[2-(2-Carboxy­phen­yl)benzoato]bis­(1,10-phenanthroline)zinc(II) 2-(2-carboxy­phen­yl)benzoate monohydrate

Huang, W.-W.; Yang, S.-P.

doi:10.1107/S1600536808005862

metal-organic compounds

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ISSN: 2056-9890

Volume 64| Part 4| April 2008| Pages m525-m526

doi:10.1107/S1600536808005862

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[2-(2-Carboxyphenyl)benzoato]bis(1,10-phenanthroline)zinc(II) 2-(2-carboxyphenyl)benzoate monohydrate

Wei-Wei Huang ^a and Shi-Ping Yang ^a ^*

^aSchool of Chemistry, Shanghai Normal University, Shanghai 200234, People's Republic of China
^*Correspondence e-mail: shipingy@shnu.edu.cn

(Received 29 January 2008; accepted 3 March 2008; online 7 March 2008)

In the title compound, [Zn(C₁₄H₉O₄)(C₁₂H₈N₂)₂](C₁₄H₉O₄)·H₂O, the Zn^II atom of the complex cation is six-coordinated in an octahedral geometry by four N atoms from two 1,10-phenanthroline ligands and two O atoms of a carboxylate group from a singly deprotonated diphenic acid. The phenanthroline and carboxylate ligands act as chelating ligands. The dihedral angles between the two benzene rings in the deprotonated diphenic acid groups are 81.05 (2) (ligand) and 89.10 (2)° (anion). O—H⋯O and C—H⋯O hydrogen bonds link the components into a three-dimensional network.

Related literature

For related structures containing the diphenic acid anion, see: Wan & Zhang (2003 ); Vodak et al. (2001 ); Chui et al. (2001 ); Fernandes et al. (2001 ); Trombe et al. (2002 ); Xu et al. (2003 ); Nie et al. (2001 ); Sun et al. (2001 ).

Experimental

Crystal data

[Zn(C₁₄H₉O₄)(C₁₂H₈N₂)₂](C₁₄H₉O₄)·H₂O
M_r = 926.24
Triclinic, $[P \overline 1]$
a = 10.8208 (11) Å
b = 13.7475 (14) Å
c = 14.9231 (16) Å
α = 77.824 (2)°
β = 77.294 (2)°
γ = 85.052 (2)°
V = 2115.0 (4) Å³
Z = 2
Mo Kα radiation
μ = 0.65 mm⁻¹
T = 298 (2) K
0.46 × 0.28 × 0.07 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 1998 ) T_min = 0.800, T_max = 0.960
13020 measured reflections
9403 independent reflections
4505 reflections with I > 2σ(I)
R_int = 0.103

Refinement

R[F² > 2σ(F²)] = 0.063
wR(F²) = 0.144
S = 0.82
9403 reflections
603 parameters
3 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.89 e Å⁻³
Δρ_min = −0.48 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

Zn1—O2	2.078 (3)
Zn1—N1	2.128 (3)
Zn1—N4	2.130 (3)
Zn1—N3	2.145 (4)
Zn1—N2	2.145 (3)
Zn1—O1	2.334 (3)

O2—Zn1—N1	102.73 (12)
O2—Zn1—N4	97.11 (12)
N1—Zn1—N4	100.12 (12)
O2—Zn1—N3	155.43 (11)
N1—Zn1—N3	101.83 (13)
N4—Zn1—N3	77.99 (14)
O2—Zn1—N2	94.88 (12)
N1—Zn1—N2	77.67 (12)
N4—Zn1—N2	167.99 (13)
N3—Zn1—N2	90.84 (13)
O2—Zn1—O1	59.17 (10)
N1—Zn1—O1	155.22 (11)
N4—Zn1—O1	98.98 (11)
N3—Zn1—O1	97.46 (11)
N2—Zn1—O1	86.71 (11)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O9—H9B⋯O7ⁱ	0.84 (4)	2.10 (5)	2.936 (6)	171 (6)
O4—H4B⋯O5ⁱⁱ	0.82	1.86	2.633 (5)	158
O9—H9A⋯O5	0.87 (5)	1.96 (6)	2.817 (6)	171 (7)
O8—H8B⋯O6	0.82	1.69	2.500 (5)	171
C3—H3⋯O1	0.93	2.55	3.130 (5)	121
C4—H4A⋯O6ⁱⁱ	0.93	2.42	3.221 (5)	144
C12—H12⋯O9	0.93	2.42	3.273 (6)	152
C16—H16⋯O7ⁱ	0.93	2.43	3.199 (7)	139
C19—H19⋯O6ⁱⁱⁱ	0.93	2.56	3.377 (5)	146
C22—H22⋯O1^iv	0.93	2.43	3.249 (6)	147
Symmetry codes: (i) x+1, y, z; (ii) x, y+1, z; (iii) -x+1, -y+1, -z+1; (iv) -x+1, -y+2, -z+1.

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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808005862/ci2560sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808005862/ci2560Isup2.hkl

checkCIF report

Comment top

In all types of carboxylic acids, diphenic acid is widely used in the construction of coordination polymers due to their capability of acting as bridging and chelating ligand in various coordination modes (Wan & Zhang, 2003). Much interest has been paid to the preparation of metal aromatic carboxylates under hydrothermal conditions (Vodak et al., 2001; Chui et al., 2001; Nie et al., 2001; Sun et al., 2001; Fernandes et al., 2001; Trombe et al. 2002; Xu et al. 2003). Recently, we have prepared the title compound and report here its crystal structure.

The asymmetric unit of the title compound consists of a [Zn(C₁₂H₈N₂)₂(C₁₄H₉O₄)]⁺ complex cation, one singly deprotonated diphenic acid anion (C₁₄H₉O₄^-) and one water molecule (Fig. 1). In the complex cation, the Zn^II atom is six-coordinated in an octahedral geometry by four N atoms from two 1,10-phenanthroline ligands and two O atoms of a carboxylate group from a diphenic acid, with Zn—N distances of 2.128 (3)–2.145 (4) Å and Zn—O distances of 2.078 (3) and 2.334 (3) Å. The N—Zn—N, N—Zn—O and O—Zn—O bond angles are in the ranges 77.99 (14)–167.99 (13)°, 86.71 (11)–155.23 (11)° and 59.17 (10)°, respectively (Table 1). The phenanthroline and diphenic acid act as chelating ligands (Table 1 and Fig.1). The dihedral angle between the two benzene rings in diphenic acid is ca 81.05 (2)° (cation) and 89.10 (2)° (anion).

Intermolecular O—H···O and C—H···O hydrogen bonds (Table 2) link complex cations, anions and water molecules to form a three-dimensional network (Fig. 2).

Related literature top

For related structures containing diphenic acid, see: Wan & Zhang (2003); Vodak et al. (2001); Chui et al. (2001); Fernandes et al. (2001); Trombe et al. (2002); Xu et al. (2003); Nie et al. (2001); Sun et al. (2001).

Experimental top

A mixture of diphenic acid (0.0484 g, 0.2 mmol), phenanthroline (0.04 g, 0.2 mmol), Zn(NO₃)₂.6H₂O (0.1 mmol) and NaOH (0.012 g, 0.3 mmol) with a molar ratio of 2/2/1/3 in H₂O—CH₃CH₂OH (v/v 4/1) (15 ml) was sealed in a Teflon-lined stainless steel Parr bomb. The bomb was heated to 433 K for 72 h and then cooled to room temperature at 5 K h^-1. A large amount of yellow crystals formed, which were collected by filtration, washed with water, and dried in air.

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT (Bruker, 1998); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. The asymmetric unit of the title compound, showing 30% probability displacement ellipsoids. H atoms have been omitted for clarity.
	Fig. 2. The crystal packing of the title compound, viewed down the a axis. Hydrogen bonds are shown as dashed lines.

[2-(2-Carboxyphenyl)benzoato]bis(1,10-phenanthroline)zinc(II) 2-(2-carboxyphenyl)benzoate monohydrate top

Crystal data top

[Zn(C₁₄H₉O₄)(C₁₂H₈N₂)₂](C₁₄H₉O₄)·H₂O	Z = 2
M_r = 926.24	F(000) = 956
Triclinic, P1	D_x = 1.454 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.8208 (11) Å	Cell parameters from 1630 reflections
b = 13.7475 (14) Å	θ = 4.8–40.2°
c = 14.9231 (16) Å	µ = 0.65 mm⁻¹
α = 77.824 (2)°	T = 298 K
β = 77.294 (2)°	Block, yellow
γ = 85.052 (2)°	0.46 × 0.28 × 0.07 mm
V = 2115.0 (4) Å³

Data collection top

Bruker SMART CCD area-detector diffractometer	9403 independent reflections
Radiation source: fine-focus sealed tube	4505 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.103
ϕ and ω scans	θ_max = 28.3°, θ_min = 1.5°
Absorption correction: multi-scan (SADABS; Bruker, 1998)	h = −11→14
T_min = 0.800, T_max = 0.960	k = −17→17
13020 measured reflections	l = −16→19

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)] = 0.063	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.144	H atoms treated by a mixture of independent and constrained refinement
S = 0.82	w = 1/[σ²(F_o²) + (0.0297P)²] where P = (F_o² + 2F_c²)/3
9403 reflections	(Δ/σ)_max = 0.001
603 parameters	Δρ_max = 0.89 e Å⁻³
3 restraints	Δρ_min = −0.48 e Å⁻³

Crystal data top

[Zn(C₁₄H₉O₄)(C₁₂H₈N₂)₂](C₁₄H₉O₄)·H₂O	γ = 85.052 (2)°
M_r = 926.24	V = 2115.0 (4) Å³
Triclinic, P1	Z = 2
a = 10.8208 (11) Å	Mo Kα radiation
b = 13.7475 (14) Å	µ = 0.65 mm⁻¹
c = 14.9231 (16) Å	T = 298 K
α = 77.824 (2)°	0.46 × 0.28 × 0.07 mm
β = 77.294 (2)°

