3-Amino-1-(thio­phen-2-yl)-9,10-dihydro­phenanthrene-2,4-dicarbonitrile

Al-Youbi, A.O.; Asiri, A.M.; Faidallah, H.M.; Ng, S.W.; Tiekink, E.R.T.

doi:10.1107/S1600536812010033

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 68| Part 4| April 2012| Pages o1027-o1028

doi:10.1107/S1600536812010033

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3-Amino-1-(thiophen-2-yl)-9,10-dihydrophenanthrene-2,4-dicarbonitrile

Abdulrahman O. Al-Youbi,^a,^b ‡ Abdullah M. Asiri,^a,^b Hassan M. Faidallah,^a Seik Weng Ng ^c,^a and Edward R. T. Tiekink ^c ^*

^aChemistry Department, Faculty of Science, King Abdulaziz University, PO Box 80203, Jeddah, Saudi Arabia, ^bThe Center of Excellence for Advanced Materials Research, King Abdulaziz University, Jeddah, PO Box 80203, Saudi Arabia, and ^cDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: edward.tiekink@gmail.com

(Received 5 March 2012; accepted 7 March 2012; online 10 March 2012)

In the title compound, C₂₀H₁₃N₃S, the partially saturated ring adopts a twisted half-boat conformation with the methylene C atom closest to the aminobenzene ring lying 0.690 (6) Å out of the plane defined by the five remaining atoms. The dihydrophenanthrene residue has a folded conformation [dihedral angle between the outer benzene rings = 26.27 (18)°]. The thiophen-2-yl ring forms a dihedral angle of 63.76 (19)° with the benzene ring to which it is attached. In the crystal, inversion dimers linked by pairs of N—H⋯N hydrogen bonds generate R₂²(12) loops. The dimers are linked into layers in the bc plane by weak C—H⋯π interactions. The thiophen-2-yl ring is disordered over two essentially coplanar but opposite orientations in a 0.918 (4):0.082 (4) ratio.

Related literature

For background to the biological activity of related dicarbonitrile compounds, see: Aly et al. (1991 ); Rostom et al. (2011 ). For related structures, see: Asiri et al. (2011a ,b ).

Experimental

Crystal data

C₂₀H₁₃N₃S
M_r = 327.39
Monoclinic, P 2₁ /c
a = 9.7882 (10) Å
b = 7.1199 (7) Å
c = 22.746 (3) Å
β = 93.171 (11)°
V = 1582.8 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.21 mm⁻¹
T = 100 K
0.30 × 0.06 × 0.03 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ) T_min = 0.940, T_max = 0.994
5527 measured reflections
2805 independent reflections
1778 reflections with I > 2σ(I)
R_int = 0.056

Refinement

R[F² > 2σ(F²)] = 0.066
wR(F²) = 0.164
S = 1.03
2805 reflections
236 parameters
56 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.67 e Å⁻³
Δρ_min = −0.55 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C4–C9 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H1⋯N3ⁱ	0.88 (3)	2.18 (3)	3.016 (5)	160 (3)
C6—H6⋯Cg1ⁱⁱ	0.95	2.85	3.660 (5)	144
Symmetry codes: (i) -x+1, -y, -z+1; (ii) $[-x+1, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Data collection: CrysAlis PRO (Agilent, 2011); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ) and DIAMOND (Brandenburg, 2006 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812010033/hb6670sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812010033/hb6670Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812010033/hb6670Isup3.cml

checkCIF report

Comment top

The crystallographic investigation of the title compound, (I), was motivated by reports of the biological activity of related compounds (Aly et al., 1991; Rostom et al., 2011) and allied crystal structure investigations (Asiri et al., 2011a; Asiri et al., 2011b).

In (I), Fig. 1, the partially saturated ring adopts a twisted half boat conformation with the C2 atom lying 0.690 (6) Å out of the plane defined by the five remaining atoms [r.m.s. deviation = 0.1032 Å; maximum deviations = 0.076 (3) Å for the C9 atom and -0.160 (3) Å for the C10 atom]. The dihedral angle between the adjacent benzene rings = 26.27 (18)° indicating a fold in the molecule. The thiophen-2-yl ring forms a dihedral angle of 63.76 (19)° with the benzene to which it is attached.

In the crystal packing, centrosymmetric aggregates are formed via N—H···N hydrogen bonds leading to 12-membered {···HNC₃N}₂ synthons, Table 1. These are linked into layers in the bc plane by C—H···π interactions, Fig. 2 and Table 1. These stack along the a axis with no specific interactions between them.

