3-(2-Chloro­pyridin-3-yl)quinazoline-2,4(1H,3H)-dione chloro­form monosolvate

Riad, N.M.; Zlotos, D.P.; Holzgrabe, U.

doi:10.1107/S2414314617005806

organic compounds

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ISSN: 2414-3146

Volume 2| Part 4| April 2017| x170580

https://doi.org/10.1107/S2414314617005806

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3-(2-Chloropyridin-3-yl)quinazoline-2,4(1H,3H)-dione chloroform monosolvate

Noura M. Riad,^a Darius P. Zlotos ^a ^* and Ulrike Holzgrabe ^b

^aThe German University in Cairo, Department of Pharmaceutical Chemistry, New Cairo City, 11835 Cairo, Egypt, and ^bInstitute of Pharmacy and Food Chemistry, Wuerzburg University, 97074 Wuerzburg, Germany
^*Correspondence e-mail: darius.zlotos@guc.edu.eg

Edited by H. Stoeckli-Evans, University of Neuchâtel, Switzerland (Received 9 April 2017; accepted 18 April 2017; online 28 April 2017)

The solvated title compound, C₁₃H₈ClN₃O₂·CHCl₃, is a product of a condensation reaction between 2-amino-N-(2-chloropyridin-3-yl)benzamide and phosgene. The presence of the chlorine substituent in the pyridine ring forces the latter to adopt a nearly perpendicular orientation relative to the planar quinazoline ring (r.m.s. deviation = 0.04 Å), the two ring systems being inclined to one another by 84.28 (9)°. In the crystal, molecules are linked by pairs of N—H⋯O hydrogen bonds, forming inversion dimers with an R₂²(8) ring motif. The dimers are linked by C—H⋯O hydrogen bonds, forming ribbons propagating along the a-axis direction. The chloroform solvent molecules are linked to the organic molecule by C—H⋯N hydrogen bonds.

Keywords: crystal structure; quinazoline-2,4-dione; hydrogen bonding.

CCDC reference: 1024197

Structure description

The title compound results from our ongoing research aimed at the development of subtype-selective ligands for muscarinic receptors (Tahtaoui et al., 2004 ; Mohr et al., 2010 ). It was isolated as a side-product in the course of the synthesis of AFDX-type allosteric modulators of muscarinic M2 receptors (Mohr et al., 2004 ). Specifically, the incomplete condensation between ethyl 2-aminobenzoate and 3-amino-2-chloropyridine (Holzgrabe & Heller, 2003 ) gave the ring-opened 2-amino-N-(2-chloropyridin-3-yl)benzamide (1) in 23% yield. This compound, (1), was subjected to condensation with phosgene giving the title compound (2) in 85% yield. This two-step approach is of general interest for the synthesis of differently substituted (1H,3H)-quinazoline-2,4-diones.

The molecular structure of the title compound (2), which crystallized as a chloroform monosolvate, is shown in Fig. 1. The pyridine ring (N1/C1–C5) is nearly perpendicular to the planar quinazoline ring (N2/N3/C6–C13; r.m.s. deviation = 0.04 Å), making a dihedral angle of 84.28 (9)°.

Figure 1
The molecular structure of the solvated title compound, (2)·CHCl₃, with the atom labelling and displacement ellipsoids drawn at the 50% probability level.

In the crystal, molecules are linked by pairs of N—H⋯O hydrogen bonds forming inversion dimers, with an R₂²(8) ring motif (Fig. 2 and Table 1). The chloroform solvate molecules are linked to the organic molecule by C—H⋯N hydrogen bonds, and the dimers are linked by C—H⋯O hydrogen bonds, forming ribbons propagating along the a-axis direction (Fig. 2 and Table 1).

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3⋯O1ⁱ	0.88	1.91	2.791 (3)	175
C14—H14⋯N1ⁱⁱ	1.00	2.39	3.200 (3)	137
C3—H3A⋯O2ⁱⁱⁱ	0.95	2.48	3.123 (3)	125
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) x, y-1, z; (iii) x+1, y, z.

