5-(6-Amino-1,3-dimethyl-2,4-dioxo-1,2,3,4-tetra­hydropyrimidin-5-yl)-1,3-dimethyl-1H-chromeno[2,3-d]pyrim­idine-2,4(3H,5H)-dione 3.5-hydrate

Roy, S.; Das, S.

doi:10.1107/S1600536813013986

organic compounds

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ISSN: 2056-9890

Volume 69| Part 6| June 2013| Pages o974-o975

doi:10.1107/S1600536813013986

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5-(6-Amino-1,3-dimethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)-1,3-dimethyl-1H-chromeno[2,3-d]pyrimidine-2,4(3H,5H)-dione 3.5-hydrate

Subhadip Roy ^a and Subrata Das ^a ^*

^aDepartment of Chemistry, National Institute of Technology-Agartala, Pin-799055, Tripura, India
^*Correspondence e-mail: subrataorg@gmail.com

(Received 10 May 2013; accepted 20 May 2013; online 25 May 2013)

The title compound, C₁₉H₁₉N₅O₅·3.5H₂O, crystallizes with 3.5 molecules of water in the asymmetric unit, one of which lies on a mirror plane. One of the water molecules links the molecules, forming centrosymmetric dimers. These dimers are then linked through further N—H⋯O and O—H⋯O hydrogen bonding, leading to the observed three-dimensional structure.

Related literature

Many chromene derivatives occur in natural products, see: Hatakeyama et al. (1988 ). For the biological activity of functionalized chromenes, see: Brooks (1998 ); Valenti et al. (1993 ); Tang et al. (2007 ). For the use of 6-amino-uracil derivatives as precursors in the synthesis of biologically significant fused uracils, see: Shaw (1996 ). The fusion of a chromene unit to the uracil ring is found to increase the biological activity, see: Sabry et al. (2011 ).

Experimental

Crystal data

C₁₉H₁₉N₅O₅·3.5H₂O
M_r = 460.45
Monoclinic, C 2/c
a = 29.993 (4) Å
b = 7.9105 (6) Å
c = 21.458 (3) Å
β = 119.860 (16)°
V = 4415.3 (10) Å³
Z = 8
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 298 K
0.32 × 0.12 × 0.06 mm

Data collection

Oxford Diffraction Xcalibur (Eos, Gemini) diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2007 $[Oxford Diffraction (2007). CrysAlis PRO. Oxford Diffraction Ltd, Abingdon, England.]$ ) T_min = 0.93, T_max = 1.00
9327 measured reflections
4554 independent reflections
2538 reflections with I > 2σ(I)
R_int = 0.069

Refinement

R[F² > 2σ(F²)] = 0.060
wR(F²) = 0.137
S = 0.98
4554 reflections
308 parameters
H-atom parameters constrained
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.25 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N6—H6A⋯O6Wⁱ	0.86	2.18	3.009 (3)	161
N6—H6B⋯O8W	0.86	2.09	2.905 (3)	158
O6W—H6WA⋯O1ⁱⁱ	0.85	2.01	2.830 (3)	162
O6W—H6WB⋯O7W	0.85	2.00	2.835 (3)	167
O7W—H7WA⋯O3ⁱⁱⁱ	0.84	1.94	2.781 (3)	177
O7W—H7WB⋯O2	0.85	1.93	2.773 (3)	170
O8W—H8WA⋯O9W	0.85	1.99	2.838 (4)	177
O8W—H8WB⋯O6W^iv	0.85	2.01	2.840 (3)	164
O9W—H9W⋯O7W	0.85	1.93	2.772 (3)	170
Symmetry codes: (i) x, y-1, z; (ii) $[-x+{\script{1\over 2}}, -y+{\script{5\over 2}}, -z+1]$ ; (iii) -x+1, -y+2, -z+1; (iv) $[-x+1, y-1, -z+{\script{3\over 2}}]$ .

