4-(1-Methyl-eth-yl)-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(22)H(24)N(4)O, the terminal and central benzene rings make dihedral angles of 52.7 (3) and 43.8 (2)°, respectively, with the triazole ring. The dihedral angle between the benzene rings is 8.9 (2)°. The crystal structure features C-H⋯π inter-actions. The atoms of the terminal propenyl group are disordered over two sets of sites, with a refined occupancy ratio of 0.714 (14):0.286 (14).

Related literature

For bond-length data, see: Allen et al. (1987 ▶). For general background to the properties of Schiff bases, see: Ajello & Cusmanos (1940 ▶); Dhar & Taploo (1982 ▶); Holla et al. (2005 ▶); Singh et al. (2012 ▶); Supuran et al. (1996 ▶).

Experimental

Crystal data

C22H24N4O

M = 360.45

Monoclinic,

a = 5.5885 (11) Å

b = 8.3929 (18) Å

c = 42.069 (9) Å

β = 92.149 (10)°

V = 1971.8 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 296 K

0.30 × 0.20 × 0.18 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.982, T max = 0.986

13866 measured reflections

3451 independent reflections

1259 reflections with I > 2σ(I)

R int = 0.082

Refinement

R[F 2 > 2σ(F 2)] = 0.068

wR(F 2) = 0.217

S = 0.96

3451 reflections

256 parameters

7 restraints

H-atom parameters constrained

Δρmax = 0.20 e Å−3

Δρmin = −0.20 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; 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, 2012 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶) and PLATON.

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813000755/bq2382sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813000755/bq2382Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813000755/bq2382Isup3.cml

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

C22H24N4O	F(000) = 768
Mr = 360.45	Dx = 1.214 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 219 reflections
a = 5.5885 (11) Å	θ = 3.5–21.5°
b = 8.3929 (18) Å	µ = 0.08 mm−1
c = 42.069 (9) Å	T = 296 K
β = 92.149 (10)°	Prism, colorless
V = 1971.8 (7) Å3	0.30 × 0.20 × 0.18 mm
Z = 4

Bruker Kappa APEXII CCD diffractometer	3451 independent reflections
Radiation source: fine-focus sealed tube	1259 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.082
ω scans	θmax = 25.0°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −6→4
Tmin = 0.982, Tmax = 0.986	k = −9→9
13866 measured reflections	l = −49→49

