# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2023

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

data_exp_1497
_database_code_depnum_ccdc_archive 'CCDC 2224781'
loop_
_audit_author_name
_audit_author_address
Fandi
;The University of Jordan
Jordan
;
_audit_update_record             
;
2022-12-06 deposited with the CCDC.	2023-03-28 downloaded from the CCDC.
;
_audit_creation_date             2022-08-20
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_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          ?
_chemical_oxdiff_formula         'Cu Cl C H I N'
_chemical_oxdiff_usercomment     'Cucl2 2i5clpy acn manal hot'
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'

_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                   6.6375(11)
_cell_length_b                   8.1893(14)
_cell_length_c                   8.4260(13)
_cell_angle_alpha                69.401(15)
_cell_angle_beta                 88.117(13)
_cell_angle_gamma                73.592(15)
_cell_volume                     410.14(13)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    1227
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.1004
_cell_measurement_theta_min      3.0390
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    5.732
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.34228
_exptl_absorpt_correction_type   multi-scan
_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_absorpt_special_details   ?
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    2.483
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             283
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0400
_diffrn_reflns_av_unetI/netI     0.0576
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.844
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            3186
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.844
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.168
_diffrn_reflns_theta_min         3.046
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.0534
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.844
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   27.00   53.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -15.2878   38.0000  -30.0000 26

#__ type_ start__ end____ width___ exp.time_
  2 omega   -1.00   82.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       15.9128   77.0000 -180.0000 83

#__ type_ start__ end____ width___ exp.time_
  3 omega   45.00   78.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       15.9128   38.0000 -120.0000 33

#__ type_ start__ end____ width___ exp.time_
  4 omega  -49.00   43.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       15.9128  -77.0000  -60.0000 92

#__ type_ start__ end____ width___ exp.time_
  5 omega  -11.00   82.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       15.9128   77.0000   60.0000 93
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0414375000
_diffrn_orient_matrix_UB_12      0.0488403000
_diffrn_orient_matrix_UB_13      -0.0743501000
_diffrn_orient_matrix_UB_21      -0.0629621000
_diffrn_orient_matrix_UB_22      0.0833369000
_diffrn_orient_matrix_UB_23      0.0055657000
_diffrn_orient_matrix_UB_31      0.0824207000
_diffrn_orient_matrix_UB_32      0.0012121000
_diffrn_orient_matrix_UB_33      0.0506377000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1544
_reflns_number_total             1871
_reflns_odcompleteness_completeness 99.58
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_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_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.710
_refine_diff_density_min         -0.985
_refine_diff_density_rms         0.165
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     88
_refine_ls_number_reflns         1871
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0497
_refine_ls_R_factor_gt           0.0390
_refine_ls_restrained_S_all      1.058
_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)+(0.0343P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0844
_refine_ls_wR_factor_ref         0.0910
_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), C3(H3), C4(H4)
;
_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
I2 I 0.09956(5) 0.54256(6) 0.24530(4) 0.03997(16) Uani 1 1 d . . . . .
Cu1 Cu 0.500000 0.500000 0.500000 0.0271(2) Uani 1 2 d S . P . .
Cl1 Cl 0.5861(2) 0.7349(2) 0.30328(16) 0.0393(3) Uani 1 1 d . . . . .
Cl5 Cl 1.0474(3) 0.0335(2) 0.2316(2) 0.0553(5) Uani 1 1 d . . . . .
N1 N 0.5504(6) 0.3635(6) 0.3408(5) 0.0280(10) Uani 1 1 d . . . . .
C2 C 0.3995(8) 0.3803(8) 0.2310(6) 0.0305(12) Uani 1 1 d . . . . .
C6 C 0.7468(8) 0.2543(8) 0.3397(6) 0.0333(13) Uani 1 1 d . . . . .
H6 H 0.852951 0.239730 0.417137 0.040 Uiso 1 1 calc R U . . .
C5 C 0.7913(9) 0.1655(8) 0.2269(7) 0.0355(13) Uani 1 1 d . . . . .
C3 C 0.4380(9) 0.2897(9) 0.1160(7) 0.0412(15) Uani 1 1 d . . . . .
H3 H 0.329688 0.301799 0.041689 0.049 Uiso 1 1 calc R U . . .
C4 C 0.6380(10) 0.1823(9) 0.1136(7) 0.0400(14) Uani 1 1 d . . . . .
H4 H 0.668122 0.122386 0.036386 0.048 Uiso 1 1 calc R U . . .

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 0.0337(2) 0.0479(3) 0.0391(2) -0.01904(19) 0.00221(14) -0.00861(18)
Cu1 0.0292(5) 0.0311(6) 0.0242(4) -0.0146(4) 0.0039(3) -0.0078(4)
Cl1 0.0498(8) 0.0370(9) 0.0336(7) -0.0139(6) 0.0095(5) -0.0153(7)
Cl5 0.0530(10) 0.0483(11) 0.0546(9) -0.0226(8) 0.0122(7) 0.0050(8)
N1 0.027(2) 0.027(3) 0.035(2) -0.0171(19) 0.0080(16) -0.0086(19)
C2 0.037(3) 0.032(3) 0.028(3) -0.014(2) 0.009(2) -0.014(3)
C6 0.036(3) 0.031(3) 0.030(3) -0.010(2) 0.004(2) -0.008(3)
C5 0.042(3) 0.026(3) 0.035(3) -0.012(2) 0.014(2) -0.005(3)
C3 0.045(3) 0.054(4) 0.038(3) -0.026(3) 0.006(2) -0.023(3)
C4 0.057(4) 0.040(4) 0.036(3) -0.028(3) 0.018(2) -0.018(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 2.085(5) . ?
Cu1 Cl1 2.2563(15) 2_666 ?
Cu1 Cl1 2.2563(14) . ?
Cu1 N1 1.994(4) . ?
Cu1 N1 1.994(4) 2_666 ?
Cl5 C5 1.731(6) . ?
N1 C2 1.331(6) . ?
N1 C6 1.359(7) . ?
C2 C3 1.391(8) . ?
C6 H6 0.9300 . ?
C6 C5 1.366(8) . ?
C5 C4 1.363(8) . ?
C3 H3 0.9300 . ?
C3 C4 1.374(8) . ?
C4 H4 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(7) . 2_666 ?
N1 Cu1 Cl1 89.57(13) . 2_666 ?
N1 Cu1 Cl1 89.57(13) 2_666 . ?
N1 Cu1 Cl1 90.43(13) 2_666 2_666 ?
N1 Cu1 Cl1 90.43(13) . . ?
N1 Cu1 N1 180.0 2_666 . ?
C2 N1 Cu1 122.2(3) . . ?
C2 N1 C6 118.6(5) . . ?
C6 N1 Cu1 119.2(4) . . ?
N1 C2 I2 116.6(4) . . ?
N1 C2 C3 121.8(5) . . ?
C3 C2 I2 121.6(4) . . ?
N1 C6 H6 119.4 . . ?
N1 C6 C5 121.2(5) . . ?
C5 C6 H6 119.4 . . ?
C6 C5 Cl5 118.0(5) . . ?
C4 C5 Cl5 121.4(4) . . ?
C4 C5 C6 120.6(5) . . ?
C2 C3 H3 120.4 . . ?
C4 C3 C2 119.2(5) . . ?
C4 C3 H3 120.4 . . ?
C5 C4 C3 118.5(5) . . ?
C5 C4 H4 120.7 . . ?
C3 C4 H4 120.7 . . ?

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
I2 C2 C3 C4 -179.0(4) . . . . ?
Cu1 N1 C2 I2 -4.4(5) . . . . ?
Cu1 N1 C2 C3 177.6(4) . . . . ?
Cu1 N1 C6 C5 -176.6(4) . . . . ?
Cl5 C5 C4 C3 -179.7(5) . . . . ?
N1 C2 C3 C4 -1.1(9) . . . . ?
N1 C6 C5 Cl5 178.5(4) . . . . ?
N1 C6 C5 C4 -0.9(9) . . . . ?
C2 N1 C6 C5 1.2(8) . . . . ?
C2 C3 C4 C5 1.3(9) . . . . ?
C6 N1 C2 I2 177.9(4) . . . . ?
C6 N1 C2 C3 -0.2(8) . . . . ?
C6 C5 C4 C3 -0.3(9) . . . . ?

