4-{2-Meth­oxy-6-[(4-methyl­phen­yl)imino­meth­yl]phen­oxy}phthalonitrile

Yazıcı, S.; Akkaya, A.; Ağar, E.; Şenel, İ.; Büyükgüngör, O.

doi:10.1107/S1600536809015402

organic compounds

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ISSN: 2056-9890

Volume 65| Part 5| May 2009| Page o1172

doi:10.1107/S1600536809015402

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4-{2-Methoxy-6-[(4-methylphenyl)iminomethyl]phenoxy}phthalonitrile

Serap Yazıcı,^a Abdullah Akkaya,^a Erbil Ağar,^b İsmet Şenel ^a and Orhan Büyükgüngör ^a ^*

^aDepartment of Physics, Faculty of Arts and Sciences, Ondokuz Mayıs University, TR-55139 Kurupelit–Samsun, Turkey, and ^bDepartment of Chemistry, Faculty of Arts and Sciences, Ondokuz Mayıs University, TR-55139 Kurupelit–Samsun, Turkey
^*Correspondence e-mail: orhanb@omu.edu.tr

(Received 17 April 2009; accepted 24 April 2009; online 30 April 2009)

In the molecule of the title compound, C₂₃H₁₇N₃O₂, the methoxyphenyl ring is oriented at dihedral angles of 13.34 (12) and 88.83 (12)° with respect to the methylphenyl and phthalonitrile rings, respectively; the dihedral angle between methylphenyl and phthalonitrile rings is 89.67 (10)°. In the crystal structure, weak intermolecular C—H⋯N interactions link molecules into chains. A weak C—H⋯π interaction is also found..

Related literature

For a related structure, see: Ocak İskeleli et al. (2005 ). For general background to substituted phthalonitriles, see: McKeown (1998 ); Leznoff & Lever (1989–1996 ). For bond-length data, see: Allen et al. (1987 ).

Experimental

Crystal data

C₂₃H₁₇N₃O₂
M_r = 367.40
Monoclinic, P 2₁ /c
a = 9.3549 (5) Å
b = 23.6606 (13) Å
c = 8.9317 (5) Å
β = 97.256 (4)°
V = 1961.13 (19) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 296 K
0.67 × 0.36 × 0.20 mm

Data collection

Stoe IPDS-II diffractometer
Absorption correction: integration (X-RED32; Stoe & Cie, 2002 ) T_min = 0.703, T_max = 0.952
10306 measured reflections
3680 independent reflections
1962 reflections with I > 2σ(I)
R_int = 0.072

Refinement

R[F² > 2σ(F²)] = 0.048
wR(F²) = 0.122
S = 0.96
3680 reflections
253 parameters
H-atom parameters constrained
Δρ_max = 0.12 e Å⁻³
Δρ_min = −0.10 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4⋯N2ⁱ	0.93	2.62	3.483 (3)	154
C18—H18⋯Cg2ⁱⁱ	0.93	2.77	3.694 (3)	171
Symmetry codes: (i) $[-x+1, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (ii) x, y, z+1. Cg2 is the centroid of the C9–C14 ring.

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: ORTEP-3 for Windows (Farrugia, 1997 ) and PLATON (Spek, 2009 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809015402/hk2671sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809015402/hk2671Isup2.hkl

checkCIF report

Comment top

Substituted phthalonitriles are generally used for preparing symmetrically and unsymmetrically peripherally and non-peripherally substituted phthalocyanines and subphthalocyanines (McKeown, 1998; Leznoff & Lever, 1989-1996). In addition to their extensive use as dyes and pigments, phthalocyanines have found widespread applications in catalysis, in optical recording, as photoconductive materials, in photo-dynamic therapy and as chemical sensors (Leznoff & Lever, 1989-1996). We report herein the crystal structure of the title compound.

In the molecule of the title compound (Fig. 1), the bond lengths (Allen et al., 1987) and angles are within normal ranges. The N2≡C22 [1.133 (3) Å] and N3≡C23 [1.145 (3) Å] bonds show N≡C triple bond character and are in good agreement with the literature values (Ocak İskeleli et al., 2005). Rings A (C1-C6), B (C9-C14) and C (C16-C21) are, of course, planar, and they are oriented at dihedral angles of A/B = 13.34 (12), A/C = 88.83 (12) and B/C = 89.67 (10) °.

In the crystal structure, weak intermolecular C-H···N interactions (Table 1) link the molecules into chains (Fig. 2), in which they may be effective in the stabilization of the structure. There also exists a weak C-H···π interaction (Table 1).

Related literature top

For a related structure, see: Ocak İskeleli et al. (2005). For general background to substituted phthalonitriles, see: McKeown (1998); Leznoff & Lever (1989–1996). For bond-length data, see: Allen et al. (1987). Cg2 is the centroid of the C9–C14 ring.

Experimental top

For the preparation of the title compound, potasium carbonato (0.9 g, 6.58 mmol) was added to a solution of solid o-vaniline (0.5 g, 3.29 mmol) in DMF. The mixture was stirred for 30 min under nitrogen atmosphere. 4-Nitrophtalonitrile solution in DMF was added. The mixture was stirred for 48 h at 323 K under nitrogen atmosphere and poured into ice-water (150 g). The product 2-(3,4-dicyanophenoxy)-3-methoxybenzaldehyde was filtered off and washed with water. The title compound was prepared by refluxing a mixture of a solution containing 2-(3,4-Dicyanophenoxy)-3-methoxybenzaldehyde (0.5 g, 1.799 mmol) in ethanol (20 ml) and a solution containing 4-methylaniline (0.218 g 1.799 mmol) in ethanol (20 ml). The reaction mixture was stirred for 1 h under reflux. Crystals suitable for X-ray analysis were obtained from ethylalcohol by slow evaporation (yield; 55%, m.p. 427-429 K).

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: ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

	Fig. 1. The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. A partial packing diagram of the title compound. Hydrogen bonds are shown as dashed lines.

4-{2-Methoxy-6-[(4-methylphenyl)iminomethyl]phenoxy}phthalonitrile top

Crystal data top

C₂₃H₁₇N₃O₂	F(000) = 768
M_r = 367.40	D_x = 1.244 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9188 reflections
a = 9.3549 (5) Å	θ = 1.7–26.2°
b = 23.6606 (13) Å	µ = 0.08 mm⁻¹
c = 8.9317 (5) Å	T = 296 K
β = 97.256 (4)°	Prism, yellow
V = 1961.13 (19) Å³	0.67 × 0.36 × 0.20 mm
Z = 4

Data collection top

Stoe IPDS-II diffractometer	3680 independent reflections
Radiation source: fine-focus sealed tube	1962 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.072
Detector resolution: 6.67 pixels mm^-1	θ_max = 25.6°, θ_min = 1.7°
ω scans	h = −11→10
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	k = −28→28
T_min = 0.703, T_max = 0.952	l = −10→10
10306 measured reflections

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.122	H-atom parameters constrained
S = 0.96	w = 1/[σ²(F_o²) + (0.0491P)²] where P = (F_o² + 2F_c²)/3
3680 reflections	(Δ/σ)_max < 0.001
253 parameters	Δρ_max = 0.12 e Å⁻³
0 restraints	Δρ_min = −0.10 e Å⁻³

Crystal data top

C₂₃H₁₇N₃O₂	V = 1961.13 (19) Å³
M_r = 367.40	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 9.3549 (5) Å	µ = 0.08 mm⁻¹
b = 23.6606 (13) Å	T = 296 K
c = 8.9317 (5) Å	0.67 × 0.36 × 0.20 mm
β = 97.256 (4)°

Data collection top

Stoe IPDS-II diffractometer	3680 independent reflections
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	1962 reflections with I > 2σ(I)
T_min = 0.703, T_max = 0.952	R_int = 0.072
10306 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	0 restraints
wR(F²) = 0.122	H-atom parameters constrained
S = 0.96	Δρ_max = 0.12 e Å⁻³
3680 reflections	Δρ_min = −0.10 e Å⁻³
253 parameters

