1-(2-Methyl-6-nitro-4-phenyl-3-quinol-yl)ethanone.

In the title compound, C(18)H(14)N(2)O(3), the quinoline ring system is almost planar [maximum deviation = 0.013 (2) Å] and forms a dihedral angle of 60.36 (7)° with the benzene ring. The nitro group is slightly twisted from the attached quinoline ring system, forming a dihedral angle of 9.06 (19)°. In the crystal packing, inter-molecular C-H⋯O hydrogen bonds link the mol-ecules into chains propagating in [010].

Related literature

For related structures, see: Fun et al. (2009 ▶); Loh et al. (2009 ▶). For bond-length data, see: Allen et al. (1987 ▶). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C18H14N2O3

M = 306.31

Monoclinic,

a = 13.297 (2) Å

b = 7.7689 (12) Å

c = 17.9430 (19) Å

β = 129.099 (7)°

V = 1438.5 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 100 K

0.48 × 0.33 × 0.24 mm

Data collection

Bruker APEXII DUO CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.954, T max = 0.977

14926 measured reflections

4148 independent reflections

3310 reflections with I > 2σ(I)

R int = 0.035

Refinement

R[F 2 > 2σ(F 2)] = 0.061

wR(F 2) = 0.232

S = 1.13

4148 reflections

211 parameters

H-atom parameters constrained

Δρmax = 0.86 e Å−3

Δρmin = −0.78 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810015473/hb5399sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810015473/hb5399Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C18H14N2O3	F(000) = 640
Mr = 306.31	Dx = 1.414 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5914 reflections
a = 13.297 (2) Å	θ = 3.0–32.9°
b = 7.7689 (12) Å	µ = 0.10 mm−1
c = 17.9430 (19) Å	T = 100 K
β = 129.099 (7)°	Block, yellow
V = 1438.5 (3) Å3	0.48 × 0.33 × 0.24 mm
Z = 4

Bruker APEXII DUO CCD area-detector diffractometer	4148 independent reflections
Radiation source: fine-focus sealed tube	3310 reflections with I > 2σ(I)
graphite	Rint = 0.035
φ and ω scans	θmax = 30.0°, θmin = 3.0°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −18→18
Tmin = 0.954, Tmax = 0.977	k = −10→10
14926 measured reflections	l = −25→24

