organic compounds
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
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 intermolecular C—H⋯O and C—H⋯π interactions help to consolidate the packing.
Related literature
For background, see Chen & Wu (2005). For reference structural data, see: Allen et al. (1987).
Experimental
Crystal data
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Refinement
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Data collection: SMART (Bruker, 1997); cell SAINT (Bruker, 1997); data reduction: SAINT; 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.
Supporting information
10.1107/S1600536808011963/hb2721sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536808011963/hb2721Isup2.hkl
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.
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).
Data collection: SMART (Bruker, 1997); cell
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).Fig. 1. The molecular structure of (I), drawn with 50% probability ellipsoids (arbitrary spheres for the H atoms). |
C23H17Cl2N3O3 | F(000) = 936 |
Mr = 454.30 | Dx = 1.476 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 5663 reflections |
a = 9.3395 (19) Å | θ = 1.7–27.9° |
b = 9.3065 (19) Å | µ = 0.35 mm−1 |
c = 23.538 (5) Å | T = 113 K |
β = 92.10 (3)° | Slab, colourless |
V = 2044.5 (7) Å3 | 0.18 × 0.16 × 0.08 mm |
Z = 4 |
Bruker SMART CCD diffractometer | 3585 independent reflections |
Radiation source: X-ray tube | 3138 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.031 |
ω scans | θmax = 25.0°, θmin = 2.4° |
Absorption correction: multi-scan (SADABS; Bruker, 1997) | h = −11→10 |
Tmin = 0.940, Tmax = 0.973 | k = −11→10 |
11260 measured reflections | l = −27→20 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.033 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.091 | H-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 parameters | Δρmax = 0.24 e Å−3 |
0 restraints | Δρmin = −0.30 e Å−3 |
C23H17Cl2N3O3 | V = 2044.5 (7) Å3 |
Mr = 454.30 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 9.3395 (19) Å | µ = 0.35 mm−1 |
b = 9.3065 (19) Å | T = 113 K |
c = 23.538 (5) Å | 0.18 × 0.16 × 0.08 mm |
β = 92.10 (3)° |
Bruker SMART CCD diffractometer | 3585 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 1997) | 3138 reflections with I > 2σ(I) |
Tmin = 0.940, Tmax = 0.973 | Rint = 0.031 |
