Literature DB >> 22259506

N-(5-Sulfanyl-idene-4,5-dihydro-1,3,4-thia-diazol-2-yl)acetamide dimethyl sulfoxide disolvate.

Sung Kwon Kang¹, Nam Sook Cho, Siyoung Jang.

Abstract

In the title compound, C(4)H(5)N(3)OS(2)·2C(2)H(6)OS, the five-membered heterocyclic ring and the N-(C=O)-C plane of the acetamide group are essentially co-planar, with a dihedral angle of 1.25 (3)°. Inter-molecular N-H⋯O hydrogen bonds between the acetamide compound and the dimethyl sulfoxide mol-ecules stabilize the crystal structure. The two dimethyl sulfoxide mol-ecules are each disordered over two positions with occupancy ratios of 0.605 (2):0.395 (2) and 0.8629 (18):0.1371 (18).

Entities: CellLine Chemical Disease Species

Year: 2011 PMID： 22259506 PMCID： PMC3254557 DOI： 10.1107/S1600536811054298

Source DB: PubMed Journal: Acta Crystallogr Sect E Struct Rep Online ISSN： 1600-5368

Related literature

For the synthesis and biological activity of thiadiazole compounds, see: Hildebrandt et al. (2011 ▶); Cho et al. (1993 ▶). For the structures of thiadiazole derivatives, see: Zhan et al. (2007 ▶, 2009 ▶).

Experimental

Crystal data

C4H5N3OS2·2C2H6OS M = 331.49 Triclinic, a = 7.090 (2) Å b = 9.982 (3) Å c = 11.513 (3) Å α = 100.872 (6)° β = 96.827 (4)° γ = 91.359 (4)° V = 793.6 (4) Å3 Z = 2 Mo Kα radiation μ = 0.60 mm−1 T = 296 K 0.28 × 0.18 × 0.13 mm

Data collection

Bruker SMART CCD area-detector diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2002 ▶) T min = 0.894, T max = 0.916 24389 measured reflections 3292 independent reflections 2625 reflections with I > 2σ(I) R int = 0.180

Refinement

R[F 2 > 2σ(F 2)] = 0.039 wR(F 2) = 0.117 S = 1.06 3292 reflections 245 parameters 7 restraints H atoms treated by a mixture of independent and constrained refinement Δρmax = 0.22 e Å−3 Δρmin = −0.35 e Å−3 Data collection: SMART (Bruker, 2002 ▶); cell refinement: SAINT (Bruker, 2002 ▶); 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 (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶). Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811054298/is5026sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811054298/is5026Isup2.hkl Supplementary material file. DOI: 10.1107/S1600536811054298/is5026Isup3.cml Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C₄H₅N₃OS₂·2C₂H₆OS	Z = 2
M_r = 331.49	F(000) = 348
Triclinic, P1	D_x = 1.387 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.090 (2) Å	Cell parameters from 8583 reflections
b = 9.982 (3) Å	θ = 2.5–27.9°
c = 11.513 (3) Å	µ = 0.60 mm⁻¹
α = 100.872 (6)°	T = 296 K
β = 96.827 (4)°	Block, colourless
γ = 91.359 (4)°	0.28 × 0.18 × 0.13 mm
V = 793.6 (4) Å³

Bruker SMART CCD area-detector diffractometer	2625 reflections with I > 2σ(I)
graphite	R_int = 0.180
φ and ω scans	θ_max = 26.5°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2002)	h = −8→8
T_min = 0.894, T_max = 0.916	k = −12→12
24389 measured reflections	l = −14→14
3292 independent 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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.117	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ²(F_o²) + (0.0538P)² + 0.016P] where P = (F_o² + 2F_c²)/3
3292 reflections	(Δ/σ)_max < 0.001
245 parameters	Δρ_max = 0.22 e Å⁻³
7 restraints	Δρ_min = −0.35 e Å⁻³

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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	U_iso*/U_eq	Occ. (<1)
C1	0.2794 (2)	0.12725 (17)	0.77693 (18)	0.0551 (4)
S2	0.26666 (7)	0.02071 (4)	0.63771 (4)	0.05621 (17)
C3	0.2555 (2)	0.16373 (16)	0.57197 (17)	0.0504 (4)
N4	0.2592 (2)	0.27936 (14)	0.64572 (16)	0.0618 (4)
N5	0.2732 (2)	0.25591 (15)	0.75980 (16)	0.0604 (4)
H5	0.277 (4)	0.323 (2)	0.822 (2)	0.113 (10)*
S6	0.29892 (10)	0.07416 (6)	0.90641 (5)	0.0767 (2)
N7	0.2429 (2)	0.15853 (15)	0.45173 (15)	0.0566 (4)
H7	0.238 (3)	0.237 (2)	0.432 (2)	0.070 (6)*
C8	0.2374 (3)	0.03883 (18)	0.36972 (18)	0.0577 (5)
C9	0.2250 (3)	0.0526 (2)	0.2426 (2)	0.0721 (6)
H9A	0.2405	0.1472	0.2382	0.108*
H9B	0.103	0.0168	0.2017	0.108*
H9C	0.3234	0.0026	0.2058	0.108*
O10	0.2408 (2)	−0.07095 (13)	0.40190 (14)	0.0768 (4)
S11	0.14717 (14)	0.51941 (8)	0.37275 (8)	0.0627 (4)	0.605 (2)
O12	0.2642 (8)	0.3906 (8)	0.3592 (8)	0.0824 (17)	0.605 (2)
C13	0.265 (2)	0.6272 (13)	0.5029 (11)	0.101 (4)	0.605 (2)
H13A	0.2399	0.5925	0.5721	0.151*	0.605 (2)
H13B	0.2205	0.7179	0.5081	0.151*	0.605 (2)
H13C	0.4	0.6296	0.4989	0.151*	0.605 (2)
C14	0.2160 (13)	0.6060 (7)	0.2625 (7)	0.068 (3)	0.605 (2)
H14A	0.1725	0.5532	0.1848	0.102*	0.605 (2)
H14B	0.352	0.6181	0.2719	0.102*	0.605 (2)
H14C	0.1607	0.6936	0.271	0.102*	0.605 (2)
S11A	0.3122 (2)	0.52142 (13)	0.37732 (12)	0.0645 (5)	0.395 (2)
O12A	0.1799 (11)	0.3913 (11)	0.3575 (12)	0.076 (2)	0.395 (2)
C13A	0.231 (3)	0.6329 (17)	0.4958 (14)	0.080 (4)	0.395 (2)
H13D	0.2722	0.6043	0.5693	0.12*	0.395 (2)
H13E	0.0943	0.6316	0.4838	0.12*	0.395 (2)
H13F	0.2811	0.7239	0.499	0.12*	0.395 (2)
C14A	0.220 (3)	0.6115 (17)	0.2720 (14)	0.114 (7)	0.395 (2)
H14D	0.2269	0.5592	0.1938	0.171*	0.395 (2)
H14E	0.2912	0.6967	0.2821	0.171*	0.395 (2)
H14F	0.0893	0.6289	0.2815	0.171*	0.395 (2)
S15	0.30211 (9)	0.63050 (5)	0.96900 (5)	0.0570 (2)	0.8629 (18)
O16	0.2521 (8)	0.4816 (3)	0.9404 (3)	0.0775 (9)	0.8629 (18)
C17	0.0886 (7)	0.7112 (4)	0.9385 (3)	0.0873 (8)	0.8629 (18)
H17A	0.0047	0.6992	0.9957	0.131*	0.8629 (18)
H17B	0.029	0.6716	0.8598	0.131*	0.8629 (18)
H17C	0.1156	0.807	0.9433	0.131*	0.8629 (18)
C18	0.4168 (7)	0.6718 (6)	0.8504 (5)	0.096 (2)	0.8629 (18)
H18A	0.5394	0.6329	0.8514	0.144*	0.8629 (18)
H18B	0.432	0.7692	0.8598	0.144*	0.8629 (18)
H18C	0.341	0.6355	0.7758	0.144*	0.8629 (18)
S15A	0.2077 (7)	0.6133 (4)	0.8695 (4)	0.0785 (16)	0.1371 (18)
O16A	0.235 (6)	0.4742 (18)	0.8952 (17)	0.085 (7)	0.1371 (18)
C17A	0.136 (4)	0.735 (3)	0.9939 (13)	0.084 (9)	0.1371 (18)
H17D	0.0093	0.7106	1.0059	0.126*	0.1371 (18)
H17E	0.141	0.8248	0.9765	0.126*	0.1371 (18)
H17F	0.2215	0.732	1.0647	0.126*	0.1371 (18)
C18A	0.444 (3)	0.679 (2)	0.876 (3)	0.074 (9)	0.1371 (18)
H18D	0.5276	0.6042	0.8642	0.111*	0.1371 (18)
H18E	0.4821	0.7358	0.9524	0.111*	0.1371 (18)
H18F	0.4509	0.7311	0.8146	0.111*	0.1371 (18)

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0548 (10)	0.0387 (8)	0.0736 (12)	0.0039 (7)	0.0097 (8)	0.0141 (8)
S2	0.0670 (3)	0.0319 (2)	0.0721 (3)	0.00558 (19)	0.0085 (2)	0.0157 (2)
C3	0.0503 (9)	0.0337 (8)	0.0705 (12)	0.0047 (7)	0.0102 (8)	0.0162 (7)
N4	0.0803 (11)	0.0341 (7)	0.0735 (11)	0.0070 (7)	0.0120 (8)	0.0148 (7)
N5	0.0752 (10)	0.0376 (8)	0.0700 (11)	0.0056 (7)	0.0123 (8)	0.0125 (7)
S6	0.1065 (5)	0.0548 (3)	0.0725 (4)	0.0054 (3)	0.0090 (3)	0.0227 (3)
N7	0.0644 (9)	0.0363 (7)	0.0729 (11)	0.0053 (6)	0.0091 (7)	0.0196 (7)
C8	0.0561 (10)	0.0457 (9)	0.0719 (12)	0.0033 (8)	0.0072 (9)	0.0132 (8)
C9	0.0815 (14)	0.0619 (12)	0.0734 (14)	0.0056 (10)	0.0078 (11)	0.0155 (10)
O10	0.1132 (12)	0.0372 (7)	0.0806 (10)	0.0058 (7)	0.0118 (9)	0.0129 (6)
S11	0.0750 (8)	0.0494 (5)	0.0673 (6)	−0.0013 (4)	0.0127 (4)	0.0184 (4)
O12	0.120 (4)	0.0437 (17)	0.093 (3)	0.019 (3)	0.030 (4)	0.0259 (16)
C13	0.151 (8)	0.073 (6)	0.066 (5)	0.012 (4)	−0.019 (4)	0.000 (4)
C14	0.116 (6)	0.040 (3)	0.057 (4)	−0.003 (3)	0.007 (3)	0.032 (3)
S11A	0.0768 (12)	0.0559 (8)	0.0666 (8)	0.0172 (6)	0.0152 (6)	0.0216 (6)
O12A	0.115 (6)	0.036 (2)	0.079 (4)	0.008 (4)	0.003 (5)	0.020 (2)
C13A	0.123 (9)	0.061 (7)	0.064 (8)	0.008 (5)	0.031 (7)	0.020 (5)
C14A	0.151 (16)	0.097 (9)	0.089 (10)	0.037 (8)	0.025 (9)	−0.004 (7)
S15	0.0831 (4)	0.0407 (3)	0.0477 (4)	0.0060 (2)	0.0121 (3)	0.0067 (2)
O16	0.117 (2)	0.0372 (13)	0.080 (2)	0.0071 (13)	0.026 (2)	0.0065 (14)
C17	0.096 (2)	0.0585 (18)	0.11	0.0158 (16)	0.019 (3)	0.019 (2)
C18	0.126 (4)	0.093 (3)	0.073 (3)	−0.013 (3)	0.045 (3)	0.012 (2)
S15A	0.106 (3)	0.056 (2)	0.068 (3)	0.000 (2)	−0.002 (2)	0.0071 (18)
O16A	0.159 (16)	0.023 (6)	0.064 (13)	−0.004 (7)	0.029 (14)	−0.021 (7)
C17A	0.15 (3)	0.077 (14)	0.039 (8)	0.048 (15)	0.054 (13)	0.010 (10)
C18A	0.103 (16)	0.034 (9)	0.067 (15)	0.016 (9)	−0.030 (12)	−0.013 (8)

C1—N5	1.337 (2)	S11A—C13A	1.754 (15)
C1—S6	1.666 (2)	C13A—H13D	0.96
C1—S2	1.740 (2)	C13A—H13E	0.96
S2—C3	1.7367 (17)	C13A—H13F	0.96
C3—N4	1.295 (2)	C14A—H14D	0.96
C3—N7	1.368 (2)	C14A—H14E	0.96
N4—N5	1.370 (2)	C14A—H14F	0.96
N5—H5	0.878 (17)	S15—O16	1.486 (4)
N7—C8	1.373 (2)	S15—C17	1.762 (4)
N7—H7	0.86 (2)	S15—C18	1.777 (5)
C8—O10	1.221 (2)	C17—H17A	0.96
C8—C9	1.488 (3)	C17—H17B	0.96
C9—H9A	0.96	C17—H17C	0.96
C9—H9B	0.96	C18—H18A	0.96
C9—H9C	0.96	C18—H18B	0.96
S11—O12	1.540 (7)	C18—H18C	0.96
S11—C14	1.772 (5)	S15A—O16A	1.485 (18)
S11—C13	1.777 (12)	S15A—C18A	1.772 (19)
C13—H13A	0.96	S15A—C17A	1.822 (14)
C13—H13B	0.96	C17A—H17D	0.96
C13—H13C	0.96	C17A—H17E	0.96
C14—H14A	0.96	C17A—H17F	0.96
C14—H14B	0.96	C18A—H18D	0.96
C14—H14C	0.96	C18A—H18E	0.96
S11A—O12A	1.548 (11)	C18A—H18F	0.96
S11A—C14A	1.720 (12)

