2-Amino-4-(4-fluoro­phen­yl)-6-(naphthalen-1-yl)pyridine-3-carbonitrile

Wang, J.-Q.; Tang, S.-G.; Guo, C.

doi:10.1107/S1600536810050804

organic compounds

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Volume 67| Part 1| January 2011| Page o56

https://doi.org/10.1107/S1600536810050804

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2-Amino-4-(4-fluorophenyl)-6-(naphthalen-1-yl)pyridine-3-carbonitrile

Jian-Qiang Wang,^a Shi-Gui Tang ^b and Cheng Guo ^a ^*

^aCollege of Science, Nanjing University of Technology, Nanjing 210009, People's Republic of China, and ^bBiotechnology and Pharmaceutical Engineering, Nanjing University of Technology, Nanjing 210009, People's Republic of China
^*Correspondence e-mail: guocheng@njut.edu.cn

(Received 21 November 2010; accepted 3 December 2010; online 8 December 2010)

The title compound, C₂₂H₁₄FN₃, was prepared by a one-pot condensation using malononitrile, an aromatic aldehyde, a methyl ketone and ammonium acetate as reactants under microwave irradiation. The pyridine ring is twisted with respect to the benzene ring and the naphthalene ring system, making dihedral angles of 41.9 (1) and 45.2 (1)°, respectively. In the crystal, molecules are connected via intermolecular N—H⋯N and C—H⋯F hydrogen bonds, forming a three-dimensional network.

Related literature

For the use of 2-amino-3-cyanopyridines as intermediates in the preparation of heterocyclic compounds, see: Shishoo et al. (1983 ). For bond-length data, see: Allen et al. (1987 ).

Experimental

Crystal data

C₂₂H₁₄FN₃
M_r = 339.36
Monoclinic, P 2₁ /c
a = 14.531 (3) Å
b = 8.0900 (16) Å
c = 15.516 (3) Å
β = 110.04 (3)°
V = 1713.6 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 292 K
0.30 × 0.20 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: ψ scan (North et al., 1968 ) T_min = 0.974, T_max = 0.991
3274 measured reflections
3144 independent reflections
2046 reflections with I > 2σ(I)
R_int = 0.056
3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F² > 2σ(F²)] = 0.062
wR(F²) = 0.177
S = 1.00
3144 reflections
236 parameters
H-atom parameters constrained
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.29 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯N1ⁱ	0.86	2.33	3.149 (3)	158
C20—H20A⋯Fⁱⁱ	0.93	2.50	3.284 (4)	142
Symmetry codes: (i) -x+2, -y+1, -z; (ii) $[x+1, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: CAD-4 Software (Enraf–Nonius, 1985 ); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo,1995 ); 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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536810050804/vm2063sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810050804/vm2063Isup2.hkl

checkCIF report

Comment top

Derivatives of 2-amino-3-cyanopyridine are important and useful intermediates in preparing a varity of heterocyclic compounds (Shishoo et al., 1983). Therefore, the synthesis of 2-amino-3-cyanopyridine derivatives attracts much interest in organic chemistry. Here, the single-crystal structure of the title compound (I), C₂₂H₁₄FN₃, is reported.

The title compound (Fig. 1) consists of a pyridine ring bearing a 4-fluoro phenyl at C7, a naphthyl at C10, an amino group at C9, and a cyano group at C8. The pyridine ring is twisted with respect to the benzene ring and naphthalene ring, with dihedral angles of 41.9 (1)° and 45.2 (1)°, respectively. The bond lengths and angles are within the reported values (Allen et al., 1987). Intermolecular N—H···N and C—H···F hydrogen bonds (Table 1, Fig. 2), and C—H···π and π–π stacking interactions help to stabilize the crystal structure.

Related literature top

For the use of 2-amino-3-cyanopyridines as intermediates in the preparation of heterocyclic compounds, see: Shishoo et al. (1983). For bond-length data, see: Allen et al. (1987).

