Longipetalol A: A Highly Modified Triterpenoid from <i>Dichapetalum longipetalum</i>.
Zhang, Dong-Li; Li, Min; Han, Gui-Fang; Li, Shao-Yong; Jin, De-Jun; Tang, Sheng-An; Journal of natural products  (2021) –; doi:10.1021/acs.jnatprod.1c00068

data_1562339
_publ_section_title
;
 Longipetalol A: A Highly Modified Triterpenoid from <i>Dichapetalum
 longipetalum</i>.
;
_journal_name_full               'Journal of natural products'
_journal_paper_doi               10.1021/acs.jnatprod.1c00068
_journal_year                    2021
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C38 H44 O9, 2(C H4 O)'
_chemical_formula_sum            'C40 H52 O11'
_chemical_formula_weight         708.81
_space_group_crystal_system      hexagonal
_space_group_IT_number           169
_space_group_name_Hall           'P 61'
_space_group_name_H-M_alt        'P 61'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2020-11-07
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            6
_cell_length_a                   10.56998(5)
_cell_length_b                   10.56998(5)
_cell_length_c                   56.6723(3)
_cell_measurement_reflns_used    44644
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      73.7630
_cell_measurement_theta_min      3.9580
_cell_volume                     5483.40(5)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      294.15
_diffrn_detector                 Pilatus
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_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    -48.00 -23.00   0.50    0.50    --    5.00 -52.00 117.00   50
  2  \w     64.00  90.00   0.50    0.50    --    5.00  16.00   5.00   52
  3  \w    -35.00  51.00   0.50    0.50    --  -38.60  16.00   5.00  172
  4  \w   -108.00 -15.00   0.50    0.50    --  -38.60 -52.00 117.00  186
  5  \w    -98.00 -72.00   0.50    1.00    -- -110.00  26.00 -67.00   52
  6  \w   -153.00-127.00   0.50    1.00    -- -110.00 -26.00 129.00   52
  7  \w   -194.00-150.00   0.50    1.00    -- -110.00 -16.00-165.00   88
  8  \w   -118.00 -86.00   0.50    1.00    -- -110.00 -52.00 117.00   64
  9  \w   -134.00 -99.00   0.50    1.00    -- -110.00  26.00 -67.00   70
 10  \w    -92.00 -66.00   0.50    1.00    -- -110.00  16.00   5.00   52
 11  \w   -187.00-148.00   0.50    1.00    -- -110.00 -52.00 117.00   78
 12  \w   -135.00-102.00   0.50    1.00    -- -110.00 -16.00-165.00   66
 13  \w    -79.00 -53.00   0.50    1.00    -- -110.00  52.00 -96.00   52
 14  \w     13.00  38.00   0.50    0.50    --    5.00  52.00 -96.00   50
 15  \w    -24.00   2.00   0.50    0.50    --    5.00 -26.00 129.00   52
 16  \w     40.00  71.00   0.50    0.50    --    5.00  38.00 120.00   62
 17  \w     13.00  38.00   0.50    0.50    --    5.00  26.00 -67.00   50
 18  \w   -128.00 -14.00   0.50    0.50    --  -38.60 -67.00 -52.91  228
 19  \w   -116.00 -90.00   0.50    1.00    -- -110.00 -56.00   1.51   52
 20  \w   -116.00 -87.00   0.50    1.00    -- -110.00 -43.00 -40.99   58
 21  \w   -192.00-150.00   0.50    1.00    -- -110.00 -56.00   1.51   84
 22  \w   -194.00-168.00   0.50    1.00    -- -110.00 -43.00 -40.99   52
 23  \w   -116.00 -90.00   0.50    1.00    -- -110.00 -58.00  23.50   52
 24  \w   -151.00 -88.00   0.50    1.00    -- -110.00 -57.00 -60.00  126
 25  \w   -199.00-153.00   0.50    1.00    -- -110.00 -26.00 145.68   92
 26  \w   -134.00 -99.00   0.50    1.00    -- -110.00  38.00 -90.00   70
 27  \w   -181.00-111.00   0.50    1.00    -- -110.00 -72.00  60.00  140
 28  \w   -112.00 -86.00   0.50    1.00    -- -110.00 -72.00 -60.00   52
 29  \w   -123.00 -90.00   0.50    1.00    -- -110.00 -53.00 -82.11   66
 30  \w   -193.00-153.00   0.50    1.00    -- -110.00 -53.00 -82.11   80
 31  \w   -199.00-174.00   0.50    1.00    -- -110.00 -58.00  23.50   50
 32  \w   -134.00 -21.00   0.50    1.00    -- -110.00  72.00 -60.00  226
 33  \w   -182.00-129.00   0.50    1.00    -- -110.00 -60.00  -9.43  106
 34  \w   -186.00-161.00   0.50    1.00    -- -110.00 -27.00 120.12   50
 35  \w   -129.00 -88.00   0.50    1.00    -- -110.00 -27.00 120.12   82
 36  \w   -170.00-144.00   0.50    1.00    -- -110.00 -34.00 -77.65   52
 37  \w   -170.00-144.00   0.50    1.00    -- -110.00 -72.00-135.72   52
 38  \w   -133.00 -86.00   0.50    1.00    -- -110.00 -72.00-135.72   94
 39  \w   -198.00-149.00   0.50    1.00    -- -110.00 -38.00  30.00   98
 40  \w   -122.00 -92.00   0.50    1.00    -- -110.00 -55.00 -39.10   60
 41  \w    -74.00 -41.00   0.50    1.00    -- -110.00  38.00 -90.00   66
 42  \w   -181.00-152.00   0.50    1.00    -- -110.00 -44.00  58.25   58
 43  \w   -125.00 -99.00   0.50    1.00    -- -110.00 -44.00  58.25   52
 44  \w   -185.00-159.00   0.50    1.00    -- -110.00 -55.00 -39.10   52
 45  \w   -154.00 -86.00   0.50    1.00    -- -110.00 -19.00 150.00  136
 46  \w   -168.00 -87.00   0.50    1.00    -- -110.00 -72.00 -30.00  162
 47  \w   -134.00 -70.00   0.50    1.00    -- -110.00  57.00 -60.00  128
 48  \w    -66.00 -21.00   0.50    1.00    -- -110.00  57.00 -60.00   90
 49  \w   -196.00-144.00   0.50    1.00    -- -110.00 -19.00-120.00  104
 50  \w   -126.00-100.00   0.50    1.00    -- -110.00 -19.00-120.00   52
 51  \w   -116.00 -91.00   0.50    1.00    -- -110.00 -57.00 -30.00   50
 52  \w   -164.00-120.00   0.50    1.00    -- -110.00 -53.00  96.60   88
 53  \w   -127.00 -86.00   0.50    1.00    -- -110.00 -35.00  -7.87   82
 54  \w   -158.00 -86.00   0.50    1.00    -- -110.00 -48.00  30.95  144
 55  \w   -174.00-148.00   0.50    1.00    -- -110.00 -57.00 -97.50   52
 56  \w   -119.00 -86.00   0.50    1.00    -- -110.00 -57.00 -97.50   66
 57  \w    -81.00 -55.00   0.50    1.00    -- -110.00  49.00-139.23   52
 58  \w   -166.00-140.00   0.50    1.00    -- -110.00 -18.00  70.82   52
 59  \w   -139.00-113.00   0.50    1.00    -- -110.00 -18.00  70.82   52
 60  \w   -108.00 -21.00   0.50    1.00    -- -110.00  72.00-180.00  174
 61  \w   -160.00-116.00   0.50    1.00    -- -110.00   0.00 -30.00   88
 62  \w    -69.00 -21.00   0.50    1.00    -- -110.00   0.00 -30.00   96
 63  \w    -94.00 -68.00   0.50    1.00    -- -110.00  57.00 -90.00   52
 64  \w   -133.00 -96.00   0.50    1.00    -- -110.00  38.00 150.00   74
 65  \w   -147.00-121.00   0.50    1.00    -- -110.00 -38.00 -30.00   52
 66  \w   -114.00 -86.00   0.50    1.00    -- -110.00 -38.00 -30.00   56
 67  \w   -112.00 -86.00   0.50    1.00    -- -110.00 -38.00 150.00   52
 68  \w   -193.00-141.00   0.50    1.00    -- -110.00 -72.00 -60.00  104
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku Xtalab P200'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1422479000
_diffrn_orient_matrix_UB_12      -0.0059879000
_diffrn_orient_matrix_UB_13      -0.0020842000
_diffrn_orient_matrix_UB_21      0.0081579000
_diffrn_orient_matrix_UB_22      0.0359159000
_diffrn_orient_matrix_UB_23      -0.0264987000
_diffrn_orient_matrix_UB_31      0.0895686000
_diffrn_orient_matrix_UB_32      0.1642695000
_diffrn_orient_matrix_UB_33      0.0057137000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0286
_diffrn_reflns_av_unetI/netI     0.0159
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       70
_diffrn_reflns_limit_l_min       -70
_diffrn_reflns_number            74284
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.107
_diffrn_reflns_theta_min         4.682
_diffrn_source                   'rotating anode'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.763
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.57193
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.288
_exptl_crystal_description       block
_exptl_crystal_F_000             2280
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.264
_refine_diff_density_min         -0.224
_refine_diff_density_rms         0.028
_refine_ls_abs_structure_details
;
 Flack x determined using 3503 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.05(3)
_refine_ls_extinction_coef       0.00089(14)
_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   1.053
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     502
_refine_ls_number_reflns         7391
_refine_ls_number_restraints     67
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0363
_refine_ls_R_factor_gt           0.0361
_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^)+(0.0604P)^2^+0.6318P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1023
_refine_ls_wR_factor_ref         0.1025
_reflns_Friedel_coverage         0.973
_reflns_Friedel_fraction_full    0.993
_reflns_Friedel_fraction_max     0.993
_reflns_number_gt                7342
_reflns_number_total             7391
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np1c00068_si_002.cif
_cod_data_source_block           p20201104d
_cod_original_cell_volume        5483.40(6)
_cod_database_code               1562339
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.875
_shelx_estimated_absorpt_t_min   0.862
_reflns_odcompleteness_completeness 99.01
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_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
 C40-O11 = O11A-C40A
 1.45 with sigma of 0.01
 C27-HZ
 0.95 with sigma of 0.01
 H6AA-H7AA
 1.55 with sigma of 0.01
 C30-H6AA = C30-H7AA
 0.95 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
O11 \\sim C40 \\sim C40A \\sim O11A: within 1.7A with sigma of 0.01 and sigma
for terminal atoms of 0.02
Uanis(O11) \\sim Ueq, Uanis(C40A) \\sim Ueq, Uanis(C40) \\sim Ueq, Uanis(O11A)
\\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
4. Others
 Sof(C40A)=Sof(H40A)=Sof(H40B)=Sof(H40C)=Sof(O11A)=Sof(H11A)=1-FVAR(1)
 Sof(O11)=Sof(H1CA)=Sof(C40)=Sof(H2CA)=Sof(H3CA)=Sof(H4CA)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C11(HI), C13(HJ), C23(HW), C34(H0BA)
5.b Secondary CH2 refined with riding coordinates:
 C8(HG,HH), C17(HQ,HR), C21(HS,HT), C22(HU,HV), C33(H8AA,H9AA), C38(H5BA,H6BA)
5.c Aromatic/amide H refined with riding coordinates:
 C1(HB), C2(HC), C3(HD), C4(HE), C5(HF), C25(HX), C26(HY), C35(H1BA)
5.d Idealised Me refined as rotating group:
 C15(HK,HL,HM), C16(HN,HO,HP), C28(H0AA,H1AA,H2AA), C29(H3AA,H4AA,H5AA),
 C37(H2BA,H3BA,H4BA), C39(H8BA,H9BA,H0CA), C40(H2CA,H3CA,H4CA), C40A(H40A,H40B,
 H40C)
5.e Idealised tetrahedral OH refined as rotating group:
 O8(H), O9(HA), O10(H7BA), O11(H1CA), O11A(H11A)
;
_shelx_res_checksum              2538
_shelx_hkl_checksum              70669
_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 1.670
_oxdiff_exptl_absorpt_empirical_full_min 0.738