2-(1H-Benzotriazol-1-yl)-1-(4-fluoro­benzo­yl)ethyl nicotinate

Bi, S.; Luo, H.; Zeng, W.-L.; Wan, J.

doi:10.1107/S1600536807054487

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2-(1H-Benzotriazol-1-yl)-1-(4-fluorobenzoyl)ethyl nicotinate

S. Bi, H. Luo, W.-L. Zeng and J. Wan

There are two molecules in the asymmetric unit of the title compound, C₂₁H₁₅FN₄O₃. In the crystal structure, two intramolecular C—H

O hydrogen bonds form two five-membered rings. The molecules are linked into infinite chains along the b axis by intermolecular C—H

O hydrogen bonds, and further linked by C—H

N interactions along the a axis. The packing is further stabilized by C—H

π interactions.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807054487/at2452sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807054487/at2452Isup2.hkl Contains datablock I

CCDC reference: 635803

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.005 Å
R factor = 0.057
wR factor = 0.143
Data-to-parameter ratio = 13.6

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT230_ALERT_2_B Hirshfeld Test Diff for    C19    -   C20     ..       8.60 su

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)        200 Deg.
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.26 Ratio
PLAT220_ALERT_2_C Large Non-Solvent    N     Ueq(max)/Ueq(min) ...       2.65 Ratio
PLAT230_ALERT_2_C Hirshfeld Test Diff for    N4     -   C21     ..       5.39 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C6     -   C7      ..       6.18 su
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         N4
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C17
PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...          5
PLAT432_ALERT_2_C Short Inter X...Y Contact  O3A    ..  C9      ..       2.99 Ang.
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          7

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
PLAT793_ALERT_1_G Check the Absolute Configuration of C8A    = ...          R

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

   6 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   8 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
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Comment top

Recently we have reported the structure of 3-(1H-benzotriazol-1-yl)-1-(4-fluorophenyl)-1-oxopropan-2-yl 2,4-dichlorobenzoate (II) (Bi et al., 2007). As part of our ongoing studies on new triazole compounds with higher bioactivity, the title compound, (I), was synthesized and its structure is shown here.

The asymmetric unit of (I) contains two molecules A and B (Fig. 1). All bond lengths and angles are within normal ranges (Allen et al., 1987) and are comparable with those in the related compound, (II). The benzotriazole units, N1—N3/C10/C15 and N1A—N3A/C10A/C15A, are essentially planar, with dihedral angles of 0.29 (2) and 1.13 (1)°, respectively. The dihedral angles between rings A(C1—C6), B(N4/C17—C21), C(C1A—C6A) and D(N4A/C17A—C21A) are A/B = 78.97 (2)° and C/D = 72.49 (1)°. The dihedral angles between the benzotriazole units E(N1—N3/C10—C15) and F(N1A—N3A/C10A—C15A) and A, B, C and D are E/A = 22.29 (1)°, E/B = 89.41 (2)°, F/C = 6.24 (1)° and F/D = 69.53 (1)°, respectively. Intramolecular C18—H18B···O2 and C21A—H21A···O3A interactions (Table 2) result in the information of two five-numbered rings.

In the crystal structure, molecules are linked into infinite chains along the b axis by C—H···O intermolecular hydrogen bonds (Table 2). The chains are also linked by C—H···N interactions along a axis (Table 2). The packing is further stabilized by C—H···π interactions (Table 2).

Related literature top

For related literature, see: Bi et al., (2007); Allen et al. (1987).

Experimental top

The title compound was prepared according to the literature method of Bi et al. (2007). Single crystals suitable for X-ray diffraction were obtained by slow evaporation of an ethyl acetate solution at room temperature over a period of five days.

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, 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 a axis. Hydrogen bonds are indicated by dashed lines.

2-(1H-Benzotriazol-1-yl)-1-(4-fluorobenzoyl)ethyl nicotinate top

Crystal data top

C₂₁H₁₅FN₄O₃	Z = 4
M_r = 390.37	F(000) = 808
Triclinic, P1	D_x = 1.401 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.6707 (10) Å	Cell parameters from 3056 reflections
b = 10.762 (1) Å	θ = 2.4–21.2°
c = 17.2223 (17) Å	µ = 0.10 mm⁻¹
α = 81.199 (2)°	T = 293 K
β = 72.270 (2)°	Plate, yellow
γ = 81.439 (2)°	0.30 × 0.23 × 0.09 mm
V = 1850.6 (3) Å³

Data collection top

Siemens SMART 1000 CCD area detector diffractometer	7131 independent reflections
Radiation source: fine-focus sealed tube	4047 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.023
Detector resolution: 8.33 pixels mm^-1	θ_max = 26.0°, θ_min = 1.9°
ω scans	h = −13→8
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −13→10
T_min = 0.970, T_max = 0.991	l = −21→21
10479 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)] = 0.057	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.143	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.0553P)² + 0.1218P] where P = (F_o² + 2F_c²)/3
7131 reflections	(Δ/σ)_max < 0.001
523 parameters	Δρ_max = 0.19 e Å⁻³
0 restraints	Δρ_min = −0.17 e Å⁻³

