Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807026566/hk2263sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807026566/hk2263Isup2.hkl |
CCDC reference: 654867
The title compound was prepared according to the literature method (Wang et al., 2005). Single crystals suitable for X-ray diffracion were obtained by slow evaporation of an ethyl acetate solution at room temperature over a period of 5 d.
H atoms were positioned geometrically, with C—H = 0.93 and 0.96 Å for aromatic and methylene H atoms, respectively, and constrained to ride on their parent atoms, with Uiso(H) = 1.2Ueq(C).
Recently we have reported the structure of 2-(2H-benzotriazol-2-yl)-1 -phenylethanone (Wang et al., 2005). As part of our ongoing studies on new benzotriazole derivatives with higher anti-inflammatory properties, the title compound, (I), was synthesized and we herein report its crystal structure.
In the molecule of the title compound, (I), (Fig. 1), the bond lengths and angles are within normal ranges (Allen et al., 1987). The benzotriazole system is essentially planar, with a dihedral angle of 0.13 (1)° between the planar rings A (C16—C21) and B (N1—N3/C16/C21). The dihedral angles between the nearly planar benzotriazole ring system and planar rings C (C7—C12) and D (C1—C6) are 58.52 (1)° and 77.16 (1)°, respectively. The rings C and D are oriented at a dihedral angle of 30.73 (1)°.
In the crystal structure, intermolecular C—H···N hydrogen bonds (Table 1) link the molecules into centrosymmetric dimers (Fig. 2), in which they may be effective in the stabilization of the structure.
For general background, see: Allen et al. (1987). For related literature, see: Wang et al. (2005).
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, 1999); software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003).
C21H17N3O | F(000) = 688 |
Mr = 327.38 | Dx = 1.259 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 1501 reflections |
a = 13.313 (3) Å | θ = 2.6–21.5° |
b = 10.661 (3) Å | µ = 0.08 mm−1 |
c = 13.629 (3) Å | T = 294 K |
β = 116.739 (4)° | Needle, colorless |
V = 1727.5 (7) Å3 | 0.43 × 0.13 × 0.06 mm |
Z = 4 |
Siemens SMART 1000 CCD area-detector diffractometer | 3259 independent reflections |
Radiation source: fine-focus sealed tube | 2061 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.032 |
Detector resolution: 8.33 pixels mm-1 | θmax = 25.7°, θmin = 1.7° |
ω scans | h = −11→16 |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | k = −13→12 |
Tmin = 0.967, Tmax = 0.995 | l = −16→13 |
9149 measured reflections |
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)] = 0.053 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.125 | H-atom parameters constrained |
S = 1.06 | w = 1/[σ2(Fo2) + (0.0491P)2 + 0.0564P] where P = (Fo2 + 2Fc2)/3 |
3259 reflections | (Δ/σ)max < 0.001 |
226 parameters | Δρmax = 0.12 e Å−3 |
0 restraints | Δρmin = −0.14 e Å−3 |
