2-Methylquinolin-8-yl 2-nitrobenzoate

In the title compound, C₁₇H₁₂N₂O₄, the quinoline ring system is essentially planar. The ester group is twisted away from the quinoline ring system and nitro­benzene ring by 84.83 (3) and 80.56 (4)°, respectively. The crystal packing is stabilized by C—H...O inter­molecular hydrogen bonds, and π–π inter­actions between the quinoline ring systems of inversion-related mol­ecules, with a centroid–centroid distance of 3.6346 (6) Å.

Key indicators

• Single-crystal X-ray study
• T = 153 K
• Mean [sigma](C-C)= 0.002 Å
• R factor = 0.035
• wR factor = 0.103
• Data-to-parameter ratio = 15.6

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S1. Comment

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.

Related literature

For applications of quinoline benzoate derivatives, see: Zhang et al. (2005); Cheng et al. (2006).

S2. Experimental

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.

S3. Refinement

All H atoms were placed in calculated positions, with C—H = 0.95 or 0.98 Å, and refined using a riding model, with U_iso(H) = 1.2U_eq(C).

Computing details

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).

Figures

Fig. 1. The molecular structure of (I), showing 30% probability displacement ellipsoids.

2-Methylquinolin-8-yl 2-nitrobenzoate

Crystal data

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) Å^3

Data collection

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

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.035	H-atom parameters constrained
wR(F^2) = 0.103	w = 1/[σ^2(Fo^2) + (0.0656P)^2 + 0.1316P] where P = (Fo^2 + 2Fc^2)/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+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.081 (8)

Special details

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 (Ų)

	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)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

Geometric parameters (Å, º)

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)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O2^i	0.95	2.53	3.3790 (13)	148
C4—H4···O4^ii	0.95	2.49	3.4277 (13)	168
C6—H6···O4^iii	0.95	2.58	3.4965 (14)	163
C15—H15···O2^iv	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.