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Acta Crystallogr Sect E Struct Rep Online. 2008 May 1; 64(Pt 5): o942.
Published online 2008 April 30. doi:  10.1107/S1600536808011951
PMCID: PMC2961193

2-(1H-1,2,3-Benzotriazol-1-yl)-1-(4-ethyl­benzo­yl)ethyl 2,4-dichloro­benzoate

Abstract

In the title mol­ecule, C24H19Cl2N3, 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 inter­molecular C—H(...)O inter­actions.

Related literature

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

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Object name is e-64-0o942-scheme1.jpg

Experimental

Crystal data

  • C24H19Cl2N3O3
  • M r = 468.32
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-0o942-efi1.jpg
  • 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 [triangle]) 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 [triangle]); cell refinement: SAINT (Bruker, 1997 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: PLATON (Spek, 2003 [triangle]); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

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

supplementary crystallographic information

Comment

1H-Benzotriazole and its derivatives are an important class of compounds because they exhibit a broad spectrum of pharmacological activities such as antifungal, antitumor and antineoplastic activities (Chen & Wu, 2005). All bond lengths and angles in the title molecule (I) are within normal ranges (Allen et al., 1987). The benzotriazole ring system is essentially planar, with a dihedral angle of 1.05 (1)° between the triazole ring (atoms N1—N3/C10/C16) and the benzene ring (C10—C16). The dihedral angles between the mean planes of the benzotriazole system and ring atoms C1—C6 and C17—C22 are 82.09 (1) and 16.53 (1), respectively. The dihedral angle between rings atoms C1—C6 and C17—C22 is 89.47 (2). In the crystal structure, weak intermolecular C—H···O hydrogen bonds (Table 1) link molecules into chains extended along the a axis.

Experimental

Bromine (3.2 g,0.02 mol) was added dropwise to a solution of 3-(1H-benzo[d][1,2,3]triazol-1-yl)-1-(4-ethylphenyl)propan-1-one (5.58 g,0.02 mol)and sodium acetate(1.6 g,0.02 mol) in acetic acid (50 ml). The reaction proceeded for 7 h. Water (50 ml) and chloroform (20 ml) were then added. The organic layer was washed successively with saturated sodium bicarbonate solution and brine, dried over anhydrous magnesium sulfate and the chloroform solution filtered. It was cooled with ice-water, and then an acetone solution (10 ml) of 2,4-dichlorobenzoic acid (3.8 g,0.02 mol) and tri ethylamine (2.8 ml) was added. The mixture was stirred with ice-water for about 6 h. The solution was then filtered and concentrated. Single crystals were obtained by slow evaporation of anacetone-ethylacetate(1:1 v/v) solution of (I) at room temperature over a period of one week.

Refinement

All H atoms were located in difference Fourier maps and constrained to ride on their parent atoms, with C—H distances in the range 0.93–0.97 Å, and with Uiso(H) = 1.2 Ueq(C) and 1.5 Ueq(methyl C) H atoms.

Figures

Fig. 1.
The molecular structure of (I), drawn with 30% probability ellipsoids.
Fig. 2.
Part of the crystal structure of (I) showing hydrogen bonds as dashed lines. Only H atoms involved in hydrogen bonds are shown.

Crystal data

C24H19Cl2N3O3Z = 2
Mr = 468.32F000 = 484
Triclinic, P1Dx = 1.407 Mg m3
Hall symbol: -P 1Mo Kα radiation λ = 0.71073 Å
a = 9.251 (3) ÅCell parameters from 3700 reflections
b = 10.904 (4) Åθ = 1.9–25.0º
c = 11.057 (4) ŵ = 0.33 mm1
α = 88.327 (6)ºT = 298 (2) K
β = 86.442 (6)ºBlock, colorless
γ = 83.304 (5)º0.20 × 0.20 × 0.10 mm
V = 1105.4 (6) Å3

Data collection

Bruker SMART CCD area-detector diffractometer3700 independent reflections
Radiation source: fine-focus sealed tube2701 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.016
T = 298(2) Kθmax = 25.0º
[var phi] and ω scansθmin = 1.9º
Absorption correction: multi-scan(SADABS; Bruker, 1997)h = −7→10
Tmin = 0.938, Tmax = 0.991k = −12→12
5375 measured reflectionsl = −10→12

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.046H-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 reflectionsΔρmax = 0.26 e Å3
289 parametersΔρmin = −0.34 e Å3
Primary atom site location: structure-invariant direct methodsExtinction correction: none

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 (Å2)

xyzUiso*/Ueq
Cl10.63408 (12)0.54323 (8)0.16704 (8)0.0986 (4)
Cl20.17075 (9)0.52373 (8)0.46851 (10)0.0910 (3)
N10.5431 (2)0.10230 (19)0.83967 (17)0.0471 (5)
N20.4769 (3)0.1341 (2)0.9489 (2)0.0609 (6)
N30.5560 (3)0.2042 (2)1.0028 (2)0.0672 (7)
O10.1957 (2)0.28033 (18)0.58441 (18)0.0651 (6)
O20.41844 (18)0.18987 (15)0.61852 (15)0.0468 (4)
O30.3025 (2)0.01135 (18)0.51586 (16)0.0608 (5)
C10.5439 (3)0.4634 (3)0.2799 (2)0.0596 (8)
C20.4102 (3)0.5146 (2)0.3249 (2)0.0577 (7)
H2B0.36850.58990.29420.069*
C30.3380 (3)0.4532 (2)0.4161 (2)0.0501 (6)
C40.4002 (3)0.3419 (2)0.4646 (2)0.0436 (6)
C50.5355 (3)0.2945 (2)0.4167 (2)0.0568 (7)
H5A0.57940.22040.44830.068*
C60.6073 (4)0.3530 (3)0.3245 (3)0.0694 (9)
H6A0.69770.31840.29240.083*
C70.3240 (3)0.2712 (2)0.5603 (2)0.0456 (6)
C80.3506 (3)0.1039 (2)0.6972 (2)0.0439 (6)
H8A0.28310.14830.75710.053*
C90.4734 (3)0.0290 (2)0.7597 (2)0.0482 (6)
H9A0.4352−0.03830.80590.058*
H9B0.5452−0.00650.69900.058*
C100.6686 (3)0.1556 (2)0.8221 (2)0.0431 (6)
C110.7727 (3)0.1540 (2)0.7266 (2)0.0503 (6)
H11A0.76640.10950.65700.060*
C120.8851 (3)0.2213 (3)0.7409 (3)0.0601 (8)
H12A0.95780.22280.67900.072*
C130.8951 (3)0.2882 (3)0.8449 (3)0.0700 (9)
H13A0.97380.33310.85040.084*
C140.7928 (4)0.2892 (3)0.9380 (3)0.0692 (8)
H14A0.79990.33401.00730.083*
C150.6762 (3)0.2204 (2)0.9264 (2)0.0538 (7)
C160.2697 (3)0.0221 (2)0.6232 (2)0.0431 (6)
C170.1553 (3)−0.0460 (2)0.6839 (2)0.0411 (6)
C180.0778 (3)−0.1156 (3)0.6140 (2)0.0562 (7)
H18A0.1012−0.12060.53110.067*
C19−0.0327 (3)−0.1769 (3)0.6645 (3)0.0643 (8)
H19A−0.0826−0.22330.61540.077*
C20−0.0714 (3)−0.1716 (3)0.7863 (3)0.0584 (7)
C210.0066 (3)−0.1038 (3)0.8564 (3)0.0606 (8)
H21A−0.0172−0.09970.93920.073*
C220.1188 (3)−0.0418 (2)0.8074 (2)0.0514 (7)
H22A0.16990.00290.85720.062*
C23−0.1960 (4)−0.2369 (3)0.8398 (4)0.0919 (12)
H23A−0.2398−0.19260.91020.110*
H23B−0.2696−0.23510.78080.110*
C24−0.1512 (5)−0.3659 (4)0.8759 (4)0.1279 (18)
H24A−0.2344−0.40240.91030.192*
H24B−0.0790−0.36840.93490.192*
H24C−0.1110−0.41120.80610.192*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Cl10.1231 (8)0.0765 (6)0.0850 (6)0.0018 (5)0.0436 (6)0.0298 (5)
