#------------------------------------------------------------------------------
#$Date: 2016-03-25 16:28:59 +0200 (Fri, 25 Mar 2016) $
#$Revision: 179972 $
#$URL: svn://www.crystallography.net/cod/cif/7/02/66/7026640.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_7026640
loop_
_publ_author_name
'Belén Lago, Ana'
'Amoedo, Almudena'
'Carballo, Rosa'
'García-Martínez, Emilia'
'Vázquez-López, Ezequiel M'
_publ_section_title
;
 Metal coordination and in situ S-C bond cleavage of the
 bis(2-pyridylthio)methane ligand.
;
_journal_issue                   42
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              10076
_journal_page_last               10087
_journal_paper_doi               10.1039/c0dt00560f
_journal_volume                  39
_journal_year                    2010
_chemical_formula_sum            'C13 H13 Br2 Cu N3 S2'
_chemical_formula_weight         498.74
_chemical_name_systematic
;
?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 99.709(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.8365(17)
_cell_length_b                   12.617(3)
_cell_length_c                   15.658(3)
_cell_measurement_temperature    293(2)
_cell_volume                     1720.7(6)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'ORTEPIII and PLATON'
_computing_publication_material  'Bruker SHELX97'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.930
_diffrn_measured_fraction_theta_max 0.930
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0642
_diffrn_reflns_av_sigmaI/netI    0.1312
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            9780
_diffrn_reflns_theta_full        28.03
_diffrn_reflns_theta_max         28.03
_diffrn_reflns_theta_min         2.08
_exptl_absorpt_coefficient_mu    6.151
_exptl_absorpt_correction_T_max  1.000000
_exptl_absorpt_correction_T_min  0.578853
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            'dark green'
_exptl_crystal_density_diffrn    1.925
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             972
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.514
_refine_diff_density_min         -0.600
_refine_diff_density_rms         0.102
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.760
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         3888
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.760
_refine_ls_R_factor_all          0.1162
_refine_ls_R_factor_gt           0.0403
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0196P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0621
_refine_ls_wR_factor_ref         0.0730
_reflns_number_gt                1917
_reflns_number_total             3888
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c0dt00560f.txt
_cod_data_source_block           6
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_cell_volume        1720.6(6)
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               7026640
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
Cu Cu 0.29796(7) 0.84989(5) 0.21331(4) 0.03162(17) Uani 1 1 d .
Br1 Br 0.13611(6) 0.89261(5) 0.07846(4) 0.04398(18) Uani 1 1 d .
Br2 Br 0.45600(6) 0.90740(5) 0.34558(4) 0.04566(18) Uani 1 1 d .
C1 C 0.6241(6) 1.1243(4) 0.1152(3) 0.0381(14) Uani 1 1 d .
H1A H 0.5838 1.1947 0.1007 0.046 Uiso 1 1 calc R
H1B H 0.6820 1.1021 0.0709 0.046 Uiso 1 1 calc R
S1 S 0.46911(16) 1.03356(11) 0.11926(9) 0.0393(4) Uani 1 1 d .
N1 N 0.4849(4) 0.8294(3) 0.1575(2) 0.0318(11) Uani 1 1 d .
C2 C 0.5591(5) 0.9078(4) 0.1236(3) 0.0280(12) Uani 1 1 d .
C3 C 0.6941(6) 0.8871(4) 0.0917(3) 0.0363(14) Uani 1 1 d .
H3 H 0.7465 0.9417 0.0695 0.044 Uiso 1 1 calc R
C4 C 0.7491(6) 0.7847(5) 0.0935(3) 0.0457(16) Uani 1 1 d .
H4 H 0.8386 0.7697 0.0719 0.055 Uiso 1 1 calc R
C5 C 0.6714(6) 0.7055(4) 0.1272(3) 0.0430(15) Uani 1 1 d .
H5 H 0.7071 0.6360 0.1286 0.052 Uiso 1 1 calc R
C6 C 0.5417(6) 0.7298(4) 0.1583(3) 0.0388(14) Uani 1 1 d .
