(E)-2-[2-(3-Nitro­phen­yl)ethen­yl]quinolin-8-ol

Schulze, M.; Seichter, W.; Weber, E.

doi:10.1107/S1600536813027815

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 69| Part 11| November 2013| Pages o1651-o1652

doi:10.1107/S1600536813027815

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(E)-2-[2-(3-Nitrophenyl)ethenyl]quinolin-8-ol

Mathias Schulze,^a Wilhelm Seichter ^a and Edwin Weber ^a ^*

^aInstitut für Organische Chemie, TU Bergakademie Freiberg, Leipziger Strasse 29, D-09596 Freiberg/Sachsen, Germany
^*Correspondence e-mail: edwin.weber@chemie.tu-freiberg.de

(Received 30 August 2013; accepted 10 October 2013; online 16 October 2013)

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. Intramolecular O—H⋯N and C—H⋯N hydrogen bonds occur. The crystal is constructed of molecular stacks without involvement of π-stacking interactions, but showing interstack 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.

CCDC reference: 965730

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_r = 292.29
Monoclinic, P 2₁ /c
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[F² > 2σ(F²)] = 0.065
wR(F²) = 0.226
S = 1.03
2655 reflections
200 parameters
H-atom parameters constrained
Δρ_max = 0.42 e Å⁻³
Δρ_min = −0.24 e Å⁻³

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) $[x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ ; (ii) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

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).

Supporting information

CCDC reference: 965730

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: 10.1107/S1600536813027815/rn2119sup1.cif

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

Supporting information file. DOI: 10.1107/S1600536813027815/rn2119Isup3.cml

checkCIF report

Comment top

Quinolin-8-ol (8-hydroxyquinoline) is a well known complexant for a variety of transition metal ions forming quantitatively precipitable internal complexes thus playing an important role in analytical chemistry (Albrecht et al., 2008). Derivatives of quinolin-8-ol have also been used as an active component in the design of alkali and alkaline earth metal ion complexing ligands (Vögtle & Weber, 1979; Weber & Vögtle, 1975). Moreover, quinolin-8-ol shows strong fungicidal and antiseptic effects (Desvignes & Leguen, 1963) and derivatives of which are drugs for the successful treatment of different diseases (Cacciatore et al., 2013; McMaster & Bruner, 1935). On the other hand, stilbene and its derivatives are starting materials for the preparation of various dyes, optical brighteners, liquid crystalline compounds and synthetic estrogens (Navadiya et al., 2008; Ravikrishnan et al., 2012; Waibel et al., 2009; Zhu et al., 2013). They are also of interest due to their particular stereochemistry including photochemical rearrangement and reactions (Butkovic et al., 2011; Ho et al., 2000). The structure of the title compound comprises both these specific construction elements, quinolin-8-ol and stilbene. In the structure of the compound (Fig. 1), the dihedral angle formed by the least-squares planes of the phenyl ring and the quinoline moiety is 11.0 (1)°, while the nitro substituent is twisted at an angle of 7.9 (2)° with reference to the phenyl ring. The bond lengths within the quinoline fragment are in the range of expected values and agree well with those found in the crystal structures of related compounds (Yoneda et al., 2002; Zeng et al., 2007). The torsion angle along the atomic sequence N(1)—C(8)—C(10)—C(11) is 6.3 (4)°. Within the quinolin-8-ol part, the hydroxyl hydrogen is connected to the nitrogen by a strained hydrogen bond [O(1)—H(1)···N(1) 2.19Å, 117°] which is typical for this kind of compounds (Fazaeli et al., 2008; Malecki et al., 2010; Zeng et al., 2007). Moreover, there is a hydrogen bond type contact between H(11) and N(1) [d(H···N) 2.53Å]. The crystal (Fig. 2) is constructed of molecular stacks extending along the b-axis. The closest centroid-centroid distance between the phenol and pyridine ring of consecutive molecules is 4.02Å thus indicating, however, no π-stacking interaction between those groups. Moreover, the ethenylene fragment of a given molecule is sandwiched in a distance of ca. 3.45Å between the electron deficient aromatic rings of adjacent molecules. Interstack association is accomplished by a close network of O—H···O [d(O···O) 3.180 (5)Å] and C—H···O hydrogen bonds [d(C···O) 3.400 (3)Å] (Desiraju & Steiner, 1999).

Related literature top

For uses of quinoline-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 quinoline-8-ol, see: Fazaeli et al. (2008); Malecki et al. (2010); Yoneda et al. (2002); Zeng et al. (2007).

Experimental top

The title compound was synthesized via Knoevenagel type condensation (Yuan et al., 2012) using 8-hydroxyquinaldine (320 mg, 2.0 mmol) and 4-nitrobenzaldehyde (1.21 g, 8.0 mmol) in acetic anhydride (100 ml). The mixture was stirred for 30 h under reflux. After removal of the solvent, the residue was dissolved in 100 ml of pyridine/water (v/v = 4:1) and heated at 100° for 1 h. Evaporation of the solvent under vacuum and purification of the crude product by recrystallization from ethanol yielded 230 mg (40%) of yellow crystals determined as the E configurated compound by ¹H NMR analysis (ethenylene protons); m. p. = 449 K. IR (KBr) 3410, 3081, 1526, 1348, 1238, 1196, 829, 735, 593. ¹H NMR (500 MHz, CDCl₃) 7.20 (d, ³J_HH = 7.5 Hz, 1 H), 7.33 (d, ³J_HH = 8.2 Hz, 1 H), 7.51 - 7.39 (m, 2 H), 7.59 (t, ³J_HH = 7.9 Hz, 1 H), 7.65 (d, ³J_HH = 8.5 Hz, 1 H), 7.77 (d, ³J_HH = 16.1 Hz, 1 H), 7.92 (d, ³J_HH = 7.7 Hz, 1 H), 8.17 (³J_HH = 8.0 Hz, 1 H), 8.19 (³J_HH = 4.7 Hz, 1 H), 8.49 (s, 1 H). ¹³C NMR (126 MHz, CDCl₃) 110.4, 117.7, 120.61, 121.6, 123.04, 127.8, 127.9, 129.8, 131.0, 131.5, 132.9, 136.8, 138.1, 138.3, 148.8, 152.2, 152.5. MS (ESI) m/z: found 293.0 [M+H]+; calc. for C₁₇H₁₂N₂O₃ 292.08. The melting point (uncorrected) was measured on a hot stage microscope (Büchi 510). The IR spectrum was recorded on a Perkin Elmer FT–IR 1600 spectrometer, ¹H and ¹³C NMR spectra were measured on a Bruker Avance AV-500 spectrometer using (CH₃)₄Si as internal standard. The ESI mass spectrum was obtained using a ThermoFisher Scientific Orbitrap XL spectrometer. Crystals of the title compound suitable for X-ray structural analysis were taken from the crystallized product.

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SAINT-NT (Bruker, 2007); data reduction: SAINT-NT (Bruker, 2007); 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).

Figures top

	Fig. 1. Perspective view of the title compound including atom labeling and ring specification. Thermal ellipsoids for the non-hydrogen atoms are drawn at the 50% probability level. Broken lines represent hydrogen bonds.
	Fig. 2. Packing structure of the title compound showing hydrogen bond interactions as broken lines.

(E)-2-[2-(3-Nitrophenyl)ethenyl]quinolin-8-ol top

Crystal data top

C₁₇H₁₂N₂O₃	F(000) = 608
M_r = 292.29	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.1192P)² + 0.8405P] where P = (F_o² + 2F_c²)/3
2655 reflections	(Δ/σ)_max < 0.001
200 parameters	Δρ_max = 0.42 e Å⁻³
0 restraints	Δρ_min = −0.24 e Å⁻³

Crystal data top

C₁₇H₁₂N₂O₃	V = 1409.58 (8) Å³
M_r = 292.29	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 20.3346 (7) Å	µ = 0.10 mm⁻¹
b = 4.7167 (1) Å	T = 298 K
c = 15.5674 (6) Å	0.54 × 0.24 × 0.06 mm
β = 109.255 (2)°

Data collection top

Bruker X8 APEXII CCD detector diffractometer	2655 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2007)	1768 reflections with I > 2σ(I)
T_min = 0.950, T_max = 0.994	R_int = 0.028
22418 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.065	0 restraints
wR(F²) = 0.226	H-atom parameters constrained
S = 1.03	Δρ_max = 0.42 e Å⁻³
2655 reflections	Δρ_min = −0.24 e Å⁻³
200 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.

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 (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) x, −y+3/2, z−1/2; (ii) x, −y+1/2, z+1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	2.19	2.657 (3)	116.5
O1—H1···O2ⁱ	0.82	2.53	3.180 (5)	136.6
C10—H10···O1ⁱⁱ	0.93	2.51	3.400 (3)	160.0
C11—H11···N1	0.93	2.53	2.857 (4)	101.2

Symmetry codes: (i) x, −y+3/2, z−1/2; (ii) x, −y+1/2, z+1/2.

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Volume 69| Part 11| November 2013| Pages o1651-o1652

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