Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802003380/cf6153sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536802003380/cf6153Isup2.hkl |
CCDC reference: 182637
Key indicators
- Single-crystal X-ray study
- T = 150 K
- Mean (C-C) = 0.002 Å
- R factor = 0.054
- wR factor = 0.145
- Data-to-parameter ratio = 18.2
checkCIF results
No syntax errors found ADDSYM reports no extra symmetry
The sample (99%) was obtained from the Lancaster company and used without further purification. The crystal was grown in a 0.3 mm glass capillary tube at ca 236 K (a temperature only slightly less than the melting point of the solid in the capillary tube) using a technique described earlier (Davies & Bond, 2001). Once grown, the crystal was cooled to 150 (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).
H atoms were placed geometrically and refined with isotropic displacement parameters, with common parameters assigned to chemically equivalent H atoms (one parameter for all methyl H atoms, four parameters in total). Both methyl groups are disordered and were modelled as two sets of positions, each position rotated at 60° from the other about the local threefold axis.
Data collection: COLLECT (Nonius, 1998); cell refinement: HKL 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.
C7H9N | F(000) = 232 |
Mr = 107.15 | Dx = 1.113 Mg m−3 |
Triclinic, P1 | Melting point: 258 K |
a = 7.0991 (4) Å | Mo Kα radiation, λ = 0.7107 Å |
b = 7.7279 (5) Å | Cell parameters from 2259 reflections |
c = 12.3900 (9) Å | θ = 1.0–22.5° |
α = 108.139 (4)° | µ = 0.07 mm−1 |
β = 92.399 (4)° | T = 150 K |
γ = 96.743 (5)° | Cylinder, colourless |
V = 639.26 (7) Å3 | 0.15 mm (radius) |
Z = 4 |
Nonius KappaCCD diffractometer | Rint = 0.030 |
Radiation source: fine-focus sealed tube | θmax = 27.5°, θmin = 3.7° |
Thin–slice ω and ϕ scans | h = 0→9 |
4192 measured reflections | k = −9→9 |
2827 independent reflections | l = −15→15 |
1643 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)] = 0.054 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.145 | H-atom parameters constrained |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0487P)2 + 0.1043P] where P = (Fo2 + 2Fc2)/3 |
2827 reflections | (Δ/σ)max < 0.001 |
155 parameters | Δρmax = 0.14 e Å−3 |
0 restraints | Δρmin = −0.13 e Å−3 |
C7H9N | γ = 96.743 (5)° |
Mr = 107.15 | V = 639.26 (7) Å3 |
Triclinic, P1 | Z = 4 |
a = 7.0991 (4) Å | Mo Kα radiation |
b = 7.7279 (5) Å | µ = 0.07 mm−1 |
c = 12.3900 (9) Å | T = 150 K |
α = 108.139 (4)° | 0.15 mm (radius) |
β = 92.399 (4)° |
Nonius KappaCCD diffractometer | 1643 reflections with I > 2σ(I) |
4192 measured reflections | Rint = 0.030 |
2827 independent reflections |
R[F2 > 2σ(F2)] = 0.054 | 0 restraints |
