Ethyl 3,5-dimethyl-1H-pyrrole-2-carboxyl-ate.

In the title compound, C(9)H(13)NO(2), there are two independent mol-ecules per asymmetric unit. The mol-ecules are very similar and almost planar, with the ethoxy-carbonyl group anti to the pyrrole N atom. The two independent mol-ecules are joined into dimeric units by strong hydrogen bonds between NH groups and carbonyl O atoms.

Related literature

For general background, see: Bonnett (1995 ▶, 2000 ▶). For related structures, see: Paixão et al. (2002 ▶), Ramos Silva et al. (2002 ▶); Sobral & Rocha Gonsalves (2001 ▶).

Experimental

Crystal data

C9H13NO2

M = 167.20

Triclinic,

a = 8.1357 (2) Å

b = 10.5568 (2) Å

c = 12.1428 (2) Å

α = 101.5451 (13)°

β = 97.8791 (14)°

γ = 110.4821 (14)°

V = 932.52 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 293 (2) K

0.25 × 0.20 × 0.15 mm

Data collection

Bruker APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2000 ▶) T min = 0.899, T max = 0.987

20370 measured reflections

4456 independent reflections

2368 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.052

wR(F 2) = 0.182

S = 1.03

4456 reflections

223 parameters

H-atom parameters constrained

Δρmax = 0.20 e Å−3

Δρmin = −0.21 e Å−3

Data collection: SMART (Bruker, 2003 ▶); cell refinement: SAINT (Bruker, 2003 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEPII (Johnson, 1976 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808029929/bt2791sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808029929/bt2791Isup2.hkl

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

C9H13NO2	Z = 4
Mr = 167.20	F(000) = 360
Triclinic, P1	Dx = 1.191 Mg m−3
a = 8.1357 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.5568 (2) Å	Cell parameters from 3873 reflections
c = 12.1428 (2) Å	θ = 2.4–23.9°
α = 101.5451 (13)°	µ = 0.08 mm−1
β = 97.8791 (14)°	T = 293 K
γ = 110.4821 (14)°	Prism, colourless
V = 932.52 (4) Å3	0.25 × 0.20 × 0.15 mm

Bruker APEX CCD area-detector diffractometer	4456 independent reflections
Radiation source: fine-focus sealed tube	2368 reflections with I > 2σ(I)
graphite	Rint = 0.028
φ and ω scans	θmax = 28.0°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 2000)	h = −10→10
Tmin = 0.899, Tmax = 0.987	k = −13→13
20370 measured reflections	l = −15→15

