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_1558528
_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         'C19 H26 O3, 0.5(C H4 O)'
_chemical_formula_sum            'C19.5 H28 O3.5'
_chemical_formula_weight         318.42
_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     dual
_audit_creation_date             2017-12-25
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   6.7321(3)
_cell_length_b                   13.4089(6)
_cell_length_c                   37.6911(17)
_cell_measurement_reflns_used    7457
_cell_measurement_temperature    296
_cell_measurement_theta_max      53.597
_cell_measurement_theta_min      7.696
_cell_volume                     3402.4(3)
_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      296
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.995
_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  0.0371
_diffrn_reflns_av_unetI/netI     0.0260
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       45
_diffrn_reflns_limit_l_min       -45
_diffrn_reflns_number            32055
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         54.823
_diffrn_reflns_theta_min         3.043
_exptl_absorpt_coefficient_mu    0.429
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.6133
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0901 before and 0.0500 after correction. The Ratio of minimum to maximum transmission is 0.7952. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.243
_exptl_crystal_description       prism
_exptl_crystal_F_000             1384
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.168
_refine_diff_density_min         -0.327
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details
;
 Flack x determined using 2120 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.06(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     420
_refine_ls_number_reflns         6427
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.079
_refine_ls_R_factor_all          0.0544
_refine_ls_R_factor_gt           0.0461
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0770P)^2^+0.3752P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1247
_refine_ls_wR_factor_ref         0.1347
_reflns_Friedel_coverage         0.740
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.994
_reflns_number_gt                5593
_reflns_number_total             6427
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np0c00064_si_002.cif
_cod_data_source_block           mjr17096_0m
_cod_depositor_comments
'Adding full bibliography for 1558526--1558528.cif.'
_cod_original_formula_sum        'C19.50 H28 O3.50'
_cod_database_code               1558528
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_max   0.996
_shelx_estimated_absorpt_t_min   0.950
_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.a Ternary CH refined with riding coordinates:
 C3(H3), C5(H5), C9(H9), C13(H13), C3A(H3A), C5A(H5A), C9A(H9A), C13A(H13A)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C6(H6A,H6B), C7(H7A,H7B), C11(H11A,H11B), C12(H12A,
 H12B), C14(H14A,H14B), C18(H18A,H18B), C1A(H1AB,H1AC), C2A(H2AA,H2AB),
 C6A(H6AA,H6AB), C7A(H7AA,H7AB), C11A(H11C,H11D), C12A(H12C,H12D), C14A(H14C,
 H14D), C18A(H18C,H18D)
2.c Tetrahedral OH refined with riding coordinates:
 O1S(H1S)
2.d X=CH2 refined with riding coordinates:
 C17(H17A,H17B), C17A(H17C,H17D)
2.e Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C20A(H20D,H20E,H20F), C1S(H1SA,H1SB,H1SC)
2.f Idealised tetrahedral OH refined as rotating group:
 O1(H1), O1A(H1AA)
;
_shelx_res_checksum              44881
_shelx_hkl_checksum              19675
_olex2_submission_special_instructions 'No special instructions were received'