_shelx_res_file                  
;
TITL exp_1497_a.res in P-1
    exp_1497.res
    created by SHELXL-2018/3 at 01:27:41 on 20-Aug-2022
REM Old TITL exp_1497 in P1 #1
REM SHELXT solution in P-1: R1 0.086, Rweak 0.008, Alpha 0.031
REM <I/s> 0.000 for 0 systematic absences, Orientation as input
REM Formula found by SHELXT: C10 N2 Cl4 Cu I2
CELL 0.71073 6.6375 8.1893 8.426 69.401 88.117 73.592
ZERR 1 0.0011 0.0014 0.0013 0.015 0.013 0.015
LATT 1
SFAC C H N Cl Cu I
UNIT 10 6 2 4 1 2

L.S. 4 0 0
PLAN  4
CONF
BOND
list 4
MORE -1
BOND $H
fmap 2
acta
REM <olex2.extras>
REM <HklSrc "%.\\exp_1497.hkl">
REM </olex2.extras>

WGHT    0.034300
FVAR       0.68072
I2    6    0.099558    0.542557    0.245304    11.00000    0.03372    0.04793 =
         0.03912   -0.01904    0.00221   -0.00861
CU1   5    0.500000    0.500000    0.500000    10.50000    0.02923    0.03112 =
         0.02415   -0.01461    0.00390   -0.00778
CL1   4    0.586118    0.734929    0.303285    11.00000    0.04976    0.03699 =
         0.03356   -0.01392    0.00952   -0.01534
CL5   4    1.047418    0.033546    0.231566    11.00000    0.05299    0.04827 =
         0.05457   -0.02257    0.01216    0.00501
N1    3    0.550400    0.363532    0.340755    11.00000    0.02671    0.02717 =
         0.03530   -0.01712    0.00804   -0.00856
C2    1    0.399529    0.380262    0.230987    11.00000    0.03695    0.03206 =
         0.02804   -0.01449    0.00916   -0.01417
C6    1    0.746797    0.254291    0.339654    11.00000    0.03588    0.03121 =
         0.03008   -0.00957    0.00414   -0.00766
AFIX  43
H6    2    0.852951    0.239730    0.417137    11.00000   -1.20000
AFIX   0
C5    1    0.791277    0.165466    0.226924    11.00000    0.04228    0.02596 =
         0.03463   -0.01184    0.01410   -0.00455
C3    1    0.438015    0.289736    0.116015    11.00000    0.04540    0.05411 =
         0.03758   -0.02639    0.00557   -0.02259
AFIX  43
H3    2    0.329688    0.301799    0.041689    11.00000   -1.20000
AFIX   0
C4    1    0.638001    0.182301    0.113618    11.00000    0.05727    0.04008 =
         0.03631   -0.02811    0.01781   -0.01789
AFIX  43
H4    2    0.668122    0.122386    0.036386    11.00000   -1.20000
AFIX   0
HKLF 4




REM  exp_1497_a.res in P-1
REM wR2 = 0.0910, GooF = S = 1.058, Restrained GooF = 1.058 for all data
REM R1 = 0.0390 for 1544 Fo > 4sig(Fo) and 0.0497 for all 1871 data
REM 88 parameters refined using 0 restraints

END

WGHT      0.0341      0.0000

REM Highest difference peak  0.710,  deepest hole -0.985,  1-sigma level  0.165
Q1    1   0.2062  0.4804  0.0947  11.00000  0.05    0.71
Q2    1   0.0913  0.5456  0.4017  11.00000  0.05    0.62
Q3    1   0.5837  0.4475  0.4034  11.00000  0.05    0.55
Q4    1  -0.0733  0.5379  0.2795  11.00000  0.05    0.54
;
_shelx_res_checksum              82272
_olex2_date_sample_data_collection 2014-12-16
_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_exp_1248
_database_code_depnum_ccdc_archive 'CCDC 2224786'
loop_
_audit_author_name
_audit_author_address
Fandi
;The University of Jordan
Jordan
;
_audit_update_record             
;
2022-12-06 deposited with the CCDC.	2023-03-28 downloaded from the CCDC.
;
_audit_creation_date             2022-08-20
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C10 H6 Br4 Cu I2 N2'
_chemical_formula_sum            'C10 H6 Br4 Cu I2 N2'
_chemical_formula_weight         791.15
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N I Br Cu'
_chemical_oxdiff_usercomment     'dr firas cubr2 2I 5Br py 1:a acn'
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'

_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/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_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                   6.5988(12)
_cell_length_b                   8.5468(7)
_cell_length_c                   15.443(12)
_cell_angle_alpha                90
_cell_angle_beta                 98.57(4)
_cell_angle_gamma                90
_cell_volume                     861.3(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1448
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.4026
_cell_measurement_theta_min      3.1997
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    14.118
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.36082
_exptl_absorpt_correction_type   multi-scan
_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_absorpt_special_details   ?
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    3.051
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       parallelepiped
_exptl_crystal_F_000             710
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0256
_diffrn_reflns_av_unetI/netI     0.0429
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.838
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            4084
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.838
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.466
_diffrn_reflns_theta_min         3.207
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.0534
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.838
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -51.00   40.00   1.0000   12.5400
omega____ theta____ kappa____ phi______ frames
    -       15.9128  -77.0000    0.0000 91

#__ type_ start__ end____ width___ exp.time_
  2 omega    0.00   26.00   1.0000   12.5400
omega____ theta____ kappa____ phi______ frames
    -       15.9128   45.0000  -23.0000 26

#__ type_ start__ end____ width___ exp.time_
  3 omega  -10.00   82.00   1.0000   12.5400
omega____ theta____ kappa____ phi______ frames
    -       15.9128   77.0000  120.0000 92
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.1052336000
_diffrn_orient_matrix_UB_12      -0.0075473000
_diffrn_orient_matrix_UB_13      0.0040238000
_diffrn_orient_matrix_UB_21      -0.0223433000
_diffrn_orient_matrix_UB_22      0.0681379000
_diffrn_orient_matrix_UB_23      -0.0258860000
_diffrn_orient_matrix_UB_31      -0.0156312000
_diffrn_orient_matrix_UB_32      -0.0467620000
_diffrn_orient_matrix_UB_33      -0.0384213000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1627
_reflns_number_total             1996
_reflns_odcompleteness_completeness 99.74
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_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_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.938
_refine_diff_density_min         -0.758
_refine_diff_density_rms         0.165
_refine_ls_extinction_coef       0.0064(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     89
_refine_ls_number_reflns         1996
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0462
_refine_ls_R_factor_gt           0.0338
_refine_ls_restrained_S_all      1.040
_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)+(0.0217P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0583
_refine_ls_wR_factor_ref         0.0625
_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), C3(H3), C4(H4)
;
_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
I1 I 0.13118(5) 0.25031(4) 0.52222(2) 0.03394(13) Uani 1 1 d . . . . .
Br1 Br 0.72202(8) 0.38615(5) 0.62331(4) 0.03276(16) Uani 1 1 d . . . . .
Cu1 Cu 0.500000 0.500000 0.500000 0.0230(2) Uani 1 2 d S . P . .
Br5 Br 0.84110(9) 0.10427(6) 0.26746(4) 0.04321(18) Uani 1 1 d . . . . .
N1 N 0.4919(6) 0.2999(4) 0.4354(3) 0.0235(9) Uani 1 1 d . . . . .
C2 C 0.3503(7) 0.1913(5) 0.4427(3) 0.0246(10) Uani 1 1 d . . . . .
C6 C 0.6345(7) 0.2723(5) 0.3841(3) 0.0260(11) Uani 1 1 d . . . . .
H6 H 0.734442 0.347301 0.379443 0.031 Uiso 1 1 calc R U . . .
C5 C 0.6355(8) 0.1337(5) 0.3377(3) 0.0286(11) Uani 1 1 d . . . . .
C3 C 0.3445(7) 0.0506(5) 0.3987(3) 0.0302(12) Uani 1 1 d . . . . .
H3 H 0.244498 -0.023314 0.405321 0.036 Uiso 1 1 calc R U . . .
C4 C 0.4880(8) 0.0209(5) 0.3451(4) 0.0337(13) Uani 1 1 d . . . . .
H4 H 0.486407 -0.072774 0.314369 0.040 Uiso 1 1 calc R U . . .

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
I1 0.0316(2) 0.0358(2) 0.0364(2) -0.00240(15) 0.01180(16) -0.00246(14)
Br1 0.0374(3) 0.0322(3) 0.0279(3) 0.0012(2) 0.0023(2) 0.0046(2)
Cu1 0.0269(4) 0.0194(4) 0.0236(5) -0.0036(3) 0.0064(4) -0.0003(3)
Br5 0.0491(4) 0.0496(4) 0.0344(4) -0.0088(3) 0.0176(3) 0.0082(3)
N1 0.026(2) 0.0211(19) 0.024(2) -0.0022(16) 0.0040(18) 0.0011(16)
C2 0.028(3) 0.023(2) 0.023(3) 0.003(2) 0.003(2) 0.006(2)
C6 0.032(3) 0.023(2) 0.023(3) 0.002(2) 0.003(2) 0.007(2)
C5 0.035(3) 0.030(3) 0.023(3) -0.003(2) 0.010(2) 0.009(2)
C3 0.030(3) 0.023(2) 0.037(3) 0.000(2) 0.001(2) -0.009(2)
C4 0.043(3) 0.025(3) 0.032(3) -0.012(2) 0.004(3) 0.005(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
I1 C2 2.093(5) . ?
Br1 Cu1 2.4266(14) . ?
Cu1 N1 1.977(4) . ?
Cu1 N1 1.977(4) 3_666 ?
Br5 C5 1.877(5) . ?
N1 C2 1.334(6) . ?
N1 C6 1.339(6) . ?
C2 C3 1.379(6) . ?
C6 H6 0.9300 . ?
C6 C5 1.384(6) . ?
C5 C4 1.387(7) . ?
C3 H3 0.9300 . ?
C3 C4 1.371(6) . ?
C4 H4 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
Br1 Cu1 Br1 180.0 3_666 . ?
N1 Cu1 Br1 90.97(12) . . ?
N1 Cu1 Br1 90.97(12) 3_666 3_666 ?
N1 Cu1 Br1 89.03(12) . 3_666 ?
N1 Cu1 Br1 89.03(12) 3_666 . ?
N1 Cu1 N1 180.0(2) . 3_666 ?
C2 N1 Cu1 121.7(3) . . ?
C2 N1 C6 119.4(4) . . ?
C6 N1 Cu1 118.9(3) . . ?
N1 C2 I1 115.8(3) . . ?
N1 C2 C3 122.2(4) . . ?
C3 C2 I1 121.9(3) . . ?
N1 C6 H6 119.5 . . ?
N1 C6 C5 121.0(4) . . ?
C5 C6 H6 119.5 . . ?
C6 C5 Br5 118.2(4) . . ?
C6 C5 C4 119.7(4) . . ?
C4 C5 Br5 122.1(3) . . ?
C2 C3 H3 120.4 . . ?
C4 C3 C2 119.2(4) . . ?
C4 C3 H3 120.4 . . ?
C5 C4 H4 120.8 . . ?
C3 C4 C5 118.5(4) . . ?
C3 C4 H4 120.8 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
I1 C2 C3 C4 177.6(4) . . . . ?
Cu1 N1 C2 I1 2.6(5) . . . . ?
Cu1 N1 C2 C3 -179.3(4) . . . . ?
Cu1 N1 C6 C5 179.8(4) . . . . ?
Br5 C5 C4 C3 179.2(4) . . . . ?
N1 C2 C3 C4 -0.4(8) . . . . ?
N1 C6 C5 Br5 -179.9(4) . . . . ?
N1 C6 C5 C4 -0.6(8) . . . . ?
C2 N1 C6 C5 0.8(7) . . . . ?
C2 C3 C4 C5 0.6(8) . . . . ?
C6 N1 C2 I1 -178.5(3) . . . . ?
C6 N1 C2 C3 -0.3(7) . . . . ?
C6 C5 C4 C3 -0.1(8) . . . . ?

_shelx_res_file                  
;
TITL exp_1248_a.res in P2(1)/n
    exp_1248.res
    created by SHELXL-2018/3 at 01:17:58 on 20-Aug-2022
REM Old TITL exp_1248 in P21/n #14
REM SHELXT solution in P2(1)/n: R1 0.096, Rweak 0.117, Alpha 0.019
REM <I/s> 0.751 for 129 systematic absences, Orientation as input
REM Formula found by SHELXT: C10 N2 Cu Br4 I2
CELL 0.71073 6.5988 8.5468 15.4433 90 98.566 90
ZERR 2 0.0012 0.0007 0.0115 0 0.04 0
LATT 1
SYMM 0.5-X,0.5+Y,0.5-Z
SFAC C H N Cu Br I
UNIT 20 12 4 2 8 4

L.S. 10
PLAN  4
CONF
BOND
list 4
MORE -1
BOND $H
fmap 2
acta
REM <olex2.extras>
REM <HklSrc "%.\\exp_1248.hkl">
REM </olex2.extras>

WGHT    0.021700
EXTI    0.006383
FVAR       0.36459
I1    6    0.131176    0.250306    0.522224    11.00000    0.03164    0.03579 =
         0.03643   -0.00240    0.01180   -0.00246
BR1   5    0.722023    0.386146    0.623309    11.00000    0.03744    0.03217 =
         0.02787    0.00116    0.00226    0.00463
CU1   4    0.500000    0.500000    0.500000    10.50000    0.02686    0.01938 =
         0.02364   -0.00358    0.00636   -0.00030
BR5   5    0.841095    0.104266    0.267459    11.00000    0.04910    0.04958 =
         0.03443   -0.00885    0.01763    0.00819
N1    3    0.491941    0.299932    0.435385    11.00000    0.02563    0.02106 =
         0.02404   -0.00223    0.00404    0.00115
C2    1    0.350325    0.191273    0.442727    11.00000    0.02767    0.02310 =
         0.02301    0.00257    0.00341    0.00620
C6    1    0.634522    0.272284    0.384056    11.00000    0.03181    0.02307 =
         0.02297    0.00248    0.00331    0.00670
AFIX  43
H6    2    0.734442    0.347301    0.379443    11.00000   -1.20000
AFIX   0
C5    1    0.635458    0.133708    0.337744    11.00000    0.03525    0.02962 =
         0.02274   -0.00342    0.01018    0.00950
C3    1    0.344531    0.050563    0.398711    11.00000    0.02992    0.02254 =
         0.03707   -0.00038    0.00128   -0.00857
AFIX  43
H3    2    0.244498   -0.023314    0.405321    11.00000   -1.20000
AFIX   0
C4    1    0.487972    0.020897    0.345105    11.00000    0.04283    0.02513 =
         0.03243   -0.01165    0.00355    0.00481
AFIX  43
H4    2    0.486407   -0.072774    0.314369    11.00000   -1.20000
AFIX   0
HKLF 4




REM  exp_1248_a.res in P2(1)/n
REM wR2 = 0.0625, GooF = S = 1.040, Restrained GooF = 1.040 for all data
REM R1 = 0.0338 for 1627 Fo > 4sig(Fo) and 0.0462 for all 1996 data
REM 89 parameters refined using 0 restraints

END

WGHT      0.0217      0.0000

REM Highest difference peak  0.938,  deepest hole -0.758,  1-sigma level  0.165
Q1    1   0.1355  0.1393  0.5241  11.00000  0.05    0.94
Q2    1   0.1205  0.3594  0.5234  11.00000  0.05    0.92
Q3    1   0.7373  0.4940  0.6238  11.00000  0.05    0.80
Q4    1   0.2414  0.1798  0.5019  11.00000  0.05    0.71
;
_shelx_res_checksum              23220
_olex2_date_sample_data_collection 2014-06-25
_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_exp_1498
_database_code_depnum_ccdc_archive 'CCDC 2224783'
loop_
_audit_author_name
_audit_author_address
Fandi
;The University of Jordan
Jordan
;
_audit_update_record             
;
2022-12-06 deposited with the CCDC.	2023-03-28 downloaded from the CCDC.
;
_audit_creation_date             2022-08-20
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_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          ?
_chemical_oxdiff_formula         'Cu Cl C H I N Br'
_chemical_oxdiff_usercomment     'CuBr2 2i5clpy acn manal hot'
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'
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'

_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/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_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                   6.5931(3)
_cell_length_b                   8.5490(4)
_cell_length_c                   15.1333(9)
_cell_angle_alpha                90
_cell_angle_beta                 98.729(5)
_cell_angle_gamma                90
_cell_volume                     843.10(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1200
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.1005
_cell_measurement_theta_min      3.1196
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    10.000
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.64786
_exptl_absorpt_correction_type   multi-scan
_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_absorpt_special_details   ?
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    2.766
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       parallelepiped
_exptl_crystal_F_000             638
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0317
_diffrn_reflns_av_unetI/netI     0.0501
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.858
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            3694
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.858
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.165
_diffrn_reflns_theta_min         3.215
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.0534
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.858
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -36.00   49.00   1.0000    3.4900
omega____ theta____ kappa____ phi______ frames
    -      -15.2878   77.0000   90.0000 85

#__ type_ start__ end____ width___ exp.time_
  2 omega  -14.00   14.00   1.0000    3.4900
omega____ theta____ kappa____ phi______ frames
    -      -15.2878  -94.0000 -148.0000 28

#__ type_ start__ end____ width___ exp.time_
  3 omega   -2.00   85.00   1.0000    3.4900
omega____ theta____ kappa____ phi______ frames
    -       15.9128   38.0000 -120.0000 87
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0128187000
_diffrn_orient_matrix_UB_12      0.0821644000
_diffrn_orient_matrix_UB_13      -0.0027879000
_diffrn_orient_matrix_UB_21      0.0232800000
_diffrn_orient_matrix_UB_22      -0.0083520000
_diffrn_orient_matrix_UB_23      -0.0439855000
_diffrn_orient_matrix_UB_31      -0.1055710000
_diffrn_orient_matrix_UB_32      0.0081435000
_diffrn_orient_matrix_UB_33      -0.0174279000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1541
_reflns_number_total             1956
_reflns_odcompleteness_completeness 99.78
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_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_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         0.767
_refine_diff_density_min         -0.674
_refine_diff_density_rms         0.158
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     88
_refine_ls_number_reflns         1956
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0510
_refine_ls_R_factor_gt           0.0356
_refine_ls_restrained_S_all      1.024
_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)+(0.0246P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0671
_refine_ls_wR_factor_ref         0.0745
_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
I2 I 0.13017(5) 0.74877(4) 0.52207(3) 0.03751(13) Uani 1 1 d . . . . .
Br1 Br 0.27725(8) 0.38390(6) 0.37531(4) 0.03620(16) Uani 1 1 d . . . . .
Cu1 Cu 0.500000 0.500000 0.500000 0.0261(2) Uani 1 2 d S . P . .
Cl5 Cl 0.8257(2) 0.8965(2) 0.26989(10) 0.0527(4) Uani 1 1 d . . . . .
C5 C 0.6338(8) 0.8671(7) 0.3350(3) 0.0336(13) Uani 1 1 d . . . . .
C3 C 0.3433(8) 0.9483(6) 0.3964(4) 0.0345(13) Uani 1 1 d . . . . .
H3 H 0.241809 1.021161 0.402808 0.041 Uiso 1 1 calc R U . . .
C2 C 0.3499(7) 0.8067(6) 0.4409(3) 0.0281(11) Uani 1 1 d . . . . .
C4 C 0.4885(8) 0.9803(6) 0.3427(4) 0.0371(13) Uani 1 1 d . . . . .
H4 H 0.488641 1.075089 0.312497 0.045 Uiso 1 1 calc R U . . .
N1 N 0.4910(6) 0.6985(5) 0.4336(3) 0.0279(9) Uani 1 1 d . . . . .
C6 C 0.6321(8) 0.7289(6) 0.3804(3) 0.0284(12) Uani 1 1 d . . . . .
H6 H 0.731254 0.653933 0.374257 0.034 Uiso 1 1 calc R U . . .

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 0.0340(2) 0.0373(2) 0.0436(3) 0.00187(17) 0.01362(17) 0.00283(16)
Br1 0.0407(3) 0.0336(3) 0.0334(3) -0.0009(2) 0.0028(2) -0.0048(3)
Cu1 0.0291(4) 0.0207(4) 0.0294(5) 0.0034(4) 0.0072(4) -0.0001(4)
Cl5 0.0588(9) 0.0597(11) 0.0444(9) 0.0107(8) 0.0235(8) -0.0098(8)
C5 0.042(3) 0.039(3) 0.019(3) 0.002(2) 0.005(2) -0.012(3)
C3 0.035(3) 0.023(3) 0.045(3) 0.001(3) 0.001(3) 0.004(2)
C2 0.027(3) 0.027(3) 0.030(3) -0.002(2) 0.003(2) -0.002(2)
C4 0.046(3) 0.027(3) 0.038(3) 0.011(3) 0.003(3) -0.001(3)
N1 0.033(2) 0.025(2) 0.027(2) 0.0028(19) 0.0099(19) -0.002(2)
C6 0.034(3) 0.025(3) 0.027(3) 0.001(2) 0.007(2) -0.003(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
I2 C2 2.096(5) . ?
Br1 Cu1 2.4210(5) . ?
Cu1 N1 1.968(4) . ?
Cu1 N1 1.968(4) 3_666 ?
Cl5 C5 1.735(5) . ?
C5 C4 1.379(7) . ?
C5 C6 1.368(7) . ?
C3 H3 0.9300 . ?
C3 C2 1.383(7) . ?
C3 C4 1.374(7) . ?
C2 N1 1.329(6) . ?
C4 H4 0.9300 . ?
N1 C6 1.345(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
Br1 Cu1 Br1 180.00(2) 3_666 . ?
N1 Cu1 Br1 89.29(13) 3_666 3_666 ?
N1 Cu1 Br1 90.71(13) 3_666 . ?
N1 Cu1 Br1 89.29(13) . . ?
N1 Cu1 Br1 90.71(13) . 3_666 ?
N1 Cu1 N1 180.0 3_666 . ?
C4 C5 Cl5 121.5(4) . . ?
C6 C5 Cl5 118.2(4) . . ?
C6 C5 C4 120.3(5) . . ?
C2 C3 H3 120.3 . . ?
C4 C3 H3 120.3 . . ?
C4 C3 C2 119.3(5) . . ?
C3 C2 I2 121.3(4) . . ?
N1 C2 I2 116.1(4) . . ?
N1 C2 C3 122.7(5) . . ?
C5 C4 H4 121.1 . . ?
C3 C4 C5 117.7(5) . . ?
C3 C4 H4 121.1 . . ?
C2 N1 Cu1 121.7(3) . . ?
C2 N1 C6 118.2(4) . . ?
C6 N1 Cu1 120.2(3) . . ?
C5 C6 H6 119.1 . . ?
N1 C6 C5 121.8(5) . . ?
N1 C6 H6 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
I2 C2 N1 Cu1 -2.9(5) . . . . ?
I2 C2 N1 C6 178.4(4) . . . . ?
Cu1 N1 C6 C5 -178.3(4) . . . . ?
Cl5 C5 C4 C3 -179.2(4) . . . . ?
Cl5 C5 C6 N1 178.7(4) . . . . ?
C3 C2 N1 Cu1 178.5(4) . . . . ?
C3 C2 N1 C6 -0.2(8) . . . . ?
C2 C3 C4 C5 0.7(8) . . . . ?
C2 N1 C6 C5 0.4(8) . . . . ?
C4 C5 C6 N1 -0.1(8) . . . . ?
C4 C3 C2 I2 -178.9(4) . . . . ?
C4 C3 C2 N1 -0.4(8) . . . . ?
C6 C5 C4 C3 -0.5(8) . . . . ?

_shelx_res_file                  
;
TITL exp_1498 in P21/n #14
    exp_1498.res
    created by SHELXL-2018/3 at 01:31:46 on 20-Aug-2022
REM reset to P21/n #14
CELL 0.71073 6.593121 8.549007 15.133319 90 98.7288 90
ZERR 2 0.00032 0.000411 0.000897 0 0.0051 0
LATT 1
SYMM 0.5-X,0.5+Y,0.5-Z
SFAC C H N Cl Cu Br I
UNIT 20 12 4 4 2 4 4

L.S. 8 0 0
PLAN  4
CONF
BOND
MORE -1
BOND $H
fmap 2
acta
REM <olex2.extras>
REM <HklSrc "%.\\exp_1498.hkl">
REM </olex2.extras>

WGHT    0.024600
FVAR       3.54098
I2    7    0.130170    0.748775    0.522070    11.00000    0.03400    0.03732 =
         0.04362    0.00187    0.01362    0.00283
BR1   6    0.277254    0.383904    0.375309    11.00000    0.04068    0.03364 =
         0.03342   -0.00094    0.00281   -0.00476
CU1   5    0.500000    0.500000    0.500000    10.50000    0.02913    0.02075 =
         0.02939    0.00343    0.00724   -0.00009
CL5   4    0.825729    0.896471    0.269885    11.00000    0.05880    0.05971 =
         0.04439    0.01066    0.02350   -0.00979
C5    1    0.633824    0.867141    0.334956    11.00000    0.04199    0.03928 =
         0.01939    0.00204    0.00461   -0.01246
C3    1    0.343349    0.948329    0.396411    11.00000    0.03468    0.02288 =
         0.04450    0.00126    0.00091    0.00356
AFIX  43
H3    2    0.241809    1.021161    0.402808    11.00000   -1.20000
AFIX   0
C2    1    0.349871    0.806720    0.440889    11.00000    0.02681    0.02696 =
         0.03012   -0.00170    0.00334   -0.00194
C4    1    0.488453    0.980324    0.342661    11.00000    0.04551    0.02717 =
         0.03763    0.01110    0.00301   -0.00076
AFIX  43
H4    2    0.488641    1.075089    0.312497    11.00000   -1.20000
AFIX   0
N1    3    0.491016    0.698469    0.433569    11.00000    0.03280    0.02518 =
         0.02729    0.00280    0.00986   -0.00246
C6    1    0.632127    0.728920    0.380351    11.00000    0.03375    0.02517 =
         0.02702    0.00059    0.00720   -0.00298
AFIX  43
H6    2    0.731254    0.653933    0.374257    11.00000   -1.20000
AFIX   0
HKLF 4




REM  exp_1498 in P21/n #14
REM wR2 = 0.0745, GooF = S = 1.024, Restrained GooF = 1.024 for all data
REM R1 = 0.0356 for 1541 Fo > 4sig(Fo) and 0.0510 for all 1956 data
REM 88 parameters refined using 0 restraints

