#------------------------------------------------------------------------------
#$Date: 2016-03-24 14:32:51 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179667 $
#$URL: svn://www.crystallography.net/cod/cif/4/51/20/4512083.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_4512083
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         'C17 H19 Br Cu N S2'
_chemical_formula_sum            'C17 H19 Br Cu N S2'
_chemical_formula_weight         444.90
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2012-12-04
_audit_creation_method
;
  Olex2 1.2
  (compiled 2012.11.06 svn.r2526, GUI svn.r4372)
;
_audit_update_record
;
2012-12-04 # Formatted by publCIF
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   13.6576(4)
_cell_length_b                   16.2552(5)
_cell_length_c                   16.3334(5)
_cell_measurement_reflns_used    9847
_cell_measurement_temperature    115(2)
_cell_measurement_theta_max      30.4772
_cell_measurement_theta_min      2.3126
_cell_volume                     3626.13(19)
_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(2)
_diffrn_detector                 'CCD Plate'
_diffrn_detector_area_resol_mean 9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.998
_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  0.0400
_diffrn_reflns_av_unetI/netI     0.0169
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            76562
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.695
_diffrn_reflns_theta_min         2.799
_diffrn_source                   'X-ray tube'
_diffrn_source_target            Mo
_diffrn_source_type              'Siemens KFF Mo 2K-180'
_exptl_absorpt_coefficient_mu    3.634
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.5957
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_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    1.630
_exptl_crystal_description       prism
_exptl_crystal_F_000             1792
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.440
_refine_diff_density_min         -0.353
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         5611
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0278
_refine_ls_R_factor_gt           0.0200
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[σ²(Fo²)+(0.0224P)²+1.6325P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0460
_refine_ls_wR_factor_ref         0.0483
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4821
_reflns_number_total             5611
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            cg500905z_si_003.cif
_cod_data_source_block           12mk2811_compound_13
_cod_depositor_comments
'Adding full bibliography for 4512075--4512092.cif.'
_cod_database_code               4512083
#BEGIN Tags that were not found in dictionaries:
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  H16 of C16, H15 of C15, {H11A,H11B} of C11, H9 of C9, H8 of C8, H7 of C7,
  H6 of C6, H13 of C13, H14 of C14
 At 1.5 times of:
  {H18A,H18B,H18C} of C18, {H3A,H3B,H3C} of C3, {H10A,H10B,H10C} of C10
2.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C8(H8), C9(H9), C13(H13), C14(H14), C15(H15), C16(H16)
2.c Idealised Me refined as rotating group:
 C3(H3A,H3B,H3C), C10(H10A,H10B,H10C), C18(H18A,H18B,H18C)
;
#END Tags that were not found in dictionaries
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'
'-x, -y, -z'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'
'x-1/2, y, -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
Cu1 Cu 0.03247(2) 1.00419(2) 0.41023(2) 0.01885(4) Uani 1 1 d . .
Br1 Br 0.12126(2) 0.94022(2) 0.53687(2) 0.01643(4) Uani 1 1 d . .
S1 S 0.00420(2) 0.87725(2) 0.35145(2) 0.01338(6) Uani 1 1 d . .
S2 S -0.11237(2) 0.72803(2) 0.40658(2) 0.01615(6) Uani 1 1 d . .
N1 N 0.12277(9) 1.08167(7) 0.35877(7) 0.0196(2) Uani 1 1 d . .
C2 C 0.18392(10) 1.11614(9) 0.32583(9) 0.0200(3) Uani 1 1 d . .
C3 C 0.26292(11) 1.15764(10) 0.28256(10) 0.0262(3) Uani 1 1 d . .
H3A H 0.2361 1.2035 0.2507 0.039 Uiso 1 1 calc R U
H3B H 0.2953 1.1187 0.2456 0.039 Uiso 1 1 calc R U
H3C H 0.3106 1.1787 0.3222 0.039 Uiso 1 1 calc R U
C4 C -0.07434(9) 0.87290(8) 0.26401(7) 0.0140(2) Uani 1 1 d . .
C5 C -0.05050(10) 0.82031(8) 0.19916(8) 0.0175(3) Uani 1 1 d . .
C6 C -0.11684(12) 0.81576(9) 0.13414(9) 0.0231(3) Uani 1 1 d . .
H6 H -0.1017 0.7818 0.0885 0.028 Uiso 1 1 calc R U
C7 C -0.20375(12) 0.85927(9) 0.13425(10) 0.0265(3) Uani 1 1 d . .
