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_2018530
_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_melting_point          432
_chemical_name_common            2-(4-fluorophenyl)-perhydroisoindolyl-1,3-dione
_chemical_name_systematic
;
<i>cis</i>-2-(4-fluorophenyl)-3a,4,5,6,7,7a-hexahydroisoindoline-1,3-dione
;
_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                 95.275(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.7554(3)
_cell_length_b                   6.6709(2)
_cell_length_c                   16.8466(4)
_cell_measurement_reflns_used    3937
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      28.80
_cell_measurement_theta_min      3.28
_cell_volume                     1203.59(6)
_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_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0231
_diffrn_reflns_av_sigmaI/netI    0.0292
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            7621
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         3.29
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_T_max  0.990
_exptl_absorpt_correction_T_min  0.960
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrysAlis PRO; Oxford Diffraction, 2010)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.365
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.35
_refine_diff_density_max         0.195
_refine_diff_density_min         -0.208
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2362
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0489
_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^)+(0.0535P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0871
_refine_ls_wR_factor_ref         0.0905
_reflns_number_gt                1826
_reflns_number_total             2362
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            fg3250.cif
_cod_data_source_block           III
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2018530
_cod_database_fobs_code          2018530