Ainsliatriolides A and B, Two Guaianolide Trimers from Ainsliaea fragrans and Their Cytotoxic Activities.
Zhang, Rui; Tang, Chunping; Liu, Hong-Chun; Ren, Yongmei; Xu, Cheng-Hui; Ke, Chang-Qiang; Yao, Sheng; Huang, Xun; Ye, Yang; The Journal of organic chemistry 83 (2018) 14175–14180; doi:10.1021/acs.joc.8b02346

data_4034864
_publ_section_title
;
 Ainsliatriolides A and B, Two Guaianolide Trimers from Ainsliaea fragrans
 and Their Cytotoxic Activities.
;
_journal_issue                   22
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              14175
_journal_page_last               14180
_journal_paper_doi               10.1021/acs.joc.8b02346
_journal_volume                  83
_journal_year                    2018
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C45 H48 O12, H2 O'
_chemical_formula_sum            'C45 H50 O13'
_chemical_formula_weight         798.85
_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             2018-05-15
_audit_creation_method
;
Olex2 1.2
(compiled 2018.04.26 svn.r3504 for OlexSys, GUI svn.r5492)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.8145(14)
_cell_length_b                   15.5156(15)
_cell_length_c                   19.1787(19)
_cell_measurement_reflns_used    7374
_cell_measurement_temperature    205
_cell_measurement_theta_max      65.34
_cell_measurement_theta_min      3.66
_cell_volume                     4408.3(7)
_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      205.0
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.981
_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  0.0480
_diffrn_reflns_av_unetI/netI     0.0359
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            33811
_diffrn_reflns_point_group_measured_fraction_full 0.975
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        66.495
_diffrn_reflns_theta_max         66.495
_diffrn_reflns_theta_min         3.664
_exptl_absorpt_coefficient_mu    0.729
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.6444
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0920 before and 0.0618 after correction. The Ratio of minimum to maximum transmission is 0.8560. The \l/2 correction factor is 0.00150.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.204
_exptl_crystal_description       block
_exptl_crystal_F_000             1696
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.11
_platon_squeeze_details          'TITL cu_2017863_0m_a.res in P2(1)2(1)2(1)'
_refine_diff_density_max         0.218
_refine_diff_density_min         -0.278
_refine_diff_density_rms         0.050
_refine_ls_abs_structure_details
;
 Flack x determined using 2845 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.17(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     532
_refine_ls_number_reflns         7574
_refine_ls_number_restraints     11
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0437
_refine_ls_R_factor_gt           0.0403
_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^)+(0.0838P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1147
_refine_ls_wR_factor_ref         0.1175
_reflns_Friedel_coverage         0.788
_reflns_Friedel_fraction_full    0.968
_reflns_Friedel_fraction_max     0.968
_reflns_number_gt                6966
_reflns_number_total             7574
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b02346_si_003.cif
_cod_data_source_block           cu_2017863_0m_sq_s_sq_s
_cod_database_code               4034864
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.924
_shelx_estimated_absorpt_t_min   0.822
_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 O(H) groups, All O(H,H) groups
2. Restrained distances
 H13G-H13H
 1.46 with sigma of 0.02
 O13-H13H = O13-H13G
 0.86 with sigma of 0.02
 O13-H13G
 0.7 with sigma of 0.02
 O10-O11 \\sim O10-C11B
 with sigma of 0.04
 C12B-O10 \\sim C12B-O11 \\sim C12B-C11B
 with sigma of 0.02
3.a Ternary CH refined with riding coordinates:
 C1(H1), C6(H6A), C5(H5), C5B(H5B), C7B(H7B), C6A(H6AA), C6B(H6B), C5A(H5A),
 C7A(H7A), C7(H7), C1B(H1B)
3.b Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C15A(H15C,H15D), C14A(H14A,H14B), C15B(H15E,H15F), C2(H2A,
 H2B), C2B(H2BA,H2BB), C9(H9A,H9B), C9A(H9AA,H9AB), C8B(H8BA,H8BB), C8A(H8AA,
 H8AB), C9B(H9BA,H9BB), C8(H8A,H8B)
3.c X=CH2 refined with riding coordinates:
 C14(H14C,H14D), C13A(H13A,H13B), C14B(H14E,H14F), C13(H13C,H13D), C13B(H13E,
 H13F)
3.d Idealised tetrahedral OH refined as rotating group:
 O6(H6), O3(H3), O9(H9)
;
_olex2_submission_special_instructions 'No special instructions were received'