(2R)-N-[5-(4-Chloro­phen­yl)-1,3,4-thia­diazol-2-yl]-2-(cinnamoylamino)propanamide

Li, S.-H.; Huang, H.-M.; Kuang, B.-H.; Tu, G.-G.; Liu, C.-M.

doi:10.1107/S1600536808030353

organic compounds

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ISSN: 2056-9890

Volume 64| Part 10| October 2008| Page o2006

doi:10.1107/S1600536808030353

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(2R)-N-[5-(4-Chlorophenyl)-1,3,4-thiadiazol-2-yl]-2-(cinnamoylamino)propanamide

Shao-Hua Li,^a,^b Hui-Ming Huang,^b Bin-Hai Kuang,^b Guo-Gang Tu ^b ^* and Cheng-Mei Liu ^a ‡

^aState Key Laboratory of Food Science and Technology, Nanchang University, 330047 Nanchang, JiangXi, People's Republic of China, and ^bDepartment of Pharmacy, NanChang University Medical College, 330006 Nanchang, JiangXi, People's Republic of China
^*Correspondence e-mail: tugg199@yahoo.com

(Received 5 September 2008; accepted 22 September 2008; online 24 September 2008)

In the title compound, C₂₀H₁₇ClN₄O₂S, the dihedral angle between the two benzene rings is 65.9 (1)°; the corresponding angle between the 4-chlorophenyl and thiadiazole 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_r = 412.89
Orthorhombic, P 2₁ 2₁ 2₁
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[F² > 2σ(F²)] = 0.043
wR(F²) = 0.099
S = 1.02
4706 reflections
254 parameters
H-atom parameters constrained
Δρ_max = 0.15 e Å⁻³
Δρ_min = −0.20 e Å⁻³
Absolute structure: Flack (1983 ), 1876 Friedel pairs
Flack parameter: −0.12 (7)

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⋯O2^iv	0.93	2.48	3.380 (3)	162
Symmetry codes: (i) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z]$ ; (ii) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, -z]$ ; (iii) x+1, y, z; (iv) $[x-{\script{1\over 2}}, -y+{\script{3\over 2}}, -z]$ .

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 ).

Supporting information

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

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

checkCIF report

Comment top

In our previous work, 1,3,4-thiadiazole scaffold compounds and their biological activity have been studied (Tu et al., 2008). In view of the importance of these organic materials, the title compound (Fig. 1) was synthesized (Foroumadi et al., 1999; Levy & Palmer 1942; Song et al., 1992) and its crystal structure is reported here. The structure of title compound, C₂₀H₁₇ClN₄O₂S, has orthorhombic (P2₁2₁2₁) symmetry. The dihedral angles between the p-cholobenzene and thiadiazol rings is 3.4 (8) °, the corresponding values between the two benzene rings are measured to 65.9 (1)°. The conformations of the N—H and C=O bonds are anti with respect to each other. The enone groups are trans configurated. Bond lengths and angles are in normal ranges and comparable to those in related structures (Gowda et al., 2008; Fun et al., 2008; Thiruvalluvar et al., 2008). In the crystal structure, molecules are linked through intermolecular hydrogen bonds forming a three-dimensional network (Table 1, Figure 2).

Related literature top

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 top

N,N-Dicyclohexylcarbodiimide (5.7 mmol) was added to a cooled solution of N-cinnamoyl-D-alanine (5.6 mmol) and N-hydroxysuccinimide (5.6 mmol) in freshly distillation dioxane (30 ml). The reaction mixture was stirred overnight at room temperature. The insoluble material was filtered off and washed with cold dioxane. 2-Amino-5-(4-choloxyphenyl)-1,3,4-thiadiazole (5.5 mmol) was added to the filtrate and the reaction mixture was stirred for 48 hr at room temperature. The solvent was removed under reduced pressure. The residual was dissolved in EtOAc and the insoluble material was filtered off. The filtrate was washed successively with saturated Na₂CO₃ solution(20 ml, x 3), water(20 ml, x 1), 0.1 M HCl(20 ml, x 3) and water(20 ml, x 1). The organic layer evaporated in vacuo, the residual was recrystallized from methanol. Colorless block-shaped single crystals of the title compound suitable for X-ray diffraction analysis precipitated after several days.

Computing details top

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

Figures top

	Fig. 1. Molecular structure of the title compound. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. The crystal packing of title compound, viewed along the a axis with hydrogen bonds drawn as dashed lines.

(2R)-N-[5-(4-Chlorophenyl)-1,3,4-thiadiazol-2-yl]-2- (cinnamoylamino)propanamide top

Crystal data top

C₂₀H₁₇ClN₄O₂S	D_x = 1.403 Mg m⁻³
M_r = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0226P)² + 0.0747P] where P = (F_o² + 2F_c²)/3
S = 1.02	(Δ/σ)_max < 0.001
4706 reflections	Δρ_max = 0.15 e Å⁻³
254 parameters	Δρ_min = −0.20 e Å⁻³
0 restraints	Absolute structure: Flack (1983), 1876 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.12 (7)

Crystal data top

C₂₀H₁₇ClN₄O₂S	V = 1954.6 (8) Å³
M_r = 412.89	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 6.6324 (15) Å	µ = 0.33 mm⁻¹
b = 8.575 (2) Å	T = 296 K
c = 34.367 (8) Å	0.41 × 0.18 × 0.07 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	2807 reflections with I > 2σ(I)
14721 measured reflections	R_int = 0.046
4706 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.043	H-atom parameters constrained
wR(F²) = 0.099	Δρ_max = 0.15 e Å⁻³
S = 1.02	Δρ_min = −0.20 e Å⁻³
4706 reflections	Absolute structure: Flack (1983), 1876 Friedel pairs
254 parameters	Absolute structure parameter: −0.12 (7)
0 restraints

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
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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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···O2^iv	0.93	2.48	3.380 (3)	162

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

Experimental details

Crystal data
Chemical formula	C₂₀H₁₇ClN₄O₂S
M_r	412.89
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	296
a, b, c (Å)	6.6324 (15), 8.575 (2), 34.367 (8)
V (Å³)	1954.6 (8)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.33
Crystal size (mm)	0.41 × 0.18 × 0.07

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	14721, 4706, 2807
R_int	0.046
(sin θ/λ)_max (Å⁻¹)	0.668

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.043, 0.099, 1.02
No. of reflections	4706
No. of parameters	254
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.15, −0.20
Absolute structure	Flack (1983), 1876 Friedel pairs
Absolute structure parameter	−0.12 (7)

Computer programs: , SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), APEX2 (Bruker, 2004) and publCIF (Westrip, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O1ⁱ	0.86	1.94	2.802 (3)	174.9
C7—H7A···O1	0.93	2.58	2.888 (3)	100.2
C7—H7A···N3ⁱⁱ	0.93	2.54	3.446 (3)	164.4
C11—H11C···S1ⁱⁱⁱ	0.96	2.77	3.526 (3)	136.4
C20—H20A···S1	0.93	2.69	3.105 (3)	108.1
C20—H20A···O2^iv	0.93	2.48	3.380 (3)	162.2

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

Footnotes

‡Additional correspondence author, e-mail: lishaohua0131@yahoo.com.cn.

References

Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Foroumadi, A., Daneshtalab, M. & Shafiee, A. (1999). Arzneim. Forsch. 49, 1035–1038. CAS Google Scholar
Fun, H.-K., Chantrapromma, S., Patil, P. S., Karthikeyan, M. S. & Dharmaprakash, S. M. (2008). Acta Cryst. E64, o956–o957. Web of Science CSD CrossRef IUCr Journals Google Scholar
Gowda, B. T., Tokarčík, M., Kožíšek, J., Sowmya, B. P. & Fuess, H. (2008). Acta Cryst. E64, o950. Web of Science CSD CrossRef IUCr Journals Google Scholar
Levy, M. & Palmer, A. H. (1942). J. Biol. Chem. 146, 493–495. CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Song, K. S., Ishikawa, Y., Kobayashi, S., Sankawa, U. & Ebizuka, Y. (1992). Phytochemistry, 31, 823–826. CrossRef CAS Google Scholar
Thiruvalluvar, A., Subramanyam, M., Butcher, R. J., Karabasanagouda, T. & Adhikari, A. V. (2008). Acta Cryst. E64, o1263. Web of Science CSD CrossRef IUCr Journals Google Scholar
Tu, G. G., Li, S. H., Huang, H. M., Li, G., Xiong, F., Mai, X., Zhu, H. W., Kuang, B. H. & Xu, W. F. (2008). Bioorg. Med. Chem. 16, 6663–6668. Web of Science CrossRef PubMed CAS Google Scholar
Westrip, S. P. (2008). publCIF. In preparation. Google Scholar

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Volume 64| Part 10| October 2008| Page o2006

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

(2R)-N-[5-(4-Chloro­phen­yl)-1,3,4-thia­diazol-2-yl]-2-(cinnamoylamino)propanamide

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Footnotes

References

organic compounds

(2R)-N-[5-(4-Chlorophenyl)-1,3,4-thiadiazol-2-yl]-2-(cinnamoylamino)propanamide