1-Cyclo­propyl-6-fluoro-7-(4-formyl­piperazin-1-yl)-4-oxo-1,4-dihydro­quinoline-3-carboxylic acid. Corrigendum

Li, X.-W.; Zhi, F.; Shen, J.-H.; Hu, Y.-Q.

doi:10.1107/S1600536805024426

addenda and errata

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 61| Part 9| September 2005| Page e3

https://doi.org/10.1107/S1600536805024426

1-Cyclopropyl-6-fluoro-7-(4-formylpiperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid. Corrigendum

Xian-Wen Li,^a,^b Feng Zhi,^b Jian-Hua Shen ^b and Yi-Qiao Hu ^b ^*

^aSchool of Life Sciences, Nanjing University, Nanjing 210093, People's Republic of China, and ^bDepartment of Biochemistry, Fujian Institute of Education, Fuzhou 350001, Fujian, People's Republic of China
^*Correspondence e-mail: hu_yiqiao@yahoo.com.cn

(Received 25 July 2005; accepted 29 July 2005; online 6 August 2005)

The crystal structure of the title compound, C₁₈H₁₈FN₃O₄, was published [Li et al. (2005 ). Acta Cryst. E61, o2235–o2236] with an error in the chemical formula and without location of the carboxyl H atom. This has now been corrected. The missing H atom was located and refined. This H atom is involved in an intramolecular O—H⋯O hydrogen bond with the carbonyl O atom.

1.

2. Experimental

2.1.1. Crystal data

C₁₈H₁₈FN₃O₄
M_r = 359.35
Triclinic, $[P \overline 1]$
a = 8.414 (2) Å
b = 9.513 (2) Å
c = 10.497 (2) Å
α = 102.57 (3)°
β = 96.58 (3)°
γ = 97.08 (3)°
V = 805.1 (3) Å³
Z = 2
D_x = 1.482 Mg m⁻³
Mo Kα radiation
Cell parameters from 25 reflections
θ = 9–13°
μ = 0.11 mm⁻¹
T = 293 (2) K
Block, yellow
0.48 × 0.21 × 0.19 mm

2.1.2. Data collection

Enraf–Nonius CAD-4 diffractometer
ω/2θ scans
Absorption correction: ψ scan(XCAD4; Harms & Wocadlo, 1995 )T_min = 0.947, T_max = 0.979
3379 measured reflections
3154 independent reflections
1822 reflections with I > 2σ(I)
R_int = 0.027
θ_max = 26.0°
h = 0 → 10
k = −11 → 11
l = −12 → 12
3 standard reflections every 200 reflections intensity decay: none

2.1.3. Refinement

Refinement on F²
R[F² > 2σ(F²)] = 0.050
wR(F²) = 0.140
S = 1.01
3154 reflections
238 parameters
H atoms treated by a mixture of independent and constrained refinement
w = 1/[σ²(F_o²) + (0.06P)² + 0.035P] where P = (F_o² + 2F_c²)/3
(Δ/σ)_max = 0.001
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3⋯O2	0.90 (1)	1.69 (2)	2.514 (3)	151 (3)

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536805024426/ci6625sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536805024426/ci6625Isup2.hkl

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); software used to prepare material for publication: SHELXL97.

1-Cyclopropyl-6-fluoro-7-(4-formylpiperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3- carboxylic acid top

Crystal data top

C₁₈H₁₈FN₃O₄	Z = 2
M_r = 359.35	F(000) = 376
Triclinic, P1	D_x = 1.482 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.414 (2) Å	Cell parameters from 25 reflections
b = 9.513 (2) Å	θ = 9–13°
c = 10.497 (2) Å	µ = 0.11 mm⁻¹
α = 102.57 (3)°	T = 293 K
β = 96.58 (3)°	Block, yellow
γ = 97.08 (3)°	0.48 × 0.21 × 0.19 mm
V = 805.1 (3) Å³

Data collection top

Enraf–Nonius CAD-4 diffractometer	1822 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.027
Graphite monochromator	θ_max = 26.0°, θ_min = 2.2°
ω/2θ scans	h = 0→10
Absorption correction: ψ scan (XCAD4; Harms & Wocadlo, 1995)	k = −11→11
T_min = 0.947, T_max = 0.979	l = −12→12
3379 measured reflections	3 standard reflections every 200 reflections
3154 independent reflections	intensity decay: none

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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.140	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ²(F_o²) + (0.06P)² + 0.035P] where P = (F_o² + 2F_c²)/3
3154 reflections	(Δ/σ)_max = 0.001
238 parameters	Δρ_max = 0.19 e Å⁻³
1 restraint	Δρ_min = −0.23 e Å⁻³

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
F1	0.52063 (18)	0.74819 (15)	−0.07309 (14)	0.0470 (4)
O1	0.7511 (3)	1.3189 (2)	0.4184 (2)	0.0826 (8)
O2	0.0708 (2)	0.32798 (18)	−0.24166 (17)	0.0451 (5)
O3	−0.1250 (3)	0.1022 (2)	−0.25234 (19)	0.0545 (5)
O4	−0.1734 (2)	0.0351 (2)	−0.06989 (19)	0.0544 (5)
N1	0.7420 (3)	1.0744 (2)	0.36587 (19)	0.0403 (5)
N2	0.5558 (2)	0.8162 (2)	0.20153 (19)	0.0362 (5)
N3	0.1515 (2)	0.38818 (19)	0.16083 (18)	0.0316 (5)
C1	0.7561 (4)	1.2033 (3)	0.4492 (3)	0.0548 (8)
H1A	0.7711	1.2056	0.5389	0.066*
C2	0.7396 (3)	0.9372 (3)	0.4054 (2)	0.0435 (7)
H2B	0.7486	0.9556	0.5008	0.052*
H2C	0.8322	0.8929	0.3790	0.052*
C3	0.5846 (3)	0.8319 (3)	0.3435 (2)	0.0440 (7)
H3A	0.5932	0.7375	0.3623	0.053*
H3B	0.4937	0.8678	0.3822	0.053*
C4	0.5543 (3)	0.9592 (3)	0.1686 (3)	0.0491 (7)
H4A	0.4662	1.0040	0.2039	0.059*
H4B	0.5366	0.9459	0.0735	0.059*
C5	0.7127 (3)	1.0574 (3)	0.2252 (2)	0.0458 (7)
H5A	0.8001	1.0157	0.1856	0.055*
H5B	0.7093	1.1519	0.2051	0.055*
C6	0.4412 (3)	0.6999 (2)	0.1267 (2)	0.0329 (6)
C7	0.4207 (3)	0.6684 (2)	−0.0128 (2)	0.0341 (6)
C8	0.3098 (3)	0.5589 (2)	−0.0912 (2)	0.0342 (6)
H8A	0.2966	0.5468	−0.1823	0.041*
C9	0.2149 (3)	0.4638 (2)	−0.0344 (2)	0.0318 (6)
C10	0.0981 (3)	0.3454 (2)	−0.1176 (2)	0.0335 (6)
C11	0.0169 (3)	0.2494 (2)	−0.0500 (2)	0.0343 (6)
C12	−0.1022 (3)	0.1194 (3)	−0.1222 (3)	0.0391 (6)
C13	0.0465 (3)	0.2758 (2)	0.0842 (2)	0.0340 (6)
H13A	−0.0094	0.2120	0.1251	0.041*
C14	0.2387 (3)	0.4863 (2)	0.1032 (2)	0.0298 (5)
C15	0.3470 (3)	0.6054 (2)	0.1819 (2)	0.0328 (6)
H15A	0.3561	0.6216	0.2732	0.039*
C16	0.1684 (3)	0.4125 (3)	0.3041 (2)	0.0364 (6)
H16A	0.1203	0.4948	0.3491	0.044*
C17	0.1618 (4)	0.2866 (3)	0.3656 (3)	0.0519 (8)
H17A	0.1490	0.1901	0.3079	0.062*
H17B	0.1088	0.2922	0.4435	0.062*
C18	0.3182 (3)	0.3848 (3)	0.3778 (3)	0.0487 (7)
H18A	0.3599	0.4500	0.4631	0.058*
H18B	0.4001	0.3479	0.3274	0.058*
H3	−0.066 (3)	0.174 (3)	−0.277 (3)	0.080*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
F1	0.0499 (10)	0.0444 (9)	0.0495 (9)	−0.0030 (7)	0.0129 (7)	0.0197 (7)
O1	0.110 (2)	0.0391 (12)	0.0880 (18)	0.0120 (13)	0.0026 (15)	−0.0020 (11)
O2	0.0506 (12)	0.0433 (10)	0.0369 (10)	0.0042 (9)	−0.0016 (9)	0.0053 (8)
O3	0.0563 (13)	0.0474 (12)	0.0469 (12)	−0.0068 (10)	−0.0070 (10)	−0.0012 (9)
O4	0.0480 (12)	0.0434 (11)	0.0616 (13)	−0.0125 (9)	−0.0044 (10)	0.0075 (10)
N1	0.0481 (14)	0.0320 (11)	0.0355 (12)	−0.0028 (10)	0.0015 (10)	0.0041 (9)
N2	0.0397 (13)	0.0290 (10)	0.0375 (12)	−0.0045 (9)	−0.0032 (9)	0.0128 (9)
N3	0.0324 (12)	0.0250 (10)	0.0346 (11)	−0.0003 (8)	0.0035 (9)	0.0046 (8)
C1	0.0558 (19)	0.0458 (17)	0.0520 (18)	−0.0011 (14)	0.0053 (15)	−0.0054 (14)
C2	0.0512 (17)	0.0388 (14)	0.0351 (14)	−0.0024 (13)	−0.0029 (12)	0.0074 (11)
C3	0.0490 (17)	0.0368 (14)	0.0435 (16)	−0.0042 (12)	0.0013 (13)	0.0127 (11)
C4	0.0552 (18)	0.0328 (14)	0.0544 (17)	−0.0023 (13)	−0.0128 (14)	0.0157 (12)
C5	0.0565 (18)	0.0326 (14)	0.0466 (16)	−0.0039 (13)	0.0041 (13)	0.0135 (12)
C6	0.0328 (14)	0.0262 (12)	0.0392 (14)	0.0052 (10)	0.0005 (11)	0.0085 (10)
C7	0.0351 (14)	0.0297 (12)	0.0403 (14)	0.0046 (11)	0.0058 (11)	0.0144 (11)
C8	0.0423 (15)	0.0316 (12)	0.0296 (13)	0.0092 (11)	0.0043 (11)	0.0074 (10)
C9	0.0334 (14)	0.0258 (12)	0.0359 (13)	0.0069 (10)	0.0030 (11)	0.0064 (10)
C10	0.0322 (14)	0.0293 (12)	0.0380 (15)	0.0095 (10)	0.0022 (11)	0.0049 (10)
C11	0.0296 (13)	0.0286 (12)	0.0412 (15)	0.0056 (10)	0.0005 (11)	0.0023 (11)
C12	0.0335 (15)	0.0319 (13)	0.0469 (16)	0.0051 (11)	−0.0017 (12)	0.0024 (11)
C13	0.0312 (14)	0.0258 (12)	0.0435 (15)	−0.0003 (10)	0.0040 (11)	0.0082 (10)
C14	0.0308 (13)	0.0233 (11)	0.0354 (13)	0.0056 (10)	0.0061 (10)	0.0057 (9)
C15	0.0370 (14)	0.0275 (12)	0.0330 (13)	0.0036 (10)	0.0039 (11)	0.0065 (10)
C16	0.0401 (15)	0.0322 (13)	0.0346 (13)	−0.0007 (11)	0.0058 (11)	0.0064 (10)
C17	0.0624 (19)	0.0425 (15)	0.0472 (16)	−0.0100 (14)	−0.0013 (14)	0.0176 (13)
C18	0.0450 (17)	0.0559 (17)	0.0414 (15)	0.0025 (14)	−0.0017 (13)	0.0102 (13)

Geometric parameters (Å, º) top

F1—C7	1.363 (3)	C5—H5A	0.97
O1—C1	1.216 (3)	C5—H5B	0.97
O2—C10	1.267 (3)	C6—C15	1.388 (3)
O3—C12	1.328 (3)	C6—C7	1.415 (3)
O3—H3	0.900 (10)	C7—C8	1.359 (3)
O4—C12	1.206 (3)	C8—C9	1.406 (3)
N1—C1	1.326 (3)	C8—H8A	0.93
N1—C5	1.439 (3)	C9—C14	1.400 (3)
N1—C2	1.452 (3)	C9—C10	1.449 (3)
N2—C6	1.398 (3)	C10—C11	1.429 (3)
N2—C3	1.454 (3)	C11—C13	1.363 (3)
N2—C4	1.475 (3)	C11—C12	1.490 (3)
N3—C13	1.341 (3)	C13—H13A	0.93
N3—C14	1.398 (3)	C14—C15	1.401 (3)
N3—C16	1.459 (3)	C15—H15A	0.93
C1—H1A	0.93	C16—C17	1.477 (3)
C2—C3	1.525 (3)	C16—C18	1.485 (4)
C2—H2B	0.97	C16—H16A	0.98
C2—H2C	0.97	C17—C18	1.492 (4)
C3—H3A	0.97	C17—H17A	0.97
C3—H3B	0.97	C17—H17B	0.97
C4—C5	1.508 (4)	C18—H18A	0.97
C4—H4A	0.97	C18—H18B	0.97
C4—H4B	0.97

C12—O3—H3	112 (2)	C7—C8—C9	119.9 (2)
C1—N1—C5	122.0 (2)	C7—C8—H8A	120.1
C1—N1—C2	124.3 (2)	C9—C8—H8A	120.1
C5—N1—C2	113.53 (19)	C14—C9—C8	118.1 (2)
C6—N2—C3	117.8 (2)	C14—C9—C10	121.8 (2)
C6—N2—C4	117.43 (19)	C8—C9—C10	120.2 (2)
C3—N2—C4	111.2 (2)	O2—C10—C11	122.5 (2)
C13—N3—C14	119.8 (2)	O2—C10—C9	122.2 (2)
C13—N3—C16	120.2 (2)	C11—C10—C9	115.4 (2)
C14—N3—C16	119.98 (18)	C13—C11—C10	120.2 (2)
O1—C1—N1	125.5 (3)	C13—C11—C12	118.1 (2)
O1—C1—H1A	117.2	C10—C11—C12	121.7 (2)
N1—C1—H1A	117.2	O4—C12—O3	121.4 (2)
N1—C2—C3	111.7 (2)	O4—C12—C11	124.3 (2)
N1—C2—H2B	109.3	O3—C12—C11	114.3 (2)
C3—C2—H2B	109.3	N3—C13—C11	124.1 (2)
N1—C2—H2C	109.3	N3—C13—H13A	118.0
C3—C2—H2C	109.3	C11—C13—H13A	118.0
H2B—C2—H2C	107.9	N3—C14—C9	118.8 (2)
N2—C3—C2	111.0 (2)	N3—C14—C15	120.5 (2)
N2—C3—H3A	109.4	C9—C14—C15	120.7 (2)
C2—C3—H3A	109.4	C6—C15—C14	121.6 (2)
N2—C3—H3B	109.4	C6—C15—H15A	119.2
C2—C3—H3B	109.4	C14—C15—H15A	119.2
H3A—C3—H3B	108.0	N3—C16—C17	119.7 (2)
N2—C4—C5	110.4 (2)	N3—C16—C18	119.6 (2)
N2—C4—H4A	109.6	C17—C16—C18	60.49 (18)
C5—C4—H4A	109.6	N3—C16—H16A	115.4
N2—C4—H4B	109.6	C17—C16—H16A	115.4
C5—C4—H4B	109.6	C18—C16—H16A	115.4
H4A—C4—H4B	108.1	C16—C17—C18	60.02 (17)
N1—C5—C4	109.9 (2)	C16—C17—H17A	117.8
N1—C5—H5A	109.7	C18—C17—H17A	117.8
C4—C5—H5A	109.7	C16—C17—H17B	117.8
N1—C5—H5B	109.7	C18—C17—H17B	117.8
C4—C5—H5B	109.7	H17A—C17—H17B	114.9
H5A—C5—H5B	108.2	C16—C18—C17	59.49 (17)
C15—C6—N2	123.4 (2)	C16—C18—H18A	117.8
C15—C6—C7	116.0 (2)	C17—C18—H18A	117.8
N2—C6—C7	120.6 (2)	C16—C18—H18B	117.8
C8—C7—F1	117.5 (2)	C17—C18—H18B	117.8
C8—C7—C6	123.6 (2)	H18A—C18—H18B	115.0
F1—C7—C6	118.9 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O2	0.90 (1)	1.69 (2)	2.514 (3)	151 (3)

References

Harms, K. & Wocadlo, S. (1995) XCAD4. University of Marburg, Germany. Google Scholar
Li, X.-W., Zhi, F., Shen, J.-H. & Hu, Y.-Q. (2005). Acta Cryst. E61, o2235–o2236. Web of Science CSD CrossRef IUCr Journals Google Scholar

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