2-(2-Carb-oxy-eth-yl)-1,3-dioxoisoindoline-5,6-dicarb-oxy-lic acid methanol monosolvate.

In the title compound, C(13)H(9)NO(8)·CH(3)OH, the main mol-ecule possesses three carb-oxy-lic acid groups, which are asymmetrically distributed around the mol-ecule core. This results in hydrogen-bonding motifs ranging from a chain to various rings. The combination of the chain motif together with a carb-oxy-lic dimer R(2) (2)(8) ring motif creates a ribbon of mol-ecules propagating along the c-axis direction. A second ribbon results from the combination of the chain motif together with a methanol solvent mol-ecule and carboxyl-containing R(4) (4)(12) ring motif. These two ribbons combine alternately, forming a hydrogen-bonded layer of mol-ecules parallel to (2[Formula: see text]0).

Related literature

For applications of charge-transfer complexes composed of pyromellitic anhydrides or their imides or polyimide derivatives, see: Barooah et al. (2006 ▶); Kim et al. (2002 ▶); O’Brien et al. (1988 ▶); Dingemans et al. (2004 ▶); Zheng et al. (2008 ▶). For an example of another asymmetrically substituted diimide, see: Zhu et al. (2010 ▶). For a description of the Cambridge Structural Database, see: Allen (2002 ▶). For the REAXYS database, see: Elsevier (2011 ▶). For graph-set analysis of hydrogen bonds, see: Etter et al. (1990 ▶); Bernstein et al. (1995 ▶).

Experimental

Crystal data

C13H9NO8·CH4O

M = 339.25

Triclinic,

a = 8.7830 (3) Å

b = 9.7262 (3) Å

c = 9.9157 (3) Å

α = 66.164 (2)°

β = 72.830 (2)°

γ = 77.926 (2)°

V = 736.35 (4) Å3

Z = 2

Mo Kα radiation

μ = 0.13 mm−1

T = 173 K

0.44 × 0.14 × 0.07 mm

Data collection

Bruker APEXII CCD diffractometer

11822 measured reflections

3549 independent reflections

2193 reflections with I > 2σ(I)

R int = 0.053

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.093

S = 0.89

3549 reflections

222 parameters

H-atom parameters constrained

Δρmax = 0.30 e Å−3

Δρmin = −0.23 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; 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 SCHAKAL99 (Keller, 1999 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811052755/bh2403sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811052755/bh2403Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811052755/bh2403Isup3.cml

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

C13H9NO8·CH4O	Z = 2
Mr = 339.25	F(000) = 352
Triclinic, P1	Dx = 1.530 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.7830 (3) Å	Cell parameters from 2207 reflections
b = 9.7262 (3) Å	θ = 2.3–26.5°
c = 9.9157 (3) Å	µ = 0.13 mm−1
α = 66.164 (2)°	T = 173 K
β = 72.830 (2)°	Needle, colourless
γ = 77.926 (2)°	0.44 × 0.14 × 0.07 mm
V = 736.35 (4) Å3

Bruker APEXII CCD diffractometer	2193 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.053
graphite	θmax = 28.0°, θmin = 2.3°
φ and ω scans	h = −11→11
11822 measured reflections	k = −12→12
3549 independent reflections	l = −13→13

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.093	H-atom parameters constrained
S = 0.89	w = 1/[σ2(Fo2) + (0.0403P)2] where P = (Fo2 + 2Fc2)/3
3549 reflections	(Δ/σ)max < 0.001
222 parameters	Δρmax = 0.30 e Å−3
0 restraints	Δρmin = −0.23 e Å−3
0 constraints

	x	y	z	Uiso*/Ueq
C1	0.9965 (2)	0.8792 (2)	−0.28914 (19)	0.0275 (4)
C2	0.9929 (2)	0.79281 (19)	−0.12438 (17)	0.0255 (4)
H2A	1.0792	0.8206	−0.0977	0.031*
H2B	1.0119	0.6831	−0.1046	0.031*
C3	0.8321 (2)	0.8275 (2)	−0.02696 (17)	0.0283 (4)
H3A	0.8179	0.9358	−0.0413	0.034*
H3B	0.7459	0.8090	−0.0614	0.034*
C4	0.8660 (2)	0.7795 (2)	0.23163 (18)	0.0256 (4)
C5	0.81809 (19)	0.66165 (18)	0.38558 (17)	0.0211 (4)
C6	0.74964 (19)	0.55402 (19)	0.37121 (18)	0.0217 (4)
C7	0.74729 (19)	0.60218 (19)	0.20843 (18)	0.0240 (4)
C8	0.83220 (19)	0.65153 (19)	0.52394 (17)	0.0226 (4)
H8	0.8806	0.7256	0.5322	0.027*
C9	0.77322 (19)	0.52920 (19)	0.65146 (17)	0.0208 (4)
C10	0.70651 (19)	0.41746 (18)	0.63744 (18)	0.0211 (4)
C11	0.69438 (19)	0.42998 (18)	0.49515 (17)	0.0232 (4)
H11	0.6494	0.3552	0.4845	0.028*
C12	0.7872 (2)	0.52609 (19)	0.80077 (18)	0.0234 (4)
C13	0.6457 (2)	0.28193 (19)	0.77029 (18)	0.0235 (4)
N1	0.81581 (16)	0.73687 (16)	0.13388 (14)	0.0243 (3)
O1	1.13876 (15)	0.87456 (16)	−0.38054 (13)	0.0387 (3)
H1	1.1320	0.9237	−0.4707	0.058*
O2	0.87748 (15)	0.94623 (17)	−0.33501 (13)	0.0441 (4)
O3	0.93188 (16)	0.89010 (14)	0.19466 (14)	0.0379 (3)
O4	0.69235 (14)	0.53863 (14)	0.15292 (12)	0.0312 (3)
O5	0.64890 (14)	0.55908 (16)	0.88490 (13)	0.0352 (3)
H5	0.6617	0.5507	0.9686	0.053*
O6	0.91487 (14)	0.50637 (15)	0.83081 (13)	0.0347 (3)
O7	0.69234 (15)	0.25746 (15)	0.89223 (13)	0.0371 (3)
H7	0.6421	0.1897	0.9661	0.056*
O8	0.56037 (15)	0.20381 (14)	0.76129 (13)	0.0339 (3)
C14	0.4653 (2)	−0.0897 (2)	0.7258 (2)	0.0445 (5)
H14A	0.4025	−0.0060	0.6629	0.067*
H14B	0.4247	−0.1853	0.7493	0.067*
H14C	0.5780	−0.0921	0.6706	0.067*
O9	0.45194 (18)	−0.06903 (15)	0.86241 (13)	0.0442 (4)
H9	0.4789	0.0164	0.8421	0.066*

