Crystal structure of poly[aqua­[μ-1,1′-(9,9-dimethyl-9H-fluoren-2,7-di­yl)di-1H-imidazole](μ-naphthalene-1,4-di­carboxyl­ato)nickel(II)]

Zou, H.; Qi, Y.

doi:10.1107/S1600536814017681

metal-organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 70| Part 9| September 2014| Pages m324-m325

doi:10.1107/S1600536814017681

Open

access

Crystal structure of poly[aqua[μ-1,1′-(9,9-dimethyl-9H-fluoren-2,7-diyl)di-1H-imidazole](μ-naphthalene-1,4-dicarboxylato)nickel(II)]

Hengye Zou ^a and Yanjuan Qi ^a ^*

^aDepartment of Chemistry, Changchun Normal University, Changchun 130032, People's Republic of China
^*Correspondence e-mail: qiyjchem@163.com

Edited by C. Näther, Universität Kiel, Germany (Received 7 July 2014; accepted 1 August 2014; online 6 August 2014)

In the title compound, [Ni(C₁₂H₆O₄)(C₂₁H₁₈N₄)(H₂O)]_n, the Ni^II cation is coordinated by three carboxylate O atoms of two naphthalene-1,4-dicarboxylate anions, one water molecule and two N atoms of two 1,1′-(9,9-dimethyl-9H-fluoren-2,7-diyl)di-1H-imidazole (DFDI) ligands, giving rise to a slightly distorted octahedral geometry. The Ni^II ions are linked by the DFDI ligands into chains, which are further connected by the carboxylate anions into double chains that elongate in the the b-axis direction. These double chains are linked by centrosymmetric pairs of O—H⋯O hydrogen bonds into layers parallel to (10-1). The asymmetric unit consists of one crystallographically independent Ni^II cation, one carboxylate and one DFDI ligand, as well as of one water molecule, all of them located in general positions.

Keywords: crystal structure; nickel complex; naphthalene-1,4-dicarboxylate; hydrogen bonding; double chain.

CCDC reference: 1017498

1. Related literature

For the synthesis and structures of related Ni and naphthalenedicarboxylates, see: Guo et al. (2013 ); Kaduk & Hanko (2001 ).

2. Experimental

2.1. Crystal data

[Ni(C₁₂H₆O₄)(C₂₁H₁₈N₄)(H₂O)]
M_r = 617.29
Monoclinic, P 2₁ /n
a = 11.1696 (17) Å
b = 16.161 (2) Å
c = 16.004 (2) Å
β = 93.458 (3)°
V = 2883.6 (7) Å³
Z = 4
Mo Kα radiation
μ = 0.72 mm⁻¹
T = 293 K
0.30 × 0.24 × 0.21 mm

2.2. Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2002 ) T_min = 0.801, T_max = 0.865
18236 measured reflections
7043 independent reflections
4614 reflections with I > 2σ(I)
R_int = 0.053

2.3. Refinement

R[F² > 2σ(F²)] = 0.058
wR(F²) = 0.167
S = 1.00
7043 reflections
394 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 1.24 e Å⁻³
Δρ_min = −0.80 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1A⋯O1	0.85 (1)	1.88 (2)	2.659 (3)	152 (4)
O1W—H1B⋯O4ⁱ	0.85 (1)	1.94 (1)	2.791 (3)	176 (4)
Symmetry code: (i) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2008 ); software used to prepare material for publication: SHELXTL and publCIF (Westrip, 2010 ).

Supporting information

CCDC reference: 1017498

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536814017681/nc2327sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814017681/nc2327Isup2.hkl

checkCIF report

Synthesis and crystallization top

The synthesis was performed under hydrothermal conditions. A mixture of Ni(CH₃COO)₂^.4(H₂O), (0.2 mmol, 0.05 g), naphthalene-1,4-dicarboxylic acid (0.2 mmol, 0.044 g), 9,9-dimethyl-9H-fluorene-2,7-diimidazole (0.2 mmol, 0.064 g) and H₂O (15 mL) in a 25 mL stainless steel reactor with a Teflon liner was heated from 293 to 453 K in 2 h and a constant temperature was maintained at 453 K for 72 h, after which the mixture was cooled to 298 K. Green crystals of the title compound were recovered from the reaction.

Refinement top

All C—H H atoms were positioned with idealized geometry and refined isotropic with U_iso(H) = 1.2 U_eq(C) (1.5 for methyl H atoms) using a riding model. The water H-atoms were located in a difference map and were refined with an O—H distance restrained to 0.85 (2) Å and with [U_iso(H) = 1.5 U_eq(O)].

Related literature top

For the synthesis and structures of related Ni and naphthalenedicarboxylates, see: Guo et al. (2013); Kaduk & Hanko (2001).

