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_7713249
_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_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           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-12-13
_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                63.873(5)
_cell_angle_beta                 84.156(4)
_cell_angle_gamma                65.488(4)
_cell_formula_units_Z            2
_cell_length_a                   10.0944(4)
_cell_length_b                   11.6974(5)
_cell_length_c                   12.2709(6)
_cell_measurement_reflns_used    16139
_cell_measurement_temperature    101(2)
_cell_measurement_theta_max      72.7410
_cell_measurement_theta_min      4.0010
_cell_volume                     1177.82(11)
_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      101(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_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   -112.00 -83.00   0.50    0.34    --  -49.41-157.00 -56.00   58
  2  \w    -92.00 -67.00   0.50    0.34    --  -49.41 157.00 -21.00   50
  3  \w    -49.00 -11.00   0.50    0.34    --  -49.41 120.00-177.00   76
  4  \w     33.00  87.00   0.50    0.34    --   49.41-120.00  98.00  108
  5  \w     86.00 118.00   0.50    0.34    --   49.41 157.00 -21.00   64
  6  \w     77.00 102.00   0.50    0.34    --   49.41-157.00 -56.00   50
  7  \w    -84.00 -18.00   0.50    1.34    --  -84.25 120.00-177.00  132
  8  \w   -139.00-114.00   0.50    1.34    --  -84.25-120.00  98.00   50
  9  \w   -102.00 -76.00   0.50    1.34    --  -84.25-157.00 -56.00   52
 10  \w    106.00 132.00   0.50    1.34    --  105.75-157.00 -56.00   52
 11  \w     75.00 131.00   0.50    1.34    --  105.75 157.00 -21.00  112
 12  \w    103.00 175.00   0.50    1.34    --  105.75 120.00-177.00  144
 13  \w     83.00 108.00   0.50    1.34    --  105.75-120.00  98.00   50
 14  \w     -7.00  18.00   0.50    0.34    --   16.00  82.00-122.25   50
 15  \w     -8.00  17.00   0.50    0.34    --   16.00  84.00 116.41   50
 16  \w      2.00  28.00   0.50    0.34    --   20.00  72.00  16.98   52
 17  \w    -37.00 -12.00   0.50    0.34    --  -28.00 -67.00 156.72   50
 18  \w    -39.00 -14.00   0.50    0.34    --  -28.00 -66.00  88.70   50
 19  \w     19.00  45.00   0.50    0.34    --   32.00  60.00-171.49   52
 20  \w     20.00  49.00   0.50    0.34    --   32.00  60.00 -73.92   58
 21  \w     22.00  47.00   0.50    0.34    --   36.00  61.00  36.00   50
 22  \w     23.00  53.00   0.50    0.34    --   36.00  59.00  97.95   60
 23  \w     22.00  47.00   0.50    0.34    --   36.00  60.00  -1.80   50
 24  \w    -53.00 -28.00   0.50    0.34    --  -40.00 -59.00-110.14   50
 25  \w     27.00  53.00   0.50    0.34    --   40.00  59.00 -50.81   52
 26  \w     27.00  52.00   0.50    0.34    --   40.00  59.00 139.14   50
 27  \w    -66.00 -37.00   0.50    0.34    --  -48.00 -53.00 159.75   58
 28  \w     42.00  73.00   0.50    0.34    --   49.41  56.00-139.60   62
 29  \w     96.00 121.00   0.50    0.34    --   49.41  56.00-139.60   50
 30  \w   -114.00 -89.00   0.50    0.34    --  -56.00 -52.00  90.72   50
 31  \w    -70.00 -44.00   0.50    0.34    --  -56.00 -54.00-161.52   52
 32  \w    -70.00 -45.00   0.50    0.34    --  -56.00 -52.00  90.72   50
 33  \w    -77.00 -44.00   0.50    0.34    --  -56.00 -56.00 -31.12   66
 34  \w   -113.00 -87.00   0.50    0.34    --  -56.00 -54.00-161.52   52
 35  \w   -105.00 -47.00   0.50    0.34    --  -60.00 -56.00 -84.83  116
 36  \w   -130.00-101.00   0.50    0.34    --  -60.00 -53.00  68.76   58
 37  \w    -74.00 -48.00   0.50    0.34    --  -60.00 -53.00  -6.27   52
 38  \w    -77.00 -48.00   0.50    0.34    --  -60.00 -53.00  68.76   58
 39  \w     48.00  73.00   0.50    0.34    --   60.00  55.00 110.75   50
 40  \w     48.00  74.00   0.50    0.34    --   60.00  54.00 -50.17   52
 41  \w    -80.00 -55.00   0.50    0.34    --  -64.00 -50.00  10.55   50
 42  \w    -81.00 -56.00   0.50    1.34    --  -68.00 -54.00 177.78   50
 43  \w     57.00  82.00   0.50    0.34    --   68.00  55.00 142.60   50
 44  \w    -86.00 -60.00   0.50    1.34    --  -72.00 -54.00 144.90   52
 45  \w    -86.00 -60.00   0.50    1.34    --  -72.00 -54.00 133.00   52
 46  \w    -92.00 -64.00   0.50    1.34    --  -76.00 -56.00-116.65   56
 47  \w    -92.00 -66.00   0.50    1.34    --  -76.00 -49.00 -54.20   52
 48  \w    -89.00 -63.00   0.50    1.34    --  -76.00 -56.00  48.11   52
 49  \w    -95.00 -69.00   0.50    1.34    --  -80.00 -55.00 116.23   52
 50  \w   -106.00 -73.00   0.50    1.34    --  -84.25 -51.00 -72.41   66
 51  \w    -97.00 -72.00   0.50    1.34    --  -84.25 -55.00 -76.77   50
 52  \w   -118.00 -74.00   0.50    1.34    --  -84.25 -51.00-147.83   88
 53  \w    -99.00 -72.00   0.50    1.34    --  -84.25 -55.00 -14.52   54
 54  \w   -153.00-112.00   0.50    1.34    --  -84.25 -55.00 -14.52   82
 55  \w   -146.00-121.00   0.50    1.34    --  -84.25 -51.00-147.83   50
 56  \w   -105.00 -73.00   0.50    1.34    --  -84.25 -53.00 100.33   64
 57  \w   -155.00-115.00   0.50    1.34    --  -84.25 -53.00 -52.25   80
 58  \w   -137.00-111.00   0.50    1.34    --  -84.25 -51.00 -72.41   52
 59  \w   -108.00 -72.00   0.50    1.34    --  -84.25 -54.00 126.30   72
 60  \w   -100.00 -72.00   0.50    1.34    --  -84.25 -54.00   8.90   56
 61  \w   -156.00-128.00   0.50    1.34    --  -84.25 -54.00 126.30   56
 62  \w   -125.00 -72.00   0.50    1.34    --  -84.25 -55.00-121.80  106
 63  \w   -153.00-122.00   0.50    1.34    --  -84.25 -52.00  21.43   62
 64  \w   -101.00 -76.00   0.50    1.34    --  -84.25 -56.00 142.56   50
 65  \w   -141.00-115.00   0.50    1.34    --  -84.25 -56.00 142.56   52
 66  \w    -98.00 -73.00   0.50    1.34    --  -84.25 -53.00 -52.25   50
 67  \w    -98.00 -73.00   0.50    1.34    --  -84.25 -52.00  21.43   50
 68  \w    -99.00 -73.00   0.50    1.34    --  -84.25 -50.00-176.44   52
 69  \w    -99.00 -73.00   0.50    1.34    --  -84.25 -52.00  78.05   52
 70  \w   -102.00 -72.00   0.50    1.34    --  -84.25 -55.00 150.01   60
 71  \w   -133.00-107.00   0.50    1.34    --  -84.25 -55.00 -76.77   52
 72  \w    -99.00 -72.00   0.50    1.34    --  -84.25 -55.00  45.42   54
 73  \w   -102.00 -76.00   0.50    1.34    --  -84.25 -56.00   4.48   52
