N-(2,6-Diisopropyl-phen-yl)formamide toluene 0.33-solvate.

The crystal packing of the title compound, C(13)H(19)NO·0.33C(7)H(8), shows a channel at [001], which contains grossly disordered toluene solvent mol-ecules. The angle between the benzene ring and the mean plane of the formamide group is 71.1 (1)°. The amide groups of neighbouring mol-ecules are connected by N-H⋯O hydrogen bonds, forming 2(1) helical chains propagating along [001]. Mol-ecules are also connected by weak inter-molecular C-H⋯O hydrogen bonds, forming 6(1) helices.

Related literature

For the synthesis of the starting material, see: Krishnamurthy (1982 ▶); Hinter­mann (2007 ▶). For the crystal structures of related compounds, see: Stibrany & Potenza (2006 ▶); Chitanda et al. (2008 ▶); Omondi et al. (2008 ▶); Gowda et al. (2009 ▶). For the treatment of the disordered solvent, see: Spek (2009 ▶).

Experimental

Crystal data

C13H19NO·0.33C7H8

M = 236.00

Hexagonal,

a = 16.9133 (6) Å

c = 8.4451 (4) Å

V = 2092.2 (2) Å3

Z = 6

Mo Kα radiation

μ = 0.07 mm−1

T = 185 K

0.65 × 0.20 × 0.19 mm

Data collection

Siemens SMART 1K CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2000 ▶) T min = 0.933, T max = 0.987

23771 measured reflections

1748 independent reflections

1503 reflections with I > 2σ(I)

R int = 0.057

Refinement

R[F 2 > 2σ(F 2)] = 0.058

wR(F 2) = 0.125

S = 1.08

1748 reflections

144 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.16 e Å−3

Δρmin = −0.16 e Å−3

Data collection: SMART (Siemens, 1995 ▶); cell refinement: SAINT (Siemens, 1995 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812017527/su2409sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812017527/su2409Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812017527/su2409Isup3.cml

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

C13H19NO·0.33C7H8	Dx = 1.124 Mg m−3
Mr = 236.00	Mo Kα radiation, λ = 0.71073 Å
Hexagonal, P61	Cell parameters from 8192 reflections
Hall symbol: P 61	θ = 3–24°
a = 16.9133 (6) Å	µ = 0.07 mm−1
c = 8.4451 (4) Å	T = 185 K
V = 2092.2 (2) Å3	Rod, colourless
Z = 6	0.65 × 0.20 × 0.19 mm
F(000) = 772

Siemens SMART 1K CCD diffractometer	1748 independent reflections
Radiation source: normal-focus sealed tube	1503 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.057
ω scans	θmax = 28.0°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 2000)	h = −21→21
Tmin = 0.933, Tmax = 0.987	k = −22→21
23771 measured reflections	l = −11→10

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)] = 0.058	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.125	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	w = 1/[σ2(Fo2) + (0.06P)2 + 0.4P] where P = (Fo2 + 2Fc2)/3
1748 reflections	(Δ/σ)max < 0.001
144 parameters	Δρmax = 0.16 e Å−3
1 restraint	Δρmin = −0.16 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
O1	0.08661 (11)	0.55915 (13)	0.1114 (2)	0.0375 (5)
N1	−0.02094 (15)	0.50925 (15)	0.3050 (3)	0.0315 (5)
H1A	−0.0291 (19)	0.496 (2)	0.397 (4)	0.034 (8)*
C1	−0.09762 (16)	0.49482 (18)	0.2086 (3)	0.0297 (6)
C2	−0.16677 (16)	0.40479 (18)	0.1800 (3)	0.0323 (6)
C3	−0.24197 (17)	0.3921 (2)	0.0909 (3)	0.0410 (7)
H3A	−0.2899	0.3320	0.0689	0.049*
C4	−0.24742 (19)	0.4656 (2)	0.0349 (4)	0.0464 (8)
H4A	−0.2995	0.4556	−0.0238	0.056*
C5	−0.17845 (19)	0.5530 (2)	0.0628 (4)	0.0458 (7)
H5A	−0.1830	0.6028	0.0212	0.055*
C6	−0.10153 (17)	0.57032 (19)	0.1513 (3)	0.0375 (6)
C7	−0.15810 (18)	0.32460 (18)	0.2384 (3)	0.0387 (6)
H7A	−0.1271	0.3417	0.3438	0.046*
C8	−0.2497 (2)	0.2370 (2)	0.2604 (4)	0.0532 (8)
H8A	−0.2893	0.2495	0.3281	0.080*
H8B	−0.2398	0.1904	0.3103	0.080*
H8C	−0.2789	0.2150	0.1570	0.080*
C9	−0.0972 (2)	0.3076 (2)	0.1255 (4)	0.0480 (8)
H9A	−0.0378	0.3636	0.1155	0.072*
H9B	−0.1263	0.2900	0.0212	0.072*
H9C	−0.0884	0.2585	0.1676	0.072*
C10	−0.02693 (19)	0.6683 (2)	0.1845 (4)	0.0443 (7)
H10A	0.0267	0.6660	0.2289	0.053*
C11	−0.0572 (3)	0.7136 (2)	0.3082 (6)	0.0721 (11)
H11A	−0.0756	0.6768	0.4052	0.108*
H11B	−0.1090	0.7181	0.2670	0.108*
H11C	−0.0065	0.7748	0.3317	0.108*
C12	0.0049 (3)	0.7257 (3)	0.0336 (6)	0.0755 (12)
H12A	0.0159	0.6919	−0.0494	0.113*
H12B	0.0615	0.7830	0.0551	0.113*
H12C	−0.0423	0.7392	−0.0018	0.113*
C13	0.06249 (17)	0.53788 (17)	0.2494 (3)	0.0319 (6)
H13A	0.1072	0.5423	0.3224	0.038*

	U11	U22	U33	U12	U13	U23
O1	0.0290 (9)	0.0517 (11)	0.0258 (10)	0.0156 (9)	−0.0015 (8)	−0.0027 (8)
N1	0.0328 (12)	0.0378 (12)	0.0192 (11)	0.0141 (10)	−0.0025 (9)	−0.0013 (10)
C1	0.0236 (12)	0.0416 (14)	0.0241 (13)	0.0166 (10)	0.0014 (10)	−0.0033 (11)
C2	0.0269 (12)	0.0433 (14)	0.0218 (12)	0.0138 (11)	0.0042 (10)	−0.0044 (11)
C3	0.0291 (13)	0.0561 (17)	0.0313 (15)	0.0163 (13)	−0.0002 (12)	−0.0094 (14)
C4	0.0287 (14)	0.075 (2)	0.0391 (16)	0.0288 (15)	−0.0051 (12)	−0.0067 (15)
C5	0.0412 (16)	0.0625 (18)	0.0452 (18)	0.0345 (15)	0.0027 (14)	0.0055 (15)
C6	0.0311 (13)	0.0508 (16)	0.0337 (15)	0.0227 (12)	0.0050 (11)	0.0009 (13)
C7	0.0377 (14)	0.0409 (15)	0.0301 (14)	0.0141 (12)	−0.0028 (12)	−0.0046 (12)
C8	0.0514 (18)	0.0426 (16)	0.0497 (18)	0.0117 (14)	0.0077 (16)	−0.0040 (15)
C9	0.0461 (16)	0.0455 (16)	0.0511 (19)	0.0219 (13)	0.0010 (15)	−0.0035 (15)
C10	0.0391 (15)	0.0446 (16)	0.0546 (19)	0.0250 (13)	0.0054 (14)	0.0076 (15)
C11	0.064 (2)	0.0493 (18)	0.082 (3)	0.0127 (16)	0.012 (2)	−0.016 (2)
C12	0.073 (2)	0.066 (2)	0.077 (3)	0.026 (2)	0.022 (2)	0.023 (2)
C13	0.0275 (12)	0.0368 (14)	0.0280 (13)	0.0134 (11)	−0.0070 (10)	−0.0054 (11)

O1—C13	1.227 (3)	C7—H7A	1.0000
N1—C13	1.328 (4)	C8—H8A	0.9800
N1—C1	1.445 (3)	C8—H8B	0.9800
N1—H1A	0.80 (4)	C8—H8C	0.9800
C1—C6	1.398 (4)	C9—H9A	0.9800
C1—C2	1.401 (4)	C9—H9B	0.9800
C2—C3	1.399 (4)	C9—H9C	0.9800
C2—C7	1.517 (4)	C10—C11	1.527 (5)
C3—C4	1.375 (4)	C10—C12	1.528 (5)
C3—H3A	0.9500	C10—H10A	1.0000
C4—C5	1.371 (4)	C11—H11A	0.9800
C4—H4A	0.9500	C11—H11B	0.9800
C5—C6	1.399 (4)	C11—H11C	0.9800
C5—H5A	0.9500	C12—H12A	0.9800
C6—C10	1.525 (4)	C12—H12B	0.9800
C7—C8	1.528 (4)	C12—H12C	0.9800
C7—C9	1.532 (4)	C13—H13A	0.9500
C13—N1—C1	124.2 (2)	C7—C8—H8C	109.5
C13—N1—H1A	117 (2)	H8A—C8—H8C	109.5
C1—N1—H1A	119 (2)	H8B—C8—H8C	109.5
C6—C1—C2	122.6 (2)	C7—C9—H9A	109.5
C6—C1—N1	119.3 (2)	C7—C9—H9B	109.5
C2—C1—N1	118.1 (2)	H9A—C9—H9B	109.5
C3—C2—C1	117.4 (2)	C7—C9—H9C	109.5
C3—C2—C7	121.6 (2)	H9A—C9—H9C	109.5
C1—C2—C7	120.9 (2)	H9B—C9—H9C	109.5
C4—C3—C2	120.9 (3)	C6—C10—C11	111.6 (2)
C4—C3—H3A	119.6	C6—C10—C12	112.0 (3)
C2—C3—H3A	119.6	C11—C10—C12	110.6 (3)
C5—C4—C3	120.7 (3)	C6—C10—H10A	107.5
C5—C4—H4A	119.7	C11—C10—H10A	107.5
C3—C4—H4A	119.7	C12—C10—H10A	107.5
C4—C5—C6	121.2 (3)	C10—C11—H11A	109.5
C4—C5—H5A	119.4	C10—C11—H11B	109.5
C6—C5—H5A	119.4	H11A—C11—H11B	109.5
C1—C6—C5	117.2 (3)	C10—C11—H11C	109.5
C1—C6—C10	122.5 (2)	H11A—C11—H11C	109.5
C5—C6—C10	120.2 (3)	H11B—C11—H11C	109.5
C2—C7—C8	113.7 (2)	C10—C12—H12A	109.5
C2—C7—C9	109.9 (2)	C10—C12—H12B	109.5
C8—C7—C9	110.2 (2)	H12A—C12—H12B	109.5
C2—C7—H7A	107.6	C10—C12—H12C	109.5
C8—C7—H7A	107.6	H12A—C12—H12C	109.5
C9—C7—H7A	107.6	H12B—C12—H12C	109.5
C7—C8—H8A	109.5	O1—C13—N1	125.4 (2)
C7—C8—H8B	109.5	O1—C13—H13A	117.3
H8A—C8—H8B	109.5	N1—C13—H13A	117.3
C13—N1—C1—C6	−73.6 (3)	N1—C1—C6—C10	0.9 (4)
C13—N1—C1—C2	108.2 (3)	C4—C5—C6—C1	0.6 (4)
C6—C1—C2—C3	−0.3 (4)	C4—C5—C6—C10	−178.3 (3)
N1—C1—C2—C3	177.9 (2)	C3—C2—C7—C8	−26.6 (4)
C6—C1—C2—C7	177.4 (2)	C1—C2—C7—C8	155.8 (2)
N1—C1—C2—C7	−4.4 (3)	C3—C2—C7—C9	97.4 (3)
C1—C2—C3—C4	−0.3 (4)	C1—C2—C7—C9	−80.1 (3)
C7—C2—C3—C4	−178.0 (3)	C1—C6—C10—C11	−105.1 (3)
C2—C3—C4—C5	1.1 (4)	C5—C6—C10—C11	73.8 (4)
C3—C4—C5—C6	−1.2 (5)	C1—C6—C10—C12	130.3 (3)
C2—C1—C6—C5	0.2 (4)	C5—C6—C10—C12	−50.8 (4)
N1—C1—C6—C5	−178.0 (2)	C1—N1—C13—O1	3.0 (4)
C2—C1—C6—C10	179.1 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1i	0.80 (4)	2.05 (4)	2.826 (3)	164 (3)
C4—H4A···O1ii	0.95	2.56	3.418 (3)	150
C13—H13A···C3i	0.95	3.01	3.917 (4)	161
C13—H13A···C4i	0.95	3.03	3.973 (4)	173

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O1i	0.80 (4)	2.05 (4)	2.826 (3)	164 (3)
C4—H4A⋯O1ii	0.95	2.56	3.418 (3)	150
C13—H13A⋯C3i	0.95	3.01	3.917 (4)	161
C13—H13A⋯C4i	0.95	3.03	3.973 (4)	173

Symmetry codes: (i) ; (ii) .