Isomorphous methyl- and chloro-substituted small heterocyclic analogues obeying the chlorine‒methyl (Cl‒Me) exchange rule
Rajni Swamy, V.; Müller, P.; Srinivasan, N.; Perumal, S.; Krishnakumar, R. V.; Acta Crystallographica Section C 69 (2013) 412–415; doi:10.1107/S0108270113004812

data_2018932
_publ_section_title
;
 Isomorphous methyl- and chloro-substituted small heterocyclic analogues
 obeying the chlorine--methyl (Cl--Me) exchange rule
;
_journal_coeditor_code           TP3020
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              412
_journal_page_last               415
_journal_paper_doi               10.1107/S0108270113004812
_journal_volume                  69
_journal_year                    2013
_chemical_formula_iupac          'C26 H18 F3 N3 O S'
_chemical_formula_moiety         'C26 H18 F3 N3 O S'
_chemical_formula_sum            'C26 H18 F3 N3 O S'
_chemical_formula_weight         477.49
_chemical_name_systematic
'[3-Methyl-4-(4-methylphenyl)-1-phenyl-6-trifluoromethyl-1<i>H</i>-pyrazolo[3,4-<i>b</i>]pyridin-5-yl](thiophen-2-yl)methanone'
_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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                109.211(2)
_cell_angle_beta                 96.105(2)
_cell_angle_gamma                95.676(2)
_cell_formula_units_Z            2
_cell_length_a                   10.0323(4)
_cell_length_b                   10.3715(5)
_cell_length_c                   11.7411(5)
_cell_measurement_reflns_used    10124
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      28.0
_cell_measurement_theta_min      2.1
_cell_volume                     1135.37(9)
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0246
_diffrn_reflns_av_sigmaI/netI    0.0237
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
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_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            25018
_diffrn_reflns_theta_full        30.38
_diffrn_reflns_theta_max         30.38
_diffrn_reflns_theta_min         2.10
_exptl_absorpt_coefficient_mu    0.192
_exptl_absorpt_correction_T_max  0.9889
_exptl_absorpt_correction_T_min  0.8997
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(<i>SADABS</i>; Bruker, 2009)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.397
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             492
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
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_refine_diff_density_min         -0.246
_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
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_refine_ls_number_reflns         6692
_refine_ls_number_restraints     345
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.0683
_refine_ls_R_factor_gt           0.0447
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0550P)^2^+0.2446P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1104
_refine_ls_wR_factor_ref         0.1264
_reflns_number_gt                4773
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_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            tp3020.cif
_cod_data_source_block           I
_cod_original_cell_volume        1135.36(9)
_cod_database_code               2018932
_cod_database_fobs_code          2018932