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) = 0.182	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0939P)2 + 0.0508P] where P = (Fo2 + 2Fc2)/3
4456 reflections	(Δ/σ)max < 0.001
223 parameters	Δρmax = 0.20 e Å−3
0 restraints	Δρmin = −0.21 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
N1	0.2122 (2)	0.18401 (15)	0.96119 (12)	0.0526 (4)
H1	0.1472	0.1689	0.8941	0.063*
C1	0.2894 (2)	0.31179 (18)	1.04326 (14)	0.0483 (4)
C2	0.3837 (3)	0.29357 (19)	1.13867 (15)	0.0535 (5)
C3	0.3587 (3)	0.1515 (2)	1.11083 (17)	0.0620 (5)
H3	0.4060	0.1083	1.1589	0.074*
C4	0.2537 (3)	0.08658 (19)	1.00165 (17)	0.0561 (5)
C5	0.1877 (3)	−0.0621 (2)	0.92988 (19)	0.0745 (6)
H5A	0.0653	−0.0912	0.8891	0.112*
H5B	0.1938	−0.1218	0.9790	0.112*
H5C	0.2617	−0.0684	0.8756	0.112*
C6	0.4927 (3)	0.4029 (2)	1.24868 (16)	0.0700 (6)
H6A	0.5941	0.4716	1.2331	0.105*
H6B	0.5346	0.3594	1.3024	0.105*
H6C	0.4193	0.4476	1.2810	0.105*
C7	0.2626 (2)	0.43124 (19)	1.01696 (15)	0.0497 (4)
C8	0.3246 (3)	0.67311 (19)	1.08651 (16)	0.0598 (5)
H8A	0.1987	0.6598	1.0744	0.072*
H8B	0.3685	0.6956	1.0196	0.072*
C9	0.4325 (3)	0.7891 (2)	1.19379 (19)	0.0736 (6)
H9A	0.3901	0.7642	1.2595	0.110*
H9B	0.4191	0.8742	1.1869	0.110*
H9C	0.5573	0.8030	1.2035	0.110*
O1	0.34589 (17)	0.54785 (12)	1.10374 (10)	0.0571 (4)
O2	0.1739 (2)	0.42886 (14)	0.92727 (11)	0.0697 (4)
N2	−0.03335 (19)	0.33131 (15)	0.69754 (12)	0.0514 (4)
H2	0.0341	0.3455	0.7635	0.062*
C10	−0.0692 (3)	0.43124 (19)	0.65748 (16)	0.0532 (5)
C11	−0.1793 (3)	0.3672 (2)	0.54923 (17)	0.0581 (5)
H11	−0.2237	0.4120	0.5012	0.070*
C12	−0.2140 (2)	0.22325 (19)	0.52282 (15)	0.0511 (5)
C13	−0.1210 (2)	0.20295 (18)	0.61697 (14)	0.0470 (4)
C14	−0.3308 (3)	0.1161 (2)	0.41335 (16)	0.0666 (6)
H14A	−0.2676	0.0606	0.3829	0.100*
H14B	−0.3600	0.1628	0.3580	0.100*
H14C	−0.4397	0.0564	0.4290	0.100*
C15	0.0049 (3)	0.58075 (19)	0.72855 (18)	0.0681 (6)
H15A	−0.0667	0.5910	0.7837	0.102*
H15B	0.0018	0.6407	0.6791	0.102*
H15C	0.1270	0.6063	0.7684	0.102*
C16	−0.1000 (3)	0.08222 (19)	0.64427 (15)	0.0525 (5)
C17	−0.1825 (3)	−0.16323 (19)	0.58381 (18)	0.0635 (5)
H17A	−0.2223	−0.1772	0.6538	0.076*
