4-[(1H-Benzotriazol-1-yl)meth­yl]benzo­nitrile

In the mol­ecule of the title compound, C₁₄H₁₀N₄, which was prepared by reaction of benzotriazole with 4-(bromo­meth­yl)benzonitrile in alkaline solution, the dihedral angle between the benzotriazole and benzene ring systems is 69.03 (6)°.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.067
• wR factor = 0.182
• Data-to-parameter ratio = 16.7

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT180_ALERT_3_C Check Cell Rounding: # of Values Ending with 0 =          3
PLAT230_ALERT_2_C Hirshfeld Test Diff for    N1     -   C6      ..       6.94 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    N3     -   C5      ..       6.27 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C1     -   C2      ..       5.81 su
PLAT371_ALERT_2_C Long   C(sp2)-C(sp1) Bond  C11    -   C14    ...       1.45 Ang.

Alert level G
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   6 ALERT level C = Check and explain
   2 ALERT level G = General alerts; check

   3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   4 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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S1. Comment

Benzotriazole and its derivatives comprise an important class of corrosion inhibitors, typically used as trace additives in industrial chemical mixtures, such as coolants, cutting fluids and hydraulic fluid (Pillard et al., 2001). These derivatives are also used as inhibitors of Acanthamoeba castellanii (Kopanska et al., 2004) and are responsible for toxicity to bacteria (Gruden et al., 2001). In this paper the crystal structure of the title compound is reported.

In the title compound, bond lengths and angles observed in the benzotriazole ring system are comparable with those reported in other benzotriazole compounds (Selvanayagam et al., 2002). The dihedral angle between benzotriazole and benzene rings is 69.03 (6)°. The crystal structure is stabilized only by van der Waals contacts.

Related literature

For the application of benzotriazole compounds in industry, see: Pillard et al. (2001); Kopanska et al. (2004); Gruden et al. (2001). For the structure of a related compound, see: Selvanayagam et al. (2002).

S2. Experimental

A mixture of benzotriazole (0.01 mol) and KOH (0.56 g) in methanol (20 ml) was stirred for 10 min. 4-(Bromomethyl)benzonitrile (0.01 mol) was then added and the solution refluxed for 24 h. After completion of the reaction, the reaction mixture was evaporated under vacuum. Yellow crystals of the title compound suitable for X-ray diffraction were obtained by slow evaporation of an ethanol solution after 3 days.

S3. Refinement

All H atoms were calculated geometrically and were refined using the riding-model approximation, with C—H =0.93-0.87 Å and with U_iso(H) = 1.2U_eq (C).

Computing details

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear (Rigaku, 2005); data reduction: CrystalClear (Rigaku, 2005); 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 (Sheldrick, 2008).

Figures

Fig. 1. The molecular structure of the title compound with the atom-numbering scheme. Displacement ellipsoids were drawn at the 30% probability level.

4-[(1H-Benzotriazol-1-yl)methyl]benzonitrile

Crystal data

C14H10N4	F(000) = 488
Mr = 234.26	Dx = 1.304 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2264 reflections
a = 8.1912 (13) Å	θ = 3.0–27.4°
b = 19.0520 (9) Å	µ = 0.08 mm^−1
c = 8.6610 (6) Å	T = 293 K
β = 118.039 (1)°	Block, yellow
V = 1193.0 (2) Å^3	0.50 × 0.40 × 0.40 mm
Z = 4

Data collection

Rigaku Mercury2 diffractometer	2715 independent reflections
Radiation source: fine-focus sealed tube	1903 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.047
Detector resolution: 13.6612 pixels mm^-1	θmax = 27.5°, θmin = 3.0°
CCD Profile fitting scans	h = −10→10
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −24→24
Tmin = 0.960, Tmax = 0.969	l = −11→11
11866 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.067	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.182	H-atom parameters constrained
S = 1.09	w = 1/[σ^2(Fo^2) + (0.0763P)^2 + 0.2728P] where P = (Fo^2 + 2Fc^2)/3
2715 reflections	(Δ/σ)max = 0.002
163 parameters	Δρmax = 0.34 e Å^−3
0 restraints	Δρmin = −0.17 e Å^−3

