2-(4-Chloro-N-{2-[(1H-pyrrol-2-yl)carbon­yloxy]eth­yl}anilino)ethyl 1H-pyrrole-2-carboxyl­ate

Yan, Y.; Zhang, G.; Yin, Z.

doi:10.1107/S1600536811056170

organic compounds

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ISSN: 2056-9890

Volume 68| Part 2| February 2012| Page o378

doi:10.1107/S1600536811056170

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2-(4-Chloro-N-{2-[(1H-pyrrol-2-yl)carbonyloxy]ethyl}anilino)ethyl 1H-pyrrole-2-carboxylate

Ying Yan,^a Guilong Zhang ^b and Zhenming Yin ^a ^*

^aTianjin Key Laboratory of Structure and Performance for Functional Molecules, College of Chemistry, Tianjin Normal Uinversity, Tianjin 300387, People's Republic of China, and ^bAgro-Environmental Protection Institute, Ministry of Agriculture, Tianjin 300191, People's Republic of China
^*Correspondence e-mail: tjyinzm@yahoo.com.cn

(Received 19 December 2011; accepted 29 December 2011; online 14 January 2012)

In the title molecule, C₂₀H₂₀ClN₃O₄, both the pyrrole N—H groups adopt a syn conformation with respect to the carbonyl groups. In the crystal, intermolecular N—H⋯O hydrogen bonds link the molecules into layers parallel to (102).

Related literature

For the crystal structures of related pyrrole-2-carboxylate derivatives, see: Sessler et al. (2003 ); Yin & Li (2006 ); Maeda et al. (2007 ); Cui et al. (2009 ).

Experimental

Crystal data

C₂₀H₂₀ClN₃O₄
M_r = 401.84
Monoclinic, P 2₁ /c
a = 19.972 (2) Å
b = 4.7426 (5) Å
c = 20.613 (2) Å
β = 95.815 (2)°
V = 1942.4 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.23 mm⁻¹
T = 296 K
0.28 × 0.20 × 0.18 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 1999 ) T_min = 0.488, T_max = 1.000
9198 measured reflections
3438 independent reflections
1763 reflections with I > 2σ(I)
R_int = 0.046

Refinement

R[F² > 2σ(F²)] = 0.038
wR(F²) = 0.106
S = 1.01
3438 reflections
254 parameters
H-atom parameters constrained
Δρ_max = 0.15 e Å⁻³
Δρ_min = −0.24 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1ⁱ	0.86	2.07	2.893 (3)	160
N3—H3⋯O4ⁱⁱ	0.86	2.07	2.891 (3)	158
Symmetry codes: (i) -x+1, -y+3, -z+1; (ii) $[-x, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 1999); cell refinement: SAINT (Bruker, 1999); 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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811056170/cv5220sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811056170/cv5220Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811056170/cv5220Isup3.cml

checkCIF report

Comment top

The use of 2-carbonyl-functionalized pyrrole moieties as building blocks to create hydrogen bonded self-assembled aggregates has received some attention recently (Sessler et al., 2003; Yin et al. 2006; Maeda et al. 2007). In continuation of our study of the solid state self-assemblies of some pyrrole-2-carboxylate compounds (Cui et al. 2009), we report the crystal structure of the title compound, (I).

In (I) (Fig. 1), both the pyrrole NH groups adopt syn conformation with respect to the carbonyl groups. The molecules of the title compound self-assemble into one-dimensional tape through helical N—H···O hydrogen bonds (Table 1). Further, intermolecular N—H···O hydrogen bonds (Table 1) link these tapes into layers parallel to (102) plane. The hydrogen bonding motif in the crystal of (I) is different from that reported for N,N-di[2- (1H-pyrrole-2-carbonyloxy)ethyl]-aniline (Cui et al., 2009). Apparently, the chloro group has great influence on the crystal packing.

Related literature top

For the crystal structures of related pyrrole-2-carboxylate derivatives, see: Sessler et al. (2003); Yin & Li (2006), Maeda et al. (2007); Cui et al. (2009).

Experimental top

N,N-Di(2-hydroxyethyl)-4-chloroaniline (0.215 g), 2-(trichloroacetyl)-1H-pyrrole(0.59 g) and triethylamine (1 mL) were added to acetonitrile (15 ml), and the mixture was refluxed for 10 h. The solution was then evaporated under reduced pressure and the residue was purified by column chromatography on silica gel with ethyl acetate-petroleum ether (1:4 v/v), affording the title compound.

Computing details top

Data collection: SMART (Bruker, 1999); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT (Bruker, 1999); 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 (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of (I), with the atom-numbering scheme and 30% probability displacement ellipsoids.

2-(4-Chloro-N-{2-[(1H-pyrrol-2- yl)carbonyloxy]ethyl}anilino)ethyl 1H-pyrrole-2-carboxylate top

Crystal data top

C₂₀H₂₀ClN₃O₄	D_x = 1.374 Mg m⁻³
M_r = 401.84	Melting point: 438 K
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 19.972 (2) Å	Cell parameters from 1561 reflections
b = 4.7426 (5) Å	θ = 2.7–21.7°
c = 20.613 (2) Å	µ = 0.23 mm⁻¹
β = 95.815 (2)°	T = 296 K
V = 1942.4 (4) Å³	Block, yellow
Z = 4	0.28 × 0.20 × 0.18 mm
F(000) = 840

Data collection top

Bruker SMART CCD area-detector diffractometer	3438 independent reflections
Radiation source: fine-focus sealed tube	1763 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.046
phi and ω scans	θ_max = 25.0°, θ_min = 1.0°
Absorption correction: multi-scan (SADABS; Bruker, 1999)	h = −23→23
T_min = 0.488, T_max = 1.000	k = −5→5
9198 measured reflections	l = −24→13

Refinement top

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)] = 0.038	H-atom parameters constrained
wR(F²) = 0.106	w = 1/[σ²(F_o²) + (0.0324P)² + 0.5658P] where P = (F_o² + 2F_c²)/3
S = 1.01	(Δ/σ)_max < 0.001
3438 reflections	Δρ_max = 0.15 e Å⁻³
254 parameters	Δρ_min = −0.24 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0036 (6)

Crystal data top

C₂₀H₂₀ClN₃O₄	V = 1942.4 (4) Å³
M_r = 401.84	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 19.972 (2) Å	µ = 0.23 mm⁻¹
b = 4.7426 (5) Å	T = 296 K
c = 20.613 (2) Å	0.28 × 0.20 × 0.18 mm
β = 95.815 (2)°

