Phenyl N-phenyl-carbamate.

In the title compound, C(13)H(11)NO(2), the aromatic rings are oriented at a dihedral angle of 42.52 (12)°. The crystal structure is stabilized by inter-molecular N-H⋯O hydrogen bonds, which form infinite one-dimensional polymeric chains extending along the a axis. C-H⋯π inter-actions between the aromatic rings are also present.

Related literature

For related structures, see: Haufe et al. (2003 ▶); Shah et al. (2008 ▶, 2009 ▶); Xu & Qu (2008 ▶).

Experimental

Crystal data

C13H11NO2

M = 213.23

Orthorhombic,

a = 9.4734 (9) Å

b = 19.5825 (17) Å

c = 5.8509 (5) Å

V = 1085.42 (17) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 296 K

0.22 × 0.12 × 0.12 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.985, T max = 0.988

6579 measured reflections

1505 independent reflections

751 reflections with I > 2σ(I)

R int = 0.071

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.086

S = 0.97

1505 reflections

145 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.13 e Å−3

Δρmin = −0.17 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809017887/at2785sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809017887/at2785Isup2.hkl

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

C13H11NO2	F(000) = 448
Mr = 213.23	Dx = 1.305 Mg m−3
Orthorhombic, Pna21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 2241 reflections
a = 9.4734 (9) Å	θ = 3.0–28.6°
b = 19.5825 (17) Å	µ = 0.09 mm−1
c = 5.8509 (5) Å	T = 296 K
V = 1085.42 (17) Å3	Needle, colourless
Z = 4	0.22 × 0.12 × 0.12 mm

Bruker Kappa APEXII CCD diffractometer	1505 independent reflections
Radiation source: fine-focus sealed tube	751 reflections with I > 2σ(I)
graphite	Rint = 0.071
Detector resolution: 7.40 pixels mm-1	θmax = 28.6°, θmin = 3.0°
ω scans	h = −12→12
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −26→26
Tmin = 0.985, Tmax = 0.988	l = −4→7
6579 measured reflections

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.086	H-atom parameters constrained
S = 0.97	w = 1/[σ2(Fo2) + (0.028P)2] where P = (Fo2 + 2Fc2)/3
1505 reflections	(Δ/σ)max < 0.001
145 parameters	Δρmax = 0.13 e Å−3
1 restraint	Δρmin = −0.16 e Å−3

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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
O1	0.2597 (2)	0.32604 (11)	0.9484 (4)	0.0567 (9)
O2	0.0419 (2)	0.29274 (9)	0.8340 (5)	0.0516 (8)
N1	0.2427 (3)	0.23828 (12)	0.7187 (5)	0.0452 (10)
C1	0.2055 (3)	0.37847 (16)	1.0868 (7)	0.0443 (14)
C2	0.2411 (4)	0.44407 (15)	1.0327 (7)	0.0510 (14)
C3	0.2016 (4)	0.49574 (16)	1.1764 (7)	0.0573 (15)
C4	0.1281 (4)	0.48187 (15)	1.3717 (7)	0.0553 (14)
C5	0.0927 (4)	0.41549 (16)	1.4235 (7)	0.0550 (14)
C6	0.1333 (4)	0.36338 (15)	1.2818 (7)	0.0489 (13)
C7	0.1675 (3)	0.28518 (15)	0.8343 (7)	0.0422 (11)
C8	0.1863 (3)	0.19143 (14)	0.5605 (7)	0.0414 (13)
C9	0.0627 (3)	0.15661 (14)	0.5992 (6)	0.0486 (13)
C10	0.0146 (4)	0.11085 (16)	0.4366 (8)	0.0633 (18)
C11	0.0904 (5)	0.09913 (18)	0.2388 (8)	0.0700 (16)
C12	0.2135 (5)	0.13340 (19)	0.2040 (7)	0.0667 (18)
C13	0.2617 (4)	0.17989 (15)	0.3606 (7)	0.0548 (13)
H1	0.33213	0.23677	0.74330	0.0544*
H2	0.29156	0.45348	0.90007	0.0616*
H3	0.22491	0.54063	1.14082	0.0689*
H4	0.10216	0.51715	1.46947	0.0664*
H5	0.04108	0.40599	1.55489	0.0657*
H6	0.11184	0.31833	1.31818	0.0584*
H9	0.01197	0.16370	0.73313	0.0581*
H10	−0.06985	0.08773	0.46083	0.0757*
H11	0.05769	0.06814	0.13063	0.0838*
H12	0.26557	0.12516	0.07208	0.0799*
H13	0.34490	0.20372	0.33304	0.0658*

	U11	U22	U33	U12	U13	U23
O1	0.0340 (14)	0.0611 (13)	0.0751 (19)	−0.0041 (12)	0.0042 (13)	−0.0266 (14)
O2	0.0283 (12)	0.0562 (12)	0.0702 (18)	0.0033 (11)	−0.0034 (13)	−0.0119 (12)
N1	0.0287 (15)	0.0489 (15)	0.058 (2)	0.0041 (14)	−0.0041 (15)	−0.0099 (15)
C1	0.032 (2)	0.052 (2)	0.049 (3)	−0.0012 (16)	−0.003 (2)	−0.0058 (19)
C2	0.050 (2)	0.054 (2)	0.049 (3)	−0.0063 (18)	0.000 (2)	0.0073 (19)
C3	0.059 (3)	0.0410 (19)	0.072 (3)	−0.0043 (17)	−0.002 (2)	0.006 (2)
C4	0.053 (2)	0.049 (2)	0.064 (3)	0.0016 (17)	−0.001 (2)	−0.0118 (19)
C5	0.055 (2)	0.059 (2)	0.051 (3)	−0.0031 (17)	0.006 (2)	0.001 (2)
C6	0.048 (2)	0.0386 (17)	0.060 (3)	−0.0006 (16)	−0.002 (2)	0.0033 (19)
C7	0.040 (2)	0.0385 (15)	0.048 (2)	−0.0018 (17)	−0.007 (2)	0.0020 (17)
C8	0.039 (2)	0.0362 (17)	0.049 (3)	0.0063 (15)	−0.006 (2)	−0.0044 (17)
C9	0.043 (2)	0.0437 (17)	0.059 (3)	−0.0001 (16)	−0.0045 (19)	−0.0024 (18)
C10	0.049 (3)	0.053 (2)	0.088 (4)	−0.0040 (18)	−0.021 (3)	−0.008 (2)
C11	0.079 (3)	0.062 (2)	0.069 (3)	0.014 (2)	−0.024 (3)	−0.022 (2)
C12	0.077 (4)	0.069 (2)	0.054 (3)	0.019 (2)	−0.002 (3)	−0.012 (2)
C13	0.052 (2)	0.0485 (18)	0.064 (3)	0.0044 (17)	0.007 (2)	−0.004 (2)

O1—C1	1.405 (4)	C9—C10	1.384 (5)
O1—C7	1.360 (4)	C10—C11	1.381 (6)
O2—C7	1.199 (3)	C11—C12	1.361 (6)
N1—C7	1.345 (4)	C12—C13	1.370 (5)
N1—C8	1.409 (4)	C2—H2	0.9300
N1—H1	0.8600	C3—H3	0.9300
C1—C2	1.365 (4)	C4—H4	0.9300
C1—C6	1.363 (5)	C5—H5	0.9300
C2—C3	1.368 (5)	C6—H6	0.9300
C3—C4	1.365 (6)	C9—H9	0.9300
C4—C5	1.376 (4)	C10—H10	0.9300
C5—C6	1.370 (5)	C11—H11	0.9300
C8—C13	1.389 (5)	C12—H12	0.9300
C8—C9	1.374 (4)	C13—H13	0.9300
O2···C6	3.087 (5)	C10···H3ix	3.0700
O2···C9	3.005 (4)	C13···H6iii	3.0700
O2···N1i	2.976 (3)	H1···H13	2.4900
O1···H9ii	2.7100	H1···O2ii	2.1400
O2···H5iii	2.7500	H1···H9ii	2.5900
O2···H9	2.6100	H3···C9x	3.0400
O2···H1i	2.1400	H3···C10x	3.0700
N1···O2ii	2.976 (3)	H4···H12xi	2.5300
C1···C10iv	3.579 (5)	H5···O2v	2.7500
C5···C7v	3.576 (5)	H5···C3xii	3.0800
C6···O2	3.087 (5)	H6···C7	2.9500
C6···C7v	3.592 (6)	H6···C8v	2.9500
C7···C6iii	3.592 (6)	H6···C13v	3.0700
C7···C5iii	3.576 (5)	H6···H13viii	2.5700
C9···O2	3.005 (4)	H9···O2	2.6100
C10···C1vi	3.579 (5)	H9···C7	2.8600
C2···H11iv	3.0600	H9···O1i	2.7100
C3···H5vii	3.0800	H9···H1i	2.5900
C6···H13viii	3.0500	H11···C2vi	3.0600
C7···H9	2.8600	H12···H4xiii	2.5300
C7···H6	2.9500	H13···H1	2.4900
C8···H6iii	2.9500	H13···C6xiv	3.0500
C9···H3ix	3.0400	H13···H6xiv	2.5700
C1—O1—C7	118.6 (2)	C8—C13—C12	120.0 (3)
C7—N1—C8	125.1 (3)	C1—C2—H2	120.00
C7—N1—H1	117.00	C3—C2—H2	120.00
C8—N1—H1	117.00	C2—C3—H3	120.00
O1—C1—C2	117.6 (3)	C4—C3—H3	120.00
O1—C1—C6	120.5 (3)	C3—C4—H4	120.00
C2—C1—C6	121.5 (3)	C5—C4—H4	120.00
C1—C2—C3	119.1 (4)	C4—C5—H5	120.00
C2—C3—C4	120.5 (3)	C6—C5—H5	120.00
C3—C4—C5	119.8 (3)	C1—C6—H6	120.00
C4—C5—C6	120.1 (4)	C5—C6—H6	120.00
C1—C6—C5	119.1 (3)	C8—C9—H9	120.00
O1—C7—O2	124.4 (3)	C10—C9—H9	120.00
O1—C7—N1	108.0 (2)	C9—C10—H10	120.00
O2—C7—N1	127.5 (3)	C11—C10—H10	120.00
N1—C8—C9	122.6 (3)	C10—C11—H11	120.00
C9—C8—C13	119.8 (3)	C12—C11—H11	120.00
N1—C8—C13	117.7 (3)	C11—C12—H12	120.00
C8—C9—C10	119.3 (3)	C13—C12—H12	120.00
C9—C10—C11	120.8 (3)	C8—C13—H13	120.00
C10—C11—C12	119.3 (4)	C12—C13—H13	120.00
C11—C12—C13	120.9 (4)
C7—O1—C1—C2	−119.0 (3)	C1—C2—C3—C4	0.3 (6)
C7—O1—C1—C6	68.1 (4)	C2—C3—C4—C5	−0.4 (6)
C1—O1—C7—O2	3.9 (5)	C3—C4—C5—C6	1.2 (6)
C1—O1—C7—N1	−178.6 (3)	C4—C5—C6—C1	−1.8 (6)
C8—N1—C7—O1	−172.7 (3)	N1—C8—C9—C10	−179.4 (3)
C7—N1—C8—C13	138.2 (3)	C13—C8—C9—C10	−0.6 (5)
C8—N1—C7—O2	4.7 (6)	N1—C8—C13—C12	178.2 (3)
C7—N1—C8—C9	−43.0 (5)	C9—C8—C13—C12	−0.7 (5)
O1—C1—C2—C3	−173.7 (3)	C8—C9—C10—C11	1.1 (5)
C2—C1—C6—C5	1.6 (6)	C9—C10—C11—C12	−0.3 (6)
C6—C1—C2—C3	−0.9 (6)	C10—C11—C12—C13	−1.0 (6)
O1—C1—C6—C5	174.2 (3)	C11—C12—C13—C8	1.5 (6)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2ii	0.8600	2.1400	2.976 (3)	165.00
C3—H3···Cg2x	0.9300	2.8000	3.673 (4)	156.00
C10—H10···Cg1vi	0.9300	2.8600	3.599 (4)	137.00

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O2i	0.86	2.14	2.976 (3)	165
C3—H3⋯Cg2ii	0.93	2.80	3.673 (4)	156
C10—H10⋯Cg1iii	0.93	2.86	3.599 (4)	137

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