Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807053251/hk2350sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807053251/hk2350Isup2.hkl |
CCDC reference: 636550
The title compound was prepared according to the literature method (Wan et al., 2007). Single crystals suitable for X-ray analysis were obtained by slow evaporation of an ethyl acetate solution at room temperature over a period of 6 d.
H atoms were positioned geometrically with C—H = 0.93, 0.98 and 0.97 Å for aromatic, methine and methylene H atoms, respectively, and constrained to ride on their parent atoms, with Uiso(H) = 1.2Ueq(C).
We have recently reported the structure of 3-(1H-Benzotriazol-1-yl)-1 -(2-fluorobenzoyl)ethyl nicotinate, (II), (Wan et al., 2007). As part of our ongoing studies to search for benzotriazole derivatives with higher pharmacological activities, such as antifungal, antitumor and antineoplastic, the title compound (I) was synthesized and its crystal structure is reported here.
In the molecule of the title compound, (I), (Fig. 1) the bond lengths and angles are generally within normal ranges (Allen et al., 1987), and are comparable to those in the related compound (II). In (I), the benzotriazole group is essentially planar, with a dihedral angle of 0.99 (1)° between triazole A (N1—N3/C10/C11) and benzene B (C10—C15) rings. Rings C (C1—C6) and D (C17—C22) are oriented with respect to the benzotriazole system at dihedral angles of 3.22 (1) and 86.48 (1)°, respectively, while the dihedral angle between them is 88.08 (1)°. The intramolecular C—H···F hydrogen bond (Table 1) results in the formation of a six-membered ring E (F1/C1/C6—C8/H8A) (Fig. 1).
In the crystal structure, intermolecular C—H···O hydrogen bonds (Table 1), link the molecules into centrosymmetric dimers (Fig. 2). The packing is further stabilized by π-π interactions involving the C rings with centroid-centroid distance of 3.601 (2) Å (symmetry code: 1 - x, -y, -z).
For related literature, see: Wan et al., (2007). For bond-length data, see: Allen et al. (1987).
Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL (Sheldrick, 1997b), PARST (Nardelli, 1995) and PLATON (Spek, 2003).
C22H16FN3O3 | Z = 2 |
Mr = 389.38 | F(000) = 404 |
Triclinic, P1 | Dx = 1.387 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 9.8372 (11) Å | Cell parameters from 1186 reflections |
b = 9.8985 (12) Å | θ = 2.3–24.9° |
c = 11.6126 (13) Å | µ = 0.10 mm−1 |
α = 115.187 (2)° | T = 294 K |
β = 101.572 (2)° | Block, colorless |
γ = 103.929 (2)° | 0.32 × 0.25 × 0.10 mm |
V = 932.17 (19) Å3 |
Siemens SMART 1000 CCD area-detector diffractometer | 3612 independent reflections |
Radiation source: fine-focus sealed tube | 2543 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.019 |
Detector resolution: 8.33 pixels mm-1 | θmax = 26.0°, θmin = 2.1° |
ω scans | h = −12→6 |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | k = −11→12 |
Tmin = 0.968, Tmax = 0.990 | l = −14→14 |
5309 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) = 0.118 | H-atom parameters constrained |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0399P)2 + 0.1753P] where P = (Fo2 + 2Fc2)/3 |
3612 reflections | (Δ/σ)max < 0.001 |
262 parameters | Δρmax = 0.14 e Å−3 |
0 restraints | Δρmin = −0.21 e Å−3 |
C22H16FN3O3 | γ = 103.929 (2)° |
Mr = 389.38 | V = 932.17 (19) Å3 |
Triclinic, P1 | Z = 2 |
a = 9.8372 (11) Å | Mo Kα radiation |
b = 9.8985 (12) Å | µ = 0.10 mm−1 |
c = 11.6126 (13) Å | T = 294 K |
α = 115.187 (2)° | 0.32 × 0.25 × 0.10 mm |
β = 101.572 (2)° |
Siemens SMART 1000 CCD area-detector diffractometer | 3612 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 2543 reflections with I > 2σ(I) |
Tmin = 0.968, Tmax = 0.990 | Rint = 0.019 |
5309 measured reflections |
R[F2 > 2σ(F2)] = 0.053 | 0 restraints |
wR(F2) = 0.118 | H-atom parameters constrained |
S = 1.04 | Δρmax = 0.14 e Å−3 |
3612 reflections | Δρmin = −0.21 e Å−3 |
262 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 | ||
F1 | 0.60239 (17) | 0.34447 (16) | 0.07729 (12) | 0.0707 (4) | |
O1 | 0.84080 (18) | 0.27597 (19) | 0.37136 (14) | 0.0602 (5) | |
O2 | 0.77177 (15) | 0.52712 (15) | 0.49177 (12) | 0.0436 (4) | |
O3 | 0.55363 (18) | 0.34154 (19) | 0.44232 (15) | 0.0614 (5) | |
N1 | 0.80939 (19) | 0.72821 (19) | 0.36119 (16) | 0.0410 (4) | |
N2 | 0.7254 (2) | 0.7301 (2) | 0.25404 (17) | 0.0536 (5) | |
N3 | 0.6900 (2) | 0.8564 (2) | 0.2985 (2) | 0.0589 (5) | |
C1 | 0.6462 (2) | 0.2172 (2) | 0.0430 (2) | 0.0443 (5) | |
C2 | 0.6046 (3) | 0.1115 (3) | −0.0929 (2) | 0.0562 (6) | |
H2B | 0.5498 | 0.1285 | −0.1572 | 0.067* | |
C3 | 0.6455 (3) | −0.0192 (3) | −0.1316 (2) | 0.0629 (7) | |
H3B | 0.6199 | −0.0913 | −0.2232 | 0.076* | |
C4 | 0.7243 (3) | −0.0447 (3) | −0.0359 (3) | 0.0650 (7) | |
H4A | 0.7508 | −0.1345 | −0.0628 | 0.078* | |
C5 | 0.7640 (2) | 0.0628 (3) | 0.0997 (2) | 0.0535 (6) | |
H5A | 0.8171 | 0.0440 | 0.1635 | 0.064* | |
C6 | 0.7269 (2) | 0.1990 (2) | 0.14382 (19) | 0.0394 (5) | |
C7 | 0.7744 (2) | 0.3082 (2) | 0.2927 (2) | 0.0400 (5) | |
C8 | 0.7447 (2) | 0.4643 (2) | 0.34929 (18) | 0.0393 (5) | |
H8A | 0.6418 | 0.4454 | 0.3018 | 0.047* | |
C9 | 0.8546 (2) | 0.5926 (2) | 0.3385 (2) | 0.0429 (5) | |
H9A | 0.9523 | 0.6300 | 0.4046 | 0.051* | |
H9B | 0.8627 | 0.5455 | 0.2491 | 0.051* | |
C10 | 0.8278 (2) | 0.8585 (2) | 0.4790 (2) | 0.0404 (5) | |
C11 | 0.7505 (2) | 0.9393 (3) | 0.4378 (2) | 0.0478 (5) | |
