#------------------------------------------------------------------------------
#$Date: 2016-03-21 17:21:06 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178779 $
#$URL: svn://www.crystallography.net/cod/cif/4/10/33/4103344.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_4103344
loop_
_publ_author_name
'Masahiro Hosoya'
'Yuko Otani'
'Masatoshi Kawahata'
'Kentaro Yamaguchi'
'Tomohiko Ohwada'
_publ_section_title
;
 Water-Stable Helical Structure of Tertiary Amides of Bicyclic β-Amino
 Acid Bearing 7-Azabicyclo[2.2.1]heptane. Full Control of Amide Cis-Trans
 Equilibrium by Bridgehead Substitution
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              14780
_journal_page_last               14789
_journal_paper_doi               10.1021/ja1017877
_journal_volume                  132
_journal_year                    2010
_chemical_formula_sum            'C10 H14 Br N O3'
_chemical_formula_weight         276.13
_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                 92.979(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.7129(14)
_cell_length_b                   10.4699(16)
_cell_length_c                   12.4154(19)
_cell_measurement_reflns_used    2050
_cell_measurement_temperature    150
_cell_measurement_theta_max      25.19
_cell_measurement_theta_min      2.55
_cell_volume                     1131.0(3)
_computing_cell_refinement       'Bruker APEX2'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker APEX2'
_computing_molecular_graphics    'ORTEP-3 for Windows'
_computing_publication_material  SHELXL-97
_computing_structure_refinement  SHELXL-97
_computing_structure_solution    SHELXS-97
_diffrn_ambient_temperature      150
_diffrn_detector_area_resol_mean 8.333
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.908
_diffrn_measurement_device_type  'Bruker APEX II CCD area detector'
_diffrn_measurement_method       'φ and ω 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  0.0148
_diffrn_reflns_av_sigmaI/netI    0.0206
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5486
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         27.25
_diffrn_reflns_theta_min         2.34
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.622
_exptl_absorpt_correction_T_max  0.7364
_exptl_absorpt_correction_T_min  0.3998
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SADABS Sheldrick 1996'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.622
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.09
_refine_diff_density_max         2.646
_refine_diff_density_min         -1.754
_refine_diff_density_rms         0.126
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.138
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     138
_refine_ls_number_reflns         2298
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.138
_refine_ls_R_factor_all          0.1127
_refine_ls_R_factor_gt           0.0955
_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)+(0.0285P)²+12.4519P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1921
_refine_ls_wR_factor_ref         0.2007
_reflns_number_gt                1828
_reflns_number_total             2298
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            ja1017877_si_002_6.cif
_cod_data_source_block           45-a1001121kwh
_cod_database_code               4103344
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
C1 C 0.7119(9) -0.0621(7) 0.8813(7) 0.047(2) Uani 1 1 d .
C2 C 0.7446(13) -0.1015(9) 0.9952(8) 0.068(3) Uani 1 1 d .
H2A H 0.6487 -0.1128 1.0336 0.082 Uiso 1 1 calc R
H2B H 0.8114 -0.0388 1.0347 0.082 Uiso 1 1 calc R
C3 C 0.8287(12) -0.2309(9) 0.9805(9) 0.065(3) Uani 1 1 d .
H3 H 0.9347 -0.2262 1.0152 0.078 Uiso 1 1 calc R
C4 C 0.8376(11) -0.2414(7) 0.8604(8) 0.060(3) Uani 1 1 d .
H4 H 0.9217 -0.2979 0.8363 0.072 Uiso 1 1 calc R
C5 C 0.6759(12) -0.2738(10) 0.8108(9) 0.070(3) Uani 1 1 d .
H5A H 0.6791 -0.2942 0.7331 0.084 Uiso 1 1 calc R
H5B H 0.6296 -0.3463 0.8487 0.084 Uiso 1 1 calc R
C6 C 0.5876(12) -0.1486(10) 0.8288(9) 0.066(3) Uani 1 1 d .
H6A H 0.5458 -0.1125 0.7597 0.079 Uiso 1 1 calc R
H6B H 0.5023 -0.1621 0.8773 0.079 Uiso 1 1 calc R
C7 C 0.7429(12) -0.3490(10) 1.0245(8) 0.064(3) Uani 1 1 d .
C8 C 0.7593(12) -0.5723(9) 1.0415(8) 0.065(3) Uani 1 1 d .
H8A H 0.7317 -0.5654 1.1168 0.097 Uiso 1 1 calc R
H8B H 0.8332 -0.6421 1.0347 0.097 Uiso 1 1 calc R
H8C H 0.6668 -0.5899 0.9957 0.097 Uiso 1 1 calc R
C9 C 0.9722(8) -0.0445(7) 0.7992(6) 0.0347(15) Uani 1 1 d .
C10 C 1.1056(9) -0.1233(8) 0.7643(7) 0.049(2) Uani 1 1 d .
H10A H 1.0673 -0.1929 0.7175 0.073 Uiso 1 1 calc R
H10B H 1.1613 -0.1590 0.8280 0.073 Uiso 1 1 calc R
H10C H 1.1751 -0.0691 0.7247 0.073 Uiso 1 1 calc R
N1 N 0.8465(9) -0.1069(6) 0.8236(7) 0.064(2) Uani 1 1 d .