Experimental top

The title compound (I) was prepared from a mixture of 4-fluorobenzaldehyde (2 mmol), malononitrile (2 mmol), 1-naphthaldehyde (2 mmol) and ammonium acetate (16 mmol) under microwave irradiation (6 min, WF-4000M microwave reaction system). After cooling to room temperature, the resulting solid product was filtered off and recrystallized from methanol to give compound (I). Colorless single crystals suitable for X-ray analysis were obtained by dissolving (I) (0.5 g) in methanol (20 ml) and slowly evaporating the solvent at room temperature for a period of about two weeks.

Structure description top

For the use of 2-amino-3-cyanopyridines as intermediates in the preparation of heterocyclic compounds, see: Shishoo et al. (1983). For bond-length data, see: Allen et al. (1987).

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1985); cell refinement: CAD-4 Software (Enraf–Nonius, 1985); data reduction: XCAD4 (Harms & Wocadlo,1995); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of (I), with the atom-numbering scheme and displacement ellipsoids at the 30% probability level.
	Fig. 2. A packing diagram of (I). Intermolecular hydrogen bonds are shown as dashed lines.

2-Amino-4-(4-fluorophenyl)-6-(naphthalen-1-yl)pyridine-3-carbonitrile top

Crystal data top

C₂₂H₁₄FN₃	F(000) = 704
M_r = 339.36	D_x = 1.315 Mg m⁻³
Monoclinic, P2₁/c	Melting point: 422.15 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 14.531 (3) Å	Cell parameters from 25 reflections
b = 8.0900 (16) Å	θ = 9–13°
c = 15.516 (3) Å	µ = 0.09 mm⁻¹
β = 110.04 (3)°	T = 292 K
V = 1713.6 (6) Å³	Block, colourless
Z = 4	0.30 × 0.20 × 0.10 mm

Data collection top

Enraf–Nonius CAD-4 diffractometer	2046 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.056
Graphite monochromator	θ_max = 25.4°, θ_min = 1.5°
ω/2θ scans	h = 0→17
Absorption correction: ψ scan (North et al., 1968)	k = 0→9
T_min = 0.974, T_max = 0.991	l = −18→17
3274 measured reflections	3 standard reflections every 200 reflections
3144 independent reflections	intensity decay: 1%

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)] = 0.062	H-atom parameters constrained
wR(F²) = 0.177	w = 1/[σ²(F_o²) + (0.1P)² + 0.2P] where P = (F_o² + 2F_c²)/3
S = 1.00	(Δ/σ)_max < 0.001
3144 reflections	Δρ_max = 0.20 e Å⁻³
236 parameters	Δρ_min = −0.29 e Å⁻³
0 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: 0.016 (3)

Crystal data top

C₂₂H₁₄FN₃	V = 1713.6 (6) Å³
M_r = 339.36	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 14.531 (3) Å	µ = 0.09 mm⁻¹
b = 8.0900 (16) Å	T = 292 K
c = 15.516 (3) Å	0.30 × 0.20 × 0.10 mm
β = 110.04 (3)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	2046 reflections with I > 2σ(I)
Absorption correction: ψ scan (North et al., 1968)	R_int = 0.056
T_min = 0.974, T_max = 0.991	3 standard reflections every 200 reflections
3274 measured reflections	intensity decay: 1%
3144 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.062	0 restraints
wR(F²) = 0.177	H-atom parameters constrained
S = 1.00	Δρ_max = 0.20 e Å⁻³
3144 reflections	Δρ_min = −0.29 e Å⁻³
236 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
F	0.33760 (12)	0.1683 (3)	0.00030 (15)	0.1049 (8)
N1	0.91754 (14)	0.3544 (2)	0.03593 (12)	0.0425 (5)
C1	0.5928 (2)	0.2725 (4)	0.0869 (2)	0.0601 (8)
H1B	0.6403	0.3032	0.1419	0.072*
N2	0.87074 (16)	0.4912 (3)	−0.10104 (14)	0.0566 (6)
H2A	0.9316	0.5106	−0.0915	0.068*
H2B	0.8267	0.5267	−0.1502	0.068*
C2	0.4983 (2)	0.2457 (4)	0.0839 (2)	0.0700 (9)
H2C	0.4811	0.2591	0.1360	0.084*
N3	0.6218 (2)	0.4965 (4)	−0.19941 (17)	0.0838 (9)
C3	0.4303 (2)	0.1989 (4)	0.0021 (3)	0.0694 (9)
C4	0.4519 (2)	0.1766 (4)	−0.0751 (2)	0.0673 (9)
H4A	0.4039	0.1422	−0.1291	0.081*
C5	0.54649 (19)	0.2056 (4)	−0.07242 (19)	0.0565 (7)
H5A	0.5622	0.1927	−0.1253	0.068*
C6	0.61841 (18)	0.2543 (3)	0.00910 (17)	0.0485 (6)
C7	0.72116 (18)	0.2857 (3)	0.01511 (16)	0.0450 (6)
C8	0.74512 (17)	0.3731 (3)	−0.05147 (15)	0.0453 (6)
C9	0.84442 (17)	0.4055 (3)	−0.03910 (15)	0.0424 (6)
C10	0.89413 (17)	0.2700 (3)	0.09979 (15)	0.0402 (6)
C11	0.79866 (18)	0.2324 (3)	0.09168 (16)	0.0457 (6)
H11A	0.7861	0.1716	0.1373	0.055*
C12	0.6732 (2)	0.4389 (4)	−0.13286 (18)	0.0550 (7)
C13	0.97766 (17)	0.2280 (3)	0.18524 (15)	0.0404 (6)
C14	1.06861 (17)	0.1664 (3)	0.18259 (15)	0.0412 (6)
C15	1.08360 (19)	0.1133 (3)	0.10156 (17)	0.0491 (6)
H15A	1.0318	0.1182	0.0461	0.059*
C16	1.1715 (2)	0.0555 (4)	0.1025 (2)	0.0650 (8)
H16A	1.1792	0.0200	0.0484	0.078*
C17	1.2509 (2)	0.0492 (4)	0.1853 (2)	0.0746 (9)
H17A	1.3117	0.0130	0.1856	0.090*
C18	1.2395 (2)	0.0954 (4)	0.2644 (2)	0.0667 (8)
H18A	1.2928	0.0899	0.3187	0.080*
C19	1.14842 (18)	0.1521 (3)	0.26713 (17)	0.0479 (6)
C20	1.1338 (2)	0.1915 (4)	0.34944 (17)	0.0582 (8)
H20A	1.1861	0.1836	0.4044	0.070*
C21	1.0458 (2)	0.2407 (4)	0.35084 (17)	0.0586 (8)
H21A	1.0369	0.2618	0.4064	0.070*
C22	0.9674 (2)	0.2599 (3)	0.26778 (17)	0.0504 (7)
H22A	0.9070	0.2952	0.2691	0.060*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
F	0.0381 (10)	0.142 (2)	0.1317 (18)	0.0019 (11)	0.0249 (11)	0.0234 (15)
N1	0.0410 (11)	0.0474 (12)	0.0378 (11)	0.0010 (9)	0.0116 (9)	0.0053 (9)
C1	0.0453 (16)	0.076 (2)	0.0558 (16)	−0.0088 (14)	0.0141 (13)	−0.0064 (15)
N2	0.0474 (12)	0.0720 (16)	0.0473 (12)	0.0008 (11)	0.0124 (10)	0.0190 (11)
C2	0.0548 (19)	0.089 (2)	0.072 (2)	0.0004 (17)	0.0296 (17)	−0.0007 (18)
N3	0.0727 (18)	0.107 (2)	0.0574 (15)	0.0126 (16)	0.0032 (13)	0.0246 (16)
C3	0.0340 (15)	0.081 (2)	0.091 (2)	0.0045 (14)	0.0193 (16)	0.0118 (19)
C4	0.0428 (16)	0.075 (2)	0.068 (2)	−0.0008 (15)	−0.0019 (14)	0.0053 (17)
C5	0.0471 (16)	0.0647 (18)	0.0512 (16)	−0.0013 (13)	0.0084 (13)	0.0002 (13)
C6	0.0408 (14)	0.0529 (16)	0.0486 (15)	−0.0005 (12)	0.0110 (12)	0.0025 (12)
C7	0.0433 (14)	0.0493 (15)	0.0402 (13)	−0.0029 (11)	0.0114 (11)	−0.0021 (11)
C8	0.0432 (14)	0.0498 (15)	0.0389 (13)	0.0013 (11)	0.0089 (11)	0.0012 (11)
C9	0.0451 (14)	0.0452 (14)	0.0361 (12)	0.0005 (11)	0.0129 (11)	0.0042 (11)
C10	0.0427 (14)	0.0390 (13)	0.0375 (12)	0.0005 (11)	0.0122 (11)	0.0017 (10)
C11	0.0453 (14)	0.0523 (15)	0.0393 (13)	−0.0046 (12)	0.0141 (11)	0.0053 (11)
C12	0.0497 (15)	0.0654 (18)	0.0464 (15)	0.0019 (14)	0.0119 (13)	0.0058 (14)
C13	0.0435 (13)	0.0395 (13)	0.0356 (12)	−0.0039 (11)	0.0101 (10)	0.0007 (10)
C14	0.0433 (14)	0.0362 (13)	0.0399 (13)	−0.0049 (11)	0.0088 (11)	0.0025 (11)
C15	0.0506 (15)	0.0503 (15)	0.0460 (14)	0.0005 (12)	0.0162 (12)	0.0008 (12)
C16	0.0658 (19)	0.0667 (19)	0.0694 (19)	0.0075 (16)	0.0320 (16)	−0.0025 (15)
C17	0.0518 (18)	0.079 (2)	0.091 (2)	0.0124 (16)	0.0209 (18)	−0.0018 (19)
C18	0.0486 (17)	0.067 (2)	0.069 (2)	0.0051 (15)	−0.0003 (14)	0.0018 (16)
C19	0.0459 (15)	0.0411 (14)	0.0477 (15)	−0.0033 (12)	0.0044 (11)	0.0028 (11)
C20	0.0617 (18)	0.0585 (17)	0.0378 (14)	−0.0053 (14)	−0.0044 (13)	−0.0006 (12)
C21	0.073 (2)	0.0647 (18)	0.0340 (14)	−0.0004 (15)	0.0122 (13)	−0.0050 (12)
C22	0.0535 (16)	0.0554 (16)	0.0408 (14)	0.0007 (13)	0.0142 (12)	−0.0001 (12)

