Amentotaxins C-V, Structurally Diverse Diterpenoids from the Leaves and Twigs of the Vulnerable Conifer <i>Amentotaxus argotaenia</i> and Their Cytotoxic Effects.
Li, Hao; Liang, Yu-Ru; Chen, Shao-Xin; Wang, Wen-Xuan; Zou, Yike; Nuryyeva, Selbi; Houk, K. N.; Xiong, Juan; Hu, Jin-Feng; Journal of natural products 83 (2020) 2129–2144; doi:10.1021/acs.jnatprod.0c00064

data_1558527
_publ_section_title
;
 Amentotaxins C-V, Structurally Diverse Diterpenoids from the Leaves and
 Twigs of the Vulnerable Conifer <i>Amentotaxus argotaenia</i> and Their
 Cytotoxic Effects.
;
_journal_issue                   7
_journal_name_full               'Journal of natural products'
_journal_page_first              2129
_journal_page_last               2144
_journal_paper_doi               10.1021/acs.jnatprod.0c00064
_journal_volume                  83
_journal_year                    2020
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C20 H32 O3, 0.5(H2 O)'
_chemical_formula_sum            'C20 H33 O3.5'
_chemical_formula_weight         329.46
_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     dual
_audit_creation_date             2019-04-18
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            16
_cell_length_a                   7.6538(3)
_cell_length_b                   22.4697(10)
_cell_length_c                   44.905(2)
_cell_measurement_reflns_used    9885
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      53.80
_cell_measurement_theta_min      3.42
_cell_volume                     7722.7(6)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 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_temperature      170.02
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.1319
_diffrn_reflns_av_unetI/netI     0.1236
_diffrn_reflns_Laue_measured_fraction_full 0.978
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       54
_diffrn_reflns_limit_l_min       -53
_diffrn_reflns_number            77265
_diffrn_reflns_point_group_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         55.109
_diffrn_reflns_theta_min         3.086
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.384
_exptl_absorpt_correction_T_max  0.6967
_exptl_absorpt_correction_T_min  0.5350
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1640 before and 0.1166 after correction. The Ratio of minimum to maximum transmission is 0.7679. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.133
_exptl_crystal_description       prism
_exptl_crystal_F_000             2896
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.01
_exptl_crystal_size_min          0.005
_refine_diff_density_max         0.446
_refine_diff_density_min         -0.309
_refine_diff_density_rms         0.075
_refine_ls_abs_structure_details
;
 Flack x determined using 2690 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.02(17)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.993
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     880
_refine_ls_number_reflns         14481
_refine_ls_number_restraints     53
_refine_ls_restrained_S_all      8.597
_refine_ls_R_factor_all          0.1498
_refine_ls_R_factor_gt           0.1107
_refine_ls_shift/su_max          0.021
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0500P)^2^+20.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2428
_refine_ls_wR_factor_ref         0.2662
_reflns_Friedel_coverage         0.793
_reflns_Friedel_fraction_full    0.986
_reflns_Friedel_fraction_max     0.981
_reflns_number_gt                9370
_reflns_number_total             14481
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np0c00064_si_004.cif
_cod_data_source_block           mj19230_0m
_cod_depositor_comments
'Adding full bibliography for 1558526--1558528.cif.'
_cod_original_cell_volume        7722.6(6)
_cod_original_formula_sum        'C20 H33 O3.50'
_cod_database_code               1558527
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.998
_shelx_estimated_absorpt_t_min   0.981
_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, All O(H,H) groups
2. Restrained distances
 C16B-C15B
 1.36 with sigma of 0.02
 C13B-C15B
 1.5 with sigma of 0.02
 C16B-C13B
 2.2 with sigma of 0.02
 C16-C15
 1.36 with sigma of 0.02
 H1-H2B_$1
 2 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
C13B \\sim C15B \\sim C16B: within 2A with sigma of 0.01 and sigma for terminal
atoms of 0.02
C11B \\sim C12B \\sim C13B \\sim C14B \\sim C15B \\sim C16B \\sim C17B: within
2A with sigma of 0.01 and sigma for terminal atoms of 0.02
C13 \\sim C15 \\sim C16: within 2A with sigma of 0.01 and sigma for terminal
atoms of 0.02
4.a Free rotating group:
 O1S(H1SA,H1SB), O2S(H2SA,H2SB)
4.b Ternary CH refined with riding coordinates:
 C2(H2A), C3(H3A), C5(H5), C9(H9), C2A(H2AB), C3A(H3AB), C5A(H5A), C9A(H9A),
 C2B(H2BA), C3B(H3BA), C5B(H5B), C9B(H9B), C2C(H2CA), C3C(H3CA), C5C(H5C),
 C9C(H9C)
4.c Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C6(H6A,H6B), C7(H7A,H7B), C11(H11A,H11B), C12(H12A,H12B),
 C18(H18A,H18B), C1A(H1AB,H1AC), C6A(H6AA,H6AB), C7A(H7AA,H7AB), C11A(H11C,
 H11D), C12A(H12C,H12D), C18A(H18C,H18D), C1B(H1BB,H1BC), C6B(H6BA,H6BB),
 C7B(H7BA,H7BB), C11B(H11E,H11F), C12B(H12E,H12F), C18B(H18E,H18F), C1C(H1CA,
 H1CB), C6C(H6CA,H6CB), C7C(H7CA,H7CB), C11C(H11G,H11H), C12C(H12G,H12H),
 C18C(H18G,H18H)
4.d Aromatic/amide H refined with riding coordinates:
 C14(H14), C15(H15), C14A(H14A), C15A(H15A), C14B(H14B), C15B(H15B),
 C14C(H14C), C15C(H15C)
4.e Tetrahedral OH refined with riding coordinates:
 O2A(H2AA), O2B(H2B), O2C(H2C)
4.f X=CH2 refined with riding coordinates:
 C16(H16A,H16B), C16A(H16C,H16D), C16B(H16E,H16F), C16C(H16G,H16H)
4.g Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C19(H19A,H19B,H19C), C20(H20A,H20B,H20C), C17A(H17D,H17E,
 H17F), C19A(H19D,H19E,H19F), C20A(H20D,H20E,H20F), C17B(H17G,H17H,H17I),
 C19B(H19G,H19H,H19I), C20B(H20G,H20H,H20I), C17C(H17J,H17K,H17L), C19C(H19J,
 H19K,H19L), C20C(H20J,H20K,H20L)
4.h Idealised tetrahedral OH refined as rotating group:
 O1(H1), O3(H3), O3A(H3AA), O1B(H1BA), O3B(H3B), O1C(H1C), O3C(H3C)
;
_shelx_res_checksum              54209
_shelx_hkl_checksum              54658
_shelx_fab_checksum              93277
_olex2_submission_special_instructions 'No special instructions were received'