Sparfloxacin, an antibacterial drug

Sivalakshmidevi, A.; Vyas, K.; Om Reddy, G.

doi:10.1107/S0108270100002523

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Sparfloxacin, an antibacterial drug

A. Sivalakshmidevi, K. Vyas and G. Om Reddy

The title compound, sparfloxacin or cis-5-amino-1-cyclopropyl-7-(3,5-dimethylpiperazin-1-yl)-6,8-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid trihydrate, C₁₉H₂₂F₂N₄O₃·3H₂O, is an antibacterial drug. The molecule, which crystallizes as a trihydrate, is in the zwitterionic form in the solid state. Hydrogen bonds stabilize the molecules in the lattice.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270100002523/qa0214sup1.cif Contains datablocks SPARFLOXACIN, I
	Structure factor file (CIF format) https://doi.org/10.1107/S0108270100002523/qa0214Isup2.hkl Contains datablock I

CCDC reference: 143343

Comment top

Fluorinated quinolones are extensively used as antibacterial agents. X-ray diffraction studies of the title compound, (I), have been undertaken as part of a structural elucidation project. All the bond lengths and angles are normal (Allen et al., 1987). The piperazine ring assumes a chair form as evidenced by the torsion angles. The relevant asymmetry parameters are ΔC2 = 1.8, 1.51 and 1.6, and ΔC_s = 1.06, 2.21 and 3.08 (Duax et al., 1976). The weight loss of 11.5% in the thermogravimetric analysis experiment indicates the presence of three molecules of water. The N2 atom of the amino group is involved in intramolecular hydrogen bonding with the O3 atom of the carbonyl group of the quinolone moiety.

Three intermolecular hydrogen-bonding interactions viz., molecule–molecule, molecule–water and water–water, stabilize the molecules in the lattice. Donating its two H atoms, the protonated amino piperazine N4 atom is involved in hydrogen bonding with the quinolone carbonyl O3 atom and the the O2 atom of the caboxylate group. The amino N2 atom interacts with the O1 atom of the carboxylate group. Both the water molecules O4 and O6 have hydrogen-bond interactions with the carboxylate O1 and O2' atoms. The water O5 atom donates a H atom to the water O4 and O6 atoms and, in addition, accepts a H atom from the piperazine N4 atom to form a hydrogen bond. Hydrogen-bonding parameters are presented in Table 2.

Experimental top

Crystals of Sparfloxacin suitable for X-ray diffraction were grown from a mixture of ethyl acetate, chloroform and acetone.

Computing details top

Data collection: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1994); cell refinement: MSC/AFC Diffractometer Control Software; data reduction: TEXSAN (Molecular Structure Corporation, 1995); program(s) used to solve structure: SIR92 (Altomare, et al. 1993); program(s) used to refine structure: TEXSAN; software used to prepare material for publication: TEXSAN.

(I) top

Crystal data top

C₁₉H₂₂F₂N₄O₃·3H₂O	F(000) = 944.00
M_r = 446.45	D_x = 1.375 Mg m⁻³
Monoclinic, P2₁/n	Cu Kα radiation, λ = 1.5418 Å
a = 11.850 (3) Å	Cell parameters from 25 reflections
b = 10.913 (4) Å	θ = 25.0–30.9°
c = 17.506 (2) Å	µ = 0.97 mm⁻¹
β = 107.76 (1)°	T = 298 K
V = 2156.0 (8) Å³	Needle, colourless
Z = 4	0.50 × 0.50 × 0.25 mm

Data collection top

Rigaku AFC-7S diffractometer	4260 reflections with I > 1.2σ(I)
Radiation source: X-ray tube	R_int = 0.036
Graphite monochromator	θ_max = 70.1°, θ_min = 2.7°
ω–2θ scans	h = 0→14
Absorption correction: ψ scan (North et al., 1968)	k = 0→13
T_min = 0.872, T_max = 1.000	l = −21→20
4480 measured reflections	3 standard reflections every 150 reflections
4479 independent reflections	intensity decay: −0.3%

Refinement top

Refinement on F	0 constraints
Least-squares matrix: full	All H-atom parameters refined
R[F² > 2σ(F²)] = 0.059	Weighting scheme based on measured s.u.'s w = 1/[σ²(F_o) + 0.00016\|F_o\|²]
wR(F²) = 0.108	(Δ/σ)_max = 0.004
S = 1.91	Δρ_max = 0.30 e Å⁻³
3550 reflections	Δρ_min = −0.27 e Å⁻³
393 parameters	Extinction correction: Zachariasen (1967)
0 restraints	Extinction coefficient: 6E-6 (1)

Crystal data top

C₁₉H₂₂F₂N₄O₃·3H₂O	V = 2156.0 (8) Å³
M_r = 446.45	Z = 4
Monoclinic, P2₁/n	Cu Kα radiation
a = 11.850 (3) Å	µ = 0.97 mm⁻¹
b = 10.913 (4) Å	T = 298 K
c = 17.506 (2) Å	0.50 × 0.50 × 0.25 mm
β = 107.76 (1)°

Data collection top

Rigaku AFC-7S diffractometer	4260 reflections with I > 1.2σ(I)
Absorption correction: ψ scan (North et al., 1968)	R_int = 0.036
T_min = 0.872, T_max = 1.000	3 standard reflections every 150 reflections
4480 measured reflections	intensity decay: −0.3%
4479 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.059	0 restraints
wR(F²) = 0.108	All H-atom parameters refined
S = 1.91	Δρ_max = 0.30 e Å⁻³
3550 reflections	Δρ_min = −0.27 e Å⁻³
393 parameters

Special details top

Experimental. The scan width was (0.94 + 0.14tanθ)° with an ω scan speed of 16° per minute (up to 5 scans to achieve I/σ(I) > 15). Stationary background counts were recorded at each end of the scan, and the scan time:background time ratio was 2:1.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
F1	0.5536 (1)	0.1366 (2)	0.6687 (1)	0.0553 (5)
F2	0.5117 (1)	0.2627 (2)	0.40512 (9)	0.0558 (5)
O1	1.1641 (1)	0.1645 (2)	0.7640 (1)	0.0475 (5)
O2	1.1473 (1)	0.3193 (2)	0.6782 (1)	0.0498 (5)
O3	0.9540 (1)	0.2645 (2)	0.5411 (1)	0.0438 (5)
O4	1.1184 (2)	−0.0854 (2)	0.7664 (2)	0.0647 (6)
O5	0.0472 (3)	0.2079 (3)	0.3574 (2)	0.0822 (8)
O6	1.4014 (2)	0.0843 (3)	0.8150 (3)	0.107 (1)
N1	0.8034 (2)	0.1252 (2)	0.7034 (1)	0.0358 (5)
N2	0.7455 (2)	0.2814 (2)	0.4337 (1)	0.0452 (6)
N3	0.4087 (2)	0.2078 (2)	0.5258 (2)	0.0515 (6)
N4	0.1730 (2)	0.2355 (2)	0.5221 (1)	0.0383 (5)
C1	0.9204 (2)	0.1496 (2)	0.7230 (1)	0.0359 (5)
C2	0.9744 (2)	0.2049 (2)	0.6743 (1)	0.0330 (5)
C3	0.9074 (2)	0.2298 (2)	0.5922 (1)	0.0338 (5)
C4	0.7793 (2)	0.2112 (2)	0.5711 (1)	0.0318 (5)
C5	0.7282 (2)	0.1643 (2)	0.6293 (1)	0.0331 (5)
C6	0.6054 (2)	0.1623 (2)	0.6113 (1)	0.0397 (6)
C7	0.5300 (2)	0.2001 (2)	0.5377 (1)	0.0397 (6)
C8	0.5823 (2)	0.2353 (2)	0.4803 (1)	0.0400 (6)
C9	0.7037 (2)	0.2438 (2)	0.4933 (1)	0.0352 (5)
C10	0.3402 (2)	0.0994 (2)	0.5318 (2)	0.0446 (7)
C11	0.2448 (2)	0.1316 (2)	0.5691 (2)	0.0410 (6)
C12	0.2458 (2)	0.3458 (2)	0.5177 (2)	0.0428 (6)
C13	0.3385 (2)	0.3069 (3)	0.4794 (2)	0.0485 (7)
C14	0.1668 (3)	0.4469 (3)	0.4709 (2)	0.0563 (8)
C15	0.1643 (3)	0.0248 (3)	0.5701 (2)	0.0573 (9)
C16	0.7599 (2)	0.0576 (2)	0.7602 (1)	0.0433 (6)
C17	0.7126 (3)	−0.0678 (3)	0.7398 (2)	0.069 (1)
C18	0.8301 (3)	−0.0494 (3)	0.8031 (2)	0.0630 (9)
C19	1.1059 (2)	0.2320 (2)	0.7082 (1)	0.0366 (5)
H1	0.961 (3)	0.124 (3)	0.774 (2)	0.062 (9)*
H2	0.827 (3)	0.284 (3)	0.449 (2)	0.043 (7)*
H3	0.698 (3)	0.293 (3)	0.386 (2)	0.054 (8)*
H4	0.391 (3)	0.042 (3)	0.562 (2)	0.060 (9)*
H5	0.299 (3)	0.068 (4)	0.476 (2)	0.066 (9)*
H6	0.285 (2)	0.166 (3)	0.626 (2)	0.039 (6)*
H7	0.132 (3)	0.213 (3)	0.469 (2)	0.040 (7)*
H8	0.125 (4)	0.252 (3)	0.545 (2)	0.07 (1)*
H9	0.280 (3)	0.368 (3)	0.570 (2)	0.061 (9)*
H10	0.298 (3)	0.280 (3)	0.425 (2)	0.052 (8)*
H11	0.398 (3)	0.372 (4)	0.473 (2)	0.07 (1)*
H12	0.217 (3)	0.519 (3)	0.467 (2)	0.056 (8)*
H13	0.127 (4)	0.418 (4)	0.419 (3)	0.09 (1)*
H14	0.112 (4)	0.468 (4)	0.494 (3)	0.10 (1)*
H15	0.126 (3)	0.003 (4)	0.524 (2)	0.07 (1)*
H16	0.100 (4)	0.052 (5)	0.597 (3)	0.11 (1)*
H17	0.222 (4)	−0.053 (5)	0.605 (3)	0.11 (1)*
H18	0.720 (3)	0.117 (4)	0.789 (2)	0.07 (1)*
H19	0.713 (4)	−0.102 (4)	0.685 (3)	0.09 (1)*
H20	0.634 (4)	−0.078 (4)	0.752 (3)	0.08 (1)*
H21	0.837 (4)	−0.058 (4)	0.856 (3)	0.08 (1)*
H22	0.896 (4)	−0.067 (5)	0.787 (3)	0.10 (1)*
H23	1.137 (4)	−0.004 (4)	0.759 (2)	0.08 (1)*
H24	1.196 (5)	−0.123 (5)	0.767 (3)	0.10 (1)*
H25	1.399 (4)	0.002 (5)	0.827 (3)	0.11 (1)*
H26	1.324 (5)	0.111 (5)	0.785 (3)	0.11 (1)*
H27	0.008 (5)	0.277 (5)	0.341 (4)	0.12 (2)*
H28	0.001 (4)	0.158 (5)	0.333 (3)	0.10 (1)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
F1	0.0403 (8)	0.081 (1)	0.0536 (9)	0.0009 (7)	0.0284 (7)	0.0138 (7)
F2	0.0307 (7)	0.089 (1)	0.0416 (8)	0.0021 (7)	0.0024 (6)	0.0141 (7)
O1	0.0360 (9)	0.057 (1)	0.0422 (9)	0.0025 (7)	0.0010 (7)	0.0032 (7)
O2	0.0373 (9)	0.052 (1)	0.056 (1)	−0.0105 (7)	0.0080 (8)	0.0018 (8)
O3	0.0278 (8)	0.068 (1)	0.0367 (8)	−0.0006 (7)	0.0123 (6)	0.0103 (7)
O4	0.046 (1)	0.056 (1)	0.083 (2)	0.0034 (9)	0.006 (1)	0.002 (1)
O5	0.078 (2)	0.078 (2)	0.066 (1)	0.006 (1)	−0.014 (1)	−0.014 (1)
O6	0.045 (1)	0.068 (2)	0.187 (4)	−0.003 (1)	0.006 (2)	0.007 (2)
N1	0.036 (1)	0.041 (1)	0.0322 (9)	−0.0011 (7)	0.0127 (7)	0.0034 (7)
N2	0.032 (1)	0.073 (1)	0.030 (1)	−0.0016 (9)	0.0078 (8)	0.0088 (9)
N3	0.025 (1)	0.052 (1)	0.078 (2)	0.0033 (8)	0.017 (1)	0.016 (1)
N4	0.0280 (9)	0.047 (1)	0.043 (1)	−0.0006 (8)	0.0149 (9)	−0.0025 (8)
C1	0.035 (1)	0.038 (1)	0.032 (1)	0.0004 (8)	0.0061 (8)	0.0008 (8)
C2	0.029 (1)	0.035 (1)	0.034 (1)	0.0001 (8)	0.0086 (8)	−0.0033 (8)
C3	0.029 (1)	0.037 (1)	0.036 (1)	0.0009 (8)	0.0100 (8)	−0.0002 (8)
C4	0.028 (1)	0.037 (1)	0.030 (1)	0.0005 (7)	0.0089 (8)	−0.0006 (8)
C5	0.031 (1)	0.036 (1)	0.034 (1)	−0.0013 (8)	0.0117 (8)	0.0004 (8)
C6	0.034 (1)	0.047 (1)	0.043 (1)	−0.0022 (9)	0.0193 (9)	0.0040 (9)
C7	0.028 (1)	0.043 (1)	0.050 (1)	0.0006 (9)	0.0131 (9)	0.002 (1)
C8	0.029 (1)	0.052 (1)	0.037 (1)	0.0007 (9)	0.0054 (9)	0.0058 (9)
C9	0.029 (1)	0.041 (1)	0.035 (1)	−0.0018 (8)	0.0082 (9)	−0.0010 (8)
C10	0.033 (1)	0.043 (1)	0.062 (2)	0.0014 (9)	0.021 (1)	0.002 (1)
C11	0.035 (1)	0.042 (1)	0.048 (1)	−0.0025 (9)	0.017 (1)	0.0008 (9)
C12	0.035 (1)	0.045 (1)	0.046 (1)	−0.0039 (9)	0.009 (1)	−0.001 (1)
C13	0.032 (1)	0.054 (1)	0.063 (2)	0.005 (1)	0.019 (1)	0.015 (1)
C14	0.044 (1)	0.048 (1)	0.079 (2)	0.006 (1)	0.021 (1)	0.007 (1)
C15	0.048 (1)	0.046 (1)	0.087 (2)	−0.007 (1)	0.034 (2)	−0.003 (1)
C16	0.048 (1)	0.049 (1)	0.036 (1)	−0.002 (1)	0.018 (1)	0.0081 (9)
C17	0.081 (2)	0.059 (2)	0.067 (2)	−0.019 (2)	0.023 (2)	0.008 (1)
C18	0.072 (2)	0.059 (2)	0.061 (2)	0.004 (1)	0.025 (2)	0.023 (1)
C19	0.031 (1)	0.042 (1)	0.034 (1)	−0.0003 (8)	0.0062 (9)	−0.0061 (8)

Geometric parameters (Å, º) top

F1—C6	1.356 (3)	C4—C9	1.429 (3)
F2—C8	1.360 (3)	C5—C6	1.393 (3)
O1—C19	1.250 (3)	C6—C7	1.388 (3)
O2—C19	1.257 (3)	C7—C8	1.385 (3)
O3—C3	1.245 (3)	C8—C9	1.389 (3)
O4—H23	0.93 (5)	C10—C11	1.510 (3)
O4—H24	1.00 (5)	C10—H4	0.91 (3)
O5—H27	0.89 (6)	C10—H5	1.00 (4)
O5—H28	0.80 (5)	C11—C15	1.509 (3)
O6—H25	0.92 (6)	C11—H6	1.04 (3)
O6—H26	0.95 (5)	C12—C13	1.512 (4)
N1—C1	1.349 (3)	C12—C14	1.515 (4)
N1—C5	1.398 (3)	C12—H9	0.92 (4)
N1—C16	1.453 (3)	C13—H10	0.97 (3)
N2—C9	1.348 (3)	C13—H11	1.03 (4)
N2—H2	0.92 (3)	C14—H12	1.00 (3)
N2—H3	0.86 (3)	C14—H13	0.94 (5)
N3—C7	1.391 (3)	C14—H14	0.90 (5)
N3—C10	1.456 (3)	C15—H15	0.83 (4)
N3—C13	1.452 (3)	C15—H16	1.04 (5)
N4—C11	1.504 (3)	C15—H17	1.14 (5)
N4—C12	1.496 (3)	C16—C17	1.481 (4)
N4—H7	0.94 (3)	C16—C18	1.497 (4)
N4—H8	0.81 (4)	C16—H18	1.02 (4)
C1—C2	1.354 (3)	C17—C18	1.505 (5)
C1—H1	0.92 (3)	C17—H19	1.03 (5)
C2—C3	1.440 (3)	C17—H20	1.02 (4)
C2—C19	1.518 (3)	C18—H21	0.91 (4)
C3—C4	1.462 (3)	C18—H22	0.93 (5)
C4—C5	1.430 (3)

H23—O4—H24	98 (4)	N4—C11—C10	108.1 (2)
H27—O5—H28	102 (5)	N4—C11—C15	109.6 (2)
H25—O6—H26	110 (4)	N4—C11—H6	106 (2)
C1—N1—C5	119.3 (2)	C10—C11—C15	112.7 (2)
C1—N1—C16	118.6 (2)	C10—C11—H6	109 (2)
C5—N1—C16	122.1 (2)	C15—C11—H6	112 (2)
C9—N2—H2	112 (2)	N4—C12—C13	107.8 (2)
C9—N2—H3	120 (2)	N4—C12—C14	110.0 (2)
H2—N2—H3	127 (3)	N4—C12—H9	104 (2)
C7—N3—C10	120.9 (2)	C13—C12—C14	112.2 (2)
C7—N3—C13	121.2 (2)	C13—C12—H9	111 (2)
C10—N3—C13	114.1 (2)	C14—C12—H9	111 (2)
C11—N4—C12	113.3 (2)	N3—C13—C12	109.3 (2)
C11—N4—H7	112 (2)	N3—C13—H10	110 (2)
C11—N4—H8	105 (3)	N3—C13—H11	106 (2)
C12—N4—H7	107 (2)	C12—C13—H10	108 (2)
C12—N4—H8	111 (3)	C12—C13—H11	118 (2)
H7—N4—H8	108 (3)	H10—C13—H11	104 (3)
N1—C1—C2	125.1 (2)	C12—C14—H12	109 (2)
N1—C1—H1	112 (2)	C12—C14—H13	108 (3)
C2—C1—H1	123 (2)	C12—C14—H14	111 (3)
C1—C2—C3	119.3 (2)	H12—C14—H13	110 (3)
C1—C2—C19	117.8 (2)	H12—C14—H14	111 (4)
C3—C2—C19	122.8 (2)	H13—C14—H14	108 (4)
O3—C3—C2	122.9 (2)	C11—C15—H15	112 (3)
O3—C3—C4	121.0 (2)	C11—C15—H16	109 (3)
C2—C3—C4	116.1 (2)	C11—C15—H17	108 (2)
C3—C4—C5	120.2 (2)	H15—C15—H16	105 (4)
C3—C4—C9	120.5 (2)	H15—C15—H17	111 (4)
C5—C4—C9	119.3 (2)	H16—C15—H17	112 (4)
N1—C5—C4	118.8 (2)	N1—C16—C17	119.4 (2)
N1—C5—C6	122.1 (2)	N1—C16—C18	118.7 (2)
C4—C5—C6	119.0 (2)	N1—C16—H18	109 (2)
F1—C6—C5	120.9 (2)	C17—C16—C18	60.7 (2)
F1—C6—C7	116.2 (2)	C17—C16—H18	121 (2)
C5—C6—C7	122.5 (2)	C18—C16—H18	121 (2)
N3—C7—C6	119.9 (2)	C16—C17—C18	60.1 (2)
N3—C7—C8	123.0 (2)	C16—C17—H19	117 (3)
C6—C7—C8	116.9 (2)	C16—C17—H20	111 (2)
F2—C8—C7	118.9 (2)	C18—C17—H19	118 (2)
F2—C8—C9	116.4 (2)	C18—C17—H20	124 (2)
C7—C8—C9	124.7 (2)	H19—C17—H20	115 (3)
N2—C9—C4	122.8 (2)	C16—C18—C17	59.1 (2)
N2—C9—C8	120.0 (2)	C16—C18—H21	117 (3)
C4—C9—C8	117.1 (2)	C16—C18—H22	114 (3)
N3—C10—C11	110.5 (2)	C17—C18—H21	121 (3)
N3—C10—H4	108 (2)	C17—C18—H22	115 (3)
N3—C10—H5	109 (2)	H21—C18—H22	117 (4)
C11—C10—H4	111 (2)	O1—C19—O2	125.5 (2)
C11—C10—H5	107 (2)	O1—C19—C2	116.5 (2)
H4—C10—H5	111 (3)	O2—C19—C2	118.0 (2)

F1—C6—C5—N1	9.0 (5)	C1—N1—C5—C6	−168.1 (3)
F1—C6—C5—C4	−169.6 (3)	C1—N1—C16—C17	−112.6 (4)
F1—C6—C7—N3	−1.1 (5)	C1—N1—C16—C18	−41.9 (5)
F1—C6—C7—C8	175.2 (3)	C1—C2—C3—C4	9.7 (4)
F2—C8—C7—N3	−9.4 (5)	C2—C1—N1—C5	−4.0 (5)
F2—C8—C7—C6	174.5 (3)	C2—C1—N1—C16	175.9 (3)
F2—C8—C9—N2	1.6 (5)	C2—C3—C4—C5	−3.3 (4)
F2—C8—C9—C4	−178.0 (3)	C2—C3—C4—C9	174.4 (3)
O1—C19—C2—C1	26.0 (4)	C3—C4—C5—C6	172.0 (3)
O1—C19—C2—C3	−150.8 (3)	C3—C4—C9—C8	−173.7 (3)
O2—C19—C2—C1	−153.8 (3)	C4—C3—C2—C19	−173.5 (3)
O2—C19—C2—C3	29.4 (4)	C4—C5—N1—C16	−169.5 (3)
O3—C3—C2—C1	−169.6 (3)	C4—C5—C6—C7	2.1 (5)
O3—C3—C2—C19	7.2 (5)	C4—C9—C8—C7	1.6 (5)
O3—C3—C4—C5	176.0 (3)	C5—N1—C16—C17	67.3 (5)
O3—C3—C4—C9	−6.3 (4)	C5—N1—C16—C18	138.0 (4)
N1—C1—C2—C3	−6.5 (5)	C5—C4—C9—C8	3.9 (4)
N1—C1—C2—C19	176.6 (3)	C5—C6—C7—C8	3.1 (5)
N1—C5—C4—C3	−6.6 (4)	C6—C5—N1—C16	12.0 (4)
N1—C5—C4—C9	175.7 (3)	C6—C5—C4—C9	−5.7 (4)
N1—C5—C6—C7	−179.4 (3)	C6—C7—N3—C10	−62.2 (5)
N1—C16—C17—C18	108.4 (4)	C6—C7—N3—C13	141.1 (4)
N1—C16—C18—C17	−109.8 (4)	C6—C7—C8—C9	−5.1 (5)
N2—C9—C4—C3	6.7 (5)	C7—N3—C10—C11	143.4 (3)
N2—C9—C4—C5	−175.7 (3)	C7—N3—C13—C12	−142.4 (3)
N2—C9—C8—C7	−178.8 (3)	C8—C7—N3—C10	121.7 (4)
N3—C7—C6—C5	−173.2 (3)	C8—C7—N3—C13	−34.9 (5)
N3—C7—C8—C9	171.1 (3)	C10—N3—C13—C12	59.5 (4)
N3—C10—C11—N4	54.1 (4)	C10—C11—N4—C12	−56.7 (4)
N3—C10—C11—C15	175.3 (3)	C11—N4—C12—C13	58.2 (4)
N3—C13—C12—N4	−56.7 (4)	C11—N4—C12—C14	−178.6 (3)
N3—C13—C12—C14	−178.2 (3)	C11—C10—N3—C13	−58.4 (4)
C1—N1—C5—C4	10.4 (4)	C12—N4—C11—C15	−179.7 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O4—H23···O1	0.93 (5)	1.87 (5)	2.784 (3)	168 (4)
O4—H24···O2ⁱ	1.00 (5)	1.92 (5)	2.845 (3)	152 (4)
O5—H27···O6ⁱⁱ	0.89 (6)	1.94 (6)	2.810 (4)	168 (6)
O5—H28···O4ⁱⁱⁱ	0.80	2.04	2.781 (4)	155
O6—H25···O2ⁱ	0.92 (6)	2.06 (6)	2.959 (4)	163 (5)
O6—H26···O1	0.95 (5)	1.91 (5)	2.818 (3)	159 (5)
N2—H2···O3	0.92 (3)	1.85 (3)	2.616 (2)	139 (3)
N2—H3···O1^iv	0.86 (3)	2.11 (3)	2.890 (3)	151 (3)
N4—H7···O5	0.94 (3)	1.91 (3)	2.829 (3)	166 (3)
N4—H8···O3^v	0.81 (4)	2.01 (4)	2.733 (2)	148 (4)
N4—H8···O2^v	0.81 (4)	2.38 (4)	2.985 (3)	132 (3)

Symmetry codes: (i) −x+5/2, y−1/2, −z+3/2; (ii) x−3/2, −y+1/2, z−1/2; (iii) −x+1, −y, −z+1; (iv) x−1/2, −y+1/2, z−1/2; (v) x−1, y, z.

Experimental details

Crystal data
Chemical formula	C₁₉H₂₂F₂N₄O₃·3H₂O
M_r	446.45
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	298
a, b, c (Å)	11.850 (3), 10.913 (4), 17.506 (2)
β (°)	107.76 (1)
V (Å³)	2156.0 (8)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	0.97
Crystal size (mm)	0.50 × 0.50 × 0.25

Data collection
Diffractometer	Rigaku AFC-7S diffractometer
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.872, 1.000
No. of measured, independent and observed [I > 1.2σ(I)] reflections	4480, 4479, 4260
R_int	0.036
(sin θ/λ)_max (Å⁻¹)	0.610

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.059, 0.108, 1.91
No. of reflections	3550
No. of parameters	393
H-atom treatment	All H-atom parameters refined
Δρ_max, Δρ_min (e Å⁻³)	0.30, −0.27

Computer programs: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1994), MSC/AFC Diffractometer Control Software, TEXSAN (Molecular Structure Corporation, 1995), SIR92 (Altomare, et al. 1993), TEXSAN.

Selected geometric parameters (Å, º) top

F1—C6	1.356 (3)	C2—C19	1.518 (3)
F2—C8	1.360 (3)	C3—C4	1.462 (3)
O1—C19	1.250 (3)	C4—C5	1.430 (3)
O2—C19	1.257 (3)	C4—C9	1.429 (3)
O3—C3	1.245 (3)	C5—C6	1.393 (3)
N1—C1	1.349 (3)	C6—C7	1.388 (3)
N1—C5	1.398 (3)	C7—C8	1.385 (3)
N1—C16	1.453 (3)	C8—C9	1.389 (3)
N2—C9	1.348 (3)	C10—C11	1.510 (3)
N3—C7	1.391 (3)	C11—C15	1.509 (3)
N3—C10	1.456 (3)	C12—C13	1.512 (4)
N3—C13	1.452 (3)	C12—C14	1.515 (4)
N4—C11	1.504 (3)	C16—C17	1.481 (4)
N4—C12	1.496 (3)	C16—C18	1.497 (4)
C1—C2	1.354 (3)	C17—C18	1.505 (5)
C2—C3	1.440 (3)

C1—N1—C5	119.3 (2)	N3—C7—C8	123.0 (2)
C1—N1—C16	118.6 (2)	C6—C7—C8	116.9 (2)
C5—N1—C16	122.1 (2)	F2—C8—C7	118.9 (2)
C7—N3—C10	120.9 (2)	F2—C8—C9	116.4 (2)
C7—N3—C13	121.2 (2)	C7—C8—C9	124.7 (2)
C10—N3—C13	114.1 (2)	N2—C9—C4	122.8 (2)
C11—N4—C12	113.3 (2)	N2—C9—C8	120.0 (2)
N1—C1—C2	125.1 (2)	C4—C9—C8	117.1 (2)
C1—C2—C3	119.3 (2)	N3—C10—C11	110.5 (2)
C1—C2—C19	117.8 (2)	N4—C11—C10	108.1 (2)
C3—C2—C19	122.8 (2)	N4—C11—C15	109.6 (2)
O3—C3—C2	122.9 (2)	C10—C11—C15	112.7 (2)
O3—C3—C4	121.0 (2)	N4—C12—C13	107.8 (2)
C2—C3—C4	116.1 (2)	N4—C12—C14	110.0 (2)
C3—C4—C5	120.2 (2)	C13—C12—C14	112.2 (2)
C3—C4—C9	120.5 (2)	N3—C13—C12	109.3 (2)
C5—C4—C9	119.3 (2)	N1—C16—C17	119.4 (2)
N1—C5—C4	118.8 (2)	N1—C16—C18	118.7 (2)
N1—C5—C6	122.1 (2)	C17—C16—C18	60.7 (2)
C4—C5—C6	119.0 (2)	C16—C17—C18	60.1 (2)
F1—C6—C5	120.9 (2)	C16—C18—C17	59.1 (2)
F1—C6—C7	116.2 (2)	O1—C19—O2	125.5 (2)
C5—C6—C7	122.5 (2)	O1—C19—C2	116.5 (2)
N3—C7—C6	119.9 (2)	O2—C19—C2	118.0 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O4—H23···O1	0.93 (5)	1.87 (5)	2.784 (3)	168 (4)
O4—H24···O2ⁱ	1.00 (5)	1.92 (5)	2.845 (3)	152 (4)
O5—H27···O6ⁱⁱ	0.89 (6)	1.94 (6)	2.810 (4)	168 (6)
O5—H28···O4ⁱⁱⁱ	0.80	2.04	2.781 (4)	155.3
O6—H25···O2ⁱ	0.92 (6)	2.06 (6)	2.959 (4)	163 (5)
O6—H26···O1	0.95 (5)	1.91 (5)	2.818 (3)	159 (5)
N2—H2···O3	0.92 (3)	1.85 (3)	2.616 (2)	139 (3)
N2—H3···O1^iv	0.86 (3)	2.11 (3)	2.890 (3)	151 (3)
N4—H7···O5	0.94 (3)	1.91 (3)	2.829 (3)	166 (3)
N4—H8···O3^v	0.81 (4)	2.01 (4)	2.733 (2)	148 (4)
N4—H8···O2^v	0.81 (4)	2.38 (4)	2.985 (3)	132 (3)

Symmetry codes: (i) −x+5/2, y−1/2, −z+3/2; (ii) x−3/2, −y+1/2, z−1/2; (iii) −x+1, −y, −z+1; (iv) x−1/2, −y+1/2, z−1/2; (v) x−1, y, z.

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