N-Phenyl-formamide.

There are two independent mol-ecules in the asymmetric unit of the title compound, C(7)H(7)NO. The conformation of the N-H bond in the structure is syn to the C=O bond in one of the mol-ecules and anti in the other. In the crystal, mol-ecules are packed into chains diagonally in the ac plane via N-H⋯O hydrogen bonds.

Related literature

For related structures, see: Gowda et al. (2006 ▶); Brown (1966 ▶). For our study of the effect of ring and side chain substitutions on the crystal structures of aromatic amides, see: Gowda et al. (2000 ▶, 2007 ▶, 2009 ▶).

Experimental

Crystal data

C7H7NO

M = 121.14

Monoclinic,

a = 30.923 (3) Å

b = 6.1737 (6) Å

c = 14.814 (1) Å

β = 113.14 (1)°

V = 2600.6 (4) Å3

Z = 16

Mo Kα radiation

μ = 0.08 mm−1

T = 298 K

0.48 × 0.44 × 0.40 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▶) T min = 0.966, T max = 0.969

8394 measured reflections

2383 independent reflections

1679 reflections with I > 2σ(I)

R int = 0.016

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.115

S = 1.12

2383 reflections

170 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.11 e Å−3

Δρmin = −0.10 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2009 ▶); data reduction: CrysAlis RED; 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.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809022776/rk2151sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809022776/rk2151Isup2.hkl

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

C7H7NO	F(000) = 1024
Mr = 121.14	Dx = 1.238 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 2475 reflections
a = 30.923 (3) Å	θ = 2.7–28.2°
b = 6.1737 (6) Å	µ = 0.08 mm−1
c = 14.814 (1) Å	T = 298 K
β = 113.14 (1)°	Needle, colourless
V = 2600.6 (4) Å3	0.48 × 0.44 × 0.40 mm
Z = 16

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	2383 independent reflections
Radiation source: Fine–focus sealed tube	1679 reflections with I > 2σ(I)
Graphite	Rint = 0.016
ω and φ scans	θmax = 25.4°, θmin = 2.8°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −37→36
Tmin = 0.966, Tmax = 0.969	k = −7→7
8394 measured reflections	l = −17→17

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)] = 0.037	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.115	w = 1/[σ2(Fo2) + (0.0651P)2] where P = (Fo2 + 2Fc2)/3
S = 1.12	(Δ/σ)max < 0.001
2383 reflections	Δρmax = 0.11 e Å−3
170 parameters	Δρmin = −0.10 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: 0.0028 (7)

Experimental. Absorption correction: CrysAlis RED (Oxford Diffraction, 2009); empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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	0.09999 (4)	0.21410 (18)	0.62537 (8)	0.0921 (4)
N1	0.04841 (4)	0.34831 (19)	0.47961 (9)	0.0694 (4)
H1N	0.0202 (6)	0.322 (2)	0.4332 (11)	0.083*
C1	0.07229 (4)	0.5289 (2)	0.46365 (9)	0.0561 (3)
C2	0.04734 (5)	0.6657 (3)	0.38753 (10)	0.0727 (4)
H2	0.0159	0.6367	0.3491	0.087*
C3	0.06857 (6)	0.8441 (3)	0.36825 (12)	0.0893 (5)
H3	0.0515	0.9351	0.3164	0.107*
C4	0.11462 (6)	0.8895 (3)	0.42461 (12)	0.0890 (5)
H4	0.1289	1.0119	0.4119	0.107*
C5	0.13948 (6)	0.7535 (3)	0.49972 (12)	0.0828 (5)
H5	0.1709	0.7834	0.5378	0.099*
C6	0.11890 (5)	0.5734 (2)	0.51989 (11)	0.0687 (4)
H6	0.1363	0.4818	0.5712	0.082*
C7	0.06296 (6)	0.2094 (2)	0.55435 (12)	0.0792 (5)
H7	0.0426	0.0966	0.5518	0.095*
O2	0.04140 (4)	0.2563 (2)	0.16582 (9)	0.0996 (4)
N2	0.11861 (4)	0.1904 (2)	0.22825 (8)	0.0628 (3)
H2N	0.1131 (5)	0.067 (3)	0.1994 (10)	0.075*
C8	0.16640 (5)	0.2389 (2)	0.28235 (9)	0.0565 (3)
C9	0.18179 (6)	0.4299 (3)	0.33258 (13)	0.0862 (5)
H9	0.1603	0.5369	0.3309	0.103*
C10	0.22921 (7)	0.4618 (3)	0.38543 (14)	0.1024 (6)
H10	0.2394	0.5901	0.4202	0.123*
C11	0.26131 (6)	0.3093 (3)	0.38760 (14)	0.0963 (6)
H11	0.2932	0.3324	0.4235	0.116*
C12	0.24605 (6)	0.1230 (3)	0.33668 (13)	0.0919 (5)
H12	0.2678	0.0184	0.3371	0.110*
C13	0.19895 (5)	0.0867 (2)	0.28451 (11)	0.0750 (4)
H13	0.1891	−0.0425	0.2503	0.090*
C14	0.08175 (6)	0.3109 (3)	0.21441 (12)	0.0771 (4)
H14	0.0867	0.4471	0.2436	0.093*

