Phenyl N-(4-fluorophen­yl)carbamate

Yang, Z.; Wang, Z.-X.

doi:10.1107/S1600536809013312

organic compounds

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ISSN: 2056-9890

Volume 65| Part 5| May 2009| Page o1036

doi:10.1107/S1600536809013312

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Phenyl N-(4-fluorophenyl)carbamate

Zhao Yang ^a and Zhi-Xiang Wang ^a ^*

^aDepartment of Pharmaceutical Engineering, China Pharmaceutical University, Tongjiaxiang No. 24 Nanjing, Nanjing 210009, People's Republic of China
^*Correspondence e-mail: yzcpu@163.com

(Received 7 April 2009; accepted 8 April 2009; online 18 April 2009)

The asymmetric unit of the title compound, C₁₃H₁₀FNO₂, contains two crystallographically independent molecules. The aromatic rings are oriented at dihedral angles of 61.77 (3) and 53.94 (3)° in the two molecules. An N—H⋯O hydrogen bond links the molecules. In the crystal structure, intermolecular N—H⋯O hydrogen bonds link the molecules into chains. Weak C—H⋯π interactions are also present.

Related literature

For a related structure, see: Hynes et al. (2008 ). For bond-length data, see: Allen et al. (1987 ).

Experimental

Crystal data

C₁₃H₁₀FNO₂
M_r = 231.22
Triclinic, $[P \overline 1]$
a = 5.8860 (12) Å
b = 7.8540 (16) Å
c = 24.761 (5) Å
α = 96.62 (3)°
β = 92.82 (3)°
γ = 91.19 (3)°
V = 1135.3 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 294 K
0.10 × 0.10 × 0.08 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: ψ scan (North et al., 1968 ) T_min = 0.990, T_max = 0.992
4548 measured reflections
4110 independent reflections
1662 reflections with I > 2σ(I)
R_int = 0.060
3 standard reflections frequency: 120 min intensity decay: 1%

Refinement

R[F² > 2σ(F²)] = 0.073
wR(F²) = 0.157
S = 1.00
4110 reflections
307 parameters
H-atom parameters constrained
Δρ_max = 0.13 e Å⁻³
Δρ_min = −0.13 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O4ⁱ	0.86	2.32	3.044 (4)	142
N2—H2C⋯O2	0.86	2.08	2.931 (4)	171
C19—H19A⋯Cg2ⁱⁱ	0.93	2.94	3.644 (4)	134
C23—H23A⋯Cg1ⁱⁱⁱ	0.93	2.97	3.710 (5)	138
Symmetry codes: (i) x-1, y-1, z; (ii) x, y+1, z; (iii) x+1, y+1, z. Cg1 and Cg2 are the centroids of the C1–C6 and C8–C13 rings, respectively.

Data collection: CAD-4 Software (Enraf–Nonius, 1989 ); 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: SHELXTL (Sheldrick, 2008).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809013312/hk2663sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809013312/hk2663Isup2.hkl

checkCIF report

Comment top

Some derivatives of aniline are important chemical materials. We report herein the crystal structure of the title compound.

The asymmetric unit of the title compound contains two crystallographically independent molecules (Fig. 1), in which the bond lengths (Allen et al., 1987) and angles are within normal ranges. Rings A (C1-C6), B (C8-C13) and A' (C14-C19), B' (C21-C26) are, of course, planar, and they are oriented at dihedral angles of A/B = 61.77 (3) and A'/B' = 53.94 (3) °. Intramolecular N-H···O hydrogen bond (Table 1) links the molecules.

In the crystal structure, intra- and intermolecular N-H···O hydrogen bonds (Table 1) link the molecules into chains (Fig. 2), in which they may be effective in the stabilization of the structure. There also exist weak C—H···π interactions (Table 1).

Related literature top

For a related structure, see: Hynes et al. (2008). For bond-length data, see: Allen et al. (1987). Cg1 and Cg2 are the centroids of the C1–C6 and C8–C13 rings, respectively.

Experimental top

For the preparation of the title compound, phenyl chloroformate (1.0 ml) was added slowly to a cold solution of 4-fluorbenzenamine (1.0 g) and triethylamine (0.8 ml) in methylene chloride (10 ml) at 273 K. The mixture was then warmed and stirred for 1 h at room temperature. It was washed with water (20 ml), dried and concentrated to give the title compound (yield; 1.3 g) (Hynes et al., 2008). Crystals suitable for X-ray analysis were obtained by slow evaporation of a methanol solution.

