#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/20/1502075.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_1502075
loop_
_publ_author_name
'Hergué, Noémie'
'Mallet, Charlotte'
'Savitha, Gurunathan'
'Allain, Magali'
'Frère, Pierre'
'Roncali, Jean'
_publ_section_title
;
 Facile synthesis of 3-alkoxy-4-cyanothiophenes as new building blocks for
 donor-acceptor conjugated systems.
;
_journal_issue                   7
_journal_name_full               'Organic letters'
_journal_page_first              1762
_journal_page_last               1765
_journal_paper_doi               10.1021/ol200296j
_journal_volume                  13
_journal_year                    2011
_chemical_formula_moiety         'C12 H8 N2 O2 S2'
_chemical_formula_sum            'C12 H8 N2 O2 S2'
_chemical_formula_weight         276.32
_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'
_audit_creation_date             2006-06-29T15:36:52-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 112.260(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.5727(8)
_cell_length_b                   22.554(2)
_cell_length_c                   7.8420(8)
_cell_measurement_reflns_used    5540
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.4
_cell_measurement_theta_min      1.8
_cell_volume                     1239.6(2)
_computing_cell_refinement       'SELECT,CELL, STOE IPDS'
_computing_data_collection       'EXPOSE, STOE IPDS'
_computing_data_reduction        'INTEGRATE, STOE IPDS'
_computing_molecular_graphics    'DIAMOND 3.1 (Crystal Impact GbR 2005)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'Direct methods (Sir92,Altomare et al.,1993)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 6.66
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'STOE IPDS'
_diffrn_measurement_method       'Oscillation Phi Incr 1.0 deg'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.087
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            9369
_diffrn_reflns_theta_full        25.93
_diffrn_reflns_theta_max         25.93
_diffrn_reflns_theta_min         2.91
_exptl_absorpt_coefficient_mu    0.423
_exptl_absorpt_correction_T_max  0.9982
_exptl_absorpt_correction_T_min  0.9197
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
 PLATON-ABSGAUSS : Spek, A.L. (2003), J.Appl.Cryst. 36, 7-13
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.481
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.54
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.26
_refine_diff_density_min         -0.262
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.851
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         2375
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.851
_refine_ls_R_factor_gt           0.0402
_refine_ls_shift/su_max          0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0534P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1117
_reflns_number_gt                1172
_reflns_number_total             2375
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol200296j_si_002.cif
_cod_data_source_block           nh2581y
_cod_database_code               1502075
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_calc_flag
_atom_site_refinement_flags
C01 C 0.2824(5) 0.58927(14) 0.1774(4) 0.0516(9) Uani 1 d .
H01 H 0.2771 0.605 0.0659 0.062 Uiso 1 calc R
C02 C 0.3414(5) 0.61980(12) 0.3376(4) 0.0433(8) Uani 1 d .
C03 C 0.3318(5) 0.58505(12) 0.4862(4) 0.0408(7) Uani 1 d .
C04 C 0.2689(4) 0.52816(12) 0.4362(4) 0.0404(7) Uani 1 d .
C05 C 0.2402(4) 0.48092(12) 0.5486(4) 0.0397(7) Uani 1 d .
C06 C 0.1788(5) 0.42425(13) 0.4956(4) 0.0480(8) Uani 1 d .
C07 C 0.1661(5) 0.38875(14) 0.6421(4) 0.0522(9) Uani 1 d .
C08 C 0.2214(5) 0.42021(15) 0.8020(5) 0.0588(10) Uani 1 d .
H08 H 0.2239 0.4044 0.9125 0.071 Uiso 1 calc R
C09 C 0.3866(7) 0.71222(16) 0.2165(5) 0.0773(12) Uani 1 d .
H09A H 0.4554 0.6946 0.1488 0.116 Uiso 1 calc R
H09B H 0.4368 0.7511 0.2572 0.116 Uiso 1 calc R
H09C H 0.254 0.7153 0.1387 0.116 Uiso 1 calc R
C10 C 0.3833(5) 0.60976(13) 0.6666(4) 0.0527(8) Uani 1 d .
C11 C 0.1135(6) 0.34831(15) 0.2635(5) 0.0740(12) Uani 1 d .
H11A H 0.2211 0.3263 0.3447 0.111 Uiso 1 calc R
H11B H 0.1077 0.3449 0.1395 0.111 Uiso 1 calc R
H11C H -0.0015 0.3327 0.2704 0.111 Uiso 1 calc R
C12 C 0.1008(6) 0.32899(16) 0.6331(5) 0.0680(11) Uani 1 d .
N01 N 0.4240(5) 0.63077(13) 0.8079(4) 0.0784(10) Uani 1 d .
N02 N 0.0489(6) 0.28201(15) 0.6355(5) 0.1023(13) Uani 1 d .
O01 O 0.4072(4) 0.67599(9) 0.3736(3) 0.0594(7) Uani 1 d .
O02 O 0.1332(4) 0.40858(10) 0.3165(3) 0.0754(8) Uani 1 d .
S01 S 0.21873(14) 0.51831(3) 0.20470(10) 0.0504(3) Uani 1 d .
S02 S 0.28445(14) 0.49015(4) 0.78048(11) 0.0540(3) Uani 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 0 '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 0.006 '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
C02 C01 S01 111.7(2)
O01 C02 C01 129.6(3)
O01 C02 C03 118.2(2)
C01 C02 C03 112.2(3)
C04 C03 C02 113.5(2)
C04 C03 C10 125.6(3)
C02 C03 C10 120.9(3)
C03 C04 C05 128.9(2)
C03 C04 S01 109.6(2)
C05 C04 S01 121.5(2)
C06 C05 C04 127.8(3)
C06 C05 S02 109.8(2)
C04 C05 S02 122.4(2)
O02 C06 C05 118.7(3)
O02 C06 C07 127.9(3)
C05 C06 C07 113.3(3)
C08 C07 C12 121.1(3)
C08 C07 C06 110.9(3)
C12 C07 C06 127.9(3)
C07 C08 S02 113.4(2)
N01 C10 C03 178.3(3)
N02 C12 C07 176.2(4)
C02 O01 C09 116.3(2)
C06 O02 C11 120.7(3)
C01 S01 C04 92.94(13)
C08 S02 C05 92.50(15)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C01 C02 1.352(4)
C01 S01 1.708(3)
C02 O01 1.352(3)
C02 C03 1.429(4)
C03 C04 1.373(4)
C03 C10 1.430(4)
C04 C05 1.451(4)
C04 S01 1.722(3)
C05 C06 1.370(4)
C05 S02 1.732(3)
C06 O02 1.360(4)
C06 C07 1.433(4)
C07 C08 1.362(5)
C07 C12 1.428(5)
C08 S02 1.675(3)
C09 O01 1.437(4)
C10 N01 1.136(4)
C11 O02 1.413(4)
C12 N02 1.133(4)
