Literature DB >> 21201402

4,4-Bis(4-methyl-phenyl-sulfan-yl)-1,1-diphenyl-2-aza-buta-1,3-diene.

Rodolphe Kinghat, Hamid Boudiba, Abderrahim Khatyr, Michael Knorr, Marek M Kubicki.

Abstract

In the title compound, C(29)H(25)NS(2), both the Cl atoms of the aza-diene precursor 4,4-dichloro-1,1-diphenyl-2-aza-buta-1,3-diene are replaced by two vicinal S-p-tolyl substituents attached to the terminal C atom of a π-conjugated 2-aza-butadiene array. The aza-diene chain is planar to within 0.01 Å. One of the phenyl rings seems to be slightly π-conjugated with the aza-diene core [dihedral angle 5.1 (2)°].

Entities: CellLine Chemical Disease Gene

Year: 2008 PMID： 21201402 PMCID： PMC2960289 DOI： 10.1107/S1600536807066615

Source DB: PubMed Journal: Acta Crystallogr Sect E Struct Rep Online ISSN： 1600-5368

Related literature

Some related structures of alkoxo- (Jacquot et al., 2000 ▶), cyano- (Jacquot-Rousseau et al., 2002 ▶) and PrS-substituted (Jacquot-Rousseau et al., 2005 ▶) 4,4-dichloro-1,1-diphenyl-2-azabuta-1,3-dienes (Jacquot et al., 1999 ▶) have been reported. For related literature, see: Tanimoto et al. (1976 ▶); Truce & Boudakian (1956 ▶).

Experimental

Crystal data

C29H25NS2 M = 451.66 Triclinic, a = 6.9340 (10) Å b = 12.3009 (2) Å c = 14.4247 (3) Å α = 101.7371 (8)° β = 98.2522 (7)° γ = 93.0400 (10)° V = 1187.90 (4) Å3 Z = 2 Mo Kα radiation μ = 0.24 mm−1 T = 120 (2) K 0.2 × 0.12 × 0.08 mm

Data collection

Nonius KappaCCD diffractometer Absorption correction: none 7710 measured reflections 5329 independent reflections 4695 reflections with I > 2σ(I) R int = 0.019

Refinement

R[F 2 > 2σ(F 2)] = 0.034 wR(F 2) = 0.089 S = 1.04 5329 reflections 317 parameters H atoms treated by a mixture of independent and constrained refinement Δρmax = 0.27 e Å−3 Δρmin = −0.24 e Å−3 Data collection: KappaCCD Server Software (Nonius, 1997 ▶); cell refinement: SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: DENZO (Otwinowski & Minor, 1997 ▶) and SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97. Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536807066615/gw2031sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536807066615/gw2031Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C₂₉H₂₅NS₂	Z = 2
M_r = 451.66	F₀₀₀ = 476
Triclinic, P1	D_x = 1.263 Mg m⁻³
Hall symbol: -P 1	Melting point: 382 K
a = 6.9340 (10) Å	Mo Kα radiation λ = 0.71073 Å
b = 12.3009 (2) Å	Cell parameters from 3954 reflections
c = 14.4247 (3) Å	θ = 1.0–27.5º
α = 101.7371 (8)º	µ = 0.24 mm⁻¹
β = 98.2522 (7)º	T = 120 (2) K
γ = 93.0400 (10)º	Irregular, yellow
V = 1187.90 (4) Å³	0.2 × 0.12 × 0.08 mm

Nonius KappaCCD diffractometer	4695 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.019
Monochromator: graphite	θ_max = 27.4º
T = 120(2) K	θ_min = 1.5º
CCD scans	h = −8→8
Absorption correction: none	k = −12→15
7710 measured reflections	l = −18→18
5329 independent reflections

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.034	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.089	w = 1/[σ²(F_o²) + (0.0329P)² + 0.5208P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max = 0.001
5329 reflections	Δρ_max = 0.27 e Å⁻³
317 parameters	Δρ_min = −0.24 e Å⁻³
Primary atom site location: structure-invariant direct methods	Extinction correction: none

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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 > σ(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	U_iso*/U_eq
S1	0.22781 (5)	0.37867 (3)	0.35024 (2)	0.02290 (9)
S2	0.43297 (4)	0.52776 (3)	0.23783 (2)	0.02161 (9)
N	0.48657 (16)	0.21771 (9)	0.26950 (8)	0.0221 (2)
C1	0.58163 (18)	0.13424 (11)	0.23639 (9)	0.0204 (3)
C2	0.50043 (19)	0.31661 (11)	0.23787 (10)	0.0227 (3)
C3	0.39300 (18)	0.40002 (11)	0.27163 (9)	0.0200 (3)
C4	0.71038 (19)	0.13495 (10)	0.16171 (9)	0.0206 (3)
C5	0.6304 (2)	0.12895 (14)	0.06658 (11)	0.0328 (3)
H5	0.4953	0.1238	0.0489	0.039*
C6	0.7506 (3)	0.13066 (16)	−0.00219 (12)	0.0415 (4)
H6	0.6960	0.1270	−0.0656	0.050*
C7	0.9508 (2)	0.13778 (14)	0.02340 (12)	0.0364 (4)
H7	1.0312	0.1378	−0.0230	0.044*
C8	1.0317 (2)	0.14488 (13)	0.11728 (12)	0.0350 (3)
H8	1.1670	0.1506	0.1345	0.042*
C9	0.9128 (2)	0.14354 (12)	0.18644 (11)	0.0287 (3)
H9	0.9686	0.1484	0.2499	0.034*
C10	0.56071 (18)	0.03303 (11)	0.27658 (9)	0.0207 (3)
C11	0.6700 (2)	−0.05758 (11)	0.25308 (10)	0.0250 (3)
H11	0.7553	−0.0568	0.2089	0.030*
C12	0.6528 (2)	−0.14933 (12)	0.29507 (11)	0.0293 (3)
H12	0.7284	−0.2087	0.2799	0.035*
C13	0.5238 (2)	−0.15238 (12)	0.35923 (11)	0.0285 (3)
H13	0.5126	−0.2136	0.3874	0.034*
C14	0.4112 (2)	−0.06400 (13)	0.38151 (12)	0.0322 (3)
H14	0.3228	−0.0664	0.4240	0.039*
C15	0.4296 (2)	0.02781 (12)	0.34092 (11)	0.0290 (3)
H15	0.3537	0.0869	0.3566	0.035*
C16	0.19592 (18)	0.55484 (11)	0.18701 (9)	0.0200 (3)
C17	0.05190 (19)	0.47143 (11)	0.13858 (10)	0.0231 (3)
H17	0.0744	0.3969	0.1344	0.028*
C18	−0.1256 (2)	0.50030 (12)	0.09652 (10)	0.0258 (3)
H18	−0.2222	0.4443	0.0652	0.031*
C19	−0.1623 (2)	0.61123 (12)	0.10010 (10)	0.0249 (3)
C20	−0.0167 (2)	0.69289 (12)	0.14901 (10)	0.0269 (3)
H20	−0.0387	0.7675	0.1528	0.032*
C21	0.1609 (2)	0.66593 (11)	0.19237 (10)	0.0255 (3)
H21	0.2563	0.7221	0.2249	0.031*
C22	−0.3522 (2)	0.64249 (15)	0.05100 (12)	0.0328 (3)
C23	0.16434 (19)	0.51460 (10)	0.39797 (9)	0.0195 (3)
C24	−0.02989 (19)	0.53814 (11)	0.38031 (9)	0.0217 (3)
H24	−0.1223	0.4848	0.3408	0.026*
C25	−0.08547 (19)	0.64104 (11)	0.42158 (10)	0.0233 (3)
H25	−0.2158	0.6559	0.4098	0.028*
C26	0.0502 (2)	0.72288 (11)	0.48054 (9)	0.0222 (3)
C27	0.2438 (2)	0.69758 (11)	0.49862 (9)	0.0231 (3)
H27	0.3362	0.7509	0.5383	0.028*
C28	0.30109 (19)	0.59443 (11)	0.45858 (9)	0.0218 (3)
H28	0.4305	0.5786	0.4721	0.026*
C29	−0.0105 (3)	0.83537 (13)	0.52391 (12)	0.0316 (3)
H2	0.587 (2)	0.3271 (13)	0.1916 (11)	0.023 (4)*
H221	−0.460 (3)	0.6112 (18)	0.0711 (16)	0.060 (6)*
H222	−0.370 (3)	0.6152 (19)	−0.0180 (18)	0.065 (7)*
H223	−0.357 (3)	0.722 (2)	0.0618 (17)	0.075 (7)*
H291	−0.049 (3)	0.8755 (17)	0.4753 (15)	0.050 (5)*
H292	0.094 (3)	0.8815 (18)	0.5682 (15)	0.055 (6)*
H293	−0.120 (3)	0.8270 (19)	0.5548 (16)	0.066 (7)*