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C1	0.7006 (4)	0.10232 (14)	0.9067 (4)	0.0662 (7)
H1A	0.6891	0.1496	0.8769	0.079*
C2	0.8443 (4)	0.07658 (15)	1.0621 (4)	0.0714 (7)
H2B	0.9320	0.1081	1.1380	0.086*
C3	0.8630 (4)	0.00549 (15)	1.1096 (4)	0.0706 (7)
C4	0.7387 (4)	−0.04391 (14)	1.0033 (4)	0.0674 (7)
H4A	0.7493	−0.0911	1.0344	0.081*
C5	0.5915 (3)	−0.01855 (12)	0.8418 (3)	0.0554 (6)
C6	0.5771 (3)	0.05233 (12)	0.8006 (3)	0.0546 (6)
C7	0.3403 (4)	0.11817 (13)	0.5272 (3)	0.0631 (6)
H7A	0.2790	0.1033	0.4058	0.076*
H7B	0.4372	0.1510	0.5420	0.076*
C8	0.2010 (3)	0.15545 (12)	0.5681 (3)	0.0513 (5)
C9	0.2298 (3)	0.22412 (12)	0.6302 (3)	0.0626 (6)
H9A	0.3379	0.2474	0.6504	0.075*
C10	0.0989 (3)	0.25833 (13)	0.6624 (3)	0.0616 (6)
H10A	0.1182	0.3044	0.7026	0.074*
C11	−0.0614 (3)	0.22289 (11)	0.6339 (3)	0.0515 (5)
C12	−0.0901 (3)	0.15394 (12)	0.5744 (3)	0.0583 (6)
H12A	−0.1967	0.1302	0.5566	0.070*
C13	0.0408 (3)	0.12081 (12)	0.5417 (3)	0.0574 (6)
H13A	0.0212	0.0747	0.5015	0.069*
C14	−0.2037 (4)	0.25735 (12)	0.6617 (3)	0.0621 (6)
N1	0.4254 (3)	0.05596 (10)	0.6402 (3)	0.0574 (5)
N2	0.3499 (3)	−0.00893 (11)	0.5862 (3)	0.0684 (6)
N3	0.4492 (3)	−0.05515 (11)	0.7082 (3)	0.0688 (6)
N4	−0.3207 (3)	0.28251 (13)	0.6795 (4)	0.0841 (8)
H3B	0.9617	−0.0085	1.2151	0.101*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0730 (16)	0.0558 (14)	0.0776 (18)	−0.0081 (12)	0.0417 (14)	−0.0063 (12)
C2	0.0659 (16)	0.0753 (18)	0.0646 (17)	−0.0119 (13)	0.0238 (13)	−0.0063 (13)
C3	0.0653 (16)	0.0776 (18)	0.0631 (16)	−0.0004 (13)	0.0253 (13)	−0.0002 (13)
C4	0.0726 (17)	0.0598 (15)	0.0774 (18)	0.0070 (12)	0.0417 (15)	0.0072 (13)
C5	0.0539 (13)	0.0533 (13)	0.0677 (15)	−0.0040 (10)	0.0358 (12)	−0.0103 (11)
C6	0.0604 (14)	0.0511 (12)	0.0641 (14)	0.0022 (10)	0.0390 (12)	−0.0023 (10)
C7	0.0645 (15)	0.0679 (15)	0.0641 (15)	0.0104 (12)	0.0361 (12)	0.0075 (12)
C8	0.0492 (12)	0.0554 (13)	0.0497 (12)	0.0039 (9)	0.0235 (10)	0.0039 (10)
C9	0.0508 (13)	0.0606 (15)	0.0791 (17)	−0.0085 (10)	0.0327 (12)	−0.0035 (12)
C10	0.0604 (14)	0.0509 (13)	0.0748 (16)	−0.0079 (11)	0.0328 (12)	−0.0098 (11)
C11	0.0509 (12)	0.0520 (12)	0.0526 (13)	0.0003 (9)	0.0252 (10)	−0.0016 (10)
C12	0.0527 (13)	0.0531 (13)	0.0713 (15)	−0.0084 (10)	0.0310 (12)	−0.0083 (11)
C13	0.0583 (14)	0.0478 (12)	0.0672 (15)	−0.0029 (10)	0.0303 (12)	−0.0084 (10)
C14	0.0659 (15)	0.0530 (13)	0.0762 (16)	−0.0044 (11)	0.0408 (13)	−0.0065 (12)
N1	0.0533 (11)	0.0651 (12)	0.0564 (12)	0.0047 (9)	0.0279 (9)	−0.0029 (9)
N2	0.0658 (13)	0.0603 (13)	0.0782 (15)	0.0012 (10)	0.0330 (11)	−0.0047 (11)
N3	0.0681 (13)	0.0547 (12)	0.0851 (15)	−0.0019 (10)	0.0373 (12)	−0.0069 (11)
N4	0.0786 (16)	0.0733 (15)	0.119 (2)	−0.0010 (12)	0.0622 (16)	−0.0153 (14)

Geometric parameters (Å, º)

C1—C6	1.379 (3)	C7—H7B	0.9700
C1—C2	1.396 (4)	C8—C13	1.388 (3)
C1—H1A	0.9301	C8—C9	1.392 (3)
C2—C3	1.403 (4)	C9—C10	1.391 (3)
C2—H2B	0.9300	C9—H9A	0.9299
C3—C4	1.374 (4)	C10—C11	1.391 (3)
C3—H3B	0.9299	C10—H10A	0.9300
C4—C5	1.435 (4)	C11—C12	1.390 (3)
C4—H4A	0.9300	C11—C14	1.453 (3)
C5—N3	1.384 (3)	C12—C13	1.383 (3)
C5—C6	1.387 (3)	C12—H12A	0.9299
C6—N1	1.362 (3)	C13—H13A	0.9300
C7—N1	1.486 (3)	C14—N4	1.145 (3)
C7—C8	1.521 (3)	N1—N2	1.363 (3)
C7—H7A	0.9700	N2—N3	1.321 (3)
C6—C1—C2	114.9 (2)	C13—C8—C9	119.1 (2)
C6—C1—H1A	122.5	C13—C8—C7	119.6 (2)
C2—C1—H1A	122.5	C9—C8—C7	121.3 (2)
C1—C2—C3	123.2 (2)	C10—C9—C8	120.7 (2)
C1—C2—H2B	118.4	C10—C9—H9A	119.6
C3—C2—H2B	118.4	C8—C9—H9A	119.6
C4—C3—C2	121.4 (2)	C11—C10—C9	119.3 (2)
C4—C3—H3B	119.4	C11—C10—H10A	120.4
C2—C3—H3B	119.3	C9—C10—H10A	120.4
C3—C4—C5	116.2 (2)	C12—C11—C10	120.4 (2)
C3—C4—H4A	121.9	C12—C11—C14	118.6 (2)
C5—C4—H4A	121.9	C10—C11—C14	121.0 (2)
N3—C5—C6	109.8 (2)	C13—C12—C11	119.7 (2)
N3—C5—C4	129.6 (2)	C13—C12—H12A	120.2
C6—C5—C4	120.6 (2)	C11—C12—H12A	120.2
N1—C6—C1	132.6 (2)	C12—C13—C8	120.8 (2)
N1—C6—C5	103.8 (2)	C12—C13—H13A	119.6
C1—C6—C5	123.6 (2)	C8—C13—H13A	119.6
N1—C7—C8	112.97 (18)	N4—C14—C11	177.3 (3)
N1—C7—H7A	109.0	C6—N1—N2	110.69 (19)
C8—C7—H7A	109.0	C6—N1—C7	129.3 (2)
N1—C7—H7B	109.0	N2—N1—C7	120.0 (2)
C8—C7—H7B	109.0	N3—N2—N1	108.7 (2)
H7A—C7—H7B	107.8	N2—N3—C5	107.0 (2)