END

WGHT      0.0246      0.0000

REM Highest difference peak  0.767,  deepest hole -0.674,  1-sigma level  0.158
Q1    1   0.1322  0.8733  0.5240  11.00000  0.05    0.77
Q2    1   0.4873  0.3783  0.5041  11.00000  0.05    0.76
Q3    1   0.3742  0.5156  0.4599  11.00000  0.05    0.71
Q4    1   0.3773  0.3985  0.4250  11.00000  0.05    0.61
;
_shelx_res_checksum              59180
_olex2_date_sample_data_collection 2014-12-16
_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_exp_1502
_database_code_depnum_ccdc_archive 'CCDC 2224785'
loop_
_audit_author_name
_audit_author_address
Fandi
;The University of Jordan
Jordan
;
_audit_update_record             
;
2022-12-06 deposited with the CCDC.	2023-03-28 downloaded from the CCDC.
;
_audit_creation_date             2022-08-19
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_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          ?
_chemical_oxdiff_formula         'Cu Cl Br C H N'
_chemical_oxdiff_usercomment     '2c5bp cucl2 1:1 dr firas acn hot'
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'
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'

_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/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_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                   10.8035(8)
_cell_length_b                   14.9629(5)
_cell_length_c                   6.6080(5)
_cell_angle_alpha                90
_cell_angle_beta                 128.800(11)
_cell_angle_gamma                90
_cell_volume                     832.48(14)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1654
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.1460
_cell_measurement_theta_min      4.1000
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    10.127
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70189
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    2.801
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       fragment
_exptl_crystal_F_000             638
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0330
_diffrn_reflns_av_unetI/netI     0.0535
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.847
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            3956
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.847
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.295
_diffrn_reflns_theta_min         3.083
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0534
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.847
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -37.00  50.00   1.00    6.00    --  -15.13  77.00 -90.00   87
  2  ω     -4.00  82.00   1.00    6.00    --   15.76  77.00  30.00   86
  3  ω     40.00  73.00   1.00    6.00    --   15.76  77.00 150.00   33
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0271053000
_diffrn_orient_matrix_UB_12      -0.0442595000
_diffrn_orient_matrix_UB_13      -0.0106696000
_diffrn_orient_matrix_UB_21      -0.0192865000
_diffrn_orient_matrix_UB_22      0.0113726000
_diffrn_orient_matrix_UB_23      0.0815323000
_diffrn_orient_matrix_UB_31      -0.0773623000
_diffrn_orient_matrix_UB_32      0.0126485000
_diffrn_orient_matrix_UB_33      -0.1104470000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1501
_reflns_number_total             1933
_reflns_odcompleteness_completeness 99.78
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.629
_refine_diff_density_min         -1.061
_refine_diff_density_rms         0.185
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     88
_refine_ls_number_reflns         1933
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0559
_refine_ls_R_factor_gt           0.0384
_refine_ls_restrained_S_all      1.046
_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)+(0.0278P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0721
_refine_ls_wR_factor_ref         0.0821
_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
I2 I 0.74809(5) 0.51859(3) -0.13384(8) 0.03855(15) Uani 1 1 d . . . . .
Cu1 Cu 0.500000 0.500000 0.000000 0.0259(2) Uani 1 2 d S . P . .
Br5 Br 0.91030(8) 0.26254(4) 0.83289(13) 0.0453(2) Uani 1 1 d . . . . .
Cl1 Cl 0.61867(17) 0.61457(10) 0.2847(3) 0.0389(4) Uani 1 1 d . . . . .
N1 N 0.7027(5) 0.4309(3) 0.2117(8) 0.0258(10) Uani 1 1 d . . . . .
C2 C 0.8103(6) 0.4386(4) 0.1783(11) 0.0286(12) Uani 1 1 d . . . . .
C6 C 0.7346(6) 0.3776(4) 0.4041(10) 0.0297(13) Uani 1 1 d . . . . .
H6 H 0.659222 0.371445 0.428725 0.036 Uiso 1 1 calc R U . . .
C4 C 0.9887(6) 0.3409(4) 0.5299(11) 0.0356(14) Uani 1 1 d . . . . .
H4 H 1.085098 0.310703 0.636445 0.043 Uiso 1 1 calc R U . . .
C5 C 0.8767(6) 0.3322(4) 0.5651(10) 0.0311(13) Uani 1 1 d . . . . .
C3 C 0.9546(7) 0.3953(4) 0.3330(11) 0.0371(14) Uani 1 1 d . . . . .
H3 H 1.028117 0.402820 0.304681 0.045 Uiso 1 1 calc R U . . .

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 0.0374(3) 0.0459(3) 0.0362(3) 0.00740(18) 0.0249(2) 0.00340(18)
Cu1 0.0209(5) 0.0297(5) 0.0238(5) 0.0011(4) 0.0123(4) 0.0030(4)
Br5 0.0519(4) 0.0396(4) 0.0399(4) 0.0127(3) 0.0265(4) 0.0093(3)
Cl1 0.0322(8) 0.0394(8) 0.0357(9) -0.0085(6) 0.0167(7) -0.0007(7)
N1 0.019(2) 0.031(3) 0.018(2) 0.0019(19) 0.007(2) 0.0021(19)
C2 0.025(3) 0.032(3) 0.028(3) 0.001(2) 0.017(3) 0.001(2)
C6 0.028(3) 0.034(3) 0.022(3) 0.000(2) 0.013(3) 0.000(3)
C4 0.026(3) 0.036(3) 0.035(4) 0.004(3) 0.015(3) 0.010(3)
C5 0.033(3) 0.027(3) 0.027(3) -0.001(2) 0.016(3) -0.001(2)
C3 0.027(3) 0.049(4) 0.034(4) 0.004(3) 0.019(3) 0.009(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 2.098(5) . ?
Cu1 Cl1 2.2581(14) 3_665 ?
Cu1 Cl1 2.2581(14) . ?
Cu1 N1 1.996(4) 3_665 ?
Cu1 N1 1.996(4) . ?
Br5 C5 1.883(5) . ?
N1 C2 1.317(6) . ?
N1 C6 1.349(7) . ?
C2 C3 1.378(7) . ?
C6 H6 0.9300 . ?
C6 C5 1.380(7) . ?
C4 H4 0.9300 . ?
C4 C5 1.374(7) . ?
C4 C3 1.375(8) . ?
C3 H3 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
Cl1 Cu1 Cl1 180.0 3_665 . ?
N1 Cu1 Cl1 89.50(13) 3_665 . ?
N1 Cu1 Cl1 89.50(13) . 3_665 ?
N1 Cu1 Cl1 90.50(13) 3_665 3_665 ?
N1 Cu1 Cl1 90.50(13) . . ?
N1 Cu1 N1 180.0 3_665 . ?
C2 N1 Cu1 122.2(4) . . ?
C2 N1 C6 118.6(5) . . ?
C6 N1 Cu1 119.1(4) . . ?
N1 C2 I2 116.2(4) . . ?
N1 C2 C3 122.8(5) . . ?
C3 C2 I2 120.9(4) . . ?
N1 C6 H6 119.3 . . ?
N1 C6 C5 121.4(5) . . ?
C5 C6 H6 119.3 . . ?
C5 C4 H4 120.9 . . ?
C5 C4 C3 118.3(5) . . ?
C3 C4 H4 120.9 . . ?
C6 C5 Br5 117.6(4) . . ?
C4 C5 Br5 122.7(4) . . ?
C4 C5 C6 119.7(5) . . ?
C2 C3 H3 120.4 . . ?
C4 C3 C2 119.2(5) . . ?
C4 C3 H3 120.4 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
I2 C2 C3 C4 -177.7(4) . . . . ?
Cu1 N1 C2 I2 -5.5(6) . . . . ?
Cu1 N1 C2 C3 176.1(4) . . . . ?
Cu1 N1 C6 C5 -176.5(4) . . . . ?
N1 C2 C3 C4 0.7(9) . . . . ?
N1 C6 C5 Br5 178.3(4) . . . . ?
N1 C6 C5 C4 -0.1(9) . . . . ?
C2 N1 C6 C5 0.4(8) . . . . ?
C6 N1 C2 I2 177.7(4) . . . . ?
C6 N1 C2 C3 -0.7(8) . . . . ?
C5 C4 C3 C2 -0.3(9) . . . . ?
C3 C4 C5 Br5 -178.2(4) . . . . ?
C3 C4 C5 C6 0.1(9) . . . . ?

