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In the title crystal, trimethoprim perchlorate [2,4-di­amino-5-(3,4,5-tri­methoxy­benzyl)­pyrimidin-1-ium perchlorate], C14H19N4O3+·ClO4, the trimethoprim mol­ecule is protonated at N1. The perchlorate ion makes double hydrogen bonds of type N—H...O with the 2-amino group and the protonated N1 atom of the trimethoprim cation, reminiscent of the fork-like interactions of the carboxyl­ate group with the trimethoprim (TMP) cation observed in the di­hydro­folate reductase–trimethoprim complex. The pyrimidine moieties of trimethoprim cations are centrosymmetrically paired through a pair of N—H...N hydrogen bonds involving the 4-amino group and the pyrimidinium-N atom. The two pairs of TMP cations are linked by N—H...O hydrogen bonds to form a supramolecular ladder-like structure. The pyrimidine plane makes a dihedral angle of 83.72 (8)° with the phenyl ring in the TMP cation.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536801020293/ci6080sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536801020293/ci6080Isup2.hkl
Contains datablock I

CCDC reference: 180547

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.048
  • wR factor = 0.168
  • Data-to-parameter ratio = 21.4

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

General Notes

FORMU_01 There is a discrepancy between the atom counts in the _chemical_formula_sum and _chemical_formula_moiety. This is usually due to the moiety formula being in the wrong format. Atom count from _chemical_formula_sum: C14 H19 Cl1 N4 O7 Atom count from _chemical_formula_moiety:C14 H19 Cl1 N4 O4

Comment top

Trimethoprim (TMP) is a well known antifolate drug, which selectively inhibits the bacterial species of the enzyme dihydrofolate reductase (DHFR) (Hitching et al., 1988). This enzyme is found in bacteria and mammals. TMP and other antifolate drugs complexed with DHFR from various sources have been widely studied and are of current interest (Feeney, 2000). The N1-protonated diaminopyrimidine ring of TMP binds deep inside the enzyme cleft through several hydrogen bonds. The crystal structures of TMP and its complexes have been reported in the literature (Koetzle & Williams, 1976; Giuseppetti et al., 1984; Bryan et al., 1987; Bettinetti & Sardone, 1997). As part of structural investigations on drugs and their complexes in a variety of molecular environments carried out in our laboratory, we have reported the structures of trimethoprim formate (Umadevi & Muthiah, 1994), trimethoprim salicylate monohydrate (Murugesan & Muthiah, 1996), trimethoprim nitrate (Murugesan & Muthiah, 1997), trimethoprim hydrogen maleate (Prabakaran et al., 2001), trimethoprim glutarate (Robert et al., 2001) and trimethoprim sulfate trihydrate (Muthiah et al., 2001). The present study has been aimed at understanding the conformation and hydrogen bonding interactions in trimethoprim perchlorate, (I).

In the crystal structure of trimethoprim perchlorate (TMPP), the perchlorate ion is tetrahedral in shape as expected, with Cl—O distances ranging from 1.372 (2) to 1.431 (2) Å (Yokota et al., 1999). Small deviations from ideal values can be attributed to the relatively high temperature factors of the atoms in the perchlorate anion. The TMP is protonated at N1, as reported in various crystal structures containing TMP cations (Prabakaran et al., 2001). This is evident from the increase in the ring angle at the site of protonation, namely N1. The internal angle at N1, C2—N1—C6 has increased to 120.10 (14)°, as compared with 115.46° in neutral TMP (Koetzle & Williams, 1976). The conformation of the TMP molecule is described by two torsion angles, i.e. C4—C5—C7—C8 of 78.4 (2) and C5—C7—C8—C9 of -157.51 (1)°. These values are in the range reported for TMP sulfate trihydrate (Muthiah et al., 2001). The pyrimidine ring makes a dihedral angle of 83.72 (8)° with the phenyl ring, which is close to the value of 85.5 (2)° observed for trimethoprim sulfate trihydrate (Muthiah et al., 2001). An ORTEPIII (Farrugia, 1997) diagram of the molecule with the atom-labelling scheme is shown in Fig. 1.

The TMP cation and the perchlorate anion are linked by hydrogen bonds N1—H···O2 (of perchlorate ion) and N2—H···O3 (of the same perchlorate ion). This is reminiscent of the fork-like interaction of the carboxylate group (of Asp27 of the enzyme) with the TMP cation (Kuyper, 1990). The pyrimidine moieties of the trimethoprim cations are centrosymmetrically paired through a pair of N—H···N hydrogen bonds involving the 4-amino group and the pyrimidinium N3 atom. This type of pairing has also been reported in trimethoprim hydrogen maleate (Prabakaran et al., 2001) and trimethoprim sulfate trihydrate (Muthiah et al., 2001). The two pairs of TMP cations are linked by N2—H···O5 and N4—H···O5 hydrogen bonds to form a supramolecular ladder-like structure. These interactions are shown in Fig. 2. In addition, C—H···O hydrogen bonds also stabilize the crystal structure.

Experimental top

Trimethoprim perchlorate was prepared by dissolving trimethoprim (obtained as a gift from Shilpa Antibiotics Ltd) in hot methanol, followed by addition of dilute perchloric acid. On cooling, colourless crystals were formed.

Refinement top

After checking their presence in the difference map, the H-atoms were geometrically fixed and allowed to ride on their parent atoms.

Computing details top

Data collection: AED (Belletti et al., 1993); cell refinement: AED; data reduction: AED; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Farrugia, 1997); software used to prepare material for publication: PLATON (Spek, 1997).

Figures top
[Figure 1] Fig. 1. View of the title compound with the atom numbering scheme. Displacement ellipsoids for non-H atoms are drawn at the 50% probability level.
[Figure 2] Fig. 2. Hydrogen bonding-patterns in trimethoprim perchlorate
(I) top
Crystal data top
C14H19N4O3+·ClO41Z = 2
Mr = 390.78F(000) = 408
Triclinic, P1Dx = 1.498 Mg m3
a = 9.672 (2) ÅMo Kα radiation, λ = 0.71069 Å
b = 10.219 (1) ÅCell parameters from 25 reflections
c = 9.651 (2) Åθ = 3.1–30.2°
α = 91.19 (1)°µ = 0.27 mm1
β = 107.18 (1)°T = 293 K
γ = 72.44 (2)°Needle, colourless
V = 866.4 (3) Å30.3 × 0.3 × 0.2 mm
Data collection top
Siemens AED
diffractometer
θmax = 30.2°, θmin = 3.0°
ω–2θ scansh = 1313
5105 measured reflectionsk = 1414
5105 independent reflectionsl = 013
3593 reflections with I > 2σ(I)4 standard reflections every 60 min
Rint = 0.000 intensity decay: none
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)] = 0.048Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.168H-atom parameters constrained
S = 1.13 w = 1/[σ2(Fo2) + (0.1P)2]
where P = (Fo2 + 2Fc2)/3
5105 reflections(Δ/σ)max = 0.001
238 parametersΔρmax = 0.50 e Å3
0 restraintsΔρmin = 0.55 e Å3
Crystal data top
C14H19N4O3+·ClO41γ = 72.44 (2)°
Mr = 390.78V = 866.4 (3) Å3
Triclinic, P1Z = 2
a = 9.672 (2) ÅMo Kα radiation
b = 10.219 (1) ŵ = 0.27 mm1
c = 9.651 (2) ÅT = 293 K
α = 91.19 (1)°0.3 × 0.3 × 0.2 mm
β = 107.18 (1)°
Data collection top
Siemens AED
diffractometer
Rint = 0.000
5105 measured reflections4 standard reflections every 60 min
5105 independent reflections intensity decay: none
3593 reflections with I > 2σ(I)
Refinement top
R[F2 > 2σ(F2)] = 0.0480 restraints
wR(F2) = 0.168H-atom parameters constrained
S = 1.13Δρmax = 0.50 e Å3
5105 reflectionsΔρmin = 0.55 e Å3
238 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

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cl10.58921 (5)0.22357 (5)0.74380 (5)0.0417 (2)
O10.5842 (3)0.2534 (3)0.8818 (2)0.1382 (12)
O20.44393 (17)0.21975 (16)0.65308 (19)0.0536 (5)
O30.70113 (19)0.09439 (18)0.74596 (19)0.0680 (6)
O40.6244 (3)0.3261 (3)0.6778 (4)0.1223 (12)
O50.22609 (14)0.66522 (13)0.88174 (14)0.0355 (4)
O60.07301 (16)0.78921 (12)0.77103 (15)0.0408 (4)
O70.14090 (15)0.64527 (13)0.65037 (16)0.0398 (4)
N10.28807 (16)0.00692 (14)0.54264 (15)0.0305 (4)
N20.53292 (18)0.15022 (17)0.63999 (17)0.0436 (5)
N30.40806 (16)0.03135 (14)0.79476 (14)0.0299 (4)
N40.28624 (18)0.09237 (17)0.94650 (16)0.0415 (5)
C20.40918 (18)0.06260 (16)0.66056 (17)0.0281 (4)
C40.28321 (18)0.06162 (16)0.81173 (17)0.0267 (4)
C50.15019 (17)0.12401 (15)0.69077 (17)0.0253 (4)
C60.15972 (18)0.08500 (16)0.55881 (18)0.0288 (4)
C70.00703 (18)0.22108 (16)0.70981 (19)0.0299 (4)
C80.00386 (17)0.36849 (16)0.73827 (17)0.0256 (4)
C90.10110 (18)0.44362 (16)0.80645 (17)0.0273 (4)
C100.12333 (17)0.58342 (16)0.81887 (17)0.0268 (4)
C110.04072 (19)0.64888 (16)0.76584 (18)0.0291 (4)
C120.06679 (19)0.57224 (17)0.70101 (18)0.0292 (4)
C130.08899 (18)0.43152 (16)0.68792 (18)0.0282 (4)
C140.3212 (2)0.6021 (2)0.9278 (3)0.0458 (7)
C150.0414 (3)0.8336 (2)0.8714 (3)0.0524 (7)
C160.2759 (3)0.5701 (2)0.6172 (3)0.0553 (8)
H10.292140.029610.457290.0365*
H2A0.611740.186410.713190.0523*
H2B0.534320.170830.553460.0523*
H4A0.365680.053331.018080.0498*
H4B0.208770.151370.962350.0498*
H60.076750.121700.476950.0345*
H7A0.013560.182980.790020.0358*
H7B0.075980.223280.622870.0358*
H90.155780.400010.843330.0327*
H130.160940.380610.645390.0338*
H14A0.376060.563200.846640.0687*
H14B0.392010.670280.964170.0687*
H14C0.259030.530801.003180.0687*
H15A0.075380.780430.962760.0786*
H15B0.000330.929220.885350.0786*
H15C0.125680.821310.833970.0786*
H16A0.345550.510700.700400.0829*
H16B0.322340.633170.591980.0829*
H16C0.250780.515820.536710.0829*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0327 (2)0.0445 (3)0.0473 (3)0.0095 (2)0.0150 (2)0.0205 (2)
O10.0950 (17)0.201 (3)0.0562 (13)0.0274 (18)0.0101 (12)0.0673 (16)
O20.0370 (8)0.0556 (9)0.0673 (10)0.0171 (7)0.0120 (7)0.0114 (8)
O30.0522 (10)0.0651 (11)0.0622 (10)0.0149 (8)0.0161 (8)0.0181 (9)
O40.0676 (14)0.0830 (16)0.224 (3)0.0383 (13)0.0374 (17)0.0263 (18)
O50.0327 (6)0.0309 (6)0.0397 (7)0.0009 (5)0.0178 (5)0.0106 (5)
O60.0450 (8)0.0204 (6)0.0487 (8)0.0011 (5)0.0116 (6)0.0053 (5)
O70.0388 (7)0.0276 (6)0.0561 (8)0.0065 (5)0.0226 (6)0.0007 (5)
N10.0314 (7)0.0321 (7)0.0235 (7)0.0028 (6)0.0094 (5)0.0068 (5)
N20.0358 (8)0.0488 (10)0.0313 (8)0.0101 (7)0.0126 (6)0.0078 (7)
N30.0290 (7)0.0282 (7)0.0250 (7)0.0030 (5)0.0094 (5)0.0025 (5)
N40.0366 (8)0.0466 (9)0.0271 (7)0.0070 (7)0.0094 (6)0.0087 (6)
C20.0296 (8)0.0244 (7)0.0272 (8)0.0020 (6)0.0106 (6)0.0045 (6)
C40.0276 (8)0.0222 (7)0.0277 (8)0.0023 (6)0.0101 (6)0.0045 (6)
C50.0231 (7)0.0189 (7)0.0310 (8)0.0027 (5)0.0081 (6)0.0040 (6)
C60.0246 (7)0.0263 (7)0.0286 (8)0.0022 (6)0.0039 (6)0.0022 (6)
C70.0235 (7)0.0229 (7)0.0409 (9)0.0029 (6)0.0109 (7)0.0049 (7)
C80.0209 (7)0.0223 (7)0.0280 (8)0.0008 (5)0.0053 (6)0.0032 (6)
C90.0235 (7)0.0247 (7)0.0305 (8)0.0022 (6)0.0089 (6)0.0034 (6)
C100.0220 (7)0.0251 (7)0.0255 (7)0.0022 (6)0.0059 (6)0.0051 (6)
C110.0297 (8)0.0204 (7)0.0302 (8)0.0009 (6)0.0061 (6)0.0029 (6)
C120.0272 (8)0.0248 (7)0.0309 (8)0.0026 (6)0.0075 (6)0.0000 (6)
C130.0237 (7)0.0233 (7)0.0340 (8)0.0006 (6)0.0106 (6)0.0044 (6)
C140.0434 (11)0.0443 (11)0.0539 (12)0.0062 (9)0.0289 (10)0.0109 (9)
C150.0716 (16)0.0361 (10)0.0509 (12)0.0245 (10)0.0133 (11)0.0121 (9)
C160.0375 (11)0.0499 (12)0.0804 (17)0.0062 (9)0.0274 (11)0.0094 (11)
Geometric parameters (Å, º) top
Cl1—O11.372 (2)C5—C61.347 (2)
Cl1—O21.4309 (19)C7—C81.518 (2)
Cl1—O31.4284 (19)C8—C91.399 (2)
Cl1—O41.411 (3)C8—C131.378 (3)
O5—C101.374 (2)C9—C101.387 (2)
O5—C141.439 (3)C10—C111.388 (3)
O6—C111.376 (2)C11—C121.400 (3)
O6—C151.421 (3)C12—C131.397 (2)
O7—C121.362 (2)C6—H60.93
O7—C161.424 (3)C7—H7A0.97
N1—C21.352 (2)C7—H7B0.97
N1—C61.361 (2)C9—H90.93
N2—C21.327 (3)C13—H130.93
N3—C21.330 (2)C14—H14A0.96
N3—C41.344 (2)C14—H14B0.96
N4—C41.326 (2)C14—H14C0.96
N1—H10.86C15—H15A0.96
N2—H2A0.86C15—H15B0.96
N2—H2B0.86C15—H15C0.96
N4—H4B0.86C16—H16A0.96
N4—H4A0.86C16—H16B0.96
C4—C51.440 (2)C16—H16C0.96
C5—C71.500 (2)
Cl1···H16A3.1039C10···H2Aiv2.8386
Cl1···H1i2.9657C12···H14Cv2.9196
Cl1···H2Bi2.8719C12···H15C2.9592
O2···C23.009 (2)C13···H16C2.7450
O2···N13.135 (2)C13···H16A2.8032
O2···N33.088 (2)C13···H14Cv3.0296
O2···C63.322 (3)C14···H2Aiv2.8157
O2···C43.224 (3)C14···H4Bv3.0845
O2···C53.386 (3)C14···H92.4892
O2···N2i2.958 (2)C16···H132.5612
O3···N1i2.929 (2)C16···H7Bvi2.9425
O3···O6ii3.188 (2)H1···H2B2.2721
O4···C9iii3.154 (4)H1···Cl1i2.9657
O5···N2iv2.958 (2)H1···O3i2.0702
O5···N4v2.958 (2)H2A···O5ii2.1367
O5···O62.657 (2)H2A···O6ii2.8658
O6···O72.705 (2)H2A···C10ii2.8386
O6···O3iv3.188 (2)H2A···C14ii2.8157
O6···O52.657 (2)H2B···H12.2721
O6···C6vi3.230 (2)H2B···Cl1i2.8719
O7···O62.705 (2)H2B···O2i2.1001
O7···C153.017 (3)H4A···N3viii2.3425
O1···H14Bv2.6425H4B···C72.5844
O2···H2Bi2.1001H4B···C82.9226
O2···H132.7147H4B···H7A2.2327
O2···H16A2.9064H4B···O5v2.3934
O3···H1i2.0702H4B···C14v3.0845
O3···H15Bii2.8072H6···H7B2.3422
O4···H16A2.8532H6···O6vi2.5646
O4···H16Bvii2.8608H6···O7vi2.6797
O4···H9iii2.5603H7A···N42.7198
O4···H14Aiii2.8913H7A···H4B2.2327
O5···H4Bv2.3934H7A···H92.3676
O5···H2Aiv2.1367H7B···H62.3422
O6···H6vi2.5646H7B···O7vi2.7951
O6···H2Aiv2.8658H7B···C16vi2.9425
O7···H15C2.5019H9···O4ix2.5603
O7···H6vi2.6797H9···C142.4892
O7···H7Bvi2.7951H9···H7A2.3676
N1···O23.135 (2)H9···H14A2.2837
N1···O3i2.929 (2)H9···H14C2.2765
N2···O5ii2.958 (2)H9···H15Av2.4342
N2···O2i2.958 (2)H13···O22.7147
N3···O23.088 (2)H13···C52.7051
N3···N4viii3.155 (2)H13···C162.5612
N4···O5v2.958 (2)H13···H16A2.4658
N4···C83.436 (2)H13···H16C2.2555
N4···C14v3.402 (3)H14A···O4ix2.8913
N4···N3viii3.155 (2)H14A···C92.7102
N3···H4Aviii2.3425H14A···H92.2837
N4···H7A2.7198H14B···O1v2.6425
N4···H14Bv2.9261H14B···N4v2.9261
C2···O23.009 (2)H14C···C92.7484
C4···O23.224 (3)H14C···H92.2765
C5···O23.386 (3)H14C···C12v2.9196
C6···O23.322 (3)H14C···C13v3.0296
C6···O6vi3.230 (2)H15A···H9v2.4342
C8···N43.436 (2)H15B···O3iv2.8072
C9···O4ix3.154 (4)H15C···O72.5019
C9···C10v3.593 (2)H15C···C122.9592
C10···C9v3.593 (2)H16A···Cl13.1039
C14···N4v3.402 (3)H16A···O22.9064
C15···O73.017 (3)H16A···O42.8532
C5···H132.7051H16A···C132.8032
C7···H4B2.5844H16A···H132.4658
C8···H16Cvi3.0031H16B···O4vii2.8608
C8···H4B2.9226H16C···C132.7450
C9···H14C2.7484H16C···H132.2555
C9···H14A2.7102H16C···C8vi3.0031
O1—Cl1—O2110.64 (15)O6—C11—C12121.61 (17)
O1—Cl1—O3110.85 (14)C10—C11—C12119.40 (15)
O1—Cl1—O4111.12 (19)O6—C11—C10118.89 (16)
O2—Cl1—O3109.32 (11)O7—C12—C11115.34 (15)
O2—Cl1—O4106.33 (16)C11—C12—C13120.23 (17)
O3—Cl1—O4108.45 (15)O7—C12—C13124.40 (17)
C10—O5—C14117.13 (14)C8—C13—C12119.74 (16)
C11—O6—C15115.22 (15)N1—C6—H6119.27
C12—O7—C16117.66 (15)C5—C6—H6119.27
C2—N1—C6120.10 (14)C5—C7—H7A107.93
C2—N3—C4118.22 (14)C5—C7—H7B107.93
C2—N1—H1119.95C8—C7—H7A107.93
C6—N1—H1119.94C8—C7—H7B107.93
C2—N2—H2A120.00H7A—C7—H7B107.21
H2A—N2—H2B120.00C8—C9—H9120.12
C2—N2—H2B120.00C10—C9—H9120.12
H4A—N4—H4B120.00C8—C13—H13120.14
C4—N4—H4A120.00C12—C13—H13120.13
C4—N4—H4B120.00O5—C14—H14A109.44
N2—C2—N3119.58 (16)O5—C14—H14B109.45
N1—C2—N2118.24 (15)O5—C14—H14C109.48
N1—C2—N3122.18 (16)H14A—C14—H14B109.46
N3—C4—C5122.30 (14)H14A—C14—H14C109.49
N4—C4—C5120.80 (16)H14B—C14—H14C109.50
N3—C4—N4116.90 (15)O6—C15—H15A109.49
C4—C5—C6115.70 (15)O6—C15—H15B109.45
C6—C5—C7121.68 (15)O6—C15—H15C109.51
C4—C5—C7122.56 (14)H15A—C15—H15B109.43
N1—C6—C5121.47 (16)H15A—C15—H15C109.49
C5—C7—C8117.50 (15)H15B—C15—H15C109.45
C7—C8—C9116.97 (15)O7—C16—H16A109.50
C7—C8—C13122.37 (15)O7—C16—H16B109.47
C9—C8—C13120.37 (15)O7—C16—H16C109.47
C8—C9—C10119.75 (16)H16A—C16—H16B109.48
O5—C10—C9123.48 (16)H16A—C16—H16C109.48
O5—C10—C11116.05 (14)H16B—C16—H16C109.43
C9—C10—C11120.47 (16)
C14—O5—C10—C94.1 (2)C6—C5—C7—C8104.57 (19)
C14—O5—C10—C11175.49 (17)C5—C7—C8—C1328.5 (2)
C15—O6—C11—C10110.6 (2)C5—C7—C8—C9157.51 (15)
C15—O6—C11—C1273.2 (2)C13—C8—C9—C102.2 (2)
C16—O7—C12—C11164.60 (18)C7—C8—C13—C12171.72 (16)
C16—O7—C12—C1317.3 (3)C7—C8—C9—C10171.83 (15)
C6—N1—C2—N30.4 (3)C9—C8—C13—C122.0 (3)
C6—N1—C2—N2179.02 (16)C8—C9—C10—C110.9 (2)
C2—N1—C6—C50.8 (3)C8—C9—C10—O5178.75 (15)
C4—N3—C2—N11.9 (3)C9—C10—C11—O6175.61 (15)
C4—N3—C2—N2177.54 (17)O5—C10—C11—C12179.64 (15)
C2—N3—C4—N4178.96 (16)O5—C10—C11—O64.0 (2)
C2—N3—C4—C52.2 (3)C9—C10—C11—C120.7 (3)
N4—C4—C5—C6179.88 (17)O6—C11—C12—O72.9 (2)
N3—C4—C5—C7176.07 (16)O6—C11—C12—C13175.28 (16)
N3—C4—C5—C61.1 (2)C10—C11—C12—O7179.14 (16)
N4—C4—C5—C72.7 (3)C10—C11—C12—C131.0 (3)
C7—C5—C6—N1177.62 (16)O7—C12—C13—C8177.59 (16)
C4—C5—C6—N10.4 (2)C11—C12—C13—C80.4 (3)
C4—C5—C7—C878.4 (2)
Symmetry codes: (i) x+1, y, z+1; (ii) x+1, y1, z; (iii) x+1, y, z; (iv) x1, y+1, z; (v) x, y+1, z+2; (vi) x, y+1, z+1; (vii) x+1, y+1, z+1; (viii) x+1, y, z+2; (ix) x1, y, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O3i0.862.072.929 (2)176.7
N2—H2A···O5ii0.862.142.958 (2)159.7
N2—H2B···O2i0.862.102.958 (2)175.2
N4—H4A···N3viii0.862.343.155 (2)157.8
N4—H4B···O5v0.862.392.958 (2)123.7
C6—H6···O6vi0.932.563.230 (2)128.8
C9—H9···O4ix0.932.563.154 (4)122.1
C15—H15C···O70.962.503.017 (3)113.6
Symmetry codes: (i) x+1, y, z+1; (ii) x+1, y1, z; (v) x, y+1, z+2; (vi) x, y+1, z+1; (viii) x+1, y, z+2; (ix) x1, y, z.

Experimental details

Crystal data
Chemical formulaC14H19N4O3+·ClO41
Mr390.78
Crystal system, space groupTriclinic, P1
Temperature (K)293
a, b, c (Å)9.672 (2), 10.219 (1), 9.651 (2)
α, β, γ (°)91.19 (1), 107.18 (1), 72.44 (2)
V3)866.4 (3)
Z2
Radiation typeMo Kα
µ (mm1)0.27
Crystal size (mm)0.3 × 0.3 × 0.2
Data collection
DiffractometerSiemens AED
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
5105, 5105, 3593
Rint0.000
(sin θ/λ)max1)0.707
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.048, 0.168, 1.13
No. of reflections5105
No. of parameters238
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.50, 0.55

Computer programs: AED (Belletti et al., 1993), AED, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEPIII (Farrugia, 1997), PLATON (Spek, 1997).

Selected geometric parameters (Å, º) top
Cl1—O11.372 (2)O7—C121.362 (2)
Cl1—O21.4309 (19)O7—C161.424 (3)
Cl1—O31.4284 (19)N1—C21.352 (2)
Cl1—O41.411 (3)N1—C61.361 (2)
O5—C101.374 (2)N2—C21.327 (3)
O5—C141.439 (3)N3—C21.330 (2)
O6—C111.376 (2)N3—C41.344 (2)
O6—C151.421 (3)N4—C41.326 (2)
O1—Cl1—O2110.64 (15)N1—C2—N2118.24 (15)
O1—Cl1—O3110.85 (14)N1—C2—N3122.18 (16)
O1—Cl1—O4111.12 (19)N3—C4—C5122.30 (14)
O2—Cl1—O3109.32 (11)N4—C4—C5120.80 (16)
O2—Cl1—O4106.33 (16)N3—C4—N4116.90 (15)
O3—Cl1—O4108.45 (15)N1—C6—C5121.47 (16)
C10—O5—C14117.13 (14)O5—C10—C9123.48 (16)
C11—O6—C15115.22 (15)O5—C10—C11116.05 (14)
C12—O7—C16117.66 (15)O6—C11—C12121.61 (17)
C2—N1—C6120.10 (14)O6—C11—C10118.89 (16)
C2—N3—C4118.22 (14)O7—C12—C11115.34 (15)
N2—C2—N3119.58 (16)O7—C12—C13124.40 (17)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O3i0.862.072.929 (2)176.7
N2—H2A···O5ii0.862.142.958 (2)159.7
N2—H2B···O2i0.862.102.958 (2)175.2
N4—H4A···N3iii0.862.343.155 (2)157.8
N4—H4B···O5iv0.862.392.958 (2)123.7
C6—H6···O6v0.932.563.230 (2)128.8
C9—H9···O4vi0.932.563.154 (4)122.1
C15—H15C···O70.962.503.017 (3)113.6
Symmetry codes: (i) x+1, y, z+1; (ii) x+1, y1, z; (iii) x+1, y, z+2; (iv) x, y+1, z+2; (v) x, y+1, z+1; (vi) x1, y, z.
 

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