Related literature top

For background to the biological activity of related dicarbonitrile compounds, see: Aly et al. (1991); Rostom et al. (2011). For related structures, see: Asiri et al. (2011a,b).

Experimental top

A mixture of thiophene-2-cabaldehyde (1.1 g, 10 mmol), 1-tetralone (1.46 g, 10 mmol), malononitrile (0.66 g, 10 mmol) and ammonium acetate (6.2 g, 80 mmol) in absolute ethanol (50 ml) was refluxed for 6 h. The reaction mixture was allowed to cool, and the formed precipitate was filtered, washed with water, dried and recrystallized from ethanol as orange prisms. Yield: 69%. M.pt: 451–453 K.

Structure description top

For background to the biological activity of related dicarbonitrile compounds, see: Aly et al. (1991); Rostom et al. (2011). For related structures, see: Asiri et al. (2011a,b).

Computing details top

Data collection: CrysAlis PRO (Agilent, 2011); cell refinement: CrysAlis PRO (Agilent, 2011); data reduction: CrysAlis PRO (Agilent, 2011); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

	Fig. 1. The molecular structure of (I) showing displacement ellipsoids at the 50% probability level.
	Fig. 2. A view of the supramolecular layer in the bc plane in (I). The C—H···O and C—H···π interactions are shown as orange and purple dashed lines, respectively.
	Fig. 3. A view in projection down the b axis of the unit-cell contents of (I) showing the stacking of layers. The C—H···O and C—H···π interactions are shown as orange and purple dashed lines, respectively. One layer is highlighted in space-filling mode.

3-Amino-1-(thiophen-2-yl)-9,10-dihydrophenanthrene-2,4-dicarbonitrile top

Crystal data top

C₂₀H₁₃N₃S	F(000) = 680
M_r = 327.39	D_x = 1.374 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1132 reflections
a = 9.7882 (10) Å	θ = 2.7–25.0°
b = 7.1199 (7) Å	µ = 0.21 mm⁻¹
c = 22.746 (3) Å	T = 100 K
β = 93.171 (11)°	Prism, orange
V = 1582.8 (3) Å³	0.30 × 0.06 × 0.03 mm
Z = 4

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	2805 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	1778 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.056
Detector resolution: 10.4041 pixels mm^-1	θ_max = 25.1°, θ_min = 2.7°
ω scan	h = −9→11
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	k = −8→6
T_min = 0.940, T_max = 0.994	l = −19→27
5527 measured reflections

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)] = 0.066	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.164	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ²(F_o²) + (0.0559P)² + 1.2744P] where P = (F_o² + 2F_c²)/3
2805 reflections	(Δ/σ)_max = 0.001
236 parameters	Δρ_max = 0.67 e Å⁻³
56 restraints	Δρ_min = −0.55 e Å⁻³

Crystal data top

C₂₀H₁₃N₃S	V = 1582.8 (3) Å³
M_r = 327.39	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 9.7882 (10) Å	µ = 0.21 mm⁻¹
b = 7.1199 (7) Å	T = 100 K
c = 22.746 (3) Å	0.30 × 0.06 × 0.03 mm
β = 93.171 (11)°

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	2805 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	1778 reflections with I > 2σ(I)
T_min = 0.940, T_max = 0.994	R_int = 0.056
5527 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.066	56 restraints
wR(F²) = 0.164	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.67 e Å⁻³
2805 reflections	Δρ_min = −0.55 e Å⁻³
236 parameters

