Methyl N-(3-cyano­picolino­yl)-l-tryptophanate

Ovdiichuk, O.; Hordiyenko, O.; Voitenko, Z.; Arrault, A.; Medviediev, V.

doi:10.1107/S160053681303153X

organic compounds

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ISSN: 2056-9890

Volume 69| Part 12| December 2013| Page o1810

doi:10.1107/S160053681303153X

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Methyl N-(3-cyanopicolinoyl)-L-tryptophanate

Olga Ovdiichuk,^a Olga Hordiyenko,^a Zoia Voitenko,^a Axelle Arrault ^b and Volodymyr Medviediev ^c ^*

^aKyiv National Taras Shevchenko University, Department of Chemistry, Volodymyrska str. 64, 01601 Kyiv, Ukraine, ^bLaboratoire de Chimie Physique Macromoleculaire, UMR 7568, ENSIC, BP 451, 54001 Nancy, France, and ^cSTC "Institute for Single Crystals", National Academy of Science of Ukraine, Lenina ave. 60, 61001, Khar'kov, Ukraine
^*Correspondence e-mail: vmedvedev@xray.isc.kharkov.com

(Received 13 November 2013; accepted 19 November 2013; online 23 November 2013)

In the title compound, C₁₉H₁₆N₄O₃, the stereocenter has an L configuration; L-tryptophan methyl ester hydrochloride being used as a starting material. The indole ring system and the pyridine ring are inclined to one another by 13.55 (14)°. In the crystal, adjacent molecules are linked via N—H⋯O hydrogen bonds, forming chains propagating along the c-axis direction.

CCDC reference: 972687

Related literature

Cyano-substituted compounds, like the title compound, are useful as intermediates in the synthesis of N-hydroxybenzamidines, see: Peterlin-Mašič & Kikelj (2001 ). For the synthesis of the title compound, see: Devillers et al. (2002 ). For the biological activity of 1,2,4-oxadiazole derivatives, see: Kundu et al. (2012 ); Sakamoto et al. (2007 ); Tyrkov & Sukhenko (2004 ).

Experimental

Crystal data

C₁₉H₁₆N₄O₃
M_r = 348.36
Monoclinic, P 2₁
a = 7.473 (2) Å
b = 11.977 (4) Å
c = 9.661 (3) Å
β = 91.01 (2)°
V = 864.6 (4) Å³
Z = 2
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 293 K
0.34 × 0.29 × 0.21 mm

Data collection

Agilent Xcalibur Sapphire3 diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ) T_min = 0.753, T_max = 1.000
9857 measured reflections
4832 independent reflections
2596 reflections with I > 2σ(I)
R_int = 0.047

Refinement

R[F² > 2σ(F²)] = 0.051
wR(F²) = 0.133
S = 0.93
4832 reflections
236 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.14 e Å⁻³
Absolute structure: Flack parameter determined using 855 quotients [(I⁺)−(I⁻)]/[(I⁺)+(I⁻)] (Parsons et al., 2013 )
Absolute structure parameter: −0.001 (3)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N4—H4⋯O1ⁱ	0.86	2.29	2.987 (3)	138
Symmetry code: (i) x, y, z-1.

Data collection: CrysAlis PRO (Agilent, 2011); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS2013 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008); molecular graphics: OLEX2 (Dolomanov et al., 2009 ); software used to prepare material for publication: OLEX2.

Supporting information

CCDC reference: 972687

Crystal structure: contains datablock I. DOI: 10.1107/S160053681303153X/su2666sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681303153X/su2666Isup2.hkl

Supporting information file. DOI: 10.1107/S160053681303153X/su2666Isup3.cdx

Supporting information file. DOI: 10.1107/S160053681303153X/su2666Isup4.cml

checkCIF report

Comment top

Cyano substituted compounds like the title compound are useful as intermediates in the synthesis of N-hydroxybenzamidines (Peterlin-Mašič & Kikelj, 2001). Substituted N-hydroxybenzamidines as well as their heterocyclic analogs are key intermediates in the synthesis of pharmaceutically important derivatives of 1,2,4-oxadiazole. The latter are well known for their anticancer (Kundu et al., 2012), anti-HIV (Sakamoto et al., 2007), and anti-microbial activities (Tyrkov & Sukhenko, 2004). In our studies on N-hydroxyamidines, of a heterocyclic nature from corresponding cyano derivatives, we synthesized the title compound and report herein on its crystal structure.

The molecular structure of the title compound is illustrated in Fig. 1. The stereo center, C8, has an L-configuration similar to the starting material L-tryptophan methyl ester hydrochloride. The dihedral angle between the indole ring system (N4/C12-C19; maximum deviation 0.033 (3) Å for atom C15) and pyridine ring (N1/C1-C4/C6) is 13.55 (14)°.

In the crystal, adjacent molecules are linked via N—H···O hydrogen bonds, forming chains propagating along the c axis direction (Table 1).

Related literature top

Cyano-substituted compounds, like the title compound, are useful as intermediates in the synthesis of N-hydroxybenzamidines, see: Peterlin-Mašič & Kikelj (2001). For the synthesis of the title compound, see: Devillers et al. (2002). For the biological activity of 1,2,4-oxadiazole derivatives, see: Kundu et al. (2012); Sakamoto et al. (2007); Tyrkov & Sukhenko (2004).

Experimental top

The title compound was synthesized according to the literature procedure (Devillers et al., 2002). 2-Cyanonicotinic acid (5 mmol) was dissolved in CH₂Cl₂ (30 ml), then triethylamine (10 mmol), L-tryptophan methyl ester hydrochloride (5 mmol) and N-hydroxybenzotriazole (5 mmol) were added to the solution. The mixture was stirred at 273 K and EDCI (5.05 mmol; 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide hydroiodide) was added. Then, the mixture was stirred at room temperature over night. The residue was diluted in CH₂Cl₂, washed with a solution of 0.1M HCl (3 × 15 ml), brine (20 ml) and then dried over MgSO₄ and concentrated under vacuo. The solid obtained was purified by column chromatography (CH₂Cl₂:MeOH 94:6). The title compound is a byproduct and crystallized as pale-yellow block-like crystals, suitable for X-ray diffraction analysis, by slow evaporation of a solution in dichloromethane and methanol (9:1).

Computing details top

Data collection: CrysAlis PRO (Agilent, 2011); cell refinement: CrysAlis PRO (Agilent, 2011); data reduction: CrysAlis PRO (Agilent, 2011); program(s) used to solve structure: SHELXS2013 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

Figures top

Fig. 1. The molecular structure of the title compound, with atom labelling. Displacement ellipsoids are drawn at the 30% probability level.

Methyl N-(3-cyanopicolinoyl)-L-tryptophanate top

Crystal data top

C₁₉H₁₆N₄O₃	F(000) = 364
M_r = 348.36	D_x = 1.338 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.7107 Å
Hall symbol: P 2yb	Cell parameters from 1601 reflections
a = 7.473 (2) Å	θ = 3.2–32.1°
b = 11.977 (4) Å	µ = 0.09 mm⁻¹
c = 9.661 (3) Å	T = 293 K
β = 91.01 (2)°	Block, colourless
V = 864.6 (4) Å³	0.34 × 0.29 × 0.21 mm
Z = 2

Data collection top

Agilent Xcalibur Sapphire3 diffractometer	4832 independent reflections
Radiation source: Enhance (Mo) X-ray Source	2596 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.047
Detector resolution: 16.1827 pixels mm^-1	θ_max = 30.0°, θ_min = 3.2°
ω scans	h = −10→10
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	k = −16→16
T_min = 0.753, T_max = 1.000	l = −13→13
9857 measured reflections

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)] = 0.051	H-atom parameters constrained
wR(F²) = 0.133	w = 1/[σ²(F_o²) + (0.0481P)²] where P = (F_o² + 2F_c²)/3
S = 0.93	(Δ/σ)_max = 0.002
4832 reflections	Δρ_max = 0.20 e Å⁻³
236 parameters	Δρ_min = −0.14 e Å⁻³
1 restraint	Absolute structure: Flack parameter determined using 855 quotients [(I⁺)-(I^-)]/[(I⁺)+(I^-)] (Parsons et al., 2013)
64 constraints	Absolute structure parameter: −0.001 (3)
Primary atom site location: structure-invariant direct methods

Crystal data top

C₁₉H₁₆N₄O₃	V = 864.6 (4) Å³
M_r = 348.36	Z = 2
Monoclinic, P2₁	Mo Kα radiation
a = 7.473 (2) Å	µ = 0.09 mm⁻¹
b = 11.977 (4) Å	T = 293 K
c = 9.661 (3) Å	0.34 × 0.29 × 0.21 mm
β = 91.01 (2)°

Data collection top

Agilent Xcalibur Sapphire3 diffractometer	4832 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	2596 reflections with I > 2σ(I)
T_min = 0.753, T_max = 1.000	R_int = 0.047
9857 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.051	H-atom parameters constrained
wR(F²) = 0.133	Δρ_max = 0.20 e Å⁻³
S = 0.93	Δρ_min = −0.14 e Å⁻³
4832 reflections	Absolute structure: Flack parameter determined using 855 quotients [(I⁺)-(I^-)]/[(I⁺)+(I^-)] (Parsons et al., 2013)
236 parameters	Absolute structure parameter: −0.001 (3)
1 restraint

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.

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

	x	y	z	U_iso*/U_eq
O1	0.3366 (4)	0.9180 (2)	0.4295 (2)	0.0820 (8)
O2	−0.0128 (4)	1.0476 (3)	0.1272 (4)	0.0933 (9)
O3	0.1275 (3)	1.2086 (2)	0.1722 (3)	0.0744 (8)
N1	0.2235 (4)	0.7036 (2)	0.1931 (3)	0.0593 (7)
N2	0.4469 (6)	0.7467 (3)	0.6623 (4)	0.0918 (12)
N3	0.2808 (4)	0.9245 (2)	0.2012 (3)	0.0588 (7)
H3	0.2553	0.8865	0.1280	0.071*
N4	0.3014 (4)	0.9839 (3)	−0.2741 (3)	0.0649 (8)
H4	0.2870	0.9343	−0.3376	0.078*
C1	0.2040 (5)	0.5917 (3)	0.1847 (4)	0.0733 (11)
H1	0.1587	0.5615	0.1026	0.088*
C2	0.2477 (5)	0.5201 (3)	0.2913 (5)	0.0779 (12)
H2	0.2344	0.4434	0.2802	0.094*
C3	0.3103 (5)	0.5626 (4)	0.4126 (4)	0.0710 (10)
H3A	0.3404	0.5156	0.4860	0.085*
C4	0.3291 (4)	0.6783 (3)	0.4258 (3)	0.0565 (9)
C5	0.3958 (5)	0.7217 (3)	0.5548 (4)	0.0692 (10)
C6	0.2835 (4)	0.7458 (3)	0.3133 (3)	0.0540 (8)
C7	0.3022 (5)	0.8708 (3)	0.3205 (3)	0.0544 (8)
C8	0.2987 (4)	1.0447 (3)	0.1894 (3)	0.0534 (8)
H8	0.3446	1.0731	0.2783	0.064*
C9	0.1191 (5)	1.0983 (3)	0.1613 (3)	0.0576 (9)
C10	−0.0323 (6)	1.2707 (4)	0.1397 (6)	0.0924 (15)
H10A	−0.0786	1.2479	0.0508	0.139*
H10B	−0.0049	1.3490	0.1377	0.139*
H10C	−0.1201	1.2567	0.2089	0.139*
C11	0.4336 (5)	1.0773 (3)	0.0766 (3)	0.0611 (9)
H11A	0.4658	1.1551	0.0895	0.073*
H11B	0.5414	1.0333	0.0906	0.073*
C12	0.3694 (4)	1.0617 (3)	−0.0696 (3)	0.0555 (8)
C13	0.3676 (5)	0.9647 (3)	−0.1435 (3)	0.0628 (9)
H13	0.4058	0.8957	−0.1100	0.075*
C14	0.2617 (5)	1.0954 (3)	−0.2872 (3)	0.0558 (9)
C15	0.3002 (4)	1.1473 (3)	−0.1602 (3)	0.0521 (8)
C16	0.2762 (5)	1.2624 (3)	−0.1484 (4)	0.0651 (10)
H16	0.3016	1.2987	−0.0653	0.078*
C17	0.2146 (6)	1.3211 (3)	−0.2616 (5)	0.0776 (12)
H17	0.1990	1.3979	−0.2546	0.093*
C18	0.1748 (5)	1.2681 (4)	−0.3863 (5)	0.0800 (12)
H18	0.1324	1.3099	−0.4610	0.096*
C19	0.1972 (5)	1.1552 (4)	−0.4010 (3)	0.0680 (10)
H19	0.1701	1.1197	−0.4843	0.082*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.138 (2)	0.0690 (16)	0.0390 (13)	0.0108 (16)	−0.0117 (14)	−0.0018 (12)
O2	0.0744 (18)	0.0795 (19)	0.125 (3)	−0.0159 (16)	−0.0208 (17)	0.0269 (18)
O3	0.0749 (18)	0.0649 (16)	0.0831 (18)	0.0101 (13)	−0.0101 (13)	−0.0138 (13)
N1	0.0617 (18)	0.0628 (18)	0.0533 (18)	0.0036 (14)	−0.0028 (14)	−0.0073 (14)
N2	0.136 (3)	0.090 (2)	0.0489 (19)	0.045 (2)	−0.0133 (19)	0.0005 (18)
N3	0.0815 (19)	0.0571 (17)	0.0374 (15)	−0.0026 (15)	−0.0072 (13)	−0.0031 (12)
N4	0.088 (2)	0.0628 (18)	0.0445 (17)	−0.0164 (16)	0.0091 (14)	−0.0101 (14)
C1	0.074 (3)	0.071 (3)	0.074 (3)	−0.003 (2)	−0.008 (2)	−0.014 (2)
C2	0.075 (3)	0.060 (2)	0.099 (4)	−0.0003 (19)	−0.003 (2)	0.002 (2)
C3	0.072 (2)	0.067 (2)	0.074 (3)	0.010 (2)	−0.004 (2)	0.012 (2)
C4	0.0557 (19)	0.063 (2)	0.051 (2)	0.0115 (15)	0.0030 (15)	0.0044 (16)
C5	0.087 (3)	0.066 (2)	0.054 (2)	0.026 (2)	0.0042 (19)	0.0076 (19)
C6	0.0508 (19)	0.064 (2)	0.0478 (19)	0.0073 (16)	0.0032 (14)	−0.0031 (16)
C7	0.063 (2)	0.064 (2)	0.0362 (18)	0.0110 (16)	−0.0013 (15)	0.0013 (15)
C8	0.069 (2)	0.0526 (19)	0.0380 (16)	−0.0012 (16)	−0.0088 (14)	−0.0014 (15)
C9	0.061 (2)	0.065 (2)	0.0465 (18)	−0.0050 (17)	0.0004 (15)	0.0072 (16)
C10	0.079 (3)	0.084 (3)	0.114 (4)	0.028 (2)	−0.002 (2)	−0.002 (3)
C11	0.064 (2)	0.066 (2)	0.0531 (19)	−0.0022 (18)	−0.0010 (15)	0.0000 (17)
C12	0.0613 (19)	0.0580 (19)	0.0474 (17)	−0.0095 (17)	0.0079 (14)	−0.0039 (16)
C13	0.079 (2)	0.058 (2)	0.051 (2)	−0.0090 (18)	0.0086 (17)	−0.0012 (17)
C14	0.060 (2)	0.061 (2)	0.0473 (18)	−0.0087 (16)	0.0130 (15)	0.0006 (16)
C15	0.0559 (18)	0.0554 (19)	0.0454 (17)	−0.0082 (16)	0.0117 (14)	−0.0022 (16)
C16	0.073 (2)	0.061 (2)	0.062 (2)	−0.0071 (18)	0.0122 (18)	−0.0032 (19)
C17	0.080 (3)	0.067 (2)	0.087 (3)	0.003 (2)	0.021 (2)	0.005 (2)
C18	0.080 (3)	0.092 (3)	0.069 (3)	0.009 (2)	0.015 (2)	0.018 (2)
C19	0.071 (2)	0.088 (3)	0.0456 (19)	−0.007 (2)	0.0086 (16)	0.0029 (19)

Geometric parameters (Å, º) top

O1—C7	1.219 (4)	C8—H8	0.9800
O2—C9	1.199 (4)	C8—C9	1.507 (5)
O3—C9	1.327 (4)	C8—C11	1.547 (4)
O3—C10	1.437 (5)	C10—H10A	0.9600
N1—C1	1.351 (5)	C10—H10B	0.9600
N1—C6	1.337 (4)	C10—H10C	0.9600
N2—C5	1.141 (5)	C11—H11A	0.9700
N3—H3	0.8600	C11—H11B	0.9700
N3—C7	1.327 (4)	C11—C12	1.495 (5)
N3—C8	1.451 (4)	C12—C13	1.364 (5)
N4—H4	0.8600	C12—C15	1.438 (5)
N4—C13	1.366 (4)	C13—H13	0.9300
N4—C14	1.374 (5)	C14—C15	1.401 (4)
C1—H1	0.9300	C14—C19	1.391 (5)
C1—C2	1.375 (6)	C15—C16	1.394 (5)
C2—H2	0.9300	C16—H16	0.9300
C2—C3	1.354 (6)	C16—C17	1.372 (6)
C3—H3A	0.9300	C17—H17	0.9300
C3—C4	1.399 (6)	C17—C18	1.389 (6)
C4—C5	1.431 (5)	C18—H18	0.9300
C4—C6	1.392 (5)	C18—C19	1.370 (6)
C6—C7	1.505 (5)	C19—H19	0.9300

C9—O3—C10	117.4 (3)	O3—C10—H10A	109.5
C6—N1—C1	117.5 (3)	O3—C10—H10B	109.5
C7—N3—H3	118.7	O3—C10—H10C	109.5
C7—N3—C8	122.7 (3)	H10A—C10—H10B	109.5
C8—N3—H3	118.7	H10A—C10—H10C	109.5
C13—N4—H4	125.6	H10B—C10—H10C	109.5
C13—N4—C14	108.9 (3)	C8—C11—H11A	108.4
C14—N4—H4	125.6	C8—C11—H11B	108.4
N1—C1—H1	118.3	H11A—C11—H11B	107.4
N1—C1—C2	123.4 (4)	C12—C11—C8	115.6 (3)
C2—C1—H1	118.3	C12—C11—H11A	108.4
C1—C2—H2	120.4	C12—C11—H11B	108.4
C3—C2—C1	119.2 (4)	C13—C12—C11	126.9 (3)
C3—C2—H2	120.4	C13—C12—C15	106.8 (3)
C2—C3—H3A	120.5	C15—C12—C11	126.3 (3)
C2—C3—C4	119.0 (4)	N4—C13—H13	125.1
C4—C3—H3A	120.5	C12—C13—N4	109.9 (3)
C3—C4—C5	118.1 (3)	C12—C13—H13	125.1
C6—C4—C3	118.7 (3)	N4—C14—C15	108.0 (3)
C6—C4—C5	123.1 (3)	N4—C14—C19	130.1 (3)
N2—C5—C4	173.8 (4)	C19—C14—C15	121.8 (3)
N1—C6—C4	122.2 (3)	C14—C15—C12	106.4 (3)
N1—C6—C7	116.5 (3)	C16—C15—C12	134.5 (3)
C4—C6—C7	121.3 (3)	C16—C15—C14	119.0 (3)
O1—C7—N3	123.1 (3)	C15—C16—H16	120.5
O1—C7—C6	121.3 (3)	C17—C16—C15	118.9 (4)
N3—C7—C6	115.6 (3)	C17—C16—H16	120.5
N3—C8—H8	107.9	C16—C17—H17	119.3
N3—C8—C9	110.7 (3)	C16—C17—C18	121.3 (4)
N3—C8—C11	111.6 (3)	C18—C17—H17	119.3
C9—C8—H8	107.9	C17—C18—H18	119.5
C9—C8—C11	110.8 (3)	C19—C18—C17	121.1 (4)
C11—C8—H8	107.9	C19—C18—H18	119.5
O2—C9—O3	124.3 (3)	C14—C19—H19	121.1
O2—C9—C8	124.0 (3)	C18—C19—C14	117.8 (4)
O3—C9—C8	111.6 (3)	C18—C19—H19	121.1

N1—C1—C2—C3	1.4 (6)	C8—C11—C12—C13	−81.6 (4)
N1—C6—C7—O1	171.7 (3)	C8—C11—C12—C15	99.6 (4)
N1—C6—C7—N3	−8.9 (4)	C9—C8—C11—C12	−50.2 (4)
N3—C8—C9—O2	−13.3 (5)	C10—O3—C9—O2	−0.6 (6)
N3—C8—C9—O3	169.9 (3)	C10—O3—C9—C8	176.3 (3)
N3—C8—C11—C12	73.6 (4)	C11—C8—C9—O2	111.1 (4)
N4—C14—C15—C12	1.3 (3)	C11—C8—C9—O3	−65.8 (4)
N4—C14—C15—C16	178.0 (3)	C11—C12—C13—N4	−179.2 (3)
N4—C14—C19—C18	−177.9 (3)	C11—C12—C15—C14	178.4 (3)
C1—N1—C6—C4	1.5 (5)	C11—C12—C15—C16	2.4 (6)
C1—N1—C6—C7	−179.4 (3)	C12—C15—C16—C17	176.0 (3)
C1—C2—C3—C4	−0.1 (6)	C13—N4—C14—C15	−1.4 (4)
C2—C3—C4—C5	−179.9 (3)	C13—N4—C14—C19	177.7 (3)
C2—C3—C4—C6	−0.3 (5)	C13—C12—C15—C14	−0.7 (3)
C3—C4—C6—N1	−0.4 (5)	C13—C12—C15—C16	−176.6 (4)
C3—C4—C6—C7	−179.4 (3)	C14—N4—C13—C12	1.0 (4)
C4—C6—C7—O1	−9.2 (5)	C14—C15—C16—C17	0.4 (5)
C4—C6—C7—N3	170.1 (3)	C15—C12—C13—N4	−0.2 (4)
C5—C4—C6—N1	179.2 (3)	C15—C14—C19—C18	1.2 (5)
C5—C4—C6—C7	0.1 (5)	C15—C16—C17—C18	0.4 (6)
C6—N1—C1—C2	−2.0 (6)	C16—C17—C18—C19	−0.5 (6)
C7—N3—C8—C9	−109.7 (4)	C17—C18—C19—C14	−0.3 (5)
C7—N3—C8—C11	126.5 (3)	C19—C14—C15—C12	−178.0 (3)
C8—N3—C7—O1	0.8 (6)	C19—C14—C15—C16	−1.2 (5)
C8—N3—C7—C6	−178.5 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4···O1ⁱ	0.86	2.29	2.987 (3)	138

Symmetry code: (i) x, y, z−1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4···O1ⁱ	0.86	2.29	2.987 (3)	137.6

Symmetry code: (i) x, y, z−1.

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Volume 69| Part 12| December 2013| Page o1810

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