Ethyl 7-chloro-1-cyclo-propyl-6-fluoro-8-nitro-4-oxo-1,4-dihydro-quinoline-3-carboxyl-ate.

In the title compound, C(15)H(12)ClFN(2)O(5), mol-ecules are packed in the crystal lattice in a parallel fashion sustained by various C-H⋯O [C⋯O = 3.065 (5)-3.537 (5) Å] and C-H⋯Cl [3.431 (5)-3.735 (4) Å] inter-actions.

Related literature

For the biological activities of fluoro­quinolone derivatives, see: Li et al. (2000 ▶); Mitscher (2005 ▶). For the synthesis of the title compound, see: Al-Qawasmeh et al. (2009 ▶); Al-Hiari et al. (2006 ▶).

Experimental

Crystal data

C15H12ClFN2O5

M = 354.72

Triclinic,

a = 8.2339 (16) Å

b = 9.1523 (18) Å

c = 10.736 (2) Å

α = 85.60 (3)°

β = 81.20 (3)°

γ = 74.13 (3)°

V = 768.5 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.29 mm−1

T = 291 K

0.96 × 0.35 × 0.21 mm

Data collection

Oxford Diffraction Xcalibur Eos diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009 ▶) T min = 0.857, T max = 1.000

4468 measured reflections

2713 independent reflections

1617 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.060

wR(F 2) = 0.195

S = 1.05

2713 reflections

218 parameters

H-atom parameters constrained

Δρmax = 0.29 e Å−3

Δρmin = −0.26 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: OLEX2 (Dolomanov et al., 2009 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812011373/ds2180sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812011373/ds2180Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812011373/ds2180Isup3.cml

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

C15H12ClFN2O5	F(000) = 364
Mr = 354.72	none
Triclinic, P1	Dx = 1.533 Mg m−3
Hall symbol: -P 1	Melting point: 438 K
a = 8.2339 (16) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.1523 (18) Å	Cell parameters from 1074 reflections
c = 10.736 (2) Å	θ = 3.1–29.0°
α = 85.60 (3)°	µ = 0.29 mm−1
β = 81.20 (3)°	T = 291 K
γ = 74.13 (3)°	Needle, yellow
V = 768.5 (3) Å3	0.96 × 0.35 × 0.21 mm
Z = 2

Oxford Diffraction Xcalibur Eos diffractometer	2713 independent reflections
Radiation source: Enhance (Mo) X-ray Source	1617 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.031
Detector resolution: 16.0534 pixels mm-1	θmax = 25.0°, θmin = 3.1°
ω scans	h = −8→9
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	k = −8→10
Tmin = 0.857, Tmax = 1.000	l = −12→10
4468 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.060	H-atom parameters constrained
wR(F2) = 0.195	w = 1/[σ2(Fo2) + (0.0824P)2 + 0.0377P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max < 0.001
2713 reflections	Δρmax = 0.29 e Å−3
218 parameters	Δρmin = −0.26 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.013 (5)

Experimental. CrysAlisPro, Agilent Technologies, Version 1.171.35.11 Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. (CrysAlisPro; Oxford Diffraction, 2009)

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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. The H atom was located from difference Fourier syntheses and its position and isotropic displacement parameter refined freely.

	x	y	z	Uiso*/Ueq
Cl1	0.12355 (14)	0.02366 (11)	0.15569 (10)	0.0800 (4)
N2	0.4807 (4)	−0.2165 (3)	−0.2558 (3)	0.0577 (8)
F1	0.1920 (3)	0.2933 (2)	0.0257 (2)	0.0921 (8)
N1	0.2887 (5)	−0.2409 (3)	0.0032 (3)	0.0651 (8)
O1	0.5691 (4)	0.1923 (3)	−0.3780 (3)	0.0833 (9)
C1	0.3081 (4)	−0.0978 (3)	−0.0616 (3)	0.0571 (9)
O3	0.1470 (4)	−0.2615 (3)	0.0265 (3)	0.0833 (9)
C3	0.2613 (5)	0.1687 (4)	−0.0426 (4)	0.0663 (10)
O5	0.8693 (4)	−0.2246 (3)	−0.5300 (3)	0.0892 (10)
O4	0.8073 (4)	0.0240 (3)	−0.5725 (3)	0.0872 (9)
C7	0.5977 (5)	−0.2042 (4)	−0.3557 (3)	0.0616 (10)
H7A	0.6527	−0.2921	−0.3992	0.074*
O2	0.4183 (4)	−0.3294 (3)	0.0328 (3)	0.0830 (9)
C2	0.2348 (4)	0.0321 (4)	0.0076 (3)	0.0611 (9)
C5	0.4362 (4)	0.0483 (4)	−0.2238 (3)	0.0572 (9)
C9	0.5534 (5)	0.0667 (4)	−0.3412 (4)	0.0607 (9)
C6	0.4075 (4)	−0.0917 (3)	−0.1800 (3)	0.0544 (9)
C8	0.6428 (5)	−0.0756 (4)	−0.3988 (3)	0.0615 (10)
C10	0.7786 (5)	−0.0812 (4)	−0.5092 (4)	0.0673 (10)
C15	0.4290 (5)	−0.3592 (4)	−0.2387 (4)	0.0669 (11)
H15A	0.4878	−0.4359	−0.1803	0.080*
C4	0.3601 (5)	0.1772 (4)	−0.1551 (4)	0.0668 (11)
H4A	0.3768	0.2704	−0.1862	0.080*
C14	0.3847 (5)	−0.4180 (4)	−0.3509 (4)	0.0797 (13)
H14A	0.4181	−0.5271	−0.3605	0.096*
H14B	0.3885	−0.3580	−0.4292	0.096*
C13	0.2480 (5)	−0.3550 (4)	−0.2451 (4)	0.0774 (12)
H13A	0.1693	−0.2570	−0.2595	0.093*
H13B	0.1989	−0.4262	−0.1907	0.093*
C11	1.0073 (6)	−0.2448 (5)	−0.6353 (5)	0.1002 (16)
H11A	0.9628	−0.2012	−0.7124	0.120*
H11B	1.0908	−0.1937	−0.6197	0.120*
C12	1.0855 (8)	−0.4041 (6)	−0.6479 (6)	0.146 (3)
H12A	1.1749	−0.4193	−0.7182	0.219*
H12B	1.0016	−0.4540	−0.6617	0.219*
H12C	1.1322	−0.4457	−0.5722	0.219*

	U11	U22	U33	U12	U13	U23
Cl1	0.0797 (8)	0.0847 (8)	0.0611 (7)	−0.0052 (6)	0.0105 (5)	−0.0156 (5)
N2	0.0693 (19)	0.0411 (14)	0.0518 (19)	−0.0083 (13)	0.0134 (15)	−0.0013 (12)
F1	0.0937 (18)	0.0661 (13)	0.104 (2)	−0.0100 (12)	0.0191 (15)	−0.0361 (12)
N1	0.075 (2)	0.0571 (18)	0.053 (2)	−0.0090 (17)	0.0059 (17)	−0.0042 (14)
O1	0.107 (2)	0.0508 (14)	0.083 (2)	−0.0210 (14)	0.0142 (17)	0.0036 (13)
C1	0.057 (2)	0.0463 (18)	0.061 (2)	−0.0079 (16)	0.0012 (18)	−0.0004 (16)
O3	0.080 (2)	0.0817 (18)	0.079 (2)	−0.0246 (16)	0.0223 (16)	−0.0017 (15)
C3	0.071 (2)	0.0511 (19)	0.071 (3)	−0.0066 (18)	0.001 (2)	−0.0195 (18)
O5	0.084 (2)	0.0671 (16)	0.091 (2)	−0.0053 (15)	0.0381 (17)	−0.0004 (15)
O4	0.089 (2)	0.0769 (17)	0.084 (2)	−0.0202 (16)	0.0145 (17)	0.0147 (15)
C7	0.066 (2)	0.0482 (18)	0.056 (2)	−0.0011 (17)	0.0079 (19)	0.0019 (16)
O2	0.093 (2)	0.0639 (15)	0.080 (2)	−0.0013 (15)	−0.0148 (17)	0.0056 (14)
C2	0.054 (2)	0.063 (2)	0.057 (2)	−0.0038 (17)	0.0024 (18)	−0.0075 (17)
C5	0.061 (2)	0.0502 (18)	0.055 (2)	−0.0107 (16)	0.0004 (18)	−0.0015 (16)
C9	0.066 (2)	0.0518 (19)	0.059 (2)	−0.0126 (17)	−0.0004 (19)	0.0021 (16)
C6	0.055 (2)	0.0463 (18)	0.054 (2)	−0.0047 (15)	0.0003 (17)	−0.0010 (15)
C8	0.064 (2)	0.056 (2)	0.057 (2)	−0.0111 (17)	0.0043 (19)	0.0020 (16)
C10	0.067 (2)	0.068 (2)	0.058 (3)	−0.012 (2)	0.0045 (19)	0.0027 (19)
C15	0.080 (3)	0.0407 (18)	0.063 (3)	−0.0031 (18)	0.017 (2)	0.0002 (16)
C4	0.074 (3)	0.0480 (19)	0.071 (3)	−0.0110 (18)	0.004 (2)	−0.0055 (17)
C14	0.109 (3)	0.0484 (19)	0.071 (3)	−0.021 (2)	0.027 (2)	−0.0162 (18)
C13	0.081 (3)	0.057 (2)	0.084 (3)	−0.017 (2)	0.023 (2)	−0.0202 (19)
C11	0.081 (3)	0.094 (3)	0.096 (4)	−0.007 (3)	0.047 (3)	0.001 (3)
C12	0.147 (5)	0.108 (4)	0.131 (5)	0.004 (4)	0.075 (4)	−0.005 (4)

Cl1—C2	1.716 (4)	C5—C6	1.399 (4)
N2—C7	1.347 (4)	C5—C9	1.494 (5)
N2—C6	1.396 (4)	C9—C8	1.442 (5)
N2—C15	1.471 (4)	C8—C10	1.494 (5)
F1—C3	1.345 (4)	C15—C14	1.487 (5)
N1—O3	1.218 (4)	C15—C13	1.492 (5)
N1—O2	1.220 (4)	C15—H15A	0.9800
N1—C1	1.471 (4)	C4—H4A	0.9300
O1—C9	1.221 (4)	C14—C13	1.498 (5)
C1—C2	1.391 (5)	C14—H14A	0.9700
C1—C6	1.408 (5)	C14—H14B	0.9700
C3—C4	1.358 (5)	C13—H13A	0.9700
C3—C2	1.382 (5)	C13—H13B	0.9700
O5—C10	1.336 (5)	C11—C12	1.431 (7)
O5—C11	1.459 (5)	C11—H11A	0.9700
O4—C10	1.192 (4)	C11—H11B	0.9700
C7—C8	1.357 (4)	C12—H12A	0.9600
C7—H7A	0.9300	C12—H12B	0.9600
C5—C4	1.384 (5)	C12—H12C	0.9600
C7—N2—C6	118.9 (3)	N2—C15—C14	117.5 (3)
C7—N2—C15	117.2 (3)	N2—C15—C13	119.2 (3)
C6—N2—C15	123.7 (3)	C14—C15—C13	60.4 (3)
O3—N1—O2	124.7 (3)	N2—C15—H15A	116.1
O3—N1—C1	119.0 (3)	C14—C15—H15A	116.1
O2—N1—C1	116.3 (3)	C13—C15—H15A	116.1
C2—C1—C6	121.3 (3)	C3—C4—C5	120.6 (3)
C2—C1—N1	115.2 (3)	C3—C4—H4A	119.7
C6—C1—N1	123.2 (3)	C5—C4—H4A	119.7
F1—C3—C4	120.4 (3)	C15—C14—C13	60.0 (3)
F1—C3—C2	118.0 (3)	C15—C14—H14A	117.8
C4—C3—C2	121.6 (3)	C13—C14—H14A	117.8
C10—O5—C11	115.8 (3)	C15—C14—H14B	117.8
N2—C7—C8	126.1 (3)	C13—C14—H14B	117.8
N2—C7—H7A	116.9	H14A—C14—H14B	114.9
C8—C7—H7A	116.9	C15—C13—C14	59.7 (2)
C3—C2—C1	118.4 (3)	C15—C13—H13A	117.8
C3—C2—Cl1	120.0 (3)	C14—C13—H13A	117.8
C1—C2—Cl1	121.5 (3)	C15—C13—H13B	117.8
C4—C5—C6	120.2 (3)	C14—C13—H13B	117.8
C4—C5—C9	116.7 (3)	H13A—C13—H13B	114.9
C6—C5—C9	123.1 (3)	C12—C11—O5	108.5 (4)
O1—C9—C8	126.4 (3)	C12—C11—H11A	110.0
O1—C9—C5	120.5 (3)	O5—C11—H11A	110.0
C8—C9—C5	113.1 (3)	C12—C11—H11B	110.0
N2—C6—C5	117.9 (3)	O5—C11—H11B	110.0
N2—C6—C1	124.2 (3)	H11A—C11—H11B	108.4
C5—C6—C1	117.9 (3)	C11—C12—H12A	109.5
C7—C8—C9	119.6 (3)	C11—C12—H12B	109.5
C7—C8—C10	119.8 (3)	H12A—C12—H12B	109.5
C9—C8—C10	120.6 (3)	C11—C12—H12C	109.5
O4—C10—O5	122.6 (4)	H12A—C12—H12C	109.5
O4—C10—C8	126.8 (4)	H12B—C12—H12C	109.5
O5—C10—C8	110.6 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14A···O1i	0.97	2.54	3.489 (4)	167
C14—H14B···O1ii	0.97	2.51	3.471 (5)	172
C15—H15A···O2iii	0.98	2.58	3.537 (5)	165
C4—H4A···O2iv	0.93	2.71	3.065 (5)	104
C13—H13A···O4ii	0.97	2.71	3.439 (5)	132
C11—H11A···Cl1v	0.97	2.91	3.431 (5)	115
C13—H13A···Cl1vi	0.97	2.89	3.735 (4)	146

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C14—H14A⋯O1i	0.97	2.54	3.489 (4)	167
C14—H14B⋯O1ii	0.97	2.51	3.471 (5)	172
C15—H15A⋯O2iii	0.98	2.58	3.537 (5)	165
C4—H4A⋯O2iv	0.93	2.71	3.065 (5)	104
C13—H13A⋯O4ii	0.97	2.71	3.439 (5)	132
C11—H11A⋯Cl1v	0.97	2.91	3.431 (5)	115
C13—H13A⋯Cl1vi	0.97	2.89	3.735 (4)	146

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) ; (vi) .