C12 | 0.7438 (3) | 1.0812 (3) | 0.5334 (3) | 0.0659 (7) | |
H12A | 0.6908 | 1.1357 | 0.5074 | 0.079* | |
C13 | 0.8184 (3) | 1.1363 (3) | 0.6665 (3) | 0.0704 (8) | |
H13A | 0.8162 | 1.2303 | 0.7326 | 0.084* | |
C14 | 0.8982 (3) | 1.0544 (3) | 0.7057 (2) | 0.0656 (7) | |
H14A | 0.9486 | 1.0969 | 0.7975 | 0.079* | |
C15 | 0.9049 (3) | 0.9151 (3) | 0.6149 (2) | 0.0517 (6) | |
H15A | 0.9577 | 0.8610 | 0.6419 | 0.062* | |
C16 | 0.6693 (2) | 0.4465 (2) | 0.5249 (2) | 0.0411 (5) | |
C17 | 0.7187 (2) | 0.5001 (2) | 0.67165 (19) | 0.0389 (5) | |
C18 | 0.6172 (3) | 0.4414 (3) | 0.7218 (2) | 0.0485 (5) | |
H18A | 0.5200 | 0.3731 | 0.6644 | 0.058* | |
C19 | 0.6600 (3) | 0.4842 (3) | 0.8570 (2) | 0.0563 (6) | |
H19A | 0.5907 | 0.4474 | 0.8911 | 0.068* | |
C20 | 0.8046 (3) | 0.5809 (3) | 0.9413 (2) | 0.0594 (7) | |
H20A | 0.8335 | 0.6077 | 1.0320 | 0.071* | |
C21 | 0.9073 (3) | 0.6385 (3) | 0.8918 (2) | 0.0591 (7) | |
H21A | 1.0054 | 0.7031 | 0.9487 | 0.071* | |
C22 | 0.8637 (2) | 0.5997 (3) | 0.7575 (2) | 0.0477 (6) | |
H22A | 0.9320 | 0.6407 | 0.7247 | 0.057* |
U11 | U22 | U33 | U12 | U13 | U23 | |
F1 | 0.1010 (12) | 0.0678 (9) | 0.0465 (8) | 0.0491 (9) | 0.0129 (8) | 0.0272 (7) |
O1 | 0.0772 (12) | 0.0693 (11) | 0.0448 (9) | 0.0394 (9) | 0.0157 (8) | 0.0333 (8) |
O2 | 0.0501 (9) | 0.0428 (8) | 0.0305 (7) | 0.0095 (7) | 0.0149 (7) | 0.0156 (6) |
O3 | 0.0550 (10) | 0.0615 (10) | 0.0442 (9) | 0.0003 (9) | 0.0100 (8) | 0.0208 (8) |
N1 | 0.0481 (11) | 0.0417 (10) | 0.0349 (9) | 0.0158 (8) | 0.0115 (8) | 0.0221 (8) |
N2 | 0.0615 (13) | 0.0555 (12) | 0.0443 (11) | 0.0163 (10) | 0.0099 (10) | 0.0318 (10) |
N3 | 0.0670 (14) | 0.0561 (12) | 0.0607 (13) | 0.0234 (11) | 0.0135 (11) | 0.0385 (11) |
C1 | 0.0469 (13) | 0.0430 (12) | 0.0423 (12) | 0.0176 (10) | 0.0144 (10) | 0.0206 (10) |
C2 | 0.0612 (16) | 0.0571 (15) | 0.0354 (12) | 0.0134 (12) | 0.0077 (11) | 0.0189 (11) |
C3 | 0.0614 (17) | 0.0551 (15) | 0.0396 (13) | 0.0076 (13) | 0.0142 (12) | 0.0048 (12) |
C4 | 0.0663 (17) | 0.0458 (14) | 0.0617 (16) | 0.0232 (13) | 0.0176 (14) | 0.0097 (12) |
C5 | 0.0505 (14) | 0.0485 (13) | 0.0527 (14) | 0.0200 (11) | 0.0102 (11) | 0.0202 (11) |
C6 | 0.0392 (12) | 0.0393 (11) | 0.0360 (11) | 0.0121 (9) | 0.0124 (10) | 0.0172 (9) |
C7 | 0.0398 (12) | 0.0466 (12) | 0.0384 (11) | 0.0155 (10) | 0.0141 (10) | 0.0250 (10) |
C8 | 0.0455 (13) | 0.0423 (11) | 0.0283 (10) | 0.0165 (10) | 0.0113 (9) | 0.0165 (9) |
C9 | 0.0496 (13) | 0.0453 (12) | 0.0383 (11) | 0.0206 (10) | 0.0180 (10) | 0.0218 (10) |
C10 | 0.0432 (13) | 0.0375 (11) | 0.0416 (12) | 0.0126 (9) | 0.0158 (10) | 0.0214 (10) |
C11 | 0.0514 (14) | 0.0443 (12) | 0.0546 (14) | 0.0170 (11) | 0.0182 (12) | 0.0307 (11) |
