Crystal structure of 2-butyl­sulfanyl-4,6-bis­[(E)-4-(di­methyl­amino)­styr­yl]pyrimidine

Song, J.; Zhou, Q.; Wang, A.

doi:10.1107/S2056989015021441

organic compounds

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ISSN: 2056-9890

Volume 71| Part 12| December 2015| Page o978

https://doi.org/10.1107/S2056989015021441

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Crystal structure of 2-butylsulfanyl-4,6-bis[(E)-4-(dimethylamino)styryl]pyrimidine

Jingbao Song,^a Qiang Zhou ^a and Aijian Wang ^a ^*

^aChina-Australia Joint Research Center for Functional Molecular Materials, Scientific Research Academy, Jiangsu University, Zhenjiang 212013, People's Republic of China
^*Correspondence e-mail: wajujs@ujs.edu.cn

Edited by W. T. A. Harrison, University of Aberdeen, Scotland (Received 9 November 2015; accepted 12 November 2015; online 21 November 2015)

In the title compound, C₂₈H₃₄N₄S, the dihedral angles between the pyrimidine ring and the pendant 4-(dimethylamino)benzene rings are 14.20 (5) and 14.56 (4)°. The butyl side chain adopts an anti conformation [C—C—C—C = −171.53 (13)°]. No directional interactions beyond van der Waals contacts occur in the crystal structure The title molecule has a D–A–D structure, in which the pyrimidine ring is the electron-withdrawing part and the 4-(dimethylamino)benzene rings are the electron-donating parts.

Keywords: crystal structure; pyrimidine; D–A–D interaction.

CCDC reference: 1435236

1. Related literature

For general background to pyrimidine derivatives and their applications, see: Walker et al. (2009 ); van Laar et al. (2001 ); Deng et al. (2008 ); Nguyen (2008 ). For further synthetic details, see: Liu et al. (2007 ).

2. Experimental

2.1. Crystal data

C₂₈H₃₄N₄S
M_r = 458.65
Monoclinic, P 2₁ /c
a = 7.4425 (15) Å
b = 12.583 (3) Å
c = 27.448 (6) Å
β = 99.31 (3)°
V = 2536.6 (10) Å³
Z = 4
Mo Kα radiation
μ = 0.15 mm⁻¹
T = 293 K
0.20 × 0.20 × 0.20 mm

2.2. Data collection

Rigaku Saturn724+ CCD diffractometer
Absorption correction: multi-scan CrystalClear; Rigaku, 2008 ) T_min = 0.795, T_max = 1.000
12427 measured reflections
4822 independent reflections
4371 reflections with I > 2σ(I)
R_int = 0.021

2.3. Refinement

R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.104
S = 1.07
4822 reflections
303 parameters
H-atom parameters constrained
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.29 e Å⁻³

Data collection: CrystalClear (Rigaku, 2008); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015 ); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information

CCDC reference: 1435236

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: https://doi.org/10.1107/S2056989015021441/hb7541sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989015021441/hb7541Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2056989015021441/hb7541Isup3.docx

Supporting information file. DOI: https://doi.org/10.1107/S2056989015021441/hb7541Isup4.cdx

Supporting information file. DOI: https://doi.org/10.1107/S2056989015021441/hb7541Isup5.cml

checkCIF report

Related literature top

For general background to pyrimidine derivatives and their applications, see: Walker et al. (2009); van Laar et al. (2001); Deng et al. (2008); Nguyen (2008). For further synthetic details, see: Liu et al. (2007).

Structure description top

For general background to pyrimidine derivatives and their applications, see: Walker et al. (2009); van Laar et al. (2001); Deng et al. (2008); Nguyen (2008). For further synthetic details, see: Liu et al. (2007).

Computing details top

Data collection: CrystalClear (Rigaku, 2008); cell refinement: CrystalClear (Rigaku, 2008); data reduction: CrystalClear (Rigaku, 2008); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. The title compound.

2-Butylsulfanyl-4,6-bis[(E)-4-(dimethylamino)styryl]pyrimidine top

Crystal data top

C₂₈H₃₄N₄S	F(000) = 984
M_r = 458.65	D_x = 1.201 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 7.4425 (15) Å	Cell parameters from 8318 reflections
b = 12.583 (3) Å	θ = 3.9–28.7°
c = 27.448 (6) Å	µ = 0.15 mm⁻¹
β = 99.31 (3)°	T = 293 K
V = 2536.6 (10) Å³	Prism, colorless
Z = 4	0.20 × 0.20 × 0.20 mm

Data collection top

Rigaku Saturn724+ CCD diffractometer	4371 reflections with I > 2σ(I)
Detector resolution: 28.5714 pixels mm^-1	R_int = 0.021
dtprofit.ref scans	θ_max = 26.0°, θ_min = 4.0°
Absorption correction: multi-scan CrystalClear; Rigaku, 2008)	h = −8→9
T_min = 0.795, T_max = 1.000	k = −14→15
12427 measured reflections	l = −32→21
4822 independent reflections

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.041	H-atom parameters constrained
wR(F²) = 0.104	w = 1/[σ²(F_o²) + (0.0542P)² + 0.4771P] where P = (F_o² + 2F_c²)/3
S = 1.07	(Δ/σ)_max = 0.001
4822 reflections	Δρ_max = 0.17 e Å⁻³
303 parameters	Δρ_min = −0.29 e Å⁻³

Crystal data top

C₂₈H₃₄N₄S	V = 2536.6 (10) Å³
M_r = 458.65	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 7.4425 (15) Å	µ = 0.15 mm⁻¹
b = 12.583 (3) Å	T = 293 K
c = 27.448 (6) Å	0.20 × 0.20 × 0.20 mm
β = 99.31 (3)°

