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In the title compound [systematic name: 2,4-diamino-5-(3,4,5-trimethoxy­benz­yl)pyrimidinium 2-hydr­oxy-3,5-dinitro­benzoate], C14H19N4O3+·C7H3N2O7, the trimethoprimium (TMP) cation is protonated at one of the pyrimidine N atoms. The protonated N atom and the 2-amino group of the TMP cation inter­act with the carboxyl­ate group of the 3,5-dinitro­salicylate anion through a pair of N—H...O hydrogen bonds. A typical intra­molecular O—H...O hydrogen bond is observed in the anion.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680704189X/hb2509sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680704189X/hb2509Isup2.hkl
Contains datablock I

CCDC reference: 663760

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.015 Å
  • R factor = 0.064
  • wR factor = 0.152
  • Data-to-parameter ratio = 6.6

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT026_ALERT_3_B Ratio Observed / Unique Reflections too Low .... 39 Perc. PLAT340_ALERT_3_B Low Bond Precision on C-C Bonds (x 1000) Ang ... 15
Alert level C PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) ..... 6.64 PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.95 Ratio PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.47 Ratio PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for O1 PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 2 C7 H3 N2 O7
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 70.20 From the CIF: _reflns_number_total 2244 Count of symmetry unique reflns 2278 Completeness (_total/calc) 98.51% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 0 Fraction of Friedel pairs measured 0.000 Are heavy atom types Z>Si present no PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 1
0 ALERT level A = In general: serious problem 2 ALERT level B = Potentially serious problem 5 ALERT level C = Check and explain 4 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 ALERT type 2 Indicator that the structure model may be wrong or deficient 5 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

As part of our ongoing studies (Hemamalini et al., 2005) of hydrogen bonding patterns in the molecular salts of protonated trimethoprim [2,4-diamino-5-(3,4,5-trimethoxybenzyl-pyrimidine or TMP], we now report the synthesis and structure of the title compound, (I). [systematic name: 2,4-diamino-5-(3,4,5-trimethoxybenzyl) pyrimidin-1-ium 2-hydroxy-3,5-dinitrobenzoate]. Neutral TMP is a well known antifolate drug and its structure was determined by Koetzle & Williams (1976).

The asymmetric unit of (I) contains a protonated TMP cation and a 3,5-dinitrosalicylate (DNSA) anion (Fig. 1). The trimethoprim molecule is protonated at atom N1 of the pyrimidine moiety, which is evident from the increase in the internal angle at the protonated N1 [C2—N1—C6 = 121.7 (10)°] compared with that at unprotonated atom N3 [C2—N3—C4 = 117.9 (9)°]. The dihedral angle between the pyrimidine and benzene ring planes in (I) is 72.48 (5)°, which falls within the known range of equivalent torsion angles [69.96 (8)–89.5 (2)°] in other TMP structures (Panneerselvam et al., 2002). The conformation of the TMP cation is described by the two torsion angles C4—C5—C7—C8 and C5—C7—C8—C9, which are -176.0 (9)° and 69.9 (13)°, respectively in (I). This TMP conformation plays a very important role in DHFR selectivity (Hitching et al., 1988).

The carboxylate group of the DNSA anion in (I) accepts two N—H···O hydrogen bonds (Table 1) from the cation, forming a fork-like interaction. This can be designated by graph-set notation R22(8) (Bernstein et al., 1995). This common motif has been observed in other DHFR-TMP complexes (Kuyper, 1990) A typical intramolecular hydrogen bond occurs in the anion with graph-set notation S(6) (Fig. 2). The TMP cations self assemble via further N—H···O interactions, with the O atom being part of a methoxy or a nitro group. The combination of hydrogen bonds forms a three dimensional network as shown in Fig 3.

Related literature top

For related literature, see: Bernstein et al. (1995); Hemamalini et al. (2005); Hitching et al. (1988); Koetzle & Williams (1976); Kuyper (1990); Panneerselvam et al. (2002).

