#------------------------------------------------------------------------------
#$Date: 2018-07-31 05:13:51 +0300 (Tue, 31 Jul 2018) $
#$Revision: 209309 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/11/2021193.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_2021193
loop_
_publ_author_name
'Mao, Yimin'
'Zavalij, Peter Y.'
_publ_section_title
;
 Two furan-2,5-dicarboxylic acid solvates crystallized from
 dimethylformamide and dimethyl sulfoxide
;
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              986
_journal_page_last               990
_journal_paper_doi               10.1107/S2053229618010471
_journal_volume                  74
_journal_year                    2018
_chemical_formula_iupac          'C6 H4 O5, C2 H6 O S'
_chemical_formula_moiety         'C6 H4 O5, C2 H6 O S'
_chemical_formula_sum            'C8 H10 O6 S'
_chemical_formula_weight         234.22
_chemical_name_systematic
;
Furan-2,5-dicarboxylic acid dimethyl sulfoxide monosolvate
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           'SHELXL-2015 & ZCIF'
_cell_angle_alpha                80.5164(17)
_cell_angle_beta                 77.3664(17)
_cell_angle_gamma                63.8260(16)
_cell_formula_units_Z            2
_cell_length_a                   6.3129(8)
_cell_length_b                   6.9099(9)
_cell_length_c                   13.0901(17)
_cell_measurement_reflns_used    2660
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      28.2
_cell_measurement_theta_min      3.2
_cell_volume                     498.53(11)
_computing_cell_refinement
;
APEX2 and SAINT (Bruker, 2010)
;
_computing_data_collection
;
APEX2 (Bruker, 2010)
;
_computing_data_reduction
;
APEX2 and SAINT (Bruker, 2010)
;
_computing_molecular_graphics
;
OLEX2 (Dolomanov et al.,  2009), Mercury (Macrae et al.,
2008)
and Marvin (ChemAxon, 2018)
;
_computing_publication_material
;
APEX2 (Bruker, 2010),
SHELXL2015 (Sheldrick, 2015b),
PLATON (Spek, 2009) and
publCIF (Westrip, 2010)
;
_computing_structure_refinement
;
SHELXL2015 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXS2015 (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker SMART APEXII CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0179
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            2044
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.490
_diffrn_reflns_theta_min         1.599
_exptl_absorpt_coefficient_mu    0.331
_exptl_absorpt_correction_T_max  0.987
_exptl_absorpt_correction_T_min  0.847
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(TWINABS; Krause et al.,  2015)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.560
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             244
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.297
_refine_diff_density_min         -0.263
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     177
_refine_ls_number_reflns         2044
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.000
_refine_ls_R_factor_all          0.0267
_refine_ls_R_factor_gt           0.0244
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0057P)²+0.3718P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0506
_refine_ls_wR_factor_ref         0.0513
_reflns_number_gt                1894
_reflns_number_total             2044
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            qp3012sup1.cif
_cod_data_source_block           II
_cod_database_code               2021193
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.946
