Synthesis and anti-tumor activity evaluation of salinomycin C20-<i>O</i>-alkyl/benzyl oxime derivatives.
Li, Bo; Wu, Jun; Tang, Lei; Lian, Xu; Li, Zhongwen; Duan, Wenfang; Qin, Tong; Zhao, Xintong; Hu, Yuhua; Zhang, Chi; Li, Tianlei; Hao, Jie; Zhang, Wenxuan; Zhang, Jihong; Wu, Song; Organic & biomolecular chemistry 20 (2022) 870–876; doi:10.1039/d1ob02292j

data_7158472
_publ_section_title
;
 Synthesis and anti-tumor activity evaluation of salinomycin
 C20-<i>O</i>-alkyl/benzyl oxime derivatives.
;
_journal_issue                   4
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              870
_journal_page_last               876
_journal_paper_doi               10.1039/d1ob02292j
_journal_volume                  20
_journal_year                    2022
_chemical_absolute_configuration rm
_chemical_formula_moiety         'C49 H75 N O11, C2 H3 N'
_chemical_formula_sum            'C51 H78 N2 O11'
_chemical_formula_weight         895.15
_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   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2016-03-14
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_audit_update_record
;
2020-06-30 deposited with the CCDC.	2021-12-14 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.28331(11)
_cell_length_b                   15.0300(2)
_cell_length_c                   33.3759(5)
_cell_measurement_reflns_used    18272
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      66.6800
_cell_measurement_theta_min      4.4890
_cell_volume                     5158.52(12)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41k (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41k (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41k (Rigaku OD, 2015)'
_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    'ShelXS (Sheldrick, 2008)'
_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 0.980
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w   -118.00 -85.00   1.00    1.02    --  -42.20-161.00 -77.00   33
  2  \w    -23.00  70.00   1.00    1.02    --   42.20 -57.00-150.00   93
  3  \w     33.00  59.00   1.00    1.02    --   42.20  38.00-180.00   26
  4  \w     86.00 115.00   1.00    1.02    --   42.20  38.00-180.00   29
  5  \w     73.00 103.00   1.00    4.08    --   92.50 -93.00 -29.00   30
  6  \w     16.00  64.00   1.00    4.08    --   92.50 -77.00-150.00   48
  7  \w     55.00  81.00   1.00    4.08    --   92.50 -83.00  35.19   26
  8  \w     29.00  96.00   1.00    4.08    --   92.50-125.00-180.00   67
  9  \w     72.00 165.00   1.00    4.08    --   92.50  61.00 120.00   93
 10  \w     20.00  60.00   1.00    4.08    --   92.50-125.00 -60.00   40
 11  \w     20.00  45.00   1.00    4.08    --   92.50 -95.00-150.00   25
 12  \w     27.00  53.00   1.00    4.08    --   92.50 -95.00-120.00   26
 13  \w     23.00  78.00   1.00    4.08    --   92.50 -61.00 -30.00   55
 14  \w     23.00  48.00   1.00    4.08    --   92.50-125.00 -30.00   25
 15  \w     33.00  70.00   1.00    4.08    --   92.50 -77.00  60.00   37
 16  \w     50.00  76.00   1.00    4.08    --   92.50 -45.00-150.00   26
 17  \w     40.00  83.00   1.00    4.08    --   92.50 -95.00  60.00   43
 18  \w     59.00  85.00   1.00    4.08    --   92.50 -61.00-180.00   26
 19  \w     17.00 108.00   1.00    4.08    --   92.50 -77.00-120.00   91
 20  \w     54.00  93.00   1.00    4.08    --   92.50-125.00-120.00   39
 21  \w     65.00 105.00   1.00    4.08    --   92.50 -30.00 -90.00   40
 22  \w     19.00  45.00   1.00    4.08    --   92.50 -93.00 -29.00   26
 23  \w     71.00  96.00   1.00    4.08    --   92.50 -77.00-150.00   25
 24  \w     74.00 131.00   1.00    4.08    --   92.50 125.00   0.00   57
 25  \w     68.00 117.00   1.00    4.08    --   92.50 -93.00  28.78   49
