A structural systematic study of four isomers of difluoro-<i>N</i>-(3-pyridyl)benzamide
McMahon, Joyce; Gallagher, John F.; Anderson, Frankie P.; Lough, Alan J.; Acta Crystallographica Section C 65 (2009) o345–o351; doi:10.1107/S010827010902215X

data_2017204
_publ_section_title
;
 A structural systematic study of four isomers of
 difluoro-<i>N</i>-(3-pyridyl)benzamide
;
_journal_coeditor_code           SK3328
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o345
_journal_page_last               o351
_journal_paper_doi               10.1107/S010827010902215X
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C12 H8 F2 N2 O'
_chemical_formula_moiety         'C12 H8 F2 N2 O'
_chemical_formula_structural     'C12 H8 F2 N2 O'
_chemical_formula_sum            'C12 H8 F2 N2 O'
_chemical_formula_weight         234.20
_chemical_melting_point          437
_chemical_name_common            35m
_chemical_name_systematic
;
3,5-difluoro-<i>N</i>-(3-pyridyl)benzamide
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 101.152(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.3784(5)
_cell_length_b                   12.6278(8)
_cell_length_c                   9.9118(5)
_cell_measurement_reflns_used    3690
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      2.55
_cell_volume                     1028.87(10)
_computing_cell_refinement       'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_data_collection       'KappaCCD Server Software (Nonius, 1997)'
_computing_data_reduction        'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material
;
SHELXL97 (Sheldrick, 2008) and PREP8 (Ferguson, 1998)
;
_computing_structure_refinement
;
SHELXL97 (Sheldrick, 2008) and SORTX (McArdle, 1995)
;
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      150.0(10)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device       'Nonius KappaCCD'
_diffrn_measurement_method       '\f, \w scans with \k offsets'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed X-ray tube'
_diffrn_radiation_type           'Molybdenum K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0455
_diffrn_reflns_av_sigmaI/netI    0.0560
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            7054
_diffrn_reflns_theta_full        27.47
_diffrn_reflns_theta_max         27.47
_diffrn_reflns_theta_min         2.64
_diffrn_standards_number         2916
_exptl_absorpt_coefficient_mu    0.124
_exptl_absorpt_correction_T_max  0.983
_exptl_absorpt_correction_T_min  0.938
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SORTAV; Blessing, 1995)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.512
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             480
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.266
_refine_diff_density_min         -0.238
_refine_ls_extinction_coef       0.014(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     159
_refine_ls_number_reflns         2348
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0921
_refine_ls_R_factor_gt           0.0514
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.0788P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1203
_refine_ls_wR_factor_ref         0.1409
_reflns_number_gt                1535
_reflns_number_total             2348
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            sk3328.cif
_cod_data_source_block           IV
_cod_original_sg_symbol_Hall     '-p 2yn'
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2017204
_cod_database_fobs_code          2017204