Tetra­aqua­(1,10-phenanthroline)zinc(II) 3,6-dicarboxy­bicyclo­[2.2.2]oct-7-ene-2,5-dicarboxyl­ate

Yu, C.-H.

doi:10.1107/S1600536808025622

metal-organic compounds

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ISSN: 2056-9890

Volume 64| Part 9| September 2008| Page m1158

doi:10.1107/S1600536808025622

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Tetraaqua(1,10-phenanthroline)zinc(II) 3,6-dicarboxybicyclo[2.2.2]oct-7-ene-2,5-dicarboxylate

Chun-Hui Yu ^a ^*

^aDepartment of Chemistry, College of Chemistry and Biology, Beihua University, Jilin City 132013, People's Republic of China
^*Correspondence e-mail: jlschy@126.com

(Received 7 August 2008; accepted 8 August 2008; online 13 August 2008)

In the title compound, [Zn(C₁₂H₈N₂)(H₂O)₄](C₁₂H₁₀O₈), each Zn^II atom is six-coordinated by two N atoms from one phenanthroline molecule and by four O atoms from four water molecules in a distorted octahedral environment. In the crystal structure, ions are linked by O—H⋯O hydrogen bonds.

Related literature

For related literature, see: Ma et al. (2003 ); Hu (2008 ).

Experimental

Crystal data

[Zn(C₁₂H₈N₂)(H₂O)₄](C₁₂H₁₀O₈)
M_r = 599.84
Monoclinic, P 2₁ /c
a = 7.4550 (2) Å
b = 13.5991 (4) Å
c = 22.9833 (7) Å
β = 91.555 (1)°
V = 2329.22 (12) Å³
Z = 4
Mo Kα radiation
μ = 1.13 mm⁻¹
T = 293 (2) K
0.33 × 0.22 × 0.19 mm

Data collection

Bruker APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SAINT; Bruker, 1998 ) T_min = 0.687, T_max = 0.805
14301 measured reflections
5626 independent reflections
3854 reflections with I > 2σ(I)
R_int = 0.048

Refinement

R[F² > 2σ(F²)] = 0.046
wR(F²) = 0.122
S = 0.96
5626 reflections
382 parameters
12 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.50 e Å⁻³
Δρ_min = −0.59 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3⋯O8ⁱ	0.82	1.88	2.674 (3)	163
O6—H6A⋯O2ⁱⁱ	0.82	1.84	2.583 (3)	151
O2W—HW22⋯O2ⁱⁱⁱ	0.799 (17)	2.06 (2)	2.818 (3)	158 (4)
O4W—HW41⋯O1	0.845 (18)	1.86 (2)	2.705 (3)	174 (4)
O2W—HW21⋯O8^iv	0.809 (17)	2.121 (18)	2.904 (3)	163 (4)
O4W—HW42⋯O7^iv	0.811 (17)	1.876 (17)	2.686 (3)	177 (3)
O1W—HW12⋯O7^v	0.816 (17)	2.09 (2)	2.884 (3)	165 (3)
O1W—HW11⋯O2^vi	0.826 (18)	2.13 (2)	2.923 (3)	160 (4)
O3W—HW31⋯O2^vi	0.80 (4)	2.57 (4)	3.233 (4)	142 (5)
Symmetry codes: (i) $[-x, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (ii) $[-x+1, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (iii) -x, -y, -z+1; (iv) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (v) $[x-1, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (vi) x-1, y, z.

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 global, I. DOI: 10.1107/S1600536808025622/bt2766sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808025622/bt2766Isup2.hkl

checkCIF report

Comment top

Recently, complexes with poly(carboxylic acids) have been investigated in the area of solid state and material science (Ma et al., 2003). I selected bicyclo[2.2.2]oct-7-ene-2,3,5,6-tetracarboxylic acid (H₄L) as a poly(carboxylic acid) ligand and phenanthroline (phen) as a secondary ligand, generating a new complex, [Zn(phen)(H₂O)₄]^.[H₂L], which is reported here.

In the title compound, [Zn(phen)(H₂O)₄]^.[H₂L], each Zn^II atom is six-coordinated by two N atoms from one phen molecule, and four O atoms from four water molecules in a distorted octahedral environment. Each H₂L^2- acts as a counter-anion. In the crystal, the molecules are linked by O—H···O hydrogen bonds.

Related literature top

For related literature, see: Ma et al. (2003); Hu (2008).

Experimental top

A mixture of H₄L (0.5 mmol), phen (0.5 mmol), NaOH (1 mmol) and ZnCl₂^.6H₂O (0.5 mmol) was suspended in 12 ml of deionized water and sealed in a 20-ml Teflon-lined autoclave. Upon heating at 140°C for one week, the autoclave was slowly cooled to room temperature. The crystals were collected, washed with deionized water and dried.

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 structure of the title compound, showing the atomic numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.

Tetraaqua(1,10-phenanthroline)zinc(II) 3,6-dicarboxybicyclo[2.2.2]oct-7-ene-2,5-dicarboxylate top

Crystal data top

[Zn(C₁₂H₈N₂)(H₂O)₄](C₁₂H₁₀O₈)	F(000) = 1240
M_r = 599.84	D_x = 1.711 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5626 reflections
a = 7.4550 (2) Å	θ = 1.1–28.3°
b = 13.5991 (4) Å	µ = 1.13 mm⁻¹
c = 22.9833 (7) Å	T = 293 K
β = 91.555 (1)°	Block, colorless
V = 2329.22 (12) Å³	0.33 × 0.22 × 0.19 mm
Z = 4

Data collection top

Bruker APEX CCD area-detector diffractometer	5626 independent reflections
Radiation source: fine-focus sealed tube	3854 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.048
ϕ and ω scans	θ_max = 28.3°, θ_min = 1.7°
Absorption correction: multi-scan (SAINT; Bruker, 1998)	h = −9→8
T_min = 0.687, T_max = 0.805	k = −14→18
14301 measured reflections	l = −29→30

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.122	H atoms treated by a mixture of independent and constrained refinement
S = 0.96	w = 1/[σ²(F_o²) + (0.0613P)²] where P = (F_o² + 2F_c²)/3
5626 reflections	(Δ/σ)_max < 0.001
382 parameters	Δρ_max = 0.50 e Å⁻³
12 restraints	Δρ_min = −0.59 e Å⁻³

Crystal data top

[Zn(C₁₂H₈N₂)(H₂O)₄](C₁₂H₁₀O₈)	V = 2329.22 (12) Å³
M_r = 599.84	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 7.4550 (2) Å	µ = 1.13 mm⁻¹
b = 13.5991 (4) Å	T = 293 K
c = 22.9833 (7) Å	0.33 × 0.22 × 0.19 mm
β = 91.555 (1)°

