organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

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

aCollege of Chemistry and Chemical Engineering, Guangxi University, 530004 Nanning, Guangxi, People's Republic of China, and bCollege of Chemistry and Molecular Engineering, Qingdao University of Science and Technology, 266042 Qingdao, Shandong, People's Republic of China
*Correspondence e-mail: qustchemistry@126.com

(Received 16 July 2008; accepted 23 July 2008; online 31 July 2008)

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 ππ [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[Bi, S., Luo, H., Zeng, W.-L. & Wan, J. (2007). Acta Cryst. E63, o4499.]); Allen et al. (1987[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.]).

[Scheme 1]

Experimental

Crystal data
  • C23H18ClN3O3

  • Mr = 419.85

  • Monoclinic, P 21 /c

  • 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[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.934, Tmax = 0.983

  • 11618 measured reflections

  • 4112 independent reflections

  • 2671 reflections with I > 2σ(I)

  • Rint = 0.032

Refinement
  • R[F2 > 2σ(F2)] = 0.058

  • wR(F2) = 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

Table 1
C—H⋯π interactions (Å, °)

Cg4 is the centroid of the tolyl ring.

  C—H C⋯Cg C—H⋯Cg H⋯Cg
C2—H2BCg4ii 0.93 3.879 (3) 168 2.96
Symmetry codes: (i) 2-x, 2-y, 2-z; (ii) [x-1, -y+{3 \over 2}, z-{1 \over 2}].

Data collection: SMART (Siemens, 1996[Siemens (1996). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Siemens, 1996[Siemens (1996). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995[Nardelli, M. (1995). J. Appl. Cryst. 28, 659.]) and PLATON (Spek, 2003[Spek, A. L. (2003). J. Appl. Cryst. 36, 7-13.]).

Supporting information


Comment top

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 ππ and weak C—H···π interactions involving the tolyl ring D (Table 1).

Related literature top

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

Experimental top

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 top

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.

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); 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 (Sheldrick, 2008), PARST (Nardelli, 1995) and PLATON (Spek, 2003).

Figures top
[Figure 1] 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.
2-(1H-Benzotriazol-1-yl)-1-(2-chlorobenzoyl)ethyl 4-methylbenzoate top
Crystal data top
C23H18ClN3O3F(000) = 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 = 2.6–21.5°
b = 26.151 (2) ŵ = 0.21 mm1
c = 10.6002 (9) ÅT = 293 K
β = 107.895 (1)°Plate, colourless
V = 2090.7 (3) Å30.31 × 0.17 × 0.07 mm
Z = 4
Data collection top
Siemens SMART 1000 CCD area-detector
diffractometer
4112 independent reflections
Radiation source: fine-focus sealed tube2671 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.032
Detector resolution: 8.33 pixels mm-1θmax = 26.0°, θmin = 2.2°
ω scansh = 79
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
k = 3132
Tmin = 0.934, Tmax = 0.983l = 1311
11618 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.058Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.155H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.0736P)2 + 0.3577P]
where P = (Fo2 + 2Fc2)/3
4112 reflections(Δ/σ)max = 0.001
271 parametersΔρmax = 0.35 e Å3
0 restraintsΔρmin = 0.14 e Å3
Crystal data top
C23H18ClN3O3V = 2090.7 (3) Å3
Mr = 419.85Z = 4
Monoclinic, P21/cMo Kα radiation
a = 7.9254 (7) ŵ = 0.21 mm1
b = 26.151 (2) ÅT = 293 K
c = 10.6002 (9) Å0.31 × 0.17 × 0.07 mm
β = 107.895 (1)°
Data collection top
Siemens SMART 1000 CCD area-detector
diffractometer
4112 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
2671 reflections with I > 2σ(I)
Tmin = 0.934, Tmax = 0.983Rint = 0.032
11618 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0580 restraints
wR(F2) = 0.155H-atom parameters constrained
S = 1.02Δρmax = 0.35 e Å3
4112 reflectionsΔρmin = 0.14 e Å3
271 parameters
Special details top

