4-(1-Cyclo­propyl-6-fluoro-4-oxo-1,4-dihydro­quinolin-7-yl)piperazin-1-ium 2,4,5-tricarb­oxy­benzene-1-carboxyl­ate monohydrate

Yan, S.-W.; Liang, Y.-C.; Liao, Q.; Xin, G.-H.; Ye, Z.-L.

doi:10.1107/S1600536812008392

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 68| Part 3| March 2012| Page o919

doi:10.1107/S1600536812008392

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4-(1-Cyclopropyl-6-fluoro-4-oxo-1,4-dihydroquinolin-7-yl)piperazin-1-ium 2,4,5-tricarboxybenzene-1-carboxylate monohydrate

Shi-Wei Yan,^a ^* Yan-Chen Liang,^a Qin Liao,^a Guang-Hua Xin ^a and Zhong-Li Ye ^a

^aCollege of Chemistry and Chemical Engineering, Southwest University, Chongqing 400715, People's Republic of China
^*Correspondence e-mail: yezi2010@swu.edu.cn

(Received 16 February 2012; accepted 24 February 2012; online 29 February 2012)

In the crystal of title compound, C₁₆H₁₉FN₃O⁺·C₁₀H₅O₈⁻·H₂O, the water molecule and the ions are connected by intermolecular N—H⋯O and O—H⋯O hydrogen bonds and π–π stacking [centroid–centroid separation = 3.602 (1) Å] between the benzene ring and the pyridine ring, generating a three-dimensional supramolecular structure.

Related literature

For general background on the use of quinolones in the treatment of infections, see: Barbas et al. (2006 ); Basavoju et al. (2006 ); Xiao et al. (2005 ).

Experimental

Crystal data

C₁₆H₁₉FN₃O⁺·C₁₀H₅O₈⁻·H₂O
M_r = 559.50
Triclinic, $[P \overline 1]$
a = 9.5537 (19) Å
b = 11.300 (2) Å
c = 11.686 (2) Å
α = 77.03 (3)°
β = 87.01 (3)°
γ = 88.65 (3)°
V = 1227.7 (4) Å³
Z = 2
Mo Kα radiation
μ = 0.12 mm⁻¹
T = 293 K
0.40 × 0.35 × 0.32 mm

Data collection

Bruker APEX CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.953, T_max = 0.962
12113 measured reflections
5561 independent reflections
3880 reflections with I > 2σ(I)
R_int = 0.024

Refinement

R[F² > 2σ(F²)] = 0.050
wR(F²) = 0.159
S = 0.99
5561 reflections
373 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.31 e Å⁻³
Δρ_min = −0.31 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1C⋯O3ⁱ	0.94	1.58	2.5170 (18)	177
O1—H1C⋯O4ⁱ	0.94	2.52	3.078 (2)	118
N1—H1B⋯O3ⁱ	0.93 (3)	2.54 (3)	3.006 (3)	111 (2)
N1—H1B⋯O1Wⁱⁱ	0.93 (3)	2.04 (3)	2.929 (3)	158 (2)
O8—H8A⋯O9ⁱⁱⁱ	1.00	1.52	2.519 (2)	178.2
Symmetry codes: (i) x+1, y, z; (ii) -x+2, -y, -z+2; (iii) -x+2, -y, -z+1.

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/S1600536812008392/ff2056sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812008392/ff2056Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812008392/ff2056Isup3.cml

checkCIF report

Comment top

Ciprofloxacin (cipH,1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-3-quinoline carboxylic acid) is member of a class of quinolones used to treat infections (Xiao et al. 2005; Barbas et al. 2006; Basavoju et al. 2006). In this paper, we synthesized the complex of L from cipH ligand, and then obtained the compound 1 by reaction with 1,2,4,5-H₄betc in hydrothermal conditions. Here we report the title compound 1.

As shown in Fig. 1, compound 1 contains one [HL]⁺ cation, one [1,2,4-H₃betc]^- anion and one H₂O molecule in the asymmetric unit. Then the molecules and the ions are further linked by intermolecular N—H···O and O—H···O hydrogen-bonding interactions (Table 1) and π–π stacking (separation 3.602 (1) Å) between the benzene rings and the pyridine rings to form a three-dimensional supramolecular structure.

