Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807036331/rz2151sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807036331/rz2151Isup2.hkl |
CCDC reference: 660215
Key indicators
- Single-crystal X-ray study
- T = 294 K
- Mean (C-C) = 0.004 Å
- R factor = 0.049
- wR factor = 0.140
- Data-to-parameter ratio = 15.2
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT230_ALERT_2_C Hirshfeld Test Diff for C16 - C17 .. 5.63 su
Alert level G PLAT793_ALERT_1_G Check the Absolute Configuration of C8 = ... S
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
For a general background on the pharmacological activities of benzotriazoles, see: Chen & Wu (2005). For related literature, see: Allen et al. (1987).
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-phenylpropan-1-one (5.0 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 a saturated sodium bicarbonate solution and brine, dried over anhydrous magnesium sulfate and the chloroform solution filtered. This fraction was cooled with ice-water, then a solution of 4-methylbenzoic acid (2.7 g, 0.02 mol) in acetone (10 ml) and triethylamine (2.8 ml) was added. The mixture was stirred with ice-water for about 6 h. The solution was then filtered and concentrated. Single crystals suitable for X-ray analysis were obtained by slow evaporation of an acetone-ethylacetate (1:1 v/v) solution at room temperature over a period of one week.
All H atoms were located in difference Fourier maps and constrained to ride on their parent atoms, with C—H distances in the range 0.93–0.97 Å, and with Uiso(H) = 1.2 Ueq(C) or 1.5 Ueq(C) for the methyl group.
1H-Benzotriazole and its derivatives are an important class of compounds because they exhibit a broad spectrum of pharmacological activities such as antifungal, antitumor and antineoplastic activities (Chen & Wu, 2005). We report here the synthesis and crystal structure of the title compound as part of our ongoing studies on new benzotriazole compounds with higher bioactivity.
In the title compound (Fig. 1), all bond lengths and angles are within normal ranges (Allen et al., 1987). The benzotriazole ring system is essentially planar, with a dihedral angle of 2.67 (1)° between the triazole ring (atoms N1—N3/C1/C6) and the benzene ring (C1—C6). The dihedral angles between the mean planes of the benzotriazole system and the six-membered aromatic rings C10—C15 and C17—C22 are 6.85 (1) and 66.06 (1)°, respectively. The dihedral angle between these two latter rings is 61.7 (2)°. In the crystal structure, intermolecular C—H···O hydrogen bonds (Table1) link the molecules into chains running parallel to the c axis. Adjacent chains are assembled into two-dimensional layers via C—H···N hydrogen bonds (Fig. 2). The packing is further stabilized by π···π interactions occurring between symmetry-related triazole and phenyl rings [Cg1···Cg2i = 3.578 (3) Å; perpendicular interplanar distance = 3.568 (3) Å; Cg1 and Cg2 are the centroids of the N1—N3/C1/C6 triazole ring and C10—C15 phenyl ring, respectively; symmetry code: (i) 1/2 - x, 1/2 - y, 2 - z].
For a general background on the pharmacological activities of benzotriazoles, see: Chen & Wu (2005). For related literature, see: Allen et al. (1987).
Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.