_shelx_res_file                  
;
TITL exp_1502_a.res in P2(1)/n
    exp_1502.res
    created by SHELXL-2018/3 at 23:50:36 on 18-Aug-2022
REM Old TITL exp_1502 in P2(1)/n
REM SHELXT solution in P2(1)/n: R1 0.174, Rweak 0.148, Alpha 0.020
REM <I/s> 0.669 for 76 systematic absences, Orientation as input
REM Formula found by SHELXT: C10 N2 Cl2 Cu Br4
CELL 0.71073 10.8035 14.9629 6.608 90 128.8 90
ZERR 2 0.0008 0.0005 0.0005 0 0.011 0
LATT 1
SYMM 0.5-X,0.5+Y,0.5-Z
SFAC C H N Cl Cu Br I
UNIT 20 12 4 4 2 4 4

L.S. 4 0 0
PLAN  4
CONF
BOND
list 4
MORE -1
BOND $H
fmap 2 53
acta
REM <olex2.extras>
REM <HklSrc "%.\\exp_1502.hkl">
REM </olex2.extras>

WGHT    0.027800
FVAR       0.43632
I2    7    0.748092    0.518592   -0.133835    11.00000    0.03743    0.04589 =
         0.03620    0.00740    0.02494    0.00340
CU1   5    0.500000    0.500000    0.000000    10.50000    0.02094    0.02966 =
         0.02379    0.00113    0.01235    0.00299
BR5   6    0.910301    0.262540    0.832886    11.00000    0.05190    0.03960 =
         0.03988    0.01268    0.02649    0.00934
CL1   4    0.618671    0.614573    0.284696    11.00000    0.03218    0.03941 =
         0.03574   -0.00853    0.01667   -0.00075
N1    3    0.702697    0.430885    0.211667    11.00000    0.01855    0.03069 =
         0.01849    0.00189    0.00686    0.00210
C2    1    0.810254    0.438564    0.178257    11.00000    0.02545    0.03226 =
         0.02796    0.00115    0.01673    0.00125
C6    1    0.734623    0.377646    0.404086    11.00000    0.02806    0.03428 =
         0.02200   -0.00021    0.01344    0.00012
AFIX  43
H6    2    0.659222    0.371445    0.428725    11.00000   -1.20000
AFIX   0
C4    1    0.988719    0.340869    0.529890    11.00000    0.02559    0.03640 =
         0.03531    0.00395    0.01453    0.01010
AFIX  43
H4    2    1.085098    0.310703    0.636445    11.00000   -1.20000
AFIX   0
C5    1    0.876718    0.332202    0.565100    11.00000    0.03299    0.02699 =
         0.02738   -0.00073    0.01596   -0.00124
C3    1    0.954609    0.395297    0.333033    11.00000    0.02741    0.04943 =
         0.03393    0.00396    0.01894    0.00852
AFIX  43
H3    2    1.028117    0.402820    0.304681    11.00000   -1.20000
AFIX   0
HKLF 4




REM  exp_1502_a.res in P2(1)/n
REM wR2 = 0.0821, GooF = S = 1.046, Restrained GooF = 1.046 for all data
REM R1 = 0.0384 for 1501 Fo > 4sig(Fo) and 0.0559 for all 1933 data
REM 88 parameters refined using 0 restraints

END

WGHT      0.0278      0.0000

REM Highest difference peak  0.629,  deepest hole -1.061,  1-sigma level  0.185
Q1    1   0.7404  0.1977  0.7179  11.00000  0.05    0.63
Q2    1   0.5783  0.4640 -0.1784  11.00000  0.05    0.62
Q3    1   0.5782  0.3664  0.0410  11.00000  0.05    0.59
Q4    1   1.1370  0.3211  0.7952  11.00000  0.05    0.57
;
_shelx_res_checksum              30741
_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 1.339
_oxdiff_exptl_absorpt_empirical_full_min 0.800
####################################################################### 
# 
# 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_1493
_database_code_depnum_ccdc_archive 'CCDC 2224782'
loop_
_audit_author_name
_audit_author_address
Fandi
;The University of Jordan
Jordan
;
_audit_update_record             
;
2022-12-06 deposited with the CCDC.	2023-03-28 downloaded from the CCDC.
;
_audit_creation_date             2022-08-20
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_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          ?
_chemical_oxdiff_formula         'Cu Cl C H I N'
_chemical_oxdiff_usercomment     'Cucl2 2i5clpy acn manal hot'
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'

_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/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_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                   6.5889(19)
_cell_length_b                   8.4455(10)
_cell_length_c                   14.910(7)
_cell_angle_alpha                90
_cell_angle_beta                 99.21(4)
_cell_angle_gamma                90
_cell_volume                     819.0(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1269
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.3265
_cell_measurement_theta_min      3.1299
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    5.741
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80937
_exptl_absorpt_correction_type   multi-scan
_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_absorpt_special_details   ?
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    2.487
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       parallelepiped
_exptl_crystal_F_000             566
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0269
_diffrn_reflns_av_unetI/netI     0.0448
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.855
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            4062
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.855
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.387
_diffrn_reflns_theta_min         3.215
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.0534
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.855
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   -3.00   85.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       15.9128   38.0000    0.0000 88

#__ type_ start__ end____ width___ exp.time_
  2 omega  -34.00   58.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       15.9128    0.0000  150.0000 92

#__ type_ start__ end____ width___ exp.time_
  3 omega    5.00   43.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       15.9128  -77.0000 -150.0000 38
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0460436000
_diffrn_orient_matrix_UB_12      -0.0188419000
_diffrn_orient_matrix_UB_13      0.0450287000
_diffrn_orient_matrix_UB_21      0.0955576000
_diffrn_orient_matrix_UB_22      -0.0128301000
_diffrn_orient_matrix_UB_23      -0.0150253000
_diffrn_orient_matrix_UB_31      0.0259247000
_diffrn_orient_matrix_UB_32      0.0807252000
_diffrn_orient_matrix_UB_33      0.0081691000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1493
_reflns_number_total             1930
_reflns_odcompleteness_completeness 99.78
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_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_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.761
_refine_diff_density_min         -0.532
_refine_diff_density_rms         0.123
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     88
_refine_ls_number_reflns         1930
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0489
_refine_ls_R_factor_gt           0.0324
_refine_ls_restrained_S_all      1.035
_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)+(0.0191P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0557
_refine_ls_wR_factor_ref         0.0652
_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), C3(H3), C4(H4)
;
_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
I2 I 0.87841(4) 0.25189(3) 0.47928(2) 0.04048(12) Uani 1 1 d . . . . .
Cu1 Cu 0.500000 0.500000 0.500000 0.02786(18) Uani 1 2 d S . P . .
Cl1 Cl 0.70937(17) 0.61547(11) 0.61684(8) 0.0411(3) Uani 1 1 d . . . . .
Cl5 Cl 0.1868(2) 0.09423(14) 0.73357(9) 0.0556(4) Uani 1 1 d . . . . .
N1 N 0.5186(5) 0.2985(3) 0.5688(3) 0.0289(8) Uani 1 1 d . . . . .
C2 C 0.6623(6) 0.1894(4) 0.5615(3) 0.0312(10) Uani 1 1 d . . . . .
C6 C 0.3781(7) 0.2666(4) 0.6226(3) 0.0315(10) Uani 1 1 d . . . . .
H6 H 0.278109 0.341795 0.628711 0.038 Uiso 1 1 calc R U . . .
C3 C 0.6688(6) 0.0467(4) 0.6065(3) 0.0393(12) Uani 1 1 d . . . . .
H3 H 0.770224 -0.026947 0.599784 0.047 Uiso 1 1 calc R U . . .
C5 C 0.3783(6) 0.1260(5) 0.6687(3) 0.0342(10) Uani 1 1 d . . . . .
C4 C 0.5269(7) 0.0131(5) 0.6608(3) 0.0413(12) Uani 1 1 d . . . . .
H4 H 0.529650 -0.082767 0.691636 0.050 Uiso 1 1 calc R U . . .

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 0.03895(19) 0.0398(2) 0.0458(2) 0.00260(15) 0.01624(16) 0.00441(12)
Cu1 0.0334(4) 0.0221(3) 0.0294(5) 0.0029(3) 0.0089(3) 0.0005(3)
Cl1 0.0488(7) 0.0347(6) 0.0380(7) -0.0014(5) 0.0017(6) -0.0044(5)
Cl5 0.0661(9) 0.0617(8) 0.0445(9) 0.0090(7) 0.0258(7) -0.0113(6)
N1 0.0323(19) 0.0231(15) 0.031(2) -0.0004(16) 0.0040(17) -0.0007(14)
C2 0.033(2) 0.0256(19) 0.035(3) -0.001(2) 0.004(2) 0.0009(17)
C6 0.036(2) 0.029(2) 0.029(3) -0.0032(19) 0.005(2) -0.0007(17)
C3 0.044(3) 0.024(2) 0.049(4) 0.001(2) 0.005(2) 0.0022(18)
C5 0.040(2) 0.037(2) 0.027(3) 0.001(2) 0.006(2) -0.0103(19)
C4 0.052(3) 0.027(2) 0.043(3) 0.014(2) 0.002(2) -0.001(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
I2 C2 2.090(4) . ?
Cu1 Cl1 2.2626(14) 3_666 ?
Cu1 Cl1 2.2626(14) . ?
Cu1 N1 1.980(3) . ?
Cu1 N1 1.980(3) 3_666 ?
Cl5 C5 1.729(4) . ?
N1 C2 1.339(5) . ?
N1 C6 1.346(5) . ?
C2 C3 1.377(5) . ?
C6 H6 0.9300 . ?
C6 C5 1.371(5) . ?
C3 H3 0.9300 . ?
C3 C4 1.360(6) . ?
C5 C4 1.386(6) . ?
C4 H4 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 89.54(11) . . ?
N1 Cu1 Cl1 89.54(11) 3_666 3_666 ?
N1 Cu1 Cl1 90.46(11) . 3_666 ?
N1 Cu1 Cl1 90.46(11) 3_666 . ?
N1 Cu1 N1 180.00(18) . 3_666 ?
C2 N1 Cu1 122.4(3) . . ?
C2 N1 C6 118.2(3) . . ?
C6 N1 Cu1 119.3(3) . . ?
N1 C2 I2 115.5(3) . . ?
N1 C2 C3 122.1(4) . . ?
C3 C2 I2 122.4(3) . . ?
N1 C6 H6 119.1 . . ?
N1 C6 C5 121.8(4) . . ?
C5 C6 H6 119.1 . . ?
C2 C3 H3 119.9 . . ?
C4 C3 C2 120.1(4) . . ?
C4 C3 H3 119.9 . . ?
C6 C5 Cl5 118.2(3) . . ?
C6 C5 C4 119.8(4) . . ?
C4 C5 Cl5 122.0(3) . . ?
C3 C4 C5 118.0(4) . . ?
C3 C4 H4 121.0 . . ?
C5 C4 H4 121.0 . . ?