	U11	U22	U33	U12	U13	U23
C1	0.0325 (10)	0.0322 (10)	0.0191 (9)	−0.0140 (9)	−0.0007 (8)	−0.0093 (8)
C2	0.0333 (10)	0.0245 (9)	0.0185 (9)	−0.0081 (8)	−0.0045 (7)	−0.0063 (8)
C3	0.0367 (10)	0.0311 (10)	0.0119 (9)	−0.0064 (8)	−0.0047 (7)	−0.0018 (8)
C4	0.0290 (10)	0.0273 (10)	0.0188 (9)	−0.0038 (8)	−0.0030 (7)	−0.0081 (8)
C5	0.0238 (9)	0.0221 (9)	0.0159 (9)	−0.0066 (7)	−0.0018 (7)	−0.0054 (7)
C6	0.0244 (9)	0.0260 (9)	0.0157 (8)	−0.0041 (7)	−0.0036 (7)	−0.0087 (7)
C7	0.0257 (9)	0.0299 (10)	0.0160 (9)	−0.0036 (8)	−0.0029 (7)	−0.0091 (8)
C8	0.0286 (9)	0.0243 (9)	0.0164 (9)	−0.0097 (8)	−0.0031 (7)	−0.0073 (7)
C9	0.0222 (9)	0.0254 (9)	0.0155 (8)	−0.0037 (7)	−0.0038 (6)	−0.0080 (7)
C10	0.0226 (9)	0.0225 (9)	0.0173 (9)	−0.0048 (7)	−0.0014 (7)	−0.0074 (7)
C11	0.0287 (9)	0.0237 (9)	0.0187 (9)	−0.0087 (8)	−0.0024 (7)	−0.0089 (8)
C12	0.0299 (10)	0.0241 (9)	0.0156 (9)	−0.0081 (8)	−0.0035 (7)	−0.0053 (7)
C13	0.0282 (9)	0.0235 (9)	0.0167 (9)	−0.0043 (8)	−0.0031 (7)	−0.0060 (8)
N1	0.0310 (8)	0.0269 (8)	0.0128 (7)	−0.0074 (7)	−0.0042 (6)	−0.0036 (6)
O1	0.0377 (8)	0.0503 (9)	0.0181 (7)	−0.0034 (6)	−0.0008 (5)	−0.0071 (7)
O2	0.0344 (8)	0.0690 (11)	0.0175 (7)	−0.0089 (7)	−0.0066 (6)	−0.0024 (7)
O3	0.0554 (9)	0.0322 (8)	0.0251 (7)	−0.0218 (7)	−0.0048 (6)	−0.0043 (6)
O4	0.0407 (8)	0.0404 (8)	0.0193 (7)	−0.0116 (6)	−0.0072 (5)	−0.0140 (6)
O5	0.0324 (7)	0.0571 (9)	0.0191 (7)	−0.0022 (6)	−0.0051 (5)	−0.0187 (7)
O6	0.0311 (7)	0.0506 (9)	0.0271 (7)	−0.0064 (6)	−0.0097 (6)	−0.0159 (7)
O7	0.0505 (8)	0.0376 (8)	0.0194 (7)	−0.0229 (7)	−0.0103 (6)	0.0036 (6)
O8	0.0465 (8)	0.0300 (7)	0.0269 (7)	−0.0198 (6)	−0.0057 (6)	−0.0066 (6)
C14	0.0469 (13)	0.0542 (14)	0.0352 (12)	−0.0073 (11)	−0.0103 (9)	−0.0176 (11)
O9	0.0705 (10)	0.0378 (9)	0.0234 (7)	−0.0297 (8)	−0.0035 (7)	−0.0038 (6)

