organic compounds
1-[6-Chloro-2-(phenanthren-9-yl)quinolin-4-yl]pyrrolidin-2-one
aDepartment of Physics, Presidency College (Autonomous), Chennai 600 005, India, and bOrganic Chemistry Division, CSIR Central Leather Research Institute, Chennai 600 020, India
*Correspondence e-mail: dhanapal.ramu@gmail.com
In the title compound, C27H19ClN2O, the quinoline system is planar, with a maximum deviation from the mean plane of 0.003 Å for the N atom. This ring makes dihedral angles of 56.64 (5) and 49.26 (2)° with phenanthrene and pyrrolidine rings, respectively. The pyrrolidine ring adopts a twisted conformation. In the crystal, molecules are linked via C—H⋯O hydrogen bonds, forming a two-dimensional network lying parallel to (010).
Keywords: crystal structure; quinoline; pyrrolidine; phenanthrene.
CCDC reference: 1471078
Structure description
A large number of natural products contain the quinoline and pyrrolidine heterocycles, and they are found in numerous commercial products, including pharmaceuticals, fragrances and dyes (Padwa et al., 1999). Pyrrolidine derivatives are found to have anticonvulsant, antimicrobial and antifungal activities against various pathogens (Amal Raj et al., 2003).
In the molecular structure of the title molecule (Fig. 1), the chlorobenzene ring belonging to the quinoline system adopts an almost planar conformation with a maximum deviation of 0.162 Å for Cl1. The pyrrolidine ring N1/C18–C21 adopts a twisted conformation with puckering parameters q2 = 0.112 (3) Å and φ = 25.4 (15)°. This latter ring forms dihedral angles of 49.26 (2) and 49.27 (8)° with the quinoline and phenanthrene rings, respectively. The keto atom O1 in the 2-pyrrolidinone group deviates by 0.128 Å from the pyrrolidine mean plane.
In the via C—H⋯O intermolecular hydrogen bonds, forming a two-dimensional network lying parallel to the (010) plane (Table 1 and Fig. 2).
molecules are linkedSynthesis and crystallization
4-Chloroaniline (2.4 mmol), which was reacted with pyrene-1-carboxaldehyde (2.4 mmol) and N-vinyl-2-pyrrolidinone (2.5 mmol) in the presence of scandium(III) trifluoromethanesulfonate (5 mol %), in acetonitrile. This reaction was carried out at 80°C, and after completion, the reaction mixture was filtered and washed with acetonitrile. The overall yield was 85%. The product was dissolved in chloroform and heated for two minutes. The resulting solution was subjected to crystallization by slow evaporation of the solvent over two days, resulting in the formation of single crystals.
Refinement
Crystal data, data collection and structure .
details are summarized in Table 2Structural data
CCDC reference: 1471078
10.1107/S2414314616005290/bh4004sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S2414314616005290/bh4004Isup2.hkl
Supporting information file. DOI: 10.1107/S2414314616005290/bh4004Isup3.cml
4-Chloroaniline (2.4 mmol), which was reacted with pyrene-1-carboxaldehyde (2.4 mmol) and N-vinyl-2-pyrrolidinone (2.5 mmol) in the presence of scandium(III) trifluoromethanesulfonate (5 mol %), in acetonitrile. This reaction was carried out at 80°C, and after completion, the reaction mixture was filtered and washed with acetonitrile. The overall yield was 85%. The product was dissolved in chloroform and heated for two minutes. The resulting solution was subjected to crystallization by slow evaporation of the solvent over two days, resulting in the formation of single crystals.
Crystal data, data collection and structure
details are summarized in Table 2. The was determined by of the (Flack, 1983), which converged to x = 0.11 (7).A large number of natural products contain the quinoline and pyrrolidine heterocycles, and they are found in numerous commercial products, including pharmaceuticals, fragrances and dyes (Padwa et al., 1999). Pyrrolidine derivatives are found to have anticonvulsant, antimicrobial and antifungal activities against various pathogens (Amal Raj et al., 2003).
