3-(3-Methyl­phen­yl)-5-(quinolin-8-yl­meth­oxy)-1,2,4-oxa­diazole monohydrate

Yang, L.; Liu, W.; Wang, H.; Chen, X.-W.; Wang, H.-B.

doi:10.1107/S160053681302477X

organic compounds

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ISSN: 2056-9890

Volume 69| Part 10| October 2013| Page o1541

doi:10.1107/S160053681302477X

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3-(3-Methylphenyl)-5-(quinolin-8-ylmethoxy)-1,2,4-oxadiazole monohydrate

Lu Yang,^a,^b Wei Liu,^a,^b Han Wang,^a,^b ^* Xing-Wei Chen ^a,^b and Hai-Bo Wang ^b

^aCollege of Science, Nanjing University of Technology, Xinmofan Road No.5 Nanjing, Nanjing 210009, People's Republic of China, and ^bCollege of Food Science and Light Industry, Nanjing University of Technology, Xinmofan Road No.5 Nanjing, Nanjing 210009, People's Republic of China
^*Correspondence e-mail: wanghaibo@njut.edu.cn

(Received 3 April 2013; accepted 5 September 2013; online 12 September 2013)

In the title compound, C₁₉H₁₅N₃O₂·H₂O, the oxadiazole ring and the quinoline unit are almost coplanar, making a dihedral angle of 7.66 (8)°. The dihedral angle between the benzene ring and the quinoline system is 25.95 (8)° while that between the benzene and the oxadiazole rings is 18.88 (9)°. The water molecule is hydrogen bonded to an oxadiazole N atom and to the quinoline N atom. In the crystal, these units are linked via C—H⋯O hydrogen bonds, forming two-dimensional networks lying parallel to the ab plane.

Related literature

For the preparation of the title compound, see: Chiou & Shine (1989 ). For the biological activity of 1,2,4-oxadiazole derivatives, see: Street et al. (1990 ). For metal complexes of related compounds, see: da Silva et al. (1999 ); Pibiri et al. (2010 ); Terenzi et al. (2011 ). For bond-length data, see: Allen et al. (1987 ).

Experimental

Crystal data

C₁₉H₁₅N₃O₂·H₂O
M_r = 335.36
Triclinic, $[P \overline 1]$
a = 7.2070 (14) Å
b = 7.6200 (15) Å
c = 15.109 (3) Å
α = 92.62 (3)°
β = 90.19 (3)°
γ = 92.15 (3)°
V = 828.3 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 293 K
0.30 × 0.10 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: ψ scan (North et al., 1968 ) T_min = 0.973, T_max = 0.991
3302 measured reflections
3039 independent reflections
1949 reflections with I > 2σ(I)
R_int = 0.015
3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F² > 2σ(F²)] = 0.054
wR(F²) = 0.162
S = 1.00
3039 reflections
233 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.18 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
OW—HWB⋯N2	0.91 (3)	2.09 (3)	2.980 (3)	169 (3)
OW—HWA⋯N1	0.94 (3)	1.91 (3)	2.830 (3)	165 (3)
C7—H7A⋯OWⁱ	0.93	2.51	3.272 (3)	139
C10—H10A⋯OWⁱⁱ	0.97	2.55	3.482 (3)	160
C10—H10B⋯OWⁱⁱⁱ	0.97	2.59	3.534 (3)	164
Symmetry codes: (i) -x-1, -y+1, -z+2; (ii) x+1, y, z; (iii) -x, -y+2, -z+2.