Geometric parameters (Å, º) top

F—C3	1.360 (3)	C10—C11	1.383 (3)
N1—C10	1.340 (3)	C10—C13	1.498 (3)
N1—C9	1.344 (3)	C11—H11A	0.9300
C1—C2	1.376 (4)	C13—C22	1.364 (3)
C1—C6	1.387 (4)	C13—C14	1.426 (3)
C1—H1B	0.9300	C14—C15	1.414 (3)
N2—C9	1.342 (3)	C14—C19	1.427 (3)
N2—H2A	0.8600	C15—C16	1.356 (4)
N2—H2B	0.8600	C15—H15A	0.9300
C2—C3	1.369 (4)	C16—C17	1.403 (4)
C2—H2C	0.9300	C16—H16A	0.9300
N3—C12	1.145 (3)	C17—C18	1.347 (4)
C3—C4	1.350 (4)	C17—H17A	0.9300
C4—C5	1.381 (4)	C18—C19	1.414 (4)
C4—H4A	0.9300	C18—H18A	0.9300
C5—C6	1.393 (4)	C19—C20	1.401 (4)
C5—H5A	0.9300	C20—C21	1.347 (4)
C6—C7	1.486 (3)	C20—H20A	0.9300
C7—C8	1.391 (3)	C21—C22	1.406 (4)
C7—C11	1.396 (3)	C21—H21A	0.9300
C8—C9	1.413 (3)	C22—H22A	0.9300
C8—C12	1.438 (3)

C10—N1—C9	118.1 (2)	C10—C11—C7	120.1 (2)
C2—C1—C6	121.1 (3)	C10—C11—H11A	120.0
C2—C1—H1B	119.4	C7—C11—H11A	120.0
C6—C1—H1B	119.4	N3—C12—C8	174.6 (3)
C9—N2—H2A	120.0	C22—C13—C14	119.6 (2)
C9—N2—H2B	120.0	C22—C13—C10	118.2 (2)
H2A—N2—H2B	120.0	C14—C13—C10	122.1 (2)
C3—C2—C1	118.0 (3)	C15—C14—C13	123.9 (2)
C3—C2—H2C	121.0	C15—C14—C19	117.9 (2)
C1—C2—H2C	121.0	C13—C14—C19	118.1 (2)
C4—C3—F	119.2 (3)	C16—C15—C14	121.8 (2)
C4—C3—C2	123.2 (3)	C16—C15—H15A	119.1
F—C3—C2	117.6 (3)	C14—C15—H15A	119.1
C3—C4—C5	118.8 (3)	C15—C16—C17	119.9 (3)
C3—C4—H4A	120.6	C15—C16—H16A	120.0
C5—C4—H4A	120.6	C17—C16—H16A	120.0
C4—C5—C6	120.3 (3)	C18—C17—C16	120.3 (3)
C4—C5—H5A	119.9	C18—C17—H17A	119.8
C6—C5—H5A	119.9	C16—C17—H17A	119.8
C1—C6—C5	118.6 (2)	C17—C18—C19	121.7 (3)
C1—C6—C7	119.4 (2)	C17—C18—H18A	119.1
C5—C6—C7	122.0 (2)	C19—C18—H18A	119.1
C8—C7—C11	117.0 (2)	C20—C19—C18	122.4 (2)
C8—C7—C6	122.8 (2)	C20—C19—C14	119.4 (2)
C11—C7—C6	120.1 (2)	C18—C19—C14	118.2 (2)
C7—C8—C9	119.8 (2)	C21—C20—C19	121.6 (2)
C7—C8—C12	123.3 (2)	C21—C20—H20A	119.2
C9—C8—C12	116.9 (2)	C19—C20—H20A	119.2
N2—C9—N1	116.4 (2)	C20—C21—C22	119.6 (2)
N2—C9—C8	121.8 (2)	C20—C21—H21A	120.2
N1—C9—C8	121.9 (2)	C22—C21—H21A	120.2
N1—C10—C11	123.1 (2)	C13—C22—C21	121.7 (3)
N1—C10—C13	115.9 (2)	C13—C22—H22A	119.2
C11—C10—C13	120.9 (2)	C21—C22—H22A	119.2

