#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:33:20 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178432 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/53/4025360.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_4025360
loop_
_publ_author_name
'Dana K. Winter'
'Alexandre Drouin'
'Jean Lessard'
'Claude Spino'
_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+0.001xFc²λ³/sin(2θ)]^-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/[σ²(Fo²)+(0.2000P)²+0.0000P] where P=(Fo²+2Fc²)/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
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
_atom_site_disorder_assembly
_atom_site_disorder_group
H1A H 0.670(3) 0.031(3) 0.291(2) 0.073(10) Uiso 1 1 d . . .
H2A H 0.828(4) 0.158(4) 0.209(2) 0.084(11) Uiso 1 1 d . . .
C1 C 0.5700(2) 0.0271(3) 0.17336(19) 0.0534(7) Uani 1 1 d . . .
C2 C 0.4498(2) -0.0311(3) 0.10877(19) 0.0558(7) Uani 1 1 d . . .
H2 H 0.4379 0.0182 0.0512 0.067 Uiso 1 1 calc R . .
C3 C 0.4670(3) -0.1841(3) 0.0876(2) 0.0645(8) Uani 1 1 d . . .
H3A H 0.4748 -0.2388 0.1412 0.097 Uiso 1 1 calc R . .
H3B H 0.5405 -0.1941 0.0687 0.097 Uiso 1 1 calc R . .
H3C H 0.3964 -0.215 0.0399 0.097 Uiso 1 1 calc R . .
C4 C 0.3328(2) -0.0049(3) 0.13638(19) 0.0587(8) Uani 1 1 d . . .
H4A H 0.262 -0.0236 0.0841 0.07 Uiso 1 1 calc R . .
H4B H 0.3303 0.0927 0.1505 0.07 Uiso 1 1 calc R . .
C5 C 0.3163(3) -0.0875(3) 0.2168(2) 0.0636(8) Uani 1 1 d . . .
H5A H 0.2343 -0.0681 0.2224 0.076 Uiso 1 1 calc R . .
H5B H 0.3191 -0.1852 0.2032 0.076 Uiso 1 1 calc R . .
C6 C 0.4112(2) -0.0594(3) 0.3082(2) 0.0594(8) Uani 1 1 d . . .
H6A H 0.3881 -0.1116 0.3547 0.071 Uiso 1 1 calc R . .
H6B H 0.4082 0.038 0.3225 0.071 Uiso 1 1 calc R . .
C7 C 0.5446(2) -0.0970(3) 0.3119(2) 0.0564(7) Uani 1 1 d . . .
H7 H 0.5443 -0.1896 0.2859 0.068 Uiso 1 1 calc R . .
C8 C 0.6256(3) -0.1006(3) 0.4109(2) 0.0698(9) Uani 1 1 d . . .
H8A H 0.7097 -0.121 0.4129 0.105 Uiso 1 1 calc R . .
H8B H 0.5954 -0.1707 0.4432 0.105 Uiso 1 1 calc R . .
H8C H 0.6224 -0.0122 0.4386 0.105 Uiso 1 1 calc R . .
C9 C 0.9304(2) 0.1489(3) 0.32495(19) 0.0546(7) Uani 1 1 d . . .
C10 C 1.0528(2) 0.2010(3) 0.3894(2) 0.0587(7) Uani 1 1 d . . .
H10 H 1.0663 0.1473 0.4455 0.07 Uiso 1 1 calc R . .
C11 C 1.0429(3) 0.3528(3) 0.4161(2) 0.0709(9) Uani 1 1 d . . .
H11A H 1.1188 0.3803 0.46 0.106 Uiso 1 1 calc R . .
H11B H 0.9754 0.3627 0.4419 0.106 Uiso 1 1 calc R . .
H11C H 1.0284 0.4102 0.3631 0.106 Uiso 1 1 calc R . .
C12 C 1.1665(2) 0.1745(3) 0.3560(2) 0.0618(8) Uani 1 1 d . . .
H12A H 1.24 0.1885 0.4071 0.074 Uiso 1 1 calc R . .
H12B H 1.1654 0.0777 0.339 0.074 Uiso 1 1 calc R . .
C13 C 1.1813(3) 0.2607(3) 0.2764(2) 0.0617(8) Uani 1 1 d . . .
H13A H 1.1811 0.3577 0.2924 0.074 Uiso 1 1 calc R . .
H13B H 1.2617 0.2403 0.2684 0.074 Uiso 1 1 calc R . .
C14 C 1.0830(2) 0.2383(3) 0.1862(2) 0.0569(7) Uani 1 1 d . . .
H14A H 1.0839 0.1417 0.1693 0.068 Uiso 1 1 calc R . .
H14B H 1.1045 0.2928 0.14 0.068 Uiso 1 1 calc R . .
C15 C 0.9516(2) 0.2766(3) 0.18634(19) 0.0555(7) Uani 1 1 d . . .
