Asymmetric transfer hydrogenation by synthetic catalysts in cancer cells
James P. C. Coverdale; Isolda Romero-Canelon; Carlos Sanchez-Cano; Guy J. Clarkson; Abraha Habtemariam; Martin Wills; Peter J. Sadler; Nature Chemistry 10 (2018) 347–354; doi:10.1038/nchem.2918

data_1551835
_publ_section_title
;
 Asymmetric transfer hydrogenation by synthetic catalysts in cancer cells
;
_journal_name_full               'Nature Chemistry'
_journal_page_first              347
_journal_page_last               354
_journal_paper_doi               10.1038/nchem.2918
_journal_volume                  10
_journal_year                    2018
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C33 H30 N2 O2 Os S, 2(C H Cl3)'
_chemical_formula_sum            'C35 H32 Cl6 N2 O2 Os S'
_chemical_formula_weight         947.58
_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     direct
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.95923(12)
_cell_length_b                   16.3940(3)
_cell_length_c                   26.8780(5)
_cell_measurement_reflns_used    16542
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      31.3430
_cell_measurement_theta_min      2.5880
_cell_volume                     3507.14(11)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.2833
_diffrn_detector_type            Ruby
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.961
_diffrn_measurement_details
;
  1 omega  -61.00   48.00   1.0000   62.5000
omega____ theta____ kappa____ phi______ frames
    -       15.2579  -77.0000 -150.0000 109

  2 omega  -17.00   91.00   1.0000   62.5000
omega____ theta____ kappa____ phi______ frames
    -       15.2579   77.0000 -180.0000 108

  3 omega  -13.00   88.00   1.0000   62.5000
omega____ theta____ kappa____ phi______ frames
    -       15.2579   57.0000  -30.0000 101

  4 omega   32.00  102.00   1.0000   62.5000
omega____ theta____ kappa____ phi______ frames
    -       15.2579 -178.0000   60.0000 70

  5 omega   32.00   64.00   1.0000   62.5000
omega____ theta____ kappa____ phi______ frames
    -       15.2579 -178.0000 -180.0000 32

  6 omega -105.00  -57.00   1.0000   62.5000
omega____ theta____ kappa____ phi______ frames
    -      -16.1954 -178.0000  -90.0000 48
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Ruby, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0068917000
_diffrn_orient_matrix_UB_12      -0.0295954000
_diffrn_orient_matrix_UB_13      -0.0191387000
_diffrn_orient_matrix_UB_21      0.0041011000
_diffrn_orient_matrix_UB_22      -0.0315497000
_diffrn_orient_matrix_UB_23      0.0180190000
_diffrn_orient_matrix_UB_31      -0.0887589000
_diffrn_orient_matrix_UB_32      0.0008189000
_diffrn_orient_matrix_UB_33      0.0023164000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0614
_diffrn_reflns_av_unetI/netI     0.0596
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.961
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            50022
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.933
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.565
_diffrn_reflns_theta_min         2.591
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    4.189
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84194
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
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    1.795
_exptl_crystal_description       block
_exptl_crystal_F_000             1864
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.02
_refine_diff_density_max         1.170
_refine_diff_density_min         -1.291
_refine_diff_density_rms         0.146
_refine_ls_abs_structure_details
;
 Flack x determined using 3708 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
The Flack parameter was 0.018(4) (Shelx)
The Hooft y parameter was 0.0018(3) (Olex2)

;
_refine_ls_abs_structure_Flack   0.018(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     428
_refine_ls_number_reflns         10950
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0489
_refine_ls_R_factor_gt           0.0361
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0201P)^2^+2.0818P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0581
_refine_ls_wR_factor_ref         0.0623
_reflns_Friedel_coverage         0.749
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.899
_reflns_number_gt                9695
_reflns_number_total             10950
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            nchem.2918-s3.cif
_cod_data_source_block           jc3
_cod_original_cell_volume        3507.14(10)
_cod_database_code               1551835
_chemical_oxdiff_formula         'C20 H20 N2 O2 F6 P Os'
_reflns_odcompleteness_completeness 99.89
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     28.98
_olex2_refinement_description
;

The NH on N11 was located in a difference map and refined with a DFIX 
restraint and given a Uiso 1.5 times the Uequiv of the parent nitrogen. 

1. Fixed Uiso
 At 1.5 times of:
  All C(H,H,H) groups, H11A of C35
 At 1.2 times of:
  H25 of C25, H24 of C24, H32 of C32, H35 of C35, H26 of C26, H28 of C28, H27
  of C27, H33 of C33, H31 of C31, H34 of C34, H01 of C01, H02 of C02, H11 of
  C11, H10 of C10, H7 of C7, H6 of C6, H3 of C3, H21 of C21, H14 of C14, H22 of
  C22, H13 of C13, H15 of C15, H16 of C16, H23 of C23, H20 of C20, H17 of C17,
  H19 of C19, H4 of C4
2. Restrained distances
 N11-H11A
 0.9 with sigma of 0.02
3.a Ternary CH refined with riding coordinates:
 C01(H01), C02(H02), C10(H10), C11(H11)
3.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C7(H7), C13(H13), C14(H14), C15(H15), C16(H16),
 C17(H17), C19(H19), C20(H20), C21(H21), C22(H22), C23(H23), C24(H24), C25(H25),
  C26(H26), C27(H27), C28(H28), C31(H31), C32(H32), C33(H33), C34(H34), C35(H35)
3.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'