Ethyl 5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxyl-ate.

The molecule of the title compound, C(10)H(13)NO(3), is approximately planar. A network of N-H⋯O and weak C-H⋯O hydrogen bonds helps to consolidate the crystal structure.

Related literature

For related literature, see: Sun et al. (2002 ▶). For details of the synthesis, see: Tang et al. (1999 ▶).

Experimental

Crystal data

C10H13NO3

M = 195.21

Monoclinic,

a = 3.9830 (8) Å

b = 15.572 (3) Å

c = 16.213 (3) Å

β = 96.96 (3)°

V = 998.2 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 293 (2) K

0.20 × 0.05 × 0.05 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.981, T max = 0.995

2069 measured reflections

1798 independent reflections

935 reflections with I > 2σ(I)

R int = 0.021

3 standard reflections every 200 reflections intensity decay: none

Refinement

R[F 2 > 2σ(F 2)] = 0.083

wR(F 2) = 0.190

S = 1.03

1798 reflections

127 parameters

H-atom parameters constrained

Δρmax = 0.16 e Å−3

Δρmin = −0.17 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: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808014542/hb2732sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808014542/hb2732Isup2.hkl

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

C10H13NO3	F000 = 416
Mr = 195.21	Dx = 1.299 Mg m−3
Monoclinic, P21/n	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 25 reflections
a = 3.9830 (8) Å	θ = 9–12º
b = 15.572 (3) Å	µ = 0.10 mm−1
c = 16.213 (3) Å	T = 293 (2) K
β = 96.96 (3)º	Needle, colourless
V = 998.2 (3) Å3	0.20 × 0.05 × 0.05 mm
Z = 4

Enraf–Nonius CAD-4 diffractometer	Rint = 0.021
Radiation source: fine-focus sealed tube	θmax = 25.2º
Monochromator: graphite	θmin = 1.8º
T = 293(2) K	h = −4→4
ω/2θ scans	k = 0→18
Absorption correction: ψ scan(North et al., 1968)	l = 0→19
Tmin = 0.981, Tmax = 0.995	3 standard reflections
2069 measured reflections	every 200 reflections
1798 independent reflections	intensity decay: none
935 reflections with I > 2σ(I)

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)] = 0.083	H-atom parameters constrained
wR(F2) = 0.190	w = 1/[σ2(Fo2) + (0.06P)2 + 0.5P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max < 0.001
1798 reflections	Δρmax = 0.16 e Å−3
127 parameters	Δρmin = −0.17 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: 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
N	0.3042 (9)	−0.0589 (2)	0.60096 (19)	0.0712 (11)
H0A	0.1844	−0.0604	0.5531	0.085*
O1	0.0871 (10)	0.11115 (17)	0.55062 (19)	0.0982 (12)
C1	0.7132 (14)	0.0521 (3)	0.7869 (3)	0.0900 (16)
H1A	0.8505	0.0210	0.8296	0.135*
H1B	0.5247	0.0773	0.8096	0.135*
H1C	0.8459	0.0965	0.7656	0.135*
O2	0.8180 (10)	−0.23224 (19)	0.76904 (18)	0.0989 (12)
C2	0.5870 (11)	−0.0078 (3)	0.7184 (2)	0.0619 (11)
O3	0.9364 (8)	−0.11553 (16)	0.84573 (16)	0.0802 (10)
C3	0.6177 (10)	−0.0982 (2)	0.7165 (2)	0.0575 (10)
C4	0.4352 (13)	−0.1260 (3)	0.6409 (3)	0.0781 (14)
C5	0.3840 (12)	0.0144 (2)	0.6459 (2)	0.0719 (13)
C6	0.3837 (13)	−0.2149 (3)	0.6079 (3)	0.0840 (15)
H6A	0.2464	−0.2132	0.5550	0.126*
H6B	0.2725	−0.2487	0.6460	0.126*
H6C	0.5989	−0.2401	0.6015	0.126*
C7	0.2893 (14)	0.0965 (3)	0.6142 (3)	0.0825 (15)
H7A	0.3857	0.1437	0.6432	0.099*
C8	0.7874 (12)	−0.1552 (3)	0.7771 (2)	0.0656 (11)
C9	1.1202 (13)	−0.1682 (3)	0.9080 (2)	0.0797 (14)
H9A	1.3017	−0.1981	0.8852	0.096*
H9B	0.9713	−0.2105	0.9283	0.096*
C10	1.2602 (13)	−0.1105 (3)	0.9765 (3)	0.0888 (15)
H10A	1.3865	−0.1437	1.0195	0.133*
H10B	1.0782	−0.0815	0.9988	0.133*
H10C	1.4063	−0.0688	0.9556	0.133*

