2-(1H-1,2,3-Benzotriazol-1-yl)-1-m-toluoylethyl 2,4-dichloro-benzoate.

In the title compound, C(23)H(17)Cl(2)N(3)O(3), the dihedral angles between the mean planes of the benzotriazole system and the methyl- and dichloro-substituted benzene rings are 47.72 (1) and 13.06 (1)°, respectively. In the crystal structure, inter-molecular C-H⋯O and C-H⋯π inter-actions help to consolidate the packing.

Related literature

For background, see Chen & Wu (2005 ▶). For reference structural data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C23H17Cl2N3O3

M = 454.30

Monoclinic,

a = 9.3395 (19) Å

b = 9.3065 (19) Å

c = 23.538 (5) Å

β = 92.10 (3)°

V = 2044.5 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.35 mm−1

T = 113 (2) K

0.18 × 0.16 × 0.08 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 1997 ▶) T min = 0.940, T max = 0.973

11260 measured reflections

3585 independent reflections

3138 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.033

wR(F 2) = 0.091

S = 1.10

3585 reflections

281 parameters

H-atom parameters constrained

Δρmax = 0.24 e Å−3

Δρmin = −0.30 e Å−3

Data collection: SMART (Bruker, 1997 ▶); cell refinement: SAINT (Bruker, 1997 ▶); data reduction: SAINT; 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.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808011963/hb2721sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808011963/hb2721Isup2.hkl

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

C23H17Cl2N3O3	F000 = 936
Mr = 454.30	Dx = 1.476 Mg m−3
Monoclinic, P21/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5663 reflections
a = 9.3395 (19) Å	θ = 1.7–27.9º
b = 9.3065 (19) Å	µ = 0.35 mm−1
c = 23.538 (5) Å	T = 113 (2) K
β = 92.10 (3)º	Slab, colourless
V = 2044.5 (7) Å3	0.18 × 0.16 × 0.08 mm
Z = 4

Bruker SMART CCD diffractometer	3585 independent reflections
Radiation source: X-ray tube	3138 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.031
T = 113(2) K	θmax = 25.0º
ω scans	θmin = 2.4º
Absorption correction: multi-scan(SADABS; Bruker, 1997)	h = −11→10
Tmin = 0.940, Tmax = 0.973	k = −11→10
11260 measured reflections	l = −27→20

