catena-Poly[[[aqua-(1,10-phenanthro-line)zinc(II)]-μ-3,3'-(p-phenyl-ene)di-acrylato] hemihydrate].

In the title compound, {[Zn(C(12)H(8)O(4))(C(12)H(8)N(2))(H(2)O)]·0.5H(2)O}(n), each Zn(II) atom is six-coordinated by two N atoms from one 1,10-phenanthroline (phen), three carboxyl-ate O atoms from two different L ligands [H(2)L = 3,3'-(p-phenyl-ene)diacrylic acid] and one water mol-ecule in a distorted octa-hedral environment. The two L dianions are situated across inversion centres and bridge neighbouring Zn(II) centres, yielding a chain propagating parallel to [100]. O-H⋯O hydrogen bonds between the coordinated water molecule, the solvent water molecule (half-occupied) and the carboxylate O atoms further stabilize the structure.

Related literature

For general background and related structures see: Wang et al. (2008 ▶). For related literature, see: Batten & Robson (1998 ▶).

Experimental

Crystal data

[Zn(C12H8O4)(C12H8N2)(H2O)]·0.5H2O

M = 488.78

Triclinic,

a = 8.959 (5) Å

b = 11.505 (5) Å

c = 11.691 (5) Å

α = 67.219 (5)°

β = 76.434 (5)°

γ = 89.555 (5)°

V = 1075.4 (9) Å3

Z = 2

Mo Kα radiation

μ = 1.18 mm−1

T = 293 K

0.30 × 0.22 × 0.19 mm

Data collection

Bruker APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.701, T max = 0.792

6674 measured reflections

3887 independent reflections

3193 reflections with I > 2σ(I)

R int = 0.019

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.101

S = 0.98

3887 reflections

312 parameters

6 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.90 e Å−3

Δρmin = −0.24 e Å−3

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT (Bruker, 1998 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809025665/at2836sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809025665/at2836Isup2.hkl

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

[Zn(C12H8O4)(C12H8N2)(H2O)]·0.5H2O	Z = 2
Mr = 488.78	F(000) = 502
Triclinic, P1	Dx = 1.509 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.959 (5) Å	Cell parameters from 3887 reflections
b = 11.505 (5) Å	θ = 3.0–25.4°
c = 11.691 (5) Å	µ = 1.18 mm−1
α = 67.219 (5)°	T = 293 K
β = 76.434 (5)°	Block, colourless
γ = 89.555 (5)°	0.30 × 0.22 × 0.19 mm
V = 1075.4 (9) Å3

Bruker APEX CCD area-detector diffractometer	3887 independent reflections
Radiation source: fine-focus sealed tube	3193 reflections with I > 2σ(I)
graphite	Rint = 0.019
φ and ω scans	θmax = 25.4°, θmin = 4.2°
Absorption correction: multi-scan (SADABS; Sheldrick 1996)	h = −10→9
Tmin = 0.701, Tmax = 0.792	k = −11→13
6674 measured reflections	l = −12→14

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.101	H atoms treated by a mixture of independent and constrained refinement
S = 0.98	w = 1/[σ2(Fo2) + (0.0712P)2] where P = (Fo2 + 2Fc2)/3
3887 reflections	(Δ/σ)max < 0.001
312 parameters	Δρmax = 0.90 e Å−3
6 restraints	Δρmin = −0.24 e Å−3

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 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 > 2sigma(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	Occ. (<1)
Zn1	0.22324 (4)	0.16358 (3)	0.84090 (3)	0.02776 (13)
O1W	0.1608 (2)	−0.02160 (18)	0.87917 (19)	0.0326 (4)
O2	0.1060 (3)	0.0767 (2)	1.1643 (2)	0.0512 (6)
O3	−0.0271 (2)	0.20043 (17)	0.88909 (18)	0.0391 (5)
O4	0.1579 (2)	0.3439 (2)	0.8484 (2)	0.0469 (5)
O1	0.3082 (3)	0.1033 (2)	0.99979 (18)	0.0429 (5)
N2	0.1984 (3)	0.2138 (2)	0.6449 (2)	0.0311 (5)
N1	0.4515 (3)	0.2360 (2)	0.7226 (2)	0.0310 (5)
C24	0.0755 (4)	0.1957 (3)	0.6072 (3)	0.0397 (7)
H24	−0.0132	0.1519	0.6694	0.048*
C4	0.4100 (3)	0.0176 (2)	1.4115 (3)	0.0312 (6)
C12	−0.4743 (3)	0.6175 (2)	0.9997 (3)	0.0302 (6)
H12	−0.4565	0.6976	0.9986	0.036*
C18	0.3274 (3)	0.2775 (2)	0.5531 (2)	0.0293 (6)
C16	0.5967 (4)	0.3587 (3)	0.5039 (3)	0.0398 (7)
C21	0.3323 (4)	0.3264 (3)	0.4225 (3)	0.0385 (7)
C10	−0.3744 (3)	0.4296 (2)	0.9805 (2)	0.0262 (6)
C14	0.7138 (4)	0.3119 (3)	0.6779 (4)	0.0529 (9)
H14	0.7988	0.3171	0.7092	0.064*
C3	0.3115 (4)	0.0349 (3)	1.3225 (3)	0.0338 (6)
H3	0.2058	0.0276	1.3575	0.041*
C2	0.3556 (4)	0.0593 (3)	1.1999 (3)	0.0350 (7)
H2	0.4604	0.0638	1.1629	0.042*
C9	−0.2477 (3)	0.3549 (2)	0.9552 (3)	0.0298 (6)
H9	−0.2753	0.2706	0.9736	0.036*
C5	0.5685 (4)	0.0473 (3)	1.3708 (3)	0.0398 (7)
H5	0.6161	0.0793	1.2835	0.048*
C6	0.6565 (4)	0.0305 (3)	1.4563 (3)	0.0387 (7)
H6	0.7624	0.0515	1.4259	0.046*
C11	−0.3509 (3)	0.5488 (2)	0.9820 (2)	0.0303 (6)
H11	−0.2517	0.5818	0.9709	0.036*
C17	0.4611 (3)	0.2916 (2)	0.5953 (2)	0.0297 (6)
C15	0.7236 (4)	0.3696 (3)	0.5503 (4)	0.0506 (9)
H15	0.8145	0.4161	0.4941	0.061*
C8	−0.0978 (3)	0.3927 (3)	0.9090 (3)	0.0333 (6)
H8	−0.0641	0.4748	0.8939	0.040*
C22	0.2003 (4)	0.3045 (3)	0.3869 (3)	0.0466 (8)
H22	0.1996	0.3345	0.3009	0.056*
C23	0.0726 (4)	0.2386 (3)	0.4800 (3)	0.0467 (8)
H23	−0.0160	0.2227	0.4578	0.056*
C1	0.2466 (4)	0.0804 (2)	1.1161 (3)	0.0345 (7)
C7	0.0161 (3)	0.3079 (3)	0.8811 (3)	0.0335 (6)
C19	0.5968 (4)	0.4111 (3)	0.3712 (3)	0.0491 (9)
H19	0.6851	0.4579	0.3107	0.059*
C20	0.4736 (4)	0.3944 (3)	0.3323 (3)	0.0499 (9)
H20	0.4788	0.4273	0.2450	0.060*
C13	0.5761 (4)	0.2450 (3)	0.7616 (3)	0.0412 (7)
H13	0.5717	0.2052	0.8486	0.049*
O2W	−0.0410 (4)	0.2769 (3)	1.2193 (3)	0.0270 (8)	0.50
HW22	−0.121 (4)	0.275 (5)	1.198 (6)	0.040*	0.50
HW21	0.008 (5)	0.223 (4)	1.202 (6)	0.040*	0.50
HW12	0.073 (4)	−0.019 (4)	0.863 (4)	0.090 (16)*
HW11	0.144 (4)	−0.074 (3)	0.958 (2)	0.057 (11)*

	U11	U22	U33	U12	U13	U23
Zn1	0.0284 (2)	0.03257 (19)	0.02057 (18)	0.00310 (12)	−0.00688 (12)	−0.00830 (13)
O1W	0.0300 (12)	0.0337 (10)	0.0290 (11)	−0.0016 (8)	−0.0075 (9)	−0.0067 (9)
O2	0.0353 (13)	0.0729 (15)	0.0441 (13)	−0.0072 (11)	−0.0161 (10)	−0.0180 (11)
O3	0.0455 (13)	0.0329 (11)	0.0309 (10)	0.0078 (9)	0.0001 (9)	−0.0098 (8)
O4	0.0272 (12)	0.0614 (13)	0.0518 (13)	0.0078 (10)	−0.0054 (10)	−0.0248 (11)
O1	0.0513 (14)	0.0539 (12)	0.0247 (10)	0.0023 (10)	−0.0200 (9)	−0.0108 (9)
N2	0.0305 (13)	0.0360 (12)	0.0228 (11)	−0.0001 (10)	−0.0064 (9)	−0.0075 (10)
N1	0.0310 (13)	0.0360 (12)	0.0299 (12)	0.0063 (10)	−0.0095 (10)	−0.0163 (10)
C24	0.0337 (17)	0.0485 (17)	0.0344 (16)	0.0003 (13)	−0.0104 (13)	−0.0127 (14)
C4	0.0380 (16)	0.0340 (14)	0.0255 (14)	0.0037 (12)	−0.0135 (12)	−0.0127 (11)
C12	0.0329 (15)	0.0255 (13)	0.0314 (14)	0.0005 (11)	−0.0048 (12)	−0.0121 (11)
C18	0.0350 (16)	0.0266 (13)	0.0222 (13)	0.0042 (11)	−0.0046 (11)	−0.0068 (11)
C16	0.0352 (17)	0.0350 (15)	0.0423 (17)	−0.0020 (13)	0.0037 (13)	−0.0156 (13)
C21	0.0473 (19)	0.0384 (15)	0.0242 (14)	0.0083 (13)	−0.0073 (13)	−0.0076 (12)
C10	0.0280 (14)	0.0278 (13)	0.0205 (12)	0.0010 (11)	−0.0044 (11)	−0.0080 (10)
C14	0.0295 (17)	0.077 (2)	0.068 (2)	0.0018 (16)	−0.0132 (16)	−0.044 (2)
C3	0.0356 (16)	0.0383 (15)	0.0292 (15)	0.0011 (12)	−0.0137 (12)	−0.0120 (12)
C2	0.0378 (17)	0.0386 (15)	0.0290 (15)	0.0000 (13)	−0.0164 (13)	−0.0093 (12)
C9	0.0318 (15)	0.0277 (13)	0.0287 (14)	0.0045 (11)	−0.0086 (12)	−0.0091 (11)
C5	0.0402 (18)	0.0584 (18)	0.0192 (13)	0.0004 (14)	−0.0079 (12)	−0.0131 (13)
C6	0.0285 (15)	0.0572 (18)	0.0306 (15)	0.0006 (13)	−0.0088 (12)	−0.0168 (14)
C11	0.0246 (14)	0.0360 (14)	0.0287 (14)	−0.0022 (11)	−0.0028 (11)	−0.0133 (12)
C17	0.0324 (15)	0.0270 (13)	0.0272 (14)	0.0011 (11)	−0.0030 (12)	−0.0105 (11)
C15	0.0322 (18)	0.0564 (19)	0.061 (2)	−0.0060 (15)	0.0019 (15)	−0.0283 (17)
C8	0.0313 (16)	0.0324 (14)	0.0348 (15)	0.0032 (12)	−0.0077 (12)	−0.0121 (12)
C22	0.057 (2)	0.0567 (19)	0.0252 (15)	0.0122 (16)	−0.0152 (15)	−0.0119 (14)
C23	0.046 (2)	0.065 (2)	0.0369 (17)	0.0091 (16)	−0.0225 (15)	−0.0210 (15)
C1	0.0420 (19)	0.0300 (14)	0.0300 (15)	−0.0061 (12)	−0.0169 (13)	−0.0056 (12)
C7	0.0347 (17)	0.0369 (16)	0.0229 (14)	0.0073 (12)	−0.0059 (12)	−0.0065 (12)
C19	0.044 (2)	0.0462 (18)	0.0369 (17)	−0.0047 (15)	0.0089 (15)	−0.0064 (14)
C20	0.059 (2)	0.0505 (18)	0.0210 (14)	0.0018 (16)	0.0035 (15)	−0.0014 (13)
C13	0.0371 (17)	0.0548 (18)	0.0437 (17)	0.0104 (14)	−0.0172 (14)	−0.0282 (15)
O2W	0.029 (2)	0.0325 (19)	0.0288 (19)	0.0005 (15)	−0.0180 (16)	−0.0163 (16)

Zn1—O1	2.041 (2)	C21—C20	1.442 (5)
Zn1—O1W	2.053 (2)	C10—C11	1.396 (4)
Zn1—N1	2.144 (3)	C10—C12ii	1.397 (4)
Zn1—O4	2.180 (2)	C10—C9	1.462 (4)
Zn1—N2	2.202 (2)	C14—C15	1.359 (5)
Zn1—O3	2.260 (2)	C14—C13	1.392 (5)
Zn1—C7	2.563 (3)	C14—H14	0.9300
O1W—HW12	0.85 (3)	C3—C2	1.309 (4)
O1W—HW11	0.86 (2)	C3—H3	0.9300
O2—C1	1.246 (4)	C2—C1	1.494 (4)
O3—C7	1.260 (4)	C2—H2	0.9300
O4—C7	1.261 (4)	C9—C8	1.331 (4)
O1—C1	1.263 (4)	C9—H9	0.9300
N2—C24	1.324 (4)	C5—C6	1.369 (4)
N2—C18	1.360 (4)	C5—H5	0.9300
N1—C13	1.320 (4)	C6—C4i	1.401 (4)
N1—C17	1.355 (4)	C6—H6	0.9300
C24—C23	1.380 (4)	C11—H11	0.9300
C24—H24	0.9300	C15—H15	0.9300
C4—C5	1.388 (4)	C8—C7	1.475 (4)
C4—C6i	1.401 (4)	C8—H8	0.9300
C4—C3	1.472 (4)	C22—C23	1.363 (5)
C12—C11	1.378 (4)	C22—H22	0.9300
C12—C10ii	1.397 (4)	C23—H23	0.9300
C12—H12	0.9300	C19—C20	1.329 (5)
C18—C21	1.398 (4)	C19—H19	0.9300
C18—C17	1.431 (4)	C20—H20	0.9300
C16—C15	1.395 (5)	C13—H13	0.9300
C16—C17	1.407 (4)	O2W—HW22	0.815 (10)
C16—C19	1.431 (5)	O2W—HW21	0.816 (10)
C21—C22	1.396 (5)
O1—Zn1—O1W	89.22 (9)	C15—C14—H14	120.1
O1—Zn1—N1	89.76 (9)	C13—C14—H14	120.1
O1W—Zn1—N1	115.47 (8)	C2—C3—C4	127.5 (3)
O1—Zn1—O4	96.13 (9)	C2—C3—H3	116.2
O1W—Zn1—O4	149.07 (9)	C4—C3—H3	116.2
N1—Zn1—O4	95.05 (8)	C3—C2—C1	123.6 (3)
O1—Zn1—N2	162.97 (9)	C3—C2—H2	118.2
O1W—Zn1—N2	88.25 (8)	C1—C2—H2	118.2
N1—Zn1—N2	76.20 (9)	C8—C9—C10	128.0 (3)
O4—Zn1—N2	94.67 (9)	C8—C9—H9	116.0
O1—Zn1—O3	111.13 (9)	C10—C9—H9	116.0
O1W—Zn1—O3	90.77 (8)	C6—C5—C4	121.4 (3)
N1—Zn1—O3	147.13 (8)	C6—C5—H5	119.3
O4—Zn1—O3	58.87 (8)	C4—C5—H5	119.3
N2—Zn1—O3	85.75 (8)	C5—C6—C4i	121.3 (3)
O1—Zn1—C7	104.70 (9)	C5—C6—H6	119.3
O1W—Zn1—C7	119.90 (9)	C4i—C6—H6	119.3
N1—Zn1—C7	122.57 (9)	C12—C11—C10	120.2 (3)
O4—Zn1—C7	29.45 (9)	C12—C11—H11	119.9
N2—Zn1—C7	91.12 (9)	C10—C11—H11	119.9
O3—Zn1—C7	29.44 (8)	N1—C17—C16	123.0 (3)
Zn1—O1W—HW12	104 (3)	N1—C17—C18	117.7 (2)
Zn1—O1W—HW11	116 (2)	C16—C17—C18	119.2 (3)
HW12—O1W—HW11	104 (3)	C14—C15—C16	119.7 (3)
C7—O3—Zn1	88.74 (18)	C14—C15—H15	120.1
C7—O4—Zn1	92.34 (18)	C16—C15—H15	120.1
C1—O1—Zn1	132.4 (2)	C9—C8—C7	121.7 (3)
C24—N2—C18	117.9 (2)	C9—C8—H8	119.1
C24—N2—Zn1	128.96 (19)	C7—C8—H8	119.1
C18—N2—Zn1	113.08 (18)	C23—C22—C21	119.1 (3)
C13—N1—C17	118.0 (3)	C23—C22—H22	120.4
C13—N1—Zn1	126.8 (2)	C21—C22—H22	120.4
C17—N1—Zn1	114.67 (18)	C22—C23—C24	119.6 (3)
N2—C24—C23	123.2 (3)	C22—C23—H23	120.2
N2—C24—H24	118.4	C24—C23—H23	120.2
C23—C24—H24	118.4	O2—C1—O1	125.7 (3)
C5—C4—C6i	117.2 (3)	O2—C1—C2	118.7 (3)
C5—C4—C3	123.0 (3)	O1—C1—C2	115.5 (3)
C6i—C4—C3	119.8 (3)	O3—C7—O4	120.0 (3)
C11—C12—C10ii	121.8 (2)	O3—C7—C8	120.6 (3)
C11—C12—H12	119.1	O4—C7—C8	119.4 (3)
C10ii—C12—H12	119.1	O3—C7—Zn1	61.82 (15)
N2—C18—C21	122.3 (3)	O4—C7—Zn1	58.21 (16)
N2—C18—C17	117.1 (2)	C8—C7—Zn1	176.5 (2)
C21—C18—C17	120.6 (3)	C20—C19—C16	121.5 (3)
C15—C16—C17	116.9 (3)	C20—C19—H19	119.2
C15—C16—C19	124.2 (3)	C16—C19—H19	119.2
C17—C16—C19	118.9 (3)	C19—C20—C21	121.4 (3)
C22—C21—C18	117.9 (3)	C19—C20—H20	119.3
C22—C21—C20	123.8 (3)	C21—C20—H20	119.3
C18—C21—C20	118.3 (3)	N1—C13—C14	122.6 (3)
C11—C10—C12ii	118.0 (2)	N1—C13—H13	118.7
C11—C10—C9	122.8 (2)	C14—C13—H13	118.7
C12ii—C10—C9	119.1 (2)	HW22—O2W—HW21	105.6 (18)
C15—C14—C13	119.8 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—HW12···O2iii	0.85 (3)	1.87 (3)	2.687 (3)	158 (4)
O1W—HW11···O3iii	0.86 (2)	1.88 (3)	2.685 (3)	155 (3)
O2W—HW21···O2	0.82 (1)	2.04 (1)	2.856 (5)	173 (5)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—HW12⋯O2i	0.85 (3)	1.87 (3)	2.687 (3)	158 (4)
O1W—HW11⋯O3i	0.86 (2)	1.88 (3)	2.685 (3)	155 (3)
O2W—HW21⋯O2	0.816 (10)	2.044 (14)	2.856 (5)	173 (5)

Symmetry code: (i) .