1,3-Di-3-pyridyl-2,3-dihydro-1H-naphth[1,2-e][1,3]oxazine

Şen, B.; Turgut, Z.; Pelit, E.; Aygün, M.

doi:10.1107/S1600536808003887

organic compounds

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Volume 64| Part 3| March 2008| Page o573

doi:10.1107/S1600536808003887

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1,3-Di-3-pyridyl-2,3-dihydro-1H-naphth[1,2-e][1,3]oxazine

Betül Şen,^a ^* Zuhal Turgut,^b Emel Pelit ^b and Muhittin Aygün ^a

^aDepartment of Physics, Dokuz Eylül University, 35160 Buca-Izmir, Turkey, and ^bDepartment of Chemistry, Yιldιz Technical University, 34210 Davutpaşa Campus-Istanbul, Turkey
^*Correspondence e-mail: betul.sen@deu.edu.tr

(Received 18 January 2008; accepted 5 February 2008; online 13 February 2008)

In the crystal structure of the title compound, C₂₂H₁₇N₃O, the oxazine ring has a half-chair conformation. The dihedral angles between the best least-squares plane through the pyridine rings and the planar part (O–C–C–C–N) of the oxazine ring are 72.14 (6) and 35.44 (7)°, the smaller angle involving the pyridine ring adjacent to the oxazine O atom. The molecule has two stereogenic centers at the oxazine carbons, RS and SR. The crystal packing reveals that symmetry-related molecules are linked by intermolecular N—H⋯N hydrogen bonds to form chains parallel to the b axis.

Related literature

For related literature, see: Kurz et al. (2005 ); Turgut et al. (2007 ); Szatmari et al. (2003 , 2004 ); Bernstein et al. (1995 ); Cremer & Pople (1975 ).

Experimental

Crystal data

C₂₂H₁₇N₃O
M_r = 339.39
Monoclinic, P 2₁ /c
a = 12.1720 (8) Å
b = 8.0444 (6) Å
c = 18.7716 (15) Å
β = 112.615 (5)°
V = 1696.7 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 293 (2) K
0.28 × 0.22 × 0.12 mm

Data collection

Stoe IPDSII diffractometer
Absorption correction: none
15207 measured reflections
3703 independent reflections
1786 reflections with I > 2σ(I)
R_int = 0.124

Refinement

R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.092
S = 0.80
3703 reflections
304 parameters
All H-atom parameters refined
Δρ_max = 0.12 e Å⁻³
Δρ_min = −0.13 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯N3ⁱ	0.98 (2)	2.04 (2)	3.009 (2)	170.7 (17)
Symmetry code: (i) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: X-AREA (Stoe & Cie, 2002 ); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ) and PLATON (Spek, 2003 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808003887/su2043sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808003887/su2043Isup2.hkl

checkCIF report

Comment top

1,3-oxazine heterocycles are of interest because they constitute an important class of natural and non-natural products. Many of them exhibit biological activity such as analgesic, anticonvulsant, antitubercular, antibacterial and anticancer (Kurz et al., 2005; Turgut et al., 2007). In addition, they can be used as intermediates in the synthesis of N-substituted amino alcohols or in enantioselective synthesis of chiral amines. The tautomeric character of the 1,3-O,N-heterocycles offers a great number of synthetic possibilities (Szatmari et al., 2003; Szatmari et al., 2004).

Atoms (C11, C20, C21 and O1) of the oxazine six-membered ring are planar to within 0.014 Å. The oxazine ring adopts a half-chair conformation, with atom C22 and N1 deviating by -0.375 (3) Å and 0.308 (3) Å, respectively, from the mean plane formed by atoms (C11, C20, C21 and O1). The ring puckering parameters for the oxazine ring are Q = 0.451 (2) Å, θ = 126.2 (2)° and ϕ = 92.4 (3) ° (Cremer & Pople, 1975). The dihedral angles made by the best least-squares plane through all six atoms of the oxazine ring with the mean planes of the pyridine rings (N2/C1—C5) and (N3/C6—C10) are 79.62 (9)° and 36.40 (9)°, respectively. The sum of the angles at N1 of the oxazine ring is 334.1°, in accordance with sp³-hybridization. The H atoms bonded to atoms C22 and C21 of the oxazine ring are axial and trans to one another. The structure is centrosymmetric so the absolute configurations of the two stereogenic centres, C21 and C22, are RS and SR, respectively.

