#------------------------------------------------------------------------------
#$Date: 2016-03-24 14:32:51 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179667 $
#$URL: svn://www.crystallography.net/cod/cif/4/51/20/4512091.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_4512091
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                 123.622(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   20.843(2)
_cell_length_b                   13.5799(15)
_cell_length_c                   15.6226(15)
_cell_measurement_reflns_used    6064
_cell_measurement_temperature    235
_cell_measurement_theta_max      27.3682
_cell_measurement_theta_min      2.3470
_cell_volume                     3682.2(7)
_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 0.996
_diffrn_measured_fraction_theta_max 0.993
_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  0.0304
_diffrn_reflns_av_unetI/netI     0.0336
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.993
_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            16493
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.565
_diffrn_reflns_theta_min         2.011
_diffrn_source                   'X-ray tube'
_diffrn_source_target            Mo
_diffrn_source_type              'Siemens KFF Mo 2K-180'
_exptl_absorpt_coefficient_mu    10.220
_exptl_absorpt_correction_T_max  0.74
_exptl_absorpt_correction_T_min  0.57
_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    2.782
_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         2.047
_refine_diff_density_min         -1.072
_refine_diff_density_rms         0.213
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.256
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         4234
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.256
_refine_ls_R_factor_all          0.0529
_refine_ls_R_factor_gt           0.0385
_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)+(0.0301P)²+78.7720P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1055
_refine_ls_wR_factor_ref         0.1107
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3465
_reflns_number_total             4234
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            cg500905z_si_002.cif
_cod_data_source_block           13mk0603_235k_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        3682.1(7)
_cod_database_code               4512091
#BEGIN Tags that were not found in dictionaries:
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  H6 of C6, H10 of C10, H12 of C12, H3 of C3, H7 of C7, H4 of C4, H13 of C13,
  {H1A,H1B} of C1, 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)
;
#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 0.5926(5) 0.3740(6) 0.5640(6) 0.0237(17) Uani 1 1 d . .
H1A H 0.5741 0.4421 0.5534 0.028 Uiso 1 1 calc R U
H1B H 0.5472 0.3314 0.5264 0.028 Uiso 1 1 calc R U
C2 C 0.3609(5) 0.7851(6) 0.2976(6) 0.0230(16) Uani 1 1 d . .
C3 C 0.2950(5) 0.8342(7) 0.2257(7) 0.032(2) Uani 1 1 d . .
H3 H 0.2502 0.7989 0.1784 0.038 Uiso 1 1 calc R U
C4 C 0.2950(6) 0.9368(7) 0.2230(8) 0.037(2) Uani 1 1 d . .
H4 H 0.2501 0.9711 0.1744 0.045 Uiso 1 1 calc R U
C5 C 0.3612(6) 0.9876(6) 0.2921(7) 0.0294(19) Uani 1 1 d . .
C6 C 0.4276(5) 0.9383(7) 0.3627(7) 0.033(2) Uani 1 1 d . .
H6 H 0.4725 0.9737 0.4093 0.040 Uiso 1 1 calc R U
C7 C 0.4283(5) 0.8377(7) 0.3650(7) 0.032(2) Uani 1 1 d . .
H7 H 0.4741 0.8039 0.4118 0.038 Uiso 1 1 calc R U
C8 C 0.6466(4) 0.2306(6) 0.4889(6) 0.0193(15) Uani 1 1 d . .
C9 C 0.7104(5) 0.1770(6) 0.5592(7) 0.0247(17) Uani 1 1 d . .
H9 H 0.7534 0.2091 0.6145 0.030 Uiso 1 1 calc R U
C10 C 0.7115(5) 0.0745(6) 0.5488(8) 0.032(2) Uani 1 1 d . .
H10 H 0.7551 0.0375 0.5966 0.038 Uiso 1 1 calc R U
C11 C 0.6476(5) 0.0291(6) 0.4673(7) 0.0278(18) Uani 1 1 d . .
C12 C 0.5841(6) 0.0835(6) 0.3960(7) 0.032(2) Uani 1 1 d . .
H12 H 0.5411 0.0521 0.3399 0.038 Uiso 1 1 calc R U
C13 C 0.5839(5) 0.1842(7) 0.4073(7) 0.0309(19) Uani 1 1 d . .
H13 H 0.5407 0.2212 0.3587 0.037 Uiso 1 1 calc R U
S1 S 0.35792(12) 0.65407(15) 0.29988(15) 0.0219(4) Uani 1 1 d . .
