4-Benzyl-3,5-dimethyl-1H-pyrazole.

In the title mol-ecule, C(12)H(14)N(2), the dihedral angle between the pyrazole and phenyl ring mean planes is 78.65 (19)°. In the crystal, mol-ecules are linked by N-H⋯N hydrogen bonds into chains along [010].

Related literature

For the pharmacological activity of pyrazole derivatives, see: Adnan & Tarek (2004 ▶); Ashraf et al. (2003 ▶). For a related structure, see: Wang & Jian (2010 ▶). For standard bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C12H14N2

M = 186.25

Monoclinic,

a = 6.2303 (6) Å

b = 5.5941 (5) Å

c = 15.1364 (15) Å

β = 97.049 (1)°

V = 523.56 (9) Å3

Z = 2

Mo Kα radiation

μ = 0.07 mm−1

T = 298 K

0.48 × 0.32 × 0.15 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.967, T max = 0.989

2666 measured reflections

1023 independent reflections

756 reflections with I > 2σ(I)

R int = 0.043

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.107

S = 0.95

1023 reflections

127 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.11 e Å−3

Δρmin = −0.13 e Å−3

Data collection: SMART (Bruker, 1997 ▶); cell refinement: SAINT (Bruker, 1997 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811045405/lh5342sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811045405/lh5342Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811045405/lh5342Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C12H14N2	F(000) = 200
Mr = 186.25	Dx = 1.181 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 648 reflections
a = 6.2303 (6) Å	θ = 2.7–20.1°
b = 5.5941 (5) Å	µ = 0.07 mm−1
c = 15.1364 (15) Å	T = 298 K
β = 97.049 (1)°	Block, colorless
V = 523.56 (9) Å3	0.48 × 0.32 × 0.15 mm
Z = 2

Bruker SMART CCD diffractometer	1023 independent reflections
Radiation source: fine-focus sealed tube	756 reflections with I > 2σ(I)
graphite	Rint = 0.043
φ and ω scans	θmax = 25.0°, θmin = 2.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −6→7
Tmin = 0.967, Tmax = 0.989	k = −6→6
2666 measured reflections	l = −16→18

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.107	H-atom parameters constrained
S = 0.95	w = 1/[σ2(Fo2) + (0.0568P)2] where P = (Fo2 + 2Fc2)/3
1023 reflections	(Δ/σ)max < 0.001
127 parameters	Δρmax = 0.11 e Å−3
1 restraint	Δρmin = −0.13 e Å−3

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.

	x	y	z	Uiso*/Ueq
N1	0.4939 (4)	0.1998 (6)	0.91543 (15)	0.0558 (7)
N2	0.6284 (4)	0.3826 (6)	0.94362 (13)	0.0536 (7)
H2	0.6092	0.4729	0.9880	0.064*
C1	0.9603 (5)	0.5915 (7)	0.91602 (19)	0.0672 (10)
H1A	0.9315	0.7234	0.8758	0.101*
H1B	1.0990	0.5241	0.9091	0.101*
H1C	0.9604	0.6464	0.9761	0.101*
C2	0.7922 (4)	0.4085 (6)	0.89629 (17)	0.0471 (7)
C3	0.7654 (4)	0.2339 (6)	0.83141 (16)	0.0451 (7)
C4	0.5795 (5)	0.1098 (6)	0.84614 (18)	0.0479 (8)
C5	0.4757 (5)	−0.0964 (8)	0.7964 (2)	0.0703 (10)
H5A	0.3904	−0.1838	0.8341	0.106*
H5B	0.5851	−0.1993	0.7779	0.106*
H5C	0.3842	−0.0398	0.7450	0.106*
C6	0.9109 (5)	0.1927 (8)	0.76133 (18)	0.0600 (9)
H6A	0.8811	0.0356	0.7356	0.072*
H6B	1.0597	0.1934	0.7891	0.072*
C7	0.8863 (5)	0.3750 (7)	0.68827 (18)	0.0548 (8)
C8	0.6936 (6)	0.4084 (9)	0.6353 (2)	0.0737 (10)
H8	0.5753	0.3144	0.6446	0.088*
C9	0.6716 (7)	0.5754 (9)	0.5699 (2)	0.0910 (14)
H9	0.5393	0.5939	0.5348	0.109*
C10	0.8423 (9)	0.7162 (9)	0.5551 (2)	0.0953 (14)
H10	0.8268	0.8309	0.5104	0.114*
C11	1.0345 (8)	0.6876 (9)	0.6063 (3)	0.0900 (14)
H11	1.1517	0.7829	0.5967	0.108*
C12	1.0566 (6)	0.5183 (8)	0.6721 (2)	0.0726 (11)
H12	1.1897	0.4998	0.7067	0.087*

	U11	U22	U33	U12	U13	U23
N1	0.0603 (15)	0.0557 (18)	0.0530 (14)	−0.0014 (16)	0.0135 (12)	0.0051 (16)
N2	0.0644 (16)	0.0562 (18)	0.0419 (12)	0.0048 (19)	0.0135 (11)	0.0001 (15)
C1	0.074 (2)	0.060 (2)	0.066 (2)	−0.012 (2)	0.0049 (17)	−0.0028 (19)
C2	0.0515 (17)	0.0453 (18)	0.0449 (14)	0.0028 (18)	0.0073 (12)	0.0069 (17)
C3	0.0527 (17)	0.0435 (19)	0.0393 (14)	0.0099 (17)	0.0063 (13)	0.0033 (15)
C4	0.0495 (17)	0.0473 (19)	0.0462 (16)	0.0033 (16)	0.0036 (14)	0.0014 (16)
C5	0.070 (2)	0.059 (2)	0.081 (2)	−0.005 (2)	0.0025 (17)	−0.007 (2)
C6	0.0623 (19)	0.064 (2)	0.0563 (17)	0.011 (2)	0.0169 (15)	−0.003 (2)
C7	0.064 (2)	0.057 (2)	0.0461 (15)	0.005 (2)	0.0173 (15)	−0.0083 (19)
C8	0.080 (2)	0.081 (3)	0.0602 (19)	−0.009 (3)	0.0101 (18)	0.005 (3)
C9	0.106 (3)	0.099 (4)	0.068 (2)	0.001 (3)	0.007 (2)	0.019 (3)
C10	0.158 (4)	0.073 (3)	0.060 (2)	−0.002 (4)	0.031 (3)	0.008 (2)
C11	0.124 (4)	0.081 (3)	0.074 (2)	−0.033 (3)	0.046 (3)	−0.016 (3)
C12	0.076 (2)	0.080 (3)	0.065 (2)	−0.012 (2)	0.0212 (19)	−0.009 (2)

N1—C4	1.332 (3)	C6—C7	1.498 (5)
N1—N2	1.357 (4)	C6—H6A	0.9700
N2—C2	1.325 (3)	C6—H6B	0.9700
N2—H2	0.8600	C7—C8	1.372 (5)
C1—C2	1.469 (4)	C7—C12	1.375 (5)
C1—H1A	0.9600	C8—C9	1.357 (5)
C1—H1B	0.9600	C8—H8	0.9300
C1—H1C	0.9600	C9—C10	1.364 (6)
C2—C3	1.381 (5)	C9—H9	0.9300
C3—C4	1.392 (4)	C10—C11	1.353 (6)
C3—C6	1.495 (3)	C10—H10	0.9300
C4—C5	1.482 (5)	C11—C12	1.370 (6)
C5—H5A	0.9600	C11—H11	0.9300
C5—H5B	0.9600	C12—H12	0.9300
C5—H5C	0.9600
C4—N1—N2	103.9 (2)	C3—C6—C7	113.7 (3)
C2—N2—N1	113.5 (2)	C3—C6—H6A	108.8
C2—N2—H2	123.2	C7—C6—H6A	108.8
N1—N2—H2	123.2	C3—C6—H6B	108.8
C2—C1—H1A	109.5	C7—C6—H6B	108.8
C2—C1—H1B	109.5	H6A—C6—H6B	107.7
H1A—C1—H1B	109.5	C8—C7—C12	117.1 (4)
C2—C1—H1C	109.5	C8—C7—C6	121.8 (3)
H1A—C1—H1C	109.5	C12—C7—C6	121.1 (3)
H1B—C1—H1C	109.5	C9—C8—C7	121.6 (4)
N2—C2—C3	105.9 (3)	C9—C8—H8	119.2
N2—C2—C1	122.9 (3)	C7—C8—H8	119.2
C3—C2—C1	131.2 (3)	C8—C9—C10	120.4 (4)
C2—C3—C4	105.6 (2)	C8—C9—H9	119.8
C2—C3—C6	125.7 (3)	C10—C9—H9	119.8
C4—C3—C6	128.7 (3)	C11—C10—C9	119.4 (4)
N1—C4—C3	111.0 (3)	C11—C10—H10	120.3
N1—C4—C5	120.1 (3)	C9—C10—H10	120.3
C3—C4—C5	128.8 (3)	C10—C11—C12	120.1 (4)
C4—C5—H5A	109.5	C10—C11—H11	120.0
C4—C5—H5B	109.5	C12—C11—H11	120.0
H5A—C5—H5B	109.5	C11—C12—C7	121.4 (4)
C4—C5—H5C	109.5	C11—C12—H12	119.3
H5A—C5—H5C	109.5	C7—C12—H12	119.3
H5B—C5—H5C	109.5
C4—N1—N2—C2	−0.6 (3)	C2—C3—C6—C7	−74.5 (4)
N1—N2—C2—C3	0.7 (3)	C4—C3—C6—C7	105.8 (4)
N1—N2—C2—C1	−178.7 (3)	C3—C6—C7—C8	−60.6 (5)
N2—C2—C3—C4	−0.5 (3)	C3—C6—C7—C12	118.7 (3)
C1—C2—C3—C4	178.8 (3)	C12—C7—C8—C9	0.0 (5)
N2—C2—C3—C6	179.8 (3)	C6—C7—C8—C9	179.3 (3)
C1—C2—C3—C6	−1.0 (5)	C7—C8—C9—C10	−0.2 (6)
N2—N1—C4—C3	0.2 (3)	C8—C9—C10—C11	0.2 (7)
N2—N1—C4—C5	−179.9 (3)	C9—C10—C11—C12	0.0 (7)
C2—C3—C4—N1	0.1 (3)	C10—C11—C12—C7	−0.3 (6)
C6—C3—C4—N1	179.9 (3)	C8—C7—C12—C11	0.2 (5)
C2—C3—C4—C5	−179.8 (3)	C6—C7—C12—C11	−179.1 (3)
C6—C3—C4—C5	0.0 (5)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···N1i	0.86	2.09	2.946 (4)	170

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯N1i	0.86	2.09	2.946 (4)	170

Symmetry code: (i) .