3,7-Dihydr­oxy-3,7-diphenyl-2H,6H-pyrrolo[3,4-f]isoindole-1,5(3H,7H)-dione methanol disolvate

Liu, S.; Liu, J.-N.; Jiang, P.; Chu, Q.-Y.; Zhu, H.-J.

doi:10.1107/S1600536808039445

organic compounds

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Volume 64| Part 12| December 2008| Page o2479

doi:10.1107/S1600536808039445

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3,7-Dihydroxy-3,7-diphenyl-2H,6H-pyrrolo[3,4-f]isoindole-1,5(3H,7H)-dione methanol disolvate

Shan Liu,^a Jing-Ning Liu,^b Peng Jiang,^a Qing-Yan Chu ^a and Hong-Jun Zhu ^a ^*

^aDepartment of Applied Chemistry, College of Science, Nanjing University of Technology, Nanjing 210009, People's Republic of China, and ^bDepartment of Public Security Science, Jiangsu Police Institute, Nanjing 210012, People's Republic of China
^*Correspondence e-mail: zhuhj@njut.edu.cn

(Received 17 November 2008; accepted 24 November 2008; online 29 November 2008)

The asymmetric unit of the title compound, C₂₂H₁₆N₂O₄·2CH₄O, contains one half-molecule and a methanol solvent molecule. The aromatic ring is oriented at a dihedral angle of 82.91 (3)° with respect to the planar indole ring systems. In the crystal structure, intermolecular O—H⋯O and N—H⋯O hydrogen bonds link the molecules into chains along the b axis.

Related literature

For general background, see: Antoniadis et al. (1994 ); Kolosov et al. (2002 ); Tonzola et al. (2003 ). For a related structure, see: Liu et al. (2008 ). For bond-length data, see: Allen et al. (1987 ).

Experimental

Crystal data

C₂₂H₁₆N₂O₄·2CH₄O
M_r = 436.20
Monoclinic, C 2/c
a = 17.767 (4) Å
b = 6.6300 (13) Å
c = 20.215 (4) Å
β = 106.59 (3)°
V = 2282.1 (9) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 298 (2) K
0.30 × 0.20 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: ψ scan (North et al., 1968 ) T_min = 0.973, T_max = 0.991
4477 measured reflections
2245 independent reflections
1050 reflections with I > 2σ(I)
R_int = 0.075
3 standard reflections frequency: 120 min intensity decay: none

Refinement

R[F² > 2σ(F²)] = 0.070
wR(F²) = 0.156
S = 1.04
2245 reflections
152 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.25 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O3	0.82	1.86	2.633 (4)	156
O3—H3⋯O2ⁱ	0.82	1.94	2.719 (4)	158
N—H⋯O1ⁱⁱ	0.84 (4)	2.08 (4)	2.907 (4)	170
Symmetry codes: (i) x, y+1, z; (ii) -x, -y+1, -z+1.

Data collection: CAD-4 Software (Enraf–Nonius, 1985 ); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995 ); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808039445/hk2579sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808039445/hk2579Isup2.hkl

checkCIF report

Comment top

The title compound is an important intermediate used to synthesize the monomer 2,5-dibenzoyl-1,4-phenylenediamine, which can be utilized to synthesize organic semiconductors and conjugated polymers (Tonzola et al., 2003), which are of wide current interest for applications in electronic and optoelectronic devices including light-emitting diodes (Kolosov et al., 2002), thin film transistors and photovoltaic cells (Antoniadis et al., 1994). We report herein the crystal structure of the title compound, which is of interest to us in the field.

The asymmetric unit of the title compound (Fig. 1) contains one-half molecule and a methanol molecule, where the bond lengths (Allen et al., 1987) and angles are within normal ranges. Rings A (C1-C6), B (N/C7-C8/C11A) and C (C9-C11/C9A-C11A) are, of course, planar, and the dihedral angle between rings B and C is B/C = 1.66 (3)° [symmetry code: (A) 1/2 - x, 3/2 - y, 1 - z]. So, the indole ring is essentially planar. Ring A is oriented with respect to the planar indole ring at a dihedral angle of 82.91 (3)°. The intramolecular C-H···O hydrogen bond (Table 1) results in the formation of a nonplanar five-membered ring D (O1/C1/C6/C7/H1B) adopting envelope conformation with O1 atom displaced by 0.288 (3) Å from the plane of the other ring atoms.

In the crystal structure, intermolecular O-H···O and N-H···O hydrogen bonds (Table 1) link the molecules into chains along b axis (Fig. 2), in which they may be effective in the stabilization of the structure.

