#------------------------------------------------------------------------------
#$Date: 2016-03-24 14:32:51 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179667 $
#$URL: svn://www.crystallography.net/cod/cif/4/51/20/4512090.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_4512090
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                 123.529(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   20.7724(15)
_cell_length_b                   13.5800(10)
_cell_length_c                   15.6132(10)
_cell_measurement_reflns_used    6955
_cell_measurement_temperature    195
_cell_measurement_theta_max      27.4019
_cell_measurement_theta_min      2.3523
_cell_volume                     3671.5(5)
_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      195.0
_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 0.996
_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  0.0321
_diffrn_reflns_av_unetI/netI     0.0309
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            18242
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.495
_diffrn_reflns_theta_min         2.012
_diffrn_source                   'X-ray tube'
_diffrn_source_target            Mo
_diffrn_source_type              'Siemens KFF Mo 2K-180'
_exptl_absorpt_coefficient_mu    10.250
_exptl_absorpt_correction_T_max  0.74
_exptl_absorpt_correction_T_min  0.58
_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    2.790
_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         2.244
_refine_diff_density_min         -0.923
_refine_diff_density_rms         0.208
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.223
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         4196
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.223
_refine_ls_R_factor_all          0.0454
_refine_ls_R_factor_gt           0.0350
_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)+(0.0235P)²+87.1097P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0944
_refine_ls_wR_factor_ref         0.0977
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3539
_reflns_number_total             4196
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            cg500905z_si_002.cif
_cod_data_source_block           13mk0603_195k_compond_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_database_code               4512090
#BEGIN Tags that were not found in dictionaries:
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  {H1A,H1B} of C1, H3 of C3, H12 of C12, H9 of C9, H10 of C10, H13 of C13, H4
  of C4, H6 of C6, H7 of C7
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 0.5933(4) 0.3743(6) 0.5647(5) 0.0196(15) Uani 1 1 d . .
H1A H 0.5746 0.4431 0.5541 0.024 Uiso 1 1 calc R U
H1B H 0.5472 0.3313 0.5271 0.024 Uiso 1 1 calc R U
C2 C 0.3608(4) 0.7848(5) 0.2976(6) 0.0188(15) Uani 1 1 d . .
C3 C 0.2944(5) 0.8343(6) 0.2250(6) 0.0269(17) Uani 1 1 d . .
H3 H 0.2490 0.7987 0.1775 0.032 Uiso 1 1 calc R U
C4 C 0.2947(5) 0.9364(6) 0.2219(7) 0.0298(18) Uani 1 1 d . .
H4 H 0.2495 0.9711 0.1722 0.036 Uiso 1 1 calc R U
C5 C 0.3611(5) 0.9873(6) 0.2913(6) 0.0254(17) Uani 1 1 d . .
C6 C 0.4278(5) 0.9380(6) 0.3631(7) 0.0289(18) Uani 1 1 d . .
H6 H 0.4731 0.9739 0.4104 0.035 Uiso 1 1 calc R U
C7 C 0.4285(5) 0.8364(6) 0.3659(6) 0.0269(17) Uani 1 1 d . .
H7 H 0.4746 0.8020 0.4138 0.032 Uiso 1 1 calc R U
C8 C 0.6467(4) 0.2308(5) 0.4889(5) 0.0177(14) Uani 1 1 d . .
C9 C 0.7111(4) 0.1763(5) 0.5600(6) 0.0213(15) Uani 1 1 d . .
H9 H 0.7550 0.2085 0.6158 0.026 Uiso 1 1 calc R U
C10 C 0.7115(5) 0.0746(6) 0.5495(7) 0.0283(18) Uani 1 1 d . .
H10 H 0.7553 0.0368 0.5979 0.034 Uiso 1 1 calc R U
C11 C 0.6468(5) 0.0292(5) 0.4672(6) 0.0237(16) Uani 1 1 d . .
C12 C 0.5839(5) 0.0836(6) 0.3955(6) 0.0259(17) Uani 1 1 d . .
H12 H 0.5406 0.0517 0.3387 0.031 Uiso 1 1 calc R U
C13 C 0.5835(5) 0.1853(6) 0.4059(6) 0.0259(17) Uani 1 1 d . .
H13 H 0.5402 0.2231 0.3563 0.031 Uiso 1 1 calc R U
S1 S 0.35744(11) 0.65339(13) 0.29983(13) 0.0181(4) Uani 1 1 d . .
S2 S 0.64812(10) 0.36044(13) 0.50628(13) 0.0165(3) Uani 1 1 d . .
Cu1 Cu 0.44520(6) 0.58611(7) 0.26902(7) 0.0245(2) Uani 1 1 d . .
Cu2 Cu 0.56166(6) 0.43832(7) 0.35082(7) 0.0220(2) Uani 1 1 d . .
Br1 Br 0.36362(6) 1.12709(6) 0.29039(8) 0.0386(2) Uani 1 1 d . .
Br2 Br 0.64471(6) -0.10989(6) 0.45529(8) 0.0393(2) Uani 1 1 d . .
I1 I 0.59179(3) 0.62607(3) 0.41851(4) 0.02061(12) Uani 1 1 d . .
I2 I 0.41613(3) 0.39288(3) 0.29462(3) 0.01731(12) 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 107.2 . .
S1 C1 H1A 108.0 5_666 .
S1 C1 H1B 108.0 5_666 .
S1 C1 S2 117.3(4) 5_666 .
S2 C1 H1A 108.0 . .
S2 C1 H1B 108.0 . .
C3 C2 C7 120.6(7) . .
C3 C2 S1 118.0(6) . .
C7 C2 S1 121.4(6) . .
C2 C3 H3 120.2 . .
C2 C3 C4 119.6(8) . .
C4 C3 H3 120.2 . .
C3 C4 H4 120.2 . .
C5 C4 C3 119.6(8) . .
C5 C4 H4 120.2 . .
C4 C5 C6 120.9(7) . .
C4 C5 Br1 120.9(6) . .
C6 C5 Br1 118.1(6) . .
C5 C6 H6 120.0 . .
C7 C6 C5 119.9(8) . .
C7 C6 H6 120.0 . .
C2 C7 H7 120.3 . .
C6 C7 C2 119.3(8) . .
C6 C7 H7 120.3 . .
C9 C8 S2 118.5(6) . .
C13 C8 C9 120.6(7) . .
C13 C8 S2 120.9(6) . .
C8 C9 H9 120.0 . .
C8 C9 C10 120.0(7) . .
C10 C9 H9 120.0 . .
C9 C10 H10 120.5 . .
C11 C10 C9 119.0(8) . .
C11 C10 H10 120.5 . .
C10 C11 Br2 119.4(6) . .
C12 C11 C10 120.8(7) . .
C12 C11 Br2 119.8(6) . .
C11 C12 H12 119.9 . .
C11 C12 C13 120.2(8) . .
C13 C12 H12 119.9 . .
C8 C13 C12 119.4(7) . .
C8 C13 H13 120.3 . .
C12 C13 H13 120.3 . .
C1 S1 Cu1 99.2(2) 5_666 .
C2 S1 C1 103.1(3) . 5_666
C2 S1 Cu1 110.3(2) . .
C1 S2 Cu2 98.0(2) . .
C8 S2 C1 102.5(3) . .
C8 S2 Cu2 110.6(2) . .
S1 Cu1 Cu1 156.75(5) . 2_655
S1 Cu1 Cu2 133.86(7) . 2_655
S1 Cu1 Cu2 139.20(6) . .
S1 Cu1 I1 112.71(6) . .
S1 Cu1 I1 111.66(6) . 2_655
S1 Cu1 I2 94.84(6) . .
Cu1 Cu1 Cu2 58.55(3) 2_655 .
Cu1 Cu1 Cu2 64.33(3) 2_655 2_655
Cu1 Cu1 I1 59.42(4) 2_655 .
Cu1 Cu1 I2 108.35(2) 2_655 .
Cu2 Cu1 Cu2 59.46(4) 2_655 .
Cu2 Cu1 I2 57.48(3) 2_655 .
I1 Cu1 Cu1 60.76(4) 2_655 2_655
I1 Cu1 Cu2 107.28(4) 2_655 .
I1 Cu1 Cu2 58.40(3) . .
I1 Cu1 Cu2 60.76(3) 2_655 2_655
I1 Cu1 Cu2 110.80(4) . 2_655
I1 Cu1 I1 114.79(4) 2_655 .
I1 Cu1 I2 113.67(4) 2_655 .
I1 Cu1 I2 107.45(4) . .
I2 Cu1 Cu2 57.75(3) . .
S2 Cu2 Cu1 139.76(6) . .
S2 Cu2 Cu1 140.99(6) . 2_655
S2 Cu2 Cu2 152.60(5) . 2_655
S2 Cu2 I1 98.19(5) . .
S2 Cu2 I2 108.30(5) . .
S2 Cu2 I2 113.05(6) . 2_655
Cu1 Cu2 Cu1 57.12(4) 2_655 .
Cu1 Cu2 Cu2 63.02(3) 2_655 2_655
Cu1 Cu2 I1 58.65(3) 2_655 .
Cu1 Cu2 I2 108.84(4) 2_655 .
Cu2 Cu2 Cu1 57.51(3) 2_655 .
I1 Cu2 Cu1 57.66(3) . .
I1 Cu2 Cu2 108.44(2) . 2_655
I1 Cu2 I2 108.52(4) . .
I2 Cu2 Cu1 106.82(4) 2_655 .
I2 Cu2 Cu1 62.74(3) 2_655 2_655
I2 Cu2 Cu1 59.74(3) . .
I2 Cu2 Cu2 60.53(3) 2_655 2_655
I2 Cu2 Cu2 57.51(3) . 2_655
I2 Cu2 I1 116.55(4) 2_655 .
I2 Cu2 I2 111.30(4) 2_655 .
Cu1 I1 Cu1 59.82(4) 2_655 .
Cu1 I1 Cu2 63.94(3) . .
Cu1 I1 Cu2 60.59(3) 2_655 .
Cu2 I2 Cu1 59.78(3) 2_655 .
Cu2 I2 Cu1 62.51(3) . .
Cu2 I2 Cu2 61.96(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 0.9900 .
C1 H1B 0.9900 .
C1 S1 1.808(7) 5_666
C1 S2 1.820(7) .
C2 C3 1.383(11) .
C2 C7 1.396(11) .
C2 S1 1.786(7) .
C3 H3 0.9500 .
C3 C4 1.388(11) .
C4 H4 0.9500 .
C4 C5 1.379(12) .
C5 C6 1.382(12) .
C5 Br1 1.900(8) .
C6 H6 0.9500 .
C6 C7 1.380(12) .
C7 H7 0.9500 .
C8 C9 1.389(10) .
C8 C13 1.380(10) .
C8 S2 1.779(7) .
C9 H9 0.9500 .
C9 C10 1.391(11) .
C10 H10 0.9500 .
C10 C11 1.390(12) .
C11 C12 1.375(11) .
C11 Br2 1.896(7) .
C12 H12 0.9500 .
C12 C13 1.391(11) .
C13 H13 0.9500 .
S1 C1 1.808(7) 5_666
S1 Cu1 2.315(2) .
S2 Cu2 2.328(2) .
Cu1 Cu1 2.6515(19) 2_655
Cu1 Cu2 2.8457(14) .
Cu1 Cu2 2.6934(13) 2_655
Cu1 I1 2.6763(11) .
Cu1 I1 2.6406(11) 2_655
Cu1 I2 2.7707(11) .
Cu2 Cu1 2.6934(13) 2_655
Cu2 Cu2 2.7503(19) 2_655
Cu2 I1 2.6979(11) .
Cu2 I2 2.7128(11) .
Cu2 I2 2.6282(10) 2_655
I1 Cu1 2.6406(11) 2_655
I2 Cu2 2.6283(10) 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 -0.1(12) . .
C3 C2 C7 C6 2.7(12) . .
C3 C2 S1 C1 -135.9(6) . 5_666
C3 C2 S1 Cu1 119.0(6) . .
C3 C4 C5 C6 1.0(12) . .
C3 C4 C5 Br1 -179.5(6) . .
C4 C5 C6 C7 -0.1(12) . .
C5 C6 C7 C2 -1.7(12) . .
C7 C2 C3 C4 -1.7(12) . .
C7 C2 S1 C1 45.0(7) . 5_666
C7 C2 S1 Cu1 -60.0(6) . .
C8 C9 C10 C11 0.1(12) . .
C9 C8 C13 C12 1.9(11) . .
C9 C8 S2 C1 -99.7(6) . .
C9 C8 S2 Cu2 156.7(5) . .
C9 C10 C11 C12 1.5(12) . .
C9 C10 C11 Br2 -177.3(6) . .
C10 C11 C12 C13 -1.5(12) . .
C11 C12 C13 C8 -0.2(12) . .
C13 C8 C9 C10 -1.8(11) . .
C13 C8 S2 C1 81.2(7) . .
C13 C8 S2 Cu2 -22.5(7) . .
S1 C1 S2 C8 78.3(5) 5_666 .
S1 C1 S2 Cu2 -168.3(4) 5_666 .
S1 C2 C3 C4 179.2(6) . .
S1 C2 C7 C6 -178.3(6) . .
S2 C8 C9 C10 179.1(6) . .
S2 C8 C13 C12 -179.0(6) . .
Br1 C5 C6 C7 -179.6(6) . .
Br2 C11 C12 C13 177.3(6) . .