Data collection top

Bruker SMART CCD area-detector diffractometer	9403 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 1998)	4505 reflections with I > 2σ(I)
T_min = 0.800, T_max = 0.960	R_int = 0.103
13020 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.063	3 restraints
wR(F²) = 0.144	H atoms treated by a mixture of independent and constrained refinement
S = 0.82	Δρ_max = 0.89 e Å⁻³
9403 reflections	Δρ_min = −0.48 e Å⁻³
603 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
Zn1	0.64423 (5)	0.88673 (4)	0.74002 (3)	0.03550 (16)
O1	0.7838 (3)	1.0069 (2)	0.64852 (19)	0.0426 (8)
O2	0.8139 (3)	0.9051 (2)	0.77676 (18)	0.0405 (7)
O3	0.7914 (4)	1.2521 (3)	0.7375 (3)	0.0767 (12)
O4	0.7058 (4)	1.3718 (3)	0.6419 (3)	0.0865 (13)
H4B	0.6644	1.3840	0.6916	0.130*
N1	0.5364 (3)	0.8073 (2)	0.8672 (2)	0.0368 (9)
N2	0.5425 (3)	1.0045 (2)	0.8031 (2)	0.0355 (8)
N3	0.5155 (3)	0.9006 (2)	0.6470 (2)	0.0366 (9)
N4	0.7090 (3)	0.7673 (2)	0.6686 (2)	0.0369 (9)
C1	0.4516 (4)	0.8671 (3)	0.9161 (3)	0.0350 (10)
C2	0.4569 (4)	0.9721 (3)	0.8828 (3)	0.0339 (10)
C3	0.5528 (4)	1.1024 (3)	0.7720 (3)	0.0469 (12)
H3	0.6133	1.1252	0.7185	0.056*
C4	0.4759 (4)	1.1718 (3)	0.8172 (3)	0.0491 (12)
H4A	0.4836	1.2396	0.7930	0.059*
C5	0.3890 (4)	1.1393 (3)	0.8973 (3)	0.0483 (12)
H5	0.3376	1.1850	0.9281	0.058*
C6	0.3773 (4)	1.0374 (3)	0.9329 (3)	0.0384 (11)
C7	0.2920 (4)	0.9964 (4)	1.0161 (3)	0.0522 (13)
H7	0.2391	1.0390	1.0499	0.063*
C8	0.2853 (4)	0.8969 (4)	1.0478 (3)	0.0514 (13)
H8A	0.2276	0.8727	1.1025	0.062*
C9	0.3653 (4)	0.8282 (3)	0.9989 (3)	0.0428 (11)
C10	0.3674 (5)	0.7248 (4)	1.0305 (3)	0.0557 (14)
H10	0.3105	0.6964	1.0841	0.067*
C11	0.4531 (5)	0.6656 (4)	0.9822 (3)	0.0609 (15)
H11	0.4568	0.5970	1.0035	0.073*
C12	0.5357 (5)	0.7098 (3)	0.9000 (3)	0.0501 (13)
H12	0.5927	0.6688	0.8670	0.060*
C13	0.5415 (4)	0.8322 (3)	0.5895 (3)	0.0365 (10)
C14	0.6448 (4)	0.7631 (3)	0.6003 (3)	0.0374 (11)
C15	0.8014 (5)	0.6997 (3)	0.6810 (3)	0.0495 (12)
H15	0.8443	0.7003	0.7285	0.059*
C16	0.8374 (5)	0.6272 (3)	0.6259 (4)	0.0617 (15)
H16	0.9042	0.5817	0.6360	0.074*
C17	0.7750 (5)	0.6236 (4)	0.5582 (4)	0.0600 (15)
H17	0.7984	0.5757	0.5213	0.072*
C18	0.6766 (5)	0.6907 (3)	0.5438 (3)	0.0482 (13)
C19	0.6023 (5)	0.6905 (4)	0.4744 (3)	0.0641 (16)
H19	0.6232	0.6450	0.4348	0.077*
C20	0.5024 (6)	0.7560 (4)	0.4665 (3)	0.0661 (16)
H20	0.4551	0.7532	0.4221	0.079*
C21	0.4670 (5)	0.8289 (4)	0.5235 (3)	0.0464 (12)
C22	0.3630 (5)	0.8974 (4)	0.5197 (3)	0.0579 (14)
H22	0.3120	0.8971	0.4771	0.070*
C23	0.3367 (5)	0.9635 (4)	0.5774 (3)	0.0518 (13)
H23	0.2673	1.0082	0.5757	0.062*
C24	0.4157 (4)	0.9631 (3)	0.6391 (3)	0.0451 (12)
H24	0.3976	1.0097	0.6777	0.054*
C25	0.8448 (4)	0.9804 (3)	0.7112 (3)	0.0355 (10)
C26	0.9559 (4)	1.0368 (3)	0.7160 (3)	0.0335 (10)
C27	1.0267 (5)	0.9982 (4)	0.7824 (3)	0.0525 (13)
H27	1.0055	0.9369	0.8210	0.063*
C28	1.1267 (5)	1.0449 (4)	0.7949 (4)	0.0639 (15)
H28	1.1724	1.0155	0.8403	0.077*
C29	1.1583 (5)	1.1361 (4)	0.7392 (4)	0.0597 (15)
H29	1.2254	1.1696	0.7464	0.072*
C30	1.0889 (5)	1.1765 (4)	0.6728 (3)	0.0545 (14)
H30	1.1105	1.2383	0.6355	0.065*
C31	0.9879 (4)	1.1300 (3)	0.6582 (3)	0.0382 (11)