Data collection top

Bruker APEX CCD area-detector diffractometer	5626 independent reflections
Absorption correction: multi-scan (SAINT; Bruker, 1998)	3854 reflections with I > 2σ(I)
T_min = 0.687, T_max = 0.805	R_int = 0.048
14301 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	12 restraints
wR(F²) = 0.122	H atoms treated by a mixture of independent and constrained refinement
S = 0.96	Δρ_max = 0.50 e Å⁻³
5626 reflections	Δρ_min = −0.59 e Å⁻³
382 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	−0.2556 (4)	0.2855 (2)	0.61401 (12)	0.0348 (7)
H1	−0.2529	0.2264	0.6344	0.042*
C2	−0.2659 (4)	0.3745 (3)	0.64532 (13)	0.0414 (8)
H2	−0.2708	0.3734	0.6857	0.050*
C4	−0.2686 (5)	0.4609 (3)	0.61680 (15)	0.0459 (9)
H4	−0.2756	0.5194	0.6376	0.055*
C5	−0.2610 (5)	0.4632 (2)	0.55588 (14)	0.0399 (8)
C6	−0.2629 (6)	0.5510 (2)	0.52184 (18)	0.0570 (10)
H6	−0.2628	0.6117	0.5405	0.068*
C7	−0.2648 (6)	0.5479 (2)	0.46388 (18)	0.0554 (10)
H7	−0.2692	0.6064	0.4430	0.067*
C8	−0.2603 (5)	0.4564 (2)	0.43289 (15)	0.0385 (8)
C9	−0.2666 (4)	0.4472 (2)	0.37212 (14)	0.0409 (8)
H9	−0.2727	0.5032	0.3489	0.049*
C10	−0.2639 (4)	0.3579 (2)	0.34720 (13)	0.0377 (8)
H10	−0.2694	0.3523	0.3069	0.045*
C11	−0.2527 (4)	0.2731 (2)	0.38191 (12)	0.0307 (7)
H11	−0.2502	0.2118	0.3641	0.037*
C12	−0.2538 (4)	0.3703 (2)	0.52783 (12)	0.0272 (6)
C13	−0.2518 (4)	0.3674 (2)	0.46512 (12)	0.0271 (6)
C14	0.1068 (4)	0.06219 (19)	0.70078 (12)	0.0268 (6)
C15	0.2475 (4)	0.12469 (19)	0.73318 (11)	0.0220 (6)
H15	0.3295	0.0808	0.7548	0.026*
C16	0.3605 (4)	0.19231 (18)	0.69329 (10)	0.0206 (5)
H16	0.4869	0.1784	0.7027	0.025*
C17	0.3320 (4)	0.1720 (2)	0.62817 (11)	0.0252 (6)
C18	0.3279 (3)	0.30060 (18)	0.70964 (10)	0.0187 (5)
H18	0.3894	0.3445	0.6829	0.022*
C19	0.1500 (4)	0.19201 (18)	0.77770 (11)	0.0209 (5)
H19	0.0744	0.1524	0.8029	0.025*
C20	0.0380 (4)	0.26442 (19)	0.74361 (11)	0.0243 (6)
H20	−0.0857	0.2692	0.7469	0.029*
C021	0.2081 (4)	0.3018 (2)	0.86562 (11)	0.0234 (6)
C21	0.1303 (4)	0.32112 (19)	0.70833 (11)	0.0245 (6)
H21	0.0773	0.3693	0.6849	0.029*
C22	0.4016 (4)	0.31473 (18)	0.77246 (11)	0.0211 (5)
H22	0.5246	0.2892	0.7732	0.025*
C23	0.4151 (4)	0.4227 (2)	0.79029 (11)	0.0262 (6)
C25	0.2936 (4)	0.24790 (18)	0.81443 (10)	0.0216 (6)
H25	0.3771	0.1990	0.8309	0.026*
N1	−0.2458 (3)	0.27831 (16)	0.43985 (9)	0.0246 (5)
N2	−0.2495 (3)	0.28378 (17)	0.55612 (9)	0.0255 (5)
O1	0.2699 (3)	0.23710 (15)	0.59560 (8)	0.0417 (6)
O2	0.3860 (3)	0.08866 (14)	0.60983 (8)	0.0348 (5)
O1W	−0.4920 (3)	0.13197 (19)	0.49279 (10)	0.0375 (5)
O3	0.1019 (3)	−0.02720 (15)	0.72076 (9)	0.0469 (6)
H3	0.0255	−0.0587	0.7024	0.070*
O2W	−0.1668 (4)	0.06205 (18)	0.43708 (11)	0.0422 (6)
O4	0.0122 (3)	0.09170 (16)	0.66157 (10)	0.0473 (6)
O3W	−0.2116 (4)	0.0585 (2)	0.56396 (12)	0.0490 (6)
O5	0.3699 (3)	0.49114 (14)	0.76039 (9)	0.0399 (5)
O4W	0.0517 (3)	0.17941 (19)	0.50606 (9)	0.0401 (6)
O6	0.4927 (3)	0.42964 (15)	0.84189 (8)	0.0374 (5)
H6A	0.4995	0.4877	0.8514	0.056*
O7	0.2531 (3)	0.27139 (14)	0.91541 (8)	0.0336 (5)
O8	0.0968 (3)	0.36877 (15)	0.85579 (8)	0.0371 (5)
Zn1	−0.22063 (5)	0.16487 (2)	0.499735 (13)	0.02916 (12)
HW22	−0.223 (4)	0.013 (2)	0.4325 (16)	0.063 (13)*
HW41	0.113 (5)	0.198 (3)	0.5355 (10)	0.095*
HW21	−0.092 (4)	0.069 (3)	0.4124 (14)	0.074 (15)*