wR(F2) = 0.145 | H-atom parameters constrained |
S = 1.03 | Δρmax = 0.14 e Å−3 |
2827 reflections | Δρmin = −0.13 e Å−3 |
155 parameters |
Experimental. Crystal grown in situ in a 0.3 mm Lindemann tube at 236 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) 2.5016 (0.0055) x + 6.8487 (0.0029) y - 3.1884 (0.0079) z = 5.0267 (0.0020) * 0.0014 (0.0008) N1A * -0.0015 (0.0011) C2A * 0.0002 (0.0011) C3A * 0.0011 (0.0011) C4A * -0.0012 (0.0008) C5A Rms deviation of fitted atoms = 0.0012 - 2.8000 (0.0048) x + 6.0639 (0.0036) y + 3.6076 (0.0076) z = 6.5009 (0.0039) Angle to previous plane (with approximate e.s.d.) = 54.07 (0.05) * -0.0029 (0.0008) N1B * 0.0034 (0.0011) C2B * -0.0010 (0.0010) C3B * -0.0018 (0.0011) C4B * 0.0023 (0.0008) C5B Rms deviation of fitted atoms = 0.0024 |
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) | |
N1A | 0.25742 (19) | 0.81270 (19) | 0.37067 (12) | 0.0456 (4) | |
C2A | 0.4063 (2) | 0.7350 (2) | 0.32155 (15) | 0.0405 (4) | |
C3A | 0.4134 (2) | 0.6780 (2) | 0.20418 (15) | 0.0423 (4) | |
H3A | 0.5197 | 0.6240 | 0.1713 | 0.053 (2)* | |
C4A | 0.2674 (2) | 0.6995 (2) | 0.13545 (14) | 0.0399 (4) | |
H4A | 0.2726 | 0.6605 | 0.0551 | 0.053 (2)* | |
C5A | 0.1135 (2) | 0.7775 (2) | 0.18304 (14) | 0.0393 (4) | |
C6A | 0.1162 (2) | 0.8312 (2) | 0.30039 (15) | 0.0429 (4) | |
H6A | 0.0106 | 0.8851 | 0.3342 | 0.053 (2)* | |
C7A | 0.5634 (2) | 0.7155 (3) | 0.40036 (16) | 0.0541 (5) | |
H7AA | 0.5118 | 0.6406 | 0.4460 | 0.060 (2)* | 0.768 (18) |
H7AB | 0.6188 | 0.8374 | 0.4510 | 0.060 (2)* | 0.768 (18) |
H7AC | 0.6620 | 0.6558 | 0.3555 | 0.060 (2)* | 0.768 (18) |
H7AD | 0.6833 | 0.7820 | 0.3890 | 0.060 (2)* | 0.232 (18) |
H7AE | 0.5762 | 0.5851 | 0.3839 | 0.060 (2)* | 0.232 (18) |
H7AF | 0.5331 | 0.7667 | 0.4795 | 0.060 (2)* | 0.232 (18) |
C8A | −0.0512 (2) | 0.8010 (3) | 0.11044 (16) | 0.0562 (5) | |
H8AA | −0.0027 | 0.8536 | 0.0529 | 0.060 (2)* | 0.638 (17) |
H8AB | −0.1309 | 0.8836 | 0.1587 | 0.060 (2)* | 0.638 (17) |
H8AC | −0.1271 | 0.6811 | 0.0725 | 0.060 (2)* | 0.638 (17) |
H8AD | −0.1712 | 0.7585 | 0.1365 | 0.060 (2)* | 0.362 (17) |
H8AE | −0.0429 | 0.7286 | 0.0307 | 0.060 (2)* | 0.362 (17) |
H8AF | −0.0467 | 0.9311 | 0.1169 | 0.060 (2)* | 0.362 (17) |
N1B | 0.26955 (18) | 0.69075 (19) | 0.84937 (12) | 0.0430 (4) | |
C2B | 0.4229 (2) | 0.7806 (2) | 0.81909 (13) | 0.0358 (4) | |
C3B | 0.4128 (2) | 0.8328 (2) | 0.72224 (14) | 0.0401 (4) | |
H3B | 0.5225 | 0.8950 | 0.7022 | 0.053 (2)* | |
C4B | 0.2446 (2) | 0.7952 (2) | 0.65465 (14) | 0.0380 (4) | |
H4B | 0.2381 | 0.8313 | 0.5881 | 0.053 (2)* | |
C5B | 0.0858 (2) | 0.7052 (2) | 0.68387 (13) | 0.0368 (4) | |
C6B | 0.1067 (2) | 0.6566 (2) | 0.78164 (14) | 0.0409 (4) | |
H6B | −0.0019 | 0.5943 | 0.8027 | 0.053 (2)* | |
C7B | 0.6037 (2) | 0.8188 (2) | 0.89500 (15) | 0.0510 (5) | |
H7BA | 0.5774 | 0.7867 | 0.9640 | 0.060 (2)* | 0.593 (18) |
H7BB | 0.6540 | 0.9495 | 0.9161 | 0.060 (2)* | 0.593 (18) |
H7BC | 0.6975 | 0.7449 | 0.8544 | 0.060 (2)* | 0.593 (18) |
H7BD | 0.7086 | 0.8674 | 0.8591 | 0.060 (2)* | 0.407 (18) |
H7BE | 0.6319 | 0.7046 | 0.9069 | 0.060 (2)* | 0.407 (18) |
H7BF | 0.5885 | 0.9092 | 0.9686 | 0.060 (2)* | 0.407 (18) |
C8B | −0.1029 (2) | 0.6634 (2) | 0.61414 (15) | 0.0520 (5) | |
H8BA | −0.0871 | 0.6974 | 0.5449 | 0.060 (2)* | 0.627 (18) |
H8BB | −0.1952 | 0.7338 | 0.6590 | 0.060 (2)* | 0.627 (18) |
H8BC | −0.1490 | 0.5317 | 0.5933 | 0.060 (2)* | 0.627 (18) |
H8BD | −0.2005 | 0.6112 | 0.6532 | 0.060 (2)* | 0.373 (18) |
H8BE | −0.0924 | 0.5748 | 0.5391 | 0.060 (2)* | 0.373 (18) |
H8BF | −0.1385 | 0.7769 | 0.6048 | 0.060 (2)* | 0.373 (18) |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1A | 0.0508 (8) | 0.0478 (8) | 0.0395 (9) | 0.0071 (6) | 0.0022 (7) | 0.0160 (7) |
C2A | 0.0431 (8) | 0.0389 (9) | 0.0415 (10) | 0.0036 (7) | 0.0002 (7) | 0.0166 (8) |
C3A | 0.0448 (8) | 0.0414 (9) | 0.0434 (11) | 0.0072 (7) | 0.0097 (8) | 0.0161 (8) |
C4A | 0.0507 (9) | 0.0398 (9) | 0.0285 (9) | 0.0001 (7) | 0.0036 (7) | 0.0120 (7) |
C5A | 0.0430 (8) | 0.0371 (9) | 0.0389 (10) | −0.0004 (7) | −0.0016 (7) | 0.0163 (7) |
C6A | 0.0452 (9) | 0.0446 (10) | 0.0423 (11) | 0.0093 (7) | 0.0057 (8) | 0.0172 (8) |
C7A | 0.0528 (10) | 0.0615 (12) | 0.0510 (12) | 0.0093 (9) | −0.0058 (9) | 0.0229 (10) |
C8A | 0.0534 (10) | 0.0613 (12) | 0.0542 (13) | 0.0063 (9) | −0.0096 (9) | 0.0213 (10) |
N1B | 0.0452 (7) | 0.0484 (8) | 0.0388 (9) | 0.0069 (6) | 0.0030 (6) | 0.0187 (7) |
C2B | 0.0387 (8) | 0.0335 (8) | 0.0341 (9) | 0.0080 (6) | 0.0023 (7) | 0.0083 (7) |
C3B | 0.0395 (8) | 0.0399 (9) | 0.0437 (11) | 0.0047 (7) | 0.0082 (7) | 0.0171 (8) |
C4B | 0.0470 (8) | 0.0417 (9) | 0.0312 (9) | 0.0122 (7) | 0.0068 (7) | 0.0174 (7) |
C5B | 0.0385 (8) | 0.0353 (9) | 0.0354 (10) | 0.0088 (7) | 0.0014 (7) | 0.0085 (7) |
C6B | 0.0383 (8) | 0.0423 (9) | 0.0432 (11) | 0.0026 (7) | 0.0057 (7) | 0.0161 (8) |
C7B | 0.0445 (9) | 0.0537 (11) | 0.0502 (12) | 0.0084 (8) | −0.0061 (8) | 0.0106 (9) |
C8B | 0.0452 (9) | 0.0546 (11) | 0.0509 (12) | 0.0111 (8) | −0.0069 (8) | 0.0089 (9) |
N1A—C6A | 1.350 (2) | N1B—C6B | 1.3489 (19) |
N1A—C2A | 1.350 (2) | N1B—C2B | 1.352 (2) |
C2A—C3A | 1.387 (2) | C2B—C3B | 1.382 (2) |
C2A—C7A | 1.503 (2) | C2B—C7B | 1.5018 (19) |
C3A—C4A | 1.372 (2) | C3B—C4B | 1.377 (2) |
C3A—H3A | 0.950 | C3B—H3B | 0.950 |
C4A—C5A | 1.376 (2) | C4B—C5B | 1.376 (2) |
C4A—H4A | 0.950 | C4B—H4B | 0.950 |
C5A—C6A | 1.381 (2) | C5B—C6B | 1.383 (2) |
