Solvent-assisted planar structure of a stilbene-based salicylhydrazone com­pound: crystal structure, solvent- and aggregation-induced emission, and switchable luminescence colouration

A novel stilbene-based salicylhydrazone com­pound {systematic name: (E)-4,4′-(ethene-1,2-di­yl)bis­[(N′E)-N′-(2-hy­droxy­benzyl­idene)benzohydrazide] di­methyl sulfoxide disolvate, C₃₀H₂₄N₄O₄·2C₂H₆OS or L·2DMSO} was synthesized and characterized by single-crystal X-ray diffraction, powder X-ray diffraction and luminescence spectroscopy. The title com­pound crystallizes in the monoclinic space group P2₁/c, with half a symmetry-independent L mol­ecule and one dimethyl sulfoxide (DMSO) solvent mol­ecule in the asymmetric unit. The L molecule adopts an almost planar structure, with a small dihedral angle between the planes of the stilbene and salicylhydrazone groups. There are multiple π–π stacking inter­actions between adjacent L mol­ecules. The DMSO solvent mol­e­cules act as proton donors and acceptors, forming hydrogen bonds of various strengths with the L mol­ecules. In addition, the geometry optimization of a single mol­ecule of L and its luminescence properties either in solution, as a solvated solid or as a desolvated solid were studied. The com­pound shows an aggregation-induced emission (AIE) effect and exhibits switchable luminescence colouration in the solid state by the simple removal or re-addition of the DMSO solvent.

Computing details

Data collection: SAINT (Bruker, 2012); cell refinement: APEX2 (Bruker, 2012); data reduction: SAINT (Bruker, 2012); program(s) used to solve structure: olex2.solve (Bourhis et al., 2015); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

(E)-4,4'-(Ethene-1,2-diyl)bis[(N'E)-N'-(2-hydroxybenzylidene)benzohydrazide] dimethyl sulfoxide disolvate

Crystal data

C30H24N4O4·2C2H6OS	F(000) = 696
Mr = 660.79	Dx = 1.359 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 4.7581 (6) Å	Cell parameters from 2855 reflections
b = 18.599 (2) Å	θ = 2.2–24.8°
c = 18.266 (2) Å	µ = 0.22 mm^−1
β = 92.409 (5)°	T = 150 K
V = 1615.0 (3) Å^3	Long plate, yellow
Z = 2	1.00 × 0.80 × 0.01 mm

Data collection

Bruker D8 VENTURE PHOTON II diffractometer	1714 reflections with I > 2σ(I)
Radiation source: Ius 3.0	Rint = 0.083
ω and phi scans	θmax = 25.1°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2012)	h = −5→5
Tmin = 0.589, Tmax = 0.745	k = −22→21
17483 measured reflections	l = −21→21
2816 independent reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.051	H-atom parameters constrained
wR(F^2) = 0.151	w = 1/[σ^2(Fo^2) + (0.0581P)^2 + 1.0113P] where P = (Fo^2 + 2Fc^2)/3
S = 1.07	(Δ/σ)max < 0.001
2816 reflections	Δρmax = 0.26 e Å^−3
208 parameters	Δρmin = −0.34 e Å^−3
0 restraints

Special details

Experimental. SADABS (Bruker, 2012) was used for absorption correction. wR2(int) was 0.1447 before and 0.0772 after correction. The Ratio of minimum to maximum transmission is 0.7904. The λ/2 correction factor is Not present.

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O1	−0.9364 (5)	0.75111 (11)	1.34452 (12)	0.0461 (7)
H1A	−0.8278	0.7723	1.3165	0.055*
O2	−0.4093 (5)	0.78393 (11)	1.19027 (12)	0.0414 (6)
N1	−0.6492 (5)	0.85910 (13)	1.29516 (13)	0.0324 (7)
N2	−0.4542 (5)	0.88889 (13)	1.25063 (13)	0.0319 (7)
H2A	−0.4016	0.9340	1.2563	0.038*
C1	−1.0492 (7)	0.79944 (17)	1.39020 (17)	0.0355 (8)
C2	−0.9720 (7)	0.87243 (17)	1.38986 (16)	0.0319 (8)
C3	−1.0979 (7)	0.91854 (18)	1.43910 (18)	0.0393 (9)
H3A	−1.0481	0.9680	1.4396	0.047*
C4	−1.2923 (8)	0.8942 (2)	1.48696 (18)	0.0445 (9)
H4A	−1.3759	0.9264	1.5200	0.053*
C5	−1.3645 (7)	0.8220 (2)	1.48630 (18)	0.0450 (9)
H5A	−1.4978	0.8048	1.5194	0.054*
C6	−1.2460 (7)	0.77524 (19)	1.43849 (18)	0.0418 (9)
H6A	−1.2989	0.7260	1.4384	0.050*
C7	−0.7644 (7)	0.90022 (17)	1.34077 (17)	0.0331 (8)
H7A	−0.7145	0.9497	1.3428	0.040*
C8	−0.3444 (7)	0.84730 (17)	1.19759 (16)	0.0311 (8)
C9	−0.1424 (7)	0.88249 (15)	1.14859 (16)	0.0291 (7)
C10	−0.0511 (7)	0.84209 (17)	1.09033 (17)	0.0345 (8)
H10A	−0.1177	0.7943	1.0836	0.041*
C11	0.1340 (7)	0.87015 (17)	1.04216 (18)	0.0368 (8)
H11A	0.1927	0.8414	1.0026	0.044*
C12	0.2373 (7)	0.94003 (17)	1.05023 (17)	0.0330 (8)
C13	0.1402 (7)	0.98025 (17)	1.10800 (18)	0.0372 (8)
H13A	0.2028	1.0285	1.1140	0.045*
C14	−0.0444 (7)	0.95246 (16)	1.15692 (17)	0.0335 (8)
H14A	−0.1045	0.9812	1.1963	0.040*
C15	0.4376 (7)	0.96784 (16)	0.99881 (18)	0.0356 (8)
H15A	0.4839	0.9370	0.9596	0.043*
S1S	0.4159 (2)	0.89954 (5)	0.68655 (5)	0.0424 (3)
O1S	0.2730 (6)	0.97004 (11)	0.69869 (14)	0.0601 (8)
C1S	0.1520 (8)	0.83818 (19)	0.6599 (3)	0.0644 (12)
H1SA	0.2365	0.7910	0.6513	0.097*
H1SB	0.0549	0.8550	0.6147	0.097*
H1SC	0.0169	0.8342	0.6988	0.097*
C2S	0.5060 (10)	0.86450 (19)	0.7747 (2)	0.0629 (12)
H2SA	0.6007	0.8181	0.7697	0.094*
H2SB	0.3349	0.8580	0.8020	0.094*
H2SC	0.6322	0.8981	0.8012	0.094*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0506 (17)	0.0377 (13)	0.0511 (15)	−0.0097 (12)	0.0157 (12)	0.0001 (11)
O2	0.0503 (16)	0.0269 (12)	0.0479 (14)	−0.0120 (11)	0.0122 (12)	0.0016 (10)
N1	0.0316 (17)	0.0354 (15)	0.0304 (15)	−0.0016 (13)	0.0030 (12)	0.0060 (12)
N2	0.0330 (16)	0.0280 (14)	0.0351 (15)	−0.0060 (12)	0.0071 (12)	0.0065 (12)
C1	0.035 (2)	0.0375 (19)	0.0337 (19)	0.0007 (17)	−0.0003 (16)	0.0044 (15)
C2	0.0253 (19)	0.0382 (19)	0.0320 (18)	−0.0021 (16)	0.0005 (14)	0.0049 (15)
C3	0.040 (2)	0.040 (2)	0.038 (2)	0.0034 (17)	0.0042 (17)	0.0038 (16)
C4	0.044 (2)	0.055 (2)	0.034 (2)	0.0067 (19)	0.0075 (17)	0.0056 (17)
C5	0.035 (2)	0.063 (3)	0.037 (2)	−0.0031 (19)	0.0072 (16)	0.0136 (18)
C6	0.041 (2)	0.044 (2)	0.041 (2)	−0.0081 (18)	0.0032 (18)	0.0110 (17)
C7	0.034 (2)	0.0305 (17)	0.0342 (18)	−0.0021 (16)	−0.0004 (15)	0.0063 (15)
C8	0.031 (2)	0.0306 (18)	0.0311 (18)	−0.0022 (15)	−0.0008 (15)	0.0062 (14)
C9	0.0272 (19)	0.0265 (17)	0.0332 (18)	0.0003 (14)	−0.0023 (14)	0.0066 (14)
C10	0.034 (2)	0.0269 (17)	0.043 (2)	−0.0015 (15)	0.0061 (16)	0.0042 (15)
C11	0.040 (2)	0.0313 (18)	0.040 (2)	0.0010 (16)	0.0088 (16)	0.0009 (15)
C12	0.0273 (19)	0.039 (2)	0.0329 (18)	−0.0003 (16)	0.0020 (15)	0.0073 (15)
C13	0.039 (2)	0.0323 (18)	0.040 (2)	−0.0131 (16)	0.0024 (16)	0.0050 (15)
C14	0.038 (2)	0.0293 (17)	0.0336 (18)	−0.0030 (16)	0.0036 (15)	−0.0016 (14)
C15	0.031 (2)	0.0400 (19)	0.0354 (19)	−0.0002 (16)	0.0004 (15)	0.0037 (16)
S1S	0.0467 (6)	0.0376 (5)	0.0437 (6)	−0.0029 (4)	0.0110 (4)	−0.0022 (4)
O1S	0.095 (2)	0.0223 (12)	0.0630 (17)	0.0027 (13)	0.0075 (15)	−0.0006 (11)
C1S	0.050 (3)	0.036 (2)	0.105 (3)	0.005 (2)	−0.024 (2)	−0.010 (2)
C2S	0.095 (4)	0.040 (2)	0.054 (3)	0.008 (2)	−0.001 (2)	−0.0064 (18)