Special details top

Experimental. 140 frames, detector distance = 130 mm

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	0.38836 (16)	0.44741 (6)	0.57255 (15)	0.0725 (4)
O2	0.49525 (18)	0.52245 (6)	0.77461 (17)	0.0879 (5)
N1	0.0395 (2)	0.47793 (7)	0.26224 (19)	0.0737 (5)
N2	0.4483 (3)	0.21068 (11)	0.7035 (4)	0.1657 (14)
N3	0.1213 (3)	0.23410 (10)	0.9455 (3)	0.1180 (9)
C1	0.2188 (2)	0.51464 (8)	0.4521 (2)	0.0659 (6)
C2	0.1712 (3)	0.57046 (9)	0.4401 (2)	0.0768 (6)
H2	0.0969	0.5805	0.3657	0.092*
C3	0.2339 (3)	0.61054 (9)	0.5379 (2)	0.0798 (7)
H3	0.2028	0.6478	0.5273	0.096*
C4	0.3424 (3)	0.59675 (9)	0.6520 (2)	0.0760 (7)
H4	0.3828	0.6245	0.7181	0.091*
C5	0.3905 (2)	0.54177 (9)	0.6673 (2)	0.0687 (6)
C6	0.3289 (2)	0.50179 (8)	0.5654 (2)	0.0644 (5)
C7	0.5596 (3)	0.56217 (11)	0.8831 (3)	0.1040 (9)
H7A	0.6256	0.5429	0.9569	0.156*
H7B	0.4859	0.5800	0.9320	0.156*
H7C	0.6106	0.5903	0.8333	0.156*
C8	0.1525 (3)	0.46997 (9)	0.3529 (2)	0.0727 (6)
H8	0.1954	0.4344	0.3568	0.087*
C9	−0.0244 (2)	0.43225 (9)	0.1744 (2)	0.0683 (6)
C10	−0.0023 (3)	0.37542 (10)	0.2086 (2)	0.0818 (7)
H10	0.0624	0.3649	0.2917	0.098*
C11	−0.0759 (3)	0.33451 (10)	0.1202 (3)	0.0872 (7)
H11	−0.0599	0.2967	0.1450	0.105*
C12	−0.1731 (3)	0.34819 (11)	−0.0046 (3)	0.0870 (7)
C13	−0.1944 (3)	0.40459 (11)	−0.0376 (3)	0.0854 (7)
H13	−0.2589	0.4149	−0.1209	0.102*
C14	−0.1221 (2)	0.44613 (10)	0.0501 (2)	0.0761 (6)
H14	−0.1391	0.4839	0.0254	0.091*
C15	−0.2535 (4)	0.30258 (13)	−0.0997 (4)	0.1312 (12)
H15A	−0.2834	0.3170	−0.1993	0.197*
H15B	−0.3367	0.2913	−0.0543	0.197*
H15C	−0.1914	0.2706	−0.1059	0.197*
C16	0.3328 (2)	0.40673 (8)	0.6576 (2)	0.0626 (6)
C17	0.2221 (3)	0.41613 (8)	0.7412 (2)	0.0674 (6)
H17	0.1823	0.4520	0.7452	0.081*
C18	0.1699 (3)	0.37193 (9)	0.8193 (2)	0.0728 (6)
H18	0.0952	0.3784	0.8767	0.087*
C19	0.2270 (3)	0.31831 (9)	0.8135 (3)	0.0745 (6)
C20	0.3403 (3)	0.30971 (9)	0.7282 (3)	0.0793 (7)
C21	0.3937 (3)	0.35393 (9)	0.6509 (3)	0.0776 (7)
H21	0.4699	0.3481	0.5951	0.093*
C22	0.4004 (3)	0.25418 (11)	0.7156 (4)	0.1104 (10)
C23	0.1688 (3)	0.27176 (10)	0.8882 (3)	0.0904 (8)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0718 (10)	0.0594 (9)	0.0864 (10)	0.0058 (8)	0.0110 (8)	−0.0032 (7)