H6 H 0.4895 0.6756 0.1812 0.047 Uiso 1 1 calc R
S11 S 0.74847(16) 1.12638(11) 0.22007(9) 0.0368(4) Uani 1 1 d .
N11 N 0.8832(4) 1.3147(3) 0.2296(2) 0.0305(11) Uani 1 1 d .
C12 C 0.8945(6) 1.2150(4) 0.2005(3) 0.0287(12) Uani 1 1 d .
C13 C 1.0130(6) 1.1836(5) 0.1580(3) 0.0436(15) Uani 1 1 d .
H13 H 1.0156 1.1153 0.1360 0.052 Uiso 1 1 calc R
C14 C 1.1257(6) 1.2552(5) 0.1492(3) 0.0458(16) Uani 1 1 d .
H14 H 1.2073 1.2351 0.1222 0.055 Uiso 1 1 calc R
C15 C 1.1188(6) 1.3569(5) 0.1802(3) 0.0417(15) Uani 1 1 d .
H15 H 1.1950 1.4060 0.1746 0.050 Uiso 1 1 calc R
C16 C 0.9957(6) 1.3841(4) 0.2198(3) 0.0416(15) Uani 1 1 d .
H16 H 0.9900 1.4528 0.2405 0.050 Uiso 1 1 calc R
N111 N -0.0003(6) 0.5959(4) 0.0961(4) 0.0698(17) Uani 1 1 d .
C111 C 0.0991(8) 0.5990(5) 0.0594(4) 0.0498(16) Uani 1 1 d .
C112 C 0.2277(7) 0.6007(5) 0.0121(4) 0.072(2) Uani 1 1 d .
H11A H 0.3078 0.5553 0.0405 0.108 Uiso 1 1 calc R
H11B H 0.2659 0.6718 0.0107 0.108 Uiso 1 1 calc R
H11C H 0.1940 0.5762 -0.0460 0.108 Uiso 1 1 calc R
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'
N N 0.0061 0.0033 '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'
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
N11 Cu N1 159.83(17) 2_645 .
N11 Cu Br1 92.29(12) 2_645 .
N1 Cu Br1 93.33(12) . .
N11 Cu Br2 94.23(11) 2_645 .
N1 Cu Br2 90.71(11) . .
Br1 Cu Br2 149.49(3) . .
N11 Cu S11 58.79(12) 2_645 2_645
N1 Cu S11 101.37(13) . 2_645
Br1 Cu S11 114.35(4) . 2_645
Br2 Cu S11 94.37(4) . 2_645
N11 Cu S1 145.57(12) 2_645 .
N1 Cu S1 54.27(13) . .
Br1 Cu S1 72.28(3) . .
Br2 Cu S1 85.88(4) . .
S11 Cu S1 155.62(4) 2_645 .
S1 C1 S11 109.1(2) . .
C2 S1 C1 103.4(2) . .
C2 S1 Cu 65.43(16) . .
C1 S1 Cu 152.45(17) . .
C2 N1 C6 118.8(4) . .
C2 N1 Cu 124.6(3) . .
C6 N1 Cu 116.5(3) . .
N1 C2 C3 120.5(5) . .
N1 C2 S1 115.4(4) . .
C3 C2 S1 124.1(4) . .
C4 C3 C2 119.2(5) . .
C5 C4 C3 119.6(5) . .
C6 C5 C4 118.9(5) . .
N1 C6 C5 122.9(5) . .
C12 S11 C1 101.5(2) . .
C12 N11 C16 118.0(4) . .
C12 N11 Cu 117.8(3) . 2_655
C16 N11 Cu 124.2(4) . 2_655
N11 C12 C13 122.2(5) . .
N11 C12 S11 115.7(4) . .
C13 C12 S11 122.2(4) . .
C14 C13 C12 118.7(5) . .
C13 C14 C15 120.2(5) . .
C14 C15 C16 118.3(5) . .
