organic compounds
2-Hydroxy-5-[(E)-2-methylbenzylidene]-8-(2-methylphenyl)-9-phenyl-3,10-diazahexacyclo[10.7.1.13,7.02,11.07,11.016,20]henicosa-1(20),12,14,16,18-pentaen-6-one
aDepartment of Chemistry, College of Sciences, King Saud University, PO Box 2455, Riyadh 11451, Saudi Arabia, bSchool of Chemical Sciences, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and cDepartment of Physics, The Madura College, Madurai 625 011, India
*Correspondence e-mail: ambujasureshj@yahoo.com
In the title compound, C40H34N2O2, the central piperidine ring adopts a half-chair conformation and the fused pyrrolidine rings adopt twisted envelope (with the C atom bearing the methylphenyl ring as the flap atom) and envelope (with the C atom bound to the N atom, common to the pyridinone and pyrrolidine rings being the flap atom) conformations. The molecular structure features weak intramolecular N—H⋯O and C—H⋯O interactions. In the crystal, O—H⋯O hydrogen bonds generate a C(7) chain along the b-axis direction. C—H⋯O interactions also occur.
Related literature
For hydrogen-bond motifs, see: Bernstein et al. (1995). For similar structures, see: Kumar et al. (2010, 2011, 2012). For the importance of pyrrolidine, see: Asano et al. (2000); Shorvon (2001); Watson et al. (2001); Winchester & Fleet (1992). For puckering parameters, see: Cremer & Pople (1975).
Experimental
Crystal data
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Refinement
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Data collection: APEX2 (Bruker, 2004); cell SAINT (Bruker, 2004); data reduction: SAINT; 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: SHELXL97.
Supporting information
10.1107/S160053681204648X/pk2453sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S160053681204648X/pk2453Isup2.hkl
Supporting information file. DOI: 10.1107/S160053681204648X/pk2453Isup3.cml
A mixture of 3,5-bis[(E)-(2-methylphenyl)methylidene]tetrahydro-4(1H)-pyridinone (1 mmol), acenaphthenequinone (1 mmol), and phenylglycine (1 mmol) were dissolved in methanol (5 ml) and refluxed in a water bath for 1 h. After completion of the reaction as evident from TLC, the mixture was poured into water (50 ml). The precipitated solid was filtered and washed with water to obtain the product which was further purified by recrystallization from ethyl acetate. Yield 89%, melting point 212–213°C
H atoms were placed at calculated positions and allowed to ride on their carrier atoms with C—H = 0.93–0.97 Å and O—H = 0.82 Å. Uiso = 1.2Ueq(C) for CH CH2 groups and Uiso = 1.5Ueq(C) for OH and CH3 groups.
Data collection: APEX2 (Bruker, 2004); cell
SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); 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: SHELXL97 (Sheldrick, 2008).C40H34N2O2 | F(000) = 1216 |
Mr = 574.69 | Dx = 1.304 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 2000 reflections |
a = 14.0679 (2) Å | θ = 2–31° |
b = 7.7245 (1) Å | µ = 0.08 mm−1 |
c = 26.9686 (3) Å | T = 293 K |
β = 92.596 (1)° | Block, colourless |
V = 2927.60 (7) Å3 | 0.21 × 0.15 × 0.13 mm |
Z = 4 |
Bruker Kappa APEXII diffractometer | 8777 independent reflections |
Radiation source: fine-focus sealed tube | 6575 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.047 |
