(E)-4-({[4-(Benzo[d]thia­zol-2-yl)phen­yl]imino}­meth­yl)-N,N-di­ethyl­aniline

Yao, S.; Zhang, X.

doi:10.1107/S2414314616016217

organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 1| Part 10| October 2016| x161621

https://doi.org/10.1107/S2414314616016217

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(E)-4-({[4-(Benzo[d]thiazol-2-yl)phenyl]imino}methyl)-N,N-diethylaniline

Shun Yao ^a and Xin Zhang ^a ^*

^aDepartment of Chemistry, Anhui University, Hefei 230601, Peoples Republic of China and, Key Laboratory of Functional Inorganic Materials, Chemistry, Hefei 230601, People's Republic of China
^*Correspondence e-mail: 329408172@qq.com

Edited by H. Stoeckli-Evans, University of Neuchâtel, Switzerland (Received 24 September 2016; accepted 12 October 2016; online 28 October 2016)

The title benzothiazole derivative molecule, C₂₄H₂₃N₃S, is almost planar with the central benzene ring being inclined to the benzothiazole ring and the diethylaniline ring by 4.05 (13) and 5.05 (13)°, respectively. The conformation about the N=C bond is E. In the crystal, molecules are linked by C—H⋯π interactions, forming layers parallel to the ab plane.

Keywords: crystal structure; benzothiazole; Schiff base; C—H⋯π interactions.

CCDC reference: 1509540

Structure description

Benzothiazole derivatives are considered to be important because of their wide range of biological activities (Ali & Siddiqui, 2013 ). At the same time, their high electron affinity and good planarity make them appropriate building blocks for the construction of optical materials (Wang et al., 2010 ). Herein, we report on the synthesis and crystal structure of the title compound, a new benzothiazole derivative.

The molecular structure is illustrated in Fig. 1. The molecule is almost planar with the central benzene ring (C8–C13) being inclined to the benzothiazole ring (C15–C20; r.m.s. deviation = 0.021 Å) and the diethylaniline ring (C15–C20) by 4.05 (13) and 5.05 (13)°, respectively. The conformation about the N2=C14 bond is E.

Figure 1
The molecular structure of the title compound, showing the atom labelling. Displacement ellipsoids drawn at the 50% probability level.

In the crystal, molecules are linked by C—H⋯π interactions forming layers parallel to the ab plane (Table 1 and Fig. 2).

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C8–C13 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C12—H12⋯Cgⁱ	0.93	2.88	3.577 (5)	133
C17—H17⋯Cgⁱⁱ	0.93	2.93	3.646 (4)	135
Symmetry codes: (i) $[-x+2, y-{\script{1\over 2}}, -z+2]$ ; (ii) $[-x+1, y+{\script{1\over 2}}, -z+2]$ .

Figure 2
A view along the c axis of the crystal packing of the title compound. The C—H⋯π interactions are represented by dashed lines (see Table 1

), and only the H atoms (H12 and H17; grey balls) involved in these interactions have been included.

Synthesis and crystallization

4-(Diethylamino)salicylaldehyde (0.52 g, 2.7 mmol) was dissolved in 20 ml ethanol and added drop wise to a 20 ml ethanol solution of 4-(benzothiazol-2-yl)aniline (0.61 g, 2.7 mmol) with stirring. The mixture was stirred at room temperature, and then filtered. The filtrate was allow to evaporate slowly at room temperature and after one week, yellow block-like crystals were obtained (yield 62.0%).

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2.

