Chloraserrtone A, a Sesquiterpenoid Dimer from Chloranthus serratus.
Bai, Bai; Ye, Shao-Xia; Yang, De-Po; Zhu, Long-Ping; Tang, Gui-Hua; Chen, Yun-Yun; Li, George Qian; Zhao, Zhi-Min; Journal of natural products 82 (2019) 407–411; doi:10.1021/acs.jnatprod.8b00418

data_1552643
_publ_section_title
;
 Chloraserrtone A, a Sesquiterpenoid Dimer from Chloranthus serratus.
;
_journal_issue                   2
_journal_name_full               'Journal of natural products'
_journal_page_first              407
_journal_page_last               411
_journal_paper_doi               10.1021/acs.jnatprod.8b00418
_journal_volume                  82
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C32 H36 O9'
_chemical_formula_sum            'C32 H36 O9'
_chemical_formula_weight         564.61
_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             2018-04-09
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.07035(13)
_cell_length_b                   12.6890(2)
_cell_length_c                   21.8340(4)
_cell_measurement_reflns_used    10131
_cell_measurement_temperature    100
_cell_measurement_theta_max      75.7440
_cell_measurement_theta_min      4.0080
_cell_volume                     2790.01(8)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41r (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41r (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41r (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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      100
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.2417
_diffrn_detector_type            Onyx
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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   -124.00  36.00   1.00    6.00    --  -44.06   0.00  60.00  160
  2  \w      2.00  97.00   1.00    6.00    --   44.06-125.00 -30.00   95
  3  \w     25.00 109.00   1.00   25.00    --  108.00 -94.00 120.00   84
  4  \w     35.00 135.00   1.00   25.00    --  108.00 -30.00 150.00  100
  5  \w     38.00 135.00   1.00   25.00    --  108.00 -61.00 -90.00   97
  6  \w     29.00 147.00   1.00   25.00    --  108.00 -15.00-120.00  118
  7  \w     73.00 178.00   1.00   25.00    --  108.00 125.00   0.00  105
  8  \w     81.00 178.00   1.00   25.00    --  108.00  30.00  60.00   97
  9  \w     34.00 121.00   1.00   25.00    --  108.00-125.00  90.00   87
 10  \w     25.00 109.00   1.00   25.00    --  108.00 -94.00 -90.00   84
 11  \w   -125.00 -79.00   1.00    6.00    --  -44.06 -99.00 -60.00   46
 12  \w     18.00 114.00   1.00    6.00    --   44.06  57.00 -30.00   96
 13  \w     73.00 118.00   1.00    6.00    --   44.06 125.00 -60.00   45
 14  \w     76.00 115.00   1.00   25.00    --  108.00  77.00 -30.00   39
 15  \w     81.00 178.00   1.00   25.00    --  108.00  30.00-120.00   97
 16  \w     69.00 178.00   1.00   25.00    --  108.00  15.00 -30.00  109
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Onyx, Nova'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0590036000
_diffrn_orient_matrix_UB_12      0.0913783000
_diffrn_orient_matrix_UB_13      0.0377107000
_diffrn_orient_matrix_UB_21      -0.1410396000
_diffrn_orient_matrix_UB_22      0.0400503000
_diffrn_orient_matrix_UB_23      0.0141996000
_diffrn_orient_matrix_UB_31      -0.0038237000
_diffrn_orient_matrix_UB_32      -0.0692363000
_diffrn_orient_matrix_UB_33      0.0579247000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.1029
_diffrn_reflns_av_unetI/netI     0.0665
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            26858
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.126
_diffrn_reflns_theta_min         4.029
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Nova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.808
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.18397
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41r (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    1.344
_exptl_crystal_description       block
_exptl_crystal_F_000             1200
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.242
_refine_diff_density_min         -0.196
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details
;
 Flack x determined using 1846 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.07(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     411
_refine_ls_number_reflns         5516
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.0549
_refine_ls_R_factor_gt           0.0481
_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^)+(0.0572P)^2^+0.2605P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1184
_refine_ls_wR_factor_ref         0.1262
_reflns_Friedel_coverage         0.769
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                4917
_reflns_number_total             5516
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np8b00418_si_002.cif
_cod_data_source_block           bb_180129_2
_cod_original_cell_volume        2790.00(8)
_cod_database_code               1552643
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.924
_shelx_estimated_absorpt_t_min   0.794
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     71.98
_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. Uiso/Uaniso restraints and constraints
Uanis(C3) = Uanis(C3A)
3. Others
 Sof(C3A)=Sof(O1A)=Sof(C0AB)=Sof(H0AE)=Sof(H0AF)=Sof(H0AG)=Sof(O2A)=1-FVAR(1)
 Sof(O1)=Sof(O2)=Sof(C3)=Sof(C0AA)=Sof(H0AB)=Sof(H0AC)=Sof(H0AD)=FVAR(1)
4.a Ternary CH refined with riding coordinates:
 C15(H15), C16(H16), C19(H19), C28(H28), C29(H29), C30(H30), C32(H32)
4.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C26(H26A,H26B), C33(H33A,H33B), C36(H36A,H36B)
4.c Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C), C24(H24A,H24B,H24C), C34(H34A,H34B,H34C), C37(H37A,H37B,
 H37C), C38(H38A,H38B,H38C), C0AA(H0AB,H0AC,H0AD), C0AB(H0AE,H0AF,H0AG)
4.d Idealised tetrahedral OH refined as rotating group:
 O1AA(H1AA), O0AA(H0AA), O3(H3)
;
_shelx_res_checksum              70144
_shelx_hkl_checksum              6163
_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
;
_oxdiff_exptl_absorpt_empirical_full_max 4.982
_oxdiff_exptl_absorpt_empirical_full_min 0.426