(E)-2-[2-(3-Nitro-phen-yl)ethen-yl]quinolin-8-ol.

In the title compound, C17H12N2O3, the mean planes of the benzene ring and the quinoline moiety are inclined to one another by 11.0 (1)°. The nitro substituent is twisted at an angle of 7.9 (2)° with respect to the attached benzene ring. Intra-molecular O-H⋯N and C-H⋯N hydrogen bonds occur. The crystal is constructed of mol-ecular stacks without involvement of π-stacking inter-actions, but showing inter-stack association via O-H⋯O and C-H⋯O hydrogen bonding. Thus, the supramolecular architecture of the crystal results from stacked molecules stabilized by hydrogen bonding between the stacks.

Related literature

For uses of quinolin-8-ol and derivatives as complexants and pharmaceuticals, see: Albrecht et al. (2008 ▶); Cacciatore et al. (2013 ▶); Desvignes & Leguen (1963 ▶); McMaster & Bruner (1935 ▶); Vögtle & Weber (1979 ▶); Weber & Vögtle (1975 ▶). For applications of stilbene and derivatives, see: Butkovic et al. (2011 ▶); Ho et al. (2000 ▶); Navadiya et al. (2008 ▶); Ravikrishnan et al. (2012 ▶); Waibel et al. (2009 ▶); Zhu et al. (2013 ▶). For the preparative method used for the synthesis of the title compound, see: Yuan et al. (2012 ▶). For non-classical hydrogen bonds, see: Desiraju & Steiner (1999 ▶). For related structures, including intra­molecular hydrogen bonding of quinolin-8-ol, see: Faza­eli et al. (2008 ▶); Malecki et al. (2010 ▶); Yoneda et al. (2002 ▶); Zeng et al. (2007 ▶).

Experimental

Crystal data

C17H12N2O3

M = 292.29

Monoclinic,

a = 20.3346 (7) Å

b = 4.7167 (1) Å

c = 15.5674 (6) Å

β = 109.255 (2)°

V = 1409.58 (8) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 298 K

0.54 × 0.24 × 0.06 mm

Data collection

Bruker X8 APEXII CCD detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2007 ▶) T min = 0.950, T max = 0.994

22418 measured reflections

2655 independent reflections

1768 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.065

wR(F 2) = 0.226

S = 1.03

2655 reflections

200 parameters

H-atom parameters constrained

Δρmax = 0.42 e Å−3

Δρmin = −0.24 e Å−3

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT-NT (Bruker, 2007 ▶); data reduction: SAINT-NT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶).

Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S1600536813027815/rn2119sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813027815/rn2119Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813027815/rn2119Isup3.cml

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

C17H12N2O3	F(000) = 608
Mr = 292.29	Dx = 1.377 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 20.3346 (7) Å	Cell parameters from 6524 reflections
b = 4.7167 (1) Å	θ = 2.6–24.8°
c = 15.5674 (6) Å	µ = 0.10 mm−1
β = 109.255 (2)°	T = 298 K
V = 1409.58 (8) Å3	Plate, colourless
Z = 4	0.54 × 0.24 × 0.06 mm

Bruker X8 APEXII CCD detector diffractometer	2655 independent reflections
Radiation source: fine-focus sealed tube	1768 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.028
phi and ω scans	θmax = 25.6°, θmin = 2.8°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −24→24
Tmin = 0.950, Tmax = 0.994	k = −4→5
22418 measured reflections	l = −18→18

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)] = 0.065	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.226	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.1192P)2 + 0.8405P] where P = (Fo2 + 2Fc2)/3
2655 reflections	(Δ/σ)max < 0.001
200 parameters	Δρmax = 0.42 e Å−3
0 restraints	Δρmin = −0.24 e Å−3

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	0.27846 (16)	0.0783 (7)	0.15082 (15)	0.1029 (10)
H1	0.2582	0.1861	0.1750	0.154*
O2	0.14581 (19)	1.0322 (8)	0.62596 (19)	0.1228 (12)
O3	0.0587 (2)	1.2936 (9)	0.5668 (2)	0.1474 (16)
N2	0.10391 (17)	1.1402 (7)	0.5616 (2)	0.0830 (9)
C1	0.33187 (19)	−0.0492 (8)	0.2157 (2)	0.0714 (9)
C2	0.3740 (2)	−0.2379 (8)	0.1950 (3)	0.0846 (11)
H2	0.3665	−0.2812	0.1342	0.101*
C3	0.4278 (2)	−0.3683 (8)	0.2610 (3)	0.0865 (11)
H3	0.4555	−0.4993	0.2444	0.104*
C4	0.44097 (17)	−0.3063 (7)	0.3524 (3)	0.0744 (9)
H4	0.4776	−0.3938	0.3969	0.089*
C5	0.39863 (14)	−0.1111 (6)	0.3769 (2)	0.0566 (7)
C6	0.40520 (16)	−0.0303 (6)	0.4665 (2)	0.0616 (8)
H6	0.4400	−0.1100	0.5153	0.074*
C7	0.36152 (15)	0.1611 (6)	0.48187 (18)	0.0565 (7)
H7	0.3666	0.2139	0.5413	0.068*
C8	0.30746 (14)	0.2841 (6)	0.40839 (16)	0.0489 (7)
N1	0.29937 (12)	0.2128 (5)	0.32357 (14)	0.0517 (6)
C9	0.34298 (14)	0.0229 (6)	0.30808 (17)	0.0517 (7)
C10	0.26019 (14)	0.4869 (6)	0.42662 (17)	0.0501 (7)
H10	0.2641	0.5191	0.4870	0.060*
C11	0.21158 (14)	0.6305 (6)	0.36290 (17)	0.0519 (7)
H11	0.2087	0.5966	0.3029	0.062*
C12	0.16274 (13)	0.8338 (6)	0.37686 (17)	0.0488 (6)
C13	0.15702 (14)	0.8923 (6)	0.46277 (17)	0.0547 (7)
H13	0.1858	0.8007	0.5144	0.066*
C14	0.10879 (15)	1.0851 (7)	0.4697 (2)	0.0602 (7)
C15	0.06455 (16)	1.2257 (7)	0.3969 (2)	0.0671 (8)
H15	0.0317	1.3532	0.4036	0.081*
C16	0.07075 (16)	1.1703 (7)	0.3126 (2)	0.0664 (8)
H16	0.0421	1.2653	0.2617	0.080*
C17	0.11795 (15)	0.9795 (6)	0.30281 (18)	0.0577 (7)
H17	0.1204	0.9455	0.2451	0.069*

	U11	U22	U33	U12	U13	U23
O1	0.130 (2)	0.125 (2)	0.0489 (13)	0.0300 (19)	0.0224 (14)	−0.0120 (14)
O2	0.145 (3)	0.165 (3)	0.0645 (16)	0.054 (2)	0.0430 (18)	0.0067 (18)
O3	0.154 (3)	0.200 (4)	0.101 (2)	0.091 (3)	0.058 (2)	−0.015 (2)
N2	0.088 (2)	0.100 (2)	0.0637 (18)	0.0185 (19)	0.0287 (16)	−0.0100 (17)
C1	0.086 (2)	0.076 (2)	0.0586 (18)	−0.0004 (18)	0.0330 (17)	−0.0096 (16)
C2	0.109 (3)	0.080 (2)	0.080 (2)	0.000 (2)	0.051 (2)	−0.0205 (19)
C3	0.094 (3)	0.061 (2)	0.128 (3)	−0.0008 (19)	0.068 (3)	−0.019 (2)
C4	0.0660 (19)	0.0581 (18)	0.105 (3)	0.0024 (15)	0.0357 (18)	0.0008 (18)
C5	0.0559 (15)	0.0470 (15)	0.0735 (19)	−0.0086 (13)	0.0305 (14)	−0.0034 (13)
C6	0.0623 (17)	0.0632 (17)	0.0550 (16)	−0.0050 (15)	0.0138 (14)	0.0103 (14)
C7	0.0643 (17)	0.0605 (16)	0.0432 (14)	−0.0020 (14)	0.0157 (12)	0.0030 (13)
C8	0.0577 (15)	0.0509 (14)	0.0379 (13)	−0.0130 (12)	0.0155 (11)	0.0006 (11)
N1	0.0581 (13)	0.0520 (12)	0.0461 (12)	−0.0026 (11)	0.0187 (10)	−0.0005 (10)
C9	0.0590 (16)	0.0519 (15)	0.0479 (14)	−0.0108 (13)	0.0226 (13)	−0.0018 (12)
C10	0.0565 (15)	0.0559 (15)	0.0389 (13)	−0.0047 (12)	0.0170 (12)	−0.0016 (11)
C11	0.0623 (15)	0.0545 (15)	0.0370 (12)	−0.0124 (13)	0.0139 (12)	−0.0015 (12)
C12	0.0520 (14)	0.0475 (14)	0.0474 (14)	−0.0085 (12)	0.0174 (11)	−0.0020 (11)
C13	0.0598 (16)	0.0580 (16)	0.0425 (14)	−0.0071 (13)	0.0117 (12)	0.0031 (12)
C14	0.0607 (16)	0.0646 (17)	0.0587 (17)	0.0003 (14)	0.0242 (14)	−0.0087 (14)
C15	0.0585 (17)	0.0667 (19)	0.071 (2)	0.0029 (15)	0.0138 (15)	−0.0071 (16)
C16	0.0622 (17)	0.0694 (19)	0.0592 (18)	0.0031 (16)	0.0085 (14)	−0.0013 (15)
C17	0.0622 (16)	0.0618 (17)	0.0430 (14)	−0.0091 (14)	0.0094 (13)	0.0013 (13)

O1—C1	1.356 (4)	C7—H7	0.9300
O1—H1	0.8200	C8—N1	1.319 (3)
O2—N2	1.195 (4)	C8—C10	1.449 (4)
O3—N2	1.194 (4)	N1—C9	1.337 (3)
N2—C14	1.488 (4)	C10—C11	1.332 (4)
C1—C2	1.346 (5)	C10—H10	0.9300
C1—C9	1.421 (4)	C11—C12	1.447 (4)
C2—C3	1.375 (6)	C11—H11	0.9300
C2—H2	0.9300	C12—C17	1.392 (4)
C3—C4	1.390 (5)	C12—C13	1.408 (4)
C3—H3	0.9300	C13—C14	1.368 (4)
C4—C5	1.396 (4)	C13—H13	0.9300
C4—H4	0.9300	C14—C15	1.365 (4)
C5—C6	1.410 (4)	C15—C16	1.384 (4)
C5—C9	1.424 (4)	C15—H15	0.9300
C6—C7	1.342 (4)	C16—C17	1.361 (4)
C6—H6	0.9300	C16—H16	0.9300
C7—C8	1.423 (4)	C17—H17	0.9300
C1—O1—H1	109.5	C8—N1—C9	118.7 (2)
O3—N2—O2	123.6 (3)	N1—C9—C1	116.7 (3)
O3—N2—C14	117.9 (3)	N1—C9—C5	124.8 (2)
O2—N2—C14	118.5 (3)	C1—C9—C5	118.5 (3)
C2—C1—O1	122.1 (3)	C11—C10—C8	124.6 (2)
C2—C1—C9	120.0 (3)	C11—C10—H10	117.7
O1—C1—C9	118.0 (3)	C8—C10—H10	117.7
C1—C2—C3	121.9 (3)	C10—C11—C12	127.1 (2)
C1—C2—H2	119.1	C10—C11—H11	116.5
C3—C2—H2	119.1	C12—C11—H11	116.5
C2—C3—C4	120.6 (3)	C17—C12—C13	117.0 (3)
C2—C3—H3	119.7	C17—C12—C11	119.8 (2)
C4—C3—H3	119.7	C13—C12—C11	123.3 (2)
C3—C4—C5	119.3 (3)	C14—C13—C12	119.5 (3)
C3—C4—H4	120.3	C14—C13—H13	120.3
C5—C4—H4	120.3	C12—C13—H13	120.3
C4—C5—C6	125.6 (3)	C15—C14—C13	123.4 (3)
C4—C5—C9	119.7 (3)	C15—C14—N2	118.6 (3)
C6—C5—C9	114.6 (3)	C13—C14—N2	118.0 (3)
C7—C6—C5	120.4 (3)	C14—C15—C16	117.0 (3)
C7—C6—H6	119.8	C14—C15—H15	121.5
C5—C6—H6	119.8	C16—C15—H15	121.5
C6—C7—C8	120.8 (3)	C17—C16—C15	121.3 (3)
C6—C7—H7	119.6	C17—C16—H16	119.3
C8—C7—H7	119.6	C15—C16—H16	119.3
N1—C8—C7	120.6 (3)	C16—C17—C12	121.8 (3)
N1—C8—C10	119.5 (2)	C16—C17—H17	119.1
C7—C8—C10	119.9 (2)	C12—C17—H17	119.1
O1—C1—C2—C3	−179.5 (4)	C4—C5—C9—C1	0.5 (4)
C9—C1—C2—C3	0.8 (6)	C6—C5—C9—C1	−179.1 (3)
C1—C2—C3—C4	−0.7 (6)	N1—C8—C10—C11	−6.3 (4)
C2—C3—C4—C5	0.5 (5)	C7—C8—C10—C11	174.4 (3)
C3—C4—C5—C6	179.2 (3)	C8—C10—C11—C12	179.6 (2)
C3—C4—C5—C9	−0.4 (4)	C10—C11—C12—C17	175.9 (3)
C4—C5—C6—C7	179.7 (3)	C10—C11—C12—C13	−4.9 (4)
C9—C5—C6—C7	−0.7 (4)	C17—C12—C13—C14	0.1 (4)
C5—C6—C7—C8	0.6 (4)	C11—C12—C13—C14	−179.2 (2)
C6—C7—C8—N1	−0.2 (4)	C12—C13—C14—C15	0.5 (4)
C6—C7—C8—C10	179.0 (2)	C12—C13—C14—N2	179.6 (3)
C7—C8—N1—C9	0.0 (4)	O3—N2—C14—C15	4.2 (5)
C10—C8—N1—C9	−179.2 (2)	O2—N2—C14—C15	−174.8 (4)
C8—N1—C9—C1	179.4 (2)	O3—N2—C14—C13	−175.0 (4)
C8—N1—C9—C5	−0.1 (4)	O2—N2—C14—C13	6.0 (5)
C2—C1—C9—N1	179.6 (3)	C13—C14—C15—C16	−1.2 (5)
O1—C1—C9—N1	0.0 (4)	N2—C14—C15—C16	179.7 (3)
C2—C1—C9—C5	−0.7 (5)	C14—C15—C16—C17	1.3 (5)
O1—C1—C9—C5	179.6 (3)	C15—C16—C17—C12	−0.8 (5)
C4—C5—C9—N1	−179.9 (3)	C13—C12—C17—C16	0.1 (4)
C6—C5—C9—N1	0.5 (4)	C11—C12—C17—C16	179.3 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	2.19	2.657 (3)	117
O1—H1···O2i	0.82	2.53	3.180 (5)	137
C10—H10···O1ii	0.93	2.51	3.400 (3)	160
C11—H11···N1	0.93	2.53	2.857 (4)	101

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.82	2.19	2.657 (3)	117
O1—H1⋯O2i	0.82	2.53	3.180 (5)	137
C10—H10⋯O1ii	0.93	2.51	3.400 (3)	160
C11—H11⋯N1	0.93	2.53	2.857 (4)	101

Symmetry codes: (i) ; (ii) .