Table 2
Experimental details

Crystal data
Chemical formula	C₂₄H₂₃N₃S
M_r	385.51
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	298
a, b, c (Å)	8.895 (5), 7.648 (5), 15.091 (5)
β (°)	98.566 (5)
V (Å³)	1015.2 (9)
Z	2
Radiation type	Mo Kα
μ (mm⁻¹)	0.17
Crystal size (mm)	0.30 × 0.20 × 0.20

Data collection
Diffractometer	Bruker SMART CCD area detector
Absorption correction	Multi-scan (SADABS; Bruker, 2004 )
T_min, T_max	0.950, 0.966
No. of measured, independent and observed [I > 2σ(I)] reflections	7218, 3278, 2690
R_int	0.024
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.122, 1.04
No. of reflections	3278
No. of parameters	256
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.23, −0.18
Absolute structure	Flack (1983 ), 1363 Friedel pairs
Absolute structure parameter	0.27 (10)
Computer programs: SMART and SAINT (Bruker, 2004), SHELXS97, SHELXL97 and SHELXTL (Sheldrick, 2008 ), Mercury (Macrae et al., 2008 ) and PLATON (Spek, 2009 ).

Structural data

CCDC reference: 1509540

Crystal structure: contains datablocks I, Global. DOI: https://doi.org/10.1107/S2414314616016217/su4082sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314616016217/su4082Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2414314616016217/su4082Isup3.cml

checkCIF report

Computing details top

Data collection: SMART (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

(E)-4-({[4-(Benzo[d]thiazol-2-yl)phenyl]imino}methyl)-N,N-diethylaniline top

Crystal data top

C₂₄H₂₃N₃S	F(000) = 408
M_r = 385.51	D_x = 1.261 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71069 Å
Hall symbol: P 2yb	Cell parameters from 2407 reflections
a = 8.895 (5) Å	θ = 2.5–23.5°
b = 7.648 (5) Å	µ = 0.17 mm⁻¹
c = 15.091 (5) Å	T = 298 K
β = 98.566 (5)°	Block, yellow
V = 1015.2 (9) Å³	0.30 × 0.20 × 0.20 mm
Z = 2

Data collection top

Bruker SMART CCD area detector diffractometer	3278 independent reflections
Radiation source: fine-focus sealed tube	2690 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.024
phi scans	θ_max = 25.0°, θ_min = 1.4°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −10→10
T_min = 0.950, T_max = 0.966	k = −8→9
7218 measured reflections	l = 0→17

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)] = 0.044	H-atom parameters constrained
wR(F²) = 0.122	w = 1/[σ²(F_o²) + (0.0719P)² + 0.0425P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max = 0.001
3278 reflections	Δρ_max = 0.23 e Å⁻³
256 parameters	Δρ_min = −0.18 e Å⁻³
1 restraint	Absolute structure: Flack (1983), 1363 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.27 (10)