C5A—C8A | 1.508 (2) | C5B—C8B | 1.5074 (19) |
C6A—H6A | 0.950 | C6B—H6B | 0.950 |
C7A—H7AA | 0.980 | C7B—H7BA | 0.980 |
C7A—H7AB | 0.980 | C7B—H7BB | 0.980 |
C7A—H7AC | 0.980 | C7B—H7BC | 0.980 |
C7A—H7AD | 0.980 | C7B—H7BD | 0.980 |
C7A—H7AE | 0.980 | C7B—H7BE | 0.980 |
C7A—H7AF | 0.980 | C7B—H7BF | 0.980 |
C8A—H8AA | 0.980 | C8B—H8BA | 0.980 |
C8A—H8AB | 0.980 | C8B—H8BB | 0.980 |
C8A—H8AC | 0.980 | C8B—H8BC | 0.980 |
C8A—H8AD | 0.980 | C8B—H8BD | 0.980 |
C8A—H8AE | 0.980 | C8B—H8BE | 0.980 |
C8A—H8AF | 0.980 | C8B—H8BF | 0.980 |
C6A—N1A—C2A | 116.96 (15) | C6B—N1B—C2B | 117.02 (15) |
N1A—C2A—C3A | 121.25 (15) | N1B—C2B—C3B | 121.16 (13) |
N1A—C2A—C7A | 116.68 (16) | N1B—C2B—C7B | 116.79 (15) |
C3A—C2A—C7A | 122.06 (15) | C3B—C2B—C7B | 122.05 (15) |
C4A—C3A—C2A | 120.14 (15) | C4B—C3B—C2B | 120.38 (15) |
C4A—C3A—H3A | 119.9 | C4B—C3B—H3B | 119.8 |
C2A—C3A—H3A | 119.9 | C2B—C3B—H3B | 119.8 |
C3A—C4A—C5A | 119.91 (16) | C5B—C4B—C3B | 119.72 (16) |
C3A—C4A—H4A | 120.0 | C5B—C4B—H4B | 120.1 |
C5A—C4A—H4A | 120.0 | C3B—C4B—H4B | 120.1 |
C4A—C5A—C6A | 116.77 (15) | C4B—C5B—C6B | 116.69 (14) |
C4A—C5A—C8A | 121.58 (16) | C4B—C5B—C8B | 121.98 (16) |
C6A—C5A—C8A | 121.65 (15) | C6B—C5B—C8B | 121.33 (15) |
N1A—C6A—C5A | 124.96 (15) | N1B—C6B—C5B | 125.02 (15) |
N1A—C6A—H6A | 117.5 | N1B—C6B—H6B | 117.5 |
C5A—C6A—H6A | 117.5 | C5B—C6B—H6B | 117.5 |
C2A—C7A—H7AA | 109.5 | C2B—C7B—H7BA | 109.5 |
C2A—C7A—H7AB | 109.5 | C2B—C7B—H7BB | 109.5 |
H7AA—C7A—H7AB | 109.5 | H7BA—C7B—H7BB | 109.5 |
C2A—C7A—H7AC | 109.5 | C2B—C7B—H7BC | 109.5 |
H7AA—C7A—H7AC | 109.5 | H7BA—C7B—H7BC | 109.5 |
H7AB—C7A—H7AC | 109.5 | H7BB—C7B—H7BC | 109.5 |
C2A—C7A—H7AD | 109.5 | C2B—C7B—H7BD | 109.5 |
C2A—C7A—H7AE | 109.5 | C2B—C7B—H7BE | 109.5 |
H7AD—C7A—H7AE | 109.5 | H7BD—C7B—H7BE | 109.5 |
C2A—C7A—H7AF | 109.5 | C2B—C7B—H7BF | 109.5 |
H7AD—C7A—H7AF | 109.5 | H7BD—C7B—H7BF | 109.5 |
H7AE—C7A—H7AF | 109.5 | H7BE—C7B—H7BF | 109.5 |
C5A—C8A—H8AA | 109.5 | C5B—C8B—H8BA | 109.5 |
C5A—C8A—H8AB | 109.5 | C5B—C8B—H8BB | 109.5 |
H8AA—C8A—H8AB | 109.5 | H8BA—C8B—H8BB | 109.5 |
C5A—C8A—H8AC | 109.5 | C5B—C8B—H8BC | 109.5 |
H8AA—C8A—H8AC | 109.5 | H8BA—C8B—H8BC | 109.5 |
H8AB—C8A—H8AC | 109.5 | H8BB—C8B—H8BC | 109.5 |
C5A—C8A—H8AD | 109.5 | C5B—C8B—H8BD | 109.5 |
C5A—C8A—H8AE | 109.5 | C5B—C8B—H8BE | 109.5 |
H8AD—C8A—H8AE | 109.5 | H8BD—C8B—H8BE | 109.5 |
C5A—C8A—H8AF | 109.5 | C5B—C8B—H8BF | 109.5 |
H8AD—C8A—H8AF | 109.5 | H8BD—C8B—H8BF | 109.5 |
H8AE—C8A—H8AF | 109.5 | H8BE—C8B—H8BF | 109.5 |
C6A—N1A—C2A—C3A | 0.4 (2) | C6B—N1B—C2B—C3B | −0.7 (2) |
C6A—N1A—C2A—C7A | 179.80 (15) | C6B—N1B—C2B—C7B | 179.83 (14) |
N1A—C2A—C3A—C4A | −0.2 (3) | N1B—C2B—C3B—C4B | 0.5 (2) |
C7A—C2A—C3A—C4A | −179.60 (16) | C7B—C2B—C3B—C4B | 179.92 (14) |
