Hydrogen-bonded structures of the isomeric compounds of phthalazine with 3-chloro-2-nitrobenzoic acid, 4-chloro-2-nitrobenzoic acid and 4-chloro-3-nitrobenzoic acid
Gotoh, Kazuma; Ishida, Hiroyuki; Acta Crystallographica Section C 67 (2011) o473–o478; doi:10.1107/S0108270111044829

data_2018280
_publ_section_title
;
 Hydrogen-bonded structures of the isomeric compounds of phthalazine with
 3-chloro-2-nitrobenzoic acid, 4-chloro-2-nitrobenzoic acid and
 4-chloro-3-nitrobenzoic acid
;
_journal_coeditor_code           FG3232
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o473
_journal_page_last               o478
_journal_paper_doi               10.1107/S0108270111044829
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C7 H3.69 Cl N O4 , C8 H6.31 N2'
_chemical_formula_moiety         'C7 H3.69 Cl N O4, C8 H6.31 N2'
_chemical_formula_sum            'C15 H10 Cl N3 O4'
_chemical_formula_weight         331.71
_chemical_name_systematic
;
4-chloro-2-nitrobenzoic acid--phthalazine (1/1)
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.0000
_cell_angle_beta                 106.8955(13)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            8
_cell_length_a                   12.2261(5)
_cell_length_b                   16.9779(7)
_cell_length_c                   14.4537(6)
_cell_measurement_reflns_used    42486
_cell_measurement_temperature    190.0(10)
_cell_measurement_theta_max      29.9
_cell_measurement_theta_min      3.1
_cell_volume                     2870.7(2)
_computing_cell_refinement       'PROCESS-AUTO (Rigaku/MSC, 2004)'
_computing_data_collection       'PROCESS-AUTO (Rigaku/MSC, 2004)'
_computing_data_reduction        'CrystalStructure (Rigaku/MSC, 2004)'
_computing_molecular_graphics
;
ORTEP-3 (Farrugia, 1997) and WinGX (Farrugia, 1999)
;
_computing_publication_material
;
CrystalStructure (Rigaku/MSC, 2004) and PLATON (Spek, 2009)
;
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      190.0(10)
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID II'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.030
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            60079
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         29.96
_exptl_absorpt_coefficient_mu    0.291
_exptl_absorpt_correction_T_max  0.916
_exptl_absorpt_correction_T_min  0.790
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(ABSCOR; Higashi, 1995)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.535
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1360.00
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.713
_refine_diff_density_min         -0.407
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     429
_refine_ls_number_reflns         8318
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.0507
_refine_ls_R_factor_gt           0.0416
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[\s^2^(Fo^2^)+(0.0667P)^2^+0.6974P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1170
_refine_ls_wR_factor_ref         0.1226
_reflns_number_gt                6797
_reflns_number_total             8318
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            fg3232.cif
_cod_data_source_block           II
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2018280
_cod_database_fobs_code          2018280