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###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section E. It conforms to the requirements of Notes      #
# for Authors for Section E, and has been peer reviewed under the auspices   #
# of the IUCr Commission on Journals.                                        #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic. The current version number is 2.4.    #
#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
# this CIF.  For information consult the CIF home page http://www.iucr.org/  #
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data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
1-Bromomethyl-4-aza-1-azoniabicyclo[2.2.2]octane bromide
;
_chemical_name_common     ?
_chemical_formula_moiety     'C7 H14 Br N2 +, Br -'
_chemical_formula_sum     'C7 H14 Br2 N2'
_chemical_formula_structural     ?
_chemical_formula_analytical     ?
_chemical_formula_iupac     'C7 H14 Br N2 +, Br -'
_chemical_formula_weight     286.02
_chemical_melting_point     ?
_symmetry_cell_setting     'orthorhombic'
_symmetry_space_group_name_H-M     'C m c 21'
_symmetry_space_group_name_Hall     'C 2c -2'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, -y, z+1/2'
    'x, -y, z+1/2'
    '-x, y, z'
    'x+1/2, y+1/2, z'
    '-x+1/2, -y+1/2, z+1/2'
    'x+1/2, -y+1/2, z+1/2'
    '-x+1/2, y+1/2, z'
_cell_length_a     7.1100(3)
_cell_length_b     11.8085(5)
_cell_length_c     11.7702(5)
_cell_angle_alpha     90.00
_cell_angle_beta     90.00
_cell_angle_gamma     90.00
_cell_volume     988.21(7)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     3160
_cell_measurement_theta_min     3.34
_cell_measurement_theta_max     26.25
_cell_measurement_temperature     193(2)
_exptl_crystal_description     'plate'
_exptl_crystal_colour     'colourless'
_exptl_crystal_size_max     0.36
_exptl_crystal_size_mid     0.35
_exptl_crystal_size_min     0.06
_exptl_crystal_density_diffrn     1.922
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     560
loop_
    _exptl_crystal_face_index_h
    _exptl_crystal_face_index_k
    _exptl_crystal_face_index_l
    _exptl_crystal_face_perp_dist
    0.00 0.00 -1.00 0.0700
    0.00 0.00 1.00 0.1140
    0.00 -1.00 0.00 0.0070
    0.00 1.00 0.00 0.0300
    -1.00 -1.00 1.00 0.1250
    1.00 1.00 -1.00 0.1510
_exptl_absorpt_coefficient_mu     8.147
_exptl_absorpt_correction_type     'integration'
_exptl_absorpt_process_details     '(SHELXTL and XPREP; Bruker, 2005)'
_exptl_absorpt_correction_T_min     0.1511
_exptl_absorpt_correction_T_max     0.7437
_exptl_special_details
;
One distinct cell was identified using APEX2 (Bruker, 2004). Seven frame
series were integrated and filtered for statistical outliers using
SAINT (Bruker, 2005) then corrected for absorption by integration using
SHELXTL/XPREP V2005/2 (Bruker, 2005) before using
SAINT/SADABS (Bruker, 2005) to sort, merge, and scale the
combined data. No decay correction was applied.
;
_diffrn_ambient_temperature     193(2)
_diffrn_radiation_type     'MoK\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     'graphite'
_diffrn_measurement_device_type     ?
_diffrn_measurement_device     'Bruker Kappa APEXII CCD'
_diffrn_measurement_method     'φ and ω scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     7347
_diffrn_reflns_av_R_equivalents     0.0500
_diffrn_reflns_av_sigmaI/netI     0.0321
_diffrn_reflns_theta_min     3.34
_diffrn_reflns_theta_max     25.38
_diffrn_reflns_theta_full     25.38
_diffrn_measured_fraction_theta_max     0.998
_diffrn_measured_fraction_theta_full     0.998
_diffrn_reflns_limit_h_min     -8
_diffrn_reflns_limit_h_max     8
_diffrn_reflns_limit_k_min     -14
_diffrn_reflns_limit_k_max     14
_diffrn_reflns_limit_l_min     -14
_diffrn_reflns_limit_l_max     14
_diffrn_standards_number     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     ?
_refine_special_details
;
Structure was phased by direct methods (Sheldrick, 2008). Systematic conditions
suggested the ambiguous space group. The space group choice was confirmed by
successful convergence of the full-matrix least-squares refinement on
F². The highest peaks in the final difference Fourier map were in the
vicinity of atoms Br1 and Br2; the final map had no other significant
features. A final analysis of variance between observed and calculated
structure factors showed some dependence on amplitude and resolution.
;
_reflns_number_total     991
_reflns_number_gt     954
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0238
_refine_ls_R_factor_gt     0.0221
_refine_ls_wR_factor_gt     0.0509
_refine_ls_wR_factor_ref     0.0515
_refine_ls_goodness_of_fit_ref     1.104
_refine_ls_restrained_S_all     1.104
_refine_ls_number_reflns     991
_refine_ls_number_parameters     61
_refine_ls_number_restraints     1
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
                 'calc w=1/[σ²(Fo²)+(0.0248P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.418
_refine_diff_density_min     -0.439
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
_refine_ls_abs_structure_details     'Flack (1983), 468 Friedel pairs'
_refine_ls_abs_structure_Flack     -0.004(17)
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'
_computing_data_collection     'APEX2 (Bruker, 2004)'
_computing_cell_refinement     'SAINT (Bruker, 2005)'
_computing_data_reduction
;
SAINT and XPREP (Bruker, 2005)
;
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics
;
SHELXTL (Sheldrick, 2008) and CrystalMaker (CrystalMaker, 1994)
;
_computing_publication_material     'XCIF (Bruker, 2005)'
loop_
    _atom_site_type_symbol
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_calc_flag
    _atom_site_refinement_flags
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    Br Br1 0.5000 0.14054(4) -0.05638(4) 0.03174(19) Uani d S 1 . .
    Br Br2 0.0000 0.65245(4) 0.34152(3) 0.02920(17) Uani d S 1 . .
    N N1 0.5000 0.5040(4) 0.1977(4) 0.0281(9) Uani d S 1 . .
    N N2 0.5000 0.3707(3) 0.0253(3) 0.0188(8) Uani d S 1 . .
    C C1 0.5000 0.5692(5) 0.0917(5) 0.0360(13) Uani d S 1 . .
    H H1A 0.6126 0.6185 0.0898 0.043 Uiso calc PR 0.50 A -1
    H H1B 0.3874 0.6185 0.0898 0.043 Uiso calc PR 0.50 A -1
    C C2 0.5000 0.4932(4) -0.0128(4) 0.0291(12) Uani d S 1 . .
    H H2A 0.3871 0.5086 -0.0595 0.035 Uiso calc PR 0.50 B -1
    H H2B 0.6129 0.5086 -0.0595 0.035 Uiso calc PR 0.50 B -1
    C C3 0.3326(5) 0.4320(3) 0.1979(3) 0.0369(9) Uani d . 1 . .
    H H3A 0.2189 0.4804 0.1960 0.044 Uiso calc R 1 . .
    H H3B 0.3294 0.3875 0.2691 0.044 Uiso calc R 1 . .
    C C4 0.3283(5) 0.3507(3) 0.0964(3) 0.0264(8) Uani d . 1 . .
    H H4A 0.3263 0.2714 0.1236 0.032 Uiso calc R 1 . .
    H H4B 0.2137 0.3640 0.0506 0.032 Uiso calc R 1 . .
    C C5 0.5000 0.3026(4) -0.0825(4) 0.0234(10) Uani d S 1 . .
    H H5A 0.6125 0.3229 -0.1278 0.028 Uiso calc PR 0.50 C -1
    H H5B 0.3875 0.3229 -0.1278 0.028 Uiso calc PR 0.50 C -1
loop_
    _atom_site_aniso_label
    _atom_site_aniso_U_11
    _atom_site_aniso_U_22
    _atom_site_aniso_U_33
    _atom_site_aniso_U_12
    _atom_site_aniso_U_13
    _atom_site_aniso_U_23
    Br1 0.0285(4) 0.0282(3) 0.0385(4) 0.000 0.000 -0.0120(3)
    Br2 0.0230(3) 0.0325(3) 0.0321(4) 0.000 0.000 0.0042(3)
    N1 0.037(2) 0.027(2) 0.021(2) 0.000 0.000 -0.0071(18)
    N2 0.021(2) 0.023(2) 0.013(2) 0.000 0.000 -0.0006(16)
    C1 0.046(3) 0.024(3) 0.038(3) 0.000 0.000 -0.005(2)
    C2 0.042(3) 0.023(3) 0.022(3) 0.000 0.000 0.006(2)
    C3 0.039(2) 0.037(2) 0.034(2) -0.0058(18) 0.0135(16) -0.0103(18)
    C4 0.0189(18) 0.035(2) 0.0254(17) -0.0029(15) 0.0062(12) -0.0040(13)
    C5 0.032(3) 0.025(2) 0.013(2) 0.000 0.000 -0.0048(18)
_geom_special_details
;
All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes.
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    Br1 C5 . 1.938(5) ?
    N1 C3 4_655 1.463(4) ?
    N1 C3 . 1.464(4) ?
    N1 C1 . 1.466(6) ?
    N2 C4 . 1.499(4) ?
    N2 C4 4_655 1.499(4) ?
    N2 C5 . 1.502(6) ?
    N2 C2 . 1.514(6) ?
    C1 C2 . 1.522(7) ?
    C1 H1A . 0.9900 ?
    C1 H1B . 0.9900 ?
    C2 H2A . 0.9900 ?
    C2 H2B . 0.9900 ?
    C3 C4 . 1.532(4) ?
    C3 H3A . 0.9900 ?
    C3 H3B . 0.9900 ?
    C4 H4A . 0.9900 ?
    C4 H4B . 0.9900 ?
    C5 H5A . 0.9900 ?
    C5 H5B . 0.9900 ?
    Br1 Br2 6_554 3.6625(6) ?
    Br2 H5A 2_665 2.79 ?
    Br2 H5B 2_565 2.79 ?
    Br2 H4B 3_565 2.90 ?
    Br2 H4B 2_565 2.90 ?
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    C3 N1 C3 4_655 . 108.9(4) ?
    C3 N1 C1 4_655 . 107.8(3) ?
    C3 N1 C1 . . 107.8(3) ?
    C4 N2 C4 . 4_655 109.1(4) ?
    C4 N2 C5 . . 112.8(2) ?
    C4 N2 C5 4_655 . 112.8(2) ?
    C4 N2 C2 . . 108.4(2) ?
    C4 N2 C2 4_655 . 108.4(2) ?
    C5 N2 C2 . . 105.2(3) ?
    N1 C1 C2 . . 112.2(4) ?
    N1 C1 H1A . . 109.2 ?
    C2 C1 H1A . . 109.2 ?
    N1 C1 H1B . . 109.2 ?
    C2 C1 H1B . . 109.2 ?
    H1A C1 H1B . . 107.9 ?
    N2 C2 C1 . . 108.9(4) ?
    N2 C2 H2A . . 109.9 ?
    C1 C2 H2A . . 109.9 ?
    N2 C2 H2B . . 109.9 ?
    C1 C2 H2B . . 109.9 ?
    H2A C2 H2B . . 108.3 ?
    N1 C3 C4 . . 112.3(3) ?
    N1 C3 H3A . . 109.1 ?
    C4 C3 H3A . . 109.1 ?
    N1 C3 H3B . . 109.1 ?
    C4 C3 H3B . . 109.1 ?
    H3A C3 H3B . . 107.9 ?
    N2 C4 C3 . . 108.7(3) ?
    N2 C4 H4A . . 109.9 ?
    C3 C4 H4A . . 109.9 ?
    N2 C4 H4B . . 109.9 ?
    C3 C4 H4B . . 109.9 ?
    H4A C4 H4B . . 108.3 ?
    N2 C5 Br1 . . 113.2(3) ?
    N2 C5 H5A . . 108.9 ?
    Br1 C5 H5A . . 108.9 ?
    N2 C5 H5B . . 108.9 ?
    Br1 C5 H5B . . 108.9 ?
    H5A C5 H5B . . 107.7 ?
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_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    C3 N1 C1 C2 4_655 . . . 58.7(2) ?
    C3 N1 C1 C2 . . . . -58.7(2) ?
    C4 N2 C2 C1 . . . . 59.1(2) ?
    C4 N2 C2 C1 4_655 . . . -59.1(2) ?
    C5 N2 C2 C1 . . . . 180.0 ?
    N1 C1 C2 N2 . . . . 0.0 ?
    C3 N1 C3 C4 4_655 . . . -57.5(5) ?
    C1 N1 C3 C4 . . . . 59.2(4) ?
    C4 N2 C4 C3 4_655 . . . 59.3(4) ?
    C5 N2 C4 C3 . . . . -174.6(3) ?
    C2 N2 C4 C3 . . . . -58.6(3) ?
    N1 C3 C4 N2 . . . . -0.5(4) ?
    C4 N2 C5 Br1 . . . . -62.1(2) ?
    C4 N2 C5 Br1 4_655 . . . 62.1(2) ?
    C2 N2 C5 Br1 . . . . 180.0 ?
data_global
_journal_date_recd_electronic     2009-12-19
_journal_date_accepted     2010-01-04
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2010
_journal_volume     66
_journal_issue      2
_journal_page_first     o377
_journal_page_last     o377
_journal_paper_category     QO
_journal_coeditor_code     PK2223
_publ_contact_author
;
Jeffrey S. Moore
University of Illinois
School of Chemical Sciences, Box 55-5
600 South Mathews Avenue
Urbana, Illinois  61801
USA
;
_publ_contact_author_email     jsmoore@illinois.edu
_publ_contact_author_fax     '1  217 244-0181'
_publ_contact_author_phone     '1  217 244 5289'
_publ_section_title
;
1-Bromomethyl-4-aza-1-azoniabicyclo[2.2.2]octane bromide
;
loop_
    _publ_author_name
    _publ_author_address
    'Finke, Aaron D.'
;
University of Illinois
School of Chemical Sciences, Box 77-5
600 South Mathews Avenue
Urbana, Illinois 61801
USA
;
    'Gray, Danielle L.'
;
University of Illinois
School of Chemical Sciences, Box 59-1
505 South Mathews Avenue
Urbana, Illinois 61801
USA
;
    'Moore, Jeffrey S.'
;
University of Illinois
School of Chemical Sciences, Box 55-5
600 South Mathews Avenue
Urbana, Illinois 61801
USA
;
