# Electronic Supplementary Material (ESI) for CrystEngComm
# This journal is © The Royal Society of Chemistry 2012


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#  This CIF contains data from an original supplementary publication 
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#  experimental, refinement, atomic coordinates, 
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#  as required by the journal to which it was submitted. 
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data_[(4-AP)2H]BF4
_database_code_depnum_ccdc_archive 'CCDC 857668'
#TrackingRef '8586_web_deposit_cif_file_0_JayR.Stork_1323458963.4-aminopyridinium.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            '4-aminopyridinium hemi(tetrafluoroborate)'
_chemical_melting_point          ?
_chemical_formula_moiety         'C5 H7 N2, C5 H6 N2, B F4'
_chemical_formula_sum            'C10 H13 B F4 N4'
_chemical_formula_weight         276.05

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'
B B 0.0013 0.0007 '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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'

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'

_cell_length_a                   15.107(2)
_cell_length_b                   9.1347(14)
_cell_length_c                   19.186(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.090(2)
_cell_angle_gamma                90.00
_cell_volume                     2606.7(7)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4498
_cell_measurement_theta_min      2.74
_cell_measurement_theta_max      28.2

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.41
_exptl_crystal_size_min          0.25
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.407
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1136
_exptl_absorpt_coefficient_mu    0.127
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9334
_exptl_absorpt_correction_T_max  0.9689
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2008)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker SMART Apex'
_diffrn_measurement_method       \w
_diffrn_detector_area_resol_mean 8.3
_diffrn_reflns_number            23914
_diffrn_reflns_av_R_equivalents  0.0290
_diffrn_reflns_av_sigmaI/netI    0.0328
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         1.37
_diffrn_reflns_theta_max         30.32
_reflns_number_total             7564
_reflns_number_gt                5021
_reflns_threshold_expression     >2\s(I)

_computing_data_collection       'Apex2 (Bruker, 2009)'
_computing_cell_refinement       'SAINT (Bruker, 2008)'
_computing_data_reduction        'SAINT (Bruker, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.

All H atoms were located in a difference map. C-H protons were placed in
calculated positions. The positions of N-H protons were allowed to refine.

Only one good position was found for the pyridinium H atoms.

Three F atoms of one tetrafluoroborate anion were disordered over three
positions with assumed occupancies of 43 %, 35% and 22 %.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0452P)^2^+0.7831P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         7564
_refine_ls_number_parameters     427
_refine_ls_number_restraints     8
_refine_ls_R_factor_all          0.0817
_refine_ls_R_factor_gt           0.0472
_refine_ls_wR_factor_ref         0.1232
_refine_ls_wR_factor_gt          0.1077
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.053
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.09994(10) 0.49016(18) 0.13877(8) 0.0357(3) Uani 1 1 d . . .
H1 H 0.1286 0.5607 0.1715 0.043 Uiso 1 1 calc R . .
C2 C 0.01071(10) 0.50402(17) 0.11296(8) 0.0343(3) Uani 1 1 d . . .
H2 H -0.0225 0.5826 0.1281 0.041 Uiso 1 1 calc R . .
C3 C -0.03229(9) 0.40151(17) 0.06374(7) 0.0309(3) Uani 1 1 d . . .
C4 C 0.02052(10) 0.28620(16) 0.04425(7) 0.0303(3) Uani 1 1 d . . .
H4 H -0.0058 0.2140 0.0114 0.036 Uiso 1 1 calc R . .
C5 C 0.10917(10) 0.27911(17) 0.07273(7) 0.0323(3) Uani 1 1 d . . .
H5 H 0.1442 0.2010 0.0594 0.039 Uiso 1 1 calc R . .
C6 C 0.37027(11) 0.28546(19) 0.21478(8) 0.0379(4) Uani 1 1 d . . .
H6 H 0.3365 0.2222 0.2394 0.046 Uiso 1 1 calc R . .
C7 C 0.46193(10) 0.28357(18) 0.23316(8) 0.0364(3) Uani 1 1 d . . .
H7 H 0.4903 0.2214 0.2701 0.044 Uiso 1 1 calc R . .
C8 C 0.51352(10) 0.37363(17) 0.19720(8) 0.0339(3) Uani 1 1 d . . .
C9 C 0.46709(11) 0.46303(17) 0.14419(9) 0.0387(4) Uani 1 1 d . . .
H9 H 0.4989 0.5266 0.1181 0.046 Uiso 1 1 calc R . .
C10 C 0.37532(11) 0.45818(17) 0.13023(9) 0.0396(4) Uani 1 1 d . . .
H10 H 0.3450 0.5206 0.0942 0.048 Uiso 1 1 calc R . .
C11 C 0.63080(10) 0.20411(18) 0.04470(8) 0.0363(4) Uani 1 1 d . . .
H11 H 0.6679 0.2636 0.0211 0.044 Uiso 1 1 calc R . .
C12 C 0.54002(9) 0.21590(17) 0.02673(7) 0.0310(3) Uani 1 1 d . . .
H12 H 0.5142 0.2829 -0.0090 0.037 Uiso 1 1 calc R . .
C13 C 0.48435(9) 0.12839(15) 0.06124(7) 0.0248(3) Uani 1 1 d . . .
C14 C 0.52682(9) 0.03135(15) 0.11345(7) 0.0281(3) Uani 1 1 d . . .
H14 H 0.4919 -0.0299 0.1381 0.034 Uiso 1 1 calc R . .
C15 C 0.61809(10) 0.02557(17) 0.12842(8) 0.0328(3) Uani 1 1 d . . .
H15 H 0.6463 -0.0406 0.1637 0.039 Uiso 1 1 calc R . .
C16 C 0.90236(10) -0.01464(17) 0.11799(8) 0.0328(3) Uani 1 1 d . . .
H16 H 0.8764 -0.0851 0.0841 0.039 Uiso 1 1 calc R . .
C17 C 0.99176(9) -0.02827(16) 0.14612(7) 0.0294(3) Uani 1 1 d . . .
H17 H 1.0264 -0.1053 0.1312 0.035 Uiso 1 1 calc R . .
C18 C 1.03156(9) 0.07287(16) 0.19720(7) 0.0279(3) Uani 1 1 d . . .
C19 C 0.97653(10) 0.18447(16) 0.21503(7) 0.0301(3) Uani 1 1 d . . .
H19 H 1.0003 0.2565 0.2489 0.036 Uiso 1 1 calc R . .
C20 C 0.88797(10) 0.18942(17) 0.18333(8) 0.0332(3) Uani 1 1 d . . .
H20 H 0.8518 0.2666 0.1961 0.040 Uiso 1 1 calc R . .
N1 N 0.14890(8) 0.37933(14) 0.11924(7) 0.0337(3) Uani 1 1 d . . .
H1A H 0.2151(12) 0.3751(18) 0.1377(9) 0.040 Uiso 1 1 d . . .
N2 N -0.11962(9) 0.41234(18) 0.03605(8) 0.0404(3) Uani 1 1 d . . .
H2A H -0.1511(12) 0.482(2) 0.0503(10) 0.049 Uiso 1 1 d . . .
H2B H -0.1456(12) 0.349(2) 0.0057(10) 0.049 Uiso 1 1 d . . .
N3 N 0.32529(8) 0.37150(15) 0.16395(7) 0.0363(3) Uani 1 1 d . . .
N4 N 0.60431(10) 0.37437(19) 0.21235(9) 0.0480(4) Uani 1 1 d . . .
H4A H 0.6361(13) 0.430(2) 0.1867(11) 0.058 Uiso 1 1 d . . .
H4B H 0.6262(13) 0.320(2) 0.2481(11) 0.058 Uiso 1 1 d . . .
N5 N 0.66940(8) 0.11076(15) 0.09476(7) 0.0345(3) Uani 1 1 d . . .
H5A H 0.7344(12) 0.1071(19) 0.1077(9) 0.041 Uiso 1 1 d . . .
N6 N 0.39482(8) 0.13583(15) 0.04477(7) 0.0298(3) Uani 1 1 d . . .
H6A H 0.3622(11) 0.0831(19) 0.0673(9) 0.036 Uiso 1 1 d . . .
H6B H 0.3708(11) 0.1970(19) 0.0134(9) 0.036 Uiso 1 1 d . . .
N7 N 0.84930(8) 0.09179(15) 0.13530(7) 0.0348(3) Uani 1 1 d . . .
N8 N 1.11895(9) 0.06227(18) 0.22751(8) 0.0404(3) Uani 1 1 d . . .
H8A H 1.1426(12) 0.130(2) 0.2580(10) 0.048 Uiso 1 1 d . . .
H8B H 1.1523(12) -0.005(2) 0.2124(10) 0.048 Uiso 1 1 d . . .
B1 B 0.27716(11) 0.1492(2) 0.39052(9) 0.0328(4) Uani 1 1 d . . .
F1 F 0.23417(6) 0.24082(10) 0.33793(5) 0.0425(2) Uani 1 1 d . . .
F2 F 0.26286(6) 0.00438(10) 0.36903(6) 0.0497(3) Uani 1 1 d . . .
F3 F 0.36807(6) 0.17947(11) 0.40283(6) 0.0520(3) Uani 1 1 d . . .
F4 F 0.24170(8) 0.17342(13) 0.45158(5) 0.0602(3) Uani 1 1 d . . .
B2 B 0.25151(14) 0.8515(2) 0.11711(10) 0.0407(4) Uani 1 1 d D . .
F5 F 0.22123(7) 0.81355(11) 0.17889(5) 0.0483(3) Uani 1 1 d . A .
F6 F 0.3315(6) 0.8013(10) 0.1191(6) 0.060(3) Uani 0.35 1 d P A 1
F7 F 0.2597(5) 1.0107(6) 0.1213(5) 0.0330(14) Uani 0.35 1 d PD A 1
F8 F 0.1930(5) 0.8218(9) 0.0573(4) 0.081(2) Uani 0.35 1 d PD A 1
F9 F 0.2230(3) 0.7364(5) 0.0670(2) 0.0553(10) Uani 0.43 1 d PD A 2
F10 F 0.2335(3) 0.9794(5) 0.0928(2) 0.0639(14) Uani 0.43 1 d PD A 2
F11 F 0.3482(4) 0.8310(9) 0.1269(4) 0.0440(17) Uani 0.43 1 d PD A 2
F12 F 0.1629(7) 0.8756(14) 0.0672(5) 0.073(3) Uani 0.22 1 d PD A 3
F13 F 0.2987(15) 0.7573(16) 0.0942(9) 0.153(10) Uani 0.22 1 d PD A 3
F14 F 0.2744(10) 0.9975(14) 0.1227(9) 0.106(6) Uani 0.22 1 d PD A 3

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 0.0420(8) 0.0350(8) 0.0317(8) -0.0023(6) 0.0106(6) -0.0018(7)
C2 0.0396(8) 0.0328(8) 0.0345(8) 0.0020(6) 0.0170(6) 0.0054(6)
C3 0.0320(7) 0.0349(8) 0.0282(7) 0.0092(6) 0.0121(6) 0.0028(6)
C4 0.0364(7) 0.0298(8) 0.0256(7) 0.0037(6) 0.0080(6) 0.0002(6)
C5 0.0383(8) 0.0295(8) 0.0303(7) 0.0027(6) 0.0094(6) 0.0068(6)
C6 0.0436(8) 0.0424(9) 0.0300(8) -0.0023(7) 0.0125(6) 0.0008(7)
C7 0.0438(8) 0.0399(9) 0.0242(7) -0.0012(6) 0.0026(6) 0.0074(7)
C8 0.0364(8) 0.0316(8) 0.0320(8) -0.0127(6) 0.0014(6) -0.0023(6)
C9 0.0471(9) 0.0266(8) 0.0411(9) -0.0018(7) 0.0041(7) -0.0082(7)
C10 0.0488(9) 0.0258(8) 0.0402(9) -0.0006(7) -0.0032(7) 0.0040(7)
C11 0.0328(7) 0.0486(10) 0.0280(7) -0.0030(7) 0.0073(6) -0.0101(7)
C12 0.0327(7) 0.0348(8) 0.0244(7) 0.0016(6) 0.0021(5) -0.0042(6)
C13 0.0268(6) 0.0244(7) 0.0224(6) -0.0059(5) 0.0025(5) -0.0001(5)
C14 0.0306(7) 0.0251(7) 0.0284(7) -0.0005(6) 0.0045(5) -0.0012(5)
C15 0.0344(7) 0.0291(8) 0.0322(8) -0.0031(6) -0.0017(6) 0.0055(6)
C16 0.0355(7) 0.0327(8) 0.0291(7) -0.0023(6) 0.0024(6) -0.0086(6)
C17 0.0328(7) 0.0270(7) 0.0283(7) 0.0001(6) 0.0044(6) -0.0013(6)
C18 0.0296(7) 0.0323(8) 0.0214(7) 0.0050(5) 0.0031(5) -0.0052(6)
C19 0.0369(7) 0.0319(8) 0.0218(7) -0.0010(6) 0.0062(6) -0.0063(6)
C20 0.0356(7) 0.0351(8) 0.0305(8) 0.0010(6) 0.0099(6) 0.0013(6)
N1 0.0316(6) 0.0370(7) 0.0323(7) 0.0014(5) 0.0050(5) 0.0028(5)
N2 0.0311(7) 0.0505(9) 0.0416(8) 0.0075(7) 0.0117(6) 0.0056(6)
N3 0.0347(7) 0.0364(7) 0.0367(7) -0.0067(6) 0.0032(5) 0.0050(5)
N4 0.0384(8) 0.0535(10) 0.0490(9) -0.0107(7) -0.0010(7) -0.0066(7)
N5 0.0250(6) 0.0449(8) 0.0324(7) -0.0089(6) 0.0022(5) 0.0006(5)
N6 0.0261(6) 0.0319(7) 0.0302(7) 0.0005(5) 0.0016(5) 0.0015(5)
N7 0.0292(6) 0.0411(8) 0.0333(7) 0.0005(6) 0.0031(5) -0.0028(5)
N8 0.0315(7) 0.0510(9) 0.0351(7) -0.0038(6) -0.0042(6) -0.0009(6)
B1 0.0293(8) 0.0337(9) 0.0336(9) -0.0034(7) 0.0006(7) -0.0051(7)
F1 0.0390(5) 0.0399(5) 0.0451(5) -0.0013(4) -0.0028(4) 0.0015(4)
F2 0.0461(5) 0.0309(5) 0.0675(7) -0.0056(5) -0.0028(5) -0.0064(4)
F3 0.0277(5) 0.0460(6) 0.0769(7) -0.0058(5) -0.0056(5) -0.0045(4)
F4 0.0739(7) 0.0684(8) 0.0424(6) -0.0054(5) 0.0211(5) -0.0136(6)
B2 0.0478(11) 0.0406(11) 0.0334(10) 0.0003(8) 0.0062(8) -0.0148(9)
F5 0.0570(6) 0.0474(6) 0.0443(6) 0.0049(5) 0.0197(5) -0.0084(5)
F6 0.098(7) 0.023(4) 0.073(7) 0.002(3) 0.053(6) 0.029(4)
F7 0.036(2) 0.018(2) 0.050(4) 0.002(2) 0.021(3) 0.007(2)
F8 0.091(6) 0.091(6) 0.051(3) -0.028(4) -0.015(4) -0.034(4)
F9 0.053(2) 0.064(3) 0.0476(18) -0.0176(18) 0.0056(16) -0.024(2)
F10 0.084(4) 0.043(2) 0.072(3) 0.023(2) 0.033(2) 0.025(2)
F11 0.0253(13) 0.066(5) 0.0403(19) 0.002(2) 0.0045(12) -0.0093(19)
F12 0.069(5) 0.105(9) 0.038(4) 0.000(4) -0.009(3) 0.006(5)
F13 0.30(3) 0.073(12) 0.126(16) 0.036(9) 0.142(18) 0.105(15)
F14 0.134(11) 0.126(11) 0.054(8) 0.013(7) 0.006(7) -0.075(8)

