(Z)-N-[3-(4-Bromo­benzo­yl)-1,3-thia­zolidin-2-yl­idene]cyanamide

Li, J.-M.; Yong, J.-P.; Huang, F.; Sun, L.; Xu, L.

doi:10.1107/S1600536810046520

organic compounds

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Volume 66| Part 12| December 2010| Page o3206

https://doi.org/10.1107/S1600536810046520

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(Z)-N-[3-(4-Bromobenzoyl)-1,3-thiazolidin-2-ylidene]cyanamide

Jiu-Ming Li,^a,^b ^* Jian-Ping Yong,^c Feng-lan Huang,^b,^d Li-mei Sun ^a,^b and Ling Xu ^a,^b

^aCollege of Chemistry and Chemical Engineering, Inner Mongolia University for Nationalities, Tongliao 028043, People's Republic of China, ^bInner Mongolia Industrial Engineering Research, Center of Universities for Castor, Tongliao 028042, People's Republic of China, ^cSchool of Public Health, Ningxia Medical University, Yinchuan 750004, People's Republic of China, and ^dCollege of Life Science, Inner Mongolia University for Nationalities, Tongliao 028043, People's Republic of China
^*Correspondence e-mail: lijiuming10@yahoo.cn

(Received 9 November 2010; accepted 10 November 2010; online 17 November 2010)

In the title compound, C₁₁H₈BrN₃OS, the dihedral angle between the benzene and thiazolidine rings is 63.4 (2)°. Intermolecular C—H⋯N interactions help to stabilize the crystal structure.

Related literature

For related structures, see: Wang et al. (2008 ); Liu & Li (2009 ); Xie & Li (2010 ). For the biological activity of thiazolidine-containing compounds, see: Iwata et al. (1988 ). For bond-length data, see: Allen et al. (1987 ).

Experimental

Crystal data

C₁₁H₈BrN₃OS
M_r = 310.17
Monoclinic, P 2₁ /c
a = 16.579 (3) Å
b = 5.6471 (11) Å
c = 13.611 (3) Å
β = 112.91 (3)°
V = 1173.9 (4) Å³
Z = 4
Mo Kα radiation
μ = 3.67 mm⁻¹
T = 173 K
0.25 × 0.20 × 0.06 mm

Data collection

Rigaku Mercury CCD/AFC diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2007 ) T_min = 0.461, T_max = 0.810
8232 measured reflections
2067 independent reflections
1960 reflections with I > 2σ(I)
R_int = 0.038

Refinement

R[F² > 2σ(F²)] = 0.037
wR(F²) = 0.108
S = 1.28
2067 reflections
154 parameters
H-atom parameters constrained
Δρ_max = 0.46 e Å⁻³
Δρ_min = −0.35 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C9—H9A⋯N3ⁱ	0.97	2.51	3.281 (5)	137
Symmetry code: (i) $[-x, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Data collection: CrystalClear (Rigaku, 2007); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536810046520/hg2746sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810046520/hg2746Isup2.hkl

checkCIF report

Comment top

Thiazolidine is an important kind of group in organic chemistry. Many compounds containing thiazolidine groups possess a broad spectrum of biological activities (Iwata et al., 1988). Here, we report the crystal structure of (I).

In title compound, all bond lengths in the molecular are normal (Allen et al., 1987) and in a good agreement with those reported previously (Wang et al., 2008; Liu & Li, 2009; Xie & Li, 2010). The dihedral angle between benzene (C1—C6) and thiazolidine (C8—C10/N1/S2) rings is 63.4 (2) °. The intermolecular C—H···N hydrogen bonds stabilize the structure.

Related literature top

For related structures, see: Wang et al. (2008); Liu & Li (2009); Xie & Li (2010). For the biological activity of thiazolidine-containing compounds, see: Iwata et al. (1988). For bond-length data, see: Allen et al. (1987).

Experimental top

A mixture of N-cyanoiminothiazolidine 10 mmol (1.27 g), 4-bromobenzoyl chloride (2.19 g, 10 mmol) and (1.01 g, 10 mmol) triethylamine was refluxed in absolute acetone (25 ml) for 3 h. On cooling, the product crystallized, was filtered, and recrystallized from absolute EtOH; yield 2.48 g (80.0%). Single crystals suitable for X-ray measurements were obtained by recrystallization from acetonitrile at room temperature.

Structure description top

For related structures, see: Wang et al. (2008); Liu & Li (2009); Xie & Li (2010). For the biological activity of thiazolidine-containing compounds, see: Iwata et al. (1988). For bond-length data, see: Allen et al. (1987).