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)] = 0.068	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.217	H-atom parameters constrained
S = 0.96	w = 1/[σ2(Fo2) + (0.0893P)2] where P = (Fo2 + 2Fc2)/3
3451 reflections	(Δ/σ)max < 0.001
256 parameters	Δρmax = 0.20 e Å−3
7 restraints	Δρmin = −0.20 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	Occ. (<1)
O1	0.6921 (5)	0.1556 (4)	0.35472 (7)	0.0741 (14)
N1	0.0796 (6)	0.1766 (4)	0.22415 (8)	0.0634 (14)
N2	0.7693 (6)	0.0586 (5)	0.41985 (9)	0.0879 (18)
N3	0.8731 (6)	0.0688 (6)	0.44832 (9)	0.0939 (18)
N4	1.1055 (6)	0.0885 (5)	0.44413 (9)	0.0762 (16)
C1	−0.0186 (7)	0.1560 (5)	0.19307 (10)	0.0581 (17)
C2	−0.2092 (7)	0.2503 (6)	0.18440 (11)	0.0708 (19)
C3	−0.3158 (8)	0.2422 (6)	0.15464 (12)	0.084 (2)
C4	−0.2360 (8)	0.1385 (6)	0.13217 (11)	0.0717 (19)
C5	−0.0502 (9)	0.0411 (6)	0.14117 (11)	0.0805 (19)
C6	0.0617 (7)	0.0478 (6)	0.17103 (11)	0.0763 (19)
C7	−0.3528 (10)	0.1319 (8)	0.09917 (12)	0.106 (3)
C8	−0.1850 (11)	0.1621 (7)	0.07339 (12)	0.137 (3)
C9	−0.4985 (10)	−0.0154 (8)	0.09435 (12)	0.132 (3)
C10	0.2749 (8)	0.1146 (5)	0.23238 (10)	0.0681 (19)
C11	0.3876 (7)	0.1292 (5)	0.26388 (10)	0.0577 (17)
C12	0.2894 (7)	0.2200 (5)	0.28752 (10)	0.0633 (17)
C13	0.3977 (7)	0.2279 (5)	0.31714 (10)	0.0653 (19)
C14	0.6026 (7)	0.1427 (5)	0.32409 (10)	0.0578 (17)
C15	0.7072 (7)	0.0562 (5)	0.30096 (10)	0.0638 (17)
C16	0.5967 (8)	0.0500 (5)	0.27125 (10)	0.0683 (19)
C17	0.8850 (7)	0.0529 (6)	0.36388 (9)	0.0683 (19)
C18	0.9390 (7)	0.0723 (5)	0.39809 (10)	0.0618 (18)
C19	1.1516 (7)	0.0906 (5)	0.41344 (10)	0.0684 (19)
C20A	1.2557 (18)	0.0919 (15)	0.4733 (2)	0.083 (3)	0.714 (14)
C21A	1.251 (2)	0.254 (2)	0.4850 (4)	0.138 (7)	0.714 (14)
C22A	1.272 (2)	0.3163 (18)	0.5105 (3)	0.203 (8)	0.714 (14)
C21B	1.341 (6)	0.263 (6)	0.4899 (12)	0.138 (7)	0.286 (14)
C22B	1.120 (5)	0.342 (4)	0.4916 (8)	0.203 (8)	0.286 (14)
C20B	1.318 (4)	0.118 (5)	0.4674 (6)	0.083 (3)	0.286 (14)
H2	−0.26800	0.32180	0.19910	0.0850*
H3	−0.44500	0.30850	0.14950	0.1010*
H8A	−0.08690	0.25270	0.07880	0.2060*
H8B	−0.27430	0.18290	0.05390	0.2060*
H8C	−0.08510	0.07040	0.07080	0.2060*
H9A	−0.39530	−0.10690	0.09540	0.1980*
H5	0.00360	−0.03290	0.12660	0.0970*
H6	0.18930	−0.01960	0.17620	0.0910*
H7	−0.46740	0.22030	0.09820	0.1270*
H12	0.14840	0.27620	0.28320	0.0760*
H13	0.33210	0.29140	0.33270	0.0790*
H15	0.85030	0.00240	0.30520	0.0760*
H16	0.66660	−0.01020	0.25550	0.0820*
H17A	1.02500	0.07910	0.35200	0.0820*
H17B	0.84150	−0.05690	0.35930	0.0820*
H19	1.30020	0.10220	0.40450	0.0820*
H20A	1.19370	0.01930	0.48890	0.1000*	0.714 (14)
H20B	1.41820	0.06050	0.46890	0.1000*	0.714 (14)
H21A	1.22690	0.32730	0.46860	0.1660*	0.714 (14)
H22A	1.29690	0.25460	0.52870	0.2430*	0.714 (14)
H22B	1.26220	0.42660	0.51220	0.2430*	0.714 (14)
H9B	−0.58050	−0.01150	0.07390	0.1980*
H9C	−0.61350	−0.02290	0.11070	0.1980*
H10	0.35350	0.05510	0.21730	0.0820*
H20C	1.45990	0.11910	0.45480	0.1000*	0.286 (14)
H20D	1.33110	0.02440	0.48090	0.1000*	0.286 (14)
H21B	1.48080	0.29430	0.50080	0.1660*	0.286 (14)
H22C	0.98690	0.30480	0.48000	0.2430*	0.286 (14)
H22D	1.10720	0.43250	0.50430	0.2430*	0.286 (14)

	U11	U22	U33	U12	U13	U23
O1	0.077 (2)	0.081 (3)	0.063 (2)	0.0161 (18)	−0.0145 (16)	−0.0069 (16)
N1	0.057 (2)	0.072 (3)	0.061 (2)	0.001 (2)	−0.0013 (19)	0.0060 (19)
N2	0.047 (2)	0.146 (4)	0.070 (3)	0.000 (2)	−0.005 (2)	0.016 (3)
N3	0.052 (2)	0.159 (4)	0.071 (3)	0.003 (3)	0.005 (2)	0.020 (3)
N4	0.049 (2)	0.111 (3)	0.068 (3)	0.002 (2)	−0.007 (2)	0.001 (2)
C1	0.054 (3)	0.066 (3)	0.054 (3)	−0.010 (3)	−0.001 (2)	0.004 (2)
C2	0.056 (3)	0.081 (4)	0.075 (3)	0.009 (3)	−0.004 (2)	−0.013 (3)
C3	0.071 (3)	0.096 (4)	0.084 (4)	0.023 (3)	−0.014 (3)	−0.009 (3)
C4	0.068 (3)	0.080 (4)	0.066 (3)	−0.004 (3)	−0.011 (3)	0.008 (3)
C5	0.078 (3)	0.092 (4)	0.071 (3)	0.008 (3)	−0.002 (3)	−0.014 (3)
C6	0.073 (3)	0.085 (4)	0.070 (3)	0.015 (3)	−0.009 (3)	−0.006 (3)
C7	0.112 (4)	0.122 (6)	0.082 (4)	−0.003 (4)	−0.022 (4)	−0.004 (3)
C8	0.184 (6)	0.154 (6)	0.073 (4)	−0.071 (5)	−0.010 (4)	0.010 (4)
C9	0.112 (4)	0.187 (7)	0.096 (4)	−0.044 (5)	−0.020 (3)	−0.008 (4)
C10	0.069 (3)	0.076 (4)	0.059 (3)	0.001 (3)	0.000 (2)	−0.003 (2)
C11	0.052 (3)	0.067 (3)	0.054 (3)	−0.002 (2)	−0.001 (2)	0.006 (2)
C12	0.059 (3)	0.072 (3)	0.059 (3)	0.010 (2)	0.002 (2)	0.008 (3)
C13	0.066 (3)	0.070 (4)	0.060 (3)	0.008 (3)	0.002 (2)	0.002 (2)
C14	0.056 (3)	0.061 (3)	0.056 (3)	−0.003 (2)	−0.004 (2)	0.005 (2)
C15	0.054 (3)	0.069 (3)	0.068 (3)	0.009 (2)	−0.002 (2)	−0.005 (3)
C16	0.068 (3)	0.075 (4)	0.062 (3)	0.004 (3)	0.003 (2)	−0.011 (3)
C17	0.053 (3)	0.077 (4)	0.074 (3)	0.001 (3)	−0.011 (2)	−0.002 (3)
C18	0.045 (2)	0.080 (4)	0.060 (3)	0.001 (2)	−0.005 (2)	0.005 (3)
C19	0.051 (3)	0.091 (4)	0.063 (3)	−0.009 (3)	−0.001 (2)	0.000 (3)
C20A	0.044 (5)	0.140 (7)	0.065 (5)	−0.006 (5)	0.002 (4)	0.014 (5)
C21A	0.142 (16)	0.172 (9)	0.094 (10)	0.010 (11)	−0.082 (8)	−0.019 (7)
C22A	0.227 (14)	0.216 (13)	0.158 (13)	0.046 (10)	−0.088 (10)	−0.053 (10)
C21B	0.142 (16)	0.172 (9)	0.094 (10)	0.010 (11)	−0.082 (8)	−0.019 (7)
C22B	0.227 (14)	0.216 (13)	0.158 (13)	0.046 (10)	−0.088 (10)	−0.053 (10)
C20B	0.044 (5)	0.140 (7)	0.065 (5)	−0.006 (5)	0.002 (4)	0.014 (5)

O1—C14	1.369 (5)	C21B—C22B	1.41 (5)
O1—C17	1.422 (5)	C2—H2	0.9300
N1—C1	1.410 (5)	C3—H3	0.9300
N1—C10	1.246 (6)	C5—H5	0.9300
N2—N3	1.314 (5)	C6—H6	0.9300
N2—C18	1.348 (5)	C7—H7	0.9800
N3—N4	1.328 (5)	C8—H8A	0.9600
N4—C19	1.326 (6)	C8—H8B	0.9600
N4—C20A	1.461 (10)	C8—H8C	0.9600
N4—C20B	1.53 (2)	C9—H9A	0.9600
C1—C2	1.366 (6)	C9—H9B	0.9600
C1—C6	1.385 (6)	C9—H9C	0.9600
C2—C3	1.368 (7)	C10—H10	0.9300
C3—C4	1.372 (7)	C12—H12	0.9300
C4—C5	1.364 (7)	C13—H13	0.9300
C4—C7	1.513 (7)	C15—H15	0.9300
C5—C6	1.383 (7)	C16—H16	0.9300
C7—C8	1.482 (8)	C17—H17A	0.9700
C7—C9	1.490 (9)	C17—H17B	0.9700
C10—C11	1.451 (6)	C19—H19	0.9300
C11—C12	1.383 (6)	C20A—H20A	0.9700
C11—C16	1.370 (6)	C20A—H20B	0.9700
C12—C13	1.366 (6)	C20B—H20C	0.9700
C13—C14	1.372 (6)	C20B—H20D	0.9700
C14—C15	1.363 (6)	C21A—H21A	0.9300
C15—C16	1.374 (6)	C21B—H21B	0.9300
C17—C18	1.468 (6)	C22A—H22A	0.9300
C18—C19	1.340 (6)	C22A—H22B	0.9300
C20A—C21A	1.45 (2)	C22B—H22C	0.9300
C20B—C21B	1.54 (6)	C22B—H22D	0.9300
C21A—C22A	1.20 (2)
C14—O1—C17	117.0 (3)	C8—C7—H7	106.00
C1—N1—C10	120.9 (4)	C9—C7—H7	106.00
N3—N2—C18	108.4 (3)	C7—C8—H8A	109.00
N2—N3—N4	106.7 (3)	C7—C8—H8B	109.00
N3—N4—C19	111.0 (3)	C7—C8—H8C	109.00
N3—N4—C20A	115.2 (5)	H8A—C8—H8B	109.00
N3—N4—C20B	132.4 (9)	H8A—C8—H8C	109.00
C19—N4—C20A	133.7 (5)	H8B—C8—H8C	110.00
C19—N4—C20B	116.5 (9)	C7—C9—H9A	109.00
N1—C1—C2	116.7 (4)	C7—C9—H9B	109.00
N1—C1—C6	125.2 (4)	C7—C9—H9C	109.00
C2—C1—C6	118.1 (4)	H9A—C9—H9B	110.00
C1—C2—C3	121.6 (4)	H9A—C9—H9C	109.00
C2—C3—C4	121.4 (4)	H9B—C9—H9C	110.00
C3—C4—C5	116.9 (4)	N1—C10—H10	118.00
C3—C4—C7	121.0 (4)	C11—C10—H10	118.00
C5—C4—C7	122.1 (5)	C11—C12—H12	120.00
C4—C5—C6	122.8 (4)	C13—C12—H12	120.00
C1—C6—C5	119.2 (4)	C12—C13—H13	120.00
C4—C7—C8	113.7 (5)	C14—C13—H13	120.00
C4—C7—C9	111.7 (5)	C14—C15—H15	121.00
C8—C7—C9	113.6 (5)	C16—C15—H15	121.00
N1—C10—C11	124.3 (4)	C11—C16—H16	119.00
C10—C11—C12	122.2 (4)	C15—C16—H16	119.00
C10—C11—C16	120.2 (4)	O1—C17—H17A	110.00
C12—C11—C16	117.6 (4)	O1—C17—H17B	110.00
C11—C12—C13	120.6 (4)	C18—C17—H17A	110.00
C12—C13—C14	120.4 (4)	C18—C17—H17B	110.00
O1—C14—C13	115.6 (4)	H17A—C17—H17B	108.00
O1—C14—C15	124.2 (4)	N4—C19—H19	127.00
C13—C14—C15	120.2 (4)	C18—C19—H19	127.00
C14—C15—C16	118.6 (4)	N4—C20A—H20A	110.00
C11—C16—C15	122.5 (4)	N4—C20A—H20B	110.00
O1—C17—C18	108.9 (3)	C21A—C20A—H20A	110.00
N2—C18—C17	122.2 (4)	C21A—C20A—H20B	110.00
N2—C18—C19	108.4 (4)	H20A—C20A—H20B	109.00
C17—C18—C19	129.1 (4)	C21B—C20B—H20C	106.00
N4—C19—C18	105.5 (4)	C21B—C20B—H20D	106.00
N4—C20A—C21A	106.7 (10)	H20C—C20B—H20D	106.00
N4—C20B—C21B	124 (3)	N4—C20B—H20D	106.00
C20A—C21A—C22A	135.6 (16)	N4—C20B—H20C	106.00
C20B—C21B—C22B	111 (3)	C20A—C21A—H21A	112.00
C1—C2—H2	119.00	C22A—C21A—H21A	113.00
C3—C2—H2	119.00	C20B—C21B—H21B	125.00
C2—C3—H3	119.00	C22B—C21B—H21B	124.00
C4—C3—H3	119.00	C21A—C22A—H22A	120.00
C4—C5—H5	119.00	C21A—C22A—H22B	120.00
C6—C5—H5	119.00	H22A—C22A—H22B	120.00
C1—C6—H6	120.00	C21B—C22B—H22C	120.00
C5—C6—H6	120.00	C21B—C22B—H22D	120.00
C4—C7—H7	106.00	H22C—C22B—H22D	120.00
C17—O1—C14—C15	−10.0 (6)	C5—C4—C7—C9	71.5 (6)
C17—O1—C14—C13	171.9 (4)	C3—C4—C7—C9	−107.5 (6)
C14—O1—C17—C18	−174.2 (3)	C7—C4—C5—C6	178.7 (5)
C1—N1—C10—C11	−179.7 (4)	C5—C4—C7—C8	−58.6 (7)
C10—N1—C1—C6	11.9 (6)	C3—C4—C7—C8	122.3 (6)
C10—N1—C1—C2	−168.6 (4)	C4—C5—C6—C1	0.9 (7)
N3—N2—C18—C19	0.3 (5)	N1—C10—C11—C16	176.6 (4)
C18—N2—N3—N4	−0.1 (5)	N1—C10—C11—C12	−2.5 (7)
N3—N2—C18—C17	174.9 (4)	C10—C11—C16—C15	−178.2 (4)
N2—N3—N4—C20A	−176.1 (6)	C10—C11—C12—C13	178.4 (4)
N2—N3—N4—C19	−0.2 (6)	C12—C11—C16—C15	1.0 (6)
N3—N4—C20A—C21A	−84.7 (9)	C16—C11—C12—C13	−0.7 (6)
N3—N4—C19—C18	0.3 (5)	C11—C12—C13—C14	−1.6 (6)
C20A—N4—C19—C18	175.2 (8)	C12—C13—C14—C15	3.6 (6)
C19—N4—C20A—C21A	100.6 (9)	C12—C13—C14—O1	−178.1 (4)
N1—C1—C6—C5	−179.4 (4)	C13—C14—C15—C16	−3.3 (6)
C2—C1—C6—C5	1.1 (7)	O1—C14—C15—C16	178.6 (4)
N1—C1—C2—C3	178.9 (4)	C14—C15—C16—C11	1.0 (6)
C6—C1—C2—C3	−1.6 (7)	O1—C17—C18—N2	53.0 (6)
C1—C2—C3—C4	0.1 (7)	O1—C17—C18—C19	−133.6 (5)
C2—C3—C4—C7	−179.2 (5)	N2—C18—C19—N4	−0.4 (5)
C2—C3—C4—C5	1.8 (7)	C17—C18—C19—N4	−174.5 (4)
C3—C4—C5—C6	−2.3 (7)	N4—C20A—C21A—C22A	151.9 (14)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···Cg3i	0.93	2.96	3.752 (5)	144
C8—H8A···Cg1ii	0.96	2.80	3.678 (6)	153

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg3 are the centroids of the N2–N4/C18/C19 1H-1,2,3-triazole and C11–C16 benzene rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯Cg3i	0.93	2.96	3.752 (5)	144
C8—H8A⋯Cg1ii	0.96	2.80	3.678 (6)	153

Symmetry codes: (i) ; (ii) .