3-Amino-4-(1,3-benzoxazol-2-yl)-5-(cyclo-hexyl-amino)-thio-phene-2-carbo-nitrile.

In the title compound, C18H18N4OS, the cyclo-hexyl ring adopts a chair conformation. The other rings of this compound lie almost in the same plane, with a mean deviation of 0.03 (2) Å from the least-squares plane defined by the 14 constituent atoms. There are intra-molecular N-H⋯N and N-H⋯O hydrogen bonds, as well as inter-molecular N-H⋯N hydrogen bonds, which link the mol-ecules into centrosymmetric dimers.

Related literature

For the pharmacological and biological activities of benzoxazole derivatives, see: Isomura et al. (1983 ▶); Cheng et al.(1993 ▶); Koci et al. (2002 ▶); Hoffman et al. (1993 ▶); Arpaci et al. (2002 ▶). For the synthesis and a similar structure, see: Youssef et al. (2011 ▶); Belhouchet et al. (2012 ▶).

Experimental

Crystal data

C18H18N4OS

M = 338.42

Monoclinic,

a = 24.270 (5) Å

b = 6.193 (5) Å

c = 23.578 (5) Å

β = 107.554 (5)°

V = 3379 (3) Å3

Z = 8

Mo Kα radiation

μ = 0.20 mm−1

T = 293 K

0.3 × 0.25 × 0.22 mm

Data collection

Bruker APEXII area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.655, T max = 0.746

13506 measured reflections

2961 independent reflections

1904 reflections with I > 2σ(I)

R int = 0.049

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.112

S = 1.01

2961 reflections

230 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.17 e Å−3

Δρmin = −0.17 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶) and DIAMOND (Brandenburg, 1998 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813019880/bv2222sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813019880/bv2222Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813019880/bv2222Isup4.cml

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

C18H18N4OS	F(000) = 1424
Mr = 338.42	Dx = 1.331 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 2961 reflections
a = 24.270 (5) Å	θ = 1.8–24.9°
b = 6.193 (5) Å	µ = 0.20 mm−1
c = 23.578 (5) Å	T = 293 K
β = 107.554 (5)°	Parallelepipedic, violet
V = 3379 (3) Å3	0.3 × 0.25 × 0.22 mm
Z = 8

Bruker APEXII area-detector diffractometer	2961 independent reflections
Radiation source: fine-focus sealed tube	1904 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.049
φ and ω scans	θmax = 24.9°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −28→27
Tmin = 0.655, Tmax = 0.746	k = −7→7
13506 measured reflections	l = −27→27

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.042	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.112	w = 1/[σ2(Fo2) + (0.0502P)2 + 0.4702P] where P = (Fo2 + 2Fc2)/3
S = 1.01	(Δ/σ)max < 0.001
2961 reflections	Δρmax = 0.17 e Å−3
230 parameters	Δρmin = −0.17 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0009 (2)

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	0.55009 (3)	0.30537 (10)	0.19986 (3)	0.0550 (3)
O1	0.62688 (7)	−0.2687 (2)	0.09537 (7)	0.0517 (5)
N1	0.47339 (13)	0.5797 (5)	0.05475 (13)	0.0976 (10)
N2	0.55845 (11)	0.0864 (5)	0.04725 (11)	0.0593 (7)
N3	0.61458 (10)	−0.0165 (4)	0.26076 (9)	0.0521 (6)
N4	0.65779 (8)	−0.3092 (3)	0.19499 (8)	0.0432 (5)
C1	0.50228 (12)	0.4550 (5)	0.08608 (13)	0.0643 (8)
C2	0.53698 (10)	0.3009 (4)	0.12313 (11)	0.0501 (6)
C3	0.56239 (10)	0.1264 (4)	0.10435 (11)	0.0456 (6)
C4	0.59338 (10)	−0.0064 (3)	0.15318 (10)	0.0423 (6)
C5	0.59027 (10)	0.0711 (3)	0.20748 (11)	0.0436 (6)
C6	0.62674 (10)	−0.1949 (4)	0.15031 (10)	0.0422 (6)
C7	0.66194 (10)	−0.4503 (4)	0.10807 (11)	0.0464 (6)
C8	0.67552 (12)	−0.5875 (4)	0.06869 (12)	0.0610 (7)
H8	0.6620	−0.5669	0.0277	0.073*
C9	0.71069 (12)	−0.7582 (4)	0.09423 (14)	0.0657 (8)
H9	0.7211	−0.8572	0.0697	0.079*
C10	0.73088 (11)	−0.7869 (4)	0.15490 (13)	0.0607 (7)
H10	0.7548	−0.9039	0.1701	0.073*
C11	0.71652 (10)	−0.6462 (4)	0.19378 (12)	0.0539 (7)
H11	0.7302	−0.6660	0.2348	0.065*
C12	0.68079 (10)	−0.4743 (3)	0.16885 (10)	0.0433 (6)
C13	0.61259 (11)	0.0713 (4)	0.31737 (10)	0.0462 (6)
H13	0.5760	0.1493	0.3105	0.055*
C14	0.61355 (13)	−0.1124 (4)	0.36007 (12)	0.0614 (7)
H14A	0.5798	−0.2028	0.3439	0.074*
H14B	0.6476	−0.2005	0.3642	0.074*
C15	0.61409 (14)	−0.0298 (4)	0.42067 (12)	0.0698 (8)
H15A	0.5779	0.0433	0.4173	0.084*
H15B	0.6173	−0.1511	0.4475	0.084*
C16	0.66333 (14)	0.1232 (4)	0.44618 (12)	0.0736 (9)
H16A	0.6997	0.0473	0.4530	0.088*
H16B	0.6614	0.1777	0.4841	0.088*
C17	0.66063 (15)	0.3097 (4)	0.40402 (12)	0.0768 (9)
H17A	0.6934	0.4046	0.4203	0.092*
H17B	0.6256	0.3922	0.3997	0.092*
C18	0.66133 (12)	0.2272 (4)	0.34334 (12)	0.0625 (8)
H18A	0.6580	0.3485	0.3165	0.075*
H18B	0.6979	0.1559	0.3473	0.075*
H1N2	0.5767 (13)	−0.030 (4)	0.0372 (12)	0.076 (10)*
H2N2	0.5435 (12)	0.177 (4)	0.0194 (13)	0.075 (10)*
H1N3	0.6341 (11)	−0.132 (4)	0.2608 (11)	0.067 (9)*

	U11	U22	U33	U12	U13	U23
S1	0.0570 (5)	0.0570 (4)	0.0565 (5)	0.0136 (3)	0.0255 (3)	0.0145 (3)
O1	0.0574 (11)	0.0541 (10)	0.0389 (10)	0.0030 (8)	0.0075 (8)	0.0010 (8)
N1	0.106 (2)	0.111 (2)	0.084 (2)	0.0561 (18)	0.0410 (17)	0.0446 (17)
N2	0.0645 (16)	0.0656 (17)	0.0407 (16)	0.0077 (13)	0.0052 (12)	0.0114 (13)
N3	0.0647 (15)	0.0519 (14)	0.0394 (14)	0.0158 (11)	0.0155 (11)	0.0076 (11)
N4	0.0461 (12)	0.0434 (11)	0.0366 (12)	0.0030 (9)	0.0070 (9)	0.0029 (9)
C1	0.0602 (19)	0.0753 (19)	0.064 (2)	0.0181 (15)	0.0288 (15)	0.0232 (16)
C2	0.0437 (15)	0.0552 (15)	0.0529 (17)	0.0115 (12)	0.0168 (12)	0.0214 (13)
C3	0.0393 (14)	0.0542 (15)	0.0410 (16)	−0.0047 (11)	0.0085 (12)	0.0104 (12)
C4	0.0433 (14)	0.0424 (13)	0.0383 (15)	−0.0018 (11)	0.0078 (11)	0.0054 (11)
C5	0.0418 (14)	0.0443 (13)	0.0446 (16)	−0.0004 (11)	0.0126 (12)	0.0072 (12)
C6	0.0422 (14)	0.0460 (13)	0.0370 (15)	−0.0083 (11)	0.0096 (11)	−0.0027 (12)
C7	0.0466 (15)	0.0455 (14)	0.0460 (16)	−0.0011 (11)	0.0122 (12)	−0.0024 (12)
C8	0.0661 (19)	0.0665 (17)	0.0491 (17)	−0.0009 (15)	0.0154 (14)	−0.0073 (14)
C9	0.0667 (19)	0.0626 (18)	0.072 (2)	0.0009 (15)	0.0280 (17)	−0.0172 (15)
C10	0.0555 (17)	0.0545 (16)	0.074 (2)	0.0063 (13)	0.0223 (15)	0.0004 (15)
C11	0.0540 (17)	0.0553 (16)	0.0504 (17)	0.0060 (13)	0.0124 (13)	0.0057 (13)
C12	0.0424 (15)	0.0441 (14)	0.0423 (16)	−0.0066 (11)	0.0111 (12)	−0.0022 (11)
C13	0.0537 (16)	0.0468 (14)	0.0431 (16)	0.0072 (12)	0.0221 (12)	0.0067 (11)
C14	0.085 (2)	0.0515 (15)	0.0513 (18)	−0.0059 (14)	0.0261 (15)	0.0081 (13)
C15	0.103 (2)	0.0629 (17)	0.0560 (19)	0.0047 (17)	0.0423 (17)	0.0149 (14)
C16	0.105 (3)	0.0748 (19)	0.0445 (18)	0.0059 (18)	0.0274 (17)	−0.0021 (15)
C17	0.109 (3)	0.0680 (19)	0.059 (2)	−0.0191 (17)	0.0346 (18)	−0.0087 (16)
C18	0.078 (2)	0.0593 (16)	0.0576 (18)	−0.0065 (14)	0.0325 (15)	0.0038 (14)

S1—C5	1.727 (3)	C9—H9	0.9300
S1—C2	1.740 (3)	C10—C11	1.383 (3)
O1—C6	1.375 (3)	C10—H10	0.9300
O1—C7	1.387 (3)	C11—C12	1.387 (3)
N1—C1	1.150 (3)	C11—H11	0.9300
N2—C3	1.343 (3)	C13—C18	1.506 (3)
N2—H1N2	0.92 (3)	C13—C14	1.515 (3)
N2—H2N2	0.86 (3)	C13—H13	0.9800
N3—C5	1.332 (3)	C14—C15	1.514 (4)
N3—C13	1.455 (3)	C14—H14A	0.9700
N3—H1N3	0.86 (2)	C14—H14B	0.9700
N4—C6	1.304 (3)	C15—C16	1.502 (4)
N4—C12	1.394 (3)	C15—H15A	0.9700
C1—C2	1.392 (4)	C15—H15B	0.9700
C2—C3	1.382 (3)	C16—C17	1.513 (4)
C3—C4	1.430 (3)	C16—H16A	0.9700
C4—C5	1.391 (3)	C16—H16B	0.9700
C4—C6	1.434 (3)	C17—C18	1.524 (3)
C7—C8	1.370 (3)	C17—H17A	0.9700
C7—C12	1.375 (3)	C17—H17B	0.9700
C8—C9	1.378 (4)	C18—H18A	0.9700
C8—H8	0.9300	C18—H18B	0.9700
C9—C10	1.377 (4)
C5—S1—C2	90.89 (11)	C7—C12—C11	119.6 (2)
C6—O1—C7	104.00 (17)	C7—C12—N4	109.3 (2)
C3—N2—H1N2	120.8 (18)	C11—C12—N4	131.2 (2)
C3—N2—H2N2	122.0 (19)	N3—C13—C18	111.91 (19)
H1N2—N2—H2N2	116 (3)	N3—C13—C14	109.3 (2)
C5—N3—C13	125.8 (2)	C18—C13—C14	111.0 (2)
C5—N3—H1N3	115.3 (18)	N3—C13—H13	108.2
C13—N3—H1N3	118.9 (18)	C18—C13—H13	108.2
C6—N4—C12	104.58 (19)	C14—C13—H13	108.2
N1—C1—C2	178.9 (4)	C15—C14—C13	111.6 (2)
C3—C2—C1	125.4 (2)	C15—C14—H14A	109.3
C3—C2—S1	112.71 (17)	C13—C14—H14A	109.3
C1—C2—S1	121.8 (2)	C15—C14—H14B	109.3
N2—C3—C2	124.1 (2)	C13—C14—H14B	109.3
N2—C3—C4	124.2 (2)	H14A—C14—H14B	108.0
C2—C3—C4	111.7 (2)	C16—C15—C14	111.8 (2)
C5—C4—C3	112.4 (2)	C16—C15—H15A	109.3
C5—C4—C6	120.9 (2)	C14—C15—H15A	109.3
C3—C4—C6	126.7 (2)	C16—C15—H15B	109.3
N3—C5—C4	126.6 (2)	C14—C15—H15B	109.3
N3—C5—S1	121.08 (19)	H15A—C15—H15B	107.9
C4—C5—S1	112.33 (17)	C15—C16—C17	110.3 (3)
N4—C6—O1	114.6 (2)	C15—C16—H16A	109.6
N4—C6—C4	126.9 (2)	C17—C16—H16A	109.6
O1—C6—C4	118.5 (2)	C15—C16—H16B	109.6
C8—C7—C12	124.6 (2)	C17—C16—H16B	109.6
C8—C7—O1	127.8 (2)	H16A—C16—H16B	108.1
C12—C7—O1	107.6 (2)	C16—C17—C18	110.5 (2)
C7—C8—C9	115.1 (3)	C16—C17—H17A	109.6
C7—C8—H8	122.5	C18—C17—H17A	109.6
C9—C8—H8	122.5	C16—C17—H17B	109.6