C12 | 0.0767 (19) | 0.0538 (15) | 0.089 (2) | 0.0355 (14) | 0.0374 (17) | 0.0444 (15) |
C13 | 0.095 (2) | 0.0457 (14) | 0.0719 (18) | 0.0292 (14) | 0.0408 (17) | 0.0230 (13) |
C14 | 0.085 (2) | 0.0522 (15) | 0.0460 (14) | 0.0197 (14) | 0.0195 (14) | 0.0173 (12) |
C15 | 0.0594 (15) | 0.0481 (13) | 0.0426 (13) | 0.0196 (11) | 0.0128 (11) | 0.0206 (11) |
C16 | 0.0450 (13) | 0.0389 (11) | 0.0394 (12) | 0.0164 (10) | 0.0160 (11) | 0.0184 (10) |
C17 | 0.0471 (13) | 0.0373 (11) | 0.0368 (11) | 0.0195 (10) | 0.0193 (10) | 0.0180 (9) |
C18 | 0.0496 (14) | 0.0516 (13) | 0.0489 (13) | 0.0172 (11) | 0.0212 (11) | 0.0278 (11) |
C19 | 0.0693 (17) | 0.0629 (15) | 0.0532 (14) | 0.0263 (13) | 0.0347 (13) | 0.0360 (13) |
C20 | 0.0771 (19) | 0.0663 (16) | 0.0370 (12) | 0.0259 (14) | 0.0235 (13) | 0.0262 (12) |
C21 | 0.0568 (16) | 0.0672 (16) | 0.0402 (13) | 0.0143 (13) | 0.0119 (12) | 0.0223 (12) |
C22 | 0.0501 (14) | 0.0516 (13) | 0.0416 (12) | 0.0162 (11) | 0.0214 (11) | 0.0223 (11) |
O2—C16 | 1.352 (2) | C22—C21 | 1.380 (3) |
O2—C8 | 1.436 (2) | C22—H22A | 0.9300 |
F1—C1 | 1.354 (2) | C18—C19 | 1.380 (3) |
O3—C16 | 1.200 (2) | C18—H18A | 0.9300 |
N1—N2 | 1.359 (2) | C19—C20 | 1.373 (3) |
N1—C10 | 1.362 (2) | C19—H19A | 0.9300 |
N1—C9 | 1.450 (2) | C5—C4 | 1.375 (3) |
O1—C7 | 1.213 (2) | C5—H5A | 0.9300 |
C17—C22 | 1.384 (3) | C11—C12 | 1.399 (3) |
C17—C18 | 1.385 (3) | C2—C3 | 1.366 (3) |
C17—C16 | 1.482 (3) | C2—H2B | 0.9300 |
N3—N2 | 1.297 (2) | C21—C20 | 1.382 (3) |
N3—C11 | 1.375 (3) | C21—H21A | 0.9300 |
C6—C1 | 1.382 (3) | C20—H20A | 0.9300 |
C6—C5 | 1.391 (3) | C3—C4 | 1.373 (3) |
C6—C7 | 1.489 (3) | C3—H3B | 0.9300 |
C8—C9 | 1.525 (3) | C4—H4A | 0.9300 |
C8—C7 | 1.529 (3) | C14—C15 | 1.361 (3) |
C8—H8A | 0.9800 | C14—C13 | 1.400 (3) |
C9—H9A | 0.9700 | C14—H14A | 0.9300 |
C9—H9B | 0.9700 | C15—H15A | 0.9300 |
C1—C2 | 1.371 (3) | C12—C13 | 1.363 (3) |
C10—C11 | 1.386 (3) | C12—H12A | 0.9300 |
C10—C15 | 1.394 (3) | C13—H13A | 0.9300 |
C16—O2—C8 | 115.86 (15) | C19—C18—C17 | 120.1 (2) |
N2—N1—C10 | 109.85 (17) | C19—C18—H18A | 120.0 |
N2—N1—C9 | 119.67 (16) | C17—C18—H18A | 120.0 |
C10—N1—C9 | 130.29 (17) | C20—C19—C18 | 120.2 (2) |
C22—C17—C18 | 119.53 (19) | C20—C19—H19A | 119.9 |
C22—C17—C16 | 122.21 (18) | C18—C19—H19A | 119.9 |
C18—C17—C16 | 118.19 (19) | C4—C5—C6 | 121.7 (2) |
N2—N3—C11 | 108.13 (18) | C4—C5—H5A | 119.2 |
C1—C6—C5 | 115.72 (19) | C6—C5—H5A | 119.2 |
C1—C6—C7 | 126.45 (19) | N3—C11—C10 | 108.78 (19) |
C5—C6—C7 | 117.82 (19) | N3—C11—C12 | 130.8 (2) |
O2—C8—C9 | 105.53 (15) | C10—C11—C12 | 120.4 (2) |
O2—C8—C7 | 109.03 (15) | C3—C2—C1 | 118.5 (2) |
C9—C8—C7 | 110.79 (16) | C3—C2—H2B | 120.8 |
O2—C8—H8A | 110.5 | C1—C2—H2B | 120.8 |
C9—C8—H8A | 110.5 | C22—C21—C20 | 119.8 (2) |