N5—C1—S6	127.50 (16)	S11A—C13A—H13E	109.5
N5—C1—S2	107.67 (15)	H13D—C13A—H13E	109.5
S6—C1—S2	124.82 (10)	S11A—C13A—H13F	109.5
C3—S2—C1	89.24 (9)	H13D—C13A—H13F	109.5
N4—C3—N7	121.00 (16)	H13E—C13A—H13F	109.5
N4—C3—S2	115.01 (15)	S11A—C14A—H14D	109.5
N7—C3—S2	124.00 (13)	S11A—C14A—H14E	109.5
C3—N4—N5	109.17 (14)	H14D—C14A—H14E	109.5
C1—N5—N4	118.91 (17)	S11A—C14A—H14F	109.5
C1—N5—H5	119 (2)	H14D—C14A—H14F	109.5
N4—N5—H5	121.9 (19)	H14E—C14A—H14F	109.5
C3—N7—C8	123.36 (16)	O16—S15—C17	105.9 (3)
C3—N7—H7	113.9 (15)	O16—S15—C18	107.7 (3)
C8—N7—H7	122.7 (15)	C17—S15—C18	97.3 (3)
O10—C8—N7	120.52 (19)	S15—C17—H17A	109.5
O10—C8—C9	123.44 (18)	S15—C17—H17B	109.5
N7—C8—C9	116.04 (17)	H17A—C17—H17B	109.5
C8—C9—H9A	109.5	S15—C17—H17C	109.5
C8—C9—H9B	109.5	H17A—C17—H17C	109.5
H9A—C9—H9B	109.5	H17B—C17—H17C	109.5
C8—C9—H9C	109.5	S15—C18—H18A	109.5
H9A—C9—H9C	109.5	S15—C18—H18B	109.5
H9B—C9—H9C	109.5	H18A—C18—H18B	109.5
O12—S11—C14	104.0 (4)	S15—C18—H18C	109.5
O12—S11—C13	103.8 (6)	H18A—C18—H18C	109.5
C14—S11—C13	99.9 (5)	H18B—C18—H18C	109.5
S11—C13—H13A	109.5	O16A—S15A—C18A	102.8 (19)
S11—C13—H13B	109.5	O16A—S15A—C17A	113.6 (12)
H13A—C13—H13B	109.5	C18A—S15A—C17A	98.3 (14)
S11—C13—H13C	109.5	S15A—C17A—H17D	109.5
H13A—C13—H13C	109.5	S15A—C17A—H17E	109.5
H13B—C13—H13C	109.5	H17D—C17A—H17E	109.5
S11—C14—H14A	109.5	S15A—C17A—H17F	109.5
S11—C14—H14B	109.5	H17D—C17A—H17F	109.5
H14A—C14—H14B	109.5	H17E—C17A—H17F	109.5
S11—C14—H14C	109.5	S15A—C18A—H18D	109.5
H14A—C14—H14C	109.5	S15A—C18A—H18E	109.5
H14B—C14—H14C	109.5	H18D—C18A—H18E	109.5
O12A—S11A—C14A	104.9 (8)	S15A—C18A—H18F	109.5
O12A—S11A—C13A	104.7 (7)	H18D—C18A—H18F	109.5
C14A—S11A—C13A	93.7 (9)	H18E—C18A—H18F	109.5
S11A—C13A—H13D	109.5

D—H···A	D—H	H···A	D···A	D—H···A
N5—H5···O16	0.88 (2)	1.91 (2)	2.783 (3)	170 (3)
N7—H7···O12	0.86 (2)	1.89 (2)	2.734 (8)	166 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N5—H5⋯O16	0.88 (2)	1.91 (2)	2.783 (3)	170 (3)
N7—H7⋯O12	0.86 (2)	1.89 (2)	2.734 (8)	166 (2)

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Authors: George M Sheldrick
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