A novel tetra­phenyl­ethyl­ene derivative: 4-methyl-N-[3-(1,2,2-tri­phenyl­ethen­yl)phen­yl]benzene­sulfonamide with aggregation-induced emission

The novel tetra­phenyl­ethyl­ene derivative 4-methyl-N-[3-(1,2,2-tri­phenyl­ethen­yl)phen­yl]benzene­sulfonamide (abbreviated as MTBF), C₃₃H₂₇NO₂S, was synthesized successfully and characterized by single-crystal X-ray diffraction, high-resolution mass spectroscopy and ¹H NMR spectroscopy. MTBF crystallizes in the centrosymmetric monoclinic space group P2₁/c. In the crystal structure, the MTBF mol­ecules are connected into a one-dimensional band and then a two-dimensional sheet by hydrogen bonds of the N—H...O and C—H...O types. The sheets are further linked to produce a three-dimensional network via C—H...π inter­actions. The mol­ecules aggregate via these inter­molecular forces, which restrain the intra­molecular motions (RIM) and decrease the energy loss in the aggregation state, so as to open the radiative channels, and thus MTBF exhibits excellent fluorescence by aggregation-induced emission (AIE) enhance­ment.

Computing details

Data collection: APEX2 (Bruker, 2016); cell refinement: SAINT (Bruker, 2016); data reduction: SAINT (Bruker, 2016); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015b); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

4-Methyl-N-[3-(1,2,2-triphenylethenyl)phenyl]benzenesulfonamide

Crystal data

C33H27NO2S	F(000) = 1056
Mr = 501.61	Dx = 1.244 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 16.4855 (4) Å	Cell parameters from 6788 reflections
b = 9.2994 (3) Å	θ = 2.5–26.4°
c = 19.0422 (5) Å	µ = 0.15 mm^−1
β = 113.403 (1)°	T = 150 K
V = 2679.11 (13) Å^3	Block, colourless
Z = 4	0.2 × 0.15 × 0.15 mm

Data collection

Bruker SMART APEX CCD diffractometer	4165 reflections with I > 2σ(I)
phi and ω scans	Rint = 0.062
Absorption correction: multi-scan (SADABS; Bruker, 2016)	θmax = 27.5°, θmin = 2.3°
Tmin = 0.705, Tmax = 0.746	h = −19→21
32198 measured reflections	k = −12→12
6150 independent reflections	l = −24→24

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.051	H-atom parameters constrained
wR(F^2) = 0.117	w = 1/[σ^2(Fo^2) + (0.0336P)^2 + 1.3428P] where P = (Fo^2 + 2Fc^2)/3
S = 1.07	(Δ/σ)max < 0.001
6150 reflections	Δρmax = 0.23 e Å^−3
335 parameters	Δρmin = −0.37 e Å^−3

