Acid-Mediated Ring-Expansion Reaction of N-Aryl-2-vinylazetidines: Synthesis and Unanticipated Reactivity of Tetrahydrobenzazocines.
Shimizu, Tomoaki; Koya, Shunsuke; Yamasaki, Ryu; Mutoh, Yuichiro; Azumaya, Isao; Katagiri, Kosuke; Saito, Shinichi; The Journal of organic chemistry 79 (2014) 4367–4377; doi:10.1021/jo500249c

data_4029377
_publ_section_title
;
 Acid-Mediated Ring-Expansion Reaction of N-Aryl-2-vinylazetidines:
 Synthesis and Unanticipated Reactivity of Tetrahydrobenzazocines.
;
_journal_issue                   10
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              4367
_journal_page_last               4377
_journal_paper_doi               10.1021/jo500249c
_journal_volume                  79
_journal_year                    2014
_chemical_formula_sum            'C13 H17 N O2'
_chemical_formula_weight         219.28
_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                 92.305(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.401(3)
_cell_length_b                   12.000(3)
_cell_length_c                   8.479(2)
_cell_measurement_reflns_used    5033
_cell_measurement_temperature    120
_cell_measurement_theta_max      25.81
_cell_measurement_theta_min      2.47
_cell_volume                     1159.1(5)
_computing_cell_refinement       'APEX2 (Bruker AXS, 2006)'
_computing_data_collection       'APEX2 (Bruker AXS, 2006)'
_computing_data_reduction        'SAINT (Bruker AXS, 2004)'
_computing_molecular_graphics    'XSHEL (Bruker AXS,2002)'
_computing_publication_material  'XCIF (Bruker AXS, 2001)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      120
_diffrn_detector_area_resol_mean 8.333
_diffrn_measured_fraction_theta_full 0.968
_diffrn_measured_fraction_theta_max 0.931
_diffrn_measurement_device_type  'Bruker APEXII CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0715
_diffrn_reflns_av_sigmaI/netI    0.0633
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            8621
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.95
_diffrn_reflns_theta_min         1.79
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  0.9751
_exptl_absorpt_correction_T_min  0.9710
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
;
SADABS Sheldrick 1996
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.257
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.399
_refine_diff_density_min         -0.328
_refine_diff_density_rms         0.091
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     151
_refine_ls_number_reflns         2113
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0806
_refine_ls_R_factor_gt           0.0753
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1792P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2139
_refine_ls_wR_factor_ref         0.2236
_reflns_number_gt                1826
_reflns_number_total             2113
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo500249c_si_001.cif
_cod_data_source_block           compound_3b
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 

 Adding full bibliography for 4029376--4029377.cif.
;
_cod_original_sg_symbol_H-M      'P2(1)/c  '
_cod_database_code               4029377