# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2022

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

data_exp_1177
_database_code_depnum_ccdc_archive 'CCDC 2036515'
loop_
_audit_author_name
_audit_author_address
'Firas Awwadi'
;The University of Jordan
Jordan
;
_audit_update_record             
;
2020-10-11 deposited with the CCDC.	2022-09-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 trans-Bis(2,5-diiodopyridine)dibromocopper(II)  
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H6 Br2 Cu I4 N2'
_chemical_formula_weight         885.13

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/n 1'

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

_cell_length_a                   6.6555(8)
_cell_length_b                   8.5691(18)
_cell_length_c                   16.085(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.120(13)
_cell_angle_gamma                90.00
_cell_volume                     908.2(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1173
_cell_measurement_theta_min      3.0889
_cell_measurement_theta_max      29.1656

_exptl_crystal_description       plate
_exptl_crystal_colour            brown
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.09
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    3.237
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             782
_exptl_absorpt_coefficient_mu    12.389
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.25486
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.0534
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4005
_diffrn_reflns_av_R_equivalents  0.0668
_diffrn_reflns_av_sigmaI/netI    0.0875
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         3.17
_diffrn_reflns_theta_max         26.30
_reflns_number_total             1846
_reflns_number_gt                1340
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;

_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;

_computing_structure_solution    'shelxtl, Bruker,2002'
_computing_structure_refinement  'shelxtl, Bruker,2002'
_computing_molecular_graphics    'shelxtl, Bruker,2002'
_computing_publication_material  'shelxtl, Bruker,2002'

_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. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0235P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0087(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1846
_refine_ls_number_parameters     89
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0687
_refine_ls_R_factor_gt           0.0468
_refine_ls_wR_factor_ref         0.1023
_refine_ls_wR_factor_gt          0.0843
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_restrained_S_all      1.017
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
I5 I 0.85688(10) 0.89525(8) 0.26573(4) 0.0418(3) Uani 1 1 d . . .
I2 I 0.13188(10) 0.74897(7) 0.52310(4) 0.0371(3) Uani 1 1 d . . .
Br1 Br 0.71840(15) 0.61082(11) 0.61978(7) 0.0363(3) Uani 1 1 d . . .
Cu1 Cu 0.5000 0.5000 0.5000 0.0270(4) Uani 1 2 d S . .
N1 N 0.4933(11) 0.7015(8) 0.4395(5) 0.0247(17) Uani 1 1 d . . .
C5 C 0.6345(13) 0.8658(10) 0.3446(6) 0.023(2) Uani 1 1 d . . .
C4 C 0.4886(14) 0.9780(11) 0.3504(6) 0.036(2) Uani 1 1 d . . .
H4A H 0.4850 1.0698 0.3194 0.044 Uiso 1 1 calc R . .
C3 C 0.3463(14) 0.9488(10) 0.4047(6) 0.031(2) Uani 1 1 d . . .
H3A H 0.2489 1.0233 0.4124 0.038 Uiso 1 1 calc R . .
C2 C 0.3523(13) 0.8084(11) 0.4468(6) 0.028(2) Uani 1 1 d . . .
C6 C 0.6340(14) 0.7305(10) 0.3887(6) 0.031(2) Uani 1 1 d . . .
H6A H 0.7332 0.6560 0.3838 0.037 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
I5 0.0480(5) 0.0478(5) 0.0322(5) 0.0064(3) 0.0145(3) -0.0061(3)
I2 0.0357(4) 0.0415(5) 0.0361(5) 0.0027(3) 0.0118(3) 0.0021(3)
Br1 0.0392(6) 0.0389(6) 0.0304(6) -0.0016(4) 0.0032(5) -0.0042(4)
Cu1 0.0327(9) 0.0257(9) 0.0233(9) 0.0030(7) 0.0068(7) -0.0013(7)
N1 0.028(4) 0.022(4) 0.024(4) 0.004(3) 0.003(3) 0.001(3)
C5 0.024(5) 0.028(5) 0.018(5) 0.001(4) 0.003(4) -0.007(4)
C4 0.040(6) 0.035(6) 0.036(6) 0.011(5) 0.010(5) -0.007(5)
C3 0.042(6) 0.024(5) 0.030(6) 0.000(4) 0.010(5) 0.002(4)
C2 0.030(5) 0.036(5) 0.017(5) -0.001(4) 0.003(4) -0.003(4)
C6 0.030(5) 0.035(5) 0.027(6) -0.003(4) 0.002(4) -0.003(4)

