#------------------------------------------------------------------------------
#$Date: 2016-03-21 04:32:49 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178472 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/93/4029377.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4029377
loop_
_publ_author_name
'Shimizu, Tomoaki'
'Koya, Shunsuke'
'Yamasaki, Ryu'
'Mutoh, Yuichiro'
'Azumaya, Isao'
'Katagiri, Kosuke'
'Saito, Shinichi'
_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
_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_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/[σ²(Fo²)+(0.1792P)²+0.0000P] where P=(Fo²+2Fc²)/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
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
O1 O 0.36031(11) 0.19372(10) 0.16008(15) 0.0282(4) Uani 1 1 d .
O2 O 0.27188(11) 0.00565(10) 0.02497(13) 0.0278(4) Uani 1 1 d .
N1 N 0.00186(13) 0.24831(12) 0.43813(17) 0.0243(4) Uani 1 1 d .
C6 C 0.18263(15) 0.22084(14) 0.30584(19) 0.0227(5) Uani 1 1 d .
H6 H 0.2116 0.2880 0.3522 0.027 Uiso 1 1 calc R
C3 C 0.09778(15) 0.02544(14) 0.17197(19) 0.0209(5) Uani 1 1 d .
H3 H 0.0692 -0.0419 0.1258 0.025 Uiso 1 1 calc R
C4 C 0.02636(14) 0.08377(14) 0.27500(17) 0.0201(5) Uani 1 1 d .
C1 C 0.25204(15) 0.16176(14) 0.20307(19) 0.0227(5) Uani 1 1 d .
C2 C 0.20763(15) 0.06233(14) 0.13545(18) 0.0218(5) Uani 1 1 d .
C5 C 0.07095(15) 0.18265(14) 0.34167(18) 0.0208(5) Uani 1 1 d .
C7 C -0.09373(15) 0.04137(14) 0.31371(19) 0.0230(5) Uani 1 1 d .
H7A H -0.0852 -0.0186 0.3935 0.028 Uiso 1 1 calc R
H7B H -0.1322 0.0091 0.2174 0.028 Uiso 1 1 calc R
C9 C -0.10346(16) 0.20115(15) 0.5020(2) 0.0285(5) Uani 1 1 d .
H9A H -0.1537 0.2619 0.5403 0.034 Uiso 1 1 calc R
H9B H -0.0816 0.1526 0.5928 0.034 Uiso 1 1 calc R
C12 C -0.28171(16) 0.08697(16) 0.4420(2) 0.0302(5) Uani 1 1 d .
H12 H -0.2740 0.0394 0.5314 0.036 Uiso 1 1 calc R
C8 C -0.17168(15) 0.13366(14) 0.37720(19) 0.0257(5) Uani 1 1 d .
H8 H -0.1944 0.1846 0.2878 0.031 Uiso 1 1 calc R
C10 C 0.39908(19) 0.30213(16) 0.2128(3) 0.0382(6) Uani 1 1 d .
H10A H 0.3429 0.3586 0.1742 0.057 Uiso 1 1 calc R
H10B H 0.4765 0.3179 0.1717 0.057 Uiso 1 1 calc R
H10C H 0.4042 0.3037 0.3284 0.057 Uiso 1 1 calc R
C11 C 0.36307(16) -0.06232(16) 0.0945(2) 0.0340(5) Uani 1 1 d .
H11A H 0.4167 -0.0158 0.1594 0.051 Uiso 1 1 calc R
H11B H 0.4066 -0.0982 0.0110 0.051 Uiso 1 1 calc R
H11C H 0.3285 -0.1196 0.1607 0.051 Uiso 1 1 calc R
C13 C -0.38795(17) 0.10710(17) 0.3840(2) 0.0391(6) Uani 1 1 d .
H13A H -0.3990 0.1543 0.2947 0.047 Uiso 1 1 calc R
H13B H -0.4538 0.0745 0.4314 0.047 Uiso 1 1 calc R
H1 H 0.0418(19) 0.2923(19) 0.503(3) 0.039(6) Uiso 1 1 d .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C1 O1 C10 116.33(14)
C2 O2 C11 113.28(13)
C5 N1 C9 119.44(14)
C5 N1 H1 114.5(15)
C9 N1 H1 114.7(15)
C1 C6 C5 120.92(16)
C1 C6 H6 119.5
C5 C6 H6 119.5
C2 C3 C4 122.37(16)
C2 C3 H3 118.8
C4 C3 H3 118.8
C5 C4 C3 117.58(16)
C5 C4 C7 121.03(15)
C3 C4 C7 121.39(15)
O1 C1 C6 124.73(16)
O1 C1 C2 116.49(15)
C6 C1 C2 118.77(16)
C3 C2 O2 120.24(15)
C3 C2 C1 119.77(15)
O2 C2 C1 119.88(15)
C6 C5 N1 118.75(15)
C6 C5 C4 120.58(15)
N1 C5 C4 120.57(15)
C4 C7 C8 112.15(14)
C4 C7 H7A 109.2
C8 C7 H7A 109.2
C4 C7 H7B 109.2
C8 C7 H7B 109.2
H7A C7 H7B 107.9
N1 C9 C8 110.81(14)
N1 C9 H9A 109.5
C8 C9 H9A 109.5
N1 C9 H9B 109.5
C8 C9 H9B 109.5
H9A C9 H9B 108.1
C13 C12 C8 124.59(18)
C13 C12 H12 117.7
C8 C12 H12 117.7
C12 C8 C9 110.85(14)
C12 C8 C7 111.40(15)
C9 C8 C7 109.99(14)
C12 C8 H8 108.2
C9 C8 H8 108.2
C7 C8 H8 108.2
O1 C10 H10A 109.5
O1 C10 H10B 109.5
H10A C10 H10B 109.5
O1 C10 H10C 109.5
H10A C10 H10C 109.5
H10B C10 H10C 109.5
O2 C11 H11A 109.5
O2 C11 H11B 109.5
H11A C11 H11B 109.5
O2 C11 H11C 109.5
H11A C11 H11C 109.5
H11B C11 H11C 109.5
C12 C13 H13A 120.0
C12 C13 H13B 120.0
H13A C13 H13B 120.0
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.356(2)
O1 C10 1.439(2)
O2 C2 1.390(2)
O2 C11 1.430(2)
N1 C5 1.401(2)
N1 C9 1.452(2)
N1 H1 0.88(2)
C6 C1 1.394(2)
C6 C5 1.398(2)
C6 H6 0.9500
C3 C2 1.375(3)
C3 C4 1.405(2)
C3 H3 0.9500
C4 C5 1.401(2)
C4 C7 1.509(2)
C1 C2 1.409(2)
C7 C8 1.531(2)
C7 H7A 0.9900
C7 H7B 0.9900
C9 C8 1.521(3)
C9 H9A 0.9900
C9 H9B 0.9900
C12 C13 1.311(3)
C12 C8 1.498(2)
C12 H12 0.9500
C8 H8 1.0000
C10 H10A 0.9800
C10 H10B 0.9800
C10 H10C 0.9800
C11 H11A 0.9800
C11 H11B 0.9800
C11 H11C 0.9800
C13 H13A 0.9500
C13 H13B 0.9500
