Substituent Effect on exo Stereoselectivity in the 1,3-Dipolar Cycloaddition Reaction of Tulipalin A with Nitrile Ylides
Petr Melša; Michal Čajan; Zdeněk Havlas; Ctibor Mazal; Journal of Organic Chemistry 73 (2008) 3032–3039; doi:10.1021/jo702563n

data_4023362
_publ_section_title
;
 Substituent Effect on exo Stereoselectivity in the 1,3-Dipolar
 Cycloaddition Reaction of Tulipalin A with Nitrile Ylides
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              3032
_journal_page_last               3039
_journal_paper_doi               10.1021/jo702563n
_journal_volume                  73
_journal_year                    2008
_chemical_formula_sum            'C19 H17 N O2'
_chemical_formula_weight         291.34
_chemical_name_systematic
; 
 (5S*,6S*)-6,8-Diphenyl-2-oxa-7-azaspiro[4.4]non-7-en-1-one  
;
_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                 100.66(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.8997(12)
_cell_length_b                   26.612(5)
_cell_length_c                   9.3887(19)
_cell_measurement_reflns_used    710
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      21.499
_cell_measurement_theta_min      2.708
_cell_volume                     1448.6(5)
_computing_cell_refinement       'KUMA KM-4 software'
_computing_data_collection       'KUMA KM-4 Crysalis V170'
_computing_data_reduction        'KUMA KM-4 software'
_computing_molecular_graphics    'SHELXTL (Bruker, 1998)'
_computing_publication_material  'SHELXTL (Bruker, 1998)'
_computing_structure_refinement  'SHELXTL (Bruker, 1998)'
_computing_structure_solution    'SHELXTL (Bruker, 1998)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean '0.06 mm'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.923
_diffrn_measurement_device_type  'Kuma KM-4 CCD diffractometer'
_diffrn_measurement_method       '\w scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0462
_diffrn_reflns_av_sigmaI/netI    0.0459
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       35
_diffrn_reflns_limit_k_min       -34
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            10568
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         28.68
_diffrn_reflns_theta_min         3.06
_diffrn_standards_decay_%        'not applicable'
_diffrn_standards_interval_count 'not applicable'
_diffrn_standards_interval_time  'not applicable'
_diffrn_standards_number         'not applicable'
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.991
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   SHELXTL
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.336
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       planar
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.222
_refine_diff_density_min         -0.218
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         3438
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.087
_refine_ls_R_factor_all          0.0755
_refine_ls_R_factor_gt           0.0484
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0594P)^2^+0.1325P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1125
_refine_ls_wR_factor_ref         0.1250
_reflns_number_gt                2477
_reflns_number_total             3438
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo702563n-File003.cif
_cod_data_source_block           melsa4
_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 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4023362