#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/32/07/4320756.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_4320756
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            'C28 H23 N O8 S4'
_chemical_formula_weight         629.71
_chemical_name_systematic
;
?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 94.006(11)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.3619(9)
_cell_length_b                   12.0443(10)
_cell_length_c                   21.126(3)
_cell_measurement_temperature    203(2)
_cell_volume                     2883.9(5)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      203(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_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  0.0325
_diffrn_reflns_av_sigmaI/netI    0.0397
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            5841
_diffrn_reflns_theta_full        22.53
_diffrn_reflns_theta_max         22.53
_diffrn_reflns_theta_min         3.52
_exptl_absorpt_coefficient_mu    0.381
_exptl_absorpt_correction_T_max  0.8944
_exptl_absorpt_correction_T_min  0.8627
_exptl_crystal_density_diffrn    1.450
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1304
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.268
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     462
_refine_ls_number_reflns         3773
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0612
_refine_ls_R_factor_gt           0.0421
_refine_ls_shift/su_max          0.013
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0306P)²+2.5310P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0859
_refine_ls_wR_factor_ref         0.0969
_reflns_number_gt                2917
_reflns_number_total             3773
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic010519b_4.cif
_cod_data_source_block           Complex4(NH4_Adduct)
_cod_database_code               4320756
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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
S1 S 0.39374(9) 0.34819(7) 0.13627(5) 0.0535(3) Uani 1 1 d . . .
O11 O 0.5011(3) 0.6834(2) 0.08702(14) 0.0594(8) Uani 1 1 d . . .
O12 O 0.3741(3) 0.5630(2) 0.12154(16) 0.0733(10) Uani 1 1 d . . .
C1 C 0.4686(4) 0.5824(3) 0.10119(17) 0.0441(10) Uani 1 1 d . . .
C11 C 0.5551(3) 0.4947(3) 0.08954(16) 0.0381(9) Uani 1 1 d . . .
C12 C 0.6617(4) 0.5214(3) 0.0648(2) 0.0536(11) Uani 1 1 d . . .
C13 C 0.7437(4) 0.4417(4) 0.0551(2) 0.0670(14) Uani 1 1 d . . .
C14 C 0.7219(4) 0.3333(4) 0.0704(2) 0.0617(12) Uani 1 1 d . . .
C15 C 0.6171(4) 0.3042(3) 0.0951(2) 0.0507(11) Uani 1 1 d . . .
C16 C 0.5321(3) 0.3837(3) 0.10535(16) 0.0394(9) Uani 1 1 d . . .
S2 S 0.40558(9) 0.18331(7) 0.15788(4) 0.0455(3) Uani 1 1 d . . .
O21 O 0.3561(2) -0.17716(18) 0.14018(11) 0.0467(7) Uani 1 1 d . . .
O22 O 0.3457(2) -0.02413(18) 0.19783(12) 0.0417(6) Uani 1 1 d . . .
C2 C 0.3498(3) -0.0744(3) 0.14428(17) 0.0355(8) Uani 1 1 d . . .
C21 C 0.3447(3) -0.0047(3) 0.08605(16) 0.0357(8) Uani 1 1 d . . .
C22 C 0.3184(4) -0.0585(4) 0.02883(19) 0.0515(11) Uani 1 1 d . . .
C23 C 0.3117(4) -0.0028(4) -0.0279(2) 0.0663(13) Uani 1 1 d . . .
C24 C 0.3325(4) 0.1102(4) -0.0282(2) 0.0628(13) Uani 1 1 d . . .
C25 C 0.3590(4) 0.1659(3) 0.02767(19) 0.0499(10) Uani 1 1 d . . .
C26 C 0.3649(3) 0.1107(3) 0.08560(16) 0.0352(9) Uani 1 1 d . . .
S3 S 0.47447(8) 0.46836(7) 0.32493(5) 0.0433(3) Uani 1 1 d . . .
O31 O 0.6102(3) 0.1288(2) 0.32760(14) 0.0577(8) Uani 1 1 d . . .
O32 O 0.4684(2) 0.25308(19) 0.33715(12) 0.0468(7) Uani 1 1 d . . .
C3 C 0.5699(3) 0.2314(3) 0.32645(15) 0.0358(8) Uani 1 1 d . . .
C31 C 0.6561(3) 0.3174(3) 0.31387(15) 0.0342(8) Uani 1 1 d . . .
C32 C 0.6245(3) 0.4307(3) 0.31411(15) 0.0358(9) Uani 1 1 d . . .
