2-(2,2-Dimethyl-2,3-dihydro-1-benzofuran-7-yl-oxy)-N-(o-tol-yl)acetamide.

In the title compound, C(19)H(21)NO(3), the dihedral angle between the mean planes of the two benzene rings is 38.13 (12)°. The furan ring adopts an envelope-like conformation with the C atom bonded to the dimethyl groups displaced by 0.356 (2) Å from the plane through the other four atoms. In the crystal, mol-ecules are linked into inversion dimers by weak C-H⋯O inter-molecular inter-actions.

Related literature

The title compound is a derivative of Carbofuran, a popular carbamate insecticide, see: Tomlin (1994 ▶). For related structures, see: Xu et al. (2005 ▶); Li et al. (2009 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C19H21NO3

M = 311.37

Monoclinic,

a = 9.0868 (18) Å

b = 8.9708 (18) Å

c = 20.230 (4) Å

β = 92.18 (3)°

V = 1647.9 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 293 K

0.32 × 0.28 × 0.21 mm

Data collection

Bruker APEXII area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.985, T max = 0.991

8246 measured reflections

2961 independent reflections

1649 reflections with I > 2σ(I)

R int = 0.047

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.130

S = 1.00

2961 reflections

211 parameters

H-atom parameters constrained

Δρmax = 0.16 e Å−3

Δρmin = −0.19 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: XP in SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810018672/jj2028sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810018672/jj2028Isup2.hkl

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

C19H21NO3	F(000) = 664
Mr = 311.37	Dx = 1.255 Mg m−3
Monoclinic, P21/n	Melting point: 363.75 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 9.0868 (18) Å	Cell parameters from 3600 reflections
b = 8.9708 (18) Å	θ = 1.4–28°
c = 20.230 (4) Å	µ = 0.09 mm−1
β = 92.18 (3)°	T = 293 K
V = 1647.9 (6) Å3	Block, colourless
Z = 4	0.32 × 0.28 × 0.21 mm

Bruker APEXII area-detector diffractometer	2961 independent reflections
Radiation source: fine-focus sealed tube	1649 reflections with I > 2σ(I)
graphite	Rint = 0.047
φ and ω scan	θmax = 25.2°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −8→10
Tmin = 0.985, Tmax = 0.991	k = −10→9
8246 measured reflections	l = −19→24

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: inferred from neighbouring sites
wR(F2) = 0.130	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.0561P)2] where P = (Fo2 + 2Fc2)/3
2961 reflections	(Δ/σ)max = 0.001
211 parameters	Δρmax = 0.16 e Å−3
0 restraints	Δρmin = −0.19 e Å−3

Experimental. 1H NMR in CDCl3 (300 MHz), delta: 1.49(s,6H,2CH3), 2.72(s,3H, ArCH3), 3.06(s,2H,CH2), 4.72 (s,2H, OCH2), 6.76~7.99(m,7H,C6H3,C6H4), 8.53(s,1H, NH). MS: 312.2(M+1)

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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
C7	0.4155 (3)	0.3064 (3)	0.23529 (11)	0.0590 (7)
H7A	0.3140	0.2780	0.2254	0.071*
H7B	0.4243	0.3430	0.2804	0.071*
C1	0.6148 (2)	0.4224 (2)	0.09104 (10)	0.0478 (6)
C2	0.5545 (2)	0.3488 (2)	0.14345 (10)	0.0452 (6)
C3	0.4665 (2)	0.4205 (3)	0.18741 (10)	0.0508 (6)
C6	0.5867 (3)	0.5737 (3)	0.08464 (11)	0.0625 (7)
H6	0.6271	0.6269	0.0503	0.075*
C8	0.5210 (3)	0.1749 (2)	0.22464 (10)	0.0534 (6)
C5	0.4988 (3)	0.6465 (3)	0.12900 (12)	0.0697 (7)
H5	0.4804	0.7479	0.1239	0.084*
C4	0.4384 (3)	0.5705 (3)	0.18046 (12)	0.0661 (7)
H4	0.3795	0.6198	0.2101	0.079*
C10	0.6543 (3)	0.1807 (3)	0.27130 (12)	0.0741 (8)
H10A	0.7220	0.1034	0.2601	0.111*
H10B	0.6243	0.1664	0.3159	0.111*
H10C	0.7014	0.2759	0.2677	0.111*
C9	0.4475 (3)	0.0248 (3)	0.22421 (12)	0.0761 (8)
H9A	0.3673	0.0243	0.1919	0.114*
H9B	0.4107	0.0046	0.2672	0.114*
H9C	0.5177	−0.0505	0.2133	0.114*
O1	0.57451 (16)	0.20069 (15)	0.15680 (7)	0.0515 (4)
O2	0.69720 (17)	0.34027 (15)	0.04836 (7)	0.0554 (5)
N1	0.83327 (19)	0.16952 (19)	−0.03274 (8)	0.0500 (5)
H1	0.7740	0.1490	−0.0019	0.060*
C11	0.8592 (3)	0.3146 (3)	−0.04218 (11)	0.0540 (6)
O3	0.9383 (2)	0.36591 (19)	−0.08343 (9)	0.0889 (7)
C12	0.7796 (3)	0.4201 (2)	0.00151 (11)	0.0569 (6)
H12A	0.8503	0.4844	0.0246	0.068*
H12B	0.7138	0.4823	−0.0254	0.068*
C13	0.8900 (3)	0.0448 (2)	−0.06653 (10)	0.0499 (6)
C14	0.8094 (3)	−0.0865 (3)	−0.06628 (11)	0.0611 (7)
C17	1.0776 (4)	−0.0718 (4)	−0.12804 (13)	0.0943 (11)
H17	1.1673	−0.0671	−0.1486	0.113*
C19	0.6654 (3)	−0.0952 (3)	−0.03299 (13)	0.0822 (8)
H19A	0.6813	−0.0796	0.0137	0.123*
H19B	0.6224	−0.1918	−0.0405	0.123*
H19C	0.6001	−0.0199	−0.0508	0.123*
C15	0.8674 (4)	−0.2095 (3)	−0.09801 (14)	0.0891 (10)
H15	0.8155	−0.2989	−0.0985	0.107*
C16	0.9987 (5)	−0.2025 (4)	−0.12855 (15)	0.1031 (13)
H16	1.0347	−0.2863	−0.1497	0.124*
C18	1.0232 (3)	0.0530 (3)	−0.09684 (10)	0.0664 (7)
H18	1.0761	0.1417	−0.0963	0.080*

