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Acta Cryst. (2007). E63, o4408-o4409
https://doi.org/10.1107/S1600536807051276
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2,6-Diamino-5-(2,4-diamino-6-oxo-1,6-dihydro­pyrimidin-5-ylmeth­yl)-4-oxo­pyrimidin-1-ium 3,5-dinitro­benzoate

A. Subashini, P. T. Muthiah, G. Bocelli and A. Cantoni
In the title compound, C9H13N8O2+·C7H3N2O6−, the amino­pyrimidine mol­ecule is protonated at one of the pyrimidine N atoms. The carboxyl­ate group of the 3,5-dinitro­benzoate anion inter­acts with the protonated N atom and the 2-amino group in a nearly linear fashion through a pair of N—H...O hydrogen bonds, generating the typical R22(8) motif. Two inversion-related pyrimidine units are connected through a pair of N—H...N hydrogen bonds, forming a cyclic hydrogen-bonded R22(8) motif. In addition to the base pairing, one of the carboxyl­ate O atoms bridges the 4′-amino and 6′-amino groups on both side of the pairing, forming a DADA array. The mol­ecular conformation of the cation is stabilized by two intra­molecular N—H...O hydrogen bonds.
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Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807051276/bt2550sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807051276/bt2550Isup2.hkl
Contains datablock I

CCDC reference: 639719

checkCIF report

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.044
  • wR factor = 0.129
  • Data-to-parameter ratio = 13.7

checkCIF/PLATON results

No syntax errors found




Alert level A
PLAT029_ALERT_3_A _diffrn_measured_fraction_theta_full Low .......       0.88
Author Response: The crystals may be of poor quality. 



Alert level B
REFLT03_ALERT_3_B  Reflection count < 90% complete (theta max?)
           From the CIF: _diffrn_reflns_theta_max           27.98
           From the CIF: _diffrn_reflns_theta_full          27.98
           From the CIF: _reflns_number_total               4216
           TEST2: Reflns within _diffrn_reflns_theta_max
           Count of symmetry unique reflns         4779
           Completeness (_total/calc)             88.22%


Alert level C
PLAT230_ALERT_2_C Hirshfeld Test Diff for    O1'    -   C2'     ..       5.08 su
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         N7
PLAT420_ALERT_2_C D-H Without Acceptor       N6     -   H6B    ...          ?
PLAT432_ALERT_2_C Short Inter X...Y Contact  O7     ..  C14     ..       2.99 Ang.
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          4
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          2
              C7 H3 N2 O6


Alert level G
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K


   1 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
   6 ALERT level C = Check and explain
   2 ALERT level G = General alerts; check

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   4 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check
Comment top

Pyrimidine and aminopyrimidine derivatives are biologically important compounds as they occur in nature as components of nucleic acids. Some aminopyrimidine derivatives are used as antifolate drugs (Hunt et al., 1980; Baker & Santi, 1965). Hydrogen-bonding patterns involving aminopyrimidine and carboxylates have been observed in drug-receptor interactions, protein-nucleic acid interactions and supramolecular architectures (Desiraju, 1989). Studies of such interactions are also of current interest because of their applications in drug design and the crystal engineering of pharmaceuticals (Stanley et al., 2005). Two monoclinic polymorphic forms of 3,5-dinitrobenzoic acid (Prince et al., 1991) have already been reported in literature. From our laboratory the crystal structures of trimethoprim (TMP) 3,5-dinitrobenzoate (Francis, 2003), TMP-3,5-dinitrosalicylate (Subashini, Samuel et al., 2007) and pyrimethamine (PMN) 3,5-dinitrobenzoate (Subashini, Muthiah et al., 2007) have been reported.

The asymmetric unit of the title compound contains a protonated 2,6-diamino-4-oxopyrimidinium -5-methylene-2'-oxo-4',6'-diaminopyrimidine (DAMPY) cation and a 3,5-dinitro benzoate anion (Fig.1). The DAMPY cation consists of one pyrimidinium cation and a neutral pyrimidine molecule bridged by a methylene group. The protonation at N1 of the pyrimidine moiety is evident from the increase in the internal angle at N1 (C2—N1—C6) from 116.4 (2)° in neutral 2,6-diamino-4(3H)-pyrimidinone monohydrate (Skoweranda et al., 1990) to 121.02 (14)° in the present study. The carboxylate group (atoms O2 and O3) of the 3,5-dinitrobenzoate anion interact with the protonated atom N1 and the 2-amino group of the pyrimidine moiety through a pair of N—H···O hydrogen bonds, leading to the common ring motif with graph-set notation R22(8) (Lynch & Jones, 2004). This motif is reminiscent of the cyclic hydrogen-bonded motif occurring in the crystal structures of many aminopyrimidine carboxylates (Allen et al., 1998; Raj et al., 2003). Adjacent pyrimidinium cations are linked together by way of N—H···O bonds from the N3 and N2 amino donors to the O1' keto acceptor, resulting in chains containing R12(6) rings (Etter, 1990; Bernstein et al., 1995). Two inversion related pyrimidine groups are paired centrosymmetrically through N4'-H4A'···N5'hydrogen bonds generating the R22(8) ring motif. In addition to the base-pairing, one of the carboxylate oxygen atoms (O3) bridges the 4'-amino and the 6'-amino groups on both sides of the pairing. This combination of base-pairing patterns and the further bridging of the bases leads to the formation of array of four hydrogen bonds. This is called a complementary DADA array of quadruple hydrogen bonding patterns (D = hydrogen bond donor and A = hydrogen bond acceptor) (Fig 2). The N3' atom and the 4'-amino group are hydrogen bonded to the oxygen atoms (O6 & O7) of the nitro group through a pair of N—H···O hydrogen bonds, generating the common R22(8) ring motif. The R22(8) motif is frequently observed in aminopyrimidine-carboxylate (Lynch & Jones, 2004) salts. Here, the nitro group mimics the role of carboxylate group. There is intramolecular hydrogen bonding between the N6/N6' amino groups and O1'/O1 keto groups. Further, N3' atom acts as a bifurcated donor to the nitro oxygen (O6 & O7) atoms. The combination of all types of intermolecular hydrogen bonds forms a three-dimensional network (Fig. 3).

Related literature top

For related literature, see: Allen et al. (1998); Baker & Santi (1965); Bernstein et al. (1995); Desiraju (1989); Etter (1990); Francis (2003); Hunt et al. (1980); Lynch & Jones (2004); Prince et al. (1991); Raj et al. (2003); Stanley et al. (2005); Subashini, Samuel et al. (2007); Subashini, Muthiah et al. (2007); Skoweranda et al. (1990).

Experimental top

A hot methanol solution of 2,6-diamino-pyrimidin-4(3H)one (62 mg, Aldrich) was added to a hot aqueous solution of 3,5- dinitrobenzoic acid (53 mg, Aldrich) in a 2:1 molar ratio. A few drops of formaldehyde were added to the above solution. The resultant solution was warmed over a water bath for four hours. After a few days plate-like red crystals were obtained from the mother liquor.

Refinement top

All hydrogen atoms were placed in idealized locations and refined as riding with C—H and N—H bond lengths of 0.97 Å and 0.86 Å, respectively, and U(H) = 1.2Ueq(C,N).

Structure description top

Pyrimidine and aminopyrimidine derivatives are biologically important compounds as they occur in nature as components of nucleic acids. Some aminopyrimidine derivatives are used as antifolate drugs (Hunt et al., 1980; Baker & Santi, 1965). Hydrogen-bonding patterns involving aminopyrimidine and carboxylates have been observed in drug-receptor interactions, protein-nucleic acid interactions and supramolecular architectures (Desiraju, 1989). Studies of such interactions are also of current interest because of their applications in drug design and the crystal engineering of pharmaceuticals (Stanley et al., 2005). Two monoclinic polymorphic forms of 3,5-dinitrobenzoic acid (Prince et al., 1991) have already been reported in literature. From our laboratory the crystal structures of trimethoprim (TMP) 3,5-dinitrobenzoate (Francis, 2003), TMP-3,5-dinitrosalicylate (Subashini, Samuel et al., 2007) and pyrimethamine (PMN) 3,5-dinitrobenzoate (Subashini, Muthiah et al., 2007) have been reported.

The asymmetric unit of the title compound contains a protonated 2,6-diamino-4-oxopyrimidinium -5-methylene-2'-oxo-4',6'-diaminopyrimidine (DAMPY) cation and a 3,5-dinitro benzoate anion (Fig.1). The DAMPY cation consists of one pyrimidinium cation and a neutral pyrimidine molecule bridged by a methylene group. The protonation at N1 of the pyrimidine moiety is evident from the increase in the internal angle at N1 (C2—N1—C6) from 116.4 (2)° in neutral 2,6-diamino-4(3H)-pyrimidinone monohydrate (Skoweranda et al., 1990) to 121.02 (14)° in the present study. The carboxylate group (atoms O2 and O3) of the 3,5-dinitrobenzoate anion interact with the protonated atom N1 and the 2-amino group of the pyrimidine moiety through a pair of N—H···O hydrogen bonds, leading to the common ring motif with graph-set notation R22(8) (Lynch & Jones, 2004). This motif is reminiscent of the cyclic hydrogen-bonded motif occurring in the crystal structures of many aminopyrimidine carboxylates (Allen et al., 1998; Raj et al., 2003). Adjacent pyrimidinium cations are linked together by way of N—H···O bonds from the N3 and N2 amino donors to the O1' keto acceptor, resulting in chains containing R12(6) rings (Etter, 1990; Bernstein et al., 1995). Two inversion related pyrimidine groups are paired centrosymmetrically through N4'-H4A'···N5'hydrogen bonds generating the R22(8) ring motif. In addition to the base-pairing, one of the carboxylate oxygen atoms (O3) bridges the 4'-amino and the 6'-amino groups on both sides of the pairing. This combination of base-pairing patterns and the further bridging of the bases leads to the formation of array of four hydrogen bonds. This is called a complementary DADA array of quadruple hydrogen bonding patterns (D = hydrogen bond donor and A = hydrogen bond acceptor) (Fig 2). The N3' atom and the 4'-amino group are hydrogen bonded to the oxygen atoms (O6 & O7) of the nitro group through a pair of N—H···O hydrogen bonds, generating the common R22(8) ring motif. The R22(8) motif is frequently observed in aminopyrimidine-carboxylate (Lynch & Jones, 2004) salts. Here, the nitro group mimics the role of carboxylate group. There is intramolecular hydrogen bonding between the N6/N6' amino groups and O1'/O1 keto groups. Further, N3' atom acts as a bifurcated donor to the nitro oxygen (O6 & O7) atoms. The combination of all types of intermolecular hydrogen bonds forms a three-dimensional network (Fig. 3).

For related literature, see: Allen et al. (1998); Baker & Santi (1965); Bernstein et al. (1995); Desiraju (1989); Etter (1990); Francis (2003); Hunt et al. (1980); Lynch & Jones (2004); Prince et al. (1991); Raj et al. (2003); Stanley et al. (2005); Subashini, Samuel et al. (2007); Subashini, Muthiah et al. (2007); Skoweranda et al. (1990).

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SMART (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: PLATON (Spek, 2003).

Figures top
[Figure 1] Fig. 1. An ORTEP diagram of the asymmetric unit of (I) showing 30% probability displacement ellipsoids.
[Figure 2] Fig. 2. View of DADA array in compound (I). Symmetry Codes: (i) -x + 1/2,y - 1/2,-z + 1/2; (iii) -x - 1/2,y - 1/2,-z - 1/2; (iv) -x + 1,-y,-z: (v) x + 1/2,-y + 1/2,z - 1/2.
[Figure 3] Fig. 3. Overall packing view of compound (I).
2,6-Diamino-5-(2,4-diamino-6-oxo-1,6-dihydropyrimidin-5-ylmethyl)-4- oxopyrimidin-1-ium 3,5-dinitrobenzoate top
Crystal data top
C9H13N8O2+·C7H3N2O6−F(000) = 984
Mr = 476.39Dx = 1.591 Mg m−3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 25 reflections
a = 7.365 (2) Åθ = 1.8–28.0°
b = 19.788 (3) ŵ = 0.13 mm−1
c = 13.658 (2) ÅT = 293 K
β = 92.70 (2)°Plate-like, dark-red
V = 1988.3 (7) Å30.16 × 0.13 × 0.11 mm
Z = 4
Data collection top
Bruker SMART CCD
diffractometer		3046 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.027
Graphite monochromatorθmax = 28.0°, θmin = 1.8°
ω scansh = −9→9
14081 measured reflectionsk = −24→25
4216 independent reflectionsl = −18→15
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)] = 0.044Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.129H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0811P)2]
where P = (Fo2 + 2Fc2)/3
4216 reflections(Δ/σ)max < 0.001
307 parametersΔρmax = 0.30 e Å−3
0 restraintsΔρmin = −0.20 e Å−3
Crystal data top
C9H13N8O2+·C7H3N2O6−V = 1988.3 (7) Å3
Mr = 476.39Z = 4
Monoclinic, P21/nMo Kα radiation
a = 7.365 (2) ŵ = 0.13 mm−1
b = 19.788 (3) ÅT = 293 K
c = 13.658 (2) Å0.16 × 0.13 × 0.11 mm
β = 92.70 (2)°
Data collection top
Bruker SMART CCD
diffractometer		3046 reflections with I > 2σ(I)
14081 measured reflectionsRint = 0.027
4216 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0440 restraints
wR(F2) = 0.129H-atom parameters constrained
S = 1.03Δρmax = 0.30 e Å−3
4216 reflectionsΔρmin = −0.20 e Å−3
307 parameters
Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All e.s.d.'s are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2> σ(F2) is used only for calculating -R-factor-obs 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
O10.14706 (18)0.18678 (6)0.35996 (9)0.0561 (4)
O1'−0.17937 (15)0.13724 (6)−0.02359 (9)0.0505 (4)
N1−0.02333 (17)0.33870 (7)0.18543 (10)0.0427 (4)
N20.1212 (2)0.41207 (8)0.29440 (11)0.0529 (5)
N30.13675 (19)0.29771 (7)0.32142 (10)0.0466 (5)
N3'0.07063 (18)0.07452 (7)−0.05341 (10)0.0453 (4)
N4'0.3125 (2)0.00855 (8)−0.09363 (11)0.0544 (5)
N5'0.29913 (18)0.04685 (7)0.06500 (10)0.0434 (4)