Computing details top

Data collection: CrystalClear (Rigaku, 2007); cell refinement: CrystalClear (Rigaku, 2007); data reduction: CrystalClear (Rigaku, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of (I), with atom labels and 40% probability displacement ellipsoids for non-H atoms.

(Z)-N-[3-(4-Bromobenzoyl)-1,3-thiazolidin-2-ylidene]cyanamide top

Crystal data top

C₁₁H₈BrN₃OS	F(000) = 616
M_r = 310.17	D_x = 1.755 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3665 reflections
a = 16.579 (3) Å	θ = 1.3–27.5°
b = 5.6471 (11) Å	µ = 3.67 mm⁻¹
c = 13.611 (3) Å	T = 173 K
β = 112.91 (3)°	Plate, colorless
V = 1173.9 (4) Å³	0.25 × 0.20 × 0.06 mm
Z = 4

Data collection top

Rigaku Mercury CCD/AFC diffractometer	2067 independent reflections
Radiation source: Sealed Tube	1960 reflections with I > 2σ(I)
Graphite Monochromator monochromator	R_int = 0.038
φ and ω scans	θ_max = 25.0°, θ_min = 1.3°
Absorption correction: multi-scan (CrystalClear; Rigaku, 2007)	h = −17→19
T_min = 0.461, T_max = 0.810	k = −6→6
8232 measured reflections	l = −16→13

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.108	H-atom parameters constrained
S = 1.28	w = 1/[σ²(F_o²) + (0.054P)² + 0.437P] where P = (F_o² + 2F_c²)/3
2067 reflections	(Δ/σ)_max = 0.001
154 parameters	Δρ_max = 0.46 e Å⁻³
0 restraints	Δρ_min = −0.35 e Å⁻³

Crystal data top

C₁₁H₈BrN₃OS	V = 1173.9 (4) Å³
M_r = 310.17	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 16.579 (3) Å	µ = 3.67 mm⁻¹
b = 5.6471 (11) Å	T = 173 K
c = 13.611 (3) Å	0.25 × 0.20 × 0.06 mm
β = 112.91 (3)°

Data collection top

Rigaku Mercury CCD/AFC diffractometer	2067 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku, 2007)	1960 reflections with I > 2σ(I)
T_min = 0.461, T_max = 0.810	R_int = 0.038
8232 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	0 restraints
wR(F²) = 0.108	H-atom parameters constrained
S = 1.28	Δρ_max = 0.46 e Å⁻³
2067 reflections	Δρ_min = −0.35 e Å⁻³
154 parameters

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
Br1	0.46599 (2)	0.71386 (7)	0.56642 (3)	0.03845 (19)
S1	0.07775 (6)	0.52236 (16)	0.83336 (8)	0.0307 (2)
O1	0.26798 (18)	1.1823 (4)	0.8767 (2)	0.0362 (6)
N1	0.19890 (18)	0.8299 (5)	0.8536 (2)	0.0268 (6)
N2	0.15701 (19)	0.6055 (6)	0.6966 (2)	0.0316 (7)
N3	0.0788 (2)	0.2687 (6)	0.5834 (3)	0.0483 (10)
C1	0.3110 (2)	1.0740 (6)	0.6926 (3)	0.0281 (7)
H1A	0.2843	1.2215	0.6845	0.034*
C2	0.3582 (2)	1.0153 (6)	0.6309 (3)	0.0288 (8)
H2B	0.3614	1.1193	0.5796	0.035*
C3	0.3999 (2)	0.7995 (6)	0.6478 (3)	0.0267 (8)
C4	0.3960 (2)	0.6399 (6)	0.7235 (3)	0.0280 (8)
H4A	0.4261	0.4969	0.7347	0.034*
C5	0.3469 (2)	0.6969 (6)	0.7817 (3)	0.0274 (8)
H5A	0.3427	0.5903	0.8315	0.033*
C6	0.3036 (2)	0.9141 (6)	0.7661 (3)	0.0251 (7)
C7	0.2562 (2)	0.9906 (6)	0.8339 (3)	0.0276 (8)
C8	0.1669 (2)	0.8942 (7)	0.9375 (3)	0.0323 (8)
H8A	0.1231	1.0182	0.9126	0.039*
H8B	0.2148	0.9492	1.0011	0.039*
C9	0.1273 (2)	0.6690 (7)	0.9608 (3)	0.0332 (8)
H9A	0.0837	0.7059	0.9897	0.040*
H9B	0.1723	0.5702	1.0114	0.040*
C10	0.1498 (2)	0.6544 (6)	0.7864 (3)	0.0259 (7)
C11	0.1122 (2)	0.4235 (7)	0.6401 (3)	0.0339 (8)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.0425 (3)	0.0437 (3)	0.0358 (3)	−0.00069 (16)	0.0225 (2)	−0.00648 (16)
S1	0.0292 (5)	0.0296 (5)	0.0375 (5)	−0.0023 (4)	0.0175 (4)	0.0020 (4)
O1	0.0422 (15)	0.0270 (14)	0.0456 (17)	−0.0066 (11)	0.0239 (13)	−0.0086 (12)
N1	0.0302 (16)	0.0262 (15)	0.0266 (16)	−0.0027 (12)	0.0139 (13)	−0.0015 (12)
N2	0.0337 (16)	0.0340 (17)	0.0317 (16)	−0.0060 (13)	0.0178 (14)	−0.0028 (13)
N3	0.039 (2)	0.053 (2)	0.061 (3)	−0.0111 (17)	0.0277 (19)	−0.0232 (19)
C1	0.0256 (17)	0.0238 (17)	0.035 (2)	−0.0017 (14)	0.0117 (15)	0.0009 (15)
C2	0.0318 (18)	0.0275 (18)	0.0287 (19)	−0.0046 (14)	0.0135 (16)	0.0031 (14)
C3	0.0254 (18)	0.0306 (19)	0.0246 (19)	−0.0041 (14)	0.0103 (15)	−0.0045 (14)
C4	0.0283 (18)	0.0237 (17)	0.0308 (19)	−0.0007 (14)	0.0101 (15)	−0.0020 (14)
C5	0.0295 (19)	0.0231 (17)	0.0283 (19)	−0.0017 (14)	0.0097 (16)	0.0054 (14)
C6	0.0236 (16)	0.0248 (17)	0.0261 (18)	−0.0061 (14)	0.0088 (14)	−0.0043 (14)
C7	0.0258 (17)	0.0257 (18)	0.0324 (19)	−0.0002 (13)	0.0125 (15)	0.0017 (14)
C8	0.0360 (19)	0.036 (2)	0.030 (2)	−0.0016 (16)	0.0185 (16)	−0.0030 (16)
C9	0.0301 (19)	0.041 (2)	0.032 (2)	−0.0001 (16)	0.0158 (17)	0.0038 (17)
C10	0.0239 (17)	0.0228 (16)	0.0311 (19)	0.0013 (14)	0.0106 (15)	0.0031 (14)
C11	0.0310 (19)	0.035 (2)	0.043 (2)	−0.0043 (16)	0.0229 (17)	−0.0055 (18)

Geometric parameters (Å, º) top

Br1—C3	1.899 (4)	C2—C3	1.376 (5)
S1—C10	1.729 (3)	C2—H2B	0.9300
S1—C9	1.806 (4)	C3—C4	1.389 (5)
O1—C7	1.208 (4)	C4—C5	1.375 (5)
N1—C10	1.379 (4)	C4—H4A	0.9300
N1—C7	1.412 (4)	C5—C6	1.396 (5)
N1—C8	1.480 (4)	C5—H5A	0.9300
N2—C10	1.302 (5)	C6—C7	1.491 (5)
N2—C11	1.325 (5)	C8—C9	1.520 (5)
N3—C11	1.154 (5)	C8—H8A	0.9700
C1—C6	1.388 (5)	C8—H8B	0.9700
C1—C2	1.392 (5)	C9—H9A	0.9700
C1—H1A	0.9300	C9—H9B	0.9700

C10—S1—C9	92.05 (17)	C1—C6—C7	118.3 (3)
C10—N1—C7	127.0 (3)	C5—C6—C7	121.7 (3)
C10—N1—C8	113.1 (3)	O1—C7—N1	118.7 (3)
C7—N1—C8	117.3 (3)	O1—C7—C6	122.1 (3)
C10—N2—C11	118.3 (3)	N1—C7—C6	119.1 (3)
C6—C1—C2	120.5 (3)	N1—C8—C9	105.6 (3)
C6—C1—H1A	119.7	N1—C8—H8A	110.6
C2—C1—H1A	119.7	C9—C8—H8A	110.6
C3—C2—C1	118.3 (3)	N1—C8—H8B	110.6
C3—C2—H2B	120.8	C9—C8—H8B	110.6
C1—C2—H2B	120.8	H8A—C8—H8B	108.7
C2—C3—C4	122.2 (3)	C8—C9—S1	104.8 (3)
C2—C3—Br1	119.7 (3)	C8—C9—H9A	110.8
C4—C3—Br1	118.1 (3)	S1—C9—H9A	110.8
C5—C4—C3	118.9 (3)	C8—C9—H9B	110.8
C5—C4—H4A	120.5	S1—C9—H9B	110.8
C3—C4—H4A	120.5	H9A—C9—H9B	108.9
C4—C5—C6	120.2 (3)	N2—C10—N1	122.0 (3)
C4—C5—H5A	119.9	N2—C10—S1	125.7 (3)
C6—C5—H5A	119.9	N1—C10—S1	112.2 (2)
C1—C6—C5	119.8 (3)	N3—C11—N2	171.8 (4)

C6—C1—C2—C3	−2.6 (5)	C1—C6—C7—N1	138.8 (3)
C1—C2—C3—C4	0.3 (5)	C5—C6—C7—N1	−47.2 (4)
C1—C2—C3—Br1	−179.3 (2)	C10—N1—C8—C9	30.9 (4)
C2—C3—C4—C5	1.7 (5)	C7—N1—C8—C9	−165.9 (3)
Br1—C3—C4—C5	−178.7 (2)	N1—C8—C9—S1	−35.6 (3)
C3—C4—C5—C6	−1.4 (5)	C10—S1—C9—C8	26.6 (3)
C2—C1—C6—C5	2.9 (5)	C11—N2—C10—N1	175.3 (3)
C2—C1—C6—C7	177.0 (3)	C11—N2—C10—S1	−7.3 (5)
C4—C5—C6—C1	−0.8 (5)	C7—N1—C10—N2	5.6 (5)
C4—C5—C6—C7	−174.7 (3)	C8—N1—C10—N2	166.7 (3)
C10—N1—C7—O1	151.9 (3)	C7—N1—C10—S1	−172.1 (3)
C8—N1—C7—O1	−8.6 (5)	C8—N1—C10—S1	−11.0 (4)
C10—N1—C7—C6	−31.3 (5)	C9—S1—C10—N2	172.4 (3)
C8—N1—C7—C6	168.2 (3)	C9—S1—C10—N1	−10.0 (3)
C1—C6—C7—O1	−44.6 (5)	C10—N2—C11—N3	−171 (3)
C5—C6—C7—O1	129.4 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9A···N3ⁱ	0.97	2.51	3.281 (5)	137

Symmetry code: (i) −x, y+1/2, −z+3/2.

Experimental details

Crystal data
Chemical formula	C₁₁H₈BrN₃OS
M_r	310.17
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	173
a, b, c (Å)	16.579 (3), 5.6471 (11), 13.611 (3)
β (°)	112.91 (3)
V (Å³)	1173.9 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	3.67
Crystal size (mm)	0.25 × 0.20 × 0.06

Data collection
Diffractometer	Rigaku Mercury CCD/AFC
Absorption correction	Multi-scan (CrystalClear; Rigaku, 2007)
T_min, T_max	0.461, 0.810
No. of measured, independent and observed [I > 2σ(I)] reflections	8232, 2067, 1960
R_int	0.038
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.108, 1.28
No. of reflections	2067
No. of parameters	154
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.46, −0.35

Computer programs: CrystalClear (Rigaku, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9A···N3ⁱ	0.97	2.51	3.281 (5)	136.5

Symmetry code: (i) −x, y+1/2, −z+3/2.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CSD CrossRef Web of Science Google Scholar
Iwata, C., Watanabe, M., Okamoto, S., Fujimoto, M., Sakae, M., Katsurada, M. & Imanishi, T. (1988). Synthesis, 3, 261–262. Google Scholar
Liu, X.-L. & Li, Y.-M. (2009). Acta Cryst. E65, o1645. Web of Science CSD CrossRef IUCr Journals Google Scholar
Rigaku (2007). CrystalClear. Rigaku Corporation, Tokyo, Japan. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Wang, J.-G., Huang, L.-H. & Jian, F.-F. (2008). Acta Cryst. E64, o2321. Web of Science CSD CrossRef IUCr Journals Google Scholar
Xie, Y.-M. & Li, Y.-M. (2010). Acta Cryst. E66, o1158. Web of Science CSD CrossRef IUCr Journals Google Scholar

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CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 66| Part 12| December 2010| Page o3206

https://doi.org/10.1107/S1600536810046520

Open

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