#------------------------------------------------------------------------------
#$Date: 2016-03-21 18:37:39 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178818 $
#$URL: svn://www.crystallography.net/cod/cif/4/10/72/4107294.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_4107294
loop_
_publ_author_name
'Chen Zhang'
'Chandra Kanta De'
'Rudrajit Mal'
'Daniel Seidel'
_publ_section_title
;
 α-Amination of Nitrogen Heterocycles: Ring-Fused Aminals
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              416
_journal_page_last               417
_journal_paper_doi               10.1021/ja077473r
_journal_volume                  130
_journal_year                    2008
_chemical_formula_sum            'C11 H12 Br2 N2'
_chemical_formula_weight         332.05
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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                 103.459(1)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   16.7608(7)
_cell_length_b                   8.7196(4)
_cell_length_c                   15.6479(6)
_cell_measurement_reflns_used    8918
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      31.99
_cell_measurement_theta_min      2.50
_cell_volume                     2224.10(16)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_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      100(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_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  0.0257
_diffrn_reflns_av_sigmaI/netI    0.0240
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            14344
_diffrn_reflns_theta_full        32.04
_diffrn_reflns_theta_max         32.04
_diffrn_reflns_theta_min         2.50
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    7.256
_exptl_absorpt_correction_T_max  0.5306
_exptl_absorpt_correction_T_min  0.1594
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'Bruker SAINT (XPREP)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.983
_exptl_crystal_description       lathe
_exptl_crystal_F_000             1296
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.699
_refine_diff_density_min         -0.611
_refine_diff_density_rms         0.112
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     140
_refine_ls_number_reflns         3845
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.005
_refine_ls_R_factor_all          0.0277
_refine_ls_R_factor_gt           0.0228
_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)+(0.0310P)²+2.5000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0557
_refine_ls_wR_factor_ref         0.0572
_reflns_number_gt                3437
_reflns_number_total             3845
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja077473r-file002.cif
_cod_data_source_block           chen246
_cod_original_cell_volume        2224.09(16)
_cod_database_code               4107294
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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
Br1 Br 0.927450(10) 0.739548(17) -0.158070(10) 0.01445(5) Uani 1 1 d .
Br2 Br 0.848772(11) 0.118331(18) -0.106710(11) 0.01879(5) Uani 1 1 d .
N1 N 0.91778(9) 0.76438(15) 0.03686(9) 0.0142(2) Uani 1 1 d .
H1 H 0.9347(16) 0.830(3) 0.0053(17) 0.030(6) Uiso 1 1 d .
N2 N 0.87960(8) 0.69589(16) 0.17110(9) 0.0137(2) Uani 1 1 d .
C1 C 0.90312(9) 0.61853(17) 0.00337(10) 0.0119(3) Uani 1 1 d .
C2 C 0.90345(9) 0.58180(17) -0.08382(10) 0.0124(3) Uani 1 1 d .
C3 C 0.88772(9) 0.43500(17) -0.11815(10) 0.0127(3) Uani 1 1 d .
H3 H 0.8898 0.4127 -0.1770 0.015 Uiso 1 1 calc R
C4 C 0.86893(9) 0.32196(18) -0.06347(10) 0.0137(3) Uani 1 1 d .
C5 C 0.86561(10) 0.35384(18) 0.02236(10) 0.0141(3) Uani 1 1 d .
H5 H 0.8512 0.2754 0.0581 0.017 Uiso 1 1 calc R
C6 C 0.88337(9) 0.50007(18) 0.05615(10) 0.0128(3) Uani 1 1 d .
C7 C 0.88576(10) 0.53347(18) 0.15157(10) 0.0154(3) Uani 1 1 d .
H7A H 0.8400 0.4782 0.1682 0.019 Uiso 1 1 calc R
H7B H 0.9377 0.4929 0.1883 0.019 Uiso 1 1 calc R
C8 C 0.93290(9) 0.79100(18) 0.13222(10) 0.0135(3) Uani 1 1 d .
H8 H 0.9919 0.7745 0.1617 0.016 Uiso 1 1 calc R
C9 C 0.90515(10) 0.95227(19) 0.14859(11) 0.0166(3) Uani 1 1 d .
H9A H 0.9182 1.0257 0.1055 0.020 Uiso 1 1 calc R
H9B H 0.9316 0.9874 0.2087 0.020 Uiso 1 1 calc R
C10 C 0.81174(10) 0.9359(2) 0.13697(12) 0.0187(3) Uani 1 1 d .
H10A H 0.7822 0.9770 0.0793 0.022 Uiso 1 1 calc R
H10B H 0.7932 0.9914 0.1840 0.022 Uiso 1 1 calc R
C11 C 0.79657(10) 0.76207(19) 0.14260(12) 0.0173(3) Uani 1 1 d .
