.9300 . ?
C4 C5 1.364(6) . ?
C4' H4' 0.9300 . ?
C4' C5' 1.379(6) . ?
C5 C6 1.372(6) . ?
C5' C6' 1.374(6) . ?
C6 H6 0.9300 . ?
C6' H6' 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
Cl1 Cu1 Cl1' 103.53(5) . 2_666 ?
Cl1 Cu1 Cl1' 170.99(5) . . ?
Cl1' Cu1 Cl1' 85.49(5) . 2_666 ?
N1 Cu1 Cl1 89.46(10) . . ?
N1 Cu1 Cl1' 93.66(10) . 2_666 ?
N1 Cu1 Cl1' 90.07(10) . . ?
N1' Cu1 Cl1 88.72(10) . . ?
N1' Cu1 Cl1' 90.64(10) . . ?
N1' Cu1 Cl1' 93.51(10) . 2_666 ?
N1' Cu1 N1 172.83(14) . . ?
Cu1 Cl1' Cu1 94.51(5) . 2_666 ?
C2 N1 Cu1 125.3(3) . . ?
C2 N1 C6 117.6(4) . . ?
C6 N1 Cu1 117.1(3) . . ?
C2' N1' Cu1 119.6(3) . . ?
C2' N1' C6' 118.2(3) . . ?
C6' N1' Cu1 122.1(3) . . ?
N1 C2 Cl2 117.1(3) . . ?
N1 C2 C3 124.6(4) . . ?
C3 C2 Cl2 118.3(4) . . ?
N1' C2' Cl2' 116.4(3) . . ?
N1' C2' C3' 124.2(4) . . ?
C3' C2' Cl2' 119.3(3) . . ?
C2 C3 H3 121.4 . . ?
C4 C3 C2 117.2(4) . . ?
C4 C3 H3 121.4 . . ?
C2' C3' H3' 121.4 . . ?
C4' C3' C2' 117.2(4) . . ?
C4' C3' H3' 121.4 . . ?
C3 C4 H4 121.0 . . ?
C5 C4 C3 118.0(4) . . ?
C5 C4 H4 121.0 . . ?
C3' C4' H4' 121.0 . . ?
C5' C4' C3' 118.0(4) . . ?
C5' C4' H4' 121.0 . . ?
F5 C5 C4 119.7(4) . . ?
F5 C5 C6 118.4(4) . . ?
C4 C5 C6 121.9(4) . . ?
F5' C5' C4' 119.1(4) . . ?
F5' C5' C6' 119.1(4) . . ?
C6' C5' C4' 121.9(4) . . ?
N1 C6 C5 120.6(4) . . ?
N1 C6 H6 119.7 . . ?
C5 C6 H6 119.7 . . ?
N1' C6' C5' 120.3(4) . . ?
N1' C6' H6' 119.9 . . ?
C5' C6' H6' 119.9 . . ?

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

data_2_4_CuCl2_2
_database_code_depnum_ccdc_archive 'CCDC 1821328'
_audit_update_record             
;
2018-02-01 deposited with the CCDC.
2018-03-02 downloaded from the CCDC.
;
_audit_creation_date             2018-01-23
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.07.20 svn.r3457 for OlexSys, GUI svn.r5370)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H12 Cl12 Cu2 N4'
_chemical_formula_sum            'C20 H12 Cl12 Cu2 N4'
_chemical_formula_weight         860.82
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'I 1 2/a 1'
_space_group_name_Hall           '-I 2ya'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'x, -y+1/2, z+1/2'

_cell_length_a                   14.396(3)
_cell_length_b                   14.183(3)
_cell_length_c                   15.458(3)
_cell_angle_alpha                90
_cell_angle_beta                 114.23(3)
_cell_angle_gamma                90
_cell_volume                     2878.2(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3246
_cell_measurement_temperature    170.0(1)
_cell_measurement_theta_max      27.878
_cell_measurement_theta_min      0.407
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.614
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6190
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2012/1 (Bruker,2012) was used for absorption correction. wR2(int) was 0.0594 before and 0.0472 after correction. The Ratio of minimum to maximum transmission is 0.8301. The λ/2 correction factor is 0.0015.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            green
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.987
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1688
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.19
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0219
_diffrn_reflns_av_unetI/netI     0.0256
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            7740
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.247
_diffrn_reflns_theta_min         2.114
_diffrn_ambient_temperature      170.0(1)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2338
_reflns_number_total             2582
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.364
_refine_diff_density_min         -0.284
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2582
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0237
_refine_ls_R_factor_gt           0.0202
_refine_ls_restrained_S_all      1.037
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0197P)²+3.8531P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0503
_refine_ls_wR_factor_ref         0.0520
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C3'(H3'), C4(H4), C4'(H4'), C6(H6), C6'(H6')
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.36159(2) 0.58075(2) 0.61206(2) 0.01657(8) Uani 1 1 d . . . . .
Cl1 Cl 0.53147(4) 0.58138(3) 0.66253(3) 0.02404(12) Uani 1 1 d . . . . .
Cl1' Cl 0.18995(3) 0.58523(3) 0.57420(3) 0.01803(11) Uani 1 1 d . . . . .
Cl2 Cl 0.33382(5) 0.45030(4) 0.77461(3) 0.03251(14) Uani 1 1 d . . . . .
Cl2' Cl 0.37341(4) 0.68635(3) 0.79934(3) 0.02445(12) Uani 1 1 d . . . . .
Cl5 Cl 0.40358(4) 0.22569(4) 0.46712(4) 0.03016(13) Uani 1 1 d . . . . .
Cl5' Cl 0.38167(4) 0.95123(4) 0.48878(3) 0.02907(13) Uani 1 1 d . . . . .
N1 N 0.36346(12) 0.43445(11) 0.61901(10) 0.0195(4) Uani 1 1 d . . . . .
N1' N 0.36811(11) 0.72425(11) 0.63207(10) 0.0168(3) Uani 1 1 d . . . . .
C2 C 0.35173(15) 0.38597(15) 0.68803(13) 0.0212(4) Uani 1 1 d . . . . .
C2' C 0.37391(14) 0.76294(14) 0.71288(13) 0.0185(4) Uani 1 1 d . . . . .
C3 C 0.35573(16) 0.28895(15) 0.69532(14) 0.0255(5) Uani 1 1 d . . . . .
H3 H 0.3480 0.2586 0.7453 0.031 Uiso 1 1 calc R . . . .
C3' C 0.38165(15) 0.85858(14) 0.73112(13) 0.0214(4) Uani 1 1 d . . . . .
H3' H 0.3850 0.8820 0.7885 0.026 Uiso 1 1 calc R . . . .
C4 C 0.37150(15) 0.23825(15) 0.62662(14) 0.0245(5) Uani 1 1 d . . . . .
H4 H 0.3738 0.1727 0.6285 0.029 Uiso 1 1 calc R . . . .
C4' C 0.38420(16) 0.91822(14) 0.66181(14) 0.0225(4) Uani 1 1 d . . . . .
H4' H 0.3894 0.9831 0.6710 0.027 Uiso 1 1 calc R . . . .
C5 C 0.38382(15) 0.28724(14) 0.55478(13) 0.0214(4) Uani 1 1 d . . . . .
C5' C 0.37885(14) 0.87848(14) 0.57786(13) 0.0194(4) Uani 1 1 d . . . . .
C6 C 0.38143(14) 0.38426(14) 0.55294(13) 0.0202(4) Uani 1 1 d . . . . .
H6 H 0.3924 0.4160 0.5053 0.024 Uiso 1 1 calc R . . . .
C6' C 0.37121(14) 0.78275(14) 0.56453(13) 0.0186(4) Uani 1 1 d . . . . .
H6' H 0.3681 0.7577 0.5078 0.022 Uiso 1 1 calc R . . . .


_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 Cl1 2.2413(8) . ?
Cu1 Cl1' 2.6629(8) 2_556 ?
Cu1 Cl1' 2.2946(8) . ?
Cu1 N1 2.0773(17) . ?
Cu1 N1' 2.0550(17) . ?
Cl1' Cu1 2.6629(8) 2_556 ?
Cl2 C2 1.724(2) . ?
Cl2' C2' 1.7247(19) . ?
Cl5 C5 1.731(2) . ?
Cl5' C5' 1.7344(19) . ?
N1 C2 1.337(2) . ?
N1 C6 1.354(2) . ?
N1' C2' 1.335(2) . ?
N1' C6' 1.349(2) . ?
C2 C3 1.380(3) . ?
C2' C3' 1.381(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.376(3) . ?
C3' H3' 0.9300 . ?
C3' C4' 1.377(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.382(3) . ?
C4' H4' 0.9300 . ?
C4' C5' 1.388(3) . ?
C5 C6 1.376(3) . ?
C5' C6' 1.371(3) . ?
C6 H6 0.9300 . ?
C6' H6' 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
Cl1 Cu1 Cl1' 99.00(4) . 2_556 ?
Cl1 Cu1 Cl1' 174.634(19) . . ?
Cl1' Cu1 Cl1' 86.01(4) . 2_556 ?
N1 Cu1 Cl1 89.82(5) . . ?
N1 Cu1 Cl1' 94.11(4) . 2_556 ?
N1 Cu1 Cl1' 91.75(5) . . ?
N1' Cu1 Cl1 88.15(4) . . ?
N1' Cu1 Cl1' 89.36(4) . . ?
N1' Cu1 Cl1' 96.57(4) . 2_556 ?
N1' Cu1 N1 169.32(6) . . ?
Cu1 Cl1' Cu1 93.91(4) . 2_556 ?
C2 N1 Cu1 123.49(13) . . ?
C2 N1 C6 117.22(17) . . ?
C6 N1 Cu1 119.25(13) . . ?
C2' N1' Cu1 121.96(13) . . ?
C2' N1' C6' 117.53(16) . . ?
C6' N1' Cu1 120.45(12) . . ?
N1 C2 Cl2 117.09(15) . . ?
N1 C2 C3 124.28(18) . . ?
C3 C2 Cl2 118.60(15) . . ?
N1' C2' Cl2' 116.58(15) . . ?
N1' C2' C3' 124.32(17) . . ?
C3' C2' Cl2' 119.09(14) . . ?
C2 C3 H3 120.9 . . ?
C4 C3 C2 118.20(18) . . ?
C4 C3 H3 120.9 . . ?
C2' C3' H3' 121.0 . . ?
C4' C3' C2' 118.04(17) . . ?
C4' C3' H3' 121.0 . . ?
C3 C4 H4 120.9 . . ?
C3 C4 C5 118.27(19) . . ?
C5 C4 H4 120.9 . . ?
C3' C4' H4' 121.0 . . ?
C3' C4' C5' 117.97(18) . . ?
C5' C4' H4' 121.0 . . ?
C4 C5 Cl5 119.48(16) . . ?
C6 C5 Cl5 119.92(15) . . ?
C6 C5 C4 120.59(18) . . ?
C4' C5' Cl5' 119.37(15) . . ?
C6' C5' Cl5' 119.76(14) . . ?
C6' C5' C4' 120.87(17) . . ?
N1 C6 C5 121.39(18) . . ?
N1 C6 H6 119.3 . . ?
C5 C6 H6 119.3 . . ?
N1' C6' C5' 121.27(17) . . ?
N1' C6' H6' 119.4 . . ?
C5' C6' H6' 119.4 . . ?

