Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536801018396/cf6121sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536801018396/cf6121Isup2.hkl |
CCDC reference: 177193
Key indicators
- Single-crystal X-ray study
- T = 180 K
- Mean (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
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
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.
C8H11N | Dx = 1.049 Mg m−3 |
Mr = 121.18 | Melting point: 230 K |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 8.7773 (5) Å | Cell parameters from 16950 reflections |
b = 20.3849 (11) Å | θ = 1.0–25.0° |
c = 8.9935 (4) Å | µ = 0.06 mm−1 |
β = 107.427 (3)° | T = 180 K |
V = 1535.29 (14) Å3 | Cylinder, colourless |
Z = 8 | 0.15 mm (radius) |
F(000) = 528 |
Nonius KappaCCD diffractometer | 2056 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.069 |
Thin slice ω and φ scans | θmax = 25.1°, θmin = 3.8° |
Absorption correction: multi-scan (SORTAV; Blessing, 1995) | h = −10→10 |
Tmin = 0.796, Tmax = 0.955 | k = −24→24 |
11768 measured reflections | l = −10→10 |
2701 independent reflections |
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)] = 0.071 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.193 | H-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 parameters | Δρmax = 0.21 e Å−3 |
0 restraints | Δρmin = −0.19 e Å−3 |
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. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
N1A | 1.3594 (2) | 0.91500 (9) | 1.1117 (2) | 0.0369 (5) | |
C2A | 1.2878 (3) | 0.91572 (11) | 0.9567 (3) | 0.0372 (6) | |
C3A | 1.1226 (3) | 0.91440 (11) | 0.8918 (3) | 0.0386 (6) | |
H3A | 1.0765 | 0.9144 | 0.7818 | 0.051 (4)* | |
C4A | 1.0248 (3) | 0.91311 (10) | 0.9885 (3) | 0.0392 (6) | |
C5A | 1.1001 (3) | 0.91222 (11) | 1.1481 (3) | 0.0397 (6) | |
H5A | 1.0381 | 0.9109 | 1.2184 | 0.051 (4)* | |
C6A | 1.2649 (3) | 0.91317 (11) | 1.2051 (3) | 0.0375 (6) | |
C7A | 1.3977 (3) | 0.91774 (14) | 0.8560 (3) | 0.0517 (7) | |
H7AA | 1.4762 | 0.8823 | 0.8866 | 0.098 (3)* | |
H7BA | 1.4531 | 0.9601 | 0.8694 | 0.098 (3)* | |
H7CA | 1.3350 | 0.9122 | 0.7465 | 0.098 (3)* | |
C8A | 0.8456 (3) | 0.91212 (13) | 0.9243 (3) | 0.0510 (7) | |
H8AA | 0.8013 | 0.9501 | 0.9639 | 0.098 (3)* | |
H8BA | 0.8044 | 0.8717 | 0.9570 | 0.098 (3)* | |
