4-{3,5-Dimethyl-4-[(E)-(4-methyl­phen­yl)diazen­yl]-1H-pyrazol-1-yl}benzonitrile

Mol­ecules in the title compound, C₁₉H₁₇N₅, are linked into chains via weak C—H...π(cyano) inter­actions, and these chains are linked via C—H...π(arene) inter­actions to form a three-dimensional structure of parallel sheets.

Key indicators

• Single-crystal X-ray study
• T = 273 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.072
• wR factor = 0.141
• Data-to-parameter ratio = 15.1

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT230_ALERT_2_C Hirshfeld Test Diff for    N5     -   C15     ..       5.05 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C1     -   C7      ..       5.10 su
PLAT371_ALERT_2_C Long   C(sp2)-C(sp1) Bond  C1     -   C7     ...       1.44 Ang.

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

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 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, 2001); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in SHELXTL/PC (Sheldrick, 1994); software used to prepare material for publication: PLATON (Spek, 2003) and Mercury (Macrae et al., 2006).

4-{3,5-Dimethyl-4-[(E)-(4-methylphenyl)diazenyl]-1H-pyrazol-1-yl}benzonitrile

Crystal data

C19H17N5	Z = 2
Mr = 315.38	F(000) = 332
Triclinic, P1	Dx = 1.279 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.3464 (18) Å	Cell parameters from 632 reflections
b = 9.4021 (18) Å	θ = 2.1–26.4°
c = 10.422 (2) Å	µ = 0.08 mm^−1
α = 108.580 (3)°	T = 273 K
β = 98.301 (4)°	Plate, orange
γ = 103.722 (4)°	0.45 × 0.13 × 0.06 mm
V = 818.9 (3) Å^3

Data collection

Bruker SMART CCD area-detector diffractometer	Rint = 0.046
φ and ω scans	θmax = 26.4°, θmin = 2.1°
6660 measured reflections	h = −11→11
3312 independent reflections	k = −11→11
1932 reflections with I > 2σ(I)	l = −13→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)] = 0.072	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.141	H-atom parameters constrained
S = 1.02	w = 1/[σ^2(Fo^2) + (0.0414P)^2] where P = (Fo^2 + 2Fc^2)/3
3312 reflections	(Δ/σ)max = 0.011
220 parameters	Δρmax = 0.19 e Å^−3
0 restraints	Δρmin = −0.13 e Å^−3

