Models of the putative antimony(V)-diolate motifs in antileishmanial pentavalent antimonial drugs.
Lindquist-Kleissler, Brent; Johnstone, Timothy C.; Dalton transactions (Cambridge, England : 2003)  (2023) –; doi:10.1039/d3dt01623d

data_7713253
_publ_section_title
;
 Models of the putative antimony(V)-diolate motifs in antileishmanial
 pentavalent antimonial drugs.
;
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_paper_doi               10.1039/d3dt01623d
_journal_year                    2023
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C27 H31 O2 Sb'
_chemical_formula_sum            'C27 H31 O2 Sb'
_chemical_formula_weight         509.27
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2022-12-06
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2023-05-27 deposited with the CCDC.	2023-06-20 downloaded from the CCDC.
;
_cell_angle_alpha                76.082(2)
_cell_angle_beta                 78.930(2)
_cell_angle_gamma                74.721(2)
_cell_formula_units_Z            2
_cell_length_a                   8.8969(2)
_cell_length_b                   9.3354(2)
_cell_length_c                   15.1475(4)
_cell_measurement_reflns_used    20738
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      76.6710
_cell_measurement_theta_min      2.9970
_cell_volume                     1166.83(5)
_computing_cell_refinement       'CrysAlisPro 1.171.42.64a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.64a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.64a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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      6.00  31.00   0.50    0.05    --   24.00  71.00 164.47   50
  2  \w      6.00  31.00   0.50    0.05    --   24.00  71.00  26.17   50
  3  \w     -6.00  19.00   0.50    0.05    --   16.00  80.00 -76.84   50
  4  \w     17.00  42.00   0.50    0.05    --   32.00  63.00 -14.76   50
  5  \w     17.00  42.00   0.50    0.05    --   32.00  63.00 -68.53   50
  6  \w      6.00  31.00   0.50    0.05    --   24.00  71.00-117.28   50
  7  \w     36.00  72.00   0.50    0.05    --   49.41  64.00-114.00   72
  8  \w     88.00 115.00   0.50    0.05    --   49.41  64.00-114.00   54
  9  \w     22.00  47.00   0.50    0.05    --   36.00  61.00   2.81   50
 10  \w     22.00  47.00   0.50    0.05    --   36.00  61.00-121.94   50
 11  \w     22.00  47.00   0.50    0.05    --   36.00  61.00  43.07   50
 12  \w     22.00  47.00   0.50    0.05    --   36.00  61.00  98.57   50
 13  \w     22.00  47.00   0.50    0.05    --   36.00  60.00 135.68   50
 14  \w     22.00  47.00   0.50    0.05    --   36.00  61.00 122.72   50
 15  \w     38.00  64.00   0.50    0.05    --   49.41  56.00  41.57   52
 16  \w     25.00  50.00   0.50    0.05    --   36.00  59.00-166.22   50
 17  \w    -17.00   8.00   0.50    0.05    --   12.00  94.00-159.33   50
 18  \w    -40.00   2.00   0.50    0.05    --  -49.41  64.00-114.00   84
 19  \w    -68.00 -42.00   0.50    0.22    --  -84.25  64.00-114.00   52
 20  \w    -42.00 -16.00   0.50    0.22    --  -84.25  38.00  30.00   52
 21  \w    -41.00 -16.00   0.50    0.22    --  -84.25  38.00  90.00   50
 22  \w     -6.00  20.00   0.50    0.05    --   16.00  83.00  73.03   52
 23  \w    -20.00  52.00   0.50    0.05    --   49.41 -64.00 109.00  144
 24  \w    -37.00 -12.00   0.50    0.05    --  -28.00 -67.00 -47.33   50
 25  \w    -53.00 -28.00   0.50    0.05    --  -40.00 -59.00  19.78   50
