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In the title compound, C12H12N3O2+·Br, the bromide anion and most atoms of the cation lie on a mirror plane. In the cation, the pyridine and benzene rings are almost orthogonal to each other, forming a dihedral angle of 89.2 (1)°. The crystal packing is stabilized by weak N—H...Br and C—H...O inter­molecular hydrogen bonds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806005605/cv6638sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806005605/cv6638Isup2.hkl
Contains datablock I

CCDC reference: 601789

Key indicators

  • Single-crystal X-ray study
  • T = 273 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.024
  • wR factor = 0.068
  • Data-to-parameter ratio = 10.9

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT164_ALERT_4_C Nr. of Refined C-H H-Atoms in Heavy-At Struct... 1
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: DIRDIF99 (Beurskens et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997), PLATON (Spek, 2003) and Qmol (Gans & Shalloway, 2001); software used to prepare material for publication: SHELXL97 and PARST (Nardelli, 1995).

4-Amino-1-(4-nitrobenzyl)pyridinium bromide top
Crystal data top
C12H12N3O2+·BrDx = 1.636 Mg m3
Mr = 310.16Melting point = 561–563 K
Orthorhombic, CmcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2bc 2Cell parameters from 6556 reflections
a = 6.7257 (4) Åθ = 5.4–53.1°
b = 14.3806 (8) ŵ = 3.26 mm1
c = 26.0364 (15) ÅT = 273 K
V = 2518.2 (3) Å3Prism, colourless
Z = 80.10 × 0.10 × 0.07 mm
F(000) = 1248
Data collection top
Bruker SMART CCD area-detector
diffractometer
1134 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.032
Graphite monochromatorθmax = 25.0°, θmin = 2.8°
ω scansh = 77
11396 measured reflectionsk = 1616
1205 independent reflectionsl = 3030
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.024Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.068H atoms treated by a mixture of independent and constrained refinement
S = 1.06 w = 1/[σ2(Fo2) + (0.033P)2 + 2.5916P]
where P = (Fo2 + 2Fc2)/3
1205 reflections(Δ/σ)max = 0.001
111 parametersΔρmax = 0.20 e Å3
2 restraintsΔρmin = 0.38 e Å3
Special details top

Geometry. 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.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Br0.00000.63077 (2)0.397489 (12)0.05028 (15)
O10.00000.20910 (16)0.31724 (9)0.0799 (9)
O20.00000.33546 (18)0.35970 (7)0.0620 (6)
N10.00000.45006 (15)0.08501 (8)0.0356 (5)
N20.00000.3128 (2)0.05308 (10)0.0560 (7)
H2N0.117 (3)0.3041 (18)0.0675 (9)0.069 (8)*
N30.00000.29295 (18)0.31927 (9)0.0448 (6)
C10.1729 (3)0.42638 (14)0.06279 (7)0.0426 (4)
H10.29180.44240.07870.051*
C20.1777 (3)0.37939 (13)0.01747 (8)0.0446 (5)
H20.29900.36300.00290.053*
C30.00000.35571 (18)0.00732 (10)0.0403 (6)
C60.00000.50430 (19)0.13327 (10)0.0415 (6)
H60.115 (3)0.5424 (13)0.1325 (7)0.042 (5)*
C70.00000.44449 (18)0.18069 (9)0.0329 (5)
C80.00000.49016 (19)0.22810 (9)0.0387 (6)
H80.00000.55480.22890.046*
C90.00000.44144 (19)0.27341 (10)0.0381 (6)
H90.00000.47220.30480.046*
C100.00000.34555 (19)0.27113 (9)0.0350 (6)
C110.00000.29802 (19)0.22501 (10)0.0379 (6)
H110.00000.23340.22440.045*
C120.00000.34850 (19)0.17977 (10)0.0353 (6)
H120.00000.31750.14840.042*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br0.0510 (2)0.0486 (2)0.0513 (2)0.0000.0000.01078 (12)
O10.146 (3)0.0410 (14)0.0524 (13)0.0000.0000.0156 (10)
O20.0914 (18)0.0677 (15)0.0268 (10)0.0000.0000.0049 (10)
N10.0461 (13)0.0361 (12)0.0246 (10)0.0000.0000.0039 (8)
N20.084 (2)0.0501 (15)0.0341 (13)0.0000.0000.0068 (11)
N30.0491 (14)0.0510 (15)0.0344 (12)0.0000.0000.0102 (10)
C10.0403 (11)0.0507 (11)0.0367 (9)0.0015 (9)0.0031 (8)0.0031 (8)
C20.0442 (12)0.0517 (12)0.0379 (10)0.0063 (8)0.0064 (9)0.0003 (8)
C30.0628 (18)0.0303 (13)0.0276 (13)0.0000.0000.0048 (10)
C60.0631 (19)0.0338 (14)0.0276 (12)0.0000.0000.0003 (10)
C70.0348 (13)0.0363 (14)0.0276 (12)0.0000.0000.0022 (10)
C80.0511 (16)0.0320 (13)0.0331 (12)0.0000.0000.0020 (10)
C90.0465 (15)0.0409 (15)0.0270 (12)0.0000.0000.0043 (10)
C100.0368 (14)0.0395 (14)0.0287 (12)0.0000.0000.0061 (10)
C110.0440 (15)0.0320 (13)0.0377 (13)0.0000.0000.0024 (11)
C120.0412 (14)0.0368 (13)0.0278 (12)0.0000.0000.0031 (10)
Geometric parameters (Å, º) top
O1—N31.207 (3)C6—C71.505 (3)
O2—N31.217 (3)C6—H60.948 (15)
N1—C11.343 (2)C7—C121.381 (4)
N1—C1i1.343 (2)C7—C81.398 (3)
N1—C61.479 (3)C8—C91.372 (3)
N2—C31.342 (4)C8—H80.9300
N2—H2N0.881 (16)C9—C101.380 (4)
N3—C101.464 (3)C9—H90.9300
C1—C21.360 (3)C10—C111.382 (4)
C1—H10.9300C11—C121.384 (4)
C2—C31.400 (3)C11—H110.9300
C2—H20.9300C12—H120.9300
C3—C2i1.400 (3)
C1—N1—C1i120.0 (2)C12—C7—C8119.0 (2)
C1—N1—C6119.98 (11)C12—C7—C6123.9 (2)
C1i—N1—C6119.98 (11)C8—C7—C6117.1 (2)
C3—N2—H2N116.3 (18)C9—C8—C7121.3 (2)
O1—N3—O2122.7 (2)C9—C8—H8119.4
O1—N3—C10118.6 (2)C7—C8—H8119.4
O2—N3—C10118.7 (2)C8—C9—C10118.2 (2)
N1—C1—C2121.33 (19)C8—C9—H9120.9
N1—C1—H1119.3C10—C9—H9120.9
C2—C1—H1119.3C9—C10—C11122.1 (2)
C1—C2—C3120.1 (2)C9—C10—N3118.6 (2)
C1—C2—H2120.0C11—C10—N3119.2 (2)
C3—C2—H2120.0C10—C11—C12118.7 (2)
N2—C3—C2121.42 (12)C10—C11—H11120.7
N2—C3—C2i121.42 (12)C12—C11—H11120.7
C2—C3—C2i117.2 (2)C7—C12—C11120.7 (2)
N1—C6—C7113.3 (2)C7—C12—H12119.7
N1—C6—H6106.7 (12)C11—C12—H12119.7
C7—C6—H6110.3 (12)
C1i—N1—C1—C20.8 (4)C8—C9—C10—C110.0
C6—N1—C1—C2177.6 (2)C8—C9—C10—N3180.0
N1—C1—C2—C30.8 (3)O1—N3—C10—C9180.0
C1—C2—C3—N2177.2 (2)O2—N3—C10—C90.0
C1—C2—C3—C2i2.3 (4)O1—N3—C10—C110.0
C1—N1—C6—C790.78 (19)O2—N3—C10—C11180.0
C1i—N1—C6—C790.78 (19)C9—C10—C11—C120.0
N1—C6—C7—C120.0N3—C10—C11—C12180.0
N1—C6—C7—C8180.0C8—C7—C12—C110.0
C12—C7—C8—C90.0C6—C7—C12—C11180.0
C6—C7—C8—C9180.0C10—C11—C12—C70.0
C7—C8—C9—C100.0
Symmetry code: (i) x, y, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2N···Brii0.88 (2)2.89 (2)3.6912 (11)152 (2)
C8—H8···O1iii0.932.523.363 (4)150
Symmetry codes: (ii) x1/2, y+1, z1/2; (iii) x, y+1/2, z+1/2.
 

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