Unexpected Diels-Alder/Carbonyl-ene Cascade toward the Biomimetic Synthesis of Chloropupukeananin.
Suzuki, Takahiro; Miyajima, Yuria; Suzuki, Kaname; Iwakiri, Kanako; Koshimizu, Masaki; Hirai, Go; Sodeoka, Mikiko; Kobayashi, Susumu; Organic letters 15 (2013) 1748–1751; doi:10.1021/ol400549q

data_1511917
_publ_section_title
;
 Unexpected Diels-Alder/Carbonyl-ene Cascade toward the Biomimetic
 Synthesis of Chloropupukeananin.
;
_journal_issue                   7
_journal_name_full               'Organic letters'
_journal_page_first              1748
_journal_page_last               1751
_journal_paper_doi               10.1021/ol400549q
_journal_volume                  15
_journal_year                    2013
_chemical_formula_moiety         '2(C27 H27 Cl O8), C4 H8 O2'
_chemical_formula_sum            'C58 H62 Cl2 O18'
_chemical_formula_weight         1117.98
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 98.997(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.2073(18)
_cell_length_b                   19.249(3)
_cell_length_c                   21.407(3)
_cell_measurement_reflns_used    2503
_cell_measurement_temperature    173(1)
_cell_measurement_theta_max      20.84
_cell_measurement_theta_min      2.20
_cell_volume                     5375.3(13)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(1)
_diffrn_detector_area_resol_mean 8.333
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0789
_diffrn_reflns_av_sigmaI/netI    0.1217
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            29447
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         1.96
_exptl_absorpt_coefficient_mu    0.197
_exptl_absorpt_correction_T_max  0.9961
_exptl_absorpt_correction_T_min  0.9617
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
;
SADABS; Sheldrick 1996
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.381
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             2352
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.490
_refine_diff_density_min         -0.400
_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.130
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     718
_refine_ls_number_reflns         12148
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.130
_refine_ls_R_factor_all          0.1440
_refine_ls_R_factor_gt           0.0629
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0692
_refine_ls_wR_factor_ref         0.0804
_reflns_number_gt                6325
_reflns_number_total             12148
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol400549q_si_001.cif
_cod_data_source_block           cpk_ene
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_cell_volume        5375.3(12)
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               1511917