C23H19N3O3 | F(000) = 1616 |
Mr = 385.41 | Dx = 1.314 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -C 2yc | Cell parameters from 1885 reflections |
a = 20.376 (4) Å | θ = 2.3–22.6° |
b = 19.648 (4) Å | µ = 0.09 mm−1 |
c = 10.213 (2) Å | T = 294 K |
β = 107.605 (4)° | Block, colourless |
V = 3897.3 (13) Å3 | 0.22 × 0.18 × 0.12 mm |
Z = 8 |
Siemens SMART CCD area-detector diffractometer | 3994 independent reflections |
Radiation source: fine-focus sealed tube | 2014 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.046 |
φ and ω scans | θmax = 26.4°, θmin = 1.5° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −16→25 |
Tmin = 0.981, Tmax = 0.989 | k = −24→20 |
11106 measured reflections | l = −12→9 |
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)] = 0.049 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.140 | H-atom parameters constrained |
S = 1.00 | w = 1/[σ2(Fo2) + (0.063P)2 + 0.064P] where P = (Fo2 + 2Fc2)/3 |
3994 reflections | (Δ/σ)max = 0.004 |
263 parameters | Δρmax = 0.26 e Å−3 |
0 restraints | Δρmin = −0.17 e Å−3 |
C23H19N3O3 | V = 3897.3 (13) Å3 |
Mr = 385.41 | Z = 8 |
Monoclinic, C2/c | Mo Kα radiation |
a = 20.376 (4) Å | µ = 0.09 mm−1 |
b = 19.648 (4) Å | T = 294 K |
c = 10.213 (2) Å | 0.22 × 0.18 × 0.12 mm |
β = 107.605 (4)° |
Siemens SMART CCD area-detector diffractometer | 3994 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 2014 reflections with I > 2σ(I) |
Tmin = 0.981, Tmax = 0.989 | Rint = 0.046 |
11106 measured reflections |
R[F2 > 2σ(F2)] = 0.049 | 0 restraints |
wR(F2) = 0.140 | H-atom parameters constrained |
S = 1.00 | Δρmax = 0.26 e Å−3 |
3994 reflections | Δρmin = −0.17 e Å−3 |
263 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 | ||
O1 | 0.20658 (8) | 0.12677 (8) | 0.70219 (18) | 0.0703 (5) | |
O2 | 0.14502 (7) | 0.05617 (7) | 0.86281 (16) | 0.0550 (4) | |
O3 | 0.05904 (9) | 0.06461 (9) | 0.6674 (2) | 0.0879 (6) | |
N1 | 0.36982 (10) | 0.14012 (10) | 1.0086 (2) | 0.0598 (5) | |
N2 | 0.30975 (10) | 0.16959 (9) | 0.9822 (2) | 0.0581 (5) | |
N3 | 0.26645 (9) | 0.12819 (9) | 1.02305 (18) | 0.0471 (5) | |
C1 | 0.36587 (11) | 0.07846 (11) | 1.0694 (2) | 0.0475 (6) | |
C2 | 0.41650 (11) | 0.02937 (13) | 1.1214 (3) | 0.0624 (7) | |
H2 | 0.4608 | 0.0342 | 1.1146 | 0.075* | |
C3 | 0.39807 (13) | −0.02585 (13) | 1.1825 (3) | 0.0703 (8) | |
H3 | 0.4306 | −0.0596 | 1.2180 | 0.084* | |
C4 | 0.33142 (12) | −0.03349 (12) | 1.1938 (3) | 0.0648 (7) | |
