Effect of Ring Size on theExo/EndoSelectivity of a Thermal Double Cycloaddition of Fused Pyran-2-ones
Kranjc, Kris̆tof; Perdih, Franc; Koc̆evar, Marijan; The Journal of Organic Chemistry 74 (2009) 6303–6306; doi:10.1021/jo9011199

data_4028955
_publ_section_title
;
 Effect of Ring Size on theExo/EndoSelectivity of a Thermal Double
 Cycloaddition of Fused Pyran-2-ones
;
_journal_issue                   16
_journal_name_full               'The 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            'C29 H33 N3 O5'
_chemical_formula_weight         503.58
_chemical_melting_point          234.5(15)
_chemical_name_systematic
;
N-[rel-(3aR,11bS,12S,16R)-2,14-Diethyl-2,3,3a,6,7,8,9,10,11,11b,13,14,15,16-tetradecahydro-1,3,13,15-tetraoxo-12H-4,11a[3',4']-endo-pyrrolocyclooct[e]isoindol-4(1H)-yl]benzamide 
;
_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                 95.4690(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.5444(2)
_cell_length_b                   9.1904(2)
_cell_length_c                   25.0286(5)
_cell_measurement_reflns_used    4543
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.71
_cell_measurement_theta_min      2.55
_cell_volume                     2643.39(9)
_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 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type
;
Nonius KappaCCD area-detector diffractometer
;
_diffrn_measurement_method       '\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  0.0324
_diffrn_reflns_av_sigmaI/netI    0.0452
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            8548
_diffrn_reflns_theta_full        24.75
_diffrn_reflns_theta_max         24.75
_diffrn_reflns_theta_min         2.84
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  0.9931
_exptl_absorpt_correction_T_min  0.9786
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.265
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1072
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.157
_refine_diff_density_min         -0.179
_refine_diff_density_rms         0.034
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     403
_refine_ls_number_reflns         4478
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0843
_refine_ls_R_factor_gt           0.0492
_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^)+(0.0573P)^2^+0.7945P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1139
_refine_ls_wR_factor_ref         0.1324
_reflns_number_gt                3030
_reflns_number_total             4478
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo9011199sup2.cif
_cod_data_source_block           6Cc
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '233-236' was changed to '234.5(15)'
- the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_sg_symbol_H-M      P21/n
_cod_database_code               4028955