Marbofloxacin.

IN THE TITLE COMPOUND, [SYSTEMATIC NAME: 9-fluoro-2,3-dihydro-3-methyl-10-(4-methyl-piperazin-1-yl)-7-oxo-7H-pyrido[1,2,3-ij][1,2,4]benzoxadiazine-6-carb-oxy-lic acid], C(17)H(19)FN(4)O(4), the carbonyl and carboxyl groups are coplanar with the quinoline ring, making a dihedral angle of 2.39 (2)°. The piperazine ring adopts a chair conformation and the oxadiazinane ring displays an envelope conformation with the CH(2) group at the flap displaced by 0.650 (2) Å from the plane through the other five atoms. The mol-ecular structure exhibits an S(6) ring motif, owing to an intra-molecular O-H⋯O hydrogen bond. In the crystal, weak C-H⋯F hydrogen bonds link mol-ecules into layers parallel to the ab plane.

Related literature

Marbofloxacin is a third-generation fluoro­quinolone for veterinary use, the anti­microbial activity of which depends upon its inhibition of DNA-gyrase and topoisomerase IV (Paradis et al., 2001 ▶; Thomas et al., 2001 ▶; Voermans et al., 2006 ▶). With a broad spectrum bactericidal activity and good efficacy, marbofloxacin is indicated for dermatological, respiratory and urinary tract infections resulting from both Gram-positive and Gram-negative bacteria (Lefebvre et al., 1998 ▶) and Mycoplasma (Spreng et al., 1995 ▶; Dossin et al., 1998 ▶; Carlotti et al., 1999 ▶; Ishak et al., 2008 ▶).

Experimental

Crystal data

C17H19FN4O4

M = 362.36

Triclinic,

a = 8.0145 (5) Å

b = 8.9218 (6) Å

c = 13.0874 (8) Å

α = 91.65 (3)°

β = 99.65 (3)°

γ = 115.091 (10)°

V = 830.26 (16) Å3

Z = 2

Mo Kα radiation

μ = 0.11 mm−1

T = 296 K

0.31 × 0.13 × 0.03 mm

Data collection

Rigaku RAXIS-RAPID/ZJUG diffractometer

Absorption correction: multi-scan (Higashi, 1995 ▶) T min = 0.956, T max = 0.997

6601 measured reflections

2925 independent reflections

1428 reflections with I > 2σ(I)

R int = 0.052

Refinement

R[F 2 > 2σ(F 2)] = 0.055

wR(F 2) = 0.203

S = 1.00

2925 reflections

241 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.29 e Å−3

Δρmin = −0.34 e Å−3

Data collection: PROCESS-AUTO (Rigaku, 2006 ▶); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku, 2007 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812009312/nr2019sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812009312/nr2019Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812009312/nr2019Isup3.cml

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

C17H19FN4O4	Z = 2
Mr = 362.36	F(000) = 380
Triclinic, P1	Dx = 1.449 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.0145 (5) Å	Cell parameters from 4017 reflections
b = 8.9218 (6) Å	θ = 3.1–27.4°
c = 13.0874 (8) Å	µ = 0.11 mm−1
α = 91.65 (3)°	T = 296 K
β = 99.65 (3)°	Plates, yellow
γ = 115.091 (10)°	0.31 × 0.13 × 0.03 mm
V = 830.26 (16) Å3

Rigaku RAXIS-RAPID/ZJUG diffractometer	2925 independent reflections
Radiation source: rolling anode	1428 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.052
Detector resolution: 10.00 pixels mm-1	θmax = 25.0°, θmin = 3.1°
ω scans	h = −9→9
Absorption correction: multi-scan (Higashi, 1995)	k = −10→10
Tmin = 0.956, Tmax = 0.997	l = −15→15
6601 measured reflections

