#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/32/2233252.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_2233252
loop_
_publ_author_name
'Sun, Lili'
'Li, Guijuan'
'Su, Qing'
_publ_section_title
;
 3-[(2-Formylthiophen-3-yl)(hydroxy)methyl]thiophene-2-carbaldehyde
;
_journal_coeditor_code           MW2040
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o182
_journal_paper_doi               10.1107/S1600536811052500
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C11 H8 O3 S2'
_chemical_formula_moiety         'C11 H8 O3 S2'
_chemical_formula_sum            'C11 H8 O3 S2'
_chemical_formula_weight         252.29
_chemical_name_systematic
;
3-[(2-Formylthiophen-3-yl)(hydroxy)methyl]thiophene-2-carbaldehyde
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 101.998(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.6227(18)
_cell_length_b                   10.136(2)
_cell_length_c                   14.272(3)
_cell_measurement_reflns_used    2097
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.09
_cell_measurement_theta_min      2.48
_cell_volume                     1078.6(4)
_computing_cell_refinement       'SAINT (Bruker, 1998)'
_computing_data_collection       'SMART (Bruker, 1998)'
_computing_data_reduction        'SAINT (Bruker, 1998)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 9.00
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area-detector'
_diffrn_measurement_method       'phi and omega 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  0.0250
_diffrn_reflns_av_sigmaI/netI    0.0273
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            6687
_diffrn_reflns_theta_full        25.75
_diffrn_reflns_theta_max         26.09
_diffrn_reflns_theta_min         2.48
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.479
_exptl_absorpt_correction_T_max  0.9060
_exptl_absorpt_correction_T_min  0.8855
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2001)
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.554
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.305
_refine_diff_density_min         -0.172
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         2122
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0501
_refine_ls_R_factor_gt           0.0407
_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)+(0.0511P)²+0.3301P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0940
_refine_ls_wR_factor_ref         0.1000
_reflns_number_gt                1798
_reflns_number_total             2122
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            mw2040.cif
_cod_data_source_block           I
_cod_original_cell_volume        1078.7(4)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2233252
_cod_database_fobs_code          2233252
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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
S S1 0.18693(8) 0.05474(6) 0.40611(4) 0.0483(2) Uani d . 1 1
S S2 0.35779(8) 0.71529(6) 0.45073(4) 0.04438(19) Uani d . 1 1
O O1 0.2719(2) 0.41275(16) 0.18884(10) 0.0461(4) Uani d . 1 1
H H1 0.2189 0.3605 0.1490 0.069 Uiso d R 1 1
O O3 -0.0407(2) 0.72325(18) 0.41728(12) 0.0549(5) Uani d . 1 1
C C2 0.2269(3) 0.2727(2) 0.32022(14) 0.0333(5) Uani d . 1 1
O O2 -0.1559(2) 0.3386(2) 0.33753(15) 0.0696(6) Uani d . 1 1
C C1 0.1038(3) 0.2063(2) 0.36192(15) 0.0364(5) Uani d . 1 1
C C8 0.2905(3) 0.5135(2) 0.33862(14) 0.0328(5) Uani d . 1 1
C C11 0.0174(3) 0.6327(2) 0.37609(15) 0.0434(5) Uani d . 1 1
H H11 -0.0644 0.5759 0.3388 0.052 Uiso calc R 1 1
C C7 0.2056(3) 0.6090(2) 0.38216(14) 0.0356(5) Uani d . 1 1
C C5 -0.0793(3) 0.2385(3) 0.36692(18) 0.0480(6) Uani d . 1 1
H H5 -0.1425 0.1769 0.3951 0.058 Uiso calc R 1 1
C C9 0.4790(3) 0.5276(2) 0.36272(15) 0.0391(5) Uani d . 1 1
H H9 0.5582 0.4716 0.3407 0.047 Uiso calc R 1 1
C C4 0.3810(3) 0.0795(2) 0.36802(17) 0.0487(6) Uani d . 1 1
H H4 0.4740 0.0184 0.3759 0.058 Uiso calc R 1 1
C C6 0.1976(3) 0.4072(2) 0.27314(14) 0.0344(5) Uani d . 1 1
H H6 0.0688 0.4260 0.2560 0.041 Uiso calc R 1 1
C C10 0.5322(3) 0.6320(2) 0.42159(16) 0.0435(5) Uani d . 1 1
H H10 0.6517 0.6553 0.4436 0.052 Uiso calc R 1 1
C C3 0.3852(3) 0.1982(2) 0.32482(16) 0.0424(5) Uani d . 1 1
H H3 0.4825 0.2276 0.3006 0.051 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
C4 S1 C1 91.70(11)
C10 S2 C7 91.10(11)
C6 O1 H1 109.5
C1 C2 C3 111.6(2)
C1 C2 C6 125.23(18)
C3 C2 C6 123.17(19)
C2 C1 C5 131.0(2)
C2 C1 S1 111.02(16)
C5 C1 S1 117.75(17)
C7 C8 C9 111.52(19)
C7 C8 C6 125.27(18)
C9 C8 C6 123.21(19)
O3 C11 C7 123.5(2)
O3 C11 H11 118.2
C7 C11 H11 118.2
C8 C7 C11 130.1(2)
C8 C7 S2 111.65(15)
C11 C7 S2 118.27(17)
O2 C5 C1 125.2(2)
O2 C5 H5 117.4
C1 C5 H5 117.4
C10 C9 C8 112.8(2)
C10 C9 H9 123.6
C8 C9 H9 123.6
C3 C4 S1 112.42(18)
C3 C4 H4 123.8
S1 C4 H4 123.8
O1 C6 C8 106.03(16)
O1 C6 C2 111.10(17)
C8 C6 C2 111.21(16)
O1 C6 H6 109.5
C8 C6 H6 109.5
C2 C6 H6 109.5
C9 C10 S2 112.97(17)
C9 C10 H10 123.5
S2 C10 H10 123.5
C4 C3 C2 113.3(2)
C4 C3 H3 123.4
C2 C3 H3 123.4
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C4 1.698(3)
S1 C1 1.730(2)
S2 C10 1.698(2)
S2 C7 1.730(2)
O1 C6 1.434(2)
O1 H1 0.8200
O3 C11 1.222(3)
C2 C1 1.386(3)
C2 C3 1.414(3)
C2 C6 1.515(3)
O2 C5 1.201(3)
C1 C5 1.450(3)
C8 C7 1.383(3)
C8 C9 1.414(3)
C8 C6 1.503(3)
C11 C7 1.439(3)
C11 H11 0.9300
C5 H5 0.9300
C9 C10 1.359(3)
C9 H9 0.9300
C4 C3 1.355(3)
C4 H4 0.9300
C6 H6 0.9800
C10 H10 0.9300
C3 H3 0.9300
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
C6 H6 O2 . 0.98 2.43 3.101(3) 125 y
C11 H11 O2 . 0.93 2.50 3.261(3) 139 y
C4 H4 O1 2_645 0.93 2.55 3.377(3) 149 y
C9 H9 O2 1_655 0.93 2.57 3.458(3) 160 y
C10 H10 O3 1_655 0.93 2.55 3.397(3) 152 y
O1 H1 O3 2_545 0.82 2.03 2.825(2) 162 y
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
C3 C2 C1 C5 -174.3(2)
C6 C2 C1 C5 4.5(4)
C3 C2 C1 S1 0.4(2)
C6 C2 C1 S1 179.10(16)
C4 S1 C1 C2 -0.71(16)
C4 S1 C1 C5 174.72(19)
C9 C8 C7 C11 178.7(2)
C6 C8 C7 C11 -1.0(4)
C9 C8 C7 S2 0.6(2)
C6 C8 C7 S2 -179.07(15)
O3 C11 C7 C8 -178.5(2)
O3 C11 C7 S2 -0.5(3)
C10 S2 C7 C8 -0.24(17)
C10 S2 C7 C11 -178.60(18)
C2 C1 C5 O2 -4.2(4)
S1 C1 C5 O2 -178.5(2)
C7 C8 C9 C10 -0.8(3)
C6 C8 C9 C10 178.91(18)
C1 S1 C4 C3 0.90(19)
C7 C8 C6 O1 129.0(2)
C9 C8 C6 O1 -50.6(2)
C7 C8 C6 C2 -110.1(2)
C9 C8 C6 C2 70.2(2)
C1 C2 C6 O1 -141.08(19)
C3 C2 C6 O1 37.5(3)
C1 C2 C6 C8 101.1(2)
C3 C2 C6 C8 -80.3(2)
C8 C9 C10 S2 0.6(3)
C7 S2 C10 C9 -0.21(18)
S1 C4 C3 C2 -0.9(3)
C1 C2 C3 C4 0.3(3)
C6 C2 C3 C4 -178.46(19)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30657354
