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ADDENDA AND ERRATA

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2-(1H-Benzotriazol-1-yl)-1-(3-bromo­benzo­yl)ethyl benzoate

aCollege of Life Science and Pharmaceutical Engineering, Nanjing University of Technology, 210009 Nanjing, Jiangsu, People's Republic of China
*Correspondence e-mail: wangwei9612@126.com

(Received 13 January 2009; accepted 21 January 2009; online 28 January 2009)

In the title compound, C22H16BrN3O3, the dihedral angles between the benzotriazole mean plane and the benzene rings of 4.84 (1) and 89.50 (1)°. The dihedral angle between the two benzene rings is 84.77 (1)°. In the crystal structure, mol­ecules are linked into chains by inter­molecular C—H⋯O hydrogen bonds. The crystal packing is further stabilized by C—H⋯π inter­actions.

Related literature

For general background on benzotriazoles, see: Xu et al. (2003[Xu, L. Z., Zhang, S. S. & Hu, Z. Q. (2003). Chem. Res. Chin. Univ. 19, 310-313.]). For the synthesis, see: Zhang et al. (2006[Zhang, S.-S., Wan, J., Peng, Z.-Z. & Bi, S. (2006). Acta Cryst. E62, o4348-o4349.]). For bond-length data, see: 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
  • C22H16BrN3O3

  • Mr = 450.28

  • Triclinic, [P \overline 1]

  • a = 6.4390 (12) Å

  • b = 8.8267 (17) Å

  • c = 17.430 (3) Å

  • α = 88.589 (3)°

  • β = 85.024 (3)°

  • γ = 83.087 (3)°

  • V = 979.6 (3) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 2.13 mm−1

  • T = 293 (2) K

  • 0.42 × 0.12 × 0.10 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 = 0.469, Tmax = 0.815

  • 5526 measured reflections

  • 3773 independent reflections

  • 2885 reflections with I > 2σ(I)

  • Rint = 0.015

Refinement
  • R[F2 > 2σ(F2)] = 0.040

  • wR(F2) = 0.101

  • S = 1.04

  • 3773 reflections

  • 262 parameters

  • H-atom parameters constrained

  • Δρmax = 0.45 e Å−3

  • Δρmin = −0.33 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the N1–N3/C17/C18 ring.

D—H⋯A D—H H⋯A DA D—H⋯A
C16—H16ACg1i 0.93 2.78 3.571 144
C21—H21A⋯O3ii 0.93 2.47 3.202 (4) 136
Symmetry codes: (i) x+1, y, z; (ii) x, y+1, z.

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

Benzotriazole derivatives have become the most efficient antifungal compounds with the properties of low toxicity, high oral bioavailability and so on (Xu et al., 2003). In order to search for new benzotriazole compounds with higher bioactivity, the title compound, (I), was synthesized, and its structure is presented here.

In the title compound (I) (Fig. 1), all bond lengths and angles are within normal ranges (Allen et al., 1987). The benzotriazole ring is essentially planar with a dihedral angle of 0.29 (15)°. The whole molecule is non-planar, with the dihedral angles between the benzotriazole mean plane and C1–C6 and C11–C16 benzene rings of 4.84 (1) and 89.50 (1)°, respectively. The dihedral angle between the two benzene rings is 84.77 (1)°.

In the crystal structure (Fig. 2), molecules are linked into chains along b axis by C21—H21A···O3 intermolecular hydrogen bonds (Table 1). Furthermore, the crystal packing is further stabilized by C—H···π interactions (Table 1).

Related literature top

For general background on benzotriazoles, see: Xu et al., (2003). For synthesis, see: Zhang et al. (2006). For bond-length data, see: Allen et al. (1987). [Please check rephrasing]

Experimental top

The title compound was prepared according to the literature method of Zhang et al. (2006). Single crystals suitable for X-ray diffraction were obtained by slow evaporation of an ethyl acetate solution at room temperature over a period of six days.

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 0.93–0.978 Å, and with Uiso(H) = 1.2 Ueq(C).