H15 H 0.9546 0.368 0.2144 0.067 Uiso 1 1 calc R . .
C16 C 0.8658(3) 0.2855(3) 0.0895(2) 0.0650(8) Uani 1 1 d . . .
H16A H 0.862 0.197 0.0605 0.098 Uiso 1 1 calc R . .
H16B H 0.897 0.3533 0.0562 0.098 Uiso 1 1 calc R . .
H16C H 0.7842 0.3118 0.0908 0.098 Uiso 1 1 calc R . .
N1 N 0.6026(2) -0.0016(2) 0.26273(17) 0.0560(6) Uani 1 1 d . . .
N2 N 0.8963(2) 0.1796(2) 0.23642(18) 0.0574(7) Uani 1 1 d . . .
O1 O 0.63856(17) 0.0970(2) 0.14056(13) 0.0654(6) Uani 1 1 d . . .
O2 O 0.86130(16) 0.0791(2) 0.35804(13) 0.0634(6) Uani 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 0.018 0.009 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.031 0.018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.049 0.032 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 N1 120.8(2) . . ?
O1 C1 C2 118.3(2) . . ?
N1 C1 C2 120.9(2) . . ?
C4 C2 C1 115.6(2) . . ?
C4 C2 C3 113.1(2) . . ?
C1 C2 C3 110.4(2) . . ?
C2 C4 C5 117.4(2) . . ?
C6 C5 C4 115.8(2) . . ?
C5 C6 C7 114.2(3) . . ?
N1 C7 C8 107.6(2) . . ?
N1 C7 C6 114.4(2) . . ?
C8 C7 C6 109.6(3) . . ?
O2 C9 N2 120.6(2) . . ?
O2 C9 C10 117.8(2) . . ?
N2 C9 C10 121.6(3) . . ?
C9 C10 C12 114.3(2) . . ?
C9 C10 C11 111.5(2) . . ?
C12 C10 C11 112.4(2) . . ?
C13 C12 C10 118.2(2) . . ?
C14 C13 C12 115.7(2) . . ?
C13 C14 C15 114.4(2) . . ?
N2 C15 C16 107.7(2) . . ?
N2 C15 C14 114.1(2) . . ?
C16 C15 C14 110.6(2) . . ?
C1 N1 C7 129.0(2) . . ?
C9 N2 C15 129.7(2) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.239(3) . ?
C1 N1 1.344(4) . ?
C1 C2 1.534(4) . ?
C2 C4 1.520(4) . ?
C2 C3 1.539(4) . ?
C4 C5 1.528(4) . ?
C5 C6 1.523(4) . ?
C6 C7 1.532(4) . ?
C7 N1 1.461(4) . ?
C7 C8 1.530(4) . ?
C9 O2 1.246(3) . ?
C9 N2 1.336(4) . ?
C9 C10 1.530(3) . ?
C10 C12 1.536(4) . ?
C10 C11 1.536(4) . ?
C12 C13 1.530(4) . ?
C13 C14 1.518(4) . ?
C14 C15 1.526(3) . ?
C15 N2 1.463(4) . ?
C15 C16 1.524(4) . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C4 -130.3(3) . . . . ?
N1 C1 C2 C4 52.4(3) . . . . ?
O1 C1 C2 C3 99.9(3) . . . . ?
N1 C1 C2 C3 -77.4(3) . . . . ?
C1 C2 C4 C5 -72.7(3) . . . . ?
C3 C2 C4 C5 55.9(3) . . . . ?
C2 C4 C5 C6 64.4(3) . . . . ?
C4 C5 C6 C7 -62.8(3) . . . . ?
C5 C6 C7 N1 73.6(3) . . . . ?
C5 C6 C7 C8 -165.5(2) . . . . ?
O2 C9 C10 C12 131.7(3) . . . . ?
N2 C9 C10 C12 -50.0(3) . . . . ?
O2 C9 C10 C11 -99.5(3) . . . . ?
N2 C9 C10 C11 78.8(3) . . . . ?
C9 C10 C12 C13 72.2(3) . . . . ?
C11 C10 C12 C13 -56.1(3) . . . . ?
C10 C12 C13 C14 -65.2(3) . . . . ?
C12 C13 C14 C15 62.4(3) . . . . ?
C13 C14 C15 N2 -72.6(3) . . . . ?
C13 C14 C15 C16 165.9(2) . . . . ?
O1 C1 N1 C7 -170.3(3) . . . . ?
C2 C1 N1 C7 6.9(4) . . . . ?
C8 C7 N1 C1 174.8(3) . . . . ?
C6 C7 N1 C1 -63.2(4) . . . . ?
O2 C9 N2 C15 169.0(3) . . . . ?
C10 C9 N2 C15 -9.2(4) . . . . ?
C16 C15 N2 C9 -172.4(3) . . . . ?
C14 C15 N2 C9 64.4(4) . . . . ?