Special details

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F² for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > σ(F²) is used only for calculating -R-factor-obs 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
N1	0.6651 (3)	0.8449 (4)	1.3463 (3)	0.0949 (14)
N2	0.7970 (2)	0.6548 (3)	0.7017 (2)	0.0466 (8)
N3	0.9120 (2)	0.7625 (3)	0.6813 (2)	0.0506 (8)
N4	0.7662 (2)	0.4340 (3)	0.3516 (2)	0.0493 (9)
N5	0.8331 (2)	0.4728 (3)	0.2666 (2)	0.0505 (9)
C1	0.7153 (3)	0.7760 (3)	1.1005 (3)	0.0483 (11)
C2	0.8591 (3)	0.8320 (3)	1.0820 (3)	0.0489 (10)
C3	0.8843 (3)	0.7907 (3)	0.9504 (3)	0.0451 (10)
C4	0.7676 (3)	0.6938 (3)	0.8364 (3)	0.0412 (10)
C5	0.6222 (3)	0.6424 (3)	0.8545 (3)	0.0510 (10)
C6	0.5977 (3)	0.6814 (3)	0.9860 (3)	0.0485 (10)
C7	0.6867 (3)	0.8151 (4)	1.2374 (4)	0.0632 (11)
C8	1.0285 (3)	0.7830 (3)	0.4919 (3)	0.0656 (12)
C9	0.9164 (3)	0.6974 (3)	0.5505 (3)	0.0472 (11)
C10	0.8065 (3)	0.5478 (3)	0.4858 (3)	0.0439 (10)
C11	0.7337 (3)	0.5245 (3)	0.5854 (3)	0.0453 (10)
C12	0.6109 (3)	0.3810 (3)	0.5722 (3)	0.0610 (11)
C13	0.6815 (3)	0.0924 (3)	−0.0359 (3)	0.0535 (11)
C14	0.7177 (3)	0.1950 (3)	0.0998 (3)	0.0491 (11)
C15	0.7907 (3)	0.3529 (3)	0.1308 (3)	0.0427 (10)
C16	0.8279 (3)	0.4020 (3)	0.0261 (3)	0.0489 (10)
C17	0.7911 (3)	0.2965 (4)	−0.1089 (3)	0.0525 (11)
C18	0.7158 (3)	0.1391 (4)	−0.1433 (3)	0.0515 (11)
C19	0.6741 (4)	0.0239 (4)	−0.2916 (3)	0.0775 (14)
H2	0.93830	0.89750	1.15860	0.0590*
H3	0.98070	0.82840	0.93820	0.0540*
H5	0.54180	0.58170	0.77750	0.0610*
H6	0.50120	0.64400	0.99820	0.0580*
H8A	1.08910	0.88160	0.56310	0.0980*
H8B	0.97580	0.80210	0.41590	0.0980*
H8C	1.09280	0.72070	0.45900	0.0980*
H12A	0.62650	0.36120	0.65720	0.0910*
H12B	0.61400	0.29190	0.49650	0.0910*
H12C	0.51390	0.39800	0.55440	0.0910*
H13	0.63170	−0.01320	−0.05630	0.0640*
H14	0.69370	0.15930	0.16990	0.0590*
H16	0.87840	0.50740	0.04650	0.0590*
H17	0.81750	0.33180	−0.17860	0.0630*
H19A	0.74410	−0.03650	−0.30330	0.1160*
H19B	0.67840	0.08040	−0.35390	0.1160*
H19C	0.57320	−0.04540	−0.31190	0.1160*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.076 (2)	0.121 (3)	0.072 (2)	0.0077 (19)	0.0313 (18)	0.025 (2)
N2	0.0430 (14)	0.0440 (15)	0.0477 (15)	0.0087 (12)	0.0110 (11)	0.0132 (12)
N3	0.0484 (14)	0.0430 (14)	0.0551 (16)	0.0059 (12)	0.0134 (12)	0.0165 (13)
N4	0.0475 (15)	0.0521 (15)	0.0481 (15)	0.0158 (12)	0.0123 (12)	0.0173 (13)
N5	0.0497 (15)	0.0490 (15)	0.0535 (16)	0.0158 (12)	0.0151 (12)	0.0180 (13)
C1	0.0472 (18)	0.0472 (18)	0.0522 (19)	0.0155 (15)	0.0173 (15)	0.0174 (15)
C2	0.0431 (17)	0.0463 (18)	0.0502 (19)	0.0086 (14)	0.0068 (14)	0.0141 (15)
C3	0.0374 (16)	0.0421 (17)	0.0536 (19)	0.0094 (13)	0.0135 (14)	0.0154 (15)
C4	0.0387 (16)	0.0363 (16)	0.0485 (18)	0.0123 (13)	0.0122 (13)	0.0139 (13)
C5	0.0370 (16)	0.0517 (19)	0.0565 (19)	0.0087 (14)	0.0058 (14)	0.0154 (15)
C6	0.0347 (16)	0.0499 (18)	0.063 (2)	0.0103 (14)	0.0153 (15)	0.0237 (16)
C7	0.0506 (19)	0.069 (2)	0.067 (2)	0.0119 (17)	0.0196 (17)	0.023 (2)
C8	0.059 (2)	0.059 (2)	0.068 (2)	0.0042 (16)	0.0142 (17)	0.0196 (17)
C9	0.0426 (17)	0.0505 (19)	0.0508 (19)	0.0147 (15)	0.0129 (14)	0.0203 (15)
C10	0.0414 (16)	0.0433 (17)	0.0459 (18)	0.0124 (14)	0.0084 (13)	0.0163 (14)
C11	0.0414 (16)	0.0394 (17)	0.0513 (18)	0.0095 (14)	0.0053 (14)	0.0162 (15)
C12	0.0584 (19)	0.0524 (19)	0.064 (2)	0.0060 (16)	0.0102 (16)	0.0205 (16)
C13	0.0495 (18)	0.0408 (17)	0.064 (2)	0.0116 (14)	0.0099 (15)	0.0144 (16)
C14	0.0513 (17)	0.0503 (19)	0.0525 (19)	0.0181 (15)	0.0195 (14)	0.0225 (16)
C15	0.0384 (16)	0.0413 (17)	0.0439 (17)	0.0131 (14)	0.0071 (13)	0.0103 (14)
C16	0.0436 (17)	0.0420 (17)	0.058 (2)	0.0093 (14)	0.0098 (14)	0.0180 (16)
C17	0.0536 (18)	0.061 (2)	0.0474 (19)	0.0212 (16)	0.0125 (15)	0.0229 (16)
C18	0.0464 (17)	0.054 (2)	0.0510 (19)	0.0232 (16)	0.0034 (14)	0.0130 (16)
C19	0.087 (3)	0.075 (2)	0.057 (2)	0.028 (2)	0.0109 (19)	0.0069 (19)