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994 ); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995 ); 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: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks D, I. DOI: 10.1107/S160053681302477X/im2428sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681302477X/im2428Isup2.hkl

checkCIF report

Comment top

1,2,4-Oxadiazole derivatives have shown high biological activity, such as antibacterial, anti-HIV and weed control (Street et al., 1990). They are therefore widely used in medicinal chemistry and as pesticides. 1,2,4-Oxadiazole derivatives in combination with metal ions can also be used in fluorescent recognition (da Silva et al., 1999; Pibiri et al., 2010; Terenzi et al., 2011). The title compound 5-(quinoline-8-ylmethoxy)-3-p-tolyl-1,2,4-oxadiazole was also used in metal ions fluorescent recognition. In the molecule of 5-(quinoline-8-ylmethoxy)-3-p-tolyl-1,2,4-oxadiazole hydrate (Fig. 1) bond lengths (Allen et al., 1987) and angles are within normal ranges.The oxadiazol ring and the quinoline moiety are almost coplanar showing a dihedral angle of 7.66 (8)°. The dihedral angles between the benzene ring and the quinoline system is 25.95 (8)°, the corresponding angle between the benzene and the oxadiazol rings is 18.88 (9)°. The crystal structure is established by intermolecular N—H···O and O—H···O hydrogen bonds (Fig. 2).

Related literature top

For the preparation of the title compound, see: Chiou & Shine (1989). For the biological activity of 1,2,4-oxadiazole derivatives, see: Street et al. (1990). For metal complexes of related compounds, see: da Silva et al. (1999); Pibiri et al. (2010); Terenzi et al. (2011). For bond-length data, see: Allen et al. (1987).

Experimental top

5-(Quinoline-8-ylmethoxy)-3-p-tolyl-1,2,4-oxadiazole was prepared by a literature method (Chiou & Shine, 1989). 3-(4-Methyl-phenyl)-5-chloromethyl-1,2,4-oxadizole (3.4 g, 16.4 mmol), 8-hydroxy-quinoline (2.4 g, 16.4 mmol), potassium carbonate (3.4 g ,24.6 mmol) and potassium iodide (catalytic amount) were added to acetone (40 ml). The mixture was then heated to reflux for 6 hours. After being cooled to room temperature, the mixture was filtered and evaporated to afford the product as a yellow solid. The crude product was re-crystallized from ethyl acetate (yield 3.1g, 59.8%). Crystals suitable for X-ray analysis were obtained by slow evaporation of an ethyl acetate solution.

Computing details top

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS (Enraf–Nonius, 1994); data reduction: XCAD4 (Harms & Wocadlo, 1995); 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: publCIF (Westrip, 2010).

Figures top

	Fig. 1. Molecular structure of the title molecule with displacement ellipsoids drawn at the 50% probability level.
	Fig. 2. Packing diagram of the title compound. Hydrogen bonds are shown as dashed lines.

3-(3-Methylphenyl)-5-(quinolin-8-ylmethoxy)-1,2,4-oxadiazole monohydrate top

Crystal data top

C₁₉H₁₅N₃O₂·H₂O	Z = 2
M_r = 335.36	F(000) = 352
Triclinic, P1	D_x = 1.345 Mg m⁻³
Hall symbol: -P 1	Melting point: 342 K
a = 7.2070 (14) Å	Mo Kα radiation, λ = 0.71073 Å
b = 7.6200 (15) Å	Cell parameters from 25 reflections
c = 15.109 (3) Å	θ = 9–13°
α = 92.62 (3)°	µ = 0.09 mm⁻¹
β = 90.19 (3)°	T = 293 K
γ = 92.15 (3)°	Block, yellow
V = 828.3 (3) Å³	0.30 × 0.10 × 0.10 mm

Data collection top

Enraf–Nonius CAD-4 diffractometer	1949 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.015
Graphite monochromator	θ_max = 25.4°, θ_min = 1.4°
ω/2θ scans	h = 0→8
Absorption correction: ψ scan (North et al., 1968)	k = −9→9
T_min = 0.973, T_max = 0.991	l = −18→18
3302 measured reflections	3 standard reflections every 200 reflections
3039 independent reflections	intensity decay: 1%

Refinement top

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)] = 0.054	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.162	w = 1/[σ²(F_o²) + (0.097P)²] where P = (F_o² + 2F_c²)/3
S = 1.00	(Δ/σ)_max < 0.001
3039 reflections	Δρ_max = 0.24 e Å⁻³
233 parameters	Δρ_min = −0.18 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.033 (7)