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)] = 0.061	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.232	H-atom parameters constrained
S = 1.13	w = 1/[σ2(Fo2) + (0.1525P)2 + 0.4637P] where P = (Fo2 + 2Fc2)/3
4148 reflections	(Δ/σ)max < 0.001
211 parameters	Δρmax = 0.86 e Å−3
0 restraints	Δρmin = −0.77 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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	0.22581 (15)	0.7458 (2)	0.39046 (10)	0.0262 (3)
O2	0.17169 (14)	1.20721 (18)	0.84191 (10)	0.0238 (3)
O3	0.35548 (14)	1.19938 (18)	0.86969 (10)	0.0229 (3)
N1	0.00896 (15)	0.73719 (17)	0.49922 (11)	0.0144 (3)
N2	0.24139 (16)	1.16058 (19)	0.82228 (11)	0.0169 (3)
C1	0.07078 (17)	0.6966 (2)	0.46604 (12)	0.0142 (3)
C2	0.07093 (16)	0.8420 (2)	0.57827 (12)	0.0133 (3)
C3	0.00244 (17)	0.8836 (2)	0.61256 (13)	0.0155 (3)
H3A	−0.0807	0.8404	0.5809	0.019*
C4	0.05691 (18)	0.9862 (2)	0.69126 (13)	0.0165 (3)
H4A	0.0124	1.0125	0.7140	0.020*
C5	0.18211 (17)	1.0511 (2)	0.73696 (12)	0.0149 (3)
C6	0.25169 (17)	1.0187 (2)	0.70594 (12)	0.0142 (3)
H6A	0.3334	1.0667	0.7374	0.017*
C7	0.19679 (16)	0.9106 (2)	0.62512 (12)	0.0132 (3)
C8	0.26215 (16)	0.8663 (2)	0.58772 (12)	0.0130 (3)
C9	0.19839 (17)	0.7586 (2)	0.50918 (12)	0.0141 (3)
C10	0.39210 (17)	0.9385 (2)	0.62955 (12)	0.0144 (3)
C11	0.50170 (17)	0.9063 (2)	0.72397 (13)	0.0165 (3)
H11A	0.4945	0.8404	0.7637	0.020*
C12	0.62200 (18)	0.9721 (2)	0.75941 (13)	0.0189 (4)
H12A	0.6946	0.9497	0.8225	0.023*
C13	0.63368 (18)	1.0716 (2)	0.70039 (14)	0.0190 (4)
H13A	0.7140	1.1152	0.7240	0.023*
C14	0.52518 (18)	1.1051 (2)	0.60658 (14)	0.0187 (4)
H14A	0.5328	1.1721	0.5674	0.022*
C15	0.40435 (18)	1.0389 (2)	0.57040 (13)	0.0173 (4)
H15A	0.3320	1.0612	0.5072	0.021*
C16	0.26170 (18)	0.6954 (2)	0.46785 (13)	0.0180 (4)
C17	0.3644 (2)	0.5611 (3)	0.52599 (15)	0.0257 (4)
H17A	0.4068	0.5403	0.4990	0.039*
H17B	0.3255	0.4564	0.5252	0.039*
H17C	0.4269	0.6005	0.5910	0.039*
C18	0.00164 (17)	0.5814 (2)	0.37966 (13)	0.0171 (3)
H18A	−0.0812	0.5498	0.3610	0.026*
H18B	0.0523	0.4796	0.3950	0.026*
H18C	−0.0104	0.6411	0.3277	0.026*

	U11	U22	U33	U12	U13	U23
O1	0.0330 (8)	0.0330 (8)	0.0241 (7)	−0.0058 (6)	0.0234 (7)	−0.0039 (6)
O2	0.0298 (8)	0.0284 (7)	0.0265 (7)	0.0043 (6)	0.0240 (7)	−0.0017 (5)
O3	0.0266 (7)	0.0256 (7)	0.0232 (7)	−0.0056 (5)	0.0189 (6)	−0.0054 (5)
N1	0.0177 (7)	0.0126 (6)	0.0182 (7)	0.0002 (5)	0.0139 (6)	0.0014 (5)
N2	0.0234 (8)	0.0166 (7)	0.0188 (7)	0.0026 (5)	0.0172 (6)	0.0017 (5)
C1	0.0183 (8)	0.0125 (7)	0.0168 (8)	−0.0002 (6)	0.0135 (7)	0.0006 (5)
C2	0.0163 (8)	0.0127 (7)	0.0165 (7)	0.0017 (5)	0.0131 (7)	0.0031 (5)
C3	0.0196 (8)	0.0139 (7)	0.0220 (8)	0.0009 (6)	0.0174 (7)	0.0025 (6)
C4	0.0237 (9)	0.0146 (7)	0.0227 (8)	0.0031 (6)	0.0202 (7)	0.0032 (6)
C5	0.0205 (8)	0.0138 (7)	0.0168 (8)	0.0019 (6)	0.0149 (7)	0.0014 (6)
C6	0.0176 (8)	0.0135 (7)	0.0182 (8)	0.0018 (6)	0.0144 (7)	0.0018 (6)
C7	0.0174 (8)	0.0126 (7)	0.0163 (8)	0.0019 (6)	0.0137 (7)	0.0023 (5)
C8	0.0144 (7)	0.0136 (7)	0.0160 (7)	0.0012 (5)	0.0120 (6)	0.0019 (5)
C9	0.0180 (8)	0.0140 (7)	0.0175 (8)	0.0004 (6)	0.0145 (7)	0.0006 (6)
C10	0.0177 (8)	0.0141 (7)	0.0191 (8)	−0.0014 (6)	0.0153 (7)	−0.0026 (6)
C11	0.0198 (8)	0.0175 (7)	0.0184 (8)	0.0002 (6)	0.0151 (7)	−0.0010 (6)
C12	0.0191 (8)	0.0208 (8)	0.0197 (8)	−0.0003 (6)	0.0136 (7)	−0.0020 (6)
C13	0.0191 (8)	0.0188 (8)	0.0280 (9)	−0.0033 (6)	0.0191 (8)	−0.0048 (6)
C14	0.0235 (9)	0.0173 (7)	0.0263 (9)	−0.0019 (6)	0.0209 (8)	−0.0011 (6)
C15	0.0212 (9)	0.0176 (7)	0.0198 (8)	0.0001 (6)	0.0161 (7)	0.0001 (6)
C16	0.0197 (8)	0.0207 (8)	0.0218 (9)	−0.0063 (6)	0.0170 (7)	−0.0076 (6)
C17	0.0224 (9)	0.0314 (10)	0.0269 (10)	0.0037 (7)	0.0173 (8)	−0.0067 (8)
C18	0.0199 (8)	0.0155 (7)	0.0200 (8)	−0.0020 (6)	0.0145 (7)	−0.0024 (6)

O1—C16	1.214 (2)	C9—C16	1.512 (2)
O2—N2	1.2352 (19)	C10—C11	1.394 (3)
O3—N2	1.220 (2)	C10—C15	1.407 (2)
N1—C1	1.322 (2)	C11—C12	1.393 (2)
N1—C2	1.371 (2)	C11—H11A	0.9300
N2—C5	1.472 (2)	C12—C13	1.397 (3)
C1—C9	1.433 (2)	C12—H12A	0.9300
C1—C18	1.500 (2)	C13—C14	1.386 (3)
C2—C7	1.420 (2)	C13—H13A	0.9300
C2—C3	1.421 (2)	C14—C15	1.397 (2)
C3—C4	1.365 (2)	C14—H14A	0.9300
C3—H3A	0.9300	C15—H15A	0.9300
C4—C5	1.406 (2)	C16—C17	1.499 (3)
C4—H4A	0.9300	C17—H17A	0.9600
C5—C6	1.371 (2)	C17—H17B	0.9600
C6—C7	1.416 (2)	C17—H17C	0.9600
C6—H6A	0.9300	C18—H18A	0.9600
C7—C8	1.435 (2)	C18—H18B	0.9600
C8—C9	1.378 (2)	C18—H18C	0.9600
C8—C10	1.493 (2)
C1—N1—C2	117.97 (14)	C11—C10—C8	122.36 (15)
O3—N2—O2	123.74 (15)	C15—C10—C8	118.50 (15)
O3—N2—C5	118.87 (13)	C12—C11—C10	120.56 (16)
O2—N2—C5	117.39 (15)	C12—C11—H11A	119.7
N1—C1—C9	122.51 (15)	C10—C11—H11A	119.7
N1—C1—C18	117.24 (15)	C11—C12—C13	120.11 (17)
C9—C1—C18	120.25 (14)	C11—C12—H12A	119.9
N1—C2—C7	123.38 (14)	C13—C12—H12A	119.9
N1—C2—C3	116.87 (15)	C14—C13—C12	119.78 (17)
C7—C2—C3	119.74 (15)	C14—C13—H13A	120.1
C4—C3—C2	120.92 (16)	C12—C13—H13A	120.1
C4—C3—H3A	119.5	C13—C14—C15	120.43 (16)
C2—C3—H3A	119.5	C13—C14—H14A	119.8
C3—C4—C5	118.26 (14)	C15—C14—H14A	119.8
C3—C4—H4A	120.9	C14—C15—C10	120.00 (17)
C5—C4—H4A	120.9	C14—C15—H15A	120.0
C6—C5—C4	123.46 (16)	C10—C15—H15A	120.0
C6—C5—N2	118.22 (15)	O1—C16—C17	123.29 (16)
C4—C5—N2	118.32 (14)	O1—C16—C9	121.18 (17)
C5—C6—C7	118.74 (16)	C17—C16—C9	115.44 (15)
C5—C6—H6A	120.6	C16—C17—H17A	109.5
C7—C6—H6A	120.6	C16—C17—H17B	109.5
C6—C7—C2	118.85 (14)	H17A—C17—H17B	109.5
C6—C7—C8	123.23 (15)	C16—C17—H17C	109.5
C2—C7—C8	117.91 (15)	H17A—C17—H17C	109.5
C9—C8—C7	117.43 (15)	H17B—C17—H17C	109.5
C9—C8—C10	120.86 (14)	C1—C18—H18A	109.5
C7—C8—C10	121.67 (14)	C1—C18—H18B	109.5
C8—C9—C1	120.78 (14)	H18A—C18—H18B	109.5
C8—C9—C16	121.66 (15)	C1—C18—H18C	109.5
C1—C9—C16	117.51 (14)	H18A—C18—H18C	109.5
C11—C10—C15	119.12 (16)	H18B—C18—H18C	109.5
C2—N1—C1—C9	−0.4 (2)	C7—C8—C9—C1	1.1 (2)
C2—N1—C1—C18	179.85 (14)	C10—C8—C9—C1	−176.71 (15)
C1—N1—C2—C7	0.9 (2)	C7—C8—C9—C16	−176.30 (15)
C1—N1—C2—C3	−179.96 (14)	C10—C8—C9—C16	5.9 (2)
N1—C2—C3—C4	179.55 (15)	N1—C1—C9—C8	−0.7 (3)
C7—C2—C3—C4	−1.3 (2)	C18—C1—C9—C8	179.11 (15)
C2—C3—C4—C5	0.6 (2)	N1—C1—C9—C16	176.82 (15)
C3—C4—C5—C6	0.9 (3)	C18—C1—C9—C16	−3.4 (2)
C3—C4—C5—N2	−179.50 (15)	C9—C8—C10—C11	−119.51 (18)
O3—N2—C5—C6	−9.7 (2)	C7—C8—C10—C11	62.8 (2)
O2—N2—C5—C6	170.71 (15)	C9—C8—C10—C15	58.8 (2)
O3—N2—C5—C4	170.68 (15)	C7—C8—C10—C15	−118.90 (17)
O2—N2—C5—C4	−8.9 (2)	C15—C10—C11—C12	−0.2 (2)
C4—C5—C6—C7	−1.7 (3)	C8—C10—C11—C12	178.13 (15)
N2—C5—C6—C7	178.71 (14)	C10—C11—C12—C13	0.1 (3)
C5—C6—C7—C2	0.9 (2)	C11—C12—C13—C14	0.2 (3)
C5—C6—C7—C8	−179.01 (15)	C12—C13—C14—C15	−0.5 (3)
N1—C2—C7—C6	179.57 (15)	C13—C14—C15—C10	0.5 (3)
C3—C2—C7—C6	0.5 (2)	C11—C10—C15—C14	−0.1 (2)
N1—C2—C7—C8	−0.5 (2)	C8—C10—C15—C14	−178.50 (15)
C3—C2—C7—C8	−179.57 (14)	C8—C9—C16—O1	−109.8 (2)
C6—C7—C8—C9	179.40 (15)	C1—C9—C16—O1	72.7 (2)
C2—C7—C8—C9	−0.6 (2)	C8—C9—C16—C17	73.6 (2)
C6—C7—C8—C10	−2.8 (2)	C1—C9—C16—C17	−103.90 (19)
C2—C7—C8—C10	177.24 (14)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3A···O2i	0.93	2.56	3.208 (3)	127

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3A⋯O2i	0.93	2.56	3.208 (3)	127

Symmetry code: (i) .