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

The asymmetric unit of the title compound, C(22)H(16)N(2)O(4)·2CH(4)O, contains one half-mol-ecule and a methanol solvent mol-ecule. 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, inter-molecular O-H⋯O and N-H⋯O hydrogen bonds link the mol-ecules 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 = 436.20

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.070

wR(F 2) = 0.156

S = 1.04

2245 reflections

152 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.21 e Å−3

Δρmin = −0.25 e Å−3

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.

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

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

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

C22H16N2O4·2CH4O	F000 = 920
Mr = 436.20	Dx = 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 = 9–12º
b = 6.6300 (13) Å	µ = 0.09 mm−1
c = 20.215 (4) Å	T = 298 (2) K
β = 106.59 (3)º	Block, colorless
V = 2282.1 (9) Å3	0.30 × 0.20 × 0.10 mm
Z = 4

Enraf–Nonius CAD-4 diffractometer	Rint = 0.075
Radiation source: fine-focus sealed tube	θmax = 26.0º
Monochromator: graphite	θmin = 2.1º
T = 298(2) K	h = −21→21
ω/2θ scans	k = 0→8
Absorption correction: ψ scan(North et al., 1968)	l = −24→24
Tmin = 0.973, Tmax = 0.991	3 standard reflections
4477 measured reflections	every 120 min
2245 independent reflections	intensity decay: none
1050 reflections with I > 2σ(I)

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)] = 0.071	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.156	w = 1/[σ2(Fo2) + (0.0378P)2 + 1.8P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max < 0.001
2245 reflections	Δρmax = 0.21 e Å−3
152 parameters	Δρmin = −0.25 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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
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*

	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)

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)

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

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) ; (ii) .