Phenyl N-(4-fluorophen-yl)carbamate.

The asymmetric unit of the title compound, C(13)H(10)FNO(2), contains two crystallographically independent mol-ecules. The aromatic rings are oriented at dihedral angles of 61.77 (3) and 53.94 (3)° in the two mol-ecules. An N-H⋯O hydrogen bond links the mol-ecules. In the crystal structure, inter-molecular N-H⋯O hydrogen bonds link the mol-ecules into chains. Weak C-H⋯π inter-actions 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 = 231.22

Triclinic,

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[F 2 > 2σ(F 2)] = 0.073

wR(F 2) = 0.157

S = 1.00

4110 reflections

307 parameters

H-atom parameters constrained

Δρmax = 0.13 e Å−3

Δρmin = −0.13 e Å−3

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 ▶).

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

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

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C13H10FNO2	Z = 4
Mr = 231.22	F(000) = 480
Triclinic, P1	Dx = 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

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

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(Fo2) + (0.052P)2] where P = (Fo2 + 2Fc2)/3
4110 reflections	(Δ/σ)max < 0.001
307 parameters	Δρmax = 0.13 e Å−3
0 restraints	Δρmin = −0.13 e Å−3

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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

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) ; (ii) ; (iii) . Cg1 and Cg2 are the centroids of the C1–C6 and C8–C13 rings, respectively.