Special details

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
S1	0.47887 (3)	0.34867 (6)	0.27558 (3)	0.03448 (15)
O1	0.41012 (9)	0.31640 (17)	0.20319 (8)	0.0432 (4)
O2	0.50141 (10)	0.49584 (15)	0.29755 (9)	0.0477 (4)
N1	0.56741 (10)	0.27036 (17)	0.27489 (9)	0.0296 (4)
H1	0.545653	0.188178	0.253622	0.035*
C1	0.3913 (2)	0.0719 (4)	0.52415 (17)	0.0873 (12)
H1A	0.361562	0.142383	0.544023	0.131*
H1B	0.445648	0.039013	0.565780	0.131*
H1C	0.352040	−0.010334	0.502755	0.131*
C2	0.41392 (16)	0.1408 (4)	0.46230 (15)	0.0603 (8)
C3	0.37437 (16)	0.0939 (3)	0.38763 (15)	0.0530 (7)
H3	0.333116	0.016937	0.375356	0.064*
C4	0.39375 (15)	0.1569 (3)	0.33014 (13)	0.0425 (5)
H4	0.366180	0.123221	0.278958	0.051*
C5	0.45352 (13)	0.2691 (2)	0.34793 (12)	0.0356 (5)
C6	0.49407 (16)	0.3185 (3)	0.42275 (14)	0.0522 (7)
H6	0.535185	0.395676	0.435239	0.063*
C7	0.47322 (18)	0.2529 (4)	0.47861 (15)	0.0666 (9)
H7	0.500673	0.286203	0.529872	0.080*
C8	0.64929 (12)	0.2718 (2)	0.34078 (10)	0.0248 (4)
C9	0.69110 (12)	0.4009 (2)	0.36972 (11)	0.0255 (4)
H9	0.664981	0.488813	0.346097	0.031*
C10	0.77116 (12)	0.40250 (19)	0.43321 (11)	0.0249 (4)
C11	0.80972 (12)	0.2727 (2)	0.46615 (11)	0.0278 (4)
H11	0.864296	0.272634	0.509588	0.033*
C12	0.76894 (13)	0.1443 (2)	0.43592 (11)	0.0313 (5)
H12	0.796231	0.056072	0.458079	0.038*
C13	0.68847 (13)	0.1429 (2)	0.37346 (11)	0.0298 (4)
H13	0.660350	0.054175	0.353173	0.036*
C14	0.81506 (12)	0.54454 (19)	0.46058 (11)	0.0247 (4)
C15	0.83795 (12)	0.5894 (2)	0.53304 (11)	0.0261 (4)
C16	0.81637 (13)	0.5019 (2)	0.58982 (11)	0.0293 (4)
C17	0.88397 (15)	0.4382 (2)	0.65132 (12)	0.0378 (5)
H17	0.943544	0.452104	0.657594	0.045*
C18	0.86612 (19)	0.3548 (2)	0.70361 (13)	0.0497 (6)
H18	0.913093	0.310003	0.744624	0.060*
C19	0.7804 (2)	0.3367 (3)	0.69616 (15)	0.0584 (8)
H19	0.767787	0.279312	0.731882	0.070*
C20	0.71267 (19)	0.4024 (3)	0.63656 (16)	0.0605 (8)
H20	0.653456	0.391603	0.631929	0.073*
C21	0.73031 (15)	0.4843 (3)	0.58313 (13)	0.0446 (6)
H21	0.683113	0.528171	0.541942	0.054*
C22	0.88375 (12)	0.7292 (2)	0.56142 (10)	0.0261 (4)
C23	0.96270 (13)	0.7638 (2)	0.55488 (11)	0.0337 (5)
H23	0.989553	0.696079	0.533463	0.040*
C24	1.00229 (14)	0.8962 (2)	0.57935 (12)	0.0408 (6)
H24	1.056548	0.918086	0.575289	0.049*
C25	0.96361 (15)	0.9961 (2)	0.60950 (12)	0.0414 (6)
H25	0.990333	1.087627	0.625135	0.050*
C26	0.88594 (15)	0.9630 (2)	0.61693 (12)	0.0379 (5)
H26	0.858986	1.032024	0.637569	0.046*
C27	0.84688 (14)	0.8292 (2)	0.59439 (11)	0.0313 (5)
H27	0.794589	0.805785	0.601563	0.038*
C28	0.82767 (12)	0.6302 (2)	0.39961 (10)	0.0247 (4)
C29	0.86605 (13)	0.5666 (2)	0.35404 (12)	0.0343 (5)
H29	0.886986	0.470414	0.363938	0.041*
C30	0.87398 (14)	0.6422 (3)	0.29442 (12)	0.0389 (5)
H30	0.900910	0.597820	0.264159	0.047*
C31	0.84314 (13)	0.7813 (2)	0.27862 (12)	0.0360 (5)
H31	0.848817	0.832836	0.237745	0.043*
C32	0.80412 (13)	0.8446 (2)	0.32252 (11)	0.0335 (5)