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
I2 C2 C3 C4 178.6(4) . . . . ?
Cu1 N1 C2 I2 3.9(5) . . . . ?
Cu1 N1 C2 C3 -177.1(3) . . . . ?
Cu1 N1 C6 C5 177.1(3) . . . . ?
Cl5 C5 C4 C3 178.4(4) . . . . ?
N1 C2 C3 C4 -0.4(7) . . . . ?
N1 C6 C5 Cl5 -178.2(3) . . . . ?
N1 C6 C5 C4 0.4(7) . . . . ?
C2 N1 C6 C5 -0.6(7) . . . . ?
C2 C3 C4 C5 0.1(7) . . . . ?
C6 N1 C2 I2 -178.4(3) . . . . ?
C6 N1 C2 C3 0.6(7) . . . . ?
C6 C5 C4 C3 -0.1(7) . . . . ?

_shelx_res_file                  
;
TITL exp_1493_a.res in P2(1)/n
    exp_1493.res
    created by SHELXL-2018/3 at 01:22:35 on 20-Aug-2022
REM Old TITL exp_1493 in P21/n #14
REM SHELXT solution in P2(1)/n: R1 0.100, Rweak 0.160, Alpha 0.017
REM <I/s> 0.574 for 124 systematic absences, Orientation as input
REM Formula found by SHELXT: C10 N2 Cl4 Cu I2
CELL 0.71073 6.5889 8.4455 14.91 90 99.212 90
ZERR 2 0.0019 0.001 0.0065 0 0.038 0
LATT 1
SYMM 0.5-X,0.5+Y,0.5-Z
SFAC C H N Cl Cu I
UNIT 20 12 4 8 2 4

L.S. 4 0 0
PLAN  4
CONF
BOND
list 4
MORE -1
BOND $H
fmap 2
acta
REM <olex2.extras>
REM <HklSrc "%.\\exp_1493.hkl">
REM </olex2.extras>

WGHT    0.019100
FVAR       0.41925
I2    6    0.878414    0.251894    0.479276    11.00000    0.03895    0.03979 =
         0.04581    0.00260    0.01624    0.00441
CU1   5    0.500000    0.500000    0.500000    10.50000    0.03343    0.02205 =
         0.02938    0.00294    0.00893    0.00050
CL1   4    0.709373    0.615471    0.616840    11.00000    0.04879    0.03471 =
         0.03804   -0.00145    0.00171   -0.00439
CL5   4    0.186816    0.094228    0.733567    11.00000    0.06610    0.06172 =
         0.04450    0.00897    0.02580   -0.01132
N1    3    0.518592    0.298531    0.568795    11.00000    0.03234    0.02311 =
         0.03093   -0.00045    0.00399   -0.00073
C2    1    0.662346    0.189363    0.561550    11.00000    0.03298    0.02561 =
         0.03464   -0.00082    0.00417    0.00093
C6    1    0.378056    0.266550    0.622621    11.00000    0.03637    0.02917 =
         0.02887   -0.00321    0.00470   -0.00072
AFIX  43
H6    2    0.278109    0.341795    0.628711    11.00000   -1.20000
AFIX   0
C3    1    0.668757    0.046652    0.606516    11.00000    0.04415    0.02366 =
         0.04920    0.00054    0.00461    0.00224
AFIX  43
H3    2    0.770224   -0.026947    0.599784    11.00000   -1.20000
AFIX   0
C5    1    0.378298    0.126036    0.668707    11.00000    0.03972    0.03664 =
         0.02677    0.00149    0.00650   -0.01034
C4    1    0.526935    0.013102    0.660779    11.00000    0.05222    0.02721 =
         0.04251    0.01414    0.00181   -0.00074
AFIX  43
H4    2    0.529650   -0.082767    0.691636    11.00000   -1.20000
AFIX   0
HKLF 4




REM  exp_1493_a.res in P2(1)/n
REM wR2 = 0.0652, GooF = S = 1.035, Restrained GooF = 1.035 for all data
REM R1 = 0.0324 for 1493 Fo > 4sig(Fo) and 0.0489 for all 1930 data
REM 88 parameters refined using 0 restraints

END

WGHT      0.0191      0.0000

REM Highest difference peak  0.761,  deepest hole -0.532,  1-sigma level  0.123
Q1    1   0.5000  0.0000  0.5000  10.50000  0.05    0.76
Q2    1   0.7905  0.3484  0.4588  11.00000  0.05    0.56
Q3    1   0.8572  0.1400  0.4711  11.00000  0.05    0.55
Q4    1   0.8816  0.3765  0.4773  11.00000  0.05    0.52
;
_shelx_res_checksum              22025
_olex2_date_sample_data_collection 2014-12-16
_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_exp_1504
_database_code_depnum_ccdc_archive 'CCDC 2224784'
loop_
_audit_author_name
_audit_author_address
Fandi
;The University of Jordan
Jordan
;
_audit_update_record             
;
2022-12-06 deposited with the CCDC.	2023-03-28 downloaded from the CCDC.
;
_audit_creation_date             2022-08-20
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_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          ?
_chemical_oxdiff_formula         'Cu Cl Br C H N'
_chemical_oxdiff_usercomment     '2i5bp cucl2 1:1 dr firas acn hot green color'
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'
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'

_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                   8.4631(4)
_cell_length_b                   13.1568(6)
_cell_length_c                   14.6722(5)
_cell_angle_alpha                90
_cell_angle_beta                 91.403(4)
_cell_angle_gamma                90
_cell_volume                     1633.22(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1268
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.4005
_cell_measurement_theta_min      3.1496
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    10.324
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.44727
_exptl_absorpt_correction_type   multi-scan
_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_absorpt_special_details   ?
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    2.856
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       fragment
_exptl_crystal_F_000             1276
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0254
_diffrn_reflns_av_unetI/netI     0.0453
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.859
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            3653
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.859
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.147
_diffrn_reflns_theta_min         3.156
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.0534
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.859
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -33.00   54.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -15.2878   38.0000  -90.0000 87

#__ type_ start__ end____ width___ exp.time_
  2 omega  -83.00  -29.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -15.2878  -38.0000   90.0000 54

#__ type_ start__ end____ width___ exp.time_
  3 omega  -83.00  -53.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -15.2878  -77.0000 -180.0000 30

#__ type_ start__ end____ width___ exp.time_
  4 omega  -41.00  -15.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       15.9128  -62.0000   -7.0000 26
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0779333000
_diffrn_orient_matrix_UB_12      0.0026209000
_diffrn_orient_matrix_UB_13      0.0165461000
_diffrn_orient_matrix_UB_21      0.0238604000
_diffrn_orient_matrix_UB_22      0.0390612000
_diffrn_orient_matrix_UB_23      0.0306953000
_diffrn_orient_matrix_UB_31      -0.0196186000
_diffrn_orient_matrix_UB_32      0.0370530000
_diffrn_orient_matrix_UB_33      -0.0335176000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1545
_reflns_number_total             1901
_reflns_odcompleteness_completeness 99.71
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_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_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         0.499
_refine_diff_density_min         -0.862
_refine_diff_density_rms         0.148
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     87
_refine_ls_number_reflns         1901
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0454
_refine_ls_R_factor_gt           0.0324
_refine_ls_restrained_S_all      1.013
_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)+(0.0202P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0576
_refine_ls_wR_factor_ref         0.0639
_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:
 C4(H4), C6(H6), C3(H3)
;
_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
I2 I 0.15500(4) 0.43058(2) 0.15198(2) 0.03934(12) Uani 1 1 d . . . . .
Br5 Br -0.15909(7) 0.05751(4) -0.10114(3) 0.04128(16) Uani 1 1 d . . . . .
Cu1 Cu 0.000000 0.21384(6) 0.250000 0.02405(19) Uani 1 2 d S T P . .
Cl1 Cl 0.24686(13) 0.15221(10) 0.24091(7) 0.0344(3) Uani 1 1 d . . . . .
C4 C -0.0030(6) 0.2465(4) -0.0756(3) 0.0340(12) Uani 1 1 d . . . . .
H4 H -0.000134 0.249501 -0.138895 0.041 Uiso 1 1 calc R U . . .
C2 C 0.0565(5) 0.3147(3) 0.0715(3) 0.0255(10) Uani 1 1 d . . . . .
C6 C -0.0769(5) 0.1644(3) 0.0617(3) 0.0261(10) Uani 1 1 d . . . . .
H6 H -0.126367 0.110113 0.089827 0.031 Uiso 1 1 calc R U . . .
C3 C 0.0638(6) 0.3229(4) -0.0218(3) 0.0362(12) Uani 1 1 d . . . . .
H3 H 0.112587 0.378516 -0.048295 0.043 Uiso 1 1 calc R U . . .
C5 C -0.0733(5) 0.1664(3) -0.0323(3) 0.0273(10) Uani 1 1 d . . . . .
N1 N -0.0126(4) 0.2369(3) 0.1139(2) 0.0233(8) 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 0.0488(2) 0.0382(2) 0.03123(19) -0.00433(14) 0.00586(15) -0.01516(16)
Br5 0.0489(3) 0.0451(3) 0.0297(3) -0.0099(2) -0.0031(2) -0.0090(3)
Cu1 0.0289(4) 0.0274(4) 0.0159(4) 0.000 0.0027(3) 0.000
Cl1 0.0325(7) 0.0449(7) 0.0261(6) 0.0031(5) 0.0054(5) 0.0063(5)
C4 0.047(3) 0.041(3) 0.014(2) 0.003(2) 0.001(2) -0.002(3)
C2 0.030(3) 0.022(2) 0.025(2) -0.0004(19) 0.0025(19) -0.001(2)
C6 0.028(3) 0.028(2) 0.022(2) 0.004(2) 0.0015(18) -0.007(2)
C3 0.046(3) 0.037(3) 0.026(2) 0.009(2) 0.004(2) -0.010(2)
C5 0.027(2) 0.034(3) 0.020(2) -0.006(2) -0.0011(18) 0.001(2)
N1 0.028(2) 0.0234(19) 0.0189(18) 0.0003(16) 0.0015(14) -0.0005(17)

_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 2.089(4) . ?
Br5 C5 1.888(4) . ?
Cu1 Cl1 2.2481(12) . ?
Cu1 Cl1 2.2481(12) 2 ?
Cu1 N1 2.020(3) 2 ?
Cu1 N1 2.020(3) . ?
C4 H4 0.9300 . ?
C4 C3 1.390(6) . ?
C4 C5 1.375(6) . ?
C2 C3 1.376(6) . ?
C2 N1 1.340(5) . ?
C6 H6 0.9300 . ?
C6 C5 1.381(5) . ?
C6 N1 1.331(5) . ?
C3 H3 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
Cl1 Cu1 Cl1 137.71(8) 2 . ?
N1 Cu1 Cl1 91.26(11) 2 2 ?
N1 Cu1 Cl1 94.95(11) 2 . ?
N1 Cu1 Cl1 91.26(11) . . ?
N1 Cu1 Cl1 94.95(11) . 2 ?
N1 Cu1 N1 162.7(2) 2 . ?
C3 C4 H4 121.1 . . ?
C5 C4 H4 121.1 . . ?
C5 C4 C3 117.8(4) . . ?
C3 C2 I2 118.5(3) . . ?
N1 C2 I2 117.9(3) . . ?
N1 C2 C3 123.6(4) . . ?
C5 C6 H6 118.5 . . ?
N1 C6 H6 118.5 . . ?
N1 C6 C5 122.9(4) . . ?
C4 C3 H3 120.6 . . ?
C2 C3 C4 118.8(4) . . ?
C2 C3 H3 120.6 . . ?
C4 C5 Br5 120.0(3) . . ?
C4 C5 C6 119.8(4) . . ?
C6 C5 Br5 120.2(3) . . ?
C2 N1 Cu1 124.1(3) . . ?
C6 N1 Cu1 118.2(3) . . ?
C6 N1 C2 117.2(4) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
I2 C2 C3 C4 -179.4(4) . . . . ?
I2 C2 N1 Cu1 -9.3(5) . . . . ?
I2 C2 N1 C6 179.0(3) . . . . ?
C3 C4 C5 Br5 -177.6(4) . . . . ?
C3 C4 C5 C6 0.5(7) . . . . ?
C3 C2 N1 Cu1 171.6(4) . . . . ?
C3 C2 N1 C6 0.0(7) . . . . ?
C5 C4 C3 C2 0.0(7) . . . . ?
C5 C6 N1 Cu1 -171.5(3) . . . . ?
C5 C6 N1 C2 0.7(7) . . . . ?
N1 C2 C3 C4 -0.3(7) . . . . ?
N1 C6 C5 Br5 177.2(3) . . . . ?
N1 C6 C5 C4 -0.9(7) . . . . ?

_shelx_res_file                  
;
TITL exp_1504 in C2/c #15
    exp_1504.res
    created by SHELXL-2018/3 at 01:36:21 on 20-Aug-2022
REM reset to C2/c #15
CELL 0.71073 8.463066 13.156832 14.672221 90 91.4026 90
ZERR 4 0.00039 0.000566 0.00054 0 0.0037 0
LATT 7
SYMM -X,+Y,0.5-Z
SFAC C H N Cl Cu Br I
UNIT 40 24 8 8 4 8 8

L.S. 4 0 0
PLAN  4
CONF
BOND
MORE -1
BOND $H
fmap 2
acta
REM <olex2.extras>
REM <HklSrc "%.\\exp_1504.hkl">
REM </olex2.extras>

WGHT    0.020200
FVAR       1.75060
I2    7    0.154997    0.430583    0.151981    11.00000    0.04882    0.03821 =
         0.03123   -0.00433    0.00586   -0.01516
BR5   6   -0.159087    0.057508   -0.101142    11.00000    0.04893    0.04507 =
         0.02965   -0.00986   -0.00308   -0.00897
CU1   5    0.000000    0.213844    0.250000    10.50000    0.02886    0.02745 =
         0.01594    0.00000    0.00266    0.00000
CL1   4    0.246863    0.152212    0.240906    11.00000    0.03248    0.04489 =
         0.02612    0.00308    0.00542    0.00630
C4    1   -0.002968    0.246498   -0.075628    11.00000    0.04664    0.04097 =
         0.01438    0.00260    0.00111   -0.00196
AFIX  43
H4    2   -0.000134    0.249501   -0.138895    11.00000   -1.20000
AFIX   0
C2    1    0.056484    0.314718    0.071505    11.00000    0.02958    0.02235 =
         0.02471   -0.00040    0.00250   -0.00129
C6    1   -0.076865    0.164447    0.061733    11.00000    0.02769    0.02820 =
         0.02244    0.00367    0.00153   -0.00744
AFIX  43
H6    2   -0.126367    0.110113    0.089827    11.00000   -1.20000
AFIX   0
C3    1    0.063838    0.322907   -0.021765    11.00000    0.04630    0.03669 =
         0.02569    0.00876    0.00369   -0.01004
AFIX  43
H3    2    0.112587    0.378516   -0.048295    11.00000   -1.20000
AFIX   0
C5    1   -0.073341    0.166372   -0.032271    11.00000    0.02739    0.03438 =
         0.02003   -0.00595   -0.00107    0.00144
N1    3   -0.012567    0.236895    0.113921    11.00000    0.02751    0.02341 =
         0.01893    0.00027    0.00149   -0.00052
HKLF 4




REM  exp_1504 in C2/c #15
REM wR2 = 0.0639, GooF = S = 1.013, Restrained GooF = 1.013 for all data
REM R1 = 0.0324 for 1545 Fo > 4sig(Fo) and 0.0454 for all 1901 data
REM 87 parameters refined using 0 restraints

END

WGHT      0.0202      0.0000

REM Highest difference peak  0.499,  deepest hole -0.862,  1-sigma level  0.148
Q1    1  -0.0864  0.0803  0.1214  11.00000  0.05    0.50
Q2    1   0.0580  0.0607  0.2498  11.00000  0.05    0.49
Q3    1   0.0559  0.2871  0.2685  11.00000  0.05    0.48
Q4    1   0.0753  0.3557  0.2095  11.00000  0.05    0.48
;
_shelx_res_checksum              31213
_olex2_date_sample_data_collection 2014-12-18
_olex2_submission_special_instructions 'No special instructions were received'
