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Acta Crystallogr Sect E Struct Rep Online. 2008 August 1; 64(Pt 8): o1619.
Published online 2008 July 31. doi:  10.1107/S1600536808023222
PMCID: PMC2962228

2-(1H-Benzotriazol-1-yl)-1-(2-chloro­benzo­yl)ethyl 4-methyl­benzoate

Abstract

In the mol­ecule of the title compound, C23H18ClN3O3, the essentially planar benzotriazole ring makes dihedral angles of 52.93 (1) and 85.21 (1)°, respectively, with the chloro­phenyl and tolyl rings. The crystal packing is stabilized by π–π [centroid-to-centroid distance 3.830 (2) Å, interplanar distance 3.705 Å, slippage 0.968 Å]; C—H(...)π(...)tolyl ring inter­actions are also present.

Related literature

For related literature, see: Bi et al., (2007 [triangle]); Allen et al. (1987 [triangle]).

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Object name is e-64-o1619-scheme1.jpg

Experimental

Crystal data

  • C23H18ClN3O3
  • M r = 419.85
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-o1619-efi1.jpg
  • a = 7.9254 (7) Å
  • b = 26.151 (2) Å
  • c = 10.6002 (9) Å
  • β = 107.895 (1)°
  • V = 2090.7 (3) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.21 mm−1
  • T = 293 (2) K
  • 0.31 × 0.17 × 0.07 mm

Data collection

  • Siemens SMART 1000 CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.934, T max = 0.983
  • 11618 measured reflections
  • 4112 independent reflections
  • 2671 reflections with I > 2σ(I)
  • R int = 0.032

Refinement

  • R[F 2 > 2σ(F 2)] = 0.058
  • wR(F 2) = 0.155
  • S = 1.02
  • 4112 reflections
  • 271 parameters
  • H-atom parameters constrained
  • Δρmax = 0.35 e Å−3
  • Δρmin = −0.14 e Å−3

Data collection: SMART (Siemens, 1996 [triangle]); cell refinement: SAINT (Siemens, 1996 [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: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995 [triangle]) and PLATON (Spek, 2003 [triangle]).

Table 1
C—H(...)π interactions (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808023222/dn2368sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808023222/dn2368Isup2.hkl

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

Acknowledgments

This project was supported by the Natural Science Foundation of Shandong Province (grant No. Y2006B07).

supplementary crystallographic information

Comment

Recently we have reported the structure of 2-(1H-benzotriazol-1-yl)-1-(2-fluorobenzoyl)ethyl benzoate (II) (Bi et al., 2007). As part of our ongoing studies on benzotriazole derivatives with higher pharmacological activities, the title compound (I) was synthesized and its structure is shown here.

In (I), all bond lengths and angles are within normal ranges (Allen et al., 1987) and are comparable with those in the related compound (II). In (I), the benzotriazole moiety is essentially planar with a dihedral angle of 0.46 (1)° between the N1–N3/C10/C11 triazole ring (A) and C10–C15 phenyl ring (B). The whole molecular is non-planar (Fig. 1). The benzotriazole system makes dihedral angles of 52.93 (1)° and 85.21 (1)° with the chlorophenyl C1–C6 (C) and the tolyl C17–C22 (D) rings respectively. The dihedral between the two phenyl rings, viz. C and D, is 34.40 (1)°.

The crystal packing is stabilized by slippest π–π and weak C—H···π interactions involving the tolyl ring D (Table 1).

Experimental

The title compound was prepared according to the literature method of Bi et al. (2007). Single crystals suitable for X-ray diffraction were obtained by slow evaporation of an ethyl acetate solution at room temperature over a period of 6 d.

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) H atoms and 1.5 Ueq(methyl C) H atoms.

Figures

Fig. 1.
Molecular structure of compound (I) with the atom-labelling scheme. Ellipsoids are drawn at the 50% probability level. H atoms are represented as small spheres of arbitrary radii.