Data collection top

Bruker SMART CCD area-detector diffractometer	3438 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 1999)	1763 reflections with I > 2σ(I)
T_min = 0.488, T_max = 1.000	R_int = 0.046
9198 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.038	0 restraints
wR(F²) = 0.106	H-atom parameters constrained
S = 1.01	Δρ_max = 0.15 e Å⁻³
3438 reflections	Δρ_min = −0.24 e Å⁻³
254 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Cl1	0.28670 (5)	0.3365 (2)	0.13385 (4)	0.0869 (4)
O1	0.42313 (10)	1.2588 (4)	0.50098 (10)	0.0631 (6)
O2	0.37700 (9)	0.9028 (4)	0.43966 (8)	0.0556 (6)
O3	0.06269 (9)	0.9926 (4)	0.41172 (8)	0.0526 (5)
O4	0.05353 (10)	1.1201 (5)	0.30620 (8)	0.0639 (6)
N1	0.51710 (12)	1.3321 (5)	0.40646 (11)	0.0548 (6)
H1	0.5250	1.4524	0.4375	0.066*
N2	0.23923 (11)	0.7752 (5)	0.39523 (11)	0.0527 (7)
N3	−0.05067 (11)	1.4950 (5)	0.33134 (10)	0.0529 (7)
H3	−0.0412	1.5110	0.2917	0.063*
C1	0.55231 (16)	1.3079 (7)	0.35432 (15)	0.0637 (9)
H1A	0.5892	1.4169	0.3462	0.076*
C2	0.52445 (16)	1.0957 (7)	0.31537 (15)	0.0642 (9)
H2	0.5388	1.0351	0.2761	0.077*
C3	0.47069 (15)	0.9876 (7)	0.34556 (14)	0.0561 (8)
H3A	0.4424	0.8414	0.3301	0.067*
C4	0.46687 (14)	1.1355 (6)	0.40230 (13)	0.0464 (7)
C5	0.42220 (14)	1.1110 (7)	0.45249 (14)	0.0472 (7)
C6	0.32809 (13)	0.8638 (7)	0.48606 (12)	0.0538 (8)
H6A	0.3082	1.0432	0.4961	0.065*
H6B	0.3494	0.7831	0.5262	0.065*
C7	0.27484 (14)	0.6671 (6)	0.45514 (13)	0.0541 (8)
H7A	0.2958	0.4891	0.4458	0.065*
H7B	0.2425	0.6301	0.4862	0.065*
C8	0.25169 (13)	0.6761 (6)	0.33371 (13)	0.0469 (7)
C9	0.30389 (14)	0.4884 (7)	0.32549 (14)	0.0570 (8)
H9	0.3324	0.4320	0.3616	0.068*
C10	0.31402 (15)	0.3851 (7)	0.26484 (16)	0.0645 (9)
H10	0.3481	0.2547	0.2607	0.077*
C11	0.27436 (16)	0.4726 (7)	0.21056 (14)	0.0575 (8)
C12	0.22420 (15)	0.6637 (7)	0.21674 (14)	0.0600 (9)
H12	0.1978	0.7265	0.1798	0.072*
C13	0.21230 (14)	0.7647 (7)	0.27770 (14)	0.0556 (8)
H13	0.1776	0.8930	0.2812	0.067*
C14	0.18334 (13)	0.9640 (6)	0.40279 (13)	0.0529 (8)
H14A	0.1808	1.1052	0.3686	0.063*
H14B	0.1910	1.0604	0.4444	0.063*
C15	0.11705 (13)	0.8046 (6)	0.39957 (14)	0.0530 (8)
H15A	0.1076	0.7194	0.3568	0.064*
H15B	0.1204	0.6548	0.4318	0.064*
C16	0.03441 (14)	1.1389 (6)	0.36010 (13)	0.0461 (7)
C17	−0.01934 (13)	1.3157 (6)	0.37684 (12)	0.0423 (7)
C18	−0.04881 (14)	1.3549 (6)	0.43337 (13)	0.0534 (8)
H18	−0.0375	1.2621	0.4727	0.064*
C19	−0.09868 (15)	1.5583 (7)	0.42135 (15)	0.0643 (9)
H19	−0.1270	1.6252	0.4510	0.077*
C20	−0.09841 (15)	1.6418 (7)	0.35789 (15)	0.0623 (9)
H20	−0.1265	1.7770	0.3368	0.075*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0873 (7)	0.1160 (8)	0.0615 (5)	0.0033 (6)	0.0274 (5)	−0.0115 (5)
O1	0.0676 (14)	0.0668 (15)	0.0543 (12)	−0.0081 (12)	0.0035 (10)	−0.0143 (12)
O2	0.0497 (12)	0.0689 (15)	0.0488 (12)	−0.0128 (12)	0.0084 (9)	−0.0084 (11)
O3	0.0464 (12)	0.0692 (14)	0.0436 (11)	0.0102 (11)	0.0116 (9)	0.0052 (11)
O4	0.0646 (13)	0.0917 (17)	0.0371 (11)	0.0102 (13)	0.0130 (10)	−0.0033 (11)
N1	0.0536 (15)	0.0539 (16)	0.0562 (15)	−0.0041 (14)	0.0022 (12)	−0.0013 (13)
N2	0.0418 (14)	0.0638 (18)	0.0517 (15)	0.0093 (13)	0.0004 (12)	0.0011 (13)
N3	0.0504 (15)	0.0690 (18)	0.0393 (13)	−0.0003 (14)	0.0051 (12)	0.0025 (13)
C1	0.057 (2)	0.070 (2)	0.065 (2)	−0.0030 (19)	0.0110 (17)	0.011 (2)
C2	0.066 (2)	0.073 (3)	0.0548 (19)	0.000 (2)	0.0137 (17)	−0.0007 (19)
C3	0.056 (2)	0.060 (2)	0.0521 (18)	−0.0013 (18)	0.0028 (15)	0.0004 (17)
C4	0.0407 (17)	0.048 (2)	0.0491 (18)	−0.0010 (16)	−0.0021 (14)	0.0025 (16)
C5	0.0410 (18)	0.050 (2)	0.0480 (18)	0.0039 (16)	−0.0082 (14)	0.0029 (16)
C6	0.0490 (18)	0.069 (2)	0.0436 (17)	−0.0018 (17)	0.0064 (14)	0.0031 (16)
C7	0.0493 (18)	0.060 (2)	0.0545 (18)	−0.0017 (17)	0.0110 (15)	0.0118 (16)
C8	0.0389 (17)	0.051 (2)	0.0515 (18)	−0.0034 (16)	0.0086 (14)	0.0023 (16)
C9	0.0475 (19)	0.068 (2)	0.0551 (19)	0.0104 (17)	0.0031 (15)	0.0016 (17)
C10	0.054 (2)	0.069 (2)	0.073 (2)	0.0122 (19)	0.0160 (17)	0.000 (2)
C11	0.054 (2)	0.068 (2)	0.0529 (19)	−0.0033 (19)	0.0168 (16)	0.0008 (18)
C12	0.056 (2)	0.072 (2)	0.0517 (19)	0.0008 (19)	0.0040 (15)	0.0119 (18)
C13	0.0483 (18)	0.062 (2)	0.0566 (19)	0.0061 (16)	0.0055 (15)	0.0055 (17)
C14	0.0424 (18)	0.059 (2)	0.0574 (18)	0.0011 (17)	0.0052 (14)	−0.0062 (16)
C15	0.0446 (18)	0.056 (2)	0.0594 (18)	0.0049 (17)	0.0116 (14)	0.0029 (16)
C16	0.0433 (17)	0.057 (2)	0.0384 (17)	−0.0065 (16)	0.0047 (14)	−0.0002 (16)
C17	0.0409 (16)	0.0530 (19)	0.0324 (14)	0.0004 (15)	0.0010 (12)	0.0011 (14)
C18	0.0558 (19)	0.065 (2)	0.0404 (16)	0.0045 (18)	0.0113 (14)	0.0016 (16)
C19	0.062 (2)	0.075 (3)	0.058 (2)	0.013 (2)	0.0159 (17)	−0.0068 (18)
C20	0.053 (2)	0.065 (2)	0.067 (2)	0.0095 (18)	0.0005 (17)	0.0014 (19)

Geometric parameters (Å, º) top

Cl1—C11	1.748 (3)	C6—H6B	0.9700
O1—C5	1.219 (3)	C7—H7A	0.9700
O2—C5	1.346 (3)	C7—H7B	0.9700
O2—C6	1.447 (3)	C8—C9	1.394 (4)
O3—C16	1.345 (3)	C8—C13	1.395 (4)
O3—C15	1.446 (3)	C9—C10	1.377 (4)
O4—C16	1.214 (3)	C9—H9	0.9300
N1—C1	1.347 (3)	C10—C11	1.368 (4)
N1—C4	1.366 (3)	C10—H10	0.9300
N1—H1	0.8600	C11—C12	1.366 (4)
N2—C8	1.398 (3)	C12—C13	1.387 (4)
N2—C14	1.452 (3)	C12—H12	0.9300
N2—C7	1.455 (3)	C13—H13	0.9300
N3—C20	1.341 (3)	C14—C15	1.520 (4)
N3—C17	1.370 (3)	C14—H14A	0.9700
N3—H3	0.8600	C14—H14B	0.9700
C1—C2	1.370 (4)	C15—H15A	0.9700
C1—H1A	0.9300	C15—H15B	0.9700
C2—C3	1.392 (4)	C16—C17	1.432 (4)
C2—H2	0.9300	C17—C18	1.370 (3)
C3—C4	1.372 (4)	C18—C19	1.391 (4)
C3—H3A	0.9300	C18—H18	0.9300
C4—C5	1.438 (4)	C19—C20	1.367 (4)
C6—C7	1.507 (4)	C19—H19	0.9300
C6—H6A	0.9700	C20—H20	0.9300

C5—O2—C6	116.6 (2)	C10—C9—H9	119.4
C16—O3—C15	116.3 (2)	C8—C9—H9	119.4
C1—N1—C4	109.3 (3)	C11—C10—C9	120.6 (3)
C1—N1—H1	125.3	C11—C10—H10	119.7
C4—N1—H1	125.3	C9—C10—H10	119.7
C8—N2—C14	120.9 (2)	C12—C11—C10	119.6 (3)
C8—N2—C7	122.3 (2)	C12—C11—Cl1	120.1 (2)
C14—N2—C7	116.2 (2)	C10—C11—Cl1	120.3 (3)
C20—N3—C17	109.7 (2)	C11—C12—C13	120.5 (3)
C20—N3—H3	125.1	C11—C12—H12	119.7
C17—N3—H3	125.1	C13—C12—H12	119.7
N1—C1—C2	108.4 (3)	C12—C13—C8	120.8 (3)
N1—C1—H1A	125.8	C12—C13—H13	119.6
C2—C1—H1A	125.8	C8—C13—H13	119.6
C1—C2—C3	107.1 (3)	N2—C14—C15	111.4 (2)
C1—C2—H2	126.4	N2—C14—H14A	109.4
C3—C2—H2	126.4	C15—C14—H14A	109.4
C4—C3—C2	107.7 (3)	N2—C14—H14B	109.4
C4—C3—H3A	126.1	C15—C14—H14B	109.4
C2—C3—H3A	126.1	H14A—C14—H14B	108.0
N1—C4—C3	107.4 (3)	O3—C15—C14	110.6 (2)
N1—C4—C5	121.0 (3)	O3—C15—H15A	109.5
C3—C4—C5	131.6 (3)	C14—C15—H15A	109.5
O1—C5—O2	122.5 (3)	O3—C15—H15B	109.5
O1—C5—C4	125.7 (3)	C14—C15—H15B	109.5
O2—C5—C4	111.8 (3)	H15A—C15—H15B	108.1
O2—C6—C7	107.1 (2)	O4—C16—O3	122.7 (3)
O2—C6—H6A	110.3	O4—C16—C17	125.2 (3)
C7—C6—H6A	110.3	O3—C16—C17	112.1 (2)
O2—C6—H6B	110.3	N3—C17—C18	107.0 (3)
C7—C6—H6B	110.3	N3—C17—C16	120.0 (2)
H6A—C6—H6B	108.5	C18—C17—C16	133.0 (3)
N2—C7—C6	113.8 (2)	C17—C18—C19	107.7 (3)
N2—C7—H7A	108.8	C17—C18—H18	126.1
C6—C7—H7A	108.8	C19—C18—H18	126.1
N2—C7—H7B	108.8	C20—C19—C18	107.4 (3)
C6—C7—H7B	108.8	C20—C19—H19	126.3
H7A—C7—H7B	107.7	C18—C19—H19	126.3
C9—C8—C13	117.3 (3)	N3—C20—C19	108.2 (3)
C9—C8—N2	121.9 (3)	N3—C20—H20	125.9
C13—C8—N2	120.8 (3)	C19—C20—H20	125.9
C10—C9—C8	121.2 (3)

C4—N1—C1—C2	0.6 (3)	C9—C10—C11—C12	−0.2 (5)
N1—C1—C2—C3	−0.3 (3)	C9—C10—C11—Cl1	−179.0 (2)
C1—C2—C3—C4	−0.1 (3)	C10—C11—C12—C13	−1.4 (5)
C1—N1—C4—C3	−0.7 (3)	Cl1—C11—C12—C13	177.5 (2)
C1—N1—C4—C5	178.8 (3)	C11—C12—C13—C8	0.7 (5)
C2—C3—C4—N1	0.5 (3)	C9—C8—C13—C12	1.4 (4)
C2—C3—C4—C5	−178.9 (3)	N2—C8—C13—C12	−179.2 (3)
C6—O2—C5—O1	0.9 (4)	C8—N2—C14—C15	78.5 (3)
C6—O2—C5—C4	−178.3 (2)	C7—N2—C14—C15	−93.4 (3)
N1—C4—C5—O1	1.7 (4)	C16—O3—C15—C14	84.3 (3)
C3—C4—C5—O1	−179.0 (3)	N2—C14—C15—O3	176.0 (2)
N1—C4—C5—O2	−179.1 (2)	C15—O3—C16—O4	−1.2 (4)
C3—C4—C5—O2	0.2 (4)	C15—O3—C16—C17	179.2 (2)
C5—O2—C6—C7	168.1 (2)	C20—N3—C17—C18	−0.2 (3)
C8—N2—C7—C6	104.4 (3)	C20—N3—C17—C16	−179.1 (3)
C14—N2—C7—C6	−83.8 (3)	O4—C16—C17—N3	−4.3 (4)
O2—C6—C7—N2	−61.2 (3)	O3—C16—C17—N3	175.3 (2)
C14—N2—C8—C9	−178.2 (3)	O4—C16—C17—C18	177.1 (3)
C7—N2—C8—C9	−6.8 (4)	O3—C16—C17—C18	−3.3 (4)
C14—N2—C8—C13	2.5 (4)	N3—C17—C18—C19	0.5 (3)
C7—N2—C8—C13	173.8 (3)	C16—C17—C18—C19	179.2 (3)
C13—C8—C9—C10	−3.0 (4)	C17—C18—C19—C20	−0.6 (4)
N2—C8—C9—C10	177.7 (3)	C17—N3—C20—C19	−0.1 (3)
C8—C9—C10—C11	2.4 (5)	C18—C19—C20—N3	0.4 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1ⁱ	0.86	2.07	2.893 (3)	160
N3—H3···O4ⁱⁱ	0.86	2.07	2.891 (3)	158

Symmetry codes: (i) −x+1, −y+3, −z+1; (ii) −x, y+1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₂₀H₂₀ClN₃O₄
M_r	401.84
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	19.972 (2), 4.7426 (5), 20.613 (2)
β (°)	95.815 (2)
V (Å³)	1942.4 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.23
Crystal size (mm)	0.28 × 0.20 × 0.18

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 1999)
T_min, T_max	0.488, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	9198, 3438, 1763
R_int	0.046
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.038, 0.106, 1.01
No. of reflections	3438
No. of parameters	254
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.15, −0.24

Computer programs: SMART (Bruker, 1999), SAINT (Bruker, 1999), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1ⁱ	0.86	2.07	2.893 (3)	160
N3—H3···O4ⁱⁱ	0.86	2.07	2.891 (3)	158

Symmetry codes: (i) −x+1, −y+3, −z+1; (ii) −x, y+1/2, −z+1/2.

Acknowledgements

We sincerely thank the Natural Science Foundation of China for financial support from the (NSFC grant Nos. 21172174 and 20702038).

References

Bruker (1999). SADABS, SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Cui, Y., Yin, Z., Dong, L. & He, J. (2009). J. Mol. Struct. 938, 322–327. Web of Science CSD CrossRef CAS Google Scholar
Maeda, H., Kusunose, Y., Terasaki, M., Ito, Y., Fujimoto, C., Fujii, R. & Nakanishi, T. (2007). Chem. Asian J. 2, 350–357. Web of Science CSD CrossRef PubMed CAS Google Scholar
Sessler, J. L., Berthon-Gelloz, G., Gale, P. A., Camiolo, S., Anslyn, E. V., Anzenbacher, P. Jr, Furuta, H., Kirkovits, G. J., Lynch, V. M., Maeda, H., Morosini, P., Scherer, M., Shriver, J. & Zimmerman, R. S. (2003). Polyhedron, 22, 2963–2983. Web of Science CSD CrossRef CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Yin, Z. & Li, Z. (2006). Tetrahedron Lett. 47, 7875–7879. Web of Science CSD CrossRef CAS Google Scholar

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Volume 68| Part 2| February 2012| Page o378

doi:10.1107/S1600536811056170

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

2-(4-Chloro-N-{2-[(1H-pyrrol-2-yl)carbon­yl­oxy]eth­yl}anilino)ethyl 1H-pyrrole-2-carboxyl­ate

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

2-(4-Chloro-N-{2-[(1H-pyrrol-2-yl)carbonyloxy]ethyl}anilino)ethyl 1H-pyrrole-2-carboxylate