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A novel stilbene-based salicylhydrazone com­pound {systematic name: (E)-4,4′-(ethene-1,2-di­yl)bis­[(NE)-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.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229620008037/jx3056sup1.cif
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229620008037/jx3056Isup2.hkl
Contains datablock I

pdf

Portable Document Format (PDF) file https://doi.org/10.1107/S2053229620008037/jx3056sup3.pdf
1H NMR spectrum, mass spectra, photos of grown crystal, XRD, SEM images and TGA analysis

CCDC reference: 1977499

Computing details top

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 top
Crystal data top
C30H24N4O4·2C2H6OSF(000) = 696
Mr = 660.79Dx = 1.359 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 4.7581 (6) ÅCell parameters from 2855 reflections
b = 18.599 (2) Åθ = 2.2–24.8°
c = 18.266 (2) ŵ = 0.22 mm1
β = 92.409 (5)°T = 150 K
V = 1615.0 (3) Å3Long plate, yellow
Z = 21.00 × 0.80 × 0.01 mm
Data collection top
Bruker D8 VENTURE PHOTON II
diffractometer
1714 reflections with I > 2σ(I)
Radiation source: Ius 3.0Rint = 0.083
ω and phi scansθmax = 25.1°, θmin = 2.2°
Absorption correction: multi-scan
(SADABS; Bruker, 2012)
h = 55
Tmin = 0.589, Tmax = 0.745k = 2221
17483 measured reflectionsl = 2121
2816 independent reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.051H-atom parameters constrained
wR(F2) = 0.151 w = 1/[σ2(Fo2) + (0.0581P)2 + 1.0113P]
where P = (Fo2 + 2Fc2)/3
S = 1.07(Δ/σ)max < 0.001
2816 reflectionsΔρmax = 0.26 e Å3
208 parametersΔρmin = 0.34 e Å3
0 restraints
Special details top

