1,4-Bis[(1H-pyrazol-1-yl)meth-yl]benzene.

In the title compound, C(14)H(14)N(4), the center of the phenyl-ene group is a crystallographic center of inversion. The compound is composed of three aromatic rings displaying a Z-like conformation. The dihedral angle between the pyrazole rings and the central phenyl ring is 83.84 (9)°.

Related literature

For background and coordination compounds with related ligands, see: Chang et al. (1993 ▶); Hou et al. (2010 ▶); Liu et al. (2011 ▶). For the crystal structure of the title compound with two solvent water mol­ecules, see: Shi et al. (2009 ▶).

Experimental

Crystal data

C14H14N4

M = 238.29

Monoclinic,

a = 5.6088 (8) Å

b = 6.8183 (10) Å

c = 16.526 (3) Å

β = 97.900 (15)°

V = 626.01 (17) Å3

Z = 2

Mo Kα radiation

μ = 0.08 mm−1

T = 295 K

0.20 × 0.20 × 0.19 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.956, T max = 0.996

2464 measured reflections

1109 independent reflections

580 reflections with I > 2σ(I)

R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.033

wR(F 2) = 0.064

S = 0.80

1109 reflections

83 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.10 e Å−3

Δρmin = −0.11 e Å−3

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT (Bruker, 1998 ▶); 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) I, global. DOI: 10.1107/S1600536811022537/im2296sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811022537/im2296Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811022537/im2296Isup3.cml

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

C14H14N4	F(000) = 252
Mr = 238.29	Dx = 1.264 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1865 reflections
a = 5.6088 (8) Å	θ = 5.3–24.1°
b = 6.8183 (10) Å	µ = 0.08 mm−1
c = 16.526 (3) Å	T = 295 K
β = 97.900 (15)°	Block, colourless
V = 626.01 (17) Å3	0.20 × 0.20 × 0.19 mm
Z = 2

Bruker SMART CCD area-detector diffractometer	1109 independent reflections
Radiation source: fine–focus sealed tube	580 reflections with I > 2σ(I)
graphite	Rint = 0.033
φ and ω scans	θmax = 25.0°, θmin = 3.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −6→6
Tmin = 0.956, Tmax = 0.996	k = −6→8
2464 measured reflections	l = −19→19

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.033	H-atom parameters constrained
wR(F2) = 0.064	w = 1/[σ2(Fo2) + (0.0265P)2] where P = (Fo2 + 2Fc2)/3
S = 0.80	(Δ/σ)max < 0.001
1109 reflections	Δρmax = 0.10 e Å−3
83 parameters	Δρmin = −0.11 e Å−3
1 restraint	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.043 (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
N2	0.3304 (2)	0.6599 (2)	0.19489 (8)	0.0484 (4)
N1	0.1491 (2)	0.76019 (19)	0.15110 (8)	0.0450 (4)
C2	0.3728 (3)	0.8298 (3)	0.00568 (11)	0.0536 (5)
H2B	0.2880	0.7135	0.0088	0.064*
C7	0.2330 (3)	0.4880 (3)	0.20879 (10)	0.0502 (5)
H7A	0.3157	0.3862	0.2378	0.060*
C1	0.5185 (3)	0.8528 (2)	−0.05491 (11)	0.0525 (5)
H1A	0.5294	0.7517	−0.0920	0.063*
C3	0.3522 (3)	0.9770 (3)	0.06120 (10)	0.0436 (4)
C6	−0.0531 (3)	0.6553 (3)	0.13893 (11)	0.0555 (5)
H6A	−0.1998	0.6959	0.1108	0.067*
C4	0.1899 (3)	0.9606 (2)	0.12664 (11)	0.0562 (5)
H4A	0.2606	1.0340	0.1742	0.067*
H4B	0.0360	1.0203	0.1068	0.067*
C5	−0.0058 (3)	0.4783 (3)	0.17507 (12)	0.0588 (5)
H5A	−0.1111	0.3735	0.1767	0.071*

	U11	U22	U33	U12	U13	U23
N2	0.0428 (8)	0.0432 (10)	0.0573 (10)	0.0048 (8)	0.0001 (7)	0.0053 (8)
N1	0.0420 (8)	0.0448 (9)	0.0484 (9)	0.0056 (8)	0.0074 (7)	0.0057 (8)
C2	0.0598 (11)	0.0468 (12)	0.0558 (12)	−0.0024 (9)	0.0134 (10)	0.0014 (11)
C7	0.0593 (13)	0.0408 (12)	0.0504 (12)	0.0055 (10)	0.0072 (10)	0.0036 (10)
C1	0.0626 (11)	0.0460 (12)	0.0490 (12)	0.0036 (10)	0.0076 (10)	−0.0051 (10)
C3	0.0454 (10)	0.0443 (11)	0.0413 (11)	0.0087 (9)	0.0067 (8)	0.0027 (10)
C6	0.0352 (10)	0.0744 (15)	0.0559 (12)	0.0007 (11)	0.0025 (8)	−0.0021 (12)
C4	0.0635 (11)	0.0458 (12)	0.0614 (13)	0.0138 (9)	0.0165 (10)	0.0119 (10)
C5	0.0551 (13)	0.0566 (14)	0.0653 (13)	−0.0144 (10)	0.0100 (11)	−0.0042 (12)

N2—C7	1.3264 (19)	C1—C3i	1.380 (2)
N2—N1	1.3504 (16)	C1—H1A	0.9300
N1—C6	1.3324 (18)	C3—C1i	1.380 (2)
N1—C4	1.4518 (19)	C3—C4	1.511 (2)
C2—C3	1.375 (2)	C6—C5	1.356 (2)
C2—C1	1.386 (2)	C6—H6A	0.9300
C2—H2B	0.9300	C4—H4A	0.9700
C7—C5	1.380 (2)	C4—H4B	0.9700
C7—H7A	0.9300	C5—H5A	0.9300
C7—N2—N1	104.04 (12)	C2—C3—C4	122.52 (16)
N2—N1—C6	111.81 (13)	C1i—C3—C4	119.39 (16)
N2—N1—C4	119.33 (14)	N1—C6—C5	107.47 (15)
C6—N1—C4	128.81 (16)	N1—C6—H6A	126.3
C3—C2—C1	120.76 (16)	C5—C6—H6A	126.3
C3—C2—H2B	119.6	N1—C4—C3	113.74 (14)
C1—C2—H2B	119.6	N1—C4—H4A	108.8
N2—C7—C5	111.86 (16)	C3—C4—H4A	108.8
N2—C7—H7A	124.1	N1—C4—H4B	108.8
C5—C7—H7A	124.1	C3—C4—H4B	108.8
C3i—C1—C2	121.18 (16)	H4A—C4—H4B	107.7
C3i—C1—H1A	119.4	C6—C5—C7	104.82 (16)
C2—C1—H1A	119.4	C6—C5—H5A	127.6
C2—C3—C1i	118.07 (15)	C7—C5—H5A	127.6