In the molecular structure of the title molecule (Fig. 1), the chlorobenzene ring belonging to the quinoline system adopts an almost planar conformation with a maximum deviation of 0.162 Å for Cl1. The pyrrolidine ring N1/C18–C21 adopts a twisted conformation with puckering parameters q2 = 0.112 (3) Å and φ = 25.4 (15)°. This latter ring forms dihedral angles of 49.26 (2) and 49.27 (8)° with the quinoline and phenanthrene rings, respectively. The keto atom O1 in the 2-pyrrolidinone group deviates by 0.128 Å from the pyrrolidine mean plane.
In the
molecules are linked via C—H···O intermolecular hydrogen bonds, forming a two-dimensional network lying parallel to the (010) plane (Table 1 and Fig. 2).Data collection: APEX2 (Bruker, 2008); cell
SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009).Fig. 1. The molecular structure of the title compound, with displacement ellipsoids drawn at the 30% probability level. H atoms are shown as spheres of arbitrary radius. | |
Fig. 2. The molecular packing viewed down the b axis. |
C27H19ClN2O | F(000) = 880 |
Mr = 422.89 | Dx = 1.350 Mg m−3 |
Orthorhombic, Pna21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2c -2n | Cell parameters from 2845 reflections |
a = 14.824 (3) Å | θ = 2.4–25.0° |
b = 8.2946 (17) Å | µ = 0.21 mm−1 |
c = 16.924 (3) Å | T = 293 K |
V = 2081.0 (7) Å3 | Block, colourless |
Z = 4 | 0.25 × 0.20 × 0.20 mm |
Bruker SMART APEXII CCD diffractometer | 3530 independent reflections |
Radiation source: fine-focus sealed tube | 2845 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.027 |
ω and φ scans | θmax = 25.0°, θmin = 2.4° |
Absorption correction: multi-scan (SADABS; Bruker, 2008) | h = −17→13 |
Tmin = 0.952, Tmax = 0.960 | k = −9→9 |
8128 measured reflections | l = −20→19 |
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)] = 0.034 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.093 | w = 1/[σ2(Fo2) + (0.0494P)2 + 0.0804P] where P = (Fo2 + 2Fc2)/3 |
S = 1.06 | (Δ/σ)max < 0.001 |
3530 reflections | Δρmax = 0.15 e Å−3 |
280 parameters | Δρmin = −0.16 e Å−3 |
1 restraint | Absolute structure: Flack (1983) |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.11 (7) |
C27H19ClN2O | V = 2081.0 (7) Å3 |
Mr = 422.89 | Z = 4 |
Orthorhombic, Pna21 | Mo Kα radiation |
a = 14.824 (3) Å | µ = 0.21 mm−1 |
b = 8.2946 (17) Å | T = 293 K |
c = 16.924 (3) Å | 0.25 × 0.20 × 0.20 mm |
Bruker SMART APEXII CCD diffractometer | 3530 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2008) | 2845 reflections with I > 2σ(I) |
Tmin = 0.952, Tmax = 0.960 | Rint = 0.027 |
8128 measured reflections |
R[F2 > 2σ(F2)] = 0.034 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.093 | Δρmax = 0.15 e Å−3 |
S = 1.06 | Δρmin = −0.16 e Å−3 |
3530 reflections | Absolute structure: Flack (1983) |
280 parameters | Absolute structure parameter: 0.11 (7) |
1 restraint |
x | y | z | Uiso*/Ueq | ||
C1 | −0.05298 (16) | 0.8783 (3) | 0.71094 (14) | 0.0444 (6) | |
C2 | 0.01627 (17) | 0.7975 (3) | 0.75181 (15) | 0.0508 (6) | |
H2 | 0.0666 | 0.7618 | 0.7240 | 0.061* | |
C3 | 0.01143 (19) | 0.7702 (3) | 0.83100 (16) | 0.0596 (7) | |
H3 | 0.0578 | 0.7158 | 0.8567 | 0.072* | |
C4 | −0.0630 (2) | 0.8239 (4) | 0.87318 (17) | 0.0669 (8) | |
H4 | −0.0653 | 0.8093 | 0.9276 | 0.080* | |
C5 | −0.13266 (19) | 0.8978 (3) | 0.83552 (17) | 0.0602 (7) | |
H5 | −0.1828 | 0.9302 | 0.8645 | 0.072* | |
C6 | −0.13060 (16) | 0.9263 (3) | 0.75391 (15) | 0.0458 (6) | |
C7 | −0.20672 (17) | 0.9978 (3) | 0.71181 (16) | 0.0491 (6) | |
C8 | −0.28684 (19) | 1.0456 (4) | 0.7507 (2) | 0.0648 (8) | |
H8 | −0.2921 | 1.0320 | 0.8050 | 0.078* | |
C9 | −0.35642 (19) | 1.1118 (4) | 0.7090 (2) | 0.0755 (9) | |
H9 | −0.4086 | 1.1427 | 0.7354 | 0.091* | |
C10 | −0.35063 (19) | 1.1336 (4) | 0.6281 (2) | 0.0734 (9) | |
H10 | −0.3985 | 1.1796 | 0.6006 | 0.088* | |
C11 | −0.27442 (19) | 1.0874 (3) | 0.58848 (19) | 0.0621 (7) | |
H11 | −0.2708 | 1.1013 | 0.5340 | 0.075* | |
C12 | −0.20145 (16) | 1.0189 (3) | 0.62972 (17) | 0.0486 (6) | |
C13 | −0.12090 (17) | 0.9717 (3) | 0.58905 (15) | 0.0488 (6) | |
H13 | −0.1178 | 0.9863 | 0.5346 | 0.059* | |
C14 | −0.04928 (15) | 0.9070 (3) | 0.62676 (14) | 0.0433 (6) | |
C15 | 0.03207 (16) | 0.8673 (3) | 0.57893 (13) | 0.0422 (5) | |
C16 | 0.11754 (16) | 0.9326 (3) | 0.59887 (14) | 0.0441 (6) | |
H16 | 0.1234 | 0.9978 | 0.6432 | 0.053* | |
C17 | 0.19117 (15) | 0.8999 (3) | 0.55315 (13) | 0.0400 (5) | |
C18 | 0.30624 (17) | 0.9863 (4) | 0.65352 (15) | 0.0564 (7) | |
H18A | 0.3068 | 0.8833 | 0.6807 | 0.068* | |
H18B | 0.2668 | 1.0596 | 0.6818 | 0.068* | |
C19 | 0.4006 (2) | 1.0547 (4) | 0.64752 (17) | 0.0673 (8) | |
H19A | 0.4068 | 1.1487 | 0.6812 | 0.081* | |
H19B | 0.4448 | 0.9749 | 0.6636 | 0.081* | |
C20 | 0.41419 (16) | 1.1001 (3) | 0.56260 (15) | 0.0556 (7) | |
H20A | 0.4212 | 1.2159 | 0.5574 | 0.067* | |