Geometric parameters (Å, º)

N1—C7	1.139 (5)	C15—C16	1.371 (4)
N4—N5	1.252 (3)	C16—C17	1.375 (4)
N2—C4	1.418 (3)	C17—C18	1.382 (5)
N2—N3	1.383 (4)	C18—C19	1.508 (4)
N3—C9	1.316 (3)	C2—H2	0.9300
N4—C10	1.395 (4)	C3—H3	0.9300
N5—C15	1.428 (4)	C5—H5	0.9300
C1—C2	1.387 (4)	C6—H6	0.9300
C1—C6	1.380 (4)	C8—H8A	0.9600
C1—C7	1.437 (5)	C8—H8B	0.9600
C2—C3	1.373 (4)	C8—H8C	0.9600
C3—C4	1.377 (4)	C12—H12A	0.9600
C4—C5	1.392 (4)	C12—H12B	0.9600
C5—C6	1.369 (4)	C12—H12C	0.9600
C8—C9	1.489 (4)	C13—H13	0.9300
C9—C10	1.414 (4)	C14—H14	0.9300
C10—C11	1.366 (4)	C16—H16	0.9300
N2—C11	1.350 (4)	C17—H17	0.9300
C11—C12	1.503 (4)	C19—H19A	0.9600
C13—C14	1.372 (4)	C19—H19B	0.9600
C13—C18	1.378 (4)	C19—H19C	0.9600
C14—C15	1.387 (4)
N1···C12^i	3.327 (5)	H3···C13^vii	3.0100
N5···C8	3.037 (4)	H3···C14^vii	2.9500
N1···H12A^i	2.9300	H3···C15^vii	3.0600
N1···H8A^ii	2.7900	H5···C11	2.8800
N3···H3	2.4900	H5···C12	2.6400
N3···H19A^iii	2.7100	H5···H12A	2.4300
N4···H14	2.5300	H5···H12C	2.3500
N4···H5^iv	2.9400	H5···N4^iv	2.9400
N4···H12B	2.6600	H6···C6^i	3.0400
N5···H8B	2.8600	H6···C14^iv	3.0600
N5···H8C	2.8800	H6···C15^iv	2.8700
C5···C12	3.144 (4)	H6···C16^iv	2.9600
C6···C6^i	3.590 (4)	H8A···N1^ii	2.79
C6···C14^iv	3.517 (4)	H8A···C7^ii	3.0000
C6···C15^iv	3.561 (4)	H8B···N5	2.8600
C8···N5	3.037 (4)	H8C···N5	2.8800
C12···N1^i	3.327 (5)	H8C···C10^vii	3.0800
C12···C5	3.144 (4)	H8C···C11^vii	3.0800
C14···C6^iv	3.517 (4)	H12A···C4	2.9400
C15···C6^iv	3.561 (4)	H12A···C5	2.8000
C16···C16^v	3.518 (4)	H12A···C17^vi	3.0000
C2···H16^vi	3.0100	H12A···H5	2.4300
C4···H12A	2.9400	H12A···H17^vi	2.4200
C5···H12A	2.8000	H12A···N1^i	2.93
C5···H13^iii	3.0500	H12B···N4	2.6600
C5···H12C	3.0800	H12B···H19C^ix	2.5300
C6···H13^iii	2.9900	H12C···C5	3.0800
C6···H6^i	3.0400	H12C···H5	2.3500
C7···H8A^ii	3.0000	H12C···C11^iv	2.9200
C10···H8C^vii	3.0800	H12C···H12C^iv	2.5600
C11···H8C^vii	3.0800	H13···C5^x	3.0500
C11···H12C^iv	2.9200	H13···C6^x	2.9900
C11···H5	2.8800	H13···H19C	2.5400
C12···H5	2.6400	H14···N4	2.5300
C13···H3^vii	3.0100	H16···C2^viii	3.0100
C14···H3^vii	2.9500	H16···C16^v	2.9600
C14···H6^iv	3.0600	H16···C17^v	3.0500
C15···H3^vii	3.0600	H17···H12A^viii	2.4200
C15···H6^iv	2.8700	H17···H19B	2.3900
C16···H6^iv	2.9600	H19A···N3^x	2.7100
C16···H16^v	2.9600	H19B···H17	2.3900
C17···H12A^viii	3.0000	H19C···H13	2.5400
C17···H16^v	3.0500	H19C···H12B^ix	2.5300
H3···N3	2.4900
N3—N2—C4	117.5 (2)	C17—C18—C19	121.4 (3)
N3—N2—C11	111.6 (2)	C1—C2—H2	120.00
C4—N2—C11	131.0 (3)	C3—C2—H2	120.00
N2—N3—C9	105.0 (2)	C2—C3—H3	120.00
N5—N4—C10	115.2 (3)	C4—C3—H3	120.00
N4—N5—C15	113.7 (2)	C4—C5—H5	120.00