Crystal data

C23H18ClN3O3F000 = 872
Mr = 419.85Dx = 1.334 Mg m3
Monoclinic, P21/cMo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 2285 reflections
a = 7.9254 (7) Åθ = 2.6–21.5º
b = 26.151 (2) ŵ = 0.21 mm1
c = 10.6002 (9) ÅT = 293 (2) K
β = 107.8950 (10)ºPlate, colourless
V = 2090.7 (3) Å30.31 × 0.17 × 0.07 mm
Z = 4

Data collection

Siemens SMART 1000 CCD area-detector diffractometer4112 independent reflections
Radiation source: fine-focus sealed tube2671 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.032
Detector resolution: 8.33 pixels mm-1θmax = 26.0º
T = 293(2) Kθmin = 2.2º
ω scansh = −7→9
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)k = −31→32
Tmin = 0.934, Tmax = 0.983l = −13→11
11618 measured reflections

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.058H-atom parameters constrained
wR(F2) = 0.155  w = 1/[σ2(Fo2) + (0.0736P)2 + 0.3577P] where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max = 0.001
4112 reflectionsΔρmax = 0.35 e Å3
271 parametersΔρmin = −0.14 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
Cl10.45657 (13)0.67700 (3)0.76685 (8)0.0850 (3)
O20.6915 (2)0.85387 (6)0.88074 (15)0.0519 (4)
N10.5321 (3)0.85694 (8)0.61201 (19)0.0494 (5)
C160.7125 (3)0.88114 (9)0.9930 (2)0.0521 (6)
O10.6508 (2)0.76281 (7)0.9880 (2)0.0724 (6)
C100.6819 (3)0.87350 (9)0.5879 (2)0.0447 (6)
C60.3402 (3)0.75625 (9)0.8833 (2)0.0483 (6)
O30.6005 (3)0.88270 (8)1.0475 (2)0.0811 (6)
C110.6356 (3)0.92094 (10)0.5281 (2)0.0518 (6)
N20.4019 (3)0.89243 (9)0.5702 (2)0.0627 (6)
C170.8850 (3)0.90815 (9)1.0357 (2)0.0501 (6)
N30.4614 (3)0.93082 (9)0.5193 (2)0.0679 (6)
C80.5253 (3)0.82806 (9)0.8302 (2)0.0479 (6)
H8A0.42850.85110.83160.058*
C221.0019 (3)0.90722 (10)0.9622 (3)0.0606 (7)
H22A0.97310.88940.88250.073*
C150.8502 (3)0.85257 (11)0.6109 (3)0.0576 (7)
H15A0.88050.82070.65010.069*
C70.5192 (3)0.78034 (9)0.9101 (2)0.0493 (6)
C90.5084 (3)0.81338 (10)0.6880 (2)0.0537 (6)
H9A0.59670.78770.68810.064*
H9B0.39230.79860.64670.064*
C201.2093 (4)0.95912 (10)1.1248 (3)0.0649 (8)
C50.2118 (4)0.78141 (11)0.9250 (3)0.0644 (7)
H5A0.23690.81320.96590.077*
C10.3004 (4)0.70910 (10)0.8229 (3)0.0597 (7)
C140.9684 (4)0.88207 (12)0.5720 (3)0.0689 (8)
H14A1.08270.86980.58570.083*
C20.1361 (5)0.68742 (13)0.8019 (3)0.0889 (11)
H2B0.10930.65600.75910.107*
C180.9309 (4)0.93510 (11)1.1532 (3)0.0678 (8)
H18A0.85300.93651.20320.081*
C120.7585 (4)0.94992 (11)0.4889 (3)0.0681 (8)
H12A0.72900.98160.44830.082*
C130.9234 (4)0.92969 (12)0.5129 (3)0.0703 (8)
H13A1.00880.94830.48900.084*
