2-(1H-Benzotriazol-1-yl)-1-(2-fluoro-benzo-yl)ethyl 4-methyl-benzoate.

In the crystal structure of the title compound, C(23)H(18)FN(3)O(3), inter-molecular C-H⋯N hydrogen bonds link the mol-ecules into chains extended along the c axis. The packing is further stabilized by weak C-H⋯O and C-H⋯F inter-actions. The F atom is disordered over two equally occupied 1- and 5-positions of the benzene ring.

Related literature

For the pharmacological activity of 1H-benzotriazole and its derivatives, see: Chen & Wu (2005 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C23H18FN3O3

M = 403.40

Monoclinic,

a = 20.478 (4) Å

b = 19.570 (4) Å

c = 9.969 (2) Å

β = 107.12 (3)°

V = 3818.0 (13) Å3

Z = 8

Mo Kα radiation

μ = 0.10 mm−1

T = 293 K

0.10 × 0.06 × 0.02 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 1997 ▶) T min = 0.990, T max = 0.998

19476 measured reflections

3368 independent reflections

2698 reflections with I > 2σ(I)

R int = 0.058

Refinement

R[F 2 > 2σ(F 2)] = 0.064

wR(F 2) = 0.177

S = 1.08

3368 reflections

282 parameters

2 restraints

H-atom parameters constrained

Δρmax = 0.38 e Å−3

Δρmin = −0.27 e Å−3

Data collection: SMART (Bruker, 1997 ▶); cell refinement: SAINT (Bruker, 1997 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809029481/at2823sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809029481/at2823Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C23H18FN3O3	F(000) = 1680
Mr = 403.40	Dx = 1.404 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 3992 reflections
a = 20.478 (4) Å	θ = 2.1–25.0°
b = 19.570 (4) Å	µ = 0.10 mm−1
c = 9.969 (2) Å	T = 293 K
β = 107.12 (3)°	Block, colourless
V = 3818.0 (13) Å3	0.10 × 0.06 × 0.02 mm
Z = 8

Bruker SMART CCD diffractometer	3368 independent reflections
Radiation source: fine-focus sealed tube	2698 reflections with I > 2σ(I)
graphite	Rint = 0.058
ω scans	θmax = 25.0°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 1997)	h = −24→24
Tmin = 0.990, Tmax = 0.998	k = −23→23
19476 measured reflections	l = −11→11

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)] = 0.064	H-atom parameters constrained
wR(F2) = 0.177	w = 1/[σ2(Fo2) + (0.0959P)2 + 1.3136P] where P = (Fo2 + 2Fc2)/3
S = 1.08	(Δ/σ)max = 0.031
3368 reflections	Δρmax = 0.38 e Å−3
282 parameters	Δρmin = −0.26 e Å−3
2 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0028 (6)

