Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536801017548/bt6088sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536801017548/bt6088Isup2.hkl |
CCDC reference: 176028
Key indicators
- Single-crystal X-ray study
- T = 120 K
- Mean (C-C) = 0.003 Å
- Disorder in main residue
- R factor = 0.062
- wR factor = 0.181
- Data-to-parameter ratio = 10.5
checkCIF results
No syntax errors found ADDSYM reports no extra symmetry
Alert Level C:
RINTA_01 Alert C The value of Rint is greater than 0.10 Rint given 0.109 PLAT_302 Alert C Anion/Solvent Disorder ....................... 12.00 Perc. General Notes
REFLT_03 From the CIF: _diffrn_reflns_theta_max 27.46 From the CIF: _reflns_number_total 749 Count of symmetry unique reflns 762 Completeness (_total/calc) 98.29% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 0 Fraction of Friedel pairs measured 0.000 Are heavy atom types Z>Si present no Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF.
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
2 Alert Level C = Please check
The sample (99%) was obtained from the Aldrich Company and was used without further purification. The crystal was grown in a 0.3 mm glass capillary tube at 206 K (a temperature only slightly less than the melting point of the solid in the capillary tube) using a technique described previously (Davies & Bond, 2001). The crystal was subsequently cooled to 120 (2) K for data collection. The length of the cylindrical crystal was not estimated, but it exceeded the diameter of the collimator (0.35 mm).
The methyl H atoms are disordered and modelled as two sets of idealized positions. All H atoms were placed geometrically and allowed to refine with independent isotropic displacement parameters (one common parameter for all methyl H atoms). The methyl groups were allowed to rotate about its local threefold axis. Friedel pairs (486) were merged prior to merging in P212121; the reported value of Rint corresponds to subsequent merging of equivalent reflections in this space group.
Data collection: COLLECT (Nonius, 1998); cell refinement: HKL SCALEPACK (Otwinowski & Minor, 1997); data reduction: HKL DENZO (Otwinowski & Minor 1997) and SCALEPACK; program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); software used to prepare material for publication: SHELXL97.
C6H7N | Dx = 1.117 Mg m−3 |
Mr = 93.13 | Melting point: 206.3 K |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.7107 Å |
a = 6.6593 (5) Å | Cell parameters from 4571 reflections |
b = 7.0878 (6) Å | θ = 1.0–27.5° |
c = 11.7358 (7) Å | µ = 0.07 mm−1 |
V = 553.93 (7) Å3 | T = 120 K |
Z = 4 | Cylinder, colourless |
F(000) = 200 | 0.15 mm (radius) |
Nonius KappaCCD diffractometer | Rint = 0.110 |
Radiation source: fine-focus sealed tube | θmax = 27.5°, θmin = 3.5° |
Thin–slice ω and ϕ scans | h = −4→8 |
3477 measured reflections | k = −9→7 |
749 independent reflections | l = −15→10 |
672 reflections with I > 2σ(I) |
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)] = 0.062 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.181 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.10 | w = 1/[σ2(Fo2) + (0.1425P)2] where P = (Fo2 + 2Fc2)/3 |
749 reflections | (Δ/σ)max < 0.001 |
71 parameters | Δρmax = 0.29 e Å−3 |
0 restraints | Δρmin = −0.29 e Å−3 |
C6H7N | V = 553.93 (7) Å3 |
Mr = 93.13 | Z = 4 |
Orthorhombic, P212121 | Mo Kα radiation |
a = 6.6593 (5) Å | µ = 0.07 mm−1 |
b = 7.0878 (6) Å | T = 120 K |
c = 11.7358 (7) Å | 0.15 mm (radius) |
Nonius KappaCCD diffractometer | 672 reflections with I > 2σ(I) |
3477 measured reflections | Rint = 0.110 |
749 independent reflections |
R[F2 > 2σ(F2)] = 0.062 | 0 restraints |
wR(F2) = 0.181 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.10 | Δρmax = 0.29 e Å−3 |
749 reflections | Δρmin = −0.29 e Å−3 |
71 parameters |
Experimental. Grown in situ in a 0.3 mm Lindemann capillary tube at 206 K. Freidel pairs (486) were averaged for the refinement. |
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. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
N1 | 0.3417 (3) | 0.0686 (3) | 0.05357 (16) | 0.0301 (5) | |
C2 | 0.4756 (3) | −0.0479 (3) | 0.10232 (18) | 0.0275 (6) | |
C3 | 0.4444 (4) | −0.1249 (3) | 0.2101 (2) | 0.0335 (6) | |
H3 | 0.5432 | −0.2040 | 0.2437 | 0.071 (12)* | |
C4 | 0.2683 (4) | −0.0852 (3) | 0.26800 (19) | 0.0382 (6) | |
