(2-Carboxy­benzoato-κ2O1,O1′)(5,5,7,12,12,14-hexa­methyl-1,4,8,11-tetra­azacyclo­tetra­decane-κ4N)nickel(II) perchlorate monohydrate

Ou, G.-C.; Zhang, M.; Yuan, X.-Y.

doi:10.1107/S1600536809020169

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 7| July 2009| Page m726

doi:10.1107/S1600536809020169

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(2-Carboxybenzoato-κ²O¹,O^1′)(5,5,7,12,12,14-hexamethyl-1,4,8,11-tetraazacyclotetradecane-κ⁴N)nickel(II) perchlorate monohydrate

Guang-Chuan Ou,^a ^* Min Zhang ^a and Xian-You Yuan ^a

^aDepartment of Biology and Chemistry, Hunan University of Science and Engineering, Yongzhou Hunan 425100, People's Republic of China
^*Correspondence e-mail: ouguangchuan@yahoo.com.cn

(Received 20 May 2009; accepted 27 May 2009; online 6 June 2009)

The title compound, [Ni(C₈H₅O₄)(C₁₆H₃₆N₄)]ClO₄·H₂O, has the Ni^II atom in a distorted octahedral geometry, surrounded by coordination by four N atoms of the 5,5,7,12,12,14-hexamethyl-1,4,8,11-tetraazacyclotetradecane ligand in a folded configuration, and two carboxylate O atoms of the 2-carboxybenzoate ligand in cis positions. The complex cation, the disordered perchlorate anion [occupancies 0.639 (8):0.361 (8)] and uncoordinated water molecules engage in N—H⋯O and O—H⋯O hydrogen bonding, forming a layer structure parallel to (010).

Related literature

For background literature, see: Tait & Busch (1976 ); Curtis (1965 ). For related crystal structures, see: Zeigerson et al. (1982 ); Gao et al. (2002 ); Burrows et al. (2004 ); Ou et al. (2008 ). For a discussion of helical coordination polymers, see: Khatua et al. (2006 ); Lonnon et al. (2006 ); Telfer & Kuroda (2005 ).

Experimental

Crystal data

[Ni(C₈H₅O₄)(C₁₆H₃₆N₄)]ClO₄·H₂O
M_r = 625.78
Monoclinic, P 2₁ /c
a = 9.7941 (12) Å
b = 17.354 (2) Å
c = 17.619 (2) Å
β = 102.105 (2)°
V = 2928.2 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.81 mm⁻¹
T = 173 K
0.46 × 0.41 × 0.18 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.707, T_max = 0.868
14639 measured reflections
6322 independent reflections
4597 reflections with I > 2σ(I)
R_int = 0.030

Refinement

R[F² > 2σ(F²)] = 0.048
wR(F²) = 0.151
S = 1.07
6322 reflections
411 parameters
47 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.77 e Å⁻³
Δρ_min = −0.42 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1C⋯O5ⁱ	0.93	2.29	3.094 (9)	144
N2—H2C⋯O6′ⁱⁱ	0.93	2.03	2.952 (10)	173
O4—H4⋯O1W	0.84	1.76	2.572 (4)	162
O1W—H2W⋯O8	0.855 (11)	2.13 (3)	2.827 (5)	138 (4)
O1W—H1W⋯O1ⁱⁱⁱ	0.860 (11)	1.892 (16)	2.734 (3)	166 (4)
Symmetry codes: (i) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (ii) -x+1, -y, -z; (iii) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 1999 ); cell refinement: SAINT-Plus (Bruker, 1999); data reduction: SAINT-Plus; 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/S1600536809020169/ng2586sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809020169/ng2586Isup2.hkl

checkCIF report

Comment top

Recently, many helical structures were constructed through the coordination interactions, and helical polymers constructed via hydrogen bonding are still rare, and only a few cases have been reported (Khatua et al., 2006; Lonnon et al., 2006; Telfer & Kuroda, 2005). Then we employ racemic nickel(II) complex and phthalic acid as building blocks to construct helical structure, but the result of experiment indicate a racemic complex of [Ni(rac-L)(Hpt)(ClO₄)]^.H₂O (pt=phthalic acid) is obtained.

In the asymmetric unit of (I), contains one [Ni(rac-L)(Hpt)]⁺ cation, one [ClO₄]^- anion and one water molecule. The [ClO₄]^- anion is disordered over two symmetry related sites with 50% occupancy. As illustrated in Fig.1, The six-coordinated Ni²⁺ of [Ni(rac-L)(Hpt)]⁺ cation displays a distorted octahedral geometry by coordination with four N atoms of macrocyclic ligand L in a folded configuration, and two carboxylate oxygen atoms of phthalic acid in cis-position. Neighbouring cations, anions and water molecule are discrete, connected to each other through intermolecular hydrogen bond.

Related literature top

For background literature, see: Tait et al. (1976); Curtis (1965). For related crystal structures, see: Zeigerson et al. (1982); Gao et al. (2002); Burrows et al. (2004); Ou et al. (2008). For a discussion of helical coordination polymers, see: Khatua et al. (2006); Lonnon et al. (2006); Telfer & Kuroda (2005).

Experimental top

Phthalic acid (H₂pt, 0.166 g, 1 mmol) was mixed with NaOH (0.040 g, 1 mmol) dissolved in 10 ml of water. To this solution was added [Ni(rac-L)](ClO₄)₂ (0.541 g, 1 mmol) dissolved in a minimum amount of CH₃CN. The solution was left to stand at room temperature and blue crystals formed after several weeks.

Computing details top

Data collection: SMART (Bruker, 1999); cell refinement: SAINT-Plus (Bruker, 1999); data reduction: SAINT-Plus (Bruker, 1999); 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 molecular structure of (I), showing displacement ellipsoids at the 30% probability level. H-atoms have been excluded for clarity.
	Fig. 2. A view of the packing of the title compound.

(2-Carboxybenzoato-κ²O¹,O^1')(5,5,7,12,12,14-hexamethyl- 1,4,8,11-tetraazacyclotetradecane-κ⁴N)nickel(II) perchlorate monohydrate top

Crystal data top

[Ni(C₈H₅O₄)(C₁₆H₃₆N₄)]ClO₄·H₂O	F(000) = 1328
M_r = 625.78	D_x = 1.420 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 9.7941 (12) Å	Cell parameters from 5283 reflections
b = 17.354 (2) Å	θ = 2.4–27.0°
c = 17.619 (2) Å	µ = 0.81 mm⁻¹
β = 102.105 (2)°	T = 173 K
V = 2928.2 (6) Å³	Block, blue
Z = 4	0.46 × 0.41 × 0.18 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	6322 independent reflections
Radiation source: fine-focus sealed tube	4597 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.030
ϕ and ω scans	θ_max = 27.1°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→11
T_min = 0.707, T_max = 0.868	k = −22→17
14639 measured reflections	l = −22→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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.151	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ²(F_o²) + (0.0858P)² + 1.13P] where P = (F_o² + 2F_c²)/3
6322 reflections	(Δ/σ)_max < 0.001
411 parameters	Δρ_max = 0.77 e Å⁻³
47 restraints	Δρ_min = −0.42 e Å⁻³

Crystal data top

[Ni(C₈H₅O₄)(C₁₆H₃₆N₄)]ClO₄·H₂O	V = 2928.2 (6) Å³
M_r = 625.78	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 9.7941 (12) Å	µ = 0.81 mm⁻¹
b = 17.354 (2) Å	T = 173 K
c = 17.619 (2) Å	0.46 × 0.41 × 0.18 mm
β = 102.105 (2)°