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 (Å2) top
xyzUiso*/Ueq
O10.9364 (5)0.75111 (11)1.34452 (12)0.0461 (7)
H1A0.82780.77231.31650.055*
O20.4093 (5)0.78393 (11)1.19027 (12)0.0414 (6)
N10.6492 (5)0.85910 (13)1.29516 (13)0.0324 (7)
N20.4542 (5)0.88889 (13)1.25063 (13)0.0319 (7)
H2A0.40160.93401.25630.038*
C11.0492 (7)0.79944 (17)1.39020 (17)0.0355 (8)
C20.9720 (7)0.87243 (17)1.38986 (16)0.0319 (8)
C31.0979 (7)0.91854 (18)1.43910 (18)0.0393 (9)
H3A1.04810.96801.43960.047*
C41.2923 (8)0.8942 (2)1.48696 (18)0.0445 (9)
H4A1.37590.92641.52000.053*
C51.3645 (7)0.8220 (2)1.48630 (18)0.0450 (9)
H5A1.49780.80481.51940.054*
C61.2460 (7)0.77524 (19)1.43849 (18)0.0418 (9)
H6A1.29890.72601.43840.050*
C70.7644 (7)0.90022 (17)1.34077 (17)0.0331 (8)
H7A0.71450.94971.34280.040*
C80.3444 (7)0.84730 (17)1.19759 (16)0.0311 (8)
C90.1424 (7)0.88249 (15)1.14859 (16)0.0291 (7)
C100.0511 (7)0.84209 (17)1.09033 (17)0.0345 (8)
H10A0.11770.79431.08360.041*
C110.1340 (7)0.87015 (17)1.04216 (18)0.0368 (8)
H11A0.19270.84141.00260.044*
C120.2373 (7)0.94003 (17)1.05023 (17)0.0330 (8)
C130.1402 (7)0.98025 (17)1.10800 (18)0.0372 (8)
H13A0.20281.02851.11400.045*
C140.0444 (7)0.95246 (16)1.15692 (17)0.0335 (8)
H14A0.10450.98121.19630.040*
C150.4376 (7)0.96784 (16)0.99881 (18)0.0356 (8)
H15A0.48390.93700.95960.043*
S1S0.4159 (2)0.89954 (5)0.68655 (5)0.0424 (3)
O1S0.2730 (6)0.97004 (11)0.69869 (14)0.0601 (8)
C1S0.1520 (8)0.83818 (19)0.6599 (3)0.0644 (12)
H1SA0.23650.79100.65130.097*
H1SB0.05490.85500.61470.097*
H1SC0.01690.83420.69880.097*
C2S0.5060 (10)0.86450 (19)0.7747 (2)0.0629 (12)
H2SA0.60070.81810.76970.094*
H2SB0.33490.85800.80200.094*
H2SC0.63220.89810.80120.094*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0506 (17)0.0377 (13)0.0511 (15)0.0097 (12)0.0157 (12)0.0001 (11)
O20.0503 (16)0.0269 (12)0.0479 (14)0.0120 (11)0.0122 (12)0.0016 (10)
N10.0316 (17)0.0354 (15)0.0304 (15)0.0016 (13)0.0030 (12)0.0060 (12)
N20.0330 (16)0.0280 (14)0.0351 (15)0.0060 (12)0.0071 (12)0.0065 (12)
C10.035 (2)0.0375 (19)0.0337 (19)0.0007 (17)0.0003 (16)0.0044 (15)
C20.0253 (19)0.0382 (19)0.0320 (18)0.0021 (16)0.0005 (14)0.0049 (15)
C30.040 (2)0.040 (2)0.038 (2)0.0034 (17)0.0042 (17)0.0038 (16)
C40.044 (2)0.055 (2)0.034 (2)0.0067 (19)0.0075 (17)0.0056 (17)
C50.035 (2)0.063 (3)0.037 (2)0.0031 (19)0.0072 (16)0.0136 (18)
C60.041 (2)0.044 (2)0.041 (2)0.0081 (18)0.0032 (18)0.0110 (17)
C70.034 (2)0.0305 (17)0.0342 (18)0.0021 (16)0.0004 (15)0.0063 (15)
C80.031 (2)0.0306 (18)0.0311 (18)0.0022 (15)0.0008 (15)0.0062 (14)
C90.0272 (19)0.0265 (17)0.0332 (18)0.0003 (14)0.0023 (14)0.0066 (14)
C100.034 (2)0.0269 (17)0.043 (2)0.0015 (15)0.0061 (16)0.0042 (15)
C110.040 (2)0.0313 (18)0.040 (2)0.0010 (16)0.0088 (16)0.0009 (15)
C120.0273 (19)0.039 (2)0.0329 (18)0.0003 (16)0.0020 (15)0.0073 (15)
C130.039 (2)0.0323 (18)0.040 (2)0.0131 (16)0.0024 (16)0.0050 (15)
C140.038 (2)0.0293 (17)0.0336 (18)0.0030 (16)0.0036 (15)0.0016 (14)
C150.031 (2)0.0400 (19)0.0354 (19)0.0002 (16)0.0004 (15)0.0037 (16)
S1S0.0467 (6)0.0376 (5)0.0437 (6)0.0029 (4)0.0110 (4)0.0022 (4)
O1S0.095 (2)0.0223 (12)0.0630 (17)0.0027 (13)0.0075 (15)0.0006 (11)
C1S0.050 (3)0.036 (2)0.105 (3)0.005 (2)0.024 (2)0.010 (2)
C2S0.095 (4)0.040 (2)0.054 (3)0.008 (2)0.001 (2)0.0064 (18)
Geometric parameters (Å, º) top
O1—C11.353 (4)C9—C141.389 (4)
O1—H1A0.8400C10—C111.374 (4)
O2—C81.224 (4)C10—H10A0.9500
N1—C71.272 (4)C11—C121.395 (4)
N1—N21.376 (3)C11—H11A0.9500
N2—C81.361 (4)C12—C131.389 (4)
N2—H2A0.8800C12—C151.461 (4)
C1—C61.388 (4)C13—C141.379 (4)
C1—C21.407 (4)C13—H13A0.9500
C2—C31.396 (4)C14—H14A0.9500
C2—C71.456 (4)C15—C15i1.336 (6)
C3—C41.376 (5)C15—H15A0.9500
C3—H3A0.9500S1S—O1S1.498 (2)
C4—C51.385 (5)S1S—C1S1.750 (4)
C4—H4A0.9500S1S—C2S1.773 (4)
C5—C61.371 (5)C1S—H1SA0.9800
C5—H5A0.9500C1S—H1SB0.9800
C6—H6A0.9500C1S—H1SC0.9800
C7—H7A0.9500C2S—H2SA0.9800
C8—C91.492 (4)C2S—H2SB0.9800
C9—C101.387 (4)C2S—H2SC0.9800
C1—O1—H1A109.5C11—C10—H10A119.5
C7—N1—N2117.7 (3)C9—C10—H10A119.5
C8—N2—N1118.7 (2)C10—C11—C12121.3 (3)
C8—N2—H2A120.6C10—C11—H11A119.4
N1—N2—H2A120.6C12—C11—H11A119.4
O1—C1—C6118.2 (3)C13—C12—C11117.1 (3)
O1—C1—C2121.9 (3)C13—C12—C15123.0 (3)
C6—C1—C2119.9 (3)C11—C12—C15119.9 (3)
C3—C2—C1118.1 (3)C14—C13—C12122.1 (3)
C3—C2—C7120.0 (3)C14—C13—H13A118.9
C1—C2—C7121.9 (3)C12—C13—H13A118.9
C4—C3—C2121.7 (3)C13—C14—C9120.0 (3)
C4—C3—H3A119.2C13—C14—H14A120.0
C2—C3—H3A119.2C9—C14—H14A120.0
C3—C4—C5119.1 (3)C15i—C15—C12126.7 (4)
C3—C4—H4A120.4C15i—C15—H15A116.7
C5—C4—H4A120.4C12—C15—H15A116.7
C6—C5—C4120.8 (3)O1S—S1S—C1S106.69 (18)
C6—C5—H5A119.6O1S—S1S—C2S106.33 (16)
C4—C5—H5A119.6C1S—S1S—C2S99.0 (2)
C5—C6—C1120.4 (3)S1S—C1S—H1SA109.5
C5—C6—H6A119.8S1S—C1S—H1SB109.5
C1—C6—H6A119.8H1SA—C1S—H1SB109.5
N1—C7—C2120.8 (3)S1S—C1S—H1SC109.5
N1—C7—H7A119.6H1SA—C1S—H1SC109.5
C2—C7—H7A119.6H1SB—C1S—H1SC109.5
O2—C8—N2121.5 (3)S1S—C2S—H2SA109.5
O2—C8—C9121.5 (3)S1S—C2S—H2SB109.5
N2—C8—C9117.0 (3)H2SA—C2S—H2SB109.5
C10—C9—C14118.5 (3)S1S—C2S—H2SC109.5
C10—C9—C8116.9 (3)H2SA—C2S—H2SC109.5
C14—C9—C8124.6 (3)H2SB—C2S—H2SC109.5
C11—C10—C9121.0 (3)
Symmetry code: (i) x+1, y+2, z+2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1A···N10.841.872.611 (3)146
N2—H2A···O1Sii0.882.052.901 (3)163
C14—H14A···O1Sii0.952.303.234 (4)169
C7—H7A···O1Sii0.952.713.457 (4)136
C1S—H1SA···O2iii0.982.283.118 (4)143
C2S—H2SA···O2iii0.982.393.196 (4)139
C1S—H1SC···S1Siv0.983.113.735 (4)123
Symmetry codes: (ii) x, y+2, z+2; (iii) x+1, y+3/2, z1/2; (iv) x1, y, z.
 

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