catena-Poly[[[diaqua­barium(II)]-bis­[μ-2-(4-carboxy­phen­oxy)propionato-κ³O,O′:O′] dihydrate]

In the crystal structure of the polymeric title compound, {[Ba(C₁₀H₉O₅)₂(H₂O)₂]·2H₂O}_n, the Ba^II atom is O,O′-chelated by the carboxyl­ate end of two 2-(4-carboxy­phen­oxy)propionate monoanions, and is coordinated by two water mol­ecules. It also inter­acts with the carboxyl­ate O atom of two adjacent monoanions; these bonds give rise to a chain structure along the c axis. Meanwhile, the carboxyl –CO₂H end of the anion interacts with an acceptor site [O...O = 2.608 (2) Å]; this interaction and hydrogen bonding involving the coordinated and lattice water molecules give rise to a three-dimensional network. The eight coordinating O atoms comprise a square-anti­prism around the metal atom, which lies on a special position of site symmetry 2.

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](C-C) = 0.003 Å
• Disorder in solvent or counterion
• R factor = 0.022
• wR factor = 0.058
• Data-to-parameter ratio = 16.0

checkCIF/PLATON results

No syntax errors found



Alert level C
ABSTM02_ALERT_3_C  The ratio of expected to reported Tmax/Tmin(RR') is < 0.90
            Tmin and Tmax reported:      0.471     0.629
            Tmin(prime) and Tmax expected:      0.515     0.600
            RR(prime) =      0.873
            Please check that your absorption correction is appropriate.
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large .............       0.85
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.95
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       3.35
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        Ba1
PLAT302_ALERT_4_C Anion/Solvent Disorder .........................      50.00 Perc.
PLAT313_ALERT_2_C Oxygen with three covalent bonds (rare) ........       O2W'
PLAT313_ALERT_2_C Oxygen with three covalent bonds (rare) ........        O2W
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          1

Alert level G
PLAT793_ALERT_1_G Check the Absolute Configuration of C2     = ...          R
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......         12

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
  10 ALERT level C = Check and explain
   2 ALERT level G = General alerts; check

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

---

S1. Comment

This report continues a previous study on the main-group metal derivative of 2-[4-carboxylatophenoxy]propionic acid (Kong et al., 2007). In the present barium compound (Fig. 1), the metal shows irregular square-antiprismatic coordination (Fig. 2).

Related literature

For the strontium derivative of 2-(4-carboxyphenoxy)propionic acid, see: Kong et al. (2007).

S2. Experimental

To a suspension of barium carbonate (2 mmol) in water was added 2-(4-carboxylatophenoxy)propionic acid (1 mmol). The mixture was heated to dissolve most of the carbonate; the unchanged reagent was removed by filtration. Colourless crystals separated out after a few days. C&H elemental analysis. Calculated for C₂₀H₂₂O₁₄Ba: C 38.51, H 3.56%; found: C 38.52, H 3.55%.

S3. Refinement

The lattice water molecule is disordered over two positions; as the occupancy refined to a nearly 50:50 ratio, the occupancy was fixed as 0.5 each. Carbon- and oxygen-bound H atoms were placed in calculated positions [C—H = 0.93–0.97 Å and U_iso(H) = 1.2–1.5U_eq(C); O–H = 0.82 Å and U_iso(H) = 1.5U_eq(O)], and were included in the refinement in the riding-model approximation. The final difference Fourier map had large peaks/holes in the vicinity of the barium atom.

Computing details

Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO (Rigaku, 1998); data reduction: CrystalStructure (Rigaku/MSC, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2007).