Related literature top

For general background, see: Antoniadis et al. (1994); Kolosov et al. (2002); Tonzola et al. (2003). For a related structure, see: Liu et al. (2008). For bond-length data, see: Allen et al. (1987).

Experimental top

The title compound was prepared according to the literature method (Liu et al., 2008). Crystals suitable for X-ray analysis were obtained by dissolving the title compound (0.5 g) in methanol (50 ml), and evaporating the solvent slowly at room temperature for about 30 d.

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1985); cell refinement: CAD-4 Software (Enraf–Nonius, 1985); data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 40% probability level [symmetry code: (A) 1/2 - x, 3/2 - y, 1 - z]. Hydrogen bonds are shown as dashed lines.
	Fig. 2. A partial packing diagram of the title compound. Hydrogen bonds are shown as dashed lines.

3,7-Dihydroxy-3,7-diphenyl-2H,6H-pyrrolo[3,4-f]isoindole- 1,5(3H,7H)-dione methanol disolvate top

Crystal data top

C₂₂H₁₆N₂O₄·2CH₄O	F(000) = 920
M_r = 436.20	D_x = 1.270 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 25 reflections
a = 17.767 (4) Å	θ = 9–12°
b = 6.6300 (13) Å	µ = 0.09 mm⁻¹
c = 20.215 (4) Å	T = 298 K
β = 106.59 (3)°	Block, colorless
V = 2282.1 (9) Å³	0.30 × 0.20 × 0.10 mm
Z = 4

Data collection top

Enraf–Nonius CAD-4 diffractometer	1050 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.075
Graphite monochromator	θ_max = 26.0°, θ_min = 2.1°
ω/2θ scans	h = −21→21
Absorption correction: ψ scan (North et al., 1968)	k = 0→8
T_min = 0.973, T_max = 0.991	l = −24→24
4477 measured reflections	3 standard reflections every 120 min
2245 independent reflections	intensity decay: none

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)] = 0.071	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.156	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ²(F_o²) + (0.0378P)² + 1.8P] where P = (F_o² + 2F_c²)/3
2245 reflections	(Δ/σ)_max < 0.001
152 parameters	Δρ_max = 0.21 e Å⁻³
0 restraints	Δρ_min = −0.25 e Å⁻³

Crystal data top

C₂₂H₁₆N₂O₄·2CH₄O	V = 2282.1 (9) Å³
M_r = 436.20	Z = 4
Monoclinic, C2/c	Mo Kα radiation
a = 17.767 (4) Å	µ = 0.09 mm⁻¹
b = 6.6300 (13) Å	T = 298 K
c = 20.215 (4) Å	0.30 × 0.20 × 0.10 mm
β = 106.59 (3)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	1050 reflections with I > 2σ(I)
Absorption correction: ψ scan (North et al., 1968)	R_int = 0.075
T_min = 0.973, T_max = 0.991	3 standard reflections every 120 min
4477 measured reflections	intensity decay: none
2245 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.071	0 restraints
wR(F²) = 0.156	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 0.21 e Å⁻³
2245 reflections	Δρ_min = −0.25 e Å⁻³
152 parameters

Special details top

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
N	0.10301 (18)	0.4308 (5)	0.49495 (17)	0.0429 (13)
H	0.060 (2)	0.372 (5)	0.4881 (17)	0.042 (11)*
O1	0.04932 (13)	0.7469 (4)	0.51464 (13)	0.0451 (7)
H1	0.0443	0.7801	0.4745	0.068*
O2	0.15728 (14)	0.2655 (4)	0.41962 (14)	0.0537 (8)
O3	0.05976 (17)	0.9420 (4)	0.40414 (15)	0.0657 (9)
H3	0.0982	1.0163	0.4117	0.099*
C1	0.0891 (3)	0.6807 (7)	0.6511 (2)	0.0689 (14)
H1B	0.0549	0.7834	0.6302	0.083*
C2	0.1022 (3)	0.6438 (10)	0.7205 (3)	0.0911 (18)
H2A	0.0771	0.7224	0.7459	0.109*
C3	0.1513 (3)	0.4939 (10)	0.7521 (3)	0.0879 (17)
H3A	0.1597	0.4684	0.7989	0.106*
C4	0.1878 (3)	0.3827 (8)	0.7149 (3)	0.0908 (17)
H4A	0.2218	0.2802	0.7362	0.109*
C5	0.1753 (3)	0.4194 (7)	0.6454 (2)	0.0721 (14)
H5A	0.2009	0.3412	0.6204	0.086*
C6	0.12522 (19)	0.5704 (6)	0.61275 (19)	0.0404 (10)
C7	0.11403 (18)	0.6157 (5)	0.53721 (19)	0.0373 (9)
C8	0.15509 (19)	0.4032 (6)	0.45934 (19)	0.0392 (9)
C9	0.21057 (18)	0.5789 (5)	0.47727 (17)	0.0343 (9)
C10	0.27381 (18)	0.6211 (5)	0.45295 (18)	0.0364 (9)
H10A	0.2892	0.5363	0.4225	0.044*
C11	0.31286 (17)	0.7995 (5)	0.47725 (18)	0.0325 (8)
C12	0.0478 (4)	0.8537 (9)	0.3413 (3)	0.127 (3)
H12A	0.0132	0.7406	0.3377	0.191*
H12B	0.0971	0.8085	0.3361	0.191*
H12C	0.0247	0.9497	0.3058	0.191*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0334 (13)	0.0397 (16)	0.0656 (19)	−0.0020 (12)	0.0198 (13)	0.0084 (14)
O2	0.0631 (17)	0.0341 (16)	0.0733 (19)	−0.0195 (14)	0.0342 (15)	−0.0183 (15)
O3	0.078 (2)	0.0487 (19)	0.067 (2)	−0.0248 (16)	0.0150 (17)	0.0023 (16)
N	0.037 (2)	0.0300 (19)	0.068 (3)	−0.0188 (15)	0.0243 (18)	−0.0108 (16)
C1	0.067 (3)	0.080 (4)	0.066 (3)	0.022 (3)	0.030 (3)	0.006 (3)
C2	0.088 (4)	0.128 (5)	0.065 (4)	0.025 (4)	0.034 (3)	−0.010 (4)
C3	0.092 (4)	0.116 (5)	0.060 (4)	−0.015 (4)	0.028 (3)	0.011 (4)
C4	0.118 (5)	0.072 (4)	0.075 (4)	0.022 (3)	0.017 (3)	0.029 (3)
C5	0.096 (4)	0.049 (3)	0.074 (3)	0.020 (3)	0.029 (3)	0.006 (3)
C6	0.0344 (19)	0.036 (2)	0.057 (3)	−0.0061 (18)	0.0232 (19)	0.001 (2)
C7	0.0263 (17)	0.0260 (19)	0.063 (3)	−0.0051 (16)	0.0189 (18)	−0.0024 (19)
C8	0.039 (2)	0.030 (2)	0.051 (2)	−0.0055 (18)	0.0179 (19)	0.001 (2)
C9	0.0321 (18)	0.027 (2)	0.044 (2)	−0.0042 (16)	0.0120 (17)	−0.0015 (18)
C10	0.0365 (19)	0.0251 (19)	0.053 (2)	−0.0032 (17)	0.0222 (17)	−0.0049 (18)
C11	0.0281 (18)	0.0277 (19)	0.045 (2)	−0.0066 (15)	0.0161 (16)	−0.0002 (17)
C12	0.223 (8)	0.071 (4)	0.077 (4)	−0.022 (5)	0.026 (5)	−0.020 (3)

Geometric parameters (Å, º) top

N—C8	1.337 (4)	C6—C7	1.512 (5)
N—C7	1.475 (4)	C7—O1	1.410 (4)
N—H	0.84 (4)	C7—C11ⁱ	1.518 (4)
O1—H1	0.8200	C8—O2	1.224 (4)
O3—H3	0.8200	C8—C9	1.502 (5)
C1—C6	1.353 (5)	C9—C11ⁱ	1.373 (4)
C1—C2	1.377 (6)	C9—C10	1.378 (4)
C1—H1B	0.9300	C10—C11	1.389 (4)
C2—C3	1.357 (7)	C10—H10A	0.9300
C2—H2A	0.9300	C11—C9ⁱ	1.373 (4)
C3—C4	1.344 (7)	C11—C7ⁱ	1.518 (4)
C3—H3A	0.9300	C12—O3	1.359 (5)
C4—C5	1.380 (6)	C12—H12A	0.9600
C4—H4A	0.9300	C12—H12B	0.9600
C5—C6	1.376 (5)	C12—H12C	0.9600
C5—H5A	0.9300

C8—N—C7	115.3 (3)	O1—C7—C6	108.0 (3)
C8—N—H	126 (2)	N—C7—C6	112.2 (3)
C7—N—H	116 (2)	O1—C7—C11ⁱ	111.9 (3)
C7—O1—H1	109.5	N—C7—C11ⁱ	100.1 (3)
C12—O3—H3	109.5	C6—C7—C11ⁱ	113.3 (3)
C6—C1—C2	121.2 (5)	O2—C8—N	127.7 (3)
C6—C1—H1B	119.4	O2—C8—C9	126.5 (3)
C2—C1—H1B	119.4	N—C8—C9	105.7 (3)
C3—C2—C1	120.6 (5)	C11ⁱ—C9—C10	123.6 (3)
C3—C2—H2A	119.7	C11ⁱ—C9—C8	108.3 (3)
C1—C2—H2A	119.7	C10—C9—C8	128.1 (3)
C4—C3—C2	119.1 (5)	C9—C10—C11	115.0 (3)
C4—C3—H3A	120.5	C9—C10—H10A	122.5
C2—C3—H3A	120.5	C11—C10—H10A	122.5
C3—C4—C5	120.6 (5)	C9ⁱ—C11—C10	121.4 (3)
C3—C4—H4A	119.7	C9ⁱ—C11—C7ⁱ	110.6 (3)
C5—C4—H4A	119.7	C10—C11—C7ⁱ	128.0 (3)
C6—C5—C4	120.7 (4)	O3—C12—H12A	109.5
C6—C5—H5A	119.6	O3—C12—H12B	109.5
C4—C5—H5A	119.6	H12A—C12—H12B	109.5
C1—C6—C5	117.7 (4)	O3—C12—H12C	109.5
C1—C6—C7	121.6 (4)	H12A—C12—H12C	109.5
C5—C6—C7	120.6 (3)	H12B—C12—H12C	109.5
O1—C7—N	111.4 (3)

C6—C1—C2—C3	−0.5 (8)	C5—C6—C7—N	45.5 (4)
C1—C2—C3—C4	0.6 (9)	C1—C6—C7—C11ⁱ	110.5 (4)
C2—C3—C4—C5	−0.4 (9)	C5—C6—C7—C11ⁱ	−66.9 (4)
C3—C4—C5—C6	0.0 (8)	C7—N—C8—O2	−178.1 (4)
C2—C1—C6—C5	0.2 (7)	C7—N—C8—C9	1.1 (4)
C2—C1—C6—C7	−177.3 (4)	O2—C8—C9—C11ⁱ	179.1 (4)
C4—C5—C6—C1	0.1 (7)	N—C8—C9—C11ⁱ	−0.1 (4)
C4—C5—C6—C7	177.6 (4)	O2—C8—C9—C10	0.3 (6)
C8—N—C7—O1	116.9 (3)	N—C8—C9—C10	−178.9 (4)
C8—N—C7—C6	−122.0 (3)	C11ⁱ—C9—C10—C11	−0.7 (6)
C8—N—C7—C11ⁱ	−1.6 (4)	C8—C9—C10—C11	177.9 (3)
C1—C6—C7—O1	−14.0 (5)	C9—C10—C11—C9ⁱ	0.7 (6)
C5—C6—C7—O1	168.6 (3)	C9—C10—C11—C7ⁱ	177.4 (3)
C1—C6—C7—N	−137.1 (4)

Symmetry code: (i) −x+1/2, −y+3/2, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O3	0.82	1.86	2.633 (4)	156
O3—H3···O2ⁱⁱ	0.82	1.94	2.719 (4)	158
N—H···O1ⁱⁱⁱ	0.84 (4)	2.08 (4)	2.907 (4)	170
C1—H1B···O1	0.93	2.32	2.681 (5)	102

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

Experimental details

Crystal data
Chemical formula	C₂₂H₁₆N₂O₄·2CH₄O
M_r	436.20
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	298
a, b, c (Å)	17.767 (4), 6.6300 (13), 20.215 (4)
β (°)	106.59 (3)
V (Å³)	2282.1 (9)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.30 × 0.20 × 0.10

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.973, 0.991
No. of measured, independent and observed [I > 2σ(I)] reflections	4477, 2245, 1050
R_int	0.075
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.071, 0.156, 1.04
No. of reflections	2245
No. of parameters	152
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.21, −0.25

Computer programs: CAD-4 Software (Enraf–Nonius, 1985), XCAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O3	0.82	1.86	2.633 (4)	156
O3—H3···O2ⁱ	0.82	1.94	2.719 (4)	158
N—H···O1ⁱⁱ	0.84 (4)	2.08 (4)	2.907 (4)	170
C1—H1B···O1	0.93	2.32	2.681 (5)	102

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

Acknowledgements

This work was supported by the Science Fundamental Research Fund of the Education Department, Jiangsu Province (grant No. 06KJB150024). The authors thank the Center of Testing and Analysis, Nanjing University, for the data collection.

References

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

3,7-Dihydr­­oxy-3,7-di­phenyl-2H,6H-pyrrolo[3,4-f]iso­indole-1,5(3H,7H)-dione methanol disolvate

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

3,7-Dihydroxy-3,7-diphenyl-2H,6H-pyrrolo[3,4-f]isoindole-1,5(3H,7H)-dione methanol disolvate