	U11	U22	U33	U12	U13	U23
N	0.073 (3)	0.071 (2)	0.0652 (18)	0.004 (2)	−0.0076 (18)	0.0032 (16)
O1	0.125 (3)	0.0727 (18)	0.0864 (19)	0.006 (2)	−0.029 (2)	0.0039 (15)
C1	0.110 (5)	0.072 (3)	0.086 (3)	−0.002 (3)	0.001 (3)	−0.004 (2)
O2	0.130 (4)	0.0705 (19)	0.092 (2)	0.009 (2)	−0.004 (2)	−0.0027 (15)
C2	0.053 (3)	0.076 (3)	0.0595 (19)	0.001 (2)	0.0175 (18)	0.0012 (18)
O3	0.094 (3)	0.0629 (16)	0.0791 (18)	0.0052 (19)	−0.0082 (17)	0.0004 (14)
C3	0.047 (3)	0.069 (2)	0.060 (2)	−0.007 (2)	0.0210 (18)	0.0007 (17)
C4	0.088 (4)	0.069 (3)	0.077 (3)	−0.020 (3)	0.007 (2)	0.002 (2)
C5	0.071 (3)	0.055 (2)	0.083 (3)	0.010 (2)	−0.017 (2)	−0.002 (2)
C6	0.094 (4)	0.071 (3)	0.086 (3)	−0.011 (3)	0.003 (3)	−0.017 (2)
C7	0.101 (4)	0.075 (3)	0.069 (2)	−0.009 (3)	0.001 (3)	0.003 (2)
C8	0.061 (3)	0.065 (2)	0.074 (2)	0.002 (3)	0.020 (2)	−0.002 (2)
C9	0.090 (4)	0.068 (2)	0.077 (3)	0.012 (3)	−0.003 (3)	0.003 (2)
C10	0.084 (4)	0.089 (3)	0.091 (3)	0.012 (3)	−0.003 (3)	0.007 (2)

N—C4	1.304 (5)	C3—C8	1.432 (5)
N—C5	1.370 (5)	C4—C6	1.489 (5)
N—H0A	0.8600	C5—C7	1.412 (5)
O1—C7	1.250 (5)	C6—H6A	0.9600
C1—C2	1.490 (5)	C6—H6B	0.9600
C1—H1A	0.9600	C6—H6C	0.9600
C1—H1B	0.9600	C7—H7A	0.9300
C1—H1C	0.9600	C9—C10	1.484 (5)
O2—C8	1.214 (4)	C9—H9A	0.9700
C2—C5	1.388 (5)	C9—H9B	0.9700
C2—C3	1.414 (5)	C10—H10A	0.9600
O3—C8	1.346 (4)	C10—H10B	0.9600
O3—C9	1.431 (4)	C10—H10C	0.9600
C3—C4	1.415 (5)
C4—N—C5	110.5 (3)	C4—C6—H6B	109.5
C4—N—H0A	124.7	H6A—C6—H6B	109.5
C5—N—H0A	124.7	C4—C6—H6C	109.5
C2—C1—H1A	109.5	H6A—C6—H6C	109.5
C2—C1—H1B	109.5	H6B—C6—H6C	109.5
H1A—C1—H1B	109.5	O1—C7—C5	125.6 (4)
C2—C1—H1C	109.5	O1—C7—H7A	117.2
H1A—C1—H1C	109.5	C5—C7—H7A	117.2
H1B—C1—H1C	109.5	O2—C8—O3	120.2 (4)
C5—C2—C3	105.8 (3)	O2—C8—C3	125.7 (4)
C5—C2—C1	125.8 (4)	O3—C8—C3	114.0 (3)
C3—C2—C1	128.1 (4)	O3—C9—C10	107.2 (3)
C8—O3—C9	117.2 (3)	O3—C9—H9A	110.3
C2—C3—C4	106.7 (3)	C10—C9—H9A	110.3
C2—C3—C8	129.5 (4)	O3—C9—H9B	110.3
C4—C3—C8	123.7 (4)	C10—C9—H9B	110.3
N—C4—C3	108.5 (3)	H9A—C9—H9B	108.5
N—C4—C6	122.5 (4)	C9—C10—H10A	109.5
C3—C4—C6	129.0 (4)	C9—C10—H10B	109.5
N—C5—C2	108.5 (3)	H10A—C10—H10B	109.5
N—C5—C7	121.8 (3)	C9—C10—H10C	109.5
C2—C5—C7	129.5 (4)	H10A—C10—H10C	109.5
C4—C6—H6A	109.5	H10B—C10—H10C	109.5
C5—C2—C3—C4	1.3 (5)	C1—C2—C5—N	−176.2 (4)
C1—C2—C3—C4	175.6 (5)	C3—C2—C5—C7	−175.8 (5)
C5—C2—C3—C8	−177.2 (4)	C1—C2—C5—C7	9.7 (8)
C1—C2—C3—C8	−2.9 (8)	N—C5—C7—O1	11.4 (8)
C5—N—C4—C3	−0.7 (5)	C2—C5—C7—O1	−175.2 (5)
C5—N—C4—C6	178.6 (5)	C9—O3—C8—O2	−1.6 (7)
C2—C3—C4—N	−0.4 (5)	C9—O3—C8—C3	−178.1 (4)
C8—C3—C4—N	178.2 (4)	C2—C3—C8—O2	−175.8 (5)
C2—C3—C4—C6	−179.6 (5)	C4—C3—C8—O2	5.8 (8)
C8—C3—C4—C6	−0.9 (8)	C2—C3—C8—O3	0.4 (7)
C4—N—C5—C2	1.6 (5)	C4—C3—C8—O3	−177.9 (4)
C4—N—C5—C7	176.2 (5)	C8—O3—C9—C10	179.8 (4)
C3—C2—C5—N	−1.7 (5)

D—H···A	D—H	H···A	D···A	D—H···A
N—H0A···O1i	0.86	2.04	2.864 (5)	159
C1—H1A···O3	0.96	2.16	2.882 (5)	131
C6—H6A···O1i	0.96	2.58	3.401 (6)	143
C7—H7A···O2ii	0.93	2.60	3.525 (6)	176

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N—H0A⋯O1i	0.86	2.04	2.864 (5)	159
C1—H1A⋯O3	0.96	2.16	2.882 (5)	131
C6—H6A⋯O1i	0.96	2.58	3.401 (6)	143
C7—H7A⋯O2ii	0.93	2.60	3.525 (6)	176

Symmetry codes: (i) ; (ii) .