Cl20.0503 (5)0.0744 (5)0.1377 (8)0.0148 (4)0.0167 (5)0.0406 (5)
N10.0510 (13)0.0529 (12)0.0360 (11)−0.0061 (10)0.0035 (10)0.0096 (9)
N20.0689 (16)0.0705 (16)0.0410 (13)−0.0087 (13)0.0113 (12)0.0072 (11)
N30.0821 (19)0.0766 (17)0.0422 (13)−0.0113 (15)0.0051 (13)0.0002 (12)
O10.0416 (12)0.0720 (13)0.0788 (14)−0.0037 (10)0.0036 (9)0.0222 (10)
O20.0430 (10)0.0462 (10)0.0507 (10)−0.0075 (8)−0.0010 (8)0.0142 (8)
O30.0685 (13)0.0705 (13)0.0441 (11)−0.0188 (10)0.0123 (9)−0.0010 (9)
C10.074 (2)0.0521 (16)0.0493 (16)−0.0051 (15)0.0089 (14)0.0100 (13)
C20.0620 (19)0.0476 (16)0.0618 (18)−0.0022 (14)−0.0054 (14)0.0154 (13)
C30.0428 (15)0.0477 (15)0.0590 (16)−0.0023 (12)−0.0059 (12)0.0075 (12)
C40.0450 (14)0.0429 (14)0.0434 (14)−0.0080 (11)−0.0032 (11)0.0038 (11)
C50.0624 (18)0.0464 (15)0.0559 (17)0.0070 (13)0.0107 (13)0.0119 (13)
C60.074 (2)0.0603 (18)0.0643 (19)0.0143 (16)0.0231 (16)0.0125 (15)
C70.0416 (15)0.0445 (14)0.0501 (15)−0.0042 (11)−0.0027 (12)0.0037 (12)
C80.0447 (15)0.0441 (14)0.0419 (13)−0.0077 (11)0.0042 (11)0.0090 (11)
C90.0530 (16)0.0463 (14)0.0451 (14)−0.0090 (12)0.0010 (12)0.0078 (11)
C100.0456 (15)0.0429 (13)0.0392 (13)−0.0006 (11)−0.0033 (11)0.0097 (11)
C110.0472 (16)0.0512 (15)0.0501 (16)−0.0002 (12)0.0030 (12)0.0073 (12)
C120.0459 (16)0.0578 (17)0.074 (2)−0.0024 (14)0.0039 (14)0.0090 (15)
C130.0560 (19)0.0633 (19)0.092 (2)−0.0130 (15)−0.0131 (18)0.0106 (18)
C140.083 (2)0.0620 (18)0.066 (2)−0.0107 (17)−0.0198 (18)−0.0055 (15)
C150.0627 (18)0.0527 (16)0.0453 (15)−0.0022 (14)−0.0088 (13)0.0043 (12)
C160.0414 (14)0.0424 (13)0.0429 (15)0.0001 (11)0.0055 (11)0.0058 (11)
C170.0401 (14)0.0385 (13)0.0428 (14)−0.0008 (11)0.0028 (11)0.0042 (11)
C180.0565 (17)0.0672 (18)0.0454 (15)−0.0129 (14)0.0013 (13)0.0010 (13)
C190.0560 (18)0.072 (2)0.068 (2)−0.0215 (15)−0.0003 (15)−0.0026 (15)
C200.0497 (17)0.0519 (16)0.073 (2)−0.0095 (13)0.0081 (14)0.0057 (14)
C210.0667 (19)0.0624 (18)0.0506 (16)−0.0116 (15)0.0165 (14)0.0087 (14)
C220.0572 (17)0.0512 (15)0.0466 (15)−0.0130 (13)0.0014 (12)0.0018 (12)
C230.078 (2)0.094 (3)0.106 (3)−0.039 (2)0.028 (2)0.000 (2)
C240.146 (4)0.114 (3)0.137 (4)−0.077 (3)−0.020 (3)0.051 (3)