H4 | 0.3213 | −0.0718 | 1.2377 | 0.078* | |
C5 | 0.28111 (11) | 0.01386 (11) | 1.1421 (2) | 0.0538 (6) | |
H5 | 0.2368 | 0.0086 | 1.1482 | 0.065* | |
C6 | 0.30000 (10) | 0.07063 (10) | 1.0794 (2) | 0.0431 (5) | |
C7 | 0.19630 (11) | 0.14953 (11) | 1.0045 (2) | 0.0542 (6) | |
H7A | 0.1953 | 0.1987 | 1.0130 | 0.065* | |
H7B | 0.1808 | 0.1300 | 1.0773 | 0.065* | |
C8 | 0.14636 (11) | 0.12887 (11) | 0.8666 (2) | 0.0519 (6) | |
H8 | 0.1003 | 0.1457 | 0.8609 | 0.062* | |
C9 | 0.16798 (11) | 0.15841 (12) | 0.7499 (2) | 0.0524 (6) | |
C10 | 0.14402 (11) | 0.22827 (11) | 0.7005 (2) | 0.0500 (6) | |
C11 | 0.18920 (13) | 0.27258 (14) | 0.6695 (3) | 0.0662 (7) | |
H11 | 0.2345 | 0.2593 | 0.6824 | 0.079* | |
C12 | 0.16787 (18) | 0.33635 (15) | 0.6197 (3) | 0.0817 (9) | |
H12 | 0.1990 | 0.3665 | 0.6008 | 0.098* | |
C13 | 0.1012 (2) | 0.35565 (15) | 0.5977 (3) | 0.0873 (10) | |
H13 | 0.0868 | 0.3988 | 0.5632 | 0.105* | |
C14 | 0.05536 (15) | 0.31160 (16) | 0.6266 (3) | 0.0809 (9) | |
H14 | 0.0097 | 0.3245 | 0.6106 | 0.097* | |
C15 | 0.07713 (12) | 0.24794 (13) | 0.6795 (3) | 0.0642 (7) | |
H15 | 0.0463 | 0.2183 | 0.7009 | 0.077* | |
C16 | 0.09767 (11) | 0.02871 (13) | 0.7527 (3) | 0.0605 (7) | |
C17 | 0.09855 (10) | −0.04588 (12) | 0.7526 (2) | 0.0522 (6) | |
C18 | 0.05402 (11) | −0.08051 (14) | 0.6424 (2) | 0.0627 (7) | |
H18 | 0.0250 | −0.0563 | 0.5694 | 0.075* | |
C19 | 0.05285 (12) | −0.15056 (14) | 0.6412 (3) | 0.0636 (7) | |
H19 | 0.0227 | −0.1730 | 0.5670 | 0.076* | |
C20 | 0.09510 (12) | −0.18837 (13) | 0.7469 (3) | 0.0597 (7) | |
C21 | 0.13932 (12) | −0.15321 (13) | 0.8558 (3) | 0.0611 (6) | |
H21 | 0.1684 | −0.1776 | 0.9284 | 0.073* | |
C22 | 0.14135 (12) | −0.08347 (12) | 0.8595 (2) | 0.0597 (7) | |
H22 | 0.1716 | −0.0613 | 0.9340 | 0.072* | |
C23 | 0.09377 (14) | −0.26485 (13) | 0.7461 (3) | 0.0859 (9) | |
H23A | 0.1385 | −0.2819 | 0.7507 | 0.129* | |
H23B | 0.0607 | −0.2806 | 0.6632 | 0.129* | |
H23C | 0.0812 | −0.2809 | 0.8241 | 0.129* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0719 (11) | 0.0785 (12) | 0.0655 (12) | 0.0248 (9) | 0.0282 (10) | 0.0047 (9) |
O2 | 0.0508 (9) | 0.0517 (10) | 0.0530 (11) | −0.0020 (7) | 0.0011 (8) | 0.0017 (8) |
O3 | 0.0787 (13) | 0.0800 (13) | 0.0767 (14) | −0.0005 (10) | −0.0187 (10) | 0.0139 (11) |
N1 | 0.0540 (12) | 0.0652 (14) | 0.0566 (14) | −0.0139 (10) | 0.0112 (10) | 0.0065 (10) |
