3-(1H-Benzotriazol-1-yl)-2-bromo-1-o-tolyl­propan-1-one

In the mol­ecule of the title compound, C₁₆H₁₄BrN₃O, the benzotriazole ring system makes a dihedral angle of 62.1 (1)° with the benzene ring of the tolyl group. Weak π–π stacking inter­actions are observed between the triazole rings of inversion-related molecules, with a centroid–centroid distance of 3.726 (1) Å.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.035
• wR factor = 0.090
• Data-to-parameter ratio = 15.2

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.98

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
PLAT793_ALERT_1_G Check the Absolute Configuration of C8     = ...          R

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

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

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S1. Comment

We have recently reported the crystal structure of 2-(1H-1,2,3-benzotriazol-1-yl)-1-benzoylethyl 2-chlorobenzoate (Wan et al., 2006). As part of our ongoing studies on triazole derivatives, the title compound was synthesized and its structure is reported here.

In the molecule of the title compound, the bond lengths and angles are within normal ranges (Allen et al., 1987), and are comparable with those in the related structure (Wan et al., 2006). The benzotriazole ring system is essentially planar, with a dihedral angle of 0.8 (1)° between the triazole (N1—N3/C10/C11) and benzene (C10—C15) rings. The molecule as a whole is non-planar. The dihedral angle between the benzotriazole system (N1—N3/C10—C15) and the benzene ring (C1—C6) is 62.1 (1)°.

The crystal structure is stabilized by weak π-π stacking interactions between the triazole rings of the molecules at (x, y, z) and (1 - x, -y, 1 - z), with a centroid-centroid distance of 3.726 (1) Å.

Related literature

For a related structure, see: Wan et al. (2006). For bond-length data, see: Allen et al. (1987).

S2. Experimental

The title compound was prepared according to the literature method of Wan et al. (2006). Single crystals suitable for X-ray diffraction were obtained by slow evaporation of an ethyl acetate solution at room temperature over a period of 5 d.

S3. Refinement

All H atoms were located in difference Fourier maps and constrained to ride on their parent atoms, with C—H = 0.93–0.98 Å and U_iso(H) = 1.2 U_eq(C) or 1.5 U_eq(C_methyl).

Computing details

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL (Sheldrick, 1997b), PARST (Nardelli, 1995) and PLATON (Spek, 2003).

Figures

	Fig. 1. The molecular structure of the title compound, showing 50% probability displacement ellipsoids and the atom numbering scheme.
	Fig. 2. The crystal packing of the title compound, viewed down the c axis.

3-(1H-Benzotriazol-1-yl)-2-bromo-1-o-tolylpropan-1-one

Crystal data

C16H14BrN3O	F(000) = 696
Mr = 344.21	Dx = 1.547 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2872 reflections
a = 7.3996 (6) Å	θ = 2.7–24.1°
b = 13.1784 (11) Å	µ = 2.78 mm^−1
c = 15.4245 (13) Å	T = 293 K
β = 100.664 (1)°	Column, colourless
V = 1478.1 (2) Å^3	0.31 × 0.17 × 0.12 mm
Z = 4

Data collection

Siemens SMART 1000 CCD area-detector diffractometer	2900 independent reflections
Radiation source: fine-focus sealed tube	2281 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.018
Detector resolution: 8.33 pixels mm^-1	θmax = 26.0°, θmin = 2.1°
ω scans	h = −7→9
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −10→16
Tmin = 0.479, Tmax = 0.731	l = −19→19
8136 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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.090	H-atom parameters constrained
S = 1.01	w = 1/[σ^2(Fo^2) + (0.0463P)^2 + 0.5426P] where P = (Fo^2 + 2Fc^2)/3
2900 reflections	(Δ/σ)max = 0.001
191 parameters	Δρmax = 0.40 e Å^−3
0 restraints	Δρmin = −0.45 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
Br1	0.62383 (5)	0.35726 (2)	0.51118 (2)	0.07057 (15)
O1	0.1695 (3)	0.29617 (17)	0.50821 (11)	0.0638 (5)
N1	0.3281 (3)	0.09442 (15)	0.43516 (12)	0.0420 (5)
N2	0.3079 (3)	0.05452 (17)	0.51348 (13)	0.0509 (5)
N3	0.2174 (3)	−0.03102 (17)	0.49977 (14)	0.0530 (5)
C1	0.2527 (3)	0.37181 (18)	0.69145 (16)	0.0442 (6)
C2	0.2812 (4)	0.3790 (2)	0.78361 (17)	0.0527 (7)
H2	0.2321	0.4340	0.8090	0.063*
C3	0.3792 (4)	0.3074 (2)	0.83770 (16)	0.0546 (7)
H3	0.3943	0.3140	0.8986	0.066*
C4	0.4548 (4)	0.2263 (2)	0.80183 (16)	0.0509 (6)
H4	0.5202	0.1773	0.8382	0.061*
C5	0.4333 (3)	0.21767 (19)	0.71118 (15)	0.0461 (6)
H5	0.4868	0.1633	0.6870	0.055*
C6	0.3330 (3)	0.28894 (17)	0.65560 (14)	0.0385 (5)
C7	0.3106 (3)	0.27566 (18)	0.55829 (15)	0.0413 (5)
C8	0.4743 (3)	0.23722 (18)	0.52122 (14)	0.0432 (5)
H8	0.5447	0.1887	0.5623	0.052*
C9	0.4245 (3)	0.18998 (19)	0.43053 (15)	0.0451 (6)
H9A	0.3468	0.2362	0.3912	0.054*
H9B	0.5353	0.1781	0.4069	0.054*
C10	0.2508 (3)	0.03255 (17)	0.36834 (15)	0.0409 (5)
C11	0.1782 (3)	−0.04722 (18)	0.40969 (16)	0.0460 (6)
C12	0.0827 (4)	−0.1259 (2)	0.3607 (2)	0.0582 (7)
H12	0.0329	−0.1795	0.3878	0.070*
C13	0.0659 (4)	−0.1206 (2)	0.2715 (2)	0.0654 (8)
H13	0.0025	−0.1718	0.2370	0.078*
