Hydrogen bonding in cyclic imides and amide carboxylic acid derivatives from the facile reaction of <i>cis</i>-cyclohexane-1,2-carboxylic anhydride with <i>o</i>- and <i>p</i>-anisidine and <i>m</i>- and <i>p</i>-aminobenzoic acids
Smith, Graham; Wermuth, Urs D.; Acta Crystallographica Section C 68 (2012) o327–o331; doi:10.1107/S0108270112030168

data_2018596
_publ_section_title
;
 Hydrogen bonding in cyclic imides and amide carboxylic acid derivatives
 from the facile reaction of <i>cis</i>-cyclohexane-1,2-carboxylic
 anhydride with <i>o</i>- and <i>p</i>-anisidine and <i>m</i>- and
 <i>p</i>-aminobenzoic acids
;
_journal_coeditor_code           BM3120
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o327
_journal_page_last               o331
_journal_paper_doi               10.1107/S0108270112030168
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C15 H15 N O4, H2 O'
_chemical_formula_moiety         'C15 H15 N O4, H2 O'
_chemical_formula_sum            'C15 H17 N O5'
_chemical_formula_weight         291.30
_chemical_name_systematic
;
<i>rac</i>-<i>cis</i>-4-(1,3-dioxo-3a,4,5,6,7,7a-hexahydroisoindol-
2-yl)benzoic acid monohydrate
;
_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           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 97.982(13)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.077(2)
_cell_length_b                   6.6713(7)
_cell_length_c                   16.432(2)
_cell_measurement_reflns_used    2417
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      28.74
_cell_measurement_theta_min      3.13
_cell_volume                     1419.6(3)
_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>, 1993)'
_diffrn_ambient_temperature      200(2)
_diffrn_detector_area_resol_mean 16.077
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type
'Oxford Diffraction Gemini-S CCD-detector diffractometer'
_diffrn_measurement_method       '\w scans'
_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  0.0546
_diffrn_reflns_av_sigmaI/netI    0.0810
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            9649
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         3.15
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_T_max  0.980
_exptl_absorpt_correction_T_min  0.813
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrysAlis PRO; Oxford Diffraction, 2010)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.363
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.342
_refine_diff_density_min         -0.195
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.853
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     194
_refine_ls_number_reflns         2790
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.853
_refine_ls_R_factor_all          0.1064
_refine_ls_R_factor_gt           0.0518
_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^)+(0.0704P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1217
_refine_ls_wR_factor_ref         0.1322
_reflns_number_gt                1374
_reflns_number_total             2790
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            bm3120.cif
_cod_data_source_block           IV
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2018596
_cod_database_fobs_code          2018596