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.02781 (18)	0.01708 (16)	0.02706 (18)	0.00498 (12)	0.01078 (13)	0.00695 (13)
S2	0.01964 (16)	0.02080 (17)	0.02704 (18)	0.00391 (12)	0.00537 (12)	0.00951 (13)
N	0.0233 (5)	0.0201 (5)	0.0235 (6)	0.0061 (4)	0.0038 (4)	0.0045 (4)
C1	0.0199 (6)	0.0198 (6)	0.0200 (6)	0.0040 (5)	0.0010 (5)	0.0021 (5)
C2	0.0229 (6)	0.0226 (6)	0.0235 (7)	0.0053 (5)	0.0042 (5)	0.0059 (5)
C3	0.0207 (6)	0.0193 (6)	0.0206 (6)	0.0035 (5)	0.0028 (5)	0.0056 (5)
C4	0.0235 (6)	0.0162 (6)	0.0228 (6)	0.0048 (5)	0.0053 (5)	0.0037 (5)
C5	0.0273 (7)	0.0471 (9)	0.0257 (7)	0.0121 (6)	0.0035 (6)	0.0095 (7)
C6	0.0454 (9)	0.0584 (11)	0.0255 (8)	0.0162 (8)	0.0095 (7)	0.0144 (7)
C7	0.0398 (9)	0.0389 (9)	0.0375 (9)	0.0084 (7)	0.0209 (7)	0.0126 (7)
C8	0.0250 (7)	0.0377 (8)	0.0433 (9)	−0.0011 (6)	0.0105 (6)	0.0080 (7)
C9	0.0258 (7)	0.0311 (7)	0.0268 (7)	−0.0012 (6)	0.0014 (6)	0.0035 (6)
C10	0.0217 (6)	0.0198 (6)	0.0197 (6)	0.0033 (5)	0.0022 (5)	0.0023 (5)
C11	0.0285 (7)	0.0229 (7)	0.0259 (7)	0.0064 (5)	0.0090 (5)	0.0056 (5)
C12	0.0346 (8)	0.0218 (7)	0.0345 (8)	0.0089 (6)	0.0100 (6)	0.0077 (6)
C13	0.0342 (7)	0.0225 (7)	0.0306 (8)	0.0016 (6)	0.0057 (6)	0.0095 (6)
C14	0.0349 (8)	0.0300 (8)	0.0360 (8)	0.0042 (6)	0.0166 (6)	0.0093 (6)
C15	0.0305 (7)	0.0251 (7)	0.0351 (8)	0.0092 (6)	0.0137 (6)	0.0070 (6)
C16	0.0212 (6)	0.0232 (6)	0.0190 (6)	0.0062 (5)	0.0068 (5)	0.0087 (5)
C17	0.0270 (7)	0.0213 (6)	0.0227 (7)	0.0051 (5)	0.0055 (5)	0.0064 (5)
C18	0.0252 (7)	0.0292 (7)	0.0233 (7)	0.0024 (5)	0.0025 (5)	0.0072 (6)
C19	0.0240 (7)	0.0330 (7)	0.0224 (7)	0.0093 (5)	0.0078 (5)	0.0123 (6)
C20	0.0304 (7)	0.0232 (7)	0.0320 (8)	0.0095 (5)	0.0087 (6)	0.0131 (6)
C21	0.0260 (7)	0.0218 (7)	0.0300 (7)	0.0026 (5)	0.0052 (6)	0.0079 (5)
C22	0.0273 (8)	0.0437 (9)	0.0318 (8)	0.0108 (7)	0.0044 (6)	0.0166 (7)
C23	0.0243 (6)	0.0185 (6)	0.0183 (6)	0.0044 (5)	0.0066 (5)	0.0070 (5)
C24	0.0220 (6)	0.0224 (6)	0.0209 (6)	0.0011 (5)	0.0037 (5)	0.0049 (5)
C25	0.0212 (6)	0.0270 (7)	0.0244 (7)	0.0069 (5)	0.0068 (5)	0.0084 (5)
C26	0.0287 (7)	0.0217 (6)	0.0188 (6)	0.0058 (5)	0.0088 (5)	0.0057 (5)
C27	0.0269 (7)	0.0222 (6)	0.0196 (6)	0.0000 (5)	0.0025 (5)	0.0047 (5)
C28	0.0205 (6)	0.0243 (6)	0.0226 (6)	0.0040 (5)	0.0031 (5)	0.0092 (5)
C29	0.0381 (8)	0.0249 (7)	0.0323 (8)	0.0083 (6)	0.0112 (7)	0.0021 (6)

