Three closely related 4,5,6,7-tetrahydro-1<i>H</i>-pyrazolo[4,3-<i>c</i>]pyridines: synthesis, molecular conformations and hydrogen bonding in zero, one and two dimensions
Sagar, Belakavadi K.; Harsha, Kachigere B.; Yathirajan, Hemmige S.; Rangappa, Kanchugarakoppal S.; Rathore, Ravindranath S.; Glidewell, Christopher; Acta Crystallographica Section C 73 (2017) 298–304; doi:10.1107/S205322961700273X

data_2020721
_publ_section_title
;
 Three closely related
 4,5,6,7-tetrahydro-1<i>H</i>-pyrazolo[4,3-<i>c</i>]pyridines: synthesis,
 molecular conformations and hydrogen bonding in zero, one and two
 dimensions
;
_journal_coeditor_code           YF3117
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              298
_journal_page_last               304
_journal_paper_doi               10.1107/S205322961700273X
_journal_volume                  73
_journal_year                    2017
_chemical_formula_iupac          'C21 H19 Cl F3 N3 O2 S'
_chemical_formula_moiety         'C21 H19 Cl F3 N3 O2 S'
_chemical_formula_sum            'C21 H19 Cl F3 N3 O2 S'
_chemical_formula_weight         469.90
_chemical_name_systematic
1-(4-Chlorophenyl)-5-methylsulfonyl-3-[4-(trifluoromethyl)phenyl]-4,5,6,7-tetrahydro-1<i>H</i>-pyrazolo[4,3-<i>c</i>]pyridine
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.4468(2)
_cell_length_b                   11.4102(4)
_cell_length_c                   34.3009(9)
_cell_measurement_reflns_used    5856
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      29.321
_cell_measurement_theta_min      1.187
_cell_volume                     2131.77(12)
_computing_cell_refinement
;
APEX2 (Bruker, 2012)
;
_computing_data_collection
;
APEX2 (Bruker, 2012)
;
_computing_data_reduction
;
SAINT-Plus (Bruker, 2012)
;
_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
;
SHELXS86 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker Kappa APEXII'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0324
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -3
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -44
_diffrn_reflns_number            15002
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.550
_diffrn_reflns_theta_min         2.144
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.327
_exptl_absorpt_correction_T_max  0.907
_exptl_absorpt_correction_T_min  0.879
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2012)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.464
_exptl_crystal_description       block
_exptl_crystal_F_000             968
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.300
_refine_diff_density_max         0.159
_refine_diff_density_min         -0.218
_refine_ls_abs_structure_details
;
Flack <i>x</i> determined using 1208 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons <i>et al.</i>,  2013)
;
_refine_ls_abs_structure_Flack   0.03(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     309
_refine_ls_number_reflns         4920
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0649
_refine_ls_R_factor_gt           0.0392
_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^)+(0.0426P)^2^+0.0545P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0812
_refine_ls_wR_factor_ref         0.0931
_reflns_number_gt                3587
_reflns_number_total             4920
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            yf3117sup1.cif
_cod_data_source_block           II
_cod_database_code               2020721
_cod_database_fobs_code          2020721
_shelx_estimated_absorpt_t_min   0.880
_shelx_estimated_absorpt_t_max   0.908
_shelx_hkl_checksum              40027
_shelx_res_checksum              32271
_shelxl_version_number           2.014