In the molecule of the title compound, C
22H
17ClN
2O
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, molecules are linked into dimers by intermolecular C—H

O hydrogen bonds.
Supporting information
CCDC reference: 709355
Key indicators
- Single-crystal X-ray study
- T = 296 K
- Mean
(C-C) = 0.004 Å
- R factor = 0.051
- wR factor = 0.142
- Data-to-parameter ratio = 13.6
checkCIF/PLATON results
No syntax errors found
Alert level C
Value of measurement temperature given = 296.000
Value of melting point given = 0.000
PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.17 Ratio
PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.64 Ratio
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C21
PLAT128_ALERT_4_C Non-standard setting of Space-group C2/c .... I2/a
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
4 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
2 ALERT type 2 Indicator that the structure model may be wrong or deficient
1 ALERT type 3 Indicator that the structure quality may be low
1 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
To a 0.1 M solution of ethyl 4-(2-chloroquinolin-3-yl)-1-phenylpyrrole
-3-carboxylate (1.5 mmol) in dry THF (15 ml) 2.5 equivalents of activated
MnO2 were added. The mixture was refluxed for 2.5 h. The same amount of
activated MnO2 was then added, and the reflux was continued for an
additional 2.5 h. After cooling, the mixture was diluted with THF, filtered
through Celite and washed with THF (5x5 ml). The filtrate was concentrated
under reduced pressure, diluted with CH2Cl2 and washed with water (2x5 ml).
The organic layers were separated and dried over anhydrous MgSO4. The
filtrate was concentrated and the residue was purified by flash chromatography
on silica gel using AcOEt/pentane (2:1 v/v) as eluent to afford the
corresponding pure pyrrole derivative.
Crystals suitable for X-ray analysis were
obtained by slow evaporation of the solvent.
All H atoms were introduced in calculated positions and treated as riding,
with C—H = 0.93-0.97 Å, and with Uiso(H) = 1.2
Ueq(C) or 1.5 Ueq(C) for methyl hydrogen atoms.
Data collection: COLLECT (Nonius, 1998); cell refinement: DENZO/SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO/SCALEPACK (Otwinowski & Minor, 1997); 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).
Ethyl 4-(2-chloroquinolin-3-yl)-1-phenyl-1
H-pyrrole-3-carboxylate
top
Crystal data top
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 | |
Data collection top
Nonius KappaCCD diffractometer | 2343 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.043 |
Graphite monochromator | 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 top
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 |
Crystal data top
C22H17ClN2O2 | V = 3768.6 (4) Å3 |
Mr = 376.83 | Z = 8 |
Monoclinic, I2/a | Mo Kα radiation |
a = 20.2021 (6) Å | µ = 0.22 mm−1 |
b = 8.0500 (1) Å | T = 296 K |
c = 24.0238 (7) Å | 0.15 × 0.06 × 0.05 mm |
β = 105.29 (2)° | |
Data collection top
Nonius KappaCCD diffractometer | 2343 reflections with I > 2σ(I) |
9812 measured reflections | Rint = 0.043 |
3315 independent reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.051 | 0 restraints |
wR(F2) = 0.142 | H-atom parameters constrained |
S = 1.02 | Δρmax = 0.29 e Å−3 |
3315 reflections | Δρmin = −0.27 e Å−3 |
244 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 | 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* | |
Atomic displacement parameters (Å2) top | 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) |
Geometric parameters (Å, º) top
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) |
Hydrogen-bond geometry (Å, º) top
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) −x+1/2, −y−1/2, −z+1/2. |
Experimental details
Crystal data |
Chemical formula | C22H17ClN2O2 |
Mr | 376.83 |
Crystal system, space group | Monoclinic, I2/a |
Temperature (K) | 296 |
a, b, c (Å) | 20.2021 (6), 8.0500 (1), 24.0238 (7) |
β (°) | 105.29 (2) |
V (Å3) | 3768.6 (4) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.22 |
Crystal size (mm) | 0.15 × 0.06 × 0.05 |
|
Data collection |
Diffractometer | Nonius KappaCCD diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 9812, 3315, 2343 |
Rint | 0.043 |
(sin θ/λ)max (Å−1) | 0.596 |
|
Refinement |
R[F2 > 2σ(F2)], wR(F2), S | 0.051, 0.142, 1.02 |
No. of reflections | 3315 |
No. of parameters | 244 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.29, −0.27 |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C12—H12···O1i | 0.9300 | 2.5000 | 3.383 (3) | 159.00 |
C15—H15···O1i | 0.9300 | 2.4500 | 3.275 (4) | 148.00 |
Symmetry code: (i) −x+1/2, −y−1/2, −z+1/2. |
Heterocyclic compounds and particularly five and six membered ring compounds occupy a prominent place among various classes of organic compounds for their diverse biological activities. Among a wide variety of heterocycles that have been explored for developing pharmaceutically important molecules (Raj Amal et al., 2003), quinolines have played an important role in medicine chemistry (Wright et al., 2001; Sahu et al., 2002). Some of them have received considerable attention due to their presence in numerous natural products along with their wide ranging application as drugs, pharmaceutical and agrochemicals (Michael, 1997). Pyrroles are an important class of heterocyclic compounds and are widely used in synthetic organic chemistry and material science (Corvo & Pereira, 2002; Harrison et al., 2006). Pyrroles are often seen as building blocks in naturally occurring and biologically active compounds such as heme, chlorophyll and vitamin B12 (Demir et al., 2005; Bigg & Bonnaud, 1994; Tsukamoto et al., 2001). Syntheses of pyrroloquinolines derivatives were not particularly numerous in the literature before the initial report of the unique alkaloids (Witherup et al., 1995). In a continuation of our program on the synthesis and biological evaluation of quinolines derivatives (Belfaitah et al., 2006; Bouraiou et al., 2008; Rezig et al., 2000; Moussaoui et al., 2002), we have elaborated an efficient route for the synthesis of 3-pyrrolylquinolines by dehydrogenation of 3-pyrrolidinyl quinolines using activated manganese dioxide in refluxing THF during 5 h (Menasra et al., 2005; Benzerka et al. 2008). We report here the crystal structure of a new N-phenylpyrrole derivative bearing a quinoline ring at C-3 and an ester group at C-4.
The molecular structure and the atom-numbering scheme of the title compound are shown in Fig. 1. The quinoline ring system is essentially planar, the dihedral angle formed by the six-membered rings being only 0.64 (8)°. The dihedral angles between the pyrrole ring and the quinoline and phenyl rings are 67.93 (8) and 28.40 (11)°, respectively. The geometric parameters are in agreement with those of other structures possessing a quinolyl substituent previously reported in the literature (Belfaitah et al., 2006; Bouraiou et al., 2008). In the crystal structure (Fig. 2), molecules are linked into dimers by intermolecular C—H···O hydrogen bonds (Table 1).