Limonoids with Diverse Oxidation Patterns of C-12 Indicating a Complete Ring C-<i>seco</i> Biogenetic Pathway from <i>Munronia unifoliolata</i>.
Sun, Yunpeng; Li, Qiurong; Sun, Yujin; Cui, Letian; Wang, Yingying; Li, Yongyi; Luo, Jun; Kong, Lingyi; Journal of natural products 84 (2021) 2352–2365; doi:10.1021/acs.jnatprod.1c00519

data_1564535
_publ_section_title
;
 Limonoids with Diverse Oxidation Patterns of C-12 Indicating a Complete
 Ring C-<i>seco</i> Biogenetic Pathway from <i>Munronia unifoliolata</i>.
;
_journal_issue                   8
_journal_name_full               'Journal of natural products'
_journal_page_first              2352
_journal_page_last               2365
_journal_paper_doi               10.1021/acs.jnatprod.1c00519
_journal_volume                  84
_journal_year                    2021
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C35 H48 O15'
_chemical_formula_sum            'C35 H48 O15'
_chemical_formula_weight         708.73
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2020-09-29
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.05390(10)
_cell_length_b                   15.7616(3)
_cell_length_c                   26.6941(5)
_cell_measurement_reflns_used    9844
_cell_measurement_temperature    170
_cell_measurement_theta_max      74.63
_cell_measurement_theta_min      3.26
_cell_volume                     3388.61(10)
_computing_cell_refinement       'SAINT V8.40A (?, 2016)'
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_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      170.0
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0378
_diffrn_reflns_av_unetI/netI     0.0296
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            25791
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         74.624
_diffrn_reflns_theta_min         3.256
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.913
_exptl_absorpt_correction_T_max  0.7538
_exptl_absorpt_correction_T_min  0.6328
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1549 before and 0.0754 after correction. The Ratio of minimum to maximum transmission is 0.8395. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.389
_exptl_crystal_description       block
_exptl_crystal_F_000             1512
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_platon_squeeze_details
;
TITL cu_22020763_0m_a.res in P2(1)2(1)2(1)
CELL    8.0539   15.7616   26.6941     90.00     90.00     90.00
SPGR P212121
Q101 0.793 0.395 0.045 !       1.79 eA-3
C102 0.932 0.388 0.018 !       0.81 eA-3
;
_refine_diff_density_max         0.249
_refine_diff_density_min         -0.229
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details
;
 Flack x determined using 2642 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.06(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     464
_refine_ls_number_reflns         6812
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0349
_refine_ls_R_factor_gt           0.0321
_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^)+(0.0378P)^2^+0.7810P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0787
_refine_ls_wR_factor_ref         0.0809
_reflns_Friedel_coverage         0.760
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.975
_reflns_number_gt                6431
_reflns_number_total             6812
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np1c00519_si_001.cif
_cod_data_source_block           cu_22020763_0m_sq
_cod_database_code               1564535
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.956
_shelx_estimated_absorpt_t_min   0.875
_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:
 C5(H5), C3(H3), C6(H6A), C7(H7), C11(H11), C9(H9), C17(H17), C1(H1),
 C15(H15A), C21(H21), C23(H23)
2.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C19(H19A,H19B), C28(H28A,H28B), C2(H2A,H2B), C22(H22A,H22B),
 C16(H16A,H16B)
2.c Aromatic/amide H refined with riding coordinates:
 C3'(H3')
2.d Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C26(H26A,H26B,H26C), C31(H31A,H31B,H31C), C30(H30A,H30B,
 H30C), C4'(H4'A,H4'B,H4'C), C24(H24A,H24B,H24C), C5'(H5'A,H5'B,H5'C)
2.e Idealised tetrahedral OH refined as rotating group:
 O6(H6), O4(H4)
;
_platon_squeeze_void_probe_radius 1.20
_olex2_submission_special_instructions 'No special instructions were received'