S1—C3	1.7689 (13)	C14—H14	0.9300
S1—C23	1.7776 (13)	C15—H15	0.9300
S2—C3	1.7572 (13)	C16—C21	1.3892 (19)
S2—C16	1.7781 (13)	C16—C17	1.3919 (19)
N—C1	1.2959 (17)	C17—C18	1.3890 (19)
N—C2	1.3869 (17)	C17—H17	0.9300
C1—C10	1.4851 (18)	C18—C19	1.393 (2)
C1—C4	1.4955 (18)	C18—H18	0.9300
C2—C3	1.3515 (18)	C19—C20	1.388 (2)
C2—H2	0.983 (15)	C19—C22	1.5098 (19)
C4—C9	1.3904 (19)	C20—C21	1.3873 (19)
C4—C5	1.3902 (19)	C20—H20	0.9300
C5—C6	1.387 (2)	C21—H21	0.9300
C5—H5	0.9300	C22—H221	0.93 (2)
C6—C7	1.378 (2)	C22—H222	0.97 (2)
C6—H6	0.9300	C22—H223	0.96 (3)
C7—C8	1.373 (2)	C23—C24	1.3912 (18)
C7—H7	0.9300	C23—C28	1.3936 (18)
C8—C9	1.385 (2)	C24—C25	1.3843 (19)
C8—H8	0.9300	C24—H24	0.9300
C9—H9	0.9300	C25—C26	1.3941 (19)
C10—C11	1.3934 (18)	C25—H25	0.9300
C10—C15	1.3974 (19)	C26—C27	1.3942 (19)
C11—C12	1.3927 (19)	C26—C29	1.5062 (19)
C11—H11	0.9300	C27—C28	1.3864 (19)
C12—C13	1.381 (2)	C27—H27	0.9300
C12—H12	0.9300	C28—H28	0.9300
C13—C14	1.384 (2)	C29—H291	0.95 (2)
C13—H13	0.9300	C29—H292	0.97 (2)
C14—C15	1.382 (2)	C29—H293	0.95 (2)

