#------------------------------------------------------------------------------
#$Date: 2016-02-20 05:06:23 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176774 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/53/2205302.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_2205302
loop_
_publ_author_name
'Nadia Malek'
'Thierry Maris'
'Michel Simard'
'James D. Wuest'
_publ_section_title
;
 Tetrakis(4-carboxyphenyl)methane--dimethyl sulfoxide--toluene (1/4/1)
;
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o518
_journal_page_last               o520
_journal_paper_doi               10.1107/S1600536805002485
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          'C29 H20 O8, C7 H8, 4C2 H6 O S'
_chemical_formula_moiety         'C29 H20 O8, C7 H8, 4C2 H6 O S'
_chemical_formula_sum            'C44 H52 O12 S4'
_chemical_formula_weight         901.10
_chemical_name_common
'Tetrakis(4-carboxyphenyl)methane--dimethyl sulfoxide--toluene (1/4/1)'
_chemical_name_systematic
;
4,4',4'',4'''-methanetetrayltetracarboxylic acid--dimethyl sulfoxide--toluene
(1/4/1)
;
_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                 123.61(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   28.723(15)
_cell_length_b                   7.269(5)
_cell_length_c                   26.824(9)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    225(2)
_cell_measurement_theta_max      21.0
_cell_measurement_theta_min      20.0
_cell_volume                     4664(5)
_computing_cell_refinement       'CAD-4 Software '
_computing_data_collection       'CAD-4 Software (Enraf--Nonius, 1989)'
_computing_data_reduction        'local Program'
_computing_molecular_graphics
'SHELXTL (Bruker, 1997) and ATOMS (Shape Software, 2002)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      225(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Enraf--Nonius CAD-4'
_diffrn_measurement_method       ω/2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Sealed tube'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.067
_diffrn_reflns_av_sigmaI/netI    0.0371
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            32349
_diffrn_reflns_theta_full        69.86
_diffrn_reflns_theta_max         69.86
_diffrn_reflns_theta_min         3.62
_diffrn_standards_decay_%        -3.90
_diffrn_standards_interval_time  60
_diffrn_standards_number         6
_exptl_absorpt_coefficient_mu    2.360
_exptl_absorpt_correction_T_max  0.87
_exptl_absorpt_correction_T_min  0.38
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   'from crystal shape'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.283
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1904
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.783
_refine_diff_density_min         -0.528
_refine_ls_extinction_coef       0.00030(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     295
_refine_ls_number_reflns         4410
_refine_ls_number_restraints     46
_refine_ls_restrained_S_all      1.012
_refine_ls_R_factor_all          0.0790
_refine_ls_R_factor_gt           0.0657
_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)+(0.136P)²] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1820
_refine_ls_wR_factor_ref         0.1903
_reflns_number_gt                3266
_reflns_number_total             4410
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            lh6355.cif
_cod_data_source_block           IV
_cod_depositor_comments
;
The following automatic conversions were performed:
'_exptl_absorpt_correction_type' value 'Gaussian' changed to 'gaussian'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'Gaussian' changed to
'gaussian' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               2205302
_cod_database_fobs_code          2205302
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_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_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
O11 0.13332(11) 0.6814(3) 0.16478(11) 0.0570(6) Uani d . 1 . . O
H11 0.1492 0.7689 0.1602 0.086 Uiso calc R 1 . . H
O12 0.15109(13) 0.8442(4) 0.24366(13) 0.0771(9) Uani d . 1 . . O
O21 0.18517(9) -0.3172(4) 0.47396(11) 0.0698(7) Uani d . 1 . . O
H21 0.2007 -0.4051 0.4973 0.105 Uiso calc R 1 . . H
O22 0.10910(10) -0.4599(4) 0.45441(13) 0.0855(10) Uani d . 1 . . O
C1 0.0000 0.1838(5) 0.2500 0.0302(7) Uani d S 1 . . C
C11 0.03599(9) 0.3131(3) 0.23829(11) 0.0304(5) Uani d . 1 . . C
C12 0.06745(10) 0.4493(3) 0.28079(11) 0.0352(5) Uani d . 1 . . C
H12 0.0676 0.4552 0.3159 0.042 Uiso calc R 1 . . H
C13 0.09833(11) 0.5753(3) 0.27201(12) 0.0370(6) Uani d . 1 . . C
H13 0.1195 0.6653 0.3012 0.044 Uiso calc R 1 . . H
C14 0.09827(10) 0.5695(3) 0.22038(12) 0.0361(6) Uani d . 1 . . C
C15 0.06710(11) 0.4352(4) 0.17792(12) 0.0387(6) Uani d . 1 . . C
H15 0.0669 0.4297 0.1428 0.046 Uiso calc R 1 . . H
C16 0.03610(11) 0.3085(4) 0.18691(12) 0.0361(5) Uani d . 1 . . C
H16 0.0150 0.2187 0.1576 0.043 Uiso calc R 1 . . H
C17 0.13020(12) 0.7133(4) 0.21115(14) 0.0454(7) Uani d . 1 . . C
C21 0.03653(9) 0.0542(3) 0.30335(10) 0.0300(5) Uani d . 1 . . C
C22 0.09488(10) 0.0563(4) 0.33732(11) 0.0365(6) Uani d . 1 . . C
H22 0.1136 0.1451 0.3292 0.044 Uiso calc R 1 . . H
C23 0.12562(10) -0.0693(4) 0.38261(11) 0.0390(6) Uani d . 1 . . C
H23 0.1649 -0.0647 0.4049 0.047 Uiso calc R 1 . . H
C24 0.09918(10) -0.2024(3) 0.39557(11) 0.0344(5) Uani d . 1 . . C
C25 0.04080(11) -0.2081(3) 0.36102(11) 0.0359(5) Uani d . 1 . . C
H25 0.0222 -0.2989 0.3686 0.043 Uiso calc R 1 . . H
C26 0.01041(10) -0.0830(3) 0.31628(11) 0.0354(5) Uani d . 1 . . C
H26 -0.0288 -0.0891 0.2937 0.042 Uiso calc R 1 . . H
C27 0.13093(12) -0.3395(4) 0.44343(12) 0.0431(6) Uani d . 1 . . C
S1 0.15401(4) 0.14047(12) 0.15068(4) 0.0577(3) Uani d . 1 . . S
O1 0.17682(11) -0.0384(3) 0.14387(12) 0.0618(7) Uani d . 1 . . O
C18 0.1552(3) 0.2920(7) 0.1005(3) 0.131(3) Uani d . 1 . . C
H18A 0.1272 0.2549 0.0598 0.197 Uiso calc R 1 . . H
H18B 0.1919 0.2892 0.1068 0.197 Uiso calc R 1 . . H
H18C 0.1472 0.4159 0.1072 0.197 Uiso calc R 1 . . H
C19 0.2065(2) 0.2339(7) 0.2186(2) 0.1067(18) Uani d . 1 . . C
H19A 0.2105 0.1618 0.2511 0.160 Uiso calc R 1 . . H
H19B 0.1970 0.3597 0.2215 0.160 Uiso calc R 1 . . H
H19C 0.2415 0.2325 0.2210 0.160 Uiso calc R 1 . . H
S2 0.21912(3) 0.30259(12) 0.57796(4) 0.0555(3) Uani d . 1 . . S
O2 0.24262(9) 0.4438(4) 0.55691(12) 0.0760(8) Uani d . 1 . . O
C28 0.1833(2) 0.1468(6) 0.5187(2) 0.0866(13) Uani d . 1 . . C
H28A 0.1491 0.2030 0.4865 0.130 Uiso calc R 1 . . H
H28B 0.1744 0.0371 0.5324 0.130 Uiso calc R 1 . . H
H28C 0.2067 0.1139 0.5043 0.130 Uiso calc R 1 . . H
C29 0.27735(18) 0.1653(8) 0.6290(3) 0.114(2) Uani d . 1 . . C
H29A 0.3021 0.2353 0.6652 0.171 Uiso calc R 1 . . H
H29B 0.2973 0.1289 0.6110 0.171 Uiso calc R 1 . . H
H29C 0.2645 0.0564 0.6390 0.171 Uiso calc R 1 . . H
C31 0.0188(4) 0.1043(10) 0.5031(4) 0.103(2) Uani d PGDU 0.50 A -1 C
C32 0.0203(4) -0.0464(13) 0.4722(4) 0.111(3) Uani d PGDU 0.50 A -1 C
H32 0.0378 -0.0364 0.4513 0.133 Uiso calc PR 0.50 A -1 H
C33 -0.0039(4) -0.2118(11) 0.4722(4) 0.127(3) Uani d PGDU 0.50 A -1 C
H33 -0.0029 -0.3138 0.4513 0.152 Uiso calc PR 0.50 A -1 H
C34 -0.0298(4) -0.2266(11) 0.5031(5) 0.124(4) Uani d PGDU 0.50 A -1 C
H34 -0.0462 -0.3384 0.5031 0.148 Uiso calc PR 0.50 A -1 H
C35 -0.0314(4) -0.0758(14) 0.5340(4) 0.110(3) Uani d PGDU 0.50 A -1 C
H35 -0.0489 -0.0858 0.5549 0.132 Uiso calc PR 0.50 A -1 H
C36 -0.0071(4) 0.0896(12) 0.5340(4) 0.101(3) Uani d PGDU 0.50 A -1 C
H36 -0.0082 0.1915 0.5550 0.121 Uiso calc PR 0.50 A -1 H
C37 0.0450(6) 0.283(2) 0.5028(6) 0.119(4) Uani d PDU 0.50 A -1 C
H37A 0.0210 0.3847 0.4981 0.178 Uiso calc PR 0.50 A -1 H
H37B 0.0499 0.2836 0.4698 0.178 Uiso calc PR 0.50 A -1 H
H37C 0.0811 0.2969 0.5402 0.178 Uiso calc PR 0.50 A -1 H
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 0.0181 0.0091 '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'
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
C17 O11 H11 . . 109.5
C27 O21 H21 . . 109.5
C21 C1 C21 2 . 104.6(3)
C21 C1 C11 2 2 111.75(13)
C21 C1 C11 . 2 111.69(13)
C21 C1 C11 2 . 111.69(13)
C21 C1 C11 . . 111.75(13)
C11 C1 C11 2 . 105.5(3)
C16 C11 C12 . . 118.3(2)
C16 C11 C1 . . 123.9(2)
C12 C11 C1 . . 117.8(2)
C13 C12 C11 . . 121.1(2)
C13 C12 H12 . . 119.5
C11 C12 H12 . . 119.5
C12 C13 C14 . . 120.3(2)
C12 C13 H13 . . 119.9
C14 C13 H13 . . 119.9
C13 C14 C15 . . 119.1(2)
C13 C14 C17 . . 118.8(2)
C15 C14 C17 . . 122.1(2)
C14 C15 C16 . . 120.5(2)
C14 C15 H15 . . 119.7
C16 C15 H15 . . 119.7
C11 C16 C15 . . 120.8(2)
C11 C16 H16 . . 119.6
C15 C16 H16 . . 119.6
O12 C17 O11 . . 123.9(3)
O12 C17 C14 . . 122.5(3)
O11 C17 C14 . . 113.6(2)
C22 C21 C26 . . 117.4(2)
C22 C21 C1 . . 123.6(2)
C26 C21 C1 . . 118.8(2)
C23 C22 C21 . . 121.3(2)
C23 C22 H22 . . 119.3
C21 C22 H22 . . 119.3
C22 C23 C24 . . 120.7(2)
C22 C23 H23 . . 119.7
C24 C23 H23 . . 119.7
C23 C24 C25 . . 118.5(2)
C23 C24 C27 . . 121.9(2)
C25 C24 C27 . . 119.6(2)
C26 C25 C24 . . 120.8(2)
C26 C25 H25 . . 119.6
C24 C25 H25 . . 119.6
C25 C26 C21 . . 121.4(2)
C25 C26 H26 . . 119.3
C21 C26 H26 . . 119.3
O22 C27 O21 . . 122.5(3)
O22 C27 C24 . . 123.3(3)
O21 C27 C24 . . 114.2(2)
O1 S1 C19 . . 106.3(2)
O1 S1 C18 . . 104.7(2)
C19 S1 C18 . . 100.6(3)
S1 C18 H18A . . 109.5
S1 C18 H18B . . 109.5
H18A C18 H18B . . 109.5
S1 C18 H18C . . 109.5
H18A C18 H18C . . 109.5
H18B C18 H18C . . 109.5
S1 C19 H19A . . 109.5
S1 C19 H19B . . 109.5
H19A C19 H19B . . 109.5
S1 C19 H19C . . 109.5
H19A C19 H19C . . 109.5
H19B C19 H19C . . 109.5
O2 S2 C28 . . 105.2(2)
O2 S2 C29 . . 104.36(18)
C28 S2 C29 . . 99.6(3)
S2 C28 H28A . . 109.5
S2 C28 H28B . . 109.5
H28A C28 H28B . . 109.5
S2 C28 H28C . . 109.5
H28A C28 H28C . . 109.5
H28B C28 H28C . . 109.5
S2 C29 H29A . . 109.5
S2 C29 H29B . . 109.5
H29A C29 H29B . . 109.5
S2 C29 H29C . . 109.5
H29A C29 H29C . . 109.5
H29B C29 H29C . . 109.5
C32 C31 C36 . . 120.0
C32 C31 C37 . . 119.7(9)
C36 C31 C37 . . 120.3(9)
C33 C32 C31 . . 120.0
C33 C32 H32 . . 120.0
C31 C32 H32 . . 120.0
C32 C33 C34 . . 120.0
C32 C33 H33 . . 120.0
C34 C33 H33 . . 120.0
C35 C34 C33 . . 120.0
C35 C34 H34 . . 120.0
C33 C34 H34 . . 120.0
C34 C35 C36 . . 120.0
C34 C35 H35 . . 120.0
C36 C35 H35 . . 120.0
C35 C36 C31 . . 120.0
C35 C36 H36 . . 120.0
C31 C36 H36 . . 120.0
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
O11 C17 . 1.316(3)
O11 H11 . 0.8300
O12 C17 . 1.203(4)
O21 C27 . 1.308(4)
O21 H21 . 0.8300
O22 C27 . 1.204(4)
C1 C21 2 1.541(3)
C1 C21 . 1.541(3)
C1 C11 2 1.552(3)
C1 C11 . 1.552(3)
C11 C16 . 1.380(3)
C11 C12 . 1.398(3)
C12 C13 . 1.383(3)
C12 H12 . 0.9400
C13 C14 . 1.385(4)
C13 H13 . 0.9400
C14 C15 . 1.387(4)
C14 C17 . 1.499(4)
C15 C16 . 1.392(3)
C15 H15 . 0.9400
C16 H16 . 0.9400
C21 C22 . 1.396(3)
C21 C26 . 1.402(3)
C22 C23 . 1.379(4)
C22 H22 . 0.9400
C23 C24 . 1.388(4)
C23 H23 . 0.9400
C24 C25 . 1.397(4)
C24 C27 . 1.475(4)
C25 C26 . 1.367(4)
C25 H25 . 0.9400
C26 H26 . 0.9400
S1 O1 . 1.512(2)
S1 C19 . 1.735(5)
S1 C18 . 1.755(5)
C18 H18A . 0.9700
C18 H18B . 0.9700
C18 H18C . 0.9700
C19 H19A . 0.9700
C19 H19B . 0.9700
C19 H19C . 0.9700
S2 O2 . 1.500(2)
S2 C28 . 1.748(5)
S2 C29 . 1.770(4)
C28 H28A . 0.9700
C28 H28B . 0.9700
C28 H28C . 0.9700
C29 H29A . 0.9700
C29 H29B . 0.9700
C29 H29C . 0.9700
C31 C32 . 1.3900
C31 C36 . 1.3900
C31 C37 . 1.507(15)
C32 C33 . 1.3900
C32 H32 . 0.9400
C33 C34 . 1.3900
C33 H33 . 0.9400
C34 C35 . 1.3900
C34 H34 . 0.9400
C35 C36 . 1.3900
C35 H35 . 0.9400
C36 H36 . 0.9400
C37 H37A . 0.9700
C37 H37B . 0.9700
C37 H37C . 0.9700
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
O11 H11 O1 1_565 0.83 1.78 2.608(3) 174
O21 H21 O2 1_545 0.83 1.76 2.574(3) 168
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
C21 C1 C11 C16 2 -1.5(3)
C21 C1 C11 C16 . 115.3(2)
C11 C1 C11 C16 2 -123.2(3)
C21 C1 C11 C12 2 174.4(2)
C21 C1 C11 C12 . -68.8(3)
C11 C1 C11 C12 2 52.79(17)
C16 C11 C12 C13 . -0.6(4)
C1 C11 C12 C13 . -176.8(2)
C11 C12 C13 C14 . 0.5(4)
C12 C13 C14 C15 . -0.3(4)
C12 C13 C14 C17 . 177.3(2)
C13 C14 C15 C16 . 0.3(4)
C17 C14 C15 C16 . -177.3(2)
C12 C11 C16 C15 . 0.5(4)
C1 C11 C16 C15 . 176.5(2)
C14 C15 C16 C11 . -0.4(4)
C13 C14 C17 O12 . -7.8(4)
C15 C14 C17 O12 . 169.8(3)
C13 C14 C17 O11 . 171.7(3)
C15 C14 C17 O11 . -10.7(4)
C21 C1 C21 C22 2 122.0(3)
C11 C1 C21 C22 2 -116.9(2)
C11 C1 C21 C22 . 1.0(3)
C21 C1 C21 C26 2 -53.07(18)
C11 C1 C21 C26 2 68.0(3)
C11 C1 C21 C26 . -174.1(2)
C26 C21 C22 C23 . -1.3(4)
C1 C21 C22 C23 . -176.5(2)
C21 C22 C23 C24 . 0.2(4)
C22 C23 C24 C25 . 1.1(4)
C22 C23 C24 C27 . 179.5(3)
C23 C24 C25 C26 . -1.3(4)
C27 C24 C25 C26 . -179.8(2)
C24 C25 C26 C21 . 0.2(4)
C22 C21 C26 C25 . 1.1(4)
C1 C21 C26 C25 . 176.5(2)
C23 C24 C27 O22 . -177.7(3)
C25 C24 C27 O22 . 0.7(5)
C23 C24 C27 O21 . 3.6(4)
C25 C24 C27 O21 . -178.0(3)
C36 C31 C32 C33 . 0.0
C37 C31 C32 C33 . -179.8(11)
C31 C32 C33 C34 . 0.0
C32 C33 C34 C35 . 0.0
C33 C34 C35 C36 . 0.0
C34 C35 C36 C31 . 0.0
C32 C31 C36 C35 . 0.0
C37 C31 C36 C35 . 179.8(11)
