Di­aqua­di(L-lactato)­nickel(II)

The two L-lactate groups in di­aqua­di(L-lactato)­nickel(II), [Ni(C₃H₅O₃)₂(H₂O)₂], chelate to the Ni atom through their carboxyl and hydroxy O atoms; the water mol­ecules occupy cis positions in the coordination octahedron of the metal atom. The water mol­ecules and hydroxy groups are engaged in hydrogen bonds, to furnish a tightly held three-dimensional network structure.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.010 Å
• R factor = 0.047
• wR factor = 0.113
• Data-to-parameter ratio = 8.9

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


 Alert Level B:



PLAT_731  Alert B Bond    Calc     0.85(5), Rep   0.850(10) ....       5.00 s.u-Ratio
                     O3   -H3O     1.555   1.555

PLAT_731  Alert B Bond    Calc     0.85(5), Rep   0.850(10) ....       5.00 s.u-Ratio
                     O6   -H6O     1.555   1.555

PLAT_735  Alert B D-H     Calc     0.85(5), Rep   0.850(10) ....       5.00 s.u-Ratio
                     O3   -H3O     1.555   1.555

PLAT_735  Alert B D-H     Calc     0.85(5), Rep   0.850(10) ....       5.00 s.u-Ratio
                     O6   -H6O     1.555   1.555

PLAT_736  Alert B H...A   Calc     1.81(6), Rep   1.810(10) ....       6.00 s.u-Ratio
                     H3O  -O4      1.555   3.456


 Alert Level C:



PLAT_731  Alert C Bond    Calc     0.85(4), Rep   0.850(10) ....       4.00 s.u-Ratio
                     O1W  -H1W2    1.555   1.555

PLAT_731  Alert C Bond    Calc     0.85(4), Rep   0.850(10) ....       4.00 s.u-Ratio
                     O2W  -H2W1    1.555   1.555

PLAT_731  Alert C Bond    Calc     0.85(4), Rep   0.850(10) ....       4.00 s.u-Ratio
                     O2W  -H2W2    1.555   1.555

PLAT_732  Alert C Angle   Calc      108(6), Rep      110(2) ....       3.00 s.u-Ratio
                     H1W1 -O1W  -H1W2    1.555   1.555   1.555

PLAT_732  Alert C Angle   Calc      110(6), Rep      110(2) ....       3.00 s.u-Ratio
                     H2W1 -O2W  -H2W2    1.555   1.555   1.555

PLAT_735  Alert C D-H     Calc     0.85(4), Rep   0.850(10) ....       4.00 s.u-Ratio
                     O1W  -H1W1    1.555   1.555

PLAT_735  Alert C D-H     Calc     0.85(4), Rep   0.850(10) ....       4.00 s.u-Ratio
                     O1W  -H1W2    1.555   1.555

PLAT_735  Alert C D-H     Calc     0.85(4), Rep   0.850(10) ....       4.00 s.u-Ratio
                     O2W  -H2W2    1.555   1.555

PLAT_735  Alert C D-H     Calc     0.85(4), Rep   0.850(10) ....       4.00 s.u-Ratio
                     O2W  -H2W1    1.555   1.555

PLAT_736  Alert C H...A   Calc     1.92(5), Rep     1.92(2) ....       2.50 s.u-Ratio
                     H2W2 -O2      1.555   1.455

PLAT_736  Alert C H...A   Calc     1.85(5), Rep     1.85(2) ....       2.50 s.u-Ratio
                     H2W1 -O4      1.555   2.555

General Notes



ABSTM_02  When printed, the submitted absorption T values will be replaced
          by the scaled T values. Since the ratio of scaled T's is
          identical to the ratio of reported T values, the scaling does
          not imply a change to the absorption corrections used in the
          study.
          Ratio of Tmax expected/reported      1.074
          Tmax scaled      0.750 Tmin scaled      0.656

REFLT_03
         From the CIF: _diffrn_reflns_theta_max           27.50
         From the CIF: _reflns_number_total               1375
         Count of symmetry unique reflns         1375
         Completeness (_total/calc)            100.00%
         TEST3: Check Friedels for noncentro structure
         Estimate of Friedel pairs measured         0
         Fraction of Friedel pairs measured     0.000
         Are heavy atom types Z>Si present          yes
          WARNING: Large fraction of Friedel related reflns may
                   be needed to determine absolute structure


 0 Alert Level A = Potentially serious problem

 5 Alert Level B = Potential problem

 11 Alert Level C = Please check

---

Computing details

Data collection: CAD-4 VAX/PC (Enraf-Nonius, 1988); cell refinement: CAD-4 VAX/PC; data reduction: NRCVAX (Gabe et al., 1989); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.

Bis(L-lactato)diaquanickel(II)

Crystal data

[Ni(C3H5O3)2(H2O)2]	Dx = 1.773 Mg m^−3
Mr = 272.88	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121	Cell parameters from 25 reflections
a = 6.033 (1) Å	θ = 12.0–15.0°
b = 11.805 (1) Å	µ = 1.92 mm^−1
c = 14.354 (1) Å	T = 298 K
V = 1022.3 (2) Å^3	Block, green
Z = 4	0.30 × 0.19 × 0.15 mm
F(000) = 568

Data collection

Enraf-Nonius CAD-4 diffractometer	1138 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.000
Graphite monochromator	θmax = 27.5°, θmin = 2.2°
ω scans	h = 0→7
Absorption correction: empirical (using intensity measurements) via ψ scan (North et al., 1968)	k = 0→15
Tmin = 0.611, Tmax = 0.698	l = 0→18
1375 measured reflections	3 standard reflections every 60 min
1375 independent reflections	intensity decay: none

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.047	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.113	w = 1/[σ^2(Fo^2) + (0.0602P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.01	(Δ/σ)max = 0.001
1375 reflections	Δρmax = 0.78 e Å^−3
154 parameters	Δρmin = −0.57 e Å^−3
8 restraints	Absolute structure: Flack & Schwarzenbach (1988); no Friedel pairs, still the absolute configuration is in agreement with known L-lactate.
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.00 (4)

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

	x	y	z	Uiso*/Ueq
Ni1	0.2107 (1)	0.14551 (7)	0.64264 (5)	0.0184 (2)
O1	0.5193 (7)	0.1637 (4)	0.7046 (3)	0.025 (1)
O2	0.7150 (9)	0.2833 (4)	0.7907 (3)	0.032 (1)
O3	0.2359 (8)	0.3156 (4)	0.6510 (3)	0.028 (1)
O4	0.417 (1)	0.0376 (4)	0.3896 (3)	0.039 (1)
O5	0.3460 (8)	0.1432 (4)	0.5135 (3)	0.025 (1)
O6	0.224 (1)	−0.0247 (3)	0.6161 (3)	0.025 (1)
O1w	−0.0997 (8)	0.1530 (5)	0.5804 (3)	0.027 (1)
O2w	0.0622 (8)	0.1366 (5)	0.7694 (3)	0.029 (1)
C1	0.549 (1)	0.2612 (6)	0.7396 (5)	0.024 (1)
C2	0.387 (1)	0.3555 (6)	0.7204 (5)	0.027 (1)
C3	0.268 (1)	0.3949 (6)	0.8085 (5)	0.035 (2)
C4	0.348 (1)	0.0497 (5)	0.4714 (4)	0.022 (1)
C5	0.265 (1)	−0.0550 (5)	0.5215 (4)	0.026 (2)
C6	0.055 (2)	−0.1029 (8)	0.4746 (6)	0.051 (2)
H3o	0.129 (8)	0.360 (5)	0.639 (5)	0.033*
H6o	0.20 (1)	−0.073 (4)	0.659 (3)	0.030*
H1w1	−0.221 (6)	0.140 (5)	0.608 (4)	0.033*
H1w2	−0.11 (1)	0.217 (3)	0.553 (4)	0.033*
H2w1	0.06 (1)	0.077 (3)	0.802 (4)	0.035*
H2w2	−0.062 (6)	0.170 (5)	0.772 (5)	0.035*
H2	0.4693	0.4199	0.6945	0.032*
H3a	0.1672	0.4550	0.7931	0.052*
H3b	0.3750	0.4219	0.8528	0.052*
H3c	0.1872	0.3327	0.8349	0.052*
H5	0.3808	−0.1130	0.5199	0.032*
H6a	0.0058	−0.1690	0.5077	0.076*
H6b	0.0874	−0.1228	0.4112	0.076*
H6c	−0.0604	−0.0466	0.4756	0.076*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Ni1	0.0198 (4)	0.0180 (3)	0.0175 (3)	0.0008 (4)	0.0011 (4)	0.0004 (4)
O1	0.022 (2)	0.021 (2)	0.032 (2)	0.002 (2)	0.002 (2)	−0.010 (2)
O2	0.027 (2)	0.028 (2)	0.041 (3)	0.001 (2)	−0.007 (3)	−0.010 (2)
O3	0.033 (3)	0.023 (2)	0.027 (2)	0.007 (2)	−0.004 (3)	−0.004 (2)
O4	0.060 (4)	0.033 (3)	0.024 (2)	−0.015 (3)	0.018 (3)	−0.009 (2)
O5	0.032 (3)	0.020 (2)	0.024 (2)	0.000 (2)	0.008 (2)	−0.002 (2)
O6	0.039 (3)	0.020 (2)	0.017 (2)	0.002 (3)	0.006 (2)	0.003 (2)
O1w	0.027 (3)	0.030 (3)	0.024 (2)	0.004 (3)	−0.002 (2)	0.008 (2)
O2w	0.034 (3)	0.028 (3)	0.026 (2)	0.006 (3)	0.005 (2)	0.012 (2)
C1	0.019 (3)	0.024 (3)	0.030 (3)	0.004 (3)	0.003 (3)	−0.004 (3)
C2	0.027 (3)	0.019 (3)	0.034 (3)	−0.001 (3)	0.000 (3)	−0.001 (3)
C3	0.024 (4)	0.035 (4)	0.045 (4)	0.006 (3)	−0.001 (3)	−0.019 (3)
C4	0.023 (4)	0.020 (3)	0.023 (3)	−0.001 (3)	−0.001 (3)	−0.004 (3)
C5	0.037 (4)	0.020 (3)	0.022 (3)	0.005 (3)	0.003 (3)	0.001 (2)
C6	0.062 (6)	0.054 (5)	0.037 (4)	−0.036 (5)	0.001 (5)	−0.003 (4)

Geometric parameters (Å, º)

Ni1—O1	2.075 (5)	C5—C6	1.54 (1)
Ni1—O3	2.017 (4)	O3—H3o	0.85 (1)
Ni1—O5	2.025 (4)	O6—H6o	0.85 (1)
Ni1—O6	2.046 (4)	O1w—H1w1	0.85 (1)
Ni1—O1w	2.077 (5)	O1w—H1w2	0.85 (1)
Ni1—O2w	2.031 (4)	O2w—H2w1	0.85 (1)
O1—C1	1.269 (8)	O2w—H2w2	0.85 (1)
O2—C1	1.267 (8)	C2—H2	0.9800
O3—C2	1.431 (8)	C3—H3a	0.9600
O4—C4	1.254 (8)	C3—H3b	0.9600
O5—C4	1.257 (7)	C3—H3c	0.9600
O6—C5	1.427 (7)	C5—H5	0.9800
C1—C2	1.506 (9)	C6—H6a	0.9600
C2—C3	1.527 (9)	C6—H6b	0.9600
C4—C5	1.516 (8)	C6—H6c	0.9600
O1—Ni1—O3	78.7 (2)	C4—C5—C6	111.4 (6)
O1—Ni1—O5	91.8 (2)	C2—O3—H3o	115 (5)
O1—Ni1—O6	98.5 (2)	Ni1—O3—H3o	123 (5)
O1—Ni1—O1w	171.6 (2)	C5—O6—H6o	123 (5)
O1—Ni1—O2w	91.0 (2)	Ni1—O6—H6o	121 (5)
O3—Ni1—O5	92.2 (2)	Ni1—O1w—H1w1	125 (5)
O3—Ni1—O6	170.3 (2)	Ni1—O1w—H1w2	106 (5)
O3—Ni1—O1w	92.9 (2)	H1w1—O1w—H1w2	110 (2)
O3—Ni1—O2w	91.8 (2)	Ni1—O2w—H2w1	123 (4)
O5—Ni1—O6	78.5 (2)	Ni1—O2w—H2w2	114 (5)
O5—Ni1—O1w	88.3 (2)	H2w1—O2w—H2w2	110 (2)
O5—Ni1—O2w	175.5 (2)	O3—C2—H2	108.3
O6—Ni1—O1w	89.7 (2)	C1—C2—H2	108.3
O6—Ni1—O2w	97.6 (2)	C3—C2—H2	108.3
O1w—Ni1—O2w	89.4 (2)	C2—C3—H3a	109.5
C1—O1—Ni1	113.0 (4)	C2—C3—H3b	109.5
C2—O3—Ni1	114.7 (4)	H3a—C3—H3b	109.5
C4—O5—Ni1	117.1 (4)	C2—C3—H3c	109.5
C5—O6—Ni1	115.5 (3)	H3a—C3—H3c	109.5
O1—C1—O2	121.9 (6)	H3b—C3—H3c	109.5
O1—C1—C2	120.3 (6)	O6—C5—H5	108.8
O2—C1—C2	117.8 (6)	C4—C5—H5	108.8
O3—C2—C1	107.4 (6)	C6—C5—H5	108.8
O3—C2—C3	112.1 (6)	C5—C6—H6a	109.5
C1—C2—C3	112.3 (6)	C5—C6—H6b	109.5
O4—C4—O5	123.7 (6)	H6a—C6—H6b	109.5
O4—C4—C5	117.4 (5)	C5—C6—H6c	109.5
O5—C4—C5	119.0 (5)	H6a—C6—H6c	109.5
O6—C5—C4	107.7 (5)	H6b—C6—H6c	109.5
O6—C5—C6	111.4 (6)
O3—Ni1—O1—C1	17.6 (5)	Ni1—O1—C1—O2	170.7 (5)
O5—Ni1—O1—C1	109.4 (5)	Ni1—O1—C1—C2	−10.1 (8)
O2w—Ni1—O1—C1	−74.1 (5)	Ni1—O3—C2—C1	22.7 (6)
O6—Ni1—O1—C1	−171.9 (5)	Ni1—O3—C2—C3	−101.0 (6)
O5—Ni1—O3—C2	−113.9 (4)	O1—C1—C2—O3	−7.9 (9)
O2w—Ni1—O3—C2	68.2 (4)	O2—C1—C2—O3	171.4 (6)
O1—Ni1—O3—C2	−22.5 (4)	O1—C1—C2—C3	115.8 (7)
O1w—Ni1—O3—C2	157.7 (4)	O2—C1—C2—C3	−65.0 (8)
O3—Ni1—O5—C4	−173.4 (5)	Ni1—O5—C4—O4	176.3 (6)
O6—Ni1—O5—C4	9.6 (5)	Ni1—O5—C4—C5	−3.9 (8)
O1—Ni1—O5—C4	107.9 (5)	Ni1—O6—C5—C4	14.9 (7)
O1w—Ni1—O5—C4	−80.5 (5)	Ni1—O6—C5—C6	−107.5 (6)
O5—Ni1—O6—C5	−13.7 (5)	O4—C4—C5—O6	172.5 (7)
O2w—Ni1—O6—C5	164.0 (5)	O5—C4—C5—O6	−7.3 (9)
O1—Ni1—O6—C5	−103.9 (5)	O4—C4—C5—C6	−65.1 (9)
O1w—Ni1—O6—C5	74.6 (5)	O5—C4—C5—C6	115.1 (7)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1w—H1w1···O1^i	0.85 (1)	2.11 (3)	2.911 (6)	158 (7)
O1w—H1w2···O5^ii	0.85 (1)	1.93 (2)	2.778 (7)	174 (7)
O2w—H2w2···O2^i	0.85 (1)	1.92 (2)	2.735 (7)	162 (7)
O2w—H2w1···O4^iii	0.85 (1)	1.85 (2)	2.687 (7)	170 (7)
O3—H3o···O4^ii	0.85 (1)	1.81 (1)	2.657 (7)	176 (8)
O6—H6o···O2^iv	0.85 (1)	1.91 (4)	2.658 (6)	147 (7)

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