organic compounds
(3′R)-3′-Benzyl-2′,3′-dihydro-1H-spiro[indole-3,1′-naphtho[2,3-c]pyrrole]-2,4′,9′-trione
aDepartment of Chemistry, Karunya University, Coimbatore, India, bSchool of Pharmaceutical Sciences, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, cMalaysian Institute of Pharmaceuticals and Nutraceuticals, Ministry of Science, Technology and Innovation, Halaman Bukit Gambir, 11700 Bayan Lepas, Penang, Malaysia, and dX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
*Correspondence e-mail: hkfun@usm.my
In the title compound, C26H18N2O3, the maximum deviations from planarity for the tetrahydro-1H-naphtho[2,3-c]pyrrole and indoline rings systems are 0.091 (1) and 0.012 (2) Å, respectively. These ring systems make a dihedral angle of 89.95 (6)° with each other and they make dihedral angles of 73.42 (8) and 71.28 (9)°, respectively, with the benzene ring. In the crystal, inversion dimers linked by pairs of N—H⋯O hydrogen bonds generate R22(8) loops and C—H⋯O interactions connect the dimers into corrugated sheets lying parallel to the bc plane.
Related literature
For a related structure, see: Sharma et al. (2012). For the biological activity of naphthoquinones, see: Babula et al. (2007). For 1,3-cycloaddition reactions involving naphthoquinones, see: Chen et al. (2011). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986).
Experimental
Crystal data
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Refinement
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Data collection: APEX2 (Bruker, 2009); cell SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009).
Supporting information
10.1107/S1600536812036227/hb6939sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536812036227/hb6939Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536812036227/hb6939Isup3.cml
A mixture of isatin (0.147 g, 1 mmol), L-phenylalanine (0.165 g, 1 mmol) and 1,4-naphthoquinone (0.158 g, 1 mmol) was refluxed in methanol (6 ml) until the starting material was completely utilized (monitored by thin layer chromatography). After leaving the resultant concoction to stand for 1 h, the reaction solid was washed with cool water (3 × 2.5 ml) and cool ethanol (3 × 0.5 ml). The crude reaction solid was re-crystallized from hot methanol to afford the pure product (80% yield) as yellow plates.
N bound H atom were located from a difference Fourier map and freely refined. The remaining H atoms were positioned geometrically and refined using a riding model with C—H = 0.95–1.00 Å and Uiso(H) = 1.2Ueq(C).
Data collection: APEX2 (Bruker, 2009); cell
SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).Fig. 1. The molecular structure of (I), showing 50% probability displacement ellipsoids. Fig. 2. The crystal packing of (I). Dashed lines indicate hydrogen bonds. H atoms not involved in the hydrogen bond interactions have been omitted for clarity. |
C26H18N2O3 | F(000) = 848 |
Mr = 406.42 | Dx = 1.355 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 2917 reflections |
a = 10.2317 (4) Å | θ = 3.6–30.0° |
b = 26.2823 (8) Å | µ = 0.09 mm−1 |
c = 7.8406 (3) Å | T = 100 K |
β = 109.122 (2)° | Plate, yellow |
V = 1992.10 (12) Å3 | 0.36 × 0.20 × 0.10 mm |
Z = 4 |
Bruker SMART APEXII CCD diffractometer | 5742 independent reflections |
Radiation source: fine-focus sealed tube | 3338 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.069 |
ϕ and ω scans | θmax = 30.0°, θmin = 3.1° |
Absorption correction: multi-scan (SADABS; Bruker, 2009) | h = −14→14 |
Tmin = 0.968, Tmax = 0.992 | k = −36→36 |
19577 measured reflections | l = −10→10 |
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)] = 0.064 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.178 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0823P)2 + 0.2374P] where P = (Fo2 + 2Fc2)/3 |
5742 reflections | (Δ/σ)max < 0.001 |
288 parameters | Δρmax = 0.45 e Å−3 |
0 restraints | Δρmin = −0.27 e Å−3 |
C26H18N2O3 | V = 1992.10 (12) Å3 |
Mr = 406.42 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 10.2317 (4) Å | µ = 0.09 mm−1 |
b = 26.2823 (8) Å | T = 100 K |
c = 7.8406 (3) Å | 0.36 × 0.20 × 0.10 mm |
β = 109.122 (2)° |
Bruker SMART APEXII CCD diffractometer | 5742 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2009) | 3338 reflections with I > 2σ(I) |
Tmin = 0.968, Tmax = 0.992 | Rint = 0.069 |
19577 measured reflections |
R[F2 > 2σ(F2)] = 0.064 | 0 restraints |
wR(F2) = 0.178 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.02 | Δρmax = 0.45 e Å−3 |
5742 reflections | Δρmin = −0.27 e Å−3 |
288 parameters |
Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K. |
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 | ||
O1 | 0.63086 (17) | 0.24596 (6) | −0.1639 (2) | 0.0425 (4) | |
O2 | 0.99431 (16) | 0.12903 (5) | 0.32957 (19) | 0.0322 (3) | |
O3 | 0.90923 (16) | 0.05795 (5) | −0.09244 (19) | 0.0303 (3) | |
N1 | 0.6184 (2) | 0.08098 (7) | −0.0952 (2) | 0.0323 (4) | |
N2 | 0.89813 (19) | 0.01158 (6) | 0.1530 (2) | 0.0279 (4) | |
C1 | 0.2987 (2) | 0.10602 (8) | −0.0342 (3) | 0.0326 (5) | |
H1A | 0.2716 | 0.0806 | −0.1253 | 0.039* | |
C2 | 0.2518 (2) | 0.10324 (8) | 0.1128 (3) | 0.0350 (5) | |
H2A | 0.1916 | 0.0765 | 0.1204 | 0.042* | |
C3 | 0.2923 (2) | 0.13924 (8) | 0.2481 (3) | 0.0334 (5) | |
H3A | 0.2610 | 0.1372 | 0.3494 | 0.040* | |
C4 | 0.3785 (2) | 0.17823 (8) | 0.2351 (3) | 0.0358 (5) | |
H4A | 0.4074 | 0.2030 | 0.3283 | 0.043* | |
C5 | 0.4237 (2) | 0.18162 (8) | 0.0863 (3) | 0.0322 (5) | |
H5A | 0.4818 | 0.2090 | 0.0778 | 0.039* | |
C6 | 0.3846 (2) | 0.14535 (7) | −0.0502 (3) | 0.0277 (4) | |
C7 | 0.4355 (2) | 0.14789 (8) | −0.2108 (3) | 0.0326 (5) | |
H7A | 0.4226 | 0.1830 | −0.2588 | 0.039* | |
H7B | 0.3772 | 0.1252 | −0.3065 | 0.039* | |
C8 | 0.5876 (2) | 0.13280 (8) | −0.1709 (3) | 0.0292 (5) | |
H8A | 0.6077 | 0.1336 | −0.2874 | 0.035* | |
C9 | 0.6946 (2) | 0.16499 (7) | −0.0368 (3) | 0.0259 (4) | |
C10 | 0.7108 (2) | 0.22060 (8) | −0.0448 (3) | 0.0301 (5) | |
C11 | 0.8288 (2) | 0.24382 (7) | 0.0988 (3) | 0.0299 (5) | |
C12 | 0.8434 (3) | 0.29669 (8) | 0.1069 (3) | 0.0393 (6) | |
H12A | 0.7767 | 0.3175 | 0.0231 | 0.047* | |
C13 | 0.9546 (3) | 0.31879 (9) | 0.2366 (4) | 0.0457 (7) | |
H13A | 0.9632 | 0.3548 | 0.2431 | 0.055* | |
C14 | 1.0541 (3) | 0.28861 (9) | 0.3576 (3) | 0.0432 (6) | |
H14A | 1.1317 | 0.3040 | 0.4442 | 0.052* | |
C15 | 1.0407 (2) | 0.23625 (8) | 0.3524 (3) | 0.0351 (5) | |
H15A | 1.1087 | 0.2158 | 0.4358 | 0.042* | |
C16 | 0.9273 (2) | 0.21352 (7) | 0.2246 (3) | 0.0284 (4) | |
C17 | 0.9102 (2) | 0.15717 (7) | 0.2248 (3) | 0.0250 (4) | |
C18 | 0.7843 (2) | 0.13671 (7) | 0.0901 (3) | 0.0243 (4) | |
C19 | 0.7453 (2) | 0.08120 (7) | 0.0663 (3) | 0.0247 (4) | |
C20 | 0.7310 (2) | 0.05476 (7) | 0.2298 (3) | 0.0286 (4) | |
C21 | 0.6447 (2) | 0.06580 (8) | 0.3289 (3) | 0.0351 (5) | |
H21A | 0.5821 | 0.0936 | 0.2975 | 0.042* | |
C22 | 0.6529 (3) | 0.03456 (9) | 0.4769 (3) | 0.0410 (6) | |
H22A | 0.5956 | 0.0412 | 0.5484 | 0.049* | |
C23 | 0.7448 (3) | −0.00613 (9) | 0.5190 (3) | 0.0410 (6) | |
H23A | 0.7485 | −0.0270 | 0.6194 | 0.049* | |
C24 | 0.8312 (3) | −0.01737 (8) | 0.4200 (3) | 0.0348 (5) | |
H24A | 0.8933 | −0.0454 | 0.4501 | 0.042* | |
C25 | 0.8228 (2) | 0.01413 (7) | 0.2749 (3) | 0.0276 (4) | |
C26 | 0.8609 (2) | 0.04958 (7) | 0.0286 (3) | 0.0248 (4) | |
H1N1 | 0.551 (3) | 0.0684 (11) | −0.059 (4) | 0.065 (9)* | |
H1N2 | 0.968 (3) | −0.0123 (9) | 0.156 (3) | 0.045 (7)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0417 (10) | 0.0389 (9) | 0.0539 (10) | 0.0140 (7) | 0.0252 (8) | 0.0197 (7) |
O2 | 0.0299 (9) | 0.0331 (8) | 0.0342 (8) | 0.0021 (6) | 0.0110 (7) | 0.0021 (6) |
O3 | 0.0354 (9) | 0.0290 (7) | 0.0322 (8) | 0.0062 (6) | 0.0188 (7) | 0.0033 (5) |
N1 | 0.0287 (10) | 0.0337 (10) | 0.0345 (10) | 0.0016 (8) | 0.0103 (8) | −0.0007 (7) |
N2 | 0.0326 (10) | 0.0244 (9) | 0.0290 (9) | 0.0045 (7) | 0.0135 (8) | 0.0022 (6) |
C1 | 0.0332 (13) | 0.0290 (11) | 0.0310 (11) | −0.0018 (9) | 0.0043 (9) | −0.0041 (8) |
C2 | 0.0327 (13) | 0.0322 (11) | 0.0382 (12) | −0.0071 (9) | 0.0092 (10) | 0.0050 (9) |
C3 | 0.0292 (12) | 0.0418 (12) | 0.0321 (11) | −0.0005 (9) | 0.0141 (9) | 0.0014 (9) |
C4 | 0.0338 (13) | 0.0426 (12) | 0.0345 (12) | −0.0083 (10) | 0.0161 (10) | −0.0112 (9) |
C5 | 0.0269 (12) | 0.0357 (11) | 0.0384 (12) | −0.0089 (9) | 0.0164 (10) | −0.0084 (9) |
C6 | 0.0214 (10) | 0.0328 (10) | 0.0275 (10) | 0.0036 (8) | 0.0058 (8) | −0.0008 (8) |
C7 | 0.0288 (12) | 0.0405 (12) | 0.0285 (11) | 0.0042 (9) | 0.0092 (9) | −0.0013 (8) |
C8 | 0.0302 (12) | 0.0353 (11) | 0.0253 (10) | 0.0051 (9) | 0.0133 (9) | 0.0022 (8) |
C9 | 0.0282 (11) | 0.0264 (10) | 0.0292 (10) | 0.0035 (8) | 0.0176 (8) | 0.0033 (7) |
C10 | 0.0316 (12) | 0.0301 (10) | 0.0373 (11) | 0.0073 (9) | 0.0233 (10) | 0.0089 (8) |
C11 | 0.0363 (12) | 0.0254 (10) | 0.0397 (12) | 0.0003 (8) | 0.0287 (10) | 0.0015 (8) |
C12 | 0.0479 (15) | 0.0277 (11) | 0.0605 (15) | 0.0024 (10) | 0.0424 (13) | 0.0036 (9) |
C13 | 0.0623 (18) | 0.0263 (11) | 0.0695 (17) | −0.0098 (11) | 0.0503 (15) | −0.0101 (11) |
C14 | 0.0493 (15) | 0.0423 (13) | 0.0521 (15) | −0.0191 (11) | 0.0358 (13) | −0.0163 (11) |
C15 | 0.0357 (13) | 0.0368 (12) | 0.0420 (12) | −0.0088 (9) | 0.0253 (10) | −0.0075 (9) |
C16 | 0.0314 (11) | 0.0270 (10) | 0.0362 (11) | −0.0033 (8) | 0.0240 (10) | −0.0035 (8) |
C17 | 0.0260 (11) | 0.0268 (10) | 0.0283 (10) | 0.0011 (8) | 0.0171 (8) | −0.0003 (7) |
C18 | 0.0261 (11) | 0.0253 (9) | 0.0268 (10) | 0.0016 (8) | 0.0161 (8) | 0.0001 (7) |
C19 | 0.0268 (11) | 0.0241 (9) | 0.0266 (10) | 0.0010 (8) | 0.0132 (8) | −0.0002 (7) |
C20 | 0.0344 (12) | 0.0281 (10) | 0.0266 (10) | −0.0029 (8) | 0.0143 (9) | −0.0004 (8) |
C21 | 0.0396 (14) | 0.0348 (11) | 0.0369 (12) | −0.0029 (10) | 0.0207 (10) | −0.0021 (9) |
C22 | 0.0489 (16) | 0.0439 (13) | 0.0389 (13) | −0.0104 (11) | 0.0262 (11) | −0.0029 (10) |
C23 | 0.0563 (17) | 0.0388 (12) | 0.0316 (12) | −0.0112 (11) | 0.0193 (11) | 0.0026 (9) |
C24 | 0.0453 (14) | 0.0282 (10) | 0.0295 (11) | −0.0045 (9) | 0.0103 (10) | 0.0025 (8) |
C25 | 0.0346 (12) | 0.0234 (9) | 0.0270 (10) | −0.0045 (8) | 0.0132 (9) | −0.0020 (7) |
C26 | 0.0266 (11) | 0.0235 (9) | 0.0254 (10) | 0.0007 (8) | 0.0101 (8) | −0.0015 (7) |
O1—C10 | 1.219 (2) | C9—C10 | 1.475 (3) |
O2—C17 | 1.225 (2) | C10—C11 | 1.485 (3) |
O3—C26 | 1.225 (2) | C11—C12 | 1.397 (3) |
N1—C8 | 1.478 (3) | C11—C16 | 1.404 (3) |
N1—C19 | 1.487 (3) | C12—C13 | 1.381 (4) |
N1—H1N1 | 0.89 (3) | C12—H12A | 0.9500 |
N2—C26 | 1.361 (2) | C13—C14 | 1.390 (4) |
N2—C25 | 1.413 (3) | C13—H13A | 0.9500 |
N2—H1N2 | 0.95 (3) | C14—C15 | 1.382 (3) |
C1—C2 | 1.388 (3) | C14—H14A | 0.9500 |
C1—C6 | 1.389 (3) | C15—C16 | 1.395 (3) |
C1—H1A | 0.9500 | C15—H15A | 0.9500 |
C2—C3 | 1.380 (3) | C16—C17 | 1.491 (3) |
C2—H2A | 0.9500 | C17—C18 | 1.474 (3) |