C21H17N3O | V = 1727.5 (7) Å3 |
Mr = 327.38 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 13.313 (3) Å | µ = 0.08 mm−1 |
b = 10.661 (3) Å | T = 294 K |
c = 13.629 (3) Å | 0.43 × 0.13 × 0.06 mm |
β = 116.739 (4)° |
Siemens SMART 1000 CCD area-detector diffractometer | 3259 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 2061 reflections with I > 2σ(I) |
Tmin = 0.967, Tmax = 0.995 | Rint = 0.032 |
9149 measured reflections |
R[F2 > 2σ(F2)] = 0.053 | 0 restraints |
wR(F2) = 0.125 | H-atom parameters constrained |
S = 1.06 | Δρmax = 0.12 e Å−3 |
3259 reflections | Δρmin = −0.14 e Å−3 |
226 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 | 0.55783 (13) | −0.10605 (15) | 0.30143 (12) | 0.0812 (5) | |
N1 | 0.35490 (14) | 0.09972 (16) | −0.06672 (13) | 0.0606 (5) | |
N2 | 0.33680 (13) | 0.07937 (15) | 0.02037 (13) | 0.0574 (4) | |
N3 | 0.24092 (14) | 0.12146 (17) | 0.01559 (14) | 0.0665 (5) | |
C1 | 0.79900 (17) | 0.1402 (2) | 0.84539 (16) | 0.0695 (6) | |
H1B | 0.7912 | 0.0536 | 0.8374 | 0.083* | |
C2 | 0.85160 (18) | 0.1910 (3) | 0.94937 (17) | 0.0778 (7) | |
H2A | 0.8774 | 0.1386 | 1.0104 | 0.093* | |
C3 | 0.86613 (19) | 0.3174 (3) | 0.96371 (18) | 0.0820 (7) | |
H3B | 0.9021 | 0.3513 | 1.0340 | 0.098* | |
C4 | 0.8269 (2) | 0.3943 (2) | 0.87297 (19) | 0.0885 (8) | |
H4A | 0.8365 | 0.4807 | 0.8818 | 0.106* | |
C5 | 0.77336 (19) | 0.3433 (2) | 0.76876 (18) | 0.0771 (7) | |
H5A | 0.7474 | 0.3963 | 0.7081 | 0.093* | |
C6 | 0.75742 (16) | 0.2154 (2) | 0.75232 (16) | 0.0594 (5) | |
C7 | 0.69832 (16) | 0.1610 (2) | 0.64056 (15) | 0.0572 (5) | |
C8 | 0.61326 (17) | 0.2260 (2) | 0.55468 (16) | 0.0629 (6) | |
H8A | 0.5921 | 0.3049 | 0.5679 | 0.076* | |
C9 | 0.55970 (17) | 0.1758 (2) | 0.45025 (16) | 0.0615 (6) | |
H9A | 0.5041 | 0.2219 | 0.3941 | 0.074* | |
C10 | 0.58771 (16) | 0.05743 (19) | 0.42801 (16) | 0.0550 (5) | |
C11 | 0.67031 (19) | −0.0089 (2) | 0.51349 (18) | 0.0695 (6) | |
H11A | 0.6892 | −0.0892 | 0.5006 | 0.083* | |
C12 | 0.72515 (19) | 0.0418 (2) | 0.61747 (17) | 0.0707 (6) | |
H12A | 0.7811 | −0.0043 | 0.6732 | 0.085* | |
C13 | 0.53522 (17) | 0.0009 (2) | 0.31687 (17) | 0.0590 (5) | |
C14 | 0.45417 (17) | 0.07756 (19) | 0.22105 (14) | 0.0618 (6) | |
H14A | 0.4900 | 0.1555 | 0.2176 | 0.074* | |
H14B | 0.3889 | 0.0980 | 0.2319 | 0.074* | |
C15 | 0.41685 (17) | 0.00770 (19) | 0.11401 (15) | 0.0600 (5) | |
H15A | 0.4822 | −0.0116 | 0.1029 | 0.072* | |
H15B | 0.3825 | −0.0710 | 0.1183 | 0.072* | |
C16 | 0.26081 (17) | 0.16226 (19) | −0.13612 (15) | 0.0543 (5) | |
C17 | 0.22998 (18) | 0.2101 (2) | −0.24210 (16) | 0.0661 (6) | |
H17A | 0.2765 | 0.2018 | −0.2762 | 0.079* | |
C18 | 0.1295 (2) | 0.2687 (2) | −0.29181 (17) | 0.0703 (6) | |
H18A | 0.1064 | 0.3010 | −0.3621 | 0.084* | |
C19 | 0.05804 (19) | 0.2828 (2) | −0.24106 (19) | 0.0817 (7) | |
H19A | −0.0104 | 0.3239 | −0.2788 | 0.098* | |
