Ethyl 5-cyano-4-[2-(2,4-dichloro­phen­oxy)acetamido]-1-phenyl-1H-pyrrole-3-carboxyl­ate

Xu, J.; Sheng, H.; He, M.; He, P.

doi:10.1107/S1600536809027809

organic compounds

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ISSN: 2056-9890

Volume 65| Part 8| August 2009| Page o1950

doi:10.1107/S1600536809027809

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Ethyl 5-cyano-4-[2-(2,4-dichlorophenoxy)acetamido]-1-phenyl-1H-pyrrole-3-carboxylate

Jing Xu,^a ^* Hui Sheng,^b Mei He ^c and Ping He ^d

^aInstitute of Medicinal Chemistry, Yunyang Medical College, Shiyan 442000, People's Republic of China, ^bSchool of Basic Medical Science, Yunyang Medical College and Yunyang Medical College Library, Shiyan 442000, People's Republic of China, ^cDepartment of Pharmacy, Affiliated Renmin Hospital, Yunyang Medical College, Shiyan 442000, People's Republic of China, and ^dKey Laboratory of Pesticides & Chemical Biology, Ministry of Education, Central China Normal University, Wuhan 430079, People's Republic of China
^*Correspondence e-mail: jxu6686@yahoo.com.cn

(Received 9 July 2009; accepted 15 July 2009; online 22 July 2009)

In the title compound, C₂₂H₁₇Cl₂N₃O₄, the pyrrole ring and the 2,4-dichlorophenyl group form a dihedral angle of 8.14 (13)°; the phenyl ring is twisted with respect to the pyrrole ring, forming a dihedral angle of 60.77 (14)°. The C=O bond length is 1.213 (3) Å, indicating that the molecule is in the keto form, associated with a –CONH– group, and the amide group adopts the usual trans conformation. The molecule is stabilized by an intramolecular N—H⋯O hydrogen-bonding interaction. In the crystal, the stacked molecules exhibit intermolecular C—H⋯O and C—H⋯N hydrogen-bonding interactions.

Related literature

For the preparation and biological activity of acid amides, see: Xue et al. (2007 ); Li et al. (1995 ). For related structures, see: He et al. (2007a ,b ).

Experimental

Crystal data

C₂₂H₁₇Cl₂N₃O₄
M_r = 458.29
Monoclinic, C 2/c
a = 32.8846 (18) Å
b = 7.6224 (4) Å
c = 17.2834 (9) Å
γ = 89.773 (1)°
V = 4332.2 (4) Å³
Z = 8
Mo Kα radiation
μ = 0.33 mm⁻¹
T = 298 K
0.10 × 0.10 × 0.10 mm

Data collection

Bruker SMART 4K CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2003 ) T_min = 0.968, T_max = 0.968
16521 measured reflections
4279 independent reflections
3034 reflections with I > 2σ(I)
R_int = 0.081

Refinement

R[F² > 2σ(F²)] = 0.066
wR(F²) = 0.154
S = 0.99
4279 reflections
285 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.32 e Å⁻³
Δρ_min = −0.31 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O3	0.82 (2)	2.15 (3)	2.813 (3)	137 (2)
C7—H7A⋯O2ⁱ	0.97	2.57	3.341 (3)	137
C3—H3⋯N3ⁱ	0.93	2.61	3.312 (3)	133
Symmetry code: (i) $[-x+2, y, -z+{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 2001 ); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009 ); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809027809/at2840sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809027809/at2840Isup2.hkl

checkCIF report

Comment top

The chemical and pharmacological properties of acid amides have been investigated extensively, owing to their potentially beneficial chemical and biological activties (Xue et al., 2007 and Li et al., 1995). As part of our studies on the synthesis and characterization of related compounds (He et al., 2007a,b), we report here the synthesis and crystal structure of ethyl 4-(2-(2,4-dichlorophenoxy)acetamido)-5-cyano-1-phenyl-1H-pyrrole- 3-carboxylate, (I).

