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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

2-(1H-1,2,3-Benzotriazol-1-yl)-1-m-toluoylethyl 2,4-di­chloro­benzoate

aMicroScale Science Institute, Department of Chemistry and Chemical Engineering, Weifang University, Weifang 261061, People's Republic of China
*Correspondence e-mail: wulanzeng@163.com

(Received 13 April 2008; accepted 25 April 2008; online 30 April 2008)

In the title compound, C23H17Cl2N3O3, the dihedral angles between the mean planes of the benzotriazole system and the methyl- and dichloro-substituted benzene rings are 47.72 (1) and 13.06 (1)°, respectively. In the crystal structure, inter­molecular C—H⋯O and C—H⋯π inter­actions help to consolidate the packing.

Related literature

For background, see Chen & Wu (2005[Chen, Z.-Y. & Wu, M.-J. (2005). Org. Lett. 7, 475-477.]). For reference structural 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
  • C23H17Cl2N3O3

  • Mr = 454.30

  • Monoclinic, P 21 /c

  • a = 9.3395 (19) Å

  • b = 9.3065 (19) Å

  • c = 23.538 (5) Å

  • β = 92.10 (3)°

  • V = 2044.5 (7) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.35 mm−1

  • T = 113 (2) K

  • 0.18 × 0.16 × 0.08 mm

Data collection
  • Bruker SMART CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 1997[Bruker (1997). SMART, SAINT and SADABS. Bruker AXS, Inc., Madison, Wisconsin, USA.]) Tmin = 0.940, Tmax = 0.973

  • 11260 measured reflections

  • 3585 independent reflections

  • 3138 reflections with I > 2σ(I)

  • Rint = 0.031

Refinement
  • R[F2 > 2σ(F2)] = 0.033

  • wR(F2) = 0.091

  • S = 1.10

  • 3585 reflections

  • 281 parameters

  • H-atom parameters constrained

  • Δρmax = 0.24 e Å−3

  • Δρmin = −0.30 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C15—H15⋯O1i 0.93 2.35 3.263 (2) 168
C4—H4⋯Cg1ii 0.93 2.86 3.4645 (19) 124
Symmetry codes: (i) -x+1, -y+2, -z; (ii) [-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]. Cg1 is the centroid of the C18–C23 ring.

Data collection: SMART (Bruker, 1997[Bruker (1997). SMART, SAINT and SADABS. Bruker AXS, Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 1997[Bruker (1997). SMART, SAINT and SADABS. Bruker AXS, 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.

Supporting information


Comment top

1H-Benzotriazole and its derivatives exhibit a broad spectrum of pharmacological activities such as antifungal, antitumor and antineoplastic activities (Chen & Wu, 2005). We report here the synthesis and structure of the title compound, (I) (Fig. 1), as part of our ongoing studies on new benzotriazole compounds with higher bioactivity.

The molecule of (I) is chiral. In the arbitrarily chosen asymmetric molecule, C9 has S configuration, but crystal symmetry generates a racemic mixture. Otherwise, all the bond lengths and angles in (I) are within their normal ranges (Allen et al., 1987). The benzotriazole ring system is essentially planar, with a dihedral angle of 2.2 (8)° between the triazole ring (atoms N1—N3/C18/C23) and the C18—C23 benzene ring. The dihedral angles between the mean planes of the benzotriazole system and the C1—C6 and C11—C15 aromatic rings are 47.72 (1)° and 13.06 (1)°, respectively. The dihedral angle between rings C1—C6 and C11—C15 is 35.26 (2)°.

In the crystal, intermolecular C-H···O and C-H···π interactions (Table 1) help to consolidate the packing.

Related literature top

For background, see Chen & Wu (2005). For reference structural data, see: Allen et al. (1987).

Experimental top

Bromine (3.2 g, 0.02 mol) was added dropwise to a solution of 3-(1H-benzo[d][1,2,3]triazol-1-yl)-1-m-tolylpropan-1-one (5.30 g, 0.02 mol) and sodium acetate (1.6 g, 0.02 mol) in acetic acid (50 ml). The reaction proceeded for 7 h. Water (50 ml) and chloroform (20 ml) were then added. The organic layer was washed successively with saturated sodium bicarbonate solution and brine, dried over anhydrous magnesium sulfate and the chloroform solution filtered. It was cooled with ice-water, and then an acetone solution (10 ml) of 2-chlorobenzoic acid (3.8 g, 0.02 mol) and triethylamine (2.8 ml) was added. The mixture was stirred with ice-water for 6 h. The solution was then filtered and concentrated. Colourless slabs of (I) were obtained by slow evaporation of ethanol solution at room temperature after one week.

