Literature DB >> 21582140

(E)-3-Allyl-sulfanyl-N-(4-methoxy-benzyl-idene)-5-(3,4,5-trimethoxy-phen-yl)-4H-1,2,4-triazol-4-amine.

Qian-Zhu Li, Bao-An Song, Song Yang, Yu-Guo Zheng, Qing-Qing Guo.

Abstract

The title compound, C(22)H(24)N(4)O(4)S, adopts a trans configuration with respect to the C=N double bond. A weak intra-molecular C-H⋯N hydrogen bond is observed between the N atom of the C=N double bond and its neighboring phenyl H atom. The crystal structure is stabilized by inter-molecular C-H⋯N hydrogen bonds and C-H⋯π inter-actions.

Entities: Chemical Disease Species

Year: 2009 PMID： 21582140 PMCID： PMC2968670 DOI： 10.1107/S1600536809002645

Source DB: PubMed Journal: Acta Crystallogr Sect E Struct Rep Online ISSN： 1600-5368

Related literature

For background on the biological activity of triazole compounds, see: Bekircan & Gumrukcuoglu (2005 ▶); Ewiss et al. (1986 ▶); Ikizler et al. (1998 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C22H24N4O4S M = 440.51 Monoclinic, a = 7.9414 (12) Å b = 15.043 (2) Å c = 19.047 (3) Å β = 100.385 (6)° V = 2238.1 (6) Å3 Z = 4 Mo Kα radiation μ = 0.18 mm−1 T = 293 (2) K 0.36 × 0.30 × 0.26 mm

Data collection

Bruker SMART CCD area-detector diffractometer Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.936, T max = 0.956 23323 measured reflections 3929 independent reflections 3354 reflections with I > 2σ(I) R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.035 wR(F 2) = 0.103 S = 1.07 3929 reflections 281 parameters H-atom parameters constrained Δρmax = 0.35 e Å−3 Δρmin = −0.20 e Å−3 Data collection: SMART (Bruker, 1997 ▶); cell refinement: SAINT (Bruker, 1997 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL. Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809002645/zl2154sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536809002645/zl2154Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C₂₂H₂₄N₄O₄S	F(000) = 928
M_r = 440.51	D_x = 1.307 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2895 reflections
a = 7.9414 (12) Å	θ = 2.4–27.9°
b = 15.043 (2) Å	µ = 0.18 mm⁻¹
c = 19.047 (3) Å	T = 293 K
β = 100.385 (6)°	Block, colorless
V = 2238.1 (6) Å³	0.36 × 0.30 × 0.26 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	3929 independent reflections
Radiation source: fine-focus sealed tube	3354 reflections with I > 2σ(I)
graphite	R_int = 0.028
φ and ω scans	θ_max = 25.0°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −8→9
T_min = 0.936, T_max = 0.956	k = −17→17
23323 measured reflections	l = −22→22

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)] = 0.035	H-atom parameters constrained
wR(F²) = 0.103	w = 1/[σ²(F_o²) + (0.0532P)² + 0.4889P] where P = (F_o² + 2F_c²)/3
S = 1.07	(Δ/σ)_max = 0.001
3929 reflections	Δρ_max = 0.35 e Å⁻³
281 parameters	Δρ_min = −0.20 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: 0.0132 (12)

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	U_iso*/U_eq
S1	−0.32086 (5)	0.40159 (3)	0.50696 (2)	0.05036 (16)
O2	0.53116 (15)	0.34899 (8)	0.80320 (6)	0.0566 (3)
O4	0.63039 (17)	0.63866 (9)	0.73084 (7)	0.0647 (4)
O1	0.27845 (18)	−0.05796 (9)	0.56221 (8)	0.0737 (4)
N4	0.04176 (16)	0.33704 (8)	0.60779 (7)	0.0419 (3)
N3	−0.00642 (16)	0.42733 (8)	0.59683 (7)	0.0392 (3)
O3	0.72831 (15)	0.49408 (9)	0.81168 (6)	0.0614 (4)
N2	−0.15075 (18)	0.54951 (9)	0.56327 (8)	0.0505 (4)
N1	0.00133 (18)	0.57222 (9)	0.60765 (8)	0.0493 (3)
C13	0.10497 (19)	0.20262 (10)	0.55230 (8)	0.0412 (4)
C3	0.5743 (2)	0.49373 (11)	0.76468 (8)	0.0461 (4)
C6	0.25403 (19)	0.49468 (10)	0.67595 (8)	0.0394 (3)
C12	0.05405 (19)	0.29577 (10)	0.55028 (8)	0.0426 (4)
H12	0.0303	0.3254	0.5068	0.051*
C14	0.1270 (2)	0.15253 (11)	0.61543 (9)	0.0464 (4)
H14	0.1020	0.1778	0.6569	0.056*
C8	−0.1542 (2)	0.46257 (10)	0.55731 (8)	0.0431 (4)
C7	0.0855 (2)	0.49833 (10)	0.62810 (8)	0.0398 (3)
C1	0.3077 (2)	0.41986 (10)	0.71705 (8)	0.0415 (4)
H1	0.2368	0.3704	0.7150	0.050*
C2	0.4679 (2)	0.41929 (11)	0.76131 (8)	0.0435 (4)
C5	0.3589 (2)	0.56949 (10)	0.67940 (8)	0.0443 (4)
H5	0.3221	0.6196	0.6524	0.053*
C4	0.5188 (2)	0.56862 (11)	0.72351 (9)	0.0463 (4)
C15	0.1852 (2)	0.06656 (11)	0.61640 (10)	0.0517 (4)
H15	0.2013	0.0342	0.6587	0.062*
C16	0.2205 (2)	0.02742 (11)	0.55411 (10)	0.0518 (4)
C18	0.1392 (2)	0.16211 (12)	0.49085 (9)	0.0517 (4)
H18	0.1234	0.1943	0.4485	0.062*
C10	−0.3730 (3)	0.30522 (14)	0.62529 (10)	0.0633 (5)
H10	−0.2735	0.3199	0.6569	0.076*
C9	−0.4510 (2)	0.37642 (12)	0.57463 (10)	0.0558 (4)
H9A	−0.4645	0.4300	0.6014	0.067*
H9B	−0.5639	0.3575	0.5511	0.067*
C19	0.4213 (3)	0.27423 (13)	0.80370 (12)	0.0717 (6)
H19A	0.4793	0.2294	0.8349	0.108*
H19B	0.3912	0.2507	0.7562	0.108*
H19C	0.3194	0.2922	0.8203	0.108*
C17	0.1965 (2)	0.07488 (12)	0.49092 (10)	0.0561 (5)
H17	0.2184	0.0488	0.4492	0.067*
C21	0.5991 (3)	0.70808 (15)	0.68073 (15)	0.0924 (8)
H21A	0.6853	0.7531	0.6925	0.139*
H21B	0.4884	0.7333	0.6816	0.139*
H21C	0.6021	0.6852	0.6339	0.139*
C11	−0.4301 (3)	0.22612 (15)	0.62922 (12)	0.0764 (6)
H11A	−0.5292	0.2083	0.5987	0.092*
H11B	−0.3724	0.1865	0.6626	0.092*
C20	0.8754 (3)	0.47977 (17)	0.78013 (13)	0.0797 (6)
H20A	0.9762	0.4808	0.8165	0.120*
H20B	0.8829	0.5258	0.7459	0.120*
H20C	0.8664	0.4231	0.7566	0.120*
C22	0.3150 (3)	−0.10321 (14)	0.50050 (15)	0.0858 (8)
H22A	0.3545	−0.1623	0.5135	0.129*
H22B	0.4019	−0.0714	0.4818	0.129*
H22C	0.2129	−0.1063	0.4648	0.129*

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0433 (3)	0.0626 (3)	0.0420 (3)	−0.00628 (19)	−0.00102 (17)	0.00451 (18)
O2	0.0536 (7)	0.0571 (7)	0.0529 (7)	−0.0027 (6)	−0.0065 (5)	0.0096 (6)
O4	0.0612 (8)	0.0609 (8)	0.0682 (8)	−0.0265 (6)	0.0013 (6)	−0.0029 (6)
O1	0.0718 (9)	0.0497 (7)	0.0989 (11)	0.0117 (6)	0.0139 (8)	−0.0119 (7)
N4	0.0437 (7)	0.0341 (7)	0.0443 (7)	−0.0016 (5)	−0.0015 (6)	0.0014 (5)
N3	0.0391 (7)	0.0357 (6)	0.0410 (7)	−0.0017 (5)	0.0026 (5)	0.0035 (5)
O3	0.0438 (7)	0.0890 (9)	0.0478 (7)	−0.0136 (6)	−0.0018 (5)	−0.0031 (6)
N2	0.0465 (8)	0.0451 (8)	0.0576 (9)	0.0013 (6)	0.0032 (6)	0.0085 (6)
N1	0.0475 (8)	0.0402 (7)	0.0582 (9)	−0.0013 (6)	0.0036 (7)	0.0031 (6)
C13	0.0378 (8)	0.0434 (8)	0.0413 (8)	−0.0037 (6)	0.0038 (6)	−0.0012 (7)
C3	0.0399 (9)	0.0610 (10)	0.0365 (8)	−0.0068 (7)	0.0046 (7)	−0.0069 (7)
C6	0.0382 (8)	0.0426 (8)	0.0378 (8)	−0.0028 (6)	0.0076 (6)	−0.0048 (6)
C12	0.0397 (8)	0.0447 (8)	0.0421 (9)	−0.0025 (7)	0.0042 (7)	0.0056 (7)
C14	0.0513 (9)	0.0446 (9)	0.0451 (9)	−0.0001 (7)	0.0137 (7)	0.0000 (7)
C8	0.0408 (9)	0.0453 (9)	0.0423 (9)	−0.0010 (7)	0.0045 (7)	0.0076 (7)
C7	0.0419 (8)	0.0371 (8)	0.0406 (8)	−0.0032 (6)	0.0083 (7)	0.0002 (6)
C1	0.0415 (8)	0.0427 (8)	0.0396 (8)	−0.0062 (6)	0.0056 (7)	−0.0025 (6)
C2	0.0440 (9)	0.0486 (9)	0.0376 (8)	0.0000 (7)	0.0063 (7)	−0.0020 (7)
C5	0.0493 (9)	0.0403 (8)	0.0434 (9)	−0.0051 (7)	0.0087 (7)	−0.0021 (7)
C4	0.0448 (9)	0.0505 (9)	0.0445 (9)	−0.0136 (7)	0.0101 (7)	−0.0086 (7)
C15	0.0523 (10)	0.0467 (9)	0.0575 (10)	0.0028 (8)	0.0141 (8)	0.0081 (8)
C16	0.0399 (9)	0.0437 (9)	0.0707 (12)	−0.0015 (7)	0.0068 (8)	−0.0087 (8)
C18	0.0538 (10)	0.0591 (10)	0.0404 (9)	−0.0002 (8)	0.0038 (7)	−0.0009 (7)
C10	0.0613 (12)	0.0763 (13)	0.0538 (11)	−0.0111 (10)	0.0142 (9)	−0.0017 (9)
C9	0.0467 (10)	0.0563 (10)	0.0668 (12)	−0.0027 (8)	0.0169 (9)	−0.0012 (9)
C19	0.0762 (14)	0.0586 (11)	0.0720 (13)	−0.0088 (10)	−0.0088 (10)	0.0201 (10)
C17	0.0496 (10)	0.0647 (11)	0.0531 (11)	0.0005 (8)	0.0068 (8)	−0.0199 (9)
C21	0.0758 (15)	0.0691 (14)	0.124 (2)	−0.0331 (12)	−0.0033 (14)	0.0223 (14)
C11	0.0755 (14)	0.0708 (14)	0.0833 (15)	0.0001 (11)	0.0154 (12)	0.0125 (11)
C20	0.0458 (11)	0.1008 (17)	0.0890 (16)	0.0021 (11)	0.0027 (11)	−0.0133 (13)
C22	0.0673 (14)	0.0626 (13)	0.128 (2)	0.0019 (10)	0.0205 (14)	−0.0384 (13)

S1—C8	1.7477 (16)	C1—H1	0.9300
S1—C9	1.8312 (18)	C5—C4	1.391 (2)
O2—C2	1.3649 (19)	C5—H5	0.9300
O2—C19	1.424 (2)	C15—C16	1.397 (2)
O4—C4	1.3676 (19)	C15—H15	0.9300
O4—C21	1.406 (3)	C16—C17	1.383 (3)
O1—C16	1.364 (2)	C18—C17	1.389 (2)
O1—C22	1.433 (3)	C18—H18	0.9300
N4—C12	1.278 (2)	C10—C11	1.280 (3)
N4—N3	1.4164 (17)	C10—C9	1.499 (3)
N3—C7	1.3681 (19)	C10—H10	0.9300
N3—C8	1.3810 (19)	C9—H9A	0.9700
O3—C3	1.3795 (19)	C9—H9B	0.9700
O3—C20	1.423 (2)	C19—H19A	0.9600
N2—C8	1.313 (2)	C19—H19B	0.9600
N2—N1	1.3863 (19)	C19—H19C	0.9600
N1—C7	1.319 (2)	C17—H17	0.9300
C13—C18	1.389 (2)	C21—H21A	0.9600
C13—C14	1.403 (2)	C21—H21B	0.9600
C13—C12	1.457 (2)	C21—H21C	0.9600
C3—C2	1.397 (2)	C11—H11A	0.9300
C3—C4	1.398 (2)	C11—H11B	0.9300
C6—C1	1.393 (2)	C20—H20A	0.9600
C6—C5	1.394 (2)	C20—H20B	0.9600
C6—C7	1.478 (2)	C20—H20C	0.9600
C12—H12	0.9300	C22—H22A	0.9600
C14—C15	1.372 (2)	C22—H22B	0.9600
C14—H14	0.9300	C22—H22C	0.9600
C1—C2	1.394 (2)

C8—S1—C9	100.95 (8)	C16—C15—H15	119.9
C2—O2—C19	117.02 (13)	O1—C16—C17	125.13 (17)
C4—O4—C21	118.08 (15)	O1—C16—C15	114.57 (17)
C16—O1—C22	117.95 (17)	C17—C16—C15	120.29 (16)
C12—N4—N3	113.56 (12)	C17—C18—C13	121.84 (16)
C7—N3—C8	105.79 (12)	C17—C18—H18	119.1
C7—N3—N4	125.15 (12)	C13—C18—H18	119.1
C8—N3—N4	128.97 (12)	C11—C10—C9	126.3 (2)
C3—O3—C20	115.13 (14)	C11—C10—H10	116.8
C8—N2—N1	107.50 (13)	C9—C10—H10	116.8
C7—N1—N2	108.17 (13)	C10—C9—S1	112.37 (13)
C18—C13—C14	118.26 (15)	C10—C9—H9A	109.1
C18—C13—C12	119.68 (14)	S1—C9—H9A	109.1
C14—C13—C12	122.03 (14)	C10—C9—H9B	109.1
O3—C3—C2	119.41 (15)	S1—C9—H9B	109.1
O3—C3—C4	120.93 (15)	H9A—C9—H9B	107.9
C2—C3—C4	119.56 (15)	O2—C19—H19A	109.5
C1—C6—C5	120.38 (15)	O2—C19—H19B	109.5
C1—C6—C7	121.86 (13)	H19A—C19—H19B	109.5
C5—C6—C7	117.75 (14)	O2—C19—H19C	109.5
N4—C12—C13	120.54 (14)	H19A—C19—H19C	109.5
N4—C12—H12	119.7	H19B—C19—H19C	109.5
C13—C12—H12	119.7	C16—C17—C18	118.84 (16)
C15—C14—C13	120.48 (15)	C16—C17—H17	120.6
C15—C14—H14	119.8	C18—C17—H17	120.6
C13—C14—H14	119.8	O4—C21—H21A	109.5
N2—C8—N3	109.43 (13)	O4—C21—H21B	109.5
N2—C8—S1	124.92 (12)	H21A—C21—H21B	109.5
N3—C8—S1	125.65 (12)	O4—C21—H21C	109.5
N1—C7—N3	109.08 (14)	H21A—C21—H21C	109.5
N1—C7—C6	124.59 (14)	H21B—C21—H21C	109.5
N3—C7—C6	126.32 (13)	C10—C11—H11A	120.0
C6—C1—C2	119.90 (14)	C10—C11—H11B	120.0
C6—C1—H1	120.1	H11A—C11—H11B	120.0
C2—C1—H1	120.1	O3—C20—H20A	109.5
O2—C2—C1	123.92 (14)	O3—C20—H20B	109.5
O2—C2—C3	115.99 (14)	H20A—C20—H20B	109.5
C1—C2—C3	120.09 (15)	O3—C20—H20C	109.5
C4—C5—C6	119.56 (15)	H20A—C20—H20C	109.5
C4—C5—H5	120.2	H20B—C20—H20C	109.5
C6—C5—H5	120.2	O1—C22—H22A	109.5
O4—C4—C5	123.97 (16)	O1—C22—H22B	109.5
O4—C4—C3	115.52 (15)	H22A—C22—H22B	109.5
C5—C4—C3	120.51 (14)	O1—C22—H22C	109.5
C14—C15—C16	120.28 (16)	H22A—C22—H22C	109.5
C14—C15—H15	119.9	H22B—C22—H22C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···N4	0.93	2.38	2.960 (2)	120
C12—H12···N2ⁱ	0.93	2.59	3.359 (2)	141
C19—H19A···N1ⁱⁱ	0.96	2.60	3.477 (3)	152
C9—H9A···Cg1ⁱⁱⁱ	0.97	2.79	3.616 (2)	143
C11—H11A···Cg2^iv	0.93	2.83	3.703 (2)	158
C15—H15···Cg1^v	0.93	2.70	3.514 (2)	147
C22—H22C···Cg2^vi	0.96	2.94	3.747 (2)	143

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C1–C6 and C13–C18 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1⋯N4	0.93	2.38	2.960 (2)	120
C12—H12⋯N2ⁱ	0.93	2.59	3.359 (2)	141
C19—H19A⋯N1ⁱⁱ	0.96	2.60	3.477 (3)	152
C9—H9A⋯Cg1ⁱⁱⁱ	0.97	2.79	3.616 (2)	143
C11—H11A⋯Cg2^iv	0.93	2.83	3.703 (2)	158
C15—H15⋯Cg1^v	0.93	2.70	3.514 (2)	147
C22—H22C⋯Cg2^vi	0.96	2.94	3.747 (2)	143

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) ; (vi) .

2 in total

1. A short history of SHELX.

Authors: George M Sheldrick
Journal: Acta Crystallogr A Date: 2007-12-21 Impact factor: 2.290

2. Synthesis and biological activities of some 4,5-dihydro-1H-1,2,4-triazol-5-one derivatives.

Authors: A A Ikizler; A Demirbas; C B Johansson; C Celik; M Serdar; H Yuksek
Journal: Acta Pol Pharm Date: 1998 Mar-Apr Impact factor: 0.330

2 in total