O1 O 0.6144(8) -0.3520(6) 1.0563(6) 0.0681(19) Uani 1 1 d .
O2 O 0.8273(8) -0.4541(7) 1.0084(7) 0.080(2) Uani 1 1 d .
O3 O 0.9792(8) 0.0696(6) 0.8029(7) 0.079(2) Uani 1 1 d .
Br1 Br 0.65229(13) 0.11428(9) 0.86455(11) 0.0795(5) Uani 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
C1 0.044(4) 0.031(4) 0.067(6) 0.005(4) 0.025(4) 0.009(3)
C2 0.086(7) 0.054(6) 0.065(7) -0.007(5) 0.008(5) 0.032(5)
C3 0.061(6) 0.052(5) 0.081(7) 0.004(5) 0.003(5) 0.023(5)
C4 0.068(6) 0.027(4) 0.089(7) 0.012(4) 0.050(5) 0.010(4)
C5 0.083(7) 0.055(6) 0.075(7) -0.003(5) 0.024(6) 0.002(5)
C6 0.069(6) 0.062(6) 0.066(7) -0.008(5) 0.009(5) 0.012(5)
C7 0.074(7) 0.057(6) 0.060(6) 0.007(5) 0.006(5) 0.018(5)
C8 0.077(7) 0.049(5) 0.069(7) 0.019(5) 0.012(5) 0.011(5)
C9 0.032(4) 0.034(4) 0.038(4) 0.007(3) -0.002(3) 0.002(3)
C10 0.037(4) 0.045(4) 0.065(6) 0.000(4) 0.014(4) -0.001(3)
N1 0.059(5) 0.030(3) 0.106(7) 0.010(4) 0.044(5) 0.009(3)
O1 0.069(4) 0.061(4) 0.078(5) 0.010(4) 0.034(4) 0.016(3)
O2 0.076(5) 0.053(4) 0.113(6) 0.020(4) 0.032(4) 0.021(4)
O3 0.062(4) 0.034(3) 0.144(7) 0.013(4) 0.041(4) 0.006(3)
Br1 0.0731(7) 0.0417(5) 0.1282(11) 0.0175(6) 0.0494(7) 0.0236(5)
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
N1 C1 C2 104.7(7)
N1 C1 C6 99.7(7)
C2 C1 C6 109.7(8)
N1 C1 Br1 117.8(5)
C2 C1 Br1 113.9(6)
C6 C1 Br1 109.9(6)
C1 C2 C3 101.4(7)
C1 C2 H2A 111.5
C3 C2 H2A 111.5
C1 C2 H2B 111.5
C3 C2 H2B 111.5
H2A C2 H2B 109.3
C4 C3 C2 103.3(8)
C4 C3 C7 109.9(8)
C2 C3 C7 114.4(8)
C4 C3 H3 109.7
C2 C3 H3 109.7
C7 C3 H3 109.7
N1 C4 C3 104.0(8)
N1 C4 C5 98.4(8)
C3 C4 C5 108.6(7)
N1 C4 H4 114.7
C3 C4 H4 114.7
C5 C4 H4 114.7
C6 C5 C4 102.0(8)
C6 C5 H5A 111.4
C4 C5 H5A 111.4
C6 C5 H5B 111.4
C4 C5 H5B 111.4
H5A C5 H5B 109.2
C1 C6 C5 102.5(8)
C1 C6 H6A 111.3
C5 C6 H6A 111.3
C1 C6 H6B 111.3
C5 C6 H6B 111.3
H6A C6 H6B 109.2
O1 C7 O2 123.5(10)
O1 C7 C3 127.2(9)
O2 C7 C3 108.7(8)
O2 C8 H8A 109.5
O2 C8 H8B 109.5
H8A C8 H8B 109.5
O2 C8 H8C 109.5
H8A C8 H8C 109.5
H8B C8 H8C 109.5
O3 C9 N1 121.7(7)
O3 C9 C10 121.2(7)
N1 C9 C10 117.1(7)
C9 C10 H10A 109.5
C9 C10 H10B 109.5
H10A C10 H10B 109.5
C9 C10 H10C 109.5
H10A C10 H10C 109.5
H10B C10 H10C 109.5
C9 N1 C1 129.8(7)
C9 N1 C4 126.6(7)
C1 N1 C4 95.5(6)
C7 O2 C8 115.1(8)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 N1 1.482(9)
C1 C2 1.486(13)
C1 C6 1.531(13)
C1 Br1 1.927(7)
C2 C3 1.556(12)
C2 H2A 0.9900
C2 H2B 0.9900
C3 C4 1.501(14)
C3 C7 1.559(14)
C3 H3 1.0000
C4 N1 1.484(10)
C4 C5 1.546(14)
C4 H4 1.0000
C5 C6 1.542(13)
C5 H5A 0.9900
C5 H5B 0.9900
C6 H6A 0.9900
C6 H6B 0.9900
C7 O1 1.206(12)
C7 O2 1.344(11)
C8 O2 1.442(11)
C8 H8A 0.9800
C8 H8B 0.9800
C8 H8C 0.9800
C9 O3 1.197(9)
C9 N1 1.324(10)
C9 C10 1.507(10)
C10 H10A 0.9800
C10 H10B 0.9800
C10 H10C 0.9800
