2-(1H-1,2,3-Benzotriazol-1-yl)-1-(4-ethyl-benzo-yl)ethyl 2,4-dichloro-benzoate.

In the title mol-ecule, C(24)H(19)Cl(2)N(3), the dihedral angles between the benzotriazole group and the ethyl- and dichloro-substituted benzene rings are 16.53 (1) and 82.09 (1)°, respectively. The crystal structure is stabilized by weak inter-molecular C-H⋯O inter-actions.

Related literature

For related literature, see: Chen & Wu (2005 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C24H19Cl2N3O3

M = 468.32

Triclinic,

a = 9.251 (3) Å

b = 10.904 (4) Å

c = 11.057 (4) Å

α = 88.327 (6)°

β = 86.442 (6)°

γ = 83.304 (5)°

V = 1105.4 (6) Å3

Z = 2

Mo Kα radiation

μ = 0.33 mm−1

T = 298 (2) K

0.20 × 0.20 × 0.10 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 1997 ▶) T min = 0.938, T max = 0.991

5375 measured reflections

3700 independent reflections

2701 reflections with I > 2σ(I)

R int = 0.016

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.124

S = 1.03

3700 reflections

289 parameters

H-atom parameters constrained

Δρmax = 0.26 e Å−3

Δρmin = −0.34 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: PLATON (Spek, 2003 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808011951/lh2614sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808011951/lh2614Isup2.hkl

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

C24H19Cl2N3O3	Z = 2
Mr = 468.32	F000 = 484
Triclinic, P1	Dx = 1.407 Mg m−3
Hall symbol: -P 1	Mo Kα radiation λ = 0.71073 Å
a = 9.251 (3) Å	Cell parameters from 3700 reflections
b = 10.904 (4) Å	θ = 1.9–25.0º
c = 11.057 (4) Å	µ = 0.33 mm−1
α = 88.327 (6)º	T = 298 (2) K
β = 86.442 (6)º	Block, colorless
γ = 83.304 (5)º	0.20 × 0.20 × 0.10 mm
V = 1105.4 (6) Å3

Bruker SMART CCD area-detector diffractometer	3700 independent reflections
Radiation source: fine-focus sealed tube	2701 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.016
T = 298(2) K	θmax = 25.0º
φ and ω scans	θmin = 1.9º
Absorption correction: multi-scan(SADABS; Bruker, 1997)	h = −7→10
Tmin = 0.938, Tmax = 0.991	k = −12→12
5375 measured reflections	l = −10→12