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software (Enraf–Nonius, 1989); 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: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title molecule, with the atom-numbering scheme. Hydrogen bond is shown as dashed line.
	Fig. 2. A partial packing diagram of the title compound. Hydrogen bonds are shown as dashed lines.

Phenyl N-(4-fluorophenyl)carbamate top

Crystal data top

C₁₃H₁₀FNO₂	Z = 4
M_r = 231.22	F(000) = 480
Triclinic, P1	D_x = 1.353 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.8860 (12) Å	Cell parameters from 25 reflections
b = 7.8540 (16) Å	θ = 8–12°
c = 24.761 (5) Å	µ = 0.10 mm⁻¹
α = 96.62 (3)°	T = 294 K
β = 92.82 (3)°	Block, colorless
γ = 91.19 (3)°	0.10 × 0.10 × 0.08 mm
V = 1135.3 (4) Å³

Data collection top

Enraf–Nonius CAD-4 diffractometer	1662 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.060
Graphite monochromator	θ_max = 25.3°, θ_min = 1.7°
ω/2θ scans	h = 0→7
Absorption correction: ψ scan (North et al., 1968)	k = −9→9
T_min = 0.990, T_max = 0.992	l = −29→29
4548 measured reflections	3 standard reflections every 120 min
4110 independent reflections	intensity decay: 1%

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)] = 0.073	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.157	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.052P)²] where P = (F_o² + 2F_c²)/3
4110 reflections	(Δ/σ)_max < 0.001
307 parameters	Δρ_max = 0.13 e Å⁻³
0 restraints	Δρ_min = −0.13 e Å⁻³

