Caffeine-N-phthaloyl-β-alanine (1/1).

The title co-crystal [systematic name: 3-(1,3-dioxoisoindolin-2-yl)propanoic acid-1,3,7-trimethyl-1H-purine-2,6(3H,7H)-dione (1/1)], C(8)H(10)N(4)O(2)·C(11)H(9)NO(4), is the combination of 1:1 adduct of N-phthaloyl-β-alanine with caffeine. The phthalimide and purine rings in the N-phthaloyl-β-alanine and caffeine mol-ecules are essentially planar, with r.m.s. deviations of the fitted atoms of 0.0078 and 0.0118 Å, respectively. In the crystal, the two mol-ecules are linked via an O-H⋯N hydrogen bond involving the intact carb-oxy-lic acid (COOH) group. The crystal structure is consolidated by C-H⋯O inter-actions. The H atoms of a methyl group of the caffeine mol-ecule are disordered over two sets of sites of equal occupancy.

Related literature

For related structures, see: Bhatti et al. (2011 ▶); Feeder & Jones (1996 ▶).

Experimental

Crystal data

C8H10N4O2·C11H9NO4

M = 413.39

Triclinic,

a = 8.3411 (17) Å

b = 9.0638 (18) Å

c = 13.162 (3) Å

α = 77.105 (4)°

β = 82.394 (4)°

γ = 72.865 (4)°

V = 924.6 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.11 mm−1

T = 130 K

0.42 × 0.40 × 0.35 mm

Data collection

Bruker SMART APEX diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ▶) T min = 0.954, T max = 0.962

8826 measured reflections

4378 independent reflections

3752 reflections with I > 2σ(I)

R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.106

S = 1.03

4378 reflections

277 parameters

H-atom parameters constrained

Δρmax = 0.26 e Å−3

Δρmin = −0.26 e Å−3

Data collection: SMART (Bruker, 2002 ▶); cell refinement: SAINT (Bruker, 2002 ▶); data reduction: SAINT; 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 and local programs.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812022696/pv2544sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812022696/pv2544Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812022696/pv2544Isup3.cml

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

C8H10N4O2·C11H9NO4	Z = 2
Mr = 413.39	F(000) = 432
Triclinic, P1	Dx = 1.485 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.3411 (17) Å	Cell parameters from 3614 reflections
b = 9.0638 (18) Å	θ = 2.6–28.2°
c = 13.162 (3) Å	µ = 0.11 mm−1
α = 77.105 (4)°	T = 130 K
β = 82.394 (4)°	Block, colourless
γ = 72.865 (4)°	0.42 × 0.40 × 0.35 mm
V = 924.6 (3) Å3

Bruker SMART APEX diffractometer	4378 independent reflections
Radiation source: sealed tube	3752 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.022
φ and ω scans	θmax = 27.9°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −10→10
Tmin = 0.954, Tmax = 0.962	k = −11→11
8826 measured reflections	l = −17→17

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.039	H-atom parameters constrained
wR(F2) = 0.106	w = 1/[σ2(Fo2) + (0.0581P)2 + 0.1919P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max < 0.001
4378 reflections	Δρmax = 0.26 e Å−3
277 parameters	Δρmin = −0.26 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0023 (15)