N2 | 0.0613 (13) | 0.0522 (12) | 0.0573 (14) | −0.0143 (10) | 0.0124 (10) | 0.0042 (10) |
N3 | 0.0496 (11) | 0.0458 (11) | 0.0425 (12) | −0.0046 (9) | 0.0087 (9) | −0.0003 (9) |
C1 | 0.0451 (13) | 0.0523 (14) | 0.0410 (14) | −0.0127 (11) | 0.0065 (10) | −0.0011 (11) |
C2 | 0.0433 (13) | 0.0721 (18) | 0.0647 (18) | −0.0037 (13) | 0.0059 (12) | 0.0003 (14) |
C3 | 0.0598 (17) | 0.0604 (17) | 0.077 (2) | 0.0031 (13) | 0.0007 (14) | 0.0091 (14) |
C4 | 0.0644 (17) | 0.0558 (16) | 0.0639 (18) | −0.0124 (13) | 0.0040 (13) | 0.0122 (13) |
C5 | 0.0488 (13) | 0.0560 (15) | 0.0517 (16) | −0.0076 (12) | 0.0079 (11) | 0.0042 (12) |
C6 | 0.0437 (12) | 0.0437 (13) | 0.0363 (13) | −0.0070 (10) | 0.0037 (10) | −0.0021 (10) |
C7 | 0.0607 (15) | 0.0494 (14) | 0.0532 (16) | 0.0033 (11) | 0.0182 (12) | 0.0002 (11) |
C8 | 0.0467 (13) | 0.0529 (15) | 0.0520 (16) | 0.0078 (11) | 0.0087 (11) | 0.0023 (12) |
C9 | 0.0439 (13) | 0.0620 (16) | 0.0468 (15) | 0.0083 (12) | 0.0072 (11) | −0.0041 (12) |
C10 | 0.0558 (14) | 0.0502 (14) | 0.0396 (14) | 0.0047 (12) | 0.0079 (11) | −0.0036 (11) |
C11 | 0.0646 (16) | 0.0695 (18) | 0.0588 (17) | −0.0023 (14) | 0.0101 (13) | −0.0005 (14) |
C12 | 0.111 (3) | 0.065 (2) | 0.068 (2) | −0.0196 (18) | 0.0262 (18) | −0.0009 (16) |
C13 | 0.136 (3) | 0.0563 (18) | 0.062 (2) | 0.024 (2) | 0.019 (2) | 0.0025 (15) |
C14 | 0.084 (2) | 0.084 (2) | 0.070 (2) | 0.0360 (18) | 0.0181 (16) | 0.0020 (17) |
C15 | 0.0630 (16) | 0.0662 (17) | 0.0630 (18) | 0.0133 (13) | 0.0183 (13) | 0.0049 (14) |
C16 | 0.0463 (14) | 0.0723 (19) | 0.0525 (17) | −0.0045 (13) | −0.0007 (12) | 0.0066 (14) |
C17 | 0.0469 (13) | 0.0599 (16) | 0.0456 (15) | −0.0069 (11) | 0.0074 (11) | 0.0016 (12) |
C18 | 0.0523 (15) | 0.079 (2) | 0.0481 (16) | −0.0104 (13) | 0.0026 (12) | 0.0011 (13) |
C19 | 0.0606 (16) | 0.079 (2) | 0.0513 (17) | −0.0233 (14) | 0.0168 (13) | −0.0140 (14) |
C20 | 0.0667 (16) | 0.0667 (17) | 0.0547 (17) | −0.0143 (13) | 0.0319 (14) | −0.0076 (14) |
C21 | 0.0711 (17) | 0.0628 (17) | 0.0472 (16) | −0.0055 (13) | 0.0145 (13) | −0.0017 (13) |
C22 | 0.0612 (15) | 0.0623 (17) | 0.0468 (16) | −0.0076 (12) | 0.0033 (12) | −0.0037 (13) |
C23 | 0.106 (2) | 0.071 (2) | 0.090 (2) | −0.0212 (16) | 0.0433 (18) | −0.0181 (16) |
O1—C9 | 1.214 (2) | C10—C11 | 1.372 (3) |
O2—C16 | 1.353 (3) | C11—C12 | 1.373 (4) |
O2—C8 | 1.429 (2) | C11—H11 | 0.9300 |
O3—C16 | 1.209 (3) | C12—C13 | 1.362 (4) |
N1—N2 | 1.306 (2) | C12—H12 | 0.9300 |