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

data_7_2_CuCl2
_database_code_depnum_ccdc_archive 'CCDC 1821335'
_audit_update_record             
;
2018-02-01 deposited with the CCDC.
2018-03-02 downloaded from the CCDC.
;
_audit_creation_date             2018-01-23
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.07.20 svn.r3457 for OlexSys, GUI svn.r5370)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C10 H6 Br4 Cl2 Cu N2'
_chemical_formula_sum            'C10 H6 Br4 Cl2 Cu N2'
_chemical_formula_weight         608.25
_chemical_melting_point          ?
_chemical_oxdiff_formula         CuCl2Br2C10H8N2
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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
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                   8.2021(4)
_cell_length_b                   12.8425(7)
_cell_length_c                   14.6338(6)
_cell_angle_alpha                90
_cell_angle_beta                 91.109(5)
_cell_angle_gamma                90
_cell_volume                     1541.17(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3748
_cell_measurement_temperature    120.00(10)
_cell_measurement_theta_max      76.0700
_cell_measurement_theta_min      6.0540
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    17.233
_exptl_absorpt_correction_T_max  0.707
_exptl_absorpt_correction_T_min  0.467
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            green
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    2.621
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1132
_exptl_crystal_size_max          0.0996
_exptl_crystal_size_mid          0.0669
_exptl_crystal_size_min          0.0383
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0602
_diffrn_reflns_av_unetI/netI     0.0359
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            6858
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        66.745
_diffrn_reflns_theta_max         66.745
_diffrn_reflns_theta_min         6.049
_diffrn_ambient_temperature      120.00(10)
_diffrn_detector_area_resol_mean 10.3953
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -34.00   33.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      -41.6513   37.0000   60.0000 67

#__ type_ start__ end____ width___ exp.time_
  2 omega  -66.00  -16.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      -41.6513   37.0000  -30.0000 50

#__ type_ start__ end____ width___ exp.time_
  3 omega  -93.00   -2.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      -41.6513  125.0000  150.0000 91

#__ type_ start__ end____ width___ exp.time_
  4 omega    6.00   31.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       41.6513  -99.0000  150.0000 25

#__ type_ start__ end____ width___ exp.time_
  5 omega    1.00   59.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       41.6513  -99.0000   90.0000 58

#__ type_ start__ end____ width___ exp.time_
  6 omega   60.00  114.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -111.0000   30.0000 54

#__ type_ start__ end____ width___ exp.time_
  7 omega   75.00  107.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -77.0000   60.0000 32

#__ type_ start__ end____ width___ exp.time_
  8 omega   85.00  121.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -35.0000   24.3765 36

#__ type_ start__ end____ width___ exp.time_
  9 omega   89.00  134.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   45.0000  120.0000 45

#__ type_ start__ end____ width___ exp.time_
 10 omega  125.00  177.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   15.0000  150.0000 52

#__ type_ start__ end____ width___ exp.time_
 11 omega  151.00  176.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   45.0000   60.0000 25

#__ type_ start__ end____ width___ exp.time_
 12 omega  118.00  143.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  111.0000    0.0000 25

#__ type_ start__ end____ width___ exp.time_
 13 omega  119.00  145.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  178.0000    0.0000 26

#__ type_ start__ end____ width___ exp.time_
 14 omega  153.00  178.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  111.0000 -120.0000 25

#__ type_ start__ end____ width___ exp.time_
 15 omega  104.00  157.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -15.0000 -120.0000 53

#__ type_ start__ end____ width___ exp.time_
 16 omega   73.00  114.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -111.0000  -60.0000 41

#__ type_ start__ end____ width___ exp.time_
 17 omega   66.00  115.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -111.0000 -150.0000 49

#__ type_ start__ end____ width___ exp.time_
 18 omega   64.00  113.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -111.0000 -180.0000 49

#__ type_ start__ end____ width___ exp.time_
 19 omega   60.00  135.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -61.0000  -60.0000 75

#__ type_ start__ end____ width___ exp.time_
 20 omega   69.00  112.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -111.0000   90.0000 43

#__ type_ start__ end____ width___ exp.time_
 21 omega   84.00  112.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -77.0000  150.0000 28

#__ type_ start__ end____ width___ exp.time_
 22 omega   52.00   79.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -94.0000   30.0000 27

#__ type_ start__ end____ width___ exp.time_
 23 omega   38.00  138.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000  120.0000 100

#__ type_ start__ end____ width___ exp.time_
 24 omega   89.00  139.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   45.0000   60.0000 50

#__ type_ start__ end____ width___ exp.time_
 25 omega   75.00  102.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   15.0000  150.0000 27

#__ type_ start__ end____ width___ exp.time_
 26 omega   38.00   67.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -77.0000  150.0000 29

#__ type_ start__ end____ width___ exp.time_
 27 omega   36.00   63.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -111.0000  150.0000 27

#__ type_ start__ end____ width___ exp.time_
 28 omega   42.00   72.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -35.0000   24.3765 30

#__ type_ start__ end____ width___ exp.time_
 29 omega   45.00   72.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -61.0000  -90.0000 27

#__ type_ start__ end____ width___ exp.time_
 30 omega   40.00   67.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000 -120.0000 27

#__ type_ start__ end____ width___ exp.time_
 31 omega   49.00  126.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -45.0000 -150.0000 77

#__ type_ start__ end____ width___ exp.time_
 32 omega   44.00   84.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -61.0000 -180.0000 40

#__ type_ start__ end____ width___ exp.time_
 33 omega   42.00   95.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -77.0000  -90.0000 53

#__ type_ start__ end____ width___ exp.time_
 34 omega   30.00  100.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -15.0000 -120.0000 70

#__ type_ start__ end____ width___ exp.time_
 35 omega   63.00  150.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  178.0000   90.0000 87

#__ type_ start__ end____ width___ exp.time_
 36 omega -113.00  -14.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      -41.6513  -57.0000  -60.0000 99
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0086339000
_diffrn_orient_matrix_UB_12      0.1180695000
_diffrn_orient_matrix_UB_13      -0.0175717000
_diffrn_orient_matrix_UB_21      0.1876065000
_diffrn_orient_matrix_UB_22      -0.0048926000
_diffrn_orient_matrix_UB_23      0.0057646000
_diffrn_orient_matrix_UB_31      0.0052107000
_diffrn_orient_matrix_UB_32      -0.0203881000
_diffrn_orient_matrix_UB_33      -0.1036854000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1258
_reflns_number_total             1364
_reflns_odcompleteness_completeness 98.90
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     77.49
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.888
_refine_diff_density_min         -0.780
_refine_diff_density_rms         0.208
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     87
_refine_ls_number_reflns         1364
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0446
_refine_ls_R_factor_gt           0.0419
_refine_ls_restrained_S_all      1.077
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0736P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1009
_refine_ls_wR_factor_ref         0.1032
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br2 Br 0.64628(6) 0.91992(4) 0.65281(3) 0.0262(2) Uani 1 1 d . . . . .
Br5 Br 0.34108(6) 0.55970(4) 0.39182(3) 0.0241(2) Uani 1 1 d . . . . .
Cu1 Cu 0.5000 0.70791(7) 0.7500 0.0180(3) Uani 1 2 d S T P . .
Cl1 Cl 0.24516(12) 0.64611(9) 0.75814(7) 0.0221(3) Uani 1 1 d . . . . .
N1 N 0.4864(4) 0.7346(3) 0.6141(2) 0.0181(7) Uani 1 1 d . . . . .
C2 C 0.5573(5) 0.8163(4) 0.5744(3) 0.0210(9) Uani 1 1 d . . . . .
C3 C 0.5646(6) 0.8305(4) 0.4811(3) 0.0238(9) Uani 1 1 d . . . . .
H3 H 0.6112 0.8901 0.4567 0.029 Uiso 1 1 calc R . . . .
C4 C 0.5000(6) 0.7531(4) 0.4244(3) 0.0229(9) Uani 1 1 d . . . . .
H4 H 0.5060 0.7581 0.3611 0.027 Uiso 1 1 calc R . . . .
C5 C 0.4267(5) 0.6684(4) 0.4652(3) 0.0198(8) Uani 1 1 d . . . . .
C6 C 0.4200(5) 0.6609(4) 0.5591(3) 0.0198(8) Uani 1 1 d . . . . .
H6 H 0.3687 0.6039 0.5851 0.024 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br2 C2 1.894(4) . ?
Br5 C5 1.889(4) . ?
Cu1 Cl1 2.2412(11) . ?
Cu1 Cl1 2.2411(11) 2_656 ?
Cu1 N1 2.019(3) . ?
Cu1 N1 2.019(3) 2_656 ?
N1 C2 1.338(6) . ?
N1 C6 1.350(6) . ?
C2 C3 1.380(6) . ?
C3 H3 0.9300 . ?
C3 C4 1.393(7) . ?
C4 H4 0.9300 . ?
C4 C5 1.383(7) . ?
C5 C6 1.379(6) . ?
C6 H6 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
Cl1 Cu1 Cl1 138.51(7) 2_656 . ?
N1 Cu1 Cl1 94.51(11) . . ?
N1 Cu1 Cl1 94.51(11) 2_656 2_656 ?
N1 Cu1 Cl1 92.38(11) . 2_656 ?
N1 Cu1 Cl1 92.38(11) 2_656 . ?
N1 Cu1 N1 160.5(2) . 2_656 ?
C2 N1 Cu1 123.0(3) . . ?
C2 N1 C6 117.7(4) . . ?
C6 N1 Cu1 118.9(3) . . ?
N1 C2 Br2 116.9(3) . . ?
N1 C2 C3 124.1(4) . . ?
C3 C2 Br2 118.9(4) . . ?
C2 C3 H3 120.9 . . ?
C2 C3 C4 118.2(4) . . ?
C4 C3 H3 120.9 . . ?
C3 C4 H4 121.1 . . ?
C5 C4 C3 117.8(4) . . ?
C5 C4 H4 121.1 . . ?
C4 C5 Br5 119.7(3) . . ?
C6 C5 Br5 119.6(4) . . ?
C6 C5 C4 120.8(4) . . ?
N1 C6 C5 121.4(4) . . ?
N1 C6 H6 119.3 . . ?
C5 C6 H6 119.3 . . ?

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-1 -8 -4 0.0346 -0.8775 -8.0532 -3.6164 -0.8949 -0.1461 0.5346
5 -3 -3 0.0213 5.1102 -3.0121 -3.2196 -0.2549 0.9549 0.4219
-5 3 1 0.0286 -5.0583 2.9909 1.2173 0.2881 -0.9566 -0.2136
5 -2 3 0.0183 4.9521 -1.9480 2.7238 -0.2351 0.9543 -0.2169
-5 2 -3 0.0199 -4.9521 1.9480 -2.7238 0.2351 -0.9543 0.2169
0 -5 7 0.0398 -0.1701 -4.9287 7.3250 -0.7121 0.0344 -0.6599
0 5 -7 0.0336 0.1701 4.9287 -7.3250 0.7121 -0.0344 0.6599
1 8 4 0.0323 0.8775 8.0532 3.6164 0.8949 0.1461 -0.5346

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

data_3FPy_2_CuCl2
_database_code_depnum_ccdc_archive 'CCDC 1821337'
_audit_update_record             
;
2018-02-01 deposited with the CCDC.
2018-03-02 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_DIFMN02_3FPy_2_CuCl2        
;
PROBLEM: The minimum difference density is < -0.1*ZMAX*1.00
RESPONSE: Due to unresolved disorder and twinning
;
_vrf_PLAT097_3FPy_2_CuCl2        
;
PROBLEM: Large Reported Max.  (Positive) Residual Density       5.35 eA-3  
RESPONSE: Due to unresolved disorder and twinning
;
_vrf_PLAT098_3FPy_2_CuCl2        
;
PROBLEM: Large Reported Min.  (Negative) Residual Density      -4.50 eA-3  
RESPONSE: Due to unresolved disorder and twinning
;
# end Validation Reply Form
_audit_creation_date             2018-01-23
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.07.20 svn.r3457 for OlexSys, GUI svn.r5370)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C10 H8 Cl2 Cu F2 N2'
_chemical_formula_sum            'C10 H8 Cl2 Cu F2 N2'
_chemical_formula_weight         328.62
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C20 H20 N2 Cu1 F1 Cl1'
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'
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'
F F 0.0171 0.0103 '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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   3.72080(10)
_cell_length_b                   15.9058(5)
_cell_length_c                   11.7364(5)
_cell_angle_alpha                90
_cell_angle_beta                 94.532(3)
_cell_angle_gamma                90
_cell_volume                     692.42(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2332
_cell_measurement_temperature    120.0(1)
_cell_measurement_theta_max      27.4540
_cell_measurement_theta_min      3.6940
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.964
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.92486
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            blue
_exptl_crystal_colour_primary    blue
_exptl_crystal_density_diffrn    1.576
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             326
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -13 13 0.0147
0 12 -14 0.0132
4 12 6 0.0931
-4 -12 -6 0.0916
0 14 13 0.0180
1 -9 -15 0.0068
-1 3 16 0.0309
0 -14 -13 0.0066

_exptl_crystal_size_max          0.257
_exptl_crystal_size_mid          0.037
_exptl_crystal_size_min          0.025
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0.0018 -13.0040 12.9986 -0.1572 -0.4345 0.8623
-0.0019 12.0044 -13.9983 0.1203 0.5001 -0.8615
4.0014 11.9968 5.9997 -0.2375 -0.8833 -0.4598
-4.0014 -11.9968 -5.9997 0.2375 0.8833 0.4598
0.0019 13.9943 12.9960 0.5038 -0.8687 -0.0451
0.9980 -8.9939 -14.9956 -0.5576 0.7890 -0.2516
-0.9979 2.9939 15.9959 0.4231 -0.7420 0.4860
-0.0019 -13.9943 -12.9960 -0.5038 0.8687 0.0451

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_av_unetI/netI     0.0430
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -1
_diffrn_reflns_number            1216
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         3.097
_diffrn_ambient_temperature      120.0(1)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0107
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -88.00  10.00   2.00  115.00    --  -18.14 -77.00 150.00   49
  2  ω    -87.00   3.00   2.00  115.00    --  -18.14 -57.00   0.00   45
  3  ω    -90.00 -62.00   2.00  115.00    --  -18.14 148.00 -25.97   14
  4  ω    -37.00  51.00   2.00  115.00    --  -18.14  57.00 150.00   44
  5  ω     -8.00  48.00   2.00  115.00    --  -18.14  77.00 -90.00   28
  6  ω    -50.00  34.00   2.00  115.00    --   19.23 -57.00  30.00   42
  7  ω    -20.00  60.00   2.00  115.00    --   19.23 -99.00-120.00   40
  8  ω     10.00  60.00   2.00  115.00    --   19.23 -99.00 -30.00   25
  9  ω     -8.00  86.00   2.00  115.00    --   19.23  77.00 -90.00   47
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1513876000
_diffrn_orient_matrix_UB_12      0.0244850000
_diffrn_orient_matrix_UB_13      0.0124228000
_diffrn_orient_matrix_UB_21      -0.0982696000
_diffrn_orient_matrix_UB_22      -0.0160883000
_diffrn_orient_matrix_UB_23      -0.0495076000
_diffrn_orient_matrix_UB_31      -0.0632326000
_diffrn_orient_matrix_UB_32      -0.0336065000
_diffrn_orient_matrix_UB_33      0.0327294000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1030
_reflns_number_total             1216
_reflns_odcompleteness_completeness 99.73
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         5.350
_refine_diff_density_min         -4.497
_refine_diff_density_rms         0.303
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.323
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     79
_refine_ls_number_reflns         1216
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1281
_refine_ls_R_factor_gt           0.1171
_refine_ls_restrained_S_all      1.323
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2838
_refine_ls_wR_factor_ref         0.3002
_refine_special_details          
;
 Refined as a 2-component perfect twin.
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C5(H5), C6(H6)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.5000 0.5000 0.5000 0.0214(7) Uani 1 2 d S T P . .
Cl1 Cl 0.8493(6) 0.55220(13) 0.36365(17) 0.0204(7) Uani 1 1 d . . . . .
F3 F 0.184(2) 0.3025(5) 0.1474(5) 0.051(2) Uani 1 1 d . . . . .
N1 N 0.483(2) 0.3869(5) 0.4186(6) 0.0216(17) Uani 1 1 d . . . . .
C2 C 0.354(3) 0.3812(6) 0.3119(8) 0.025(2) Uani 1 1 d . . . . .
H2 H 0.2738 0.4297 0.2734 0.030 Uiso 1 1 calc R . . . .
C3 C 0.334(3) 0.3052(7) 0.2547(9) 0.029(2) Uani 1 1 d . . . . .
C4 C 0.458(3) 0.2326(6) 0.3094(8) 0.026(2) Uani 1 1 d . . . . .
H4 H 0.4467 0.1810 0.2718 0.031 Uiso 1 1 calc R . . . .
C5 C 0.597(3) 0.2387(6) 0.4193(8) 0.026(2) Uani 1 1 d . . . . .
H5 H 0.6883 0.1915 0.4585 0.031 Uiso 1 1 calc R . . . .
C6 C 0.601(3) 0.3174(6) 0.4727(9) 0.026(2) Uani 1 1 d . . . . .
H6 H 0.6899 0.3214 0.5489 0.031 Uiso 1 1 calc R . . . .


_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 Cl1 2.295(2) . ?
Cu1 Cl1 2.295(2) 3_666 ?
Cu1 N1 2.035(7) . ?
Cu1 N1 2.035(7) 3_666 ?
F3 C3 1.336(12) . ?
N1 C2 1.308(12) . ?
N1 C6 1.333(13) . ?
C2 H2 0.9300 . ?
C2 C3 1.382(14) . ?
C3 C4 1.384(16) . ?
C4 H4 0.9300 . ?
C4 C5 1.355(14) . ?
C5 H5 0.9300 . ?
C5 C6 1.401(14) . ?
C6 H6 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
Cl1 Cu1 Cl1 180.00(9) . 3_666 ?
N1 Cu1 Cl1 90.5(2) . 3_666 ?
N1 Cu1 Cl1 90.5(2) 3_666 . ?
N1 Cu1 Cl1 89.5(2) . . ?
N1 Cu1 Cl1 89.5(2) 3_666 3_666 ?
N1 Cu1 N1 180.0 . 3_666 ?
C2 N1 Cu1 120.4(6) . . ?
C2 N1 C6 118.8(8) . . ?
C6 N1 Cu1 120.8(6) . . ?
N1 C2 H2 119.1 . . ?
N1 C2 C3 121.8(9) . . ?
C3 C2 H2 119.1 . . ?
F3 C3 C2 119.2(10) . . ?
F3 C3 C4 120.6(8) . . ?
C2 C3 C4 120.1(9) . . ?
C3 C4 H4 121.0 . . ?
C5 C4 C3 118.0(8) . . ?
C5 C4 H4 121.0 . . ?
C4 C5 H5 120.6 . . ?
C4 C5 C6 118.7(9) . . ?
C6 C5 H5 120.6 . . ?
N1 C6 C5 122.5(9) . . ?
N1 C6 H6 118.8 . . ?
C5 C6 H6 118.8 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.144
_oxdiff_exptl_absorpt_empirical_full_min 0.809
####################################################################### 
# 
# 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_6_2_CuCl2
_database_code_depnum_ccdc_archive 'CCDC 1821334'
_audit_update_record             
;
2018-02-01 deposited with the CCDC.
2018-03-02 downloaded from the CCDC.
;
_audit_creation_date             2018-01-23
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.07.20 svn.r3457 for OlexSys, GUI svn.r5370)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C10 H6 Br2 Cl4 Cu N2'
_chemical_formula_sum            'C10 H6 Br2 Cl4 Cu N2'
_chemical_formula_weight         519.33
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 '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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
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                   8.1656(16)
_cell_length_b                   12.708(3)
_cell_length_c                   14.591(3)
_cell_angle_alpha                90
_cell_angle_beta                 91.79(3)
_cell_angle_gamma                90
_cell_volume                     1513.4(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1250
_cell_measurement_temperature    170.0(1)
_cell_measurement_theta_max      28.283
_cell_measurement_theta_min      0.407
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    7.414
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.4806
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2012/1 (Bruker,2012) was used for absorption correction. wR2(int) was 0.1122 before and 0.0461 after correction. The Ratio of minimum to maximum transmission is 0.6445. The λ/2 correction factor is 0.0015.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            green
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    2.279
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             988
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.13
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0208
_diffrn_reflns_av_unetI/netI     0.0331
_diffrn_reflns_Laue_measured_fraction_full 0.979
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            2880
_diffrn_reflns_point_group_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        25.241
_diffrn_reflns_theta_max         25.241
_diffrn_reflns_theta_min         2.966
_diffrn_ambient_temperature      170.0(1)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1224
_reflns_number_total             1341
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.332
_refine_diff_density_min         -0.371
_refine_diff_density_rms         0.078
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     87
_refine_ls_number_reflns         1341
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0277
_refine_ls_R_factor_gt           0.0237
_refine_ls_restrained_S_all      1.060
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0072P)²+4.2282P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0526
_refine_ls_wR_factor_ref         0.0543
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br2 Br 0.35668(4) 0.08036(3) 0.34809(2) 0.03286(13) Uani 1 1 d . . . . .
Cu1 Cu 0.5000 0.29458(4) 0.2500 0.02006(14) Uani 1 2 d S T P . .
Cl1 Cl 0.75616(8) 0.35444(6) 0.24197(5) 0.02715(18) Uani 1 1 d . . . . .
Cl5 Cl 0.65997(11) 0.43672(6) 0.60189(5) 0.0346(2) Uani 1 1 d . . . . .
N1 N 0.5151(3) 0.26776(18) 0.38645(15) 0.0201(5) Uani 1 1 d . . . . .
C2 C 0.4451(4) 0.1856(2) 0.42589(19) 0.0231(6) Uani 1 1 d . . . . .
C3 C 0.4361(4) 0.1734(3) 0.5201(2) 0.0282(7) Uani 1 1 d . . . . .
H3 H 0.3863 0.1146 0.5450 0.034 Uiso 1 1 calc R . . . .
C4 C 0.5033(4) 0.2512(3) 0.57593(19) 0.0272(7) Uani 1 1 d . . . . .
H4 H 0.4993 0.2461 0.6394 0.033 Uiso 1 1 calc R . . . .
C5 C 0.5763(3) 0.3362(2) 0.53534(18) 0.0228(6) Uani 1 1 d . . . . .
C6 C 0.5821(4) 0.3428(2) 0.44110(19) 0.0229(6) Uani 1 1 d . . . . .
H6 H 0.6333 0.4002 0.4147 0.027 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br2 C2 1.883(3) . ?
Cu1 Cl1 2.2323(8) . ?
Cu1 Cl1 2.2322(8) 2_655 ?
Cu1 N1 2.020(2) 2_655 ?
Cu1 N1 2.020(2) . ?
Cl5 C5 1.732(3) . ?
N1 C2 1.330(4) . ?
N1 C6 1.348(4) . ?
C2 C3 1.387(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.384(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.377(4) . ?
C5 C6 1.380(4) . ?
C6 H6 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
Cl1 Cu1 Cl1 140.15(5) 2_655 . ?
N1 Cu1 Cl1 91.96(7) 2_655 . ?
N1 Cu1 Cl1 91.97(7) . 2_655 ?
N1 Cu1 Cl1 94.63(7) . . ?
N1 Cu1 Cl1 94.63(7) 2_655 2_655 ?
N1 Cu1 N1 160.57(13) . 2_655 ?
C2 N1 Cu1 123.02(19) . . ?
C2 N1 C6 118.1(2) . . ?
C6 N1 Cu1 118.35(19) . . ?
N1 C2 Br2 117.3(2) . . ?
N1 C2 C3 123.6(3) . . ?
C3 C2 Br2 119.1(2) . . ?
C2 C3 H3 120.9 . . ?
C4 C3 C2 118.1(3) . . ?
C4 C3 H3 120.9 . . ?
C3 C4 H4 120.8 . . ?
C5 C4 C3 118.5(3) . . ?
C5 C4 H4 120.8 . . ?
C4 C5 Cl5 120.4(2) . . ?
C4 C5 C6 120.3(3) . . ?
C6 C5 Cl5 119.2(2) . . ?
N1 C6 C5 121.4(3) . . ?
N1 C6 H6 119.3 . . ?
C5 C6 H6 119.3 . . ?

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
Br2 C2 C3 C4 179.4(2) . . . . ?
Cu1 N1 C2 Br2 9.6(3) . . . . ?
Cu1 N1 C2 C3 -171.3(2) . . . . ?
Cu1 N1 C6 C5 171.1(2) . . . . ?
Cl5 C5 C6 N1 -178.4(2) . . . . ?
N1 C2 C3 C4 0.2(5) . . . . ?
C2 N1 C6 C5 -1.1(4) . . . . ?
C2 C3 C4 C5 -0.3(5) . . . . ?
C3 C4 C5 Cl5 179.1(2) . . . . ?
C3 C4 C5 C6 -0.2(4) . . . . ?
C4 C5 C6 N1 1.0(4) . . . . ?
C6 N1 C2 Br2 -178.6(2) . . . . ?
C6 N1 C2 C3 0.5(4) . . . . ?

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

data_8_2_CuCl2
_database_code_depnum_ccdc_archive 'CCDC 1821336'
_audit_update_record             
;
2018-02-01 deposited with the CCDC.
2018-03-02 downloaded from the CCDC.
;
_audit_creation_date             2018-01-23
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.07.20 svn.r3457 for OlexSys, GUI svn.r5370)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C10 H6 Br2 Cl2 Cu I2 N2'
_chemical_formula_sum            'C10 H6 Br2 Cl2 Cu I2 N2'
_chemical_formula_weight         702.23
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 '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'
I I -0.4742 1.8119 '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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
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                   8.4827(17)
_cell_length_b                   13.075(3)
_cell_length_c                   14.721(3)
_cell_angle_alpha                90
_cell_angle_beta                 90.35(3)
_cell_angle_gamma                90
_cell_volume                     1632.7(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2477
_cell_measurement_temperature    170.0(1)
_cell_measurement_theta_max      27.878
_cell_measurement_theta_min      0.407
_shelx_estimated_absorpt_T_max   0.396
_shelx_estimated_absorpt_T_min   0.273
_exptl_absorpt_coefficient_mu    10.328
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.4729
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2012/1 (Bruker,2012) was used for absorption correction. wR2(int) was 0.1084 before and 0.0526 after correction. The Ratio of minimum to maximum transmission is 0.6342. The λ/2 correction factor is 0.0015.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            green
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    2.857
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1276
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0350
_diffrn_reflns_av_unetI/netI     0.0344
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            8216
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.333
_diffrn_reflns_theta_min         2.767
_diffrn_ambient_temperature      170.0(1)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1755
_reflns_number_total             2027
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.593
_refine_diff_density_min         -0.658
_refine_diff_density_rms         0.133
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     87
_refine_ls_number_reflns         2027
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0316
_refine_ls_R_factor_gt           0.0243
_refine_ls_restrained_S_all      1.051
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0142P)²+3.8871P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0495
_refine_ls_wR_factor_ref         0.0514
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I5 I 0.34884(3) 0.44146(2) 0.61371(2) 0.02453(8) Uani 1 1 d . . . . .
Br2 Br 0.64587(5) 0.07715(3) 0.34696(2) 0.03085(10) Uani 1 1 d . . . . .
Cu1 Cu 0.5000 0.28564(4) 0.2500 0.01808(13) Uani 1 2 d S T P . .
Cl1 Cl 0.74556(9) 0.34996(7) 0.25902(5) 0.02370(18) Uani 1 1 d . . . . .
N1 N 0.4901(3) 0.2582(2) 0.38474(16) 0.0182(6) Uani 1 1 d . . . . .
C2 C 0.5583(4) 0.1778(3) 0.4238(2) 0.0218(7) Uani 1 1 d . . . . .
C3 C 0.5655(4) 0.1629(3) 0.5171(2) 0.0293(8) Uani 1 1 d . . . . .
H3 H 0.6130 0.1033 0.5421 0.035 Uiso 1 1 calc R . . . .
C4 C 0.5015(4) 0.2372(3) 0.5727(2) 0.0262(8) Uani 1 1 d . . . . .
H4 H 0.5046 0.2301 0.6369 0.031 Uiso 1 1 calc R . . . .
C5 C 0.4332(4) 0.3219(3) 0.5328(2) 0.0194(7) Uani 1 1 d . . . . .
C6 C 0.4260(4) 0.3300(3) 0.43931(19) 0.0192(7) Uani 1 1 d . . . . .
H6 H 0.3747 0.3873 0.4127 0.023 Uiso 1 1 calc R . . . .


_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
I5 C5 2.094(3) . ?
Br2 C2 1.891(3) . ?
Cu1 Cl1 2.2496(9) . ?
Cu1 Cl1 2.2496(9) 2_655 ?
Cu1 N1 2.018(2) . ?
Cu1 N1 2.018(2) 2_655 ?
N1 C2 1.329(4) . ?
N1 C6 1.352(4) . ?
C2 C3 1.388(4) . ?
C3 H3 0.9500 . ?
C3 C4 1.383(5) . ?
C4 H4 0.9500 . ?
C4 C5 1.379(5) . ?
C5 C6 1.381(4) . ?
C6 H6 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
Cl1 Cu1 Cl1 136.09(6) 2_655 . ?
N1 Cu1 Cl1 94.62(8) 2_655 . ?
N1 Cu1 Cl1 94.62(8) . 2_655 ?
N1 Cu1 Cl1 93.00(8) . . ?
N1 Cu1 Cl1 93.00(8) 2_655 2_655 ?
N1 Cu1 N1 159.54(16) . 2_655 ?
C2 N1 Cu1 123.1(2) . . ?
C2 N1 C6 117.9(3) . . ?
C6 N1 Cu1 118.7(2) . . ?
N1 C2 Br2 117.6(2) . . ?
N1 C2 C3 123.8(3) . . ?
C3 C2 Br2 118.6(3) . . ?
C2 C3 H3 121.0 . . ?
C4 C3 C2 118.1(3) . . ?
C4 C3 H3 121.0 . . ?
C3 C4 H4 120.7 . . ?
C5 C4 C3 118.5(3) . . ?
C5 C4 H4 120.7 . . ?
C4 C5 I5 120.1(2) . . ?
C4 C5 C6 120.1(3) . . ?
C6 C5 I5 119.7(2) . . ?
N1 C6 C5 121.6(3) . . ?
N1 C6 H6 119.2 . . ?
C5 C6 H6 119.2 . . ?

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

data_3_4_CuCl2_2
_database_code_depnum_ccdc_archive 'CCDC 1821329'
_audit_update_record             
;
2018-02-01 deposited with the CCDC.
2018-03-02 downloaded from the CCDC.
;
_audit_creation_date             2018-01-23
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.07.20 svn.r3457 for OlexSys, GUI svn.r5370)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H12 Br4 Cl8 Cu2 N4'
_chemical_formula_sum            'C20 H12 Br4 Cl8 Cu2 N4'
_chemical_formula_weight         1038.66
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 '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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           12
_space_group_name_H-M_alt        'I 1 2/m 1'
_space_group_name_Hall           '-I 2y'
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'
'-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                   7.8894(16)
_cell_length_b                   14.316(3)
_cell_length_c                   13.494(3)
_cell_angle_alpha                90
_cell_angle_beta                 92.06(3)
_cell_angle_gamma                90
_cell_volume                     1523.1(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1785
_cell_measurement_temperature    170.0(1)
_cell_measurement_theta_max      27.878
_cell_measurement_theta_min      0.407
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    7.367
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.5248
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2012/1 (Bruker,2012) was used for absorption correction. wR2(int) was 0.0944 before and 0.0549 after correction. The Ratio of minimum to maximum transmission is 0.7038. The λ/2 correction factor is 0.0015.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            green
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    2.265
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             988
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.14
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0279
_diffrn_reflns_av_unetI/netI     0.0325
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            4917
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.237
_diffrn_reflns_theta_max         25.237
_diffrn_reflns_theta_min         2.846
_diffrn_ambient_temperature      170.0(1)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1299
_reflns_number_total             1448
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.362
_refine_diff_density_min         -0.376
_refine_diff_density_rms         0.081
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     91
_refine_ls_number_reflns         1448
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0259
_refine_ls_R_factor_gt           0.0212
_refine_ls_restrained_S_all      1.051
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0054P)²+3.1348P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0450
_refine_ls_wR_factor_ref         0.0466
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br5 Br 0.71848(4) 0.86088(2) 0.64719(2) 0.02651(10) Uani 1 1 d . . . . .
Cu1 Cu 0.39487(6) 0.5000 0.61713(3) 0.01446(12) Uani 1 2 d S T P . .
Cl1 Cl 0.44355(12) 0.5000 0.78395(6) 0.0196(2) Uani 1 2 d S T P . .
Cl1' Cl 0.29834(11) 0.5000 0.45236(6) 0.01552(19) Uani 1 2 d S T P . .
Cl2 Cl 0.05098(9) 0.61928(5) 0.62383(5) 0.02407(16) Uani 1 1 d . . . . .
N1 N 0.3793(3) 0.64283(14) 0.62127(14) 0.0160(5) Uani 1 1 d . . . . .
C2 C 0.2298(3) 0.68718(18) 0.62219(18) 0.0177(6) Uani 1 1 d . . . . .
C3 C 0.2150(4) 0.78328(19) 0.62453(19) 0.0236(6) Uani 1 1 d . . . . .
H3 H 0.1088 0.8115 0.6226 0.028 Uiso 1 1 calc R . . . .
C4 C 0.3605(4) 0.83641(19) 0.62976(19) 0.0228(6) Uani 1 1 d . . . . .
H4 H 0.3547 0.9013 0.6316 0.027 Uiso 1 1 calc R . . . .
C5 C 0.5155(3) 0.79127(18) 0.63220(18) 0.0189(6) Uani 1 1 d . . . . .
C6 C 0.5218(3) 0.69516(18) 0.62734(17) 0.0179(6) Uani 1 1 d . . . . .
H6 H 0.6268 0.6656 0.6283 0.021 Uiso 1 1 calc R . . . .


_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
Br5 C5 1.891(3) . ?
Cu1 Cl1 2.2699(11) . ?
Cu1 Cl1' 2.6270(12) 5_666 ?
Cu1 Cl1' 2.3241(11) . ?
Cu1 N1 2.049(2) 6_565 ?
Cu1 N1 2.049(2) . ?
Cl1' Cu1 2.6270(11) 5_666 ?
Cl2 C2 1.714(3) . ?
N1 C2 1.339(3) . ?
N1 C6 1.351(3) . ?
C2 C3 1.381(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.377(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.382(4) . ?
C5 C6 1.378(4) . ?
C6 H6 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
Cl1 Cu1 Cl1' 103.23(4) . 5_666 ?
Cl1 Cu1 Cl1' 170.62(4) . . ?
Cl1' Cu1 Cl1' 86.15(4) . 5_666 ?
N1 Cu1 Cl1 88.92(5) 6_565 . ?
N1 Cu1 Cl1 88.92(5) . . ?
N1 Cu1 Cl1' 93.83(6) 6_565 5_666 ?
N1 Cu1 Cl1' 90.47(6) 6_565 . ?
N1 Cu1 Cl1' 90.47(6) . . ?
N1 Cu1 Cl1' 93.83(6) . 5_666 ?
N1 Cu1 N1 172.33(12) 6_565 . ?
Cu1 Cl1' Cu1 93.85(4) . 5_666 ?
C2 N1 Cu1 121.81(17) . . ?
C2 N1 C6 117.9(2) . . ?
C6 N1 Cu1 120.28(17) . . ?
N1 C2 Cl2 117.2(2) . . ?
N1 C2 C3 123.2(3) . . ?
C3 C2 Cl2 119.6(2) . . ?
C2 C3 H3 120.7 . . ?
C4 C3 C2 118.7(3) . . ?
C4 C3 H3 120.7 . . ?
C3 C4 H4 120.7 . . ?
C3 C4 C5 118.6(3) . . ?
C5 C4 H4 120.7 . . ?
C4 C5 Br5 120.1(2) . . ?
C6 C5 Br5 120.0(2) . . ?
C6 C5 C4 119.9(3) . . ?
N1 C6 C5 121.7(3) . . ?
N1 C6 H6 119.2 . . ?
C5 C6 H6 119.2 . . ?

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

data_3IPy_2_CuCl2
_database_code_depnum_ccdc_archive 'CCDC 1821338'
_audit_update_record             
;
2018-02-01 deposited with the CCDC.
2018-03-02 downloaded from the CCDC.
;
_audit_creation_date             2018-01-12
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C10 H8 Cl2 Cu I2 N2'
_chemical_formula_sum            'C10 H8 Cl2 Cu I2 N2'
_chemical_formula_weight         544.42
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C20 H20 N2 Cu1 I1 Cl1'
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'
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'
I I -0.4742 1.8119 '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'

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

_cell_length_a                   4.0102(7)
_cell_length_b                   8.4892(13)
_cell_length_c                   10.1403(13)
_cell_angle_alpha                90.863(12)
_cell_angle_beta                 92.738(13)
_cell_angle_gamma                97.811(14)
_cell_volume                     341.54(9)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    1262
_cell_measurement_temperature    120.0(1)
_cell_measurement_theta_max      28.7230
_cell_measurement_theta_min      4.0340
_exptl_absorpt_coefficient_mu    6.487
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82026
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            green
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    2.647
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             251
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 -2 14 0.0073
0 2 -14 0.0104
-6 1 3 0.0466
6 -1 -1 0.0752
-1 -9 -8 0.0073
0 10 6 0.0171
2 -10 7 0.0209
0 -11 -5 0.0084
1 11 1 0.0164

_exptl_crystal_size_max          0.125
_exptl_crystal_size_mid          0.027
_exptl_crystal_size_min          0.026
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-1.0000 -2.0000 14.0000 -0.2450 -0.4435 -0.8653
-0.0000 2.0000 -14.0000 0.1457 0.3099 0.9304
-6.0000 1.0000 3.0000 -0.5189 -0.9175 0.2098
6.0000 -1.0000 -1.0000 0.5197 0.8633 -0.3390
-1.0000 -9.0000 -8.0000 -0.7852 0.3944 0.4647
0.0000 10.0000 6.0000 0.7608 -0.5084 -0.2574
2.0000 -10.0000 7.0000 -0.5566 0.4236 -0.7125
-0.0000 -11.0000 -5.0000 -0.8362 0.5159 0.1798
1.0000 11.0000 1.0000 0.9339 -0.2740 0.0135

_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0246
_diffrn_reflns_av_unetI/netI     0.0406
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            2007
_diffrn_reflns_theta_full        25.24
_diffrn_reflns_theta_max         25.24
_diffrn_reflns_theta_min         3.12
_diffrn_ambient_temperature      120.0(1)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0107
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -2.00  88.00   2.00  110.00    --   19.23  57.00-120.00   45
  2  ω     23.00  75.00   2.00  110.00    --   19.23  57.00  30.00   26
  3  ω    -11.00  89.00   2.00  110.00    --   19.23  77.00 120.00   50
  4  ω    -17.00  57.00   2.00  110.00    --   19.23 -99.00 -30.00   37
  5  ω    -50.00 -22.00   2.00  110.00    --   19.23 -57.00  90.00   14
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0993294000
_diffrn_orient_matrix_UB_12      0.0758271000
_diffrn_orient_matrix_UB_13      0.0004288000
_diffrn_orient_matrix_UB_21      0.1336041000
_diffrn_orient_matrix_UB_22      -0.0345945000
_diffrn_orient_matrix_UB_23      -0.0270795000
_diffrn_orient_matrix_UB_31      -0.0650933000
_diffrn_orient_matrix_UB_32      0.0130139000
_diffrn_orient_matrix_UB_33      -0.0645976000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_number_gt                1126
_reflns_number_total             1231
_reflns_odcompleteness_completeness 99.57
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         1.162
_refine_diff_density_min         -0.607
_refine_diff_density_rms         0.153
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     79
_refine_ls_number_reflns         1231
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0307
_refine_ls_R_factor_gt           0.0263
_refine_ls_restrained_S_all      1.092
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0248P)²+0.1208P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0582
_refine_ls_wR_factor_ref         0.0608
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C5(H5), C6(H6)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_site_symmetry_order
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
I3 I 0.80917(8) 0.71589(4) -0.04202(3) 0.01736(13) Uani 1 d . . 1 . . .
Cu1 Cu 0.5000 0.5000 0.5000 0.0244(2) Uani 1 d . . 2 S T P
Cl1 Cl 0.9125(3) 0.65092(15) 0.63044(12) 0.0190(3) Uani 1 d . . 1 . . .
N1 N 0.5296(10) 0.6706(5) 0.3640(4) 0.0195(10) Uani 1 d . . 1 . . .
C2 C 0.6383(12) 0.6457(6) 0.2431(5) 0.0185(11) Uani 1 d . . 1 . . .
H2 H 0.6994 0.5470 0.2217 0.022 Uiso 1 calc . . 1 R . .
C3 C 0.6620(12) 0.7639(6) 0.1489(5) 0.0156(11) Uani 1 d . . 1 . . .
C4 C 0.5721(12) 0.9104(6) 0.1799(5) 0.0181(11) Uani 1 d . . 1 . . .
H4 H 0.5915 0.9912 0.1186 0.022 Uiso 1 calc . . 1 R . .
C5 C 0.4533(12) 0.9363(6) 0.3026(5) 0.0195(11) Uani 1 d . . 1 . . .
H5 H 0.3858 1.0334 0.3249 0.023 Uiso 1 calc . . 1 R . .
C6 C 0.4372(13) 0.8124(7) 0.3925(5) 0.0223(12) Uani 1 d . . 1 . . .
H6 H 0.3588 0.8293 0.4757 0.027 Uiso 1 calc . . 1 R . .


_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
I3 C3 2.101(5) . ?
Cu1 Cl1 2.3002(13) . ?
Cu1 Cl1 2.3002(13) 2_666 ?
Cu1 N1 2.010(4) 2_666 ?
Cu1 N1 2.010(4) . ?
N1 C2 1.344(6) . ?
N1 C6 1.338(7) . ?
C2 H2 0.9300 . ?
C2 C3 1.392(7) . ?
C3 C4 1.377(7) . ?
C4 H4 0.9300 . ?
C4 C5 1.378(7) . ?
C5 H5 0.9300 . ?
C5 C6 1.400(7) . ?
C6 H6 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
Cl1 Cu1 Cl1 180.0 2_666 . ?
N1 Cu1 Cl1 90.24(12) . . ?
N1 Cu1 Cl1 90.24(12) 2_666 2_666 ?
N1 Cu1 Cl1 89.76(12) 2_666 . ?
N1 Cu1 Cl1 89.76(12) . 2_666 ?
N1 Cu1 N1 179.999(1) 2_666 . ?
C2 N1 Cu1 121.5(4) . . ?
C6 N1 Cu1 120.0(4) . . ?
C6 N1 C2 118.4(4) . . ?
N1 C2 H2 119.1 . . ?
N1 C2 C3 121.8(5) . . ?
C3 C2 H2 119.1 . . ?
C2 C3 I3 120.4(4) . . ?
C4 C3 I3 120.1(4) . . ?
C4 C3 C2 119.4(5) . . ?
C3 C4 H4 120.3 . . ?
C3 C4 C5 119.4(5) . . ?
C5 C4 H4 120.3 . . ?
C4 C5 H5 120.9 . . ?
C4 C5 C6 118.1(5) . . ?
C6 C5 H5 120.9 . . ?
N1 C6 C5 122.9(5) . . ?
N1 C6 H6 118.6 . . ?
C5 C6 H6 118.6 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.110
_oxdiff_exptl_absorpt_empirical_full_min 0.891
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_5_2_2_CuCl2
_database_code_depnum_ccdc_archive 'CCDC 1821333'
_audit_update_record             
;
2018-02-01 deposited with the CCDC.
2018-03-02 downloaded from the CCDC.
;
_audit_creation_date             2018-01-23
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.07.20 svn.r3457 for OlexSys, GUI svn.r5370)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C10 H6 Br2 Cl2 Cu F2 N2'
_chemical_formula_sum            'C10 H6 Br2 Cl2 Cu F2 N2'
_chemical_formula_weight         486.43
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 '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'
F F 0.0171 0.0103 '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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   5.7104(11)
_cell_length_b                   11.981(2)
_cell_length_c                   10.478(2)
_cell_angle_alpha                90
_cell_angle_beta                 103.66(3)
_cell_angle_gamma                90
_cell_volume                     696.6(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1804
_cell_measurement_temperature    170.0(1)
_cell_measurement_theta_max      27.878
_cell_measurement_theta_min      0.407
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    7.694
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.5931
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2012/1 (Bruker,2012) was used for absorption correction. wR2(int) was 0.0711 before and 0.0497 after correction. The Ratio of minimum to maximum transmission is 0.7954. The λ/2 correction factor is 0.0015.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.319
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             462
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.09
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0366
_diffrn_reflns_av_unetI/netI     0.0305
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            5238
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.222
_diffrn_reflns_theta_max         25.222
_diffrn_reflns_theta_min         2.625
_diffrn_ambient_temperature      170.0(1)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1112
_reflns_number_total             1260
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.299
_refine_diff_density_min         -0.322
_refine_diff_density_rms         0.075
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     88
_refine_ls_number_reflns         1260
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0261
_refine_ls_R_factor_gt           0.0206
_refine_ls_restrained_S_all      1.042
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0204P)²+0.3777P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0471
_refine_ls_wR_factor_ref         0.0488
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br2 Br 0.28540(5) 0.34822(2) 0.68718(3) 0.02918(11) Uani 1 1 d . . . . .
Cu1 Cu 0.5000 0.5000 0.5000 0.01904(13) Uani 1 2 d S T P . .
Cl1 Cl 0.80930(13) 0.54612(6) 0.66827(6) 0.02552(17) Uani 1 1 d . . . . .
F5 F 0.9850(3) 0.14090(13) 0.42505(18) 0.0403(5) Uani 1 1 d . . . . .
N1 N 0.5964(4) 0.33902(17) 0.5247(2) 0.0187(5) Uani 1 1 d . . . . .
C2 C 0.5010(5) 0.2750(2) 0.6031(2) 0.0219(6) Uani 1 1 d . . . . .
C3 C 0.5514(6) 0.1635(2) 0.6233(3) 0.0265(6) Uani 1 1 d . . . . .
H3 H 0.4767 0.1214 0.6769 0.032 Uiso 1 1 calc R . . . .
C4 C 0.7157(5) 0.1152(2) 0.5623(3) 0.0278(6) Uani 1 1 d . . . . .
H4 H 0.7554 0.0400 0.5735 0.033 Uiso 1 1 calc R . . . .
C5 C 0.8185(5) 0.1827(2) 0.4843(3) 0.0265(6) Uani 1 1 d . . . . .
C6 C 0.7567(5) 0.2933(2) 0.4651(2) 0.0224(6) Uani 1 1 d . . . . .
H6 H 0.8264 0.3367 0.4104 0.027 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br2 C2 1.890(2) . ?
Cu1 Cl1 2.2500(10) . ?
Cu1 Cl1 2.2500(10) 3_666 ?
Cu1 N1 2.006(2) . ?
Cu1 N1 2.006(2) 3_666 ?
F5 C5 1.348(3) . ?
N1 C2 1.331(3) . ?
N1 C6 1.341(3) . ?
C2 C3 1.372(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.381(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.377(4) . ?
C5 C6 1.374(4) . ?
C6 H6 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
Cl1 Cu1 Cl1 180.0 . 3_666 ?
N1 Cu1 Cl1 90.33(7) . 3_666 ?
N1 Cu1 Cl1 90.33(7) 3_666 . ?
N1 Cu1 Cl1 89.67(7) . . ?
N1 Cu1 Cl1 89.67(7) 3_666 3_666 ?
N1 Cu1 N1 180.00(13) . 3_666 ?
C2 N1 Cu1 119.60(17) . . ?
C2 N1 C6 118.4(2) . . ?
C6 N1 Cu1 121.96(17) . . ?
N1 C2 Br2 115.25(19) . . ?
N1 C2 C3 123.7(2) . . ?
C3 C2 Br2 121.06(19) . . ?
C2 C3 H3 120.8 . . ?
C2 C3 C4 118.5(2) . . ?
C4 C3 H3 120.8 . . ?
C3 C4 H4 121.3 . . ?
C5 C4 C3 117.4(3) . . ?
C5 C4 H4 121.3 . . ?
F5 C5 C4 120.0(3) . . ?
F5 C5 C6 118.4(2) . . ?
C6 C5 C4 121.6(2) . . ?
N1 C6 C5 120.4(2) . . ?
N1 C6 H6 119.8 . . ?
C5 C6 H6 119.8 . . ?