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
S1	1.41511 (8)	0.16492 (14)	1.18673 (5)	0.0654 (3)
N1	1.2597 (3)	0.3273 (4)	1.29530 (16)	0.0583 (6)
N2	0.7097 (3)	0.2212 (3)	0.96102 (15)	0.0578 (7)
N3	0.0747 (3)	0.2513 (4)	0.69361 (15)	0.0600 (6)
C1	1.4589 (4)	0.3630 (6)	1.4264 (2)	0.0781 (11)
H1	1.3944	0.4240	1.4586	0.094*
C2	1.6035 (5)	0.3290 (7)	1.4630 (2)	0.0928 (13)
H2	1.6383	0.3681	1.5207	0.111*
C3	1.7014 (4)	0.2380 (6)	1.4172 (3)	0.0945 (14)
H3	1.7999	0.2151	1.4451	0.113*
C4	1.6555 (3)	0.1801 (6)	1.3303 (2)	0.0773 (10)
H4	1.7214	0.1199	1.2988	0.093*
C5	1.5068 (3)	0.2160 (4)	1.2925 (2)	0.0602 (8)
C6	1.4073 (3)	0.3051 (4)	1.33936 (19)	0.0588 (8)
C7	1.2487 (3)	0.2597 (4)	1.21464 (17)	0.0483 (6)
C8	1.1075 (3)	0.2557 (4)	1.15066 (17)	0.0462 (6)
C9	0.9747 (3)	0.3337 (4)	1.17029 (18)	0.0536 (7)
H9	0.9753	0.3904	1.2249	0.064*
C10	0.8426 (3)	0.3278 (4)	1.10960 (18)	0.0560 (7)
H10	0.7556	0.3824	1.1233	0.067*
C11	0.8375 (3)	0.2414 (4)	1.02829 (17)	0.0490 (6)
C12	0.9689 (3)	0.1634 (5)	1.00924 (17)	0.0541 (7)
H12	0.9677	0.1055	0.9550	0.065*
C13	1.1012 (3)	0.1698 (5)	1.06886 (17)	0.0562 (7)
H13	1.1881	0.1159	1.0544	0.067*
C14	0.5823 (3)	0.2863 (4)	0.96753 (18)	0.0551 (7)
H14	0.5718	0.3493	1.0190	0.066*
C15	0.4502 (3)	0.2683 (4)	0.89868 (17)	0.0470 (6)
C16	0.3150 (3)	0.3497 (4)	0.90676 (19)	0.0567 (7)
H16	0.3071	0.4113	0.9590	0.068*
C17	0.1925 (3)	0.3434 (4)	0.84128 (18)	0.0530 (7)
H17	0.1032	0.3998	0.8500	0.064*
C18	0.1979 (3)	0.2539 (4)	0.76100 (17)	0.0482 (6)
C19	0.3333 (3)	0.1671 (5)	0.75167 (17)	0.0532 (6)
H19	0.3405	0.1053	0.6994	0.064*
C20	0.4569 (3)	0.1725 (5)	0.81967 (18)	0.0548 (7)
H20	0.5452	0.1120	0.8130	0.066*
C21	−0.0560 (3)	0.3699 (5)	0.6928 (2)	0.0655 (9)
H21A	−0.0899	0.4077	0.6318	0.079*
H21B	−0.0234	0.4729	0.7281	0.079*
C22	−0.1861 (4)	0.2892 (6)	0.7288 (2)	0.0884 (12)
H22A	−0.2191	0.1870	0.6944	0.133*
H22B	−0.2682	0.3716	0.7251	0.133*
H22C	−0.1550	0.2568	0.7903	0.133*
C23	0.0718 (3)	0.1430 (5)	0.61427 (18)	0.0647 (9)
H23A	−0.0327	0.1119	0.5921	0.078*
H23B	0.1269	0.0356	0.6309	0.078*
C24	0.1398 (4)	0.2295 (6)	0.5403 (2)	0.0914 (13)
H24A	0.0835	0.3337	0.5217	0.137*
H24B	0.1355	0.1508	0.4905	0.137*
H24C	0.2437	0.2595	0.5614	0.137*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0536 (4)	0.0666 (5)	0.0750 (5)	0.0054 (4)	0.0065 (3)	−0.0112 (5)
N1	0.0498 (14)	0.0609 (16)	0.0624 (14)	−0.0015 (12)	0.0022 (11)	0.0012 (12)
N2	0.0528 (14)	0.0632 (19)	0.0567 (14)	0.0001 (12)	0.0060 (10)	0.0011 (12)
N3	0.0488 (13)	0.0723 (17)	0.0558 (13)	0.0090 (13)	−0.0018 (10)	−0.0137 (13)
C1	0.074 (2)	0.099 (3)	0.0584 (19)	−0.017 (2)	−0.0003 (16)	−0.0030 (18)
C2	0.097 (3)	0.109 (3)	0.064 (2)	−0.024 (3)	−0.016 (2)	0.011 (2)
C3	0.062 (2)	0.095 (3)	0.114 (3)	−0.016 (2)	−0.027 (2)	0.038 (3)
C4	0.0561 (18)	0.071 (2)	0.103 (3)	0.000 (2)	0.0046 (17)	0.008 (2)
C5	0.0527 (16)	0.052 (2)	0.0737 (19)	−0.0072 (14)	0.0014 (14)	0.0095 (14)
C6	0.0565 (17)	0.060 (2)	0.0586 (16)	−0.0093 (15)	0.0049 (13)	0.0057 (15)
C7	0.0511 (15)	0.0399 (15)	0.0534 (15)	−0.0045 (13)	0.0058 (12)	−0.0006 (13)
C8	0.0434 (14)	0.0407 (15)	0.0537 (14)	−0.0021 (13)	0.0047 (11)	0.0032 (13)
C9	0.0520 (16)	0.0570 (18)	0.0510 (15)	0.0000 (14)	0.0046 (12)	−0.0054 (14)
C10	0.0467 (15)	0.062 (2)	0.0584 (16)	0.0064 (14)	0.0067 (13)	−0.0047 (15)
C11	0.0504 (15)	0.0471 (16)	0.0485 (14)	−0.0050 (13)	0.0035 (11)	0.0045 (13)
C12	0.0539 (15)	0.0604 (17)	0.0473 (13)	−0.0001 (17)	0.0048 (11)	−0.0094 (15)
C13	0.0511 (14)	0.0612 (17)	0.0563 (15)	0.0068 (17)	0.0082 (11)	−0.0067 (17)
C14	0.0623 (19)	0.0495 (19)	0.0526 (15)	−0.0010 (15)	0.0057 (13)	−0.0013 (14)
C15	0.0484 (15)	0.0424 (16)	0.0499 (14)	−0.0065 (13)	0.0060 (11)	0.0007 (13)
C16	0.0598 (18)	0.0551 (19)	0.0555 (16)	0.0039 (15)	0.0098 (13)	−0.0068 (14)
C17	0.0475 (15)	0.0539 (18)	0.0572 (16)	0.0046 (14)	0.0061 (13)	−0.0097 (15)
C18	0.0488 (15)	0.0451 (15)	0.0508 (15)	−0.0004 (13)	0.0074 (11)	0.0000 (14)
C19	0.0498 (14)	0.0565 (16)	0.0532 (14)	0.0034 (17)	0.0076 (11)	−0.0069 (16)
C20	0.0428 (13)	0.0542 (16)	0.0693 (17)	0.0049 (15)	0.0146 (12)	0.0076 (17)
C21	0.0592 (19)	0.069 (2)	0.0660 (19)	0.0069 (17)	0.0019 (15)	−0.0037 (16)
C22	0.072 (2)	0.100 (3)	0.097 (3)	−0.003 (2)	0.0224 (19)	−0.009 (2)
C23	0.0601 (17)	0.074 (2)	0.0579 (16)	0.0041 (18)	0.0008 (13)	−0.0168 (18)
C24	0.100 (3)	0.113 (4)	0.064 (2)	0.003 (3)	0.0193 (19)	−0.004 (2)

Geometric parameters (Å, º) top

S1—C5	1.725 (3)	C12—C13	1.372 (3)
S1—C7	1.755 (3)	C12—H12	0.9300
N1—C7	1.313 (4)	C13—H13	0.9300
N1—C6	1.390 (4)	C14—C15	1.454 (4)
N2—C14	1.255 (4)	C14—H14	0.9300
N2—C11	1.415 (3)	C15—C16	1.376 (4)
N3—C18	1.379 (3)	C15—C20	1.408 (4)
N3—C23	1.453 (4)	C16—C17	1.358 (4)
N3—C21	1.474 (4)	C16—H16	0.9300
C1—C2	1.348 (5)	C17—C18	1.398 (4)
C1—C6	1.397 (4)	C17—H17	0.9300
C1—H1	0.9300	C18—C19	1.401 (4)
C2—C3	1.377 (6)	C19—C20	1.388 (3)
C2—H2	0.9300	C19—H19	0.9300
C3—C4	1.387 (5)	C20—H20	0.9300
C3—H3	0.9300	C21—C22	1.483 (5)
C4—C5	1.388 (4)	C21—H21A	0.9700
C4—H4	0.9300	C21—H21B	0.9700
C5—C6	1.391 (4)	C22—H22A	0.9600
C7—C8	1.466 (4)	C22—H22B	0.9600
C8—C13	1.392 (4)	C22—H22C	0.9600
C8—C9	1.394 (4)	C23—C24	1.500 (5)
C9—C10	1.379 (4)	C23—H23A	0.9700
C9—H9	0.9300	C23—H23B	0.9700
C10—C11	1.388 (4)	C24—H24A	0.9600
C10—H10	0.9300	C24—H24B	0.9600
C11—C12	1.380 (4)	C24—H24C	0.9600

C5—S1—C7	89.09 (14)	N2—C14—C15	123.3 (3)
C7—N1—C6	109.3 (2)	N2—C14—H14	118.3
C14—N2—C11	122.6 (2)	C15—C14—H14	118.3
C18—N3—C23	122.0 (2)	C16—C15—C20	117.3 (2)
C18—N3—C21	122.4 (2)	C16—C15—C14	121.2 (3)
C23—N3—C21	115.3 (2)	C20—C15—C14	121.5 (2)
C2—C1—C6	118.9 (4)	C17—C16—C15	122.5 (3)
C2—C1—H1	120.5	C17—C16—H16	118.8
C6—C1—H1	120.5	C15—C16—H16	118.8
C1—C2—C3	121.9 (4)	C16—C17—C18	121.3 (3)
C1—C2—H2	119.1	C16—C17—H17	119.3
C3—C2—H2	119.1	C18—C17—H17	119.3
C2—C3—C4	121.1 (3)	N3—C18—C17	121.3 (2)
C2—C3—H3	119.5	N3—C18—C19	121.3 (2)
C4—C3—H3	119.5	C17—C18—C19	117.4 (2)
C3—C4—C5	117.0 (4)	C20—C19—C18	120.7 (3)
C3—C4—H4	121.5	C20—C19—H19	119.7
C5—C4—H4	121.5	C18—C19—H19	119.7
C4—C5—C6	121.8 (3)	C19—C20—C15	120.8 (3)
C4—C5—S1	128.8 (3)	C19—C20—H20	119.6
C6—C5—S1	109.4 (2)	C15—C20—H20	119.6
N1—C6—C5	116.3 (3)	N3—C21—C22	113.5 (3)
N1—C6—C1	124.4 (3)	N3—C21—H21A	108.9
C5—C6—C1	119.2 (3)	C22—C21—H21A	108.9
N1—C7—C8	123.9 (2)	N3—C21—H21B	108.9
N1—C7—S1	115.9 (2)	C22—C21—H21B	108.9
C8—C7—S1	120.3 (2)	H21A—C21—H21B	107.7
C13—C8—C9	117.9 (2)	C21—C22—H22A	109.5
C13—C8—C7	120.7 (2)	C21—C22—H22B	109.5
C9—C8—C7	121.4 (2)	H22A—C22—H22B	109.5
C10—C9—C8	120.7 (3)	C21—C22—H22C	109.5
C10—C9—H9	119.7	H22A—C22—H22C	109.5
C8—C9—H9	119.7	H22B—C22—H22C	109.5
C9—C10—C11	121.0 (3)	N3—C23—C24	113.7 (3)
C9—C10—H10	119.5	N3—C23—H23A	108.8
C11—C10—H10	119.5	C24—C23—H23A	108.8
C12—C11—C10	118.2 (2)	N3—C23—H23B	108.8
C12—C11—N2	114.7 (2)	C24—C23—H23B	108.8
C10—C11—N2	127.1 (3)	H23A—C23—H23B	107.7
C13—C12—C11	121.2 (3)	C23—C24—H24A	109.5
C13—C12—H12	119.4	C23—C24—H24B	109.5
C11—C12—H12	119.4	H24A—C24—H24B	109.5
C12—C13—C8	121.0 (3)	C23—C24—H24C	109.5
C12—C13—H13	119.5	H24A—C24—H24C	109.5
C8—C13—H13	119.5	H24B—C24—H24C	109.5

C6—C1—C2—C3	−0.4 (6)	C14—N2—C11—C12	−179.0 (3)
C1—C2—C3—C4	1.2 (7)	C14—N2—C11—C10	1.9 (5)
C2—C3—C4—C5	−0.8 (6)	C10—C11—C12—C13	0.3 (5)
C3—C4—C5—C6	−0.4 (5)	N2—C11—C12—C13	−178.9 (3)
C3—C4—C5—S1	179.3 (3)	C11—C12—C13—C8	−0.1 (6)
C7—S1—C5—C4	178.3 (3)	C9—C8—C13—C12	0.5 (5)
C7—S1—C5—C6	−2.0 (2)	C7—C8—C13—C12	179.1 (3)
C7—N1—C6—C5	−1.7 (4)	C11—N2—C14—C15	179.4 (3)
C7—N1—C6—C1	179.5 (3)	N2—C14—C15—C16	−176.6 (3)
C4—C5—C6—N1	−177.7 (3)	N2—C14—C15—C20	1.0 (5)
S1—C5—C6—N1	2.6 (3)	C20—C15—C16—C17	−1.6 (5)
C4—C5—C6—C1	1.2 (5)	C14—C15—C16—C17	176.1 (3)
S1—C5—C6—C1	−178.6 (3)	C15—C16—C17—C18	−0.5 (5)
C2—C1—C6—N1	178.0 (4)	C23—N3—C18—C17	−172.8 (3)
C2—C1—C6—C5	−0.8 (5)	C21—N3—C18—C17	13.3 (5)
C6—N1—C7—C8	178.2 (3)	C23—N3—C18—C19	7.3 (5)
C6—N1—C7—S1	0.1 (3)	C21—N3—C18—C19	−166.7 (3)
C5—S1—C7—N1	1.2 (3)	C16—C17—C18—N3	−178.3 (3)
C5—S1—C7—C8	−177.0 (2)	C16—C17—C18—C19	1.6 (5)
N1—C7—C8—C13	−175.0 (3)	N3—C18—C19—C20	179.3 (3)
S1—C7—C8—C13	3.1 (4)	C17—C18—C19—C20	−0.7 (5)
N1—C7—C8—C9	3.5 (4)	C18—C19—C20—C15	−1.4 (5)
S1—C7—C8—C9	−178.4 (2)	C16—C15—C20—C19	2.5 (5)
C13—C8—C9—C10	−1.0 (4)	C14—C15—C20—C19	−175.2 (3)
C7—C8—C9—C10	−179.6 (3)	C18—N3—C21—C22	−97.4 (4)
C8—C9—C10—C11	1.2 (5)	C23—N3—C21—C22	88.3 (3)
C9—C10—C11—C12	−0.8 (5)	C18—N3—C23—C24	−87.5 (4)
C9—C10—C11—N2	178.3 (3)	C21—N3—C23—C24	86.9 (3)

Hydrogen-bond geometry (Å, º) top

Cg is the centroid of the C8–C13 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12···Cgⁱ	0.93	2.88	3.577 (5)	133
C17—H17···Cgⁱⁱ	0.93	2.93	3.646 (4)	135

Symmetry codes: (i) −x+2, y−1/2, −z+2; (ii) −x+1, y+1/2, −z+2.

Acknowledgements

This work was supported by the Graduate Students Innovative Program of Anhui University (grant Nos. J18515024, J18515019 and 201310357155).

References

Ali, R. & Siddiqui, N. (2013). J. Chem. Article ID 345198, 12 pp. https://dx.doi.org/10.1155/2013/345198 Google Scholar
Bruker (2004). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466–470. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
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https://doi.org/10.1107/S2414314616016217

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

(E)-4-({[4-(Benzo[d]thia­zol-2-yl)phen­yl]imino}­meth­yl)-N,N-di­ethyl­aniline

Structure description

Synthesis and crystallization

Refinement

Structural data

Acknowledgements

References

organic compounds

(E)-4-({[4-(Benzo[d]thiazol-2-yl)phenyl]imino}methyl)-N,N-diethylaniline