Crystal data top

C₂₁H₁₅FN₄O₃	γ = 81.439 (2)°
M_r = 390.37	V = 1850.6 (3) Å³
Triclinic, P1	Z = 4
a = 10.6707 (10) Å	Mo Kα radiation
b = 10.762 (1) Å	µ = 0.10 mm⁻¹
c = 17.2223 (17) Å	T = 293 K
α = 81.199 (2)°	0.30 × 0.23 × 0.09 mm
β = 72.270 (2)°

Data collection top

Siemens SMART 1000 CCD area detector diffractometer	7131 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	4047 reflections with I > 2σ(I)
T_min = 0.970, T_max = 0.991	R_int = 0.023
10479 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.057	0 restraints
wR(F²) = 0.143	H-atom parameters constrained
S = 1.00	Δρ_max = 0.19 e Å⁻³
7131 reflections	Δρ_min = −0.17 e Å⁻³
523 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
O2A	0.39562 (16)	0.09554 (16)	0.41047 (10)	0.0512 (4)
O3A	0.47972 (17)	0.13222 (18)	0.27434 (11)	0.0621 (5)
N1A	0.1189 (2)	0.1451 (2)	0.51728 (12)	0.0512 (5)
O1A	0.40691 (19)	−0.13192 (18)	0.35481 (12)	0.0706 (6)
C16A	0.4876 (3)	0.1366 (2)	0.34208 (16)	0.0480 (6)
C11A	0.0596 (2)	0.3109 (2)	0.58218 (16)	0.0525 (7)
N2A	0.0131 (2)	0.2112 (2)	0.49600 (13)	0.0585 (6)
C8A	0.2799 (2)	0.0603 (2)	0.39568 (15)	0.0493 (6)
H8AA	0.2414	0.1311	0.3641	0.059*
N3A	−0.0237 (2)	0.3117 (2)	0.53464 (15)	0.0642 (6)
C17A	0.5965 (2)	0.1878 (2)	0.35919 (15)	0.0460 (6)
C7A	0.3126 (3)	−0.0571 (3)	0.34981 (16)	0.0528 (7)
C18A	0.5934 (3)	0.2156 (2)	0.43539 (16)	0.0556 (7)
H18A	0.5215	0.1998	0.4810	0.067*
C5A	0.1187 (3)	0.0127 (3)	0.29250 (17)	0.0615 (8)
H5AA	0.1014	0.0867	0.3174	0.074*
F1A	−0.0079 (2)	−0.1344 (2)	0.16306 (12)	0.1072 (7)
C10A	0.1511 (2)	0.2044 (2)	0.57143 (15)	0.0479 (6)
C6A	0.2225 (3)	−0.0757 (2)	0.30273 (15)	0.0512 (7)
C9A	0.1824 (3)	0.0321 (2)	0.47910 (16)	0.0580 (7)
H9AA	0.1151	−0.0143	0.4733	0.070*
H9AB	0.2285	−0.0216	0.5147	0.070*
C4A	0.0404 (3)	−0.0073 (3)	0.24585 (19)	0.0719 (9)
H4AA	−0.0290	0.0525	0.2389	0.086*
C21A	0.7059 (3)	0.2135 (3)	0.29363 (18)	0.0681 (8)
H21A	0.7067	0.1961	0.2422	0.082*
C1A	0.2441 (3)	−0.1856 (3)	0.26559 (17)	0.0652 (8)
H1AA	0.3126	−0.2467	0.2724	0.078*
N4A	0.8100 (3)	0.2616 (3)	0.29966 (17)	0.0844 (8)
C3A	0.0671 (3)	−0.1165 (3)	0.21022 (18)	0.0712 (9)
C19A	0.6996 (3)	0.2675 (3)	0.4422 (2)	0.0651 (8)
H19A	0.7000	0.2890	0.4924	0.078*
C15A	0.2475 (3)	0.1752 (3)	0.61255 (17)	0.0621 (8)
H15A	0.3081	0.1033	0.6051	0.074*
C20A	0.8048 (3)	0.2870 (3)	0.3736 (2)	0.0742 (9)
H20A	0.8768	0.3201	0.3793	0.089*
C2A	0.1669 (3)	−0.2064 (3)	0.21896 (19)	0.0751 (9)
H2AB	0.1827	−0.2803	0.1940	0.090*
C12A	0.0621 (3)	0.3950 (3)	0.63594 (19)	0.0727 (9)
H12A	0.0020	0.4672	0.6438	0.087*
C14A	0.2474 (3)	0.2590 (3)	0.66453 (18)	0.0749 (9)
H14A	0.3102	0.2439	0.6932	0.090*
C34	0.1558 (3)	0.3666 (3)	0.67605 (19)	0.0808 (10)
H34A	0.1594	0.4206	0.7125	0.097*
O2	0.18536 (17)	0.34784 (17)	0.12407 (10)	0.0577 (5)
O1	0.15018 (19)	0.31998 (18)	0.28409 (11)	0.0650 (5)
F1	0.53088 (17)	0.56755 (17)	0.41166 (10)	0.0858 (5)
C6	0.3252 (2)	0.4266 (2)	0.28601 (15)	0.0448 (6)
N1	0.4293 (2)	0.2424 (2)	0.04113 (13)	0.0565 (6)
C5	0.4421 (3)	0.4800 (2)	0.24456 (15)	0.0545 (7)
H5A	0.4736	0.4836	0.1877	0.065*
