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_1502076
_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         'C26 H36 N2 O2 S2'
_chemical_formula_sum            'C26 H36 N2 O2 S2'
_chemical_formula_weight         472.69
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_audit_creation_date             2009-09-21T18:14:34-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                77.02(3)
_cell_angle_beta                 83.19(3)
_cell_angle_gamma                82.81(3)
_cell_formula_units_Z            2
_cell_length_a                   5.046(2)
_cell_length_b                   14.874(5)
_cell_length_c                   18.545(7)
_cell_measurement_reflns_used    2378
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26
_cell_measurement_theta_min      2.4
_cell_volume                     1339.7(9)
_computing_cell_refinement       'Dirax/lsq (Duisenberg & Schreurs, 1989-2000)'
_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_data_reduction        'EvalCCD (Duisenberg & Schreurs 1990-2000)'
_computing_molecular_graphics    'DIAMOND 3.2c (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 9
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       CCD
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1188
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            19910
_diffrn_reflns_theta_full        26
_diffrn_reflns_theta_max         26
_diffrn_reflns_theta_min         2.4
_exptl_absorpt_coefficient_mu    0.222
_exptl_absorpt_correction_T_max  0.996
_exptl_absorpt_correction_T_min  0.756
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 '(SADABS (Sheldrick, Bruker, 2000))'
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.172
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             508
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.741
_refine_diff_density_min         -0.302
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     293
_refine_ls_number_reflns         5226
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_gt           0.0911
_refine_ls_shift/su_max          0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0875P)^2^+1.6335P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.246
_reflns_number_gt                2485
_reflns_number_total             5226
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol200296j_si_003.cif
_cod_data_source_block           nanny
_cod_database_code               1502076