S2 S 0.64785(11) 0.36036(14) 0.50661(15) 0.0193(4) Uani 1 1 d . .
Cu1 Cu 0.44522(6) 0.58665(8) 0.26894(8) 0.0297(3) Uani 1 1 d . .
Cu2 Cu 0.56172(6) 0.43865(8) 0.35109(8) 0.0271(2) Uani 1 1 d . .
Br1 Br 0.36365(7) 1.12711(7) 0.29090(10) 0.0468(3) Uani 1 1 d . .
Br2 Br 0.64500(7) -0.10924(7) 0.45484(9) 0.0480(3) Uani 1 1 d . .
I1 I 0.59158(3) 0.62635(4) 0.41843(4) 0.02485(14) Uani 1 1 d . .
I2 I 0.41624(3) 0.39332(4) 0.29421(4) 0.02097(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 .
S1 C1 S2 116.9(4) 5_666 .
S2 C1 H1A 108.1 . .
S2 C1 H1B 108.1 . .
C3 C2 C7 120.1(8) . .
C3 C2 S1 118.1(7) . .
C7 C2 S1 121.8(6) . .
C2 C3 H3 120.2 . .
C2 C3 C4 119.6(9) . .
C4 C3 H3 120.2 . .
C3 C4 H4 120.2 . .
C5 C4 C3 119.6(9) . .
C5 C4 H4 120.2 . .
C4 C5 Br1 120.9(7) . .
C6 C5 C4 120.7(8) . .
C6 C5 Br1 118.3(7) . .
C5 C6 H6 120.0 . .
C7 C6 C5 120.0(9) . .
C7 C6 H6 120.0 . .
C2 C7 H7 120.0 . .
C6 C7 C2 120.0(8) . .
C6 C7 H7 120.0 . .
C9 C8 S2 118.4(6) . .
C13 C8 C9 120.0(8) . .
C13 C8 S2 121.6(6) . .
C8 C9 H9 119.9 . .
C8 C9 C10 120.3(8) . .
C10 C9 H9 119.9 . .
C9 C10 H10 120.6 . .
C11 C10 C9 118.8(8) . .
C11 C10 H10 120.6 . .
C10 C11 C12 120.6(8) . .
C10 C11 Br2 120.0(7) . .
C12 C11 Br2 119.4(7) . .
C11 C12 H12 120.1 . .
C13 C12 C11 119.8(9) . .
C13 C12 H12 120.1 . .
C8 C13 C12 120.4(8) . .
C8 C13 H13 119.8 . .
C12 C13 H13 119.8 . .
C1 S1 Cu1 99.2(3) 5_666 .
C2 S1 C1 103.2(4) . 5_666
C2 S1 Cu1 110.5(3) . .
C1 S2 Cu2 97.8(3) . .
C8 S2 C1 102.6(4) . .
C8 S2 Cu2 110.6(3) . .
S1 Cu1 Cu1 156.70(6) . 2_655
S1 Cu1 Cu2 133.96(7) . 2_655
S1 Cu1 Cu2 139.18(7) . .
S1 Cu1 I1 112.72(7) . .
S1 Cu1 I1 111.82(7) . 2_655
S1 Cu1 I2 94.96(6) . .
Cu1 Cu1 Cu2 58.51(4) 2_655 .
Cu1 Cu1 Cu2 64.35(4) 2_655 2_655
Cu1 Cu1 I1 59.30(4) 2_655 .
Cu1 Cu1 I2 108.28(2) 2_655 .
Cu2 Cu1 Cu2 59.49(5) 2_655 .
Cu2 Cu1 I2 57.39(3) 2_655 .
I1 Cu1 Cu1 60.71(4) 2_655 2_655
I1 Cu1 Cu2 110.69(5) . 2_655
I1 Cu1 Cu2 58.27(3) . .
I1 Cu1 Cu2 60.68(3) 2_655 2_655
I1 Cu1 Cu2 107.18(4) 2_655 .
I1 Cu1 I1 114.69(4) 2_655 .
I1 Cu1 I2 113.53(4) 2_655 .
I1 Cu1 I2 107.44(4) . .
I2 Cu1 Cu2 57.76(3) . .
S2 Cu2 Cu1 139.78(7) . .
S2 Cu2 Cu1 141.16(7) . 2_655
S2 Cu2 Cu2 152.44(6) . 2_655
S2 Cu2 I1 98.42(6) . .
S2 Cu2 I2 113.07(6) . 2_655
S2 Cu2 I2 108.29(6) . .
Cu1 Cu2 Cu1 57.14(5) 2_655 .