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

data_5_1_4_CuCl2_2
_database_code_depnum_ccdc_archive 'CCDC 1821332'
_audit_update_record             
;
2018-02-01 deposited with the CCDC.
2018-03-02 downloaded from the CCDC.
;
_audit_creation_date             2018-01-23
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.07.20 svn.r3457 for OlexSys, GUI svn.r5370)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H12 Br4 Cl4 Cu2 F4 N4'
_chemical_formula_sum            'C20 H12 Br4 Cl4 Cu2 F4 N4'
_chemical_formula_weight         972.86
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 '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'
F F 0.0171 0.0103 '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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           12
_space_group_name_H-M_alt        'C 1 2/m 1'
_space_group_name_Hall           '-C 2y'
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'
'-x, -y, -z'
'x, -y, z'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z'

_cell_length_a                   14.946(3)
_cell_length_b                   15.233(3)
_cell_length_c                   6.7384(13)
_cell_angle_alpha                90
_cell_angle_beta                 91.82(3)
_cell_angle_gamma                90
_cell_volume                     1533.4(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1702
_cell_measurement_temperature    170.0(1)
_cell_measurement_theta_max      27.485
_cell_measurement_theta_min      0.407
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    6.990
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_correction_T_min  0.4994
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2012/1 (Bruker,2012) was used for absorption correction. wR2(int) was 0.1413 before and 0.0512 after correction. The Ratio of minimum to maximum transmission is 0.6696. The λ/2 correction factor is 0.0015.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            green
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    2.107
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             924
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0270
_diffrn_reflns_av_unetI/netI     0.0288
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            4678
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.245
_diffrn_reflns_theta_max         25.245
_diffrn_reflns_theta_min         2.674
_diffrn_ambient_temperature      170.0(1)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1320
_reflns_number_total             1436
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.275
_refine_diff_density_min         -0.372
_refine_diff_density_rms         0.069
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     91
_refine_ls_number_reflns         1436
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0226
_refine_ls_R_factor_gt           0.0197
_refine_ls_restrained_S_all      1.079
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0137P)²+2.2744P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0473
_refine_ls_wR_factor_ref         0.0483
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br2 Br 0.29868(2) 0.37915(2) 0.88240(3) 0.02943(10) Uani 1 1 d . . . . .
Cu1 Cu 0.37886(3) 0.5000 0.50691(5) 0.01787(11) Uani 1 2 d S T P . .
Cl1 Cl 0.25497(6) 0.5000 0.30317(12) 0.02451(19) Uani 1 2 d S T P . .
Cl1' Cl 0.48920(5) 0.5000 0.74824(10) 0.02041(18) Uani 1 2 d S T P . .
F5 F 0.43121(11) 0.19148(10) 0.1827(2) 0.0396(4) Uani 1 1 d . . . . .
N1 N 0.37375(13) 0.36453(13) 0.5143(3) 0.0202(4) Uani 1 1 d . . . . .
C2 C 0.34354(16) 0.31687(15) 0.6648(3) 0.0226(5) Uani 1 1 d . . . . .
C3 C 0.34271(17) 0.22593(16) 0.6666(4) 0.0280(6) Uani 1 1 d . . . . .
H3 H 0.3222 0.1955 0.7758 0.034 Uiso 1 1 calc R . . . .
C4 C 0.37279(17) 0.18126(16) 0.5040(4) 0.0301(6) Uani 1 1 d . . . . .
H4 H 0.3735 0.1202 0.4999 0.036 Uiso 1 1 calc R . . . .
C5 C 0.40148(17) 0.23060(16) 0.3492(4) 0.0263(6) Uani 1 1 d . . . . .
C6 C 0.40220(16) 0.32074(16) 0.3549(3) 0.0229(5) Uani 1 1 d . . . . .
H6 H 0.4227 0.3520 0.2468 0.027 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br2 C2 1.887(2) . ?
Cu1 Cl1 2.2697(11) . ?
Cu1 Cl1' 2.6573(11) 5_666 ?
Cu1 Cl1' 2.2788(11) . ?
Cu1 N1 2.0657(19) 6_565 ?
Cu1 N1 2.066(2) . ?
Cl1' Cu1 2.6572(11) 5_666 ?
F5 C5 1.358(3) . ?
N1 C2 1.337(3) . ?
N1 C6 1.345(3) . ?
C2 C3 1.385(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.377(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.366(4) . ?
C5 C6 1.374(3) . ?
C6 H6 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
Cl1 Cu1 Cl1' 102.51(3) . 5_666 ?
Cl1 Cu1 Cl1' 171.70(3) . . ?
Cl1' Cu1 Cl1' 85.79(3) . 5_666 ?
N1 Cu1 Cl1 89.11(6) . . ?
N1 Cu1 Cl1 89.11(6) 6_565 . ?
N1 Cu1 Cl1' 92.54(6) 6_565 5_666 ?
N1 Cu1 Cl1' 92.54(6) . 5_666 ?
N1 Cu1 Cl1' 90.53(5) . . ?
N1 Cu1 Cl1' 90.53(5) 6_565 . ?
N1 Cu1 N1 174.87(11) 6_565 . ?
Cu1 Cl1' Cu1 94.21(3) . 5_666 ?
C2 N1 Cu1 125.04(16) . . ?
C2 N1 C6 117.4(2) . . ?
C6 N1 Cu1 117.60(15) . . ?
N1 C2 Br2 116.95(17) . . ?
N1 C2 C3 123.6(2) . . ?
C3 C2 Br2 119.50(18) . . ?
C2 C3 H3 120.5 . . ?
C4 C3 C2 118.9(2) . . ?
C4 C3 H3 120.5 . . ?
C3 C4 H4 121.5 . . ?
C5 C4 C3 117.0(2) . . ?
C5 C4 H4 121.5 . . ?
F5 C5 C4 120.6(2) . . ?
F5 C5 C6 117.3(2) . . ?
C4 C5 C6 122.1(2) . . ?
N1 C6 C5 121.0(2) . . ?
N1 C6 H6 119.5 . . ?
C5 C6 H6 119.5 . . ?

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
Br2 C2 C3 C4 177.80(19) . . . . ?
Cu1 N1 C2 Br2 2.2(3) . . . . ?
Cu1 N1 C2 C3 -178.66(19) . . . . ?
Cu1 N1 C6 C5 179.53(19) . . . . ?
F5 C5 C6 N1 179.9(2) . . . . ?
N1 C2 C3 C4 -1.3(4) . . . . ?
C2 N1 C6 C5 -1.1(3) . . . . ?
C2 C3 C4 C5 -0.3(4) . . . . ?
C3 C4 C5 F5 -179.3(2) . . . . ?
C3 C4 C5 C6 1.2(4) . . . . ?
C4 C5 C6 N1 -0.5(4) . . . . ?
C6 N1 C2 Br2 -177.16(17) . . . . ?
C6 N1 C2 C3 2.0(4) . . . . ?


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

data_4_2_2_CuCl2
_database_code_depnum_ccdc_archive 'CCDC 1821331'
_audit_update_record             
;
2018-02-01 deposited with the CCDC.
2018-03-02 downloaded from the CCDC.
;
_audit_creation_date             2018-01-18
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelxl_version_number           2013-2
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C10 H6 Cl4 Cu I2 N2'
_chemical_formula_sum            'C10 H6 Cl4 Cu I2 N2'
_chemical_formula_weight         613.31
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'
I I -0.4742 1.8119 '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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
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                   8.3678(17)
_cell_length_b                   13.106(3)
_cell_length_c                   14.700(3)
_cell_angle_alpha                90
_cell_angle_beta                 90.12(3)
_cell_angle_gamma                90
_cell_volume                     1612.1(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2751
_cell_measurement_temperature    170.0(1)
_cell_measurement_theta_max      28.283
_cell_measurement_theta_min      0.407
_shelx_estimated_absorpt_T_max   0.622
_shelx_estimated_absorpt_T_min   0.496
_exptl_absorpt_coefficient_mu    5.834
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.5645
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2012/1 (Bruker,2012) was used for absorption correction. wR2(int) was 0.0759 before and 0.0571 after correction. The Ratio of minimum to maximum transmission is 0.7570. The λ/2 correction factor is 0.0015.'
_exptl_crystal_colour            green
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    2.527
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1132
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.09
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0412
_diffrn_reflns_av_unetI/netI     0.0391
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            9133
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.361
_diffrn_reflns_theta_min         2.771
_diffrn_ambient_temperature      170.0(1)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1629
_reflns_number_total             2009
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.455
_refine_diff_density_min         -0.495
_refine_diff_density_rms         0.126
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     87
_refine_ls_number_reflns         2009
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0434
_refine_ls_R_factor_gt           0.0291
_refine_ls_restrained_S_all      1.020
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0113P)²+4.7682P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0503
_refine_ls_wR_factor_ref         0.0537
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C6(H6), C4(H4), C3(H3)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I5 I 0.64950(3) 0.43731(2) 0.61846(2) 0.03209(9) Uani 1 1 d . . . . .
Cu1 Cu 0.5000 0.29105(5) 0.2500 0.02537(15) Uani 1 2 d S T P . .
Cl1 Cl 0.74852(10) 0.35391(8) 0.24338(6) 0.0323(2) Uani 1 1 d . . . . .
Cl2 Cl 0.36174(13) 0.09056(8) 0.34655(7) 0.0443(3) Uani 1 1 d . . . . .
N1 N 0.5085(3) 0.2609(2) 0.38426(18) 0.0244(6) Uani 1 1 d . . . . .
C5 C 0.5647(4) 0.3205(3) 0.5346(2) 0.0245(7) Uani 1 1 d . . . . .
C6 C 0.5721(4) 0.3306(3) 0.4411(2) 0.0248(7) Uani 1 1 d . . . . .
H6 H 0.6238 0.3887 0.4161 0.030 Uiso 1 1 calc R . . . .
C2 C 0.4400(4) 0.1791(3) 0.4210(2) 0.0278(8) Uani 1 1 d . . . . .
C4 C 0.4947(4) 0.2349(3) 0.5714(2) 0.0339(9) Uani 1 1 d . . . . .
H4 H 0.4895 0.2262 0.6354 0.041 Uiso 1 1 calc R . . . .
C3 C 0.4321(5) 0.1618(3) 0.5138(2) 0.0362(9) Uani 1 1 d . . . . .
H3 H 0.3850 0.1013 0.5373 0.043 Uiso 1 1 calc R . . . .


_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
I5 C5 2.089(3) . ?
Cu1 Cl1 2.2391(10) . ?
Cu1 Cl1 2.2391(10) 2_655 ?
Cu1 N1 2.014(3) . ?
Cu1 N1 2.014(3) 2_655 ?
Cl2 C2 1.724(4) . ?
N1 C6 1.347(4) . ?
N1 C2 1.331(4) . ?
C5 C6 1.382(4) . ?
C5 C4 1.377(5) . ?
C6 H6 0.9500 . ?
C2 C3 1.385(5) . ?
C4 H4 0.9500 . ?
C4 C3 1.380(5) . ?
C3 H3 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
Cl1 Cu1 Cl1 136.82(6) . 2_655 ?
N1 Cu1 Cl1 94.82(9) . . ?
N1 Cu1 Cl1 93.46(9) . 2_655 ?
N1 Cu1 Cl1 94.82(9) 2_655 2_655 ?
N1 Cu1 Cl1 93.46(9) 2_655 . ?
N1 Cu1 N1 157.38(17) . 2_655 ?
C6 N1 Cu1 119.2(2) . . ?
C2 N1 Cu1 122.8(2) . . ?
C2 N1 C6 117.7(3) . . ?
C6 C5 I5 120.0(3) . . ?
C4 C5 I5 120.7(2) . . ?
C4 C5 C6 119.2(3) . . ?
N1 C6 C5 122.2(3) . . ?
N1 C6 H6 118.9 . . ?
C5 C6 H6 118.9 . . ?
N1 C2 Cl2 116.6(3) . . ?
N1 C2 C3 123.6(3) . . ?
C3 C2 Cl2 119.8(3) . . ?
C5 C4 H4 120.5 . . ?
C5 C4 C3 119.1(3) . . ?
C3 C4 H4 120.5 . . ?
C2 C3 H3 120.9 . . ?
C4 C3 C2 118.1(3) . . ?
C4 C3 H3 120.9 . . ?

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

data_4_1_4_CuCl2_2
_database_code_depnum_ccdc_archive 'CCDC 1821330'
_audit_update_record             
;
2018-02-01 deposited with the CCDC.
2018-03-02 downloaded from the CCDC.
;
_audit_creation_date             2018-01-18
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelxl_version_number           2013-2
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C20 H12 Cl8 Cu2 I4 N4'
_chemical_formula_sum            'C20 H12 Cl8 Cu2 I4 N4'
_chemical_formula_weight         1226.62
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'
I I -0.4742 1.8119 '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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           12
_space_group_name_H-M_alt        'I 1 2/m 1'
_space_group_name_Hall           '-I 2y'
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'
'-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                   8.0829(16)
_cell_length_b                   14.605(3)
_cell_length_c                   13.664(3)
_cell_angle_alpha                90
_cell_angle_beta                 91.89(3)
_cell_angle_gamma                90
_cell_volume                     1612.1(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2845
_cell_measurement_temperature    170.0(1)
_cell_measurement_theta_max      27.878
_cell_measurement_theta_min      0.407
_shelx_estimated_absorpt_T_max   0.347
_shelx_estimated_absorpt_T_min   0.302
_exptl_absorpt_coefficient_mu    5.833
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.5467
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2012/1 (Bruker,2012) was used for absorption correction. wR2(int) was 0.0780 before and 0.0498 after correction. The Ratio of minimum to maximum transmission is 0.7331. The λ/2 correction factor is 0.0015.'
_exptl_crystal_colour            blue
_exptl_crystal_colour_primary    blue
_exptl_crystal_density_diffrn    2.527
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1132
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.23
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0263
_diffrn_reflns_av_unetI/netI     0.0217
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            7375
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.244
_diffrn_reflns_theta_min         2.042
_diffrn_ambient_temperature      170.0(1)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1423
_reflns_number_total             1516
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.561
_refine_diff_density_min         -0.678
_refine_diff_density_rms         0.096
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     91
_refine_ls_number_reflns         1516
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0215
_refine_ls_R_factor_gt           0.0192
_refine_ls_restrained_S_all      1.067
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0152P)²+4.5168P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0430
_refine_ls_wR_factor_ref         0.0440
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I5 I 0.72811(2) 0.13895(2) 0.64866(2) 0.03251(9) Uani 1 1 d . . . . .
Cu1 Cu 0.39128(6) 0.5000 0.61454(4) 0.01807(12) Uani 1 2 d S T P . .
Cl1 Cl 0.43653(12) 0.5000 0.78035(8) 0.0257(2) Uani 1 2 d S T P . .
Cl1' Cl 0.30235(11) 0.5000 0.45154(7) 0.0192(2) Uani 1 2 d S T P . .
Cl2 Cl 0.05552(9) 0.38345(5) 0.62312(6) 0.03307(19) Uani 1 1 d . . . . .
N1 N 0.3756(3) 0.36018(15) 0.61908(17) 0.0201(5) Uani 1 1 d . . . . .
C2 C 0.2299(3) 0.31671(19) 0.6222(2) 0.0225(6) Uani 1 1 d . . . . .
C3 C 0.2152(4) 0.2228(2) 0.6266(2) 0.0292(7) Uani 1 1 d . . . . .
H3 H 0.1093 0.1945 0.6260 0.035 Uiso 1 1 calc R . . . .
C4 C 0.3577(4) 0.1706(2) 0.6319(2) 0.0295(7) Uani 1 1 d . . . . .
H4 H 0.3517 0.1057 0.6357 0.035 Uiso 1 1 calc R . . . .
C5 C 0.5090(3) 0.21452(19) 0.6315(2) 0.0226(6) Uani 1 1 d . . . . .
C6 C 0.5146(3) 0.30913(18) 0.6244(2) 0.0217(6) Uani 1 1 d . . . . .
H6 H 0.6191 0.3388 0.6232 0.026 Uiso 1 1 calc R . . . .


_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
I5 C5 2.093(3) . ?
Cu1 Cl1 2.2830(12) . ?
Cu1 Cl1' 2.6636(12) 5_666 ?
Cu1 Cl1' 2.3176(12) . ?
Cu1 N1 2.047(2) 6_565 ?
Cu1 N1 2.047(2) . ?
Cl1' Cu1 2.6637(12) 5_666 ?
Cl2 C2 1.714(3) . ?
N1 C2 1.340(4) . ?
N1 C6 1.348(4) . ?
C2 C3 1.379(4) . ?
C3 H3 0.9500 . ?
C3 C4 1.381(4) . ?
C4 H4 0.9500 . ?
C4 C5 1.382(4) . ?
C5 C6 1.386(4) . ?
C6 H6 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
Cl1 Cu1 Cl1' 102.48(5) . 5_666 ?
Cl1 Cu1 Cl1' 171.16(4) . . ?
Cl1' Cu1 Cl1' 86.37(4) . 5_666 ?
N1 Cu1 Cl1 88.74(7) 6_565 . ?
N1 Cu1 Cl1 88.74(7) . . ?
N1 Cu1 Cl1' 93.99(7) 6_565 5_666 ?
N1 Cu1 Cl1' 90.66(7) 6_565 . ?
N1 Cu1 Cl1' 90.66(7) . . ?
N1 Cu1 Cl1' 93.99(7) . 5_666 ?
N1 Cu1 N1 171.98(13) 6_565 . ?
Cu1 Cl1' Cu1 93.63(4) . 5_666 ?
C2 N1 Cu1 121.94(18) . . ?
C2 N1 C6 117.9(2) . . ?
C6 N1 Cu1 120.06(18) . . ?
N1 C2 Cl2 117.0(2) . . ?
N1 C2 C3 123.3(3) . . ?
C3 C2 Cl2 119.6(2) . . ?
C2 C3 H3 120.7 . . ?
C2 C3 C4 118.6(3) . . ?
C4 C3 H3 120.7 . . ?
C3 C4 H4 120.7 . . ?
C3 C4 C5 118.7(3) . . ?
C5 C4 H4 120.7 . . ?
C4 C5 I5 120.0(2) . . ?
C4 C5 C6 119.6(3) . . ?
C6 C5 I5 120.3(2) . . ?
N1 C6 C5 121.8(3) . . ?
N1 C6 H6 119.1 . . ?
C5 C6 H6 119.1 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