Computing details top

Data collection: APEX2 (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and publCIF (Westrip, 2010).

Figures top

	Fig. 1. A view of the molecule of the title compound. Displacement ellipsoids are drawn at the 30% probability level. (i) -x + 1/2, y - 1/2, -z + 3/2; (ii) x, y - 1, z; (iii) x, y + 1, z.
	Fig. 2. Crystal structure of the title compound with view along the a-axis. Hydrogen atoms are omitted for clarity.

Poly[aqua[µ-1,1'-(9,9-dimethyl-9H-fluoren-2,7-diyl)di-1H-imidazole](µ-naphthalene-1,4-dicarboxylato)nickel(II)] top

Crystal data top

[Ni(C₁₂H₆O₄)(C₂₁H₁₈N₄)(H₂O)]	F(000) = 1280
M_r = 617.29	D_x = 1.422 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 7293 reflections
a = 11.1696 (17) Å	θ = 1.7–22.8°
b = 16.161 (2) Å	µ = 0.72 mm⁻¹
c = 16.004 (2) Å	T = 293 K
β = 93.458 (3)°	Block, green
V = 2883.6 (7) Å³	0.30 × 0.24 × 0.21 mm
Z = 4

Data collection top

Bruker SMART APEXII CCD diffractometer	7043 independent reflections
Radiation source: fine-focus sealed tube	4614 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.053
phi and ω scans	θ_max = 28.5°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2002)	h = −14→10
T_min = 0.801, T_max = 0.865	k = −20→21
18236 measured reflections	l = −15→21

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)] = 0.058	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.167	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ²(F_o²) + (0.0959P)²] where P = (F_o² + 2F_c²)/3
7043 reflections	(Δ/σ)_max = 0.001
394 parameters	Δρ_max = 1.24 e Å⁻³
2 restraints	Δρ_min = −0.80 e Å⁻³

Crystal data top

[Ni(C₁₂H₆O₄)(C₂₁H₁₈N₄)(H₂O)]	V = 2883.6 (7) Å³
M_r = 617.29	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 11.1696 (17) Å	µ = 0.72 mm⁻¹
b = 16.161 (2) Å	T = 293 K
c = 16.004 (2) Å	0.30 × 0.24 × 0.21 mm
β = 93.458 (3)°

