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

In the title compound, C(26)H(18)N(2)O(3), the maximum deviations from planarity for the tetra-hydro-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 R(2) (2)(8) loops and C-H⋯O inter-actions 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 = 406.42

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.064

wR(F 2) = 0.178

S = 1.02

5742 reflections

288 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.45 e Å−3

Δρmin = −0.27 e Å−3

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 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812036227/hb6939sup1.cif

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

Supplementary material file. DOI: 10.1107/S1600536812036227/hb6939Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

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

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

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) ; (ii) .