4-Oxo-1,4-dihydro­benzo[h][1,3]thia­zeto[3,2-a]quinoline-1,3-dicarb­oxy­lic acid

Dawe, L.N.; Ahmed, A.; Daneshtalab, M.

doi:10.1107/S1600536811003333

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 2| February 2011| Page o529

doi:10.1107/S1600536811003333

Open

access

4-Oxo-1,4-dihydrobenzo[h][1,3]thiazeto[3,2-a]quinoline-1,3-dicarboxylic acid

Louise N. Dawe,^a Abeer Ahmed ^b and Mohsen Daneshtalab ^b ^*

^aDepartment of Chemistry, Memorial University of Newfoundland, St John's, NL, Canada A1B 3X7, and ^bSchool of Pharmacy, Memorial University of Newfoundland, St John's, NL, Canada A1B 3V6
^*Correspondence e-mail: mohsen@mun.ca

(Received 17 January 2011; accepted 25 January 2011; online 29 January 2011)

In the title molecule, C₁₆H₉NO₅S, there is an intramolecular O—H⋯O hydrogen bond involving the quinolone carbonyl O atom and a carboxyl OH group. In the crystal, intermolecular O—H⋯O hydrogen bonds between the carbonyl group of the quinolone carboxyl group, and a second carboxyl group on the thiazeto moiety lead to the formation of chains propagating along [201] and perpendicular to the π-stacks of molecules.

Related literature

For background to the biological importance of thiazetoquinoline antibiotics, see: Ozaki et al. (1991 ). For similar work using different procedures, see: Ito et al. (1992 , 1994 ); Matsuoka et al. (1999 ).

Experimental

Crystal data

C₁₆H₉NO₅S
M_r = 327.31
Monoclinic, P 2₁ /c
a = 7.237 (2) Å
b = 16.171 (5) Å
c = 11.929 (4) Å
β = 106.081 (8)°
V = 1341.5 (7) Å³
Z = 4
Mo Kα radiation
μ = 0.27 mm⁻¹
T = 153 K
0.18 × 0.04 × 0.04 mm

Data collection

Rigaku Saturn diffractometer
Absorption correction: numerical (ABSCOR; Higashi, 1999 ) T_min = 0.974, T_max = 0.996
17300 measured reflections
2769 independent reflections
2614 reflections with I > 2σ(I)
R_int = 0.074

Refinement

R[F² > 2σ(F²)] = 0.088
wR(F²) = 0.164
S = 1.30
2769 reflections
214 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.31 e Å⁻³
Δρ_min = −0.31 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O5—H5A⋯O1	0.96 (4)	1.57 (4)	2.504 (4)	161 (4)
O3—H3⋯O4ⁱ	0.97 (3)	1.62 (3)	2.569 (4)	166 (3)
Symmetry code: (i) $[x-1, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

Table 2
π⋯π interactions (Å, °)

Angle of elevation defined as the angle of the Cg(I)→Cg(J) vector and the normal to plane J. Cg1, Cg2 and Cg3 are the centroids of the C7–C12, N1/C1–C4/C13 and C4–C7/C12/C13 rings, respectively.

π⋯π	Distance	Angle of Elevation
Cg1⋯Cg2ⁱ	3.560 (2)	19.56
Cg3⋯Cg2ⁱ	3.644 (2)	22.75
Cg3⋯Cg3ⁱ	3.688 (2)	24.39
Symmetry code: (i) −x + 1, −y, −z.

Data collection: CrystalClear (Rigaku, 2005 ); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2006 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811003333/su2249sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811003333/su2249Isup2.hkl

checkCIF report

Comment top

4-oxo-1,4-dihydroquinoline-3-carboxylic acid derivatives (quinolones) are an important class of antibacterial agents, and a significant market exists for thiazetoquinoline antibiotics (Matsuoka et al.,1999; Ito et al., 1992; Ito et al., 1994; Ozaki et al., 1991). To this end, the title comound was obtained from the reaction of ethyl 2-{[2- ethoxy-2-oxoethyl)thio)-4-hydroxybenzo[h]quinoline-3-carboxylate with 1,2-dibromopropane in the presence of a catalytic amount of KI, followed by saponification using sodium hydroxide.

The molecular structure of the title molecule is shown in Fig. 1. It exhibits intra- (O5—H5a···O1) and intermolecular (O3—H3···O4ⁱ) hydrogen bonding (Table 1 and Fig. 2) leading to a chain-like arrangement of molecules which run along [201] and perpendicular to the π stacks (Fig. 2). Centroid-centroid distances range from 3.560 (2) to 3.688 (2) Å with angles of elevation between 19.56 and 24.39° (Table 2), while the inter-planar distance, as defined by the adjacent 14-atom (N1,C1—C13) ring system is 3.34 (1) Å.

Related literature top

For background to the biological importance of thiazetoquinoline antibiotics, see: Ozaki et al. (1991). For similar work using different procedures, see: Ito et al. (1992, 1994); Matsuoka et al. (1999).

Experimental top

To a mixture of ethyl 2-{[2- ethoxy-2-oxoethyl)thio)-4-hydroxybenzo[h]quinoline-3-carboxylate (1 mmol) and K₂CO₃ (2.8 mmol) in dry DMF (25 ml) under a nitrogen atmosphere was added 1,2-dibromopropane (2.8 mmol) along with a catlytic amount of KI. The reaction mixture was heated at 343 K for 24 h, and then poured into ice-H₂O. The resulting thiazetoquinoline derivative was collected by filtration. The separated product was reacted with sodium hydroxide (2.2 mmol) in water (20 ml) and heated at 373 K for 3–4 h. After being cooled, the reaction mixture was neutralized with hydrochloric acid (1 mol/L), extracted with CH₂Cl₂, dried over MgSO₄, and then evaporated. The obtained solid was purified by recrystallization from ethanol to afford the title compound as a yellowish white powder. Mp. 508 K, yield = 39%. ¹H-NMR and ¹³C-NMR data are given in the archived CIF.

Computing details top

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear (Rigaku, 2005); data reduction: CrystalClear (Rigaku, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2006); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

	Fig. 1. A view of the molecular structure of the title molecule, with displacement ellipsoids drawn at the 50% probability level.
	Fig. 2. A partial view of the crystal packing of the title compound. Both the hydrogen bonding [symmetry codes: (i) x-1, y, z; (ii) x, -y+1/2, z+1/2; (iii) x+1, y, z+1] and π···π interactions [symmetry codes: (ii) x, -y+1/2, z+1/2; (iv) -x+1, y+1/2, -z+1/2] are shown as dashed lines; ring centroids are marked by small spheres. See Tables 1 and 2 for details.

4-Oxo-1,4-dihydrobenzo[h][1,3]thiazeto[3,2-a]quinoline-1,3- dicarboxylic acid top

Crystal data top

C₁₆H₉NO₅S	F(000) = 672
M_r = 327.31	D_x = 1.621 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71075 Å
Hall symbol: -P 2ybc	Cell parameters from 4915 reflections
a = 7.237 (2) Å	θ = 2.2–30.6°
b = 16.171 (5) Å	µ = 0.27 mm⁻¹
c = 11.929 (4) Å	T = 153 K
β = 106.081 (8)°	Needle, colourless
V = 1341.5 (7) Å³	0.18 × 0.04 × 0.04 mm
Z = 4

Data collection top

Rigaku Saturn diffractometer	2769 independent reflections
Radiation source: fine-focus sealed tube	2614 reflections with I > 2σ(I)
Graphite - Rigaku SHINE monochromator	R_int = 0.074
Detector resolution: 14.63 pixels mm^-1	θ_max = 26.5°, θ_min = 2.5°
ω scans	h = −9→9
Absorption correction: numerical (ABSCOR; Higashi, 1999)	k = −20→20
T_min = 0.974, T_max = 0.996	l = −14→14
17300 measured reflections

