5-(4-Chloro-phen-yl)-1H-tetra-zole.

The two independent mol-ecules of the title compound, C(7)H(5)ClN(4), both lie on a twofold rotation axis that passes through the centroids of the five- and six-membered rings and the attached Cl C atom. One molecule is nearly planar [dihedral angle between rings = 0.22 (6)°], whereas the other is significantly twisted [dihedral angle = 17.38 (6)°]. In the crystal, adjacent mol-ecules are linked by N-H⋯N hydrogen bonds into a chain structure.

Related literature

For the synthesis, see: Xu et al. (2009 ▶). For a related structure, see: Luo et al. (2006 ▶).

Experimental

Crystal data

C7H5ClN4

M = 180.60

Monoclinic,

a = 9.4596 (19) Å

b = 11.437 (2) Å

c = 7.2988 (15) Å

β = 107.91 (3)°

V = 751.4 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.45 mm−1

T = 291 K

0.21 × 0.14 × 0.11 mm

Data collection

Rigaku R-AXIS RAPID diffractometer

Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.912, T max = 0.952

7237 measured reflections

1720 independent reflections

1194 reflections with I > 2σ(I)

R int = 0.038

Refinement

R[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.135

S = 1.05

1720 reflections

118 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.77 e Å−3

Δρmin = −0.24 e Å−3

Data collection: RAPID-AUTO (Rigaku, 1998 ▶); cell refinement: RAPID-AUTO; data reduction: CrystalClear (Rigaku/MSC, 2002 ▶); 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: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810003788/ng2726sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810003788/ng2726Isup2.hkl

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

C7H5ClN4	F(000) = 368
Mr = 180.60	Dx = 1.596 Mg m−3
Monoclinic, P2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yc	Cell parameters from 5352 reflections
a = 9.4596 (19) Å	θ = 3.1–27.5°
b = 11.437 (2) Å	µ = 0.45 mm−1
c = 7.2988 (15) Å	T = 291 K
β = 107.91 (3)°	Block, colorless
V = 751.4 (3) Å3	0.21 × 0.14 × 0.11 mm
Z = 4

Rigaku R-AXIS RAPID diffractometer	1720 independent reflections
Radiation source: fine-focus sealed tube	1194 reflections with I > 2σ(I)
graphite	Rint = 0.038
ω scan	θmax = 27.5°, θmin = 3.4°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −12→12
Tmin = 0.912, Tmax = 0.952	k = −14→14
7237 measured reflections	l = −9→9

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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.135	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ2(Fo2) + (0.0807P)2] where P = (Fo2 + 2Fc2)/3
1720 reflections	(Δ/σ)max < 0.001
118 parameters	Δρmax = 0.77 e Å−3
0 restraints	Δρmin = −0.24 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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	Occ. (<1)
C1	0.0000	0.7724 (3)	0.2500	0.0340 (7)
C2	0.1238 (2)	0.7123 (2)	0.3612 (3)	0.0375 (5)
H1	0.2067	0.7530	0.4358	0.045*
C3	0.1235 (2)	0.59197 (19)	0.3606 (3)	0.0331 (5)
H2	0.2068	0.5518	0.4350	0.040*
C4	0.0000	0.5293 (3)	0.2500	0.0282 (6)
C5	0.0000	0.4029 (3)	0.2500	0.0288 (6)
C6	0.5000	−0.0727 (3)	0.7500	0.0296 (6)
C7	0.3680 (2)	−0.0135 (2)	0.6704 (3)	0.0389 (5)
H4	0.2797	−0.0544	0.6188	0.047*
C8	0.3688 (2)	0.1065 (2)	0.6683 (3)	0.0354 (5)
H5	0.2809	0.1471	0.6119	0.042*
C9	0.5000	0.1681 (2)	0.7500	0.0258 (6)
C10	0.5000	0.2975 (3)	0.7500	0.0267 (6)
Cl1	0.0000	0.92391 (7)	0.2500	0.0492 (3)
Cl2	0.5000	−0.22534 (7)	0.7500	0.0464 (3)
N1	0.1109 (2)	0.33285 (16)	0.3488 (2)	0.0349 (4)
H3	0.1934	0.3493	0.4318	0.050 (15)*	0.50
N2	0.0660 (2)	0.22079 (17)	0.3089 (3)	0.0418 (5)
N3	0.3941 (2)	0.36603 (16)	0.6406 (3)	0.0349 (4)
H6	0.322 (5)	0.352 (4)	0.545 (6)	0.016 (9)*	0.50
N4	0.4364 (2)	0.47685 (17)	0.6842 (3)	0.0398 (5)

	U11	U22	U33	U12	U13	U23
C1	0.0332 (14)	0.0274 (17)	0.0377 (15)	0.000	0.0056 (12)	0.000
C2	0.0313 (10)	0.0320 (12)	0.0424 (11)	−0.0035 (8)	0.0011 (9)	−0.0024 (9)
C3	0.0270 (9)	0.0298 (12)	0.0349 (10)	0.0000 (8)	−0.0016 (8)	0.0017 (8)
C4	0.0267 (13)	0.0285 (17)	0.0270 (13)	0.000	0.0046 (11)	0.000
C5	0.0305 (13)	0.0261 (15)	0.0266 (12)	0.000	0.0038 (11)	0.000
C6	0.0365 (14)	0.0215 (15)	0.0272 (13)	0.000	0.0047 (12)	0.000
C7	0.0324 (11)	0.0310 (12)	0.0456 (12)	−0.0054 (8)	0.0006 (10)	−0.0066 (9)
C8	0.0242 (9)	0.0328 (12)	0.0408 (11)	0.0009 (8)	−0.0021 (8)	−0.0002 (9)
C9	0.0292 (13)	0.0219 (15)	0.0238 (12)	0.000	0.0044 (11)	0.000
C10	0.0248 (12)	0.0282 (16)	0.0244 (12)	0.000	0.0037 (11)	0.000
Cl1	0.0465 (5)	0.0241 (5)	0.0709 (6)	0.000	0.0090 (4)	0.000
Cl2	0.0591 (5)	0.0225 (5)	0.0503 (5)	0.000	0.0061 (4)	0.000
N1	0.0332 (8)	0.0275 (10)	0.0356 (9)	0.0027 (7)	−0.0019 (8)	0.0001 (7)
N2	0.0437 (10)	0.0245 (10)	0.0456 (10)	0.0031 (8)	−0.0036 (8)	0.0027 (8)
N3	0.0329 (9)	0.0257 (10)	0.0374 (9)	0.0008 (7)	−0.0018 (8)	0.0000 (7)
N4	0.0381 (9)	0.0259 (10)	0.0450 (10)	0.0016 (8)	−0.0027 (8)	0.0002 (8)

C1—C2	1.385 (3)	C7—C8	1.373 (3)
C1—C2i	1.385 (3)	C7—H4	0.9300
C1—Cl1	1.732 (3)	C8—C9	1.392 (2)
C2—C3	1.376 (3)	C8—H5	0.9300
C2—H1	0.9300	C9—C8ii	1.392 (2)
C3—C4	1.397 (3)	C9—C10	1.480 (4)
C3—H2	0.9300	C10—N3ii	1.328 (3)
C4—C3i	1.397 (3)	C10—N3	1.328 (3)
C4—C5	1.446 (4)	N1—N2	1.353 (3)
C5—N1i	1.340 (3)	N1—H3	0.8492
C5—N1	1.340 (3)	N2—N2i	1.280 (4)
C6—C7ii	1.382 (3)	N3—N4	1.338 (3)
C6—C7	1.382 (3)	N3—H6	0.83 (4)
C6—Cl2	1.746 (3)	N4—N4ii	1.288 (3)
C2—C1—C2i	120.5 (3)	C8—C7—H4	120.4
C2—C1—Cl1	119.77 (15)	C6—C7—H4	120.4
C2i—C1—Cl1	119.77 (15)	C7—C8—C9	120.55 (19)
C3—C2—C1	119.6 (2)	C7—C8—H5	119.7
C3—C2—H1	120.2	C9—C8—H5	119.7
C1—C2—H1	120.2	C8—C9—C8ii	119.2 (3)
C2—C3—C4	121.05 (19)	C8—C9—C10	120.38 (13)
C2—C3—H2	119.5	C8ii—C9—C10	120.38 (14)
C4—C3—H2	119.5	N3ii—C10—N3	107.6 (3)
C3—C4—C3i	118.2 (3)	N3ii—C10—C9	126.18 (13)
C3—C4—C5	120.88 (14)	N3—C10—C9	126.18 (13)
C3i—C4—C5	120.88 (14)	C5—N1—N2	107.97 (18)
N1i—C5—N1	106.6 (3)	C5—N1—H3	130.3
N1i—C5—C4	126.70 (14)	N2—N1—H3	121.5
N1—C5—C4	126.70 (14)	N2i—N2—N1	108.73 (11)
C7ii—C6—C7	121.3 (3)	C10—N3—N4	107.51 (18)
C7ii—C6—Cl2	119.34 (14)	C10—N3—H6	131 (3)
C7—C6—Cl2	119.34 (14)	N4—N3—H6	120 (3)
C8—C7—C6	119.1 (2)	N4ii—N4—N3	108.67 (11)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H3···N3	0.85 (1)	2.05 (1)	2.889 (2)	172 (1)
N3—H6···N1	0.83 (3)	2.08 (4)	2.889 (2)	165.7 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H3⋯N3	0.85 (1)	2.05 (1)	2.889 (2)	172 (1)
N3—H6⋯N1	0.83 (3)	2.08 (4)	2.889 (2)	165.7 (2)