H17B	−0.0591	−0.1565	0.5933	0.076*
C18	−0.3012 (3)	−0.2831 (2)	0.4826 (2)	0.0777 (7)
H18A	−0.4226	−0.2880	0.4734	0.116*
H18B	−0.2979	−0.3691	0.4953	0.116*
H18C	−0.2593	−0.2690	0.4141	0.116*
O3	−0.19388 (17)	−0.03673 (13)	0.56183 (10)	0.0574 (4)
O4	−0.0063 (2)	0.08520 (14)	0.73228 (12)	0.0806 (5)

	U11	U22	U33	U12	U13	U23
N1	0.0640 (10)	0.0477 (9)	0.0397 (8)	0.0212 (8)	0.0025 (7)	0.0053 (7)
C1	0.0532 (10)	0.0434 (10)	0.0407 (9)	0.0155 (8)	0.0037 (8)	0.0055 (8)
C2	0.0575 (11)	0.0533 (11)	0.0445 (10)	0.0198 (9)	0.0041 (8)	0.0099 (8)
C3	0.0759 (14)	0.0568 (12)	0.0565 (12)	0.0307 (11)	0.0067 (10)	0.0189 (10)
C4	0.0674 (12)	0.0478 (11)	0.0552 (11)	0.0256 (9)	0.0123 (9)	0.0133 (9)
C5	0.0935 (16)	0.0467 (12)	0.0772 (15)	0.0282 (11)	0.0119 (12)	0.0069 (10)
C6	0.0797 (15)	0.0690 (14)	0.0472 (11)	0.0236 (11)	−0.0088 (10)	0.0103 (10)
C7	0.0534 (11)	0.0470 (11)	0.0408 (10)	0.0160 (8)	0.0037 (8)	0.0059 (8)
C8	0.0741 (13)	0.0482 (11)	0.0566 (12)	0.0256 (10)	0.0108 (10)	0.0124 (9)
C9	0.0911 (16)	0.0509 (12)	0.0669 (14)	0.0229 (11)	0.0142 (12)	0.0014 (10)
O1	0.0726 (9)	0.0436 (7)	0.0455 (7)	0.0207 (6)	−0.0015 (6)	0.0050 (6)
O2	0.0918 (11)	0.0559 (8)	0.0498 (8)	0.0314 (8)	−0.0130 (7)	0.0039 (6)
N2	0.0561 (9)	0.0459 (9)	0.0428 (8)	0.0157 (7)	0.0011 (7)	0.0061 (7)
C10	0.0583 (11)	0.0456 (11)	0.0535 (11)	0.0191 (9)	0.0097 (9)	0.0126 (9)
C11	0.0639 (12)	0.0531 (12)	0.0538 (11)	0.0222 (9)	0.0002 (9)	0.0166 (9)
C12	0.0511 (10)	0.0515 (11)	0.0439 (10)	0.0166 (9)	0.0035 (8)	0.0089 (8)
C13	0.0496 (10)	0.0423 (10)	0.0403 (9)	0.0133 (8)	0.0035 (8)	0.0050 (7)
C14	0.0691 (13)	0.0649 (13)	0.0491 (11)	0.0186 (11)	−0.0086 (10)	0.0081 (10)
C15	0.0796 (15)	0.0451 (12)	0.0702 (13)	0.0218 (10)	0.0066 (11)	0.0068 (10)
C16	0.0580 (11)	0.0476 (11)	0.0426 (10)	0.0169 (9)	0.0017 (9)	0.0050 (8)
C17	0.0701 (13)	0.0484 (12)	0.0643 (13)	0.0226 (10)	0.0037 (10)	0.0073 (10)
C18	0.0850 (16)	0.0475 (12)	0.0825 (16)	0.0204 (11)	0.0047 (12)	−0.0019 (11)
O3	0.0664 (8)	0.0428 (7)	0.0508 (8)	0.0179 (6)	−0.0027 (6)	0.0029 (6)
O4	0.1088 (12)	0.0548 (9)	0.0572 (9)	0.0290 (8)	−0.0237 (8)	0.0037 (7)

