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_1560944
_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, C2 H3 N'
_chemical_formula_sum            'C40 H53 N O6'
_chemical_formula_weight         643.83
_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   mixed
_atom_sites_solution_primary     dual
_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                 103.0290(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.8272(4)
_cell_length_b                   9.0795(3)
_cell_length_c                   19.3623(7)
_cell_measurement_reflns_used    7412
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      68.17
_cell_measurement_theta_min      17.203
_cell_volume                     1854.42(11)
_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 (Sheldrick, 2015)'
_diffrn_ambient_temperature      173.0
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.994
_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  0.0253
_diffrn_reflns_av_unetI/netI     0.0339
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            13031
_diffrn_reflns_point_group_measured_fraction_full 0.971
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.183
_diffrn_reflns_theta_min         2.342
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.607
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.6723
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1377 before and 0.0479 after correction. The Ratio of minimum to maximum transmission is 0.8927. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.153
_exptl_crystal_description       block
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.248
_refine_diff_density_min         -0.342
_refine_diff_density_rms         0.067
_refine_ls_abs_structure_details
;
 Flack x determined using 2559 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.14(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     444
_refine_ls_number_reflns         6546
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.099
_refine_ls_R_factor_all          0.0398
_refine_ls_R_factor_gt           0.0350
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0520P)^2^+0.1590P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0910
_refine_ls_wR_factor_ref         0.0943
_reflns_Friedel_coverage         0.823
_reflns_Friedel_fraction_full    0.944
_reflns_Friedel_fraction_max     0.938
_reflns_number_gt                6080
_reflns_number_total             6546
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np0c01031_si_002.cif
_cod_data_source_block           170423zzy5_0m
_cod_database_code               1560944
_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:
 C7(H7), C30(H30)
2.b Secondary CH2 refined with riding coordinates:
 C19(H19A,H19B), C6(H6A,H6B), C29(H29A,H29B), C24(H24A,H24B), C34(H34A,H34B)
2.c Aromatic/amide H refined with riding coordinates:
 C12(H12), C20(H20), C16(H16), C15(H15), C25(H25), C35(H35)
2.d Tetrahedral OH refined with riding coordinates:
 O1(H1)
2.e Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C17(H17A,H17B,H17C), C23(H23A,H23B,H23C), C22(H22A,H22B,
 H22C), C33(H33A,H33B,H33C), C27(H27A,H27B,H27C), C28(H28A,H28B,H28C), C39(H39A,
 H39B,H39C), C37(H37A,H37B,H37C), C38(H38A,H38B,H38C)
2.f Idealised tetrahedral OH refined as rotating group:
 O4(H4), O5(H5)
;
_olex2_submission_special_instructions 'No special instructions were received'