In the crystal structure, intermolecular N1—H1···N3ⁱ hydrogen bonds (Table 1) link the molecules to form an infinite one-dimensional polymeric chain. In this manner a C(6) chain (Bernstein et al., 1995) is formed and the axis of the polymeric chain runs co-linear with the crystallographic [010] direction of the monoclinic unit cell (Fig. 2).

Related literature top

For related literature, see: Kurz et al. (2005); Turgut et al. (2007); Szatmari et al. (2003, 2004); Bernstein et al. (1995); Cremer & Pople (1975).

Experimental top

The title compound was prepared by cyclization reactions realised using 2-naphthol and pyridine-3-carbaldehyde in the presence of dry methanolic ammonia (Fig. 3). The structure of the title compound has been clarified by FTIR, MS and NMR techniques and confirmed by elemental analysis.

Pyridin-3-carbaldehyde (2 mmol; freshly distilled if liquid) and 25% methanolic ammonia solution (0.5 mL) were added to a solution of 2-naphthol (1 mmol) in absolute MeOH (0.5 ml). The mixture was left to stand at ambient temperature for 2 days, during which time a crystalline product separated out. The crude product was filtered off, washed with cold MeOH (2x2mL), then purified by column chromatography with ethyl acetate/n-hexane (3:1). Pale-yellow crystals of the title compound, suitable for X-ray analysis, were obtained by slow evaporation of this solution.

¹H NMR (CDCl₃, δ (p.p.m.)): 5.34 (s, 1H, CH); 5.89 (s, 1H, CH); 7.21–7.89 (m, 10H, ArH); 8.50–8.89 (m, 4H, pyridine)

¹³C NMR (CDCl₃, δ (p.p.m.)): 56.23, 81.75, 124.37, 133.67, 139.76, 148.27, 150.52, 154.3

FTIR(KBr, cm^-1, ν) 3335, 3056,3034, 1622,1596,1260,1233,1023,928

Computing details top

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA (Stoe & Cie, 2002); data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPIII (Burnett & Johnson, 1996) and PLATON (Spek, 2003); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

	Fig. 1. An ORTEPIII (Burnett & Johnson, 1996) view of the title compound with the atomic numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are shown as spheres of arbitrary size.
	Fig. 2. The crystal packing diagram of the title compound showing the infinite zigzag chain along the b axis, formed through N—H···N hydrogen bonding (dashed lines) [Symmetry codes: (*) 1 - x,1/2 + y,1/2 - z].
	Fig. 3. The formation of the title compound.

1,3-Di-3-pyridyl-2,3-dihydro-1H-naphth[1,2-e][1,3]oxazine top

Crystal data top

C₂₂H₁₇N₃O	F(000) = 712
M_r = 339.39	D_x = 1.329 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 10289 reflections
a = 12.1720 (8) Å	θ = 1.7–27.2°
b = 8.0444 (6) Å	µ = 0.08 mm⁻¹
c = 18.7716 (15) Å	T = 293 K
β = 112.615 (5)°	Prism, pale yellow
V = 1696.7 (2) Å³	0.28 × 0.22 × 0.12 mm
Z = 4

Data collection top

Stoe IPDSII diffractometer	1786 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.124
Graphite monochromator	θ_max = 27.2°, θ_min = 2.4°
Detector resolution: 6.67 pixels mm^-1	h = −15→15
ω and ϕ scans	k = −10→10
15207 measured reflections	l = −24→24
3703 independent 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)] = 0.041	All H-atom parameters refined
wR(F²) = 0.092	w = 1/[σ²(F_o²) + (0.0317P)²] where P = (F_o² + 2F_c²)/3
S = 0.80	(Δ/σ)_max < 0.001
3703 reflections	Δρ_max = 0.12 e Å⁻³
304 parameters	Δρ_min = −0.13 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: 0.0155 (15)

Crystal data top

C₂₂H₁₇N₃O	V = 1696.7 (2) Å³
M_r = 339.39	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 12.1720 (8) Å	µ = 0.08 mm⁻¹
b = 8.0444 (6) Å	T = 293 K
c = 18.7716 (15) Å	0.28 × 0.22 × 0.12 mm
β = 112.615 (5)°

Data collection top

Stoe IPDSII diffractometer	1786 reflections with I > 2σ(I)
15207 measured reflections	R_int = 0.124
3703 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	0 restraints
wR(F²) = 0.092	All H-atom parameters refined
S = 0.80	Δρ_max = 0.12 e Å⁻³
3703 reflections	Δρ_min = −0.13 e Å⁻³
304 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	0.50525 (11)	0.70176 (16)	0.05782 (6)	0.0613 (3)
N1	0.34476 (13)	0.63357 (19)	0.09666 (7)	0.0530 (4)
N2	0.07931 (16)	0.2535 (2)	0.01583 (9)	0.0797 (5)
N3	0.61988 (16)	0.4333 (2)	0.30101 (8)	0.0708 (5)
C1	0.20165 (16)	0.4668 (2)	−0.00607 (8)	0.0515 (4)
C2	0.22195 (18)	0.3658 (2)	−0.05879 (10)	0.0624 (5)
C3	0.1718 (2)	0.2087 (3)	−0.07310 (11)	0.0721 (6)
C4	0.1012 (2)	0.1592 (3)	−0.03549 (11)	0.0750 (6)
C5	0.13038 (19)	0.4030 (3)	0.02947 (10)	0.0664 (5)
C6	0.55109 (16)	0.5779 (2)	0.17981 (8)	0.0518 (4)
C7	0.54203 (19)	0.4545 (2)	0.22813 (10)	0.0619 (5)
C8	0.7097 (2)	0.5402 (3)	0.32714 (11)	0.0717 (6)
C9	0.7258 (2)	0.6678 (3)	0.28396 (10)	0.0713 (6)
C10	0.64504 (18)	0.6866 (2)	0.20842 (9)	0.0621 (5)
C11	0.42404 (16)	0.7472 (2)	−0.01352 (8)	0.0521 (4)
C12	0.4760 (2)	0.8298 (2)	−0.05937 (10)	0.0581 (5)
C13	0.40609 (19)	0.8731 (2)	−0.13285 (10)	0.0614 (5)
C14	0.28339 (18)	0.8404 (2)	−0.16314 (9)	0.0571 (5)
C15	0.2110 (2)	0.8834 (3)	−0.24001 (10)	0.0703 (6)
C16	0.0929 (2)	0.8602 (3)	−0.26809 (12)	0.0854 (7)
C17	0.0389 (2)	0.7933 (3)	−0.22063 (12)	0.0884 (7)
C18	0.10616 (19)	0.7473 (3)	−0.14611 (10)	0.0703 (6)
C19	0.23078 (17)	0.7670 (2)	−0.11493 (9)	0.0548 (5)
C20	0.30495 (16)	0.7173 (2)	−0.03826 (8)	0.0506 (4)
C21	0.25461 (17)	0.6395 (2)	0.01656 (8)	0.0530 (4)
C22	0.45819 (16)	0.5869 (2)	0.09848 (8)	0.0526 (4)
H1	0.3522 (17)	0.738 (3)	0.1247 (10)	0.080 (6)*
H2	0.2726 (17)	0.408 (2)	−0.0873 (9)	0.073 (5)*
H3	0.1834 (19)	0.141 (3)	−0.1108 (12)	0.099 (7)*
H4	0.0621 (19)	0.051 (3)	−0.0461 (11)	0.089 (7)*
H5	0.1146 (18)	0.475 (3)	0.0680 (10)	0.083 (6)*
H7	0.4767 (18)	0.367 (3)	0.2099 (10)	0.077 (6)*
H8	0.7714 (19)	0.522 (3)	0.3822 (11)	0.094 (7)*
H9	0.7932 (19)	0.744 (3)	0.3052 (10)	0.083 (6)*
H10	0.6560 (18)	0.777 (3)	0.1759 (10)	0.090 (6)*
H12	0.5600 (18)	0.853 (2)	−0.0360 (9)	0.064 (5)*
H13	0.4472 (17)	0.928 (2)	−0.1648 (9)	0.076 (5)*