C3—S1—C23	104.31 (6)	C21—C16—C17	119.68 (12)
C3—S2—C16	103.68 (6)	C21—C16—S2	116.76 (10)
C1—N—C2	121.26 (12)	C17—C16—S2	123.46 (10)
N—C1—C10	117.10 (12)	C18—C17—C16	119.57 (12)
N—C1—C4	123.91 (12)	C18—C17—H17	120.2
C10—C1—C4	118.98 (11)	C16—C17—H17	120.2
C3—C2—N	119.27 (12)	C17—C18—C19	121.53 (13)
C3—C2—H2	119.6 (9)	C17—C18—H18	119.2
N—C2—H2	121.2 (9)	C19—C18—H18	119.2
C2—C3—S2	117.32 (10)	C20—C19—C18	117.82 (12)
C2—C3—S1	119.54 (10)	C20—C19—C22	120.64 (13)
S2—C3—S1	123.10 (8)	C18—C19—C22	121.53 (14)
C9—C4—C5	118.69 (13)	C21—C20—C19	121.59 (13)
C9—C4—C1	120.58 (12)	C21—C20—H20	119.2
C5—C4—C1	120.73 (12)	C19—C20—H20	119.2
C6—C5—C4	120.46 (14)	C20—C21—C16	119.80 (13)
C6—C5—H5	119.8	C20—C21—H21	120.1
C4—C5—H5	119.8	C16—C21—H21	120.1
C7—C6—C5	120.06 (15)	C19—C22—H221	111.6 (13)
C7—C6—H6	120.0	C19—C22—H222	111.9 (13)
C5—C6—H6	120.0	H221—C22—H222	105.5 (18)
C8—C7—C6	120.05 (14)	C19—C22—H223	111.4 (14)
C8—C7—H7	120.0	H221—C22—H223	109.5 (19)
C6—C7—H7	120.0	H222—C22—H223	106.6 (19)
C7—C8—C9	120.25 (14)	C24—C23—C28	119.57 (12)
C7—C8—H8	119.9	C24—C23—S1	118.78 (10)
C9—C8—H8	119.9	C28—C23—S1	121.44 (10)
C8—C9—C4	120.48 (14)	C25—C24—C23	119.96 (12)
C8—C9—H9	119.8	C25—C24—H24	120.0
C4—C9—H9	119.8	C23—C24—H24	120.0
C11—C10—C15	118.28 (12)	C24—C25—C26	121.25 (12)
C11—C10—C1	122.05 (12)	C24—C25—H25	119.4
C15—C10—C1	119.66 (12)	C26—C25—H25	119.4
C12—C11—C10	120.62 (13)	C27—C26—C25	118.15 (12)
C12—C11—H11	119.7	C27—C26—C29	120.85 (13)
C10—C11—H11	119.7	C25—C26—C29	121.01 (13)
C13—C12—C11	120.18 (13)	C28—C27—C26	121.20 (12)
C13—C12—H12	119.9	C28—C27—H27	119.4
C11—C12—H12	119.9	C26—C27—H27	119.4
C12—C13—C14	119.75 (13)	C27—C28—C23	119.84 (12)
C12—C13—H13	120.1	C27—C28—H28	120.1
C14—C13—H13	120.1	C23—C28—H28	120.1
C15—C14—C13	120.26 (14)	C26—C29—H291	110.6 (12)
C15—C14—H14	119.9	C26—C29—H292	112.6 (13)
C13—C14—H14	119.9	H291—C29—H292	106.3 (17)
C14—C15—C10	120.89 (13)	C26—C29—H293	110.2 (14)
C14—C15—H15	119.6	H291—C29—H293	106.8 (18)
C10—C15—H15	119.6	H292—C29—H293	110.1 (18)

1 in total

1. Crystal structure of 4,4-di-bromo-1-(3,4-di-meth-oxy-phen-yl)-2-aza-buta-1,3-diene-1-carbo-nitrile.

Authors: Marwa Chaabene; Abderrahim Khatyr; Michael Knorr; Moheddine Askri; Yoann Rousselin; Marek M Kubicki
Journal: Acta Crystallogr E Crystallogr Commun Date: 2016-07-22

1 in total