(3′R)-3′-Benzyl-2′,3′-dihydro-1H-spiro­[indole-3,1′-naphtho­[2,3-c]pyrrole]-2,4′,9′-trione

Sharma, G.; Kumar, S.V.; Wahab, H.A.; Rosli, M.M.; Fun, H.-K.

doi:10.1107/S1600536812036227

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 68| Part 9| September 2012| Pages o2769-o2770

doi:10.1107/S1600536812036227

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(3′R)-3′-Benzyl-2′,3′-dihydro-1H-spiro[indole-3,1′-naphtho[2,3-c]pyrrole]-2,4′,9′-trione

Garima Sharma,^a,^b S. Vasanth Kumar,^a Habibah A. Wahab,^b,^c ‡ Mohd Mustaqim Rosli ^d and Hoong-Kun Fun ^d ^*§

^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

(Received 16 August 2012; accepted 19 August 2012; online 25 August 2012)

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

C₂₆H₁₈N₂O₃
M_r = 406.42
Monoclinic, P 2₁ /c
a = 10.2317 (4) Å
b = 26.2823 (8) Å
c = 7.8406 (3) Å
β = 109.122 (2)°
V = 1992.10 (12) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 100 K
0.36 × 0.20 × 0.10 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.968, T_max = 0.992
19577 measured reflections
5742 independent reflections
3338 reflections with I > 2σ(I)
R_int = 0.069

Refinement

R[F² > 2σ(F²)] = 0.064
wR(F²) = 0.178
S = 1.02
5742 reflections
288 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.45 e Å⁻³
Δρ_min = −0.27 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

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) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2009); cell refinement: 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

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812036227/hb6939sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812036227/hb6939Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812036227/hb6939Isup3.cml

checkCIF report

Comment top

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).

Related literature top

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 top

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.

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: 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).

Figures top

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.

(3'R)-3'-Benzyl-2',3'-dihydro-1H-spiro[indole-3,1'- naphtho[2,3-c]pyrrole]-2,4',9'-trione top

Crystal data top

C₂₆H₁₈N₂O₃	F(000) = 848
M_r = 406.42	D_x = 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

Data collection top

Bruker SMART APEXII CCD diffractometer	5742 independent reflections
Radiation source: fine-focus sealed tube	3338 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.069
ϕ and ω scans	θ_max = 30.0°, θ_min = 3.1°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −14→14
T_min = 0.968, T_max = 0.992	k = −36→36
19577 measured reflections	l = −10→10

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.064	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(F_o²) + (0.0823P)² + 0.2374P] where P = (F_o² + 2F_c²)/3
5742 reflections	(Δ/σ)_max < 0.001
288 parameters	Δρ_max = 0.45 e Å⁻³
0 restraints	Δρ_min = −0.27 e Å⁻³

Crystal data top

C₂₆H₁₈N₂O₃	V = 1992.10 (12) Å³
M_r = 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)°

Data collection top

Bruker SMART APEXII CCD diffractometer	5742 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	3338 reflections with I > 2σ(I)
T_min = 0.968, T_max = 0.992	R_int = 0.069
19577 measured reflections

Refinement top

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	Δρ_max = 0.45 e Å⁻³
5742 reflections	Δρ_min = −0.27 e Å⁻³
288 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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)*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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
M_r	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)
T_min, T_max	0.968, 0.992
No. of measured, independent and observed [I > 2σ(I)] reflections	19577, 5742, 3338
R_int	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
Δρ_max, Δρ_min (e Å⁻³)	0.45, −0.27

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

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.

Footnotes

‡Additional correspondence author, e-mail: habibahwahab@yahoo.co.uk.

§Thomson Reuters ResearcherID: A-3561-2009.

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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