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)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.203	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ2(Fo2) + (0.072P)2 + 0.8525P] where P = (Fo2 + 2Fc2)/3
2925 reflections	(Δ/σ)max < 0.001
241 parameters	Δρmax = 0.29 e Å−3
1 restraint	Δρmin = −0.34 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
F1	0.2105 (3)	0.1945 (3)	0.64667 (19)	0.0642 (7)
O1	0.2871 (5)	0.7762 (4)	1.0967 (2)	0.0680 (9)
H1	0.230 (6)	0.693 (4)	1.053 (3)	0.09 (2)*
O2	0.5831 (5)	0.9686 (4)	1.1352 (2)	0.0732 (10)
O3	0.1921 (4)	0.5352 (4)	0.9550 (2)	0.0594 (8)
O4	0.8358 (3)	0.6152 (3)	0.7475 (2)	0.0539 (8)
N1	0.9081 (4)	0.8423 (4)	0.8761 (3)	0.0499 (9)
N2	0.7233 (4)	0.7572 (4)	0.8983 (2)	0.0455 (8)
N3	0.5854 (4)	0.3404 (4)	0.6136 (2)	0.0494 (9)
N4	0.7031 (5)	0.1924 (4)	0.4634 (3)	0.0551 (9)
C1	0.4644 (7)	0.8439 (6)	1.0818 (3)	0.0576 (11)
C2	0.5010 (5)	0.7549 (5)	0.9964 (3)	0.0451 (10)
C3	0.3568 (6)	0.6070 (5)	0.9367 (3)	0.0467 (10)
C4	0.4097 (5)	0.5369 (4)	0.8514 (3)	0.0414 (9)
C5	0.2802 (5)	0.3970 (5)	0.7853 (3)	0.0475 (10)
H5	0.1554	0.3464	0.7926	0.057*
C6	0.3386 (5)	0.3344 (5)	0.7091 (3)	0.0484 (10)
C7	0.5238 (5)	0.4014 (4)	0.6918 (3)	0.0436 (9)
C8	0.6516 (5)	0.5420 (5)	0.7594 (3)	0.0441 (9)
C9	0.9600 (5)	0.7160 (5)	0.8421 (3)	0.0557 (11)
H9A	0.9574	0.6446	0.8969	0.067*
H9B	1.0876	0.7688	0.8302	0.067*
C10	0.6778 (5)	0.8265 (5)	0.9749 (3)	0.0463 (10)
H10	0.7678	0.9247	1.0140	0.056*
C11	0.5951 (5)	0.6118 (4)	0.8364 (3)	0.0400 (9)
C12	0.9089 (7)	0.9603 (5)	0.7983 (4)	0.0665 (13)
H12A	0.8252	0.8996	0.7343	0.100*
H12B	1.0339	1.0196	0.7856	0.100*
H12C	0.8681	1.0380	0.8246	0.100*
C13	0.4605 (6)	0.2587 (6)	0.5132 (3)	0.0628 (12)
H13A	0.3799	0.3129	0.4920	0.075*
H13B	0.3817	0.1428	0.5190	0.075*
C14	0.5809 (7)	0.2709 (6)	0.4340 (3)	0.0684 (13)
H14A	0.5007	0.2181	0.3667	0.082*
H14B	0.6560	0.3872	0.4272	0.082*
C15	0.8245 (6)	0.2699 (6)	0.5640 (3)	0.0651 (13)
H15A	0.9056	0.3855	0.5587	0.078*
H15B	0.9034	0.2138	0.5841	0.078*
C16	0.7106 (6)	0.2613 (5)	0.6461 (3)	0.0546 (11)
H16A	0.6367	0.1459	0.6557	0.065*
H16B	0.7939	0.3180	0.7120	0.065*
C17	0.8116 (7)	0.1965 (6)	0.3831 (4)	0.0840 (17)
H17A	0.7272	0.1399	0.3185	0.126*
H17B	0.8906	0.1422	0.4042	0.126*
H17C	0.8881	0.3101	0.3740	0.126*

	U11	U22	U33	U12	U13	U23
F1	0.0504 (14)	0.0478 (13)	0.0771 (17)	0.0064 (11)	0.0123 (12)	−0.0136 (12)
O1	0.077 (2)	0.081 (2)	0.0573 (19)	0.0394 (19)	0.0278 (17)	0.0012 (18)
O2	0.084 (2)	0.072 (2)	0.0611 (19)	0.0311 (18)	0.0186 (17)	−0.0087 (17)
O3	0.0514 (17)	0.0659 (18)	0.0658 (19)	0.0245 (15)	0.0267 (15)	0.0086 (15)
O4	0.0438 (15)	0.0543 (16)	0.0548 (17)	0.0115 (13)	0.0164 (13)	−0.0057 (13)
N1	0.0444 (19)	0.0450 (18)	0.056 (2)	0.0129 (15)	0.0172 (16)	0.0015 (16)
N2	0.0415 (18)	0.0460 (18)	0.0441 (18)	0.0137 (15)	0.0112 (14)	0.0023 (15)
N3	0.053 (2)	0.060 (2)	0.0391 (17)	0.0302 (17)	0.0041 (15)	−0.0071 (15)
N4	0.067 (2)	0.0451 (19)	0.052 (2)	0.0196 (17)	0.0221 (17)	−0.0016 (16)
C1	0.066 (3)	0.068 (3)	0.051 (3)	0.038 (2)	0.020 (2)	0.010 (2)
C2	0.059 (3)	0.048 (2)	0.036 (2)	0.029 (2)	0.0121 (18)	0.0061 (17)
C3	0.051 (2)	0.053 (2)	0.044 (2)	0.0278 (19)	0.0146 (19)	0.0114 (19)
C4	0.049 (2)	0.0373 (19)	0.040 (2)	0.0200 (17)	0.0092 (17)	0.0053 (16)
C5	0.042 (2)	0.045 (2)	0.055 (2)	0.0169 (18)	0.0115 (18)	0.0051 (19)
C6	0.042 (2)	0.038 (2)	0.056 (2)	0.0102 (17)	0.0063 (18)	−0.0031 (18)
C7	0.051 (2)	0.0363 (19)	0.046 (2)	0.0205 (17)	0.0110 (18)	0.0056 (17)
C8	0.042 (2)	0.046 (2)	0.044 (2)	0.0186 (17)	0.0121 (17)	0.0003 (18)
C9	0.042 (2)	0.057 (2)	0.059 (3)	0.0149 (19)	0.0090 (19)	−0.007 (2)
C10	0.054 (2)	0.048 (2)	0.038 (2)	0.0236 (19)	0.0104 (18)	−0.0031 (17)
C11	0.041 (2)	0.0352 (18)	0.0396 (19)	0.0131 (16)	0.0082 (16)	0.0025 (16)
C12	0.069 (3)	0.058 (3)	0.068 (3)	0.018 (2)	0.025 (2)	0.010 (2)
C13	0.066 (3)	0.068 (3)	0.052 (3)	0.031 (2)	0.001 (2)	−0.010 (2)
C14	0.083 (3)	0.070 (3)	0.049 (3)	0.032 (3)	0.010 (2)	−0.001 (2)
C15	0.063 (3)	0.079 (3)	0.057 (3)	0.034 (2)	0.015 (2)	−0.005 (2)
C16	0.063 (3)	0.061 (3)	0.053 (2)	0.038 (2)	0.015 (2)	0.005 (2)
C17	0.098 (4)	0.073 (3)	0.074 (3)	0.021 (3)	0.048 (3)	−0.007 (3)

F1—C6	1.361 (4)	C5—C6	1.368 (5)
O1—C1	1.339 (5)	C5—H5	0.9300
O1—H1	0.83 (3)	C6—C7	1.407 (5)
O2—C1	1.210 (5)	C7—C8	1.395 (5)
O3—C3	1.267 (4)	C8—C11	1.401 (5)
O4—C8	1.377 (4)	C9—H9A	0.9700
O4—C9	1.448 (4)	C9—H9B	0.9700
N1—N2	1.434 (4)	C10—H10	0.9300
N1—C9	1.439 (5)	C12—H12A	0.9600
N1—C12	1.484 (6)	C12—H12B	0.9600
N2—C10	1.341 (4)	C12—H12C	0.9600
N2—C11	1.387 (4)	C13—C14	1.507 (6)
N3—C7	1.397 (4)	C13—H13A	0.9700
N3—C13	1.465 (5)	C13—H13B	0.9700
N3—C16	1.470 (5)	C14—H14A	0.9700
N4—C14	1.438 (6)	C14—H14B	0.9700
N4—C15	1.451 (5)	C15—C16	1.506 (5)
N4—C17	1.464 (5)	C15—H15A	0.9700
C1—C2	1.491 (5)	C15—H15B	0.9700
C2—C10	1.368 (5)	C16—H16A	0.9700
C2—C3	1.425 (5)	C16—H16B	0.9700
C3—C4	1.470 (5)	C17—H17A	0.9600
C4—C5	1.387 (5)	C17—H17B	0.9600
C4—C11	1.399 (5)	C17—H17C	0.9600
C1—O1—H1	106 (4)	H9A—C9—H9B	107.9
C8—O4—C9	111.3 (3)	N2—C10—C2	121.0 (3)
N2—N1—C9	106.7 (3)	N2—C10—H10	119.5
N2—N1—C12	109.9 (3)	C2—C10—H10	119.5
C9—N1—C12	113.8 (3)	N2—C11—C4	119.3 (3)
C10—N2—C11	122.3 (3)	N2—C11—C8	120.0 (3)
C10—N2—N1	118.4 (3)	C4—C11—C8	120.7 (3)
C11—N2—N1	119.1 (3)	N1—C12—H12A	109.5
C7—N3—C13	121.3 (3)	N1—C12—H12B	109.5
C7—N3—C16	117.4 (3)	H12A—C12—H12B	109.5
C13—N3—C16	110.8 (3)	N1—C12—H12C	109.5
C14—N4—C15	110.1 (3)	H12A—C12—H12C	109.5
C14—N4—C17	111.2 (4)	H12B—C12—H12C	109.5
C15—N4—C17	111.6 (4)	N3—C13—C14	108.0 (4)
O2—C1—O1	120.9 (4)	N3—C13—H13A	110.1
O2—C1—C2	123.9 (4)	C14—C13—H13A	110.1
O1—C1—C2	115.2 (4)	N3—C13—H13B	110.1
C10—C2—C3	121.6 (3)	C14—C13—H13B	110.1
C10—C2—C1	116.6 (3)	H13A—C13—H13B	108.4
C3—C2—C1	121.7 (4)	N4—C14—C13	111.6 (4)
O3—C3—C2	123.6 (3)	N4—C14—H14A	109.3
O3—C3—C4	120.3 (3)	C13—C14—H14A	109.3
C2—C3—C4	116.0 (3)	N4—C14—H14B	109.3
C5—C4—C11	118.8 (3)	C13—C14—H14B	109.3
C5—C4—C3	121.6 (4)	H14A—C14—H14B	108.0
C11—C4—C3	119.6 (3)	N4—C15—C16	111.0 (4)
C6—C5—C4	119.0 (4)	N4—C15—H15A	109.4
C6—C5—H5	120.5	C16—C15—H15A	109.4
C4—C5—H5	120.5	N4—C15—H15B	109.4
F1—C6—C5	118.2 (3)	C16—C15—H15B	109.4
F1—C6—C7	117.0 (3)	H15A—C15—H15B	108.0
C5—C6—C7	124.8 (3)	N3—C16—C15	109.4 (4)
N3—C7—C8	119.3 (3)	N3—C16—H16A	109.8
N3—C7—C6	125.6 (3)	C15—C16—H16A	109.8
C8—C7—C6	115.1 (3)	N3—C16—H16B	109.8
O4—C8—C7	118.6 (3)	C15—C16—H16B	109.8
O4—C8—C11	119.9 (3)	H16A—C16—H16B	108.2
C7—C8—C11	121.5 (3)	N4—C17—H17A	109.5
N1—C9—O4	112.4 (3)	N4—C17—H17B	109.5
N1—C9—H9A	109.1	H17A—C17—H17B	109.5
O4—C9—H9A	109.1	N4—C17—H17C	109.5
N1—C9—H9B	109.1	H17A—C17—H17C	109.5
O4—C9—H9B	109.1	H17B—C17—H17C	109.5
C9—N1—N2—C10	147.4 (4)	N3—C7—C8—C11	177.4 (4)
C12—N1—N2—C10	−88.8 (4)	C6—C7—C8—C11	−1.6 (6)
C9—N1—N2—C11	−36.1 (5)	N2—N1—C9—O4	62.1 (4)
C12—N1—N2—C11	87.7 (4)	C12—N1—C9—O4	−59.3 (4)
O2—C1—C2—C10	−3.8 (7)	C8—O4—C9—N1	−56.7 (4)
O1—C1—C2—C10	176.1 (4)	C11—N2—C10—C2	0.7 (6)
O2—C1—C2—C3	179.1 (4)	N1—N2—C10—C2	177.0 (4)
O1—C1—C2—C3	−1.0 (6)	C3—C2—C10—N2	−1.8 (6)
C10—C2—C3—O3	178.9 (4)	C1—C2—C10—N2	−178.9 (4)
C1—C2—C3—O3	−4.2 (6)	C10—N2—C11—C4	2.2 (6)
C10—C2—C3—C4	0.0 (6)	N1—N2—C11—C4	−174.1 (3)
C1—C2—C3—C4	177.0 (4)	C10—N2—C11—C8	−178.1 (4)
O3—C3—C4—C5	3.6 (6)	N1—N2—C11—C8	5.6 (5)
C2—C3—C4—C5	−177.5 (4)	C5—C4—C11—N2	176.4 (4)
O3—C3—C4—C11	−176.1 (4)	C3—C4—C11—N2	−3.9 (6)
C2—C3—C4—C11	2.8 (5)	C5—C4—C11—C8	−3.3 (6)
C11—C4—C5—C6	1.5 (6)	C3—C4—C11—C8	176.4 (4)
C3—C4—C5—C6	−178.2 (4)	O4—C8—C11—N2	2.0 (6)
C4—C5—C6—F1	178.3 (4)	C7—C8—C11—N2	−176.2 (4)
C4—C5—C6—C7	0.2 (7)	O4—C8—C11—C4	−178.3 (3)
C13—N3—C7—C8	−148.1 (4)	C7—C8—C11—C4	3.4 (6)
C16—N3—C7—C8	70.4 (5)	C7—N3—C13—C14	157.3 (4)
C13—N3—C7—C6	30.9 (6)	C16—N3—C13—C14	−58.9 (5)
C16—N3—C7—C6	−110.7 (5)	C15—N4—C14—C13	−59.0 (5)
F1—C6—C7—N3	2.7 (6)	C17—N4—C14—C13	176.7 (3)
C5—C6—C7—N3	−179.2 (4)	N3—C13—C14—N4	59.4 (5)
F1—C6—C7—C8	−178.3 (3)	C14—N4—C15—C16	57.3 (5)
C5—C6—C7—C8	−0.2 (6)	C17—N4—C15—C16	−178.7 (4)
C9—O4—C8—C7	−159.0 (4)	C7—N3—C16—C15	−156.2 (3)
C9—O4—C8—C11	22.7 (5)	C13—N3—C16—C15	58.4 (5)
N3—C7—C8—O4	−0.8 (6)	N4—C15—C16—N3	−56.9 (5)
C6—C7—C8—O4	−179.9 (4)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O3	0.83 (3)	1.77 (2)	2.560 (4)	159 (5)
C12—H12B···F1i	0.96	2.62	3.422 (3)	140 (4)
C15—H15B···F1ii	0.97	2.54	3.446 (3)	155 (5)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O3	0.83 (3)	1.77 (2)	2.560 (4)	159 (5)
C12—H12B⋯F1i	0.96	2.62	3.422 (3)	140 (4)
C15—H15B⋯F1ii	0.97	2.54	3.446 (3)	155 (5)

Symmetry codes: (i) ; (ii) .