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)] = 0.046	H-atom parameters constrained
wR(F2) = 0.124	w = 1/[σ2(Fo2) + (0.0528P)2 + 0.3617P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max < 0.001
3700 reflections	Δρmax = 0.26 e Å−3
289 parameters	Δρmin = −0.34 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	0.63408 (12)	0.54323 (8)	0.16704 (8)	0.0986 (4)
Cl2	0.17075 (9)	0.52373 (8)	0.46851 (10)	0.0910 (3)
N1	0.5431 (2)	0.10230 (19)	0.83967 (17)	0.0471 (5)
N2	0.4769 (3)	0.1341 (2)	0.9489 (2)	0.0609 (6)
N3	0.5560 (3)	0.2042 (2)	1.0028 (2)	0.0672 (7)
O1	0.1957 (2)	0.28033 (18)	0.58441 (18)	0.0651 (6)
O2	0.41844 (18)	0.18987 (15)	0.61852 (15)	0.0468 (4)
O3	0.3025 (2)	0.01135 (18)	0.51586 (16)	0.0608 (5)
C1	0.5439 (3)	0.4634 (3)	0.2799 (2)	0.0596 (8)
C2	0.4102 (3)	0.5146 (2)	0.3249 (2)	0.0577 (7)
H2B	0.3685	0.5899	0.2942	0.069*
C3	0.3380 (3)	0.4532 (2)	0.4161 (2)	0.0501 (6)
C4	0.4002 (3)	0.3419 (2)	0.4646 (2)	0.0436 (6)
C5	0.5355 (3)	0.2945 (2)	0.4167 (2)	0.0568 (7)
H5A	0.5794	0.2204	0.4483	0.068*
C6	0.6073 (4)	0.3530 (3)	0.3245 (3)	0.0694 (9)
H6A	0.6977	0.3184	0.2924	0.083*
C7	0.3240 (3)	0.2712 (2)	0.5603 (2)	0.0456 (6)
C8	0.3506 (3)	0.1039 (2)	0.6972 (2)	0.0439 (6)
H8A	0.2831	0.1483	0.7571	0.053*
C9	0.4734 (3)	0.0290 (2)	0.7597 (2)	0.0482 (6)
H9A	0.4352	−0.0383	0.8059	0.058*
H9B	0.5452	−0.0065	0.6990	0.058*
C10	0.6686 (3)	0.1556 (2)	0.8221 (2)	0.0431 (6)
C11	0.7727 (3)	0.1540 (2)	0.7266 (2)	0.0503 (6)
H11A	0.7664	0.1095	0.6570	0.060*
C12	0.8851 (3)	0.2213 (3)	0.7409 (3)	0.0601 (8)
H12A	0.9578	0.2228	0.6790	0.072*
C13	0.8951 (3)	0.2882 (3)	0.8449 (3)	0.0700 (9)
H13A	0.9738	0.3331	0.8504	0.084*
C14	0.7928 (4)	0.2892 (3)	0.9380 (3)	0.0692 (8)
H14A	0.7999	0.3340	1.0073	0.083*
C15	0.6762 (3)	0.2204 (2)	0.9264 (2)	0.0538 (7)
C16	0.2697 (3)	0.0221 (2)	0.6232 (2)	0.0431 (6)
C17	0.1553 (3)	−0.0460 (2)	0.6839 (2)	0.0411 (6)
C18	0.0778 (3)	−0.1156 (3)	0.6140 (2)	0.0562 (7)
H18A	0.1012	−0.1206	0.5311	0.067*
C19	−0.0327 (3)	−0.1769 (3)	0.6645 (3)	0.0643 (8)
H19A	−0.0826	−0.2233	0.6154	0.077*
C20	−0.0714 (3)	−0.1716 (3)	0.7863 (3)	0.0584 (7)
C21	0.0066 (3)	−0.1038 (3)	0.8564 (3)	0.0606 (8)
H21A	−0.0172	−0.0997	0.9392	0.073*
C22	0.1188 (3)	−0.0418 (2)	0.8074 (2)	0.0514 (7)
H22A	0.1699	0.0029	0.8572	0.062*
C23	−0.1960 (4)	−0.2369 (3)	0.8398 (4)	0.0919 (12)
H23A	−0.2398	−0.1926	0.9102	0.110*
H23B	−0.2696	−0.2351	0.7808	0.110*
C24	−0.1512 (5)	−0.3659 (4)	0.8759 (4)	0.1279 (18)
H24A	−0.2344	−0.4024	0.9103	0.192*
H24B	−0.0790	−0.3684	0.9349	0.192*
H24C	−0.1110	−0.4112	0.8061	0.192*

