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All the five-membered rings of the title mol­ecule, C14H18N2O2S2, adopt envelope conformations. Inter­molecular C—H...O hydrogen bonds link the mol­ecules into a two-dimensional network parallel to the ab plane.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806032259/om2051sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806032259/om2051Isup2.hkl
Contains datablock I

CCDC reference: 621461

Key indicators

  • Single-crystal X-ray study
  • T = 100 K
  • Mean [sigma](C-C) = 0.001 Å
  • R factor = 0.036
  • wR factor = 0.106
  • Data-to-parameter ratio = 48.8

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT432_ALERT_2_C Short Inter X...Y Contact O1 .. C1 .. 2.94 Ang.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 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 1 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: APEX2 (Bruker, 2005); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 1998); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003).

5-(Phenylsulfonyl)perhydrothiazolo[3,4-a]pyrrolo[4,5-c]pyrrole top
Crystal data top
C14H18N2O2S2F(000) = 656
Mr = 310.42Dx = 1.396 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 7465 reflections
a = 6.5439 (1) Åθ = 2.3–36.7°
b = 9.8794 (1) ŵ = 0.36 mm1
c = 23.0360 (3) ÅT = 100 K
β = 97.451 (1)°Block, colourless
V = 1476.70 (3) Å30.39 × 0.33 × 0.26 mm
Z = 4
Data collection top
Bruker SMART APEX2 CCD area-detector
diffractometer
8831 independent reflections
Radiation source: fine-focus sealed tube6960 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.036
Detector resolution: 8.33 pixels mm-1θmax = 39.5°, θmin = 1.8°
ω scansh = 1110
Absorption correction: multi-scan
(SADABS; Bruker, 2005)
k = 1617
Tmin = 0.845, Tmax = 0.912l = 3940
71353 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.036Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.106H-atom parameters constrained
S = 1.07 w = 1/[σ2(Fo2) + (0.056P)2 + 0.1806P]
where P = (Fo2 + 2Fc2)/3
8831 reflections(Δ/σ)max = 0.002
181 parametersΔρmax = 0.54 e Å3
0 restraintsΔρmin = 0.40 e Å3
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
xyzUiso*/Ueq
S10.43595 (3)0.66899 (2)0.452502 (9)0.02131 (5)
S20.63005 (3)0.397830 (18)0.181145 (8)0.01417 (4)
O10.84809 (9)0.40497 (7)0.19902 (3)0.02134 (12)
O20.53783 (10)0.27040 (6)0.16247 (3)0.01899 (11)
N10.51846 (9)0.44792 (6)0.23644 (3)0.01409 (10)
N20.52613 (10)0.50158 (6)0.36838 (3)0.01465 (10)
C10.29114 (11)0.45604 (8)0.22895 (3)0.01707 (13)
H1A0.22790.36620.22000.020*
H1B0.23950.52040.19750.020*
C20.24786 (11)0.50719 (8)0.28897 (3)0.01598 (12)
H20.12860.57130.28480.019*
C30.44914 (11)0.58020 (7)0.31540 (3)0.01435 (11)
H30.42200.67660.32530.017*
C40.59510 (12)0.57053 (8)0.26885 (3)0.01587 (12)
H4A0.58410.65130.24320.019*
H4B0.74000.55950.28680.019*
C50.21661 (14)0.39393 (9)0.33296 (4)0.02208 (15)
H5A0.06950.38540.33830.027*
H5B0.26590.30590.31970.027*
C60.34566 (12)0.43974 (8)0.38945 (4)0.01794 (13)
H60.38760.36030.41520.022*
C70.23788 (13)0.54860 (9)0.42352 (4)0.02112 (15)
H7A0.17470.50620.45580.025*
H7B0.12850.59490.39710.025*
C80.63398 (12)0.58094 (8)0.41476 (3)0.01746 (13)
H8A0.72420.64790.39870.021*
H8B0.72060.52190.44260.021*
C90.56634 (12)0.51455 (8)0.12363 (3)0.01612 (12)
C100.38319 (14)0.49787 (9)0.08606 (4)0.02042 (14)
H100.29440.42380.09090.025*
C110.33233 (17)0.59170 (10)0.04130 (4)0.02673 (18)
H110.20770.58210.01550.032*
C120.46417 (17)0.69929 (10)0.03451 (4)0.02879 (19)
H120.43000.76230.00360.035*
C130.64488 (17)0.71541 (10)0.07241 (5)0.02948 (19)
H130.73320.78980.06760.035*
C140.69757 (14)0.62325 (9)0.11750 (4)0.02310 (16)
H140.82110.63420.14370.028*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.02642 (10)0.02007 (9)0.01753 (9)0.00358 (7)0.00325 (7)0.00138 (6)
S20.01155 (7)0.01335 (8)0.01756 (8)0.00108 (5)0.00170 (5)0.00131 (5)
O10.0106 (2)0.0266 (3)0.0266 (3)0.00259 (19)0.0016 (2)0.0012 (2)
O20.0222 (3)0.0122 (2)0.0225 (3)0.00001 (19)0.0026 (2)0.00270 (19)
N10.0106 (2)0.0151 (2)0.0164 (3)0.00087 (18)0.00097 (18)0.00277 (19)
N20.0150 (2)0.0143 (2)0.0143 (3)0.00027 (19)0.00037 (19)0.00163 (19)
C10.0107 (3)0.0227 (3)0.0174 (3)0.0004 (2)0.0005 (2)0.0032 (2)
C20.0131 (3)0.0189 (3)0.0159 (3)0.0003 (2)0.0018 (2)0.0004 (2)
C30.0156 (3)0.0130 (3)0.0142 (3)0.0005 (2)0.0008 (2)0.0007 (2)
C40.0164 (3)0.0154 (3)0.0158 (3)0.0044 (2)0.0019 (2)0.0017 (2)
C50.0224 (4)0.0223 (4)0.0213 (4)0.0082 (3)0.0015 (3)0.0014 (3)
C60.0185 (3)0.0176 (3)0.0177 (3)0.0024 (2)0.0021 (2)0.0036 (2)
C70.0188 (3)0.0274 (4)0.0176 (3)0.0018 (3)0.0037 (3)0.0035 (3)
C80.0168 (3)0.0190 (3)0.0159 (3)0.0003 (2)0.0005 (2)0.0000 (2)
C90.0163 (3)0.0152 (3)0.0173 (3)0.0004 (2)0.0038 (2)0.0008 (2)
C100.0217 (3)0.0193 (3)0.0195 (3)0.0004 (3)0.0004 (3)0.0003 (3)
C110.0321 (5)0.0255 (4)0.0213 (4)0.0047 (3)0.0014 (3)0.0020 (3)
C120.0405 (5)0.0222 (4)0.0249 (4)0.0065 (4)0.0088 (4)0.0064 (3)
C130.0345 (5)0.0208 (4)0.0349 (5)0.0027 (3)0.0113 (4)0.0069 (3)
C140.0214 (4)0.0202 (3)0.0284 (4)0.0047 (3)0.0056 (3)0.0017 (3)
Geometric parameters (Å, º) top
S1—C71.8210 (10)C5—C61.5254 (12)
S1—C81.8665 (8)C5—H5A0.99
S2—O11.4346 (6)C5—H5B0.99
S2—O21.4376 (6)C6—C71.5536 (12)
S2—N11.6253 (7)C6—H61.00
S2—C91.7651 (8)C7—H7A0.99
N1—C41.4762 (10)C7—H7B0.99
N1—C11.4773 (9)C8—H8A0.99
N2—C81.4348 (10)C8—H8B0.99
N2—C61.4670 (10)C9—C141.3936 (11)
N2—C31.4789 (10)C9—C101.3941 (12)
C1—C21.5325 (11)C10—C111.3944 (12)
C1—H1A0.99C10—H100.95
C1—H1B0.99C11—C121.3906 (15)
C2—C51.5408 (12)C11—H110.95
C2—C31.5549 (11)C12—C131.3851 (16)
C2—H21.00C12—H120.95
C3—C41.5288 (10)C13—C141.3906 (13)
C3—H31.00C13—H130.95
C4—H4A0.99C14—H140.95
C4—H4B0.99
C7—S1—C891.66 (4)C6—C5—H5B111.0
O1—S2—O2119.49 (4)C2—C5—H5B111.0
O1—S2—N1106.94 (4)H5A—C5—H5B109.0
O2—S2—N1106.70 (4)N2—C6—C5102.81 (6)
O1—S2—C9108.21 (4)N2—C6—C7108.45 (6)
O2—S2—C9107.36 (4)C5—C6—C7113.52 (7)
N1—S2—C9107.63 (3)N2—C6—H6110.6
C4—N1—C1106.58 (6)C5—C6—H6110.6
C4—N1—S2119.24 (5)C7—C6—H6110.6
C1—N1—S2118.23 (5)C6—C7—S1106.81 (5)
C8—N2—C6108.69 (6)C6—C7—H7A110.4
C8—N2—C3114.18 (6)S1—C7—H7A110.4
C6—N2—C3106.80 (6)C6—C7—H7B110.4
N1—C1—C2102.34 (6)S1—C7—H7B110.4
N1—C1—H1A111.3H7A—C7—H7B108.6
C2—C1—H1A111.3N2—C8—S1107.30 (5)
N1—C1—H1B111.3N2—C8—H8A110.3
C2—C1—H1B111.3S1—C8—H8A110.3
H1A—C1—H1B109.2N2—C8—H8B110.3
C1—C2—C5114.18 (7)S1—C8—H8B110.3
C1—C2—C3105.06 (6)H8A—C8—H8B108.5
C5—C2—C3104.91 (6)C14—C9—C10121.31 (8)
C1—C2—H2110.8C14—C9—S2119.39 (7)
C5—C2—H2110.8C10—C9—S2119.28 (6)
C3—C2—H2110.8C9—C10—C11118.95 (8)
N2—C3—C4111.66 (6)C9—C10—H10120.5
N2—C3—C2105.07 (6)C11—C10—H10120.5
C4—C3—C2105.72 (6)C12—C11—C10119.95 (9)
N2—C3—H3111.4C12—C11—H11120.0
C4—C3—H3111.4C10—C11—H11120.0
C2—C3—H3111.4C13—C12—C11120.56 (9)
N1—C4—C3101.76 (6)C13—C12—H12119.7
N1—C4—H4A111.4C11—C12—H12119.7
C3—C4—H4A111.4C12—C13—C14120.28 (9)
N1—C4—H4B111.4C12—C13—H13119.9
C3—C4—H4B111.4C14—C13—H13119.9
H4A—C4—H4B109.3C13—C14—C9118.94 (9)
C6—C5—C2103.86 (6)C13—C14—H14120.5
C6—C5—H5A111.0C9—C14—H14120.5
C2—C5—H5A111.0
O1—S2—N1—C445.23 (7)C3—N2—C6—C541.05 (8)
O2—S2—N1—C4174.17 (6)C8—N2—C6—C744.20 (8)
C9—S2—N1—C470.85 (6)C3—N2—C6—C779.43 (7)
O1—S2—N1—C1177.43 (6)C2—C5—C6—N237.18 (8)
O2—S2—N1—C153.62 (7)C2—C5—C6—C779.75 (8)
C9—S2—N1—C161.35 (6)N2—C6—C7—S127.22 (8)
C4—N1—C1—C241.85 (8)C5—C6—C7—S1140.80 (6)
S2—N1—C1—C2179.44 (5)C8—S1—C7—C64.14 (6)
N1—C1—C2—C590.89 (8)C6—N2—C8—S140.02 (7)
N1—C1—C2—C323.50 (7)C3—N2—C8—S179.09 (7)
C8—N2—C3—C497.70 (7)C7—S1—C8—N220.05 (6)
C6—N2—C3—C4142.13 (6)O1—S2—C9—C1422.38 (8)
C8—N2—C3—C2148.16 (6)O2—S2—C9—C14152.60 (7)
C6—N2—C3—C227.99 (7)N1—S2—C9—C1492.87 (7)
C1—C2—C3—N2116.82 (6)O1—S2—C9—C10159.11 (7)
C5—C2—C3—N23.88 (8)O2—S2—C9—C1028.89 (8)
C1—C2—C3—C41.40 (8)N1—S2—C9—C1085.65 (7)
C5—C2—C3—C4122.11 (7)C14—C9—C10—C110.51 (13)
C1—N1—C4—C342.57 (7)S2—C9—C10—C11178.99 (7)
S2—N1—C4—C3179.65 (5)C9—C10—C11—C120.38 (14)
N2—C3—C4—N188.00 (7)C10—C11—C12—C130.93 (15)
C2—C3—C4—N125.74 (7)C11—C12—C13—C140.58 (16)
C1—C2—C5—C6134.68 (7)C12—C13—C14—C90.31 (15)
C3—C2—C5—C620.20 (8)C10—C9—C14—C130.86 (13)
C8—N2—C6—C5164.68 (6)S2—C9—C14—C13179.34 (7)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C1—H1A···O1i0.992.502.9355 (9)106
C7—H7B···O2ii0.992.383.3247 (11)158
C8—H8A···O2iii0.992.543.5031 (10)165
Symmetry codes: (i) x1, y, z; (ii) x+1/2, y+1/2, z+1/2; (iii) x+3/2, y+1/2, z+1/2.
 

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