rac-Dimethyl 2-(1H-pyrrole-2-carboxamido)-butane-dioate.

The title compound, C(11)H(14)N(2)O(5), was synthesized by condensation of (RS)-2-amino-succinic acid dimethyl ester with 2-trichloro-acetyl-pyrrole at room temperature. The amide group is twisted by 7.4 (1)° from the plane of the pyrrole ring. In the crystal, mol-ecules are linked by inter-molecular N-H⋯O hydrogen bonds into chains extending along the c axis.

Related literature

For the bioactivity of pyrrole derivatives, see: Fabio et al. (2007 ▶); Banwell et al. (2006 ▶). For related structures, see: Zeng et al. (2010 ▶); Li et al. (2009 ▶); Liu et al. (2006 ▶).

Experimental

Crystal data

C11H14N2O5

M = 254.24

Monoclinic,

a = 9.1387 (8) Å

b = 15.2715 (11) Å

c = 9.6238 (9) Å

β = 105.750 (9)°

V = 1292.69 (19) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 293 K

0.48 × 0.26 × 0.21 mm

Data collection

Oxford Gemini S Ultra area-detector diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010 ▶) T min = 0.952, T max = 0.978

5286 measured reflections

2534 independent reflections

1563 reflections with I > 2σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.059

wR(F 2) = 0.163

S = 1.05

2534 reflections

165 parameters

H-atom parameters constrained

Δρmax = 0.18 e Å−3

Δρmin = −0.21 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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/S1600536811007148/cv5056sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811007148/cv5056Isup2.hkl

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

C11H14N2O5	Dx = 1.306 Mg m−3
Mr = 254.24	Melting point: 384 K
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 9.1387 (8) Å	Cell parameters from 1891 reflections
b = 15.2715 (11) Å	θ = 3.5–29.4°
c = 9.6238 (9) Å	µ = 0.10 mm−1
β = 105.750 (9)°	T = 293 K
V = 1292.69 (19) Å3	Prism, light yellow
Z = 4	0.48 × 0.26 × 0.21 mm
F(000) = 536

Oxford Gemini S Ultra area-detector diffractometer	2534 independent reflections
Radiation source: fine-focus sealed tube	1563 reflections with I > 2σ(I)
graphite	Rint = 0.032
φ and ω scans	θmax = 26.0°, θmin = 3.5°
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	h = −11→7
Tmin = 0.952, Tmax = 0.978	k = −15→18
5286 measured reflections	l = −11→11

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)] = 0.059	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.163	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0623P)2 + 0.3001P] where P = (Fo2 + 2Fc2)/3
2534 reflections	(Δ/σ)max = 0.012
165 parameters	Δρmax = 0.18 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
O1	0.8723 (2)	0.22381 (12)	0.93777 (18)	0.0598 (6)
N2	0.8981 (2)	0.20231 (12)	0.7148 (2)	0.0454 (5)
H2A	0.8870	0.2226	0.6292	0.055*
N1	0.7370 (2)	0.36401 (14)	0.6269 (2)	0.0552 (6)
H1A	0.7730	0.3439	0.5594	0.066*
C5	0.8472 (3)	0.24881 (15)	0.8093 (2)	0.0422 (6)
C4	0.7615 (3)	0.32843 (16)	0.7622 (3)	0.0429 (6)
O3	0.9219 (2)	−0.02724 (12)	0.8003 (3)	0.0796 (7)
O5	1.2703 (2)	0.15643 (15)	0.5747 (3)	0.0843 (7)
C7	0.8551 (3)	0.04766 (17)	0.7534 (3)	0.0522 (7)
C3	0.6833 (3)	0.37952 (17)	0.8361 (3)	0.0546 (7)
H3	0.6793	0.3712	0.9307	0.065*
C6	0.9717 (3)	0.11846 (15)	0.7531 (3)	0.0482 (7)
H6	1.0386	0.1232	0.8515	0.058*
C9	1.2137 (3)	0.15003 (18)	0.6855 (4)	0.0585 (7)
C8	1.0705 (3)	0.09670 (17)	0.6529 (3)	0.0546 (7)
H8A	1.0969	0.0350	0.6622	0.065*
H8B	1.0127	0.1072	0.5538	0.065*
O2	0.7223 (2)	0.05805 (14)	0.7203 (3)	0.0953 (9)
O4	1.2728 (3)	0.18044 (18)	0.8018 (3)	0.1036 (9)
C2	0.6111 (3)	0.44624 (19)	0.7425 (4)	0.0681 (9)
H2	0.5493	0.4900	0.7631	0.082*
C1	0.6480 (4)	0.4351 (2)	0.6160 (4)	0.0718 (9)
H1	0.6168	0.4709	0.5351	0.086*
C11	0.8246 (4)	−0.1018 (2)	0.8043 (4)	0.0895 (11)
H11A	0.7600	−0.0886	0.8652	0.134*
H11B	0.8863	−0.1519	0.8418	0.134*
H11C	0.7633	−0.1144	0.7084	0.134*
C10	1.4150 (4)	0.2024 (3)	0.5989 (5)	0.1034 (14)
H10A	1.4106	0.2562	0.6490	0.155*
H10B	1.4344	0.2147	0.5078	0.155*
H10C	1.4951	0.1663	0.6559	0.155*

	U11	U22	U33	U12	U13	U23
O1	0.0845 (15)	0.0672 (12)	0.0320 (10)	0.0113 (10)	0.0231 (9)	0.0068 (9)
N2	0.0597 (14)	0.0481 (12)	0.0324 (11)	0.0102 (9)	0.0190 (10)	0.0027 (9)
N1	0.0586 (15)	0.0614 (14)	0.0459 (13)	0.0154 (11)	0.0147 (11)	0.0060 (11)
C5	0.0451 (14)	0.0481 (14)	0.0354 (13)	−0.0034 (11)	0.0143 (11)	−0.0020 (11)
C4	0.0429 (14)	0.0483 (14)	0.0377 (13)	0.0000 (11)	0.0113 (11)	−0.0031 (11)
O3	0.0615 (14)	0.0542 (12)	0.1168 (19)	0.0094 (10)	0.0136 (13)	0.0197 (12)
O5	0.0604 (14)	0.1133 (18)	0.0853 (17)	0.0004 (12)	0.0300 (13)	0.0117 (14)
C7	0.0528 (17)	0.0549 (16)	0.0487 (16)	0.0091 (13)	0.0135 (13)	0.0059 (12)
C3	0.0487 (16)	0.0610 (17)	0.0569 (17)	0.0007 (12)	0.0192 (14)	−0.0126 (14)
C6	0.0551 (16)	0.0492 (15)	0.0398 (14)	0.0068 (12)	0.0122 (12)	−0.0003 (11)
C9	0.0544 (18)	0.0568 (17)	0.067 (2)	0.0100 (13)	0.0212 (16)	−0.0023 (15)
C8	0.0487 (16)	0.0591 (16)	0.0548 (17)	0.0081 (12)	0.0122 (13)	−0.0084 (13)
O2	0.0527 (14)	0.0739 (15)	0.156 (3)	0.0068 (11)	0.0223 (15)	0.0351 (14)
O4	0.0874 (19)	0.125 (2)	0.097 (2)	−0.0370 (15)	0.0233 (15)	−0.0456 (16)
C2	0.0446 (17)	0.0597 (18)	0.097 (3)	0.0085 (13)	0.0137 (17)	−0.0148 (17)
C1	0.069 (2)	0.070 (2)	0.073 (2)	0.0214 (16)	0.0127 (17)	0.0125 (17)
C11	0.092 (3)	0.0549 (19)	0.117 (3)	−0.0051 (17)	0.020 (2)	0.0205 (19)
C10	0.057 (2)	0.122 (3)	0.138 (4)	−0.004 (2)	0.038 (2)	0.029 (3)

