Reactions between arylhydrazinium chlorides and 2-chloroquinoline-3-carbaldehydes: molecular and supramolecular structures of a hydrazone, a 4,9-dihydro-1<i>H</i>-pyrazolo[3,4-<i>b</i>]quinoline and two 1<i>H</i>-pyrazolo[3,4-<i>b</i>]quinolines
Kumara, Tholappanavara H. Suresha; Nagendrappa, Gopalpur; Chandrika, Nanjappa; Sowmya, Haliwana B. V.; Kaur, Manpreet; Jasinski, Jerry P.; Glidewell, Christopher; Acta Crystallographica Section C 72 (2016) –; doi:10.1107/S205322961601278X

data_2020569
_publ_section_title
;
 Reactions between arylhydrazinium chlorides and
 2-chloroquinoline-3-carbaldehydes: molecular and supramolecular
 structures of a hydrazone, a
 4,9-dihydro-1<i>H</i>-pyrazolo[3,4-<i>b</i>]quinoline and two
 1<i>H</i>-pyrazolo[3,4-<i>b</i>]quinolines
;
_journal_coeditor_code           SK3635
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first
;
;
_journal_paper_doi               10.1107/S205322961601278X
_journal_volume                  72
_journal_year                    2016
_chemical_formula_iupac          'C17 H13 N3'
_chemical_formula_moiety         'C17 H13 N3'
_chemical_formula_sum            'C17 H13 N3'
_chemical_formula_weight         259.30
_chemical_name_systematic
;
6-Methyl-1-phenyl-1<i>H</i>-pyrazolo[3,4-<i>b</i>]quinoline
;
_space_group_crystal_system      trigonal
_space_group_IT_number           148
_space_group_name_Hall           '-R 3'
_space_group_name_H-M_alt        'R -3 :H'
_symmetry_space_group_name_Hall  '-R 3'
_symmetry_space_group_name_H-M   'R -3 :H'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            18
_cell_length_a                   29.9202(12)
_cell_length_b                   29.9202(12)
_cell_length_c                   7.3811(3)
_cell_measurement_reflns_used    3437
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      30.275
_cell_measurement_theta_min      2.358
_cell_volume                     5722.4(4)
_computing_cell_refinement
;
CrysAlis PRO (Agilent, 2014)
;
_computing_data_collection
;
CrysAlis PRO (Agilent, 2014)
;
_computing_data_reduction
;
CrysAlis PRO (Agilent, 2014)
;
_computing_molecular_graphics
;
PLATON (Spek, 2009)
;
_computing_publication_material
;
SHELXL2014 (Sheldrick, 2015) and PLATON (Spek, 2009)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean 16.0416
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Agilent Xcalibur Eos Gemini'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0971
_diffrn_reflns_limit_h_max       36
_diffrn_reflns_limit_h_min       -38
_diffrn_reflns_limit_k_max       38
_diffrn_reflns_limit_k_min       -38
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            17651
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.546
_diffrn_reflns_theta_min         2.723
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  0.988
_exptl_absorpt_correction_T_min  0.978
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis PRO; Agilent, 2014)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.354
_exptl_crystal_description       block
_exptl_crystal_F_000             2448
_exptl_crystal_size_max          0.420
_exptl_crystal_size_mid          0.260
_exptl_crystal_size_min          0.140
_refine_diff_density_max         0.216
_refine_diff_density_min         -0.204
_refine_ls_extinction_coef       0.0006(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method
;
SHELXL2014 (Sheldrick, 2015)
;
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         2942
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0814
_refine_ls_R_factor_gt           0.0564
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0742P)^2^+4.6125P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1468
_refine_ls_wR_factor_ref         0.1729
_reflns_number_gt                2077
_reflns_number_total             2942
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            sk3635sup1.cif
_cod_data_source_block           IV
_cod_original_cell_volume        5722.4(5)
_cod_database_code               2020569
_cod_database_fobs_code          2020569
_shelx_estimated_absorpt_t_min   0.966
_shelx_estimated_absorpt_t_max   0.989
_shelx_hkl_checksum              9365
_shelx_res_checksum              59560
_shelxl_version_number           2.014