N6−0.1676 (2)0.26934 (8)0.07117 (11)0.0559 (5)
N6'0.2848 (2)0.08959 (8)0.21976 (11)0.0537 (5)
C1'0.0347 (2)0.11346 (8)0.10752 (11)0.0394 (5)
C20.0773 (2)0.34998 (8)0.26789 (12)0.0406 (5)
C2'−0.0325 (2)0.11055 (8)0.01073 (12)0.0412 (5)
C40.0916 (2)0.23008 (9)0.30063 (12)0.0435 (5)
C4'0.2293 (2)0.04365 (8)−0.02568 (12)0.0416 (5)
C5−0.0150 (2)0.21896 (8)0.21273 (12)0.0410 (5)
C6−0.0688 (2)0.27348 (8)0.15603 (12)0.0410 (5)
C6'0.2048 (2)0.08402 (8)0.13017 (12)0.0409 (5)
C7−0.0736 (2)0.14767 (8)0.18496 (12)0.0442 (5)
O2−0.16430 (17)0.43773 (6)0.07378 (9)0.0530 (4)
O3−0.07352 (19)0.51100 (7)0.18985 (10)0.0636 (5)
O4−0.1547 (3)0.75282 (9)0.12584 (16)0.1066 (9)
O5−0.3364 (3)0.78625 (8)0.00784 (15)0.0989 (8)
O6−0.5558 (2)0.62731 (9)−0.23607 (11)0.0798 (6)
O7−0.5115 (2)0.52095 (8)−0.21502 (10)0.0656 (5)
N7−0.2520 (3)0.74235 (9)0.05372 (15)0.0695 (7)
N8−0.4934 (2)0.57961 (9)−0.18840 (11)0.0530 (5)
C8−0.2224 (2)0.55403 (8)0.04574 (12)0.0414 (5)
C9−0.1993 (2)0.62059 (9)0.07690 (13)0.0478 (6)
C10−0.2749 (2)0.67215 (9)0.01992 (14)0.0498 (6)
C11−0.3740 (2)0.66040 (9)−0.06636 (13)0.0499 (6)
C12−0.3926 (2)0.59391 (9)−0.09554 (12)0.0440 (5)
C13−0.3183 (2)0.54039 (9)−0.04180 (12)0.0417 (5)
C14−0.1460 (2)0.49614 (9)0.10781 (13)0.0450 (5)
H1−0.060500.372400.150100.0510*
H6A'0.388100.070500.232800.0640*
H6B'0.233100.112200.264400.0640*
H2A0.082400.445700.259500.0630*
H2B0.188700.418900.346600.0630*
H30.207300.305800.372000.0560*
H3'0.032400.07160−0.113700.0540*
H4A'0.41250−0.01230−0.078500.0650*
H4B'0.266300.00670−0.152600.0650*
H6A−0.201800.230500.048800.0670*
H6B−0.196800.305500.039200.0670*
H7A−0.066400.120000.243600.0530*
H7B−0.200100.149000.161800.0530*
H9−0.133900.630200.135100.0570*
H11−0.425900.69550−0.103200.0600*
H13−0.332400.49620−0.064100.0500*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0745 (8)0.0519 (7)0.0404 (7)0.0040 (6)−0.0138 (6)0.0025 (6)
O1'0.0486 (6)0.0573 (7)0.0440 (7)0.0097 (5)−0.0154 (5)0.0005 (5)
N10.0461 (7)0.0411 (7)0.0398 (8)0.0077 (6)−0.0082 (6)−0.0018 (6)
N20.0595 (9)0.0471 (9)0.0504 (9)0.0016 (7)−0.0150 (7)−0.0067 (7)
N30.0503 (8)0.0503 (9)0.0378 (8)0.0013 (6)−0.0127 (6)−0.0040 (6)
N3'0.0485 (7)0.0545 (8)0.0319 (7)0.0044 (6)−0.0075 (6)−0.0021 (6)
N4'0.0516 (8)0.0698 (10)0.0414 (8)0.0093 (7)−0.0032 (7)−0.0080 (7)
N5'0.0447 (7)0.0439 (8)0.0407 (8)0.0034 (6)−0.0073 (6)−0.0019 (6)
N60.0668 (9)0.0488 (8)0.0498 (9)0.0073 (7)−0.0219 (7)−0.0056 (7)
N6'0.0576 (9)0.0603 (10)0.0417 (8)0.0160 (7)−0.0148 (7)−0.0063 (7)
C1'0.0431 (8)0.0373 (8)0.0369 (9)0.0010 (6)−0.0068 (7)0.0010 (6)
C20.0380 (7)0.0448 (9)0.0388 (9)0.0032 (6)−0.0015 (6)−0.0057 (7)
C2'0.0438 (8)0.0384 (8)0.0408 (9)−0.0014 (7)−0.0057 (7)0.0022 (7)
C40.0463 (9)0.0481 (10)0.0358 (9)0.0041 (7)−0.0018 (7)−0.0014 (7)
C4'0.0413 (8)0.0412 (9)0.0418 (9)−0.0029 (7)−0.0026 (7)0.0020 (7)
C50.0418 (8)0.0438 (9)0.0370 (9)0.0036 (7)−0.0019 (7)−0.0044 (7)
C60.0386 (8)0.0451 (9)0.0388 (9)0.0049 (7)−0.0033 (7)−0.0070 (7)
C6'0.0470 (8)0.0366 (8)0.0383 (9)−0.0011 (7)−0.0075 (7)0.0022 (7)
C70.0473 (9)0.0451 (9)0.0396 (9)−0.0006 (7)−0.0032 (7)0.0011 (7)
O20.0637 (7)0.0443 (7)0.0494 (7)0.0036 (5)−0.0145 (6)−0.0006 (5)
O30.0738 (9)0.0588 (8)0.0552 (8)−0.0089 (6)−0.0301 (7)0.0021 (6)
O40.1656 (19)0.0644 (11)0.0883 (14)−0.0240 (11)−0.0110 (14)−0.0248 (9)
O50.1369 (16)0.0435 (9)0.1173 (15)−0.0002 (10)0.0165 (13)0.0075 (9)
O60.1006 (12)0.0851 (11)0.0517 (9)0.0199 (9)−0.0167 (8)0.0157 (8)
O70.0696 (8)0.0749 (10)0.0509 (8)0.0031 (7)−0.0127 (7)−0.0091 (7)
N70.0960 (14)0.0448 (10)0.0698 (13)−0.0107 (9)0.0257 (11)−0.0044 (9)
N80.0529 (8)0.0671 (11)0.0386 (8)0.0062 (8)−0.0020 (7)0.0070 (8)
C80.0385 (8)0.0441 (9)0.0413 (9)−0.0038 (6)−0.0006 (7)0.0001 (7)
C90.0515 (9)0.0498 (10)0.0418 (10)−0.0084 (8)0.0003 (7)−0.0041 (8)
C100.0583 (10)0.0415 (10)0.0508 (11)−0.0045 (8)0.0163 (8)−0.0005 (8)
C110.0548 (10)0.0484 (10)0.0473 (10)0.0065 (8)0.0117 (8)0.0102 (8)
C120.0427 (8)0.0528 (10)0.0365 (9)0.0018 (7)0.0026 (7)0.0042 (7)
C130.0413 (8)0.0429 (9)0.0407 (9)−0.0018 (7)0.0004 (7)0.0004 (7)
C140.0414 (8)0.0485 (10)0.0441 (10)−0.0034 (7)−0.0078 (7)0.0032 (7)
Geometric parameters (Å, º) top
O1—C41.235 (2)N4'—H4B'0.8602
O1'—C2'1.2732 (19)N6—H6A0.8604
O2—C141.251 (2)N6—H6B0.8603
O3—C141.253 (2)N6'—H6B'0.8595
O4—N71.208 (3)N6'—H6A'0.8605
O5—N71.224 (3)N7—C101.471 (3)
O6—N81.224 (2)N8—C121.467 (2)
O7—N81.222 (2)C1'—C6'1.403 (2)
N1—C21.337 (2)C1'—C71.514 (2)
N1—C61.388 (2)C1'—C2'1.391 (2)
N2—C21.317 (2)C4—C51.420 (2)
N3—C41.405 (2)C5—C71.518 (2)
N3—C21.329 (2)C5—C61.375 (2)
N3'—C2'1.384 (2)C7—H7A0.9696
N3'—C4'1.357 (2)C7—H7B0.9701
N4'—C4'1.331 (2)C8—C91.392 (2)
N5'—C4'1.320 (2)C8—C131.386 (2)
N5'—C6'1.369 (2)C8—C141.517 (2)
N6—C61.342 (2)C9—C101.384 (3)
N6'—C6'1.337 (2)C10—C111.376 (3)
N1—H10.8603C11—C121.380 (3)
N2—H2B0.8604C12—C131.386 (2)
N2—H2A0.8596C9—H90.9295
N3—H30.8597C11—H110.9293
N3'—H3'0.8596C13—H130.9302
N4'—H4A'0.8608
O1···N6'2.929 (2)C4···N7ii3.277 (3)
O1···N6i3.251 (2)C4···N6'3.335 (2)
O1···C10ii3.273 (2)C4'···N3'xi3.426 (2)
O1'···N2iii2.991 (2)C4'···C2'xi3.388 (2)
O1'···N3iii2.775 (2)C5···N6'3.379 (2)
O1'···C2iii3.302 (2)C6'···O7i3.412 (2)
O1'···N62.916 (2)C6'···O5iv3.355 (3)
O2···N12.663 (2)C8···O2iv3.353 (2)
O2···C8iv3.353 (2)C10···O1xvi3.273 (2)
O2···N8v3.049 (2)C11···N1iv3.414 (2)
O2···C12v3.350 (2)C12···N2iv3.449 (2)
O3···N22.781 (2)C12···C2iv3.561 (2)
O3···O7v3.156 (2)C12···O2v3.350 (2)
O3···N6'vi2.867 (2)C13···C13v3.363 (2)
O3···N4'vii3.136 (2)C14···N13.399 (2)
O4···O6viii3.096 (3)C14···N8v3.284 (2)
O5···C1'iv3.419 (3)C14···O7v2.995 (2)
O5···C6'iv3.355 (3)C1'···H6A2.9849
O5···C2'iv3.418 (3)C2'···H2Biii3.0245
O6···O4ix3.096 (3)C2'···H6A2.7423
O6···N3'x3.056 (2)C4···H6B'2.6116
O7···C14v2.995 (2)C4'···H4A'xiv3.0026
O7···O3v3.156 (2)C5···H6B'2.8598
O7···C6'iii3.412 (2)C7···H6B'2.5576
O7···N6'iii3.244 (2)C7···H6A2.6212
O1···H6Bi2.6596C9···H7Axvi3.0638
O1···H6B'2.0883C13···H13v3.0960
O1···H7A2.5511C14···H12.5868
O1'···H7B2.5544C14···H2A2.7910
O1'···H3iii1.9719H1···C142.5868
O1'···H6A2.1038H1···H2A2.3013
O1'···H2Biii2.2714H1···O21.8075
O2···H11.8075H1···O32.7984
O2···H6B2.6676H1···H6B2.2161
O2···H132.4896H6A'···O3xv2.0570
O3···H2A1.9469H6A'···H2Axv2.4809
O3···H92.5078H6B'···C72.5576
O3···H4B'vii2.5266H6B'···H7A2.2161
O3···H6A'vi2.0570H6B'···C52.8598
O3···H12.7984H6B'···O12.0883
O4···H92.4341H6B'···C42.6116
O5···H112.4218H2A···O31.9469
O6···H3'x2.3427H2A···H6A'vi2.4809
O6···H112.4219H2A···C142.7910
O7···H4B'x2.5594H2A···H12.3013
O7···H3'x2.5430H2B···C2'i3.0245
O7···H132.4439H2B···H32.2679
O7···H7Aiii2.8706H2B···N5'vi2.8046
N1···C143.399 (2)H2B···O1'i2.2714
N1···C11iv3.414 (2)H2B···H3'i2.5706
N1···O22.663 (2)H3···H2B2.2679
N2···N8iv3.164 (2)H3···O1'i1.9719
N2···C12iv3.449 (2)H3···H6Ai2.5774
N2···O32.781 (2)H3'···O7xii2.5430
N2···N4'vii3.210 (2)H3'···N8xii2.7093
N2···O1'i2.991 (2)H3'···O6xii2.3427
N3···O1'i2.775 (2)H3'···H4B'2.2328
N3'···C4'xi3.426 (2)H3'···H2Biii2.5706
N3'···O6xii3.056 (2)H4A'···N5'xiv2.2305
N4'···O3xiii3.136 (2)H4A'···C4'xiv3.0026
N4'···C2'xi3.363 (2)H4A'···H4A'xiv2.4972
N4'···N5'xiv3.071 (2)H4B'···O7xii2.5594
N4'···N2xiii3.210 (2)H4B'···O3xiii2.5266
N5'···N4'xiv3.071 (2)H4B'···H3'2.2328
N6···O1iii3.251 (2)H6A···H3iii2.5774
N6···C2'3.409 (2)H6A···C1'2.9849
N6···O1'2.916 (2)H6A···C2'2.7423
N6'···O12.929 (2)H6A···O1'2.1038
N6'···O7i3.244 (2)H6A···H7B2.2318
N6'···O3xv2.867 (2)H6A···C72.6212
N6'···C43.335 (2)H6B···O22.6676
N6'···C53.379 (2)H6B···O1iii2.6596
N7···C4xvi3.277 (3)H6B···H12.2161
N8···N2iv3.164 (2)H7A···O12.5511
N8···C14v3.284 (2)H7A···N6'2.6903
N8···O2v3.049 (2)H7A···H6B'2.2161
N5'···H4A'xiv2.2305H7A···C9ii3.0638
N5'···H2Bxv2.8046H7A···O7i2.8706
N6···H7B2.6996H7B···O1'2.5544
N6'···H7A2.6903H7B···N62.6996
N8···H3'x2.7093H7B···H6A2.2318
C1'···O5iv3.419 (3)H9···O32.5078
C2···O1'i3.302 (2)H9···O42.4341
C2···C12iv3.561 (2)H11···O52.4218
C2'···C4'xi3.388 (2)H11···O62.4219
C2'···N63.409 (2)H13···O22.4896
C2'···O5iv3.418 (3)H13···O72.4439
C2'···N4'xi3.363 (2)H13···C13v3.0960
C2—N1—C6121.02 (14)N4'—C4'—N5'120.48 (14)
C2—N3—C4124.17 (14)N3'—C4'—N5'122.19 (15)
C2'—N3'—C4'123.12 (14)N3'—C4'—N4'117.32 (15)
C4'—N5'—C6'116.65 (14)C4—C5—C7119.63 (14)
C2—N1—H1119.47C4—C5—C6119.18 (15)
C6—N1—H1119.50C6—C5—C7121.15 (14)
C2—N2—H2A119.93N6—C6—C5124.66 (15)
H2A—N2—H2B120.13N1—C6—C5120.48 (15)
C2—N2—H2B119.95N1—C6—N6114.86 (14)
C2—N3—H3117.92N6'—C6'—C1'121.19 (15)
C4—N3—H3117.92N5'—C6'—C1'123.71 (15)
C4'—N3'—H3'118.43N5'—C6'—N6'115.08 (14)
C2'—N3'—H3'118.44C1'—C7—C5115.92 (13)
H4A'—N4'—H4B'120.04H7A—C7—H7B107.40
C4'—N4'—H4A'119.96C1'—C7—H7A108.33
C4'—N4'—H4B'120.01C1'—C7—H7B108.29
H6A—N6—H6B120.05C5—C7—H7A108.33
C6—N6—H6A119.94C5—C7—H7B108.28
C6—N6—H6B120.01C9—C8—C13119.86 (15)
C6'—N6'—H6A'120.02C9—C8—C14120.44 (15)
H6A'—N6'—H6B'119.91C13—C8—C14119.69 (15)
C6'—N6'—H6B'120.07C8—C9—C10119.04 (16)
O4—N7—O5124.3 (2)N7—C10—C9118.85 (17)
O4—N7—C10118.20 (18)N7—C10—C11118.46 (17)
O5—N7—C10117.50 (19)C9—C10—C11122.68 (17)
O6—N8—C12118.25 (17)C10—C11—C12116.73 (16)
O7—N8—C12118.97 (16)N8—C12—C11118.24 (15)
O6—N8—O7122.78 (16)N8—C12—C13118.79 (16)
C6'—C1'—C7121.73 (14)C11—C12—C13122.97 (15)
C2'—C1'—C6'117.81 (14)C8—C13—C12118.70 (16)
C2'—C1'—C7120.46 (14)O2—C14—O3125.66 (17)
N1—C2—N2120.42 (15)O2—C14—C8117.35 (15)
N1—C2—N3119.24 (15)O3—C14—C8116.97 (16)
N2—C2—N3120.31 (15)C8—C9—H9120.39
N3'—C2'—C1'116.21 (14)C10—C9—H9120.57
O1'—C2'—C1'126.22 (15)C10—C11—H11121.69
O1'—C2'—N3'117.57 (14)C12—C11—H11121.58
N3—C4—C5115.76 (15)C8—C13—H13120.66
O1—C4—N3117.41 (15)C12—C13—H13120.64
O1—C4—C5126.83 (16)
C6—N1—C2—N2179.24 (15)C2'—C1'—C6'—N5'−6.9 (2)
C6—N1—C2—N31.1 (2)C2'—C1'—C6'—N6'174.52 (15)
C2—N1—C6—N6−178.93 (14)C7—C1'—C6'—N6'−5.3 (2)
C2—N1—C6—C51.7 (2)C2'—C1'—C7—C5−100.30 (17)
C4—N3—C2—N1−4.2 (2)O1—C4—C5—C70.8 (2)
C4—N3—C2—N2177.67 (15)N3—C4—C5—C6−1.2 (2)
C2—N3—C4—O1−175.53 (15)O1—C4—C5—C6178.47 (16)
C2—N3—C4—C54.2 (2)N3—C4—C5—C7−178.87 (13)
C4'—N3'—C2'—O1'−179.83 (14)C6—C5—C7—C1'80.93 (18)
C4'—N3'—C2'—C1'−0.4 (2)C7—C5—C6—N6−3.2 (2)
C2'—N3'—C4'—N4'177.70 (15)C4—C5—C7—C1'−101.45 (17)
C2'—N3'—C4'—N5'−1.3 (2)C4—C5—C6—N1−1.5 (2)
C6'—N5'—C4'—N3'−1.0 (2)C4—C5—C6—N6179.18 (15)
C6'—N5'—C4'—N4'−180.00 (15)C7—C5—C6—N1176.09 (14)
C4'—N5'—C6'—N6'−176.13 (15)C13—C8—C9—C100.7 (2)
C4'—N5'—C6'—C1'5.2 (2)C14—C8—C9—C10−178.25 (14)
O4—N7—C10—C96.2 (3)C9—C8—C13—C12−1.3 (2)
O4—N7—C10—C11−175.0 (2)C14—C8—C13—C12177.66 (14)
O5—N7—C10—C9−172.20 (19)C9—C8—C14—O2−176.92 (15)
O5—N7—C10—C116.5 (3)C9—C8—C14—O34.6 (2)
O6—N8—C12—C110.3 (2)C13—C8—C14—O24.1 (2)
O7—N8—C12—C11−179.76 (15)C13—C8—C14—O3−174.33 (15)
O6—N8—C12—C13−178.79 (15)C8—C9—C10—N7179.28 (16)
O7—N8—C12—C131.1 (2)C8—C9—C10—C110.6 (2)
C7—C1'—C2'—N3'−175.99 (14)N7—C10—C11—C12−179.93 (17)
C6'—C1'—C2'—O1'−176.43 (15)C9—C10—C11—C12−1.2 (2)
C7—C1'—C2'—O1'3.4 (2)C10—C11—C12—N8−178.47 (14)
C6'—C1'—C2'—N3'4.2 (2)C10—C11—C12—C130.6 (2)
C6'—C1'—C7—C579.49 (19)N8—C12—C13—C8179.72 (14)
C7—C1'—C6'—N5'173.27 (15)C11—C12—C13—C80.7 (2)
Symmetry codes: (i) x+1/2, −y+1/2, z+1/2; (ii) −x−1/2, y−1/2, −z+1/2; (iii) x−1/2, −y+1/2, z−1/2; (iv) −x, −y+1, −z; (v) −x−1, −y+1, −z; (vi) −x+1/2, y+1/2, −z+1/2; (vii) x−1/2, −y+1/2, z+1/2; (viii) x+1/2, −y+3/2, z+1/2; (ix) x−1/2, −y+3/2, z−1/2; (x) −x−1/2, y+1/2, −z−1/2; (xi) −x, −y, −z; (xii) −x−1/2, y−1/2, −z−1/2; (xiii) x+1/2, −y+1/2, z−1/2; (xiv) −x+1, −y, −z; (xv) −x+1/2, y−1/2, −z+1/2; (xvi) −x−1/2, y+1/2, −z+1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O20.861.812.663 (2)173
N6′—H6A′···O3xv0.862.062.867 (2)156
N6′—H6B′···O10.862.092.929 (2)166
N2—H2A···O30.861.952.781 (2)163
N2—H2B···O1′i0.862.272.991 (2)141
N3—H3···O1′i0.861.972.775 (2)155
N3′—H3′···O6xii0.862.343.056 (2)141
N4′—H4A′···N5′xiv0.862.233.071 (2)165
N4′—H4B′···O7xii0.862.563.355 (2)154
N4′—H4B′···O3xiii0.862.533.136 (2)129
N6—H6A···O1′0.862.102.916 (2)157
C7—H7A···O10.972.552.930 (2)103
C7—H7B···O1′0.972.552.925 (2)103
Symmetry codes: (i) x+1/2, −y+1/2, z+1/2; (xii) −x−1/2, y−1/2, −z−1/2; (xiii) x+1/2, −y+1/2, z−1/2; (xiv) −x+1, −y, −z; (xv) −x+1/2, y−1/2, −z+1/2.

Experimental details

Crystal data
Chemical formulaC9H13N8O2+·C7H3N2O6−
Mr476.39
Crystal system, space groupMonoclinic, P21/n
Temperature (K)293
a, b, c (Å)7.365 (2), 19.788 (3), 13.658 (2)
β (°) 92.70 (2)
V (Å3)1988.3 (7)
Z4
Radiation typeMo Kα
µ (mm−1)0.13
Crystal size (mm)0.16 × 0.13 × 0.11
Data collection
DiffractometerBruker SMART CCD
Absorption correction–
No. of measured, independent and
observed [I > 2σ(I)] reflections		14081, 4216, 3046
Rint0.027
(sin θ/λ)max (Å−1)0.660
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.044, 0.129, 1.03
No. of reflections4216
No. of parameters307
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.30, −0.20

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O20.861.812.663 (2)173
N6'—H6A'···O3i0.862.062.867 (2)156
N6'—H6B'···O10.862.092.929 (2)166
N2—H2A···O30.861.952.781 (2)163
N2—H2B···O1'ii0.862.272.991 (2)141
N3—H3···O1'ii0.861.972.775 (2)155
N3'—H3'···O6iii0.862.343.056 (2)141
N4'—H4A'···N5'iv0.862.233.071 (2)165
N4'—H4B'···O7iii0.862.563.355 (2)154
N4'—H4B'···O3v0.862.533.136 (2)129
N6—H6A···O1'0.862.102.916 (2)157
C7—H7A···O10.972.552.930 (2)103
C7—H7B···O1'0.972.552.925 (2)103
Symmetry codes: (i) −x+1/2, y−1/2, −z+1/2; (ii) x+1/2, −y+1/2, z+1/2; (iii) −x−1/2, y−1/2, −z−1/2; (iv) −x+1, −y, −z; (v) x+1/2, −y+1/2, z−1/2.
 

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