H32	0.782372	0.940221	0.311706	0.040*
C33	0.79630 (12)	0.7701 (2)	0.38233 (11)	0.0275 (4)
H33	0.769061	0.815278	0.412139	0.033*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0281 (3)	0.0301 (3)	0.0350 (3)	0.0023 (2)	0.0017 (2)	0.0069 (2)
O1	0.0308 (8)	0.0503 (10)	0.0343 (8)	−0.0017 (7)	−0.0019 (7)	0.0122 (7)
O2	0.0397 (9)	0.0270 (8)	0.0618 (11)	0.0045 (7)	0.0046 (8)	0.0061 (7)
N1	0.0267 (8)	0.0286 (9)	0.0266 (9)	−0.0042 (7)	0.0033 (7)	−0.0005 (7)
C1	0.0604 (18)	0.157 (3)	0.0588 (19)	0.031 (2)	0.0384 (16)	0.042 (2)
C2	0.0369 (13)	0.104 (2)	0.0440 (15)	0.0212 (15)	0.0205 (12)	0.0193 (15)
C3	0.0417 (13)	0.0658 (17)	0.0569 (17)	0.0051 (12)	0.0252 (13)	0.0136 (14)
C4	0.0385 (12)	0.0495 (14)	0.0392 (13)	−0.0006 (11)	0.0150 (10)	0.0002 (11)
C5	0.0278 (10)	0.0402 (12)	0.0349 (12)	0.0098 (9)	0.0083 (9)	0.0036 (10)
C6	0.0382 (13)	0.0722 (18)	0.0411 (14)	0.0013 (12)	0.0103 (11)	−0.0085 (13)
C7	0.0452 (15)	0.118 (3)	0.0341 (14)	0.0095 (17)	0.0130 (12)	−0.0052 (16)
C8	0.0254 (9)	0.0264 (10)	0.0214 (10)	−0.0012 (8)	0.0079 (8)	0.0017 (8)
C9	0.0270 (9)	0.0218 (9)	0.0258 (10)	0.0020 (8)	0.0085 (8)	0.0036 (8)
C10	0.0280 (9)	0.0236 (9)	0.0239 (10)	0.0002 (8)	0.0109 (8)	−0.0011 (8)
C11	0.0271 (10)	0.0278 (10)	0.0228 (10)	0.0026 (8)	0.0038 (8)	−0.0006 (8)
C12	0.0358 (11)	0.0197 (9)	0.0327 (11)	0.0039 (8)	0.0075 (9)	0.0036 (8)
C13	0.0335 (10)	0.0225 (10)	0.0291 (11)	−0.0034 (8)	0.0079 (9)	−0.0026 (8)
C14	0.0247 (9)	0.0229 (9)	0.0257 (10)	0.0016 (7)	0.0089 (8)	0.0012 (8)
C15	0.0253 (9)	0.0262 (10)	0.0252 (10)	0.0012 (8)	0.0083 (8)	−0.0019 (8)
C16	0.0389 (11)	0.0271 (10)	0.0247 (10)	−0.0049 (9)	0.0157 (9)	−0.0073 (8)
C17	0.0489 (13)	0.0346 (12)	0.0274 (11)	0.0005 (10)	0.0124 (10)	0.0023 (9)
C18	0.0830 (19)	0.0347 (12)	0.0317 (13)	−0.0011 (13)	0.0230 (13)	0.0040 (10)
C19	0.103 (2)	0.0434 (15)	0.0421 (15)	−0.0244 (15)	0.0434 (16)	−0.0053 (12)
C20	0.0677 (18)	0.0703 (19)	0.0593 (18)	−0.0299 (15)	0.0419 (16)	−0.0115 (15)
C21	0.0413 (13)	0.0555 (15)	0.0394 (13)	−0.0112 (11)	0.0186 (11)	−0.0046 (11)
C22	0.0288 (10)	0.0266 (10)	0.0194 (9)	−0.0031 (8)	0.0059 (8)	0.0005 (8)
C23	0.0304 (10)	0.0387 (12)	0.0286 (11)	−0.0041 (9)	0.0080 (9)	−0.0012 (9)
C24	0.0322 (11)	0.0445 (13)	0.0374 (13)	−0.0146 (10)	0.0050 (10)	0.0005 (10)
C25	0.0470 (13)	0.0308 (11)	0.0317 (12)	−0.0129 (10)	0.0000 (10)	−0.0011 (9)
C26	0.0519 (14)	0.0277 (11)	0.0275 (11)	0.0022 (10)	0.0087 (10)	−0.0021 (9)
C27	0.0375 (11)	0.0283 (11)	0.0267 (11)	−0.0007 (9)	0.0114 (9)	0.0002 (8)
C28	0.0220 (9)	0.0261 (10)	0.0228 (10)	−0.0043 (7)	0.0056 (8)	−0.0017 (8)
C29	0.0383 (11)	0.0313 (11)	0.0336 (12)	0.0091 (9)	0.0144 (10)	0.0028 (9)
C30	0.0396 (12)	0.0525 (14)	0.0289 (11)	0.0019 (10)	0.0181 (10)	0.0011 (10)
C31	0.0354 (11)	0.0431 (13)	0.0255 (11)	−0.0092 (10)	0.0079 (9)	0.0069 (9)
C32	0.0380 (11)	0.0279 (11)	0.0306 (11)	−0.0042 (9)	0.0094 (9)	0.0029 (9)
C33	0.0305 (10)	0.0251 (10)	0.0252 (10)	−0.0021 (8)	0.0092 (8)	−0.0011 (8)

