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#$Date: 2023-03-13 12:23:09 +0200 (Mon, 13 Mar 2023) $
#$Revision: 281840 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/69/8106928.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_8106928
loop_
_publ_author_name
'Mabkhot, Yahia N.'
'Barakat, Assem'
'Al-Showiman, Salim S.'
'Frey, Wolfgang'
'Uzzaman, Shams'
'Ghabbour, Hazem A.'
_publ_section_title
;
 Crystal structure of
 diethyl-3-methyl-4-phenylthieno[2,3-b]thiophene-2,5-dicarboxylate,
 C19H18O4S2
;
_journal_issue                   2
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              521
_journal_page_last               523
_journal_paper_doi               10.1515/ncrs-2015-0174
_journal_volume                  231
_journal_year                    2016
_chemical_formula_moiety         'C19 H17.75 O4.13 S2'
_chemical_formula_sum            'C19 H17.75 O4.13 S2'
_chemical_formula_weight         376.20
_chemical_name_systematic
; 
 'Compound Y11' 
;
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 92.681(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.1921(6)
_cell_length_b                   18.6304(14)
_cell_length_c                   13.3739(11)
_cell_measurement_reflns_used    2809
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.33
_cell_measurement_theta_min      1.88
_cell_volume                     1790.0(2)
_computing_cell_refinement       'Bruker APEXII Software Suite, 2008'
_computing_data_collection       'Bruker APEXII Software Suite, 2008'
_computing_data_reduction        'Bruker APEXII Software Suite, 2008'
_computing_molecular_graphics    'SHELXTL-plus, XP (Sheldrick, 1991)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker Kappa APEXII Duo'
_diffrn_measurement_method       'Omega + Phi Scans'
_diffrn_radiation_monochromator  Triumph
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0647
_diffrn_reflns_av_sigmaI/netI    0.0843
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            16128
_diffrn_reflns_theta_full        28.33
_diffrn_reflns_theta_max         28.33
_diffrn_reflns_theta_min         1.88
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.319
_exptl_absorpt_correction_T_max  0.9959
_exptl_absorpt_correction_T_min  0.9197
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'SADABS (Bruker, 2008)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.396
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             787
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.414
_refine_diff_density_min         -0.335
_refine_diff_density_rms         0.075
_refine_ls_extinction_coef       0.0010(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     311
_refine_ls_number_reflns         4455
_refine_ls_number_restraints     8
_refine_ls_restrained_S_all      1.016
_refine_ls_R_factor_all          0.0990
_refine_ls_R_factor_gt           0.0478
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0310P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0819
_refine_ls_wR_factor_ref         0.0913
_reflns_number_gt                2809
_reflns_number_total             4455
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            suppl_ncrs-2015-0174_suppl.cif
_cod_data_source_block           bak17
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               8106928
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 0.28487(7) 1.05569(3) 1.06346(4) 0.01667(14) Uani 1 1 d . . .
O1 O 0.2209(2) 0.91872(8) 1.28196(11) 0.0253(4) Uani 1 1 d . . .
C1 C 0.2400(3) 0.97373(10) 1.12131(16) 0.0146(5) Uani 1 1 d . . .
S2 S 0.26054(8) 1.04872(3) 0.82988(4) 0.01738(14) Uani 1 1 d . . .
O2 O 0.2822(2) 1.03710(7) 1.26938(11) 0.0206(4) Uani 1 1 d . . .
C2 C 0.2049(3) 0.91838(11) 1.05464(16) 0.0162(5) Uani 1 1 d . D .
O3 O 0.2296(2) 1.00775(8) 0.61769(12) 0.0264(4) Uani 1 1 d . . .
C3 C 0.2152(3) 0.94317(11) 0.95359(15) 0.0136(4) Uani 1 1 d . . .
O4 O 0.1773(2) 0.88993(8) 0.64215(11) 0.0227(4) Uani 1 1 d . . .
C4 C 0.2538(3) 1.01596(10) 0.94871(15) 0.0135(4) Uani 1 1 d . . .
C5 C 0.1946(3) 0.91198(10) 0.85588(16) 0.0146(5) Uani 1 1 d . . .
C6 C 0.2144(3) 0.96296(10) 0.78269(16) 0.0144(5) Uani 1 1 d . . .
C7 C 0.1545(4) 0.84275(13) 1.0831(2) 0.0265(6) Uani 1 1 d D . .
H7A H 0.058(4) 0.8227(15) 1.032(2) 0.038(8) Uiso 0.88 1 d P A 1
H7B H 0.275(4) 0.8184(17) 1.093(2) 0.035(10) Uiso 0.88 1 d P B 1
H7C H 0.112(4) 0.8418(16) 1.154(2) 0.037(9) Uiso 0.88 1 d P C 1
O5 O 0.0290(16) 0.8132(7) 1.1185(11) 0.031(3) Uani 0.13 1 d PDU D 2
H7D H 0.23(3) 0.804(8) 1.057(16) 0.037 Uiso 0.13 1 d PD E 2
C8 C 0.1615(3) 0.83373(11) 0.83866(15) 0.0169(5) Uani 1 1 d . . .
C9 C 0.3074(4) 0.78561(12) 0.85015(18) 0.0258(6) Uani 1 1 d . . .
H9 H 0.435(3) 0.8053(11) 0.8639(15) 0.023(6) Uiso 1 1 d . . .
C10 C 0.2754(4) 0.71185(13) 0.84042(19) 0.0316(6) Uani 1 1 d . . .
H10 H 0.377(4) 0.6812(14) 0.8476(19) 0.050(8) Uiso 1 1 d . . .
C11 C 0.0967(4) 0.68709(13) 0.82068(18) 0.0292(6) Uani 1 1 d . . .
H11 H 0.076(3) 0.6374(12) 0.8148(16) 0.026(6) Uiso 1 1 d . . .
C12 C -0.0480(4) 0.73479(12) 0.80665(18) 0.0267(6) Uani 1 1 d . . .
H12 H -0.173(4) 0.7169(13) 0.7930(18) 0.041(8) Uiso 1 1 d . . .
C13 C -0.0163(3) 0.80805(12) 0.81549(17) 0.0214(5) Uani 1 1 d . . .
H13 H -0.123(3) 0.8415(12) 0.8064(16) 0.027(6) Uiso 1 1 d . . .
C14 C 0.2456(3) 0.97125(11) 1.23066(16) 0.0171(5) Uani 1 1 d . . .
C15 C 0.2938(4) 1.04217(13) 1.37857(17) 0.0223(5) Uani 1 1 d . . .
H15A H 0.175(3) 1.0246(11) 1.4059(16) 0.028(7) Uiso 1 1 d . . .
H15B H 0.397(3) 1.0155(10) 1.4013(14) 0.010(5) Uiso 1 1 d . . .
C16 C 0.3236(4) 1.12014(14) 1.4034(2) 0.0289(6) Uani 1 1 d . . .
H16A H 0.222(4) 1.1513(13) 1.3809(18) 0.042(8) Uiso 1 1 d . . .
H16B H 0.336(4) 1.1266(13) 1.473(2) 0.046(8) Uiso 1 1 d . . .
H16C H 0.440(3) 1.1400(12) 1.3701(18) 0.037(7) Uiso 1 1 d . . .
C17 C 0.2085(3) 0.95719(12) 0.67298(17) 0.0189(5) Uani 1 1 d . . .
C18 C 0.1747(4) 0.87610(13) 0.53448(17) 0.0250(6) Uani 1 1 d . . .
H18A H 0.060(3) 0.8994(10) 0.5011(15) 0.016(6) Uiso 1 1 d . . .
H18B H 0.292(3) 0.8993(11) 0.5054(16) 0.024(6) Uiso 1 1 d . . .
C19 C 0.1728(4) 0.79585(15) 0.5246(2) 0.0323(6) Uani 1 1 d . . .
H19A H 0.065(4) 0.7741(13) 0.5535(18) 0.036(7) Uiso 1 1 d . . .
H19B H 0.175(3) 0.7803(14) 0.455(2) 0.047(8) Uiso 1 1 d . . .
H19C H 0.282(4) 0.7706(15) 0.562(2) 0.059(9) 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'
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
C4 S1 C1 90.00(10) . .
C2 C1 C14 128.24(19) . .
C2 C1 S1 113.51(16) . .
C14 C1 S1 118.25(15) . .
C4 S2 C6 89.78(10) . .
C14 O2 C15 116.25(17) . .
C1 C2 C3 110.66(19) . .
C1 C2 C7 125.1(2) . .
C3 C2 C7 124.2(2) . .
C4 C3 C5 111.51(18) . .
C4 C3 C2 112.26(18) . .
C5 C3 C2 136.23(19) . .
C17 O4 C18 117.63(18) . .
C3 C4 S2 114.11(16) . .
C3 C4 S1 113.54(15) . .
S2 C4 S1 132.35(12) . .
C6 C5 C3 111.06(18) . .
C6 C5 C8 125.81(19) . .
C3 C5 C8 123.10(18) . .
C5 C6 C17 131.34(19) . .
C5 C6 S2 113.53(16) . .
C17 C6 S2 115.10(15) . .
O5 C7 C2 137.5(7) . .
O5 C7 H7A 65.4(16) . .
C2 C7 H7A 109.8(16) . .
O5 C7 H7B 115(2) . .
C2 C7 H7B 104.1(19) . .
H7A C7 H7B 119(2) . .
O5 C7 H7C 48.9(16) . .
C2 C7 H7C 109.8(17) . .
H7A C7 H7C 113(2) . .
H7B C7 H7C 100(2) . .
O5 C7 H7D 105(10) . .
C2 C7 H7D 117(10) . .
H7A C7 H7D 83(10) . .
H7B C7 H7D 37(10) . .
H7C C7 H7D 121(10) . .
C7 O5 H7A 50.9(14) . .
C7 O5 H7C 56(2) . .
H7A O5 H7C 106(2) . .
C9 C8 C13 119.2(2) . .
C9 C8 C5 120.1(2) . .
C13 C8 C5 120.64(19) . .
C8 C9 C10 120.4(2) . .
C8 C9 H9 117.9(12) . .
C10 C9 H9 121.7(12) . .
C11 C10 C9 119.6(2) . .
C11 C10 H10 122.4(16) . .
C9 C10 H10 117.9(17) . .
C12 C11 C10 120.2(2) . .
C12 C11 H11 120.4(14) . .
C10 C11 H11 119.4(14) . .
C11 C12 C13 120.3(2) . .
C11 C12 H12 119.6(15) . .
C13 C12 H12 120.1(15) . .
C8 C13 C12 120.3(2) . .
C8 C13 H13 120.7(13) . .
C12 C13 H13 119.0(13) . .
O1 C14 O2 123.1(2) . .
O1 C14 C1 126.4(2) . .
O2 C14 C1 110.50(18) . .
O2 C15 C16 106.5(2) . .
O2 C15 H15A 109.5(13) . .
C16 C15 H15A 110.6(13) . .
O2 C15 H15B 107.4(12) . .
C16 C15 H15B 109.8(12) . .
H15A C15 H15B 112.9(18) . .
C15 C16 H16A 114.3(15) . .
C15 C16 H16B 110.4(16) . .
H16A C16 H16B 105(2) . .
C15 C16 H16C 111.1(13) . .
H16A C16 H16C 106(2) . .
H16B C16 H16C 110(2) . .
O3 C17 O4 124.4(2) . .
O3 C17 C6 123.6(2) . .
O4 C17 C6 111.93(18) . .
O4 C18 C19 105.2(2) . .
O4 C18 H18A 109.3(12) . .
C19 C18 H18A 112.5(11) . .
O4 C18 H18B 108.8(12) . .
C19 C18 H18B 112.7(12) . .
H18A C18 H18B 108.3(17) . .
C18 C19 H19A 112.7(14) . .
C18 C19 H19B 112.2(15) . .
H19A C19 H19B 108(2) . .
C18 C19 H19C 114.1(16) . .
H19A C19 H19C 103(2) . .
H19B C19 H19C 107(2) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 C4 1.709(2) .
S1 C1 1.749(2) .
O1 C14 1.213(2) .
C1 C2 1.379(3) .
C1 C14 1.462(3) .
S2 C4 1.705(2) .
S2 C6 1.744(2) .
O2 C14 1.353(2) .
O2 C15 1.462(3) .
C2 C3 1.433(3) .
C2 C7 1.508(3) .
O3 C17 1.211(2) .
C3 C4 1.386(3) .
C3 C5 1.432(3) .
O4 C17 1.335(2) .
O4 C18 1.462(3) .
C5 C6 1.376(3) .
C5 C8 1.493(3) .
C6 C17 1.470(3) .
C7 O5 1.176(8) .
C7 H7A 1.02(3) .
