2,6-Bis[(S)-1-phenyl-eth-yl]-1H,5H-pyrrolo-[3,4-f]isoindole-1,3,5,7(2H,6H)-tetrone.

In the title compound, C(26)H(20)N(2)O(4), the central isoindole core is almost planar (r.m.s. deviation = 0.043 Å). The phenyl rings lie to either side of the plane [dihedral angles = 88.64 (5) and 67.74 (6)°] and the dihedral angle between the phenyl rings is 63.39 (7)°. In the crystal, mol-ecules are linked by C-H⋯O inter-actions; notably, one carbonyl O atom accepts three such bonds.

Related literature

For the biological activity of cyclic imides including that of the title compound, see: Abdel-Aziz (2007 ▶); Abdel-Aziz, El-Azab et al. (2011 ▶); Abdel-Aziz, ElTahir et al. (2011 ▶).

Experimental

Crystal data

C26H20N2O4

M = 424.44

Monoclinic,

a = 5.6401 (1) Å

b = 16.1040 (2) Å

c = 11.3759 (2) Å

β = 99.762 (2)°

V = 1018.29 (3) Å3

Z = 2

Cu Kα radiation

μ = 0.77 mm−1

T = 100 K

0.30 × 0.25 × 0.20 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ▶) T min = 0.656, T max = 1.000

7858 measured reflections

4093 independent reflections

4091 reflections with I > 2σ(I)

R int = 0.018

Refinement

R[F 2 > 2σ(F 2)] = 0.033

wR(F 2) = 0.099

S = 1.11

4093 reflections

289 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.24 e Å−3

Δρmin = −0.25 e Å−3

Absolute structure: Flack (1983 ▶), 1898 Friedel pairs

Flack parameter: 0.08 (12)

Data collection: CrysAlis PRO (Agilent, 2011 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO ; 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 DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812007684/bt5823sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812007684/bt5823Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812007684/bt5823Isup3.cml

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

C26H20N2O4	F(000) = 444
Mr = 424.44	Dx = 1.384 Mg m−3
Monoclinic, P21	Cu Kα radiation, λ = 1.5418 Å
Hall symbol: P 2yb	Cell parameters from 6911 reflections
a = 5.6401 (1) Å	θ = 2.7–76.5°
b = 16.1040 (2) Å	µ = 0.77 mm−1
c = 11.3759 (2) Å	T = 100 K
β = 99.762 (2)°	Prism, colourless
V = 1018.29 (3) Å3	0.30 × 0.25 × 0.20 mm
Z = 2

Agilent SuperNova Dual diffractometer with an Atlas detector	4093 independent reflections
Radiation source: SuperNova (Cu) X-ray Source	4091 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.018
Detector resolution: 10.4041 pixels mm-1	θmax = 76.7°, θmin = 3.9°
ω scan	h = −7→7
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	k = −20→20
Tmin = 0.656, Tmax = 1.000	l = −14→13
7858 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.033	H-atom parameters constrained
wR(F2) = 0.099	w = 1/[σ2(Fo2) + (0.0781P)2 + 0.0806P] where P = (Fo2 + 2Fc2)/3
S = 1.11	(Δ/σ)max < 0.001
4093 reflections	Δρmax = 0.24 e Å−3
289 parameters	Δρmin = −0.25 e Å−3
1 restraint	Absolute structure: Flack (1983), 1898 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.08 (12)

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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	−0.21322 (17)	0.49962 (6)	0.84958 (9)	0.0190 (2)
O2	0.52962 (18)	0.42601 (6)	1.05125 (9)	0.0204 (2)
O3	−0.18870 (17)	0.21623 (6)	0.51186 (8)	0.0194 (2)
O4	0.55058 (17)	0.13790 (6)	0.71548 (9)	0.0198 (2)
N1	0.1580 (2)	0.48014 (7)	0.97059 (10)	0.0157 (2)
N2	0.1824 (2)	0.15891 (7)	0.59322 (10)	0.0154 (2)
C1	0.1785 (2)	0.63194 (8)	0.97086 (11)	0.0156 (3)
C2	0.0123 (3)	0.69641 (9)	0.96693 (13)	0.0197 (3)
H2	−0.1151	0.6924	1.0116	0.024*
C3	0.0320 (3)	0.76653 (9)	0.89804 (14)	0.0224 (3)
H3	−0.0829	0.8099	0.8954	0.027*
C4	0.2184 (3)	0.77357 (9)	0.83304 (13)	0.0214 (3)
H4	0.2327	0.8219	0.7870	0.026*
C5	0.3837 (2)	0.70929 (10)	0.83595 (12)	0.0212 (3)
H5	0.5106	0.7133	0.7909	0.025*
C6	0.3636 (2)	0.63922 (9)	0.90455 (12)	0.0184 (3)
H6	0.4776	0.5956	0.9063	0.022*
C7	0.1695 (2)	0.55439 (8)	1.04732 (11)	0.0158 (3)
H7	0.3270	0.5517	1.1029	0.019*
C8	−0.0248 (3)	0.55292 (10)	1.12469 (13)	0.0211 (3)
H8A	−0.0150	0.5007	1.1696	0.032*
H8B	−0.1831	0.5573	1.0740	0.032*
H8C	−0.0017	0.5998	1.1804	0.032*
C9	−0.0287 (2)	0.46074 (8)	0.87821 (11)	0.0153 (3)
C10	0.0478 (2)	0.38325 (8)	0.82149 (12)	0.0146 (3)
C11	0.2743 (2)	0.36088 (8)	0.88183 (11)	0.0142 (3)
C12	0.3478 (2)	0.42320 (8)	0.97899 (12)	0.0150 (3)
C13	0.4002 (2)	0.29243 (8)	0.85060 (11)	0.0147 (3)
H13	0.5538	0.2767	0.8927	0.018*
C14	0.2814 (2)	0.24907 (8)	0.75224 (12)	0.0141 (2)
C15	0.0553 (2)	0.27140 (8)	0.69167 (11)	0.0144 (3)
C16	−0.0710 (2)	0.33948 (9)	0.72418 (12)	0.0151 (3)
H16	−0.2258	0.3547	0.6831	0.018*
C17	−0.0107 (2)	0.21467 (8)	0.58745 (12)	0.0150 (3)
C18	0.3646 (2)	0.17566 (8)	0.68996 (11)	0.0146 (2)
C19	0.2125 (2)	0.09707 (8)	0.50044 (12)	0.0158 (3)
H19	0.3719	0.0698	0.5268	0.019*
C20	0.2275 (3)	0.14171 (9)	0.38372 (12)	0.0201 (3)
H20A	0.3534	0.1843	0.3978	0.030*
H20B	0.0726	0.1680	0.3533	0.030*
H20C	0.2662	0.1016	0.3251	0.030*
C21	0.0229 (2)	0.02911 (8)	0.49308 (12)	0.0164 (3)
C22	−0.1846 (3)	0.02927 (9)	0.40638 (12)	0.0189 (3)
H22	−0.2102	0.0727	0.3491	0.023*
C23	−0.3546 (3)	−0.03401 (9)	0.40349 (13)	0.0207 (3)
H23	−0.4949	−0.0336	0.3440	0.025*
C24	−0.3199 (3)	−0.09748 (9)	0.48692 (14)	0.0218 (3)
H24	−0.4374	−0.1399	0.4857	0.026*
C25	−0.1120 (3)	−0.09870 (9)	0.57237 (14)	0.0249 (3)
H25	−0.0862	−0.1425	0.6291	0.030*
C26	0.0579 (3)	−0.03601 (10)	0.57488 (12)	0.0217 (3)
H26	0.2000	−0.0375	0.6332	0.026*

