Taicrypnacids A and B, a Pair of C<sub>37</sub> Heterodimeric Diterpenoid Stereoisomers from <i>Taiwania cryptomerioides</i>.
Wang, Wen-Li; Zhu, Dong-Rong; Chen, Chen; Zhu, Tian-Yu; Han, Chao; Liu, Fei-Yan; Li, Ling-Nan; Luo, Jian-Guang; Kong, Ling-Yi; Journal of natural products 82 (2019) 2087–2093; doi:10.1021/acs.jnatprod.8b00815

data_1552607
_publ_section_title
;
 Taicrypnacids A and B, a Pair of C<sub>37</sub> Heterodimeric Diterpenoid
 Stereoisomers from <i>Taiwania cryptomerioides</i>.
;
_journal_issue                   8
_journal_name_full               'Journal of natural products'
_journal_page_first              2087
_journal_page_last               2093
_journal_paper_doi               10.1021/acs.jnatprod.8b00815
_journal_volume                  82
_journal_year                    2019
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C38 H54 O4'
_chemical_formula_sum            'C38 H54 O4'
_chemical_formula_weight         574.81
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2018-04-30
_audit_creation_method
;
Olex2 1.2
(compiled 2018.04.26 svn.r3504 for OlexSys, GUI svn.r5492)
;
_cell_angle_alpha                90
_cell_angle_beta                 91.587(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.5430(2)
_cell_length_b                   11.3039(3)
_cell_length_c                   19.2193(6)
_cell_measurement_reflns_used    7484
_cell_measurement_temperature    173
_cell_measurement_theta_max      69.570
_cell_measurement_theta_min      2.300
_cell_volume                     1638.11(8)
_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 (Sheldrick, 2015)'
_diffrn_ambient_temperature      173.0
_diffrn_measured_fraction_theta_full 0.967
_diffrn_measured_fraction_theta_max 0.967
_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  0.0396
_diffrn_reflns_av_unetI/netI     0.0326
_diffrn_reflns_Laue_measured_fraction_full 0.967
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            18347
_diffrn_reflns_point_group_measured_fraction_full 0.918
_diffrn_reflns_point_group_measured_fraction_max 0.918
_diffrn_reflns_theta_full        65.990
_diffrn_reflns_theta_max         65.990
_diffrn_reflns_theta_min         2.300
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.570
_exptl_absorpt_correction_T_max  0.7534
_exptl_absorpt_correction_T_min  0.6851
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0735 before and 0.0554 after correction. The Ratio of minimum to maximum transmission is 0.9093. The \l/2 correction factor is 0.00150.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.165
_exptl_crystal_description       needle
_exptl_crystal_F_000             628
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.116
_refine_diff_density_min         -0.130
_refine_diff_density_rms         0.027
_refine_ls_abs_structure_details
;
 Flack x determined using 2020 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.16(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     390
_refine_ls_number_reflns         5224
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0353
_refine_ls_R_factor_gt           0.0317
_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^)+(0.0473P)^2^+0.0465P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0789
_refine_ls_wR_factor_ref         0.0808
_reflns_Friedel_coverage         0.800
_reflns_Friedel_fraction_full    0.864
_reflns_Friedel_fraction_max     0.864
_reflns_number_gt                4824
_reflns_number_total             5224
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np8b00815_si_002.cif
_cod_data_source_block           cu_20180421-ysh-2_0m
_cod_database_code               1552607
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.983
_shelx_estimated_absorpt_t_min   0.935
_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
 O1-H1
 0.84 with sigma of 0.02
3.a Ternary CH refined with riding coordinates:
 C5(H5), C5'(H5'), C7(H7), C9'(H9'), C14'(H14')
3.b Secondary CH2 refined with riding coordinates:
 C1'(H1'A,H1'B), C1(H1A,H1B), C2(H2A,H2B), C2'(H2'A,H2'B), C3'(H3'A,H3'B),
 C3(H3A,H3B), C6'(H6'A,H6'B), C6(H6A,H6B), C7'(H7'A,H7'B), C11'(H11A,H11B),
 C15'(H15A,H15B)
3.c Aromatic/amide H refined with riding coordinates:
 C11(H11), C12'(H12'), C12(H12)
3.d X=CH2 refined with riding coordinates:
 C17'(H17A,H17B)
3.e Idealised Me refined as rotating group:
 C16'(H16A,H16B,H16C), C18(H18A,H18B,H18C), C19(H19A,H19B,H19C), C19'(H19D,
 H19E,H19F), C20'(H20A,H20B,H20C), C20(H20D,H20E,H20F), C21'(H21A,H21B,H21C)
;
_olex2_submission_special_instructions 'No special instructions were received'