2,4,6-Trimethyl­pyridine-3,5-dicarbonitrile

The title compound, C₁₀H₉N₃, is essently planar, except for the methyl H atoms. The asymmetric unit consists of two molecules. In the crystal structure, weak intra­molecular C—H...N hydrogen-bonding inter­actions occur, linking the mol­ecules into chains propagating along the a axis.

Key indicators

• Single-crystal X-ray study
• T = 292 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.059
• wR factor = 0.164
• Data-to-parameter ratio = 17.8

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C11    -   C16     ..       6.85 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C13    -   C18     ..       5.33 su
PLAT371_ALERT_2_C Long   C(sp2)-C(sp1) Bond  C1     -   C6     ...       1.43 Ang.
PLAT371_ALERT_2_C Long   C(sp2)-C(sp1) Bond  C3     -   C8     ...       1.44 Ang.
PLAT371_ALERT_2_C Long   C(sp2)-C(sp1) Bond  C11    -   C16    ...       1.44 Ang.
PLAT371_ALERT_2_C Long   C(sp2)-C(sp1) Bond  C13    -   C18    ...       1.44 Ang.

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   7 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   6 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

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Computing details

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.

2,4,6-Trimethylpyridine-3,5-dicarbonitrile

Crystal data

C10H9N3	F(000) = 720
Mr = 171.20	Dx = 1.208 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2307 reflections
a = 15.4261 (17) Å	θ = 2.7–22.7°
b = 8.0266 (9) Å	µ = 0.08 mm^−1
c = 16.6153 (19) Å	T = 292 K
β = 113.802 (2)°	Block, colourless
V = 1882.3 (4) Å^3	0.30 × 0.20 × 0.10 mm
Z = 8

Data collection

Bruker SMART CCD area-detector diffractometer	4297 independent reflections
Radiation source: fine-focus sealed tube	2170 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.097
φ and ω scans	θmax = 27.5°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −19→20
Tmin = 0.978, Tmax = 0.992	k = −10→10
19228 measured reflections	l = −21→21

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.059	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.164	H-atom parameters constrained
S = 0.90	w = 1/[σ^2(Fo^2) + (0.0795P)^2] where P = (Fo^2 + 2Fc^2)/3
4297 reflections	(Δ/σ)max = 0.034
241 parameters	Δρmax = 0.21 e Å^−3
0 restraints	Δρmin = −0.18 e Å^−3

Special details

Experimental. ¹H NMR (CDCl₃, p.p.m.): d 2.70 (s, 3H), 2.76 (s, 6H). ¹³C NMR (CDCl₃, p.p.m.): d 19.8, 24.4, 108.3, 114.7, 145.9, and 164.3. Anal. Calcd for C₁₀H₉N₃ (%): C, 70.71; H, 5.41; N, 24.39. Found (%): C, 70.16; H, 5.3; N, 24.54.

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 (Ų)

