2-(1H-Benzotriazol-1-yl)-1-(2-fluoro­benzo­yl)ethyl isonicotinate

Wan, J.; Li, F.; Zeng, W.-L.; Li, J.; Bi, S.

doi:10.1107/S1600536807043310

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2-(1H-Benzotriazol-1-yl)-1-(2-fluorobenzoyl)ethyl isonicotinate

J. Wan, F. Li, W.-L. Zeng, J. Li and S. Bi

The title compound, C₂₁H₁₅FN₄O₃, has a nonplanar conformation. The mean plane of the benzotriazole group makes dihedral angles of 79.30 (1) and 11.64 (1)° with the pyridine and benzene rings, respectively. An intramolecular C—H

F hydrogen bond forms a six-membered ring. Molecules are linked into dimers by C—H

O hydrogen bonds, and are linked into chains along the b axis by intermolecular C—H

N hydrogen bonds. The packing is further stabilized by weak π–π interactions with a distance of 3.752 (2) Å between the centroids of the benzene rings.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807043310/at2386sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807043310/at2386Isup2.hkl Contains datablock I

CCDC reference: 636551

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.003 Å
R factor = 0.042
wR factor = 0.112
Data-to-parameter ratio = 13.5

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.97
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT153_ALERT_1_C The su's on the Cell Axes   are Equal (x 100000)        400 Ang.
PLAT154_ALERT_1_C The su's on the Cell Angles are Equal  (x 10000)        500 Deg.

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
PLAT793_ALERT_1_G Check the Absolute Configuration of C8     = ...          R

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   4 ALERT level C = Check and explain
   3 ALERT level G = General alerts; check

   6 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
   1 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

Comment top

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···Cg3^iv = 3.752 Å [symmetry code: (iv) -x, 1 - y, 1 - z, Cg3 is the centroid of the C1—C6 benzene ring].

Related literature top

For a related compound, see: Han et al. (2007). For related literature, see: Allen et al. (1987).

Experimental top

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.

Structure description top

For a related compound, see: Han et al. (2007). For related literature, see: Allen et al. (1987).

Computing details top

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).

Figures top

	Fig. 1. The structure of the compound (I) showing 50% probability displacement ellipsoids and the atom numbering scheme.
	Fig. 2. A packing diagram of (I), viewed down the c axis. Hydrogen bonds are indicated by dashed lines.

2-(1H-Benzotriazol-1-yl)-1-(2-fluorobenzoyl)ethyl isonicotinate top

Crystal data top

C₂₁H₁₅FN₄O₃	Z = 2
M_r = 390.37	F(000) = 404
Triclinic, P1	D_x = 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

Data collection top

Siemens SMART 1000 CCD area-detector diffractometer	3544 independent reflections
Radiation source: fine-focus sealed tube	2651 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.015
Detector resolution: 8.33 pixels mm^-1	θ_max = 26.0°, θ_min = 2.1°
ω scans	h = −8→11
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −11→12
T_min = 0.974, T_max = 0.996	l = −13→9
5185 measured reflections

Refinement top

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(F_o²) + (0.0489P)² + 0.134P] where P = (F_o² + 2F_c²)/3
3544 reflections	(Δ/σ)_max < 0.001
262 parameters	Δρ_max = 0.14 e Å⁻³
0 restraints	Δρ_min = −0.18 e Å⁻³

Crystal data top

C₂₁H₁₅FN₄O₃	γ = 103.444 (5)°
M_r = 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)°

Data collection top

Siemens SMART 1000 CCD area-detector diffractometer	3544 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2651 reflections with I > 2σ(I)
T_min = 0.974, T_max = 0.996	R_int = 0.015
5185 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	0 restraints
wR(F²) = 0.112	H-atom parameters constrained
S = 1.04	Δρ_max = 0.14 e Å⁻³
3544 reflections	Δρ_min = −0.18 e Å⁻³
262 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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
M_r	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)
T_min, T_max	0.974, 0.996
No. of measured, independent and observed [I > 2σ(I)] reflections	5185, 3544, 2651
R_int	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
Δρ_max, Δρ_min (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).

Hydrogen-bond geometry (Å, º) top

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.

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