(2R)-N-[5-(4-Chloro-phen-yl)-1,3,4-thia-diazol-2-yl]-2-(cinnamoylamino)propanamide.

In the title compound, C(20)H(17)ClN(4)O(2)S, the dihedral angle between the two benzene rings is 65.9 (1)°; the corresponding angle between the 4-chloro-phenyl and thia-diazole rings is 3.4 (8)°. The conformations of the N-H and C=O bonds are anti with respect to each other. The enone groups show a trans configuration. The structure displays intermolecular N-H⋯O, C-H⋯N, C-H⋯S and C-H⋯O hydrogen bonding.

Related literature

For 1,3,4-thia­diazole scaffold compounds and their biological activity, see: Tu et al. (2008 ▶). For the synthesis, see: Foroumadi et al. (1999 ▶); Levy & Palmer (1942 ▶); Song et al. (1992 ▶). For related structures, see: Fun et al. (2008 ▶); Gowda et al. (2008 ▶) Thiruvalluvar et al. (2008 ▶).

Experimental

Crystal data

C20H17ClN4O2S

M = 412.89

Orthorhombic,

a = 6.6324 (15) Å

b = 8.575 (2) Å

c = 34.367 (8) Å

V = 1954.6 (8) Å3

Z = 4

Mo Kα radiation

μ = 0.33 mm−1

T = 296 (2) K

0.41 × 0.17 × 0.07 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: none

14721 measured reflections

4706 independent reflections

2807 reflections with I > 2σ(I)

R int = 0.046

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.099

S = 1.02

4706 reflections

254 parameters

H-atom parameters constrained

Δρmax = 0.15 e Å−3

Δρmin = −0.20 e Å−3

Absolute structure: Flack (1983 ▶), 1876 Friedel pairs

Flack parameter: −0.12 (7)

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: APEX2; software used to prepare material for publication: APEX2 and publCIF (Westrip, 2008 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808030353/gw2052sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808030353/gw2052Isup2.hkl

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

C20H17ClN4O2S	Dx = 1.403 Mg m−3
Mr = 412.89	Melting point: 480 K
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 3308 reflections
a = 6.6324 (15) Å	θ = 2.4–21.0°
b = 8.575 (2) Å	µ = 0.33 mm−1
c = 34.367 (8) Å	T = 296 K
V = 1954.6 (8) Å3	Bolck, colourless
Z = 4	0.41 × 0.18 × 0.07 mm
F(000) = 856

Bruker SMART CCD area-detector diffractometer	2807 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.046
graphite	θmax = 28.4°, θmin = 2.4°
φ and ω scans	h = −8→8
14721 measured reflections	k = −11→11
4706 independent reflections	l = −45→44

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)] = 0.043	H-atom parameters constrained
wR(F2) = 0.099	w = 1/[σ2(Fo2) + (0.0226P)2 + 0.0747P] where P = (Fo2 + 2Fc2)/3
S = 1.02	(Δ/σ)max < 0.001
4706 reflections	Δρmax = 0.15 e Å−3
254 parameters	Δρmin = −0.20 e Å−3
0 restraints	Absolute structure: Flack (1983), 1876 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: −0.12 (7)

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
C1	0.6789 (5)	0.2710 (4)	0.19355 (8)	0.0782 (9)
H1B	0.6067	0.2030	0.1777	0.094*
C2	0.6159 (6)	0.2979 (4)	0.23129 (10)	0.0996 (13)
H2B	0.5024	0.2468	0.2408	0.120*
C3	0.7184 (6)	0.3981 (5)	0.25465 (9)	0.0977 (12)
H3B	0.6745	0.4158	0.2800	0.117*
C4	0.8862 (6)	0.4732 (4)	0.24098 (8)	0.0937 (12)
H4B	0.9551	0.5434	0.2568	0.112*
C5	0.9526 (5)	0.4443 (4)	0.20360 (8)	0.0756 (9)
H5A	1.0692	0.4927	0.1947	0.091*
C6	0.8481 (5)	0.3443 (3)	0.17924 (7)	0.0613 (8)
C7	0.9087 (5)	0.3172 (3)	0.13882 (7)	0.0612 (8)
H7A	0.8246	0.2533	0.1242	0.073*
C8	1.0669 (4)	0.3722 (3)	0.12100 (7)	0.0584 (7)
H8A	1.1579	0.4314	0.1353	0.070*
C9	1.1094 (4)	0.3464 (3)	0.07984 (7)	0.0523 (7)
C10	1.3357 (4)	0.4044 (3)	0.02573 (6)	0.0483 (6)
H10A	1.3421	0.2934	0.0190	0.058*
C11	1.5445 (4)	0.4755 (3)	0.02035 (8)	0.0626 (8)
H11A	1.6384	0.4245	0.0374	0.094*
H11B	1.5397	0.5847	0.0264	0.094*
H11C	1.5870	0.4619	−0.0061	0.094*
C12	1.1836 (4)	0.4831 (3)	−0.00072 (7)	0.0494 (6)
C13	1.0385 (4)	0.4721 (3)	−0.06496 (7)	0.0471 (6)
C14	0.7573 (4)	0.5583 (3)	−0.10172 (6)	0.0494 (6)
C15	0.5693 (4)	0.6256 (3)	−0.11652 (7)	0.0490 (6)
C16	0.4931 (5)	0.5842 (3)	−0.15249 (7)	0.0639 (7)
H16A	0.5625	0.5115	−0.1675	0.077*
C17	0.3163 (5)	0.6479 (3)	−0.16687 (8)	0.0669 (8)
H17A	0.2679	0.6198	−0.1913	0.080*
C18	0.2142 (4)	0.7538 (3)	−0.14421 (8)	0.0589 (7)
C19	0.2848 (5)	0.7959 (3)	−0.10843 (8)	0.0637 (8)
H19A	0.2137	0.8676	−0.0935	0.076*
C20	0.4600 (4)	0.7328 (3)	−0.09455 (8)	0.0591 (7)
H20A	0.5068	0.7619	−0.0701	0.071*
Cl1	−0.00738 (13)	0.83679 (9)	−0.16181 (2)	0.0835 (3)
N1	1.2732 (3)	0.4188 (2)	0.06588 (5)	0.0537 (5)
H1A	1.3436	0.4758	0.0813	0.064*
N2	1.1824 (3)	0.4305 (2)	−0.03825 (5)	0.0525 (5)
H2A	1.2768	0.3681	−0.0455	0.063*
N3	1.0265 (4)	0.4021 (3)	−0.09856 (6)	0.0590 (6)
N4	0.8619 (4)	0.4535 (2)	−0.12001 (6)	0.0585 (6)
O1	1.0027 (3)	0.2679 (2)	0.05768 (5)	0.0672 (5)
O2	1.0712 (3)	0.5869 (2)	0.00979 (5)	0.0638 (5)
S1	0.85258 (10)	0.60793 (7)	−0.056449 (17)	0.05201 (18)

	U11	U22	U33	U12	U13	U23