_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 2.096(8) . ?
I2 C2 2.103(8) . ?
Br1 Cu1 2.4362(11) . ?
Cu1 N1 1.980(7) 3_666 ?
Cu1 N1 1.980(7) . ?
Cu1 Br1 2.4362(11) 3_666 ?
N1 C2 1.329(11) . ?
N1 C6 1.350(11) . ?
C5 C6 1.359(11) . ?
C5 C4 1.379(12) . ?
C4 C3 1.399(12) . ?
C4 H4A 0.9300 . ?
C3 C2 1.379(12) . ?
C3 H3A 0.9300 . ?
C6 H6A 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
N1 Cu1 N1 180.000(2) 3_666 . ?
N1 Cu1 Br1 89.0(2) 3_666 . ?
N1 Cu1 Br1 91.0(2) . . ?
N1 Cu1 Br1 91.0(2) 3_666 3_666 ?
N1 Cu1 Br1 89.0(2) . 3_666 ?
Br1 Cu1 Br1 180.0 . 3_666 ?
C2 N1 C6 119.1(8) . . ?
C2 N1 Cu1 121.7(6) . . ?
C6 N1 Cu1 119.3(6) . . ?
C6 C5 C4 120.4(8) . . ?
C6 C5 I5 118.2(7) . . ?
C4 C5 I5 121.4(6) . . ?
C5 C4 C3 117.6(8) . . ?
C5 C4 H4A 121.2 . . ?
C3 C4 H4A 121.2 . . ?
C2 C3 C4 119.2(8) . . ?
C2 C3 H3A 120.4 . . ?
C4 C3 H3A 120.4 . . ?
N1 C2 C3 122.0(8) . . ?
N1 C2 I2 116.4(6) . . ?
C3 C2 I2 121.6(6) . . ?
N1 C6 C5 121.7(8) . . ?
N1 C6 H6A 119.1 . . ?
C5 C6 H6A 119.1 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 Cu1 N1 C2 167(100) 3_666 . . . ?
Br1 Cu1 N1 C2 -90.1(7) . . . . ?
Br1 Cu1 N1 C2 89.9(7) 3_666 . . . ?
N1 Cu1 N1 C6 -12(100) 3_666 . . . ?
Br1 Cu1 N1 C6 90.7(7) . . . . ?
Br1 Cu1 N1 C6 -89.3(7) 3_666 . . . ?
C6 C5 C4 C3 1.8(14) . . . . ?
I5 C5 C4 C3 -179.9(7) . . . . ?
C5 C4 C3 C2 -2.7(14) . . . . ?
C6 N1 C2 C3 -0.7(14) . . . . ?
Cu1 N1 C2 C3 -179.8(7) . . . . ?
C6 N1 C2 I2 177.4(6) . . . . ?
Cu1 N1 C2 I2 -1.8(10) . . . . ?
C4 C3 C2 N1 2.2(14) . . . . ?
C4 C3 C2 I2 -175.7(7) . . . . ?
C2 N1 C6 C5 -0.3(14) . . . . ?
Cu1 N1 C6 C5 178.9(7) . . . . ?
C4 C5 C6 N1 -0.3(14) . . . . ?
I5 C5 C6 N1 -178.6(7) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        26.30
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         1.881
_refine_diff_density_min         -1.254
_refine_diff_density_rms         0.273
####################################################################### 
# 
# 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_exp1009
_database_code_depnum_ccdc_archive 'CCDC 2036517'
loop_
_audit_author_name
_audit_author_address
'Firas Awwadi'
;The University of Jordan
Jordan
;
_audit_update_record             
;
2020-10-11 deposited with the CCDC.	2022-09-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 trans-dichloro-bis(2,5-iodopyridine)copper(II)
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H6 Cl2 Cu I4 N2'
_chemical_formula_sum            'C10 H6 Cl2 Cu I4 N2'
_chemical_formula_weight         796.21

