Taiwanoids A-D, four dimeric diterpenoids featuring tetracyclic [7. 7<sup>5, 9</sup>. 4. 0<sup>5, 10</sup>. 0<sup>8, 9</sup>] octodecane from Taiwania cryptomerioidesim.
Wang, Wen-Li; Zhu, Dong-Rong; Luo, Jie; Liu, Fei-Yan; Chen, Chen; Zhu, Tian-Yu; Li, Ling-Nan; Han, Chao; Luo, Jian-Guang; Kong, Ling-Yi; Organic & biomolecular chemistry 16 (2018) 9059–9063; doi:10.1039/c8ob02566e

data_7156564
_publ_section_title
;
 Taiwanoids A-D, four dimeric diterpenoids featuring tetracyclic [7.
 7<sup>5, 9</sup>. 4. 0<sup>5, 10</sup>. 0<sup>8, 9</sup>] octodecane from
 Taiwania cryptomerioidesim.
;
_journal_issue                   46
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              9059
_journal_page_last               9063
_journal_paper_doi               10.1039/c8ob02566e
_journal_volume                  16
_journal_year                    2018
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C41 H58 O7'
_chemical_formula_sum            'C41 H58 O7'
_chemical_formula_weight         662.87
_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'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-04-14
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2018-08-17 deposited with the CCDC.
2018-11-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   12.9237(4)
_cell_length_b                   15.5472(4)
_cell_length_c                   39.6257(12)
_cell_measurement_reflns_used    9770
_cell_measurement_temperature    173
_cell_measurement_theta_max      74.39
_cell_measurement_theta_min      3.61
_cell_volume                     7961.9(4)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 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      173.0
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_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  0.0827
_diffrn_reflns_av_unetI/netI     0.0358
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       49
_diffrn_reflns_limit_l_min       -49
_diffrn_reflns_number            128664
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         74.490
_diffrn_reflns_theta_min         3.053
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.588
_exptl_absorpt_correction_T_max  0.7538
_exptl_absorpt_correction_T_min  0.5797
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1188 before and 0.0782 after correction. The Ratio of minimum to maximum transmission is 0.7690. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.106
_exptl_crystal_description       block
_exptl_crystal_F_000             2880
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_platon_squeeze_details
;
TITL 180411YWS_ZZY_0ma_a.res in P2(1)2(1)2(1)
CELL   12.9237   15.5472   39.6257     90.00     90.00     90.00
SPGR P212121
Q101 0.700 0.052 0.680 !       5.94 eA-3
C102 0.840 0.979 0.217 !       1.51 eA-3
C103 0.610 0.062 0.650 !       1.19 eA-3
C104 0.218 0.490 0.241 !       1.18 eA-3
C105 0.042 0.398 0.250 !       0.88 eA-3
C106 0.391 0.547 0.734 !       0.75 eA-3
C107 0.888 0.963 0.296 !       0.73 eA-3
C108 0.420 0.559 0.710 !       0.56 eA-3
C109 0.424 0.552 0.783 !       0.56 eA-3
;
_refine_diff_density_max         0.179
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details
;
 Flack x determined using 5621 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.08(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     897
_refine_ls_number_reflns         16273
_refine_ls_number_restraints     43
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0536
_refine_ls_R_factor_gt           0.0439
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0718P)^2^+0.7140P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1118
_refine_ls_wR_factor_ref         0.1185
_reflns_Friedel_coverage         0.821
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                14026
_reflns_number_total             16273
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8ob02566e2.cif
_cod_data_source_block           180411yws_zzy_0ma_a_sq
_cod_depositor_comments          'Adding full bibliography for 7156564.cif.'
_cod_database_code               7156564
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.933
_shelx_estimated_absorpt_t_min   0.853
_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. Restrained distances
 C36-C34 \\sim C37-C34
 with sigma of 0.02
 C37-C34 \\sim C36-C34
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C37) \\sim Ueq, Uanis(C36) \\sim Ueq: with sigma of 0.005 and sigma for
terminal atoms of 0.01
Uanis(C35) \\sim Ueq: with sigma of 0.05 and sigma for terminal atoms of 0.1
4. Others
 Fixed Sof: H34(0.68) H34A(0.32) C36(0.68) H36C(0.68) H36D(0.68) H36E(0.68)
 C37(0.32) H37A(0.32) H37B(0.32) H37C(0.32)
5.a Ternary CH refined with riding coordinates:
 C25(H25), C26'(H26'), C27(H27), C30'(H30'), C33'(H33'), C34(H34), C34(H34A),
 C5'(H5'), C5(H5), C7(H7), C9'(H9'), C12'(H12'), C15(H15)
5.b Secondary CH2 refined with riding coordinates:
 C21(H21A,H21B), C22(H22A,H22B), C22'(H22C,H22D), C23'(H23A,H23B), C23(H23C,
 H23D), C24'(H24A,H24B), C27'(H27A,H27B), C28'(H28A,H28B), C32'(H32A,H32B),
 C36'(H36A,H36B), C1(H1A,H1B), C1'(H1'A,H1'B), C2(H2A,H2B), C2'(H2'A,H2'B),
 C3(H3A,H3B), C3'(H3'A,H3'B), C6'(H6'A,H6'B), C7'(H7'A,H7'B), C11'(H11A,H11B),
 C15'(H15A,H15B)
5.c Aromatic/amide H refined with riding coordinates:
 C35'(H35'), C14'(H14')
5.d X=CH2 refined with riding coordinates:
 C39'(H39A,H39B), C17'(H17D,H17E)
5.e Idealised Me refined as rotating group:
 C1H(H1HA,H1HB,H1HC), C1C(H1CA,H1CB,H1CC), C20A(H20A,H20B,H20C), C35(H35A,H35B,
 H35C), C36(H36C,H36D,H36E), C37(H37A,H37B,H37C), C37'(H37D,H37E,H37F),
 C38'(H38A,H38B,H38C), C40'(H40A,H40B,H40C), C42'(H42A,H42B,H42C), C16(H16A,
 H16B,H16C), C16'(H16D,H16E,H16F), C17(H17A,H17B,H17C), C18(H18A,H18B,H18C),
 C21'(H21C,H21D,H21E), C19'(H19A,H19B,H19C), C19(H19D,H19E,H19F), C20'(H20D,
 H20E,H20F), C20(H20G,H20H,H20I)
5.f Idealised tetrahedral OH refined as rotating group:
 O4A(H4A), O6A(H6A), O2(H2), O4(H4)
;
_platon_squeeze_void_probe_radius 1.20
_olex2_submission_special_instructions 'No special instructions were received'