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.033	H-atom parameters constrained
wR(F2) = 0.091	w = 1/[σ2(Fo2) + (0.0569P)2 + 0.0675P] where P = (Fo2 + 2Fc2)/3
S = 1.10	(Δ/σ)max = 0.001
3585 reflections	Δρmax = 0.24 e Å−3
281 parameters	Δρmin = −0.30 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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
Cl1	0.16956 (4)	0.45085 (4)	0.044626 (17)	0.02736 (13)
Cl2	0.48958 (4)	0.53198 (5)	−0.135572 (17)	0.03077 (14)
O1	0.28238 (12)	1.07298 (12)	0.10792 (5)	0.0272 (3)
O2	0.37879 (10)	0.80863 (11)	0.11568 (4)	0.0208 (3)
O3	0.14534 (11)	0.76130 (12)	0.09646 (5)	0.0309 (3)
N1	0.58217 (13)	0.98801 (13)	0.18828 (6)	0.0199 (3)
N2	0.61195 (13)	1.10055 (14)	0.22405 (6)	0.0255 (3)
N3	0.71818 (13)	1.17383 (14)	0.20467 (6)	0.0279 (3)
C1	0.22159 (14)	1.10721 (16)	0.20360 (7)	0.0189 (3)
C2	0.18316 (15)	1.04219 (16)	0.25408 (7)	0.0194 (3)
H2	0.1983	0.9441	0.2590	0.023*
C3	0.12259 (14)	1.12125 (16)	0.29721 (7)	0.0209 (3)
C4	0.10223 (15)	1.26887 (16)	0.28894 (7)	0.0228 (4)
H4	0.0603	1.3232	0.3170	0.027*
C5	0.14371 (15)	1.33491 (17)	0.23954 (7)	0.0244 (4)
H5	0.1320	1.4336	0.2352	0.029*
C6	0.20216 (15)	1.25563 (16)	0.19677 (7)	0.0231 (4)
H6	0.2287	1.3004	0.1634	0.028*
C7	0.08028 (17)	1.05045 (18)	0.35132 (7)	0.0272 (4)
H7A	−0.0178	1.0198	0.3476	0.041*
H7B	0.0908	1.1176	0.3822	0.041*
H7C	0.1407	0.9687	0.3588	0.041*
C8	0.27983 (15)	1.02509 (16)	0.15583 (7)	0.0197 (3)
C9	0.34219 (15)	0.87504 (16)	0.16804 (6)	0.0198 (3)
H9	0.2707	0.8162	0.1867	0.024*
C10	0.26778 (15)	0.75666 (16)	0.08292 (7)	0.0213 (3)
C11	0.32137 (15)	0.69822 (16)	0.02907 (7)	0.0194 (3)
C12	0.28115 (15)	0.56368 (16)	0.00791 (7)	0.0193 (3)
C13	0.33423 (15)	0.51230 (17)	−0.04221 (6)	0.0212 (4)
H13	0.3086	0.4214	−0.0555	0.025*
C14	0.42553 (15)	0.59738 (17)	−0.07222 (7)	0.0221 (3)
C15	0.46799 (15)	0.73162 (17)	−0.05280 (7)	0.0239 (4)
H15	0.5301	0.7878	−0.0734	0.029*
C16	0.41582 (15)	0.77997 (17)	−0.00211 (7)	0.0220 (3)
H16	0.4445	0.8696	0.0116	0.026*
C17	0.47953 (15)	0.87985 (16)	0.20522 (7)	0.0210 (3)
H17A	0.4545	0.8983	0.2442	0.025*
H17B	0.5251	0.7863	0.2043	0.025*
C18	0.67506 (14)	0.98839 (16)	0.14484 (7)	0.0188 (3)
C19	0.69518 (16)	0.89704 (17)	0.09888 (7)	0.0227 (4)
H19	0.6366	0.8177	0.0919	0.027*
C20	0.80604 (16)	0.93045 (19)	0.06451 (8)	0.0300 (4)
H20	0.8227	0.8727	0.0332	0.036*
C21	0.89552 (17)	1.05053 (19)	0.07554 (8)	0.0342 (4)
H21	0.9701	1.0692	0.0515	0.041*
C22	0.87541 (16)	1.13949 (18)	0.12039 (8)	0.0301 (4)
H22	0.9346	1.2184	0.1273	0.036*
C23	0.76221 (15)	1.10800 (16)	0.15590 (7)	0.0239 (4)

	U11	U22	U33	U12	U13	U23
Cl1	0.0300 (2)	0.0263 (2)	0.0262 (2)	−0.00985 (15)	0.00706 (17)	−0.00106 (17)
Cl2	0.0362 (2)	0.0404 (3)	0.0161 (2)	0.00522 (17)	0.00562 (18)	−0.00085 (17)
O1	0.0329 (6)	0.0272 (6)	0.0216 (7)	−0.0044 (5)	0.0046 (5)	0.0035 (5)
O2	0.0188 (5)	0.0247 (6)	0.0192 (6)	−0.0027 (4)	0.0041 (4)	−0.0069 (5)
O3	0.0210 (6)	0.0373 (7)	0.0351 (8)	−0.0070 (5)	0.0090 (5)	−0.0115 (6)
N1	0.0210 (6)	0.0172 (6)	0.0214 (8)	0.0009 (5)	0.0001 (5)	−0.0044 (5)
N2	0.0260 (7)	0.0209 (7)	0.0294 (8)	0.0027 (5)	−0.0027 (6)	−0.0096 (6)
N3	0.0238 (7)	0.0219 (7)	0.0378 (9)	−0.0003 (5)	−0.0015 (6)	−0.0053 (7)
C1	0.0153 (7)	0.0201 (8)	0.0212 (9)	−0.0003 (6)	−0.0013 (6)	−0.0009 (7)
C2	0.0160 (7)	0.0183 (8)	0.0241 (9)	0.0002 (5)	0.0013 (6)	−0.0017 (7)
C3	0.0144 (7)	0.0257 (8)	0.0224 (9)	0.0005 (6)	−0.0013 (6)	−0.0035 (7)
C4	0.0166 (7)	0.0245 (8)	0.0271 (9)	0.0026 (6)	−0.0012 (6)	−0.0086 (7)
C5	0.0225 (8)	0.0176 (8)	0.0326 (10)	0.0027 (6)	−0.0056 (7)	−0.0015 (7)
C6	0.0209 (8)	0.0227 (8)	0.0253 (9)	−0.0012 (6)	−0.0028 (7)	0.0036 (7)
C7	0.0264 (8)	0.0320 (9)	0.0234 (9)	−0.0006 (7)	0.0050 (7)	−0.0050 (7)
C8	0.0166 (7)	0.0215 (8)	0.0210 (9)	−0.0056 (6)	0.0023 (6)	0.0008 (7)
C9	0.0225 (8)	0.0196 (8)	0.0176 (8)	−0.0022 (6)	0.0072 (6)	−0.0030 (6)
C10	0.0211 (8)	0.0195 (8)	0.0235 (9)	−0.0036 (6)	0.0029 (7)	−0.0005 (7)
C11	0.0174 (7)	0.0218 (8)	0.0188 (9)	0.0011 (6)	−0.0008 (6)	−0.0005 (7)
C12	0.0172 (7)	0.0213 (8)	0.0194 (8)	−0.0012 (6)	−0.0006 (6)	0.0026 (6)
C13	0.0239 (8)	0.0206 (8)	0.0189 (9)	0.0014 (6)	−0.0025 (7)	−0.0015 (7)
C14	0.0231 (8)	0.0293 (9)	0.0140 (8)	0.0059 (6)	0.0010 (6)	0.0024 (7)
C15	0.0231 (8)	0.0275 (9)	0.0211 (9)	−0.0013 (6)	0.0020 (7)	0.0063 (7)
C16	0.0228 (8)	0.0214 (8)	0.0217 (9)	−0.0023 (6)	0.0005 (7)	0.0014 (7)
C17	0.0242 (8)	0.0204 (8)	0.0185 (9)	0.0015 (6)	0.0038 (6)	−0.0006 (7)
C18	0.0164 (7)	0.0171 (7)	0.0230 (9)	0.0025 (6)	−0.0006 (6)	0.0016 (6)
C19	0.0208 (7)	0.0224 (8)	0.0249 (9)	−0.0005 (6)	0.0003 (7)	−0.0030 (7)
C20	0.0250 (8)	0.0346 (10)	0.0305 (10)	0.0012 (7)	0.0047 (7)	−0.0046 (8)
C21	0.0231 (9)	0.0382 (10)	0.0418 (12)	−0.0030 (7)	0.0100 (8)	0.0046 (9)
C22	0.0224 (8)	0.0237 (9)	0.0442 (12)	−0.0049 (6)	−0.0004 (8)	0.0019 (8)
C23	0.0209 (8)	0.0173 (8)	0.0332 (10)	0.0016 (6)	−0.0039 (7)	−0.0020 (7)