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 1 2/c 1'

loop_
_symmetry_equiv_pos_as_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                   8.7666(4)
_cell_length_b                   13.2248(5)
_cell_length_c                   14.7942(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.012(3)
_cell_angle_gamma                90.00
_cell_volume                     1714.92(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1555
_cell_measurement_theta_min      3.0745
_cell_measurement_theta_max      29.4403

_exptl_crystal_description       parallelepiped
_exptl_crystal_colour            brown
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.11
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    3.084
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1420
_exptl_absorpt_coefficient_mu    8.773
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.54416
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.0534
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            3731
_diffrn_reflns_av_R_equivalents  0.0272
_diffrn_reflns_av_sigmaI/netI    0.0389
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.08
_diffrn_reflns_theta_max         26.30
_reflns_number_total             1737
_reflns_number_gt                1483
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_structure_solution    'shelxtl, Bruker,2002'
_computing_structure_refinement  'shelxtl, Bruker,2002'
_computing_molecular_graphics    'shelxtl, Bruker,2002'
_computing_publication_material  'shelxtl, Bruker,2002'

_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. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0218P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.00064(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1737
_refine_ls_number_parameters     88
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0367
_refine_ls_R_factor_gt           0.0290
_refine_ls_wR_factor_ref         0.0618
_refine_ls_wR_factor_gt          0.0583
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.040
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
I5 I -0.34686(4) 1.05742(2) 0.39375(2) 0.03746(14) Uani 1 1 d . . .
I2 I -0.65709(5) 1.43299(3) 0.65290(2) 0.04213(14) Uani 1 1 d . . .
Cu1 Cu -0.5000 1.21798(5) 0.7500 0.0245(2) Uani 1 2 d S . .
Cl1 Cl -0.26235(14) 1.15366(10) 0.76173(8) 0.0347(3) Uani 1 1 d . . .
N1 N -0.4919(5) 1.2431(3) 0.6156(2) 0.0248(9) Uani 1 1 d . . .
C6 C -0.4288(6) 1.1717(3) 0.5636(3) 0.0270(11) Uani 1 1 d . . .
H6A H -0.3804 1.1171 0.5914 0.032 Uiso 1 1 calc R . .
C4 C -0.5012(6) 1.2577(3) 0.4287(3) 0.0358(13) Uani 1 1 d . . .
H4A H -0.5044 1.2624 0.3660 0.043 Uiso 1 1 calc R . .
C2 C -0.5598(6) 1.3213(3) 0.5735(3) 0.0266(11) Uani 1 1 d . . .
C3 C -0.5644(7) 1.3316(4) 0.4807(3) 0.0382(14) Uani 1 1 d . . .
H3A H -0.6098 1.3879 0.4539 0.046 Uiso 1 1 calc R . .
C5 C -0.4331(6) 1.1764(3) 0.4706(3) 0.0266(11) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
I5 0.0419(3) 0.0440(2) 0.0267(2) -0.00743(14) 0.00612(16) 0.00736(16)
I2 0.0508(3) 0.0464(2) 0.0293(2) -0.00439(15) 0.00133(18) 0.01878(17)
Cu1 0.0292(5) 0.0297(4) 0.0147(4) 0.000 0.0011(3) 0.000
Cl1 0.0328(8) 0.0463(7) 0.0251(7) -0.0026(5) -0.0007(5) 0.0067(6)
N1 0.026(2) 0.028(2) 0.020(2) -0.0001(17) 0.0002(17) -0.0009(18)
C6 0.032(3) 0.027(2) 0.023(3) 0.0046(19) 0.003(2) 0.004(2)
C4 0.050(4) 0.043(3) 0.014(2) 0.004(2) -0.003(2) 0.008(3)
C2 0.029(3) 0.028(2) 0.022(2) -0.002(2) 0.002(2) 0.002(2)
C3 0.055(4) 0.036(3) 0.024(3) 0.010(2) 0.000(3) 0.016(3)
C5 0.026(3) 0.033(2) 0.020(2) -0.004(2) 0.001(2) -0.002(2)

