X-ray diffraction study of the title compound, C11H11NO2, (I), has shown that the molecular geometry is similar to that of 1-ethyl-4-hydroxy-2-oxo-1,2-dihydroquinoline-3-carboxylic acid, (II) [Shishkina, Shishkin, Ukrainets, Dakkah & Sidorenko (2002). Acta Cryst. E58, o254-o256]. Observed elongations of the bonds around the N atom are caused by steric hindrance between the ethyl H atoms and the planar quinolone fragment. Exocyclic angles in the 4-position are also distorted, but, in contrast to (II), this distortion is caused by the formation of zigzag hydrogen-bonded chains along the [010] direction.
Supporting information
CCDC reference: 259590
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.003 Å
- R factor = 0.036
- wR factor = 0.103
- Data-to-parameter ratio = 8.9
checkCIF/PLATON results
No syntax errors found
Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
correct. If it is not, please give the correct count in the
_publ_section_exptl_refinement section of the submitted CIF.
From the CIF: _diffrn_reflns_theta_max 26.45
From the CIF: _reflns_number_total 1131
Count of symmetry unique reflns 1139
Completeness (_total/calc) 99.30%
TEST3: Check Friedels for noncentro structure
Estimate of Friedel pairs measured 0
Fraction of Friedel pairs measured 0.000
Are heavy atom types Z>Si present no
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
0 ALERT level C = Check and explain
1 ALERT level G = General alerts; check
0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
0 ALERT type 2 Indicator that the structure model may be wrong or deficient
0 ALERT type 3 Indicator that the structure quality may be low
1 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: P3 (Siemens,1989); cell refinement: P3; data reduction: XDISK and XPREP (Siemens, 1991); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP (Siemens, 1991); software used to prepare material for publication: WinGX (Farrugia, 1999).
Crystal data top
C11H11NO2 | F(000) = 400 |
Mr = 189.21 | Dx = 1.348 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 24 reflections |
a = 7.8474 (12) Å | θ = 11.0–12.0° |
b = 8.4660 (14) Å | µ = 0.09 mm−1 |
c = 14.033 (3) Å | T = 293 K |
V = 932.3 (3) Å3 | Polyhedron, colourless |
Z = 4 | 0.35 × 0.3 × 0.3 mm |
Data collection top
Siemens P3/PC diffractometer | θmax = 26.5°, θmin = 2.8° |
2θ/θ scans | h = 0→9 |
1226 measured reflections | k = 0→10 |
1131 independent reflections | l = 0→17 |
974 reflections with I > 2σ(I) | 2 standard reflections every 98 reflections |
Rint = 0.016 | intensity decay: 1% |
