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

Abdel-Aziz, A.A.-M.; El-Azab, A.S.; Alanazi, A.M.; Ng, S.W.; Tiekink, E.R.T.

doi:10.1107/S1600536812007684

organic compounds

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ISSN: 2056-9890

Volume 68| Part 3| March 2012| Page o907

doi:10.1107/S1600536812007684

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

Alaa A.-M. Abdel-Aziz,^a,^b ‡ Adel S. El-Azab,^a,^c Amer M. Alanazi,^a Seik Weng Ng ^d,^e and Edward R. T. Tiekink ^d ^*

^aDepartment of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, Riyadh 11451, Saudi Arabia, ^bDepartment of Medicinal Chemistry, Faculty of Pharmacy, University of Mansoura, Mansoura 35516, Egypt, ^cDepartment of Organic Chemistry, Faculty of Pharmacy, Al-Azhar University, Cairo 11884, Egypt, ^dDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, and ^eChemistry Department, Faculty of Science, King Abdulaziz University, PO Box 80203 Jeddah, Saudi Arabia
^*Correspondence e-mail: edward.tiekink@gmail.com

(Received 20 February 2012; accepted 20 February 2012; online 29 February 2012)

In the title compound, C₂₆H₂₀N₂O₄, 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, molecules are linked by C—H⋯O interactions; 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_r = 424.44
Monoclinic, P 2₁
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[F² > 2σ(F²)] = 0.033
wR(F²) = 0.099
S = 1.11
4093 reflections
289 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.25 e Å⁻³
Absolute structure: Flack (1983 ), 1898 Friedel pairs
Flack parameter: 0.08 (12)

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⋯O1^iv	0.95	2.57	3.4847 (18)	161
Symmetry codes: (i) x+1, y, z; (ii) $[-x+1, y+{\script{1\over 2}}, -z+2]$ ; (iii) $[-x, y-{\script{1\over 2}}, -z+1]$ ; (iv) $[-x-1, y-{\script{1\over 2}}, -z+1]$ .

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 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812007684/bt5823sup1.cif

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

Supporting information file. DOI: 10.1107/S1600536812007684/bt5823Isup3.cml

checkCIF report

Comment top

Recent work has shown that cyclic imides possess important biological potential, such as anti-hyperlipidemic, anti-diabetic, anti-tumour and anti-inflammatory activities (Abdel-Aziz, 2007; Abdel-Aziz, El-Azab et al., 2011; Abdel-Aziz, ElTahir et al., 2011). The title cyclic imide, 2,6-bis((S)-1-phenylethyl)pyrrolo[3,4-f]isoindole-1,3,5,7(2H,6H)-tetraone (I), was investigated during these trials and herein the crystal structure determination is described.

In (I), Fig. 1, the 12 atoms comprising the isoindole core are co-planar with a r.m.s. deviation for the fitted atoms of 0.043 Å. The maximum deviations from this least-squares plane are 0.043 (1) Å for the C15 and C16 atoms, and -0.058 (1) Å for the N2 atom. The phenyl rings lie to either side of the plane, forming dihedral angles of 88.64 (5)° [C1–C6] and 67.74 (6)° [C21–C26]; the dihedral angle between the phenyl rings = 63.39 (7)°.

Molecules are assembled in the crystal structure by C–H···O interactions, Fig. 2 and Table 1. Notably, one carbonyl-O atom is involved in a trifurcated H bond.

Related literature top

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 top

A solution of (+)-(S)-1-phenylethanamine (10 mmol) and benzene-1,2,4,5-tetracarboxylic dianhydride (10 mmol) in glacial acetic acid (10 ml) was heated under reflux for 12 h. After the evaporation of the reaction mixture to dryness under reduced pressure, the residue was neutralized using sodium bicarbonate solution (4%) until effervescence ceased. The precipitate obtained was washed with water, dried and recrystallized from MeOH/CHCl₃ (1:1 v/v). Yield 59%. M.pt: > 623 K. ¹H NMR (CDCl₃): δ 8.20 (s, 2H, Ar—H), 7.53–7.51 (d, 4H, J = 7.0 Hz, Ar—H), 7.38–7.35 (t, 4H, J = 7.0 Hz, Ar—H), 7.32–7.28 (q, 2H, J = 8.0 Hz, Ar—H), 5.62–5.61 (d, 2H, J = 6.0 Hz, 2CH), 1.98–1.96 (d, 6H, J = 6.0 Hz, 2CH₃). ¹³C NMR (CDCl₃): δ 166.02, 139.52, 137.05, 128.64, 128.07, 127.49, 118.19, 50.52, 17.41.

Computing details top

Data collection: CrysAlis PRO (Agilent, 2011); cell refinement: CrysAlis PRO (Agilent, 2011); data reduction: CrysAlis PRO (Agilent, 2011); 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).

