2-(4-Methyl-phen-yl)-3-oxo-4-phenyl-2,3,3a,4,9,9a-hexa-hydro-1H-benzo[f]iso-indole-6-carbo-nitrile.

In the title compound, C26H22N2O, one phenyl ring, one five-membered N-heterocyclic ring and one six-membered carbocyclic ring make up the hexa-hydro-benzo[f]iso-indole core. Another phenyl group is attached to the heterocyclic N atom as a substituent. The non-aromatic five- and six-membered rings both exhibit boat conformations. In the crystal, weak C-H⋯O and C-H⋯N inter-actions establish the observed three-dimensional structure. The crystal studied was refined as an inversion twin.

Related literature

For background to domino reactions, see Zhao et al. (2012 ▶) and for palladium-catalyzed domino reactions, see Hu et al. (2009 ▶, 2010 ▶). For the wide variety of active pharmaceutical ingredients, natural products and other complex organic mol­ecules economically accessible, see: Yu & Hu (2012 ▶); Wang & Hu (2011 ▶). For benzo[f]isoindol-1-one derivatives as effective inter­mediates, see: Rixson et al. (2012 ▶).

Experimental

Crystal data

C26H22N2O

M = 378.45

Orthorhombic,

a = 25.005 (6) Å

b = 5.5023 (14) Å

c = 14.790 (4) Å

V = 2034.9 (9) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 291 K

0.28 × 0.24 × 0.22 mm

Data collection

Bruker SMART APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.972, T max = 0.983

14617 measured reflections

4001 independent reflections

2187 reflections with I > 2σ(I)

R int = 0.068

Refinement

R[F 2 > 2σ(F 2)] = 0.052

wR(F 2) = 0.095

S = 1.03

4001 reflections

264 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.13 e Å−3

Δρmin = −0.15 e Å−3

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: XP in SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813008568/im2425sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813008568/im2425Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813008568/im2425Isup3.cml

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

C26H22N2O	Dx = 1.235 Mg m−3
Mr = 378.45	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pca21	Cell parameters from 2537 reflections
a = 25.005 (6) Å	θ = 2.1–25.4°
b = 5.5023 (14) Å	µ = 0.08 mm−1
c = 14.790 (4) Å	T = 291 K
V = 2034.9 (9) Å3	Block, colourless
Z = 4	0.28 × 0.24 × 0.22 mm
F(000) = 800

Bruker SMART APEX CCD diffractometer	4001 independent reflections
Radiation source: sealed tube	2187 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.068
phi and ω scans	θmax = 26.0°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −30→29
Tmin = 0.972, Tmax = 0.983	k = −6→6
14617 measured reflections	l = −18→18

Refinement on F2	1 restraint
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.052	H-atom parameters constrained
wR(F2) = 0.095	w = 1/[σ2(Fo2) + (0.030P)2] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max < 0.001
4001 reflections	Δρmax = 0.13 e Å−3
264 parameters	Δρmin = −0.15 e Å−3

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. Refined as a 2-component inversion twin.

