N-(2,6-Diisopropyl-phen-yl)formamide.

The title compound, C(13)H(19)NO, exhibits a non-planar structure in which the 2,6-diisopropyl-phenyl ring is tilted at a dihedral angle of 77.4 (1)° with respect to the formamide group. This is the largest dihedral angle known among structurally characterized formamides. The mol-ecules are linked via N-H⋯O hydrogen bonds, forming infinite chains which run along the b-axis directions.

Related literature

For related literature, see: Boeyens et al. (1988 ▶); Ferguson et al. (1998 ▶); Gowda et al. (2000 ▶); Krishnamurthy (1982 ▶); LaPlanche & Rogers (1964 ▶); Omondi et al. (2005 ▶); Cerecetto et al. (2004 ▶); Chitanda et al. (2008 ▶).

Experimental

Crystal data

C13H19NO

M = 205.29

Monoclinic,

a = 8.9581 (15) Å

b = 8.7684 (15) Å

c = 15.840 (6) Å

β = 105.381 (10)°

V = 1199.6 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.07 mm−1

T = 173 (2) K

0.25 × 0.05 × 0.05 mm

Data collection

Nonius KappaCCD diffractometer

Absorption correction: none

7758 measured reflections

2365 independent reflections

1556 reflections with I > 2σ(I)

R int = 0.070

Refinement

R[F 2 > 2σ(F 2)] = 0.054

wR(F 2) = 0.128

S = 1.05

2365 reflections

140 parameters

H-atom parameters constrained

Δρmax = 0.15 e Å−3

Δρmin = −0.20 e Å−3

Data collection: COLLECT (Nonius, 1998 ▶); cell refinement: SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: DENZO (Otwinowski & Minor, 1997 ▶) and SCALEPACK; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808024811/bv2100sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808024811/bv2100Isup2.hkl

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

C13H19NO	F000 = 448
Mr = 205.29	Dx = 1.137 Mg m−3
Monoclinic, P21/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5165 reflections
a = 8.9581 (15) Å	θ = 1.0–27.5º
b = 8.7684 (15) Å	µ = 0.07 mm−1
c = 15.840 (6) Å	T = 173 (2) K
β = 105.381 (10)º	Rod, colourless
V = 1199.6 (5) Å3	0.25 × 0.05 × 0.05 mm
Z = 4

Nonius KappaCCD diffractometer	2365 independent reflections
Radiation source: fine-focus sealed tube	1556 reflections with I > 2σ(I)
Monochromator: horizonally mounted graphite crystal	Rint = 0.070
Detector resolution: 9 pixels mm-1	θmax = 26.0º
T = 173(2) K	θmin = 2.4º
φ scans and ω scans with κ offsets	h = −11→11
Absorption correction: none	k = −10→10
7758 measured reflections	l = −17→19

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)] = 0.054	H-atom parameters constrained
wR(F2) = 0.128	w = 1/[σ2(Fo2) + (0.0512P)2 + 0.2338P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max < 0.001
2365 reflections	Δρmax = 0.16 e Å−3
140 parameters	Δρmin = −0.20 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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	0.51988 (18)	0.05926 (16)	0.22728 (10)	0.0277 (4)
H1	0.5445	−0.0380	0.2282	0.033*
O1	0.40304 (16)	0.24069 (14)	0.29095 (9)	0.0385 (4)
C1	0.5662 (2)	0.15772 (18)	0.16592 (12)	0.0253 (4)
C2	0.7219 (2)	0.20161 (19)	0.18370 (13)	0.0276 (5)
C3	0.7655 (2)	0.2939 (2)	0.12239 (14)	0.0311 (5)
H3	0.8701	0.3260	0.1329	0.037*
C4	0.6582 (2)	0.3389 (2)	0.04654 (14)	0.0326 (5)
H4	0.6898	0.4012	0.0053	0.039*
C5	0.5059 (2)	0.2940 (2)	0.03028 (13)	0.0319 (5)
H5	0.4337	0.3255	−0.0223	0.038*
C6	0.4557 (2)	0.20300 (19)	0.08966 (12)	0.0267 (4)
C7	0.2869 (2)	0.1551 (2)	0.06884 (13)	0.0327 (5)
H7	0.2744	0.0866	0.1170	0.039*
C8	0.2398 (3)	0.0654 (3)	−0.01662 (16)	0.0514 (7)
H8A	0.1320	0.0322	−0.0273	0.062*
H8B	0.3069	−0.0241	−0.0125	0.062*
H8C	0.2504	0.1304	−0.0650	0.062*
C9	0.1804 (2)	0.2920 (2)	0.06525 (17)	0.0460 (6)
H9A	0.0736	0.2566	0.0564	0.055*
H9B	0.1867	0.3587	0.0167	0.055*
H9C	0.2125	0.3487	0.1204	0.055*
C10	0.8387 (2)	0.1508 (2)	0.26749 (14)	0.0349 (5)
H10	0.8116	0.0441	0.2800	0.042*
C11	1.0061 (2)	0.1496 (3)	0.26122 (17)	0.0505 (6)
H11A	1.0727	0.1026	0.3140	0.061*
H11B	1.0404	0.2545	0.2560	0.061*
H11C	1.0125	0.0909	0.2097	0.061*
C12	0.8260 (3)	0.2501 (3)	0.34482 (15)	0.0468 (6)
H12A	0.8939	0.2092	0.3991	0.056*
H12B	0.7187	0.2499	0.3488	0.056*
H12C	0.8573	0.3548	0.3360	0.056*
C13	0.4417 (2)	0.1082 (2)	0.28273 (13)	0.0309 (5)
H13	0.4131	0.0339	0.3192	0.037*

	U11	U22	U33	U12	U13	U23
N1	0.0361 (9)	0.0177 (7)	0.0303 (10)	−0.0005 (6)	0.0103 (8)	0.0028 (6)
O1	0.0492 (9)	0.0278 (7)	0.0443 (9)	−0.0025 (6)	0.0228 (7)	−0.0035 (6)
C1	0.0337 (11)	0.0167 (8)	0.0276 (11)	−0.0004 (7)	0.0120 (9)	0.0001 (7)
C2	0.0339 (11)	0.0187 (9)	0.0328 (12)	0.0019 (8)	0.0134 (9)	−0.0012 (7)
C3	0.0331 (11)	0.0229 (9)	0.0415 (13)	−0.0020 (8)	0.0171 (10)	−0.0035 (8)
C4	0.0464 (13)	0.0236 (9)	0.0354 (12)	0.0022 (9)	0.0240 (10)	0.0038 (8)
C5	0.0410 (12)	0.0272 (10)	0.0284 (11)	0.0044 (8)	0.0109 (9)	0.0027 (8)
C6	0.0348 (11)	0.0205 (9)	0.0270 (11)	0.0014 (8)	0.0120 (9)	−0.0018 (7)
C7	0.0339 (12)	0.0314 (10)	0.0312 (12)	−0.0015 (8)	0.0058 (9)	0.0026 (8)
C8	0.0455 (14)	0.0435 (13)	0.0606 (17)	−0.0008 (10)	0.0062 (12)	−0.0204 (11)
C9	0.0364 (13)	0.0465 (13)	0.0544 (16)	0.0002 (10)	0.0106 (11)	−0.0147 (11)
C10	0.0342 (12)	0.0284 (10)	0.0394 (13)	0.0004 (8)	0.0050 (10)	0.0049 (9)
C11	0.0374 (13)	0.0464 (13)	0.0636 (17)	0.0068 (10)	0.0065 (12)	0.0032 (11)
C12	0.0397 (13)	0.0600 (14)	0.0379 (14)	−0.0037 (11)	0.0052 (11)	−0.0007 (11)
C13	0.0361 (11)	0.0271 (10)	0.0305 (11)	−0.0062 (8)	0.0106 (9)	0.0022 (8)

N1—C13	1.331 (2)	C7—H7	1.0000
N1—C1	1.441 (2)	C8—H8A	0.9800
N1—H1	0.8800	C8—H8B	0.9800
O1—C13	1.229 (2)	C8—H8C	0.9800
C1—C6	1.401 (3)	C9—H9A	0.9800
C1—C2	1.402 (3)	C9—H9B	0.9800
C2—C3	1.397 (3)	C9—H9C	0.9800
C2—C10	1.522 (3)	C10—C11	1.529 (3)
C3—C4	1.382 (3)	C10—C12	1.532 (3)
C3—H3	0.9500	C10—H10	1.0000
C4—C5	1.377 (3)	C11—H11A	0.9800
C4—H4	0.9500	C11—H11B	0.9800
C5—C6	1.396 (3)	C11—H11C	0.9800
C5—H5	0.9500	C12—H12A	0.9800
C6—C7	1.520 (3)	C12—H12B	0.9800
C7—C9	1.525 (3)	C12—H12C	0.9800
C7—C8	1.525 (3)	C13—H13	0.9500
C13—N1—C1	123.23 (15)	C7—C8—H8C	109.5
C13—N1—H1	118.4	H8A—C8—H8C	109.5
C1—N1—H1	118.4	H8B—C8—H8C	109.5
C6—C1—C2	122.22 (17)	C7—C9—H9A	109.5
C6—C1—N1	119.19 (16)	C7—C9—H9B	109.5
C2—C1—N1	118.57 (17)	H9A—C9—H9B	109.5
C3—C2—C1	117.78 (18)	C7—C9—H9C	109.5
C3—C2—C10	121.42 (17)	H9A—C9—H9C	109.5
C1—C2—C10	120.80 (16)	H9B—C9—H9C	109.5
C4—C3—C2	120.77 (18)	C2—C10—C11	113.87 (18)
C4—C3—H3	119.6	C2—C10—C12	110.56 (16)
C2—C3—H3	119.6	C11—C10—C12	109.77 (18)
C5—C4—C3	120.46 (18)	C2—C10—H10	107.5
C5—C4—H4	119.8	C11—C10—H10	107.5
C3—C4—H4	119.8	C12—C10—H10	107.5
C4—C5—C6	121.17 (19)	C10—C11—H11A	109.5
C4—C5—H5	119.4	C10—C11—H11B	109.5
C6—C5—H5	119.4	H11A—C11—H11B	109.5
C5—C6—C1	117.59 (18)	C10—C11—H11C	109.5
C5—C6—C7	119.45 (17)	H11A—C11—H11C	109.5
C1—C6—C7	122.95 (16)	H11B—C11—H11C	109.5
C6—C7—C9	111.57 (15)	C10—C12—H12A	109.5
C6—C7—C8	111.09 (17)	C10—C12—H12B	109.5
C9—C7—C8	110.50 (18)	H12A—C12—H12B	109.5
C6—C7—H7	107.8	C10—C12—H12C	109.5
C9—C7—H7	107.8	H12A—C12—H12C	109.5
C8—C7—H7	107.8	H12B—C12—H12C	109.5
C7—C8—H8A	109.5	O1—C13—N1	125.92 (17)
C7—C8—H8B	109.5	O1—C13—H13	117.0
H8A—C8—H8B	109.5	N1—C13—H13	117.0
C13—N1—C1—C6	−77.0 (2)	N1—C1—C6—C5	−177.80 (15)
C13—N1—C1—C2	104.7 (2)	C2—C1—C6—C7	179.32 (16)
C6—C1—C2—C3	0.1 (3)	N1—C1—C6—C7	1.1 (3)
N1—C1—C2—C3	178.38 (15)	C5—C6—C7—C9	−64.7 (2)
C6—C1—C2—C10	179.73 (16)	C1—C6—C7—C9	116.4 (2)
N1—C1—C2—C10	−2.0 (2)	C5—C6—C7—C8	59.1 (2)
C1—C2—C3—C4	−0.5 (3)	C1—C6—C7—C8	−119.8 (2)
C10—C2—C3—C4	179.90 (17)	C3—C2—C10—C11	−24.2 (3)
C2—C3—C4—C5	0.3 (3)	C1—C2—C10—C11	156.20 (17)
C3—C4—C5—C6	0.3 (3)	C3—C2—C10—C12	99.9 (2)
C4—C5—C6—C1	−0.7 (3)	C1—C2—C10—C12	−79.7 (2)
C4—C5—C6—C7	−179.57 (17)	C1—N1—C13—O1	−2.2 (3)
C2—C1—C6—C5	0.4 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1i	0.88	2.04	2.910 (2)	171

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1i	0.88	2.04	2.910 (2)	171

Symmetry code: (i) .