Ethyl 4-(2-chloro-quinolin-3-yl)-1-phenyl-1H-pyrrole-3-carboxyl-ate.

In the mol-ecule of the title compound, C(22)H(17)ClN(2)O(2), the dihedral angles formed by the pyrrole ring with the quinoline and phenyl rings are 67.93 (8) and 28.40 (11)°, respectively. In the crystal structure, mol-ecules are linked into dimers by inter-molecular C-H⋯O hydrogen bonds.

Related literature

For general background, see: Corvo & Pereira (2002 ▶); Harrison et al. (2006 ▶); Wright et al. (2001 ▶); Sahu et al. (2002 ▶); Michael (1997 ▶); Rezig et al. (2000 ▶); Raj Amal et al. (2003 ▶); Witherup et al. (1995 ▶); Moussaoui et al. (2002 ▶). For related structures, see: Belfaitah et al. (2006 ▶); Bouraiou et al. (2008 ▶);. For details of the synthesis, see: Menasra et al. (2005 ▶); Benzerka et al. (2008 ▶). For pyrroles as building blocks in naturally occurring and biologically active compounds such as heme, chloro­phyll and vitamin B12, see: Bigg & Bonnaud (1994 ▶); Demir et al. (2005 ▶); Tsukamoto et al. (2001 ▶);

Experimental

Crystal data

C22H17ClN2O2

M = 376.83

Monoclinic,

a = 20.2021 (6) Å

b = 8.0500 (1) Å

c = 24.0238 (7) Å

β = 105.29 (2)°

V = 3768.6 (4) Å3

Z = 8

Mo Kα radiation

μ = 0.22 mm−1

T = 296 (2) K

0.15 × 0.06 × 0.05 mm

Data collection

Nonius KappaCCD diffractometer

Absorption correction: none

9812 measured reflections

3315 independent reflections

2343 reflections with I > 2σ(I)

R int = 0.043

Refinement

R[F 2 > 2σ(F 2)] = 0.051

wR(F 2) = 0.142

S = 1.02

3315 reflections

244 parameters

H-atom parameters constrained

Δρmax = 0.29 e Å−3

Δρmin = −0.27 e Å−3

Data collection: COLLECT (Nonius, 1998 ▶); cell refinement: DENZO/SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: DENZO/SCALEPACK; program(s) used to solve structure: SIR2002 (Burla et al., 2003 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and DIAMOND (Brandenburg & Berndt, 2001 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808032546/rz2251sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808032546/rz2251Isup2.hkl

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

C22H17ClN2O2	F(000) = 1568
Mr = 376.83	Dx = 1.328 Mg m−3
Monoclinic, I2/a	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -I 2ya	Cell parameters from 9812 reflections
a = 20.2021 (6) Å	θ = 5.1–25.1°
b = 8.0500 (1) Å	µ = 0.22 mm−1
c = 24.0238 (7) Å	T = 296 K
β = 105.29 (2)°	Needle, white
V = 3768.6 (4) Å3	0.15 × 0.06 × 0.05 mm
Z = 8

Nonius KappaCCD diffractometer	2343 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.043
graphite	θmax = 25.1°, θmin = 5.1°
φ scans, and ω scans with κ offsets	h = −23→24
9812 measured reflections	k = −9→9
3315 independent reflections	l = −28→28

