2,2′-Bi-1,3-thia­zolidine

The title compound, C₆H₁₂N₂S₂, possesses a centre of symmetry with one-half of the mol­ecule in the asymmetric unit. The crystal structure has inter­molecular N—H...N and C—H...S contacts and intra­molecular S...N inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.036
• wR factor = 0.091
• Data-to-parameter ratio = 12.5

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT022_ALERT_3_C Ratio Unique / Expected Reflections too Low ....       0.93
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.97
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.14
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature        293 K

Alert level G
REFLT03_ALERT_1_G ALERT: Expected hkl max differ from CIF values
           From the CIF: _diffrn_reflns_theta_max           27.45
           From the CIF: _reflns_number_total                878
           From the CIF: _diffrn_reflns_limit_ max hkl   10.    4.   12.
           From the CIF: _diffrn_reflns_limit_ min hkl  -10.   -6.  -12.
           TEST1: Expected hkl limits for theta max
           Calculated maximum hkl   12.    6.   12.
           Calculated minimum hkl  -12.   -6.  -12.

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

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


checkCIF publication errors

Alert level A
PUBL024_ALERT_1_A The number of authors is greater than 5.
              Please specify the role of each of the co-authors
              for your paper.

Author Response: Professors Yliana Yliana L\'opez and M. Eugenia Ochoa are the ones in charge of the synthesis and characterization of the compound. Professors Rosa Santillan and Norberto Farf\'an are the ones in charge of the research project. Professors Itzia I. Padilla-Mart\'inez and Efr\'en V. Garc\'ia-B\'aez are the ones in charge of the analysis of the crystal.

   1 ALERT level A = Data missing that is essential or data in wrong format
   0 ALERT level G = General alerts. Data that may be required is missing

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Computing details

Data collection: COLLECT (Nonius, 2000); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: SCALEPACK and DENZO (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97(Sheldrick 1990); program(s) used to refine structure: SHELXL97 (Sheldrick 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: WinGX (Farrugia, 1999).

2,2'-Bi-1,3-thiazolidine

Crystal data

C6H12N2S2	F(000) = 188
Mr = 176.30	Dx = 1.415 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 600 reflections
a = 9.4931 (6) Å	θ = 20–25°
b = 5.0070 (4) Å	µ = 0.57 mm^−1
c = 9.5942 (8) Å	T = 293 K
β = 114.844 (3)°	Block, colorless
V = 413.83 (6) Å^3	0.15 × 0.10 × 0.08 mm
Z = 2

Data collection

Nonius KappaCCD diffractometer	785 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.019
Graphite monochromator	θmax = 27.5°, θmin = 4.7°
Detector resolution: 9 pixels mm^-1	h = −10→10
φ and ω scans	k = −6→4
1332 measured reflections	l = −12→12
878 independent reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.091	All H-atom parameters refined
S = 1.07	w = 1/[σ^2(Fo^2) + (0.0315P)^2 + 0.2832P] where P = (Fo^2 + 2Fc^2)/3
878 reflections	(Δ/σ)max < 0.001
70 parameters	Δρmax = 0.62 e Å^−3
0 restraints	Δρmin = −0.29 e Å^−3

Special details

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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 (Ų)

	x	y	z	Uiso*/Ueq
S1	−0.14926 (5)	0.70330 (12)	0.09502 (5)	0.0396 (2)
N3	0.13613 (18)	0.4867 (4)	0.20915 (17)	0.0341 (5)
C2	0.0254 (2)	0.6007 (4)	0.0652 (2)	0.0321 (5)
C4	0.0551 (3)	0.3845 (5)	0.2986 (2)	0.0393 (6)
C5	−0.0647 (3)	0.5918 (5)	0.2931 (2)	0.0416 (7)
H2	0.074 (3)	0.767 (5)	0.032 (3)	0.040 (6)*
H3	0.200 (3)	0.616 (6)	0.263 (3)	0.052 (7)*
H4A	0.003 (3)	0.219 (6)	0.248 (3)	0.052 (7)*
H4B	0.127 (3)	0.348 (5)	0.399 (3)	0.044 (7)*
H5A	−0.014 (4)	0.748 (6)	0.360 (4)	0.063 (8)*
H5B	−0.143 (3)	0.520 (6)	0.319 (3)	0.059 (8)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0326 (3)	0.0513 (4)	0.0326 (3)	0.0101 (2)	0.0116 (2)	−0.0016 (2)
N3	0.0297 (8)	0.0434 (10)	0.0240 (8)	0.0024 (7)	0.0061 (6)	−0.0001 (7)
C2	0.0294 (9)	0.0355 (10)	0.0282 (9)	0.0017 (8)	0.0089 (7)	0.0002 (8)
C4	0.0413 (11)	0.0402 (12)	0.0309 (10)	−0.0050 (9)	0.0099 (8)	0.0034 (9)
C5	0.0400 (11)	0.0539 (14)	0.0338 (10)	−0.0036 (10)	0.0185 (8)	0.0001 (9)

