Structure-activity & structure-toxicity relationship study of salinomycin diastereoisomers and their benzoylated derivatives.
Zhang, Wenxuan; Wu, Jun; Li, Bo; Wu, Hongna; Wang, Liu; Hao, Jie; Wu, Song; Zhou, Qi; Organic & biomolecular chemistry 14 (2016) 2840–2845; doi:10.1039/c5ob02303c

data_7154896
_publ_section_title
;
 Structure-activity &amp; structure-toxicity relationship study of
 salinomycin diastereoisomers and their benzoylated derivatives.
;
_journal_issue                   10
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              2840
_journal_page_last               2845
_journal_paper_doi               10.1039/c5ob02303c
_journal_volume                  14
_journal_year                    2016
_chemical_formula_moiety         'C55 H88 O11 Si'
_chemical_formula_sum            'C55 H88 O11 Si'
_chemical_formula_weight         953.34
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2015-11-03
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_audit_update_record
;
2015-11-03 deposited with the CCDC.
2016-01-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.8798(18)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   12.1784(3)
_cell_length_b                   10.4550(2)
_cell_length_c                   22.4818(4)
_cell_measurement_reflns_used    14747
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      66.6470
_cell_measurement_theta_min      3.6920
_cell_volume                     2820.05(10)
_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
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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, 2015)'
_computing_structure_solution
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4674
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
  1 omega  -98.00  -18.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.6415  125.0000  -30.0000 80

  2 omega  -33.00   66.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       41.6415  -38.0000  150.0000 99

  3 omega   17.00  116.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       41.6415   38.0000  -60.0000 99

  4 omega  -33.00   66.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       41.6415  -38.0000   30.0000 99

  5 omega   17.00  116.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       41.6415   38.0000    0.0000 99

  6 omega   19.00   75.00   1.0000    1.5600
omega____ theta____ kappa____ phi______ frames
    -       92.5000  -45.0000   30.0000 56

  7 omega   66.00  116.00   1.0000    1.5600
omega____ theta____ kappa____ phi______ frames
    -       92.5000   30.0000  -60.0000 50

  8 omega   15.00   69.00   1.0000    1.5600
omega____ theta____ kappa____ phi______ frames
    -       92.5000  -82.0000  128.4899 54

  9 omega   56.00   96.00   1.0000    1.5600
omega____ theta____ kappa____ phi______ frames
    -       92.5000 -125.0000  150.0000 40

 10 omega   20.00   45.00   1.0000    1.5600
omega____ theta____ kappa____ phi______ frames
    -       92.5000 -125.0000  150.0000 25

 11 omega   64.00   94.00   1.0000    1.5600
omega____ theta____ kappa____ phi______ frames
    -       92.5000   61.0000  -60.0000 30

 12 omega  104.00  163.00   1.0000    1.5600
omega____ theta____ kappa____ phi______ frames
    -       92.5000   61.0000  -60.0000 59

 13 omega   67.00  106.00   1.0000    1.5600
omega____ theta____ kappa____ phi______ frames
    -       92.5000   30.0000  -30.0000 39

 14 omega  126.00  153.00   1.0000    1.5600
omega____ theta____ kappa____ phi______ frames
    -       92.5000   30.0000  -30.0000 27

 15 omega   87.00  166.00   1.0000    1.5600
omega____ theta____ kappa____ phi______ frames
    -       92.5000   30.0000   90.0000 79

 16 omega   66.00  121.00   1.0000    1.5600
omega____ theta____ kappa____ phi______ frames
    -       92.5000   61.0000  -30.0000 55

 17 omega   23.00   68.00   1.0000    1.5600
omega____ theta____ kappa____ phi______ frames
    -       92.5000  -45.0000  120.0000 45

 18 omega   32.00   62.00   1.0000    1.5600
omega____ theta____ kappa____ phi______ frames
    -       92.5000  -30.0000  -60.0000 30

 19 omega  125.00  161.00   1.0000    1.5600
omega____ theta____ kappa____ phi______ frames
    -       92.5000   61.0000  -30.0000 36

 20 omega   20.00   74.00   1.0000    1.5600
omega____ theta____ kappa____ phi______ frames
    -       92.5000  -45.0000  -90.0000 54

