Effect of Ring Size on the Exo/Endo Selectivity of a Thermal Double Cycloaddition of Fused Pyran-2-ones
Krištof Kranjc; Franc Perdih; Marijan Kočevar; Journal of Organic Chemistry 74 (2009) 6303–6306; doi:10.1021/jo9011199

data_4024775
_publ_contact_author_address
;
Faculty of Chemistry and Chemical Technology
University of Ljubljana
A\<sker\<ceva 5, P. O. Box 537
SI-1000 Ljubljana
Slovenia
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_publ_contact_author_email       kristof.kranjc@fkkt.uni-lj.si
_publ_contact_author_name        'Kri\<stof Kranjc'
_publ_section_title
;
Effect of Ring Size on the Exo/Endo Selectivity of a Thermal Double
Cycloaddition of Fused Pyran-2-ones
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              6303
_journal_page_last               6306
_journal_paper_doi               10.1021/jo9011199
_journal_volume                  74
_journal_year                    2009
_chemical_formula_sum            'C27 H29 N3 O5'
_chemical_formula_weight         475.53
_chemical_melting_point          288.5(5)
_chemical_name_systematic
;
N-[rel-(3aR,9bS,10R,14S)-2,3,3a,6,7,8,9,9b,11,12,13,14-Dodecahydro-2,12-diethyl-1,3,11,13-tetraoxo-10H-4,9a[3',4']-endo-pyrrolo-9aH-benz[e]isoindol-4(1H)-yl]benzamide
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 96.3940(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.50100(10)
_cell_length_b                   14.6602(3)
_cell_length_c                   21.9638(5)
_cell_measurement_reflns_used    5117
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.55
_cell_volume                     2400.25(8)
_computing_cell_refinement       'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_data_collection       'KappaCCD Reference Manual (Nonius, 1998)'
_computing_data_reduction        'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_molecular_graphics
'ORTEP-3 for Windows version 2.02 (Farrugia, 2008)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 0.055
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type
;
Nonius KappaCCD area-detector diffractometer
;
_diffrn_measurement_method       '\f scans + \w 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  0.0289
_diffrn_reflns_av_sigmaI/netI    0.0454
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            9925
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.93
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  0.9775
_exptl_absorpt_correction_T_min  0.9361
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.316
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1008
_exptl_crystal_size_max          0.72
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.257
_refine_diff_density_min         -0.214
_refine_diff_density_rms         0.059
_refine_ls_extinction_coef       0.043(4)
_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   1.049
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     322
_refine_ls_number_reflns         5462
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0886
_refine_ls_R_factor_gt           0.0545
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0840P)^2^+0.2099P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1370
_refine_ls_wR_factor_ref         0.1563
_reflns_number_gt                3632
_reflns_number_total             5462
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo9011199_si_001.cif
_cod_data_source_block           5Ac
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '288-289' was changed to '288.5(5)' -
the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               4024775