Ciliatonoids A and B, Two Limonoids from Toona ciliata.
Liu, Cui-Ping; Wang, Guo-Cai; Gan, Li-She; Xu, Cheng-Hui; Liu, Qun-Fang; Ding, Jian; Yue, Jian-Min; Organic letters 18 (2016) 2894–2897; doi:10.1021/acs.orglett.6b01213

data_1543829
_publ_section_title
;
 Ciliatonoids A and B, Two Limonoids from Toona ciliata.
;
_journal_issue                   12
_journal_name_full               'Organic letters'
_journal_page_first              2894
_journal_page_last               2897
_journal_paper_doi               10.1021/acs.orglett.6b01213
_journal_volume                  18
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_formula_sum            'C26 H32 O5'
_chemical_formula_weight         424.51
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_symmetry_space_group_name_Hall  'P 1'
_symmetry_space_group_name_H-M   'P 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                114.2120(10)
_cell_angle_beta                 90.2770(10)
_cell_angle_gamma                91.3950(10)
_cell_formula_units_Z            2
_cell_length_a                   7.2748(2)
_cell_length_b                   12.3230(3)
_cell_length_c                   13.1676(3)
_cell_measurement_reflns_used    5179
_cell_measurement_temperature    140(2)
_cell_measurement_theta_max      69.69
_cell_measurement_theta_min      3.68
_cell_volume                     1076.14(5)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      140(2)
_diffrn_measured_fraction_theta_full 0.950
_diffrn_measured_fraction_theta_max 0.929
_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  0.0416
_diffrn_reflns_av_unetI/netI     0.0680
_diffrn_reflns_Laue_measured_fraction_full 0.950
_diffrn_reflns_Laue_measured_fraction_max 0.929
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            8863
_diffrn_reflns_point_group_measured_fraction_full 0.679
_diffrn_reflns_point_group_measured_fraction_max 0.661
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         69.807
_diffrn_reflns_theta_min         3.681
_exptl_absorpt_coefficient_mu    0.721
_exptl_absorpt_correction_T_max  0.7533
_exptl_absorpt_correction_T_min  0.5520
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.310
_exptl_crystal_description       blocks
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.060
_refine_diff_density_max         0.583
_refine_diff_density_min         -0.409
_refine_diff_density_rms         0.107
_refine_ls_abs_structure_details
; 
 Flack x determined using 1462 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.14(19)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     569
_refine_ls_number_reflns         5362
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.0648
_refine_ls_R_factor_gt           0.0628
_refine_ls_shift/su_max          0.019
_refine_ls_shift/su_mean         0.003
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1400P)^2^+0.1174P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1622
_refine_ls_wR_factor_ref         0.1693
_reflns_Friedel_coverage         0.423
_reflns_Friedel_fraction_full    0.408
_reflns_Friedel_fraction_max     0.392
_reflns_number_gt                5188
_reflns_number_total             5362
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol6b01213_si_002.cif
_cod_data_source_block           cu_dm14221_0m
_cod_database_code               1543829
_shelx_estimated_absorpt_t_min   0.813
_shelx_estimated_absorpt_t_max   0.958
_shelxl_version_number           2013-4
_shelx_res_checksum              68759
_shelx_hkl_checksum              56806