HW42	0.109 (4)	0.195 (2)	0.4781 (9)	0.037 (10)*
HW12	−0.551 (4)	0.168 (2)	0.4714 (11)	0.043 (11)*
HW11	−0.551 (5)	0.118 (3)	0.5214 (12)	0.079 (15)*
HW31	−0.282 (6)	0.057 (3)	0.5893 (17)	0.119*
HW32	−0.195 (6)	0.009 (2)	0.5475 (17)	0.083 (18)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0317 (17)	0.049 (2)	0.0242 (14)	0.0001 (14)	0.0003 (12)	−0.0013 (14)
C2	0.0318 (18)	0.067 (2)	0.0255 (15)	0.0106 (16)	−0.0019 (13)	−0.0162 (16)
C4	0.043 (2)	0.049 (2)	0.0447 (19)	0.0084 (16)	−0.0065 (16)	−0.0268 (17)
C5	0.045 (2)	0.0296 (17)	0.0447 (19)	0.0040 (14)	−0.0066 (15)	−0.0126 (15)
C6	0.079 (3)	0.0198 (17)	0.072 (3)	0.0021 (16)	−0.007 (2)	−0.0094 (18)
C7	0.074 (3)	0.0221 (18)	0.070 (3)	0.0012 (17)	−0.004 (2)	0.0069 (17)
C8	0.044 (2)	0.0230 (16)	0.0478 (19)	−0.0010 (13)	−0.0031 (15)	0.0094 (14)
C9	0.041 (2)	0.0408 (19)	0.0404 (18)	−0.0060 (15)	−0.0033 (15)	0.0234 (15)
C10	0.0336 (18)	0.054 (2)	0.0251 (15)	0.0009 (14)	0.0010 (13)	0.0107 (15)
C11	0.0318 (16)	0.0369 (17)	0.0235 (14)	0.0024 (13)	−0.0001 (12)	0.0001 (13)
C12	0.0309 (16)	0.0223 (14)	0.0283 (15)	−0.0003 (11)	−0.0022 (12)	−0.0038 (12)
C13	0.0319 (16)	0.0208 (14)	0.0283 (14)	−0.0005 (11)	−0.0027 (12)	0.0022 (12)
C14	0.0353 (17)	0.0180 (14)	0.0273 (14)	−0.0034 (11)	0.0054 (13)	−0.0008 (11)
C15	0.0283 (15)	0.0176 (13)	0.0201 (13)	−0.0006 (10)	0.0004 (11)	0.0004 (10)
C16	0.0236 (14)	0.0201 (13)	0.0180 (12)	0.0012 (10)	0.0012 (11)	0.0023 (10)
C17	0.0331 (16)	0.0264 (15)	0.0161 (12)	−0.0042 (12)	−0.0006 (11)	−0.0004 (11)
C18	0.0241 (14)	0.0152 (12)	0.0167 (12)	−0.0037 (10)	0.0017 (10)	0.0019 (10)
C19	0.0234 (14)	0.0178 (13)	0.0218 (13)	−0.0028 (10)	0.0054 (11)	0.0012 (10)
C20	0.0220 (14)	0.0252 (14)	0.0255 (14)	0.0014 (11)	−0.0029 (11)	−0.0002 (11)
C021	0.0296 (15)	0.0219 (14)	0.0188 (13)	−0.0019 (11)	0.0028 (11)	−0.0009 (11)
C21	0.0279 (15)	0.0220 (14)	0.0233 (13)	0.0030 (11)	−0.0051 (11)	0.0010 (11)
C22	0.0233 (14)	0.0196 (13)	0.0203 (13)	0.0002 (10)	−0.0001 (11)	0.0007 (10)
C23	0.0341 (16)	0.0241 (15)	0.0204 (13)	−0.0099 (12)	0.0031 (12)	−0.0014 (11)
C25	0.0248 (14)	0.0187 (13)	0.0213 (13)	0.0027 (10)	0.0006 (11)	0.0001 (11)
N1	0.0286 (13)	0.0241 (12)	0.0212 (11)	0.0011 (10)	−0.0006 (9)	0.0011 (10)
N2	0.0282 (13)	0.0278 (13)	0.0203 (11)	0.0000 (10)	−0.0019 (9)	−0.0015 (10)
O1	0.0729 (17)	0.0249 (11)	0.0264 (10)	−0.0026 (10)	−0.0152 (11)	0.0063 (9)
O2	0.0529 (14)	0.0266 (11)	0.0248 (10)	0.0048 (9)	−0.0025 (10)	−0.0068 (9)
O1W	0.0282 (12)	0.0574 (16)	0.0270 (12)	−0.0047 (11)	0.0014 (10)	0.0052 (11)
O3	0.0640 (17)	0.0305 (12)	0.0454 (13)	−0.0204 (11)	−0.0111 (12)	0.0083 (10)
O2W	0.0487 (16)	0.0325 (14)	0.0457 (14)	−0.0005 (11)	0.0034 (12)	−0.0171 (11)
O4	0.0527 (15)	0.0370 (13)	0.0507 (14)	−0.0078 (11)	−0.0267 (12)	0.0000 (11)
O3W	0.0611 (18)	0.0372 (15)	0.0482 (15)	−0.0090 (12)	−0.0082 (13)	0.0157 (13)
O5	0.0610 (16)	0.0250 (11)	0.0330 (11)	−0.0052 (10)	−0.0117 (10)	0.0037 (9)
O4W	0.0259 (12)	0.0736 (18)	0.0208 (10)	−0.0078 (11)	0.0007 (9)	0.0006 (11)
O6	0.0551 (15)	0.0235 (11)	0.0328 (11)	−0.0068 (9)	−0.0142 (10)	−0.0010 (9)
O7	0.0495 (14)	0.0329 (12)	0.0184 (9)	0.0085 (10)	0.0031 (9)	0.0025 (8)
O8	0.0507 (14)	0.0341 (12)	0.0267 (11)	0.0174 (10)	0.0063 (10)	0.0014 (9)
Zn1	0.0328 (2)	0.0265 (2)	0.0280 (2)	0.00085 (14)	−0.00117 (14)	0.00085 (14)