C191.0918 (4)0.95997 (11)1.1968 (3)0.0745 (9)
H19A1.12140.97771.27660.089*
C211.1613 (4)0.93279 (11)1.0071 (3)0.0698 (8)
H21A1.23830.93220.95630.084*
C231.3858 (4)0.98627 (13)1.1738 (3)0.0903 (11)
H23A1.45130.98091.11240.135*
H23B1.45190.97301.25910.135*
H23C1.36631.02221.18120.135*
C40.0476 (4)0.75943 (16)0.9057 (4)0.0883 (11)
H4B−0.03790.77620.93380.106*
C30.0112 (5)0.71282 (17)0.8449 (4)0.1012 (13)
H3B−0.09940.69800.83250.121*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Cl10.1093 (7)0.0709 (5)0.0759 (5)0.0079 (4)0.0300 (5)−0.0074 (4)
O20.0451 (10)0.0619 (11)0.0536 (10)−0.0130 (8)0.0225 (8)−0.0098 (8)
N10.0367 (11)0.0624 (13)0.0496 (11)−0.0072 (10)0.0142 (9)0.0039 (10)
C160.0540 (16)0.0540 (15)0.0527 (15)−0.0025 (12)0.0228 (13)−0.0039 (12)
O10.0438 (11)0.0846 (14)0.0856 (14)0.0002 (10)0.0152 (10)0.0217 (11)
C100.0345 (13)0.0591 (15)0.0419 (12)−0.0108 (11)0.0137 (10)−0.0052 (11)
C60.0427 (14)0.0576 (15)0.0465 (13)−0.0047 (11)0.0165 (11)0.0085 (11)
O30.0696 (14)0.1081 (16)0.0804 (14)−0.0179 (12)0.0449 (12)−0.0298 (12)
C110.0471 (16)0.0581 (16)0.0501 (14)−0.0084 (12)0.0149 (12)−0.0014 (11)
N20.0390 (12)0.0761 (16)0.0724 (15)−0.0028 (11)0.0163 (11)0.0049 (12)
C170.0545 (16)0.0477 (13)0.0482 (14)−0.0009 (11)0.0158 (12)−0.0027 (11)
N30.0504 (15)0.0699 (15)0.0814 (16)0.0030 (11)0.0174 (12)0.0120 (12)
C80.0378 (13)0.0547 (15)0.0548 (14)−0.0090 (11)0.0194 (11)−0.0034 (11)
C220.0516 (16)0.0700 (17)0.0598 (16)−0.0093 (13)0.0164 (13)−0.0141 (13)
C150.0457 (16)0.0662 (17)0.0640 (16)−0.0009 (12)0.0215 (13)−0.0002 (13)
C70.0443 (15)0.0570 (15)0.0518 (14)−0.0008 (12)0.0225 (12)−0.0018 (12)
C90.0494 (15)0.0618 (16)0.0532 (14)−0.0150 (12)0.0206 (12)−0.0043 (12)
C200.0551 (17)0.0583 (17)0.0679 (18)−0.0077 (13)−0.0008 (14)0.0008 (14)
C50.0508 (17)0.0745 (18)0.0741 (18)0.0048 (14)0.0283 (14)0.0126 (15)
C10.0618 (18)0.0566 (16)0.0583 (16)−0.0050 (13)0.0150 (13)0.0094 (13)
C140.0421 (15)0.092 (2)0.079 (2)−0.0107 (15)0.0283 (14)−0.0150 (17)
C20.078 (3)0.077 (2)0.095 (2)−0.0308 (19)0.002 (2)0.0156 (18)
C180.072 (2)0.0725 (19)0.0608 (17)−0.0042 (15)0.0226 (15)−0.0104 (14)
C120.069 (2)0.0677 (18)0.0687 (18)−0.0202 (15)0.0221 (15)0.0041 (14)
C130.064 (2)0.085 (2)0.0726 (19)−0.0302 (17)0.0367 (16)−0.0098 (16)
C190.079 (2)0.075 (2)0.0608 (18)−0.0149 (16)0.0086 (16)−0.0176 (15)
C210.0545 (17)0.080 (2)0.077 (2)−0.0132 (15)0.0236 (15)−0.0113 (16)
C230.065 (2)0.090 (2)0.099 (2)−0.0200 (17)−0.0015 (17)−0.0090 (19)
C40.0479 (19)0.112 (3)0.112 (3)0.0068 (19)0.0347 (18)0.038 (2)
C30.048 (2)0.116 (3)0.130 (3)−0.026 (2)0.015 (2)0.047 (3)

