Cucurbitane Glucosides from the Crude Extract of Siraitia grosvenorii with Moderate Effects on PGC-1α Promoter Activity.
Niu, Biao; Ke, Chang-Qiang; Li, Bo-Han; Li, Yuanyuan; Yi, Yongji; Luo, Yongwei; Shuai, Lin; Yao, Sheng; Lin, Li-Gen; Li, Jia; Ye, Yang; Journal of natural products 80 (2017) 1428–1435; doi:10.1021/acs.jnatprod.6b01086

data_1546200
_publ_section_title
;
 Cucurbitane Glucosides from the Crude Extract of Siraitia grosvenorii
 with Moderate Effects on PGC-1\a Promoter Activity.
;
_journal_issue                   5
_journal_name_full               'Journal of natural products'
_journal_page_first              1428
_journal_page_last               1435
_journal_paper_doi               10.1021/acs.jnatprod.6b01086
_journal_volume                  80
_journal_year                    2017
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C30 H52 O4, 4/3(H2 O), 0.5(C H4 O)'
_chemical_formula_sum            'C30.5 H60.33333 O5.83333'
_chemical_formula_weight         513.74
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_symmetry_space_group_name_Hall  'P 1'
_symmetry_space_group_name_H-M   'P 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2016-09-09
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2016.08.25 svn.r3337 for OlexSys, GUI svn.r5221)
;
_cell_angle_alpha                97.926(2)
_cell_angle_beta                 93.125(2)
_cell_angle_gamma                114.454(2)
_cell_formula_units_Z            6
_cell_length_a                   14.9136(6)
_cell_length_b                   14.9888(6)
_cell_length_c                   22.7918(9)
_cell_measurement_reflns_used    9890
_cell_measurement_temperature    170
_cell_measurement_theta_max      68.278
_cell_measurement_theta_min      3.291
_cell_volume                     4558.1(3)
_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)'
_diffrn_ambient_temperature      170
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0348
_diffrn_reflns_av_unetI/netI     0.0309
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            83600
_diffrn_reflns_point_group_measured_fraction_full 0.967
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_theta_full        63.998
_diffrn_reflns_theta_max         63.998
_diffrn_reflns_theta_min         3.281
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.594
_exptl_absorpt_correction_T_max  0.0652
_exptl_absorpt_correction_T_min  0.0054
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0808 before and 0.0611 after correction.
The Ratio of minimum to maximum transmission is 0.0828.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.123
_exptl_crystal_description       block
_exptl_crystal_F_000             1702
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.587
_refine_diff_density_min         -0.291
_refine_diff_density_rms         0.078
_refine_ls_abs_structure_details
;
 Flack x determined using 10316 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.02(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     2080
_refine_ls_number_reflns         29290
_refine_ls_number_restraints     2012
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0896
_refine_ls_R_factor_gt           0.0824
_refine_ls_shift/su_max          0.055
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1554P)^2^+0.4496P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2130
_refine_ls_wR_factor_ref         0.2199
_reflns_Friedel_coverage         0.937
_reflns_Friedel_fraction_full    0.936
_reflns_Friedel_fraction_max     0.936
_reflns_number_gt                25315
_reflns_number_total             29290
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np6b01086_si_002.cif
_cod_data_source_block           p
_cod_depositor_comments
;

2019-07-31
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C184 H326 O34'
_cod_original_formula_weight         3082.43
_cod_original_formula_moiety       '5(C30 H52 O4), C31 H54 O3, 8(O), 3(C H4 O)'
_cod_original_formula_units_Z            1
_cod_database_code               1546200
_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 C(H,H,H,H,H,H) groups, All O(H) groups, All O(H,H)
  groups
2. Restrained distances
 O14-H14P
 0.84 with sigma of 0.02
3. Rigid bond restraints
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
4. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms restrained to be isotropic: with sigma of 0.01 and sigma
for terminal atoms of 0.02
5. Others
 Fixed Sof: O34(0.5) H34A(0.5) C1AA(0.5) H1AA(0.5) H1AB(0.5) H1AC(0.5)
 H7AA(0.5) H7AB(0.5) C0AA(0.5) H0AA(0.5) H0AB(0.5) H0AC(0.5) O3AA(0.5)
 H3AA(0.5) H9AA(0.5) H9AB(0.5) H9AC(0.5) H9AD(0.5) H9AE(0.5) H9AF(0.5)
 O4AA(0.5) H4AA(0.5) C2AA(0.5) H2AA(0.5) H2AB(0.5) H2AC(0.5) O0AA(0.5)
 H0AD(0.5) C5AA(0.5) H5AA(0.5) H5AB(0.5) H5AC(0.5)
6.a Ternary CH refined with riding coordinates:
 C1(H1), C4(H4), C11(H11), C14(H14), C20(H20), C23(H23), C27(H27), C31(H31),
 C34(H34), C41(H41), C47(H47), C50(H50), C53(H53), C57(H57), C61(H61), C64(H64),
  C71(H71), C74(H74), C81(H81), C83(H83), C87(H87), C91(H91), C94(H94),
 C100(H100), C106(H106), C110(H110), C112(H112), C116(H116), C120(H120),
 C123(H123), C130(H130), C136(H136), C141(H141), C142(H142), C146(H146),
 C150(H150), C153(H153), C160(H160), C163(H163), C170(H170), C172(H172),
 C176(H176)
6.b Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C6(H6A,H6B), C10(H10A,H10B), C15(H15M,H15N), C21(H21A,H21B),
 C22(H22A,H22B), C25(H25A,H25B), C26(H26A,H26B), C35(H35A,H35B), C36(H36A,H36B),
  C40(H40A,H40B), C46(H46A,H46B), C51(H51A,H51B), C52(H52A,H52B), C55(H55A,
 H55B), C56(H56A,H56B), C62(H62A,H62B), C63(H63A,H63B), C70(H70A,H70B),
 C75(H75A,H75B), C79(H79A,H79B), C80(H80A,H80B), C85(H85A,H85B), C86(H86A,H86B),
  C95(H95A,H95B), C96(H96A,H96B), C101(H10C,H10D), C105(H10E,H10F), C108(H10J,
 H10K), C109(H10L,H10M), C114(H11H,H11I), C115(H11J,H11K), C121(H12A,H12B),
 C122(H12C,H12D), C129(H12K,H12L), C135(H13G,H13H), C139(H13O,H13P), C140(H14A,
 H14B), C144(H14F,H14G), C145(H14H,H14I), C151(H15A,H15B), C152(H15C,H15D),
 C159(H15K,H15L), C164(H16D,H16E), C168(H16I,H16J), C169(H16K,H16L), C174(H17G,
 H17H), C175(H17I,H17J)
6.c Aromatic/amide H refined with riding coordinates:
 C9(H9), C39(H39), C69(H69), C102(H102), C128(H128), C158(H158)
6.d Tetrahedral OH refined with riding coordinates:
 O7AA(H7AA), O7AA(H7AB), O3AA(H3AA), O4AA(H4AA), O0AA(H0AD)
6.e Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C8(H8A,H8B,H8C), C13(H13A,H13B,H13C), C18(H18D,H18E,H18F),
 C19(H19A,H19B,H19C), C24(H24A,H24B,H24C), C29(H29A,H29B,H29C), C30(H30A,H30B,
 H30C), C37(H37A,H37B,H37C), C38(H38A,H38B,H38C), C43(H43A,H43B,H43C), C48(H48A,
 H48B,H48C), C49(H49A,H49B,H49C), C54(H54A,H54B,H54C), C59(H59A,H59B,H59C),
 C60(H60A,H60B,H60C), C67(H67A,H67B,H67C), C68(H68A,H68B,H68C), C73(H73A,H73B,
 H73C), C78(H78A,H78B,H78C), C82(H82A,H82B,H82C), C84(H84A,H84B,H84C), C89(H89A,
 H89B,H89C), C90(H90A,H90B,H90C), C97(H97A,H97B,H97C), C98(H98A,H98B,H98C),
 C107(H10G,H10H,H10I), C111(H11B,H11C,H11D), C113(H11E,H11F,H11G), C118(H11L,
 H11M,H11N), C119(H11O,H11P,H11Q), C126(H12E,H12F,H12G), C127(H12H,H12I,H12J),
 C132(H13D,H13E,H13F), C137(H13I,H13J,H13K), C138(H13L,H13M,H13N), C143(H14C,
 H14D,H14E), C148(H14J,H14K,H14L), C149(H14M,H14N,H14O), C156(H15E,H15F,H15G),
 C157(H15H,H15I,H15J), C162(H16A,H16B,H16C), C167(H16F,H16G,H16H), C171(H17A,
 H17B,H17C), C173(H17D,H17E,H17F), C178(H17K,H17L,H17M), C179(H17N,H17O,H17P),
 C181(H18G,H18H,H18I), C182(H18A,H18B,H18C), C1AA(H1AA,H1AB,H1AC), C0AA(H0AA,
 H0AB,H0AC), C9AA(H9AA,H9AB,H9AC), C9AA(H9AD,H9AE,H9AF), C2AA(H2AA,H2AB,H2AC),
 C5AA(H5AA,H5AB,H5AC)
6.f Idealised tetrahedral OH refined as rotating group:
 O1(H1A), O2(H2), O3(H3), O4(H4A), O5(H5), O6(H6), O7(H7), O8(H8), O9(H9A),
 O10(H10), O11(H11A), O12(H12), O13(H13), O15(H15), O16(H16), O17(H17),
 O18(H18), O19(H19), O20(H20A), O21(H21), O22(H22), O23(H23A), O34(H34A)
;
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'