3-(1H-Benzotriazol-1-yl)-1-(2-fluoro­benzo­yl)ethyl nicotinate

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

doi:10.1107/S1600536807041967

3-(1H-Benzotriazol-1-yl)-1-(2-fluorobenzoyl)ethyl nicotinate

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

In the molecule of the title compound, C₂₁H₁₅FN₄O₃, intramolecular C—H

O and C—H

F hydrogen bonds result in the formation of one six- and one five-membered ring. In the crystal structure, intermolecular C—H

O hydrogen bonds link the molecules into chains along the a axis. The packing is further stabilized by π–π interactions [centroid–centroid distance 3.632 (2) Å].

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807041967/hk2319sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807041967/hk2319Isup2.hkl Contains datablock I

CCDC reference: 636552

checkCIF report

Key indicators

Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.003 Å
R factor = 0.042
wR factor = 0.114
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 .......       0.98
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT154_ALERT_1_C The su's on the Cell Angles are Equal  (x 10000)        100 Deg.
PLAT180_ALERT_3_C Check Cell Rounding: # of Values Ending with 0 =          4
PLAT230_ALERT_2_C Hirshfeld Test Diff for    N2     -   N3      ..       5.39 su

Alert level G
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
   5 ALERT level C = Check and explain
   2 ALERT level G = General alerts; check

   4 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 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 crystal structure is reported here.

In the molecule of the title compound, (I), 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 ring system is essentially planar with a dihedral angle of 0.45 (1)° between triazole A (N1—N3/C10/C11) and benzene B (C10—C15) rings. Rings C (N4/C17—C21) and D (C1—C6) are oriented with respect to the benzotriazole system at dihedral angles of 87.82 (1)° and 0.78 (1)°, respectively, while the dihedral angle between them is 87.62 (1)°. The intramolecular C—H···O and C—H···F hydrogen bonds (Table 1) cause to the formation of one six- and one five-membered rings (Fig. 1).

In the crystal structure, the intermolecular C—H···O hydrogen bonds (Table 1), link the molecules into chains along the a axis (Fig. 2). The packing is further stabilized by π-π interactions involving the C1—C6 benzene rings: Cg3···Cg3^iv = 3.632 Å [symmetry code: (iv) 2 - x, -y, -1 - z, Cg3 is the centroid of th benzene ring].

Related literature top

For related literature, see: Han et al. (2007). For bond-length data, see: Allen et al. (1987).

Experimental top

The title compound was prepared according to the literature method (Han 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.

Structure description top

For related literature, see: Han et al. (2007). For bond-length data, 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 molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. A packing diagram for (I). Hydrogen bonds are shown as dashed lines.

3-(1H-Benzotriazol-1-yl)-1-(2-fluorobenzoyl)ethyl nicotinate 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 = 9.8423 (9) Å	Cell parameters from 2193 reflections
b = 9.9736 (10) Å	θ = 2.3–24.9°
c = 11.4000 (11) Å	µ = 0.10 mm⁻¹
α = 64.459 (1)°	T = 298 K
β = 67.157 (1)°	Block, yellow
γ = 76.313 (1)°	0.36 × 0.30 × 0.26 mm
V = 927.28 (15) Å³

Data collection top

Siemens SMART 1000 CCD area-detector diffractometer	3560 independent reflections
Radiation source: fine-focus sealed tube	2877 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.013
Detector resolution: 8.33 pixels mm^-1	θ_max = 26.0°, θ_min = 2.1°
ω scans	h = −12→6
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −12→12
T_min = 0.964, T_max = 0.974	l = −14→14
5202 measured reflections

Refinement top

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)] = 0.042	H-atom parameters constrained
wR(F²) = 0.114	w = 1/[σ²(F_o²) + (0.0541P)² + 0.1733P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max < 0.001
3560 reflections	Δρ_max = 0.14 e Å⁻³
263 parameters	Δρ_min = −0.18 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 1997), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.026 (3)

Crystal data top

C₂₁H₁₅FN₄O₃	γ = 76.313 (1)°
M_r = 390.37	V = 927.28 (15) Å³
Triclinic, P1	Z = 2
a = 9.8423 (9) Å	Mo Kα radiation
b = 9.9736 (10) Å	µ = 0.10 mm⁻¹
c = 11.4000 (11) Å	T = 298 K
α = 64.459 (1)°	0.36 × 0.30 × 0.26 mm
β = 67.157 (1)°