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. The structure of the compound (I) showing 50% probability displacement ellipsoids and the atom numbering scheme.
[Figure 2] Fig. 2. A packing diagram of (I), viewed down the a axis. Hydrogen bonds are indicated by dashed lines.
2-(1H-Benzotriazol-1-yl)-1-(3-bromobenzoyl)ethyl benzoate top
Crystal data top
C22H16BrN3O3Z = 2
Mr = 450.28F(000) = 456
Triclinic, P1Dx = 1.527 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 6.4390 (12) ÅCell parameters from 2027 reflections
b = 8.8267 (17) Åθ = 2.3–24.1°
c = 17.430 (3) ŵ = 2.13 mm1
α = 88.589 (3)°T = 293 K
β = 85.024 (3)°Column, colourless
γ = 83.087 (3)°0.42 × 0.12 × 0.10 mm
V = 979.6 (3) Å3
Data collection top
Siemens SMART 1000 CCD area-detector
diffractometer
3773 independent reflections
Radiation source: fine-focus sealed tube2885 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.015
Detector resolution: 8.33 pixels mm-1θmax = 26.0°, θmin = 2.3°
ω scansh = 57
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
k = 810
Tmin = 0.469, Tmax = 0.815l = 2121
5526 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)] = 0.040Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.101H-atom parameters constrained
S = 1.04 w = 1/[σ2(Fo2) + (0.0529P)2 + 0.1162P]
where P = (Fo2 + 2Fc2)/3
3773 reflections(Δ/σ)max < 0.001
262 parametersΔρmax = 0.45 e Å3
0 restraintsΔρmin = 0.33 e Å3
Crystal data top
C22H16BrN3O3γ = 83.087 (3)°
Mr = 450.28V = 979.6 (3) Å3
Triclinic, P1Z = 2
a = 6.4390 (12) ÅMo Kα radiation
b = 8.8267 (17) ŵ = 2.13 mm1
c = 17.430 (3) ÅT = 293 K
α = 88.589 (3)°0.42 × 0.12 × 0.10 mm
β = 85.024 (3)°
Data collection top
Siemens SMART 1000 CCD area-detector
diffractometer
3773 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
2885 reflections with I > 2σ(I)
Tmin = 0.469, Tmax = 0.815Rint = 0.015
5526 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0400 restraints
wR(F2) = 0.101H-atom parameters constrained
S = 1.04Δρmax = 0.45 e Å3
3773 reflectionsΔρmin = 0.33 e Å3
262 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
Br10.15134 (5)0.67410 (4)0.013609 (18)0.07266 (15)
O10.8295 (3)1.1006 (2)0.19239 (12)0.0665 (5)
O20.6637 (3)1.31723 (18)0.28399 (10)0.0539 (5)
N20.0957 (4)1.4833 (3)0.16528 (13)0.0589 (6)
N10.2970 (3)1.4981 (2)0.19112 (12)0.0493 (5)
C30.2999 (4)0.8086 (3)0.04996 (15)0.0516 (6)
O30.6428 (4)1.1121 (2)0.35433 (12)0.0761 (6)
C170.3044 (4)1.6208 (3)0.23960 (14)0.0471 (6)
C70.6396 (4)1.1190 (3)0.18590 (15)0.0490 (6)
C40.5140 (4)0.7794 (3)0.06486 (15)0.0557 (7)
H4A0.58620.69150.04510.067*
C60.5140 (4)1.0130 (3)0.13989 (14)0.0471 (6)
C80.5243 (4)1.2583 (3)0.22507 (15)0.0499 (6)
H8A0.39931.23050.24700.060*
C20.1912 (4)0.9376 (3)0.08071 (16)0.0582 (7)
H2B0.04610.95620.07100.070*
C100.7238 (4)1.2242 (3)0.34460 (15)0.0544 (7)
C50.6206 (4)0.8806 (3)0.10897 (15)0.0535 (6)
H5A0.76560.86120.11850.064*
C180.0959 (4)1.6813 (3)0.24132 (15)0.0511 (6)
N30.0275 (4)1.5931 (3)0.19522 (14)0.0624 (6)
C10.2975 (4)1.0380 (3)0.12556 (16)0.0560 (7)
H1A0.22351.12380.14660.067*
C90.4638 (4)1.3866 (3)0.16730 (15)0.0541 (6)
H9A0.41941.34300.11780.065*
H9B0.58631.43760.16080.065*
