Facile synthesis of 3-alkoxy-4-cyanothiophenes as new building blocks for donor-acceptor conjugated systems.
Hergué, Noémie; Mallet, Charlotte; Savitha, Gurunathan; Allain, Magali; Frère, Pierre; Roncali, Jean; Organic letters 13 (2011) 1762–1765; doi:10.1021/ol200296j

data_1502075
_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/[\s^2^(Fo^2^)+(0.0534P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/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