Buxaustroines A-N, a Series of 17(13→ 18)<i>abeo</i>-Cycloartenol Triterpenoidal Alkaloids from <i>Buxus austro-yunnanensis</i> and Their Cardioprotective Activities.
Xiang, Zhi-Nan; Yi, Wen-Qin; Wang, Yong-Long; Shao, Li-Dong; Zhang, Cheng-Qi; Yuan, Yan; Pan, Jun; Wan, Luo-Sheng; Chen, Jia-Chun; Journal of natural products 82 (2019) 3111–3120; doi:10.1021/acs.jnatprod.9b00652

data_1552751
_publ_section_title
;
 Buxaustroines A-N, a Series of 17(13\\rightarrow
 18)<i>abeo</i>-Cycloartenol Triterpenoidal Alkaloids from <i>Buxus
 austro-yunnanensis</i> and Their Cardioprotective Activities.
;
_journal_issue                   11
_journal_name_full               'Journal of natural products'
_journal_page_first              3111
_journal_page_last               3120
_journal_paper_doi               10.1021/acs.jnatprod.9b00652
_journal_volume                  82
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C25 H41 N O2'
_chemical_formula_sum            'C25 H41 N O2'
_chemical_formula_weight         387.59
_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   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2018-03-22
_audit_creation_method
;
Olex2 1.2
(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            4
_cell_length_a                   7.77446(8)
_cell_length_b                   13.53787(11)
_cell_length_c                   20.2762(2)
_cell_measurement_reflns_used    17791
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.4910
_cell_measurement_theta_min      3.2270
_cell_volume                     2134.06(4)
_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    'ShelXT (Sheldrick, 2015)'
_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 1.000
_diffrn_measured_fraction_theta_max 0.992
_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    -69.00  32.00   1.00    1.00    --  -40.98  57.00 120.00  101
  2  \w    -96.00  -2.00   1.00    1.00    --  -40.98 125.00-180.00   94
  3  \w     13.00 113.00   1.00    1.00    --   40.98  57.00  30.00  100
  4  \w     34.00 121.00   1.00    1.00    --  106.95-125.00-150.00   87
  5  \w     35.00 136.00   1.00    1.00    --  106.95 -61.00 -60.00  101
  6  \w     94.00 178.00   1.00    1.00    --  106.95 125.00-180.00   84
  7  \w     31.00 135.00   1.00    1.00    --  106.95 -30.00 -90.00  104
  8  \w     94.00 178.00   1.00    1.00    --  106.95 125.00 -30.00   84
  9  \w     31.00 140.00   1.00    1.00    --  106.95 -77.00   0.00  109
 10  \w   -113.00 -63.00   1.00    1.00    --  -40.98-142.00-151.00   50
 11  \w     13.00 113.00   1.00    1.00    --   40.98  57.00 -90.00  100
 12  \w     13.00 113.00   1.00    1.00    --   40.98  57.00 150.00  100
 13  \w     54.00 178.00   1.00    1.00    --  106.95  15.00-180.00  124
 14  \w     79.00 178.00   1.00    1.00    --  106.95  30.00 -60.00   99
 15  \w     74.00 178.00   1.00    1.00    --  106.95  77.00   0.00  104
 16  \w     81.00 128.00   1.00    1.00    --  106.95  45.00-120.00   47
 17  \w     78.00 178.00   1.00    1.00    --  106.95  61.00  60.00  100
;
_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      0.1374885000
_diffrn_orient_matrix_UB_12      0.0622245000
_diffrn_orient_matrix_UB_13      0.0356374000
_diffrn_orient_matrix_UB_21      -0.0964763000
_diffrn_orient_matrix_UB_22      0.0951388000
_diffrn_orient_matrix_UB_23      -0.0193500000
_diffrn_orient_matrix_UB_31      -0.1051526000
_diffrn_orient_matrix_UB_32      -0.0059128000
_diffrn_orient_matrix_UB_33      0.0642198000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0306
_diffrn_reflns_av_unetI/netI     0.0168
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            19908
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.555
_diffrn_reflns_theta_min         3.926
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.573
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72215
_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    1.206
_exptl_crystal_description       block
_exptl_crystal_F_000             856
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.242
_refine_diff_density_min         -0.219
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details
;
 Flack x determined using 1784 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.00(6)
_refine_ls_extinction_coef       0.0065(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     264
_refine_ls_number_reflns         4254
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0338
_refine_ls_R_factor_gt           0.0337
_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^)+(0.0592P)^2^+0.3324P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0883
_refine_ls_wR_factor_ref         0.0884
_reflns_Friedel_coverage         0.740
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.985
_reflns_number_gt                4237
_reflns_number_total             4254
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np9b00652_si_002.cif
_cod_data_source_block           40a
_cod_depositor_comments          'Adding full bibliography for 1552751.cif.'
_cod_database_code               1552751
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_max   0.934
_shelx_estimated_absorpt_t_min   0.924
_reflns_odcompleteness_completeness 99.95
_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:
 C3(H3), C5(H5), C17(H17), C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C1(H1B,H1C), C19(H19A,H19B), C18(H18A,H18B), C2(H2A,H2B),
 C11(H11A,H11B), C15(H15A,H15B), C7(H7A,H7B), C6(H6A,H6B), C20(H20A,H20B)
2.c Idealised Me refined as rotating group:
 C32(H32A,H32B,H32C), C00C(H00A,H00B,H00C), C31(H31A,H31B,H31C), C30(H30A,H30B,
 H30C), C21(H21A,H21B,H21C)
2.d Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_olex2_date_sample_data_collection 2018-03-22
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.387
_oxdiff_exptl_absorpt_empirical_full_min 0.709