11260 measured reflections |
R[F2 > 2σ(F2)] = 0.033 | 0 restraints |
wR(F2) = 0.091 | H-atom parameters constrained |
S = 1.10 | Δρmax = 0.24 e Å−3 |
3585 reflections | Δρmin = −0.30 e Å−3 |
281 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
Cl1 | 0.16956 (4) | 0.45085 (4) | 0.044626 (17) | 0.02736 (13) | |
Cl2 | 0.48958 (4) | 0.53198 (5) | −0.135572 (17) | 0.03077 (14) | |
O1 | 0.28238 (12) | 1.07298 (12) | 0.10792 (5) | 0.0272 (3) | |
O2 | 0.37879 (10) | 0.80863 (11) | 0.11568 (4) | 0.0208 (3) | |
O3 | 0.14534 (11) | 0.76130 (12) | 0.09646 (5) | 0.0309 (3) | |
N1 | 0.58217 (13) | 0.98801 (13) | 0.18828 (6) | 0.0199 (3) | |
N2 | 0.61195 (13) | 1.10055 (14) | 0.22405 (6) | 0.0255 (3) | |
N3 | 0.71818 (13) | 1.17383 (14) | 0.20467 (6) | 0.0279 (3) | |
C1 | 0.22159 (14) | 1.10721 (16) | 0.20360 (7) | 0.0189 (3) | |
C2 | 0.18316 (15) | 1.04219 (16) | 0.25408 (7) | 0.0194 (3) | |
H2 | 0.1983 | 0.9441 | 0.2590 | 0.023* | |
C3 | 0.12259 (14) | 1.12125 (16) | 0.29721 (7) | 0.0209 (3) | |
C4 | 0.10223 (15) | 1.26887 (16) | 0.28894 (7) | 0.0228 (4) | |
H4 | 0.0603 | 1.3232 | 0.3170 | 0.027* | |
C5 | 0.14371 (15) | 1.33491 (17) | 0.23954 (7) | 0.0244 (4) | |
H5 | 0.1320 | 1.4336 | 0.2352 | 0.029* | |
C6 | 0.20216 (15) | 1.25563 (16) | 0.19677 (7) | 0.0231 (4) | |
H6 | 0.2287 | 1.3004 | 0.1634 | 0.028* | |
C7 | 0.08028 (17) | 1.05045 (18) | 0.35132 (7) | 0.0272 (4) | |
H7A | −0.0178 | 1.0198 | 0.3476 | 0.041* | |
H7B | 0.0908 | 1.1176 | 0.3822 | 0.041* | |
H7C | 0.1407 | 0.9687 | 0.3588 | 0.041* | |
C8 | 0.27983 (15) | 1.02509 (16) | 0.15583 (7) | 0.0197 (3) | |
C9 | 0.34219 (15) | 0.87504 (16) | 0.16804 (6) | 0.0198 (3) | |
H9 | 0.2707 | 0.8162 | 0.1867 | 0.024* | |
C10 | 0.26778 (15) | 0.75666 (16) | 0.08292 (7) | 0.0213 (3) | |
C11 | 0.32137 (15) | 0.69822 (16) | 0.02907 (7) | 0.0194 (3) | |
C12 | 0.28115 (15) | 0.56368 (16) | 0.00791 (7) | 0.0193 (3) | |
C13 | 0.33423 (15) | 0.51230 (17) | −0.04221 (6) | 0.0212 (4) | |
H13 | 0.3086 | 0.4214 | −0.0555 | 0.025* | |
C14 | 0.42553 (15) | 0.59738 (17) | −0.07222 (7) | 0.0221 (3) | |
C15 | 0.46799 (15) | 0.73162 (17) | −0.05280 (7) | 0.0239 (4) | |
H15 | 0.5301 | 0.7878 | −0.0734 | 0.029* | |
C16 | 0.41582 (15) | 0.77997 (17) | −0.00211 (7) | 0.0220 (3) | |
H16 | 0.4445 | 0.8696 | 0.0116 | 0.026* | |
C17 | 0.47953 (15) | 0.87985 (16) | 0.20522 (7) | 0.0210 (3) | |
H17A | 0.4545 | 0.8983 | 0.2442 | 0.025* | |
