Alismanin A, a Triterpenoid with a C34 Skeleton from Alisma orientale as a Natural Agonist of Human Pregnane X Receptor.
Wang, Chao; Huo, Xiao-Kui; Luan, Zhi-Lin; Cao, Fei; Tian, Xiang-Ge; Zhao, Xin-Yu; Sun, Cheng-Peng; Feng, Lei; Ning, Jing; Zhang, Bao-Jing; Ma, Xiao-Chi; Organic letters 19 (2017) 5645–5648; doi:10.1021/acs.orglett.7b02738

data_1547664
_publ_section_title
;
 Alismanin A, a Triterpenoid with a C34 Skeleton from Alisma orientale as
 a Natural Agonist of Human Pregnane X Receptor.
;
_journal_issue                   20
_journal_name_full               'Organic letters'
_journal_page_first              5645
_journal_page_last               5648
_journal_paper_doi               10.1021/acs.orglett.7b02738
_journal_volume                  19
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C29 H48 O3'
_chemical_formula_sum            'C29 H48 O3'
_chemical_formula_weight         444.67
_space_group_crystal_system      orthorhombic
_space_group_IT_number           18
_space_group_name_Hall           'P 2 2ab'
_space_group_name_H-M_alt        'P 21 21 2'
_symmetry_space_group_name_Hall  'P 2 2ab'
_symmetry_space_group_name_H-M   'P 21 21 2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2017-10-02
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   13.7185(2)
_cell_length_b                   20.7124(3)
_cell_length_c                   20.7597(3)
_cell_measurement_reflns_used    16222
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.4870
_cell_measurement_theta_min      4.2550
_cell_volume                     5898.72(15)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_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    'SIR2004 (Burla et al., 2007)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.991
_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     24.00 108.00   1.00    1.00    --   40.98  37.00 -60.00   84
  2  \w     97.00 124.00   1.00    2.41    --  106.95  45.00 -90.00   27
  3  \w    151.00 178.00   1.00    2.41    --  106.95  45.00 -90.00   27
  4  \w    153.00 178.00   1.00    2.41    --  106.95 125.00 -60.00   25
  5  \w     92.00 176.00   1.00    2.41    --  106.95  45.00  90.00   84
  6  \w     75.00 109.00   1.00    2.41    --  106.95 -94.00 120.00   34
  7  \w     77.00 120.00   1.00    2.41    --  106.95-125.00  90.00   43
  8  \w     36.00 135.00   1.00    2.41    --  106.95 -61.00  30.00   99
  9  \w     76.00 112.00   1.00    2.41    --  106.95-116.00 -89.00   36
 10  \w     39.00 134.00   1.00    2.41    --  106.95 -77.00 -90.00   95
 11  \w     36.00 130.00   1.00    2.41    --  106.95 -30.00 -90.00   94
 12  \w     34.00 144.00   1.00    2.41    --  106.95 -15.00  90.00  110
 13  \w     37.00 123.00   1.00    2.41    --  106.95 -61.00 150.00   86
 14  \w     38.00  64.00   1.00    2.41    --  106.95 -94.00 120.00   26
 15  \w    -33.00  14.00   1.00    1.00    --   40.98 -37.00 120.00   47
 16  \w    -95.00  -6.00   1.00    1.00    --  -40.98 125.00 -60.00   89
 17  \w    -74.00  18.00   1.00    1.00    --  -40.98  77.00-180.00   92
 18  \w   -109.00 -13.00   1.00    1.00    --  -40.98 -57.00  30.00   96
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0232262000
_diffrn_orient_matrix_UB_12      0.0510948000
_diffrn_orient_matrix_UB_13      0.0517520000
_diffrn_orient_matrix_UB_21      0.0453577000
_diffrn_orient_matrix_UB_22      0.0438124000
_diffrn_orient_matrix_UB_23      -0.0519478000
_diffrn_orient_matrix_UB_31      -0.0999892000
_diffrn_orient_matrix_UB_32      0.0317050000
_diffrn_orient_matrix_UB_33      -0.0115726000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0382
_diffrn_reflns_av_unetI/netI     0.0315
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            41680
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.739
_diffrn_reflns_theta_min         3.862
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.482
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83094
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.001
_exptl_crystal_description       block
_exptl_crystal_F_000             1968
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.530
_refine_diff_density_min         -0.367
_refine_diff_density_rms         0.071
_refine_ls_abs_structure_details
;
 Flack x determined using 4010 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.06(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     877
_refine_ls_number_reflns         11732
_refine_ls_number_restraints     567
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.1013
_refine_ls_R_factor_gt           0.0966
_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^)+(0.1170P)^2^+9.3562P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2569
_refine_ls_wR_factor_ref         0.2612
_reflns_Friedel_coverage         0.805
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.974
_reflns_number_gt                10743
_reflns_number_total             11732
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol7b02738_si_002.cif
_cod_data_source_block           exp_425
_cod_depositor_comments          'Adding full bibliography for 1547664.cif.'
