Bis[8-ethyl-5-oxo-2-(piperazin-4-ium-1-yl)-5,8-dihydro­pyrido[2,3-d]pyrimidine-6-carb­oxy­lic acid] 2,5-dicarb­oxy­benzene-1,4-di­carboxyl­ate octa­hydrate

Zhang, G.-J.; He, J.-H.; Yan, S.-W.; Ye, Z.-L.; Xin, G.-H.

doi:10.1107/S1600536811011068

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 4| April 2011| Pages o1011-o1012

doi:10.1107/S1600536811011068

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Bis[8-ethyl-5-oxo-2-(piperazin-4-ium-1-yl)-5,8-dihydropyrido[2,3-d]pyrimidine-6-carboxylic acid] 2,5-dicarboxybenzene-1,4-dicarboxylate octahydrate

Guang-Ju Zhang,^a ^* Jiang-Hong He,^a Shi-Wei Yan,^a Zhong-Li Ye ^a and Guang-Hua Xin ^a

^aCollege of Chemistry and Chemical Engineering, Southwest University, Chongqing,400715, People's Republic of China
^*Correspondence e-mail: guaiguaijuzi@yahoo.com.cn

(Received 19 March 2011; accepted 25 March 2011; online 31 March 2011)

The asymmetric unit of the title compound, 2C₁₄H₁₈N₅O₃⁺·C₁₀H₅O₈²⁻·8H₂O, contains one [H₂ppa]⁺cation, one half of an [H₂btec]²⁻ anion (H₄btec = 1,2,4,5-benzenetetracarboxylic acid and Hppa = 8-ethyl-5-oxo-2-piperazin-1-yl-5,8-dihydropyrido[2,3-d]pyrimidine-6-carboxylic acid) that is completed by inversion symmetry and four water molecules. In the crystal, the molecules are connected by intermolecular hydrogen-bonding interactions and π–π stacking between the benzene rings of the [H₂btec]²⁻ anion and the pyrimidine rings of the [H₂ppa]⁺ cation [centroid–centroid distance = 3.597 (3) Å], generating a three-dimensional supramolecular structure.

Related literature

For general background to the use of quinolones in the treatment of infections, see: Mizuki et al. (1996 ).

Experimental

Crystal data

C₁₄H₁₈N₅O₃⁺·0.5C₁₀H₄O₈⁻·4H₂O
M_r = 502.46
Triclinic, $[P \overline 1]$
a = 8.8336 (16) Å
b = 11.103 (2) Å
c = 12.445 (2) Å
α = 83.010 (2)°
β = 76.737 (2)°
γ = 73.831 (2)°
V = 1138.9 (4) Å³
Z = 2
Mo Kα radiation
μ = 0.12 mm⁻¹
T = 296 K
0.52 × 0.48 × 0.39 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.940, T_max = 0.954
10252 measured reflections
5071 independent reflections
3550 reflections with I > 2σ(I)
R_int = 0.021

Refinement

R[F² > 2σ(F²)] = 0.046
wR(F²) = 0.160
S = 1.01
5071 reflections
352 parameters
14 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.33 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O6—H6A⋯O4ⁱ	0.92 (2)	1.47 (2)	2.392 (2)	178 (3)
N1—H1A⋯OW1ⁱⁱ	0.90	2.08	2.952 (2)	164
N1—H1A⋯O6ⁱⁱ	0.90	2.56	3.022 (2)	113
N1—H1B⋯OW2ⁱⁱ	0.90	1.82	2.717 (2)	176
OW1—HW1A⋯O1ⁱⁱⁱ	0.88 (2)	1.98 (2)	2.780 (2)	150 (2)
OW1—HW1B⋯O3	0.85 (2)	2.38 (2)	3.041 (2)	135 (2)
OW1—HW1B⋯O7	0.85 (2)	2.57 (2)	3.204 (2)	132 (2)
OW1—HW1B⋯O6	0.85 (2)	2.59 (2)	3.084 (2)	118 (2)
O2—H2A⋯O3	0.99 (2)	1.56 (2)	2.5013 (19)	159 (2)
OW2—HW2B⋯OW4^iv	0.86 (2)	1.86 (2)	2.703 (3)	168 (3)
OW2—HW2A⋯O5^iv	0.84 (2)	1.98 (2)	2.819 (2)	173 (3)
OW3—HW3A⋯OW1^v	0.85 (2)	1.93 (2)	2.770 (2)	169 (3)
OW3—HW3B⋯O2^vi	0.85 (2)	2.17 (2)	3.011 (3)	172 (3)
OW4—HW4A⋯O4^vii	0.87 (2)	1.94 (2)	2.782 (2)	163 (3)
OW4—HW4B⋯OW3	0.81 (2)	1.97 (2)	2.775 (3)	174 (3)
Symmetry codes: (i) -x, -y+2, -z+1; (ii) x, y, z-1; (iii) x+1, y, z; (iv) -x+1, -y+2, -z+1; (v) -x+1, -y+1, -z+1; (vi) x+1, y, z-1; (vii) -x+1, -y+2, -z.