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	Occ. (<1)
F1	0.46661 (19)	0.21126 (19)	0.3054 (4)	0.0709 (10)	0.50
F1'	0.24580 (17)	0.2535 (2)	0.3171 (4)	0.0717 (12)	0.50
O1	0.29447 (10)	0.12509 (10)	0.30001 (18)	0.0462 (5)
O2	0.35449 (9)	0.05690 (8)	0.13268 (16)	0.0371 (5)
O3	0.43939 (11)	0.06667 (10)	0.3332 (2)	0.0622 (7)
N1	0.23322 (11)	0.12861 (10)	−0.02778 (19)	0.0326 (5)
N2	0.19010 (12)	0.17037 (10)	0.0132 (2)	0.0378 (5)
N3	0.13058 (12)	0.14092 (11)	−0.0135 (2)	0.0401 (6)
C1	0.41929 (16)	0.25100 (14)	0.3243 (3)	0.0452 (7)
H1A	0.4518	0.2210	0.3024	0.054*	0.50
C2	0.44099 (19)	0.31500 (17)	0.3776 (3)	0.0602 (9)
H2	0.4862	0.3286	0.3936	0.072*
C3	0.3935 (2)	0.35812 (16)	0.4063 (3)	0.0649 (10)
H3	0.4064	0.4018	0.4405	0.078*
C4	0.3281 (2)	0.33705 (15)	0.3850 (3)	0.0603 (9)
H4	0.2964	0.3662	0.4053	0.072*
C5	0.30868 (16)	0.27283 (14)	0.3337 (3)	0.0487 (8)
H5A	0.2624	0.2585	0.3204	0.058*	0.50
C6	0.35371 (14)	0.22830 (13)	0.3012 (2)	0.0367 (6)
C7	0.33146 (13)	0.15790 (13)	0.2505 (2)	0.0349 (6)
C8	0.35328 (14)	0.12962 (12)	0.1289 (2)	0.0358 (6)
H8	0.3989	0.1469	0.1339	0.043*
C9	0.30282 (13)	0.15017 (12)	−0.0110 (2)	0.0365 (6)
H9A	0.3036	0.1995	−0.0199	0.044*
H9B	0.3178	0.1307	−0.0864	0.044*
C10	0.20015 (13)	0.07007 (12)	−0.0843 (2)	0.0312 (6)
C11	0.21918 (14)	0.01290 (12)	−0.1472 (2)	0.0361 (6)
H11	0.2632	0.0075	−0.1538	0.043*
C12	0.16911 (14)	−0.03490 (13)	−0.1989 (3)	0.0397 (7)
H12	0.1795	−0.0740	−0.2417	0.048*
C13	0.10262 (14)	−0.02655 (14)	−0.1889 (3)	0.0435 (7)
H13	0.0701	−0.0600	−0.2261	0.052*
C14	0.08430 (14)	0.02928 (14)	−0.1262 (3)	0.0418 (7)
H14	0.0403	0.0342	−0.1187	0.050*
C15	0.13458 (13)	0.07866 (12)	−0.0740 (2)	0.0341 (6)
C16	0.40188 (14)	0.03020 (14)	0.2459 (3)	0.0439 (7)
C17	0.40226 (13)	−0.04463 (13)	0.2469 (2)	0.0382 (6)
C18	0.36063 (14)	−0.08304 (13)	0.1382 (3)	0.0391 (6)
H18	0.3305	−0.0613	0.0618	0.047*
C19	0.36382 (15)	−0.15284 (13)	0.1430 (3)	0.0397 (6)
H19	0.3358	−0.1781	0.0692	0.048*
C20	0.40830 (14)	−0.18695 (14)	0.2562 (3)	0.0418 (7)
C21	0.44946 (15)	−0.14802 (15)	0.3646 (3)	0.0448 (7)
H21	0.4795	−0.1697	0.4412	0.054*
C22	0.44658 (14)	−0.07813 (14)	0.3607 (3)	0.0449 (7)
H22	0.4745	−0.0529	0.4346	0.054*
C23	0.41090 (17)	−0.26339 (14)	0.2594 (3)	0.0553 (8)
H23A	0.4499	−0.2781	0.3338	0.083*
H23B	0.4145	−0.2801	0.1714	0.083*
H23C	0.3700	−0.2809	0.2751	0.083*

	U11	U22	U33	U12	U13	U23
F1	0.056 (2)	0.074 (2)	0.086 (3)	−0.018 (2)	0.027 (2)	−0.013 (2)
F1'	0.034 (2)	0.099 (3)	0.070 (2)	0.0195 (19)	−0.0037 (17)	−0.037 (2)
O1	0.0466 (12)	0.0547 (12)	0.0385 (10)	−0.0151 (9)	0.0143 (9)	−0.0042 (9)
O2	0.0374 (10)	0.0336 (9)	0.0341 (9)	0.0032 (8)	0.0012 (8)	−0.0012 (7)
O3	0.0624 (15)	0.0522 (12)	0.0512 (13)	0.0025 (11)	−0.0156 (11)	−0.0096 (10)
N1	0.0364 (12)	0.0303 (11)	0.0287 (11)	0.0038 (9)	0.0059 (9)	0.0007 (8)
N2	0.0453 (14)	0.0351 (11)	0.0301 (11)	0.0105 (10)	0.0065 (10)	−0.0004 (9)
N3	0.0426 (14)	0.0419 (13)	0.0333 (12)	0.0087 (10)	0.0069 (10)	−0.0014 (9)
C1	0.0571 (19)	0.0436 (16)	0.0391 (15)	−0.0061 (14)	0.0209 (14)	0.0011 (12)
C2	0.078 (2)	0.060 (2)	0.0430 (17)	−0.0303 (18)	0.0181 (16)	0.0019 (14)
C3	0.113 (3)	0.0395 (17)	0.0376 (17)	−0.0130 (19)	0.0156 (19)	0.0022 (13)
C4	0.089 (3)	0.0447 (17)	0.0426 (17)	0.0191 (18)	0.0129 (17)	−0.0022 (14)
C5	0.057 (2)	0.0470 (17)	0.0339 (14)	0.0092 (14)	0.0009 (13)	−0.0034 (12)
C6	0.0462 (17)	0.0371 (14)	0.0244 (12)	−0.0004 (12)	0.0069 (11)	0.0021 (10)
C7	0.0308 (14)	0.0422 (14)	0.0285 (12)	−0.0025 (11)	0.0039 (11)	0.0057 (11)
C8	0.0369 (15)	0.0328 (13)	0.0361 (14)	−0.0027 (11)	0.0082 (12)	−0.0007 (11)
C9	0.0429 (16)	0.0329 (13)	0.0321 (13)	−0.0008 (11)	0.0082 (12)	0.0018 (10)
C10	0.0348 (14)	0.0309 (13)	0.0245 (12)	0.0034 (10)	0.0034 (10)	0.0022 (10)
C11	0.0377 (15)	0.0378 (14)	0.0314 (13)	0.0071 (11)	0.0079 (11)	−0.0006 (11)
C12	0.0440 (17)	0.0340 (14)	0.0365 (14)	0.0032 (11)	0.0046 (12)	−0.0061 (11)
C13	0.0387 (16)	0.0416 (15)	0.0413 (15)	−0.0038 (12)	−0.0020 (12)	−0.0023 (12)
C14	0.0334 (15)	0.0512 (17)	0.0378 (14)	0.0042 (12)	0.0058 (12)	0.0023 (12)
C15	0.0370 (15)	0.0344 (13)	0.0268 (12)	0.0075 (11)	0.0029 (11)	0.0016 (10)
C16	0.0405 (16)	0.0475 (16)	0.0356 (15)	0.0056 (13)	−0.0012 (13)	−0.0016 (12)
C17	0.0388 (15)	0.0419 (15)	0.0310 (13)	0.0085 (12)	0.0058 (11)	−0.0004 (11)
C18	0.0425 (16)	0.0430 (15)	0.0285 (13)	0.0082 (12)	0.0055 (12)	0.0028 (11)
C19	0.0514 (17)	0.0407 (15)	0.0268 (13)	0.0093 (12)	0.0110 (12)	−0.0001 (11)
C20	0.0509 (18)	0.0456 (16)	0.0364 (14)	0.0138 (13)	0.0244 (13)	0.0071 (12)
C21	0.0438 (17)	0.0564 (18)	0.0339 (14)	0.0192 (14)	0.0109 (13)	0.0098 (13)
C22	0.0388 (16)	0.0559 (18)	0.0347 (14)	0.0100 (13)	0.0025 (12)	0.0005 (12)
C23	0.072 (2)	0.0493 (17)	0.0518 (17)	0.0197 (15)	0.0292 (16)	0.0130 (14)

F1—C1	1.298 (4)	C9—H9A	0.9700
F1—H1A	0.3515	C9—H9B	0.9700
F1'—C5	1.305 (4)	C10—C15	1.387 (3)
F1'—H5A	0.3449	C10—C11	1.393 (3)
O1—C7	1.204 (3)	C11—C12	1.371 (4)
O2—C16	1.358 (3)	C11—H11	0.9300
O2—C8	1.424 (3)	C12—C13	1.403 (4)
O3—C16	1.209 (3)	C12—H12	0.9300
N1—N2	1.352 (3)	C13—C14	1.365 (4)
N1—C10	1.365 (3)	C13—H13	0.9300
N1—C9	1.448 (3)	C14—C15	1.396 (4)
N2—N3	1.303 (3)	C14—H14	0.9300
N3—C15	1.373 (3)	C16—C17	1.465 (4)
C1—C6	1.368 (4)	C17—C18	1.387 (4)
C1—C2	1.382 (4)	C17—C22	1.390 (4)
C1—H1A	0.9599	C18—C19	1.368 (3)
C2—C3	1.379 (5)	C18—H18	0.9300
C2—H2	0.9300	C19—C20	1.394 (4)
C3—C4	1.357 (5)	C19—H19	0.9300
C3—H3	0.9300	C20—C21	1.386 (4)
C4—C5	1.371 (4)	C20—C23	1.497 (4)
C4—H4	0.9300	C21—C22	1.369 (4)
C5—C6	1.375 (4)	C21—H21	0.9300
C5—H5A	0.9601	C22—H22	0.9300
C6—C7	1.492 (4)	C23—H23A	0.9600
C7—C8	1.515 (3)	C23—H23B	0.9600
C8—C9	1.525 (3)	C23—H23C	0.9600
C8—H8	0.9800
C1—F1—H1A	13.4	H9A—C9—H9B	107.6
C5—F1'—H5A	1.9	N1—C10—C15	104.0 (2)
C16—O2—C8	114.16 (19)	N1—C10—C11	133.5 (2)
N2—N1—C10	110.1 (2)	C15—C10—C11	122.4 (2)
N2—N1—C9	119.8 (2)	C12—C11—C10	116.1 (2)
C10—N1—C9	130.1 (2)	C12—C11—H11	122.0
N3—N2—N1	109.03 (19)	C10—C11—H11	122.0
N2—N3—C15	108.0 (2)	C11—C12—C13	121.9 (2)
F1—C1—C6	121.2 (3)	C11—C12—H12	119.1
F1—C1—C2	115.4 (3)	C13—C12—H12	119.1
C6—C1—C2	123.2 (3)	C14—C13—C12	121.9 (3)
F1—C1—H1A	4.9	C14—C13—H13	119.0
C6—C1—H1A	118.4	C12—C13—H13	119.0
C2—C1—H1A	118.4	C13—C14—C15	116.9 (3)
C3—C2—C1	117.9 (3)	C13—C14—H14	121.5
C3—C2—H2	121.1	C15—C14—H14	121.5
C1—C2—H2	121.1	N3—C15—C10	108.9 (2)
C4—C3—C2	120.3 (3)	N3—C15—C14	130.2 (2)
C4—C3—H3	119.8	C10—C15—C14	120.8 (2)
C2—C3—H3	119.8	O3—C16—O2	121.2 (2)
C3—C4—C5	120.1 (3)	O3—C16—C17	125.7 (2)
C3—C4—H4	119.9	O2—C16—C17	113.1 (2)
C5—C4—H4	119.9	C18—C17—C22	119.0 (2)
F1'—C5—C4	118.7 (3)	C18—C17—C16	122.4 (2)
F1'—C5—C6	119.5 (3)	C22—C17—C16	118.6 (2)
C4—C5—C6	121.8 (3)	C19—C18—C17	120.1 (2)
F1'—C5—H5A	0.7	C19—C18—H18	119.9
C4—C5—H5A	119.1	C17—C18—H18	119.9
C6—C5—H5A	119.1	C18—C19—C20	121.3 (2)
C1—C6—C5	116.6 (3)	C18—C19—H19	119.3
C1—C6—C7	122.9 (2)	C20—C19—H19	119.4
C5—C6—C7	120.4 (3)	C21—C20—C19	118.0 (2)
O1—C7—C6	121.3 (2)	C21—C20—C23	121.5 (3)
O1—C7—C8	120.2 (2)	C19—C20—C23	120.4 (3)
C6—C7—C8	118.4 (2)	C22—C21—C20	121.0 (2)
O2—C8—C7	110.6 (2)	C22—C21—H21	119.5
O2—C8—C9	106.83 (19)	C20—C21—H21	119.5
C7—C8—C9	110.8 (2)	C21—C22—C17	120.4 (3)
O2—C8—H8	109.5	C21—C22—H22	119.8
C7—C8—H8	109.5	C17—C22—H22	119.8
C9—C8—H8	109.5	C20—C23—H23A	109.5
N1—C9—C8	114.0 (2)	C20—C23—H23B	109.5
N1—C9—H9A	108.7	H23A—C23—H23B	109.5
C8—C9—H9A	108.7	C20—C23—H23C	109.5
N1—C9—H9B	108.7	H23A—C23—H23C	109.5
C8—C9—H9B	108.7	H23B—C23—H23C	109.5
C10—N1—N2—N3	0.5 (2)	C9—N1—C10—C15	−178.9 (2)
C9—N1—N2—N3	179.16 (19)	N2—N1—C10—C11	176.5 (2)
N1—N2—N3—C15	−0.3 (2)	C9—N1—C10—C11	−2.0 (4)
F1—C1—C2—C3	−176.8 (3)	N1—C10—C11—C12	−176.5 (2)
C6—C1—C2—C3	−1.2 (4)	C15—C10—C11—C12	−0.1 (3)
C1—C2—C3—C4	1.3 (4)	C10—C11—C12—C13	0.1 (4)
C2—C3—C4—C5	−0.5 (4)	C11—C12—C13—C14	−0.6 (4)
C3—C4—C5—F1'	178.6 (3)	C12—C13—C14—C15	1.0 (4)
C3—C4—C5—C6	−0.6 (4)	N2—N3—C15—C10	0.0 (3)
F1—C1—C6—C5	175.6 (3)	N2—N3—C15—C14	−177.3 (2)
C2—C1—C6—C5	0.1 (4)	N1—C10—C15—N3	0.2 (2)
F1—C1—C6—C7	−1.4 (4)	C11—C10—C15—N3	−177.1 (2)
C2—C1—C6—C7	−176.8 (2)	N1—C10—C15—C14	177.9 (2)
F1'—C5—C6—C1	−178.4 (3)	C11—C10—C15—C14	0.5 (4)
C4—C5—C6—C1	0.8 (4)	C13—C14—C15—N3	176.1 (2)
F1'—C5—C6—C7	−1.4 (4)	C13—C14—C15—C10	−1.0 (4)
C4—C5—C6—C7	177.8 (2)	C8—O2—C16—O3	−0.7 (4)
C1—C6—C7—O1	137.2 (3)	C8—O2—C16—C17	−179.7 (2)
C5—C6—C7—O1	−39.6 (4)	O3—C16—C17—C18	−175.6 (3)
C1—C6—C7—C8	−46.1 (3)	O2—C16—C17—C18	3.4 (4)
C5—C6—C7—C8	137.1 (2)	O3—C16—C17—C22	3.7 (4)
C16—O2—C8—C7	−65.0 (3)	O2—C16—C17—C22	−177.3 (2)
C16—O2—C8—C9	174.4 (2)	C22—C17—C18—C19	−0.5 (4)
O1—C7—C8—O2	−28.4 (3)	C16—C17—C18—C19	178.8 (2)
C6—C7—C8—O2	154.9 (2)	C17—C18—C19—C20	0.2 (4)
O1—C7—C8—C9	89.9 (3)	C18—C19—C20—C21	0.0 (4)
C6—C7—C8—C9	−86.8 (3)	C18—C19—C20—C23	179.9 (3)
N2—N1—C9—C8	90.5 (3)	C19—C20—C21—C22	0.0 (4)
C10—N1—C9—C8	−91.1 (3)	C23—C20—C21—C22	−179.9 (3)
O2—C8—C9—N1	63.0 (3)	C20—C21—C22—C17	−0.3 (4)
C7—C8—C9—N1	−57.5 (3)	C18—C17—C22—C21	0.5 (4)
N2—N1—C10—C15	−0.4 (2)	C16—C17—C22—C21	−178.8 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8···F1	0.98	2.24	2.938 (5)	127
C9—H9A···N2i	0.97	2.55	3.515 (3)	174
C12—H12···O1ii	0.93	2.48	3.118 (4)	126
C18—H18···O2	0.93	2.43	2.741 (3)	100
C22—H22···O3iii	0.93	2.48	3.259 (4)	142
C23—H23C···F1'iv	0.96	2.37	3.090 (5)	131

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8⋯F1	0.98	2.24	2.938 (5)	127
C9—H9A⋯N2i	0.97	2.55	3.515 (3)	174
C12—H12⋯O1ii	0.93	2.48	3.118 (4)	126
C22—H22⋯O3iii	0.93	2.48	3.259 (4)	142
C23—H23C⋯F1′iv	0.96	2.37	3.090 (5)	131

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .