4-(4-Meth-oxy-pheneth-yl)-3,5-diphenyl-4H-1,2,4-triazole.

In the title compound, C(23)H(21)N(3)O, 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, mol-ecules are linked by weak C-H⋯N inter-actions, 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 = 355.43

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.126

S = 1.03

3492 reflections

245 parameters

H-atom parameters constrained

Δρmax = 0.15 e Å−3

Δρmin = −0.12 e Å−3

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.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812000359/su2362sup1.cif

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

Supplementary material file. DOI: 10.1107/S1600536812000359/su2362Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C23H21N3O	F(000) = 752
Mr = 355.43	Dx = 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

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

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(Fo2) + (0.0695P)2 + 0.175P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max < 0.001
3492 reflections	Δρmax = 0.15 e Å−3
245 parameters	Δρmin = −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)

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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

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) .