C220.4686 (5)1.6847 (3)0.28088 (18)0.0610 (7)
H22A0.60801.64320.27930.073*
C110.9024 (4)1.2743 (3)0.39390 (15)0.0535 (6)
C210.4115 (5)1.8121 (3)0.3239 (2)0.0726 (9)
H21A0.51531.85870.35260.087*
C190.0423 (5)1.8118 (3)0.28590 (18)0.0631 (8)
H19A0.09681.85360.28790.076*
C120.9535 (6)1.2079 (4)0.46490 (18)0.0778 (9)
H12A0.87191.13760.48200.093*
C161.0265 (5)1.3774 (4)0.36929 (18)0.0721 (9)
H16A0.99331.42270.32150.086*
C200.2004 (6)1.8749 (3)0.32606 (19)0.0748 (9)
H20A0.16881.96210.35590.090*
C141.2476 (6)1.3470 (5)0.4857 (2)0.0931 (11)
H14A1.36411.37100.51690.112*
C151.1998 (6)1.4135 (5)0.4154 (2)0.0915 (11)
H15A1.28351.48270.39860.110*
C131.1247 (6)1.2457 (5)0.5102 (2)0.0958 (12)
H13A1.15751.20170.55830.115*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.0764 (3)0.0699 (2)0.0733 (2)0.01787 (16)0.00824 (16)0.01757 (16)
O10.0458 (12)0.0633 (12)0.0861 (14)0.0045 (9)0.0008 (10)0.0130 (10)
O20.0662 (12)0.0404 (9)0.0529 (11)0.0038 (8)0.0035 (9)0.0007 (8)
N20.0512 (14)0.0594 (14)0.0609 (14)0.0033 (11)0.0100 (11)0.0006 (11)
N10.0467 (12)0.0456 (12)0.0524 (12)0.0060 (9)0.0012 (10)0.0012 (9)
C30.0587 (17)0.0502 (15)0.0470 (14)0.0080 (12)0.0096 (12)0.0009 (11)
O30.1015 (17)0.0571 (12)0.0724 (14)0.0305 (12)0.0110 (12)0.0155 (10)
C170.0480 (15)0.0415 (13)0.0508 (14)0.0003 (11)0.0052 (11)0.0084 (11)
C70.0484 (16)0.0452 (14)0.0505 (15)0.0058 (11)0.0038 (12)0.0022 (11)
C40.0607 (18)0.0470 (15)0.0564 (16)0.0070 (12)0.0089 (13)0.0052 (12)
C60.0468 (15)0.0446 (14)0.0477 (14)0.0042 (11)0.0048 (11)0.0015 (11)
C80.0499 (15)0.0448 (14)0.0533 (15)0.0007 (11)0.0031 (12)0.0011 (11)
C20.0429 (15)0.0668 (18)0.0640 (17)0.0027 (13)0.0073 (13)0.0078 (14)
C100.0697 (18)0.0393 (14)0.0529 (16)0.0020 (13)0.0046 (13)0.0002 (12)
C50.0464 (15)0.0509 (15)0.0597 (16)0.0084 (12)0.0055 (12)0.0009 (12)
C180.0504 (16)0.0462 (14)0.0551 (16)0.0057 (12)0.0070 (12)0.0133 (12)
N30.0502 (14)0.0616 (15)0.0707 (16)0.0059 (11)0.0052 (12)0.0054 (12)
C10.0476 (16)0.0549 (16)0.0633 (17)0.0046 (12)0.0095 (13)0.0093 (13)
C90.0585 (16)0.0489 (15)0.0519 (15)0.0098 (12)0.0093 (12)0.0006 (12)
C220.0541 (17)0.0493 (16)0.080 (2)0.0081 (13)0.0049 (14)0.0004 (14)
C110.0685 (18)0.0447 (14)0.0460 (14)0.0036 (12)0.0016 (12)0.0014 (11)
C210.084 (2)0.0511 (17)0.085 (2)0.0206 (16)0.0047 (18)0.0065 (15)
C190.0685 (19)0.0480 (16)0.0713 (19)0.0103 (14)0.0190 (15)0.0072 (14)
C120.095 (2)0.083 (2)0.0592 (19)0.0282 (19)0.0034 (17)0.0146 (17)
C160.083 (2)0.075 (2)0.0601 (18)0.0211 (17)0.0040 (16)0.0129 (15)
C200.103 (3)0.0417 (16)0.081 (2)0.0013 (16)0.0285 (19)0.0060 (15)
C140.088 (3)0.121 (3)0.072 (2)0.034 (2)0.017 (2)0.006 (2)
C150.093 (3)0.105 (3)0.082 (2)0.043 (2)0.009 (2)0.017 (2)
C130.109 (3)0.120 (3)0.059 (2)0.035 (3)0.021 (2)0.020 (2)
Geometric parameters (Å, º) top
Br1—C31.891 (3)C5—H5A0.9300
O1—C71.210 (3)C18—N31.375 (4)
O2—C101.355 (3)C18—C191.399 (4)
O2—C81.435 (3)C1—H1A0.9300
N2—N31.305 (3)C9—H9A0.9700
N2—N11.355 (3)C9—H9B0.9700
N1—C171.360 (3)C22—C211.367 (4)
N1—C91.448 (3)C22—H22A0.9300
C3—C41.374 (4)C11—C121.379 (4)
C3—C21.385 (4)C11—C161.380 (4)
O3—C101.195 (3)C21—C201.409 (5)
C17—C181.386 (4)C21—H21A0.9300