Figures top

	Fig. 1. The molecular structure of (I) showing the atom-labelling scheme and displacement ellipsoids at the 50% probability level.
	Fig. 2. A view in projection down the a axis of the unit-cell contents for (I). The C—H···O interactions are shown as orange dashed lines.

2,6-Bis[(S)-1-phenylethyl]-1H,5H- pyrrolo[3,4-f]isoindole-1,3,5,7(2H,6H)-tetrone top

Crystal data top

C₂₆H₂₀N₂O₄	F(000) = 444
M_r = 424.44	D_x = 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

Data collection top

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	R_int = 0.018
Detector resolution: 10.4041 pixels mm^-1	θ_max = 76.7°, θ_min = 3.9°
ω scan	h = −7→7
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	k = −20→20
T_min = 0.656, T_max = 1.000	l = −14→13
7858 measured reflections

Refinement top

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(F_o²) + (0.0781P)² + 0.0806P] where P = (F_o² + 2F_c²)/3
S = 1.11	(Δ/σ)_max < 0.001
4093 reflections	Δρ_max = 0.24 e Å⁻³
289 parameters	Δρ_min = −0.25 e Å⁻³
1 restraint	Absolute structure: Flack (1983), 1898 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.08 (12)

Crystal data top

C₂₆H₂₀N₂O₄	V = 1018.29 (3) Å³
M_r = 424.44	Z = 2
Monoclinic, P2₁	Cu Kα radiation
a = 5.6401 (1) Å	µ = 0.77 mm⁻¹
b = 16.1040 (2) Å	T = 100 K
c = 11.3759 (2) Å	0.30 × 0.25 × 0.20 mm
β = 99.762 (2)°

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	4093 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	4091 reflections with I > 2σ(I)
T_min = 0.656, T_max = 1.000	R_int = 0.018
7858 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.033	H-atom parameters constrained
wR(F²) = 0.099	Δρ_max = 0.24 e Å⁻³
S = 1.11	Δρ_min = −0.25 e Å⁻³
4093 reflections	Absolute structure: Flack (1983), 1898 Friedel pairs
289 parameters	Absolute structure parameter: 0.08 (12)
1 restraint

Special details top

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.

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

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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···O1^iv	0.95	2.57	3.4847 (18)	161

Symmetry codes: (i) x+1, y, z; (ii) −x+1, y+1/2, −z+2; (iii) −x, y−1/2, −z+1; (iv) −x−1, y−1/2, −z+1.

Experimental details

Crystal data
Chemical formula	C₂₆H₂₀N₂O₄
M_r	424.44
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	100
a, b, c (Å)	5.6401 (1), 16.1040 (2), 11.3759 (2)
β (°)	99.762 (2)
V (Å³)	1018.29 (3)
Z	2
Radiation type	Cu Kα
µ (mm⁻¹)	0.77
Crystal size (mm)	0.30 × 0.25 × 0.20

Data collection
Diffractometer	Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2011)
T_min, T_max	0.656, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	7858, 4093, 4091
R_int	0.018
(sin θ/λ)_max (Å⁻¹)	0.631

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.033, 0.099, 1.11
No. of reflections	4093
No. of parameters	289
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.24, −0.25
Absolute structure	Flack (1983), 1898 Friedel pairs
Absolute structure parameter	0.08 (12)

Computer programs: CrysAlis PRO (Agilent, 2011), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

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···O1^iv	0.95	2.57	3.4847 (18)	161

Symmetry codes: (i) x+1, y, z; (ii) −x+1, y+1/2, −z+2; (iii) −x, y−1/2, −z+1; (iv) −x−1, y−1/2, −z+1.

Footnotes

‡Additional correspondence author, e-mail: alaa_moenes@yahoo.com.

Acknowledgements

The authors extend their appreciation to the Deanship of Scientific Research at King Saud University for funding the work through the research group project (No. RGP-VPP-163). We also thank the Ministry of Higher Education (Malaysia) for funding structural studies through the High-Impact Research scheme (UM.C/HIR/MOHE/SC/12).

References

Abdel-Aziz, A. A.-M. (2007). Eur. J. Med. Chem. 42, 614–626. Web of Science PubMed CAS Google Scholar
Abdel-Aziz, A. A.-M., El-Azab, A. S., Attia, S. M., Al-Obaid, A. M., Al-Omar, M. A. & El-Subbagh, H. I. (2011). Eur. J. Med. Chem. 46, 4324–4329. Web of Science CAS PubMed Google Scholar
Abdel-Aziz, A. A.-M., ElTahir, K. E. H. & Asiri, Y. A. (2011). Eur. J. Med. Chem. 46, 1648–1655. Web of Science CAS PubMed Google Scholar
Agilent (2011). CrysAlis PRO. Agilent Technologies, Yarnton, Oxfordshire, England. Google Scholar
Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 68| Part 3| March 2012| Page o907

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Footnotes

Acknowledgements

References

organic compounds

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