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-(4-bromo­benzo­yl)ethyl 2-chloro­benzoate

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

(Received 14 January 2009; accepted 22 January 2009; online 31 January 2009)

In the title compound, C22H15BrClN3O3, the benzotriazole ring system makes dihedral angles of 2.43 (1) and 71.51 (1)° with the bromo­phenyl and chloro­phenyl rings, respectively; the angle between the latter two rings is 69.26 (1)°. In the crystal structure, mol­ecules are linked into chains by inter­molecular C—H⋯O hydrogen bonds. The crystal packing is further stabilized by ππ (with a centroid-centroid distance of 3.764 Å) and C—H⋯π inter­actions.

Related literature

For the crystal structure of a related compound, see: Zeng et al. (2007[Zeng, W.-L., Bi, S. & Wan, J. (2007). Acta Cryst. E63, o1076-o1077.]). For standard 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
  • C22H15BrClN3O3

  • Mr = 484.72

  • Monoclinic, P 21 /c

  • a = 6.2613 (7) Å

  • b = 36.688 (4) Å

  • c = 8.7919 (9) Å

  • β = 90.878 (2)°

  • V = 2019.4 (4) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 2.20 mm−1

  • T = 293 (2) K

  • 0.36 × 0.21 × 0.09 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 = 0.505, Tmax = 0.827

  • 11039 measured reflections

  • 3978 independent reflections

  • 2968 reflections with I > 2σ(I)

  • Rint = 0.025

Refinement
  • R[F2 > 2σ(F2)] = 0.041

  • wR(F2) = 0.103

  • S = 1.04

  • 3978 reflections

  • 271 parameters

  • H-atom parameters constrained

  • Δρmax = 0.48 e Å−3

  • Δρmin = −0.44 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

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

D—H⋯A D—H H⋯A DA D—H⋯A
C16—H16ACg1i 0.93 2.87 3.707 150
C21—H21A⋯O3ii 0.93 2.47 3.101 (4) 126
Symmetry codes: (i) x-1, y, z; (ii) x, y, z+1.

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

The crystal structure of 2-(benzotriazol-1-yl)-1-(4-methylbenzoyl)ethyl 4-ethylbenzoate has been reported by Zeng et al. (2007). In a search for new benzotriazole derivatives with higher bioactivity, the title compound was synthesized and its structure is reported here.

In the title molecule (Fig. 1), all bond lengths (Allen et al., 1987) and angles are within normal ranges. The benzotriazole system is almost planar, with a dihedral angle of 0.89 (1)° between the triazole ring (N1–N3/C17/C18) and the benzene ring A (C17–C22). The benzotriazole mean plane makes dihedral angles of 2.43 (1)° and 71.51 (1)° with benzene rings B (C1–C6) and C (C11–C16), respectively, indicating the non-planarity of the whole molecule. The dihedral angle between rings B and C is 69.26 (1)°.

In the crystal structure (Fig. 2), molecules are linked into chains along the c axis by intermolecular C21—H21A···O3 hydrogen bonds (Table 1). The distance of 3.764 Å between the centroids of rings A and B related by the symmetry code (x, y, -1 + z) suggests a possible π···π interaction. The crystal packing is further stabilized by C—H···π interactions (Table 1).

Related literature top

For the crystal structure of a related compound, see: Zeng et al. (2007). For standard bond-length data, see: Allen et al., (1987).

Experimental top

The title compound was prepared according to the literature method of Zeng 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 six days.

Refinement top

All H atoms were located in difference Fourier maps and constrained to ride on their parent atoms, with C(aromatic)—H = 0.93 Å, C(methylene)—H = 0.97 Å and C(methine)—H = 0.98 Å; 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 molecular structure of the title compound, showing 50% probability displacement ellipsoids and the atom numbering scheme. Hydrogen atoms are represented by spheres of arbitrary radius.
[Figure 2] Fig. 2. A packing diagram, viewed down the a axis. Hydrogen bonds are indicated by dashed lines.
2-(1H-Benzotriazol-1-yl)-1-(4-bromobenzoyl)ethyl 2-chlorobenzoate top
Crystal data top
C22H15BrClN3O3F(000) = 976
Mr = 484.72Dx = 1.594 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 6.2613 (7) ÅCell parameters from 3180 reflections
b = 36.688 (4) Åθ = 2.2–22.9°
c = 8.7919 (9) ŵ = 2.20 mm1
β = 90.878 (2)°T = 293 K
V = 2019.4 (4) Å3Plate, colourless
Z = 40.36 × 0.21 × 0.09 mm
Data collection top
Siemens SMART 1000 CCD area-detector
diffractometer
3978 independent reflections
Radiation source: fine-focus sealed tube2968 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.025
Detector resolution: 8.33 pixels mm-1θmax = 26.1°, θmin = 2.2°
ω scansh = 77
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
k = 4445
Tmin = 0.505, Tmax = 0.827l = 108
11039 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)] = 0.041Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.103H-atom parameters constrained
S = 1.04 w = 1/[σ2(Fo2) + (0.0492P)2 + 0.6802P]
where P = (Fo2 + 2Fc2)/3
3978 reflections(Δ/σ)max < 0.001
271 parametersΔρmax = 0.48 e Å3
0 restraintsΔρmin = 0.44 e Å3
Crystal data top
C22H15BrClN3O3V = 2019.4 (4) Å3
Mr = 484.72Z = 4
Monoclinic, P21/cMo Kα radiation
a = 6.2613 (7) ŵ = 2.20 mm1
b = 36.688 (4) ÅT = 293 K
c = 8.7919 (9) Å0.36 × 0.21 × 0.09 mm
β = 90.878 (2)°
Data collection top
Siemens SMART 1000 CCD area-detector
diffractometer
3978 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
2968 reflections with I > 2σ(I)
Tmin = 0.505, Tmax = 0.827Rint = 0.025
11039 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0410 restraints
wR(F2) = 0.103H-atom parameters constrained
S = 1.04Δρmax = 0.48 e Å3
3978 reflectionsΔρmin = 0.44 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
Br10.29655 (6)0.490655 (9)0.67871 (4)0.06861 (15)
Cl10.06423 (18)0.75440 (3)1.24666 (14)0.0966 (4)
O20.0115 (3)0.64041 (5)1.3681 (2)0.0511 (5)
N10.3152 (3)0.59119 (6)1.5238 (2)0.0427 (5)
C30.1975 (5)0.52390 (8)0.8274 (3)0.0463 (7)
C180.5177 (4)0.61307 (7)1.7051 (3)0.0413 (6)
N20.5149 (4)0.57773 (6)1.5071 (3)0.0518 (6)
O10.2188 (3)0.60500 (7)1.1628 (2)0.0696 (7)
C170.3102 (4)0.61371 (7)1.6470 (3)0.0380 (6)
C50.0818 (5)0.55733 (8)0.9389 (3)0.0501 (7)
H5A0.22470.56420.93990.060*
C60.0564 (4)0.57085 (7)1.0497 (3)0.0406 (6)
C210.2051 (5)0.65309 (8)1.8413 (3)0.0524 (7)
H21A0.10200.66691.88980.063*
C100.0114 (5)0.67132 (8)1.2854 (3)0.0567 (8)
C90.1469 (5)0.58149 (7)1.4157 (3)0.0458 (7)
H9A0.01440.57821.46980.055*
H9B0.18230.55851.36810.055*
O30.0745 (5)0.67563 (7)1.1669 (3)0.0951 (9)
N30.6384 (4)0.59032 (7)1.6152 (3)0.0523 (6)
C200.4137 (5)0.65259 (8)1.9019 (3)0.0524 (7)
H20A0.44460.66591.98950.063*
C190.5718 (5)0.63304 (8)1.8356 (3)0.0510 (7)
H19A0.71020.63301.87550.061*
C220.1482 (5)0.63403 (8)1.7136 (3)0.0486 (7)
H22A0.00990.63461.67360.058*
C20.3391 (5)0.53722 (8)0.9333 (4)0.0550 (8)
H2B0.48180.53030.93060.066*
C80.1142 (5)0.61048 (7)1.2923 (3)0.0472 (7)
H8A0.25160.61811.25100.057*
C10.2703 (4)0.56101 (8)1.0444 (3)0.0491 (7)
H1A0.36710.57041.11540.059*
C40.0131 (5)0.53398 (8)0.8277 (3)0.0527 (8)
H4A0.10790.52520.75400.063*
C70.0336 (5)0.59603 (8)1.1656 (3)0.0472 (7)
C160.3280 (6)0.68352 (9)1.4437 (4)0.0716 (10)
H16A0.34160.65851.45640.086*
C110.1591 (5)0.69699 (8)1.3596 (3)0.0524 (7)
C130.2875 (6)0.75732 (9)1.4121 (5)0.0779 (11)
H13A0.27280.78241.40220.093*
C140.4524 (6)0.74321 (10)1.4933 (5)0.0866 (12)
H14A0.54980.75881.53850.104*
C150.4754 (7)0.70624 (11)1.5085 (5)0.0896 (13)
H15A0.58940.69671.56210.108*
C120.1430 (5)0.73429 (8)1.3451 (4)0.0599 (8)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.0825 (3)0.0610 (2)0.0628 (2)0.00151 (17)0.01525 (18)0.02185 (16)
Cl10.0949 (7)0.0628 (6)0.1336 (10)0.0065 (5)0.0472 (7)0.0038 (6)
O20.0750 (14)0.0417 (11)0.0368 (10)0.0131 (9)0.0022 (9)0.0028 (8)
N10.0460 (13)0.0434 (12)0.0384 (12)0.0057 (10)0.0040 (10)0.0041 (10)
C30.0568 (19)0.0380 (14)0.0443 (16)0.0017 (13)0.0071 (13)0.0027 (12)
C180.0418 (15)0.0445 (15)0.0375 (14)0.0020 (12)0.0005 (12)0.0035 (11)
N20.0537 (15)0.0513 (14)0.0504 (14)0.0146 (12)0.0004 (12)0.0073 (11)
O10.0595 (15)0.0880 (17)0.0607 (14)0.0290 (12)0.0135 (11)0.0193 (12)
C170.0459 (16)0.0347 (13)0.0336 (14)0.0002 (11)0.0031 (12)0.0001 (10)
C50.0438 (16)0.0487 (17)0.0574 (18)0.0037 (13)0.0082 (14)0.0054 (14)
C60.0464 (16)0.0359 (14)0.0394 (14)0.0038 (12)0.0018 (12)0.0002 (11)
C210.062 (2)0.0535 (18)0.0426 (16)0.0045 (14)0.0141 (14)0.0042 (13)
C100.086 (2)0.0446 (16)0.0396 (16)0.0095 (16)0.0076 (16)0.0013 (13)
C90.0574 (18)0.0387 (14)0.0412 (15)0.0020 (13)0.0079 (13)0.0049 (11)
O30.161 (3)0.0665 (16)0.0589 (15)0.0383 (16)0.0511 (16)0.0135 (12)
N30.0454 (14)0.0581 (15)0.0532 (15)0.0105 (12)0.0046 (11)0.0044 (12)
C200.072 (2)0.0463 (16)0.0393 (16)0.0122 (15)0.0065 (15)0.0061 (12)
C190.0537 (18)0.0570 (18)0.0422 (16)0.0130 (14)0.0054 (13)0.0040 (13)
C220.0472 (17)0.0555 (17)0.0433 (16)0.0024 (13)0.0056 (13)0.0001 (13)
C20.0432 (17)0.0538 (18)0.068 (2)0.0020 (14)0.0022 (15)0.0118 (15)
