5-Chloro-1-phenyl-1H-tetra­zole

Abstract

The tetra­zole and phenyl rings of the title compound, C₇H₅ClN₄, form a dihedral angle 64.5°.

Related literature

For the ferroelectric properties of tetra­zole derivatives, see: Sengupta & Mukherjee (2010 ▶). For their magnetic properties, see: Grunert et al. (2004 ▶); Van Koningsbruggen et al. (2000 ▶). For their luminescent properties, see: Wang et al. (2005 ▶).

Experimental

Crystal data

• C₇H₅ClN₄

• M _r = 180.60

• Monoclinic,

• a = 7.0428 (7) Å

• b = 6.4150 (6) Å

• c = 17.5804 (18) Å

• β = 96.160 (2)°

• V = 789.69 (13) ų

• Z = 4

• Mo Kα radiation

• μ = 0.43 mm⁻¹

• T = 296 K

• 0.15 × 0.14 × 0.13 mm

Data collection

• Bruker SMART CCD area-detector diffractometer

• Absorption correction: multi-scan (SADABS; Sheldrick, 1998 ▶) T _min = 0.939, T _max = 0.947

• 3879 measured reflections

• 1404 independent reflections

• 1176 reflections with I > 2σ(I)

• R _int = 0.014

Refinement

• R[F ² > 2σ(F ²)] = 0.033

• wR(F ²) = 0.092

• S = 1.05

• 1404 reflections

• 109 parameters

• H-atom parameters constrained

• Δρ_max = 0.12 e Å⁻³

• Δρ_min = −0.26 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.

Supplementary Material

Supplementary material file. DOI: 10.1107/S1600536811021210/aa2009Isup3.cml

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

supplementary crystallographic information

Comment

The design and synthesis of new tetrazole derivatives have attracted much interest owing to their ferroecletric (Sengupta & Mukherjee, 2010), luminescent (Wang et al., 2005) and magnetic properties (Grunert et al., 2004; Van Koningsbruggen et al., 2000). The crystal structure of 5-chloro-1-phenyl-1H-tetrazole (I) is shown in Fig. 1.

Experimental

5-Chloro-1-phenyl-1H-tetrazole (I) (54.18 mg, 0.3 mmol) was stirred for 0.5 h in H₂O (5 ml) and CH₃CN (5 ml). Upon slow evaporation of the filtrate at room temperatre for two weeks, well shaped colorless crystals suitable for X-ray diffraction were obtained. Yield: 90%. Elemental analysis calcd (%) for (I): C 46.55, H 2.79, N 31.02%; found: C 46.26, H 2.68, N 31.37%.

Refinement

H atoms were introduced in their idealized positions and refined as riding with C—H 0.93 Å.

Figures

Fig. 1.

A view of (I), with displacement ellipsoids drawn at the 30% probability level. Hydrogen atoms are drawn as circles.

Crystal data

C7H5ClN4	F(000) = 368
Mr = 180.60	Dx = 1.519 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1689 reflections
a = 7.0428 (7) Å	θ = 3.0–27.2°
b = 6.4150 (6) Å	µ = 0.43 mm−1
c = 17.5804 (18) Å	T = 296 K
β = 96.160 (2)°	Block, colourless
V = 789.69 (13) Å3	0.15 × 0.14 × 0.13 mm
Z = 4

Data collection

Bruker SMART CCD area-detector diffractometer	1404 independent reflections
Radiation source: fine-focus sealed tube	1176 reflections with I > 2σ(I)
graphite	Rint = 0.014
φ and ω scans	θmax = 25.0°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1998)	h = −5→8
Tmin = 0.939, Tmax = 0.947	k = −7→7
3879 measured reflections	l = −20→20

Refinement

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)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.092	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0501P)2 + 0.1635P] where P = (Fo2 + 2Fc2)/3
1404 reflections	(Δ/σ)max < 0.001
109 parameters	Δρmax = 0.12 e Å−3
0 restraints	Δρmin = −0.26 e Å−3

Special details

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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
Cl1	0.15030 (6)	0.26017 (7)	0.03941 (3)	0.05392 (19)
N1	0.5232 (2)	0.25483 (17)	0.08796 (8)	0.0387 (3)
N2	0.4612 (3)	0.24646 (19)	−0.03563 (9)	0.0527 (4)
N3	0.6525 (3)	0.2414 (2)	−0.01533 (10)	0.0558 (4)
N4	0.6930 (2)	0.24610 (19)	0.05813 (10)	0.0504 (4)
C1	0.3852 (3)	0.2547 (2)	0.02910 (10)	0.0416 (4)
C2	0.5109 (2)	0.2662 (2)	0.16905 (9)	0.0417 (4)
C3	0.4356 (2)	0.4431 (3)	0.19789 (9)	0.0505 (4)
H3	0.3949	0.5534	0.1659	0.061*
C4	0.4216 (3)	0.4538 (4)	0.27567 (10)	0.0646 (6)
H4	0.3699	0.5716	0.2963	0.078*
C5	0.4836 (3)	0.2919 (4)	0.32218 (11)	0.0709 (7)
H5	0.4740	0.3003	0.3744	0.085*
C6	0.5600 (3)	0.1167 (4)	0.29252 (11)	0.0725 (6)
H6	0.6029	0.0080	0.3249	0.087*
C7	0.5737 (2)	0.1004 (3)	0.21435 (10)	0.0570 (5)
H7	0.6235	−0.0183	0.1936	0.068*

Atomic displacement parameters (Ų)

	U11	U22	U33	U12	U13	U23
Cl1	0.0445 (3)	0.0682 (3)	0.0478 (3)	−0.00030 (19)	−0.0010 (2)	0.00150 (18)
N1	0.0380 (7)	0.0418 (7)	0.0376 (7)	0.0000 (5)	0.0103 (6)	−0.0016 (5)
N2	0.0734 (11)	0.0471 (9)	0.0396 (8)	−0.0045 (7)	0.0160 (8)	−0.0009 (6)
N3	0.0706 (11)	0.0479 (9)	0.0542 (10)	−0.0037 (7)	0.0309 (8)	−0.0039 (6)
N4	0.0477 (8)	0.0495 (8)	0.0577 (10)	−0.0012 (6)	0.0218 (7)	−0.0035 (6)
C1	0.0509 (10)	0.0367 (8)	0.0380 (9)	−0.0018 (6)	0.0083 (8)	0.0009 (6)
C2	0.0345 (8)	0.0559 (10)	0.0350 (8)	−0.0008 (7)	0.0052 (7)	0.0007 (6)
C3	0.0512 (10)	0.0596 (11)	0.0411 (9)	0.0060 (8)	0.0069 (7)	−0.0032 (8)
C4	0.0580 (12)	0.0918 (15)	0.0448 (10)	0.0055 (10)	0.0089 (9)	−0.0151 (10)
C5	0.0493 (11)	0.128 (2)	0.0349 (10)	−0.0011 (12)	0.0031 (8)	0.0015 (11)
C6	0.0518 (12)	0.1107 (18)	0.0532 (11)	0.0097 (12)	−0.0020 (9)	0.0329 (12)
C7	0.0463 (10)	0.0684 (12)	0.0567 (11)	0.0117 (8)	0.0077 (8)	0.0134 (9)

Geometric parameters (Å, °)

Cl1—C1	1.6841 (18)	C3—C4	1.383 (2)
N1—C1	1.341 (2)	C3—H3	0.9300
N1—N4	1.357 (2)	C4—C5	1.364 (3)
N1—C2	1.439 (2)	C4—H4	0.9300
N2—C1	1.309 (2)	C5—C6	1.373 (3)
N2—N3	1.357 (3)	C5—H5	0.9300
N3—N4	1.293 (2)	C6—C7	1.392 (3)
C2—C3	1.373 (2)	C6—H6	0.9300
C2—C7	1.373 (2)	C7—H7	0.9300
C1—N1—N4	107.28 (15)	C4—C3—H3	120.7
C1—N1—C2	130.44 (14)	C5—C4—C3	120.20 (19)
N4—N1—C2	122.27 (14)	C5—C4—H4	119.9
C1—N2—N3	105.02 (16)	C3—C4—H4	119.9
N4—N3—N2	111.63 (15)	C4—C5—C6	120.57 (18)
N3—N4—N1	106.14 (16)	C4—C5—H5	119.7
N2—C1—N1	109.93 (17)	C6—C5—H5	119.7
N2—C1—Cl1	126.31 (16)	C5—C6—C7	120.52 (18)
N1—C1—Cl1	123.75 (14)	C5—C6—H6	119.7
C3—C2—C7	122.63 (16)	C7—C6—H6	119.7
C3—C2—N1	118.32 (14)	C2—C7—C6	117.56 (18)
C7—C2—N1	119.05 (14)	C2—C7—H7	121.2
C2—C3—C4	118.51 (17)	C6—C7—H7	121.2
C2—C3—H3	120.7
C1—N2—N3—N4	0.03 (16)	N4—N1—C2—C3	115.00 (16)
N2—N3—N4—N1	−0.05 (16)	C1—N1—C2—C7	116.21 (18)
C1—N1—N4—N3	0.04 (15)	N4—N1—C2—C7	−65.26 (19)
C2—N1—N4—N3	−178.79 (12)	C7—C2—C3—C4	−0.4 (3)
N3—N2—C1—N1	−0.01 (15)	N1—C2—C3—C4	179.32 (15)
N3—N2—C1—Cl1	−178.96 (11)	C2—C3—C4—C5	0.7 (3)
N4—N1—C1—N2	−0.02 (16)	C3—C4—C5—C6	−0.1 (3)
C2—N1—C1—N2	178.68 (13)	C4—C5—C6—C7	−0.7 (3)
N4—N1—C1—Cl1	178.96 (10)	C3—C2—C7—C6	−0.4 (3)
C2—N1—C1—Cl1	−2.3 (2)	N1—C2—C7—C6	179.91 (16)
C1—N1—C2—C3	−63.5 (2)	C5—C6—C7—C2	0.9 (3)