Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807049069/ci2478sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807049069/ci2478Isup2.hkl |
CCDC reference: 667347
Key indicators
- Single-crystal X-ray study
- T = 153 K
- Mean (C-C)= 0.002 Å
- R factor = 0.035
- wR factor = 0.103
- Data-to-parameter ratio = 15.6
checkCIF/PLATON results
No syntax errors found No errors found in this datablock
For applications of quinoline benzoate derivatives, see: Zhang et al. (2005); Cheng et al. (2006).
Compound (I) was prepared according to the procedure of Zhang et al. (2005). Colourless single crystals suitable for X-ray diffraction were obtained by recrystallization from ethyl acetate.
All H atoms were placed in calculated positions, with C—H = 0.95 or 0.98 Å, and refined using a riding model, with Uiso(H) = 1.2Ueq(C).
8-Hydroxyquinoline benzoate derivatives are a class of chemosensors for metal ions (Zhang et al., 2005; Cheng et al., 2006). We report here the crystal structure of the title compound, (I).
Bond lengths and angles in (I) are normal. The quinoline ring system is planar, with a maximum deviation of 0.019 (4) Å for atom C3. The ester group is twisted away from the planes of the attached rings (Fig. 1). The dihedral angle between the N1/C2—C10 and O1/O2/C12/C13 planes is 84.83 (3)°, and that between O1/O2/C12/C13 and C13—C18 planes is 80.56 (4)°. The C13—C18 and N2/O3/O4/C18 planes form a dihedral angle of 13.18 (4)°. The crystal packing is stabilized by C—H···O hydrogen bonds (Table 1), and π-π interactions between the quinoline ring systems of the inversion-related molecules at (x, y, z) and (1 - x, 1 - y, -z), with a centroid–centroid distance of 3.6346 (6) Å.
For applications of quinoline benzoate derivatives, see: Zhang et al. (2005); Cheng et al. (2006).
Data collection: RAPID-AUTO (Rigaku, 2004); cell refinement: RAPID-AUTO (Rigaku, 2004); data reduction: RAPID-AUTO (Rigaku, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).
Fig. 1. The molecular structure of (I), showing 30% probability displacement ellipsoids. |
C17H12N2O4 | Z = 2 |
Mr = 308.29 | F(000) = 320 |
Triclinic, P1 | Dx = 1.418 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 7.6661 (4) Å | Cell parameters from 6275 reflections |
b = 8.1331 (3) Å | θ = 3.3–27.5° |
c = 12.3871 (5) Å | µ = 0.10 mm−1 |
α = 95.979 (1)° | T = 153 K |
β = 105.389 (2)° | Block, colourless |
γ = 100.749 (1)° | 0.58 × 0.54 × 0.35 mm |
V = 721.88 (6) Å3 |
Rigaku R-AXIS RAPID diffractometer | 2892 reflections with I > 2σ(I) |
Radiation source: Rotating Anode | Rint = 0.019 |
Graphite monochromator | θmax = 27.5°, θmin = 3.3° |
ω scans | h = −9→9 |
7096 measured reflections | k = −9→10 |
3266 independent reflections | l = −16→13 |