Experimental top

Hot methanol solutions of trimethoprim (74 mg, obtained as a gift from Shilpa Antibiotics Ltd) and 3,5-dinitrosalicylic acid (57 mg, Merck) were mixed in a 1:1 molar ratio and warmed for half an hour over a water bath. On slow evaporation, yellow prisms of (I) were obtained.

Refinement top

All the hydrogen atoms were placed in idealized locations (C—H = 0.96 Å, O—H = 0.82 Å, N—H = 0.86 Å) and refined as riding with Uiso(H) = 1.2Ueq(carrier) or 1.5Ueq(methyl carrier).

Structure description top

As part of our ongoing studies (Hemamalini et al., 2005) of hydrogen bonding patterns in the molecular salts of protonated trimethoprim [2,4-diamino-5-(3,4,5-trimethoxybenzyl-pyrimidine or TMP], we now report the synthesis and structure of the title compound, (I). [systematic name: 2,4-diamino-5-(3,4,5-trimethoxybenzyl) pyrimidin-1-ium 2-hydroxy-3,5-dinitrobenzoate]. Neutral TMP is a well known antifolate drug and its structure was determined by Koetzle & Williams (1976).

The asymmetric unit of (I) contains a protonated TMP cation and a 3,5-dinitrosalicylate (DNSA) anion (Fig. 1). The trimethoprim molecule is protonated at atom N1 of the pyrimidine moiety, which is evident from the increase in the internal angle at the protonated N1 [C2—N1—C6 = 121.7 (10)°] compared with that at unprotonated atom N3 [C2—N3—C4 = 117.9 (9)°]. The dihedral angle between the pyrimidine and benzene ring planes in (I) is 72.48 (5)°, which falls within the known range of equivalent torsion angles [69.96 (8)–89.5 (2)°] in other TMP structures (Panneerselvam et al., 2002). The conformation of the TMP cation is described by the two torsion angles C4—C5—C7—C8 and C5—C7—C8—C9, which are -176.0 (9)° and 69.9 (13)°, respectively in (I). This TMP conformation plays a very important role in DHFR selectivity (Hitching et al., 1988).

The carboxylate group of the DNSA anion in (I) accepts two N—H···O hydrogen bonds (Table 1) from the cation, forming a fork-like interaction. This can be designated by graph-set notation R22(8) (Bernstein et al., 1995). This common motif has been observed in other DHFR-TMP complexes (Kuyper, 1990) A typical intramolecular hydrogen bond occurs in the anion with graph-set notation S(6) (Fig. 2). The TMP cations self assemble via further N—H···O interactions, with the O atom being part of a methoxy or a nitro group. The combination of hydrogen bonds forms a three dimensional network as shown in Fig 3.

For related literature, see: Bernstein et al. (1995); Hemamalini et al. (2005); Hitching et al. (1988); Koetzle & Williams (1976); Kuyper (1990); Panneerselvam et al. (2002).

