The 1:1 adduct of caffeine and 2-(1,3-dioxoisoindolin-2-yl)acetic acid.

IN THE CRYSTAL STRUCTURE OF THE TITLE ADDUCT [SYSTEMATIC NAME: 2-(1,3-dioxoisoindolin-2-yl)acetic acid-1,3,7-trimethyl-1,2,3,6-tetra-hydro-7H-purine-2,6-dione (1/1)], C(8)H(10)N(4)O(2)·C(10)H(7)NO(4), the components are linked by an O-H⋯N hydrogen-bond and no proton transfer occurs.

Related literature

For background to N-phthaloylglycine and its derivatives, see: Antunes et al. (1998 ▶); Barooah et al. (2006a ▶,b ▶); Khan & Ismail (2002 ▶); Shariat & Abdollahi (2004 ▶); Yunus et al. (2008 ▶).

Experimental

Crystal data

C8H10N4O2·C10H7NO4

M = 399.37

Monoclinic,

a = 14.6595 (5) Å

b = 4.6567 (2) Å

c = 26.5281 (8) Å

β = 101.408 (2)°

V = 1775.16 (11) Å3

Z = 4

Mo Kα radiation

μ = 0.12 mm−1

T = 296 K

0.48 × 0.16 × 0.10 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2008b ▶) T min = 0.947, T max = 0.989

20916 measured reflections

3373 independent reflections

2268 reflections with I > 2σ(I)

R int = 0.045

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.130

S = 1.03

3373 reflections

269 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.20 e Å−3

Δρmin = −0.21 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: APEX2; data reduction: SAINT (Bruker, 2007 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008a ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008a ▶); molecular graphics: Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811030182/ds2126sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811030182/ds2126Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811030182/ds2126Isup3.cml

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

C8H10N4O2·C10H7NO4	F(000) = 832
Mr = 399.37	Dx = 1.494 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2850 reflections
a = 14.6595 (5) Å	θ = 2.9–23.0°
b = 4.6567 (2) Å	µ = 0.12 mm−1
c = 26.5281 (8) Å	T = 296 K
β = 101.408 (2)°	Needle, colourless
V = 1775.16 (11) Å3	0.48 × 0.16 × 0.10 mm
Z = 4

Bruker APEXII CCD diffractometer	3373 independent reflections
Radiation source: fine-focus sealed tube	2268 reflections with I > 2σ(I)
graphite	Rint = 0.045
ω and φ scan	θmax = 25.7°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 2008b)	h = −17→17
Tmin = 0.947, Tmax = 0.989	k = −5→5
20916 measured reflections	l = −32→32

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.130	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.0683P)2 + 0.2661P] where P = (Fo2 + 2Fc2)/3
3373 reflections	(Δ/σ)max = 0.005
269 parameters	Δρmax = 0.20 e Å−3
0 restraints	Δρmin = −0.21 e Å−3

