(μ-Butane-1,2,3,4-tetra-carboxyl-ato)bis-[triaqua-(1,10-phenanthroline)nickel(II)] hexa-hydrate.

The asymmetric unit of the title compound, [Ni(2)(C(8)H(6)O(8))(C(12)H(8)N(2))(2)(H(2)O)(6)]·6H(2)O, contains a half of the centrosymmetric dinuclear complex mol-ecule and three uncoordinated water mol-ecules. In the dinuclear mol-ecule, two Ni(II) cations are bridged by the butane-1,2,3,4-tetra-carboxyl-ate (BTC(4-)) anion. Each Ni(II) atom is coordinated by two N atoms from the 1,10-phenanthroline ligand, one O atom from the BTC(4-) anion and three aqua ligands in a distorted octa-hedral geometry. Inter-molecuar O-H⋯O hydrogen bonds and π-π stacking inter-ations [centroid-centroid distances = 3.646 (2), 3.781 (2) and 3.642 (2) Å] consolidate the crystal packing.

Related literature

For related structures, see: Chen et al. (2008 ▶); Ghosh et al. (2004 ▶); Fabelo et al. (2008 ▶); Zhu & Zheng (2010 ▶).

Experimental

Crystal data

[Ni2(C8H6O8)(C12H8N2)2(H2O)6]·6H2O

M = 924.15

Triclinic,

a = 9.0382 (18) Å

b = 9.5342 (19) Å

c = 12.253 (3) Å

α = 91.90 (3)°

β = 97.14 (3)°

γ = 111.54 (3)°

V = 971.0 (3) Å3

Z = 1

Mo Kα radiation

μ = 1.06 mm−1

T = 293 K

0.43 × 0.39 × 0.32 mm

Data collection

Rigaku R-AXIS RAPID diffractometer

Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.641, T max = 0.713

7940 measured reflections

4195 independent reflections

3499 reflections with I > 2σ(I)

R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.108

S = 1.17

4195 reflections

262 parameters

H-atom parameters constrained

Δρmax = 0.74 e Å−3

Δρmin = −0.48 e Å−3

Data collection: RAPID-AUTO (Rigaku, 1998 ▶); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004 ▶); 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: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810045137/cv2791sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810045137/cv2791Isup2.hkl

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

[Ni2(C8H6O8)(C12H8N2)2(H2O)6]·6H2O	Z = 1
Mr = 924.15	F(000) = 482
Triclinic, P1	Dx = 1.580 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.0382 (18) Å	Cell parameters from 6619 reflections
b = 9.5342 (19) Å	θ = 3.1–27.4°
c = 12.253 (3) Å	µ = 1.06 mm−1
α = 91.90 (3)°	T = 293 K
β = 97.14 (3)°	Block, green
γ = 111.54 (3)°	0.43 × 0.39 × 0.32 mm
V = 971.0 (3) Å3

Rigaku R-AXIS RAPID diffractometer	4195 independent reflections
Radiation source: fine-focus sealed tube	3499 reflections with I > 2σ(I)
graphite	Rint = 0.022
Detector resolution: 0 pixels mm-1	θmax = 27.4°, θmin = 3.1°
ω scans	h = −11→11
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	k = −12→10
Tmin = 0.641, Tmax = 0.713	l = −15→15
7940 measured reflections

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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.108	H-atom parameters constrained
S = 1.17	w = 1/[σ2(Fo2) + (0.0364P)2 + 1.1101P] where P = (Fo2 + 2Fc2)/3
4195 reflections	(Δ/σ)max = 0.001
262 parameters	Δρmax = 0.74 e Å−3
0 restraints	Δρmin = −0.48 e Å−3

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.

	x	y	z	Uiso*/Ueq
Ni	0.68724 (4)	0.80076 (4)	0.76505 (3)	0.02477 (12)
N1	0.6678 (3)	0.9786 (3)	0.67867 (18)	0.0276 (5)
N2	0.7744 (3)	0.7621 (3)	0.62136 (19)	0.0277 (5)
O5	0.5825 (3)	0.8507 (3)	0.89489 (17)	0.0423 (5)
H5B	0.4869	0.8552	0.8872	0.051*
H5C	0.6378	0.8539	0.9561	0.051*
O6	0.4684 (2)	0.6335 (2)	0.69310 (17)	0.0341 (5)
H6B	0.4833	0.5630	0.7195	0.041*
H6C	0.3783	0.6165	0.7092	0.041*
O7	0.9146 (2)	0.9445 (2)	0.84282 (16)	0.0293 (4)
H7B	0.9588	0.9008	0.8865	0.035*
H7C	0.9255	1.0310	0.8718	0.035*
O1	0.7521 (2)	0.6486 (2)	0.84846 (17)	0.0362 (5)
O2	0.5423 (2)	0.4320 (2)	0.8157 (2)	0.0425 (5)
C1	0.6809 (3)	0.5127 (3)	0.8629 (2)	0.0271 (6)
C2	0.7714 (3)	0.4396 (3)	0.9396 (2)	0.0290 (6)
H2A	0.7638	0.3446	0.9035	0.035*
H2B	0.7215	0.4176	1.0059	0.035*
C3	0.9509 (3)	0.5431 (3)	0.9717 (2)	0.0295 (6)
H3A	0.9948	0.5802	0.9044	0.035*
C4	0.9715 (3)	0.6820 (3)	1.0517 (2)	0.0309 (6)
O3	0.9006 (3)	0.6585 (2)	1.13534 (18)	0.0407 (5)
O4	1.0589 (3)	0.8098 (2)	1.02824 (17)	0.0347 (5)
C5	0.6195 (4)	1.0876 (4)	0.7097 (3)	0.0359 (7)
H5A	0.5862	1.0870	0.7786	0.043*
C6	0.6166 (4)	1.2032 (4)	0.6433 (3)	0.0434 (8)
H6A	0.5815	1.2773	0.6678	0.052*
C7	0.6657 (4)	1.2063 (4)	0.5420 (3)	0.0415 (8)
H7A	0.6635	1.2821	0.4967	0.050*
C8	0.7197 (4)	1.0935 (4)	0.5066 (2)	0.0347 (6)
C9	0.7752 (4)	1.0884 (4)	0.4024 (3)	0.0431 (8)
H9A	0.7787	1.1638	0.3554	0.052*
C10	0.8223 (4)	0.9765 (4)	0.3714 (2)	0.0427 (8)
H10A	0.8570	0.9755	0.3032	0.051*
C11	0.8201 (4)	0.8591 (4)	0.4419 (2)	0.0346 (7)
C12	0.8641 (4)	0.7363 (4)	0.4137 (3)	0.0432 (8)
H12A	0.8931	0.7258	0.3446	0.052*
C13	0.8637 (4)	0.6342 (4)	0.4880 (3)	0.0460 (8)
H13A	0.8919	0.5528	0.4698	0.055*
C14	0.8207 (4)	0.6510 (3)	0.5925 (3)	0.0361 (7)
H14A	0.8248	0.5817	0.6433	0.043*
C15	0.7721 (3)	0.8636 (3)	0.5468 (2)	0.0278 (6)
C16	0.7193 (3)	0.9821 (3)	0.5787 (2)	0.0265 (6)
O8	0.1691 (3)	0.5950 (3)	0.74263 (19)	0.0460 (6)
H8A	0.1488	0.5207	0.7791	0.055*
H8B	0.2014	0.6772	0.7847	0.055*
O9	0.6790 (3)	0.8105 (2)	0.10898 (17)	0.0368 (5)
H9B	0.6128	0.7421	0.1314	0.044*
H9C	0.7676	0.7992	0.1111	0.044*
O10	0.7218 (3)	0.1261 (3)	0.11685 (18)	0.0414 (5)
H10B	0.7796	0.1543	0.0685	0.050*
H10C	0.6930	0.0308	0.1270	0.050*