	x	y	z	Uiso*/Ueq
C1	0.27416 (18)	−0.1214 (8)	0.8866 (4)	0.0920 (15)
H1A	0.2484	−0.0456	0.9255	0.138*
H1B	0.2899	−0.2577	0.9171	0.138*
H1C	0.2568	−0.1761	0.8323	0.138*
C2	0.31699 (18)	0.0587 (8)	0.8628 (3)	0.0682 (12)
C3	0.31038 (18)	0.2255 (8)	0.7939 (3)	0.0762 (13)
H3	0.2783	0.2264	0.7621	0.091*
C4	0.34912 (17)	0.3895 (8)	0.7706 (3)	0.0741 (13)
H4	0.3424	0.5008	0.7247	0.089*
C5	0.39807 (16)	0.3928 (7)	0.8141 (3)	0.0543 (10)
C6	0.40556 (18)	0.2282 (8)	0.8835 (3)	0.0690 (13)
H6	0.4375	0.2277	0.9157	0.083*
C7	0.36579 (18)	0.0645 (8)	0.9050 (3)	0.0751 (14)
H7	0.3724	−0.0479	0.9506	0.090*
C8	0.42905 (15)	0.7232 (7)	0.7095 (3)	0.0594 (11)
H8A	0.4059	0.8575	0.7261	0.071*
H8B	0.4135	0.6377	0.6585	0.071*
C9	0.48494 (15)	0.8106 (7)	0.6881 (2)	0.0525 (10)
H9	0.5021	0.6863	0.6506	0.063*
C10	0.51232 (13)	0.8093 (7)	0.7792 (3)	0.0515 (10)
H10	0.5022	0.9586	0.8110	0.062*
C11	0.48623 (16)	0.6001 (7)	0.8268 (3)	0.0566 (11)
C12	0.57264 (14)	0.8097 (7)	0.7688 (2)	0.0515 (10)
H12	0.5823	0.6549	0.7404	0.062*
C13	0.58818 (16)	1.0120 (7)	0.7015 (3)	0.0545 (10)
C14	0.55105 (16)	1.1225 (7)	0.6438 (3)	0.0523 (10)
C15	0.49270 (16)	1.0529 (7)	0.6417 (3)	0.0640 (11)
H15A	0.4806	1.0424	0.5795	0.077*
H15B	0.4717	1.1763	0.6722	0.077*
C16	0.60352 (16)	0.8242 (7)	0.8567 (3)	0.0520 (10)
C17	0.63873 (18)	0.6434 (8)	0.8796 (3)	0.0755 (14)
H17	0.6434	0.5123	0.8407	0.091*
C18	0.6674 (2)	0.6525 (11)	0.9596 (4)	0.0998 (18)
H18	0.6907	0.5270	0.9747	0.120*
C19	0.6615 (2)	0.8440 (12)	1.0156 (4)	0.0884 (16)
H19	0.6810	0.8514	1.0690	0.106*
C20	0.62664 (19)	1.0285 (10)	0.9938 (3)	0.0782 (14)
H20	0.6226	1.1602	1.0326	0.094*
C21	0.59746 (17)	1.0182 (8)	0.9137 (3)	0.0625 (11)
H21	0.5739	1.1429	0.8989	0.075*
C22	0.64117 (16)	1.0829 (8)	0.6969 (3)	0.0624 (11)
H22	0.6661	1.0069	0.7341	0.075*
C23	0.65808 (19)	1.2639 (9)	0.6386 (3)	0.0681 (12)
C24	0.6207 (2)	1.3755 (8)	0.5835 (3)	0.0665 (12)
H24	0.6314	1.4998	0.5448	0.080*
C25	0.56853 (19)	1.3048 (7)	0.5855 (3)	0.0625 (12)
H25	0.5441	1.3796	0.5472	0.075*
C26	0.7132 (2)	1.3289 (10)	0.6345 (3)	0.0920 (17)
N1	0.43779 (13)	0.5579 (5)	0.7866 (2)	0.0536 (8)
N2	0.7571 (2)	1.3807 (9)	0.6321 (3)	0.1284 (19)
O1	0.50390 (11)	0.4871 (5)	0.8918 (2)	0.0770 (8)

	U11	U22	U33	U12	U13	U23
C1	0.078 (3)	0.098 (4)	0.101 (4)	−0.015 (3)	0.014 (3)	0.018 (4)
C2	0.070 (3)	0.066 (3)	0.069 (3)	−0.002 (2)	0.008 (3)	0.006 (3)
C3	0.058 (3)	0.088 (3)	0.083 (3)	−0.009 (3)	−0.010 (3)	0.022 (3)
C4	0.056 (3)	0.079 (3)	0.087 (3)	−0.005 (3)	−0.012 (3)	0.027 (3)
C5	0.055 (3)	0.055 (3)	0.053 (2)	0.005 (2)	0.000 (2)	0.004 (2)
C6	0.066 (3)	0.079 (3)	0.062 (3)	−0.001 (3)	−0.004 (2)	0.016 (3)
C7	0.079 (3)	0.083 (4)	0.063 (3)	−0.007 (3)	−0.003 (3)	0.022 (3)
C8	0.057 (3)	0.063 (3)	0.058 (3)	−0.001 (2)	−0.009 (2)	0.014 (2)
C9	0.055 (3)	0.056 (2)	0.046 (2)	0.003 (2)	−0.003 (2)	0.003 (2)
C10	0.050 (2)	0.052 (2)	0.052 (3)	0.005 (2)	−0.002 (2)	0.000 (2)
C11	0.054 (3)	0.060 (3)	0.055 (3)	0.009 (2)	0.002 (2)	0.003 (2)
C12	0.054 (2)	0.052 (2)	0.048 (2)	0.003 (2)	−0.002 (2)	−0.006 (2)
C13	0.060 (3)	0.061 (3)	0.042 (2)	0.002 (2)	0.004 (2)	−0.010 (2)
C14	0.060 (3)	0.050 (2)	0.046 (2)	0.002 (2)	0.002 (2)	−0.001 (2)
C15	0.070 (3)	0.067 (3)	0.055 (2)	0.004 (2)	−0.001 (2)	0.010 (2)
C16	0.053 (3)	0.051 (3)	0.052 (3)	−0.003 (2)	0.000 (2)	0.003 (2)
C17	0.081 (3)	0.062 (3)	0.083 (4)	0.010 (2)	−0.028 (3)	−0.003 (3)
C18	0.101 (4)	0.088 (4)	0.111 (5)	−0.005 (3)	−0.050 (4)	0.022 (4)
C19	0.091 (4)	0.112 (5)	0.063 (3)	−0.022 (4)	−0.018 (3)	0.018 (4)
C20	0.086 (4)	0.098 (4)	0.051 (3)	−0.017 (3)	0.009 (3)	−0.016 (3)
C21	0.067 (3)	0.074 (3)	0.047 (3)	0.000 (2)	0.004 (2)	−0.007 (2)
C22	0.059 (3)	0.082 (3)	0.046 (2)	−0.005 (2)	0.001 (2)	−0.007 (2)
C23	0.073 (3)	0.092 (3)	0.039 (2)	−0.023 (3)	0.011 (2)	−0.011 (3)
C24	0.092 (4)	0.066 (3)	0.042 (2)	−0.018 (3)	0.014 (3)	−0.008 (2)
C25	0.079 (3)	0.062 (3)	0.046 (3)	−0.004 (3)	0.008 (2)	−0.001 (2)
C26	0.094 (4)	0.140 (5)	0.042 (3)	−0.050 (4)	0.004 (3)	−0.001 (3)
N1	0.051 (2)	0.055 (2)	0.055 (2)	0.0007 (17)	−0.0069 (18)	0.0107 (17)
N2	0.110 (4)	0.214 (5)	0.061 (3)	−0.072 (4)	−0.001 (3)	0.005 (4)
O1	0.0645 (17)	0.096 (2)	0.0705 (19)	−0.0025 (16)	−0.0153 (17)	0.0313 (19)

C1—C2	1.501 (5)	C12—C13	1.543 (5)
C1—H1A	0.9600	C12—H12	0.9800
C1—H1B	0.9600	C13—C22	1.383 (5)
C1—H1C	0.9600	C13—C14	1.400 (5)
C2—C7	1.372 (5)	C14—C25	1.393 (5)
C2—C3	1.380 (6)	C14—C15	1.509 (5)
C3—C4	1.368 (6)	C15—H15A	0.9700
C3—H3	0.9300	C15—H15B	0.9700
C4—C5	1.383 (5)	C16—C21	1.369 (5)
C4—H4	0.9300	C16—C17	1.371 (5)
C5—C6	1.381 (5)	C17—C18	1.385 (6)
C5—N1	1.406 (5)	C17—H17	0.9300
C6—C7	1.379 (5)	C18—C19	1.348 (7)
C6—H6	0.9300	C18—H18	0.9300
C7—H7	0.9300	C19—C20	1.376 (6)
C8—N1	1.475 (5)	C19—H19	0.9300
C8—C9	1.512 (5)	C20—C21	1.393 (6)
C8—H8A	0.9700	C20—H20	0.9300
C8—H8B	0.9700	C21—H21	0.9300
C9—C15	1.512 (5)	C22—C23	1.384 (6)
C9—C10	1.512 (5)	C22—H22	0.9300
C9—H9	0.9800	C23—C24	1.383 (6)
C10—C11	1.499 (5)	C23—C26	1.424 (6)
C10—C12	1.516 (5)	C24—C25	1.363 (5)
C10—H10	0.9800	C24—H24	0.9300
C11—O1	1.227 (5)	C25—H25	0.9300
C11—N1	1.369 (5)	C26—N2	1.136 (6)
C12—C16	1.514 (5)
C2—C1—H1A	109.5	C10—C12—H12	106.8
C2—C1—H1B	109.5	C13—C12—H12	106.8
H1A—C1—H1B	109.5	C22—C13—C14	118.9 (4)
C2—C1—H1C	109.5	C22—C13—C12	118.4 (4)
H1A—C1—H1C	109.5	C14—C13—C12	122.6 (3)
H1B—C1—H1C	109.5	C25—C14—C13	118.8 (4)
C7—C2—C3	115.3 (4)	C25—C14—C15	118.3 (4)
C7—C2—C1	122.9 (4)	C13—C14—C15	122.9 (3)
C3—C2—C1	121.8 (4)	C14—C15—C9	109.8 (3)
C4—C3—C2	122.7 (4)	C14—C15—H15A	109.7
C4—C3—H3	118.7	C9—C15—H15A	109.7
C2—C3—H3	118.7	C14—C15—H15B	109.7
C3—C4—C5	121.2 (4)	C9—C15—H15B	109.7
C3—C4—H4	119.4	H15A—C15—H15B	108.2
C5—C4—H4	119.4	C21—C16—C17	119.0 (4)
C6—C5—C4	117.2 (4)	C21—C16—C12	120.9 (4)
C6—C5—N1	122.9 (4)	C17—C16—C12	120.1 (4)
C4—C5—N1	119.9 (4)	C16—C17—C18	121.2 (5)
C7—C6—C5	120.1 (4)	C16—C17—H17	119.4
C7—C6—H6	119.9	C18—C17—H17	119.4
C5—C6—H6	119.9	C19—C18—C17	119.7 (5)
C2—C7—C6	123.4 (4)	C19—C18—H18	120.2
C2—C7—H7	118.3	C17—C18—H18	120.2
C6—C7—H7	118.3	C18—C19—C20	120.2 (5)
N1—C8—C9	102.8 (3)	C18—C19—H19	119.9
N1—C8—H8A	111.2	C20—C19—H19	119.9
C9—C8—H8A	111.2	C19—C20—C21	120.0 (5)
N1—C8—H8B	111.2	C19—C20—H20	120.0
C9—C8—H8B	111.2	C21—C20—H20	120.0
H8A—C8—H8B	109.1	C16—C21—C20	119.9 (4)
C8—C9—C15	119.6 (3)	C16—C21—H21	120.1
C8—C9—C10	103.3 (3)	C20—C21—H21	120.1
C15—C9—C10	110.5 (3)	C13—C22—C23	121.7 (4)
C8—C9—H9	107.6	C13—C22—H22	119.1
C15—C9—H9	107.6	C23—C22—H22	119.1
C10—C9—H9	107.6	C24—C23—C22	118.7 (4)
C11—C10—C9	103.0 (3)	C24—C23—C26	121.1 (5)
C11—C10—C12	118.8 (3)	C22—C23—C26	120.2 (5)
C9—C10—C12	111.1 (3)	C25—C24—C23	120.4 (4)
C11—C10—H10	107.8	C25—C24—H24	119.8
C9—C10—H10	107.8	C23—C24—H24	119.8
C12—C10—H10	107.8	C24—C25—C14	121.3 (4)
O1—C11—N1	125.0 (4)	C24—C25—H25	119.3
O1—C11—C10	126.9 (4)	C14—C25—H25	119.3
N1—C11—C10	108.1 (3)	N2—C26—C23	179.3 (5)
C16—C12—C10	114.8 (3)	C11—N1—C5	127.5 (3)
C16—C12—C13	112.8 (3)	C11—N1—C8	111.3 (3)
C10—C12—C13	108.5 (3)	C5—N1—C8	121.2 (3)
C16—C12—H12	106.8
C7—C2—C3—C4	−1.5 (7)	C8—C9—C15—C14	169.1 (4)
C1—C2—C3—C4	−179.3 (5)	C10—C9—C15—C14	49.4 (4)
C2—C3—C4—C5	1.5 (7)	C10—C12—C16—C21	−60.2 (5)
C3—C4—C5—C6	−1.7 (6)	C13—C12—C16—C21	64.8 (4)
C3—C4—C5—N1	177.8 (4)	C10—C12—C16—C17	120.8 (4)
C4—C5—C6—C7	2.0 (6)	C13—C12—C16—C17	−114.2 (4)
N1—C5—C6—C7	−177.5 (4)	C21—C16—C17—C18	1.0 (7)
C3—C2—C7—C6	1.9 (7)	C12—C16—C17—C18	−180.0 (4)
C1—C2—C7—C6	179.6 (4)	C16—C17—C18—C19	−1.1 (8)
C5—C6—C7—C2	−2.2 (7)	C17—C18—C19—C20	0.7 (8)
N1—C8—C9—C15	−154.6 (3)	C18—C19—C20—C21	−0.1 (7)
N1—C8—C9—C10	−31.4 (4)	C17—C16—C21—C20	−0.4 (6)
C8—C9—C10—C11	32.8 (4)	C12—C16—C21—C20	−179.5 (4)
C15—C9—C10—C11	161.9 (3)	C19—C20—C21—C16	0.0 (6)
C8—C9—C10—C12	161.0 (3)	C14—C13—C22—C23	1.7 (6)
C15—C9—C10—C12	−69.8 (4)	C12—C13—C22—C23	−179.7 (4)
C9—C10—C11—O1	159.3 (4)	C13—C22—C23—C24	−0.1 (6)
C12—C10—C11—O1	36.0 (6)	C13—C22—C23—C26	−178.8 (4)
C9—C10—C11—N1	−22.2 (4)	C22—C23—C24—C25	−1.3 (6)
C12—C10—C11—N1	−145.5 (3)	C26—C23—C24—C25	177.3 (4)
C11—C10—C12—C16	−64.4 (5)	C23—C24—C25—C14	1.2 (6)
C9—C10—C12—C16	176.4 (3)	C13—C14—C25—C24	0.3 (6)
C11—C10—C12—C13	168.4 (3)	C15—C14—C25—C24	−179.6 (4)
C9—C10—C12—C13	49.2 (4)	O1—C11—N1—C5	4.4 (6)
C16—C12—C13—C22	37.2 (5)	C10—C11—N1—C5	−174.2 (3)
C10—C12—C13—C22	165.6 (3)	O1—C11—N1—C8	−179.2 (4)
C16—C12—C13—C14	−144.2 (4)	C10—C11—N1—C8	2.2 (4)
C10—C12—C13—C14	−15.8 (5)	C6—C5—N1—C11	−6.8 (6)
C22—C13—C14—C25	−1.7 (6)	C4—C5—N1—C11	173.8 (4)
C12—C13—C14—C25	179.7 (3)	C6—C5—N1—C8	177.2 (4)
C22—C13—C14—C15	178.2 (4)	C4—C5—N1—C8	−2.3 (5)
C12—C13—C14—C15	−0.4 (6)	C9—C8—N1—C11	18.7 (4)
C25—C14—C15—C9	163.7 (3)	C9—C8—N1—C5	−164.7 (3)
C13—C14—C15—C9	−16.2 (5)

D—H···A	D—H	H···A	D···A	D—H···A
C25—H25···O1i	0.93	2.69	3.577 (6)	159
C4—H4···N2ii	0.93	2.62	3.329 (6)	134
C21—H21···O1iii	0.93	2.58	3.498 (5)	169

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C25—H25⋯O1i	0.93	2.69	3.577 (6)	159
C4—H4⋯N2ii	0.93	2.62	3.329 (6)	134
C21—H21⋯O1iii	0.93	2.58	3.498 (5)	169

Symmetry codes: (i) ; (ii) ; (iii) .