The crystal structure of (5R,8R,9R,10R,12R,13R,14R)-12-hydroxy-4,4,8,10,14-pentamethyl-17-((R)-2,6,6-trimethyltetrahydro-2H-pyran-2-yl)tetradecahydro-3H-cyclopenta[a]phenanthrene-3,6(2H)-dione, C30H48O4
Sun, Ke-wei; Wang, Hui-yun; Ma, Guang-qun; Luo, Qin; Wang, Yun-Hui; Meng, Qing-Guo; Zeitschrift für Kristallographie - New Crystal Structures 236 (2021) 17–20; doi:10.1515/ncrs-2020-0459

data_8104870
_publ_section_title
;
 The crystal structure of
 (5R,8R,9R,10R,12R,13R,14R)-12-hydroxy-4,4,8,10,14-pentamethyl-17-((R)-2,6,6-trimethyltetrahydro-2H-pyran-2-yl)tetradecahydro-3H-cyclopenta[a]phenanthrene-3,6(2H)-dione,
 C30H48O4
;
_journal_issue                   1
_journal_name_full
'Zeitschrift f\"ur Kristallographie - New Crystal Structures'
_journal_page_first              17
_journal_page_last               20
_journal_paper_doi               10.1515/ncrs-2020-0459
_journal_volume                  236
_journal_year                    2021
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C30 H48 O4'
_chemical_formula_sum            'C30 H48 O4'
_chemical_formula_weight         472.68
_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
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   12.34133(14)
_cell_length_b                   16.50759(15)
_cell_length_c                   26.8804(2)
_cell_measurement_reflns_used    31279
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      66.5970
_cell_measurement_theta_min      3.9080
_cell_volume                     5476.23(9)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_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 0.982
_diffrn_measured_fraction_theta_max 0.864
_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    -87.00 -61.00   1.00    3.00    --  -41.67 125.00-150.00   26
  2  \w    -14.00  65.00   1.00    3.00    --   41.67 -38.00-150.00   79
  3  \w     14.00 117.00   1.00    3.00    --   41.67  77.00 150.00  103
  4  \w    -29.00  56.00   1.00    3.00    --   41.67 -57.00  30.00   85
  5  \w     21.00  47.00   1.00   16.00    --   92.50-125.00  30.00   26
  6  \w     59.00  93.00   1.00   16.00    --   92.50-125.00  30.00   34
  7  \w     82.00 119.00   1.00   16.00    --   92.50 -15.00 150.00   37
  8  \w     22.00  92.00   1.00   16.00    --   92.50-125.00-180.00   70
  9  \w     55.00  81.00   1.00   16.00    --   92.50 -95.00-180.00   26
 10  \w     39.00  73.00   1.00   16.00    --   92.50 -95.00 -30.00   34
 11  \w     26.00  52.00   1.00   16.00    --   92.50 -30.00-120.00   26
 12  \w     45.00  71.00   1.00   16.00    --   92.50 -95.00-150.00   26
 13  \w     74.00 119.00   1.00   16.00    --   92.50  30.00 120.00   45
 14  \w    129.00 155.00   1.00   16.00    --   92.50  30.00 120.00   26
 15  \w     61.00 158.00   1.00   16.00    --   92.50  77.00  90.00   97
 16  \w    133.00 168.00   1.00   16.00    --   92.50  30.00 -30.00   35
 17  \w     20.00  45.00   1.00   16.00    --   92.50 -45.00 -60.00   25
 18  \w     27.00  63.00   1.00   16.00    --   92.50 -61.00-180.00   36
 19  \w     80.00 122.00   1.00   16.00    --   92.50 -61.00-180.00   42
 20  \w     60.00 107.00   1.00   16.00    --   92.50  77.00 -60.00   47
 21  \w     64.00 166.00   1.00   16.00    --   92.50  30.00  60.00  102
 22  \w     19.00 103.00   1.00   16.00    --   92.50 -45.00-180.00   84
 23  \w     62.00 100.00   1.00   16.00    --   92.50 150.00-138.00   38
 24  \w     86.00 120.00   1.00   16.00    --   92.50 -30.00-120.00   34
 25  \w     74.00 100.00   1.00   16.00    --   92.50  77.00 -90.00   26
 26  \w     77.00 112.00   1.00   16.00    --   92.50 125.00 -90.00   35
 27  \w    117.00 152.00   1.00   16.00    --   92.50 125.00 -90.00   35
 28  \w    100.00 131.00   1.00   16.00    --   92.50 125.00  30.00   31
 29  \w    104.00 144.00   1.00   16.00    --   92.50  30.00  90.00   40
 30  \w     21.00  65.00   1.00   16.00    --   92.50 -15.00 -90.00   44
 31  \w    132.00 167.00   1.00   16.00    --   92.50  30.00  30.00   35
 32  \w     73.00 121.00   1.00   16.00    --   92.50  61.00 -90.00   48
 33  \w     92.00 142.00   1.00   16.00    --   92.50 -15.00 -90.00   50
 34  \w     60.00  90.00   1.00   16.00    --   92.50 -45.00 -60.00   30
 35  \w     82.00 108.00   1.00   16.00    --   92.50  30.00  30.00   26
 36  \w    116.00 157.00   1.00   16.00    --   92.50 125.00   0.00   41
 37  \w     95.00 120.00   1.00   16.00    --   92.50  30.00 -30.00   25
 38  \w     55.00  96.00   1.00   16.00    --   92.50 -61.00 -60.00   41
 39  \w     65.00 168.00   1.00   16.00    --   92.50  30.00-180.00  103
 40  \w     60.00  85.00   1.00   16.00    --   92.50 -95.00 150.00   25
 41  \w     67.00 115.00   1.00   16.00    --   92.50 -77.00  60.00   48
 42  \w     90.00 115.00   1.00   16.00    --   92.50  15.00-180.00   25
 43  \w     34.00  60.00   1.00   16.00    --   92.50-125.00-150.00   26
 44  \w     67.00  92.00   1.00   16.00    --   92.50-125.00 -60.00   25
 45  \w     41.00  66.00   1.00   16.00    --   92.50-125.00 120.00   25
 46  \w    127.00 158.00   1.00   16.00    --   92.50 125.00-120.00   31
 47  \w     12.00  37.00   1.00   16.00    --   92.50 -95.00-180.00   25
 48  \w     86.00 112.00   1.00   16.00    --   92.50  45.00-180.00   26
 49  \w     70.00  95.00   1.00   16.00    --   92.50 -45.00  30.00   25
 50  \w     86.00 111.00   1.00   16.00    --   92.50  61.00  90.00   25
 51  \w     60.00  86.00   1.00   16.00    --   92.50 -30.00-180.00   26
 52  \w     92.00 117.00   1.00   16.00    --   92.50  15.00 120.00   25
 53  \w     36.00  61.00   1.00   16.00    --   92.50 -15.00 150.00   25
;
_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      0.0273710000
_diffrn_orient_matrix_UB_12      0.0219452000
_diffrn_orient_matrix_UB_13      0.0542586000
_diffrn_orient_matrix_UB_21      -0.0586194000
_diffrn_orient_matrix_UB_22      -0.0770238000
_diffrn_orient_matrix_UB_23      0.0179807000
_diffrn_orient_matrix_UB_31      0.1067773000
_diffrn_orient_matrix_UB_32      -0.0479040000
_diffrn_orient_matrix_UB_33      -0.0040350000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0718
_diffrn_reflns_av_unetI/netI     0.0269
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.864
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            74600
_diffrn_reflns_point_group_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.851
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.778
_diffrn_reflns_theta_min         3.941
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance Ultra (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.576
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.34816
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
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    1.147
_exptl_crystal_description       block
_exptl_crystal_F_000             2080
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.192
_refine_diff_density_min         -0.173
_refine_diff_density_rms         0.050
_refine_ls_abs_structure_details
;
 Flack x determined using 3528 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.01(5)
_refine_ls_extinction_coef       0.00127(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     632
_refine_ls_number_reflns         9829
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0507
_refine_ls_R_factor_gt           0.0422
_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^)+(0.0478P)^2^+0.5838P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0899
_refine_ls_wR_factor_ref         0.0990
_reflns_Friedel_coverage         0.786
_reflns_Friedel_fraction_full    0.975
_reflns_Friedel_fraction_max     0.835
_reflns_number_gt                8694
_reflns_number_total             9829
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            suppl_j_ncrs-2020-0459_suppl.cif
_cod_data_source_block           1
_cod_database_code               8104870
_chemical_oxdiff_formula         'C1 H1 O1'
_shelx_estimated_absorpt_t_max   0.889
_shelx_estimated_absorpt_t_min   0.851
_reflns_odcompleteness_completeness 99.07
_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), C5'(H5'), C9(H9), C9'(H9'), C12(H12), C12'(H12'), C13(H13),
 C13'(H13'), C17(H17), C17'(H17')
2.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C1'(H1'A,H1'B), C2(H2A,H2B), C2'(H2'A,H2'B), C7(H7A,H7B),
 C7'(H7'A,H7'B), C11(H11A,H11B), C11'(H11C,H11D), C15(H15A,H15B), C15'(H15C,
 H15D), C16(H16A,H16B), C16'(H16C,H16D), C22(H22A,H22B), C22'(H22C,H22D),
 C23(H23A,H23B), C23'(H23C,H23D), C24(H24A,H24B), C24'(H24C,H24D)
2.c Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C18'(H18D,H18E,H18F), C19(H19A,H19B,H19C), C19'(H19D,
 H19E,H19F), C21(H21A,H21B,H21C), C21'(H21D,H21E,H21F), C26(H26A,H26B,H26C),
 C26'(H26D,H26E,H26F), C27(H27A,H27B,H27C), C27'(H27D,H27E,H27F), C28(H28A,H28B,
 H28C), C28'(H28D,H28E,H28F), C29(H29A,H29B,H29C), C29'(H29D,H29E,H29F),
 C30(H30A,H30B,H30C), C30'(H30D,H30E,H30F)
2.d Idealised tetrahedral OH refined as rotating group:
 O3(H3), O3'(H3')
;