4-(3-Carb­oxy-1-ethyl-6-fluoro-4-oxo-1,4-dihydroquinolin-7-yl)piperazin-1-ium 4-carb­oxy­benzoate–benzene-1,4-dicarb­oxy­lic acid (2/1)

Yan, S.-W.; Chen, H.-Y.; Zhang, G.-J.; Liao, Q.; Liang, Y.-C.

doi:10.1107/S1600536811009524

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 67| Part 4| April 2011| Page o909

doi:10.1107/S1600536811009524

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4-(3-Carboxy-1-ethyl-6-fluoro-4-oxo-1,4-dihydroquinolin-7-yl)piperazin-1-ium 4-carboxybenzoate–benzene-1,4-dicarboxylic acid (2/1)

Shi-Wei Yan,^a ^* Hai-Yan Chen,^a Guang-Ju Zhang,^a Qin Liao ^a and Yan-Chen Liang ^a

^aCollege of Chemistry and Chemical Engineering, Southwest University, Chongqing 400715, People's Republic of China
^*Correspondence e-mail: yanshiwei158@163.com

(Received 2 March 2011; accepted 13 March 2011; online 19 March 2011)

In the title compound, C₁₆H₁₉FN₃O₃⁺·C₈H₅O₄⁻·0.5C₈H₆O₄, the benzene-1,4-dicarboxylic acid molecule is located on a centre of symmetry. In the crystal, the molecules and ions are connected by intermolecular C—H⋯O and O—H⋯O hydrogen bonds and π–π stacking interactions [with a centroid–centroid distance of 3.402 (2) Å], generating a three-dimensional supramolecular structure.

Related literature

For general background to 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

C₁₆H₁₉FN₃O₃⁺·C₈H₅O₄⁻·0.5C₈H₆O₄
M_r = 568.53
Triclinic, $[P \overline 1]$
a = 9.8901 (15) Å
b = 10.2420 (16) Å
c = 13.665 (2) Å
α = 89.304 (2)°
β = 74.672 (2)°
γ = 71.677 (2)°
V = 1263.5 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.12 mm⁻¹
T = 296 K
0.46 × 0.45 × 0.36 mm

Data collection

Bruker APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.948, T_max = 0.959
10704 measured reflections
5143 independent reflections
4031 reflections with I > 2σ(I)
R_int = 0.024

Refinement

R[F² > 2σ(F²)] = 0.042
wR(F²) = 0.137
S = 1.00
5143 reflections
394 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.26 e Å⁻³
Δρ_min = −0.28 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C15—H15B⋯O1ⁱ	0.97	2.38	3.274 (2)	153
O5—H5B⋯O7ⁱⁱ	0.97 (3)	1.70 (3)	2.6648 (15)	169 (2)
Symmetry codes: (i) -x+1, -y, -z+1; (ii) x-1, y, 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/S1600536811009524/ff2003sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811009524/ff2003Isup2.hkl

checkCIF report

Comment top

Norfloxacin [1–Ethyl–6–fluoro–1,4–dihydro–4–oxo–7–(piperazin–1–yl)quinoline–3–carbo–xylic 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,the structure of the title compound, 1, is described (Fig. 1). In compound 1, benzene-1,4-dicarboxylic acid is located on the centre of symmetry. The molecules and the ions are linked by intermolecular C—H···O and O—H···O hydrogen-bonding interactions (C···O = 3.273 (2) Å, O···O = 2.6648 (18) Å) and π—π stacking between the benzene ring of [H₂norf]⁺ and aromatic ring of 1,4-H₂bdc with the centroid-centroid distance of 3.402 (2) Å, generating a three-dimensional supramolecular structure.

Related literature top

For general background to 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 (0.061 g, 0.25 mmol), Norfloxacin (0.080 g, 0.25 mmol) and distilled water (10 ml) was stirred for 20 min. in air. The mixture was then transferred to a 23 ml Teflon-lined hydrothermal bomb. The bomb was kept at 393 K for 96 h under autogenous pressure. Upon cooling, yellow block 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 havebeen omitted for clarity [Symmetry code: -x+2, -y, -z+1].

4-(3-Carboxy-1-ethyl-6-fluoro-4-oxo-1,4-dihydroquinolin-7-yl)piperazin-1-ium 4-carboxybenzoate–benzene-1,4-dicarboxylic acid (2/1) top

Crystal data top

C₁₆H₁₉FN₃O₃⁺·C₈H₅O₄⁻·0.5C₈H₆O₄	Z = 2
M_r = 568.53	F(000) = 594
Triclinic, P1	D_x = 1.494 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.8901 (15) Å	Cell parameters from 10704 reflections
b = 10.2420 (16) Å	θ = 2.5–26.4°
c = 13.665 (2) Å	µ = 0.12 mm⁻¹
α = 89.304 (2)°	T = 296 K
β = 74.672 (2)°	Block, yellow
γ = 71.677 (2)°	0.46 × 0.45 × 0.36 mm
V = 1263.5 (3) Å³

Data collection top

Bruker APEX CCD area-detector diffractometer	5143 independent reflections
Radiation source: fine-focus sealed tube	4031 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.024
ϕ and ω scans	θ_max = 26.4°, θ_min = 2.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→12
T_min = 0.948, T_max = 0.959	k = −12→12
10704 measured reflections	l = −17→17

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.137	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ²(F_o²) + (0.095P)²] where P = (F_o² + 2F_c²)/3
5143 reflections	(Δ/σ)_max < 0.001
394 parameters	Δρ_max = 0.26 e Å⁻³
0 restraints	Δρ_min = −0.28 e Å⁻³

Crystal data top

C₁₆H₁₉FN₃O₃⁺·C₈H₅O₄⁻·0.5C₈H₆O₄	γ = 71.677 (2)°
M_r = 568.53	V = 1263.5 (3) Å³
Triclinic, P1	Z = 2
a = 9.8901 (15) Å	Mo Kα radiation
b = 10.2420 (16) Å	µ = 0.12 mm⁻¹
c = 13.665 (2) Å	T = 296 K
α = 89.304 (2)°	0.46 × 0.45 × 0.36 mm
β = 74.672 (2)°

Data collection top

Bruker APEX CCD area-detector diffractometer	5143 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	4031 reflections with I > 2σ(I)
T_min = 0.948, T_max = 0.959	R_int = 0.024
10704 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	0 restraints
wR(F²) = 0.137	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	Δρ_max = 0.26 e Å⁻³
5143 reflections	Δρ_min = −0.28 e Å⁻³
394 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
F1	0.63577 (11)	0.18180 (9)	0.27698 (7)	0.0431 (3)
C1	0.63370 (16)	−0.02848 (19)	0.79008 (11)	0.0389 (4)
C2	0.65495 (15)	−0.05532 (16)	0.68003 (10)	0.0307 (3)
C3	0.63043 (15)	0.05539 (15)	0.61573 (11)	0.0290 (3)
C4	0.66237 (14)	0.01485 (14)	0.50870 (10)	0.0258 (3)
C5	0.64110 (15)	0.11621 (15)	0.43912 (10)	0.0275 (3)
H5A	0.6076	0.2090	0.4619	0.033*
C6	0.66906 (15)	0.07966 (14)	0.33949 (10)	0.0276 (3)
C7	0.72669 (15)	−0.05884 (15)	0.29813 (10)	0.0264 (3)
C8	0.75114 (15)	−0.15922 (15)	0.36672 (10)	0.0277 (3)
H8A	0.7915	−0.2517	0.3427	0.033*
C9	0.71625 (14)	−0.12410 (14)	0.47136 (10)	0.0258 (3)
C10	0.70628 (16)	−0.18915 (16)	0.63933 (11)	0.0320 (3)
H10A	0.7198	−0.2588	0.6836	0.038*
C11	0.79437 (18)	−0.37552 (16)	0.50584 (12)	0.0397 (4)
H11A	0.8377	−0.4277	0.5560	0.048*
H11B	0.8717	−0.3910	0.4423	0.048*
C12	0.6737 (2)	−0.42777 (18)	0.49078 (15)	0.0524 (5)
H12A	0.7149	−0.5242	0.4686	0.079*
H12B	0.6316	−0.3776	0.4403	0.079*
H12C	0.5979	−0.4147	0.5539	0.079*
C13	0.82815 (18)	−0.02111 (17)	0.11838 (11)	0.0367 (4)
H13A	0.9339	−0.0663	0.1060	0.044*
H13B	0.8050	0.0741	0.1427	0.044*
C14	0.78474 (18)	−0.02599 (16)	0.02080 (11)	0.0377 (4)
H14A	0.6795	0.0219	0.0328	0.045*
H14B	0.8381	0.0201	−0.0302	0.045*
C15	0.74848 (17)	−0.24840 (16)	0.06232 (11)	0.0353 (4)
H15A	0.7813	−0.3450	0.0383	0.042*
H15B	0.6419	−0.2125	0.0739	0.042*
C16	0.78617 (19)	−0.23578 (15)	0.16120 (11)	0.0363 (4)
H16A	0.7325	−0.2810	0.2127	0.044*
H16B	0.8913	−0.2813	0.1517	0.044*
C17	0.17400 (16)	0.50636 (16)	0.20944 (11)	0.0330 (3)
C18	0.33786 (15)	0.48186 (14)	0.18335 (11)	0.0290 (3)
C19	0.43591 (16)	0.39424 (16)	0.10056 (12)	0.0350 (3)
H19A	0.4000	0.3534	0.0571	0.042*
C20	0.58733 (16)	0.36724 (16)	0.08232 (11)	0.0344 (3)
H20A	0.6523	0.3088	0.0264	0.041*
C21	0.64275 (15)	0.42664 (14)	0.14690 (11)	0.0281 (3)
C22	0.54455 (16)	0.51661 (16)	0.22799 (12)	0.0348 (3)
H22A	0.5804	0.5588	0.2707	0.042*
C23	0.39284 (16)	0.54453 (16)	0.24616 (12)	0.0356 (4)
H23A	0.3278	0.6056	0.3007	0.043*
C24	0.80895 (16)	0.38823 (15)	0.12883 (12)	0.0321 (3)
C25	0.97781 (16)	0.15488 (18)	0.32394 (12)	0.0371 (4)
C26	0.98985 (15)	0.07643 (17)	0.41574 (11)	0.0330 (3)
C27	1.04199 (16)	−0.06690 (17)	0.40371 (12)	0.0354 (4)
H27A	1.0697	−0.1117	0.3392	0.042*
C28	1.05276 (16)	−0.14308 (18)	0.48721 (12)	0.0356 (4)
H28	1.087 (2)	−0.246 (2)	0.4790 (14)	0.054 (5)*
N1	0.74725 (14)	−0.09079 (12)	0.19528 (9)	0.0306 (3)
N2	0.81977 (15)	−0.17166 (14)	−0.01670 (9)	0.0327 (3)
H2A	0.923 (2)	−0.2219 (19)	−0.0393 (13)	0.049 (5)*
H2B	0.785 (2)	−0.169 (2)	−0.0715 (15)	0.055 (5)*
N3	0.73831 (13)	−0.22629 (12)	0.54007 (9)	0.0305 (3)
O1	0.60295 (14)	0.10171 (15)	0.82150 (9)	0.0489 (3)
H1A	0.595 (3)	0.154 (3)	0.760 (2)	0.104 (9)*
O2	0.64619 (14)	−0.11994 (15)	0.84810 (9)	0.0522 (3)
O3	0.58611 (12)	0.18033 (11)	0.64870 (8)	0.0391 (3)
O4	0.08777 (13)	0.57308 (16)	0.28487 (10)	0.0622 (4)
O5	0.13363 (12)	0.44329 (13)	0.14372 (9)	0.0466 (3)
H5B	0.030 (3)	0.448 (2)	0.1690 (17)	0.087 (7)*
O6	0.88873 (12)	0.30848 (14)	0.05353 (9)	0.0533 (3)
O7	0.85565 (11)	0.43952 (11)	0.19277 (9)	0.0379 (3)
O8	1.01763 (14)	0.10184 (13)	0.23849 (9)	0.0520 (3)
O9	0.91792 (16)	0.28979 (13)	0.34610 (10)	0.0565 (4)
H9A	0.903 (3)	0.334 (2)	0.2932 (18)	0.080 (8)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
F1	0.0595 (6)	0.0329 (5)	0.0350 (5)	−0.0096 (4)	−0.0165 (4)	0.0123 (4)
C1	0.0302 (8)	0.0629 (11)	0.0270 (8)	−0.0185 (8)	−0.0093 (6)	0.0033 (8)
C2	0.0241 (7)	0.0454 (9)	0.0242 (7)	−0.0122 (6)	−0.0079 (6)	0.0031 (6)
C3	0.0215 (6)	0.0374 (8)	0.0271 (7)	−0.0080 (6)	−0.0069 (5)	−0.0025 (6)
C4	0.0208 (6)	0.0323 (8)	0.0245 (7)	−0.0080 (6)	−0.0069 (5)	0.0007 (6)
C5	0.0259 (7)	0.0254 (7)	0.0295 (7)	−0.0062 (6)	−0.0071 (6)	−0.0001 (6)
C6	0.0281 (7)	0.0284 (7)	0.0284 (7)	−0.0092 (6)	−0.0113 (6)	0.0079 (6)
C7	0.0265 (7)	0.0333 (8)	0.0221 (7)	−0.0127 (6)	−0.0075 (5)	0.0013 (6)
C8	0.0280 (7)	0.0262 (7)	0.0266 (7)	−0.0058 (6)	−0.0072 (6)	−0.0001 (5)
C9	0.0218 (6)	0.0307 (7)	0.0246 (7)	−0.0077 (6)	−0.0073 (5)	0.0043 (6)
C10	0.0291 (7)	0.0420 (9)	0.0265 (7)	−0.0106 (6)	−0.0114 (6)	0.0087 (6)
C11	0.0431 (9)	0.0297 (8)	0.0338 (8)	0.0027 (7)	−0.0076 (7)	0.0049 (6)
C12	0.0648 (12)	0.0311 (9)	0.0544 (11)	−0.0102 (8)	−0.0109 (9)	−0.0027 (8)
C13	0.0433 (9)	0.0441 (9)	0.0285 (8)	−0.0239 (7)	−0.0079 (6)	0.0049 (6)
C14	0.0460 (9)	0.0390 (9)	0.0270 (8)	−0.0145 (7)	−0.0073 (7)	0.0066 (6)
C15	0.0378 (8)	0.0392 (9)	0.0290 (8)	−0.0145 (7)	−0.0066 (6)	−0.0042 (6)
C16	0.0504 (9)	0.0330 (8)	0.0267 (8)	−0.0152 (7)	−0.0103 (7)	0.0006 (6)
C17	0.0268 (7)	0.0366 (8)	0.0350 (8)	−0.0092 (6)	−0.0087 (6)	0.0019 (6)
C18	0.0255 (7)	0.0310 (7)	0.0320 (8)	−0.0101 (6)	−0.0090 (6)	0.0048 (6)
C19	0.0310 (8)	0.0404 (9)	0.0365 (8)	−0.0125 (7)	−0.0126 (6)	−0.0041 (7)
C20	0.0291 (8)	0.0369 (8)	0.0339 (8)	−0.0078 (6)	−0.0066 (6)	−0.0035 (6)
C21	0.0251 (7)	0.0276 (7)	0.0341 (8)	−0.0099 (6)	−0.0106 (6)	0.0080 (6)
C22	0.0305 (8)	0.0378 (8)	0.0388 (8)	−0.0130 (6)	−0.0116 (6)	−0.0044 (7)
C23	0.0295 (8)	0.0366 (8)	0.0371 (8)	−0.0086 (6)	−0.0053 (6)	−0.0072 (6)
C24	0.0253 (7)	0.0329 (8)	0.0392 (8)	−0.0097 (6)	−0.0108 (6)	0.0093 (6)
C25	0.0283 (7)	0.0475 (10)	0.0373 (9)	−0.0137 (7)	−0.0104 (6)	0.0057 (7)
C26	0.0224 (7)	0.0436 (9)	0.0349 (8)	−0.0123 (6)	−0.0091 (6)	0.0047 (6)
C27	0.0264 (7)	0.0459 (9)	0.0331 (8)	−0.0107 (7)	−0.0079 (6)	−0.0004 (7)
C28	0.0272 (7)	0.0412 (9)	0.0389 (9)	−0.0113 (7)	−0.0093 (6)	0.0020 (7)
N1	0.0415 (7)	0.0314 (7)	0.0225 (6)	−0.0164 (5)	−0.0090 (5)	0.0023 (5)
N2	0.0295 (7)	0.0435 (8)	0.0228 (6)	−0.0085 (6)	−0.0070 (5)	−0.0016 (5)
N3	0.0306 (6)	0.0311 (7)	0.0263 (6)	−0.0045 (5)	−0.0089 (5)	0.0046 (5)
O1	0.0497 (7)	0.0647 (8)	0.0289 (6)	−0.0152 (6)	−0.0086 (5)	−0.0086 (6)
O2	0.0622 (8)	0.0773 (9)	0.0300 (6)	−0.0324 (7)	−0.0226 (6)	0.0168 (6)
O3	0.0424 (6)	0.0386 (6)	0.0321 (6)	−0.0085 (5)	−0.0082 (5)	−0.0078 (5)
O4	0.0288 (6)	0.0954 (11)	0.0531 (8)	−0.0150 (6)	−0.0005 (6)	−0.0288 (7)
O5	0.0263 (6)	0.0604 (8)	0.0531 (7)	−0.0146 (5)	−0.0095 (5)	−0.0155 (6)
O6	0.0265 (6)	0.0708 (9)	0.0519 (8)	−0.0039 (6)	−0.0068 (5)	−0.0122 (6)
O7	0.0282 (5)	0.0403 (6)	0.0514 (7)	−0.0136 (5)	−0.0183 (5)	0.0077 (5)
O8	0.0606 (8)	0.0560 (8)	0.0367 (7)	−0.0143 (6)	−0.0146 (6)	0.0056 (6)
O9	0.0783 (10)	0.0429 (8)	0.0424 (8)	−0.0081 (7)	−0.0208 (7)	0.0090 (6)

Geometric parameters (Å, º) top

F1—C6	1.3576 (16)	C15—H15A	0.9700
C1—O2	1.217 (2)	C15—H15B	0.9700
C1—O1	1.321 (2)	C16—N1	1.4604 (18)
C1—C2	1.479 (2)	C16—H16A	0.9700
C2—C10	1.370 (2)	C16—H16B	0.9700
C2—C3	1.426 (2)	C17—O4	1.2012 (18)
C3—O3	1.2607 (18)	C17—O5	1.3225 (18)
C3—C4	1.4490 (19)	C17—C18	1.5025 (19)
C4—C9	1.402 (2)	C18—C19	1.387 (2)
C4—C5	1.404 (2)	C18—C23	1.387 (2)
C5—C6	1.349 (2)	C19—C20	1.388 (2)
C5—H5A	0.9300	C19—H19A	0.9300
C6—C7	1.413 (2)	C20—C21	1.389 (2)
C7—C8	1.391 (2)	C20—H20A	0.9300
C7—N1	1.3936 (17)	C21—C22	1.383 (2)
C8—C9	1.4023 (19)	C21—C24	1.5162 (19)
C8—H8A	0.9300	C22—C23	1.389 (2)
C9—N3	1.4020 (18)	C22—H22A	0.9300
C10—N3	1.3397 (18)	C23—H23A	0.9300
C10—H10A	0.9300	C24—O6	1.2388 (18)
C11—N3	1.4865 (19)	C24—O7	1.2766 (18)
C11—C12	1.513 (3)	C25—O8	1.2048 (19)
C11—H11A	0.9700	C25—O9	1.324 (2)
C11—H11B	0.9700	C25—C26	1.493 (2)
C12—H12A	0.9600	C26—C27	1.390 (2)
C12—H12B	0.9600	C26—C28ⁱ	1.396 (2)
C12—H12C	0.9600	C27—C28	1.383 (2)
C13—N1	1.4663 (18)	C27—H27A	0.9300
C13—C14	1.511 (2)	C28—C26ⁱ	1.396 (2)
C13—H13A	0.9700	C28—H28	1.00 (2)
C13—H13B	0.9700	N2—H2A	0.95 (2)
C14—N2	1.486 (2)	N2—H2B	0.90 (2)
C14—H14A	0.9700	O1—H1A	1.01 (3)
C14—H14B	0.9700	O5—H5B	0.97 (3)
C15—N2	1.4854 (19)	O9—H9A	0.87 (2)
C15—C16	1.511 (2)

O2—C1—O1	121.77 (15)	H15A—C15—H15B	108.0
O2—C1—C2	122.66 (16)	N1—C16—C15	110.42 (12)
O1—C1—C2	115.55 (15)	N1—C16—H16A	109.6
C10—C2—C3	120.06 (13)	C15—C16—H16A	109.6
C10—C2—C1	118.91 (14)	N1—C16—H16B	109.6
C3—C2—C1	120.95 (14)	C15—C16—H16B	109.6
O3—C3—C2	122.78 (13)	H16A—C16—H16B	108.1
O3—C3—C4	121.79 (13)	O4—C17—O5	122.82 (14)
C2—C3—C4	115.42 (13)	O4—C17—C18	123.26 (14)
C9—C4—C5	118.25 (12)	O5—C17—C18	113.87 (13)
C9—C4—C3	121.91 (13)	C19—C18—C23	119.20 (13)
C5—C4—C3	119.84 (13)	C19—C18—C17	121.79 (13)
C6—C5—C4	120.33 (13)	C23—C18—C17	118.96 (13)
C6—C5—H5A	119.8	C18—C19—C20	120.29 (13)
C4—C5—H5A	119.8	C18—C19—H19A	119.9
C5—C6—F1	117.76 (12)	C20—C19—H19A	119.9
C5—C6—C7	123.34 (13)	C19—C20—C21	120.57 (14)
F1—C6—C7	118.88 (12)	C19—C20—H20A	119.7
C8—C7—N1	122.74 (13)	C21—C20—H20A	119.7
C8—C7—C6	116.28 (12)	C22—C21—C20	119.00 (12)
N1—C7—C6	120.84 (12)	C22—C21—C24	121.62 (13)
C7—C8—C9	121.46 (13)	C20—C21—C24	119.35 (13)
C7—C8—H8A	119.3	C21—C22—C23	120.57 (13)
C9—C8—H8A	119.3	C21—C22—H22A	119.7
N3—C9—C4	118.79 (12)	C23—C22—H22A	119.7
N3—C9—C8	120.97 (12)	C18—C23—C22	120.33 (14)
C4—C9—C8	120.22 (13)	C18—C23—H23A	119.8
N3—C10—C2	124.37 (14)	C22—C23—H23A	119.8
N3—C10—H10A	117.8	O6—C24—O7	125.16 (13)
C2—C10—H10A	117.8	O6—C24—C21	117.30 (13)
N3—C11—C12	112.40 (13)	O7—C24—C21	117.54 (13)
N3—C11—H11A	109.1	O8—C25—O9	123.17 (15)
C12—C11—H11A	109.1	O8—C25—C26	123.95 (15)
N3—C11—H11B	109.1	O9—C25—C26	112.88 (14)
C12—C11—H11B	109.1	C27—C26—C28ⁱ	119.59 (15)
H11A—C11—H11B	107.9	C27—C26—C25	118.64 (14)
C11—C12—H12A	109.5	C28ⁱ—C26—C25	121.76 (15)
C11—C12—H12B	109.5	C28—C27—C26	120.27 (15)
H12A—C12—H12B	109.5	C28—C27—H27A	119.9
C11—C12—H12C	109.5	C26—C27—H27A	119.9
H12A—C12—H12C	109.5	C27—C28—C26ⁱ	120.14 (15)
H12B—C12—H12C	109.5	C27—C28—H28	120.3 (11)
N1—C13—C14	109.50 (12)	C26ⁱ—C28—H28	119.5 (11)
N1—C13—H13A	109.8	C7—N1—C16	117.61 (12)
C14—C13—H13A	109.8	C7—N1—C13	119.55 (11)
N1—C13—H13B	109.8	C16—N1—C13	110.22 (11)
C14—C13—H13B	109.8	C15—N2—C14	111.24 (11)
H13A—C13—H13B	108.2	C15—N2—H2A	108.2 (11)
N2—C14—C13	109.94 (13)	C14—N2—H2A	114.5 (11)
N2—C14—H14A	109.7	C15—N2—H2B	109.8 (13)
C13—C14—H14A	109.7	C14—N2—H2B	106.8 (12)
N2—C14—H14B	109.7	H2A—N2—H2B	106.1 (15)
C13—C14—H14B	109.7	C10—N3—C9	119.45 (12)
H14A—C14—H14B	108.2	C10—N3—C11	118.90 (12)
N2—C15—C16	111.36 (12)	C9—N3—C11	121.65 (11)
N2—C15—H15A	109.4	C1—O1—H1A	105.0 (15)
C16—C15—H15A	109.4	C17—O5—H5B	111.4 (13)
N2—C15—H15B	109.4	C25—O9—H9A	112.3 (15)
C16—C15—H15B	109.4

O2—C1—C2—C10	−7.3 (2)	C18—C19—C20—C21	0.4 (2)
O1—C1—C2—C10	171.42 (13)	C19—C20—C21—C22	−2.0 (2)
O2—C1—C2—C3	176.10 (13)	C19—C20—C21—C24	176.19 (13)
O1—C1—C2—C3	−5.2 (2)	C20—C21—C22—C23	1.6 (2)
C10—C2—C3—O3	−178.58 (13)	C24—C21—C22—C23	−176.53 (14)
C1—C2—C3—O3	−2.0 (2)	C19—C18—C23—C22	−1.9 (2)
C10—C2—C3—C4	0.41 (19)	C17—C18—C23—C22	175.66 (14)
C1—C2—C3—C4	176.99 (12)	C21—C22—C23—C18	0.3 (2)
O3—C3—C4—C9	177.89 (12)	C22—C21—C24—O6	−178.99 (14)
C2—C3—C4—C9	−1.10 (19)	C20—C21—C24—O6	2.9 (2)
O3—C3—C4—C5	−1.3 (2)	C22—C21—C24—O7	1.6 (2)
C2—C3—C4—C5	179.68 (12)	C20—C21—C24—O7	−176.52 (13)
C9—C4—C5—C6	1.4 (2)	O8—C25—C26—C27	−3.9 (2)
C3—C4—C5—C6	−179.33 (12)	O9—C25—C26—C27	175.87 (13)
C4—C5—C6—F1	175.05 (11)	O8—C25—C26—C28ⁱ	177.53 (15)
C4—C5—C6—C7	−3.0 (2)	O9—C25—C26—C28ⁱ	−2.7 (2)
C5—C6—C7—C8	1.4 (2)	C28ⁱ—C26—C27—C28	−0.5 (2)
F1—C6—C7—C8	−176.64 (12)	C25—C26—C27—C28	−179.12 (13)
C5—C6—C7—N1	177.13 (13)	C26—C27—C28—C26ⁱ	0.5 (2)
F1—C6—C7—N1	−0.92 (19)	C8—C7—N1—C16	4.3 (2)
N1—C7—C8—C9	−173.88 (12)	C6—C7—N1—C16	−171.11 (13)
C6—C7—C8—C9	1.8 (2)	C8—C7—N1—C13	−133.83 (14)
C5—C4—C9—N3	179.84 (12)	C6—C7—N1—C13	50.73 (19)
C3—C4—C9—N3	0.61 (19)	C15—C16—N1—C7	158.69 (12)
C5—C4—C9—C8	1.64 (19)	C15—C16—N1—C13	−59.52 (16)
C3—C4—C9—C8	−177.59 (12)	C14—C13—N1—C7	−157.19 (13)
C7—C8—C9—N3	178.57 (12)	C14—C13—N1—C16	61.86 (16)
C7—C8—C9—C4	−3.3 (2)	C16—C15—N2—C14	−53.27 (17)
C3—C2—C10—N3	0.8 (2)	C13—C14—N2—C15	55.27 (16)
C1—C2—C10—N3	−175.81 (13)	C2—C10—N3—C9	−1.4 (2)
N1—C13—C14—N2	−59.34 (17)	C2—C10—N3—C11	179.53 (13)
N2—C15—C16—N1	55.06 (16)	C4—C9—N3—C10	0.64 (19)
O4—C17—C18—C19	174.08 (16)	C8—C9—N3—C10	178.82 (12)
O5—C17—C18—C19	−3.4 (2)	C4—C9—N3—C11	179.68 (12)
O4—C17—C18—C23	−3.4 (2)	C8—C9—N3—C11	−2.1 (2)
O5—C17—C18—C23	179.09 (14)	C12—C11—N3—C10	98.46 (16)
C23—C18—C19—C20	1.5 (2)	C12—C11—N3—C9	−80.58 (17)
C17—C18—C19—C20	−175.97 (14)

Symmetry code: (i) −x+2, −y, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15B···O1ⁱⁱ	0.97	2.38	3.274 (2)	153
O5—H5B···O7ⁱⁱⁱ	0.97 (3)	1.70 (3)	2.6648 (15)	169 (2)

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

Experimental details

Crystal data
Chemical formula	C₁₆H₁₉FN₃O₃⁺·C₈H₅O₄⁻·0.5C₈H₆O₄
M_r	568.53
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	9.8901 (15), 10.2420 (16), 13.665 (2)
α, β, γ (°)	89.304 (2), 74.672 (2), 71.677 (2)
V (Å³)	1263.5 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.12
Crystal size (mm)	0.46 × 0.45 × 0.36

Data collection
Diffractometer	Bruker APEX CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.948, 0.959
No. of measured, independent and observed [I > 2σ(I)] reflections	10704, 5143, 4031
R_int	0.024
(sin θ/λ)_max (Å⁻¹)	0.626

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.137, 1.00
No. of reflections	5143
No. of parameters	394
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.26, −0.28

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
C15—H15B···O1ⁱ	0.97	2.38	3.274 (2)	153
O5—H5B···O7ⁱⁱ	0.97 (3)	1.70 (3)	2.6648 (15)	169 (2)

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

Acknowledgements

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

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). SADABS 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 67| Part 4| April 2011| Page o909

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

4-(3-Carb­­oxy-1-ethyl-6-fluoro-4-oxo-1,4-di­hydroquinolin-7-yl)piperazin-1-ium 4-carb­­oxy­benzoate–benzene-1,4-dicarb­­oxy­lic acid (2/1)

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

4-(3-Carboxy-1-ethyl-6-fluoro-4-oxo-1,4-dihydroquinolin-7-yl)piperazin-1-ium 4-carboxybenzoate–benzene-1,4-dicarboxylic acid (2/1)