catena-Poly[[diaqua­bis(diphenyl­acetato)­zinc(II)]-μ-4,4′-bipyridine]

Yu, S.-S.; Zhou, H.; Xian, H.; Tian, Z.-F.

doi:10.1107/S1600536809004450

catena-Poly[[diaquabis(diphenylacetato)zinc(II)]-μ-4,4′-bipyridine]

S.-S. Yu, H. Zhou, H. Xian and Z.-F. Tian

In the title compound, [Zn(C₁₄H₁₁O₂)₂(C₁₀H₈N₂)(H₂O)₂]_n, the Zn^II ion lies on a crystallographic inversion center and is in a slightly distorted octahedral coordination enviroment. 4,4′-Bipyridine ligands act as bridging ligands, connecting Zn^II ions into a chain along the b-axis direction. In the crystal structure, these chains are linked by intermolecular O—H

O hydrogen bonds to form a two-dimensional network parallel to the ab plane.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536809004450/lh2759sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536809004450/lh2759Isup2.hkl Contains datablock I

CCDC reference: 705360

checkCIF report

Key indicators

Single-crystal X-ray study
T = 291 K
Mean (C-C) = 0.007 Å
R factor = 0.061
wR factor = 0.135
Data-to-parameter ratio = 12.5

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT230_ALERT_2_B Hirshfeld Test Diff for    C3     --  C4      ..       8.53 su
PLAT230_ALERT_2_B Hirshfeld Test Diff for    C10    --  C11     ..       7.06 su

Alert level C
            Value of measurement temperature given =   291.000
            Value of melting point given =     0.000
PLAT230_ALERT_2_C Hirshfeld Test Diff for    O1     --  C14     ..       6.39 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C2     --  C3      ..       5.68 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C5     --  C6      ..       5.67 su
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Zn1    --  O1      ..       5.12 su
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Zn1    --  O3      ..       5.71 su
PLAT341_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...          7
PLAT234_ALERT_4_C Large Hirshfeld Difference N1     --  C15     ..       0.14  Ang.
PLAT234_ALERT_4_C Large Hirshfeld Difference N1     --  C19     ..       0.13  Ang.
PLAT234_ALERT_4_C Large Hirshfeld Difference C6     --  C7      ..       0.10  Ang.
PLAT234_ALERT_4_C Large Hirshfeld Difference C8     --  C9      ..       0.13  Ang.
PLAT234_ALERT_4_C Large Hirshfeld Difference C11    --  C12     ..       0.10  Ang.
PLAT234_ALERT_4_C Large Hirshfeld Difference C16    --  C17     ..       0.12  Ang.
PLAT234_ALERT_4_C Large Hirshfeld Difference C18    --  C19     ..       0.12  Ang.

   0 ALERT level A = In general: serious problem
   2 ALERT level B = Potentially serious problem
  13 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
   7 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   7 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Comment top

During the past decade, the design of new metal-organic supramolecular solids has attracted attention in the fields of coordination chemistry and crystal engineering, for the sake of developing desired crystalline materials with potential functionality (Moulton & Zaworotko, 2001; Janiak , 2003). Furthermore, it has been realised that weak noncovalent interactions such as hydrogen bonds, aromatic stacking, and van der Waals forces (Hosseini, 2005; Nishio, 2004) are crucial in the direction of such crystalline architectures. Hitherto, a variety of organic connectors containing pyridyl and/or carboxylate groups (Brammer, 2004) have been widely used to construct metal-organic supramolecular frameworks. Herein we report the crystal structure of the title compound (1).

The asymmetric unit of (I) is illustrated in Fig. 1. The structure of (I) is a one-dimensional chain (Fig. 2), in which the Zn^II ions are coordinated by two O atoms from two monodentate carboxylate groups of two bis(diphenylacetato) ligands, two N atoms of two bridging 4,4'-bipyridine ligands and two O atoms from two water molecules. The Zn^II ion is in a slightly distorted octahedral coordination environment. In the crystal structure, these one-dimensional chains are linked via intermolecular O—H···O hydrogen bonds to form a two-dimensional network.