Data collection top

Bruker SMART APEXII CCD diffractometer	7043 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2002)	4614 reflections with I > 2σ(I)
T_min = 0.801, T_max = 0.865	R_int = 0.053
18236 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.058	2 restraints
wR(F²) = 0.167	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	Δρ_max = 1.24 e Å⁻³
7043 reflections	Δρ_min = −0.80 e Å⁻³
394 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	0.27771 (4)	0.06178 (2)	0.98863 (2)	0.02497 (14)
C1	0.3429 (3)	0.21356 (19)	0.88921 (19)	0.0279 (7)
C2	0.3086 (3)	0.27180 (18)	0.81633 (18)	0.0257 (7)
C3	0.3433 (3)	0.35240 (19)	0.8250 (2)	0.0316 (7)
H3	0.3853	0.3687	0.8742	0.038*
C4	0.3180 (3)	0.4110 (2)	0.7628 (2)	0.0325 (8)
H4	0.3430	0.4654	0.7712	0.039*
C5	0.2566 (3)	0.38957 (19)	0.68914 (19)	0.0262 (7)
C6	0.2184 (3)	0.30647 (18)	0.67658 (19)	0.0260 (7)
C7	0.2414 (3)	0.24588 (18)	0.74100 (18)	0.0247 (6)
C8	0.1991 (3)	0.1646 (2)	0.7261 (2)	0.0346 (8)
H8	0.2118	0.1247	0.7676	0.042*
C9	0.1399 (4)	0.1433 (2)	0.6520 (2)	0.0408 (9)
H9	0.1115	0.0896	0.6440	0.049*
C10	0.1217 (4)	0.2020 (2)	0.5879 (2)	0.0417 (9)
H10	0.0828	0.1868	0.5372	0.050*
C11	0.1606 (3)	0.2807 (2)	0.59974 (19)	0.0313 (7)
H11	0.1491	0.3187	0.5564	0.038*
C12	0.2384 (3)	0.45528 (18)	0.62262 (19)	0.0259 (7)
C13	0.1741 (3)	0.2175 (2)	1.0487 (2)	0.0391 (9)
H13	0.2352	0.2454	1.0236	0.047*
C14	0.0603 (3)	0.1215 (2)	1.0900 (2)	0.0363 (8)
H14	0.0281	0.0694	1.0989	0.044*
C15	0.0164 (3)	0.1935 (2)	1.1183 (2)	0.0412 (9)
H15	−0.0506	0.2000	1.1495	0.049*
C16	0.0811 (3)	0.3425 (2)	1.1046 (2)	0.0321 (7)
C17	−0.0300 (3)	0.3811 (2)	1.1055 (3)	0.0431 (9)
H17	−0.1000	0.3499	1.0996	0.052*
C18	−0.0362 (3)	0.4668 (2)	1.1155 (3)	0.0451 (10)
H18	−0.1101	0.4930	1.1176	0.054*
C19	0.0692 (3)	0.5122 (2)	1.1223 (2)	0.0362 (8)
C20	0.1806 (3)	0.4719 (2)	1.1219 (2)	0.0316 (7)
C21	0.1867 (3)	0.38737 (19)	1.1146 (2)	0.0328 (7)
H21	0.2605	0.3606	1.1164	0.039*
C22	0.2840 (3)	0.5320 (2)	1.1301 (2)	0.0322 (7)
C23	0.3652 (4)	0.5239 (2)	1.0574 (3)	0.0451 (9)
H23A	0.4298	0.5629	1.0643	0.068*
H23B	0.3197	0.5350	1.0057	0.068*
H23C	0.3971	0.4688	1.0562	0.068*
C24	0.3560 (4)	0.5212 (2)	1.2141 (2)	0.0462 (9)
H24A	0.4210	0.5601	1.2178	0.069*
H24B	0.3873	0.4660	1.2181	0.069*
H24C	0.3046	0.5308	1.2591	0.069*
C25	0.2157 (3)	0.6146 (2)	1.1293 (2)	0.0349 (8)
C26	0.0924 (3)	0.6021 (2)	1.1263 (2)	0.0365 (8)
C27	0.0149 (4)	0.6698 (2)	1.1260 (3)	0.0477 (10)
H27	−0.0676	0.6620	1.1253	0.057*
C28	0.0631 (4)	0.7491 (2)	1.1265 (3)	0.0454 (10)
H28	0.0127	0.7949	1.1263	0.054*
C29	0.1852 (3)	0.7599 (2)	1.1273 (2)	0.0366 (8)
C30	0.2639 (3)	0.69321 (19)	1.1287 (2)	0.0343 (8)
H30	0.3463	0.7013	1.1293	0.041*
C31	0.1982 (3)	0.9034 (2)	1.0717 (2)	0.0361 (8)
H31	0.1278	0.9016	1.0376	0.043*
C32	0.3630 (4)	0.9439 (2)	1.1328 (2)	0.0381 (8)
H32	0.4286	0.9768	1.1491	0.046*
C33	0.3425 (4)	0.8680 (2)	1.1618 (2)	0.0428 (9)
H33	0.3912	0.8387	1.2005	0.051*
N1	0.1599 (3)	0.13708 (16)	1.04611 (17)	0.0311 (6)
N2	0.0896 (3)	0.25512 (16)	1.09216 (17)	0.0327 (6)
N3	0.2357 (3)	0.84159 (16)	1.12350 (17)	0.0334 (7)
N4	0.2723 (3)	0.96596 (16)	1.07513 (17)	0.0320 (6)
O1	0.4258 (3)	0.23703 (16)	0.93909 (16)	0.0480 (7)
O2	0.2836 (2)	0.14906 (14)	0.89537 (13)	0.0362 (6)
O3	0.3289 (2)	0.49273 (13)	0.59960 (14)	0.0303 (5)
O4	0.1345 (2)	0.47139 (14)	0.59113 (14)	0.0324 (5)
O1W	0.4228 (2)	0.11528 (14)	1.05066 (15)	0.0347 (6)
H1A	0.433 (4)	0.1628 (12)	1.030 (2)	0.052*
H1B	0.488 (2)	0.089 (2)	1.060 (3)	0.052*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ni1	0.0363 (3)	0.0194 (2)	0.0184 (2)	−0.00295 (17)	−0.00517 (16)	−0.00024 (14)
C1	0.0347 (18)	0.0284 (16)	0.0200 (15)	−0.0009 (14)	−0.0045 (13)	0.0032 (12)
C2	0.0313 (17)	0.0266 (16)	0.0186 (15)	−0.0008 (13)	−0.0031 (12)	0.0037 (11)
C3	0.042 (2)	0.0285 (17)	0.0228 (16)	−0.0043 (14)	−0.0094 (14)	0.0027 (12)
C4	0.044 (2)	0.0213 (15)	0.0312 (18)	−0.0038 (14)	−0.0074 (15)	0.0014 (13)
C5	0.0298 (17)	0.0253 (16)	0.0229 (16)	0.0032 (13)	−0.0029 (13)	0.0031 (12)
C6	0.0298 (17)	0.0227 (15)	0.0248 (16)	0.0042 (12)	−0.0034 (13)	0.0018 (12)
C7	0.0281 (16)	0.0257 (15)	0.0201 (15)	0.0007 (13)	−0.0012 (12)	0.0011 (11)
C8	0.051 (2)	0.0281 (17)	0.0236 (17)	−0.0022 (15)	−0.0080 (15)	0.0046 (13)
C9	0.061 (3)	0.0276 (18)	0.0322 (19)	−0.0095 (16)	−0.0139 (17)	0.0017 (14)
C10	0.058 (2)	0.036 (2)	0.0280 (18)	0.0009 (17)	−0.0164 (17)	−0.0028 (14)
C11	0.0383 (19)	0.0304 (17)	0.0238 (16)	0.0065 (14)	−0.0080 (14)	0.0039 (13)
C12	0.0343 (18)	0.0199 (15)	0.0229 (16)	0.0050 (12)	−0.0033 (13)	−0.0019 (11)
C13	0.048 (2)	0.0261 (17)	0.045 (2)	−0.0079 (15)	0.0165 (17)	−0.0048 (15)
C14	0.0361 (19)	0.0251 (17)	0.047 (2)	−0.0066 (14)	0.0017 (16)	0.0033 (15)
C15	0.036 (2)	0.036 (2)	0.053 (2)	−0.0067 (16)	0.0144 (17)	0.0021 (16)
C16	0.0396 (19)	0.0251 (16)	0.0321 (18)	−0.0031 (14)	0.0069 (15)	−0.0033 (13)
C17	0.034 (2)	0.0336 (19)	0.062 (3)	−0.0042 (16)	0.0066 (18)	−0.0045 (17)
C18	0.033 (2)	0.0310 (19)	0.072 (3)	0.0013 (16)	0.0112 (19)	−0.0045 (18)
C19	0.038 (2)	0.0272 (18)	0.044 (2)	0.0015 (14)	0.0075 (16)	0.0007 (14)
C20	0.0365 (19)	0.0278 (16)	0.0306 (18)	−0.0030 (14)	0.0027 (14)	0.0002 (13)
C21	0.0341 (19)	0.0262 (17)	0.0387 (19)	0.0017 (14)	0.0062 (15)	0.0005 (13)
C22	0.0342 (19)	0.0253 (16)	0.0372 (19)	−0.0034 (14)	0.0034 (15)	0.0010 (13)
C23	0.048 (2)	0.038 (2)	0.051 (2)	−0.0016 (17)	0.0150 (19)	−0.0010 (17)
C24	0.045 (2)	0.042 (2)	0.051 (2)	−0.0063 (18)	−0.0086 (18)	0.0022 (17)
C25	0.041 (2)	0.0267 (17)	0.037 (2)	−0.0019 (15)	0.0054 (16)	0.0014 (14)
C26	0.037 (2)	0.0293 (18)	0.044 (2)	−0.0020 (15)	0.0080 (16)	−0.0014 (15)
C27	0.041 (2)	0.0310 (19)	0.072 (3)	0.0023 (16)	0.007 (2)	0.0005 (18)
C28	0.046 (2)	0.0292 (19)	0.062 (3)	0.0064 (17)	0.011 (2)	0.0000 (17)
C29	0.052 (2)	0.0249 (17)	0.0331 (19)	−0.0045 (15)	0.0048 (16)	0.0005 (13)
C30	0.039 (2)	0.0275 (17)	0.0363 (19)	−0.0031 (15)	0.0044 (15)	0.0022 (14)
C31	0.045 (2)	0.0282 (17)	0.0350 (19)	−0.0012 (15)	−0.0026 (16)	0.0047 (14)
C32	0.053 (2)	0.0317 (18)	0.0288 (18)	−0.0091 (16)	−0.0068 (16)	0.0026 (14)
C33	0.057 (2)	0.036 (2)	0.034 (2)	−0.0008 (18)	−0.0058 (18)	0.0041 (15)
N1	0.0364 (16)	0.0278 (14)	0.0286 (15)	−0.0027 (12)	−0.0017 (12)	−0.0020 (11)
N2	0.0374 (16)	0.0243 (14)	0.0367 (16)	−0.0040 (12)	0.0062 (13)	−0.0036 (11)
N3	0.0488 (18)	0.0229 (13)	0.0286 (15)	−0.0007 (12)	0.0026 (13)	0.0038 (11)
N4	0.0475 (18)	0.0246 (14)	0.0235 (14)	−0.0041 (13)	−0.0009 (12)	−0.0014 (11)
O1	0.0564 (17)	0.0449 (15)	0.0391 (15)	−0.0187 (13)	−0.0280 (12)	0.0196 (11)
O2	0.0568 (16)	0.0293 (12)	0.0210 (12)	−0.0104 (11)	−0.0115 (11)	0.0078 (9)
O3	0.0333 (13)	0.0252 (11)	0.0316 (13)	0.0023 (10)	−0.0049 (10)	0.0072 (9)
O4	0.0338 (13)	0.0294 (12)	0.0327 (13)	0.0021 (10)	−0.0084 (10)	0.0050 (9)
O1W	0.0399 (14)	0.0281 (13)	0.0346 (13)	−0.0050 (11)	−0.0107 (11)	0.0041 (10)

