#------------------------------------------------------------------------------
#$Date: 2016-03-24 14:32:51 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179667 $
#$URL: svn://www.crystallography.net/cod/cif/4/51/20/4512088.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_4512088
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                 123.3990(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   20.6176(10)
_cell_length_b                   13.5558(7)
_cell_length_c                   15.5707(7)
_cell_measurement_reflns_used    9649
_cell_measurement_temperature    115
_cell_measurement_theta_max      27.4834
_cell_measurement_theta_min      2.3665
_cell_volume                     3633.2(3)
_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      115.0
_diffrn_detector                 'CCD Plate'
_diffrn_detector_area_resol_mean 9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.987
_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  0.0240
_diffrn_reflns_av_unetI/netI     0.0222
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.987
_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       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            17144
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.580
_diffrn_reflns_theta_min         2.018
_diffrn_source                   'X-ray tube'
_diffrn_source_target            Mo
_diffrn_source_type              'Siemens KFF Mo 2K-180'
_exptl_absorpt_coefficient_mu    10.358
_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    2.819
_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         3.288
_refine_diff_density_min         -0.869
_refine_diff_density_rms         0.228
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.284
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         4151
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.284
_refine_ls_R_factor_all          0.0360
_refine_ls_R_factor_gt           0.0322
_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)+(0.0211P)²+114.0069P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0930
_refine_ls_wR_factor_ref         0.0943
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3813
_reflns_number_total             4151
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            cg500905z_si_002.cif
_cod_data_source_block           13mk0603_115k_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               4512088
#BEGIN Tags that were not found in dictionaries:
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  H3 of C3, H4 of C4, H6 of C6, H7 of C7, H9 of C9, H10 of C10, H12 of C12,
  H13 of C13, {H1A,H1B} of C1
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
I1 I 0.59212(3) 0.62565(3) 0.41866(3) 0.01177(11) Uani 1 1 d . .
I2 I 0.41579(2) 0.39206(3) 0.29529(3) 0.00976(11) Uani 1 1 d . .
Br1 Br 0.36358(5) 1.12692(5) 0.28954(7) 0.02243(18) Uani 1 1 d . .
Br2 Br 0.64422(5) -0.11101(5) 0.45615(7) 0.02285(18) Uani 1 1 d . .
Cu1 Cu 0.44519(5) 0.58499(7) 0.26907(7) 0.01381(18) Uani 1 1 d . .
Cu2 Cu 0.56148(5) 0.43788(6) 0.35025(7) 0.01256(18) Uani 1 1 d . .
S1 S 0.35663(10) 0.65243(12) 0.29969(12) 0.0105(3) Uani 1 1 d . .
S2 S 0.64863(9) 0.36066(12) 0.50566(13) 0.0094(3) Uani 1 1 d . .
C1 C 0.5933(4) 0.3750(5) 0.5646(5) 0.0131(13) Uani 1 1 d . .
H1A H 0.5745 0.4440 0.5540 0.016 Uiso 1 1 calc R U
H1B H 0.5469 0.3320 0.5274 0.016 Uiso 1 1 calc R U
C2 C 0.3602(4) 0.7840(5) 0.2974(5) 0.0116(13) Uani 1 1 d . .
C3 C 0.2937(4) 0.8339(5) 0.2237(6) 0.0175(15) Uani 1 1 d . .
H3 H 0.2480 0.7982 0.1761 0.021 Uiso 1 1 calc R U
C4 C 0.2942(4) 0.9365(6) 0.2197(6) 0.0176(15) Uani 1 1 d . .
H4 H 0.2492 0.9712 0.1689 0.021 Uiso 1 1 calc R U
C5 C 0.3608(4) 0.9872(5) 0.2903(6) 0.0155(14) Uani 1 1 d . .
C6 C 0.4275(4) 0.9375(5) 0.3632(6) 0.0171(15) Uani 1 1 d . .
H6 H 0.4730 0.9735 0.4112 0.020 Uiso 1 1 calc R U
C7 C 0.4281(4) 0.8354(5) 0.3662(6) 0.0166(14) Uani 1 1 d . .
H7 H 0.4742 0.8008 0.4146 0.020 Uiso 1 1 calc R U
C8 C 0.6472(4) 0.2305(5) 0.4892(5) 0.0109(13) Uani 1 1 d . .
C9 C 0.7113(4) 0.1755(5) 0.5603(6) 0.0142(14) Uani 1 1 d . .
H9 H 0.7556 0.2077 0.6159 0.017 Uiso 1 1 calc R U
C10 C 0.7115(4) 0.0730(5) 0.5509(6) 0.0170(15) Uani 1 1 d . .
H10 H 0.7551 0.0350 0.6001 0.020 Uiso 1 1 calc R U
C11 C 0.6466(4) 0.0279(5) 0.4680(6) 0.0145(14) Uani 1 1 d . .
C12 C 0.5830(4) 0.0826(5) 0.3948(5) 0.0154(14) Uani 1 1 d . .
H12 H 0.5397 0.0506 0.3377 0.018 Uiso 1 1 calc R U
C13 C 0.5830(4) 0.1843(5) 0.4054(5) 0.0150(14) Uani 1 1 d . .
H13 H 0.5395 0.2222 0.3558 0.018 Uiso 1 1 calc R U
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
Cu1 I1 Cu1 59.47(3) 2_655 .
Cu1 I1 Cu2 63.53(3) . .
Cu1 I1 Cu2 60.21(3) 2_655 .
Cu2 I2 Cu1 62.21(3) . .
Cu2 I2 Cu1 59.44(3) 2_655 .
Cu2 I2 Cu2 61.60(3) 2_655 .
I1 Cu1 I1 114.95(3) 2_655 .
I1 Cu1 I2 114.03(3) 2_655 .
I1 Cu1 I2 107.57(3) . .
I1 Cu1 Cu2 60.96(3) 2_655 2_655
I1 Cu1 Cu2 111.05(4) . 2_655
I1 Cu1 Cu2 107.52(3) 2_655 .
I1 Cu1 Cu2 58.67(3) . .
I2 Cu1 Cu2 57.83(3) . .
Cu1 Cu1 I1 60.88(3) 2_655 2_655
Cu1 Cu1 I1 59.65(3) 2_655 .
Cu1 Cu1 I2 108.56(2) 2_655 .
Cu1 Cu1 Cu2 64.29(3) 2_655 2_655
Cu1 Cu1 Cu2 58.59(3) 2_655 .
Cu2 Cu1 I2 57.74(3) 2_655 .
Cu2 Cu1 Cu2 59.44(4) 2_655 .
S1 Cu1 I1 112.54(5) . .
S1 Cu1 I1 111.33(5) . 2_655
S1 Cu1 I2 94.66(5) . .
S1 Cu1 Cu1 156.73(5) . 2_655
S1 Cu1 Cu2 139.29(6) . .
S1 Cu1 Cu2 133.82(6) . 2_655
I1 Cu2 I2 108.64(3) . .
I1 Cu2 Cu1 57.80(3) . .
I1 Cu2 Cu2 108.64(2) . 2_655
I2 Cu2 I1 116.71(3) 2_655 .
I2 Cu2 I2 111.53(3) 2_655 .
I2 Cu2 Cu1 106.93(3) 2_655 .
I2 Cu2 Cu1 62.82(3) 2_655 2_655
I2 Cu2 Cu1 59.96(3) . .
I2 Cu2 Cu2 60.56(3) 2_655 2_655
I2 Cu2 Cu2 57.84(3) . 2_655
Cu1 Cu2 I1 58.83(3) 2_655 .
Cu1 Cu2 I2 109.13(4) 2_655 .
Cu1 Cu2 Cu1 57.12(4) 2_655 .
Cu1 Cu2 Cu2 63.00(3) 2_655 2_655
Cu2 Cu2 Cu1 57.56(3) 2_655 .
S2 Cu2 I1 97.77(5) . .
S2 Cu2 I2 112.89(5) . 2_655
S2 Cu2 I2 108.28(5) . .
S2 Cu2 Cu1 139.77(6) . .
S2 Cu2 Cu1 140.69(6) . 2_655
S2 Cu2 Cu2 152.87(5) . 2_655
C1 S1 Cu1 98.7(2) 5_666 .
C2 S1 Cu1 110.2(2) . .
C2 S1 C1 103.0(3) . 5_666
C1 S2 Cu2 97.9(2) . .
C8 S2 Cu2 110.8(2) . .
C8 S2 C1 102.3(3) . .
S1 C1 S2 116.9(4) 5_666 .
S1 C1 H1A 108.1 5_666 .
S1 C1 H1B 108.1 5_666 .
S2 C1 H1A 108.1 . .
S2 C1 H1B 108.1 . .
H1A C1 H1B 107.3 . .
C3 C2 S1 118.1(5) . .
C3 C2 C7 120.7(7) . .
C7 C2 S1 121.2(5) . .
C2 C3 H3 120.2 . .
C2 C3 C4 119.7(7) . .
C4 C3 H3 120.2 . .
C3 C4 H4 120.3 . .
C5 C4 C3 119.5(7) . .
C5 C4 H4 120.3 . .
C4 C5 Br1 120.9(6) . .
C4 C5 C6 120.9(7) . .
C6 C5 Br1 118.1(6) . .
C5 C6 H6 120.0 . .
C5 C6 C7 120.0(7) . .
C7 C6 H6 120.0 . .
C2 C7 H7 120.4 . .
C6 C7 C2 119.2(7) . .
C6 C7 H7 120.4 . .
C9 C8 S2 119.1(5) . .
C9 C8 C13 120.1(6) . .
C13 C8 S2 120.8(5) . .
C8 C9 H9 119.7 . .
C8 C9 C10 120.6(7) . .
C10 C9 H9 119.7 . .
C9 C10 H10 120.7 . .
C11 C10 C9 118.6(7) . .
C11 C10 H10 120.7 . .
C10 C11 Br2 119.3(5) . .
C12 C11 Br2 119.4(5) . .
C12 C11 C10 121.3(7) . .
C11 C12 H12 120.1 . .
C11 C12 C13 119.7(7) . .
C13 C12 H12 120.1 . .
C8 C13 H13 120.2 . .
C12 C13 C8 119.7(7) . .
C12 C13 H13 120.2 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
I1 Cu1 2.6716(10) .
I1 Cu1 2.6391(10) 2_655
I1 Cu2 2.6966(10) .
I2 Cu1 2.7652(10) .
I2 Cu2 2.7039(10) .
I2 Cu2 2.6286(9) 2_655
Br1 C5 1.895(7) .
Br2 C11 1.890(7) .
Cu1 I1 2.6391(10) 2_655
Cu1 Cu1 2.6340(17) 2_655
Cu1 Cu2 2.8260(12) .
Cu1 Cu2 2.6768(12) 2_655
Cu1 S1 2.3143(18) .
Cu2 I2 2.6286(9) 2_655
Cu2 Cu1 2.6768(12) 2_655
Cu2 Cu2 2.7312(17) 2_655
Cu2 S2 2.3223(18) .
S1 C1 1.807(7) 5_666
S1 C2 1.787(7) .
S2 C1 1.827(7) .
S2 C8 1.780(7) .
C1 S1 1.807(7) 5_666
C1 H1A 0.9900 .
C1 H1B 0.9900 .
C2 C3 1.386(10) .
C2 C7 1.393(10) .
C3 H3 0.9500 .
C3 C4 1.392(10) .
C4 H4 0.9500 .
C4 C5 1.380(11) .
C5 C6 1.384(10) .
C6 H6 0.9500 .
C6 C7 1.385(10) .
C7 H7 0.9500 .
C8 C9 1.385(10) .
C8 C13 1.395(10) .
C9 H9 0.9500 .
C9 C10 1.398(10) .
C10 H10 0.9500 .
C10 C11 1.389(11) .
C11 C12 1.386(10) .
C12 H12 0.9500 .
C12 C13 1.388(10) .
C13 H13 0.9500 .
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
Br1 C5 C6 C7 -179.8(6) . .
Br2 C11 C12 C13 177.3(6) . .
Cu1 S1 C2 C3 118.3(5) . .
Cu1 S1 C2 C7 -60.5(6) . .
Cu2 S2 C1 S1 -168.5(3) . 5_666
Cu2 S2 C8 C9 157.2(5) . .
Cu2 S2 C8 C13 -21.9(6) . .
S1 C2 C3 C4 179.9(6) . .
S1 C2 C7 C6 -178.4(6) . .
S2 C8 C9 C10 178.7(5) . .
S2 C8 C13 C12 -179.4(6) . .
C1 S1 C2 C3 -137.2(6) 5_666 .
C1 S1 C2 C7 44.0(6) 5_666 .
C1 S2 C8 C9 -99.3(6) . .
C1 S2 C8 C13 81.5(6) . .
C2 C3 C4 C5 -0.8(11) . .
C3 C2 C7 C6 2.9(11) . .
C3 C4 C5 Br1 -178.8(6) . .
C3 C4 C5 C6 1.6(11) . .
C4 C5 C6 C7 -0.1(11) . .
C5 C6 C7 C2 -2.1(11) . .
C7 C2 C3 C4 -1.4(11) . .
C8 S2 C1 S1 78.2(5) . 5_666
C8 C9 C10 C11 1.0(11) . .
C9 C8 C13 C12 1.5(11) . .
C9 C10 C11 Br2 -178.0(5) . .
C9 C10 C11 C12 1.0(11) . .
C10 C11 C12 C13 -1.7(11) . .
C11 C12 C13 C8 0.4(11) . .
C13 C8 C9 C10 -2.2(10) . .