Related literature top

For background information, see: Janiak (2003); Moulton & Zaworotko (2001); Brammer (2004). For the role of weak noncovalent interactions in crystalline architectures, see: Hosseini (2005); Nishio (2004). Please check added text.

Experimental top

Soild ZnCl₂(136 mg, 1 mmol), 4,4'-bipyridine (1 mmol, 0.156 g) and diphenylacetic acid (212 mg, 1 mmol) in water (8 ml) was placed in a Teflon-lined stainless-steel Parr bomb that was heated at 433 K for 48 h. Colorless block crystals were collected after the bomb was subsequently allowed to cool to room temperature.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The asymmetric unit of (I), showing displacement ellipsoids at the 30% probability level.
	Fig. 2. Part of the one-dimensional chain structure of (I).

catena-Poly[[diaquabis(diphenylacetato)zinc(II)]-µ-4,4'-bipyridine] top

Crystal data top

[Zn(C₁₄H₁₁O₂)₂(C₁₀H₈N₂)(H₂O)₂]	Z = 1
M_r = 680.04	F(000) = 354
Triclinic, P1	D_x = 1.460 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.7536 (13) Å	Cell parameters from 924 reflections
b = 11.882 (3) Å	θ = 2.2–20.2°
c = 12.229 (3) Å	µ = 0.85 mm⁻¹
α = 98.522 (4)°	T = 291 K
β = 103.273 (5)°	Block, colorless
γ = 103.450 (4)°	0.30 × 0.26 × 0.24 mm
V = 773.2 (3) Å³

Data collection top

Bruker SMART CCD diffractometer	2679 independent reflections
Radiation source: fine-focus sealed tube	2234 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.022
ϕ and ω scans	θ_max = 25.0°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −6→6
T_min = 0.785, T_max = 0.823	k = −12→14
3891 measured reflections	l = −14→11

Refinement top

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)] = 0.061	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.135	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.05P)² + 1.22P] where P = (F_o² + 2F_c²)/3
2679 reflections	(Δ/σ)_max < 0.001
214 parameters	Δρ_max = 0.23 e Å⁻³
0 restraints	Δρ_min = −0.22 e Å⁻³

Crystal data top

[Zn(C₁₄H₁₁O₂)₂(C₁₀H₈N₂)(H₂O)₂]	γ = 103.450 (4)°
M_r = 680.04	V = 773.2 (3) Å³
Triclinic, P1	Z = 1
a = 5.7536 (13) Å	Mo Kα radiation
b = 11.882 (3) Å	µ = 0.85 mm⁻¹
c = 12.229 (3) Å	T = 291 K
α = 98.522 (4)°	0.30 × 0.26 × 0.24 mm
β = 103.273 (5)°

Data collection top

Bruker SMART CCD diffractometer	2679 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	2234 reflections with I > 2σ(I)
T_min = 0.785, T_max = 0.823	R_int = 0.022
3891 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.061	0 restraints
wR(F²) = 0.135	H-atom parameters constrained
S = 1.02	Δρ_max = 0.23 e Å⁻³
2679 reflections	Δρ_min = −0.22 e Å⁻³
214 parameters

