4-(4-Fluoro­anilino)-N-(4-fluoro­phen­yl)-3-nitro­benzamide

Wang, Y.; Fan, K.; Li, C.; Ge, C.

doi:10.1107/S1600536810040687

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 66| Part 11| November 2010| Page o2909

https://doi.org/10.1107/S1600536810040687

Open

access

4-(4-Fluoroanilino)-N-(4-fluorophenyl)-3-nitrobenzamide

Yong Wang,^a ^* Kaiqing Fan,^b Chenghong Li ^a and Changhua Ge ^a

^aSchool of Pharmaceutical and Chemical Engineering, Taizhou University, Linhai 317000, People's Republic of China, and ^bAgronomy Department, Jiangsu Polytechnic College of Agriculture and Forestry, Jurong 212400 Jiangsu, People's Republic of China
^*Correspondence e-mail: yutaitang@hotmail.com

(Received 16 September 2010; accepted 11 October 2010; online 23 October 2010)

In the title compound, C₁₉H₁₃F₂N₃O₃, the anilinobenzamide unit is essentially planar, with a maximum deviation of 0.036 (3) Å. The nitro group and the benzene ring form dihedral angles of 9.6 (5)and 62.20 (8)°, respectively, with the anilinobenzamide unit. An intramolecular N—H⋯O interaction occurs. In the crystal, molecules are linked by weak intermolecular C—H⋯O, N—H⋯O and C—H⋯F hydrogen bonds, which stabilize the structure.

Related literature

For comparison of bond lengths, see: Allen et al. (1987 ). For the synthetic procedure, see: Schelz & Inst (1978 ).

Experimental

Crystal data

C₁₉H₁₃F₂N₃O₃
M_r = 369.32
Triclinic, $[P \overline 1]$
a = 7.8510 (16) Å
b = 8.2720 (17) Å
c = 13.835 (3) Å
α = 74.75 (3)°
β = 85.67 (3)°
γ = 70.76 (3)°
V = 818.4 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.12 mm⁻¹
T = 293 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 = 0.965, T_max = 0.988
3198 measured reflections
2962 independent reflections
1559 reflections with I > 2σ(I)
R_int = 0.026
3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F² > 2σ(F²)] = 0.058
wR(F²) = 0.155
S = 1.00
2962 reflections
245 parameters
H-atom parameters constrained
Δρ_max = 0.16 e Å⁻³
Δρ_min = −0.18 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O3ⁱ	0.86	2.37	3.185 (4)	158
N2—H2A⋯O2	0.86	1.98	2.636 (4)	132
C2—H2B⋯O3ⁱ	0.93	2.40	3.240 (5)	151
C10—H10A⋯F1ⁱⁱ	0.93	2.53	3.205 (4)	130
C15—H15A⋯O1ⁱⁱⁱ	0.93	2.55	3.454 (4)	164
C16—H16A⋯F2^iv	0.93	2.39	3.272 (5)	158
Symmetry codes: (i) x, y-1, z; (ii) -x+1, -y, -z; (iii) -x+1, -y, -z+1; (iv) -x+1, -y-1, -z+1.

Data collection: CAD-4 Software (Enraf–Nonius, 1994); 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: PLATON (Spek, 2009 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536810040687/pv2329sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810040687/pv2329Isup2.hkl

checkCIF report

Comment top

The crystal structure of the title compound, (I), is presented in this article. In the title molecule (Fig. 1), the bond lengths and angles are within normal ranges (Allen et al., 1987). The phenylaminobenzamide moiety (C1–C13/N1/O1) is essentially planar with maximum deviation of any atom being 0.036 (3) Å for C11 with F2 lying 0.109 (4) Å out of its plane, nitro group (N3/O2/O3) titlted at an angle 9.6 (5)° from its plane and the phenyl ring (C14–C19) inclined at 62.20 (8)° with its plane. In the crystal structure, weak intermolecular C—H···O, N—H···O and C—H···F hydrogen bonds (Table 1) link the molecules (Fig. 2), in which they may be effective in stabilizing the structure.