N1—C1 | 1.375 (3) | C13—C14 | 1.369 (4) |
N2—N3 | 1.356 (2) | C13—H13 | 0.9300 |
N3—C6 | 1.356 (3) | C14—C15 | 1.381 (4) |
N3—C7 | 1.446 (3) | C14—H14 | 0.9300 |
C1—C6 | 1.385 (3) | C15—H15 | 0.9300 |
C1—C2 | 1.395 (3) | C16—C17 | 1.466 (3) |
C2—C3 | 1.360 (3) | C17—C22 | 1.386 (3) |
C2—H2 | 0.9300 | C17—C18 | 1.391 (3) |
C3—C4 | 1.405 (3) | C18—C19 | 1.377 (3) |
C3—H3 | 0.9300 | C18—H18 | 0.9300 |
C4—C5 | 1.367 (3) | C19—C20 | 1.377 (3) |
C4—H4 | 0.9300 | C19—H19 | 0.9300 |
C5—C6 | 1.397 (3) | C20—C21 | 1.386 (3) |
C5—H5 | 0.9300 | C20—C23 | 1.503 (3) |
C7—C8 | 1.522 (3) | C21—C22 | 1.371 (3) |
C7—H7A | 0.9700 | C21—H21 | 0.9300 |
C7—H7B | 0.9700 | C22—H22 | 0.9300 |
C8—C9 | 1.507 (3) | C23—H23A | 0.9600 |
C8—H8 | 0.9800 | C23—H23B | 0.9600 |
C9—C10 | 1.493 (3) | C23—H23C | 0.9600 |
C10—C15 | 1.370 (3) | ||
C16—O2—C8 | 115.11 (18) | C10—C11—C12 | 120.4 (2) |
N2—N1—C1 | 107.75 (18) | C10—C11—H11 | 119.8 |
N1—N2—N3 | 109.08 (18) | C12—C11—H11 | 119.8 |
N2—N3—C6 | 109.84 (17) | C13—C12—C11 | 120.2 (3) |
N2—N3—C7 | 119.70 (18) | C13—C12—H12 | 119.9 |
C6—N3—C7 | 130.46 (18) | C11—C12—H12 | 119.9 |
N1—C1—C6 | 108.76 (19) | C12—C13—C14 | 120.0 (3) |
N1—C1—C2 | 130.1 (2) | C12—C13—H13 | 120.0 |
C6—C1—C2 | 121.1 (2) | C14—C13—H13 | 120.0 |
C3—C2—C1 | 116.8 (2) | C13—C14—C15 | 119.8 (3) |
C3—C2—H2 | 121.6 | C13—C14—H14 | 120.1 |
C1—C2—H2 | 121.6 | C15—C14—H14 | 120.1 |
C2—C3—C4 | 122.1 (2) | C10—C15—C14 | 120.2 (3) |
C2—C3—H3 | 119.0 | C10—C15—H15 | 119.9 |
C4—C3—H3 | 119.0 | C14—C15—H15 | 119.9 |
C5—C4—C3 | 121.7 (2) | O3—C16—O2 | 120.8 (2) |
C5—C4—H4 | 119.1 | O3—C16—C17 | 126.0 (2) |
C3—C4—H4 | 119.1 | O2—C16—C17 | 113.2 (2) |
C4—C5—C6 | 116.3 (2) | C22—C17—C18 | 118.5 (2) |
C4—C5—H5 | 121.9 | C22—C17—C16 | 122.5 (2) |
C6—C5—H5 | 121.9 | C18—C17—C16 | 119.0 (2) |
N3—C6—C1 | 104.56 (18) | C19—C18—C17 | 120.1 (2) |
N3—C6—C5 | 133.4 (2) | C19—C18—H18 | 120.0 |
C1—C6—C5 | 122.0 (2) | C17—C18—H18 | 120.0 |
N3—C7—C8 | 113.69 (18) | C18—C19—C20 | 121.8 (2) |
N3—C7—H7A | 108.8 | C18—C19—H19 | 119.1 |
C8—C7—H7A | 108.8 | C20—C19—H19 | 119.1 |
N3—C7—H7B | 108.8 | C19—C20—C21 | 117.4 (2) |
C8—C7—H7B | 108.8 | C19—C20—C23 | 122.0 (2) |
H7A—C7—H7B | 107.7 | C21—C20—C23 | 120.6 (3) |
O2—C8—C9 | 111.77 (18) | C22—C21—C20 | 121.8 (2) |
O2—C8—C7 | 107.09 (18) | C22—C21—H21 | 119.1 |
C9—C8—C7 | 110.83 (19) | C20—C21—H21 | 119.1 |
O2—C8—H8 | 109.0 | C21—C22—C17 | 120.3 (2) |