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)] = 0.035 | H-atom parameters constrained |
wR(F2) = 0.103 | w = 1/[σ2(Fo2) + (0.0656P)2 + 0.1316P] where P = (Fo2 + 2Fc2)/3 |
S = 1.00 | (Δ/σ)max = 0.001 |
3266 reflections | Δρmax = 0.30 e Å−3 |
210 parameters | Δρmin = −0.21 e Å−3 |
0 restraints | Extinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.081 (8) |
C17H12N2O4 | γ = 100.749 (1)° |
Mr = 308.29 | V = 721.88 (6) Å3 |
Triclinic, P1 | Z = 2 |
a = 7.6661 (4) Å | Mo Kα radiation |
b = 8.1331 (3) Å | µ = 0.10 mm−1 |
c = 12.3871 (5) Å | T = 153 K |
α = 95.979 (1)° | 0.58 × 0.54 × 0.35 mm |
β = 105.389 (2)° |
Rigaku R-AXIS RAPID diffractometer | 2892 reflections with I > 2σ(I) |
7096 measured reflections | Rint = 0.019 |
3266 independent reflections |
R[F2 > 2σ(F2)] = 0.035 | 0 restraints |
wR(F2) = 0.103 | H-atom parameters constrained |
S = 1.00 | Δρmax = 0.30 e Å−3 |
3266 reflections | Δρmin = −0.21 e Å−3 |
210 parameters |
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 | ||
O1 | 0.73507 (9) | 0.38524 (8) | 0.30774 (6) | 0.02379 (18) | |
O2 | 0.60868 (9) | 0.12003 (9) | 0.32654 (6) | 0.02626 (18) | |
O3 | 0.77544 (12) | 0.34184 (12) | 0.55498 (7) | 0.0408 (2) | |
O4 | 0.96676 (13) | 0.26474 (12) | 0.69219 (6) | 0.0402 (2) | |
N1 | 0.66377 (12) | 0.25217 (10) | 0.08459 (7) | 0.0239 (2) | |
N2 | 0.91199 (12) | 0.28391 (11) | 0.59306 (7) | 0.0267 (2) | |
C2 | 0.62798 (15) | 0.18862 (12) | −0.02351 (9) | 0.0274 (2) | |
C3 | 0.46019 (17) | 0.19190 (14) | −0.10690 (9) | 0.0332 (3) | |
H3 | 0.4387 | 0.1427 | −0.1836 | 0.040* | |
C4 | 0.33156 (16) | 0.26503 (14) | −0.07696 (9) | 0.0321 (3) | |
H4 | 0.2204 | 0.2687 | −0.1325 | 0.038* | |
C5 | 0.23707 (15) | 0.41284 (14) | 0.07774 (10) | 0.0313 (2) | |
H5 | 0.1245 | 0.4210 | 0.0255 | 0.038* | |
C6 | 0.27352 (15) | 0.47534 (14) | 0.19005 (10) | 0.0319 (2) | |
H6 | 0.1864 | 0.5261 | 0.2154 | 0.038* | |
C7 | 0.44085 (15) | 0.46453 (13) | 0.26868 (9) | 0.0273 (2) | |
H7 | 0.4665 | 0.5073 | 0.3469 | 0.033* | |
C8 | 0.56502 (13) | 0.39205 (12) | 0.23104 (8) | 0.0226 (2) | |
C9 | 0.53342 (13) | 0.32493 (11) | 0.11554 (8) | 0.0221 (2) | |
C10 | 0.36400 (14) | 0.33626 (12) | 0.03803 (9) | 0.0261 (2) | |
C11 | 0.77083 (18) | 0.11101 (14) | −0.05889 (10) | 0.0357 (3) | |
H11A | 0.8732 | 0.1112 | 0.0083 | 0.043* | |
H11B | 0.8185 | 0.1769 | −0.1109 | 0.043* | |
H11C | 0.7143 | −0.0059 | −0.0972 | 0.043* | |
C12 | 0.74052 (13) | 0.23497 (12) | 0.34368 (7) | 0.0198 (2) | |
C13 | 0.93617 (13) | 0.22311 (12) | 0.39880 (8) | 0.0209 (2) | |
C14 | 1.03825 (14) | 0.18029 (14) | 0.32710 (9) | 0.0286 (2) | |
H14 | 0.9882 | 0.1720 | 0.2474 | 0.034* | |
C15 | 1.21351 (15) | 0.14958 (15) | 0.37172 (11) | 0.0338 (3) | |
H15 | 1.2825 | 0.1204 | 0.3222 | 0.041* | |
C16 | 1.28816 (14) | 0.16115 (14) | 0.48743 (11) | 0.0340 (3) | |
H16 | 1.4079 | 0.1396 | 0.5170 | 0.041* | |
C17 | 1.18880 (14) | 0.20419 (13) | 0.56056 (9) | 0.0290 (2) | |
H17 | 1.2391 | 0.2122 | 0.6403 | 0.035* | |
C18 | 1.01464 (13) | 0.23525 (12) | 0.51498 (8) | 0.0224 (2) |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0232 (4) | 0.0227 (4) | 0.0204 (3) | 0.0044 (3) | −0.0019 (3) | 0.0041 (2) |
O2 | 0.0197 (3) | 0.0278 (4) | 0.0308 (4) | 0.0054 (3) | 0.0051 (3) | 0.0086 (3) |
O3 | 0.0394 (5) | 0.0640 (6) | 0.0249 (4) | 0.0296 (4) | 0.0077 (3) | 0.0043 (4) |
O4 | 0.0487 (5) | 0.0538 (5) | 0.0171 (4) | 0.0174 (4) | 0.0036 (3) | 0.0056 (3) |
N1 | 0.0266 (4) | 0.0210 (4) | 0.0224 (4) | 0.0047 (3) | 0.0040 (3) | 0.0048 (3) |
N2 | 0.0285 (4) | 0.0304 (5) | 0.0180 (4) | 0.0073 (3) | 0.0019 (3) | 0.0014 (3) |
C2 | 0.0351 (6) | 0.0203 (5) | 0.0246 (5) | 0.0027 (4) | 0.0068 (4) | 0.0044 (4) |
C3 | 0.0446 (6) | 0.0275 (5) | 0.0196 (5) | 0.0020 (4) | 0.0007 (4) | 0.0022 (4) |
C4 | 0.0330 (6) | 0.0306 (5) | 0.0228 (5) | 0.0026 (4) | −0.0061 (4) | 0.0067 (4) |
C5 | 0.0231 (5) | 0.0299 (5) | 0.0377 (6) | 0.0082 (4) | −0.0005 (4) | 0.0115 (4) |
C6 | 0.0282 (5) | 0.0299 (5) | 0.0410 (6) | 0.0122 (4) | 0.0099 (5) | 0.0108 (4) |
C7 | 0.0308 (5) | 0.0247 (5) | 0.0266 (5) | 0.0074 (4) | 0.0070 (4) | 0.0056 (4) |
C8 | 0.0220 (5) | 0.0202 (4) | 0.0219 (5) | 0.0041 (3) | −0.0001 (4) | 0.0059 (3) |
C9 | 0.0228 (5) | 0.0188 (4) | 0.0218 (5) | 0.0035 (3) | 0.0012 (4) | 0.0057 (3) |
C10 | 0.0257 (5) | 0.0223 (5) | 0.0249 (5) | 0.0033 (4) | −0.0016 (4) | 0.0076 (4) |
C11 | 0.0462 (7) | 0.0295 (6) | 0.0336 (6) | 0.0074 (5) | 0.0171 (5) | 0.0029 (4) |
C12 | 0.0217 (4) | 0.0241 (5) | 0.0143 (4) | 0.0074 (3) | 0.0050 (3) | 0.0025 (3) |
C13 | 0.0188 (4) | 0.0215 (4) | 0.0215 (5) | 0.0040 (3) | 0.0040 (3) | 0.0049 (3) |
C14 | 0.0258 (5) | 0.0352 (6) | 0.0278 (5) | 0.0077 (4) | 0.0111 (4) | 0.0079 (4) |
C15 | 0.0251 (5) | 0.0378 (6) | 0.0451 (7) | 0.0098 (4) | 0.0179 (5) | 0.0104 (5) |
C16 | 0.0174 (5) | 0.0335 (6) | 0.0502 (7) | 0.0077 (4) | 0.0051 (4) | 0.0110 (5) |
C17 | 0.0225 (5) | 0.0284 (5) | 0.0299 (5) | 0.0040 (4) | −0.0021 (4) | 0.0061 (4) |
C18 | 0.0208 (5) | 0.0218 (5) | 0.0212 (5) | 0.0033 (3) | 0.0020 (4) | 0.0026 (3) |
O1—C12 | 1.3476 (11) | C7—C8 | 1.3633 (14) |
O1—C8 | 1.4091 (11) | C7—H7 | 0.95 |
O2—C12 | 1.1970 (12) | C8—C9 | 1.4169 (13) |
O3—N2 | 1.2282 (11) | C9—C10 | 1.4208 (13) |
O4—N2 | 1.2244 (11) | C11—H11A | 0.98 |
N1—C2 | 1.3203 (13) | C11—H11B | 0.98 |
N1—C9 | 1.3683 (13) | C11—H11C | 0.98 |
N2—C18 | 1.4669 (13) | C12—C13 | 1.4998 (12) |
C2—C3 | 1.4268 (15) | C13—C14 | 1.3887 (14) |
C2—C11 | 1.4982 (16) | C13—C18 | 1.3898 (13) |
C3—C4 | 1.3530 (17) | C14—C15 | 1.3903 (15) |
C3—H3 | 0.95 | C14—H14 | 0.95 |
C4—C10 | 1.4187 (15) | C15—C16 | 1.3811 (17) |
C4—H4 | 0.95 | C15—H15 | 0.95 |
C5—C6 | 1.3658 (17) | C16—C17 | 1.3868 (16) |
C5—C10 | 1.4117 (16) | C16—H16 | 0.95 |
C5—H5 | 0.95 | C17—C18 | 1.3859 (13) |
C6—C7 | 1.4138 (14) | C17—H17 | 0.95 |
C6—H6 | 0.95 | ||
C12—O1—C8 | 114.97 (7) | C5—C10—C9 | 119.76 (9) |
C2—N1—C9 | 117.53 (9) | C4—C10—C9 | 116.60 (10) |
O4—N2—O3 | 123.68 (9) | C2—C11—H11A | 109.5 |
O4—N2—C18 | 118.44 (8) | C2—C11—H11B | 109.5 |
O3—N2—C18 | 117.88 (8) | H11A—C11—H11B | 109.5 |
N1—C2—C3 | 122.62 (10) | C2—C11—H11C | 109.5 |
N1—C2—C11 | 118.09 (10) | H11A—C11—H11C | 109.5 |
C3—C2—C11 | 119.29 (10) | H11B—C11—H11C | 109.5 |
C4—C3—C2 | 120.10 (10) | O2—C12—O1 | 124.81 (8) |
C4—C3—H3 | 120.0 | O2—C12—C13 | 123.67 (8) |
C2—C3—H3 | 120.0 | O1—C12—C13 | 111.29 (8) |
C3—C4—C10 | 119.46 (10) | C14—C13—C18 | 118.23 (9) |
C3—C4—H4 | 120.3 | C14—C13—C12 | 116.83 (8) |
C10—C4—H4 | 120.3 | C18—C13—C12 | 124.62 (8) |
C6—C5—C10 | 121.08 (9) | C13—C14—C15 | 120.16 (10) |
C6—C5—H5 | 119.5 | C13—C14—H14 | 119.9 |
C10—C5—H5 | 119.5 | C15—C14—H14 | 119.9 |
C5—C6—C7 | 120.06 (10) | C16—C15—C14 | 120.61 (10) |
C5—C6—H6 | 120.0 | C16—C15—H15 | 119.7 |
C7—C6—H6 | 120.0 | C14—C15—H15 | 119.7 |
C8—C7—C6 | 119.32 (10) | C15—C16—C17 | 120.17 (9) |
C8—C7—H7 | 120.3 | C15—C16—H16 | 119.9 |
C6—C7—H7 | 120.3 | C17—C16—H16 | 119.9 |
C7—C8—O1 | 120.01 (9) | C18—C17—C16 | 118.62 (10) |
C7—C8—C9 | 122.77 (9) | C18—C17—H17 | 120.7 |
O1—C8—C9 | 117.21 (8) | C16—C17—H17 | 120.7 |
N1—C9—C8 | 119.31 (8) | C17—C18—C13 | 122.21 (9) |
N1—C9—C10 | 123.67 (9) | C17—C18—N2 | 118.26 (9) |
C8—C9—C10 | 117.01 (9) | C13—C18—N2 | 119.52 (8) |
C5—C10—C4 | 123.62 (10) | ||
C9—N1—C2—C3 | −0.68 (15) | N1—C9—C10—C4 | 0.80 (14) |
C9—N1—C2—C11 | 179.05 (9) | C8—C9—C10—C4 | −178.51 (9) |
N1—C2—C3—C4 | 1.30 (16) | C8—O1—C12—O2 | −9.72 (13) |
C11—C2—C3—C4 | −178.44 (10) | C8—O1—C12—C13 | 164.90 (8) |
C2—C3—C4—C10 | −0.80 (16) | O2—C12—C13—C14 | 93.64 (11) |
C10—C5—C6—C7 | 0.22 (16) | O1—C12—C13—C14 | −81.05 (10) |
C5—C6—C7—C8 | 0.32 (15) | O2—C12—C13—C18 | −79.68 (13) |
C6—C7—C8—O1 | 177.95 (8) | O1—C12—C13—C18 | 105.63 (10) |
C6—C7—C8—C9 | −0.53 (15) | C18—C13—C14—C15 | 0.46 (15) |
C12—O1—C8—C7 | 99.86 (10) | C12—C13—C14—C15 | −173.31 (9) |
C12—O1—C8—C9 | −81.58 (10) | C13—C14—C15—C16 | 0.01 (16) |
C2—N1—C9—C8 | 178.93 (8) | C14—C15—C16—C17 | −0.19 (17) |
C2—N1—C9—C10 | −0.37 (14) | C15—C16—C17—C18 | −0.11 (16) |
C7—C8—C9—N1 | −179.16 (9) | C16—C17—C18—C13 | 0.61 (15) |
O1—C8—C9—N1 | 2.33 (13) | C16—C17—C18—N2 | −178.83 (9) |
C7—C8—C9—C10 | 0.19 (14) | C14—C13—C18—C17 | −0.78 (14) |
O1—C8—C9—C10 | −178.32 (8) | C12—C13—C18—C17 | 172.46 (9) |
C6—C5—C10—C4 | 178.22 (10) | C14—C13—C18—N2 | 178.66 (9) |
C6—C5—C10—C9 | −0.55 (16) | C12—C13—C18—N2 | −8.10 (14) |
C3—C4—C10—C5 | −178.99 (10) | O4—N2—C18—C17 | −13.43 (14) |
C3—C4—C10—C9 | −0.18 (15) | O3—N2—C18—C17 | 166.56 (9) |
N1—C9—C10—C5 | 179.66 (9) | O4—N2—C18—C13 | 167.11 (9) |
C8—C9—C10—C5 | 0.35 (14) | O3—N2—C18—C13 | −12.90 (14) |
D—H···A | D—H | H···A | D···A | D—H···A |
C3—H3···O2i | 0.95 | 2.53 | 3.3790 (13) | 148 |
C4—H4···O4ii | 0.95 | 2.49 | 3.4277 (13) | 168 |
C6—H6···O4iii | 0.95 | 2.58 | 3.4965 (14) | 163 |
C15—H15···O2iv | 0.95 | 2.49 | 3.2698 (12) | 140 |
Symmetry codes: (i) −x+1, −y, −z; (ii) x−1, y, z−1; (iii) −x+1, −y+1, −z+1; (iv) x+1, y, z. |
Experimental details
Crystal data | |
Chemical formula | C17H12N2O4 |
Mr | 308.29 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 153 |
a, b, c (Å) | 7.6661 (4), 8.1331 (3), 12.3871 (5) |
α, β, γ (°) | 95.979 (1), 105.389 (2), 100.749 (1) |
V (Å3) | 721.88 (6) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.10 |
Crystal size (mm) | 0.58 × 0.54 × 0.35 |
Data collection | |
Diffractometer | Rigaku R-AXIS RAPID |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 7096, 3266, 2892 |
Rint | 0.019 |
(sin θ/λ)max (Å−1) | 0.649 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.035, 0.103, 1.00 |
No. of reflections | 3266 |
No. of parameters | 210 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.30, −0.21 |
Computer programs: RAPID-AUTO (Rigaku, 2004), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), XP in SHELXTL (Bruker, 1997).
D—H···A | D—H | H···A | D···A | D—H···A |
C3—H3···O2i | 0.95 | 2.53 | 3.3790 (13) | 148 |
C4—H4···O4ii | 0.95 | 2.49 | 3.4277 (13) | 168 |
C6—H6···O4iii | 0.95 | 2.58 | 3.4965 (14) | 163 |
C15—H15···O2iv | 0.95 | 2.49 | 3.2698 (12) | 140 |
Symmetry codes: (i) −x+1, −y, −z; (ii) x−1, y, z−1; (iii) −x+1, −y+1, −z+1; (iv) x+1, y, z. |
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8-Hydroxyquinoline benzoate derivatives are a class of chemosensors for metal ions (Zhang et al., 2005; Cheng et al., 2006). We report here the crystal structure of the title compound, (I).
Bond lengths and angles in (I) are normal. The quinoline ring system is planar, with a maximum deviation of 0.019 (4) Å for atom C3. The ester group is twisted away from the planes of the attached rings (Fig. 1). The dihedral angle between the N1/C2—C10 and O1/O2/C12/C13 planes is 84.83 (3)°, and that between O1/O2/C12/C13 and C13—C18 planes is 80.56 (4)°. The C13—C18 and N2/O3/O4/C18 planes form a dihedral angle of 13.18 (4)°. The crystal packing is stabilized by C—H···O hydrogen bonds (Table 1), and π-π interactions between the quinoline ring systems of the inversion-related molecules at (x, y, z) and (1 - x, 1 - y, -z), with a centroid–centroid distance of 3.6346 (6) Å.