Related literature top

For comparison of bond lengths, see: Allen et al. (1987). For the synthetic procedure, see: Schelz & Inst (1978).

Experimental top

4-Chloro-3-nitrobenzamide (4.0 g, 0.02 mol) was heated in 4-fluorobenzenamine (10 ml) for 18 h at 403 K. On completion of the reaction (TLC control) was added ethanol (50 ml), at room temperature. The red precipitate thus formed was filtered, washed with cold ethanol (2 × 15 ml), dried over sodium sulfate to provide 5.8 g (79%) of (I) (Schelz & Inst, 1978). The compound (I) was purified by crystallizing from methanol. The crystals of (I) suitable for X-ray diffraction were obstained by slow evaporation of a methanol solution.

Structure description top

For comparison of bond lengths, see: Allen et al. (1987). For the synthetic procedure, see: Schelz & Inst (1978).

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1994); cell refinement: CAD-4 Software (Enraf–Nonius, 1994); 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: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

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

4-(4-Fluoroanilino)-N-(4-fluorophenyl)-3-nitrobenzamide top

Crystal data top

C₁₉H₁₃F₂N₃O₃	Z = 2
M_r = 369.32	F(000) = 380
Triclinic, P1	D_x = 1.499 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.8510 (16) Å	Cell parameters from 25 reflections
b = 8.2720 (17) Å	θ = 9–12°
c = 13.835 (3) Å	µ = 0.12 mm⁻¹
α = 74.75 (3)°	T = 293 K
β = 85.67 (3)°	Block, colourless
γ = 70.76 (3)°	0.30 × 0.20 × 0.10 mm
V = 818.4 (3) Å³

Data collection top

Enraf–Nonius CAD-4 diffractometer	1559 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.026
Graphite monochromator	θ_max = 25.3°, θ_min = 1.5°
ω and 2θ scans	h = 0→9
Absorption correction: ψ scan (North et al., 1968)	k = −9→9
T_min = 0.965, T_max = 0.988	l = −16→16
3198 measured reflections	3 standard reflections every 200 reflections
2962 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)] = 0.058	H-atom parameters constrained
wR(F²) = 0.155	w = 1/[σ²(F_o²) + (0.065P)²] where P = (F_o² + 2F_c²)/3
S = 1.00	(Δ/σ)_max < 0.001
2962 reflections	Δρ_max = 0.16 e Å⁻³
245 parameters	Δρ_min = −0.18 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: 0.021 (4)