Data collection top

Bruker SMART CCD area-detector diffractometer	6322 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	4597 reflections with I > 2σ(I)
T_min = 0.707, T_max = 0.868	R_int = 0.030
14639 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	47 restraints
wR(F²) = 0.151	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	Δρ_max = 0.77 e Å⁻³
6322 reflections	Δρ_min = −0.42 e Å⁻³
411 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	Occ. (<1)
Ni1	0.32081 (4)	0.21532 (2)	0.13185 (2)	0.02393 (14)
O1	0.1559 (2)	0.29722 (12)	0.13918 (12)	0.0279 (5)
O2	0.2165 (2)	0.27282 (12)	0.02880 (13)	0.0277 (5)
N1	0.4733 (3)	0.30047 (15)	0.17667 (16)	0.0292 (6)
H1C	0.4229	0.3432	0.1871	0.035*
O3	−0.0163 (3)	0.18524 (14)	−0.05475 (14)	0.0379 (6)
N3	0.1821 (3)	0.12179 (15)	0.09356 (16)	0.0307 (6)
H3A	0.1206	0.1395	0.0495	0.037*
N4	0.4586 (3)	0.15922 (15)	0.07460 (16)	0.0291 (6)
H4D	0.5215	0.1309	0.1109	0.035*
C17	0.1329 (3)	0.30254 (17)	0.06606 (19)	0.0257 (7)
C18	0.0067 (3)	0.34386 (17)	0.02248 (18)	0.0251 (6)
N2	0.3653 (3)	0.17186 (16)	0.24485 (16)	0.0313 (6)
H2C	0.4281	0.1314	0.2465	0.038*
C23	−0.0603 (3)	0.32076 (19)	−0.05238 (19)	0.0282 (7)
O4	−0.0144 (3)	0.25603 (16)	−0.15998 (15)	0.0474 (7)
H4	0.0042	0.2136	−0.1784	0.071*
C11	0.5392 (4)	0.2112 (2)	0.0331 (2)	0.0342 (8)
H11	0.4714	0.2448	−0.0025	0.041*
C24	−0.0246 (3)	0.2465 (2)	−0.08727 (19)	0.0306 (7)
C3	0.2428 (4)	0.1426 (2)	0.2747 (2)	0.0381 (8)
H3	0.1712	0.1845	0.2687	0.046*
C1	0.5447 (4)	0.2708 (2)	0.2534 (2)	0.0387 (8)
H1A	0.5936	0.3134	0.2854	0.046*
H1B	0.6150	0.2317	0.2468	0.046*
C2	0.4381 (4)	0.2353 (2)	0.2933 (2)	0.0395 (9)
H2A	0.4850	0.2150	0.3447	0.047*
H2B	0.3697	0.2748	0.3013	0.047*
C22	−0.1695 (4)	0.3647 (2)	−0.0938 (2)	0.0392 (8)
H22	−0.2133	0.3500	−0.1451	0.047*
C9	0.2719 (4)	0.0646 (2)	0.0655 (2)	0.0399 (8)
H9A	0.2131	0.0271	0.0308	0.048*
H9B	0.3274	0.0360	0.1101	0.048*
C13	0.6348 (4)	0.2627 (2)	0.0907 (2)	0.0358 (8)
H13A	0.7054	0.2845	0.0639	0.043*
H13B	0.6854	0.2294	0.1330	0.043*
C19	−0.0391 (4)	0.40969 (19)	0.0544 (2)	0.0337 (8)
H19	0.0059	0.4259	0.1050	0.040*
C14	0.5715 (4)	0.3301 (2)	0.1285 (2)	0.0355 (8)
C4	0.2814 (6)	0.1203 (3)	0.3605 (2)	0.0602 (12)
H4A	0.3532	0.0800	0.3679	0.090*
H4B	0.1983	0.1009	0.3771	0.090*
H4C	0.3174	0.1655	0.3916	0.090*
C7	−0.0259 (4)	0.1456 (2)	0.1469 (2)	0.0433 (9)
H7A	0.0142	0.1958	0.1648	0.065*
H7B	−0.0835	0.1270	0.1823	0.065*
H7C	−0.0837	0.1509	0.0946	0.065*
C20	−0.1508 (4)	0.4520 (2)	0.0127 (2)	0.0415 (9)
