Total synthesis of (±)-epi-stemodan-13α,17-diol.
Chen, Song; Chen, Ting; Liu, Guanggen; Wang, Xiao; Zhu, Guili; Liu, Yongjiang; Fu, Shaomin; Liu, Bo; Organic & biomolecular chemistry 17 (2019) 4711–4714; doi:10.1039/c9ob00661c

data_7156783
_publ_section_title
;
 Total synthesis of (+-)-epi-stemodan-13\a,17-diol.
;
_journal_issue                   19
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              4711
_journal_page_last               4714
_journal_paper_doi               10.1039/c9ob00661c
_journal_volume                  17
_journal_year                    2019
_chemical_formula_moiety         'C20 H34 O2'
_chemical_formula_sum            'C20 H34 O2'
_chemical_formula_weight         306.47
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2019-02-28
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-03-02 deposited with the CCDC.    2019-04-17 downloaded from the CCDC.
;
_cell_angle_alpha                115.886(9)
_cell_angle_beta                 99.779(6)
_cell_angle_gamma                99.493(6)
_cell_formula_units_Z            6
_cell_length_a                   9.1145(5)
_cell_length_b                   18.1803(17)
_cell_length_c                   18.6882(17)
_cell_measurement_reflns_used    4810
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.6010
_cell_measurement_theta_min      3.3870
_cell_volume                     2643.8(5)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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      293.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0874
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
  1 omega  -82.00   12.50   0.9000   22.5000
omega____ theta____ kappa____ phi______ frames
    -      -14.8106  -77.0000  150.0000 105

  2 omega  -42.00   51.60   0.9000   22.5000
omega____ theta____ kappa____ phi______ frames
    -      -14.8106   77.0000  -90.0000 104

  3 omega  -87.00  -60.90   0.9000   22.5000
omega____ theta____ kappa____ phi______ frames
    -      -14.8106 -178.0000  -60.0000 29

  4 omega  -12.00   22.20   0.9000   22.5000
omega____ theta____ kappa____ phi______ frames
    -      -14.8106  -99.0000   30.0000 38

  5 omega  -46.00  -17.20   0.9000   22.5000
omega____ theta____ kappa____ phi______ frames
    -       16.9200  -57.0000 -120.0000 32

  6 omega    0.00   83.70   0.9000   22.5000
omega____ theta____ kappa____ phi______ frames
    -       16.9200   38.0000   60.0000 93
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0079455000
_diffrn_orient_matrix_UB_12      -0.0005288000
_diffrn_orient_matrix_UB_13      0.0368896000
_diffrn_orient_matrix_UB_21      -0.0025219000
_diffrn_orient_matrix_UB_22      -0.0437271000
_diffrn_orient_matrix_UB_23      -0.0183312000
_diffrn_orient_matrix_UB_31      0.0815839000
_diffrn_orient_matrix_UB_32      0.0108073000
_diffrn_orient_matrix_UB_33      0.0150384000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0455
_diffrn_reflns_av_unetI/netI     0.0967
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            20338
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.371
_diffrn_reflns_theta_min         2.958
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.072
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.76385
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.155
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1020
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.461
_refine_diff_density_min         -0.481
_refine_diff_density_rms         0.090
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.284
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     619
_refine_ls_number_reflns         10807
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.284
_refine_ls_R_factor_all          0.1951
_refine_ls_R_factor_gt           0.1359
_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^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3946
_refine_ls_wR_factor_ref         0.4337
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5620
_reflns_number_total             10807
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9ob00661c2.cif
_cod_data_source_block           190227_s9_cs
_cod_depositor_comments          'Adding full bibliography for 7156783.cif.'
_cod_original_cell_volume        2643.8(4)
_cod_database_code               7156783
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         c12h12n2o3
_shelx_estimated_absorpt_t_max   0.982
_shelx_estimated_absorpt_t_min   0.975
_reflns_odcompleteness_completeness 99.82
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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. Restrained distances
 O3-H3
 1 with sigma of 0.02
3.a Ternary CH refined with riding coordinates:
 C2(H2A), C4(H4), C7(H7), C30(H30), C33(H33), C35(H35), C50(H50), C53(H53),
 C55(H55)
3.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C5(H5A,H5B), C6(H6A,H6B), C9(H9A,H9B), C10(H10A,H10B), C11(H11A,
 H11B), C14(H14A,H14B), C15(H15A,H15B), C16(H16A,H16B), C17(H17A,H17B),
 C22(H22A,H22B), C23(H23A,H23B), C26(H26A,H26B), C27(H27A,H27B), C28(H28A,H28B),
  C31(H31A,H31B), C32(H32A,H32B), C34(H34A,H34B), C36(H36A,H36B), C37(H37A,
 H37B), C42(H42A,H42B), C43(H43A,H43B), C46(H46A,H46B), C47(H47A,H47B),
 C48(H48A,H48B), C51(H51A,H51B), C52(H52A,H52B), C54(H54A,H54B), C56(H56A,H56B),
  C57(H57A,H57B)
3.c Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C19(H19A,H19B,H19C), C20(H20A,H20B,H20C), C38(H38A,H38B,
 H38C), C39(H39A,H39B,H39C), C40(H40A,H40B,H40C), C58(H58A,H58B,H58C), C59(H59A,
 H59B,H59C), C60(H60A,H60B,H60C)
3.d Idealised tetrahedral OH refined as rotating group:
 O2(H2), O4(H4A), O5(H5)
;
_shelx_res_checksum              10214
_olex2_submission_special_instructions 'No special instructions were received'