Data collection top

Rigaku Saturn724+ CCD diffractometer	4822 independent reflections
Absorption correction: multi-scan CrystalClear; Rigaku, 2008)	4371 reflections with I > 2σ(I)
T_min = 0.795, T_max = 1.000	R_int = 0.021
12427 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	0 restraints
wR(F²) = 0.104	H-atom parameters constrained
S = 1.07	Δρ_max = 0.17 e Å⁻³
4822 reflections	Δρ_min = −0.29 e Å⁻³
303 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
S1	0.26097 (5)	1.10814 (3)	0.80444 (2)	0.03105 (12)
N1	0.24791 (15)	0.95402 (9)	0.73631 (4)	0.0268 (3)
N2	0.35953 (16)	0.91412 (9)	0.82151 (4)	0.0275 (3)
N3	0.12735 (17)	0.58633 (10)	0.45410 (4)	0.0326 (3)
N4	0.75955 (18)	0.54619 (10)	1.07267 (5)	0.0361 (3)
C1	0.34216 (19)	0.77758 (11)	0.76064 (5)	0.0277 (3)
H1	0.3574	0.7068	0.7525	0.033*
C2	0.15843 (18)	0.62194 (11)	0.50181 (5)	0.0260 (3)
C3	0.23233 (18)	0.69834 (11)	0.60088 (5)	0.0258 (3)
C4	0.08957 (19)	0.72030 (11)	0.51535 (5)	0.0278 (3)
H4	0.0180	0.7611	0.4915	0.033*
C5	0.12613 (18)	0.75688 (11)	0.56307 (5)	0.0273 (3)
H5	0.0793	0.8223	0.5706	0.033*
C6	0.26230 (19)	0.56204 (11)	0.53969 (5)	0.0275 (3)
H6	0.3075	0.4960	0.5324	0.033*
C7	0.23083 (18)	0.82523 (11)	0.67185 (5)	0.0280 (3)
H7	0.1684	0.8759	0.6509	0.034*
C8	0.29778 (19)	0.59998 (11)	0.58746 (5)	0.0275 (3)
H8	0.3676	0.5588	0.6116	0.033*
C9	0.56244 (18)	0.75441 (11)	0.98657 (5)	0.0278 (3)
H9	0.5156	0.8226	0.9881	0.033*
C10	0.27343 (18)	0.73315 (11)	0.65182 (5)	0.0275 (3)
H10	0.3383	0.6850	0.6736	0.033*
C11	0.69693 (19)	0.59909 (11)	1.02945 (5)	0.0266 (3)
C12	0.27576 (18)	0.85130 (11)	0.72417 (5)	0.0259 (3)
C13	0.70746 (19)	0.55396 (11)	0.98288 (5)	0.0281 (3)
H13	0.7569	0.4864	0.9812	0.034*
C14	0.64582 (19)	0.60825 (11)	0.93992 (5)	0.0280 (3)
H14	0.6542	0.5763	0.9098	0.034*
C15	0.29105 (18)	0.97763 (11)	0.78419 (5)	0.0263 (3)
C16	0.46067 (18)	0.73921 (11)	0.84922 (5)	0.0283 (3)
H16	0.4841	0.6691	0.8416	0.034*
C17	0.62066 (19)	0.70111 (11)	1.03003 (5)	0.0288 (3)
H17	0.6094	0.7328	1.0600	0.035*
C18	0.38519 (18)	0.81161 (11)	0.80933 (5)	0.0262 (3)
C19	0.49716 (18)	0.77085 (11)	0.89650 (5)	0.0283 (3)
H19	0.4716	0.8418	0.9021	0.034*
C20	0.20267 (19)	1.29855 (11)	0.76013 (5)	0.0269 (3)
H20A	0.3254	1.3142	0.7764	0.032*
H20B	0.1200	1.3153	0.7830	0.032*
C21	0.2041 (2)	0.48648 (12)	0.44047 (6)	0.0353 (4)
H21A	0.3341	0.4882	0.4498	0.053*
H21B	0.1737	0.4764	0.4054	0.053*
H21C	0.1553	0.4290	0.4572	0.053*
C22	0.1885 (2)	1.18094 (11)	0.74790 (5)	0.0301 (3)
H22A	0.2656	1.1635	0.7237	0.036*
H22B	0.0639	1.1626	0.7343	0.036*
C23	0.0143 (2)	0.64497 (13)	0.41538 (6)	0.0393 (4)
H23A	−0.0994	0.6621	0.4257	0.059*
H23B	−0.0079	0.6024	0.3860	0.059*
H23C	0.0754	0.7093	0.4087	0.059*
C24	0.1577 (2)	1.36854 (12)	0.71461 (6)	0.0316 (3)
H24A	0.2276	1.3449	0.6897	0.038*
H24B	0.0296	1.3610	0.7011	0.038*
C25	0.57083 (18)	0.71020 (11)	0.94023 (5)	0.0257 (3)
