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#$Date: 2016-03-21 17:02:13 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178765 $
#$URL: svn://www.crystallography.net/cod/cif/4/10/19/4101903.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_4101903
loop_
_publ_author_name
'Xinqiang Fang'
'Kun Liu'
'Chaozhong Li'
_publ_section_title
;
 Efficient Regio- and Stereoselective Formation of Azocan-2-ones via
 8-EndoCyclization of α-Carbamoyl Radicals
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              2274
_journal_page_last               2283
_journal_paper_doi               10.1021/ja9082649
_journal_volume                  132
_journal_year                    2010
_chemical_formula_sum            'C10 H14 I N O3'
_chemical_formula_weight         323.12
_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                 104.543(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.536(3)
_cell_length_b                   6.2833(14)
_cell_length_c                   16.804(4)
_cell_measurement_reflns_used    1225
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      44.327
_cell_measurement_theta_min      5.406
_cell_volume                     1179.0(5)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1281
_diffrn_reflns_av_sigmaI/netI    0.1112
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            6125
_diffrn_reflns_theta_full        25.99
_diffrn_reflns_theta_max         25.99
_diffrn_reflns_theta_min         1.82
_exptl_absorpt_coefficient_mu    2.704
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75255
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.820
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.369
_exptl_crystal_size_mid          0.211
_exptl_crystal_size_min          0.045
_refine_diff_density_max         0.985
_refine_diff_density_min         -0.573
_refine_diff_density_rms         0.161
_refine_ls_extinction_coef       0.0049(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.878
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     138
_refine_ls_number_reflns         2304
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.878
_refine_ls_R_factor_all          0.0838
_refine_ls_R_factor_gt           0.0551
_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)+(0.0579P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1276
_refine_ls_wR_factor_ref         0.1396
_reflns_number_gt                1411
_reflns_number_total             2304
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja9082649_si_002.cif
_cod_data_source_block           cd27603
_cod_database_code               4101903
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
I1 I 0.54108(5) 0.41200(10) 0.18253(3) 0.0807(3) Uani 1 1 d . . .
N1 N 0.8312(4) 0.3958(7) 0.0136(3) 0.0380(11) Uani 1 1 d . . .
O1 O 0.8488(5) 0.7007(7) -0.0620(3) 0.0762(15) Uani 1 1 d . . .
O2 O 0.8376(4) 0.3757(6) -0.1169(3) 0.0547(11) Uani 1 1 d . . .
O3 O 0.8427(5) 0.6809(7) 0.0979(3) 0.0733(15) Uani 1 1 d . . .
C1 C 0.8393(5) 0.5122(10) -0.0555(4) 0.0446(15) Uani 1 1 d . . .
C2 C 0.8476(6) 0.1613(9) -0.0861(4) 0.0455(15) Uani 1 1 d . . .
H2A H 0.9302 0.1136 -0.0731 0.055 Uiso 1 1 calc R . .
H2B H 0.7993 0.0649 -0.1261 0.055 Uiso 1 1 calc R . .
C3 C 0.8018(5) 0.1725(8) -0.0098(3) 0.0366(13) Uani 1 1 d . . .
H3 H 0.8476 0.0764 0.0324 0.044 Uiso 1 1 calc R . .
C4 C 0.6683(5) 0.1279(10) -0.0250(4) 0.0494(15) Uani 1 1 d . . .
H4A H 0.6305 0.1599 -0.0821 0.059 Uiso 1 1 calc R . .
H4B H 0.6579 -0.0232 -0.0171 0.059 Uiso 1 1 calc R . .
C5 C 0.6024(5) 0.2489(10) 0.0282(4) 0.0488(15) Uani 1 1 d . . .
H5A H 0.6229 0.3983 0.0266 0.059 Uiso 1 1 calc R . .
H5B H 0.5173 0.2362 0.0033 0.059 Uiso 1 1 calc R . .
C6 C 0.6244(6) 0.1850(10) 0.1152(4) 0.0516(16) Uani 1 1 d . . .
H6 H 0.5854 0.0471 0.1167 0.062 Uiso 1 1 calc R . .
C7 C 0.7589(5) 0.1588(9) 0.1615(4) 0.0481(15) Uani 1 1 d . . .
H7A H 0.7624 0.1183 0.2178 0.058 Uiso 1 1 calc R . .
H7B H 0.7912 0.0410 0.1365 0.058 Uiso 1 1 calc R . .
C8 C 0.8418(5) 0.3501(9) 0.1641(4) 0.0410(14) Uani 1 1 d . . .
H8 H 0.8261 0.4443 0.2067 0.049 Uiso 1 1 calc R . .
C9 C 0.8346(5) 0.4906(10) 0.0900(4) 0.0439(14) Uani 1 1 d . . .
C10 C 0.9721(5) 0.2755(11) 0.1967(4) 0.0568(17) Uani 1 1 d . . .
H10A H 0.9873 0.1582 0.1641 0.085 Uiso 1 1 calc R . .
H10B H 0.9848 0.2311 0.2529 0.085 Uiso 1 1 calc R . .