Geometric parameters (Å, º)

S1—O1	1.4260 (15)	C15—C22	1.493 (3)
S1—O2	1.4362 (15)	C16—C17	1.389 (3)
S1—N1	1.6360 (17)	C16—C21	1.383 (3)
S1—C5	1.754 (2)	C17—H17	0.9500
N1—H1	0.8726	C17—C18	1.383 (3)
N1—C8	1.432 (2)	C18—H18	0.9500
C1—H1A	0.9800	C18—C19	1.374 (4)
C1—H1B	0.9800	C19—H19	0.9500
C1—H1C	0.9800	C19—C20	1.379 (4)
C1—C2	1.512 (4)	C20—H20	0.9500
C2—C3	1.379 (4)	C20—C21	1.391 (3)
C2—C7	1.378 (4)	C21—H21	0.9500
C3—H3	0.9500	C22—C23	1.394 (3)
C3—C4	1.386 (3)	C22—C27	1.390 (3)
C4—H4	0.9500	C23—H23	0.9500
C4—C5	1.382 (3)	C23—C24	1.384 (3)
C5—C6	1.390 (3)	C24—H24	0.9500
C6—H6	0.9500	C24—C25	1.375 (3)
C6—C7	1.383 (4)	C25—H25	0.9500
C7—H7	0.9500	C25—C26	1.378 (3)
C8—C9	1.385 (3)	C26—H26	0.9500
C8—C13	1.386 (3)	C26—C27	1.389 (3)
C9—H9	0.9500	C27—H27	0.9500
C9—C10	1.392 (3)	C28—C29	1.392 (3)
C10—C11	1.392 (3)	C28—C33	1.391 (3)
C10—C14	1.497 (3)	C29—H29	0.9500
C11—H11	0.9500	C29—C30	1.385 (3)
C11—C12	1.380 (3)	C30—H30	0.9500
C12—H12	0.9500	C30—C31	1.379 (3)
C12—C13	1.386 (3)	C31—H31	0.9500
C13—H13	0.9500	C31—C32	1.374 (3)
C14—C15	1.344 (3)	C32—H32	0.9500
C14—C28	1.489 (3)	C32—C33	1.382 (3)
C15—C16	1.504 (3)	C33—H33	0.9500
O1—S1—O2	119.77 (9)	C22—C15—C16	116.16 (16)
O1—S1—N1	105.53 (9)	C17—C16—C15	119.83 (19)
O1—S1—C5	108.94 (10)	C21—C16—C15	121.65 (19)
O2—S1—N1	107.34 (9)	C21—C16—C17	118.5 (2)
O2—S1—C5	106.74 (11)	C16—C17—H17	119.4
N1—S1—C5	108.07 (9)	C18—C17—C16	121.2 (2)
S1—N1—H1	100.9	C18—C17—H17	119.4
C8—N1—S1	121.49 (13)	C17—C18—H18	120.0
C8—N1—H1	119.0	C19—C18—C17	119.9 (2)
H1A—C1—H1B	109.5	C19—C18—H18	120.0
H1A—C1—H1C	109.5	C18—C19—H19	120.2
H1B—C1—H1C	109.5	C18—C19—C20	119.6 (2)
C2—C1—H1A	109.5	C20—C19—H19	120.2
C2—C1—H1B	109.5	C19—C20—H20	119.7
C2—C1—H1C	109.5	C19—C20—C21	120.6 (3)
C3—C2—C1	120.5 (3)	C21—C20—H20	119.7
C7—C2—C1	121.2 (3)	C16—C21—C20	120.2 (2)
C7—C2—C3	118.3 (2)	C16—C21—H21	119.9
C2—C3—H3	119.4	C20—C21—H21	119.9
C2—C3—C4	121.2 (3)	C23—C22—C15	121.66 (18)
C4—C3—H3	119.4	C27—C22—C15	119.81 (17)
C3—C4—H4	120.3	C27—C22—C23	118.53 (18)
C5—C4—C3	119.4 (2)	C22—C23—H23	119.8
C5—C4—H4	120.3	C24—C23—C22	120.5 (2)
C4—C5—S1	119.68 (17)	C24—C23—H23	119.8
C4—C5—C6	120.5 (2)	C23—C24—H24	119.8
C6—C5—S1	119.86 (19)	C25—C24—C23	120.4 (2)
C5—C6—H6	120.7	C25—C24—H24	119.8
C7—C6—C5	118.5 (3)	C24—C25—H25	120.1
C7—C6—H6	120.7	C24—C25—C26	119.7 (2)
C2—C7—C6	122.1 (3)	C26—C25—H25	120.1
C2—C7—H7	118.9	C25—C26—H26	119.9
C6—C7—H7	118.9	C25—C26—C27	120.3 (2)
C9—C8—N1	120.24 (16)	C27—C26—H26	119.9
C9—C8—C13	120.09 (16)	C22—C27—H27	119.8
C13—C8—N1	119.61 (16)	C26—C27—C22	120.5 (2)
C8—C9—H9	119.8	C26—C27—H27	119.8
C8—C9—C10	120.36 (17)	C29—C28—C14	119.84 (17)
C10—C9—H9	119.8	C33—C28—C14	122.06 (17)
C9—C10—C11	119.21 (17)	C33—C28—C29	117.92 (18)
C9—C10—C14	118.20 (16)	C28—C29—H29	119.7
C11—C10—C14	122.49 (16)	C30—C29—C28	120.62 (19)
C10—C11—H11	119.9	C30—C29—H29	119.7
C12—C11—C10	120.21 (17)	C29—C30—H30	119.7
C12—C11—H11	119.9	C31—C30—C29	120.6 (2)
C11—C12—H12	119.7	C31—C30—H30	119.7
C11—C12—C13	120.52 (17)	C30—C31—H31	120.3
C13—C12—H12	119.7	C32—C31—C30	119.4 (2)
C8—C13—H13	120.2	C32—C31—H31	120.3
C12—C13—C8	119.57 (17)	C31—C32—H32	119.8
C12—C13—H13	120.2	C31—C32—C33	120.4 (2)
C15—C14—C10	122.07 (17)	C33—C32—H32	119.8
C15—C14—C28	124.43 (17)	C28—C33—H33	119.5
C28—C14—C10	113.48 (16)	C32—C33—C28	121.09 (19)
C14—C15—C16	121.32 (17)	C32—C33—H33	119.5
C14—C15—C22	122.50 (18)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2^i	0.87	2.04	2.909 (2)	178
C1—H1A···O1^ii	0.98	2.84	3.458 (4)	122
C13—H13···O1^i	0.95	2.53	3.479 (2)	178

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