	U11	U22	U33	U12	U13	U23
Ni	0.02751 (19)	0.0260 (2)	0.02009 (18)	0.00896 (15)	0.00360 (12)	0.00473 (13)
N1	0.0332 (12)	0.0274 (12)	0.0232 (11)	0.0130 (10)	0.0028 (9)	0.0010 (9)
N2	0.0303 (12)	0.0245 (12)	0.0271 (11)	0.0088 (10)	0.0050 (9)	0.0010 (9)
O5	0.0404 (12)	0.0683 (16)	0.0246 (10)	0.0258 (12)	0.0092 (9)	0.0079 (10)
O6	0.0273 (10)	0.0366 (12)	0.0340 (11)	0.0079 (9)	0.0003 (8)	0.0058 (9)
O7	0.0298 (10)	0.0219 (9)	0.0316 (10)	0.0056 (8)	0.0010 (8)	−0.0010 (8)
O1	0.0333 (11)	0.0268 (11)	0.0411 (12)	0.0053 (9)	−0.0048 (9)	0.0126 (9)
O2	0.0284 (11)	0.0325 (12)	0.0570 (14)	0.0039 (10)	−0.0069 (10)	0.0115 (10)
C1	0.0299 (14)	0.0277 (14)	0.0254 (13)	0.0121 (12)	0.0061 (10)	0.0038 (11)
C2	0.0279 (14)	0.0259 (14)	0.0317 (14)	0.0088 (12)	0.0014 (11)	0.0065 (11)
C3	0.0286 (14)	0.0297 (15)	0.0299 (14)	0.0101 (12)	0.0051 (11)	0.0063 (11)
C4	0.0323 (14)	0.0278 (15)	0.0372 (15)	0.0141 (13)	0.0122 (12)	0.0042 (12)
O3	0.0549 (14)	0.0318 (11)	0.0429 (12)	0.0187 (11)	0.0256 (10)	0.0068 (9)
O4	0.0410 (12)	0.0183 (10)	0.0408 (12)	0.0043 (9)	0.0133 (9)	−0.0007 (8)
C5	0.0408 (17)	0.0344 (16)	0.0326 (15)	0.0155 (14)	0.0025 (12)	−0.0020 (12)
C6	0.052 (2)	0.0318 (17)	0.0468 (19)	0.0198 (16)	−0.0031 (15)	−0.0022 (14)
C7	0.0484 (19)	0.0286 (16)	0.0433 (18)	0.0126 (15)	−0.0047 (14)	0.0088 (13)
C8	0.0374 (16)	0.0332 (16)	0.0275 (14)	0.0081 (13)	−0.0024 (12)	0.0074 (12)
C9	0.0454 (18)	0.048 (2)	0.0273 (15)	0.0073 (16)	0.0024 (13)	0.0158 (14)
C10	0.0431 (18)	0.056 (2)	0.0204 (14)	0.0082 (16)	0.0061 (12)	0.0070 (13)
C11	0.0298 (14)	0.0429 (17)	0.0242 (14)	0.0065 (13)	0.0027 (11)	−0.0031 (12)
C12	0.0417 (17)	0.052 (2)	0.0313 (16)	0.0119 (16)	0.0088 (13)	−0.0114 (15)
C13	0.0459 (19)	0.047 (2)	0.048 (2)	0.0214 (17)	0.0077 (15)	−0.0147 (16)
C14	0.0389 (16)	0.0293 (15)	0.0414 (17)	0.0140 (13)	0.0071 (13)	0.0003 (13)
C15	0.0273 (13)	0.0307 (15)	0.0211 (12)	0.0067 (12)	0.0023 (10)	−0.0006 (10)
C16	0.0271 (13)	0.0255 (14)	0.0222 (13)	0.0051 (11)	0.0008 (10)	0.0021 (10)
O8	0.0597 (15)	0.0415 (13)	0.0427 (13)	0.0203 (12)	0.0224 (11)	0.0110 (10)
O9	0.0392 (12)	0.0368 (12)	0.0362 (11)	0.0151 (10)	0.0084 (9)	0.0080 (9)
O10	0.0485 (13)	0.0418 (13)	0.0422 (12)	0.0214 (11)	0.0208 (10)	0.0104 (10)

