A hydrogen-bonded dimer in 6-(4-bromophenyl)-3-methyl-1-phenyl-4,5-dihydro-1<i>H</i>-pyrazolo[3,4-<i>b</i>]pyridine and a chain of rings built from N—H···N and C—H···π(pyridine) hydrogen bonds in 3-(4-nitrophenyl)-4-phenyl-1<i>H</i>-pyrazolo[3,4-<i>b</i>]pyridine
Quiroga, Jairo; Trilleras, Jorge; Hursthouse, Michael B.; Cobo, Justo; Glidewell, Christopher; Acta Crystallographica Section C 66 (2010) o163–o167; doi:10.1107/S0108270110006451

data_2017594
_publ_section_title
;
 A hydrogen-bonded dimer in
 6-(4-bromophenyl)-3-methyl-1-phenyl-4,5-dihydro-1<i>H</i>-pyrazolo[3,4-<i>b</i>]pyridine
 and a chain of rings built from N---H&#x00B7;&#x00B7;&#x00B7;N and
 C---H&#x00B7;&#x00B7;&#x00B7;\p(pyridine) hydrogen bonds in
 3-(4-nitrophenyl)-4-phenyl-1<i>H</i>-pyrazolo[3,4-<i>b</i>]pyridine
;
_journal_coeditor_code           EG3040
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o163
_journal_page_last               o167
_journal_paper_doi               10.1107/S0108270110006451
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C19 H16 Br N3'
_chemical_formula_moiety         'C19 H16 Br N3'
_chemical_formula_sum            'C19 H16 Br N3'
_chemical_formula_weight         366.26
_chemical_name_systematic
;
6-(4-bromophenyl)-3-methyl-1-phenyl-4,5-dihydro-1<i>H</i>-
pyrazolo[3,4-<i>b</i>]pyridine
;
_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                90.00
_cell_angle_beta                 92.701(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.51650(10)
_cell_length_b                   11.6572(3)
_cell_length_c                   17.6917(5)
_cell_measurement_reflns_used    3058
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      26.05
_cell_measurement_theta_min      3.23
_cell_volume                     1548.45(6)
_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    'Sir2004 (Burla <i>et al.</i>,  2005)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 9.091
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0477
_diffrn_reflns_av_sigmaI/netI    0.0318
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_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            21038
_diffrn_reflns_theta_full        26.05
_diffrn_reflns_theta_max         26.05
_diffrn_reflns_theta_min         3.23
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.657
_exptl_absorpt_correction_T_max  0.901
_exptl_absorpt_correction_T_min  0.685
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2003)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.571
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.263
_refine_diff_density_min         -0.513
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         3058
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0385
_refine_ls_R_factor_gt           0.0292
_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^)+(0.0284P)^2^+1.0784P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0658
_refine_ls_wR_factor_ref         0.0694
_reflns_number_gt                2597
_reflns_number_total             3058
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            eg3040.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_exptl_absorpt_correction_type' value 'Multi-scan' changed to
'multi-scan' according to
'/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2017594
_cod_database_fobs_code          2017594