3,4-Dimeth-oxy-N-((E)-4-{[1-(prop-2-en-1-yl)-1H-1,2,3-triazol-4-yl]meth-oxy}benzyl-idene)aniline.

In the title compound, C(21)H(22)N(4)O(3), the triazole ring is planar [maximum deviaton = 0.004 (1) Å] and makes dihedral angles of 26.21 (8) and 38.66 (8)° with the two benzene rings. In the crystal, mol-ecules are linked by C-H⋯O hydrogen bonds, forming zigzag chains along [1-11]. In addition, a weak C-H⋯π intreraction is also observed.

Related literature

For background on the importance of triazole derivatives and their uses, see: da Silva et al. (2011 ▶); Hranjec et al. (2011 ▶); Shi & Zhou (2011 ▶); Yap & Weinreb (2006 ▶); Yu et al. (2006 ▶).

Experimental

Crystal data

C21H22N4O3

M = 378.43

Triclinic,

a = 5.8144 (4) Å

b = 11.9677 (8) Å

c = 14.1019 (10) Å

α = 85.803 (6)°

β = 80.497 (6)°

γ = 80.434 (5)°

V = 953.30 (12) Å3

Z = 2

Mo Kα radiation

μ = 0.09 mm−1

T = 296 K

0.73 × 0.41 × 0.21 mm

Data collection

Stoe IPDS 2 diffractometer

Absorption correction: integration (X-RED32; Stoe & Cie, 2002 ▶) T min = 0.957, T max = 0.981

15258 measured reflections

3919 independent reflections

2795 reflections with I > 2σ(I)

R int = 0.050

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.107

S = 1.04

3919 reflections

253 parameters

H-atom parameters constrained

Δρmax = 0.14 e Å−3

Δρmin = −0.18 e Å−3

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 (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812026761/gk2500sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812026761/gk2500Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812026761/gk2500Isup3.cml

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

C21H22N4O3	Z = 2
Mr = 378.43	F(000) = 400
Triclinic, P1	Dx = 1.318 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.8144 (4) Å	Cell parameters from 16791 reflections
b = 11.9677 (8) Å	θ = 2.2–27.3°
c = 14.1019 (10) Å	µ = 0.09 mm−1
α = 85.803 (6)°	T = 296 K
β = 80.497 (6)°	Prism, brown
γ = 80.434 (5)°	0.73 × 0.41 × 0.21 mm
V = 953.30 (12) Å3

Stoe IPDS 2 diffractometer	3919 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus	2795 reflections with I > 2σ(I)
Plane graphite monochromator	Rint = 0.050
Detector resolution: 6.67 pixels mm-1	θmax = 26.5°, θmin = 2.2°
ω scans	h = −7→7
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	k = −15→15
Tmin = 0.957, Tmax = 0.981	l = −17→17
15258 measured reflections

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.107	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0603P)2] where P = (Fo2 + 2Fc2)/3
3919 reflections	(Δ/σ)max < 0.001
253 parameters	Δρmax = 0.14 e Å−3
0 restraints	Δρmin = −0.18 e Å−3

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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
O1	−0.04640 (19)	0.88296 (10)	0.07531 (10)	0.0725 (4)
O2	0.35022 (17)	0.75647 (9)	0.03759 (8)	0.0615 (4)
O3	0.67186 (18)	0.09568 (8)	0.56736 (8)	0.0618 (4)
N1	0.1657 (2)	0.50851 (10)	0.32214 (9)	0.0553 (4)
N2	1.0236 (2)	−0.14989 (10)	0.76913 (9)	0.0557 (4)
N3	0.7884 (2)	−0.14280 (12)	0.78848 (11)	0.0693 (5)
N4	0.6981 (2)	−0.05436 (12)	0.73864 (11)	0.0661 (5)
C1	0.1137 (2)	0.60697 (11)	0.26194 (11)	0.0503 (4)
C2	−0.1013 (2)	0.67614 (12)	0.28129 (11)	0.0561 (5)
C3	−0.1602 (3)	0.77029 (13)	0.22197 (12)	0.0581 (5)
C4	−0.0060 (2)	0.79558 (11)	0.14080 (11)	0.0526 (5)
C5	0.2124 (2)	0.72537 (11)	0.12021 (10)	0.0495 (4)
C6	0.2718 (2)	0.63275 (11)	0.17977 (11)	0.0508 (4)
C7	−0.2711 (3)	0.95187 (13)	0.08467 (16)	0.0732 (6)
C8	0.5684 (3)	0.68677 (14)	0.00812 (13)	0.0653 (6)
C9	0.3712 (3)	0.48356 (12)	0.34398 (11)	0.0537 (5)
C10	0.4505 (2)	0.38187 (12)	0.40066 (11)	0.0504 (4)
C11	0.6468 (2)	0.37782 (12)	0.44608 (12)	0.0554 (5)
C12	0.7232 (2)	0.28590 (12)	0.50323 (11)	0.0550 (5)
C13	0.6079 (2)	0.19201 (11)	0.51366 (11)	0.0497 (4)
C14	0.4171 (2)	0.19244 (12)	0.46571 (11)	0.0539 (5)
C15	0.3388 (2)	0.28612 (12)	0.41111 (11)	0.0534 (5)
C16	0.8385 (3)	0.10194 (13)	0.62971 (13)	0.0608 (5)
C17	0.8768 (2)	−0.00575 (12)	0.68750 (11)	0.0523 (4)
C18	1.0838 (2)	−0.06698 (12)	0.70649 (11)	0.0545 (5)
C19	1.1770 (3)	−0.23609 (13)	0.81922 (14)	0.0659 (6)
C20	1.1179 (3)	−0.35129 (13)	0.81555 (13)	0.0613 (5)
C21	1.1076 (3)	−0.42391 (14)	0.88837 (14)	0.0708 (6)
H2	−0.20840	0.65930	0.33500	0.0670*
H3	−0.30470	0.81690	0.23690	0.0700*
H6	0.41750	0.58680	0.16560	0.0610*
H7A	−0.30230	0.98770	0.14520	0.0880*
H7B	−0.38990	0.90580	0.08210	0.0880*
H7C	−0.27330	1.00890	0.03310	0.0880*
H8A	0.54070	0.61200	−0.00200	0.0780*
H8B	0.66660	0.68280	0.05710	0.0780*
H8C	0.64580	0.71830	−0.05080	0.0780*
H9	0.47820	0.53310	0.32260	0.0640*
H11	0.72860	0.43920	0.43750	0.0660*
H12	0.85140	0.28650	0.53480	0.0660*
H14	0.34230	0.12890	0.47070	0.0650*
H15	0.20890	0.28590	0.38050	0.0640*
H16A	0.78020	0.16410	0.67210	0.0730*
H16B	0.98690	0.11620	0.59190	0.0730*
H18	1.23550	−0.05380	0.68110	0.0650*
H19A	1.16170	−0.21710	0.88590	0.0790*
H19B	1.34010	−0.23560	0.79000	0.0790*
H20	1.08630	−0.37280	0.75750	0.0740*
H21A	1.13830	−0.40490	0.94730	0.0850*
H21B	1.06940	−0.49510	0.88170	0.0850*

	U11	U22	U33	U12	U13	U23
O1	0.0606 (6)	0.0700 (7)	0.0781 (8)	0.0077 (5)	−0.0144 (6)	0.0221 (6)
O2	0.0562 (6)	0.0660 (6)	0.0546 (7)	0.0023 (5)	−0.0065 (5)	0.0151 (5)
O3	0.0753 (7)	0.0498 (5)	0.0673 (7)	−0.0155 (5)	−0.0325 (6)	0.0124 (5)
N1	0.0600 (7)	0.0532 (6)	0.0553 (8)	−0.0148 (5)	−0.0159 (6)	0.0100 (6)
N2	0.0519 (7)	0.0592 (7)	0.0563 (8)	−0.0087 (5)	−0.0153 (6)	0.0104 (6)
N3	0.0569 (8)	0.0777 (9)	0.0704 (9)	−0.0128 (6)	−0.0112 (7)	0.0244 (7)
N4	0.0511 (7)	0.0728 (8)	0.0710 (9)	−0.0081 (6)	−0.0111 (6)	0.0185 (7)
C1	0.0548 (8)	0.0477 (7)	0.0528 (8)	−0.0149 (6)	−0.0180 (6)	0.0053 (6)
C2	0.0505 (8)	0.0608 (8)	0.0587 (9)	−0.0154 (7)	−0.0097 (7)	0.0033 (7)
C3	0.0459 (7)	0.0590 (8)	0.0685 (10)	−0.0034 (6)	−0.0123 (7)	−0.0003 (7)
C4	0.0514 (8)	0.0505 (7)	0.0571 (9)	−0.0059 (6)	−0.0183 (6)	0.0066 (7)
C5	0.0496 (7)	0.0528 (7)	0.0479 (8)	−0.0092 (6)	−0.0148 (6)	0.0040 (6)
C6	0.0493 (7)	0.0500 (7)	0.0538 (9)	−0.0045 (6)	−0.0158 (6)	0.0039 (6)
C7	0.0631 (10)	0.0586 (9)	0.0952 (14)	0.0050 (7)	−0.0242 (9)	0.0085 (9)
C8	0.0573 (9)	0.0723 (10)	0.0603 (10)	−0.0005 (7)	−0.0056 (7)	0.0072 (8)
C9	0.0585 (8)	0.0535 (8)	0.0524 (9)	−0.0174 (6)	−0.0138 (7)	0.0070 (6)
C10	0.0540 (8)	0.0515 (7)	0.0457 (8)	−0.0107 (6)	−0.0083 (6)	0.0052 (6)
C11	0.0584 (8)	0.0516 (7)	0.0599 (9)	−0.0183 (6)	−0.0156 (7)	0.0094 (7)
C12	0.0539 (8)	0.0539 (8)	0.0611 (9)	−0.0143 (6)	−0.0191 (7)	0.0072 (7)
C13	0.0539 (8)	0.0476 (7)	0.0478 (8)	−0.0083 (6)	−0.0112 (6)	0.0054 (6)
C14	0.0597 (8)	0.0498 (7)	0.0565 (9)	−0.0184 (6)	−0.0154 (7)	0.0062 (7)
C15	0.0536 (8)	0.0573 (8)	0.0529 (9)	−0.0147 (6)	−0.0167 (6)	0.0060 (7)
C16	0.0618 (9)	0.0590 (8)	0.0662 (10)	−0.0142 (7)	−0.0253 (7)	0.0123 (7)
C17	0.0522 (8)	0.0542 (7)	0.0512 (8)	−0.0095 (6)	−0.0124 (6)	0.0046 (6)
C18	0.0496 (8)	0.0582 (8)	0.0554 (9)	−0.0111 (6)	−0.0094 (6)	0.0083 (7)
C19	0.0655 (9)	0.0647 (9)	0.0701 (11)	−0.0091 (7)	−0.0285 (8)	0.0174 (8)
C20	0.0631 (9)	0.0614 (9)	0.0583 (10)	0.0010 (7)	−0.0173 (7)	−0.0014 (8)
C21	0.0779 (11)	0.0622 (9)	0.0745 (12)	−0.0105 (8)	−0.0244 (9)	0.0093 (9)

O1—C4	1.3603 (19)	C16—C17	1.478 (2)
O1—C7	1.416 (2)	C17—C18	1.3572 (18)
O2—C5	1.3658 (17)	C19—C20	1.482 (2)
O2—C8	1.415 (2)	C20—C21	1.296 (3)
O3—C13	1.3651 (17)	C2—H2	0.9300
O3—C16	1.426 (2)	C3—H3	0.9300
N1—C1	1.4215 (18)	C6—H6	0.9300
N1—C9	1.265 (2)	C7—H7A	0.9600
N2—N3	1.3392 (17)	C7—H7B	0.9600
N2—C18	1.3313 (19)	C7—H7C	0.9600
N2—C19	1.468 (2)	C8—H8A	0.9600
N3—N4	1.311 (2)	C8—H8B	0.9600
N4—C17	1.3528 (19)	C8—H8C	0.9600
C1—C2	1.3780 (18)	C9—H9	0.9300
C1—C6	1.405 (2)	C11—H11	0.9300
C2—C3	1.384 (2)	C12—H12	0.9300
C3—C4	1.381 (2)	C14—H14	0.9300
C4—C5	1.4008 (18)	C15—H15	0.9300
C5—C6	1.3732 (19)	C16—H16A	0.9700
C9—C10	1.458 (2)	C16—H16B	0.9700
C10—C11	1.3906 (18)	C18—H18	0.9300
C10—C15	1.3956 (19)	C19—H19A	0.9700
C11—C12	1.372 (2)	C19—H19B	0.9700
C12—C13	1.3883 (19)	C20—H20	0.9300
C13—C14	1.3904 (18)	C21—H21A	0.9300
C14—C15	1.370 (2)	C21—H21B	0.9300
C4—O1—C7	119.09 (13)	C4—C3—H3	120.00
C5—O2—C8	118.37 (12)	C1—C6—H6	120.00
C13—O3—C16	116.35 (11)	C5—C6—H6	120.00
C1—N1—C9	118.68 (12)	O1—C7—H7A	109.00
N3—N2—C18	110.57 (12)	O1—C7—H7B	109.00
N3—N2—C19	120.68 (13)	O1—C7—H7C	109.00
C18—N2—C19	128.62 (13)	H7A—C7—H7B	109.00
N2—N3—N4	107.23 (12)	H7A—C7—H7C	109.00
N3—N4—C17	108.59 (12)	H7B—C7—H7C	110.00
N1—C1—C2	119.65 (13)	O2—C8—H8A	109.00
N1—C1—C6	121.52 (11)	O2—C8—H8B	109.00
C2—C1—C6	118.75 (13)	O2—C8—H8C	109.00
C1—C2—C3	120.94 (14)	H8A—C8—H8B	110.00
C2—C3—C4	120.51 (14)	H8A—C8—H8C	109.00
O1—C4—C3	126.10 (13)	H8B—C8—H8C	109.00
O1—C4—C5	114.93 (13)	N1—C9—H9	118.00
C3—C4—C5	118.95 (13)	C10—C9—H9	118.00
O2—C5—C4	114.42 (12)	C10—C11—H11	119.00
O2—C5—C6	125.10 (12)	C12—C11—H11	119.00
C4—C5—C6	120.47 (13)	C11—C12—H12	120.00
C1—C6—C5	120.36 (12)	C13—C12—H12	120.00
N1—C9—C10	124.02 (14)	C13—C14—H14	120.00
C9—C10—C11	119.63 (13)	C15—C14—H14	120.00
C9—C10—C15	122.79 (13)	C10—C15—H15	119.00
C11—C10—C15	117.58 (13)	C14—C15—H15	119.00
C10—C11—C12	121.91 (13)	O3—C16—H16A	110.00
C11—C12—C13	119.56 (12)	O3—C16—H16B	110.00
O3—C13—C12	124.27 (12)	C17—C16—H16A	110.00
O3—C13—C14	116.29 (12)	C17—C16—H16B	110.00
C12—C13—C14	119.44 (13)	H16A—C16—H16B	108.00
C13—C14—C15	120.28 (12)	N2—C18—H18	127.00
C10—C15—C14	121.14 (12)	C17—C18—H18	127.00
O3—C16—C17	109.84 (12)	N2—C19—H19A	109.00
N4—C17—C16	123.06 (13)	N2—C19—H19B	109.00
N4—C17—C18	108.21 (13)	C20—C19—H19A	109.00
C16—C17—C18	128.49 (13)	C20—C19—H19B	109.00
N2—C18—C17	105.40 (12)	H19A—C19—H19B	108.00
N2—C19—C20	112.12 (14)	C19—C20—H20	118.00
C19—C20—C21	123.90 (17)	C21—C20—H20	118.00
C1—C2—H2	120.00	C20—C21—H21A	120.00
C3—C2—H2	120.00	C20—C21—H21B	120.00
C2—C3—H3	120.00	H21A—C21—H21B	120.00
C7—O1—C4—C5	173.80 (13)	C2—C3—C4—C5	−0.9 (2)
C7—O1—C4—C3	−4.8 (2)	O1—C4—C5—C6	−178.56 (12)
C8—O2—C5—C6	2.3 (2)	O1—C4—C5—O2	0.26 (17)
C8—O2—C5—C4	−176.48 (13)	C3—C4—C5—O2	178.94 (13)
C16—O3—C13—C12	12.0 (2)	C3—C4—C5—C6	0.1 (2)
C16—O3—C13—C14	−169.30 (13)	C4—C5—C6—C1	0.3 (2)
C13—O3—C16—C17	176.09 (12)	O2—C5—C6—C1	−178.40 (12)
C1—N1—C9—C10	−176.54 (14)	N1—C9—C10—C15	20.6 (2)
C9—N1—C1—C2	−139.67 (14)	N1—C9—C10—C11	−160.07 (15)
C9—N1—C1—C6	43.7 (2)	C9—C10—C15—C14	−179.39 (14)
C18—N2—N3—N4	−0.57 (17)	C9—C10—C11—C12	177.46 (14)
N3—N2—C19—C20	50.9 (2)	C11—C10—C15—C14	1.3 (2)
C18—N2—C19—C20	−133.53 (16)	C15—C10—C11—C12	−3.2 (2)
C19—N2—N3—N4	175.73 (14)	C10—C11—C12—C13	2.5 (2)
C19—N2—C18—C17	−175.21 (14)	C11—C12—C13—C14	0.2 (2)
N3—N2—C18—C17	0.71 (17)	C11—C12—C13—O3	178.86 (14)
N2—N3—N4—C17	0.19 (17)	C12—C13—C14—C15	−2.1 (2)
N3—N4—C17—C18	0.25 (18)	O3—C13—C14—C15	179.18 (13)
N3—N4—C17—C16	−174.51 (15)	C13—C14—C15—C10	1.3 (2)
C6—C1—C2—C3	−0.9 (2)	O3—C16—C17—N4	−51.4 (2)
C2—C1—C6—C5	0.1 (2)	O3—C16—C17—C18	134.98 (16)
N1—C1—C2—C3	−177.66 (13)	N4—C17—C18—N2	−0.58 (17)
N1—C1—C6—C5	176.80 (12)	C16—C17—C18—N2	173.81 (15)
C1—C2—C3—C4	1.3 (2)	N2—C19—C20—C21	−137.14 (18)
C2—C3—C4—O1	177.60 (14)

D—H···A	D—H	H···A	D···A	D—H···A
C19—H19A···O2i	0.97	2.54	3.385 (2)	146
C16—H16A···Cg2ii	0.97	2.87	3.6647 (18)	140

Table 1

Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the C1–C6 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C19—H19A⋯O2i	0.97	2.54	3.385 (2)	146
C16—H16A⋯Cg2ii	0.97	2.87	3.6647 (18)	140

Symmetry codes: (i) ; (ii) .