Figure 2
A view along the c axis of the crystal packing of the solvated title compound, (2)·CHCl₃. The hydrogen bonds are shown as dashed lines (see Table 1

). For clarity, only the H atoms involved in hydrogen bonding have been included.

Synthesis and crystallization

2-Amino-N-(2-chloropyridin-3-yl)benzamide (1).

3-Amino-2-chloropyridine (2.57 g, 20.0 mmol), ethyl 2-aminobenzoate (3.39 g, 20.5 mmol) and KO^tBu (7.29 g, 65.0 mmol) were suspended in dry 1,4-dioxane (100 ml) under argon. The mixture was heated by microwaves (gradient of heating: 2 min to 333 K; holding time: 10 min at 333 K; gradient of heating: 3 min from 333–373 K; holding time: 2.5 h at 373 K). After cooling to 298 K, the solution was treated with 1 M NaH₂PO₄ (60 ml) and stirred for 30 min. The dioxane was evaporated in vacuo and the residue was treated with 50 ml water. The solid obtained was filtered and dried. The product (1) was then purified by silica chromatography (ethyl acetate/petroleum ether 1:1, R_f = 0.78), giving a pale-yellow solid (yield: 1.16 g, 23.3%; m.p. 477.3 K). ¹H NMR (400 MHz, DMSO-d₆) δ 9.89 (1H, br, N—H), 8.29 (1H, dd, J = 4.7, 1.8 Hz), 8.07 (1H, dd, J = 7.9, 1.8 Hz), 7.74 (1H, dd, J = 8.1, 1.5 Hz), 7.49 (1H, dd, J = 7.9, 4.7 Hz), 7.24 (1H, ddd, J = 8.4, 7.1, 1.5 Hz), 6.79 (1H, dd, J = 8.4, 1.2 Hz), 6.62 (1H, ddd, J = 8.1, 7.1, 1.2 Hz), 6.47 (2H, br, NH₂). ¹³C NMR (100 MHz, DMSO-d₆) δ 168.27 (C= O), 150.73, 146.71 (C—Cl), 146.68 (CH), 136.96 (C), 133.22 (C), 132.82 (C), 129.25 (C), 123.85 (CH), 117.22 (C), 115.35 (C), 113.86 (C). IR (ATR, cm⁻¹): 3433 (NH), 3330, 3286 (NH₂), 3073 (CH), 1644 (C=O amide), 1616, 1578, 1569, 1503, 1486, 1391, 802, 743, 735. MS (ESI): m/z (%): 248.2 (M+1).

3-(2-Chloropyridin-3-yl)quinazoline-2,4-(1H,3H)dione (2).

Compound (1) (4.22 g, 20.0 mmol) and Hueunig's base (7.0 ml, 40.0 mmol) were dissolved in dry 1,4-dioxane (150 ml) under argon. A solution of 20% phosgene in toluene (18.5 ml, 35.0 mmol) was added dropwise over 30 min. The solution was heated using microwaves (gradient of heating: 3 min to 358 K; holding time: 2 h at 358 K). After cooling to 298 K, the mixture was quenched with 1.0 M NaH₂PO₄ (100 ml) and stirred for 1 h at room temperature. The dioxane was evaporated and the solid obtained was filtered by suction and dried over P₄O₁₀, giving a white solid (yield: 4.68 g, 85.5%; m.p. 510.6 K). The product was recrystallized from chloroform giving colourless block-like crystals of the title compound (2). ¹H NMR (400 MHz, CDCl₃) δ 10.52 (1H, br, N—H), 8.56 (1H, dd, J = 4.8, 1.8 Hz), 8.15 (1H, dd, J = 7.9, 1.1 Hz), 7.76 (1H, dd, J = 7.8, 1.8 Hz), 7.61 (1H, ddd, J = 8.1, 7.0, 1.1 Hz), 7.46 (1H, dd, J = 7.8, 4.8 Hz), 7.27 (1H, ddd, J = 7.9, 7.0, 1.0 Hz), 7.02 (1H, dd, J = 8.1, 1.0 Hz). ¹³C NMR (100 MHz, CDCl₃) δ 161.58 (C=O), 150.95 (C=O), 150.40 (C—Cl), 149.94 (CH), 139.64 (C), 138.87 (C), 135.94 (C), 129.94 (C), 128.73 (C), 123.99 (C), 123.39 (CH), 115.70 (C), 114.34 (C). IR (ATR, cm⁻¹): 3348 (NH), 3072 (CH), 1680 (C=O), 1730 (C=O), 1580, 734. MS (ESI): m/z (%): 274.6 (M+1).