Crystal data top

C₁₉H₁₃F₂N₃O₃	γ = 70.76 (3)°
M_r = 369.32	V = 818.4 (3) Å³
Triclinic, P1	Z = 2
a = 7.8510 (16) Å	Mo Kα radiation
b = 8.2720 (17) Å	µ = 0.12 mm⁻¹
c = 13.835 (3) Å	T = 293 K
α = 74.75 (3)°	0.30 × 0.20 × 0.10 mm
β = 85.67 (3)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	1559 reflections with I > 2σ(I)
Absorption correction: ψ scan (North et al., 1968)	R_int = 0.026
T_min = 0.965, T_max = 0.988	3 standard reflections every 200 reflections
3198 measured reflections	intensity decay: 1%
2962 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.058	0 restraints
wR(F²) = 0.155	H-atom parameters constrained
S = 1.00	Δρ_max = 0.16 e Å⁻³
2962 reflections	Δρ_min = −0.18 e Å⁻³
245 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	0.7511 (3)	0.0655 (3)	−0.12706 (14)	0.0823 (8)
N1	0.1978 (4)	−0.2157 (3)	0.58538 (17)	0.0468 (7)
H1A	0.2383	−0.2652	0.5372	0.056*
F2	−0.0468 (3)	−0.6359 (3)	0.90592 (15)	0.0839 (8)
C1	0.0848 (6)	−0.5958 (5)	0.7467 (3)	0.0687 (12)
H1C	0.0888	−0.7083	0.7443	0.082*
N2	0.4401 (4)	0.3033 (3)	0.20096 (18)	0.0511 (8)
H2A	0.4232	0.4141	0.1934	0.061*
O1	0.1462 (4)	0.0382 (3)	0.63333 (16)	0.0645 (8)
C2	0.1458 (5)	−0.4877 (4)	0.6679 (3)	0.0618 (11)
H2B	0.1932	−0.5290	0.6120	0.074*
O2	0.3708 (4)	0.5620 (3)	0.29073 (19)	0.0787 (9)
C3	0.1378 (4)	−0.3197 (4)	0.6703 (2)	0.0424 (8)
N3	0.3373 (4)	0.4670 (4)	0.3685 (2)	0.0579 (9)
C4	0.0683 (5)	−0.2610 (5)	0.7541 (2)	0.0515 (9)
H4A	0.0612	−0.1478	0.7569	0.062*
O3	0.3066 (5)	0.5176 (4)	0.4448 (2)	0.1081 (13)
C5	0.0093 (5)	−0.3689 (5)	0.8339 (2)	0.0573 (10)
H5A	−0.0360	−0.3301	0.8909	0.069*
C6	0.0189 (5)	−0.5329 (5)	0.8276 (3)	0.0577 (10)
C7	0.1996 (4)	−0.0465 (4)	0.5702 (2)	0.0413 (8)
C8	0.2697 (4)	0.0325 (4)	0.4724 (2)	0.0367 (7)
C9	0.3296 (4)	−0.0471 (4)	0.3930 (2)	0.0458 (9)
H9A	0.3288	−0.1616	0.3996	0.055*
C10	0.3893 (4)	0.0400 (4)	0.3058 (2)	0.0463 (9)
H10A	0.4292	−0.0178	0.2550	0.056*
C11	0.3924 (4)	0.2150 (4)	0.2904 (2)	0.0408 (8)
C12	0.3347 (4)	0.2909 (4)	0.3723 (2)	0.0411 (8)
C13	0.2751 (4)	0.2014 (4)	0.4597 (2)	0.0417 (8)
H13A	0.2376	0.2568	0.5116	0.050*
C14	0.5150 (5)	0.2322 (4)	0.1184 (2)	0.0422 (8)
C15	0.6711 (5)	0.0901 (5)	0.1283 (2)	0.0518 (9)
H15A	0.7234	0.0318	0.1914	0.062*
C16	0.7504 (5)	0.0333 (5)	0.0459 (3)	0.0574 (10)
H16A	0.8563	−0.0623	0.0524	0.069*
C17	0.6702 (6)	0.1204 (5)	−0.0458 (3)	0.0554 (10)
C18	0.5142 (5)	0.2600 (5)	−0.0589 (2)	0.0566 (10)
H18A	0.4617	0.3155	−0.1221	0.068*
C19	0.4358 (5)	0.3171 (4)	0.0244 (2)	0.0495 (9)
H19A	0.3298	0.4126	0.0173	0.059*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
F1	0.114 (2)	0.0861 (17)	0.0570 (13)	−0.0353 (15)	0.0258 (13)	−0.0374 (12)
N1	0.065 (2)	0.0442 (16)	0.0382 (15)	−0.0275 (15)	0.0133 (13)	−0.0135 (12)
F2	0.108 (2)	0.0535 (14)	0.0715 (14)	−0.0251 (13)	0.0345 (13)	0.0043 (11)
C1	0.094 (3)	0.038 (2)	0.068 (3)	−0.020 (2)	0.017 (2)	−0.0092 (19)
N2	0.078 (2)	0.0423 (16)	0.0389 (16)	−0.0291 (16)	0.0172 (15)	−0.0130 (13)
O1	0.104 (2)	0.0492 (15)	0.0487 (14)	−0.0345 (15)	0.0227 (14)	−0.0192 (12)
C2	0.090 (3)	0.044 (2)	0.050 (2)	−0.024 (2)	0.020 (2)	−0.0121 (17)
O2	0.136 (3)	0.0554 (16)	0.0587 (16)	−0.0535 (17)	0.0343 (16)	−0.0184 (13)
C3	0.052 (2)	0.042 (2)	0.0342 (18)	−0.0201 (17)	0.0066 (16)	−0.0069 (15)
N3	0.089 (3)	0.0494 (18)	0.0465 (18)	−0.0370 (18)	0.0176 (17)	−0.0165 (16)
C4	0.063 (3)	0.055 (2)	0.044 (2)	−0.031 (2)	0.0094 (18)	−0.0129 (17)
O3	0.225 (4)	0.072 (2)	0.0626 (18)	−0.087 (2)	0.050 (2)	−0.0403 (16)
C5	0.068 (3)	0.064 (3)	0.043 (2)	−0.028 (2)	0.0144 (18)	−0.0145 (18)
C6	0.062 (3)	0.046 (2)	0.049 (2)	−0.0125 (19)	0.0141 (18)	0.0043 (17)
C7	0.045 (2)	0.0400 (19)	0.0396 (18)	−0.0162 (17)	0.0017 (16)	−0.0091 (16)
C8	0.040 (2)	0.0355 (18)	0.0351 (17)	−0.0139 (15)	−0.0003 (14)	−0.0072 (14)
C9	0.061 (2)	0.043 (2)	0.0426 (19)	−0.0269 (18)	0.0063 (17)	−0.0134 (15)
C10	0.060 (2)	0.046 (2)	0.0427 (19)	−0.0260 (18)	0.0105 (17)	−0.0201 (16)
C11	0.044 (2)	0.0385 (19)	0.0412 (19)	−0.0149 (16)	0.0005 (15)	−0.0106 (15)
C12	0.053 (2)	0.0365 (18)	0.0384 (18)	−0.0195 (17)	0.0029 (16)	−0.0110 (15)
C13	0.053 (2)	0.0418 (19)	0.0339 (17)	−0.0186 (17)	0.0030 (15)	−0.0116 (14)
C14	0.060 (2)	0.0416 (19)	0.0353 (18)	−0.0296 (19)	0.0097 (16)	−0.0125 (15)
C15	0.062 (3)	0.050 (2)	0.043 (2)	−0.020 (2)	0.0041 (18)	−0.0094 (16)
C16	0.064 (3)	0.049 (2)	0.060 (2)	−0.0173 (19)	0.014 (2)	−0.0197 (19)
C17	0.082 (3)	0.060 (2)	0.041 (2)	−0.040 (2)	0.022 (2)	−0.0237 (18)
C18	0.073 (3)	0.065 (3)	0.039 (2)	−0.036 (2)	0.0023 (19)	−0.0083 (18)
C19	0.050 (2)	0.046 (2)	0.049 (2)	−0.0173 (18)	0.0048 (18)	−0.0066 (17)

Geometric parameters (Å, º) top

F1—C17	1.358 (3)	C5—H5A	0.9300
N1—C7	1.365 (4)	C7—C8	1.490 (4)
N1—C3	1.413 (3)	C8—C13	1.376 (4)
N1—H1A	0.8600	C8—C9	1.400 (4)
F2—C6	1.373 (4)	C9—C10	1.369 (4)
C1—C6	1.354 (5)	C9—H9A	0.9300
C1—C2	1.382 (4)	C10—C11	1.415 (4)
C1—H1C	0.9300	C10—H10A	0.9300
N2—C11	1.357 (4)	C11—C12	1.412 (4)
N2—C14	1.421 (4)	C12—C13	1.378 (4)
N2—H2A	0.8600	C13—H13A	0.9300
O1—C7	1.225 (3)	C14—C15	1.376 (4)
C2—C3	1.379 (4)	C14—C19	1.388 (4)
C2—H2B	0.9300	C15—C16	1.375 (4)
O2—N3	1.222 (3)	C15—H15A	0.9300
C3—C4	1.380 (4)	C16—C17	1.366 (5)
N3—O3	1.214 (3)	C16—H16A	0.9300
N3—C12	1.451 (4)	C17—C18	1.363 (5)
C4—C5	1.381 (4)	C18—C19	1.384 (4)
C4—H4A	0.9300	C18—H18A	0.9300
C5—C6	1.360 (5)	C19—H19A	0.9300