Crystal data top

C₁₃H₁₀FNO₂	γ = 91.19 (3)°
M_r = 231.22	V = 1135.3 (4) Å³
Triclinic, P1	Z = 4
a = 5.8860 (12) Å	Mo Kα radiation
b = 7.8540 (16) Å	µ = 0.10 mm⁻¹
c = 24.761 (5) Å	T = 294 K
α = 96.62 (3)°	0.10 × 0.10 × 0.08 mm
β = 92.82 (3)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	1662 reflections with I > 2σ(I)
Absorption correction: ψ scan (North et al., 1968)	R_int = 0.060
T_min = 0.990, T_max = 0.992	3 standard reflections every 120 min
4548 measured reflections	intensity decay: 1%
4110 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.073	0 restraints
wR(F²) = 0.157	H-atom parameters constrained
S = 1.00	Δρ_max = 0.13 e Å⁻³
4110 reflections	Δρ_min = −0.13 e Å⁻³
307 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
N1	0.0390 (6)	−0.6473 (4)	0.26993 (14)	0.0831 (11)
H1A	−0.0691	−0.7213	0.2599	0.100*
N2	0.6939 (5)	−0.2644 (4)	0.22504 (13)	0.0755 (11)
H2C	0.6083	−0.3507	0.2300	0.091*
F1	−0.0366 (5)	−0.3165 (3)	0.47653 (11)	0.1065 (9)
F2	1.1428 (5)	−0.3284 (4)	0.03482 (12)	0.1253 (11)
O1	0.1510 (5)	−0.7508 (4)	0.19019 (13)	0.1045 (12)
O2	0.3575 (5)	−0.5355 (4)	0.23766 (11)	0.0916 (10)
O3	0.5300 (5)	−0.1536 (4)	0.29759 (12)	0.0938 (11)
O4	0.8164 (4)	−0.0021 (3)	0.26628 (10)	0.0724 (8)
C1	0.3835 (12)	−0.7830 (7)	0.0572 (2)	0.1033 (18)
H1B	0.3416	−0.7637	0.0218	0.124*
C2	0.2332 (9)	−0.7392 (6)	0.0984 (3)	0.0934 (16)
H2A	0.0941	−0.6896	0.0917	0.112*
C3	0.3045 (9)	−0.7740 (6)	0.1487 (2)	0.0763 (14)
C4	0.5077 (11)	−0.8420 (6)	0.1599 (2)	0.0894 (16)
H4A	0.5516	−0.8605	0.1953	0.107*
C5	0.6465 (9)	−0.8828 (6)	0.1186 (3)	0.1024 (18)
H5A	0.7849	−0.9327	0.1259	0.123*
C6	0.5889 (11)	−0.8528 (7)	0.0673 (3)	0.108 (2)
H6A	0.6871	−0.8792	0.0394	0.130*
C7	0.1980 (8)	−0.6340 (6)	0.23447 (19)	0.0860 (15)
C8	0.0241 (7)	−0.5556 (5)	0.32213 (17)	0.0698 (12)
C9	−0.1636 (7)	−0.5849 (5)	0.35086 (18)	0.0740 (12)
H9A	−0.2782	−0.6603	0.3349	0.089*
C10	−0.1859 (8)	−0.5051 (6)	0.4028 (2)	0.0861 (14)
H10A	−0.3134	−0.5253	0.4221	0.103*
C11	−0.0157 (8)	−0.3963 (5)	0.42483 (19)	0.0776 (13)
C12	0.1691 (8)	−0.3626 (5)	0.39833 (18)	0.0772 (13)
H12A	0.2818	−0.2868	0.4150	0.093*
C13	0.1923 (7)	−0.4407 (5)	0.34595 (18)	0.0784 (13)
H13A	0.3192	−0.4165	0.3269	0.094*
C14	0.4753 (10)	0.1478 (6)	0.4438 (2)	0.0860 (15)
H14A	0.4594	0.2114	0.4774	0.103*
C15	0.6668 (9)	0.0580 (6)	0.4346 (2)	0.0882 (15)
H15A	0.7815	0.0618	0.4620	0.106*
C16	0.6942 (7)	−0.0391 (5)	0.3851 (2)	0.0744 (13)
H16A	0.8265	−0.0994	0.3790	0.089*
C17	0.5254 (8)	−0.0445 (5)	0.34616 (18)	0.0647 (11)
C18	0.3329 (8)	0.0490 (6)	0.35436 (18)	0.0775 (13)
H18A	0.2203	0.0478	0.3266	0.093*
C19	0.3070 (9)	0.1455 (6)	0.4044 (2)	0.0829 (14)
H19A	0.1761	0.2075	0.4107	0.099*
C20	0.6969 (7)	−0.1294 (6)	0.26345 (17)	0.0763 (13)
C21	0.8171 (7)	−0.2801 (5)	0.17706 (16)	0.0588 (10)
C22	1.0269 (7)	−0.2011 (5)	0.17460 (18)	0.0738 (12)
H22A	1.0954	−0.1378	0.2054	0.089*
C23	1.1343 (7)	−0.2167 (5)	0.12616 (19)	0.0798 (13)
H23A	1.2738	−0.1612	0.1237	0.096*
C24	1.0365 (9)	−0.3124 (6)	0.08250 (19)	0.0840 (14)
C25	0.8320 (8)	−0.3995 (5)	0.08437 (18)	0.0813 (13)
H25A	0.7693	−0.4681	0.0540	0.098*
C26	0.7227 (7)	−0.3818 (5)	0.13273 (17)	0.0717 (12)
H26A	0.5845	−0.4393	0.1352	0.086*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.078 (3)	0.080 (3)	0.086 (3)	−0.031 (2)	0.023 (2)	−0.013 (2)
N2	0.082 (3)	0.062 (2)	0.080 (3)	−0.038 (2)	0.023 (2)	−0.0024 (19)
F1	0.120 (2)	0.102 (2)	0.094 (2)	−0.0065 (17)	0.0279 (17)	−0.0139 (16)
F2	0.140 (3)	0.121 (2)	0.112 (2)	−0.0283 (19)	0.061 (2)	−0.0174 (18)
O1	0.105 (3)	0.109 (3)	0.091 (2)	−0.056 (2)	0.030 (2)	−0.027 (2)
O2	0.094 (2)	0.085 (2)	0.091 (2)	−0.0490 (18)	0.0269 (18)	−0.0119 (17)
O3	0.099 (2)	0.086 (2)	0.089 (2)	−0.0449 (18)	0.0397 (19)	−0.0265 (18)
O4	0.0745 (19)	0.0645 (18)	0.0752 (19)	−0.0264 (15)	0.0099 (15)	−0.0018 (14)
C1	0.112 (5)	0.125 (5)	0.071 (4)	−0.036 (4)	−0.012 (4)	0.014 (3)
C2	0.081 (4)	0.089 (4)	0.112 (5)	−0.014 (3)	−0.010 (4)	0.030 (3)
C3	0.065 (3)	0.070 (3)	0.090 (4)	−0.027 (3)	0.014 (3)	−0.005 (3)
C4	0.099 (4)	0.083 (4)	0.083 (4)	−0.035 (3)	−0.008 (3)	0.008 (3)
C5	0.080 (4)	0.063 (3)	0.163 (6)	−0.007 (3)	−0.009 (5)	0.013 (4)
C6	0.081 (4)	0.102 (5)	0.134 (6)	−0.029 (4)	0.032 (4)	−0.025 (4)
C7	0.081 (4)	0.093 (4)	0.077 (3)	−0.033 (3)	0.015 (3)	−0.015 (3)
C8	0.069 (3)	0.062 (3)	0.079 (3)	−0.017 (2)	0.015 (2)	0.008 (2)
C9	0.066 (3)	0.067 (3)	0.087 (3)	−0.016 (2)	0.010 (2)	0.002 (2)
C10	0.083 (3)	0.078 (3)	0.097 (4)	−0.013 (3)	0.025 (3)	0.006 (3)
C11	0.081 (4)	0.061 (3)	0.089 (4)	0.005 (3)	0.024 (3)	−0.007 (3)
C12	0.081 (3)	0.074 (3)	0.076 (3)	−0.015 (3)	0.000 (3)	0.009 (3)
C13	0.075 (3)	0.077 (3)	0.082 (3)	−0.030 (2)	0.009 (2)	0.006 (3)
C14	0.093 (4)	0.086 (4)	0.078 (4)	−0.010 (3)	0.020 (3)	0.002 (3)
C15	0.090 (4)	0.098 (4)	0.077 (4)	−0.012 (3)	0.002 (3)	0.018 (3)
C16	0.055 (3)	0.064 (3)	0.108 (4)	−0.001 (2)	0.015 (3)	0.020 (3)
C17	0.065 (3)	0.057 (3)	0.072 (3)	−0.014 (2)	0.012 (3)	0.005 (2)
C18	0.077 (4)	0.078 (3)	0.079 (3)	−0.020 (3)	−0.004 (3)	0.021 (3)
C19	0.080 (4)	0.069 (3)	0.102 (4)	0.013 (3)	0.022 (3)	0.008 (3)
C20	0.081 (3)	0.070 (3)	0.076 (3)	−0.028 (3)	0.017 (3)	−0.003 (3)
C21	0.059 (3)	0.048 (2)	0.068 (3)	−0.007 (2)	0.003 (2)	0.002 (2)
C22	0.054 (3)	0.073 (3)	0.090 (3)	−0.018 (2)	0.002 (2)	−0.005 (2)
C23	0.068 (3)	0.070 (3)	0.099 (4)	−0.010 (2)	0.029 (3)	−0.007 (3)
C24	0.099 (4)	0.070 (3)	0.082 (4)	−0.006 (3)	0.032 (3)	−0.006 (3)
C25	0.093 (4)	0.073 (3)	0.074 (3)	−0.006 (3)	0.009 (3)	−0.008 (2)
C26	0.072 (3)	0.065 (3)	0.074 (3)	−0.018 (2)	0.007 (2)	−0.007 (2)