C32	0.9304 (4)	1.1779 (3)	0.5740 (3)	0.0467 (12)
C33	0.9827 (5)	1.1414 (3)	0.4889 (3)	0.0505 (13)
H33	1.0407	1.0874	0.4896	0.061*
C34	0.9473 (5)	1.1854 (4)	0.4096 (4)	0.0703 (17)
H34	0.9760	1.1592	0.3558	0.084*
C35	0.8636 (5)	1.2748 (4)	0.4069 (4)	0.0711 (17)
H35	0.8431	1.3082	0.3507	0.085*
C36	0.8155 (5)	1.3089 (4)	0.4883 (3)	0.0525 (13)
H36	0.7614	1.3653	0.4875	0.063*
C37	0.8477 (5)	1.2592 (4)	0.5721 (3)	0.0515 (13)
C38	0.7835 (5)	1.2933 (4)	0.6589 (4)	0.0517 (13)
O5	0.5364 (3)	0.4416 (3)	0.7713 (2)	0.0637 (10)
O6	0.3732 (3)	0.3897 (2)	0.7279 (2)	0.0534 (9)
O7	−0.0451 (4)	0.4415 (3)	0.7539 (3)	0.0927 (13)
O8	0.1589 (4)	0.4398 (3)	0.6921 (2)	0.0643 (10)
H8B	0.2255	0.4224	0.7097	0.096*
C39	0.4238 (5)	0.4485 (3)	0.7635 (3)	0.0440 (12)
C40	0.3400 (4)	0.5330 (3)	0.7956 (3)	0.0378 (11)
C41	0.3802 (4)	0.6285 (3)	0.7610 (3)	0.0513 (13)
H41	0.4601	0.6381	0.7225	0.062*
C42	0.3053 (5)	0.7102 (3)	0.7819 (3)	0.0567 (14)
H42	0.3323	0.7743	0.7553	0.068*
C43	0.1916 (5)	0.6958 (3)	0.8416 (3)	0.0568 (14)
H43	0.1407	0.7501	0.8577	0.068*
C44	0.1511 (4)	0.5996 (3)	0.8790 (3)	0.0496 (13)
H44	0.0737	0.5904	0.9211	0.059*
C45	0.2223 (4)	0.5183 (3)	0.8554 (3)	0.0352 (10)
C46	0.1725 (4)	0.4179 (3)	0.8974 (3)	0.0373 (11)
C47	0.1929 (4)	0.3696 (3)	0.9849 (3)	0.0471 (12)
H47	0.2418	0.3994	1.0149	0.057*
C48	0.1422 (5)	0.2782 (4)	1.0288 (3)	0.0571 (14)
H48	0.1603	0.2451	1.0859	0.069*
C49	0.0635 (5)	0.2368 (4)	0.9855 (4)	0.0640 (16)
H49	0.0285	0.1757	1.0142	0.077*
C50	0.0370 (4)	0.2852 (3)	0.9012 (4)	0.0541 (14)
H50	−0.0188	0.2583	0.8746	0.065*
C51	0.0930 (4)	0.3744 (3)	0.8553 (3)	0.0431 (11)
C52	0.0630 (6)	0.4223 (4)	0.7638 (4)	0.0559 (13)
O9	0.7109 (4)	0.5128 (3)	0.8546 (3)	0.0742 (11)
H9A	0.652 (4)	0.497 (5)	0.830 (4)	0.111*
H9B	0.785 (3)	0.495 (5)	0.830 (4)	0.111*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Zn1	0.0397 (3)	0.0354 (3)	0.0325 (3)	−0.0046 (2)	−0.0036 (2)	−0.0120 (2)
O1	0.043 (2)	0.0487 (19)	0.0378 (18)	−0.0073 (15)	−0.0123 (15)	−0.0061 (15)
O2	0.0471 (19)	0.0346 (17)	0.0341 (17)	−0.0083 (14)	−0.0023 (14)	0.0018 (14)
O3	0.098 (3)	0.065 (2)	0.056 (2)	0.011 (2)	0.004 (2)	−0.014 (2)
O4	0.099 (3)	0.088 (3)	0.070 (3)	0.031 (3)	−0.016 (2)	−0.026 (2)
N1	0.049 (2)	0.030 (2)	0.033 (2)	−0.0050 (17)	−0.0075 (17)	−0.0103 (16)
N2	0.039 (2)	0.033 (2)	0.036 (2)	−0.0035 (17)	−0.0071 (17)	−0.0091 (16)
N3	0.040 (2)	0.035 (2)	0.033 (2)	−0.0099 (18)	−0.0012 (17)	−0.0070 (16)
N4	0.041 (2)	0.034 (2)	0.032 (2)	−0.0026 (18)	−0.0001 (17)	−0.0033 (16)
C1	0.037 (3)	0.038 (3)	0.033 (2)	−0.005 (2)	−0.012 (2)	−0.006 (2)
C2	0.034 (3)	0.042 (3)	0.030 (2)	−0.004 (2)	−0.0107 (19)	−0.011 (2)
C3	0.057 (3)	0.037 (3)	0.044 (3)	−0.005 (2)	−0.007 (2)	−0.007 (2)
C4	0.055 (3)	0.031 (2)	0.064 (3)	0.004 (2)	−0.014 (3)	−0.015 (2)
C5	0.046 (3)	0.048 (3)	0.058 (3)	0.010 (2)	−0.013 (2)	−0.027 (3)
C6	0.036 (3)	0.046 (3)	0.036 (3)	0.000 (2)	−0.008 (2)	−0.016 (2)
C7	0.045 (3)	0.068 (4)	0.046 (3)	0.004 (3)	−0.002 (2)	−0.027 (3)
C8	0.048 (3)	0.072 (4)	0.029 (2)	0.003 (3)	0.005 (2)	−0.013 (2)
C9	0.043 (3)	0.052 (3)	0.033 (2)	−0.011 (2)	−0.002 (2)	−0.009 (2)
C10	0.066 (4)	0.053 (3)	0.039 (3)	−0.014 (3)	0.004 (2)	0.000 (2)
