3-(1H-Benzotriazol-1-yl)-1-(4-bromo­phen­yl)propan-1-one

In the mol­ecule of the title compound, C₁₅H₁₂BrN₃O, the dihedral angle between the benzotriazole ring system and the benzene ring is 19.0 (1)°. π–π inter­actions stabilize the crystal structure (centroid-to-centroid distances of 3.729 and 3.690 Å).

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.028
• wR factor = 0.073
• Data-to-parameter ratio = 13.3

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.97
PLAT180_ALERT_3_C Check Cell Rounding: # of Values Ending with 0 =          3
PLAT431_ALERT_2_C Short Inter HL..A Contact  Br1    ..  N2      ..       3.28 Ang.
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          1
              C15 H12 Br N3 O

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

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 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

Recently we have reported the strucure of 3-(1H-benzotriazol-1-yl)-1-(4-chloro- phenyl)-propan-1-one (Wan et al., 2006). As part of a search for new benzo- triazole compounds with higher bioactivity, the title compound, (I), was synthesized and its structure is presented here.

In the molecule of the title compound, (I) (Fig. 1), the bond lengths and angles are within normal ranges (Allen et al., 1987). The benzotriazole ring system is essentially planar, with a dihedral angle of 0.35 (1)° between the A (N1—N3/C10/C11) and B (C10—C15) rings. The mean planes of the benzotriazole ring system and the C (C1—C6) benzene ring make a dihedral angle of 19.0 (1)°.

The crystal packing is stabilized by π-π interactions involving the benzotriazole rings, with Cg1···Cg3ⁱ [symmetry code: (i) -x, -2 - y, 1 - z] and Cg2···Cg2ⁱⁱ [symmetry code: (ii) 1 - x, -1 - y, -z] distances of 3.729 and 3.690 Å, where Cg1, Cg2 and Cg3 denote the centroids of the A, C and B rings, respectively.

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 (Wan et al., 2006). Single crystals suitable for X-ray diffracion were obtained by slow evaporation of a dichloromethane-cyclohexane (1:2 v/v) solution at room temperature over a period of one week.

S3. Refinement

H atoms were located in difference syntheses with C—H = 0.9294–0.9301 Å and 0.9690–1.0155 Å, for aromatic and methylene H atoms, and constrained to ride on their parent atoms, with U_iso(H) = 1.2 U_eq(C).

Computing details

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

Figures

	Fig. 1. The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. A packing diagram of (I), viewed down the a axis.

3-(1H-Benzotriazol-1-yl)-1-(4-bromophenyl)propan-1-one

Crystal data

C15H12BrN3O	Z = 2
Mr = 330.18	F(000) = 332
Triclinic, P1	Dx = 1.631 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.2310 (8) Å	Cell parameters from 2068 reflections
b = 8.1517 (9) Å	θ = 3.0–26.0°
c = 12.5240 (14) Å	µ = 3.06 mm^−1
α = 101.671 (2)°	T = 298 K
β = 101.197 (1)°	Block, colourless
γ = 105.443 (2)°	0.29 × 0.22 × 0.19 mm
V = 672.37 (13) Å^3