Detector resolution: 0.2 pixels mm-1 | θmax = 30.4°, θmin = 1.5° |
ω and ϕ scans | h = −20→19 |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | k = −10→10 |
Tmin = 0.973, Tmax = 0.978 | l = −38→38 |
33520 measured reflections |
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)] = 0.054 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.137 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0605P)2 + 1.2845P] where P = (Fo2 + 2Fc2)/3 |
8777 reflections | (Δ/σ)max < 0.001 |
404 parameters | Δρmax = 0.48 e Å−3 |
0 restraints | Δρmin = −0.27 e Å−3 |
C40H34N2O2 | V = 2927.60 (7) Å3 |
Mr = 574.69 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 14.0679 (2) Å | µ = 0.08 mm−1 |
b = 7.7245 (1) Å | T = 293 K |
c = 26.9686 (3) Å | 0.21 × 0.15 × 0.13 mm |
β = 92.596 (1)° |
Bruker Kappa APEXII diffractometer | 8777 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 6575 reflections with I > 2σ(I) |
Tmin = 0.973, Tmax = 0.978 | Rint = 0.047 |
33520 measured reflections |
R[F2 > 2σ(F2)] = 0.054 | 0 restraints |
wR(F2) = 0.137 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.02 | Δρmax = 0.48 e Å−3 |
8777 reflections | Δρmin = −0.27 e Å−3 |
404 parameters |
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 | ||
H2A | 0.1618 (13) | −0.048 (3) | 0.1407 (7) | 0.021 (5)* | |
C1 | −0.08779 (9) | 0.3112 (2) | 0.19923 (5) | 0.0140 (3) | |
H1A | −0.0948 | 0.3696 | 0.2307 | 0.017* | |
H1B | −0.1485 | 0.2587 | 0.1897 | 0.017* | |
C2 | −0.06395 (9) | 0.4456 (2) | 0.16030 (5) | 0.0138 (3) | |
C3 | 0.03856 (9) | 0.4691 (2) | 0.14943 (4) | 0.0130 (3) | |
C4 | 0.10336 (9) | 0.31845 (19) | 0.16240 (5) | 0.0120 (3) | |
C5 | 0.20821 (9) | 0.34675 (19) | 0.15125 (5) | 0.0123 (3) | |
H5 | 0.2092 | 0.3925 | 0.1174 | 0.015* | |
C6 | 0.24693 (9) | 0.1597 (2) | 0.14945 (5) | 0.0136 (3) | |
H6 | 0.2609 | 0.1174 | 0.1833 | 0.016* | |
C7 | 0.07621 (9) | 0.15392 (19) | 0.13098 (5) | 0.0116 (3) | |
C8 | −0.00249 (9) | 0.06007 (19) | 0.16306 (5) | 0.0124 (3) | |
C9 | 0.07764 (9) | 0.2551 (2) | 0.21505 (5) | 0.0139 (3) | |
H9A | 0.1241 | 0.1725 | 0.2282 | 0.017* | |
H9B | 0.0740 | 0.3515 | 0.2379 | 0.017* | |
C10 | −0.08848 (9) | 0.0412 (2) | 0.12769 (5) | 0.0135 (3) | |
C11 | −0.06725 (9) | 0.1136 (2) | 0.08159 (5) | 0.0133 (3) | |
C12 | 0.02524 (9) | 0.18289 (19) | 0.08079 (5) | 0.0127 (3) | |
C13 | 0.05395 (10) | 0.2586 (2) | 0.03803 (5) | 0.0167 (3) | |
H13 | 0.1141 | 0.3078 | 0.0367 | 0.020* | |
C14 | −0.01019 (11) | 0.2604 (2) | −0.00437 (5) | 0.0202 (3) | |
H14 | 0.0096 | 0.3098 | −0.0336 | 0.024* | |
C15 | −0.10010 (10) | 0.1918 (2) | −0.00362 (5) | 0.0196 (3) | |
H15 | −0.1397 | 0.1938 | −0.0322 | 0.024* | |
C16 | −0.13281 (10) | 0.1180 (2) | 0.04057 (5) | 0.0163 (3) | |
C17 | −0.22466 (10) | 0.0493 (2) | 0.04838 (5) | 0.0201 (3) | |
H17 | −0.2712 | 0.0515 | 0.0228 | 0.024* | |
C18 | −0.24517 (10) | −0.0208 (2) | 0.09376 (6) | 0.0206 (3) | |
H18 | −0.3058 | −0.0645 | 0.0981 | 0.025* | |
C19 | −0.17692 (10) | −0.0282 (2) | 0.13393 (5) | 0.0170 (3) | |
H19 | −0.1917 | −0.0790 | 0.1639 | 0.020* | |
C21 | −0.12729 (9) | 0.5353 (2) | 0.13163 (5) | 0.0152 (3) | |
H21 | −0.1016 | 0.6046 | 0.1074 | 0.018* | |
C22 | −0.23170 (9) | 0.5386 (2) | 0.13336 (5) | 0.0159 (3) | |
C23 | −0.27629 (10) | 0.5428 (2) | 0.17870 (5) | 0.0184 (3) | |
H23 | −0.2399 | 0.5296 | 0.2081 | 0.022* | |
C24 | −0.37414 (10) | 0.5663 (2) | 0.18048 (6) | 0.0233 (3) | |
H24 | −0.4026 | 0.5730 | 0.2109 | 0.028* | |
C25 | −0.42886 (10) | 0.5797 (2) | 0.13671 (6) | 0.0257 (4) | |
H25 | −0.4944 | 0.5943 | 0.1376 | 0.031* | |
C26 | −0.38589 (10) | 0.5714 (2) | 0.09141 (6) | 0.0235 (3) | |
H26 | −0.4235 | 0.5781 | 0.0622 | 0.028* | |
C27 | −0.28759 (10) | 0.5533 (2) | 0.08876 (5) | 0.0181 (3) | |
C28 | −0.24307 (11) | 0.5548 (3) | 0.03907 (5) | 0.0240 (3) | |
H28A | −0.2917 | 0.5402 | 0.0133 | 0.036* | |
H28B | −0.1979 | 0.4620 | 0.0376 | 0.036* | |
H28C | −0.2112 | 0.6633 | 0.0346 | 0.036* | |
C51 | 0.26791 (9) | 0.4681 (2) | 0.18393 (5) | 0.0144 (3) | |
C52 | 0.28521 (10) | 0.4299 (2) | 0.23427 (5) | 0.0195 (3) | |
H52 | 0.2572 | 0.3323 | 0.2476 | 0.023* | |
C53 | 0.34327 (11) | 0.5341 (3) | 0.26488 (6) | 0.0245 (4) | |
H53 | 0.3548 | 0.5050 | 0.2981 | 0.029* | |
C54 | 0.38370 (11) | 0.6815 (2) | 0.24562 (6) | 0.0242 (3) | |
H54 | 0.4216 | 0.7533 | 0.2659 | 0.029* | |
C55 | 0.36716 (10) | 0.7212 (2) | 0.19578 (6) | 0.0215 (3) | |
H55 | 0.3942 | 0.8206 | 0.1830 | 0.026* | |
C56 | 0.31087 (9) | 0.6156 (2) | 0.16419 (5) | 0.0162 (3) | |
C57 | 0.30179 (10) | 0.6591 (2) | 0.10950 (5) | 0.0214 (3) | |
H57A | 0.3332 | 0.7671 | 0.1037 | 0.032* | |
H57B | 0.2357 | 0.6686 | 0.0993 | 0.032* | |
H57C | 0.3307 | 0.5692 | 0.0908 | 0.032* | |
C61 | 0.33606 (9) | 0.1507 (2) | 0.11991 (5) | 0.0140 (3) | |
C62 | 0.42569 (10) | 0.1631 (2) | 0.14398 (5) | 0.0176 (3) | |
H62 | 0.4307 | 0.1691 | 0.1784 | 0.021* | |
C63 | 0.50781 (10) | 0.1664 (2) | 0.11694 (6) | 0.0216 (3) | |
H63 | 0.5672 | 0.1750 | 0.1334 | 0.026* | |
C64 | 0.50103 (10) | 0.1570 (2) | 0.06563 (6) | 0.0222 (3) | |
H64 | 0.5558 | 0.1591 | 0.0475 | 0.027* | |
C65 | 0.41180 (10) | 0.1444 (2) | 0.04118 (5) | 0.0211 (3) | |
H65 | 0.4069 | 0.1382 | 0.0067 | 0.025* | |
C66 | 0.33007 (10) | 0.1409 (2) | 0.06832 (5) | 0.0176 (3) | |
H66 | 0.2708 | 0.1319 | 0.0518 | 0.021* | |
N1 | −0.01604 (8) | 0.17311 (17) | 0.20624 (4) | 0.0136 (2) | |
N2 | 0.16681 (8) | 0.06105 (18) | 0.12630 (4) | 0.0148 (2) | |
O1 | 0.06835 (7) | 0.60208 (15) | 0.13039 (4) | 0.0166 (2) | |
O2 | 0.03037 (7) | −0.09871 (14) | 0.18344 (3) | 0.0162 (2) | |
H2 | 0.0298 | −0.1727 | 0.1616 | 0.024* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0134 (5) | 0.0153 (7) | 0.0134 (6) | 0.0008 (5) | 0.0025 (4) | −0.0012 (5) |
C2 | 0.0136 (5) | 0.0135 (7) | 0.0143 (6) | −0.0004 (5) | 0.0016 (4) | −0.0029 (5) |
C3 | 0.0138 (5) | 0.0159 (7) | 0.0092 (5) | −0.0001 (5) | 0.0002 (4) | −0.0025 (5) |
C4 | 0.0118 (5) | 0.0132 (7) | 0.0108 (5) | 0.0000 (5) | 0.0002 (4) | −0.0006 (5) |
C5 | 0.0117 (5) | 0.0135 (7) | 0.0119 (5) | 0.0002 (5) | 0.0002 (4) | −0.0007 (5) |
C6 | 0.0121 (5) | 0.0158 (7) | 0.0127 (5) | 0.0008 (5) | −0.0003 (4) | 0.0000 (5) |
C7 | 0.0116 (5) | 0.0122 (7) | 0.0109 (5) | 0.0004 (5) | 0.0007 (4) | −0.0009 (5) |
C8 | 0.0134 (5) | 0.0130 (7) | 0.0109 (5) | −0.0002 (5) | 0.0014 (4) | 0.0005 (5) |
C9 | 0.0143 (5) | 0.0166 (7) | 0.0109 (5) | −0.0003 (5) | 0.0005 (4) | −0.0016 (5) |
