3,5-Dichloro-4-cyanobenzoic acid: two polymorphs and the 0.25-hydrate, exhibiting two-dimensional ribbons and nets involving hydrogen-bonding and intermolecular Cl···N interactions
Britton, Doyle; Acta Crystallographica Section C 62 (2006) o510–o514; doi:10.1107/S0108270106023754

data_2015510
_publ_section_title
;
 3,5-Dichloro-4-cyanobenzoic acid: two polymorphs and the 0.25-hydrate,
 exhibiting two-dimensional ribbons and nets involving hydrogen-bonding
 and intermolecular Cl&#x00B7;&#x00B7;&#x00B7;N interactions
;
_journal_coeditor_code           LN3011
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o510
_journal_page_last               o514
_journal_paper_doi               10.1107/S0108270106023754
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C8 H3 Cl2 N O2 , 0.25H2 O'
_chemical_formula_moiety         'C8 H3 Cl2 N O2 , 0.25H2 O'
_chemical_formula_sum            'C8 H3.5 Cl2 N O2.25'
_chemical_formula_weight         220.52
_chemical_name_systematic
;
 3,5-dichloro-4-cyanobenzoicacid  0.25-hydrate
;
_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           SHELXTL
_cell_angle_alpha                90.00
_cell_angle_beta                 112.500(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   11.237(3)
_cell_length_b                   11.410(3)
_cell_length_c                   14.566(4)
_cell_measurement_reflns_used    2775
_cell_measurement_temperature    174(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      2.2
_cell_volume                     1725.4(8)
_computing_cell_refinement       'SAINT (Bruker, 2003)'
_computing_data_collection       'SMART (Bruker, 2003)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL (Sheldrick, 1997)'
_diffrn_ambient_temperature      174(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Bruker SMART 1K CCD area-detector'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.024
_diffrn_reflns_av_sigmaI/netI    0.018
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            19254
_diffrn_reflns_theta_full        26.4
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         1.97
_diffrn_standards_decay_%        <1
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.715
_exptl_absorpt_correction_T_max  0.84
_exptl_absorpt_correction_T_min  0.76
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Sheldrick, 2003; Blessing, 1995)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.698
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             884
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.411
_refine_diff_density_min         -0.457
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.04
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     251
_refine_ls_number_reflns         3893
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.04
_refine_ls_R_factor_all          0.036
_refine_ls_R_factor_gt           0.027
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.035P)^2^+0.92P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.069
_refine_ls_wR_factor_ref         0.076
_reflns_number_gt                3265
_reflns_number_total             3893
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            ln3011.cif
_cod_data_source_block           III
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_original_formula_sum        'C8 H3.50 Cl2 N O2.25'
_cod_database_code               2015510
_cod_database_fobs_code          2015510