3-(Benzotriazol-1-yl)-2,2-dibromo-1-(2-chloro­phen­yl)propan-1-one

In the title compound, C₁₅H₁₀Br₂ClN₃O, the benzotriazole mean plane makes a dihedral angle of 57.09 (1)° with the other benzene ring. In the crystal structure, the packing is stabilized by C—H...π inter­actions, together with close Br...N and Br...Br inter­actions [3.292 (3), 3.054 (3), 3.279 (3) and 3.571 (1) Å].

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.027
• wR factor = 0.071
• Data-to-parameter ratio = 14.9

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT431_ALERT_2_B Short Inter HL..A Contact  Br1    ..  N3      ..       3.05 Ang.

Alert level C
ABSTM02_ALERT_3_C  The ratio of expected to reported Tmax/Tmin(RR) is > 1.10
            Tmin and Tmax reported:      0.361     0.738
            Tmin and Tmax expected:      0.286     0.731
            RR =      1.252
            Please check that your absorption correction is appropriate.
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.97
PLAT060_ALERT_3_C Ratio Tmax/Tmin (Exp-to-Rep) (too) Large .......       1.27
PLAT154_ALERT_1_C The su's on the Cell Angles are Equal  (x 10000)        300 Deg.
PLAT431_ALERT_2_C Short Inter HL..A Contact  Br1    ..  N2      ..       3.29 Ang.
PLAT431_ALERT_2_C Short Inter HL..A Contact  Br2    ..  Br2     ..       3.57 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
   1 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
   3 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 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

Recently we reported the structure of 2-(1H-1,2,3-benzotriazol-1-yl)-1-benzoylethyl 2-chlorobenzoate (II) (Wan et al., 2006). As part of our ongoing investigation of triazole derivatives with greater pharmacological activity, the title compound, (I), was synthesized and its structure is presented here, Fig. 1.

In the title compound (I), all bond lengths and angles are within normal ranges (Allen et al., 1987) and are comparable to those in the related compound, (II). The whole molecule is non-planar with a dihedral angle of 57.09 (1)° between the C10—C15 benzene ring and N1—N3/C1—C6 benzotriazole ring. The benzotriazole system is essentially planar with a dihedral angle of 3.27 (2)° between the N1—N3/C1/C6 triazole ring and C1—C6 benzene ring.

In the crystal structure, the packing is stabilized by C—H···π interactions (Table 1) and weak Br···N and Br···Br van der Waals forces with the distances Br1···N2, Br1···N3, Br2—N2 and Br2—Br2 of 3.292 (3), 3.054 (3), 3.279 (3) and 3.571 (1) Å, respectively.

Related literature

For a related structure, see: Wan et al. (2006) and for reference structural 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 six days.

S3. Refinement

All H-atoms were positioned geometrically and refined using a riding model with d(C—H) = 0.93 Å, U_iso=1.2U_eq (C) for aromatic and 0.97 Å, U_iso = 1.2U_eq (C) for CH₂ atoms.

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 structure of the compound (I) showing 50% probability displacement ellipsoids and the atom numbering scheme.
	Fig. 2. A packing diagram of (I), viewed down the a axis

3-(Benzotriazol-1-yl)-2,2-dibromo-1-(2-chlorophenyl)propan-1-one

Crystal data

C15H10Br2ClN3O	Z = 2
Mr = 443.53	F(000) = 432
Triclinic, P1	Dx = 1.837 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.7509 (18) Å	Cell parameters from 2538 reflections
b = 9.182 (2) Å	θ = 2.4–25.6°
c = 12.563 (3) Å	µ = 5.22 mm^−1
α = 73.058 (3)°	T = 293 K
β = 76.442 (3)°	Plate, colourless
γ = 71.700 (3)°	0.25 × 0.23 × 0.06 mm
V = 801.9 (3) Å^3