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
O1	0.22787 (11)	0.5983 (3)	0.16097 (6)	0.0524 (4)
H1	0.293 (2)	0.537 (6)	0.1631 (11)	0.096 (9)*
O2	0.29779 (10)	0.9442 (3)	0.21235 (6)	0.0574 (4)
O3	−0.01236 (11)	0.5371 (4)	0.21311 (6)	0.0592 (4)
O4	0.08996 (11)	1.0227 (4)	0.08551 (6)	0.0630 (5)
O5	0.68437 (11)	0.0115 (4)	0.15118 (7)	0.0657 (5)
O6	0.42324 (13)	−0.2400 (4)	0.03383 (6)	0.0715 (5)
N1	0.05672 (10)	0.8102 (4)	0.15825 (6)	0.0416 (4)
N2	0.55660 (11)	0.4293 (4)	0.19480 (6)	0.0420 (4)
N3	0.55304 (13)	−0.1112 (4)	0.09235 (7)	0.0489 (5)
N4	0.40577 (12)	0.0946 (4)	0.09313 (6)	0.0440 (4)
N5	0.40629 (11)	0.4590 (4)	0.15872 (6)	0.0409 (4)
C1	0.22844 (14)	0.8265 (5)	0.19031 (8)	0.0408 (5)
C2	0.13310 (13)	0.9294 (5)	0.19542 (8)	0.0459 (5)
H2A	0.1237	0.8825	0.2297	0.055*
H2B	0.1313	1.1369	0.1922	0.055*
C3	0.04313 (14)	0.8602 (5)	0.10534 (8)	0.0451 (5)
C4	−0.03699 (14)	0.6796 (5)	0.08152 (8)	0.0430 (5)
C5	−0.07858 (17)	0.6416 (6)	0.03054 (9)	0.0577 (6)
H5	−0.0582	0.7406	0.0044	0.069*
C6	−0.15203 (19)	0.4493 (6)	0.02013 (10)	0.0683 (8)
H6	−0.1806	0.4149	−0.0139	0.082*
C7	−0.18374 (17)	0.3079 (6)	0.05892 (11)	0.0683 (7)
H7	−0.2340	0.1831	0.0505	0.082*
C8	−0.14258 (15)	0.3469 (5)	0.11024 (10)	0.0568 (6)
H8	−0.1640	0.2516	0.1364	0.068*
C9	−0.06796 (13)	0.5348 (5)	0.12049 (8)	0.0434 (5)
C10	−0.00813 (14)	0.6162 (5)	0.17002 (8)	0.0425 (5)
C11	0.47493 (14)	0.5566 (5)	0.19502 (8)	0.0420 (5)
H11	0.4670	0.6994	0.2183	0.050*
C12	0.54018 (13)	0.2291 (4)	0.15529 (7)	0.0389 (5)
C13	0.60057 (15)	0.0424 (5)	0.13510 (9)	0.0466 (6)
C14	0.45764 (16)	−0.0942 (5)	0.07064 (8)	0.0488 (6)
C15	0.44793 (13)	0.2549 (4)	0.13435 (7)	0.0372 (5)
C16	0.64351 (16)	0.4833 (6)	0.23127 (9)	0.0610 (7)
H16A	0.6928	0.5142	0.2128	0.073*
H16B	0.6582	0.3206	0.2536	0.073*
H16C	0.6366	0.6506	0.2513	0.073*
C17	0.60798 (19)	−0.3018 (6)	0.06585 (10)	0.0692 (8)
H17A	0.6630	−0.3617	0.0895	0.083*
H17B	0.6253	−0.2010	0.0376	0.083*
H17C	0.5715	−0.4673	0.0531	0.083*
C18	0.30650 (16)	0.1200 (6)	0.07221 (10)	0.0652 (7)
H18A	0.2970	0.1605	0.0361	0.078*
H18B	0.2810	0.2732	0.0893	0.078*
H18C	0.2761	−0.0569	0.0775	0.078*