C14	0.1407 (4)	−0.0407 (2)	0.22958 (19)	0.0623 (7)
H14	0.1268	−0.0409	0.1684	0.075*
C15	0.2337 (4)	0.0377 (2)	0.27630 (16)	0.0505 (6)
H15	0.2827	0.0911	0.2487	0.061*
C16	0.1467 (4)	0.4537 (2)	0.6365 (2)	0.0653 (8)
H16A	0.1440	0.5135	0.6718	0.098*
H16B	0.0233	0.4308	0.6151	0.098*
H16C	0.2051	0.4691	0.5874	0.098*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.0782 (2)	0.0677 (2)	0.0682 (2)	−0.02565 (16)	0.01984 (16)	−0.00776 (15)
O1	0.0553 (11)	0.0908 (15)	0.0412 (10)	0.0213 (10)	−0.0016 (9)	−0.0095 (9)
N1	0.0486 (12)	0.0437 (11)	0.0354 (10)	0.0023 (9)	0.0121 (9)	−0.0012 (8)
N2	0.0599 (13)	0.0571 (13)	0.0371 (10)	−0.0003 (11)	0.0126 (10)	0.0017 (9)
N3	0.0589 (14)	0.0539 (13)	0.0482 (12)	−0.0028 (11)	0.0149 (10)	0.0058 (10)
C1	0.0396 (13)	0.0474 (14)	0.0477 (13)	−0.0048 (10)	0.0130 (11)	−0.0054 (11)
C2	0.0535 (15)	0.0589 (16)	0.0506 (14)	−0.0108 (13)	0.0224 (12)	−0.0199 (13)
C3	0.0554 (16)	0.0745 (19)	0.0353 (13)	−0.0196 (14)	0.0119 (12)	−0.0076 (13)
C4	0.0555 (15)	0.0566 (16)	0.0381 (13)	−0.0099 (13)	0.0021 (11)	0.0032 (12)
C5	0.0477 (14)	0.0475 (14)	0.0417 (13)	−0.0013 (11)	0.0051 (11)	−0.0037 (11)
C6	0.0377 (12)	0.0418 (13)	0.0359 (11)	−0.0049 (10)	0.0065 (10)	−0.0051 (10)
C7	0.0435 (13)	0.0435 (13)	0.0360 (12)	0.0040 (10)	0.0051 (11)	−0.0024 (10)
C8	0.0457 (14)	0.0461 (13)	0.0377 (12)	−0.0011 (11)	0.0077 (10)	−0.0009 (10)
C9	0.0521 (14)	0.0479 (14)	0.0383 (12)	0.0001 (11)	0.0160 (11)	−0.0013 (10)
C10	0.0375 (12)	0.0447 (13)	0.0405 (12)	0.0084 (10)	0.0076 (10)	−0.0027 (10)
C11	0.0397 (13)	0.0487 (14)	0.0499 (14)	0.0052 (11)	0.0092 (11)	−0.0006 (11)
C12	0.0495 (16)	0.0524 (17)	0.0736 (19)	−0.0038 (12)	0.0136 (14)	−0.0045 (14)
C13	0.0546 (17)	0.0663 (19)	0.072 (2)	−0.0022 (14)	0.0026 (15)	−0.0244 (16)
C14	0.0628 (18)	0.074 (2)	0.0473 (15)	0.0079 (15)	0.0034 (13)	−0.0142 (14)
C15	0.0572 (16)	0.0540 (16)	0.0412 (13)	0.0067 (12)	0.0121 (12)	−0.0003 (11)
C16	0.0717 (19)	0.0544 (17)	0.0706 (19)	0.0143 (14)	0.0156 (15)	−0.0045 (14)