	U11	U22	U33	U12	U13	U23
O1	0.0813 (8)	0.0791 (7)	0.0881 (8)	−0.0120 (6)	0.0032 (6)	0.0215 (5)
N1	0.0527 (7)	0.0658 (8)	0.0743 (8)	−0.0096 (6)	0.0082 (6)	0.0067 (6)
C1	0.0522 (8)	0.0564 (8)	0.0570 (7)	−0.0001 (6)	0.0186 (6)	−0.0032 (6)
C2	0.0644 (9)	0.0780 (10)	0.0644 (9)	−0.0023 (7)	0.0131 (7)	0.0049 (7)
C3	0.1006 (14)	0.0823 (11)	0.0750 (10)	−0.0058 (10)	0.0236 (9)	0.0207 (9)
C4	0.0993 (14)	0.0849 (12)	0.0826 (11)	−0.0263 (10)	0.0355 (10)	0.0063 (9)
C5	0.0682 (10)	0.0902 (12)	0.0847 (11)	−0.0210 (9)	0.0242 (8)	0.0026 (9)
C6	0.0555 (8)	0.0699 (9)	0.0742 (9)	−0.0033 (7)	0.0184 (7)	0.0063 (7)
C7	0.0714 (10)	0.0648 (9)	0.0897 (11)	−0.0116 (8)	0.0189 (9)	0.0098 (8)
O2	0.0556 (7)	0.1164 (10)	0.1092 (9)	0.0152 (6)	0.0132 (6)	0.0123 (7)
N2	0.0567 (7)	0.0615 (7)	0.0645 (7)	0.0048 (6)	0.0175 (6)	−0.0040 (5)
C8	0.0557 (8)	0.0602 (8)	0.0522 (7)	−0.0013 (6)	0.0197 (6)	0.0026 (6)
C9	0.0790 (12)	0.0746 (10)	0.1005 (12)	−0.0037 (8)	0.0303 (9)	−0.0202 (9)
C10	0.0939 (14)	0.0939 (13)	0.1047 (13)	−0.0311 (11)	0.0233 (11)	−0.0271 (10)
C11	0.0647 (11)	0.1055 (15)	0.0999 (13)	−0.0158 (11)	0.0122 (9)	0.0068 (11)
C12	0.0601 (10)	0.0924 (12)	0.1119 (13)	0.0070 (9)	0.0218 (9)	0.0067 (10)
C13	0.0618 (9)	0.0680 (9)	0.0873 (10)	0.0029 (7)	0.0209 (8)	−0.0064 (7)
C14	0.0667 (11)	0.0739 (10)	0.0865 (11)	0.0132 (8)	0.0256 (9)	0.0104 (8)

