(4-Chloro­methyl-4-hydroxy-3-phenyl­thia­zolidin-2-yl­idene)­ammonium chloride acetone solvate

At 150 K, the title compound, C₁₀H₁₂ClN₂OS⁺·Cl^-·C₃H₆O, exists as discrete hydrogen-bonded [2 + 2]-dimers of cations and chloride anions. Of the two possible thia­zolidin-2-yl­idene­ammonium cations that may be formed by the reaction of 1,3-di­chloro­acetone with N-phenyl­thio­urea, the reported isomer is unable to eliminate water to form the corresponding thia­zole.

Key indicators

• Single-crystal X-ray study
• T = 150 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.043
• wR factor = 0.108
• Data-to-parameter ratio = 23.8

checkCIF/PLATON results

No syntax errors found



Alert level B
   Minimum crystal size given =   0.100
   Mid crystal size given     =   0.150
   Maximum crystal size given =   0.400
PLAT029_ALERT_3_B _diffrn_measured_fraction_theta_full Low .......       0.98

Alert level C
            colourless
            Hydrogen treatment given as mixed
            Wavelength given =    0.71073
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT431_ALERT_2_C Short Inter HL..A Contact  Cl2    ..  S1       =       3.44 Ang.
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          3
              Cl

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

   1 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
   1 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: X-AREA (Stoe & Cie, 2001); cell refinement: X-AREA; data reduction: X-RED (Stoe & Cie, 2001); program(s) used to solve structure: X-STEP32 (Stoe & Cie, 2001) and SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: WinGX (Farrugia, 1999) and SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX.

(4-Chloromethyl-4-hydroxymethyl-3-phenylthiazolidin-2-ylidene)ammonium chloride acetone solvate

Crystal data

C10H12ClN2OS^+·Cl^−·C3H6O	Z = 2
Mr = 337.25	F(000) = 352
Triclinic, P1	Dx = 1.354 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.5384 (19) Å	Cell parameters from 7613 reflections
b = 9.477 (2) Å	θ = 2.0–29.8°
c = 10.420 (2) Å	µ = 0.52 mm^−1
α = 97.115 (17)°	T = 150 K
β = 96.380 (17)°	Needle, colourless
γ = 95.024 (17)°	0.40 × 0.15 × 0.10 mm
V = 827.1 (3) Å^3

Data collection

Stoe IPDS-II diffractometer	2591 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.072
Graphite monochromator	θmax = 29.8°, θmin = 2.0°
Area detector scans	h = −11→9
12767 measured reflections	k = −13→13
4668 independent reflections	l = −14→14

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.043	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.109	w = 1/[σ^2(Fo^2) + (0.0525P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.83	(Δ/σ)max < 0.001
4668 reflections	Δρmax = 0.34 e Å^−3
196 parameters	Δρmin = −0.54 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.018 (3)

Special details

Experimental. The crystal was mounted under the perfluoro-polyether PFO-XR75 (Lancaster Synthesis). A total of 145 frames (5 minute exposure) were collected (phi/omega: 20/25–155, 120/20–180, delta-omega = 2 °.)

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 (Ų)

	x	y	z	Uiso*/Ueq
Cl1	0.89827 (9)	1.14840 (7)	0.41002 (6)	0.04244 (19)
Cl2	0.74652 (8)	0.76660 (6)	−0.15789 (6)	0.03427 (16)
S1	0.63212 (8)	1.15035 (6)	0.12290 (6)	0.03073 (16)
O1	0.9204 (2)	0.85673 (19)	0.11334 (19)	0.0337 (4)
H1	0.868 (5)	0.833 (4)	0.040 (4)	0.064 (11)*
O2	0.2658 (2)	0.7459 (2)	0.32112 (19)	0.0452 (5)
N1	0.6935 (2)	0.9160 (2)	0.21243 (19)	0.0264 (4)
N2	0.4372 (3)	0.9778 (2)	0.2295 (2)	0.0313 (5)
H2	0.404 (3)	0.902 (3)	0.269 (2)	0.029 (7)*
H3	0.358 (5)	1.045 (4)	0.216 (3)	0.067 (11)*
C1	0.5794 (3)	1.0005 (2)	0.1960 (2)	0.0261 (5)
C2	0.8529 (3)	0.9675 (2)	0.1803 (2)	0.0286 (5)
C3	0.8256 (3)	1.0919 (3)	0.1005 (2)	0.0321 (5)
H3A	0.8304	1.0599	0.0071	0.039*
H3B	0.9091	1.1722	0.1303	0.039*
C4	0.9676 (3)	1.0112 (3)	0.3029 (2)	0.0337 (6)
H4A	1.0718	1.0463	0.2793	0.040*
H4B	0.9820	0.9269	0.3486	0.040*
C5	0.6697 (3)	0.7852 (2)	0.2689 (2)	0.0288 (5)
C6	0.6894 (3)	0.7868 (3)	0.4021 (3)	0.0376 (6)
H6	0.7179	0.8743	0.4583	0.045*
C7	0.6671 (4)	0.6586 (3)	0.4536 (3)	0.0461 (7)
H7	0.6826	0.6580	0.5453	0.055*
C8	0.6222 (4)	0.5321 (3)	0.3710 (4)	0.0516 (8)
H8	0.6063	0.4449	0.4061	0.062*
C9	0.6003 (4)	0.5324 (3)	0.2374 (3)	0.0484 (8)
H9	0.5682	0.4454	0.1813	0.058*
C10	0.6247 (3)	0.6585 (3)	0.1850 (3)	0.0366 (6)
H10	0.6111	0.6587	0.0933	0.044*
C11	0.1822 (3)	0.6487 (3)	0.2529 (3)	0.0375 (6)
C12	0.0629 (4)	0.5561 (3)	0.3090 (3)	0.0532 (8)
H12A	−0.0439	0.5682	0.2697	0.064*
H12B	0.0720	0.5839	0.4035	0.064*
H12C	0.0829	0.4558	0.2904	0.064*
C13	0.1916 (4)	0.6152 (3)	0.1106 (3)	0.0440 (7)
H13A	0.2718	0.6829	0.0848	0.053*
H13B	0.0884	0.6229	0.0619	0.053*
H13C	0.2207	0.5177	0.0916	0.053*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0476 (4)	0.0404 (4)	0.0349 (3)	0.0012 (3)	−0.0030 (3)	−0.0023 (3)
Cl2	0.0315 (4)	0.0298 (3)	0.0415 (3)	0.0047 (3)	0.0044 (3)	0.0043 (2)
S1	0.0312 (4)	0.0264 (3)	0.0367 (3)	0.0047 (3)	0.0074 (3)	0.0083 (2)
O1	0.0311 (10)	0.0365 (10)	0.0358 (10)	0.0113 (8)	0.0081 (8)	0.0045 (8)
O2	0.0421 (12)	0.0419 (11)	0.0511 (12)	−0.0045 (9)	0.0150 (10)	0.0019 (9)
N1	0.0239 (11)	0.0247 (9)	0.0313 (10)	0.0023 (8)	0.0054 (8)	0.0048 (8)
N2	0.0251 (12)	0.0303 (11)	0.0401 (12)	0.0035 (9)	0.0074 (9)	0.0077 (9)
C1	0.0264 (13)	0.0252 (11)	0.0261 (11)	0.0024 (9)	0.0042 (10)	0.0002 (9)
C2	0.0250 (13)	0.0282 (12)	0.0339 (12)	0.0024 (10)	0.0080 (10)	0.0058 (9)
C3	0.0288 (14)	0.0344 (13)	0.0350 (13)	0.0031 (11)	0.0079 (11)	0.0089 (10)
C4	0.0290 (14)	0.0373 (13)	0.0359 (13)	0.0028 (11)	0.0042 (11)	0.0087 (11)
C5	0.0248 (13)	0.0275 (11)	0.0354 (12)	0.0040 (10)	0.0055 (10)	0.0070 (9)
C6	0.0346 (15)	0.0396 (14)	0.0402 (14)	0.0005 (12)	0.0075 (12)	0.0113 (11)
C7	0.0362 (17)	0.0567 (18)	0.0509 (17)	0.0026 (14)	0.0092 (14)	0.0275 (15)
C8	0.0394 (17)	0.0398 (16)	0.084 (2)	0.0052 (13)	0.0174 (17)	0.0306 (16)
C9	0.0448 (18)	0.0271 (13)	0.076 (2)	0.0036 (12)	0.0170 (16)	0.0080 (13)
C10	0.0333 (15)	0.0292 (12)	0.0479 (15)	0.0037 (11)	0.0088 (12)	0.0035 (11)
C11	0.0306 (15)	0.0278 (13)	0.0568 (16)	0.0070 (11)	0.0114 (13)	0.0083 (12)
C12	0.051 (2)	0.0377 (15)	0.073 (2)	−0.0041 (14)	0.0263 (17)	0.0050 (14)
C13	0.0466 (18)	0.0376 (14)	0.0491 (16)	0.0071 (13)	0.0038 (14)	0.0102 (12)

Geometric parameters (Å, º)

Cl1—C4	1.791 (3)	C5—C10	1.392 (3)
S1—C1	1.741 (2)	C6—C7	1.395 (4)
S1—C3	1.817 (3)	C6—H6	0.9500
O1—C2	1.391 (3)	C7—C8	1.383 (5)
O1—H1	0.84 (4)	C7—H7	0.9500
O2—C11	1.214 (3)	C8—C9	1.385 (5)
N1—C1	1.324 (3)	C8—H8	0.9500
N1—C5	1.445 (3)	C9—C10	1.383 (4)
N1—C2	1.493 (3)	C9—H9	0.9500
N2—C1	1.308 (3)	C10—H10	0.9500
N2—H2	0.91 (3)	C11—C13	1.489 (4)
N2—H3	0.98 (4)	C11—C12	1.500 (4)
C2—C4	1.511 (4)	C12—H12A	0.9800
C2—C3	1.544 (3)	C12—H12B	0.9800
C3—H3A	0.9900	C12—H12C	0.9800
C3—H3B	0.9900	C13—H13A	0.9800
C4—H4A	0.9900	C13—H13B	0.9800
C4—H4B	0.9900	C13—H13C	0.9800
C5—C6	1.377 (4)
C1—S1—C3	91.66 (11)	C10—C5—N1	118.1 (2)
C2—O1—H1	109 (3)	C5—C6—C7	119.3 (3)
C1—N1—C5	121.9 (2)	C5—C6—H6	120.4
C1—N1—C2	117.01 (19)	C7—C6—H6	120.4
C5—N1—C2	120.9 (2)	C8—C7—C6	119.9 (3)
C1—N2—H2	124.2 (17)	C8—C7—H7	120.1
C1—N2—H3	121 (2)	C6—C7—H7	120.1
H2—N2—H3	115 (3)	C7—C8—C9	120.2 (3)
N2—C1—N1	125.0 (2)	C7—C8—H8	119.9
N2—C1—S1	120.65 (19)	C9—C8—H8	119.9
N1—C1—S1	114.36 (18)	C10—C9—C8	120.4 (3)
O1—C2—N1	110.61 (19)	C10—C9—H9	119.8
O1—C2—C4	103.7 (2)	C8—C9—H9	119.8
N1—C2—C4	110.77 (19)	C9—C10—C5	118.9 (3)
O1—C2—C3	113.15 (19)	C9—C10—H10	120.5
N1—C2—C3	105.67 (19)	C5—C10—H10	120.5
C4—C2—C3	113.1 (2)	O2—C11—C13	122.4 (3)
C2—C3—S1	108.77 (16)	O2—C11—C12	121.0 (3)
C2—C3—H3A	109.9	C13—C11—C12	116.7 (3)
S1—C3—H3A	109.9	C11—C12—H12A	109.5
C2—C3—H3B	109.9	C11—C12—H12B	109.5
S1—C3—H3B	109.9	H12A—C12—H12B	109.5
H3A—C3—H3B	108.3	C11—C12—H12C	109.5
C2—C4—Cl1	111.56 (18)	H12A—C12—H12C	109.5
C2—C4—H4A	109.3	H12B—C12—H12C	109.5
Cl1—C4—H4A	109.3	C11—C13—H13A	109.5
C2—C4—H4B	109.3	C11—C13—H13B	109.5
Cl1—C4—H4B	109.3	H13A—C13—H13B	109.5
H4A—C4—H4B	108.0	C11—C13—H13C	109.5
C6—C5—C10	121.2 (2)	H13A—C13—H13C	109.5
C6—C5—N1	120.7 (2)	H13B—C13—H13C	109.5
C5—N1—C1—N2	1.1 (4)	O1—C2—C4—Cl1	−176.82 (15)
C2—N1—C1—N2	−173.9 (2)	N1—C2—C4—Cl1	−58.2 (2)
C5—N1—C1—S1	−178.63 (17)	C3—C2—C4—Cl1	60.2 (2)
C2—N1—C1—S1	6.3 (3)	C1—N1—C5—C6	−85.4 (3)
C3—S1—C1—N2	−176.0 (2)	C2—N1—C5—C6	89.5 (3)
C3—S1—C1—N1	3.76 (19)	C1—N1—C5—C10	93.9 (3)
C1—N1—C2—O1	−137.7 (2)	C2—N1—C5—C10	−91.2 (3)
C5—N1—C2—O1	47.2 (3)	C10—C5—C6—C7	1.3 (4)
C1—N1—C2—C4	108.0 (2)	N1—C5—C6—C7	−179.4 (2)
C5—N1—C2—C4	−67.1 (3)	C5—C6—C7—C8	−1.4 (4)
C1—N1—C2—C3	−14.9 (3)	C6—C7—C8—C9	0.4 (5)
C5—N1—C2—C3	170.0 (2)	C7—C8—C9—C10	0.7 (5)
O1—C2—C3—S1	137.40 (19)	C8—C9—C10—C5	−0.8 (4)
N1—C2—C3—S1	16.2 (2)	C6—C5—C10—C9	−0.2 (4)
C4—C2—C3—S1	−105.1 (2)	N1—C5—C10—C9	−179.5 (2)
C1—S1—C3—C2	−11.91 (19)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···Cl2	0.84 (4)	2.19 (4)	3.028 (2)	176 (4)
N2—H2···O2	0.91 (3)	1.98 (3)	2.854 (3)	161 (2)
N2—H3···Cl2^i	0.98 (4)	2.19 (4)	3.121 (2)	159 (3)

Symmetry code: (i) −x+1, −y+2, −z.