H20B | 0.4676 | 1.0480 | 0.5415 | 0.067* | |
C21 | 0.33183 (15) | 1.0443 (3) | 0.51965 (16) | 0.0468 (6) | |
C22 | 0.18137 (15) | 0.7916 (3) | 0.48919 (13) | 0.0408 (5) | |
C23 | 0.25435 (16) | 0.7291 (3) | 0.44529 (14) | 0.0458 (6) | |
H23 | 0.3130 | 0.7622 | 0.4560 | 0.055* | |
C24 | 0.23791 (19) | 0.6196 (3) | 0.38689 (15) | 0.0535 (7) | |
C25 | 0.1507 (2) | 0.5708 (3) | 0.36694 (15) | 0.0614 (8) | |
H25 | 0.1415 | 0.4997 | 0.3252 | 0.074* | |
C26 | 0.07948 (19) | 0.6280 (3) | 0.40885 (15) | 0.0584 (7) | |
H26 | 0.0213 | 0.5955 | 0.3958 | 0.070* | |
C27 | 0.09297 (16) | 0.7365 (3) | 0.47227 (13) | 0.0435 (6) | |
Cl1 | 0.32930 (6) | 0.53261 (10) | 0.33873 (5) | 0.0793 (3) | |
N1 | 0.27677 (13) | 0.9669 (2) | 0.57219 (11) | 0.0426 (5) | |
N2 | 0.01915 (14) | 0.7756 (2) | 0.51683 (12) | 0.0472 (5) | |
O1 | 0.31649 (13) | 1.0648 (3) | 0.45001 (12) | 0.0693 (6) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0415 (13) | 0.0449 (12) | 0.0469 (14) | −0.0090 (11) | 0.0008 (12) | −0.0090 (11) |
C2 | 0.0424 (14) | 0.0554 (14) | 0.0545 (17) | −0.0058 (11) | −0.0011 (12) | −0.0031 (13) |
C3 | 0.0571 (16) | 0.0645 (16) | 0.0574 (18) | −0.0103 (13) | −0.0070 (15) | 0.0063 (14) |
C4 | 0.073 (2) | 0.081 (2) | 0.0466 (16) | −0.0090 (17) | 0.0010 (15) | 0.0048 (15) |
C5 | 0.0574 (16) | 0.0721 (17) | 0.0512 (16) | −0.0089 (14) | 0.0143 (15) | −0.0093 (15) |
C6 | 0.0419 (14) | 0.0497 (13) | 0.0457 (14) | −0.0072 (11) | 0.0045 (12) | −0.0101 (11) |
C7 | 0.0423 (15) | 0.0498 (14) | 0.0551 (16) | −0.0099 (11) | 0.0040 (12) | −0.0169 (11) |
C8 | 0.0445 (16) | 0.0788 (19) | 0.0711 (19) | −0.0060 (15) | 0.0093 (15) | −0.0211 (16) |
C9 | 0.0409 (16) | 0.084 (2) | 0.101 (3) | 0.0031 (15) | 0.0036 (18) | −0.0272 (19) |
C10 | 0.0451 (17) | 0.0728 (18) | 0.102 (3) | 0.0040 (14) | −0.0187 (18) | −0.0194 (18) |
C11 | 0.0505 (16) | 0.0644 (16) | 0.0714 (19) | −0.0024 (14) | −0.0104 (15) | −0.0170 (15) |
C12 | 0.0405 (14) | 0.0461 (13) | 0.0591 (18) | −0.0027 (11) | −0.0023 (13) | −0.0129 (11) |
C13 | 0.0459 (14) | 0.0544 (14) | 0.0460 (14) | −0.0059 (12) | −0.0007 (12) | −0.0088 (12) |
C14 | 0.0384 (13) | 0.0463 (12) | 0.0451 (14) | −0.0070 (10) | 0.0018 (11) | −0.0092 (11) |
C15 | 0.0441 (13) | 0.0446 (12) | 0.0379 (13) | −0.0044 (10) | 0.0042 (11) | −0.0057 (10) |
C16 | 0.0448 (14) | 0.0488 (13) | 0.0387 (14) | −0.0046 (11) | 0.0022 (11) | −0.0099 (10) |
C17 | 0.0397 (13) | 0.0415 (12) | 0.0387 (13) | −0.0025 (10) | −0.0011 (11) | 0.0006 (10) |