H8CA | 0.8144 | 0.9140 | 0.8103 | 0.098 (3)* | |
C9A | 1.3493 (3) | 0.91192 (14) | 1.3778 (3) | 0.0519 (7) | |
H9AA | 1.4208 | 0.8739 | 1.4029 | 0.098 (3)* | |
H9BA | 1.2702 | 0.9088 | 1.4347 | 0.098 (3)* | |
H9CA | 1.4117 | 0.9522 | 1.4081 | 0.098 (3)* | |
N1B | 0.9841 (2) | 0.85586 (9) | 0.4930 (2) | 0.0411 (5) | |
C2B | 1.0232 (3) | 0.79541 (11) | 0.4565 (3) | 0.0416 (6) | |
C3B | 0.9255 (3) | 0.75946 (12) | 0.3343 (3) | 0.0445 (6) | |
H3B | 0.9590 | 0.7174 | 0.3107 | 0.051 (4)* | |
C4B | 0.7790 (3) | 0.78423 (12) | 0.2460 (3) | 0.0419 (6) | |
C5B | 0.7392 (3) | 0.84653 (12) | 0.2841 (3) | 0.0399 (6) | |
H5B | 0.6404 | 0.8657 | 0.2268 | 0.051 (4)* | |
C6B | 0.8433 (3) | 0.88085 (12) | 0.4059 (3) | 0.0392 (6) | |
C7B | 1.1806 (3) | 0.76838 (14) | 0.5575 (4) | 0.0578 (8) | |
H7AB | 1.2513 | 0.8047 | 0.6055 | 0.098 (3)* | |
H7BB | 1.2306 | 0.7423 | 0.4932 | 0.098 (3)* | |
H7CB | 1.1619 | 0.7405 | 0.6391 | 0.098 (3)* | |
C8B | 0.6669 (4) | 0.74532 (16) | 0.1172 (3) | 0.0609 (8) | |
H8AB | 0.5869 | 0.7747 | 0.0504 | 0.098 (3)* | 0.49 (4) |
H8BB | 0.6133 | 0.7120 | 0.1621 | 0.098 (3)* | 0.49 (4) |
H8CB | 0.7273 | 0.7239 | 0.0552 | 0.098 (3)* | 0.49 (4) |
H8DB | 0.6980 | 0.6990 | 0.1281 | 0.098 (3)* | 0.51 (4) |
H8EB | 0.6717 | 0.7618 | 0.0164 | 0.098 (3)* | 0.51 (4) |
H8FB | 0.5577 | 0.7498 | 0.1233 | 0.098 (3)* | 0.51 (4) |
C9B | 0.8038 (3) | 0.94906 (13) | 0.4465 (4) | 0.0578 (8) | |
H9AB | 0.8214 | 0.9521 | 0.5592 | 0.098 (3)* | |
H9BB | 0.6917 | 0.9588 | 0.3914 | 0.098 (3)* | |
H9CB | 0.8726 | 0.9807 | 0.4155 | 0.098 (3)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1A | 0.0324 (11) | 0.0377 (11) | 0.0391 (11) | 0.0020 (8) | 0.0084 (8) | 0.0019 (8) |
C2A | 0.0332 (12) | 0.0376 (13) | 0.0395 (13) | 0.0005 (10) | 0.0088 (10) | 0.0040 (9) |
C3A | 0.0349 (13) | 0.0386 (13) | 0.0389 (13) | 0.0009 (10) | 0.0059 (10) | 0.0048 (10) |
C4A | 0.0325 (13) | 0.0306 (12) | 0.0522 (14) | −0.0004 (9) | 0.0091 (11) | 0.0029 (10) |
C5A | 0.0372 (13) | 0.0376 (13) | 0.0470 (14) | 0.0013 (10) | 0.0165 (11) | 0.0010 (10) |
C6A | 0.0373 (13) | 0.0340 (12) | 0.0411 (13) | 0.0010 (9) | 0.0116 (10) | 0.0011 (9) |
C7A | 0.0413 (15) | 0.0690 (18) | 0.0474 (15) | 0.0037 (13) | 0.0174 (12) | 0.0062 (13) |
C8A | 0.0293 (13) | 0.0515 (16) | 0.0681 (18) | −0.0022 (11) | 0.0084 (12) | 0.0052 (12) |
C9A | 0.0490 (16) | 0.0683 (18) | 0.0378 (14) | 0.0018 (13) | 0.0123 (12) | −0.0027 (12) |
N1B | 0.0346 (11) | 0.0420 (11) | 0.0449 (11) | 0.0024 (9) | 0.0091 (9) | 0.0061 (9) |
C2B | 0.0324 (13) | 0.0397 (13) | 0.0512 (14) | 0.0013 (10) | 0.0103 (11) | 0.0071 (11) |
C3B | 0.0377 (14) | 0.0423 (14) | 0.0536 (15) | 0.0012 (11) | 0.0140 (12) | −0.0014 (11) |
C4B | 0.0354 (13) | 0.0512 (15) | 0.0403 (13) | −0.0016 (11) | 0.0133 (11) | −0.0007 (10) |
C5B | 0.0308 (12) | 0.0525 (15) | 0.0364 (12) | 0.0050 (10) | 0.0101 (10) | 0.0082 (10) |
C6B | 0.0332 (13) | 0.0427 (13) | 0.0428 (13) | 0.0043 (10) | 0.0131 (10) | 0.0079 (10) |
C7B | 0.0397 (16) | 0.0497 (16) | 0.0745 (19) | 0.0076 (12) | 0.0028 (14) | 0.0085 (13) |
C8B | 0.0492 (17) | 0.074 (2) | 0.0540 (16) | −0.0015 (14) | 0.0078 (13) | −0.0152 (14) |
C9B | 0.0476 (17) | 0.0473 (16) | 0.074 (2) | 0.0065 (13) | 0.0116 (14) | −0.0012 (13) |
N1A—C6A | 1.345 (3) | C2B—C3B | 1.384 (3) |
N1A—C2A | 1.347 (3) | C2B—C7B | 1.512 (3) |
C2A—C3A | 1.392 (3) | C3B—C4B | 1.388 (3) |
C2A—C7A | 1.508 (3) | C3B—H3B | 0.950 |
C3A—C4A | 1.393 (3) | C4B—C5B | 1.387 (3) |
C3A—H3A | 0.950 | C4B—C8B | 1.502 (4) |
C4A—C5A | 1.389 (3) | C5B—C6B | 1.387 (3) |
C4A—C8A | 1.505 (3) | C5B—H5B | 0.950 |
C5A—C6A | 1.383 (3) | C6B—C9B | 1.504 (4) |
C5A—H5A | 0.950 | C7B—H7AB | 0.980 |
C6A—C9A | 1.508 (3) | C7B—H7BB | 0.980 |
C7A—H7AA | 0.980 | C7B—H7CB | 0.980 |
C7A—H7BA | 0.980 | C8B—H8AB | 0.980 |
C7A—H7CA | 0.980 | C8B—H8BB | 0.980 |
C8A—H8AA | 0.980 | C8B—H8CB | 0.980 |
C8A—H8BA | 0.980 | C8B—H8DB | 0.980 |
C8A—H8CA | 0.980 | C8B—H8EB | 0.980 |
C9A—H9AA | 0.980 | C8B—H8FB | 0.980 |
C9A—H9BA | 0.980 | C9B—H9AB | 0.980 |
C9A—H9CA | 0.980 | C9B—H9BB | 0.980 |
N1B—C2B | 1.346 (3) | C9B—H9CB | 0.980 |
N1B—C6B | 1.349 (3) | ||
C6A—N1A—C2A | 117.6 (2) | C5B—C4B—C8B | 121.2 (2) |
N1A—C2A—C3A | 122.5 (2) | C3B—C4B—C8B | 122.0 (2) |
N1A—C2A—C7A | 116.0 (2) | C4B—C5B—C6B | 120.1 (2) |
C3A—C2A—C7A | 121.5 (2) | C4B—C5B—H5B | 120.0 |
C2A—C3A—C4A | 119.9 (2) | C6B—C5B—H5B | 120.0 |
C2A—C3A—H3A | 120.1 | N1B—C6B—C5B | 122.7 (2) |
C4A—C3A—H3A | 120.1 | N1B—C6B—C9B | 116.5 (2) |
C5A—C4A—C3A | 117.0 (2) | C5B—C6B—C9B | 120.8 (2) |
C5A—C4A—C8A | 121.0 (2) | C2B—C7B—H7AB | 109.5 |
