#------------------------------------------------------------------------------
#$Date: 2016-03-24 14:32:51 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179667 $
#$URL: svn://www.crystallography.net/cod/cif/4/51/20/4512092.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4512092
loop_
_publ_author_name
'Knorr, Michael'
'Khatyr, Abderrahim'
'Dini Aleo, Ahmed'
'El Yaagoubi, Anass'
'Strohmann, Carsten'
'Kubicki, Marek M.'
'Rousselin, Yoann'
'Aly, Shawkat M.'
'Fortin, Daniel'
'Lapprand, Antony'
'Harvey, Pierre D.'
_publ_section_title
;
 Copper(I) Halides (X = Br, I) Coordinated to Bis(arylthio)methane
 Ligands: Aryl Substitution and Halide Effects on the Dimensionality,
 Cluster Size, and Luminescence Properties of the Coordination Polymers
;
_journal_issue                   11
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              5373
_journal_paper_doi               10.1021/cg500905z
_journal_volume                  14
_journal_year                    2014
_chemical_formula_moiety         'C13 H10 Br2 Cu2 I2 S2'
_chemical_formula_sum            'C13 H10 Br2 Cu2 I2 S2'
_chemical_formula_weight         771.03
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2013-03-13
_audit_creation_method
;
  Olex2 1.2
  (compiled 2012.12.05 svn.r2549, GUI svn.r4385)
;
_audit_update_record
;
2013-03-13 # Formatted by publCIF
;
_cell_angle_alpha                90
_cell_angle_beta                 123.704(4)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   20.941(4)
_cell_length_b                   13.579(3)
_cell_length_c                   15.667(3)
_cell_measurement_reflns_used    7662
_cell_measurement_temperature    235
_cell_measurement_theta_max      27.4844
_cell_measurement_theta_min      2.3382
_cell_volume                     3706.2(13)
_computing_cell_refinement       'SAINT V8.27B (Bruker AXS Inc., 2012)'
_computing_data_collection       'SAINT V8.27B (Bruker AXS Inc., 2012)'
_computing_data_reduction        'SAINT V8.27B (Bruker AXS Inc., 2012)'
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
'SHELXS-97, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122'
_diffrn_ambient_temperature      235.0
_diffrn_detector                 'CCD Plate'
_diffrn_detector_area_resol_mean 9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Nonius Kappa Apex II'
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_radiation_collimation    '0.6 mm'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a~1~'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_reflns_av_R_equivalents  0.0258
_diffrn_reflns_av_unetI/netI     0.0258
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            17157
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.554
_diffrn_reflns_theta_min         2.007
_diffrn_source                   'X-ray tube'
_diffrn_source_target            Mo
_diffrn_source_type              'Siemens KFF Mo 2K-180'
_exptl_absorpt_coefficient_mu    10.154
_exptl_absorpt_correction_T_max  0.74
_exptl_absorpt_correction_T_min  0.56
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.764
_exptl_crystal_density_meas      ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             2832
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_refine_diff_density_max         1.895
_refine_diff_density_min         -1.181
_refine_diff_density_rms         0.209
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.244
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         4256
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.244
_refine_ls_R_factor_all          0.0462
_refine_ls_R_factor_gt           0.0366
_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)+(0.0330P)²+82.3520P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1121
_refine_ls_wR_factor_ref         0.1160
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3623
_reflns_number_total             4256
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            cg500905z_si_002.cif
_cod_data_source_block           13mk0603_275k_compound_4
_cod_depositor_comments
;Adding full bibliography for 4512075--4512092.cif.

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_cell_volume        3706.2(11)
_cod_database_code               4512092
#BEGIN Tags that were not found in dictionaries:
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  H12 of C12, H13 of C13, H4 of C4, H10 of C10, {H1A,H1B} of C1, H7 of C7, H6
  of C6, H3 of C3, H9 of C9
2.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C7(H7), C9(H9), C10(H10), C12(H12), C13(H13)
;
_shelx_estimated_absorpt_t_max   0.311
_shelx_estimated_absorpt_t_min   0.236
#END Tags that were not found in dictionaries
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'
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
C1 C 0.5924(4) 0.3733(6) 0.5634(6) 0.0261(16) Uani 1 1 d . .
H1A H 0.5474 0.3302 0.5259 0.031 Uiso 1 1 calc R U
H1B H 0.5735 0.4412 0.5525 0.031 Uiso 1 1 calc R U
C2 C 0.3616(5) 0.7857(6) 0.2979(6) 0.0274(16) Uani 1 1 d . .
C3 C 0.2953(5) 0.8350(7) 0.2268(7) 0.040(2) Uani 1 1 d . .
H3 H 0.2504 0.7997 0.1803 0.048 Uiso 1 1 calc R U
C4 C 0.2956(6) 0.9381(7) 0.2244(8) 0.043(2) Uani 1 1 d . .
H4 H 0.2508 0.9726 0.1762 0.052 Uiso 1 1 calc R U
C5 C 0.3615(5) 0.9882(6) 0.2925(7) 0.0346(19) Uani 1 1 d . .
C6 C 0.4273(6) 0.9388(7) 0.3622(8) 0.041(2) Uani 1 1 d . .
H6 H 0.4721 0.9743 0.4087 0.049 Uiso 1 1 calc R U
C7 C 0.4284(5) 0.8381(7) 0.3648(7) 0.039(2) Uani 1 1 d . .
H7 H 0.4742 0.8045 0.4115 0.047 Uiso 1 1 calc R U
C8 C 0.6464(4) 0.2309(6) 0.4884(6) 0.0253(15) Uani 1 1 d . .
C9 C 0.7107(5) 0.1774(6) 0.5592(7) 0.0317(17) Uani 1 1 d . .
H9 H 0.7538 0.2092 0.6145 0.038 Uiso 1 1 calc R U
C10 C 0.7106(5) 0.0750(7) 0.5471(8) 0.041(2) Uani 1 1 d . .
H10 H 0.7540 0.0376 0.5942 0.049 Uiso 1 1 calc R U
C11 C 0.6473(5) 0.0295(6) 0.4665(7) 0.0346(19) Uani 1 1 d . .
C12 C 0.5844(6) 0.0840(7) 0.3962(7) 0.039(2) Uani 1 1 d . .
H12 H 0.5415 0.0524 0.3404 0.047 Uiso 1 1 calc R U
C13 C 0.5837(5) 0.1841(7) 0.4068(7) 0.039(2) Uani 1 1 d . .
H13 H 0.5404 0.2209 0.3583 0.046 Uiso 1 1 calc R U
S1 S 0.35819(11) 0.65457(15) 0.29977(15) 0.0266(4) Uani 1 1 d . .
S2 S 0.64751(11) 0.36040(13) 0.50684(14) 0.0241(4) Uani 1 1 d . .
Cu1 Cu 0.44525(7) 0.58724(8) 0.26893(8) 0.0364(3) Uani 1 1 d . .
Cu2 Cu 0.56176(6) 0.43888(8) 0.35138(8) 0.0332(2) Uani 1 1 d . .
Br1 Br 0.36365(7) 1.12721(7) 0.29144(10) 0.0562(3) Uani 1 1 d . .
Br2 Br 0.64517(8) -0.10857(7) 0.45423(10) 0.0576(3) Uani 1 1 d . .
I1 I 0.59138(3) 0.62668(4) 0.41838(4) 0.03043(14) Uani 1 1 d . .
I2 I 0.41642(3) 0.39381(4) 0.29384(4) 0.02569(13) Uani 1 1 d . .
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'
S S 0.1246 0.1234 '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'
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
H1A C1 H1B 107.3 . .
S1 C1 H1A 108.1 5_666 .
S1 C1 H1B 108.1 5_666 .
S2 C1 H1A 108.1 . .
S2 C1 H1B 108.1 . .
S2 C1 S1 116.9(4) . 5_666
C3 C2 C7 120.1(8) . .
C3 C2 S1 117.8(7) . .
C7 C2 S1 122.1(6) . .
C2 C3 H3 120.3 . .
