Crystal structure of potassium (1S)-D-lyxit-1-yl­sulfonate monohydrate

The anion has an open-chain structure in which the S atom, the C atoms of the sugar chain and the oxygen atom of the hy­droxy­methyl group form an essentially all-trans chain. A three-dimensional bonding network exists in the crystal structure involving coordination of two crystallographically independent potassium ions by O atoms (one cation being hexa- and the other octa-coordinate, with each lying on a twofold rotation axis), and extensive inter­molecular O—H...O hydrogen bonding.

Key indicators

• Single-crystal X-ray study
• T = 140 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.018
• wR factor = 0.048
• Data-to-parameter ratio = 15.5

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT934_ALERT_3_B Number of (Iobs-Icalc)/SigmaW > 10 Outliers ....          2 Check

Alert level C
PLAT090_ALERT_3_C Poor Data / Parameter Ratio (Zmax > 18) ........       9.13 Note
PLAT222_ALERT_3_C Large Non-Solvent  H     Uiso(max)/Uiso(min) ...        6.0 Ratio

Alert level G
PLAT004_ALERT_5_G Polymeric Structure Found with Maximum Dimension          3 Info
PLAT033_ALERT_4_G Flack x Value Deviates > 2*sigma from Zero .....      0.023 Note
PLAT042_ALERT_1_G Calc. and Reported MoietyFormula Strings  Differ     Please Check
PLAT164_ALERT_4_G Nr. of Refined C-H H-Atoms in Heavy-Atom Struct.          6 Note
PLAT764_ALERT_4_G Overcomplete CIF Bond List Detected (Rep/Expd) .       1.52 Ratio
PLAT774_ALERT_1_G Suspect X-Y Bond in CIF:   K2     --  K1      ..       4.52 Ang.
PLAT774_ALERT_1_G Suspect X-Y Bond in CIF:   K2     --  K2      ..       4.99 Ang.
PLAT774_ALERT_1_G Suspect X-Y Bond in CIF:   K2     --  K2      ..       4.99 Ang.
PLAT791_ALERT_4_G The Model has Chirality at C1      (Chiral SPGR)          S Verify
PLAT791_ALERT_4_G The Model has Chirality at C2      (Chiral SPGR)          S Verify
PLAT791_ALERT_4_G The Model has Chirality at C3      (Chiral SPGR)          S Verify
PLAT791_ALERT_4_G The Model has Chirality at C4      (Chiral SPGR)          R Verify
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Th(Min) ...          3 Report
PLAT961_ALERT_5_G Dataset Contains no Negative Intensities .......     Please Check

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

   4 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
   4 ALERT type 3 Indicator that the structure quality may be low
   7 ALERT type 4 Improvement, methodology, query or suggestion
   2 ALERT type 5 Informative message, check

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Computing details

Data collection: CrysAlis PRO (Agilent, 2014); cell refinement: CrysAlis PRO (Agilent, 2014); data reduction: CrysAlis PRO (Agilent, 2014); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: ORTEP (Johnson, 1976) and ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015) and WinGX (Farrugia, 2012).

Potassium (1S,2S,3S,4R)-1,2,3,4,5-pentahydroxypentane-1-sulfonate monohydrate

Crystal data

K^+·C5H11O8S^−·H2O	Dx = 1.816 Mg m^−3
Mr = 288.31	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P21212	Cell parameters from 10753 reflections
a = 23.3536 (5) Å	θ = 3.5–32.6°
b = 9.0434 (2) Å	µ = 0.74 mm^−1
c = 4.9939 (1) Å	T = 140 K
V = 1054.69 (4) Å^3	Square prism, colourless
Z = 4	0.28 × 0.26 × 0.11 mm
F(000) = 600

Data collection

Oxford Diffraction Xcalibur 3/Sapphire3 CCD diffractometer	3062 independent reflections
Radiation source: Enhance (Mo) X-ray Source	3008 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.023
Detector resolution: 16.0050 pixels mm^-1	θmax = 30.0°, θmin = 3.5°
Thin slice φ and ω scans	h = −32→32
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2014)	k = −12→12
Tmin = 0.914, Tmax = 1.000	l = −7→7
20712 measured reflections

Refinement

Refinement on F^2	Hydrogen site location: difference Fourier map
Least-squares matrix: full	All H-atom parameters refined
R[F^2 > 2σ(F^2)] = 0.018	w = 1/[σ^2(Fo^2) + (0.0253P)^2 + 0.2102P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.048	(Δ/σ)max = 0.001
S = 1.12	Δρmax = 0.30 e Å^−3
3062 reflections	Δρmin = −0.34 e Å^−3
198 parameters	Absolute structure: Flack x determined using 1229 quotients [(I^+)-(I^-)]/[(I^+)+(I^-)] (Parsons et al., 2013)
0 restraints	Absolute structure parameter: 0.023 (11)
Primary atom site location: structure-invariant direct methods

Special details

Experimental. CrysAlisPro, Agilent Technologies, Version 1.171.36.21 Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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.

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

	x	y	z	Uiso*/Ueq
K1	0.5000	1.0000	0.67598 (9)	0.01296 (9)
K2	0.5000	0.5000	0.70830 (10)	0.01438 (9)
C1	0.37190 (6)	0.69370 (16)	0.3668 (3)	0.0102 (3)
C2	0.32071 (6)	0.69562 (16)	0.1730 (3)	0.0099 (2)
C3	0.26543 (6)	0.67837 (15)	0.3346 (3)	0.0104 (3)
C4	0.21277 (6)	0.65562 (16)	0.1567 (3)	0.0112 (3)
C5	0.15984 (6)	0.63560 (19)	0.3308 (3)	0.0150 (3)
O1	0.38531 (5)	0.55224 (13)	0.4618 (2)	0.0142 (2)
O2	0.32388 (5)	0.57866 (13)	−0.0172 (2)	0.0129 (2)
O3	0.26007 (5)	0.81265 (13)	0.4827 (3)	0.0138 (2)
O4	0.20578 (5)	0.77316 (14)	−0.0315 (2)	0.0136 (2)
O5	0.10823 (5)	0.62153 (13)	0.1783 (3)	0.0156 (2)
S1	0.43316 (2)	0.78331 (4)	0.21337 (7)	0.00910 (8)
O11	0.43680 (5)	0.73320 (13)	−0.0636 (2)	0.0145 (2)
O12	0.48337 (4)	0.74113 (13)	0.3723 (2)	0.0132 (2)
O13	0.42133 (5)	0.94196 (12)	0.2349 (3)	0.0153 (2)
O9	0.42697 (5)	0.37107 (14)	1.0868 (3)	0.0188 (2)
H1	0.3619 (8)	0.756 (2)	0.520 (4)	0.008 (4)*
H2	0.3170 (9)	0.786 (2)	0.088 (4)	0.014 (5)*
H3	0.2694 (9)	0.598 (2)	0.456 (5)	0.015 (5)*
H4	0.2190 (9)	0.573 (2)	0.044 (5)	0.017 (5)*
H5A	0.1557 (9)	0.718 (3)	0.447 (5)	0.019 (5)*
H5B	0.1647 (9)	0.553 (3)	0.444 (5)	0.019 (6)*
H1O	0.3898 (10)	0.496 (3)	0.338 (5)	0.029 (6)*
H2O	0.3515 (10)	0.585 (3)	−0.100 (5)	0.021 (6)*
H3O	0.2443 (11)	0.793 (3)	0.633 (5)	0.029 (7)*
H4O	0.2011 (12)	0.848 (3)	0.035 (6)	0.037 (8)*
H5O	0.1126 (10)	0.557 (3)	0.075 (5)	0.023 (6)*
H9A	0.4115 (12)	0.304 (3)	1.008 (7)	0.042 (8)*
H9B	0.4524 (13)	0.326 (3)	1.175 (7)	0.048 (8)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
K1	0.01062 (18)	0.01409 (18)	0.0142 (2)	−0.00037 (15)	0.000	0.000
K2	0.0152 (2)	0.01494 (19)	0.01297 (19)	0.00403 (16)	0.000	0.000
C1	0.0088 (6)	0.0117 (6)	0.0101 (6)	0.0001 (5)	0.0004 (5)	0.0014 (5)
C2	0.0087 (6)	0.0110 (6)	0.0100 (6)	0.0001 (5)	0.0000 (5)	0.0008 (5)
C3	0.0092 (6)	0.0104 (6)	0.0117 (7)	−0.0003 (5)	0.0008 (5)	0.0005 (5)
C4	0.0090 (6)	0.0116 (6)	0.0129 (7)	−0.0005 (5)	0.0004 (5)	0.0010 (6)
C5	0.0096 (6)	0.0205 (7)	0.0151 (7)	−0.0016 (5)	0.0001 (6)	0.0022 (6)
O1	0.0163 (5)	0.0135 (5)	0.0128 (5)	0.0002 (4)	−0.0024 (4)	0.0041 (4)
O2	0.0099 (5)	0.0172 (5)	0.0118 (5)	−0.0010 (4)	0.0020 (4)	−0.0032 (4)
O3	0.0140 (5)	0.0139 (5)	0.0133 (5)	−0.0014 (4)	0.0028 (4)	−0.0036 (4)
O4	0.0147 (5)	0.0146 (5)	0.0116 (5)	0.0015 (4)	−0.0002 (4)	0.0012 (4)
O5	0.0083 (5)	0.0201 (5)	0.0184 (6)	−0.0014 (4)	−0.0008 (4)	−0.0038 (5)
S1	0.00803 (14)	0.01074 (14)	0.00852 (15)	−0.00035 (11)	0.00023 (12)	0.00024 (12)
O11	0.0150 (5)	0.0200 (5)	0.0084 (5)	−0.0009 (5)	0.0011 (4)	−0.0014 (4)
O12	0.0091 (4)	0.0182 (5)	0.0124 (5)	0.0006 (4)	−0.0011 (4)	0.0013 (4)
O13	0.0160 (5)	0.0107 (4)	0.0191 (6)	−0.0006 (4)	−0.0015 (4)	0.0003 (4)
O9	0.0141 (5)	0.0159 (6)	0.0263 (6)	0.0020 (5)	−0.0060 (5)	−0.0015 (5)

Geometric parameters (Å, º)

K1—O12^i	2.8161 (12)	C2—O2	1.4233 (18)
K1—O12	2.8162 (12)	C2—C3	1.530 (2)
K1—O5^ii	2.8505 (11)	C2—H2	0.93 (2)
K1—O5^iii	2.8505 (11)	C3—O3	1.4274 (18)
K1—O13	2.9160 (12)	C3—C4	1.531 (2)
K1—O13^i	2.9160 (12)	C3—H3	0.95 (2)
K1—O11^iv	3.1131 (12)	C4—O4	1.4281 (18)
K1—O11^v	3.1131 (12)	C4—C5	1.522 (2)
K1—O13^iv	3.3824 (13)	C4—H4	0.95 (2)
K1—O13^v	3.3824 (13)	C5—O5	1.4313 (18)
K1—S1^i	3.4078 (5)	C5—H5A	0.95 (2)
K1—S1	3.4079 (5)	C5—H5B	0.94 (2)
K2—O12	2.7787 (12)	O1—H1O	0.80 (3)
K2—O12^vi	2.7787 (12)	O2—H2O	0.77 (3)
K2—O9	2.8002 (14)	O3—H3O	0.85 (3)
K2—O9^vi	2.8003 (14)	O4—H4O	0.76 (3)
K2—O11^v	2.8149 (12)	O5—K1^x	2.8505 (11)
K2—O11^vii	2.8149 (12)	O5—H5O	0.78 (3)
K2—O1	2.9854 (12)	S1—O11	1.4579 (11)
K2—O1^vi	2.9855 (12)	S1—O13	1.4650 (11)
K2—K1^viii	4.5246 (1)	S1—O12	1.4665 (11)
K2—K2^v	4.9939 (1)	S1—K1^ix	3.6713 (5)
K2—K2^ix	4.9939 (1)	O11—K2^ix	2.8149 (12)
K2—H9B	3.02 (3)	O11—K1^ix	3.1131 (12)
C1—O1	1.3998 (18)	O13—K1^ix	3.3824 (13)
C1—C2	1.538 (2)	O9—H9A	0.81 (3)
C1—S1	1.8141 (15)	O9—H9B	0.84 (3)
C1—H1	0.98 (2)
O12^i—K1—O12	114.84 (5)	O9^vi—K2—K1^viii	116.12 (3)
O12^i—K1—O5^ii	109.61 (3)	O11^v—K2—K1^viii	139.74 (2)
O12—K1—O5^ii	86.51 (3)	O11^vii—K2—K1^viii	42.75 (2)
O12^i—K1—O5^iii	86.51 (3)	O1—K2—K1^viii	98.25 (2)
O12—K1—O5^iii	109.61 (3)	O1^vi—K2—K1^viii	80.05 (2)
O5^ii—K1—O5^iii	150.43 (6)	K1—K2—K1^viii	175.911 (17)
O12^i—K1—O13	80.20 (3)	O12—K2—K2^v	127.14 (3)
O12—K1—O13	49.96 (3)	O12^vi—K2—K2^v	127.14 (3)
O5^ii—K1—O13	133.00 (4)	O9—K2—K2^v	47.55 (3)
O5^iii—K1—O13	72.75 (3)	O9^vi—K2—K2^v	47.55 (3)
O12^i—K1—O13^i	49.96 (3)	O11^v—K2—K2^v	66.13 (2)
O12—K1—O13^i	80.20 (3)	O11^vii—K2—K2^v	66.13 (2)
O5^ii—K1—O13^i	72.76 (3)	O1—K2—K2^v	114.35 (3)
O5^iii—K1—O13^i	133.00 (4)	O1^vi—K2—K2^v	114.35 (3)
O13—K1—O13^i	81.87 (5)	K1—K2—K2^v	92.044 (9)
O12^i—K1—O11^iv	61.01 (3)	K1^viii—K2—K2^v	92.044 (9)
O12—K1—O11^iv	159.17 (3)	O12—K2—K2^ix	52.86 (3)
O5^ii—K1—O11^iv	76.81 (3)	O12^vi—K2—K2^ix	52.86 (3)
O5^iii—K1—O11^iv	90.86 (3)	O9—K2—K2^ix	132.45 (3)
O13—K1—O11^iv	138.92 (3)	O9^vi—K2—K2^ix	132.45 (3)
O13^i—K1—O11^iv	82.96 (3)	O11^v—K2—K2^ix	113.87 (2)
O12^i—K1—O11^v	159.16 (3)	O11^vii—K2—K2^ix	113.87 (2)
O12—K1—O11^v	61.01 (3)	O1—K2—K2^ix	65.65 (3)
O5^ii—K1—O11^v	90.86 (3)	O1^vi—K2—K2^ix	65.65 (3)
O5^iii—K1—O11^v	76.81 (3)	K1—K2—K2^ix	87.956 (9)
O13—K1—O11^v	82.96 (3)	K1^viii—K2—K2^ix	87.956 (9)
O13^i—K1—O11^v	138.92 (3)	K2^v—K2—K2^ix	180.0
O11^iv—K1—O11^v	130.61 (4)	O12—K2—H9B	145.3 (6)
O12^i—K1—O13^iv	103.91 (3)	O12^vi—K2—H9B	96.3 (6)
O12—K1—O13^iv	130.41 (3)	O9—K2—H9B	16.1 (6)
O5^ii—K1—O13^iv	50.78 (3)	O9^vi—K2—H9B	85.4 (6)
O5^iii—K1—O13^iv	102.19 (3)	O11^v—K2—H9B	83.3 (6)
O13—K1—O13^iv	173.46 (3)	O11^vii—K2—H9B	59.4 (6)
O13^i—K1—O13^iv	104.67 (3)	O1—K2—H9B	94.0 (6)
O11^iv—K1—O13^iv	43.74 (3)	O1^vi—K2—H9B	124.5 (6)
O11^v—K1—O13^iv	91.89 (3)	K1—K2—H9B	123.1 (6)
O12^i—K1—O13^v	130.41 (3)	K1^viii—K2—H9B	60.6 (6)
O12—K1—O13^v	103.91 (3)	K2^v—K2—H9B	39.5 (6)
O5^ii—K1—O13^v	102.19 (3)	K2^ix—K2—H9B	140.5 (6)
O5^iii—K1—O13^v	50.78 (3)	O1—C1—C2	113.41 (12)
O13—K1—O13^v	104.67 (3)	O1—C1—S1	112.02 (10)
O13^i—K1—O13^v	173.46 (3)	C2—C1—S1	110.00 (10)
O11^iv—K1—O13^v	91.89 (3)	O1—C1—H1	108.2 (12)
O11^v—K1—O13^v	43.74 (3)	C2—C1—H1	107.6 (11)
O13^iv—K1—O13^v	68.79 (4)	S1—C1—H1	105.2 (11)
O12^i—K1—S1^i	25.01 (2)	O2—C2—C3	108.66 (11)
O12—K1—S1^i	100.14 (3)	O2—C2—C1	111.77 (11)
O5^ii—K1—S1^i	89.35 (3)	C3—C2—C1	108.82 (12)
O5^iii—K1—S1^i	110.94 (3)	O2—C2—H2	110.9 (13)
O13—K1—S1^i	83.10 (3)	C3—C2—H2	104.6 (13)
O13^i—K1—S1^i	25.29 (2)	C1—C2—H2	111.7 (13)
O11^iv—K1—S1^i	67.69 (2)	O3—C3—C2	105.10 (11)
O11^v—K1—S1^i	161.09 (2)	O3—C3—C4	110.15 (12)
O13^iv—K1—S1^i	102.79 (2)	C2—C3—C4	112.67 (12)
O13^v—K1—S1^i	153.82 (2)	O3—C3—H3	109.2 (14)
O12^i—K1—S1	100.14 (3)	C2—C3—H3	109.4 (14)
O12—K1—S1	25.01 (2)	C4—C3—H3	110.2 (13)
O5^ii—K1—S1	110.94 (3)	O4—C4—C5	111.81 (12)
O5^iii—K1—S1	89.34 (3)	O4—C4—C3	111.94 (12)
O13—K1—S1	25.29 (2)	C5—C4—C3	109.69 (12)
O13^i—K1—S1	83.11 (3)	O4—C4—H4	102.4 (14)
O11^iv—K1—S1	161.09 (2)	C5—C4—H4	111.7 (14)
O11^v—K1—S1	67.69 (2)	C3—C4—H4	109.1 (13)
O13^iv—K1—S1	153.82 (2)	O5—C5—C4	113.00 (13)
O13^v—K1—S1	102.79 (2)	O5—C5—H5A	108.0 (13)
S1^i—K1—S1	94.639 (16)	C4—C5—H5A	109.8 (13)
O12—K2—O12^vi	105.71 (5)	O5—C5—H5B	110.5 (13)
O12—K2—O9	130.48 (3)	C4—C5—H5B	109.7 (13)
O12^vi—K2—O9	99.55 (3)	H5A—C5—H5B	105.5 (19)
O12—K2—O9^vi	99.55 (3)	C1—O1—K2	119.01 (9)
O12^vi—K2—O9^vi	130.48 (3)	C1—O1—H1O	110.1 (19)
O9—K2—O9^vi	95.09 (6)	K2—O1—H1O	95.8 (18)
O12—K2—O11^v	65.36 (3)	C2—O2—H2O	110.5 (18)
O12^vi—K2—O11^v	154.90 (3)	C3—O3—H3O	108.4 (18)
O9—K2—O11^v	73.70 (4)	C4—O4—H4O	113 (2)
O9^vi—K2—O11^v	74.59 (4)	C5—O5—K1^x	130.19 (10)
O12—K2—O11^vii	154.90 (3)	C5—O5—H5O	107.9 (17)
O12^vi—K2—O11^vii	65.36 (3)	K1^x—O5—H5O	89.8 (17)
O9—K2—O11^vii	74.59 (4)	O11—S1—O13	112.64 (7)
O9^vi—K2—O11^vii	73.70 (4)	O11—S1—O12	112.71 (7)
O11^v—K2—O11^vii	132.26 (5)	O13—S1—O12	111.46 (7)
O12—K2—O1	60.09 (3)	O11—S1—C1	107.93 (7)
O12^vi—K2—O1	90.03 (3)	O13—S1—C1	104.94 (7)
O9—K2—O1	78.33 (4)	O12—S1—C1	106.60 (7)
O9^vi—K2—O1	139.37 (4)	O11—S1—K1	142.67 (5)
O11^v—K2—O1	65.03 (3)	O13—S1—K1	58.23 (5)
O11^vii—K2—O1	139.10 (3)	O12—S1—K1	54.30 (5)
O12—K2—O1^vi	90.03 (3)	C1—S1—K1	109.38 (5)
O12^vi—K2—O1^vi	60.10 (3)	O11—S1—K1^ix	56.47 (5)
O9—K2—O1^vi	139.37 (4)	O13—S1—K1^ix	67.11 (5)
O9^vi—K2—O1^vi	78.33 (4)	O12—S1—K1^ix	101.22 (5)
O11^v—K2—O1^vi	139.10 (3)	C1—S1—K1^ix	151.95 (5)
O11^vii—K2—O1^vi	65.03 (3)	K1—S1—K1^ix	89.650 (8)
O1—K2—O1^vi	131.29 (5)	S1—O11—K2^ix	130.34 (7)
O12—K2—K1	36.31 (2)	S1—O11—K1^ix	100.55 (6)
O12^vi—K2—K1	139.71 (3)	K2^ix—O11—K1^ix	99.38 (3)
O9—K2—K1	116.12 (3)	S1—O12—K2	130.00 (6)
O9^vi—K2—K1	66.92 (3)	S1—O12—K1	100.69 (6)
O11^v—K2—K1	42.75 (2)	K2—O12—K1	107.94 (4)
O11^vii—K2—K1	139.74 (2)	S1—O13—K1	96.48 (6)
O1—K2—K1	80.05 (2)	S1—O13—K1^ix	89.37 (5)
O1^vi—K2—K1	98.25 (2)	K1—O13—K1^ix	104.67 (3)
O12—K2—K1^viii	139.71 (3)	K2—O9—H9A	105 (2)
O12^vi—K2—K1^viii	36.31 (2)	K2—O9—H9B	97 (2)
O9—K2—K1^viii	66.92 (3)	H9A—O9—H9B	102 (3)
O1—C1—C2—O2	−44.09 (16)	O13—S1—O11—K2^ix	150.63 (7)
S1—C1—C2—O2	82.24 (13)	O12—S1—O11—K2^ix	23.46 (10)
O1—C1—C2—C3	75.92 (15)	C1—S1—O11—K2^ix	−93.99 (9)
S1—C1—C2—C3	−157.75 (10)	K1—S1—O11—K2^ix	83.82 (10)
O2—C2—C3—O3	−169.41 (11)	K1^ix—S1—O11—K2^ix	112.07 (8)
C1—C2—C3—O3	68.67 (14)	O13—S1—O11—K1^ix	38.57 (7)
O2—C2—C3—C4	−49.45 (15)	O12—S1—O11—K1^ix	−88.61 (6)
C1—C2—C3—C4	−171.36 (11)	C1—S1—O11—K1^ix	153.94 (5)
O3—C3—C4—O4	60.33 (15)	K1—S1—O11—K1^ix	−28.25 (9)
C2—C3—C4—O4	−56.67 (16)	O11—S1—O12—K2	−95.90 (9)
O3—C3—C4—C5	−64.38 (15)	O13—S1—O12—K2	136.30 (8)
C2—C3—C4—C5	178.61 (12)	C1—S1—O12—K2	22.33 (10)
O4—C4—C5—O5	52.08 (17)	K1—S1—O12—K2	124.57 (9)
C3—C4—C5—O5	176.87 (12)	K1^ix—S1—O12—K2	−154.07 (6)
C2—C1—O1—K2	162.60 (8)	O11—S1—O12—K1	139.53 (6)
S1—C1—O1—K2	37.34 (13)	O13—S1—O12—K1	11.73 (7)
C4—C5—O5—K1^x	159.72 (9)	C1—S1—O12—K1	−102.24 (6)
O1—C1—S1—O11	84.07 (12)	K1^ix—S1—O12—K1	81.36 (3)
C2—C1—S1—O11	−43.04 (11)	O11—S1—O13—K1	−139.03 (6)
O1—C1—S1—O13	−155.59 (11)	O12—S1—O13—K1	−11.20 (7)
C2—C1—S1—O13	77.30 (11)	C1—S1—O13—K1	103.80 (6)
O1—C1—S1—O12	−37.26 (12)	K1^ix—S1—O13—K1	−104.69 (4)
C2—C1—S1—O12	−164.36 (10)	O11—S1—O13—K1^ix	−34.34 (6)
O1—C1—S1—K1	−94.52 (10)	O12—S1—O13—K1^ix	93.50 (6)
C2—C1—S1—K1	138.37 (8)	C1—S1—O13—K1^ix	−151.50 (5)
O1—C1—S1—K1^ix	135.22 (9)	K1—S1—O13—K1^ix	104.69 (4)
C2—C1—S1—K1^ix	8.11 (18)

Symmetry codes: (i) −x+1, −y+2, z; (ii) x+1/2, −y+3/2, −z+1; (iii) −x+1/2, y+1/2, −z+1; (iv) −x+1, −y+2, z+1; (v) x, y, z+1; (vi) −x+1, −y+1, z; (vii) −x+1, −y+1, z+1; (viii) x, y−1, z; (ix) x, y, z−1; (x) −x+1/2, y−1/2, −z+1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O···O9^ix	0.80 (3)	1.90 (3)	2.6716 (19)	160 (2)
O2—H2O···O1^ix	0.77 (3)	2.35 (3)	2.9810 (17)	141 (2)
O2—H2O···O11	0.77 (3)	2.41 (2)	2.9935 (16)	134 (2)
O3—H3O···O4^v	0.85 (3)	1.91 (3)	2.7609 (17)	173 (3)
O4—H4O···O2^xi	0.76 (3)	2.17 (3)	2.8586 (17)	151 (3)
O5—H5O···O13^xii	0.78 (3)	2.03 (3)	2.7152 (17)	146 (2)
O9—H9A···O5^x	0.81 (3)	1.95 (3)	2.7426 (18)	167 (3)
O9—H9B···O12^vii	0.84 (3)	1.90 (3)	2.7289 (17)	170 (3)

Symmetry codes: (v) x, y, z+1; (vii) −x+1, −y+1, z+1; (ix) x, y, z−1; (x) −x+1/2, y−1/2, −z+1; (xi) −x+1/2, y+1/2, −z; (xii) −x+1/2, y−1/2, −z.