O1—C5	1.254 (3)	C3—H3	0.9300
N2—C5	1.333 (3)	C6—C8	1.526 (3)
N2—C6	1.447 (3)	C6—H6	0.9800
N2—H2A	0.8600	C9—O4	1.197 (4)
N1—C1	1.343 (3)	C9—C8	1.500 (4)
N1—C4	1.372 (3)	C8—H8A	0.9700
N1—H1A	0.8600	C8—H8B	0.9700
C5—C4	1.451 (3)	C2—C1	1.360 (4)
C4—C3	1.378 (3)	C2—H2	0.9300
O3—C7	1.317 (3)	C1—H1	0.9300
O3—C11	1.452 (4)	C11—H11A	0.9600
O5—C9	1.310 (3)	C11—H11B	0.9600
O5—C10	1.458 (4)	C11—H11C	0.9600
C7—O2	1.179 (3)	C10—H10A	0.9600
C7—C6	1.519 (4)	C10—H10B	0.9600
C3—C2	1.401 (4)	C10—H10C	0.9600
C5—N2—C6	121.4 (2)	O4—C9—C8	123.6 (3)
C5—N2—H2A	119.3	O5—C9—C8	112.7 (3)
C6—N2—H2A	119.3	C9—C8—C6	112.4 (2)
C1—N1—C4	109.5 (2)	C9—C8—H8A	109.1
C1—N1—H1A	125.3	C6—C8—H8A	109.1
C4—N1—H1A	125.3	C9—C8—H8B	109.1
O1—C5—N2	120.4 (2)	C6—C8—H8B	109.1
O1—C5—C4	120.1 (2)	H8A—C8—H8B	107.8
N2—C5—C4	119.5 (2)	C1—C2—C3	107.2 (2)
N1—C4—C3	107.0 (2)	C1—C2—H2	126.4
N1—C4—C5	124.3 (2)	C3—C2—H2	126.4
C3—C4—C5	128.7 (2)	N1—C1—C2	108.9 (3)
C7—O3—C11	117.4 (2)	N1—C1—H1	125.6
C9—O5—C10	116.6 (3)	C2—C1—H1	125.6
O2—C7—O3	123.8 (3)	O3—C11—H11A	109.5
O2—C7—C6	125.1 (2)	O3—C11—H11B	109.5
O3—C7—C6	111.0 (2)	H11A—C11—H11B	109.5
C4—C3—C2	107.5 (3)	O3—C11—H11C	109.5
C4—C3—H3	126.3	H11A—C11—H11C	109.5
C2—C3—H3	126.3	H11B—C11—H11C	109.5
N2—C6—C7	110.6 (2)	O5—C10—H10A	109.5
N2—C6—C8	110.2 (2)	O5—C10—H10B	109.5
C7—C6—C8	112.5 (2)	H10A—C10—H10B	109.5
N2—C6—H6	107.8	O5—C10—H10C	109.5
C7—C6—H6	107.8	H10A—C10—H10C	109.5
C8—C6—H6	107.8	H10B—C10—H10C	109.5
O4—C9—O5	123.7 (3)
C6—N2—C5—O1	5.4 (4)	O2—C7—C6—N2	3.4 (4)
C6—N2—C5—C4	−174.2 (2)	O3—C7—C6—N2	−174.5 (2)
C1—N1—C4—C3	0.5 (3)	O2—C7—C6—C8	−120.3 (3)
C1—N1—C4—C5	177.2 (2)	O3—C7—C6—C8	61.8 (3)
O1—C5—C4—N1	175.5 (2)	C10—O5—C9—O4	1.1 (4)
N2—C5—C4—N1	−4.9 (4)	C10—O5—C9—C8	−176.2 (2)
O1—C5—C4—C3	−8.5 (4)	O4—C9—C8—C6	26.0 (4)
N2—C5—C4—C3	171.0 (2)	O5—C9—C8—C6	−156.8 (2)
C11—O3—C7—O2	3.1 (5)	N2—C6—C8—C9	73.9 (3)
C11—O3—C7—C6	−178.9 (3)	C7—C6—C8—C9	−162.1 (2)
N1—C4—C3—C2	0.2 (3)	C4—C3—C2—C1	−0.8 (3)
C5—C4—C3—C2	−176.3 (2)	C4—N1—C1—C2	−1.0 (3)
C5—N2—C6—C7	76.9 (3)	C3—C2—C1—N1	1.1 (4)
C5—N2—C6—C8	−158.1 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1i	0.86	1.96	2.804 (3)	167
N2—H2A···O1i	0.86	1.99	2.845 (3)	176

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O1i	0.86	1.96	2.804 (3)	167
N2—H2A⋯O1i	0.86	1.99	2.845 (3)	176

Symmetry code: (i) .