2,2-Dimethyl-1,3-benzodioxol-4-yl N-methyl-carbamate.

In the title compound, C(11)H(13)NO(4), the two fused rings are almost coplanar, making a dihedral angle of 3.02 (8)°. In the crystal, chains are formed parallel to [010] through N-H⋯O hydrogen bonds between the amine and carbonyl groups.

Related literature

For benzodioxole derivatives, see: Ullrich et al. (2004 ▶); Gates & Gillon (1974 ▶); Arndt & Franke (1977 ▶); Joshi et al. (2005 ▶); Jae et al. (2001 ▶); Leite et al. (2004 ▶).

Experimental

Crystal data

C11H13NO4

M = 223.22

Monoclinic,

a = 9.505 (6) Å

b = 9.669 (7) Å

c = 12.355 (8) Å

β = 94.326 (11)°

V = 1132.2 (13) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 298 K

0.24 × 0.18 × 0.16 mm

Data collection

Siemens SMART APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Siemens, 1996 ▶) T min = 0.976, T max = 0.984

5692 measured reflections

2003 independent reflections

1615 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.098

S = 1.03

2003 reflections

146 parameters

H-atom parameters constrained

Δρmax = 0.19 e Å−3

Δρmin = −0.13 e Å−3

Data collection: SMART (Siemens, 1996 ▶); cell refinement: SAINT (Siemens, 1996 ▶); 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: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810036123/bh2301sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810036123/bh2301Isup2.hkl

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

C11H13NO4	F(000) = 472
Mr = 223.22	Dx = 1.310 Mg m−3
Monoclinic, P21/n	Melting point: 408 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 9.505 (6) Å	Cell parameters from 2406 reflections
b = 9.669 (7) Å	θ = 2.7–26.7°
c = 12.355 (8) Å	µ = 0.10 mm−1
β = 94.326 (11)°	T = 298 K
V = 1132.2 (13) Å3	Block, colorless
Z = 4	0.24 × 0.18 × 0.16 mm

Siemens SMART APEX CCD area-detector diffractometer	2003 independent reflections
Radiation source: fine-focus sealed tube	1615 reflections with I > 2σ(I)
graphite	Rint = 0.023
φ and ω scans	θmax = 25.1°, θmin = 2.7°
Absorption correction: multi-scan (SADABS; Siemens, 1996)	h = −11→10
Tmin = 0.976, Tmax = 0.984	k = −11→11
5692 measured reflections	l = −13→14

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)] = 0.035	H-atom parameters constrained
wR(F2) = 0.098	w = 1/[σ2(Fo2) + (0.0465P)2 + 0.1766P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max < 0.001
2003 reflections	Δρmax = 0.19 e Å−3
146 parameters	Δρmin = −0.13 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 constraints	Extinction coefficient: 0.035 (3)
Primary atom site location: structure-invariant direct methods

	x	y	z	Uiso*/Ueq
O1	0.78908 (12)	0.22049 (10)	0.73401 (10)	0.0666 (3)
O2	0.91170 (11)	0.04289 (10)	0.81309 (9)	0.0614 (3)
O3	1.07164 (11)	0.14292 (11)	0.63309 (8)	0.0624 (3)
O4	1.27901 (11)	0.26676 (13)	0.65853 (9)	0.0707 (4)
N1	0.69122 (14)	0.01063 (12)	0.74902 (10)	0.0589 (4)
H1	0.7052	−0.0723	0.7726	0.071*
C1	0.55627 (18)	0.04608 (19)	0.69670 (16)	0.0748 (5)
H1A	0.5096	0.1103	0.7412	0.112*
H1B	0.4999	−0.0360	0.6864	0.112*
H1C	0.5689	0.0876	0.6275	0.112*
C2	0.79399 (16)	0.10118 (14)	0.76185 (11)	0.0491 (4)
C3	1.03134 (16)	0.12582 (15)	0.82661 (12)	0.0537 (4)
C4	1.10295 (15)	0.16741 (14)	0.74063 (11)	0.0505 (4)
C5	1.22535 (16)	0.24235 (16)	0.75644 (12)	0.0554 (4)
C6	1.28072 (19)	0.27957 (18)	0.85695 (14)	0.0674 (5)
H6	1.3632	0.3313	0.8667	0.081*
C7	1.2084 (2)	0.23669 (19)	0.94372 (14)	0.0730 (5)
H7	1.2435	0.2597	1.0137	0.088*
C8	1.0863 (2)	0.16103 (17)	0.92966 (13)	0.0670 (5)
H8	1.0402	0.1333	0.9898	0.080*
C9	1.17105 (17)	0.22577 (17)	0.57665 (13)	0.0602 (4)
C10	1.2336 (2)	0.1358 (2)	0.49544 (16)	0.0884 (6)
H10A	1.3010	0.1879	0.4581	0.133*
H10B	1.1604	0.1029	0.4441	0.133*
H10C	1.2798	0.0586	0.5316	0.133*
C11	1.0989 (2)	0.35311 (19)	0.53297 (16)	0.0795 (5)
H11A	1.0580	0.4014	0.5908	0.119*
H11B	1.0260	0.3280	0.4785	0.119*
H11C	1.1662	0.4119	0.5015	0.119*