C9—C8—H8 | 109.0 | C21—C22—H22 | 119.8 |
C7—C8—H8 | 109.0 | C17—C22—H22 | 119.8 |
O1—C9—C10 | 121.4 (2) | C20—C23—H23A | 109.5 |
O1—C9—C8 | 120.0 (2) | C20—C23—H23B | 109.5 |
C10—C9—C8 | 118.51 (19) | H23A—C23—H23B | 109.5 |
C15—C10—C11 | 119.3 (2) | C20—C23—H23C | 109.5 |
C15—C10—C9 | 121.4 (2) | H23A—C23—H23C | 109.5 |
C11—C10—C9 | 119.2 (2) | H23B—C23—H23C | 109.5 |
C1—N1—N2—N3 | −0.6 (2) | C7—C8—C9—C10 | −87.0 (2) |
N1—N2—N3—C6 | 0.9 (2) | O1—C9—C10—C15 | 138.4 (2) |
N1—N2—N3—C7 | −179.93 (18) | C8—C9—C10—C15 | −44.9 (3) |
N2—N1—C1—C6 | 0.2 (2) | O1—C9—C10—C11 | −38.5 (3) |
N2—N1—C1—C2 | −177.3 (2) | C8—C9—C10—C11 | 138.1 (2) |
N1—C1—C2—C3 | 176.8 (2) | C15—C10—C11—C12 | 0.9 (4) |
C6—C1—C2—C3 | −0.4 (3) | C9—C10—C11—C12 | 177.9 (2) |
C1—C2—C3—C4 | −0.2 (4) | C10—C11—C12—C13 | −1.4 (4) |
C2—C3—C4—C5 | 0.9 (4) | C11—C12—C13—C14 | 0.6 (4) |
C3—C4—C5—C6 | −1.0 (3) | C12—C13—C14—C15 | 0.8 (4) |
N2—N3—C6—C1 | −0.7 (2) | C11—C10—C15—C14 | 0.5 (4) |
C7—N3—C6—C1 | −179.8 (2) | C9—C10—C15—C14 | −176.4 (2) |
N2—N3—C6—C5 | 176.6 (2) | C13—C14—C15—C10 | −1.3 (4) |
C7—N3—C6—C5 | −2.4 (4) | C8—O2—C16—O3 | −1.6 (3) |
N1—C1—C6—N3 | 0.3 (2) | C8—O2—C16—C17 | 179.55 (18) |
C2—C1—C6—N3 | 178.1 (2) | O3—C16—C17—C22 | −175.4 (3) |
N1—C1—C6—C5 | −177.4 (2) | O2—C16—C17—C22 | 3.4 (3) |
C2—C1—C6—C5 | 0.3 (3) | O3—C16—C17—C18 | 3.5 (4) |
C4—C5—C6—N3 | −176.6 (2) | O2—C16—C17—C18 | −177.7 (2) |
C4—C5—C6—C1 | 0.4 (3) | C22—C17—C18—C19 | 0.3 (3) |
N2—N3—C7—C8 | 89.4 (2) | C16—C17—C18—C19 | −178.6 (2) |
C6—N3—C7—C8 | −91.6 (3) | C17—C18—C19—C20 | −0.2 (4) |
C16—O2—C8—C9 | −65.0 (2) | C18—C19—C20—C21 | 0.1 (3) |
C16—O2—C8—C7 | 173.46 (19) | C18—C19—C20—C23 | 179.8 (2) |
N3—C7—C8—O2 | 63.2 (2) | C19—C20—C21—C22 | 0.1 (4) |
N3—C7—C8—C9 | −58.9 (2) | C23—C20—C21—C22 | −179.7 (2) |
O2—C8—C9—O1 | −29.6 (3) | C20—C21—C22—C17 | 0.0 (4) |
C7—C8—C9—O1 | 89.8 (3) | C18—C17—C22—C21 | −0.2 (4) |
O2—C8—C9—C10 | 153.67 (18) | C16—C17—C22—C21 | 178.7 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
C4—H4···O1i | 0.93 | 2.50 | 3.157 (3) | 128 |
C7—H7A···N2ii | 0.97 | 2.59 | 3.560 (3) | 176 |
C18—H18···O3iii | 0.93 | 2.51 | 3.317 (3) | 145 |
Symmetry codes: (i) x, −y, z+1/2; (ii) −x+1/2, −y+1/2, −z+2; (iii) −x, −y, −z+1. |
Experimental details
Crystal data | |
Chemical formula | C23H19N3O3 |
Mr | 385.41 |
Crystal system, space group | Monoclinic, C2/c |
Temperature (K) | 294 |
a, b, c (Å) | 20.376 (4), 19.648 (4), 10.213 (2) |
