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_2018281
_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 H4 Cl N O4 , C8 H6 N2'
_chemical_formula_moiety         'C7 H4 Cl N O4, C8 H6 N2'
_chemical_formula_sum            'C15 H10 Cl N3 O4'
_chemical_formula_weight         331.71
_chemical_name_systematic
;
4-chloro-3-nitrobenzoic acid--phthalazine (1/1)
;
_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
_cell_angle_alpha                81.704(2)
_cell_angle_beta                 79.0781(18)
_cell_angle_gamma                85.647(2)
_cell_formula_units_Z            4
_cell_length_a                   6.9197(5)
_cell_length_b                   14.4263(12)
_cell_length_c                   14.4750(9)
_cell_measurement_reflns_used    15895
_cell_measurement_temperature    190.0(10)
_cell_measurement_theta_max      30.1
_cell_measurement_theta_min      3.0
_cell_volume                     1402.20(18)
_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 0.985
_diffrn_measured_fraction_theta_max 0.956
_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  0.0558
_diffrn_reflns_av_sigmaI/netI    0.0643
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            22476
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         30.03
_exptl_absorpt_coefficient_mu    0.298
_exptl_absorpt_correction_T_max  0.982
_exptl_absorpt_correction_T_min  0.929
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   '(NUMABS; Higashi, 1999)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.571
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             680.00
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.526
_refine_diff_density_min         -0.480
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.993
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     423
_refine_ls_number_reflns         7849
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.993
_refine_ls_R_factor_all          0.0852
_refine_ls_R_factor_gt           0.0574
_refine_ls_shift/su_max_lt       0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[\s^2^(Fo^2^)+(0.0810P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1426
_refine_ls_wR_factor_ref         0.1538
_reflns_number_gt                4765
_reflns_number_total             7849
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            fg3232.cif
_cod_data_source_block           III
_cod_original_cell_volume        1402.20(17)
_cod_database_code               2018281
_cod_database_fobs_code          2018281