Synthesis of kinase inhibitors containing a pentafluorosulfanyl moiety.
Sansook, Supojjanee; Ocasio, Cory A.; Day, Iain J.; Tizzard, Graham J.; Coles, Simon J.; Fedorov, Oleg; Bennett, James M.; Elkins, Jonathan M.; Spencer, John; Organic & biomolecular chemistry 15 (2017) 8655–8660; doi:10.1039/c7ob02289a

data_7157220
_publ_section_title
;
 Synthesis of kinase inhibitors containing a pentafluorosulfanyl moiety.
;
_journal_issue                   40
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              8655
_journal_page_last               8660
_journal_paper_doi               10.1039/c7ob02289a
_journal_volume                  15
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C13 H9 F5 N2 O S'
_chemical_formula_sum            'C13 H9 F5 N2 O S'
_chemical_formula_weight         336.28
_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'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_audit_block_doi                 10.5517/ccdc.csd.cc1phmg8
_audit_creation_date             2015-03-04
_audit_creation_method
;
Olex2 1.2-alpha
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_audit_update_record
;
2017-07-24 deposited with the CCDC.
2017-11-29 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.07381(17)
_cell_length_b                   10.7631(3)
_cell_length_c                   19.4480(5)
_cell_measurement_reflns_used    12604
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.5610
_cell_measurement_theta_min      2.0610
_cell_volume                     1271.37(6)
_computing_cell_refinement
'CrysAlisPro, Agilent Technologies, Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET) (compiled Aug 13 2014,18:06:01)'
_computing_data_collection       'CrystalClear-SM Expert 3.1 b27 (Rigaku, 2013)'
_computing_data_reduction
'CrysAlisPro, Agilent Technologies, Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET) (compiled Aug 13 2014,18:06:01)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type            'Rigaku HG Saturn724+ (2x2 bin mode)'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details
;
  1 omega -106.00   58.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.0000   -8.0000   16.0000 164

  2 omega  -76.00   23.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.0000  -72.0000  -82.0000 99

  3 omega  -61.00   23.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.0000  -72.0000  114.0000 84

  4 omega -106.00  -31.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.0000  -40.0000   16.0000 75

  5 omega  -22.00   -7.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.0000   56.0000 -115.0000 15

  6 omega -106.00    9.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.0000  -72.0000 -148.0000 115
;
_diffrn_measurement_device       'four-circle \k diffractometer'
_diffrn_measurement_device_type  'Rigaku AFC12 (Right)'
_diffrn_measurement_method       'profile data from \w-scans'
_diffrn_measurement_specimen_support 'MiTeGen MicroMesh'
_diffrn_orient_matrix_UB_11      0.0382562000
_diffrn_orient_matrix_UB_12      -0.0546962000
_diffrn_orient_matrix_UB_13      -0.0165206000
_diffrn_orient_matrix_UB_21      -0.0058731000
_diffrn_orient_matrix_UB_22      0.0304270000
_diffrn_orient_matrix_UB_23      -0.0322730000
_diffrn_orient_matrix_UB_31      0.1101620000
_diffrn_orient_matrix_UB_32      0.0206116000
_diffrn_orient_matrix_UB_33      0.0040338000
_diffrn_radiation_collimation    0.3
_diffrn_radiation_monochromator  'Confocal mirrors, HF Varimax'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0310
_diffrn_reflns_av_unetI/netI     0.0198
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            16814
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.556
_diffrn_reflns_theta_min         2.094
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           55.0
_diffrn_source_power             2.475
_diffrn_source_target            Mo
_diffrn_source_type              'Rotating Anode'
_diffrn_source_voltage           45.0
_exptl_absorpt_coefficient_mu    0.320
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86039
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'CrysAlisPro, Agilent Technologies, Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET) (compiled Aug 13 2014,18:06:01) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.'
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.757
_exptl_crystal_description       block
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.165
_exptl_crystal_size_mid          0.085
_exptl_crystal_size_min          0.045
_refine_diff_density_max         0.443
_refine_diff_density_min         -0.250
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details
;
 Flack x determined using 1126 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.03(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     205
_refine_ls_number_reflns         2916
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0278
_refine_ls_R_factor_gt           0.0258
_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^)+(0.0356P)^2^+0.4116P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0640
_refine_ls_wR_factor_ref         0.0649
_reflns_Friedel_coverage         0.710
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                2788
_reflns_number_total             2916
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7ob02289a2.cif
_cod_data_source_block           162
_cod_original_cell_volume        1271.38(6)
_cod_database_code               7157220
_chemical_oxdiff_formula         'C13 H9 F5 N2 O S'
_reflns_odcompleteness_completeness 99.88
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.49
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2. Restrained distances
 N2-H2 = N1-H1
 0.88 with sigma of 0.02
3.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C6(H6), C7(H7), C9(H9), C11(H11), C12(H12), C13(H13)
;
_shelx_res_checksum              85013
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2015-03-03
_olex2_date_sample_submission    2015-02-27
_olex2_submission_original_sample_id Exp.108
_olex2_submission_special_instructions 'No special instructions were received'