2-{[4-(Dimethyl­amino)­benzyl­idene]amino}­phenyl disulfide

He, Q.-P.; Dai, L.; Tan, B.

doi:10.1107/S1600536811046277

organic compounds

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ISSN: 2056-9890

Volume 67| Part 12| December 2011| Page o3240

https://doi.org/10.1107/S1600536811046277

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2-{[4-(Dimethylamino)benzylidene]amino}phenyl disulfide

Qing-Peng He,^a ^* Li Dai ^b and Bo Tan ^a

^aCollege of Chemistry and Chemical Engineering, Liaocheng University, Shandong 252059, People's Republic of China, and ^bLiaocheng Bureau of Quality and Technical Supervision, Shandong 252059, People's Republic of China
^*Correspondence e-mail: heqp2008@163.com

(Received 26 October 2011; accepted 2 November 2011; online 9 November 2011)

In the title molecule, C₃₀H₃₀N₄S₂, the two benzene rings connected through the disulfide chain form a dihedral angle of 88.7 (1)°, and the two benzene rings in the benzylideneaniline fragments form dihedral angles of 34.0 (1) and 35.4 (1)°. The crystal packing exhibits no significantly short intermolecular contacts.

Related literature

For biological activity of Shiff base derivatives, see: Loncle et al. (2004 ); Li et al. (2004 ). For a related structure, see: Roy et al. (2009 ).

Experimental

Crystal data

C₃₀H₃₀N₄S₂
M_r = 510.70
Monoclinic, P 2₁ /n
a = 10.673 (1) Å
b = 22.906 (2) Å
c = 11.2939 (11) Å
β = 95.784 (1)°
V = 2747.0 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.22 mm⁻¹
T = 298 K
0.30 × 0.26 × 0.12 mm

Data collection

Bruker SMART APEX CCD area-etector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.937, T_max = 0.974
13873 measured reflections
4851 independent reflections
2145 reflections with I > 2σ(I)
R_int = 0.057

Refinement

R[F² > 2σ(F²)] = 0.051
wR(F²) = 0.122
S = 0.83
4851 reflections
329 parameters
H-atom parameters constrained
Δρ_max = 0.29 e Å⁻³
Δρ_min = −0.14 e Å⁻³

Data collection: SMART (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536811046277/cv5186sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811046277/cv5186Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536811046277/cv5186Isup3.cml

checkCIF report

Comment top

In recent years, a number of Schiff base derivatives were shown to exhibit a wide range of interesting biological activities, including antibacteriale antifungal, anticonvulsant, anticancer activities as well as herbicidal and fungicidal activity (Loncle et al., 2004; Li et al., 2004). As a part of our continuing interest in Schiff's bases contained imine N and anionic S atoms, we report here the crystal structure of the title compound (I).

In (I) (Fig. 1), the molecule has a trans configuration about the S—S bond. All bond lengths and angles are normal and comparable to those observed in similar compound 2,2'-(disulfanediylbis(2,1-phenylenenitrilomethylylidene)) bis(4,6-di-tbutylphenol) (Roy et al., 2009). Two benzene rings connected through disulfide chain form a dihedral angle of 88.7 (1)°, and two benzene rings in two benzylideneaniline fragments form the dihedral angles of 34.0 (1) and 35.4 (1)°, respectively. The crystal packing exhibits no significantly short intermolecular contacts.

Related literature top

For biological activity of Shiff base derivatives, see: Loncle et al. (2004); Li et al. (2004). For a related structure, see: Roy et al. (2009).

Experimental top

4-(Dimethylamino)benzaldehyde (6 mmol) and 2,2'-diaminodiphenyl disulfide (3 mmol) was refluxed in 20 ml of ethanol for 4.0 h, the mixture then cooling slowly to room temperature and affording the title compound, then recrystallized from ethanol, affording the title compound as a yellow crystalline solid.

Structure description top

For biological activity of Shiff base derivatives, see: Loncle et al. (2004); Li et al. (2004). For a related structure, see: Roy et al. (2009).