Geometric parameters (Å, °)

Cl1—C11.729 (3)C10—C111.384 (3)
Cl2—C31.720 (3)C11—C121.360 (4)
N1—N21.356 (3)C11—H11A0.9300
N1—C101.358 (3)C12—C131.393 (4)
N1—C91.438 (3)C12—H12A0.9300
N2—N31.298 (3)C13—C141.354 (4)
N3—C151.379 (4)C13—H13A0.9300
O1—C71.194 (3)C14—C151.399 (4)
O2—C71.349 (3)C14—H14A0.9300
O2—C81.432 (3)C16—C171.479 (3)
O3—C161.213 (3)C17—C181.384 (4)
C1—C61.368 (4)C17—C221.388 (3)
C1—C21.366 (4)C18—C191.368 (4)
C2—C31.376 (4)C18—H18A0.9300
C2—H2B0.9300C19—C201.372 (4)
C3—C41.389 (3)C19—H19A0.9300
C4—C51.378 (4)C20—C211.376 (4)
C4—C71.482 (3)C20—C231.506 (4)
C5—C61.365 (4)C21—C221.378 (4)
C5—H5A0.9300C21—H21A0.9300
C6—H6A0.9300C22—H22A0.9300
C8—C91.511 (3)C23—C241.471 (5)
C8—C161.517 (3)C23—H23A0.9700
C8—H8A0.9800C23—H23B0.9700
C9—H9A0.9700C24—H24A0.9600
C9—H9B0.9700C24—H24B0.9600
C10—C151.379 (4)C24—H24C0.9600
?···??
N2—N1—C10109.9 (2)C11—C12—C13122.3 (3)
N2—N1—C9119.9 (2)C11—C12—H12A118.9
C10—N1—C9130.1 (2)C13—C12—H12A118.9
N3—N2—N1109.1 (2)C14—C13—C12121.5 (3)
N2—N3—C15107.8 (2)C14—C13—H13A119.2
C7—O2—C8114.28 (19)C12—C13—H13A119.2
C6—C1—C2121.2 (3)C13—C14—C15117.6 (3)
C6—C1—Cl1120.3 (2)C13—C14—H14A121.2
C2—C1—Cl1118.4 (2)C15—C14—H14A121.2
C1—C2—C3119.2 (2)N3—C15—C10108.8 (2)
C1—C2—H2B120.4N3—C15—C14131.5 (3)
C3—C2—H2B120.4C10—C15—C14119.7 (3)
C2—C3—C4121.0 (2)O3—C16—C17121.2 (2)
C2—C3—Cl2116.5 (2)O3—C16—C8119.3 (2)
C4—C3—Cl2122.5 (2)C17—C16—C8119.5 (2)
C5—C4—C3117.6 (2)C18—C17—C22117.9 (2)
C5—C4—C7119.7 (2)C18—C17—C16118.7 (2)
C3—C4—C7122.7 (2)C22—C17—C16123.4 (2)
C6—C5—C4122.1 (2)C19—C18—C17121.2 (3)
C6—C5—H5A119.0C19—C18—H18A119.4
C4—C5—H5A119.0C17—C18—H18A119.4
C5—C6—C1118.9 (3)C18—C19—C20121.3 (3)
C5—C6—H6A120.6C18—C19—H19A119.3
C1—C6—H6A120.6C20—C19—H19A119.3
O1—C7—O2122.2 (2)C19—C20—C21117.6 (3)
O1—C7—C4126.3 (2)C19—C20—C23120.6 (3)
O2—C7—C4111.5 (2)C21—C20—C23121.7 (3)
O2—C8—C9105.67 (19)C22—C21—C20122.0 (3)
O2—C8—C16109.74 (19)C22—C21—H21A119.0
C9—C8—C16111.0 (2)C20—C21—H21A119.0
O2—C8—H8A110.1C21—C22—C17119.9 (3)
C9—C8—H8A110.1C21—C22—H22A120.0
C16—C8—H8A110.1C17—C22—H22A120.0
N1—C9—C8112.2 (2)C24—C23—C20113.1 (3)
N1—C9—H9A109.2C24—C23—H23A109.0
C8—C9—H9A109.2C20—C23—H23A109.0
N1—C9—H9B109.2C24—C23—H23B109.0
C8—C9—H9B109.2C20—C23—H23B109.0
H9A—C9—H9B107.9H23A—C23—H23B107.8
N1—C10—C15104.4 (2)C23—C24—H24A109.5
N1—C10—C11132.5 (2)C23—C24—H24B109.5
C15—C10—C11123.0 (3)H24A—C24—H24B109.5
C12—C11—C10115.9 (3)C23—C24—H24C109.5
C12—C11—H11A122.1H24A—C24—H24C109.5
C10—C11—H11A122.1H24B—C24—H24C109.5

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C11—H11A···O3i0.932.513.425 (3)169
C12—H12A···O1ii0.932.523.378 (4)154

Symmetry codes: (i) −x+1, −y, −z+1; (ii) x+1, y, z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LH2614).

References

  • Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19.
  • Bruker (1997). SMART, SAINT and SADABS Bruker AXS Inc., Madison, Wisconsin, USA.
  • Chen, Z.-Y. & Wu, M.-J. (2005). Org. Lett.7, 475–477. [PubMed]
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Spek, A. L. (2003). J. Appl. Cryst.36, 7–13.

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography