Crystal structure of 5-(5-chloro-2-hydroxybenzoyl)-2-(2-methyl-1<i>H</i>-indol-3-yl)nicotinonitrile
Vimala, G.; Poomathi, N.; AaminaNaaz, Y.; Perumal, P. T.; SubbiahPandi, A.; Acta Crystallographica Section E 71 (2015) o822–o823; doi:10.1107/S2056989015018058

data_2241186
_publ_section_title
;
 Crystal structure of
 5-(5-chloro-2-hydroxybenzoyl)-2-(2-methyl-1<i>H</i>-indol-3-yl)nicotinonitrile
;
_journal_coeditor_code           ZP2018
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o822
_journal_page_last               o823
_journal_paper_doi               10.1107/S2056989015018058
_journal_volume                  71
_journal_year                    2015
_chemical_formula_iupac          'C22 H14 Cl N3 O2'
_chemical_formula_moiety         'C22 H14 Cl N3 O2'
_chemical_formula_sum            'C22 H14 Cl N3 O2'
_chemical_formula_weight         387.81
_chemical_name_common
;
5-(5-Chloro-2-hydroxybenzoyl)-2-(2-methyl-1<i>H</i>-indol-3-yl)nicotinonitrile
;
_chemical_name_systematic
5-(5-Chloro-2-hydroxybenzoyl)-2-(2-methyl-1<i>H</i>-indol-3-yl)pyridine-3-carbonitrile
_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                 113.452(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   16.0673(15)
_cell_length_b                   7.4804(7)
_cell_length_c                   17.0159(15)
_cell_measurement_reflns_used    2447
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.89
_cell_measurement_theta_min      1.48
_cell_volume                     1876.2(3)
_computing_cell_refinement
;
APEX2 and SAINT (Bruker, 2008)
;
_computing_data_collection
;
APEX2 (Bruker, 2008)
;
_computing_data_reduction
;
SAINT and XPREP (Bruker, 2008)
;
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012)
;
_computing_publication_material
;
PLATON (Spek, 2009)
;
_computing_structure_refinement
;
SHELXL97 (Sheldrick, 2008)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 0
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device_type  'Bruker Kappa APEXII CCD'
_diffrn_measurement_method       '\w and \f scan'
_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  0.0383
_diffrn_reflns_av_sigmaI/netI    0.0562
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            7690
_diffrn_reflns_theta_full        25.89
_diffrn_reflns_theta_max         25.89
_diffrn_reflns_theta_min         1.48
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.227
_exptl_absorpt_correction_T_max  0.960
_exptl_absorpt_correction_T_min  0.941
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2008)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.373
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.429
_refine_diff_density_min         -0.361
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         3638
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.013
_refine_ls_R_factor_all          0.0850
_refine_ls_R_factor_gt           0.0570
_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^)+(0.0793P)^2^+1.1008P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1477
_refine_ls_wR_factor_ref         0.1701
_reflns_number_gt                2447
_reflns_number_total             3638
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            zp2018sup1.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2241186
_cod_database_fobs_code          2241186