H17B | 0.5251 | 0.7863 | 0.2043 | 0.025* | |
C18 | 0.67506 (14) | 0.98839 (16) | 0.14484 (7) | 0.0188 (3) | |
C19 | 0.69518 (16) | 0.89704 (17) | 0.09888 (7) | 0.0227 (4) | |
H19 | 0.6366 | 0.8177 | 0.0919 | 0.027* | |
C20 | 0.80604 (16) | 0.93045 (19) | 0.06451 (8) | 0.0300 (4) | |
H20 | 0.8227 | 0.8727 | 0.0332 | 0.036* | |
C21 | 0.89552 (17) | 1.05053 (19) | 0.07554 (8) | 0.0342 (4) | |
H21 | 0.9701 | 1.0692 | 0.0515 | 0.041* | |
C22 | 0.87541 (16) | 1.13949 (18) | 0.12039 (8) | 0.0301 (4) | |
H22 | 0.9346 | 1.2184 | 0.1273 | 0.036* | |
C23 | 0.76221 (15) | 1.10800 (16) | 0.15590 (7) | 0.0239 (4) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0300 (2) | 0.0263 (2) | 0.0262 (2) | −0.00985 (15) | 0.00706 (17) | −0.00106 (17) |
Cl2 | 0.0362 (2) | 0.0404 (3) | 0.0161 (2) | 0.00522 (17) | 0.00562 (18) | −0.00085 (17) |
O1 | 0.0329 (6) | 0.0272 (6) | 0.0216 (7) | −0.0044 (5) | 0.0046 (5) | 0.0035 (5) |
O2 | 0.0188 (5) | 0.0247 (6) | 0.0192 (6) | −0.0027 (4) | 0.0041 (4) | −0.0069 (5) |
O3 | 0.0210 (6) | 0.0373 (7) | 0.0351 (8) | −0.0070 (5) | 0.0090 (5) | −0.0115 (6) |
N1 | 0.0210 (6) | 0.0172 (6) | 0.0214 (8) | 0.0009 (5) | 0.0001 (5) | −0.0044 (5) |
N2 | 0.0260 (7) | 0.0209 (7) | 0.0294 (8) | 0.0027 (5) | −0.0027 (6) | −0.0096 (6) |
N3 | 0.0238 (7) | 0.0219 (7) | 0.0378 (9) | −0.0003 (5) | −0.0015 (6) | −0.0053 (7) |
C1 | 0.0153 (7) | 0.0201 (8) | 0.0212 (9) | −0.0003 (6) | −0.0013 (6) | −0.0009 (7) |
C2 | 0.0160 (7) | 0.0183 (8) | 0.0241 (9) | 0.0002 (5) | 0.0013 (6) | −0.0017 (7) |
C3 | 0.0144 (7) | 0.0257 (8) | 0.0224 (9) | 0.0005 (6) | −0.0013 (6) | −0.0035 (7) |
C4 | 0.0166 (7) | 0.0245 (8) | 0.0271 (9) | 0.0026 (6) | −0.0012 (6) | −0.0086 (7) |
C5 | 0.0225 (8) | 0.0176 (8) | 0.0326 (10) | 0.0027 (6) | −0.0056 (7) | −0.0015 (7) |
C6 | 0.0209 (8) | 0.0227 (8) | 0.0253 (9) | −0.0012 (6) | −0.0028 (7) | 0.0036 (7) |
C7 | 0.0264 (8) | 0.0320 (9) | 0.0234 (9) | −0.0006 (7) | 0.0050 (7) | −0.0050 (7) |
C8 | 0.0166 (7) | 0.0215 (8) | 0.0210 (9) | −0.0056 (6) | 0.0023 (6) | 0.0008 (7) |
C9 | 0.0225 (8) | 0.0196 (8) | 0.0176 (8) | −0.0022 (6) | 0.0072 (6) | −0.0030 (6) |
C10 | 0.0211 (8) | 0.0195 (8) | 0.0235 (9) | −0.0036 (6) | 0.0029 (7) | −0.0005 (7) |
C11 | 0.0174 (7) | 0.0218 (8) | 0.0188 (9) | 0.0011 (6) | −0.0008 (6) | −0.0005 (7) |
C12 | 0.0172 (7) | 0.0213 (8) | 0.0194 (8) | −0.0012 (6) | −0.0006 (6) | 0.0026 (6) |
C13 | 0.0239 (8) | 0.0206 (8) | 0.0189 (9) | 0.0014 (6) | −0.0025 (7) | −0.0015 (7) |