Data collection: SMART (Bruker, 2001 ); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL-Plus (Sheldrick, 2008); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811011068/ff2005sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811011068/ff2005Isup2.hkl

checkCIF report

Comment top

Pipemidic acid (8-ethyl-5-oxo-2-piperazin-1-yl-5,8-dihydropyrido[2,3-d]pyrimidine-6- carboxylic acid) is member of quinolones used to treat infections (Mizuki et al., 1996). The complexes of the Hppa and H₄btec have not been reported till now. In this paper, the structure of the title compound, 1, is described (Fig. 1). The asymmetric unit contains one [H₂ppa]⁺cation, one half of [H₂btec]^2- anion that is completed by inversion symmetry, and four lattice water molecules. The molecules are linked by intermolecular N—H···O and O—H···O hydrogen-bonding interactions (N···O = 2.717 (2)–3.022 (2) Å, O···O = 2.392 (2)–3.204 (2) Å) and π—π stacking between the benzene rings of [H₂btec]^2- anion and the pyrimidine rings of [H₂ppa]⁺cation (centroid distance of 3.597 (3) Å) to form a three-dimensional supramolecular structure.

Related literature top

For general background to the use of quinolones in the treatment of infections, see: Mizuki et al. (1996).

Experimental top

A mixture of AgNO₃ (0.085 g, 0.5 mmol), Hppa (0.089 g, 0.25 mmol), H₄btec (0.064 g, 0.25 mmol) and distilled water (8 ml) was stirred for 20 min. in air. The mixture was then transferred to a 18 ml Teflon-lined hydrothermal bomb. The bomb was kept at 393 K for 96 h under autogenous pressure. Upon cooling, colorless blocks of 1 were obtained from the reaction mixture.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL-Plus (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

Fig. 1. The structure of 1. Displacement ellipsoids are drawn at the 30% probability level. H atoms have been omitted for clarity. [Symmetry code: -x,-y+2, -z+1].

Bis[8-ethyl-5-oxo-2-(piperazin-4-ium-1-yl)-5,8-dihydropyrido[2,3- d]pyrimidine-6-carboxylic acid] 2,5-dicarboxybenzene-1,4-dicarboxylate octahydrate top

Crystal data top

C₁₄H₁₈N₅O₃⁺·0.5C₁₀H₄O₈⁻·4H₂O	Z = 2
M_r = 502.46	F(000) = 530
Triclinic, P1	D_x = 1.465 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.8336 (16) Å	Cell parameters from 10252 reflections
b = 11.103 (2) Å	θ = 2.5–27.4°
c = 12.445 (2) Å	µ = 0.12 mm⁻¹
α = 83.010 (2)°	T = 296 K
β = 76.737 (2)°	Block, colourless
γ = 73.831 (2)°	0.52 × 0.48 × 0.39 mm
V = 1138.9 (4) Å³

Data collection top

Bruker APEX CCD area-detector diffractometer	5071 independent reflections
Radiation source: fine-focus sealed tube	3550 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.021
phi and ω scans	θ_max = 27.4°, θ_min = 2.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→11
T_min = 0.940, T_max = 0.954	k = −14→14
10252 measured reflections	l = −16→16

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.160	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ²(F_o²) + (0.1P)²] where P = (F_o² + 2F_c²)/3
5071 reflections	(Δ/σ)_max < 0.001
352 parameters	Δρ_max = 0.33 e Å⁻³
14 restraints	Δρ_min = −0.20 e Å⁻³

Crystal data top

C₁₄H₁₈N₅O₃⁺·0.5C₁₀H₄O₈⁻·4H₂O	γ = 73.831 (2)°
M_r = 502.46	V = 1138.9 (4) Å³
Triclinic, P1	Z = 2
a = 8.8336 (16) Å	Mo Kα radiation
b = 11.103 (2) Å	µ = 0.12 mm⁻¹
c = 12.445 (2) Å	T = 296 K
α = 83.010 (2)°	0.52 × 0.48 × 0.39 mm
β = 76.737 (2)°

Data collection top

Bruker APEX CCD area-detector diffractometer	5071 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3550 reflections with I > 2σ(I)
T_min = 0.940, T_max = 0.954	R_int = 0.021
10252 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	14 restraints
wR(F²) = 0.160	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	Δρ_max = 0.33 e Å⁻³
5071 reflections	Δρ_min = −0.20 e Å⁻³
352 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

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

	x	y	z	U_iso*/U_eq
C1	−0.2298 (2)	0.58949 (18)	0.76095 (14)	0.0453 (4)
C2	−0.1629 (2)	0.63420 (16)	0.64826 (13)	0.0362 (4)
C3	0.0071 (2)	0.60173 (15)	0.60569 (13)	0.0348 (4)
C4	0.05712 (18)	0.65003 (14)	0.49440 (12)	0.0316 (3)
C5	0.2186 (2)	0.62709 (16)	0.43913 (13)	0.0377 (4)
H5A	0.2968	0.5782	0.4765	0.045*
C6	0.14597 (19)	0.74223 (16)	0.28730 (13)	0.0336 (4)
C7	−0.05440 (18)	0.72426 (14)	0.43356 (12)	0.0295 (3)
C8	−0.2657 (2)	0.70738 (16)	0.58476 (13)	0.0360 (4)
H8A	−0.3755	0.7269	0.6149	0.043*
C9	−0.33740 (19)	0.83037 (17)	0.41760 (14)	0.0402 (4)
H9A	−0.2943	0.8957	0.3727	0.048*
H9B	−0.4340	0.8707	0.4687	0.048*
C10	−0.3799 (3)	0.7527 (2)	0.3443 (2)	0.0640 (6)
H10A	−0.4572	0.8056	0.3042	0.096*
H10B	−0.4251	0.6892	0.3887	0.096*
H10C	−0.2847	0.7134	0.2931	0.096*
C11	0.0817 (2)	0.85693 (19)	0.11400 (14)	0.0470 (4)
H11A	0.1022	0.9380	0.0881	0.056*
H11B	−0.0279	0.8712	0.1564	0.056*
C12	0.1010 (2)	0.78182 (19)	0.01646 (14)	0.0472 (5)
H12A	0.0685	0.7049	0.0421	0.057*
H12B	0.0317	0.8298	−0.0325	0.057*
C13	0.3844 (2)	0.68542 (19)	0.02854 (14)	0.0475 (5)
H13A	0.4945	0.6720	−0.0128	0.057*
H13B	0.3654	0.6040	0.0552	0.057*
C14	0.3613 (2)	0.7624 (2)	0.12515 (15)	0.0474 (5)
H14A	0.4303	0.7166	0.1751	0.057*
H14B	0.3910	0.8403	0.0992	0.057*
C15	0.0728 (2)	0.91872 (15)	0.58174 (12)	0.0335 (4)
C16	0.1614 (2)	0.95494 (15)	0.48134 (14)	0.0350 (4)
H16	0.271 (2)	0.9248 (16)	0.4737 (15)	0.037 (5)*
C17	0.09561 (19)	1.03470 (15)	0.39901 (12)	0.0327 (4)
C18	0.2204 (2)	1.06072 (16)	0.29829 (14)	0.0419 (4)
C19	0.1758 (2)	0.82880 (18)	0.65566 (15)	0.0459 (4)
N1	0.27157 (18)	0.75043 (15)	−0.04528 (11)	0.0452 (4)
H1A	0.2821	0.7007	−0.0999	0.054*
H1B	0.2974	0.8215	−0.0764	0.054*
N2	0.19315 (17)	0.79002 (15)	0.18387 (11)	0.0430 (4)
N3	0.26607 (16)	0.67052 (14)	0.33790 (11)	0.0396 (3)
N4	−0.01218 (15)	0.77067 (13)	0.33069 (10)	0.0338 (3)
N5	−0.21691 (15)	0.75273 (13)	0.48113 (11)	0.0333 (3)
O1	−0.37365 (18)	0.61061 (16)	0.80048 (11)	0.0640 (4)
OW1	0.34139 (19)	0.54945 (15)	0.80171 (12)	0.0614 (4)
HW1A	0.4401 (19)	0.557 (2)	0.7779 (18)	0.072*
HW1B	0.298 (2)	0.581 (2)	0.7463 (16)	0.070*
O2	−0.12330 (19)	0.52214 (15)	0.81832 (12)	0.0622 (4)
H2A	−0.018 (2)	0.516 (2)	0.7683 (19)	0.083 (8)*
OW2	0.3559 (2)	0.95983 (17)	0.85270 (14)	0.0721 (5)
HW2A	0.442 (3)	0.954 (3)	0.8054 (18)	0.097*
HW2B	0.353 (3)	1.013 (2)	0.8988 (19)	0.103*
O3	0.10748 (15)	0.53510 (12)	0.66146 (10)	0.0502 (3)
OW3	0.8262 (3)	0.59914 (18)	0.05037 (17)	0.0835 (5)
HW3A	0.764 (3)	0.562 (3)	0.0954 (17)	0.092*
HW3B	0.840 (4)	0.570 (3)	−0.0121 (15)	0.118*
OW4	0.6900 (2)	0.85376 (17)	0.01290 (14)	0.0782 (5)
HW4A	0.713 (4)	0.876 (2)	−0.0572 (15)	0.107*
HW4B	0.725 (3)	0.7783 (16)	0.022 (2)	0.092*
O4	0.17347 (18)	1.10598 (16)	0.20881 (11)	0.0655 (4)
O5	0.36177 (16)	1.03613 (14)	0.30721 (12)	0.0604 (4)
O6	0.1120 (2)	0.80744 (16)	0.75738 (11)	0.0660 (4)
H6A	0.002 (2)	0.842 (2)	0.772 (2)	0.084 (8)*
O7	0.31545 (18)	0.77853 (16)	0.61765 (13)	0.0728 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0499 (11)	0.0524 (11)	0.0330 (9)	−0.0199 (9)	−0.0005 (8)	−0.0002 (8)
C2	0.0399 (9)	0.0389 (9)	0.0298 (8)	−0.0142 (7)	−0.0017 (7)	−0.0034 (7)
C3	0.0377 (9)	0.0347 (8)	0.0327 (8)	−0.0095 (7)	−0.0074 (7)	−0.0035 (6)
C4	0.0312 (8)	0.0334 (8)	0.0311 (8)	−0.0097 (6)	−0.0052 (6)	−0.0039 (6)
C5	0.0305 (8)	0.0460 (10)	0.0352 (9)	−0.0059 (7)	−0.0080 (7)	−0.0036 (7)
C6	0.0310 (8)	0.0433 (9)	0.0284 (8)	−0.0123 (7)	−0.0040 (6)	−0.0072 (7)
C7	0.0283 (8)	0.0337 (8)	0.0280 (7)	−0.0097 (6)	−0.0042 (6)	−0.0068 (6)
C8	0.0308 (8)	0.0441 (10)	0.0324 (8)	−0.0124 (7)	0.0007 (6)	−0.0076 (7)
C9	0.0274 (8)	0.0474 (10)	0.0416 (9)	−0.0031 (7)	−0.0069 (7)	−0.0030 (7)
C10	0.0566 (13)	0.0637 (13)	0.0801 (15)	−0.0067 (10)	−0.0388 (12)	−0.0093 (11)
C11	0.0415 (10)	0.0579 (11)	0.0347 (9)	−0.0089 (8)	−0.0026 (7)	0.0040 (8)
C12	0.0452 (10)	0.0649 (12)	0.0352 (9)	−0.0233 (9)	−0.0109 (8)	0.0091 (8)
C13	0.0413 (10)	0.0584 (12)	0.0375 (10)	−0.0115 (9)	−0.0004 (8)	−0.0009 (8)
C14	0.0329 (9)	0.0750 (13)	0.0337 (9)	−0.0191 (9)	0.0004 (7)	−0.0023 (8)
C15	0.0365 (9)	0.0342 (8)	0.0304 (8)	−0.0091 (7)	−0.0076 (6)	−0.0026 (6)
C16	0.0298 (8)	0.0377 (9)	0.0365 (9)	−0.0083 (7)	−0.0045 (7)	−0.0047 (7)
C17	0.0368 (9)	0.0324 (8)	0.0288 (8)	−0.0115 (7)	−0.0022 (6)	−0.0045 (6)
C18	0.0458 (10)	0.0395 (9)	0.0358 (9)	−0.0133 (8)	0.0042 (7)	−0.0034 (7)
C19	0.0483 (11)	0.0515 (11)	0.0385 (10)	−0.0105 (9)	−0.0161 (8)	0.0025 (8)
N1	0.0549 (9)	0.0520 (9)	0.0302 (7)	−0.0205 (7)	−0.0041 (6)	−0.0018 (6)
N2	0.0332 (8)	0.0654 (10)	0.0276 (7)	−0.0139 (7)	−0.0012 (6)	0.0003 (7)
N3	0.0296 (7)	0.0550 (9)	0.0329 (7)	−0.0097 (6)	−0.0051 (6)	−0.0026 (6)
N4	0.0301 (7)	0.0423 (8)	0.0284 (7)	−0.0104 (6)	−0.0035 (5)	−0.0029 (6)
N5	0.0282 (7)	0.0410 (8)	0.0296 (7)	−0.0082 (6)	−0.0036 (5)	−0.0040 (5)
O1	0.0535 (9)	0.0927 (11)	0.0404 (7)	−0.0267 (8)	0.0077 (6)	0.0014 (7)
OW1	0.0568 (9)	0.0730 (10)	0.0537 (9)	−0.0144 (8)	−0.0185 (7)	0.0068 (7)
O2	0.0631 (10)	0.0786 (10)	0.0395 (7)	−0.0200 (8)	−0.0073 (7)	0.0145 (7)
OW2	0.0719 (11)	0.0748 (11)	0.0624 (10)	−0.0340 (9)	0.0177 (8)	−0.0015 (8)
O3	0.0469 (8)	0.0571 (8)	0.0416 (7)	−0.0086 (6)	−0.0123 (6)	0.0107 (6)
OW3	0.0943 (14)	0.0840 (13)	0.0773 (12)	−0.0392 (11)	−0.0119 (11)	0.0024 (10)
OW4	0.0926 (13)	0.0772 (11)	0.0517 (9)	−0.0234 (10)	0.0125 (9)	−0.0031 (9)
O4	0.0650 (10)	0.0936 (12)	0.0312 (7)	−0.0228 (8)	−0.0001 (6)	0.0087 (7)
O5	0.0412 (8)	0.0692 (9)	0.0569 (8)	−0.0126 (7)	0.0083 (6)	0.0090 (7)
O6	0.0667 (10)	0.0878 (11)	0.0363 (7)	−0.0113 (9)	−0.0163 (7)	0.0145 (7)
O7	0.0492 (9)	0.0929 (12)	0.0579 (9)	0.0087 (8)	−0.0165 (7)	0.0124 (8)

Geometric parameters (Å, º) top

C1—O1	1.219 (2)	C12—H12B	0.9700
C1—O2	1.320 (2)	C13—N1	1.489 (2)
C1—C2	1.475 (2)	C13—C14	1.503 (3)
C2—C8	1.368 (2)	C13—H13A	0.9700
C2—C3	1.430 (2)	C13—H13B	0.9700
C3—O3	1.268 (2)	C14—N2	1.462 (2)
C3—C4	1.439 (2)	C14—H14A	0.9700
C4—C7	1.400 (2)	C14—H14B	0.9700
C4—C5	1.401 (2)	C15—C16	1.393 (2)
C5—N3	1.311 (2)	C15—C17ⁱ	1.406 (2)
C5—H5A	0.9300	C15—C19	1.525 (2)
C6—N4	1.339 (2)	C16—C17	1.392 (2)
C6—N2	1.350 (2)	C16—H16	0.917 (19)
C6—N3	1.367 (2)	C17—C15ⁱ	1.406 (2)
C7—N4	1.3307 (19)	C17—C18	1.525 (2)
C7—N5	1.3834 (19)	C18—O5	1.230 (2)
C8—N5	1.345 (2)	C18—O4	1.275 (2)
C8—H8A	0.9300	C19—O7	1.213 (2)
C9—N5	1.487 (2)	C19—O6	1.285 (2)
C9—C10	1.499 (3)	N1—H1A	0.9000
C9—H9A	0.9700	N1—H1B	0.9000
C9—H9B	0.9700	OW1—HW1A	0.878 (15)
C10—H10A	0.9600	OW1—HW1B	0.854 (15)
C10—H10B	0.9600	O2—H2A	0.986 (16)
C10—H10C	0.9600	OW2—HW2A	0.842 (16)
C11—N2	1.451 (2)	OW2—HW2B	0.860 (16)
C11—C12	1.507 (3)	OW3—HW3A	0.849 (16)
C11—H11A	0.9700	OW3—HW3B	0.850 (17)
C11—H11B	0.9700	OW4—HW4A	0.871 (16)
C12—N1	1.491 (2)	OW4—HW4B	0.812 (16)
C12—H12A	0.9700	O6—H6A	0.924 (17)

O1—C1—O2	120.65 (17)	N1—C13—C14	110.52 (15)
O1—C1—C2	123.66 (18)	N1—C13—H13A	109.5
O2—C1—C2	115.69 (16)	C14—C13—H13A	109.5
C8—C2—C3	120.28 (14)	N1—C13—H13B	109.5
C8—C2—C1	119.08 (16)	C14—C13—H13B	109.5
C3—C2—C1	120.64 (15)	H13A—C13—H13B	108.1
O3—C3—C2	122.75 (15)	N2—C14—C13	109.98 (14)
O3—C3—C4	121.96 (15)	N2—C14—H14A	109.7
C2—C3—C4	115.29 (14)	C13—C14—H14A	109.7
C7—C4—C5	115.19 (14)	N2—C14—H14B	109.7
C7—C4—C3	121.64 (14)	C13—C14—H14B	109.7
C5—C4—C3	123.17 (15)	H14A—C14—H14B	108.2
N3—C5—C4	123.88 (15)	C16—C15—C17ⁱ	117.61 (15)
N3—C5—H5A	118.1	C16—C15—C19	113.70 (15)
C4—C5—H5A	118.1	C17ⁱ—C15—C19	128.68 (15)
N4—C6—N2	117.33 (15)	C17—C16—C15	124.81 (15)
N4—C6—N3	126.49 (14)	C17—C16—H16	120.7 (11)
N2—C6—N3	116.17 (14)	C15—C16—H16	114.4 (11)
N4—C7—N5	117.27 (13)	C16—C17—C15ⁱ	117.58 (14)
N4—C7—C4	123.16 (14)	C16—C17—C18	113.93 (15)
N5—C7—C4	119.57 (14)	C15ⁱ—C17—C18	128.49 (15)
N5—C8—C2	123.73 (15)	O5—C18—O4	123.21 (16)
N5—C8—H8A	118.1	O5—C18—C17	118.33 (16)
C2—C8—H8A	118.1	O4—C18—C17	118.46 (16)
N5—C9—C10	111.63 (15)	O7—C19—O6	121.26 (18)
N5—C9—H9A	109.3	O7—C19—C15	119.71 (17)
C10—C9—H9A	109.3	O6—C19—C15	119.03 (17)
N5—C9—H9B	109.3	C13—N1—C12	111.63 (13)
C10—C9—H9B	109.3	C13—N1—H1A	109.3
H9A—C9—H9B	108.0	C12—N1—H1A	109.3
C9—C10—H10A	109.5	C13—N1—H1B	109.3
C9—C10—H10B	109.5	C12—N1—H1B	109.3
H10A—C10—H10B	109.5	H1A—N1—H1B	108.0
C9—C10—H10C	109.5	C6—N2—C11	123.41 (14)
H10A—C10—H10C	109.5	C6—N2—C14	122.94 (15)
H10B—C10—H10C	109.5	C11—N2—C14	112.99 (13)
N2—C11—C12	110.08 (15)	C5—N3—C6	115.45 (14)
N2—C11—H11A	109.6	C7—N4—C6	115.83 (14)
C12—C11—H11A	109.6	C8—N5—C7	119.48 (14)
N2—C11—H11B	109.6	C8—N5—C9	120.08 (13)
C12—C11—H11B	109.6	C7—N5—C9	120.43 (13)
H11A—C11—H11B	108.2	HW1A—OW1—HW1B	101.7 (17)
N1—C12—C11	110.68 (14)	C1—O2—H2A	105.2 (15)
N1—C12—H12A	109.5	HW2A—OW2—HW2B	107 (2)
C11—C12—H12A	109.5	HW3A—OW3—HW3B	106 (2)
N1—C12—H12B	109.5	HW4A—OW4—HW4B	109 (2)
C11—C12—H12B	109.5	C19—O6—H6A	111.5 (16)
H12A—C12—H12B	108.1

Symmetry code: (i) −x, −y+2, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O6—H6A···O4ⁱ	0.92 (2)	1.47 (2)	2.392 (2)	178 (3)
N1—H1A···OW1ⁱⁱ	0.90	2.08	2.952 (2)	164
N1—H1A···O6ⁱⁱ	0.90	2.56	3.022 (2)	113
N1—H1B···OW2ⁱⁱ	0.90	1.82	2.717 (2)	176
OW1—HW1A···O1ⁱⁱⁱ	0.88 (2)	1.98 (2)	2.780 (2)	150 (2)
OW1—HW1B···O3	0.85 (2)	2.38 (2)	3.041 (2)	135 (2)
OW1—HW1B···O7	0.85 (2)	2.57 (2)	3.204 (2)	132 (2)
OW1—HW1B···O6	0.85 (2)	2.59 (2)	3.084 (2)	118 (2)
O2—H2A···O3	0.99 (2)	1.56 (2)	2.5013 (19)	159 (2)
OW2—HW2B···OW4^iv	0.86 (2)	1.86 (2)	2.703 (3)	168 (3)
OW2—HW2A···O5^iv	0.84 (2)	1.98 (2)	2.819 (2)	173 (3)
OW3—HW3A···OW1^v	0.85 (2)	1.93 (2)	2.770 (2)	169 (3)
OW3—HW3B···O2^vi	0.85 (2)	2.17 (2)	3.011 (3)	172 (3)
OW4—HW4A···O4^vii	0.87 (2)	1.94 (2)	2.782 (2)	163 (3)
OW4—HW4B···OW3	0.81 (2)	1.97 (2)	2.775 (3)	174 (3)

Symmetry codes: (i) −x, −y+2, −z+1; (ii) x, y, z−1; (iii) x+1, y, z; (iv) −x+1, −y+2, −z+1; (v) −x+1, −y+1, −z+1; (vi) x+1, y, z−1; (vii) −x+1, −y+2, −z.

Experimental details

Crystal data
Chemical formula	C₁₄H₁₈N₅O₃⁺·0.5C₁₀H₄O₈⁻·4H₂O
M_r	502.46
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	8.8336 (16), 11.103 (2), 12.445 (2)
α, β, γ (°)	83.010 (2), 76.737 (2), 73.831 (2)
V (Å³)	1138.9 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.12
Crystal size (mm)	0.52 × 0.48 × 0.39

Data collection
Diffractometer	Bruker APEX CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.940, 0.954
No. of measured, independent and observed [I > 2σ(I)] reflections	10252, 5071, 3550
R_int	0.021
(sin θ/λ)_max (Å⁻¹)	0.647

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.160, 1.01
No. of reflections	5071
No. of parameters	352
No. of restraints	14
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.33, −0.20

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL-Plus (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O6—H6A···O4ⁱ	0.924 (17)	1.468 (17)	2.392 (2)	178 (3)
N1—H1A···OW1ⁱⁱ	0.90	2.08	2.952 (2)	164
N1—H1A···O6ⁱⁱ	0.90	2.56	3.022 (2)	113
N1—H1B···OW2ⁱⁱ	0.90	1.82	2.717 (2)	176
OW1—HW1A···O1ⁱⁱⁱ	0.878 (15)	1.984 (17)	2.780 (2)	150 (2)
OW1—HW1B···O3	0.854 (15)	2.377 (18)	3.041 (2)	134.9 (19)
OW1—HW1B···O7	0.854 (15)	2.57 (2)	3.204 (2)	131.8 (18)
OW1—HW1B···O6	0.854 (15)	2.59 (2)	3.084 (2)	118 (2)
O2—H2A···O3	0.986 (16)	1.556 (18)	2.5013 (19)	159 (2)
OW2—HW2B···OW4^iv	0.860 (16)	1.856 (17)	2.703 (3)	168 (3)
OW2—HW2A···O5^iv	0.842 (16)	1.982 (17)	2.819 (2)	173 (3)
OW3—HW3A···OW1^v	0.849 (16)	1.931 (18)	2.770 (2)	169 (3)
OW3—HW3B···O2^vi	0.850 (17)	2.168 (17)	3.011 (3)	172 (3)
OW4—HW4A···O4^vii	0.871 (16)	1.937 (19)	2.782 (2)	163 (3)
OW4—HW4B···OW3	0.812 (16)	1.966 (17)	2.775 (3)	174 (3)

Symmetry codes: (i) −x, −y+2, −z+1; (ii) x, y, z−1; (iii) x+1, y, z; (iv) −x+1, −y+2, −z+1; (v) −x+1, −y+1, −z+1; (vi) x+1, y, z−1; (vii) −x+1, −y+2, −z.

Acknowledgements

This work was supported by the Science and Technology Foundation of Southwest University (SWUB2007035).

References

Bruker (2001). SMART and SAINT. Bruker AXS Inc., Madison Wisconsion, USA. Google Scholar
Mizuki, Y., Fujiwara, I. & Yamaguchi, T. (1996). J. Antimicrob. Chemother. Suppl. A, 37, 41–45. CrossRef CAS Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 67| Part 4| April 2011| Pages o1011-o1012

doi:10.1107/S1600536811011068

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

Bis[8-ethyl-5-oxo-2-(piperazin-4-ium-1-yl)-5,8-di­hydro­pyrido[2,3-d]pyrimidine-6-carb­­oxy­lic acid] 2,5-dicarb­­oxy­benzene-1,4-di­carboxyl­ate octa­hydrate

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

Bis[8-ethyl-5-oxo-2-(piperazin-4-ium-1-yl)-5,8-dihydropyrido[2,3-d]pyrimidine-6-carboxylic acid] 2,5-dicarboxybenzene-1,4-dicarboxylate octahydrate