4-{5-[(2-Bromo-benz-yl)sulfan-yl]-1H-tetra-zol-1-yl}benzoic acid.

In the title compound, C15H11BrN4O2S, the tetra-zole ring makes dihedral angles of 45.97 (10) and 75.41 (1)°, respectively, with the benzoyl and bromo-benzene rings while the dihedral angle between the benzene rings is 73.77 (1)°. In the crystal, mol-ecules are linked through O-H⋯ N and C-H⋯ O hydrogen bonds, giving infinite chains in both the [110] and [1-10] directions. These chains are further connected by C-Br⋯π and C-O⋯π inter-actions and also by π-π stacking between tetra-zole rings [centroid-centroid distance = 3.312 (1) Å], generating a three-dimensional network.

Related literature

For details of the ZINC database, see: Irwin et al. (2012 ▶). For biological properties of tetra­zoles, see: Kees et al. (1989 ▶); Nolte et al. (1998 ▶); Mafud et al. (2013 ▶).

Experimental

Crystal data

C15H11BrN4O2S

M = 391.25

Monoclinic,

a = 7.4570 (5) Å

b = 8.3500 (5) Å

c = 25.3680 (14) Å

β = 97.626 (3)°

V = 1565.59 (17) Å3

Z = 4

Mo Kα radiation

μ = 2.77 mm−1

T = 290 K

0.1 x 0.1 (radius) mm

Data collection

Nonius KappaCCD diffractometer

Absorption correction: for a cylinder mounted on the ϕ axis (modified Dwiggins, 1975 ▶) T min = 0.604, T max = 0.608

24464 measured reflections

2889 independent reflections

2388 reflections with I > 2σ(I)

R int = 0.069

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.114

S = 1.06

2889 reflections

213 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.38 e Å−3

Δρmin = −0.47 e Å−3

Data collection: COLLECT (Nonius, 1999 ▶); cell refinement: SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: DENZO (Otwinowski & Minor, 1997 ▶) and SCALEPACK; program(s) used to solve structure: SIR92 (Altomare et al., 1994 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶) and Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813014840/lr2105sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813014840/lr2105Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813014840/lr2105Isup3.cml

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

C15H11BrN4O2S	F(000) = 784
Mr = 391.25	Dx = 1.66 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3980 reflections
a = 7.4570 (5) Å	θ = 12.0–18.1°
b = 8.3500 (5) Å	µ = 2.77 mm−1
c = 25.3680 (14) Å	T = 290 K
β = 97.626 (3)°	Prism, colourless
V = 1565.59 (17) Å3	0.1 × 0.1 × 0.1 × 0.1 (radius) mm
Z = 4

Nonius KappaCCD diffractometer	2889 independent reflections
Graphite monochromator	2388 reflections with I > 2σ(I)
Detector resolution: 9 pixels mm-1	Rint = 0.069
CCD scans	θmax = 25.7°, θmin = 2.9°
Absorption correction: for a cylinder mounted on the φ axis (Dwiggins, 1975)	h = −9→9
Tmin = 0.604, Tmax = 0.608	k = −10→10
24464 measured reflections	l = −30→30

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.114	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ2(Fo2) + (0.0623P)2 + 0.5855P] where P = (Fo2 + 2Fc2)/3
2889 reflections	(Δ/σ)max < 0.001
213 parameters	Δρmax = 0.38 e Å−3
0 restraints	Δρmin = −0.47 e Å−3

Experimental. Absorption correction: interpolation using Int.Tab. Vol. C (1992) p. 523,Tab. 6.3.3.3 for values of muR in the range 0-2.5, and Int.Tab. Vol.II (1959) p.302; Table 5.3.6 B for muR in the range 2.6-10.0. The interpolation procedure of (Dwiggins, 1975) is used with some modification

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
Br1	0.16110 (5)	−0.03469 (5)	0.285194 (14)	0.07850 (19)
S1	0.11800 (10)	0.09831 (9)	0.14388 (3)	0.0586 (2)
O1	−0.4811 (3)	0.7429 (2)	0.08768 (9)	0.0684 (6)
O2	−0.7294 (3)	0.5931 (3)	0.06893 (9)	0.0644 (6)
H1	−0.769 (6)	0.671 (5)	0.0724 (17)	0.097*
N1	−0.1430 (3)	0.0490 (2)	0.05969 (8)	0.0424 (5)
N2	−0.1946 (3)	−0.0608 (2)	0.02100 (9)	0.0482 (5)
N3	−0.0817 (3)	−0.1770 (3)	0.02891 (9)	0.0514 (5)
N4	0.0451 (3)	−0.1480 (2)	0.07213 (8)	0.0484 (5)
C1	−0.5529 (4)	0.6156 (3)	0.07638 (10)	0.0506 (6)
C2	−0.4489 (3)	0.4647 (3)	0.07046 (10)	0.0462 (6)
C3	−0.5338 (3)	0.3184 (3)	0.06132 (11)	0.0515 (6)
H3	−0.6594	0.3124	0.0577	0.062*
C4	−0.4328 (3)	0.1809 (3)	0.05749 (10)	0.0496 (6)
H4	−0.4891	0.0819	0.0515	0.059*
C5	−0.2460 (3)	0.1937 (3)	0.06285 (9)	0.0421 (5)
C6	−0.1586 (3)	0.3385 (3)	0.07012 (11)	0.0495 (6)
H6	−0.0334	0.3446	0.0722	0.059*
C7	−0.2614 (4)	0.4750 (3)	0.07421 (11)	0.0507 (6)
H7	−0.2048	0.5741	0.0795	0.061*
C8	0.0051 (3)	−0.0061 (3)	0.09069 (10)	0.0442 (5)
C9	0.2832 (4)	−0.0542 (4)	0.16947 (12)	0.0618 (8)
H9A	0.2221	−0.1435	0.1838	0.074*
H9B	0.3459	−0.0938	0.141	0.074*
C10	0.4163 (4)	0.0194 (3)	0.21228 (11)	0.0568 (7)
C11	0.3845 (4)	0.0329 (3)	0.26468 (11)	0.0567 (7)
C12	0.5133 (4)	0.0977 (4)	0.30333 (13)	0.0699 (8)
H12	0.4902	0.1031	0.3384	0.084*
C13	0.6728 (5)	0.1533 (5)	0.29027 (15)	0.0862 (11)
H13	0.7582	0.197	0.3164	0.103*
C14	0.7079 (5)	0.1450 (6)	0.23877 (17)	0.0932 (12)
H14	0.8159	0.1852	0.2297	0.112*
C15	0.5817 (4)	0.0764 (5)	0.20012 (14)	0.0781 (10)
H15	0.6081	0.0684	0.1654	0.094*

	U11	U22	U33	U12	U13	U23
Br1	0.0729 (3)	0.0918 (3)	0.0707 (3)	−0.00307 (17)	0.00932 (18)	0.00600 (16)
S1	0.0576 (4)	0.0567 (4)	0.0563 (4)	0.0182 (3)	−0.0120 (3)	−0.0109 (3)
O1	0.0681 (12)	0.0486 (11)	0.0884 (15)	0.0129 (10)	0.0105 (10)	−0.0114 (10)
O2	0.0531 (12)	0.0549 (12)	0.0823 (14)	0.0223 (9)	−0.0014 (10)	−0.0076 (10)
N1	0.0388 (10)	0.0404 (11)	0.0466 (11)	0.0060 (8)	0.0005 (8)	−0.0039 (8)
N2	0.0435 (11)	0.0446 (11)	0.0550 (12)	0.0048 (9)	0.0011 (9)	−0.0070 (9)
N3	0.0468 (11)	0.0477 (12)	0.0583 (13)	0.0048 (9)	0.0018 (9)	−0.0063 (10)
N4	0.0445 (11)	0.0464 (12)	0.0532 (12)	0.0101 (9)	0.0027 (9)	−0.0019 (9)
C1	0.0530 (15)	0.0498 (16)	0.0480 (14)	0.0154 (12)	0.0030 (11)	−0.0014 (11)
C2	0.0472 (14)	0.0459 (14)	0.0442 (13)	0.0136 (11)	0.0013 (10)	0.0011 (10)
C3	0.0391 (12)	0.0516 (14)	0.0623 (15)	0.0094 (11)	0.0007 (11)	−0.0028 (12)
C4	0.0414 (13)	0.0442 (13)	0.0610 (15)	0.0043 (10)	−0.0010 (11)	−0.0028 (11)
C5	0.0409 (12)	0.0413 (12)	0.0429 (12)	0.0101 (10)	0.0012 (9)	−0.0009 (9)
C6	0.0391 (12)	0.0458 (14)	0.0624 (15)	0.0063 (10)	0.0026 (11)	−0.0007 (11)
C7	0.0500 (14)	0.0413 (13)	0.0589 (15)	0.0015 (11)	0.0009 (12)	−0.0023 (11)
C8	0.0406 (12)	0.0457 (13)	0.0456 (13)	0.0090 (10)	0.0037 (10)	0.0001 (10)
C9	0.0615 (17)	0.0648 (18)	0.0545 (16)	0.0235 (14)	−0.0098 (13)	−0.0083 (13)
C10	0.0516 (16)	0.0634 (17)	0.0519 (15)	0.0204 (13)	−0.0066 (12)	−0.0011 (12)
C11	0.0564 (16)	0.0570 (16)	0.0538 (16)	0.0134 (12)	−0.0038 (12)	0.0022 (12)
C12	0.0649 (19)	0.080 (2)	0.0589 (17)	0.0110 (16)	−0.0149 (14)	−0.0054 (15)
C13	0.066 (2)	0.105 (3)	0.079 (2)	−0.0006 (19)	−0.0213 (18)	−0.0040 (19)
C14	0.0483 (18)	0.129 (3)	0.098 (3)	0.0027 (19)	−0.0050 (17)	0.013 (2)
C15	0.0581 (18)	0.113 (3)	0.0615 (19)	0.0226 (19)	0.0036 (15)	0.0099 (18)

Br1—C11	1.896 (3)	C4—H4	0.93
S1—C8	1.728 (3)	C5—C6	1.374 (4)
S1—C9	1.830 (3)	C6—C7	1.386 (3)
O1—C1	1.208 (3)	C6—H6	0.93
O2—C1	1.318 (3)	C7—H7	0.93
O2—H1	0.72 (4)	C9—C10	1.502 (4)
N1—C8	1.349 (3)	C9—H9A	0.97
N1—N2	1.361 (3)	C9—H9B	0.97
N1—C5	1.440 (3)	C10—C11	1.386 (4)
N2—N3	1.283 (3)	C10—C15	1.394 (5)
N3—N4	1.371 (3)	C11—C12	1.388 (4)
N4—C8	1.324 (3)	C12—C13	1.358 (5)
C1—C2	1.498 (3)	C12—H12	0.93
C2—C3	1.381 (4)	C13—C14	1.368 (6)
C2—C7	1.392 (4)	C13—H13	0.93
C3—C4	1.384 (4)	C14—C15	1.389 (5)
C3—H3	0.93	C14—H14	0.93
C4—C5	1.386 (3)	C15—H15	0.93
C8—S1—C9	99.29 (12)	C2—C7—H7	119.9
C1—O2—H1	106 (4)	N4—C8—N1	107.7 (2)
C8—N1—N2	108.81 (18)	N4—C8—S1	128.29 (19)
C8—N1—C5	130.9 (2)	N1—C8—S1	124.04 (18)
N2—N1—C5	120.24 (19)	C10—C9—S1	108.74 (19)
N3—N2—N1	106.25 (19)	C10—C9—H9A	109.9
N2—N3—N4	111.12 (19)	S1—C9—H9A	109.9
C8—N4—N3	106.15 (19)	C10—C9—H9B	109.9
O1—C1—O2	124.2 (2)	S1—C9—H9B	109.9
O1—C1—C2	123.1 (2)	H9A—C9—H9B	108.3
O2—C1—C2	112.7 (2)	C11—C10—C15	117.0 (3)
C3—C2—C7	120.1 (2)	C11—C10—C9	123.1 (3)
C3—C2—C1	121.9 (2)	C15—C10—C9	119.9 (3)
C7—C2—C1	118.0 (2)	C10—C11—C12	121.3 (3)
C2—C3—C4	120.3 (2)	C10—C11—Br1	120.5 (2)
C2—C3—H3	119.9	C12—C11—Br1	118.2 (2)
C4—C3—H3	119.9	C13—C12—C11	120.5 (3)
C3—C4—C5	118.6 (2)	C13—C12—H12	119.8
C3—C4—H4	120.7	C11—C12—H12	119.8
C5—C4—H4	120.7	C12—C13—C14	120.0 (3)
C6—C5—C4	122.3 (2)	C12—C13—H13	120
C6—C5—N1	119.9 (2)	C14—C13—H13	120
C4—C5—N1	117.8 (2)	C13—C14—C15	119.9 (4)
C5—C6—C7	118.5 (2)	C13—C14—H14	120.1
C5—C6—H6	120.8	C15—C14—H14	120.1
C7—C6—H6	120.8	C14—C15—C10	121.4 (3)
C6—C7—C2	120.3 (2)	C14—C15—H15	119.3
C6—C7—H7	119.9	C10—C15—H15	119.3

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9B···O1i	0.97	2.41	3.351 (4)	163
O2—H1···N4ii	0.73 (4)	2.05 (4)	2.746 (3)	161 (5)
C1—O1···Cg1iii	1.21 (1)	3.62 (1)	4.534 (1)	133 (2)
C11—Br1···Cg2iv	1.90 (1)	3.58 (1)	4.895 (2)	124 (1)

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the N1–N4/C8 tetra­zole ring and the C10–C15 benzene ring, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C9—H9B⋯O1i	0.97	2.41	3.351 (4)	163
O2—H1⋯N4ii	0.73 (4)	2.05 (4)	2.746 (3)	161 (5)
C1—O1⋯Cg1iii	1.21 (1)	3.62 (1)	4.534 (1)	133 (2)
C11—Br1⋯Cg2iv	1.90 (1)	3.58 (1)	4.895 (2)	124 (1)

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .