Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807043310/at2386sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807043310/at2386Isup2.hkl |
CCDC reference: 636551
The title compound (I) was prepared according to the literature method of Han et al. (2007). Single crystals of (I) suitable for X-ray diffraction were obtained by slow evaporation of an ethyl acetate solution at room temperature over a period of 6 days.
All H atoms were located in difference Fourier maps and constrained to ride on their parent atoms, with C—H distances in the range 0.93–0.98 Å, and with Uiso(H) = 1.2 Ueq(C) H atoms.
We have recently reported the structure of 2-(1H-benzotriazol-1-yl)-1-(4-chlorobenzoyl)ethyl isonicotinate (II) (Han et al., 2007). As part of our ongoing studies of triazole derivatives, the title compound, (I), was synthesized and its structure is reported here.
All the bond lengths and angles are within normal ranges (Allen et al., 1987) and are comparable to those in the related compound (II). In (I), the benzotriazole system is essentially planar, with a dihedral angle of 1.89 (1)° between triazole ring A(N1—N3/C10/C11) and benzene ring B(C10—C15). The mean plane of the benzotriazole group makes dihedral angles 79.30 (1)° and 11.64 (1)° with the C(N4/C17—C21) and D(C1—C6) rings, respectively. The dihedral angle between the planes of the latter two aromatic rings is 76.08 (1)°. There is an intramolecular C8—H8A···F1 hydrogen bond, forming a six-membered ring.
In the crystal structure, molecules of (I) are linked into dimers by C15—H15A···O1ii hydrogen bonds [symmetry code: (ii) 1 - x, 2 - y, 2 - z], and are linked into chains along the b axis by intermolecular C2—H2B···N3i and C21—H21A···N2iii [symmetry codes: (i) 1 - x, 1 - y, 1 - z; (iii) 1 - x, 1 - y, 2 - z] hydrogen bonds (Table 1 and Fig. 2). The packing is further stabilized by weak π-π interactions involving the C1—C6 benzene rings: Cg3···Cg3iv = 3.752 Å [symmetry code: (iv) -x, 1 - y, 1 - z, Cg3 is the centroid of the C1—C6 benzene ring].
For a related compound, see: Han et al. (2007). For related literature, 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).
C21H15FN4O3 | Z = 2 |
Mr = 390.37 | F(000) = 404 |
Triclinic, P1 | Dx = 1.398 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 9.743 (4) Å | Cell parameters from 1764 reflections |
b = 10.226 (4) Å | θ = 2.4–25.1° |
c = 10.975 (4) Å | µ = 0.10 mm−1 |
α = 99.167 (5)° | T = 293 K |
β = 114.399 (5)° | Plate, yellow |
γ = 103.444 (5)° | 0.26 × 0.20 × 0.04 mm |
V = 927.4 (6) Å3 |
Siemens SMART 1000 CCD area-detector diffractometer | 3544 independent reflections |
Radiation source: fine-focus sealed tube | 2651 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.015 |
Detector resolution: 8.33 pixels mm-1 | θmax = 26.0°, θmin = 2.1° |
ω scans | h = −8→11 |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | k = −11→12 |
Tmin = 0.974, Tmax = 0.996 | l = −13→9 |
5185 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)] = 0.042 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.112 | H-atom parameters constrained |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0489P)2 + 0.134P] where P = (Fo2 + 2Fc2)/3 |
3544 reflections | (Δ/σ)max < 0.001 |
262 parameters | Δρmax = 0.14 e Å−3 |
0 restraints | Δρmin = −0.18 e Å−3 |
C21H15FN4O3 | γ = 103.444 (5)° |
Mr = 390.37 | V = 927.4 (6) Å3 |
Triclinic, P1 | Z = 2 |
a = 9.743 (4) Å | Mo Kα radiation |
b = 10.226 (4) Å | µ = 0.10 mm−1 |
c = 10.975 (4) Å | T = 293 K |
α = 99.167 (5)° | 0.26 × 0.20 × 0.04 mm |
β = 114.399 (5)° |
Siemens SMART 1000 CCD area-detector diffractometer | 3544 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 2651 reflections with I > 2σ(I) |
Tmin = 0.974, Tmax = 0.996 | Rint = 0.015 |
5185 measured reflections |
R[F2 > 2σ(F2)] = 0.042 | 0 restraints |
wR(F2) = 0.112 | H-atom parameters constrained |
S = 1.04 | Δρmax = 0.14 e Å−3 |
3544 reflections | Δρmin = −0.18 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 | 0.32317 (13) | 0.57552 (11) | 0.57280 (10) | 0.0669 (3) | |
O2 | 0.53117 (13) | 0.76959 (12) | 0.99687 (11) | 0.0488 (3) | |
O1 | 0.28064 (16) | 0.84106 (14) | 0.87200 (12) | 0.0671 (4) | |
N1 | 0.72690 (16) | 0.78363 (14) | 0.85732 (14) | 0.0471 (3) | |
C6 | 0.19491 (18) | 0.72253 (16) | 0.63796 (16) | 0.0439 (4) | |
O3 | 0.35710 (17) | 0.56942 (14) | 0.97541 (13) | 0.0697 (4) | |
C17 | 0.51604 (19) | 0.73892 (17) | 1.19893 (16) | 0.0451 (4) | |
C16 | 0.45878 (19) | 0.68059 (18) | 1.04674 (17) | 0.0464 (4) | |
C1 | 0.2037 (2) | 0.63174 (17) | 0.53563 (17) | 0.0484 (4) | |
N2 | 0.72997 (18) | 0.68140 (16) | 0.76401 (15) | 0.0615 (4) | |
C7 | 0.30749 (19) | 0.76998 (17) | 0.79067 (17) | 0.0451 (4) | |
C10 | 0.86206 (19) | 0.82372 (17) | 0.98201 (17) | 0.0460 (4) | |
C8 | 0.46330 (19) | 0.73576 (17) | 0.84731 (15) | 0.0441 (4) | |
H8A | 0.4426 | 0.6362 | 0.8070 | 0.053* | |
C9 | 0.58719 (19) | 0.82737 (18) | 0.81896 (17) | 0.0483 (4) | |
H9A | 0.5405 | 0.8219 | 0.7205 | 0.058* | |
H9B | 0.6188 | 0.9243 | 0.8718 | 0.058* | |
C11 | 0.9478 (2) | 0.73988 (19) | 0.95988 (19) | 0.0538 (4) | |
C2 | 0.0959 (2) | 0.5924 (2) | 0.39624 (18) | 0.0606 (5) | |
H2B | 0.1062 | 0.5311 | 0.3308 | 0.073* | |
N3 | 0.8622 (2) | 0.65436 (18) | 0.82430 (18) | 0.0692 (5) | |
N4 | 0.5995 (2) | 0.8432 (2) | 1.48007 (17) | 0.0724 (5) | |
C18 | 0.5974 (2) | 0.87952 (19) | 1.26949 (18) | 0.0555 (5) | |
H18A | 0.6272 | 0.9419 | 1.2247 | 0.067* | |
C5 | 0.0653 (2) | 0.7722 (2) | 0.59237 (19) | 0.0598 (5) | |
H5A | 0.0527 | 0.8316 | 0.6575 | 0.072* | |
C20 | 0.5256 (3) | 0.7073 (2) | 1.4117 (2) | 0.0700 (6) | |
H20A | 0.5036 | 0.6464 | 1.4609 | 0.084* | |
C21 | 0.4795 (2) | 0.6509 (2) | 1.2722 (2) | 0.0596 (5) | |
H21A | 0.4249 | 0.5554 | 1.2285 | 0.072* | |
C3 | −0.0276 (2) | 0.6459 (2) | 0.3560 (2) | 0.0694 (6) | |
H3B | −0.1011 | 0.6217 | 0.2619 | 0.083* | |
C19 | 0.6335 (3) | 0.9256 (2) | 1.4075 (2) | 0.0688 (5) | |
H19A | 0.6852 | 1.0212 | 1.4530 | 0.083* | |
C15 | 0.9200 (2) | 0.9256 (2) | 1.10816 (18) | 0.0572 (5) | |
H15A | 0.8621 | 0.9817 | 1.1222 | 0.069* | |
C14 | 1.0666 (2) | 0.9379 (2) | 1.2097 (2) | 0.0681 (5) | |
H14A | 1.1105 | 1.0055 | 1.2951 | 0.082* | |
C12 | 1.0973 (2) | 0.7530 (2) | 1.0670 (2) | 0.0700 (6) | |
H12A | 1.1552 | 0.6963 | 1.0544 | 0.084* | |
C4 | −0.0434 (2) | 0.7351 (2) | 0.4537 (2) | 0.0730 (6) | |
H4B | −0.1279 | 0.7702 | 0.4256 | 0.088* | |
C13 | 1.1537 (2) | 0.8527 (3) | 1.1903 (2) | 0.0722 (6) | |
H13A | 1.2527 | 0.8644 | 1.2635 | 0.087* |
U11 | U22 | U33 | U12 | U13 | U23 | |
F1 | 0.0665 (7) | 0.0814 (8) | 0.0574 (6) | 0.0381 (6) | 0.0304 (6) | 0.0078 (6) |
O2 | 0.0450 (6) | 0.0557 (7) | 0.0394 (6) | 0.0108 (5) | 0.0174 (5) | 0.0130 (5) |
O1 | 0.0720 (9) | 0.0846 (9) | 0.0491 (7) | 0.0428 (8) | 0.0279 (7) | 0.0073 (7) |
N1 | 0.0438 (8) | 0.0528 (8) | 0.0434 (7) | 0.0151 (6) | 0.0222 (6) | 0.0072 (6) |
C6 | 0.0414 (9) | 0.0447 (9) | 0.0425 (9) | 0.0117 (7) | 0.0193 (7) | 0.0095 (7) |
O3 | 0.0738 (9) | 0.0597 (8) | 0.0571 (8) | −0.0010 (7) | 0.0295 (7) | 0.0072 (7) |
C17 | 0.0388 (8) | 0.0551 (10) | 0.0441 (9) | 0.0198 (8) | 0.0184 (7) | 0.0178 (8) |
C16 | 0.0409 (9) | 0.0503 (10) | 0.0478 (9) | 0.0157 (8) | 0.0200 (8) | 0.0154 (8) |
C1 | 0.0448 (9) | 0.0510 (10) | 0.0501 (10) | 0.0157 (8) | 0.0242 (8) | 0.0109 (8) |
N2 | 0.0558 (10) | 0.0667 (10) | 0.0553 (9) | 0.0160 (8) | 0.0290 (8) | −0.0015 (8) |
C7 | 0.0470 (9) | 0.0448 (9) | 0.0445 (9) | 0.0155 (7) | 0.0234 (8) | 0.0091 (7) |
C10 | 0.0413 (9) | 0.0528 (10) | 0.0458 (9) | 0.0148 (8) | 0.0229 (8) | 0.0134 (8) |
C8 | 0.0451 (9) | 0.0486 (9) | 0.0357 (8) | 0.0167 (7) | 0.0171 (7) | 0.0079 (7) |
C9 | 0.0466 (9) | 0.0534 (10) | 0.0446 (9) | 0.0173 (8) | 0.0205 (8) | 0.0147 (8) |
C11 | 0.0487 (10) | 0.0600 (11) | 0.0598 (11) | 0.0201 (9) | 0.0321 (9) | 0.0135 (9) |
C2 | 0.0621 (12) | 0.0641 (12) | 0.0444 (10) | 0.0116 (10) | 0.0239 (9) | 0.0032 (9) |
N3 | 0.0610 (10) | 0.0742 (11) | 0.0722 (11) | 0.0265 (9) | 0.0363 (9) | 0.0007 (9) |
N4 | 0.0835 (12) | 0.0832 (13) | 0.0519 (9) | 0.0279 (10) | 0.0319 (9) | 0.0221 (9) |
C18 | 0.0616 (11) | 0.0549 (11) | 0.0467 (10) | 0.0169 (9) | 0.0225 (9) | 0.0179 (8) |
C5 | 0.0534 (11) | 0.0624 (11) | 0.0549 (11) | 0.0246 (9) | 0.0185 (9) | 0.0058 (9) |
C20 | 0.0790 (14) | 0.0865 (15) | 0.0598 (12) | 0.0287 (12) | 0.0406 (11) | 0.0357 (12) |
C21 | 0.0626 (12) | 0.0595 (11) | 0.0622 (12) | 0.0169 (9) | 0.0337 (10) | 0.0234 (9) |
C3 | 0.0577 (12) | 0.0771 (14) | 0.0476 (11) | 0.0116 (11) | 0.0092 (9) | 0.0117 (10) |
C19 | 0.0807 (14) | 0.0629 (12) | 0.0501 (11) | 0.0169 (11) | 0.0245 (10) | 0.0115 (10) |
C15 | 0.0551 (11) | 0.0655 (11) | 0.0477 (10) | 0.0227 (9) | 0.0229 (9) | 0.0076 (9) |
C14 | 0.0570 (12) | 0.0857 (15) | 0.0489 (11) | 0.0207 (11) | 0.0185 (10) | 0.0094 (10) |
C12 | 0.0528 (12) | 0.0891 (15) | 0.0828 (15) | 0.0365 (11) | 0.0369 (11) | 0.0288 (13) |
C4 | 0.0540 (12) | 0.0809 (14) | 0.0653 (13) | 0.0293 (11) | 0.0103 (10) | 0.0124 (11) |
C13 | 0.0483 (11) | 0.1031 (17) | 0.0608 (13) | 0.0257 (11) | 0.0197 (10) | 0.0277 (12) |
F1—C1 | 1.3583 (19) | C11—C12 | 1.402 (3) |
O2—C16 | 1.343 (2) | C2—C3 | 1.373 (3) |
O2—C8 | 1.4378 (19) | C2—H2B | 0.9300 |
O1—C7 | 1.2116 (19) | N4—C19 | 1.325 (3) |
N1—N2 | 1.3569 (19) | N4—C20 | 1.330 (3) |
N1—C10 | 1.362 (2) | C18—C19 | 1.377 (3) |
N1—C9 | 1.449 (2) | C18—H18A | 0.9300 |
C6—C1 | 1.384 (2) | C5—C4 | 1.371 (3) |
C6—C5 | 1.400 (2) | C5—H5A | 0.9300 |
C6—C7 | 1.491 (2) | C20—C21 | 1.382 (3) |
O3—C16 | 1.199 (2) | C20—H20A | 0.9300 |
C17—C21 | 1.379 (2) | C21—H21A | 0.9300 |
C17—C18 | 1.380 (2) | C3—C4 | 1.377 (3) |
C17—C16 | 1.488 (2) | C3—H3B | 0.9300 |
C1—C2 | 1.373 (2) | C19—H19A | 0.9300 |
N2—N3 | 1.302 (2) | C15—C14 | 1.362 (3) |
C7—C8 | 1.533 (2) | C15—H15A | 0.9300 |
C10—C11 | 1.388 (2) | C14—C13 | 1.400 (3) |
C10—C15 | 1.393 (2) | C14—H14A | 0.9300 |
C8—C9 | 1.519 (2) | C12—C13 | 1.364 (3) |
C8—H8A | 0.9800 | C12—H12A | 0.9300 |
C9—H9A | 0.9700 | C4—H4B | 0.9300 |
C9—H9B | 0.9700 | C13—H13A | 0.9300 |
C11—N3 | 1.377 (2) | ||
C16—O2—C8 | 116.12 (13) | C1—C2—C3 | 118.30 (18) |
N2—N1—C10 | 110.20 (14) | C1—C2—H2B | 120.9 |
N2—N1—C9 | 119.86 (14) | C3—C2—H2B | 120.9 |
C10—N1—C9 | 129.81 (14) | N2—N3—C11 | 108.27 (14) |
C1—C6—C5 | 116.08 (15) | C19—N4—C20 | 116.08 (17) |
C1—C6—C7 | 126.52 (15) | C19—C18—C17 | 118.69 (17) |
C5—C6—C7 | 117.39 (15) | C19—C18—H18A | 120.7 |
C21—C17—C18 | 117.94 (16) | C17—C18—H18A | 120.7 |
C21—C17—C16 | 119.07 (16) | C4—C5—C6 | 121.40 (18) |
C18—C17—C16 | 122.90 (15) | C4—C5—H5A | 119.3 |
O3—C16—O2 | 123.54 (16) | C6—C5—H5A | 119.3 |
O3—C16—C17 | 124.57 (16) | N4—C20—C21 | 124.06 (18) |
O2—C16—C17 | 111.86 (14) | N4—C20—H20A | 118.0 |
F1—C1—C2 | 117.06 (15) | C21—C20—H20A | 118.0 |
F1—C1—C6 | 119.34 (15) | C17—C21—C20 | 118.72 (19) |
C2—C1—C6 | 123.60 (17) | C17—C21—H21A | 120.6 |
N3—N2—N1 | 108.73 (14) | C20—C21—H21A | 120.6 |
O1—C7—C6 | 120.61 (15) | C2—C3—C4 | 120.54 (18) |
O1—C7—C8 | 118.60 (15) | C2—C3—H3B | 119.7 |
C6—C7—C8 | 120.73 (14) | C4—C3—H3B | 119.7 |
N1—C10—C11 | 104.13 (15) | N4—C19—C18 | 124.45 (19) |
N1—C10—C15 | 133.31 (16) | N4—C19—H19A | 117.8 |
C11—C10—C15 | 122.52 (16) | C18—C19—H19A | 117.8 |
O2—C8—C9 | 105.69 (13) | C14—C15—C10 | 115.87 (17) |
O2—C8—C7 | 108.33 (12) | C14—C15—H15A | 122.1 |
C9—C8—C7 | 111.49 (13) | C10—C15—H15A | 122.1 |
O2—C8—H8A | 110.4 | C15—C14—C13 | 122.52 (19) |
C9—C8—H8A | 110.4 | C15—C14—H14A | 118.7 |
C7—C8—H8A | 110.4 | C13—C14—H14A | 118.7 |
N1—C9—C8 | 111.36 (13) | C13—C12—C11 | 116.90 (18) |
N1—C9—H9A | 109.4 | C13—C12—H12A | 121.6 |
C8—C9—H9A | 109.4 | C11—C12—H12A | 121.6 |
N1—C9—H9B | 109.4 | C5—C4—C3 | 120.06 (19) |
C8—C9—H9B | 109.4 | C5—C4—H4B | 120.0 |
H9A—C9—H9B | 108.0 | C3—C4—H4B | 120.0 |
N3—C11—C10 | 108.67 (16) | C12—C13—C14 | 121.70 (19) |
N3—C11—C12 | 130.83 (17) | C12—C13—H13A | 119.2 |
C10—C11—C12 | 120.49 (18) | C14—C13—H13A | 119.2 |
C8—O2—C16—O3 | 9.6 (2) | N1—C10—C11—N3 | 0.32 (19) |
C8—O2—C16—C17 | −168.46 (12) | C15—C10—C11—N3 | −177.61 (16) |
C21—C17—C16—O3 | 15.3 (3) | N1—C10—C11—C12 | 179.33 (16) |
C18—C17—C16—O3 | −161.11 (18) | C15—C10—C11—C12 | 1.4 (3) |
C21—C17—C16—O2 | −166.66 (14) | F1—C1—C2—C3 | 178.98 (16) |
C18—C17—C16—O2 | 16.9 (2) | C6—C1—C2—C3 | −0.1 (3) |
C5—C6—C1—F1 | −177.74 (15) | N1—N2—N3—C11 | 0.2 (2) |
C7—C6—C1—F1 | 1.1 (3) | C10—C11—N3—N2 | −0.3 (2) |
C5—C6—C1—C2 | 1.3 (3) | C12—C11—N3—N2 | −179.20 (19) |
C7—C6—C1—C2 | −179.83 (17) | C21—C17—C18—C19 | −2.0 (3) |
C10—N1—N2—N3 | 0.0 (2) | C16—C17—C18—C19 | 174.45 (17) |
C9—N1—N2—N3 | −176.20 (14) | C1—C6—C5—C4 | −1.6 (3) |
C1—C6—C7—O1 | −174.06 (17) | C7—C6—C5—C4 | 179.40 (18) |
C5—C6—C7—O1 | 4.8 (2) | C19—N4—C20—C21 | −2.2 (3) |
C1—C6—C7—C8 | 8.8 (3) | C18—C17—C21—C20 | 0.1 (3) |
C5—C6—C7—C8 | −172.32 (15) | C16—C17—C21—C20 | −176.54 (17) |
N2—N1—C10—C11 | −0.20 (18) | N4—C20—C21—C17 | 2.2 (3) |
C9—N1—C10—C11 | 175.51 (15) | C1—C2—C3—C4 | −0.9 (3) |
N2—N1—C10—C15 | 177.39 (18) | C20—N4—C19—C18 | 0.0 (3) |
C9—N1—C10—C15 | −6.9 (3) | C17—C18—C19—N4 | 2.1 (3) |
C16—O2—C8—C9 | −166.09 (13) | N1—C10—C15—C14 | −177.50 (18) |
C16—O2—C8—C7 | 74.31 (17) | C11—C10—C15—C14 | −0.3 (3) |
O1—C7—C8—O2 | 13.9 (2) | C10—C15—C14—C13 | −0.9 (3) |
C6—C7—C8—O2 | −168.92 (13) | N3—C11—C12—C13 | 177.4 (2) |
O1—C7—C8—C9 | −101.99 (18) | C10—C11—C12—C13 | −1.3 (3) |
C6—C7—C8—C9 | 75.19 (19) | C6—C5—C4—C3 | 0.7 (3) |
N2—N1—C9—C8 | 86.68 (18) | C2—C3—C4—C5 | 0.6 (3) |
C10—N1—C9—C8 | −88.7 (2) | C11—C12—C13—C14 | 0.2 (3) |
O2—C8—C9—N1 | 69.41 (16) | C15—C14—C13—C12 | 1.0 (3) |
C7—C8—C9—N1 | −173.09 (13) |
D—H···A | D—H | H···A | D···A | D—H···A |
C2—H2B···N3i | 0.93 | 2.50 | 3.427 (3) | 172 |
C8—H8A···F1 | 0.98 | 2.25 | 2.759 (2) | 112 |
C15—H15A···O1ii | 0.93 | 2.54 | 3.452 (3) | 168 |
C21—H21A···N2iii | 0.93 | 2.57 | 3.398 (3) | 148 |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+1, −y+2, −z+2; (iii) −x+1, −y+1, −z+2. |
Experimental details
Crystal data | |
Chemical formula | C21H15FN4O3 |
Mr | 390.37 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 293 |
a, b, c (Å) | 9.743 (4), 10.226 (4), 10.975 (4) |
α, β, γ (°) | 99.167 (5), 114.399 (5), 103.444 (5) |
V (Å3) | 927.4 (6) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.10 |
Crystal size (mm) | 0.26 × 0.20 × 0.04 |
Data collection | |
Diffractometer | Siemens SMART 1000 CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.974, 0.996 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 5185, 3544, 2651 |
Rint | 0.015 |
(sin θ/λ)max (Å−1) | 0.617 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.042, 0.112, 1.04 |
No. of reflections | 3544 |
No. of parameters | 262 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.14, −0.18 |
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 |
C2—H2B···N3i | 0.93 | 2.50 | 3.427 (3) | 172.39 |
C8—H8A···F1 | 0.98 | 2.25 | 2.759 (2) | 111.67 |
C15—H15A···O1ii | 0.93 | 2.54 | 3.452 (3) | 168.35 |
C21—H21A···N2iii | 0.93 | 2.57 | 3.398 (3) | 148.19 |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+1, −y+2, −z+2; (iii) −x+1, −y+1, −z+2. |
We have recently reported the structure of 2-(1H-benzotriazol-1-yl)-1-(4-chlorobenzoyl)ethyl isonicotinate (II) (Han et al., 2007). As part of our ongoing studies of triazole derivatives, the title compound, (I), was synthesized and its structure is reported here.
All the bond lengths and angles are within normal ranges (Allen et al., 1987) and are comparable to those in the related compound (II). In (I), the benzotriazole system is essentially planar, with a dihedral angle of 1.89 (1)° between triazole ring A(N1—N3/C10/C11) and benzene ring B(C10—C15). The mean plane of the benzotriazole group makes dihedral angles 79.30 (1)° and 11.64 (1)° with the C(N4/C17—C21) and D(C1—C6) rings, respectively. The dihedral angle between the planes of the latter two aromatic rings is 76.08 (1)°. There is an intramolecular C8—H8A···F1 hydrogen bond, forming a six-membered ring.
In the crystal structure, molecules of (I) are linked into dimers by C15—H15A···O1ii hydrogen bonds [symmetry code: (ii) 1 - x, 2 - y, 2 - z], and are linked into chains along the b axis by intermolecular C2—H2B···N3i and C21—H21A···N2iii [symmetry codes: (i) 1 - x, 1 - y, 1 - z; (iii) 1 - x, 1 - y, 2 - z] hydrogen bonds (Table 1 and Fig. 2). The packing is further stabilized by weak π-π interactions involving the C1—C6 benzene rings: Cg3···Cg3iv = 3.752 Å [symmetry code: (iv) -x, 1 - y, 1 - z, Cg3 is the centroid of the C1—C6 benzene ring].