Data collection

Siemens SMART 1000 CCD area detector diffractometer	2964 independent reflections
Radiation source: fine-focus sealed tube	2528 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.012
Detector resolution: 8.33 pixels mm^-1	θmax = 25.7°, θmin = 1.7°
ω scans	h = −6→9
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −11→11
Tmin = 0.361, Tmax = 0.738	l = −15→14
4374 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)] = 0.027	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.071	H-atom parameters constrained
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0397P)^2 + 0.2687P] where P = (Fo^2 + 2Fc^2)/3
2964 reflections	(Δ/σ)max < 0.001
199 parameters	Δρmax = 0.69 e Å^−3
0 restraints	Δρmin = −0.59 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	0.10429 (4)	0.39211 (3)	0.34085 (2)	0.04875 (11)
Br2	0.44143 (4)	0.43973 (3)	0.14942 (2)	0.05179 (11)
Cl1	0.34216 (14)	0.86655 (11)	0.01049 (10)	0.0815 (3)
N1	0.5040 (3)	0.4005 (3)	0.39885 (19)	0.0444 (5)
N2	0.6829 (3)	0.3765 (3)	0.3484 (2)	0.0556 (6)
N3	0.7793 (3)	0.2462 (3)	0.4054 (2)	0.0594 (7)
O1	0.0957 (3)	0.7883 (3)	0.2727 (2)	0.0677 (6)
C1	0.4867 (4)	0.2817 (3)	0.4925 (2)	0.0414 (6)
C2	0.3399 (4)	0.2528 (4)	0.5773 (3)	0.0541 (7)
H2	0.2212	0.3188	0.5761	0.065*
C3	0.3822 (5)	0.1211 (4)	0.6622 (3)	0.0712 (10)
H3	0.2884	0.0968	0.7200	0.085*
C4	0.5594 (5)	0.0216 (4)	0.6660 (3)	0.0731 (10)
H4	0.5804	−0.0659	0.7263	0.088*
C5	0.7018 (5)	0.0493 (4)	0.5840 (3)	0.0634 (9)
H5	0.8198	−0.0176	0.5864	0.076*
C6	0.6638 (4)	0.1829 (3)	0.4955 (3)	0.0474 (7)
C7	0.3712 (4)	0.5435 (3)	0.3528 (2)	0.0443 (6)
H7A	0.4347	0.6252	0.3163	0.053*
H7B	0.2812	0.5782	0.4146	0.053*
C8	0.2698 (3)	0.5274 (3)	0.2683 (2)	0.0396 (6)
C9	0.1419 (4)	0.6891 (3)	0.2196 (2)	0.0443 (6)
C10	0.0762 (4)	0.7164 (3)	0.1099 (2)	0.0465 (7)
C11	0.1573 (4)	0.7987 (3)	0.0101 (3)	0.0574 (8)
C12	0.0944 (6)	0.8256 (4)	−0.0910 (3)	0.0786 (12)
H12	0.1506	0.8800	−0.1578	0.094*
C13	−0.0504 (7)	0.7714 (5)	−0.0909 (4)	0.0878 (13)
H13	−0.0920	0.7881	−0.1582	0.105*
C14	−0.1343 (6)	0.6934 (5)	0.0063 (4)	0.0781 (11)
H14	−0.2346	0.6593	0.0050	0.094*
C15	−0.0727 (4)	0.6640 (4)	0.1074 (3)	0.0589 (8)
H15	−0.1306	0.6095	0.1735	0.071*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.04169 (17)	0.04869 (18)	0.05735 (19)	−0.01748 (12)	−0.00454 (13)	−0.01130 (13)
Br2	0.04431 (17)	0.05571 (19)	0.04718 (18)	−0.00010 (13)	0.00003 (12)	−0.01991 (13)
Cl1	0.0693 (6)	0.0616 (5)	0.1009 (7)	−0.0246 (4)	0.0143 (5)	−0.0143 (5)
N1	0.0339 (12)	0.0526 (14)	0.0472 (13)	−0.0139 (10)	−0.0044 (10)	−0.0116 (11)
N2	0.0350 (13)	0.0698 (17)	0.0593 (16)	−0.0190 (12)	−0.0050 (11)	−0.0073 (13)
N3	0.0387 (13)	0.0676 (17)	0.0655 (17)	−0.0140 (12)	−0.0068 (12)	−0.0069 (14)
O1	0.0695 (15)	0.0545 (13)	0.0823 (17)	0.0054 (11)	−0.0242 (13)	−0.0349 (12)
C1	0.0414 (15)	0.0452 (15)	0.0423 (14)	−0.0140 (12)	−0.0050 (12)	−0.0158 (12)
C2	0.0463 (17)	0.0572 (18)	0.0503 (17)	−0.0078 (14)	0.0013 (13)	−0.0132 (14)
C3	0.065 (2)	0.069 (2)	0.062 (2)	−0.0191 (18)	0.0106 (17)	−0.0047 (18)
C4	0.073 (2)	0.053 (2)	0.072 (2)	−0.0104 (17)	−0.0037 (19)	0.0046 (17)
C5	0.0552 (19)	0.0501 (18)	0.077 (2)	−0.0038 (15)	−0.0121 (17)	−0.0122 (16)
C6	0.0411 (15)	0.0466 (16)	0.0565 (17)	−0.0120 (12)	−0.0048 (13)	−0.0169 (13)
C7	0.0434 (15)	0.0438 (15)	0.0499 (16)	−0.0140 (12)	−0.0075 (12)	−0.0145 (12)
C8	0.0338 (13)	0.0414 (14)	0.0434 (14)	−0.0110 (11)	0.0020 (11)	−0.0148 (11)
C9	0.0343 (14)	0.0457 (15)	0.0518 (16)	−0.0098 (11)	−0.0011 (12)	−0.0152 (13)
C10	0.0427 (15)	0.0410 (15)	0.0500 (16)	0.0001 (12)	−0.0076 (13)	−0.0139 (12)
C11	0.0537 (18)	0.0425 (16)	0.062 (2)	0.0004 (13)	−0.0004 (15)	−0.0129 (14)
C12	0.103 (3)	0.057 (2)	0.050 (2)	0.009 (2)	−0.012 (2)	−0.0064 (16)
C13	0.106 (4)	0.080 (3)	0.072 (3)	0.010 (2)	−0.043 (3)	−0.024 (2)
C14	0.070 (2)	0.073 (2)	0.098 (3)	0.0038 (19)	−0.043 (2)	−0.031 (2)
C15	0.0494 (18)	0.0570 (19)	0.070 (2)	−0.0050 (14)	−0.0172 (15)	−0.0174 (16)

Geometric parameters (Å, º)

Br1—C8	1.952 (3)	C5—C6	1.400 (4)
Br2—C8	1.935 (3)	C5—H5	0.9300
Cl1—C11	1.734 (4)	C7—C8	1.524 (4)
N1—N2	1.360 (3)	C7—H7A	0.9700
N1—C1	1.364 (4)	C7—H7B	0.9700
N1—C7	1.451 (3)	C8—C9	1.547 (4)
N2—N3	1.301 (4)	C9—C10	1.507 (4)
N3—C6	1.374 (4)	C10—C11	1.384 (4)
O1—C9	1.200 (3)	C10—C15	1.392 (4)
C1—C6	1.390 (4)	C11—C12	1.394 (5)
C1—C2	1.399 (4)	C12—C13	1.362 (6)
C2—C3	1.368 (5)	C12—H12	0.9300
C2—H2	0.9300	C13—C14	1.355 (6)
C3—C4	1.393 (5)	C13—H13	0.9300
C3—H3	0.9300	C14—C15	1.385 (5)
C4—C5	1.355 (5)	C14—H14	0.9300
C4—H4	0.9300	C15—H15	0.9300
N2—N1—C1	109.8 (2)	H7A—C7—H7B	107.5
N2—N1—C7	118.7 (2)	C7—C8—C9	110.2 (2)
C1—N1—C7	131.4 (2)	C7—C8—Br2	110.90 (17)
N3—N2—N1	108.8 (2)	C9—C8—Br2	111.06 (19)
N2—N3—C6	108.5 (2)	C7—C8—Br1	111.43 (18)
N1—C1—C6	104.4 (2)	C9—C8—Br1	104.46 (17)
N1—C1—C2	133.8 (3)	Br2—C8—Br1	108.57 (13)
C6—C1—C2	121.8 (3)	O1—C9—C10	122.2 (3)
C3—C2—C1	115.7 (3)	O1—C9—C8	118.0 (3)
C3—C2—H2	122.2	C10—C9—C8	119.8 (2)
C1—C2—H2	122.2	C11—C10—C15	118.4 (3)
C2—C3—C4	123.0 (3)	C11—C10—C9	121.1 (3)
C2—C3—H3	118.5	C15—C10—C9	120.4 (3)
C4—C3—H3	118.5	C10—C11—C12	120.9 (4)
C5—C4—C3	121.5 (3)	C10—C11—Cl1	119.5 (3)
C5—C4—H4	119.3	C12—C11—Cl1	119.6 (3)
C3—C4—H4	119.3	C13—C12—C11	119.3 (4)
C4—C5—C6	117.2 (3)	C13—C12—H12	120.3
C4—C5—H5	121.4	C11—C12—H12	120.3
C6—C5—H5	121.4	C14—C13—C12	120.7 (4)
N3—C6—C1	108.5 (3)	C14—C13—H13	119.6
N3—C6—C5	130.6 (3)	C12—C13—H13	119.6
C1—C6—C5	120.9 (3)	C13—C14—C15	120.9 (4)
N1—C7—C8	115.0 (2)	C13—C14—H14	119.6
N1—C7—H7A	108.5	C15—C14—H14	119.6
C8—C7—H7A	108.5	C14—C15—C10	119.7 (4)
N1—C7—H7B	108.5	C14—C15—H15	120.1
C8—C7—H7B	108.5	C10—C15—H15	120.1

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7A···Cg2^i	0.97	2.87	3.523	126
C7—H7B···Cg1^i	0.97	2.88	3.484	122

Symmetry code: (i) −x+1, −y+1, −z+1.