Geometric parameters (Å, º) top

N1—C7	1.325 (5)	C9—H9A	0.9300
N1—C8	1.413 (4)	C10—C11	1.354 (5)
N1—H1A	0.8600	C10—H10A	0.9300
N2—C20	1.340 (4)	C11—C12	1.335 (5)
N2—C21	1.417 (4)	C12—C13	1.384 (5)
N2—H2C	0.8600	C12—H12A	0.9300
F1—C11	1.371 (4)	C13—H13A	0.9300
F2—C24	1.358 (4)	C14—C19	1.354 (6)
O1—C3	1.399 (5)	C14—C15	1.357 (6)
O1—C7	1.359 (4)	C14—H14A	0.9300
O2—C7	1.198 (4)	C15—C16	1.385 (6)
O3—C17	1.396 (5)	C15—H15A	0.9300
O3—C20	1.351 (4)	C16—C17	1.347 (5)
O4—C20	1.204 (4)	C16—H16A	0.9300
C1—C6	1.361 (7)	C17—C18	1.374 (5)
C1—C2	1.400 (6)	C18—C19	1.393 (6)
C1—H1B	0.9300	C18—H18A	0.9300
C2—C3	1.355 (6)	C19—H19A	0.9300
C2—H2A	0.9300	C21—C26	1.368 (5)
C3—C4	1.349 (6)	C21—C22	1.377 (5)
C4—C5	1.353 (6)	C22—C23	1.377 (5)
C4—H4A	0.9300	C22—H22A	0.9300
C5—C6	1.348 (7)	C23—C24	1.341 (5)
C5—H5A	0.9300	C23—H23A	0.9300
C6—H6A	0.9300	C24—C25	1.377 (6)
C8—C9	1.373 (5)	C25—C26	1.381 (5)
C8—C13	1.388 (5)	C25—H25A	0.9300
C9—C10	1.379 (5)	C26—H26A	0.9300

