Cyclic imides and an open-chain amide carboxylic acid from the facile reaction of <i>cis</i>-cyclohexane-1,2-carboxylic anhydride with the isomeric monofluoroanilines
Smith, Graham; Wermuth, Urs D.; Acta Crystallographica Section C 68 (2012) o253–o256; doi:10.1107/S010827011202447X

data_2018528
_publ_section_title
;
 Cyclic imides and an open-chain amide carboxylic acid from the facile
 reaction of <i>cis</i>-cyclohexane-1,2-carboxylic anhydride with the
 isomeric monofluoroanilines
;
_journal_coeditor_code           FG3250
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o253
_journal_page_last               o256
_journal_paper_doi               10.1107/S010827011202447X
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C14 H14 F N O2'
_chemical_formula_moiety         'C14 H14 F N O2'
_chemical_formula_sum            'C14 H14 F N O2'
_chemical_formula_weight         247.26
_chemical_name_common            2-(2-fluorophenyl)-perhydroisoindole-1,3-dione
_chemical_name_systematic
;
<i>cis</i>-2-(2-fluorophenyl)-3a,4,5,6,7,7a-hexahydroisoindole-1,3-dione
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                98.595(4)
_cell_angle_beta                 93.324(4)
_cell_angle_gamma                97.260(4)
_cell_formula_units_Z            2
_cell_length_a                   8.0316(4)
_cell_length_b                   8.1702(4)
_cell_length_c                   9.2085(5)
_cell_measurement_reflns_used    3763
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      28.76
_cell_measurement_theta_min      3.266
_cell_volume                     590.86(5)
_computing_cell_refinement       'CrysAlis PRO (Oxford Diffraction, 2010)'
_computing_data_collection       'CrysAlis PRO (Oxford Diffraction, 2010)'
_computing_data_reduction        'CrysAlis PRO (Oxford Diffraction, 2010)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'PLATON (Spek, 2009)'
_computing_structure_refinement
;
SHELXL97 (Sheldrick, 2008) within WinGX (Farrugia, 1999)
;
_computing_structure_solution    'SIR92 (Altomare <i>et al.</i>, 1994)'
_diffrn_ambient_temperature      200(2)
_diffrn_detector_area_resol_mean 16.077
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Oxford Gemini-S CCD area-detector'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0223
_diffrn_reflns_av_sigmaI/netI    0.0277
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            7051
_diffrn_reflns_theta_full        25.99
_diffrn_reflns_theta_max         25.99
_diffrn_reflns_theta_min         3.27
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_T_max  0.989
_exptl_absorpt_correction_T_min  0.969
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrysAlis PRO; Oxford Diffraction, 2010)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.390
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             260
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.235
_refine_diff_density_min         -0.201
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2305
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.076
_refine_ls_R_factor_all          0.0494
_refine_ls_R_factor_gt           0.0354
_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^)+(0.0572P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0939
_refine_ls_wR_factor_ref         0.0979
_reflns_number_gt                1783
_reflns_number_total             2305
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            fg3250.cif
_cod_data_source_block           I
_cod_database_code               2018528
_cod_database_fobs_code          2018528