Cu1 Cu2 Cu2 63.04(4) 2_655 2_655
Cu1 Cu2 I2 108.72(4) 2_655 .
Cu2 Cu2 Cu1 57.47(4) 2_655 .
I1 Cu2 Cu1 58.58(3) . 2_655
I1 Cu2 Cu1 57.60(3) . .
I1 Cu2 Cu2 108.33(3) . 2_655
I1 Cu2 I2 108.46(4) . .
I2 Cu2 Cu1 106.80(4) 2_655 .
I2 Cu2 Cu1 59.63(3) . .
I2 Cu2 Cu1 62.71(3) 2_655 2_655
I2 Cu2 Cu2 60.56(4) 2_655 2_655
I2 Cu2 Cu2 57.35(4) . 2_655
I2 Cu2 I1 116.48(4) 2_655 .
I2 Cu2 I2 111.21(4) 2_655 .
Cu1 I1 Cu1 59.99(4) 2_655 .
Cu1 I1 Cu2 64.13(3) . .
Cu1 I1 Cu2 60.74(3) 2_655 .
Cu2 I2 Cu1 59.90(3) 2_655 .
Cu2 I2 Cu1 62.61(3) . .
Cu2 I2 Cu2 62.09(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 1.818(8) 5_666
C1 S2 1.818(8) .
C2 C3 1.373(12) .
C2 C7 1.398(12) .
C2 S1 1.781(8) .
C3 H3 0.9400 .
C3 C4 1.394(13) .
C4 H4 0.9400 .
C4 C5 1.377(14) .
C5 C6 1.375(13) .
C5 Br1 1.895(8) .
C6 H6 0.9400 .
C6 C7 1.366(13) .
C7 H7 0.9400 .
C8 C9 1.374(11) .
C8 C13 1.373(11) .
C8 S2 1.781(8) .
C9 H9 0.9400 .
C9 C10 1.402(12) .
C10 H10 0.9400 .
C10 C11 1.378(13) .
C11 C12 1.381(13) .
C11 Br2 1.886(8) .
C12 H12 0.9400 .
C12 C13 1.378(13) .
C13 H13 0.9400 .
S1 C1 1.818(8) 5_666
S1 Cu1 2.315(2) .
S2 Cu2 2.329(2) .
Cu1 Cu1 2.657(2) 2_655
Cu1 Cu2 2.8515(15) .
Cu1 Cu2 2.6974(15) 2_655
Cu1 I1 2.6759(13) .
Cu1 I1 2.6383(12) 2_655
Cu1 I2 2.7708(13) .
Cu2 Cu1 2.6973(15) 2_655
Cu2 Cu2 2.756(2) 2_655
Cu2 I1 2.6956(12) .
Cu2 I2 2.7163(12) .
Cu2 I2 2.6263(11) 2_655
I1 Cu1 2.6384(12) 2_655
I2 Cu2 2.6262(11) 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 0.5(14) . .
C3 C2 C7 C6 3.4(13) . .
C3 C2 S1 C1 -135.7(7) . 5_666
C3 C2 S1 Cu1 119.0(6) . .
C3 C4 C5 C6 1.0(14) . .
C3 C4 C5 Br1 179.9(7) . .
C4 C5 C6 C7 -0.3(14) . .
C5 C6 C7 C2 -1.9(14) . .
C7 C2 C3 C4 -2.7(13) . .
C7 C2 S1 C1 45.8(8) . 5_666
C7 C2 S1 Cu1 -59.4(7) . .
C8 C9 C10 C11 -0.2(13) . .
C9 C8 C13 C12 0.9(13) . .
C9 C8 S2 C1 -100.2(7) . .
C9 C8 S2 Cu2 156.3(6) . .
C9 C10 C11 C12 1.3(13) . .
C9 C10 C11 Br2 -176.8(6) . .
C10 C11 C12 C13 -1.2(13) . .
C11 C12 C13 C8 0.1(14) . .
C13 C8 C9 C10 -0.9(12) . .
C13 C8 S2 C1 79.9(7) . .
C13 C8 S2 Cu2 -23.5(7) . .
S1 C1 S2 C8 78.5(5) 5_666 .
S1 C1 S2 Cu2 -168.3(4) 5_666 .
S1 C2 C3 C4 178.9(7) . .
S1 C2 C7 C6 -178.2(7) . .
S2 C8 C9 C10 179.3(6) . .
S2 C8 C13 C12 -179.2(7) . .
Br1 C5 C6 C7 -179.2(7) . .
Br2 C11 C12 C13 176.9(7) . .