Geometric parameters (Å, º)

Br1—C8	1.953 (2)	C7—C8	1.519 (3)
O1—C7	1.209 (3)	C8—C9	1.513 (3)
N1—N2	1.351 (3)	C8—H8	0.98
N1—C10	1.355 (3)	C9—H9A	0.97
N1—C9	1.456 (3)	C9—H9B	0.97
N2—N3	1.308 (3)	C10—C11	1.388 (3)
N3—C11	1.382 (3)	C10—C15	1.403 (3)
C1—C2	1.401 (4)	C11—C12	1.396 (4)
C1—C6	1.404 (3)	C12—C13	1.361 (4)
C1—C16	1.500 (4)	C12—H12	0.93
C2—C3	1.374 (4)	C13—C14	1.402 (4)
C2—H2	0.93	C13—H13	0.93
C3—C4	1.370 (4)	C14—C15	1.370 (4)
C3—H3	0.93	C14—H14	0.93
C4—C5	1.382 (3)	C15—H15	0.93
C4—H4	0.93	C16—H16A	0.96
C5—C6	1.390 (3)	C16—H16B	0.96
C5—H5	0.93	C16—H16C	0.96
C6—C7	1.490 (3)
N2—N1—C10	110.18 (19)	Br1—C8—H8	109.8
N2—N1—C9	121.12 (19)	N1—C9—C8	110.40 (18)
C10—N1—C9	128.68 (18)	N1—C9—H9A	109.6
N3—N2—N1	109.20 (19)	C8—C9—H9A	109.6
N2—N3—C11	107.5 (2)	N1—C9—H9B	109.6
C2—C1—C6	117.2 (2)	C8—C9—H9B	109.6
C2—C1—C16	119.3 (2)	H9A—C9—H9B	108.1
C6—C1—C16	123.5 (2)	N1—C10—C11	104.53 (19)
C3—C2—C1	122.2 (2)	N1—C10—C15	133.4 (2)
C3—C2—H2	118.9	C11—C10—C15	122.1 (2)
C1—C2—H2	118.9	N3—C11—C10	108.5 (2)
C4—C3—C2	120.0 (2)	N3—C11—C12	130.5 (2)
C4—C3—H3	120.0	C10—C11—C12	120.9 (2)
C2—C3—H3	120.0	C13—C12—C11	116.9 (3)
C3—C4—C5	119.5 (2)	C13—C12—H12	121.6
C3—C4—H4	120.2	C11—C12—H12	121.6
C5—C4—H4	120.2	C12—C13—C14	122.3 (3)
C4—C5—C6	121.1 (2)	C12—C13—H13	118.8
C4—C5—H5	119.4	C14—C13—H13	118.8
C6—C5—H5	119.4	C15—C14—C13	121.8 (3)
C5—C6—C1	119.9 (2)	C15—C14—H14	119.1
C5—C6—C7	119.3 (2)	C13—C14—H14	119.1
C1—C6—C7	120.8 (2)	C14—C15—C10	116.0 (3)
O1—C7—C6	122.6 (2)	C14—C15—H15	122.0
O1—C7—C8	119.2 (2)	C10—C15—H15	122.0
C6—C7—C8	118.10 (19)	C1—C16—H16A	109.5
C9—C8—C7	114.2 (2)	C1—C16—H16B	109.5
C9—C8—Br1	107.75 (15)	H16A—C16—H16B	109.5
C7—C8—Br1	105.22 (16)	C1—C16—H16C	109.5
C9—C8—H8	109.8	H16A—C16—H16C	109.5
C7—C8—H8	109.8	H16B—C16—H16C	109.5
C10—N1—N2—N3	−0.9 (3)	N2—N1—C9—C8	−5.8 (3)
C9—N1—N2—N3	−179.9 (2)	C10—N1—C9—C8	175.4 (2)
N1—N2—N3—C11	0.2 (3)	C7—C8—C9—N1	−69.1 (3)
C6—C1—C2—C3	−1.6 (4)	Br1—C8—C9—N1	174.40 (16)
C16—C1—C2—C3	−179.1 (2)	N2—N1—C10—C11	1.1 (2)
C1—C2—C3—C4	0.8 (4)	C9—N1—C10—C11	−180.0 (2)
C2—C3—C4—C5	0.7 (4)	N2—N1—C10—C15	−179.8 (3)
C3—C4—C5—C6	−1.3 (4)	C9—N1—C10—C15	−0.9 (4)
C4—C5—C6—C1	0.5 (4)	N2—N3—C11—C10	0.5 (3)
C4—C5—C6—C7	−179.0 (2)	N2—N3—C11—C12	−178.9 (3)
C2—C1—C6—C5	0.9 (3)	N1—C10—C11—N3	−1.0 (2)
C16—C1—C6—C5	178.3 (2)	C15—C10—C11—N3	179.8 (2)
C2—C1—C6—C7	−179.6 (2)	N1—C10—C11—C12	178.5 (2)
C16—C1—C6—C7	−2.3 (4)	C15—C10—C11—C12	−0.7 (4)
C5—C6—C7—O1	142.3 (3)	N3—C11—C12—C13	179.8 (3)
C1—C6—C7—O1	−37.2 (4)	C10—C11—C12—C13	0.4 (4)
C5—C6—C7—C8	−39.3 (3)	C11—C12—C13—C14	0.3 (4)
C1—C6—C7—C8	141.3 (2)	C12—C13—C14—C15	−0.8 (5)
O1—C7—C8—C9	−22.9 (3)	C13—C14—C15—C10	0.5 (4)
C6—C7—C8—C9	158.6 (2)	N1—C10—C15—C14	−178.7 (3)
O1—C7—C8—Br1	95.1 (2)	C11—C10—C15—C14	0.2 (4)
C6—C7—C8—Br1	−83.4 (2)