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_2018933
_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          'C25 H15 Cl F3 N3 O S'
_chemical_formula_moiety         'C25 H15 Cl F3 N3 O S'
_chemical_formula_sum            'C25 H15 Cl F3 N3 O S'
_chemical_formula_weight         497.91
_chemical_name_systematic
'[4-(4-Chlorophenyl)-3-methyl-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
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_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_cell_length_a                   10.0018(7)
_cell_length_b                   10.3503(8)
_cell_length_c                   11.6309(10)
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_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      28.0
_cell_measurement_theta_min      2.3
_cell_volume                     1125.82(16)
_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 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  graphite
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_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
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_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
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_diffrn_reflns_number            22298
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_diffrn_reflns_theta_max         28.10
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_exptl_absorpt_coefficient_mu    0.311
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_exptl_absorpt_correction_T_min  0.8897
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_exptl_absorpt_process_details   '(<i>SADABS</i>; Bruker, 2009)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.469
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
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_exptl_crystal_size_mid          0.14
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_refine_ls_extinction_method     none
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_refine_ls_number_reflns         5407
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_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0571
_refine_ls_R_factor_gt           0.0370
_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^)+(0.0372P)^2^+0.2614P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
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_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            tp3020.cif
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_cod_database_code               2018933
_cod_database_fobs_code          2018933