H11A H 0.7634 0.7399 0.1859 0.021 Uiso 1 1 calc R
H11B H 0.7679 0.7207 0.0847 0.021 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'
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
C1 N1 C8 120.34(13)
C1 N1 H1 117.2(18)
C8 N1 H1 118.8(18)
C8 N2 C7 112.74(12)
C8 N2 C11 106.19(13)
C7 N2 C11 115.10(13)
N1 C1 C2 122.74(14)
N1 C1 C6 119.98(14)
C2 C1 C6 117.22(14)
C3 C2 C1 122.89(14)
C3 C2 Br1 118.55(11)
C1 C2 Br1 118.56(11)
C4 C3 C2 117.75(14)
C4 C3 H3 121.1
C2 C3 H3 121.1
C5 C4 C3 121.40(14)
C5 C4 Br2 119.22(12)
C3 C4 Br2 119.37(12)
C4 C5 C6 120.07(14)
C4 C5 H5 120.0
C6 C5 H5 120.0
C5 C6 C1 120.63(14)
C5 C6 C7 120.52(14)
C1 C6 C7 118.79(14)
N2 C7 C6 114.02(13)
N2 C7 H7A 108.7
C6 C7 H7A 108.7
N2 C7 H7B 108.7
C6 C7 H7B 108.7
H7A C7 H7B 107.6
N2 C8 N1 110.91(13)
N2 C8 C9 102.43(12)
N1 C8 C9 109.21(13)
N2 C8 H8 111.3
N1 C8 H8 111.3
C9 C8 H8 111.3
C8 C9 C10 103.68(13)
C8 C9 H9A 111.0
C10 C9 H9A 111.0
C8 C9 H9B 111.0
C10 C9 H9B 111.0
H9A C9 H9B 109.0
C9 C10 C11 105.13(13)
C9 C10 H10A 110.7
C11 C10 H10A 110.7
C9 C10 H10B 110.7
C11 C10 H10B 110.7
H10A C10 H10B 108.8
N2 C11 C10 104.18(13)
N2 C11 H11A 110.9
C10 C11 H11A 110.9
N2 C11 H11B 110.9
C10 C11 H11B 110.9
H11A C11 H11B 108.9
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C2 1.9030(15)
Br2 C4 1.9021(15)
N1 C1 1.3756(19)
N1 C8 1.473(2)
N1 H1 0.85(3)
N2 C8 1.452(2)
N2 C7 1.458(2)
N2 C11 1.476(2)
C1 C2 1.403(2)
C1 C6 1.409(2)
C2 C3 1.389(2)
C3 C4 1.389(2)
C3 H3 0.9500
C4 C5 1.385(2)
C5 C6 1.386(2)
C5 H5 0.9500
C6 C7 1.513(2)
C7 H7A 0.9900
C7 H7B 0.9900
C8 C9 1.521(2)
C8 H8 1.0000
C9 C10 1.540(2)
C9 H9A 0.9900
C9 H9B 0.9900
C10 C11 1.542(2)
C10 H10A 0.9900
C10 H10B 0.9900
C11 H11A 0.9900
C11 H11B 0.9900
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
C3 H3 N2 0.95 2.53 3.462(2) 168.2 6_565
N1 H1 Br1 0.85(3) 2.65(3) 3.0996(14) 114(2) .
C7 H7B Br1 0.99 3.18 3.7496(16) 118.1 6_566
C7 H7B Br1 0.99 3.15 3.9156(16) 135.0 5_765
C9 H9B Br1 0.99 3.18 3.9985(16) 141.4 6_576
C11 H11A Br1 0.99 3.13 3.8184(17) 127.7 7_665
N1 H1 Br2 0.85(3) 3.21(3) 3.8342(14) 133(2) 1_565
C7 H7A Br2 0.99 3.20 4.0512(17) 145.2 7_655
C8 H8 Br2 1.00 3.13 3.8542(16) 130.2 5_765
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
C8 N1 C1 C2 -167.84(14)
C8 N1 C1 C6 15.0(2)
N1 C1 C2 C3 -179.22(15)
C6 C1 C2 C3 -1.9(2)
N1 C1 C2 Br1 1.4(2)
C6 C1 C2 Br1 178.64(11)
C1 C2 C3 C4 1.7(2)
Br1 C2 C3 C4 -178.91(11)
C2 C3 C4 C5 0.2(2)
C2 C3 C4 Br2 -178.92(11)
C3 C4 C5 C6 -1.7(2)
Br2 C4 C5 C6 177.40(12)
C4 C5 C6 C1 1.4(2)
C4 C5 C6 C7 -175.69(14)
N1 C1 C6 C5 177.71(14)
C2 C1 C6 C5 0.4(2)
N1 C1 C6 C7 -5.1(2)
C2 C1 C6 C7 177.52(13)
C8 N2 C7 C6 -46.16(18)
C11 N2 C7 C6 75.85(17)
C5 C6 C7 N2 -161.88(14)
C1 C6 C7 N2 20.9(2)
C7 N2 C8 N1 54.55(17)
C11 N2 C8 N1 -72.37(15)
C7 N2 C8 C9 170.97(13)
C11 N2 C8 C9 44.05(15)
C1 N1 C8 N2 -39.59(19)
C1 N1 C8 C9 -151.75(14)
N2 C8 C9 C10 -36.57(15)
N1 C8 C9 C10 81.06(16)
C8 C9 C10 C11 16.52(17)
C8 N2 C11 C10 -33.22(16)
C7 N2 C11 C10 -158.71(13)
C9 C10 C11 N2 9.11(17)