O1—C7	1.2132 (17)	O2—C14	1.2178 (18)
N1—C7	1.3314 (19)	N2—C14	1.3082 (19)
N1—C1	1.4076 (17)	N2—C8	1.4089 (17)
N1—H1N	0.888 (16)	N2—H2N	0.857 (16)
C1—C2	1.3771 (19)	C8—C13	1.3684 (19)
C1—C6	1.3797 (18)	C8—C9	1.375 (2)
C2—C3	1.369 (2)	C9—C10	1.378 (2)
C2—H2	0.9300	C9—H9	0.9300
C3—C4	1.367 (2)	C10—C11	1.359 (3)
C3—H3	0.9300	C10—H10	0.9300
C4—C5	1.365 (2)	C11—C12	1.354 (3)
C4—H4	0.9300	C11—H11	0.9300
C5—C6	1.371 (2)	C12—C13	1.373 (2)
C5—H5	0.9300	C12—H12	0.9300
C6—H6	0.9300	C13—H13	0.9300
C7—H7	0.9300	C14—H14	0.9300
C7—N1—C1	128.45 (13)	C14—N2—C8	128.51 (14)
C7—N1—H1N	115.8 (10)	C14—N2—H2N	115.9 (10)
C1—N1—H1N	115.7 (10)	C8—N2—H2N	115.6 (10)
C2—C1—C6	119.24 (13)	C13—C8—C9	118.76 (14)
C2—C1—N1	117.46 (12)	C13—C8—N2	117.69 (12)
C6—C1—N1	123.29 (12)	C9—C8—N2	123.55 (13)
C3—C2—C1	120.27 (14)	C8—C9—C10	119.64 (16)
C3—C2—H2	119.9	C8—C9—H9	120.2
C1—C2—H2	119.9	C10—C9—H9	120.2
C4—C3—C2	120.51 (15)	C11—C10—C9	121.22 (17)
C4—C3—H3	119.7	C11—C10—H10	119.4
C2—C3—H3	119.7	C9—C10—H10	119.4
C5—C4—C3	119.30 (15)	C12—C11—C10	118.93 (17)
C5—C4—H4	120.4	C12—C11—H11	120.5
C3—C4—H4	120.4	C10—C11—H11	120.5
C4—C5—C6	121.06 (15)	C11—C12—C13	120.85 (17)
C4—C5—H5	119.5	C11—C12—H12	119.6
C6—C5—H5	119.5	C13—C12—H12	119.6
C5—C6—C1	119.62 (14)	C8—C13—C12	120.59 (15)
C5—C6—H6	120.2	C8—C13—H13	119.7
C1—C6—H6	120.2	C12—C13—H13	119.7
O1—C7—N1	126.94 (14)	O2—C14—N2	124.22 (16)
O1—C7—H7	116.5	O2—C14—H14	117.9
N1—C7—H7	116.5	N2—C14—H14	117.9
C7—N1—C1—C2	−171.26 (15)	C14—N2—C8—C13	−178.73 (14)
C7—N1—C1—C6	9.0 (2)	C14—N2—C8—C9	1.3 (2)
C6—C1—C2—C3	−0.2 (2)	C13—C8—C9—C10	−1.4 (2)
N1—C1—C2—C3	180.00 (14)	N2—C8—C9—C10	178.58 (15)
C1—C2—C3—C4	−0.5 (3)	C8—C9—C10—C11	1.1 (3)
C2—C3—C4—C5	0.8 (3)	C9—C10—C11—C12	0.0 (3)
C3—C4—C5—C6	−0.5 (3)	C10—C11—C12—C13	−0.8 (3)
C4—C5—C6—C1	−0.2 (2)	C9—C8—C13—C12	0.7 (2)
C2—C1—C6—C5	0.5 (2)	N2—C8—C13—C12	−179.34 (13)
N1—C1—C6—C5	−179.70 (14)	C11—C12—C13—C8	0.4 (3)
C1—N1—C7—O1	1.5 (3)	C8—N2—C14—O2	179.62 (13)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O2i	0.888 (16)	1.936 (16)	2.8239 (17)	178.1 (14)
N2—H2N···O1ii	0.857 (16)	2.007 (16)	2.8637 (17)	177.0 (14)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O2i	0.888 (16)	1.936 (16)	2.8239 (17)	178.1 (14)
N2—H2N⋯O1ii	0.857 (16)	2.007 (16)	2.8637 (17)	177.0 (14)

Symmetry codes: (i) ; (ii) .