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The crystal structure of 2,4,6-collidine (2,4,6-tri­methyl­pyridine, C8H11N) has been determined at 180 (2) K following in situ crystal growth from the liquid. In space group P21/c, there are two mol­ecules in the asymmetric unit. Molecules are linked into one-dimensional chains via C—H...N interactions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536801018396/cf6121sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536801018396/cf6121Isup2.hkl
Contains datablock I

CCDC reference: 177193

Key indicators

  • Single-crystal X-ray study
  • T = 180 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.071
  • wR factor = 0.193
  • Data-to-parameter ratio = 15.8

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


Yellow Alert Alert Level C:
ABSTM_02 Alert C The ratio of expected to reported Tmax/Tmin(RR') is < 0.90 Tmin and Tmax reported: 0.796 0.955 Tmin' and Tmax expected: 1.000 1.000 RR' = 0.834 Please check that your absorption correction is appropriate.
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
1 Alert Level C = Please check

Computing details top

Data collection: COLLECT (Nonius, 1998); cell refinement: HKL and SCALEPACK (Otwinowski & Minor, 1997); data reduction: HKL, DENZO and SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick 1997); molecular graphics: XP (Sheldrick, 1993) and CAMERON (Watkin et al., 1996); software used to prepare material for publication: SHELXL97.

2,4,6-Trimethylpyridine top
Crystal data top
C8H11NDx = 1.049 Mg m3
Mr = 121.18Melting point: 230 K
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 8.7773 (5) ÅCell parameters from 16950 reflections
b = 20.3849 (11) Åθ = 1.0–25.0°
c = 8.9935 (4) ŵ = 0.06 mm1
β = 107.427 (3)°T = 180 K
V = 1535.29 (14) Å3Cylinder, colourless
Z = 80.15 mm (radius)
F(000) = 528
Data collection top
Nonius KappaCCD
diffractometer
2056 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.069
Thin slice ω and φ scansθmax = 25.1°, θmin = 3.8°
Absorption correction: multi-scan
(SORTAV; Blessing, 1995)
h = 1010
Tmin = 0.796, Tmax = 0.955k = 2424
11768 measured reflectionsl = 1010
2701 independent reflections
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)] = 0.071Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.193H-atom parameters constrained
S = 1.13 w = 1/[σ2(Fo2) + (0.0746P)2 + 0.8878P]
where P = (Fo2 + 2Fc2)/3
2701 reflections(Δ/σ)max = 0.024
171 parametersΔρmax = 0.21 e Å3
0 restraintsΔρmin = 0.19 e Å3
Special details top

Experimental. Grown in situ in a 0.3 mm Lindemann capillary at 212 K

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.

Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)

Pyridine ring 1

-0.1873 (0.0074)x + 20.3784 (0.0013)y + 0.1741 (0.0082)z = 18.5838 (0.0098)

* 0.0012 (0.0014) N1A * 0.0024 (0.0015) C2A * -0.0049 (0.0015) C3A * 0.0040 (0.0015) C4A * -0.0006 (0.0016) C5A * -0.0021 (0.0015) C6A

Rms deviation of fitted atoms = 0.0030

Pyridine ring 2

5.8307 (0.0061)x + 8.1727 (0.0178)y - 7.2024 (0.0048)z = 9.1850 (0.0147)

* -0.0034 (0.0015) N1B * -0.0059 (0.0016) C2B * 0.0102 (0.0017) C3B * -0.0056 (0.0016) C4B * -0.0033 (0.0015) C5B * 0.0079 (0.0015) C6B

Rms deviation of fitted atoms = 0.0065

Angle to previous plane (with approximate e.s.d.) = 67.79 (0.07)

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*/UeqOcc. (<1)
N1A1.3594 (2)0.91500 (9)1.1117 (2)0.0369 (5)
C2A1.2878 (3)0.91572 (11)0.9567 (3)0.0372 (6)
C3A1.1226 (3)0.91440 (11)0.8918 (3)0.0386 (6)
H3A1.07650.91440.78180.051 (4)*
C4A1.0248 (3)0.91311 (10)0.9885 (3)0.0392 (6)
C5A1.1001 (3)0.91222 (11)1.1481 (3)0.0397 (6)
H5A1.03810.91091.21840.051 (4)*
C6A1.2649 (3)0.91317 (11)1.2051 (3)0.0375 (6)
C7A1.3977 (3)0.91774 (14)0.8560 (3)0.0517 (7)
H7AA1.47620.88230.88660.098 (3)*
H7BA1.45310.96010.86940.098 (3)*
H7CA1.33500.91220.74650.098 (3)*
C8A0.8456 (3)0.91212 (13)0.9243 (3)0.0510 (7)
H8AA0.80130.95010.96390.098 (3)*
H8BA0.80440.87170.95700.098 (3)*
H8CA0.81440.91400.81030.098 (3)*
C9A1.3493 (3)0.91192 (14)1.3778 (3)0.0519 (7)
H9AA1.42080.87391.40290.098 (3)*
H9BA1.27020.90881.43470.098 (3)*
H9CA1.41170.95221.40810.098 (3)*
N1B0.9841 (2)0.85586 (9)0.4930 (2)0.0411 (5)
C2B1.0232 (3)0.79541 (11)0.4565 (3)0.0416 (6)
C3B0.9255 (3)0.75946 (12)0.3343 (3)0.0445 (6)
H3B0.95900.71740.31070.051 (4)*
C4B0.7790 (3)0.78423 (12)0.2460 (3)0.0419 (6)
C5B0.7392 (3)0.84653 (12)0.2841 (3)0.0399 (6)
H5B0.64040.86570.22680.051 (4)*
C6B0.8433 (3)0.88085 (12)0.4059 (3)0.0392 (6)
C7B1.1806 (3)0.76838 (14)0.5575 (4)0.0578 (8)
H7AB1.25130.80470.60550.098 (3)*
H7BB1.23060.74230.49320.098 (3)*
H7CB1.16190.74050.63910.098 (3)*
C8B0.6669 (4)0.74532 (16)0.1172 (3)0.0609 (8)
H8AB0.58690.77470.05040.098 (3)*0.49 (4)
H8BB0.61330.71200.16210.098 (3)*0.49 (4)
H8CB0.72730.72390.05520.098 (3)*0.49 (4)
H8DB0.69800.69900.12810.098 (3)*0.51 (4)
H8EB0.67170.76180.01640.098 (3)*0.51 (4)
H8FB0.55770.74980.12330.098 (3)*0.51 (4)
C9B0.8038 (3)0.94906 (13)0.4465 (4)0.0578 (8)
H9AB0.82140.95210.55920.098 (3)*
H9BB0.69170.95880.39140.098 (3)*
H9CB0.87260.98070.41550.098 (3)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N1A0.0324 (11)0.0377 (11)0.0391 (11)0.0020 (8)0.0084 (8)0.0019 (8)
C2A0.0332 (12)0.0376 (13)0.0395 (13)0.0005 (10)0.0088 (10)0.0040 (9)
C3A0.0349 (13)0.0386 (13)0.0389 (13)0.0009 (10)0.0059 (10)0.0048 (10)
C4A0.0325 (13)0.0306 (12)0.0522 (14)0.0004 (9)0.0091 (11)0.0029 (10)
C5A0.0372 (13)0.0376 (13)0.0470 (14)0.0013 (10)0.0165 (11)0.0010 (10)
C6A0.0373 (13)0.0340 (12)0.0411 (13)0.0010 (9)0.0116 (10)0.0011 (9)
C7A0.0413 (15)0.0690 (18)0.0474 (15)0.0037 (13)0.0174 (12)0.0062 (13)
C8A0.0293 (13)0.0515 (16)0.0681 (18)0.0022 (11)0.0084 (12)0.0052 (12)
C9A0.0490 (16)0.0683 (18)0.0378 (14)0.0018 (13)0.0123 (12)0.0027 (12)
N1B0.0346 (11)0.0420 (11)0.0449 (11)0.0024 (9)0.0091 (9)0.0061 (9)
C2B0.0324 (13)0.0397 (13)0.0512 (14)0.0013 (10)0.0103 (11)0.0071 (11)
C3B0.0377 (14)0.0423 (14)0.0536 (15)0.0012 (11)0.0140 (12)0.0014 (11)
C4B0.0354 (13)0.0512 (15)0.0403 (13)0.0016 (11)0.0133 (11)0.0007 (10)
C5B0.0308 (12)0.0525 (15)0.0364 (12)0.0050 (10)0.0101 (10)0.0082 (10)
C6B0.0332 (13)0.0427 (13)0.0428 (13)0.0043 (10)0.0131 (10)0.0079 (10)
C7B0.0397 (16)0.0497 (16)0.0745 (19)0.0076 (12)0.0028 (14)0.0085 (13)