C3	0.4628 (3)	0.5216 (3)	0.36979 (17)	0.0571 (7)
O3	0.0886 (2)	0.5393 (2)	0.15805 (13)	0.0801 (6)
C8	0.2941 (2)	0.3699 (3)	0.15120 (15)	0.0532 (7)
H8A	0.3282	0.4500	0.1239	0.064*
C16	0.0848 (3)	0.4427 (3)	0.13211 (16)	0.0590 (7)
C1	0.2796 (3)	0.4238 (2)	0.37101 (15)	0.0536 (7)
H1A	0.2015	0.3889	0.3995	0.064*
C7	0.2485 (3)	0.3702 (2)	0.24472 (16)	0.0499 (7)
N2	0.5100 (2)	0.3179 (2)	−0.01670 (15)	0.0690 (7)
C9	0.3984 (3)	0.2588 (3)	0.12730 (15)	0.0615 (8)
H9A	0.4784	0.2721	0.1390	0.074*
H9B	0.3668	0.1821	0.1604	0.074*
C4	0.5110 (3)	0.5272 (3)	0.28666 (17)	0.0600 (7)
H4A	0.5893	0.5624	0.2590	0.072*
C10	0.3852 (3)	0.1612 (3)	0.00545 (16)	0.0570 (7)
C17	−0.0236 (3)	0.4136 (3)	0.10463 (16)	0.0646 (8)
C2	0.3481 (3)	0.4716 (3)	0.41365 (16)	0.0588 (7)
H2B	0.3174	0.4699	0.4704	0.071*
N3	0.5184 (3)	0.2877 (3)	−0.08884 (15)	0.0767 (8)
C11	0.4422 (3)	0.1907 (3)	−0.07776 (17)	0.0641 (8)
C18	−0.0262 (4)	0.3000 (4)	0.0795 (2)	0.1011 (12)
H18B	0.0442	0.2376	0.0795	0.121*
C21	−0.1282 (3)	0.5052 (4)	0.10457 (19)	0.0964 (12)
H21B	−0.1291	0.5831	0.1219	0.116*
C12	0.4186 (4)	0.1241 (4)	−0.1343 (2)	0.0943 (12)
H12B	0.4570	0.1421	−0.1905	0.113*
N4	−0.2318 (4)	0.4816 (6)	0.0788 (2)	0.1501 (18)
C15	0.3031 (3)	0.0657 (3)	0.0367 (2)	0.0856 (10)
H15B	0.2657	0.0461	0.0928	0.103*
C13	0.3367 (4)	0.0316 (5)	−0.1036 (3)	0.1182 (16)
H13A	0.3176	−0.0134	−0.1398	0.142*
C20	−0.2216 (6)	0.3631 (8)	0.0530 (3)	0.146 (3)
H20B	−0.2883	0.3459	0.0331	0.176*
C14	0.2805 (4)	0.0020 (4)	−0.0195 (3)	0.1170 (15)
H14B	0.2261	−0.0628	−0.0012	0.140*
C19	−0.1251 (5)	0.2755 (5)	0.0551 (3)	0.1293 (18)
H19B	−0.1254	0.1965	0.0396	0.155*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O2A	0.0482 (11)	0.0598 (12)	0.0476 (10)	−0.0126 (9)	−0.0118 (9)	−0.0095 (8)
O3A	0.0595 (12)	0.0841 (14)	0.0464 (11)	−0.0101 (10)	−0.0189 (9)	−0.0090 (10)
N1A	0.0438 (13)	0.0532 (14)	0.0574 (14)	−0.0048 (11)	−0.0114 (11)	−0.0157 (11)
O1A	0.0702 (14)	0.0612 (13)	0.0848 (15)	0.0125 (11)	−0.0307 (11)	−0.0234 (11)
C16A	0.0487 (16)	0.0478 (16)	0.0467 (16)	−0.0022 (12)	−0.0131 (14)	−0.0070 (12)
C11A	0.0412 (15)	0.0570 (18)	0.0563 (16)	−0.0048 (13)	−0.0043 (13)	−0.0181 (13)
N2A	0.0462 (14)	0.0699 (16)	0.0617 (15)	−0.0075 (12)	−0.0149 (12)	−0.0144 (12)
C8A	0.0421 (15)	0.0527 (16)	0.0558 (16)	−0.0070 (12)	−0.0137 (13)	−0.0134 (13)
N3A	0.0520 (15)	0.0661 (17)	0.0741 (16)	−0.0007 (12)	−0.0150 (13)	−0.0192 (13)
C17A	0.0428 (15)	0.0439 (15)	0.0513 (15)	−0.0023 (12)	−0.0152 (13)	−0.0049 (12)
C7A	0.0485 (17)	0.0496 (17)	0.0569 (17)	−0.0028 (14)	−0.0094 (14)	−0.0106 (13)
C18A	0.0538 (17)	0.0585 (18)	0.0563 (17)	−0.0077 (14)	−0.0176 (14)	−0.0075 (13)
C5A	0.0561 (18)	0.0599 (19)	0.074 (2)	−0.0049 (15)	−0.0195 (16)	−0.0258 (15)
F1A	0.1093 (16)	0.1380 (18)	0.1016 (15)	−0.0357 (13)	−0.0512 (13)	−0.0319 (13)
C10A	0.0431 (15)	0.0533 (17)	0.0476 (15)	−0.0129 (13)	−0.0088 (12)	−0.0078 (12)
C6A	0.0487 (16)	0.0480 (16)	0.0565 (16)	−0.0082 (13)	−0.0092 (13)	−0.0140 (13)
C9A	0.0505 (17)	0.0536 (17)	0.0683 (19)	−0.0106 (13)	−0.0067 (14)	−0.0192 (14)