C80.0598 (18)0.0418 (15)0.0401 (15)0.0076 (13)0.0021 (13)0.0074 (12)
C10.0457 (17)0.0488 (16)0.0525 (17)0.0018 (13)0.0093 (13)0.0105 (13)
C40.062 (2)0.0463 (16)0.0499 (17)0.0020 (14)0.0124 (15)0.0095 (13)
C70.0543 (18)0.0456 (16)0.0416 (15)0.0088 (14)0.0065 (13)0.0008 (12)
C160.094 (3)0.0490 (18)0.072 (2)0.0104 (18)0.027 (2)0.0108 (16)
C110.071 (2)0.0450 (16)0.0411 (15)0.0102 (15)0.0085 (14)0.0023 (12)
C130.091 (3)0.0453 (19)0.098 (3)0.0152 (18)0.025 (2)0.0025 (18)
C140.095 (3)0.064 (2)0.102 (3)0.026 (2)0.039 (2)0.004 (2)
C150.093 (3)0.073 (3)0.104 (3)0.014 (2)0.047 (2)0.019 (2)
C120.069 (2)0.0479 (17)0.063 (2)0.0050 (15)0.0135 (16)0.0039 (14)
Geometric parameters (Å, º) top
Br1—C31.899 (3)C10—C111.479 (4)
Cl1—C121.736 (3)C9—C81.531 (4)
O2—C101.353 (3)C9—H9A0.9700
O2—C81.441 (3)C9—H9B0.9700
N1—N21.355 (3)C20—C191.361 (4)
N1—C171.363 (3)C20—H20A0.9300
N1—C91.452 (3)C19—H19A0.9300
C3—C21.366 (4)C22—H22A0.9300
C3—C41.369 (4)C2—C11.384 (4)
C18—N31.382 (3)C2—H2B0.9300
C18—C171.388 (4)C8—C71.532 (4)
C18—C191.399 (4)C8—H8A0.9800
N2—N31.301 (3)C1—H1A0.9300
O1—C71.205 (3)C4—H4A0.9300
C17—C221.395 (4)C16—C151.374 (5)
C5—C41.374 (4)C16—C111.390 (4)
C5—C61.385 (4)C16—H16A0.9300
C5—H5A0.9300C11—C121.378 (4)
C6—C11.388 (4)C13—C141.366 (5)
C6—C71.492 (4)C13—C121.377 (5)
C21—C221.365 (4)C13—H13A0.9300
C21—C201.403 (4)C14—C151.371 (5)
C21—H21A0.9300C14—H14A0.9300
C10—O31.191 (3)C15—H15A0.9300
C10—O2—C8115.7 (2)C21—C22—C17115.9 (3)
N2—N1—C17109.9 (2)C21—C22—H22A122.1
N2—N1—C9120.1 (2)C17—C22—H22A122.1
C17—N1—C9130.0 (2)C3—C2—C1120.1 (3)
C2—C3—C4121.1 (3)C3—C2—H2B120.0
C2—C3—Br1118.9 (2)C1—C2—H2B120.0
C4—C3—Br1120.0 (2)O2—C8—C9104.9 (2)
N3—C18—C17108.5 (2)O2—C8—C7109.3 (2)
N3—C18—C19131.1 (3)C9—C8—C7110.4 (2)
C17—C18—C19120.4 (3)O2—C8—H8A110.7
N3—N2—N1109.3 (2)C9—C8—H8A110.7
N1—C17—C18104.4 (2)C7—C8—H8A110.7
N1—C17—C22133.1 (2)C2—C1—C6119.9 (3)
C18—C17—C22122.5 (2)C2—C1—H1A120.0
C4—C5—C6121.7 (3)C6—C1—H1A120.0
C4—C5—H5A119.2C3—C4—C5118.8 (3)
C6—C5—H5A119.2C3—C4—H4A120.6
C5—C6—C1118.4 (2)C5—C4—H4A120.6
C5—C6—C7117.6 (2)O1—C7—C6121.9 (3)
C1—C6—C7124.0 (2)O1—C7—C8119.4 (3)
C22—C21—C20122.4 (3)C6—C7—C8118.7 (2)
C22—C21—H21A118.8C15—C16—C11121.8 (3)
C20—C21—H21A118.8C15—C16—H16A119.1
O3—C10—O2122.4 (3)C11—C16—H16A119.1
O3—C10—C11126.5 (3)C12—C11—C16117.3 (3)
O2—C10—C11111.0 (2)C12—C11—C10123.0 (3)
N1—C9—C8112.4 (2)C16—C11—C10119.6 (3)
N1—C9—H9A109.1C14—C13—C12119.9 (3)
C8—C9—H9A109.1C14—C13—H13A120.1
N1—C9—H9B109.1C12—C13—H13A120.1
C8—C9—H9B109.1C13—C14—C15120.5 (3)
H9A—C9—H9B107.9C13—C14—H14A119.8
N2—N3—C18108.0 (2)C15—C14—H14A119.8
C19—C20—C21121.5 (3)C14—C15—C16119.2 (4)
C19—C20—H20A119.2C14—C15—H15A120.4
C21—C20—H20A119.2C16—C15—H15A120.4
C20—C19—C18117.3 (3)C13—C12—C11121.4 (3)
C20—C19—H19A121.3C13—C12—Cl1117.0 (3)
C18—C19—H19A121.3C11—C12—Cl1121.6 (2)
C17—N1—N2—N30.7 (3)N1—C9—C8—C7169.5 (2)
C9—N1—N2—N3179.3 (2)C3—C2—C1—C61.1 (5)
N2—N1—C17—C180.3 (3)C5—C6—C1—C22.2 (4)
C9—N1—C17—C18178.8 (2)C7—C6—C1—C2179.5 (3)
N2—N1—C17—C22179.7 (3)C2—C3—C4—C51.3 (5)
C9—N1—C17—C221.8 (5)Br1—C3—C4—C5178.3 (2)
N3—C18—C17—N10.1 (3)C6—C5—C4—C30.1 (4)
C19—C18—C17—N1179.0 (2)C5—C6—C7—O11.2 (4)
N3—C18—C17—C22179.4 (3)C1—C6—C7—O1177.1 (3)
C19—C18—C17—C220.4 (4)C5—C6—C7—C8178.2 (3)
C4—C5—C6—C11.6 (4)C1—C6—C7—C83.5 (4)
C4—C5—C6—C7180.0 (3)O2—C8—C7—O114.2 (4)
C8—O2—C10—O310.7 (5)C9—C8—C7—O1100.7 (3)
C8—O2—C10—C11167.3 (2)O2—C8—C7—C6166.4 (2)
N2—N1—C9—C897.1 (3)C9—C8—C7—C678.7 (3)
C17—N1—C9—C881.3 (3)C15—C16—C11—C120.8 (5)
N1—N2—N3—C180.7 (3)C15—C16—C11—C10176.8 (4)
C17—C18—N3—N20.5 (3)O3—C10—C11—C1232.0 (6)
C19—C18—N3—N2179.3 (3)O2—C10—C11—C12150.1 (3)
C22—C21—C20—C190.3 (5)O3—C10—C11—C16145.5 (4)
C21—C20—C19—C180.7 (4)O2—C10—C11—C1632.4 (4)
N3—C18—C19—C20178.4 (3)C12—C13—C14—C150.0 (7)
C17—C18—C19—C200.3 (4)C13—C14—C15—C161.3 (7)
C20—C21—C22—C170.4 (4)C11—C16—C15—C141.7 (6)
N1—C17—C22—C21178.5 (3)C14—C13—C12—C110.9 (6)
C18—C17—C22—C210.7 (4)C14—C13—C12—Cl1179.0 (3)
C4—C3—C2—C10.7 (5)C16—C11—C12—C130.5 (5)
Br1—C3—C2—C1178.9 (2)C10—C11—C12—C13178.0 (3)
C10—O2—C8—C9172.5 (2)C16—C11—C12—Cl1178.5 (3)
C10—O2—C8—C769.2 (3)C10—C11—C12—Cl13.9 (5)
N1—C9—C8—O272.9 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C16—H16A···Cg1i0.932.873.707150
C21—H21A···O3ii0.932.473.101 (4)126
Symmetry codes: (i) x1, y, z; (ii) x, y, z+1.

Experimental details

Crystal data
Chemical formulaC22H15BrClN3O3
Mr484.72
Crystal system, space groupMonoclinic, P21/c
Temperature (K)293
a, b, c (Å)6.2613 (7), 36.688 (4), 8.7919 (9)
β (°) 90.878 (2)
V3)2019.4 (4)
Z4
Radiation typeMo Kα
µ (mm1)2.20
Crystal size (mm)0.36 × 0.21 × 0.09
Data collection
DiffractometerSiemens SMART 1000 CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.505, 0.827
No. of measured, independent and
observed [I > 2σ(I)] reflections
11039, 3978, 2968
Rint0.025
(sin θ/λ)max1)0.618
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.041, 0.103, 1.04
No. of reflections3978
No. of parameters271
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.48, 0.44

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···Cg1i0.932.8723.707150.22
C21—H21A···O3ii0.932.4663.101 (4)125.71
Symmetry codes: (i) x1, y, z; (ii) x, y, z+1.
 

Acknowledgements

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

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 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 citationZeng, W.-L., Bi, S. & Wan, J. (2007). Acta Cryst. E63, o1076–o1077.  Web of Science CSD CrossRef 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