	U11	U22	U33	U12	U13	U23
O1	0.0176 (4)	0.0184 (5)	0.0201 (5)	0.0040 (4)	0.0006 (3)	−0.0031 (4)
O2	0.0200 (5)	0.0155 (5)	0.0229 (5)	−0.0003 (4)	−0.0038 (4)	−0.0023 (4)
O3	0.0173 (5)	0.0189 (5)	0.0201 (5)	0.0021 (4)	−0.0022 (4)	−0.0031 (4)
O4	0.0201 (5)	0.0184 (5)	0.0195 (4)	0.0061 (4)	−0.0005 (4)	−0.0008 (4)
N1	0.0179 (5)	0.0116 (6)	0.0170 (5)	0.0003 (4)	0.0013 (4)	−0.0026 (4)
N2	0.0164 (5)	0.0135 (5)	0.0156 (5)	0.0013 (4)	0.0009 (4)	−0.0017 (4)
C1	0.0153 (6)	0.0133 (6)	0.0173 (6)	−0.0007 (5)	−0.0001 (4)	−0.0050 (5)
C2	0.0197 (6)	0.0158 (7)	0.0245 (7)	0.0008 (5)	0.0064 (5)	−0.0033 (5)
C3	0.0242 (7)	0.0131 (6)	0.0280 (7)	0.0039 (5)	−0.0011 (6)	−0.0022 (5)
C4	0.0260 (7)	0.0161 (7)	0.0199 (6)	−0.0032 (5)	−0.0022 (5)	−0.0006 (5)
C5	0.0212 (7)	0.0234 (7)	0.0188 (6)	−0.0040 (6)	0.0032 (5)	−0.0036 (5)
C6	0.0162 (6)	0.0180 (7)	0.0207 (6)	0.0017 (5)	0.0023 (5)	−0.0042 (5)
C7	0.0182 (6)	0.0119 (6)	0.0168 (6)	−0.0008 (5)	0.0014 (4)	−0.0041 (5)
C8	0.0243 (7)	0.0191 (6)	0.0208 (6)	−0.0041 (5)	0.0060 (5)	−0.0033 (5)
C9	0.0183 (6)	0.0127 (6)	0.0146 (6)	−0.0019 (5)	0.0023 (5)	0.0004 (5)
C10	0.0161 (6)	0.0115 (6)	0.0163 (6)	0.0001 (5)	0.0030 (5)	0.0006 (5)
C11	0.0154 (6)	0.0125 (6)	0.0141 (6)	−0.0028 (5)	0.0012 (5)	0.0012 (5)
C12	0.0173 (6)	0.0108 (6)	0.0169 (6)	−0.0020 (5)	0.0024 (5)	0.0011 (5)
C13	0.0146 (6)	0.0136 (6)	0.0155 (6)	−0.0009 (5)	0.0015 (4)	0.0013 (5)
C14	0.0159 (6)	0.0112 (6)	0.0155 (5)	−0.0007 (5)	0.0030 (4)	0.0037 (5)
C15	0.0150 (6)	0.0129 (6)	0.0149 (6)	−0.0019 (5)	0.0014 (4)	0.0004 (4)
C16	0.0145 (6)	0.0133 (6)	0.0166 (6)	0.0009 (5)	0.0004 (4)	0.0011 (4)
C17	0.0163 (6)	0.0125 (6)	0.0160 (6)	−0.0002 (5)	0.0025 (4)	−0.0013 (5)
C18	0.0156 (6)	0.0143 (6)	0.0139 (6)	−0.0013 (5)	0.0028 (4)	0.0018 (5)
C19	0.0169 (6)	0.0144 (6)	0.0163 (6)	0.0015 (5)	0.0033 (4)	−0.0046 (5)
C20	0.0235 (6)	0.0193 (7)	0.0180 (6)	−0.0019 (5)	0.0045 (5)	−0.0021 (5)
C21	0.0196 (6)	0.0133 (6)	0.0162 (6)	0.0019 (5)	0.0027 (5)	−0.0035 (5)
C22	0.0204 (6)	0.0148 (6)	0.0205 (6)	0.0022 (5)	0.0007 (5)	0.0004 (5)
C23	0.0184 (6)	0.0190 (7)	0.0232 (7)	0.0014 (5)	−0.0011 (5)	−0.0039 (5)
C24	0.0239 (6)	0.0157 (7)	0.0260 (7)	−0.0019 (5)	0.0046 (5)	−0.0024 (5)
C25	0.0316 (7)	0.0196 (7)	0.0223 (7)	−0.0027 (6)	0.0012 (6)	0.0040 (5)
C26	0.0238 (7)	0.0203 (7)	0.0189 (6)	−0.0003 (6)	−0.0024 (5)	0.0005 (5)

O1—C9	1.2111 (17)	C10—C16	1.3855 (19)
O2—C12	1.2017 (16)	C10—C11	1.3915 (18)
O3—C17	1.2062 (16)	C11—C13	1.3897 (19)
O4—C18	1.2049 (16)	C11—C12	1.4984 (18)
N1—C9	1.3911 (16)	C13—C14	1.3909 (18)
N1—C12	1.4004 (17)	C13—H13	0.9500
N1—C7	1.4754 (16)	C14—C15	1.3902 (18)
N2—C18	1.3986 (16)	C14—C18	1.4941 (18)
N2—C17	1.4046 (16)	C15—C16	1.3913 (18)
N2—C19	1.4815 (16)	C15—C17	1.4930 (17)
C1—C6	1.3928 (18)	C16—H16	0.9500
C1—C2	1.3945 (18)	C19—C21	1.5222 (19)
C1—C7	1.5276 (18)	C19—C20	1.5249 (18)
C2—C3	1.390 (2)	C19—H19	1.0000
C2—H2	0.9500	C20—H20A	0.9800
C3—C4	1.389 (2)	C20—H20B	0.9800
C3—H3	0.9500	C20—H20C	0.9800
C4—C5	1.390 (2)	C21—C26	1.394 (2)
C4—H4	0.9500	C21—C22	1.3970 (18)
C5—C6	1.388 (2)	C22—C23	1.396 (2)
C5—H5	0.9500	C22—H22	0.9500
C6—H6	0.9500	C23—C24	1.386 (2)
C7—C8	1.5175 (18)	C23—H23	0.9500
C7—H7	1.0000	C24—C25	1.391 (2)
C8—H8A	0.9800	C24—H24	0.9500
C8—H8B	0.9800	C25—C26	1.389 (2)
C8—H8C	0.9800	C25—H25	0.9500
C9—C10	1.5012 (18)	C26—H26	0.9500
C9—N1—C12	112.10 (11)	C11—C13—C14	113.97 (11)
C9—N1—C7	125.51 (11)	C11—C13—H13	123.0
C12—N1—C7	122.27 (11)	C14—C13—H13	123.0
C18—N2—C17	111.95 (11)	C15—C14—C13	123.06 (12)
C18—N2—C19	122.19 (11)	C15—C14—C18	107.76 (11)
C17—N2—C19	125.31 (11)	C13—C14—C18	129.16 (12)
C6—C1—C2	118.78 (13)	C14—C15—C16	122.69 (12)
C6—C1—C7	118.53 (11)	C14—C15—C17	108.64 (11)
C2—C1—C7	122.67 (12)	C16—C15—C17	128.56 (12)
C3—C2—C1	120.37 (13)	C10—C16—C15	114.41 (11)
C3—C2—H2	119.8	C10—C16—H16	122.8
C1—C2—H2	119.8	C15—C16—H16	122.8
C4—C3—C2	120.44 (13)	O3—C17—N2	126.28 (12)
C4—C3—H3	119.8	O3—C17—C15	128.21 (12)
C2—C3—H3	119.8	N2—C17—C15	105.50 (10)
C3—C4—C5	119.48 (13)	O4—C18—N2	125.85 (13)
C3—C4—H4	120.3	O4—C18—C14	128.01 (12)
C5—C4—H4	120.3	N2—C18—C14	106.14 (11)
C6—C5—C4	120.03 (13)	N2—C19—C21	111.00 (10)
C6—C5—H5	120.0	N2—C19—C20	109.47 (11)
C4—C5—H5	120.0	C21—C19—C20	115.67 (11)
C5—C6—C1	120.89 (13)	N2—C19—H19	106.7
C5—C6—H6	119.6	C21—C19—H19	106.7
C1—C6—H6	119.6	C20—C19—H19	106.7
N1—C7—C8	111.52 (11)	C19—C20—H20A	109.5
N1—C7—C1	109.15 (10)	C19—C20—H20B	109.5
C8—C7—C1	116.11 (11)	H20A—C20—H20B	109.5
N1—C7—H7	106.5	C19—C20—H20C	109.5
C8—C7—H7	106.5	H20A—C20—H20C	109.5
C1—C7—H7	106.5	H20B—C20—H20C	109.5
C7—C8—H8A	109.5	C26—C21—C22	118.67 (13)
C7—C8—H8B	109.5	C26—C21—C19	119.05 (12)
H8A—C8—H8B	109.5	C22—C21—C19	122.29 (12)
C7—C8—H8C	109.5	C23—C22—C21	120.35 (13)
H8A—C8—H8C	109.5	C23—C22—H22	119.8
H8B—C8—H8C	109.5	C21—C22—H22	119.8
O1—C9—N1	126.36 (13)	C24—C23—C22	120.37 (12)
O1—C9—C10	127.63 (12)	C24—C23—H23	119.8
N1—C9—C10	106.01 (11)	C22—C23—H23	119.8
C16—C10—C11	122.80 (12)	C23—C24—C25	119.57 (13)
C16—C10—C9	129.12 (12)	C23—C24—H24	120.2
C11—C10—C9	108.05 (11)	C25—C24—H24	120.2
C13—C11—C10	123.07 (12)	C26—C25—C24	120.09 (13)
C13—C11—C12	129.09 (12)	C26—C25—H25	120.0
C10—C11—C12	107.84 (11)	C24—C25—H25	120.0
O2—C12—N1	125.16 (13)	C25—C26—C21	120.93 (13)
O2—C12—C11	128.83 (13)	C25—C26—H26	119.5
N1—C12—C11	106.01 (10)	C21—C26—H26	119.5
C6—C1—C2—C3	−0.06 (19)	C13—C14—C15—C16	0.31 (19)
C7—C1—C2—C3	178.47 (13)	C18—C14—C15—C16	−177.85 (11)
C1—C2—C3—C4	−0.5 (2)	C13—C14—C15—C17	176.77 (11)
C2—C3—C4—C5	0.9 (2)	C18—C14—C15—C17	−1.39 (14)
C3—C4—C5—C6	−0.8 (2)	C11—C10—C16—C15	−0.13 (18)
C4—C5—C6—C1	0.2 (2)	C9—C10—C16—C15	177.67 (12)
C2—C1—C6—C5	0.21 (19)	C14—C15—C16—C10	0.26 (18)
C7—C1—C6—C5	−178.38 (12)	C17—C15—C16—C10	−175.45 (12)
C9—N1—C7—C8	66.11 (16)	C18—N2—C17—O3	177.94 (13)
C12—N1—C7—C8	−118.32 (13)	C19—N2—C17—O3	6.4 (2)
C9—N1—C7—C1	−63.51 (15)	C18—N2—C17—C15	−0.74 (14)
C12—N1—C7—C1	112.06 (13)	C19—N2—C17—C15	−172.31 (12)
C6—C1—C7—N1	−57.40 (14)	C14—C15—C17—O3	−177.32 (13)
C2—C1—C7—N1	124.07 (13)	C16—C15—C17—O3	−1.1 (2)
C6—C1—C7—C8	175.54 (12)	C14—C15—C17—N2	1.33 (13)
C2—C1—C7—C8	−2.99 (18)	C16—C15—C17—N2	177.52 (12)
C12—N1—C9—O1	−179.01 (13)	C17—N2—C18—O4	−179.55 (12)
C7—N1—C9—O1	−3.1 (2)	C19—N2—C18—O4	−7.7 (2)
C12—N1—C9—C10	0.25 (14)	C17—N2—C18—C14	−0.08 (14)
C7—N1—C9—C10	176.20 (11)	C19—N2—C18—C14	171.80 (11)
O1—C9—C10—C16	0.9 (2)	C15—C14—C18—O4	−179.61 (13)
N1—C9—C10—C16	−178.40 (13)	C13—C14—C18—O4	2.4 (2)
O1—C9—C10—C11	178.91 (13)	C15—C14—C18—N2	0.93 (14)
N1—C9—C10—C11	−0.33 (13)	C13—C14—C18—N2	−177.07 (12)
C16—C10—C11—C13	−0.58 (19)	C18—N2—C19—C21	120.96 (13)
C9—C10—C11—C13	−178.79 (12)	C17—N2—C19—C21	−68.29 (16)
C16—C10—C11—C12	178.50 (12)	C18—N2—C19—C20	−110.14 (13)
C9—C10—C11—C12	0.29 (13)	C17—N2—C19—C20	60.61 (16)
C9—N1—C12—O2	−179.90 (13)	N2—C19—C21—C26	−81.30 (15)
C7—N1—C12—O2	4.0 (2)	C20—C19—C21—C26	153.20 (13)
C9—N1—C12—C11	−0.07 (14)	N2—C19—C21—C22	99.25 (14)
C7—N1—C12—C11	−176.18 (11)	C20—C19—C21—C22	−26.25 (18)
C13—C11—C12—O2	−1.3 (2)	C26—C21—C22—C23	1.0 (2)
C10—C11—C12—O2	179.68 (13)	C19—C21—C22—C23	−179.51 (12)
C13—C11—C12—N1	178.86 (12)	C21—C22—C23—C24	0.3 (2)
C10—C11—C12—N1	−0.15 (13)	C22—C23—C24—C25	−1.2 (2)
C10—C11—C13—C14	1.07 (18)	C23—C24—C25—C26	0.9 (2)
C12—C11—C13—C14	−177.80 (12)	C24—C25—C26—C21	0.5 (2)
C11—C13—C14—C15	−0.94 (18)	C22—C21—C26—C25	−1.4 (2)
C11—C13—C14—C18	176.79 (12)	C19—C21—C26—C25	179.11 (13)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O1i	0.95	2.50	3.4129 (16)	162
C7—H7···O4ii	1.00	2.49	3.1840 (16)	126
C20—H20C···O1iii	0.98	2.56	3.4948 (17)	161
C23—H23···O1iv	0.95	2.57	3.4847 (18)	161

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯O1i	0.95	2.50	3.4129 (16)	162
C7—H7⋯O4ii	1.00	2.49	3.1840 (16)	126
C20—H20C⋯O1iii	0.98	2.56	3.4948 (17)	161
C23—H23⋯O1iv	0.95	2.57	3.4847 (18)	161

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