#------------------------------------------------------------------------------
#$Date: 2016-02-16 22:30:59 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176467 $
#$URL: svn://www.crystallography.net/cod/cif/4/32/07/4320753.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_4320753
loop_
_publ_author_name
'Ramaswamy Murugavel'
'Kanhayalal Baheti'
'Ganapathi Anantharaman'
_publ_section_title
;
 Reactions of 2-Mercaptobenzoic Acid with Divalent Alkaline Earth Metal
 Ions: Synthesis, Spectral Studies, and Single-Crystal X-ray Structures of
 Calcium, Strontium, and Barium Complexes of 2,2'-Dithiobis(benzoic acid),
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              6870
_journal_page_last               6878
_journal_paper_doi               10.1021/ic010519b
_journal_volume                  40
_journal_year                    2001
_chemical_formula_sum            'C15.5 H12 Ca N0 O6 S2'
_chemical_formula_weight         398.45
_chemical_name_systematic
;
?
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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                 114.34(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   22.549(11)
_cell_length_b                   7.538(2)
_cell_length_c                   21.597(5)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      13.76
_cell_measurement_theta_min      7.43
_cell_volume                     3345(2)
_computing_cell_refinement       'CAD4 Express (Enraf Nonius, 1994)'
_computing_data_collection       'CAD4 Express (Enraf Nonius, 1994)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'CIFTAB (sheldrick)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0070
_diffrn_reflns_av_sigmaI/netI    0.0231
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -2
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -2
_diffrn_reflns_number            3115
_diffrn_reflns_theta_full        24.95
_diffrn_reflns_theta_max         24.95
_diffrn_reflns_theta_min         1.98
_exptl_absorpt_coefficient_mu    0.654
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.583
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       blocks
_exptl_crystal_F_000             1640
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.392
_refine_diff_density_min         -0.319
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     222
_refine_ls_number_reflns         2927
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.079
_refine_ls_R_factor_all          0.0430
_refine_ls_R_factor_gt           0.0341
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0495P)²+3.8647P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0949
_refine_ls_wR_factor_ref         0.0987
_reflns_number_gt                2422
_reflns_number_total             2927
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic010519b_1.cif
_cod_data_source_block           Complex1(Ca_compound)
_cod_original_formula_sum        'C15.50 H12 Ca N0 O6 S2'
_cod_database_code               4320753
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Ca1 Ca -0.01185(2) 0.25277(6) 0.50976(2) 0.02673(15) Uani 1 1 d . . .
S1 S 0.08614(3) 0.24971(9) 0.33196(3) 0.03951(19) Uani 1 1 d . . .
S2 S 0.10269(3) 0.27075(9) 0.24606(3) 0.03920(19) Uani 1 1 d . . .
O1 O 0.03676(12) 0.4027(3) 0.62156(9) 0.0613(6) Uani 1 1 d . . .
H1B H 0.0378 0.3587 0.6608 0.080 Uiso 1 1 d R . .
H1A H 0.0522 0.5025 0.6172 0.080 Uiso 1 1 d R . .
O2 O -0.07785(10) 0.1288(3) 0.56052(11) 0.0560(6) Uani 1 1 d . . .
H2B H -0.1025 0.1912 0.5766 0.080 Uiso 1 1 d R . .
H2A H -0.0747 0.0164 0.5611 0.080 Uiso 1 1 d R . .
O3 O 0.06957(8) 0.4730(2) 0.50323(9) 0.0386(4) Uani 1 1 d . . .
O4 O 0.05760(10) 0.2281(2) 0.44509(10) 0.0420(5) Uani 1 1 d . . .
O5 O 0.06049(8) -0.0160(2) 0.06470(8) 0.0341(4) Uani 1 1 d . . .
O6 O 0.09188(9) 0.2469(2) 0.11116(9) 0.0394(4) Uani 1 1 d . . .
C1 C 0.08707(11) 0.3691(3) 0.46817(11) 0.0272(5) Uani 1 1 d . . .
C2 C 0.14648(11) 0.4125(3) 0.45653(11) 0.0274(5) Uani 1 1 d . . .
C3 C 0.15339(11) 0.3596(3) 0.39747(11) 0.0291(5) Uani 1 1 d . . .
C4 C 0.21066(12) 0.3963(4) 0.39131(13) 0.0376(6) Uani 1 1 d . . .
H4A H 0.2148 0.3654 0.3501 0.080 Uiso 1 1 d R . .
C5 C 0.26161(13) 0.4785(4) 0.44354(14) 0.0425(6) Uani 1 1 d . . .
H5A H 0.3021 0.4978 0.4397 0.080 Uiso 1 1 d R . .
C6 C 0.25495(13) 0.5310(4) 0.50143(14) 0.0434(6) Uani 1 1 d . . .
H6A H 0.2901 0.5898 0.5375 0.080 Uiso 1 1 d R . .
C7 C 0.19707(13) 0.5004(3) 0.50693(12) 0.0379(6) Uani 1 1 d . . .