β (°) | 107.605 (4) |
V (Å3) | 3897.3 (13) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.22 × 0.18 × 0.12 |
Data collection | |
Diffractometer | Siemens SMART CCD area-detector |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.981, 0.989 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 11106, 3994, 2014 |
Rint | 0.046 |
(sin θ/λ)max (Å−1) | 0.626 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.049, 0.140, 1.00 |
No. of reflections | 3994 |
No. of parameters | 263 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.26, −0.17 |
Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1997), SHELXTL.
D—H···A | D—H | H···A | D···A | D—H···A |
C4—H4···O1i | 0.93 | 2.50 | 3.157 (3) | 127.8 |
C7—H7A···N2ii | 0.97 | 2.59 | 3.560 (3) | 176.1 |
C18—H18···O3iii | 0.93 | 2.51 | 3.317 (3) | 145.3 |
Symmetry codes: (i) x, −y, z+1/2; (ii) −x+1/2, −y+1/2, −z+2; (iii) −x, −y, −z+1. |
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1H-Benzotriazole and its derivatives are an important class of compounds because they exhibit a broad spectrum of pharmacological activities such as antifungal, antitumor and antineoplastic activities (Chen & Wu, 2005). We report here the synthesis and crystal structure of the title compound as part of our ongoing studies on new benzotriazole compounds with higher bioactivity.
In the title compound (Fig. 1), all bond lengths and angles are within normal ranges (Allen et al., 1987). The benzotriazole ring system is essentially planar, with a dihedral angle of 2.67 (1)° between the triazole ring (atoms N1—N3/C1/C6) and the benzene ring (C1—C6). The dihedral angles between the mean planes of the benzotriazole system and the six-membered aromatic rings C10—C15 and C17—C22 are 6.85 (1) and 66.06 (1)°, respectively. The dihedral angle between these two latter rings is 61.7 (2)°. In the crystal structure, intermolecular C—H···O hydrogen bonds (Table1) link the molecules into chains running parallel to the c axis. Adjacent chains are assembled into two-dimensional layers via C—H···N hydrogen bonds (Fig. 2). The packing is further stabilized by π···π interactions occurring between symmetry-related triazole and phenyl rings [Cg1···Cg2i = 3.578 (3) Å; perpendicular interplanar distance = 3.568 (3) Å; Cg1 and Cg2 are the centroids of the N1—N3/C1/C6 triazole ring and C10—C15 phenyl ring, respectively; symmetry code: (i) 1/2 - x, 1/2 - y, 2 - z].