Antcamphorols A‒K, Cytotoxic and ROS Scavenging Triterpenoids from Antrodia camphorata
Li, Bin; Kuang, Yi; He, Jun-Bin; Tang, Rui; Xu, Lu-Lu; Leung, Chung-Hang; Ma, Dik-Lung; Qiao, Xue; Ye, Min; Journal of Natural Products  (2019) –; doi:10.1021/acs.jnatprod.9b00580

data_1556857
_publ_section_title
;
 Antcamphorols A--K, Cytotoxic and ROS Scavenging Triterpenoids from
 Antrodia camphorata
;
_journal_name_full               'Journal of Natural Products'
_journal_paper_doi               10.1021/acs.jnatprod.9b00580
_journal_year                    2019
_chemical_formula_moiety         'C31 H50 O3, C H4 O'
_chemical_formula_sum            'C32 H54 O4'
_chemical_formula_weight         502.75
_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   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2017-07-07
_audit_creation_method
;
  Olex2 1.2
  (compiled Dec  5 2012 16:20:19, GUI svn.r4385)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.2668(8)
_cell_length_b                   14.648(3)
_cell_length_c                   31.434(5)
_cell_measurement_reflns_used    2623
_cell_measurement_temperature    106.7
_cell_measurement_theta_max      71.0210
_cell_measurement_theta_min      3.0114
_cell_volume                     2885.5(8)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
XL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
;
XS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      106.7
_diffrn_detector_area_resol_mean 16.0971
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_details
;
  1 omega  -39.00   10.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000  111.0000  -30.0000 49

  2 omega  -13.00   13.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000  111.0000 -120.0000 26

  3 omega   23.00   57.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000   77.0000   60.0000 34

  4 omega   43.00  104.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       36.7919   77.0000  -90.0000 61

  5 omega   24.00   50.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       36.7919   37.0000   90.0000 26

  6 omega   18.00  106.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       36.7919   37.0000  120.0000 88

  7 omega   10.00   36.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       36.7919   77.0000  -90.0000 26

  8 omega    1.00   27.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       36.7919 -102.0000  -95.0000 26

  9 omega   50.00   97.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000   30.0000 47

 10 omega   41.00   79.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000    0.0000 38

 11 omega   47.00   97.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  -60.0000 50

 12 omega  104.00  172.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000  -30.0000 68

 13 omega   56.00   98.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  150.0000 42

 14 omega  150.00  176.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000 -180.0000 26

 15 omega   47.00  171.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000    0.0000  -60.0000 124
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0243971000
_diffrn_orient_matrix_UB_12      -0.0715581000
_diffrn_orient_matrix_UB_13      -0.0355543000
_diffrn_orient_matrix_UB_21      0.1185426000
_diffrn_orient_matrix_UB_22      0.0705968000
_diffrn_orient_matrix_UB_23      -0.0276289000
_diffrn_orient_matrix_UB_31      0.2136985000
_diffrn_orient_matrix_UB_32      -0.0308032000
_diffrn_orient_matrix_UB_33      0.0192501000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0291
_diffrn_reflns_av_unetI/netI     0.0544
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_number            9210
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.323
_diffrn_reflns_theta_min         3.329
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.572
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85229
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.157
_exptl_crystal_F_000             1112
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.222
_refine_diff_density_min         -0.183
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details
;
 Flack x determined using 1847 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.05(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     369
_refine_ls_number_reflns         5442
_refine_ls_number_restraints     78
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0523
_refine_ls_R_factor_gt           0.0463
_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^)+(0.0534P)^2^+0.3729P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1114
_refine_ls_wR_factor_ref         0.1159
_reflns_Friedel_coverage         0.711
_reflns_Friedel_fraction_full    0.992
_reflns_Friedel_fraction_max     0.948
_reflns_number_gt                4918
_reflns_number_total             5442
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np9b00580_si_002.cif
_cod_data_source_block           exp_5024
_cod_database_code               1556857
_reflns_odcompleteness_completeness 99.80
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Others
 Fixed Uiso: H1(0.044) H3(0.05) H1A(0.027) H8A(0.033) H8B(0.033) H8C(0.033)
 H9A(0.03) H9B(0.03) H10A(0.032) H10B(0.032) H12A(0.026) H12B(0.026)
 H13A(0.031) H13B(0.031) H14A(0.031) H14B(0.031) H16A(0.028) H16B(0.028)
 H17A(0.028) H17B(0.028) H20A(0.026) H20B(0.026) H21(0.025) H22A(0.046)
 H22B(0.046) H22C(0.046) H23(0.025) H24A(0.045) H24B(0.045) H24C(0.045)
 H26(0.025) H27A(0.045) H27B(0.045) H27C(0.045) H29A(0.042) H29B(0.042)
 H29C(0.042) H30A(0.028) H30B(0.028) H31A(0.032) H31B(0.032) H32A(0.041)
 H32B(0.041) H33(0.029) H34A(0.05) H34B(0.05) H34C(0.05) H35A(0.046)
 H35B(0.046) H35C(0.046) H4(0.055) H36A(0.063) H36B(0.063) H36C(0.063)
 H34D(0.04) H34E(0.04) H34F(0.04) H33A(0.025) H35D(0.044) H35E(0.044)
 H35F(0.044) H36D(0.063) H36E(0.063) H36F(0.063)
 Fixed X: H1(0.0053) H3(0.6845) H1A(0.2071) H8A(0.1503) H8B(0.0616)
 H8C(0.1336) H9A(0.2273) H9B(0.392) H10A(-0.1385) H10B(0.0608) H12A(0.6279)
 H12B(0.3751) H13A(0.1412) H13B(0.3443) H14A(0.8092) H14B(0.5572) H16A(0.7778)
 H16B(0.5427) H17A(0.7022) H17B(0.8402) H20A(0.3968) H20B(0.5759) H21(0.2636)
 H22A(0.6176) H22B(0.5756) H22C(0.7995) H23(0.6962) H24A(-0.3141) H24B(-0.3195)
 H24C(-0.2912) H26(0.3848) H27A(-0.1438) H27B(-0.1882) H27C(-0.2438)
 H29A(0.2271) H29B(0.0224) H29C(0.0152) H30A(0.1104) H30B(0.2952) H31A(-0.0588)
 H31B(0.0762) H32A(0.9528) H32B(0.8998) H33(0.6111) H34A(0.2657) H34B(0.3198)
 H34C(0.3194) H35A(0.6946) H35B(0.6917) H35C(0.8756) H4(-0.3546) H36A(-0.486)
 H36B(-0.6764) H36C(-0.4398) H34D(0.5591) H34E(0.3451) H34F(0.3504)
 H33A(0.3762) H35D(0.6796) H35E(0.5709) H35F(0.779) H36D(-0.3882) H36E(-0.5952)
 H36F(-0.3648)
 Fixed Y: H1(-0.1587) H3(-0.6068) H1A(-0.194) H8A(-0.2317) H8B(-0.2674) H8C(-
 0.339) H9A(-0.0427) H9B(-0.0526) H10A(-0.3048) H10B(-0.3415) H12A(-0.4521)
 H12B(-0.4407) H13A(-0.3757) H13B(-0.3798) H14A(-0.3587) H14B(-0.3413) H16A(-
 0.1672) H16B(-0.1478) H17A(-0.2424) H17B(-0.3221) H20A(-0.4153) H20B(-0.3558)
 H21(-0.1402) H22A(-0.0271) H22B(0.0053) H22C(-0.0397) H23(-0.3074) H24A(-
 0.0846) H24B(-0.1775) H24C(-0.0818) H26(-0.301) H27A(-0.3208) H27B(-0.2137)
 H27C(-0.2643) H29A(-0.0334) H29B(-0.0276) H29C(0.0167) H30A(-0.3733) H30B(-
 0.3072) H31A(-0.0823) H31B(-0.0106) H32A(-0.5115) H32B(-0.4702) H33(-0.5919)
 H34A(-0.54) H34B(-0.5506) H34C(-0.4516) H35A(-0.4434) H35B(-0.5491) H35C(-
 0.5107) H4(-0.1855) H36A(-0.3198) H36B(-0.2843) H36C(-0.2925) H34D(-0.6372)
 H34E(-0.615) H34F(-0.6038) H33A(-0.4591) H35D(-0.4268) H35E(-0.5165) H35F(-
 0.5252) H36D(-0.3091) H36E(-0.2658) H36F(-0.2228)
 Fixed Z: H1(-0.0795) H3(-0.4538) H1A(-0.1292) H8A(-0.3932) H8B(-0.3485) H8C(-
 0.3842) H9A(-0.3013) H9B(-0.2628) H10A(-0.1586) H10B(-0.1317) H12A(-0.4105)
 H12B(-0.406) H13A(-0.2887) H13B(-0.2582) H14A(-0.5207) H14B(-0.5202) H16A(-
 0.3984) H16B(-0.4171) H17A(-0.4707) H17B(-0.4493) H20A(-0.335) H20B(-0.3116)
 H21(-0.202) H22A(-0.3107) H22B(-0.3586) H22C(-0.3459) H23(-0.376) H24A(-
 0.1467) H24B(-0.1735) H24C(-0.1974) H26(-0.4428) H27A(-0.2608) H27B(-0.2658)
 H27C(-0.222) H29A(-0.1499) H29B(-0.1195) H29C(-0.1661) H30A(-0.2051) H30B(-
 0.1882) H31A(-0.259) H31B(-0.2313) H32A(-0.4994) H32B(-0.4535) H33(-0.5248)
 H34A(-0.5201) H34B(-0.5696) H34C(-0.548) H35A(-0.582) H35B(-0.5949) H35C(-
 0.5645) H4(-0.0809) H36A(-0.0841) H36B(-0.0545) H36C(-0.0357) H34D(-0.5304)
 H34E(-0.5561) H34F(-0.5055) H33A(-0.5402) H35D(-0.5817) H35E(-0.601) H35F(-
 0.5718) H36D(-0.0458) H36E(-0.0239) H36F(-0.015)
;
_shelx_estimated_absorpt_t_max   0.977
_shelx_estimated_absorpt_t_min   0.725
_shelx_hkl_checksum              67143
_shelx_res_checksum              25469
_shelx_shelxl_version_number     2014/7