C10 | 0.0137 (5) | 0.0126 (7) | 0.0142 (6) | 0.0008 (5) | 0.0003 (4) | −0.0016 (5) |
C11 | 0.0148 (5) | 0.0131 (7) | 0.0121 (5) | 0.0010 (5) | 0.0004 (4) | −0.0024 (5) |
C12 | 0.0146 (5) | 0.0121 (7) | 0.0115 (5) | 0.0012 (5) | 0.0006 (4) | −0.0021 (5) |
C13 | 0.0171 (6) | 0.0188 (8) | 0.0143 (6) | −0.0002 (6) | 0.0027 (5) | −0.0002 (6) |
C14 | 0.0259 (7) | 0.0240 (9) | 0.0109 (6) | 0.0033 (7) | 0.0018 (5) | 0.0017 (6) |
C15 | 0.0239 (7) | 0.0224 (8) | 0.0122 (6) | 0.0059 (6) | −0.0034 (5) | −0.0011 (6) |
C16 | 0.0173 (6) | 0.0162 (7) | 0.0151 (6) | 0.0025 (6) | −0.0021 (5) | −0.0039 (6) |
C17 | 0.0159 (6) | 0.0220 (9) | 0.0218 (7) | 0.0012 (6) | −0.0048 (5) | −0.0062 (6) |
C18 | 0.0147 (6) | 0.0216 (8) | 0.0255 (7) | −0.0025 (6) | 0.0006 (5) | −0.0049 (6) |
C19 | 0.0169 (6) | 0.0167 (7) | 0.0175 (6) | −0.0023 (6) | 0.0038 (5) | −0.0022 (6) |
C21 | 0.0137 (6) | 0.0158 (7) | 0.0163 (6) | 0.0006 (6) | 0.0020 (4) | −0.0006 (6) |
C22 | 0.0138 (6) | 0.0144 (7) | 0.0197 (6) | 0.0007 (6) | 0.0016 (5) | −0.0003 (6) |
C23 | 0.0178 (6) | 0.0180 (8) | 0.0198 (6) | 0.0013 (6) | 0.0033 (5) | 0.0000 (6) |
C24 | 0.0186 (6) | 0.0236 (9) | 0.0282 (7) | 0.0004 (6) | 0.0080 (5) | −0.0007 (7) |
C25 | 0.0138 (6) | 0.0261 (9) | 0.0373 (9) | 0.0003 (6) | 0.0031 (6) | 0.0000 (7) |
C26 | 0.0167 (6) | 0.0239 (9) | 0.0293 (8) | −0.0004 (6) | −0.0043 (5) | 0.0018 (7) |
C27 | 0.0163 (6) | 0.0163 (8) | 0.0215 (7) | 0.0008 (6) | −0.0004 (5) | 0.0009 (6) |
C28 | 0.0237 (7) | 0.0296 (10) | 0.0187 (7) | 0.0060 (7) | 0.0003 (5) | 0.0008 (7) |
C51 | 0.0117 (5) | 0.0157 (7) | 0.0158 (6) | −0.0001 (5) | 0.0009 (4) | −0.0035 (5) |
C52 | 0.0183 (6) | 0.0236 (8) | 0.0165 (6) | −0.0053 (6) | 0.0004 (5) | −0.0009 (6) |
C53 | 0.0227 (7) | 0.0336 (10) | 0.0170 (6) | −0.0058 (7) | −0.0006 (5) | −0.0054 (7) |
C54 | 0.0197 (6) | 0.0270 (9) | 0.0256 (7) | −0.0039 (7) | −0.0016 (5) | −0.0110 (7) |
C55 | 0.0174 (6) | 0.0176 (8) | 0.0296 (8) | −0.0025 (6) | 0.0007 (5) | −0.0030 (7) |
C56 | 0.0127 (5) | 0.0156 (7) | 0.0203 (6) | 0.0012 (6) | 0.0015 (5) | −0.0012 (6) |
C57 | 0.0201 (6) | 0.0212 (8) | 0.0227 (7) | −0.0030 (6) | −0.0003 (5) | 0.0056 (6) |
C61 | 0.0123 (5) | 0.0129 (7) | 0.0167 (6) | 0.0017 (5) | 0.0001 (4) | 0.0000 (5) |
C62 | 0.0157 (6) | 0.0200 (8) | 0.0169 (6) | 0.0008 (6) | −0.0013 (5) | 0.0001 (6) |
C63 | 0.0126 (6) | 0.0255 (9) | 0.0265 (7) | 0.0003 (6) | −0.0011 (5) | −0.0006 (7) |
C64 | 0.0159 (6) | 0.0252 (9) | 0.0260 (7) | 0.0004 (6) | 0.0064 (5) | −0.0039 (7) |
C65 | 0.0205 (6) | 0.0260 (9) | 0.0172 (6) | 0.0006 (7) | 0.0038 (5) | −0.0035 (6) |
C66 | 0.0148 (6) | 0.0221 (8) | 0.0158 (6) | 0.0006 (6) | −0.0002 (5) | −0.0023 (6) |
N1 | 0.0140 (5) | 0.0158 (6) | 0.0109 (5) | −0.0001 (5) | 0.0009 (4) | −0.0016 (5) |
N2 | 0.0119 (5) | 0.0143 (6) | 0.0183 (5) | 0.0006 (5) | 0.0005 (4) | −0.0024 (5) |
O1 | 0.0160 (4) | 0.0152 (5) | 0.0188 (5) | 0.0001 (4) | 0.0024 (3) | 0.0014 (4) |
O2 | 0.0228 (5) | 0.0121 (5) | 0.0137 (4) | 0.0018 (4) | 0.0008 (4) | 0.0007 (4) |
C1—N1 | 1.4750 (18) | C21—C22 | 1.4720 (18) |
C1—C2 | 1.524 (2) | C21—H21 | 0.9300 |
C1—H1A | 0.9700 | C22—C23 | 1.3997 (19) |
C1—H1B | 0.9700 | C22—C27 | 1.4113 (19) |
C2—C21 | 1.3451 (19) | C23—C24 | 1.3916 (19) |
C2—C3 | 1.4956 (17) | C23—H23 | 0.9300 |
C3—O1 | 1.2303 (18) | C24—C25 | 1.384 (2) |
C3—C4 | 1.510 (2) | C24—H24 | 0.9300 |
C4—C5 | 1.5343 (17) | C25—C26 | 1.389 (2) |
C4—C9 | 1.5598 (18) | C25—H25 | 0.9300 |
C4—C7 | 1.565 (2) | C26—C27 | 1.3950 (19) |
C5—C51 | 1.5146 (19) | C26—H26 | 0.9300 |
C5—C6 | 1.546 (2) | C27—C28 | 1.505 (2) |
C5—H5 | 0.9800 | C28—H28A | 0.9600 |
C6—N2 | 1.4757 (18) | C28—H28B | 0.9600 |
C6—C61 | 1.5173 (18) | C28—H28C | 0.9600 |
C6—H6 | 0.9800 | C51—C52 | 1.3997 (19) |
C7—N2 | 1.4730 (17) | C51—C56 | 1.405 (2) |
C7—C12 | 1.5192 (18) | C52—C53 | 1.391 (2) |
C7—C8 | 1.6082 (18) | C52—H52 | 0.9300 |
C8—O2 | 1.4131 (17) | C53—C54 | 1.384 (3) |
C8—N1 | 1.4747 (17) | C53—H53 | 0.9300 |
C8—C10 | 1.5133 (18) | C54—C55 | 1.388 (2) |
C9—N1 | 1.4718 (17) | C54—H54 | 0.9300 |
C9—H9A | 0.9700 | C55—C56 | 1.399 (2) |
C9—H9B | 0.9700 | C55—H55 | 0.9300 |
C10—C19 | 1.3721 (18) | C56—C57 | 1.512 (2) |
C10—C11 | 1.4073 (18) | C57—H57A | 0.9600 |
C11—C12 | 1.4082 (18) | C57—H57B | 0.9600 |
C11—C16 | 1.4083 (18) | C57—H57C | 0.9600 |
C12—C13 | 1.3703 (18) | C61—C66 | 1.3921 (18) |
C13—C14 | 1.4241 (19) | C61—C62 | 1.3951 (18) |
C13—H13 | 0.9300 | C62—C63 | 1.3940 (19) |
C14—C15 | 1.372 (2) | C62—H62 | 0.9300 |
C14—H14 | 0.9300 | C63—C64 | 1.385 (2) |
C15—C16 | 1.417 (2) | C63—H63 | 0.9300 |
C15—H15 | 0.9300 | C64—C65 | 1.395 (2) |
C16—C17 | 1.421 (2) | C64—H64 | 0.9300 |
C17—C18 | 1.380 (2) | C65—C66 | 1.3910 (19) |
C17—H17 | 0.9300 | C65—H65 | 0.9300 |
C18—C19 | 1.416 (2) | C66—H66 | 0.9300 |
C18—H18 | 0.9300 | N2—H2A | 0.93 (2) |
C19—H19 | 0.9300 | O2—H2 | 0.8200 |
N1—C1—C2 | 114.20 (10) | C18—C19—H19 | 120.7 |
N1—C1—H1A | 108.7 | C2—C21—C22 | 128.81 (13) |
C2—C1—H1A | 108.7 | C2—C21—H21 | 115.6 |
N1—C1—H1B | 108.7 | C22—C21—H21 | 115.6 |
C2—C1—H1B | 108.7 | C23—C22—C27 | 119.23 (13) |
H1A—C1—H1B | 107.6 | C23—C22—C21 | 121.02 (13) |
C21—C2—C3 | 116.37 (12) | C27—C22—C21 | 119.51 (12) |
C21—C2—C1 | 125.87 (12) | C24—C23—C22 | 121.09 (14) |
C3—C2—C1 | 117.52 (12) | C24—C23—H23 | 119.5 |
O1—C3—C2 | 122.21 (13) | C22—C23—H23 | 119.5 |
O1—C3—C4 | 121.78 (12) | C25—C24—C23 | 119.56 (14) |
C2—C3—C4 | 116.00 (12) | C25—C24—H24 | 120.2 |
C3—C4—C5 | 114.87 (12) | C23—C24—H24 | 120.2 |
C3—C4—C9 | 106.86 (10) | C24—C25—C26 | 119.97 (14) |
C5—C4—C9 | 119.19 (10) | C24—C25—H25 | 120.0 |
C3—C4—C7 | 111.75 (10) | C26—C25—H25 | 120.0 |
C5—C4—C7 | 102.88 (10) | C25—C26—C27 | 121.44 (14) |
C9—C4—C7 | 100.20 (11) | C25—C26—H26 | 119.3 |
C51—C5—C4 | 119.13 (11) | C27—C26—H26 | 119.3 |
C51—C5—C6 | 114.20 (11) | C26—C27—C22 | 118.67 (13) |
C4—C5—C6 | 102.49 (11) | C26—C27—C28 | 119.89 (13) |
C51—C5—H5 | 106.7 | C22—C27—C28 | 121.42 (12) |
C4—C5—H5 | 106.7 | C27—C28—H28A | 109.5 |
C6—C5—H5 | 106.7 | C27—C28—H28B | 109.5 |
N2—C6—C61 | 112.81 (11) | H28A—C28—H28B | 109.5 |
N2—C6—C5 | 103.45 (10) | C27—C28—H28C | 109.5 |
C61—C6—C5 | 111.10 (12) | H28A—C28—H28C | 109.5 |
N2—C6—H6 | 109.8 | H28B—C28—H28C | 109.5 |
C61—C6—H6 | 109.8 | C52—C51—C56 | 118.67 (13) |
C5—C6—H6 | 109.8 | C52—C51—C5 | 120.07 (13) |
N2—C7—C12 | 111.75 (10) | C56—C51—C5 | 121.18 (12) |
N2—C7—C4 | 104.53 (10) | C53—C52—C51 | 121.65 (15) |
C12—C7—C4 | 117.16 (12) | C53—C52—H52 | 119.2 |
N2—C7—C8 | 116.49 (12) | C51—C52—H52 | 119.2 |
