#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/41/2234181.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_2234181
loop_
_publ_author_name
'Pop, Lucian C.'
'Preite, Marcelo'
'Manriquez, Juan Manuel'
'Vega, Andrés'
'Chavez, Ivonne'
_publ_section_title
;
 1,1':4',1''-Terphenyl-2',5'-dicarboxylic acid dimethyl
 sulfoxide-d₆ disolvate
;
_journal_coeditor_code           FY2045
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1192
_journal_paper_doi               10.1107/S1600536812012056
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C20 H14 O4, 2C2 D6 O S'
_chemical_formula_moiety         'C20 H14 O4, 2(C2 D6 O S)'
_chemical_formula_sum            'C24 H14 D12 O6 S2'
_chemical_formula_weight         486.61
_chemical_name_systematic
;
1,1':4',1''-Terphenyl-2',5'-dicarboxylic acid dimethyl sulfoxide-d₆
disolvate
;
_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                97.076(2)
_cell_angle_beta                 97.074(2)
_cell_angle_gamma                93.127(2)
_cell_formula_units_Z            1
_cell_length_a                   6.5184(9)
_cell_length_b                   8.8273(12)
_cell_length_c                   10.6017(14)
_cell_measurement_reflns_used    1643
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      24.206
_cell_measurement_theta_min      2.331
_cell_volume                     599.26(14)
_computing_cell_refinement       'SAINT-NT (Bruker, 1999)'
_computing_data_collection       'SMART-NT (Bruker, 2001)'
_computing_data_reduction        'SAINT-NT (Bruker, 1999)'
_computing_molecular_graphics    'SHELXTL-NT (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL-NT (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXTL-NT (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL-NT (Sheldrick, 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Siemens SMART CCD area-detector'
_diffrn_measurement_method       'φ and ω 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  0.0119
_diffrn_reflns_av_sigmaI/netI    0.0194
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            3730
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.33
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.259
_exptl_absorpt_correction_T_max  0.9746
_exptl_absorpt_correction_T_min  0.9287
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2001)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.348
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             250
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.530
_refine_diff_density_min         -0.168
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     148
_refine_ls_number_reflns         2101
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0590
_refine_ls_R_factor_gt           0.0491
_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)+(0.0891P)²+0.1414P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1357
_refine_ls_wR_factor_ref         0.1451
_reflns_number_gt                1707
_reflns_number_total             2101
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            fy2045.cif
_cod_data_source_block           I
_cod_database_code               2234181
_cod_database_fobs_code          2234181
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
C C1 0.6023(3) 0.3696(2) 0.48626(19) 0.0397(5) Uani d . 1 1
H H1 0.6737 0.2814 0.4770 0.048 Uiso calc R 1 1
C C2 0.6546(3) 0.4883(2) 0.41945(19) 0.0371(5) Uani d . 1 1
C C10 0.8077(3) 0.4593(2) 0.3263(2) 0.0408(5) Uani d . 1 1
O O1 0.9582(2) 0.37837(18) 0.36916(14) 0.0503(4) Uani d . 1 1
O O2 0.7903(3) 0.5003(2) 0.22114(16) 0.0603(5) Uani d . 1 1
H H10 1.0348 0.3461 0.3042 0.073(8) Uiso d . 1 1
C C3 0.5515(3) 0.6244(2) 0.43352(19) 0.0385(5) Uani d . 1 1
C C4 0.6018(3) 0.7627(2) 0.3727(2) 0.0413(5) Uani d . 1 1
C C5 0.4423(4) 0.8397(3) 0.3156(2) 0.0532(6) Uani d . 1 1
H H5 0.3059 0.8007 0.3118 0.064 Uiso calc R 1 1
C C6 0.4828(5) 0.9733(3) 0.2644(3) 0.0637(7) Uani d . 1 1
H H6 0.3746 1.0236 0.2265 0.076 Uiso calc R 1 1
C C7 0.6846(5) 1.0312(3) 0.2699(3) 0.0640(7) Uani d . 1 1
H H7 0.7132 1.1199 0.2343 0.077 Uiso calc R 1 1
C C8 0.8446(4) 0.9578(3) 0.3283(2) 0.0607(7) Uani d . 1 1
H H8 0.9807 0.9980 0.3329 0.073 Uiso calc R 1 1
C C9 0.8033(4) 0.8244(3) 0.3801(2) 0.0500(6) Uani d . 1 1
H H9 0.9118 0.7760 0.4200 0.060 Uiso calc R 1 1
S S1 0.18071(11) 0.35077(8) 0.07652(6) 0.0630(3) Uani d . 1 1
O O3 0.1731(3) 0.2709(3) 0.19405(18) 0.0834(7) Uani d . 1 1
C C11 0.4021(4) 0.2871(4) 0.0103(3) 0.0744(8) Uani d . 1 1
D D11A 0.5249 0.3310 0.0647 0.112 Uiso calc R 1 1
D D11B 0.4020 0.3183 -0.0733 0.112 Uiso calc R 1 1
D D11C 0.3993 0.1776 0.0035 0.112 Uiso calc R 1 1
C C12 -0.0093(5) 0.2526(4) -0.0412(3) 0.0850(10) Uani d . 1 1
D D12A 0.0088 0.1449 -0.0479 0.127 Uiso calc R 1 1
D D12B 0.0036 0.2878 -0.1222 0.127 Uiso calc R 1 1
D D12C -0.1442 0.2715 -0.0180 0.127 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'
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'
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
C2 C1 C3 . 2_666 123.41(19)
C2 C1 H1 . . 118.3
C3 C1 H1 2_666 . 118.3
C1 C2 C3 . . 119.46(18)
C1 C2 C10 . . 117.34(18)
C3 C2 C10 . . 122.99(19)
O2 C10 O1 . . 123.55(19)
O2 C10 C2 . . 123.75(19)
O1 C10 C2 . . 112.63(18)
C10 O1 H10 . . 110.50
C1 C3 C2 2_666 . 117.12(19)
C1 C3 C4 2_666 . 118.39(18)
C2 C3 C4 . . 124.45(18)
C9 C4 C5 . . 118.6(2)
C9 C4 C3 . . 121.63(19)
C5 C4 C3 . . 119.6(2)
C6 C5 C4 . . 121.2(2)
C6 C5 H5 . . 119.4
C4 C5 H5 . . 119.4
C7 C6 C5 . . 119.5(2)
C7 C6 H6 . . 120.2
C5 C6 H6 . . 120.2
C6 C7 C8 . . 120.1(2)
C6 C7 H7 . . 120.0
C8 C7 H7 . . 120.0
C7 C8 C9 . . 120.2(2)
C7 C8 H8 . . 119.9
C9 C8 H8 . . 119.9
C4 C9 C8 . . 120.4(2)
C4 C9 H9 . . 119.8
C8 C9 H9 . . 119.8
O3 S1 C12 . . 105.90(15)
O3 S1 C11 . . 105.11(13)
C12 S1 C11 . . 98.15(16)
S1 C11 D11A . . 109.5
S1 C11 D11B . . 109.5
D11A C11 D11B . . 109.5
S1 C11 D11C . . 109.5
D11A C11 D11C . . 109.5
D11B C11 D11C . . 109.5
S1 C12 D12A . . 109.5
S1 C12 D12B . . 109.5
D12A C12 D12B . . 109.5
S1 C12 D12C . . 109.5
D12A C12 D12C . . 109.5
D12B C12 D12C . . 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
C1 C2 . 1.385(3)
C1 C3 2_666 1.391(3)
C1 H1 . 0.9300
C2 C3 . 1.410(3)
C2 C10 . 1.498(3)
C10 O2 . 1.209(3)
C10 O1 . 1.314(3)
O1 H10 . 0.926
C3 C1 2_666 1.391(3)
C3 C4 . 1.489(3)
C4 C9 . 1.384(3)
C4 C5 . 1.390(3)
C5 C6 . 1.384(3)
C5 H5 . 0.9300
C6 C7 . 1.377(4)
C6 H6 . 0.9300
C7 C8 . 1.380(4)
C7 H7 . 0.9300
C8 C9 . 1.386(3)
C8 H8 . 0.9300
C9 H9 . 0.9300
S1 O3 . 1.5101(19)
S1 C12 . 1.754(3)
S1 C11 . 1.769(3)
C11 D11A . 0.9600
C11 D11B . 0.9600
C11 D11C . 0.9600
C12 D12A . 0.9600
C12 D12B . 0.9600
C12 D12C . 0.9600
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
O1 H10 O3 1_655 0.926 1.659 2.581(2) 174
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_site_symmetry_1
_geom_torsion_site_symmetry_4
_geom_torsion
C3 C1 C2 C3 2_666 . 1.1(3)
C3 C1 C2 C10 2_666 . -173.80(19)
C1 C2 C10 O2 . . 137.8(2)
C3 C2 C10 O2 . . -37.0(3)
C1 C2 C10 O1 . . -39.3(3)
C3 C2 C10 O1 . . 145.9(2)
C1 C2 C3 C1 . 2_666 -1.1(3)
C10 C2 C3 C1 . 2_666 173.57(18)
C1 C2 C3 C4 . . 176.46(19)
C10 C2 C3 C4 . . -8.9(3)
C1 C3 C4 C9 2_666 . 128.7(2)
C2 C3 C4 C9 . . -48.8(3)
C1 C3 C4 C5 2_666 . -46.1(3)
C2 C3 C4 C5 . . 136.4(2)
C9 C4 C5 C6 . . 1.4(4)
C3 C4 C5 C6 . . 176.4(2)
C4 C5 C6 C7 . . 0.0(4)
C5 C6 C7 C8 . . -1.2(4)
C6 C7 C8 C9 . . 0.9(4)
C5 C4 C9 C8 . . -1.8(3)
C3 C4 C9 C8 . . -176.6(2)
C7 C8 C9 C4 . . 0.6(4)
