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The crystal structure of the title compound, C6H9N2+·Cl-, is stabilized by extensive hydrogen bonding.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805013255/wk6048sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805013255/wk6048Isup2.hkl
Contains datablock I

CCDC reference: 274658

Key indicators

  • Single-crystal X-ray study
  • T = 100 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.036
  • wR factor = 0.090
  • Data-to-parameter ratio = 20.3

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.37
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 1 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 0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: X-SEED.

(4-Pyridylmethyl)aminium chloride top
Crystal data top
C6H9N2+·ClF(000) = 304
Mr = 144.60Dx = 1.319 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 4476 reflections
a = 7.8401 (9) Åθ = 2.7–28.2°
b = 12.5177 (14) ŵ = 0.44 mm1
c = 7.6177 (8) ÅT = 100 K
β = 103.049 (2)°Plate, colourless
V = 728.30 (14) Å30.20 × 0.17 × 0.05 mm
Z = 4
Data collection top
Bruker APEX CCD area-detector
diffractometer
1687 independent reflections
Radiation source: fine-focus sealed tube1523 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.022
ω scansθmax = 28.2°, θmin = 2.7°
Absorption correction: multi-scan
(Blessing, 1995)
h = 99
Tmin = 0.899, Tmax = 0.979k = 1616
4476 measured reflectionsl = 95
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)] = 0.036Hydrogen site location: geom and difmap
wR(F2) = 0.090H-atom parameters constrained
S = 1.08 w = 1/[σ2(Fo2) + (0.0452P)2 + 0.2493P]
where P = (Fo2 + 2Fc2)/3
1687 reflections(Δ/σ)max < 0.001
83 parametersΔρmax = 0.42 e Å3
0 restraintsΔρmin = 0.18 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
N11.17584 (16)0.11932 (10)0.30150 (18)0.0213 (3)
C21.07022 (19)0.03765 (13)0.2354 (2)0.0210 (3)
H21.11280.01580.16780.025*
C30.90136 (18)0.02778 (12)0.2614 (2)0.0192 (3)
H30.82990.03080.21100.023*
C40.83835 (18)0.10423 (11)0.36171 (19)0.0165 (3)
C50.94708 (19)0.18963 (12)0.4300 (2)0.0209 (3)
H50.90810.24390.49880.025*
C61.11275 (19)0.19389 (13)0.3959 (2)0.0232 (3)
H61.18570.25280.44170.028*
C70.65737 (18)0.09302 (12)0.3985 (2)0.0182 (3)
H7A0.62970.01640.40840.022*
H7B0.65460.12800.51440.022*
N80.52382 (15)0.14282 (10)0.25099 (16)0.0164 (3)
H8A0.53730.21500.25510.025*
H8B0.41480.12580.26490.025*
H8C0.53770.11800.14280.025*
Cl90.55948 (5)0.38254 (3)0.34913 (5)0.02158 (14)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0134 (6)0.0286 (7)0.0222 (7)0.0017 (5)0.0044 (5)0.0040 (5)
C20.0179 (7)0.0272 (8)0.0182 (7)0.0048 (6)0.0044 (6)0.0009 (6)
C30.0166 (7)0.0216 (7)0.0191 (8)0.0004 (6)0.0036 (6)0.0018 (6)
C40.0134 (6)0.0229 (7)0.0132 (7)0.0015 (5)0.0031 (5)0.0038 (5)
C50.0174 (7)0.0219 (7)0.0233 (8)0.0010 (6)0.0043 (6)0.0024 (6)
C60.0166 (7)0.0231 (8)0.0291 (9)0.0029 (6)0.0037 (6)0.0006 (6)
C70.0142 (7)0.0244 (7)0.0166 (7)0.0003 (5)0.0047 (5)0.0020 (6)
N80.0117 (5)0.0199 (6)0.0182 (6)0.0005 (5)0.0046 (5)0.0012 (5)
Cl90.0291 (2)0.0186 (2)0.0191 (2)0.00100 (14)0.00992 (15)0.00041 (13)
Geometric parameters (Å, º) top
N1—C61.339 (2)C5—H50.9500
N1—C21.340 (2)C6—H60.9500
C2—C31.388 (2)C7—N81.4887 (18)
C2—H20.9500C7—H7A0.9900
C3—C41.383 (2)C7—H7B0.9900
C3—H30.9500N8—H8A0.9100
C4—C51.393 (2)N8—H8B0.9100
C4—C71.5136 (19)N8—H8C0.9100
C5—C61.382 (2)
C6—N1—C2117.50 (13)N1—C6—H6118.3
N1—C2—C3122.86 (14)C5—C6—H6118.3
N1—C2—H2118.6N8—C7—C4110.51 (12)
C3—C2—H2118.6N8—C7—H7A109.5
C4—C3—C2119.24 (14)C4—C7—H7A109.5
C4—C3—H3120.4N8—C7—H7B109.5
C2—C3—H3120.4C4—C7—H7B109.5
C3—C4—C5118.20 (13)H7A—C7—H7B108.1
C3—C4—C7120.31 (13)C7—N8—H8A109.5
C5—C4—C7121.48 (13)C7—N8—H8B109.5
C6—C5—C4118.76 (14)H8A—N8—H8B109.5
C6—C5—H5120.6C7—N8—H8C109.5
C4—C5—H5120.6H8A—N8—H8C109.5
N1—C6—C5123.43 (14)H8B—N8—H8C109.5
C6—N1—C2—C30.2 (2)C7—C4—C5—C6178.25 (14)
N1—C2—C3—C40.9 (2)C2—N1—C6—C51.0 (2)
C2—C3—C4—C51.2 (2)C4—C5—C6—N10.7 (2)
C2—C3—C4—C7177.53 (13)C3—C4—C7—N888.16 (16)
C3—C4—C5—C60.4 (2)C5—C4—C7—N893.19 (16)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N8—H8A···Cl90.912.213.0899 (14)163
N8—H8B···N1i0.911.962.8551 (18)169
N8—H8C···Cl9ii0.912.283.1523 (13)160
Symmetry codes: (i) x1, y, z; (ii) x, y+1/2, z1/2.
 

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