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. ORTEP drawing of the title complex with atomic numbering scheme and thermal ellipsoids at 30% probability level.

2-{[4-(Dimethylamino)benzylidene]amino}phenyl disulfide top

Crystal data top

C₃₀H₃₀N₄S₂	F(000) = 1080
M_r = 510.70	D_x = 1.235 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
a = 10.673 (1) Å	Cell parameters from 1564 reflections
b = 22.906 (2) Å	θ = 2.5–18.1°
c = 11.2939 (11) Å	µ = 0.22 mm⁻¹
β = 95.784 (1)°	T = 298 K
V = 2747.0 (4) Å³	Block, yellow
Z = 4	0.30 × 0.26 × 0.12 mm

Data collection top

Bruker SMART APEX CCD area-etector diffractometer	4851 independent reflections
Radiation source: fine-focus sealed tube	2145 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.057
phi and ω scans	θ_max = 25.0°, θ_min = 2.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→12
T_min = 0.937, T_max = 0.974	k = −27→25
13873 measured reflections	l = −13→11

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.122	H-atom parameters constrained
S = 0.83	w = 1/[σ²(F_o²) + (0.0486P)²] where P = (F_o² + 2F_c²)/3
4851 reflections	(Δ/σ)_max < 0.001
329 parameters	Δρ_max = 0.29 e Å⁻³
0 restraints	Δρ_min = −0.14 e Å⁻³

Crystal data top

C₃₀H₃₀N₄S₂	V = 2747.0 (4) Å³
M_r = 510.70	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 10.673 (1) Å	µ = 0.22 mm⁻¹
b = 22.906 (2) Å	T = 298 K
c = 11.2939 (11) Å	0.30 × 0.26 × 0.12 mm
β = 95.784 (1)°

Data collection top

Bruker SMART APEX CCD area-etector diffractometer	4851 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2145 reflections with I > 2σ(I)
T_min = 0.937, T_max = 0.974	R_int = 0.057
13873 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.051	0 restraints
wR(F²) = 0.122	H-atom parameters constrained
S = 0.83	Δρ_max = 0.29 e Å⁻³
4851 reflections	Δρ_min = −0.14 e Å⁻³
329 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.

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.

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

	x	y	z	U_iso*/U_eq
S1	0.19747 (8)	0.14806 (4)	0.72993 (7)	0.0713 (3)
S2	0.11991 (8)	0.22645 (4)	0.67335 (8)	0.0755 (3)
N1	−0.1215 (2)	0.28105 (12)	0.6062 (2)	0.0628 (7)
N2	0.3431 (2)	0.04770 (12)	0.7508 (2)	0.0705 (8)
N3	−0.3191 (3)	0.51151 (12)	0.8653 (3)	0.0786 (8)
N4	0.1784 (4)	−0.16806 (15)	1.0685 (3)	0.0984 (10)
C1	0.0171 (3)	0.20663 (13)	0.5451 (3)	0.0584 (8)
C2	0.0478 (3)	0.16385 (15)	0.4662 (3)	0.0704 (10)
H2	0.1245	0.1445	0.4793	0.085*
C3	−0.0350 (4)	0.14966 (15)	0.3680 (3)	0.0805 (10)
H3	−0.0139	0.1209	0.3155	0.097*
C4	−0.1484 (4)	0.17819 (16)	0.3485 (3)	0.0841 (11)
H4	−0.2047	0.1683	0.2834	0.101*
C5	−0.1786 (3)	0.22166 (15)	0.4258 (3)	0.0745 (10)
H5	−0.2556	0.2408	0.4122	0.089*
C6	−0.0955 (3)	0.23708 (14)	0.5236 (3)	0.0582 (8)
C7	−0.1777 (3)	0.32766 (15)	0.5692 (3)	0.0660 (9)
H7	−0.1983	0.3318	0.4877	0.079*
C8	−0.2120 (3)	0.37512 (14)	0.6467 (3)	0.0612 (9)
C9	−0.1778 (3)	0.37524 (14)	0.7692 (3)	0.0673 (9)
H9	−0.1314	0.3441	0.8036	0.081*
C10	−0.2107 (3)	0.42006 (15)	0.8401 (3)	0.0700 (9)
H10	−0.1851	0.4189	0.9213	0.084*
C11	−0.2818 (3)	0.46755 (14)	0.7935 (3)	0.0631 (9)
C12	−0.3114 (3)	0.46861 (14)	0.6697 (3)	0.0716 (10)
H12	−0.3553	0.5002	0.6344	0.086*
C13	−0.2766 (3)	0.42355 (15)	0.5998 (3)	0.0723 (10)
H13	−0.2971	0.4257	0.5179	0.087*
C14	−0.3916 (3)	0.56013 (16)	0.8147 (3)	0.1046 (13)
H14A	−0.3512	0.5762	0.7498	0.157*
H14B	−0.3972	0.5895	0.8745	0.157*
H14C	−0.4746	0.5471	0.7862	0.157*
C15	−0.3011 (4)	0.50616 (15)	0.9928 (3)	0.1034 (13)
H15A	−0.3390	0.4706	1.0165	0.155*
H15B	−0.3396	0.5388	1.0284	0.155*
H15C	−0.2126	0.5056	1.0187	0.155*
C16	0.3436 (3)	0.14305 (15)	0.6678 (3)	0.0619 (9)
C17	0.3972 (4)	0.18706 (15)	0.6046 (3)	0.0798 (10)
H17	0.3565	0.2228	0.5932	0.096*
C18	0.5101 (4)	0.17773 (18)	0.5590 (4)	0.0983 (13)
H18	0.5459	0.2073	0.5171	0.118*
C19	0.5702 (4)	0.1251 (2)	0.5750 (4)	0.1061 (14)
H19	0.6458	0.1188	0.5425	0.127*
C20	0.5192 (4)	0.08124 (17)	0.6390 (3)	0.0945 (12)
H20	0.5609	0.0457	0.6493	0.113*
C21	0.4060 (3)	0.08967 (15)	0.6882 (3)	0.0673 (9)
C22	0.4045 (3)	0.00799 (16)	0.8111 (3)	0.0750 (10)
H22	0.4919	0.0084	0.8145	0.090*
C23	0.3452 (3)	−0.03744 (15)	0.8743 (3)	0.0657 (9)
C24	0.2152 (3)	−0.04379 (15)	0.8688 (3)	0.0710 (10)
H24	0.1641	−0.0184	0.8214	0.085*
C25	0.1604 (3)	−0.08633 (16)	0.9311 (3)	0.0768 (10)
H25	0.0731	−0.0894	0.9241	0.092*
C26	0.2329 (4)	−0.12559 (16)	1.0054 (3)	0.0764 (10)
C27	0.3634 (4)	−0.11984 (16)	1.0115 (3)	0.0863 (11)
H27	0.4150	−0.1450	1.0591	0.104*
C28	0.4159 (3)	−0.07660 (16)	0.9467 (3)	0.0872 (11)
H28	0.5032	−0.0737	0.9519	0.105*
C29	0.0443 (5)	−0.17245 (17)	1.0621 (4)	0.1289 (17)
H29A	0.0103	−0.1368	1.0903	0.193*
H29B	0.0216	−0.2044	1.1107	0.193*
H29C	0.0109	−0.1791	0.9811	0.193*
C30	0.2540 (4)	−0.20578 (17)	1.1510 (3)	0.1166 (15)
H30A	0.3060	−0.2304	1.1075	0.175*
H30B	0.1996	−0.2296	1.1935	0.175*
H30C	0.3063	−0.1823	1.2064	0.175*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0717 (6)	0.0764 (7)	0.0644 (6)	0.0111 (5)	−0.0005 (5)	0.0060 (5)
S2	0.0801 (6)	0.0720 (6)	0.0704 (6)	0.0154 (5)	−0.0128 (5)	−0.0120 (5)
N1	0.0643 (18)	0.0658 (19)	0.0583 (17)	0.0104 (15)	0.0060 (14)	0.0049 (15)
N2	0.0727 (19)	0.064 (2)	0.073 (2)	0.0052 (16)	0.0010 (16)	0.0112 (16)
N3	0.096 (2)	0.060 (2)	0.081 (2)	0.0147 (17)	0.0124 (18)	0.0007 (17)
N4	0.114 (3)	0.083 (3)	0.105 (3)	−0.015 (2)	0.041 (2)	0.003 (2)
C1	0.063 (2)	0.059 (2)	0.053 (2)	0.0074 (17)	0.0034 (17)	0.0004 (17)
C2	0.073 (2)	0.073 (3)	0.064 (2)	0.0103 (19)	0.001 (2)	−0.0028 (19)
C3	0.100 (3)	0.075 (3)	0.064 (2)	0.015 (2)	−0.003 (2)	−0.0136 (19)
C4	0.096 (3)	0.085 (3)	0.066 (3)	0.011 (2)	−0.020 (2)	−0.012 (2)
C5	0.069 (2)	0.078 (3)	0.073 (2)	0.0173 (19)	−0.008 (2)	0.001 (2)
C6	0.064 (2)	0.062 (2)	0.048 (2)	0.0032 (18)	0.0043 (18)	0.0001 (17)
C7	0.065 (2)	0.075 (3)	0.057 (2)	0.0060 (19)	0.0044 (18)	0.0046 (19)
C8	0.062 (2)	0.060 (2)	0.062 (2)	0.0096 (17)	0.0117 (18)	0.0079 (18)
C9	0.082 (2)	0.060 (2)	0.061 (2)	0.0090 (18)	0.009 (2)	0.0105 (19)
C10	0.087 (2)	0.067 (3)	0.057 (2)	0.006 (2)	0.0074 (19)	0.0074 (19)
C11	0.058 (2)	0.056 (2)	0.077 (3)	0.0023 (17)	0.012 (2)	0.004 (2)
C12	0.076 (2)	0.059 (2)	0.079 (3)	0.0150 (18)	0.000 (2)	0.010 (2)
C13	0.078 (2)	0.071 (3)	0.066 (2)	0.015 (2)	−0.0003 (19)	0.008 (2)
C14	0.106 (3)	0.081 (3)	0.124 (3)	0.030 (2)	0.002 (3)	−0.010 (3)
C15	0.149 (4)	0.072 (3)	0.095 (3)	0.012 (2)	0.038 (3)	−0.002 (2)
C16	0.061 (2)	0.064 (2)	0.059 (2)	0.0001 (19)	−0.0057 (17)	0.0063 (17)
C17	0.080 (3)	0.067 (3)	0.092 (3)	0.003 (2)	0.003 (2)	0.010 (2)
C18	0.079 (3)	0.090 (3)	0.128 (4)	0.003 (2)	0.021 (3)	0.037 (3)
C19	0.074 (3)	0.116 (4)	0.133 (4)	0.012 (3)	0.029 (3)	0.034 (3)
C20	0.081 (3)	0.089 (3)	0.116 (3)	0.019 (2)	0.021 (3)	0.029 (2)
C21	0.061 (2)	0.070 (3)	0.071 (2)	0.006 (2)	0.0053 (19)	0.0096 (19)
C22	0.066 (2)	0.075 (3)	0.084 (3)	0.005 (2)	0.006 (2)	0.006 (2)
C23	0.059 (2)	0.065 (3)	0.073 (2)	0.0095 (19)	0.008 (2)	0.0055 (18)
C24	0.072 (3)	0.067 (3)	0.072 (2)	0.009 (2)	0.001 (2)	−0.0030 (19)
C25	0.073 (3)	0.077 (3)	0.081 (3)	−0.006 (2)	0.010 (2)	−0.009 (2)
C26	0.095 (3)	0.062 (3)	0.077 (3)	−0.002 (2)	0.028 (2)	−0.006 (2)
C27	0.080 (3)	0.078 (3)	0.103 (3)	0.020 (2)	0.020 (2)	0.029 (2)
C28	0.067 (2)	0.085 (3)	0.112 (3)	0.018 (2)	0.020 (2)	0.023 (2)
C29	0.145 (5)	0.101 (4)	0.151 (4)	−0.040 (3)	0.070 (4)	−0.015 (3)
C30	0.175 (5)	0.084 (3)	0.095 (3)	−0.006 (3)	0.034 (3)	0.015 (3)

Geometric parameters (Å, º) top

S1—C16	1.777 (3)	C14—H14A	0.9600
S1—S2	2.0521 (12)	C14—H14B	0.9600
S2—C1	1.786 (3)	C14—H14C	0.9600
N1—C7	1.274 (3)	C15—H15A	0.9600
N1—C6	1.419 (4)	C15—H15B	0.9600
N2—C22	1.277 (4)	C15—H15C	0.9600
N2—C21	1.404 (4)	C16—C17	1.391 (4)
N3—C11	1.376 (4)	C16—C21	1.400 (4)
N3—C15	1.440 (4)	C17—C18	1.375 (4)
N3—C14	1.441 (4)	C17—H17	0.9300
N4—C26	1.370 (4)	C18—C19	1.370 (5)
N4—C29	1.429 (5)	C18—H18	0.9300
N4—C30	1.454 (4)	C19—C20	1.380 (4)
C1—C2	1.386 (4)	C19—H19	0.9300
C1—C6	1.389 (4)	C20—C21	1.393 (4)
C2—C3	1.385 (4)	C20—H20	0.9300
C2—H2	0.9300	C22—C23	1.444 (4)
C3—C4	1.373 (4)	C22—H22	0.9300
C3—H3	0.9300	C23—C28	1.385 (4)
C4—C5	1.384 (4)	C23—C24	1.390 (4)
C4—H4	0.9300	C24—C25	1.367 (4)
C5—C6	1.391 (4)	C24—H24	0.9300
C5—H5	0.9300	C25—C26	1.408 (4)
C7—C8	1.465 (4)	C25—H25	0.9300
C7—H7	0.9300	C26—C27	1.393 (4)
C8—C13	1.383 (4)	C27—C28	1.384 (4)
C8—C9	1.395 (4)	C27—H27	0.9300
C9—C10	1.370 (4)	C28—H28	0.9300
C9—H9	0.9300	C29—H29A	0.9600
C10—C11	1.399 (4)	C29—H29B	0.9600
C10—H10	0.9300	C29—H29C	0.9600
C11—C12	1.403 (4)	C30—H30A	0.9600
C12—C13	1.373 (4)	C30—H30B	0.9600
C12—H12	0.9300	C30—H30C	0.9600
C13—H13	0.9300

C16—S1—S2	106.03 (12)	N3—C15—H15B	109.5
C1—S2—S1	103.05 (11)	H15A—C15—H15B	109.5
C7—N1—C6	119.7 (3)	N3—C15—H15C	109.5
C22—N2—C21	120.7 (3)	H15A—C15—H15C	109.5
C11—N3—C15	120.7 (3)	H15B—C15—H15C	109.5
C11—N3—C14	120.5 (3)	C17—C16—C21	120.2 (3)
C15—N3—C14	118.3 (3)	C17—C16—S1	125.3 (3)
C26—N4—C29	120.0 (4)	C21—C16—S1	114.4 (3)
C26—N4—C30	121.2 (4)	C18—C17—C16	120.1 (3)
C29—N4—C30	118.6 (3)	C18—C17—H17	120.0
C2—C1—C6	120.0 (3)	C16—C17—H17	120.0
C2—C1—S2	122.4 (3)	C19—C18—C17	120.3 (4)
C6—C1—S2	117.6 (2)	C19—C18—H18	119.9
C3—C2—C1	120.5 (3)	C17—C18—H18	119.9
C3—C2—H2	119.8	C18—C19—C20	120.3 (4)
C1—C2—H2	119.8	C18—C19—H19	119.8
C4—C3—C2	119.8 (3)	C20—C19—H19	119.8
C4—C3—H3	120.1	C19—C20—C21	120.8 (4)
C2—C3—H3	120.1	C19—C20—H20	119.6
C3—C4—C5	119.9 (3)	C21—C20—H20	119.6
C3—C4—H4	120.0	C20—C21—C16	118.2 (3)
C5—C4—H4	120.0	C20—C21—N2	125.8 (3)
C4—C5—C6	120.8 (3)	C16—C21—N2	115.9 (3)
C4—C5—H5	119.6	N2—C22—C23	123.4 (3)
C6—C5—H5	119.6	N2—C22—H22	118.3
C1—C6—C5	118.8 (3)	C23—C22—H22	118.3
C1—C6—N1	117.7 (3)	C28—C23—C24	116.2 (3)
C5—C6—N1	123.4 (3)	C28—C23—C22	121.2 (3)
N1—C7—C8	124.3 (3)	C24—C23—C22	122.6 (3)
N1—C7—H7	117.9	C25—C24—C23	121.9 (3)
C8—C7—H7	117.9	C25—C24—H24	119.1
C13—C8—C9	116.7 (3)	C23—C24—H24	119.1
C13—C8—C7	120.7 (3)	C24—C25—C26	121.6 (3)
C9—C8—C7	122.5 (3)	C24—C25—H25	119.2
C10—C9—C8	121.6 (3)	C26—C25—H25	119.2
C10—C9—H9	119.2	N4—C26—C27	121.1 (4)
C8—C9—H9	119.2	N4—C26—C25	121.8 (4)
C9—C10—C11	121.6 (3)	C27—C26—C25	117.1 (3)
C9—C10—H10	119.2	C28—C27—C26	119.9 (4)
C11—C10—H10	119.2	C28—C27—H27	120.1
N3—C11—C10	121.7 (3)	C26—C27—H27	120.1
N3—C11—C12	121.7 (3)	C27—C28—C23	123.3 (3)
C10—C11—C12	116.6 (3)	C27—C28—H28	118.3
C13—C12—C11	120.9 (3)	C23—C28—H28	118.3
C13—C12—H12	119.6	N4—C29—H29A	109.5
C11—C12—H12	119.6	N4—C29—H29B	109.5
C12—C13—C8	122.4 (3)	H29A—C29—H29B	109.5
C12—C13—H13	118.8	N4—C29—H29C	109.5
C8—C13—H13	118.8	H29A—C29—H29C	109.5
N3—C14—H14A	109.5	H29B—C29—H29C	109.5
N3—C14—H14B	109.5	N4—C30—H30A	109.5
H14A—C14—H14B	109.5	N4—C30—H30B	109.5
N3—C14—H14C	109.5	H30A—C30—H30B	109.5
H14A—C14—H14C	109.5	N4—C30—H30C	109.5
H14B—C14—H14C	109.5	H30A—C30—H30C	109.5
N3—C15—H15A	109.5	H30B—C30—H30C	109.5

Experimental details

Crystal data
Chemical formula	C₃₀H₃₀N₄S₂
M_r	510.70
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	298
a, b, c (Å)	10.673 (1), 22.906 (2), 11.2939 (11)
β (°)	95.784 (1)
V (Å³)	2747.0 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.22
Crystal size (mm)	0.30 × 0.26 × 0.12

Data collection
Diffractometer	Bruker SMART APEX CCD area-etector
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.937, 0.974
No. of measured, independent and observed [I > 2σ(I)] reflections	13873, 4851, 2145
R_int	0.057
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.051, 0.122, 0.83
No. of reflections	4851
No. of parameters	329
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.29, −0.14

Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Acknowledgements

This project was supported by the Foundation of Liaocheng University (grant No. X10007) and the Graduate Education Innovation Program of Liaocheng University (grant No. LCUYZ11001).

References

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