H15	0.2541 (18)	0.935 (3)	−0.2732 (10)	0.087 (6)*
H16	0.041 (2)	0.891 (3)	−0.3203 (13)	0.113 (8)*
H17	−0.047 (2)	0.776 (3)	−0.2404 (12)	0.107 (8)*
H18	0.0647 (16)	0.705 (2)	−0.1138 (9)	0.066 (5)*
H21	0.1904 (15)	0.710 (2)	0.0184 (8)	0.055 (5)*
H22	0.4510 (15)	0.472 (2)	0.0725 (8)	0.057 (5)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0548 (8)	0.0777 (9)	0.0510 (6)	−0.0024 (6)	0.0199 (6)	0.0111 (6)
N1	0.0553 (10)	0.0593 (10)	0.0451 (7)	−0.0015 (7)	0.0201 (7)	−0.0059 (6)
N2	0.0853 (14)	0.0791 (13)	0.0802 (10)	−0.0210 (10)	0.0380 (10)	−0.0002 (9)
N3	0.0791 (13)	0.0742 (12)	0.0544 (9)	−0.0034 (10)	0.0205 (8)	0.0110 (7)
C1	0.0464 (11)	0.0572 (11)	0.0479 (8)	−0.0006 (8)	0.0147 (8)	0.0004 (7)
C2	0.0677 (14)	0.0614 (12)	0.0625 (10)	−0.0053 (10)	0.0296 (10)	−0.0082 (9)
C3	0.0791 (16)	0.0637 (13)	0.0711 (12)	−0.0062 (11)	0.0261 (11)	−0.0124 (10)
C4	0.0768 (16)	0.0669 (14)	0.0712 (12)	−0.0135 (12)	0.0172 (11)	0.0009 (11)
C5	0.0717 (15)	0.0705 (13)	0.0615 (10)	−0.0078 (11)	0.0305 (10)	−0.0007 (10)
C6	0.0556 (12)	0.0525 (10)	0.0492 (9)	0.0008 (9)	0.0223 (8)	−0.0024 (7)
C7	0.0701 (15)	0.0624 (12)	0.0539 (10)	−0.0053 (10)	0.0246 (10)	0.0031 (9)
C8	0.0690 (16)	0.0815 (15)	0.0561 (11)	−0.0004 (12)	0.0146 (10)	0.0068 (10)
C9	0.0666 (15)	0.0794 (15)	0.0596 (11)	−0.0132 (12)	0.0152 (10)	0.0003 (10)
C10	0.0683 (14)	0.0639 (12)	0.0529 (10)	−0.0049 (10)	0.0217 (9)	0.0019 (9)
C11	0.0582 (13)	0.0539 (10)	0.0433 (8)	0.0026 (9)	0.0183 (8)	0.0005 (7)
C12	0.0592 (14)	0.0595 (11)	0.0568 (10)	−0.0026 (10)	0.0236 (9)	0.0017 (8)
C13	0.0733 (15)	0.0580 (11)	0.0573 (10)	−0.0009 (10)	0.0301 (10)	0.0073 (8)
C14	0.0625 (14)	0.0563 (11)	0.0516 (9)	0.0025 (9)	0.0209 (9)	0.0041 (8)
C15	0.0777 (18)	0.0720 (13)	0.0576 (11)	0.0021 (11)	0.0219 (11)	0.0106 (9)
C16	0.0798 (19)	0.1046 (18)	0.0596 (12)	−0.0013 (14)	0.0131 (12)	0.0173 (12)
C17	0.0630 (18)	0.119 (2)	0.0697 (13)	0.0006 (14)	0.0104 (11)	0.0228 (12)
C18	0.0620 (15)	0.0829 (14)	0.0636 (11)	−0.0025 (11)	0.0214 (10)	0.0088 (10)
C19	0.0585 (14)	0.0518 (10)	0.0526 (9)	0.0029 (9)	0.0196 (8)	0.0003 (8)
C20	0.0554 (13)	0.0495 (10)	0.0484 (8)	0.0016 (8)	0.0215 (8)	−0.0003 (7)
C21	0.0542 (12)	0.0591 (11)	0.0475 (9)	0.0053 (9)	0.0217 (8)	0.0007 (8)
C22	0.0566 (13)	0.0551 (11)	0.0480 (9)	0.0021 (9)	0.0222 (8)	0.0009 (8)

Geometric parameters (Å, º) top

O1—C11	1.3732 (19)	C9—C10	1.389 (3)
O1—C22	1.4492 (19)	C9—H9	0.98 (2)
N1—C22	1.419 (2)	C10—H10	0.99 (2)
N1—C21	1.483 (2)	C11—C20	1.363 (2)
N1—H1	0.97 (2)	C11—C12	1.415 (2)
N2—C4	1.331 (3)	C12—C13	1.359 (3)
N2—C5	1.332 (2)	C12—H12	0.962 (19)
N3—C8	1.328 (3)	C13—C14	1.404 (3)
N3—C7	1.342 (2)	C13—H13	1.017 (18)
C1—C2	1.374 (2)	C14—C15	1.414 (2)
C1—C5	1.381 (2)	C14—C19	1.422 (2)
C1—C21	1.522 (2)	C15—C16	1.341 (3)
C2—C3	1.384 (3)	C15—H15	1.040 (19)
C2—H2	1.017 (17)	C16—C17	1.402 (3)
C3—C4	1.365 (3)	C16—H16	0.97 (2)
C3—H3	0.95 (2)	C17—C18	1.372 (3)
C4—H4	0.98 (2)	C17—H17	0.98 (2)
C5—H5	1.002 (19)	C18—C19	1.409 (3)
C6—C10	1.374 (2)	C18—H18	0.988 (17)
C6—C7	1.378 (2)	C19—C20	1.431 (2)
C6—C22	1.512 (2)	C20—C21	1.520 (2)
C7—H7	1.02 (2)	C21—H21	0.975 (16)
C8—C9	1.368 (3)	C22—H22	1.032 (17)
C8—H8	1.03 (2)

C11—O1—C22	113.65 (13)	C13—C12—C11	119.1 (2)
C22—N1—C21	111.52 (12)	C13—C12—H12	123.7 (10)
C22—N1—H1	109.1 (11)	C11—C12—H12	117.2 (10)
C21—N1—H1	113.5 (11)	C12—C13—C14	121.13 (17)
C4—N2—C5	116.46 (18)	C12—C13—H13	116.8 (11)
C8—N3—C7	116.90 (17)	C14—C13—H13	122.0 (10)
C2—C1—C5	116.69 (17)	C13—C14—C15	121.03 (17)
C2—C1—C21	124.50 (16)	C13—C14—C19	119.30 (15)
C5—C1—C21	118.79 (15)	C15—C14—C19	119.65 (19)
C1—C2—C3	119.44 (18)	C16—C15—C14	121.3 (2)
C1—C2—H2	119.6 (10)	C16—C15—H15	122.1 (11)
C3—C2—H2	120.9 (10)	C14—C15—H15	116.6 (11)
C4—C3—C2	119.0 (2)	C15—C16—C17	119.8 (2)
C4—C3—H3	121.6 (14)	C15—C16—H16	123.2 (14)
C2—C3—H3	119.3 (13)	C17—C16—H16	116.9 (14)
N2—C4—C3	123.3 (2)	C18—C17—C16	120.6 (2)
N2—C4—H4	116.1 (12)	C18—C17—H17	118.8 (13)
C3—C4—H4	120.6 (12)	C16—C17—H17	120.5 (12)
N2—C5—C1	125.15 (18)	C17—C18—C19	121.2 (2)
N2—C5—H5	117.1 (11)	C17—C18—H18	118.3 (10)
C1—C5—H5	117.7 (11)	C19—C18—H18	120.5 (10)
C10—C6—C7	117.81 (16)	C18—C19—C14	117.29 (16)
C10—C6—C22	123.44 (15)	C18—C19—C20	123.26 (16)
C7—C6—C22	118.75 (17)	C14—C19—C20	119.45 (17)
N3—C7—C6	124.0 (2)	C11—C20—C19	118.07 (14)
N3—C7—H7	114.2 (10)	C11—C20—C21	119.66 (14)
C6—C7—H7	121.8 (10)	C19—C20—C21	122.23 (17)
N3—C8—C9	123.56 (19)	N1—C21—C20	111.47 (15)
N3—C8—H8	117.4 (12)	N1—C21—C1	108.81 (14)
C9—C8—H8	119.0 (12)	C20—C21—C1	115.12 (13)
C8—C9—C10	118.7 (2)	N1—C21—H21	105.9 (9)
C8—C9—H9	121.3 (11)	C20—C21—H21	108.8 (9)
C10—C9—H9	120.0 (11)	C1—C21—H21	106.2 (10)
C6—C10—C9	119.09 (18)	N1—C22—O1	113.38 (14)
C6—C10—H10	121.0 (11)	N1—C22—C6	112.33 (12)
C9—C10—H10	119.9 (12)	O1—C22—C6	105.59 (14)
C20—C11—O1	123.91 (14)	N1—C22—H22	108.7 (9)
C20—C11—C12	122.79 (15)	O1—C22—H22	107.5 (8)
O1—C11—C12	113.30 (17)	C6—C22—H22	109.2 (9)

C5—C1—C2—C3	−0.3 (3)	C13—C14—C19—C18	175.59 (17)
C21—C1—C2—C3	178.03 (18)	C15—C14—C19—C18	−2.6 (3)
C1—C2—C3—C4	1.4 (3)	C13—C14—C19—C20	−4.4 (2)
C5—N2—C4—C3	0.1 (3)	C15—C14—C19—C20	177.40 (16)
C2—C3—C4—N2	−1.3 (3)	O1—C11—C20—C19	−178.17 (14)
C4—N2—C5—C1	1.0 (3)	C12—C11—C20—C19	2.2 (2)
C2—C1—C5—N2	−0.9 (3)	O1—C11—C20—C21	4.2 (2)
C21—C1—C5—N2	−179.35 (18)	C12—C11—C20—C21	−175.39 (15)
C8—N3—C7—C6	0.7 (3)	C18—C19—C20—C11	−178.01 (17)
C10—C6—C7—N3	−0.6 (3)	C14—C19—C20—C11	1.9 (2)
C22—C6—C7—N3	179.19 (17)	C18—C19—C20—C21	−0.5 (3)
C7—N3—C8—C9	−0.1 (3)	C14—C19—C20—C21	179.47 (16)
N3—C8—C9—C10	−0.6 (3)	C22—N1—C21—C20	−41.2 (2)
C7—C6—C10—C9	−0.1 (3)	C22—N1—C21—C1	86.79 (17)
C22—C6—C10—C9	−179.90 (17)	C11—C20—C21—N1	10.0 (2)
C8—C9—C10—C6	0.7 (3)	C19—C20—C21—N1	−167.51 (15)
C22—O1—C11—C20	13.0 (2)	C11—C20—C21—C1	−114.56 (18)
C22—O1—C11—C12	−167.37 (14)	C19—C20—C21—C1	67.9 (2)
C20—C11—C12—C13	−3.9 (3)	C2—C1—C21—N1	−109.53 (19)
O1—C11—C12—C13	176.41 (15)	C5—C1—C21—N1	68.8 (2)
C11—C12—C13—C14	1.3 (3)	C2—C1—C21—C20	16.4 (3)
C12—C13—C14—C15	−179.09 (18)	C5—C1—C21—C20	−165.26 (17)
C12—C13—C14—C19	2.7 (3)	C21—N1—C22—O1	61.15 (19)
C13—C14—C15—C16	−176.6 (2)	C21—N1—C22—C6	−179.25 (14)
C19—C14—C15—C16	1.6 (3)	C11—O1—C22—N1	−46.19 (18)
C14—C15—C16—C17	0.5 (4)	C11—O1—C22—C6	−169.58 (13)
C15—C16—C17—C18	−1.6 (4)	C10—C6—C22—N1	−111.91 (19)
C16—C17—C18—C19	0.5 (4)	C7—C6—C22—N1	68.3 (2)
C17—C18—C19—C14	1.6 (3)	C10—C6—C22—O1	12.1 (2)
C17—C18—C19—C20	−178.5 (2)	C7—C6—C22—O1	−167.64 (15)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···N3ⁱ	0.98 (2)	2.04 (2)	3.009 (2)	170.7 (17)

Symmetry code: (i) −x+1, y+1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₂₂H₁₇N₃O
M_r	339.39
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	12.1720 (8), 8.0444 (6), 18.7716 (15)
β (°)	112.615 (5)
V (Å³)	1696.7 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.28 × 0.22 × 0.12

Data collection
Diffractometer	Stoe IPDSII diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	15207, 3703, 1786
R_int	0.124
(sin θ/λ)_max (Å⁻¹)	0.643

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.092, 0.80
No. of reflections	3703
No. of parameters	304
H-atom treatment	All H-atom parameters refined
Δρ_max, Δρ_min (e Å⁻³)	0.12, −0.13

Computer programs: X-AREA (Stoe & Cie, 2002), X-RED32 (Stoe & Cie, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEPIII (Burnett & Johnson, 1996) and PLATON (Spek, 2003), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···N3ⁱ	0.98 (2)	2.04 (2)	3.009 (2)	170.7 (17)

Symmetry code: (i) −x+1, y+1/2, −z+1/2.

Acknowledgements

The authors acknowledge the Faculty of Arts and Sciences, Ondokuz Mayıs University, Turkey, for the use of the Stoe IPDSII diffractometer (purchased under grant No. F.279 of the University Research Fund), and Dokuz Eylül University Research Funds (Project No. 04.KB.FEN.100).

References

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