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#$Date: 2016-03-21 02:56:18 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178412 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/33/4023325.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_4023325
loop_
_publ_author_name
'Grant R. Krow'
'Deepa Gandla'
'Weiwei Guo'
'Ryan A. Centafont'
'Guoliang Lin'
'Charles DeBrosse'
'Philip E. Sonnet'
'Ross, III, Charles W.'
'Harri G. Ramjit'
'Patrick J. Carroll'
'Kevin C. Cannon'
_publ_section_title
;
 Neighboring Group Participation in the Additions of Iodonium and
 Bromonium Ions to N-Alkoxycarbonyl-2-azabicyclo[2.2.n]alk-5-enes
 (n = 1,2)
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              2114
_journal_page_last               2121
_journal_paper_doi               10.1021/jo702153q
_journal_volume                  73
_journal_year                    2008
_chemical_formula_sum            'C8 H16 Br N O2'
_chemical_formula_weight         238.13
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      61
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   11.3026(7)
_cell_length_b                   8.0682(4)
_cell_length_c                   21.4599(13)
_cell_measurement_temperature    143(1)
_cell_volume                     1957.0(2)
_computing_data_collection       'CrystalClear (Rigaku, 1999)'
_computing_data_reduction        'CrystalClear (Rigaku, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR97 (Altomare, 1999)'
_diffrn_ambient_temperature      143(1)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device       'CCD Area Detector'
_diffrn_measurement_device_type  'Rigaku Mercury'
_diffrn_measurement_method       'phi and omega rotations'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0174
_diffrn_reflns_av_sigmaI/netI    0.0242
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            9540
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         2.62
_exptl_absorpt_coefficient_mu    4.164
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7030
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_density_diffrn    1.616
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             976
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.315
_refine_diff_density_min         -0.805
_refine_diff_density_rms         0.073
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.982
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     111
_refine_ls_number_reflns         2235
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.982
_refine_ls_R_factor_all          0.0307
_refine_ls_R_factor_gt           0.0245
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0376P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0606
_refine_ls_wR_factor_ref         0.0629
_reflns_number_gt                1831
_reflns_number_total             2235
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo702153q-File002.cif
_cod_data_source_block           shelxl
_cod_original_sg_symbol_H-M      'P b c a '
_cod_database_code               4023325
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, z'
'x, -y+1/2, z+1/2'
'-x+1/2, -y, z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, -z'
'-x, y-1/2, -z-1/2'
'x-1/2, y, -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
Br1 Br 0.729028(18) 0.64463(3) 0.200450(9) 0.02893(9) Uani 1 1 d . . .
C1 C 0.38433(15) 0.7961(2) 0.16231(8) 0.0211(4) Uani 1 1 d . . .
H1A H 0.3103 0.7399 0.1535 0.028 Uiso 1 1 calc R . .
H1B H 0.3681 0.8915 0.1884 0.028 Uiso 1 1 calc R . .
C2 C 0.47140(17) 0.6778(2) 0.19485(7) 0.0192(4) Uani 1 1 d . . .
H2 H 0.4638 0.6838 0.2403 0.026 Uiso 1 1 calc R . .
C3 C 0.46152(17) 0.4989(2) 0.17144(8) 0.0208(4) Uani 1 1 d . . .
H3A H 0.5289 0.4355 0.1861 0.028 Uiso 1 1 calc R . .
H3B H 0.3904 0.4486 0.1882 0.028 Uiso 1 1 calc R . .
C4 C 0.45738(15) 0.4933(2) 0.10025(8) 0.0186(4) Uani 1 1 d . . .
H4A H 0.3794 0.5278 0.0865 0.025 Uiso 1 1 calc R . .
H4B H 0.4692 0.3798 0.0867 0.025 Uiso 1 1 calc R . .
C5 C 0.55033(15) 0.6037(2) 0.06903(8) 0.0154(3) Uani 1 1 d . . .
H5 H 0.5239 0.6263 0.0264 0.021 Uiso 1 1 calc R . .
C6 C 0.56289(13) 0.7703(2) 0.10295(7) 0.0140(3) Uani 1 1 d . . .
H6 H 0.6216 0.8415 0.0826 0.019 Uiso 1 1 calc R . .
