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

Liu, Y.-Y.; Wang, T.-H.; Wang, Z.-H.; Zhuo, Y.-J.; Li, X.-Q.

doi:10.1107/S1600536809028190

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 8| August 2009| Page m978

doi:10.1107/S1600536809028190

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

Yun-Yu Liu,^a ^* Tian-Hui Wang,^b Zhi-Hao Wang,^c Yu-Jiang Zhuo ^a and Xing-Qi Li ^a

^aDepartment of Chemistry, Northeast Normal University, Changchun 130024, People's Republic of China, ^bGroup of Chemistry, High School Attached to Northeast Normal University, Changchun 130024, People's Republic of China, and ^cEmergency Department, the First Clinical Hospital Affiliated to Jilin University, Changchun 130021, People's Republic of China
^*Correspondence e-mail: yunyuliu888@yahoo.com.cn

(Received 2 July 2009; accepted 17 July 2009; online 22 July 2009)

In the title compound, [Ni(C₁₂H₈N₂)(H₂O)₄](C₁₂H₁₀O₈), the Ni^II ion is six-coordinated by two N atoms from one phenanthroline ligand and by the O atoms of four water molecules in a distorted octahedral geometry. In the crystal, intermolecular O—H⋯O hydrogen bonds form an extensive three-dimensional network, which consolidates the crystal packing.

Related literature

For a related structure, see Liu et al. (2008 ).

Experimental

Crystal data

[Ni(C₁₂H₈N₂)(H₂O)₄](C₁₂H₁₀O₈)
M_r = 593.18
Monoclinic, P 2₁ /c
a = 7.446 (5) Å
b = 13.583 (6) Å
c = 22.982 (9) Å
β = 91.549 (7)°
V = 2323.5 (18) Å³
Z = 4
Mo Kα radiation
μ = 0.91 mm⁻¹
T = 293 K
0.30 × 0.28 × 0.17 mm

Data collection

Bruker APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick 1996 ) T_min = 0.756, T_max = 0.855
14211 measured reflections
5636 independent reflections
4321 reflections with I > 2σ(I)
R_int = 0.032

Refinement

R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.133
S = 1.10
5636 reflections
382 parameters
12 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.46 e Å⁻³
Δρ_min = −0.47 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O7—H7⋯O3ⁱ	0.82	1.83	2.576 (3)	151
O1—H1⋯O6ⁱⁱ	0.82	1.88	2.670 (3)	163
O1W—HW11⋯O4	0.828 (16)	1.897 (18)	2.716 (3)	170 (3)
O1W—HW12⋯O5ⁱⁱⁱ	0.859 (17)	1.828 (18)	2.682 (3)	173 (3)
O4W—HW41⋯O5^iv	0.845 (18)	2.07 (3)	2.879 (3)	161 (4)
O4W—HW42⋯O3^v	0.849 (18)	2.16 (2)	2.926 (3)	150 (4)
O3W—HW31⋯O3^vi	0.863 (17)	1.958 (17)	2.814 (3)	171 (3)
O3W—HW32⋯O6ⁱⁱⁱ	0.850 (17)	2.060 (19)	2.893 (3)	166 (4)
O2W—HW21⋯O3^v	0.844 (18)	2.47 (2)	3.244 (4)	153 (4)
O2W—HW22⋯O2	0.853 (18)	2.01 (2)	2.806 (3)	154 (4)
Symmetry codes: (i) $[-x+2, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (iv) $[x-1, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (v) x-1, y, z; (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-Plus (Sheldrick, 2008); software used to prepare material for publication: SHELXTL-Plus.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809028190/cv2585sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809028190/cv2585Isup2.hkl

checkCIF report

Comment top

Coordination polymers based on poly(carboxylic acids) have been investigated in the area of solid state and material science (Liu et al., 2008). We 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 complex, [Ni(phen)(H₂O)₄][(H₂L)], which is reported here.

In the title compound (I) (Fig. 1), each Ni^II ion 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 (Table 1).

Related literature top

For a related structure, see Liu et al. (2008).

Experimental top

A mixture of H₄L (0.5 mmol), phen (0.5 mmol), NaOH (1 mmol) and NiCl₂^.2H₂O (0.5 mmol) was suspended in 12 ml of deionized water and sealed in a 20-ml Teflon-lined autoclave. Upon heating at 100°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-Plus (Sheldrick, 2008); software used to prepare material for publication: SHELXTL-Plus (Sheldrick, 2008).

Figures top

Fig. 1. The structure of (I), showing the atomic numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.

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

Crystal data top

[Ni(C₁₂H₈N₂)(H₂O)₄](C₁₂H₁₀O₈)	F(000) = 1232
M_r = 593.18	D_x = 1.696 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71069 Å
Hall symbol: -P 2ybc	Cell parameters from 5636 reflections
a = 7.446 (5) Å	θ = 3.0–28.3°
b = 13.583 (6) Å	µ = 0.91 mm⁻¹
c = 22.982 (9) Å	T = 293 K
β = 91.549 (7)°	Block, green
V = 2323.5 (18) Å³	0.30 × 0.28 × 0.17 mm
Z = 4

Data collection top

Bruker APEX CCD area-detector diffractometer	5636 independent reflections
Radiation source: fine-focus sealed tube	4321 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.032
ϕ and ω scans	θ_max = 28.3°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick 1996)	h = −9→8
T_min = 0.756, T_max = 0.855	k = −14→18
14211 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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.133	H atoms treated by a mixture of independent and constrained refinement
S = 1.10	w = 1/[σ²(F_o²) + (0.0737P)² + 0.0226P] where P = (F_o² + 2F_c²)/3
5636 reflections	(Δ/σ)_max = 0.001
382 parameters	Δρ_max = 0.46 e Å⁻³
12 restraints	Δρ_min = −0.47 e Å⁻³

Crystal data top

[Ni(C₁₂H₈N₂)(H₂O)₄](C₁₂H₁₀O₈)	V = 2323.5 (18) Å³
M_r = 593.18	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 7.446 (5) Å	µ = 0.91 mm⁻¹
b = 13.583 (6) Å	T = 293 K
c = 22.982 (9) Å	0.30 × 0.28 × 0.17 mm
β = 91.549 (7)°