Crystal data top

C₁₉H₁₅N₃O₂·H₂O	γ = 92.15 (3)°
M_r = 335.36	V = 828.3 (3) Å³
Triclinic, P1	Z = 2
a = 7.2070 (14) Å	Mo Kα radiation
b = 7.6200 (15) Å	µ = 0.09 mm⁻¹
c = 15.109 (3) Å	T = 293 K
α = 92.62 (3)°	0.30 × 0.10 × 0.10 mm
β = 90.19 (3)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	1949 reflections with I > 2σ(I)
Absorption correction: ψ scan (North et al., 1968)	R_int = 0.015
T_min = 0.973, T_max = 0.991	3 standard reflections every 200 reflections
3302 measured reflections	intensity decay: 1%
3039 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.054	0 restraints
wR(F²) = 0.162	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	Δρ_max = 0.24 e Å⁻³
3039 reflections	Δρ_min = −0.18 e Å⁻³
233 parameters

Special details top

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 > 2sigma(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	0.0819 (2)	0.7951 (2)	0.99656 (11)	0.0571 (5)
N1	−0.1889 (3)	0.6301 (2)	1.08273 (13)	0.0522 (5)
C1	0.2813 (3)	0.8077 (3)	1.12657 (18)	0.0596 (7)
H1B	0.3763	0.8670	1.0974	0.071*
N2	0.0057 (3)	0.8438 (2)	0.81930 (13)	0.0511 (5)
O2	0.2873 (2)	0.9553 (2)	0.80096 (12)	0.0695 (6)
C2	0.3046 (4)	0.7675 (4)	1.21478 (19)	0.0667 (7)
H2B	0.4155	0.8005	1.2437	0.080*
C3	0.1700 (4)	0.6819 (4)	1.25913 (18)	0.0656 (7)
H3A	0.1894	0.6553	1.3178	0.079*
N3	0.2016 (3)	0.9460 (3)	0.71676 (15)	0.0714 (7)
C4	−0.0008 (3)	0.6320 (3)	1.21701 (17)	0.0551 (6)
C5	−0.1489 (4)	0.5465 (3)	1.25918 (18)	0.0642 (7)
H5A	−0.1374	0.5179	1.3181	0.077*
C6	−0.3092 (4)	0.5051 (3)	1.21418 (19)	0.0653 (7)
H6A	−0.4084	0.4483	1.2416	0.078*
C7	−0.3218 (3)	0.5497 (3)	1.12629 (18)	0.0594 (7)
H7A	−0.4323	0.5206	1.0962	0.071*
C8	−0.0273 (3)	0.6721 (3)	1.12723 (16)	0.0475 (6)
C9	0.1196 (3)	0.7605 (3)	1.08256 (16)	0.0486 (6)
C10	0.2240 (3)	0.8842 (3)	0.94993 (17)	0.0557 (6)
H10A	0.3386	0.8219	0.9528	0.067*
H10B	0.2460	1.0022	0.9757	0.067*
C11	0.1608 (3)	0.8911 (3)	0.85698 (17)	0.0511 (6)
C12	0.0369 (3)	0.8783 (3)	0.73185 (16)	0.0535 (6)
C13	−0.0981 (3)	0.8373 (3)	0.66076 (16)	0.0553 (6)
C14	−0.2843 (4)	0.8113 (3)	0.67896 (17)	0.0617 (7)
H14A	−0.3249	0.8161	0.7374	0.074*
C15	−0.4105 (4)	0.7784 (4)	0.61087 (18)	0.0687 (7)
H15A	−0.5356	0.7628	0.6245	0.082*
C16	−0.3573 (4)	0.7677 (3)	0.52325 (17)	0.0677 (8)
C17	−0.1699 (5)	0.7904 (4)	0.50615 (19)	0.0847 (9)
H17A	−0.1291	0.7826	0.4478	0.102*
