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_7157223
_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_formula_moiety         'C19 H14 F5 Fe N O S'
_chemical_formula_sum            'C19 H14 F5 Fe N O S'
_chemical_formula_weight         455.22
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_audit_block_doi                 10.5517/ccdc.csd.cc1phmkc
_audit_creation_date             2015-05-07
_audit_creation_method
;
Olex2 1.2
(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                 102.331(4)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   28.9645(11)
_cell_length_b                   9.2222(4)
_cell_length_c                   13.5088(6)
_cell_measurement_reflns_used    9295
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.4990
_cell_measurement_theta_min      2.3090
_cell_volume                     3525.2(3)
_computing_cell_refinement
;
CrystalClear-SM Expert 2.1 b31 (Rigaku, 2014)
;
_computing_data_collection
;
CrystalClear-SM Expert 3.1 b27 (Rigaku, 2013)
;
_computing_data_reduction
;
CrystalClear-SM Expert 2.1 b31 (Rigaku, 2014)
;
_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 0.999
_diffrn_measurement_details
;
  1 omega -106.00   74.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.0000    0.0000   60.0000 180

  2 omega  -60.00   23.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.0000  -72.0000 -150.0000 83

  3 omega  -70.00   23.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.0000  -72.0000    0.0000 93

  4 omega  -29.00    5.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.0000   72.0000  120.0000 34

  5 omega  -49.00  -34.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.0000  -72.0000 -180.0000 15

  6 omega  -11.00    5.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.0000   72.0000  -90.0000 16

  7 omega  -32.00   74.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.0000   72.0000 -120.0000 106

  8 omega  -74.00    8.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.0000  -72.0000  120.0000 82
;
_diffrn_measurement_device       'four-circle \k diffractometer'
_diffrn_measurement_device_type  Kat
_diffrn_measurement_method       'profile data from \w-scans'
_diffrn_measurement_specimen_support 'MiTeGen MicroMesh'
_diffrn_orient_matrix_UB_11      0.0040678000
_diffrn_orient_matrix_UB_12      0.0528199000
_diffrn_orient_matrix_UB_13      -0.0353382000
_diffrn_orient_matrix_UB_21      0.0151652000
_diffrn_orient_matrix_UB_22      -0.0489995000
_diffrn_orient_matrix_UB_23      -0.0181571000
_diffrn_orient_matrix_UB_31      -0.0195410000
_diffrn_orient_matrix_UB_32      -0.0269103000
_diffrn_orient_matrix_UB_33      -0.0362094000
_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  0.0832
_diffrn_reflns_av_unetI/netI     0.0657
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       37
_diffrn_reflns_limit_h_min       -37
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            24695
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.556
_diffrn_reflns_theta_min         2.323
_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    1.035
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.65175
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrystalClear-SM Expert 2.1 b31 (Rigaku, 2014)
;
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.715
_exptl_crystal_description       plate
_exptl_crystal_F_000             1840
_exptl_crystal_size_max          0.06
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.496
_refine_diff_density_min         -0.354
_refine_diff_density_rms         0.084
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     256
_refine_ls_number_reflns         4053
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.011
_refine_ls_R_factor_all          0.0890
_refine_ls_R_factor_gt           0.0506
_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^)+(0.0491P)^2^+1.9280P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0967
_refine_ls_wR_factor_ref         0.1089
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2809
_reflns_number_total             4053
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7ob02289a2.cif
_cod_data_source_block           Z-164
_cod_database_code               7157223
_chemical_oxdiff_formula         'C19 H14 F5 Fe N O S'
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2. Restrained distances
 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), C14(H14),
 C15(H15), C16(H16), C17(H17), C18(H18), C19(H19)
;
_shelx_res_checksum              25885
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2015-05-28
_olex2_date_sample_submission    2015-03-24
_olex2_submission_original_sample_id Exp106-fr1
_olex2_submission_special_instructions 'No special instructions were received'