C7—N1—C8	128.3 (4)	C13—C12—H12A	120.1
C7—N1—H1A	115.8	C12—C13—C8	119.2 (4)
C8—N1—H1A	115.8	C12—C13—H13A	120.4
C20—N2—C21	126.8 (3)	C8—C13—H13A	120.4
C20—N2—H2C	116.6	C19—C14—C15	120.5 (5)
C21—N2—H2C	116.6	C19—C14—H14A	119.7
C7—O1—C3	120.4 (3)	C15—C14—H14A	119.7
C20—O3—C17	118.5 (3)	C14—C15—C16	121.0 (5)
C6—C1—C2	122.3 (5)	C14—C15—H15A	119.5
C6—C1—H1B	118.9	C16—C15—H15A	119.5
C2—C1—H1B	118.9	C17—C16—C15	118.7 (4)
C3—C2—C1	115.4 (5)	C17—C16—H16A	120.6
C3—C2—H2A	122.3	C15—C16—H16A	120.6
C1—C2—H2A	122.3	C16—C17—C18	120.9 (4)
C4—C3—C2	123.5 (5)	C16—C17—O3	121.9 (5)
C4—C3—O1	118.5 (6)	C18—C17—O3	117.0 (4)
C2—C3—O1	117.8 (6)	C17—C18—C19	119.7 (4)
C3—C4—C5	118.9 (5)	C17—C18—H18A	120.1
C3—C4—H4A	120.6	C19—C18—H18A	120.1
C5—C4—H4A	120.6	C14—C19—C18	119.0 (5)
C6—C5—C4	121.5 (6)	C14—C19—H19A	120.5
C6—C5—H5A	119.2	C18—C19—H19A	120.5
C4—C5—H5A	119.2	O4—C20—N2	127.1 (4)
C5—C6—C1	118.4 (6)	O4—C20—O3	124.4 (4)
C5—C6—H6A	120.8	N2—C20—O3	108.3 (3)
C1—C6—H6A	120.8	C26—C21—C22	120.3 (4)
O2—C7—N1	128.5 (4)	C26—C21—N2	117.4 (3)
O2—C7—O1	122.5 (4)	C22—C21—N2	122.3 (4)
N1—C7—O1	109.0 (4)	C21—C22—C23	119.4 (4)
C9—C8—C13	118.8 (4)	C21—C22—H22A	120.3
C9—C8—N1	118.1 (4)	C23—C22—H22A	120.3
C13—C8—N1	123.0 (4)	C24—C23—C22	119.6 (4)
C8—C9—C10	121.4 (4)	C24—C23—H23A	120.2
C8—C9—H9A	119.3	C22—C23—H23A	120.2
C10—C9—H9A	119.3	C23—C24—F2	119.6 (4)
C11—C10—C9	117.7 (4)	C23—C24—C25	122.3 (4)
C11—C10—H10A	121.2	F2—C24—C25	118.1 (4)
C9—C10—H10A	121.2	C24—C25—C26	118.1 (4)
C12—C11—C10	123.0 (4)	C24—C25—H25A	121.0
C12—C11—F1	118.9 (4)	C26—C25—H25A	121.0
C10—C11—F1	118.1 (4)	C21—C26—C25	120.2 (4)
C11—C12—C13	119.8 (4)	C21—C26—H26A	119.9
C11—C12—H12A	120.1	C25—C26—H26A	119.9

C6—C1—C2—C3	−1.2 (7)	C19—C14—C15—C16	−0.6 (7)
C1—C2—C3—C4	1.7 (7)	C14—C15—C16—C17	−0.7 (6)
C1—C2—C3—O1	−173.0 (4)	C15—C16—C17—C18	2.3 (6)
C7—O1—C3—C4	67.3 (6)	C15—C16—C17—O3	−173.0 (3)
C7—O1—C3—C2	−117.7 (5)	C20—O3—C17—C16	−63.8 (6)
C2—C3—C4—C5	−2.0 (7)	C20—O3—C17—C18	120.8 (4)
O1—C3—C4—C5	172.7 (4)	C16—C17—C18—C19	−2.6 (6)
C3—C4—C5—C6	1.8 (7)	O3—C17—C18—C19	172.9 (4)
C4—C5—C6—C1	−1.3 (8)	C15—C14—C19—C18	0.3 (7)
C2—C1—C6—C5	1.1 (8)	C17—C18—C19—C14	1.3 (6)
C8—N1—C7—O2	−4.2 (9)	C21—N2—C20—O4	−5.8 (8)
C8—N1—C7—O1	177.7 (4)	C21—N2—C20—O3	170.2 (4)
C3—O1—C7—O2	7.6 (8)	C17—O3—C20—O4	−15.0 (7)
C3—O1—C7—N1	−174.2 (4)	C17—O3—C20—N2	168.9 (4)
C7—N1—C8—C9	176.8 (5)	C20—N2—C21—C26	−150.6 (4)
C7—N1—C8—C13	−4.7 (7)	C20—N2—C21—C22	31.2 (6)
C13—C8—C9—C10	−1.1 (7)	C26—C21—C22—C23	4.0 (6)
N1—C8—C9—C10	177.5 (4)	N2—C21—C22—C23	−177.8 (4)
C8—C9—C10—C11	−0.1 (7)	C21—C22—C23—C24	−1.9 (7)
C9—C10—C11—C12	0.6 (7)	C22—C23—C24—F2	−179.7 (4)
C9—C10—C11—F1	−180.0 (4)	C22—C23—C24—C25	−1.2 (8)
C10—C11—C12—C13	0.0 (8)	C23—C24—C25—C26	2.1 (7)
F1—C11—C12—C13	−179.4 (4)	F2—C24—C25—C26	−179.4 (4)
C11—C12—C13—C8	−1.1 (7)	C22—C21—C26—C25	−3.1 (6)
C9—C8—C13—C12	1.6 (7)	N2—C21—C26—C25	178.6 (4)
N1—C8—C13—C12	−176.9 (4)	C24—C25—C26—C21	0.1 (7)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O4ⁱ	0.86	2.32	3.044 (4)	142
N2—H2C···O2	0.86	2.08	2.931 (4)	171
C19—H19A···Cg2ⁱⁱ	0.93	2.94	3.644 (4)	134
C23—H23A···Cg1ⁱⁱⁱ	0.93	2.97	3.710 (5)	138

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

Experimental details

Crystal data
Chemical formula	C₁₃H₁₀FNO₂
M_r	231.22
Crystal system, space group	Triclinic, P1
Temperature (K)	294
a, b, c (Å)	5.8860 (12), 7.8540 (16), 24.761 (5)
α, β, γ (°)	96.62 (3), 92.82 (3), 91.19 (3)
V (Å³)	1135.3 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.10 × 0.10 × 0.08

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.990, 0.992
No. of measured, independent and observed [I > 2σ(I)] reflections	4548, 4110, 1662
R_int	0.060
(sin θ/λ)_max (Å⁻¹)	0.601

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.073, 0.157, 1.00
No. of reflections	4110
No. of parameters	307
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.13, −0.13

Computer programs: CAD-4 Software (Enraf–Nonius, 1989), XCAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O4ⁱ	0.86	2.32	3.044 (4)	142.00
N2—H2C···O2	0.86	2.08	2.931 (4)	171.00
C19—H19A···Cg2ⁱⁱ	0.93	2.94	3.644 (4)	133.71
C23—H23A···Cg1ⁱⁱⁱ	0.93	2.97	3.710 (5)	137.68

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

Acknowledgements

The authors thank 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. CrossRef Web of Science Google Scholar
Enraf–Nonius (1989). CAD-4 Software. Enraf–Nonius, Delft. The Netherlands. Google Scholar
Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany. Google Scholar
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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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Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar