2-Chloro-4-(3,5-di­methyl-1H-pyrazol-1-yl)­pyrimidine

In the crystal structure of the title compound, C₉H₉ClN₄, there are non-classical intramolecular C—H...N hydrogen bonds and intermolecular C—H...π interactions.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.036
• wR factor = 0.106
• Data-to-parameter ratio = 10.7

checkCIF/PLATON results

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Computing details

Data collection: SMART (Bruker, 1998); cell refinement: SMART; data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1999); software used to prepare material for publication: SHELXTL.

2-chloro-4-(3,5-dimethyl-1H-pyrazol-1-yl)pyrimidine

Crystal data

C9H9ClN4	F(000) = 216
Mr = 208.65	Dx = 1.425 Mg m^−3
Monoclinic, P21/m	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yb	Cell parameters from 571 reflections
a = 7.336 (4) Å	θ = 3.1–26.2°
b = 6.607 (4) Å	µ = 0.36 mm^−1
c = 10.092 (6) Å	T = 293 K
β = 96.387 (9)°	Block, yellow
V = 486.1 (5) Å^3	0.32 × 0.26 × 0.18 mm
Z = 2

Data collection

Bruker SMART CCD area-detector diffractometer	934 independent reflections
Radiation source: fine-focus sealed tube	713 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.024
φ and ω scans	θmax = 25.0°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −7→8
Tmin = 0.895, Tmax = 0.938	k = −7→7
2461 measured reflections	l = −10→12

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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.106	H-atom parameters constrained
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0615P)^2 + 0.096P] where P = (Fo^2 + 2Fc^2)/3
934 reflections	(Δ/σ)max < 0.001
87 parameters	Δρmax = 0.17 e Å^−3
0 restraints	Δρmin = −0.19 e Å^−3

Special details

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	Occ. (<1)
Cl1	0.54090 (11)	0.2500	−0.33176 (8)	0.0745 (4)
N1	0.8951 (3)	0.2500	−0.2946 (2)	0.0418 (6)
N2	0.7348 (3)	0.2500	−0.1014 (2)	0.0383 (6)
N3	0.8894 (3)	0.2500	0.1140 (2)	0.0333 (5)
N4	1.0561 (3)	0.2500	0.1931 (2)	0.0379 (6)
C1	0.7489 (4)	0.2500	−0.2308 (3)	0.0405 (7)
C2	1.0521 (4)	0.2500	−0.2135 (3)	0.0404 (7)
H2	1.1615	0.2500	−0.2521	0.048*
C3	1.0620 (4)	0.2500	−0.0777 (3)	0.0365 (6)
H3	1.1736	0.2500	−0.0241	0.044*
C4	0.8947 (3)	0.2500	−0.0241 (2)	0.0305 (6)
C5	0.5453 (4)	0.2500	0.1383 (3)	0.0515 (8)
H5A	0.5112	0.1184	0.1036	0.077*	0.50
H5B	0.5239	0.3487	0.0685	0.077*	0.50
H5C	0.4732	0.2829	0.2091	0.077*	0.50
C6	0.7436 (4)	0.2500	0.1905 (3)	0.0362 (6)
C7	0.8213 (4)	0.2500	0.3191 (3)	0.0420 (7)
H7	0.7599	0.2500	0.3949	0.050*
C8	1.0133 (4)	0.2500	0.3157 (3)	0.0398 (7)
C9	1.1595 (4)	0.2500	0.4310 (3)	0.0555 (9)
H9A	1.1219	0.1666	0.5009	0.083*	0.50
H9B	1.1794	0.3858	0.4631	0.083*	0.50
H9C	1.2711	0.1976	0.4030	0.083*	0.50

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0420 (5)	0.1337 (9)	0.0442 (5)	0.000	−0.0108 (4)	0.000
N1	0.0403 (13)	0.0500 (14)	0.0354 (13)	0.000	0.0054 (11)	0.000
N2	0.0319 (12)	0.0482 (14)	0.0346 (12)	0.000	0.0033 (10)	0.000
N3	0.0340 (12)	0.0354 (12)	0.0300 (12)	0.000	0.0006 (9)	0.000
N4	0.0321 (12)	0.0450 (14)	0.0351 (12)	0.000	−0.0031 (9)	0.000
C1	0.0358 (15)	0.0505 (17)	0.0338 (15)	0.000	−0.0026 (12)	0.000
C2	0.0338 (15)	0.0470 (17)	0.0417 (16)	0.000	0.0105 (12)	0.000
C3	0.0291 (14)	0.0407 (16)	0.0398 (16)	0.000	0.0043 (11)	0.000
C4	0.0328 (13)	0.0271 (13)	0.0312 (13)	0.000	0.0024 (11)	0.000
C5	0.0349 (15)	0.072 (2)	0.0499 (17)	0.000	0.0138 (14)	0.000
C6	0.0363 (14)	0.0356 (14)	0.0380 (15)	0.000	0.0107 (12)	0.000
C7	0.0467 (17)	0.0464 (17)	0.0343 (15)	0.000	0.0114 (13)	0.000
C8	0.0466 (16)	0.0407 (16)	0.0315 (15)	0.000	0.0023 (12)	0.000
C9	0.057 (2)	0.073 (2)	0.0354 (16)	0.000	−0.0021 (15)	0.000

Geometric parameters (Å, º)

Cl1—C1	1.738 (3)	C3—H3	0.9300
N1—C1	1.311 (4)	C5—C6	1.491 (4)
N1—C2	1.337 (3)	C5—H5A	0.9600
N2—C1	1.322 (4)	C5—H5B	0.9600
N2—C4	1.335 (3)	C5—H5C	0.9600
N3—N4	1.384 (3)	C6—C7	1.358 (4)
N3—C6	1.387 (3)	C7—C8	1.413 (4)
N3—C4	1.398 (3)	C7—H7	0.9300
N4—C8	1.310 (3)	C8—C9	1.492 (4)
C2—C3	1.364 (4)	C9—H9A	0.9600
C2—H2	0.9300	C9—H9B	0.9600
C3—C4	1.395 (4)	C9—H9C	0.9600
C1—N1—C2	113.3 (2)	H5A—C5—H5B	109.5
C1—N2—C4	114.7 (2)	C6—C5—H5C	109.5
N4—N3—C6	111.4 (2)	H5A—C5—H5C	109.5
N4—N3—C4	117.0 (2)	H5B—C5—H5C	109.5
C6—N3—C4	131.6 (2)	C7—C6—N3	105.3 (2)
C8—N4—N3	104.8 (2)	C7—C6—C5	128.8 (3)
N1—C1—N2	130.0 (2)	N3—C6—C5	125.8 (2)
N1—C1—Cl1	115.2 (2)	C6—C7—C8	106.9 (2)
N2—C1—Cl1	114.8 (2)	C6—C7—H7	126.6
N1—C2—C3	124.1 (2)	C8—C7—H7	126.6
N1—C2—H2	117.9	N4—C8—C7	111.5 (2)
C3—C2—H2	117.9	N4—C8—C9	120.7 (3)
C2—C3—C4	116.0 (2)	C7—C8—C9	127.8 (2)
C2—C3—H3	122.0	C8—C9—H9A	109.5
C4—C3—H3	122.0	C8—C9—H9B	109.5
N2—C4—C3	121.8 (2)	H9A—C9—H9B	109.5
N2—C4—N3	117.6 (2)	C8—C9—H9C	109.5
C3—C4—N3	120.7 (2)	H9A—C9—H9C	109.5
C6—C5—H5A	109.5	H9B—C9—H9C	109.5
C6—C5—H5B	109.5
C6—N3—N4—C8	0.0	C6—N3—C4—N2	0.0
C4—N3—N4—C8	180.0	N4—N3—C4—C3	0.0
C2—N1—C1—N2	0.0	C6—N3—C4—C3	180.0
C2—N1—C1—Cl1	180.0	N4—N3—C6—C7	0.0
C4—N2—C1—N1	0.0	C4—N3—C6—C7	180.0
C4—N2—C1—Cl1	180.0	N4—N3—C6—C5	180.0
C1—N1—C2—C3	0.0	C4—N3—C6—C5	0.0
N1—C2—C3—C4	0.0	N3—C6—C7—C8	0.0
C1—N2—C4—C3	0.0	C5—C6—C7—C8	180.0
C1—N2—C4—N3	180.0	N3—N4—C8—C7	0.0
C2—C3—C4—N2	0.0	N3—N4—C8—C9	180.0
C2—C3—C4—N3	180.0	C6—C7—C8—N4	0.0
N4—N3—C4—N2	180.0	C6—C7—C8—C9	180.0

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5B···N2	0.96	2.52	2.921 (4)	105