C18 | 0.0489 (15) | 0.0770 (17) | 0.0431 (16) | −0.0007 (13) | −0.0066 (12) | −0.0028 (13) |
C19 | 0.0555 (16) | 0.0774 (18) | 0.069 (2) | −0.0070 (14) | −0.0211 (15) | 0.0002 (16) |
C20 | 0.0377 (13) | 0.0622 (16) | 0.0669 (18) | −0.0006 (12) | −0.0045 (13) | −0.0085 (13) |
C21 | 0.0421 (14) | 0.0539 (14) | 0.0446 (15) | −0.0002 (11) | 0.0003 (12) | 0.0003 (12) |
C22 | 0.0450 (14) | 0.0426 (12) | 0.0349 (12) | −0.0002 (10) | 0.0024 (11) | 0.0008 (11) |
C23 | 0.0440 (14) | 0.0525 (13) | 0.0409 (13) | 0.0034 (11) | 0.0040 (11) | −0.0004 (12) |
C24 | 0.0660 (18) | 0.0543 (14) | 0.0402 (14) | 0.0061 (13) | 0.0126 (13) | −0.0003 (12) |
C25 | 0.077 (2) | 0.0652 (17) | 0.0418 (16) | −0.0102 (15) | 0.0101 (14) | −0.0149 (13) |
C26 | 0.0604 (17) | 0.0667 (16) | 0.0483 (16) | −0.0136 (14) | 0.0046 (14) | −0.0148 (14) |
C27 | 0.0474 (15) | 0.0477 (12) | 0.0352 (13) | −0.0044 (11) | 0.0021 (11) | −0.0034 (11) |
Cl1 | 0.0815 (5) | 0.0924 (5) | 0.0641 (5) | 0.0260 (4) | 0.0160 (4) | −0.0179 (4) |
N1 | 0.0360 (10) | 0.0531 (11) | 0.0388 (12) | −0.0023 (9) | −0.0029 (9) | −0.0026 (9) |
N2 | 0.0433 (11) | 0.0564 (11) | 0.0419 (11) | −0.0084 (9) | 0.0028 (10) | −0.0062 (10) |
O1 | 0.0604 (12) | 0.0985 (15) | 0.0491 (13) | −0.0232 (11) | −0.0054 (10) | 0.0164 (11) |
C1—C2 | 1.408 (3) | C16—C17 | 1.365 (3) |
C1—C6 | 1.418 (3) | C16—H16 | 0.9300 |
C1—C14 | 1.445 (3) | C17—C22 | 1.414 (3) |
C2—C3 | 1.361 (3) | C17—N1 | 1.422 (3) |
C2—H2 | 0.9300 | C18—N1 | 1.453 (3) |
C3—C4 | 1.388 (4) | C18—C19 | 1.513 (4) |
C3—H3 | 0.9300 | C18—H18A | 0.9700 |
C4—C5 | 1.359 (4) | C18—H18B | 0.9700 |
C4—H4 | 0.9300 | C19—C20 | 1.499 (4) |
C5—C6 | 1.402 (4) | C19—H19A | 0.9700 |
C5—H5 | 0.9300 | C19—H19B | 0.9700 |
C6—C7 | 1.461 (4) | C20—C21 | 1.495 (3) |
C7—C12 | 1.402 (4) | C20—H20A | 0.9700 |
C7—C8 | 1.414 (4) | C20—H20B | 0.9700 |
C8—C9 | 1.365 (5) | C21—O1 | 1.212 (3) |
C8—H8 | 0.9300 | C21—N1 | 1.367 (3) |
C9—C10 | 1.384 (4) | C22—C23 | 1.411 (3) |
C9—H9 | 0.9300 | C22—C27 | 1.417 (3) |
C10—C11 | 1.368 (4) | C23—C24 | 1.364 (4) |
C10—H10 | 0.9300 | C23—H23 | 0.9300 |
C11—C12 | 1.407 (4) | C24—C25 | 1.396 (4) |
C11—H11 | 0.9300 | C24—Cl1 | 1.738 (3) |
C12—C13 | 1.433 (4) | C25—C26 | 1.357 (4) |
C13—C14 | 1.350 (3) | C25—H25 | 0.9300 |
C13—H13 | 0.9300 | C26—C27 | 1.415 (3) |
C14—C15 | 1.489 (3) | C26—H26 | 0.9300 |
C15—N2 | 1.311 (3) | C27—N2 | 1.368 (3) |
C15—C16 | 1.419 (3) | ||
C2—C1—C6 | 118.2 (2) | C15—C16—H16 | 119.9 |
C2—C1—C14 | 122.3 (2) | C16—C17—C22 | 118.5 (2) |
C6—C1—C14 | 119.4 (2) | C16—C17—N1 | 120.5 (2) |
C3—C2—C1 | 121.6 (3) | C22—C17—N1 | 120.9 (2) |
C3—C2—H2 | 119.2 | N1—C18—C19 | 104.8 (2) |
C1—C2—H2 | 119.2 | N1—C18—H18A | 110.8 |
C2—C3—C4 | 119.7 (3) | C19—C18—H18A | 110.8 |
C2—C3—H3 | 120.2 | N1—C18—H18B | 110.8 |
C4—C3—H3 | 120.2 | C19—C18—H18B | 110.8 |
C5—C4—C3 | 120.5 (3) | H18A—C18—H18B | 108.9 |
C5—C4—H4 | 119.7 | C20—C19—C18 | 106.4 (2) |
C3—C4—H4 | 119.7 | C20—C19—H19A | 110.4 |
C4—C5—C6 | 121.4 (3) | C18—C19—H19A | 110.4 |
C4—C5—H5 | 119.3 | C20—C19—H19B | 110.4 |
C6—C5—H5 | 119.3 | C18—C19—H19B | 110.4 |
C5—C6—C1 | 118.4 (2) | H19A—C19—H19B | 108.6 |
C5—C6—C7 | 122.2 (2) | C21—C20—C19 | 106.2 (2) |
C1—C6—C7 | 119.4 (2) | C21—C20—H20A | 110.5 |
C12—C7—C8 | 118.2 (3) | C19—C20—H20A | 110.5 |
C12—C7—C6 | 119.4 (2) | C21—C20—H20B | 110.5 |
C8—C7—C6 | 122.4 (3) | C19—C20—H20B | 110.5 |
C9—C8—C7 | 120.5 (3) | H20A—C20—H20B | 108.7 |
C9—C8—H8 | 119.8 | O1—C21—N1 | 125.9 (2) |
C7—C8—H8 | 119.8 | O1—C21—C20 | 125.6 (2) |
C8—C9—C10 | 121.1 (3) | N1—C21—C20 | 108.5 (2) |
C8—C9—H9 | 119.4 | C23—C22—C17 | 123.9 (2) |
C10—C9—H9 | 119.4 | C23—C22—C27 | 118.9 (2) |
C11—C10—C9 | 119.9 (3) | C17—C22—C27 | 117.0 (2) |
C11—C10—H10 | 120.0 | C24—C23—C22 | 119.3 (2) |
C9—C10—H10 | 120.0 | C24—C23—H23 | 120.4 |
C10—C11—C12 | 120.3 (3) | C22—C23—H23 | 120.4 |
C10—C11—H11 | 119.8 | C23—C24—C25 | 122.2 (2) |
C12—C11—H11 | 119.8 | C23—C24—Cl1 | 118.5 (2) |
C7—C12—C11 | 119.9 (3) | C25—C24—Cl1 | 119.2 (2) |
C7—C12—C13 | 119.2 (2) | C26—C25—C24 | 119.5 (2) |
C11—C12—C13 | 120.8 (3) | C26—C25—H25 | 120.2 |
C14—C13—C12 | 122.5 (2) | C24—C25—H25 | 120.2 |
C14—C13—H13 | 118.8 | C25—C26—C27 | 120.6 (3) |
C12—C13—H13 | 118.8 | C25—C26—H26 | 119.7 |
C13—C14—C1 | 120.1 (2) | C27—C26—H26 | 119.7 |
C13—C14—C15 | 117.9 (2) | N2—C27—C26 | 117.1 (2) |
C1—C14—C15 | 122.0 (2) | N2—C27—C22 | 123.5 (2) |
N2—C15—C16 | 122.9 (2) | C26—C27—C22 | 119.3 (2) |
N2—C15—C14 | 116.5 (2) | C21—N1—C17 | 124.7 (2) |
C16—C15—C14 | 120.63 (19) | C21—N1—C18 | 112.6 (2) |
C17—C16—C15 | 120.2 (2) | C17—N1—C18 | 121.7 (2) |
C17—C16—H16 | 119.9 | C15—N2—C27 | 117.5 (2) |
C6—C1—C2—C3 | −2.3 (3) | C14—C15—C16—C17 | −177.8 (2) |
C14—C1—C2—C3 | −179.4 (2) | C15—C16—C17—C22 | −4.2 (3) |
C1—C2—C3—C4 | −0.5 (4) | C15—C16—C17—N1 | 179.1 (2) |
C2—C3—C4—C5 | 2.6 (4) | N1—C18—C19—C20 | 10.3 (3) |
C3—C4—C5—C6 | −1.9 (4) | C18—C19—C20—C21 | −5.0 (3) |
C4—C5—C6—C1 | −1.0 (4) | C19—C20—C21—O1 | 177.2 (3) |
C4—C5—C6—C7 | 176.7 (2) | C19—C20—C21—N1 | −2.6 (3) |
C2—C1—C6—C5 | 3.0 (3) | C16—C17—C22—C23 | −169.9 (2) |
C14—C1—C6—C5 | −179.8 (2) | N1—C17—C22—C23 | 6.8 (3) |
C2—C1—C6—C7 | −174.8 (2) | C16—C17—C22—C27 | 6.1 (3) |
C14—C1—C6—C7 | 2.4 (3) | N1—C17—C22—C27 | −177.2 (2) |
C5—C6—C7—C12 | −178.2 (2) | C17—C22—C23—C24 | 177.1 (2) |
C1—C6—C7—C12 | −0.4 (3) | C27—C22—C23—C24 | 1.1 (3) |
C5—C6—C7—C8 | 1.1 (4) | C22—C23—C24—C25 | 2.3 (4) |
C1—C6—C7—C8 | 178.8 (2) | C22—C23—C24—Cl1 | −175.13 (18) |
C12—C7—C8—C9 | −0.6 (4) | C23—C24—C25—C26 | −3.0 (4) |
C6—C7—C8—C9 | −179.9 (3) | Cl1—C24—C25—C26 | 174.4 (2) |
C7—C8—C9—C10 | 0.0 (5) | C24—C25—C26—C27 | 0.2 (4) |
C8—C9—C10—C11 | 0.5 (5) | C25—C26—C27—N2 | −173.4 (2) |
C9—C10—C11—C12 | −0.5 (4) | C25—C26—C27—C22 | 3.2 (4) |
C8—C7—C12—C11 | 0.6 (4) | C23—C22—C27—N2 | 172.5 (2) |
C6—C7—C12—C11 | 179.9 (2) | C17—C22—C27—N2 | −3.7 (3) |
C8—C7—C12—C13 | 179.8 (2) | C23—C22—C27—C26 | −3.8 (3) |
C6—C7—C12—C13 | −0.9 (3) | C17—C22—C27—C26 | 180.0 (2) |
C10—C11—C12—C7 | 0.0 (4) | O1—C21—N1—C17 | −1.1 (4) |
C10—C11—C12—C13 | −179.3 (2) | C20—C21—N1—C17 | 178.7 (2) |
C7—C12—C13—C14 | 0.1 (3) | O1—C21—N1—C18 | −170.0 (3) |
C11—C12—C13—C14 | 179.4 (2) | C20—C21—N1—C18 | 9.9 (3) |
C12—C13—C14—C1 | 1.9 (3) | C16—C17—N1—C21 | −130.9 (2) |
C12—C13—C14—C15 | −178.1 (2) | C22—C17—N1—C21 | 52.5 (3) |
C2—C1—C14—C13 | 173.9 (2) | C16—C17—N1—C18 | 37.0 (3) |
C6—C1—C14—C13 | −3.1 (3) | C22—C17—N1—C18 | −139.6 (2) |
C2—C1—C14—C15 | −6.2 (3) | C19—C18—N1—C21 | −12.8 (3) |
C6—C1—C14—C15 | 176.8 (2) | C19—C18—N1—C17 | 178.0 (2) |
C13—C14—C15—N2 | −53.4 (3) | C16—C15—N2—C27 | 3.2 (3) |
C1—C14—C15—N2 | 126.6 (2) | C14—C15—N2—C27 | −179.5 (2) |
C13—C14—C15—C16 | 123.9 (2) | C26—C27—N2—C15 | 175.4 (2) |
C1—C14—C15—C16 | −56.0 (3) | C22—C27—N2—C15 | −0.9 (3) |
N2—C15—C16—C17 | −0.6 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
C5—H5···O1i | 0.93 | 2.45 | 3.358 (4) | 164 |
Symmetry code: (i) −x, −y+2, z+1/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
C5—H5···O1i | 0.93 | 2.45 | 3.358 (4) | 164 |
Symmetry code: (i) −x, −y+2, z+1/2. |
Experimental details
Crystal data | |
Chemical formula | C27H19ClN2O |
Mr | 422.89 |
Crystal system, space group | Orthorhombic, Pna21 |
Temperature (K) | 293 |
a, b, c (Å) | 14.824 (3), 8.2946 (17), 16.924 (3) |