C11	0.082 (4)	0.040 (3)	0.050 (3)	−0.011 (3)	0.000 (3)	0.002 (2)
C12	0.060 (3)	0.042 (3)	0.046 (3)	−0.005 (3)	−0.009 (2)	−0.006 (2)
C13	0.043 (3)	0.035 (2)	0.029 (2)	−0.013 (2)	−0.002 (2)	−0.0024 (19)
C14	0.042 (3)	0.040 (3)	0.028 (2)	−0.013 (2)	0.003 (2)	−0.008 (2)
C15	0.057 (3)	0.048 (3)	0.037 (3)	0.004 (3)	−0.003 (2)	−0.003 (2)
C16	0.065 (4)	0.037 (3)	0.065 (4)	0.012 (3)	0.010 (3)	−0.003 (3)
C17	0.076 (4)	0.045 (3)	0.054 (3)	−0.009 (3)	0.014 (3)	−0.024 (3)
C18	0.056 (3)	0.046 (3)	0.041 (3)	−0.014 (3)	0.008 (2)	−0.019 (2)
C19	0.080 (4)	0.077 (4)	0.041 (3)	−0.026 (3)	0.003 (3)	−0.031 (3)
C20	0.074 (4)	0.095 (5)	0.038 (3)	−0.028 (4)	−0.009 (3)	−0.026 (3)
C21	0.053 (3)	0.055 (3)	0.031 (3)	−0.024 (3)	−0.009 (2)	0.001 (2)
C22	0.060 (4)	0.072 (4)	0.043 (3)	−0.030 (3)	−0.022 (3)	0.008 (3)
C23	0.049 (3)	0.053 (3)	0.052 (3)	−0.010 (3)	−0.016 (3)	0.002 (3)
C24	0.041 (3)	0.043 (3)	0.051 (3)	−0.007 (2)	−0.008 (2)	−0.007 (2)
C25	0.031 (3)	0.039 (3)	0.039 (3)	0.006 (2)	−0.004 (2)	−0.020 (2)
C26	0.031 (3)	0.037 (2)	0.033 (2)	0.004 (2)	−0.0042 (19)	−0.012 (2)
C27	0.054 (3)	0.055 (3)	0.047 (3)	−0.005 (3)	−0.012 (3)	−0.006 (2)
C28	0.055 (4)	0.080 (4)	0.064 (4)	−0.013 (3)	−0.026 (3)	−0.015 (3)
C29	0.038 (3)	0.084 (4)	0.067 (4)	−0.015 (3)	−0.006 (3)	−0.035 (3)
C30	0.050 (3)	0.058 (3)	0.059 (3)	−0.016 (3)	−0.003 (3)	−0.021 (3)
C31	0.032 (3)	0.046 (3)	0.038 (2)	−0.004 (2)	−0.002 (2)	−0.017 (2)
C32	0.034 (3)	0.035 (3)	0.067 (3)	−0.013 (2)	0.003 (2)	−0.012 (2)
C33	0.064 (4)	0.049 (3)	0.034 (3)	−0.013 (3)	0.005 (2)	−0.008 (2)
C34	0.056 (4)	0.098 (5)	0.051 (4)	−0.003 (3)	0.008 (3)	−0.022 (3)
C35	0.074 (4)	0.090 (5)	0.050 (3)	−0.019 (4)	−0.013 (3)	−0.007 (3)
C36	0.057 (3)	0.063 (3)	0.037 (3)	−0.014 (3)	−0.009 (2)	−0.003 (2)
C37	0.049 (3)	0.053 (3)	0.051 (3)	−0.018 (3)	0.007 (2)	−0.019 (3)
C38	0.063 (4)	0.052 (3)	0.042 (3)	−0.013 (3)	0.000 (3)	−0.019 (3)
O5	0.039 (2)	0.078 (3)	0.076 (2)	0.0133 (19)	−0.0019 (18)	−0.038 (2)
O6	0.065 (2)	0.0467 (19)	0.050 (2)	0.0005 (17)	−0.0018 (17)	−0.0241 (16)
O7	0.067 (3)	0.101 (3)	0.114 (4)	0.006 (3)	−0.042 (3)	−0.009 (3)
O8	0.076 (3)	0.073 (3)	0.048 (2)	−0.005 (2)	−0.021 (2)	−0.0099 (18)
C39	0.046 (3)	0.044 (3)	0.036 (3)	0.002 (2)	0.005 (2)	−0.009 (2)
C40	0.042 (3)	0.034 (2)	0.035 (2)	−0.003 (2)	0.001 (2)	−0.010 (2)
C41	0.047 (3)	0.048 (3)	0.052 (3)	−0.009 (3)	0.009 (2)	−0.011 (2)
C42	0.064 (4)	0.034 (3)	0.062 (3)	−0.010 (3)	0.008 (3)	−0.007 (2)
C43	0.058 (4)	0.034 (3)	0.072 (4)	0.005 (2)	0.006 (3)	−0.018 (2)
C44	0.045 (3)	0.039 (3)	0.053 (3)	0.001 (2)	0.015 (2)	−0.010 (2)
C45	0.033 (3)	0.034 (2)	0.038 (2)	−0.001 (2)	−0.002 (2)	−0.0104 (19)
C46	0.036 (3)	0.034 (2)	0.037 (3)	0.001 (2)	0.004 (2)	−0.008 (2)
C47	0.046 (3)	0.048 (3)	0.040 (3)	0.004 (2)	0.005 (2)	−0.009 (2)
C48	0.058 (4)	0.054 (3)	0.044 (3)	0.012 (3)	0.012 (3)	−0.004 (3)
C49	0.071 (4)	0.035 (3)	0.065 (4)	−0.001 (3)	0.025 (3)	−0.002 (3)
C50	0.048 (3)	0.039 (3)	0.073 (4)	−0.010 (2)	0.002 (3)	−0.018 (3)
C51	0.044 (3)	0.032 (2)	0.049 (3)	−0.002 (2)	0.000 (2)	−0.009 (2)
C52	0.060 (4)	0.045 (3)	0.066 (4)	0.002 (3)	−0.023 (3)	−0.010 (3)
O9	0.089 (3)	0.065 (3)	0.071 (3)	−0.009 (3)	−0.008 (2)	−0.024 (2)

Geometric parameters (Å, º) top

Zn1—O2	2.078 (3)	C23—C24	1.387 (6)
Zn1—N1	2.128 (3)	C23—H23	0.93
Zn1—N4	2.130 (3)	C24—H24	0.93
Zn1—N3	2.145 (4)	C25—C26	1.507 (5)
Zn1—N2	2.145 (3)	C26—C27	1.375 (6)
Zn1—O1	2.334 (3)	C26—C31	1.409 (6)
Zn1—C25	2.528 (4)	C27—C28	1.371 (6)
O1—C25	1.237 (5)	C27—H27	0.93
O2—C25	1.276 (5)	C28—C29	1.374 (7)
O3—C38	1.207 (5)	C28—H28	0.93
O4—C38	1.326 (6)	C29—C30	1.370 (6)
O4—H4B	0.82	C29—H29	0.93
N1—C12	1.327 (5)	C30—C31	1.391 (6)
N1—C1	1.370 (5)	C30—H30	0.93
N2—C3	1.333 (5)	C31—C32	1.525 (6)
N2—C2	1.355 (5)	C32—C37	1.369 (6)
N3—C24	1.331 (5)	C32—C33	1.446 (6)
N3—C13	1.373 (5)	C33—C34	1.331 (6)
N4—C15	1.321 (5)	C33—H33	0.93
N4—C14	1.366 (5)	C34—C35	1.462 (7)
C1—C9	1.409 (5)	C34—H34	0.93
C1—C2	1.426 (5)	C35—C36	1.374 (6)
C2—C6	1.405 (5)	C35—H35	0.93
C3—C4	1.394 (6)	C36—C37	1.394 (6)
C3—H3	0.93	C36—H36	0.93
C4—C5	1.366 (6)	C37—C38	1.478 (6)
C4—H4A	0.93	O5—C39	1.243 (5)
C5—C6	1.394 (6)	O6—C39	1.274 (5)
C5—H5	0.93	O7—C52	1.211 (6)
C6—C7	1.415 (5)	O8—C52	1.314 (6)
C7—C8	1.353 (6)	O8—H8B	0.82
C7—H7	0.93	C39—C40	1.503 (6)
C8—C9	1.430 (6)	C40—C41	1.376 (6)
C8—H8A	0.93	C40—C45	1.389 (5)
C9—C10	1.400 (6)	C41—C42	1.377 (6)
C10—C11	1.365 (6)	C41—H41	0.93
C10—H10	0.93	C42—C43	1.353 (6)
C11—C12	1.403 (6)	C42—H42	0.93
C11—H11	0.93	C43—C44	1.390 (6)
C12—H12	0.93	C43—H43	0.93
C13—C21	1.414 (6)	C44—C45	1.365 (5)
C13—C14	1.418 (6)	C44—H44	0.93
C14—C18	1.410 (6)	C45—C46	1.484 (5)
C15—C16	1.401 (6)	C46—C47	1.390 (6)
C15—H15	0.93	C46—C51	1.407 (6)
C16—C17	1.343 (7)	C47—C48	1.387 (6)
C16—H16	0.93	C47—H47	0.93
C17—C18	1.370 (7)	C48—C49	1.395 (7)
C17—H17	0.93	C48—H48	0.93
C18—C19	1.444 (7)	C49—C50	1.371 (7)
C19—C20	1.356 (7)	C49—H49	0.93
C19—H19	0.93	C50—C51	1.389 (6)
C20—C21	1.423 (6)	C50—H50	0.93
C20—H20	0.93	C51—C52	1.477 (6)
C21—C22	1.406 (7)	O9—H9A	0.87 (5)
C22—C23	1.351 (6)	O9—H9B	0.84 (2)
C22—H22	0.93