Figures

	Fig. 1. Part of the polymeric structure of the title compound, showing 50% probability displacement ellipsoids. H atoms are shown as small spheres of arbitrary radii. The disordered lattice water molecule is not shown. Symmetry codes; (i) 1 - x, y, 1/2 - z; (ii) 1 - x, 1 - y, 1 - z; (iii) x, 1 - y, z - 1/2.
	Fig. 2. Square-antiprimastic geometry of Ba.

catena-Poly[[[diaquabarium(II)]-bis[µ-2-(4-carboxyphenoxy)propionato-\k³O,O':O'] dihydrate]

Crystal data

[Ba(C10H9O5)2(H2O)2]·2H2O	F(000) = 1256
Mr = 627.75	Dx = 1.715 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 11193 reflections
a = 24.5348 (8) Å	θ = 3.0–27.5°
b = 13.2964 (4) Å	µ = 1.70 mm^−1
c = 7.5147 (2) Å	T = 295 K
β = 97.3494 (9)°	Prism, colourless
V = 2431.34 (13) Å^3	0.38 × 0.32 × 0.30 mm
Z = 4

Data collection

Rigaku R-AXIS RAPID diffractometer	2754 independent reflections
Radiation source: fine-focus sealed tube	2684 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.030
Detector resolution: 10.000 pixels mm^-1	θmax = 27.4°, θmin = 3.1°
ω scans	h = −31→31
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	k = −16→17
Tmin = 0.471, Tmax = 0.629	l = −8→9
11558 measured 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)] = 0.022	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.058	H-atom parameters constrained
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0386P)^2 + 1.6587P] where P = (Fo^2 + 2Fc^2)/3
2754 reflections	(Δ/σ)max = 0.001
172 parameters	Δρmax = 1.34 e Å^−3
12 restraints	Δρmin = −0.40 e Å^−3

