Methyl (1H-pyrrol-2-ylcarbonyl-amino)acetate.

In the crystal structure of the title compound, C(8)H(10)N(2)O(3), mol-ecules are linked by N-H⋯O hydrogen bonds, forming ribbons of centrosymmetric dimers extending along the c axis.

Related literature

For related literature, see: Banwell et al. (2006 ▶); Bernstein et al. (1995 ▶); Faulkner (2002 ▶); Sosa et al. (2002 ▶); Zeng (2006 ▶); Zeng et al. (2007 ▶).

Experimental

Crystal data

C8H10N2O3

M = 182.18

Monoclinic,

a = 11.3398 (19) Å

b = 5.0732 (9) Å

c = 16.500 (3) Å

β = 108.060 (3)°

V = 902.5 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 173 (2) K

0.48 × 0.41 × 0.21 mm

Data collection

Bruker SMART 1K CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1997 ▶) T min = 0.952, T max = 0.979

4219 measured reflections

1576 independent reflections

1417 reflections with I > 2σ(I)

R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.052

wR(F 2) = 0.166

S = 1.10

1576 reflections

119 parameters

H-atom parameters constrained

Δρmax = 0.21 e Å−3

Δρmin = −0.31 e Å−3

Data collection: SMART (Bruker, 1999 ▶); cell refinement: SAINT-Plus (Bruker, 1999 ▶); data reduction: SAINT-Plus; 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/S1600536808027451/cf2214sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808027451/cf2214Isup2.hkl

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

Enhanced figure: interactive version of Fig. 1

C8H10N2O3	Dx = 1.341 Mg m−3
Mr = 182.18	Melting point: 420 K
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 11.3398 (19) Å	Cell parameters from 3468 reflections
b = 5.0732 (9) Å	θ = 2.6–27.0°
c = 16.500 (3) Å	µ = 0.10 mm−1
β = 108.060 (3)°	T = 173 K
V = 902.5 (3) Å3	Block, light yellow
Z = 4	0.48 × 0.41 × 0.21 mm
F(000) = 384

Bruker SMART 1K CCD area-detector diffractometer	1576 independent reflections
Radiation source: fine-focus sealed tube	1417 reflections with I > 2σ(I)
graphite	Rint = 0.033
φ and ω scans	θmax = 25.0°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1997)	h = −13→13
Tmin = 0.952, Tmax = 0.979	k = −6→5
4219 measured reflections	l = −16→19

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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.166	H-atom parameters constrained
S = 1.10	w = 1/[σ2(Fo2) + (0.1092P)2 + 0.2414P] where P = (Fo2 + 2Fc2)/3
1576 reflections	(Δ/σ)max = 0.001
119 parameters	Δρmax = 0.21 e Å−3
0 restraints	Δρmin = −0.31 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	0.89632 (13)	0.2572 (2)	0.45357 (8)	0.0387 (4)
O2	0.63332 (13)	0.2895 (3)	0.31013 (8)	0.0391 (4)
N2	0.85781 (14)	0.5697 (3)	0.35256 (9)	0.0343 (4)
H2	0.8777	0.6472	0.3109	0.041*
O3	0.58657 (13)	0.4945 (3)	0.41547 (9)	0.0513 (5)
C3	1.06971 (17)	0.3350 (4)	0.29921 (12)	0.0364 (5)
H3	1.0414	0.4778	0.2608	0.044*
N1	1.08932 (14)	0.0465 (3)	0.40331 (10)	0.0343 (4)
H1	1.0773	−0.0386	0.4466	0.041*
C5	0.92253 (15)	0.3607 (3)	0.39334 (10)	0.0306 (5)
C6	0.75496 (17)	0.6645 (3)	0.37859 (12)	0.0352 (5)
H6A	0.7211	0.8266	0.3464	0.042*
H6B	0.7847	0.7099	0.4400	0.042*
C7	0.65395 (17)	0.4608 (3)	0.36324 (11)	0.0329 (5)
C4	1.02305 (17)	0.2601 (3)	0.36367 (11)	0.0313 (5)
C1	1.17634 (18)	−0.0142 (4)	0.36582 (13)	0.0394 (5)
H1A	1.2344	−0.1546	0.3817	0.047*
C2	1.16634 (18)	0.1618 (4)	0.30085 (13)	0.0413 (5)
H2A	1.2159	0.1652	0.2638	0.050*
C8	0.4845 (3)	0.3088 (6)	0.40341 (18)	0.0720 (9)
H8A	0.4282	0.3231	0.3450	0.108*
H8B	0.4391	0.3494	0.4437	0.108*
H8C	0.5174	0.1290	0.4135	0.108*

	U11	U22	U33	U12	U13	U23
O1	0.0451 (8)	0.0384 (8)	0.0386 (8)	0.0040 (6)	0.0217 (6)	0.0103 (5)
O2	0.0448 (8)	0.0368 (7)	0.0392 (8)	−0.0018 (6)	0.0180 (6)	−0.0094 (6)
N2	0.0403 (9)	0.0297 (8)	0.0388 (9)	0.0010 (6)	0.0207 (7)	0.0065 (6)
O3	0.0508 (9)	0.0644 (10)	0.0499 (9)	−0.0184 (7)	0.0319 (8)	−0.0247 (7)
C3	0.0388 (10)	0.0350 (10)	0.0387 (10)	−0.0025 (8)	0.0166 (8)	0.0063 (8)
N1	0.0376 (9)	0.0304 (8)	0.0385 (9)	−0.0018 (6)	0.0170 (7)	0.0044 (6)
C5	0.0330 (9)	0.0288 (10)	0.0315 (9)	−0.0055 (7)	0.0120 (8)	0.0008 (7)
C6	0.0423 (11)	0.0274 (9)	0.0394 (10)	0.0022 (7)	0.0178 (8)	−0.0003 (7)
C7	0.0383 (10)	0.0322 (9)	0.0304 (9)	0.0046 (7)	0.0141 (8)	−0.0008 (7)
C4	0.0341 (9)	0.0270 (9)	0.0337 (10)	−0.0042 (7)	0.0119 (8)	0.0006 (7)
C1	0.0368 (10)	0.0345 (10)	0.0502 (12)	0.0011 (8)	0.0184 (9)	0.0004 (8)
C2	0.0416 (11)	0.0416 (11)	0.0492 (12)	−0.0029 (8)	0.0265 (9)	0.0022 (9)
C8	0.0677 (16)	0.097 (2)	0.0690 (16)	−0.0400 (15)	0.0468 (14)	−0.0364 (15)

O1—C5	1.239 (2)	N1—H1	0.880
O2—C7	1.204 (2)	C5—C4	1.465 (2)
N2—C5	1.345 (2)	C6—C7	1.505 (3)
N2—C6	1.444 (2)	C6—H6A	0.990
N2—H2	0.880	C6—H6B	0.990
O3—C7	1.328 (2)	C1—C2	1.373 (3)
O3—C8	1.458 (3)	C1—H1A	0.950
C3—C4	1.380 (2)	C2—H2A	0.950
C3—C2	1.398 (3)	C8—H8A	0.980
C3—H3	0.950	C8—H8B	0.980
N1—C1	1.353 (2)	C8—H8C	0.980
N1—C4	1.365 (2)
C5—N2—C6	118.64 (14)	O2—C7—O3	122.96 (17)
C5—N2—H2	120.7	O2—C7—C6	125.73 (17)
C6—N2—H2	120.7	O3—C7—C6	111.30 (15)
C7—O3—C8	114.87 (16)	N1—C4—C3	107.59 (16)
C4—C3—C2	107.31 (17)	N1—C4—C5	119.11 (15)
C4—C3—H3	126.3	C3—C4—C5	133.30 (17)
C2—C3—H3	126.3	N1—C1—C2	108.28 (17)
C1—N1—C4	109.46 (15)	N1—C1—H1A	125.9
C1—N1—H1	125.3	C2—C1—H1A	125.9
C4—N1—H1	125.3	C1—C2—C3	107.37 (17)
O1—C5—N2	120.38 (16)	C1—C2—H2A	126.3
O1—C5—C4	121.72 (16)	C3—C2—H2A	126.3
N2—C5—C4	117.89 (14)	O3—C8—H8A	109.5
N2—C6—C7	111.34 (14)	O3—C8—H8B	109.5
N2—C6—H6A	109.4	H8A—C8—H8B	109.5
C7—C6—H6A	109.4	O3—C8—H8C	109.5
N2—C6—H6B	109.4	H8A—C8—H8C	109.5
C7—C6—H6B	109.4	H8B—C8—H8C	109.5
H6A—C6—H6B	108.0
C6—N2—C5—O1	−2.1 (2)	C2—C3—C4—N1	−0.2 (2)
C6—N2—C5—C4	177.39 (15)	C2—C3—C4—C5	−179.42 (19)
C5—N2—C6—C7	−63.6 (2)	O1—C5—C4—N1	0.2 (3)
C8—O3—C7—O2	−0.4 (3)	N2—C5—C4—N1	−179.30 (14)
C8—O3—C7—C6	178.56 (19)	O1—C5—C4—C3	179.36 (19)
N2—C6—C7—O2	−26.5 (3)	N2—C5—C4—C3	−0.1 (3)
N2—C6—C7—O3	154.55 (16)	C4—N1—C1—C2	−0.1 (2)
C1—N1—C4—C3	0.2 (2)	N1—C1—C2—C3	0.0 (2)
C1—N1—C4—C5	179.57 (16)	C4—C3—C2—C1	0.1 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1i	0.88	1.93	2.782 (2)	162.
N2—H2···O2ii	0.88	2.09	2.9372 (19)	161.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1i	0.88	1.93	2.782 (2)	162
N2—H2⋯O2ii	0.88	2.09	2.9372 (19)	161

Symmetry codes: (i) ; (ii) .