Computing details top

Data collection: XSCANS (Siemens, 1994); cell refinement: XSCANS (Siemens, 1994); data reduction: XSCANS (Siemens, 1994); 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. The molecular structure of (I) showing 50% probability displacement ellipsoids for the non-hydrogen atoms.
[Figure 2] Fig. 2. Hydrogen bonding interactions of the title compound (I), (hydrogen atoms are omitted for clarity). Symmetry codes: (i) x + 1/2,-y,z; (ii) x + 1/2,-y + 2,z.
[Figure 3] Fig. 3. Packing of the title compound (I).
2,4-diamino-5-(3,4,5-trimethoxybenzyl)pyrimidinium 2-hydroxy-3,5-dinitrobenzoate top
Crystal data top
C14H19N4O3+·C7H3N2O7F(000) = 1080
Mr = 518.45Dx = 1.469 Mg m3
Orthorhombic, Pca21Cu Kα radiation, λ = 1.54178 Å
Hall symbol: P 2c -2acCell parameters from 26 reflections
a = 20.928 (3) Åθ = 4.7–70.2°
b = 4.898 (2) ŵ = 1.02 mm1
c = 22.869 (2) ÅT = 293 K
V = 2344.2 (10) Å3Prism, light yellow
Z = 40.16 × 0.12 × 0.06 mm
Data collection top
Siemens AED single-crystal
diffractometer
θmax = 70.2°, θmin = 4.7°
Radiation source: fine- focus sealed tubeh = 250
Graphite monochromatork = 50
ω–2θ scansl = 027
2244 measured reflections1 standard reflections every 100 reflections
2244 independent reflections intensity decay: none
883 reflections with I > 2σ(I)
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)] = 0.064Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.152H-atom parameters constrained
S = 0.92 w = 1/[σ2(Fo2) + (0.0456P)2]
where P = (Fo2 + 2Fc2)/3
2244 reflections(Δ/σ)max < 0.001
338 parametersΔρmax = 0.32 e Å3
1 restraintΔρmin = 0.21 e Å3
Crystal data top
C14H19N4O3+·C7H3N2O7V = 2344.2 (10) Å3
Mr = 518.45Z = 4
Orthorhombic, Pca21Cu Kα radiation
a = 20.928 (3) ŵ = 1.02 mm1
b = 4.898 (2) ÅT = 293 K
c = 22.869 (2) Å0.16 × 0.12 × 0.06 mm
Data collection top
Siemens AED single-crystal
diffractometer
883 reflections with I > 2σ(I)
2244 measured reflections1 standard reflections every 100 reflections
2244 independent reflections intensity decay: none
Refinement top
R[F2 > 2σ(F2)] = 0.0641 restraint
wR(F2) = 0.152H-atom parameters constrained
S = 0.92Δρmax = 0.32 e Å3
2244 reflectionsΔρmin = 0.21 e Å3
338 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
O10.4839 (3)0.9192 (16)0.0266 (3)0.057 (3)
O20.4526 (3)0.6666 (16)0.1250 (4)0.058 (3)
O30.5418 (3)0.474 (2)0.1986 (4)0.067 (3)
N10.7512 (4)0.4715 (19)0.0459 (4)0.046 (3)
N20.8415 (4)0.420 (2)0.1010 (4)0.059 (4)
N30.8398 (4)0.7382 (18)0.0286 (4)0.043 (3)
N40.8399 (4)1.0501 (19)0.0461 (4)0.046 (3)
C20.8108 (4)0.546 (3)0.0580 (5)0.045 (4)
C40.8083 (5)0.854 (2)0.0162 (5)0.037 (3)
C50.7455 (4)0.7855 (19)0.0311 (5)0.040 (4)
C60.7175 (5)0.590 (2)0.0023 (5)0.039 (4)
C70.7130 (5)0.917 (2)0.0841 (5)0.046 (4)
C80.6439 (5)0.834 (2)0.0912 (5)0.045 (4)
C90.5960 (5)0.919 (2)0.0531 (5)0.049 (4)
C100.5337 (5)0.849 (2)0.0627 (5)0.041 (4)
C110.5154 (5)0.708 (2)0.1126 (5)0.041 (3)
C120.5628 (5)0.616 (2)0.1511 (5)0.048 (4)
C130.6270 (4)0.683 (2)0.1406 (5)0.045 (4)
C140.4999 (7)1.075 (4)0.0227 (6)0.109 (8)
C150.4282 (6)0.397 (3)0.1137 (7)0.084 (6)
C160.5889 (7)0.331 (3)0.2285 (6)0.084 (6)
O40.6798 (4)0.0705 (17)0.0983 (3)0.060 (3)
O50.7609 (4)0.0101 (16)0.1597 (4)0.066 (3)
O60.7550 (4)0.337 (2)0.2374 (5)0.077 (4)
O70.7225 (5)0.608 (2)0.3338 (4)0.099 (4)
O80.6653 (4)0.961 (2)0.3140 (4)0.081 (4)
O90.4875 (4)0.821 (2)0.1826 (4)0.094 (4)
O100.4860 (4)0.473 (2)0.1288 (4)0.077 (4)
N50.6863 (5)0.730 (2)0.3025 (5)0.058 (4)
N60.5133 (5)0.621 (2)0.1634 (4)0.056 (3)
C170.6689 (4)0.266 (2)0.1725 (4)0.035 (3)
C180.6985 (5)0.400 (2)0.2211 (5)0.047 (4)
C190.6609 (5)0.602 (2)0.2491 (4)0.040 (4)
C200.6015 (5)0.662 (2)0.2316 (4)0.044 (4)
C210.5760 (5)0.542 (2)0.1837 (5)0.041 (3)
C220.6100 (5)0.337 (2)0.1543 (5)0.047 (4)
C230.7064 (5)0.043 (2)0.1412 (6)0.048 (4)
H10.733500.345100.066400.0560*
H2A0.880200.464500.109300.0710*
H2B0.822800.292900.120600.0710*
H4A0.878101.094700.036000.0550*
H4B0.821801.130300.075100.0550*
H60.675500.537000.004900.0470*
H7A0.715301.114000.080200.0550*
H7B0.736300.866700.119100.0550*
H90.606501.025300.020700.0580*
H130.658400.627200.166800.0540*
H14A0.533400.984900.043900.1630*
H14B0.463101.093800.047300.1630*
H14C0.514201.252000.010500.1630*
H15A0.455200.264500.132100.1250*
H15B0.385700.382500.129100.1250*
H15C0.427400.365400.072300.1250*
H16A0.619900.456300.243800.1260*
H16B0.569800.230400.260000.1260*
H16C0.609600.206100.202200.1260*
H6A0.760400.171900.233300.1160*
H200.577400.788300.252500.0530*
H220.591900.250100.122200.0570*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.035 (4)0.076 (6)0.060 (5)0.002 (4)0.000 (4)0.000 (5)
O20.040 (4)0.055 (5)0.079 (6)0.004 (4)0.017 (4)0.006 (5)
O30.049 (4)0.093 (7)0.058 (6)0.000 (5)0.014 (4)0.010 (6)
N10.044 (5)0.037 (5)0.058 (6)0.002 (5)0.008 (4)0.007 (5)
N20.040 (4)0.074 (7)0.064 (7)0.009 (5)0.009 (5)0.024 (7)
N30.033 (4)0.042 (6)0.054 (6)0.005 (5)0.005 (4)0.002 (5)
N40.028 (4)0.060 (7)0.050 (6)0.003 (5)0.002 (4)0.009 (6)
C20.018 (5)0.075 (9)0.043 (6)0.009 (6)0.007 (5)0.004 (7)
C40.029 (5)0.040 (7)0.041 (6)0.008 (5)0.004 (5)0.003 (6)
C50.030 (5)0.027 (6)0.062 (8)0.000 (5)0.011 (5)0.005 (6)
C60.032 (5)0.033 (7)0.052 (7)0.004 (5)0.005 (5)0.003 (6)
C70.046 (6)0.044 (7)0.049 (7)0.003 (6)0.012 (5)0.008 (6)
C80.042 (6)0.038 (7)0.054 (7)0.010 (5)0.015 (5)0.011 (6)
C90.038 (6)0.060 (8)0.048 (7)0.008 (6)0.004 (5)0.015 (7)
C100.041 (6)0.037 (6)0.046 (7)0.003 (5)0.002 (5)0.008 (6)
C110.038 (5)0.032 (6)0.054 (7)0.003 (5)0.016 (6)0.004 (6)
C120.054 (6)0.052 (7)0.039 (6)0.001 (6)0.010 (6)0.005 (7)
C130.033 (5)0.060 (8)0.042 (7)0.005 (6)0.008 (5)0.017 (6)
C140.077 (10)0.186 (19)0.064 (9)0.046 (12)0.004 (8)0.006 (12)
C150.063 (7)0.059 (9)0.129 (14)0.017 (7)0.024 (9)0.032 (10)
C160.092 (11)0.065 (10)0.095 (11)0.016 (9)0.037 (9)0.018 (9)
O40.071 (5)0.061 (6)0.048 (5)0.008 (5)0.005 (4)0.016 (5)
O50.053 (5)0.064 (6)0.082 (7)0.003 (5)0.018 (5)0.003 (6)
O60.058 (6)0.085 (7)0.089 (7)0.005 (5)0.007 (5)0.017 (7)
O70.151 (9)0.083 (7)0.063 (7)0.012 (7)0.050 (7)0.009 (6)
O80.091 (7)0.067 (7)0.085 (7)0.009 (6)0.002 (5)0.023 (6)
O90.079 (6)0.099 (7)0.103 (8)0.035 (6)0.013 (6)0.044 (7)
O100.072 (6)0.080 (7)0.078 (7)0.017 (6)0.028 (5)0.009 (6)
N50.077 (7)0.055 (7)0.043 (6)0.008 (6)0.006 (6)0.008 (6)
N60.053 (5)0.067 (7)0.047 (6)0.006 (6)0.000 (5)0.011 (6)
C170.038 (5)0.037 (7)0.030 (6)0.013 (5)0.005 (5)0.005 (5)
C180.034 (6)0.050 (8)0.058 (8)0.002 (6)0.003 (5)0.007 (7)
C190.045 (6)0.047 (7)0.029 (6)0.004 (6)0.006 (5)0.012 (6)
C200.046 (6)0.049 (7)0.038 (6)0.005 (6)0.002 (5)0.001 (6)
C210.042 (5)0.038 (7)0.042 (6)0.004 (5)0.010 (5)0.006 (6)
C220.058 (7)0.041 (7)0.042 (7)0.009 (6)0.009 (6)0.003 (6)
C230.039 (6)0.031 (7)0.073 (9)0.015 (5)0.019 (6)0.015 (7)
Geometric parameters (Å, º) top
O1—C101.373 (13)C7—C81.511 (15)
O1—C141.402 (17)C8—C131.396 (15)
O2—C111.360 (12)C8—C91.392 (15)
O2—C151.439 (16)C9—C101.366 (15)
O3—C121.363 (14)C10—C111.388 (16)
O3—C161.389 (17)C11—C121.401 (15)
O4—C231.258 (15)C12—C131.404 (14)
O5—C231.244 (14)C6—H60.9312
O6—C181.278 (14)C7—H7B0.9691
O7—N51.201 (15)C7—H7A0.9702
O8—N51.242 (14)C9—H90.9319
O9—N61.202 (14)C13—H130.9303
O10—N61.216 (13)C14—H14C0.9586
O6—H6A0.8219C14—H14A0.9599
N1—C61.352 (14)C14—H14B0.9582
N1—C21.329 (13)C15—H15C0.9595
N2—C21.327 (15)C15—H15A0.9579
N3—C41.344 (14)C15—H15B0.9593
N3—C21.306 (15)C16—H16A0.9592
N4—C41.352 (14)C16—H16B0.9600
N1—H10.8604C16—H16C0.9611
N2—H2B0.8612C17—C221.347 (14)
N2—H2A0.8599C17—C231.524 (14)
N4—H4A0.8603C17—C181.432 (14)
N4—H4B0.8589C18—C191.417 (14)
N5—C191.472 (15)C19—C201.339 (15)
N6—C211.445 (15)C20—C211.353 (15)
C4—C51.399 (14)C21—C221.402 (15)
C5—C61.358 (14)C20—H200.9303
C5—C71.532 (15)C22—H220.9293
C10—O1—C14116.0 (9)C8—C7—H7A108.96
C11—O2—C15116.3 (9)C5—C7—H7A108.87
C12—O3—C16114.9 (9)C5—C7—H7B108.86
C18—O6—H6A109.37H7A—C7—H7B107.69
C2—N1—C6121.7 (10)C10—C9—H9119.55
C2—N3—C4117.9 (9)C8—C9—H9119.67
C6—N1—H1119.08C8—C13—H13119.86
C2—N1—H1119.23C12—C13—H13119.82
C2—N2—H2A120.11O1—C14—H14C109.44
H2A—N2—H2B119.76O1—C14—H14B109.42
C2—N2—H2B120.13H14A—C14—H14C109.56
C4—N4—H4A119.95O1—C14—H14A109.29
H4A—N4—H4B120.07H14A—C14—H14B109.55
C4—N4—H4B119.99H14B—C14—H14C109.57
O7—N5—C19120.7 (10)H15A—C15—H15B109.60
O7—N5—O8123.4 (11)O2—C15—H15A109.48
O8—N5—C19115.8 (10)O2—C15—H15B109.33
O9—N6—O10120.8 (10)O2—C15—H15C109.35
O10—N6—C21118.4 (9)H15B—C15—H15C109.52
O9—N6—C21120.6 (9)H15A—C15—H15C109.54
N1—C2—N2118.8 (11)H16B—C16—H16C109.30
N2—C2—N3119.4 (9)O3—C16—H16B109.43
N1—C2—N3121.8 (10)O3—C16—H16C109.44
N3—C4—C5123.1 (10)H16A—C16—H16B109.65
N3—C4—N4116.5 (9)H16A—C16—H16C109.31
N4—C4—C5120.5 (10)O3—C16—H16A109.69
C6—C5—C7123.4 (9)C18—C17—C22121.2 (9)
C4—C5—C6116.0 (10)C18—C17—C23118.1 (8)
C4—C5—C7120.6 (9)C22—C17—C23120.8 (9)
N1—C6—C5119.5 (9)O6—C18—C19123.4 (10)
C5—C7—C8113.4 (9)C17—C18—C19115.5 (9)
C7—C8—C13118.2 (9)O6—C18—C17121.1 (10)
C7—C8—C9122.8 (10)N5—C19—C18118.1 (9)
C9—C8—C13118.9 (9)C18—C19—C20122.3 (9)
C8—C9—C10120.8 (10)N5—C19—C20119.3 (9)
O1—C10—C11114.2 (9)C19—C20—C21120.9 (9)
C9—C10—C11121.4 (10)N6—C21—C22119.9 (10)
O1—C10—C9124.4 (10)C20—C21—C22119.9 (10)
O2—C11—C12120.4 (10)N6—C21—C20120.1 (9)
C10—C11—C12118.8 (10)C17—C22—C21120.1 (10)
O2—C11—C10120.8 (10)O4—C23—C17117.1 (9)
C11—C12—C13119.7 (10)O5—C23—C17117.5 (10)
O3—C12—C11115.9 (9)O4—C23—O5125.4 (10)
O3—C12—C13124.4 (10)C19—C20—H20119.73
C8—C13—C12120.3 (9)C21—C20—H20119.41
C5—C6—H6120.30C17—C22—H22119.93
N1—C6—H6120.20C21—C22—H22119.99
C8—C7—H7B108.93
C14—O1—C10—C90.5 (16)C9—C8—C13—C120.7 (15)
C14—O1—C10—C11176.6 (11)C8—C9—C10—C114.6 (16)
C15—O2—C11—C1278.5 (14)C8—C9—C10—O1178.5 (10)
C15—O2—C11—C10103.5 (12)O1—C10—C11—C12177.2 (9)
C16—O3—C12—C1317.4 (16)C9—C10—C11—C125.6 (15)
C16—O3—C12—C11165.6 (10)O1—C10—C11—O24.8 (14)
C6—N1—C2—N30.3 (18)C9—C10—C11—O2172.4 (10)
C6—N1—C2—N2179.4 (10)O2—C11—C12—C13173.9 (9)
C2—N1—C6—C51.7 (16)C10—C11—C12—C134.1 (15)
C2—N3—C4—C52.5 (16)O2—C11—C12—O33.3 (15)
C2—N3—C4—N4179.3 (10)C10—C11—C12—O3178.7 (9)
C4—N3—C2—N2177.3 (10)C11—C12—C13—C81.8 (15)
C4—N3—C2—N12.3 (17)O3—C12—C13—C8178.7 (10)
O8—N5—C19—C18155.6 (10)C23—C17—C18—O60.8 (15)
O8—N5—C19—C2030.1 (14)C23—C17—C18—C19178.9 (9)
O7—N5—C19—C20146.2 (11)C18—C17—C22—C211.2 (15)
O7—N5—C19—C1828.1 (15)C23—C17—C22—C21179.8 (10)
O10—N6—C21—C2214.5 (15)C18—C17—C23—O4179.4 (10)
O10—N6—C21—C20164.4 (10)C22—C17—C18—O6178.3 (10)
O9—N6—C21—C22169.3 (10)C22—C17—C18—C192.0 (14)
O9—N6—C21—C2011.9 (16)C22—C17—C23—O5179.0 (10)
N3—C4—C5—C7177.7 (9)C22—C17—C23—O40.3 (15)
N4—C4—C5—C6178.7 (10)C18—C17—C23—O50.1 (15)
N4—C4—C5—C74.2 (15)O6—C18—C19—C20179.2 (11)
N3—C4—C5—C60.6 (15)O6—C18—C19—N55.0 (16)
C4—C5—C6—N11.4 (15)C17—C18—C19—N5174.7 (9)
C6—C5—C7—C87.2 (14)C17—C18—C19—C200.5 (15)
C4—C5—C7—C8176.0 (9)N5—C19—C20—C21178.1 (9)
C7—C5—C6—N1175.5 (9)C18—C19—C20—C214.0 (16)
C5—C7—C8—C13115.1 (11)C19—C20—C21—C224.9 (16)
C5—C7—C8—C969.9 (13)C19—C20—C21—N6176.3 (9)
C7—C8—C13—C12175.9 (9)N6—C21—C22—C17178.9 (10)
C13—C8—C9—C102.1 (15)C20—C21—C22—C172.3 (16)
C7—C8—C9—C10177.0 (10)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O40.861.902.743 (12)167
N2—H2A···O10i0.862.263.101 (12)166
N2—H2B···O50.862.102.946 (12)169
N4—H4A···O1ii0.862.233.050 (11)160
N4—H4B···O8iii0.862.593.202 (13)129
O6—H6A···O50.821.902.462 (14)124
C15—H15A···O30.962.583.093 (16)114
Symmetry codes: (i) x+1/2, y, z; (ii) x+1/2, y+2, z; (iii) x+3/2, y+2, z1/2.

Experimental details

Crystal data
Chemical formulaC14H19N4O3+·C7H3N2O7
Mr518.45
Crystal system, space groupOrthorhombic, Pca21
Temperature (K)293
a, b, c (Å)20.928 (3), 4.898 (2), 22.869 (2)
V3)2344.2 (10)
Z4
Radiation typeCu Kα
µ (mm1)1.02
Crystal size (mm)0.16 × 0.12 × 0.06
Data collection
DiffractometerSiemens AED single-crystal
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
2244, 2244, 883
Rint?
(sin θ/λ)max1)0.610
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.064, 0.152, 0.92
No. of reflections2244
No. of parameters338
No. of restraints1
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.32, 0.21

Computer programs: XSCANS (Siemens, 1994), 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···O40.861.902.743 (12)167
N2—H2A···O10i0.862.263.101 (12)166
N2—H2B···O50.862.102.946 (12)169
N4—H4A···O1ii0.862.233.050 (11)160
N4—H4B···O8iii0.862.593.202 (13)129
O6—H6A···O50.821.902.462 (14)124
C15—H15A···O30.962.583.093 (16)114
Symmetry codes: (i) x+1/2, y, z; (ii) x+1/2, y+2, z; (iii) x+3/2, y+2, z1/2.
 

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