O2	0.0908 (12)	0.0751 (10)	0.0908 (10)	−0.0005 (9)	−0.0153 (9)	−0.0078 (8)
N1	0.0850 (14)	0.0644 (11)	0.0691 (10)	−0.0018 (10)	−0.0001 (10)	0.0018 (9)
N2	0.156 (3)	0.0656 (15)	0.262 (4)	0.0429 (17)	−0.026 (3)	−0.0140 (19)
N3	0.159 (3)	0.0703 (14)	0.1152 (17)	−0.0202 (15)	−0.0180 (16)	0.0176 (12)
C1	0.0758 (15)	0.0581 (12)	0.0637 (12)	−0.0014 (11)	0.0079 (11)	−0.0006 (9)
C2	0.0941 (18)	0.0625 (13)	0.0720 (13)	0.0039 (12)	0.0039 (12)	0.0086 (11)
C3	0.107 (2)	0.0508 (12)	0.0819 (15)	0.0015 (12)	0.0138 (14)	0.0061 (11)
C4	0.0931 (19)	0.0586 (13)	0.0759 (14)	−0.0114 (13)	0.0091 (13)	−0.0052 (10)
C5	0.0731 (15)	0.0603 (13)	0.0718 (13)	−0.0069 (11)	0.0056 (11)	−0.0004 (10)
C6	0.0700 (14)	0.0518 (11)	0.0722 (13)	0.0001 (11)	0.0119 (11)	0.0013 (10)
C7	0.101 (2)	0.1008 (19)	0.1020 (17)	−0.0055 (16)	−0.0182 (16)	−0.0239 (15)
C8	0.0841 (17)	0.0602 (13)	0.0723 (13)	0.0028 (12)	0.0044 (13)	−0.0034 (10)
C9	0.0737 (15)	0.0658 (13)	0.0644 (12)	−0.0017 (11)	0.0045 (11)	0.0013 (10)
C10	0.0931 (19)	0.0699 (15)	0.0781 (14)	−0.0045 (14)	−0.0053 (13)	0.0021 (11)
C11	0.098 (2)	0.0698 (15)	0.0914 (16)	−0.0100 (14)	0.0039 (14)	−0.0001 (13)
C12	0.0813 (18)	0.0915 (18)	0.0861 (16)	−0.0141 (14)	0.0018 (14)	−0.0090 (14)
C13	0.0804 (18)	0.0994 (19)	0.0735 (15)	−0.0033 (15)	−0.0012 (13)	0.0018 (13)
C14	0.0740 (16)	0.0793 (15)	0.0734 (13)	0.0026 (13)	0.0026 (12)	0.0045 (11)
C15	0.130 (3)	0.120 (2)	0.134 (2)	−0.032 (2)	−0.022 (2)	−0.0259 (19)
C16	0.0624 (14)	0.0501 (11)	0.0714 (13)	0.0010 (10)	−0.0061 (11)	−0.0064 (10)
C17	0.0770 (16)	0.0477 (11)	0.0750 (13)	0.0066 (11)	−0.0003 (12)	−0.0028 (9)
C18	0.0842 (18)	0.0575 (13)	0.0750 (13)	−0.0002 (12)	0.0029 (12)	0.0007 (10)
C19	0.0826 (17)	0.0507 (13)	0.0829 (14)	−0.0001 (12)	−0.0184 (13)	0.0014 (10)
C20	0.0807 (17)	0.0462 (12)	0.1017 (17)	0.0116 (12)	−0.0253 (15)	−0.0064 (11)
C21	0.0691 (16)	0.0583 (13)	0.1014 (16)	0.0125 (12)	−0.0047 (12)	−0.0136 (12)
C22	0.104 (2)	0.0576 (15)	0.159 (3)	0.0155 (15)	−0.0258 (19)	−0.0029 (15)
C23	0.113 (2)	0.0544 (14)	0.0954 (17)	−0.0048 (14)	−0.0198 (15)	0.0066 (12)

Geometric parameters (Å, º) top

C1—C6	1.384 (3)	C11—H11	0.9300
C1—C2	1.393 (3)	C12—C13	1.376 (3)
C1—C8	1.465 (3)	C12—C15	1.513 (3)
C2—C3	1.370 (3)	C13—C14	1.379 (3)
C2—H2	0.9300	C13—H13	0.9300
C3—C4	1.384 (3)	C14—H14	0.9300
C3—H3	0.9300	C15—H15A	0.9600
C4—C5	1.377 (3)	C15—H15B	0.9600
C4—H4	0.9300	C15—H15C	0.9600
C5—O2	1.361 (2)	C16—O1	1.369 (2)
C5—C6	1.386 (3)	C16—C17	1.369 (3)
C6—O1	1.400 (2)	C16—C21	1.378 (3)
C7—O2	1.427 (3)	C17—C18	1.381 (3)
C7—H7A	0.9600	C17—H17	0.9300
C7—H7B	0.9600	C18—C19	1.380 (3)
C7—H7C	0.9600	C18—H18	0.9300
C8—N1	1.262 (3)	C19—C20	1.397 (3)
C8—H8	0.9300	C19—C23	1.431 (4)
C9—C14	1.385 (3)	C20—C21	1.381 (3)
C9—C10	1.389 (3)	C20—C22	1.439 (3)
C9—N1	1.422 (3)	C21—H21	0.9300
C10—C11	1.378 (3)	C22—N2	1.133 (3)
C10—H10	0.9300	C23—N3	1.145 (3)
C11—C12	1.385 (3)

C16—O1—C6	119.67 (16)	C10—C11—H11	119.1
C5—O2—C7	117.49 (18)	C12—C11—H11	119.1
C8—N1—C9	120.00 (19)	C13—C12—C11	117.5 (2)
C6—C1—C2	117.71 (19)	C13—C12—C15	121.6 (2)
C6—C1—C8	120.19 (19)	C11—C12—C15	121.0 (3)
C2—C1—C8	122.1 (2)	C12—C13—C14	121.5 (2)
C3—C2—C1	120.1 (2)	C12—C13—H13	119.2
C3—C2—H2	120.0	C14—C13—H13	119.2
C1—C2—H2	120.0	C13—C14—C9	120.8 (2)
C2—C3—C4	121.4 (2)	C13—C14—H14	119.6
C2—C3—H3	119.3	C9—C14—H14	119.6
C4—C3—H3	119.3	C12—C15—H15A	109.5
C5—C4—C3	119.7 (2)	C12—C15—H15B	109.5
C5—C4—H4	120.2	H15A—C15—H15B	109.5
C3—C4—H4	120.2	C12—C15—H15C	109.5
O2—C5—C4	125.72 (19)	H15A—C15—H15C	109.5
O2—C5—C6	115.83 (19)	H15B—C15—H15C	109.5
C4—C5—C6	118.5 (2)	O1—C16—C17	123.69 (18)
C1—C6—C5	122.64 (19)	O1—C16—C21	115.2 (2)
C1—C6—O1	119.32 (17)	C17—C16—C21	121.1 (2)
C5—C6—O1	117.88 (19)	C16—C17—C18	119.5 (2)
O2—C7—H7A	109.5	C16—C17—H17	120.2
O2—C7—H7B	109.5	C18—C17—H17	120.2
H7A—C7—H7B	109.5	C19—C18—C17	121.0 (2)
O2—C7—H7C	109.5	C19—C18—H18	119.5
H7A—C7—H7C	109.5	C17—C18—H18	119.5
H7B—C7—H7C	109.5	C18—C19—C20	118.6 (2)
N1—C8—C1	122.4 (2)	C18—C19—C23	121.2 (3)
N1—C8—H8	118.8	C20—C19—C23	120.2 (2)
C1—C8—H8	118.8	C21—C20—C19	120.6 (2)
C14—C9—C10	118.1 (2)	C21—C20—C22	118.9 (3)
C14—C9—N1	116.8 (2)	C19—C20—C22	120.4 (3)
C10—C9—N1	125.02 (19)	C16—C21—C20	119.2 (2)
C11—C10—C9	120.3 (2)	C16—C21—H21	120.4
C11—C10—H10	119.9	C20—C21—H21	120.4
C9—C10—H10	119.9	N2—C22—C20	178.9 (4)
C10—C11—C12	121.8 (2)	N3—C23—C19	178.8 (3)