C1	0.081 (3)	0.090 (2)	0.0635 (18)	−0.017 (2)	0.0140 (18)	−0.0047 (16)
C2	0.112 (4)	0.116 (3)	0.070 (2)	−0.030 (3)	0.029 (2)	−0.004 (2)
C3	0.110 (3)	0.124 (3)	0.0594 (19)	−0.021 (3)	0.021 (2)	−0.006 (2)
C4	0.113 (3)	0.114 (3)	0.0541 (18)	−0.028 (3)	0.0073 (19)	−0.0090 (18)
C5	0.080 (2)	0.093 (2)	0.0539 (17)	−0.0173 (19)	0.0071 (16)	−0.0014 (15)
C6	0.068 (2)	0.0673 (18)	0.0484 (14)	−0.0030 (16)	0.0023 (14)	0.0034 (12)
C7	0.075 (2)	0.0623 (16)	0.0465 (15)	−0.0090 (16)	−0.0007 (15)	0.0002 (13)
C8	0.0591 (19)	0.0670 (17)	0.0490 (15)	−0.0077 (15)	0.0026 (13)	−0.0025 (13)
C9	0.0530 (19)	0.0535 (15)	0.0503 (14)	−0.0074 (13)	−0.0006 (13)	0.0012 (12)
C10	0.0448 (15)	0.0539 (14)	0.0464 (13)	−0.0036 (14)	0.0008 (12)	−0.0019 (11)
C11	0.0491 (19)	0.0728 (18)	0.0658 (17)	−0.0078 (15)	0.0092 (14)	−0.0079 (14)
C12	0.0496 (18)	0.0524 (15)	0.0460 (14)	−0.0044 (13)	0.0050 (12)	−0.0053 (11)
C13	0.0461 (16)	0.0516 (13)	0.0437 (13)	0.0004 (12)	0.0065 (12)	−0.0024 (11)
C14	0.0524 (18)	0.0529 (15)	0.0428 (13)	−0.0032 (13)	0.0074 (12)	−0.0003 (11)
C15	0.0502 (17)	0.0516 (14)	0.0453 (14)	−0.0025 (13)	0.0051 (12)	0.0000 (12)
C16	0.067 (2)	0.0747 (18)	0.0499 (15)	0.0125 (17)	0.0012 (15)	−0.0069 (13)
C17	0.065 (2)	0.081 (2)	0.0540 (15)	0.0083 (17)	−0.0075 (15)	−0.0055 (14)
C18	0.0460 (18)	0.0622 (17)	0.0686 (18)	0.0037 (14)	−0.0010 (14)	0.0109 (14)
C19	0.055 (2)	0.0669 (18)	0.0695 (18)	0.0050 (15)	0.0080 (15)	−0.0077 (14)
C20	0.056 (2)	0.0666 (17)	0.0545 (16)	0.0020 (16)	0.0009 (14)	−0.0103 (13)
Cl1	0.0582 (5)	0.0923 (6)	0.1001 (6)	0.0079 (4)	−0.0089 (5)	0.0129 (4)
N1	0.0521 (14)	0.0672 (13)	0.0417 (11)	−0.0115 (12)	−0.0006 (10)	−0.0046 (10)
N2	0.0508 (14)	0.0629 (13)	0.0439 (11)	0.0086 (11)	0.0030 (10)	−0.0048 (9)
N3	0.0611 (16)	0.0685 (13)	0.0472 (12)	0.0108 (13)	0.0006 (11)	−0.0074 (11)
N4	0.0591 (16)	0.0676 (13)	0.0488 (11)	0.0069 (13)	0.0014 (12)	−0.0090 (10)
O1	0.0605 (13)	0.0815 (12)	0.0595 (11)	−0.0230 (11)	0.0052 (11)	−0.0127 (10)
O2	0.0666 (13)	0.0715 (12)	0.0534 (10)	0.0174 (11)	−0.0024 (9)	−0.0166 (9)
S1	0.0507 (4)	0.0584 (4)	0.0469 (3)	0.0047 (3)	0.0040 (3)	−0.0059 (3)

