8-[(3-Phenyl-1,2,4-oxa­diazol-5-yl)meth­oxy]quinoline monohydrate

Bai, S.-Y.; Shen, H.; Han, X.-Y.; Lv, L.-J.; Wang, H.-B.

doi:10.1107/S1600536813014529

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 69| Part 7| July 2013| Page o1034

https://doi.org/10.1107/S1600536813014529

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8-[(3-Phenyl-1,2,4-oxadiazol-5-yl)methoxy]quinoline monohydrate

Shu-Yuan Bai,^a,^b Hong Shen,^a,^b Xin-Yi Han,^a Ling-Jie Lv ^a,^b and Hai-Bo Wang ^a ^*

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

(Received 17 May 2013; accepted 27 May 2013; online 8 June 2013)

In the title compound, C₁₈H₁₃N₃O₂·H₂O, the oxadiazole ring forms dihedral angles 7.21 (10) and 21.25 (11)° with the quinoline and benzene rings, respectively. The crystal structure features O—H⋯N hydrogen bonds and is further consolidated by C—H⋯O hydrogen-bonding interactions involving the water molecule of hydration.

Related literature

For general background, see: Katritzky et al. (1992 ). For preparation of the title compound, see: Shishue & Henry (1989 ). For crystal structure of a related compound, see: Liu et al. (2006 ).

Experimental

Crystal data

C₁₈H₁₃N₃O₂·H₂O
M_r = 321.33
Monoclinic, P 2₁ /n
a = 7.0430 (14) Å
b = 7.5800 (15) Å
c = 29.114 (6) Å
β = 95.33 (3)°
V = 1547.6 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 293 K
0.30 × 0.20 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: ψ scan (North et al., 1968 ) T_min = 0.972, T_max = 0.990
3101 measured reflections
2853 independent reflections
1608 reflections with I > 2σ(I)
R_int = 0.025
3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F² > 2σ(F²)] = 0.052
wR(F²) = 0.144
S = 0.95
2853 reflections
223 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.15 e Å⁻³
Δρ_min = −0.15 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1W⋯N2	0.79 (4)	2.20 (4)	2.988 (3)	171 (4)
O1W—H2W⋯N3	0.81 (4)	2.00 (4)	2.810 (3)	174 (4)
C9—H9A⋯O1Wⁱ	0.97	2.54	3.437 (3)	154
C12—H12A⋯O1Wⁱⁱ	0.93	2.51	3.268 (4)	139
Symmetry codes: (i) x-1, y, z; (ii) -x+2, -y+2, -z+1.

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: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536813014529/pv2633sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536813014529/pv2633Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536813014529/pv2633Isup3.cml

checkCIF report

Comment top

Due to unique biological activity in medicine and pesticide, 1,2,4-oxadiazole derivatives have received an increased attention. It plays an increasingly important role in pharmaceutical synthesis, if different heterocyclics were introduced into 1,2,4-oxadiazole ring (Katritzky et al., 1992). We have synthesized the title compound which is a novel derivative of 1,2,4-oxadiazole. In this article, we describe the synthesis and crystal structure of the title compound.

In the title molecule (Fig. 1) the bond distances and bond angles agree very well with the corresponding bond distances and angles reported in a closely related compound (Liu et al., 2006). The quinoline ring is essentially planar (rmsd = 0.0118 Å). The oxadiazole ring forms dihedral angles 7.21 (10) and 21.25 (11)° with the quinoline and benzene rings, respectively. The crystal structure is stabilized by O—H···N hydrogen bonds and further consolidated by C—H···O hydrogen bonding interactions involving the water of hydration (Fig. 2 & Tab. 1).

Related literature top

For general background, see: Katritzky et al. (1992). For preparation of the title compound, see: Shishue & Henry (1989). For crystal structure of a related compound, see: Liu et al. (2006).

Experimental top

To a flask charged with 30 mL of acetone were added 3-phenyl-5-chloromethyl-1,2,4-oxadiazole (1.95 g, 10 mmol), 8-hydroxy quinoline (1.45 g, 10 mmol), potassium carbonate (2.0 g, 15 mmol), and a catalytic amount of potassium iodide. The reaction mixture was stirred at refluxing condition for about 5 h. After being cooled to room temperature, the mixture was filtered and evaporated in vacuo. The crude product was further recrystallized from ethyl acetate to give white solid (yield = 2.26 g; 75%). Crystals suitable for X-ray crystallographic studies were grown by slow evaporation of ethyl acetate solution.