Geometric parameters (Å, º)

O1—C1	1.353 (4)	C9—C14	1.389 (4)
O1—H1A	0.8400	C10—C11	1.374 (4)
O2—C8	1.224 (4)	C10—H10A	0.9500
N1—C7	1.272 (4)	C11—C12	1.395 (4)
N1—N2	1.376 (3)	C11—H11A	0.9500
N2—C8	1.361 (4)	C12—C13	1.389 (4)
N2—H2A	0.8800	C12—C15	1.461 (4)
C1—C6	1.388 (4)	C13—C14	1.379 (4)
C1—C2	1.407 (4)	C13—H13A	0.9500
C2—C3	1.396 (4)	C14—H14A	0.9500
C2—C7	1.456 (4)	C15—C15^i	1.336 (6)
C3—C4	1.376 (5)	C15—H15A	0.9500
C3—H3A	0.9500	S1S—O1S	1.498 (2)
C4—C5	1.385 (5)	S1S—C1S	1.750 (4)
C4—H4A	0.9500	S1S—C2S	1.773 (4)
C5—C6	1.371 (5)	C1S—H1SA	0.9800
C5—H5A	0.9500	C1S—H1SB	0.9800
C6—H6A	0.9500	C1S—H1SC	0.9800
C7—H7A	0.9500	C2S—H2SA	0.9800
C8—C9	1.492 (4)	C2S—H2SB	0.9800
C9—C10	1.387 (4)	C2S—H2SC	0.9800
C1—O1—H1A	109.5	C11—C10—H10A	119.5
C7—N1—N2	117.7 (3)	C9—C10—H10A	119.5
C8—N2—N1	118.7 (2)	C10—C11—C12	121.3 (3)
C8—N2—H2A	120.6	C10—C11—H11A	119.4
N1—N2—H2A	120.6	C12—C11—H11A	119.4
O1—C1—C6	118.2 (3)	C13—C12—C11	117.1 (3)
O1—C1—C2	121.9 (3)	C13—C12—C15	123.0 (3)
C6—C1—C2	119.9 (3)	C11—C12—C15	119.9 (3)
C3—C2—C1	118.1 (3)	C14—C13—C12	122.1 (3)
C3—C2—C7	120.0 (3)	C14—C13—H13A	118.9
C1—C2—C7	121.9 (3)	C12—C13—H13A	118.9
C4—C3—C2	121.7 (3)	C13—C14—C9	120.0 (3)
C4—C3—H3A	119.2	C13—C14—H14A	120.0
C2—C3—H3A	119.2	C9—C14—H14A	120.0
C3—C4—C5	119.1 (3)	C15^i—C15—C12	126.7 (4)
C3—C4—H4A	120.4	C15^i—C15—H15A	116.7
C5—C4—H4A	120.4	C12—C15—H15A	116.7
C6—C5—C4	120.8 (3)	O1S—S1S—C1S	106.69 (18)
C6—C5—H5A	119.6	O1S—S1S—C2S	106.33 (16)
C4—C5—H5A	119.6	C1S—S1S—C2S	99.0 (2)
C5—C6—C1	120.4 (3)	S1S—C1S—H1SA	109.5
C5—C6—H6A	119.8	S1S—C1S—H1SB	109.5
C1—C6—H6A	119.8	H1SA—C1S—H1SB	109.5
N1—C7—C2	120.8 (3)	S1S—C1S—H1SC	109.5
N1—C7—H7A	119.6	H1SA—C1S—H1SC	109.5
C2—C7—H7A	119.6	H1SB—C1S—H1SC	109.5
O2—C8—N2	121.5 (3)	S1S—C2S—H2SA	109.5
O2—C8—C9	121.5 (3)	S1S—C2S—H2SB	109.5
N2—C8—C9	117.0 (3)	H2SA—C2S—H2SB	109.5
C10—C9—C14	118.5 (3)	S1S—C2S—H2SC	109.5
C10—C9—C8	116.9 (3)	H2SA—C2S—H2SC	109.5
C14—C9—C8	124.6 (3)	H2SB—C2S—H2SC	109.5
C11—C10—C9	121.0 (3)

Symmetry code: (i) −x+1, −y+2, −z+2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···N1	0.84	1.87	2.611 (3)	146
N2—H2A···O1S^ii	0.88	2.05	2.901 (3)	163
C14—H14A···O1S^ii	0.95	2.30	3.234 (4)	169
C7—H7A···O1S^ii	0.95	2.71	3.457 (4)	136
C1S—H1SA···O2^iii	0.98	2.28	3.118 (4)	143
C2S—H2SA···O2^iii	0.98	2.39	3.196 (4)	139
C1S—H1SC···S1S^iv	0.98	3.11	3.735 (4)	123

Symmetry codes: (ii) −x, −y+2, −z+2; (iii) x+1, −y+3/2, z−1/2; (iv) x−1, y, z.