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The title compound, C14H28O2S4, possesses a crystallograph­ically imposed inversion centre and has two methine C atoms linked to methoxy­methyl functional groups. It is in the exodentate conformation, with the four S atoms lying on the edges of the `rectangular' macrocycle. The lone pairs of electrons on the S atoms point outwards from the macrocyclic cavity and the S atoms are bridged alternately by one-carbon and four-carbon moieties.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803029283/wn6208sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803029283/wn6208Isup2.hkl
Contains datablock I

CCDC reference: 234838

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • R factor = 0.049
  • wR factor = 0.143
  • Data-to-parameter ratio = 16.3

checkCIF/PLATON results

No syntax errors found



Alert level C REFLT03_ALERT_3_C Reflection count < 95% complete From the CIF: _diffrn_reflns_theta_max 25.21 From the CIF: _diffrn_reflns_theta_full 0.00 From the CIF: _reflns_number_total 1497 TEST2: Reflns within _diffrn_reflns_theta_max Count of symmetry unique reflns 1629 Completeness (_total/calc) 91.90% PLAT022_ALERT_3_C Ratio Unique / Expected Reflections too Low .... 0.92
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 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 0 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

Computing details top

Data collection: XSCANS (Siemens, 1996); cell refinement: XSCANS; data reduction: SHELXTL (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

(I) top
Crystal data top
C14H28O2S4F(000) = 384
Mr = 356.64Dx = 1.307 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 25 reflections
a = 10.5512 (10) Åθ = 12–18°
b = 10.4538 (12) ŵ = 0.52 mm1
c = 8.2152 (10) ÅT = 293 K
β = 91.061 (10)°Plate, colourless
V = 905.98 (17) Å30.40 × 0.20 × 0.10 mm
Z = 2
Data collection top
Siemens P4
diffractometer
Rint = 0.052
Radiation source: fine-focus sealed tubeθmax = 25.2°, θmin = 1.9°
Graphite monochromatorh = 1212
non–profiled w scansk = 012
1619 measured reflectionsl = 09
1497 independent reflections2 standard reflections every 50 reflections
1262 reflections with I > 2σ(I) intensity decay: 1%
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.050H-atom parameters constrained
wR(F2) = 0.143 w = 1/[σ2(Fo2) + (0.1005P)2 + 0.1736P]
where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max < 0.001
1497 reflectionsΔρmax = 0.29 e Å3
92 parametersΔρmin = 0.43 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.13 (2)
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
S10.20992 (7)0.03165 (7)0.26140 (9)0.0472 (3)
S20.27180 (7)0.01049 (7)0.62716 (9)0.0481 (3)
O10.48637 (17)0.2012 (2)0.5060 (3)0.0608 (6)
C30.0513 (3)0.1625 (3)0.1723 (3)0.0544 (8)
H3A0.03010.25230.18380.065*
H3B0.07990.14980.06190.065*
C20.1603 (3)0.1321 (3)0.2887 (4)0.0499 (7)
H2A0.23080.18910.26840.060*
H2B0.13390.14490.40000.060*
C60.3746 (2)0.1881 (3)0.4115 (4)0.0477 (7)
H6A0.39150.20790.29860.057*
H6B0.31080.24710.44960.057*
C40.0689 (3)0.0840 (3)0.1952 (3)0.0503 (7)
H4A0.04770.00620.19020.060*
H4B0.12790.10230.10630.060*
C10.3267 (2)0.0511 (3)0.4256 (3)0.0433 (6)
H10.39800.00570.40200.052*
C50.1329 (3)0.1110 (3)0.3546 (3)0.0490 (7)
H5A0.07430.09420.44440.059*
H5B0.15750.20030.35910.059*
C70.5381 (3)0.3247 (4)0.4917 (5)0.0754 (11)
H7A0.61380.33080.55790.113*
H7B0.47760.38680.52750.113*
H7C0.55810.34090.38010.113*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0578 (5)0.0468 (5)0.0370 (5)0.0069 (3)0.0034 (3)0.0067 (3)
S20.0561 (5)0.0504 (5)0.0377 (6)0.0003 (3)0.0037 (3)0.0116 (3)
O10.0546 (11)0.0474 (11)0.0797 (16)0.0066 (9)0.0170 (11)0.0058 (11)
C30.0729 (17)0.0526 (15)0.0381 (17)0.0120 (14)0.0116 (13)0.0118 (13)
C20.0593 (15)0.0442 (14)0.0465 (17)0.0003 (12)0.0078 (12)0.0025 (12)
C60.0471 (12)0.0488 (15)0.0471 (16)0.0018 (11)0.0029 (11)0.0095 (12)
C40.0604 (15)0.0599 (17)0.0303 (15)0.0155 (13)0.0031 (11)0.0008 (13)
C10.0441 (12)0.0451 (13)0.0408 (16)0.0032 (10)0.0009 (10)0.0012 (11)
C50.0638 (15)0.0491 (15)0.0341 (15)0.0006 (12)0.0052 (11)0.0040 (12)
C70.0740 (19)0.061 (2)0.091 (3)0.0213 (16)0.0032 (19)0.0064 (18)
Geometric parameters (Å, º) top
S1—C21.805 (3)C6—H6A0.9700
S1—C11.821 (3)C6—H6B0.9700
S2—C5i1.812 (3)C4—C51.511 (4)
S2—C11.815 (3)C4—H4A0.9700
O1—C61.406 (3)C4—H4B0.9700
O1—C71.407 (4)C1—H10.9800
C3—C21.517 (4)C5—S2i1.812 (3)
C3—C41.525 (4)C5—H5A0.9700
C3—H3A0.9700C5—H5B0.9700
C3—H3B0.9700C7—H7A0.9600
C2—H2A0.9700C7—H7B0.9600
C2—H2B0.9700C7—H7C0.9600
C6—C11.524 (4)
C2—S1—C1101.97 (13)C3—C4—H4A109.0
C5i—S2—C1102.26 (12)C5—C4—H4B109.0
C6—O1—C7111.5 (2)C3—C4—H4B109.0
C2—C3—C4115.6 (2)H4A—C4—H4B107.8
C2—C3—H3A108.4C6—C1—S2113.7 (2)
C4—C3—H3A108.4C6—C1—S1105.64 (19)
C2—C3—H3B108.4S2—C1—S1115.24 (13)
C4—C3—H3B108.4C6—C1—H1107.3
H3A—C3—H3B107.4S2—C1—H1107.3
C3—C2—S1109.8 (2)S1—C1—H1107.3
C3—C2—H2A109.7C4—C5—S2i109.8 (2)
S1—C2—H2A109.7C4—C5—H5A109.7
C3—C2—H2B109.7S2i—C5—H5A109.7
S1—C2—H2B109.7C4—C5—H5B109.7
H2A—C2—H2B108.2S2i—C5—H5B109.7
O1—C6—C1109.0 (2)H5A—C5—H5B108.2
O1—C6—H6A109.9O1—C7—H7A109.5
C1—C6—H6A109.9O1—C7—H7B109.5
O1—C6—H6B109.9H7A—C7—H7B109.5
C1—C6—H6B109.9O1—C7—H7C109.5
H6A—C6—H6B108.3H7A—C7—H7C109.5
C5—C4—C3113.1 (2)H7B—C7—H7C109.5
C5—C4—H4A109.0
C4—C3—C2—S162.0 (3)C5i—S2—C1—C666.7 (2)
C1—S1—C2—C3173.99 (19)C5i—S2—C1—S155.40 (18)
C7—O1—C6—C1177.4 (3)C2—S1—C1—C6179.82 (18)
C2—C3—C4—C566.5 (3)C2—S1—C1—S253.85 (18)
O1—C6—C1—S267.4 (2)C3—C4—C5—S2i178.50 (19)
O1—C6—C1—S1165.31 (18)
Symmetry code: (i) x, y, z+1.
 

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