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organic compounds
1-(2-Hydroxyethyl)-1′-methyl-4′-(naphthalen-1-yl)-1′′,2′′,3′′,4′′-tetrahydrodispiro[indoline-3,2′-pyrrolidine-3′,2′′-naphthalene]-2,1′′-dione
aDepartment of Physics, Kalasalingam University, Krishnankoil 626 126, India, bLaboratory of X-ray Crystallography, Indian Institute of Chemical Technology, Hyderabad 500 007, India, and cDepartment of Organic Chemistry, University of Madras, Guindy Campus, Chennai 600 025, India
*Correspondence e-mail: s_selvanayagam@rediffmail.com
In the title compound, C33H30N2O3, the pyrrolidine ring adopts an in which the H atom attached the an ortho-C atom deviates from the plane, whereas the cyclohexanone ring in the tetrahydronaphthalene fused-ring system adopts a sofa conformation. The oxindoline ring system is almost perpendicular with respect to the mean plane of the pyrrolidine ring, with a dihedral angle of 89.0 (1)°. Five intramolecular C—H⋯O close contacts are observed. In the crystal, molecules associate via O—H⋯O hydrogen bonds, forming R22(14) dimers. In addition, there are weak C—H⋯π interactions.
Related literature
For general background to pyrrolidine derivatives, see: Sundar et al. (2011); Crooks & Sommerville (1982
); Stylianakis et al. (2003
). For a related structure, see: Selvanayagam, Ravikumar et al. (2011
); Selvanayagam, Sridhar et al. (2011
). For ring-puckering parameters, see: Cremer & Pople (1975
); Nardelli (1983
).
Experimental
Crystal data
|
Data collection
|
Refinement
|
|
Data collection: SMART (Bruker, 2001); cell SAINT (Bruker, 2001
); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008
); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008
); molecular graphics: ORTEP-3 (Farrugia, 1997
) and PLATON (Spek, 2009
)'; software used to prepare material for publication: SHELXL97 and PLATON.
Supporting information
10.1107/S1600536812006617/bt5819sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536812006617/bt5819Isup2.hkl
To a mixture of 1-(2-hydroxyethyl)indoline-2,3-dione (1mmol), sarcosine (1mmol) and 2-naphthalidene-1,2,3,4-tetrahydronaphthalene-1-one (1mmol) was added and heated under reflux in methanol (20ml) until the disappearance of the starting materials as evidenced by TLC. The solvent was removed under vacuo and the crude product was subjected to
using petroleum ether-ethyl acetate Single crystals were grown by slow evaporation from methanol.H atoms were placed in idealized positions and allowed to ride on their parent atoms, with C—H distances of 0.93-0.98 Å and O—H distance of 0.82 Å, and Uiso(H) = 1.5Ueq(C) for methyl H and Uiso(H) = 1.2Ueq(C or O) for all other H atoms.
Data collection: SMART (Bruker, 2001); cell
SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2009)'; software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).C33H30N2O3 | F(000) = 1064 |
Mr = 502.59 | Dx = 1.301 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 18685 reflections |