Geometric parameters (Å, º)

S1—C2	1.869 (2)	C4—C5	1.524 (4)
S1—C5	1.8127 (19)	C2—H2	1.06 (3)
N3—C2	1.455 (2)	C4—H4A	0.98 (3)
N3—C4	1.465 (3)	C4—H4B	0.94 (3)
N3—H3	0.89 (3)	C5—H5A	1.00 (3)
C2—C2^i	1.519 (3)	C5—H5B	0.95 (3)
S1···C4^ii	3.677 (2)	C4···H3^vi	2.95 (3)
S1···N3^i	3.1213 (17)	C4···H2^i	2.98 (3)
S1···H4A^iii	3.02 (3)	H2···S1^iv	3.12 (3)
S1···H2^iv	3.12 (3)	H2···C4^i	2.98 (3)
S1···H5B^v	2.91 (3)	H2···H4A^i	2.47 (4)
S1···H3^ii	3.03 (3)	H3···N3^vii	2.36 (3)
S1···H4B^ii	3.12 (3)	H3···C4^vii	2.95 (3)
N3···N3^vi	3.183 (3)	H3···S1^viii	3.03 (3)
N3···N3^vii	3.183 (3)	H4A···S1^ix	3.02 (3)
N3···S1^i	3.1213 (17)	H4A···C2^i	3.04 (3)
N3···H3^vi	2.36 (3)	H4A···H2^i	2.47 (4)
C4···S1^viii	3.677 (2)	H4B···S1^viii	3.12 (3)
C2···H4A^i	3.04 (3)	H5B···S1^x	2.91 (3)
C2—S1—C5	92.59 (11)	C2^i—C2—H2	107.5 (14)
C2—N3—C4	110.20 (17)	N3—C4—H4A	106.5 (17)
C4—N3—H3	108.2 (18)	N3—C4—H4B	109.6 (19)
C2—N3—H3	108.1 (18)	C5—C4—H4A	110.1 (18)
S1—C2—C2^i	108.27 (14)	C5—C4—H4B	112.3 (17)
S1—C2—N3	107.22 (13)	H4A—C4—H4B	110 (2)
N3—C2—C2^i	111.96 (17)	S1—C5—H5A	108.3 (19)
N3—C4—C5	108.04 (19)	S1—C5—H5B	109.9 (16)
S1—C5—C4	103.97 (14)	C4—C5—H5A	111 (2)
S1—C2—H2	110.8 (15)	C4—C5—H5B	112.9 (19)
N3—C2—H2	111.1 (15)	H5A—C5—H5B	110 (3)
C5—S1—C2—N3	0.29 (16)	S1—C2—C2^i—S1^i	−180.00 (9)
C5—S1—C2—C2^i	121.26 (14)	S1—C2—C2^i—N3^i	62.02 (18)
C2—S1—C5—C4	−23.39 (18)	N3—C2—C2^i—S1^i	−62.02 (18)
C4—N3—C2—S1	24.8 (2)	N3—C2—C2^i—N3^i	180.00 (16)
C4—N3—C2—C2^i	−93.8 (2)	N3—C4—C5—S1	41.9 (2)
C2—N3—C4—C5	−44.4 (2)

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···N3^vii	0.89 (3)	2.36 (3)	3.183 (3)	153 (2)
C5—H5B···S^v	0.95 (3)	2.91 (3)	3.842 (3)	160.8 (6)

Symmetry codes: (v) −x−1/2, y+1/2, −z+1/2; (vii) −x+1/2, y+1/2, −z+1/2.