Structure description top

For general background, see: Katritzky et al. (1992). For preparation of the title compound, see: Shishue & Henry (1989). For crystal structure of a related compound, see: Liu et al. (2006).

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: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. A packing diagram of the title compound viewed down the c axis. Dashed lines indicate intermolecular O—H···N and C—H···O interactions.

8-[(3-Phenyl-1,2,4-oxadiazol-5-yl)methoxy]quinoline monohydrate top

Crystal data top

C₁₈H₁₃N₃O₂·H₂O	F(000) = 672
M_r = 321.33	D_x = 1.379 Mg m⁻³
Monoclinic, P2₁/n	Melting point: 438 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 7.0430 (14) Å	Cell parameters from 25 reflections
b = 7.5800 (15) Å	θ = 9–13°
c = 29.114 (6) Å	µ = 0.10 mm⁻¹
β = 95.33 (3)°	T = 293 K
V = 1547.6 (5) Å³	Block, colourless
Z = 4	0.30 × 0.20 × 0.10 mm

Data collection top

Enraf–Nonius CAD-4 diffractometer	1608 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.025
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 = 0→9
T_min = 0.972, T_max = 0.990	l = −35→34
3101 measured reflections	3 standard reflections every 200 reflections
2853 independent reflections	intensity decay: 1%

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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.144	H atoms treated by a mixture of independent and constrained refinement
S = 0.95	w = 1/[σ²(F_o²) + (0.070P)²] where P = (F_o² + 2F_c²)/3
2853 reflections	(Δ/σ)_max < 0.001
223 parameters	Δρ_max = 0.15 e Å⁻³
0 restraints	Δρ_min = −0.15 e Å⁻³

Crystal data top

C₁₈H₁₃N₃O₂·H₂O	V = 1547.6 (5) Å³
M_r = 321.33	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 7.0430 (14) Å	µ = 0.10 mm⁻¹
b = 7.5800 (15) Å	T = 293 K
c = 29.114 (6) Å	0.30 × 0.20 × 0.10 mm
β = 95.33 (3)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	1608 reflections with I > 2σ(I)
Absorption correction: ψ scan (North et al., 1968)	R_int = 0.025
T_min = 0.972, T_max = 0.990	3 standard reflections every 200 reflections
3101 measured reflections	intensity decay: 1%
2853 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.052	0 restraints
wR(F²) = 0.144	H atoms treated by a mixture of independent and constrained refinement
S = 0.95	Δρ_max = 0.15 e Å⁻³
2853 reflections	Δρ_min = −0.15 e Å⁻³
223 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	0.1455 (2)	0.5455 (3)	0.39671 (7)	0.0669 (6)
O2	0.4113 (2)	0.7022 (2)	0.49830 (6)	0.0521 (5)
N1	0.2012 (3)	0.5612 (3)	0.35162 (8)	0.0684 (7)
N2	0.4312 (3)	0.6622 (3)	0.40388 (7)	0.0484 (6)
N3	0.7080 (3)	0.8663 (3)	0.54211 (7)	0.0501 (6)
C1	0.3907 (5)	0.7139 (5)	0.27655 (11)	0.0791 (10)
H1B	0.2625	0.6855	0.2702	0.095*
C2	0.4931 (7)	0.7816 (5)	0.24221 (11)	0.0948 (12)
H2B	0.4325	0.8006	0.2129	0.114*
C3	0.6821 (6)	0.8209 (5)	0.25099 (12)	0.0874 (11)
H3B	0.7491	0.8687	0.2279	0.105*
C4	0.7724 (5)	0.7900 (5)	0.29354 (11)	0.0843 (11)
H4A	0.9022	0.8128	0.2991	0.101*
C5	0.6733 (4)	0.7253 (4)	0.32851 (10)	0.0694 (9)
H5A	0.7360	0.7061	0.3576	0.083*
C6	0.4811 (4)	0.6888 (3)	0.32043 (9)	0.0550 (7)
C7	0.3704 (4)	0.6317 (4)	0.35832 (9)	0.0518 (7)
C8	0.2890 (3)	0.6098 (3)	0.42497 (9)	0.0478 (7)
C9	0.2552 (3)	0.6131 (4)	0.47439 (9)	0.0507 (7)
H9A	0.1371	0.6743	0.4785	0.061*
H9B	0.2462	0.4937	0.4860	0.061*
C10	0.4014 (3)	0.7312 (3)	0.54418 (9)	0.0446 (6)
C11	0.5607 (3)	0.8199 (3)	0.56692 (9)	0.0436 (6)
C12	0.8557 (4)	0.9462 (4)	0.56418 (10)	0.0587 (8)
H12A	0.9559	0.9794	0.5474	0.070*
C13	0.8705 (4)	0.9839 (4)	0.61116 (11)	0.0652 (8)
H13A	0.9782	1.0402	0.6251	0.078*
C14	0.7261 (4)	0.9374 (4)	0.63636 (10)	0.0639 (8)
H14A	0.7340	0.9610	0.6678	0.077*
C15	0.5641 (4)	0.8531 (3)	0.61456 (9)	0.0496 (7)
C16	0.4096 (4)	0.7993 (4)	0.63873 (10)	0.0627 (8)
H16A	0.4103	0.8221	0.6701	0.075*
C17	0.2598 (4)	0.7139 (4)	0.61586 (10)	0.0627 (8)
H17A	0.1585	0.6781	0.6320	0.075*
C18	0.2546 (4)	0.6787 (3)	0.56860 (10)	0.0527 (7)
H18A	0.1508	0.6194	0.5537	0.063*
O1W	0.8011 (3)	0.7785 (4)	0.45314 (8)	0.0770 (7)
H1W	0.709 (6)	0.747 (5)	0.4376 (13)	0.116*
H2W	0.770 (5)	0.810 (5)	0.4781 (14)	0.116*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0498 (11)	0.0858 (15)	0.0641 (13)	−0.0154 (11)	−0.0007 (10)	−0.0105 (11)
O2	0.0398 (9)	0.0638 (12)	0.0531 (11)	−0.0111 (9)	0.0062 (8)	−0.0030 (9)
N1	0.0558 (15)	0.0858 (19)	0.0621 (17)	−0.0069 (14)	−0.0027 (12)	−0.0117 (14)
N2	0.0456 (12)	0.0520 (14)	0.0465 (13)	−0.0002 (11)	−0.0010 (10)	0.0055 (10)
N3	0.0407 (12)	0.0477 (13)	0.0628 (15)	−0.0052 (11)	0.0094 (11)	−0.0013 (11)
C1	0.084 (2)	0.095 (3)	0.055 (2)	0.007 (2)	−0.0086 (18)	−0.0022 (18)
C2	0.136 (4)	0.100 (3)	0.047 (2)	0.013 (3)	0.000 (2)	0.0069 (19)
C3	0.125 (3)	0.083 (3)	0.058 (2)	−0.009 (2)	0.025 (2)	−0.0040 (19)
C4	0.093 (2)	0.103 (3)	0.060 (2)	−0.021 (2)	0.0226 (19)	−0.008 (2)
C5	0.072 (2)	0.086 (2)	0.0511 (18)	−0.0084 (18)	0.0096 (15)	−0.0025 (16)
C6	0.0674 (18)	0.0506 (17)	0.0458 (16)	0.0046 (15)	−0.0015 (14)	−0.0047 (13)
C7	0.0496 (16)	0.0559 (17)	0.0480 (17)	0.0047 (14)	−0.0057 (13)	−0.0052 (13)
C8	0.0388 (14)	0.0489 (16)	0.0543 (17)	0.0007 (13)	−0.0035 (13)	0.0024 (13)
C9	0.0319 (13)	0.0548 (17)	0.0644 (18)	−0.0057 (13)	−0.0010 (12)	0.0031 (14)
C10	0.0417 (14)	0.0441 (15)	0.0484 (15)	0.0021 (12)	0.0070 (12)	0.0027 (12)
C11	0.0392 (14)	0.0393 (14)	0.0530 (16)	0.0044 (12)	0.0075 (12)	0.0026 (12)
C12	0.0444 (16)	0.0544 (18)	0.077 (2)	−0.0062 (14)	0.0029 (14)	−0.0024 (16)
C13	0.0529 (17)	0.064 (2)	0.075 (2)	0.0011 (16)	−0.0135 (16)	−0.0144 (17)
C14	0.0683 (19)	0.063 (2)	0.0590 (18)	0.0127 (17)	−0.0046 (16)	−0.0103 (16)
C15	0.0479 (15)	0.0474 (16)	0.0530 (17)	0.0067 (13)	0.0016 (13)	−0.0006 (13)
C16	0.071 (2)	0.070 (2)	0.0493 (16)	0.0152 (17)	0.0170 (15)	0.0014 (15)
C17	0.0569 (18)	0.071 (2)	0.063 (2)	0.0039 (16)	0.0227 (15)	0.0065 (16)
C18	0.0430 (14)	0.0549 (17)	0.0615 (18)	−0.0011 (13)	0.0124 (13)	0.0059 (14)
O1W	0.0487 (12)	0.1114 (19)	0.0729 (16)	−0.0250 (13)	0.0159 (11)	−0.0162 (14)

Geometric parameters (Å, º) top

O1—C8	1.335 (3)	C8—C9	1.480 (3)
O1—N1	1.410 (3)	C9—H9A	0.9700
O2—C10	1.362 (3)	C9—H9B	0.9700
O2—C9	1.417 (3)	C10—C18	1.367 (3)
N1—C7	1.304 (3)	C10—C11	1.418 (3)
N2—C8	1.285 (3)	C11—C15	1.408 (3)
N2—C7	1.375 (3)	C12—C13	1.392 (4)
N3—C12	1.318 (3)	C12—H12A	0.9300
N3—C11	1.364 (3)	C13—C14	1.355 (4)
C1—C2	1.385 (5)	C13—H13A	0.9300
C1—C6	1.387 (4)	C14—C15	1.406 (4)
C1—H1B	0.9300	C14—H14A	0.9300
C2—C3	1.365 (5)	C15—C16	1.410 (4)
C2—H2B	0.9300	C16—C17	1.358 (4)
C3—C4	1.359 (5)	C16—H16A	0.9300
C3—H3B	0.9300	C17—C18	1.399 (4)
C4—C5	1.377 (4)	C17—H17A	0.9300
C4—H4A	0.9300	C18—H18A	0.9300
C5—C6	1.380 (4)	O1W—H1W	0.79 (4)
C5—H5A	0.9300	O1W—H2W	0.81 (4)
C6—C7	1.473 (4)

C8—O1—N1	106.44 (19)	O2—C9—H9B	110.2
C10—O2—C9	116.82 (19)	C8—C9—H9B	110.2
C7—N1—O1	103.0 (2)	H9A—C9—H9B	108.5
C8—N2—C7	102.9 (2)	O2—C10—C18	125.0 (2)
C12—N3—C11	117.7 (2)	O2—C10—C11	115.1 (2)
C2—C1—C6	119.4 (3)	C18—C10—C11	119.9 (3)
C2—C1—H1B	120.3	N3—C11—C15	122.1 (2)
C6—C1—H1B	120.3	N3—C11—C10	118.9 (2)
C3—C2—C1	120.7 (3)	C15—C11—C10	119.0 (2)
C3—C2—H2B	119.7	N3—C12—C13	123.8 (3)
C1—C2—H2B	119.7	N3—C12—H12A	118.1
C4—C3—C2	119.9 (4)	C13—C12—H12A	118.1
C4—C3—H3B	120.0	C14—C13—C12	119.2 (3)
C2—C3—H3B	120.0	C14—C13—H13A	120.4
C3—C4—C5	120.6 (4)	C12—C13—H13A	120.4
C3—C4—H4A	119.7	C13—C14—C15	119.5 (3)
C5—C4—H4A	119.7	C13—C14—H14A	120.3
C4—C5—C6	120.1 (3)	C15—C14—H14A	120.3
C4—C5—H5A	119.9	C14—C15—C11	117.7 (3)
C6—C5—H5A	119.9	C14—C15—C16	122.5 (3)
C5—C6—C1	119.2 (3)	C11—C15—C16	119.8 (3)
C5—C6—C7	120.7 (2)	C17—C16—C15	119.6 (3)
C1—C6—C7	120.0 (3)	C17—C16—H16A	120.2
N1—C7—N2	114.3 (3)	C15—C16—H16A	120.2
N1—C7—C6	123.2 (2)	C16—C17—C18	121.4 (3)
N2—C7—C6	122.3 (2)	C16—C17—H17A	119.3
N2—C8—O1	113.4 (2)	C18—C17—H17A	119.3
N2—C8—C9	131.5 (2)	C10—C18—C17	120.3 (3)
O1—C8—C9	115.1 (2)	C10—C18—H18A	119.9
O2—C9—C8	107.3 (2)	C17—C18—H18A	119.9
O2—C9—H9A	110.2	H1W—O1W—H2W	109 (4)
C8—C9—H9A	110.2

C8—O1—N1—C7	0.3 (3)	C9—O2—C10—C18	1.0 (4)
C6—C1—C2—C3	1.1 (6)	C9—O2—C10—C11	179.7 (2)
C1—C2—C3—C4	1.4 (6)	C12—N3—C11—C15	−0.6 (4)
C2—C3—C4—C5	−2.4 (6)	C12—N3—C11—C10	−179.0 (2)
C3—C4—C5—C6	0.9 (5)	O2—C10—C11—N3	−0.7 (3)
C4—C5—C6—C1	1.6 (5)	C18—C10—C11—N3	178.1 (2)
C4—C5—C6—C7	−175.6 (3)	O2—C10—C11—C15	−179.1 (2)
C2—C1—C6—C5	−2.6 (5)	C18—C10—C11—C15	−0.3 (4)
C2—C1—C6—C7	174.6 (3)	C11—N3—C12—C13	0.7 (4)
O1—N1—C7—N2	0.6 (3)	N3—C12—C13—C14	−0.2 (4)
O1—N1—C7—C6	−174.3 (2)	C12—C13—C14—C15	−0.3 (4)
C8—N2—C7—N1	−1.2 (3)	C13—C14—C15—C11	0.4 (4)
C8—N2—C7—C6	173.7 (2)	C13—C14—C15—C16	179.2 (3)
C5—C6—C7—N1	−165.4 (3)	N3—C11—C15—C14	0.1 (4)
C1—C6—C7—N1	17.5 (4)	C10—C11—C15—C14	178.4 (2)
C5—C6—C7—N2	20.2 (4)	N3—C11—C15—C16	−178.8 (2)
C1—C6—C7—N2	−157.0 (3)	C10—C11—C15—C16	−0.4 (4)
C7—N2—C8—O1	1.4 (3)	C14—C15—C16—C17	−178.1 (3)
C7—N2—C8—C9	−176.7 (3)	C11—C15—C16—C17	0.8 (4)
N1—O1—C8—N2	−1.1 (3)	C15—C16—C17—C18	−0.3 (4)
N1—O1—C8—C9	177.3 (2)	O2—C10—C18—C17	179.4 (2)
C10—O2—C9—C8	175.3 (2)	C11—C10—C18—C17	0.7 (4)
N2—C8—C9—O2	4.4 (4)	C16—C17—C18—C10	−0.4 (4)
O1—C8—C9—O2	−173.7 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1W···N2	0.79 (4)	2.20 (4)	2.988 (3)	171 (4)
O1W—H2W···N3	0.81 (4)	2.00 (4)	2.810 (3)	174 (4)
C9—H9A···O1Wⁱ	0.97	2.54	3.437 (3)	154
C12—H12A···O1Wⁱⁱ	0.93	2.51	3.268 (4)	139

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

Experimental details

Crystal data
Chemical formula	C₁₈H₁₃N₃O₂·H₂O
M_r	321.33
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	293
a, b, c (Å)	7.0430 (14), 7.5800 (15), 29.114 (6)
β (°)	95.33 (3)
V (Å³)	1547.6 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.30 × 0.20 × 0.10

Data collection
Diffractometer	Enraf–Nonius CAD-4
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.972, 0.990
No. of measured, independent and observed [I > 2σ(I)] reflections	3101, 2853, 1608
R_int	0.025
(sin θ/λ)_max (Å⁻¹)	0.603

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.052, 0.144, 0.95
No. of reflections	2853
No. of parameters	223
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.15, −0.15

Computer programs: CAD-4 EXPRESS (Enraf–Nonius, 1994), XCAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1W···N2	0.79 (4)	2.20 (4)	2.988 (3)	171 (4)
O1W—H2W···N3	0.81 (4)	2.00 (4)	2.810 (3)	174 (4)
C9—H9A···O1Wⁱ	0.97	2.54	3.437 (3)	154
C12—H12A···O1Wⁱⁱ	0.93	2.51	3.268 (4)	139

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

References

Enraf–Nonius (1994). CAD-4 EXPRESS. Enraf–Nonius, Delft, The Netherlands. Google Scholar
Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany. Google Scholar
Katritzky, A. R., Ji, F. B. & Fan, W. Q. (1992). Heterocycl. Chem. 29, 1519–1523. CrossRef CAS Google Scholar
Liu, Z.-Q., Wang, H.-B., Pu, Y.-Q. & Yan, X.-C. (2006). Acta Cryst. E62, o1131–o1132. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351–359. CrossRef IUCr Journals Web of Science Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Shishue, C. & Henry, J. S. (1989). J Heterocycl. Chem. 26, 125–128. Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar

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