Geometric parameters (Å, º) top

C1—N2	1.333 (3)	C18—C21	1.499 (4)
C1—C2	1.410 (4)	C18—C22	1.543 (3)
C1—H1	0.9300	C18—H18	0.9800
C2—C4	1.346 (5)	C19—C20	1.498 (4)
C2—H2	0.9300	C19—C25	1.545 (4)
C4—C5	1.403 (5)	C19—H19	0.9800
C4—H4	0.9300	C20—C21	1.325 (4)
C5—C12	1.420 (4)	C20—H20	0.9300
C5—C6	1.428 (5)	C021—O8	1.248 (3)
C6—C7	1.333 (6)	C021—O7	1.254 (3)
C6—H6	0.9300	C021—C25	1.539 (3)
C7—C8	1.434 (5)	C21—H21	0.9300
C7—H7	0.9300	C22—C23	1.526 (3)
C8—C9	1.402 (4)	C22—C25	1.564 (3)
C8—C13	1.419 (4)	C22—H22	0.9800
C9—C10	1.343 (4)	C23—O5	1.200 (3)
C9—H9	0.9300	C23—O6	1.309 (3)
C10—C11	1.403 (4)	C25—H25	0.9800
C10—H10	0.9300	N1—Zn1	2.073 (2)
C11—N1	1.333 (3)	N2—Zn1	2.087 (2)
C11—H11	0.9300	O1W—Zn1	2.074 (2)
C12—N2	1.344 (3)	O1W—HW12	0.816 (17)
C12—C13	1.442 (4)	O1W—HW11	0.826 (18)
C13—N1	1.345 (3)	O3—H3	0.8200
C14—O4	1.198 (3)	O2W—Zn1	2.055 (2)
C14—O3	1.300 (3)	O2W—HW22	0.799 (17)
C14—C15	1.528 (4)	O2W—HW21	0.809 (17)
C15—C16	1.561 (3)	O3W—Zn1	2.067 (2)
C15—C19	1.567 (3)	O3W—HW31	0.80 (4)
C15—H15	0.9800	O3W—HW32	0.784 (18)
C16—C17	1.531 (3)	O4W—Zn1	2.041 (2)
C16—C18	1.541 (3)	O4W—HW41	0.845 (18)
C16—H16	0.9800	O4W—HW42	0.811 (17)
C17—O1	1.240 (3)	O6—H6A	0.8200
C17—O2	1.279 (3)

N2—C1—C2	121.9 (3)	C20—C19—H19	110.4
N2—C1—H1	119.1	C25—C19—H19	110.4
C2—C1—H1	119.1	C15—C19—H19	110.4
C4—C2—C1	120.0 (3)	C21—C20—C19	114.3 (2)
C4—C2—H2	120.0	C21—C20—H20	122.9
C1—C2—H2	120.0	C19—C20—H20	122.9
C2—C4—C5	120.3 (3)	O8—C021—O7	124.5 (2)
C2—C4—H4	119.8	O8—C021—C25	119.8 (2)
C5—C4—H4	119.8	O7—C021—C25	115.7 (2)
C4—C5—C12	115.9 (3)	C20—C21—C18	113.9 (2)
C4—C5—C6	124.4 (3)	C20—C21—H21	123.0
C12—C5—C6	119.7 (3)	C18—C21—H21	123.0
C7—C6—C5	121.4 (3)	C23—C22—C18	113.0 (2)
C7—C6—H6	119.3	C23—C22—C25	115.1 (2)
C5—C6—H6	119.3	C18—C22—C25	109.2 (2)
C6—C7—C8	121.7 (3)	C23—C22—H22	106.3
C6—C7—H7	119.2	C18—C22—H22	106.3
C8—C7—H7	119.2	C25—C22—H22	106.3
C9—C8—C13	116.4 (3)	O5—C23—O6	124.9 (3)
C9—C8—C7	124.9 (3)	O5—C23—C22	125.2 (2)
C13—C8—C7	118.8 (3)	O6—C23—C22	109.7 (2)
C10—C9—C8	120.3 (3)	C021—C25—C19	110.9 (2)
C10—C9—H9	119.8	C021—C25—C22	115.2 (2)
C8—C9—H9	119.8	C19—C25—C22	108.0 (2)
C9—C10—C11	120.1 (3)	C021—C25—H25	107.5
C9—C10—H10	119.9	C19—C25—H25	107.5
C11—C10—H10	119.9	C22—C25—H25	107.5
N1—C11—C10	121.6 (3)	C11—N1—C13	118.6 (2)
N1—C11—H11	119.2	C11—N1—Zn1	128.64 (19)
C10—C11—H11	119.2	C13—N1—Zn1	112.79 (17)
N2—C12—C5	124.0 (3)	C1—N2—C12	117.8 (3)
N2—C12—C13	117.4 (2)	C1—N2—Zn1	129.8 (2)
C5—C12—C13	118.6 (3)	C12—N2—Zn1	112.28 (17)
N1—C13—C8	123.0 (3)	Zn1—O1W—HW12	115 (2)
N1—C13—C12	117.2 (2)	Zn1—O1W—HW11	122 (3)
C8—C13—C12	119.8 (3)	HW12—O1W—HW11	109 (3)
O4—C14—O3	123.8 (3)	C14—O3—H3	109.5
O4—C14—C15	124.2 (2)	Zn1—O2W—HW22	124 (3)
O3—C14—C15	111.9 (2)	Zn1—O2W—HW21	124 (3)
C14—C15—C16	114.5 (2)	HW22—O2W—HW21	112 (3)
C14—C15—C19	108.6 (2)	Zn1—O3W—HW31	122 (4)
C16—C15—C19	107.85 (19)	Zn1—O3W—HW32	105 (3)
C14—C15—H15	108.6	HW31—O3W—HW32	117 (3)
C16—C15—H15	108.6	Zn1—O4W—HW41	127 (3)
C19—C15—H15	108.6	Zn1—O4W—HW42	121 (2)
C17—C16—C18	113.1 (2)	HW41—O4W—HW42	106 (3)
C17—C16—C15	113.9 (2)	C23—O6—H6A	109.5
C18—C16—C15	109.2 (2)	O4W—Zn1—O2W	84.42 (10)
C17—C16—H16	106.7	O4W—Zn1—O3W	90.23 (10)
C18—C16—H16	106.7	O2W—Zn1—O3W	91.20 (12)
C15—C16—H16	106.7	O4W—Zn1—N1	92.69 (9)
O1—C17—O2	123.3 (2)	O2W—Zn1—N1	93.26 (10)
O1—C17—C16	120.1 (2)	O3W—Zn1—N1	174.89 (11)
O2—C17—C16	116.4 (2)	O4W—Zn1—O1W	173.09 (10)
C21—C18—C16	109.5 (2)	O2W—Zn1—O1W	90.46 (10)
C21—C18—C22	108.7 (2)	O3W—Zn1—O1W	85.22 (10)
C16—C18—C22	107.0 (2)	N1—Zn1—O1W	92.24 (9)
C21—C18—H18	110.5	O4W—Zn1—N2	90.00 (9)
C16—C18—H18	110.5	O2W—Zn1—N2	171.08 (10)
C22—C18—H18	110.5	O3W—Zn1—N2	95.79 (11)
C20—C19—C25	109.3 (2)	N1—Zn1—N2	80.02 (9)
C20—C19—C15	107.7 (2)	O1W—Zn1—N2	95.62 (9)
C25—C19—C15	108.5 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O8ⁱ	0.82	1.88	2.674 (3)	163
O6—H6A···O2ⁱⁱ	0.82	1.84	2.583 (3)	151
O2W—HW22···O2ⁱⁱⁱ	0.80 (2)	2.06 (2)	2.818 (3)	158 (4)
O4W—HW41···O1	0.85 (2)	1.86 (2)	2.705 (3)	174 (4)
O2W—HW21···O8^iv	0.81 (2)	2.12 (2)	2.904 (3)	163 (4)
O4W—HW42···O7^iv	0.81 (2)	1.88 (2)	2.686 (3)	177 (3)
O1W—HW12···O7^v	0.82 (2)	2.09 (2)	2.884 (3)	165 (3)
O1W—HW11···O2^vi	0.83 (2)	2.13 (2)	2.923 (3)	160 (4)
O3W—HW31···O2^vi	0.80 (4)	2.57 (4)	3.233 (4)	142 (5)