 74  \w   -138.00-112.00   0.50    1.34    --  -84.25 -56.00   4.48   52
 75  \w    -62.00 -27.00   0.50    1.34    --  -84.25  57.00  60.00   70
 76  \w   -103.00 -77.00   0.50    1.34    --  -84.25 -56.00 -24.43   52
 77  \w   -100.00 -75.00   0.50    1.34    --  -84.25 -52.00 -91.49   50
 78  \w   -106.00 -72.00   0.50    1.34    --  -84.25 -55.00 174.37   68
 79  \w   -155.00-118.00   0.50    1.34    --  -84.25 -55.00 174.37   74
 80  \w   -102.00 -74.00   0.50    1.34    --  -84.25 -54.00  70.22   56
 81  \w     93.00 166.00   0.50    1.34    --  105.75  57.00 -30.00  146
 82  \w     79.00 104.00   0.50    1.34    --  105.75 -99.00 150.00   50
 83  \w     43.00  69.00   0.50    1.34    --  105.75 -99.00 150.00   52
 84  \w     77.00 106.00   0.50    1.34    --  105.75-125.00 -60.00   58
 85  \w     48.00  73.00   0.50    1.34    --  105.75-125.00 -60.00   50
 86  \w    101.00 153.00   0.50    1.34    --  105.75  57.00   0.00  104
 87  \w     34.00  63.00   0.50    1.34    --  105.75 -57.00   0.00   58
 88  \w     37.00  64.00   0.50    1.34    --  105.75 -57.00 -60.00   54
 89  \w    146.00 172.00   0.50    1.34    --  105.75  19.00 120.00   52
 90  \w     98.00 136.00   0.50    1.34    --  105.75  19.00 120.00   76
 91  \w     77.00 106.00   0.50    1.34    --  105.75 -99.00 -60.00   58
 92  \w     35.00  66.00   0.50    1.34    --  105.75 -57.00  90.00   62
 93  \w     77.00 106.00   0.50    1.34    --  105.75 -99.00  90.00   58
 94  \w     39.00  72.00   0.50    1.34    --  105.75 -99.00  90.00   66
 95  \w     38.00  74.00   0.50    1.34    --  105.75 -99.00 -60.00   72
 96  \w     98.00 163.00   0.50    1.34    --  105.75  38.00 150.00  130
 97  \w     98.00 177.00   0.50    1.34    --  105.75  38.00 -90.00  158
 98  \w     35.00  66.00   0.50    1.34    --  105.75 -57.00 -30.00   62
 99  \w    111.00 136.00   0.50    1.34    --  105.75  77.00   0.00   50
100  \w     36.00  62.00   0.50    1.34    --  105.75 -57.00-180.00   52
101  \w     37.00  67.00   0.50    1.34    --  105.75 -57.00  60.00   60
102  \w     58.00 100.00   0.50    1.34    --  105.75-125.00  30.00   84
103  \w     41.00  67.00   0.50    1.34    --  105.75 -57.00 -90.00   52
104  \w    135.00 165.00   0.50    1.34    --  105.75  57.00  60.00   60
105  \w     41.00  67.00   0.50    1.34    --  105.75 -57.00 150.00   52
106  \w     95.00 129.00   0.50    1.34    --  105.75  57.00  60.00   68
107  \w    127.00 169.00   0.50    1.34    --  105.75  38.00-180.00   84
108  \w     34.00  67.00   0.50    1.34    --  105.75 -57.00 120.00   66
;
_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      0.0272028000
_diffrn_orient_matrix_UB_12      -0.1426189000
_diffrn_orient_matrix_UB_13      0.1087632000
_diffrn_orient_matrix_UB_21      0.0380830000
_diffrn_orient_matrix_UB_22      -0.0691288000
_diffrn_orient_matrix_UB_23      -0.0873877000
_diffrn_orient_matrix_UB_31      0.1619334000
_diffrn_orient_matrix_UB_32      -0.0292940000
_diffrn_orient_matrix_UB_33      0.0167634000
_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  0.0663
_diffrn_reflns_av_unetI/netI     0.0371
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            27689
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.070
_diffrn_reflns_theta_max         67.070
_diffrn_reflns_theta_min         4.032
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    9.434
_exptl_absorpt_correction_T_max  0.781
_exptl_absorpt_correction_T_min  0.533
_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    1.436
_exptl_crystal_description       Plate
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.04
_refine_diff_density_max         1.012
_refine_diff_density_min         -1.713
_refine_diff_density_rms         0.095
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     338
_refine_ls_number_reflns         4184
_refine_ls_number_restraints     285
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0438
_refine_ls_R_factor_gt           0.0392
_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^)+(0.0417P)^2^+2.4993P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0939
_refine_ls_wR_factor_ref         0.0961
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3794
_reflns_number_total             4184
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3dt01623d2.cif
_cod_data_source_block           3
_cod_database_code               7713249
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'Sb O2 C27 H31'
_chemical_oxdiff_usercomment     BLK0529
_shelx_estimated_absorpt_t_max   0.704
_shelx_estimated_absorpt_t_min   0.423
_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
2. Uiso/Uaniso restraints and constraints
O1A \\sim C1A \\sim C2A \\sim C3A \\sim C4A \\sim C5A \\sim C6A \\sim O1B \\sim
C1B \\sim C2B \\sim C3B \\sim C4B \\sim C5B \\sim C6B: within 2A with sigma of
0.04 and sigma for terminal atoms of 0.08 within 2A
3. Rigid body (RIGU) restrains
 O1A, C1A, C2A, C3A, C4A, C5A, C6A, O1B, C1B, C2B, C3B, C4B, C5B, C6B
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4. Same fragment restrains
{O1A, C1A, C2A, C3A, C4A, C5A, C6A} sigma for 1-2: 0.02, 1-3: 0.04
as in
{O1B, C1B, C2B, C3B, C4B, C5B, C6B}
5. Others
 Sof(O1B)=Sof(C1B)=Sof(H1B)=Sof(C2B)=Sof(H2B)=Sof(C3B)=Sof(H3BA)=Sof(H3BB)=
 Sof(C4B)=Sof(H4BA)=Sof(H4BB)=Sof(C5B)=Sof(H5BA)=Sof(H5BB)=Sof(C6B)=Sof(H6BA)=
 Sof(H6BB)=1-FVAR(1)
 Sof(O1A)=Sof(C1A)=Sof(H1A)=Sof(C2A)=Sof(H2A)=Sof(C3A)=Sof(H3AA)=Sof(H3AB)=
 Sof(C4A)=Sof(H4AA)=Sof(H4AB)=Sof(C5A)=Sof(H5AA)=Sof(H5AB)=Sof(C6A)=Sof(H6AA)=
 Sof(H6AB)=FVAR(1)
6.a Ternary CH refined with riding coordinates:
 C1A(H1A), C2A(H2A), C1B(H1B), C2B(H2B)
6.b Secondary CH2 refined with riding coordinates:
 C3A(H3AA,H3AB), C4A(H4AA,H4AB), C5A(H5AA,H5AB), C6A(H6AA,H6AB), C3B(H3BA,
 H3BB), C4B(H4BA,H4BB), C5B(H5BA,H5BB), C6B(H6BA,H6BB)
6.c Aromatic/amide H refined with riding coordinates:
 C12(H12), C13(H13), C15(H15), C16(H16), C22(H22), C23(H23), C25(H25),
 C26(H26), C32(H32), C33(H33), C35(H35), C36(H36)
6.d Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C27(H27A,H27B,H27C), C37(H37A,H37B,H37C)
;
_shelx_res_checksum              856
_shelx_hkl_checksum              1223
_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 1.679
_oxdiff_exptl_absorpt_empirical_full_min 0.512