_shelx_estimated_absorpt_t_max   0.987
loop_
_space_group_symop_operation_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_occupancy
O O1 0.08991(17) 0.41577(17) 0.24448(8) 0.0214(2) Uani d 1
S S1 0.07863(6) 0.45030(6) 0.12667(3) 0.01795(9) Uani d 1
C C1 0.3126(3) 0.2149(3) 0.07023(13) 0.0224(3) Uani d 1
H H1A 0.460(3) 0.189(3) 0.0900(14) 0.028(5) Uiso d 1
H H1B 0.318(3) 0.244(3) -0.0039(15) 0.033(5) Uiso d 1
H H1C 0.270(3) 0.098(3) 0.0972(14) 0.028(5) Uiso d 1
C C2 0.1993(3) 0.6431(3) 0.07744(14) 0.0268(3) Uani d 1
H H2A 0.086(4) 0.777(3) 0.1041(16) 0.042(6) Uiso d 1
H H2B 0.218(3) 0.654(3) 0.0013(15) 0.030(5) Uiso d 1
H H2C 0.348(3) 0.596(3) 0.1017(14) 0.030(5) Uiso d 1
O O11 0.65361(18) 0.56009(17) 0.35203(8) 0.0218(2) Uani d 1
H H11 0.794(4) 0.518(3) 0.3177(17) 0.047(6) Uiso d 1
O O12 0.57910(18) 0.77573(17) 0.20352(8) 0.0245(2) Uani d 1
C C11 0.5112(2) 0.7081(2) 0.28978(11) 0.0184(3) Uani d 1
C C12 0.2568(2) 0.7818(2) 0.33674(11) 0.0180(3) Uani d 1
O O25 0.10056(17) 0.93437(16) 0.27591(8) 0.0183(2) Uani d 1
C C13 0.1377(3) 0.7310(2) 0.42851(12) 0.0220(3) Uani d 1
H H13 0.205(3) 0.635(3) 0.4811(14) 0.025(4) Uiso d 1
C C14 -0.1092(3) 0.8591(2) 0.42580(12) 0.0220(3) Uani d 1
H H14 -0.239(3) 0.861(3) 0.4763(14) 0.027(5) Uiso d 1
C C15 -0.1224(2) 0.9787(2) 0.33226(11) 0.0180(3) Uani d 1
C C16 -0.3208(2) 1.1374(2) 0.27925(11) 0.0186(3) Uani d 1
O O61 -0.53223(18) 1.17145(18) 0.33764(8) 0.0228(2) Uani d 1
H H61 -0.637(4) 1.248(3) 0.3064(16) 0.043(6) Uiso d 1
O O62 -0.29003(18) 1.22351(17) 0.19237(8) 0.0241(2) Uani d 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
O1 S1 C2 104.53(7)
O1 S1 C1 105.94(7)
C2 S1 C1 100.26(8)
S1 C1 H1A 109.8(10)
S1 C1 H1B 105.9(11)
H1A C1 H1B 111.5(15)
S1 C1 H1C 106.4(10)
H1A C1 H1C 110.4(14)
H1B C1 H1C 112.6(15)
S1 C2 H2A 106.7(12)
S1 C2 H2B 107.3(10)
H2A C2 H2B 110.4(15)
S1 C2 H2C 108.6(11)
H2A C2 H2C 111.1(16)
H2B C2 H2C 112.4(15)
C11 O11 H11 106.5(14)
O12 C11 O11 124.71(13)
O12 C11 C12 123.03(13)
O11 C11 C12 112.26(12)
C13 C12 O25 110.77(12)
C13 C12 C11 134.23(13)
O25 C12 C11 115.00(12)
C15 O25 C12 105.88(11)
C12 C13 C14 106.34(13)
C12 C13 H13 126.0(11)
C14 C13 H13 127.6(11)
C15 C14 C13 106.26(13)
C15 C14 H14 125.7(11)
C13 C14 H14 128.1(11)
C14 C15 O25 110.75(12)
C14 C15 C16 134.29(13)
O25 C15 C16 114.93(12)
O62 C16 O61 125.09(13)
O62 C16 C15 123.00(13)
O61 C16 C15 111.90(12)
C16 O61 H61 111.1(15)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 S1 1.5336(10)
S1 C2 1.7802(17)
S1 C1 1.7811(15)
C1 H1A 0.953(18)
C1 H1B 0.954(19)
C1 H1C 0.951(19)
C2 H2A 0.95(2)
C2 H2B 0.972(19)
C2 H2C 0.957(19)
O11 C11 1.3238(17)
O11 H11 0.84(2)
O12 C11 1.2118(17)
C11 C12 1.472(2)
C12 C13 1.353(2)
C12 O25 1.3667(16)
O25 C15 1.3633(17)
C13 C14 1.418(2)
C13 H13 0.908(17)
C14 C15 1.356(2)
C14 H14 0.930(18)
C15 C16 1.4732(19)
C16 O62 1.2115(18)
C16 O61 1.3256(17)
O61 H61 0.79(2)
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
O11 H11 O1 1_655 0.84(2) 1.78(2) 2.6279(14) 177(2) yes
O61 H61 O1 1_465 0.79(2) 1.87(2) 2.6587(15) 173(2) yes
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
O12 C11 C12 C13 179.01(16)
O11 C11 C12 C13 -0.5(2)
O12 C11 C12 O25 -0.3(2)
O11 C11 C12 O25 -179.78(12)
C13 C12 O25 C15 -0.05(16)
C11 C12 O25 C15 179.44(12)
O25 C12 C13 C14 0.00(17)
C11 C12 C13 C14 -179.34(16)
C12 C13 C14 C15 0.04(18)
C13 C14 C15 O25 -0.07(17)
C13 C14 C15 C16 178.07(16)
C12 O25 C15 C14 0.07(16)
C12 O25 C15 C16 -178.46(12)
C14 C15 C16 O62 -178.39(16)
O25 C15 C16 O62 -0.3(2)
C14 C15 C16 O61 1.2(2)
O25 C15 C16 O61 179.33(12)

_cod_database_fobs_code 2021193
