Norfloxacin sesquihydrate

Ravindra, N.V.; Panpalia, G.M.; Jagarlapudi, A.R.P.S.

doi:10.1107/S160053680900066X

organic compounds

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ISSN: 2056-9890

Volume 65| Part 2| February 2009| Page o303

doi:10.1107/S160053680900066X

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Norfloxacin sesquihydrate

Nittala V. Ravindra,^a Gopal M. Panpalia ^a and A. R. P. Sarma Jagarlapudi ^b ^*

^aBirla Institute of Technology, Department of Pharmaceutical Sciences, Mesra, Ranchi 835 215, India, and ^bGVK Biosciences Private Limited, S-1, Phase-1 Technocrats Industrial Estate, Balanagar, Hyderabad 500 037, India
^*Correspondence e-mail: sarma@gvkbio.com

(Received 20 November 2008; accepted 7 January 2009; online 14 January 2009)

In the crystal structure of the title compound [systematic name: 1-ethyl-6-fluoro-4-oxo-7-(piperazin-4-ium-1-yl)-1,4-dihydroquinoline-3-carboxylate sesquihydrate], C₁₆H₁₈FN₃O₃·1.42H₂O, N—H⋯O and O—H⋯O hydrogen bonds assemble the molecules in a two-dimensional layered corrugated sheet structure parallel to the b axis. The water molecules 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_r = 344.12
Monoclinic, P 2₁ /c
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[F² > 2σ(F²)] = 0.081
wR(F²) = 0.218
S = 1.03
3228 reflections
253 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.37 e Å⁻³
Δρ_min = −0.26 e Å⁻³

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) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[-x+1, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (iii) $[x-1, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ .

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.

Supporting information

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

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

checkCIF report

Comment top

Norfloxacin (NF) is a broad spectrum 4-fluoroquinolone antibacterial used in the treatment of urinary tract infections. As part of our interest in polymorphs and hydrates of NF, we have investigated the crystal structure of NF sesquihydrate, (I) (Fig. 1). NF molecule is zwitterionic and the N3 nitrogen is protonated similar to the reported structure of dihydrate (Florence et al., 2000) and anhydrous zwitterion (Barbas et al., 2007). The molecules are linked via N—H···O and O—H···O hydrogen bonds, forming two-dimensional corrugated sheets parallel to b axis. These sheets are linked together by the water molecules which act as acceptors of H atoms, assembling the molecules in an infinite two-dimensional network (Fig. 2).

Related literature top

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 top

The title compound was prepared from anhydrous form as reported by Katdare et al.,(1986). It was then dissolved in Acetonitrile on water bath and allowed to cool in sealed flask. Pale yellow colored block like crystals suitable for x-ray analysis appeared after two days.

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of (I), with atom labels and 50% probability displacement ellipsoids for non-H atoms. Labels for Hydrogen atoms have been omitted for clarity.
	Fig. 2. The packing of (I), showing the corrugated sheet layers of molecules parallel to b axis and water molecules connected by N—H···O and O—H···O hydrogen bonds (dashed lines).

1-ethyl-6-fluoro-4-oxo-7-(piperazin-4-ium-1-yl)-1,4-dihydroquinoline-3- carboxylate sesquihydrate top

Crystal data top

C₁₆H₁₈FN₃O₃·1.42H₂O	F(000) = 725.5
M_r = 344.12	D_x = 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

Data collection top

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

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)] = 0.081	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(F_o²) + (0.1124P)² + 1.8021P] where P = (F_o² + 2F_c²)/3
3228 reflections	(Δ/σ)_max < 0.001
253 parameters	Δρ_max = 0.37 e Å⁻³
0 restraints	Δρ_min = −0.26 e Å⁻³

Crystal data top

C₁₆H₁₈FN₃O₃·1.42H₂O	V = 1630.2 (7) Å³
M_r = 344.12	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 8.8434 (18) Å	µ = 0.11 mm⁻¹
b = 22.312 (5) Å	T = 298 K
c = 8.7564 (18) Å	0.20 × 0.20 × 0.10 mm
β = 109.35 (3)°

Data collection top

Bruker SMART CCD area-detector diffractometer	2553 reflections with I > 2σ(I)
16819 measured reflections	R_int = 0.044
3228 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.081	0 restraints
wR(F²) = 0.218	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.37 e Å⁻³
3228 reflections	Δρ_min = −0.26 e Å⁻³
253 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	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)*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x+1, y−1/2, −z+1/2; (ii) −x+1, y−1/2, −z+3/2; (iii) x−1, −y+3/2, z−1/2.

Experimental details

Crystal data
Chemical formula	C₁₆H₁₈FN₃O₃·1.42H₂O
M_r	344.12
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	8.8434 (18), 22.312 (5), 8.7564 (18)
β (°)	109.35 (3)
V (Å³)	1630.2 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.20 × 0.20 × 0.10

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	16819, 3228, 2553
R_int	0.044
(sin θ/λ)_max (Å⁻¹)	0.618

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.081, 0.218, 1.03
No. of reflections	3228
No. of parameters	253
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.37, −0.26

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···O4A	0.900	1.878 (4)	2.741	160
N3—H3A···O4B	0.900	2.102 (3)	2.952	157
N3—H3B···O2ⁱ	0.900	1.990	2.777 (4)	145
N3—H3B···O3ⁱ	0.900	2.1500	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) −x+1, y−1/2, −z+1/2; (ii) −x+1, y−1/2, −z+3/2; (iii) x−1, −y+3/2, z−1/2.

Acknowledgements

NVR thanks the Birla Institute of Technology for financial support. NVR also thanks Jagadeesh Babu and Professor Ashwini Nangia, University of Hyderabad, for help in X-ray diffraction.

References

Barbas, R., Martí, F., Prohens, R. & Puigjaner, C. (2006). Cryst. Growth Des. 6, 1463–1467. Web of Science CrossRef CAS Google Scholar
Barbas, R., Prohens, R. & Puigjaner, C. (2007). J. Therm. Anal. Calorim. 89, 687–692. Web of Science CSD 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 (1997). SMART and SAINT. Bruker AXS Inc.,Madison, Wisconsin, USA. Google Scholar
Chongcharoen, W., Byrn, S. R. & Sutanthavibul, N. (2008). J. Pharm. Sci. 97, 473–489. Web of Science CrossRef PubMed CAS Google Scholar
Florence, A. J., Kennedy, A. R., Shankland, N., Wright, E. & Al-Rubayi, A. (2000). Acta Cryst. C56, 1372–1373. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Katdare, A. V., Ryan, J. A., Bavitz, J. F., Erb, D. M. & Guillory, J. K. (1986). Mikrochim. Acta Wien III, 90, 1–12. CrossRef Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Šuštar, B., Bukovec, N. & Bukovec, P. (1993). J. Therm. Anal. 40, 475–481. Google Scholar
Windholz, M., Budavari, S., Blumetti, R. F. & Otterbein, E. S. (1983). Editors. The Merck Index, 10th ed. Rahway, NJ, USA: Merck and Co. Inc. Google Scholar
Yuasa, R., Imai, J., Morikawa, H., Kusajima, H., Uchida, H. & Irikura, T. (1982). Yakugaku Zasshi, 102, 469–476. CAS PubMed Web of Science Google Scholar