O2—Zn1—N1	102.73 (12)	C23—C22—C21	120.6 (5)
O2—Zn1—N4	97.11 (12)	C23—C22—H22	119.7
N1—Zn1—N4	100.12 (12)	C21—C22—H22	119.7
O2—Zn1—N3	155.43 (11)	C22—C23—C24	118.4 (5)
N1—Zn1—N3	101.83 (13)	C22—C23—H23	120.8
N4—Zn1—N3	77.99 (14)	C24—C23—H23	120.8
O2—Zn1—N2	94.88 (12)	N3—C24—C23	124.5 (4)
N1—Zn1—N2	77.67 (12)	N3—C24—H24	117.8
N4—Zn1—N2	167.99 (13)	C23—C24—H24	117.8
N3—Zn1—N2	90.84 (13)	O1—C25—O2	121.2 (4)
O2—Zn1—O1	59.17 (10)	O1—C25—C26	122.0 (4)
N1—Zn1—O1	155.22 (11)	O2—C25—C26	116.7 (4)
N4—Zn1—O1	98.98 (11)	O1—C25—Zn1	66.7 (2)
N3—Zn1—O1	97.46 (11)	O2—C25—Zn1	55.0 (2)
N2—Zn1—O1	86.71 (11)	C26—C25—Zn1	167.7 (3)
O2—Zn1—C25	30.21 (12)	C27—C26—C31	117.9 (4)
N1—Zn1—C25	129.98 (14)	C27—C26—C25	119.0 (4)
N4—Zn1—C25	101.56 (13)	C31—C26—C25	123.1 (4)
N3—Zn1—C25	126.52 (13)	C28—C27—C26	123.7 (5)
N2—Zn1—C25	88.57 (12)	C28—C27—H27	118.1
O1—Zn1—C25	29.12 (11)	C26—C27—H27	118.1
C25—O1—Zn1	84.2 (2)	C27—C28—C29	118.9 (5)
C25—O2—Zn1	94.8 (3)	C27—C28—H28	120.6
C38—O4—H4B	109.5	C29—C28—H28	120.6
C12—N1—C1	118.0 (4)	C30—C29—C28	118.6 (5)
C12—N1—Zn1	128.5 (3)	C30—C29—H29	120.7
C1—N1—Zn1	113.3 (3)	C28—C29—H29	120.7
C3—N2—C2	118.5 (4)	C29—C30—C31	123.6 (5)
C3—N2—Zn1	127.8 (3)	C29—C30—H30	118.2
C2—N2—Zn1	113.7 (3)	C31—C30—H30	118.2
C24—N3—C13	117.3 (4)	C30—C31—C26	117.4 (4)
C24—N3—Zn1	129.6 (3)	C30—C31—C32	117.4 (4)
C13—N3—Zn1	113.1 (3)	C26—C31—C32	124.8 (4)
C15—N4—C14	117.6 (4)	C37—C32—C33	120.0 (5)
C15—N4—Zn1	129.0 (3)	C37—C32—C31	124.1 (4)
C14—N4—Zn1	113.5 (3)	C33—C32—C31	115.4 (4)
N1—C1—C9	122.2 (4)	C34—C33—C32	119.6 (5)
N1—C1—C2	117.6 (4)	C34—C33—H33	120.2
C9—C1—C2	120.1 (4)	C32—C33—H33	120.2
N2—C2—C6	122.6 (4)	C33—C34—C35	120.2 (5)
N2—C2—C1	117.1 (4)	C33—C34—H34	119.9
C6—C2—C1	120.3 (4)	C35—C34—H34	119.9
N2—C3—C4	122.2 (4)	C36—C35—C34	119.2 (5)
N2—C3—H3	118.9	C36—C35—H35	120.4
C4—C3—H3	118.9	C34—C35—H35	120.4
C5—C4—C3	119.4 (4)	C35—C36—C37	120.2 (5)
C5—C4—H4A	120.3	C35—C36—H36	119.9
C3—C4—H4A	120.3	C37—C36—H36	119.9
C4—C5—C6	120.0 (4)	C32—C37—C36	120.7 (4)
C4—C5—H5	120.0	C32—C37—C38	121.5 (5)
C6—C5—H5	120.0	C36—C37—C38	117.7 (5)
C5—C6—C2	117.3 (4)	O3—C38—O4	122.4 (5)
C5—C6—C7	124.3 (4)	O3—C38—C37	125.5 (5)
C2—C6—C7	118.4 (4)	O4—C38—C37	111.9 (5)
C8—C7—C6	121.8 (4)	C52—O8—H8B	109.5
C8—C7—H7	119.1	O5—C39—O6	124.5 (4)
C6—C7—H7	119.1	O5—C39—C40	119.0 (4)
C7—C8—C9	121.3 (4)	O6—C39—C40	116.4 (4)
C7—C8—H8A	119.3	C41—C40—C45	119.1 (4)
C9—C8—H8A	119.3	C41—C40—C39	118.3 (4)
C10—C9—C1	117.8 (4)	C45—C40—C39	122.5 (4)
C10—C9—C8	124.1 (4)	C40—C41—C42	121.8 (4)
C1—C9—C8	118.0 (4)	C40—C41—H41	119.1
C11—C10—C9	119.8 (4)	C42—C41—H41	119.1
C11—C10—H10	120.1	C43—C42—C41	118.9 (4)
C9—C10—H10	120.1	C43—C42—H42	120.5
C10—C11—C12	119.1 (5)	C41—C42—H42	120.5
C10—C11—H11	120.5	C42—C43—C44	119.9 (4)
C12—C11—H11	120.5	C42—C43—H43	120.0
N1—C12—C11	123.1 (4)	C44—C43—H43	120.0
N1—C12—H12	118.5	C45—C44—C43	121.5 (4)
C11—C12—H12	118.5	C45—C44—H44	119.2
N3—C13—C21	121.7 (4)	C43—C44—H44	119.2
N3—C13—C14	117.4 (4)	C44—C45—C40	118.6 (4)
C21—C13—C14	120.9 (4)	C44—C45—C46	118.6 (4)
N4—C14—C18	121.7 (4)	C40—C45—C46	122.8 (4)
N4—C14—C13	117.9 (4)	C47—C46—C51	118.4 (4)
C18—C14—C13	120.4 (4)	C47—C46—C45	119.9 (4)
N4—C15—C16	122.8 (5)	C51—C46—C45	121.3 (4)
N4—C15—H15	118.6	C48—C47—C46	121.7 (5)
C16—C15—H15	118.6	C48—C47—H47	119.2
C17—C16—C15	119.6 (5)	C46—C47—H47	119.2
C17—C16—H16	120.2	C47—C48—C49	118.6 (5)
C15—C16—H16	120.2	C47—C48—H48	120.7
C16—C17—C18	119.9 (5)	C49—C48—H48	120.7
C16—C17—H17	120.1	C50—C49—C48	120.8 (5)
C18—C17—H17	120.1	C50—C49—H49	119.6
C17—C18—C14	118.5 (5)	C48—C49—H49	119.6
C17—C18—C19	123.5 (5)	C49—C50—C51	120.3 (5)
C14—C18—C19	118.0 (5)	C49—C50—H50	119.8
C20—C19—C18	120.6 (5)	C51—C50—H50	119.8
C20—C19—H19	119.7	C50—C51—C46	120.0 (5)
C18—C19—H19	119.7	C50—C51—C52	118.0 (5)
C19—C20—C21	122.5 (5)	C46—C51—C52	121.9 (4)
C19—C20—H20	118.7	O7—C52—O8	121.0 (5)
C21—C20—H20	118.7	O7—C52—C51	121.9 (5)
C22—C21—C13	117.5 (4)	O8—C52—C51	117.0 (5)
C22—C21—C20	125.0 (5)	H9A—O9—H9B	115 (6)
C13—C21—C20	117.5 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O9—H9B···O7ⁱ	0.84 (4)	2.10 (5)	2.936 (6)	171 (6)
O4—H4B···O5ⁱⁱ	0.82	1.86	2.633 (5)	158
O9—H9A···O5	0.87 (5)	1.96 (6)	2.817 (6)	171 (7)
O8—H8B···O6	0.82	1.69	2.500 (5)	171
C3—H3···O1	0.93	2.55	3.130 (5)	121
C4—H4A···O6ⁱⁱ	0.93	2.42	3.221 (5)	144
C12—H12···O9	0.93	2.42	3.273 (6)	152
C16—H16···O7ⁱ	0.93	2.43	3.199 (7)	139
C19—H19···O6ⁱⁱⁱ	0.93	2.56	3.377 (5)	146
C22—H22···O1^iv	0.93	2.43	3.249 (6)	147

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

Experimental details

Crystal data
Chemical formula	[Zn(C₁₄H₉O₄)(C₁₂H₈N₂)₂](C₁₄H₉O₄)·H₂O
M_r	926.24
Crystal system, space group	Triclinic, P1
Temperature (K)	298
a, b, c (Å)	10.8208 (11), 13.7475 (14), 14.9231 (16)
α, β, γ (°)	77.824 (2), 77.294 (2), 85.052 (2)
V (Å³)	2115.0 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.65
Crystal size (mm)	0.46 × 0.28 × 0.07

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 1998)
T_min, T_max	0.800, 0.960
No. of measured, independent and observed [I > 2σ(I)] reflections	13020, 9403, 4505
R_int	0.103
(sin θ/λ)_max (Å⁻¹)	0.668

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.063, 0.144, 0.82
No. of reflections	9403
No. of parameters	603
No. of restraints	3
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.89, −0.48

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1998), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected geometric parameters (Å, º) top

Zn1—O2	2.078 (3)	Zn1—N3	2.145 (4)
Zn1—N1	2.128 (3)	Zn1—N2	2.145 (3)
Zn1—N4	2.130 (3)	Zn1—O1	2.334 (3)

O2—Zn1—N1	102.73 (12)	N4—Zn1—N2	167.99 (13)
O2—Zn1—N4	97.11 (12)	N3—Zn1—N2	90.84 (13)
N1—Zn1—N4	100.12 (12)	O2—Zn1—O1	59.17 (10)
O2—Zn1—N3	155.43 (11)	N1—Zn1—O1	155.22 (11)
N1—Zn1—N3	101.83 (13)	N4—Zn1—O1	98.98 (11)
N4—Zn1—N3	77.99 (14)	N3—Zn1—O1	97.46 (11)
O2—Zn1—N2	94.88 (12)	N2—Zn1—O1	86.71 (11)
N1—Zn1—N2	77.67 (12)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O9—H9B···O7ⁱ	0.84 (4)	2.10 (5)	2.936 (6)	171 (6)
O4—H4B···O5ⁱⁱ	0.82	1.86	2.633 (5)	158
O9—H9A···O5	0.87 (5)	1.96 (6)	2.817 (6)	171 (7)
O8—H8B···O6	0.82	1.69	2.500 (5)	171
C3—H3···O1	0.93	2.55	3.130 (5)	121
C4—H4A···O6ⁱⁱ	0.93	2.42	3.221 (5)	144
C12—H12···O9	0.93	2.42	3.273 (6)	152
C16—H16···O7ⁱ	0.93	2.43	3.199 (7)	139
C19—H19···O6ⁱⁱⁱ	0.93	2.56	3.377 (5)	146
C22—H22···O1^iv	0.93	2.43	3.249 (6)	147

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

Acknowledgements

The authors acknowledge financial support from the Science and Technology Foundation of Shanghai (grant No. 065212050) and the Foundation of Shanghai Higher Education (grant No. 07ZZ68).

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Volume 64| Part 4| April 2008| Pages m525-m526

doi:10.1107/S1600536808005862

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metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

[2-(2-Carb­oxy­phen­yl)benzoato]bis­­(1,10-phenanthroline)zinc(II) 2-(2-carb­oxy­phen­yl)benzoate monohydrate

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Experimental

Crystal data

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metal-organic compounds

[2-(2-Carboxyphenyl)benzoato]bis(1,10-phenanthroline)zinc(II) 2-(2-carboxyphenyl)benzoate monohydrate