a = 12.0236 (18) Å | θ = 2.2–27.8° |
b = 14.054 (2) Å | µ = 0.08 mm−1 |
c = 15.950 (2) Å | T = 292 K |
β = 107.796 (2)° | Block, colourless |
V = 2566.2 (7) Å3 | 0.22 × 0.20 × 0.18 mm |
Z = 4 |
Bruker SMART APEX CCD area-detector diffractometer | 4956 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.021 |
Graphite monochromator | θmax = 28.0°, θmin = 1.8° |
ω scans | h = −15→15 |
29561 measured reflections | k = −18→18 |
6100 independent reflections | l = −21→20 |
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)] = 0.044 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.130 | H-atom parameters constrained |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0763P)2 + 0.3393P] where P = (Fo2 + 2Fc2)/3 |
6100 reflections | (Δ/σ)max < 0.001 |
345 parameters | Δρmax = 0.27 e Å−3 |
0 restraints | Δρmin = −0.16 e Å−3 |
C33H30N2O3 | V = 2566.2 (7) Å3 |
Mr = 502.59 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 12.0236 (18) Å | µ = 0.08 mm−1 |
b = 14.054 (2) Å | T = 292 K |
c = 15.950 (2) Å | 0.22 × 0.20 × 0.18 mm |
β = 107.796 (2)° |
Bruker SMART APEX CCD area-detector diffractometer | 4956 reflections with I > 2σ(I) |
29561 measured reflections | Rint = 0.021 |
6100 independent reflections |
R[F2 > 2σ(F2)] = 0.044 | 0 restraints |
wR(F2) = 0.130 | H-atom parameters constrained |
S = 1.02 | Δρmax = 0.27 e Å−3 |
6100 reflections | Δρmin = −0.16 e Å−3 |
345 parameters |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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 | ||
N1 | 0.10384 (8) | 0.22419 (7) | 0.19534 (6) | 0.0402 (2) | |
N2 | 0.00850 (9) | −0.00310 (7) | 0.19134 (7) | 0.0459 (2) | |
O1 | 0.30700 (9) | 0.24467 (6) | 0.39617 (6) | 0.0558 (2) | |
O2 | 0.11658 (9) | 0.03889 (7) | 0.10210 (6) | 0.0555 (2) | |
O3 | −0.19054 (11) | 0.03227 (8) | 0.03809 (7) | 0.0652 (3) | |
H3 | −0.1606 | 0.0206 | −0.0006 | 0.098* | |
C1 | 0.19263 (10) | 0.24133 (9) | 0.15200 (8) | 0.0434 (3) | |
H1A | 0.1927 | 0.3073 | 0.1341 | 0.052* | |
H1B | 0.1812 | 0.2007 | 0.1009 | 0.052* | |
C2 | 0.30466 (10) | 0.21616 (8) | 0.22418 (7) | 0.0399 (2) | |
H2 | 0.3234 | 0.2710 | 0.2640 | 0.048* | |
C3 | 0.26925 (9) | 0.13307 (7) | 0.27700 (7) | 0.0365 (2) | |
C4 | 0.13143 (10) | 0.13071 (8) | 0.23768 (7) | 0.0369 (2) | |
C5 | −0.01552 (11) | 0.23600 (10) | 0.13839 (9) | 0.0523 (3) | |
H5A | −0.0279 | 0.3010 | 0.1194 | 0.078* | |
H5B | −0.0689 | 0.2195 | 0.1702 | 0.078* | |
H5C | −0.0286 | 0.1953 | 0.0880 | 0.078* | |
C6 | 0.41155 (11) | 0.19724 (9) | 0.19625 (8) | 0.0449 (3) | |
C7 | 0.40481 (14) | 0.14455 (11) | 0.12339 (10) | 0.0597 (4) | |
H7 | 0.3324 | 0.1218 | 0.0894 | 0.072* | |
C8 | 0.50454 (17) | 0.12346 (14) | 0.09794 (12) | 0.0758 (5) | |
H8 | 0.4970 | 0.0891 | 0.0467 | 0.091* | |
C9 | 0.61114 (15) | 0.15324 (14) | 0.14808 (13) | 0.0746 (5) | |
H9 | 0.6767 | 0.1379 | 0.1315 | 0.090* | |
C10 | 0.62429 (12) | 0.20652 (11) | 0.22432 (11) | 0.0603 (4) | |
C11 | 0.73543 (14) | 0.23652 (14) | 0.27924 (15) | 0.0771 (5) | |
H11 | 0.8019 | 0.2193 | 0.2646 | 0.093* | |