C26	0.7276 (3)	0.58937 (14)	1.11936 (6)	0.0448 (4)
H26A	0.7862	0.6573	1.1247	0.067*
H26B	0.7764	0.5419	1.1456	0.067*
H26C	0.5991	0.5976	1.1188	0.067*
C27	0.1994 (2)	1.48477 (13)	0.72632 (7)	0.0441 (4)
H27A	0.1323	1.5080	0.7514	0.066*
H27B	0.1648	1.5266	0.6971	0.066*
H27C	0.3274	1.4931	0.7378	0.066*
C28	0.8384 (2)	0.44130 (12)	1.07180 (6)	0.0378 (4)
H28A	0.7500	0.3935	1.0544	0.057*
H28B	0.8745	0.4165	1.1050	0.057*
H28C	0.9429	0.4443	1.0554	0.057*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0411 (2)	0.0249 (2)	0.0253 (2)	0.00081 (15)	0.00000 (16)	−0.00120 (13)
N1	0.0254 (6)	0.0266 (6)	0.0281 (7)	−0.0005 (5)	0.0034 (5)	−0.0013 (5)
N2	0.0277 (6)	0.0266 (6)	0.0277 (6)	−0.0004 (5)	0.0030 (5)	0.0009 (5)
N3	0.0387 (7)	0.0337 (7)	0.0241 (6)	0.0033 (6)	0.0012 (5)	−0.0021 (5)
N4	0.0495 (8)	0.0314 (7)	0.0266 (7)	0.0039 (6)	0.0038 (6)	0.0023 (5)
C1	0.0287 (7)	0.0245 (7)	0.0302 (8)	0.0005 (6)	0.0057 (6)	−0.0008 (6)
C2	0.0244 (7)	0.0293 (7)	0.0247 (7)	−0.0035 (6)	0.0055 (5)	−0.0001 (6)
C3	0.0242 (7)	0.0275 (7)	0.0264 (7)	−0.0011 (6)	0.0058 (5)	0.0011 (6)
C4	0.0279 (7)	0.0279 (7)	0.0271 (7)	0.0022 (6)	0.0030 (6)	0.0052 (6)
C5	0.0289 (7)	0.0242 (7)	0.0293 (8)	0.0019 (6)	0.0060 (6)	0.0007 (6)
C6	0.0284 (7)	0.0250 (7)	0.0299 (8)	0.0015 (6)	0.0067 (6)	−0.0007 (6)
C7	0.0264 (7)	0.0295 (8)	0.0275 (7)	0.0012 (6)	0.0024 (6)	0.0015 (6)
C8	0.0280 (7)	0.0276 (8)	0.0265 (7)	0.0015 (6)	0.0032 (6)	0.0037 (6)
C9	0.0258 (7)	0.0247 (7)	0.0327 (8)	−0.0003 (6)	0.0042 (6)	−0.0036 (6)
C10	0.0251 (7)	0.0298 (8)	0.0273 (7)	−0.0001 (6)	0.0033 (5)	0.0022 (6)
C11	0.0247 (7)	0.0274 (7)	0.0277 (7)	−0.0034 (6)	0.0044 (6)	−0.0005 (6)
C12	0.0206 (7)	0.0286 (7)	0.0289 (8)	−0.0019 (6)	0.0050 (5)	−0.0024 (6)
C13	0.0285 (7)	0.0244 (7)	0.0317 (8)	0.0015 (6)	0.0056 (6)	−0.0020 (6)
C14	0.0282 (7)	0.0306 (8)	0.0255 (7)	0.0007 (6)	0.0057 (6)	−0.0041 (6)
C15	0.0230 (7)	0.0275 (7)	0.0281 (8)	−0.0026 (6)	0.0036 (5)	−0.0010 (6)
C16	0.0288 (7)	0.0269 (7)	0.0296 (8)	0.0003 (6)	0.0061 (6)	0.0017 (6)
C17	0.0309 (7)	0.0293 (8)	0.0268 (8)	−0.0010 (6)	0.0065 (6)	−0.0050 (6)
C18	0.0218 (7)	0.0289 (7)	0.0284 (7)	−0.0011 (6)	0.0060 (5)	0.0014 (6)
C19	0.0247 (7)	0.0278 (7)	0.0325 (8)	0.0001 (6)	0.0051 (6)	0.0009 (6)
C20	0.0264 (7)	0.0271 (7)	0.0269 (7)	0.0007 (6)	0.0038 (6)	−0.0003 (6)
C21	0.0400 (8)	0.0375 (9)	0.0292 (8)	0.0009 (7)	0.0079 (6)	−0.0060 (6)
C22	0.0342 (8)	0.0293 (8)	0.0254 (7)	−0.0024 (6)	0.0002 (6)	−0.0005 (6)
C23	0.0493 (9)	0.0411 (9)	0.0253 (8)	0.0017 (8)	−0.0004 (7)	0.0002 (7)
C24	0.0293 (8)	0.0347 (8)	0.0311 (8)	0.0048 (6)	0.0059 (6)	0.0051 (6)
C25	0.0221 (7)	0.0274 (7)	0.0277 (7)	−0.0020 (6)	0.0043 (5)	−0.0006 (6)
C26	0.0611 (11)	0.0480 (10)	0.0251 (8)	0.0043 (8)	0.0066 (8)	0.0021 (7)
C27	0.0385 (9)	0.0329 (9)	0.0618 (12)	0.0038 (7)	0.0107 (8)	0.0122 (8)
C28	0.0381 (9)	0.0349 (9)	0.0406 (9)	0.0042 (7)	0.0068 (7)	0.0095 (7)

Geometric parameters (Å, º) top

S1—C15	1.7597 (15)	C13—C14	1.376 (2)
S1—C22	1.8076 (15)	C13—H13	0.9300
N1—C15	1.3348 (18)	C14—C25	1.400 (2)
N1—C12	1.3590 (18)	C14—H14	0.9300
N2—C15	1.3339 (18)	C16—C19	1.342 (2)
N2—C18	1.3538 (18)	C16—C18	1.4647 (19)
N3—C2	1.3679 (18)	C16—H16	0.9300
N3—C23	1.4463 (19)	C17—H17	0.9300
N3—C21	1.4539 (19)	C19—C25	1.4529 (19)
N4—C11	1.3742 (18)	C19—H19	0.9300
N4—C28	1.446 (2)	C20—C22	1.517 (2)
N4—C26	1.447 (2)	C20—C24	1.5211 (19)
C1—C18	1.391 (2)	C20—H20A	0.9700
C1—C12	1.395 (2)	C20—H20B	0.9700
C1—H1	0.9300	C21—H21A	0.9600
C2—C6	1.409 (2)	C21—H21B	0.9600
C2—C4	1.412 (2)	C21—H21C	0.9600
C3—C8	1.401 (2)	C22—H22A	0.9700
C3—C5	1.4069 (19)	C22—H22B	0.9700
C3—C10	1.450 (2)	C23—H23A	0.9600
C4—C5	1.373 (2)	C23—H23B	0.9600
C4—H4	0.9300	C23—H23C	0.9600
C5—H5	0.9300	C24—C27	1.519 (2)
C6—C8	1.380 (2)	C24—H24A	0.9700
C6—H6	0.9300	C24—H24B	0.9700
C7—C10	1.342 (2)	C26—H26A	0.9600
C7—C12	1.458 (2)	C26—H26B	0.9600
C7—H7	0.9300	C26—H26C	0.9600
C8—H8	0.9300	C27—H27A	0.9600
C9—C17	1.376 (2)	C27—H27B	0.9600
C9—C25	1.399 (2)	C27—H27C	0.9600
C9—H9	0.9300	C28—H28A	0.9600
C10—H10	0.9300	C28—H28B	0.9600
C11—C17	1.405 (2)	C28—H28C	0.9600
C11—C13	1.413 (2)

C15—S1—C22	103.73 (7)	C11—C17—H17	119.8
C15—N1—C12	115.53 (12)	N2—C18—C1	120.73 (13)
C15—N2—C18	115.65 (12)	N2—C18—C16	117.41 (13)
C2—N3—C23	121.63 (13)	C1—C18—C16	121.86 (13)
C2—N3—C21	121.11 (12)	C16—C19—C25	129.28 (14)
C23—N3—C21	117.25 (12)	C16—C19—H19	115.4
C11—N4—C28	120.65 (13)	C25—C19—H19	115.4
C11—N4—C26	120.10 (13)	C22—C20—C24	112.62 (12)
C28—N4—C26	118.85 (13)	C22—C20—H20A	109.1
C18—C1—C12	118.99 (13)	C24—C20—H20A	109.1
C18—C1—H1	120.5	C22—C20—H20B	109.1
C12—C1—H1	120.5	C24—C20—H20B	109.1
N3—C2—C6	121.25 (13)	H20A—C20—H20B	107.8
N3—C2—C4	121.79 (13)	N3—C21—H21A	109.5
C6—C2—C4	116.97 (13)	N3—C21—H21B	109.5
C8—C3—C5	116.50 (13)	H21A—C21—H21B	109.5
C8—C3—C10	119.50 (13)	N3—C21—H21C	109.5
C5—C3—C10	123.99 (13)	H21A—C21—H21C	109.5
C5—C4—C2	121.37 (13)	H21B—C21—H21C	109.5
C5—C4—H4	119.3	C20—C22—S1	107.68 (10)
C2—C4—H4	119.3	C20—C22—H22A	110.2
C4—C5—C3	121.95 (13)	S1—C22—H22A	110.2
C4—C5—H5	119.0	C20—C22—H22B	110.2
C3—C5—H5	119.0	S1—C22—H22B	110.2
C8—C6—C2	120.91 (13)	H22A—C22—H22B	108.5
C8—C6—H6	119.5	N3—C23—H23A	109.5
C2—C6—H6	119.5	N3—C23—H23B	109.5
C10—C7—C12	124.45 (13)	H23A—C23—H23B	109.5
C10—C7—H7	117.8	N3—C23—H23C	109.5
C12—C7—H7	117.8	H23A—C23—H23C	109.5
C6—C8—C3	122.29 (13)	H23B—C23—H23C	109.5
C6—C8—H8	118.9	C27—C24—C20	111.93 (13)
C3—C8—H8	118.9	C27—C24—H24A	109.2
C17—C9—C25	122.70 (13)	C20—C24—H24A	109.2
C17—C9—H9	118.6	C27—C24—H24B	109.2
C25—C9—H9	118.6	C20—C24—H24B	109.2
C7—C10—C3	128.96 (13)	H24A—C24—H24B	107.9
C7—C10—H10	115.5	C9—C25—C14	116.53 (13)
C3—C10—H10	115.5	C9—C25—C19	118.42 (13)
N4—C11—C17	120.94 (13)	C14—C25—C19	125.02 (13)
N4—C11—C13	121.72 (13)	N4—C26—H26A	109.5
C17—C11—C13	117.34 (13)	N4—C26—H26B	109.5
N1—C12—C1	120.46 (13)	H26A—C26—H26B	109.5
N1—C12—C7	115.82 (12)	N4—C26—H26C	109.5
C1—C12—C7	123.72 (13)	H26A—C26—H26C	109.5
C14—C13—C11	121.09 (13)	H26B—C26—H26C	109.5
C14—C13—H13	119.5	C24—C27—H27A	109.5
C11—C13—H13	119.5	C24—C27—H27B	109.5
C13—C14—C25	121.86 (13)	H27A—C27—H27B	109.5
C13—C14—H14	119.1	C24—C27—H27C	109.5
C25—C14—H14	119.1	H27A—C27—H27C	109.5
N2—C15—N1	128.61 (13)	H27B—C27—H27C	109.5
N2—C15—S1	111.65 (10)	N4—C28—H28A	109.5
N1—C15—S1	119.74 (11)	N4—C28—H28B	109.5
C19—C16—C18	122.09 (13)	H28A—C28—H28B	109.5
C19—C16—H16	119.0	N4—C28—H28C	109.5
C18—C16—H16	119.0	H28A—C28—H28C	109.5
C9—C17—C11	120.46 (13)	H28B—C28—H28C	109.5
C9—C17—H17	119.8

C23—N3—C2—C6	177.24 (14)	C17—C11—C13—C14	0.2 (2)
C21—N3—C2—C6	−1.5 (2)	C11—C13—C14—C25	0.2 (2)
C23—N3—C2—C4	−3.2 (2)	C18—N2—C15—N1	−1.5 (2)
C21—N3—C2—C4	177.99 (13)	C18—N2—C15—S1	179.25 (10)
N3—C2—C4—C5	−177.99 (13)	C12—N1—C15—N2	0.8 (2)
C6—C2—C4—C5	1.5 (2)	C12—N1—C15—S1	180.00 (10)
C2—C4—C5—C3	−0.5 (2)	C22—S1—C15—N2	174.93 (10)
C8—C3—C5—C4	−0.6 (2)	C22—S1—C15—N1	−4.41 (13)
C10—C3—C5—C4	−179.48 (13)	C25—C9—C17—C11	1.8 (2)
N3—C2—C6—C8	177.99 (13)	N4—C11—C17—C9	178.41 (13)
C4—C2—C6—C8	−1.5 (2)	C13—C11—C17—C9	−1.2 (2)
C2—C6—C8—C3	0.5 (2)	C15—N2—C18—C1	0.26 (19)
C5—C3—C8—C6	0.6 (2)	C15—N2—C18—C16	179.83 (12)
C10—C3—C8—C6	179.53 (13)	C12—C1—C18—N2	1.4 (2)
C12—C7—C10—C3	178.55 (13)	C12—C1—C18—C16	−178.11 (12)
C8—C3—C10—C7	177.03 (14)	C19—C16—C18—N2	2.6 (2)
C5—C3—C10—C7	−4.1 (2)	C19—C16—C18—C1	−177.88 (13)
C28—N4—C11—C17	−179.83 (13)	C18—C16—C19—C25	179.77 (13)
C26—N4—C11—C17	7.6 (2)	C24—C20—C22—S1	175.96 (10)
C28—N4—C11—C13	−0.3 (2)	C15—S1—C22—C20	−166.56 (10)
C26—N4—C11—C13	−172.87 (14)	C22—C20—C24—C27	−171.53 (13)
C15—N1—C12—C1	1.11 (19)	C17—C9—C25—C14	−1.3 (2)
C15—N1—C12—C7	−179.34 (12)	C17—C9—C25—C19	176.85 (13)
C18—C1—C12—N1	−2.2 (2)	C13—C14—C25—C9	0.3 (2)
C18—C1—C12—C7	178.32 (13)	C13—C14—C25—C19	−177.72 (13)
C10—C7—C12—N1	169.79 (13)	C16—C19—C25—C9	−167.16 (14)
C10—C7—C12—C1	−10.7 (2)	C16—C19—C25—C14	10.8 (2)
N4—C11—C13—C14	−179.37 (13)

Experimental details

Crystal data
Chemical formula	C₂₈H₃₄N₄S
M_r	458.65
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	7.4425 (15), 12.583 (3), 27.448 (6)
β (°)	99.31 (3)
V (Å³)	2536.6 (10)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.15
Crystal size (mm)	0.20 × 0.20 × 0.20

Data collection
Diffractometer	Rigaku Saturn724+ CCD
Absorption correction	Multi-scan CrystalClear; Rigaku, 2008)
T_min, T_max	0.795, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	12427, 4822, 4371
R_int	0.021
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.104, 1.07
No. of reflections	4822
No. of parameters	303
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.17, −0.29

Computer programs: CrystalClear (Rigaku, 2008), SHELXTL (Sheldrick, 2008), SHELXL2014 (Sheldrick, 2015).

Acknowledgements

This research was supported financially by the Research Foundation of Jiangsu University (grant No. 13JDG066).

References

Deng, Y., Wang, Y., Cherian, C., Hou, Z., Buck, S. A., Matherly, L. H. & Gangjee, A. (2008). J. Med. Chem. 51, 5052–5063. Web of Science CrossRef PubMed CAS Google Scholar
Laar, M. van, Volkerts, E. & Verbaten, M. (2001). Psychopharmacology, 154, 189–197. Web of Science PubMed Google Scholar
Liu, B., Hu, X., Liu, J., Zhao, Y. & Huang, Z. (2007). Tetrahedron Lett. 48, 5958–5962. Web of Science CrossRef CAS Google Scholar
Nguyen, T. L. (2008). Anticancer Agents Med. Chem. 8, 710–716. CrossRef PubMed CAS Google Scholar
Rigaku (2008). CrystalClear. Rigaku Corporation, Tokyo, Japan. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2015). Acta Cryst. C71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Walker, S. R., Carter, E. J., Huff, B. C. & Morris, J. C. (2009). Chem. Rev. 109, 3080–3098. Web of Science CrossRef PubMed CAS Google Scholar

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