Cipacinoids A-D, Four Limonoids with Spirocyclic Skeletons from Cipadessa cinerascens.
Yu, Jin-Hai; Liu, Qun-Fang; Sheng, Li; Wang, Guo-Cai; Li, Jia; Yue, Jian-Min; Organic letters 18 (2016) 444–447; doi:10.1021/acs.orglett.5b03487

data_1542268
_publ_section_title
;
 Cipacinoids A-D, Four Limonoids with Spirocyclic Skeletons from Cipadessa
 cinerascens.
;
_journal_issue                   3
_journal_name_full               'Organic letters'
_journal_page_first              444
_journal_page_last               447
_journal_paper_doi               10.1021/acs.orglett.5b03487
_journal_volume                  18
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_formula_sum            'C29 H40 O10'
_chemical_formula_weight         548.61
_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'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 90.9090(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.30560(10)
_cell_length_b                   28.5217(5)
_cell_length_c                   12.1649(2)
_cell_measurement_reflns_used    9953
_cell_measurement_temperature    140(2)
_cell_measurement_theta_max      68.77
_cell_measurement_theta_min      3.10
_cell_volume                     2881.38(8)
_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 0.995
_diffrn_measured_fraction_theta_max 0.977
_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  0.0293
_diffrn_reflns_av_unetI/netI     0.0366
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            20674
_diffrn_reflns_point_group_measured_fraction_full 0.861
_diffrn_reflns_point_group_measured_fraction_max 0.840
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         69.640
_diffrn_reflns_theta_min         3.099
_exptl_absorpt_coefficient_mu    0.788
_exptl_absorpt_correction_T_max  0.7533
_exptl_absorpt_correction_T_min  0.5794
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.265
_exptl_crystal_description       plate
_exptl_crystal_F_000             1176
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.030
_refine_diff_density_max         0.563
_refine_diff_density_min         -0.241
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details
; 
 Flack x determined using 3467 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   -0.01(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     723
_refine_ls_number_reflns         9095
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.014
_refine_ls_R_factor_all          0.0370
_refine_ls_R_factor_gt           0.0360
_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^)+(0.0637P)^2^+0.3951P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0963
_refine_ls_wR_factor_ref         0.0975
_reflns_Friedel_coverage         0.684
_reflns_Friedel_fraction_full    0.722
_reflns_Friedel_fraction_max     0.697
_reflns_number_gt                8838
_reflns_number_total             9095
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol5b03487_si_002.cif
_cod_data_source_block           cu_dm13428_0m
_cod_depositor_comments
'Adding full bibliography for 1542268--1542269.cif.'
_cod_database_code               1542268
_shelx_estimated_absorpt_t_min   0.858
_shelx_estimated_absorpt_t_max   0.977
_shelxl_version_number           2013-4
_shelx_res_checksum              29753
_shelx_hkl_checksum              16154