C12 | 0.74729 (15) | 0.28936 (15) | 0.35201 (15) | 0.0834 (6) | |
H12 | 0.8212 | 0.3078 | 0.3870 | 0.100* | |
C13 | 0.65024 (15) | 0.31585 (13) | 0.37427 (13) | 0.0769 (5) | |
H13 | 0.6588 | 0.3537 | 0.4237 | 0.092* | |
C14 | 0.54088 (13) | 0.28741 (10) | 0.32481 (10) | 0.0588 (4) | |
H14 | 0.4766 | 0.3055 | 0.3419 | 0.071* | |
C15 | 0.52372 (11) | 0.23149 (9) | 0.24881 (9) | 0.0480 (3) | |
C16 | 0.30264 (10) | 0.16184 (8) | 0.37488 (7) | 0.0397 (2) | |
C17 | 0.32705 (10) | 0.08631 (9) | 0.44286 (7) | 0.0412 (3) | |
C18 | 0.35333 (11) | 0.11383 (10) | 0.53084 (8) | 0.0496 (3) | |
H18 | 0.3584 | 0.1781 | 0.5453 | 0.060* | |
C19 | 0.37171 (13) | 0.04706 (12) | 0.59598 (9) | 0.0601 (4) | |
H19 | 0.3896 | 0.0658 | 0.6545 | 0.072* | |
C20 | 0.36361 (13) | −0.04786 (12) | 0.57435 (10) | 0.0643 (4) | |
H20 | 0.3742 | −0.0934 | 0.6184 | 0.077* | |
C21 | 0.34002 (13) | −0.07620 (10) | 0.48835 (10) | 0.0574 (3) | |
H21 | 0.3363 | −0.1407 | 0.4749 | 0.069* | |
C22 | 0.32156 (10) | −0.00945 (9) | 0.42105 (8) | 0.0445 (3) | |
C23 | 0.29843 (12) | −0.03946 (8) | 0.32751 (9) | 0.0494 (3) | |
H23A | 0.2166 | −0.0560 | 0.3029 | 0.059* | |
H23B | 0.3442 | −0.0958 | 0.3256 | 0.059* | |
C24 | 0.32839 (11) | 0.03774 (8) | 0.27179 (8) | 0.0433 (3) | |
H24A | 0.3053 | 0.0168 | 0.2109 | 0.052* | |
H24B | 0.4124 | 0.0469 | 0.2907 | 0.052* | |
C25 | 0.06134 (10) | 0.10957 (8) | 0.29967 (7) | 0.0388 (2) | |
C26 | 0.05570 (11) | 0.15438 (9) | 0.37485 (8) | 0.0462 (3) | |
H26 | 0.0992 | 0.2090 | 0.3950 | 0.055* | |
C27 | −0.01597 (13) | 0.11681 (11) | 0.42021 (9) | 0.0578 (4) | |
H27 | −0.0198 | 0.1463 | 0.4715 | 0.069* | |
C28 | −0.08122 (13) | 0.03680 (13) | 0.39040 (10) | 0.0634 (4) | |
H28 | −0.1276 | 0.0121 | 0.4224 | 0.076* | |
C29 | −0.07937 (12) | −0.00782 (11) | 0.31387 (9) | 0.0574 (3) | |
H29 | −0.1248 | −0.0614 | 0.2929 | 0.069* | |
C30 | −0.00761 (10) | 0.03006 (8) | 0.26956 (8) | 0.0435 (3) | |
C31 | 0.08823 (10) | 0.05013 (8) | 0.16833 (8) | 0.0420 (3) | |
C32 | −0.05995 (13) | −0.07827 (10) | 0.13719 (10) | 0.0569 (3) | |
H32A | −0.0609 | −0.1330 | 0.1740 | 0.068* | |
H32B | −0.0230 | −0.0974 | 0.0936 | 0.068* | |
C33 | −0.18359 (13) | −0.04818 (11) | 0.09099 (10) | 0.0604 (4) | |
H33A | −0.2245 | −0.1003 | 0.0547 | 0.072* | |
H33B | −0.2227 | −0.0349 | 0.1347 | 0.072* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0400 (5) | 0.0397 (5) | 0.0409 (5) | 0.0025 (4) | 0.0125 (4) | 0.0074 (4) |
N2 | 0.0489 (6) | 0.0408 (5) | 0.0435 (5) | −0.0068 (4) | 0.0073 (4) | −0.0023 (4) |
O1 | 0.0814 (7) | 0.0387 (5) | 0.0462 (5) | −0.0043 (4) | 0.0181 (5) | −0.0082 (4) |
O2 | 0.0625 (6) | 0.0640 (6) | 0.0414 (5) | −0.0040 (4) | 0.0178 (4) | −0.0132 (4) |
O3 | 0.0724 (7) | 0.0672 (6) | 0.0546 (6) | 0.0100 (5) | 0.0171 (5) | 0.0018 (5) |
C1 | 0.0446 (6) | 0.0444 (6) | 0.0425 (6) | 0.0008 (5) | 0.0152 (5) | 0.0075 (5) |
C2 | 0.0406 (6) | 0.0385 (6) | 0.0409 (6) | −0.0016 (4) | 0.0131 (5) | 0.0007 (4) |
C3 | 0.0405 (6) | 0.0340 (5) | 0.0346 (5) | 0.0005 (4) | 0.0106 (4) | −0.0017 (4) |
C4 | 0.0413 (6) | 0.0353 (5) | 0.0341 (5) | −0.0008 (4) | 0.0113 (4) | 0.0003 (4) |
C5 | 0.0432 (7) | 0.0575 (8) | 0.0532 (7) | 0.0032 (5) | 0.0103 (5) | 0.0145 (6) |
C6 | 0.0449 (6) | 0.0457 (6) | 0.0461 (6) | 0.0018 (5) | 0.0170 (5) | 0.0061 (5) |
C7 | 0.0603 (8) | 0.0694 (9) | 0.0528 (7) | 0.0048 (7) | 0.0223 (6) | −0.0030 (6) |
C8 | 0.0860 (12) | 0.0850 (12) | 0.0696 (10) | 0.0159 (9) | 0.0435 (9) | −0.0009 (9) |
C9 | 0.0644 (10) | 0.0850 (11) | 0.0888 (12) | 0.0199 (8) | 0.0447 (9) | 0.0227 (10) |
C10 | 0.0489 (7) | 0.0606 (8) | 0.0762 (10) | 0.0076 (6) | 0.0264 (7) | 0.0291 (7) |
C11 | 0.0430 (8) | 0.0840 (12) | 0.1049 (14) | 0.0056 (7) | 0.0236 (8) | 0.0441 (11) |
C12 | 0.0495 (9) | 0.0860 (13) | 0.1007 (15) | −0.0155 (8) | 0.0022 (9) | 0.0262 (11) |
C13 | 0.0629 (10) | 0.0701 (10) | 0.0830 (11) | −0.0189 (8) | 0.0007 (8) | 0.0044 (9) |
C14 | 0.0500 (7) | 0.0546 (8) | 0.0660 (9) | −0.0086 (6) | 0.0090 (6) | 0.0026 (6) |
C15 | 0.0430 (6) | 0.0447 (6) | 0.0568 (7) | 0.0013 (5) | 0.0159 (5) | 0.0167 (5) |
C16 | 0.0415 (6) | 0.0378 (6) | 0.0387 (5) | −0.0004 (4) | 0.0104 (4) | −0.0034 (4) |
C17 | 0.0386 (6) | 0.0454 (6) | 0.0377 (5) | 0.0024 (5) | 0.0088 (4) | 0.0012 (5) |
C18 | 0.0482 (7) | 0.0594 (8) | 0.0405 (6) | 0.0038 (6) | 0.0125 (5) | −0.0024 (5) |
C19 | 0.0564 (8) | 0.0838 (11) | 0.0390 (6) | 0.0105 (7) | 0.0133 (6) | 0.0085 (6) |
C20 | 0.0606 (9) | 0.0761 (10) | 0.0555 (8) | 0.0123 (7) | 0.0167 (7) | 0.0265 (7) |
C21 | 0.0583 (8) | 0.0502 (7) | 0.0614 (8) | 0.0060 (6) | 0.0149 (6) | 0.0141 (6) |
C22 | 0.0409 (6) | 0.0430 (6) | 0.0469 (6) | 0.0035 (5) | 0.0093 (5) | 0.0056 (5) |
C23 | 0.0580 (7) | 0.0339 (6) | 0.0504 (7) | 0.0049 (5) | 0.0080 (6) | −0.0015 (5) |
C24 | 0.0481 (6) | 0.0388 (6) | 0.0409 (6) | 0.0058 (5) | 0.0104 (5) | −0.0050 (4) |
C25 | 0.0412 (6) | 0.0378 (5) | 0.0373 (5) | 0.0030 (4) | 0.0119 (4) | 0.0058 (4) |
C26 | 0.0499 (7) | 0.0474 (6) | 0.0417 (6) | 0.0076 (5) | 0.0147 (5) | 0.0030 (5) |
C27 | 0.0603 (8) | 0.0749 (10) | 0.0432 (7) | 0.0141 (7) | 0.0234 (6) | 0.0107 (6) |
C28 | 0.0541 (8) | 0.0854 (11) | 0.0550 (8) | 0.0013 (7) | 0.0229 (6) | 0.0247 (7) |
C29 | 0.0529 (7) | 0.0608 (8) | 0.0564 (8) | −0.0097 (6) | 0.0134 (6) | 0.0168 (6) |
C30 | 0.0434 (6) | 0.0431 (6) | 0.0414 (6) | −0.0001 (5) | 0.0092 (5) | 0.0085 (5) |
C31 | 0.0429 (6) | 0.0414 (6) | 0.0386 (6) | −0.0001 (5) | 0.0079 (5) | −0.0026 (4) |
C32 | 0.0621 (8) | 0.0406 (7) | 0.0592 (8) | −0.0100 (6) | 0.0053 (6) | −0.0056 (6) |
C33 | 0.0583 (8) | 0.0640 (9) | 0.0517 (7) | −0.0152 (6) | 0.0063 (6) | −0.0021 (6) |
N1—C5 | 1.4545 (16) | C12—H12 | 0.9300 |
N1—C1 | 1.4582 (15) | C13—C14 | 1.370 (2) |
N1—C4 | 1.4681 (14) | C13—H13 | 0.9300 |
N2—C31 | 1.3522 (16) | C14—C15 | 1.406 (2) |
N2—C30 | 1.3996 (16) | C14—H14 | 0.9300 |
N2—C32 | 1.4508 (16) | C16—C17 | 1.4812 (16) |
O1—C16 | 1.2091 (14) | C17—C22 | 1.3865 (17) |
O2—C31 | 1.2154 (15) | C17—C18 | 1.3957 (16) |
O3—C33 | 1.3979 (18) | C18—C19 | 1.3669 (19) |