	U11	U22	U33	U12	U13	U23
C7	0.0495 (15)	0.0799 (17)	0.0482 (14)	0.0056 (13)	0.0113 (11)	−0.0089 (12)
C1	0.0495 (14)	0.0487 (14)	0.0452 (13)	0.0017 (11)	0.0031 (11)	−0.0074 (10)
C2	0.0489 (14)	0.0448 (13)	0.0419 (13)	0.0012 (11)	0.0030 (11)	−0.0075 (10)
C3	0.0457 (14)	0.0594 (15)	0.0475 (14)	0.0022 (12)	0.0034 (11)	−0.0117 (11)
C6	0.0803 (19)	0.0517 (15)	0.0558 (15)	0.0002 (13)	0.0053 (14)	−0.0017 (11)
C8	0.0530 (15)	0.0674 (15)	0.0406 (13)	0.0041 (12)	0.0144 (11)	0.0004 (11)
C5	0.089 (2)	0.0528 (14)	0.0672 (17)	0.0128 (14)	0.0046 (15)	−0.0085 (13)
C4	0.0663 (18)	0.0676 (17)	0.0647 (17)	0.0142 (14)	0.0053 (14)	−0.0208 (13)
C10	0.0674 (18)	0.103 (2)	0.0522 (16)	0.0144 (15)	0.0057 (14)	0.0012 (14)
C9	0.090 (2)	0.0737 (18)	0.0664 (17)	−0.0086 (16)	0.0263 (15)	0.0080 (14)
O1	0.0605 (10)	0.0524 (9)	0.0426 (9)	0.0055 (8)	0.0167 (7)	−0.0009 (7)
O2	0.0686 (11)	0.0503 (9)	0.0489 (9)	0.0012 (8)	0.0242 (8)	0.0000 (7)
N1	0.0551 (12)	0.0523 (12)	0.0438 (11)	−0.0020 (9)	0.0175 (9)	0.0037 (8)
C11	0.0602 (16)	0.0583 (16)	0.0444 (14)	−0.0096 (12)	0.0129 (12)	0.0007 (11)
O3	0.1140 (16)	0.0713 (12)	0.0856 (13)	−0.0173 (11)	0.0584 (12)	0.0004 (9)
C12	0.0635 (16)	0.0550 (14)	0.0536 (14)	−0.0072 (12)	0.0190 (12)	−0.0003 (11)
C13	0.0599 (16)	0.0579 (15)	0.0319 (12)	0.0128 (12)	0.0023 (11)	0.0017 (10)
C14	0.0787 (19)	0.0548 (15)	0.0485 (14)	0.0045 (14)	−0.0137 (13)	−0.0024 (12)
C17	0.106 (3)	0.128 (3)	0.0505 (17)	0.059 (2)	0.0147 (17)	0.0032 (18)
C19	0.088 (2)	0.0724 (18)	0.085 (2)	−0.0193 (16)	−0.0079 (17)	0.0098 (15)
C15	0.134 (3)	0.0651 (19)	0.0653 (19)	0.020 (2)	−0.029 (2)	−0.0111 (15)
C16	0.149 (4)	0.100 (3)	0.058 (2)	0.063 (3)	−0.014 (2)	−0.0204 (19)
C18	0.0742 (18)	0.0837 (18)	0.0421 (14)	0.0215 (15)	0.0121 (13)	0.0088 (13)

C7—C3	1.495 (3)	C9—H9C	0.9600
C7—C8	1.540 (3)	O2—C12	1.423 (2)
C7—H7A	0.9700	N1—C11	1.337 (3)
C7—H7B	0.9700	N1—C13	1.418 (3)
C1—O2	1.378 (2)	N1—H1	0.8600
C1—C2	1.380 (3)	C11—O3	1.213 (2)
C1—C6	1.386 (3)	C11—C12	1.500 (3)
C2—O1	1.367 (2)	C12—H12A	0.9700
C2—C3	1.378 (3)	C12—H12B	0.9700
C3—C4	1.376 (3)	C13—C18	1.380 (3)
C6—C5	1.387 (3)	C13—C14	1.387 (3)
C6—H6	0.9300	C14—C15	1.390 (4)
C8—O1	1.492 (2)	C14—C19	1.497 (3)
C8—C9	1.503 (3)	C17—C16	1.374 (4)
C8—C10	1.508 (3)	C17—C18	1.386 (3)
C5—C4	1.376 (3)	C17—H17	0.9300
C5—H5	0.9300	C19—H19A	0.9600
C4—H4	0.9300	C19—H19B	0.9600
C10—H10A	0.9600	C19—H19C	0.9600
C10—H10B	0.9600	C15—C16	1.366 (4)
C10—H10C	0.9600	C15—H15	0.9300
C9—H9A	0.9600	C16—H16	0.9300
C9—H9B	0.9600	C18—H18	0.9300
C3—C7—C8	102.93 (17)	H9A—C9—H9C	109.5
C3—C7—H7A	111.2	H9B—C9—H9C	109.5
C8—C7—H7A	111.2	C2—O1—C8	106.68 (14)
C3—C7—H7B	111.2	C1—O2—C12	117.43 (16)
C8—C7—H7B	111.2	C11—N1—C13	129.02 (18)
H7A—C7—H7B	109.1	C11—N1—H1	115.5
O2—C1—C2	117.83 (18)	C13—N1—H1	115.5
O2—C1—C6	124.60 (19)	O3—C11—N1	125.5 (2)
C2—C1—C6	117.56 (19)	O3—C11—C12	118.5 (2)
O1—C2—C3	113.71 (19)	N1—C11—C12	116.00 (18)
O1—C2—C1	124.27 (18)	O2—C12—C11	110.67 (18)
C3—C2—C1	122.0 (2)	O2—C12—H12A	109.5
C4—C3—C2	120.0 (2)	C11—C12—H12A	109.5
C4—C3—C7	132.5 (2)	O2—C12—H12B	109.5
C2—C3—C7	107.51 (19)	C11—C12—H12B	109.5
C1—C6—C5	120.6 (2)	H12A—C12—H12B	108.1
C1—C6—H6	119.7	C18—C13—C14	121.3 (2)
C5—C6—H6	119.7	C18—C13—N1	120.9 (2)
O1—C8—C9	107.10 (17)	C14—C13—N1	117.8 (2)
O1—C8—C10	106.75 (18)	C13—C14—C15	117.6 (3)
C9—C8—C10	112.3 (2)	C13—C14—C19	121.1 (2)
O1—C8—C7	103.68 (16)	C15—C14—C19	121.3 (3)
C9—C8—C7	114.1 (2)	C16—C17—C18	119.9 (3)
C10—C8—C7	112.06 (19)	C16—C17—H17	120.1
C4—C5—C6	120.8 (2)	C18—C17—H17	120.1
C4—C5—H5	119.6	C14—C19—H19A	109.5
C6—C5—H5	119.6	C14—C19—H19B	109.5
C5—C4—C3	119.0 (2)	H19A—C19—H19B	109.5
C5—C4—H4	120.5	C14—C19—H19C	109.5
C3—C4—H4	120.5	H19A—C19—H19C	109.5
C8—C10—H10A	109.5	H19B—C19—H19C	109.5
C8—C10—H10B	109.5	C16—C15—C14	121.7 (3)
H10A—C10—H10B	109.5	C16—C15—H15	119.2
C8—C10—H10C	109.5	C14—C15—H15	119.2
H10A—C10—H10C	109.5	C15—C16—C17	120.0 (3)
H10B—C10—H10C	109.5	C15—C16—H16	120.0
C8—C9—H9A	109.5	C17—C16—H16	120.0
C8—C9—H9B	109.5	C13—C18—C17	119.6 (3)
H9A—C9—H9B	109.5	C13—C18—H18	120.2
C8—C9—H9C	109.5	C17—C18—H18	120.2

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12A···O3i	0.97	2.60	3.561 (3)	174

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C12—H12A⋯O3i	0.97	2.60	3.561 (3)	174

Symmetry code: (i) .