Synthesis of menarandroside A from dehydroepiandrosterone.
Offei, Samuel D.; Arman, Hadi D.; Yoshimoto, Francis K.; Organic & biomolecular chemistry 21 (2023) 3172–3176; doi:10.1039/d3ob00054k

data_7159216
_publ_section_title
;
 Synthesis of menarandroside A from dehydroepiandrosterone.
;
_journal_issue                   15
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              3172
_journal_page_last               3176
_journal_paper_doi               10.1039/d3ob00054k
_journal_volume                  21
_journal_year                    2023
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C20 H32 O3, H2 O'
_chemical_formula_sum            'C20 H34 O4'
_chemical_formula_weight         338.47
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2020-08-11
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2019.10.09 svn.r3662 for Rigaku Oxford Diffraction, GUI svn.r5959)
;
_audit_update_record
;
2020-11-20 deposited with the CCDC.	2023-03-01 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 129.016(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   29.0654(11)
_cell_length_b                   6.15840(10)
_cell_length_c                   13.8163(5)
_cell_measurement_reflns_used    9288
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.9270
_cell_measurement_theta_min      3.4630
_cell_volume                     1921.50(19)
_computing_cell_refinement       'CrysAlisPro 1.171.40.63a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.63a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.63a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-ac4 (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 0.999
_diffrn_measured_fraction_theta_max 0.964
_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     28.00 123.00   0.50    0.63    --   46.87  14.00 -29.00  190
  2  \w     88.00 178.00   0.50    2.53    --  106.69  14.00 -29.00  180
  3  \w     95.00 176.00   0.50    2.53    --  106.69  45.00 150.00  162
  4  \w     92.00 176.00   0.50    2.53    --  106.69  61.00  30.00  168
  5  \w     65.00 101.00   0.50    2.53    --  106.69 -77.00 -30.00   72
  6  \w     34.00  70.00   0.50    2.53    --  106.69 -61.00-120.00   72
  7  \w     34.00  68.00   0.50    2.53    --  106.69 -61.00-150.00   68
  8  \w     36.00  67.00   0.50    2.53    --  106.69 -94.00-150.00   62
  9  \w     34.00  67.00   0.50    2.53    --  106.69 -61.00 -30.00   66
 10  \w     36.00  65.00   0.50    2.53    --  106.69 -61.00   0.00   58
 11  \w     37.00  67.00   0.50    2.53    --  106.69 -61.00  60.00   60
 12  \w     38.00  70.00   0.50    2.53    --  106.69 -61.00  90.00   64
 13  \w     37.00 111.00   0.50    2.53    --  106.69-125.00  90.00  148
 14  \w     32.00 121.00   0.50    0.63    --   46.87  37.00 -30.00  178
 15  \w     33.00 119.00   0.50    0.63    --   46.87  47.00 157.62  172
 16  \w     32.00 120.00   0.50    0.63    --   46.87  52.00  50.40  176
 17  \w     32.00 120.00   0.50    0.63    --   46.87  50.00 120.11  176
 18  \w     32.00 120.00   0.50    0.63    --   46.87  51.00  75.85  176
 19  \w    -27.00  43.00   0.50    0.63    --   46.87 -37.00  60.00  140
 20  \w    -28.00  29.00   0.50    0.63    --   46.87 -14.00 159.00  114
 21  \w    -29.00  29.00   0.50    0.63    --  -46.87  14.00 -29.00  116
 22  \w    -51.00 -16.00   0.50    2.53    --  -88.50  45.00 -30.00   70
 23  \w    -71.00 -15.00   0.50    2.53    --  -88.50  61.00 120.00  112
 24  \w   -110.00 -75.00   0.50    2.53    --  -88.50 -49.00  32.74   70
 25  \w   -105.00 -79.00   0.50    2.53    --  -88.50 -56.00  75.75   52
 26  \w   -100.00 -74.00   0.50    2.53    --  -88.50 -45.00  90.00   52
 27  \w   -123.00 -29.00   0.50    0.63    --  -46.87 -14.00 159.00  188
 28  \w    -48.00 -16.00   0.50    2.53    --  -88.50  45.00-180.00   64
 29  \w   -100.00 -74.00   0.50    2.53    --  -88.50 -55.00 -31.84   52
 30  \w   -120.00 -32.00   0.50    0.63    --  -46.87 -50.00  31.20  176
 31  \w   -119.00 -73.00   0.50    2.53    --  -88.50 -54.00   0.96   92
 32  \w   -140.00-114.00   0.50    2.53    --  -88.50 -45.00  90.00   52
 33  \w   -164.00 -71.00   0.50    2.53    --  -88.50 -14.00 159.00  186
 34  \w   -160.00 -72.00   0.50    2.53    --  -88.50 -54.00  28.03  176
 35  \w   -160.00 -73.00   0.50    2.53    --  -88.50 -52.00 127.27  174
 36  \w   -156.00 -74.00   0.50    2.53    --  -88.50 -49.00 -17.87  164
 37  \w   -120.00 -83.00   0.50    0.63    --  -46.87 -57.00-180.00   74
 38  \w   -160.00 -73.00   0.50    2.53    --  -88.50 -55.00   9.29  174
 39  \w   -160.00 -72.00   0.50    2.53    --  -88.50 -54.00  52.06  176
 40  \w   -160.00 -78.00   0.50    2.53    --  -88.50 -56.00  71.10  164
 41  \w   -160.00 -72.00   0.50    2.53    --  -88.50 -51.00  26.76  176
 42  \w   -161.00 -73.00   0.50    2.53    --  -88.50 -44.00  78.92  176
 43  \w   -160.00 -72.00   0.50    2.53    --  -88.50 -51.00  13.74  176
 44  \w   -160.00 -73.00   0.50    2.53    --  -88.50 -50.00  79.94  174
 45  \w   -160.00 -78.00   0.50    2.53    --  -88.50 -56.00  64.21  164
 46  \w   -160.00 -74.00   0.50    2.53    --  -88.50 -48.00 104.08  172
;
_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      -0.0679810000
_diffrn_orient_matrix_UB_12      -0.0200686000
_diffrn_orient_matrix_UB_13      -0.0883962000
_diffrn_orient_matrix_UB_21      -0.0000201000
_diffrn_orient_matrix_UB_22      -0.0444315000
_diffrn_orient_matrix_UB_23      -0.1097952000
_diffrn_orient_matrix_UB_31      0.0056616000
_diffrn_orient_matrix_UB_32      -0.2452981000
_diffrn_orient_matrix_UB_33      0.0271968000
_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  0.0233
_diffrn_reflns_av_unetI/netI     0.0160
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.964
_diffrn_reflns_limit_h_max       36
_diffrn_reflns_limit_h_min       -35
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            20437
_diffrn_reflns_point_group_measured_fraction_full 0.957
_diffrn_reflns_point_group_measured_fraction_max 0.895
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.815
_diffrn_reflns_theta_min         3.461
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.632
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.822
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.63a (Rigaku Oxford Diffraction, 2019)
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            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.170
_exptl_crystal_description       plate
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.137
_exptl_crystal_size_mid          0.074
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.130
_refine_diff_density_min         -0.139
_refine_diff_density_rms         0.028
_refine_ls_abs_structure_details
;
 Flack x determined using 1302 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.12(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     234
_refine_ls_number_reflns         3630
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.0408
_refine_ls_R_factor_gt           0.0380
_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^)+(0.0450P)^2^+0.7500P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0973
_refine_ls_wR_factor_ref         0.0993
_reflns_Friedel_coverage         0.692
_reflns_Friedel_fraction_full    0.906
_reflns_Friedel_fraction_max     0.811
_reflns_number_gt                3345
_reflns_number_total             3630
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ob00054k2.cif
_cod_data_source_block           hpd197
_cod_depositor_comments
'Adding full bibliography for 7159215--7159218.cif.'
_cod_original_cell_volume        1921.50(16)
_cod_database_code               7159216
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H O'
_chemical_oxdiff_usercomment     63ag
_shelx_estimated_absorpt_t_max   0.981
_shelx_estimated_absorpt_t_min   0.918
_reflns_odcompleteness_completeness 100.00
_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 C(H,H,H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C5(H5), C12(H12), C7(H7), C13(H13), C1(H1A), C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C6(H6A,H6B), C2(H2A,H2B), C14(H14A,H14B), C17(H17A,H17B),
 C10(H10A,H10B), C11(H11A,H11B), C20(H20A,H20B)
2.c Aromatic/amide H refined with riding coordinates:
 C15(H15)
2.d Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C19(H19A,H19B,H19C)
;
_shelx_res_checksum              58203
_olex2_exptl_crystal_mounting_method 'nylon loop'
_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 1.327
_oxdiff_exptl_absorpt_empirical_full_min 0.863