##############################################################################
###                                                                        ###
###        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_global
_audit_creation_method     'by CrystalStructure 3.7.0'
_journal_date_recd_electronic     2008-03-04
_journal_date_accepted     2008-04-27
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2008
_journal_volume     64
_journal_issue      6
_journal_page_first     o1025
_journal_page_last     o1025
_journal_paper_category     QO
_journal_coeditor_code     CS2071
_publ_contact_author_name     'Dr. Shuping Luo'
_publ_contact_author_address
;
State Key Laboratory Breeding Base of Green Chemistry-Synthesis Technology
Zhejiang University of Technology
Hangzhou
310014
People's Republic of China
;
_publ_contact_author_email     yifengwang108@gmail.com
_publ_contact_author_fax     '86 571 88320066'
_publ_contact_author_phone     '86 571 88320609'
_publ_section_title
;
(S)-1-(2-Ammonio-3-methylbutyl)-1,2-dihydropyridin-2-iminium dibromide
;
loop_
    _publ_author_name
    _publ_author_address
    'Yifeng Wang'
;
State Key Laboratory Breeding Base of Green Chemistry--Synthesis Technology
Zhejiang University of Technology
Hangzhou 310014
People's Republic of China
;
    'Jixv Zhang'
;
State Key Laboratory Breeding Base of Green Chemistry--Synthesis Technology
Zhejiang University of Technology
Hangzhou 310014
People's Republic of China
;
    'Hui Chen'
;
State Key Laboratory Breeding Base of Green Chemistry--Synthesis Technology
Zhejiang University of Technology
Hangzhou 310014
People's Republic of China
;
    'Shuping Luo'
;
State Key Laboratory Breeding Base of Green Chemistry--Synthesis Technology
Zhejiang University of Technology
Hangzhou 310014
People's Republic of China
;
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
(S)-1-(2-Ammonio-3-methylbutyl)-1,2-dihydropyridin-2-iminium dibromide
;
_chemical_name_common     ?
_chemical_formula_moiety     'C10 H19 N3 2+, 2(Br -)'
_chemical_formula_sum     'C10 H19 Br2 N3'
_chemical_formula_iupac     'C10 H19 N3 2+, 2Br -'
_chemical_formula_weight     341.10
_chemical_melting_point     ?
_symmetry_cell_setting     Monoclinic
_symmetry_space_group_name_H-M     'P 21'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, y+1/2, -z'
_cell_length_a     5.9311(11)
_cell_length_b     12.456(2)
_cell_length_c     9.6807(18)
_cell_angle_alpha     90.00
_cell_angle_beta     99.733(3)
_cell_angle_gamma     90.00
_cell_volume     704.9(2)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     1818
_cell_measurement_theta_min     5.378
_cell_measurement_theta_max     53.439
_cell_measurement_temperature     293(2)
_exptl_crystal_description     prismatic
_exptl_crystal_colour     colorless
_exptl_crystal_size_max     0.446
_exptl_crystal_size_mid     0.337
_exptl_crystal_size_min     0.203
_exptl_crystal_density_diffrn     1.607
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     340
_exptl_absorpt_coefficient_mu     5.727
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Sheldrick, 1996)'
_exptl_absorpt_correction_T_min     0.38123
_exptl_absorpt_correction_T_max     1.00000
_exptl_special_details
;
;
_diffrn_ambient_temperature     293(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     'Bruker SMART APEX CCD'
_diffrn_measurement_method     'φ and ω'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     4117
_diffrn_reflns_av_R_equivalents     0.0382
_diffrn_reflns_av_sigmaI/netI     0.0510
_diffrn_reflns_theta_min     2.13
_diffrn_reflns_theta_max     26.99
_diffrn_reflns_theta_full     26.99
_diffrn_measured_fraction_theta_max     0.990
_diffrn_measured_fraction_theta_full     0.990
_diffrn_reflns_limit_h_min     -7
_diffrn_reflns_limit_h_max     7
_diffrn_reflns_limit_k_min     -12
_diffrn_reflns_limit_k_max     15
_diffrn_reflns_limit_l_min     -12
_diffrn_reflns_limit_l_max     12
_diffrn_standards_number     ?
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     ?
_refine_special_details
;
;
_reflns_number_total     2307
_reflns_number_gt     2054
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0451
_refine_ls_R_factor_gt     0.0408
_refine_ls_wR_factor_gt     0.0906
_refine_ls_wR_factor_ref     0.0919
_refine_ls_goodness_of_fit_ref     0.986
_refine_ls_restrained_S_all     0.985
_refine_ls_number_reflns     2307
_refine_ls_number_parameters     147
_refine_ls_number_restraints     3
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
                 'calc w=1/[σ²(Fo²)+(0.0533P)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     0.910
_refine_diff_density_min     -0.706
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
_refine_ls_abs_structure_details     'Flack (1983), 696 Friedel pairs'
_refine_ls_abs_structure_Flack     0.06(2)
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     'SMART (Bruker, 2001)'
_computing_cell_refinement     'SMART (Bruker, 2001)'
_computing_data_reduction     'SAINT-Plus (Bruker, 2000)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics     'SHELXTL (Sheldrick, 2008)'
_computing_publication_material     'SHELXTL (Sheldrick, 2008)'
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 1.02019(11) 0.21057(4) 0.84434(6) 0.03666(18) Uani d . 1 . .
    Br Br2 0.61945(10) 0.78903(5) 0.54550(7) 0.03742(19) Uani d . 1 . .
    N N1 0.7631(8) 0.4733(4) 0.2958(5) 0.0269(11) Uani d . 1 . .
    N N2 0.4665(11) 0.5923(5) 0.3096(7) 0.0398(14) Uani d D 1 . .
    N N3 0.9054(9) 0.3672(4) 0.5746(5) 0.0291(11) Uani d . 1 . .
    H H3A 0.7799 0.3302 0.5406 0.044 Uiso calc R 1 . .
    H H3B 0.9481 0.3518 0.6651 0.044 Uiso calc R 1 . .
    H H3C 1.0172 0.3496 0.5280 0.044 Uiso calc R 1 . .
    C C1 0.5506(11) 0.5110(5) 0.2454(6) 0.0295(14) Uani d . 1 . .
    C C2 0.4223(13) 0.4609(6) 0.1291(7) 0.0404(17) Uani d . 1 . .
    H H2 0.2766 0.4863 0.0937 0.048 Uiso calc R 1 . .
    C C3 0.5050(15) 0.3772(7) 0.0677(7) 0.052(2) Uani d . 1 . .
    H H3 0.4149 0.3427 -0.0072 0.062 Uiso calc R 1 . .
    C C4 0.7331(15) 0.3408(7) 0.1176(8) 0.052(2) Uani d . 1 . .
    H H4 0.7975 0.2856 0.0725 0.062 Uiso calc R 1 . .
    C C5 0.8497(13) 0.3880(6) 0.2301(7) 0.0378(16) Uani d . 1 . .
    H H5 0.9953 0.3628 0.2661 0.045 Uiso calc R 1 . .
    C C6 0.9101(11) 0.5224(6) 0.4176(7) 0.0314(14) Uani d . 1 . .
    H H6A 0.8922 0.5998 0.4119 0.038 Uiso calc R 1 . .
    H H6B 1.0686 0.5060 0.4131 0.038 Uiso calc R 1 . .
    C C7 0.8569(10) 0.4843(5) 0.5581(6) 0.0274(13) Uani d . 1 . .
    H H7 0.6928 0.4945 0.5567 0.033 Uiso calc R 1 . .
    C C8 0.9855(11) 0.5495(6) 0.6818(7) 0.0369(16) Uani d . 1 . .
    H H8 0.9549 0.6256 0.6605 0.044 Uiso calc R 1 . .
    C C9 0.8975(15) 0.5251(8) 0.8154(7) 0.057(2) Uani d . 1 . .
    H H9A 0.9414 0.4535 0.8456 0.086 Uiso calc R 1 . .
    H H9B 0.7338 0.5309 0.7994 0.086 Uiso calc R 1 . .
    H H9C 0.9614 0.5753 0.8867 0.086 Uiso calc R 1 . .
    C C10 1.2447(12) 0.5333(8) 0.6994(8) 0.057(2) Uani d . 1 . .
    H H10A 1.3194 0.5787 0.7734 0.086 Uiso calc R 1 . .
    H H10B 1.2962 0.5514 0.6135 0.086 Uiso calc R 1 . .
    H H10C 1.2809 0.4596 0.7224 0.086 Uiso calc R 1 . .
    H H2A 0.355(12) 0.623(8) 0.260(9) 0.09(4) Uiso d D 1 . .
    H H2B 0.525(13) 0.636(6) 0.371(7) 0.06(3) Uiso d D 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 0.0508(4) 0.0348(4) 0.0231(3) -0.0033(3) 0.0026(3) -0.0009(3)
    Br2 0.0309(3) 0.0355(4) 0.0448(4) 0.0023(3) 0.0033(3) -0.0065(3)
    N1 0.033(3) 0.025(3) 0.024(3) 0.001(2) 0.007(2) 0.004(2)
    N2 0.040(4) 0.035(4) 0.041(4) 0.006(3) -0.002(3) -0.003(3)
    N3 0.032(3) 0.029(3) 0.026(3) -0.004(2) 0.004(2) 0.003(2)
    C1 0.041(4) 0.028(4) 0.018(3) -0.001(3) 0.002(3) 0.006(3)
    C2 0.042(4) 0.051(5) 0.025(3) -0.004(3) -0.005(3) 0.006(3)
    C3 0.074(5) 0.054(5) 0.025(4) -0.011(4) -0.002(4) -0.012(4)
    C4 0.077(6) 0.049(5) 0.032(4) 0.006(4) 0.014(4) -0.010(3)
    C5 0.051(4) 0.038(4) 0.026(4) 0.009(3) 0.012(3) 0.003(3)
    C6 0.031(3) 0.032(4) 0.028(3) -0.003(3) -0.004(3) 0.001(3)
    C7 0.021(3) 0.030(3) 0.029(3) 0.001(2) -0.001(2) 0.003(3)
    C8 0.046(4) 0.030(4) 0.031(4) 0.002(3) -0.004(3) -0.006(3)
    C9 0.066(5) 0.077(6) 0.025(4) 0.014(5) -0.003(4) -0.015(4)
    C10 0.035(4) 0.088(7) 0.043(5) -0.016(4) -0.008(3) -0.014(5)
_geom_special_details
;
;
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 H3B . 2.4578 ?
    Br2 H2B . 2.55(7) ?
    N1 C1 . 1.356(8) ?
    N1 C5 . 1.380(8) ?
    N1 C6 . 1.476(8) ?
    N2 C1 . 1.329(9) ?
    N2 H2A . 0.84(8) ?
    N2 H2B . 0.84(7) ?
    N3 C7 . 1.490(8) ?
    N3 H3A . 0.8900 ?
    N3 H3B . 0.8900 ?
    N3 H3C . 0.8900 ?
    C1 C2 . 1.396(9) ?
    C2 C3 . 1.334(11) ?
    C2 H2 . 0.9300 ?
    C3 C4 . 1.431(11) ?
    C3 H3 . 0.9300 ?
    C4 C5 . 1.325(10) ?
    C4 H4 . 0.9300 ?
    C5 H5 . 0.9300 ?
    C6 C7 . 1.523(9) ?
    C6 H6A . 0.9700 ?
    C6 H6B . 0.9700 ?
    C7 C8 . 1.538(9) ?
    C7 H7 . 0.9800 ?
    C8 C9 . 1.506(11) ?
    C8 C10 . 1.531(10) ?
    C8 H8 . 0.9800 ?
    C9 H9A . 0.9600 ?
    C9 H9B . 0.9600 ?
    C9 H9C . 0.9600 ?
    C10 H10A . 0.9600 ?
    C10 H10B . 0.9600 ?
    C10 H10C . 0.9600 ?
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
    C1 N1 C5 . . 119.8(6) ?
    C1 N1 C6 . . 122.1(5) ?
    C5 N1 C6 . . 118.2(5) ?
    C1 N2 H2A . . 114(7) ?
    C1 N2 H2B . . 133(6) ?
    H2A N2 H2B . . 107(9) ?
    C7 N3 H3A . . 109.5 ?
    C7 N3 H3B . . 109.5 ?
    H3A N3 H3B . . 109.5 ?
    C7 N3 H3C . . 109.5 ?
    H3A N3 H3C . . 109.5 ?
    H3B N3 H3C . . 109.5 ?
    N2 C1 N1 . . 119.7(6) ?
    N2 C1 C2 . . 121.4(7) ?
    N1 C1 C2 . . 118.8(7) ?
    C3 C2 C1 . . 121.2(7) ?
    C3 C2 H2 . . 119.4 ?
    C1 C2 H2 . . 119.4 ?
    C2 C3 C4 . . 119.7(7) ?
    C2 C3 H3 . . 120.2 ?
    C4 C3 H3 . . 120.2 ?
    C5 C4 C3 . . 117.9(7) ?
    C5 C4 H4 . . 121.0 ?
    C3 C4 H4 . . 121.0 ?
    C4 C5 N1 . . 122.5(7) ?
    C4 C5 H5 . . 118.7 ?
    N1 C5 H5 . . 118.7 ?
    N1 C6 C7 . . 113.7(5) ?
    N1 C6 H6A . . 108.8 ?
    C7 C6 H6A . . 108.8 ?
    N1 C6 H6B . . 108.8 ?
    C7 C6 H6B . . 108.8 ?
    H6A C6 H6B . . 107.7 ?
    N3 C7 C6 . . 109.6(5) ?
    N3 C7 C8 . . 111.9(5) ?
    C6 C7 C8 . . 112.3(6) ?
    N3 C7 H7 . . 107.6 ?
    C6 C7 H7 . . 107.6 ?
    C8 C7 H7 . . 107.6 ?
    C9 C8 C10 . . 111.4(6) ?
    C9 C8 C7 . . 111.3(6) ?
    C10 C8 C7 . . 111.9(6) ?
    C9 C8 H8 . . 107.3 ?
    C10 C8 H8 . . 107.3 ?
    C7 C8 H8 . . 107.3 ?
    C8 C9 H9A . . 109.5 ?
    C8 C9 H9B . . 109.5 ?
    H9A C9 H9B . . 109.5 ?
    C8 C9 H9C . . 109.5 ?
    H9A C9 H9C . . 109.5 ?
    H9B C9 H9C . . 109.5 ?
    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_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
    C5 N1 C1 N2 . . . . 179.3(6) ?
    C6 N1 C1 N2 . . . . -2.4(9) ?
    C5 N1 C1 C2 . . . . 1.2(8) ?
    C6 N1 C1 C2 . . . . 179.5(6) ?
    N2 C1 C2 C3 . . . . -177.9(7) ?
    N1 C1 C2 C3 . . . . 0.2(10) ?
    C1 C2 C3 C4 . . . . -2.8(11) ?
    C2 C3 C4 C5 . . . . 4.2(11) ?
    C3 C4 C5 N1 . . . . -3.0(11) ?
    C1 N1 C5 C4 . . . . 0.3(10) ?
    C6 N1 C5 C4 . . . . -178.0(7) ?
    C1 N1 C6 C7 . . . . 82.3(7) ?
    C5 N1 C6 C7 . . . . -99.4(7) ?
    N1 C6 C7 N3 . . . . 64.0(7) ?
    N1 C6 C7 C8 . . . . -170.9(5) ?
    N3 C7 C8 C9 . . . . -67.1(7) ?
    C6 C7 C8 C9 . . . . 169.2(6) ?
    N3 C7 C8 C10 . . . . 58.3(8) ?
    C6 C7 C8 C10 . . . . -65.5(8) ?
loop_
    _geom_hbond_atom_site_label_D
    _geom_hbond_atom_site_label_H
    _geom_hbond_atom_site_label_A
    _geom_hbond_site_symmetry_A
    _geom_hbond_distance_DH
    _geom_hbond_distance_HA
    _geom_hbond_distance_DA
    _geom_hbond_angle_DHA
    N2 H2B Br2 . 0.84(7) 2.55(7) 3.368(7) 167(8)
    N2 H2A Br1 2_656 0.84(8) 2.53(8) 3.357(6) 168(10)
    N3 H3C Br2 2_746 0.89 2.50 3.369(5) 166.2
    N3 H3B Br1 . 0.89 2.46 3.238(5) 146.6
    N3 H3A Br2 2_646 0.89 2.43 3.281(5) 160.4
    C3 H3 Br1 1_454 0.93 3.02 3.892(8) 156.9
    C4 H4 Br1 1_554 0.93 2.91 3.748(8) 150.2
    C6 H6A Br1 2_756 0.97 2.96 3.528(7) 118.5
    C5 H5 Br2 2_746 0.93 2.83 3.721(7) 161.9
    C8 H8 Br2 . 0.98 2.93 3.793(7) 147.2