 26  \w     59.00  84.00   1.00    4.08    --   92.50 -95.00   0.00   25
 27  \w     82.00 108.00   1.00    4.08    --   92.50  61.00 150.00   26
 28  \w     77.00 106.00   1.00    4.08    --   92.50 -61.00   0.00   29
 29  \w     12.00  57.00   1.00    4.08    --   92.50 -93.00  28.78   45
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0162156000
_diffrn_orient_matrix_UB_12      -0.0459633000
_diffrn_orient_matrix_UB_13      0.0409606000
_diffrn_orient_matrix_UB_21      -0.0315744000
_diffrn_orient_matrix_UB_22      0.0904991000
_diffrn_orient_matrix_UB_23      0.0193967000
_diffrn_orient_matrix_UB_31      -0.1454855000
_diffrn_orient_matrix_UB_32      -0.0144407000
_diffrn_orient_matrix_UB_33      -0.0087571000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0306
_diffrn_reflns_av_unetI/netI     0.0219
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_number            42181
_diffrn_reflns_point_group_measured_fraction_full 0.978
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         66.825
_diffrn_reflns_theta_min         3.225
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance Ultra (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.646
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.30717
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41k (Rigaku Oxford Diffraction, 2015)
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    1.153
_exptl_crystal_description       block
_exptl_crystal_F_000             1944
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.133
_refine_diff_density_min         -0.178
_refine_diff_density_rms         0.027
_refine_ls_abs_structure_details
;
 Flack x determined using 3453 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.07(5)
_refine_ls_extinction_coef       0.00081(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     592
_refine_ls_number_reflns         9137
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0370
_refine_ls_R_factor_gt           0.0327
_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^)+(0.0481P)^2^+0.2890P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0834
_refine_ls_wR_factor_ref         0.0873
_reflns_Friedel_coverage         0.787
_reflns_Friedel_fraction_full    0.976
_reflns_Friedel_fraction_max     0.996
_reflns_number_gt                8310
_reflns_number_total             9137
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ob02292j2.cif
_cod_data_source_block           lb0302
_cod_depositor_comments          'Adding full bibliography for 7158472.cif.'
_cod_original_cell_volume        5158.52(11)
_cod_database_code               7158472
_shelxl_version_number           2013-2
_chemical_oxdiff_formula         'C1 H1 O1 N1'
_reflns_odcompleteness_completeness 99.44
_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:
 C30(H30), C50(H50), C54(H54), C27(H27), C12(H12), C51(H51), C23(H23),
 C29(H29), C26(H26), C55(H55), C16(H16), C31(H31), C25(H25)
2.b Secondary CH2 refined with riding coordinates:
 C36(H36A,H36B), C24(H24A,H24B), C10(H10A,H10B), C53(H53A,H53B), C14(H14A,
 H14B), C13(H13A,H13B), C52(H52A,H52B), C9(H9A,H9B), C18(H18A,H18B), C59(H59A,
 H59B), C42(H42A,H42B)
2.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C48(H48), C47(H47), C44(H44), C46(H46), C45(H45)
2.d Idealised Me refined as rotating group:
 C34(H34A,H34B,H34C), C38(H38A,H38B,H38C), C32(H32A,H32B,H32C), C21(H21A,H21B,
 H21C), C20(H20A,H20B,H20C), C37(H37A,H37B,H37C), C19(H19A,H19B,H19C), C39(H39A,
 H39B,H39C), C60(H60A,H60B,H60C), C61(H61A,H61B,H61C), C1(H1A,H1B,H1C)
2.e Idealised tetrahedral OH refined as rotating group:
 O17(H17), O33(H33), O57(H57)
;
_olex2_date_sample_data_collection 2016-03-02
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 3.550
_oxdiff_exptl_absorpt_empirical_full_min 0.813