Photochemical Rearrangement of N-Mesyloxylactams: Stereospecific Formation of N-Heterocycles
Alexandre Drouin; Dana K. Winter; Simon Pichette; Samuel Aubert-Nicol; Jean Lessard; Claude Spino; Journal of Organic Chemistry 76 (2011) 164–169; doi:10.1021/jo101805q

data_4025953
_publ_section_title
;
 Photochemical Rearrangement of N-Mesyloxylactams: Stereospecific
 Formation of N-Heterocycles
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              164
_journal_page_last               169
_journal_paper_doi               10.1021/jo101805q
_journal_volume                  76
_journal_year                    2011
_chemical_formula_sum            'C16 H19 N O4'
_chemical_formula_weight         289.32
_chemical_name_systematic
;
 ?
;
_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_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.3
_audit_creation_date             2009-06-23T09:41:02-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 91.05(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.449(2)
_cell_length_b                   5.8194(7)
_cell_length_c                   23.624(11)
_cell_measurement_reflns_used    20
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      35
_cell_measurement_theta_min      30
_cell_volume                     1436.3(7)
_computing_cell_refinement       Difrac
_computing_data_collection       Difrac
_computing_data_reduction        NRCVAX
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.951
_diffrn_measured_fraction_theta_max 0.951
_diffrn_measurement_device_type  CAD4
_diffrn_measurement_method       Omega
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54176
_diffrn_reflns_av_R_equivalents  0
_diffrn_reflns_av_unetI/netI     0.0272
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            2591
_diffrn_reflns_theta_full        70
_diffrn_reflns_theta_max         70
_diffrn_reflns_theta_min         4.23
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 100
_diffrn_standards_number         1
_exptl_absorpt_coefficient_mu    0.791
_exptl_absorpt_correction_T_max  0.8906
_exptl_absorpt_correction_T_min  0.6483
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   empirical
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.338
_exptl_crystal_description       Needdle
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.341
_refine_diff_density_min         -0.269
_refine_diff_density_rms         0.078
_refine_ls_extinction_coef       0.014(3)
_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   1.205
_refine_ls_hydrogen_treatment    none
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         2591
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.205
_refine_ls_R_factor_all          0.151
_refine_ls_R_factor_gt           0.1037
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.2000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2997
_refine_ls_wR_factor_ref         0.3384
_reflns_number_gt                1567
_reflns_number_total             2591
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo101805q_si_001.cif
_cod_data_source_block           dw5142
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'Psi-scan' changed to
'psi-scan' according to the built-in table from CIF Core dictionary
named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               4025953