Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807028632/lh2425sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807028632/lh2425Isup2.hkl |
CCDC reference: 654961
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.002 Å
- R factor = 0.041
- wR factor = 0.116
- Data-to-parameter ratio = 15.4
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ?
Alert level G PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 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
1H-Benzotriazole derivatives can exhibit a broad spectrum of pharmacological activities (Chen & Wu, 2005). For standard bond-length values, see Allen et al. (1987).
To a solution of 1-(4-ethylphenyl)-3-(dimethylamino)propan-1-one (12.05 g, 0.05 mol) in water (25 ml) was added benzotriazole (7.1 g, 0.06 mol). The mixture was heated under reflux for 5 h, yielding a copious precipitate. Colourless single crystals suitable for X-ray diffraction study were obtained by slow evaporation of a ethanol solution over a period of 6 d.
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) and 1.5 Ueq(methyl C) H atoms.
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 structure of the title compound (Fig. 1) as part of our ongoing studies of new benzotriazole compounds with potential bioactivity.
All bond lengths and angles are within normal ranges (Allen et al., 1987). The benzotriazole fused rings system is essentially planar, with a dihedral angle of 0.52 (8)° between the triazole ring (atoms N1—N3/C1/C6) and the benzene ring (C1—C6). The mean plane of the benzotriazole moiety and the benzene ring (C10—C15) make a dihedral angle of 70.50 (6)°. The crystal structure (Fig. 2) is stabilized by weak C—H···O interactions and Van der Waals interactions.
1H-Benzotriazole derivatives can exhibit a broad spectrum of pharmacological activities (Chen & Wu, 2005). For standard bond-length values, see Allen et al. (1987).
Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); 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.
Fig. 1. The molecular structure of (I), drawn with 30% probability ellipsoids. | |
Fig. 2. The crystal packing of (I), viewed along a axis. Hydrogen bonds are indicated by dashed lines. |
C17H17N3O | F(000) = 592 |
Mr = 279.34 | Dx = 1.250 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 2918 reflections |
a = 5.7577 (5) Å | θ = 1.8–26° |
b = 13.9599 (12) Å | µ = 0.08 mm−1 |
c = 18.6746 (17) Å | T = 293 K |
β = 98.585 (5)° | Block, colourless |
V = 1484.2 (2) Å3 | 0.22 × 0.2 × 0.1 mm |
Z = 4 |
Bruker SMART CCD area-detector diffractometer | 2918 independent reflections |
Radiation source: fine-focus sealed tube | 2410 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.020 |
φ and ω scans | θmax = 26.0°, θmin = 1.8° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −7→7 |
Tmin = 0.983, Tmax = 0.99 | k = −16→17 |
15817 measured reflections | l = −18→23 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.041 | H-atom parameters constrained |
wR(F2) = 0.116 | w = 1/[σ2(Fo2) + (0.0572P)2 + 0.2889P] where P = (Fo2 + 2Fc2)/3 |
S = 1.05 | (Δ/σ)max = 0.002 |
2918 reflections | Δρmax = 0.20 e Å−3 |
190 parameters | Δρmin = −0.15 e Å−3 |
0 restraints | Extinction correction: SHELXL97 (Sheldrick, 1997) |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0012 (2) |
C17H17N3O | V = 1484.2 (2) Å3 |
Mr = 279.34 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 5.7577 (5) Å | µ = 0.08 mm−1 |
b = 13.9599 (12) Å | T = 293 K |
c = 18.6746 (17) Å | 0.22 × 0.2 × 0.1 mm |
β = 98.585 (5)° |
Bruker SMART CCD area-detector diffractometer | 2918 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 2410 reflections with I > 2σ(I) |
Tmin = 0.983, Tmax = 0.99 | Rint = 0.020 |
15817 measured reflections |
R[F2 > 2σ(F2)] = 0.041 | 0 restraints |
wR(F2) = 0.116 | H-atom parameters constrained |
S = 1.05 | Δρmax = 0.20 e Å−3 |
2918 reflections | Δρmin = −0.15 e Å−3 |
190 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 | 0.9021 (3) | 0.83688 (8) | 0.58482 (7) | 0.0796 (4) | |
N1 | 0.5033 (2) | 0.66905 (8) | 0.70534 (6) | 0.0481 (3) | |
C2 | 0.5548 (2) | 0.62666 (9) | 0.77141 (7) | 0.0420 (3) | |
N3 | 0.1946 (2) | 0.58572 (10) | 0.71641 (7) | 0.0572 (3) | |
C14 | 1.2945 (3) | 0.73333 (11) | 0.43061 (8) | 0.0552 (4) | |
H14 | 1.4161 | 0.7692 | 0.4166 | 0.066* | |
N2 | 0.2864 (2) | 0.64325 (10) | 0.67354 (7) | 0.0588 (3) | |
C10 | 0.9962 (2) | 0.71539 (9) | 0.50723 (7) | 0.0425 (3) | |
C8 | 0.7275 (2) | 0.68779 (10) | 0.60405 (7) | 0.0449 (3) | |
H8A | 0.8181 | 0.6313 | 0.6206 | 0.054* | |
H8B | 0.5937 | 0.6672 | 0.5697 | 0.054* | |
C9 | 0.8774 (2) | 0.75388 (10) | 0.56663 (8) | 0.0472 (3) | |
C15 | 1.1769 (2) | 0.76740 (10) | 0.48448 (8) | 0.0496 (3) | |
H15 | 1.2195 | 0.8262 | 0.5059 | 0.059* | |
C13 | 1.2344 (3) | 0.64631 (12) | 0.39706 (8) | 0.0551 (4) | |
C4 | 0.3425 (3) | 0.51793 (10) | 0.83957 (8) | 0.0532 (4) | |
H4 | 0.2099 | 0.4819 | 0.8444 | 0.064* | |
C1 | 0.7493 (3) | 0.62898 (11) | 0.82580 (8) | 0.0555 (4) | |
H1 | 0.8818 | 0.6655 | 0.8217 | 0.067* | |
C3 | 0.3548 (2) | 0.57312 (10) | 0.77798 (7) | 0.0440 (3) | |
C11 | 0.9337 (3) | 0.62869 (11) | 0.47349 (8) | 0.0544 (4) | |
H11 | 0.8128 | 0.5926 | 0.4878 | 0.065* | |
C6 | 0.7332 (3) | 0.57433 (13) | 0.88542 (9) | 0.0641 (4) | |
H6 | 0.8591 | 0.5735 | 0.9229 | 0.077* | |
C5 | 0.5333 (3) | 0.51930 (12) | 0.89225 (8) | 0.0607 (4) | |
H5 | 0.5314 | 0.4829 | 0.9338 | 0.073* | |
C16 | 1.3579 (3) | 0.60998 (14) | 0.33634 (9) | 0.0731 (5) | |
H16A | 1.5070 | 0.6428 | 0.3380 | 0.088* | |
H16B | 1.3899 | 0.5421 | 0.3432 | 0.088* | |
C7 | 0.6410 (3) | 0.73464 (11) | 0.66774 (8) | 0.0577 (4) | |
H7A | 0.7745 | 0.7573 | 0.7013 | 0.069* | |
H7B | 0.5452 | 0.7897 | 0.6510 | 0.069* | |
C12 | 1.0502 (3) | 0.59550 (12) | 0.41861 (9) | 0.0618 (4) | |
H12 | 1.0037 | 0.5379 | 0.3958 | 0.074* | |
C17 | 1.2147 (4) | 0.62537 (15) | 0.26425 (10) | 0.0771 (5) | |
H17A | 1.2989 | 0.6020 | 0.2272 | 0.116* | |
H17B | 1.1842 | 0.6926 | 0.2571 | 0.116* | |
H17C | 1.0687 | 0.5915 | 0.2619 | 0.116* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.1232 (11) | 0.0449 (6) | 0.0840 (9) | −0.0106 (6) | 0.0590 (8) | −0.0120 (6) |
N1 | 0.0512 (7) | 0.0521 (7) | 0.0431 (6) | −0.0045 (5) | 0.0134 (5) | 0.0003 (5) |
C2 | 0.0437 (7) | 0.0438 (7) | 0.0407 (7) | 0.0027 (5) | 0.0137 (5) | −0.0045 (6) |
N3 | 0.0505 (7) | 0.0662 (8) | 0.0539 (7) | −0.0089 (6) | 0.0046 (6) | 0.0044 (6) |
C14 | 0.0526 (8) | 0.0623 (9) | 0.0535 (8) | −0.0032 (7) | 0.0174 (7) | 0.0051 (7) |
N2 | 0.0567 (7) | 0.0695 (8) | 0.0488 (7) | −0.0058 (6) | 0.0031 (6) | 0.0045 (6) |
C10 | 0.0486 (7) | 0.0412 (7) | 0.0386 (7) | 0.0026 (5) | 0.0097 (5) | 0.0030 (5) |
C8 | 0.0454 (7) | 0.0465 (7) | 0.0440 (7) | 0.0009 (6) | 0.0108 (6) | 0.0003 (6) |
C9 | 0.0570 (8) | 0.0412 (8) | 0.0452 (7) | 0.0028 (6) | 0.0137 (6) | 0.0019 (6) |
C15 | 0.0552 (8) | 0.0459 (8) | 0.0486 (8) | −0.0045 (6) | 0.0107 (6) | 0.0000 (6) |
C13 | 0.0589 (9) | 0.0618 (9) | 0.0465 (8) | 0.0112 (7) | 0.0143 (7) | 0.0034 (7) |
C4 | 0.0613 (9) | 0.0470 (8) | 0.0552 (9) | −0.0001 (6) | 0.0216 (7) | 0.0024 (6) |
C1 | 0.0442 (8) | 0.0654 (9) | 0.0571 (9) | −0.0005 (7) | 0.0082 (7) | −0.0079 (7) |
C3 | 0.0442 (7) | 0.0443 (7) | 0.0452 (7) | −0.0004 (5) | 0.0120 (6) | −0.0028 (6) |
C11 | 0.0622 (9) | 0.0499 (8) | 0.0549 (8) | −0.0089 (7) | 0.0209 (7) | −0.0053 (7) |
C6 | 0.0625 (10) | 0.0759 (11) | 0.0506 (9) | 0.0130 (8) | −0.0017 (7) | −0.0022 (8) |
C5 | 0.0803 (11) | 0.0581 (9) | 0.0458 (8) | 0.0148 (8) | 0.0163 (7) | 0.0082 (7) |
C16 | 0.0795 (12) | 0.0811 (12) | 0.0638 (11) | 0.0194 (9) | 0.0275 (9) | −0.0006 (9) |
C7 | 0.0739 (10) | 0.0502 (8) | 0.0550 (9) | −0.0078 (7) | 0.0298 (8) | −0.0002 (7) |
C12 | 0.0793 (11) | 0.0517 (9) | 0.0576 (9) | −0.0035 (8) | 0.0206 (8) | −0.0125 (7) |
C17 | 0.0878 (13) | 0.0887 (13) | 0.0602 (10) | −0.0042 (10) | 0.0281 (9) | −0.0035 (9) |
O1—C9 | 1.2098 (17) | C13—C16 | 1.513 (2) |
N1—N2 | 1.3491 (17) | C4—C5 | 1.361 (2) |
N1—C2 | 1.3606 (17) | C4—C3 | 1.395 (2) |
N1—C7 | 1.4582 (17) | C4—H4 | 0.9300 |
C2—C3 | 1.3934 (18) | C1—C6 | 1.364 (2) |
C2—C1 | 1.396 (2) | C1—H1 | 0.9300 |
N3—N2 | 1.3006 (18) | C11—C12 | 1.386 (2) |
N3—C3 | 1.3739 (18) | C11—H11 | 0.9300 |
C14—C15 | 1.378 (2) | C6—C5 | 1.405 (2) |
C14—C13 | 1.387 (2) | C6—H6 | 0.9300 |
C14—H14 | 0.9300 | C5—H5 | 0.9300 |
C10—C15 | 1.3866 (19) | C16—C17 | 1.485 (3) |
C10—C11 | 1.387 (2) | C16—H16A | 0.9700 |
C10—C9 | 1.4880 (18) | C16—H16B | 0.9700 |
C8—C9 | 1.5046 (18) | C7—H7A | 0.9700 |
C8—C7 | 1.5058 (18) | C7—H7B | 0.9700 |
C8—H8A | 0.9700 | C12—H12 | 0.9300 |
C8—H8B | 0.9700 | C17—H17A | 0.9600 |
C15—H15 | 0.9300 | C17—H17B | 0.9600 |
C13—C12 | 1.385 (2) | C17—H17C | 0.9600 |
N2—N1—C2 | 110.20 (11) | C2—C1—H1 | 122.1 |
N2—N1—C7 | 119.33 (12) | N3—C3—C2 | 108.55 (12) |
C2—N1—C7 | 130.47 (13) | N3—C3—C4 | 130.56 (13) |
N1—C2—C3 | 104.00 (12) | C2—C3—C4 | 120.89 (13) |
N1—C2—C1 | 133.85 (13) | C12—C11—C10 | 120.41 (14) |
C3—C2—C1 | 122.16 (13) | C12—C11—H11 | 119.8 |
N2—N3—C3 | 108.09 (11) | C10—C11—H11 | 119.8 |
C15—C14—C13 | 121.01 (13) | C1—C6—C5 | 122.44 (15) |
C15—C14—H14 | 119.5 | C1—C6—H6 | 118.8 |
C13—C14—H14 | 119.5 | C5—C6—H6 | 118.8 |
N3—N2—N1 | 109.17 (11) | C4—C5—C6 | 121.71 (14) |
C15—C10—C11 | 118.26 (12) | C4—C5—H5 | 119.1 |
C15—C10—C9 | 119.27 (12) | C6—C5—H5 | 119.1 |
C11—C10—C9 | 122.46 (12) | C17—C16—C13 | 111.81 (15) |
C9—C8—C7 | 112.38 (11) | C17—C16—H16A | 109.3 |
C9—C8—H8A | 109.1 | C13—C16—H16A | 109.3 |
C7—C8—H8A | 109.1 | C17—C16—H16B | 109.3 |
C9—C8—H8B | 109.1 | C13—C16—H16B | 109.3 |
C7—C8—H8B | 109.1 | H16A—C16—H16B | 107.9 |
H8A—C8—H8B | 107.9 | N1—C7—C8 | 112.05 (12) |
O1—C9—C10 | 120.48 (13) | N1—C7—H7A | 109.2 |
O1—C9—C8 | 120.57 (12) | C8—C7—H7A | 109.2 |
C10—C9—C8 | 118.95 (11) | N1—C7—H7B | 109.2 |
C14—C15—C10 | 121.05 (13) | C8—C7—H7B | 109.2 |
C14—C15—H15 | 119.5 | H7A—C7—H7B | 107.9 |
C10—C15—H15 | 119.5 | C13—C12—C11 | 121.33 (15) |
C12—C13—C14 | 117.89 (13) | C13—C12—H12 | 119.3 |
C12—C13—C16 | 120.80 (15) | C11—C12—H12 | 119.3 |
C14—C13—C16 | 121.24 (15) | C16—C17—H17A | 109.5 |
C5—C4—C3 | 116.95 (14) | C16—C17—H17B | 109.5 |
C5—C4—H4 | 121.5 | H17A—C17—H17B | 109.5 |
C3—C4—H4 | 121.5 | C16—C17—H17C | 109.5 |
C6—C1—C2 | 115.85 (14) | H17A—C17—H17C | 109.5 |
C6—C1—H1 | 122.1 | H17B—C17—H17C | 109.5 |
N2—N1—C2—C3 | −0.01 (14) | N2—N3—C3—C4 | −179.29 (14) |
C7—N1—C2—C3 | 179.27 (13) | N1—C2—C3—N3 | −0.04 (14) |
N2—N1—C2—C1 | −179.61 (15) | C1—C2—C3—N3 | 179.62 (13) |
C7—N1—C2—C1 | −0.3 (2) | N1—C2—C3—C4 | 179.40 (12) |
C3—N3—N2—N1 | −0.08 (16) | C1—C2—C3—C4 | −0.9 (2) |
C2—N1—N2—N3 | 0.05 (16) | C5—C4—C3—N3 | 179.43 (14) |
C7—N1—N2—N3 | −179.32 (12) | C5—C4—C3—C2 | 0.1 (2) |
C15—C10—C9—O1 | 15.1 (2) | C15—C10—C11—C12 | 0.1 (2) |
C11—C10—C9—O1 | −165.09 (16) | C9—C10—C11—C12 | −179.69 (14) |
C15—C10—C9—C8 | −164.43 (13) | C2—C1—C6—C5 | −0.3 (2) |
C11—C10—C9—C8 | 15.4 (2) | C3—C4—C5—C6 | 0.5 (2) |
C7—C8—C9—O1 | −5.6 (2) | C1—C6—C5—C4 | −0.5 (3) |
C7—C8—C9—C10 | 173.93 (13) | C12—C13—C16—C17 | 75.6 (2) |
C13—C14—C15—C10 | 0.6 (2) | C14—C13—C16—C17 | −101.4 (2) |
C11—C10—C15—C14 | −1.1 (2) | N2—N1—C7—C8 | −71.69 (17) |
C9—C10—C15—C14 | 178.70 (13) | C2—N1—C7—C8 | 109.09 (16) |
C15—C14—C13—C12 | 1.0 (2) | C9—C8—C7—N1 | −177.86 (12) |
C15—C14—C13—C16 | 178.11 (14) | C14—C13—C12—C11 | −2.0 (2) |
N1—C2—C1—C6 | −179.46 (14) | C16—C13—C12—C11 | −179.12 (15) |
C3—C2—C1—C6 | 1.0 (2) | C10—C11—C12—C13 | 1.5 (3) |
N2—N3—C3—C2 | 0.07 (16) |
D—H···A | D—H | H···A | D···A | D—H···A |
C4—H4···O1i | 0.93 | 2.55 | 3.310 (2) | 139 |
Symmetry code: (i) −x+1, y−1/2, −z+3/2. |
Experimental details
Crystal data | |
Chemical formula | C17H17N3O |
Mr | 279.34 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 293 |
a, b, c (Å) | 5.7577 (5), 13.9599 (12), 18.6746 (17) |
β (°) | 98.585 (5) |
V (Å3) | 1484.2 (2) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.08 |
Crystal size (mm) | 0.22 × 0.2 × 0.1 |
Data collection | |
Diffractometer | Bruker SMART CCD area-detector |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.983, 0.99 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 15817, 2918, 2410 |
Rint | 0.020 |
(sin θ/λ)max (Å−1) | 0.617 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.041, 0.116, 1.05 |
No. of reflections | 2918 |
No. of parameters | 190 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.20, −0.15 |
Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), 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 | 2.55 | 3.310 (2) | 139 |
Symmetry code: (i) −x+1, y−1/2, −z+3/2. |
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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 structure of the title compound (Fig. 1) as part of our ongoing studies of new benzotriazole compounds with potential bioactivity.
All bond lengths and angles are within normal ranges (Allen et al., 1987). The benzotriazole fused rings system is essentially planar, with a dihedral angle of 0.52 (8)° between the triazole ring (atoms N1—N3/C1/C6) and the benzene ring (C1—C6). The mean plane of the benzotriazole moiety and the benzene ring (C10—C15) make a dihedral angle of 70.50 (6)°. The crystal structure (Fig. 2) is stabilized by weak C—H···O interactions and Van der Waals interactions.