#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/22/2232216.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2232216
loop_
_publ_author_name
'Mandal, Soumik'
'Nethi, Vamsidhar'
'Gupta, Parna'
_publ_section_title
;
 Bis{μ-(E)-methyl
 4-[(2-carbamothioylhydrazinylidene)methyl]benzoate-κ²S:S}bis[iodido(triphenylphosphane-κP)copper(I)]
;
_journal_coeditor_code           DS2140
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m1535
_journal_paper_doi               10.1107/S1600536811041845
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          '[Cu2 I2 (C10 H11 N3 O2 S)2 (C18 H15 P)2]'
_chemical_formula_moiety         'C56 H52 Cu2 I2 N6 O4 P2 S2'
_chemical_formula_sum            'C56 H52 Cu2 I2 N6 O4 P2 S2'
_chemical_formula_weight         1380.02
_chemical_name_systematic
;
Bis{μ-(E)-methyl 4-[(2-carbamothioylhydrazinylidene)methyl]benzoate-
κ²S:S}bis[iodido(triphenylphosphane-κP)copper(I)]
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                108.627(4)
_cell_angle_beta                 101.655(4)
_cell_angle_gamma                105.044(3)
_cell_formula_units_Z            1
_cell_length_a                   9.6319(16)
_cell_length_b                   11.945(2)
_cell_length_c                   13.581(4)
_cell_measurement_reflns_used    4585
_cell_measurement_temperature    100
_cell_measurement_theta_max      28.24
_cell_measurement_theta_min      2.30
_cell_volume                     1358.9(5)
_computing_cell_refinement       'SAINT (Bruker, 2008)'
_computing_data_collection       'APEX2 (Bruker, 2008)'
_computing_data_reduction        'SAINT (Bruker, 2008)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'φ and ω'
_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  0.0652
_diffrn_reflns_av_sigmaI/netI    0.0675
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            22347
_diffrn_reflns_theta_full        26.99
_diffrn_reflns_theta_max         26.99
_diffrn_reflns_theta_min         1.67
_exptl_absorpt_coefficient_mu    2.107
_exptl_absorpt_correction_T_max  0.827
_exptl_absorpt_correction_T_min  0.757
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2008)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.684
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.09
_refine_diff_density_max         1.559
_refine_diff_density_min         -0.818
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     335
_refine_ls_number_reflns         5922
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.016
_refine_ls_R_factor_all          0.0601
_refine_ls_R_factor_gt           0.0360
_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)+(0.0265P)²+0.8634P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0664
_refine_ls_wR_factor_ref         0.0730
_reflns_number_gt                4560
_reflns_number_total             5922
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ds2140.cif
_cod_data_source_block           I
_cod_original_cell_volume        1359.0(5)
_cod_database_code               2232216
_cod_database_fobs_code          2232216
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
Cu Cu1 0.44847(4) 0.99151(4) 0.39202(4) 0.01460(11) Uani d . 1 1
I I1 0.44275(2) 1.19639(2) 0.35819(2) 0.01695(7) Uani d . 1 1
S S1 0.70887(9) 1.06875(7) 0.50340(8) 0.01341(19) Uani d . 1 1
P P1 0.36351(9) 0.82308(7) 0.23174(8) 0.01134(19) Uani d . 1 1
O O1 0.9554(3) 0.1581(2) 0.2812(2) 0.0209(6) Uani d . 1 1
O O2 1.0438(3) 0.2624(2) 0.1819(2) 0.0216(6) Uani d . 1 1
N N1 0.7579(3) 0.8525(2) 0.4633(3) 0.0153(7) Uani d . 1 1
H H1 0.7016 0.8385 0.5030 0.018 Uiso calc R 1 1
N N2 0.8214(3) 0.7653(3) 0.4179(3) 0.0178(7) Uani d . 1 1
N N3 0.8721(3) 0.9774(3) 0.3848(3) 0.0190(7) Uani d . 1 1
H H3A 0.9110 0.9222 0.3577 0.023 Uiso calc R 1 1
H H3B 0.8903 1.0452 0.3724 0.023 Uiso calc R 1 1
C C1 0.4266(3) 0.8438(3) 0.1181(3) 0.0124(7) Uani d . 1 1
C C2 0.3426(4) 0.7719(3) 0.0089(3) 0.0158(8) Uani d . 1 1
H H2 0.2443 0.7175 -0.0092 0.019 Uiso calc R 1 1
C C3 0.4045(4) 0.7809(3) -0.0733(3) 0.0187(8) Uani d . 1 1
H H3 0.3484 0.7315 -0.1462 0.022 Uiso calc R 1 1
C C4 0.5499(4) 0.8635(3) -0.0468(3) 0.0177(8) Uani d . 1 1
H H4 0.5918 0.8688 -0.1018 0.021 Uiso calc R 1 1
C C5 0.6322(4) 0.9377(3) 0.0606(3) 0.0179(8) Uani d . 1 1
H H5 0.7291 0.9942 0.0776 0.021 Uiso calc R 1 1
C C6 0.5724(3) 0.9295(3) 0.1446(3) 0.0148(8) Uani d . 1 1
H H6 0.6287 0.9804 0.2171 0.018 Uiso calc R 1 1
C C7 0.1577(4) 0.7719(3) 0.1779(3) 0.0140(7) Uani d . 1 1
C C8 0.0617(4) 0.6465(3) 0.1235(3) 0.0193(8) Uani d . 1 1
H H8 0.1016 0.5821 0.1127 0.023 Uiso calc R 1 1
C C9 -0.0938(4) 0.6175(3) 0.0851(3) 0.0244(9) Uani d . 1 1
H H9 -0.1572 0.5336 0.0494 0.029 Uiso calc R 1 1
C C10 -0.1549(4) 0.7110(3) 0.0992(4) 0.0242(9) Uani d . 1 1
H H10 -0.2590 0.6905 0.0733 0.029 Uiso calc R 1 1
C C11 -0.0610(4) 0.8364(3) 0.1523(3) 0.0223(9) Uani d . 1 1
H H11 -0.1018 0.9001 0.1607 0.027 Uiso calc R 1 1
C C12 0.0937(4) 0.8664(3) 0.1926(3) 0.0186(8) Uani d . 1 1
H H12 0.1560 0.9505 0.2300 0.022 Uiso calc R 1 1
C C13 0.3993(3) 0.6799(3) 0.2321(3) 0.0120(7) Uani d . 1 1
C C14 0.4589(4) 0.6129(3) 0.1569(3) 0.0195(8) Uani d . 1 1
H H14 0.4803 0.6399 0.1028 0.023 Uiso calc R 1 1
C C15 0.4858(4) 0.5062(3) 0.1631(3) 0.0208(9) Uani d . 1 1
H H15 0.5253 0.4623 0.1129 0.025 Uiso calc R 1 1
C C16 0.4549(4) 0.4645(3) 0.2425(3) 0.0196(8) Uani d . 1 1
H H16 0.4725 0.3925 0.2454 0.023 Uiso calc R 1 1
C C17 0.3975(4) 0.5306(3) 0.3180(3) 0.0231(9) Uani d . 1 1
H H17 0.3759 0.5026 0.3716 0.028 Uiso calc R 1 1
C C18 0.3722(4) 0.6386(3) 0.3138(3) 0.0178(8) Uani d . 1 1
H H18 0.3367 0.6839 0.3662 0.021 Uiso calc R 1 1
C C19 0.7841(3) 0.9580(3) 0.4455(3) 0.0145(8) Uani d . 1 1
C C20 0.7924(4) 0.6687(3) 0.4428(3) 0.0176(8) Uani d . 1 1
H H20 0.7346 0.6633 0.4894 0.021 Uiso calc R 1 1
C C21 0.8490(4) 0.5666(3) 0.3989(3) 0.0166(8) Uani d . 1 1
C C22 0.8040(4) 0.4589(3) 0.4212(3) 0.0173(8) Uani d . 1 1
H H22 0.7422 0.4548 0.4654 0.021 Uiso calc R 1 1
C C23 0.8497(4) 0.3586(3) 0.3787(3) 0.0160(8) Uani d . 1 1
H H23 0.8207 0.2882 0.3955 0.019 Uiso calc R 1 1
C C24 0.9396(4) 0.3629(3) 0.3104(3) 0.0142(8) Uani d . 1 1
C C25 0.9797(4) 0.2505(3) 0.2592(3) 0.0157(8) Uani d . 1 1
C C26 1.0860(4) 0.1589(3) 0.1253(4) 0.0257(9) Uani d . 1 1
H H26A 1.1516 0.1418 0.1774 0.038 Uiso calc R 1 1
H H26B 1.1378 0.1804 0.0768 0.038 Uiso calc R 1 1
H H26C 0.9969 0.0855 0.0838 0.038 Uiso calc R 1 1
C C27 0.9853(4) 0.4709(3) 0.2880(3) 0.0197(8) Uani d . 1 1
H H27 1.0460 0.4748 0.2430 0.024 Uiso calc R 1 1
C C28 0.9406(4) 0.5719(3) 0.3325(3) 0.0206(8) Uani d . 1 1
H H28 0.9721 0.6437 0.3179 0.025 Uiso calc R 1 1
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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 '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'
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
P1 Cu1 S1 . 2_676 104.59(4)
P1 Cu1 S1 . . 120.16(3)
S1 Cu1 S1 2_676 . 108.22(3)
P1 Cu1 I1 . . 110.45(3)
S1 Cu1 I1 2_676 . 115.32(3)
S1 Cu1 I1 . . 98.61(2)
P1 Cu1 Cu1 . 2_676 130.06(4)
S1 Cu1 Cu1 2_676 2_676 54.16(3)
S1 Cu1 Cu1 . 2_676 54.05(3)
I1 Cu1 Cu1 . 2_676 119.49(2)
C19 S1 Cu1 . 2_676 113.92(13)
C19 S1 Cu1 . . 106.03(11)
Cu1 S1 Cu1 2_676 . 71.78(3)
C7 P1 C1 . . 103.42(17)
C7 P1 C13 . . 104.04(14)
C1 P1 C13 . . 102.23(15)
C7 P1 Cu1 . . 109.73(12)
C1 P1 Cu1 . . 117.80(11)
C13 P1 Cu1 . . 117.87(12)
C25 O2 C26 . . 116.7(3)
C19 N1 N2 . . 119.7(3)
C19 N1 H1 . . 120.1
N2 N1 H1 . . 120.1
C20 N2 N1 . . 114.6(3)
C19 N3 H3A . . 120.0
C19 N3 H3B . . 120.0
H3A N3 H3B . . 120.0
C2 C1 C6 . . 119.4(3)
C2 C1 P1 . . 123.3(2)
C6 C1 P1 . . 117.1(3)
C3 C2 C1 . . 120.5(3)
C3 C2 H2 . . 119.8
C1 C2 H2 . . 119.8
C4 C3 C2 . . 119.9(4)
C4 C3 H3 . . 120.0
C2 C3 H3 . . 120.0
C5 C4 C3 . . 120.1(4)
C5 C4 H4 . . 119.9
C3 C4 H4 . . 119.9
C4 C5 C6 . . 120.8(3)
C4 C5 H5 . . 119.6
C6 C5 H5 . . 119.6
C5 C6 C1 . . 119.2(3)
C5 C6 H6 . . 120.4
C1 C6 H6 . . 120.4
C8 C7 C12 . . 118.4(3)
C8 C7 P1 . . 124.6(3)
C12 C7 P1 . . 117.0(2)
C9 C8 C7 . . 120.1(3)
C9 C8 H8 . . 120.0
C7 C8 H8 . . 120.0
C10 C9 C8 . . 120.9(3)
C10 C9 H9 . . 119.6
C8 C9 H9 . . 119.6
C9 C10 C11 . . 119.9(3)
C9 C10 H10 . . 120.1
C11 C10 H10 . . 120.1
C12 C11 C10 . . 119.8(3)
C12 C11 H11 . . 120.1
C10 C11 H11 . . 120.1
C11 C12 C7 . . 120.9(3)
C11 C12 H12 . . 119.5
C7 C12 H12 . . 119.5
C18 C13 C14 . . 118.4(3)
C18 C13 P1 . . 118.5(3)
C14 C13 P1 . . 123.0(3)
C15 C14 C13 . . 120.1(4)
C15 C14 H14 . . 120.0
C13 C14 H14 . . 120.0
C16 C15 C14 . . 121.0(4)
C16 C15 H15 . . 119.5
C14 C15 H15 . . 119.5
C15 C16 C17 . . 119.5(3)
C15 C16 H16 . . 120.2
C17 C16 H16 . . 120.2
C16 C17 C18 . . 120.1(4)
C16 C17 H17 . . 120.0
C18 C17 H17 . . 120.0
C17 C18 C13 . . 120.9(3)
C17 C18 H18 . . 119.5
C13 C18 H18 . . 119.5
N3 C19 N1 . . 118.8(3)
N3 C19 S1 . . 120.9(3)
N1 C19 S1 . . 120.3(3)
N2 C20 C21 . . 121.1(3)
N2 C20 H20 . . 119.5
C21 C20 H20 . . 119.5
C28 C21 C22 . . 119.2(3)
C28 C21 C20 . . 122.0(3)
C22 C21 C20 . . 118.8(3)
C23 C22 C21 . . 121.0(3)
C23 C22 H22 . . 119.5
C21 C22 H22 . . 119.5
C22 C23 C24 . . 119.9(3)
C22 C23 H23 . . 120.1
C24 C23 H23 . . 120.1
C23 C24 C27 . . 119.3(3)
C23 C24 C25 . . 119.3(3)
C27 C24 C25 . . 121.4(3)
O1 C25 O2 . . 123.5(3)
O1 C25 C24 . . 125.2(3)
O2 C25 C24 . . 111.3(3)
O2 C26 H26A . . 109.5
O2 C26 H26B . . 109.5
H26A C26 H26B . . 109.5
O2 C26 H26C . . 109.5
H26A C26 H26C . . 109.5
H26B C26 H26C . . 109.5
C28 C27 C24 . . 120.3(4)
C28 C27 H27 . . 119.8
C24 C27 H27 . . 119.8
C27 C28 C21 . . 120.3(3)
C27 C28 H28 . . 119.9
C21 C28 H28 . . 119.9
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
Cu1 P1 . 2.2548(10)
Cu1 S1 2_676 2.4060(10)
Cu1 S1 . 2.4093(10)
Cu1 I1 . 2.6423(6)
Cu1 Cu1 2_676 2.8228(12)
S1 C19 . 1.720(3)
S1 Cu1 2_676 2.4059(10)
P1 C7 . 1.827(3)
P1 C1 . 1.832(4)
P1 C13 . 1.832(3)
O1 C25 . 1.212(4)
O2 C25 . 1.347(4)
O2 C26 . 1.437(4)
N1 C19 . 1.329(4)
N1 N2 . 1.383(4)
N1 H1 . 0.8600
N2 C20 . 1.282(5)
N3 C19 . 1.325(5)
N3 H3A . 0.8600
N3 H3B . 0.8600
C1 C2 . 1.390(5)
C1 C6 . 1.402(4)
C2 C3 . 1.388(5)
C2 H2 . 0.9300
C3 C4 . 1.384(5)
C3 H3 . 0.9300
C4 C5 . 1.372(5)
C4 H4 . 0.9300
C5 C6 . 1.396(5)
C5 H5 . 0.9300
C6 H6 . 0.9300
C7 C8 . 1.394(4)
C7 C12 . 1.401(5)
C8 C9 . 1.391(5)
C8 H8 . 0.9300
C9 C10 . 1.371(5)
C9 H9 . 0.9300
C10 C11 . 1.387(5)
C10 H10 . 0.9300
C11 C12 . 1.384(5)
C11 H11 . 0.9300
C12 H12 . 0.9300
C13 C18 . 1.394(5)
C13 C14 . 1.402(5)
C14 C15 . 1.389(5)
C14 H14 . 0.9300
C15 C16 . 1.377(6)
C15 H15 . 0.9300
C16 C17 . 1.385(5)
C16 H16 . 0.9300
C17 C18 . 1.390(5)
C17 H17 . 0.9300
C18 H18 . 0.9300
C20 C21 . 1.467(5)
C20 H20 . 0.9300
C21 C28 . 1.387(5)
C21 C22 . 1.395(5)
C22 C23 . 1.377(5)
C22 H22 . 0.9300
C23 C24 . 1.394(5)
C23 H23 . 0.9300
C24 C27 . 1.400(5)
C24 C25 . 1.489(5)
C26 H26A . 0.9600
C26 H26B . 0.9600
C26 H26C . 0.9600
C27 C28 . 1.384(5)
C27 H27 . 0.9300
C28 H28 . 0.9300
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N3 H3B O1 1_565 0.860 2.165 2.963(5) 154.09 yes
