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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/4/02/33/4023326.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_4023326
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            'C12 H20 I N O3'
_chemical_formula_weight         353.19
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 105.701(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.8678(14)
_cell_length_b                   11.6482(13)
_cell_length_c                   12.8796(18)
_cell_measurement_temperature    143(1)
_cell_volume                     1425.2(3)
_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 0.953
_diffrn_measured_fraction_theta_max 0.953
_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  0.0150
_diffrn_reflns_av_sigmaI/netI    0.0151
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            8968
_diffrn_reflns_theta_full        27.47
_diffrn_reflns_theta_max         27.47
_diffrn_reflns_theta_min         2.77
_exptl_absorpt_coefficient_mu    2.245
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8072
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_density_diffrn    1.646
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.624
_refine_diff_density_min         -1.316
_refine_diff_density_rms         0.087
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.110
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     159
_refine_ls_number_reflns         3113
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.110
_refine_ls_R_factor_all          0.0257
_refine_ls_R_factor_gt           0.0241
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0304P)²+0.9256P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0580
_refine_ls_wR_factor_ref         0.0592
_reflns_number_gt                2924
_reflns_number_total             3113
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo702153q-File003.cif
_cod_data_source_block           shelxl
_cod_original_sg_symbol_H-M      'P 21/n     '
_cod_database_code               4023326
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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
I1 I 0.805151(16) 0.213727(12) 0.974468(11) 0.03297(7) Uani 1 1 d . . .
C1 C 0.6029(2) 0.43615(18) 0.70069(14) 0.0211(4) Uani 1 1 d . . .
H1A H 0.6320 0.4999 0.6633 0.028 Uiso 1 1 calc R . .
H1B H 0.5378 0.3882 0.6487 0.028 Uiso 1 1 calc R . .
C2 C 0.73081(19) 0.36651(17) 0.76534(14) 0.0196(4) Uani 1 1 d . . .
H2 H 0.7530 0.3034 0.7224 0.026 Uiso 1 1 calc R . .
C3 C 0.8596(2) 0.44234(19) 0.81171(16) 0.0245(4) Uani 1 1 d . . .
H3A H 0.8985 0.4668 0.7538 0.033 Uiso 1 1 calc R . .
H3B H 0.9309 0.3979 0.8624 0.033 Uiso 1 1 calc R . .
C4 C 0.8225(2) 0.54817(18) 0.86895(17) 0.0263(4) Uani 1 1 d . . .
H4A H 0.9089 0.5839 0.9106 0.035 Uiso 1 1 calc R . .
H4B H 0.7738 0.6030 0.8151 0.035 Uiso 1 1 calc R . .
C5 C 0.7303(2) 0.52138(17) 0.94404(15) 0.0219(4) Uani 1 1 d . . .
H5 H 0.6837 0.5924 0.9563 0.029 Uiso 1 1 calc R . .
C6 C 0.61618(18) 0.43300(17) 0.89249(14) 0.0183(4) Uani 1 1 d . . .
H6 H 0.5529 0.4180 0.9379 0.024 Uiso 1 1 calc R . .
C7 C 0.67025(19) 0.32202(17) 0.85490(15) 0.0201(4) Uani 1 1 d . . .
H7 H 0.5872 0.2761 0.8199 0.027 Uiso 1 1 calc R . .
C8 C 0.42376(19) 0.54274(17) 0.77004(15) 0.0206(4) Uani 1 1 d . . .
C9 C 0.2407(2) 0.63632(18) 0.62843(15) 0.0221(4) Uani 1 1 d . . .
C10 C 0.2565(3) 0.7540(2) 0.68110(19) 0.0332(5) Uani 1 1 d . . .
H10A H 0.2658 0.7457 0.7569 0.050 Uiso 1 1 calc R . .
H10B H 0.1749 0.7996 0.6489 0.050 Uiso 1 1 calc R . .
H10C H 0.3388 0.7911 0.6708 0.050 Uiso 1 1 calc R . .
C11 C 0.2257(2) 0.6464(2) 0.50810(16) 0.0316(5) Uani 1 1 d . . .
H11A H 0.3066 0.6848 0.4969 0.047 Uiso 1 1 calc R . .
H11B H 0.1425 0.6896 0.4746 0.047 Uiso 1 1 calc R . .
H11C H 0.2184 0.5711 0.4768 0.047 Uiso 1 1 calc R . .
C12 C 0.1198(2) 0.5676(2) 0.64877(19) 0.0326(5) Uani 1 1 d . . .
H12A H 0.1265 0.4893 0.6274 0.049 Uiso 1 1 calc R . .
H12B H 0.0320 0.5997 0.6076 0.049 Uiso 1 1 calc R . .
H12C H 0.1243 0.5703 0.7241 0.049 Uiso 1 1 calc R . .
N1 N 0.53953(16) 0.47688(15) 0.78553(12) 0.0204(3) Uani 1 1 d . . .
O1 O 0.37515(15) 0.57362(14) 0.84349(11) 0.0285(3) Uani 1 1 d . . .
O2 O 0.37237(14) 0.56951(13) 0.66539(10) 0.0235(3) Uani 1 1 d . . .
O3 O 0.81803(14) 0.48325(14) 1.04449(11) 0.0274(3) Uani 1 1 d . . .
H3 H 0.7691 0.4632 1.0836 0.041 Uiso 1 1 calc R . .
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'
I I -0.4742 1.8119 '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 102.60(14) . . ?
C7 C2 C3 110.78(15) . . ?
C7 C2 C1 98.98(14) . . ?
C3 C2 C1 112.28(17) . . ?
C2 C3 C4 111.80(16) . . ?
C5 C4 C3 113.65(17) . . ?
O3 C5 C4 108.64(16) . . ?
O3 C5 C6 112.27(16) . . ?
C4 C5 C6 110.80(15) . . ?
N1 C6 C7 97.61(14) . . ?
N1 C6 C5 107.60(15) . . ?
C7 C6 C5 115.23(15) . . ?
C2 C7 C6 101.19(15) . . ?
C2 C7 I1 116.57(12) . . ?
C6 C7 I1 118.12(12) . . ?
O1 C8 O2 125.95(17) . . ?
O1 C8 N1 123.18(17) . . ?
O2 C8 N1 110.87(16) . . ?
O2 C9 C12 109.29(16) . . ?
O2 C9 C10 110.84(16) . . ?
C12 C9 C10 112.96(18) . . ?
O2 C9 C11 101.72(15) . . ?
C12 C9 C11 110.64(18) . . ?
C10 C9 C11 110.81(18) . . ?
C8 N1 C6 122.51(15) . . ?
C8 N1 C1 125.88(15) . . ?
C6 N1 C1 111.58(14) . . ?
C8 O2 C9 120.39(14) . . ?
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
I1 C7 2.1506(19) . ?
C1 N1 1.476(2) . ?
C1 C2 1.541(3) . ?
C2 C7 1.526(3) . ?
C2 C3 1.530(3) . ?
C3 C4 1.531(3) . ?
C4 C5 1.529(3) . ?
C5 O3 1.420(2) . ?
C5 C6 1.537(3) . ?
C6 N1 1.472(2) . ?
C6 C7 1.526(3) . ?
C8 O1 1.225(2) . ?
C8 O2 1.342(2) . ?
C8 N1 1.345(2) . ?
C9 O2 1.479(2) . ?
C9 C12 1.517(3) . ?
C9 C10 1.519(3) . ?
C9 C11 1.521(3) . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O3 H3 O1 0.82 1.95 2.765(2) 169.8 3_667