C12—C7—C8 | 103.71 (10) | C54—C53—C52 | 119.58 (15) |
C4—C7—C8 | 103.41 (10) | C54—C53—H53 | 120.2 |
O2—C8—N1 | 104.98 (10) | C52—C53—H53 | 120.2 |
O2—C8—C10 | 113.56 (12) | C53—C54—C55 | 119.42 (15) |
N1—C8—C10 | 115.24 (11) | C53—C54—H54 | 120.3 |
O2—C8—C7 | 112.30 (10) | C55—C54—H54 | 120.3 |
N1—C8—C7 | 105.94 (11) | C54—C55—C56 | 121.76 (16) |
C10—C8—C7 | 104.74 (10) | C54—C55—H55 | 119.1 |
N1—C9—C4 | 103.36 (10) | C56—C55—H55 | 119.1 |
N1—C9—H9A | 111.1 | C55—C56—C51 | 118.88 (13) |
C4—C9—H9A | 111.1 | C55—C56—C57 | 118.99 (14) |
N1—C9—H9B | 111.1 | C51—C56—C57 | 122.07 (13) |
C4—C9—H9B | 111.1 | C56—C57—H57A | 109.5 |
H9A—C9—H9B | 109.1 | C56—C57—H57B | 109.5 |
C19—C10—C11 | 119.56 (12) | H57A—C57—H57B | 109.5 |
C19—C10—C8 | 131.59 (12) | C56—C57—H57C | 109.5 |
C11—C10—C8 | 108.84 (11) | H57A—C57—H57C | 109.5 |
C10—C11—C12 | 113.44 (12) | H57B—C57—H57C | 109.5 |
C10—C11—C16 | 123.08 (12) | C66—C61—C62 | 118.77 (12) |
C12—C11—C16 | 123.47 (13) | C66—C61—C6 | 120.88 (12) |
C13—C12—C11 | 118.88 (12) | C62—C61—C6 | 120.24 (12) |
C13—C12—C7 | 131.88 (12) | C63—C62—C61 | 120.72 (13) |
C11—C12—C7 | 109.24 (11) | C63—C62—H62 | 119.6 |
C12—C13—C14 | 118.67 (13) | C61—C62—H62 | 119.6 |
C12—C13—H13 | 120.7 | C64—C63—C62 | 120.04 (13) |
C14—C13—H13 | 120.7 | C64—C63—H63 | 120.0 |
C15—C14—C13 | 122.37 (13) | C62—C63—H63 | 120.0 |
C15—C14—H14 | 118.8 | C63—C64—C65 | 119.74 (13) |
C13—C14—H14 | 118.8 | C63—C64—H64 | 120.1 |
C14—C15—C16 | 120.16 (13) | C65—C64—H64 | 120.1 |
C14—C15—H15 | 119.9 | C66—C65—C64 | 120.01 (13) |
C16—C15—H15 | 119.9 | C66—C65—H65 | 120.0 |
C11—C16—C15 | 116.39 (13) | C64—C65—H65 | 120.0 |
C11—C16—C17 | 116.23 (13) | C65—C66—C61 | 120.73 (13) |
C15—C16—C17 | 127.38 (13) | C65—C66—H66 | 119.6 |
C18—C17—C16 | 120.37 (13) | C61—C66—H66 | 119.6 |
C18—C17—H17 | 119.8 | C9—N1—C8 | 103.62 (10) |
C16—C17—H17 | 119.8 | C9—N1—C1 | 108.17 (12) |
C17—C18—C19 | 122.17 (13) | C8—N1—C1 | 116.07 (10) |
C17—C18—H18 | 118.9 | C7—N2—C6 | 111.07 (11) |
C19—C18—H18 | 118.9 | C7—N2—H2A | 108.8 (11) |
C10—C19—C18 | 118.53 (13) | C6—N2—H2A | 111.1 (11) |
C10—C19—H19 | 120.7 | C8—O2—H2 | 109.5 |
N1—C1—C2—C21 | 149.63 (14) | C12—C11—C16—C15 | 2.2 (2) |
N1—C1—C2—C3 | −24.42 (17) | C10—C11—C16—C17 | 1.9 (2) |
C21—C2—C3—O1 | 26.7 (2) | C12—C11—C16—C17 | −177.20 (14) |
C1—C2—C3—O1 | −158.71 (13) | C14—C15—C16—C11 | −2.5 (2) |
C21—C2—C3—C4 | −152.30 (13) | C14—C15—C16—C17 | 176.78 (16) |
C1—C2—C3—C4 | 22.32 (17) | C11—C16—C17—C18 | −1.6 (2) |
O1—C3—C4—C5 | 1.50 (18) | C15—C16—C17—C18 | 179.11 (16) |
C2—C3—C4—C5 | −179.52 (11) | C16—C17—C18—C19 | −0.3 (3) |
O1—C3—C4—C9 | 136.12 (13) | C11—C10—C19—C18 | −1.5 (2) |
C2—C3—C4—C9 | −44.91 (15) | C8—C10—C19—C18 | 177.39 (15) |
O1—C3—C4—C7 | −115.20 (14) | C17—C18—C19—C10 | 1.9 (2) |
C2—C3—C4—C7 | 63.77 (14) | C3—C2—C21—C22 | 179.94 (14) |
C3—C4—C5—C51 | 72.82 (15) | C1—C2—C21—C22 | 5.8 (3) |
C9—C4—C5—C51 | −55.89 (19) | C2—C21—C22—C23 | 41.3 (2) |
C7—C4—C5—C51 | −165.51 (12) | C2—C21—C22—C27 | −144.41 (17) |
C3—C4—C5—C6 | −160.01 (11) | C27—C22—C23—C24 | −1.9 (2) |
C9—C4—C5—C6 | 71.28 (15) | C21—C22—C23—C24 | 172.40 (15) |
C7—C4—C5—C6 | −38.34 (12) | C22—C23—C24—C25 | 2.3 (3) |
C51—C5—C6—N2 | 166.72 (10) | C23—C24—C25—C26 | −0.7 (3) |
C4—C5—C6—N2 | 36.46 (12) | C24—C25—C26—C27 | −1.4 (3) |
C51—C5—C6—C61 | −71.98 (14) | C25—C26—C27—C22 | 1.7 (3) |
C4—C5—C6—C61 | 157.77 (10) | C25—C26—C27—C28 | −176.57 (17) |
C3—C4—C7—N2 | 149.97 (11) | C23—C22—C27—C26 | −0.1 (2) |
C5—C4—C7—N2 | 26.21 (13) | C21—C22—C27—C26 | −174.49 (15) |
C9—C4—C7—N2 | −97.13 (11) | C23—C22—C27—C28 | 178.19 (16) |
C3—C4—C7—C12 | 25.69 (15) | C21—C22—C27—C28 | 3.8 (2) |
C5—C4—C7—C12 | −98.08 (12) | C4—C5—C51—C52 | 63.48 (18) |
C9—C4—C7—C12 | 138.59 (11) | C6—C5—C51—C52 | −57.98 (16) |
C3—C4—C7—C8 | −87.65 (12) | C4—C5—C51—C56 | −119.80 (14) |
C5—C4—C7—C8 | 148.58 (10) | C6—C5—C51—C56 | 118.73 (14) |
C9—C4—C7—C8 | 25.25 (12) | C56—C51—C52—C53 | 0.2 (2) |
N2—C7—C8—O2 | 1.91 (16) | C5—C51—C52—C53 | 177.00 (14) |
C12—C7—C8—O2 | 125.13 (11) | C51—C52—C53—C54 | 1.3 (2) |
C4—C7—C8—O2 | −112.11 (12) | C52—C53—C54—C55 | −1.2 (2) |
N2—C7—C8—N1 | 115.97 (12) | C53—C54—C55—C56 | −0.3 (2) |
C12—C7—C8—N1 | −120.81 (11) | C54—C55—C56—C51 | 1.8 (2) |
C4—C7—C8—N1 | 1.96 (13) | C54—C55—C56—C57 | −175.45 (14) |
N2—C7—C8—C10 | −121.77 (12) | C52—C51—C56—C55 | −1.7 (2) |
C12—C7—C8—C10 | 1.45 (14) | C5—C51—C56—C55 | −178.49 (13) |
C4—C7—C8—C10 | 124.21 (11) | C52—C51—C56—C57 | 175.45 (13) |
C3—C4—C9—N1 | 71.24 (13) | C5—C51—C56—C57 | −1.3 (2) |
C5—C4—C9—N1 | −156.48 (12) | N2—C6—C61—C66 | 33.4 (2) |
C7—C4—C9—N1 | −45.38 (13) | C5—C6—C61—C66 | −82.26 (17) |
O2—C8—C10—C19 | 57.4 (2) | N2—C6—C61—C62 | −150.62 (14) |
N1—C8—C10—C19 | −63.8 (2) | C5—C6—C61—C62 | 93.74 (16) |
C7—C8—C10—C19 | −179.77 (16) | C66—C61—C62—C63 | 0.3 (2) |
O2—C8—C10—C11 | −123.63 (13) | C6—C61—C62—C63 | −175.75 (15) |
N1—C8—C10—C11 | 115.22 (13) | C61—C62—C63—C64 | −0.2 (3) |
C7—C8—C10—C11 | −0.75 (15) | C62—C63—C64—C65 | 0.1 (3) |
C19—C10—C11—C12 | 178.83 (14) | C63—C64—C65—C66 | −0.1 (3) |
C8—C10—C11—C12 | −0.32 (17) | C64—C65—C66—C61 | 0.3 (3) |
C19—C10—C11—C16 | −0.4 (2) | C62—C61—C66—C65 | −0.4 (2) |
C8—C10—C11—C16 | −179.54 (13) | C6—C61—C66—C65 | 175.66 (15) |
C10—C11—C12—C13 | −179.37 (14) | C4—C9—N1—C8 | 48.13 (13) |
C16—C11—C12—C13 | −0.2 (2) | C4—C9—N1—C1 | −75.60 (12) |
C10—C11—C12—C7 | 1.34 (17) | O2—C8—N1—C9 | 88.49 (12) |
C16—C11—C12—C7 | −179.45 (13) | C10—C8—N1—C9 | −145.81 (12) |
N2—C7—C12—C13 | −54.6 (2) | C7—C8—N1—C9 | −30.52 (13) |
C4—C7—C12—C13 | 66.0 (2) | O2—C8—N1—C1 | −153.10 (11) |
C8—C7—C12—C13 | 179.16 (16) | C10—C8—N1—C1 | −27.41 (16) |
N2—C7—C12—C11 | 124.59 (13) | C7—C8—N1—C1 | 87.88 (13) |
C4—C7—C12—C11 | −114.86 (13) | C2—C1—N1—C9 | 52.05 (14) |
C8—C7—C12—C11 | −1.68 (15) | C2—C1—N1—C8 | −63.82 (15) |
C11—C12—C13—C14 | −1.5 (2) | C12—C7—N2—C6 | 124.29 (12) |
C7—C12—C13—C14 | 177.57 (15) | C4—C7—N2—C6 | −3.38 (14) |
C12—C13—C14—C15 | 1.2 (2) | C8—C7—N2—C6 | −116.76 (13) |
C13—C14—C15—C16 | 1.0 (3) | C61—C6—N2—C7 | −140.82 (12) |
C10—C11—C16—C15 | −178.67 (14) | C5—C6—N2—C7 | −20.68 (14) |
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2···O1i | 0.82 | 2.02 | 2.7828 (15) | 155 |
C1—H1A···O2ii | 0.97 | 2.46 | 3.3040 (16) | 145 |
C57—H57B···O1 | 0.96 | 2.59 | 3.3859 (18) | 141 |
N2—H2A···O2 | 0.92 (2) | 2.27 (2) | 2.8016 (18) | 117 (2) |
Symmetry codes: (i) x, y−1, z; (ii) −x, y+1/2, −z+1/2. |
Experimental details
Crystal data | |
Chemical formula | C40H34N2O2 |
Mr | 574.69 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 293 |
a, b, c (Å) | 14.0679 (2), 7.7245 (1), 26.9686 (3) |
β (°) | 92.596 (1) |
V (Å3) | 2927.60 (7) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.08 |
Crystal size (mm) | 0.21 × 0.15 × 0.13 |
Data collection | |
Diffractometer | Bruker Kappa APEXII diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.973, 0.978 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 33520, 8777, 6575 |
Rint | 0.047 |
(sin θ/λ)max (Å−1) | 0.711 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.054, 0.137, 1.02 |
No. of reflections | 8777 |
No. of parameters | 404 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.48, −0.27 |
Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2···O1i | 0.82 | 2.02 | 2.7828 (15) | 155 |
C1—H1A···O2ii | 0.97 | 2.46 | 3.3040 (16) | 145 |
C57—H57B···O1 | 0.96 | 2.59 | 3.3859 (18) | 141 |
N2—H2A···O2 | 0.92 (2) | 2.27 (2) | 2.8016 (18) | 117 (2) |
Symmetry codes: (i) x, y−1, z; (ii) −x, y+1/2, −z+1/2. |
Acknowledgements
This project was supported by the Research Center, College of Science, King Saud University.
References
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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.
The pyrrolidine ring system has been the subject of research for more than three decades. Many natural and synthetic compounds with pyrrolidine moieties have received much attention because of their remarkable biological properties (Shorvon, 2001; Watson et al., 2001; Asano et al., 2000; Winchester et al., 1992). Recognizing the importance of such compounds in drug discovery and as a part of our ongoing research in the construction of novel heterocycles, has prompted us to investigate the 1,3-dipolar cycloaddition of bisarylmethylidene pyridinones with azomethine ylide generated in situ from acenaphthenequinone and proline, we and report the crystal structure of the resulting pyrrolidine cyclo-adduct in this paper.
In the title compound,C40H34N2 O2, the piperidine ring (N1/C1—C4/C9) adopts a half-chair conformation [Q = 0.6188 (2) Å, θ = 142.52 (2)°, ϕ = 123.6 (2)°; Cremer & Pople, 1975] which is in close agreement with those of the other related structures (Kumar et al. 2010; Kumar et al.2011; Kumar et al. 2012). The two fused pyrrolidine rings with atom sequences (N1/C4/C7—C9) and (N2/C4—C7), adopt a twisted envelope conformation (C9 atom as the flap) and an envelope conformation (C5 atom as the flap) respectively. The puckering parameters are Q = 0.4648 (15) Å, ϕ =325.20 (19)° for the N1/C4/C7—C9) pyrrolidine ring and Q = 0.3918 (16) Å, ϕ = 77.9 (2)° for the (N2/C4—C7) pyrrolidine ring. In the structure, the aryl ring C22—C27 is not coplanar with the mean plane of the piperidone ring [torsion angle C1—C2—C21—C22 is 5.77 (3)] °, which is due to non-bonded interactions between one of the ortho H atoms in the aryl ring and the equatorial H atom at the 2-position of the piperidone ring (H12A/H1A or H1B).
The molecular structure features weak intra-molecular N—H···O and C—H···O interactions. Intermolecular O2—H2···O1 bonds form an infinite one-dimensional chain parallel to the b axis, in a C11(7) motif (Bernstein et al., 1995).