 21 omega   35.00   77.00   1.0000    1.5600
omega____ theta____ kappa____ phi______ frames
    -       92.5000 -125.0000   90.0000 42

 22 omega   16.00   68.00   1.0000    1.5600
omega____ theta____ kappa____ phi______ frames
    -       92.5000  -30.0000 -150.0000 52

 23 omega  132.00  164.00   1.0000    1.5600
omega____ theta____ kappa____ phi______ frames
    -       92.5000   30.0000  150.0000 32

 24 omega   16.00   48.00   1.0000    1.5600
omega____ theta____ kappa____ phi______ frames
    -       92.5000  -30.0000   60.0000 32

 25 omega   63.00   98.00   1.0000    1.5600
omega____ theta____ kappa____ phi______ frames
    -       92.5000   61.0000    0.0000 35

 26 omega  119.00  150.00   1.0000    1.5600
omega____ theta____ kappa____ phi______ frames
    -       92.5000   61.0000    0.0000 31

 27 omega   20.00   45.00   1.0000    1.5600
omega____ theta____ kappa____ phi______ frames
    -       92.5000 -125.0000  120.0000 25

 28 omega   70.00  114.00   1.0000    1.5600
omega____ theta____ kappa____ phi______ frames
    -       92.5000   15.0000  -60.0000 44

 29 omega   44.00   72.00   1.0000    1.5600
omega____ theta____ kappa____ phi______ frames
    -       92.5000  -45.0000 -120.0000 28

 30 omega   50.00   76.00   1.0000    1.5600
omega____ theta____ kappa____ phi______ frames
    -       92.5000  -45.0000   90.0000 26

 31 omega   78.00  104.00   1.0000    1.5600
omega____ theta____ kappa____ phi______ frames
    -       92.5000  -82.0000  128.4899 26

 32 omega  119.00  145.00   1.0000    1.5600
omega____ theta____ kappa____ phi______ frames
    -       92.5000   22.0000   62.9413 26

 33 omega  127.00  162.00   1.0000    1.5600
omega____ theta____ kappa____ phi______ frames
    -       92.5000   15.0000  -60.0000 35

 34 omega   65.00  111.00   1.0000    1.5600
omega____ theta____ kappa____ phi______ frames
    -       92.5000   77.0000   60.0000 46

 35 omega  114.00  145.00   1.0000    1.5600
omega____ theta____ kappa____ phi______ frames
    -       92.5000   77.0000   60.0000 31

 36 omega   15.00   57.00   1.0000    1.5600
omega____ theta____ kappa____ phi______ frames
    -       92.5000  -95.0000  150.0000 42

 37 omega  100.00  158.00   1.0000    1.5600
omega____ theta____ kappa____ phi______ frames
    -       92.5000   45.0000  120.0000 58

 38 omega   74.00  100.00   1.0000    1.5600
omega____ theta____ kappa____ phi______ frames
    -       92.5000   30.0000 -150.0000 26

 39 omega  138.00  168.00   1.0000    1.5600
omega____ theta____ kappa____ phi______ frames
    -       92.5000   30.0000 -150.0000 30

 40 omega   57.00   83.00   1.0000    1.5600
omega____ theta____ kappa____ phi______ frames
    -       92.5000  -77.0000   60.0000 26

 41 omega   93.00  120.00   1.0000    1.5600
omega____ theta____ kappa____ phi______ frames
    -       92.5000  -77.0000   60.0000 27

 42 omega   36.00   71.00   1.0000    1.5600
omega____ theta____ kappa____ phi______ frames
    -       92.5000 -125.0000   30.0000 35

 43 omega   94.00  120.00   1.0000    1.5600
omega____ theta____ kappa____ phi______ frames
    -       92.5000   45.0000  -30.0000 26

 44 omega  119.00  160.00   1.0000    1.5600
omega____ theta____ kappa____ phi______ frames
    -       92.5000   45.0000   30.0000 41

 45 omega   87.00  113.00   1.0000    1.5600
omega____ theta____ kappa____ phi______ frames
    -       92.5000   61.0000 -120.0000 26

 46 omega  115.00  141.00   1.0000    1.5600
omega____ theta____ kappa____ phi______ frames
    -       92.5000   61.0000 -120.0000 26

 47 omega   19.00   46.00   1.0000    1.5600
omega____ theta____ kappa____ phi______ frames
    -       92.5000  -30.0000  -90.0000 27

 48 omega   53.00   79.00   1.0000    1.5600
omega____ theta____ kappa____ phi______ frames
    -       92.5000  -61.0000 -150.0000 26

 49 omega   20.00   59.00   1.0000    1.5600
omega____ theta____ kappa____ phi______ frames
    -       92.5000  -61.0000   60.0000 39

 50 omega   67.00   98.00   1.0000    1.5600
omega____ theta____ kappa____ phi______ frames
    -       92.5000   30.0000   60.0000 31

 51 omega   95.00  121.00   1.0000    1.5600
omega____ theta____ kappa____ phi______ frames
    -       92.5000  -84.0000  -64.2061 26

 52 omega   57.00   87.00   1.0000    1.5600
omega____ theta____ kappa____ phi______ frames
    -       92.5000   22.0000   62.9413 30
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.1185217000
_diffrn_orient_matrix_UB_12      0.0217484000
_diffrn_orient_matrix_UB_13      0.0354934000
_diffrn_orient_matrix_UB_21      0.0459079000
_diffrn_orient_matrix_UB_22      -0.1000156000
_diffrn_orient_matrix_UB_23      -0.0397198000
_diffrn_orient_matrix_UB_31      0.0190467000
_diffrn_orient_matrix_UB_32      0.1059079000
_diffrn_orient_matrix_UB_33      -0.0446773000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0390
_diffrn_reflns_av_unetI/netI     0.0221
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            41478
_diffrn_reflns_point_group_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         67.001
_diffrn_reflns_theta_min         3.684
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'Enhance Ultra (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.803
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.71008
_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.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.123
_exptl_crystal_description       block
_exptl_crystal_F_000             1040
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.349
_refine_diff_density_min         -0.178
_refine_diff_density_rms         0.032
_refine_ls_abs_structure_details
;
 Flack x determined using 3503 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.022(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     619
_refine_ls_number_reflns         10003
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.0541
_refine_ls_R_factor_gt           0.0447
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[\s^2^(Fo^2^)+(0.0787P)^2^+0.2039P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1202
_refine_ls_wR_factor_ref         0.1312
_reflns_Friedel_coverage         0.878
_reflns_Friedel_fraction_full    0.975
_reflns_Friedel_fraction_max     0.989
_reflns_number_gt                8405
_reflns_number_total             10003
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5ob02303c2.cif
_cod_data_source_block           zwx-31
_cod_depositor_comments          'Adding full bibliography for 7154896.cif.'
_cod_original_cell_volume        2820.06(10)
_cod_database_code               7154896
_shelxl_version_number           2013-2
_chemical_oxdiff_formula         'C1 H1 O1 N1'
_reflns_odcompleteness_completeness 99.70
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C5(H5), C11(H11), C46(H46), C12(H12), C15(H15), C16(H16), C42(H42), C29(H29),
 C45(H45), C47(H47), C14(H14), C33(H33), C10(H10), C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C30(H30a,H30b), C21(H21a,H21b), C31(H31a,H31b), C25(H25a,H25b), C26(H26a,
 H26b), C43(H43a,H43b), C50(H50a,H50b), C44(H44a,H44b), C54(H54a,H54b),
 C36(H36a,H36b), C9(H9a,H9b), C52(H52a,H52b)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C64(H64), C65(H65), C61(H61), C62(H62), C63(H63)
2.d Idealised Me refined as rotating group:
 C35(H35a,H35b,H35c), C17(H17a,H17b,H17c), C34(H34a,H34b,H34c), C59(H59a,H59b,
 H59c), C23(H23a,H23b,H23c), C57(H57a,H57b,H57c), C19(H19a,H19b,H19c), C37(H37a,
 H37b,H37c), C56(H56a,H56b,H56c), C58(H58a,H58b,H58c), C22(H22a,H22b,H22c),
 C1(H1a,H1b,H1c), C1AA(H1Aa,H1Ab,H1Ac), C0AA(H0Aa,H0Ab,H0Ac)
2.e Idealised tetrahedral OH refined as rotating group:
 O18(H18)
;
_olex2_date_sample_data_collection 2015-06-08
_olex2_submission_special_instructions 'No special instructions were received'