Data collection: CrysAlis PRO (Oxford Diffraction, 2007 $[Oxford Diffraction (2007). CrysAlis PRO. Oxford Diffraction Ltd, Abingdon, England.]$ ); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: OLEX.SOLVE (Bourhis et al., 2013 ); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008 ); molecular graphics: OLEX2 (Dolomanov et al., 2009 ); software used to prepare material for publication: OLEX2.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536813013986/go2089sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813013986/go2089Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813013986/go2089Isup3.cdx

checkCIF report

Comment top

Functionlized chromenes are of great interest as they have shown to possess antimicrobial, antitumoral, spasmolytic, anticoagulant and antianaphylactic characteristics (Brooks, 1998; Valenti et al., 1993; Tang et al., 2007). Many chromene derivatives also occur in various natural products (Hatakeyama et al., 1988). 6-Amino-uracil derivatives belong to nitrogen-containing heterocycles of pyrimidine family and are used as key precursors for the synthesis of numerous biologically significant fused uracils (Shaw, 1996). The fusion of chromene unit to uracil ring is found to increase biological activity (Sabry et al., 2011). In this context, the synthesis and crystal structure of the title compound are reported.

The molecules are held together through a tightly woven intermolecular hydrogen bonding network, utilizing the three and a half water molecules to establish the three-dimensional structure. The two short hydrogen bonds (D···A = 2.773 (3) and 2.781 (3) Å) show D—H···A angles of 170° and 177° respectively, which are close to the ideal 180°, yield to the formation of 'dimers' (Fig. 2), which are further strongly connected to another dimer (Fig. 3), eventually leading to layers utilizing the many hydrogen bonding interactions available to the system. Finally, these layers are held together by relatively weak C—H···O and N—H···O interactions (Fig. 4 & Fig. 5) so producing a complex three-dimensional structure.

Related literature top

Many chromene derivatives occur in natural products, see: Hatakeyama et al. (1988). For the biological activity of functionlized chromenes, see: Brooks (1998); Valenti et al. (1993); Tang et al. (2007). For the use of 6-amino-uracil derivatives as precusrors in the synthesis of biologically significant fused

uracils, see: Shaw (1996). The fusion of a chromene unit to the uracil ring is found to increase the biological activity, see: Sabry et al. (2011).

Experimental top

Distilled water (30 ml) was added to 6-amino-1,3-dimethyluracil (1 mmol) in a 100 ml round-bottomed flask and the mixture was stirred at room temperature until all the 6-amino- 1,3-dimethyluracil had dissolved. Salicylaldehyde (0.5 mmol) was added drop wise to the 6- amino-1,3-dimethyluracil solution with constant stirring and then after 4 h the product appeared as brown precipitate and stirring was continued for further 3 h so that all of the reactants were converted into product. The brown precipitate was filtered and recrystallized from distilled ethanol to yield white transparent crystals suitable for single-crystal X-ray diffraction (yield 93%; m.p. 520–522 K).

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2007); cell refinement: CrysAlis PRO (Oxford Diffraction, 2007); data reduction: CrysAlis PRO (Oxford Diffraction, 2007); program(s) used to solve structure: OLEX.SOLVE (Bourhis et al., 2013); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

Figures top

	Fig. 1. An overview of the title compound, showing the atom-numbering scheme. Symmetry-generated water molecules are shown in pink. The displacement ellipsoids are shown at the 50% probability level.
	Fig. 2. The dimers formed by the short and geometrically most optimized hydrogen bonds.
	Fig. 3. 'Dimers of dimers' – the basic building blocks of the layers.
	Fig. 4. The layers as seen along the a axis.
	Fig. 5. The same arrangement as in Fig. 4, but rotated by 90⁰ and now seen along the b axis.

5-(6-Amino-1,3-dimethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)-1,3-dimethyl-1H-chromeno[2,3-d]pyrimidine-2,4(3H,5H)-dione 3.5-hydrate top

Crystal data top

C₁₉H₁₉N₅O₅·3.5H₂O	Z = 8
M_r = 460.45	F(000) = 1944
Monoclinic, C2/c	D_x = 1.385 Mg m⁻³
a = 29.993 (4) Å	Mo Kα radiation, λ = 0.71073 Å
b = 7.9105 (6) Å	µ = 0.11 mm⁻¹
c = 21.458 (3) Å	T = 298 K
β = 119.860 (16)°	Block, clear colourless
V = 4415.3 (10) Å³	0.32 × 0.12 × 0.06 mm

Data collection top

Oxford Diffraction Xcalibur (Eos, Gemini) diffractometer	4554 independent reflections
Radiation source: Enhance (Mo) X-ray Source	2538 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.069
Detector resolution: 16.1511 pixels mm^-1	θ_max = 26.5°, θ_min = 2.8°
ω scans	h = −37→36
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2007)	k = −9→5
T_min = 0.93, T_max = 1.00	l = −26→26
9327 measured reflections

Refinement top

Refinement on F²	H-atom parameters constrained
Least-squares matrix: full	w = 1/[σ²(F_o²) + (0.037P)²] where P = (F_o² + 2F_c²)/3
R[F² > 2σ(F²)] = 0.060	(Δ/σ)_max = 0.001
wR(F²) = 0.137	Δρ_max = 0.24 e Å⁻³
S = 0.98	Δρ_min = −0.25 e Å⁻³
4554 reflections	Extinction correction: SHELXL2013 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
308 parameters	Extinction coefficient: 0.0029 (2)
0 restraints

Crystal data top

C₁₉H₁₉N₅O₅·3.5H₂O	V = 4415.3 (10) Å³
M_r = 460.45	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 29.993 (4) Å	µ = 0.11 mm⁻¹
b = 7.9105 (6) Å	T = 298 K
c = 21.458 (3) Å	0.32 × 0.12 × 0.06 mm
β = 119.860 (16)°