C3A—C4A—C8A | 121.9 (2) | C2B—C7B—H7BB | 109.5 |
C6A—C5A—C4A | 120.2 (2) | H7AB—C7B—H7BB | 109.5 |
C6A—C5A—H5A | 119.9 | C2B—C7B—H7CB | 109.5 |
C4A—C5A—H5A | 119.9 | H7AB—C7B—H7CB | 109.5 |
N1A—C6A—C5A | 122.8 (2) | H7BB—C7B—H7CB | 109.5 |
N1A—C6A—C9A | 116.1 (2) | C4B—C8B—H8AB | 109.5 |
C5A—C6A—C9A | 121.2 (2) | C4B—C8B—H8BB | 109.5 |
C2A—C7A—H7AA | 109.5 | H8AB—C8B—H8BB | 109.5 |
C2A—C7A—H7BA | 109.5 | C4B—C8B—H8CB | 109.5 |
H7AA—C7A—H7BA | 109.5 | H8AB—C8B—H8CB | 109.5 |
C2A—C7A—H7CA | 109.5 | H8BB—C8B—H8CB | 109.5 |
H7AA—C7A—H7CA | 109.5 | C4B—C8B—H8DB | 109.5 |
H7BA—C7A—H7CA | 109.5 | H8AB—C8B—H8DB | 141.1 |
C4A—C8A—H8AA | 109.5 | H8BB—C8B—H8DB | 56.3 |
C4A—C8A—H8BA | 109.5 | H8CB—C8B—H8DB | 56.3 |
H8AA—C8A—H8BA | 109.5 | C4B—C8B—H8EB | 109.5 |
C4A—C8A—H8CA | 109.5 | H8AB—C8B—H8EB | 56.3 |
H8AA—C8A—H8CA | 109.5 | H8BB—C8B—H8EB | 141.1 |
H8BA—C8A—H8CA | 109.5 | H8CB—C8B—H8EB | 56.3 |
C6A—C9A—H9AA | 109.5 | H8DB—C8B—H8EB | 109.5 |
C6A—C9A—H9BA | 109.5 | C4B—C8B—H8FB | 109.5 |
H9AA—C9A—H9BA | 109.5 | H8AB—C8B—H8FB | 56.3 |
C6A—C9A—H9CA | 109.5 | H8BB—C8B—H8FB | 56.3 |
H9AA—C9A—H9CA | 109.5 | H8CB—C8B—H8FB | 141.1 |
H9BA—C9A—H9CA | 109.5 | H8DB—C8B—H8FB | 109.5 |
C2B—N1B—C6B | 117.4 (2) | H8EB—C8B—H8FB | 109.5 |
N1B—C2B—C3B | 122.4 (2) | C6B—C9B—H9AB | 109.5 |
N1B—C2B—C7B | 116.2 (2) | C6B—C9B—H9BB | 109.5 |
C3B—C2B—C7B | 121.4 (2) | H9AB—C9B—H9BB | 109.5 |
C2B—C3B—C4B | 120.6 (2) | C6B—C9B—H9CB | 109.5 |
C2B—C3B—H3B | 119.7 | H9AB—C9B—H9CB | 109.5 |
C4B—C3B—H3B | 119.7 | H9BB—C9B—H9CB | 109.5 |
C5B—C4B—C3B | 116.8 (2) | ||
C6A—N1A—C2A—C3A | −0.3 (3) | C6B—N1B—C2B—C3B | 0.4 (3) |
C6A—N1A—C2A—C7A | −180.0 (2) | C6B—N1B—C2B—C7B | −179.2 (2) |
N1A—C2A—C3A—C4A | 0.8 (3) | N1B—C2B—C3B—C4B | −1.7 (4) |
C7A—C2A—C3A—C4A | −179.5 (2) | C7B—C2B—C3B—C4B | 177.9 (2) |
C2A—C3A—C4A—C5A | −1.0 (3) | C2B—C3B—C4B—C5B | 1.6 (4) |
C2A—C3A—C4A—C8A | 179.6 (2) | C2B—C3B—C4B—C8B | −177.3 (2) |
C3A—C4A—C5A—C6A | 0.5 (3) | C3B—C4B—C5B—C6B | −0.3 (3) |
C8A—C4A—C5A—C6A | −180.0 (2) | C8B—C4B—C5B—C6B | 178.6 (2) |
C2A—N1A—C6A—C5A | −0.2 (3) | C2B—N1B—C6B—C5B | 1.0 (3) |
C2A—N1A—C6A—C9A | 179.6 (2) | C2B—N1B—C6B—C9B | −178.7 (2) |
C4A—C5A—C6A—N1A | 0.0 (3) | C4B—C5B—C6B—N1B | −1.0 (3) |
C4A—C5A—C6A—C9A | −179.7 (2) | C4B—C5B—C6B—C9B | 178.6 (2) |
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