catena-Poly[[aqua-(benzoato-κO,O')(benzoic acid-κO)calcium]-μ(3)-benzoato-κO:O,O':O'].

In title compound, [Ca(C(7)H(5)O(2))(2)(C(7)H(6)O(2))(H(2)O)](n), the eightfold-coordinated Ca(II) ion is bonded to four carboxyl-ate O atoms from two benzoate ions, an O atom from benzoic acid and a water O atom. One of the carboxyl-ate groups bridges adjacent Ca(2+) ions, forming a polymeric ribbon structure parallel to [010]. In the crystal, the benzoate anions and water mol-ecule inter-act by way of inter- and intra-molecular O-H⋯O hydrogen bonds.

Related literature

For background to the crystal structures and physical stability of calcium benzoate hydrates, mesophases and related compounds, see: Cherkezova et al. (1987 ▶); Zhang et al. (1999 ▶); Yano et al. (2001 ▶); Senkovska & Thewalt (2005 ▶); Terakita & Byrn (2006 ▶).

Experimental

Crystal data

[Ca(C7H5O2)2(C7H6O2)(H2O)]

M = 422.43

Monoclinic,

a = 15.5535 (3) Å

b = 6.61183 (16) Å

c = 20.1828 (4) Å

β = 94.3750 (18)°

V = 2069.49 (8) Å3

Z = 4

Cu Kα radiation

μ = 2.96 mm−1

T = 293 K

0.55 × 0.45 × 0.40 mm

Data collection

Oxford Diffraction Xcalibur Ruby diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2007 ▶) T min = 0.782, T max = 1.000

7257 measured reflections

3847 independent reflections

2961 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.121

S = 1.07

3847 reflections

275 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.27 e Å−3

Δρmin = −0.26 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2007 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811013493/bv2180sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811013493/bv2180Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[Ca(C7H5O2)2(C7H6O2)(H2O)]	F(000) = 880
Mr = 422.43	Dx = 1.356 Mg m−3
Monoclinic, P21/n	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: -P 2yn	Cell parameters from 3133 reflections
a = 15.5535 (3) Å	θ = 3.5–70.6°
b = 6.61183 (16) Å	µ = 2.96 mm−1
c = 20.1828 (4) Å	T = 293 K
β = 94.3750 (18)°	Monoclinic, colourless
V = 2069.49 (8) Å3	0.55 × 0.45 × 0.40 mm
Z = 4

Oxford Diffraction Xcalibur Ruby diffractometer	3847 independent reflections
Radiation source: Enhance (Cu) X-ray Source	2961 reflections with I > 2σ(I)
graphite	Rint = 0.025
Detector resolution: 10.2576 pixels mm-1	θmax = 71.1°, θmin = 3.5°
q/2θ scans	h = −17→18
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2007)	k = −7→7
Tmin = 0.782, Tmax = 1.000	l = −22→24
7257 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.041	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.121	w = 1/[σ2(Fo2) + (0.0754P)2] where P = (Fo2 + 2Fc2)/3
S = 1.07	(Δ/σ)max < 0.001
3847 reflections	Δρmax = 0.27 e Å−3
275 parameters	Δρmin = −0.26 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0050 (4)

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.Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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.

	x	y	z	Uiso*/Ueq
Ca1	0.45197 (2)	0.25532 (5)	0.033347 (19)	0.03194 (16)
O1W	0.39727 (11)	0.2332 (3)	−0.08057 (9)	0.0443 (4)
O1	0.36276 (12)	0.5693 (3)	0.16770 (10)	0.0675 (6)
O2	0.33262 (10)	0.2999 (3)	0.10426 (9)	0.0508 (4)
O3	0.59059 (9)	0.0795 (2)	−0.02003 (7)	0.0394 (3)
O4	0.58487 (8)	0.4064 (2)	−0.00286 (7)	0.0368 (3)
O5	0.54914 (11)	0.1360 (2)	0.12874 (8)	0.0528 (4)
O6	0.51357 (9)	0.4557 (2)	0.13481 (7)	0.0430 (4)
C1	0.1629 (2)	0.2997 (6)	0.14566 (18)	0.0862 (11)
H1A	0.1815	0.1822	0.1258	0.103*
C2	0.0778 (2)	0.3155 (8)	0.1610 (2)	0.1124 (15)
H2A	0.0396	0.2089	0.1522	0.135*
C3	0.0512 (3)	0.4885 (8)	0.1889 (2)	0.1325 (19)
H3A	−0.0059	0.5006	0.1990	0.159*
C4	0.1074 (3)	0.6473 (9)	0.2026 (3)	0.1310 (18)
H4A	0.0881	0.7654	0.2216	0.157*
C5	0.1927 (2)	0.6303 (6)	0.18807 (18)	0.0944 (12)
H5A	0.2312	0.7358	0.1975	0.113*
C6	0.21971 (16)	0.4540 (4)	0.15927 (12)	0.0590 (7)
C7	0.31009 (15)	0.4324 (4)	0.14106 (12)	0.0499 (6)
C8	0.76481 (14)	0.4308 (4)	0.02152 (12)	0.0492 (6)
H8A	0.7323	0.5391	0.0351	0.059*
C9	0.85412 (16)	0.4419 (5)	0.02713 (15)	0.0660 (8)
H9A	0.8813	0.5579	0.0444	0.079*
C10	0.90217 (16)	0.2842 (5)	0.00760 (17)	0.0744 (9)
H10A	0.962	0.2931	0.0110	0.089*
C11	0.86257 (17)	0.1122 (5)	−0.01702 (18)	0.0801 (10)
H11A	0.8957	0.0043	−0.0301	0.096*
C12	0.77321 (15)	0.0979 (4)	−0.02254 (14)	0.0590 (7)
H12A	0.7466	−0.0201	−0.0386	0.071*
C13	0.72419 (13)	0.2590 (3)	−0.00417 (11)	0.0378 (5)
C14	0.62723 (12)	0.2463 (3)	−0.01012 (9)	0.0306 (4)
C15	0.59799 (16)	0.4938 (4)	0.26173 (12)	0.0542 (6)
H15A	0.5636	0.6006	0.2455	0.065*
C16	0.64396 (19)	0.5095 (5)	0.32353 (14)	0.0721 (8)
H16A	0.6395	0.626	0.3489	0.087*
C17	0.69539 (17)	0.3548 (6)	0.34678 (14)	0.0765 (9)
H17A	0.7262	0.3663	0.3879	0.092*
C18	0.70210 (18)	0.1819 (6)	0.31004 (15)	0.0743 (9)
H18A	0.7377	0.0771	0.3261	0.089*
C19	0.65589 (15)	0.1632 (5)	0.24906 (12)	0.0553 (6)
H19A	0.6600	0.0453	0.2244	0.066*
C20	0.60356 (13)	0.3198 (4)	0.22475 (10)	0.0401 (5)
C21	0.55280 (13)	0.3005 (3)	0.15892 (10)	0.0379 (5)
H1W1	0.4060 (18)	0.139 (5)	−0.1002 (14)	0.062 (10)*
H2W1	0.4184 (19)	0.325 (5)	−0.1072 (15)	0.074 (10)*
H1O	0.420 (2)	0.543 (5)	0.1603 (16)	0.090 (10)*

	U11	U22	U33	U12	U13	U23
Ca1	0.0308 (2)	0.0223 (2)	0.0429 (2)	−0.00138 (15)	0.00329 (15)	−0.00246 (16)
O1W	0.0509 (9)	0.0296 (9)	0.0512 (9)	0.0004 (7)	−0.0051 (7)	−0.0028 (8)
O1	0.0524 (11)	0.0671 (13)	0.0837 (13)	0.0043 (9)	0.0102 (9)	−0.0329 (11)
O2	0.0478 (9)	0.0470 (10)	0.0600 (10)	−0.0015 (7)	0.0187 (7)	−0.0103 (8)
O3	0.0376 (7)	0.0237 (8)	0.0574 (9)	−0.0041 (6)	0.0064 (6)	−0.0038 (6)
O4	0.0330 (7)	0.0254 (7)	0.0518 (8)	0.0025 (6)	0.0030 (6)	−0.0031 (6)
O5	0.0690 (10)	0.0360 (9)	0.0523 (9)	0.0049 (8)	−0.0028 (8)	−0.0066 (8)
O6	0.0437 (8)	0.0357 (9)	0.0490 (8)	0.0028 (6)	−0.0005 (6)	0.0012 (7)
C1	0.0648 (19)	0.103 (2)	0.096 (2)	−0.0124 (18)	0.0364 (17)	−0.032 (2)
C2	0.065 (2)	0.153 (4)	0.124 (3)	−0.024 (2)	0.044 (2)	−0.046 (3)
C3	0.062 (2)	0.193 (5)	0.148 (4)	0.011 (3)	0.043 (2)	−0.056 (4)
C4	0.079 (3)	0.162 (4)	0.157 (4)	0.029 (3)	0.039 (3)	−0.064 (4)
C5	0.074 (2)	0.105 (3)	0.107 (3)	0.015 (2)	0.0255 (18)	−0.039 (2)
C6	0.0508 (14)	0.0750 (19)	0.0526 (13)	0.0080 (13)	0.0136 (11)	−0.0091 (13)
C7	0.0498 (13)	0.0520 (15)	0.0491 (13)	0.0048 (11)	0.0109 (10)	−0.0039 (12)
C8	0.0369 (11)	0.0421 (14)	0.0681 (15)	−0.0041 (10)	0.0007 (10)	−0.0077 (12)
C9	0.0414 (13)	0.0679 (19)	0.0874 (19)	−0.0160 (13)	−0.0035 (12)	−0.0104 (16)
C10	0.0273 (11)	0.094 (2)	0.102 (2)	−0.0010 (14)	0.0051 (13)	−0.0049 (19)
C11	0.0390 (13)	0.083 (2)	0.119 (3)	0.0131 (15)	0.0089 (14)	−0.023 (2)
C12	0.0383 (12)	0.0518 (15)	0.0873 (19)	0.0051 (11)	0.0074 (11)	−0.0166 (14)
C13	0.0307 (10)	0.0364 (12)	0.0462 (11)	−0.0009 (8)	0.0028 (8)	0.0014 (9)
C14	0.0296 (9)	0.0256 (10)	0.0368 (10)	−0.0008 (8)	0.0045 (7)	0.0006 (8)
C15	0.0518 (13)	0.0597 (16)	0.0507 (13)	0.0025 (12)	0.0003 (10)	−0.0096 (12)
C16	0.0679 (17)	0.089 (2)	0.0579 (15)	−0.0055 (16)	−0.0038 (13)	−0.0217 (16)
C17	0.0522 (15)	0.126 (3)	0.0501 (15)	0.0002 (18)	−0.0076 (12)	0.0002 (18)
C18	0.0553 (16)	0.106 (2)	0.0605 (16)	0.0200 (17)	−0.0007 (13)	0.0175 (18)
C19	0.0498 (13)	0.0640 (17)	0.0524 (13)	0.0115 (12)	0.0053 (11)	0.0037 (13)
C20	0.0339 (10)	0.0482 (13)	0.0388 (11)	−0.0014 (9)	0.0059 (8)	0.0021 (10)
C21	0.0338 (10)	0.0386 (12)	0.0415 (11)	−0.0004 (9)	0.0053 (8)	0.0002 (9)

O4—Ca1	2.4566 (13)	C4—C5	1.385 (5)
Ca1—O3i	2.3204 (14)	C4—H4A	0.9300
Ca1—O4ii	2.3781 (14)	C5—C6	1.382 (4)
Ca1—O1W	2.3943 (17)	C5—H5A	0.9300
Ca1—O2	2.4467 (15)	C6—C7	1.487 (3)
Ca1—O5	2.4837 (17)	C8—C13	1.382 (3)
Ca1—O6	2.5628 (15)	C8—C9	1.387 (3)
Ca1—O3	2.7414 (14)	C8—H8A	0.9300
Ca1—C21	2.892 (2)	C9—C10	1.359 (4)
Ca1—C14	2.9272 (18)	C9—H9A	0.9300
O1W—Ca1	2.3944 (17)	C10—C11	1.369 (4)
O1W—H1W1	0.75 (3)	C10—H10A	0.9300
O1W—H2W1	0.89 (3)	C11—C12	1.389 (4)
O1—C7	1.309 (3)	C11—H11A	0.9300
O1—H1O	0.92 (4)	C12—C13	1.377 (3)
O2—C7	1.217 (3)	C12—H12A	0.9300
O3—C14	1.250 (2)	C13—C14	1.506 (3)
O3—Ca1	2.7414 (14)	C14—Ca1	2.9273 (18)
O4—C14	1.261 (2)	C15—C20	1.378 (3)
O4—Ca1	2.4567 (13)	C15—C16	1.394 (3)
O5—C21	1.245 (3)	C15—H15A	0.9300
O5—Ca1	2.4838 (17)	C16—C17	1.360 (4)
O6—C21	1.272 (2)	C16—H16A	0.9300
O6—Ca1	2.5628 (15)	C17—C18	1.371 (5)
C1—C6	1.364 (4)	C17—H17A	0.9300
C1—C2	1.386 (4)	C18—C19	1.383 (4)
C1—H1A	0.9300	C18—H18A	0.9300
C2—C3	1.354 (6)	C19—C20	1.384 (3)
C2—H2A	0.9300	C19—H19A	0.9300
C3—C4	1.381 (6)	C20—C21	1.498 (3)
C3—H3A	0.9300	C21—Ca1	2.892 (2)
O1W—Ca1—O2	109.84 (6)	C5—C6—C7	120.6 (2)
O1W—Ca1—O3	80.16 (5)	C1—C6—C7	119.3 (3)
O1W—Ca1—O4	89.11 (5)	C1—C6—C5	120.2 (3)
O1W—Ca1—O5	151.11 (6)	O1—C7—C6	114.0 (2)
O1W—Ca1—O6	151.97 (6)	O2—C7—C6	122.8 (2)
O2—Ca1—O3	159.31 (6)	O1—C7—O2	123.3 (2)
O2—Ca1—O4	144.90 (6)	C9—C8—C13	120.0 (2)
O2—Ca1—O5	91.65 (6)	C8—C9—C10	120.4 (3)
O2—Ca1—O6	74.00 (5)	C9—C10—C11	120.1 (2)
O3—Ca1—O4	49.51 (4)	C10—C11—C12	120.4 (3)
O3—Ca1—O5	73.72 (5)	C3—C4—H4A	120.00
O3—Ca1—O6	106.02 (4)	C5—C4—H4A	120.00
O4—Ca1—O5	83.32 (5)	C4—C5—H5A	121.00
O4—Ca1—O6	75.86 (5)	C6—C5—H5A	120.00
O5—Ca1—O6	51.43 (4)	C9—C8—H8A	120.00
C11—C12—C13	119.8 (2)	C13—C8—H8A	120.00
C8—C13—C12	119.4 (2)	C8—C9—H9A	120.00
C8—C13—C14	120.15 (18)	C10—C9—H9A	120.00
C12—C13—C14	120.46 (19)	C9—C10—H10A	120.00
O4—C14—C13	118.21 (17)	C11—C10—H10A	120.00
O3—C14—O4	121.54 (17)	C10—C11—H11A	120.00
O3—C14—C13	120.22 (17)	C12—C11—H11A	120.00
C16—C15—C20	119.9 (2)	C11—C12—H12A	120.00
C15—C16—C17	120.1 (3)	C13—C12—H12A	120.00
C16—C17—C18	120.5 (3)	C16—C15—H15A	120.00
C17—C18—C19	120.0 (3)	C20—C15—H15A	120.00
C18—C19—C20	120.0 (3)	C15—C16—H16A	120.00
C15—C20—C19	119.5 (2)	C17—C16—H16A	120.00
C15—C20—C21	120.1 (2)	C16—C17—H17A	120.00
C19—C20—C21	120.4 (2)	C18—C17—H17A	120.00
O5—C21—C20	120.62 (19)	C17—C18—H18A	120.00
O6—C21—C20	118.40 (18)	C19—C18—H18A	120.00
O5—C21—O6	120.98 (19)	C18—C19—H19A	120.00
C2—C1—H1A	120.00	C20—C19—H19A	120.00
C6—C1—H1A	120.00	Ca1—O4—C14	98.75 (11)
C1—C2—H2A	120.00	O1W—Ca1—O3i	75.71 (6)
C3—C2—H2A	121.00	O1W—Ca1—O4ii	75.41 (6)
C2—C3—H3A	119.00	O2—Ca1—O3i	87.72 (6)
C4—C3—H3A	119.00	O2—Ca1—O4ii	81.92 (6)
Ca1—O2—C7	135.25 (16)	O3—Ca1—O3i	77.05 (5)
Ca1—O3—C14	85.74 (11)	O3—Ca1—O4ii	118.58 (4)
Ca1—O5—C21	95.98 (12)	O3i—Ca1—O4	126.34 (5)
Ca1—O6—C21	91.59 (11)	O4—Ca1—O4ii	74.47 (4)
C7—O1—H1O	112 (2)	O3i—Ca1—O5	86.45 (5)
Ca1—O1W—H1W1	119 (2)	O4ii—Ca1—O5	128.29 (5)
Ca1—O1W—H2W1	115 (2)	O3i—Ca1—O6	132.20 (5)
H1W1—O1W—H2W1	99 (3)	O4ii—Ca1—O6	77.79 (5)
C2—C1—C6	120.9 (4)	O3i—Ca1—O4ii	143.74 (5)
C1—C2—C3	119.0 (4)	Ca1—O3—Ca1i	102.95 (5)
C2—C3—C4	121.1 (4)	Ca1i—O3—C14	169.26 (13)
C3—C4—C5	119.9 (5)	Ca1—O4—Ca1ii	105.53 (5)
C4—C5—C6	119.0 (4)	Ca1ii—O4—C14	151.28 (12)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1W1···O5i	0.76 (3)	2.05 (3)	2.779 (2)	163 (3)
O1—H1O···O6	0.93 (3)	1.68 (3)	2.597 (2)	167 (3)
O1W—H2W1···O6ii	0.89 (3)	1.90 (3)	2.754 (2)	159 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1W1⋯O5i	0.76 (3)	2.05 (3)	2.779 (2)	163 (3)
O1—H1O⋯O6	0.93 (3)	1.68 (3)	2.597 (2)	167 (3)
O1W—H2W1⋯O6ii	0.89 (3)	1.90 (3)	2.754 (2)	159 (3)

Symmetry codes: (i) ; (ii) .