2-Amino-5-methyl-6-methyl-sulfanyl-4-phenyl-benzene-1,3-dicarbonitrile.

The dihedral angle between the planes of the two aromatic rings of the title compound, C(16)H(13)N(3)S, is 56.7 (3)°. The crystal packing is stabilized by inter-molecular N-H⋯N hydrogen bonds, which link the mol-ecules into chains along [11[Formula: see text]].

Related literature

For medicinal and biological properities of aromatic o-amino dinitrile derivatives, see Singh et al. (2009 ▶); Goel & Singh (2005 ▶); Pratap & Ramb (2008 ▶). For a related structure, see Singh et al. (2006 ▶).

Experimental

Crystal data

C16H13N3S

M = 279.35

Triclinic,

a = 8.959 (2) Å

b = 9.123 (2) Å

c = 10.1240 (19) Å

α = 65.843 (7)°

β = 68.362 (8)°

γ = 88.754 (10)°

V = 693.6 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.23 mm−1

T = 153 K

0.50 × 0.18 × 0.07 mm

Data collection

Rigaku AFC10/Saturn724+ diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2008 ▶) T min = 0.896, T max = 0.985

7468 measured reflections

3601 independent reflections

2825 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.092

S = 1.00

3601 reflections

191 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.42 e Å−3

Δρmin = −0.22 e Å−3

Data collection: CrystalClear (Rigaku, 2008 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811055243/fy2026sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811055243/fy2026Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811055243/fy2026Isup3.cml

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

C16H13N3S	F(000) = 292
Mr = 279.35	Dx = 1.338 Mg m−3
Triclinic, P1	Melting point: 502 K
a = 8.959 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.123 (2) Å	Cell parameters from 2338 reflections
c = 10.1240 (19) Å	θ = 2.4–29.1°
α = 65.843 (7)°	µ = 0.23 mm−1
β = 68.362 (8)°	T = 153 K
γ = 88.754 (10)°	Chunk, colourless
V = 693.6 (3) Å3	0.50 × 0.18 × 0.07 mm
Z = 2

Rigaku AFC10/Saturn724+ diffractometer	3601 independent reflections
Radiation source: rotating anode	2825 reflections with I > 2σ(I)
graphite	Rint = 0.023
Detector resolution: 28.5714 pixels mm-1	θmax = 29.1°, θmin = 2.5°
φ and ω scans	h = −12→12
Absorption correction: multi-scan (CrystalClear; Rigaku, 2008)	k = −12→11
Tmin = 0.896, Tmax = 0.985	l = −12→13
7468 measured reflections

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.092	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ2(Fo2) + (0.0451P)2 + 0.060P] where P = (Fo2 + 2Fc2)/3
3601 reflections	(Δ/σ)max = 0.001
191 parameters	Δρmax = 0.42 e Å−3
0 restraints	Δρmin = −0.22 e Å−3

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	Uiso*/Ueq
S1	0.29042 (4)	−0.05634 (4)	0.85224 (4)	0.02678 (11)
N1	0.60522 (14)	0.56001 (14)	0.06550 (13)	0.0283 (3)
N2	0.29233 (14)	0.23632 (15)	0.29819 (14)	0.0249 (3)
N3	0.01854 (14)	−0.04570 (15)	0.65642 (14)	0.0303 (3)
C1	0.51849 (14)	0.31928 (15)	0.34085 (14)	0.0172 (3)
C2	0.37070 (14)	0.21875 (15)	0.39343 (14)	0.0177 (3)
C3	0.30635 (14)	0.10607 (15)	0.55414 (14)	0.0181 (3)
C4	0.38693 (15)	0.09060 (15)	0.65317 (14)	0.0189 (3)
C5	0.53818 (15)	0.18480 (15)	0.59641 (14)	0.0192 (3)
C6	0.60130 (14)	0.30197 (15)	0.43875 (14)	0.0174 (2)
C7	0.75896 (14)	0.41104 (15)	0.36946 (14)	0.0182 (3)
C8	0.78192 (16)	0.51184 (16)	0.43512 (16)	0.0235 (3)
H8	0.6965	0.5123	0.5249	0.028*
C9	0.92966 (17)	0.61171 (16)	0.36943 (17)	0.0272 (3)
H9	0.9448	0.6805	0.4144	0.033*
C10	1.05420 (16)	0.61142 (17)	0.23934 (17)	0.0296 (3)
H10	1.1552	0.6794	0.1954	0.035*
C11	1.03249 (16)	0.51254 (18)	0.17277 (16)	0.0289 (3)
H11	1.1184	0.5127	0.0829	0.035*
C12	0.88490 (15)	0.41272 (16)	0.23729 (15)	0.0225 (3)
H12	0.8700	0.3453	0.1909	0.027*
C13	0.57249 (14)	0.45223 (15)	0.18627 (14)	0.0194 (3)
C14	0.14689 (15)	0.01656 (15)	0.61603 (14)	0.0213 (3)
C15	0.63082 (17)	0.15707 (17)	0.70024 (16)	0.0271 (3)
H15A	0.7477	0.1832	0.6354	0.033*
H15B	0.6043	0.0430	0.7777	0.033*
H15C	0.6006	0.2270	0.7551	0.033*
C16	0.2306 (2)	0.0743 (2)	0.95114 (17)	0.0398 (4)
H16A	0.3277	0.1310	0.9427	0.048*
H16B	0.1618	0.0086	1.0625	0.048*
H16C	0.1699	0.1541	0.9019	0.048*
H2A	0.205 (2)	0.169 (2)	0.330 (2)	0.039 (5)*
H2B	0.333 (2)	0.301 (2)	0.201 (2)	0.035 (5)*