Geometric parameters (Å, °)

Cl1—C11.744 (3)C9—H9A0.9700
O2—C161.353 (3)C9—H9B0.9700
O2—C81.429 (3)C20—C211.372 (4)
N1—N21.357 (3)C20—C191.374 (4)
N1—C101.360 (3)C20—C231.512 (4)
N1—C91.441 (3)C5—C41.379 (4)
C16—O31.200 (3)C5—H5A0.9300
C16—C171.480 (3)C1—C21.374 (4)
O1—C71.204 (3)C14—C131.391 (4)
C10—C111.390 (3)C14—H14A0.9300
C10—C151.392 (3)C2—C31.381 (5)
C6—C11.381 (4)C2—H2B0.9300
C6—C51.392 (4)C18—C191.378 (4)
C6—C71.498 (3)C18—H18A0.9300
C11—N31.380 (3)C12—C131.359 (4)
C11—C121.394 (4)C12—H12A0.9300
N2—N31.296 (3)C13—H13A0.9300
C17—C181.379 (4)C19—H19A0.9300
C17—C221.382 (3)C21—H21A0.9300
C8—C71.517 (3)C23—H23A0.9600
C8—C91.521 (3)C23—H23B0.9600
C8—H8A0.9800C23—H23C0.9600
C22—C211.378 (4)C4—C31.367 (5)
C22—H22A0.9300C4—H4B0.9300
C15—C141.371 (4)C3—H3B0.9300
C15—H15A0.9300
C16—O2—C8115.37 (18)C21—C20—C19117.8 (3)
N2—N1—C10109.96 (19)C21—C20—C23121.2 (3)
N2—N1—C9120.5 (2)C19—C20—C23121.0 (3)
C10—N1—C9128.9 (2)C4—C5—C6120.3 (3)
O3—C16—O2122.2 (2)C4—C5—H5A119.9
O3—C16—C17125.9 (2)C6—C5—H5A119.9
O2—C16—C17111.9 (2)C2—C1—C6120.9 (3)
N1—C10—C11104.3 (2)C2—C1—Cl1118.9 (3)
N1—C10—C15133.4 (2)C6—C1—Cl1120.2 (2)
C11—C10—C15122.3 (2)C15—C14—C13122.3 (3)
C1—C6—C5119.0 (2)C15—C14—H14A118.8
C1—C6—C7122.1 (2)C13—C14—H14A118.8
C5—C6—C7118.9 (2)C1—C2—C3119.2 (3)
N3—C11—C10108.4 (2)C1—C2—H2B120.4
N3—C11—C12130.9 (3)C3—C2—H2B120.4
C10—C11—C12120.7 (2)C19—C18—C17120.3 (3)
N3—N2—N1109.2 (2)C19—C18—H18A119.9
C18—C17—C22118.8 (3)C17—C18—H18A119.9
C18—C17—C16118.9 (2)C13—C12—C11116.9 (3)
C22—C17—C16122.3 (2)C13—C12—H12A121.6
N2—N3—C11108.2 (2)C11—C12—H12A121.6
O2—C8—C7111.28 (19)C12—C13—C14122.1 (3)
O2—C8—C9106.32 (18)C12—C13—H13A118.9
C7—C8—C9109.72 (19)C14—C13—H13A118.9
O2—C8—H8A109.8C20—C19—C18121.4 (3)
C7—C8—H8A109.8C20—C19—H19A119.3
C9—C8—H8A109.8C18—C19—H19A119.3
C21—C22—C17119.9 (3)C20—C21—C22121.8 (3)
C21—C22—H22A120.0C20—C21—H21A119.1
C17—C22—H22A120.0C22—C21—H21A119.1
C14—C15—C10115.6 (3)C20—C23—H23A109.5
C14—C15—H15A122.2C20—C23—H23B109.5
C10—C15—H15A122.2H23A—C23—H23B109.5
O1—C7—C6122.7 (2)C20—C23—H23C109.5
