Hydrogen-bonded assembly in six closely related pyrazolo[3,4-<i>b</i>]pyridine derivatives; a simple chain, three types of chains of rings and a complex sheet structure
Quiroga, Jairo; Díaz, Yurina; Cobo, Justo; Glidewell, Christopher; Acta Crystallographica Section C 68 (2012) o12–o18; doi:10.1107/S0108270111050207

data_2018360
_publ_section_title
;
 Hydrogen-bonded assembly in six closely related
 pyrazolo[3,4-<i>b</i>]pyridine derivatives; a simple chain, three types
 of chains of rings and a complex sheet structure
;
_journal_coeditor_code           YF3009
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o12
_journal_page_last               o18
_journal_paper_doi               10.1107/S0108270111050207
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C21 H16 Cl N3 O'
_chemical_formula_moiety         'C21 H16 Cl N3 O'
_chemical_formula_sum            'C21 H16 Cl N3 O'
_chemical_formula_weight         361.82
_chemical_name_systematic
;
6-Chloro-3-methyl-4-(4-methylphenyl)-1-phenyl-
pyrazolo[3,4-<i>b</i>]pyridine-5-carbaldehyde
;
_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                87.108(11)
_cell_angle_beta                 86.808(8)
_cell_angle_gamma                85.088(12)
_cell_formula_units_Z            2
_cell_length_a                   8.2898(8)
_cell_length_b                   9.9191(14)
_cell_length_c                   10.3666(10)
_cell_measurement_reflns_used    3880
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.49
_cell_measurement_theta_min      2.79
_cell_volume                     847.08(17)
_computing_cell_refinement       'DIRAX/LSQ (Duisenberg <i>et al.</i>, 2000)'
_computing_data_collection       'COLLECT (Nonius, 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 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker Nonius KappaCCD area-detector'
_diffrn_measurement_method       '\f and \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  0.0735
_diffrn_reflns_av_sigmaI/netI    0.0661
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            21387
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         2.79
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.241
_exptl_absorpt_correction_T_max  0.953
_exptl_absorpt_correction_T_min  0.929
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2003)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.419
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             376
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.310
_refine_diff_density_min         -0.301
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         3880
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0977
_refine_ls_R_factor_gt           0.0502
_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^)+(0.0595P)^2^+0.3061P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1077
_refine_ls_wR_factor_ref         0.1297
_reflns_number_gt                2544
_reflns_number_total             3880
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            yf3009.cif
_cod_data_source_block           II
_cod_database_code               2018360
_cod_database_fobs_code          2018360