C2 C3 C4 119.3(9) . .
C4 C3 H3 120.3 . .
C3 C4 H4 120.2 . .
C5 C4 C3 119.6(8) . .
C5 C4 H4 120.2 . .
C4 C5 Br1 120.6(7) . .
C6 C5 C4 120.8(8) . .
C6 C5 Br1 118.6(7) . .
C5 C6 H6 119.8 . .
C7 C6 C5 120.5(9) . .
C7 C6 H6 119.8 . .
C2 C7 H7 120.1 . .
C6 C7 C2 119.7(8) . .
C6 C7 H7 120.1 . .
C9 C8 S2 118.0(6) . .
C13 C8 C9 120.3(8) . .
C13 C8 S2 121.7(6) . .
C8 C9 H9 120.5 . .
C8 C9 C10 119.0(8) . .
C10 C9 H9 120.5 . .
C9 C10 H10 120.0 . .
C11 C10 C9 120.0(8) . .
C11 C10 H10 120.0 . .
C10 C11 C12 120.2(8) . .
C10 C11 Br2 120.0(7) . .
C12 C11 Br2 119.8(7) . .
C11 C12 H12 119.8 . .
C13 C12 C11 120.4(9) . .
C13 C12 H12 119.8 . .
C8 C13 H13 120.0 . .
C12 C13 C8 120.1(8) . .
C12 C13 H13 120.0 . .
C1 S1 Cu1 99.4(2) 5_666 .
C2 S1 C1 102.9(4) . 5_666
C2 S1 Cu1 110.3(3) . .
C1 S2 Cu2 97.8(2) . .
C8 S2 C1 102.7(4) . .
C8 S2 Cu2 110.4(3) . .
S1 Cu1 Cu1 156.76(6) . 2_655
S1 Cu1 Cu2 133.94(7) . 2_655
S1 Cu1 Cu2 139.13(7) . .
S1 Cu1 I1 112.83(7) . .
S1 Cu1 I1 111.98(7) . 2_655
S1 Cu1 I2 94.96(6) . .
Cu1 Cu1 Cu2 58.50(4) 2_655 .
Cu1 Cu1 Cu2 64.30(4) 2_655 2_655
Cu1 Cu1 I1 59.25(5) 2_655 .
Cu1 Cu1 I2 108.22(2) 2_655 .
Cu2 Cu1 Cu2 59.56(5) 2_655 .
Cu2 Cu1 I2 57.36(3) 2_655 .
I1 Cu1 Cu1 60.59(4) 2_655 2_655
I1 Cu1 Cu2 110.58(5) . 2_655
I1 Cu1 Cu2 58.12(4) . .
I1 Cu1 Cu2 60.50(4) 2_655 2_655
I1 Cu1 Cu2 107.06(4) 2_655 .
I1 Cu1 I1 114.62(4) 2_655 .
I1 Cu1 I2 113.37(4) 2_655 .
I1 Cu1 I2 107.39(4) . .
I2 Cu1 Cu2 57.77(3) . .
S2 Cu2 Cu1 139.73(7) . .
S2 Cu2 Cu1 141.28(7) . 2_655
S2 Cu2 Cu2 152.39(5) . 2_655
S2 Cu2 I1 98.53(6) . .
S2 Cu2 I2 113.23(6) . 2_655
S2 Cu2 I2 108.35(6) . .
Cu1 Cu2 Cu1 57.19(5) 2_655 .
Cu1 Cu2 Cu2 62.98(4) 2_655 2_655
Cu1 Cu2 I2 108.55(5) 2_655 .
Cu2 Cu2 Cu1 57.46(4) 2_655 .
I1 Cu2 Cu1 58.59(4) . 2_655
I1 Cu2 Cu1 57.58(3) . .
I1 Cu2 Cu2 108.26(3) . 2_655
I1 Cu2 I2 108.37(4) . .
I2 Cu2 Cu1 106.70(4) 2_655 .
I2 Cu2 Cu1 59.47(4) . .
I2 Cu2 Cu1 62.55(4) 2_655 2_655
I2 Cu2 Cu2 60.49(4) 2_655 2_655
I2 Cu2 Cu2 57.23(4) . 2_655
I2 Cu2 I1 116.36(4) 2_655 .
I2 Cu2 I2 111.13(4) 2_655 .
Cu1 I1 Cu1 60.16(4) 2_655 .
Cu1 I1 Cu2 64.30(4) . .
Cu1 I1 Cu2 60.91(3) 2_655 .
Cu2 I2 Cu1 60.09(3) 2_655 .
Cu2 I2 Cu1 62.77(3) . .
Cu2 I2 Cu2 62.28(4) 2_655 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 H1A 0.9800 .
C1 H1B 0.9800 .
C1 S1 1.829(8) 5_666
C1 S2 1.813(8) .
C2 C3 1.378(11) .
C2 C7 1.392(12) .
C2 S1 1.783(8) .
C3 H3 0.9400 .
C3 C4 1.401(13) .
C4 H4 0.9400 .
C4 C5 1.369(14) .
C5 C6 1.368(13) .
C5 Br1 1.889(8) .
C6 H6 0.9400 .
C6 C7 1.367(13) .
C7 H7 0.9400 .
C8 C9 1.383(11) .
C8 C13 1.378(12) .
C8 S2 1.780(8) .
C9 H9 0.9400 .
C9 C10 1.403(12) .
C10 H10 0.9400 .
C10 C11 1.369(13) .
C11 C12 1.374(13) .
C11 Br2 1.882(8) .
C12 H12 0.9400 .
C12 C13 1.371(13) .
C13 H13 0.9400 .
S1 C1 1.829(8) 5_666
S1 Cu1 2.317(2) .
S2 Cu2 2.332(2) .
Cu1 Cu1 2.668(2) 2_655
Cu1 Cu2 2.8605(16) .
Cu1 Cu2 2.7068(15) 2_655
Cu1 I1 2.6798(13) .
Cu1 I1 2.6436(13) 2_655
Cu1 I2 2.7709(13) .
Cu2 Cu1 2.7068(15) 2_655
Cu2 Cu2 2.768(2) 2_655
Cu2 I1 2.6959(13) .
Cu2 I2 2.7213(13) .
Cu2 I2 2.6294(12) 2_655
I1 Cu1 2.6435(13) 2_655
I2 Cu2 2.6295(12) 2_655
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_4
C2 C3 C4 C5 0.0(15) . .
C3 C2 C7 C6 2.6(14) . .
C3 C2 S1 C1 -134.6(7) . 5_666
C3 C2 S1 Cu1 120.1(7) . .
C3 C4 C5 C6 0.7(15) . .
C3 C4 C5 Br1 -179.8(7) . .
C4 C5 C6 C7 0.2(15) . .
C5 C6 C7 C2 -1.9(15) . .
C7 C2 C3 C4 -1.6(14) . .
C7 C2 S1 C1 46.0(8) . 5_666
C7 C2 S1 Cu1 -59.3(7) . .
C8 C9 C10 C11 -0.4(13) . .
C9 C8 C13 C12 1.0(13) . .
C9 C8 S2 C1 -100.5(7) . .
C9 C8 S2 Cu2 156.0(6) . .
C9 C10 C11 C12 1.4(14) . .
C9 C10 C11 Br2 -176.7(7) . .
C10 C11 C12 C13 -1.1(14) . .
C11 C12 C13 C8 -0.1(14) . .
C13 C8 C9 C10 -0.7(12) . .
C13 C8 S2 C1 79.3(7) . .
C13 C8 S2 Cu2 -24.2(7) . .
S1 C1 S2 C8 79.0(5) 5_666 .
S1 C1 S2 Cu2 -167.9(4) 5_666 .
S1 C2 C3 C4 178.9(7) . .
S1 C2 C7 C6 -178.0(7) . .
S2 C8 C9 C10 179.0(7) . .
S2 C8 C13 C12 -178.8(7) . .
Br1 C5 C6 C7 -179.3(7) . .
Br2 C11 C12 C13 177.0(7) . .