O1—C7—C8121.8 (2)H23A—C23—H23C109.5
C6—C7—C8115.5 (2)H23B—C23—H23C109.5
N1—C9—C8111.6 (2)C3—C4—C5119.6 (3)
N1—C9—H9A109.3C3—C4—H4B120.2
C8—C9—H9A109.3C5—C4—H4B120.2
N1—C9—H9B109.3C4—C3—C2121.0 (3)
C8—C9—H9B109.3C4—C3—H3B119.5
H9A—C9—H9B108.0C2—C3—H3B119.5
C8—O2—C16—O31.4 (3)O2—C8—C7—C6168.29 (19)
C8—O2—C16—C17−177.87 (19)C9—C8—C7—C6−74.3 (3)
N2—N1—C10—C11−0.5 (3)N2—N1—C9—C8−74.9 (3)
C9—N1—C10—C11−170.9 (2)C10—N1—C9—C894.6 (3)
N2—N1—C10—C15179.8 (3)O2—C8—C9—N1−53.5 (3)
C9—N1—C10—C159.4 (4)C7—C8—C9—N1−174.0 (2)
N1—C10—C11—N30.2 (3)C1—C6—C5—C4−0.1 (4)
C15—C10—C11—N3179.9 (2)C7—C6—C5—C4−177.9 (2)
N1—C10—C11—C12179.9 (2)C5—C6—C1—C21.0 (4)
C15—C10—C11—C12−0.4 (4)C7—C6—C1—C2178.7 (2)
C10—N1—N2—N30.6 (3)C5—C6—C1—Cl1178.87 (19)
C9—N1—N2—N3171.9 (2)C7—C6—C1—Cl1−3.4 (3)
O3—C16—C17—C184.8 (4)C10—C15—C14—C13−0.3 (4)
O2—C16—C17—C18−176.0 (2)C6—C1—C2—C3−1.6 (5)
O3—C16—C17—C22−175.4 (3)Cl1—C1—C2—C3−179.5 (2)
O2—C16—C17—C223.8 (3)C22—C17—C18—C19−0.9 (4)
N1—N2—N3—C11−0.4 (3)C16—C17—C18—C19178.9 (2)
C10—C11—N3—N20.1 (3)N3—C11—C12—C13179.2 (3)
C12—C11—N3—N2−179.5 (3)C10—C11—C12—C13−0.4 (4)
C16—O2—C8—C7−76.5 (2)C11—C12—C13—C140.8 (4)
C16—O2—C8—C9164.1 (2)C15—C14—C13—C12−0.5 (5)
C18—C17—C22—C210.2 (4)C21—C20—C19—C180.3 (4)
C16—C17—C22—C21−179.6 (2)C23—C20—C19—C18−179.7 (3)
N1—C10—C15—C14−179.6 (2)C17—C18—C19—C200.6 (4)
C11—C10—C15—C140.7 (4)C19—C20—C21—C22−0.9 (4)
C1—C6—C7—O1−66.6 (3)C23—C20—C21—C22179.0 (3)
C5—C6—C7—O1111.1 (3)C17—C22—C21—C200.7 (4)
C1—C6—C7—C8112.1 (3)C6—C5—C4—C3−0.2 (5)
C5—C6—C7—C8−70.2 (3)C5—C4—C3—C2−0.3 (5)
O2—C8—C7—O1−12.9 (3)C1—C2—C3—C41.2 (5)
C9—C8—C7—O1104.5 (3)

Table 1 π–π and C—H···π interactions

Cg4 is the centroid of the tolyl ring. Symmetry codes: (i) 2-x, 2-y, 2-z; (ii) x-1, -y+3/2, z-1/2.

Centroid–centroid (Å)Interplanar distance (Å)Slippage (Å)
Cg4···Cg4i3.830 (2)3.7050.968
C···Cg (Å)C—H···Cg (°)H···Cg (Å)
C2···Cg4ii3.879 (3)1682.96

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: DN2368).

References

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