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In the title compound, C
3H
6N
2O
2S, the five-membered ring has an envelope conformation and the two hydroxyl groups lie on opposite sides of the ring. The crystal structure is stablized by intermolecular O—H
S and N—-H
O hydrogen bonds, and also a close O
O intermolecular approach, to form a two-dimensional network parallel to
bc.
Supporting information
CCDC reference: 651390
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.003 Å
- R factor = 0.028
- wR factor = 0.074
- Data-to-parameter ratio = 12.8
checkCIF/PLATON results
No syntax errors found
Alert level C
ABSTM02_ALERT_3_C The ratio of expected to reported Tmax/Tmin(RR') is < 0.90
Tmin and Tmax reported: 0.644 0.929
Tmin(prime) and Tmax expected: 0.777 0.929
RR(prime) = 0.829
Please check that your absorption correction is appropriate.
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.97
PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large ............. 0.82
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ?
PLAT154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000) 300 Deg.
Alert level G
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
5 ALERT level C = Check and explain
2 ALERT level G = General alerts; check
3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
0 ALERT type 2 Indicator that the structure model may be wrong or deficient
3 ALERT type 3 Indicator that the structure quality may be low
1 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXL97; software used to prepare material for publication: SHELXL97.
trans-4,5-Dihydroxyimidazolidine-2-thione
top
Crystal data top
C3H6N2O2S | Z = 2 |
Mr = 134.16 | F(000) = 140 |
Triclinic, P1 | Dx = 1.632 Mg m−3 |
a = 5.8092 (13) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 6.5152 (13) Å | Cell parameters from 1216 reflections |
c = 7.9189 (17) Å | θ = 2.7–27.3° |
α = 98.595 (3)° | µ = 0.49 mm−1 |
β = 106.740 (3)° | T = 293 K |
γ = 102.494 (3)° | Block, colourless |
V = 272.93 (10) Å3 | 0.50 × 0.40 × 0.15 mm |
Data collection top
Bruker SMART CCD area-detector diffractometer | 938 independent reflections |
Radiation source: fine-focus sealed tube | 913 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.014 |
ω scans | θmax = 25.0°, θmin = 2.7° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −5→6 |
Tmin = 0.644, Tmax = 0.929 | k = −7→7 |
1137 measured reflections | l = −9→9 |
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)] = 0.028 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.074 | H-atom parameters constrained |
S = 1.10 | w = 1/[σ2(Fo2) + (0.0266P)2 + 0.1391P] where P = (Fo2 + 2Fc2)/3 |
938 reflections | (Δ/σ)max < 0.001 |
73 parameters | Δρmax = 0.21 e Å−3 |
0 restraints | Δρmin = −0.23 e Å−3 |
Special details top
Experimental. 1H NMR (DMSO, 400 MHz, δ, p.p.m.): 8.863 (s, 2H, 2NH), 6.272–6.254 (d, J =
7.2 Hz, 2H, 2CH), 4.740–4.723 (d, J = 6.8 Hz, 2H, 2OH). |
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 | Uiso*/Ueq | |
S1 | 0.17083 (9) | 0.20558 (7) | 0.72371 (6) | 0.04000 (19) | |
O1 | 0.9700 (2) | 0.7190 (2) | 0.90814 (17) | 0.0393 (3) | |
H1 | 0.9312 | 0.7162 | 0.9996 | 0.059* | |
O2 | 0.4707 (3) | 0.8652 (2) | 0.62620 (19) | 0.0480 (4) | |
H2 | 0.3942 | 0.9534 | 0.6447 | 0.072* | |
N1 | 0.6030 (3) | 0.4520 (2) | 0.7146 (2) | 0.0347 (4) | |
H3 | 0.6452 | 0.3432 | 0.6696 | 0.042* | |
N2 | 0.3806 (3) | 0.6342 (2) | 0.8159 (2) | 0.0335 (3) | |
H4 | 0.2756 | 0.6610 | 0.8677 | 0.040* | |
C1 | 0.3912 (3) | 0.4357 (3) | 0.7531 (2) | 0.0295 (4) | |
C2 | 0.7535 (3) | 0.6738 (3) | 0.7572 (2) | 0.0327 (4) | |
H5 | 0.7998 | 0.7047 | 0.6521 | 0.039* | |
C3 | 0.5665 (3) | 0.7984 (3) | 0.7863 (2) | 0.0323 (4) | |
H6 | 0.6443 | 0.9208 | 0.8912 | 0.039* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
S1 | 0.0405 (3) | 0.0344 (3) | 0.0428 (3) | 0.0047 (2) | 0.0178 (2) | 0.0021 (2) |
O1 | 0.0280 (6) | 0.0548 (8) | 0.0384 (7) | 0.0135 (6) | 0.0153 (5) | 0.0084 (6) |
O2 | 0.0641 (9) | 0.0502 (8) | 0.0483 (8) | 0.0352 (7) | 0.0259 (7) | 0.0231 (7) |
N1 | 0.0347 (8) | 0.0339 (8) | 0.0411 (9) | 0.0153 (6) | 0.0188 (7) | 0.0043 (6) |
N2 | 0.0304 (8) | 0.0337 (8) | 0.0434 (9) | 0.0133 (6) | 0.0202 (7) | 0.0068 (6) |
C1 | 0.0305 (9) | 0.0354 (9) | 0.0235 (8) | 0.0124 (7) | 0.0082 (7) | 0.0062 (7) |
C2 | 0.0313 (9) | 0.0374 (9) | 0.0344 (9) | 0.0119 (7) | 0.0157 (7) | 0.0093 (7) |
C3 | 0.0326 (9) | 0.0328 (9) | 0.0354 (9) | 0.0121 (7) | 0.0148 (7) | 0.0079 (7) |
Geometric parameters (Å, º) top
S1—C1 | 1.684 (2) | N1—H3 | 0.8600 |
O1—C2 | 1.402 (2) | N2—C1 | 1.335 (2) |
O1—H1 | 0.8200 | N2—C3 | 1.445 (2) |
O2—C3 | 1.403 (2) | N2—H4 | 0.8600 |
O2—H2 | 0.8200 | C2—C3 | 1.537 (2) |
N1—C1 | 1.336 (2) | C2—H5 | 0.9800 |
N1—C2 | 1.451 (2) | C3—H6 | 0.9800 |
| | | |
C2—O1—H1 | 109.5 | O1—C2—C3 | 113.75 (14) |
C3—O2—H2 | 109.5 | N1—C2—C3 | 101.45 (13) |
C1—N1—C2 | 112.43 (14) | O1—C2—H5 | 109.6 |
C1—N1—H3 | 123.8 | N1—C2—H5 | 109.6 |
C2—N1—H3 | 123.8 | C3—C2—H5 | 109.6 |
C1—N2—C3 | 111.88 (14) | O2—C3—N2 | 112.14 (15) |
C1—N2—H4 | 124.1 | O2—C3—C2 | 107.41 (14) |
C3—N2—H4 | 124.1 | N2—C3—C2 | 101.72 (13) |
N2—C1—N1 | 108.41 (15) | O2—C3—H6 | 111.7 |
N2—C1—S1 | 125.37 (13) | N2—C3—H6 | 111.7 |
N1—C1—S1 | 126.21 (13) | C2—C3—H6 | 111.7 |
O1—C2—N1 | 112.67 (14) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···S1i | 0.82 | 2.44 | 3.245 (3) | 167 |
O2—H2···S1ii | 0.82 | 2.42 | 3.238 (3) | 175 |
N1—H3···O2iii | 0.86 | 2.35 | 3.004 (2) | 133 |
N2—H4···O1iv | 0.86 | 2.00 | 2.826 (2) | 162 |
Symmetry codes: (i) −x+1, −y+1, −z+2; (ii) x, y+1, z; (iii) −x+1, −y+1, −z+1; (iv) x−1, y, z. |
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