O3—H3 | 0.8200 | C18—H18 | 0.9300 |
C1—C2 | 1.5222 (16) | C19—C20 | 1.374 (2) |
C1—H1A | 0.9700 | C19—H19 | 0.9300 |
C1—H1B | 0.9700 | C20—C21 | 1.372 (2) |
C2—C6 | 1.5069 (17) | C20—H20 | 0.9300 |
C2—C3 | 1.5729 (15) | C21—C22 | 1.3914 (18) |
C2—H2 | 0.9800 | C21—H21 | 0.9300 |
C3—C24 | 1.5308 (15) | C22—C23 | 1.4926 (18) |
C3—C16 | 1.5423 (15) | C23—C24 | 1.5142 (18) |
C3—C4 | 1.5828 (16) | C23—H23A | 0.9700 |
C4—C25 | 1.5118 (15) | C23—H23B | 0.9700 |
C4—C31 | 1.5572 (15) | C24—H24A | 0.9700 |
C5—H5A | 0.9600 | C24—H24B | 0.9700 |
C5—H5B | 0.9600 | C25—C26 | 1.3743 (17) |
C5—H5C | 0.9600 | C25—C30 | 1.3868 (17) |
C6—C7 | 1.3593 (19) | C26—C27 | 1.3876 (19) |
C6—C15 | 1.4361 (18) | C26—H26 | 0.9300 |
C7—C8 | 1.410 (2) | C27—C28 | 1.370 (2) |
C7—H7 | 0.9300 | C27—H27 | 0.9300 |
C8—C9 | 1.353 (3) | C28—C29 | 1.378 (2) |
C8—H8 | 0.9300 | C28—H28 | 0.9300 |
C9—C10 | 1.395 (3) | C29—C30 | 1.3784 (18) |
C9—H9 | 0.9300 | C29—H29 | 0.9300 |
C10—C11 | 1.420 (2) | C32—C33 | 1.504 (2) |
C10—C15 | 1.4236 (19) | C32—H32A | 0.9700 |
C11—C12 | 1.348 (3) | C32—H32B | 0.9700 |
C11—H11 | 0.9300 | C33—H33A | 0.9700 |
C12—C13 | 1.371 (3) | C33—H33B | 0.9700 |
C5—N1—C1 | 114.25 (9) | O1—C16—C17 | 120.16 (10) |
C5—N1—C4 | 115.50 (9) | O1—C16—C3 | 120.81 (10) |
C1—N1—C4 | 105.70 (9) | C17—C16—C3 | 119.02 (9) |
C31—N2—C30 | 111.13 (10) | C22—C17—C18 | 120.00 (11) |
C31—N2—C32 | 124.16 (11) | C22—C17—C16 | 121.90 (10) |
C30—N2—C32 | 124.42 (11) | C18—C17—C16 | 118.09 (11) |
C33—O3—H3 | 109.5 | C19—C18—C17 | 120.55 (13) |
N1—C1—C2 | 102.12 (9) | C19—C18—H18 | 119.7 |
N1—C1—H1A | 111.3 | C17—C18—H18 | 119.7 |
C2—C1—H1A | 111.3 | C18—C19—C20 | 119.55 (13) |
N1—C1—H1B | 111.3 | C18—C19—H19 | 120.2 |
C2—C1—H1B | 111.3 | C20—C19—H19 | 120.2 |
H1A—C1—H1B | 109.2 | C21—C20—C19 | 120.66 (13) |
C6—C2—C1 | 117.06 (10) | C21—C20—H20 | 119.7 |
C6—C2—C3 | 114.98 (9) | C19—C20—H20 | 119.7 |
C1—C2—C3 | 104.82 (9) | C20—C21—C22 | 120.73 (14) |
C6—C2—H2 | 106.4 | C20—C21—H21 | 119.6 |
C1—C2—H2 | 106.4 | C22—C21—H21 | 119.6 |
C3—C2—H2 | 106.4 | C17—C22—C21 | 118.48 (12) |
C24—C3—C16 | 107.63 (9) | C17—C22—C23 | 120.34 (11) |
C24—C3—C2 | 114.47 (9) | C21—C22—C23 | 121.17 (12) |
C16—C3—C2 | 108.55 (9) | C22—C23—C24 | 112.28 (10) |
C24—C3—C4 | 114.06 (9) | C22—C23—H23A | 109.1 |
C16—C3—C4 | 108.89 (9) | C24—C23—H23A | 109.1 |
C2—C3—C4 | 103.02 (8) | C22—C23—H23B | 109.1 |
N1—C4—C25 | 112.58 (9) | C24—C23—H23B | 109.1 |
N1—C4—C31 | 110.16 (9) | H23A—C23—H23B | 107.9 |
C25—C4—C31 | 100.96 (9) | C23—C24—C3 | 113.42 (10) |
N1—C4—C3 | 103.03 (8) | C23—C24—H24A | 108.9 |
C25—C4—C3 | 118.06 (9) | C3—C24—H24A | 108.9 |
C31—C4—C3 | 112.22 (9) | C23—C24—H24B | 108.9 |
N1—C5—H5A | 109.5 | C3—C24—H24B | 108.9 |
N1—C5—H5B | 109.5 | H24A—C24—H24B | 107.7 |
H5A—C5—H5B | 109.5 | C26—C25—C30 | 119.19 (11) |
N1—C5—H5C | 109.5 | C26—C25—C4 | 131.81 (11) |
H5A—C5—H5C | 109.5 | C30—C25—C4 | 109.00 (10) |
H5B—C5—H5C | 109.5 | C25—C26—C27 | 118.99 (13) |
C7—C6—C15 | 118.79 (12) | C25—C26—H26 | 120.5 |
C7—C6—C2 | 121.02 (12) | C27—C26—H26 | 120.5 |
C15—C6—C2 | 120.13 (11) | C28—C27—C26 | 120.81 (13) |
C6—C7—C8 | 121.79 (15) | C28—C27—H27 | 119.6 |
C6—C7—H7 | 119.1 | C26—C27—H27 | 119.6 |
C8—C7—H7 | 119.1 | C27—C28—C29 | 121.20 (13) |
C9—C8—C7 | 120.01 (16) | C27—C28—H28 | 119.4 |
C9—C8—H8 | 120.0 | C29—C28—H28 | 119.4 |
C7—C8—H8 | 120.0 | C30—C29—C28 | 117.41 (13) |
C8—C9—C10 | 121.04 (14) | C30—C29—H29 | 121.3 |
C8—C9—H9 | 119.5 | C28—C29—H29 | 121.3 |
C10—C9—H9 | 119.5 | C29—C30—C25 | 122.36 (12) |
C9—C10—C11 | 122.12 (15) | C29—C30—N2 | 127.39 (12) |
C9—C10—C15 | 119.47 (14) | C25—C30—N2 | 110.25 (10) |
C11—C10—C15 | 118.41 (17) | O2—C31—N2 | 125.07 (11) |
C12—C11—C10 | 121.79 (16) | O2—C31—C4 | 126.21 (11) |
C12—C11—H11 | 119.1 | N2—C31—C4 | 108.64 (10) |
C10—C11—H11 | 119.1 | N2—C32—C33 | 112.50 (12) |
C11—C12—C13 | 119.87 (16) | N2—C32—H32A | 109.1 |
C11—C12—H12 | 120.1 | C33—C32—H32A | 109.1 |
C13—C12—H12 | 120.1 | N2—C32—H32B | 109.1 |
C12—C13—C14 | 120.98 (19) | C33—C32—H32B | 109.1 |
C12—C13—H13 | 119.5 | H32A—C32—H32B | 107.8 |
C14—C13—H13 | 119.5 | O3—C33—C32 | 113.01 (12) |
C13—C14—C15 | 121.44 (16) | O3—C33—H33A | 109.0 |
C13—C14—H14 | 119.3 | C32—C33—H33A | 109.0 |
C15—C14—H14 | 119.3 | O3—C33—H33B | 109.0 |
C14—C15—C10 | 117.47 (13) | C32—C33—H33B | 109.0 |
C14—C15—C6 | 123.69 (12) | H33A—C33—H33B | 107.8 |
C10—C15—C6 | 118.82 (13) | ||
C5—N1—C1—C2 | −175.59 (10) | O1—C16—C17—C22 | 179.21 (12) |
C4—N1—C1—C2 | −47.49 (11) | C3—C16—C17—C22 | 0.48 (16) |
N1—C1—C2—C6 | 162.32 (10) | O1—C16—C17—C18 | 0.81 (17) |
N1—C1—C2—C3 | 33.58 (11) | C3—C16—C17—C18 | −177.92 (10) |
C6—C2—C3—C24 | −14.77 (14) | C22—C17—C18—C19 | −1.21 (19) |
C1—C2—C3—C24 | 115.21 (10) | C16—C17—C18—C19 | 177.22 (12) |
C6—C2—C3—C16 | 105.48 (11) | C17—C18—C19—C20 | −0.3 (2) |
C1—C2—C3—C16 | −124.54 (10) | C18—C19—C20—C21 | 1.6 (2) |
C6—C2—C3—C4 | −139.17 (10) | C19—C20—C21—C22 | −1.3 (2) |
C1—C2—C3—C4 | −9.19 (11) | C18—C17—C22—C21 | 1.49 (18) |
C5—N1—C4—C25 | −63.23 (13) | C16—C17—C22—C21 | −176.88 (11) |
C1—N1—C4—C25 | 169.41 (9) | C18—C17—C22—C23 | −177.44 (11) |
C5—N1—C4—C31 | 48.61 (13) | C16—C17—C22—C23 | 4.19 (18) |
C1—N1—C4—C31 | −78.75 (11) | C20—C21—C22—C17 | −0.3 (2) |
C5—N1—C4—C3 | 168.51 (10) | C20—C21—C22—C23 | 178.64 (13) |
C1—N1—C4—C3 | 41.16 (10) | C17—C22—C23—C24 | 21.81 (17) |
C24—C3—C4—N1 | −142.90 (9) | C21—C22—C23—C24 | −157.09 (12) |
C16—C3—C4—N1 | 96.87 (10) | C22—C23—C24—C3 | −53.54 (14) |
C2—C3—C4—N1 | −18.23 (10) | C16—C3—C24—C23 | 55.80 (13) |
C24—C3—C4—C25 | 92.34 (12) | C2—C3—C24—C23 | 176.56 (10) |
C16—C3—C4—C25 | −27.88 (13) | C4—C3—C24—C23 | −65.12 (13) |
C2—C3—C4—C25 | −142.98 (9) | N1—C4—C25—C26 | −61.43 (16) |
C24—C3—C4—C31 | −24.43 (13) | C31—C4—C25—C26 | −178.86 (12) |
C16—C3—C4—C31 | −144.66 (9) | C3—C4—C25—C26 | 58.47 (16) |
C2—C3—C4—C31 | 100.24 (10) | N1—C4—C25—C30 | 117.98 (10) |
C1—C2—C6—C7 | −42.55 (17) | C31—C4—C25—C30 | 0.55 (11) |
C3—C2—C6—C7 | 81.16 (15) | C3—C4—C25—C30 | −122.12 (10) |
C1—C2—C6—C15 | 140.16 (12) | C30—C25—C26—C27 | 2.18 (17) |
C3—C2—C6—C15 | −96.14 (13) | C4—C25—C26—C27 | −178.46 (12) |
C15—C6—C7—C8 | −0.5 (2) | C25—C26—C27—C28 | −0.6 (2) |
C2—C6—C7—C8 | −177.84 (14) | C26—C27—C28—C29 | −1.2 (2) |
C6—C7—C8—C9 | 2.2 (3) | C27—C28—C29—C30 | 1.3 (2) |
C7—C8—C9—C10 | −1.3 (3) | C28—C29—C30—C25 | 0.3 (2) |
C8—C9—C10—C11 | 178.36 (16) | C28—C29—C30—N2 | 179.84 (13) |
C8—C9—C10—C15 | −1.2 (2) | C26—C25—C30—C29 | −2.08 (18) |
C9—C10—C11—C12 | 178.86 (16) | C4—C25—C30—C29 | 178.42 (11) |
C15—C10—C11—C12 | −1.6 (2) | C26—C25—C30—N2 | 178.34 (10) |
C10—C11—C12—C13 | −0.3 (3) | C4—C25—C30—N2 | −1.16 (13) |
C11—C12—C13—C14 | 1.7 (3) | C31—N2—C30—C29 | −178.19 (13) |
C12—C13—C14—C15 | −1.1 (3) | C32—N2—C30—C29 | 7.8 (2) |
C13—C14—C15—C10 | −0.9 (2) | C31—N2—C30—C25 | 1.36 (14) |
C13—C14—C15—C6 | 177.94 (14) | C32—N2—C30—C25 | −172.66 (11) |
C9—C10—C15—C14 | −178.30 (13) | C30—N2—C31—O2 | −177.80 (12) |
C11—C10—C15—C14 | 2.11 (19) | C32—N2—C31—O2 | −3.8 (2) |
C9—C10—C15—C6 | 2.82 (19) | C30—N2—C31—C4 | −0.96 (13) |
C11—C10—C15—C6 | −176.76 (12) | C32—N2—C31—C4 | 173.07 (11) |
C7—C6—C15—C14 | 179.24 (13) | N1—C4—C31—O2 | 57.84 (15) |
C2—C6—C15—C14 | −3.40 (18) | C25—C4—C31—O2 | 177.03 (12) |
C7—C6—C15—C10 | −1.96 (18) | C3—C4—C31—O2 | −56.34 (15) |
C2—C6—C15—C10 | 175.39 (11) | N1—C4—C31—N2 | −118.95 (10) |
C24—C3—C16—O1 | 151.83 (12) | C25—C4—C31—N2 | 0.25 (11) |
C2—C3—C16—O1 | 27.41 (15) | C3—C4—C31—N2 | 126.88 (10) |
C4—C3—C16—O1 | −84.06 (13) | C31—N2—C32—C33 | −103.09 (15) |
C24—C3—C16—C17 | −29.45 (13) | C30—N2—C32—C33 | 70.17 (16) |
C2—C3—C16—C17 | −153.87 (10) | N2—C32—C33—O3 | 57.18 (17) |
C4—C3—C16—C17 | 94.66 (11) |
Cg1 is the centroid of the C10–C15 phenyl ring. |
D—H···A | D—H | H···A | D···A | D—H···A |
C26—H26···O1 | 0.93 | 2.54 | 3.198 (2) | 128 |
C24—H24A···O2 | 0.97 | 2.42 | 3.098 (2) | 127 |
C14—H14···O1 | 0.93 | 2.59 | 3.394 (2) | 145 |
C2—H2···O1 | 0.98 | 2.21 | 2.764 (2) | 115 |
C1—H1B···O2 | 0.97 | 2.40 | 3.020 (2) | 121 |
O3—H3···O2i | 0.82 | 2.03 | 2.830 (1) | 164 |
C20—H20···Cg1ii | 0.93 | 2.71 | 3.603 (2) | 161 |
Symmetry codes: (i) −x, −y, −z; (ii) −x, −y, −z+1. |
Experimental details
Crystal data | |
Chemical formula | C33H30N2O3 |
Mr | 502.59 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 292 |
a, b, c (Å) | 12.0236 (18), 14.054 (2), 15.950 (2) |
β (°) | 107.796 (2) |
V (Å3) | 2566.2 (7) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.08 |
Crystal size (mm) | 0.22 × 0.20 × 0.18 |
Data collection | |
Diffractometer | Bruker SMART APEX CCD area-detector diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 29561, 6100, 4956 |
Rint | 0.021 |
(sin θ/λ)max (Å−1) | 0.660 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.044, 0.130, 1.02 |
No. of reflections | 6100 |
No. of parameters | 345 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.27, −0.16 |
Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2009)', SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).
Cg1 is the centroid of the C10–C15 phenyl ring. |
D—H···A | D—H | H···A | D···A | D—H···A |
C26—H26···O1 | 0.93 | 2.54 | 3.198 (2) | 128 |
C24—H24A···O2 | 0.97 | 2.42 | 3.098 (2) | 127 |
C14—H14···O1 | 0.93 | 2.59 | 3.394 (2) | 145 |
C2—H2···O1 | 0.98 | 2.21 | 2.764 (2) | 115 |
C1—H1B···O2 | 0.97 | 2.40 | 3.020 (2) | 121 |
O3—H3···O2i | 0.82 | 2.03 | 2.830 (1) | 164 |
C20—H20···Cg1ii | 0.93 | 2.71 | 3.603 (2) | 161 |
Symmetry codes: (i) −x, −y, −z; (ii) −x, −y, −z+1. |
Acknowledgements
SS acknowledges the Department of Science and Technology (DST), India, for providing computing facilities under the DST Fast Track Scheme. SS also thanks the Vice Chancellor and management of the Kalasalingam University, Krishnankoil, for their support and encouragement.
References
Bruker (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358. CrossRef CAS Web of Science Google Scholar
Crooks, P. A. & Sommerville, R. (1982). J. Pharm. Sci. 71, 291–294. CrossRef CAS PubMed Web of Science Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Nardelli, M. (1983). Acta Cryst. C39, 1141–1142. CrossRef CAS Web of Science IUCr Journals Google Scholar
Selvanayagam, S., Ravikumar, K., Saravanan, P. & Raghunathan, R. (2011). Acta Cryst. E67, o751. Web of Science CSD CrossRef IUCr Journals Google Scholar
Selvanayagam, S., Sridhar, B., Saravanan, P. & Raghunathan, R. (2011). Acta Cryst. E67, o1678–o1679. Web of Science CSD CrossRef CAS IUCr Journals 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
Stylianakis, I., Kolocouris, A., Kolocouris, N., Fytas, G., Foscolos, G. B., Padalko, E., Neyts, J. & De Clercq, E. (2003). Bioorg. Med. Chem. Lett. 13, 1699–1703. Web of Science CrossRef PubMed CAS Google Scholar
Sundar, J. K., Rajesh, S. M., Sivamani, J., Perumal, S. & Natarajan, S. (2011). Chem. Cent. J. 5, 45. Web of Science CSD CrossRef PubMed 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.
Spiro-pyrrolidine ring system is a structural motif in many biologically important and pharmacologically relevant alkaloids. These derivatives are used as antimicrobial and antitumour agents (Sundar et al., 2011). These derivatives possess analgesic (Crooks & Sommerville, 1982) and anti-influenza virus (Stylianakis et al., 2003) activities. In view of these importance and continuation of our work on the crystal structure analyis of spiro-pyrrolidine derivatives, we have undertaken the crystal structure determination of the title compound, and the results are presented here.
The X-ray study confirmed the molecular structure and atomic connectivity for (I), as illustrated in Fig. 1. The geometry of pyrrolidine, tetrahydro naphthalene and naphthyl group systems are comparable with the related reported structure (Selvanayagam, Ravikumar et al., 2011; Selvanayagam, Sridhar et al., 2011).
The sum of the angles at N1 of the pyrrolidine ring [335.5°] and N2 of the oxindole ring [359.7°] are in accordance with sp3 and sp2 hybridizations. The short contacts H1B···H7 (2.2 Å) and H2···H14 (1.9 Å) result in substantial widening of the C6—C7—C8 and C14—C15—C6 bond angles [121.8 (2)° and 123.7 (1)°, respectively].
Pyrrolidine ring adopts an envelope conformation, with puckering parameters q2 = 0.431 (1) Å and ϕ = 11.8 (1) °, and with atom C1 deviating 0.606 (1) Å from the least-squares plane passing through the remaining four atoms (N1/C2-C4) of that ring (Cremer & Pople, 1975). The cyclohexanone ring in the tetrahydro naphthaline ring system has a sofa conformation with the lowest asymmetry parameters of ΔC2(C3-C24) = 0.085 (1)° (Nardelli, 1983). The naphthalene ring system is oriented with a dihedral angles of 88.5 (1) and 41.8 (1)°, respectively with respect to the best plane of pyrrolidine ring and oxindole ring systems.
The molecular structure is influenced by an intramolecular C—H···O close contacts. Atom O1 acts as a trifurcated acceptor for three intramolecular C—H···O contacts. In the molecular packing, O—H···O hydrogen bonds involving atoms O3 and O2 link inversion-related molecules to form R22 (14) graph-set dimer (Fig. 2 and Table 1). In addition to this intermolecular C—H···π interactions are formed such that atom H20 is 2.71 Å from the centroid of the phenyl ring (C10-C15) at (-x,-y,1-z), with C20—H20··· centroid angle of 161° and C20···centroid distance of 3.603 (2) Å (Fig. 3).