C33 C 0.7112(4) 0.5086(4) 0.30386(18) 0.0491(10) Uani 1 1 d . . .
C34 C 0.8243(4) 0.4757(4) 0.2931(2) 0.0596(13) Uani 1 1 d . . .
C35 C 0.8546(4) 0.3662(4) 0.2911(2) 0.0616(12) Uani 1 1 d . . .
C36 C 0.7714(4) 0.2864(4) 0.30209(18) 0.0484(10) Uani 1 1 d . . .
S4 S 0.46703(10) 0.63578(7) 0.31002(4) 0.0495(3) Uani 1 1 d . . .
O41 O 0.4359(2) 0.98887(19) 0.34320(13) 0.0518(7) Uani 1 1 d . . .
O42 O 0.3724(2) 0.84353(18) 0.28636(11) 0.0398(6) Uani 1 1 d . . .
C4 C 0.4178(3) 0.8880(3) 0.33726(17) 0.0355(9) Uani 1 1 d . . .
C41 C 0.4479(3) 0.8120(3) 0.39229(16) 0.0340(8) Uani 1 1 d . . .
C42 C 0.4726(3) 0.6988(3) 0.38703(16) 0.0360(8) Uani 1 1 d . . .
C43 C 0.5037(4) 0.6383(3) 0.44153(18) 0.0466(10) Uani 1 1 d . . .
C44 C 0.5086(4) 0.6879(4) 0.5004(2) 0.0550(11) Uani 1 1 d . . .
C45 C 0.4825(4) 0.7996(4) 0.5060(2) 0.0562(12) Uani 1 1 d . . .
C46 C 0.4524(3) 0.8598(3) 0.45236(18) 0.0464(10) Uani 1 1 d . . .
N1 N 0.2371(4) 0.6548(4) 0.2103(2) 0.0222(7) Uani 1 1 d . . .
H12 H 0.673(4) 0.595(4) 0.056(2) 0.078(14) Uiso 1 1 d . . .
H13 H 0.817(4) 0.461(3) 0.0385(18) 0.066(13) Uiso 1 1 d . . .
H14 H 0.779(3) 0.279(3) 0.0636(17) 0.059(12) Uiso 1 1 d . . .
H15 H 0.603(3) 0.232(3) 0.1050(17) 0.054(12) Uiso 1 1 d . . .
H22 H 0.306(3) -0.134(3) 0.0317(17) 0.056(12) Uiso 1 1 d . . .
H23 H 0.289(3) -0.042(3) -0.066(2) 0.066(13) Uiso 1 1 d . . .
H24 H 0.329(4) 0.146(4) -0.066(2) 0.085(16) Uiso 1 1 d . . .
H25 H 0.372(3) 0.243(3) 0.0290(15) 0.040(10) Uiso 1 1 d . . .
H33 H 0.688(3) 0.585(3) 0.3050(18) 0.062(13) Uiso 1 1 d . . .
H34 H 0.877(4) 0.531(4) 0.2862(19) 0.072(14) Uiso 1 1 d . . .
H35 H 0.933(4) 0.343(3) 0.2849(19) 0.071(13) Uiso 1 1 d . . .
H36 H 0.793(3) 0.208(3) 0.3014(18) 0.064(12) Uiso 1 1 d . . .
H44 H 0.529(3) 0.649(3) 0.5356(19) 0.063(13) Uiso 1 1 d . . .
H43 H 0.528(3) 0.568(3) 0.4372(16) 0.042(10) Uiso 1 1 d . . .
H45 H 0.484(3) 0.829(4) 0.546(2) 0.074(14) Uiso 1 1 d . . .
H46 H 0.437(3) 0.939(3) 0.4553(16) 0.047(10) Uiso 1 1 d . . .
H5A H 0.271(4) 0.633(3) 0.1898(19) 0.039(17) Uiso 1 1 d . . .
H5B H 0.266(4) 0.690(4) 0.226(2) 0.04(2) Uiso 1 1 d . . .
H5C H 0.230(4) 0.618(4) 0.234(2) 0.056(19) Uiso 1 1 d . . .
H51 H 0.453(4) 0.735(4) 0.102(2) 0.094(17) Uiso 1 1 d . . .
H52 H 0.357(5) -0.089(5) 0.245(3) 0.129(19) Uiso 1 1 d . . .
H53 H 0.552(5) 0.082(5) 0.333(3) 0.12(2) Uiso 1 1 d . . .
H54 H 0.177(5) 0.681(4) 0.194(2) 0.084(19) Uiso 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'
S S 0.1246 0.1234 '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
_geom_angle_publ_flag
C16 S1 S2 105.52(12) . . ?
O12 C1 O11 122.2(3) . . ?
O12 C1 C11 122.7(3) . . ?
O11 C1 C11 115.1(3) . . ?
C12 C11 C16 119.4(3) . . ?
C12 C11 C1 120.3(3) . . ?
C16 C11 C1 120.3(3) . . ?
C13 C12 C11 121.1(4) . . ?
C12 C13 C14 119.9(4) . . ?
C13 C14 C15 120.4(4) . . ?
C14 C15 C16 120.9(4) . . ?
C15 C16 C11 118.4(3) . . ?
C15 C16 S1 122.0(3) . . ?
C11 C16 S1 119.7(3) . . ?
C26 S2 S1 105.98(12) . . ?
O21 C2 O22 122.4(3) . . ?
O21 C2 C21 120.2(3) . . ?
O22 C2 C21 117.4(3) . . ?
C22 C21 C26 118.7(3) . . ?
C22 C21 C2 116.9(3) . . ?
C26 C21 C2 124.4(3) . . ?
C23 C22 C21 122.0(4) . . ?
C22 C23 C24 119.1(4) . . ?
C25 C24 C23 120.3(4) . . ?
C24 C25 C26 121.2(4) . . ?
C25 C26 C21 118.7(3) . . ?
C25 C26 S2 120.7(3) . . ?
C21 C26 S2 120.5(3) . . ?
C32 S3 S4 105.05(12) . . ?
O32 C3 O31 122.0(3) . . ?
O32 C3 C31 122.4(3) . . ?
O31 C3 C31 115.6(3) . . ?
C36 C31 C32 120.0(3) . . ?
C36 C31 C3 119.3(3) . . ?
C32 C31 C3 120.7(3) . . ?
C33 C32 C31 118.0(3) . . ?
C33 C32 S3 122.7(3) . . ?
C31 C32 S3 119.3(3) . . ?
C34 C33 C32 120.8(4) . . ?
C35 C34 C33 121.5(4) . . ?
C34 C35 C36 119.4(4) . . ?
C35 C36 C31 120.3(4) . . ?
C42 S4 S3 106.26(12) . . ?
O41 C4 O42 123.5(3) . . ?
O41 C4 C41 119.6(3) . . ?
O42 C4 C41 116.9(3) . . ?
C46 C41 C42 118.8(3) . . ?
C46 C41 C4 116.5(3) . . ?
C42 C41 C4 124.7(3) . . ?
C43 C42 C41 119.2(3) . . ?
C43 C42 S4 121.4(3) . . ?
C41 C42 S4 119.4(3) . . ?
C44 C43 C42 120.9(4) . . ?
C43 C44 C45 120.3(4) . . ?
C46 C45 C44 119.1(4) . . ?
C45 C46 C41 121.8(4) . . ?
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
S1 C16 1.796(3) . ?
S1 S2 2.0399(12) . ?
O11 C1 1.311(4) . ?
O12 C1 1.208(4) . ?
C1 C11 1.476(5) . ?
C11 C12 1.389(5) . ?
C11 C16 1.407(5) . ?
C12 C13 1.363(6) . ?
C13 C14 1.371(6) . ?
C14 C15 1.378(6) . ?
C15 C16 1.388(5) . ?
S2 C26 1.792(4) . ?
O21 C2 1.243(4) . ?
O22 C2 1.287(4) . ?
C2 C21 1.487(5) . ?
C21 C22 1.385(5) . ?
C21 C26 1.409(5) . ?
C22 C23 1.372(6) . ?
C23 C24 1.382(6) . ?
C24 C25 1.373(6) . ?
C25 C26 1.390(5) . ?
S3 C32 1.794(4) . ?
S3 S4 2.0418(13) . ?
O31 C3 1.318(4) . ?
O32 C3 1.219(4) . ?
C3 C31 1.463(5) . ?
C31 C36 1.401(5) . ?
C31 C32 1.410(5) . ?
C32 C33 1.388(5) . ?
C33 C34 1.378(6) . ?
C34 C35 1.365(6) . ?
C35 C36 1.378(6) . ?
S4 C42 1.793(3) . ?
O41 C4 1.237(4) . ?
O42 C4 1.278(4) . ?
C4 C41 1.500(5) . ?
C41 C46 1.391(5) . ?
C41 C42 1.398(5) . ?
C42 C43 1.388(5) . ?
C43 C44 1.377(5) . ?
C44 C45 1.384(6) . ?
C45 C46 1.369(5) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30661107