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) top
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)
H4B0.03790.77620.93380.106*
C30.0112 (5)0.71282 (17)0.8449 (4)0.1012 (13)
H3B0.09940.69800.83250.121*
Atomic displacement parameters (Å2) top
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, º) top
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—C17177.87 (19)C9—C8—C7—C674.3 (3)
N2—N1—C10—C110.5 (3)N2—N1—C9—C874.9 (3)
C9—N1—C10—C11170.9 (2)C10—N1—C9—C894.6 (3)
N2—N1—C10—C15179.8 (3)O2—C8—C9—N153.5 (3)
C9—N1—C10—C159.4 (4)C7—C8—C9—N1174.0 (2)
N1—C10—C11—N30.2 (3)C1—C6—C5—C40.1 (4)
C15—C10—C11—N3179.9 (2)C7—C6—C5—C4177.9 (2)
N1—C10—C11—C12179.9 (2)C5—C6—C1—C21.0 (4)
C15—C10—C11—C120.4 (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—Cl13.4 (3)
O3—C16—C17—C184.8 (4)C10—C15—C14—C130.3 (4)
O2—C16—C17—C18176.0 (2)C6—C1—C2—C31.6 (5)
O3—C16—C17—C22175.4 (3)Cl1—C1—C2—C3179.5 (2)
O2—C16—C17—C223.8 (3)C22—C17—C18—C190.9 (4)
N1—N2—N3—C110.4 (3)C16—C17—C18—C19178.9 (2)
C10—C11—N3—N20.1 (3)N3—C11—C12—C13179.2 (3)
C12—C11—N3—N2179.5 (3)C10—C11—C12—C130.4 (4)
C16—O2—C8—C776.5 (2)C11—C12—C13—C140.8 (4)
C16—O2—C8—C9164.1 (2)C15—C14—C13—C120.5 (5)
C18—C17—C22—C210.2 (4)C21—C20—C19—C180.3 (4)
C16—C17—C22—C21179.6 (2)C23—C20—C19—C18179.7 (3)
N1—C10—C15—C14179.6 (2)C17—C18—C19—C200.6 (4)
C11—C10—C15—C140.7 (4)C19—C20—C21—C220.9 (4)
C1—C6—C7—O166.6 (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—C30.2 (5)
C5—C6—C7—C870.2 (3)C5—C4—C3—C20.3 (5)
O2—C8—C7—O112.9 (3)C1—C2—C3—C41.2 (5)
C9—C8—C7—O1104.5 (3)

Experimental details

Crystal data
Chemical formulaC23H18ClN3O3
Mr419.85
Crystal system, space groupMonoclinic, P21/c
Temperature (K)293
a, b, c (Å)7.9254 (7), 26.151 (2), 10.6002 (9)
β (°) 107.895 (1)
V3)2090.7 (3)
Z4
Radiation typeMo Kα
µ (mm1)0.21
Crystal size (mm)0.31 × 0.17 × 0.07
Data collection
DiffractometerSiemens SMART 1000 CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.934, 0.983
No. of measured, independent and
observed [I > 2σ(I)] reflections
11618, 4112, 2671
Rint0.032
(sin θ/λ)max1)0.618
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.058, 0.155, 1.02
No. of reflections4112
No. of parameters271
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.35, 0.14

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008), PARST (Nardelli, 1995) and PLATON (Spek, 2003).

ππ and C—H···π interactions top
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
 

Acknowledgements

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

References

First citationAllen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19.  CrossRef Web of Science Google Scholar
First citationBi, S., Luo, H., Zeng, W.-L. & Wan, J. (2007). Acta Cryst. E63, o4499.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationNardelli, M. (1995). J. Appl. Cryst. 28, 659.  CrossRef IUCr Journals Google Scholar
First citationSheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSiemens (1996). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.  Google Scholar
First citationSpek, A. L. (2003). J. Appl. Cryst. 36, 7–13.  Web of Science CrossRef CAS IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds