Photochemical Rearrangement of N-Chlorolactams: A Route to N-Heterocycles through Concerted Ring Contraction
Dana K. Winter; Alexandre Drouin; Jean Lessard; Claude Spino; Journal of Organic Chemistry 75 (2010) 2610–2618; doi:10.1021/jo100181h

data_4025360
_publ_section_title
;
 Photochemical Rearrangement of N-Chlorolactams: A Route to N-Heterocycles
 through Concerted Ring Contraction
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              2610
_journal_page_last               2618
_journal_paper_doi               10.1021/jo100181h
_journal_volume                  75
_journal_year                    2010
_chemical_formula_sum            'C8 H15 N O'
_chemical_formula_weight         141.21
_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             2005-07-25T14:45:24-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 106.96(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   11.270(4)
_cell_length_b                   9.666(6)
_cell_length_c                   15.380(7)
_cell_measurement_reflns_used    24
_cell_measurement_temperature    191(2)
_cell_measurement_theta_max      45
_cell_measurement_theta_min      34
_cell_volume                     1602.6(14)
_computing_cell_refinement       Difrac
_computing_data_collection       Difrac
_computing_data_reduction        NRCVAX
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      191(2)
_diffrn_measured_fraction_theta_full 0.912
_diffrn_measured_fraction_theta_max 0.912
_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     0.0218
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            2787
_diffrn_reflns_theta_full        70.37
_diffrn_reflns_theta_max         70.37
_diffrn_reflns_theta_min         4.1
_diffrn_standards_decay_%        5.9
_diffrn_standards_interval_count 100
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    0.602
_exptl_absorpt_correction_T_max  0.8548
_exptl_absorpt_correction_T_min  0.2755
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'psi scan'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.17
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.355
_refine_diff_density_min         -0.271
_refine_diff_density_rms         0.067
_refine_ls_extinction_coef       0.0019(10)
_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   0.953
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     194
_refine_ls_number_reflns         2787
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.953
_refine_ls_R_factor_all          0.1226
_refine_ls_R_factor_gt           0.0865
_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          0.2354
_refine_ls_wR_factor_ref         0.2674
_reflns_number_gt                1688
_reflns_number_total             2787
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo100181h_si_001.cif
_cod_data_source_block           ad2055
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'Empirical' changed to
'empirical' 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 1646 2011-03-28 12:23:43Z adriana 
;
_cod_original_cell_volume        1602.7(13)
_cod_database_code               4025360