PMCCPMCCPMCC

Search tips
Search criteria 

Advanced

 
Logo of actaeInternational Union of Crystallographysearchopen accessarticle submissionjournal home pagethis article
 
Acta Crystallogr Sect E Struct Rep Online. 2009 February 1; 65(Pt 2): o392.
Published online 2009 January 28. doi:  10.1107/S1600536809002608
PMCID: PMC2968290

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

Abstract

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 [triangle]). For the synthesis, see: Zhang et al. (2006 [triangle]). For bond-length data, see: Allen et al. (1987 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-0o392-scheme1.jpg

Experimental

Crystal data

  • C22H16BrN3O3
  • M r = 450.28
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-0o392-efi1.jpg
  • 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 [triangle]) T min = 0.469, T max = 0.815
  • 5526 measured reflections
  • 3773 independent reflections
  • 2885 reflections with I > 2σ(I)
  • R int = 0.015

Refinement

  • R[F 2 > 2σ(F 2)] = 0.040
  • wR(F 2) = 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

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
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809002608/at2710sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809002608/at2710Isup2.hkl

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

Acknowledgments

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

supplementary crystallographic information

Comment

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).

Experimental

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

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).

Figures

Fig. 1.
The structure of the compound (I) showing 50% probability displacement ellipsoids and the atom numbering scheme.
Fig. 2.
A packing diagram of (I), viewed down the a axis. Hydrogen bonds are indicated by dashed lines.

Crystal data

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

Siemens SMART 1000 CCD area-detector diffractometer3773 independent reflections
Radiation source: fine-focus sealed tube2885 reflections with I > 2σ(I)
graphiteRint = 0.015
Detector resolution: 8.33 pixels mm-1θmax = 26.0°, θmin = 2.3°
ω scansh = −5→7
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)k = −8→10
Tmin = 0.469, Tmax = 0.815l = −21→21
5526 measured reflections

Refinement

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 = 1.04w = 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

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
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)
H4A0.58620.6915−0.04510.067*
C60.5140 (4)1.0130 (3)−0.13989 (14)0.0471 (6)
C80.5243 (4)1.2583 (3)−0.22507 (15)0.0499 (6)
H8A0.39931.2305−0.24700.060*
C20.1912 (4)0.9376 (3)−0.08071 (16)0.0582 (7)
H2B0.04610.9562−0.07100.070*
C100.7238 (4)1.2242 (3)−0.34460 (15)0.0544 (7)
C50.6206 (4)0.8806 (3)−0.10897 (15)0.0535 (6)
H5A0.76560.8612−0.11850.064*
C180.0959 (4)1.6813 (3)−0.24132 (15)0.0511 (6)
N3−0.0275 (4)1.5931 (3)−0.19522 (14)0.0624 (6)
C10.2975 (4)1.0380 (3)−0.12556 (16)0.0560 (7)
H1A0.22351.1238−0.14660.067*
C90.4638 (4)1.3866 (3)−0.16730 (15)0.0541 (6)
H9A0.41941.3430−0.11780.065*
H9B0.58631.4376−0.16080.065*
C220.4686 (5)1.6847 (3)−0.28088 (18)0.0610 (7)
H22A0.60801.6432−0.27930.073*
C110.9024 (4)1.2743 (3)−0.39390 (15)0.0535 (6)
C210.4115 (5)1.8121 (3)−0.3239 (2)0.0726 (9)
H21A0.51531.8587−0.35260.087*
C190.0423 (5)1.8118 (3)−0.28590 (18)0.0631 (8)
H19A−0.09681.8536−0.28790.076*
C120.9535 (6)1.2079 (4)−0.46490 (18)0.0778 (9)
H12A0.87191.1376−0.48200.093*
C161.0265 (5)1.3774 (4)−0.36929 (18)0.0721 (9)
H16A0.99331.4227−0.32150.086*
C200.2004 (6)1.8749 (3)−0.32606 (19)0.0748 (9)
H20A0.16881.9621−0.35590.090*
C141.2476 (6)1.3470 (5)−0.4857 (2)0.0931 (11)
H14A1.36411.3710−0.51690.112*
C151.1998 (6)1.4135 (5)−0.4154 (2)0.0915 (11)
H15A1.28351.4827−0.39860.110*
C131.1247 (6)1.2457 (5)−0.5102 (2)0.0958 (12)
H13A1.15751.2017−0.55830.115*

Atomic displacement parameters (Å2)

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, °)

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—C17−0.3 (3)N1—N2—N3—C18−0.2 (3)
N3—N2—N1—C9−178.5 (2)C17—C18—N3—N20.5 (3)
N2—N1—C17—C180.6 (3)C19—C18—N3—N2−179.8 (3)
C9—N1—C17—C18178.5 (2)C3—C2—C1—C6−0.8 (4)
N2—N1—C17—C22−180.0 (3)C5—C6—C1—C21.6 (4)
C9—N1—C17—C22−2.0 (5)C7—C6—C1—C2−178.1 (3)
C2—C3—C4—C51.5 (4)N2—N1—C9—C894.5 (3)
Br1—C3—C4—C5−177.8 (2)C17—N1—C9—C8−83.3 (3)
O1—C7—C6—C1174.0 (3)O2—C8—C9—N181.7 (3)
C8—C7—C6—C1−4.7 (4)C7—C8—C9—N1−160.1 (2)
O1—C7—C6—C5−5.7 (4)N1—C17—C22—C21−179.5 (3)
C8—C7—C6—C5175.6 (2)C18—C17—C22—C21−0.1 (4)
C10—O2—C8—C9−175.1 (2)O3—C10—C11—C1214.4 (4)
C10—O2—C8—C766.3 (3)O2—C10—C11—C12−167.9 (3)
O1—C7—C8—O218.8 (3)O3—C10—C11—C16−161.4 (3)
C6—C7—C8—O2−162.4 (2)O2—C10—C11—C1616.3 (4)
O1—C7—C8—C9−97.1 (3)C17—C22—C21—C200.2 (5)
C6—C7—C8—C981.6 (3)N3—C18—C19—C20−179.9 (3)
C4—C3—C2—C1−0.8 (4)C17—C18—C19—C20−0.3 (4)
Br1—C3—C2—C1178.6 (2)C16—C11—C12—C13−0.5 (5)
C8—O2—C10—O310.9 (4)C10—C11—C12—C13−176.5 (3)
C8—O2—C10—C11−166.9 (2)C12—C11—C16—C150.0 (5)
C3—C4—C5—C6−0.7 (4)C10—C11—C16—C15175.8 (3)
C1—C6—C5—C4−0.8 (4)C18—C19—C20—C210.4 (5)
C7—C6—C5—C4178.9 (2)C22—C21—C20—C19−0.4 (5)
N1—C17—C18—N3−0.7 (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—C12−0.5 (7)
C22—C17—C18—C190.1 (4)C11—C12—C13—C140.8 (6)

Hydrogen-bond geometry (Å, °)

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.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: AT2710).

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.
  • Nardelli, M. (1995). J. Appl. Cryst.28, 659.
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Siemens (1996). SMART and SAINT Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.
  • Spek, A. L. (2003). J. Appl. Cryst.36, 7–13.
  • Xu, L. Z., Zhang, S. S. & Hu, Z. Q. (2003). Chem. Res. Chin. Univ.19, 310–313.
  • Zhang, S.-S., Wan, J., Peng, Z.-Z. & Bi, S. (2006). Acta Cryst. E62, o4348–o4349.

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