Cl1—C12	1.7326 (15)	C8—C9	1.536 (2)
Cl2—C14	1.7370 (16)	C9—C17	1.527 (2)
O1—C8	1.2136 (19)	C9—H9	0.9800
O2—C10	1.3582 (18)	C10—C11	1.483 (2)
O2—C9	1.4313 (18)	C11—C16	1.394 (2)
O3—C10	1.1990 (18)	C11—C12	1.394 (2)
N1—C18	1.365 (2)	C12—C13	1.382 (2)
N1—N2	1.3660 (18)	C13—C14	1.377 (2)
N1—C17	1.4557 (19)	C13—H13	0.9300
N2—N3	1.3004 (19)	C14—C15	1.383 (2)
N3—C23	1.377 (2)	C15—C16	1.381 (2)
C1—C2	1.392 (2)	C15—H15	0.9300
C1—C6	1.402 (2)	C16—H16	0.9300
C1—C8	1.480 (2)	C17—H17A	0.9700
C2—C3	1.391 (2)	C17—H17B	0.9700
C2—H2	0.9300	C18—C19	1.394 (2)
C3—C4	1.400 (2)	C18—C23	1.398 (2)
C3—C7	1.500 (2)	C19—C20	1.373 (2)
C4—C5	1.383 (2)	C19—H19	0.9300
C4—H4	0.9300	C20—C21	1.414 (2)
C5—C6	1.377 (2)	C20—H20	0.9300
C5—H5	0.9300	C21—C22	1.360 (3)
C6—H6	0.9300	C21—H21	0.9300
C7—H7A	0.9600	C22—C23	1.403 (2)
C7—H7B	0.9600	C22—H22	0.9300
C7—H7C	0.9600
C10—O2—C9	116.18 (11)	C16—C11—C12	118.02 (15)
C18—N1—N2	109.82 (12)	C16—C11—C10	119.32 (14)
C18—N1—C17	130.54 (13)	C12—C11—C10	122.67 (14)
N2—N1—C17	118.85 (13)	C13—C12—C11	121.03 (14)
N3—N2—N1	109.06 (13)	C13—C12—Cl1	117.22 (12)
N2—N3—C23	108.31 (13)	C11—C12—Cl1	121.69 (12)
C2—C1—C6	119.34 (14)	C14—C13—C12	119.16 (15)
C2—C1—C8	122.52 (14)	C14—C13—H13	120.4
C6—C1—C8	118.13 (14)	C12—C13—H13	120.4
C3—C2—C1	121.17 (14)	C13—C14—C15	121.67 (15)
C3—C2—H2	119.4	C13—C14—Cl2	118.56 (13)
C1—C2—H2	119.4	C15—C14—Cl2	119.77 (12)
C2—C3—C4	118.33 (15)	C16—C15—C14	118.29 (14)
C2—C3—C7	120.96 (14)	C16—C15—H15	120.9
C4—C3—C7	120.72 (14)	C14—C15—H15	120.9
C5—C4—C3	120.83 (15)	C15—C16—C11	121.81 (15)
C5—C4—H4	119.6	C15—C16—H16	119.1
C3—C4—H4	119.6	C11—C16—H16	119.1
C6—C5—C4	120.49 (15)	N1—C17—C9	114.27 (12)
C6—C5—H5	119.8	N1—C17—H17A	108.7
C4—C5—H5	119.8	C9—C17—H17A	108.7
C5—C6—C1	119.82 (15)	N1—C17—H17B	108.7
C5—C6—H6	120.1	C9—C17—H17B	108.7
C1—C6—H6	120.1	H17A—C17—H17B	107.6
C3—C7—H7A	109.5	N1—C18—C19	133.41 (14)
C3—C7—H7B	109.5	N1—C18—C23	104.14 (14)
H7A—C7—H7B	109.5	C19—C18—C23	122.41 (15)
C3—C7—H7C	109.5	C20—C19—C18	116.44 (15)
H7A—C7—H7C	109.5	C20—C19—H19	121.8
H7B—C7—H7C	109.5	C18—C19—H19	121.8
O1—C8—C1	122.46 (14)	C19—C20—C21	121.62 (17)
O1—C8—C9	119.18 (14)	C19—C20—H20	119.2
C1—C8—C9	118.34 (13)	C21—C20—H20	119.2
O2—C9—C17	106.50 (11)	C22—C21—C20	121.75 (16)
