Linderaggrenolides A–N, Oxygen-Conjugated Sesquiterpenoid Dimers from the Roots of Lindera aggregata
Liu, Xin; Fu, Jing; Yang, Ji; Huang, Ancheng C.; Li, Run-Feng; Bai, Li-Ping; Liu, Liang; Jiang, Zhi-Hong; Zhu, Guo-Yuan; ACS Omega 6 (2021) 5898–5909; doi:10.1021/acsomega.0c06349

data_4518528
_publ_section_title
;
 Linderaggrenolides A--N, Oxygen-Conjugated Sesquiterpenoid Dimers from
 the Roots of Lindera aggregata
;
_journal_issue                   8
_journal_name_full               'ACS Omega'
_journal_page_first              5898
_journal_page_last               5909
_journal_paper_doi               10.1021/acsomega.0c06349
_journal_volume                  6
_journal_year                    2021
_chemical_compound_source        'Lindera aggregata'
_chemical_formula_moiety         'C31 H38 O8'
_chemical_formula_sum            'C31 H38 O8'
_chemical_formula_weight         538.61
_chemical_name_systematic        'Linderaggrenolide A'
_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     direct
_audit_creation_date             2018-09-06
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-10-15 deposited with the CCDC.	2021-01-01 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.04240(5)
_cell_length_b                   13.88872(7)
_cell_length_c                   25.03583(14)
_cell_measurement_reflns_used    24782
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      73.5370
_cell_measurement_theta_min      3.5000
_cell_volume                     2796.47(3)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 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_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w   -117.00 -51.00   1.00    1.00    --  -41.11-158.00  27.00   66
  2  \w   -113.00 -13.00   1.00    1.00    --  -41.11 -57.00 -90.00  100
  3  \w    -74.00  35.00   1.00    1.00    --  -41.11  77.00  60.00  109
  4  \w     94.00 178.00   1.00    1.00    --  106.95 125.00 150.00   84
  5  \w     34.00 121.00   1.00    1.00    --  106.95-125.00-120.00   87
  6  \w     31.00 135.00   1.00    1.00    --  106.95 -30.00 -90.00  104
  7  \w     31.00 135.00   1.00    1.00    --  106.95 -30.00   0.00  104
  8  \w     25.00 109.00   1.00    1.00    --  106.95 -95.00 -90.00   84
  9  \w     34.00 133.00   1.00    1.00    --  106.95 -45.00-150.00   99
 10  \w   -115.00 -17.00   1.00    1.00    --  -41.11 -38.00  60.00   98
 11  \w   -113.00 -13.00   1.00    1.00    --  -41.11 -57.00-180.00  100
 12  \w     79.00 178.00   1.00    1.00    --  106.95  30.00  30.00   99
 13  \w     78.00 178.00   1.00    1.00    --  106.95  61.00 -60.00  100
 14  \w     74.00 178.00   1.00    1.00    --  106.95  77.00-120.00  104
 15  \w     41.00 178.00   1.00    1.00    --  106.95  13.00 172.00  137
 16  \w   -113.00 -13.00   1.00    1.00    --  -41.11 -57.00   0.00  100
 17  \w      1.00  82.00   1.00    1.00    --   41.11 -99.00 -90.00   81
 18  \w     78.00 178.00   1.00    1.00    --  106.95  61.00-150.00  100
 19  \w     81.00 128.00   1.00    1.00    --  106.95  45.00  60.00   47
 20  \w     25.00 109.00   1.00    1.00    --  106.95 -95.00  90.00   84
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0008462000
_diffrn_orient_matrix_UB_12      -0.0785129000
_diffrn_orient_matrix_UB_13      -0.0434765000
_diffrn_orient_matrix_UB_21      0.0336929000
_diffrn_orient_matrix_UB_22      -0.0770629000
_diffrn_orient_matrix_UB_23      0.0429143000
_diffrn_orient_matrix_UB_31      -0.1885513000
_diffrn_orient_matrix_UB_32      -0.0140924000
_diffrn_orient_matrix_UB_33      0.0074741000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0340
_diffrn_reflns_av_unetI/netI     0.0191
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            32118
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.661
_diffrn_reflns_theta_min         3.531
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.750
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.71800
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.279
_exptl_crystal_description       block
_exptl_crystal_F_000             1152
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: MeOH'
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.151
_refine_diff_density_min         -0.243
_refine_diff_density_rms         0.049
_refine_ls_abs_structure_details
;
 Flack x determined using 2331 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.08(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     375
_refine_ls_number_reflns         5585
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0311
_refine_ls_R_factor_gt           0.0307
_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^)+(0.0505P)^2^+0.4414P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0787
_refine_ls_wR_factor_ref         0.0790
_reflns_Friedel_coverage         0.751
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.984
_reflns_number_gt                5504
_reflns_number_total             5585
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ao0c06349_si_002.cif
_cod_data_source_block           16-6-3
_cod_database_code               4518528
_shelx_shelxl_version_number     2018/3
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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:
 C6(H6), C12'(H12'), C6'(H6'), C5(H5), C1(H1), C5'(H5'), C3(H3A), C1'(H1'),
 C3'(H3')
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C9'(H9'A,H9'B), C2(H2A,H2B), C2'(H2'A,H2'B)
2.c Idealised Me refined as rotating group:
 C13'(H13A,H13B,H13C), C14(H14A,H14B,H14C), C14'(H14D,H14E,H14F), C13(H13D,
 H13E,H13F), C16(H16A,H16B,H16C)
2.d Idealised tetrahedral OH refined as rotating group:
 O3(H3), O7(H7)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.361
_oxdiff_exptl_absorpt_empirical_full_min 0.714