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2.

Table 2
Experimental details

Crystal data
Chemical formula	C₁₃H₈ClN₃O₂·CHCl₃
M_r	393.04
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	5.6382 (11), 13.622 (3), 20.662 (4)
β (°)	92.289 (6)
V (Å³)	1585.7 (5)
Z	4
Radiation type	Mo Kα
μ (mm⁻¹)	0.76
Crystal size (mm)	0.59 × 0.32 × 0.26

Data collection
Diffractometer	Bruker APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2013 )
T_min, T_max	0.656, 0.980
No. of measured, independent and observed [I > 2σ(I)] reflections	15463, 3370, 2796
R_int	0.054
(sin θ/λ)_max (Å⁻¹)	0.634

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.109, 1.08
No. of reflections	3370
No. of parameters	208
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.45, −0.49
Computer programs: APEX2 and SAINT (Bruker, 2013), olex2.solve (Bourhis et al., 2015 ), SHELXL2014 (Sheldrick, 2015 ), Mercury (Macrae et al., 2008 ), OLEX2 (Dolomanov et al., 2009 ), SHELXL2014 (Sheldrick, 2015), enCIFer (Allen et al., 2004 ) and publCIF (Westrip (2010 ).

Structural data

CCDC reference: 1024197

Crystal structure: contains datablocks I, Global. DOI: https://doi.org/10.1107/S2414314617005806/su4148sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314617005806/su4148Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2414314617005806/su4148Isup3.cml

checkCIF report

Computing details top

Data collection: APEX2 (Bruker, 2013); cell refinement: SAINT (Bruker, 2013); data reduction: SAINT (Bruker, 2013); program(s) used to solve structure: olex2.solve (Bourhis et al., 2015); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009), SHELXL2014 (Sheldrick, 2015), enCIFer (Allen et al., 2004) and publCIF (Westrip (2010).

3-(2-Chloropyridin-3-yl)quinazoline-2,4(1H,3H)-dione chloroform monosolvate top

Crystal data top

C₁₃H₈ClN₃O₂·CHCl₃	F(000) = 792
M_r = 393.04	D_x = 1.646 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 5.6382 (11) Å	Cell parameters from 3659 reflections
b = 13.622 (3) Å	θ = 2.5–26.4°
c = 20.662 (4) Å	µ = 0.76 mm⁻¹
β = 92.289 (6)°	T = 100 K
V = 1585.7 (5) Å³	Block, colourless
Z = 4	0.59 × 0.32 × 0.26 mm

Data collection top

Bruker APEXII CCD diffractometer	2796 reflections with I > 2σ(I)
φ and ω scans	R_int = 0.054
Absorption correction: multi-scan (SADABS; Bruker, 2013)	θ_max = 26.8°, θ_min = 1.8°
T_min = 0.656, T_max = 0.980	h = −7→7
15463 measured reflections	k = −17→16
3370 independent reflections	l = −26→26

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.109	H-atom parameters constrained
S = 1.08	w = 1/[σ²(F_o²) + (0.0529P)² + 0.6894P] where P = (F_o² + 2F_c²)/3
3370 reflections	(Δ/σ)_max = 0.001
208 parameters	Δρ_max = 0.45 e Å⁻³
0 restraints	Δρ_min = −0.49 e Å⁻³

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Cl1	0.12965 (11)	0.78921 (4)	0.58061 (3)	0.02149 (16)
Cl2	0.36470 (11)	0.13451 (5)	0.50999 (3)	0.02813 (17)
Cl3	0.40964 (14)	0.12297 (5)	0.64924 (3)	0.03261 (19)
Cl4	−0.03576 (12)	0.07201 (5)	0.58295 (4)	0.03620 (19)
O2	0.1523 (3)	0.60895 (12)	0.73418 (7)	0.0176 (4)
O1	0.5724 (3)	0.60283 (12)	0.55085 (8)	0.0213 (4)
N2	0.3498 (3)	0.60913 (13)	0.64027 (9)	0.0136 (4)
N1	0.4692 (4)	0.87525 (14)	0.64811 (9)	0.0186 (4)
N3	0.2842 (4)	0.48850 (14)	0.56200 (9)	0.0172 (4)
H3	0.3204	0.4603	0.5254	0.021*
C10	−0.2711 (4)	0.36988 (17)	0.66329 (12)	0.0217 (5)
H10	−0.3989	0.3427	0.6859	0.026*
C11	−0.1409 (4)	0.44692 (16)	0.69008 (11)	0.0172 (5)
H11	−0.1781	0.4724	0.7313	0.021*
C5	0.6601 (4)	0.87655 (17)	0.68915 (11)	0.0191 (5)
H5	0.7306	0.9381	0.6997	0.023*
C6	0.4117 (4)	0.56808 (16)	0.58157 (10)	0.0158 (5)
C4	0.7592 (4)	0.79289 (17)	0.71677 (11)	0.0186 (5)
H4	0.8932	0.7968	0.7460	0.022*
C12	0.0464 (4)	0.48717 (16)	0.65602 (10)	0.0139 (4)
C9	−0.2150 (4)	0.33221 (17)	0.60333 (12)	0.0226 (5)
H9	−0.3059	0.2795	0.5853	0.027*
C3	0.6576 (4)	0.70314 (16)	0.70056 (11)	0.0168 (5)
H3A	0.7219	0.6441	0.7184	0.020*
C8	−0.0304 (5)	0.36989 (17)	0.56961 (12)	0.0209 (5)
H8	0.0080	0.3428	0.5290	0.025*
C7	0.1001 (4)	0.44849 (16)	0.59596 (11)	0.0156 (5)
C13	0.1806 (4)	0.57113 (16)	0.68188 (10)	0.0137 (4)
C2	0.4630 (4)	0.70030 (16)	0.65844 (10)	0.0135 (4)
C1	0.3755 (4)	0.78838 (16)	0.63368 (10)	0.0154 (5)
C14	0.2739 (4)	0.07115 (17)	0.57913 (11)	0.0181 (5)
H14	0.3274	0.0014	0.5759	0.022*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0248 (3)	0.0162 (3)	0.0229 (3)	0.0005 (2)	−0.0065 (2)	0.0010 (2)
Cl2	0.0266 (3)	0.0344 (4)	0.0234 (3)	−0.0062 (3)	0.0005 (2)	0.0095 (2)
Cl3	0.0510 (5)	0.0250 (3)	0.0219 (3)	−0.0152 (3)	0.0019 (3)	−0.0036 (2)
Cl4	0.0211 (3)	0.0288 (4)	0.0594 (5)	−0.0018 (3)	0.0103 (3)	0.0094 (3)
O2	0.0216 (9)	0.0148 (8)	0.0166 (8)	−0.0002 (7)	0.0025 (6)	−0.0021 (6)
O1	0.0281 (10)	0.0146 (8)	0.0218 (9)	−0.0078 (7)	0.0100 (7)	−0.0063 (6)
N2	0.0179 (10)	0.0071 (9)	0.0159 (9)	−0.0027 (7)	0.0020 (7)	−0.0021 (7)
N1	0.0277 (11)	0.0089 (9)	0.0191 (10)	−0.0023 (8)	0.0004 (8)	0.0001 (7)
N3	0.0237 (11)	0.0113 (9)	0.0168 (9)	−0.0052 (8)	0.0040 (8)	−0.0045 (7)
C10	0.0199 (13)	0.0121 (12)	0.0331 (14)	−0.0036 (10)	0.0026 (10)	0.0036 (9)
C11	0.0175 (12)	0.0120 (11)	0.0222 (12)	0.0021 (9)	0.0019 (9)	0.0026 (9)
C5	0.0266 (13)	0.0110 (11)	0.0197 (12)	−0.0048 (10)	0.0023 (9)	−0.0029 (8)
C6	0.0203 (12)	0.0096 (11)	0.0175 (11)	−0.0009 (9)	0.0018 (9)	−0.0006 (8)
C4	0.0192 (12)	0.0172 (12)	0.0194 (12)	−0.0025 (10)	−0.0010 (9)	−0.0026 (9)
C12	0.0153 (11)	0.0074 (10)	0.0189 (11)	0.0017 (9)	−0.0008 (8)	0.0022 (8)
C9	0.0228 (13)	0.0104 (11)	0.0344 (14)	−0.0053 (10)	−0.0006 (10)	−0.0018 (10)
C3	0.0206 (12)	0.0111 (11)	0.0190 (11)	0.0020 (9)	0.0035 (9)	−0.0009 (8)
C8	0.0274 (13)	0.0115 (11)	0.0239 (12)	−0.0021 (10)	0.0010 (10)	−0.0032 (9)
C7	0.0183 (12)	0.0081 (10)	0.0203 (11)	0.0006 (9)	0.0003 (9)	0.0014 (8)
C13	0.0150 (11)	0.0098 (10)	0.0165 (11)	0.0043 (9)	0.0009 (8)	0.0021 (8)
C2	0.0172 (11)	0.0089 (10)	0.0148 (10)	−0.0018 (9)	0.0053 (8)	−0.0020 (8)
C1	0.0197 (12)	0.0113 (11)	0.0152 (11)	−0.0011 (9)	0.0009 (8)	−0.0004 (8)
C14	0.0210 (12)	0.0113 (11)	0.0221 (12)	−0.0012 (10)	0.0024 (9)	−0.0004 (9)

Geometric parameters (Å, º) top

Cl1—C1	1.733 (2)	C11—H11	0.9500
Cl2—C14	1.763 (2)	C11—C12	1.404 (3)
Cl3—C14	1.759 (2)	C5—H5	0.9500
Cl4—C14	1.751 (2)	C5—C4	1.383 (3)
O2—C13	1.214 (3)	C4—H4	0.9500
O1—C6	1.222 (3)	C4—C3	1.385 (3)
N2—C6	1.393 (3)	C12—C7	1.392 (3)
N2—C13	1.408 (3)	C12—C13	1.461 (3)
N2—C2	1.439 (3)	C9—H9	0.9500
N1—C5	1.343 (3)	C9—C8	1.375 (4)
N1—C1	1.325 (3)	C3—H3A	0.9500
N3—H3	0.8800	C3—C2	1.373 (3)
N3—C6	1.354 (3)	C8—H8	0.9500
N3—C7	1.387 (3)	C8—C7	1.397 (3)
C10—H10	0.9500	C2—C1	1.387 (3)
C10—C11	1.383 (3)	C14—H14	1.0000
C10—C9	1.389 (3)

C6—N2—C13	125.71 (19)	C8—C9—C10	121.2 (2)
C6—N2—C2	116.71 (18)	C8—C9—H9	119.4
C13—N2—C2	117.53 (18)	C4—C3—H3A	120.3
C1—N1—C5	117.1 (2)	C2—C3—C4	119.3 (2)
C6—N3—H3	117.9	C2—C3—H3A	120.3
C6—N3—C7	124.24 (19)	C9—C8—H8	120.5
C7—N3—H3	117.9	C9—C8—C7	119.1 (2)
C11—C10—H10	120.0	C7—C8—H8	120.5
C11—C10—C9	120.1 (2)	N3—C7—C12	119.7 (2)
C9—C10—H10	120.0	N3—C7—C8	119.8 (2)
C10—C11—H11	120.2	C12—C7—C8	120.5 (2)
C10—C11—C12	119.6 (2)	O2—C13—N2	120.3 (2)
C12—C11—H11	120.2	O2—C13—C12	125.0 (2)
N1—C5—H5	118.3	N2—C13—C12	114.72 (18)
N1—C5—C4	123.4 (2)	C3—C2—N2	121.6 (2)
C4—C5—H5	118.3	C3—C2—C1	118.2 (2)
O1—C6—N2	120.9 (2)	C1—C2—N2	120.2 (2)
O1—C6—N3	123.4 (2)	N1—C1—Cl1	115.99 (17)
N3—C6—N2	115.66 (19)	N1—C1—C2	123.8 (2)
C5—C4—H4	120.9	C2—C1—Cl1	120.18 (17)
C5—C4—C3	118.1 (2)	Cl2—C14—H14	108.3
C3—C4—H4	120.9	Cl3—C14—Cl2	109.87 (12)
C11—C12—C13	120.8 (2)	Cl3—C14—H14	108.3
C7—C12—C11	119.6 (2)	Cl4—C14—Cl2	110.84 (13)
C7—C12—C13	119.6 (2)	Cl4—C14—Cl3	111.24 (13)
C10—C9—H9	119.4	Cl4—C14—H14	108.3

N2—C2—C1—Cl1	−0.1 (3)	C4—C3—C2—C1	0.0 (3)
N2—C2—C1—N1	179.9 (2)	C9—C10—C11—C12	0.6 (4)
N1—C5—C4—C3	0.8 (4)	C9—C8—C7—N3	−178.8 (2)
C10—C11—C12—C7	−0.5 (3)	C9—C8—C7—C12	1.0 (4)
C10—C11—C12—C13	177.5 (2)	C3—C2—C1—Cl1	−179.73 (17)
C10—C9—C8—C7	−1.0 (4)	C3—C2—C1—N1	0.2 (3)
C11—C10—C9—C8	0.2 (4)	C7—N3—C6—O1	−179.5 (2)
C11—C12—C7—N3	179.6 (2)	C7—N3—C6—N2	0.9 (3)
C11—C12—C7—C8	−0.3 (3)	C7—C12—C13—O2	−178.2 (2)
C11—C12—C13—O2	3.9 (3)	C7—C12—C13—N2	3.1 (3)
C11—C12—C13—N2	−174.84 (19)	C13—N2—C6—O1	−175.0 (2)
C5—N1—C1—Cl1	−179.98 (17)	C13—N2—C6—N3	4.6 (3)
C5—N1—C1—C2	0.1 (3)	C13—N2—C2—C3	84.3 (3)
C5—C4—C3—C2	−0.5 (3)	C13—N2—C2—C1	−95.3 (2)
C6—N2—C13—O2	174.7 (2)	C13—C12—C7—N3	1.6 (3)
C6—N2—C13—C12	−6.5 (3)	C13—C12—C7—C8	−178.3 (2)
C6—N2—C2—C3	−98.0 (3)	C2—N2—C6—O1	7.4 (3)
C6—N2—C2—C1	82.4 (3)	C2—N2—C6—N3	−172.91 (19)
C6—N3—C7—C12	−3.9 (3)	C2—N2—C13—O2	−7.8 (3)
C6—N3—C7—C8	176.0 (2)	C2—N2—C13—C12	171.01 (19)
C4—C3—C2—N2	−179.6 (2)	C1—N1—C5—C4	−0.6 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···O1ⁱ	0.88	1.91	2.791 (3)	175
C14—H14···N1ⁱⁱ	1.00	2.39	3.200 (3)	137
C3—H3A···O2ⁱⁱⁱ	0.95	2.48	3.123 (3)	125

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

Acknowledgements

The authors thank Andreas Lorbach and Todd B. Marder (Institute of Inorganic Chemistry, Wuerzburg University) for the data collection and structure solution. We appreciate the financial support provided to NSR by the Deutscher Akademischer Austauschdienst (DAAD).

Funding information

Funding for this research was provided by: Deutscher Akademischer Austauschdienst DAAD.

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