H20	−0.1829	0.4964	0.0353	0.050*
C10	0.3674 (4)	0.1046 (2)	0.0226 (2)	0.0363 (8)
H10A	0.4255	0.0662	0.0024	0.044*
H10B	0.3117	0.1329	−0.0222	0.044*
C15	0.4879 (4)	0.3840 (2)	0.0673 (2)	0.0425 (9)
H15A	0.4044	0.3572	0.0392	0.064*
H15B	0.5457	0.3994	0.0307	0.064*
H15C	0.4601	0.4299	0.0928	0.064*
C21	−0.2147 (4)	0.4296 (2)	−0.0612 (2)	0.0446 (9)
H21	−0.2901	0.4590	−0.0898	0.053*
C5	0.1784 (4)	0.0737 (2)	0.2264 (2)	0.0419 (9)
H5A	0.2552	0.0383	0.2213	0.050*
H5B	0.1186	0.0460	0.2564	0.050*
C6	0.0915 (4)	0.0883 (2)	0.1453 (2)	0.0378 (8)
C16	0.6912 (4)	0.3766 (3)	0.1778 (3)	0.0499 (10)
H16A	0.6527	0.4155	0.2078	0.075*
H16B	0.7446	0.4020	0.1438	0.075*
H16C	0.7527	0.3419	0.2134	0.075*
C12	0.6241 (4)	0.1662 (3)	−0.0161 (2)	0.0482 (10)
H12A	0.6838	0.1286	0.0168	0.072*
H12B	0.6823	0.2020	−0.0384	0.072*
H12C	0.5603	0.1392	−0.0579	0.072*
C8	0.0254 (5)	0.0123 (2)	0.1121 (3)	0.0574 (12)
H8A	−0.0166	0.0190	0.0569	0.086*
H8B	−0.0470	−0.0030	0.1400	0.086*
H8C	0.0973	−0.0278	0.1181	0.086*
O1W	0.0544 (3)	0.14387 (16)	−0.23970 (16)	0.0481 (7)
H2W	0.118 (3)	0.111 (2)	−0.221 (2)	0.058*
H1W	0.072 (4)	0.161 (2)	−0.2823 (14)	0.058*
Cl1	0.3438 (6)	−0.0040 (3)	−0.2176 (3)	0.0381 (10)	0.639 (8)
Cl1'	0.3673 (10)	0.0103 (6)	−0.2158 (6)	0.0362 (18)	0.361 (8)
O5	0.4344 (13)	0.0455 (7)	−0.2420 (9)	0.203 (6)	0.639 (8)
O6	0.3623 (8)	−0.0075 (5)	−0.1357 (3)	0.110 (3)	0.639 (8)
O7	0.3697 (8)	−0.0818 (3)	−0.2264 (4)	0.073 (2)	0.639 (8)
O8	0.2001 (5)	0.0061 (3)	−0.2550 (3)	0.0588 (18)	0.639 (8)
O5'	0.2976 (14)	0.0479 (5)	−0.2866 (5)	0.088 (5)	0.361 (8)
O6'	0.4169 (15)	−0.0535 (8)	−0.2485 (9)	0.101 (5)	0.361 (8)
O7'	0.4898 (15)	0.0527 (8)	−0.1817 (8)	0.152 (8)	0.361 (8)
O8'	0.2850 (14)	0.0248 (7)	−0.1601 (7)	0.098 (4)	0.361 (8)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ni1	0.0271 (2)	0.0244 (2)	0.0195 (2)	0.00258 (16)	0.00305 (15)	−0.00112 (15)
O1	0.0295 (12)	0.0330 (12)	0.0216 (11)	0.0013 (9)	0.0061 (9)	0.0000 (9)
O2	0.0262 (12)	0.0310 (11)	0.0264 (12)	0.0036 (9)	0.0067 (9)	0.0019 (9)
N1	0.0267 (14)	0.0304 (14)	0.0297 (15)	0.0014 (11)	0.0040 (11)	−0.0041 (11)
O3	0.0481 (15)	0.0336 (12)	0.0308 (13)	−0.0032 (11)	0.0052 (11)	0.0010 (11)
N3	0.0349 (16)	0.0295 (14)	0.0276 (14)	−0.0039 (12)	0.0066 (12)	0.0000 (11)
N4	0.0297 (15)	0.0295 (13)	0.0263 (14)	0.0020 (11)	0.0013 (11)	−0.0028 (11)
C17	0.0266 (16)	0.0248 (15)	0.0257 (16)	−0.0030 (13)	0.0056 (13)	−0.0008 (12)
C18	0.0275 (16)	0.0261 (15)	0.0240 (15)	0.0011 (13)	0.0107 (13)	0.0055 (12)
N2	0.0353 (16)	0.0343 (15)	0.0246 (14)	0.0051 (12)	0.0072 (12)	0.0018 (12)
C23	0.0266 (17)	0.0320 (16)	0.0270 (16)	0.0019 (13)	0.0075 (13)	0.0052 (13)
O4	0.070 (2)	0.0463 (15)	0.0302 (14)	0.0120 (14)	0.0210 (13)	0.0026 (12)
C11	0.0335 (19)	0.0417 (19)	0.0280 (17)	0.0011 (15)	0.0082 (14)	−0.0003 (15)
C24	0.0273 (17)	0.0380 (18)	0.0255 (17)	0.0003 (14)	0.0031 (13)	0.0011 (14)
C3	0.046 (2)	0.0404 (19)	0.0307 (18)	0.0032 (16)	0.0146 (16)	0.0054 (15)
C1	0.038 (2)	0.046 (2)	0.0284 (18)	0.0028 (17)	0.0008 (15)	−0.0055 (15)
C2	0.048 (2)	0.044 (2)	0.0223 (17)	0.0004 (17)	−0.0005 (15)	−0.0046 (15)
C22	0.037 (2)	0.047 (2)	0.0315 (19)	0.0065 (17)	0.0015 (15)	0.0058 (16)
C9	0.047 (2)	0.0314 (17)	0.041 (2)	−0.0025 (16)	0.0076 (17)	−0.0084 (15)
C13	0.0241 (17)	0.0445 (19)	0.040 (2)	−0.0014 (15)	0.0104 (15)	−0.0005 (16)
C19	0.040 (2)	0.0340 (17)	0.0293 (18)	0.0055 (15)	0.0119 (15)	0.0038 (14)
C14	0.0290 (18)	0.0378 (19)	0.040 (2)	−0.0038 (15)	0.0074 (15)	−0.0027 (15)
C4	0.083 (3)	0.066 (3)	0.032 (2)	−0.004 (2)	0.011 (2)	0.011 (2)
C7	0.038 (2)	0.051 (2)	0.043 (2)	−0.0073 (17)	0.0136 (17)	0.0032 (18)
C20	0.045 (2)	0.041 (2)	0.043 (2)	0.0164 (17)	0.0174 (17)	0.0065 (17)
C10	0.039 (2)	0.0370 (18)	0.0336 (19)	0.0012 (15)	0.0087 (15)	−0.0113 (15)
C15	0.045 (2)	0.0372 (19)	0.046 (2)	−0.0041 (17)	0.0120 (18)	0.0066 (17)
C21	0.038 (2)	0.052 (2)	0.043 (2)	0.0179 (18)	0.0095 (17)	0.0129 (18)
C5	0.058 (3)	0.0343 (18)	0.036 (2)	−0.0039 (17)	0.0169 (18)	0.0123 (16)
C6	0.046 (2)	0.0337 (18)	0.0355 (19)	−0.0096 (16)	0.0123 (16)	0.0036 (15)
C16	0.037 (2)	0.057 (2)	0.055 (3)	−0.0129 (19)	0.0075 (18)	−0.009 (2)
C12	0.043 (2)	0.066 (3)	0.039 (2)	−0.003 (2)	0.0167 (18)	−0.0105 (19)
C8	0.067 (3)	0.049 (2)	0.062 (3)	−0.026 (2)	0.027 (2)	−0.007 (2)
O1W	0.069 (2)	0.0448 (16)	0.0372 (15)	0.0128 (14)	0.0273 (14)	0.0081 (12)
Cl1	0.0404 (19)	0.0348 (18)	0.0393 (12)	0.0025 (14)	0.0087 (11)	0.0016 (10)
Cl1'	0.035 (3)	0.034 (3)	0.040 (2)	0.005 (3)	0.0083 (19)	0.006 (2)
O5	0.180 (9)	0.197 (9)	0.234 (10)	−0.089 (7)	0.044 (8)	0.110 (8)
O6	0.092 (5)	0.180 (7)	0.054 (4)	0.050 (5)	0.010 (3)	−0.003 (4)
O7	0.068 (5)	0.056 (4)	0.086 (5)	0.017 (3)	−0.006 (3)	0.009 (3)
O8	0.045 (3)	0.063 (3)	0.063 (3)	0.016 (2)	0.000 (2)	−0.012 (3)
O5'	0.124 (11)	0.046 (5)	0.069 (7)	0.021 (6)	−0.040 (7)	0.004 (5)
O6'	0.085 (8)	0.090 (8)	0.109 (9)	0.056 (7)	−0.025 (6)	−0.050 (7)
O7'	0.27 (2)	0.110 (11)	0.073 (9)	−0.111 (13)	0.018 (11)	−0.030 (8)
O8'	0.121 (9)	0.099 (7)	0.080 (7)	0.041 (6)	0.033 (7)	−0.005 (6)