H4 | 0.2440 | −0.1368 | 0.3414 | 0.067 (10)* | |
C5 | 0.1293 (4) | 0.0306 (3) | 0.2168 (2) | 0.0356 (6) | |
H5 | 0.0061 | 0.0592 | 0.2539 | 0.048 (8)* | |
C6 | 0.1716 (4) | 0.1045 (3) | 0.1109 (2) | 0.0337 (6) | |
H6 | 0.0751 | 0.1852 | 0.0765 | 0.038 (7)* | |
C7 | 0.6606 (4) | −0.0923 (4) | 0.0342 (2) | 0.0408 (7) | 0.80 |
H7A | 0.7359 | 0.0242 | 0.0201 | 0.060 (7)* | 0.80 |
H7B | 0.6217 | −0.1490 | −0.0386 | 0.060 (7)* | 0.80 |
H7C | 0.7449 | −0.1810 | 0.0768 | 0.060 (7)* | 0.80 |
C7' | 0.6606 (4) | −0.0923 (4) | 0.0342 (2) | 0.0408 (7) | 0.20 |
H7A' | 0.6776 | 0.0026 | −0.0257 | 0.060 (7)* | 0.20 |
H7B' | 0.6468 | −0.2174 | −0.0004 | 0.060 (7)* | 0.20 |
H7C' | 0.7781 | −0.0910 | 0.0845 | 0.060 (7)* | 0.20 |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0279 (9) | 0.0357 (10) | 0.0268 (9) | −0.0009 (9) | −0.0039 (7) | 0.0014 (7) |
C2 | 0.0274 (10) | 0.0255 (9) | 0.0295 (10) | −0.0020 (9) | −0.0028 (9) | −0.0017 (8) |
C3 | 0.0391 (12) | 0.0275 (11) | 0.0339 (11) | 0.0009 (9) | −0.0076 (10) | 0.0032 (8) |
C4 | 0.0492 (14) | 0.0361 (12) | 0.0293 (11) | −0.0055 (12) | 0.0022 (10) | 0.0033 (10) |
C5 | 0.0308 (11) | 0.0399 (12) | 0.0360 (12) | −0.0027 (10) | 0.0050 (9) | −0.0041 (10) |
C6 | 0.0255 (10) | 0.0352 (11) | 0.0405 (12) | 0.0005 (10) | −0.0036 (10) | 0.0033 (10) |
C7 | 0.0321 (11) | 0.0448 (13) | 0.0456 (14) | 0.0058 (11) | 0.0036 (11) | −0.0012 (11) |
C7' | 0.0321 (11) | 0.0448 (13) | 0.0456 (14) | 0.0058 (11) | 0.0036 (11) | −0.0012 (11) |
N1—C6 | 1.341 (3) | C4—H4 | 0.9500 |
N1—C2 | 1.343 (3) | C5—C6 | 1.379 (3) |
C2—C3 | 1.394 (3) | C5—H5 | 0.9500 |
C2—C7 | 1.502 (3) | C6—H6 | 0.9500 |
C3—C4 | 1.384 (3) | C7—H7A | 0.9800 |
C3—H3 | 0.9500 | C7—H7B | 0.9800 |
C4—C5 | 1.375 (4) | C7—H7C | 0.9800 |
C6—N1—C2 | 117.6 (2) | C4—C5—C6 | 118.9 (2) |
N1—C2—C3 | 121.9 (2) | C4—C5—H5 | 120.6 |
N1—C2—C7 | 116.5 (2) | C6—C5—H5 | 120.6 |
C3—C2—C7 | 121.6 (2) | N1—C6—C5 | 123.6 (2) |
C4—C3—C2 | 119.5 (2) | N1—C6—H6 | 118.2 |
C4—C3—H3 | 120.3 | C5—C6—H6 | 118.2 |
C2—C3—H3 | 120.3 | C2—C7—H7A | 109.5 |
C5—C4—C3 | 118.5 (2) | C2—C7—H7B | 109.5 |
C5—C4—H4 | 120.7 | C2—C7—H7C | 109.5 |
C3—C4—H4 | 120.7 | ||
C6—N1—C2—C3 | −2.1 (3) | C2—C3—C4—C5 | −0.3 (3) |
C6—N1—C2—C7 | 177.44 (18) | C3—C4—C5—C6 | −0.8 (4) |
N1—C2—C3—C4 | 1.8 (3) | C2—N1—C6—C5 | 0.9 (3) |
C7—C2—C3—C4 | −177.7 (2) | C4—C5—C6—N1 | 0.5 (4) |
Experimental details
Crystal data | |
Chemical formula | C6H7N |
Mr | 93.13 |
Crystal system, space group | Orthorhombic, P212121 |
Temperature (K) | 120 |
a, b, c (Å) | 6.6593 (5), 7.0878 (6), 11.7358 (7) |
V (Å3) | 553.93 (7) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.07 |
Crystal size (mm) | 0.15 (radius) |
Data collection | |
Diffractometer | Nonius KappaCCD diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 3477, 749, 672 |
Rint | 0.110 |
(sin θ/λ)max (Å−1) | 0.649 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.062, 0.181, 1.10 |
No. of reflections | 749 |
No. of parameters | 71 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.29, −0.29 |
Computer programs: COLLECT (Nonius, 1998), HKL SCALEPACK (Otwinowski & Minor, 1997), HKL DENZO (Otwinowski & Minor 1997) and SCALEPACK, SIR92 (Altomare et al., 1994), SHELXL97 (Sheldrick, 1997), SHELXL97.
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The picolines (methylpyridines) comprise a series of empirical formula C6H7N, with weak intermolecular interactions and low melting points. The crystal structure of 4-picoline (4-methylpyridine; m.p. 276 K) has been determined previously from a crystal grown using an elaborate modified Bridgman technique (Ohms et al., 1985). We report here the crystal structure of 2-picoline (m.p. 206 K), determined at 120 (2) K from a crystal grown in situ in a 0.3 mm glass capillary. This work forms part of a study devoted to improving techniques for determining the crystal structures of substances that are liquids at room temperature (see, for example, Bond & Davies, 2001).
Molecules of (I) (Fig. 1) pack in a herring-bone-type arrangement (Fig. 2) in the non-centrosymmetric space group P212121. Between molecules, C—H···N contacts exist that are close to linear [H4···N1i = 2.60 Å and C4—H4···N1i = 146.6°; H6···N1ii = 2.79 Å and C6—H6···N1ii = 170.1°; symmetry codes: (i) 0.5 - x, -y, 0.5 + z; (ii) -0.5 + x, -y, -z], indicative of directional hydrogen bonds.