#------------------------------------------------------------------------------
#$Date: 2016-03-24 14:32:51 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179667 $
#$URL: svn://www.crystallography.net/cod/cif/4/51/20/4512089.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_4512089
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                 123.481(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   20.6980(13)
_cell_length_b                   13.5689(9)
_cell_length_c                   15.5919(9)
_cell_measurement_reflns_used    9894
_cell_measurement_temperature    155
_cell_measurement_theta_max      27.5178
_cell_measurement_theta_min      2.3595
_cell_volume                     3652.4(4)
_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      155.0
_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 0.988
_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  0.0260
_diffrn_reflns_av_unetI/netI     0.0230
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.988
_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            18678
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.607
_diffrn_reflns_theta_min         2.015
_diffrn_source                   'X-ray tube'
_diffrn_source_target            Mo
_diffrn_source_type              'Siemens KFF Mo 2K-180'
_exptl_absorpt_coefficient_mu    10.303
_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    2.804
_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         2.506
_refine_diff_density_min         -0.945
_refine_diff_density_rms         0.210
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.255
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         4193
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.255
_refine_ls_R_factor_all          0.0355
_refine_ls_R_factor_gt           0.0311
_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)+(0.0205P)²+87.0800P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0876
_refine_ls_wR_factor_ref         0.0891
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3797
_reflns_number_total             4193
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            cg500905z_si_002.cif
_cod_data_source_block           13mk0603_155k_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_database_code               4512089
#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, H4 of C4, H6 of C6, H7 of C7, H9 of C9, H10 of
  C10, H12 of C12, H13 of C13
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 0.5932(4) 0.3747(5) 0.5648(5) 0.0158(12) Uani 1 1 d . .
H1A H 0.5745 0.4436 0.5542 0.019 Uiso 1 1 calc R U
H1B H 0.5471 0.3317 0.5274 0.019 Uiso 1 1 calc R U
C2 C 0.3608(4) 0.7844(5) 0.2978(5) 0.0145(12) Uani 1 1 d . .
C3 C 0.2943(4) 0.8344(5) 0.2248(5) 0.0220(14) Uani 1 1 d . .
H3 H 0.2487 0.7987 0.1775 0.026 Uiso 1 1 calc R U
C4 C 0.2944(4) 0.9365(5) 0.2208(6) 0.0236(15) Uani 1 1 d . .
H4 H 0.2491 0.9711 0.1706 0.028 Uiso 1 1 calc R U
C5 C 0.3612(4) 0.9871(5) 0.2906(5) 0.0204(14) Uani 1 1 d . .
C6 C 0.4279(4) 0.9375(5) 0.3635(6) 0.0232(15) Uani 1 1 d . .
H6 H 0.4732 0.9734 0.4115 0.028 Uiso 1 1 calc R U
C7 C 0.4282(4) 0.8358(5) 0.3659(5) 0.0218(14) Uani 1 1 d . .
H7 H 0.4742 0.8012 0.4140 0.026 Uiso 1 1 calc R U
C8 C 0.6467(4) 0.2306(5) 0.4888(5) 0.0146(12) Uani 1 1 d . .
C9 C 0.7114(4) 0.1760(5) 0.5599(5) 0.0171(13) Uani 1 1 d . .
H9 H 0.7557 0.2083 0.6152 0.021 Uiso 1 1 calc R U
C10 C 0.7112(4) 0.0735(5) 0.5499(6) 0.0227(15) Uani 1 1 d . .
H10 H 0.7547 0.0355 0.5989 0.027 Uiso 1 1 calc R U
C11 C 0.6468(4) 0.0283(5) 0.4679(5) 0.0187(13) Uani 1 1 d . .
C12 C 0.5833(4) 0.0828(5) 0.3950(5) 0.0222(14) Uani 1 1 d . .
H12 H 0.5400 0.0507 0.3382 0.027 Uiso 1 1 calc R U
C13 C 0.5833(4) 0.1845(5) 0.4052(5) 0.0208(14) Uani 1 1 d . .
H13 H 0.5401 0.2223 0.3551 0.025 Uiso 1 1 calc R U
S1 S 0.35702(9) 0.65286(12) 0.29989(12) 0.0141(3) Uani 1 1 d . .
S2 S 0.64833(9) 0.36060(11) 0.50592(12) 0.0127(3) Uani 1 1 d . .
Cu1 Cu 0.44525(5) 0.58543(6) 0.26912(6) 0.01905(18) Uani 1 1 d . .
Cu2 Cu 0.56158(5) 0.43813(6) 0.35053(6) 0.01730(17) Uani 1 1 d . .
Br1 Br 0.36359(5) 1.12696(5) 0.28992(7) 0.03034(18) Uani 1 1 d . .
Br2 Br 0.64448(5) -0.11044(5) 0.45573(7) 0.03098(18) Uani 1 1 d . .
I1 I 0.59197(2) 0.62583(3) 0.41851(3) 0.01621(10) Uani 1 1 d . .
I2 I 0.41594(2) 0.39245(3) 0.29495(3) 0.01348(10) 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 108.0 5_666 .
S1 C1 H1B 108.0 5_666 .
S1 C1 S2 117.0(3) 5_666 .
S2 C1 H1A 108.0 . .
S2 C1 H1B 108.0 . .
C3 C2 C7 120.4(6) . .
C3 C2 S1 118.0(5) . .
C7 C2 S1 121.5(5) . .
C2 C3 H3 120.0 . .
C2 C3 C4 120.0(7) . .
C4 C3 H3 120.0 . .
C3 C4 H4 120.4 . .
C5 C4 C3 119.1(7) . .
C5 C4 H4 120.4 . .
C4 C5 C6 121.1(6) . .
C4 C5 Br1 120.7(5) . .
C6 C5 Br1 118.2(6) . .
C5 C6 H6 120.2 . .
C7 C6 C5 119.7(7) . .
C7 C6 H6 120.2 . .
C2 C7 H7 120.2 . .
C6 C7 C2 119.6(6) . .
C6 C7 H7 120.2 . .
C9 C8 S2 118.5(5) . .
C13 C8 C9 120.3(6) . .
C13 C8 S2 121.1(5) . .
C8 C9 H9 120.1 . .
C8 C9 C10 119.8(6) . .
C10 C9 H9 120.1 . .
C9 C10 H10 120.4 . .
C11 C10 C9 119.1(6) . .
C11 C10 H10 120.4 . .
C10 C11 C12 121.2(6) . .
C10 C11 Br2 119.6(5) . .
C12 C11 Br2 119.2(5) . .
C11 C12 H12 120.1 . .
C11 C12 C13 119.7(7) . .
C13 C12 H12 120.1 . .
C8 C13 C12 119.7(6) . .
C8 C13 H13 120.1 . .
C12 C13 H13 120.1 . .
C1 S1 Cu1 98.8(2) 5_666 .
C2 S1 C1 103.1(3) . 5_666
C2 S1 Cu1 110.1(2) . .
C1 S2 Cu2 98.0(2) . .
C8 S2 C1 102.3(3) . .
C8 S2 Cu2 110.6(2) . .
S1 Cu1 Cu1 156.74(4) . 2_655
S1 Cu1 Cu2 133.84(6) . 2_655
S1 Cu1 Cu2 139.26(5) . .
S1 Cu1 I1 112.64(5) . .
S1 Cu1 I1 111.47(5) . 2_655
S1 Cu1 I2 94.73(5) . .
Cu1 Cu1 Cu2 58.57(3) 2_655 .
Cu1 Cu1 Cu2 64.28(3) 2_655 2_655
Cu1 Cu1 I1 59.54(3) 2_655 .
Cu1 Cu1 I2 108.483(19) 2_655 .
Cu2 Cu1 Cu2 59.47(4) 2_655 .
Cu2 Cu1 I2 57.64(3) 2_655 .
I1 Cu1 Cu1 60.80(3) 2_655 2_655
I1 Cu1 Cu2 107.41(3) 2_655 .
I1 Cu1 Cu2 58.55(3) . .
I1 Cu1 Cu2 60.85(3) 2_655 2_655
I1 Cu1 Cu2 110.94(4) . 2_655
I1 Cu1 I1 114.83(3) 2_655 .
I1 Cu1 I2 113.86(3) 2_655 .
I1 Cu1 I2 107.59(3) . .
I2 Cu1 Cu2 57.84(3) . .
S2 Cu2 Cu1 139.73(5) . .
S2 Cu2 Cu1 140.88(6) . 2_655
S2 Cu2 Cu2 152.72(4) . 2_655
S2 Cu2 I1 98.00(5) . .
S2 Cu2 I2 108.26(5) . .
S2 Cu2 I2 112.97(5) . 2_655
Cu1 Cu2 Cu1 57.15(4) 2_655 .
Cu1 Cu2 Cu2 62.98(3) 2_655 2_655
Cu1 Cu2 I1 58.75(3) 2_655 .
Cu1 Cu2 I2 108.99(3) 2_655 .
Cu2 Cu2 Cu1 57.54(3) 2_655 .
I1 Cu2 Cu1 57.74(3) . .
I1 Cu2 Cu2 108.53(2) . 2_655
I1 Cu2 I2 108.59(3) . .
I2 Cu2 Cu1 106.91(3) 2_655 .
I2 Cu2 Cu1 62.77(3) 2_655 2_655
I2 Cu2 Cu1 59.84(3) . .
I2 Cu2 Cu2 60.57(3) 2_655 2_655
I2 Cu2 Cu2 57.68(3) . 2_655
I2 Cu2 I1 116.62(3) 2_655 .
I2 Cu2 I2 111.43(3) 2_655 .
Cu1 I1 Cu1 59.66(3) 2_655 .
Cu1 I1 Cu2 63.72(3) . .
Cu1 I1 Cu2 60.39(3) 2_655 .
Cu2 I2 Cu1 59.60(3) 2_655 .
Cu2 I2 Cu1 62.32(3) . .
Cu2 I2 Cu2 61.75(3) 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 1.803(6) 5_666
C1 S2 1.827(6) .
C2 C3 1.385(9) .
C2 C7 1.387(9) .
C2 S1 1.788(7) .
C3 H3 0.9500 .
C3 C4 1.387(10) .
C4 H4 0.9500 .
C4 C5 1.381(11) .
C5 C6 1.385(10) .
C5 Br1 1.898(7) .
C6 H6 0.9500 .
C6 C7 1.382(10) .
C7 H7 0.9500 .
C8 C9 1.390(9) .
C8 C13 1.387(9) .
C8 S2 1.782(6) .
C9 H9 0.9500 .
C9 C10 1.400(9) .
C10 H10 0.9500 .
C10 C11 1.380(10) .
C11 C12 1.385(10) .
C11 Br2 1.891(6) .
C12 H12 0.9500 .
C12 C13 1.389(10) .
C13 H13 0.9500 .
S1 C1 1.803(6) 5_666
S1 Cu1 2.3170(17) .
S2 Cu2 2.3239(17) .
Cu1 Cu1 2.6427(16) 2_655
Cu1 Cu2 2.8341(12) .
Cu1 Cu2 2.6841(11) 2_655
Cu1 I1 2.6728(10) .
Cu1 I1 2.6395(9) 2_655
Cu1 I2 2.7670(10) .
Cu2 Cu1 2.6841(11) 2_655
Cu2 Cu2 2.7402(16) 2_655
Cu2 I1 2.6964(9) .
Cu2 I2 2.7092(9) .
Cu2 I2 2.6288(9) 2_655
I1 Cu1 2.6394(9) 2_655
I2 Cu2 2.6288(9) 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 -0.4(11) . .
C3 C2 C7 C6 2.6(10) . .
C3 C2 S1 C1 -136.5(5) . 5_666
C3 C2 S1 Cu1 118.9(5) . .
C3 C4 C5 C6 0.7(11) . .
C3 C4 C5 Br1 -178.8(5) . .
C4 C5 C6 C7 0.7(11) . .
C5 C6 C7 C2 -2.3(11) . .
C7 C2 C3 C4 -1.3(10) . .
C7 C2 S1 C1 44.3(6) . 5_666
C7 C2 S1 Cu1 -60.3(6) . .
C8 C9 C10 C11 1.2(10) . .
C9 C8 C13 C12 2.7(10) . .
C9 C8 S2 C1 -99.9(5) . .
C9 C8 S2 Cu2 156.6(4) . .
C9 C10 C11 C12 1.0(10) . .
C9 C10 C11 Br2 -178.1(5) . .
C10 C11 C12 C13 -1.4(10) . .
C11 C12 C13 C8 -0.5(10) . .
C13 C8 C9 C10 -3.1(10) . .
C13 C8 S2 C1 81.8(6) . .
C13 C8 S2 Cu2 -21.8(6) . .
S1 C1 S2 C8 78.3(4) 5_666 .
S1 C1 S2 Cu2 -168.4(3) 5_666 .
S1 C2 C3 C4 179.5(5) . .
S1 C2 C7 C6 -178.2(5) . .
S2 C8 C9 C10 178.5(5) . .
S2 C8 C13 C12 -179.0(5) . .
Br1 C5 C6 C7 -179.8(5) . .
Br2 C11 C12 C13 177.7(5) . .
