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#$Date: 2019-09-06 10:13:07 +0300 (Fri, 06 Sep 2019) $
#$Revision: 218036 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/36/7233685.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_7233685
loop_
_publ_author_name
'Ying Shu'
'Annabel Mikosch'
'Kevin N. Winzenberg'
'Peter Kemppinen'
'Christopher D. Easton'
'Ante Bilic'
'Craig M. Forsyth'
'Christopher J. Dunn'
'Th. Birendra Singh'
'Gavin E. Collis'
_publ_section_title
;
 N-Alkyl functionalized barbituric and thiobarbituric acid bithiophene
 derivatives for vacuum deposited n-channel OFETs
;
_journal_name_full               'Journal of Materials Chemistry C'
_journal_page_first              3895
_journal_page_last               3899
_journal_paper_doi               10.1039/C4TC00002A
_journal_volume                  2
_journal_year                    2014
_chemical_formula_moiety         'C26 H26 N4 O6 S2'
_chemical_formula_sum            'C26 H26 N4 O6 S2'
_chemical_formula_weight         554.63
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_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                 96.938(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   5.0394(3)
_cell_length_b                   27.5017(17)
_cell_length_c                   8.9894(6)
_cell_measurement_reflns_used    4819
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      30.10
_cell_measurement_theta_min      2.72
_cell_volume                     1236.74(13)
_computing_cell_refinement       'Bruker APEX2 v2012.2 (Bruker AXS, 2012)'
_computing_data_collection       'Bruker APEX2 v2012.2 (Bruker AXS, 2012)'
_computing_data_reduction        'Bruker APEX2 v2012.2 (Bruker AXS, 2012)'
_computing_molecular_graphics    X-Seed/POVRay
_computing_publication_material  CIFTAB
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      123(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Bruker X8 APEXII CCD'
_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  0.0232
_diffrn_reflns_av_sigmaI/netI    0.0288
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_k_min       -38
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            11858
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         30.23
_diffrn_reflns_theta_min         2.96
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.267
_exptl_absorpt_correction_T_max  0.746
_exptl_absorpt_correction_T_min  0.707
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS-2008/1 (Bruker AXS, 2008)'
_exptl_crystal_colour            purple
_exptl_crystal_density_diffrn    1.489
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             580
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.473
_refine_diff_density_min         -0.218
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         3643
_refine_ls_number_restraints     12
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0480
_refine_ls_R_factor_gt           0.0392
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0455P)²+0.6027P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0949
_refine_ls_wR_factor_ref         0.0994
_reflns_number_gt                3133
_reflns_number_total             3643
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            J-Mater-Chem-C-2014-2-3895-2.cif
_cod_data_source_block           mx118_12
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7233685
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_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 0.32298(6) 0.551150(11) 0.06339(4) 0.01514(9) Uani 1 1 d . . .
O1 O 1.1400(2) 0.57010(4) 0.53784(11) 0.0230(2) Uani 1 1 d . . .
O2 O 1.4024(6) 0.70488(11) 0.2994(3) 0.0256(6) Uani 0.647(5) 1 d P A 1
O2' O 1.3307(11) 0.71280(19) 0.3377(6) 0.0242(10) Uani 0.353(5) 1 d P A 2
O3 O 0.6877(7) 0.62200(13) 0.0727(4) 0.0213(6) Uani 0.647(5) 1 d P A 1
O3' O 0.6222(13) 0.6297(2) 0.1082(7) 0.0249(11) Uani 0.353(5) 1 d P A 2
N1 N 1.2618(2) 0.63840(4) 0.42517(13) 0.0197(2) Uani 1 1 d . . .
N2 N 1.0537(5) 0.66187(8) 0.1819(3) 0.0159(5) Uani 0.647(5) 1 d P A 1
N2' N 0.9650(9) 0.67232(15) 0.2292(5) 0.0185(10) Uani 0.353(5) 1 d P A 2
C1 C 0.1057(2) 0.50283(5) 0.06088(14) 0.0136(2) Uani 1 1 d . . .
C2 C 0.1631(3) 0.47293(5) 0.18415(15) 0.0168(3) Uani 1 1 d . . .
H2 H 0.0624 0.4448 0.2025 0.020 Uiso 1 1 calc R . .
C3 C 0.3857(3) 0.48882(5) 0.27810(15) 0.0166(2) Uani 1 1 d . . .
H3 H 0.4543 0.4722 0.3671 0.020 Uiso 1 1 calc R . .
C4 C 0.4990(2) 0.53131(5) 0.23011(14) 0.0143(2) Uani 1 1 d . . .
C5 C 0.7280(2) 0.55139(5) 0.31695(14) 0.0148(2) Uani 1 1 d . A .
H5 H 0.7885 0.5317 0.4011 0.018 Uiso 1 1 calc R . .
C6 C 0.8817(3) 0.59181(5) 0.30918(15) 0.0162(2) Uani 1 1 d . . .
C7 C 1.0999(3) 0.59803(5) 0.43220(15) 0.0162(3) Uani 1 1 d . A .
C8 C 1.2515(7) 0.67050(14) 0.3002(4) 0.0167(6) Uani 0.647(5) 1 d P A 1
C8' C 1.1903(14) 0.6773(3) 0.3327(8) 0.0178(12) Uani 0.353(5) 1 d P A 2
C9 C 0.8640(8) 0.62562(16) 0.1785(5) 0.0144(7) Uani 0.647(5) 1 d P A 1
C9' C 0.8051(16) 0.6305(3) 0.2101(9) 0.0175(13) Uani 0.353(5) 1 d P A 2
C10 C 1.4811(3) 0.64549(5) 0.54778(16) 0.0210(3) Uani 1 1 d . A .
H10A H 1.6196 0.6665 0.5118 0.025 Uiso 1 1 calc R . .
H10B H 1.5639 0.6136 0.5757 0.025 Uiso 1 1 calc R . .
C11 C 1.3867(4) 0.66839(8) 0.6850(2) 0.0400(4) Uani 1 1 d . . .
H11A H 1.5389 0.6725 0.7628 0.060 Uiso 1 1 calc R A .
H11B H 1.2527 0.6473 0.7226 0.060 Uiso 1 1 calc R . .
H11C H 1.3072 0.7002 0.6585 0.060 Uiso 1 1 calc R . .
C12 C 1.0453(5) 0.69380(9) 0.0498(3) 0.0221(6) Uani 0.647(5) 1 d P A 1
H12A H 0.9905 0.6744 -0.0415 0.026 Uiso 0.647(5) 1 calc PR A 1
H12B H 1.2272 0.7065 0.0429 0.026 Uiso 0.647(5) 1 calc PR A 1
C12' C 0.8963(9) 0.71354(17) 0.1262(6) 0.0288(13) Uani 0.353(5) 1 d PU A 2
H12C H 0.9586 0.7442 0.1766 0.035 Uiso 0.353(5) 1 calc PR A 2
H12D H 0.6996 0.7155 0.1023 0.035 Uiso 0.353(5) 1 calc PR A 2
C13 C 0.8558(5) 0.73591(10) 0.0550(3) 0.0312(7) Uani 0.647(5) 1 d P A 1
H13A H 0.8577 0.7558 -0.0354 0.047 Uiso 0.647(5) 1 calc PR A 1
H13B H 0.9117 0.7558 0.1438 0.047 Uiso 0.647(5) 1 calc PR A 1
H13C H 0.6746 0.7236 0.0600 0.047 Uiso 0.647(5) 1 calc PR A 1
C13' C 1.0197(12) 0.7085(3) -0.0158(8) 0.0433(16) Uani 0.353(5) 1 d PU A 2
H13D H 0.9691 0.7363 -0.0810 0.065 Uiso 0.353(5) 1 calc PR A 2
H13E H 0.9563 0.6784 -0.0668 0.065 Uiso 0.353(5) 1 calc PR A 2
H13F H 1.2147 0.7073 0.0072 0.065 Uiso 0.353(5) 1 calc PR A 2
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'
N N 0.0061 0.0033 '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
C1 S1 C4 91.52(6) . .
C8' N1 C7 122.6(3) . .
C7 N1 C8 124.56(19) . .
C8' N1 C10 117.8(3) . .
C7 N1 C10 117.64(11) . .
C8 N1 C10 117.39(19) . .
C9 N2 C8 124.9(3) . .
C9 N2 C12 117.4(2) . .
C8 N2 C12 117.6(2) . .
C8' N2' C9' 125.1(6) . .
C8' N2' C12' 117.1(4) . .
C9' N2' C12' 117.7(5) . .
C2 C1 C1 127.52(15) . 3_565
C2 C1 S1 112.19(9) . .
C1 C1 S1 120.29(13) 3_565 .
C1 C2 C3 112.05(12) . .
C2 C3 C4 114.00(12) . .
C3 C4 C5 119.43(12) . .
C3 C4 S1 110.23(9) . .
C5 C4 S1 130.35(10) . .
C6 C5 C4 135.79(12) . .
C5 C6 C9' 122.3(4) . .
C5 C6 C7 115.74(12) . .
C9' C6 C7 120.6(4) . .
C5 C6 C9 124.7(2) . .
C7 C6 C9 119.2(2) . .
O1 C7 N1 119.86(12) . .
O1 C7 C6 123.40(12) . .
N1 C7 C6 116.74(12) . .
O2 C8 N2 121.4(3) . .
O2 C8 N1 121.6(3) . .
N2 C8 N1 116.9(3) . .
O2' C8' N1 119.9(6) . .
O2' C8' N2' 122.4(7) . .
O3 C9 N2 120.8(4) . .
O3 C9 C6 122.0(4) . .
N2 C9 C6 117.2(3) . .
O3' C9' N2' 118.5(8) . .
O3' C9' C6 125.8(7) . .
N1 C10 C11 112.54(13) . .
N2 C12 C13 113.0(3) . .
N2' C12' C13' 111.9(6) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 C1 1.7204(13) .
S1 C4 1.7348(13) .
O1 C7 1.2191(16) .
O2 C8 1.214(5) .
O2' C8' 1.204(9) .
O3 C9 1.224(6) .
O3' C9' 1.219(11) .
N1 C8' 1.376(8) .
N1 C7 1.3840(17) .
N1 C8 1.425(4) .
N1 C10 1.4761(17) .
N2 C9 1.379(5) .
N2 C8 1.387(4) .
N2 C12 1.473(4) .
N2' C8' 1.384(8) .
N2' C9' 1.404(9) .
N2' C12' 1.478(6) .
C1 C2 1.3821(18) .
C1 C1 1.440(2) 3_565
C2 C3 1.3905(18) .
C3 C4 1.3917(18) .
C4 C5 1.4243(18) .
C5 C6 1.3615(18) .
C6 C9' 1.410(9) .
C6 C7 1.4722(18) .
C6 C9 1.493(5) .
C10 C11 1.512(2) .
C12 C13 1.505(4) .
C12' C13' 1.492(8) .
