Norfloxacin sesquihydrate.

IN THE CRYSTAL STRUCTURE OF THE TITLE COMPOUND [SYSTEMATIC NAME: 1-ethyl-6-fluoro-4-oxo-7-(piperazin-4-ium-1-yl)-1,4-dihydro-quinoline-3-carboxyl-ate sesquihydrate], C(16)H(18)FN(3)O(3)·1.42H(2)O, N-H⋯O and O-H⋯O hydrogen bonds assemble the mol-ecules in a two-dimensional layered corrugated sheet structure parallel to the b axis. The water mol-ecules are disordered [occupancies 0.741 (11) and 0.259 (11)].

Related literature

For related structures, see: Yuasa et al. (1982 ▶); Windholz et al. (1983 ▶); Katdare et al. (1986 ▶); Šuštar et al. (1993 ▶); Florence et al. (2000 ▶); Barbas et al. (2006 ▶); Basavoju et al. (2006 ▶); Barbas et al. (2007 ▶); Chongcharoen et al. (2008 ▶)

Experimental

Crystal data

C16H18FN3O3·1.42H2O

M = 344.12

Monoclinic,

a = 8.8434 (18) Å

b = 22.312 (5) Å

c = 8.7564 (18) Å

β = 109.35 (3)°

V = 1630.2 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 298 (2) K

0.20 × 0.20 × 0.10 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: none

16819 measured reflections

3228 independent reflections

2553 reflections with I > 2σ(I)

R int = 0.044

Refinement

R[F 2 > 2σ(F 2)] = 0.081

wR(F 2) = 0.218

S = 1.03

3228 reflections

253 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.37 e Å−3

Δρmin = −0.26 e Å−3

Data collection: SMART (Bruker, 1997 ▶); cell refinement: SAINT (Bruker, 1997 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053680900066X/gw2057sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680900066X/gw2057Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C16H18FN3O3·1.42H2O	F(000) = 725.5
Mr = 344.12	Dx = 1.402 Mg m−3
Monoclinic, P21/c	Melting point: 492.5(3) K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 8.8434 (18) Å	Cell parameters from 3228 reflections
b = 22.312 (5) Å	θ = 1.8–26.1°
c = 8.7564 (18) Å	µ = 0.11 mm−1
β = 109.35 (3)°	T = 298 K
V = 1630.2 (7) Å3	Block, pale yellow
Z = 4	0.20 × 0.20 × 0.10 mm

Bruker SMART CCD area-detector diffractometer	2553 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.044
graphite	θmax = 26.1°, θmin = 1.8°
φ and ω scans	h = −10→10
16819 measured reflections	k = −27→27
3228 independent reflections	l = −10→10

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)] = 0.081	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.218	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.1124P)2 + 1.8021P] where P = (Fo2 + 2Fc2)/3
3228 reflections	(Δ/σ)max < 0.001
253 parameters	Δρmax = 0.37 e Å−3
0 restraints	Δρmin = −0.26 e Å−3

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.

	x	y	z	Uiso*/Ueq	Occ. (<1)
F1	0.2851 (2)	0.73405 (8)	0.1027 (2)	0.0442 (5)
C9	0.5896 (4)	0.69034 (13)	0.4775 (4)	0.0313 (7)
H9	0.6340	0.6563	0.5365	0.038*
N1	0.7787 (3)	0.75248 (11)	0.6815 (3)	0.0313 (6)
C8	0.4641 (3)	0.68388 (13)	0.3326 (4)	0.0302 (7)
C10	0.6513 (4)	0.74655 (12)	0.5373 (4)	0.0282 (6)
N2	0.4098 (3)	0.62818 (11)	0.2644 (3)	0.0338 (6)
C6	0.4554 (4)	0.79261 (13)	0.3075 (4)	0.0304 (7)
H6	0.4079	0.8265	0.2498	0.037*
C7	0.4011 (4)	0.73759 (13)	0.2506 (4)	0.0312 (7)
C4	0.6462 (4)	0.85899 (13)	0.5062 (4)	0.0313 (7)
C1	0.8307 (4)	0.80766 (13)	0.7354 (4)	0.0327 (7)
H1	0.9128	0.8101	0.8344	0.039*
C2	0.7747 (4)	0.86019 (13)	0.6590 (4)	0.0315 (7)
O1	0.9214 (3)	0.91437 (11)	0.8908 (3)	0.0543 (7)
O3	0.5884 (3)	0.90336 (10)	0.4227 (3)	0.0509 (7)
O2	0.8443 (3)	0.96306 (11)	0.6594 (3)	0.0563 (8)
C5	0.5828 (3)	0.79879 (12)	0.4528 (3)	0.0278 (6)
C3	0.8524 (4)	0.91709 (13)	0.7418 (4)	0.0330 (7)
C14	0.4966 (4)	0.57470 (13)	0.3422 (4)	0.0378 (8)
H14A	0.4622	0.5633	0.4325	0.045*
H14B	0.6105	0.5832	0.3838	0.045*
N3	0.2914 (3)	0.51183 (11)	0.1476 (3)	0.0382 (7)
H3A	0.2528	0.4972	0.2232	0.046*
H3B	0.2762	0.4840	0.0697	0.046*
C15	0.8690 (4)	0.70072 (14)	0.7748 (4)	0.0391 (8)
H15A	0.9077	0.7109	0.8890	0.047*
H15B	0.7972	0.6667	0.7607	0.047*
C12	0.2026 (4)	0.56722 (14)	0.0767 (4)	0.0427 (8)
H12A	0.0884	0.5589	0.0367	0.051*
H12B	0.2344	0.5803	−0.0138	0.051*
C11	0.2368 (4)	0.61614 (14)	0.2023 (4)	0.0381 (8)
H11A	0.1796	0.6523	0.1545	0.046*
H11B	0.2002	0.6039	0.2904	0.046*
C13	0.4652 (4)	0.52396 (14)	0.2223 (4)	0.0393 (8)
H13A	0.5099	0.5339	0.1381	0.047*
H13B	0.5186	0.4881	0.2767	0.047*
C16	1.0069 (5)	0.6835 (2)	0.7236 (5)	0.0635 (12)
H16A	0.9684	0.6701	0.6132	0.095*
H16B	1.0656	0.6517	0.7916	0.095*
H16C	1.0758	0.7175	0.7327	0.095*
O4A	0.1091 (6)	0.4638 (2)	0.3166 (6)	0.0616 (18)	0.741 (11)
O5	0.2349 (14)	0.5705 (7)	0.6166 (16)	0.076 (3)	0.423 (6)
O4B	0.1742 (14)	0.4991 (6)	0.4249 (17)	0.059 (5)	0.259 (11)
H4B	0.134 (8)	0.463 (3)	0.440 (8)	0.13 (2)*
H4A	0.020 (11)	0.489 (4)	0.282 (10)	0.19 (4)*

	U11	U22	U33	U12	U13	U23
F1	0.0476 (11)	0.0359 (10)	0.0394 (11)	−0.0060 (8)	0.0016 (9)	−0.0039 (8)
C9	0.0353 (16)	0.0209 (14)	0.0396 (17)	0.0036 (12)	0.0149 (13)	0.0037 (12)
N1	0.0330 (14)	0.0235 (12)	0.0355 (14)	0.0007 (10)	0.0086 (11)	0.0014 (10)
C8	0.0312 (15)	0.0244 (15)	0.0392 (17)	−0.0002 (12)	0.0170 (13)	−0.0039 (12)
C10	0.0320 (15)	0.0221 (14)	0.0342 (16)	−0.0016 (11)	0.0160 (13)	−0.0018 (12)
N2	0.0301 (14)	0.0221 (13)	0.0485 (16)	−0.0002 (10)	0.0118 (12)	−0.0066 (11)
C6	0.0339 (16)	0.0232 (14)	0.0351 (16)	0.0020 (12)	0.0128 (13)	0.0033 (12)
C7	0.0298 (15)	0.0320 (16)	0.0313 (16)	−0.0018 (12)	0.0094 (12)	−0.0039 (12)
C4	0.0355 (16)	0.0229 (14)	0.0350 (16)	−0.0020 (12)	0.0112 (13)	−0.0017 (12)
C1	0.0321 (16)	0.0328 (16)	0.0314 (16)	0.0006 (13)	0.0082 (12)	−0.0010 (13)
C2	0.0330 (16)	0.0275 (15)	0.0348 (16)	−0.0018 (12)	0.0123 (13)	−0.0026 (12)
O1	0.0660 (17)	0.0436 (15)	0.0409 (14)	−0.0094 (12)	0.0010 (12)	−0.0095 (11)
O3	0.0640 (17)	0.0217 (11)	0.0489 (15)	−0.0043 (11)	−0.0056 (12)	0.0063 (10)
O2	0.0724 (18)	0.0306 (13)	0.0495 (15)	−0.0186 (12)	−0.0017 (13)	0.0018 (11)
C5	0.0313 (15)	0.0228 (14)	0.0314 (15)	−0.0014 (11)	0.0134 (12)	−0.0009 (11)
C3	0.0289 (15)	0.0274 (16)	0.0406 (18)	0.0006 (12)	0.0086 (13)	−0.0054 (13)
C14	0.0335 (16)	0.0258 (15)	0.051 (2)	0.0005 (13)	0.0106 (14)	−0.0029 (14)
N3	0.0458 (16)	0.0211 (13)	0.0436 (16)	−0.0045 (11)	0.0093 (13)	−0.0048 (11)
C15	0.0448 (19)	0.0286 (17)	0.0395 (18)	0.0020 (14)	0.0080 (14)	0.0079 (13)
C12	0.0379 (18)	0.0264 (16)	0.054 (2)	−0.0032 (13)	0.0015 (15)	−0.0004 (14)
C11	0.0303 (17)	0.0266 (16)	0.056 (2)	−0.0009 (12)	0.0121 (14)	−0.0022 (14)
C13	0.0409 (18)	0.0226 (15)	0.054 (2)	0.0026 (13)	0.0153 (15)	−0.0055 (14)
C16	0.060 (3)	0.063 (3)	0.072 (3)	0.025 (2)	0.029 (2)	0.021 (2)
O4A	0.061 (3)	0.058 (3)	0.071 (3)	0.020 (2)	0.031 (2)	0.024 (3)
O5	0.048 (6)	0.101 (10)	0.066 (8)	0.015 (6)	0.003 (5)	−0.015 (7)
O4B	0.052 (7)	0.060 (9)	0.071 (10)	0.007 (6)	0.030 (6)	0.038 (8)

F1—C7	1.361 (3)	C14—C13	1.506 (4)
C9—C8	1.389 (4)	C14—H14A	0.9700
C9—C10	1.398 (4)	C14—H14B	0.9700
C9—H9	0.9300	N3—C13	1.483 (4)
N1—C1	1.344 (4)	N3—C12	1.485 (4)
N1—C10	1.392 (4)	N3—H3A	0.9000
N1—C15	1.486 (4)	N3—H3B	0.9000
C8—N2	1.393 (4)	C15—C16	1.483 (5)
C8—C7	1.413 (4)	C15—H15A	0.9700
C10—C5	1.406 (4)	C15—H15B	0.9700
N2—C14	1.459 (4)	C12—C11	1.507 (5)
N2—C11	1.469 (4)	C12—H12A	0.9700
C6—C7	1.352 (4)	C12—H12B	0.9700
C6—C5	1.399 (4)	C11—H11A	0.9700
C6—H6	0.9300	C11—H11B	0.9700
C4—O3	1.236 (4)	C13—H13A	0.9700
C4—C2	1.441 (4)	C13—H13B	0.9700
C4—C5	1.471 (4)	C16—H16A	0.9600
C1—C2	1.359 (4)	C16—H16B	0.9600
C1—H1	0.9300	C16—H16C	0.9600
C2—C3	1.510 (4)	O4A—H4B	1.03 (7)
O1—C3	1.245 (4)	O4A—H4A	0.93 (10)
O2—C3	1.242 (4)	O4B—H4B	0.91 (7)
C8—C9—C10	122.0 (3)	C13—C14—H14B	109.7
C8—C9—H9	119.0	H14A—C14—H14B	108.2
C10—C9—H9	119.0	C13—N3—C12	111.1 (2)
C1—N1—C10	119.0 (2)	C13—N3—H3A	109.4
C1—N1—C15	117.4 (3)	C12—N3—H3A	109.4
C10—N1—C15	123.4 (2)	C13—N3—H3B	109.4
C9—C8—N2	122.8 (3)	C12—N3—H3B	109.4
C9—C8—C7	115.9 (3)	H3A—N3—H3B	108.0
N2—C8—C7	121.1 (3)	C16—C15—N1	112.4 (3)
N1—C10—C9	121.6 (3)	C16—C15—H15A	109.1
N1—C10—C5	118.5 (2)	N1—C15—H15A	109.1
C9—C10—C5	120.0 (3)	C16—C15—H15B	109.1
C8—N2—C14	118.4 (3)	N1—C15—H15B	109.1
C8—N2—C11	119.4 (2)	H15A—C15—H15B	107.9
C14—N2—C11	110.2 (2)	N3—C12—C11	110.3 (3)
C7—C6—C5	120.4 (3)	N3—C12—H12A	109.6
C7—C6—H6	119.8	C11—C12—H12A	109.6
C5—C6—H6	119.8	N3—C12—H12B	109.6
C6—C7—F1	117.9 (3)	C11—C12—H12B	109.6
C6—C7—C8	123.4 (3)	H12A—C12—H12B	108.1
F1—C7—C8	118.7 (3)	N2—C11—C12	109.6 (3)
O3—C4—C2	125.4 (3)	N2—C11—H11A	109.7
O3—C4—C5	120.3 (3)	C12—C11—H11A	109.7
C2—C4—C5	114.4 (3)	N2—C11—H11B	109.7
N1—C1—C2	126.2 (3)	C12—C11—H11B	109.7
N1—C1—H1	116.9	H11A—C11—H11B	108.2
C2—C1—H1	116.9	N3—C13—C14	111.6 (3)
C1—C2—C4	119.2 (3)	N3—C13—H13A	109.3
C1—C2—C3	117.1 (3)	C14—C13—H13A	109.3
C4—C2—C3	123.7 (3)	N3—C13—H13B	109.3
C6—C5—C10	118.3 (3)	C14—C13—H13B	109.3
C6—C5—C4	119.1 (3)	H13A—C13—H13B	108.0
C10—C5—C4	122.5 (3)	C15—C16—H16A	109.5
O2—C3—O1	124.3 (3)	C15—C16—H16B	109.5
O2—C3—C2	119.1 (3)	H16A—C16—H16B	109.5
O1—C3—C2	116.7 (3)	C15—C16—H16C	109.5
N2—C14—C13	110.0 (3)	H16A—C16—H16C	109.5
N2—C14—H14A	109.7	H16B—C16—H16C	109.5
C13—C14—H14A	109.7	H4B—O4A—H4A	102 (6)
N2—C14—H14B	109.7
C10—C9—C8—N2	174.5 (3)	C5—C4—C2—C3	−176.7 (3)
C10—C9—C8—C7	−0.8 (4)	C7—C6—C5—C10	−0.3 (4)
C1—N1—C10—C9	−178.4 (3)	C7—C6—C5—C4	176.0 (3)
C15—N1—C10—C9	6.1 (4)	N1—C10—C5—C6	179.7 (3)
C1—N1—C10—C5	0.5 (4)	C9—C10—C5—C6	−1.4 (4)
C15—N1—C10—C5	−175.0 (3)	N1—C10—C5—C4	3.5 (4)
C8—C9—C10—N1	−179.1 (3)	C9—C10—C5—C4	−177.6 (3)
C8—C9—C10—C5	2.0 (4)	O3—C4—C5—C6	−0.7 (4)
C9—C8—N2—C14	−4.8 (4)	C2—C4—C5—C6	178.6 (3)
C7—C8—N2—C14	170.3 (3)	O3—C4—C5—C10	175.5 (3)
C9—C8—N2—C11	134.2 (3)	C2—C4—C5—C10	−5.2 (4)
C7—C8—N2—C11	−50.7 (4)	C1—C2—C3—O2	157.3 (3)
C5—C6—C7—F1	−175.1 (3)	C4—C2—C3—O2	−22.9 (5)
C5—C6—C7—C8	1.6 (5)	C1—C2—C3—O1	−22.6 (4)
C9—C8—C7—C6	−1.0 (4)	C4—C2—C3—O1	157.2 (3)
N2—C8—C7—C6	−176.4 (3)	C8—N2—C14—C13	−157.6 (3)
C9—C8—C7—F1	175.7 (3)	C11—N2—C14—C13	59.9 (3)
N2—C8—C7—F1	0.3 (4)	C1—N1—C15—C16	−86.4 (4)
C10—N1—C1—C2	−2.7 (5)	C10—N1—C15—C16	89.2 (4)
C15—N1—C1—C2	173.1 (3)	C13—N3—C12—C11	−54.6 (4)
N1—C1—C2—C4	0.7 (5)	C8—N2—C11—C12	156.3 (3)
N1—C1—C2—C3	−179.5 (3)	C14—N2—C11—C12	−61.6 (3)
O3—C4—C2—C1	−177.6 (3)	N3—C12—C11—N2	58.6 (4)
C5—C4—C2—C1	3.1 (4)	C12—N3—C13—C14	53.4 (4)
O3—C4—C2—C3	2.5 (5)	N2—C14—C13—N3	−55.8 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···O4A	0.90	1.88 (1)	2.741	160
N3—H3A···O4B	0.90	2.10 (1)	2.952	157
N3—H3B···O2i	0.90	1.99	2.777 (4)	145
N3—H3B···O3i	0.90	2.15	2.793 (4)	128
O4B—H4B···O1ii	0.912 (7)	2.02 (7)	2.793	141
O4A—H4A···O2iii	0.933 (10)	1.90 (9)	2.811	165

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3A⋯O4A	0.90	1.88 (1)	2.741	160
N3—H3A⋯O4B	0.90	2.10 (1)	2.952	157
N3—H3B⋯O2i	0.90	1.99	2.777 (4)	145
N3—H3B⋯O3i	0.90	2.15	2.793 (4)	128
O4B—H4B⋯O1ii	0.912 (7)	2.02 (7)	2.793	141
O4A—H4A⋯O2iii	0.933 (10)	1.90 (9)	2.811	165

Symmetry codes: (i) ; (ii) ; (iii) .