4-(Diphenyl-amino)-benzaldehyde 4-phenyl-thio-semicarbazone.

The title mol-ecule, C(26)H(22)N(4)S, is composed of three main parts, viz. a triphenyl-amine group is connected to a phenyl ring by a thio-semicarbazone moiety. The C= N double bond has an E conformation. The crystal packing is dominated by strong hydrogen bonds through the thio-semicarbazone moiety, with pairs of N-H⋯S hydrogen bonds linking the mol-ecules to form inversion dimers with an R(2) (2)(8) ring motif. An intra-molecular N-H⋯N hydrogen bond is also present, generating an S(5) ring motif. Although the structure contains four phenyl rings, π-π stacking inter-actions are not formed between them, probably due to the conformation adopted by the triphenyl-amine group. However, a weak π-π stacking inter-action is observed between the phenyl ring and the delocalized thio-semicarbazone moiety.

Related literature

For related compounds and their biological activity, see: Gupta et al. (2007 ▶); Lee et al. (2010 ▶); Odenike et al. (2008 ▶). For hydrogen-bond motifs, see Bernstein et al. (1995 ▶). For a description of the Cambridge Structural Database, see: Allen (2002 ▶).

Experimental

Crystal data

C26H22N4S

M = 422.55

Monoclinic,

a = 13.6069 (3) Å

b = 15.2763 (3) Å

c = 11.2778 (2) Å

β = 104.094 (2)°

V = 2273.67 (8) Å3

Z = 4

Cu Kα radiation

μ = 1.41 mm−1

T = 285 K

0.17 × 0.09 × 0.05 mm

Data collection

Oxford Xcalibur diffractometer with Onyx Nova detector

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010 ▶) T min = 0.726, T max = 1.000

26370 measured reflections

4623 independent reflections

3535 reflections with I > 2σ(I)

R int = 0.067

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.149

S = 1.07

4623 reflections

369 parameters

All H-atom parameters refined

Δρmax = 0.20 e Å−3

Δρmin = −0.29 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2010 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2010 ▶); data reduction: CrysAlis RED; program(s) used to solve structure: SIR08 (Burla et al., 2007 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶), PLATON (Spek, 2009 ▶), PARST95 (Nardelli, 1995 ▶) and publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S160053681203053X/lr2069sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681203053X/lr2069Isup2.hkl

Supplementary material file. DOI: 10.1107/S160053681203053X/lr2069Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C26H22N4S	F(000) = 888
Mr = 422.55	Dx = 1.234 Mg m−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54180 Å
Hall symbol: -P 2ybc	Cell parameters from 8693 reflections
a = 13.6069 (3) Å	θ = 2.9–75.3°
b = 15.2763 (3) Å	µ = 1.41 mm−1
c = 11.2778 (2) Å	T = 285 K
β = 104.094 (2)°	Plate, dark yellow
V = 2273.67 (8) Å3	0.17 × 0.09 × 0.05 mm
Z = 4

Oxford Xcalibur diffractometer with Onyx Nova detector	4623 independent reflections
Radiation source: Nova (Cu) X-ray Source	3535 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.067
Detector resolution: 8.2640 pixels mm-1	θmax = 75.5°, θmin = 3.4°
ω scans	h = −16→16
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	k = −17→18
Tmin = 0.726, Tmax = 1.000	l = −11→14
26370 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.049	All H-atom parameters refined
wR(F2) = 0.149	w = 1/[σ2(Fo2) + (0.0766P)2 + 0.2813P] where P = (Fo2 + 2Fc2)/3
S = 1.07	(Δ/σ)max < 0.001
4623 reflections	Δρmax = 0.20 e Å−3
369 parameters	Δρmin = −0.29 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: 0.0012 (3)

Experimental. Absorption correction: CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.36 (release 02-08-2010 CrysAlis171 .NET) (compiled Aug 2 2010,13:00:58) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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.

