Structural Revision of Guttiferone F and 30-epi-Cambogin
Zheng, Dan; Jiang, Jia-Ming; Chen, Si-Min; Wan, Shi-Jie; Ren, Han-Gui; Chen, Gan; Xu, Gang; Zhou, Hua; Zhang, Hong; Xu, Hong-Xi; Journal of Natural Products  (2021) –; doi:10.1021/acs.jnatprod.0c01031

data_1560945
_publ_section_title
;
 Structural Revision of Guttiferone F and 30-epi-Cambogin
;
_journal_name_full               'Journal of Natural Products'
_journal_paper_doi               10.1021/acs.jnatprod.0c01031
_journal_year                    2021
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C38 H50 O6'
_chemical_formula_sum            'C38 H50 O6'
_chemical_formula_weight         602.78
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2019-11-01
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 93.6280(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.5894(3)
_cell_length_b                   11.1597(3)
_cell_length_c                   20.4193(5)
_cell_measurement_reflns_used    9047
_cell_measurement_temperature    173
_cell_measurement_theta_max      68.383
_cell_measurement_theta_min      4.518
_cell_volume                     3317.87(14)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 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 2014/4 (Sheldrick, 2014)'
_diffrn_ambient_temperature      173.01
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0209
_diffrn_reflns_av_unetI/netI     0.0294
_diffrn_reflns_Laue_measured_fraction_full 0.979
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            22097
_diffrn_reflns_point_group_measured_fraction_full 0.952
_diffrn_reflns_point_group_measured_fraction_max 0.947
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.435
_diffrn_reflns_theta_min         3.035
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.636
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.6893
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0743 before and 0.0423 after correction. The Ratio of minimum to maximum transmission is 0.9153. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.207
_exptl_crystal_description       block
_exptl_crystal_F_000             1304
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.175
_refine_diff_density_min         -0.196
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details
;
 Flack x determined using 4903 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.06(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     817
_refine_ls_number_reflns         11551
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          0.0314
_refine_ls_R_factor_gt           0.0295
_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^)+(0.0480P)^2^+0.3210P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0783
_refine_ls_wR_factor_ref         0.0826
_reflns_Friedel_coverage         0.839
_reflns_Friedel_fraction_full    0.922
_reflns_Friedel_fraction_max     0.915
_reflns_number_gt                11174
_reflns_number_total             11551
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np0c01031_si_003.cif
_cod_data_source_block           170423zzy6_0m
_cod_database_code               1560945
_shelx_shelxl_version_number     2018/3
_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:
 C45(H45), C7(H7), C68(H68), C30(H30)
2.b Secondary CH2 refined with riding coordinates:
 C62(H62A,H62B), C24(H24A,H24B), C67(H67A,H67B), C46(H46A,H46B), C6(H6A,H6B),
 C19(H19A,H19B), C57(H57A,H57B), C29(H29A,H29B), C72(H72A,H72B), C34(H34A,H34B)
2.c Aromatic/amide H refined with riding coordinates:
 C50(H50), C53(H53), C12(H12), C16(H16), C25(H25), C54(H54), C63(H63),
 C20(H20), C73(H73), C15(H15), C35(H35), C58(H58)
2.d Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C55(H55A,H55B,H55C), C56(H56A,H56B,H56C), C71(H71A,H71B,
 H71C), C17(H17A,H17B,H17C), C23(H23A,H23B,H23C), C70(H70A,H70B,H70C), C28(H28A,
 H28B,H28C), C22(H22A,H22B,H22C), C32(H32A,H32B,H32C), C61(H61A,H61B,H61C),
 C33(H33A,H33B,H33C), C27(H27A,H27B,H27C), C66(H66A,H66B,H66C), C75(H75A,H75B,
 H75C), C76(H76A,H76B,H76C), C60(H60A,H60B,H60C), C38(H38A,H38B,H38C), C65(H65A,
 H65B,H65C), C37(H37A,H37B,H37C)
2.e Idealised tetrahedral OH refined as rotating group:
 O4(H4), O11(H11), O3(H3), O10(H10)
;
_olex2_submission_special_instructions 'No special instructions were received'