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	Occ. (<1)
O1	0.27140 (12)	0.71481 (11)	0.44923 (7)	0.0325 (2)
O2	0.44166 (11)	0.89747 (10)	0.70215 (7)	0.0269 (2)
O3	0.39875 (12)	0.24964 (10)	0.74716 (7)	0.0289 (2)
O4	0.49142 (12)	0.38406 (10)	0.83878 (7)	0.0289 (2)
H4	0.5451	0.2935	0.8673	0.043*
N1	0.37128 (13)	0.76999 (12)	0.58804 (8)	0.0228 (2)
C1	0.28998 (15)	0.80945 (15)	0.49543 (9)	0.0236 (2)
C2	0.23764 (14)	0.98470 (14)	0.46992 (9)	0.0223 (2)
C3	0.15355 (15)	1.08616 (16)	0.38653 (10)	0.0273 (3)
H3A	0.1171	1.0480	0.3346	0.033*
C4	0.12468 (15)	1.24709 (16)	0.38213 (10)	0.0290 (3)
H4A	0.0670	1.3201	0.3261	0.035*
C5	0.17853 (15)	1.30301 (15)	0.45800 (10)	0.0279 (3)
H5A	0.1573	1.4133	0.4526	0.034*
C6	0.26336 (15)	1.19969 (15)	0.54206 (10)	0.0247 (3)
H6A	0.3006	1.2372	0.5941	0.030*
C7	0.29048 (14)	1.04076 (14)	0.54603 (9)	0.0215 (2)
C8	0.37667 (14)	0.90240 (14)	0.62382 (9)	0.0214 (2)
C9	0.44832 (15)	0.61010 (14)	0.63967 (10)	0.0236 (2)
H9A	0.5306	0.6112	0.6870	0.028*
H9B	0.5099	0.5479	0.5866	0.028*
C10	0.31773 (15)	0.53188 (14)	0.70237 (10)	0.0239 (3)
H10A	0.2477	0.5993	0.7505	0.029*
H10B	0.2431	0.5189	0.6544	0.029*
C11	0.40448 (14)	0.37333 (14)	0.76419 (9)	0.0219 (2)
O5	0.05201 (12)	−0.05872 (12)	0.78890 (7)	0.0323 (2)
O6	0.06764 (11)	0.39207 (10)	0.88703 (7)	0.0292 (2)
N2	0.28028 (12)	0.17054 (11)	1.06458 (8)	0.0210 (2)
N3	0.34827 (12)	−0.08987 (12)	1.07618 (8)	0.0211 (2)
N4	0.19842 (12)	−0.08902 (12)	0.92895 (8)	0.0225 (2)
N5	0.05480 (12)	0.16501 (12)	0.84150 (8)	0.0246 (2)
C20	0.27113 (17)	0.32244 (15)	1.08893 (11)	0.0292 (3)
H20A	0.3295	0.3056	1.1522	0.044*
H20B	0.1530	0.3804	1.1004	0.044*
H20C	0.3247	0.3833	1.0305	0.044*
C21	0.36256 (14)	0.02847 (13)	1.11659 (9)	0.0214 (2)
H21A	0.4241	0.0136	1.1756	0.026*
C22	0.25050 (14)	−0.01704 (14)	0.99472 (9)	0.0196 (2)
C23	0.25004 (16)	−0.26028 (15)	0.93844 (10)	0.0273 (3)
H23A	0.3469	−0.2903	0.8890	0.041*
H23B	0.1567	−0.2948	0.9229	0.041*
H23C	0.2811	−0.3105	1.0098	0.041*
C24	0.09971 (14)	0.00176 (15)	0.84884 (9)	0.0239 (3)
C25	−0.04962 (17)	0.26056 (18)	0.75566 (10)	0.0330 (3)
H25A	−0.0890	0.3702	0.7647	0.050*	0.50
H25B	−0.1466	0.2202	0.7562	0.050*	0.50
H25C	0.0172	0.2549	0.6888	0.050*	0.50
H25D	−0.0567	0.1933	0.7085	0.050*	0.50
H25E	0.0010	0.3434	0.7170	0.050*	0.50
H25F	−0.1628	0.3086	0.7844	0.050*	0.50
C26	0.10740 (14)	0.24778 (14)	0.90378 (9)	0.0226 (2)
C27	0.20625 (14)	0.14314 (14)	0.98483 (9)	0.0206 (2)

	U11	U22	U33	U12	U13	U23
O1	0.0409 (5)	0.0297 (5)	0.0309 (5)	−0.0097 (4)	−0.0096 (4)	−0.0099 (4)
O2	0.0321 (5)	0.0264 (5)	0.0230 (4)	−0.0075 (4)	−0.0101 (4)	−0.0023 (4)
O3	0.0373 (5)	0.0201 (4)	0.0304 (5)	−0.0067 (4)	−0.0098 (4)	−0.0040 (4)
O4	0.0360 (5)	0.0177 (4)	0.0330 (5)	−0.0036 (4)	−0.0161 (4)	−0.0018 (4)
N1	0.0269 (5)	0.0189 (5)	0.0222 (5)	−0.0059 (4)	−0.0063 (4)	−0.0012 (4)
C1	0.0247 (6)	0.0257 (6)	0.0212 (6)	−0.0077 (5)	−0.0033 (4)	−0.0044 (5)
C2	0.0211 (5)	0.0241 (6)	0.0208 (6)	−0.0060 (4)	−0.0021 (4)	−0.0022 (5)
C3	0.0243 (6)	0.0344 (7)	0.0223 (6)	−0.0072 (5)	−0.0055 (5)	−0.0027 (5)
C4	0.0223 (6)	0.0315 (7)	0.0254 (6)	−0.0010 (5)	−0.0048 (5)	0.0036 (5)
C5	0.0253 (6)	0.0218 (6)	0.0309 (7)	−0.0016 (5)	−0.0005 (5)	−0.0009 (5)
C6	0.0256 (6)	0.0234 (6)	0.0247 (6)	−0.0059 (5)	−0.0026 (5)	−0.0047 (5)
C7	0.0208 (5)	0.0229 (6)	0.0189 (5)	−0.0050 (4)	−0.0022 (4)	−0.0011 (4)
C8	0.0208 (5)	0.0220 (6)	0.0210 (6)	−0.0063 (4)	−0.0023 (4)	−0.0024 (4)
C9	0.0241 (6)	0.0187 (6)	0.0259 (6)	−0.0033 (4)	−0.0048 (5)	−0.0020 (5)
C10	0.0243 (6)	0.0193 (6)	0.0270 (6)	−0.0047 (4)	−0.0064 (5)	−0.0015 (5)
C11	0.0222 (5)	0.0199 (6)	0.0230 (6)	−0.0051 (4)	−0.0032 (4)	−0.0028 (4)
O5	0.0318 (5)	0.0408 (6)	0.0277 (5)	−0.0105 (4)	−0.0103 (4)	−0.0083 (4)
O6	0.0284 (4)	0.0223 (4)	0.0298 (5)	0.0016 (3)	−0.0047 (4)	−0.0002 (4)
N2	0.0210 (5)	0.0192 (5)	0.0217 (5)	−0.0028 (4)	−0.0030 (4)	−0.0042 (4)
N3	0.0215 (5)	0.0206 (5)	0.0202 (5)	−0.0040 (4)	−0.0048 (4)	−0.0022 (4)
N4	0.0241 (5)	0.0229 (5)	0.0210 (5)	−0.0062 (4)	−0.0053 (4)	−0.0034 (4)
N5	0.0220 (5)	0.0288 (6)	0.0200 (5)	−0.0049 (4)	−0.0064 (4)	0.0009 (4)
C20	0.0344 (7)	0.0211 (6)	0.0321 (7)	−0.0029 (5)	−0.0060 (5)	−0.0094 (5)
C21	0.0206 (5)	0.0211 (6)	0.0208 (6)	−0.0031 (4)	−0.0040 (4)	−0.0028 (4)
C22	0.0179 (5)	0.0216 (6)	0.0185 (5)	−0.0052 (4)	−0.0016 (4)	−0.0024 (4)
C23	0.0314 (6)	0.0225 (6)	0.0302 (6)	−0.0069 (5)	−0.0068 (5)	−0.0075 (5)
C24	0.0202 (5)	0.0306 (6)	0.0205 (6)	−0.0067 (5)	−0.0032 (4)	−0.0036 (5)
C25	0.0287 (6)	0.0403 (8)	0.0237 (6)	−0.0041 (6)	−0.0105 (5)	0.0046 (6)
C26	0.0180 (5)	0.0243 (6)	0.0213 (6)	−0.0021 (4)	−0.0004 (4)	−0.0013 (5)
C27	0.0190 (5)	0.0208 (6)	0.0208 (6)	−0.0036 (4)	−0.0025 (4)	−0.0032 (4)

O1—C1	1.2106 (15)	O6—C26	1.2265 (15)
O2—C8	1.2132 (14)	N2—C21	1.3446 (15)
O3—C11	1.2066 (15)	N2—C27	1.3867 (15)
O4—C11	1.3312 (14)	N2—C20	1.4604 (16)
O4—H4	0.8400	N3—C21	1.3395 (15)
N1—C8	1.3979 (16)	N3—C22	1.3597 (14)
N1—C1	1.3982 (15)	N4—C22	1.3719 (15)
N1—C9	1.4499 (15)	N4—C24	1.3820 (15)
C1—C2	1.4895 (17)	N4—C23	1.4644 (16)
C2—C3	1.3841 (16)	N5—C24	1.3994 (17)
C2—C7	1.3899 (17)	N5—C26	1.4110 (16)
C3—C4	1.3957 (19)	N5—C25	1.4712 (15)
C3—H3A	0.9500	C20—H20A	0.9800
C4—C5	1.3910 (19)	C20—H20B	0.9800
C4—H4A	0.9500	C20—H20C	0.9800
C5—C6	1.3986 (17)	C21—H21A	0.9500
C5—H5A	0.9500	C22—C27	1.3689 (16)
C6—C7	1.3807 (17)	C23—H23A	0.9800
C6—H6A	0.9500	C23—H23B	0.9800
C7—C8	1.4927 (16)	C23—H23C	0.9800
C9—C10	1.5252 (17)	C25—H25A	0.9800
C9—H9A	0.9900	C25—H25B	0.9800
C9—H9B	0.9900	C25—H25C	0.9800
C10—C11	1.5073 (16)	C25—H25D	0.9800
C10—H10A	0.9900	C25—H25E	0.9800
C10—H10B	0.9900	C25—H25F	0.9800
O5—C24	1.2190 (15)	C26—C27	1.4275 (16)
C11—O4—H4	109.5	C21—N3—C22	104.19 (10)
C8—N1—C1	112.53 (10)	C22—N4—C24	119.59 (10)
C8—N1—C9	123.16 (10)	C22—N4—C23	121.80 (10)
C1—N1—C9	124.26 (10)	C24—N4—C23	118.57 (10)
O1—C1—N1	124.51 (12)	C24—N5—C26	126.81 (10)
O1—C1—C2	130.13 (11)	C24—N5—C25	116.45 (10)
N1—C1—C2	105.36 (10)	C26—N5—C25	116.62 (11)
C3—C2—C7	121.42 (12)	N2—C20—H20A	109.5
C3—C2—C1	130.01 (11)	N2—C20—H20B	109.5
C7—C2—C1	108.56 (10)	H20A—C20—H20B	109.5
C2—C3—C4	117.05 (12)	N2—C20—H20C	109.5
C2—C3—H3A	121.5	H20A—C20—H20C	109.5
C4—C3—H3A	121.5	H20B—C20—H20C	109.5
C5—C4—C3	121.47 (11)	N3—C21—N2	112.65 (10)
C5—C4—H4A	119.3	N3—C21—H21A	123.7
C3—C4—H4A	119.3	N2—C21—H21A	123.7
C4—C5—C6	121.12 (12)	N3—C22—C27	111.37 (10)
C4—C5—H5A	119.4	N3—C22—N4	126.43 (11)
C6—C5—H5A	119.4	C27—C22—N4	122.20 (10)
C7—C6—C5	116.97 (11)	N4—C23—H23A	109.5
C7—C6—H6A	121.5	N4—C23—H23B	109.5
C5—C6—H6A	121.5	H23A—C23—H23B	109.5
C6—C7—C2	121.96 (11)	N4—C23—H23C	109.5
C6—C7—C8	130.04 (11)	H23A—C23—H23C	109.5
C2—C7—C8	107.99 (10)	H23B—C23—H23C	109.5
O2—C8—N1	124.43 (11)	O5—C24—N4	121.12 (12)
O2—C8—C7	130.01 (11)	O5—C24—N5	121.97 (11)
N1—C8—C7	105.56 (10)	N4—C24—N5	116.90 (10)
N1—C9—C10	111.68 (10)	N5—C25—H25A	109.5
N1—C9—H9A	109.3	N5—C25—H25B	109.5
C10—C9—H9A	109.3	H25A—C25—H25B	109.5
N1—C9—H9B	109.3	N5—C25—H25C	109.5
C10—C9—H9B	109.3	H25A—C25—H25C	109.5
H9A—C9—H9B	107.9	H25B—C25—H25C	109.5
C11—C10—C9	109.85 (10)	N5—C25—H25D	109.5
C11—C10—H10A	109.7	N5—C25—H25E	109.5
C9—C10—H10A	109.7	H25D—C25—H25E	109.5
C11—C10—H10B	109.7	N5—C25—H25F	109.5
C9—C10—H10B	109.7	H25D—C25—H25F	109.5
H10A—C10—H10B	108.2	H25E—C25—H25F	109.5
O3—C11—O4	123.34 (11)	O6—C26—N5	121.50 (11)
O3—C11—C10	124.00 (11)	O6—C26—C27	126.91 (12)
O4—C11—C10	112.64 (10)	N5—C26—C27	111.59 (10)
C21—N2—C27	106.39 (10)	C22—C27—N2	105.40 (10)
C21—N2—C20	126.14 (10)	C22—C27—C26	122.76 (11)
C27—N2—C20	127.47 (10)	N2—C27—C26	131.82 (11)
C8—N1—C1—O1	179.26 (12)	C27—N2—C21—N3	0.32 (13)
C9—N1—C1—O1	1.75 (19)	C20—N2—C21—N3	179.91 (11)
C8—N1—C1—C2	−0.27 (13)	C21—N3—C22—C27	0.33 (13)
C9—N1—C1—C2	−177.79 (10)	C21—N3—C22—N4	−179.28 (11)
O1—C1—C2—C3	0.1 (2)	C24—N4—C22—N3	−179.58 (11)
N1—C1—C2—C3	179.57 (12)	C23—N4—C22—N3	−2.06 (18)
O1—C1—C2—C7	−178.84 (13)	C24—N4—C22—C27	0.86 (17)
N1—C1—C2—C7	0.66 (13)	C23—N4—C22—C27	178.37 (11)
C7—C2—C3—C4	0.19 (18)	C22—N4—C24—O5	179.72 (11)
C1—C2—C3—C4	−178.61 (12)	C23—N4—C24—O5	2.12 (18)
C2—C3—C4—C5	0.21 (19)	C22—N4—C24—N5	−1.58 (16)
C3—C4—C5—C6	−0.25 (19)	C23—N4—C24—N5	−179.18 (10)
C4—C5—C6—C7	−0.11 (18)	C26—N5—C24—O5	−177.48 (11)
C5—C6—C7—C2	0.51 (18)	C25—N5—C24—O5	−1.59 (17)
C5—C6—C7—C8	179.56 (12)	C26—N5—C24—N4	3.83 (18)
C3—C2—C7—C6	−0.57 (18)	C25—N5—C24—N4	179.72 (10)
C1—C2—C7—C6	178.46 (11)	C24—N5—C26—O6	175.97 (11)
C3—C2—C7—C8	−179.80 (11)	C25—N5—C26—O6	0.09 (17)
C1—C2—C7—C8	−0.77 (13)	C24—N5—C26—C27	−4.66 (16)
C1—N1—C8—O2	−179.50 (11)	C25—N5—C26—C27	179.45 (10)
C9—N1—C8—O2	−1.95 (18)	N3—C22—C27—N2	−0.15 (13)
C1—N1—C8—C7	−0.18 (13)	N4—C22—C27—N2	179.47 (10)
C9—N1—C8—C7	177.36 (10)	N3—C22—C27—C26	178.33 (10)
C6—C7—C8—O2	0.7 (2)	N4—C22—C27—C26	−2.04 (18)
C2—C7—C8—O2	179.86 (12)	C21—N2—C27—C22	−0.09 (12)
C6—C7—C8—N1	−178.55 (12)	C20—N2—C27—C22	−179.68 (11)
C2—C7—C8—N1	0.60 (13)	C21—N2—C27—C26	−178.38 (12)
C8—N1—C9—C10	103.65 (13)	C20—N2—C27—C26	2.0 (2)
C1—N1—C9—C10	−79.09 (14)	O6—C26—C27—C22	−177.07 (11)
N1—C9—C10—C11	−173.66 (10)	N5—C26—C27—C22	3.61 (16)
C9—C10—C11—O3	−112.03 (13)	O6—C26—C27—N2	1.0 (2)
C9—C10—C11—O4	66.73 (13)	N5—C26—C27—N2	−178.35 (11)
C22—N3—C21—N2	−0.40 (13)

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4···N3i	0.84	1.83	2.6672 (13)	175
C3—H3A···O5ii	0.95	2.26	3.1447 (16)	155
C6—H6A···O3iii	0.95	2.31	3.2283 (16)	162
C20—H20B···O6iv	0.98	2.35	3.2559 (16)	154
C25—H25A···O6	0.98	2.28	2.7244 (18)	107
C25—H25D···O5	0.98	2.26	2.7152 (19)	107

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H4⋯N3i	0.84	1.83	2.6672 (13)	175
C3—H3A⋯O5ii	0.95	2.26	3.1447 (16)	155
C6—H6A⋯O3iii	0.95	2.31	3.2283 (16)	162
C20—H20B⋯O6iv	0.98	2.35	3.2559 (16)	154

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