Geometric parameters (Å, º) top

Ni1—O1W	2.041 (2)	C17—C18	1.397 (5)
Ni1—N1	2.050 (3)	C17—H17	0.9300
Ni1—O2	2.058 (2)	C18—C19	1.387 (5)
Ni1—N4ⁱ	2.080 (3)	C18—H18	0.9300
Ni1—O3ⁱⁱ	2.111 (2)	C19—C20	1.405 (5)
Ni1—O4ⁱⁱ	2.208 (2)	C19—C26	1.477 (5)
Ni1—C12ⁱⁱ	2.475 (3)	C20—C21	1.373 (5)
C1—O2	1.242 (4)	C20—C22	1.509 (5)
C1—O1	1.245 (4)	C21—H21	0.9300
C1—C2	1.529 (4)	C22—C23	1.524 (5)
C2—C3	1.364 (4)	C22—C24	1.534 (5)
C2—C7	1.443 (4)	C22—C25	1.536 (5)
C3—C4	1.391 (4)	C23—H23A	0.9600
C3—H3	0.9300	C23—H23B	0.9600
C4—C5	1.372 (4)	C23—H23C	0.9600
C4—H4	0.9300	C24—H24A	0.9600
C5—C6	1.420 (4)	C24—H24B	0.9600
C5—C12	1.509 (4)	C24—H24C	0.9600
C6—C11	1.417 (4)	C25—C30	1.380 (4)
C6—C7	1.434 (4)	C25—C26	1.390 (5)
C7—C8	1.411 (4)	C26—C27	1.394 (5)
C8—C9	1.367 (5)	C27—C28	1.391 (5)
C8—H8	0.9300	C27—H27	0.9300
C9—C10	1.403 (5)	C28—C29	1.374 (5)
C9—H9	0.9300	C28—H28	0.9300
C10—C11	1.354 (5)	C29—C30	1.389 (5)
C10—H10	0.9300	C29—N3	1.439 (4)
C11—H11	0.9300	C30—H30	0.9300
C12—O3	1.253 (4)	C31—N4	1.306 (4)
C12—O4	1.264 (4)	C31—N3	1.348 (4)
C12—Ni1ⁱⁱⁱ	2.475 (3)	C31—H31	0.9300
C13—N1	1.309 (4)	C32—C33	1.336 (5)
C13—N2	1.350 (4)	C32—N4	1.375 (5)
C13—H13	0.9300	C32—H32	0.9300
C14—C15	1.351 (5)	C33—N3	1.375 (5)
C14—N1	1.375 (4)	C33—H33	0.9300
C14—H14	0.9300	N4—Ni1^iv	2.080 (3)
C15—N2	1.370 (4)	O3—Ni1ⁱⁱⁱ	2.111 (2)
C15—H15	0.9300	O4—Ni1ⁱⁱⁱ	2.208 (2)
C16—C21	1.386 (5)	O1W—H1A	0.848 (10)
C16—C17	1.390 (5)	O1W—H1B	0.851 (10)
C16—N2	1.430 (4)

O1W—Ni1—N1	92.43 (11)	C19—C18—C17	119.1 (3)
O1W—Ni1—O2	90.18 (9)	C19—C18—H18	120.4
N1—Ni1—O2	88.17 (11)	C17—C18—H18	120.4
O1W—Ni1—N4ⁱ	92.62 (10)	C18—C19—C20	120.1 (3)
N1—Ni1—N4ⁱ	95.62 (11)	C18—C19—C26	132.1 (3)
O2—Ni1—N4ⁱ	175.18 (10)	C20—C19—C26	107.7 (3)
O1W—Ni1—O3ⁱⁱ	161.60 (10)	C21—C20—C19	120.7 (3)
N1—Ni1—O3ⁱⁱ	105.22 (10)	C21—C20—C22	127.3 (3)
O2—Ni1—O3ⁱⁱ	85.34 (9)	C19—C20—C22	111.9 (3)
N4ⁱ—Ni1—O3ⁱⁱ	90.79 (9)	C20—C21—C16	118.9 (3)
O1W—Ni1—O4ⁱⁱ	101.21 (9)	C20—C21—H21	120.5
N1—Ni1—O4ⁱⁱ	166.24 (10)	C16—C21—H21	120.5
O2—Ni1—O4ⁱⁱ	89.96 (9)	C20—C22—C23	111.5 (3)
N4ⁱ—Ni1—O4ⁱⁱ	85.64 (10)	C20—C22—C24	111.1 (3)
O3ⁱⁱ—Ni1—O4ⁱⁱ	61.03 (8)	C23—C22—C24	110.8 (3)
O1W—Ni1—C12ⁱⁱ	131.73 (11)	C20—C22—C25	100.5 (3)
N1—Ni1—C12ⁱⁱ	135.62 (11)	C23—C22—C25	112.7 (3)
O2—Ni1—C12ⁱⁱ	87.65 (9)	C24—C22—C25	109.9 (3)
N4ⁱ—Ni1—C12ⁱⁱ	87.55 (10)	C22—C23—H23A	109.5
O3ⁱⁱ—Ni1—C12ⁱⁱ	30.40 (10)	C22—C23—H23B	109.5
O4ⁱⁱ—Ni1—C12ⁱⁱ	30.64 (9)	H23A—C23—H23B	109.5
O2—C1—O1	125.7 (3)	C22—C23—H23C	109.5
O2—C1—C2	117.9 (3)	H23A—C23—H23C	109.5
O1—C1—C2	116.4 (3)	H23B—C23—H23C	109.5
C3—C2—C7	119.5 (3)	C22—C24—H24A	109.5
C3—C2—C1	117.0 (3)	C22—C24—H24B	109.5
C7—C2—C1	123.5 (3)	H24A—C24—H24B	109.5
C2—C3—C4	122.2 (3)	C22—C24—H24C	109.5
C2—C3—H3	118.9	H24A—C24—H24C	109.5
C4—C3—H3	118.9	H24B—C24—H24C	109.5
C5—C4—C3	120.8 (3)	C30—C25—C26	121.2 (3)
C5—C4—H4	119.6	C30—C25—C22	127.4 (3)
C3—C4—H4	119.6	C26—C25—C22	111.4 (3)
C4—C5—C6	119.4 (3)	C25—C26—C27	120.0 (3)
C4—C5—C12	117.8 (3)	C25—C26—C19	108.3 (3)
C6—C5—C12	122.7 (3)	C27—C26—C19	131.6 (3)
C11—C6—C5	121.2 (3)	C28—C27—C26	118.9 (4)
C11—C6—C7	118.4 (3)	C28—C27—H27	120.6
C5—C6—C7	120.3 (3)	C26—C27—H27	120.6
C8—C7—C6	118.1 (3)	C29—C28—C27	120.0 (3)
C8—C7—C2	124.3 (3)	C29—C28—H28	120.0
C6—C7—C2	117.6 (3)	C27—C28—H28	120.0
C9—C8—C7	121.4 (3)	C28—C29—C30	121.9 (3)
C9—C8—H8	119.3	C28—C29—N3	120.5 (3)
C7—C8—H8	119.3	C30—C29—N3	117.6 (3)
C8—C9—C10	120.3 (3)	C25—C30—C29	117.9 (3)
C8—C9—H9	119.8	C25—C30—H30	121.0
C10—C9—H9	119.8	C29—C30—H30	121.1
C11—C10—C9	120.2 (3)	N4—C31—N3	112.0 (3)
C11—C10—H10	119.9	N4—C31—H31	124.0
C9—C10—H10	119.9	N3—C31—H31	124.0
C10—C11—C6	121.6 (3)	C33—C32—N4	109.6 (3)
C10—C11—H11	119.2	C33—C32—H32	125.2
C6—C11—H11	119.2	N4—C32—H32	125.2
O3—C12—O4	121.4 (3)	C32—C33—N3	107.1 (3)
O3—C12—C5	118.1 (3)	C32—C33—H33	126.5
O4—C12—C5	120.5 (3)	N3—C33—H33	126.5
O3—C12—Ni1ⁱⁱⁱ	58.50 (15)	C13—N1—C14	105.4 (3)
O4—C12—Ni1ⁱⁱⁱ	62.91 (16)	C13—N1—Ni1	121.6 (2)
C5—C12—Ni1ⁱⁱⁱ	176.3 (2)	C14—N1—Ni1	133.0 (2)
N1—C13—N2	112.1 (3)	C13—N2—C15	106.2 (3)
N1—C13—H13	123.9	C13—N2—C16	124.8 (3)
N2—C13—H13	123.9	C15—N2—C16	129.0 (3)
C15—C14—N1	109.6 (3)	C31—N3—C33	105.8 (3)
C15—C14—H14	125.2	C31—N3—C29	126.7 (3)
N1—C14—H14	125.2	C33—N3—C29	126.7 (3)
C14—C15—N2	106.7 (3)	C31—N4—C32	105.5 (3)
C14—C15—H15	126.6	C31—N4—Ni1^iv	126.3 (2)
N2—C15—H15	126.6	C32—N4—Ni1^iv	126.1 (2)
C21—C16—C17	121.2 (3)	C1—O2—Ni1	132.4 (2)
C21—C16—N2	118.0 (3)	C12—O3—Ni1ⁱⁱⁱ	91.11 (18)
C17—C16—N2	120.8 (3)	C12—O4—Ni1ⁱⁱⁱ	86.45 (19)
C16—C17—C18	119.8 (3)	Ni1—O1W—H1A	108 (3)
C16—C17—H17	120.1	Ni1—O1W—H1B	122 (3)
C18—C17—H17	120.1	H1A—O1W—H1B	113 (4)