Refinement top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.036 | w = 1/[σ2(Fo2) + (0.0774P)2] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.103 | (Δ/σ)max < 0.001 |
S = 0.97 | Δρmax = 0.13 e Å−3 |
1131 reflections | Δρmin = −0.13 e Å−3 |
127 parameters | |
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O1 | 0.53866 (18) | 1.11314 (17) | 0.13981 (9) | 0.0505 (4) | |
O2 | 0.74016 (19) | 0.62483 (17) | 0.26303 (10) | 0.0541 (4) | |
H2 | 0.6473 | 0.6219 | 0.2898 | 0.065* | |
N1 | 0.79890 (18) | 1.02257 (18) | 0.09523 (10) | 0.0369 (4) | |
C2 | 0.6498 (2) | 1.0060 (2) | 0.14664 (13) | 0.0388 (4) | |
C3 | 0.6284 (2) | 0.8687 (2) | 0.20415 (13) | 0.0401 (4) | |
H3 | 0.5275 | 0.8556 | 0.2379 | 0.048* | |
C4 | 0.7513 (2) | 0.7569 (2) | 0.21091 (12) | 0.0376 (4) | |
C4A | 0.9112 (2) | 0.7775 (2) | 0.16043 (12) | 0.0339 (4) | |
C5 | 1.0444 (3) | 0.6677 (2) | 0.16819 (13) | 0.0416 (4) | |
H5 | 1.0304 | 0.5783 | 0.2059 | 0.05* | |
C6 | 1.1953 (3) | 0.6910 (3) | 0.12064 (14) | 0.0469 (5) | |
H6 | 1.2831 | 0.6179 | 0.1263 | 0.056* | |
C7 | 1.2161 (3) | 0.8242 (3) | 0.06404 (14) | 0.0467 (5) | |
H7 | 1.3183 | 0.8397 | 0.0318 | 0.056* | |
C8 | 1.0876 (2) | 0.9334 (2) | 0.05499 (14) | 0.0421 (5) | |
H8 | 1.1038 | 1.0219 | 0.0168 | 0.051* | |
C8A | 0.9317 (2) | 0.9127 (2) | 0.10297 (12) | 0.0341 (4) | |
C9 | 0.8166 (3) | 1.1655 (2) | 0.03641 (14) | 0.0423 (5) | |
H9A | 0.7058 | 1.1946 | 0.0113 | 0.051* | |
H9B | 0.8907 | 1.1426 | −0.0172 | 0.051* | |
C10 | 0.8888 (3) | 1.3028 (2) | 0.09170 (16) | 0.0495 (5) | |
H10A | 0.8996 | 1.3927 | 0.0504 | 0.074* | |
H10B | 0.9989 | 1.2749 | 0.1163 | 0.074* | |
H10C | 0.8139 | 1.3283 | 0.1436 | 0.074* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0455 (7) | 0.0487 (8) | 0.0572 (8) | 0.0119 (7) | 0.0070 (7) | 0.0034 (7) |
O2 | 0.0469 (8) | 0.0493 (8) | 0.0661 (8) | 0.0001 (7) | 0.0127 (7) | 0.0212 (8) |
N1 | 0.0367 (7) | 0.0356 (8) | 0.0383 (7) | 0.0008 (7) | 0.0023 (6) | 0.0010 (7) |
C2 | 0.0367 (9) | 0.0375 (9) | 0.0422 (9) | −0.0006 (8) | 0.0007 (7) | −0.0051 (9) |
C3 | 0.0331 (8) | 0.0449 (10) | 0.0423 (9) | −0.0035 (9) | 0.0067 (8) | 0.0003 (8) |
C4 | 0.0405 (9) | 0.0354 (9) | 0.0368 (8) | −0.0052 (9) | −0.0003 (7) | 0.0000 (8) |
C4A | 0.0362 (9) | 0.0316 (8) | 0.0338 (8) | −0.0043 (7) | −0.0008 (7) | −0.0042 (7) |
C5 | 0.0477 (10) | 0.0363 (9) | 0.0408 (8) | 0.0026 (9) | −0.0014 (9) | −0.0016 (8) |
C6 | 0.0414 (10) | 0.0456 (10) | 0.0538 (11) | 0.0097 (10) | 0.0030 (9) | −0.0086 (9) |
C7 | 0.0417 (10) | 0.0486 (11) | 0.0498 (10) | −0.0008 (9) | 0.0127 (9) | −0.0089 (10) |
C8 | 0.0453 (10) | 0.0368 (10) | 0.0444 (9) | −0.0054 (9) | 0.0097 (8) | −0.0053 (8) |
C8A | 0.0378 (9) | 0.0336 (9) | 0.0309 (8) | −0.0032 (8) | 0.0002 (7) | −0.0074 (7) |
C9 | 0.0441 (10) | 0.0405 (10) | 0.0425 (9) | 0.0026 (9) | 0.0027 (9) | 0.0074 (8) |
C10 | 0.0546 (11) | 0.0391 (10) | 0.0548 (11) | −0.0016 (10) | 0.0017 (11) | 0.0026 (10) |
Geometric parameters (Å, º) top
O1—C2 | 1.262 (2) | C5—H5 | 0.93 |
O2—C4 | 1.339 (2) | C6—C7 | 1.389 (3) |
O2—H2 | 0.82 | C6—H6 | 0.93 |
N1—C2 | 1.382 (2) | C7—C8 | 1.374 (3) |
N1—C8A | 1.402 (2) | C7—H7 | 0.93 |
N1—C9 | 1.471 (2) | C8—C8A | 1.407 (3) |
C2—C3 | 1.425 (3) | C8—H8 | 0.93 |
C3—C4 | 1.355 (3) | C9—C10 | 1.509 (3) |
C3—H3 | 0.93 | C9—H9A | 0.97 |
C4—C4A | 1.452 (2) | C9—H9B | 0.97 |
C4A—C5 | 1.403 (3) | C10—H10A | 0.96 |
C4A—C8A | 1.409 (2) | C10—H10B | 0.96 |
C5—C6 | 1.373 (3) | C10—H10C | 0.96 |
| | | |
C4—O2—H2 | 109.5 | C8—C7—C6 | 120.87 (18) |
C2—N1—C8A | 121.46 (15) | C8—C7—H7 | 119.6 |
C2—N1—C9 | 117.17 (15) | C6—C7—H7 | 119.6 |
C8A—N1—C9 | 121.27 (14) | C7—C8—C8A | 120.64 (18) |
O1—C2—N1 | 118.20 (16) | C7—C8—H8 | 119.7 |
O1—C2—C3 | 123.22 (17) | C8A—C8—H8 | 119.7 |
N1—C2—C3 | 118.58 (16) | N1—C8A—C8 | 121.77 (16) |
C4—C3—C2 | 121.75 (17) | N1—C8A—C4A | 119.90 (15) |
C4—C3—H3 | 119.1 | C8—C8A—C4A | 118.33 (17) |
C2—C3—H3 | 119.1 | N1—C9—C10 | 112.39 (15) |
O2—C4—C3 | 125.16 (17) | N1—C9—H9A | 109.1 |
O2—C4—C4A | 115.04 (16) | C10—C9—H9A | 109.1 |
C3—C4—C4A | 119.80 (16) | N1—C9—H9B | 109.1 |
C5—C4A—C8A | 119.80 (16) | C10—C9—H9B | 109.1 |
C5—C4A—C4 | 121.80 (16) | H9A—C9—H9B | 107.9 |
C8A—C4A—C4 | 118.40 (16) | C9—C10—H10A | 109.5 |
C6—C5—C4A | 120.64 (18) | C9—C10—H10B | 109.5 |
C6—C5—H5 | 119.7 | H10A—C10—H10B | 109.5 |
C4A—C5—H5 | 119.7 | C9—C10—H10C | 109.5 |
C5—C6—C7 | 119.72 (19) | H10A—C10—H10C | 109.5 |
C5—C6—H6 | 120.1 | H10B—C10—H10C | 109.5 |
C7—C6—H6 | 120.1 | | |
| | | |
C8A—N1—C2—O1 | 176.66 (16) | C5—C6—C7—C8 | 0.1 (3) |
C9—N1—C2—O1 | 0.3 (2) | C6—C7—C8—C8A | 0.0 (3) |
C8A—N1—C2—C3 | −3.8 (2) | C2—N1—C8A—C8 | −176.36 (16) |
C9—N1—C2—C3 | 179.85 (16) | C9—N1—C8A—C8 | −0.1 (2) |
O1—C2—C3—C4 | −179.11 (18) | C2—N1—C8A—C4A | 3.3 (2) |
N1—C2—C3—C4 | 1.3 (3) | C9—N1—C8A—C4A | 179.57 (15) |
C2—C3—C4—O2 | −179.71 (17) | C7—C8—C8A—N1 | 179.76 (16) |
C2—C3—C4—C4A | 1.5 (3) | C7—C8—C8A—C4A | 0.1 (3) |
O2—C4—C4A—C5 | −1.4 (2) | C5—C4A—C8A—N1 | −179.91 (16) |
C3—C4—C4A—C5 | 177.55 (17) | C4—C4A—C8A—N1 | −0.4 (2) |
O2—C4—C4A—C8A | 179.17 (15) | C5—C4A—C8A—C8 | −0.2 (2) |
C3—C4—C4A—C8A | −1.9 (2) | C4—C4A—C8A—C8 | 179.25 (16) |
C8A—C4A—C5—C6 | 0.3 (3) | C2—N1—C9—C10 | 86.8 (2) |
C4—C4A—C5—C6 | −179.17 (17) | C8A—N1—C9—C10 | −89.6 (2) |
C4A—C5—C6—C7 | −0.2 (3) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2···O1i | 0.82 | 1.76 | 2.580 (2) | 173 |
Symmetry code: (i) −x+1, y−1/2, −z+1/2. |