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The crystal structure of the title compound, C6H9N2+·Cl-, is stabilized by extensive hydrogen bonding.
Supporting information
CCDC reference: 274658
Key indicators
- Single-crystal X-ray study
- T = 100 K
- Mean (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
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+·Cl− | F(000) = 304 |
Mr = 144.60 | Dx = 1.319 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 4476 reflections |
a = 7.8401 (9) Å | θ = 2.7–28.2° |
b = 12.5177 (14) Å | µ = 0.44 mm−1 |
c = 7.6177 (8) Å | T = 100 K |
β = 103.049 (2)° | Plate, colourless |
V = 728.30 (14) Å3 | 0.20 × 0.17 × 0.05 mm |
Z = 4 | |
Data collection top
Bruker APEX CCD area-detector diffractometer | 1687 independent reflections |
Radiation source: fine-focus sealed tube | 1523 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.022 |
ω scans | θmax = 28.2°, θmin = 2.7° |
Absorption correction: multi-scan (Blessing, 1995) | h = −9→9 |
Tmin = 0.899, Tmax = 0.979 | k = −16→16 |
4476 measured reflections | l = −9→5 |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.036 | Hydrogen site location: geom and difmap |
wR(F2) = 0.090 | H-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 parameters | Δρmax = 0.42 e Å−3 |
0 restraints | Δρmin = −0.18 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
N1 | 1.17584 (16) | 0.11932 (10) | 0.30150 (18) | 0.0213 (3) | |
C2 | 1.07022 (19) | 0.03765 (13) | 0.2354 (2) | 0.0210 (3) | |
H2 | 1.1128 | −0.0158 | 0.1678 | 0.025* | |
C3 | 0.90136 (18) | 0.02778 (12) | 0.2614 (2) | 0.0192 (3) | |
H3 | 0.8299 | −0.0308 | 0.2110 | 0.023* | |
C4 | 0.83835 (18) | 0.10423 (11) | 0.36171 (19) | 0.0165 (3) | |
C5 | 0.94708 (19) | 0.18963 (12) | 0.4300 (2) | 0.0209 (3) | |
H5 | 0.9081 | 0.2439 | 0.4988 | 0.025* | |
C6 | 1.11275 (19) | 0.19389 (13) | 0.3959 (2) | 0.0232 (3) | |
H6 | 1.1857 | 0.2528 | 0.4417 | 0.028* | |
C7 | 0.65737 (18) | 0.09302 (12) | 0.3985 (2) | 0.0182 (3) | |
H7A | 0.6297 | 0.0164 | 0.4084 | 0.022* | |
H7B | 0.6546 | 0.1280 | 0.5144 | 0.022* | |
N8 | 0.52382 (15) | 0.14282 (10) | 0.25099 (16) | 0.0164 (3) | |
H8A | 0.5373 | 0.2150 | 0.2551 | 0.025* | |
H8B | 0.4148 | 0.1258 | 0.2649 | 0.025* | |
H8C | 0.5377 | 0.1180 | 0.1428 | 0.025* | |
Cl9 | 0.55948 (5) | 0.38254 (3) | 0.34913 (5) | 0.02158 (14) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
N1 | 0.0134 (6) | 0.0286 (7) | 0.0222 (7) | 0.0017 (5) | 0.0044 (5) | 0.0040 (5) |
C2 | 0.0179 (7) | 0.0272 (8) | 0.0182 (7) | 0.0048 (6) | 0.0044 (6) | −0.0009 (6) |
C3 | 0.0166 (7) | 0.0216 (7) | 0.0191 (8) | −0.0004 (6) | 0.0036 (6) | −0.0018 (6) |
C4 | 0.0134 (6) | 0.0229 (7) | 0.0132 (7) | 0.0015 (5) | 0.0031 (5) | 0.0038 (5) |
C5 | 0.0174 (7) | 0.0219 (7) | 0.0233 (8) | 0.0010 (6) | 0.0043 (6) | −0.0024 (6) |
C6 | 0.0166 (7) | 0.0231 (8) | 0.0291 (9) | −0.0029 (6) | 0.0037 (6) | −0.0006 (6) |
C7 | 0.0142 (7) | 0.0244 (7) | 0.0166 (7) | −0.0003 (5) | 0.0047 (5) | 0.0020 (6) |
N8 | 0.0117 (5) | 0.0199 (6) | 0.0182 (6) | −0.0005 (5) | 0.0046 (5) | −0.0012 (5) |
Cl9 | 0.0291 (2) | 0.0186 (2) | 0.0191 (2) | 0.00100 (14) | 0.00992 (15) | 0.00041 (13) |
Geometric parameters (Å, º) top
N1—C6 | 1.339 (2) | C5—H5 | 0.9500 |
N1—C2 | 1.340 (2) | C6—H6 | 0.9500 |
C2—C3 | 1.388 (2) | C7—N8 | 1.4887 (18) |
C2—H2 | 0.9500 | C7—H7A | 0.9900 |
C3—C4 | 1.383 (2) | C7—H7B | 0.9900 |
C3—H3 | 0.9500 | N8—H8A | 0.9100 |
C4—C5 | 1.393 (2) | N8—H8B | 0.9100 |
C4—C7 | 1.5136 (19) | N8—H8C | 0.9100 |
C5—C6 | 1.382 (2) | | |
| | | |
C6—N1—C2 | 117.50 (13) | N1—C6—H6 | 118.3 |
N1—C2—C3 | 122.86 (14) | C5—C6—H6 | 118.3 |
N1—C2—H2 | 118.6 | N8—C7—C4 | 110.51 (12) |
C3—C2—H2 | 118.6 | N8—C7—H7A | 109.5 |
C4—C3—C2 | 119.24 (14) | C4—C7—H7A | 109.5 |
C4—C3—H3 | 120.4 | N8—C7—H7B | 109.5 |
C2—C3—H3 | 120.4 | C4—C7—H7B | 109.5 |
C3—C4—C5 | 118.20 (13) | H7A—C7—H7B | 108.1 |
C3—C4—C7 | 120.31 (13) | C7—N8—H8A | 109.5 |
C5—C4—C7 | 121.48 (13) | C7—N8—H8B | 109.5 |
C6—C5—C4 | 118.76 (14) | H8A—N8—H8B | 109.5 |
C6—C5—H5 | 120.6 | C7—N8—H8C | 109.5 |
C4—C5—H5 | 120.6 | H8A—N8—H8C | 109.5 |
N1—C6—C5 | 123.43 (14) | H8B—N8—H8C | 109.5 |
| | | |
C6—N1—C2—C3 | −0.2 (2) | C7—C4—C5—C6 | 178.25 (14) |
N1—C2—C3—C4 | −0.9 (2) | C2—N1—C6—C5 | 1.0 (2) |
C2—C3—C4—C5 | 1.2 (2) | C4—C5—C6—N1 | −0.7 (2) |
C2—C3—C4—C7 | −177.53 (13) | C3—C4—C7—N8 | −88.16 (16) |
C3—C4—C5—C6 | −0.4 (2) | C5—C4—C7—N8 | 93.19 (16) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N8—H8A···Cl9 | 0.91 | 2.21 | 3.0899 (14) | 163 |
N8—H8B···N1i | 0.91 | 1.96 | 2.8551 (18) | 169 |
N8—H8C···Cl9ii | 0.91 | 2.28 | 3.1523 (13) | 160 |
Symmetry codes: (i) x−1, y, z; (ii) x, −y+1/2, z−1/2. |
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