Geometric parameters (Å, º) top

Ni1—N4	2.087 (3)	C13—C14	1.539 (5)
Ni1—N2	2.088 (3)	C13—H13A	0.9900
Ni1—N1	2.131 (3)	C13—H13B	0.9900
Ni1—N3	2.133 (3)	C19—C20	1.393 (5)
Ni1—O2	2.135 (2)	C19—H19	0.9500
Ni1—O1	2.176 (2)	C14—C15	1.529 (5)
Ni1—C17	2.475 (3)	C14—C16	1.533 (5)
O1—C17	1.264 (4)	C4—H4A	0.9800
O2—C17	1.262 (4)	C4—H4B	0.9800
N1—C1	1.478 (4)	C4—H4C	0.9800
N1—C14	1.501 (4)	C7—C6	1.524 (5)
N1—H1C	0.9300	C7—H7A	0.9800
O3—C24	1.202 (4)	C7—H7B	0.9800
N3—C9	1.479 (4)	C7—H7C	0.9800
N3—C6	1.516 (4)	C20—C21	1.378 (6)
N3—H3A	0.9300	C20—H20	0.9500
N4—C10	1.480 (4)	C10—H10A	0.9900
N4—C11	1.488 (4)	C10—H10B	0.9900
N4—H4D	0.9300	C15—H15A	0.9800
C17—C18	1.495 (4)	C15—H15B	0.9800
C18—C19	1.389 (4)	C15—H15C	0.9800
C18—C23	1.403 (4)	C21—H21	0.9500
N2—C2	1.481 (4)	C5—C6	1.523 (5)
N2—C3	1.496 (4)	C5—H5A	0.9900
N2—H2C	0.9300	C5—H5B	0.9900
C23—C22	1.389 (5)	C6—C8	1.531 (5)
C23—C24	1.501 (5)	C16—H16A	0.9800
O4—C24	1.316 (4)	C16—H16B	0.9800
O4—H4	0.8400	C16—H16C	0.9800
C11—C13	1.520 (5)	C12—H12A	0.9800
C11—C12	1.534 (5)	C12—H12B	0.9800
C11—H11	1.0000	C12—H12C	0.9800
C3—C5	1.527 (5)	C8—H8A	0.9800
C3—C4	1.530 (5)	C8—H8B	0.9800
C3—H3	1.0000	C8—H8C	0.9800
C1—C2	1.508 (5)	O1W—H2W	0.855 (11)
C1—H1A	0.9900	O1W—H1W	0.860 (11)
C1—H1B	0.9900	Cl1—O5	1.367 (7)
C2—H2A	0.9900	Cl1—O7	1.390 (7)
C2—H2B	0.9900	Cl1—O6	1.418 (7)
C22—C21	1.379 (5)	Cl1—O8	1.434 (6)
C22—H22	0.9500	Cl1'—O6'	1.383 (9)
C9—C10	1.492 (5)	Cl1'—O8'	1.416 (9)
C9—H9A	0.9900	Cl1'—O7'	1.428 (9)
C9—H9B	0.9900	Cl1'—O5'	1.446 (9)