C20 | 0.08668 (19) | 0.2378 (2) | −0.13857 (19) | 0.0810 (7) | |
H20A | 0.0397 | 0.2478 | −0.1052 | 0.097* | |
C21 | 0.19040 (17) | 0.1756 (2) | −0.08537 (16) | 0.0597 (5) |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0986 (12) | 0.0610 (10) | 0.0841 (10) | 0.0134 (9) | 0.0412 (9) | −0.0008 (8) |
N1 | 0.0585 (11) | 0.0736 (12) | 0.0594 (10) | −0.0082 (9) | 0.0351 (9) | −0.0082 (9) |
N2 | 0.0525 (11) | 0.0679 (12) | 0.0571 (10) | −0.0043 (8) | 0.0293 (9) | −0.0063 (8) |
N3 | 0.0532 (11) | 0.0909 (14) | 0.0656 (11) | 0.0038 (10) | 0.0359 (9) | 0.0010 (9) |
C1 | 0.0594 (14) | 0.0866 (17) | 0.0596 (14) | −0.0049 (12) | 0.0242 (11) | 0.0152 (12) |
C2 | 0.0593 (15) | 0.111 (2) | 0.0594 (15) | −0.0005 (14) | 0.0233 (12) | 0.0180 (14) |
C3 | 0.0654 (16) | 0.114 (2) | 0.0615 (15) | 0.0160 (15) | 0.0238 (12) | −0.0047 (15) |
C4 | 0.0904 (19) | 0.0851 (19) | 0.0749 (17) | 0.0225 (14) | 0.0239 (15) | −0.0023 (14) |
C5 | 0.0817 (17) | 0.0790 (18) | 0.0615 (14) | 0.0207 (13) | 0.0242 (13) | 0.0091 (12) |
C6 | 0.0499 (13) | 0.0743 (16) | 0.0558 (13) | 0.0069 (11) | 0.0253 (10) | 0.0095 (11) |
C7 | 0.0530 (13) | 0.0676 (15) | 0.0559 (12) | 0.0074 (11) | 0.0287 (10) | 0.0151 (10) |
C8 | 0.0616 (14) | 0.0674 (14) | 0.0587 (13) | 0.0142 (11) | 0.0260 (11) | 0.0041 (11) |
C9 | 0.0563 (13) | 0.0694 (15) | 0.0567 (12) | 0.0135 (11) | 0.0236 (10) | 0.0096 (11) |
C10 | 0.0542 (13) | 0.0543 (13) | 0.0626 (13) | 0.0042 (10) | 0.0316 (11) | 0.0086 (10) |
C11 | 0.0799 (17) | 0.0571 (14) | 0.0724 (15) | 0.0127 (12) | 0.0351 (13) | 0.0114 (11) |
C12 | 0.0732 (16) | 0.0695 (16) | 0.0658 (15) | 0.0193 (12) | 0.0281 (12) | 0.0222 (12) |
C13 | 0.0580 (14) | 0.0565 (14) | 0.0725 (14) | 0.0006 (11) | 0.0382 (12) | 0.0032 (11) |
C14 | 0.0624 (14) | 0.0616 (14) | 0.0638 (13) | 0.0015 (10) | 0.0305 (11) | −0.0027 (10) |
C15 | 0.0571 (13) | 0.0639 (14) | 0.0656 (13) | 0.0001 (10) | 0.0336 (11) | −0.0012 (11) |
C16 | 0.0496 (12) | 0.0627 (13) | 0.0538 (12) | −0.0103 (10) | 0.0262 (10) | −0.0117 (10) |
C17 | 0.0610 (15) | 0.0825 (16) | 0.0598 (13) | −0.0152 (12) | 0.0318 (12) | −0.0128 (11) |
C18 | 0.0637 (16) | 0.0892 (17) | 0.0538 (13) | −0.0132 (13) | 0.0226 (12) | −0.0072 (11) |
C19 | 0.0549 (15) | 0.114 (2) | 0.0686 (15) | 0.0011 (13) | 0.0209 (12) | 0.0015 (14) |
C20 | 0.0594 (15) | 0.120 (2) | 0.0724 (16) | 0.0075 (14) | 0.0372 (13) | 0.0055 (14) |
C21 | 0.0488 (13) | 0.0769 (15) | 0.0561 (12) | −0.0071 (11) | 0.0260 (11) | −0.0037 (11) |
N1—C16 | 1.357 (2) | C10—C11 | 1.384 (3) |
N2—N1 | 1.3309 (19) | C11—H11A | 0.9300 |
N2—N3 | 1.327 (2) | C12—C11 | 1.380 (3) |
N2—C15 | 1.458 (2) | C12—H12A | 0.9300 |
N3—C21 | 1.359 (2) | C13—O1 | 1.222 (2) |
C1—C2 | 1.378 (3) | C13—C10 | 1.481 (3) |
C1—H1B | 0.9300 | C13—C14 | 1.506 (3) |
C2—C3 | 1.362 (3) | C14—C15 | 1.509 (2) |
C2—H2A | 0.9300 | C14—H14A | 0.9700 |
C3—H3B | 0.9300 | C14—H14B | 0.9700 |
C4—C3 | 1.376 (3) | C15—H15A | 0.9700 |
C4—C5 | 1.382 (3) | C15—H15B | 0.9700 |
C4—H4A | 0.9300 | C16—C17 | 1.408 (3) |
C5—H5A | 0.9300 | C16—C21 | 1.400 (3) |
C6—C1 | 1.388 (3) | C17—H17A | 0.9300 |
C6—C5 | 1.382 (3) | C18—C17 | 1.350 (3) |
C7—C6 | 1.482 (3) | C18—C19 | 1.413 (3) |
C7—C12 | 1.393 (3) | C18—H18A | 0.9300 |
C8—C7 | 1.393 (3) | C19—H19A | 0.9300 |
C8—H8A | 0.9300 | C20—C19 | 1.359 (3) |
C9—C8 | 1.381 (3) | C20—H20A | 0.9300 |
C9—C10 | 1.387 (3) | C21—C20 | 1.404 (3) |
C9—H9A | 0.9300 | ||
N2—N1—C16 | 102.77 (15) | C10—C11—H11A | 119.4 |
N3—N2—N1 | 117.21 (16) | C11—C12—C7 | 121.25 (19) |
N3—N2—C15 | 121.91 (16) | C11—C12—H12A | 119.4 |
N1—N2—C15 | 120.80 (16) | C7—C12—H12A | 119.4 |
N2—N3—C21 | 102.73 (16) | O1—C13—C10 | 121.09 (19) |
C2—C1—C6 | 121.4 (2) | O1—C13—C14 | 119.52 (19) |
C2—C1—H1B | 119.3 | C10—C13—C14 | 119.37 (18) |
C6—C1—H1B | 119.3 | C13—C14—C15 | 111.48 (17) |
C3—C2—C1 | 120.7 (2) | C13—C14—H14A | 109.3 |
C3—C2—H2A | 119.7 | C15—C14—H14A | 109.3 |
C1—C2—H2A | 119.7 | C13—C14—H14B | 109.3 |
C2—C3—C4 | 119.2 (2) | C15—C14—H14B | 109.3 |
C2—C3—H3B | 120.4 | H14A—C14—H14B | 108.0 |
C4—C3—H3B | 120.4 | N2—C15—C14 | 112.38 (16) |
C3—C4—C5 | 120.0 (2) | N2—C15—H15A | 109.1 |
C3—C4—H4A | 120.0 | C14—C15—H15A | 109.1 |
C5—C4—H4A | 120.0 | N2—C15—H15B | 109.1 |
C4—C5—C6 | 121.7 (2) | C14—C15—H15B | 109.1 |
C4—C5—H5A | 119.2 | H15A—C15—H15B | 107.9 |
C6—C5—H5A | 119.2 | N1—C16—C21 | 108.58 (17) |
C5—C6—C1 | 116.91 (19) | N1—C16—C17 | 130.15 (18) |
C5—C6—C7 | 121.63 (18) | C21—C16—C17 | 121.3 (2) |
C1—C6—C7 | 121.5 (2) | C18—C17—C16 | 116.6 (2) |
C8—C7—C12 | 117.25 (19) | C18—C17—H17A | 121.7 |
C8—C7—C6 | 121.58 (19) | C16—C17—H17A | 121.7 |
C12—C7—C6 | 121.17 (18) | C17—C18—C19 | 122.4 (2) |
C9—C8—C7 | 121.4 (2) | C17—C18—H18A | 118.8 |
C9—C8—H8A | 119.3 | C19—C18—H18A | 118.8 |
C7—C8—H8A | 119.3 | C20—C19—C18 | 121.7 (2) |
C8—C9—C10 | 120.86 (19) | C20—C19—H19A | 119.1 |
C8—C9—H9A | 119.6 | C18—C19—H19A | 119.1 |
C10—C9—H9A | 119.6 | C19—C20—C21 | 117.0 (2) |
C11—C10—C9 | 118.09 (19) | C19—C20—H20A | 121.5 |
C11—C10—C13 | 118.94 (19) | C21—C20—H20A | 121.5 |
C9—C10—C13 | 122.95 (18) | N3—C21—C16 | 108.71 (19) |
C12—C11—C10 | 121.1 (2) | N3—C21—C20 | 130.34 (19) |
C12—C11—H11A | 119.4 | C16—C21—C20 | 120.95 (19) |
N2—N1—C16—C21 | −0.1 (2) | C9—C8—C7—C6 | 178.93 (18) |
N2—N1—C16—C17 | 179.73 (19) | C10—C9—C8—C7 | 1.2 (3) |
N1—N2—N3—C21 | −0.1 (2) | C8—C9—C10—C11 | 0.4 (3) |
C15—N2—N3—C21 | −176.82 (17) | C8—C9—C10—C13 | −178.14 (18) |
N3—N2—N1—C16 | 0.2 (2) | C9—C10—C11—C12 | −1.4 (3) |
C15—N2—N1—C16 | 176.90 (16) | C13—C10—C11—C12 | 177.18 (19) |
N3—N2—C15—C14 | −56.8 (2) | C7—C12—C11—C10 | 0.9 (3) |
N1—N2—C15—C14 | 126.62 (17) | O1—C13—C14—C15 | −3.4 (3) |
N2—N3—C21—C16 | 0.0 (2) | C10—C13—C14—C15 | 175.54 (17) |
N2—N3—C21—C20 | −179.5 (2) | O1—C13—C10—C11 | 5.3 (3) |
C6—C1—C2—C3 | −1.2 (3) | C14—C13—C10—C11 | −173.63 (18) |
C1—C2—C3—C4 | 0.4 (3) | O1—C13—C10—C9 | −176.23 (19) |
C5—C4—C3—C2 | 0.1 (4) | C14—C13—C10—C9 | 4.9 (3) |
C3—C4—C5—C6 | 0.1 (4) | C13—C14—C15—N2 | 179.00 (16) |
C5—C6—C1—C2 | 1.3 (3) | N1—C16—C17—C18 | 179.9 (2) |
C7—C6—C1—C2 | −178.46 (19) | C21—C16—C17—C18 | −0.2 (3) |
C1—C6—C5—C4 | −0.8 (3) | N1—C16—C21—N3 | 0.1 (2) |
C7—C6—C5—C4 | 179.0 (2) | C17—C16—C21—N3 | −179.81 (18) |
C8—C7—C6—C5 | −31.0 (3) | N1—C16—C21—C20 | 179.63 (19) |
C12—C7—C6—C5 | 149.5 (2) | C17—C16—C21—C20 | −0.2 (3) |
C8—C7—C6—C1 | 148.8 (2) | C19—C18—C17—C16 | 0.3 (3) |
C12—C7—C6—C1 | −30.7 (3) | C17—C18—C19—C20 | 0.0 (4) |
C8—C7—C12—C11 | 0.6 (3) | C21—C20—C19—C18 | −0.5 (4) |
C6—C7—C12—C11 | −179.95 (19) | N3—C21—C20—C19 | −180.0 (2) |
C9—C8—C7—C12 | −1.6 (3) | C16—C21—C20—C19 | 0.6 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
C15—H15A···N1i | 0.96 | 2.61 | 3.567 (3) | 171 |
Symmetry code: (i) −x+1, −y, −z. |
Experimental details
Crystal data | |
Chemical formula | C21H17N3O |
Mr | 327.38 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 294 |
a, b, c (Å) | 13.313 (3), 10.661 (3), 13.629 (3) |
β (°) | 116.739 (4) |
V (Å3) | 1727.5 (7) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.08 |
Crystal size (mm) | 0.43 × 0.13 × 0.06 |
Data collection | |
Diffractometer | Siemens SMART 1000 CCD area-detector |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.967, 0.995 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 9149, 3259, 2061 |
Rint | 0.032 |
(sin θ/λ)max (Å−1) | 0.609 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.053, 0.125, 1.06 |
No. of reflections | 3259 |
No. of parameters | 226 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.12, −0.14 |
Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1999), SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003).
D—H···A | D—H | H···A | D···A | D—H···A |
C15—H15A···N1i | 0.96 | 2.61 | 3.567 (3) | 170.86 |
Symmetry code: (i) −x+1, −y, −z. |
Recently we have reported the structure of 2-(2H-benzotriazol-2-yl)-1 -phenylethanone (Wang et al., 2005). As part of our ongoing studies on new benzotriazole derivatives with higher anti-inflammatory properties, the title compound, (I), was synthesized and we herein report its crystal structure.
In the molecule of the title compound, (I), (Fig. 1), the bond lengths and angles are within normal ranges (Allen et al., 1987). The benzotriazole system is essentially planar, with a dihedral angle of 0.13 (1)° between the planar rings A (C16—C21) and B (N1—N3/C16/C21). The dihedral angles between the nearly planar benzotriazole ring system and planar rings C (C7—C12) and D (C1—C6) are 58.52 (1)° and 77.16 (1)°, respectively. The rings C and D are oriented at a dihedral angle of 30.73 (1)°.
In the crystal structure, intermolecular C—H···N hydrogen bonds (Table 1) link the molecules into centrosymmetric dimers (Fig. 2), in which they may be effective in the stabilization of the structure.