C1—O2	1.217 (2)	C8—H8	0.9500
C1—O1	1.313 (2)	C9—C10	1.407 (2)
C1—C2	1.499 (2)	C9—C12	1.509 (2)
C2—C3	1.517 (2)	C10—C11	1.400 (2)
C2—H2A	0.9900	C10—C13	1.495 (2)
C2—H2B	0.9900	C11—H11	0.9500
C3—N1	1.4570 (19)	C12—O6	1.2013 (19)
C3—H3A	0.9900	C12—O5	1.3153 (19)
C3—H3B	0.9900	C13—O8	1.2159 (18)
C4—O3	1.2014 (19)	C13—O7	1.3062 (19)
C4—N1	1.399 (2)	O1—H1	0.8400
C4—C5	1.493 (2)	O5—H5	0.8400
C5—C8	1.376 (2)	O7—H7	0.8400
C5—C6	1.383 (2)	C14—O9	1.417 (2)
C6—C11	1.377 (2)	C14—H14A	0.9800
C6—C7	1.493 (2)	C14—H14B	0.9800
C7—O4	1.2142 (18)	C14—H14C	0.9800
C7—N1	1.382 (2)	O9—H9	0.8400
C8—C9	1.392 (2)
O2—C1—O1	122.62 (16)	C9—C8—H8	121.1
O2—C1—C2	122.97 (15)	C8—C9—C10	120.64 (14)
O1—C1—C2	114.40 (15)	C8—C9—C12	115.64 (14)
C1—C2—C3	110.35 (14)	C10—C9—C12	123.72 (14)
C1—C2—H2A	109.6	C11—C10—C9	120.38 (14)
C3—C2—H2A	109.6	C11—C10—C13	116.95 (14)
C1—C2—H2B	109.6	C9—C10—C13	122.67 (14)
C3—C2—H2B	109.6	C6—C11—C10	117.92 (14)
H2A—C2—H2B	108.1	C6—C11—H11	121.0
N1—C3—C2	112.98 (14)	C10—C11—H11	121.0
N1—C3—H3A	109.0	O6—C12—O5	125.07 (15)
C2—C3—H3A	109.0	O6—C12—C9	121.79 (15)
N1—C3—H3B	109.0	O5—C12—C9	112.91 (14)
C2—C3—H3B	109.0	O8—C13—O7	124.65 (15)
H3A—C3—H3B	107.8	O8—C13—C10	121.21 (15)
O3—C4—N1	125.36 (16)	O7—C13—C10	114.15 (14)
O3—C4—C5	129.03 (15)	C7—N1—C4	112.18 (13)
N1—C4—C5	105.61 (14)	C7—N1—C3	124.74 (13)
C8—C5—C6	121.89 (14)	C4—N1—C3	123.07 (14)
C8—C5—C4	130.10 (15)	C1—O1—H1	109.5
C6—C5—C4	108.01 (14)	C12—O5—H5	109.5
C11—C6—C5	121.31 (15)	C13—O7—H7	109.5
C11—C6—C7	130.59 (14)	O9—C14—H14A	109.5
C5—C6—C7	108.08 (14)	O9—C14—H14B	109.5
O4—C7—N1	126.69 (15)	H14A—C14—H14B	109.5
O4—C7—C6	127.21 (15)	O9—C14—H14C	109.5
N1—C7—C6	106.07 (13)	H14A—C14—H14C	109.5
C5—C8—C9	117.82 (14)	H14B—C14—H14C	109.5
C5—C8—H8	121.1	C14—O9—H9	109.5
O2—C1—C2—C3	−11.2 (2)	C5—C6—C11—C10	1.3 (2)
O1—C1—C2—C3	169.92 (14)	C7—C6—C11—C10	−177.13 (16)
C1—C2—C3—N1	174.94 (14)	C9—C10—C11—C6	0.1 (2)
O3—C4—C5—C8	2.3 (3)	C13—C10—C11—C6	179.96 (14)
N1—C4—C5—C8	−176.91 (16)	C8—C9—C12—O6	−67.8 (2)
O3—C4—C5—C6	−178.39 (18)	C10—C9—C12—O6	111.82 (19)
N1—C4—C5—C6	2.44 (18)	C8—C9—C12—O5	106.95 (17)
C8—C5—C6—C11	−1.0 (2)	C10—C9—C12—O5	−73.4 (2)
C4—C5—C6—C11	179.60 (15)	C11—C10—C13—O8	−14.9 (2)
C8—C5—C6—C7	177.76 (15)	C9—C10—C13—O8	164.96 (16)
C4—C5—C6—C7	−1.66 (18)	C11—C10—C13—O7	165.02 (15)
C11—C6—C7—O4	0.8 (3)	C9—C10—C13—O7	−15.1 (2)
C5—C6—C7—O4	−177.83 (17)	O4—C7—N1—C4	179.47 (17)
C11—C6—C7—N1	178.86 (17)	C6—C7—N1—C4	1.36 (18)
C5—C6—C7—N1	0.27 (18)	O4—C7—N1—C3	0.7 (3)
C6—C5—C8—C9	−0.7 (2)	C6—C7—N1—C3	−177.39 (14)
C4—C5—C8—C9	178.53 (16)	O3—C4—N1—C7	178.45 (17)
C5—C8—C9—C10	2.1 (2)	C5—C4—N1—C7	−2.34 (18)
C5—C8—C9—C12	−178.23 (15)	O3—C4—N1—C3	−2.8 (3)
C8—C9—C10—C11	−1.8 (2)	C5—C4—N1—C3	176.44 (14)
C12—C9—C10—C11	178.56 (16)	C2—C3—N1—C7	−93.99 (19)
C8—C9—C10—C13	178.31 (15)	C2—C3—N1—C4	87.39 (19)
C12—C9—C10—C13	−1.3 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2i	0.84	1.84	2.6784 (17)	172
O5—H5···O4ii	0.84	1.88	2.7181 (15)	178
O7—H7···O9iii	0.84	1.71	2.5360 (17)	168
O9—H9···O8	0.84	1.87	2.7014 (17)	169

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O2i	0.84	1.84	2.6784 (17)	172
O5—H5⋯O4ii	0.84	1.88	2.7181 (15)	178
O7—H7⋯O9iii	0.84	1.71	2.5360 (17)	168
O9—H9⋯O8	0.84	1.87	2.7014 (17)	169

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