_cod_original_cell_volume        5898.73(15)
_cod_database_code               1547664
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.944
_shelx_estimated_absorpt_t_min   0.910
_reflns_odcompleteness_completeness 99.91
_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. Restrained distances
 H3-H3_$1
 2.2 with sigma of 0.02
 H6_$1-H6
 2.2 with sigma of 0.02
 H13D-H52B
 2.2 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms restrained to be isotropic: with sigma of 0.01 and sigma
for terminal atoms of 0.02
Uanis(C13A) \\sim Ueq, Uanis(C34) \\sim Ueq, Uanis(C10) \\sim Ueq: with sigma
of 0.001 and sigma for terminal atoms of 0.002
Uanis(C32) \\sim Ueq: with sigma of 0.001 and sigma for terminal atoms of 0.002
Uanis(C25A) \\sim Ueq: with sigma of 0.001 and sigma for terminal atoms of 0.002
Uanis(C3A) \\sim Ueq: with sigma of 0.001 and sigma for terminal atoms of 0.002
4. Others
 Sof(O4A)=Sof(C30A)=Sof(C31A)=Sof(C32A)=Sof(H32A)=Sof(C33A)=Sof(C34A)=
 Sof(H34A)=Sof(H35A)=Sof(C39A)=Sof(C40A)=Sof(H40C)=Sof(H40D)=Sof(C41A)=
 Sof(H41C)=Sof(H41D)=Sof(C42A)=Sof(H42D)=Sof(H42E)=Sof(H42F)=Sof(C54A)=
 Sof(H54C)=Sof(H54D)=Sof(C55A)=Sof(H55C)=Sof(H55D)=Sof(C56A)=Sof(H56D)=
 Sof(H56E)=Sof(H56F)=Sof(C57A)=Sof(H57D)=Sof(H57E)=Sof(H57F)=Sof(C58A)=
 Sof(H58D)=Sof(H58E)=Sof(H58F)=1-FVAR(1)
 Sof(O4)=Sof(C30)=Sof(C31)=Sof(C32)=Sof(H32)=Sof(C33)=Sof(C34)=Sof(H34)=
 Sof(H35)=Sof(C39)=Sof(C40)=Sof(H40A)=Sof(H40B)=Sof(C41)=Sof(H41A)=Sof(H41B)=
 Sof(C42)=Sof(H42A)=Sof(H42B)=Sof(H42C)=Sof(C54)=Sof(H54A)=Sof(H54B)=Sof(C55)=
 Sof(H55A)=Sof(H55B)=Sof(C56)=Sof(H56A)=Sof(H56B)=Sof(H56C)=Sof(C57)=Sof(H57A)=
 Sof(H57B)=Sof(H57C)=Sof(C58)=Sof(H58A)=Sof(H58B)=Sof(H58C)=FVAR(1)
 Sof(O1A)=Sof(C1A)=Sof(C2A)=Sof(C3A)=Sof(H3AA)=Sof(C4A)=Sof(C5A)=Sof(H5A)=
 Sof(H6B)=Sof(C10A)=Sof(C11A)=Sof(H11C)=Sof(H11D)=Sof(C12A)=Sof(H12C)=Sof(H12D)=
 Sof(C13A)=Sof(H13D)=Sof(H13E)=Sof(H13F)=Sof(C25A)=Sof(H25C)=Sof(H25D)=
 Sof(C26A)=Sof(H26C)=Sof(H26D)=Sof(C27A)=Sof(H27D)=Sof(H27E)=Sof(H27F)=
 Sof(C28A)=Sof(H28D)=Sof(H28E)=Sof(H28F)=Sof(C29A)=Sof(H29D)=Sof(H29E)=
 Sof(H29F)=1-FVAR(2)
 Sof(O1)=Sof(C1)=Sof(C2)=Sof(C3)=Sof(H3A)=Sof(C4)=Sof(C5)=Sof(H5)=Sof(H6A)=
 Sof(C10)=Sof(C11)=Sof(H11A)=Sof(H11B)=Sof(C12)=Sof(H12A)=Sof(H12B)=Sof(C13)=
 Sof(H13A)=Sof(H13B)=Sof(H13C)=Sof(C25)=Sof(H25A)=Sof(H25B)=Sof(C26)=Sof(H26A)=
 Sof(H26B)=Sof(C27)=Sof(H27A)=Sof(H27B)=Sof(H27C)=Sof(C28)=Sof(H28A)=Sof(H28B)=
 Sof(H28C)=Sof(C29)=Sof(H29A)=Sof(H29B)=Sof(H29C)=FVAR(2)
5.a Ternary CH refined with riding coordinates:
 C3(H3A), C3A(H3AA), C5(H5), C5A(H5A), C6(H6A), C6(H6B), C17(H17), C19(H19),
 C20(H20), C32(H32), C32A(H32A), C34(H34), C34A(H34A), C35(H35), C35(H35A),
 C46(H46), C48(H48), C49(H49)
5.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C11(H11A,H11B), C11A(H11C,H11D), C12(H12A,H12B), C12A(H12C,H12D),
  C14(H14A,H14B), C15(H15B,H15A), C18(H18A,H18B), C25(H25A,H25B), C25A(H25C,
 H25D), C26(H26A,H26B), C26A(H26C,H26D), C36(H36A,H36B), C40(H40A,H40B),
 C40A(H40C,H40D), C41(H41A,H41B), C41A(H41C,H41D), C43(H43A,H43B), C44(H44A,
 H44B), C47(H47A,H47B), C54(H54A,H54B), C54A(H54C,H54D), C55(H55A,H55B),
 C55A(H55C,H55D)
5.c Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C13A(H13D,H13E,H13F), C21(H21A,H21B,H21C), C22(H22A,H22B,
 H22C), C23(H23A,H23B,H23C), C24(H24A,H24B,H24C), C27(H27A,H27B,H27C),
 C27A(H27D,H27E,H27F), C28(H28A,H28B,H28C), C28A(H28D,H28E,H28F), C29(H29A,H29B,
 H29C), C29A(H29D,H29E,H29F), C42(H42A,H42B,H42C), C42A(H42D,H42E,H42F),
 C50(H50A,H50B,H50C), C51(H51A,H51B,H51C), C52(H52A,H52B,H52C), C53(H53A,H53B,
 H53C), C56(H56A,H56B,H56C), C56A(H56D,H56E,H56F), C57(H57A,H57B,H57C),
 C57A(H57D,H57E,H57F), C58(H58A,H58B,H58C), C58A(H58D,H58E,H58F)
5.d Idealised tetrahedral OH refined as rotating group:
 O2(H2), O3(H3), O5(H5B), O6(H6)
;
_shelx_res_checksum              32921
_shelx_hkl_checksum              57320
_shelx_fab_checksum              47668
_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 1.279
_oxdiff_exptl_absorpt_empirical_full_min 0.565