_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 2.091(5) . ?
I2 C2 2.079(5) . ?
Cu1 N1 2.018(4) . ?
Cu1 N1 2.018(4) 2_456 ?
Cu1 Cl1 2.2542(13) 2_456 ?
Cu1 Cl1 2.2542(13) . ?
N1 C2 1.342(5) . ?
N1 C6 1.344(6) . ?
C6 C5 1.376(6) . ?
C6 H6A 0.9300 . ?
C4 C3 1.367(7) . ?
C4 C5 1.372(6) . ?
C4 H4A 0.9300 . ?
C2 C3 1.378(6) . ?
C3 H3A 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
N1 Cu1 N1 161.0(2) . 2_456 ?
N1 Cu1 Cl1 92.00(12) . 2_456 ?
N1 Cu1 Cl1 95.13(12) 2_456 2_456 ?
N1 Cu1 Cl1 95.13(12) . . ?
N1 Cu1 Cl1 92.00(12) 2_456 . ?
Cl1 Cu1 Cl1 135.67(8) 2_456 . ?
C2 N1 C6 117.3(4) . . ?
C2 N1 Cu1 124.2(3) . . ?
C6 N1 Cu1 118.1(3) . . ?
N1 C6 C5 122.5(4) . . ?
N1 C6 H6A 118.8 . . ?
C5 C6 H6A 118.8 . . ?
C3 C4 C5 118.9(4) . . ?
C3 C4 H4A 120.6 . . ?
C5 C4 H4A 120.6 . . ?
N1 C2 C3 122.9(4) . . ?
N1 C2 I2 117.9(3) . . ?
C3 C2 I2 119.2(3) . . ?
C4 C3 C2 119.0(4) . . ?
C4 C3 H3A 120.5 . . ?
C2 C3 H3A 120.5 . . ?
C4 C5 C6 119.4(4) . . ?
C4 C5 I5 120.2(3) . . ?
C6 C5 I5 120.4(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
N1 Cu1 N1 C2 -33.8(4) 2_456 . . . ?
Cl1 Cu1 N1 C2 78.4(4) 2_456 . . . ?
Cl1 Cu1 N1 C2 -145.4(4) . . . . ?
N1 Cu1 N1 C6 153.7(4) 2_456 . . . ?
Cl1 Cu1 N1 C6 -94.1(4) 2_456 . . . ?
Cl1 Cu1 N1 C6 42.1(4) . . . . ?
C2 N1 C6 C5 -0.5(7) . . . . ?
Cu1 N1 C6 C5 172.5(4) . . . . ?
C6 N1 C2 C3 -1.2(7) . . . . ?
Cu1 N1 C2 C3 -173.8(4) . . . . ?
C6 N1 C2 I2 -179.7(3) . . . . ?
Cu1 N1 C2 I2 7.8(5) . . . . ?
C5 C4 C3 C2 -1.0(8) . . . . ?
N1 C2 C3 C4 2.0(8) . . . . ?
I2 C2 C3 C4 -179.6(4) . . . . ?
C3 C4 C5 C6 -0.6(8) . . . . ?
C3 C4 C5 I5 176.3(4) . . . . ?
N1 C6 C5 C4 1.4(8) . . . . ?
N1 C6 C5 I5 -175.4(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        26.30
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.669
_refine_diff_density_min         -0.752
_refine_diff_density_rms         0.141
####################################################################### 
# 
# 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_exp_1540
_database_code_depnum_ccdc_archive 'CCDC 2036516'
loop_
_audit_author_name
_audit_author_address
'Firas Awwadi'
;The University of Jordan
Jordan
;
_audit_update_record             
;
2020-10-11 deposited with the CCDC.	2022-09-09 downloaded from the CCDC.
;