C1—C6	1.377 (4)	C11—H11C	0.9600
C1—C2	1.382 (4)	C12—O2	1.216 (3)
C1—H1B	0.9300	C12—N2	1.367 (3)
C2—C3	1.359 (5)	C13—N3	1.304 (3)
C2—H2B	0.9300	C13—N2	1.372 (3)
C3—C4	1.369 (5)	C13—S1	1.721 (3)
C3—H3B	0.9300	C14—N4	1.298 (3)
C4—C5	1.380 (4)	C14—C15	1.465 (3)
C4—H4B	0.9300	C14—S1	1.732 (2)
C5—C6	1.384 (4)	C15—C16	1.382 (3)
C5—H5A	0.9300	C15—C20	1.393 (3)
C6—C7	1.465 (4)	C16—C17	1.385 (4)
C7—C8	1.303 (4)	C16—H16A	0.9300
C7—H7A	0.9300	C17—C18	1.375 (4)
C8—C9	1.459 (3)	C17—H17A	0.9300
C8—H8A	0.9300	C18—C19	1.364 (4)
C9—O1	1.239 (3)	C18—Cl1	1.741 (3)
C9—N1	1.340 (3)	C19—C20	1.368 (4)
C10—N1	1.446 (3)	C19—H19A	0.9300
C10—C12	1.517 (3)	C20—H20A	0.9300
C10—C11	1.524 (3)	N1—H1A	0.8600
C10—H10A	0.9800	N2—H2A	0.8600
C11—H11A	0.9600	N3—N4	1.389 (3)
C11—H11B	0.9600
C6—C1—C2	120.4 (3)	H11B—C11—H11C	109.5
C6—C1—H1B	119.8	O2—C12—N2	121.2 (2)
C2—C1—H1B	119.8	O2—C12—C10	123.8 (2)
C3—C2—C1	120.6 (4)	N2—C12—C10	115.0 (2)
C3—C2—H2B	119.7	N3—C13—N2	121.0 (2)
C1—C2—H2B	119.7	N3—C13—S1	114.7 (2)
C2—C3—C4	120.1 (3)	N2—C13—S1	124.11 (17)
C2—C3—H3B	120.0	N4—C14—C15	124.0 (2)
C4—C3—H3B	120.0	N4—C14—S1	114.2 (2)
C3—C4—C5	119.6 (3)	C15—C14—S1	121.72 (18)
C3—C4—H4B	120.2	C16—C15—C20	117.6 (2)
C5—C4—H4B	120.2	C16—C15—C14	121.4 (2)
C4—C5—C6	121.0 (3)	C20—C15—C14	121.0 (2)
C4—C5—H5A	119.5	C15—C16—C17	121.8 (3)
C6—C5—H5A	119.5	C15—C16—H16A	119.1
C1—C6—C5	118.3 (3)	C17—C16—H16A	119.1
C1—C6—C7	119.3 (3)	C18—C17—C16	118.4 (3)
C5—C6—C7	122.3 (3)	C18—C17—H17A	120.8
C8—C7—C6	127.5 (3)	C16—C17—H17A	120.8
C8—C7—H7A	116.2	C19—C18—C17	121.1 (3)
C6—C7—H7A	116.2	C19—C18—Cl1	119.6 (2)
C7—C8—C9	123.8 (3)	C17—C18—Cl1	119.3 (2)
C7—C8—H8A	118.1	C18—C19—C20	120.1 (3)
C9—C8—H8A	118.1	C18—C19—H19A	120.0
O1—C9—N1	119.7 (2)	C20—C19—H19A	120.0
O1—C9—C8	124.6 (3)	C19—C20—C15	121.0 (3)
N1—C9—C8	115.7 (2)	C19—C20—H20A	119.5
N1—C10—C12	110.1 (2)	C15—C20—H20A	119.5
N1—C10—C11	110.0 (2)	C9—N1—C10	122.3 (2)
C12—C10—C11	110.7 (2)	C9—N1—H1A	118.8
N1—C10—H10A	108.7	C10—N1—H1A	118.8
C12—C10—H10A	108.7	C12—N2—C13	123.3 (2)
C11—C10—H10A	108.7	C12—N2—H2A	118.3
C10—C11—H11A	109.5	C13—N2—H2A	118.3
C10—C11—H11B	109.5	C13—N3—N4	111.8 (2)
H11A—C11—H11B	109.5	C14—N4—N3	112.5 (2)
C10—C11—H11C	109.5	C13—S1—C14	86.70 (12)
H11A—C11—H11C	109.5
C6—C1—C2—C3	0.7 (6)	C16—C17—C18—C19	0.2 (4)
C1—C2—C3—C4	−0.3 (6)	C16—C17—C18—Cl1	179.5 (2)
C2—C3—C4—C5	−1.2 (6)	C17—C18—C19—C20	0.1 (4)
C3—C4—C5—C6	2.2 (5)	Cl1—C18—C19—C20	−179.2 (2)
C2—C1—C6—C5	0.2 (5)	C18—C19—C20—C15	0.2 (4)
C2—C1—C6—C7	−178.4 (3)	C16—C15—C20—C19	−0.8 (4)
C4—C5—C6—C1	−1.7 (5)	C14—C15—C20—C19	179.8 (2)
C4—C5—C6—C7	176.8 (3)	O1—C9—N1—C10	−2.3 (4)
C1—C6—C7—C8	−177.5 (3)	C8—C9—N1—C10	179.8 (2)
C5—C6—C7—C8	4.0 (5)	C12—C10—N1—C9	67.6 (3)
C6—C7—C8—C9	−176.3 (2)	C11—C10—N1—C9	−170.1 (2)
C7—C8—C9—O1	−1.3 (4)	O2—C12—N2—C13	−9.9 (4)
C7—C8—C9—N1	176.5 (3)	C10—C12—N2—C13	171.0 (2)
N1—C10—C12—O2	24.2 (3)	N3—C13—N2—C12	−170.0 (2)
C11—C10—C12—O2	−97.7 (3)	S1—C13—N2—C12	5.7 (3)
N1—C10—C12—N2	−156.8 (2)	N2—C13—N3—N4	175.5 (2)
C11—C10—C12—N2	81.4 (3)	S1—C13—N3—N4	−0.5 (3)
N4—C14—C15—C16	−2.3 (4)	C15—C14—N4—N3	−176.1 (2)
S1—C14—C15—C16	−179.3 (2)	S1—C14—N4—N3	1.1 (3)
N4—C14—C15—C20	177.1 (2)	C13—N3—N4—C14	−0.4 (3)
S1—C14—C15—C20	0.1 (3)	N3—C13—S1—C14	0.9 (2)
C20—C15—C16—C17	1.1 (4)	N2—C13—S1—C14	−175.0 (2)
C14—C15—C16—C17	−179.5 (2)	N4—C14—S1—C13	−1.2 (2)
C15—C16—C17—C18	−0.8 (4)	C15—C14—S1—C13	176.1 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O1i	0.86	1.94	2.802 (3)	175.
C7—H7A···O1	0.93	2.58	2.888 (3)	100.
C7—H7A···N3ii	0.93	2.54	3.446 (3)	164.
C11—H11C···S1iii	0.96	2.77	3.526 (3)	136.
C20—H20A···S1	0.93	2.69	3.105 (3)	108.
C20—H20A···O2iv	0.93	2.48	3.380 (3)	162.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O1i	0.86	1.94	2.802 (3)	175
C7—H7A⋯N3ii	0.93	2.54	3.446 (3)	164
C11—H11C⋯S1iii	0.96	2.77	3.526 (3)	136
C20—H20A⋯O2iv	0.93	2.48	3.380 (3)	162

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .