4-(4-Meth­oxy­pheneth­yl)-3,5-diphenyl-4H-1,2,4-triazole

Anuradha, G.; Vasuki, G.; Ünlüer, D.; Birinci, E.

doi:10.1107/S1600536812000359

organic compounds

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ISSN: 2056-9890

Volume 68| Part 2| February 2012| Page o392

doi:10.1107/S1600536812000359

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4-(4-Methoxyphenethyl)-3,5-diphenyl-4H-1,2,4-triazole

G. Anuradha,^a G. Vasuki,^b ^* Dilek Ünlüer ^c and Emrah Birinci ^c

^aDepartment of Physics, Saveetha School of Engineering, Saveetha University, Chennai-5, India, ^bDepartment of Physics, Kunthavai Naachiar Government Arts College (w) (Autonomous), Thanjavur-7, India, and ^cDepartment of Chemistry, Faculty of Arts and Sciences, Karadeniz Teknik University, Trabzon 61080, Turkey
^*Correspondence e-mail: vasuki.arasi@yahoo.com

(Received 29 December 2011; accepted 4 January 2012; online 14 January 2012)

In the title compound, C₂₃H₂₁N₃O, the dihedral angles formed by the mean plane of the triazole ring [maximum deviation = 0.007 (1) Å] and the three phenyl rings are 51.13 (8), 52.84 (8) and 47.04 (8)°. In the crystal, molecules are linked by weak C—H⋯N interactions, forming infinite chains propagating along the b-axis direction.

Related literature

For details of the synthesis, see: Ünver et al. (2011 ). For related structures and bond lengths and angles in triazole rings, see: Fun et al. (1999 ); Gurumoorthy et al. (2011 , 2010a ,b ); Bruno et al. (2003 ); Mazur et al. (2008 ); Sancak et al. (2005 ).

Experimental

Crystal data

C₂₃H₂₁N₃O
M_r = 355.43
Monoclinic, P 2₁ /n
a = 13.144 (5) Å
b = 7.411 (5) Å
c = 21.333 (5) Å
β = 106.835 (5)°
V = 1989.0 (16) Å³
Z = 4
Mo Kα radiation
μ = 0.07 mm⁻¹
T = 293 K
0.30 × 0.20 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 1999 ) T_min = 0.966, T_max = 0.991
17443 measured reflections
3492 independent reflections
2536 reflections with I > 2σ(I)
R_int = 0.037

Refinement

R[F² > 2σ(F²)] = 0.039
wR(F²) = 0.126
S = 1.03
3492 reflections
245 parameters
H-atom parameters constrained
Δρ_max = 0.15 e Å⁻³
Δρ_min = −0.12 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C16—H16A⋯N2ⁱ	0.97	2.62	3.542 (3)	160
Symmetry code: (i) x, y+1, z.

Data collection: APEX2 (Bruker, 2004 ); cell refinement: APEX2 and SAINT (Bruker, 2004); data reduction: SAINT and XPREP (Bruker, 2004); program(s) used to solve structure: SIR92 (Altomare et al., 1994 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: PLATON (Spek, 2009 ) and Mercury (Macrae et al., 2008 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812000359/su2362sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812000359/su2362Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812000359/su2362Isup3.cml

checkCIF report

Comment top

The present study is a continuation of our investigations on the structural characterization of 4H-1,2,4-triazole derivatives (Gurumoorthy et al., 2011, 2010a,b). We report herein the crystal structure of the title compound, which was studied to examine the structural activity relationships of a triazole with phenyl substituents.

In the title molecule (Fig. 1) the bond lengths and angles are in agreement with those found for closely related structures, for example, 1-(Benzoylmethyl)-4-(3,5-dimethyl-4H-1,2,4-triazol-4-yl)-3- (2-thienylmethyl)-1H-1,2,4-triazol-5(4H)-one [Sancak et al., 2005], 2-[4-Phenyl-5-(2-pyridyl)-4H- 1,2,4-triazol-3-yl]nicotinic acid: a case of solvent-dependent polymorphism [Mazur et al., 2008], and 4-[4-(Dimethylamino)benzylideneamino]-3,5-bis(2-pyridyl)-4H-1,2,4-triazole (Bruno et al., 2003)

The title molecule contains four planar rings, namely, a triazole ring A = (N1,N2,C8,N3,C7)] and three benzene rings, B = (C1-C6), C = (C9-C14) and D = (C17-C22). None of the aromatic rings are coplanar with the triazole ring, as observed in the related structure 4-(p-Methoxyphenyl)-3,5-bis(2-pyridyl)-4H-1,2,4-triazole [Fun et al., 1999]. In the title compound the three phenyl rings (B, C & D) are inclined to the triazole ring (A) by 51.13 (8), 52.84 (8) and 47.04 (8)°, respectively.

The bond angles C6—C7—N3 = 126.29 (14)° and C7—N3—C15 = 127.83 (12)° deviate significantly from the normal value of 120°, and angle N1—C7—C6 = 123.88 (14)° deviates from the normal value of 120°. Torsion angle C9—C8—N3—C15 = 13.1 (2) ° indicates that rings C and D have a Z-configuration across the C8—N3 bond. The C7—N3—C15—C16 torsion angle of 85.73 (18)° indicates that the triazole ring and the methoxy phenyl ring is substituted equatorially across the bond N3—C15. Torsion angles N2—N1—C7—C6 = 179.89 (14)° and N2—N1—C8—C9 = 179.40 (14)° indicate that the phenyl rings are substituted anti-periplanar to the triazole ring at atoms C7 and C8, respectively.

In the crystal, molecules are linked by a weak C—H···N interaction to form an infinite chain running along the b axis direction (Fig. 2).

Related literature top

For details of the synthesis, see: Ünver et al. (2011). For related structures and bond lengths and angles in triazole rings, see: Fun et al. (1999); Gurumoorthy et al. (2011, 2010a,b); Bruno et al. (2003; Mazur et al. (2008); Sancak et al. (2005).

Experimental top

The compound was synthesized following the published procedure (Ünver et al., 2011)

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2 and SAINT (Bruker, 2004); data reduction: SAINT and XPREP (Bruker, 2004); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title molecule, showing the numbering scheme and displacement ellipsoids drawn at the 50% probability level.
	Fig. 2. A view along the a axis of the crystal packing of the title compound, showing the C—H···N interactions as dashed cyan lines [see Table 1 for details].

4-(4-Methoxyphenethyl)-3,5-diphenyl-4H-1,2,4-triazole top

Crystal data top

C₂₃H₂₁N₃O	F(000) = 752
M_r = 355.43	D_x = 1.187 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3242 reflections
a = 13.144 (5) Å	θ = 2.5–25.1°
b = 7.411 (5) Å	µ = 0.07 mm⁻¹
c = 21.333 (5) Å	T = 293 K
β = 106.835 (5)°	Block, colourless
V = 1989.0 (16) Å³	0.30 × 0.20 × 0.20 mm
Z = 4

Data collection top

Bruker Kappa APEXII CCD diffractometer	3492 independent reflections
Radiation source: fine-focus sealed tube	2536 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.037
ω and ϕ scan	θ_max = 25.0°, θ_min = 2.9°
Absorption correction: multi-scan (SADABS; Bruker, 1999)	h = −15→15
T_min = 0.966, T_max = 0.991	k = −8→8
17443 measured reflections	l = −25→25

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)] = 0.039	H-atom parameters constrained
wR(F²) = 0.126	w = 1/[σ²(F_o²) + (0.0695P)² + 0.175P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max < 0.001
3492 reflections	Δρ_max = 0.15 e Å⁻³
245 parameters	Δρ_min = −0.12 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: 0.0094 (17)

Crystal data top

C₂₃H₂₁N₃O	V = 1989.0 (16) Å³
M_r = 355.43	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 13.144 (5) Å	µ = 0.07 mm⁻¹
b = 7.411 (5) Å	T = 293 K
c = 21.333 (5) Å	0.30 × 0.20 × 0.20 mm
β = 106.835 (5)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	3492 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 1999)	2536 reflections with I > 2σ(I)
T_min = 0.966, T_max = 0.991	R_int = 0.037
17443 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	0 restraints
wR(F²) = 0.126	H-atom parameters constrained
S = 1.03	Δρ_max = 0.15 e Å⁻³
3492 reflections	Δρ_min = −0.12 e Å⁻³
245 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
N3	0.12673 (9)	0.32890 (16)	0.22455 (6)	0.0434 (3)
N1	0.09718 (11)	0.05004 (17)	0.24966 (7)	0.0533 (4)
N2	0.10253 (11)	0.05178 (17)	0.18565 (7)	0.0529 (4)
C8	0.11935 (12)	0.2195 (2)	0.17167 (7)	0.0449 (4)
C7	0.11099 (12)	0.2166 (2)	0.27187 (7)	0.0456 (4)
O1	−0.23477 (10)	0.58453 (18)	0.37271 (6)	0.0733 (4)
C15	0.12614 (13)	0.52730 (19)	0.22388 (8)	0.0479 (4)
H15A	0.1705	0.5698	0.1977	0.058*
H15B	0.1564	0.5714	0.2682	0.058*
C16	0.01528 (13)	0.6037 (2)	0.19644 (8)	0.0520 (4)
H16A	0.0211	0.7294	0.1853	0.062*
H16B	−0.0198	0.5402	0.1562	0.062*
C9	0.13099 (13)	0.2774 (2)	0.10790 (7)	0.0474 (4)
C17	−0.05381 (13)	0.5917 (2)	0.24178 (8)	0.0472 (4)
C20	−0.17867 (13)	0.5789 (2)	0.32786 (8)	0.0530 (4)
C18	−0.02777 (13)	0.6922 (2)	0.29958 (8)	0.0525 (4)
H18	0.0324	0.7651	0.3096	0.063*
C6	0.11037 (13)	0.2693 (2)	0.33816 (8)	0.0497 (4)
C14	0.21927 (14)	0.3726 (2)	0.10374 (8)	0.0571 (5)
H14	0.2718	0.4041	0.1418	0.068*
C22	−0.14328 (14)	0.4854 (2)	0.22919 (8)	0.0573 (5)
H22	−0.1623	0.4166	0.1911	0.069*
C19	−0.08864 (14)	0.6860 (2)	0.34186 (8)	0.0555 (4)
H19	−0.0694	0.7540	0.3801	0.067*
C21	−0.20611 (14)	0.4773 (2)	0.27126 (9)	0.0605 (5)
H21	−0.2661	0.4042	0.2614	0.073*
C13	0.22975 (17)	0.4210 (3)	0.04357 (9)	0.0691 (5)
H13	0.2892	0.4854	0.0411	0.083*
C10	0.05400 (15)	0.2300 (3)	0.05051 (8)	0.0636 (5)
H10	−0.0056	0.1654	0.0526	0.076*
C11	0.06540 (18)	0.2783 (3)	−0.00952 (9)	0.0778 (6)
H11	0.0138	0.2456	−0.0478	0.093*
C1	0.19254 (16)	0.3679 (2)	0.37906 (9)	0.0640 (5)
H1	0.2497	0.4034	0.3645	0.077*
C5	0.02664 (15)	0.2143 (2)	0.36101 (9)	0.0631 (5)
H5	−0.0287	0.1467	0.3343	0.076*
C12	0.15271 (18)	0.3745 (3)	−0.01286 (10)	0.0766 (6)
H12	0.1598	0.4083	−0.0534	0.092*
C2	0.1902 (2)	0.4136 (3)	0.44110 (10)	0.0817 (6)
H2	0.2452	0.4814	0.4681	0.098*
C4	0.02563 (19)	0.2603 (3)	0.42367 (11)	0.0817 (6)
H4	−0.0306	0.2236	0.4389	0.098*
C3	0.1069 (2)	0.3595 (3)	0.46336 (11)	0.0888 (7)
H3	0.1057	0.3902	0.5054	0.107*
C23	−0.32829 (18)	0.4804 (4)	0.35991 (12)	0.1021 (8)
H23A	−0.3601	0.4964	0.3947	0.153*
H23B	−0.3112	0.3553	0.3570	0.153*
H23C	−0.3773	0.5184	0.3193	0.153*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N3	0.0484 (8)	0.0397 (7)	0.0433 (7)	−0.0014 (6)	0.0151 (6)	−0.0002 (6)
N1	0.0615 (9)	0.0468 (8)	0.0537 (8)	−0.0044 (6)	0.0198 (7)	0.0018 (6)
N2	0.0626 (9)	0.0452 (8)	0.0525 (8)	−0.0046 (6)	0.0193 (7)	−0.0023 (6)
C8	0.0441 (9)	0.0432 (9)	0.0466 (9)	−0.0005 (7)	0.0120 (7)	−0.0027 (7)
C7	0.0454 (9)	0.0445 (9)	0.0469 (9)	−0.0017 (7)	0.0136 (7)	0.0034 (7)
O1	0.0639 (8)	0.0946 (10)	0.0677 (8)	−0.0174 (7)	0.0292 (7)	−0.0047 (7)
C15	0.0585 (10)	0.0394 (8)	0.0501 (9)	−0.0040 (7)	0.0222 (8)	−0.0015 (7)
C16	0.0648 (11)	0.0426 (9)	0.0480 (10)	0.0041 (8)	0.0157 (8)	0.0041 (7)
C9	0.0542 (10)	0.0436 (9)	0.0447 (9)	0.0013 (7)	0.0148 (8)	−0.0022 (7)
C17	0.0535 (10)	0.0390 (8)	0.0473 (9)	0.0029 (7)	0.0118 (7)	0.0026 (7)
C20	0.0490 (10)	0.0554 (10)	0.0546 (10)	−0.0034 (8)	0.0149 (8)	0.0039 (8)
C18	0.0522 (10)	0.0466 (9)	0.0586 (10)	−0.0092 (7)	0.0159 (8)	−0.0038 (8)
C6	0.0599 (10)	0.0442 (9)	0.0468 (9)	0.0029 (8)	0.0181 (8)	0.0055 (7)
C14	0.0623 (11)	0.0607 (10)	0.0495 (10)	−0.0061 (9)	0.0183 (8)	−0.0045 (8)
C22	0.0621 (11)	0.0514 (10)	0.0539 (10)	−0.0074 (8)	0.0097 (9)	−0.0087 (8)
C19	0.0602 (11)	0.0559 (10)	0.0502 (10)	−0.0092 (8)	0.0159 (8)	−0.0068 (8)
C21	0.0538 (11)	0.0607 (11)	0.0636 (12)	−0.0142 (8)	0.0118 (9)	−0.0043 (9)
C13	0.0838 (14)	0.0710 (12)	0.0600 (12)	−0.0132 (10)	0.0328 (11)	−0.0016 (10)
C10	0.0651 (12)	0.0705 (12)	0.0527 (11)	−0.0093 (9)	0.0128 (9)	−0.0059 (9)
C11	0.0869 (15)	0.0935 (15)	0.0440 (11)	−0.0068 (13)	0.0049 (10)	−0.0029 (10)
C1	0.0781 (13)	0.0606 (11)	0.0509 (11)	−0.0097 (10)	0.0147 (9)	0.0028 (9)
C5	0.0696 (12)	0.0659 (11)	0.0586 (11)	0.0026 (9)	0.0262 (10)	0.0088 (9)
C12	0.1036 (17)	0.0800 (14)	0.0499 (12)	−0.0021 (13)	0.0283 (11)	0.0052 (10)
C2	0.1120 (18)	0.0747 (14)	0.0526 (12)	−0.0107 (12)	0.0145 (12)	−0.0038 (10)
C4	0.0977 (17)	0.0911 (15)	0.0706 (14)	0.0114 (13)	0.0469 (13)	0.0118 (13)
C3	0.136 (2)	0.0829 (15)	0.0526 (12)	0.0136 (15)	0.0356 (14)	0.0005 (11)
C23	0.0752 (15)	0.143 (2)	0.1000 (18)	−0.0381 (15)	0.0436 (13)	−0.0071 (16)

Geometric parameters (Å, º) top

N3—C8	1.3696 (19)	C14—C13	1.378 (2)
N3—C7	1.3697 (19)	C14—H14	0.9300
N3—C15	1.470 (2)	C22—C21	1.386 (2)
N1—C7	1.316 (2)	C22—H22	0.9300
N1—N2	1.3877 (19)	C19—H19	0.9300
N2—C8	1.312 (2)	C21—H21	0.9300
C8—C9	1.476 (2)	C13—C12	1.374 (3)
C7—C6	1.469 (2)	C13—H13	0.9300
O1—C20	1.3672 (19)	C10—C11	1.379 (3)
O1—C23	1.410 (2)	C10—H10	0.9300
C15—C16	1.514 (2)	C11—C12	1.370 (3)
C15—H15A	0.9700	C11—H11	0.9300
C15—H15B	0.9700	C1—C2	1.375 (3)
C16—C17	1.509 (2)	C1—H1	0.9300
C16—H16A	0.9700	C5—C4	1.383 (3)
C16—H16B	0.9700	C5—H5	0.9300
C9—C14	1.382 (2)	C12—H12	0.9300
C9—C10	1.389 (2)	C2—C3	1.373 (3)
C17—C22	1.376 (2)	C2—H2	0.9300
C17—C18	1.395 (2)	C4—C3	1.369 (3)
C20—C21	1.379 (2)	C4—H4	0.9300
C20—C19	1.384 (2)	C3—H3	0.9300
C18—C19	1.369 (2)	C23—H23A	0.9600
C18—H18	0.9300	C23—H23B	0.9600
C6—C1	1.384 (2)	C23—H23C	0.9600
C6—C5	1.388 (2)

C8—N3—C7	104.92 (13)	C17—C22—C21	122.31 (16)
C8—N3—C15	125.81 (12)	C17—C22—H22	118.8
C7—N3—C15	127.83 (12)	C21—C22—H22	118.8
C7—N1—N2	107.74 (12)	C18—C19—C20	120.23 (16)
C8—N2—N1	107.00 (12)	C18—C19—H19	119.9
N2—C8—N3	110.49 (13)	C20—C19—H19	119.9
N2—C8—C9	123.67 (14)	C20—C21—C22	119.31 (16)
N3—C8—C9	125.83 (14)	C20—C21—H21	120.3
N1—C7—N3	109.83 (14)	C22—C21—H21	120.3
N1—C7—C6	123.88 (14)	C12—C13—C14	120.27 (19)
N3—C7—C6	126.29 (14)	C12—C13—H13	119.9
C20—O1—C23	117.67 (15)	C14—C13—H13	119.9
N3—C15—C16	112.31 (13)	C11—C10—C9	120.37 (18)
N3—C15—H15A	109.1	C11—C10—H10	119.8
C16—C15—H15A	109.1	C9—C10—H10	119.8
N3—C15—H15B	109.1	C12—C11—C10	120.08 (18)
C16—C15—H15B	109.1	C12—C11—H11	120.0
H15A—C15—H15B	107.9	C10—C11—H11	120.0
C17—C16—C15	114.86 (13)	C2—C1—C6	120.38 (19)
C17—C16—H16A	108.6	C2—C1—H1	119.8
C15—C16—H16A	108.6	C6—C1—H1	119.8
C17—C16—H16B	108.6	C4—C5—C6	119.85 (19)
C15—C16—H16B	108.6	C4—C5—H5	120.1
H16A—C16—H16B	107.5	C6—C5—H5	120.1
C14—C9—C10	118.91 (15)	C11—C12—C13	120.04 (18)
C14—C9—C8	121.36 (14)	C11—C12—H12	120.0
C10—C9—C8	119.68 (15)	C13—C12—H12	120.0
C22—C17—C18	117.06 (15)	C3—C2—C1	120.2 (2)
C22—C17—C16	123.21 (15)	C3—C2—H2	119.9
C18—C17—C16	119.73 (15)	C1—C2—H2	119.9
O1—C20—C21	124.90 (16)	C3—C4—C5	120.4 (2)
O1—C20—C19	115.60 (15)	C3—C4—H4	119.8
C21—C20—C19	119.50 (16)	C5—C4—H4	119.8
C19—C18—C17	121.58 (15)	C4—C3—C2	120.0 (2)
C19—C18—H18	119.2	C4—C3—H3	120.0
C17—C18—H18	119.2	C2—C3—H3	120.0
C1—C6—C5	119.14 (16)	O1—C23—H23A	109.5
C1—C6—C7	121.75 (15)	O1—C23—H23B	109.5
C5—C6—C7	119.08 (16)	H23A—C23—H23B	109.5
C13—C14—C9	120.32 (17)	O1—C23—H23C	109.5
C13—C14—H14	119.8	H23A—C23—H23C	109.5
C9—C14—H14	119.8	H23B—C23—H23C	109.5

C7—N1—N2—C8	−0.02 (17)	N3—C7—C6—C1	−51.7 (2)
N1—N2—C8—N3	0.79 (17)	N1—C7—C6—C5	−50.6 (2)
N1—N2—C8—C9	179.40 (14)	N3—C7—C6—C5	130.15 (17)
C7—N3—C8—N2	−1.21 (17)	C10—C9—C14—C13	0.7 (3)
C15—N3—C8—N2	−168.36 (14)	C8—C9—C14—C13	178.24 (16)
C7—N3—C8—C9	−179.79 (14)	C18—C17—C22—C21	0.3 (2)
C15—N3—C8—C9	13.1 (2)	C16—C17—C22—C21	−179.53 (16)
N2—N1—C7—N3	−0.75 (17)	C17—C18—C19—C20	−0.2 (3)
N2—N1—C7—C6	179.89 (14)	O1—C20—C19—C18	−178.99 (15)
C8—N3—C7—N1	1.19 (17)	C21—C20—C19—C18	0.5 (3)
C15—N3—C7—N1	167.99 (14)	O1—C20—C21—C22	179.03 (16)
C8—N3—C7—C6	−179.46 (14)	C19—C20—C21—C22	−0.4 (3)
C15—N3—C7—C6	−12.7 (2)	C17—C22—C21—C20	0.0 (3)
C8—N3—C15—C16	78.47 (18)	C9—C14—C13—C12	−0.3 (3)
C7—N3—C15—C16	−85.73 (18)	C14—C9—C10—C11	−0.4 (3)
N3—C15—C16—C17	74.66 (17)	C8—C9—C10—C11	−177.97 (17)
N2—C8—C9—C14	−125.15 (18)	C9—C10—C11—C12	−0.4 (3)
N3—C8—C9—C14	53.2 (2)	C5—C6—C1—C2	−1.2 (3)
N2—C8—C9—C10	52.4 (2)	C7—C6—C1—C2	−179.33 (17)
N3—C8—C9—C10	−129.25 (18)	C1—C6—C5—C4	0.8 (3)
C15—C16—C17—C22	−113.57 (18)	C7—C6—C5—C4	178.96 (17)
C15—C16—C17—C18	66.60 (19)	C10—C11—C12—C13	0.8 (3)
C23—O1—C20—C21	−0.7 (3)	C14—C13—C12—C11	−0.5 (3)
C23—O1—C20—C19	178.77 (18)	C6—C1—C2—C3	1.0 (3)
C22—C17—C18—C19	−0.2 (2)	C6—C5—C4—C3	−0.1 (3)
C16—C17—C18—C19	179.62 (15)	C5—C4—C3—C2	−0.2 (3)
N1—C7—C6—C1	127.53 (18)	C1—C2—C3—C4	−0.3 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C16—H16A···N2ⁱ	0.97	2.62	3.542 (3)	160

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

Experimental details

Crystal data
Chemical formula	C₂₃H₂₁N₃O
M_r	355.43
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	293
a, b, c (Å)	13.144 (5), 7.411 (5), 21.333 (5)
β (°)	106.835 (5)
V (Å³)	1989.0 (16)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.07
Crystal size (mm)	0.30 × 0.20 × 0.20

Data collection
Diffractometer	Bruker Kappa APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 1999)
T_min, T_max	0.966, 0.991
No. of measured, independent and observed [I > 2σ(I)] reflections	17443, 3492, 2536
R_int	0.037
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.126, 1.03
No. of reflections	3492
No. of parameters	245
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.15, −0.12

Computer programs: APEX2 (Bruker, 2004), APEX2 and SAINT (Bruker, 2004), SAINT and XPREP (Bruker, 2004), SIR92 (Altomare et al., 1994), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009) and Mercury (Macrae et al., 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C16—H16A···N2ⁱ	0.97	2.62	3.542 (3)	160

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

Acknowledgements

VG thanks the UGC, India, for financial assistance under the Minor Research Project (2010–2011). The authors thank the Sophisticated Analytical Instrument Facility, IIT-Madras, Chennai-36, for the single-crystal X-ray data collection. DÜ and EB thank the Research Fund of Karadeniz Technical University for its support of this work.

References

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