V (Å3) | 2081.0 (7) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.21 |
Crystal size (mm) | 0.25 × 0.20 × 0.20 |
Data collection | |
Diffractometer | Bruker SMART APEXII CCD |
Absorption correction | Multi-scan (SADABS; Bruker, 2008) |
Tmin, Tmax | 0.952, 0.960 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 8128, 3530, 2845 |
Rint | 0.027 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.034, 0.093, 1.06 |
No. of reflections | 3530 |
No. of parameters | 280 |
No. of restraints | 1 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.15, −0.16 |
Absolute structure | Flack (1983) |
Absolute structure parameter | 0.11 (7) |
Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 2012), SHELXL97 and PLATON (Spek, 2009).
Acknowledgements
The authors thank Professor D. Velmurugan, Centre for Advanced Study in Crystallography and Biophysics, University of Madras, for providing data-collection facilities.
References
Amal Raj, A., Raghunathan, R., Sridevi Kumari, M. R. & Raman, N. (2003). Bioorg. Med. Chem. 11, 407–419. Web of Science PubMed Google Scholar
Bruker (2008). APEX2, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Padwa, A., Brodney, M. A., Liu, B., Satake, K. & Wu, T. (1999). J. Org. Chem. 64, 3595–3607. Web of Science CrossRef PubMed CAS 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
This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
A large number of natural products contain the quinoline and Pyrrolidine heterocycles, and they are found in numerous commercial products, including pharmaceuticals, fragrances and dyes (Padwa et al., 1999). Pyrrolidine derivatives are found to have anticonvulsant, antimicrobial and antifungal activities against various pathogens (Amal Raj et al., 2003).
The molecular structure of he title molecule is shown in Fig. 1. The phenyl ring adopts an almost planar conformation with a maximum deviation -0.162° for the Cl1 atom. The pyrrolindine ring adopts a twisted conformation on (N1/C18-C21) with puckering parameters of q2 =0.112 (3)Å and φ = 25.4 (15)°. This latter ring forms dihedral angles of 48.6 (12) and 49.26 (2)° with quinoline-phenanthren ring system and the pyrrolindine ring, respectively. The keto atom O1 deviate from the attached ring system of pyrrolindine by -0.128Å.
In the crystal packing, molecules are linked via C—H···O intermolecular hydrogen bonds forming a two dimension network lying parallel to the (100) plane (Table 1 and Fig.2).