	U11	U22	U33	U12	U13	U23
S1	0.03045 (19)	0.02449 (19)	0.01632 (16)	−0.00576 (13)	−0.00669 (13)	−0.00220 (13)
N1	0.0253 (6)	0.0297 (7)	0.0223 (6)	−0.0050 (5)	−0.0090 (5)	−0.0039 (5)
N2	0.0217 (5)	0.0272 (6)	0.0187 (6)	−0.0074 (5)	−0.0089 (5)	−0.0020 (5)
N3	0.0267 (6)	0.0311 (7)	0.0247 (6)	−0.0071 (5)	−0.0085 (5)	−0.0050 (5)
C1	0.0158 (5)	0.0164 (6)	0.0158 (6)	−0.0001 (4)	−0.0033 (4)	−0.0061 (5)
C2	0.0173 (6)	0.0166 (6)	0.0179 (6)	0.0012 (5)	−0.0058 (5)	−0.0073 (5)
C3	0.0167 (5)	0.0167 (6)	0.0176 (6)	−0.0012 (4)	−0.0043 (5)	−0.0065 (5)
C4	0.0204 (6)	0.0170 (6)	0.0148 (6)	−0.0006 (5)	−0.0050 (5)	−0.0044 (5)
C5	0.0188 (6)	0.0185 (6)	0.0196 (6)	0.0016 (5)	−0.0076 (5)	−0.0076 (5)
C6	0.0152 (5)	0.0169 (6)	0.0190 (6)	0.0014 (4)	−0.0044 (5)	−0.0087 (5)
C7	0.0153 (5)	0.0170 (6)	0.0199 (6)	0.0018 (4)	−0.0075 (5)	−0.0053 (5)
C8	0.0205 (6)	0.0237 (7)	0.0272 (7)	0.0036 (5)	−0.0086 (5)	−0.0126 (6)
C9	0.0278 (7)	0.0197 (7)	0.0382 (8)	0.0016 (5)	−0.0191 (6)	−0.0107 (6)
C10	0.0211 (6)	0.0280 (8)	0.0297 (7)	−0.0061 (5)	−0.0133 (6)	0.0002 (6)
C11	0.0172 (6)	0.0395 (8)	0.0192 (6)	−0.0005 (6)	−0.0036 (5)	−0.0055 (6)
C12	0.0201 (6)	0.0262 (7)	0.0192 (6)	0.0025 (5)	−0.0073 (5)	−0.0084 (5)
C13	0.0156 (5)	0.0222 (7)	0.0205 (6)	−0.0007 (5)	−0.0068 (5)	−0.0094 (5)
C14	0.0232 (6)	0.0193 (7)	0.0172 (6)	−0.0013 (5)	−0.0070 (5)	−0.0046 (5)
C15	0.0262 (7)	0.0279 (8)	0.0243 (7)	−0.0018 (6)	−0.0132 (6)	−0.0054 (6)
C16	0.0481 (10)	0.0412 (10)	0.0213 (7)	0.0046 (7)	−0.0064 (7)	−0.0119 (7)