Ni—O1	2.017 (2)	C5—C6	1.397 (5)
Ni—O5	2.076 (2)	C5—H5A	0.9300
Ni—N1	2.078 (2)	C6—C7	1.367 (5)
Ni—O7	2.090 (2)	C6—H6A	0.9300
Ni—N2	2.091 (2)	C7—C8	1.410 (5)
Ni—O6	2.095 (2)	C7—H7A	0.9300
N1—C5	1.328 (4)	C8—C16	1.403 (4)
N1—C16	1.361 (3)	C8—C9	1.435 (4)
N2—C14	1.326 (4)	C9—C10	1.346 (5)
N2—C15	1.356 (4)	C9—H9A	0.9300
O5—H5B	0.8747	C10—C11	1.433 (5)
O5—H5C	0.8409	C10—H10A	0.9300
O6—H6B	0.8032	C11—C15	1.411 (4)
O6—H6C	0.8211	C11—C12	1.413 (5)
O7—H7B	0.8391	C12—C13	1.354 (5)
O7—H7C	0.8530	C12—H12A	0.9300
O1—C1	1.247 (3)	C13—C14	1.405 (5)
O2—C1	1.256 (3)	C13—H13A	0.9300
C1—C2	1.519 (4)	C14—H14A	0.9300
C2—C3	1.549 (4)	C15—C16	1.439 (4)
C2—H2A	0.9700	O8—H8A	0.8255
C2—H2B	0.9700	O8—H8B	0.8567
C3—C3i	1.537 (5)	O9—H9B	0.7902
C3—C4	1.561 (4)	O9—H9C	0.8441
C3—H3A	0.9800	O10—H10B	0.8251
C4—O4	1.251 (4)	O10—H10C	0.8664
C4—O3	1.259 (4)
Cg1···Cg1ii	3.646 (2)	Cg2···Cg3iii	3.642 (2)
Cg1···Cg3ii	3.781 (2)
O1—Ni—O5	92.22 (10)	C2—C3—H3A	108.5
O1—Ni—N1	168.90 (9)	C4—C3—H3A	108.5
O5—Ni—N1	93.36 (9)	O4—C4—O3	124.4 (3)
O1—Ni—O7	81.02 (8)	O4—C4—C3	117.3 (2)
O5—Ni—O7	90.53 (9)	O3—C4—C3	118.3 (3)
N1—Ni—O7	89.35 (9)	N1—C5—C6	122.8 (3)
O1—Ni—N2	94.72 (10)	N1—C5—H5A	118.6
O5—Ni—N2	172.60 (9)	C6—C5—H5A	118.6
N1—Ni—N2	80.24 (9)	C7—C6—C5	119.4 (3)
O7—Ni—N2	93.08 (9)	C7—C6—H6A	120.3
O1—Ni—O6	91.78 (9)	C5—C6—H6A	120.3
O5—Ni—O6	91.48 (9)	C6—C7—C8	119.4 (3)
N1—Ni—O6	97.65 (9)	C6—C7—H7A	120.3
O7—Ni—O6	172.59 (8)	C8—C7—H7A	120.3
N2—Ni—O6	85.75 (9)	C16—C8—C7	117.4 (3)
C5—N1—C16	118.2 (3)	C16—C8—C9	119.2 (3)
C5—N1—Ni	129.1 (2)	C7—C8—C9	123.4 (3)
C16—N1—Ni	112.61 (18)	C10—C9—C8	121.2 (3)
C14—N2—C15	117.9 (3)	C10—C9—H9A	119.4
C14—N2—Ni	129.5 (2)	C8—C9—H9A	119.4
C15—N2—Ni	112.43 (18)	C9—C10—C11	121.1 (3)
Ni—O5—H5B	123.9	C9—C10—H10A	119.4
Ni—O5—H5C	111.3	C11—C10—H10A	119.4
H5B—O5—H5C	124.2	C15—C11—C12	116.6 (3)
Ni—O6—H6B	96.9	C15—C11—C10	119.3 (3)
Ni—O6—H6C	128.3	C12—C11—C10	124.2 (3)
H6B—O6—H6C	98.2	C13—C12—C11	119.6 (3)
Ni—O7—H7B	112.7	C13—C12—H12A	120.2
Ni—O7—H7C	118.6	C11—C12—H12A	120.2
H7B—O7—H7C	110.8	C12—C13—C14	120.0 (3)
C1—O1—Ni	133.77 (19)	C12—C13—H13A	120.0
O1—C1—O2	124.4 (3)	C14—C13—H13A	120.0
O1—C1—C2	117.3 (2)	N2—C14—C13	122.4 (3)
O2—C1—C2	118.3 (3)	N2—C14—H14A	118.8
C1—C2—C3	111.9 (2)	C13—C14—H14A	118.8
C1—C2—H2A	109.2	N2—C15—C11	123.4 (3)
C3—C2—H2A	109.2	N2—C15—C16	117.2 (2)
C1—C2—H2B	109.2	C11—C15—C16	119.3 (3)
C3—C2—H2B	109.2	N1—C16—C8	122.7 (3)
H2A—C2—H2B	107.9	N1—C16—C15	117.4 (2)
C3i—C3—C2	111.6 (3)	C8—C16—C15	119.9 (3)
C3i—C3—C4	108.1 (3)	H8A—O8—H8B	111.0
C2—C3—C4	111.4 (2)	H9B—O9—H9C	112.7
C3i—C3—H3A	108.5	H10B—O10—H10C	114.8

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5B···O10iv	0.87	1.95	2.826 (4)	175
O5—H5C···O9v	0.84	1.95	2.745 (3)	157
O6—H6B···O2	0.80	1.91	2.698 (3)	165
O6—H6C···O8	0.82	1.92	2.741 (4)	175
O7—H7B···O4	0.84	2.21	3.033 (3)	168
O7—H7C···O4vi	0.85	1.87	2.700 (3)	163
O8—H8A···O3vii	0.83	1.97	2.798 (3)	179
O8—H8B···O10iv	0.86	2.03	2.891 (4)	179
O9—H9B···O2iv	0.79	1.93	2.721 (3)	177
O9—H9C···O3viii	0.84	2.11	2.867 (4)	149
O10—H10B···O4ix	0.82	1.93	2.743 (3)	166
O10—H10C···O9x	0.87	2.06	2.886 (3)	159

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O5—H5B⋯O10i	0.87	1.95	2.826 (4)	175
O5—H5C⋯O9ii	0.84	1.95	2.745 (3)	157
O6—H6B⋯O2	0.80	1.91	2.698 (3)	165
O6—H6C⋯O8	0.82	1.92	2.741 (4)	175
O7—H7B⋯O4	0.84	2.21	3.033 (3)	168
O7—H7C⋯O4iii	0.85	1.87	2.700 (3)	163
O8—H8A⋯O3iv	0.83	1.97	2.798 (3)	179
O8—H8B⋯O10i	0.86	2.03	2.891 (4)	179
O9—H9B⋯O2i	0.79	1.93	2.721 (3)	177
O9—H9C⋯O3v	0.84	2.11	2.867 (4)	149
O10—H10B⋯O4vi	0.82	1.93	2.743 (3)	166
O10—H10C⋯O9vii	0.87	2.06	2.886 (3)	159

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) ; (vi) ; (vii) .