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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.142	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.103P)2 + 0.3358P] where P = (Fo2 + 2Fc2)/3
3315 reflections	(Δ/σ)max < 0.001
244 parameters	Δρmax = 0.29 e Å−3
0 restraints	Δρmin = −0.27 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
Cl1	0.12476 (3)	0.20796 (10)	0.35827 (3)	0.0669 (3)
O1	0.19940 (10)	−0.3023 (3)	0.31308 (8)	0.0722 (6)
C13	0.12321 (12)	−0.1022 (3)	0.25970 (10)	0.0454 (6)
N2	0.10945 (10)	0.0124 (3)	0.17336 (8)	0.0480 (5)
N1	0.00661 (12)	0.1516 (3)	0.37746 (9)	0.0607 (6)
C3	−0.04742 (13)	−0.0147 (3)	0.27328 (11)	0.0515 (6)
H3	−0.0658	−0.0671	0.2381	0.062*
O2	0.11506 (10)	−0.2065 (3)	0.34790 (8)	0.0696 (6)
C20	0.15071 (12)	−0.2127 (3)	0.30819 (10)	0.0489 (6)
C12	0.14907 (12)	−0.0931 (3)	0.21243 (10)	0.0483 (6)
H12	0.1874	−0.1498	0.2079	0.058*
C1	0.04143 (13)	0.1247 (3)	0.34028 (10)	0.0509 (6)
C14	0.12066 (13)	0.0599 (3)	0.11921 (10)	0.0507 (6)
C10	0.06434 (12)	0.0057 (3)	0.24895 (10)	0.0445 (5)
C11	0.05718 (12)	0.0714 (3)	0.19565 (10)	0.0490 (6)
H11	0.0227	0.1444	0.1770	0.059*
C2	0.01905 (12)	0.0392 (3)	0.28691 (10)	0.0455 (6)
C4	−0.08852 (13)	0.0083 (3)	0.31192 (12)	0.0555 (7)
C9	−0.05921 (14)	0.0900 (4)	0.36430 (12)	0.0601 (7)
C5	−0.15703 (14)	−0.0503 (4)	0.30059 (15)	0.0705 (8)
H5	−0.1772	−0.1042	0.2660	0.085*
C16	0.19620 (18)	0.1089 (5)	0.05969 (13)	0.0772 (9)
H16	0.2402	0.1075	0.0546	0.093*
C15	0.18577 (15)	0.0595 (4)	0.11161 (12)	0.0635 (7)
H15	0.2228	0.0258	0.1415	0.076*
C7	−0.1635 (2)	0.0529 (5)	0.39232 (18)	0.0898 (11)
H7	−0.1889	0.0675	0.4190	0.108*
C6	−0.19327 (17)	−0.0274 (4)	0.34045 (18)	0.0827 (10)
H6	−0.2382	−0.0658	0.3330	0.099*
C8	−0.09838 (17)	0.1100 (5)	0.40466 (15)	0.0802 (10)
H8	−0.0793	0.1626	0.4397	0.096*
C19	0.06632 (17)	0.1077 (5)	0.07449 (12)	0.0823 (10)
H19	0.0219	0.1053	0.0788	0.099*
C17	0.14196 (19)	0.1601 (5)	0.01550 (13)	0.0817 (10)
H17	0.1492	0.1950	−0.0193	0.098*
C21	0.1396 (2)	−0.3041 (5)	0.39981 (13)	0.0838 (10)
H21A	0.1874	−0.3336	0.4046	0.101*
H21B	0.1132	−0.4057	0.3970	0.101*
C18	0.07782 (19)	0.1593 (6)	0.02294 (13)	0.0936 (12)
H18	0.0410	0.1940	−0.0070	0.112*
C22	0.1328 (3)	−0.2075 (6)	0.44902 (17)	0.141 (2)
H22A	0.1489	−0.2719	0.4836	0.211*
H22B	0.0855	−0.1791	0.4441	0.211*
H22C	0.1596	−0.1078	0.4519	0.211*

	U11	U22	U33	U12	U13	U23
Cl1	0.0655 (4)	0.0788 (5)	0.0550 (4)	−0.0096 (4)	0.0136 (3)	−0.0156 (3)
O1	0.0693 (12)	0.0869 (15)	0.0660 (12)	0.0322 (12)	0.0276 (10)	0.0229 (11)
C13	0.0496 (12)	0.0459 (14)	0.0408 (12)	0.0020 (11)	0.0120 (10)	−0.0005 (10)
N2	0.0535 (11)	0.0519 (12)	0.0399 (10)	0.0034 (10)	0.0144 (9)	0.0006 (9)
N1	0.0674 (14)	0.0676 (15)	0.0516 (12)	0.0092 (12)	0.0239 (11)	−0.0019 (11)
C3	0.0547 (14)	0.0473 (15)	0.0517 (14)	0.0051 (11)	0.0127 (11)	0.0025 (11)
O2	0.0821 (13)	0.0810 (14)	0.0542 (11)	0.0318 (11)	0.0330 (10)	0.0230 (10)
C20	0.0540 (14)	0.0486 (14)	0.0461 (13)	0.0043 (12)	0.0170 (11)	0.0016 (11)
C12	0.0521 (13)	0.0487 (15)	0.0456 (13)	0.0050 (11)	0.0154 (11)	0.0002 (11)
C1	0.0578 (14)	0.0514 (15)	0.0443 (13)	0.0036 (12)	0.0153 (11)	−0.0017 (11)
C14	0.0635 (15)	0.0514 (15)	0.0379 (12)	0.0035 (12)	0.0143 (11)	0.0013 (11)
C10	0.0483 (12)	0.0434 (13)	0.0413 (12)	0.0015 (11)	0.0112 (10)	−0.0039 (10)
C11	0.0502 (13)	0.0497 (14)	0.0466 (13)	0.0060 (11)	0.0116 (10)	−0.0004 (11)
C2	0.0512 (13)	0.0424 (14)	0.0428 (13)	0.0056 (10)	0.0124 (10)	0.0010 (10)
C4	0.0578 (15)	0.0498 (15)	0.0622 (16)	0.0104 (12)	0.0219 (12)	0.0127 (13)
C9	0.0659 (16)	0.0611 (18)	0.0589 (16)	0.0149 (14)	0.0262 (13)	0.0082 (13)
C5	0.0592 (16)	0.0652 (19)	0.091 (2)	0.0067 (14)	0.0263 (16)	0.0113 (16)
C16	0.088 (2)	0.093 (2)	0.0613 (18)	0.0162 (19)	0.0381 (16)	0.0154 (17)
C15	0.0694 (17)	0.0738 (19)	0.0515 (15)	0.0134 (15)	0.0235 (13)	0.0112 (14)
C7	0.089 (2)	0.103 (3)	0.095 (3)	0.020 (2)	0.054 (2)	0.016 (2)
C6	0.0617 (17)	0.078 (2)	0.117 (3)	0.0093 (17)	0.0390 (19)	0.025 (2)
C8	0.083 (2)	0.094 (3)	0.078 (2)	0.0131 (19)	0.0467 (18)	0.0042 (18)
C19	0.0695 (18)	0.125 (3)	0.0500 (16)	0.014 (2)	0.0121 (14)	0.0124 (18)
C17	0.110 (3)	0.094 (3)	0.0478 (16)	0.016 (2)	0.0330 (17)	0.0147 (16)
C21	0.113 (3)	0.089 (2)	0.0569 (18)	0.034 (2)	0.0361 (17)	0.0305 (17)
C18	0.092 (2)	0.138 (4)	0.0473 (17)	0.025 (2)	0.0121 (16)	0.0218 (19)
C22	0.245 (6)	0.113 (4)	0.061 (2)	0.023 (4)	0.035 (3)	0.017 (2)