 26  \w    -71.00 -34.00   0.50    0.05    --  -49.41 -64.00 109.00   74
 27  \w   -102.00 -69.00   0.50    0.22    --  -84.25 -64.00 109.00   66
 28  \w   -155.00-127.00   0.50    0.22    --  -84.25 -64.00 109.00   56
 29  \w   -154.00-128.00   0.50    0.22    --  -84.25 -57.00  60.00   52
 30  \w   -119.00 -84.00   0.50    0.22    --  -84.25 -57.00  60.00   70
 31  \w    -90.00 -63.00   0.50    0.22    --  -76.00 -56.00 156.91   54
 32  \w    -88.00 -63.00   0.50    0.22    --  -76.00 -56.00 100.18   50
 33  \w    -71.00 -43.00   0.50    0.05    --  -56.00 -56.00  57.76   56
 34  \w   -102.00 -76.00   0.50    0.22    --  -84.25 -56.00  66.36   52
 35  \w    -91.00 -65.00   0.50    0.22    --  -76.00 -56.00  27.20   52
 36  \w    -94.00 -63.00   0.50    0.22    --  -76.00 -56.00 -31.91   62
 37  \w    -99.00 -66.00   0.50    0.22    --  -76.00 -56.00-110.30   66
 38  \w   -131.00-101.00   0.50    0.22    --  -84.25 -55.00-177.61   60
 39  \w   -153.00-127.00   0.50    0.22    --  -84.25 -56.00  66.36   52
 40  \w    -81.00 -56.00   0.50    0.22    --  -68.00 -55.00 162.27   50
 41  \w    -83.00 -56.00   0.50    0.22    --  -68.00 -55.00 114.98   54
 42  \w   -101.00 -76.00   0.50    0.22    --  -84.25 -55.00 132.09   50
 43  \w   -144.00-116.00   0.50    0.22    --  -84.25 -55.00 132.09   56
 44  \w   -147.00-121.00   0.50    0.22    --  -84.25 -55.00  24.75   52
 45  \w    -74.00 -48.00   0.50    0.05    --  -60.00 -55.00  36.90   52
 46  \w   -101.00 -69.00   0.50    0.05    --  -52.00 -55.00-126.35   64
 47  \w    -65.00 -40.00   0.50    0.05    --  -52.00 -55.00-126.35   50
 48  \w    -94.00 -64.00   0.50    0.22    --  -76.00 -55.00-129.66   60
 49  \w   -100.00 -72.00   0.50    0.22    --  -84.25 -55.00-156.96   56
 50  \w   -103.00 -72.00   0.50    0.22    --  -84.25 -55.00 -85.38   62
 51  \w    -97.00 -72.00   0.50    0.22    --  -84.25 -55.00-177.61   50
 52  \w   -151.00-125.00   0.50    0.22    --  -84.25 -55.00 -85.38   52
 53  \w   -156.00-119.00   0.50    0.22    --  -84.25 -54.00 -55.28   74
 54  \w    -94.00 -56.00   0.50    0.22    --  -68.00 -54.00 -60.49   76
 55  \w   -101.00 -72.00   0.50    0.22    --  -84.25 -54.00 -15.05   58
 56  \w    -86.00 -60.00   0.50    0.22    --  -72.00 -54.00  -6.40   52
 57  \w    -97.00 -72.00   0.50    0.22    --  -84.25 -55.00  24.75   50
 58  \w    -86.00 -60.00   0.50    0.22    --  -72.00 -54.00  31.97   52
 59  \w    -99.00 -72.00   0.50    0.22    --  -84.25 -55.00  82.92   54
 60  \w   -107.00 -73.00   0.50    0.22    --  -84.25 -53.00 160.73   68
 61  \w   -148.00-121.00   0.50    0.22    --  -84.25 -55.00  82.92   54
 62  \w   -143.00-118.00   0.50    0.22    --  -84.25 -54.00 -15.05   50
 63  \w   -103.00 -77.00   0.50    0.22    --  -84.25 -51.00  -0.70   52
 64  \w    -97.00 -72.00   0.50    0.22    --  -84.25 -54.00 -55.28   50
 65  \w    -86.00 -49.00   0.50    0.05    --  -60.00 -52.00 -97.62   74
 66  \w   -100.00 -75.00   0.50    0.22    --  -84.25 -53.00-130.35   50
 67  \w   -113.00 -80.00   0.50    0.22    --  -84.25 -49.00-144.35   66
 68  \w   -156.00-117.00   0.50    0.22    --  -84.25 -53.00-130.35   78
 69  \w   -145.00-120.00   0.50    0.22    --  -84.25 -47.00 -80.77   50
 70  \w   -100.00 -74.00   0.50    0.22    --  -84.25 -47.00 -80.77   52
 71  \w   -118.00 -93.00   0.50    0.05    --  -49.41-125.00  60.00   50
 72  \w   -118.00 -93.00   0.50    0.05    --  -49.41-125.00  90.00   50
 73  \w     37.00  66.00   0.50    0.22    --  105.75 -57.00-120.00   58
 74  \w     34.00  66.00   0.50    0.22    --  105.75 -57.00 -90.00   64
 75  \w     37.00  65.00   0.50    0.22    --  105.75 -57.00 -60.00   56
 76  \w     35.00 101.00   0.50    0.22    --  105.75 -77.00  30.00  132
 77  \w     43.00  76.00   0.50    0.22    --  105.75 -64.00 109.00   66
 78  \w    100.00 168.00   0.50    0.22    --  105.75  77.00-150.00  136
 79  \w    135.00 177.00   0.50    0.22    --  105.75  64.00-114.00   84
 80  \w    107.00 146.00   0.50    0.22    --  105.75  77.00-120.00   78
 81  \w     92.00 118.00   0.50    0.22    --  105.75  64.00-114.00   52
 82  \w    148.00 174.00   0.50    0.22    --  105.75  57.00  30.00   52
 83  \w     97.00 123.00   0.50    0.22    --  105.75  57.00  30.00   52
 84  \w    149.00 175.00   0.50    0.22    --  105.75  77.00 120.00   52
 85  \w    103.00 173.00   0.50    0.22    --  105.75  57.00  90.00  140
 86  \w    122.00 147.00   0.50    0.22    --  105.75  77.00 120.00   50
 87  \w     98.00 155.00   0.50    0.22    --  105.75  57.00 120.00  114
 88  \w     93.00 128.00   0.50    0.22    --  105.75  57.00   0.00   70
 89  \w    138.00 168.00   0.50    0.22    --  105.75  57.00   0.00   60
 90  \w    143.00 172.00   0.50    0.22    --  105.75  38.00 -30.00   58
 91  \w    130.00 171.00   0.50    0.22    --  105.75  57.00 -60.00   82
 92  \w    100.00 125.00   0.50    0.22    --  105.75  57.00 -60.00   50
 93  \w    102.00 138.00   0.50    0.22    --  105.75  38.00 -30.00   72
 94  \w    140.00 175.00   0.50    0.22    --  105.75  38.00-180.00   70
 95  \w     99.00 127.00   0.50    0.22    --  105.75  38.00-150.00   56
 96  \w    108.00 133.00   0.50    0.22    --  105.75  38.00-180.00   50
 97  \w     36.00  67.00   0.50    0.22    --  105.75 -99.00 -90.00   62
 98  \w     37.00 108.00   0.50    0.22    --  105.75-125.00-150.00  142
 99  \w     36.00 106.00   0.50    0.22    --  105.75 -99.00-150.00  140
100  \w     74.00 105.00   0.50    0.22    --  105.75 -99.00 -90.00   62
101  \w     36.00  92.00   0.50    0.05    --   49.41-125.00 -60.00  112
102  \w     59.00 109.00   0.50    0.22    --  105.75-125.00   0.00  100
103  \w     41.00  67.00   0.50    0.22    --  105.75 -99.00  30.00   52
104  \w     66.00 106.00   0.50    0.22    --  105.75 -99.00   0.00   80
105  \w     71.00 106.00   0.50    0.22    --  105.75 -99.00  60.00   70
106  \w     48.00 105.00   0.50    0.22    --  105.75 -99.00 120.00  114
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0670029000
_diffrn_orient_matrix_UB_12      0.0309875000
_diffrn_orient_matrix_UB_13      0.0783031000
_diffrn_orient_matrix_UB_21      -0.1222474000
_diffrn_orient_matrix_UB_22      0.1519934000
_diffrn_orient_matrix_UB_23      -0.0028531000
_diffrn_orient_matrix_UB_31      -0.1157883000
_diffrn_orient_matrix_UB_32      -0.0801862000
_diffrn_orient_matrix_UB_33      0.0710672000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0456
_diffrn_reflns_av_unetI/netI     0.0403
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            28265
_diffrn_reflns_point_group_measured_fraction_full 0.949
_diffrn_reflns_point_group_measured_fraction_max 0.949
_diffrn_reflns_theta_full        66.575
_diffrn_reflns_theta_max         66.575
_diffrn_reflns_theta_min         3.034