S1—C4	1.7778 (13)	C7—C12	1.3908 (18)
S1—C16	1.8064 (16)	C7—C8	1.3926 (18)
N1—C13	1.1453 (16)	C8—C9	1.3898 (17)
N2—C2	1.3477 (16)	C8—H8	0.9500
N2—H2A	0.872 (17)	C9—C10	1.378 (2)
N2—H2B	0.849 (17)	C9—H9	0.9500
N3—C14	1.1417 (16)	C10—C11	1.381 (2)
C1—C6	1.4025 (17)	C10—H10	0.9500
C1—C2	1.4181 (15)	C11—C12	1.3904 (17)
C1—C13	1.4380 (16)	C11—H11	0.9500
C2—C3	1.4147 (16)	C12—H12	0.9500
C3—C4	1.3999 (17)	C15—H15A	0.9800
C3—C14	1.4395 (16)	C15—H15B	0.9800
C4—C5	1.4062 (16)	C15—H15C	0.9800
C5—C6	1.4051 (17)	C16—H16A	0.9800
C5—C15	1.5082 (18)	C16—H16B	0.9800
C6—C7	1.4955 (16)	C16—H16C	0.9800
C4—S1—C16	100.64 (7)	C7—C8—H8	120.0
C2—N2—H2A	120.8 (11)	C10—C9—C8	120.28 (13)
C2—N2—H2B	122.4 (11)	C10—C9—H9	119.9
H2A—N2—H2B	116.0 (15)	C8—C9—H9	119.9
C6—C1—C2	122.37 (11)	C9—C10—C11	120.13 (12)
C6—C1—C13	120.51 (10)	C9—C10—H10	119.9
C2—C1—C13	116.82 (11)	C11—C10—H10	119.9
N2—C2—C3	122.31 (11)	C10—C11—C12	120.00 (13)
N2—C2—C1	121.85 (11)	C10—C11—H11	120.0
C3—C2—C1	115.74 (11)	C12—C11—H11	120.0
C4—C3—C2	122.01 (11)	C11—C12—C7	120.30 (13)
C4—C3—C14	120.70 (11)	C11—C12—H12	119.8
C2—C3—C14	117.08 (11)	C7—C12—H12	119.8
C3—C4—C5	121.35 (11)	N1—C13—C1	175.53 (13)
C3—C4—S1	116.68 (9)	N3—C14—C3	175.06 (14)
C5—C4—S1	121.96 (10)	C5—C15—H15A	109.5
C6—C5—C4	117.56 (11)	C5—C15—H15B	109.5
C6—C5—C15	121.49 (11)	H15A—C15—H15B	109.5
C4—C5—C15	120.93 (11)	C5—C15—H15C	109.5
C1—C6—C5	120.81 (10)	H15A—C15—H15C	109.5
C1—C6—C7	117.86 (11)	H15B—C15—H15C	109.5
C5—C6—C7	121.33 (11)	S1—C16—H16A	109.5
C12—C7—C8	119.20 (11)	S1—C16—H16B	109.5
C12—C7—C6	119.83 (11)	H16A—C16—H16B	109.5
C8—C7—C6	120.97 (11)	S1—C16—H16C	109.5
C9—C8—C7	120.08 (13)	H16A—C16—H16C	109.5
C9—C8—H8	120.0	H16B—C16—H16C	109.5
C6—C1—C2—N2	−179.89 (13)	C13—C1—C6—C5	172.08 (12)
C13—C1—C2—N2	6.36 (19)	C2—C1—C6—C7	178.04 (12)
C6—C1—C2—C3	3.76 (19)	C13—C1—C6—C7	−8.43 (18)
C13—C1—C2—C3	−169.99 (11)	C4—C5—C6—C1	−2.33 (19)
N2—C2—C3—C4	−178.76 (13)	C15—C5—C6—C1	175.93 (12)
C1—C2—C3—C4	−2.42 (19)	C4—C5—C6—C7	178.20 (12)
N2—C2—C3—C14	−3.88 (19)	C15—C5—C6—C7	−3.54 (19)
C1—C2—C3—C14	172.45 (12)	C1—C6—C7—C12	−57.24 (17)
C2—C3—C4—C5	−1.3 (2)	C5—C6—C7—C12	122.25 (14)
C14—C3—C4—C5	−175.95 (12)	C1—C6—C7—C8	122.61 (14)
C2—C3—C4—S1	179.95 (10)	C5—C6—C7—C8	−57.90 (17)
C14—C3—C4—S1	5.26 (17)	C12—C7—C8—C9	−0.5 (2)
C16—S1—C4—C3	−109.99 (12)	C6—C7—C8—C9	179.67 (13)
C16—S1—C4—C5	71.23 (13)	C7—C8—C9—C10	−0.1 (2)
C3—C4—C5—C6	3.7 (2)	C8—C9—C10—C11	0.4 (2)
S1—C4—C5—C6	−177.62 (10)	C9—C10—C11—C12	−0.2 (2)
C3—C4—C5—C15	−174.62 (13)	C10—C11—C12—C7	−0.4 (2)
S1—C4—C5—C15	4.11 (18)	C8—C7—C12—C11	0.7 (2)
C2—C1—C6—C5	−1.4 (2)	C6—C7—C12—C11	−179.41 (12)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2B···N1i	0.849 (17)	2.305 (17)	3.1360 (17)	166.2 (14)
N2—H2A···N3ii	0.872 (17)	2.253 (18)	3.0993 (17)	163.4 (15)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2B⋯N1i	0.849 (17)	2.305 (17)	3.1360 (17)	166.2 (14)
N2—H2A⋯N3ii	0.872 (17)	2.253 (18)	3.0993 (17)	163.4 (15)

Symmetry codes: (i) ; (ii) .