Related literature top

For general background on the use of quinolones in the treatment of infections, see: Barbas et al. (2006); Basavoju et al. (2006); Xiao et al. (2005).

Experimental top

A mixture of Mn(CH₃COO)₂.4H₂O(0.123 g, 0.5 mmol), cipH (0.192 g, 0.5 mmol), 1,2,4,5-H₄betc (0.127, 0.5 mmol) and distilled water (7 ml) was stirred for 20 min in air. The mixture was then transferred to a 17 ml Teflon-lined hydrothermal bomb. The bomb was kept at 423 K for 129 h under autogenous pressure. Upon cooling, colorless block of 1 was obtained from the reaction mixture.

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, 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.

4-(1-Cyclopropyl-6-fluoro-4-oxo-1,4-dihydroquinolin-7-yl)piperazin-1-ium 2,4,5-tricarboxybenzene-1-carboxylate monohydrate top

Crystal data top

C₁₆H₁₉FN₃O⁺·C₁₀H₅O₈⁻·H₂O	Z = 2
M_r = 559.50	F(000) = 584
Triclinic, P1	D_x = 1.514 Mg m⁻³
a = 9.5537 (19) Å	Mo Kα radiation, λ = 0.71073 Å
b = 11.300 (2) Å	Cell parameters from 12113 reflections
c = 11.686 (2) Å	θ = 3.0–27.5°
α = 77.03 (3)°	µ = 0.12 mm⁻¹
β = 87.01 (3)°	T = 293 K
γ = 88.65 (3)°	Block, colourless
V = 1227.7 (4) Å³	0.40 × 0.35 × 0.32 mm

Data collection top

Bruker APEX CCD diffractometer	5561 independent reflections
Radiation source: fine-focus sealed tube	3880 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.024
ϕ and ω scans	θ_max = 27.5°, θ_min = 3.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→11
T_min = 0.953, T_max = 0.962	k = −13→14
12113 measured reflections	l = −15→15

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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.159	H atoms treated by a mixture of independent and constrained refinement
S = 0.99	w = 1/[σ²(F_o²) + (0.110P)²] where P = (F_o² + 2F_c²)/3
5561 reflections	(Δ/σ)_max < 0.001
373 parameters	Δρ_max = 0.31 e Å⁻³
1 restraint	Δρ_min = −0.31 e Å⁻³

Crystal data top

C₁₆H₁₉FN₃O⁺·C₁₀H₅O₈⁻·H₂O	γ = 88.65 (3)°
M_r = 559.50	V = 1227.7 (4) Å³
Triclinic, P1	Z = 2
a = 9.5537 (19) Å	Mo Kα radiation
b = 11.300 (2) Å	µ = 0.12 mm⁻¹
c = 11.686 (2) Å	T = 293 K
α = 77.03 (3)°	0.40 × 0.35 × 0.32 mm
β = 87.01 (3)°

Data collection top

Bruker APEX CCD diffractometer	5561 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3880 reflections with I > 2σ(I)
T_min = 0.953, T_max = 0.962	R_int = 0.024
12113 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.050	1 restraint
wR(F²) = 0.159	H atoms treated by a mixture of independent and constrained refinement
S = 0.99	Δρ_max = 0.31 e Å⁻³
5561 reflections	Δρ_min = −0.31 e Å⁻³
373 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	0.60114 (14)	0.33816 (15)	1.07824 (14)	0.0295 (3)
N1	1.01985 (19)	0.2831 (2)	0.83946 (17)	0.0547 (5)
H1A	0.957 (3)	0.321 (3)	0.878 (3)	0.079 (8)*
H1B	1.069 (3)	0.228 (3)	0.895 (3)	0.075 (8)*
O1	0.82943 (12)	0.29979 (18)	1.14009 (13)	0.0685 (5)
H1C	0.9252	0.3009	1.1161	0.082*
O1W	0.87507 (18)	−0.06407 (16)	1.0022 (2)	0.0926 (8)
H1WA	0.8177	−0.0216	0.9557	0.111*
H1WB	0.7853	−0.0240	1.0206	0.111*
F1	1.02031 (11)	0.14064 (13)	0.45876 (13)	0.0624 (4)
C2	0.54681 (15)	0.41608 (15)	1.14539 (14)	0.0299 (3)
H2A	0.6083	0.4647	1.1729	0.036*
N2	1.14351 (15)	0.24609 (15)	0.62194 (15)	0.0415 (4)
O2	0.80487 (12)	0.37949 (13)	0.95197 (12)	0.0477 (3)
C3	0.40408 (15)	0.42509 (14)	1.17374 (14)	0.0287 (3)
N3	1.59322 (15)	0.17920 (14)	0.42816 (13)	0.0380 (3)
O3	0.08715 (12)	0.3036 (2)	1.08262 (15)	0.0738 (6)
C4	0.31204 (14)	0.35278 (15)	1.12896 (14)	0.0292 (3)
O4	0.09600 (12)	0.37950 (14)	1.23777 (13)	0.0506 (4)
C5	0.36736 (15)	0.27751 (15)	1.05850 (15)	0.0309 (3)
H5A	0.3061	0.2322	1.0267	0.037*
O5	0.45510 (15)	0.59231 (14)	1.25440 (14)	0.0538 (4)
C6	0.51010 (14)	0.26699 (14)	1.03351 (14)	0.0289 (3)
O6	0.25111 (14)	0.50869 (15)	1.31073 (13)	0.0511 (4)
H6A	0.190 (3)	0.457 (3)	1.282 (3)	0.080 (9)*
C7	0.75666 (15)	0.33869 (15)	1.05065 (15)	0.0322 (4)
O7	0.68669 (13)	0.13815 (14)	0.97773 (15)	0.0549 (4)
C8	0.15442 (16)	0.34709 (17)	1.15168 (16)	0.0379 (4)
O8	0.47677 (13)	0.13899 (13)	0.90410 (13)	0.0462 (3)
H8A	0.5250	0.0896	0.8522	0.055*
C9	0.36945 (17)	0.51692 (16)	1.24860 (15)	0.0360 (4)
O9	1.40033 (17)	−0.01196 (15)	0.22317 (16)	0.0628 (4)
C10	0.56713 (16)	0.17555 (16)	0.96764 (16)	0.0349 (4)
C11	1.66801 (19)	0.12425 (18)	0.35279 (18)	0.0437 (4)
H11A	1.7651	0.1308	0.3486	0.052*
C12	1.6091 (2)	0.06014 (18)	0.28300 (19)	0.0472 (5)
H12A	1.6662	0.0252	0.2324	0.057*
C13	1.4631 (2)	0.04559 (17)	0.28592 (18)	0.0438 (4)
C14	1.38275 (19)	0.10197 (15)	0.36840 (16)	0.0376 (4)
C15	1.44897 (17)	0.16657 (15)	0.43999 (15)	0.0347 (4)
C16	1.36961 (17)	0.21379 (16)	0.52447 (15)	0.0357 (4)
H16A	1.4151	0.2539	0.5729	0.043*
C17	1.22544 (18)	0.20214 (16)	0.53736 (16)	0.0366 (4)
C18	1.16172 (19)	0.14494 (17)	0.45746 (18)	0.0421 (4)
C19	1.2362 (2)	0.09473 (17)	0.37802 (18)	0.0430 (4)
H19A	1.1897	0.0553	0.3296	0.052*
C20	1.21999 (19)	0.3099 (2)	0.6953 (2)	0.0491 (5)
H20A	1.2804	0.3702	0.6455	0.059*
H20B	1.2785	0.2524	0.7469	0.059*
C21	1.1188 (2)	0.3715 (2)	0.7680 (2)	0.0586 (6)
H21A	1.1708	0.4092	0.8192	0.070*
H21B	1.0670	0.4348	0.7164	0.070*
C22	0.9432 (2)	0.2206 (2)	0.7649 (2)	0.0552 (5)
H22A	0.8870	0.2789	0.7119	0.066*
H22B	0.8808	0.1613	0.8136	0.066*
C23	1.0456 (2)	0.1578 (2)	0.6948 (2)	0.0546 (5)
H23A	1.0979	0.0963	0.7479	0.065*
H23B	0.9948	0.1179	0.6447	0.065*
C24	1.66395 (19)	0.25073 (19)	0.49675 (17)	0.0438 (4)
H24A	1.6722	0.2135	0.5804	0.053*
C25	1.7802 (2)	0.3311 (2)	0.4393 (2)	0.0533 (5)
H25A	1.8061	0.3323	0.3577	0.064*
H25B	1.8575	0.3412	0.4868	0.064*
C26	1.6408 (2)	0.3841 (2)	0.46637 (19)	0.0499 (5)
H26A	1.6338	0.4263	0.5302	0.060*
H26B	1.5824	0.4174	0.4011	0.060*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0195 (7)	0.0390 (9)	0.0314 (8)	0.0013 (6)	0.0018 (6)	−0.0117 (7)
N1	0.0458 (9)	0.0744 (13)	0.0467 (10)	0.0155 (9)	0.0116 (8)	−0.0240 (9)
O1	0.0156 (6)	0.1473 (17)	0.0407 (8)	0.0011 (7)	−0.0006 (5)	−0.0176 (9)
O1W	0.0558 (10)	0.0569 (10)	0.167 (2)	0.0104 (8)	−0.0303 (12)	−0.0242 (12)
F1	0.0350 (6)	0.0850 (10)	0.0770 (9)	0.0021 (5)	0.0012 (6)	−0.0402 (8)
C2	0.0227 (7)	0.0405 (9)	0.0295 (8)	−0.0016 (6)	−0.0016 (6)	−0.0144 (7)
N2	0.0365 (7)	0.0475 (9)	0.0444 (9)	−0.0012 (6)	0.0147 (6)	−0.0220 (7)
O2	0.0322 (6)	0.0623 (9)	0.0429 (8)	0.0087 (5)	0.0136 (5)	−0.0043 (6)
C3	0.0246 (7)	0.0355 (8)	0.0275 (8)	0.0041 (6)	−0.0008 (6)	−0.0108 (6)
N3	0.0354 (7)	0.0431 (8)	0.0340 (8)	0.0071 (6)	0.0057 (6)	−0.0081 (6)
O3	0.0160 (6)	0.1546 (18)	0.0704 (11)	−0.0076 (7)	0.0026 (6)	−0.0669 (12)
C4	0.0176 (6)	0.0395 (9)	0.0316 (8)	0.0033 (5)	−0.0006 (6)	−0.0105 (6)
O4	0.0260 (6)	0.0772 (10)	0.0547 (9)	−0.0001 (6)	0.0115 (6)	−0.0310 (7)
C5	0.0216 (7)	0.0376 (9)	0.0372 (9)	−0.0014 (6)	−0.0012 (6)	−0.0159 (7)
O5	0.0540 (8)	0.0583 (9)	0.0593 (9)	−0.0052 (6)	0.0054 (7)	−0.0361 (7)
C6	0.0212 (7)	0.0349 (8)	0.0334 (8)	0.0022 (5)	−0.0002 (6)	−0.0144 (7)
O6	0.0396 (7)	0.0739 (10)	0.0494 (9)	0.0046 (6)	0.0076 (6)	−0.0366 (7)
C7	0.0210 (7)	0.0424 (9)	0.0364 (9)	−0.0012 (6)	0.0038 (6)	−0.0167 (7)
O7	0.0311 (6)	0.0642 (9)	0.0816 (11)	0.0138 (6)	−0.0027 (7)	−0.0437 (8)
C8	0.0195 (7)	0.0567 (11)	0.0392 (9)	0.0029 (6)	0.0013 (7)	−0.0151 (8)
O8	0.0384 (7)	0.0542 (8)	0.0573 (9)	0.0032 (5)	−0.0023 (6)	−0.0364 (7)
C9	0.0340 (8)	0.0448 (10)	0.0327 (9)	0.0076 (7)	−0.0015 (7)	−0.0171 (7)
O9	0.0694 (10)	0.0643 (10)	0.0674 (11)	−0.0015 (7)	0.0143 (8)	−0.0453 (8)
C10	0.0273 (8)	0.0390 (9)	0.0419 (10)	0.0000 (6)	0.0039 (7)	−0.0175 (7)
C11	0.0379 (9)	0.0470 (11)	0.0423 (10)	0.0107 (7)	0.0119 (8)	−0.0061 (8)
C12	0.0565 (11)	0.0414 (10)	0.0427 (10)	0.0112 (8)	0.0163 (9)	−0.0131 (8)
C13	0.0570 (11)	0.0350 (9)	0.0401 (10)	0.0060 (8)	0.0099 (8)	−0.0135 (8)
C14	0.0454 (9)	0.0326 (9)	0.0358 (9)	0.0054 (7)	0.0068 (7)	−0.0123 (7)
C15	0.0381 (8)	0.0332 (9)	0.0308 (8)	0.0058 (6)	0.0064 (7)	−0.0054 (7)
C16	0.0368 (9)	0.0403 (9)	0.0310 (9)	0.0037 (7)	0.0058 (7)	−0.0123 (7)
C17	0.0393 (9)	0.0344 (9)	0.0367 (9)	0.0040 (6)	0.0086 (7)	−0.0120 (7)
C18	0.0361 (9)	0.0446 (10)	0.0479 (11)	0.0033 (7)	0.0034 (8)	−0.0168 (8)
C19	0.0466 (10)	0.0422 (10)	0.0449 (11)	0.0000 (7)	0.0021 (8)	−0.0208 (8)
C20	0.0393 (9)	0.0599 (12)	0.0554 (12)	−0.0029 (8)	0.0130 (8)	−0.0313 (10)
C21	0.0584 (12)	0.0630 (14)	0.0634 (14)	0.0004 (10)	0.0168 (10)	−0.0375 (11)
C22	0.0406 (10)	0.0732 (15)	0.0520 (12)	0.0010 (9)	0.0169 (9)	−0.0193 (11)
C23	0.0468 (10)	0.0613 (13)	0.0588 (13)	−0.0067 (9)	0.0204 (9)	−0.0248 (11)
C24	0.0357 (9)	0.0642 (12)	0.0312 (9)	0.0042 (8)	−0.0013 (7)	−0.0106 (8)
C25	0.0429 (10)	0.0704 (14)	0.0481 (12)	−0.0046 (9)	0.0033 (9)	−0.0170 (10)
C26	0.0488 (10)	0.0632 (13)	0.0442 (11)	0.0030 (9)	−0.0028 (9)	−0.0261 (10)

Geometric parameters (Å, º) top

C1—C2	1.381 (2)	O8—C10	1.299 (2)
C1—C6	1.395 (2)	O8—H8A	1.0011
C1—C7	1.504 (2)	O9—C13	1.264 (2)
N1—C22	1.471 (3)	C11—C12	1.356 (3)
N1—C21	1.476 (3)	C11—H11A	0.9300
N1—H1A	0.89 (3)	C12—C13	1.406 (3)
N1—H1B	0.93 (3)	C12—H12A	0.9300
O1—C7	1.274 (2)	C13—C14	1.449 (3)
O1—H1C	0.9423	C14—C19	1.402 (3)
O1W—H1WA	0.8534	C14—C15	1.409 (3)
O1W—H1WB	0.9965	C15—C16	1.405 (2)
F1—C18	1.352 (2)	C16—C17	1.384 (2)
C2—C3	1.393 (2)	C16—H16A	0.9300
C2—H2A	0.9300	C17—C18	1.417 (3)
N2—C17	1.399 (2)	C18—C19	1.356 (3)
N2—C20	1.468 (3)	C19—H19A	0.9300
N2—C23	1.475 (3)	C20—C21	1.513 (3)
O2—C7	1.213 (2)	C20—H20A	0.9700
C3—C4	1.410 (2)	C20—H20B	0.9700
C3—C9	1.521 (2)	C21—H21A	0.9700
N3—C11	1.353 (2)	C21—H21B	0.9700
N3—C15	1.385 (2)	C22—C23	1.508 (3)
N3—C24	1.458 (2)	C22—H22A	0.9700
O3—C8	1.246 (2)	C22—H22B	0.9700
C4—C5	1.389 (2)	C23—H23A	0.9700
C4—C8	1.516 (2)	C23—H23B	0.9700
O4—C8	1.247 (2)	C24—C26	1.483 (3)
C5—C6	1.388 (2)	C24—C25	1.485 (3)
C5—H5A	0.9300	C24—H24A	0.9800
O5—C9	1.210 (2)	C25—C26	1.495 (3)
C6—C10	1.498 (2)	C25—H25A	0.9700
O6—C9	1.305 (2)	C25—H25B	0.9700
O6—H6A	0.96 (3)	C26—H26A	0.9700
O7—C10	1.211 (2)	C26—H26B	0.9700

C2—C1—C6	119.26 (13)	N3—C15—C16	120.88 (16)
C2—C1—C7	118.20 (14)	N3—C15—C14	119.00 (16)
C6—C1—C7	122.45 (14)	C16—C15—C14	120.09 (16)
C22—N1—C21	110.98 (18)	C17—C16—C15	121.64 (17)
C22—N1—H1A	108.0 (18)	C17—C16—H16A	119.2
C21—N1—H1A	110.1 (19)	C15—C16—H16A	119.2
C22—N1—H1B	111.1 (18)	C16—C17—N2	123.13 (17)
C21—N1—H1B	109.4 (18)	C16—C17—C18	116.46 (16)
H1A—N1—H1B	107 (3)	N2—C17—C18	120.39 (16)
C7—O1—H1C	109.4	F1—C18—C19	117.83 (17)
H1WA—O1W—H1WB	50.5	F1—C18—C17	119.17 (16)
C1—C2—C3	122.95 (14)	C19—C18—C17	122.99 (17)
C1—C2—H2A	118.5	C18—C19—C14	120.40 (18)
C3—C2—H2A	118.5	C18—C19—H19A	119.8
C17—N2—C20	115.57 (14)	C14—C19—H19A	119.8
C17—N2—C23	115.15 (15)	N2—C20—C21	110.56 (16)
C20—N2—C23	110.83 (17)	N2—C20—H20A	109.5
C2—C3—C4	117.79 (14)	C21—C20—H20A	109.5
C2—C3—C9	113.40 (14)	N2—C20—H20B	109.5
C4—C3—C9	128.79 (13)	C21—C20—H20B	109.5
C11—N3—C15	119.49 (16)	H20A—C20—H20B	108.1
C11—N3—C24	120.26 (15)	N1—C21—C20	110.75 (19)
C15—N3—C24	120.26 (15)	N1—C21—H21A	109.5
C5—C4—C3	118.78 (13)	C20—C21—H21A	109.5
C5—C4—C8	115.23 (14)	N1—C21—H21B	109.5
C3—C4—C8	125.98 (15)	C20—C21—H21B	109.5
C6—C5—C4	122.83 (14)	H21A—C21—H21B	108.1
C6—C5—H5A	118.6	N1—C22—C23	109.77 (17)
C4—C5—H5A	118.6	N1—C22—H22A	109.7
C5—C6—C1	118.33 (14)	C23—C22—H22A	109.7
C5—C6—C10	121.34 (13)	N1—C22—H22B	109.7
C1—C6—C10	120.18 (13)	C23—C22—H22B	109.7
C9—O6—H6A	108.6 (19)	H22A—C22—H22B	108.2
O2—C7—O1	124.70 (14)	N2—C23—C22	110.56 (18)
O2—C7—C1	121.15 (15)	N2—C23—H23A	109.5
O1—C7—C1	114.03 (15)	C22—C23—H23A	109.5
O3—C8—O4	121.84 (15)	N2—C23—H23B	109.5
O3—C8—C4	116.41 (16)	C22—C23—H23B	109.5
O4—C8—C4	121.68 (15)	H23A—C23—H23B	108.1
C10—O8—H8A	110.2	N3—C24—C26	117.23 (15)
O5—C9—O6	121.09 (17)	N3—C24—C25	118.92 (17)
O5—C9—C3	119.46 (16)	C26—C24—C25	60.50 (15)
O6—C9—C3	119.33 (16)	N3—C24—H24A	116.2
O7—C10—O8	124.51 (17)	C26—C24—H24A	116.2
O7—C10—C6	121.15 (15)	C25—C24—H24A	116.2
O8—C10—C6	114.30 (13)	C24—C25—C26	59.67 (14)
N3—C11—C12	123.56 (17)	C24—C25—H25A	117.8
N3—C11—H11A	118.2	C26—C25—H25A	117.8
C12—C11—H11A	118.2	C24—C25—H25B	117.8
C11—C12—C13	121.11 (18)	C26—C25—H25B	117.8
C11—C12—H12A	119.4	H25A—C25—H25B	114.9
C13—C12—H12A	119.4	C24—C26—C25	59.83 (14)
O9—C13—C12	124.86 (18)	C24—C26—H26A	117.8
O9—C13—C14	119.59 (18)	C25—C26—H26A	117.8
C12—C13—C14	115.55 (18)	C24—C26—H26B	117.8
C19—C14—C15	118.14 (16)	C25—C26—H26B	117.8
C19—C14—C13	120.63 (17)	H26A—C26—H26B	114.9
C15—C14—C13	121.23 (17)

C6—C1—C2—C3	1.8 (3)	C12—C13—C14—C15	0.0 (3)
C7—C1—C2—C3	178.42 (14)	C11—N3—C15—C16	174.60 (16)
C1—C2—C3—C4	−1.5 (2)	C24—N3—C15—C16	−5.1 (2)
C1—C2—C3—C9	179.95 (15)	C11—N3—C15—C14	−3.4 (2)
C2—C3—C4—C5	−0.6 (2)	C24—N3—C15—C14	176.89 (15)
C9—C3—C4—C5	177.76 (16)	C19—C14—C15—N3	−177.24 (16)
C2—C3—C4—C8	178.52 (15)	C13—C14—C15—N3	2.0 (2)
C9—C3—C4—C8	−3.2 (3)	C19—C14—C15—C16	4.8 (3)
C3—C4—C5—C6	2.4 (3)	C13—C14—C15—C16	−175.96 (16)
C8—C4—C5—C6	−176.81 (15)	N3—C15—C16—C17	179.91 (16)
C4—C5—C6—C1	−2.1 (3)	C14—C15—C16—C17	−2.1 (3)
C4—C5—C6—C10	173.58 (16)	C15—C16—C17—N2	178.80 (16)
C2—C1—C6—C5	0.0 (2)	C15—C16—C17—C18	−2.7 (3)
C7—C1—C6—C5	−176.49 (15)	C20—N2—C17—C16	1.9 (3)
C2—C1—C6—C10	−175.70 (15)	C23—N2—C17—C16	−129.4 (2)
C7—C1—C6—C10	7.8 (3)	C20—N2—C17—C18	−176.54 (18)
C2—C1—C7—O2	−109.5 (2)	C23—N2—C17—C18	52.2 (2)
C6—C1—C7—O2	67.1 (2)	C16—C17—C18—F1	−174.11 (17)
C2—C1—C7—O1	66.7 (2)	N2—C17—C18—F1	4.4 (3)
C6—C1—C7—O1	−116.7 (2)	C16—C17—C18—C19	5.2 (3)
C5—C4—C8—O3	−18.7 (3)	N2—C17—C18—C19	−176.27 (18)
C3—C4—C8—O3	162.20 (19)	F1—C18—C19—C14	176.68 (17)
C5—C4—C8—O4	158.39 (17)	C17—C18—C19—C14	−2.6 (3)
C3—C4—C8—O4	−20.7 (3)	C15—C14—C19—C18	−2.4 (3)
C2—C3—C9—O5	17.1 (2)	C13—C14—C19—C18	178.29 (18)
C4—C3—C9—O5	−161.24 (18)	C17—N2—C20—C21	170.19 (18)
C2—C3—C9—O6	−158.98 (15)	C23—N2—C20—C21	−56.5 (2)
C4—C3—C9—O6	22.6 (3)	C22—N1—C21—C20	−56.8 (3)
C5—C6—C10—O7	−155.79 (18)	N2—C20—C21—N1	55.8 (3)
C1—C6—C10—O7	19.8 (3)	C21—N1—C22—C23	57.8 (3)
C5—C6—C10—O8	22.1 (2)	C17—N2—C23—C22	−168.47 (18)
C1—C6—C10—O8	−162.35 (16)	C20—N2—C23—C22	58.0 (2)
C15—N3—C11—C12	2.8 (3)	N1—C22—C23—N2	−58.2 (3)
C24—N3—C11—C12	−177.46 (18)	C11—N3—C24—C26	110.6 (2)
N3—C11—C12—C13	−0.7 (3)	C15—N3—C24—C26	−69.7 (2)
C11—C12—C13—O9	179.5 (2)	C11—N3—C24—C25	41.0 (3)
C11—C12—C13—C14	−0.7 (3)	C15—N3—C24—C25	−139.30 (18)
O9—C13—C14—C19	−0.9 (3)	N3—C24—C25—C26	106.74 (19)
C12—C13—C14—C19	179.23 (18)	N3—C24—C26—C25	−109.50 (19)
O9—C13—C14—C15	179.84 (18)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1C···O3ⁱ	0.94	1.58	2.5170 (18)	177
O1—H1C···O4ⁱ	0.94	2.52	3.078 (2)	118
N1—H1B···O3ⁱ	0.93 (3)	2.54 (3)	3.006 (3)	111 (2)
N1—H1B···O1Wⁱⁱ	0.93 (3)	2.04 (3)	2.929 (3)	158 (2)
O8—H8A···O9ⁱⁱⁱ	1.00	1.52	2.519 (2)	178.2

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

Experimental details

Crystal data
Chemical formula	C₁₆H₁₉FN₃O⁺·C₁₀H₅O₈⁻·H₂O
M_r	559.50
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	9.5537 (19), 11.300 (2), 11.686 (2)
α, β, γ (°)	77.03 (3), 87.01 (3), 88.65 (3)
V (Å³)	1227.7 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.12
Crystal size (mm)	0.40 × 0.35 × 0.32

Data collection
Diffractometer	Bruker APEX CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.953, 0.962
No. of measured, independent and observed [I > 2σ(I)] reflections	12113, 5561, 3880
R_int	0.024
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.050, 0.159, 0.99
No. of reflections	5561
No. of parameters	373
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.31, −0.31

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
O1—H1C···O3ⁱ	0.94	1.58	2.5170 (18)	177.0
O1—H1C···O4ⁱ	0.94	2.52	3.078 (2)	118.1
N1—H1B···O3ⁱ	0.93 (3)	2.54 (3)	3.006 (3)	111 (2)
N1—H1B···O1Wⁱⁱ	0.93 (3)	2.04 (3)	2.929 (3)	158 (2)
O8—H8A···O9ⁱⁱⁱ	1.00	1.52	2.519 (2)	178.2

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

Acknowledgements

This work was financially supported by the Science and Technology Foundation of Southwest University (grant No. SWUB2007035) and the Science and Technology Innovation Foundation for Students of Southwest University.

References

Barbas, R., Martí, F., Prohens, R. & Puigjaner, C. (2006). Cryst. Growth Des. 6, 1463–1467. Web of Science CrossRef CAS Google Scholar
Basavoju, S., Boström, D. & Velaga, S. P. (2006). Cryst. Growth Des. 6, 2699–2708. Web of Science CSD CrossRef CAS Google Scholar
Bruker (2001). SMART and SAINT Bruker AXS Inc., Madison, Wisconsin, USA. 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
Xiao, D.-R., Wang, E.-B., An, H.-Y., Su, Z.-M., Li, Y.-G., Gao, L., Sun, C.-Y. & Xu, L. (2005). Chem. Eur. J. 11, 6673–6686. Web of Science CSD CrossRef PubMed CAS Google Scholar

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Volume 68| Part 3| March 2012| Page o919

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

4-(1-Cyclo­propyl-6-fluoro-4-oxo-1,4-di­hydro­quinolin-7-yl)piperazin-1-ium 2,4,5-tricarb­­oxy­benzene-1-carboxyl­ate monohydrate

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

4-(1-Cyclopropyl-6-fluoro-4-oxo-1,4-dihydroquinolin-7-yl)piperazin-1-ium 2,4,5-tricarboxybenzene-1-carboxylate monohydrate