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In the title compound, C14H19N5O4·H2O, the 3,4-dihydro­pteridine ring system deviates sigificantly from planarity, the dihedral angle between the mean planes of the two rings being 3.93 (9)°. Intra­molecular N—H...O hydrogen bonding generates an S(6) ring motif. The water mol­ecule forms O—H...O and O—H...N intra­molecular hydrogen bonds with the substituted pteridine mol­ecule. In the crystal structure, the substituted pteridine mol­ecules are linked by N—H...N hydrogen bonds into chains running along the c direction. These chains are further connected to the water mol­ecules by N—H...O, O—H...O and O—H...N hydrogen bonds to form two-dimensional networks parallel to the bc plane. The crystal structure is stabilized by intra- and inter­molecular N—H...O, N—H...N, O—H...O and O—H...N hydrogen bonds, together with weak C—H...O and C—H...N intra- and inter­molecular inter­actions. C—H...π inter­actions are also observed.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807047940/kj2066sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807047940/kj2066Isup2.hkl
Contains datablock I

CCDC reference: 669132

Key indicators

  • Single-crystal X-ray study
  • T = 100 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.061
  • wR factor = 0.166
  • Data-to-parameter ratio = 20.5

checkCIF/PLATON results

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Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 2
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Comment top

6-Formylpterin is a useful precursor to the nutrient cofactor folic acid, anticancer drug methotrexate (Piper & Montgomery, 1977) and related pteridines like biopterin, neopterin, monapterin, umanopterin as well as precursor Z of molybdenum cofactor or Moco (Pateman et al., 1964; Hille, 1996). These naturally occurring pteridine derivatives are mostly found in human urine and plasma, toad skins, germinating potatoes and various micro-organisms. All compounds of these heterocyclic ring systems found in nature so far, are derivatives of pterin and lumazine carrying different substituents in the 6- and/or 7- positions. One interesting aspect of the pterin system besides its biological importance is that pterins are fluorescent and thus fluorescence assay makes them detectable in biological systems even in trace amounts. We report here the hydrogen-bonding network in the crystal structure of the title compound, as an example of a 7-substituted soluble pterin derivative. We have previously reported the crystal structures of pivaloyl halopterins (Goswami et al., 2000; Shanmuga Sundara Raj et al., 2000), as part of our research program on solubilizing pterins and establish their X-ray structures to investigate their supramolecular network. The first general and unequivocal multistep 7-formylpterin dimethyl acetal was elegantly synthesized by Taylor (Taylor & Dumas, 1981).

In the molecules of the title compound (Fig. 1), the 3,4-dihydropteridine ring (N2–N5/C1–C6) deviates significantly from planarity with the largest deviations found for atoms N2 and N5 [0.0824 (17) and -0.0472 (16) Å, respectively], and the total puckering parameter Q = 0.144 (2) Å (Cremer & Pople, 1975). The dihedral angle between the mean planes of the two rings in the molecular structure is 3.93 (9)°. The 2,2-dimethylpropionamide substituent (O1/N1/C7–C11) is attached at atom C6, the dihedral angle between the mean plane of O1/N1/C6/C7/C8 group and the attached ring is 23.80 (9)°. The orientation of the two dimethoxymethyl groups can be indicated by the torsion angles C13—O3—C12—C4 = 168.57 (16)° and C14—O4—C12—C4 = 57.4 (2)°. The intramolecular N—H···O hydrogen bond generates an S(6) ring motif (Bernstein et al., 1995). The water molecule forms intramolecular O—H···O and O—H···N hydrogen bonds with the 3,4-dihydro-pteridine (Table 1). In the crystal (Fig. 2), the substituted-pteridine molecules are linked by N—H···N hydrogen bonds (N2—H1N2···N3) into chains running along the c direction. These chains are further connected to the water molecules by N—H···O, O—H···O and O—H···N hydrogen bonds to form two-dimemsional networks parallel to the bc plane. The crystal is stabilized by intra- and intermolecular N—H···O, N—H···N, O—H···O and O—H···N hydrogen bonds together with weak C—H···O and C—H···N intra- and intermolecular interactions. C—H···π interactions further stabilized the crystal (Table 1); Cg1 and Cg2 are the centroids of the C1/C2/C5/N3/C6/N2 and N5/C3/C4/N4/C5/C2 rings, respectively.

Related literature top

For related literature on the chemistry and applications of pteridine derivatives, see: e.g. Pateman et al. (1964); Piper & Montgomery (1977); Hille (1996); Taylor & Dumas (1981). For related structures, see: e.g. Goswami et al. (2000); Shanmuga Sundara Raj et al. (2000).

For related literature, see: Bernstein et al. (1995); Cremer & Pople (1975).

Experimental top

7-formylpterin dimethyl acetal (500 mg, 2.11 mmol) and 4-(dimethylamino)-pyridine (50 mg) dissolved in pivalic anhydride (5 ml) were heated at reflux under nitrogen until all of the starting material went into solution (6 h). The excess pivalic anhydride and pivalic acid were removed carefully through short-path distillation under reduced pressure. The brown product was washed well with sodium carbonate followed by water and then extracted with chloroform. The organic layer was evaporated under reduced pressure. The product was purified by silica gel (100–200 mesh) column chromatography eluting with methanol in chloroform (5%) which yielded pure yellow crystalline solid of the title compound (492 mg, 66%, m.p. 396–397 K).

Refinement top

Water H and H atoms attached to N were located in a difference map and their positions and isotropic displacement factors were refined. The remaining H atoms were positioned geometrically and allowed to ride on their parent atoms, with C—H distances in the range 0.93–0.98 Å. The Uiso values were constrained to be 1.5Ueq of the carrier atom for methyl H atoms and 1.2Ueq for the remaining H atoms. A rotating group model was used for the methyl groups.

Structure description top

6-Formylpterin is a useful precursor to the nutrient cofactor folic acid, anticancer drug methotrexate (Piper & Montgomery, 1977) and related pteridines like biopterin, neopterin, monapterin, umanopterin as well as precursor Z of molybdenum cofactor or Moco (Pateman et al., 1964; Hille, 1996). These naturally occurring pteridine derivatives are mostly found in human urine and plasma, toad skins, germinating potatoes and various micro-organisms. All compounds of these heterocyclic ring systems found in nature so far, are derivatives of pterin and lumazine carrying different substituents in the 6- and/or 7- positions. One interesting aspect of the pterin system besides its biological importance is that pterins are fluorescent and thus fluorescence assay makes them detectable in biological systems even in trace amounts. We report here the hydrogen-bonding network in the crystal structure of the title compound, as an example of a 7-substituted soluble pterin derivative. We have previously reported the crystal structures of pivaloyl halopterins (Goswami et al., 2000; Shanmuga Sundara Raj et al., 2000), as part of our research program on solubilizing pterins and establish their X-ray structures to investigate their supramolecular network. The first general and unequivocal multistep 7-formylpterin dimethyl acetal was elegantly synthesized by Taylor (Taylor & Dumas, 1981).

In the molecules of the title compound (Fig. 1), the 3,4-dihydropteridine ring (N2–N5/C1–C6) deviates significantly from planarity with the largest deviations found for atoms N2 and N5 [0.0824 (17) and -0.0472 (16) Å, respectively], and the total puckering parameter Q = 0.144 (2) Å (Cremer & Pople, 1975). The dihedral angle between the mean planes of the two rings in the molecular structure is 3.93 (9)°. The 2,2-dimethylpropionamide substituent (O1/N1/C7–C11) is attached at atom C6, the dihedral angle between the mean plane of O1/N1/C6/C7/C8 group and the attached ring is 23.80 (9)°. The orientation of the two dimethoxymethyl groups can be indicated by the torsion angles C13—O3—C12—C4 = 168.57 (16)° and C14—O4—C12—C4 = 57.4 (2)°. The intramolecular N—H···O hydrogen bond generates an S(6) ring motif (Bernstein et al., 1995). The water molecule forms intramolecular O—H···O and O—H···N hydrogen bonds with the 3,4-dihydro-pteridine (Table 1). In the crystal (Fig. 2), the substituted-pteridine molecules are linked by N—H···N hydrogen bonds (N2—H1N2···N3) into chains running along the c direction. These chains are further connected to the water molecules by N—H···O, O—H···O and O—H···N hydrogen bonds to form two-dimemsional networks parallel to the bc plane. The crystal is stabilized by intra- and intermolecular N—H···O, N—H···N, O—H···O and O—H···N hydrogen bonds together with weak C—H···O and C—H···N intra- and intermolecular interactions. C—H···π interactions further stabilized the crystal (Table 1); Cg1 and Cg2 are the centroids of the C1/C2/C5/N3/C6/N2 and N5/C3/C4/N4/C5/C2 rings, respectively.

For related literature on the chemistry and applications of pteridine derivatives, see: e.g. Pateman et al. (1964); Piper & Montgomery (1977); Hille (1996); Taylor & Dumas (1981). For related structures, see: e.g. Goswami et al. (2000); Shanmuga Sundara Raj et al. (2000).

For related literature, see: Bernstein et al. (1995); Cremer & Pople (1975).

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2 (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 1998); program(s) used to refine structure: SHELXTL (Sheldrick, 1998); molecular graphics: SHELXTL (Sheldrick, 1998); software used to prepare material for publication: SHELXTL (Sheldrick, 1998) and PLATON (Spek, 2003).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound, showing 50% probability displacement ellipsoids and the atomic numbering. Hydrogen bonds were dawn as dash lines.
[Figure 2] Fig. 2. The crystal packing of (I), viewed along the a axis. Hydrogen bonds were drawn as dash lines.
N-(7-Dimethoxymethyl-4-oxo-3,4-dihydropteridin-2-yl)-2,2- dimethylpropionamide monohydrate top
Crystal data top
C14H19N5O4·H2OF(000) = 720
Mr = 339.36Dx = 1.346 Mg m3
Monoclinic, P21/cMelting point = 396–397 K
Hall symbol: -P 2ybcMo Kα radiation, λ = 0.71073 Å
a = 11.9683 (5) ÅCell parameters from 4876 reflections
b = 15.7252 (6) Åθ = 2.6–30.0°
c = 8.9289 (3) ŵ = 0.10 mm1
β = 94.998 (2)°T = 100 K
V = 1674.06 (11) Å3Needle, brown
Z = 40.57 × 0.09 × 0.08 mm
Data collection top
Bruker SMART APEXII CCD area-detector
diffractometer
4876 independent reflections
Radiation source: fine-focus sealed tube2723 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.061
Detector resolution: 8.33 pixels mm-1θmax = 30.0°, θmin = 2.6°
ω scansh = 1614
Absorption correction: multi-scan
(SADABS; Bruker, 2005)
k = 1722
Tmin = 0.943, Tmax = 0.992l = 1212
21832 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.061Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.166H atoms treated by a mixture of independent and constrained refinement
S = 1.05 w = 1/[σ2(Fo2) + (0.0731P)2]
where P = (Fo2 + 2Fc2)/3
4876 reflections(Δ/σ)max < 0.001
238 parametersΔρmax = 0.32 e Å3
0 restraintsΔρmin = 0.36 e Å3
Crystal data top
C14H19N5O4·H2OV = 1674.06 (11) Å3
Mr = 339.36Z = 4
Monoclinic, P21/cMo Kα radiation
a = 11.9683 (5) ŵ = 0.10 mm1
b = 15.7252 (6) ÅT = 100 K
c = 8.9289 (3) Å0.57 × 0.09 × 0.08 mm
β = 94.998 (2)°
Data collection top
Bruker SMART APEXII CCD area-detector
diffractometer
4876 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2005)
2723 reflections with I > 2σ(I)
Tmin = 0.943, Tmax = 0.992Rint = 0.061
21832 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0610 restraints
wR(F2) = 0.166H atoms treated by a mixture of independent and constrained refinement
S = 1.05Δρmax = 0.32 e Å3
4876 reflectionsΔρmin = 0.36 e Å3
238 parameters
Special details top

Experimental. The data was collected with the Oxford Cyrosystem Cobra low-temperature attachment.

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
xyzUiso*/Ueq
O1W0.33669 (13)0.55171 (10)0.83417 (19)0.0319 (4)
H2W0.3765 (19)0.5502 (14)0.916 (3)0.041 (7)*
H1W0.375 (2)0.5259 (17)0.776 (3)0.064 (9)*
N10.74698 (13)0.21118 (11)0.76942 (17)0.0226 (4)
H1N10.7338 (16)0.1598 (14)0.731 (2)0.030 (6)*
N20.65491 (14)0.33999 (10)0.80582 (17)0.0231 (4)
H1N20.6955 (18)0.3425 (13)0.887 (2)0.036 (6)*
N30.61656 (13)0.25861 (10)0.58549 (16)0.0224 (4)
N40.48333 (13)0.30708 (10)0.40139 (16)0.0235 (4)
N50.42175 (13)0.43870 (10)0.59176 (17)0.0280 (4)
O10.85318 (11)0.29207 (9)0.93866 (15)0.0299 (3)
O20.55239 (12)0.45420 (9)0.86810 (15)0.0358 (4)
O30.24515 (11)0.40072 (9)0.20062 (14)0.0320 (4)
O40.32505 (11)0.26822 (9)0.15833 (14)0.0301 (3)
C10.56955 (16)0.39795 (12)0.7781 (2)0.0255 (4)
C20.50631 (16)0.38486 (12)0.6321 (2)0.0236 (4)
C30.36985 (17)0.42572 (13)0.4568 (2)0.0289 (5)
H3A0.31000.46070.42410.035*
C40.40165 (16)0.36134 (13)0.3615 (2)0.0251 (4)
C50.53529 (15)0.31760 (12)0.54104 (19)0.0219 (4)
C60.66998 (15)0.27179 (11)0.7166 (2)0.0213 (4)
C70.83548 (15)0.22343 (12)0.8770 (2)0.0235 (4)
C80.90800 (16)0.14517 (12)0.9143 (2)0.0249 (4)
C91.00897 (17)0.17112 (14)1.0194 (2)0.0373 (5)
H9A1.05160.21320.97120.056*
H9B1.05510.12221.04330.056*
H9C0.98390.19441.11010.056*
C100.94675 (17)0.10571 (13)0.7706 (2)0.0327 (5)
H10A0.98290.14840.71490.049*
H10B0.88300.08360.71020.049*
H10C0.99860.06040.79670.049*
C110.83748 (17)0.08041 (13)0.9936 (2)0.0329 (5)
H11A0.81560.10451.08540.049*
H11B0.88100.03001.01580.049*
H11C0.77170.06620.92910.049*
C120.34396 (16)0.35271 (13)0.2031 (2)0.0273 (5)
H12A0.39240.37900.13320.033*
C130.19087 (18)0.41344 (14)0.0531 (2)0.0364 (5)
H13A0.13290.45540.05720.055*
H13B0.15850.36080.01610.055*
H13C0.24480.43270.01280.055*
C140.25935 (18)0.22090 (15)0.2566 (2)0.0375 (5)
H14A0.24770.16430.21820.056*
H14B0.18820.24840.26200.056*
H14C0.29830.21840.35510.056*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O1W0.0349 (9)0.0347 (9)0.0253 (8)0.0079 (7)0.0017 (7)0.0030 (7)
N10.0278 (9)0.0197 (9)0.0194 (8)0.0041 (7)0.0026 (7)0.0009 (7)
N20.0275 (9)0.0260 (9)0.0152 (8)0.0036 (7)0.0014 (7)0.0015 (7)
N30.0236 (8)0.0265 (9)0.0169 (8)0.0025 (7)0.0012 (6)0.0006 (6)
N40.0243 (9)0.0282 (9)0.0179 (8)0.0028 (7)0.0009 (7)0.0015 (6)
N50.0304 (9)0.0308 (9)0.0223 (8)0.0070 (7)0.0005 (7)0.0010 (7)
O10.0286 (8)0.0287 (8)0.0311 (8)0.0001 (6)0.0044 (6)0.0038 (6)
O20.0457 (9)0.0352 (8)0.0248 (7)0.0134 (7)0.0058 (7)0.0096 (6)
O30.0315 (8)0.0410 (9)0.0227 (7)0.0111 (6)0.0014 (6)0.0005 (6)
O40.0330 (8)0.0352 (9)0.0218 (7)0.0027 (6)0.0016 (6)0.0023 (6)
C10.0289 (11)0.0260 (11)0.0214 (9)0.0022 (8)0.0014 (8)0.0014 (8)
C20.0267 (10)0.0230 (10)0.0209 (9)0.0025 (8)0.0013 (8)0.0019 (8)
C30.0328 (11)0.0317 (12)0.0213 (10)0.0080 (9)0.0024 (8)0.0002 (8)
C40.0248 (10)0.0302 (11)0.0203 (9)0.0000 (8)0.0027 (8)0.0009 (8)
C50.0232 (10)0.0244 (10)0.0187 (9)0.0006 (8)0.0041 (7)0.0008 (8)
C60.0221 (10)0.0210 (10)0.0212 (9)0.0009 (8)0.0045 (8)0.0025 (7)
C70.0240 (10)0.0278 (11)0.0192 (9)0.0003 (8)0.0039 (8)0.0020 (8)
C80.0247 (10)0.0278 (11)0.0218 (9)0.0024 (8)0.0010 (8)0.0024 (8)
C90.0322 (12)0.0365 (13)0.0409 (13)0.0046 (10)0.0098 (10)0.0030 (10)
C100.0330 (12)0.0367 (12)0.0281 (11)0.0103 (9)0.0021 (9)0.0002 (9)
C110.0339 (12)0.0317 (12)0.0327 (11)0.0034 (10)0.0011 (9)0.0069 (9)
C120.0282 (11)0.0300 (11)0.0236 (10)0.0031 (9)0.0009 (8)0.0006 (8)
C130.0358 (12)0.0491 (14)0.0229 (10)0.0087 (11)0.0044 (9)0.0077 (10)
C140.0374 (13)0.0434 (14)0.0310 (12)0.0070 (10)0.0004 (10)0.0015 (10)
Geometric parameters (Å, º) top
O1W—H2W0.84 (2)C3—H3A0.9300
O1W—H1W0.83 (3)C4—C121.525 (3)
N1—C71.380 (2)C7—C81.526 (3)
N1—C61.380 (2)C8—C91.520 (3)
N1—H1N10.89 (2)C8—C101.533 (3)
N2—C61.358 (2)C8—C111.534 (3)
N2—C11.375 (2)C9—H9A0.9600
N2—H1N20.84 (2)C9—H9B0.9600
N3—C61.300 (2)C9—H9C0.9600
N3—C51.377 (2)C10—H10A0.9600
N4—C41.323 (2)C10—H10B0.9600
N4—C51.354 (2)C10—H10C0.9600
N5—C31.323 (2)C11—H11A0.9600
N5—C21.344 (2)C11—H11B0.9600
O1—C71.222 (2)C11—H11C0.9600
O2—C11.224 (2)C12—H12A0.9800
O3—C121.402 (2)C13—H13A0.9600
O3—C131.431 (2)C13—H13B0.9600
O4—C121.400 (2)C13—H13C0.9600
O4—C141.436 (2)C14—H14A0.9600
C1—C21.464 (3)C14—H14B0.9600
C2—C51.396 (3)C14—H14C0.9600
C3—C41.396 (3)
H2W—O1W—H1W104 (2)C10—C8—C11109.64 (17)
C7—N1—C6126.22 (17)C8—C9—H9A109.5
C7—N1—H1N1119.8 (13)C8—C9—H9B109.5
C6—N1—H1N1113.9 (13)H9A—C9—H9B109.5
C6—N2—C1123.54 (16)C8—C9—H9C109.5
C6—N2—H1N2116.6 (15)H9A—C9—H9C109.5
C1—N2—H1N2119.4 (15)H9B—C9—H9C109.5
C6—N3—C5115.57 (16)C8—C10—H10A109.5
C4—N4—C5116.01 (16)C8—C10—H10B109.5
C3—N5—C2115.46 (16)H10A—C10—H10B109.5
C12—O3—C13113.87 (15)C8—C10—H10C109.5
C12—O4—C14113.63 (15)H10A—C10—H10C109.5
O2—C1—N2121.69 (17)H10B—C10—H10C109.5
O2—C1—C2125.64 (17)C8—C11—H11A109.5
N2—C1—C2112.66 (16)C8—C11—H11B109.5
N5—C2—C5122.71 (17)H11A—C11—H11B109.5
N5—C2—C1117.96 (16)C8—C11—H11C109.5
C5—C2—C1119.33 (17)H11A—C11—H11C109.5
N5—C3—C4122.39 (18)H11B—C11—H11C109.5
N5—C3—H3A118.8O4—C12—O3113.05 (15)
C4—C3—H3A118.8O4—C12—C4113.46 (16)
N4—C4—C3122.53 (17)O3—C12—C4106.26 (15)
N4—C4—C12117.17 (16)O4—C12—H12A107.9
C3—C4—C12120.28 (17)O3—C12—H12A107.9
N4—C5—N3116.06 (16)C4—C12—H12A107.9
N4—C5—C2120.76 (17)O3—C13—H13A109.5
N3—C5—C2123.19 (16)O3—C13—H13B109.5
N3—C6—N2125.05 (17)H13A—C13—H13B109.5
N3—C6—N1117.33 (16)O3—C13—H13C109.5
N2—C6—N1117.62 (16)H13A—C13—H13C109.5
O1—C7—N1121.97 (17)H13B—C13—H13C109.5
O1—C7—C8122.73 (17)O4—C14—H14A109.5
N1—C7—C8115.29 (16)O4—C14—H14B109.5
C9—C8—C7108.96 (16)H14A—C14—H14B109.5
C9—C8—C10110.07 (17)O4—C14—H14C109.5
C7—C8—C10110.55 (15)H14A—C14—H14C109.5
C9—C8—C11109.47 (16)H14B—C14—H14C109.5
C7—C8—C11108.11 (15)
C6—N2—C1—O2173.22 (18)C5—N3—C6—N1175.91 (15)
C6—N2—C1—C27.8 (3)C1—N2—C6—N39.6 (3)
C3—N5—C2—C52.4 (3)C1—N2—C6—N1169.62 (16)
C3—N5—C2—C1177.85 (17)C7—N1—C6—N3158.04 (17)
O2—C1—C2—N50.1 (3)C7—N1—C6—N222.7 (3)
N2—C1—C2—N5178.98 (16)C6—N1—C7—O10.9 (3)
O2—C1—C2—C5179.84 (19)C6—N1—C7—C8179.91 (16)
N2—C1—C2—C51.2 (3)O1—C7—C8—C97.5 (3)
C2—N5—C3—C40.9 (3)N1—C7—C8—C9173.27 (16)
C5—N4—C4—C30.2 (3)O1—C7—C8—C10128.64 (19)
C5—N4—C4—C12178.21 (16)N1—C7—C8—C1052.2 (2)
N5—C3—C4—N42.3 (3)O1—C7—C8—C11111.3 (2)
N5—C3—C4—C12176.04 (18)N1—C7—C8—C1167.8 (2)
C4—N4—C5—N3176.92 (16)C14—O4—C12—O363.6 (2)
C4—N4—C5—C23.0 (3)C14—O4—C12—C457.4 (2)
C6—N3—C5—N4176.56 (16)C13—O3—C12—O466.3 (2)
C6—N3—C5—C23.5 (3)C13—O3—C12—C4168.57 (16)
N5—C2—C5—N44.6 (3)N4—C4—C12—O440.6 (2)
C1—C2—C5—N4175.67 (17)C3—C4—C12—O4140.96 (18)
N5—C2—C5—N3175.38 (17)N4—C4—C12—O3165.42 (16)
C1—C2—C5—N34.4 (3)C3—C4—C12—O316.1 (2)
C5—N3—C6—N23.3 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1W—H1W···O20.83 (3)2.48 (2)2.995 (2)121 (2)
O1W—H1W···N50.83 (3)2.25 (3)3.044 (2)161 (2)
O1W—H2W···O2i0.84 (3)2.04 (3)2.868 (2)170 (2)
N1—H1N1···O1Wii0.89 (2)1.96 (2)2.826 (2)164.0 (18)
N2—H1N2···O10.838 (19)2.06 (2)2.667 (2)128.8 (18)
N2—H1N2···N3iii0.838 (19)2.62 (2)3.008 (2)109.9 (17)
C3—H3A···O30.932.282.649 (2)103
C11—H11C···O1Wii0.962.593.471 (2)152
C14—H14C···N40.962.623.176 (3)117
C11—H11A···Cg1iv0.963.053.766 (2)132
C14—H14A···Cg2v0.963.333.718 (2)106
Symmetry codes: (i) x+1, y+1, z+2; (ii) x+1, y1/2, z+3/2; (iii) x, y+1/2, z+1/2; (iv) x, y1/2, z1/2; (v) x, y1/2, z3/2.

Experimental details

Crystal data
Chemical formulaC14H19N5O4·H2O
Mr339.36
Crystal system, space groupMonoclinic, P21/c
Temperature (K)100
a, b, c (Å)11.9683 (5), 15.7252 (6), 8.9289 (3)
β (°) 94.998 (2)
V3)1674.06 (11)
Z4
Radiation typeMo Kα
µ (mm1)0.10
Crystal size (mm)0.57 × 0.09 × 0.08
Data collection
DiffractometerBruker SMART APEXII CCD area-detector
Absorption correctionMulti-scan
(SADABS; Bruker, 2005)
Tmin, Tmax0.943, 0.992
No. of measured, independent and
observed [I > 2σ(I)] reflections
21832, 4876, 2723
Rint0.061
(sin θ/λ)max1)0.703
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.061, 0.166, 1.05
No. of reflections4876
No. of parameters238
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.32, 0.36

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXTL (Sheldrick, 1998) and PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1W—H1W···O20.83 (3)2.48 (2)2.995 (2)121 (2)
O1W—H1W···N50.83 (3)2.25 (3)3.044 (2)161 (2)
O1W—H2W···O2i0.84 (3)2.04 (3)2.868 (2)170 (2)
N1—H1N1···O1Wii0.89 (2)1.96 (2)2.826 (2)164.0 (18)
N2—H1N2···O10.838 (19)2.06 (2)2.667 (2)128.8 (18)
N2—H1N2···N3iii0.838 (19)2.62 (2)3.008 (2)109.9 (17)
C3—H3A···O30.932.28122.649 (2)103
C11—H11C···O1Wii0.962.59413.471 (2)152
C14—H14C···N40.962.61923.176 (3)117
C11—H11A···Cg1iv0.963.05083.766 (2)132
C14—H14A···Cg2v0.963.33243.718 (2)106
Symmetry codes: (i) x+1, y+1, z+2; (ii) x+1, y1/2, z+3/2; (iii) x, y+1/2, z+1/2; (iv) x, y1/2, z1/2; (v) x, y1/2, z3/2.
 

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