Layered triaqua­(phenyl­selenona­to)lithium(I)

The title compound, [Li(C₆H₅O₃Se)(H₂O)₃], shows an extensive hydrogen-bonding network in the solid state, forming complex layers parallel to the crystallographic bc plane. The inter­layer distance is 11.336 (12) Å. The mol­ecules pack in an alternating up-down fashion in the plane of the layers so that the SeO₃ and Li(H₂O)₃ groups are adjacent, creating a double net of hydrogen bonding between the two groups. Each of the six H atoms of the water mol­ecules forms hydrogen bonds, with five to O atoms of the phenyl­selenonate and one to the O atom of a neighboring water mol­ecule. The Li cation has a tetra­hedral geometry formed by one O atom of the phenyl­selenonate anion and three water mol­ecules. The Li-O distances are in the range 1.896 (8)-1.921 (9) Å to the water mol­ecules and 1.988 (8) Å to the phenyl­selenonate.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.008 Å
• R factor = 0.042
• wR factor = 0.088
• Data-to-parameter ratio = 14.2

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large .............       0.89
PLAT331_ALERT_2_C Small Average Phenyl C-C Dist.   C1     -C6            1.37 Ang.
PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          8

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   3 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
   2 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: COSMO/APEX2/BIS (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: WinGX (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

triaqua(phenylselenonato)lithium(I)

Crystal data

[Li(C6H5O3Se)(H2O)3]	F(000) = 528
Mr = 265.05	Dx = 1.657 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 872 reflections
a = 11.3410 (11) Å	θ = 3.2–19.0°
b = 7.6180 (8) Å	µ = 3.53 mm^−1
c = 12.3021 (13) Å	T = 296 K
β = 91.720 (6)°	Plate, colourless
V = 1062.37 (19) Å^3	0.10 × 0.10 × 0.02 mm
Z = 4

Data collection

Bruker Model? CCD area-detector diffractometer	1364 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.082
φ and ω scans	θmax = 26.4°, θmin = 3.2°
Absorption correction: multi-scan (SADABS; Bruker, 2004); tramsmission factors rescaled by 0.93	h = −14→14
Tmin = 0.63, Tmax = 0.93	k = −9→9
8507 measured reflections	l = −15→14
2147 independent reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.088	H atoms treated by a mixture of independent and constrained refinement
S = 0.99	w = 1/[σ^2(Fo^2) + (0.0351P)^2] where P = (Fo^2 + 2Fc^2)/3
2147 reflections	(Δ/σ)max = 0.001
151 parameters	Δρmax = 0.66 e Å^−3
9 restraints	Δρmin = −0.58 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
Li1	0.5530 (6)	0.3183 (11)	0.3927 (6)	0.040 (2)
Se1	0.28611 (4)	0.19615 (6)	0.43954 (4)	0.03132 (16)
O1	0.3781 (2)	0.3371 (4)	0.3904 (3)	0.0418 (9)
O2	0.3005 (3)	0.1756 (4)	0.5705 (2)	0.0457 (9)
O3	0.2967 (2)	0.0080 (4)	0.3781 (2)	0.0405 (9)
C1	0.1319 (4)	0.2792 (6)	0.4075 (4)	0.0359 (11)
C2	0.0440 (4)	0.2343 (7)	0.4751 (5)	0.0558 (16)
H2	0.0615	0.1732	0.5391	0.067*
C3	−0.0711 (5)	0.2798 (9)	0.4484 (6)	0.080 (2)
H3	−0.1322	0.2475	0.4931	0.096*
C4	−0.0935 (6)	0.3723 (10)	0.3560 (7)	0.086 (2)
H4	−0.1707	0.4051	0.3383	0.103*
C6	0.1090 (4)	0.3711 (7)	0.3137 (4)	0.0529 (15)
H6	0.1696	0.4009	0.2679	0.064*
C5	−0.0060 (5)	0.4185 (9)	0.2885 (6)	0.079 (2)
H5	−0.0237	0.4819	0.2255	0.095*
O1W	0.5941 (3)	0.5316 (5)	0.3196 (3)	0.0414 (9)
O2W	0.6273 (4)	0.3093 (7)	0.5327 (3)	0.0570 (10)
O3W	0.6102 (3)	0.1208 (5)	0.3143 (3)	0.0536 (10)
H11	0.614 (4)	0.626 (5)	0.349 (4)	0.06 (2)*
H12	0.634 (5)	0.520 (7)	0.262 (3)	0.10 (2)*
H21	0.639 (4)	0.394 (4)	0.569 (4)	0.052 (19)*
H22	0.647 (4)	0.214 (4)	0.560 (4)	0.057 (18)*
H31	0.556 (4)	0.082 (8)	0.272 (4)	0.12 (3)*
H32	0.633 (4)	0.040 (6)	0.355 (4)	0.06 (2)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Li1	0.040 (4)	0.044 (6)	0.035 (5)	0.001 (4)	0.006 (3)	−0.001 (4)
Se1	0.0356 (2)	0.0276 (3)	0.0307 (3)	0.0004 (3)	0.00149 (16)	0.0001 (3)
O1	0.0341 (16)	0.033 (3)	0.058 (2)	−0.0032 (14)	0.0066 (15)	0.0048 (16)
O2	0.062 (2)	0.048 (3)	0.0272 (19)	0.0026 (18)	−0.0028 (15)	0.0001 (15)
O3	0.058 (2)	0.028 (2)	0.035 (2)	0.0067 (17)	0.0043 (16)	−0.0020 (14)
C1	0.037 (2)	0.033 (3)	0.038 (3)	0.002 (2)	0.001 (2)	−0.005 (2)
C2	0.051 (3)	0.052 (4)	0.065 (4)	−0.001 (3)	0.013 (3)	0.008 (3)
C3	0.047 (3)	0.080 (6)	0.113 (6)	0.001 (4)	0.018 (4)	−0.003 (5)
C4	0.046 (4)	0.097 (7)	0.115 (7)	0.027 (4)	−0.003 (4)	−0.002 (5)
C6	0.052 (3)	0.054 (4)	0.052 (4)	0.016 (3)	0.007 (3)	0.013 (3)
C5	0.066 (4)	0.085 (6)	0.084 (5)	0.026 (4)	−0.012 (4)	0.019 (4)
O1W	0.055 (2)	0.035 (3)	0.034 (2)	−0.0052 (19)	0.0059 (18)	0.0012 (17)
O2W	0.086 (3)	0.040 (3)	0.044 (2)	0.014 (3)	−0.0128 (19)	0.000 (2)
O3W	0.060 (2)	0.048 (3)	0.053 (3)	0.010 (2)	−0.013 (2)	−0.008 (2)

Geometric parameters (Å, º)

Li1—O1W	1.921 (9)	C3—H3	0.9300
Li1—O2W	1.896 (8)	C4—C5	1.359 (8)
Li1—O3W	1.911 (9)	C4—H4	0.9300
Li1—O1	1.988 (8)	C6—C5	1.380 (7)
Se1—O1	1.626 (3)	C6—H6	0.9300
Se1—O2	1.622 (3)	C5—H5	0.9300
Se1—O3	1.627 (3)	O1W—H11	0.83 (3)
Se1—C1	1.890 (4)	O1W—H12	0.86 (3)
C1—C2	1.362 (6)	O2W—H21	0.80 (2)
C1—C6	1.367 (6)	O2W—H22	0.83 (2)
C2—C3	1.381 (7)	O3W—H31	0.85 (3)
C2—H2	0.9300	O3W—H32	0.83 (3)
C3—C4	1.356 (9)
O2W—Li1—O1W	110.4 (4)	C4—C3—H3	120.6
O3W—Li1—O1W	109.8 (4)	C2—C3—H3	120.6
O2W—Li1—O3W	106.3 (4)	C3—C4—C5	121.7 (6)
O2W—Li1—O1	115.6 (4)	C3—C4—H4	119.2
O3W—Li1—O1	113.8 (4)	C5—C4—H4	119.2
O1W—Li1—O1	100.8 (4)	C1—C6—C5	118.6 (5)
O2—Se1—O1	112.75 (16)	C1—C6—H6	120.7
O2—Se1—O3	111.74 (16)	C5—C6—H6	120.7
O1—Se1—O3	110.58 (16)	C4—C5—C6	119.8 (6)
O2—Se1—C1	107.72 (18)	C4—C5—H5	120.1
O1—Se1—C1	107.51 (18)	C6—C5—H5	120.1
O3—Se1—C1	106.19 (18)	Li1—O1W—H11	127 (4)
Se1—O1—Li1	126.7 (3)	Li1—O1W—H12	116 (4)
C2—C1—C6	121.4 (5)	H11—O1W—H12	107 (4)
C2—C1—Se1	118.5 (4)	Li1—O2W—H21	123 (3)
C6—C1—Se1	119.9 (4)	Li1—O2W—H22	121 (3)
C1—C2—C3	119.7 (6)	H21—O2W—H22	116 (4)
C1—C2—H2	120.2	Li1—O3W—H31	109 (4)
C3—C2—H2	120.2	Li1—O3W—H32	113 (4)
C4—C3—C2	118.8 (6)	H31—O3W—H32	108 (4)
O2—Se1—O1—Li1	64.1 (4)	O1—Se1—C1—C6	32.9 (5)
O3—Se1—O1—Li1	−61.8 (4)	O3—Se1—C1—C6	−85.5 (5)
C1—Se1—O1—Li1	−177.3 (4)	C6—C1—C2—C3	0.9 (9)
O2W—Li1—O1—Se1	−61.3 (6)	Se1—C1—C2—C3	−174.2 (5)
O3W—Li1—O1—Se1	62.2 (5)	C1—C2—C3—C4	−1.5 (10)
O1W—Li1—O1—Se1	179.7 (3)	C2—C3—C4—C5	1.1 (12)
O2—Se1—C1—C2	−30.2 (5)	C2—C1—C6—C5	0.2 (9)
O1—Se1—C1—C2	−151.9 (4)	Se1—C1—C6—C5	175.2 (5)
O3—Se1—C1—C2	89.7 (4)	C3—C4—C5—C6	−0.1 (12)
O2—Se1—C1—C6	154.7 (4)	C1—C6—C5—C4	−0.6 (10)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H11···O2^i	0.83 (3)	2.04 (3)	2.852 (5)	166 (5)
O1W—H12···O3^ii	0.86 (3)	1.91 (3)	2.767 (5)	171 (6)
O2W—H21···O1^i	0.80 (2)	2.12 (3)	2.856 (6)	154 (5)
O2W—H22···O3^iii	0.83 (2)	1.96 (3)	2.781 (6)	176 (5)
O3W—H31···O1W^iv	0.85 (3)	2.05 (3)	2.883 (5)	168 (6)
O3W—H32···O2^iii	0.83 (3)	2.02 (3)	2.836 (5)	170 (6)

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