N11 C16 C15 122.6(5) . .
N111 C111 C112 178.9(7) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cu N11 2.011(4) 2_645
Cu N1 2.011(4) .
Cu Br1 2.4031(9) .
Cu Br2 2.4064(9) .
Cu S11 3.0582(16) 2_645
Cu S1 3.2522(15) .
C1 S1 1.794(5) .
C1 S11 1.816(5) .
S1 C2 1.771(5) .
N1 C2 1.344(6) .
N1 C6 1.353(6) .
C2 C3 1.394(6) .
C3 C4 1.379(6) .
C4 C5 1.368(7) .
C5 C6 1.354(6) .
S11 C12 1.773(5) .
N11 C12 1.346(6) .
N11 C16 1.352(6) .
N11 Cu 2.011(4) 2_655
C12 C13 1.389(6) .
C13 C14 1.369(7) .
C14 C15 1.376(7) .
C15 C16 1.383(6) .
N111 C111 1.128(7) .
C111 C112 1.457(8) .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C1 H1A Br2 0.97 2.85 3.713(5) 148.5 2_655
C4 H4 N111 0.93 2.61 3.248(8) 126.6 1_655
C6 H6 S11 0.93 2.88 3.681(5) 145.2 2_645
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
S11 C1 S1 C2 -71.2(3) .
S11 C1 S1 Cu -9.0(6) .
N11 Cu S1 C2 -177.5(3) 2_645
N1 Cu S1 C2 -2.9(2) .
Br1 Cu S1 C2 -110.60(17) .
Br2 Cu S1 C2 91.00(17) .
S11 Cu S1 C2 -0.5(2) 2_645
N11 Cu S1 C1 111.4(4) 2_645
N1 Cu S1 C1 -73.9(4) .
Br1 Cu S1 C1 178.3(4) .
Br2 Cu S1 C1 19.9(4) .
S11 Cu S1 C1 -71.6(4) 2_645
N11 Cu N1 C2 175.4(4) 2_645
Br1 Cu N1 C2 69.5(4) .
Br2 Cu N1 C2 -80.3(4) .
S11 Cu N1 C2 -174.9(3) 2_645
S1 Cu N1 C2 4.2(3) .
N11 Cu N1 C6 -7.5(7) 2_645
Br1 Cu N1 C6 -113.4(3) .
Br2 Cu N1 C6 96.8(3) .
S11 Cu N1 C6 2.2(4) 2_645
S1 Cu N1 C6 -178.8(4) .
C6 N1 C2 C3 -1.6(7) .
Cu N1 C2 C3 175.5(3) .
C6 N1 C2 S1 176.1(3) .
Cu N1 C2 S1 -6.9(5) .
C1 S1 C2 N1 157.1(4) .
Cu S1 C2 N1 3.8(3) .
C1 S1 C2 C3 -25.3(5) .
Cu S1 C2 C3 -178.6(5) .
N1 C2 C3 C4 1.5(7) .
S1 C2 C3 C4 -175.9(4) .
C2 C3 C4 C5 -0.6(8) .
C3 C4 C5 C6 -0.2(8) .
C2 N1 C6 C5 0.7(7) .
Cu N1 C6 C5 -176.5(4) .
C4 C5 C6 N1 0.1(8) .
S1 C1 S11 C12 177.8(3) .
C16 N11 C12 C13 -2.9(7) .
Cu N11 C12 C13 178.2(4) 2_655
C16 N11 C12 S11 177.0(4) .
Cu N11 C12 S11 -1.9(5) 2_655
C1 S11 C12 N11 100.8(4) .
C1 S11 C12 C13 -79.3(5) .
N11 C12 C13 C14 3.1(8) .
S11 C12 C13 C14 -176.7(4) .
C12 C13 C14 C15 -1.6(8) .
C13 C14 C15 C16 -0.1(8) .
C12 N11 C16 C15 1.1(7) .
Cu N11 C16 C15 179.9(4) 2_655
C14 C15 C16 N11 0.4(8) .