Data collection

Siemens SMART 1000 CCD area-detector diffractometer	2563 independent reflections
Radiation source: fine-focus sealed tube	2232 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.011
Detector resolution: 8.33 pixels mm^-1	θmax = 26.0°, θmin = 1.7°
ω scans	h = −8→8
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −9→10
Tmin = 0.443, Tmax = 0.559	l = −15→11
3771 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)] = 0.028	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.073	H-atom parameters constrained
S = 1.06	w = 1/[σ^2(Fo^2) + (0.042P)^2 + 0.1157P] where P = (Fo^2 + 2Fc^2)/3
2563 reflections	(Δ/σ)max < 0.001
193 parameters	Δρmax = 0.27 e Å^−3
0 restraints	Δρmin = −0.29 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	0.28029 (3)	−0.23329 (3)	−0.11369 (2)	0.05799 (11)
O2	0.3769 (3)	−0.6149 (2)	0.32203 (14)	0.0613 (4)
N1	0.0217 (3)	−0.9405 (2)	0.32633 (15)	0.0457 (4)
N2	−0.1692 (3)	−1.0275 (3)	0.26609 (17)	0.0558 (5)
N3	−0.2874 (3)	−0.9779 (3)	0.32235 (18)	0.0589 (5)
C1	0.2135 (3)	−0.6601 (3)	0.0221 (2)	0.0503 (5)
H1A	0.1607	−0.7824	−0.0050	0.073 (8)*
C2	0.2099 (3)	−0.5576 (3)	−0.05288 (19)	0.0514 (5)
H2A	0.1554	−0.6106	−0.1299	0.077 (9)*
C3	0.2880 (3)	−0.3772 (3)	−0.01208 (18)	0.0430 (5)
C4	0.3753 (3)	−0.2969 (3)	0.10188 (19)	0.0471 (5)
H4A	0.4315	−0.1748	0.1282	0.055 (7)*
C5	0.3773 (3)	−0.4006 (3)	0.17583 (19)	0.0448 (5)
H5A	0.4350	−0.3473	0.2525	0.056 (7)*
C6	0.2948 (3)	−0.5835 (3)	0.13774 (18)	0.0411 (5)
C7	0.2992 (3)	−0.6880 (3)	0.22262 (19)	0.0446 (5)
C8	0.2046 (4)	−0.8864 (3)	0.1827 (2)	0.0505 (5)
H8A	0.2851	−0.9369	0.1410	0.057 (7)*
H8B	0.0746	−0.9146	0.1316	0.059 (7)*
C9	0.1821 (4)	−0.9721 (3)	0.2790 (2)	0.0524 (5)
H9A	0.1653	−1.0996	0.2524	0.067 (8)*
H9B	0.3119	−0.9249	0.3407	0.052 (7)*
C10	0.0277 (3)	−0.8309 (3)	0.42539 (18)	0.0423 (5)
C11	−0.1714 (3)	−0.8559 (3)	0.42249 (19)	0.0482 (5)
C12	−0.2241 (4)	−0.7626 (4)	0.5121 (2)	0.0611 (6)
H12A	−0.3564	−0.7784	0.5115	0.061 (7)*
C13	−0.0732 (4)	−0.6475 (4)	0.6006 (2)	0.0613 (6)
H13A	−0.1040	−0.5826	0.6608	0.073 (8)*
C14	0.1265 (4)	−0.6244 (3)	0.6022 (2)	0.0581 (6)
H14A	0.2248	−0.5461	0.6646	0.070 (8)*
C15	0.1821 (3)	−0.7127 (3)	0.51643 (19)	0.0507 (5)
H15A	0.3150	−0.6956	0.5179	0.063 (7)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.05417 (16)	0.06219 (18)	0.06435 (18)	0.01952 (12)	0.01661 (12)	0.02925 (12)
O2	0.0661 (11)	0.0559 (10)	0.0493 (10)	0.0036 (8)	0.0094 (8)	0.0133 (8)
N1	0.0457 (10)	0.0418 (9)	0.0487 (10)	0.0109 (8)	0.0123 (8)	0.0144 (8)
N2	0.0493 (11)	0.0533 (11)	0.0540 (11)	0.0051 (9)	0.0076 (9)	0.0117 (9)
N3	0.0442 (11)	0.0648 (13)	0.0596 (13)	0.0081 (10)	0.0077 (10)	0.0173 (10)
C1	0.0532 (13)	0.0382 (11)	0.0496 (13)	0.0046 (10)	0.0132 (10)	0.0035 (9)
C2	0.0534 (13)	0.0493 (13)	0.0418 (12)	0.0064 (10)	0.0098 (10)	0.0067 (10)
C3	0.0366 (10)	0.0483 (12)	0.0481 (12)	0.0152 (9)	0.0150 (9)	0.0158 (9)
C4	0.0458 (12)	0.0379 (11)	0.0543 (13)	0.0114 (9)	0.0133 (10)	0.0072 (9)
C5	0.0420 (11)	0.0440 (11)	0.0432 (12)	0.0120 (9)	0.0104 (9)	0.0039 (9)
C6	0.0349 (10)	0.0437 (11)	0.0455 (12)	0.0129 (9)	0.0151 (9)	0.0088 (9)
C7	0.0383 (11)	0.0465 (12)	0.0487 (13)	0.0113 (9)	0.0162 (9)	0.0102 (10)
C8	0.0562 (14)	0.0446 (12)	0.0559 (13)	0.0191 (11)	0.0224 (11)	0.0131 (10)
C9	0.0576 (14)	0.0461 (12)	0.0626 (14)	0.0225 (11)	0.0230 (12)	0.0194 (11)
C10	0.0434 (11)	0.0423 (11)	0.0452 (12)	0.0134 (9)	0.0118 (9)	0.0205 (9)
C11	0.0426 (11)	0.0540 (13)	0.0516 (13)	0.0152 (10)	0.0120 (10)	0.0229 (10)
C12	0.0511 (14)	0.0776 (17)	0.0674 (16)	0.0289 (13)	0.0230 (12)	0.0287 (14)
C13	0.0735 (17)	0.0673 (16)	0.0539 (14)	0.0326 (14)	0.0254 (13)	0.0181 (12)
C14	0.0617 (15)	0.0608 (15)	0.0455 (13)	0.0138 (12)	0.0087 (11)	0.0133 (11)
C15	0.0423 (12)	0.0592 (14)	0.0475 (13)	0.0124 (10)	0.0068 (10)	0.0172 (11)

Geometric parameters (Å, º)

Br1—C3	1.900 (2)	C6—C7	1.491 (3)
O2—C7	1.213 (3)	C7—C8	1.512 (3)
N1—N2	1.355 (3)	C8—C9	1.524 (3)
N1—C10	1.360 (3)	C8—H8A	0.9691
N1—C9	1.458 (3)	C8—H8B	0.9690
N2—N3	1.301 (3)	C9—H9A	0.9915
N3—C11	1.381 (3)	C9—H9B	1.0155
C1—C2	1.379 (3)	C10—C11	1.391 (3)
C1—C6	1.393 (3)	C10—C15	1.401 (3)
C1—H1A	0.9296	C11—C12	1.399 (4)
C2—C3	1.373 (3)	C12—C13	1.365 (4)
C2—H2A	0.9301	C12—H12A	0.9294
C3—C4	1.384 (3)	C13—C14	1.402 (4)
C4—C5	1.375 (3)	C13—H13A	0.9298
C4—H4A	0.9301	C14—C15	1.357 (3)
C5—C6	1.391 (3)	C14—H14A	0.9296
C5—H5A	0.9298	C15—H15A	0.9295
N2—N1—C10	110.28 (18)	C9—C8—H8A	108.7
N2—N1—C9	119.08 (19)	C7—C8—H8B	109.1
C10—N1—C9	130.63 (19)	C9—C8—H8B	108.9
N3—N2—N1	109.04 (18)	H8A—C8—H8B	107.7
N2—N3—C11	107.97 (19)	N1—C9—C8	111.96 (19)
C2—C1—C6	121.1 (2)	N1—C9—H9A	112.6
C2—C1—H1A	119.5	C8—C9—H9A	109.3
C6—C1—H1A	119.5	N1—C9—H9B	109.6
C3—C2—C1	119.0 (2)	C8—C9—H9B	109.6
C3—C2—H2A	120.9	H9A—C9—H9B	103.3
C1—C2—H2A	120.1	N1—C10—C11	104.11 (19)
C2—C3—C4	121.4 (2)	N1—C10—C15	133.9 (2)
C2—C3—Br1	119.67 (17)	C11—C10—C15	122.0 (2)
C4—C3—Br1	118.90 (16)	N3—C11—C10	108.6 (2)
C5—C4—C3	119.0 (2)	N3—C11—C12	131.0 (2)
C5—C4—H4A	120.4	C10—C11—C12	120.4 (2)
C3—C4—H4A	120.7	C13—C12—C11	117.4 (2)
C4—C5—C6	121.1 (2)	C13—C12—H12A	121.2
C4—C5—H5A	119.3	C11—C12—H12A	121.4
C6—C5—H5A	119.6	C12—C13—C14	121.4 (2)
C5—C6—C1	118.4 (2)	C12—C13—H13A	119.2
C5—C6—C7	118.38 (19)	C14—C13—H13A	119.4
C1—C6—C7	123.24 (19)	C15—C14—C13	122.5 (2)
O2—C7—C6	120.5 (2)	C15—C14—H14A	118.7
O2—C7—C8	120.5 (2)	C13—C14—H14A	118.7
C6—C7—C8	118.92 (19)	C14—C15—C10	116.2 (2)
C7—C8—C9	113.2 (2)	C14—C15—H15A	121.9
C7—C8—H8A	109.1	C10—C15—H15A	121.9
C10—N1—N2—N3	0.2 (2)	C10—N1—C9—C8	−105.7 (3)
C9—N1—N2—N3	−178.81 (19)	C7—C8—C9—N1	74.2 (3)
N1—N2—N3—C11	−0.3 (3)	N2—N1—C10—C11	0.0 (2)
C6—C1—C2—C3	0.0 (4)	C9—N1—C10—C11	178.9 (2)
C1—C2—C3—C4	2.0 (3)	N2—N1—C10—C15	−179.5 (2)
C1—C2—C3—Br1	−178.90 (17)	C9—N1—C10—C15	−0.6 (4)
C2—C3—C4—C5	−2.2 (3)	N2—N3—C11—C10	0.4 (3)
Br1—C3—C4—C5	178.65 (16)	N2—N3—C11—C12	179.9 (3)
C3—C4—C5—C6	0.5 (3)	N1—C10—C11—N3	−0.2 (2)
C4—C5—C6—C1	1.4 (3)	C15—C10—C11—N3	179.3 (2)
C4—C5—C6—C7	−179.08 (19)	N1—C10—C11—C12	−179.8 (2)
C2—C1—C6—C5	−1.6 (3)	C15—C10—C11—C12	−0.2 (3)
C2—C1—C6—C7	178.9 (2)	N3—C11—C12—C13	−179.3 (3)
C5—C6—C7—O2	−1.6 (3)	C10—C11—C12—C13	0.2 (4)
C1—C6—C7—O2	177.9 (2)	C11—C12—C13—C14	−0.3 (4)
C5—C6—C7—C8	178.20 (19)	C12—C13—C14—C15	0.6 (4)
C1—C6—C7—C8	−2.3 (3)	C13—C14—C15—C10	−0.6 (4)
O2—C7—C8—C9	11.6 (3)	N1—C10—C15—C14	179.8 (2)
C6—C7—C8—C9	−168.27 (19)	C11—C10—C15—C14	0.4 (3)
N2—N1—C9—C8	73.1 (3)