	U11	U22	U33	U12	U13	U23
Cl1	0.1231 (8)	0.0765 (6)	0.0850 (6)	0.0018 (5)	0.0436 (6)	0.0298 (5)
Cl2	0.0503 (5)	0.0744 (5)	0.1377 (8)	0.0148 (4)	0.0167 (5)	0.0406 (5)
N1	0.0510 (13)	0.0529 (12)	0.0360 (11)	−0.0061 (10)	0.0035 (10)	0.0096 (9)
N2	0.0689 (16)	0.0705 (16)	0.0410 (13)	−0.0087 (13)	0.0113 (12)	0.0072 (11)
N3	0.0821 (19)	0.0766 (17)	0.0422 (13)	−0.0113 (15)	0.0051 (13)	0.0002 (12)
O1	0.0416 (12)	0.0720 (13)	0.0788 (14)	−0.0037 (10)	0.0036 (9)	0.0222 (10)
O2	0.0430 (10)	0.0462 (10)	0.0507 (10)	−0.0075 (8)	−0.0010 (8)	0.0142 (8)
O3	0.0685 (13)	0.0705 (13)	0.0441 (11)	−0.0188 (10)	0.0123 (9)	−0.0010 (9)
C1	0.074 (2)	0.0521 (16)	0.0493 (16)	−0.0051 (15)	0.0089 (14)	0.0100 (13)
C2	0.0620 (19)	0.0476 (16)	0.0618 (18)	−0.0022 (14)	−0.0054 (14)	0.0154 (13)
C3	0.0428 (15)	0.0477 (15)	0.0590 (16)	−0.0023 (12)	−0.0059 (12)	0.0075 (12)
C4	0.0450 (14)	0.0429 (14)	0.0434 (14)	−0.0080 (11)	−0.0032 (11)	0.0038 (11)
C5	0.0624 (18)	0.0464 (15)	0.0559 (17)	0.0070 (13)	0.0107 (13)	0.0119 (13)
C6	0.074 (2)	0.0603 (18)	0.0643 (19)	0.0143 (16)	0.0231 (16)	0.0125 (15)
C7	0.0416 (15)	0.0445 (14)	0.0501 (15)	−0.0042 (11)	−0.0027 (12)	0.0037 (12)
C8	0.0447 (15)	0.0441 (14)	0.0419 (13)	−0.0077 (11)	0.0042 (11)	0.0090 (11)
C9	0.0530 (16)	0.0463 (14)	0.0451 (14)	−0.0090 (12)	0.0010 (12)	0.0078 (11)
C10	0.0456 (15)	0.0429 (13)	0.0392 (13)	−0.0006 (11)	−0.0033 (11)	0.0097 (11)
C11	0.0472 (16)	0.0512 (15)	0.0501 (16)	−0.0002 (12)	0.0030 (12)	0.0073 (12)
C12	0.0459 (16)	0.0578 (17)	0.074 (2)	−0.0024 (14)	0.0039 (14)	0.0090 (15)
C13	0.0560 (19)	0.0633 (19)	0.092 (2)	−0.0130 (15)	−0.0131 (18)	0.0106 (18)
C14	0.083 (2)	0.0620 (18)	0.066 (2)	−0.0107 (17)	−0.0198 (18)	−0.0055 (15)
C15	0.0627 (18)	0.0527 (16)	0.0453 (15)	−0.0022 (14)	−0.0088 (13)	0.0043 (12)
C16	0.0414 (14)	0.0424 (13)	0.0429 (15)	0.0001 (11)	0.0055 (11)	0.0058 (11)
C17	0.0401 (14)	0.0385 (13)	0.0428 (14)	−0.0008 (11)	0.0028 (11)	0.0042 (11)
C18	0.0565 (17)	0.0672 (18)	0.0454 (15)	−0.0129 (14)	0.0013 (13)	0.0010 (13)
C19	0.0560 (18)	0.072 (2)	0.068 (2)	−0.0215 (15)	−0.0003 (15)	−0.0026 (15)
C20	0.0497 (17)	0.0519 (16)	0.073 (2)	−0.0095 (13)	0.0081 (14)	0.0057 (14)
C21	0.0667 (19)	0.0624 (18)	0.0506 (16)	−0.0116 (15)	0.0165 (14)	0.0087 (14)
C22	0.0572 (17)	0.0512 (15)	0.0466 (15)	−0.0130 (13)	0.0014 (12)	0.0018 (12)
C23	0.078 (2)	0.094 (3)	0.106 (3)	−0.039 (2)	0.028 (2)	0.000 (2)
C24	0.146 (4)	0.114 (3)	0.137 (4)	−0.077 (3)	−0.020 (3)	0.051 (3)

Cl1—C1	1.729 (3)	C10—C11	1.384 (3)
Cl2—C3	1.720 (3)	C11—C12	1.360 (4)
N1—N2	1.356 (3)	C11—H11A	0.9300
N1—C10	1.358 (3)	C12—C13	1.393 (4)
N1—C9	1.438 (3)	C12—H12A	0.9300
N2—N3	1.298 (3)	C13—C14	1.354 (4)
N3—C15	1.379 (4)	C13—H13A	0.9300
O1—C7	1.194 (3)	C14—C15	1.399 (4)
O2—C7	1.349 (3)	C14—H14A	0.9300
O2—C8	1.432 (3)	C16—C17	1.479 (3)
O3—C16	1.213 (3)	C17—C18	1.384 (4)
C1—C6	1.368 (4)	C17—C22	1.388 (3)
C1—C2	1.366 (4)	C18—C19	1.368 (4)
C2—C3	1.376 (4)	C18—H18A	0.9300
C2—H2B	0.9300	C19—C20	1.372 (4)
C3—C4	1.389 (3)	C19—H19A	0.9300
C4—C5	1.378 (4)	C20—C21	1.376 (4)
C4—C7	1.482 (3)	C20—C23	1.506 (4)
C5—C6	1.365 (4)	C21—C22	1.378 (4)
C5—H5A	0.9300	C21—H21A	0.9300
C6—H6A	0.9300	C22—H22A	0.9300
C8—C9	1.511 (3)	C23—C24	1.471 (5)
C8—C16	1.517 (3)	C23—H23A	0.9700
C8—H8A	0.9800	C23—H23B	0.9700
C9—H9A	0.9700	C24—H24A	0.9600
C9—H9B	0.9700	C24—H24B	0.9600
C10—C15	1.379 (4)	C24—H24C	0.9600
?···?	?
N2—N1—C10	109.9 (2)	C11—C12—C13	122.3 (3)
N2—N1—C9	119.9 (2)	C11—C12—H12A	118.9
C10—N1—C9	130.1 (2)	C13—C12—H12A	118.9
N3—N2—N1	109.1 (2)	C14—C13—C12	121.5 (3)
N2—N3—C15	107.8 (2)	C14—C13—H13A	119.2
C7—O2—C8	114.28 (19)	C12—C13—H13A	119.2
C6—C1—C2	121.2 (3)	C13—C14—C15	117.6 (3)
C6—C1—Cl1	120.3 (2)	C13—C14—H14A	121.2
C2—C1—Cl1	118.4 (2)	C15—C14—H14A	121.2
C1—C2—C3	119.2 (2)	N3—C15—C10	108.8 (2)
C1—C2—H2B	120.4	N3—C15—C14	131.5 (3)
C3—C2—H2B	120.4	C10—C15—C14	119.7 (3)
C2—C3—C4	121.0 (2)	O3—C16—C17	121.2 (2)
C2—C3—Cl2	116.5 (2)	O3—C16—C8	119.3 (2)
C4—C3—Cl2	122.5 (2)	C17—C16—C8	119.5 (2)
C5—C4—C3	117.6 (2)	C18—C17—C22	117.9 (2)
C5—C4—C7	119.7 (2)	C18—C17—C16	118.7 (2)
C3—C4—C7	122.7 (2)	C22—C17—C16	123.4 (2)
C6—C5—C4	122.1 (2)	C19—C18—C17	121.2 (3)
C6—C5—H5A	119.0	C19—C18—H18A	119.4
C4—C5—H5A	119.0	C17—C18—H18A	119.4
C5—C6—C1	118.9 (3)	C18—C19—C20	121.3 (3)
C5—C6—H6A	120.6	C18—C19—H19A	119.3
C1—C6—H6A	120.6	C20—C19—H19A	119.3
O1—C7—O2	122.2 (2)	C19—C20—C21	117.6 (3)
O1—C7—C4	126.3 (2)	C19—C20—C23	120.6 (3)
O2—C7—C4	111.5 (2)	C21—C20—C23	121.7 (3)
O2—C8—C9	105.67 (19)	C22—C21—C20	122.0 (3)
O2—C8—C16	109.74 (19)	C22—C21—H21A	119.0
C9—C8—C16	111.0 (2)	C20—C21—H21A	119.0
O2—C8—H8A	110.1	C21—C22—C17	119.9 (3)
C9—C8—H8A	110.1	C21—C22—H22A	120.0
C16—C8—H8A	110.1	C17—C22—H22A	120.0
N1—C9—C8	112.2 (2)	C24—C23—C20	113.1 (3)
N1—C9—H9A	109.2	C24—C23—H23A	109.0
C8—C9—H9A	109.2	C20—C23—H23A	109.0
N1—C9—H9B	109.2	C24—C23—H23B	109.0
C8—C9—H9B	109.2	C20—C23—H23B	109.0
H9A—C9—H9B	107.9	H23A—C23—H23B	107.8
N1—C10—C15	104.4 (2)	C23—C24—H24A	109.5
N1—C10—C11	132.5 (2)	C23—C24—H24B	109.5
C15—C10—C11	123.0 (3)	H24A—C24—H24B	109.5
C12—C11—C10	115.9 (3)	C23—C24—H24C	109.5
C12—C11—H11A	122.1	H24A—C24—H24C	109.5
C10—C11—H11A	122.1	H24B—C24—H24C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11A···O3i	0.93	2.51	3.425 (3)	169
C12—H12A···O1ii	0.93	2.52	3.378 (4)	154

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C11—H11A⋯O3i	0.93	2.51	3.425 (3)	169
C12—H12A⋯O1ii	0.93	2.52	3.378 (4)	154

Symmetry codes: (i) ; (ii) .