C3—C4 | 1.378 (3) | C18—C19 | 1.508 (3) |
C3—H3A | 0.9500 | C19—C20 | 1.507 (3) |
C4—C5 | 1.391 (3) | C19—C26 | 1.552 (3) |
C4—H4A | 0.9500 | C20—C21 | 1.384 (3) |
C5—C6 | 1.391 (3) | C20—C25 | 1.389 (3) |
C5—H5A | 0.9500 | C21—C22 | 1.402 (3) |
C6—C7 | 1.513 (3) | C21—H21A | 0.9500 |
C7—C8 | 1.536 (3) | C22—C23 | 1.390 (4) |
C7—H7A | 0.9900 | C22—H22A | 0.9500 |
C7—H7B | 0.9900 | C23—C24 | 1.387 (3) |
C8—C9 | 1.505 (3) | C23—H23A | 0.9500 |
C8—H8A | 1.0000 | C24—C25 | 1.386 (3) |
C9—C18 | 1.336 (3) | C24—H24A | 0.9500 |
C8—N1—C19 | 110.48 (16) | C11—C12—H12A | 119.9 |
C8—N1—H1N1 | 112.6 (19) | C12—C13—C14 | 120.3 (2) |
C19—N1—H1N1 | 106 (2) | C12—C13—H13A | 119.8 |
C26—N2—C25 | 111.33 (17) | C14—C13—H13A | 119.8 |
C26—N2—H1N2 | 122.5 (15) | C15—C14—C13 | 120.3 (2) |
C25—N2—H1N2 | 126.2 (15) | C15—C14—H14A | 119.8 |
C2—C1—C6 | 121.01 (19) | C13—C14—H14A | 119.8 |
C2—C1—H1A | 119.5 | C14—C15—C16 | 119.9 (2) |
C6—C1—H1A | 119.5 | C14—C15—H15A | 120.0 |
C3—C2—C1 | 120.3 (2) | C16—C15—H15A | 120.0 |
C3—C2—H2A | 119.9 | C15—C16—C11 | 119.91 (19) |
C1—C2—H2A | 119.9 | C15—C16—C17 | 119.7 (2) |
C4—C3—C2 | 119.5 (2) | C11—C16—C17 | 120.43 (19) |
C4—C3—H3A | 120.3 | O2—C17—C18 | 121.16 (17) |
C2—C3—H3A | 120.3 | O2—C17—C16 | 122.93 (19) |
C3—C4—C5 | 120.4 (2) | C18—C17—C16 | 115.90 (17) |
C3—C4—H4A | 119.8 | C9—C18—C17 | 123.79 (18) |
C5—C4—H4A | 119.8 | C9—C18—C19 | 110.90 (18) |
C6—C5—C4 | 120.7 (2) | C17—C18—C19 | 125.13 (17) |
C6—C5—H5A | 119.6 | N1—C19—C20 | 114.94 (17) |
C4—C5—H5A | 119.6 | N1—C19—C18 | 103.35 (15) |
C1—C6—C5 | 118.11 (19) | C20—C19—C18 | 115.91 (15) |
C1—C6—C7 | 120.54 (18) | N1—C19—C26 | 110.06 (15) |
C5—C6—C7 | 121.34 (19) | C20—C19—C26 | 101.98 (15) |
C6—C7—C8 | 114.88 (17) | C18—C19—C26 | 110.74 (16) |
C6—C7—H7A | 108.5 | C21—C20—C25 | 121.35 (19) |
C8—C7—H7A | 108.5 | C21—C20—C19 | 129.63 (19) |
C6—C7—H7B | 108.5 | C25—C20—C19 | 109.01 (17) |
C8—C7—H7B | 108.5 | C20—C21—C22 | 117.8 (2) |
H7A—C7—H7B | 107.5 | C20—C21—H21A | 121.1 |
N1—C8—C9 | 103.11 (16) | C22—C21—H21A | 121.1 |
N1—C8—C7 | 112.82 (18) | C23—C22—C21 | 119.9 (2) |
C9—C8—C7 | 116.98 (17) | C23—C22—H22A | 120.0 |
N1—C8—H8A | 107.8 | C21—C22—H22A | 120.0 |
C9—C8—H8A | 107.8 | C24—C23—C22 | 122.4 (2) |
C7—C8—H8A | 107.8 | C24—C23—H23A | 118.8 |
C18—C9—C10 | 121.58 (19) | C22—C23—H23A | 118.8 |
C18—C9—C8 | 111.86 (17) | C25—C24—C23 | 116.9 (2) |
C10—C9—C8 | 126.40 (18) | C25—C24—H24A | 121.6 |
O1—C10—C9 | 121.2 (2) | C23—C24—H24A | 121.6 |
O1—C10—C11 | 122.08 (19) | C24—C25—C20 | 121.6 (2) |
C9—C10—C11 | 116.72 (18) | C24—C25—N2 | 128.7 (2) |
C12—C11—C16 | 119.4 (2) | C20—C25—N2 | 109.71 (17) |
C12—C11—C10 | 119.4 (2) | O3—C26—N2 | 126.73 (19) |
C16—C11—C10 | 121.17 (18) | O3—C26—C19 | 125.32 (17) |
C13—C12—C11 | 120.1 (2) | N2—C26—C19 | 107.95 (16) |
C13—C12—H12A | 119.9 | ||
C6—C1—C2—C3 | −1.3 (3) | C10—C9—C18—C19 | −179.17 (16) |
C1—C2—C3—C4 | 0.7 (3) | C8—C9—C18—C19 | −3.6 (2) |
C2—C3—C4—C5 | 0.5 (3) | O2—C17—C18—C9 | −174.50 (18) |
C3—C4—C5—C6 | −1.1 (3) | C16—C17—C18—C9 | 5.6 (3) |
C2—C1—C6—C5 | 0.7 (3) | O2—C17—C18—C19 | 0.2 (3) |
C2—C1—C6—C7 | 179.80 (19) | C16—C17—C18—C19 | −179.66 (16) |
C4—C5—C6—C1 | 0.5 (3) | C8—N1—C19—C20 | 130.56 (17) |
C4—C5—C6—C7 | −178.6 (2) | C8—N1—C19—C18 | 3.3 (2) |
C1—C6—C7—C8 | −105.2 (2) | C8—N1—C19—C26 | −115.02 (17) |
C5—C6—C7—C8 | 73.9 (3) | C9—C18—C19—N1 | 0.2 (2) |
C19—N1—C8—C9 | −5.1 (2) | C17—C18—C19—N1 | −175.10 (17) |
C19—N1—C8—C7 | −132.25 (18) | C9—C18—C19—C20 | −126.48 (19) |
C6—C7—C8—N1 | 57.3 (2) | C17—C18—C19—C20 | 58.2 (2) |
C6—C7—C8—C9 | −62.1 (2) | C9—C18—C19—C26 | 118.02 (18) |
N1—C8—C9—C18 | 5.4 (2) | C17—C18—C19—C26 | −57.3 (2) |
C7—C8—C9—C18 | 129.81 (19) | N1—C19—C20—C21 | −61.8 (3) |
N1—C8—C9—C10 | −179.28 (18) | C18—C19—C20—C21 | 58.8 (3) |
C7—C8—C9—C10 | −54.8 (3) | C26—C19—C20—C21 | 179.2 (2) |
C18—C9—C10—O1 | 177.88 (19) | N1—C19—C20—C25 | 118.20 (19) |
C8—C9—C10—O1 | 3.0 (3) | C18—C19—C20—C25 | −121.20 (19) |
C18—C9—C10—C11 | −2.1 (3) | C26—C19—C20—C25 | −0.8 (2) |
C8—C9—C10—C11 | −177.06 (17) | C25—C20—C21—C22 | 0.0 (3) |
O1—C10—C11—C12 | 5.0 (3) | C19—C20—C21—C22 | −180.0 (2) |
C9—C10—C11—C12 | −174.99 (17) | C20—C21—C22—C23 | −0.5 (3) |
O1—C10—C11—C16 | −173.87 (18) | C21—C22—C23—C24 | 0.4 (4) |
C9—C10—C11—C16 | 6.1 (3) | C22—C23—C24—C25 | 0.2 (3) |
C16—C11—C12—C13 | 0.7 (3) | C23—C24—C25—C20 | −0.6 (3) |
C10—C11—C12—C13 | −178.23 (18) | C23—C24—C25—N2 | 179.8 (2) |
C11—C12—C13—C14 | 1.2 (3) | C21—C20—C25—C24 | 0.5 (3) |
C12—C13—C14—C15 | −1.7 (3) | C19—C20—C25—C24 | −179.47 (18) |
C13—C14—C15—C16 | 0.4 (3) | C21—C20—C25—N2 | −179.80 (19) |
C14—C15—C16—C11 | 1.5 (3) | C19—C20—C25—N2 | 0.2 (2) |
C14—C15—C16—C17 | −177.37 (18) | C26—N2—C25—C24 | −179.7 (2) |
C12—C11—C16—C15 | −2.0 (3) | C26—N2—C25—C20 | 0.7 (2) |
C10—C11—C16—C15 | 176.84 (18) | C25—N2—C26—O3 | 178.67 (19) |
C12—C11—C16—C17 | 176.85 (17) | C25—N2—C26—C19 | −1.2 (2) |
C10—C11—C16—C17 | −4.3 (3) | N1—C19—C26—O3 | 58.9 (3) |
C15—C16—C17—O2 | −2.4 (3) | C20—C19—C26—O3 | −178.64 (19) |
C11—C16—C17—O2 | 178.71 (18) | C18—C19—C26—O3 | −54.7 (3) |
C15—C16—C17—C18 | 177.45 (17) | N1—C19—C26—N2 | −121.22 (17) |
C11—C16—C17—C18 | −1.4 (2) | C20—C19—C26—N2 | 1.2 (2) |
C10—C9—C18—C17 | −3.8 (3) | C18—C19—C26—N2 | 125.13 (17) |
C8—C9—C18—C17 | 171.80 (17) |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H1N2···O3i | 0.95 (3) | 1.92 (3) | 2.840 (2) | 164 (2) |
C5—H5A···O1ii | 0.95 | 2.41 | 3.038 (3) | 123 |
Symmetry codes: (i) −x+2, −y, −z; (ii) x, −y+1/2, z+1/2. |
Experimental details
Crystal data | |
Chemical formula | C26H18N2O3 |
Mr | 406.42 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 100 |
a, b, c (Å) | 10.2317 (4), 26.2823 (8), 7.8406 (3) |
β (°) | 109.122 (2) |
V (Å3) | 1992.10 (12) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.36 × 0.20 × 0.10 |
Data collection | |
Diffractometer | Bruker SMART APEXII CCD diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 2009) |
Tmin, Tmax | 0.968, 0.992 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 19577, 5742, 3338 |
Rint | 0.069 |
(sin θ/λ)max (Å−1) | 0.703 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.064, 0.178, 1.02 |
No. of reflections | 5742 |
No. of parameters | 288 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.45, −0.27 |
Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H1N2···O3i | 0.95 (3) | 1.92 (3) | 2.840 (2) | 164 (2) |
C5—H5A···O1ii | 0.95 | 2.41 | 3.038 (3) | 123 |
Symmetry codes: (i) −x+2, −y, −z; (ii) x, −y+1/2, z+1/2. |
Acknowledgements
HAW gratefully acknowledges the Malaysian Ministry of Science, Technology and Innovation for the synthesis work funded by grants Nos. 09–05-lfn-meb-004 and 304/PFARMASI/650545/I121. GS and SVK thank the management and administration of Karunya University for their encouragement and support. HKF thanks USM for a Research University grant (No. 1001/PFIZIK/811160).
References
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Chen, H., Wang, S.-Y., Xu, X.-P. & Ji, S.-J. (2011). Synth. Commun. 41, 3280–3288. Web of Science CSD CrossRef CAS Google Scholar
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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.
This is a continuation of our recently published work (Sharma et al., 2012). Naphthoquinones are known to possess various biological properties (Babula et al., 2007). Recently, there also have been a few efforts to conduct 1, 3-cycloaddition involving naphthoquinones (Chen et al., 2011).
In the title compound, Fig. 1, all parameters are within normal ranges and comparable with the previously reported structure (Sharma et al., 2012). The tetrahydro-1H-naphtho[2,3-c]pyrrole (N1/C8—C19) and indoline (N2/C19—C26) rings are close to planar with the maximum deviations of 0.091 (2) Å for atom C8 and 0.012 (2) Å for atom C26. The two rings make a dihedral angle of 89.95 (6)° with each other and these two rings make dihedral angles of 73.42 (8)° and 71.28 (9)° with the benzene ring(C1—C6), respectively.
In the crystal, N2—H1N2···O3i and C5—H5A···O1ii (Table 1) connect the molecules into corrugated sheets parallel to the bc-plane (Fig. 2).