C7—C8—H8A | 110.5 | C22—C21—H21A | 120.1 |
N3—N2—N1 | 109.04 (17) | C20—C21—H21A | 120.1 |
O3—C16—O2 | 122.66 (18) | C19—C20—C21 | 120.2 (2) |
O3—C16—C17 | 124.95 (19) | C19—C20—H20A | 119.9 |
O2—C16—C17 | 112.38 (18) | C21—C20—H20A | 119.9 |
O1—C7—C6 | 120.20 (19) | C2—C3—C4 | 120.4 (2) |
O1—C7—C8 | 118.75 (18) | C2—C3—H3B | 119.8 |
C6—C7—C8 | 121.03 (17) | C4—C3—H3B | 119.8 |
N1—C9—C8 | 112.24 (17) | C3—C4—C5 | 120.0 (2) |
N1—C9—H9A | 109.2 | C3—C4—H4A | 120.0 |
C8—C9—H9A | 109.2 | C5—C4—H4A | 120.0 |
N1—C9—H9B | 109.2 | C15—C14—C13 | 122.6 (2) |
C8—C9—H9B | 109.2 | C15—C14—H14A | 118.7 |
H9A—C9—H9B | 107.9 | C13—C14—H14A | 118.7 |
F1—C1—C2 | 116.7 (2) | C14—C15—C10 | 115.8 (2) |
F1—C1—C6 | 119.51 (18) | C14—C15—H15A | 122.1 |
C2—C1—C6 | 123.8 (2) | C10—C15—H15A | 122.1 |
N1—C10—C11 | 104.19 (17) | C13—C12—C11 | 117.2 (2) |
N1—C10—C15 | 133.3 (2) | C13—C12—H12A | 121.4 |
C11—C10—C15 | 122.5 (2) | C11—C12—H12A | 121.4 |
C21—C22—C17 | 120.2 (2) | C12—C13—C14 | 121.4 (2) |
C21—C22—H22A | 119.9 | C12—C13—H13A | 119.3 |
C17—C22—H22A | 119.9 | C14—C13—H13A | 119.3 |
C16—O2—C8—C9 | 168.65 (16) | C9—N1—C10—C15 | 6.6 (4) |
C16—O2—C8—C7 | −72.3 (2) | C18—C17—C22—C21 | 1.0 (3) |
C11—N3—N2—N1 | −0.5 (2) | C16—C17—C22—C21 | −175.9 (2) |
C10—N1—N2—N3 | 0.3 (2) | C22—C17—C18—C19 | 0.9 (3) |
C9—N1—N2—N3 | 175.79 (17) | C16—C17—C18—C19 | 177.9 (2) |
C8—O2—C16—O3 | −8.9 (3) | C17—C18—C19—C20 | −2.0 (3) |
C8—O2—C16—C17 | 169.57 (16) | C1—C6—C5—C4 | 1.0 (3) |
C22—C17—C16—O3 | 167.6 (2) | C7—C6—C5—C4 | 179.8 (2) |
C18—C17—C16—O3 | −9.3 (3) | N2—N3—C11—C10 | 0.6 (2) |
C22—C17—C16—O2 | −10.9 (3) | N2—N3—C11—C12 | −179.3 (2) |
C18—C17—C16—O2 | 172.22 (18) | N1—C10—C11—N3 | −0.4 (2) |
C1—C6—C7—O1 | 177.4 (2) | C15—C10—C11—N3 | 178.39 (19) |
C5—C6—C7—O1 | −1.3 (3) | N1—C10—C11—C12 | 179.50 (19) |
C1—C6—C7—C8 | −4.3 (3) | C15—C10—C11—C12 | −1.7 (3) |
C5—C6—C7—C8 | 177.00 (18) | F1—C1—C2—C3 | −179.4 (2) |
O2—C8—C7—O1 | −14.0 (3) | C6—C1—C2—C3 | −0.3 (4) |
C9—C8—C7—O1 | 101.7 (2) | C17—C22—C21—C20 | −1.7 (4) |
O2—C8—C7—C6 | 167.59 (17) | C18—C19—C20—C21 | 1.3 (4) |
C9—C8—C7—C6 | −76.7 (2) | C22—C21—C20—C19 | 0.6 (4) |
N2—N1—C9—C8 | −92.3 (2) | C1—C2—C3—C4 | 1.1 (4) |
C10—N1—C9—C8 | 82.1 (3) | C2—C3—C4—C5 | −0.8 (4) |
O2—C8—C9—N1 | −75.6 (2) | C6—C5—C4—C3 | −0.3 (4) |
C7—C8—C9—N1 | 166.56 (16) | C13—C14—C15—C10 | 0.4 (4) |
C5—C6—C1—F1 | 178.43 (18) | N1—C10—C15—C14 | 179.2 (2) |
C7—C6—C1—F1 | −0.3 (3) | C11—C10—C15—C14 | 0.9 (3) |
C5—C6—C1—C2 | −0.7 (3) | N3—C11—C12—C13 | −178.9 (2) |
C7—C6—C1—C2 | −179.5 (2) | C10—C11—C12—C13 | 1.2 (3) |
N2—N1—C10—C11 | 0.1 (2) | C11—C12—C13—C14 | 0.0 (4) |
C9—N1—C10—C11 | −174.82 (18) | C15—C14—C13—C12 | −0.9 (4) |
N2—N1—C10—C15 | −178.5 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
C3—H3B···O3i | 0.93 | 2.53 | 3.375 (3) | 152 |
C8—H8A···F1 | 0.98 | 2.27 | 2.753 (2) | 110 |
Symmetry code: (i) −x+1, −y, −z. |
Experimental details
Crystal data | |
Chemical formula | C22H16FN3O3 |
Mr | 389.38 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 294 |
a, b, c (Å) | 9.8372 (11), 9.8985 (12), 11.6126 (13) |
α, β, γ (°) | 115.187 (2), 101.572 (2), 103.929 (2) |
V (Å3) | 932.17 (19) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.10 |
Crystal size (mm) | 0.32 × 0.25 × 0.10 |
Data collection | |
Diffractometer | Siemens SMART 1000 CCD area-detector |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.968, 0.990 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 5309, 3612, 2543 |
Rint | 0.019 |
(sin θ/λ)max (Å−1) | 0.618 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.053, 0.118, 1.04 |
No. of reflections | 3612 |
No. of parameters | 262 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.14, −0.21 |
Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 1997a), SHELXL97 (Sheldrick, 1997a), SHELXTL (Sheldrick, 1997b), PARST (Nardelli, 1995) and PLATON (Spek, 2003).
D—H···A | D—H | H···A | D···A | D—H···A |
C3—H3B···O3i | 0.93 | 2.53 | 3.375 (3) | 152.03 |
C8—H8A···F1 | 0.98 | 2.27 | 2.753 (2) | 109.51 |
Symmetry code: (i) −x+1, −y, −z. |
We have recently reported the structure of 3-(1H-Benzotriazol-1-yl)-1 -(2-fluorobenzoyl)ethyl nicotinate, (II), (Wan et al., 2007). As part of our ongoing studies to search for benzotriazole derivatives with higher pharmacological activities, such as antifungal, antitumor and antineoplastic, the title compound (I) was synthesized and its crystal structure is reported here.
In the molecule of the title compound, (I), (Fig. 1) the bond lengths and angles are generally within normal ranges (Allen et al., 1987), and are comparable to those in the related compound (II). In (I), the benzotriazole group is essentially planar, with a dihedral angle of 0.99 (1)° between triazole A (N1—N3/C10/C11) and benzene B (C10—C15) rings. Rings C (C1—C6) and D (C17—C22) are oriented with respect to the benzotriazole system at dihedral angles of 3.22 (1) and 86.48 (1)°, respectively, while the dihedral angle between them is 88.08 (1)°. The intramolecular C—H···F hydrogen bond (Table 1) results in the formation of a six-membered ring E (F1/C1/C6—C8/H8A) (Fig. 1).
In the crystal structure, intermolecular C—H···O hydrogen bonds (Table 1), link the molecules into centrosymmetric dimers (Fig. 2). The packing is further stabilized by π-π interactions involving the C rings with centroid-centroid distance of 3.601 (2) Å (symmetry code: 1 - x, -y, -z).