O2—C1—C2—C3	158.1 (3)	C22—C25—C26—C19	−1.8 (4)
O1—C1—C2—C3	−19.3 (5)	C18—C19—C26—C25	−177.5 (4)
O2—C1—C2—C7	−21.1 (5)	C20—C19—C26—C25	−0.7 (4)
O1—C1—C2—C7	161.4 (3)	C18—C19—C26—C27	1.2 (7)
C7—C2—C3—C4	−1.2 (5)	C20—C19—C26—C27	178.0 (4)
C1—C2—C3—C4	179.6 (3)	C25—C26—C27—C28	1.5 (6)
C2—C3—C4—C5	−0.2 (6)	C19—C26—C27—C28	−177.0 (4)
C3—C4—C5—C6	0.1 (5)	C26—C27—C28—C29	0.1 (6)
C3—C4—C5—C12	−176.7 (3)	C27—C28—C29—C30	−0.9 (6)
C4—C5—C6—C11	−176.5 (3)	C27—C28—C29—N3	176.8 (4)
C12—C5—C6—C11	0.1 (5)	C26—C25—C30—C29	1.6 (5)
C4—C5—C6—C7	1.4 (5)	C22—C25—C30—C29	179.5 (3)
C12—C5—C6—C7	178.0 (3)	C28—C29—C30—C25	0.0 (5)
C11—C6—C7—C8	−3.5 (5)	N3—C29—C30—C25	−177.7 (3)
C5—C6—C7—C8	178.5 (3)	N4—C32—C33—N3	−1.3 (4)
C11—C6—C7—C2	175.3 (3)	N2—C13—N1—C14	0.2 (4)
C5—C6—C7—C2	−2.7 (5)	N2—C13—N1—Ni1	−177.6 (2)
C3—C2—C7—C8	−178.7 (3)	C15—C14—N1—C13	0.0 (4)
C1—C2—C7—C8	0.5 (5)	C15—C14—N1—Ni1	177.5 (3)
C3—C2—C7—C6	2.5 (5)	O1W—Ni1—N1—C13	49.8 (3)
C1—C2—C7—C6	−178.3 (3)	O2—Ni1—N1—C13	−40.3 (3)
C6—C7—C8—C9	1.3 (5)	N4ⁱ—Ni1—N1—C13	142.7 (3)
C2—C7—C8—C9	−177.4 (3)	O3ⁱⁱ—Ni1—N1—C13	−124.9 (3)
C7—C8—C9—C10	1.2 (6)	O4ⁱⁱ—Ni1—N1—C13	−122.6 (4)
C8—C9—C10—C11	−1.3 (6)	C12ⁱⁱ—Ni1—N1—C13	−125.0 (3)
C9—C10—C11—C6	−1.1 (6)	O1W—Ni1—N1—C14	−127.3 (3)
C5—C6—C11—C10	−178.5 (3)	O2—Ni1—N1—C14	142.6 (3)
C7—C6—C11—C10	3.5 (5)	N4ⁱ—Ni1—N1—C14	−34.5 (3)
C4—C5—C12—O3	53.8 (4)	O3ⁱⁱ—Ni1—N1—C14	57.9 (3)
C6—C5—C12—O3	−122.8 (3)	O4ⁱⁱ—Ni1—N1—C14	60.2 (6)
C4—C5—C12—O4	−126.5 (3)	C12ⁱⁱ—Ni1—N1—C14	57.8 (4)
C6—C5—C12—O4	56.9 (4)	N1—C13—N2—C15	−0.4 (4)
C4—C5—C12—Ni1ⁱⁱⁱ	77 (3)	N1—C13—N2—C16	−179.1 (3)
C6—C5—C12—Ni1ⁱⁱⁱ	−100 (3)	C14—C15—N2—C13	0.4 (4)
N1—C14—C15—N2	−0.3 (4)	C14—C15—N2—C16	179.0 (3)
C21—C16—C17—C18	1.0 (6)	C21—C16—N2—C13	−35.6 (5)
N2—C16—C17—C18	−178.3 (3)	C17—C16—N2—C13	143.7 (4)
C16—C17—C18—C19	1.6 (6)	C21—C16—N2—C15	146.0 (4)
C17—C18—C19—C20	−2.2 (6)	C17—C16—N2—C15	−34.7 (6)
C17—C18—C19—C26	174.3 (4)	N4—C31—N3—C33	−0.4 (4)
C18—C19—C20—C21	0.3 (5)	N4—C31—N3—C29	−171.0 (3)
C26—C19—C20—C21	−177.0 (3)	C32—C33—N3—C31	1.0 (4)
C18—C19—C20—C22	−179.8 (3)	C32—C33—N3—C29	171.6 (3)
C26—C19—C20—C22	2.9 (4)	C28—C29—N3—C31	−45.2 (5)
C19—C20—C21—C16	2.3 (5)	C30—C29—N3—C31	132.6 (4)
C22—C20—C21—C16	−177.6 (3)	C28—C29—N3—C33	146.1 (4)
C17—C16—C21—C20	−2.9 (5)	C30—C29—N3—C33	−36.2 (5)
N2—C16—C21—C20	176.4 (3)	N3—C31—N4—C32	−0.4 (4)
C21—C20—C22—C23	56.6 (5)	N3—C31—N4—Ni1^iv	163.9 (2)
C19—C20—C22—C23	−123.3 (3)	C33—C32—N4—C31	1.0 (4)
C21—C20—C22—C24	−67.5 (4)	C33—C32—N4—Ni1^iv	−163.3 (3)
C19—C20—C22—C24	112.6 (3)	O1—C1—O2—Ni1	7.5 (6)
C21—C20—C22—C25	176.2 (3)	C2—C1—O2—Ni1	−169.7 (2)
C19—C20—C22—C25	−3.7 (4)	O1W—Ni1—O2—C1	−8.8 (3)
C20—C22—C25—C30	−174.8 (3)	N1—Ni1—O2—C1	83.7 (3)
C23—C22—C25—C30	−56.0 (5)	N4ⁱ—Ni1—O2—C1	−134.4 (12)
C24—C22—C25—C30	68.0 (4)	O3ⁱⁱ—Ni1—O2—C1	−170.9 (3)
C20—C22—C25—C26	3.3 (4)	O4ⁱⁱ—Ni1—O2—C1	−110.0 (3)
C23—C22—C25—C26	122.0 (3)	C12ⁱⁱ—Ni1—O2—C1	−140.5 (3)
C24—C22—C25—C26	−113.9 (3)	O4—C12—O3—Ni1ⁱⁱⁱ	−1.4 (3)
C30—C25—C26—C27	−2.4 (6)	C5—C12—O3—Ni1ⁱⁱⁱ	178.3 (2)
C22—C25—C26—C27	179.4 (3)	O3—C12—O4—Ni1ⁱⁱⁱ	1.3 (3)
C30—C25—C26—C19	176.4 (3)	C5—C12—O4—Ni1ⁱⁱⁱ	−178.4 (3)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1A···O1	0.85 (1)	1.88 (2)	2.659 (3)	152 (4)
O1W—H1B···O4^v	0.85 (1)	1.94 (1)	2.791 (3)	176 (4)