C1—C6—O1—C16	−91.4 (2)	C2—C1—C8—N1	−7.8 (3)
C5—C6—O1—C16	93.0 (2)	C14—C9—C10—C11	0.2 (4)
C17—C16—O1—C6	−1.5 (3)	N1—C9—C10—C11	176.3 (2)
C21—C16—O1—C6	176.75 (18)	C9—C10—C11—C12	0.1 (4)
C4—C5—O2—C7	1.3 (3)	C10—C11—C12—C13	−0.2 (4)
C6—C5—O2—C7	−179.0 (2)	C10—C11—C12—C15	−179.6 (3)
C1—C8—N1—C9	−176.67 (18)	C11—C12—C13—C14	−0.1 (4)
C14—C9—N1—C8	−162.8 (2)	C15—C12—C13—C14	179.4 (3)
C10—C9—N1—C8	21.0 (4)	C12—C13—C14—C9	0.4 (4)
C6—C1—C2—C3	0.5 (3)	C10—C9—C14—C13	−0.5 (3)
C8—C1—C2—C3	178.3 (2)	N1—C9—C14—C13	−176.9 (2)
C1—C2—C3—C4	−1.5 (4)	O1—C16—C17—C18	177.77 (19)
C2—C3—C4—C5	0.9 (4)	C21—C16—C17—C18	−0.4 (3)
C3—C4—C5—O2	−179.5 (2)	C16—C17—C18—C19	−0.5 (3)
C3—C4—C5—C6	0.8 (3)	C17—C18—C19—C20	0.8 (3)
C2—C1—C6—C5	1.2 (3)	C17—C18—C19—C23	−176.9 (2)
C8—C1—C6—C5	−176.7 (2)	C18—C19—C20—C21	−0.2 (3)
C2—C1—C6—O1	−174.27 (19)	C23—C19—C20—C21	177.5 (2)
C8—C1—C6—O1	7.9 (3)	C18—C19—C20—C22	−178.3 (2)
O2—C5—C6—C1	178.4 (2)	C23—C19—C20—C22	−0.6 (3)
C4—C5—C6—C1	−1.8 (3)	O1—C16—C21—C20	−177.32 (19)
O2—C5—C6—O1	−6.1 (3)	C17—C16—C21—C20	1.0 (3)
C4—C5—C6—O1	173.70 (19)	C19—C20—C21—C16	−0.7 (3)
C6—C1—C8—N1	169.9 (2)	C22—C20—C21—C16	177.4 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···N2ⁱ	0.93	2.62	3.483 (3)	154
C18—H18···Cg2ⁱⁱ	0.93	2.77	3.694 (3)	171

Symmetry codes: (i) −x+1, y+1/2, −z+3/2; (ii) x, y, z+1.

Experimental details

Crystal data
Chemical formula	C₂₃H₁₇N₃O₂
M_r	367.40
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	9.3549 (5), 23.6606 (13), 8.9317 (5)
β (°)	97.256 (4)
V (Å³)	1961.13 (19)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.67 × 0.36 × 0.20

Data collection
Diffractometer	Stoe IPDS-II diffractometer
Absorption correction	Integration (X-RED32; Stoe & Cie, 2002)
T_min, T_max	0.703, 0.952
No. of measured, independent and observed [I > 2σ(I)] reflections	10306, 3680, 1962
R_int	0.072
(sin θ/λ)_max (Å⁻¹)	0.609

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.122, 0.96
No. of reflections	3680
No. of parameters	253
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.12, −0.10

Computer programs: X-AREA (Stoe & Cie, 2002), X-RED32 (Stoe & Cie, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···N2ⁱ	0.93	2.62	3.483 (3)	154
C18—H18···Cg2ⁱⁱ	0.93	2.77	3.694 (3)	171

Symmetry codes: (i) −x+1, y+1/2, −z+3/2; (ii) x, y, z+1.

Acknowledgements

The authors wish to acknowledge the Faculty of Arts and Sciences, Ondokuz Mayıs University, Turkey, for the use of the Stoe IPDS-II diffractometer (purchased under grant No. F279 of the University Research Fund).

References

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