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

Experimental details

Crystal data
Chemical formula	[Zn(C₁₂H₈N₂)(H₂O)₄](C₁₂H₁₀O₈)
M_r	599.84
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	7.4550 (2), 13.5991 (4), 22.9833 (7)
β (°)	91.555 (1)
V (Å³)	2329.22 (12)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.13
Crystal size (mm)	0.33 × 0.22 × 0.19

Data collection
Diffractometer	Bruker APEX CCD area-detector diffractometer
Absorption correction	Multi-scan (SAINT; Bruker, 1998)
T_min, T_max	0.687, 0.805
No. of measured, independent and observed [I > 2σ(I)] reflections	14301, 5626, 3854
R_int	0.048
(sin θ/λ)_max (Å⁻¹)	0.666

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.122, 0.96
No. of reflections	5626
No. of parameters	382
No. of restraints	12
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.50, −0.59

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O8ⁱ	0.82	1.88	2.674 (3)	163.2
O6—H6A···O2ⁱⁱ	0.82	1.84	2.583 (3)	150.9
O2W—HW22···O2ⁱⁱⁱ	0.799 (17)	2.06 (2)	2.818 (3)	158 (4)
O4W—HW41···O1	0.845 (18)	1.86 (2)	2.705 (3)	174 (4)
O2W—HW21···O8^iv	0.809 (17)	2.121 (18)	2.904 (3)	163 (4)
O4W—HW42···O7^iv	0.811 (17)	1.876 (17)	2.686 (3)	177 (3)
O1W—HW12···O7^v	0.816 (17)	2.09 (2)	2.884 (3)	165 (3)
O1W—HW11···O2^vi	0.826 (18)	2.13 (2)	2.923 (3)	160 (4)
O3W—HW31···O2^vi	0.80 (4)	2.57 (4)	3.233 (4)	142 (5)

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

Acknowledgements

The authors thank Beihua University for supporting this work.

References

Bruker (1998). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Hu, T. (2008). Acta Cryst. E64, o1021. Web of Science CSD CrossRef IUCr Journals Google Scholar
Ma, J.-F., Yang, J., Zheng, G.-L., Li, L. & Liu, J.-F. (2003). Inorg. Chem. 42, 7531–7534. Web of Science CSD CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 64| Part 9| September 2008| Page m1158

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

Tetra­aqua­(1,10-phenanthroline)zinc(II) 3,6-di­carb­oxy­bi­cyclo­[2.2.2]oct-7-ene-2,5-di­carboxyl­ate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

metal-organic compounds

Tetraaqua(1,10-phenanthroline)zinc(II) 3,6-dicarboxybicyclo[2.2.2]oct-7-ene-2,5-dicarboxylate