Data collection top

Oxford Diffraction Xcalibur (Eos, Gemini) diffractometer	4554 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2007)	2538 reflections with I > 2σ(I)
T_min = 0.93, T_max = 1.00	R_int = 0.069
9327 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.060	0 restraints
wR(F²) = 0.137	H-atom parameters constrained
S = 0.98	Δρ_max = 0.24 e Å⁻³
4554 reflections	Δρ_min = −0.25 e Å⁻³
308 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O1	0.20391 (8)	1.0426 (2)	0.41093 (10)	0.0553 (6)
O2	0.36262 (7)	0.8244 (2)	0.56168 (9)	0.0444 (5)
O3	0.51160 (8)	0.8412 (3)	0.44642 (10)	0.0579 (6)
O4	0.34405 (7)	0.6704 (2)	0.34016 (8)	0.0442 (5)
O5	0.24740 (6)	0.5527 (2)	0.34356 (8)	0.0378 (5)
N1	0.28226 (8)	0.9305 (3)	0.48757 (10)	0.0350 (5)
N2	0.22732 (8)	0.8001 (3)	0.37727 (10)	0.0374 (6)
N3	0.42861 (9)	0.7489 (3)	0.39256 (11)	0.0399 (6)
N4	0.48358 (8)	0.7140 (3)	0.51612 (10)	0.0359 (6)
N6	0.45814 (8)	0.5830 (3)	0.58939 (10)	0.0469 (7)
H6A	0.4358	0.5337	0.5972	0.056*
H6B	0.4891	0.5975	0.6240	0.056*
C1	0.23592 (11)	0.9317 (4)	0.42411 (14)	0.0398 (7)
C2	0.26390 (10)	0.6756 (3)	0.39378 (12)	0.0316 (6)
C3	0.31020 (9)	0.6787 (3)	0.45432 (12)	0.0289 (6)
C4	0.32143 (10)	0.8121 (3)	0.50451 (12)	0.0323 (6)
C5	0.47635 (11)	0.7709 (3)	0.45087 (14)	0.0394 (7)
C6	0.44477 (10)	0.6371 (3)	0.52362 (12)	0.0307 (6)
C7	0.39607 (9)	0.6201 (3)	0.46424 (11)	0.0284 (6)
C8	0.38635 (11)	0.6784 (3)	0.39612 (12)	0.0338 (6)
C9	0.35107 (9)	0.5470 (3)	0.46939 (11)	0.0297 (6)
H9	0.3645	0.5081	0.5189	0.036*
C10	0.32640 (10)	0.3965 (3)	0.42059 (12)	0.0294 (6)
C11	0.27754 (10)	0.4047 (3)	0.36074 (12)	0.0307 (6)
C12	0.25456 (11)	0.2707 (3)	0.31460 (13)	0.0418 (7)
H12	0.2217	0.2811	0.2751	0.050*
C13	0.28154 (13)	0.1200 (4)	0.32827 (14)	0.0484 (8)
H13	0.2669	0.0284	0.2975	0.058*
C14	0.33003 (12)	0.1059 (4)	0.38743 (15)	0.0466 (8)
H14	0.3480	0.0047	0.3966	0.056*
C15	0.35207 (11)	0.2422 (3)	0.43328 (13)	0.0384 (7)
H15	0.3846	0.2306	0.4733	0.046*
C16	0.17779 (11)	0.7988 (4)	0.30914 (13)	0.0573 (9)
H16A	0.1795	0.7193	0.2766	0.086*
H16B	0.1709	0.9096	0.2881	0.086*
H16C	0.1508	0.7667	0.3184	0.086*
C17	0.29347 (11)	1.0725 (3)	0.53773 (14)	0.0498 (8)
H17A	0.3180	1.0370	0.5856	0.075*
H17B	0.2623	1.1077	0.5363	0.075*
H17C	0.3074	1.1651	0.5240	0.075*
C18	0.53408 (11)	0.7462 (4)	0.57937 (14)	0.0517 (8)
H18A	0.5296	0.8003	0.6159	0.078*
H18B	0.5538	0.8184	0.5662	0.078*
H18C	0.5519	0.6410	0.5974	0.078*
C19	0.41982 (13)	0.8013 (4)	0.32181 (13)	0.0627 (10)
H19A	0.3910	0.7404	0.2851	0.094*
H19B	0.4499	0.7775	0.3183	0.094*
H19C	0.4128	0.9204	0.3157	0.094*
O6W	0.40247 (8)	1.3900 (3)	0.65089 (12)	0.0588 (6)
H6WA	0.3707	1.3937	0.6386	0.088*
H6WB	0.4104	1.2891	0.6470	0.088*
O7W	0.43622 (9)	1.0753 (3)	0.62611 (10)	0.0552 (6)
H7WA	0.4531	1.1006	0.6055	0.083*
H7WB	0.4155	0.9949	0.6036	0.083*
O8W	0.54970 (10)	0.6130 (4)	0.72984 (11)	0.0811 (8)
H8WA	0.5350	0.6963	0.7373	0.122*
H8WB	0.5579	0.5401	0.7631	0.122*
O9W	0.5000	0.8957 (5)	0.7500	0.1228 (18)
H9W	0.4827	0.9612	0.7146	0.184*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0445 (13)	0.0462 (12)	0.0788 (14)	0.0148 (11)	0.0333 (12)	0.0016 (11)
O2	0.0366 (12)	0.0490 (12)	0.0398 (10)	−0.0016 (10)	0.0131 (9)	−0.0123 (9)
O3	0.0455 (14)	0.0749 (15)	0.0645 (13)	−0.0121 (12)	0.0357 (11)	0.0036 (11)
O4	0.0348 (12)	0.0556 (12)	0.0329 (9)	−0.0022 (10)	0.0098 (9)	0.0056 (9)
O5	0.0291 (10)	0.0419 (11)	0.0321 (9)	−0.0001 (9)	0.0075 (8)	−0.0069 (8)
N1	0.0314 (13)	0.0298 (12)	0.0480 (12)	0.0017 (11)	0.0229 (11)	−0.0050 (10)
N2	0.0227 (12)	0.0441 (14)	0.0399 (12)	0.0061 (11)	0.0114 (10)	−0.0007 (11)
N3	0.0388 (15)	0.0482 (14)	0.0377 (12)	−0.0051 (12)	0.0229 (11)	0.0031 (11)
N4	0.0251 (13)	0.0444 (13)	0.0371 (11)	0.0000 (11)	0.0146 (10)	0.0003 (10)
N6	0.0248 (13)	0.0726 (17)	0.0309 (11)	−0.0112 (13)	0.0044 (10)	0.0060 (11)
C1	0.0354 (16)	0.0398 (16)	0.0509 (16)	0.0040 (14)	0.0266 (14)	0.0040 (14)
C2	0.0241 (14)	0.0342 (14)	0.0349 (13)	−0.0023 (12)	0.0134 (12)	−0.0023 (11)
C3	0.0232 (14)	0.0298 (14)	0.0326 (12)	−0.0032 (11)	0.0131 (11)	−0.0041 (11)
C4	0.0302 (15)	0.0366 (15)	0.0333 (13)	−0.0059 (13)	0.0181 (12)	−0.0033 (11)
C5	0.0329 (17)	0.0404 (16)	0.0521 (17)	0.0039 (14)	0.0268 (14)	0.0025 (14)
C6	0.0263 (14)	0.0345 (14)	0.0327 (13)	0.0023 (12)	0.0158 (11)	−0.0005 (12)
C7	0.0222 (14)	0.0303 (14)	0.0312 (12)	0.0054 (11)	0.0121 (11)	0.0025 (11)
C8	0.0340 (16)	0.0348 (15)	0.0313 (13)	0.0019 (13)	0.0153 (12)	−0.0010 (11)
C9	0.0246 (14)	0.0342 (14)	0.0260 (12)	−0.0001 (12)	0.0094 (11)	−0.0015 (11)
C10	0.0302 (15)	0.0307 (14)	0.0333 (13)	−0.0038 (12)	0.0204 (12)	−0.0032 (11)
C11	0.0312 (15)	0.0337 (14)	0.0284 (12)	0.0008 (12)	0.0157 (11)	−0.0024 (11)
C12	0.0442 (18)	0.0456 (17)	0.0338 (14)	−0.0154 (15)	0.0182 (13)	−0.0104 (13)
C13	0.065 (2)	0.0394 (17)	0.0512 (17)	−0.0101 (17)	0.0370 (17)	−0.0134 (14)
C14	0.060 (2)	0.0339 (16)	0.0600 (18)	−0.0009 (15)	0.0404 (17)	−0.0045 (14)
C15	0.0395 (17)	0.0361 (15)	0.0443 (15)	0.0054 (14)	0.0243 (13)	0.0037 (13)
C16	0.0357 (19)	0.069 (2)	0.0505 (17)	0.0128 (17)	0.0093 (15)	−0.0031 (16)
C17	0.057 (2)	0.0424 (17)	0.0625 (18)	−0.0016 (16)	0.0394 (17)	−0.0147 (15)
C18	0.0275 (16)	0.069 (2)	0.0514 (17)	−0.0142 (16)	0.0140 (14)	−0.0073 (16)
C19	0.073 (3)	0.080 (2)	0.0452 (16)	−0.018 (2)	0.0366 (17)	0.0045 (17)
O6W	0.0444 (14)	0.0660 (15)	0.0617 (13)	−0.0016 (12)	0.0231 (12)	−0.0009 (12)
O7W	0.0469 (15)	0.0627 (15)	0.0571 (12)	−0.0127 (12)	0.0267 (11)	−0.0025 (11)
O8W	0.0576 (17)	0.114 (2)	0.0506 (13)	0.0053 (16)	0.0110 (12)	0.0133 (14)
O9W	0.157 (4)	0.076 (3)	0.060 (2)	0.000	−0.002 (2)	0.000

