Cytotoxic lignans from fruits of Cleistanthus indochinensis: synthesis of cleistantoxin derivatives.
Thanh, Van Trinh Thi; Pham, Van Cuong; Mai, Huong Doan Thi; Litaudon, Marc; Guéritte, Françoise; Retailleau, Pascal; Nguyen, Van Hung; Chau, Van Minh; Journal of natural products 75 (2012) 1578–1583; doi:10.1021/np3003832

data_1516055
_publ_section_title
;
 Cytotoxic lignans from fruits of Cleistanthus indochinensis: synthesis of
 cleistantoxin derivatives.
;
_journal_issue                   9
_journal_name_full               'Journal of natural products'
_journal_page_first              1578
_journal_page_last               1583
_journal_paper_doi               10.1021/np3003832
_journal_volume                  75
_journal_year                    2012
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C22 H18 O9, 0.5(C3 H6 O)'
_chemical_formula_sum            'C23.5 H21 O9.5'
_chemical_formula_weight         455.40
_chemical_name_systematic
; 
 (3aS,4R,5R,10bS)-5-(benzo[d][1,3]dioxol-5-yl)-10-methoxy-1-oxo-1,3,3a,4,5,10b-
hexahydrofuro[3',4':5,6]naphtho[2,3-d][1,3]dioxole-4-carboxylic acid compound
with propan-2-one (2:1)
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 92.481(12)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   10.876(3)
_cell_length_b                   6.7384(17)
_cell_length_c                   14.743(3)
_cell_measurement_reflns_used    164
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      68.3
_cell_measurement_theta_min      6.6
_cell_volume                     1079.5(5)
_computing_cell_refinement
'CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)'
_computing_data_collection
'CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)'
_computing_data_reduction
'CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)'
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement
'SHELXL97 (Sheldrick, 2008); CRYSTALBUILDER (Welter, 2006)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293
_diffrn_detector                 RX
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_details
;
scan:
    Number of images: 36
               Slice: 20.0000 - 200.0000
         Image width: 5.0000
            Exp time: 300.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 54.0000
                 Phi: 90.0000
                 XTD: 127.4000
              2theta: 0.0000
scan:
    Number of images: 36
               Slice: 20.0000 - 200.0000
         Image width: 5.0000
            Exp time: 300.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 0.0000
                 Phi: 0.0000
                 XTD: 127.4000
              2theta: 0.0000
scan:
    Number of images: 36
               Slice: 20.0000 - 200.0000
         Image width: 5.0000
            Exp time: 300.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 54.0000
                 Phi: 0.0000
                 XTD: 127.4000
              2theta: 0.0000
scan:
    Number of images: 9
               Slice: 42.0000 - 87.0000
         Image width: 5.0000
            Exp time: 300.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 30.0000
                 Phi: 0.0000
                 XTD: 127.4000
              2theta: 0.0000
scan:
    Number of images: 7
               Slice: 21.0000 - 56.0000
         Image width: 5.0000
            Exp time: 300.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 0.0000
                 Phi: 180.0000
                 XTD: 127.4000
              2theta: 0.0000

;
_diffrn_measurement_device
;
Crystal Goniometer
;
_diffrn_measurement_device_type
;
Rigaku RAXIS conversion
;
_diffrn_measurement_method       'profile data from \w-scans'
_diffrn_measurement_specimen_support Fiber
_diffrn_orient_matrix_type       FS_PROCESS
_diffrn_orient_matrix_UB_11      -0.084914
_diffrn_orient_matrix_UB_12      0.039066
_diffrn_orient_matrix_UB_13      0.016408
_diffrn_orient_matrix_UB_21      0.018326
_diffrn_orient_matrix_UB_22      -0.044636
_diffrn_orient_matrix_UB_23      0.063850
_diffrn_orient_matrix_UB_31      0.030399
_diffrn_orient_matrix_UB_32      0.136034
_diffrn_orient_matrix_UB_33      0.016238
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.0436
_diffrn_reflns_av_sigmaI/netI    0.0678
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            8679
_diffrn_reflns_theta_full        68.18
_diffrn_reflns_theta_max         68.18
_diffrn_reflns_theta_min         3.00
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           30.0
_diffrn_source_power             1.2
_diffrn_source_voltage           40.0
_exptl_absorpt_coefficient_mu    0.929
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.668
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.401
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       parallelepiped
_exptl_crystal_F_000             476
_exptl_crystal_size_max          0.56
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.238
_refine_diff_density_min         -0.279
_refine_diff_density_rms         0.068
_refine_ls_abs_structure_details
'Flack H D (1983), Acta Cryst. A39, 876-881; 1509 Friedel pairs'
_refine_ls_abs_structure_Flack   0.1(4)
_refine_ls_extinction_coef       0.021(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.959
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     318
_refine_ls_number_reflns         3626
_refine_ls_number_restraints     29
_refine_ls_restrained_S_all      0.956
_refine_ls_R_factor_all          0.1080
_refine_ls_R_factor_gt           0.0651
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1194P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1637
_refine_ls_wR_factor_ref         0.2109
_reflns_number_gt                1871
_reflns_number_total             3626
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            np3003832_si_002.cif
_cod_data_source_block           clqf11
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'Multi-scan' changed to
'multi-scan' according to
/usr/data/users/saulius/automatic-downloads/retrospective/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 
;
_cod_original_sg_symbol_H-M      'P 21'
_cod_original_formula_sum        'C23.50 H21 O9.50'
_cod_database_code               1516055