C17—C221.394 (4)C19—C201.353 (4)
C7—C61.485 (4)C19—H19A0.9300
C7—C81.535 (3)C12—C131.369 (5)
C4—C51.372 (4)C12—H12A0.9300
C4—H4A0.9300C16—C151.382 (4)
C6—C11.387 (4)C16—H16A0.9300
C6—C51.402 (3)C20—H20A0.9300
C8—C91.527 (4)C14—C131.362 (5)
C8—H8A0.9800C14—C151.368 (5)
C2—C11.373 (4)C14—H14A0.9300
C2—H2B0.9300C15—H15A0.9300
C10—C111.480 (4)C13—H13A0.9300
C10—O2—C8115.31 (19)C2—C1—C6120.8 (2)
N3—N2—N1108.8 (2)C2—C1—H1A119.6
N2—N1—C17110.4 (2)C6—C1—H1A119.6
N2—N1—C9119.2 (2)N1—C9—C8112.8 (2)
C17—N1—C9130.4 (2)N1—C9—H9A109.0
C4—C3—C2120.3 (2)C8—C9—H9A109.0
C4—C3—Br1120.3 (2)N1—C9—H9B109.0
C2—C3—Br1119.3 (2)C8—C9—H9B109.0
N1—C17—C18103.9 (2)H9A—C9—H9B107.8
N1—C17—C22133.2 (2)C21—C22—C17115.7 (3)
C18—C17—C22122.9 (2)C21—C22—H22A122.1
O1—C7—C6122.2 (2)C17—C22—H22A122.1
O1—C7—C8119.0 (2)C12—C11—C16119.2 (3)
C6—C7—C8118.8 (2)C12—C11—C10118.4 (3)
C5—C4—C3119.7 (2)C16—C11—C10122.3 (2)
C5—C4—H4A120.1C22—C21—C20122.1 (3)
C3—C4—H4A120.1C22—C21—H21A119.0
C1—C6—C5118.3 (2)C20—C21—H21A119.0
C1—C6—C7123.6 (2)C20—C19—C18117.5 (3)
C5—C6—C7118.1 (2)C20—C19—H19A121.2
O2—C8—C9105.9 (2)C18—C19—H19A121.2
O2—C8—C7109.4 (2)C13—C12—C11119.9 (3)
C9—C8—C7110.1 (2)C13—C12—H12A120.1
O2—C8—H8A110.4C11—C12—H12A120.1
C9—C8—H8A110.4C11—C16—C15120.3 (3)
C7—C8—H8A110.4C11—C16—H16A119.9
C1—C2—C3120.0 (2)C15—C16—H16A119.9
C1—C2—H2B120.0C19—C20—C21121.7 (3)
C3—C2—H2B120.0C19—C20—H20A119.1
O3—C10—O2122.4 (2)C21—C20—H20A119.1
O3—C10—C11125.0 (2)C13—C14—C15120.0 (3)
O2—C10—C11112.5 (2)C13—C14—H14A120.0
C4—C5—C6121.0 (2)C15—C14—H14A120.0
C4—C5—H5A119.5C14—C15—C16119.7 (3)
C6—C5—H5A119.5C14—C15—H15A120.1
N3—C18—C17109.1 (2)C16—C15—H15A120.1
N3—C18—C19130.8 (3)C14—C13—C12120.9 (3)
C17—C18—C19120.1 (3)C14—C13—H13A119.5
N2—N3—C18107.9 (2)C12—C13—H13A119.5
N3—N2—N1—C170.3 (3)N1—N2—N3—C180.2 (3)
N3—N2—N1—C9178.5 (2)C17—C18—N3—N20.5 (3)
N2—N1—C17—C180.6 (3)C19—C18—N3—N2179.8 (3)
C9—N1—C17—C18178.5 (2)C3—C2—C1—C60.8 (4)
N2—N1—C17—C22180.0 (3)C5—C6—C1—C21.6 (4)
C9—N1—C17—C222.0 (5)C7—C6—C1—C2178.1 (3)
C2—C3—C4—C51.5 (4)N2—N1—C9—C894.5 (3)
Br1—C3—C4—C5177.8 (2)C17—N1—C9—C883.3 (3)
O1—C7—C6—C1174.0 (3)O2—C8—C9—N181.7 (3)
C8—C7—C6—C14.7 (4)C7—C8—C9—N1160.1 (2)
O1—C7—C6—C55.7 (4)N1—C17—C22—C21179.5 (3)
C8—C7—C6—C5175.6 (2)C18—C17—C22—C210.1 (4)
C10—O2—C8—C9175.1 (2)O3—C10—C11—C1214.4 (4)
C10—O2—C8—C766.3 (3)O2—C10—C11—C12167.9 (3)
O1—C7—C8—O218.8 (3)O3—C10—C11—C16161.4 (3)
C6—C7—C8—O2162.4 (2)O2—C10—C11—C1616.3 (4)
O1—C7—C8—C997.1 (3)C17—C22—C21—C200.2 (5)
C6—C7—C8—C981.6 (3)N3—C18—C19—C20179.9 (3)
C4—C3—C2—C10.8 (4)C17—C18—C19—C200.3 (4)
Br1—C3—C2—C1178.6 (2)C16—C11—C12—C130.5 (5)
C8—O2—C10—O310.9 (4)C10—C11—C12—C13176.5 (3)
C8—O2—C10—C11166.9 (2)C12—C11—C16—C150.0 (5)
C3—C4—C5—C60.7 (4)C10—C11—C16—C15175.8 (3)
C1—C6—C5—C40.8 (4)C18—C19—C20—C210.4 (5)
C7—C6—C5—C4178.9 (2)C22—C21—C20—C190.4 (5)
N1—C17—C18—N30.7 (3)C13—C14—C15—C160.0 (7)
C22—C17—C18—N3179.8 (2)C11—C16—C15—C140.3 (6)
N1—C17—C18—C19179.6 (2)C15—C14—C13—C120.5 (7)
C22—C17—C18—C190.1 (4)C11—C12—C13—C140.8 (6)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C16—H16A···Cg1i0.932.783.571144
C21—H21A···O3ii0.932.473.202 (4)136
Symmetry codes: (i) x+1, y, z; (ii) x, y+1, z.