C7 C 0.58587(14) 0.7564(2) 0.17269(8) 0.0168(4) Uani 1 1 d . . .
H7 H 0.5882 0.8693 0.1894 0.022 Uiso 1 1 calc R . .
C8 C 0.44797(17) 1.0300(2) 0.09680(9) 0.0262(4) Uani 1 1 d . . .
H8A H 0.4899 1.0761 0.1316 0.039 Uiso 1 1 calc R . .
H8B H 0.3689 1.0734 0.0959 0.039 Uiso 1 1 calc R . .
H8C H 0.4880 1.0588 0.0589 0.039 Uiso 1 1 calc R . .
N1 N 0.44355(12) 0.84861(17) 0.10293(7) 0.0157(3) Uani 1 1 d . . .
O1 O 0.65909(10) 0.51497(14) 0.06560(5) 0.0204(3) Uani 1 1 d . . .
H1 H 0.7091 0.5725 0.0483 0.031 Uiso 1 1 calc R . .
O2 O 0.80059(13) 0.71933(18) 0.00283(7) 0.0414(4) Uani 1 1 d . . .
H2A H 0.8467 0.7034 -0.0299 0.040 Uiso 1 1 d . . .
H2B H 0.8258 0.8127 0.0188 0.040 Uiso 1 1 d . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Br1 0.02285(13) 0.03096(14) 0.03298(14) -0.00092(8) -0.01251(7) 0.00409(8)
C1 0.0168(8) 0.0256(10) 0.0208(9) -0.0045(8) 0.0038(7) 0.0004(8)
C2 0.0205(9) 0.0259(10) 0.0111(8) -0.0014(7) 0.0025(7) -0.0015(8)
C3 0.0234(9) 0.0209(9) 0.0180(9) 0.0037(7) 0.0025(7) -0.0057(8)
C4 0.0217(9) 0.0151(9) 0.0190(9) -0.0020(7) 0.0004(7) -0.0037(7)
C5 0.0186(8) 0.0158(8) 0.0119(8) -0.0002(6) 0.0012(7) 0.0010(7)
C6 0.0128(7) 0.0135(8) 0.0157(8) 0.0000(6) 0.0015(6) -0.0008(7)
C7 0.0160(8) 0.0173(8) 0.0172(8) -0.0038(7) -0.0035(7) 0.0033(7)
C8 0.0298(10) 0.0161(9) 0.0327(11) -0.0013(8) -0.0024(9) 0.0048(8)
N1 0.0152(7) 0.0146(7) 0.0172(7) -0.0015(6) -0.0007(6) 0.0026(6)
O1 0.0213(6) 0.0159(6) 0.0239(7) -0.0011(5) 0.0059(5) 0.0032(5)
O2 0.0468(9) 0.0310(8) 0.0463(9) -0.0198(7) 0.0320(7) -0.0218(7)
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'
Br Br -0.2901 2.4595 '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
N1 C1 C2 105.98(13) . . ?
C7 C2 C3 110.65(14) . . ?
C7 C2 C1 98.30(14) . . ?
C3 C2 C1 112.87(14) . . ?
C4 C3 C2 110.95(14) . . ?
C3 C4 C5 113.50(14) . . ?
O1 C5 C4 108.82(13) . . ?
O1 C5 C6 112.62(13) . . ?
C4 C5 C6 111.43(13) . . ?
N1 C6 C7 100.72(13) . . ?
N1 C6 C5 106.70(12) . . ?
C7 C6 C5 114.62(14) . . ?
C2 C7 C6 101.16(13) . . ?
C2 C7 Br1 114.83(12) . . ?
C6 C7 Br1 118.48(11) . . ?
C8 N1 C6 113.03(13) . . ?
C8 N1 C1 111.87(14) . . ?
C6 N1 C1 106.50(13) . . ?
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
Br1 C7 1.9457(16) . ?
C1 N1 1.501(2) . ?
C1 C2 1.538(3) . ?
C2 C7 1.517(2) . ?
C2 C3 1.533(2) . ?
C3 C4 1.529(2) . ?
C4 C5 1.531(2) . ?
C5 O1 1.424(2) . ?
C5 C6 1.536(2) . ?
C6 N1 1.489(2) . ?
C6 C7 1.523(2) . ?
C8 N1 1.470(2) . ?