H7A H 0.1918 0.5406 0.5465 0.080 Uiso 1 1 d R . .
C11 C 0.09243(11) 0.0817(3) 0.11506(11) 0.0276(5) Uani 1 1 d . . .
C12 C 0.13389(11) -0.0053(3) 0.18122(11) 0.0284(5) Uani 1 1 d . . .
C13 C 0.14295(11) 0.0683(3) 0.24403(11) 0.0306(5) Uani 1 1 d . . .
C14 C 0.18260(13) -0.0189(4) 0.30374(12) 0.0422(6) Uani 1 1 d . . .
H14A H 0.1886 0.0310 0.3468 0.080 Uiso 1 1 d R . .
C15 C 0.21289(15) -0.1749(4) 0.30122(15) 0.0512(7) Uani 1 1 d . . .
H15A H 0.2408 -0.2319 0.3428 0.080 Uiso 1 1 d R . .
C16 C 0.20381(14) -0.2505(4) 0.24020(15) 0.0480(7) Uani 1 1 d . . .
H16A H 0.2244 -0.3611 0.2391 0.080 Uiso 1 1 d R . .
C17 C 0.16439(12) -0.1662(4) 0.18040(13) 0.0388(6) Uani 1 1 d . . .
H17A H 0.1580 -0.2184 0.1376 0.080 Uiso 1 1 d R . .
C98 C 0.0000 0.1828(16) 0.7500 0.192(5) Uani 1 2 d S . .
C99 C -0.0541(3) 0.2877(8) 0.6939(4) 0.134(2) 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'
O O 0.0106 0.0060 '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'
Ca Ca 0.2262 0.3064 '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
_geom_angle_publ_flag
O2 Ca1 O5 84.59(7) . 6_556 ?
O2 Ca1 O3 88.87(7) . 5_566 ?
O5 Ca1 O3 158.93(6) 6_556 5_566 ?
O2 Ca1 O1 80.75(8) . . ?
O5 Ca1 O1 85.36(7) 6_556 . ?
O3 Ca1 O1 73.81(7) 5_566 . ?
O2 Ca1 O6 98.99(8) . 2 ?
O5 Ca1 O6 124.17(6) 6_556 2 ?
O3 Ca1 O6 76.62(6) 5_566 2 ?
O1 Ca1 O6 150.43(7) . 2 ?
O2 Ca1 O4 152.33(7) . . ?
O5 Ca1 O4 76.34(7) 6_556 . ?
O3 Ca1 O4 115.73(6) 5_566 . ?
O1 Ca1 O4 116.86(8) . . ?
O6 Ca1 O4 76.26(7) 2 . ?
O2 Ca1 O3 153.44(7) . . ?
O5 Ca1 O3 98.99(7) 6_556 . ?
O3 Ca1 O3 78.37(7) 5_566 . ?
O1 Ca1 O3 73.38(7) . . ?
O6 Ca1 O3 100.53(7) 2 . ?
O4 Ca1 O3 51.63(6) . . ?
O2 Ca1 O5 77.81(7) . 2 ?
O5 Ca1 O5 75.26(7) 6_556 2 ?
O3 Ca1 O5 122.85(7) 5_566 2 ?
O1 Ca1 O5 152.21(6) . 2 ?
O6 Ca1 O5 51.96(5) 2 2 ?
O4 Ca1 O5 78.05(6) . 2 ?
O3 Ca1 O5 128.65(6) . 2 ?
O2 Ca1 C11 88.97(7) . 2 ?
O5 Ca1 C11 99.80(7) 6_556 2 ?
O3 Ca1 C11 100.09(7) 5_566 2 ?
O1 Ca1 C11 168.05(8) . 2 ?
O6 Ca1 C11 25.78(6) 2 2 ?
O4 Ca1 C11 74.98(7) . 2 ?
O3 Ca1 C11 115.98(6) . 2 ?
O5 Ca1 C11 26.20(6) 2 2 ?
O2 Ca1 C1 169.40(7) . . ?
O5 Ca1 C1 85.62(7) 6_556 . ?
O3 Ca1 C1 98.89(7) 5_566 . ?
O1 Ca1 C1 94.42(8) . . ?
O6 Ca1 C1 89.88(7) 2 . ?
O4 Ca1 C1 25.69(6) . . ?
O3 Ca1 C1 26.08(6) . . ?
O5 Ca1 C1 103.59(6) 2 . ?
C11 Ca1 C1 96.71(7) 2 . ?
O2 Ca1 Ca1 125.38(5) . 5_566 ?
O5 Ca1 Ca1 133.62(5) 6_556 5_566 ?
O3 Ca1 Ca1 40.37(5) 5_566 5_566 ?
O1 Ca1 Ca1 68.63(5) . 5_566 ?
O6 Ca1 Ca1 88.59(4) 2 5_566 ?
O4 Ca1 Ca1 82.09(4) . 5_566 ?
O3 Ca1 Ca1 38.00(4) . 5_566 ?
O5 Ca1 Ca1 138.93(4) 2 5_566 ?
C11 Ca1 Ca1 113.57(5) 2 5_566 ?
C1 Ca1 Ca1 60.21(5) . 5_566 ?
O2 Ca1 Ca1 78.75(5) . 5_556 ?
O5 Ca1 Ca1 39.05(4) 6_556 5_556 ?
O3 Ca1 Ca1 157.41(5) 5_566 5_556 ?
O1 Ca1 Ca1 121.80(5) . 5_556 ?
O6 Ca1 Ca1 86.65(4) 2 5_556 ?
O4 Ca1 Ca1 73.79(4) . 5_556 ?
O3 Ca1 Ca1 120.16(5) . 5_556 ?
O5 Ca1 Ca1 36.20(4) 2 5_556 ?
C11 Ca1 Ca1 61.28(5) 2 5_556 ?
C1 Ca1 Ca1 96.11(5) . 5_556 ?
Ca1 Ca1 Ca1 155.86(3) 5_566 5_556 ?
C3 S1 S2 105.59(9) . . ?
C13 S2 S1 103.94(8) . . ?
C1 O3 Ca1 139.00(15) . 5_566 ?
C1 O3 Ca1 92.32(14) . . ?
Ca1 O3 Ca1 101.63(7) 5_566 . ?
C1 O4 Ca1 93.82(14) . . ?
C11 O5 Ca1 153.70(15) . 6 ?
C11 O5 Ca1 91.40(14) . 2 ?
Ca1 O5 Ca1 104.74(7) 6 2 ?
C11 O6 Ca1 94.08(14) . 2 ?
O4 C1 O3 121.6(2) . . ?
O4 C1 C2 119.1(2) . . ?
O3 C1 C2 119.3(2) . . ?
O4 C1 Ca1 60.49(12) . . ?
O3 C1 Ca1 61.61(12) . . ?
C2 C1 Ca1 170.31(15) . . ?
C7 C2 C3 119.2(2) . . ?
C7 C2 C1 118.6(2) . . ?
C3 C2 C1 122.2(2) . . ?
C4 C3 C2 119.3(2) . . ?
C4 C3 S1 122.49(18) . . ?
C2 C3 S1 118.23(18) . . ?
C3 C4 C5 120.5(2) . . ?
C6 C5 C4 120.3(2) . . ?
C5 C6 C7 119.5(2) . . ?
C6 C7 C2 121.1(2) . . ?
O6 C11 O5 122.5(2) . . ?
O6 C11 C12 119.1(2) . . ?
O5 C11 C12 118.4(2) . . ?
O6 C11 Ca1 60.14(12) . 2 ?
O5 C11 Ca1 62.40(12) . 2 ?
C12 C11 Ca1 178.67(16) . 2 ?
C17 C12 C13 118.7(2) . . ?
C17 C12 C11 119.0(2) . . ?
C13 C12 C11 122.3(2) . . ?
C14 C13 C12 119.4(2) . . ?
C14 C13 S2 121.26(19) . . ?
C12 C13 S2 119.34(17) . . ?
C15 C14 C13 120.5(2) . . ?
C16 C15 C14 120.9(3) . . ?
C15 C16 C17 119.4(3) . . ?
C16 C17 C12 121.1(2) . . ?
C99 C98 C99 118.1(10) . 2_556 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ca1 O2 2.374(2) . ?
Ca1 O5 2.3790(18) 6_556 ?
Ca1 O3 2.3971(19) 5_566 ?
Ca1 O1 2.475(2) . ?
Ca1 O6 2.489(2) 2 ?
Ca1 O4 2.498(2) . ?
Ca1 O3 2.522(2) . ?
Ca1 O5 2.5376(18) 2 ?
Ca1 C11 2.863(2) 2 ?
Ca1 C1 2.864(3) . ?
Ca1 Ca1 3.8133(15) 5_566 ?
Ca1 Ca1 3.8951(15) 5_556 ?
S1 C3 1.794(2) . ?
S1 S2 2.0439(10) . ?
S2 C13 1.785(3) . ?
O3 C1 1.260(3) . ?
O3 Ca1 2.3971(19) 5_566 ?
O4 C1 1.244(3) . ?
O5 C11 1.264(3) . ?
O5 Ca1 2.3790(18) 6 ?
O5 Ca1 2.5376(18) 2 ?
O6 C11 1.248(3) . ?
O6 Ca1 2.489(2) 2 ?
C1 C2 1.497(3) . ?
C2 C7 1.379(3) . ?
C2 C3 1.405(3) . ?
C3 C4 1.380(3) . ?
C4 C5 1.382(4) . ?
C5 C6 1.377(4) . ?
C6 C7 1.378(4) . ?
C11 C12 1.498(3) . ?
C11 Ca1 2.863(2) 2 ?
C12 C17 1.398(3) . ?
C12 C13 1.401(3) . ?
C13 C14 1.394(3) . ?
C14 C15 1.373(4) . ?
C15 C16 1.372(4) . ?
C16 C17 1.384(4) . ?
C98 C99 1.537(8) . ?
C98 C99 1.537(8) 2_556 ?