C4A	0.059 (2)	0.079 (2)	0.084 (2)	−0.0080 (16)	−0.0262 (17)	−0.0186 (18)
C21A	0.058 (2)	0.089 (2)	0.0608 (19)	−0.0156 (17)	−0.0179 (16)	−0.0089 (16)
C1A	0.069 (2)	0.0535 (18)	0.075 (2)	−0.0069 (15)	−0.0175 (16)	−0.0217 (15)
N4A	0.0597 (17)	0.114 (2)	0.084 (2)	−0.0296 (16)	−0.0209 (15)	−0.0053 (17)
C3A	0.069 (2)	0.091 (3)	0.065 (2)	−0.0268 (19)	−0.0231 (17)	−0.0172 (18)
C19A	0.071 (2)	0.0580 (19)	0.078 (2)	−0.0090 (16)	−0.0361 (19)	−0.0124 (16)
C15A	0.0603 (19)	0.0616 (19)	0.0675 (19)	−0.0084 (14)	−0.0234 (16)	−0.0048 (15)
C20A	0.064 (2)	0.068 (2)	0.102 (3)	−0.0192 (16)	−0.041 (2)	0.0037 (19)
C2A	0.085 (2)	0.067 (2)	0.082 (2)	−0.0195 (19)	−0.0213 (19)	−0.0316 (17)
C12A	0.060 (2)	0.073 (2)	0.083 (2)	−0.0047 (16)	−0.0072 (17)	−0.0351 (18)
C14A	0.069 (2)	0.098 (3)	0.068 (2)	−0.0207 (19)	−0.0296 (17)	−0.0106 (19)
C34	0.078 (2)	0.095 (3)	0.075 (2)	−0.021 (2)	−0.0118 (19)	−0.0384 (19)
O2	0.0588 (12)	0.0638 (12)	0.0590 (11)	0.0043 (10)	−0.0273 (10)	−0.0222 (9)
O1	0.0639 (13)	0.0782 (14)	0.0583 (12)	−0.0212 (11)	−0.0179 (10)	−0.0111 (10)
F1	0.0943 (13)	0.1025 (14)	0.0828 (12)	−0.0319 (10)	−0.0438 (11)	−0.0190 (10)
C6	0.0481 (16)	0.0450 (15)	0.0453 (15)	−0.0041 (12)	−0.0173 (13)	−0.0101 (12)
N1	0.0498 (14)	0.0728 (16)	0.0466 (13)	−0.0011 (12)	−0.0121 (11)	−0.0150 (12)
C5	0.0596 (18)	0.0615 (18)	0.0427 (15)	−0.0092 (14)	−0.0119 (14)	−0.0094 (13)
C3	0.0638 (19)	0.0563 (18)	0.0631 (19)	−0.0077 (15)	−0.0319 (16)	−0.0142 (14)
O3	0.0834 (15)	0.0709 (15)	0.0931 (16)	0.0114 (12)	−0.0342 (13)	−0.0319 (12)
C8	0.0544 (17)	0.0633 (18)	0.0486 (15)	−0.0025 (14)	−0.0221 (13)	−0.0158 (13)
C16	0.0591 (19)	0.068 (2)	0.0495 (16)	0.0007 (16)	−0.0164 (14)	−0.0126 (15)
C1	0.0526 (17)	0.0604 (18)	0.0480 (16)	−0.0104 (13)	−0.0110 (13)	−0.0101 (13)
C7	0.0506 (17)	0.0494 (16)	0.0492 (16)	−0.0005 (13)	−0.0143 (14)	−0.0086 (13)
N2	0.0590 (16)	0.0821 (19)	0.0634 (17)	−0.0071 (14)	−0.0114 (14)	−0.0141 (14)
C9	0.0636 (19)	0.077 (2)	0.0457 (16)	0.0067 (15)	−0.0206 (14)	−0.0165 (14)
C4	0.0548 (18)	0.0674 (19)	0.0613 (18)	−0.0196 (14)	−0.0154 (15)	−0.0084 (15)
C10	0.0533 (18)	0.0668 (19)	0.0485 (16)	0.0036 (15)	−0.0096 (14)	−0.0201 (14)
C17	0.0519 (19)	0.093 (2)	0.0476 (16)	−0.0052 (17)	−0.0169 (14)	−0.0018 (16)
C2	0.067 (2)	0.070 (2)	0.0422 (15)	−0.0093 (16)	−0.0165 (15)	−0.0134 (14)
N3	0.0768 (19)	0.091 (2)	0.0516 (16)	−0.0022 (16)	−0.0080 (14)	−0.0053 (14)
C11	0.0580 (19)	0.082 (2)	0.0498 (17)	0.0051 (17)	−0.0124 (15)	−0.0186 (16)
C18	0.090 (3)	0.120 (3)	0.116 (3)	−0.023 (2)	−0.055 (2)	−0.019 (3)
C21	0.057 (2)	0.154 (4)	0.071 (2)	0.013 (2)	−0.0203 (18)	−0.008 (2)
C12	0.093 (3)	0.132 (4)	0.060 (2)	0.008 (2)	−0.020 (2)	−0.040 (2)
N4	0.068 (2)	0.273 (6)	0.095 (3)	−0.013 (3)	−0.024 (2)	0.018 (3)
C15	0.088 (3)	0.085 (3)	0.075 (2)	−0.023 (2)	0.0029 (19)	−0.0255 (19)
C13	0.103 (3)	0.155 (4)	0.112 (4)	−0.006 (3)	−0.027 (3)	−0.081 (3)
C20	0.089 (4)	0.275 (9)	0.093 (4)	−0.074 (5)	−0.041 (3)	0.008 (4)
C14	0.107 (3)	0.113 (3)	0.133 (4)	−0.034 (2)	−0.003 (3)	−0.065 (3)
C19	0.099 (3)	0.162 (5)	0.168 (5)	−0.046 (3)	−0.077 (3)	−0.034 (3)

Geometric parameters (Å, º) top

O2A—C16A	1.346 (3)	O2—C16	1.356 (3)
O2A—C8A	1.447 (3)	O2—C8	1.438 (3)
O3A—C16A	1.204 (3)	O1—C7	1.215 (3)
N1A—C10A	1.356 (3)	F1—C3	1.352 (3)
N1A—N2A	1.360 (3)	C6—C1	1.392 (3)
N1A—C9A	1.449 (3)	C6—C5	1.393 (3)
O1A—C7A	1.208 (3)	C6—C7	1.476 (3)
C16A—C17A	1.479 (3)	N1—C10	1.351 (3)
C11A—N3A	1.378 (3)	N1—N2	1.353 (3)
C11A—C10A	1.387 (3)	N1—C9	1.451 (3)
C11A—C12A	1.399 (3)	C5—C4	1.369 (3)
N2A—N3A	1.305 (3)	C5—H5A	0.9300
C8A—C9A	1.513 (3)	C3—C4	1.361 (4)
C8A—C7A	1.532 (3)	C3—C2	1.366 (4)
C8A—H8AA	0.9800	O3—C16	1.204 (3)
C17A—C18A	1.380 (3)	C8—C9	1.521 (3)
C17A—C21A	1.383 (4)	C8—C7	1.534 (3)
C7A—C6A	1.485 (3)	C8—H8A	0.9800
C18A—C19A	1.378 (3)	C16—C17	1.465 (4)
C18A—H18A	0.9300	C1—C2	1.376 (3)
C5A—C4A	1.380 (3)	C1—H1A	0.9300
C5A—C6A	1.385 (3)	N2—N3	1.305 (3)
C5A—H5AA	0.9300	C9—H9A	0.9700
F1A—C3A	1.352 (3)	C9—H9B	0.9700
C10A—C15A	1.392 (3)	C4—H4A	0.9300
C6A—C1A	1.386 (3)	C10—C11	1.383 (4)
C9A—H9AA	0.9700	C10—C15	1.388 (4)
C9A—H9AB	0.9700	C17—C18	1.365 (4)
C4A—C3A	1.361 (4)	C17—C21	1.374 (4)
C4A—H4AA	0.9300	C2—H2B	0.9300
C21A—N4A	1.330 (3)	N3—C11	1.373 (4)
C21A—H21A	0.9300	C11—C12	1.394 (4)
C1A—C2A	1.374 (4)	C18—C19	1.323 (4)
C1A—H1AA	0.9300	C18—H18B	0.9300
N4A—C20A	1.326 (4)	C21—N4	1.378 (5)
C3A—C2A	1.356 (4)	C21—H21B	0.9300
C19A—C20A	1.374 (4)	C12—C13	1.360 (5)
C19A—H19A	0.9300	C12—H12B	0.9300
C15A—C14A	1.364 (4)	N4—C20	1.392 (7)
C15A—H15A	0.9300	C15—C14	1.362 (4)
C20A—H20A	0.9300	C15—H15B	0.9300
C2A—H2AB	0.9300	C13—C14	1.395 (6)
C12A—C34	1.355 (4)	C13—H13A	0.9300
C12A—H12A	0.9300	C20—C19	1.294 (7)
C14A—C34	1.397 (4)	C20—H20B	0.9300
C14A—H14A	0.9300	C14—H14B	0.9300
C34—H34A	0.9300	C19—H19B	0.9300

C16A—O2A—C8A	114.21 (19)	C16—O2—C8	115.0 (2)
C10A—N1A—N2A	110.4 (2)	C1—C6—C5	118.4 (2)
C10A—N1A—C9A	130.2 (2)	C1—C6—C7	118.1 (2)
N2A—N1A—C9A	119.4 (2)	C5—C6—C7	123.4 (2)
O3A—C16A—O2A	122.4 (2)	C10—N1—N2	110.3 (2)
O3A—C16A—C17A	124.3 (2)	C10—N1—C9	129.4 (2)
O2A—C16A—C17A	113.2 (2)	N2—N1—C9	120.3 (2)
N3A—C11A—C10A	109.1 (2)	C4—C5—C6	120.7 (2)
N3A—C11A—C12A	130.9 (3)	C4—C5—H5A	119.7
C10A—C11A—C12A	120.0 (3)	C6—C5—H5A	119.7
N3A—N2A—N1A	108.8 (2)	F1—C3—C4	118.9 (3)
O2A—C8A—C9A	106.4 (2)	F1—C3—C2	117.8 (2)
O2A—C8A—C7A	111.9 (2)	C4—C3—C2	123.3 (2)
C9A—C8A—C7A	109.5 (2)	O2—C8—C9	104.8 (2)
O2A—C8A—H8AA	109.7	O2—C8—C7	109.3 (2)
C9A—C8A—H8AA	109.7	C9—C8—C7	110.3 (2)
C7A—C8A—H8AA	109.7	O2—C8—H8A	110.7
N2A—N3A—C11A	107.7 (2)	C9—C8—H8A	110.7
C18A—C17A—C21A	118.3 (3)	C7—C8—H8A	110.7
C18A—C17A—C16A	124.2 (2)	O3—C16—O2	122.1 (3)
C21A—C17A—C16A	117.4 (2)	O3—C16—C17	125.5 (3)
O1A—C7A—C6A	122.6 (2)	O2—C16—C17	112.4 (3)
O1A—C7A—C8A	119.8 (2)	C2—C1—C6	121.2 (3)
C6A—C7A—C8A	117.6 (2)	C2—C1—H1A	119.4
C19A—C18A—C17A	118.3 (3)	C6—C1—H1A	119.4
C19A—C18A—H18A	120.9	O1—C7—C6	120.8 (2)
C17A—C18A—H18A	120.9	O1—C7—C8	118.6 (2)
C4A—C5A—C6A	121.0 (3)	C6—C7—C8	120.5 (2)
C4A—C5A—H5AA	119.5	N3—N2—N1	108.5 (2)
C6A—C5A—H5AA	119.5	N1—C9—C8	112.3 (2)
N1A—C10A—C11A	104.1 (2)	N1—C9—H9A	109.1
N1A—C10A—C15A	133.0 (2)	C8—C9—H9A	109.1
C11A—C10A—C15A	122.9 (2)	N1—C9—H9B	109.1
C5A—C6A—C1A	117.9 (2)	C8—C9—H9B	109.1
C5A—C6A—C7A	123.2 (2)	H9A—C9—H9B	107.9
C1A—C6A—C7A	118.9 (2)	C3—C4—C5	118.7 (3)
N1A—C9A—C8A	113.0 (2)	C3—C4—H4A	120.7
N1A—C9A—H9AA	109.0	C5—C4—H4A	120.7
C8A—C9A—H9AA	109.0	N1—C10—C11	104.6 (3)
N1A—C9A—H9AB	109.0	N1—C10—C15	133.0 (3)
C8A—C9A—H9AB	109.0	C11—C10—C15	122.5 (3)
H9AA—C9A—H9AB	107.8	C18—C17—C21	118.4 (3)
C3A—C4A—C5A	118.5 (3)	C18—C17—C16	123.2 (3)
C3A—C4A—H4AA	120.8	C21—C17—C16	118.3 (3)
C5A—C4A—H4AA	120.8	C3—C2—C1	117.8 (2)
N4A—C21A—C17A	124.0 (3)	C3—C2—H2B	121.1
N4A—C21A—H21A	118.0	C1—C2—H2B	121.1
C17A—C21A—H21A	118.0	N2—N3—C11	108.1 (2)
C2A—C1A—C6A	121.6 (3)	N3—C11—C10	108.5 (3)
C2A—C1A—H1AA	119.2	N3—C11—C12	131.0 (3)
C6A—C1A—H1AA	119.2	C10—C11—C12	120.5 (3)
C20A—N4A—C21A	116.5 (3)	C19—C18—C17	122.3 (4)
F1A—C3A—C2A	119.0 (3)	C19—C18—H18B	118.8
F1A—C3A—C4A	118.3 (3)	C17—C18—H18B	118.8
C2A—C3A—C4A	122.8 (3)	C17—C21—N4	120.0 (4)
C20A—C19A—C18A	118.9 (3)	C17—C21—H21B	120.0
C20A—C19A—H19A	120.6	N4—C21—H21B	120.0
C18A—C19A—H19A	120.6	C13—C12—C11	116.9 (4)
C14A—C15A—C10A	115.7 (3)	C13—C12—H12B	121.6
C14A—C15A—H15A	122.2	C11—C12—H12B	121.6
C10A—C15A—H15A	122.2	C21—N4—C20	116.2 (5)
N4A—C20A—C19A	124.0 (3)	C14—C15—C10	116.3 (3)
N4A—C20A—H20A	118.0	C14—C15—H15B	121.9
C19A—C20A—H20A	118.0	C10—C15—H15B	121.9
C3A—C2A—C1A	118.3 (3)	C12—C13—C14	122.2 (4)
C3A—C2A—H2AB	120.9	C12—C13—H13A	118.9
C1A—C2A—H2AB	120.9	C14—C13—H13A	118.9
C34—C12A—C11A	117.1 (3)	C19—C20—N4	124.0 (5)
C34—C12A—H12A	121.4	C19—C20—H20B	118.0
C11A—C12A—H12A	121.4	N4—C20—H20B	118.0
C15A—C14A—C34	122.1 (3)	C15—C14—C13	121.7 (4)
C15A—C14A—H14A	119.0	C15—C14—H14B	119.1
C34—C14A—H14A	119.0	C13—C14—H14B	119.1
C12A—C34—C14A	122.2 (3)	C20—C19—C18	119.0 (5)
C12A—C34—H34A	118.9	C20—C19—H19B	120.5
C14A—C34—H34A	118.9	C18—C19—H19B	120.5

C8A—O2A—C16A—O3A	−7.0 (3)	C1—C6—C5—C4	0.7 (4)
C8A—O2A—C16A—C17A	172.41 (19)	C7—C6—C5—C4	−177.9 (2)
C10A—N1A—N2A—N3A	0.2 (3)	C16—O2—C8—C9	−173.9 (2)
C9A—N1A—N2A—N3A	−176.9 (2)	C16—O2—C8—C7	67.8 (3)
C16A—O2A—C8A—C9A	−173.48 (19)	C8—O2—C16—O3	1.9 (4)
C16A—O2A—C8A—C7A	67.0 (3)	C8—O2—C16—C17	−179.1 (2)
N1A—N2A—N3A—C11A	−0.2 (3)	C5—C6—C1—C2	−0.4 (4)
C10A—C11A—N3A—N2A	0.1 (3)	C7—C6—C1—C2	178.3 (2)
C12A—C11A—N3A—N2A	−178.9 (3)	C1—C6—C7—O1	−1.8 (4)
O3A—C16A—C17A—C18A	166.8 (2)	C5—C6—C7—O1	176.8 (2)
O2A—C16A—C17A—C18A	−12.6 (3)	C1—C6—C7—C8	−179.7 (2)
O3A—C16A—C17A—C21A	−10.7 (4)	C5—C6—C7—C8	−1.1 (4)
O2A—C16A—C17A—C21A	169.9 (2)	O2—C8—C7—O1	20.1 (3)
O2A—C8A—C7A—O1A	25.2 (3)	C9—C8—C7—O1	−94.7 (3)
C9A—C8A—C7A—O1A	−92.5 (3)	O2—C8—C7—C6	−162.0 (2)
O2A—C8A—C7A—C6A	−156.8 (2)	C9—C8—C7—C6	83.3 (3)
C9A—C8A—C7A—C6A	85.5 (3)	C10—N1—N2—N3	0.3 (3)
C21A—C17A—C18A—C19A	−0.1 (4)	C9—N1—N2—N3	−177.7 (2)
C16A—C17A—C18A—C19A	−177.5 (2)	C10—N1—C9—C8	−99.2 (3)
N2A—N1A—C10A—C11A	−0.2 (3)	N2—N1—C9—C8	78.4 (3)
C9A—N1A—C10A—C11A	176.6 (2)	O2—C8—C9—N1	53.2 (3)
N2A—N1A—C10A—C15A	178.4 (3)	C7—C8—C9—N1	170.8 (2)
C9A—N1A—C10A—C15A	−4.8 (5)	F1—C3—C4—C5	179.7 (2)
N3A—C11A—C10A—N1A	0.0 (3)	C2—C3—C4—C5	−0.3 (4)
C12A—C11A—C10A—N1A	179.2 (2)	C6—C5—C4—C3	−0.4 (4)
N3A—C11A—C10A—C15A	−178.7 (2)	N2—N1—C10—C11	−0.3 (3)
C12A—C11A—C10A—C15A	0.4 (4)	C9—N1—C10—C11	177.5 (2)
C4A—C5A—C6A—C1A	−0.9 (4)	N2—N1—C10—C15	179.2 (3)
C4A—C5A—C6A—C7A	177.8 (3)	C9—N1—C10—C15	−3.0 (5)
O1A—C7A—C6A—C5A	−176.1 (3)	O3—C16—C17—C18	−176.7 (3)
C8A—C7A—C6A—C5A	6.0 (4)	O2—C16—C17—C18	4.4 (4)
O1A—C7A—C6A—C1A	2.6 (4)	O3—C16—C17—C21	3.0 (4)
C8A—C7A—C6A—C1A	−175.3 (2)	O2—C16—C17—C21	−175.9 (3)
C10A—N1A—C9A—C8A	−94.4 (3)	F1—C3—C2—C1	−179.4 (2)
N2A—N1A—C9A—C8A	82.2 (3)	C4—C3—C2—C1	0.6 (4)
O2A—C8A—C9A—N1A	74.7 (3)	C6—C1—C2—C3	−0.2 (4)
C7A—C8A—C9A—N1A	−164.2 (2)	N1—N2—N3—C11	−0.2 (3)
C6A—C5A—C4A—C3A	0.3 (5)	N2—N3—C11—C10	0.0 (3)
C18A—C17A—C21A—N4A	1.3 (4)	N2—N3—C11—C12	−179.4 (3)
C16A—C17A—C21A—N4A	178.9 (3)	N1—C10—C11—N3	0.2 (3)
C5A—C6A—C1A—C2A	1.0 (4)	C15—C10—C11—N3	−179.4 (3)
C7A—C6A—C1A—C2A	−177.8 (3)	N1—C10—C11—C12	179.7 (3)
C17A—C21A—N4A—C20A	−1.0 (5)	C15—C10—C11—C12	0.1 (4)
C5A—C4A—C3A—F1A	−178.5 (3)	C21—C17—C18—C19	0.1 (6)
C5A—C4A—C3A—C2A	0.3 (5)	C16—C17—C18—C19	179.8 (4)
C17A—C18A—C19A—C20A	−1.3 (4)	C18—C17—C21—N4	−0.6 (5)
N1A—C10A—C15A—C14A	−178.7 (3)	C16—C17—C21—N4	179.7 (3)
C11A—C10A—C15A—C14A	−0.4 (4)	N3—C11—C12—C13	−179.9 (4)
C21A—N4A—C20A—C19A	−0.5 (5)	C10—C11—C12—C13	0.8 (5)
C18A—C19A—C20A—N4A	1.6 (5)	C17—C21—N4—C20	−0.7 (6)
F1A—C3A—C2A—C1A	178.6 (3)	N1—C10—C15—C14	−179.9 (3)
C4A—C3A—C2A—C1A	−0.2 (5)	C11—C10—C15—C14	−0.4 (5)
C6A—C1A—C2A—C3A	−0.4 (5)	C11—C12—C13—C14	−1.2 (6)
N3A—C11A—C12A—C34	178.5 (3)	C21—N4—C20—C19	2.7 (8)
C10A—C11A—C12A—C34	−0.4 (4)	C10—C15—C14—C13	0.0 (6)
C10A—C15A—C14A—C34	0.4 (4)	C12—C13—C14—C15	0.9 (7)
C11A—C12A—C34—C14A	0.4 (5)	N4—C20—C19—C18	−3.2 (9)
C15A—C14A—C34—C12A	−0.4 (5)	C17—C18—C19—C20	1.7 (7)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1A···Cg2	0.93	2.84	3.654 (2)	147
C8A—H8AA···O1	0.98	2.52	3.499 (3)	177
C5A—H5AA···O1	0.93	2.58	3.350 (4)	140
C9A—H9AA···N2Aⁱ	0.97	2.59	3.483 (4)	153
C2A—H2AB···O3ⁱⁱ	0.93	2.55	3.374 (4)	148
C9—H9A···O3A	0.97	2.58	2.992 (3)	106
C9—H9B···O3A	0.97	2.55	2.992 (3)	108
C18—H18B···O2	0.93	2.40	2.734 (5)	101
C20—H20B···N2ⁱⁱⁱ	0.93	2.62	3.545 (7)	174
C21A—H21A···O3A	0.93	2.49	2.812 (4)	100

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

Experimental details

Crystal data
Chemical formula	C₂₁H₁₅FN₄O₃
M_r	390.37
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	10.6707 (10), 10.762 (1), 17.2223 (17)
α, β, γ (°)	81.199 (2), 72.270 (2), 81.439 (2)
V (Å³)	1850.6 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.30 × 0.23 × 0.09

Data collection
Diffractometer	Siemens SMART 1000 CCD area detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.970, 0.991
No. of measured, independent and observed [I > 2σ(I)] reflections	10479, 7131, 4047
R_int	0.023
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.057, 0.143, 1.00
No. of reflections	7131
No. of parameters	523
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.19, −0.17

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 1997a), SHELXL97 (Sheldrick, 1997a), SHELXTL (Sheldrick, 1997b), SHELXTL, 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
C1—H1A···Cg2	0.93	2.838	3.654 (2)	147.21
C8A—H8AA···O1	0.98	2.520	3.499 (3)	177.12
C5A—H5AA···O1	0.93	2.582	3.350 (4)	140.20
C9A—H9AA···N2Aⁱ	0.97	2.592	3.483 (4)	152.67
C2A—H2AB···O3ⁱⁱ	0.93	2.547	3.374 (4)	148.15
C9—H9A···O3A	0.97	2.577	2.992 (3)	105.96
C9—H9B···O3A	0.97	2.553	2.992 (3)	107.56
C18—H18B···O2	0.93	2.404	2.734 (5)	100.66
C20—H20B···N2ⁱⁱⁱ	0.93	2.618	3.545 (7)	174.22
C21A—H21A···O3A	0.93	2.492	2.812 (4)	100.35

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

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