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    9.523
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.663
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.64a (Rigaku Oxford Diffraction, 2022)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.449
_exptl_crystal_description       Plate
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.701
_refine_diff_density_min         -0.611
_refine_diff_density_rms         0.055
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   -0.021(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     585
_refine_ls_number_reflns         7799
_refine_ls_number_restraints     303
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0263
_refine_ls_R_factor_gt           0.0251
_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^)+(0.0290P)^2^+0.3133P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0605
_refine_ls_wR_factor_ref         0.0612
_reflns_Friedel_coverage         0.897
_reflns_Friedel_fraction_full    0.897
_reflns_Friedel_fraction_max     0.897
_reflns_number_gt                7468
_reflns_number_total             7799
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3dt01623d2.cif
_cod_data_source_block           5
_cod_database_code               7713253
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'Sb O2 C27 H31'
_chemical_oxdiff_usercomment     BLK0546
_shelx_estimated_absorpt_t_max   0.599
_shelx_estimated_absorpt_t_min   0.421
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 1.021(10)
 -0.021(10)
2. 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
3. Uiso/Uaniso restraints and constraints
C221 \\sim C22A \\sim C23A \\sim C25A \\sim C26A \\sim C22B \\sim C23B \\sim
C25B \\sim C26B \\sim C224 \\sim C227: within 2A with sigma of 0.02 and sigma
for terminal atoms of 0.04 within 2A
C121 \\sim C22C \\sim C23C \\sim C25C \\sim C26C \\sim C124 \\sim C127: within
2A with sigma of 0.02 and sigma for terminal atoms of 0.04 within 2A
4. Rigid body (RIGU) restrains
 C221, C22A, C23A, C25A, C26A, C22B, C23B, C25B, C26B, C224, C227
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
 C121, C22C, C23C, C25C, C26C, C124, C127
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
5. Others
 Sof(C22B)=Sof(H22B)=Sof(C23B)=Sof(H23D)=Sof(C25B)=Sof(H25D)=Sof(C26B)=
 Sof(H26D)=1-FVAR(1)
 Sof(C22A)=Sof(H22A)=Sof(C23A)=Sof(H23C)=Sof(C25A)=Sof(H25C)=Sof(C26A)=
 Sof(H26C)=FVAR(1)
6.a Ternary CH refined with riding coordinates:
 C11(H11), C12(H12), C21(H21), C22(H22)
6.b Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C14(H14A,H14B), C15(H15A,H15B), C16(H16A,H16B), C23(H23A,
 H23B), C24(H24A,H24B), C25(H25A,H25B), C26(H26A,H26B)
6.c Aromatic/amide H refined with riding coordinates:
 C112(H112), C113(H113), C115(H115), C116(H116), C22C(H22F), C23C(H23H),
 C25C(H25E), C26C(H26E), C132(H132), C133(H133), C135(H135), C136(H136),
 C212(H212), C213(H213), C215(H215), C216(H216), C22A(H22A), C23A(H23C),
 C25A(H25C), C26A(H26C), C22B(H22B), C23B(H23D), C25B(H25D), C26B(H26D),
 C232(H232), C233(H233), C235(H235), C236(H236)
6.d Idealised Me refined as rotating group:
 C117(H11A,H11B,H11C), C127(H12A,H12B,H12C), C137(H13C,H13D,H13E), C217(H21A,
 H21B,H21C), C227(H22C,H22D,H22E), C237(H23E,H23F,H23G)
;
_shelx_res_checksum              28590
_shelx_hkl_checksum              50464
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.583
_oxdiff_exptl_absorpt_empirical_full_min 0.693