C7—N1—C3	128.1 (3)	C10—C9—C8	121.5 (3)
C7—N1—H1A	115.9	C10—C9—H9A	119.3
C3—N1—H1A	115.9	C8—C9—H9A	119.3
C6—C1—C2	117.9 (4)	C9—C10—C11	122.1 (3)
C6—C1—H1C	121.0	C9—C10—H10A	118.9
C2—C1—H1C	121.0	C11—C10—H10A	118.9
C11—N2—C14	126.9 (3)	N2—C11—C12	123.5 (3)
C11—N2—H2A	116.6	N2—C11—C10	121.2 (3)
C14—N2—H2A	116.6	C12—C11—C10	115.2 (3)
C3—C2—C1	121.4 (3)	C13—C12—C11	121.9 (3)
C3—C2—H2B	119.3	C13—C12—N3	116.8 (3)
C1—C2—H2B	119.3	C11—C12—N3	121.2 (3)
C2—C3—C4	118.6 (3)	C8—C13—C12	121.9 (3)
C2—C3—N1	117.8 (3)	C8—C13—H13A	119.0
C4—C3—N1	123.6 (3)	C12—C13—H13A	119.0
O3—N3—O2	120.7 (3)	C15—C14—C19	119.5 (3)
O3—N3—C12	118.4 (3)	C15—C14—N2	121.5 (3)
O2—N3—C12	120.9 (3)	C19—C14—N2	118.8 (3)
C3—C4—C5	120.5 (3)	C16—C15—C14	120.6 (3)
C3—C4—H4A	119.7	C16—C15—H15A	119.7
C5—C4—H4A	119.7	C14—C15—H15A	119.7
C6—C5—C4	118.7 (3)	C17—C16—C15	118.5 (4)
C6—C5—H5A	120.7	C17—C16—H16A	120.7
C4—C5—H5A	120.7	C15—C16—H16A	120.7
C1—C6—C5	122.9 (3)	F1—C17—C18	119.1 (3)
C1—C6—F2	119.1 (3)	F1—C17—C16	118.1 (4)
C5—C6—F2	117.9 (3)	C18—C17—C16	122.8 (3)
O1—C7—N1	122.2 (3)	C17—C18—C19	118.3 (3)
O1—C7—C8	120.9 (3)	C17—C18—H18A	120.8
N1—C7—C8	116.9 (3)	C19—C18—H18A	120.8
C13—C8—C9	117.3 (3)	C18—C19—C14	120.2 (3)
C13—C8—C7	115.9 (3)	C18—C19—H19A	119.9
C9—C8—C7	126.8 (3)	C14—C19—H19A	119.9

