4-(2-Fluorophenyl)-6-(1<i>H</i>-indol-1-yl)-3-methyl-1-phenyl-1<i>H</i>-pyrazolo[3,4-<i>b</i>]pyridine-5-carbonitrile: a chain of rings built from N—H···N, C—H···N and C—H···π(arene) hydrogen bonds
Quiroga, Jairo; Sánchez, Ana; Cobo, Justo; Glidewell, Christopher; Acta Crystallographica Section C 65 (2009) o374–o376; doi:10.1107/S0108270109025566

data_2017269
_publ_section_title
;4-(2-Fluorophenyl)-6-(1<i>H</i>-indol-1-yl)-3-methyl-1-phenyl-1<i>H</i>-pyrazolo[3,4-<i>b</i>]pyridine-5-carbonitrile:
 a chain of rings built from N---H&#x00B7;&#x00B7;&#x00B7;N,
 C---H&#x00B7;&#x00B7;&#x00B7;N and C---H&#x00B7;&#x00B7;&#x00B7;\p(arene)
 hydrogen bonds
;
_journal_coeditor_code           SU3034
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o374
_journal_page_last               o376
_journal_paper_doi               10.1107/S0108270109025566
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C28 H18 F N5'
_chemical_formula_moiety         'C28 H18 F N5'
_chemical_formula_sum            'C28 H18 F N5'
_chemical_formula_weight         443.47
_chemical_name_systematic
;
4-(2-Fluorophenyl)-6-(1<i>H</i>-indol-1-yl)-3-methyl-1-phenyl-1<i>H</i>-
pyrazolo[3,4-<i>b</i>]pyridine-5-carbonitrile
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 105.743(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   24.155(3)
_cell_length_b                   10.5830(7)
_cell_length_c                   18.712(3)
_cell_measurement_reflns_used    5280
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.50
_cell_measurement_theta_min      3.21
_cell_volume                     4604.0(10)
_computing_cell_refinement       'DIRAX/LSQ (Duisenberg <i>et al.</i>,  2000)'
_computing_data_collection       'COLLECT (Hooft, 1999)'
_computing_data_reduction        'EVALCCD (Duisenberg <i>et al.</i>,  2003)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material
'SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 9.091
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker Nonius KappaCCD'
_diffrn_measurement_method       '\f & \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Bruker-Nonius FR591 rotating anode'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0647
_diffrn_reflns_av_sigmaI/netI    0.0466
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            51259
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         3.21
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  0.979
_exptl_absorpt_correction_T_min  0.968
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2003)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.280
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1840
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.375
_refine_diff_density_min         -0.287
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     308
_refine_ls_number_reflns         5280
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.095
_refine_ls_R_factor_all          0.1130
_refine_ls_R_factor_gt           0.0687
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1279P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1803
_refine_ls_wR_factor_ref         0.2109
_reflns_number_gt                3346
_reflns_number_total             5280
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            su3034.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2017269
_cod_database_fobs_code          2017269