	U11	U22	U33	U12	U13	U23
O1	0.0379 (9)	0.0535 (10)	0.0644 (10)	0.0043 (7)	0.0064 (7)	−0.0183 (8)
O2	0.0371 (9)	0.0605 (10)	0.0714 (11)	−0.0044 (8)	0.0033 (8)	−0.0154 (8)
O3	0.0578 (10)	0.0744 (11)	0.0468 (9)	0.0017 (9)	0.0134 (8)	0.0143 (8)
O4	0.0560 (10)	0.0731 (11)	0.0613 (11)	−0.0102 (9)	0.0155 (8)	0.0140 (9)
O5	0.0414 (10)	0.0730 (12)	0.0859 (13)	0.0115 (8)	0.0208 (9)	0.0056 (9)
O6	0.0895 (13)	0.0668 (12)	0.0590 (11)	−0.0085 (10)	0.0171 (9)	−0.0233 (10)
N1	0.0319 (9)	0.0526 (10)	0.0395 (10)	0.0017 (8)	0.0047 (7)	0.0017 (8)
N2	0.0363 (9)	0.0465 (10)	0.0430 (10)	−0.0046 (8)	0.0077 (8)	0.0009 (8)
N3	0.0544 (12)	0.0428 (10)	0.0551 (12)	0.0053 (9)	0.0244 (9)	−0.0002 (9)
N4	0.0429 (10)	0.0444 (10)	0.0441 (10)	−0.0007 (8)	0.0071 (8)	−0.0040 (9)
N5	0.0370 (9)	0.0433 (10)	0.0431 (10)	0.0023 (8)	0.0095 (8)	−0.0031 (8)
C1	0.0369 (11)	0.0441 (12)	0.0404 (12)	0.0010 (10)	0.0054 (9)	0.0014 (10)
C2	0.0374 (11)	0.0496 (13)	0.0489 (13)	0.0055 (10)	0.0043 (10)	−0.0073 (10)
C3	0.0381 (11)	0.0517 (13)	0.0464 (13)	0.0073 (10)	0.0105 (10)	0.0073 (11)
C4	0.0374 (11)	0.0473 (12)	0.0435 (12)	0.0077 (10)	0.0058 (9)	−0.0001 (10)
C5	0.0557 (14)	0.0676 (16)	0.0465 (14)	0.0128 (13)	0.0020 (11)	−0.0001 (12)
C6	0.0584 (16)	0.0771 (18)	0.0600 (17)	0.0108 (15)	−0.0113 (13)	−0.0173 (15)
C7	0.0463 (14)	0.0640 (17)	0.089 (2)	−0.0028 (13)	0.0006 (14)	−0.0178 (16)
C8	0.0416 (13)	0.0570 (15)	0.0723 (17)	−0.0018 (11)	0.0123 (12)	−0.0043 (13)
C9	0.0317 (11)	0.0460 (12)	0.0520 (13)	0.0060 (9)	0.0075 (10)	−0.0005 (10)
C10	0.0360 (11)	0.0482 (12)	0.0437 (13)	0.0096 (10)	0.0092 (9)	0.0049 (10)
C11	0.0456 (12)	0.0429 (12)	0.0396 (12)	−0.0009 (10)	0.0132 (10)	−0.0028 (10)
C12	0.0357 (11)	0.0398 (11)	0.0428 (12)	0.0008 (9)	0.0120 (9)	0.0016 (10)
C13	0.0422 (13)	0.0466 (13)	0.0544 (14)	0.0034 (10)	0.0180 (11)	0.0101 (11)
C14	0.0604 (15)	0.0434 (13)	0.0456 (13)	−0.0026 (11)	0.0178 (11)	−0.0010 (11)
C15	0.0382 (11)	0.0367 (11)	0.0382 (11)	−0.0005 (9)	0.0112 (9)	0.0003 (9)
C16	0.0437 (13)	0.0752 (17)	0.0599 (15)	−0.0102 (12)	−0.0005 (11)	−0.0039 (13)
C17	0.0885 (19)	0.0551 (15)	0.0776 (18)	0.0166 (14)	0.0492 (15)	0.0015 (14)
C18	0.0476 (14)	0.0845 (19)	0.0581 (15)	−0.0007 (14)	−0.0024 (11)	−0.0162 (14)

O1—C1	1.316 (2)	C3—C4	1.481 (3)
O1—H1	0.98 (3)	C4—C5	1.380 (3)
O2—C1	1.200 (2)	C4—C9	1.384 (3)
O3—C10	1.214 (2)	C5—C6	1.386 (4)
O4—C3	1.210 (2)	C5—H5	0.9300
O5—C13	1.227 (3)	C6—C7	1.378 (4)
O6—C14	1.214 (3)	C6—H6	0.9300
N1—C10	1.391 (3)	C7—C8	1.388 (3)
N1—C3	1.398 (3)	C7—H7	0.9300
N1—C2	1.448 (2)	C8—C9	1.385 (3)
N2—C11	1.337 (3)	C8—H8	0.9300
N2—C12	1.388 (3)	C9—C10	1.478 (3)
N2—C16	1.461 (3)	C11—H11	0.9300
N3—C13	1.404 (3)	C12—C15	1.362 (3)
N3—C14	1.405 (3)	C12—C13	1.419 (3)
N3—C17	1.468 (3)	C16—H16A	0.9600
N4—C15	1.367 (2)	C16—H16B	0.9600
N4—C14	1.374 (3)	C16—H16C	0.9600
N4—C18	1.456 (3)	C17—H17A	0.9600
N5—C11	1.328 (3)	C17—H17B	0.9600
N5—C15	1.360 (2)	C17—H17C	0.9600
C1—C2	1.509 (3)	C18—H18A	0.9600
C2—H2A	0.9700	C18—H18B	0.9600
C2—H2B	0.9700	C18—H18C	0.9600
C1—O1—H1	107.9 (17)	C7—C8—H8	121.7
C10—N1—C3	111.45 (17)	C4—C9—C8	121.6 (2)
C10—N1—C2	124.52 (17)	C4—C9—C10	108.32 (18)
C3—N1—C2	123.87 (17)	C8—C9—C10	130.1 (2)
C11—N2—C12	106.23 (16)	O3—C10—N1	125.0 (2)
C11—N2—C16	125.80 (19)	O3—C10—C9	128.9 (2)
C12—N2—C16	127.89 (18)	N1—C10—C9	106.19 (17)
C13—N3—C14	126.66 (18)	N5—C11—N2	113.31 (18)
C13—N3—C17	117.6 (2)	N5—C11—H11	123.3
C14—N3—C17	115.7 (2)	N2—C11—H11	123.3
C15—N4—C14	119.71 (18)	C15—C12—N2	105.00 (17)
C15—N4—C18	121.35 (18)	C15—C12—C13	122.92 (19)
C14—N4—C18	118.94 (19)	N2—C12—C13	131.95 (19)
C11—N5—C15	103.71 (16)	O5—C13—N3	121.6 (2)
O2—C1—O1	124.22 (19)	O5—C13—C12	126.7 (2)
O2—C1—C2	121.44 (19)	N3—C13—C12	111.71 (18)
O1—C1—C2	114.33 (18)	O6—C14—N4	122.0 (2)
N1—C2—C1	114.98 (17)	O6—C14—N3	121.3 (2)
N1—C2—H2A	108.5	N4—C14—N3	116.71 (19)
C1—C2—H2A	108.5	N5—C15—C12	111.75 (17)
N1—C2—H2B	108.5	N5—C15—N4	125.98 (18)
C1—C2—H2B	108.5	C12—C15—N4	122.25 (18)
H2A—C2—H2B	107.5	N2—C16—H16A	109.5
O4—C3—N1	124.1 (2)	N2—C16—H16B	109.5
O4—C3—C4	129.8 (2)	H16A—C16—H16B	109.5
N1—C3—C4	106.10 (17)	N2—C16—H16C	109.5
C5—C4—C9	121.5 (2)	H16A—C16—H16C	109.5
C5—C4—C3	130.5 (2)	H16B—C16—H16C	109.5
C9—C4—C3	107.92 (17)	N3—C17—H17A	109.5
C4—C5—C6	116.9 (2)	N3—C17—H17B	109.5
C4—C5—H5	121.5	H17A—C17—H17B	109.5
C6—C5—H5	121.5	N3—C17—H17C	109.5
C7—C6—C5	121.6 (2)	H17A—C17—H17C	109.5
C7—C6—H6	119.2	H17B—C17—H17C	109.5
C5—C6—H6	119.2	N4—C18—H18A	109.5
C6—C7—C8	121.7 (2)	N4—C18—H18B	109.5
C6—C7—H7	119.2	H18A—C18—H18B	109.5
C8—C7—H7	119.2	N4—C18—H18C	109.5
C9—C8—C7	116.6 (2)	H18A—C18—H18C	109.5
C9—C8—H8	121.7	H18B—C18—H18C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N5	0.98 (3)	1.73 (3)	2.707 (2)	171 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N5	0.98 (3)	1.73 (3)	2.707 (2)	171 (3)