C6—C1—C2—C3	−0.9 (6)	N2—C11—C12—C13	175.3 (3)
C1—C2—C3—C4	0.5 (6)	C10—C11—C12—C13	−1.7 (5)
C1—C2—C3—N1	−178.1 (3)	N2—C11—C12—N3	−5.3 (5)
C7—N1—C3—C2	178.7 (3)	C10—C11—C12—N3	177.6 (3)
C7—N1—C3—C4	0.2 (5)	O3—N3—C12—C13	7.8 (5)
C2—C3—C4—C5	0.4 (5)	O2—N3—C12—C13	−172.6 (3)
N1—C3—C4—C5	178.9 (3)	O3—N3—C12—C11	−171.5 (4)
C3—C4—C5—C6	−0.9 (5)	O2—N3—C12—C11	8.1 (5)
C2—C1—C6—C5	0.5 (6)	C9—C8—C13—C12	0.8 (5)
C2—C1—C6—F2	178.4 (3)	C7—C8—C13—C12	−179.1 (3)
C4—C5—C6—C1	0.4 (6)	C11—C12—C13—C8	0.4 (5)
C4—C5—C6—F2	−177.5 (3)	N3—C12—C13—C8	−178.9 (3)
C3—N1—C7—O1	0.3 (5)	C11—N2—C14—C15	−56.2 (5)
C3—N1—C7—C8	−179.6 (3)	C11—N2—C14—C19	128.7 (3)
O1—C7—C8—C13	1.9 (5)	C19—C14—C15—C16	1.0 (5)
N1—C7—C8—C13	−178.2 (3)	N2—C14—C15—C16	−174.0 (3)
O1—C7—C8—C9	−178.0 (3)	C14—C15—C16—C17	−0.4 (5)
N1—C7—C8—C9	1.9 (5)	C15—C16—C17—F1	178.9 (3)
C13—C8—C9—C10	−0.7 (5)	C15—C16—C17—C18	−0.6 (5)
C7—C8—C9—C10	179.2 (3)	F1—C17—C18—C19	−178.4 (3)
C8—C9—C10—C11	−0.6 (5)	C16—C17—C18—C19	1.0 (5)
C14—N2—C11—C12	173.7 (3)	C17—C18—C19—C14	−0.4 (5)
C14—N2—C11—C10	−9.4 (5)	C15—C14—C19—C18	−0.5 (5)
C9—C10—C11—N2	−175.3 (3)	N2—C14—C19—C18	174.6 (3)
C9—C10—C11—C12	1.8 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O3ⁱ	0.86	2.37	3.185 (4)	158
N2—H2A···O2	0.86	1.98	2.636 (4)	132
N2—H2A···N3	0.86	2.58	2.917 (4)	105
C2—H2B···O3ⁱ	0.93	2.40	3.240 (5)	151
C4—H4A···O1	0.93	2.20	2.821 (4)	123
C10—H10A···F1ⁱⁱ	0.93	2.53	3.205 (4)	130
C13—H13A···O1	0.93	2.39	2.728 (4)	102
C13—H13A···O3	0.93	2.33	2.661 (5)	100
C15—H15A···O1ⁱⁱⁱ	0.93	2.55	3.454 (4)	164
C16—H16A···F2^iv	0.93	2.39	3.272 (5)	158

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

Experimental details

Crystal data
Chemical formula	C₁₉H₁₃F₂N₃O₃
M_r	369.32
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	7.8510 (16), 8.2720 (17), 13.835 (3)
α, β, γ (°)	74.75 (3), 85.67 (3), 70.76 (3)
V (Å³)	818.4 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.12
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	0.965, 0.988
No. of measured, independent and observed [I > 2σ(I)] reflections	3198, 2962, 1559
R_int	0.026
(sin θ/λ)_max (Å⁻¹)	0.601

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.058, 0.155, 1.00
No. of reflections	2962
No. of parameters	245
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.16, −0.18

Computer programs: CAD-4 Software (Enraf–Nonius, 1994), XCAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O3ⁱ	0.86	2.37	3.185 (4)	158
N2—H2A···O2	0.86	1.98	2.636 (4)	132
C2—H2B···O3ⁱ	0.93	2.40	3.240 (5)	151
C10—H10A···F1ⁱⁱ	0.93	2.53	3.205 (4)	130
C15—H15A···O1ⁱⁱⁱ	0.93	2.55	3.454 (4)	164
C16—H16A···F2^iv	0.93	2.39	3.272 (5)	158

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

Acknowledgements

The authors thank Dr Shan Liu of Nanjing University of Technology for useful discussions and the Center of Testing and Analysis, Nanjing University, for support.

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 (1994). 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
Schelz, D. & Inst, F. (1978). Helv. Chim. Acta, 61, 2452–2462. CrossRef CAS Web of Science Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar