Diverse Chemosensitizing 8,9-Secolindenane-Type Sesquiterpenoid Oligomers and Monomers from <i>Sarcandra glabra</i>.
Chi, Jun; Wei, Shanshan; Gao, Hongliang; Xu, Dingqiao; Zhang, Lina; Yang, Lei; Xu, Wenjun; Luo, Jun; Kong, Lingyi; The Journal of organic chemistry 84 (2019) 9117–9126; doi:10.1021/acs.joc.9b00986

data_4034163
_publ_section_title
;
 Diverse Chemosensitizing 8,9-Secolindenane-Type Sesquiterpenoid Oligomers
 and Monomers from <i>Sarcandra glabra</i>.
;
_journal_issue                   14
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              9117
_journal_page_last               9126
_journal_paper_doi               10.1021/acs.joc.9b00986
_journal_volume                  84
_journal_year                    2019
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C32 H38 O8'
_chemical_formula_sum            'C32 H38 O8'
_chemical_formula_weight         550.62
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2019-04-17
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 91.743(14)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.510(5)
_cell_length_b                   35.163(11)
_cell_length_c                   10.914(3)
_cell_measurement_reflns_used    251
_cell_measurement_temperature    220
_cell_measurement_theta_max      63.63
_cell_measurement_theta_min      38.99
_cell_volume                     2881(2)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      220
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.952
_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  0.0685
_diffrn_reflns_av_unetI/netI     0.0636
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.952
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       41
_diffrn_reflns_limit_k_min       -41
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            37278
_diffrn_reflns_point_group_measured_fraction_full 0.936
_diffrn_reflns_point_group_measured_fraction_max 0.892
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         71.086
_diffrn_reflns_theta_min         2.513
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.741
_exptl_absorpt_correction_T_max  0.7534
_exptl_absorpt_correction_T_min  0.6374
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1770 before and 0.0670 after correction.
The Ratio of minimum to maximum transmission is 0.8460.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.270
_exptl_crystal_description       block
_exptl_crystal_F_000             1176
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.193
_refine_diff_density_min         -0.241
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details
;
 Flack x determined using 2865 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.15(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     752
_refine_ls_number_reflns         9954
_refine_ls_number_restraints     867
_refine_ls_restrained_S_all      1.015
_refine_ls_R_factor_all          0.0684
_refine_ls_R_factor_gt           0.0473
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0556P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1044
_refine_ls_wR_factor_ref         0.1157
_reflns_Friedel_coverage         0.841
_reflns_Friedel_fraction_full    0.879
_reflns_Friedel_fraction_max     0.830
_reflns_number_gt                7701
_reflns_number_total             9954
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b00986_si_002.cif
_cod_data_source_block           compound_6
_cod_database_code               4034163
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.964
_shelx_estimated_absorpt_t_min   0.872
_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
2. Restrained distances
 O9-C18B \\sim O1-C12A
 with sigma of 0.02
 O9-C16B \\sim O9-C18B \\sim C17B-C16B \\sim C19B-C18B
 with sigma of 0.02
3. Rigid bond restraints
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within 2A with sigma of 0.04 and sigma
for terminal atoms of 0.08
Uanis(C13B) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01
5. Others
 Fixed Sof: C18B(0.5) H18A(0.5) H18B(0.5) C19B(0.5) H19A(0.5) H19B(0.5)
 H19C(0.5) C16B(0.5) H16A(0.5) H16B(0.5) C17B(0.5) H17C(0.5) H17D(0.5) H17E(0.5)
6.a Ternary CH refined with riding coordinates:
 C9(H9), C5A(H5A), C9A(H9A), C5(H5), C1A(H1A), C9B(H9B), C1(H1), C18(H18),
 C24(H24), C16(H16), C20(H20), C5B(H5B), C3(H3), C3A(H3A), C3B(H3B), C1B(H1B)
6.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C6A(H6AA,H6AB), C21(H21A,H21B), C2B(H2BA,H2BB), C16A(H16C,H16D),
 C6B(H6BA,H6BB), C2(H2A,H2B), C2A(H2AA,H2AB), C17(H17A,H17B), C18B(H18A,H18B),
 C16B(H16A,H16B)
6.c X=CH2 refined with riding coordinates:
 C30(H30A,H30B), C15(H15G,H15H)
6.d Idealised Me refined as rotating group:
 C14(H14D,H14E,H14F), C15A(H15D,H15E,H15F), C29(H29A,H29B,H29C), C15B(H15A,
 H15B,H15C), C14A(H14G,H14H,H14I), C14B(H14A,H14B,H14C), C28(H28A,H28B,H28C),
 C13(H13D,H13E,H13F), C13A(H13G,H13H,H13I), C17A(H17F,H17G,H17H), C13B(H13A,
 H13B,H13C), C19B(H19A,H19B,H19C), C17B(H17C,H17D,H17E)
;
_olex2_submission_special_instructions 'No special instructions were received'