O2—C9—C8	109.41 (12)	C22—C21—H21	119.1
C17—C9—C8	112.67 (12)	C20—C21—H21	119.1
O2—C9—H9	109.4	C21—C22—C23	117.64 (15)
C17—C9—H9	109.4	C21—C22—H22	121.2
C8—C9—H9	109.4	C23—C22—H22	121.2
O3—C10—O2	123.50 (15)	N3—C23—C18	108.66 (14)
O3—C10—C11	126.53 (14)	N3—C23—C22	131.17 (14)
O2—C10—C11	109.96 (12)	C18—C23—C22	120.13 (15)
C18—N1—N2—N3	1.08 (16)	C10—C11—C12—Cl1	−2.4 (2)
C17—N1—N2—N3	171.98 (12)	C11—C12—C13—C14	−1.6 (2)
N1—N2—N3—C23	−1.23 (16)	Cl1—C12—C13—C14	−178.78 (11)
C6—C1—C2—C3	1.6 (2)	C12—C13—C14—C15	1.5 (2)
C8—C1—C2—C3	−177.02 (13)	C12—C13—C14—Cl2	−179.24 (11)
C1—C2—C3—C4	−0.6 (2)	C13—C14—C15—C16	−0.3 (2)
C1—C2—C3—C7	179.50 (13)	Cl2—C14—C15—C16	−179.58 (11)
C2—C3—C4—C5	−1.2 (2)	C14—C15—C16—C11	−0.8 (2)
C7—C3—C4—C5	178.73 (13)	C12—C11—C16—C15	0.7 (2)
C3—C4—C5—C6	1.9 (2)	C10—C11—C16—C15	−179.33 (13)
C4—C5—C6—C1	−0.9 (2)	C18—N1—C17—C9	−77.26 (19)
C2—C1—C6—C5	−0.9 (2)	N2—N1—C17—C9	114.04 (14)
C8—C1—C6—C5	177.82 (13)	O2—C9—C17—N1	74.44 (15)
C2—C1—C8—O1	162.53 (14)	C8—C9—C17—N1	−45.52 (17)
C6—C1—C8—O1	−16.1 (2)	N2—N1—C18—C19	177.33 (15)
C2—C1—C8—C9	−18.9 (2)	C17—N1—C18—C19	7.8 (3)
C6—C1—C8—C9	162.47 (13)	N2—N1—C18—C23	−0.46 (16)
C10—O2—C9—C17	162.00 (12)	C17—N1—C18—C23	−169.96 (14)
C10—O2—C9—C8	−75.96 (15)	N1—C18—C19—C20	−177.49 (16)
O1—C8—C9—O2	−7.23 (18)	C23—C18—C19—C20	0.0 (2)
C1—C8—C9—O2	174.12 (11)	C18—C19—C20—C21	0.5 (2)
O1—C8—C9—C17	111.04 (15)	C19—C20—C21—C22	−0.6 (3)
C1—C8—C9—C17	−67.61 (17)	C20—C21—C22—C23	0.2 (3)
C9—O2—C10—O3	−1.8 (2)	N2—N3—C23—C18	0.94 (17)
C9—O2—C10—C11	177.09 (12)	N2—N3—C23—C22	−176.75 (16)
O3—C10—C11—C16	130.70 (17)	N1—C18—C23—N3	−0.27 (17)
O2—C10—C11—C16	−48.10 (18)	C19—C18—C23—N3	−178.38 (13)
O3—C10—C11—C12	−49.3 (2)	N1—C18—C23—C22	177.72 (14)
O2—C10—C11—C12	131.91 (14)	C19—C18—C23—C22	−0.4 (2)
C16—C11—C12—C13	0.5 (2)	C21—C22—C23—N3	177.76 (16)
C10—C11—C12—C13	−179.47 (13)	C21—C22—C23—C18	0.3 (2)
C16—C11—C12—Cl1	177.60 (11)

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15···O1i	0.93	2.35	3.263 (2)	168
C4—H4···Cg1ii	0.93	2.86	3.4645 (19)	124

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C15—H15⋯O1i	0.93	2.35	3.263 (2)	168
C4—H4⋯Cg1ii	0.93	2.86	3.4645 (19)	124

Symmetry codes: (i) ; (ii) . Cg1 is the centroid of the C18–C23 ring.