C8B0.0492 (17)0.074 (2)0.0540 (16)0.0015 (14)0.0078 (13)0.0152 (14)
C9B0.0476 (17)0.0473 (16)0.074 (2)0.0065 (13)0.0116 (14)0.0012 (13)
Geometric parameters (Å, º) top
N1A—C6A1.345 (3)C2B—C3B1.384 (3)
N1A—C2A1.347 (3)C2B—C7B1.512 (3)
C2A—C3A1.392 (3)C3B—C4B1.388 (3)
C2A—C7A1.508 (3)C3B—H3B0.950
C3A—C4A1.393 (3)C4B—C5B1.387 (3)
C3A—H3A0.950C4B—C8B1.502 (4)
C4A—C5A1.389 (3)C5B—C6B1.387 (3)
C4A—C8A1.505 (3)C5B—H5B0.950
C5A—C6A1.383 (3)C6B—C9B1.504 (4)
C5A—H5A0.950C7B—H7AB0.980
C6A—C9A1.508 (3)C7B—H7BB0.980
C7A—H7AA0.980C7B—H7CB0.980
C7A—H7BA0.980C8B—H8AB0.980
C7A—H7CA0.980C8B—H8BB0.980
C8A—H8AA0.980C8B—H8CB0.980
C8A—H8BA0.980C8B—H8DB0.980
C8A—H8CA0.980C8B—H8EB0.980
C9A—H9AA0.980C8B—H8FB0.980
C9A—H9BA0.980C9B—H9AB0.980
C9A—H9CA0.980C9B—H9BB0.980
N1B—C2B1.346 (3)C9B—H9CB0.980
N1B—C6B1.349 (3)
C6A—N1A—C2A117.6 (2)C5B—C4B—C8B121.2 (2)
N1A—C2A—C3A122.5 (2)C3B—C4B—C8B122.0 (2)
N1A—C2A—C7A116.0 (2)C4B—C5B—C6B120.1 (2)
C3A—C2A—C7A121.5 (2)C4B—C5B—H5B120.0
C2A—C3A—C4A119.9 (2)C6B—C5B—H5B120.0
C2A—C3A—H3A120.1N1B—C6B—C5B122.7 (2)
C4A—C3A—H3A120.1N1B—C6B—C9B116.5 (2)
C5A—C4A—C3A117.0 (2)C5B—C6B—C9B120.8 (2)
C5A—C4A—C8A121.0 (2)C2B—C7B—H7AB109.5
C3A—C4A—C8A121.9 (2)C2B—C7B—H7BB109.5
C6A—C5A—C4A120.2 (2)H7AB—C7B—H7BB109.5
C6A—C5A—H5A119.9C2B—C7B—H7CB109.5
C4A—C5A—H5A119.9H7AB—C7B—H7CB109.5
N1A—C6A—C5A122.8 (2)H7BB—C7B—H7CB109.5
N1A—C6A—C9A116.1 (2)C4B—C8B—H8AB109.5
C5A—C6A—C9A121.2 (2)C4B—C8B—H8BB109.5
C2A—C7A—H7AA109.5H8AB—C8B—H8BB109.5
C2A—C7A—H7BA109.5C4B—C8B—H8CB109.5
H7AA—C7A—H7BA109.5H8AB—C8B—H8CB109.5
C2A—C7A—H7CA109.5H8BB—C8B—H8CB109.5
H7AA—C7A—H7CA109.5C4B—C8B—H8DB109.5
H7BA—C7A—H7CA109.5H8AB—C8B—H8DB141.1
C4A—C8A—H8AA109.5H8BB—C8B—H8DB56.3
C4A—C8A—H8BA109.5H8CB—C8B—H8DB56.3
H8AA—C8A—H8BA109.5C4B—C8B—H8EB109.5
C4A—C8A—H8CA109.5H8AB—C8B—H8EB56.3
H8AA—C8A—H8CA109.5H8BB—C8B—H8EB141.1
H8BA—C8A—H8CA109.5H8CB—C8B—H8EB56.3
C6A—C9A—H9AA109.5H8DB—C8B—H8EB109.5
C6A—C9A—H9BA109.5C4B—C8B—H8FB109.5
H9AA—C9A—H9BA109.5H8AB—C8B—H8FB56.3
C6A—C9A—H9CA109.5H8BB—C8B—H8FB56.3
H9AA—C9A—H9CA109.5H8CB—C8B—H8FB141.1
H9BA—C9A—H9CA109.5H8DB—C8B—H8FB109.5
C2B—N1B—C6B117.4 (2)H8EB—C8B—H8FB109.5
N1B—C2B—C3B122.4 (2)C6B—C9B—H9AB109.5
N1B—C2B—C7B116.2 (2)C6B—C9B—H9BB109.5
C3B—C2B—C7B121.4 (2)H9AB—C9B—H9BB109.5
C2B—C3B—C4B120.6 (2)C6B—C9B—H9CB109.5
C2B—C3B—H3B119.7H9AB—C9B—H9CB109.5
C4B—C3B—H3B119.7H9BB—C9B—H9CB109.5
C5B—C4B—C3B116.8 (2)
C6A—N1A—C2A—C3A0.3 (3)C6B—N1B—C2B—C3B0.4 (3)
C6A—N1A—C2A—C7A180.0 (2)C6B—N1B—C2B—C7B179.2 (2)
N1A—C2A—C3A—C4A0.8 (3)N1B—C2B—C3B—C4B1.7 (4)
C7A—C2A—C3A—C4A179.5 (2)C7B—C2B—C3B—C4B177.9 (2)
C2A—C3A—C4A—C5A1.0 (3)C2B—C3B—C4B—C5B1.6 (4)
C2A—C3A—C4A—C8A179.6 (2)C2B—C3B—C4B—C8B177.3 (2)
C3A—C4A—C5A—C6A0.5 (3)C3B—C4B—C5B—C6B0.3 (3)
C8A—C4A—C5A—C6A180.0 (2)C8B—C4B—C5B—C6B178.6 (2)
C2A—N1A—C6A—C5A0.2 (3)C2B—N1B—C6B—C5B1.0 (3)
C2A—N1A—C6A—C9A179.6 (2)C2B—N1B—C6B—C9B178.7 (2)
C4A—C5A—C6A—N1A0.0 (3)C4B—C5B—C6B—N1B1.0 (3)
C4A—C5A—C6A—C9A179.7 (2)C4B—C5B—C6B—C9B178.6 (2)
 

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