4-(3-Fluoroanilino)thieno[2,3-<i>b</i>]pyridine-6-carboxylic acid
Pinheiro, Luiz C. S.; Bernardino, Alice M. R.; Wardell, Solange M. S. V.; Wardell, James L.; Tiekink, Edward R. T.; Acta Crystallographica Section E 68 (2012) o2217–o2218; doi:10.1107/S1600536812027195

data_2235473
_publ_section_title
;
 4-(3-Fluoroanilino)thieno[2,3-<i>b</i>]pyridine-6-carboxylic acid
;
_journal_coeditor_code           HB6844
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2217
_journal_page_last               o2218
_journal_paper_doi               10.1107/S1600536812027195
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C14 H9 F N2 O2 S'
_chemical_formula_moiety         'C14 H9 F N2 O2 S'
_chemical_formula_sum            'C14 H9 F N2 O2 S'
_chemical_formula_weight         288.29
_chemical_name_systematic
;
4-(3-Fluoroanilino)thieno[2,3-<i>b</i>]pyridine-6-carboxylic acid
;
_space_group_IT_number           33
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_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            4
_cell_length_a                   17.0666(6)
_cell_length_b                   8.7147(3)
_cell_length_c                   7.9931(2)
_cell_measurement_reflns_used    1601
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      1.00
_cell_volume                     1188.82(7)
_computing_cell_refinement
'DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998)'
_computing_data_collection       'COLLECT (Hooft, 1998)'
_computing_data_reduction
'DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998)'
_computing_molecular_graphics
'ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006)'
_computing_publication_material  'publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 9.091
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type
'Bruker--Nonius Roper CCD camera on \k-goniostat'
_diffrn_measurement_method       '\f & \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Bruker-Nonius FR591 rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0581
_diffrn_reflns_av_sigmaI/netI    0.0529
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            10259
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         3.46
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.287
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.787846
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2007)'
_exptl_crystal_colour            dark-orange
_exptl_crystal_density_diffrn    1.611
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       blade
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.66
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.203
_refine_diff_density_min         -0.420
_refine_ls_abs_structure_details 'Flack (1983), 1181 Friedel pairs'
_refine_ls_abs_structure_Flack   0.15(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     197
_refine_ls_number_reflns         2643
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0432
_refine_ls_R_factor_gt           0.0353
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0375P)^2^+0.2847P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0841
_refine_ls_wR_factor_ref         0.0872
_reflns_number_gt                2376
_reflns_number_total             2643
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            hb6844.cif
_cod_data_source_block           I
_cod_original_sg_symbol_Hall     'P 2c -2n '
_cod_database_code               2235473
_cod_database_fobs_code          2235473