2-Isopropoxyphenyl N-methyl-carbamate.

In the title compound, C(11)H(15)NO(3), the mean planes of the carboxamide and isopropyl groups are inclined at 109.9 (1) and 128.7 (2)°, respectively, to the mean plane of the phen-oxy group. In the crystal structure, mol-ecules are stacked along the b axis, without any π-π inter-actions. The stacked columns are linked together by inter-molecular N-H⋯O hydrogen bonds, with an N⋯O distance of 2.842 (2) Å.

Related literature

For background literature, see: Abburi & Nutalapati (2004 ▶); Moreno et al. (2001 ▶); Wang et al. (1998 ▶). For a report of a similar compound, see: Czugler & Kalman (1975 ▶).

Experimental

Crystal data

C11H15NO3

M = 209.24

Monoclinic,

a = 13.275 (3) Å

b = 8.8890 (18) Å

c = 9.931 (2) Å

β = 90.59 (3)°

V = 1171.8 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 293 (2) K

0.30 × 0.10 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: ψ scan (CAD-4 Software; Enraf–Nonius, 1989 ▶) T min = 0.975, T max = 0.991

2257 measured reflections

2121 independent reflections

1255 reflections with I > 2σ(I)

R int = 0.023

3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F 2 > 2σ(F 2)] = 0.060

wR(F 2) = 0.152

S = 1.01

2121 reflections

136 parameters

H-atom parameters constrained

Δρmax = 0.21 e Å−3

Δρmin = −0.16 e Å−3

Data collection: CAD-4 Software (Enraf–Nonius, 1989 ▶); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995 ▶); 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: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809002372/pv2125sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809002372/pv2125Isup2.hkl

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

C11H15NO3	F(000) = 448
Mr = 209.24	Dx = 1.186 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 25 reflections
a = 13.275 (3) Å	θ = 9–12°
b = 8.8890 (18) Å	µ = 0.09 mm−1
c = 9.931 (2) Å	T = 293 K
β = 90.59 (3)°	Needle, colourless
V = 1171.8 (4) Å3	0.30 × 0.10 × 0.10 mm
Z = 4

Enraf–Nonius CAD-4 diffractometer	1255 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.023
graphite	θmax = 25.3°, θmin = 1.5°
ω/2θ scans	h = −15→15
Absorption correction: ψ scan (CAD-4 Software; Enraf–Nonius, 1989)	k = 0→10
Tmin = 0.975, Tmax = 0.991	l = 0→11
2257 measured reflections	3 standard reflections every 200 reflections
2121 independent reflections	intensity decay: 1%

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.060	H-atom parameters constrained
wR(F2) = 0.152	w = 1/[σ2(Fo2) + (0.06P)2 + 0.55P] where P = (Fo2 + 2Fc2)/3
S = 1.01	(Δ/σ)max < 0.001
2121 reflections	Δρmax = 0.21 e Å−3
136 parameters	Δρmin = −0.16 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008)
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 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	0.60393 (17)	0.3161 (3)	−0.19856 (18)	0.0506 (6)
H0A	0.6177	0.2831	−0.2777	0.061*
O1	0.82141 (16)	0.1745 (2)	0.0186 (2)	0.0748 (7)
O2	0.66395 (14)	0.0939 (2)	−0.13306 (16)	0.0526 (5)
O3	0.60236 (15)	0.2566 (2)	0.02273 (15)	0.0566 (6)
C1	0.8569 (3)	0.4130 (4)	0.1055 (4)	0.0941 (12)
H1A	0.7868	0.4283	0.1236	0.141*
H1B	0.8712	0.4451	0.0154	0.141*
H1C	0.8968	0.4705	0.1682	0.141*
C2	0.9872 (3)	0.2104 (4)	0.1067 (4)	0.0874 (11)
H2A	0.9973	0.1079	0.1341	0.131*
H2B	1.0274	0.2756	0.1625	0.131*
H2C	1.0067	0.2218	0.0144	0.131*
C3	0.8819 (3)	0.2495 (4)	0.1202 (4)	0.0884 (12)
H3A	0.8594	0.2159	0.2089	0.106*
C4	0.7804 (2)	0.0381 (3)	0.0493 (3)	0.0497 (7)
C5	0.6971 (2)	−0.0015 (3)	−0.0310 (2)	0.0448 (7)
C6	0.6512 (2)	−0.1395 (4)	−0.0155 (3)	0.0587 (8)
H6A	0.5964	−0.1656	−0.0696	0.070*
C7	0.6867 (3)	−0.2379 (4)	0.0800 (3)	0.0692 (9)
H7A	0.6564	−0.3316	0.0899	0.083*
C8	0.7652 (3)	−0.1993 (4)	0.1594 (4)	0.0707 (9)
H8A	0.7882	−0.2667	0.2244	0.085*
C9	0.8130 (2)	−0.0602 (3)	0.1463 (3)	0.0668 (9)
H9A	0.8664	−0.0347	0.2030	0.080*
C10	0.62194 (18)	0.2312 (3)	−0.0929 (2)	0.0386 (6)
C11	0.5614 (2)	0.4638 (3)	−0.1832 (3)	0.0588 (8)
H11A	0.5510	0.5082	−0.2704	0.088*
H11B	0.6067	0.5254	−0.1313	0.088*
H11C	0.4981	0.4564	−0.1378	0.088*

	U11	U22	U33	U12	U13	U23
N1	0.0653 (15)	0.0723 (17)	0.0143 (9)	−0.0010 (13)	0.0002 (9)	−0.0007 (9)
O1	0.0689 (15)	0.0644 (14)	0.0905 (15)	−0.0241 (12)	−0.0349 (12)	0.0110 (12)
O2	0.0634 (13)	0.0637 (13)	0.0305 (9)	0.0012 (10)	−0.0072 (8)	−0.0068 (9)
O3	0.0708 (14)	0.0784 (14)	0.0206 (9)	0.0144 (11)	−0.0055 (8)	−0.0029 (9)
C1	0.103 (3)	0.081 (3)	0.097 (3)	−0.006 (2)	0.004 (2)	−0.004 (2)
C2	0.076 (3)	0.095 (3)	0.090 (3)	−0.004 (2)	0.001 (2)	−0.001 (2)
C3	0.080 (3)	0.066 (2)	0.119 (3)	−0.022 (2)	−0.028 (2)	−0.016 (2)
C4	0.0456 (16)	0.0444 (17)	0.0590 (17)	−0.0041 (14)	−0.0059 (13)	0.0040 (13)
C5	0.0429 (15)	0.0550 (18)	0.0365 (13)	−0.0029 (14)	−0.0024 (12)	−0.0027 (12)
C6	0.0532 (19)	0.064 (2)	0.0585 (18)	−0.0117 (16)	−0.0025 (14)	−0.0144 (16)
C7	0.070 (2)	0.0504 (19)	0.087 (2)	−0.0091 (17)	0.0016 (19)	−0.0051 (18)
C8	0.071 (2)	0.057 (2)	0.084 (2)	0.0083 (18)	−0.0022 (18)	0.0126 (17)
C9	0.056 (2)	0.055 (2)	0.088 (2)	0.0049 (16)	−0.0258 (17)	0.0023 (17)
C10	0.0387 (14)	0.0598 (17)	0.0171 (11)	−0.0121 (13)	−0.0076 (9)	0.0017 (11)
C11	0.066 (2)	0.069 (2)	0.0413 (15)	0.0057 (17)	−0.0028 (14)	0.0027 (14)

N1—C10	1.313 (3)	C2—H2C	0.9600
N1—C11	1.438 (4)	C3—H3A	0.9800
N1—H0A	0.8600	C4—C9	1.368 (4)
O1—C4	1.365 (3)	C4—C5	1.402 (4)
O1—C3	1.446 (4)	C5—C6	1.379 (4)
O2—C5	1.390 (3)	C6—C7	1.370 (4)
O2—C10	1.401 (3)	C6—H6A	0.9300
O3—C10	1.201 (3)	C7—C8	1.346 (4)
C1—C3	1.498 (5)	C7—H7A	0.9300
C1—H1A	0.9600	C8—C9	1.395 (4)
C1—H1B	0.9600	C8—H8A	0.9300
C1—H1C	0.9600	C9—H9A	0.9300
C2—C3	1.448 (5)	C11—H11A	0.9600
C2—H2A	0.9600	C11—H11B	0.9600
C2—H2B	0.9600	C11—H11C	0.9600
C10—N1—C11	120.6 (2)	C9—C4—C5	118.8 (3)
C10—N1—H0A	119.7	C6—C5—O2	119.2 (2)
C11—N1—H0A	119.7	C6—C5—C4	120.5 (3)
C4—O1—C3	118.3 (2)	O2—C5—C4	120.2 (2)
C5—O2—C10	116.62 (17)	C7—C6—C5	119.8 (3)
C3—C1—H1A	109.5	C7—C6—H6A	120.1
C3—C1—H1B	109.5	C5—C6—H6A	120.1
H1A—C1—H1B	109.5	C8—C7—C6	120.1 (3)
C3—C1—H1C	109.5	C8—C7—H7A	120.0
H1A—C1—H1C	109.5	C6—C7—H7A	120.0
H1B—C1—H1C	109.5	C7—C8—C9	121.4 (3)
C3—C2—H2A	109.5	C7—C8—H8A	119.3
C3—C2—H2B	109.5	C9—C8—H8A	119.3
H2A—C2—H2B	109.5	C4—C9—C8	119.4 (3)
C3—C2—H2C	109.5	C4—C9—H9A	120.3
H2A—C2—H2C	109.5	C8—C9—H9A	120.3
H2B—C2—H2C	109.5	O3—C10—N1	128.1 (3)
O1—C3—C2	110.8 (3)	O3—C10—O2	121.8 (2)
O1—C3—C1	105.0 (3)	N1—C10—O2	110.05 (19)
C2—C3—C1	115.9 (3)	N1—C11—H11A	109.5
O1—C3—H3A	108.3	N1—C11—H11B	109.5
C2—C3—H3A	108.3	H11A—C11—H11B	109.5
C1—C3—H3A	108.3	N1—C11—H11C	109.5
O1—C4—C9	127.0 (3)	H11A—C11—H11C	109.5
O1—C4—C5	114.2 (2)	H11B—C11—H11C	109.5
C4—O1—C3—C2	91.9 (4)	C4—C5—C6—C7	0.6 (4)
C4—O1—C3—C1	−142.3 (3)	C5—C6—C7—C8	0.9 (5)
C3—O1—C4—C9	−22.3 (5)	C6—C7—C8—C9	−0.6 (5)
C3—O1—C4—C5	158.6 (3)	O1—C4—C9—C8	−176.6 (3)
C10—O2—C5—C6	116.3 (3)	C5—C4—C9—C8	2.5 (5)
C10—O2—C5—C4	−67.7 (3)	C7—C8—C9—C4	−1.1 (5)
O1—C4—C5—C6	176.9 (2)	C11—N1—C10—O3	4.4 (4)
C9—C4—C5—C6	−2.3 (4)	C11—N1—C10—O2	−179.5 (2)
O1—C4—C5—O2	1.0 (4)	C5—O2—C10—O3	−10.2 (3)
C9—C4—C5—O2	−178.1 (3)	C5—O2—C10—N1	173.3 (2)
O2—C5—C6—C7	176.5 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H0A···O3i	0.86	2.02	2.842 (2)	159

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H0A⋯O3i	0.86	2.02	2.842 (2)	159

Symmetry code: (i) .