C6—C1—C2—C3	0.7 (5)	C8—C7—C11—C10	1.3 (4)
C1—C2—C3—C4	0.6 (5)	C6—C7—C11—C10	−176.3 (2)
C1—C2—C3—F	178.2 (3)	N1—C10—C13—C22	131.9 (3)
F—C3—C4—C5	−179.1 (3)	C11—C10—C13—C22	−43.9 (3)
C2—C3—C4—C5	−1.5 (5)	N1—C10—C13—C14	−44.0 (3)
C3—C4—C5—C6	1.1 (5)	C11—C10—C13—C14	140.2 (2)
C2—C1—C6—C5	−1.0 (4)	C22—C13—C14—C15	173.1 (2)
C2—C1—C6—C7	179.5 (3)	C10—C13—C14—C15	−11.0 (4)
C4—C5—C6—C1	0.1 (4)	C22—C13—C14—C19	−4.6 (3)
C4—C5—C6—C7	179.6 (3)	C10—C13—C14—C19	171.2 (2)
C1—C6—C7—C8	−137.1 (3)	C13—C14—C15—C16	−179.9 (2)
C5—C6—C7—C8	43.4 (4)	C19—C14—C15—C16	−2.1 (4)
C1—C6—C7—C11	40.4 (4)	C14—C15—C16—C17	−0.8 (4)
C5—C6—C7—C11	−139.2 (3)	C15—C16—C17—C18	2.1 (5)
C11—C7—C8—C9	−0.7 (4)	C16—C17—C18—C19	−0.3 (5)
C6—C7—C8—C9	176.9 (2)	C17—C18—C19—C20	176.2 (3)
C11—C7—C8—C12	−178.5 (2)	C17—C18—C19—C14	−2.6 (4)
C6—C7—C8—C12	−1.0 (4)	C15—C14—C19—C20	−175.1 (2)
C10—N1—C9—N2	179.3 (2)	C13—C14—C19—C20	2.8 (3)
C10—N1—C9—C8	0.3 (4)	C15—C14—C19—C18	3.8 (4)
C7—C8—C9—N2	−179.1 (2)	C13—C14—C19—C18	−178.3 (2)
C12—C8—C9—N2	−1.1 (4)	C18—C19—C20—C21	−178.0 (3)
C7—C8—C9—N1	−0.2 (4)	C14—C19—C20—C21	0.8 (4)
C12—C8—C9—N1	177.9 (2)	C19—C20—C21—C22	−2.7 (4)
C9—N1—C10—C11	0.5 (4)	C14—C13—C22—C21	2.9 (4)
C9—N1—C10—C13	−175.3 (2)	C10—C13—C22—C21	−173.1 (2)
N1—C10—C11—C7	−1.3 (4)	C20—C21—C22—C13	0.8 (4)
C13—C10—C11—C7	174.2 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15A···N1	0.93	2.50	2.997 (3)	114
N2—H2A···N1ⁱ	0.86	2.33	3.149 (3)	158
C20—H20A···Fⁱⁱ	0.93	2.50	3.284 (4)	142

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

Experimental details

Crystal data
Chemical formula	C₂₂H₁₄FN₃
M_r	339.36
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	292
a, b, c (Å)	14.531 (3), 8.0900 (16), 15.516 (3)
β (°)	110.04 (3)
V (Å³)	1713.6 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.30 × 0.20 × 0.10

Data collection
Diffractometer	Enraf–Nonius CAD-4
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.974, 0.991
No. of measured, independent and observed [I > 2σ(I)] reflections	3274, 3144, 2046
R_int	0.056
(sin θ/λ)_max (Å⁻¹)	0.603

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.062, 0.177, 1.00
No. of reflections	3144
No. of parameters	236
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.20, −0.29

Computer programs: CAD-4 Software (Enraf–Nonius, 1985), XCAD4 (Harms & Wocadlo,1995), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···N1ⁱ	0.86	2.33	3.149 (3)	158
C20—H20A···Fⁱⁱ	0.93	2.50	3.284 (4)	142

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

Acknowledgements

We gratefully acknowledge the financial support from the Youth Foundation of Nanjing University of Technology (39704011) and the Analysis Center of Nanjing University.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CSD CrossRef Web of Science Google Scholar
Enraf–Nonius (1985). CAD-4 Software. Enraf–Nonius, Delft, The Netherlands. Google Scholar
Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany. Google Scholar
North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351–359. CrossRef IUCr Journals Web of Science Google Scholar
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