#------------------------------------------------------------------------------
#$Date: 2016-03-21 04:19:01 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178465 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/86/4028654.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_4028654
loop_
_publ_author_name
'Zachary D. Aron'
'Tatsuya Ito'
'Tricia L. May'
'Larry E. Overman'
'Jocelyn Wang'
_publ_section_title
;
 Enantioselective Synthesis of Angularly Substituted 1-Azabicylic Rings:
 Coupled Dynamic Kinetic Epimerization and Chirality Transfer
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              9929
_journal_page_last               9948
_journal_paper_doi               10.1021/jo4018099
_journal_volume                  78
_journal_year                    2013
_chemical_formula_sum            'C11 H20 Br N'
_chemical_formula_weight         246.19
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.5683(16)
_cell_length_b                   13.156(3)
_cell_length_c                   13.674(3)
_cell_measurement_temperature    158(2)
_cell_volume                     1181.6(5)
_computing_cell_refinement       'Bruker SMART/SAINT'
_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      158(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_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  0.0267
_diffrn_reflns_av_sigmaI/netI    0.0223
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            12541
_diffrn_reflns_theta_full        28.28
_diffrn_reflns_theta_max         28.28
_diffrn_reflns_theta_min         2.15
_diffrn_standards_decay_%        '< 1.0'
_diffrn_standards_interval_count 'initial 50 frames recollected'
_diffrn_standards_number         '50 frames'
_exptl_absorpt_coefficient_mu    3.439
_exptl_absorpt_correction_T_max  0.4460
_exptl_absorpt_correction_T_min  0.3549
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.384
_exptl_crystal_density_meas      ?
_exptl_crystal_description       irregular
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.28
_refine_diff_density_max         1.228
_refine_diff_density_min         -0.472
_refine_diff_density_rms         0.080
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.006(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     198
_refine_ls_number_reflns         2901
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.093
_refine_ls_R_factor_all          0.0349
_refine_ls_R_factor_gt           0.0295
_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)+(0.0452P)²+0.2632P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0718
_refine_ls_wR_factor_ref         0.0737
_reflns_number_gt                2611
_reflns_number_total             2901
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo4018099_si_003.cif
_cod_data_source_block           leo188
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'n/a' was changed to '?' - the
value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_database_code               4028654
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
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
Br1 Br 0.99889(5) 0.111060(17) 0.439909(14) 0.02816(9) Uani 1 1 d
N1 N 1.3301(3) 0.27628(18) 0.36531(15) 0.0231(4) Uani 1 1 d
C1 C 1.4937(6) 0.2025(2) 0.33339(19) 0.0334(5) Uani 1 1 d
C2 C 1.5289(5) 0.2244(2) 0.22484(19) 0.0293(6) Uani 1 1 d
C3 C 1.4630(4) 0.3352(2) 0.21318(18) 0.0249(6) Uani 1 1 d
C4 C 1.4216(5) 0.3715(2) 0.10870(19) 0.0304(6) Uani 1 1 d
C5 C 1.2355(5) 0.3210(3) 0.0627(2) 0.0327(6) Uani 1 1 d
C6 C 1.0467(4) 0.3347(2) 0.12705(19) 0.0270(6) Uani 1 1 d
C7 C 1.0864(4) 0.2920(2) 0.22929(18) 0.0213(5) Uani 1 1 d
C8 C 1.2704(4) 0.3422(2) 0.27817(16) 0.0205(5) Uani 1 1 d
C9 C 1.2275(4) 0.4511(2) 0.31241(19) 0.0254(5) Uani 1 1 d
C10 C 1.0476(4) 0.4607(2) 0.3805(2) 0.0305(7) Uani 1 1 d
C11 C 0.8747(5) 0.5044(3) 0.3578(3) 0.0346(6) Uani 1 1 d
H1 H 1.381(7) 0.315(3) 0.411(3) 0.059(12) Uiso 1 1 d
H2 H 1.202(5) 0.242(3) 0.392(3) 0.034(9) Uiso 1 1 d
H1A H 1.444(5) 0.133(3) 0.345(2) 0.035(9) Uiso 1 1 d
H1B H 1.599(6) 0.218(3) 0.372(3) 0.045(10) Uiso 1 1 d
H2A H 1.459(6) 0.179(3) 0.182(3) 0.050(11) Uiso 1 1 d
H2B H 1.683(5) 0.210(2) 0.207(2) 0.024(7) Uiso 1 1 d
H3A H 1.570(5) 0.374(2) 0.241(2) 0.019(7) Uiso 1 1 d
H4A H 1.533(5) 0.359(2) 0.068(2) 0.029(8) Uiso 1 1 d
H4B H 1.406(5) 0.447(3) 0.104(3) 0.030(8) Uiso 1 1 d
H5A H 1.255(4) 0.246(3) 0.054(2) 0.025(8) Uiso 1 1 d
H5B H 1.219(5) 0.344(3) 0.001(3) 0.047(10) Uiso 1 1 d
H6A H 1.016(5) 0.4087(19) 0.1329(18) 0.018(6) Uiso 1 1 d
H6B H 0.911(5) 0.311(2) 0.101(2) 0.030(9) Uiso 1 1 d
H7A H 0.970(5) 0.2982(19) 0.2659(19) 0.014(7) Uiso 1 1 d
H7B H 1.099(4) 0.218(2) 0.2229(19) 0.013(6) Uiso 1 1 d
H9A H 1.344(5) 0.477(2) 0.340(2) 0.021(7) Uiso 1 1 d
H9B H 1.210(6) 0.491(3) 0.255(3) 0.042(10) Uiso 1 1 d
H10A H 1.062(6) 0.431(3) 0.448(2) 0.043(10) Uiso 1 1 d
H11A H 0.853(6) 0.535(3) 0.310(3) 0.041(11) Uiso 1 1 d
H11B H 0.763(7) 0.512(3) 0.397(3) 0.053(11) 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 0.03439(13) 0.03068(13) 0.01940(12) -0.00091(8) 0.00544(13) -0.00276(17)
N1 0.0236(11) 0.0308(12) 0.0148(9) 0.0014(9) -0.0027(8) -0.0009(9)
C1 0.0280(12) 0.0406(14) 0.0315(12) 0.0067(10) 0.0009(16) 0.0087(18)
C2 0.0235(18) 0.0361(14) 0.0282(12) -0.0033(10) 0.0008(11) -0.0008(11)
C3 0.0219(15) 0.0331(13) 0.0196(10) -0.0009(10) -0.0004(9) -0.0036(10)
C4 0.0348(13) 0.0396(18) 0.0168(12) 0.0022(11) 0.0077(10) -0.0032(11)
C5 0.0425(16) 0.0430(17) 0.0126(11) 0.0002(11) -0.0006(11) -0.0035(13)
C6 0.0255(16) 0.0377(15) 0.0178(10) 0.0014(10) -0.0054(8) -0.0021(11)
C7 0.0208(11) 0.0265(14) 0.0166(11) -0.0003(9) -0.0020(10) -0.0010(10)
C8 0.0225(11) 0.0266(13) 0.0123(10) 0.0010(9) -0.0020(8) -0.0010(9)
C9 0.0289(14) 0.0282(14) 0.0193(12) -0.0019(10) -0.0025(10) -0.0005(11)
C10 0.0378(19) 0.0335(14) 0.0202(11) -0.0046(10) 0.0026(10) 0.0062(11)
C11 0.0367(17) 0.0347(16) 0.0325(16) -0.0027(14) 0.0004(13) 0.0041(13)
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 108.80(19)
N1 C1 C2 105.5(2)
C3 C2 C1 103.8(2)
C2 C3 C4 116.5(2)
C2 C3 C8 103.2(2)
C4 C3 C8 111.8(2)
C5 C4 C3 113.0(2)
C4 C5 C6 111.1(2)
C7 C6 C5 110.1(2)
C6 C7 C8 112.0(2)
N1 C8 C7 107.4(2)
N1 C8 C9 109.9(2)
C7 C8 C9 113.0(2)
N1 C8 C3 101.80(19)
C7 C8 C3 111.6(2)
C9 C8 C3 112.4(2)
C10 C9 C8 114.2(2)
C11 C10 C9 124.6(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C1 1.513(4)
N1 C8 1.525(3)
C1 C2 1.530(4)
C2 C3 1.529(4)
C3 C4 1.531(4)
C3 C8 1.549(3)
C4 C5 1.527(4)
C5 C6 1.531(4)
C6 C7 1.529(3)
C7 C8 1.531(3)
C8 C9 1.533(4)
C9 C10 1.510(4)
C10 C11 1.310(4)
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 -0.8(3)
N1 C1 C2 C3 25.3(3)
C1 C2 C3 C4 -163.0(2)
C1 C2 C3 C8 -40.1(3)
C2 C3 C4 C5 67.2(3)
C8 C3 C4 C5 -51.1(3)
C3 C4 C5 C6 54.7(3)
C4 C5 C6 C7 -57.0(3)
C5 C6 C7 C8 57.6(3)
C1 N1 C8 C7 93.9(3)
C1 N1 C8 C9 -142.8(2)
C1 N1 C8 C3 -23.5(3)
C6 C7 C8 N1 -165.2(2)
C6 C7 C8 C9 73.5(3)
C6 C7 C8 C3 -54.4(3)
C2 C3 C8 N1 38.8(2)
C4 C3 C8 N1 164.7(2)
C2 C3 C8 C7 -75.5(3)
C4 C3 C8 C7 50.4(3)
C2 C3 C8 C9 156.3(2)
C4 C3 C8 C9 -77.8(3)
N1 C8 C9 C10 -64.2(3)
C7 C8 C9 C10 55.7(3)
C3 C8 C9 C10 -176.8(2)
C8 C9 C10 C11 -110.6(3)
