3-[3-(2-Chloro-3,3,3-trifluoro­prop-1-en­yl)-2,2-dimethyl­cyclo­propane­carbon­yl]thia­zolidine-2-thione

Sun, N.-B.; Shen, D.-L.; Weng, J.-Q.; Tan, C.-X.

doi:10.1107/S1600536806031497

3-[3-(2-Chloro-3,3,3-trifluoroprop-1-enyl)-2,2-dimethylcyclopropanecarbonyl]thiazolidine-2-thione

N.-B. Sun, D.-L. Shen, J.-Q. Weng and C.-X. Tan

The title compound, C₁₂H₁₃ClF₃NOS₂, was prepared by a condensation reaction of 3-(2-chloro-3,3,3-trifluoroprop-1-enyl)-2,2-dimethylcyclopropanecarbonyl chloride and 1,3-thiazolidine-2-thione. In the crystal structure, the thiazolidine-2-thione group is in the thione form, although there may be tautomeric equilibrium with its thiol form in solution.

Read article Similar articles

Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806031497/ob2043sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536806031497/ob2043Isup2.hkl Contains datablock I

CCDC reference: 621449

checkCIF report

Key indicators

Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.003 Å
R factor = 0.044
wR factor = 0.117
Data-to-parameter ratio = 19.3

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT230_ALERT_2_B Hirshfeld Test Diff for    S2     -   C8      ..      14.46 su

Alert level C
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         S2
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         C8
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C7
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C11
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C12

   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
   5 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   6 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Computing details top

Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: CRYSTALS (Watkin et al., 1996); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: CrystalStructure.

3-[3-(2-Chloro-3,3,3-trifluoroprop-1-enyl)-2,2- dimethylcyclopropanecarbonyl]thiazolidine-2-thione top

Crystal data top

C₁₂H₁₃ClF₃NOS₂	F(000) = 704.00
M_r = 343.81	D_x = 1.489 Mg m⁻³
Monoclinic, P2₁/c	Melting point = 408–410 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71075 Å
a = 14.667 (8) Å	Cell parameters from 9919 reflections
b = 9.585 (4) Å	θ = 3.0–27.5°
c = 11.774 (5) Å	µ = 0.55 mm⁻¹
β = 112.131 (18)°	T = 298 K
V = 1533.2 (12) Å³	Needle, yellow
Z = 4	0.31 × 0.16 × 0.14 mm

Data collection top

Rigaku R-AXIS RAPID diffractometer	2015 reflections with F² > 2σ(F²)
Detector resolution: 10.00 pixels mm^-1	R_int = 0.040
ω scans	θ_max = 27.5°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −19→19
T_min = 0.835, T_max = 0.926	k = −12→12
14633 measured reflections	l = −14→15
3513 independent reflections

Refinement top

Refinement on F²	w = 4F_o²/[0.0005F_o² + σ(F_o²)]
R[F² > 2σ(F²)] = 0.044	(Δ/σ)_max < 0.001
wR(F²) = 0.117	Δρ_max = 0.43 e Å⁻³
S = 1.02	Δρ_min = −0.51 e Å⁻³
3513 reflections	Extinction correction: Larson (1970)
182 parameters	Extinction coefficient: 21 (2)
H-atom parameters constrained

