2-(4-Chloro-N-{2-[(1H-pyrrol-2-yl)carbon-yloxy]eth-yl}anilino)ethyl 1H-pyrrole-2-carboxyl-ate.

In the title mol-ecule, C(20)H(20)ClN(3)O(4), both the pyrrole N-H groups adopt a syn conformation with respect to the carbonyl groups. In the crystal, inter-molecular N-H⋯O hydrogen bonds link the mol-ecules 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 = 401.84

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.106

S = 1.01

3438 reflections

254 parameters

H-atom parameters constrained

Δρmax = 0.15 e Å−3

Δρmin = −0.24 e Å−3

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.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811056170/cv5220sup1.cif

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

Supplementary material file. DOI: 10.1107/S1600536811056170/cv5220Isup3.cml

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

C20H20ClN3O4	Dx = 1.374 Mg m−3
Mr = 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

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

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(Fo2) + (0.0324P)2 + 0.5658P] where P = (Fo2 + 2Fc2)/3
S = 1.01	(Δ/σ)max < 0.001
3438 reflections	Δρmax = 0.15 e Å−3
254 parameters	Δρmin = −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)

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
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*

	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)

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)

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

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) ; (ii) .