#------------------------------------------------------------------------------
#$Date: 2019-09-06 10:12:55 +0300 (Fri, 06 Sep 2019) $
#$Revision: 218035 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/36/7233684.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_7233684
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         'C22 H18 N4 O6 S2'
_chemical_formula_sum            'C22 H18 N4 O6 S2'
_chemical_formula_weight         498.52
_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                 108.108(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   14.1494(7)
_cell_length_b                   5.0861(2)
_cell_length_c                   15.1825(7)
_cell_measurement_reflns_used    4858
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      66.8407
_cell_measurement_theta_min      3.0598
_cell_volume                     1038.50(9)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug  3 2011,13:03:54)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug  3 2011,13:03:54)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug  3 2011,13:03:54)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      123(2)
_diffrn_detector_area_resol_mean 10.3389
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Xcalibur, Ruby, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_source         'Enhance Ultra (Cu) X-ray Source'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0229
_diffrn_reflns_av_sigmaI/netI    0.0153
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            9925
_diffrn_reflns_theta_full        66.95
_diffrn_reflns_theta_max         66.95
_diffrn_reflns_theta_min         3.73
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.782
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.76971
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug  3 2011,13:03:54)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.594
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             516
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.282
_refine_diff_density_min         -0.237
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     156
_refine_ls_number_reflns         1841
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0330
_refine_ls_R_factor_gt           0.0299
_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)+(0.0437P)²+0.5966P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0783
_refine_ls_wR_factor_ref         0.0803
_reflns_number_gt                1691
_reflns_number_total             1841
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            J-Mater-Chem-C-2014-2-3895-1.cif
_cod_data_source_block           mx59_13
_cod_original_cell_volume        1038.50(8)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7233684
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 0.52973(3) 0.19949(7) 0.60728(2) 0.01744(14) Uani 1 1 d . . .
O1 O 0.31493(8) -0.3220(2) 0.80685(8) 0.0212(3) Uani 1 1 d . . .
O2 O 0.58966(9) -0.8250(2) 0.92657(8) 0.0255(3) Uani 1 1 d . . .
O3 O 0.61020(8) -0.1646(2) 0.73271(8) 0.0250(3) Uani 1 1 d . . .
N1 N 0.45126(10) -0.5740(3) 0.86633(9) 0.0180(3) Uani 1 1 d . . .
N2 N 0.59980(10) -0.4942(3) 0.82976(9) 0.0191(3) Uani 1 1 d . . .
C1 C 0.47236(12) 0.4337(3) 0.52649(10) 0.0169(3) Uani 1 1 d . . .
C2 C 0.37387(12) 0.4687(3) 0.52081(11) 0.0203(3) Uani 1 1 d . . .
H2 H 0.3306 0.5898 0.4800 0.024 Uiso 1 1 calc R . .
C3 C 0.34510(12) 0.3058(3) 0.58195(11) 0.0194(3) Uani 1 1 d . . .
H3 H 0.2799 0.3058 0.5870 0.023 Uiso 1 1 calc R . .
C4 C 0.42072(12) 0.1433(3) 0.63478(11) 0.0173(3) Uani 1 1 d . . .
C5 C 0.40181(11) -0.0369(3) 0.69919(10) 0.0164(3) Uani 1 1 d . . .
H5 H 0.3357 -0.0233 0.7017 0.020 Uiso 1 1 calc R . .
C6 C 0.45533(11) -0.2241(3) 0.75808(10) 0.0163(3) Uani 1 1 d . . .
C7 C 0.40047(11) -0.3708(3) 0.81061(10) 0.0164(3) Uani 1 1 d . . .
C8 C 0.54918(12) -0.6438(3) 0.87713(11) 0.0185(3) Uani 1 1 d . . .
C9 C 0.55915(11) -0.2855(3) 0.77092(10) 0.0173(3) Uani 1 1 d . . .
C10 C 0.39545(13) -0.7276(3) 0.91595(12) 0.0234(4) Uani 1 1 d . . .
H10A H 0.4406 -0.8501 0.9587 0.035 Uiso 1 1 calc R . .
H10B H 0.3425 -0.8267 0.8712 0.035 Uiso 1 1 calc R . .
H10C H 0.3661 -0.6083 0.9510 0.035 Uiso 1 1 calc R . .
C11 C 0.70329(12) -0.5707(4) 0.84156(12) 0.0265(4) Uani 1 1 d . . .
H11A H 0.7292 -0.4651 0.8002 0.040 Uiso 1 1 calc R . .
H11B H 0.7057 -0.7574 0.8264 0.040 Uiso 1 1 calc R . .
H11C H 0.7439 -0.5404 0.9059 0.040 Uiso 1 1 calc R . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
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'
N N 0.0311 0.0180 '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'
S S 0.3331 0.5567 '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 91.58(7) . .
C7 N1 C8 124.84(13) . .
C7 N1 C10 116.66(13) . .
C8 N1 C10 118.50(13) . .
C8 N2 C9 125.00(13) . .
C8 N2 C11 116.47(13) . .
C9 N2 C11 118.50(13) . .
C2 C1 C1 127.80(18) . 3_666
C2 C1 S1 112.15(11) . .
C1 C1 S1 120.05(16) 3_666 .
C1 C2 C3 112.28(14) . .
C4 C3 C2 113.87(14) . .
C3 C4 C5 120.18(14) . .
C3 C4 S1 110.11(11) . .
C5 C4 S1 129.71(12) . .
C6 C5 C4 135.63(14) . .
C5 C6 C9 124.75(14) . .
C5 C6 C7 115.41(14) . .
C9 C6 C7 119.84(14) . .
O1 C7 N1 119.95(14) . .
O1 C7 C6 123.54(14) . .
N1 C7 C6 116.51(14) . .
O2 C8 N2 121.07(15) . .
O2 C8 N1 121.91(14) . .
N2 C8 N1 117.02(14) . .
O3 C9 N2 120.04(14) . .
O3 C9 C6 123.29(14) . .
N2 C9 C6 116.67(13) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 C1 1.7215(15) .
S1 C4 1.7422(15) .
O1 C7 1.2193(19) .
O2 C8 1.214(2) .
O3 C9 1.2236(19) .
N1 C7 1.386(2) .
N1 C8 1.390(2) .
N1 C10 1.4738(19) .
N2 C8 1.389(2) .
N2 C9 1.391(2) .
N2 C11 1.471(2) .
C1 C2 1.381(2) .
C1 C1 1.451(3) 3_666
C2 C3 1.396(2) .
C3 C4 1.392(2) .
C4 C5 1.425(2) .
C5 C6 1.363(2) .
C6 C9 1.455(2) .
C6 C7 1.477(2) .