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)] = 0.088	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.164	H atoms treated by a mixture of independent and constrained refinement
S = 1.30	w = 1/[σ²(F_o²) + (0.0366P)² + 2.1946P] where P = (F_o² + 2F_c²)/3
2769 reflections	(Δ/σ)_max < 0.001
214 parameters	Δρ_max = 0.31 e Å⁻³
2 restraints	Δρ_min = −0.31 e Å⁻³

Crystal data top

C₁₆H₉NO₅S	V = 1341.5 (7) Å³
M_r = 327.31	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 7.237 (2) Å	µ = 0.27 mm⁻¹
b = 16.171 (5) Å	T = 153 K
c = 11.929 (4) Å	0.18 × 0.04 × 0.04 mm
β = 106.081 (8)°

Data collection top

Rigaku Saturn diffractometer	2769 independent reflections
Absorption correction: numerical (ABSCOR; Higashi, 1999)	2614 reflections with I > 2σ(I)
T_min = 0.974, T_max = 0.996	R_int = 0.074
17300 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.088	2 restraints
wR(F²) = 0.164	H atoms treated by a mixture of independent and constrained refinement
S = 1.30	Δρ_max = 0.31 e Å⁻³
2769 reflections	Δρ_min = −0.31 e Å⁻³
214 parameters

Special details top

Experimental. Spectroscopic data:

¹H-NMR: (500 MHz, DMSO-d6): δ= 8.27(1H, d, J=8.8), 8.25(1H, d, J=8.4), 8.17(1H, d, J=7.5), 8.02(1H, d, J=8.80), 7.83(1H, dd, J=11.0, 4.0), 7.81–7.76(1H, m), 7.73(1H, s)}.

¹³C-NMR: (500 MHz, DMSO-d6): δ= 175.76, 165.64, 165.25, 164.26, 136.09, 135.26, 129.58, 128.97, 127.58, 126.05, 122.67, 122.33, 121.53, 121.15, 103.64, 70.43.

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
S1	0.60834 (14)	0.26465 (6)	0.14885 (8)	0.0347 (3)
O1	0.5029 (4)	−0.01520 (17)	0.3384 (2)	0.0387 (7)
O2	0.2537 (4)	0.33079 (19)	−0.0999 (3)	0.0512 (8)
O3	0.1270 (4)	0.25356 (17)	0.0178 (2)	0.0370 (6)
O4	0.7870 (4)	0.20609 (17)	0.3966 (2)	0.0379 (7)
O5	0.7226 (4)	0.08587 (19)	0.4695 (2)	0.0439 (7)
N1	0.4277 (4)	0.14703 (17)	0.0711 (2)	0.0257 (6)
C1	0.5397 (5)	0.1656 (2)	0.1790 (3)	0.0274 (7)
C2	0.5731 (5)	0.1139 (2)	0.2722 (3)	0.0289 (8)
C3	0.4829 (5)	0.0354 (2)	0.2544 (3)	0.0303 (8)
C4	0.3696 (5)	0.0139 (2)	0.1369 (3)	0.0277 (8)
C5	0.2892 (5)	−0.0668 (2)	0.1153 (3)	0.0318 (8)
H5	0.3105	−0.1057	0.1774	0.038*
C6	0.1828 (5)	−0.0887 (2)	0.0074 (3)	0.0317 (8)
H6	0.1297	−0.1428	−0.0048	0.038*
C7	0.1484 (5)	−0.0329 (2)	−0.0882 (3)	0.0281 (8)
C8	0.0343 (5)	−0.0566 (2)	−0.2002 (3)	0.0327 (8)
H8	−0.0180	−0.1108	−0.2118	0.039*
C9	−0.0019 (5)	−0.0027 (3)	−0.2920 (3)	0.0364 (9)
H9	−0.0819	−0.0190	−0.3661	0.044*
C10	0.0790 (6)	0.0762 (2)	−0.2765 (3)	0.0359 (9)
H10	0.0552	0.1130	−0.3410	0.043*
C11	0.1927 (5)	0.1015 (2)	−0.1696 (3)	0.0324 (8)
H11	0.2475	0.1553	−0.1611	0.039*
C12	0.2288 (5)	0.0480 (2)	−0.0719 (3)	0.0275 (8)
C13	0.3401 (5)	0.0702 (2)	0.0439 (3)	0.0254 (7)
C14	0.4427 (5)	0.2249 (2)	0.0104 (3)	0.0298 (8)
H14	0.5090	0.2174	−0.0521	0.036*
C15	0.2618 (5)	0.2759 (2)	−0.0304 (3)	0.0327 (8)
C16	0.7025 (5)	0.1379 (2)	0.3852 (3)	0.0332 (9)
H5A	0.649 (6)	0.039 (2)	0.432 (4)	0.052*
H3	0.008 (4)	0.277 (2)	−0.029 (3)	0.044*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0343 (5)	0.0303 (5)	0.0351 (5)	−0.0046 (4)	0.0023 (4)	−0.0016 (4)
O1	0.0403 (16)	0.0408 (16)	0.0313 (14)	0.0000 (12)	0.0036 (12)	0.0104 (12)
O2	0.0460 (17)	0.0450 (17)	0.062 (2)	0.0053 (14)	0.0138 (15)	0.0244 (16)
O3	0.0304 (14)	0.0391 (15)	0.0396 (15)	0.0034 (12)	0.0065 (12)	0.0059 (12)
O4	0.0335 (14)	0.0420 (16)	0.0337 (14)	−0.0013 (13)	0.0022 (11)	−0.0073 (12)
O5	0.0438 (17)	0.0558 (19)	0.0260 (14)	−0.0055 (14)	−0.0006 (12)	0.0038 (13)
N1	0.0257 (15)	0.0240 (15)	0.0263 (15)	−0.0017 (12)	0.0053 (12)	0.0024 (12)
C1	0.0220 (17)	0.0300 (18)	0.0289 (18)	−0.0005 (14)	0.0051 (14)	−0.0049 (15)
C2	0.0265 (18)	0.033 (2)	0.0273 (18)	−0.0005 (15)	0.0080 (14)	−0.0024 (15)
C3	0.0285 (18)	0.036 (2)	0.0268 (18)	0.0060 (16)	0.0076 (14)	0.0044 (15)
C4	0.0243 (17)	0.0300 (19)	0.0294 (18)	0.0035 (15)	0.0087 (14)	0.0009 (15)
C5	0.0285 (19)	0.0283 (19)	0.040 (2)	0.0039 (15)	0.0111 (16)	0.0066 (16)
C6	0.0278 (18)	0.0252 (19)	0.042 (2)	0.0007 (15)	0.0092 (16)	0.0008 (16)
C7	0.0237 (17)	0.0275 (18)	0.0326 (19)	0.0035 (14)	0.0072 (14)	−0.0029 (15)
C8	0.0259 (18)	0.033 (2)	0.039 (2)	−0.0002 (15)	0.0076 (16)	−0.0087 (17)
C9	0.0282 (19)	0.045 (2)	0.031 (2)	0.0022 (17)	0.0004 (15)	−0.0106 (17)
C10	0.039 (2)	0.038 (2)	0.0280 (19)	0.0004 (18)	0.0058 (16)	0.0025 (17)
C11	0.034 (2)	0.0300 (19)	0.0323 (19)	−0.0032 (16)	0.0082 (16)	−0.0041 (16)
C12	0.0220 (17)	0.0298 (19)	0.0303 (18)	0.0010 (14)	0.0065 (14)	−0.0007 (15)
C13	0.0224 (16)	0.0250 (17)	0.0302 (18)	0.0013 (14)	0.0094 (14)	0.0003 (15)
C14	0.0265 (18)	0.0290 (19)	0.0329 (19)	0.0002 (15)	0.0065 (15)	0.0027 (15)
C15	0.035 (2)	0.0271 (19)	0.0325 (19)	−0.0016 (16)	0.0029 (16)	−0.0013 (16)
C16	0.0300 (19)	0.044 (2)	0.0267 (19)	0.0051 (17)	0.0093 (15)	−0.0021 (17)

Geometric parameters (Å, º) top

S1—C1	1.744 (4)	C5—C6	1.351 (5)
S1—C14	1.866 (4)	C5—H5	0.9500
O1—C3	1.271 (4)	C6—C7	1.421 (5)
O2—C15	1.205 (4)	C6—H6	0.9500
O3—C15	1.314 (5)	C7—C8	1.416 (5)
O3—H3	0.963 (19)	C7—C12	1.423 (5)
O4—C16	1.250 (5)	C8—C9	1.366 (5)
O5—C16	1.288 (5)	C8—H8	0.9500
O5—H5A	0.965 (19)	C9—C10	1.394 (6)
N1—C1	1.350 (4)	C9—H9	0.9500
N1—C13	1.392 (4)	C10—C11	1.375 (5)
N1—C14	1.472 (4)	C10—H10	0.9500
C1—C2	1.358 (5)	C11—C12	1.416 (5)
C2—C3	1.416 (5)	C11—H11	0.9500
C2—C16	1.464 (5)	C12—C13	1.438 (5)
C3—C4	1.456 (5)	C14—C15	1.509 (5)
C4—C13	1.406 (5)	C14—H14	1.0000
C4—C5	1.423 (5)

C1—S1—C14	73.49 (16)	C7—C8—H8	119.5
C15—O3—H3	107 (3)	C8—C9—C10	119.8 (3)
C16—O5—H5A	103 (3)	C8—C9—H9	120.1
C1—N1—C13	122.3 (3)	C10—C9—H9	120.1
C1—N1—C14	99.9 (3)	C11—C10—C9	121.1 (4)
C13—N1—C14	137.7 (3)	C11—C10—H10	119.5
N1—C1—C2	124.6 (3)	C9—C10—H10	119.5
N1—C1—S1	97.9 (2)	C10—C11—C12	120.5 (3)
C2—C1—S1	137.5 (3)	C10—C11—H11	119.7
C1—C2—C3	117.2 (3)	C12—C11—H11	119.7
C1—C2—C16	121.0 (3)	C11—C12—C7	118.3 (3)
C3—C2—C16	121.8 (3)	C11—C12—C13	124.3 (3)
O1—C3—C2	120.8 (3)	C7—C12—C13	117.3 (3)
O1—C3—C4	121.0 (3)	N1—C13—C4	115.7 (3)
C2—C3—C4	118.2 (3)	N1—C13—C12	123.0 (3)
C13—C4—C5	119.1 (3)	C4—C13—C12	121.3 (3)
C13—C4—C3	121.8 (3)	N1—C14—C15	116.8 (3)
C5—C4—C3	119.1 (3)	N1—C14—S1	88.6 (2)
C6—C5—C4	120.6 (3)	C15—C14—S1	112.6 (3)
C6—C5—H5	119.7	N1—C14—H14	112.3
C4—C5—H5	119.7	C15—C14—H14	112.3
C5—C6—C7	121.7 (3)	S1—C14—H14	112.3
C5—C6—H6	119.2	O2—C15—O3	127.1 (4)
C7—C6—H6	119.2	O2—C15—C14	119.8 (4)
C8—C7—C6	120.8 (3)	O3—C15—C14	113.1 (3)
C8—C7—C12	119.2 (3)	O4—C16—O5	123.0 (3)
C6—C7—C12	120.0 (3)	O4—C16—C2	120.2 (3)
C9—C8—C7	121.0 (4)	O5—C16—C2	116.8 (4)
C9—C8—H8	119.5

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5A···O1	0.96 (4)	1.57 (4)	2.504 (4)	161 (4)
O3—H3···O4ⁱ	0.97 (3)	1.62 (3)	2.569 (4)	166 (3)

Symmetry code: (i) x−1, −y+1/2, z−1/2.

Experimental details

Crystal data
Chemical formula	C₁₆H₉NO₅S
M_r	327.31
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	153
a, b, c (Å)	7.237 (2), 16.171 (5), 11.929 (4)
β (°)	106.081 (8)
V (Å³)	1341.5 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.27
Crystal size (mm)	0.18 × 0.04 × 0.04

Data collection
Diffractometer	Rigaku Saturn diffractometer
Absorption correction	Numerical (ABSCOR; Higashi, 1999)
T_min, T_max	0.974, 0.996
No. of measured, independent and observed [I > 2σ(I)] reflections	17300, 2769, 2614
R_int	0.074
(sin θ/λ)_max (Å⁻¹)	0.628

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.088, 0.164, 1.30
No. of reflections	2769
No. of parameters	214
No. of restraints	2
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.31, −0.31

Computer programs: CrystalClear (Rigaku, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), Mercury (Macrae et al., 2006), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5A···O1	0.96 (4)	1.57 (4)	2.504 (4)	161 (4)
O3—H3···O4ⁱ	0.97 (3)	1.62 (3)	2.569 (4)	166 (3)

Symmetry code: (i) x−1, −y+1/2, z−1/2.

π···π interactions (Å, °) top

Angle of elevation defined as the angle of the Cg(I)→Cg(J) vector and the normal to plane J. Cg1, Cg2 and Cg3 are the centroids of the C7–C12, N1/C1–C4/C13 and C4–C7/C12/C13 rings, respectively.

π···π	Distance	Angle of Elevation
Cg1···Cg2ⁱ	3.560 (2)	19.56
Cg3···Cg2ⁱ	3.644 (2)	22.75
Cg3···Cg3ⁱ	3.688 (2)	24.39

Symmetry code: (i) -x+1, -y, -z.

References

Higashi, T. (1999). ABSCOR. Rigaku Corporation, Tokyo, Japan. Google Scholar
Ito, Y., Kato, H., Yasuda, S., Yoshida, T. & Yamamoto, Y. (1992). JP 92-21664 (July 27, 1992). Google Scholar
Ito, Y., Kato, H., Yasuda, S., Yoshida, T. & Yamamoto, Y. (1994). JP 06016677 A (Jan 25, 1994). Google Scholar
Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453–457. Web of Science CrossRef CAS IUCr Journals Google Scholar
Matsuoka, M., Segawa, J., Amimoto, I., Masui, Y., Tomii, Y., Kitano, M. & Kise, M. (1999). Chem. Pharm. Bull. (Tokyo), 47, 1765–1773. Web of Science CrossRef PubMed CAS Google Scholar
Ozaki, M., Matsuda, M., Tomii, Y., Kimura, K., Segawa, J., Kitano, M., Kise, M., Shibata, K., Otsuki, M. & Nishino, T. (1991). Antimicrob. Agents Chemother. 35, 2496–2499. CrossRef PubMed CAS Web of Science Google Scholar
Rigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 2| February 2011| Page o529

doi:10.1107/S1600536811003333

Open

access

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

4-Oxo-1,4-di­hydro­benzo[h][1,3]thia­zeto[3,2-a]quinoline-1,3-dicarb­­oxy­lic acid

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

References

organic compounds

4-Oxo-1,4-dihydrobenzo[h][1,3]thiazeto[3,2-a]quinoline-1,3-dicarboxylic acid