Within the molecule of (I), the bond lengths and angles present no unusual features. The pyrrole ring and the 2,4-dichlorophenyl group form a dihedral angle of 8.14 (13)°, the C17—C22 phenyl ring is twisted with respect to pyrrole ring, with a dihedral angle of 60.77 (14)°. The C=O bond length is 1.213 (3) Å, indicating that the molecule is in the keto form (Fig. 1), associated with –CONH– moiety, and the amide group adopts the usual trans conformation. The crystal structure is stabilized by intramolecular N—H···O hydrogen bonds interactions. In additional, the stacked molecules exhibit intermolecular C—H···O and C—H···N hydrogen bonds interactions (Fig 2. Table 1).

Related literature top

For the preparation and biological activity of acid amides, see: Xue et al. (2007); Li et al. (1995). For related structures, see: He et al. (2007a,b).

Experimental top

To a solution of the ethyl 4-amino-5-cyano-1-phenyl-1H-pyrrole-3-carboxylate (3 mmol) in dry dichloromethane (15 ml) was added 2-(2,4-dichlorophenoxy)acetyl chloride at 273–278 K. After stirring the reaction mixture for 4 h from 273–278 K to room temperature. The solution was concentrated under reduced pressure and the residue was recrystallized from ethanol to give the title compound in a yield of 45%. Crystals suitable for single-crystal X-ray diffraction were obtained by recrystallization from a mixed solvent of ethanol and dichloromethane (1:3 v/v) at room temperature.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. A view of the molecule of (I) showing the atom-labeling scheme. Displacement ellipsoids are drawn at the 50% probability level. Intramolecular hydrogen bonds are drawn as a dashed line.
	Fig. 2. Part of the crystal structure of (I), showing hydrogen bonds stacking interactions.

Ethyl 5-cyano-4-[2-(2,4-dichlorophenoxy)acetamido]-1-phenyl-1H-pyrrole- 3-carboxylate top

Crystal data top

C₂₂H₁₇Cl₂N₃O₄	F(000) = 1888
M_r = 458.29	D_x = 1.401 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 4400 reflections
a = 32.8846 (18) Å	θ = 2.5–26.3°
b = 7.6224 (4) Å	µ = 0.33 mm⁻¹
c = 17.2834 (9) Å	T = 298 K
β = 90°	Block, yellow
V = 4332.2 (4) Å³	0.10 × 0.10 × 0.10 mm
Z = 8

Data collection top

Bruker SMART 4K CCD area-detector diffractometer	4279 independent reflections
Radiation source: fine-focus sealed tube	3034 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.081
ϕ and ω scans	θ_max = 26.0°, θ_min = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	h = −40→39
T_min = 0.968, T_max = 0.968	k = −9→9
16521 measured reflections	l = −21→21

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)] = 0.066	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.154	w = 1/[σ²(F_o²) + (0.055P)²] where P = (F_o² + 2F_c²)/3
S = 0.99	(Δ/σ)_max = 0.001
4279 reflections	Δρ_max = 0.32 e Å⁻³
285 parameters	Δρ_min = −0.31 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: 0.0042 (4)

Crystal data top

C₂₂H₁₇Cl₂N₃O₄	V = 4332.2 (4) Å³
M_r = 458.29	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 32.8846 (18) Å	µ = 0.33 mm⁻¹
b = 7.6224 (4) Å	T = 298 K
c = 17.2834 (9) Å	0.10 × 0.10 × 0.10 mm
β = 90°

Data collection top

Bruker SMART 4K CCD area-detector diffractometer	4279 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	3034 reflections with I > 2σ(I)
T_min = 0.968, T_max = 0.968	R_int = 0.081
16521 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.066	0 restraints
wR(F²) = 0.154	H atoms treated by a mixture of independent and constrained refinement
S = 0.99	Δρ_max = 0.32 e Å⁻³
4279 reflections	Δρ_min = −0.31 e Å⁻³
285 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
C1	1.06329 (6)	0.1879 (3)	0.05715 (13)	0.0426 (6)
C2	1.09068 (7)	0.1312 (3)	0.11185 (14)	0.0466 (6)
H2	1.0813	0.0801	0.1573	0.056*
C3	1.13204 (7)	0.1495 (3)	0.09995 (14)	0.0472 (6)
H3	1.1505	0.1107	0.1369	0.057*
C4	1.14550 (7)	0.2257 (3)	0.03284 (15)	0.0463 (6)
C5	1.11863 (7)	0.2840 (3)	−0.02255 (14)	0.0470 (6)
H5	1.1282	0.3351	−0.0679	0.056*
C6	1.07783 (7)	0.2659 (3)	−0.01021 (14)	0.0469 (6)
C7	1.00695 (6)	0.1112 (4)	0.13490 (13)	0.0558 (7)
H7A	1.0184	0.1792	0.1770	0.067*
H7B	1.0147	−0.0103	0.1420	0.067*
C8	0.96114 (7)	0.1270 (4)	0.13558 (14)	0.0511 (7)
C9	0.90125 (6)	0.1809 (3)	0.05703 (13)	0.0368 (5)
C10	0.88509 (6)	0.2629 (3)	−0.00962 (13)	0.0399 (6)
C11	0.84392 (7)	0.2760 (3)	0.00079 (14)	0.0440 (6)
H11	0.8259	0.3266	−0.0340	0.053*
C12	0.86902 (6)	0.1425 (3)	0.10524 (12)	0.0387 (5)
C13	0.86531 (6)	0.0454 (3)	0.17456 (14)	0.0446 (6)
C14	0.90849 (7)	0.3115 (3)	−0.07786 (13)	0.0431 (6)
C15	0.90645 (8)	0.4263 (4)	−0.20453 (14)	0.0589 (7)
H15A	0.9189	0.3226	−0.2267	0.071*
H15B	0.9277	0.5115	−0.1943	0.071*
C16	0.87619 (9)	0.5007 (4)	−0.25914 (15)	0.0693 (8)
H16A	0.8568	0.4119	−0.2729	0.104*
H16B	0.8898	0.5412	−0.3048	0.104*
H16C	0.8624	0.5970	−0.2350	0.104*
C17	0.79429 (7)	0.2161 (4)	0.10469 (13)	0.0448 (6)
C18	0.77391 (8)	0.0684 (4)	0.12715 (16)	0.0647 (8)
H18	0.7852	−0.0419	0.1193	0.078*
C19	0.73596 (8)	0.0858 (5)	0.16203 (18)	0.0770 (10)
H19	0.7217	−0.0133	0.1775	0.092*
C20	0.71982 (8)	0.2485 (5)	0.17348 (18)	0.0729 (10)
H20	0.6945	0.2596	0.1968	0.088*
C21	0.74032 (9)	0.3942 (5)	0.15128 (18)	0.0774 (10)
H21	0.7291	0.5045	0.1596	0.093*
C22	0.77795 (8)	0.3792 (4)	0.11624 (16)	0.0650 (8)
H22	0.7920	0.4789	0.1007	0.078*
Cl1	1.197500 (19)	0.25261 (10)	0.01853 (5)	0.0708 (3)
Cl2	1.04355 (2)	0.33930 (11)	−0.07912 (4)	0.0718 (3)
N1	0.94269 (5)	0.1515 (3)	0.06772 (11)	0.0413 (5)
H1	0.9550 (7)	0.163 (3)	0.0265 (14)	0.050*
N2	0.83373 (5)	0.2042 (3)	0.06907 (11)	0.0428 (5)
N3	0.85896 (7)	−0.0374 (3)	0.22814 (13)	0.0672 (7)
O1	1.02216 (4)	0.1736 (3)	0.06353 (9)	0.0548 (5)
O2	0.94335 (5)	0.1152 (3)	0.19676 (10)	0.0876 (8)
O3	0.94465 (5)	0.2865 (3)	−0.08352 (10)	0.0602 (5)
O4	0.88571 (5)	0.3817 (2)	−0.13360 (9)	0.0512 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0333 (11)	0.0469 (14)	0.0477 (14)	−0.0048 (11)	0.0088 (9)	−0.0098 (11)
C2	0.0392 (12)	0.0525 (16)	0.0481 (14)	0.0005 (11)	0.0085 (10)	−0.0034 (11)
C3	0.0365 (12)	0.0482 (15)	0.0568 (15)	−0.0009 (11)	0.0050 (10)	−0.0051 (12)
C4	0.0351 (12)	0.0420 (15)	0.0619 (17)	−0.0056 (10)	0.0123 (11)	−0.0102 (12)
C5	0.0456 (14)	0.0446 (15)	0.0509 (15)	−0.0098 (12)	0.0122 (11)	−0.0045 (12)
C6	0.0453 (13)	0.0466 (15)	0.0488 (15)	−0.0050 (11)	0.0058 (11)	−0.0047 (11)
C7	0.0332 (12)	0.088 (2)	0.0467 (15)	−0.0018 (13)	0.0080 (10)	0.0048 (14)
C8	0.0367 (12)	0.0704 (19)	0.0462 (15)	−0.0007 (12)	0.0077 (10)	0.0003 (13)
C9	0.0346 (11)	0.0349 (12)	0.0408 (13)	0.0005 (9)	0.0069 (9)	−0.0042 (10)
C10	0.0379 (12)	0.0401 (14)	0.0417 (13)	−0.0004 (10)	0.0061 (9)	−0.0062 (10)
C11	0.0402 (12)	0.0495 (15)	0.0422 (14)	0.0065 (11)	0.0030 (10)	0.0003 (11)
C12	0.0335 (11)	0.0396 (14)	0.0429 (13)	0.0006 (10)	0.0037 (9)	−0.0053 (10)
C13	0.0387 (12)	0.0448 (15)	0.0503 (15)	−0.0017 (11)	0.0095 (10)	−0.0015 (12)
C14	0.0451 (13)	0.0406 (14)	0.0438 (14)	−0.0024 (11)	0.0071 (10)	−0.0033 (11)
C15	0.0665 (16)	0.0642 (19)	0.0462 (15)	−0.0044 (14)	0.0142 (12)	0.0064 (13)
C16	0.095 (2)	0.0593 (19)	0.0532 (17)	0.0005 (16)	0.0097 (15)	0.0086 (14)
C17	0.0321 (11)	0.0607 (17)	0.0417 (14)	0.0026 (11)	0.0075 (9)	−0.0056 (12)
C18	0.0486 (15)	0.062 (2)	0.083 (2)	−0.0056 (14)	0.0190 (13)	−0.0104 (16)
C19	0.0512 (16)	0.090 (3)	0.089 (2)	−0.0172 (17)	0.0248 (15)	−0.0068 (19)
C20	0.0404 (15)	0.113 (3)	0.065 (2)	0.0102 (17)	0.0119 (13)	−0.0050 (18)
C21	0.0597 (18)	0.076 (2)	0.097 (2)	0.0263 (17)	0.0216 (16)	0.0000 (19)
C22	0.0525 (15)	0.062 (2)	0.081 (2)	0.0180 (14)	0.0167 (14)	0.0102 (15)
Cl1	0.0377 (4)	0.0833 (7)	0.0914 (6)	−0.0088 (3)	0.0170 (3)	0.0030 (4)
Cl2	0.0563 (4)	0.0931 (7)	0.0661 (5)	−0.0070 (4)	−0.0030 (3)	0.0237 (4)
N1	0.0296 (9)	0.0548 (13)	0.0395 (11)	0.0012 (9)	0.0095 (8)	−0.0021 (9)
N2	0.0327 (10)	0.0500 (12)	0.0457 (12)	0.0018 (9)	0.0088 (8)	−0.0022 (9)
N3	0.0656 (14)	0.0708 (17)	0.0651 (15)	−0.0111 (13)	0.0067 (11)	0.0144 (14)
O1	0.0330 (8)	0.0832 (14)	0.0482 (10)	−0.0031 (8)	0.0087 (7)	0.0094 (9)
O2	0.0396 (10)	0.177 (3)	0.0465 (11)	0.0017 (12)	0.0101 (8)	0.0107 (13)
O3	0.0381 (9)	0.0839 (15)	0.0584 (12)	0.0009 (9)	0.0113 (8)	0.0078 (10)
O4	0.0494 (9)	0.0605 (12)	0.0436 (9)	0.0053 (8)	0.0091 (7)	0.0083 (8)

Geometric parameters (Å, º) top

C1—O1	1.363 (2)	C12—N2	1.401 (3)
C1—C2	1.377 (3)	C12—C13	1.415 (3)
C1—C6	1.393 (3)	C13—N3	1.141 (3)
C2—C3	1.384 (3)	C14—O3	1.210 (3)
C2—H2	0.9300	C14—O4	1.334 (3)
C3—C4	1.372 (3)	C15—O4	1.445 (3)
C3—H3	0.9300	C15—C16	1.486 (4)
C4—C5	1.378 (4)	C15—H15A	0.9700
C4—Cl1	1.742 (2)	C15—H15B	0.9700
C5—C6	1.367 (3)	C16—H16A	0.9600
C5—H5	0.9300	C16—H16B	0.9600
C6—Cl2	1.734 (3)	C16—H16C	0.9600
C7—O1	1.415 (2)	C17—C18	1.368 (4)
C7—C8	1.513 (3)	C17—C22	1.370 (3)
C7—H7A	0.9700	C17—N2	1.440 (3)
C7—H7B	0.9700	C18—C19	1.394 (3)
C8—O2	1.213 (3)	C18—H18	0.9300
C8—N1	1.335 (3)	C19—C20	1.365 (4)
C9—C12	1.381 (3)	C19—H19	0.9300
C9—N1	1.395 (3)	C20—C21	1.356 (4)
C9—C10	1.416 (3)	C20—H20	0.9300
C10—C11	1.371 (3)	C21—C22	1.384 (3)
C10—C14	1.458 (3)	C21—H21	0.9300
C11—N2	1.345 (3)	C22—H22	0.9300
C11—H11	0.9300	N1—H1	0.82 (2)

O1—C1—C2	124.7 (2)	O3—C14—C10	123.1 (2)
O1—C1—C6	116.3 (2)	O4—C14—C10	112.99 (19)
C2—C1—C6	119.0 (2)	O4—C15—C16	108.3 (2)
C1—C2—C3	120.7 (2)	O4—C15—H15A	110.0
C1—C2—H2	119.7	C16—C15—H15A	110.0
C3—C2—H2	119.7	O4—C15—H15B	110.0
C4—C3—C2	119.1 (2)	C16—C15—H15B	110.0
C4—C3—H3	120.5	H15A—C15—H15B	108.4
C2—C3—H3	120.5	C15—C16—H16A	109.5
C3—C4—C5	121.2 (2)	C15—C16—H16B	109.5
C3—C4—Cl1	119.2 (2)	H16A—C16—H16B	109.5
C5—C4—Cl1	119.60 (19)	C15—C16—H16C	109.5
C6—C5—C4	119.3 (2)	H16A—C16—H16C	109.5
C6—C5—H5	120.3	H16B—C16—H16C	109.5
C4—C5—H5	120.3	C18—C17—C22	120.9 (2)
C5—C6—C1	120.7 (2)	C18—C17—N2	120.8 (2)
C5—C6—Cl2	119.96 (19)	C22—C17—N2	118.3 (2)
C1—C6—Cl2	119.30 (18)	C17—C18—C19	118.9 (3)
O1—C7—C8	109.44 (19)	C17—C18—H18	120.5
O1—C7—H7A	109.8	C19—C18—H18	120.5
C8—C7—H7A	109.8	C20—C19—C18	119.9 (3)
O1—C7—H7B	109.8	C20—C19—H19	120.0
C8—C7—H7B	109.8	C18—C19—H19	120.0
H7A—C7—H7B	108.2	C21—C20—C19	120.7 (3)
O2—C8—N1	123.9 (2)	C21—C20—H20	119.6
O2—C8—C7	118.8 (2)	C19—C20—H20	119.6
N1—C8—C7	117.25 (19)	C20—C21—C22	120.1 (3)
C12—C9—N1	129.6 (2)	C20—C21—H21	119.9
C12—C9—C10	107.26 (19)	C22—C21—H21	119.9
N1—C9—C10	123.14 (18)	C17—C22—C21	119.4 (3)
C11—C10—C9	107.27 (19)	C17—C22—H22	120.3
C11—C10—C14	127.6 (2)	C21—C22—H22	120.3
C9—C10—C14	124.99 (19)	C8—N1—C9	125.75 (19)
N2—C11—C10	109.4 (2)	C8—N1—H1	123.4 (17)
N2—C11—H11	125.3	C9—N1—H1	110.5 (18)
C10—C11—H11	125.3	C11—N2—C12	108.81 (17)
C9—C12—N2	107.22 (19)	C11—N2—C17	125.1 (2)
C9—C12—C13	133.6 (2)	C12—N2—C17	125.30 (19)
N2—C12—C13	118.87 (18)	C1—O1—C7	116.70 (18)
N3—C13—C12	173.9 (2)	C14—O4—C15	116.29 (18)
O3—C14—O4	123.9 (2)

O1—C1—C2—C3	179.2 (2)	C22—C17—C18—C19	0.2 (4)
C6—C1—C2—C3	−0.7 (4)	N2—C17—C18—C19	179.4 (2)
C1—C2—C3—C4	0.2 (4)	C17—C18—C19—C20	−0.2 (5)
C2—C3—C4—C5	0.1 (4)	C18—C19—C20—C21	0.0 (5)
C2—C3—C4—Cl1	178.79 (19)	C19—C20—C21—C22	0.3 (5)
C3—C4—C5—C6	0.2 (4)	C18—C17—C22—C21	0.1 (4)
Cl1—C4—C5—C6	−178.57 (18)	N2—C17—C22—C21	−179.2 (3)
C4—C5—C6—C1	−0.6 (4)	C20—C21—C22—C17	−0.4 (5)
C4—C5—C6—Cl2	179.78 (19)	O2—C8—N1—C9	5.3 (4)
O1—C1—C6—C5	−179.0 (2)	C7—C8—N1—C9	−175.4 (2)
C2—C1—C6—C5	0.9 (4)	C12—C9—N1—C8	−21.0 (4)
O1—C1—C6—Cl2	0.6 (3)	C10—C9—N1—C8	158.0 (2)
C2—C1—C6—Cl2	−179.51 (19)	C10—C11—N2—C12	0.3 (3)
O1—C7—C8—O2	−164.7 (3)	C10—C11—N2—C17	170.5 (2)
O1—C7—C8—N1	15.9 (3)	C9—C12—N2—C11	0.7 (3)
C12—C9—C10—C11	1.5 (3)	C13—C12—N2—C11	−173.6 (2)
N1—C9—C10—C11	−177.7 (2)	C9—C12—N2—C17	−169.5 (2)
C12—C9—C10—C14	−174.7 (2)	C13—C12—N2—C17	16.2 (3)
N1—C9—C10—C14	6.1 (4)	C18—C17—N2—C11	126.0 (3)
C9—C10—C11—N2	−1.1 (3)	C22—C17—N2—C11	−54.7 (3)
C14—C10—C11—N2	174.9 (2)	C18—C17—N2—C12	−65.4 (3)
N1—C9—C12—N2	177.8 (2)	C22—C17—N2—C12	113.9 (3)
C10—C9—C12—N2	−1.3 (2)	C2—C1—O1—C7	6.4 (3)
N1—C9—C12—C13	−9.1 (4)	C6—C1—O1—C7	−173.7 (2)
C10—C9—C12—C13	171.7 (3)	C8—C7—O1—C1	172.4 (2)
C11—C10—C14—O3	−175.9 (2)	O3—C14—O4—C15	0.9 (4)
C9—C10—C14—O3	−0.5 (4)	C10—C14—O4—C15	−177.4 (2)
C11—C10—C14—O4	2.5 (4)	C16—C15—O4—C14	179.6 (2)
C9—C10—C14—O4	177.9 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O3	0.82 (2)	2.15 (3)	2.813 (3)	137 (2)
C7—H7A···O2ⁱ	0.97	2.57	3.341 (3)	137
C3—H3···N3ⁱ	0.93	2.61	3.312 (3)	133

Symmetry code: (i) −x+2, y, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₂₂H₁₇Cl₂N₃O₄
M_r	458.29
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	298
a, b, c (Å)	32.8846 (18), 7.6224 (4), 17.2834 (9)
γ (°)	89.773 (1)
V (Å³)	4332.2 (4)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.33
Crystal size (mm)	0.10 × 0.10 × 0.10

Data collection
Diffractometer	Bruker SMART 4K CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2003)
T_min, T_max	0.968, 0.968
No. of measured, independent and observed [I > 2σ(I)] reflections	16521, 4279, 3034
R_int	0.081
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.066, 0.154, 0.99
No. of reflections	4279
No. of parameters	285
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.32, −0.31

Computer programs: SMART (Bruker, 2001), SAINT-Plus (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O3	0.82 (2)	2.15 (3)	2.813 (3)	137 (2)
C7—H7A···O2ⁱ	0.97	2.57	3.341 (3)	136.7
C3—H3···N3ⁱ	0.93	2.61	3.312 (3)	132.5

Symmetry code: (i) −x+2, y, −z+1/2.

Acknowledgements

We gratefully acknowledge financial support of this work by the Key Science Research Project of Hubei Provincial Department of Education (No. D20092406) and the Science Research Project of Yunyang Medical College (No. 2007QDJ14).

References

Bruker (2001). SMART and SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
He, P., Peng, X.-M. & Li, G.-H. (2007a). Acta Cryst. E63, o4884. Web of Science CSD CrossRef IUCr Journals Google Scholar
He, P., Zheng, A., Cai, C.-Q. & Fang, C.-L. (2007b). Acta Cryst. E63, o3185. Web of Science CSD CrossRef IUCr Journals Google Scholar
Li, L. & Xu, S. (1995). Acta Pharm. Sin. 30, 556–560. CAS Google Scholar
Sheldrick, G. M. (2003). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Xue, S., Yan, L. & Fang, H. (2007). J. Shanghai Normal Univ. 36, 79–82. Google Scholar

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Volume 65| Part 8| August 2009| Page o1950

doi:10.1107/S1600536809027809

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

Ethyl 5-cyano-4-[2-(2,4-di­chloro­phen­­oxy)acetamido]-1-phenyl-1H-pyrrole-3-carboxyl­ate

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Experimental

Crystal data

Data collection

Refinement

Supporting information

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References

organic compounds

Ethyl 5-cyano-4-[2-(2,4-dichlorophenoxy)acetamido]-1-phenyl-1H-pyrrole-3-carboxylate