_audit_creation_method           
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H6 Br2 Cu I4 N2'
_chemical_formula_weight         885.13

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.6977(4)
_cell_length_b                   8.5845(6)
_cell_length_c                   8.6691(11)
_cell_angle_alpha                71.645(10)
_cell_angle_beta                 74.675(9)
_cell_angle_gamma                89.946(6)
_cell_volume                     454.41(7)
_cell_formula_units_Z            1
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1122
_cell_measurement_theta_min      3.1601
_cell_measurement_theta_max      29.2947

_exptl_crystal_description       needle
_exptl_crystal_colour            brown
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.07
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    3.234
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             391
_exptl_absorpt_coefficient_mu    12.380
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.31505
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.0534
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            3382
_diffrn_reflns_av_R_equivalents  0.0300
_diffrn_reflns_av_sigmaI/netI    0.0551
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         3.17
_diffrn_reflns_theta_max         26.30
_reflns_number_total             1850
_reflns_number_gt                1481
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;

_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;

_computing_structure_solution    'shelxtl, Bruker,2002'
_computing_structure_refinement  'shelxtl, Bruker,2002'
_computing_molecular_graphics    'shelxtl, Bruker,2002'
_computing_publication_material  'shelxtl, Bruker,2002'

_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. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0579P)²+0.1059P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1850
_refine_ls_number_parameters     88
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0631
_refine_ls_R_factor_gt           0.0490
_refine_ls_wR_factor_ref         0.1299
_refine_ls_wR_factor_gt          0.1216
_refine_ls_goodness_of_fit_ref   1.137
_refine_ls_restrained_S_all      1.137
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
I2 I 0.39351(10) 0.76020(8) 0.45284(9) 0.0385(2) Uani 1 1 d . . .
I5 I -0.58833(11) 0.75754(9) 0.96540(9) 0.0438(3) Uani 1 1 d . . .
Cu1 Cu 0.0000 0.5000 0.5000 0.0277(4) Uani 1 2 d S . .
Br1 Br 0.09415(16) 0.31135(13) 0.74114(13) 0.0373(3) Uani 1 1 d . . .
N1 N -0.0508(12) 0.6638(9) 0.6187(10) 0.0273(17) Uani 1 1 d . . .
C5 C -0.2876(14) 0.7730(12) 0.8071(12) 0.030(2) Uani 1 1 d . . .
C2 C 0.0979(14) 0.7746(11) 0.6039(12) 0.029(2) Uani 1 1 d . . .
C4 C -0.1304(16) 0.8870(12) 0.7924(13) 0.037(3) Uani 1 1 d . . .
H4A H -0.1565 0.9593 0.8543 0.044 Uiso 1 1 calc R . .
C6 C -0.2435(14) 0.6624(11) 0.7201(12) 0.029(2) Uani 1 1 d . . .
H6A H -0.3480 0.5852 0.7312 0.035 Uiso 1 1 calc R . .
C3 C 0.0628(15) 0.8919(12) 0.6861(13) 0.036(2) Uani 1 1 d . . .
H3A H 0.1678 0.9714 0.6692 0.043 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
I2 0.0274(4) 0.0435(5) 0.0428(5) -0.0181(4) -0.0021(3) 0.0005(3)
I5 0.0385(4) 0.0505(5) 0.0371(5) -0.0184(4) 0.0031(3) 0.0122(3)
Cu1 0.0256(8) 0.0278(9) 0.0320(10) -0.0166(8) -0.0033(7) 0.0047(7)
Br1 0.0380(6) 0.0378(6) 0.0355(6) -0.0135(5) -0.0074(5) 0.0097(5)
N1 0.027(4) 0.033(4) 0.022(4) -0.012(4) -0.004(3) 0.006(3)
C5 0.028(5) 0.031(5) 0.028(5) -0.010(4) -0.003(4) 0.009(4)
C2 0.031(5) 0.030(5) 0.031(5) -0.015(4) -0.011(4) 0.013(4)
C4 0.053(7) 0.029(5) 0.033(6) -0.019(5) -0.010(5) 0.007(5)
C6 0.021(5) 0.029(5) 0.038(6) -0.014(5) -0.008(4) 0.005(4)
C3 0.032(6) 0.032(6) 0.045(7) -0.012(5) -0.011(5) 0.001(4)

_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
I2 C2 2.093(9) . ?
I5 C5 2.093(9) . ?
Cu1 N1 1.969(7) . ?
Cu1 N1 1.969(7) 2_566 ?
Cu1 Br1 2.4399(12) 2_566 ?
Cu1 Br1 2.4399(12) . ?
N1 C2 1.331(12) . ?
N1 C6 1.354(11) . ?
C5 C6 1.375(12) . ?
C5 C4 1.391(14) . ?
C2 C3 1.393(12) . ?
C4 C3 1.367(14) . ?
C4 H4A 0.9300 . ?
C6 H6A 0.9300 . ?
C3 H3A 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
N1 Cu1 N1 180.000(1) . 2_566 ?
N1 Cu1 Br1 90.5(2) . 2_566 ?
N1 Cu1 Br1 89.5(2) 2_566 2_566 ?
N1 Cu1 Br1 89.5(2) . . ?
N1 Cu1 Br1 90.5(2) 2_566 . ?
Br1 Cu1 Br1 180.0 2_566 . ?
C2 N1 C6 118.9(7) . . ?
C2 N1 Cu1 122.3(6) . . ?
C6 N1 Cu1 118.8(6) . . ?
C6 C5 C4 119.3(8) . . ?
C6 C5 I5 118.5(7) . . ?
C4 C5 I5 122.2(6) . . ?
N1 C2 C3 122.7(8) . . ?
N1 C2 I2 116.1(6) . . ?
C3 C2 I2 121.2(7) . . ?
C3 C4 C5 119.5(8) . . ?
C3 C4 H4A 120.2 . . ?
C5 C4 H4A 120.2 . . ?
N1 C6 C5 121.3(8) . . ?
N1 C6 H6A 119.3 . . ?
C5 C6 H6A 119.3 . . ?
C4 C3 C2 118.1(9) . . ?
C4 C3 H3A 120.9 . . ?
C2 C3 H3A 120.9 . . ?

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
N1 Cu1 N1 C2 125(100) 2_566 . . . ?
Br1 Cu1 N1 C2 -90.5(8) 2_566 . . . ?
Br1 Cu1 N1 C2 89.5(8) . . . . ?
N1 Cu1 N1 C6 -54(100) 2_566 . . . ?
Br1 Cu1 N1 C6 90.2(7) 2_566 . . . ?
Br1 Cu1 N1 C6 -89.8(7) . . . . ?
C6 N1 C2 C3 -1.3(15) . . . . ?
Cu1 N1 C2 C3 179.4(8) . . . . ?
C6 N1 C2 I2 177.4(7) . . . . ?
Cu1 N1 C2 I2 -2.0(10) . . . . ?
C6 C5 C4 C3 2.9(16) . . . . ?
I5 C5 C4 C3 -179.6(8) . . . . ?
C2 N1 C6 C5 0.1(15) . . . . ?
Cu1 N1 C6 C5 179.5(8) . . . . ?
C4 C5 C6 N1 -0.9(16) . . . . ?
I5 C5 C6 N1 -178.6(7) . . . . ?
C5 C4 C3 C2 -3.9(17) . . . . ?
N1 C2 C3 C4 3.2(17) . . . . ?
I2 C2 C3 C4 -175.4(8) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        26.30
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         1.992
_refine_diff_density_min         -0.941
_refine_diff_density_rms         0.261
####################################################################### 
# 
# 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_exp_1112
_database_code_depnum_ccdc_archive 'CCDC 2036518'
loop_
_audit_author_name
_audit_author_address
'Firas Awwadi'
;The University of Jordan
Jordan
;
_audit_update_record             
;
2020-10-11 deposited with the CCDC.	2022-09-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 trans-bis(2,5-diiodopyridine)dichlorocopper(II) 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H6 Cl2 Cu I4 N2'
_chemical_formula_weight         796.21

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.679(4)
_cell_length_b                   8.508(7)
_cell_length_c                   8.869(6)
_cell_angle_alpha                70.54(7)
_cell_angle_beta                 72.42(6)
_cell_angle_gamma                88.46(6)
_cell_volume                     451.5(5)
_cell_formula_units_Z            1
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1189
_cell_measurement_theta_min      2.9233
_cell_measurement_theta_max      29.3730

_exptl_crystal_description       cube
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.928
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             355
_exptl_absorpt_coefficient_mu    8.331
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.51068
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.0534
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            3321
_diffrn_reflns_av_R_equivalents  0.0319
_diffrn_reflns_av_sigmaI/netI    0.0596
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.93
_diffrn_reflns_theta_max         26.30
_reflns_number_total             1835
_reflns_number_gt                1390
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;

_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;

_computing_structure_solution    'shelxtl, Bruker,2002'
_computing_structure_refinement  'shelxtl, Bruker,2002'
_computing_molecular_graphics    'shelxtl, Bruker,2002'
_computing_publication_material  'shelxtl, Bruker,2002'

_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. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0205P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0119(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1835
_refine_ls_number_parameters     89
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0541
_refine_ls_R_factor_gt           0.0376
_refine_ls_wR_factor_ref         0.0776
_refine_ls_wR_factor_gt          0.0654
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_restrained_S_all      1.021
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
I2 I -0.09555(7) 1.25542(6) 0.95160(7) 0.04028(19) Uani 1 1 d . . .
Cu1 Cu -0.5000 1.0000 1.0000 0.0290(3) Uani 1 2 d S . .
C5 C -0.7897(11) 1.2776(8) 1.3080(9) 0.0326(17) Uani 1 1 d . . .
N1 N -0.5476(8) 1.1661(7) 1.1170(7) 0.0289(13) Uani 1 1 d . . .
C4 C -0.6338(12) 1.3911(9) 1.2895(10) 0.042(2) Uani 1 1 d . . .
H4A H -0.6618 1.4671 1.3466 0.051 Uiso 1 1 calc R . .
C3 C -0.4353(11) 1.3894(9) 1.1841(10) 0.0395(19) Uani 1 1 d . . .
H3A H -0.3276 1.4661 1.1682 0.047 Uiso 1 1 calc R . .
C2 C -0.3951(10) 1.2745(8) 1.1021(9) 0.0314(16) Uani 1 1 d . . .
C6 C -0.7447(10) 1.1675(8) 1.2206(8) 0.0290(16) Uani 1 1 d . . .
H6A H -0.8517 1.0923 1.2326 0.035 Uiso 1 1 calc R . .
Cl1 Cl -0.5792(3) 1.1884(2) 0.7796(2) 0.0394(5) Uani 1 1 d . . .
I5 I -1.09643(8) 1.26105(6) 1.46977(7) 0.0459(2) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
I2 0.0304(3) 0.0430(3) 0.0433(4) -0.0179(3) -0.0018(2) 0.0003(2)
Cu1 0.0286(6) 0.0281(7) 0.0295(7) -0.0162(6) -0.0006(6) 0.0014(5)
C5 0.038(4) 0.033(4) 0.026(4) -0.016(4) -0.003(3) 0.014(3)
N1 0.026(3) 0.028(3) 0.030(3) -0.014(3) 0.000(3) 0.004(3)
C4 0.059(5) 0.035(4) 0.043(5) -0.026(4) -0.018(4) 0.014(4)
C3 0.036(4) 0.034(4) 0.053(5) -0.024(4) -0.010(4) 0.001(3)
C2 0.034(4) 0.027(4) 0.035(4) -0.014(4) -0.009(3) 0.005(3)
C6 0.025(4) 0.030(4) 0.032(4) -0.013(4) -0.006(3) 0.002(3)
Cl1 0.0427(11) 0.0371(10) 0.0378(11) -0.0157(10) -0.0088(9) 0.0086(9)
I5 0.0436(3) 0.0481(4) 0.0375(4) -0.0184(3) 0.0033(3) 0.0107(3)

_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
I2 C2 2.080(7) . ?
Cu1 N1 1.982(5) 2_477 ?
Cu1 N1 1.982(5) . ?
Cu1 Cl1 2.272(3) . ?
Cu1 Cl1 2.272(3) 2_477 ?
C5 C4 1.375(10) . ?
C5 C6 1.377(8) . ?
C5 I5 2.093(7) . ?
N1 C2 1.340(8) . ?
N1 C6 1.361(7) . ?
C4 C3 1.375(9) . ?
C4 H4A 0.9300 . ?
C3 C2 1.377(8) . ?
C3 H3A 0.9300 . ?
C6 H6A 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
N1 Cu1 N1 180.000(2) 2_477 . ?
N1 Cu1 Cl1 90.33(18) 2_477 . ?
N1 Cu1 Cl1 89.67(18) . . ?
N1 Cu1 Cl1 89.67(18) 2_477 2_477 ?
N1 Cu1 Cl1 90.33(18) . 2_477 ?
Cl1 Cu1 Cl1 180.00(8) . 2_477 ?
C4 C5 C6 119.7(6) . . ?
C4 C5 I5 122.4(5) . . ?
C6 C5 I5 117.9(5) . . ?
C2 N1 C6 118.4(5) . . ?
C2 N1 Cu1 123.4(4) . . ?
C6 N1 Cu1 118.2(4) . . ?
C5 C4 C3 118.3(6) . . ?
C5 C4 H4A 120.9 . . ?
C3 C4 H4A 120.9 . . ?
C4 C3 C2 120.3(7) . . ?
C4 C3 H3A 119.9 . . ?
C2 C3 H3A 119.9 . . ?
N1 C2 C3 121.6(6) . . ?
N1 C2 I2 115.9(4) . . ?
C3 C2 I2 122.5(5) . . ?
N1 C6 C5 121.7(6) . . ?
N1 C6 H6A 119.2 . . ?
C5 C6 H6A 119.2 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 Cu1 N1 C2 57(100) 2_477 . . . ?
Cl1 Cu1 N1 C2 -90.7(6) . . . . ?
Cl1 Cu1 N1 C2 89.3(6) 2_477 . . . ?
N1 Cu1 N1 C6 -122(100) 2_477 . . . ?
Cl1 Cu1 N1 C6 90.7(5) . . . . ?
Cl1 Cu1 N1 C6 -89.3(5) 2_477 . . . ?
C6 C5 C4 C3 -0.7(11) . . . . ?
I5 C5 C4 C3 178.0(5) . . . . ?
C5 C4 C3 C2 -1.0(11) . . . . ?
C6 N1 C2 C3 -2.2(10) . . . . ?
Cu1 N1 C2 C3 179.2(5) . . . . ?
C6 N1 C2 I2 176.8(5) . . . . ?
Cu1 N1 C2 I2 -1.7(8) . . . . ?
C4 C3 C2 N1 2.5(11) . . . . ?
C4 C3 C2 I2 -176.5(6) . . . . ?
C2 N1 C6 C5 0.5(10) . . . . ?
Cu1 N1 C6 C5 179.1(5) . . . . ?
C4 C5 C6 N1 1.0(11) . . . . ?
I5 C5 C6 N1 -177.8(5) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        26.30
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         1.165
_refine_diff_density_min         -0.945
_refine_diff_density_rms         0.183