Special details top

Geometry. ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY

Refinement. Refinement using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F². R-factor (gt) are based on F. The threshold expression of F² > 2.0 σ(F²) is used only for calculating R-factor (gt).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Cl1	0.37677 (6)	0.61033 (6)	0.34195 (6)	0.0785 (2)
S1	0.05822 (6)	−0.01116 (8)	0.29401 (8)	0.0964 (3)
S2	−0.11818 (6)	0.07841 (11)	0.32768 (9)	0.1109 (3)
F1	0.49305 (12)	0.70441 (19)	0.59700 (17)	0.1062 (6)
F2	0.34927 (14)	0.78218 (17)	0.54766 (19)	0.1161 (7)
F3	0.39927 (16)	0.62221 (17)	0.67960 (14)	0.1057 (6)
O1	0.16318 (13)	0.3475 (2)	0.54804 (17)	0.0923 (7)
N1	0.04108 (13)	0.21776 (19)	0.42147 (16)	0.0560 (5)
C1	0.28766 (16)	0.3301 (2)	0.39907 (17)	0.0472 (5)
C2	0.29436 (17)	0.1784 (2)	0.43439 (17)	0.0510 (6)
C3	0.19440 (17)	0.2470 (2)	0.38189 (18)	0.0504 (6)
C4	0.3372 (2)	0.1377 (2)	0.5685 (2)	0.0732 (8)
C5	0.3183 (2)	0.0762 (2)	0.3514 (2)	0.0650 (7)
C6	0.13658 (18)	0.2747 (2)	0.4578 (2)	0.0580 (6)
C7	0.0036 (2)	0.1026 (2)	0.3498 (2)	0.0677 (7)
C8	−0.1268 (2)	0.2363 (3)	0.4010 (3)	0.1107 (13)
C9	−0.0220 (2)	0.2746 (2)	0.4824 (2)	0.0771 (9)
C10	0.32552 (16)	0.4408 (2)	0.49028 (18)	0.0470 (5)
C11	0.36472 (14)	0.5597 (2)	0.47615 (18)	0.0472 (5)
C12	0.4020 (2)	0.6659 (2)	0.5750 (2)	0.0647 (7)
H1	0.2976	0.3477	0.3225	0.057*
H3	0.1552	0.2215	0.2968	0.060*
H10	0.3214	0.4255	0.5662	0.056*
H41	0.3127	0.0476	0.5786	0.088*
H42	0.4077	0.1343	0.5961	0.088*
H43	0.3184	0.2054	0.6157	0.088*
H51	0.3881	0.0749	0.3715	0.078*
H52	0.2854	0.1044	0.2675	0.078*
H53	0.2964	−0.0154	0.3624	0.078*
H81	−0.1557	0.3089	0.3407	0.133*
H82	−0.1665	0.2232	0.4500	0.133*
H91	−0.0048	0.2334	0.5630	0.093*
H92	−0.0148	0.3751	0.4901	0.093*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0898 (5)	0.0775 (4)	0.0719 (4)	−0.0194 (3)	0.0347 (3)	0.0176 (3)
S1	0.1245 (7)	0.0799 (5)	0.1037 (5)	−0.0475 (4)	0.0644 (5)	−0.0402 (4)
S2	0.0671 (5)	0.1329 (8)	0.1255 (7)	−0.0446 (5)	0.0281 (4)	−0.0222 (5)
F1	0.0732 (11)	0.1080 (12)	0.1418 (14)	−0.0416 (9)	0.0457 (10)	−0.0517 (11)
F2	0.1276 (16)	0.0564 (9)	0.1673 (17)	0.0176 (9)	0.0590 (13)	−0.0151 (10)
F3	0.1633 (18)	0.0840 (10)	0.0850 (10)	−0.0486 (11)	0.0638 (11)	−0.0345 (8)
O1	0.0812 (13)	0.1231 (15)	0.0905 (12)	−0.0483 (11)	0.0528 (10)	−0.0578 (11)
N1	0.0519 (12)	0.0561 (10)	0.0619 (10)	−0.0118 (9)	0.0235 (9)	−0.0004 (8)
C1	0.0518 (13)	0.0508 (11)	0.0410 (9)	−0.0088 (9)	0.0197 (8)	0.0009 (8)
C2	0.0630 (15)	0.0470 (11)	0.0439 (10)	−0.0050 (10)	0.0211 (10)	−0.0017 (9)
C3	0.0535 (13)	0.0555 (12)	0.0412 (10)	−0.0130 (10)	0.0168 (9)	−0.0058 (9)
C4	0.102 (2)	0.0583 (14)	0.0526 (12)	0.0018 (13)	0.0217 (13)	0.0034 (10)
C5	0.0779 (18)	0.0544 (13)	0.0646 (13)	−0.0015 (12)	0.0291 (12)	−0.0086 (11)
C6	0.0573 (15)	0.0609 (13)	0.0584 (12)	−0.0153 (11)	0.0249 (11)	−0.0113 (11)
C7	0.0694 (17)	0.0714 (15)	0.0574 (12)	−0.0276 (13)	0.0184 (11)	0.0006 (11)
C8	0.054 (2)	0.129 (2)	0.152 (2)	−0.0017 (18)	0.0421 (19)	0.031 (2)
C9	0.0678 (19)	0.0731 (16)	0.1044 (19)	−0.0079 (13)	0.0483 (16)	−0.0048 (14)
C10	0.0511 (13)	0.0456 (11)	0.0477 (10)	−0.0034 (9)	0.0224 (9)	−0.0003 (9)
C11	0.0409 (12)	0.0463 (11)	0.0557 (11)	0.0017 (9)	0.0195 (9)	0.0047 (9)
C12	0.0630 (17)	0.0457 (12)	0.0907 (17)	−0.0096 (11)	0.0351 (13)	−0.0073 (12)

Geometric parameters (Å, º) top

Cl1—C11	1.724 (2)	C3—C6	1.470 (3)
S1—C7	1.631 (3)	C8—C9	1.518 (3)
S2—C7	1.721 (3)	C10—C11	1.315 (3)
S2—C8	1.770 (4)	C11—C12	1.487 (3)
F1—C12	1.314 (3)	C1—H1	0.980
F2—C12	1.325 (2)	C3—H3	0.980
F3—C12	1.315 (3)	C4—H41	0.960
O1—C6	1.206 (2)	C4—H42	0.960
N1—C6	1.411 (3)	C4—H43	0.960
N1—C7	1.372 (2)	C5—H51	0.960
N1—C9	1.472 (4)	C5—H52	0.960
C1—C2	1.505 (2)	C5—H53	0.960
C1—C3	1.529 (3)	C8—H81	0.970
C1—C10	1.462 (2)	C8—H82	0.970
C2—C3	1.510 (3)	C9—H91	0.970
C2—C4	1.514 (2)	C9—H92	0.970
C2—C5	1.515 (3)	C10—H10	0.930

C7—S2—C8	94.12 (14)	F2—C12—C11	112.15 (19)
C6—N1—C7	128.3 (2)	F3—C12—C11	112.5 (2)
C6—N1—C9	116.33 (18)	C2—C1—H1	113.8
C7—N1—C9	114.7 (2)	C3—C1—H1	113.8
C2—C1—C3	59.70 (14)	C10—C1—H1	113.8
C2—C1—C10	122.06 (15)	C1—C3—H3	114.6
C3—C1—C10	123.3 (2)	C2—C3—H3	114.6
C1—C2—C3	60.95 (14)	C6—C3—H3	114.6
C1—C2—C4	119.69 (16)	C2—C4—H41	109.5
C1—C2—C5	116.94 (19)	C2—C4—H42	109.5
C3—C2—C4	119.8 (2)	C2—C4—H43	109.5
C3—C2—C5	116.23 (16)	H41—C4—H42	109.5
C4—C2—C5	113.58 (18)	H41—C4—H43	109.5
C1—C3—C2	59.35 (14)	H42—C4—H43	109.5
C1—C3—C6	121.18 (17)	C2—C5—H51	109.5
C2—C3—C6	121.56 (17)	C2—C5—H52	109.5
O1—C6—N1	116.4 (2)	C2—C5—H53	109.5
O1—C6—C3	124.8 (2)	H51—C5—H52	109.5
N1—C6—C3	118.68 (18)	H51—C5—H53	109.5
S1—C7—S2	119.24 (14)	H52—C5—H53	109.5
S1—C7—N1	129.9 (2)	S2—C8—H81	110.4
S2—C7—N1	110.7 (2)	S2—C8—H82	110.4
S2—C8—C9	105.8 (2)	C9—C8—H81	110.4
N1—C9—C8	106.0 (2)	C9—C8—H82	110.4
C1—C10—C11	126.8 (2)	H81—C8—H82	109.5
Cl1—C11—C10	124.10 (16)	N1—C9—H91	110.3
Cl1—C11—C12	112.97 (17)	N1—C9—H92	110.3
C10—C11—C12	122.9 (2)	C8—C9—H91	110.3
F1—C12—F2	105.5 (2)	C8—C9—H92	110.3
F1—C12—F3	107.0 (2)	H91—C9—H92	109.5
F1—C12—C11	113.1 (2)	C1—C10—H10	116.6
F2—C12—F3	106.0 (2)	C11—C10—H10	116.6

C7—S2—C8—C9	−21.3 (2)	C10—C1—C3—C2	−110.6 (2)
C8—S2—C7—S1	−177.10 (18)	C10—C1—C3—C6	0.0 (2)
C8—S2—C7—N1	6.3 (2)	C1—C2—C3—C6	−110.0 (2)
C6—N1—C7—S1	5.7 (3)	C4—C2—C3—C1	109.6 (2)
C6—N1—C7—S2	−178.17 (17)	C4—C2—C3—C6	−0.4 (2)
C7—N1—C6—O1	−158.2 (2)	C5—C2—C3—C1	−107.7 (2)
C7—N1—C6—C3	24.4 (3)	C5—C2—C3—C6	142.3 (2)
C6—N1—C9—C8	161.2 (2)	C1—C3—C6—O1	−10.9 (3)
C9—N1—C6—O1	11.5 (2)	C1—C3—C6—N1	166.36 (17)
C9—N1—C6—C3	−166.00 (19)	C2—C3—C6—O1	60.0 (3)
C7—N1—C9—C8	−27.7 (2)	C2—C3—C6—N1	−122.8 (2)
C9—N1—C7—S1	−164.1 (2)	S2—C8—C9—N1	29.8 (2)
C9—N1—C7—S2	12.1 (2)	C1—C10—C11—Cl1	1.5 (3)
C2—C1—C3—C6	110.6 (2)	C1—C10—C11—C12	−179.6 (2)
C3—C1—C2—C4	−109.7 (2)	Cl1—C11—C12—F1	−53.9 (2)
C3—C1—C2—C5	106.6 (2)	Cl1—C11—C12—F2	65.4 (2)
C2—C1—C10—C11	146.8 (2)	Cl1—C11—C12—F3	−175.24 (18)
C10—C1—C2—C3	112.6 (2)	C10—C11—C12—F1	127.1 (2)
C10—C1—C2—C4	2.8 (3)	C10—C11—C12—F2	−113.7 (2)
C10—C1—C2—C5	−140.9 (2)	C10—C11—C12—F3	5.7 (3)
C3—C1—C10—C11	−140.7 (2)

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Text
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Text
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

3-[3-(2-Chloro-3,3,3-trifluoro­prop-1-en­yl)-2,2-dimethyl­cyclo­propane­carbon­yl]thia­zolidine-2-thione

Supporting information

Key indicators

checkCIF/PLATON results

3-[3-(2-Chloro-3,3,3-trifluoroprop-1-enyl)-2,2-dimethylcyclopropanecarbonyl]thiazolidine-2-thione