Data collection top

Bruker APEX CCD area-detector diffractometer	5636 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick 1996)	4321 reflections with I > 2σ(I)
T_min = 0.756, T_max = 0.855	R_int = 0.032
14211 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	12 restraints
wR(F²) = 0.133	H atoms treated by a mixture of independent and constrained refinement
S = 1.10	Δρ_max = 0.46 e Å⁻³
5636 reflections	Δρ_min = −0.47 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
Ni1	0.27952 (4)	0.16490 (2)	−0.000262 (12)	0.02453 (12)
O3	0.8856 (3)	0.08862 (13)	0.10988 (7)	0.0376 (5)
O8	0.8695 (3)	0.49129 (14)	0.26041 (8)	0.0426 (5)
O5	0.7531 (3)	0.27133 (14)	0.41536 (7)	0.0373 (5)
O6	0.5963 (3)	0.36870 (14)	0.35586 (8)	0.0399 (5)
O7	0.9935 (3)	0.42968 (14)	0.34205 (8)	0.0401 (5)
H7	1.0005	0.4878	0.3514	0.060*
O4	0.7696 (3)	0.23715 (14)	0.09583 (8)	0.0441 (5)
O1	0.6022 (3)	−0.02746 (14)	0.22071 (9)	0.0508 (6)
H1	0.5256	−0.0589	0.2024	0.076*
C14	0.6501 (3)	0.19162 (17)	0.27782 (10)	0.0236 (5)
H14	0.5749	0.1518	0.3031	0.028*
O4W	0.0076 (3)	0.13193 (18)	−0.00734 (9)	0.0413 (5)
C18	0.8609 (3)	0.19220 (16)	0.19325 (9)	0.0232 (5)
H18	0.9876	0.1783	0.2026	0.028*
C23	0.7086 (3)	0.30189 (18)	0.36551 (10)	0.0261 (5)
O2	0.5126 (3)	0.09191 (15)	0.16145 (9)	0.0502 (6)
C5	0.2366 (5)	0.5506 (2)	0.02235 (17)	0.0571 (9)
H5	0.2348	0.6111	0.0413	0.069*
O3W	0.3341 (3)	0.06193 (16)	−0.06306 (9)	0.0455 (5)
C17	0.8282 (3)	0.30067 (16)	0.20957 (9)	0.0215 (5)
H17	0.8902	0.3447	0.1829	0.026*
N2	0.2543 (3)	0.27843 (15)	−0.06039 (8)	0.0270 (4)
C13	0.7483 (3)	0.12471 (17)	0.23318 (10)	0.0243 (5)
H13	0.8303	0.0807	0.2547	0.029*
C19	0.5369 (3)	0.26471 (17)	0.24367 (10)	0.0268 (5)
H19	0.4132	0.2699	0.2472	0.032*
N1	0.2510 (3)	0.28369 (16)	0.05628 (8)	0.0284 (5)
O1W	0.5511 (3)	0.17925 (18)	0.00568 (9)	0.0436 (5)
C16	0.9011 (3)	0.31475 (16)	0.27256 (10)	0.0232 (5)
H16	1.0243	0.2893	0.2733	0.028*
C12	0.2464 (3)	0.37093 (19)	0.02772 (11)	0.0292 (5)
C20	0.6303 (3)	0.32107 (17)	0.20793 (10)	0.0268 (5)
H20	0.5774	0.3688	0.1841	0.032*
C22	0.8323 (4)	0.17204 (18)	0.12814 (10)	0.0270 (5)
C15	0.7941 (3)	0.24788 (16)	0.31430 (9)	0.0236 (5)
H15	0.8781	0.1991	0.3307	0.028*
C4	0.2392 (4)	0.4628 (2)	0.05558 (13)	0.0421 (7)
C24	0.9147 (4)	0.42251 (18)	0.29031 (10)	0.0286 (5)
C21	0.6078 (4)	0.06232 (17)	0.20067 (11)	0.0291 (5)
O2W	0.2891 (4)	0.05750 (18)	0.06329 (10)	0.0535 (6)
C11	0.2481 (4)	0.36777 (18)	−0.03492 (11)	0.0295 (5)
C9	0.2349 (4)	0.3574 (2)	−0.15295 (12)	0.0400 (7)
H9	0.2291	0.3514	−0.1933	0.048*
C2	0.2350 (4)	0.3740 (3)	0.14546 (12)	0.0435 (7)
H2	0.2317	0.3726	0.1859	0.052*
C1	0.2445 (4)	0.2857 (2)	0.11400 (11)	0.0377 (6)
H1A	0.2464	0.2264	0.1343	0.045*
C8	0.2324 (4)	0.4475 (2)	−0.12781 (13)	0.0440 (7)
H8	0.2249	0.5037	−0.1509	0.053*
C7	0.2409 (4)	0.4560 (2)	−0.06704 (13)	0.0410 (7)
C3	0.2306 (4)	0.4607 (2)	0.11710 (14)	0.0491 (8)
H3	0.2219	0.5192	0.1379	0.059*
C10	0.2463 (4)	0.2735 (2)	−0.11797 (11)	0.0330 (6)
H10	0.2484	0.2120	−0.1357	0.040*
C6	0.2366 (5)	0.5477 (2)	−0.03657 (17)	0.0603 (10)
H6	0.2338	0.6063	−0.0575	0.072*
HW11	0.608 (4)	0.203 (2)	0.0338 (8)	0.035 (8)*
HW12	0.618 (4)	0.190 (2)	−0.0236 (9)	0.063 (11)*
HW41	−0.045 (6)	0.163 (3)	−0.0348 (13)	0.12 (2)*
HW42	−0.063 (5)	0.128 (3)	0.0208 (12)	0.086 (14)*
HW31	0.273 (4)	0.017 (2)	−0.0808 (14)	0.068 (12)*
HW32	0.418 (4)	0.072 (3)	−0.0868 (14)	0.081*
HW21	0.191 (3)	0.045 (3)	0.0794 (16)	0.081*
HW22	0.370 (4)	0.051 (3)	0.0900 (14)	0.096 (16)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ni1	0.02791 (19)	0.02203 (18)	0.02354 (18)	0.00082 (12)	−0.00149 (13)	0.00083 (12)
O3	0.0548 (13)	0.0316 (10)	0.0263 (9)	0.0051 (9)	−0.0030 (9)	−0.0066 (8)
O8	0.0632 (14)	0.0291 (10)	0.0349 (10)	−0.0053 (9)	−0.0107 (9)	0.0035 (8)
O5	0.0533 (13)	0.0376 (11)	0.0210 (8)	0.0078 (9)	0.0010 (8)	0.0027 (8)
O6	0.0540 (13)	0.0357 (11)	0.0300 (10)	0.0183 (9)	0.0041 (9)	0.0010 (8)
O7	0.0578 (13)	0.0266 (9)	0.0351 (10)	−0.0064 (9)	−0.0133 (9)	−0.0012 (8)
O4	0.0745 (16)	0.0287 (10)	0.0282 (9)	−0.0031 (9)	−0.0150 (9)	0.0067 (8)
O1	0.0688 (16)	0.0326 (11)	0.0503 (12)	−0.0225 (10)	−0.0133 (11)	0.0088 (9)
C14	0.0260 (12)	0.0218 (11)	0.0231 (11)	−0.0028 (9)	0.0042 (9)	0.0010 (9)
O4W	0.0308 (11)	0.0613 (14)	0.0319 (11)	−0.0050 (10)	0.0007 (9)	0.0032 (10)
C18	0.0272 (12)	0.0215 (11)	0.0210 (11)	0.0011 (9)	−0.0003 (9)	0.0019 (9)
C23	0.0334 (14)	0.0245 (12)	0.0206 (11)	−0.0027 (10)	0.0019 (10)	−0.0002 (9)
O2	0.0563 (14)	0.0408 (12)	0.0521 (13)	−0.0081 (10)	−0.0261 (11)	0.0006 (10)
C5	0.072 (2)	0.0250 (16)	0.074 (2)	0.0029 (14)	−0.0051 (19)	−0.0120 (16)
O3W	0.0501 (14)	0.0389 (12)	0.0476 (12)	−0.0010 (10)	0.0042 (10)	−0.0199 (10)
C17	0.0268 (12)	0.0186 (11)	0.0192 (10)	−0.0039 (9)	0.0000 (9)	0.0021 (9)
N2	0.0311 (11)	0.0262 (11)	0.0236 (10)	0.0009 (8)	−0.0011 (8)	0.0011 (8)
C13	0.0299 (13)	0.0205 (11)	0.0226 (11)	−0.0002 (9)	0.0005 (10)	0.0006 (9)
C19	0.0237 (12)	0.0268 (12)	0.0297 (12)	0.0013 (9)	−0.0028 (10)	−0.0004 (10)
N1	0.0308 (12)	0.0314 (12)	0.0229 (10)	0.0003 (9)	−0.0014 (8)	−0.0016 (9)
O1W	0.0281 (11)	0.0796 (17)	0.0229 (10)	−0.0082 (10)	−0.0016 (8)	−0.0010 (10)
C16	0.0246 (12)	0.0229 (12)	0.0219 (11)	−0.0008 (9)	−0.0010 (9)	−0.0004 (9)
C12	0.0309 (14)	0.0259 (12)	0.0307 (13)	0.0002 (10)	−0.0022 (10)	−0.0028 (11)
C20	0.0303 (13)	0.0246 (12)	0.0252 (12)	0.0038 (10)	−0.0053 (10)	0.0012 (9)
C22	0.0356 (14)	0.0270 (13)	0.0182 (11)	−0.0044 (10)	0.0003 (10)	−0.0001 (9)
C15	0.0276 (12)	0.0202 (11)	0.0228 (11)	0.0023 (9)	−0.0018 (9)	0.0005 (9)
C4	0.0464 (18)	0.0324 (15)	0.0469 (17)	0.0038 (12)	−0.0076 (13)	−0.0126 (13)
C24	0.0358 (14)	0.0268 (13)	0.0231 (12)	−0.0106 (10)	0.0023 (10)	−0.0009 (10)
C21	0.0374 (15)	0.0211 (12)	0.0289 (13)	−0.0029 (10)	0.0038 (11)	−0.0007 (10)
O2W	0.0576 (15)	0.0490 (13)	0.0531 (14)	−0.0126 (12)	−0.0113 (12)	0.0219 (11)
C11	0.0322 (14)	0.0238 (12)	0.0322 (13)	0.0004 (10)	−0.0035 (11)	0.0015 (10)
C9	0.0369 (16)	0.0559 (19)	0.0270 (13)	0.0007 (13)	−0.0006 (12)	0.0105 (13)
C2	0.0333 (16)	0.069 (2)	0.0281 (14)	0.0083 (14)	−0.0010 (11)	−0.0159 (14)
C1	0.0351 (15)	0.0514 (18)	0.0266 (13)	0.0016 (13)	0.0000 (11)	−0.0016 (12)
C8	0.0439 (17)	0.0444 (18)	0.0434 (16)	−0.0051 (13)	−0.0035 (13)	0.0230 (14)
C7	0.0465 (18)	0.0266 (14)	0.0497 (17)	−0.0016 (12)	−0.0031 (14)	0.0085 (12)
C3	0.0481 (19)	0.052 (2)	0.0463 (17)	0.0107 (14)	−0.0071 (14)	−0.0260 (16)
C10	0.0334 (14)	0.0390 (15)	0.0264 (12)	0.0019 (11)	−0.0015 (11)	0.0001 (11)
C6	0.082 (3)	0.0236 (15)	0.075 (2)	0.0015 (15)	−0.007 (2)	0.0080 (16)

Geometric parameters (Å, º) top

Ni1—O1W	2.033 (2)	N2—C10	1.325 (3)
Ni1—O3W	2.058 (2)	N2—C11	1.349 (3)
Ni1—O2W	2.064 (2)	C13—C21	1.526 (3)
Ni1—N2	2.076 (2)	C13—H13	0.9800
Ni1—O4W	2.076 (2)	C19—C20	1.332 (3)
Ni1—N1	2.086 (2)	C19—H19	0.9300
O3—C22	1.275 (3)	N1—C1	1.329 (3)
O8—C24	1.203 (3)	N1—C12	1.355 (3)
O5—C23	1.255 (3)	O1W—HW11	0.828 (16)
O6—C23	1.250 (3)	O1W—HW12	0.859 (17)
O7—C24	1.315 (3)	C16—C24	1.522 (3)
O7—H7	0.8200	C16—C15	1.556 (3)
O4—C22	1.238 (3)	C16—H16	0.9800
O1—C21	1.305 (3)	C12—C4	1.404 (4)
O1—H1	0.8200	C12—C11	1.441 (4)
C14—C19	1.509 (3)	C20—H20	0.9300
C14—C15	1.545 (3)	C15—H15	0.9800
C14—C13	1.566 (3)	C4—C3	1.417 (4)
C14—H14	0.9800	O2W—HW21	0.844 (18)
O4W—HW41	0.845 (18)	O2W—HW22	0.853 (18)
O4W—HW42	0.849 (18)	C11—C7	1.408 (4)
C18—C22	1.530 (3)	C9—C8	1.353 (4)
C18—C17	1.541 (3)	C9—C10	1.396 (4)
C18—C13	1.558 (3)	C9—H9	0.9300
C18—H18	0.9800	C2—C3	1.346 (5)
C23—C15	1.539 (3)	C2—C1	1.403 (4)
O2—C21	1.201 (3)	C2—H2	0.9300
C5—C6	1.355 (6)	C1—H1A	0.9300
C5—C4	1.416 (4)	C8—C7	1.401 (4)
C5—H5	0.9300	C8—H8	0.9300
O3W—HW31	0.863 (17)	C7—C6	1.430 (4)
O3W—HW32	0.850 (17)	C3—H3	0.9300
C17—C20	1.499 (3)	C10—H10	0.9300
C17—C16	1.544 (3)	C6—H6	0.9300
C17—H17	0.9800

O1W—Ni1—O3W	84.11 (9)	Ni1—O1W—HW12	124 (2)
O1W—Ni1—O2W	90.27 (10)	HW11—O1W—HW12	105 (2)
O3W—Ni1—O2W	90.69 (11)	C24—C16—C17	112.92 (19)
O1W—Ni1—N2	92.61 (9)	C24—C16—C15	115.33 (19)
O3W—Ni1—N2	93.10 (9)	C17—C16—C15	109.46 (19)
O2W—Ni1—N2	175.45 (10)	C24—C16—H16	106.1
O1W—Ni1—O4W	173.00 (9)	C17—C16—H16	106.1
O3W—Ni1—O4W	90.51 (9)	C15—C16—H16	106.1
O2W—Ni1—O4W	85.31 (10)	N1—C12—C4	123.9 (2)
N2—Ni1—O4W	92.15 (9)	N1—C12—C11	117.2 (2)
O1W—Ni1—N1	90.11 (9)	C4—C12—C11	118.9 (2)
O3W—Ni1—N1	171.03 (9)	C19—C20—C17	114.0 (2)
O2W—Ni1—N1	96.20 (10)	C19—C20—H20	123.0
N2—Ni1—N1	80.28 (9)	C17—C20—H20	123.0
O4W—Ni1—N1	95.75 (9)	O4—C22—O3	123.6 (2)
C24—O7—H7	109.5	O4—C22—C18	119.9 (2)
C21—O1—H1	109.5	O3—C22—C18	116.4 (2)
C19—C14—C15	109.06 (19)	C23—C15—C14	110.8 (2)
C19—C14—C13	107.77 (18)	C23—C15—C16	114.98 (19)
C15—C14—C13	108.25 (19)	C14—C15—C16	108.26 (18)
C19—C14—H14	110.6	C23—C15—H15	107.5
C15—C14—H14	110.6	C14—C15—H15	107.5
C13—C14—H14	110.6	C16—C15—H15	107.5
Ni1—O4W—HW41	112 (3)	C12—C4—C5	120.2 (3)
Ni1—O4W—HW42	125 (3)	C12—C4—C3	116.1 (3)
HW41—O4W—HW42	108 (3)	C5—C4—C3	123.7 (3)
C22—C18—C17	112.97 (19)	O8—C24—O7	124.8 (2)
C22—C18—C13	114.05 (19)	O8—C24—C16	125.3 (2)
C17—C18—C13	109.14 (18)	O7—C24—C16	109.8 (2)
C22—C18—H18	106.7	O2—C21—O1	123.7 (2)
C17—C18—H18	106.7	O2—C21—C13	124.4 (2)
C13—C18—H18	106.7	O1—C21—C13	112.0 (2)
O6—C23—O5	124.1 (2)	Ni1—O2W—HW21	116 (3)
O6—C23—C15	119.9 (2)	Ni1—O2W—HW22	127 (3)
O5—C23—C15	115.8 (2)	HW21—O2W—HW22	105 (2)
C6—C5—C4	121.0 (3)	N2—C11—C7	122.7 (2)
C6—C5—H5	119.5	N2—C11—C12	117.5 (2)
C4—C5—H5	119.5	C7—C11—C12	119.8 (2)
Ni1—O3W—HW31	135 (2)	C8—C9—C10	119.6 (3)
Ni1—O3W—HW32	120 (2)	C8—C9—H9	120.2
HW31—O3W—HW32	102 (2)	C10—C9—H9	120.2
C20—C17—C18	109.41 (19)	C3—C2—C1	120.0 (3)
C20—C17—C16	108.71 (18)	C3—C2—H2	120.0
C18—C17—C16	107.02 (18)	C1—C2—H2	120.0
C20—C17—H17	110.5	N1—C1—C2	122.4 (3)
C18—C17—H17	110.5	N1—C1—H1A	118.8
C16—C17—H17	110.5	C2—C1—H1A	118.8
C10—N2—C11	118.6 (2)	C9—C8—C7	120.0 (3)
C10—N2—Ni1	128.91 (18)	C9—C8—H8	120.0
C11—N2—Ni1	112.52 (16)	C7—C8—H8	120.0
C21—C13—C18	114.28 (19)	C8—C7—C11	116.9 (3)
C21—C13—C14	108.5 (2)	C8—C7—C6	124.0 (3)
C18—C13—C14	108.22 (18)	C11—C7—C6	119.1 (3)
C21—C13—H13	108.6	C2—C3—C4	119.9 (3)
C18—C13—H13	108.6	C2—C3—H3	120.0
C14—C13—H13	108.6	C4—C3—H3	120.0
C20—C19—C14	113.9 (2)	N2—C10—C9	122.3 (3)
C20—C19—H19	123.0	N2—C10—H10	118.9
C14—C19—H19	123.0	C9—C10—H10	118.9
C1—N1—C12	117.7 (2)	C5—C6—C7	121.0 (3)
C1—N1—Ni1	130.1 (2)	C5—C6—H6	119.5
C12—N1—Ni1	112.11 (16)	C7—C6—H6	119.5
Ni1—O1W—HW11	125.5 (19)

C22—C18—C17—C20	74.5 (2)	O6—C23—C15—C16	60.0 (3)
C13—C18—C17—C20	−53.5 (2)	O5—C23—C15—C16	−123.0 (2)
C22—C18—C17—C16	−167.88 (19)	C19—C14—C15—C23	72.3 (2)
C13—C18—C17—C16	64.1 (2)	C13—C14—C15—C23	−170.72 (18)
O1W—Ni1—N2—C10	94.5 (2)	C19—C14—C15—C16	−54.7 (2)
O3W—Ni1—N2—C10	10.3 (2)	C13—C14—C15—C16	62.3 (2)
O2W—Ni1—N2—C10	−136.3 (11)	C24—C16—C15—C23	3.4 (3)
O4W—Ni1—N2—C10	−80.4 (2)	C17—C16—C15—C23	−125.2 (2)
N1—Ni1—N2—C10	−175.8 (2)	C24—C16—C15—C14	127.9 (2)
O1W—Ni1—N2—C11	−84.57 (18)	C17—C16—C15—C14	−0.7 (3)
O3W—Ni1—N2—C11	−168.81 (18)	N1—C12—C4—C5	179.4 (3)
O2W—Ni1—N2—C11	44.7 (12)	C11—C12—C4—C5	−1.0 (4)
O4W—Ni1—N2—C11	100.56 (18)	N1—C12—C4—C3	−2.1 (4)
N1—Ni1—N2—C11	5.09 (17)	C11—C12—C4—C3	177.5 (3)
C22—C18—C13—C21	−9.4 (3)	C6—C5—C4—C12	1.6 (6)
C17—C18—C13—C21	118.0 (2)	C6—C5—C4—C3	−176.8 (4)
C22—C18—C13—C14	−130.4 (2)	C17—C16—C24—O8	2.3 (4)
C17—C18—C13—C14	−3.0 (3)	C15—C16—C24—O8	−124.5 (3)
C19—C14—C13—C21	−67.1 (2)	C17—C16—C24—O7	−173.9 (2)
C15—C14—C13—C21	175.12 (19)	C15—C16—C24—O7	59.2 (3)
C19—C14—C13—C18	57.4 (2)	C18—C13—C21—O2	−42.5 (4)
C15—C14—C13—C18	−60.4 (2)	C14—C13—C21—O2	78.3 (3)
C15—C14—C19—C20	58.8 (3)	C18—C13—C21—O1	137.8 (2)
C13—C14—C19—C20	−58.5 (3)	C14—C13—C21—O1	−101.3 (2)
O1W—Ni1—N1—C1	−89.4 (2)	C10—N2—C11—C7	−2.6 (4)
O3W—Ni1—N1—C1	−139.2 (5)	Ni1—N2—C11—C7	176.5 (2)
O2W—Ni1—N1—C1	0.8 (3)	C10—N2—C11—C12	176.5 (2)
N2—Ni1—N1—C1	177.9 (3)	Ni1—N2—C11—C12	−4.4 (3)
O4W—Ni1—N1—C1	86.7 (2)	N1—C12—C11—N2	−0.1 (4)
O1W—Ni1—N1—C12	87.52 (18)	C4—C12—C11—N2	−179.7 (2)
O3W—Ni1—N1—C12	37.8 (6)	N1—C12—C11—C7	179.1 (2)
O2W—Ni1—N1—C12	177.81 (18)	C4—C12—C11—C7	−0.6 (4)
N2—Ni1—N1—C12	−5.11 (16)	C12—N1—C1—C2	−0.6 (4)
O4W—Ni1—N1—C12	−96.31 (18)	Ni1—N1—C1—C2	176.2 (2)
C20—C17—C16—C24	−74.2 (2)	C3—C2—C1—N1	0.6 (4)
C18—C17—C16—C24	167.72 (19)	C10—C9—C8—C7	−0.1 (5)
C20—C17—C16—C15	55.7 (2)	C9—C8—C7—C11	−1.3 (5)
C18—C17—C16—C15	−62.3 (2)	C9—C8—C7—C6	−179.1 (3)
C1—N1—C12—C4	1.4 (4)	N2—C11—C7—C8	2.7 (4)
Ni1—N1—C12—C4	−175.9 (2)	C12—C11—C7—C8	−176.4 (3)
C1—N1—C12—C11	−178.2 (2)	N2—C11—C7—C6	−179.3 (3)
Ni1—N1—C12—C11	4.4 (3)	C12—C11—C7—C6	1.6 (4)
C14—C19—C20—C17	−0.5 (3)	C1—C2—C3—C4	−1.3 (5)
C18—C17—C20—C19	58.8 (3)	C12—C4—C3—C2	2.0 (5)
C16—C17—C20—C19	−57.7 (3)	C5—C4—C3—C2	−179.6 (3)
C17—C18—C22—O4	−7.5 (3)	C11—N2—C10—C9	1.1 (4)
C13—C18—C22—O4	117.9 (3)	Ni1—N2—C10—C9	−177.9 (2)
C17—C18—C22—O3	168.6 (2)	C8—C9—C10—N2	0.2 (4)
C13—C18—C22—O3	−66.0 (3)	C4—C5—C6—C7	−0.6 (6)
O6—C23—C15—C14	−63.2 (3)	C8—C7—C6—C5	176.8 (4)
O5—C23—C15—C14	113.8 (2)	C11—C7—C6—C5	−1.0 (6)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O7—H7···O3ⁱ	0.82	1.83	2.576 (3)	151
O1—H1···O6ⁱⁱ	0.82	1.88	2.670 (3)	163
O1W—HW11···O4	0.83 (2)	1.90 (2)	2.716 (3)	170 (3)
O1W—HW12···O5ⁱⁱⁱ	0.86 (2)	1.83 (2)	2.682 (3)	173 (3)
O4W—HW41···O5^iv	0.85 (2)	2.07 (3)	2.879 (3)	161 (4)
O4W—HW42···O3^v	0.85 (2)	2.16 (2)	2.926 (3)	150 (4)
O3W—HW31···O3^vi	0.86 (2)	1.96 (2)	2.814 (3)	171 (3)
O3W—HW32···O6ⁱⁱⁱ	0.85 (2)	2.06 (2)	2.893 (3)	166 (4)
O2W—HW21···O3^v	0.84 (2)	2.47 (2)	3.244 (4)	153 (4)
O2W—HW22···O2	0.85 (2)	2.01 (2)	2.806 (3)	154 (4)

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

Experimental details

Crystal data
Chemical formula	[Ni(C₁₂H₈N₂)(H₂O)₄](C₁₂H₁₀O₈)
M_r	593.18
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	7.446 (5), 13.583 (6), 22.982 (9)
β (°)	91.549 (7)
V (Å³)	2323.5 (18)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.91
Crystal size (mm)	0.30 × 0.28 × 0.17

Data collection
Diffractometer	Bruker APEX CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick 1996)
T_min, T_max	0.756, 0.855
No. of measured, independent and observed [I > 2σ(I)] reflections	14211, 5636, 4321
R_int	0.032
(sin θ/λ)_max (Å⁻¹)	0.667

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.133, 1.10
No. of reflections	5636
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)	0.46, −0.47

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O7—H7···O3ⁱ	0.82	1.83	2.576 (3)	151.0
O1—H1···O6ⁱⁱ	0.82	1.88	2.670 (3)	163.1
O1W—HW11···O4	0.828 (16)	1.897 (18)	2.716 (3)	170 (3)
O1W—HW12···O5ⁱⁱⁱ	0.859 (17)	1.828 (18)	2.682 (3)	173 (3)
O4W—HW41···O5^iv	0.845 (18)	2.07 (3)	2.879 (3)	161 (4)
O4W—HW42···O3^v	0.849 (18)	2.16 (2)	2.926 (3)	150 (4)
O3W—HW31···O3^vi	0.863 (17)	1.958 (17)	2.814 (3)	171 (3)
O3W—HW32···O6ⁱⁱⁱ	0.850 (17)	2.060 (19)	2.893 (3)	166 (4)
O2W—HW21···O3^v	0.844 (18)	2.47 (2)	3.244 (4)	153 (4)
O2W—HW22···O2	0.853 (18)	2.01 (2)	2.806 (3)	154 (4)

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

Acknowledgements

The authors thank the Science Foundation for Young Teachers of Northeast Normal University for support (grant No. 20080305).

References

Bruker (1998). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Liu, Y.-Y., Zhuo, Y.-J., Li, X.-Q. & Ma, J.-C. (2008). Acta Cryst. E64, m1590. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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

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