C18	−0.0424 (4)	0.8242 (4)	0.57307 (19)	0.0814 (9)
H18A	0.0828	0.8385	0.5594	0.098*
C19	−0.4974 (5)	0.7358 (4)	0.45006 (19)	0.0905 (10)
H19A	−0.4352	0.7339	0.3940	0.136*
H19B	−0.5845	0.8282	0.4523	0.136*
H19C	−0.5622	0.6250	0.4571	0.136*
OW	−0.3313 (2)	0.7299 (3)	0.91840 (14)	0.0733 (6)
HWB	−0.236 (5)	0.757 (4)	0.8819 (19)	0.088*
HWA	−0.274 (4)	0.682 (4)	0.967 (2)	0.088*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0383 (8)	0.0683 (11)	0.0639 (11)	−0.0106 (8)	−0.0065 (8)	0.0075 (8)
N1	0.0400 (10)	0.0500 (11)	0.0661 (13)	−0.0038 (9)	−0.0033 (10)	0.0013 (9)
C1	0.0387 (13)	0.0624 (16)	0.0769 (19)	0.0010 (11)	−0.0102 (12)	−0.0030 (13)
N2	0.0425 (11)	0.0550 (12)	0.0551 (12)	−0.0019 (9)	0.0074 (9)	−0.0021 (9)
O2	0.0450 (10)	0.0884 (13)	0.0744 (13)	−0.0133 (9)	0.0078 (9)	0.0081 (10)
C2	0.0498 (15)	0.0751 (18)	0.0742 (19)	0.0041 (13)	−0.0197 (14)	−0.0088 (14)
C3	0.0634 (17)	0.0752 (18)	0.0579 (16)	0.0075 (14)	−0.0165 (14)	−0.0034 (13)
N3	0.0556 (13)	0.0913 (17)	0.0670 (15)	−0.0103 (12)	0.0084 (12)	0.0106 (12)
C4	0.0528 (14)	0.0486 (13)	0.0640 (16)	0.0094 (11)	−0.0032 (12)	−0.0022 (11)
C5	0.0694 (18)	0.0598 (16)	0.0643 (17)	0.0119 (14)	0.0029 (14)	0.0052 (13)
C6	0.0580 (16)	0.0608 (16)	0.0773 (19)	−0.0011 (13)	0.0091 (14)	0.0079 (14)
C7	0.0457 (14)	0.0567 (15)	0.0753 (18)	−0.0028 (12)	−0.0016 (13)	0.0017 (13)
C8	0.0405 (12)	0.0420 (12)	0.0595 (15)	0.0032 (10)	−0.0053 (11)	−0.0046 (10)
C9	0.0370 (12)	0.0478 (13)	0.0607 (15)	0.0047 (10)	−0.0081 (11)	−0.0021 (11)
C10	0.0327 (11)	0.0617 (15)	0.0713 (17)	−0.0062 (11)	0.0050 (11)	−0.0053 (12)
C11	0.0351 (12)	0.0505 (13)	0.0668 (16)	−0.0005 (10)	0.0058 (11)	−0.0041 (11)
C12	0.0478 (13)	0.0534 (14)	0.0592 (16)	0.0016 (11)	0.0118 (11)	0.0019 (11)
C13	0.0573 (15)	0.0544 (14)	0.0540 (15)	0.0009 (12)	0.0074 (12)	0.0002 (11)
C14	0.0577 (15)	0.0757 (17)	0.0516 (15)	0.0001 (13)	0.0060 (12)	0.0021 (12)
C15	0.0590 (15)	0.0846 (19)	0.0623 (18)	−0.0007 (14)	−0.0003 (13)	0.0034 (14)
C16	0.085 (2)	0.0642 (17)	0.0536 (17)	0.0042 (15)	−0.0039 (14)	0.0020 (13)
C17	0.090 (2)	0.112 (3)	0.0512 (17)	−0.0007 (19)	0.0109 (16)	−0.0037 (16)
C18	0.0700 (18)	0.111 (2)	0.0616 (18)	−0.0049 (17)	0.0182 (16)	−0.0037 (16)
C19	0.111 (3)	0.100 (2)	0.0606 (18)	0.003 (2)	−0.0170 (18)	0.0006 (17)
OW	0.0446 (10)	0.1012 (15)	0.0735 (13)	−0.0152 (10)	−0.0081 (9)	0.0147 (11)