Symmetry code: (v) x+1/2, −y+1/2, z+1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1A···O1	0.848 (10)	1.88 (2)	2.659 (3)	152 (4)
O1W—H1B···O4ⁱ	0.851 (10)	1.942 (11)	2.791 (3)	176 (4)

Symmetry code: (i) x+1/2, −y+1/2, z+1/2.

Acknowledgements

We thank the Science Foundation of Jilin Province (grant No. 20140101121JC).

References

Brandenburg, K. (2008). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Bruker (2002). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Guo, C.-L., Yao, X.-Q., Cheng, Y.-Q. & Liu, Y. (2013). Acta Cryst. C69, 1022–1025. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Kaduk, J. A. & Hanko, J. A. (2001). J. Appl. Cryst. 34, 710–714. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 70| Part 9| September 2014| Pages m324-m325

doi:10.1107/S1600536814017681

Open

access

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

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

Crystal structure of poly[aqua­[μ-1,1′-(9,9-di­methyl-9H-fluoren-2,7-di­yl)di-1H-imidazole](μ-naphthalene-1,4-di­carboxyl­ato)nickel(II)]

1. Related literature

2. Experimental

2.1. Crystal data

2.2. Data collection

2.3. Refinement

Supporting information

Acknowledgements

References

metal-organic compounds

Crystal structure of poly[aqua[μ-1,1′-(9,9-dimethyl-9H-fluoren-2,7-diyl)di-1H-imidazole](μ-naphthalene-1,4-dicarboxylato)nickel(II)]