Caffeine–N-phthaloyl-β-alanine (1/1)

Bhatti, M.H.; Yunus, U.; Shah, S.R.; Flörke, U.

doi:10.1107/S1600536812022696

organic compounds

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ISSN: 2056-9890

Volume 68| Part 6| June 2012| Page o1888

doi:10.1107/S1600536812022696

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Caffeine–N-phthaloyl-β-alanine (1/1)

Moazzam H. Bhatti,^a ^* Uzma Yunus,^a Syed Raza Shah ^a and Ulrich Flörke ^b

^aDepartment of Chemistry, Allama Iqbal Open University, Islamabad, Pakistan, and ^bAnorganische und Analytische Chemie, Fakultät für Naturwissenschaften, Universität Paderborn, Warburgerstrasse 100, D-33098 Paderborn, Germany
^*Correspondence e-mail: moazzamhussain_b@yahoo.com

(Received 7 May 2012; accepted 18 May 2012; online 26 May 2012)

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)], C₈H₁₀N₄O₂·C₁₁H₉NO₄, 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 molecules 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 molecules are linked via an O—H⋯N hydrogen bond involving the intact carboxylic acid (COOH) group. The crystal structure is consolidated by C—H⋯O interactions. The H atoms of a methyl group of the caffeine molecule 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_r = 413.39
Triclinic, $[P \overline 1]$
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[F² > 2σ(F²)] = 0.039
wR(F²) = 0.106
S = 1.03
4378 reflections
277 parameters
H-atom parameters constrained
Δρ_max = 0.26 e Å⁻³
Δρ_min = −0.26 e Å⁻³

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⋯O6^iv	0.98	2.35	3.2559 (16)	154
Symmetry codes: (i) -x+1, -y, -z+2; (ii) -x, -y+1, -z+1; (iii) x, y+1, z; (iv) -x, -y+1, -z+2.

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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812022696/pv2544sup1.cif

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

Supporting information file. DOI: 10.1107/S1600536812022696/pv2544Isup3.cml

checkCIF report

Comment top

Previously we have reported the synthesis and crystal structure of a 1:1 adduct of N-phthaloylglycine with caffeine (Bhatti et al., 2011). Now we have synthesized a 1:1 adduct of N-phthaloyl-β-alanine with caffeine and determined its crystal structure which is reported in this article.

The asymmetric unit of the title adduct is presented in Figure 1. The phthalimide and purine rings in the N-phthaloyl-β-alanine and caffeine molecules are essentailly planar with rms deviations of fitted atoms 0.0078 and 0.0118 Å, respectively; the dihedral angle between the mean-planes of these rings is 5.59 (5)°. The dihedral angle between phthlimide and propanoic acid is 6.5 (1)° slightly less than reported value of N-phthaloyl-β-alanine (Feeder & Jones, 1996). The carbon oxygen distance in the carboxylic acid group (COOH) show typical double and single bond values [C11—O3 = 1.2066 (15) Å and C11—O4 = 1.3312 (14) Å, respectively)], indicating intact protonation of carboxylic acid group. This is further strengthened by intermolecular O4—H4···N3 hydrogen bonding which link the two molecules (Fig. 2). The crystal structure is further consolidated by C—H···O type intermolecular interactions (Table 1).

Related literature top

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

Experimental top

A mixture of N-phthaloyl-β-alanine (0.01 mol) and caffeine (0.01 mol) was heated in water (100 ml) for 2 h. The hot solution was filtered and the filtrate was set aside for one week. Colourless needle like crystals were obtained suitable for X-ray analysis.

Computing details top

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

Figures top

	Fig. 1. The molecular structure of the title adduct with the atom numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. H atoms are presented as small spheres of arbitrary radius.
	Fig. 2. A view of the O—H···N hydrogen bonds (dotted lines) in the crystal structure of the title compound. H atoms non-participating in hydrogen- bonding were omitted for clarity.

3-(1,3-dioxoisoindolin-2-yl)propanoic acid– 1,3,7-trimethyl-1H-purine-2,6(3H,7H)-dione (1/1) top

Crystal data top

C₈H₁₀N₄O₂·C₁₁H₉NO₄	Z = 2
M_r = 413.39	F(000) = 432
Triclinic, P1	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0581P)² + 0.1919P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max < 0.001
4378 reflections	Δρ_max = 0.26 e Å⁻³
277 parameters	Δρ_min = −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)

Crystal data top

C₈H₁₀N₄O₂·C₁₁H₉NO₄	γ = 72.865 (4)°
M_r = 413.39	V = 924.6 (3) Å³
Triclinic, P1	Z = 2
a = 8.3411 (17) Å	Mo Kα radiation
b = 9.0638 (18) Å	µ = 0.11 mm⁻¹
c = 13.162 (3) Å	T = 130 K
α = 77.105 (4)°	0.42 × 0.40 × 0.35 mm
β = 82.394 (4)°

Data collection top

Bruker SMART APEX diffractometer	4378 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	3752 reflections with I > 2σ(I)
T_min = 0.954, T_max = 0.962	R_int = 0.022
8826 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	0 restraints
wR(F²) = 0.106	H-atom parameters constrained
S = 1.03	Δρ_max = 0.26 e Å⁻³
4378 reflections	Δρ_min = −0.26 e Å⁻³
277 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	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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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···O6^iv	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

Symmetry codes: (i) −x+1, −y, −z+2; (ii) −x, −y+1, −z+1; (iii) x, y+1, z; (iv) −x, −y+1, −z+2.

Experimental details

Crystal data
Chemical formula	C₈H₁₀N₄O₂·C₁₁H₉NO₄
M_r	413.39
Crystal system, space group	Triclinic, P1
Temperature (K)	130
a, b, c (Å)	8.3411 (17), 9.0638 (18), 13.162 (3)
α, β, γ (°)	77.105 (4), 82.394 (4), 72.865 (4)
V (Å³)	924.6 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.42 × 0.40 × 0.35

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2004)
T_min, T_max	0.954, 0.962
No. of measured, independent and observed [I > 2σ(I)] reflections	8826, 4378, 3752
R_int	0.022
(sin θ/λ)_max (Å⁻¹)	0.658

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.106, 1.03
No. of reflections	4378
No. of parameters	277
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.26, −0.26

Computer programs: SMART (Bruker, 2002), SAINT (Bruker, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008) and local programs.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4···N3ⁱ	0.84	1.83	2.6672 (13)	175.3
C3—H3A···O5ⁱⁱ	0.95	2.26	3.1447 (16)	155.1
C6—H6A···O3ⁱⁱⁱ	0.95	2.31	3.2283 (16)	162.3
C20—H20B···O6^iv	0.98	2.35	3.2559 (16)	154.2

Symmetry codes: (i) −x+1, −y, −z+2; (ii) −x, −y+1, −z+1; (iii) x, y+1, z; (iv) −x, −y+1, −z+2.

Acknowledgements

The authors gratefully acknowledge Allama Iqbal Open University, Islamabad, Pakistan, for providing research facilities.

References

Bhatti, M. H., Yunus, U., Saeed, S., Shah, S. R. & Wong, W.-T. (2011). Acta Cryst. E67, o2240. Web of Science CSD CrossRef IUCr Journals Google Scholar
Bruker (2002). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Feeder, N. & Jones, W. (1996). Acta Cryst. C52, 913–919. CSD CrossRef CAS Web of Science IUCr Journals Google Scholar
Sheldrick, G. M. (2004). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar