Crystal structure of dilithium biphenyl-4,4′-di­sulfonate dihydrate

The asymmetric unit of the title compound consists of an Li ion, half of the diphenyl-4,4-di­sulfonate ligand, and a water mol­ecule. The Li ion exhibits a four-coordinate tetra­hedral geometry with three oxygen atoms of the Bph(SO₃⁻)₂ ligands and a water mol­ecule. The tetra­hedral LiO₄ units, which are inter­connected by biphenyl moieties, form a layer structure parallel to (100). These layers are further connected by hydrogen-bonding inter­actions to yield a three-dimensional network.

Key indicators

Structure: I

• Single-crystal X-ray study
• T = 286 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.061
• wR factor = 0.159
• Data-to-parameter ratio = 12.5

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT042_ALERT_1_C Calc. and Reported MoietyFormula Strings  Differ     Please Check
              Calc: C6 H6 Li O4 S
              Rep.: C12 H12 Li2 O8 S2
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.64 Report
PLAT241_ALERT_2_C High   'MainMol' Ueq as Compared to Neighbors of         O1 Check
PLAT242_ALERT_2_C Low    'MainMol' Ueq as Compared to Neighbors of         C1 Check
PLAT242_ALERT_2_C Low    'MainMol' Ueq as Compared to Neighbors of         C4 Check
PLAT242_ALERT_2_C Low    'MainMol' Ueq as Compared to Neighbors of        Li1 Check
PLAT350_ALERT_3_C Short  C-H (X0.96,N1.08A)  C6       - H6       .       0.81 Ang.
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      8.503 Check
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600         23 Report
                4  0  0,   5  0  0,   5  2  0,   6  0  0,   7  0  0,   8  0  0,
                9  0  0,  10  0  0,  11  0  0,  12  0  0,  13  0  0,  13  2  0,
               14  0  0,  15  0  0,  16  0  0,  16  2  0,  17  0  0,  17  2  0,
               18  0  0,  10  0  4,   9  0  6,  11  0  6,  13  0  6,
PLAT934_ALERT_3_C Number of (Iobs-Icalc)/Sigma(W) > 10 Outliers ..          1 Check
                8  0  4,

Alert level G
PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite          3 Note
PLAT004_ALERT_5_G Polymeric Structure Found with Maximum Dimension          2 Info
PLAT045_ALERT_1_G Calculated and Reported Z Differ by a Factor ...          2 Check
PLAT172_ALERT_4_G The CIF-Embedded .res File Contains DFIX Records          2 Report
PLAT173_ALERT_4_G The CIF-Embedded .res File Contains DANG Records          1 Report
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............          3 Note
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          2 Note
                1  0  0,   2  0  0,
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600          5 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          4 Info
PLAT992_ALERT_5_G Repd & Actual _reflns_number_gt Values Differ by          2 Check

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

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   7 ALERT type 2 Indicator that the structure model may be wrong or deficient
   6 ALERT type 3 Indicator that the structure quality may be low
   3 ALERT type 4 Improvement, methodology, query or suggestion
   2 ALERT type 5 Informative message, check


checkCIF publication errors

Alert level A
PUBL002_ALERT_1_A  The contact author's address is missing,
            _publ_contact_author_address.

   1 ALERT level A = Data missing that is essential or data in wrong format
   0 ALERT level G = General alerts. Data that may be required is missing
# start Validation Reply Form
_vrf_PUBL002_GLOBAL
;
PROBLEM: The contact author's address is missing,
RESPONSE: ...
;
# end Validation Reply Form 

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Reference check results

The following references were not checked in detail as they were not recognized as references to journal articles

Rigaku (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan. [software reference?]

Rigaku (1995). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan. [software reference?]

Rigaku (2016). CrystalStructure. Rigaku Corporation, Tokyo, Japan. [software reference?]

The following references may be incorrectly formatted

Albat, M. & Stock, N. (2016). IUCrData, 1, x160039.
[Missing final page numbers?]

Armand, M., Grugeon, S., Vezin, H., Laruelle, S., Ribi\'ere, P., Poizot, P. & Tarascon, J. M. (2009). Nat. Mater. 2009 8, 120--125.
[Missing final page numbers?]

Ogihara, N., Ohba, N. & Kishida, Y. (2017). Sci. Adv. 3, e1603103.
[Unrecognized journal title. Missing final page numbers?]

Ozawa, Y., Ogihara, N., Hasegawa, M., Hiruta, O., Ohba, N. & Kishida, Y. (2018). Commun. Chem. 1, 65.
[Unrecognized journal title. Missing final page numbers?]

The following references do not appear to be cited

Rigaku (2016). CrystalStructure. Rigaku Corporation, Tokyo, Japan.

Sheldrick, G. M. (2015a). Acta Cryst. A71, 3--8.

Sheldrick, G. M. (2015b). Acta Cryst. C71, 3--8.

Citation comments

4 reference(s) in data_global _publ_body_contents should be checked as possibly cited ambiguously (or simply identified with less confidence)

1 date found in data_global _publ_body_contents that could be part of a citation but not found in reference list: 2023

2 reference(s) in data_I _exptl_absorpt_process_details should be checked as possibly cited ambiguously (or simply identified with less confidence)

1 date found in data_I _computing_structure_solution that could be part of a citation but not found in reference list: 2014

1 date found in data_I _computing_structure_refinement that could be part of a citation but not found in reference list: 2008

1 date found in data_I _computing_publication_material that could be part of a citation but not found in reference list: 2019

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Computing details

µ-Biphenyl-4,4'-disulfonato-bis(aqualithium)

Crystal data

[Li2(C12H8O6S2)(H2O)2]	F(000) = 372.00
Mr = 362.22	Dx = 1.618 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71075 Å
a = 15.8584 (11) Å	Cell parameters from 17604 reflections
b = 5.3693 (4) Å	θ = 3.2–27.6°
c = 8.8636 (6) Å	µ = 0.40 mm^−1
β = 99.994 (7)°	T = 286 K
V = 743.27 (9) Å^3	Block, colorless
Z = 2	0.50 × 0.40 × 0.20 mm

Data collection

Rigaku R-AXIS RAPID diffractometer	1490 reflections with F^2 > 2.0σ(F^2)
Detector resolution: 10.000 pixels mm^-1	Rint = 0.067
ω scans	θmax = 27.5°, θmin = 3.9°
Absorption correction: multi-scan (ABSCOR; Rigaku, 1995)	h = −20→20
Tmin = 0.213, Tmax = 0.924	k = −6→6
9858 measured reflections	l = −11→11
1666 independent reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.061	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.159	All H-atom parameters refined
S = 1.12	w = 1/[σ^2(Fo^2) + (0.0948P)^2 + 0.3642P] where P = (Fo^2 + 2Fc^2)/3
1666 reflections	(Δ/σ)max < 0.001
133 parameters	Δρmax = 0.74 e Å^−3
3 restraints	Δρmin = −0.28 e Å^−3
Primary atom site location: structure-invariant direct methods

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.

Refinement. Refinement was performed using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F². R-factor (gt) are based on F. The threshold expression of F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).

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

	x	y	z	Uiso*/Ueq
S1	0.67846 (4)	0.56370 (10)	0.59448 (6)	0.0341 (3)
O1	0.66681 (15)	0.8238 (3)	0.6295 (3)	0.0550 (6)
O2	0.62416 (15)	0.4887 (5)	0.4532 (2)	0.0566 (6)
O3	0.67041 (13)	0.4012 (4)	0.7215 (2)	0.0451 (5)
O4	0.49748 (14)	1.0921 (5)	0.6579 (3)	0.0587 (6)
C1	0.78551 (17)	0.5384 (4)	0.5648 (3)	0.0346 (5)
C2	0.81715 (19)	0.7143 (6)	0.4756 (4)	0.0566 (8)
C3	0.90075 (19)	0.6964 (6)	0.4499 (4)	0.0588 (9)
C4	0.95484 (15)	0.5075 (4)	0.5137 (3)	0.0354 (5)
C5	0.9221 (2)	0.3349 (6)	0.6046 (5)	0.0628 (9)
C6	0.8381 (2)	0.3489 (6)	0.6297 (5)	0.0608 (9)
Li1	0.6195 (3)	1.0777 (8)	0.7388 (5)	0.0413 (9)
H1	0.464 (3)	0.986 (9)	0.696 (7)	0.13 (2)*
H2	0.778 (3)	0.874 (10)	0.441 (5)	0.083 (13)*
H3	0.916 (3)	0.789 (10)	0.375 (6)	0.099 (16)*
H4	0.462 (3)	1.197 (9)	0.600 (6)	0.12 (2)*
H5	0.954 (3)	0.196 (9)	0.644 (5)	0.078 (13)*
H6	0.823 (3)	0.262 (9)	0.695 (6)	0.096 (16)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0333 (4)	0.0345 (4)	0.0359 (4)	0.0043 (2)	0.0093 (2)	−0.0016 (2)
O1	0.0641 (13)	0.0359 (11)	0.0724 (13)	0.0116 (9)	0.0324 (11)	0.0000 (9)
O2	0.0377 (11)	0.0905 (17)	0.0413 (10)	0.0008 (10)	0.0057 (9)	−0.0115 (10)
O3	0.0481 (11)	0.0404 (9)	0.0485 (10)	−0.0001 (8)	0.0131 (8)	0.0050 (8)
O4	0.0396 (12)	0.0691 (14)	0.0666 (14)	0.0048 (10)	0.0073 (10)	0.0160 (11)
C1	0.0334 (12)	0.0316 (11)	0.0386 (11)	0.0022 (8)	0.0060 (9)	−0.0036 (8)
C2	0.0352 (13)	0.0581 (17)	0.077 (2)	0.0112 (12)	0.0120 (13)	0.0322 (15)
C3	0.0356 (14)	0.0630 (19)	0.079 (2)	0.0077 (12)	0.0137 (14)	0.0355 (16)
C4	0.0302 (13)	0.0337 (11)	0.0414 (12)	0.0007 (8)	0.0042 (10)	−0.0033 (9)
C5	0.0479 (17)	0.0465 (15)	0.100 (3)	0.0186 (13)	0.0298 (17)	0.0301 (17)
C6	0.0489 (16)	0.0460 (15)	0.095 (2)	0.0149 (13)	0.0333 (17)	0.0300 (17)
Li1	0.041 (2)	0.041 (2)	0.043 (2)	0.0029 (17)	0.0106 (18)	0.0036 (16)

Geometric parameters (Å, º)

S1—O3	1.4472 (19)	C1—C2	1.381 (4)
S1—O2	1.448 (2)	C2—C3	1.387 (4)
S1—O1	1.4492 (19)	C2—H2	1.07 (5)
S1—C1	1.768 (3)	C3—C4	1.384 (4)
O1—Li1	1.901 (5)	C3—H3	0.90 (5)
O2—Li1^i	1.922 (5)	C4—C5	1.387 (4)
O3—Li1^ii	1.933 (5)	C4—C4^iii	1.496 (5)
O4—Li1	1.944 (5)	C5—C6	1.390 (4)
O4—H1	0.88 (2)	C5—H5	0.94 (5)
O4—H4	0.89 (2)	C6—H6	0.81 (5)
C1—C6	1.377 (4)
O3—S1—O2	112.66 (14)	C4—C3—C2	121.8 (3)
O3—S1—O1	112.48 (12)	C4—C3—H3	119 (3)
O2—S1—O1	112.00 (15)	C2—C3—H3	118 (3)
O3—S1—C1	106.61 (11)	C3—C4—C5	117.3 (2)
O2—S1—C1	107.01 (12)	C3—C4—C4^iii	121.1 (3)
O1—S1—C1	105.51 (12)	C5—C4—C4^iii	121.6 (3)
S1—O1—Li1	151.24 (19)	C4—C5—C6	121.5 (3)
S1—O2—Li1^i	145.2 (2)	C4—C5—H5	121 (3)
S1—O3—Li1^ii	134.28 (19)	C6—C5—H5	118 (3)
Li1—O4—H1	117 (4)	C1—C6—C5	120.1 (3)
Li1—O4—H4	136 (4)	C1—C6—H6	119 (4)
H1—O4—H4	106 (4)	C5—C6—H6	120 (4)
C6—C1—C2	119.4 (3)	O1—Li1—O2^iv	114.8 (2)
C6—C1—S1	121.5 (2)	O1—Li1—O3^v	113.3 (2)
C2—C1—S1	119.09 (19)	O2^iv—Li1—O3^v	107.5 (2)
C1—C2—C3	119.9 (3)	O1—Li1—O4	107.2 (3)
C1—C2—H2	117 (2)	O2^iv—Li1—O4	103.7 (2)
C3—C2—H2	122 (2)	O3^v—Li1—O4	109.8 (2)
O3—S1—O1—Li1	−27.3 (5)	O2—S1—C1—C2	74.3 (3)
O2—S1—O1—Li1	100.8 (5)	O1—S1—C1—C2	−45.2 (3)
C1—S1—O1—Li1	−143.1 (4)	C6—C1—C2—C3	1.1 (5)
O3—S1—O2—Li1^i	−131.3 (4)	S1—C1—C2—C3	−179.5 (3)
O1—S1—O2—Li1^i	100.7 (4)	C1—C2—C3—C4	−1.1 (6)
C1—S1—O2—Li1^i	−14.4 (4)	C2—C3—C4—C5	0.2 (5)
O2—S1—O3—Li1^ii	12.8 (3)	C2—C3—C4—C4^iii	−179.3 (3)
O1—S1—O3—Li1^ii	140.6 (3)	C3—C4—C5—C6	0.6 (6)
C1—S1—O3—Li1^ii	−104.2 (3)	C4^iii—C4—C5—C6	−179.8 (4)
O3—S1—C1—C6	14.5 (3)	C2—C1—C6—C5	−0.3 (6)
O2—S1—C1—C6	−106.3 (3)	S1—C1—C6—C5	−179.7 (3)
O1—S1—C1—C6	134.3 (3)	C4—C5—C6—C1	−0.6 (6)
O3—S1—C1—C2	−165.0 (2)

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4···O2^vi	0.89 (5)	2.17 (5)	3.016 (3)	157 (5)
O4—H1···O3^vii	2.41 (5)	3.21 (1)	0.89 (5)	149 (4)
O4—H1···O4^viii	2.50 (5)	3.14 (1)	0.89 (5)	129 (4)

Symmetry codes: (vi) −x+1, −y+2, −z+1; (vii) −x+1, y+1/2, −z+3/2; (viii) −x+1, y−1/2, −z+3/2.