C—H...O contacts in the crystal structure of 1,3-di­thiane 1,1,3,3-tetra­oxide

In the title compound, the mol­ecules stack parallel with the a axis with multiple H...O contacts involving the axial H and O atoms. Many more H...O contacts between the stacks exist, which mostly involve the equatorial hydrogen and oxygen atoms. The highly polarized hydrogen atoms of the –SO₂—CH₂—SO₂– moiety make no exceptionally short H...O contacts but clearly play a leading role in the formation of the stacks.

Key indicators

• Single-crystal X-ray study
• T = 120 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.027
• wR factor = 0.055
• Data-to-parameter ratio = 12.3

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax < 18) ........       6.21 Note
PLAT222_ALERT_3_C NonSolvent Resd 1  H   Uiso(max)/Uiso(min) Range       10.0 Ratio
PLAT245_ALERT_2_C U(iso) H6A       Smaller than U(eq) C6        by      0.013 Ang   2
PLAT340_ALERT_3_C Low Bond Precision on  C-C Bonds ...............     0.0055 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H2A      ..O3A      .       2.76 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H2A      ..O3E      .       2.91 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H4E      ..O3A      .       2.70 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H4E      ..O3E      .       2.63 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H5E      ..O1A      .       2.91 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H6A      ..O1E      .       2.65 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H6E      ..O1A      .       2.81 Ang.

Alert level G
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600          3 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          2 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
  11 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   2 ALERT level G = General information/check it is not something unexpected

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 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
   8 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: APEX3 (Bruker, 2015); cell refinement: SAINT (Bruker, 2015); data reduction: SAINT (Bruker, 2015); program(s) used to solve structure: olex2.solve (Dolomanov et al., 2009); program(s) used to refine structure: SHELXL2018/3 (Sheldrick, 2015); molecular graphics: CrystalMaker (Palmer, 2014); software used to prepare material for publication: publCIF (Westrip, 2010).

1,3-Dithiane 1,1,3,3-tetraoxide

Crystal data

C4H8O4S2	F(000) = 192
Mr = 184.22	Dx = 1.760 Mg m^−3
Monoclinic, Pn	Mo Kα radiation, λ = 0.71073 Å
a = 4.9472 (5) Å	Cell parameters from 5408 reflections
b = 9.9021 (10) Å	θ = 3.5–27.1°
c = 7.1002 (7) Å	µ = 0.72 mm^−1
β = 91.464 (3)°	T = 120 K
V = 347.71 (6) Å^3	Rod, colorless
Z = 2	0.54 × 0.11 × 0.05 mm

Data collection

Bruker PHOTON-II diffractometer	1513 independent reflections
Radiation source: fine-focus sealed tube	1473 reflections with I > 2σ(I)
Bruker TRIUMPH curved-graphite monochromator	Rint = 0.039
Detector resolution: 7.41 pixels mm^-1	θmax = 27.1°, θmin = 2.1°
combination of ω and φ–scans	h = −6→6
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	k = −12→12
Tmin = 0.579, Tmax = 0.746	l = −9→9
6109 measured reflections

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)] = 0.027	All H-atom parameters refined
wR(F^2) = 0.055	w = 1/[σ^2(Fo^2) + (0.0163P)^2 + 0.148P] where P = (Fo^2 + 2Fc^2)/3
S = 1.15	(Δ/σ)max < 0.001
1513 reflections	Δρmax = 0.28 e Å^−3
123 parameters	Δρmin = −0.40 e Å^−3
2 restraints	Absolute structure: Flack x determined using 682 quotients [(I^+)-(I^-)]/[(I^+)+(I^-)] (Parsons et al., 2013).
Primary atom site location: iterative	Absolute structure parameter: 0.07 (4)

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
S1	0.56801 (14)	0.16084 (8)	0.31351 (11)	0.01036 (19)
S3	0.54595 (15)	0.42138 (8)	0.52142 (12)	0.01083 (19)
O1a	0.8592 (5)	0.1643 (3)	0.3226 (4)	0.0167 (5)
O1e	0.4403 (5)	0.0944 (3)	0.1549 (4)	0.0173 (6)
O3a	0.8376 (5)	0.4249 (3)	0.5291 (4)	0.0162 (5)
O3e	0.4048 (5)	0.5484 (2)	0.5189 (4)	0.0170 (6)
C2	0.4419 (7)	0.3292 (4)	0.3144 (5)	0.0125 (7)
C4	0.4299 (7)	0.3185 (4)	0.7058 (5)	0.0155 (7)
C5	0.5438 (8)	0.1749 (4)	0.6975 (5)	0.0166 (8)
C6	0.4464 (8)	0.0935 (4)	0.5261 (5)	0.0155 (8)
H2a	0.244 (8)	0.323 (3)	0.309 (6)	0.006 (9)*
H2e	0.515 (8)	0.376 (4)	0.206 (6)	0.004 (9)*
H4a	0.231 (8)	0.326 (4)	0.697 (5)	0.007 (9)*
H4e	0.489 (7)	0.362 (4)	0.817 (6)	0.011 (10)*
H5a	0.724 (9)	0.179 (4)	0.706 (6)	0.011 (10)*
H5e	0.475 (9)	0.123 (5)	0.807 (7)	0.025 (12)*
H6a	0.255 (7)	0.094 (4)	0.513 (6)	0.002 (8)*
H6e	0.523 (8)	0.005 (4)	0.529 (6)	0.007 (8)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0083 (4)	0.0114 (4)	0.0114 (4)	0.0005 (4)	0.0006 (3)	−0.0008 (3)
S3	0.0098 (4)	0.0107 (4)	0.0120 (4)	−0.0004 (3)	−0.0004 (3)	−0.0015 (3)
O1a	0.0091 (12)	0.0200 (13)	0.0209 (14)	0.0015 (10)	0.0017 (10)	−0.0001 (11)
O1e	0.0161 (13)	0.0203 (13)	0.0153 (13)	−0.0022 (11)	−0.0004 (10)	−0.0076 (10)
O3a	0.0085 (12)	0.0191 (13)	0.0210 (13)	−0.0026 (10)	−0.0019 (10)	−0.0017 (11)
O3e	0.0167 (14)	0.0120 (13)	0.0224 (14)	0.0027 (10)	0.0024 (11)	−0.0019 (10)
C2	0.0120 (18)	0.0124 (17)	0.0130 (17)	−0.0006 (13)	−0.0015 (14)	0.0003 (13)
C4	0.0146 (18)	0.0211 (19)	0.0108 (16)	0.0000 (15)	0.0023 (14)	−0.0010 (14)
C5	0.0138 (19)	0.022 (2)	0.0136 (19)	0.0005 (15)	0.0007 (15)	0.0071 (14)
C6	0.0119 (16)	0.0177 (19)	0.0170 (18)	0.0002 (14)	−0.0002 (14)	0.0021 (14)

Geometric parameters (Å, º)

S1—O1e	1.437 (3)	C2—H2e	0.97 (4)
S1—O1a	1.441 (3)	C4—C5	1.531 (5)
S1—C6	1.769 (4)	C4—H4a	0.99 (4)
S1—C2	1.780 (4)	C4—H4e	0.94 (4)
S3—O3e	1.439 (3)	C5—C6	1.528 (5)
S3—O3a	1.443 (3)	C5—H5a	0.89 (4)
S3—C4	1.767 (4)	C5—H5e	1.00 (5)
S3—C2	1.795 (4)	C6—H6a	0.95 (4)
C2—H2a	0.98 (4)	C6—H6e	0.95 (4)
O1e—S1—O1a	117.72 (16)	C5—C4—S3	112.3 (3)
O1e—S1—C6	110.10 (17)	C5—C4—H4a	116 (2)
O1a—S1—C6	109.38 (17)	S3—C4—H4a	105 (2)
O1e—S1—C2	106.54 (16)	C5—C4—H4e	111 (2)
O1a—S1—C2	109.14 (16)	S3—C4—H4e	105 (3)
C6—S1—C2	102.89 (17)	H4a—C4—H4e	108 (3)
O3e—S3—O3a	117.64 (15)	C6—C5—C4	114.3 (3)
O3e—S3—C4	110.27 (17)	C6—C5—H5a	112 (3)
O3a—S3—C4	109.24 (17)	C4—C5—H5a	109 (3)
O3e—S3—C2	107.81 (16)	C6—C5—H5e	104 (3)
O3a—S3—C2	107.99 (16)	C4—C5—H5e	108 (3)
C4—S3—C2	102.81 (18)	H5a—C5—H5e	109 (4)
S1—C2—S3	112.73 (19)	C5—C6—S1	111.9 (3)
S1—C2—H2a	107 (2)	C5—C6—H6a	112 (2)
S3—C2—H2a	109 (2)	S1—C6—H6a	106 (2)
S1—C2—H2e	108 (2)	C5—C6—H6e	111 (3)
S3—C2—H2e	107 (2)	S1—C6—H6e	103 (2)
H2a—C2—H2e	113 (3)	H6a—C6—H6e	114 (3)
O1e—S1—C2—S3	172.32 (18)	O3a—S3—C4—C5	−57.4 (3)
O1a—S1—C2—S3	−59.6 (2)	C2—S3—C4—C5	57.1 (3)
C6—S1—C2—S3	56.5 (2)	S3—C4—C5—C6	−66.1 (4)
O3e—S3—C2—S1	−172.54 (18)	C4—C5—C6—S1	66.5 (4)
O3a—S3—C2—S1	59.4 (2)	O1e—S1—C6—C5	−171.4 (3)
C4—S3—C2—S1	−56.0 (2)	O1a—S1—C6—C5	57.8 (3)
O3e—S3—C4—C5	171.8 (3)	C2—S1—C6—C5	−58.2 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2a···O1a^i	0.98 (4)	2.47 (4)	3.315 (4)	143 (3)
C2—H2a···O3a^i	0.98 (4)	2.76 (4)	3.520 (5)	134 (3)
C2—H2a···O3e^ii	0.98 (4)	2.91 (4)	3.556 (4)	124 (3)
C2—H2e···O3a^ii	0.97 (4)	2.49 (4)	3.201 (4)	130 (3)
C2—H2e···O3e^iii	0.97 (4)	2.49 (4)	3.370 (4)	151 (3)
C4—H4a···O3a^i	0.99 (4)	2.46 (4)	3.329 (4)	147 (3)
C4—H4e···O3a^iv	0.94 (4)	2.70 (4)	3.462 (4)	138 (3)
C4—H4e···O3e^v	0.94 (4)	2.63 (4)	3.454 (5)	146 (3)
C5—H5e···O1a^vi	1.00 (5)	2.91 (5)	3.598 (5)	127 (3)
C5—H5e···O1e^vii	1.00 (5)	2.50 (5)	3.395 (4)	150 (4)
C6—H6a···O1a^i	0.95 (4)	2.45 (4)	3.287 (4)	147 (3)
C6—H6a···O1e^vi	0.95 (4)	2.65 (4)	3.269 (5)	124 (3)
C6—H6e···O1a^vi	0.95 (4)	2.81 (4)	3.344 (5)	116 (3)
C6—H6e···O1e^viii	0.95 (4)	2.44 (4)	3.186 (5)	135 (3)

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