_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.345(2) . ?
C1 C2 1.358(2) . ?
C1 H1 0.9500 . ?
C2 C3 1.406(2) . ?
C2 H2 0.9500 . ?
C3 N2 1.3368(19) . ?
C3 C4 1.411(2) . ?
C4 C5 1.356(2) . ?
C4 H4 0.9500 . ?
C5 N1 1.344(2) . ?
C5 H5 0.9500 . ?
C6 N3 1.341(2) . ?
C6 C7 1.368(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.396(2) . ?
C7 H7 0.9500 . ?
C8 N4 1.351(2) . ?
C8 C9 1.394(2) . ?
C9 C10 1.366(2) . ?
C9 H9 0.9500 . ?
C10 N3 1.337(2) . ?
C10 H10 0.9500 . ?
C11 N5 1.339(2) . ?
C11 C12 1.359(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.4070(19) . ?
C12 H12 0.9500 . ?
C13 N6 1.3358(17) . ?
C13 C14 1.4055(19) . ?
C14 C15 1.3594(19) . ?
C14 H14 0.9500 . ?
C15 N5 1.341(2) . ?
C15 H15 0.9500 . ?
C16 N7 1.338(2) . ?
C16 C17 1.369(2) . ?
C16 H16 0.9500 . ?
C17 C18 1.4032(19) . ?
C17 H17 0.9500 . ?
C18 N8 1.3495(18) . ?
C18 C19 1.395(2) . ?
C19 C20 1.370(2) . ?
C19 H19 0.9500 . ?
C20 N7 1.3405(19) . ?
C20 H20 0.9500 . ?
N1 H1A 1.002(17) . ?
N2 H2A 0.87(2) . ?
N2 H2B 0.865(19) . ?
N4 H4A 0.90(2) . ?
N4 H4B 0.87(2) . ?
N5 H5A 0.971(17) . ?
N6 H6A 0.858(17) . ?
N6 H6B 0.855(17) . ?
N8 H8A 0.882(19) . ?
N8 H8B 0.88(2) . ?
B1 F3 1.3802(18) . ?
B1 F1 1.382(2) . ?
B1 F4 1.389(2) . ?
B1 F2 1.391(2) . ?
B2 F13 1.245(12) . ?
B2 F10 1.270(5) . ?
B2 F6 1.287(9) . ?
B2 F8 1.347(6) . ?
B2 F14 1.377(13) . ?
B2 F5 1.387(2) . ?
B2 F9 1.438(4) . ?
B2 F11 1.452(6) . ?
B2 F7 1.461(6) . ?
B2 F12 1.520(10) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C2 121.85(15) . . ?
N1 C1 H1 119.1 . . ?
C2 C1 H1 119.1 . . ?
C1 C2 C3 119.69(14) . . ?
C1 C2 H2 120.2 . . ?
C3 C2 H2 120.2 . . ?
N2 C3 C2 121.70(14) . . ?
N2 C3 C4 120.96(15) . . ?
C2 C3 C4 117.33(13) . . ?
C5 C4 C3 119.55(14) . . ?
C5 C4 H4 120.2 . . ?
C3 C4 H4 120.2 . . ?
N1 C5 C4 121.96(14) . . ?
N1 C5 H5 119.0 . . ?
C4 C5 H5 119.0 . . ?
N3 C6 C7 123.78(15) . . ?
N3 C6 H6 118.1 . . ?
C7 C6 H6 118.1 . . ?
C6 C7 C8 119.52(14) . . ?
C6 C7 H7 120.2 . . ?
C8 C7 H7 120.2 . . ?
N4 C8 C9 121.07(16) . . ?
N4 C8 C7 122.02(16) . . ?
C9 C8 C7 116.92(14) . . ?
C10 C9 C8 119.19(15) . . ?
C10 C9 H9 120.4 . . ?
C8 C9 H9 120.4 . . ?
N3 C10 C9 124.38(15) . . ?
N3 C10 H10 117.8 . . ?
C9 C10 H10 117.8 . . ?
N5 C11 C12 121.72(14) . . ?
N5 C11 H11 119.1 . . ?
C12 C11 H11 119.1 . . ?
C11 C12 C13 119.71(14) . . ?
C11 C12 H12 120.1 . . ?
C13 C12 H12 120.1 . . ?
N6 C13 C14 121.17(13) . . ?
N6 C13 C12 121.58(13) . . ?
C14 C13 C12 117.25(12) . . ?
C15 C14 C13 119.64(13) . . ?
C15 C14 H14 120.2 . . ?
C13 C14 H14 120.2 . . ?
N5 C15 C14 121.74(14) . . ?
N5 C15 H15 119.1 . . ?
C14 C15 H15 119.1 . . ?
N7 C16 C17 124.08(14) . . ?
N7 C16 H16 118.0 . . ?
C17 C16 H16 118.0 . . ?
C16 C17 C18 119.19(14) . . ?
C16 C17 H17 120.4 . . ?
C18 C17 H17 120.4 . . ?
N8 C18 C19 121.78(14) . . ?
N8 C18 C17 121.39(14) . . ?
C19 C18 C17 116.83(12) . . ?
C20 C19 C18 119.52(13) . . ?
C20 C19 H19 120.2 . . ?
C18 C19 H19 120.2 . . ?
N7 C20 C19 123.87(14) . . ?
N7 C20 H20 118.1 . . ?
C19 C20 H20 118.1 . . ?
C5 N1 C1 119.61(13) . . ?
C5 N1 H1A 120.7(10) . . ?
C1 N1 H1A 119.6(10) . . ?
C3 N2 H2A 119.0(12) . . ?
C3 N2 H2B 121.1(13) . . ?
H2A N2 H2B 119.8(17) . . ?
C10 N3 C6 116.20(13) . . ?
C8 N4 H4A 120.2(13) . . ?
C8 N4 H4B 113.5(14) . . ?
H4A N4 H4B 126.2(19) . . ?
C11 N5 C15 119.93(13) . . ?
C11 N5 H5A 120.0(10) . . ?
C15 N5 H5A 120.1(10) . . ?
C13 N6 H6A 119.9(11) . . ?
C13 N6 H6B 119.1(11) . . ?
H6A N6 H6B 120.9(15) . . ?
C16 N7 C20 116.49(12) . . ?
C18 N8 H8A 119.2(12) . . ?
C18 N8 H8B 118.9(12) . . ?
H8A N8 H8B 121.5(17) . . ?
F3 B1 F1 109.26(13) . . ?
F3 B1 F4 110.06(13) . . ?
F1 B1 F4 108.54(14) . . ?
F3 B1 F2 109.85(13) . . ?
F1 B1 F2 109.32(13) . . ?
F4 B1 F2 109.80(14) . . ?
F13 B2 F10 127.2(9) . . ?
F10 B2 F6 118.6(5) . . ?
F13 B2 F8 83.7(10) . . ?
F10 B2 F8 78.8(4) . . ?
F6 B2 F8 115.2(6) . . ?
F13 B2 F14 123.1(12) . . ?
F6 B2 F14 97.0(8) . . ?
F8 B2 F14 112.3(8) . . ?
F13 B2 F5 115.0(8) . . ?
F10 B2 F5 117.6(3) . . ?
F6 B2 F5 109.5(6) . . ?
F8 B2 F5 114.3(4) . . ?
F14 B2 F5 106.9(7) . . ?
F13 B2 F9 51.8(10) . . ?
F10 B2 F9 114.0(3) . . ?
F6 B2 F9 85.9(4) . . ?
F14 B2 F9 143.2(7) . . ?
F5 B2 F9 106.5(2) . . ?
F13 B2 F11 48.1(12) . . ?
F10 B2 F11 108.2(4) . . ?
F8 B2 F11 125.4(5) . . ?
F14 B2 F11 83.2(7) . . ?
F5 B2 F11 109.4(4) . . ?
F9 B2 F11 99.7(4) . . ?
F13 B2 F7 131.2(10) . . ?
F6 B2 F7 106.4(5) . . ?
F8 B2 F7 106.5(5) . . ?
F5 B2 F7 103.9(3) . . ?
F9 B2 F7 141.0(4) . . ?
F11 B2 F7 92.7(4) . . ?
F13 B2 F12 111.9(10) . . ?
F10 B2 F12 61.8(6) . . ?
F6 B2 F12 142.1(6) . . ?
F14 B2 F12 95.2(8) . . ?
F5 B2 F12 100.9(5) . . ?
F9 B2 F12 63.7(4) . . ?
F11 B2 F12 148.8(5) . . ?
F7 B2 F12 87.0(6) . . ?

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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 C3 -0.8(2) . . . . ?
C1 C2 C3 N2 -178.84(14) . . . . ?
C1 C2 C3 C4 0.9(2) . . . . ?
N2 C3 C4 C5 179.31(14) . . . . ?
C2 C3 C4 C5 -0.4(2) . . . . ?
C3 C4 C5 N1 -0.1(2) . . . . ?
N3 C6 C7 C8 -1.0(2) . . . . ?
C6 C7 C8 N4 -178.86(15) . . . . ?
C6 C7 C8 C9 0.8(2) . . . . ?
N4 C8 C9 C10 179.55(15) . . . . ?
C7 C8 C9 C10 -0.1(2) . . . . ?
C8 C9 C10 N3 -0.5(2) . . . . ?
N5 C11 C12 C13 0.0(2) . . . . ?
C11 C12 C13 N6 -179.48(14) . . . . ?
C11 C12 C13 C14 -0.1(2) . . . . ?
N6 C13 C14 C15 179.37(13) . . . . ?
C12 C13 C14 C15 0.0(2) . . . . ?
C13 C14 C15 N5 0.2(2) . . . . ?
N7 C16 C17 C18 1.0(2) . . . . ?
C16 C17 C18 N8 178.65(14) . . . . ?
C16 C17 C18 C19 -1.3(2) . . . . ?
N8 C18 C19 C20 -179.24(14) . . . . ?
C17 C18 C19 C20 0.8(2) . . . . ?
C18 C19 C20 N7 0.2(2) . . . . ?
C4 C5 N1 C1 0.3(2) . . . . ?
C2 C1 N1 C5 0.2(2) . . . . ?
C9 C10 N3 C6 0.3(2) . . . . ?
C7 C6 N3 C10 0.4(2) . . . . ?
C12 C11 N5 C15 0.2(2) . . . . ?
C14 C15 N5 C11 -0.3(2) . . . . ?
C17 C16 N7 C20 0.0(2) . . . . ?
C19 C20 N7 C16 -0.6(2) . . . . ?

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
N1 H1A N3 1.002(17) 1.652(17) 2.6535(18) 177.0(15) .
N2 H2A F4 0.87(2) 2.21(2) 3.0493(19) 161.0(17) 2
N2 H2A F2 0.87(2) 2.490(19) 3.1759(18) 136.2(16) 2
N2 H2B F9 0.865(19) 1.83(2) 2.668(4) 162.1(18) 3_565
N2 H2B F8 0.865(19) 2.03(2) 2.884(6) 171.3(18) 3_565
N2 H2B F12 0.865(19) 2.47(2) 3.288(12) 158.1(17) 3_565
N4 H4A F2 0.90(2) 2.12(2) 2.996(2) 162.6(18) 2_655
N4 H4B F11 0.87(2) 2.36(2) 3.067(8) 138.7(18) 2_645
N4 H4B F5 0.87(2) 2.48(2) 3.1116(19) 130.4(17) 2_645
N4 H4B F6 0.87(2) 2.52(2) 3.277(12) 146.5(18) 2_645
N5 H5A N7 0.971(17) 1.729(17) 2.6982(17) 176.0(16) .
N6 H6A F14 0.858(17) 2.00(2) 2.845(14) 168.7(16) 1_545
N6 H6A F7 0.858(17) 2.115(19) 2.946(6) 163.1(16) 1_545
N6 H6A F10 0.858(17) 2.292(18) 3.101(5) 157.4(15) 1_545
N6 H6A F11 0.858(17) 2.60(2) 3.335(9) 144.9(14) 1_545
N6 H6B F3 0.855(17) 2.396(18) 3.1686(18) 150.6(14) 4_565
N6 H6B F4 0.855(17) 2.408(17) 3.1834(17) 151.1(14) 4_565
N8 H8A F1 0.882(19) 2.13(2) 2.9809(17) 161.0(17) 1_655
N8 H8B F5 0.88(2) 2.11(2) 2.987(2) 173.1(18) 1_645
N8 H8B F7 0.88(2) 2.59(2) 3.228(6) 130.3(16) 1_645

_diffrn_measured_fraction_theta_max 0.966
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.566
_refine_diff_density_min         -0.416
_refine_diff_density_rms         0.042


data_[(4-AP)2H]PF6
_database_code_depnum_ccdc_archive 'CCDC 857669'
#TrackingRef '8586_web_deposit_cif_file_0_JayR.Stork_1323458963.4-aminopyridinium.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            '4-aminopyridinium hemihexafluorphosphate'
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H13 N4, F6 P'
_chemical_formula_sum            'C10 H13 F6 N4 P'
_chemical_formula_weight         334.21

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           tetragonal
_symmetry_space_group_name_H-M   'I 41/a m d'
_symmetry_space_group_name_Hall  '-I 4bd 2'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y+1/2, z'
'x, -y, -z'
'-x, y+1/2, -z'
'-y+1/4, -x+1/4, -z+3/4'
'y+1/4, x+3/4, -z+1/4'
'y+1/4, -x+1/4, z+3/4'
'-y+1/4, x+3/4, z+1/4'
'x+1/2, y+1/2, z+1/2'
'-x+1/2, -y+1, z+1/2'
'x+1/2, -y+1/2, -z+1/2'
'-x+1/2, y+1, -z+1/2'
'-y+3/4, -x+3/4, -z+5/4'
'y+3/4, x+5/4, -z+3/4'
'y+3/4, -x+3/4, z+5/4'
'-y+3/4, x+5/4, z+3/4'
'-x, -y, -z'
'x, y-1/2, -z'
'-x, y, z'
'x, -y-1/2, z'
'y-1/4, x-1/4, z-3/4'
'-y-1/4, -x-3/4, z-1/4'
'-y-1/4, x-1/4, -z-3/4'
'y-1/4, -x-3/4, -z-1/4'
'-x+1/2, -y+1/2, -z+1/2'
'x+1/2, y, -z+1/2'
'-x+1/2, y+1/2, z+1/2'
'x+1/2, -y, z+1/2'
'y+1/4, x+1/4, z-1/4'
'-y+1/4, -x-1/4, z+1/4'
'-y+1/4, x+1/4, -z-1/4'
'y+1/4, -x-1/4, -z+1/4'

_cell_length_a                   6.6040(10)
_cell_length_b                   6.6040(10)
_cell_length_c                   31.614(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1378.8(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    817
_cell_measurement_theta_min      3.64
_cell_measurement_theta_max      30.7

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.610
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             680
_exptl_absorpt_coefficient_mu    0.267
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9242
_exptl_absorpt_correction_T_max  0.9610
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2008)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker SMART Apex'
_diffrn_measurement_method       \w
_diffrn_detector_area_resol_mean 8.3
_diffrn_reflns_number            2833
_diffrn_reflns_av_R_equivalents  0.0234
_diffrn_reflns_av_sigmaI/netI    0.0165
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -43
_diffrn_reflns_limit_l_max       43
_diffrn_reflns_theta_min         2.58
_diffrn_reflns_theta_max         30.46
_reflns_number_total             603
_reflns_number_gt                517
_reflns_threshold_expression     >2/s(I)

_computing_data_collection       'Apex2 (Bruker, 2009)'
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_computing_structure_solution    SIR2004
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.

All atoms are on special positions.

All H atoms were located in a difference map and were placed in calculated
positions. The position of the amine H atom was allowed to refine.

The pyridyl H atom was disordered over an inversion center, and its occupancy
was set to 12.5 %.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0440P)^2^+1.4228P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         603
_refine_ls_number_parameters     39
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0413
_refine_ls_R_factor_gt           0.0347
_refine_ls_wR_factor_ref         0.0967
_refine_ls_wR_factor_gt          0.0902
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      1.060
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.6743(3) 0.2500 0.56170(6) 0.0298(4) Uani 1 2 d S . .
H1 H 0.7981 0.2500 0.5770 0.036 Uiso 1 2 calc SR . .
C2 C 0.6811(3) 0.2500 0.51838(5) 0.0270(4) Uani 1 2 d S . .
H2 H 0.8076 0.2500 0.5041 0.032 Uiso 1 2 calc SR . .
C3 C 0.5000 0.2500 0.49541(8) 0.0231(5) Uani 1 4 d S . .
N1 N 0.5000 0.2500 0.45267(7) 0.0318(5) Uani 1 4 d S . .
H1A H 0.382(4) 0.2500 0.4400(8) 0.038 Uiso 1 2 d S . .
N2 N 0.5000 0.2500 0.58326(7) 0.0304(5) Uani 1 4 d S . .
H2A H 0.5000 0.2500 0.6111 0.037 Uiso 0.50 4 calc SPR A -1
P1 P 0.0000 0.2500 0.3750 0.0189(2) Uani 1 8 d S . .
F1 F 0.24069(19) 0.2500 0.37513(4) 0.0495(4) Uani 1 2 d S . .
F2 F 0.0000 0.2500 0.32426(5) 0.0307(4) Uani 1 4 d S . .

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 0.0257(9) 0.0385(10) 0.0251(9) 0.000 -0.0066(7) 0.000
C2 0.0189(7) 0.0377(9) 0.0244(8) 0.000 0.0029(6) 0.000
C3 0.0238(11) 0.0286(12) 0.0169(10) 0.000 0.000 0.000
N1 0.0390(13) 0.0402(13) 0.0163(10) 0.000 0.000 0.000
N2 0.0376(13) 0.0379(12) 0.0158(9) 0.000 0.000 0.000
P1 0.0216(3) 0.0216(3) 0.0135(4) 0.000 0.000 0.000
F1 0.0215(6) 0.0962(12) 0.0309(7) 0.000 0.0035(5) 0.000
F2 0.0457(10) 0.0328(8) 0.0137(7) 0.000 0.000 0.000

_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N2 1.338(2) . ?
C1 C2 1.370(2) . ?
C1 H1 0.9500 . ?
C2 C3 1.399(2) . ?
C2 H2 0.9500 . ?
C3 N1 1.351(3) . ?
C3 C2 1.399(2) 2_655 ?
N1 H1A 0.88(2) . ?
N2 C1 1.338(2) 2_655 ?
N2 H2A 0.8800 . ?
P1 F1 1.5895(13) . ?
P1 F1 1.5895(13) 2 ?
P1 F1 1.5895(13) 14_445 ?
P1 F1 1.5895(13) 5 ?
P1 F2 1.6038(15) 5 ?
P1 F2 1.6040(15) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 C1 C2 122.49(18) . . ?
N2 C1 H1 118.8 . . ?
C2 C1 H1 118.8 . . ?
C1 C2 C3 119.41(17) . . ?
C1 C2 H2 120.3 . . ?
C3 C2 H2 120.3 . . ?
N1 C3 C2 121.26(11) . 2_655 ?
N1 C3 C2 121.27(11) . . ?
C2 C3 C2 117.5(2) 2_655 . ?
C3 N1 H1A 117.1(16) . . ?
C1 N2 C1 118.7(2) . 2_655 ?
C1 N2 H2A 120.6 . . ?
C1 N2 H2A 120.6 2_655 . ?
F1 P1 F1 179.71(9) . 2 ?
F1 P1 F1 90.000(1) . 14_445 ?
F1 P1 F1 90.0 2 14_445 ?
F1 P1 F1 90.0 . 5 ?
F1 P1 F1 90.000(1) 2 5 ?
F1 P1 F1 179.71(9) 14_445 5 ?
F1 P1 F2 89.86(4) . 5 ?
F1 P1 F2 89.86(4) 2 5 ?
F1 P1 F2 90.15(4) 14_445 5 ?
F1 P1 F2 90.15(4) 5 5 ?
F1 P1 F2 90.14(4) . . ?
F1 P1 F2 90.14(4) 2 . ?
F1 P1 F2 89.85(4) 14_445 . ?
F1 P1 F2 89.85(4) 5 . ?
F2 P1 F2 180.0 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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N2 C1 C2 C3 0.000(1) . . . . ?
C1 C2 C3 N1 180.0 . . . . ?
C1 C2 C3 C2 0.0 . . . 2_655 ?
C2 C1 N2 C1 0.0 . . . 2_655 ?

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
N1 H1A F1 0.88(2) 2.25(2) 2.990(2) 142(2) .
N2 H2A N2 0.88 1.76 2.639(4) 180.0 13

_diffrn_measured_fraction_theta_max 0.982
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.329
_refine_diff_density_min         -0.306
_refine_diff_density_rms         0.052


data_[(4-AP)2H]Cl
_database_code_depnum_ccdc_archive 'CCDC 857670'
#TrackingRef '8586_web_deposit_cif_file_0_JayR.Stork_1323458963.4-aminopyridinium.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            '4-Aminopyridinium hemichloride'
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H13 N4, Cl'
_chemical_formula_sum            'C10 H13 Cl N4'
_chemical_formula_weight         224.69

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   9.7157(17)
_cell_length_b                   8.8484(16)
_cell_length_c                   13.216(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.285(2)
_cell_angle_gamma                90.00
_cell_volume                     1131.3(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3839
_cell_measurement_theta_min      2.50
_cell_measurement_theta_max      31.0

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.31
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.319
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             472
_exptl_absorpt_coefficient_mu    0.311
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8857
_exptl_absorpt_correction_T_max  0.9098
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2008)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker SMART Apex'
_diffrn_measurement_method       \w
_diffrn_detector_area_resol_mean 8.3
_diffrn_reflns_number            12908
_diffrn_reflns_av_R_equivalents  0.0263
_diffrn_reflns_av_sigmaI/netI    0.0246
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.50
_diffrn_reflns_theta_max         31.15
_reflns_number_total             3432
_reflns_number_gt                2869
_reflns_threshold_expression     >2/s(I)

_computing_data_collection       'Apex2 (Bruker, 2009)'
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_computing_structure_solution    SIR2004
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.