C14 | 0.0231 (8) | 0.0293 (9) | 0.0140 (8) | 0.0059 (6) | 0.0010 (6) | 0.0024 (7) |
C15 | 0.0231 (8) | 0.0275 (9) | 0.0211 (9) | −0.0013 (6) | 0.0020 (7) | 0.0063 (7) |
C16 | 0.0228 (8) | 0.0214 (8) | 0.0217 (9) | −0.0023 (6) | 0.0005 (7) | 0.0014 (7) |
C17 | 0.0242 (8) | 0.0204 (8) | 0.0185 (9) | 0.0015 (6) | 0.0038 (6) | −0.0006 (7) |
C18 | 0.0164 (7) | 0.0171 (7) | 0.0230 (9) | 0.0025 (6) | −0.0006 (6) | 0.0016 (6) |
C19 | 0.0208 (7) | 0.0224 (8) | 0.0249 (9) | −0.0005 (6) | 0.0003 (7) | −0.0030 (7) |
C20 | 0.0250 (8) | 0.0346 (10) | 0.0305 (10) | 0.0012 (7) | 0.0047 (7) | −0.0046 (8) |
C21 | 0.0231 (9) | 0.0382 (10) | 0.0418 (12) | −0.0030 (7) | 0.0100 (8) | 0.0046 (9) |
C22 | 0.0224 (8) | 0.0237 (9) | 0.0442 (12) | −0.0049 (6) | −0.0004 (8) | 0.0019 (8) |
C23 | 0.0209 (8) | 0.0173 (8) | 0.0332 (10) | 0.0016 (6) | −0.0039 (7) | −0.0020 (7) |
Cl1—C12 | 1.7326 (15) | C8—C9 | 1.536 (2) |
Cl2—C14 | 1.7370 (16) | C9—C17 | 1.527 (2) |
O1—C8 | 1.2136 (19) | C9—H9 | 0.9800 |
O2—C10 | 1.3582 (18) | C10—C11 | 1.483 (2) |
O2—C9 | 1.4313 (18) | C11—C16 | 1.394 (2) |
O3—C10 | 1.1990 (18) | C11—C12 | 1.394 (2) |
N1—C18 | 1.365 (2) | C12—C13 | 1.382 (2) |
N1—N2 | 1.3660 (18) | C13—C14 | 1.377 (2) |
N1—C17 | 1.4557 (19) | C13—H13 | 0.9300 |
N2—N3 | 1.3004 (19) | C14—C15 | 1.383 (2) |
N3—C23 | 1.377 (2) | C15—C16 | 1.381 (2) |
C1—C2 | 1.392 (2) | C15—H15 | 0.9300 |
C1—C6 | 1.402 (2) | C16—H16 | 0.9300 |
C1—C8 | 1.480 (2) | C17—H17A | 0.9700 |
C2—C3 | 1.391 (2) | C17—H17B | 0.9700 |
C2—H2 | 0.9300 | C18—C19 | 1.394 (2) |
C3—C4 | 1.400 (2) | C18—C23 | 1.398 (2) |
C3—C7 | 1.500 (2) | C19—C20 | 1.373 (2) |
C4—C5 | 1.383 (2) | C19—H19 | 0.9300 |
C4—H4 | 0.9300 | C20—C21 | 1.414 (2) |
C5—C6 | 1.377 (2) | C20—H20 | 0.9300 |
C5—H5 | 0.9300 | C21—C22 | 1.360 (3) |
C6—H6 | 0.9300 | C21—H21 | 0.9300 |
C7—H7A | 0.9600 | C22—C23 | 1.403 (2) |
C7—H7B | 0.9600 | C22—H22 | 0.9300 |
C7—H7C | 0.9600 | ||
C10—O2—C9 | 116.18 (11) | C16—C11—C12 | 118.02 (15) |
C18—N1—N2 | 109.82 (12) | C16—C11—C10 | 119.32 (14) |
C18—N1—C17 | 130.54 (13) | C12—C11—C10 | 122.67 (14) |
N2—N1—C17 | 118.85 (13) | C13—C12—C11 | 121.03 (14) |
N3—N2—N1 | 109.06 (13) | C13—C12—Cl1 | 117.22 (12) |
N2—N3—C23 | 108.31 (13) | C11—C12—Cl1 | 121.69 (12) |
C2—C1—C6 | 119.34 (14) | C14—C13—C12 | 119.16 (15) |
C2—C1—C8 | 122.52 (14) | C14—C13—H13 | 120.4 |
C6—C1—C8 | 118.13 (14) | C12—C13—H13 | 120.4 |
C3—C2—C1 | 121.17 (14) | C13—C14—C15 | 121.67 (15) |
C3—C2—H2 | 119.4 | C13—C14—Cl2 | 118.56 (13) |
C1—C2—H2 | 119.4 | C15—C14—Cl2 | 119.77 (12) |
C2—C3—C4 | 118.33 (15) | C16—C15—C14 | 118.29 (14) |
C2—C3—C7 | 120.96 (14) | C16—C15—H15 | 120.9 |
C4—C3—C7 | 120.72 (14) | C14—C15—H15 | 120.9 |
C5—C4—C3 | 120.83 (15) | C15—C16—C11 | 121.81 (15) |
C5—C4—H4 | 119.6 | C15—C16—H16 | 119.1 |
C3—C4—H4 | 119.6 | C11—C16—H16 | 119.1 |
C6—C5—C4 | 120.49 (15) | N1—C17—C9 | 114.27 (12) |
C6—C5—H5 | 119.8 | N1—C17—H17A | 108.7 |
C4—C5—H5 | 119.8 | C9—C17—H17A | 108.7 |
C5—C6—C1 | 119.82 (15) | N1—C17—H17B | 108.7 |
C5—C6—H6 | 120.1 | C9—C17—H17B | 108.7 |
C1—C6—H6 | 120.1 | H17A—C17—H17B | 107.6 |
C3—C7—H7A | 109.5 | N1—C18—C19 | 133.41 (14) |
C3—C7—H7B | 109.5 | N1—C18—C23 | 104.14 (14) |
H7A—C7—H7B | 109.5 | C19—C18—C23 | 122.41 (15) |
C3—C7—H7C | 109.5 | C20—C19—C18 | 116.44 (15) |
H7A—C7—H7C | 109.5 | C20—C19—H19 | 121.8 |
H7B—C7—H7C | 109.5 | C18—C19—H19 | 121.8 |
O1—C8—C1 | 122.46 (14) | C19—C20—C21 | 121.62 (17) |
O1—C8—C9 | 119.18 (14) | C19—C20—H20 | 119.2 |
C1—C8—C9 | 118.34 (13) | C21—C20—H20 | 119.2 |
O2—C9—C17 | 106.50 (11) | C22—C21—C20 | 121.75 (16) |
O2—C9—C8 | 109.41 (12) | C22—C21—H21 | 119.1 |
C17—C9—C8 | 112.67 (12) | C20—C21—H21 | 119.1 |
O2—C9—H9 | 109.4 | C21—C22—C23 | 117.64 (15) |
C17—C9—H9 | 109.4 | C21—C22—H22 | 121.2 |
C8—C9—H9 | 109.4 | C23—C22—H22 | 121.2 |
O3—C10—O2 | 123.50 (15) | N3—C23—C18 | 108.66 (14) |
O3—C10—C11 | 126.53 (14) | N3—C23—C22 | 131.17 (14) |
O2—C10—C11 | 109.96 (12) | C18—C23—C22 | 120.13 (15) |
C18—N1—N2—N3 | 1.08 (16) | C10—C11—C12—Cl1 | −2.4 (2) |
C17—N1—N2—N3 | 171.98 (12) | C11—C12—C13—C14 | −1.6 (2) |
N1—N2—N3—C23 | −1.23 (16) | Cl1—C12—C13—C14 | −178.78 (11) |
C6—C1—C2—C3 | 1.6 (2) | C12—C13—C14—C15 | 1.5 (2) |
C8—C1—C2—C3 | −177.02 (13) | C12—C13—C14—Cl2 | −179.24 (11) |
C1—C2—C3—C4 | −0.6 (2) | C13—C14—C15—C16 | −0.3 (2) |
C1—C2—C3—C7 | 179.50 (13) | Cl2—C14—C15—C16 | −179.58 (11) |
C2—C3—C4—C5 | −1.2 (2) | C14—C15—C16—C11 | −0.8 (2) |
C7—C3—C4—C5 | 178.73 (13) | C12—C11—C16—C15 | 0.7 (2) |
C3—C4—C5—C6 | 1.9 (2) | C10—C11—C16—C15 | −179.33 (13) |
C4—C5—C6—C1 | −0.9 (2) | C18—N1—C17—C9 | −77.26 (19) |
C2—C1—C6—C5 | −0.9 (2) | N2—N1—C17—C9 | 114.04 (14) |
C8—C1—C6—C5 | 177.82 (13) | O2—C9—C17—N1 | 74.44 (15) |
C2—C1—C8—O1 | 162.53 (14) | C8—C9—C17—N1 | −45.52 (17) |
C6—C1—C8—O1 | −16.1 (2) | N2—N1—C18—C19 | 177.33 (15) |
C2—C1—C8—C9 | −18.9 (2) | C17—N1—C18—C19 | 7.8 (3) |
C6—C1—C8—C9 | 162.47 (13) | N2—N1—C18—C23 | −0.46 (16) |
C10—O2—C9—C17 | 162.00 (12) | C17—N1—C18—C23 | −169.96 (14) |
C10—O2—C9—C8 | −75.96 (15) | N1—C18—C19—C20 | −177.49 (16) |
O1—C8—C9—O2 | −7.23 (18) | C23—C18—C19—C20 | 0.0 (2) |
C1—C8—C9—O2 | 174.12 (11) | C18—C19—C20—C21 | 0.5 (2) |
O1—C8—C9—C17 | 111.04 (15) | C19—C20—C21—C22 | −0.6 (3) |
C1—C8—C9—C17 | −67.61 (17) | C20—C21—C22—C23 | 0.2 (3) |
C9—O2—C10—O3 | −1.8 (2) | N2—N3—C23—C18 | 0.94 (17) |
C9—O2—C10—C11 | 177.09 (12) | N2—N3—C23—C22 | −176.75 (16) |
O3—C10—C11—C16 | 130.70 (17) | N1—C18—C23—N3 | −0.27 (17) |
O2—C10—C11—C16 | −48.10 (18) | C19—C18—C23—N3 | −178.38 (13) |
O3—C10—C11—C12 | −49.3 (2) | N1—C18—C23—C22 | 177.72 (14) |
O2—C10—C11—C12 | 131.91 (14) | C19—C18—C23—C22 | −0.4 (2) |
C16—C11—C12—C13 | 0.5 (2) | C21—C22—C23—N3 | 177.76 (16) |
C10—C11—C12—C13 | −179.47 (13) | C21—C22—C23—C18 | 0.3 (2) |
C16—C11—C12—Cl1 | 177.60 (11) |
D—H···A | D—H | H···A | D···A | 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+1/2, −z+1/2. |
Experimental details
Crystal data | |
Chemical formula | C23H17Cl2N3O3 |
Mr | 454.30 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 113 |
a, b, c (Å) | 9.3395 (19), 9.3065 (19), 23.538 (5) |
β (°) | 92.10 (3) |
V (Å3) | 2044.5 (7) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.35 |
Crystal size (mm) | 0.18 × 0.16 × 0.08 |
Data collection | |
Diffractometer | Bruker SMART CCD diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 1997) |
Tmin, Tmax | 0.940, 0.973 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 11260, 3585, 3138 |
Rint | 0.031 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.033, 0.091, 1.10 |
No. of reflections | 3585 |
No. of parameters | 281 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.24, −0.30 |
Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).
D—H···A | D—H | H···A | D···A | 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+1/2, −z+1/2. |
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. CrossRef Web of Science Google Scholar
Bruker (1997). SMART, SAINT and SADABS. Bruker AXS, Inc., Madison, Wisconsin, USA. Google Scholar
Chen, Z.-Y. & Wu, M.-J. (2005). Org. Lett. 7, 475–477. Web of Science CrossRef PubMed CAS Google Scholar
Sheldrick, 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.
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.