#------------------------------------------------------------------------------
#$Date: 2016-03-24 03:17:34 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179622 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/86/4508613.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_4508613
loop_
_publ_author_name
'Pati, Palas Baran'
'Senanayak, Satyaprasad P.'
'Narayan, K. S.'
'Zade, Sanjio S.'
_publ_section_title
;
 Solution processable benzooxadiazole and benzothiadiazole based d-a-d
 molecules with chalcogenophene: field effect transistor study and
 structure property relationship.
;
_journal_issue                   23
_journal_name_full               'ACS applied materials & interfaces'
_journal_page_first              12460
_journal_page_last               12468
_journal_paper_doi               10.1021/am403559a
_journal_volume                  5
_journal_year                    2013
_chemical_formula_moiety         'C14 H8 N2 O S2'
_chemical_formula_sum            'C14 H8 N2 O S2'
_chemical_formula_weight         284.36
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   12.528(7)
_cell_length_b                   10.051(5)
_cell_length_c                   19.086(10)
_cell_measurement_reflns_used    1503
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      22.08
_cell_measurement_theta_min      2.68
_cell_volume                     2403(2)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.971
_diffrn_measured_fraction_theta_max 0.971
_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  0.1481
_diffrn_reflns_av_sigmaI/netI    0.0797
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            16652
_diffrn_reflns_theta_full        24.59
_diffrn_reflns_theta_max         24.59
_diffrn_reflns_theta_min         2.13
_exptl_absorpt_coefficient_mu    0.433
_exptl_absorpt_correction_T_max  0.916
_exptl_absorpt_correction_T_min  0.896
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'sadabs, bruker, 2008'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.572
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1168
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.20
_refine_diff_density_max         3.200
_refine_diff_density_min         -1.206
_refine_diff_density_rms         0.252
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.704
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     131
_refine_ls_number_reflns         1967
_refine_ls_number_restraints     5
_refine_ls_restrained_S_all      1.734
_refine_ls_R_factor_all          0.1961
_refine_ls_R_factor_gt           0.1544
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.2000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3891
_refine_ls_wR_factor_ref         0.4355
_reflns_number_gt                1340
_reflns_number_total             2023
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            am403559a_si_002.cif
_cod_data_source_block           tot_3
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_database_code               4508613
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'
'-x, -y, -z'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'
'x-1/2, y, -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
C1 C 0.3819(8) 0.7710(9) -0.0263(5) 0.0181(13) Uani 1 1 d .
H1 H 0.4219 0.8336 -0.0508 0.022 Uiso 1 1 calc R
C2 C 0.2757(9) 0.7602(9) -0.0321(4) 0.0181(13) Uani 1 1 d .
H2 H 0.2373 0.8143 -0.0626 0.022 Uiso 1 1 calc R
C3 C 0.2226(9) 0.6608(9) 0.0110(5) 0.0181(13) Uani 1 1 d .
H3 H 0.1499 0.6431 0.0141 0.022 Uiso 1 1 calc R
C4 C 0.3122(9) 0.5938(9) 0.0492(5) 0.0181(13) Uani 1 1 d .
C5 C 0.3035(8) 0.4869(10) 0.1010(5) 0.017(2) Uani 1 1 d .
C6 C 0.3881(8) 0.4164(10) 0.1257(5) 0.019(2) Uani 1 1 d .
H6 H 0.4554 0.4365 0.1080 0.022 Uiso 1 1 calc R
C7 C 0.3800(7) 0.3129(10) 0.1773(5) 0.016(2) Uani 1 1 d .
H7 H 0.4424 0.2722 0.1927 0.019 Uiso 1 1 calc R
C8 C 0.2847(7) 0.2712(8) 0.2050(4) 0.0073(11) Uani 1 1 d .
C11 C 0.2790(6) 0.1649(8) 0.2595(4) 0.0073(11) Uani 1 1 d D
C12 C 0.3850(7) 0.1050(8) 0.2982(4) 0.0073(11) Uani 1 1 d D
H12 H 0.4571 0.1267 0.2958 0.009 Uiso 1 1 calc R
C13 C 0.3225(6) -0.0002(8) 0.3401(4) 0.0073(11) Uani 1 1 d D
H12 H 0.3589 -0.0596 0.3688 0.009 Uiso 1 1 calc R
C14 C 0.2138(6) -0.0069(8) 0.3354(4) 0.0073(11) Uani 1 1 d D
H14 H 0.1744 -0.0693 0.3604 0.009 Uiso 1 1 calc R
C9 C 0.1936(8) 0.3387(9) 0.1784(5) 0.015(2) Uani 1 1 d .
C10 C 0.2013(7) 0.4455(9) 0.1275(5) 0.015(2) Uani 1 1 d .
N1 N 0.1025(6) 0.4902(8) 0.1142(4) 0.021(2) Uani 1 1 d .
N2 N 0.0906(6) 0.3221(8) 0.1963(4) 0.020(2) Uani 1 1 d .
O1 O 0.0363(5) 0.4165(7) 0.1561(4) 0.0240(18) Uani 1 1 d .
S1 S 0.4358(2) 0.6606(3) 0.02943(14) 0.0307(11) Uani 1 1 d .
S2 S 0.1569(3) 0.1013(4) 0.28314(19) 0.0496(13) Uani 1 1 d 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'
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
C2 C1 S1 113.5(8)
C1 C2 C3 117.6(9)
C2 C3 C4 103.9(9)
C5 C4 C3 127.1(9)
C5 C4 S1 119.9(8)
C3 C4 S1 113.0(7)
C6 C5 C10 114.9(9)
C6 C5 C4 124.0(9)
C10 C5 C4 121.1(9)
C5 C6 C7 124.1(9)
C8 C7 C6 123.1(9)
C7 C8 C9 114.6(8)
C7 C8 C11 121.9(8)
C9 C8 C11 123.5(8)
C8 C11 C12 122.6(7)
C8 C11 S2 119.5(6)
C12 C11 S2 117.9(6)
C13 C12 C11 94.3(6)
C14 C13 C12 120.4(7)
C13 C14 S2 116.2(6)
N2 C9 C8 128.3(9)
N2 C9 C10 109.0(8)
C8 C9 C10 122.6(8)
N1 C10 C5 131.1(9)
N1 C10 C9 108.3(8)
C5 C10 C9 120.6(8)
C10 N1 O1 105.5(7)
C9 N2 O1 104.1(7)
N1 O1 N2 113.1(7)
C1 S1 C4 92.0(5)
C14 S2 C11 91.1(4)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.340(15)
C1 S1 1.679(10)
C2 C3 1.456(13)
C3 C4 1.498(15)
C4 C5 1.464(13)
C4 S1 1.730(11)
C5 C6 1.358(14)
C5 C10 1.440(14)
C6 C7 1.437(14)
C7 C8 1.371(13)
C8 C9 1.422(13)
C8 C11 1.493(12)
C11 C12 1.635(10)
C11 S2 1.718(8)
C12 C13 1.541(10)
C13 C14 1.366(10)
C14 S2 1.639(8)
C9 N2 1.345(13)
C9 C10 1.450(14)
C10 N1 1.340(13)
N1 O1 1.370(11)
N2 O1 1.397(10)