	U11	U22	U33	U12	U13	U23
O1	0.0786 (8)	0.0347 (6)	0.0860 (8)	0.0026 (5)	0.0022 (6)	0.0060 (5)
O2	0.0715 (7)	0.0454 (6)	0.0679 (7)	0.0011 (5)	0.0085 (5)	0.0166 (5)
O3	0.0668 (7)	0.0740 (7)	0.0466 (6)	−0.0115 (5)	0.0049 (5)	−0.0029 (5)
O4	0.0564 (6)	0.0921 (9)	0.0635 (7)	−0.0089 (6)	0.0032 (5)	0.0079 (6)
N1	0.0698 (8)	0.0357 (6)	0.0725 (9)	−0.0011 (6)	0.0139 (7)	0.0037 (6)
C1	0.0679 (11)	0.0654 (11)	0.0919 (13)	−0.0016 (9)	0.0109 (10)	0.0018 (9)
C2	0.0669 (9)	0.0353 (7)	0.0470 (8)	0.0064 (7)	0.0154 (7)	−0.0002 (6)
C3	0.0642 (9)	0.0450 (8)	0.0520 (9)	0.0082 (7)	0.0046 (7)	0.0053 (6)
C4	0.0594 (9)	0.0461 (8)	0.0454 (8)	0.0054 (7)	0.0009 (7)	−0.0001 (6)
C5	0.0547 (9)	0.0559 (8)	0.0547 (9)	0.0069 (7)	−0.0012 (7)	0.0018 (7)
C6	0.0635 (10)	0.0667 (11)	0.0695 (11)	0.0067 (8)	−0.0119 (9)	−0.0060 (8)
C7	0.0874 (13)	0.0752 (11)	0.0536 (10)	0.0159 (10)	−0.0133 (9)	−0.0085 (8)
C8	0.0877 (12)	0.0655 (10)	0.0479 (9)	0.0156 (9)	0.0055 (8)	0.0062 (7)
C9	0.0618 (9)	0.0676 (10)	0.0516 (9)	−0.0041 (8)	0.0069 (7)	0.0054 (7)
C10	0.1012 (15)	0.0889 (14)	0.0794 (13)	−0.0004 (11)	0.0356 (11)	−0.0040 (10)
C11	0.0805 (12)	0.0732 (12)	0.0827 (13)	0.0011 (10)	−0.0081 (10)	0.0106 (9)

O1—C2	1.2037 (18)	C4—C5	1.372 (2)
O2—C2	1.3650 (18)	C5—C6	1.360 (2)
O2—C3	1.3911 (19)	C6—C7	1.380 (3)
O3—C4	1.3603 (19)	C6—H6	0.9300
O3—C9	1.4560 (19)	C7—C8	1.372 (3)
O4—C5	1.368 (2)	C7—H7	0.9300
O4—C9	1.441 (2)	C8—H8	0.9300
N1—C2	1.312 (2)	C9—C10	1.485 (2)
N1—C1	1.434 (2)	C9—C11	1.490 (2)
N1—H1	0.8600	C10—H10A	0.9600
C1—H1A	0.9600	C10—H10B	0.9600
C1—H1B	0.9600	C10—H10C	0.9600
C1—H1C	0.9600	C11—H11A	0.9600
C3—C4	1.365 (2)	C11—H11B	0.9600
C3—C8	1.382 (2)	C11—H11C	0.9600
C2—O2—C3	116.85 (11)	C7—C6—H6	121.7
C4—O3—C9	105.66 (12)	C8—C7—C6	121.86 (16)
C5—O4—C9	106.26 (12)	C8—C7—H7	119.1
C2—N1—C1	121.84 (14)	C6—C7—H7	119.1
C2—N1—H1	119.1	C7—C8—C3	120.35 (16)
C1—N1—H1	119.1	C7—C8—H8	119.8
N1—C1—H1A	109.5	C3—C8—H8	119.8
N1—C1—H1B	109.5	O4—C9—O3	105.58 (12)
H1A—C1—H1B	109.5	O4—C9—C10	109.58 (15)
N1—C1—H1C	109.5	O3—C9—C10	107.98 (14)
H1A—C1—H1C	109.5	O4—C9—C11	108.10 (14)
H1B—C1—H1C	109.5	O3—C9—C11	109.30 (14)
O1—C2—N1	126.32 (15)	C10—C9—C11	115.83 (16)
O1—C2—O2	122.75 (14)	C9—C10—H10A	109.5
N1—C2—O2	110.93 (13)	C9—C10—H10B	109.5
C4—C3—C8	117.95 (16)	H10A—C10—H10B	109.5
C4—C3—O2	121.84 (13)	C9—C10—H10C	109.5
C8—C3—O2	120.08 (14)	H10A—C10—H10C	109.5
O3—C4—C3	128.60 (14)	H10B—C10—H10C	109.5
O3—C4—C5	110.59 (13)	C9—C11—H11A	109.5
C3—C4—C5	120.80 (14)	C9—C11—H11B	109.5
C6—C5—O4	128.11 (16)	H11A—C11—H11B	109.5
C6—C5—C4	122.36 (15)	C9—C11—H11C	109.5
O4—C5—C4	109.50 (13)	H11A—C11—H11C	109.5
C5—C6—C7	116.66 (17)	H11B—C11—H11C	109.5
C5—C6—H6	121.7
C1—N1—C2—O1	0.8 (2)	C3—C4—C5—C6	−0.5 (2)
C1—N1—C2—O2	−179.66 (13)	O3—C4—C5—O4	−1.11 (17)
C3—O2—C2—O1	−3.81 (19)	C3—C4—C5—O4	177.83 (13)
C3—O2—C2—N1	176.62 (12)	O4—C5—C6—C7	−177.16 (15)
C2—O2—C3—C4	−68.19 (17)	C4—C5—C6—C7	0.8 (2)
C2—O2—C3—C8	116.03 (15)	C5—C6—C7—C8	−0.4 (3)
C9—O3—C4—C3	172.56 (15)	C6—C7—C8—C3	−0.3 (3)
C9—O3—C4—C5	−8.60 (16)	C4—C3—C8—C7	0.6 (2)
C8—C3—C4—O3	178.46 (14)	O2—C3—C8—C7	176.56 (14)
O2—C3—C4—O3	2.6 (2)	C5—O4—C9—O3	−15.26 (16)
C8—C3—C4—C5	−0.3 (2)	C5—O4—C9—C10	−131.32 (15)
O2—C3—C4—C5	−176.13 (13)	C5—O4—C9—C11	101.61 (15)
C9—O4—C5—C6	−171.39 (16)	C4—O3—C9—O4	14.55 (15)
C9—O4—C5—C4	10.45 (17)	C4—O3—C9—C10	131.69 (14)
O3—C4—C5—C6	−179.39 (14)	C4—O3—C9—C11	−101.52 (15)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1i	0.86	2.01	2.819 (3)	157

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1i	0.86	2.01	2.819 (3)	157

Symmetry code: (i) .