Geometric parameters (Å, º) top

O1—C9	1.366 (3)	C7—H7A	0.9300
O1—C10	1.415 (3)	C8—C9	1.422 (3)
N1—C7	1.313 (3)	C10—C11	1.479 (4)
N1—C8	1.363 (3)	C10—H10A	0.9700
C1—C9	1.368 (3)	C10—H10B	0.9700
C1—C2	1.392 (4)	C12—C13	1.462 (3)
C1—H1B	0.9300	C13—C14	1.380 (4)
N2—C11	1.285 (3)	C13—C18	1.386 (4)
N2—C12	1.376 (3)	C14—C15	1.379 (4)
O2—C11	1.340 (3)	C14—H14A	0.9300
O2—N3	1.410 (3)	C15—C16	1.379 (4)
C2—C3	1.346 (4)	C15—H15A	0.9300
C2—H2B	0.9300	C16—C17	1.381 (4)
C3—C4	1.415 (3)	C16—C19	1.501 (4)
C3—H3A	0.9300	C17—C18	1.373 (4)
N3—C12	1.301 (3)	C17—H17A	0.9300
C4—C5	1.400 (4)	C18—H18A	0.9300
C4—C8	1.418 (3)	C19—H19A	0.9600
C5—C6	1.358 (4)	C19—H19B	0.9600
C5—H5A	0.9300	C19—H19C	0.9600
C6—C7	1.389 (4)	OW—HWB	0.91 (3)
C6—H6A	0.9300	OW—HWA	0.94 (3)

C9—O1—C10	116.60 (18)	O1—C10—H10B	110.3
C7—N1—C8	117.4 (2)	C11—C10—H10B	110.3
C9—C1—C2	120.5 (2)	H10A—C10—H10B	108.5
C9—C1—H1B	119.8	N2—C11—O2	113.4 (2)
C2—C1—H1B	119.8	N2—C11—C10	131.4 (2)
C11—N2—C12	103.1 (2)	O2—C11—C10	115.16 (19)
C11—O2—N3	105.97 (17)	N3—C12—N2	114.0 (2)
C3—C2—C1	121.4 (2)	N3—C12—C13	122.2 (2)
C3—C2—H2B	119.3	N2—C12—C13	123.9 (2)
C1—C2—H2B	119.3	C14—C13—C18	118.2 (3)
C2—C3—C4	120.4 (3)	C14—C13—C12	121.0 (2)
C2—C3—H3A	119.8	C18—C13—C12	120.8 (2)
C4—C3—H3A	119.8	C15—C14—C13	120.2 (2)
C12—N3—O2	103.59 (19)	C15—C14—H14A	119.9
C5—C4—C3	123.8 (3)	C13—C14—H14A	119.9
C5—C4—C8	117.1 (2)	C14—C15—C16	122.2 (3)
C3—C4—C8	119.0 (2)	C14—C15—H15A	118.9
C6—C5—C4	120.1 (3)	C16—C15—H15A	118.9
C6—C5—H5A	120.0	C15—C16—C17	116.9 (3)
C4—C5—H5A	120.0	C15—C16—C19	121.3 (3)
C5—C6—C7	118.5 (3)	C17—C16—C19	121.8 (3)
C5—C6—H6A	120.7	C18—C17—C16	121.7 (3)
C7—C6—H6A	120.7	C18—C17—H17A	119.2
N1—C7—C6	124.6 (2)	C16—C17—H17A	119.2
N1—C7—H7A	117.7	C17—C18—C13	120.8 (3)
C6—C7—H7A	117.7	C17—C18—H18A	119.6
N1—C8—C4	122.3 (2)	C13—C18—H18A	119.6
N1—C8—C9	119.1 (2)	C16—C19—H19A	109.5
C4—C8—C9	118.7 (2)	C16—C19—H19B	109.5
O1—C9—C1	125.1 (2)	H19A—C19—H19B	109.5
O1—C9—C8	114.81 (19)	C16—C19—H19C	109.5
C1—C9—C8	120.1 (2)	H19A—C19—H19C	109.5
O1—C10—C11	107.17 (18)	H19B—C19—H19C	109.5
O1—C10—H10A	110.3	HWB—OW—HWA	104 (3)
C11—C10—H10A	110.3

C9—C1—C2—C3	0.0 (4)	C12—N2—C11—O2	0.9 (3)
C1—C2—C3—C4	−0.8 (4)	C12—N2—C11—C10	−177.9 (2)
C11—O2—N3—C12	−0.1 (3)	N3—O2—C11—N2	−0.5 (3)
C2—C3—C4—C5	−178.5 (2)	N3—O2—C11—C10	178.5 (2)
C2—C3—C4—C8	0.6 (4)	O1—C10—C11—N2	5.4 (4)
C3—C4—C5—C6	179.2 (2)	O1—C10—C11—O2	−173.34 (19)
C8—C4—C5—C6	0.1 (4)	O2—N3—C12—N2	0.7 (3)
C4—C5—C6—C7	0.0 (4)	O2—N3—C12—C13	−177.1 (2)
C8—N1—C7—C6	0.1 (4)	C11—N2—C12—N3	−1.0 (3)
C5—C6—C7—N1	−0.1 (4)	C11—N2—C12—C13	176.7 (2)
C7—N1—C8—C4	0.0 (3)	N3—C12—C13—C14	−162.3 (3)
C7—N1—C8—C9	−179.5 (2)	N2—C12—C13—C14	20.1 (4)
C5—C4—C8—N1	−0.1 (3)	N3—C12—C13—C18	17.4 (4)
C3—C4—C8—N1	−179.2 (2)	N2—C12—C13—C18	−160.1 (3)
C5—C4—C8—C9	179.4 (2)	C18—C13—C14—C15	−1.8 (4)
C3—C4—C8—C9	0.3 (3)	C12—C13—C14—C15	177.9 (2)
C10—O1—C9—C1	1.1 (3)	C13—C14—C15—C16	0.9 (4)
C10—O1—C9—C8	179.53 (19)	C14—C15—C16—C17	0.4 (4)
C2—C1—C9—O1	179.3 (2)	C14—C15—C16—C19	−178.6 (3)
C2—C1—C9—C8	0.9 (4)	C15—C16—C17—C18	−0.7 (5)
N1—C8—C9—O1	0.0 (3)	C19—C16—C17—C18	178.2 (3)
C4—C8—C9—O1	−179.54 (19)	C16—C17—C18—C13	−0.2 (5)
N1—C8—C9—C1	178.5 (2)	C14—C13—C18—C17	1.5 (5)
C4—C8—C9—C1	−1.1 (3)	C12—C13—C18—C17	−178.2 (3)
C9—O1—C10—C11	174.34 (18)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
OW—HWB···N2	0.91 (3)	2.09 (3)	2.980 (3)	169 (3)
OW—HWA···N1	0.94 (3)	1.91 (3)	2.830 (3)	165 (3)
C7—H7A···OWⁱ	0.93	2.51	3.272 (3)	139
C10—H10A···OWⁱⁱ	0.97	2.55	3.482 (3)	160
C10—H10B···OWⁱⁱⁱ	0.97	2.59	3.534 (3)	164

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
OW—HWB···N2	0.91 (3)	2.09 (3)	2.980 (3)	169 (3)
OW—HWA···N1	0.94 (3)	1.91 (3)	2.830 (3)	165 (3)
C7—H7A···OWⁱ	0.9300	2.5100	3.272 (3)	139.00
C10—H10A···OWⁱⁱ	0.9700	2.5500	3.482 (3)	160.00
C10—H10B···OWⁱⁱⁱ	0.9700	2.5900	3.534 (3)	164.00

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

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