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.5242 (9)	0.7816 (4)	−0.0135 (4)	0.0552 (12)
H1	0.6390	0.7442	0.0197	0.066*
C2	0.4992 (9)	0.7953 (4)	−0.1250 (4)	0.0575 (12)
H2	0.5969	0.7669	−0.1672	0.069*
C3	0.3272 (9)	0.8519 (4)	−0.1754 (4)	0.0540 (11)
H3	0.3106	0.8614	−0.2507	0.065*
C4	0.1819 (9)	0.8936 (4)	−0.1118 (4)	0.0592 (13)
H4	0.0679	0.9317	−0.1441	0.071*
C5	0.2073 (8)	0.8782 (4)	0.0000 (4)	0.0481 (11)
H5	0.1076	0.9052	0.0418	0.058*
C6	0.3773 (8)	0.8238 (4)	0.0501 (4)	0.0544 (12)
C7	0.3955 (8)	0.8080 (4)	0.1714 (4)	0.0528 (12)
H7	0.2720	0.8423	0.1963	0.063*
C8	0.3306 (8)	0.6802 (4)	0.1832 (4)	0.0550 (12)
C9	0.0736 (9)	0.6218 (4)	0.1441 (4)	0.0588 (13)
H9	−0.0450	0.6615	0.1215	0.071*
C10	0.0081 (9)	0.4974 (4)	0.1416 (4)	0.0575 (13)
H10	−0.1592	0.4555	0.1163	0.069*
C11	0.1787 (9)	0.4365 (5)	0.1745 (4)	0.0557 (12)
H11	0.1303	0.3552	0.1695	0.067*
C12	0.4204 (8)	0.4999 (4)	0.2145 (4)	0.0527 (11)
H12	0.5387	0.4609	0.2393	0.063*
C13	0.4981 (10)	0.6189 (4)	0.2200 (4)	0.0552 (12)
H13	0.6662	0.6588	0.2489	0.066*
C14	0.6538 (8)	0.8770 (4)	0.2592 (4)	0.0463 (11)
C15	1.1601 (9)	0.7492 (4)	0.4541 (4)	0.0494 (11)
H15	1.2639	0.7935	0.4184	0.059*
C16	1.1620 (8)	0.6347 (4)	0.4540 (4)	0.0478 (11)
H16	1.2728	0.6045	0.4222	0.057*
C17	1.0046 (9)	0.5634 (4)	0.4995 (4)	0.0510 (11)
C18	0.8504 (9)	0.6187 (4)	0.5508 (4)	0.0489 (11)
H18	0.7424	0.5755	0.5853	0.059*
C19	0.8580 (9)	0.7341 (4)	0.5501 (4)	0.0476 (11)
H19	0.7515	0.7669	0.5829	0.057*
N1	1.0118 (8)	0.8015 (3)	0.5046 (4)	0.0591 (10)
O1	0.6471 (6)	0.9293 (3)	0.3557 (3)	0.0600 (9)
O2	0.8431 (5)	0.8730 (3)	0.2284 (3)	0.0516 (8)
O3	1.2454 (6)	1.0195 (3)	0.3733 (3)	0.0608 (9)
H3B	1.1539	0.9696	0.2994	0.073*
H3C	1.3925	0.9961	0.4024	0.073*
Zn1	1.0000	1.0000	0.5000	0.0473 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.053 (3)	0.063 (3)	0.046 (3)	0.020 (2)	0.004 (2)	0.010 (2)
C2	0.053 (3)	0.059 (3)	0.055 (3)	0.003 (2)	0.026 (2)	0.001 (2)
C3	0.051 (3)	0.056 (3)	0.049 (3)	0.008 (2)	0.010 (2)	0.011 (2)
C4	0.053 (3)	0.051 (3)	0.065 (3)	0.011 (2)	−0.007 (2)	0.028 (2)
C5	0.047 (2)	0.046 (2)	0.055 (3)	0.024 (2)	0.008 (2)	0.012 (2)
C6	0.046 (3)	0.052 (3)	0.061 (3)	0.014 (2)	0.012 (2)	0.004 (2)
C7	0.044 (2)	0.061 (3)	0.045 (2)	0.018 (2)	0.001 (2)	0.000 (2)
C8	0.042 (2)	0.051 (3)	0.056 (3)	0.002 (2)	0.006 (2)	−0.008 (2)
C9	0.062 (3)	0.057 (3)	0.050 (3)	0.000 (2)	0.016 (2)	0.013 (2)
C10	0.053 (3)	0.059 (3)	0.048 (3)	−0.013 (2)	0.024 (2)	0.005 (2)
C11	0.060 (3)	0.063 (3)	0.048 (3)	0.018 (2)	0.028 (2)	0.001 (2)
C12	0.049 (3)	0.049 (3)	0.065 (3)	0.016 (2)	0.018 (2)	0.020 (2)
C13	0.063 (3)	0.057 (3)	0.051 (3)	0.019 (2)	0.019 (2)	0.019 (2)
C14	0.039 (2)	0.045 (2)	0.047 (2)	0.0136 (18)	0.0069 (19)	−0.0099 (19)
C15	0.061 (3)	0.047 (3)	0.058 (3)	0.030 (2)	0.027 (2)	0.026 (2)
C16	0.051 (3)	0.057 (3)	0.054 (3)	0.032 (2)	0.025 (2)	0.026 (2)
C17	0.059 (3)	0.043 (2)	0.056 (3)	0.025 (2)	0.015 (2)	0.011 (2)
C18	0.054 (3)	0.058 (3)	0.049 (2)	0.030 (2)	0.019 (2)	0.021 (2)
C19	0.056 (3)	0.041 (2)	0.050 (3)	0.023 (2)	0.010 (2)	0.017 (2)
N1	0.065 (3)	0.044 (2)	0.064 (3)	0.0170 (19)	0.011 (2)	0.0041 (19)
O1	0.0470 (18)	0.067 (2)	0.057 (2)	0.0143 (16)	0.0080 (15)	−0.0010 (16)
O2	0.0419 (17)	0.0550 (19)	0.0550 (18)	0.0178 (14)	0.0141 (14)	−0.0054 (14)
O3	0.058 (2)	0.056 (2)	0.061 (2)	0.0140 (16)	0.0108 (16)	0.0031 (16)
Zn1	0.0440 (4)	0.0420 (4)	0.0436 (4)	0.0021 (3)	0.0025 (3)	0.0020 (3)