	x	y	z	Uiso*/Ueq
S1	0.94600 (4)	0.03619 (4)	0.15627 (5)	0.0689 (2)
N2	1.16947 (11)	0.16240 (10)	0.07520 (14)	0.0504 (4)
N3	1.08689 (11)	0.10941 (11)	0.06823 (15)	0.0522 (4)
N4	1.08031 (14)	0.15773 (11)	0.25732 (15)	0.0591 (4)
N1	1.56053 (12)	0.35772 (12)	−0.02307 (15)	0.0597 (4)
C8	1.21068 (14)	0.15830 (13)	−0.01584 (17)	0.0520 (4)
C14	1.33120 (14)	0.27924 (13)	0.06329 (17)	0.0527 (4)
C9	1.29891 (13)	0.21151 (12)	−0.01924 (16)	0.0490 (4)
C7	1.04293 (14)	0.10515 (12)	0.16271 (16)	0.0510 (4)
C12	1.47208 (13)	0.30889 (12)	−0.02447 (17)	0.0508 (4)
C13	1.41611 (15)	0.32736 (13)	0.06068 (18)	0.0534 (4)
C15	1.58656 (15)	0.38294 (13)	−0.13237 (19)	0.0554 (5)
C11	1.43998 (16)	0.24198 (14)	−0.10803 (19)	0.0611 (5)
C10	1.35392 (16)	0.19418 (14)	−0.10567 (18)	0.0585 (5)
C6	1.04960 (16)	0.15504 (13)	0.37043 (18)	0.0573 (5)
C21	1.62500 (14)	0.38028 (13)	0.09250 (18)	0.0559 (5)
C20	1.68751 (18)	0.39145 (16)	−0.1348 (3)	0.0717 (6)
C5	0.97506 (19)	0.20986 (19)	0.3890 (2)	0.0749 (6)
C16	1.5132 (2)	0.40044 (16)	−0.2379 (2)	0.0706 (6)
C22	1.66006 (18)	0.46481 (15)	0.1163 (2)	0.0680 (6)
C3	0.9924 (3)	0.1471 (2)	0.5872 (3)	0.0880 (8)
C1	1.0965 (2)	0.09751 (18)	0.4592 (2)	0.0832 (7)
C19	1.7123 (3)	0.4176 (2)	−0.2411 (4)	0.0966 (10)
C23	1.7227 (2)	0.4862 (2)	0.2285 (3)	0.0841 (7)
C17	1.5399 (3)	0.4254 (2)	−0.3436 (3)	0.0895 (8)
C18	1.6401 (3)	0.4340 (2)	−0.3447 (4)	0.1005 (10)
C26	1.6521 (2)	0.31817 (18)	0.1832 (2)	0.0818 (7)
C2	1.0684 (3)	0.0947 (2)	0.5689 (3)	0.1006 (10)
C4	0.9469 (2)	0.2052 (2)	0.5001 (3)	0.0877 (8)
C24	1.7493 (2)	0.4241 (2)	0.3180 (3)	0.0984 (9)
C25	1.7131 (3)	0.3415 (2)	0.2959 (3)	0.1070 (11)
H8	1.1832 (15)	0.1157 (13)	−0.0856 (18)	0.052 (5)*
H13	1.4370 (18)	0.3751 (16)	0.116 (2)	0.069 (6)*
H10	1.3326 (17)	0.1481 (15)	−0.163 (2)	0.064 (6)*
H27	1.0675 (17)	0.0693 (16)	−0.001 (2)	0.069 (6)*
H14	1.2919 (17)	0.2952 (15)	0.123 (2)	0.067 (6)*
H28	1.131 (2)	0.1912 (18)	0.249 (2)	0.076 (7)*
H11	1.4793 (19)	0.2228 (16)	−0.164 (2)	0.076 (7)*
H22	1.639 (2)	0.509 (2)	0.055 (3)	0.088 (8)*
H5	0.945 (2)	0.249 (2)	0.327 (3)	0.094 (9)*
H20	1.737 (2)	0.3775 (17)	−0.064 (2)	0.076 (7)*
H16	1.446 (2)	0.3934 (18)	−0.237 (2)	0.085 (8)*
H1	1.157 (3)	0.057 (2)	0.454 (3)	0.116 (10)*
H26	1.631 (2)	0.259 (2)	0.162 (3)	0.099 (9)*
H23	1.743 (2)	0.545 (2)	0.249 (3)	0.100 (9)*
H4	0.893 (3)	0.242 (3)	0.507 (3)	0.127 (12)*
H3	0.970 (3)	0.139 (2)	0.657 (3)	0.110 (10)*
H17	1.486 (2)	0.4377 (19)	−0.416 (3)	0.095 (9)*
H25	1.729 (2)	0.295 (2)	0.356 (3)	0.114 (10)*
H18	1.650 (3)	0.453 (2)	−0.425 (3)	0.123 (11)*
H24	1.793 (3)	0.435 (2)	0.402 (3)	0.117 (10)*
H2	1.094 (3)	0.047 (3)	0.627 (4)	0.156 (15)*
H19	1.776 (3)	0.418 (2)	−0.242 (3)	0.115 (11)*