C2—C1—C6	119.7 (3)	C6—C5—H5	120.00
C2—C1—C7	121.0 (3)	C1—C6—H6	120.00
C6—C1—C7	119.4 (3)	C5—C6—H6	120.00
C1—C2—C3	119.9 (3)	C9—C8—H8A	109.00
C2—C3—C4	120.4 (3)	C9—C8—H8B	109.00
N2—C4—C3	119.0 (3)	C9—C8—H8C	110.00
N2—C4—C5	121.3 (3)	H8A—C8—H8B	109.00
C3—C4—C5	119.7 (3)	H8A—C8—H8C	109.00
C4—C5—C6	119.9 (3)	H8B—C8—H8C	109.00
C1—C6—C5	120.4 (3)	C11—C12—H12A	109.00
N1—C7—C1	179.1 (4)	C11—C12—H12B	109.00
N3—C9—C8	119.6 (3)	C11—C12—H12C	110.00
N3—C9—C10	110.9 (3)	H12A—C12—H12B	109.00
C8—C9—C10	129.6 (3)	H12A—C12—H12C	110.00
N4—C10—C9	133.1 (3)	H12B—C12—H12C	109.00
N4—C10—C11	120.9 (3)	C14—C13—H13	119.00
C9—C10—C11	106.0 (3)	C18—C13—H13	119.00
N2—C11—C10	106.6 (3)	C13—C14—H14	121.00
N2—C11—C12	125.9 (3)	C15—C14—H14	120.00
C10—C11—C12	127.6 (3)	C15—C16—H16	120.00
C14—C13—C18	122.8 (3)	C17—C16—H16	120.00
C13—C14—C15	119.0 (3)	C16—C17—H17	119.00
N5—C15—C14	125.0 (3)	C18—C17—H17	119.00
N5—C15—C16	115.6 (3)	C18—C19—H19A	109.00
C14—C15—C16	119.4 (3)	C18—C19—H19B	109.00
C15—C16—C17	120.5 (3)	C18—C19—H19C	109.00
C16—C17—C18	121.4 (3)	H19A—C19—H19B	110.00
C13—C18—C17	117.0 (3)	H19A—C19—H19C	109.00
C13—C18—C19	121.7 (3)	H19B—C19—H19C	109.00
C4—N2—N3—C9	179.2 (2)	C2—C3—C4—C5	2.4 (4)
C11—N2—N3—C9	1.0 (3)	N2—C4—C5—C6	179.7 (3)
N3—N2—C4—C3	−28.3 (4)	C3—C4—C5—C6	−3.5 (4)
N3—N2—C4—C5	148.5 (3)	C4—C5—C6—C1	2.3 (5)
C11—N2—C4—C3	149.5 (3)	N3—C9—C10—N4	−180.0 (3)
C11—N2—C4—C5	−33.7 (5)	N3—C9—C10—C11	0.0 (3)
N3—N2—C11—C10	−1.0 (3)	C8—C9—C10—N4	−0.2 (6)
N3—N2—C11—C12	177.1 (3)	C8—C9—C10—C11	179.8 (3)
C4—N2—C11—C10	−179.0 (3)	N4—C10—C11—N2	−179.4 (2)
C4—N2—C11—C12	−0.9 (5)	N4—C10—C11—C12	2.5 (5)
N2—N3—C9—C8	179.6 (2)	C9—C10—C11—N2	0.6 (3)
N2—N3—C9—C10	−0.6 (3)	C9—C10—C11—C12	−177.4 (3)
C10—N4—N5—C15	179.2 (2)	C18—C13—C14—C15	0.6 (5)
N5—N4—C10—C9	−4.9 (5)	C14—C13—C18—C17	0.6 (5)
N5—N4—C10—C11	175.1 (3)	C14—C13—C18—C19	−179.8 (3)
N4—N5—C15—C14	−17.4 (4)	C13—C14—C15—N5	179.1 (3)
N4—N5—C15—C16	163.2 (3)	C13—C14—C15—C16	−1.5 (4)
C6—C1—C2—C3	−1.2 (4)	N5—C15—C16—C17	−179.4 (3)
C7—C1—C2—C3	178.8 (3)	C14—C15—C16—C17	1.1 (4)
C2—C1—C6—C5	0.1 (4)	C15—C16—C17—C18	0.2 (5)
C7—C1—C6—C5	−179.9 (3)	C16—C17—C18—C13	−1.0 (4)
C1—C2—C3—C4	0.0 (4)	C16—C17—C18—C19	179.4 (3)
C2—C3—C4—N2	179.3 (3)

Symmetry codes: (i) −x+1, −y+1, −z+2; (ii) −x+2, −y+2, −z+2; (iii) x, y+1, z+1; (iv) −x+1, −y+1, −z+1; (v) −x+2, −y+1, −z; (vi) x, y, z+1; (vii) −x+2, −y+1, −z+1; (viii) x, y, z−1; (ix) −x+1, −y, −z; (x) x, y−1, z−1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···Cg1^iv	0.93	2.82	3.533 (3)	135
C3—H3···Cg2^vii	0.93	2.79	3.464 (3)	131

Symmetry codes: (iv) −x+1, −y+1, −z+1; (vii) −x+2, −y+1, −z+1.