H7 H -0.2480 0.8540 0.0897 0.032 Uiso 1 1 calc R U
C8 C -0.22630(11) 0.91060(9) 0.19946(10) 0.0260(3) Uani 1 1 d . .
H8 H -0.2862 0.9403 0.1999 0.031 Uiso 1 1 calc R U
C9 C -0.16093(11) 0.91834(8) 0.26395(9) 0.0204(3) Uani 1 1 d . .
H9 H -0.1751 0.9546 0.3080 0.025 Uiso 1 1 calc R U
C10 C 0.04068(11) 0.76848(10) 0.19906(9) 0.0268(3) Uani 1 1 d . .
H10A H 0.0984 0.8043 0.2006 0.040 Uiso 1 1 calc R U
H10B H 0.0424 0.7348 0.1493 0.040 Uiso 1 1 calc R U
H10C H 0.0407 0.7326 0.2472 0.040 Uiso 1 1 calc R U
C11 C -0.07991(9) 0.83321(8) 0.42612(8) 0.0148(2) Uani 1 1 d . .
H11A H -0.0496 0.8368 0.4811 0.018 Uiso 1 1 calc R U
H11B H -0.1404 0.8667 0.4270 0.018 Uiso 1 1 calc R U
C12 C -0.00358(10) 0.67385(8) 0.43091(8) 0.0157(2) Uani 1 1 d . .
C13 C 0.07582(10) 0.71025(9) 0.46990(9) 0.0219(3) Uani 1 1 d . .
H13 H 0.0744 0.7673 0.4825 0.026 Uiso 1 1 calc R U
C14 C 0.15730(11) 0.66328(11) 0.49044(10) 0.0305(3) Uani 1 1 d . .
H14 H 0.2115 0.6883 0.5171 0.037 Uiso 1 1 calc R U
C15 C 0.15964(12) 0.58018(11) 0.47219(11) 0.0335(4) Uani 1 1 d . .
H15 H 0.2150 0.5479 0.4867 0.040 Uiso 1 1 calc R U
C16 C 0.08055(13) 0.54446(10) 0.43262(10) 0.0290(3) Uani 1 1 d . .
H16 H 0.0828 0.4875 0.4199 0.035 Uiso 1 1 calc R U
C17 C -0.00191(11) 0.58970(9) 0.41107(8) 0.0211(3) Uani 1 1 d . .
C18 C -0.08644(14) 0.54913(9) 0.36776(10) 0.0306(3) Uani 1 1 d . .
H18A H -0.1474 0.5617 0.3968 0.046 Uiso 1 1 calc R U
H18B H -0.0763 0.4894 0.3668 0.046 Uiso 1 1 calc R U
H18C H -0.0905 0.5699 0.3115 0.046 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'
N N 0.0061 0.0033 '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
Br1 Cu1 Br1 105.429(7) 5_576 .
S1 Cu1 Br1 109.508(11) . 5_576
S1 Cu1 Br1 92.935(10) . .
N1 Cu1 Br1 107.71(4) . .
N1 Cu1 Br1 117.15(4) . 5_576
N1 Cu1 S1 120.20(4) . .
Cu1 Br1 Cu1 74.572(7) 5_576 .
C4 S1 Cu1 117.91(4) . .
C4 S1 C11 98.10(6) . .
C11 S1 Cu1 100.26(4) . .
C12 S2 C11 103.09(6) . .
C2 N1 Cu1 169.20(12) . .
N1 C2 C3 178.15(16) . .
C2 C3 H3A 109.5 . .
C2 C3 H3B 109.5 . .
C2 C3 H3C 109.5 . .
H3A C3 H3B 109.5 . .
H3A C3 H3C 109.5 . .
H3B C3 H3C 109.5 . .
C5 C4 S1 119.29(10) . .
C9 C4 S1 119.25(10) . .
C9 C4 C5 121.36(12) . .
C4 C5 C10 122.40(12) . .
C6 C5 C4 117.16(13) . .
C6 C5 C10 120.42(13) . .
C5 C6 H6 119.0 . .
C7 C6 C5 121.92(14) . .
C7 C6 H6 119.0 . .
C6 C7 H7 120.0 . .
C6 C7 C8 119.96(13) . .
C8 C7 H7 120.0 . .
C7 C8 H8 120.2 . .
C9 C8 C7 119.66(14) . .
C9 C8 H8 120.2 . .
C4 C9 H9 120.0 . .
C8 C9 C4 119.91(14) . .
C8 C9 H9 120.0 . .
C5 C10 H10A 109.5 . .
C5 C10 H10B 109.5 . .
C5 C10 H10C 109.5 . .
H10A C10 H10B 109.5 . .
H10A C10 H10C 109.5 . .
H10B C10 H10C 109.5 . .
S1 C11 H11A 108.7 . .
S1 C11 H11B 108.7 . .
S2 C11 S1 114.26(7) . .
S2 C11 H11A 108.7 . .
S2 C11 H11B 108.7 . .
H11A C11 H11B 107.6 . .
C13 C12 S2 123.05(10) . .
C13 C12 C17 120.47(13) . .
C17 C12 S2 116.45(11) . .
C12 C13 H13 120.0 . .
C12 C13 C14 120.08(14) . .
C14 C13 H13 120.0 . .
C13 C14 H14 119.9 . .
C15 C14 C13 120.17(16) . .
C15 C14 H14 119.9 . .
C14 C15 H15 120.3 . .
C14 C15 C16 119.43(15) . .
C16 C15 H15 120.3 . .
C15 C16 H16 119.1 . .
C15 C16 C17 121.85(15) . .
C17 C16 H16 119.1 . .
C12 C17 C18 121.46(14) . .
C16 C17 C12 117.99(15) . .
C16 C17 C18 120.55(14) . .
C17 C18 H18A 109.5 . .
C17 C18 H18B 109.5 . .
C17 C18 H18C 109.5 . .
H18A C18 H18B 109.5 . .
H18A C18 H18C 109.5 . .
H18B C18 H18C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cu1 Br1 2.6135(2) .
Cu1 Br1 2.4436(2) 5_576
Cu1 S1 2.3083(4) .
Cu1 N1 1.9528(12) .
Br1 Cu1 2.4436(2) 5_576
S1 C4 1.7875(13) .
S1 C11 1.8221(13) .
S2 C11 1.7949(13) .
S2 C12 1.7723(13) .
N1 C2 1.1407(18) .
C2 C3 1.456(2) .
C3 H3A 0.9800 .
C3 H3B 0.9800 .
C3 H3C 0.9800 .
C4 C5 1.3995(18) .
C4 C9 1.3943(19) .
C5 C6 1.3980(19) .
C5 C10 1.504(2) .
C6 H6 0.9500 .
C6 C7 1.382(2) .
C7 H7 0.9500 .
C7 C8 1.388(2) .
C8 H8 0.9500 .
C8 C9 1.387(2) .
C9 H9 0.9500 .
C10 H10A 0.9800 .
C10 H10B 0.9800 .
C10 H10C 0.9800 .
C11 H11A 0.9900 .
C11 H11B 0.9900 .
C12 C13 1.390(2) .
C12 C17 1.4060(19) .
C13 H13 0.9500 .
C13 C14 1.391(2) .
C14 H14 0.9500 .
C14 C15 1.384(3) .
C15 H15 0.9500 .
C15 C16 1.386(3) .
C16 H16 0.9500 .
C16 C17 1.390(2) .
C17 C18 1.506(2) .
C18 H18A 0.9800 .
C18 H18B 0.9800 .
C18 H18C 0.9800 .
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
Cu1 S1 C4 C5 140.29(9)
Cu1 S1 C4 C9 -43.41(12)
Cu1 S1 C11 S2 -174.89(6)
S1 C4 C5 C6 176.66(10)
S1 C4 C5 C10 -1.64(18)
S1 C4 C9 C8 -174.92(11)
S2 C12 C13 C14 177.16(12)
S2 C12 C17 C16 -177.16(11)
S2 C12 C17 C18 2.86(18)
C4 S1 C11 S2 64.69(8)
C4 C5 C6 C7 -1.8(2)
C5 C4 C9 C8 1.3(2)
C5 C6 C7 C8 1.3(2)
C6 C7 C8 C9 0.5(2)
C7 C8 C9 C4 -1.8(2)
C9 C4 C5 C6 0.44(19)
C9 C4 C5 C10 -177.86(14)
C10 C5 C6 C7 176.57(14)
C11 S1 C4 C5 -113.51(11)
C11 S1 C4 C9 62.79(12)
C11 S2 C12 C13 10.35(13)
C11 S2 C12 C17 -171.69(10)
C12 S2 C11 S1 71.87(8)
C12 C13 C14 C15 0.0(2)
C13 C12 C17 C16 0.9(2)
C13 C12 C17 C18 -179.12(13)
C13 C14 C15 C16 0.6(2)
C14 C15 C16 C17 -0.5(2)
C15 C16 C17 C12 -0.3(2)
C15 C16 C17 C18 179.72(15)
C17 C12 C13 C14 -0.7(2)