C10—C9—C8	122.2 (3)	C18—C17—H17B	109.6
C10—C9—H9	118.9	H17A—C17—H17B	108.1
C8—C9—H9	118.9	C13—C18—C17	111.5 (2)
C9—C10—C11	121.7 (3)	C13—C18—H18A	109.3
C9—C10—H10	119.2	C17—C18—H18A	109.3
C11—C10—H10	119.2	C13—C18—H18B	109.3
C10—C11—C12	116.9 (2)	C17—C18—H18B	109.3
C10—C11—H11	121.5	H18A—C18—H18B	108.0
C12—C11—H11	121.5
N1—C1—C2—C3	25 (16)	C3—C4—C6—O1	−4.7 (3)
N1—C1—C2—S1	−152 (16)	C6—O1—C7—C8	178.5 (2)
C5—S1—C2—C3	0.11 (19)	C6—O1—C7—C12	−0.3 (2)
C5—S1—C2—C1	177.5 (2)	C12—C7—C8—C9	−0.1 (4)
C1—C2—C3—N2	2.4 (4)	O1—C7—C8—C9	−178.7 (2)
S1—C2—C3—N2	179.76 (19)	C7—C8—C9—C10	−0.5 (4)
C1—C2—C3—C4	−177.6 (2)	C8—C9—C10—C11	0.5 (4)
S1—C2—C3—C4	−0.3 (3)	C9—C10—C11—C12	0.0 (4)
N2—C3—C4—C5	−179.7 (2)	C8—C7—C12—C11	0.6 (4)
C2—C3—C4—C5	0.3 (3)	O1—C7—C12—C11	179.46 (19)
N2—C3—C4—C6	2.7 (4)	C8—C7—C12—N4	−178.7 (2)
C2—C3—C4—C6	−177.3 (2)	O1—C7—C12—N4	0.2 (3)
C13—N3—C5—C4	177.6 (2)	C10—C11—C12—C7	−0.5 (3)
C13—N3—C5—S1	−2.1 (3)	C10—C11—C12—N4	178.6 (2)
C3—C4—C5—N3	−180.0 (2)	C6—N4—C12—C7	0.0 (2)
C6—C4—C5—N3	−2.2 (4)	C6—N4—C12—C11	−179.1 (2)
C3—C4—C5—S1	−0.2 (3)	C5—N3—C13—C18	−88.0 (3)
C6—C4—C5—S1	177.51 (16)	C5—N3—C13—C14	148.6 (2)
C2—S1—C5—N3	179.8 (2)	N3—C13—C14—C15	177.6 (2)
C2—S1—C5—C4	0.06 (19)	C18—C13—C14—C15	53.7 (3)
C12—N4—C6—O1	−0.3 (2)	C13—C14—C15—C16	−55.2 (3)
C12—N4—C6—C4	179.4 (2)	C14—C15—C16—C17	56.8 (3)
C7—O1—C6—N4	0.4 (2)	C15—C16—C17—C18	−57.1 (3)
C7—O1—C6—C4	−179.33 (19)	N3—C13—C18—C17	−177.2 (2)
C5—C4—C6—N4	−1.7 (4)	C14—C13—C18—C17	−54.8 (3)
C3—C4—C6—N4	175.7 (2)	C16—C17—C18—C13	56.8 (3)
C5—C4—C6—O1	178.0 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1N2···O1	0.92 (3)	2.13 (3)	2.783 (4)	127 (2)
N2—H2N2···N1i	0.86 (3)	2.25 (3)	3.088 (4)	166 (3)
N3—H1N3···N4	0.86 (2)	2.12 (3)	2.787 (3)	135 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H1N2⋯O1	0.92 (3)	2.13 (3)	2.783 (4)	127 (2)
N2—H2N2⋯N1i	0.86 (3)	2.25 (3)	3.088 (4)	166 (3)
N3—H1N3⋯N4	0.86 (2)	2.12 (3)	2.787 (3)	135 (2)

Symmetry code: (i) .