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
Ba1	0.5000	0.602876 (9)	0.2500	0.02394 (7)
O1	0.44439 (6)	0.53508 (11)	0.5434 (2)	0.0362 (3)
O2	0.39379 (6)	0.62910 (11)	0.34507 (19)	0.0297 (3)
O3	0.31354 (5)	0.64630 (9)	0.56511 (18)	0.0280 (3)
O4	0.11457 (8)	0.38322 (13)	0.1840 (3)	0.0499 (5)
O5	0.17634 (7)	0.26668 (11)	0.2823 (2)	0.0447 (4)
H51	0.1561	0.2206	0.2426	0.067*
O1W	0.51164 (8)	0.77491 (13)	0.0446 (3)	0.0548 (4)
H11	0.5391	0.8060	0.0874	0.082*
H12	0.4844	0.8107	0.0450	0.082*
O2W	0.4618 (3)	0.9497 (5)	−0.1321 (11)	0.103 (2)	0.50
H21	0.4457	0.9907	−0.2014	0.155*	0.50
H22	0.4945	0.9641	−0.1136	0.155*	0.50
O2W'	0.4433 (3)	0.9510 (6)	0.0023 (12)	0.112 (2)	0.50
H23	0.4151	0.9849	−0.0095	0.168*	0.50
H24	0.4656	0.9757	0.0807	0.168*	0.50
C1	0.40400 (8)	0.59159 (13)	0.4991 (3)	0.0250 (4)
C2	0.36759 (8)	0.61791 (14)	0.6437 (3)	0.0267 (4)
H2	0.3653	0.5601	0.7233	0.032*
C3	0.39133 (10)	0.70747 (18)	0.7519 (3)	0.0434 (5)
H3A	0.3697	0.7207	0.8472	0.065*
H3B	0.3908	0.7653	0.6753	0.065*
H3C	0.4285	0.6931	0.8017	0.065*
C4	0.27903 (7)	0.57216 (14)	0.4905 (2)	0.0244 (3)
C5	0.22872 (9)	0.60562 (12)	0.4031 (3)	0.0305 (4)
H5	0.2212	0.6741	0.3946	0.037*
C6	0.19019 (8)	0.53692 (15)	0.3293 (3)	0.0317 (4)
H6	0.1566	0.5593	0.2713	0.038*
C7	0.20121 (8)	0.43396 (14)	0.3409 (2)	0.0282 (4)
C8	0.25192 (9)	0.40175 (13)	0.4258 (3)	0.0301 (4)
H8	0.2597	0.3333	0.4323	0.036*
C9	0.29105 (8)	0.46983 (14)	0.5007 (2)	0.0281 (4)
H9	0.3248	0.4475	0.5570	0.034*
C10	0.15978 (8)	0.36010 (15)	0.2615 (3)	0.0321 (4)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Ba1	0.02067 (9)	0.02101 (9)	0.02963 (10)	0.000	0.00124 (6)	0.000
O1	0.0281 (7)	0.0376 (8)	0.0434 (8)	0.0131 (6)	0.0060 (6)	0.0122 (6)
O2	0.0259 (7)	0.0305 (6)	0.0323 (7)	0.0063 (5)	0.0022 (5)	0.0042 (6)
O3	0.0206 (6)	0.0219 (6)	0.0408 (7)	0.0004 (5)	0.0012 (5)	−0.0063 (5)
O4	0.0330 (9)	0.0379 (8)	0.0736 (13)	−0.0037 (7)	−0.0131 (8)	−0.0042 (8)
O5	0.0411 (9)	0.0255 (7)	0.0619 (10)	−0.0062 (6)	−0.0150 (7)	−0.0053 (7)
O1W	0.0519 (11)	0.0370 (9)	0.0724 (12)	−0.0018 (7)	−0.0037 (9)	0.0129 (8)
O2W	0.079 (4)	0.069 (3)	0.155 (6)	0.015 (3)	−0.018 (4)	0.018 (4)
O2W'	0.087 (4)	0.094 (4)	0.151 (6)	0.030 (3)	0.003 (4)	0.034 (4)
C1	0.0208 (9)	0.0208 (8)	0.0326 (10)	0.0002 (6)	0.0010 (7)	−0.0004 (6)
C2	0.0223 (9)	0.0269 (8)	0.0304 (9)	−0.0004 (7)	0.0014 (7)	−0.0020 (7)
C3	0.0353 (11)	0.0449 (12)	0.0485 (12)	−0.0050 (9)	−0.0001 (9)	−0.0205 (10)
C4	0.0216 (8)	0.0234 (8)	0.0284 (8)	−0.0011 (7)	0.0039 (6)	−0.0033 (7)
C5	0.0266 (10)	0.0232 (9)	0.0407 (11)	0.0036 (6)	−0.0001 (8)	−0.0022 (7)
C6	0.0248 (9)	0.0296 (9)	0.0390 (10)	0.0025 (7)	−0.0024 (7)	−0.0031 (8)
C7	0.0274 (9)	0.0258 (9)	0.0307 (9)	−0.0035 (7)	0.0012 (7)	−0.0030 (7)
C8	0.0314 (11)	0.0223 (9)	0.0360 (11)	−0.0005 (6)	0.0018 (8)	0.0004 (6)
C9	0.0238 (8)	0.0253 (8)	0.0342 (9)	0.0016 (7)	−0.0003 (7)	−0.0011 (7)
C10	0.0296 (10)	0.0304 (10)	0.0354 (10)	−0.0049 (8)	0.0008 (7)	−0.0034 (8)

Geometric parameters (Å, º)

Ba1—O1	2.882 (1)	O2W'—H23	0.82
Ba1—O1^i	2.882 (1)	O2W'—H24	0.82
Ba1—O1^ii	2.664 (1)	C1—C2	1.533 (3)
Ba1—O1^iii	2.664 (1)	C2—C3	1.515 (3)
Ba1—O2	2.811 (1)	C2—H2	0.98
Ba1—O2^i	2.811 (1)	C3—H3A	0.96
Ba1—O1W	2.794 (2)	C3—H3B	0.96
Ba1—O1W^i	2.794 (2)	C3—H3C	0.96
O1—C1	1.254 (2)	C4—C5	1.395 (3)
O2—C1	1.256 (3)	C4—C9	1.392 (2)
O3—C4	1.371 (2)	C5—C6	1.379 (3)
O3—C2	1.432 (2)	C5—H5	0.93
O4—C10	1.224 (3)	C6—C7	1.396 (3)
O5—C10	1.310 (3)	C6—H6	0.93
O5—H51	0.82	C7—C8	1.391 (3)
O1W—H11	0.82	C7—C10	1.483 (3)
O1W—H12	0.82	C8—C9	1.386 (3)
O2W—H21	0.82	C8—H8	0.93
O2W—H22	0.82	C9—H9	0.93
O1^iii—Ba1—O1^ii	92.96 (7)	H23—O2W'—H24	109.5
O1^iii—Ba1—O1W^i	143.59 (5)	O1—C1—O2	122.68 (18)
O1^ii—Ba1—O1W^i	108.82 (5)	O1—C1—C2	117.47 (18)
O1^iii—Ba1—O1W	108.82 (5)	O2—C1—C2	119.80 (17)
O1^ii—Ba1—O1W	143.59 (5)	O3—C2—C3	106.64 (16)
O1W^i—Ba1—O1W	70.11 (9)	O3—C2—C1	111.15 (16)
O1^iii—Ba1—O2^i	111.08 (4)	C3—C2—C1	109.92 (17)
O1^ii—Ba1—O2^i	79.11 (4)	O3—C2—H2	109.7
O1W^i—Ba1—O2^i	101.68 (5)	C3—C2—H2	109.7
O1W—Ba1—O2^i	66.08 (5)	C1—C2—H2	109.7
O1^iii—Ba1—O2	79.11 (4)	C2—C3—H3A	109.5
O1^ii—Ba1—O2	111.08 (4)	C2—C3—H3B	109.5
O1W^i—Ba1—O2	66.08 (5)	H3A—C3—H3B	109.5
O1W—Ba1—O2	101.68 (5)	C2—C3—H3C	109.5
O2^i—Ba1—O2	165.75 (6)	H3A—C3—H3C	109.5
O1^iii—Ba1—O1^i	66.17 (5)	H3B—C3—H3C	109.5
O1^ii—Ba1—O1^i	88.46 (3)	O3—C4—C5	115.21 (16)
O1W^i—Ba1—O1^i	140.39 (5)	O3—C4—C9	124.37 (17)
O1W—Ba1—O1^i	75.03 (5)	C5—C4—C9	120.40 (16)
O2^i—Ba1—O1^i	45.51 (4)	C6—C5—C4	119.87 (16)
O2—Ba1—O1^i	141.12 (4)	C6—C5—H5	120.1
O1^iii—Ba1—O1	88.46 (3)	C4—C5—H5	120.1
O1^ii—Ba1—O1	66.17 (5)	C5—C6—C7	120.46 (18)
O1W^i—Ba1—O1	75.03 (5)	C5—C6—H6	119.8
O1W—Ba1—O1	140.39 (5)	C7—C6—H6	119.8
O2^i—Ba1—O1	141.12 (4)	C8—C7—C6	119.04 (17)
O2—Ba1—O1	45.51 (4)	C8—C7—C10	120.50 (17)
O1^i—Ba1—O1	143.54 (6)	C6—C7—C10	120.45 (18)
C1—O1—Ba1^ii	153.58 (13)	C9—C8—C7	121.17 (16)
C1—O1—Ba1	92.59 (12)	C9—C8—H8	119.4
Ba1^ii—O1—Ba1	113.83 (5)	C7—C8—H8	119.4
C1—O2—Ba1	95.91 (11)	C8—C9—C4	119.03 (17)
C4—O3—C2	118.03 (14)	C8—C9—H9	120.5
C10—O5—H51	120.0	C4—C9—H9	120.5
Ba1—O1W—H11	109.5	O4—C10—O5	122.92 (19)
Ba1—O1W—H12	109.5	O4—C10—C7	123.91 (19)
H11—O1W—H12	109.5	O5—C10—C7	113.18 (17)
H21—O2W—H22	109.5
O1^iii—Ba1—O1—C1	−86.03 (10)	Ba1—O2—C1—O1	−19.5 (2)
O1^ii—Ba1—O1—C1	−179.94 (16)	Ba1—O2—C1—C2	158.09 (14)
O1W^i—Ba1—O1—C1	61.17 (12)	C4—O3—C2—C3	−167.01 (16)
O1W—Ba1—O1—C1	32.26 (15)	C4—O3—C2—C1	73.20 (19)
O2^i—Ba1—O1—C1	151.29 (11)	O1—C1—C2—O3	−156.65 (17)
O2—Ba1—O1—C1	−9.82 (11)	O2—C1—C2—O3	25.7 (2)
O1^i—Ba1—O1—C1	−130.27 (12)	O1—C1—C2—C3	85.5 (2)
O1^iii—Ba1—O1—Ba1^ii	93.91 (9)	O2—C1—C2—C3	−92.1 (2)
O1^ii—Ba1—O1—Ba1^ii	0.0	C2—O3—C4—C5	−174.86 (17)
O1W^i—Ba1—O1—Ba1^ii	−118.89 (7)	C2—O3—C4—C9	6.3 (3)
O1W—Ba1—O1—Ba1^ii	−147.80 (7)	O3—C4—C5—C6	−177.60 (18)
O2^i—Ba1—O1—Ba1^ii	−28.77 (10)	C9—C4—C5—C6	1.3 (3)
O2—Ba1—O1—Ba1^ii	170.12 (9)	C4—C5—C6—C7	−0.2 (3)
O1^i—Ba1—O1—Ba1^ii	49.68 (5)	C5—C6—C7—C8	−1.0 (3)
O1^iii—Ba1—O2—C1	108.52 (12)	C5—C6—C7—C10	−180.0 (2)
O1^ii—Ba1—O2—C1	19.54 (12)	C6—C7—C8—C9	1.0 (3)
O1W^i—Ba1—O2—C1	−82.42 (12)	C10—C7—C8—C9	−179.97 (19)
O1W—Ba1—O2—C1	−144.28 (11)	C7—C8—C9—C4	0.1 (3)
O2^i—Ba1—O2—C1	−114.53 (11)	O3—C4—C9—C8	177.54 (18)
O1^i—Ba1—O2—C1	135.15 (11)	C5—C4—C9—C8	−1.2 (3)
O1—Ba1—O2—C1	9.85 (10)	C8—C7—C10—O4	−179.5 (2)
Ba1^ii—O1—C1—O2	−161.0 (2)	C6—C7—C10—O4	−0.5 (3)
Ba1—O1—C1—O2	18.88 (19)	C8—C7—C10—O5	0.5 (3)
Ba1^ii—O1—C1—C2	21.4 (4)	C6—C7—C10—O5	179.5 (2)
Ba1—O1—C1—C2	−158.73 (14)

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O5—H51···O2^iv	0.82	1.79	2.608 (2)	174
O1W—H11···O4^v	0.82	2.16	2.979 (3)	176
O1W—H12···O2W′	0.82	2.13	2.875 (7)	152
O2W—H21···O4^vi	0.82	2.25	2.900 (6)	137
O2W—H22···O2W^vii	0.82	2.32	2.881 (14)	126
O2W—H22···O2W^viii	0.82	2.32	2.742 (17)	113
O2W—H22···O2W′^vii	0.82	1.99	2.746 (9)	152
O2W′—H23···O4^vi	0.82	2.25	2.885 (7)	134
O2W′—H24···O2W^vii	0.82	2.03	2.746 (9)	145

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