Experimental details

Crystal data
Chemical formulaC22H16BrN3O3
Mr450.28
Crystal system, space groupTriclinic, P1
Temperature (K)293
a, b, c (Å)6.4390 (12), 8.8267 (17), 17.430 (3)
α, β, γ (°)88.589 (3), 85.024 (3), 83.087 (3)
V3)979.6 (3)
Z2
Radiation typeMo Kα
µ (mm1)2.13
Crystal size (mm)0.42 × 0.12 × 0.10
Data collection
DiffractometerSiemens SMART 1000 CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.469, 0.815
No. of measured, independent and
observed [I > 2σ(I)] reflections
5526, 3773, 2885
Rint0.015
(sin θ/λ)max1)0.618
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.040, 0.101, 1.04
No. of reflections3773
No. of parameters262
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.45, 0.33

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

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C16—H16A···Cg1i0.932.7783.571143.94
C21—H21A···O3ii0.932.4723.202 (4)135.50
Symmetry codes: (i) x+1, y, z; (ii) x, y+1, z.
 

Acknowledgements

This project was supported by the Natural Science Foundation of Shandong Province (grant Nos. Y2008B02 and Y2008B32).

References

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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
First citationXu, L. Z., Zhang, S. S. & Hu, Z. Q. (2003). Chem. Res. Chin. Univ. 19, 310–313.  CAS Google Scholar
First citationZhang, S.-S., Wan, J., Peng, Z.-Z. & Bi, S. (2006). Acta Cryst. E62, o4348–o4349.  Web of Science CSD CrossRef IUCr Journals Google Scholar

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