Refinement top

The H atoms were geometrically placed (C—H = 0.93–0.97 Å), and refined as riding with Uiso(H) = 1.2Ueq(C) or 1.5Ueq(methyl C).

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); 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).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I), drawn with 50% probability ellipsoids (arbitrary spheres for the H atoms).
2-(1H-1,2,3-Benzotriazol-1-yl)-1-m-toluoylethyl 2,4-dichlorobenzoate top
Crystal data top
C23H17Cl2N3O3F(000) = 936
Mr = 454.30Dx = 1.476 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 5663 reflections
a = 9.3395 (19) Åθ = 1.7–27.9°
b = 9.3065 (19) ŵ = 0.35 mm1
c = 23.538 (5) ÅT = 113 K
β = 92.10 (3)°Slab, colourless
V = 2044.5 (7) Å30.18 × 0.16 × 0.08 mm
Z = 4
Data collection top
Bruker SMART CCD
diffractometer
3585 independent reflections
Radiation source: X-ray tube3138 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.031
ω scansθmax = 25.0°, θmin = 2.4°
Absorption correction: multi-scan
(SADABS; Bruker, 1997)
h = 1110
Tmin = 0.940, Tmax = 0.973k = 1110
11260 measured reflectionsl = 2720
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)] = 0.033Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.091H-atom parameters constrained
S = 1.10 w = 1/[σ2(Fo2) + (0.0569P)2 + 0.0675P]
where P = (Fo2 + 2Fc2)/3
3585 reflections(Δ/σ)max = 0.001
281 parametersΔρmax = 0.24 e Å3
0 restraintsΔρmin = 0.30 e Å3
Crystal data top
C23H17Cl2N3O3V = 2044.5 (7) Å3
Mr = 454.30Z = 4
Monoclinic, P21/cMo Kα radiation
a = 9.3395 (19) ŵ = 0.35 mm1
b = 9.3065 (19) ÅT = 113 K
c = 23.538 (5) Å0.18 × 0.16 × 0.08 mm
β = 92.10 (3)°
Data collection top
Bruker SMART CCD
diffractometer
3585 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 1997)
3138 reflections with I > 2σ(I)
Tmin = 0.940, Tmax = 0.973Rint = 0.031
11260 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0330 restraints
wR(F2) = 0.091H-atom parameters constrained
S = 1.10Δρmax = 0.24 e Å3
3585 reflectionsΔρmin = 0.30 e Å3
281 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
Cl10.16956 (4)0.45085 (4)0.044626 (17)0.02736 (13)
Cl20.48958 (4)0.53198 (5)0.135572 (17)0.03077 (14)
O10.28238 (12)1.07298 (12)0.10792 (5)0.0272 (3)
O20.37879 (10)0.80863 (11)0.11568 (4)0.0208 (3)
O30.14534 (11)0.76130 (12)0.09646 (5)0.0309 (3)
N10.58217 (13)0.98801 (13)0.18828 (6)0.0199 (3)
N20.61195 (13)1.10055 (14)0.22405 (6)0.0255 (3)
N30.71818 (13)1.17383 (14)0.20467 (6)0.0279 (3)
C10.22159 (14)1.10721 (16)0.20360 (7)0.0189 (3)
C20.18316 (15)1.04219 (16)0.25408 (7)0.0194 (3)
H20.19830.94410.25900.023*
C30.12259 (14)1.12125 (16)0.29721 (7)0.0209 (3)
C40.10223 (15)1.26887 (16)0.28894 (7)0.0228 (4)
H40.06031.32320.31700.027*
C50.14371 (15)1.33491 (17)0.23954 (7)0.0244 (4)
H50.13201.43360.23520.029*
C60.20216 (15)1.25563 (16)0.19677 (7)0.0231 (4)
H60.22871.30040.16340.028*
C70.08028 (17)1.05045 (18)0.35132 (7)0.0272 (4)
H7A0.01781.01980.34760.041*
H7B0.09081.11760.38220.041*
H7C0.14070.96870.35880.041*
C80.27983 (15)1.02509 (16)0.15583 (7)0.0197 (3)
C90.34219 (15)0.87504 (16)0.16804 (6)0.0198 (3)
H90.27070.81620.18670.024*
C100.26778 (15)0.75666 (16)0.08292 (7)0.0213 (3)
C110.32137 (15)0.69822 (16)0.02907 (7)0.0194 (3)
C120.28115 (15)0.56368 (16)0.00791 (7)0.0193 (3)
C130.33423 (15)0.51230 (17)0.04221 (6)0.0212 (4)
H130.30860.42140.05550.025*
C140.42553 (15)0.59738 (17)0.07222 (7)0.0221 (3)