Geometric parameters (Å, º) top

C1—C2	1.377 (6)	C12—H12	0.9300
C1—C6	1.398 (6)	C13—H13	0.9300
C1—H1	0.9300	C14—O2	1.240 (5)
C2—C3	1.401 (7)	C14—O1	1.263 (5)
C2—H2	0.9300	C15—C16	1.363 (6)
C3—C4	1.388 (7)	C15—N1	1.368 (6)
C3—H3	0.9300	C15—H15	0.9300
C4—C5	1.385 (6)	C16—C17	1.365 (6)
C4—H4	0.9300	C16—H16	0.9300
C5—C6	1.374 (6)	C17—C18	1.420 (6)
C5—H5	0.9300	C17—C17ⁱ	1.497 (8)
C6—C7	1.505 (7)	C18—C19	1.362 (6)
C7—C8	1.514 (7)	C18—H18	0.9300
C7—C14	1.572 (6)	C19—N1	1.328 (6)
C7—H7	0.9800	C19—H19	0.9300
C8—C13	1.373 (7)	N1—Zn1	2.384 (4)
C8—C9	1.413 (6)	O1—Zn1	2.250 (3)
C9—C10	1.432 (7)	O3—Zn1	2.326 (3)
C9—H9	0.9300	O3—H3B	0.9600
C10—C11	1.372 (7)	O3—H3C	0.9600
C10—H10	0.9300	Zn1—O1ⁱⁱ	2.250 (3)
C11—C12	1.354 (7)	Zn1—O3ⁱⁱ	2.326 (3)
C11—H11	0.9300	Zn1—N1ⁱⁱ	2.384 (4)
C12—C13	1.367 (6)

C2—C1—C6	120.1 (5)	C8—C13—H13	119.7
C2—C1—H1	120.0	O2—C14—O1	126.4 (4)
C6—C1—H1	120.0	O2—C14—C7	117.4 (4)
C1—C2—C3	120.3 (5)	O1—C14—C7	116.2 (4)
C1—C2—H2	119.9	C16—C15—N1	122.6 (4)
C3—C2—H2	119.9	C16—C15—H15	118.7
C4—C3—C2	119.3 (4)	N1—C15—H15	118.7
C4—C3—H3	120.3	C15—C16—C17	121.4 (4)
C2—C3—H3	120.3	C15—C16—H16	119.3
C5—C4—C3	119.8 (4)	C17—C16—H16	119.3
C5—C4—H4	120.1	C16—C17—C18	115.3 (4)
C3—C4—H4	120.1	C16—C17—C17ⁱ	123.8 (5)
C6—C5—C4	121.1 (5)	C18—C17—C17ⁱ	120.9 (5)
C6—C5—H5	119.4	C19—C18—C17	121.1 (4)
C4—C5—H5	119.4	C19—C18—H18	119.4
C5—C6—C1	119.4 (5)	C17—C18—H18	119.4
C5—C6—C7	119.0 (4)	N1—C19—C18	122.5 (4)
C1—C6—C7	121.6 (4)	N1—C19—H19	118.8
C6—C7—C8	114.4 (4)	C18—C19—H19	118.8
C6—C7—C14	113.9 (4)	C19—N1—C15	117.1 (4)
C8—C7—C14	109.1 (4)	C19—N1—Zn1	120.2 (3)
C6—C7—H7	106.3	C15—N1—Zn1	122.6 (3)
C8—C7—H7	106.3	C14—O1—Zn1	119.4 (3)
C14—C7—H7	106.3	Zn1—O3—H3B	109.4
C13—C8—C9	120.2 (5)	Zn1—O3—H3C	109.2
C13—C8—C7	125.6 (4)	H3B—O3—H3C	109.5
C9—C8—C7	114.0 (4)	O1—Zn1—O1ⁱⁱ	180.000 (1)
C8—C9—C10	115.4 (5)	O1—Zn1—O3	92.45 (12)
C8—C9—H9	122.3	O1ⁱⁱ—Zn1—O3	87.55 (12)
C10—C9—H9	122.3	O1—Zn1—O3ⁱⁱ	87.55 (12)
C11—C10—C9	123.6 (5)	O1ⁱⁱ—Zn1—O3ⁱⁱ	92.45 (12)
C11—C10—H10	118.2	O3—Zn1—O3ⁱⁱ	180.000 (1)
C9—C10—H10	118.2	O1—Zn1—N1ⁱⁱ	90.93 (13)
C12—C11—C10	117.1 (5)	O1ⁱⁱ—Zn1—N1ⁱⁱ	89.07 (13)
C12—C11—H11	121.4	O3—Zn1—N1ⁱⁱ	86.86 (13)
C10—C11—H11	121.4	O3ⁱⁱ—Zn1—N1ⁱⁱ	93.14 (13)
C11—C12—C13	122.8 (5)	O1—Zn1—N1	89.07 (13)
C11—C12—H12	118.6	O1ⁱⁱ—Zn1—N1	90.93 (13)
C13—C12—H12	118.6	O3—Zn1—N1	93.14 (13)
C12—C13—C8	120.7 (5)	O3ⁱⁱ—Zn1—N1	86.86 (13)
C12—C13—H13	119.7	N1ⁱⁱ—Zn1—N1	180.000 (2)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3B···O2	0.96	1.82	2.618 (5)	139
O3—H3C···O1ⁱⁱⁱ	0.96	1.97	2.802 (5)	143

Symmetry code: (iii) x+1, y, z.

Experimental details

Crystal data
Chemical formula	[Zn(C₁₄H₁₁O₂)₂(C₁₀H₈N₂)(H₂O)₂]
M_r	680.04
Crystal system, space group	Triclinic, P1
Temperature (K)	291
a, b, c (Å)	5.7536 (13), 11.882 (3), 12.229 (3)
α, β, γ (°)	98.522 (4), 103.273 (5), 103.450 (4)
V (Å³)	773.2 (3)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	0.85
Crystal size (mm)	0.30 × 0.26 × 0.24

Data collection
Diffractometer	Bruker SMART CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.785, 0.823
No. of measured, independent and observed [I > 2σ(I)] reflections	3891, 2679, 2234
R_int	0.022
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.061, 0.135, 1.02
No. of reflections	2679
No. of parameters	214
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.23, −0.22

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXTL (Sheldrick, 2008).