Cl1—C1	1.757 (3)	C9—C8	1.413 (4)
O1—C20	1.200 (3)	C5—C6	1.362 (4)
C13—C12	1.371 (3)	C5—H5	0.9300
C13—C10	1.440 (3)	C16—C17	1.373 (5)
C13—C20	1.454 (3)	C16—C15	1.377 (4)
N2—C12	1.359 (3)	C16—H16	0.9300
N2—C11	1.388 (3)	C15—H15	0.9300
N2—C14	1.430 (3)	C7—C8	1.350 (5)
N1—C1	1.293 (3)	C7—C6	1.392 (5)
N1—C9	1.376 (4)	C7—H7	0.9300
C3—C2	1.366 (3)	C6—H6	0.9300
C3—C4	1.411 (3)	C8—H8	0.9300
C3—H3	0.9300	C19—C18	1.383 (4)
O2—C20	1.339 (3)	C19—H19	0.9300
O2—C21	1.446 (3)	C17—C18	1.354 (5)
C12—H12	0.9300	C17—H17	0.9300
C1—C2	1.420 (3)	C21—C22	1.451 (5)
C14—C19	1.373 (4)	C21—H21A	0.9700
C14—C15	1.375 (4)	C21—H21B	0.9700
C10—C11	1.357 (3)	C18—H18	0.9300
C10—C2	1.477 (3)	C22—H22A	0.9600
C11—H11	0.9300	C22—H22B	0.9600
C4—C9	1.405 (4)	C22—H22C	0.9600
C4—C5	1.419 (4)
C12—C13—C10	107.2 (2)	C6—C5—H5	120.1
C12—C13—C20	123.2 (2)	C4—C5—H5	120.1
C10—C13—C20	129.5 (2)	C17—C16—C15	120.4 (3)
C12—N2—C11	108.49 (19)	C17—C16—H16	119.8
C12—N2—C14	126.1 (2)	C15—C16—H16	119.8
C11—N2—C14	125.3 (2)	C14—C15—C16	120.0 (3)
C1—N1—C9	116.8 (2)	C14—C15—H15	120.0
C2—C3—C4	120.8 (2)	C16—C15—H15	120.0
C2—C3—H3	119.6	C8—C7—C6	121.4 (3)
C4—C3—H3	119.6	C8—C7—H7	119.3
C20—O2—C21	117.9 (2)	C6—C7—H7	119.3
O1—C20—O2	122.2 (2)	C5—C6—C7	120.4 (3)
O1—C20—C13	125.2 (2)	C5—C6—H6	119.8
O2—C20—C13	112.6 (2)	C7—C6—H6	119.8
N2—C12—C13	108.8 (2)	C7—C8—C9	120.0 (4)
N2—C12—H12	125.6	C7—C8—H8	120.0
C13—C12—H12	125.6	C9—C8—H8	120.0
N1—C1—C2	127.1 (2)	C14—C19—C18	119.8 (3)
N1—C1—Cl1	115.3 (2)	C14—C19—H19	120.1
C2—C1—Cl1	117.60 (18)	C18—C19—H19	120.1
C19—C14—C15	119.5 (2)	C18—C17—C16	119.5 (3)
C19—C14—N2	120.1 (2)	C18—C17—H17	120.2
C15—C14—N2	120.4 (2)	C16—C17—H17	120.2
C11—C10—C13	106.4 (2)	O2—C21—C22	109.1 (3)
C11—C10—C2	125.6 (2)	O2—C21—H21A	109.9
C13—C10—C2	128.0 (2)	C22—C21—H21A	109.9
C10—C11—N2	109.1 (2)	O2—C21—H21B	109.9
C10—C11—H11	125.4	C22—C21—H21B	109.9
N2—C11—H11	125.4	H21A—C21—H21B	108.3
C3—C2—C1	115.4 (2)	C17—C18—C19	120.8 (3)
C3—C2—C10	121.6 (2)	C17—C18—H18	119.6
C1—C2—C10	123.0 (2)	C19—C18—H18	119.6
C9—C4—C3	117.9 (2)	C21—C22—H22A	109.5
C9—C4—C5	119.1 (3)	C21—C22—H22B	109.5
C3—C4—C5	122.9 (3)	H22A—C22—H22B	109.5
N1—C9—C4	121.9 (2)	C21—C22—H22C	109.5
N1—C9—C8	118.9 (3)	H22A—C22—H22C	109.5
C4—C9—C8	119.2 (3)	H22B—C22—H22C	109.5
C6—C5—C4	119.9 (3)
C21—O2—C20—O1	4.1 (4)	Cl1—C1—C2—C10	5.3 (3)
C21—O2—C20—C13	−176.6 (3)	C11—C10—C2—C3	67.9 (4)
C12—C13—C20—O1	2.5 (4)	C13—C10—C2—C3	−111.1 (3)
C10—C13—C20—O1	178.0 (3)	C11—C10—C2—C1	−113.8 (3)
C12—C13—C20—O2	−176.7 (2)	C13—C10—C2—C1	67.2 (4)
C10—C13—C20—O2	−1.3 (4)	C2—C3—C4—C9	0.8 (4)
C11—N2—C12—C13	−0.3 (3)	C2—C3—C4—C5	−177.9 (3)
C14—N2—C12—C13	177.7 (2)	C1—N1—C9—C4	−2.8 (4)
C10—C13—C12—N2	−0.5 (3)	C1—N1—C9—C8	177.4 (3)
C20—C13—C12—N2	175.8 (2)	C3—C4—C9—N1	2.2 (4)
C9—N1—C1—C2	0.4 (4)	C5—C4—C9—N1	−179.1 (3)
C9—N1—C1—Cl1	179.1 (2)	C3—C4—C9—C8	−178.0 (3)
C12—N2—C14—C19	153.2 (3)	C5—C4—C9—C8	0.7 (4)
C11—N2—C14—C19	−29.2 (4)	C9—C4—C5—C6	−0.3 (4)
C12—N2—C14—C15	−27.3 (4)	C3—C4—C5—C6	178.4 (3)
C11—N2—C14—C15	150.3 (3)	C19—C14—C15—C16	0.9 (5)
C12—C13—C10—C11	1.1 (3)	N2—C14—C15—C16	−178.6 (3)
C20—C13—C10—C11	−174.9 (2)	C17—C16—C15—C14	0.5 (5)
C12—C13—C10—C2	−179.8 (2)	C4—C5—C6—C7	−0.1 (5)
C20—C13—C10—C2	4.2 (4)	C8—C7—C6—C5	0.0 (6)
C13—C10—C11—N2	−1.2 (3)	C6—C7—C8—C9	0.5 (6)
C2—C10—C11—N2	179.6 (2)	N1—C9—C8—C7	179.0 (3)
C12—N2—C11—C10	1.0 (3)	C4—C9—C8—C7	−0.9 (5)
C14—N2—C11—C10	−177.0 (2)	C15—C14—C19—C18	−1.9 (5)
C4—C3—C2—C1	−2.9 (4)	N2—C14—C19—C18	177.6 (3)
C4—C3—C2—C10	175.5 (2)	C15—C16—C17—C18	−1.0 (6)
N1—C1—C2—C3	2.4 (4)	C20—O2—C21—C22	139.1 (4)
Cl1—C1—C2—C3	−176.30 (19)	C16—C17—C18—C19	0.0 (6)
N1—C1—C2—C10	−176.0 (3)	C14—C19—C18—C17	1.5 (6)

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12···O1i	0.93	2.50	3.383 (3)	159
C15—H15···O1i	0.93	2.45	3.275 (4)	148

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C12—H12⋯O1i	0.93	2.50	3.383 (3)	159
C15—H15⋯O1i	0.93	2.45	3.275 (4)	148

Symmetry code: (i) .