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
S1	0.98458 (11)	0.25812 (17)	0.64193 (6)	0.0331 (4)	0.918 (4)
S1'	0.976 (2)	0.275 (3)	0.5229 (7)	0.0358 (13)	0.082 (4)
N1	0.2456 (3)	0.6816 (5)	0.61810 (16)	0.0329 (9)
N2	0.3958 (3)	0.3401 (5)	0.54813 (14)	0.0213 (7)
H1	0.402 (4)	0.236 (3)	0.5276 (15)	0.026*
H2	0.3108 (16)	0.373 (5)	0.5535 (17)	0.026*
N3	0.6533 (3)	0.0358 (5)	0.51041 (15)	0.0255 (8)
C1	0.7477 (4)	0.6177 (5)	0.61652 (16)	0.0213 (9)
C2	0.8711 (4)	0.7249 (5)	0.64154 (18)	0.0262 (9)
H2A	0.8904	0.8322	0.6156	0.031*
H2B	0.9523	0.6418	0.6438	0.031*
C3	0.8422 (4)	0.7966 (6)	0.70321 (18)	0.0329 (11)
H3A	0.8278	0.6888	0.7297	0.039*
H3B	0.9215	0.8696	0.7196	0.039*
C4	0.7144 (4)	0.9209 (5)	0.69949 (19)	0.0295 (10)
C5	0.7052 (5)	1.0784 (6)	0.73318 (19)	0.0380 (11)
H5	0.7768	1.1082	0.7615	0.046*
C6	0.5919 (4)	1.1956 (6)	0.72634 (19)	0.0329 (11)
H6	0.5848	1.3024	0.7510	0.040*
C7	0.4905 (4)	1.1578 (5)	0.68423 (18)	0.0289 (10)
H7	0.4145	1.2402	0.6792	0.035*
C8	0.4980 (4)	0.9990 (5)	0.64865 (18)	0.0260 (10)
H8	0.4288	0.9752	0.6187	0.031*
C9	0.6089 (4)	0.8743 (5)	0.65742 (16)	0.0221 (9)
C10	0.6174 (4)	0.6957 (5)	0.62403 (16)	0.0201 (9)
C11	0.5006 (3)	0.5995 (5)	0.60216 (16)	0.0173 (8)
C12	0.5094 (4)	0.4290 (5)	0.57009 (16)	0.0184 (8)
C13	0.6410 (3)	0.3549 (5)	0.56377 (16)	0.0170 (8)
C14	0.7610 (3)	0.4495 (5)	0.58825 (16)	0.0202 (9)
C15	0.3602 (4)	0.6548 (5)	0.61278 (17)	0.0237 (9)
C16	0.6518 (3)	0.1773 (5)	0.53443 (16)	0.0193 (9)
C17	0.8889 (3)	0.3421 (4)	0.58171 (17)	0.0234 (9)
C18	0.9449 (5)	0.2974 (7)	0.5317 (2)	0.0358 (13)	0.918 (4)
H18	0.9073	0.3340	0.4940	0.043*	0.918 (4)
C18'	0.953 (2)	0.282 (3)	0.6333 (6)	0.0331 (4)	0.08
H18'	0.9194	0.3055	0.6710	0.040*	0.082 (4)
C19	1.0686 (4)	0.1878 (6)	0.5402 (2)	0.0325 (13)	0.918 (4)
H19	1.1203	0.1430	0.5089	0.039*	0.918 (4)
C19'	1.0749 (19)	0.179 (3)	0.6240 (13)	0.0361 (13)	0.082 (4)
H19'	1.1321	0.1274	0.6549	0.043*	0.082 (4)
C20	1.1022 (4)	0.1564 (6)	0.5979 (2)	0.0361 (13)	0.918 (4)
H20	1.1802	0.0875	0.6122	0.043*	0.918 (4)
C20'	1.1006 (14)	0.1645 (15)	0.5660 (15)	0.0325 (13)	0.08
H20'	1.1771	0.1011	0.5514	0.039*	0.082 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0230 (7)	0.0336 (7)	0.0420 (8)	0.0037 (5)	−0.0030 (5)	0.0073 (6)
S1'	0.021 (3)	0.045 (3)	0.043 (3)	0.005 (2)	0.015 (2)	−0.020 (2)
N1	0.025 (2)	0.035 (2)	0.038 (2)	0.0062 (16)	0.0029 (17)	0.0003 (17)
N2	0.0165 (16)	0.0228 (17)	0.0244 (19)	−0.0001 (15)	−0.0003 (14)	−0.0056 (15)
N3	0.0169 (17)	0.0238 (19)	0.036 (2)	0.0003 (14)	0.0039 (15)	−0.0071 (17)
C1	0.022 (2)	0.021 (2)	0.021 (2)	−0.0035 (17)	0.0023 (16)	0.0002 (17)
C2	0.024 (2)	0.023 (2)	0.032 (2)	−0.0028 (18)	0.0044 (18)	−0.0083 (19)
C3	0.032 (2)	0.035 (2)	0.031 (3)	−0.005 (2)	−0.0030 (19)	−0.010 (2)
C4	0.034 (2)	0.021 (2)	0.032 (3)	−0.0097 (19)	−0.0055 (19)	0.0035 (19)
C5	0.047 (3)	0.041 (3)	0.026 (3)	−0.004 (2)	0.012 (2)	−0.006 (2)
C6	0.047 (3)	0.027 (2)	0.026 (2)	−0.002 (2)	0.018 (2)	−0.007 (2)
C7	0.040 (2)	0.020 (2)	0.029 (2)	0.0020 (19)	0.016 (2)	0.0036 (19)
C8	0.033 (2)	0.022 (2)	0.023 (2)	−0.0007 (19)	0.0085 (18)	−0.0005 (18)
C9	0.030 (2)	0.0173 (19)	0.020 (2)	−0.0026 (18)	0.0090 (17)	0.0006 (17)
C10	0.023 (2)	0.019 (2)	0.018 (2)	−0.0003 (17)	0.0038 (16)	0.0037 (16)
C11	0.0177 (19)	0.0141 (18)	0.021 (2)	0.0009 (16)	0.0038 (16)	0.0016 (16)
C12	0.021 (2)	0.0190 (19)	0.015 (2)	0.0010 (17)	0.0041 (16)	0.0029 (16)
C13	0.0161 (19)	0.0154 (18)	0.020 (2)	0.0000 (16)	0.0063 (15)	0.0004 (16)
C14	0.020 (2)	0.020 (2)	0.021 (2)	−0.0004 (16)	0.0051 (16)	0.0016 (17)
C15	0.032 (2)	0.018 (2)	0.020 (2)	−0.0007 (18)	−0.0020 (18)	−0.0004 (17)
C16	0.0144 (19)	0.022 (2)	0.021 (2)	−0.0030 (16)	0.0006 (16)	0.0018 (18)
C17	0.0176 (19)	0.023 (2)	0.030 (2)	−0.0044 (17)	0.0021 (17)	−0.0049 (18)
C18	0.021 (3)	0.045 (3)	0.043 (3)	0.005 (2)	0.015 (2)	−0.020 (2)
C18'	0.0230 (7)	0.0336 (7)	0.0420 (8)	0.0037 (5)	−0.0030 (5)	0.0073 (6)
C19	0.011 (2)	0.033 (2)	0.053 (3)	0.0018 (19)	0.000 (2)	−0.021 (2)
C19'	0.018 (2)	0.027 (2)	0.064 (4)	0.0064 (19)	0.004 (2)	−0.008 (3)
C20	0.018 (2)	0.027 (2)	0.064 (4)	0.0064 (19)	0.004 (2)	−0.008 (3)
C20'	0.011 (2)	0.033 (2)	0.053 (3)	0.0018 (19)	0.000 (2)	−0.021 (2)

Geometric parameters (Å, º) top

S1—C17	1.723 (4)	C7—C8	1.395 (5)
S1—C20	1.727 (5)	C7—H7	0.9500
S1'—C17	1.695 (9)	C8—C9	1.408 (5)
S1'—C20'	1.713 (10)	C8—H8	0.9500
N1—C15	1.150 (5)	C9—C10	1.486 (5)
N2—C12	1.351 (5)	C10—C11	1.400 (5)
N2—H1	0.882 (10)	C11—C12	1.422 (5)
N2—H2	0.880 (10)	C11—C15	1.462 (5)
N3—C16	1.146 (5)	C12—C13	1.407 (5)
C1—C14	1.369 (5)	C13—C16	1.437 (5)
C1—C10	1.410 (5)	C13—C14	1.439 (5)
C1—C2	1.513 (5)	C14—C17	1.481 (5)
C2—C3	1.534 (5)	C17—C18	1.329 (6)
C2—H2A	0.9900	C17—C18'	1.367 (9)
C2—H2B	0.9900	C18—C19	1.445 (6)
C3—C4	1.531 (6)	C18—H18	0.9500
C3—H3A	0.9900	C18'—C19'	1.427 (9)
C3—H3B	0.9900	C18'—H18'	0.9500
C4—C5	1.364 (6)	C19—C20	1.354 (6)
C4—C9	1.408 (5)	C19—H19	0.9500
C5—C6	1.390 (6)	C19'—C20'	1.360 (9)
C5—H5	0.9500	C19'—H19'	0.9500
C6—C7	1.367 (6)	C20—H20	0.9500
C6—H6	0.9500	C20'—H20'	0.9500

C17—S1—C20	92.0 (2)	C1—C10—C9	118.4 (3)
C17—S1'—C20'	93.0 (5)	C10—C11—C12	121.9 (3)
C12—N2—H1	121 (2)	C10—C11—C15	124.5 (3)
C12—N2—H2	126 (3)	C12—C11—C15	113.5 (3)
H1—N2—H2	113 (4)	N2—C12—C13	121.8 (3)
C14—C1—C10	120.8 (3)	N2—C12—C11	121.2 (3)
C14—C1—C2	121.6 (3)	C13—C12—C11	117.0 (3)
C10—C1—C2	117.7 (3)	C12—C13—C16	117.9 (3)
C1—C2—C3	109.1 (3)	C12—C13—C14	121.2 (3)
C1—C2—H2A	109.9	C16—C13—C14	120.9 (3)
C3—C2—H2A	109.9	C1—C14—C13	119.6 (3)
C1—C2—H2B	109.9	C1—C14—C17	127.0 (3)
C3—C2—H2B	109.9	C13—C14—C17	113.3 (3)
H2A—C2—H2B	108.3	N1—C15—C11	172.9 (4)
C4—C3—C2	109.5 (3)	N3—C16—C13	176.6 (4)
C4—C3—H3A	109.8	C18—C17—C14	126.9 (4)
C2—C3—H3A	109.8	C18'—C17—C14	115.1 (11)
C4—C3—H3B	109.8	C18'—C17—S1'	111.3 (7)
C2—C3—H3B	109.8	C14—C17—S1'	133.6 (8)
H3A—C3—H3B	108.2	C18—C17—S1	111.5 (3)
C5—C4—C9	120.4 (4)	C14—C17—S1	121.6 (3)
C5—C4—C3	121.6 (4)	C17—C18—C19	113.4 (4)
C9—C4—C3	117.9 (4)	C17—C18—H18	123.3
C4—C5—C6	120.5 (4)	C19—C18—H18	123.3
C4—C5—H5	119.7	C17—C18'—C19'	112.4 (6)
C6—C5—H5	119.7	C17—C18'—H18'	123.8
C7—C6—C5	120.2 (4)	C19'—C18'—H18'	123.8
C7—C6—H6	119.9	C20—C19—C18	112.1 (4)
C5—C6—H6	119.9	C20—C19—H19	124.0
C6—C7—C8	120.5 (4)	C18—C19—H19	124.0
C6—C7—H7	119.8	C20'—C19'—C18'	112.7 (7)
C8—C7—H7	119.8	C20'—C19'—H19'	123.7
C7—C8—C9	119.6 (4)	C18'—C19'—H19'	123.7
C7—C8—H8	120.2	C19—C20—S1	111.1 (3)
C9—C8—H8	120.2	C19—C20—H20	124.5
C8—C9—C4	118.6 (4)	S1—C20—H20	124.5
C8—C9—C10	122.1 (3)	C19'—C20'—S1'	110.8 (8)
C4—C9—C10	119.3 (3)	C19'—C20'—H20'	124.6
C11—C10—C1	119.4 (3)	S1'—C20'—H20'	124.6
C11—C10—C9	122.2 (3)

C14—C1—C2—C3	−135.7 (4)	C2—C1—C14—C13	−178.3 (3)
C10—C1—C2—C3	43.4 (5)	C10—C1—C14—C17	−174.1 (3)
C1—C2—C3—C4	−58.1 (4)	C2—C1—C14—C17	5.0 (6)
C2—C3—C4—C5	−142.1 (4)	C12—C13—C14—C1	−2.2 (5)
C2—C3—C4—C9	34.1 (5)	C16—C13—C14—C1	−179.3 (3)
C9—C4—C5—C6	−0.3 (6)	C12—C13—C14—C17	174.9 (3)
C3—C4—C5—C6	175.8 (4)	C16—C13—C14—C17	−2.2 (5)
C4—C5—C6—C7	−2.3 (6)	C1—C14—C17—C18	−118.5 (4)
C5—C6—C7—C8	1.5 (6)	C13—C14—C17—C18	64.6 (3)
C6—C7—C8—C9	1.8 (6)	C1—C14—C17—C18'	62.6 (12)
C7—C8—C9—C4	−4.3 (5)	C13—C14—C17—C18'	−114.3 (11)
C7—C8—C9—C10	175.3 (3)	C1—C14—C17—S1'	−117.4 (11)
C5—C4—C9—C8	3.6 (6)	C13—C14—C17—S1'	65.7 (11)
C3—C4—C9—C8	−172.7 (4)	C1—C14—C17—S1	61.6 (4)
C5—C4—C9—C10	−176.1 (4)	C13—C14—C17—S1	−115.3 (3)
C3—C4—C9—C10	7.6 (5)	C20'—S1'—C17—C18	−173 (8)
C14—C1—C10—C11	−0.1 (5)	C20'—S1'—C17—C18'	0.1 (3)
C2—C1—C10—C11	−179.2 (3)	C20'—S1'—C17—C14	−179.92 (19)
C14—C1—C10—C9	177.3 (3)	C20'—S1'—C17—S1	1.0 (10)
C2—C1—C10—C9	−1.8 (5)	C20—S1—C17—C18	−0.9 (2)
C8—C9—C10—C11	−28.0 (6)	C20—S1—C17—C18'	171 (9)
C4—C9—C10—C11	151.7 (4)	C20—S1—C17—C14	178.99 (15)
C8—C9—C10—C1	154.7 (4)	C20—S1—C17—S1'	−1.8 (8)
C4—C9—C10—C1	−25.6 (5)	C18'—C17—C18—C19	0.2 (14)
C1—C10—C11—C12	−3.0 (5)	C14—C17—C18—C19	−178.7 (2)
C9—C10—C11—C12	179.8 (3)	S1'—C17—C18—C19	8 (7)
C1—C10—C11—C15	172.9 (3)	S1—C17—C18—C19	1.2 (3)
C9—C10—C11—C15	−4.3 (6)	C18—C17—C18'—C19'	1.0 (12)
C10—C11—C12—N2	−178.5 (3)	C14—C17—C18'—C19'	180.0 (3)
C15—C11—C12—N2	5.2 (5)	S1'—C17—C18'—C19'	0.0 (3)
C10—C11—C12—C13	3.3 (5)	S1—C17—C18'—C19'	−8 (9)
C15—C11—C12—C13	−173.0 (3)	C17—C18—C19—C20	−1.0 (4)
N2—C12—C13—C16	−1.7 (5)	C17—C18'—C19'—C20'	−0.1 (5)
C11—C12—C13—C16	176.5 (3)	C18—C19—C20—S1	0.2 (4)
N2—C12—C13—C14	−178.9 (3)	C17—S1—C20—C19	0.4 (3)
C11—C12—C13—C14	−0.7 (5)	C18'—C19'—C20'—S1'	0.1 (6)
C10—C1—C14—C13	2.6 (6)	C17—S1'—C20'—C19'	−0.1 (5)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C4–C9 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1···N3ⁱ	0.88 (3)	2.18 (3)	3.016 (5)	160 (3)
C6—H6···Cg1ⁱⁱ	0.95	2.85	3.660 (5)	144

Symmetry codes: (i) −x+1, −y, −z+1; (ii) −x+1, y+1/2, −z+3/2.

Experimental details

Crystal data
Chemical formula	C₂₀H₁₃N₃S
M_r	327.39
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	9.7882 (10), 7.1199 (7), 22.746 (3)
β (°)	93.171 (11)
V (Å³)	1582.8 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.21
Crystal size (mm)	0.30 × 0.06 × 0.03

Data collection
Diffractometer	Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2011)
T_min, T_max	0.940, 0.994
No. of measured, independent and observed [I > 2σ(I)] reflections	5527, 2805, 1778
R_int	0.056
(sin θ/λ)_max (Å⁻¹)	0.596

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.066, 0.164, 1.03
No. of reflections	2805
No. of parameters	236
No. of restraints	56
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.67, −0.55

Computer programs: CrysAlis PRO (Agilent, 2011), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C4–C9 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1···N3ⁱ	0.88 (3)	2.18 (3)	3.016 (5)	160 (3)
C6—H6···Cg1ⁱⁱ	0.95	2.85	3.660 (5)	144

Symmetry codes: (i) −x+1, −y, −z+1; (ii) −x+1, y+1/2, −z+3/2.

Footnotes

‡Additional correspondence author, e-mail: aasiri2@kau.edu.sa.

Acknowledgements

The authors are grateful to the Center of Excellence for Advanced Materials Research and the Chemistry Department at King Abdulaziz University for providing the research facilities. We also thank the Ministry of Higher Education (Malaysia) for funding structural studies through the High-Impact Research scheme (UM.C/HIR/MOHE/SC/12).

References

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Volume 68| Part 4| April 2012| Pages o1027-o1028

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