H10C H 1.0254 0.3906 0.1934 0.085 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
C1 N1 C9 123.0(5) . . ?
C1 N1 C3 109.6(5) . . ?
C9 N1 C3 126.8(5) . . ?
C1 O2 C2 109.9(5) . . ?
O1 C1 O2 123.3(6) . . ?
O1 C1 N1 128.4(6) . . ?
O2 C1 N1 108.3(5) . . ?
O2 C2 C3 104.4(4) . . ?
O2 C2 H2A 110.9 . . ?
C3 C2 H2A 110.9 . . ?
O2 C2 H2B 110.9 . . ?
C3 C2 H2B 110.9 . . ?
H2A C2 H2B 108.9 . . ?
N1 C3 C2 99.6(4) . . ?
N1 C3 C4 112.1(4) . . ?
C2 C3 C4 113.8(5) . . ?
N1 C3 H3 110.3 . . ?
C2 C3 H3 110.3 . . ?
C4 C3 H3 110.3 . . ?
C5 C4 C3 116.4(5) . . ?
C5 C4 H4A 108.2 . . ?
C3 C4 H4A 108.2 . . ?
C5 C4 H4B 108.2 . . ?
C3 C4 H4B 108.2 . . ?
H4A C4 H4B 107.3 . . ?
C6 C5 C4 117.5(5) . . ?
C6 C5 H5A 107.9 . . ?
C4 C5 H5A 107.9 . . ?
C6 C5 H5B 107.9 . . ?
C4 C5 H5B 107.9 . . ?
H5A C5 H5B 107.2 . . ?
C5 C6 C7 115.1(5) . . ?
C5 C6 I1 110.3(4) . . ?
C7 C6 I1 108.8(4) . . ?
C5 C6 H6 107.4 . . ?
C7 C6 H6 107.4 . . ?
I1 C6 H6 107.4 . . ?
C8 C7 C6 117.9(5) . . ?
C8 C7 H7A 107.8 . . ?
C6 C7 H7A 107.8 . . ?
C8 C7 H7B 107.8 . . ?
C6 C7 H7B 107.8 . . ?
H7A C7 H7B 107.2 . . ?
C9 C8 C7 122.1(5) . . ?
C9 C8 C10 108.6(5) . . ?
C7 C8 C10 108.6(5) . . ?
C9 C8 H8 105.5 . . ?
C7 C8 H8 105.5 . . ?
C10 C8 H8 105.5 . . ?
O3 C9 N1 120.3(6) . . ?
O3 C9 C8 120.2(6) . . ?
N1 C9 C8 119.2(5) . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
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 C6 2.187(6) . ?
N1 C1 1.396(7) . ?
N1 C9 1.406(8) . ?
N1 C3 1.474(7) . ?
O1 C1 1.197(7) . ?
O2 C1 1.337(7) . ?
O2 C2 1.437(7) . ?
O3 C9 1.204(7) . ?
C2 C3 1.506(8) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.522(8) . ?
C3 H3 0.9800 . ?
C4 C5 1.516(8) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C6 1.476(9) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 C7 1.560(8) . ?
C6 H6 0.9800 . ?
C7 C8 1.530(8) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.512(9) . ?
C8 C10 1.538(8) . ?
C8 H8 0.9800 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
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
C2 O2 C1 O1 169.4(6) . . . . ?
C2 O2 C1 N1 -9.2(6) . . . . ?
C9 N1 C1 O1 -0.7(10) . . . . ?
C3 N1 C1 O1 171.2(6) . . . . ?
C9 N1 C1 O2 177.8(5) . . . . ?
C3 N1 C1 O2 -10.3(6) . . . . ?
C1 O2 C2 C3 24.3(6) . . . . ?
C1 N1 C3 C2 23.7(6) . . . . ?
C9 N1 C3 C2 -164.8(5) . . . . ?
C1 N1 C3 C4 -97.0(6) . . . . ?
C9 N1 C3 C4 74.5(7) . . . . ?
O2 C2 C3 N1 -27.7(5) . . . . ?
O2 C2 C3 C4 91.7(5) . . . . ?
N1 C3 C4 C5 -34.2(7) . . . . ?
C2 C3 C4 C5 -146.2(5) . . . . ?
C3 C4 C5 C6 -72.7(7) . . . . ?
C4 C5 C6 C7 48.0(7) . . . . ?
C4 C5 C6 I1 171.5(4) . . . . ?
C5 C6 C7 C8 57.2(7) . . . . ?
I1 C6 C7 C8 -67.2(6) . . . . ?
C6 C7 C8 C9 -41.3(8) . . . . ?
C6 C7 C8 C10 -168.6(5) . . . . ?
C1 N1 C9 O3 1.4(9) . . . . ?
C3 N1 C9 O3 -169.1(5) . . . . ?
C1 N1 C9 C8 -171.9(5) . . . . ?
C3 N1 C9 C8 17.6(8) . . . . ?
C7 C8 C9 O3 138.3(6) . . . . ?
C10 C8 C9 O3 -94.3(7) . . . . ?
C7 C8 C9 N1 -48.4(8) . . . . ?
C10 C8 C9 N1 79.0(6) . . . . ?