	x	y	z	Uiso*/Ueq
C1	1.01217 (14)	0.2741 (2)	0.03255 (13)	0.0493 (5)
C2	1.07121 (13)	0.3295 (2)	0.11575 (12)	0.0480 (5)
C3	1.02753 (12)	0.4186 (2)	0.16128 (12)	0.0478 (5)
C4	0.93003 (13)	0.4494 (2)	0.12340 (12)	0.0485 (5)
C5	0.91483 (14)	0.3068 (2)	−0.00224 (12)	0.0510 (5)
C6	1.05179 (16)	0.1805 (3)	−0.01805 (14)	0.0632 (6)
C7	1.17555 (13)	0.2945 (3)	0.15518 (14)	0.0681 (6)
H7A	1.1862	0.1806	0.1742	0.102*
H7B	1.2063	0.3667	0.2046	0.102*
H7C	1.2010	0.3139	0.1119	0.102*
C8	1.08406 (14)	0.4798 (3)	0.24828 (15)	0.0604 (6)
C9	0.88195 (15)	0.5461 (3)	0.17070 (14)	0.0688 (6)
H9A	0.8686	0.6568	0.1470	0.103*
H9B	0.9226	0.5516	0.2322	0.103*
H9C	0.8238	0.4918	0.1633	0.103*
C10	0.84881 (16)	0.2436 (3)	−0.09035 (13)	0.0724 (7)
H10A	0.8143	0.1496	−0.0828	0.109*
H10B	0.8845	0.2105	−0.1235	0.109*
H10C	0.8051	0.3302	−0.1214	0.109*
C11	0.49919 (14)	0.4157 (2)	0.14443 (13)	0.0519 (5)
C12	0.44905 (13)	0.3366 (2)	0.06488 (13)	0.0496 (5)
C13	0.50347 (14)	0.2699 (2)	0.02335 (12)	0.0493 (5)
C14	0.60198 (14)	0.2819 (2)	0.06067 (14)	0.0532 (5)
C15	0.59798 (15)	0.4283 (3)	0.17871 (13)	0.0564 (5)
C16	0.44750 (17)	0.4867 (3)	0.19165 (16)	0.0728 (7)
C17	0.34348 (13)	0.3225 (3)	0.02521 (14)	0.0645 (6)
H17A	0.3207	0.3259	−0.0377	0.097*
H17B	0.3168	0.4135	0.0450	0.097*
H17C	0.3252	0.2191	0.0428	0.097*
C18	0.45718 (16)	0.1849 (3)	−0.05931 (15)	0.0620 (6)
C19	0.66179 (15)	0.2052 (3)	0.01870 (16)	0.0745 (7)
H19A	0.7204	0.2651	0.0364	0.112*
H19B	0.6288	0.2103	−0.0441	0.112*
H19C	0.6746	0.0911	0.0368	0.112*
C20	0.65342 (17)	0.5166 (3)	0.26293 (14)	0.0800 (7)
H20A	0.7185	0.4821	0.2848	0.120*
H20B	0.6280	0.4898	0.3054	0.120*
H20C	0.6495	0.6346	0.2529	0.120*
N1	0.87586 (10)	0.3951 (2)	0.04283 (10)	0.0537 (5)
N2	1.08474 (17)	0.1052 (3)	−0.05664 (15)	0.0924 (7)
N3	1.12874 (15)	0.5306 (3)	0.31635 (14)	0.0873 (7)
N4	0.64776 (11)	0.3611 (2)	0.13705 (11)	0.0602 (5)
N5	0.40463 (16)	0.5415 (3)	0.22746 (16)	0.1052 (8)
N6	0.42047 (15)	0.1177 (3)	−0.12460 (14)	0.0916 (7)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0565 (12)	0.0469 (12)	0.0490 (12)	−0.0033 (9)	0.0261 (10)	0.0046 (9)
C2	0.0466 (11)	0.0498 (12)	0.0490 (12)	−0.0034 (9)	0.0208 (9)	0.0089 (9)
C3	0.0437 (11)	0.0525 (12)	0.0450 (11)	−0.0054 (9)	0.0157 (9)	0.0033 (9)
C4	0.0484 (11)	0.0530 (12)	0.0460 (12)	−0.0042 (9)	0.0211 (10)	0.0058 (9)
C5	0.0568 (13)	0.0504 (12)	0.0436 (11)	−0.0087 (10)	0.0180 (10)	0.0060 (9)
C6	0.0802 (16)	0.0579 (14)	0.0603 (14)	−0.0021 (12)	0.0375 (13)	0.0051 (11)
C7	0.0488 (12)	0.0844 (17)	0.0715 (15)	0.0037 (11)	0.0248 (11)	0.0086 (13)
C8	0.0513 (12)	0.0735 (15)	0.0527 (13)	−0.0062 (11)	0.0171 (11)	−0.0026 (12)
C9	0.0610 (13)	0.0895 (17)	0.0592 (14)	0.0084 (12)	0.0277 (11)	0.0031 (12)
C10	0.0747 (15)	0.0775 (16)	0.0521 (13)	−0.0132 (13)	0.0123 (11)	−0.0035 (11)
C11	0.0570 (13)	0.0528 (12)	0.0513 (12)	0.0037 (10)	0.0274 (10)	0.0077 (10)
C12	0.0527 (12)	0.0481 (12)	0.0495 (12)	0.0032 (9)	0.0222 (10)	0.0110 (10)
C13	0.0558 (12)	0.0483 (12)	0.0460 (12)	−0.0031 (9)	0.0226 (10)	0.0054 (9)
C14	0.0554 (13)	0.0533 (12)	0.0554 (13)	−0.0037 (10)	0.0271 (11)	0.0069 (10)
C15	0.0635 (14)	0.0573 (13)	0.0473 (12)	−0.0074 (11)	0.0211 (11)	0.0040 (10)
C16	0.0757 (16)	0.0780 (17)	0.0678 (16)	0.0017 (13)	0.0324 (13)	−0.0065 (13)
C17	0.0536 (13)	0.0710 (15)	0.0702 (15)	0.0051 (11)	0.0263 (11)	0.0081 (12)
C18	0.0672 (14)	0.0622 (14)	0.0576 (14)	−0.0033 (12)	0.0261 (12)	0.0025 (12)
C19	0.0688 (15)	0.0824 (17)	0.0864 (17)	−0.0073 (13)	0.0460 (13)	−0.0078 (14)
C20	0.0817 (16)	0.0947 (19)	0.0595 (15)	−0.0180 (14)	0.0242 (13)	−0.0100 (13)
N1	0.0461 (9)	0.0637 (11)	0.0474 (10)	−0.0036 (8)	0.0148 (8)	0.0053 (8)
N2	0.1230 (18)	0.0841 (16)	0.0917 (16)	0.0098 (14)	0.0656 (15)	−0.0016 (12)
N3	0.0760 (14)	0.1138 (18)	0.0617 (13)	−0.0174 (12)	0.0169 (11)	−0.0176 (12)
N4	0.0564 (11)	0.0685 (12)	0.0589 (11)	−0.0083 (9)	0.0265 (9)	0.0020 (9)
N5	0.1040 (18)	0.122 (2)	0.1078 (19)	0.0046 (15)	0.0614 (16)	−0.0307 (15)
N6	0.0988 (16)	0.1009 (17)	0.0687 (14)	−0.0148 (13)	0.0271 (13)	−0.0156 (13)

Geometric parameters (Å, º)

C1—C2	1.386 (3)	C11—C12	1.387 (3)
C1—C5	1.399 (3)	C11—C15	1.399 (3)
C1—C6	1.435 (3)	C11—C16	1.443 (3)
C2—C3	1.396 (2)	C12—C13	1.391 (3)
C2—C7	1.499 (3)	C12—C17	1.494 (3)
C3—C4	1.398 (3)	C13—C14	1.394 (3)
C3—C8	1.440 (3)	C13—C18	1.438 (3)
C4—N1	1.333 (2)	C14—N4	1.338 (2)
C4—C9	1.497 (3)	C14—C19	1.495 (3)
C5—N1	1.337 (2)	C15—N4	1.337 (3)
C5—C10	1.495 (3)	C15—C20	1.492 (3)
C6—N2	1.139 (3)	C16—N5	1.141 (3)
C7—H7A	0.9600	C17—H17A	0.9600
C7—H7B	0.9600	C17—H17B	0.9600
C7—H7C	0.9600	C17—H17C	0.9600
C8—N3	1.136 (3)	C18—N6	1.137 (3)
C9—H9A	0.9600	C19—H19A	0.9600
C9—H9B	0.9600	C19—H19B	0.9600
C9—H9C	0.9600	C19—H19C	0.9600
C10—H10A	0.9600	C20—H20A	0.9600
C10—H10B	0.9600	C20—H20B	0.9600
C10—H10C	0.9600	C20—H20C	0.9600
C2—C1—C5	121.03 (19)	C12—C11—C16	118.75 (19)
C2—C1—C6	119.22 (18)	C15—C11—C16	120.0 (2)
C5—C1—C6	119.74 (19)	C11—C12—C13	115.65 (18)
C1—C2—C3	115.98 (17)	C11—C12—C17	123.00 (18)
C1—C2—C7	122.22 (18)	C13—C12—C17	121.35 (18)
C3—C2—C7	121.80 (18)	C12—C13—C14	121.37 (18)
C2—C3—C4	120.89 (17)	C12—C13—C18	119.31 (18)
C2—C3—C8	119.31 (17)	C14—C13—C18	119.31 (19)
C4—C3—C8	119.80 (18)	N4—C14—C13	121.21 (19)
N1—C4—C3	121.23 (18)	N4—C14—C19	116.68 (18)
N1—C4—C9	117.01 (17)	C13—C14—C19	122.10 (19)
C3—C4—C9	121.75 (18)	N4—C15—C11	121.25 (19)
N1—C5—C1	121.22 (18)	N4—C15—C20	116.46 (19)
N1—C5—C10	116.46 (18)	C11—C15—C20	122.3 (2)
C1—C5—C10	122.3 (2)	N5—C16—C11	178.4 (3)
N2—C6—C1	178.6 (3)	C12—C17—H17A	109.5
C2—C7—H7A	109.5	C12—C17—H17B	109.5
C2—C7—H7B	109.5	H17A—C17—H17B	109.5
H7A—C7—H7B	109.5	C12—C17—H17C	109.5
C2—C7—H7C	109.5	H17A—C17—H17C	109.5
H7A—C7—H7C	109.5	H17B—C17—H17C	109.5
H7B—C7—H7C	109.5	N6—C18—C13	179.9 (3)
N3—C8—C3	178.8 (3)	C14—C19—H19A	109.5
C4—C9—H9A	109.5	C14—C19—H19B	109.5
C4—C9—H9B	109.5	H19A—C19—H19B	109.5
H9A—C9—H9B	109.5	C14—C19—H19C	109.5
C4—C9—H9C	109.5	H19A—C19—H19C	109.5
H9A—C9—H9C	109.5	H19B—C19—H19C	109.5
H9B—C9—H9C	109.5	C15—C20—H20A	109.5
C5—C10—H10A	109.5	C15—C20—H20B	109.5
C5—C10—H10B	109.5	H20A—C20—H20B	109.5
H10A—C10—H10B	109.5	C15—C20—H20C	109.5
C5—C10—H10C	109.5	H20A—C20—H20C	109.5
H10A—C10—H10C	109.5	H20B—C20—H20C	109.5
H10B—C10—H10C	109.5	C4—N1—C5	119.62 (16)
C12—C11—C15	121.22 (18)	C15—N4—C14	119.28 (17)
C5—C1—C2—C3	−0.1 (3)	C11—C12—C13—C14	0.5 (3)
C6—C1—C2—C3	−179.52 (17)	C17—C12—C13—C14	−179.49 (18)
C5—C1—C2—C7	179.22 (18)	C11—C12—C13—C18	179.70 (17)
C6—C1—C2—C7	−0.2 (3)	C17—C12—C13—C18	−0.3 (3)
C1—C2—C3—C4	−0.5 (3)	C12—C13—C14—N4	−1.4 (3)
C7—C2—C3—C4	−179.81 (18)	C18—C13—C14—N4	179.40 (18)
C1—C2—C3—C8	179.76 (17)	C12—C13—C14—C19	177.61 (18)
C7—C2—C3—C8	0.4 (3)	C18—C13—C14—C19	−1.6 (3)
C2—C3—C4—N1	−0.1 (3)	C12—C11—C15—N4	−1.6 (3)
C8—C3—C4—N1	179.69 (17)	C16—C11—C15—N4	178.81 (19)
C2—C3—C4—C9	−179.38 (18)	C12—C11—C15—C20	178.34 (19)
C8—C3—C4—C9	0.4 (3)	C16—C11—C15—C20	−1.2 (3)
C2—C1—C5—N1	1.3 (3)	C3—C4—N1—C5	1.2 (3)
C6—C1—C5—N1	−179.30 (18)	C9—C4—N1—C5	−179.41 (18)
C2—C1—C5—C10	−177.76 (17)	C1—C5—N1—C4	−1.8 (3)
C6—C1—C5—C10	1.7 (3)	C10—C5—N1—C4	177.25 (17)
C15—C11—C12—C13	1.0 (3)	C11—C15—N4—C14	0.7 (3)
C16—C11—C12—C13	−179.46 (18)	C20—C15—N4—C14	−179.25 (19)
C15—C11—C12—C17	−179.07 (19)	C13—C14—N4—C15	0.7 (3)
C16—C11—C12—C17	0.5 (3)	C19—C14—N4—C15	−178.29 (18)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C19—H19A···N1	0.96	2.58	3.510 (3)	164
C19—H19A···N1	0.96	2.58	3.510 (3)	164