Geometric parameters (Å, º) top

O1—C1	1.225 (3)	C10—C11	1.388 (3)
O2—C4	1.238 (3)	C10—C15	1.396 (3)
O3—C5	1.240 (3)	C11—C12	1.378 (3)
O4—C8	1.240 (3)	C12—H12	0.9300
O5—C2	1.349 (3)	C12—C13	1.388 (4)
O5—C11	1.411 (3)	C13—H13	0.9300
N1—C1	1.379 (3)	C13—C14	1.379 (4)
N1—C4	1.401 (3)	C14—H14	0.9300
N1—C17	1.474 (3)	C14—C15	1.385 (3)
N2—C1	1.379 (3)	C15—H15	0.9300
N2—C2	1.383 (3)	C16—H16A	0.9600
N2—C16	1.477 (3)	C16—H16B	0.9600
N3—C5	1.365 (3)	C16—H16C	0.9600
N3—C8	1.421 (3)	C17—H17A	0.9600
N3—C19	1.465 (3)	C17—H17B	0.9600
N4—C5	1.381 (3)	C17—H17C	0.9600
N4—C6	1.392 (3)	C18—H18A	0.9600
N4—C18	1.468 (3)	C18—H18B	0.9600
N6—H6A	0.8600	C18—H18C	0.9600
N6—H6B	0.8600	C19—H19A	0.9600
N6—C6	1.331 (3)	C19—H19B	0.9600
C2—C3	1.349 (3)	C19—H19C	0.9600
C3—C4	1.424 (3)	O6W—H6WA	0.8524
C3—C9	1.516 (3)	O6W—H6WB	0.8486
C6—C7	1.386 (3)	O7W—H7WA	0.8449
C7—C8	1.418 (3)	O7W—H7WB	0.8516
C7—C9	1.522 (3)	O8W—H8WA	0.8524
C9—H9	0.9800	O8W—H8WB	0.8519
C9—C10	1.513 (3)	O9W—H9W	0.8500

C2—O5—C11	117.17 (18)	C11—C10—C9	122.1 (2)
C1—N1—C4	124.3 (2)	C11—C10—C15	116.6 (2)
C1—N1—C17	117.8 (2)	C15—C10—C9	121.4 (2)
C4—N1—C17	117.6 (2)	C10—C11—O5	121.6 (2)
C1—N2—C2	121.0 (2)	C12—C11—O5	115.1 (2)
C1—N2—C16	117.2 (2)	C12—C11—C10	123.3 (2)
C2—N2—C16	121.8 (2)	C11—C12—H12	120.7
C5—N3—C8	123.9 (2)	C11—C12—C13	118.6 (3)
C5—N3—C19	118.6 (2)	C13—C12—H12	120.7
C8—N3—C19	117.5 (2)	C12—C13—H13	120.0
C5—N4—C6	122.8 (2)	C14—C13—C12	120.0 (3)
C5—N4—C18	116.7 (2)	C14—C13—H13	120.0
C6—N4—C18	120.4 (2)	C13—C14—H14	119.9
H6A—N6—H6B	120.0	C13—C14—C15	120.2 (3)
C6—N6—H6A	120.0	C15—C14—H14	119.9
C6—N6—H6B	120.0	C10—C15—H15	119.3
O1—C1—N1	121.4 (3)	C14—C15—C10	121.3 (3)
O1—C1—N2	122.1 (3)	C14—C15—H15	119.3
N1—C1—N2	116.4 (2)	N2—C16—H16A	109.5
O5—C2—N2	112.3 (2)	N2—C16—H16B	109.5
O5—C2—C3	125.1 (2)	N2—C16—H16C	109.5
C3—C2—N2	122.6 (2)	H16A—C16—H16B	109.5
C2—C3—C4	119.0 (2)	H16A—C16—H16C	109.5
C2—C3—C9	121.9 (2)	H16B—C16—H16C	109.5
C4—C3—C9	119.1 (2)	N1—C17—H17A	109.5
O2—C4—N1	119.9 (2)	N1—C17—H17B	109.5
O2—C4—C3	123.5 (2)	N1—C17—H17C	109.5
N1—C4—C3	116.6 (2)	H17A—C17—H17B	109.5
O3—C5—N3	122.2 (2)	H17A—C17—H17C	109.5
O3—C5—N4	121.0 (3)	H17B—C17—H17C	109.5
N3—C5—N4	116.8 (2)	N4—C18—H18A	109.5
N6—C6—N4	115.8 (2)	N4—C18—H18B	109.5
N6—C6—C7	124.5 (2)	N4—C18—H18C	109.5
C7—C6—N4	119.7 (2)	H18A—C18—H18B	109.5
C6—C7—C8	119.9 (2)	H18A—C18—H18C	109.5
C6—C7—C9	122.5 (2)	H18B—C18—H18C	109.5
C8—C7—C9	117.6 (2)	N3—C19—H19A	109.5
O4—C8—N3	118.5 (2)	N3—C19—H19B	109.5
O4—C8—C7	124.6 (3)	N3—C19—H19C	109.5
C7—C8—N3	116.9 (2)	H19A—C19—H19B	109.5
C3—C9—C7	112.1 (2)	H19A—C19—H19C	109.5
C3—C9—H9	107.4	H19B—C19—H19C	109.5
C7—C9—H9	107.4	H6WA—O6W—H6WB	109.1
C10—C9—C3	109.15 (19)	H7WA—O7W—H7WB	109.8
C10—C9—C7	113.24 (19)	H8WA—O8W—H8WB	109.1
C10—C9—H9	107.4

O5—C2—C3—C4	−176.7 (2)	C7—C9—C10—C15	68.9 (3)
O5—C2—C3—C9	5.0 (4)	C8—N3—C5—O3	−176.0 (2)
O5—C11—C12—C13	−179.4 (2)	C8—N3—C5—N4	2.7 (4)
N2—C2—C3—C4	2.1 (4)	C8—C7—C9—C3	−65.0 (3)
N2—C2—C3—C9	−176.2 (2)	C8—C7—C9—C10	59.0 (3)
N4—C6—C7—C8	1.1 (4)	C9—C3—C4—O2	−2.4 (4)
N4—C6—C7—C9	−176.3 (2)	C9—C3—C4—N1	179.7 (2)
N6—C6—C7—C8	−178.3 (2)	C9—C7—C8—O4	−1.7 (4)
N6—C6—C7—C9	4.3 (4)	C9—C7—C8—N3	179.0 (2)
C1—N1—C4—O2	177.3 (2)	C9—C10—C11—O5	−2.3 (4)
C1—N1—C4—C3	−4.7 (4)	C9—C10—C11—C12	178.7 (2)
C1—N2—C2—O5	176.3 (2)	C9—C10—C15—C14	−178.2 (2)
C1—N2—C2—C3	−2.6 (4)	C10—C11—C12—C13	−0.2 (4)
C2—O5—C11—C10	−11.2 (3)	C11—O5—C2—N2	−168.9 (2)
C2—O5—C11—C12	167.9 (2)	C11—O5—C2—C3	10.0 (4)
C2—N2—C1—O1	−179.3 (2)	C11—C10—C15—C14	1.2 (4)
C2—N2—C1—N1	−0.5 (4)	C11—C12—C13—C14	0.7 (4)
C2—C3—C4—O2	179.3 (2)	C12—C13—C14—C15	−0.2 (4)
C2—C3—C4—N1	1.4 (4)	C13—C14—C15—C10	−0.8 (4)
C2—C3—C9—C7	109.6 (3)	C15—C10—C11—O5	178.3 (2)
C2—C3—C9—C10	−16.7 (3)	C15—C10—C11—C12	−0.7 (4)
C3—C9—C10—C11	15.2 (3)	C16—N2—C1—O1	0.9 (4)
C3—C9—C10—C15	−165.5 (2)	C16—N2—C1—N1	179.7 (2)
C4—N1—C1—O1	−176.9 (2)	C16—N2—C2—O5	−4.0 (3)
C4—N1—C1—N2	4.3 (4)	C16—N2—C2—C3	177.1 (2)
C4—C3—C9—C7	−68.7 (3)	C17—N1—C1—O1	−3.3 (4)
C4—C3—C9—C10	165.0 (2)	C17—N1—C1—N2	177.9 (2)
C5—N3—C8—O4	177.1 (2)	C17—N1—C4—O2	3.7 (4)
C5—N3—C8—C7	−3.5 (4)	C17—N1—C4—C3	−178.4 (2)
C5—N4—C6—N6	177.5 (2)	C18—N4—C5—O3	2.0 (4)
C5—N4—C6—C7	−2.0 (4)	C18—N4—C5—N3	−176.7 (2)
C6—N4—C5—O3	178.9 (3)	C18—N4—C6—N6	−5.8 (4)
C6—N4—C5—N3	0.1 (4)	C18—N4—C6—C7	174.7 (2)
C6—C7—C8—O4	−179.2 (2)	C19—N3—C5—O3	3.7 (4)
C6—C7—C8—N3	1.5 (3)	C19—N3—C5—N4	−177.6 (2)
C6—C7—C9—C3	112.4 (3)	C19—N3—C8—O4	−2.5 (4)
C6—C7—C9—C10	−123.6 (2)	C19—N3—C8—C7	176.8 (2)
C7—C9—C10—C11	−110.4 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N6—H6A···O6Wⁱ	0.86	2.18	3.009 (3)	161
N6—H6B···O8W	0.86	2.09	2.905 (3)	158
O6W—H6WA···O1ⁱⁱ	0.85	2.01	2.830 (3)	162
O6W—H6WB···O7W	0.85	2.00	2.835 (3)	167
O7W—H7WA···O3ⁱⁱⁱ	0.84	1.94	2.781 (3)	177
O7W—H7WB···O2	0.85	1.93	2.773 (3)	170
O8W—H8WA···O9W	0.85	1.99	2.838 (4)	177
O8W—H8WB···O6W^iv	0.85	2.01	2.840 (3)	164
O9W—H9W···O7W	0.85	1.93	2.772 (3)	170

Symmetry codes: (i) x, y−1, z; (ii) −x+1/2, −y+5/2, −z+1; (iii) −x+1, −y+2, −z+1; (iv) −x+1, y−1, −z+3/2.

Experimental details

Crystal data
Chemical formula	C₁₉H₁₉N₅O₅·3.5H₂O
M_r	460.45
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	298
a, b, c (Å)	29.993 (4), 7.9105 (6), 21.458 (3)
β (°)	119.860 (16)
V (Å³)	4415.3 (10)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.32 × 0.12 × 0.06

Data collection
Diffractometer	Oxford Diffraction Xcalibur (Eos, Gemini) diffractometer
Absorption correction	Multi-scan (CrysAlis PRO; Oxford Diffraction, 2007)
T_min, T_max	0.93, 1.00
No. of measured, independent and observed [I > 2σ(I)] reflections	9327, 4554, 2538
R_int	0.069
(sin θ/λ)_max (Å⁻¹)	0.628

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.060, 0.137, 0.98
No. of reflections	4554
No. of parameters	308
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.24, −0.25

Computer programs: CrysAlis PRO (Oxford Diffraction, 2007), OLEX.SOLVE (Bourhis et al., 2013), SHELXL2013 (Sheldrick, 2008), OLEX2 (Dolomanov et al., 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N6—H6A···O6Wⁱ	0.86	2.18	3.009 (3)	161
N6—H6B···O8W	0.86	2.09	2.905 (3)	158
O6W—H6WA···O1ⁱⁱ	0.85	2.01	2.830 (3)	162
O6W—H6WB···O7W	0.85	2.00	2.835 (3)	167
O7W—H7WA···O3ⁱⁱⁱ	0.84	1.94	2.781 (3)	177
O7W—H7WB···O2	0.85	1.93	2.773 (3)	170
O8W—H8WA···O9W	0.85	1.99	2.838 (4)	177
O8W—H8WB···O6W^iv	0.85	2.01	2.840 (3)	164
O9W—H9W···O7W	0.85	1.93	2.772 (3)	170

Symmetry codes: (i) x, y−1, z; (ii) −x+1/2, −y+5/2, −z+1; (iii) −x+1, −y+2, −z+1; (iv) −x+1, y−1, −z+3/2.

Acknowledgements

Financial assistance from the Department of Biotechnology (DBT), Government of India (vide sanction NO BCIL/NER-BPMC/2012.1549) is gratefully acknowledged.

References

Bourhis, L. J., Dolomanov, O. V., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2013). In preparation. Google Scholar
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Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339–341. Web of Science CrossRef CAS IUCr Journals Google Scholar
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Sabry, N. M., Mohamed, H. M., Khattab, E. S. A. E. H., Motlaq, S. S. & El-Agrody, A. M. (2011). Eur. J. Med. Chem. 46, 765–772. Web of Science CrossRef CAS PubMed Google Scholar
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Volume 69| Part 6| June 2013| Pages o974-o975

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

5-(6-Amino-1,3-di­methyl-2,4-dioxo-1,2,3,4-tetra­hydropyrimidin-5-yl)-1,3-di­methyl-1H-chromeno[2,3-d]pyrim­idine-2,4(3H,5H)-dione 3.5-hydrate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

5-(6-Amino-1,3-dimethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)-1,3-dimethyl-1H-chromeno[2,3-d]pyrimidine-2,4(3H,5H)-dione 3.5-hydrate