N-(2,4,6-Trimethyl-phen-yl)formamide.

The title compound, C(10)H(13)NO, was obtained as the unexpected, almost exclusive, product in the attempted synthesis of a manganese(I)-N-heterocyclic carbene (NHC) complex. The dihedral angle between the planes of the formamide moiety and the aryl ring is 68.06 (10)°. In the crystal, mol-ecules are linked by N-H⋯O hydrogen bonds, forming infinite chains along the c axis.

Related literature

For background to formamide formation from NHCs, see: Denk et al. (2001 ▶). The rotation of the formamide entity out of the plane of the aryl ring and the hydrogen-bonding motif displayed by this structure are similar to those observed for the related compound N-(2,6-dimeth­yl)-formamide, see: Hanson et al. (2004 ▶); Omondi et al. (2005 ▶).

Experimental

Crystal data

C10H13NO

M = 163.21

Monoclinic,

a = 8.0659 (7) Å

b = 15.9004 (13) Å

c = 8.4290 (7) Å

β = 119.361 (1)°

V = 942.17 (14) Å3

Z = 4

Mo Kα radiation

μ = 0.07 mm−1

T = 293 K

0.44 × 0.38 × 0.28 mm

Data collection

Bruker (Siemens) P4 diffractometer fitted with a SMART 1K CCD detector

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.946, T max = 0.979

4988 measured reflections

1778 independent reflections

1607 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.138

S = 1.09

1778 reflections

161 parameters

All H-atom parameters refined

Δρmax = 0.21 e Å−3

Δρmin = −0.21 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL and SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: POV-RAY (Cason, 2004 ▶) and Mercury (Bruno et al., 2002 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810051469/bt5433sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810051469/bt5433Isup2.hkl

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

C10H13NO	F(000) = 352
Mr = 163.21	Dx = 1.151 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3714 reflections
a = 8.0659 (7) Å	θ = 2.8–26.4°
b = 15.9004 (13) Å	µ = 0.07 mm−1
c = 8.4290 (7) Å	T = 293 K
β = 119.361 (1)°	Prism, colourless
V = 942.17 (14) Å3	0.44 × 0.38 × 0.28 mm
Z = 4

Bruker P4 diffractometer	1778 independent reflections
Radiation source: fine-focus sealed tube	1607 reflections with I > 2σ(I)
graphite	Rint = 0.026
Detector resolution: 8.3 pixels mm-1	θmax = 26.4°, θmin = 2.6°
φ and ω scans	h = −9→10
Absorption correction: multi-scan (SADABS; Bruker, 2001)	k = −14→18
Tmin = 0.946, Tmax = 0.979	l = −10→5
4988 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)] = 0.048	Hydrogen site location: difference Fourier map
wR(F2) = 0.138	All H-atom parameters refined
S = 1.09	w = 1/[σ2(Fo2) + (0.0738P)2 + 0.186P] where P = (Fo2 + 2Fc2)/3
1778 reflections	(Δ/σ)max = 0.004
161 parameters	Δρmax = 0.21 e Å−3
0 restraints	Δρmin = −0.21 e Å−3
0 constraints

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 > 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
C1	0.7933 (2)	0.16285 (9)	0.08870 (17)	0.0407 (4)
C2	0.6198 (2)	0.16921 (10)	0.08652 (19)	0.0466 (4)
C3	0.5674 (2)	0.10396 (11)	0.1617 (2)	0.0509 (4)
H3	0.451 (3)	0.1097 (13)	0.161 (3)	0.072 (6)*
C4	0.6785 (2)	0.03318 (10)	0.2356 (2)	0.0488 (4)
C5	0.8489 (2)	0.02819 (9)	0.2331 (2)	0.0466 (4)
H5	0.934 (3)	−0.0186 (12)	0.288 (2)	0.055 (5)*
C6	0.9094 (2)	0.09227 (9)	0.16142 (18)	0.0421 (4)
C7	0.4899 (3)	0.24369 (15)	0.0026 (3)	0.0701 (5)
H7A	0.369 (5)	0.236 (2)	−0.009 (5)	0.139 (12)*
H7B	0.479 (4)	0.2576 (19)	−0.111 (5)	0.115 (9)*
H7C	0.530 (4)	0.292 (2)	0.078 (4)	0.111 (9)*
C8	0.6158 (4)	−0.03631 (15)	0.3157 (3)	0.0718 (6)
H8A	0.481 (5)	−0.056 (2)	0.237 (5)	0.132 (11)*
H8B	0.694 (6)	−0.085 (3)	0.348 (5)	0.152 (13)*
H8C	0.611 (4)	−0.0151 (19)	0.415 (5)	0.116 (9)*
C9	1.0959 (2)	0.08575 (13)	0.1626 (3)	0.0571 (4)
H9A	1.083 (3)	0.0893 (13)	0.040 (3)	0.073 (6)*
H9B	1.161 (4)	0.0329 (16)	0.214 (3)	0.088 (7)*
H9C	1.179 (3)	0.1299 (15)	0.234 (3)	0.078 (6)*
N1	0.85323 (19)	0.22763 (8)	0.01026 (18)	0.0489 (4)
H1	0.868 (3)	0.2161 (12)	−0.078 (3)	0.060 (5)*
C10	0.9063 (3)	0.30398 (11)	0.0798 (2)	0.0579 (5)
H10	0.947 (2)	0.3419 (11)	0.007 (2)	0.056 (5)*
O1	0.9086 (2)	0.33069 (8)	0.21640 (18)	0.0792 (5)

	U11	U22	U33	U12	U13	U23
C1	0.0488 (8)	0.0413 (7)	0.0360 (7)	−0.0034 (6)	0.0240 (6)	−0.0044 (5)
C2	0.0491 (8)	0.0497 (8)	0.0436 (8)	0.0045 (6)	0.0247 (6)	−0.0013 (6)
C3	0.0446 (8)	0.0618 (10)	0.0526 (8)	−0.0046 (7)	0.0287 (7)	−0.0060 (7)
C4	0.0568 (9)	0.0480 (8)	0.0452 (8)	−0.0113 (7)	0.0277 (7)	−0.0062 (6)
C5	0.0549 (9)	0.0397 (8)	0.0463 (8)	0.0015 (6)	0.0256 (7)	−0.0010 (6)
C6	0.0443 (7)	0.0450 (8)	0.0387 (7)	−0.0013 (6)	0.0218 (6)	−0.0057 (5)
C7	0.0683 (12)	0.0706 (13)	0.0771 (13)	0.0254 (10)	0.0400 (10)	0.0154 (11)
C8	0.0884 (15)	0.0662 (13)	0.0719 (12)	−0.0216 (11)	0.0480 (12)	0.0007 (10)
C9	0.0499 (9)	0.0671 (11)	0.0600 (10)	0.0033 (8)	0.0313 (8)	−0.0011 (8)
N1	0.0682 (8)	0.0471 (7)	0.0426 (7)	−0.0035 (6)	0.0359 (6)	−0.0011 (5)
C10	0.0854 (12)	0.0489 (9)	0.0507 (8)	−0.0124 (8)	0.0422 (9)	0.0005 (7)
O1	0.1406 (13)	0.0553 (8)	0.0656 (8)	−0.0296 (8)	0.0691 (9)	−0.0155 (6)

C1—C2	1.394 (2)	C7—H7B	0.95 (3)
C1—C6	1.396 (2)	C7—H7C	0.95 (3)
C1—N1	1.4303 (18)	C8—H8A	1.00 (4)
C2—C3	1.385 (2)	C8—H8B	0.95 (4)
C2—C7	1.508 (2)	C8—H8C	0.92 (3)
C3—C4	1.382 (2)	C9—H9A	0.99 (2)
C3—H3	0.94 (2)	C9—H9B	0.97 (3)
C4—C5	1.387 (2)	C9—H9C	0.95 (2)
C4—C8	1.506 (2)	N1—C10	1.325 (2)
C5—C6	1.390 (2)	N1—H1	0.83 (2)
C5—H5	0.96 (2)	C10—O1	1.219 (2)
C6—C9	1.503 (2)	C10—H10	1.023 (18)
C7—H7A	0.94 (4)
C2—C1—C6	121.16 (13)	C2—C7—H7C	113.3 (18)
C2—C1—N1	120.43 (13)	H7A—C7—H7C	100 (3)
C6—C1—N1	118.38 (13)	H7B—C7—H7C	109 (3)
C3—C2—C1	117.98 (14)	C4—C8—H8A	114.8 (19)
C3—C2—C7	120.32 (16)	C4—C8—H8B	114 (2)
C1—C2—C7	121.70 (15)	H8A—C8—H8B	107 (3)
C4—C3—C2	122.68 (14)	C4—C8—H8C	108.2 (19)
C4—C3—H3	120.4 (13)	H8A—C8—H8C	101 (3)
C2—C3—H3	117.0 (13)	H8B—C8—H8C	111 (3)
C3—C4—C5	117.91 (14)	C6—C9—H9A	113.2 (12)
C3—C4—C8	120.91 (16)	C6—C9—H9B	112.6 (14)
C5—C4—C8	121.18 (16)	H9A—C9—H9B	105.7 (19)
C4—C5—C6	121.78 (14)	C6—C9—H9C	110.0 (13)
C4—C5—H5	121.0 (11)	H9A—C9—H9C	107.6 (18)
C6—C5—H5	117.1 (11)	H9B—C9—H9C	107.3 (19)
C5—C6—C1	118.48 (13)	C10—N1—C1	124.38 (12)
C5—C6—C9	120.70 (14)	C10—N1—H1	116.2 (13)
C1—C6—C9	120.83 (14)	C1—N1—H1	119.1 (13)
C2—C7—H7A	113 (2)	O1—C10—N1	126.09 (15)
C2—C7—H7B	110.9 (19)	O1—C10—H10	120.0 (10)
H7A—C7—H7B	111 (3)	N1—C10—H10	113.9 (10)
C6—C1—C2—C3	1.1 (2)	C4—C5—C6—C1	−0.7 (2)
N1—C1—C2—C3	178.93 (13)	C4—C5—C6—C9	179.23 (14)
C6—C1—C2—C7	−177.86 (16)	C2—C1—C6—C5	−0.4 (2)
N1—C1—C2—C7	0.0 (2)	N1—C1—C6—C5	−178.22 (12)
C1—C2—C3—C4	−0.9 (2)	C2—C1—C6—C9	179.75 (14)
C7—C2—C3—C4	178.09 (16)	N1—C1—C6—C9	1.9 (2)
C2—C3—C4—C5	−0.1 (2)	C2—C1—N1—C10	70.1 (2)
C2—C3—C4—C8	−179.94 (16)	C6—C1—N1—C10	−112.01 (18)
C3—C4—C5—C6	0.9 (2)	C1—N1—C10—O1	−1.5 (3)
C8—C4—C5—C6	−179.26 (15)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1i	0.83 (2)	2.05 (2)	2.8775 (18)	171.4 (19)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1i	0.83 (2)	2.05 (2)	2.8775 (18)	171.4 (19)

Symmetry code: (i) .