All atoms are on special positions.

All H atoms were located in a difference map and were placed in calculated
positions. The positions of the amine and pyridinium H atoms were allowed
to refine.

The pyridinium H atoms were disordered over two positions. Their
occupancies were set to 50 %.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0371P)^2^+0.5730P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3432
_refine_ls_number_parameters     154
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0466
_refine_ls_R_factor_gt           0.0359
_refine_ls_wR_factor_ref         0.0914
_refine_ls_wR_factor_gt          0.0841
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.033
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.46478(13) 0.73062(14) 0.60854(10) 0.0202(2) Uani 1 1 d . . .
H1 H 0.4352 0.8324 0.5993 0.024 Uiso 1 1 calc R . .
C2 C 0.37256(13) 0.62616(14) 0.63841(9) 0.0186(2) Uani 1 1 d . . .
H2 H 0.2809 0.6556 0.6489 0.022 Uiso 1 1 calc R . .
C3 C 0.41463(12) 0.47490(13) 0.65344(9) 0.0162(2) Uani 1 1 d . . .
C4 C 0.55182(13) 0.43911(14) 0.63565(9) 0.0191(2) Uani 1 1 d . . .
H4 H 0.5852 0.3386 0.6447 0.023 Uiso 1 1 calc R . .
C5 C 0.63661(13) 0.55096(15) 0.60506(10) 0.0206(2) Uani 1 1 d . . .
H5 H 0.7285 0.5253 0.5927 0.025 Uiso 1 1 calc R . .
C6 C 0.76781(13) 0.02996(15) 0.62793(10) 0.0227(3) Uani 1 1 d . . .
H6 H 0.7310 0.0056 0.6901 0.027 Uiso 1 1 calc R . .
C7 C 0.84411(13) 0.15934(14) 0.62306(9) 0.0200(2) Uani 1 1 d . . .
H7 H 0.8605 0.2225 0.6811 0.024 Uiso 1 1 calc R . .
C8 C 0.89810(12) 0.19786(13) 0.53121(9) 0.0168(2) Uani 1 1 d . . .
C9 C 0.86909(13) 0.09880(14) 0.44809(9) 0.0181(2) Uani 1 1 d . . .
H9 H 0.9023 0.1209 0.3843 0.022 Uiso 1 1 calc R . .
C10 C 0.79317(13) -0.02867(14) 0.45978(10) 0.0200(2) Uani 1 1 d . . .
H10 H 0.7753 -0.0947 0.4034 0.024 Uiso 1 1 calc R . .
N1 N 0.59547(11) 0.69530(13) 0.59176(8) 0.0209(2) Uani 1 1 d . . .
H1A H 0.646(4) 0.772(4) 0.572(3) 0.025 Uiso 0.50 1 d P A 1
N2 N 0.32668(12) 0.36815(13) 0.68214(9) 0.0211(2) Uani 1 1 d . . .
H2A H 0.3610(17) 0.283(2) 0.7028(12) 0.025 Uiso 1 1 d . . .
H2B H 0.2497(18) 0.3955(19) 0.7001(12) 0.025 Uiso 1 1 d . . .
N3 N 0.74267(11) -0.06431(13) 0.54835(9) 0.0215(2) Uani 1 1 d . . .
H3A H 0.701(4) -0.147(4) 0.559(3) 0.026 Uiso 0.50 1 d P B 2
N4 N 0.97560(13) 0.32198(13) 0.52249(9) 0.0242(2) Uani 1 1 d . . .
H4A H 0.9979(18) 0.347(2) 0.4647(14) 0.029 Uiso 1 1 d . . .
H4B H 0.9927(17) 0.381(2) 0.5750(14) 0.029 Uiso 1 1 d . . .
Cl1 Cl 0.47635(3) 0.05545(3) 0.78294(2) 0.02177(9) 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 0.0222(6) 0.0154(5) 0.0231(6) -0.0006(4) 0.0020(5) 0.0006(4)
C2 0.0178(5) 0.0179(5) 0.0202(5) -0.0009(4) 0.0026(4) 0.0024(4)
C3 0.0186(5) 0.0158(5) 0.0139(5) -0.0009(4) -0.0006(4) -0.0003(4)
C4 0.0192(5) 0.0184(5) 0.0192(5) -0.0007(4) -0.0004(4) 0.0034(4)
C5 0.0167(5) 0.0235(6) 0.0216(6) -0.0013(5) 0.0012(4) 0.0018(4)
C6 0.0203(6) 0.0253(6) 0.0227(6) 0.0030(5) 0.0033(5) 0.0003(5)
C7 0.0220(6) 0.0194(6) 0.0183(5) -0.0022(4) 0.0006(4) 0.0015(5)
C8 0.0170(5) 0.0136(5) 0.0192(5) 0.0006(4) -0.0011(4) 0.0023(4)
C9 0.0207(6) 0.0172(5) 0.0161(5) 0.0004(4) 0.0002(4) 0.0026(4)
C10 0.0196(6) 0.0175(6) 0.0221(6) -0.0028(4) -0.0026(5) 0.0014(4)
N1 0.0197(5) 0.0195(5) 0.0235(5) -0.0002(4) 0.0024(4) -0.0034(4)
N2 0.0214(5) 0.0176(5) 0.0244(5) 0.0036(4) 0.0032(4) 0.0006(4)
N3 0.0180(5) 0.0179(5) 0.0281(6) 0.0019(4) 0.0004(4) -0.0023(4)
N4 0.0330(6) 0.0167(5) 0.0228(5) -0.0003(4) 0.0016(5) -0.0064(4)
Cl1 0.02322(15) 0.02039(15) 0.02244(15) 0.00156(11) 0.00604(11) 0.00374(11)

_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.3458(17) . ?
C1 C2 1.3704(17) . ?
C1 H1 0.9500 . ?
C2 C3 1.4082(17) . ?
C2 H2 0.9500 . ?
C3 N2 1.3513(16) . ?
C3 C4 1.4106(17) . ?
C4 C5 1.3722(18) . ?
C4 H4 0.9500 . ?
C5 N1 1.3449(17) . ?
C5 H5 0.9500 . ?
C6 N3 1.3470(17) . ?
C6 C7 1.3686(18) . ?
C6 H6 0.9500 . ?
C7 C8 1.4079(17) . ?
C7 H7 0.9500 . ?
C8 N4 1.3426(16) . ?
C8 C9 1.4132(17) . ?
C9 C10 1.3642(17) . ?
C9 H9 0.9500 . ?
C10 N3 1.3476(17) . ?
C10 H10 0.9500 . ?
N1 H1A 0.89(4) . ?
N2 H2A 0.858(17) . ?
N2 H2B 0.841(18) . ?
N3 H3A 0.85(4) . ?
N4 H4A 0.843(18) . ?
N4 H4B 0.872(18) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C2 122.87(12) . . ?
N1 C1 H1 118.6 . . ?
C2 C1 H1 118.6 . . ?
C1 C2 C3 119.52(11) . . ?
C1 C2 H2 120.2 . . ?
C3 C2 H2 120.2 . . ?
N2 C3 C2 121.41(11) . . ?
N2 C3 C4 121.44(11) . . ?
C2 C3 C4 117.15(11) . . ?
C5 C4 C3 119.29(11) . . ?
C5 C4 H4 120.4 . . ?
C3 C4 H4 120.4 . . ?
N1 C5 C4 122.97(12) . . ?
N1 C5 H5 118.5 . . ?
C4 C5 H5 118.5 . . ?
N3 C6 C7 122.78(12) . . ?
N3 C6 H6 118.6 . . ?
C7 C6 H6 118.6 . . ?
C6 C7 C8 119.30(11) . . ?
C6 C7 H7 120.3 . . ?
C8 C7 H7 120.3 . . ?
N4 C8 C7 121.90(11) . . ?
N4 C8 C9 120.92(12) . . ?
C7 C8 C9 117.17(11) . . ?
C10 C9 C8 119.73(11) . . ?
C10 C9 H9 120.1 . . ?
C8 C9 H9 120.1 . . ?
N3 C10 C9 122.40(11) . . ?
N3 C10 H10 118.8 . . ?
C9 C10 H10 118.8 . . ?
C5 N1 C1 118.20(11) . . ?
C5 N1 H1A 127(2) . . ?
C1 N1 H1A 115(2) . . ?
C3 N2 H2A 117.7(11) . . ?
C3 N2 H2B 118.7(12) . . ?
H2A N2 H2B 119.5(16) . . ?
C6 N3 C10 118.61(11) . . ?
C6 N3 H3A 117(2) . . ?
C10 N3 H3A 124(2) . . ?
C8 N4 H4A 119.1(12) . . ?
C8 N4 H4B 119.2(11) . . ?
H4A N4 H4B 121.2(16) . . ?

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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 C3 0.54(19) . . . . ?
C1 C2 C3 N2 -179.50(12) . . . . ?
C1 C2 C3 C4 -0.51(17) . . . . ?
N2 C3 C4 C5 178.97(12) . . . . ?
C2 C3 C4 C5 -0.01(17) . . . . ?
C3 C4 C5 N1 0.56(19) . . . . ?
N3 C6 C7 C8 0.68(19) . . . . ?
C6 C7 C8 N4 -178.85(12) . . . . ?
C6 C7 C8 C9 0.22(17) . . . . ?
N4 C8 C9 C10 178.24(12) . . . . ?
C7 C8 C9 C10 -0.84(17) . . . . ?
C8 C9 C10 N3 0.61(18) . . . . ?
C4 C5 N1 C1 -0.55(19) . . . . ?
C2 C1 N1 C5 -0.01(19) . . . . ?
C7 C6 N3 C10 -0.94(19) . . . . ?
C9 C10 N3 C6 0.27(18) . . . . ?

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
N1 H1A N3 0.89(4) 1.77(4) 2.6552(16) 173(3) 1_565
N2 H2A Cl1 0.858(17) 2.493(18) 3.3449(13) 172.1(15) .
N2 H2B Cl1 0.841(18) 2.640(18) 3.4464(13) 161.2(15) 2_556
N3 H3A N1 0.85(4) 1.81(4) 2.6552(16) 172(3) 1_545
N4 H4A Cl1 0.843(18) 2.543(18) 3.3472(14) 160.0(15) 4_665
N4 H4B Cl1 0.872(18) 2.428(18) 3.2980(13) 175.5(15) 2_656

_diffrn_measured_fraction_theta_max 0.940
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.438
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.055


data_[(4-AP)2H]Br
_database_code_depnum_ccdc_archive 'CCDC 857671'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            '4-aminopyridinium hemibromide'
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H13 N4, Br'
_chemical_formula_sum            'C10 H13 Br N4'
_chemical_formula_weight         269.15

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   9.7699(17)
_cell_length_b                   8.9930(15)
_cell_length_c                   13.460(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.826(3)
_cell_angle_gamma                90.00
_cell_volume                     1176.5(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3603
_cell_measurement_theta_min      2.46
_cell_measurement_theta_max      30.6

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.55
_exptl_crystal_size_min          0.09
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.520
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             544
_exptl_absorpt_coefficient_mu    3.468
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.2514
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2008)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker SMART Apex'
_diffrn_measurement_method       \w
_diffrn_detector_area_resol_mean 8.3
_diffrn_reflns_number            8850
_diffrn_reflns_av_R_equivalents  0.0396
_diffrn_reflns_av_sigmaI/netI    0.0510
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.46
_diffrn_reflns_theta_max         31.09
_reflns_number_total             3420
_reflns_number_gt                2857
_reflns_threshold_expression     >2/s(I)

_computing_data_collection       'Apex2 (Bruker, 2009)'
_computing_cell_refinement       'SAINT (Bruker, 2008)'
_computing_data_reduction        'SAINT (Bruker, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.

H atoms were located in a difference map and placed in calculated positions,
except for amine and pyridinium H atoms, whose positions were allowed to
refine.

The pyridinium H atoms were set to 50 % occupancy.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0369P)^2^+0.0999P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3420
_refine_ls_number_parameters     154
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0402
_refine_ls_R_factor_gt           0.0303
_refine_ls_wR_factor_ref         0.0828
_refine_ls_wR_factor_gt          0.0781
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.037
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.4701(2) 0.2333(2) 0.10345(14) 0.0212(4) Uani 1 1 d . . .
H1 H 0.4410 0.3334 0.0933 0.025 Uiso 1 1 calc R . .
C2 C 0.37866(19) 0.1315(2) 0.13385(14) 0.0200(4) Uani 1 1 d . . .
H2 H 0.2878 0.1612 0.1441 0.024 Uiso 1 1 calc R . .
C3 C 0.41995(19) -0.0167(2) 0.14976(13) 0.0174(3) Uani 1 1 d . . .
C4 C 0.5555(2) -0.0536(2) 0.13247(15) 0.0202(4) Uani 1 1 d . . .
H4 H 0.5878 -0.1527 0.1421 0.024 Uiso 1 1 calc R . .
C5 C 0.6404(2) 0.0546(2) 0.10169(16) 0.0222(4) Uani 1 1 d . . .
H5 H 0.7315 0.0282 0.0900 0.027 Uiso 1 1 calc R . .
C6 C 0.7942(2) 0.4709(2) -0.04168(15) 0.0204(4) Uani 1 1 d . . .
H6 H 0.7744 0.4080 -0.0980 0.024 Uiso 1 1 calc R . .
C7 C 0.86734(19) 0.5989(2) -0.05263(14) 0.0197(4) Uani 1 1 d . . .
H7 H 0.8972 0.6234 -0.1156 0.024 Uiso 1 1 calc R . .
C8 C 0.89794(18) 0.6937(2) 0.02933(14) 0.0180(3) Uani 1 1 d . . .
C9 C 0.84964(19) 0.6508(2) 0.12037(14) 0.0208(4) Uani 1 1 d . . .
H9 H 0.8671 0.7113 0.1781 0.025 Uiso 1 1 calc R . .
C10 C 0.7773(2) 0.5208(2) 0.12439(16) 0.0244(4) Uani 1 1 d . . .
H10 H 0.7452 0.4933 0.1861 0.029 Uiso 1 1 calc R . .
N1 N 0.59991(17) 0.19667(19) 0.08735(12) 0.0220(3) Uani 1 1 d . . .
H1A H 0.658(5) 0.265(6) 0.067(3) 0.026 Uiso 0.50 1 d P A 1
N2 N 0.33159(18) -0.1201(2) 0.17861(13) 0.0227(3) Uani 1 1 d . . .
H2A H 0.360(2) -0.202(3) 0.1930(17) 0.027 Uiso 1 1 d . . .
H2B H 0.258(3) -0.088(3) 0.1978(19) 0.027 Uiso 1 1 d . . .
N3 N 0.74948(18) 0.43065(19) 0.04583(14) 0.0225(3) Uani 1 1 d . . .
H3A H 0.713(5) 0.352(6) 0.062(4) 0.027 Uiso 0.50 1 d P B 2
N4 N 0.9715(2) 0.8181(2) 0.02127(14) 0.0264(4) Uani 1 1 d . . .
H4A H 0.991(3) 0.872(3) 0.069(2) 0.032 Uiso 1 1 d . . .
H4B H 0.997(2) 0.843(3) -0.0319(19) 0.032 Uiso 1 1 d . . .
Br1 Br 0.019628(18) 0.05704(2) 0.222706(13) 0.02067(8) 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 0.0242(9) 0.0156(9) 0.0235(9) -0.0015(7) 0.0004(7) -0.0012(7)
C2 0.0197(8) 0.0188(9) 0.0215(9) -0.0005(7) 0.0021(7) 0.0024(7)
C3 0.0204(8) 0.0162(8) 0.0149(8) -0.0010(7) -0.0022(7) -0.0002(7)
C4 0.0209(9) 0.0203(9) 0.0186(9) -0.0017(7) -0.0024(7) 0.0043(7)
C5 0.0171(9) 0.0255(10) 0.0235(10) -0.0015(7) -0.0008(7) 0.0011(7)
C6 0.0204(9) 0.0190(9) 0.0205(9) -0.0034(7) -0.0045(7) 0.0022(7)
C7 0.0236(9) 0.0180(9) 0.0167(9) 0.0008(7) -0.0017(7) 0.0030(7)
C8 0.0174(8) 0.0164(9) 0.0193(8) 0.0008(7) -0.0022(6) 0.0027(6)
C9 0.0232(9) 0.0217(9) 0.0173(9) -0.0026(7) -0.0001(7) -0.0001(7)
C10 0.0238(9) 0.0272(10) 0.0224(10) 0.0027(8) 0.0032(8) -0.0003(8)
N1 0.0206(7) 0.0204(8) 0.0248(8) -0.0012(6) 0.0010(6) -0.0046(6)
N2 0.0226(8) 0.0188(8) 0.0270(9) 0.0050(7) 0.0044(7) 0.0013(6)
N3 0.0192(8) 0.0198(9) 0.0280(9) 0.0012(7) 0.0001(7) -0.0031(6)
N4 0.0398(10) 0.0186(9) 0.0204(8) -0.0017(7) 0.0006(7) -0.0071(7)
Br1 0.02149(11) 0.02015(12) 0.02063(11) -0.00109(7) 0.00336(8) -0.00355(6)

_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.349(2) . ?
C1 C2 1.370(3) . ?
C1 H1 0.9500 . ?
C2 C3 1.403(3) . ?
C2 H2 0.9500 . ?
C3 N2 1.353(2) . ?
C3 C4 1.407(3) . ?
C4 C5 1.369(3) . ?
C4 H4 0.9500 . ?
C5 N1 1.346(2) . ?
C5 H5 0.9500 . ?
C6 N3 1.347(3) . ?
C6 C7 1.371(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.402(3) . ?
C7 H7 0.9500 . ?
C8 N4 1.340(2) . ?
C8 C9 1.411(3) . ?
C9 C10 1.370(3) . ?
C9 H9 0.9500 . ?
C10 N3 1.338(3) . ?
C10 H10 0.9500 . ?
N1 H1A 0.90(5) . ?
N2 H2A 0.80(2) . ?
N2 H2B 0.84(3) . ?
N3 H3A 0.83(6) . ?
N4 H4A 0.82(3) . ?
N4 H4B 0.81(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C2 122.50(18) . . ?
N1 C1 H1 118.7 . . ?
C2 C1 H1 118.7 . . ?
C1 C2 C3 119.60(17) . . ?
C1 C2 H2 120.2 . . ?
C3 C2 H2 120.2 . . ?
N2 C3 C2 121.01(17) . . ?
N2 C3 C4 121.62(18) . . ?
C2 C3 C4 117.36(17) . . ?
C5 C4 C3 119.45(17) . . ?
C5 C4 H4 120.3 . . ?
C3 C4 H4 120.3 . . ?
N1 C5 C4 122.66(18) . . ?
N1 C5 H5 118.7 . . ?
C4 C5 H5 118.7 . . ?
N3 C6 C7 122.59(18) . . ?
N3 C6 H6 118.7 . . ?
C7 C6 H6 118.7 . . ?
C6 C7 C8 119.87(18) . . ?
C6 C7 H7 120.1 . . ?
C8 C7 H7 120.1 . . ?
N4 C8 C7 121.15(18) . . ?
N4 C8 C9 121.88(18) . . ?
C7 C8 C9 116.96(17) . . ?
C10 C9 C8 119.15(17) . . ?
C10 C9 H9 120.4 . . ?
C8 C9 H9 120.4 . . ?
N3 C10 C9 123.36(18) . . ?
N3 C10 H10 118.3 . . ?
C9 C10 H10 118.3 . . ?
C5 N1 C1 118.42(17) . . ?
C5 N1 H1A 120(3) . . ?
C1 N1 H1A 121(3) . . ?
C3 N2 H2A 118.9(17) . . ?
C3 N2 H2B 116.2(16) . . ?
H2A N2 H2B 122(2) . . ?
C10 N3 C6 118.06(17) . . ?
C10 N3 H3A 112(3) . . ?
C6 N3 H3A 130(3) . . ?
C8 N4 H4A 121.3(18) . . ?
C8 N4 H4B 120.9(18) . . ?
H4A N4 H4B 118(2) . . ?

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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 C3 0.4(3) . . . . ?
C1 C2 C3 N2 -179.19(18) . . . . ?
C1 C2 C3 C4 -0.5(3) . . . . ?
N2 C3 C4 C5 178.89(19) . . . . ?
C2 C3 C4 C5 0.2(3) . . . . ?
C3 C4 C5 N1 0.3(3) . . . . ?
N3 C6 C7 C8 -0.1(3) . . . . ?
C6 C7 C8 N4 178.70(18) . . . . ?
C6 C7 C8 C9 -0.4(3) . . . . ?
N4 C8 C9 C10 -178.71(19) . . . . ?
C7 C8 C9 C10 0.3(3) . . . . ?
C8 C9 C10 N3 0.1(3) . . . . ?
C4 C5 N1 C1 -0.4(3) . . . . ?
C2 C1 N1 C5 0.1(3) . . . . ?
C9 C10 N3 C6 -0.5(3) . . . . ?
C7 C6 N3 C10 0.5(3) . . . . ?

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
N1 H1A N3 0.90(5) 1.77(6) 2.653(2) 165(4) .
N2 H2A Br1 0.80(2) 2.67(2) 3.4517(18) 167(2) 2_545
N2 H2B Br1 0.84(3) 2.72(3) 3.5422(19) 167(2) .
N3 H3A N1 0.83(6) 1.83(6) 2.653(2) 168(5) .
N4 H4A Br1 0.82(3) 2.64(3) 3.4540(19) 172(2) 1_665
N4 H4B Br1 0.81(3) 2.71(3) 3.4800(19) 158(2) 3_665

_diffrn_measured_fraction_theta_max 0.903
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.632
_refine_diff_density_min         -0.453
_refine_diff_density_rms         0.088

#===END