Limonoids from <i>Cipadessa baccifera</i>.
Yu, Jin-Hai; Zhang, Hua; Zhou, Bin; Zimbres, Flavia M.; Dalal, Seema; Liu, Qun-Fang; Cassera, Maria B.; Yue, Jian-Min; Journal of natural products  (2020) –; doi:10.1021/acs.jnatprod.9b00666

data_1558162
_publ_section_title
;
 Limonoids from <i>Cipadessa baccifera</i>.
;
_journal_name_full               'Journal of natural products'
_journal_paper_doi               10.1021/acs.jnatprod.9b00666
_journal_year                    2020
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C32 H44 O10'
_chemical_formula_sum            'C32 H44 O10'
_chemical_formula_weight         588.67
_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             2015-06-09
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.49070(10)
_cell_length_b                   9.26300(10)
_cell_length_c                   38.6476(6)
_cell_measurement_reflns_used    5742
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      67.89
_cell_measurement_theta_min      4.58
_cell_volume                     3039.61(7)
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.969
_diffrn_measured_fraction_theta_max 0.952
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0291
_diffrn_reflns_av_unetI/netI     0.0272
_diffrn_reflns_Laue_measured_fraction_full 0.969
_diffrn_reflns_Laue_measured_fraction_max 0.952
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       46
_diffrn_reflns_limit_l_min       -46
_diffrn_reflns_number            20035
_diffrn_reflns_point_group_measured_fraction_full 0.962
_diffrn_reflns_point_group_measured_fraction_max 0.940
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         69.680
_diffrn_reflns_theta_min         2.286
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.782
_exptl_absorpt_correction_T_max  0.7532
_exptl_absorpt_correction_T_min  0.5979
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0988 before and 0.0485 after correction.
The Ratio of minimum to maximum transmission is 0.7938.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_density_diffrn    1.286
_exptl_crystal_description       block
_exptl_crystal_F_000             1264
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.148
_refine_diff_density_min         -0.209
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details
;
 Flack x determined using 2033 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.05(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     388
_refine_ls_number_reflns         5399
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0429
_refine_ls_R_factor_gt           0.0406
_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^)+(0.0751P)^2^+0.2200P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1100
_refine_ls_wR_factor_ref         0.1121
_reflns_Friedel_coverage         0.718
_reflns_Friedel_fraction_full    0.954
_reflns_Friedel_fraction_max     0.924
_reflns_number_gt                5074
_reflns_number_total             5399
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np9b00666_si_002.cif
_cod_data_source_block           cu_dm15474_0m
_cod_database_code               1558162
_shelxl_version_number           2014-3
_shelx_estimated_absorpt_t_max   0.912
_shelx_estimated_absorpt_t_min   0.859
_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:
 C1(H1), C2(H2A), C2'(H2'), C3(H3), C5(H5), C9(H9), C11(H11), C17(H17)
2.b Secondary CH2 refined with riding coordinates:
 C3'(H3'A,H3'B), C6(H6A,H6B), C12(H12A,H12B), C15(H15A,H15B)
2.c Aromatic/amide H refined with riding coordinates:
 C21(H21), C22(H22), C23(H23)
2.d X=CH2 refined with riding coordinates:
 C30(H30A,H30B)
2.e Idealised Me refined as rotating group:
 C4'(H4'A,H4'B,H4'C), C5'(H5'A,H5'B,H5'C), C18(H18A,H18B,H18C), C19(H19A,H19B,
 H19C), C24(H24A,H24B,H24C), C28(H28A,H28B,H28C), C29(H29A,H29B,H29C)
2.f Idealised tetrahedral OH refined as rotating group:
 O2(H2), O7(H7)
;
_shelx_res_checksum              89288
_shelx_hkl_checksum              41336
_olex2_submission_special_instructions 'No special instructions were received'