N1—C4	1.346 (2)	N2—C10	1.348 (2)
N1—C1	1.380 (2)	N2—C13	1.380 (2)
N1—H1	0.8600	N2—H2	0.8600
C1—C2	1.384 (2)	C10—C11	1.373 (3)
C1—C7	1.440 (2)	C10—C15	1.498 (2)
C2—C3	1.404 (3)	C11—C12	1.405 (2)
C2—C6	1.498 (3)	C11—H11	0.9300
C3—C4	1.369 (3)	C12—C13	1.378 (2)
C3—H3	0.9300	C12—C14	1.500 (2)
C4—C5	1.498 (3)	C13—C16	1.438 (3)
C5—H5A	0.9600	C14—H14A	0.9600
C5—H5B	0.9600	C14—H14B	0.9600
C5—H5C	0.9600	C14—H14C	0.9600
C6—H6A	0.9600	C15—H15A	0.9600
C6—H6B	0.9600	C15—H15B	0.9600
C6—H6C	0.9600	C15—H15C	0.9600
C7—O2	1.212 (2)	C16—O4	1.213 (2)
C7—O1	1.336 (2)	C16—O3	1.333 (2)
C8—O1	1.443 (2)	C17—O3	1.444 (2)
C8—C9	1.504 (3)	C17—C18	1.497 (3)
C8—H8A	0.9700	C17—H17A	0.9700
C8—H8B	0.9700	C17—H17B	0.9700
C9—H9A	0.9600	C18—H18A	0.9600
C9—H9B	0.9600	C18—H18B	0.9600
C9—H9C	0.9600	C18—H18C	0.9600
C4—N1—C1	109.98 (15)	C10—N2—C13	109.89 (15)
C4—N1—H1	125.0	C10—N2—H2	125.1
C1—N1—H1	125.0	C13—N2—H2	125.1
N1—C1—C2	107.62 (15)	N2—C10—C11	107.26 (16)
N1—C1—C7	119.00 (15)	N2—C10—C15	121.47 (17)
C2—C1—C7	133.38 (16)	C11—C10—C15	131.26 (18)
C1—C2—C3	105.90 (16)	C10—C11—C12	108.90 (17)
C1—C2—C6	127.36 (17)	C10—C11—H11	125.6
C3—C2—C6	126.73 (17)	C12—C11—H11	125.6
C4—C3—C2	109.18 (17)	C13—C12—C11	106.15 (16)
C4—C3—H3	125.4	C13—C12—C14	128.26 (17)
C2—C3—H3	125.4	C11—C12—C14	125.59 (17)
N1—C4—C3	107.32 (16)	C12—C13—N2	107.79 (15)
N1—C4—C5	121.31 (18)	C12—C13—C16	133.95 (16)
C3—C4—C5	131.37 (19)	N2—C13—C16	118.26 (15)
C4—C5—H5A	109.5	C12—C14—H14A	109.5
C4—C5—H5B	109.5	C12—C14—H14B	109.5
H5A—C5—H5B	109.5	H14A—C14—H14B	109.5
C4—C5—H5C	109.5	C12—C14—H14C	109.5
H5A—C5—H5C	109.5	H14A—C14—H14C	109.5
H5B—C5—H5C	109.5	H14B—C14—H14C	109.5
C2—C6—H6A	109.5	C10—C15—H15A	109.5
C2—C6—H6B	109.5	C10—C15—H15B	109.5
H6A—C6—H6B	109.5	H15A—C15—H15B	109.5
C2—C6—H6C	109.5	C10—C15—H15C	109.5
H6A—C6—H6C	109.5	H15A—C15—H15C	109.5
H6B—C6—H6C	109.5	H15B—C15—H15C	109.5
O2—C7—O1	122.56 (16)	O4—C16—O3	121.97 (17)
O2—C7—C1	124.92 (16)	O4—C16—C13	124.71 (16)
O1—C7—C1	112.52 (15)	O3—C16—C13	113.32 (15)
O1—C8—C9	106.73 (15)	O3—C17—C18	107.56 (16)
O1—C8—H8A	110.4	O3—C17—H17A	110.2
C9—C8—H8A	110.4	C18—C17—H17A	110.2
O1—C8—H8B	110.4	O3—C17—H17B	110.2
C9—C8—H8B	110.4	C18—C17—H17B	110.2
H8A—C8—H8B	108.6	H17A—C17—H17B	108.5
C8—C9—H9A	109.5	C17—C18—H18A	109.5
C8—C9—H9B	109.5	C17—C18—H18B	109.5
H9A—C9—H9B	109.5	H18A—C18—H18B	109.5
C8—C9—H9C	109.5	C17—C18—H18C	109.5
H9A—C9—H9C	109.5	H18A—C18—H18C	109.5
H9B—C9—H9C	109.5	H18B—C18—H18C	109.5
C7—O1—C8	116.76 (13)	C16—O3—C17	116.64 (14)
C4—N1—C1—C2	0.3 (2)	C13—N2—C10—C11	−0.8 (2)
C4—N1—C1—C7	179.58 (15)	C13—N2—C10—C15	178.44 (16)
N1—C1—C2—C3	−0.4 (2)	N2—C10—C11—C12	0.8 (2)
C7—C1—C2—C3	−179.57 (19)	C15—C10—C11—C12	−178.28 (19)
N1—C1—C2—C6	178.72 (18)	C10—C11—C12—C13	−0.6 (2)
C7—C1—C2—C6	−0.4 (3)	C10—C11—C12—C14	179.03 (18)
C1—C2—C3—C4	0.4 (2)	C11—C12—C13—N2	0.1 (2)
C6—C2—C3—C4	−178.74 (19)	C14—C12—C13—N2	−179.49 (17)
C1—N1—C4—C3	0.0 (2)	C11—C12—C13—C16	−179.8 (2)
C1—N1—C4—C5	−179.76 (16)	C14—C12—C13—C16	0.6 (3)
C2—C3—C4—N1	−0.3 (2)	C10—N2—C13—C12	0.4 (2)
C2—C3—C4—C5	179.4 (2)	C10—N2—C13—C16	−179.68 (15)
N1—C1—C7—O2	1.0 (3)	C12—C13—C16—O4	177.7 (2)
C2—C1—C7—O2	−179.9 (2)	N2—C13—C16—O4	−2.2 (3)
N1—C1—C7—O1	−179.56 (14)	C12—C13—C16—O3	−1.7 (3)
C2—C1—C7—O1	−0.5 (3)	N2—C13—C16—O3	178.41 (15)
O2—C7—O1—C8	0.4 (3)	O4—C16—O3—C17	1.7 (3)
C1—C7—O1—C8	−178.98 (15)	C13—C16—O3—C17	−178.86 (15)
C9—C8—O1—C7	−178.86 (15)	C18—C17—O3—C16	178.37 (16)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O4	0.86	2.02	2.857 (2)	166.
N2—H2···O2	0.86	2.00	2.834 (2)	163.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O4	0.86	2.02	2.857 (2)	166
N2—H2⋯O2	0.86	2.00	2.834 (2)	163