C7 H7B 0.98(3) .
C7 H7C 1.02(3) .
C7 H7D 0.98(2) .
O5 H7A 1.19(3) .
O5 H7C 0.92(3) .
C8 C9 1.383(3) .
C8 C13 1.387(3) .
C9 C10 1.398(3) .
C9 H9 1.00(2) .
C10 C11 1.379(4) .
C10 H10 0.93(3) .
C11 C12 1.374(3) .
C11 H11 0.94(2) .
C12 C13 1.388(3) .
C12 H12 0.97(3) .
C13 H13 0.99(2) .
C15 C16 1.503(3) .
C15 H15A 1.00(2) .
C15 H15B 0.93(2) .
C16 H16A 0.97(3) .
C16 H16B 0.94(3) .
C16 H16C 1.03(3) .
C18 C19 1.501(3) .
C18 H18A 1.02(2) .
C18 H18B 1.04(2) .
C19 H19A 0.97(3) .
C19 H19B 0.98(3) .
C19 H19C 1.03(3) .
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
C4 S1 C1 C2 0.68(17) . . . .
C4 S1 C1 C14 -179.98(16) . . . .
C14 C1 C2 C3 -179.10(19) . . . .
S1 C1 C2 C3 0.2(2) . . . .
C14 C1 C2 C7 3.3(4) . . . .
S1 C1 C2 C7 -177.44(19) . . . .
C1 C2 C3 C4 -1.2(2) . . . .
C7 C2 C3 C4 176.4(2) . . . .
C1 C2 C3 C5 179.3(2) . . . .
C7 C2 C3 C5 -3.0(4) . . . .
C5 C3 C4 S2 1.5(2) . . . .
C2 C3 C4 S2 -178.12(14) . . . .
C5 C3 C4 S1 -178.65(14) . . . .
C2 C3 C4 S1 1.7(2) . . . .
C6 S2 C4 C3 -0.93(16) . . . .
C6 S2 C4 S1 179.24(17) . . . .
C1 S1 C4 C3 -1.38(16) . . . .
C1 S1 C4 S2 178.45(16) . . . .
C4 C3 C5 C6 -1.4(2) . . . .
C2 C3 C5 C6 178.1(2) . . . .
C4 C3 C5 C8 176.99(19) . . . .
C2 C3 C5 C8 -3.5(4) . . . .
C3 C5 C6 C17 178.7(2) . . . .
C8 C5 C6 C17 0.4(4) . . . .
C3 C5 C6 S2 0.7(2) . . . .
C8 C5 C6 S2 -177.61(17) . . . .
C4 S2 C6 C5 0.12(17) . . . .
C4 S2 C6 C17 -178.25(16) . . . .
C1 C2 C7 O5 67.3(13) . . . .
C3 C2 C7 O5 -109.9(13) . . . .
C6 C5 C8 C9 100.7(3) . . . .
C3 C5 C8 C9 -77.4(3) . . . .
C6 C5 C8 C13 -82.3(3) . . . .
C3 C5 C8 C13 99.6(2) . . . .
C13 C8 C9 C10 -1.2(3) . . . .
C5 C8 C9 C10 175.9(2) . . . .
C8 C9 C10 C11 -0.9(4) . . . .
C9 C10 C11 C12 2.6(4) . . . .
C10 C11 C12 C13 -2.1(4) . . . .
C9 C8 C13 C12 1.7(3) . . . .
C5 C8 C13 C12 -175.4(2) . . . .
C11 C12 C13 C8 -0.1(3) . . . .
C15 O2 C14 O1 1.0(3) . . . .
C15 O2 C14 C1 -179.34(17) . . . .
C2 C1 C14 O1 0.5(4) . . . .
S1 C1 C14 O1 -178.71(18) . . . .
C2 C1 C14 O2 -179.2(2) . . . .
S1 C1 C14 O2 1.6(2) . . . .
C14 O2 C15 C16 -176.71(19) . . . .
C18 O4 C17 O3 2.2(3) . . . .
C18 O4 C17 C6 -177.89(18) . . . .
C5 C6 C17 O3 -179.6(2) . . . .
S2 C6 C17 O3 -1.6(3) . . . .
C5 C6 C17 O4 0.4(3) . . . .
S2 C6 C17 O4 178.42(14) . . . .
C17 O4 C18 C19 169.8(2) . . . .