C2A—C3A—C4A—C5A | −0.1 (2) | C2B—C3B—C4B—C5B | 0.0 (2) |
C3A—C4A—C5A—C6A | 0.1 (2) | C3B—C4B—C5B—C6B | −0.3 (2) |
C3A—C4A—C5A—C8A | −179.07 (15) | C3B—C4B—C5B—C8B | 178.94 (14) |
C2A—N1A—C6A—C5A | −0.3 (3) | C2B—N1B—C6B—C5B | 0.5 (2) |
C4A—C5A—C6A—N1A | 0.1 (3) | C4B—C5B—C6B—N1B | 0.0 (2) |
C8A—C5A—C6A—N1A | 179.26 (16) | C8B—C5B—C6B—N1B | −179.19 (14) |
D—H···A | D—H | H···A | D···A | D—H···A |
C4B—H4B···N1A | 0.95 | 2.66 | 3.567 (2) | 159 |
C4A—H4A···N1Bi | 0.95 | 2.63 | 3.525 (2) | 157 |
Symmetry code: (i) x, y, z−1. |
Experimental details
Crystal data | |
Chemical formula | C7H9N |
Mr | 107.15 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 150 |
a, b, c (Å) | 7.0991 (4), 7.7279 (5), 12.3900 (9) |
α, β, γ (°) | 108.139 (4), 92.399 (4), 96.743 (5) |
V (Å3) | 639.26 (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 | 4192, 2827, 1643 |
Rint | 0.030 |
(sin θ/λ)max (Å−1) | 0.649 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.054, 0.145, 1.03 |
No. of reflections | 2827 |
No. of parameters | 155 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.14, −0.13 |
Computer programs: COLLECT (Nonius, 1998), HKL SCALEPACK (Otwinowski & Minor, 1997), HKL DENZO and SCALEPACK (Otwinowski & Minor, 1997), SIR92 (Altomare et al., 1994), SHELXL97 (Sheldrick, 1997), XP (Sheldrick, 1993) and CAMERON (Watkin et al., 1996), SHELXL97.
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This work forms part of a study devoted to improving the techniques for determining the crystal structures of substances that are liquid at room temperature. We have reported previously the crystal structures of 2,6-lutidine (Bond et al., 2001) and 3,5-lutidine (Bond & Davies, 2002), and report here the structure of the isomer 2,5-lutidine, (I), determined at 150 (2) K following in situ crystal growth from the liquid.
In space group P1, there are two independent molecules of (I) in the asymmetric unit (Fig. 1). Molecules are linked via C—H···N interactions into extended chains [Fig. 2; H4B···N1A = 2.66 Å, C4B—H4B···N1A = 159°; H4A···N1Bi = 2.63 Å and C4A—H4A···N1Bi = 157°; symmetry code: (i) x, y, -1 + z]. Similar chains are observed in the crystal structures of 2,6-lutidine and 3,5-lutidine. Within the chains in (I), adjacent molecules are twisted about the direction of chain propagation with an angle between the least-squares planes through adjacent molecules of 54.0 (1)°. This twist presumably accommodates the steric requirements of the methyl substituents. Adjacent chains are arranged in a parallel manner to give polar sheets parallel to (010) (Fig. 2). Chains in adjacent sheets are arranged in an anti-parallel manner so that the crystal is not macroscopically polar (Fig. 3).