C150.46799 (15)0.73162 (17)0.05280 (7)0.0239 (4)
H150.53010.78780.07340.029*
C160.41582 (15)0.77997 (17)0.00211 (7)0.0220 (3)
H160.44450.86960.01160.026*
C170.47953 (15)0.87985 (16)0.20522 (7)0.0210 (3)
H17A0.45450.89830.24420.025*
H17B0.52510.78630.20430.025*
C180.67506 (14)0.98839 (16)0.14484 (7)0.0188 (3)
C190.69518 (16)0.89704 (17)0.09888 (7)0.0227 (4)
H190.63660.81770.09190.027*
C200.80604 (16)0.93045 (19)0.06451 (8)0.0300 (4)
H200.82270.87270.03320.036*
C210.89552 (17)1.05053 (19)0.07554 (8)0.0342 (4)
H210.97011.06920.05150.041*
C220.87541 (16)1.13949 (18)0.12039 (8)0.0301 (4)
H220.93461.21840.12730.036*
C230.76221 (15)1.10800 (16)0.15590 (7)0.0239 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0300 (2)0.0263 (2)0.0262 (2)0.00985 (15)0.00706 (17)0.00106 (17)
Cl20.0362 (2)0.0404 (3)0.0161 (2)0.00522 (17)0.00562 (18)0.00085 (17)
O10.0329 (6)0.0272 (6)0.0216 (7)0.0044 (5)0.0046 (5)0.0035 (5)
O20.0188 (5)0.0247 (6)0.0192 (6)0.0027 (4)0.0041 (4)0.0069 (5)
O30.0210 (6)0.0373 (7)0.0351 (8)0.0070 (5)0.0090 (5)0.0115 (6)
N10.0210 (6)0.0172 (6)0.0214 (8)0.0009 (5)0.0001 (5)0.0044 (5)
N20.0260 (7)0.0209 (7)0.0294 (8)0.0027 (5)0.0027 (6)0.0096 (6)
N30.0238 (7)0.0219 (7)0.0378 (9)0.0003 (5)0.0015 (6)0.0053 (7)
C10.0153 (7)0.0201 (8)0.0212 (9)0.0003 (6)0.0013 (6)0.0009 (7)
C20.0160 (7)0.0183 (8)0.0241 (9)0.0002 (5)0.0013 (6)0.0017 (7)
C30.0144 (7)0.0257 (8)0.0224 (9)0.0005 (6)0.0013 (6)0.0035 (7)
C40.0166 (7)0.0245 (8)0.0271 (9)0.0026 (6)0.0012 (6)0.0086 (7)
C50.0225 (8)0.0176 (8)0.0326 (10)0.0027 (6)0.0056 (7)0.0015 (7)
C60.0209 (8)0.0227 (8)0.0253 (9)0.0012 (6)0.0028 (7)0.0036 (7)
C70.0264 (8)0.0320 (9)0.0234 (9)0.0006 (7)0.0050 (7)0.0050 (7)
C80.0166 (7)0.0215 (8)0.0210 (9)0.0056 (6)0.0023 (6)0.0008 (7)
C90.0225 (8)0.0196 (8)0.0176 (8)0.0022 (6)0.0072 (6)0.0030 (6)
C100.0211 (8)0.0195 (8)0.0235 (9)0.0036 (6)0.0029 (7)0.0005 (7)
C110.0174 (7)0.0218 (8)0.0188 (9)0.0011 (6)0.0008 (6)0.0005 (7)
C120.0172 (7)0.0213 (8)0.0194 (8)0.0012 (6)0.0006 (6)0.0026 (6)
C130.0239 (8)0.0206 (8)0.0189 (9)0.0014 (6)0.0025 (7)0.0015 (7)
C140.0231 (8)0.0293 (9)0.0140 (8)0.0059 (6)0.0010 (6)0.0024 (7)
C150.0231 (8)0.0275 (9)0.0211 (9)0.0013 (6)0.0020 (7)0.0063 (7)
C160.0228 (8)0.0214 (8)0.0217 (9)0.0023 (6)0.0005 (7)0.0014 (7)
C170.0242 (8)0.0204 (8)0.0185 (9)0.0015 (6)0.0038 (6)0.0006 (7)
C180.0164 (7)0.0171 (7)0.0230 (9)0.0025 (6)0.0006 (6)0.0016 (6)
C190.0208 (7)0.0224 (8)0.0249 (9)0.0005 (6)0.0003 (7)0.0030 (7)
C200.0250 (8)0.0346 (10)0.0305 (10)0.0012 (7)0.0047 (7)0.0046 (8)
C210.0231 (9)0.0382 (10)0.0418 (12)0.0030 (7)0.0100 (8)0.0046 (9)
C220.0224 (8)0.0237 (9)0.0442 (12)0.0049 (6)0.0004 (8)0.0019 (8)
C230.0209 (8)0.0173 (8)0.0332 (10)0.0016 (6)0.0039 (7)0.0020 (7)
Geometric parameters (Å, º) top
Cl1—C121.7326 (15)C8—C91.536 (2)
Cl2—C141.7370 (16)C9—C171.527 (2)
O1—C81.2136 (19)C9—H90.9800
O2—C101.3582 (18)C10—C111.483 (2)
O2—C91.4313 (18)C11—C161.394 (2)
O3—C101.1990 (18)C11—C121.394 (2)
N1—C181.365 (2)C12—C131.382 (2)
N1—N21.3660 (18)C13—C141.377 (2)
N1—C171.4557 (19)C13—H130.9300
N2—N31.3004 (19)C14—C151.383 (2)
N3—C231.377 (2)C15—C161.381 (2)
C1—C21.392 (2)C15—H150.9300
C1—C61.402 (2)C16—H160.9300
C1—C81.480 (2)C17—H17A0.9700
C2—C31.391 (2)C17—H17B0.9700
C2—H20.9300C18—C191.394 (2)
C3—C41.400 (2)C18—C231.398 (2)
C3—C71.500 (2)C19—C201.373 (2)
C4—C51.383 (2)C19—H190.9300
C4—H40.9300C20—C211.414 (2)
C5—C61.377 (2)C20—H200.9300
C5—H50.9300C21—C221.360 (3)
C6—H60.9300C21—H210.9300
C7—H7A0.9600C22—C231.403 (2)
C7—H7B0.9600C22—H220.9300
C7—H7C0.9600
C10—O2—C9116.18 (11)C16—C11—C12118.02 (15)
C18—N1—N2109.82 (12)C16—C11—C10119.32 (14)
C18—N1—C17130.54 (13)C12—C11—C10122.67 (14)
N2—N1—C17118.85 (13)C13—C12—C11121.03 (14)
N3—N2—N1109.06 (13)C13—C12—Cl1117.22 (12)
N2—N3—C23108.31 (13)C11—C12—Cl1121.69 (12)
C2—C1—C6119.34 (14)C14—C13—C12119.16 (15)
C2—C1—C8122.52 (14)C14—C13—H13120.4
C6—C1—C8118.13 (14)C12—C13—H13120.4
C3—C2—C1121.17 (14)C13—C14—C15121.67 (15)
C3—C2—H2119.4C13—C14—Cl2118.56 (13)
C1—C2—H2119.4C15—C14—Cl2119.77 (12)
C2—C3—C4118.33 (15)C16—C15—C14118.29 (14)
C2—C3—C7120.96 (14)C16—C15—H15120.9
C4—C3—C7120.72 (14)C14—C15—H15120.9
C5—C4—C3120.83 (15)C15—C16—C11121.81 (15)
C5—C4—H4119.6C15—C16—H16119.1
C3—C4—H4119.6C11—C16—H16119.1
C6—C5—C4120.49 (15)N1—C17—C9114.27 (12)
C6—C5—H5119.8N1—C17—H17A108.7
C4—C5—H5119.8C9—C17—H17A108.7
C5—C6—C1119.82 (15)N1—C17—H17B108.7
C5—C6—H6120.1C9—C17—H17B108.7
C1—C6—H6120.1H17A—C17—H17B107.6
C3—C7—H7A109.5N1—C18—C19133.41 (14)
C3—C7—H7B109.5N1—C18—C23104.14 (14)
H7A—C7—H7B109.5C19—C18—C23122.41 (15)
C3—C7—H7C109.5C20—C19—C18116.44 (15)
H7A—C7—H7C109.5C20—C19—H19121.8
H7B—C7—H7C109.5C18—C19—H19121.8
O1—C8—C1122.46 (14)C19—C20—C21121.62 (17)
O1—C8—C9119.18 (14)C19—C20—H20119.2
C1—C8—C9118.34 (13)C21—C20—H20119.2
O2—C9—C17106.50 (11)C22—C21—C20121.75 (16)
O2—C9—C8109.41 (12)C22—C21—H21119.1
C17—C9—C8112.67 (12)C20—C21—H21119.1
O2—C9—H9109.4C21—C22—C23117.64 (15)
C17—C9—H9109.4C21—C22—H22121.2
C8—C9—H9109.4C23—C22—H22121.2
O3—C10—O2123.50 (15)N3—C23—C18108.66 (14)
O3—C10—C11126.53 (14)N3—C23—C22131.17 (14)
O2—C10—C11109.96 (12)C18—C23—C22120.13 (15)
C18—N1—N2—N31.08 (16)C10—C11—C12—Cl12.4 (2)
C17—N1—N2—N3171.98 (12)C11—C12—C13—C141.6 (2)
N1—N2—N3—C231.23 (16)Cl1—C12—C13—C14178.78 (11)
C6—C1—C2—C31.6 (2)C12—C13—C14—C151.5 (2)
C8—C1—C2—C3177.02 (13)C12—C13—C14—Cl2179.24 (11)
C1—C2—C3—C40.6 (2)C13—C14—C15—C160.3 (2)
C1—C2—C3—C7179.50 (13)Cl2—C14—C15—C16179.58 (11)
C2—C3—C4—C51.2 (2)C14—C15—C16—C110.8 (2)
C7—C3—C4—C5178.73 (13)C12—C11—C16—C150.7 (2)
C3—C4—C5—C61.9 (2)C10—C11—C16—C15179.33 (13)
C4—C5—C6—C10.9 (2)C18—N1—C17—C977.26 (19)
C2—C1—C6—C50.9 (2)N2—N1—C17—C9114.04 (14)
C8—C1—C6—C5177.82 (13)O2—C9—C17—N174.44 (15)
C2—C1—C8—O1162.53 (14)C8—C9—C17—N145.52 (17)
C6—C1—C8—O116.1 (2)N2—N1—C18—C19177.33 (15)
C2—C1—C8—C918.9 (2)C17—N1—C18—C197.8 (3)
C6—C1—C8—C9162.47 (13)N2—N1—C18—C230.46 (16)
C10—O2—C9—C17162.00 (12)C17—N1—C18—C23169.96 (14)
C10—O2—C9—C875.96 (15)N1—C18—C19—C20177.49 (16)
O1—C8—C9—O27.23 (18)C23—C18—C19—C200.0 (2)
C1—C8—C9—O2174.12 (11)C18—C19—C20—C210.5 (2)
O1—C8—C9—C17111.04 (15)C19—C20—C21—C220.6 (3)
C1—C8—C9—C1767.61 (17)C20—C21—C22—C230.2 (3)
C9—O2—C10—O31.8 (2)N2—N3—C23—C180.94 (17)
C9—O2—C10—C11177.09 (12)N2—N3—C23—C22176.75 (16)
O3—C10—C11—C16130.70 (17)N1—C18—C23—N30.27 (17)
O2—C10—C11—C1648.10 (18)C19—C18—C23—N3178.38 (13)
O3—C10—C11—C1249.3 (2)N1—C18—C23—C22177.72 (14)
O2—C10—C11—C12131.91 (14)C19—C18—C23—C220.4 (2)
C16—C11—C12—C130.5 (2)C21—C22—C23—N3177.76 (16)
C10—C11—C12—C13179.47 (13)C21—C22—C23—C180.3 (2)
C16—C11—C12—Cl1177.60 (11)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C15—H15···O1i0.932.353.263 (2)168
C4—H4···Cg1ii0.932.863.4645 (19)124
Symmetry codes: (i) x+1, y+2, z; (ii) x+1, y+1/2, z+1/2.

Experimental details

Crystal data
Chemical formulaC23H17Cl2N3O3
Mr454.30
Crystal system, space groupMonoclinic, P21/c
Temperature (K)113
a, b, c (Å)9.3395 (19), 9.3065 (19), 23.538 (5)
β (°) 92.10 (3)
V3)2044.5 (7)
Z4
Radiation typeMo Kα
µ (mm1)0.35
Crystal size (mm)0.18 × 0.16 × 0.08
Data collection
DiffractometerBruker SMART CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 1997)
Tmin, Tmax0.940, 0.973
No. of measured, independent and
observed [I > 2σ(I)] reflections
11260, 3585, 3138
Rint0.031
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.033, 0.091, 1.10
No. of reflections3585
No. of parameters281
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.24, 0.30

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C15—H15···O1i0.932.353.263 (2)168
C4—H4···Cg1ii0.932.863.4645 (19)124
Symmetry codes: (i) x+1, y+2, z; (ii) x+1, y+1/2, z+1/2.
 

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 citationBruker (1997). SMART, SAINT and SADABS. Bruker AXS, Inc., Madison, Wisconsin, USA.  Google Scholar
First citationChen, Z.-Y. & Wu, M.-J. (2005). Org. Lett. 7, 475–477.  Web of Science CrossRef PubMed CAS Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  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