Data collection top

Siemens SMART 1000 CCD area-detector diffractometer	3560 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2877 reflections with I > 2σ(I)
T_min = 0.964, T_max = 0.974	R_int = 0.013
5202 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	0 restraints
wR(F²) = 0.114	H-atom parameters constrained
S = 1.05	Δρ_max = 0.14 e Å⁻³
3560 reflections	Δρ_min = −0.18 e Å⁻³
263 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	0.89959 (13)	0.26256 (12)	−0.41995 (10)	0.0754 (4)
O1	0.65340 (14)	−0.09185 (13)	−0.12652 (11)	0.0621 (3)
O2	0.72673 (11)	0.03294 (11)	−0.00182 (9)	0.0444 (3)
O3	0.94370 (14)	−0.10059 (14)	−0.05293 (12)	0.0660 (4)
N1	0.68866 (14)	0.36422 (13)	−0.13452 (12)	0.0433 (3)
N2	0.77269 (15)	0.47243 (14)	−0.24241 (14)	0.0539 (4)
N3	0.80732 (16)	0.55330 (15)	−0.19591 (15)	0.0592 (4)
N4	0.59613 (19)	−0.25912 (19)	0.39906 (15)	0.0761 (5)
C1	0.85535 (18)	0.17262 (17)	−0.45709 (16)	0.0487 (4)
C2	0.9011 (2)	0.2013 (2)	−0.59553 (17)	0.0607 (5)
H2B	0.9598	0.2790	−0.6596	0.073*
C3	0.8578 (2)	0.1122 (2)	−0.63630 (19)	0.0696 (5)
H3B	0.8860	0.1305	−0.7294	0.084*
C4	0.7734 (2)	−0.0035 (3)	−0.5410 (2)	0.0749 (6)
H4B	0.7447	−0.0634	−0.5697	0.090*
C5	0.73070 (19)	−0.0316 (2)	−0.40328 (18)	0.0592 (5)
H5A	0.6746	−0.1115	−0.3398	0.071*
C6	0.76984 (16)	0.05731 (16)	−0.35668 (15)	0.0420 (3)
C7	0.72116 (16)	0.01687 (16)	−0.20536 (15)	0.0416 (3)
C8	0.75139 (16)	0.11471 (15)	−0.14647 (14)	0.0406 (3)
H8A	0.8533	0.1432	−0.1937	0.049*
C9	0.64266 (17)	0.25315 (16)	−0.15857 (15)	0.0430 (3)
H9A	0.6338	0.2963	−0.2498	0.052*
H9B	0.5460	0.2246	−0.0924	0.052*
C10	0.66910 (16)	0.37656 (15)	−0.01425 (15)	0.0424 (3)
C11	0.74604 (18)	0.49795 (17)	−0.05488 (18)	0.0501 (4)
C12	0.7507 (2)	0.5446 (2)	0.0431 (2)	0.0672 (5)
H12A	0.8022	0.6253	0.0175	0.081*
C13	0.6769 (2)	0.4668 (2)	0.1771 (2)	0.0705 (5)
H13A	0.6782	0.4951	0.2444	0.085*
C14	0.5989 (2)	0.3452 (2)	0.21693 (19)	0.0648 (5)
H14A	0.5497	0.2954	0.3098	0.078*
C15	0.59284 (19)	0.29725 (18)	0.12321 (16)	0.0532 (4)
H15A	0.5409	0.2166	0.1497	0.064*
C16	0.82944 (17)	−0.07994 (16)	0.03048 (15)	0.0424 (3)
C17	0.78394 (16)	−0.17652 (15)	0.17859 (15)	0.0413 (3)
C18	0.64180 (19)	−0.16715 (19)	0.26721 (16)	0.0554 (4)
H18A	0.5741	−0.0926	0.2332	0.066*
C19	0.6977 (3)	−0.3626 (2)	0.44441 (19)	0.0743 (6)
H19A	0.6687	−0.4275	0.5360	0.089*
C20	0.8409 (2)	−0.37952 (19)	0.36566 (19)	0.0638 (5)
H20A	0.9073	−0.4527	0.4033	0.077*
C21	0.88514 (19)	−0.28663 (17)	0.22992 (17)	0.0528 (4)
H21A	0.9815	−0.2972	0.1731	0.063*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
F1	0.1104 (9)	0.0647 (7)	0.0472 (6)	−0.0452 (6)	−0.0100 (6)	−0.0125 (5)
O1	0.0804 (8)	0.0543 (7)	0.0468 (7)	−0.0304 (6)	−0.0125 (6)	−0.0097 (5)
O2	0.0525 (6)	0.0432 (6)	0.0325 (5)	0.0024 (5)	−0.0155 (5)	−0.0117 (4)
O3	0.0592 (7)	0.0693 (8)	0.0489 (7)	0.0123 (6)	−0.0107 (6)	−0.0192 (6)
N1	0.0509 (7)	0.0341 (6)	0.0392 (7)	−0.0053 (5)	−0.0133 (6)	−0.0090 (5)
N2	0.0618 (8)	0.0377 (7)	0.0470 (8)	−0.0077 (6)	−0.0109 (6)	−0.0067 (6)
N3	0.0655 (9)	0.0405 (7)	0.0637 (9)	−0.0134 (6)	−0.0132 (7)	−0.0150 (7)
N4	0.0797 (11)	0.0737 (11)	0.0437 (8)	0.0012 (9)	−0.0101 (8)	−0.0072 (8)
C1	0.0556 (9)	0.0452 (8)	0.0424 (8)	−0.0058 (7)	−0.0139 (7)	−0.0152 (7)
C2	0.0640 (11)	0.0623 (11)	0.0390 (9)	−0.0032 (9)	−0.0076 (8)	−0.0133 (8)
C3	0.0701 (12)	0.0952 (15)	0.0451 (10)	0.0061 (11)	−0.0163 (9)	−0.0368 (10)
C4	0.0765 (13)	0.1037 (16)	0.0658 (12)	−0.0143 (12)	−0.0180 (10)	−0.0523 (12)
C5	0.0573 (10)	0.0714 (11)	0.0567 (10)	−0.0162 (9)	−0.0099 (8)	−0.0334 (9)
C6	0.0418 (8)	0.0440 (8)	0.0396 (8)	−0.0017 (6)	−0.0125 (6)	−0.0169 (6)
C7	0.0432 (8)	0.0391 (7)	0.0398 (8)	−0.0059 (6)	−0.0135 (6)	−0.0112 (6)
C8	0.0461 (8)	0.0405 (8)	0.0317 (7)	−0.0070 (6)	−0.0117 (6)	−0.0098 (6)
C9	0.0489 (8)	0.0402 (8)	0.0398 (8)	−0.0040 (6)	−0.0180 (7)	−0.0116 (6)
C10	0.0435 (8)	0.0372 (7)	0.0462 (8)	0.0025 (6)	−0.0169 (7)	−0.0166 (6)
C11	0.0509 (9)	0.0380 (8)	0.0607 (10)	−0.0013 (7)	−0.0186 (8)	−0.0189 (7)
C12	0.0780 (13)	0.0521 (10)	0.0888 (15)	−0.0037 (9)	−0.0355 (11)	−0.0356 (10)
C13	0.0881 (14)	0.0685 (12)	0.0761 (14)	0.0069 (11)	−0.0382 (11)	−0.0431 (11)
C14	0.0776 (13)	0.0669 (11)	0.0501 (10)	0.0029 (10)	−0.0199 (9)	−0.0275 (9)
C15	0.0581 (10)	0.0512 (9)	0.0469 (9)	−0.0086 (8)	−0.0127 (8)	−0.0176 (7)
C16	0.0473 (8)	0.0415 (8)	0.0420 (8)	0.0001 (6)	−0.0176 (7)	−0.0185 (7)
C17	0.0503 (8)	0.0387 (7)	0.0411 (8)	−0.0015 (6)	−0.0210 (7)	−0.0163 (6)
C18	0.0585 (10)	0.0539 (9)	0.0438 (9)	0.0045 (8)	−0.0190 (8)	−0.0124 (7)
C19	0.1031 (17)	0.0611 (11)	0.0426 (10)	−0.0030 (11)	−0.0272 (11)	−0.0043 (8)
C20	0.0812 (13)	0.0489 (10)	0.0616 (11)	0.0050 (9)	−0.0412 (10)	−0.0109 (8)
C21	0.0559 (10)	0.0469 (9)	0.0571 (10)	0.0020 (7)	−0.0272 (8)	−0.0165 (8)

Geometric parameters (Å, º) top

F1—C1	1.3525 (19)	C8—H8A	0.9800
O1—C7	1.2103 (17)	C9—H9A	0.9700
O2—C8	1.4376 (16)	C9—H9B	0.9700
O2—C16	1.3482 (17)	C10—C11	1.390 (2)
O3—C16	1.2001 (18)	C10—C15	1.394 (2)
N1—N2	1.3600 (17)	C11—C12	1.401 (3)
N1—C9	1.4501 (19)	C12—H12A	0.9300
N1—C10	1.3643 (19)	C13—C12	1.359 (3)
N3—N2	1.299 (2)	C13—H13A	0.9300
N3—C11	1.376 (2)	C14—C15	1.370 (2)
N4—C19	1.336 (2)	C14—C13	1.401 (3)
C1—C2	1.377 (2)	C14—H14A	0.9300
C2—C3	1.369 (3)	C15—H15A	0.9300
C2—H2B	0.9300	C16—C17	1.481 (2)
C3—C4	1.369 (3)	C17—C18	1.382 (2)
C3—H3B	0.9300	C17—C21	1.386 (2)
C4—H4B	0.9300	C18—N4	1.336 (2)
C5—C4	1.372 (3)	C18—H18A	0.9300
C5—H5A	0.9300	C19—H19A	0.9300
C6—C1	1.384 (2)	C20—C19	1.363 (3)
C6—C5	1.394 (2)	C20—H20A	0.9300
C7—C6	1.489 (2)	C21—C20	1.369 (2)
C7—C8	1.533 (2)	C21—H21A	0.9300
C8—C9	1.524 (2)

C16—O2—C8	115.43 (11)	C8—C9—H9B	109.2
N2—N1—C10	109.94 (12)	H9A—C9—H9B	107.9
N2—N1—C9	119.71 (12)	N1—C10—C11	104.16 (13)
C10—N1—C9	130.22 (12)	N1—C10—C15	133.48 (14)
N3—N2—N1	108.89 (13)	C11—C10—C15	122.35 (15)
N2—N3—C11	108.38 (13)	N3—C11—C10	108.63 (14)
C18—N4—C19	116.17 (17)	N3—C11—C12	130.90 (16)
F1—C1—C2	116.89 (15)	C10—C11—C12	120.47 (16)
F1—C1—C6	119.52 (13)	C13—C12—C11	117.14 (17)
C2—C1—C6	123.58 (16)	C13—C12—H12A	121.4
C3—C2—C1	118.23 (17)	C11—C12—H12A	121.4
C3—C2—H2B	120.9	C12—C13—C14	121.96 (18)
C1—C2—H2B	120.9	C12—C13—H13A	119.0
C2—C3—C4	120.45 (17)	C14—C13—H13A	119.0
C2—C3—H3B	119.8	C15—C14—C13	122.02 (18)
C4—C3—H3B	119.8	C15—C14—H14A	119.0
C3—C4—C5	120.44 (18)	C13—C14—H14A	119.0
C3—C4—H4B	119.8	C14—C15—C10	116.06 (16)
C5—C4—H4B	119.8	C14—C15—H15A	122.0
C4—C5—C6	121.31 (17)	C10—C15—H15A	122.0
C4—C5—H5A	119.3	O3—C16—O2	123.21 (14)
C6—C5—H5A	119.3	O3—C16—C17	124.15 (14)
C1—C6—C5	115.97 (14)	O2—C16—C17	112.63 (12)
C1—C6—C7	126.34 (14)	C18—C17—C21	118.07 (14)
C5—C6—C7	117.65 (14)	C18—C17—C16	122.75 (13)
O1—C7—C6	120.59 (13)	C21—C17—C16	119.08 (14)
O1—C7—C8	118.64 (13)	N4—C18—C17	123.69 (15)
C6—C7—C8	120.73 (12)	N4—C18—H18A	118.2
O2—C8—C9	106.13 (11)	C17—C18—H18A	118.2
O2—C8—C7	108.81 (11)	N4—C19—C20	124.51 (17)
C9—C8—C7	110.90 (12)	N4—C19—H19A	117.7
O2—C8—H8A	110.3	C20—C19—H19A	117.7
C9—C8—H8A	110.3	C19—C20—C21	118.61 (16)
C7—C8—H8A	110.3	C19—C20—H20A	120.7
N1—C9—C8	112.17 (12)	C21—C20—H20A	120.7
N1—C9—H9A	109.2	C20—C21—C17	118.91 (16)
C8—C9—H9A	109.2	C20—C21—H21A	120.5
N1—C9—H9B	109.2	C17—C21—H21A	120.5

C16—O2—C8—C9	−168.65 (11)	C8—C7—C6—C5	−176.13 (14)
C16—O2—C8—C7	71.94 (15)	O1—C7—C8—O2	15.96 (19)
C8—O2—C16—O3	9.4 (2)	C6—C7—C8—O2	−165.99 (12)
C8—O2—C16—C17	−169.32 (11)	O1—C7—C8—C9	−100.42 (16)
C10—N1—N2—N3	−0.08 (17)	C6—C7—C8—C9	77.63 (16)
C9—N1—N2—N3	−176.40 (12)	O2—C8—C9—N1	75.59 (14)
N2—N1—C9—C8	91.87 (15)	C7—C8—C9—N1	−166.39 (11)
C10—N1—C9—C8	−83.59 (18)	N1—C10—C11—N3	0.26 (16)
N2—N1—C10—C11	−0.11 (15)	C15—C10—C11—N3	−179.16 (14)
C9—N1—C10—C11	175.70 (14)	N1—C10—C11—C12	−179.94 (14)
N2—N1—C10—C15	179.21 (16)	C15—C10—C11—C12	0.6 (2)
C9—N1—C10—C15	−5.0 (3)	N1—C10—C15—C14	−179.72 (16)
C11—N3—N2—N1	0.24 (17)	C11—C10—C15—C14	−0.5 (2)
N2—N3—C11—C10	−0.32 (18)	N3—C11—C12—C13	179.43 (17)
N2—N3—C11—C12	179.91 (17)	C10—C11—C12—C13	−0.3 (3)
C18—N4—C19—C20	−0.4 (3)	C14—C13—C12—C11	−0.1 (3)
F1—C1—C2—C3	−179.88 (15)	C13—C14—C15—C10	0.1 (3)
C6—C1—C2—C3	1.0 (3)	C15—C14—C13—C12	0.2 (3)
C1—C2—C3—C4	−1.1 (3)	C18—C17—C21—C20	−0.8 (2)
C2—C3—C4—C5	0.1 (3)	C16—C17—C21—C20	−177.42 (15)
C6—C5—C4—C3	0.9 (3)	C21—C17—C18—N4	−0.7 (3)
C5—C6—C1—F1	−179.08 (14)	C16—C17—C18—N4	175.74 (16)
C7—C6—C1—F1	−1.4 (2)	O3—C16—C17—C18	−167.62 (16)
C5—C6—C1—C2	0.0 (2)	O2—C16—C17—C18	11.0 (2)
C7—C6—C1—C2	177.67 (15)	O3—C16—C17—C21	8.8 (2)
C1—C6—C5—C4	−1.0 (3)	O2—C16—C17—C21	−172.55 (13)
C7—C6—C5—C4	−178.86 (17)	C17—C18—N4—C19	1.3 (3)
O1—C7—C6—C1	−175.75 (15)	C21—C20—C19—N4	−1.1 (3)
C8—C7—C6—C1	6.2 (2)	C17—C21—C20—C19	1.7 (3)
O1—C7—C6—C5	1.9 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3B···O3ⁱ	0.93	2.50	3.355 (2)	154
C8—H8A···F1	0.98	2.23	2.747 (2)	112
C9—H9B···O1ⁱⁱ	0.97	2.53	3.464 (2)	161
C18—H18A···O2	0.93	2.43	2.758 (2)	101

Symmetry codes: (i) −x+2, −y, −z−1; (ii) −x+1, −y, −z.

Experimental details

Crystal data
Chemical formula	C₂₁H₁₅FN₄O₃
M_r	390.37
Crystal system, space group	Triclinic, P1
Temperature (K)	298
a, b, c (Å)	9.8423 (9), 9.9736 (10), 11.4000 (11)
α, β, γ (°)	64.459 (1), 67.157 (1), 76.313 (1)
V (Å³)	927.28 (15)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.36 × 0.30 × 0.26

Data collection
Diffractometer	Siemens SMART 1000 CCD area-detector
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.964, 0.974
No. of measured, independent and observed [I > 2σ(I)] reflections	5202, 3560, 2877
R_int	0.013
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.114, 1.05
No. of reflections	3560
No. of parameters	263
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).