	U11	U22	U33	U12	U13	U23
S1	0.0620 (3)	0.0902 (4)	0.0645 (3)	−0.0305 (3)	0.0346 (3)	−0.0166 (2)
N2	0.0435 (8)	0.0544 (9)	0.0571 (9)	−0.0051 (6)	0.0197 (7)	0.0061 (6)
N3	0.0470 (8)	0.0611 (9)	0.0538 (9)	−0.0103 (6)	0.0227 (7)	0.0001 (7)
N4	0.0621 (10)	0.0633 (10)	0.0595 (10)	−0.0172 (8)	0.0291 (8)	−0.0071 (7)
N1	0.0513 (9)	0.0729 (11)	0.0580 (10)	−0.0204 (7)	0.0194 (7)	0.0007 (7)
C8	0.0469 (10)	0.0628 (11)	0.0496 (10)	−0.0083 (8)	0.0181 (8)	0.0027 (8)
C14	0.0495 (10)	0.0655 (11)	0.0478 (10)	−0.0069 (8)	0.0208 (8)	−0.0009 (8)
C9	0.0435 (9)	0.0603 (10)	0.0457 (9)	−0.0073 (7)	0.0158 (7)	0.0046 (7)
C7	0.0456 (10)	0.0591 (11)	0.0518 (10)	−0.0002 (7)	0.0187 (8)	0.0028 (7)
C12	0.0446 (9)	0.0591 (10)	0.0511 (10)	−0.0118 (7)	0.0164 (8)	0.0016 (7)
C13	0.0527 (11)	0.0601 (11)	0.0504 (10)	−0.0097 (8)	0.0180 (8)	−0.0041 (8)
C15	0.0517 (10)	0.0556 (10)	0.0659 (12)	−0.0092 (8)	0.0274 (9)	0.0009 (8)
C11	0.0612 (12)	0.0715 (13)	0.0593 (12)	−0.0200 (9)	0.0315 (10)	−0.0112 (9)
C10	0.0605 (12)	0.0674 (12)	0.0533 (11)	−0.0206 (9)	0.0244 (9)	−0.0099 (9)
C6	0.0601 (11)	0.0618 (11)	0.0555 (11)	−0.0156 (8)	0.0248 (9)	−0.0101 (8)
C21	0.0446 (10)	0.0610 (11)	0.0626 (11)	−0.0097 (8)	0.0141 (8)	0.0007 (8)
C20	0.0556 (13)	0.0799 (15)	0.0902 (17)	−0.0125 (10)	0.0380 (13)	−0.0069 (12)
C5	0.0682 (14)	0.0901 (17)	0.0703 (15)	0.0024 (12)	0.0241 (12)	−0.0077 (12)
C16	0.0648 (14)	0.0816 (15)	0.0711 (14)	−0.0047 (11)	0.0274 (11)	0.0119 (11)
C22	0.0681 (14)	0.0619 (13)	0.0732 (14)	−0.0122 (10)	0.0160 (11)	−0.0012 (10)
C3	0.109 (2)	0.100 (2)	0.0674 (16)	−0.0263 (16)	0.0463 (16)	−0.0164 (14)
C1	0.109 (2)	0.0796 (16)	0.0722 (15)	0.0111 (14)	0.0446 (14)	0.0038 (11)
C19	0.088 (2)	0.100 (2)	0.125 (3)	−0.0330 (16)	0.071 (2)	−0.0205 (18)
C23	0.0795 (17)	0.0834 (18)	0.0887 (18)	−0.0274 (13)	0.0189 (13)	−0.0199 (14)
C17	0.111 (2)	0.0909 (19)	0.0725 (17)	−0.0087 (15)	0.0344 (16)	0.0171 (13)
C18	0.133 (3)	0.097 (2)	0.094 (2)	−0.0332 (18)	0.070 (2)	0.0010 (16)
C26	0.0736 (15)	0.0710 (15)	0.0876 (17)	−0.0168 (12)	−0.0056 (12)	0.0146 (12)
C2	0.144 (3)	0.097 (2)	0.0718 (17)	0.0073 (19)	0.0487 (18)	0.0130 (14)
C4	0.0747 (17)	0.111 (2)	0.0872 (19)	−0.0094 (15)	0.0392 (15)	−0.0299 (16)
C24	0.0808 (18)	0.124 (3)	0.0789 (18)	−0.0342 (17)	−0.0022 (14)	−0.0033 (16)
C25	0.097 (2)	0.111 (2)	0.091 (2)	−0.0268 (17)	−0.0221 (16)	0.0267 (17)

S1—C7	1.6757 (19)	C21—C26	1.378 (3)
N2—C8	1.286 (2)	C21—C22	1.380 (3)
N2—N3	1.372 (2)	C20—C19	1.380 (4)
N3—C7	1.345 (2)	C20—H20	0.94 (3)
N3—N2	1.372 (2)	C5—C4	1.399 (4)
N3—H27	0.98 (2)	C5—H5	0.94 (3)
N4—C7	1.333 (2)	C16—C17	1.382 (3)
N4—C6	1.436 (2)	C16—H16	0.92 (3)
N4—H28	0.88 (3)	C22—C23	1.381 (4)
N1—C12	1.413 (2)	C22—H22	0.96 (3)
N1—C15	1.416 (2)	C3—C4	1.357 (5)
N1—C21	1.425 (3)	C3—C2	1.362 (5)
C8—N2	1.286 (2)	C3—H3	0.92 (4)
C8—C9	1.458 (2)	C1—C2	1.381 (4)
C8—H8	1.02 (2)	C1—H1	1.04 (4)
C14—C13	1.376 (3)	C19—C18	1.354 (5)
C14—C9	1.390 (3)	C19—H19	0.87 (4)
C14—H14	0.98 (2)	C23—C24	1.368 (4)
C9—C10	1.391 (3)	C23—H23	0.95 (3)
C12—C11	1.387 (3)	C17—C18	1.373 (5)
C12—C13	1.392 (3)	C17—H17	0.98 (3)
C13—H13	0.96 (2)	C18—H18	0.99 (4)
C15—C16	1.381 (3)	C26—C25	1.385 (4)
C15—C20	1.387 (3)	C26—H26	0.97 (3)
C11—C10	1.386 (3)	C2—H2	0.99 (5)
C11—H11	0.97 (3)	C4—H4	0.94 (4)
C10—H10	0.95 (2)	C24—C25	1.356 (5)
C6—C1	1.368 (4)	C24—H24	1.01 (3)
C6—C5	1.370 (3)	C25—H25	0.97 (4)
C8—N2—N3	115.86 (16)	C19—C20—H20	121.7 (17)
C7—N3—N2	119.97 (16)	C15—C20—H20	118.5 (17)
C7—N3—H27	121.1 (14)	C6—C5—C4	118.7 (3)
N2—N3—H27	118.4 (14)	C6—C5—H5	118.7 (18)
C7—N4—C6	123.82 (16)	C4—C5—H5	122.6 (18)
C7—N4—H28	114.7 (17)	C15—C16—C17	120.7 (3)
C6—N4—H28	121.1 (17)	C15—C16—H16	118.7 (17)
C12—N1—C15	121.79 (16)	C17—C16—H16	120.6 (17)
C12—N1—C21	118.09 (15)	C21—C22—C23	120.4 (2)
C15—N1—C21	120.11 (15)	C21—C22—H22	118.8 (17)
N2—C8—C9	121.06 (17)	C23—C22—H22	120.8 (17)
N2—C8—H8	119.9 (11)	C4—C3—C2	120.3 (3)
C9—C8—H8	119.0 (11)	C4—C3—H3	121 (2)
C13—C14—C9	120.91 (18)	C2—C3—H3	118 (2)
C13—C14—H14	118.7 (13)	C6—C1—C2	119.6 (3)
C9—C14—H14	120.3 (13)	C6—C1—H1	125.0 (19)
C14—C9—C10	118.33 (16)	C2—C1—H1	115.3 (19)
C14—C9—C8	121.71 (17)	C18—C19—C20	121.6 (3)
C10—C9—C8	119.95 (17)	C18—C19—H19	120 (2)
N4—C7—N3	116.64 (16)	C20—C19—H19	118 (2)
N4—C7—S1	123.79 (14)	C24—C23—C22	120.4 (3)
N3—C7—S1	119.57 (14)	C24—C23—H23	118.0 (18)
C11—C12—C13	118.91 (16)	C22—C23—H23	121.4 (18)
C11—C12—N1	121.55 (17)	C18—C17—C16	120.3 (3)
C13—C12—N1	119.53 (17)	C18—C17—H17	121.6 (18)
C14—C13—C12	120.66 (18)	C16—C17—H17	118.1 (18)
C14—C13—H13	120.6 (14)	C19—C18—C17	119.2 (3)
C12—C13—H13	118.7 (14)	C19—C18—H18	128 (2)
C16—C15—C20	118.5 (2)	C17—C18—H18	113 (2)
C16—C15—N1	121.41 (18)	C21—C26—C25	119.8 (3)
C20—C15—N1	120.1 (2)	C21—C26—H26	117.1 (18)
C10—C11—C12	120.20 (19)	C25—C26—H26	122.9 (18)
C10—C11—H11	117.2 (14)	C3—C2—C1	120.2 (3)
C12—C11—H11	122.3 (14)	C3—C2—H2	120 (3)
C11—C10—C9	120.97 (18)	C1—C2—H2	119 (3)
C11—C10—H10	119.6 (14)	C3—C4—C5	120.4 (3)
C9—C10—H10	119.4 (14)	C3—C4—H4	124 (2)
C1—C6—C5	120.8 (2)	C5—C4—H4	116 (2)
C1—C6—N4	118.9 (2)	C25—C24—C23	119.4 (3)
C5—C6—N4	120.3 (2)	C25—C24—H24	116 (2)
C26—C21—C22	118.8 (2)	C23—C24—H24	125 (2)
C26—C21—N1	120.42 (19)	C24—C25—C26	121.2 (3)
C22—C21—N1	120.73 (19)	C24—C25—H25	123 (2)
C19—C20—C15	119.8 (3)	C26—C25—H25	116 (2)
C8—N2—N3—C7	175.71 (17)	C7—N4—C6—C1	85.9 (3)
N3—N2—C8—C9	179.95 (16)	C7—N4—C6—C5	−94.6 (3)
C13—C14—C9—C10	−0.8 (3)	C12—N1—C21—C26	46.8 (3)
C13—C14—C9—C8	178.35 (18)	C15—N1—C21—C26	−132.2 (2)
N2—C8—C9—C14	−11.5 (3)	C12—N1—C21—C22	−132.1 (2)
N2—C8—C9—C14	−11.5 (3)	C15—N1—C21—C22	48.9 (3)
N2—C8—C9—C10	167.58 (19)	C16—C15—C20—C19	0.5 (4)
N2—C8—C9—C10	167.58 (19)	N1—C15—C20—C19	−178.8 (2)
C6—N4—C7—N3	−173.22 (18)	C1—C6—C5—C4	−0.7 (4)
C6—N4—C7—S1	7.0 (3)	N4—C6—C5—C4	179.8 (2)
N2—N3—C7—N4	3.5 (3)	C20—C15—C16—C17	0.3 (4)
N2—N3—C7—N4	3.5 (3)	N1—C15—C16—C17	179.7 (2)
N2—N3—C7—S1	−176.74 (13)	C26—C21—C22—C23	1.1 (4)
N2—N3—C7—S1	−176.74 (13)	N1—C21—C22—C23	−179.9 (2)
C15—N1—C12—C11	39.0 (3)	C5—C6—C1—C2	−0.1 (4)
C21—N1—C12—C11	−139.9 (2)	N4—C6—C1—C2	179.4 (3)
C15—N1—C12—C13	−141.7 (2)	C15—C20—C19—C18	−1.1 (4)
C21—N1—C12—C13	39.3 (3)	C21—C22—C23—C24	−1.0 (4)
C9—C14—C13—C12	−0.4 (3)	C15—C16—C17—C18	−0.7 (4)
C11—C12—C13—C14	1.0 (3)	C20—C19—C18—C17	0.8 (5)
N1—C12—C13—C14	−178.29 (18)	C16—C17—C18—C19	0.1 (5)
C12—N1—C15—C16	31.7 (3)	C22—C21—C26—C25	0.3 (4)
C21—N1—C15—C16	−149.4 (2)	N1—C21—C26—C25	−178.6 (3)
C12—N1—C15—C20	−149.0 (2)	C4—C3—C2—C1	−3.0 (5)
C21—N1—C15—C20	30.0 (3)	C6—C1—C2—C3	1.9 (5)
C13—C12—C11—C10	−0.4 (3)	C2—C3—C4—C5	2.2 (5)
N1—C12—C11—C10	178.82 (19)	C6—C5—C4—C3	−0.3 (4)
C12—C11—C10—C9	−0.7 (3)	C22—C23—C24—C25	−0.5 (5)
C14—C9—C10—C11	1.3 (3)	C23—C24—C25—C26	2.0 (6)
C8—C9—C10—C11	−177.8 (2)	C21—C26—C25—C24	−2.0 (6)

D—H···A	D—H	H···A	D···A	D—H···A
N4—H28···N2	0.88 (3)	2.19 (3)	2.629 (2)	110 (2)
N3—H27···S1i	0.98 (2)	2.36 (3)	3.318 (2)	169 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N4—H28⋯N2	0.88 (3)	2.19 (3)	2.629 (2)	110 (2)
N3—H27⋯S1i	0.98 (2)	2.36 (3)	3.318 (2)	169 (2)

Symmetry code: (i) .