N4—Ni1—N2	105.40 (11)	C10—C9—H9A	109.7
N4—Ni1—N1	91.66 (10)	N3—C9—H9B	109.7
N2—Ni1—N1	84.67 (11)	C10—C9—H9B	109.7
N4—Ni1—N3	85.73 (11)	H9A—C9—H9B	108.2
N2—Ni1—N3	91.06 (11)	C11—C13—C14	119.2 (3)
N1—Ni1—N3	174.23 (11)	C11—C13—H13A	107.5
N4—Ni1—O2	92.84 (10)	C14—C13—H13A	107.5
N2—Ni1—O2	161.23 (10)	C11—C13—H13B	107.5
N1—Ni1—O2	99.45 (10)	C14—C13—H13B	107.5
N3—Ni1—O2	85.83 (10)	H13A—C13—H13B	107.0
N4—Ni1—O1	153.72 (10)	C18—C19—C20	120.3 (3)
N2—Ni1—O1	100.86 (10)	C18—C19—H19	119.8
N1—Ni1—O1	89.79 (10)	C20—C19—H19	119.8
N3—Ni1—O1	94.84 (10)	N1—C14—C15	107.2 (3)
O2—Ni1—O1	61.07 (8)	N1—C14—C16	111.4 (3)
N4—Ni1—C17	123.46 (11)	C15—C14—C16	108.1 (3)
N2—Ni1—C17	130.81 (11)	N1—C14—C13	110.4 (3)
N1—Ni1—C17	98.26 (10)	C15—C14—C13	111.4 (3)
N3—Ni1—C17	87.46 (10)	C16—C14—C13	108.4 (3)
O2—Ni1—C17	30.65 (9)	C3—C4—H4A	109.5
O1—Ni1—C17	30.68 (9)	C3—C4—H4B	109.5
C17—O1—Ni1	87.86 (18)	H4A—C4—H4B	109.5
C17—O2—Ni1	89.74 (19)	C3—C4—H4C	109.5
C1—N1—C14	113.5 (3)	H4A—C4—H4C	109.5
C1—N1—Ni1	104.9 (2)	H4B—C4—H4C	109.5
C14—N1—Ni1	120.7 (2)	C6—C7—H7A	109.5
C1—N1—H1C	105.5	C6—C7—H7B	109.5
C14—N1—H1C	105.5	H7A—C7—H7B	109.5
Ni1—N1—H1C	105.5	C6—C7—H7C	109.5
C9—N3—C6	114.1 (3)	H7A—C7—H7C	109.5
C9—N3—Ni1	103.5 (2)	H7B—C7—H7C	109.5
C6—N3—Ni1	121.1 (2)	C21—C20—C19	120.1 (3)
C9—N3—H3A	105.7	C21—C20—H20	120.0
C6—N3—H3A	105.7	C19—C20—H20	120.0
Ni1—N3—H3A	105.7	N4—C10—C9	110.2 (3)
C10—N4—C11	113.4 (3)	N4—C10—H10A	109.6
C10—N4—Ni1	103.3 (2)	C9—C10—H10A	109.6
C11—N4—Ni1	114.7 (2)	N4—C10—H10B	109.6
C10—N4—H4D	108.4	C9—C10—H10B	109.6
C11—N4—H4D	108.4	H10A—C10—H10B	108.1
Ni1—N4—H4D	108.4	C14—C15—H15A	109.5
O2—C17—O1	120.3 (3)	C14—C15—H15B	109.5
O2—C17—C18	119.1 (3)	H15A—C15—H15B	109.5
O1—C17—C18	120.6 (3)	C14—C15—H15C	109.5
O2—C17—Ni1	59.61 (16)	H15A—C15—H15C	109.5
O1—C17—Ni1	61.46 (16)	H15B—C15—H15C	109.5
C18—C17—Ni1	171.0 (2)	C20—C21—C22	120.2 (3)
C19—C18—C23	119.3 (3)	C20—C21—H21	119.9
C19—C18—C17	119.3 (3)	C22—C21—H21	119.9
C23—C18—C17	121.3 (3)	C6—C5—C3	118.4 (3)
C2—N2—C3	112.0 (3)	C6—C5—H5A	107.7
C2—N2—Ni1	105.1 (2)	C3—C5—H5A	107.7
C3—N2—Ni1	115.8 (2)	C6—C5—H5B	107.7
C2—N2—H2C	107.9	C3—C5—H5B	107.7
C3—N2—H2C	107.9	H5A—C5—H5B	107.1
Ni1—N2—H2C	107.9	N3—C6—C5	110.2 (3)
C22—C23—C18	119.6 (3)	N3—C6—C7	107.5 (3)
C22—C23—C24	118.4 (3)	C5—C6—C7	111.5 (3)
C18—C23—C24	121.8 (3)	N3—C6—C8	110.7 (3)
C24—O4—H4	109.5	C5—C6—C8	108.9 (3)
N4—C11—C13	110.2 (3)	C7—C6—C8	108.0 (3)
N4—C11—C12	112.0 (3)	C14—C16—H16A	109.5
C13—C11—C12	110.2 (3)	C14—C16—H16B	109.5
N4—C11—H11	108.1	H16A—C16—H16B	109.5
C13—C11—H11	108.1	C14—C16—H16C	109.5
C12—C11—H11	108.1	H16A—C16—H16C	109.5
O3—C24—O4	124.3 (3)	H16B—C16—H16C	109.5
O3—C24—C23	124.2 (3)	C11—C12—H12A	109.5
O4—C24—C23	111.3 (3)	C11—C12—H12B	109.5
N2—C3—C5	109.8 (3)	H12A—C12—H12B	109.5
N2—C3—C4	112.5 (3)	C11—C12—H12C	109.5
C5—C3—C4	109.8 (3)	H12A—C12—H12C	109.5
N2—C3—H3	108.2	H12B—C12—H12C	109.5
C5—C3—H3	108.2	C6—C8—H8A	109.5
C4—C3—H3	108.2	C6—C8—H8B	109.5
N1—C1—C2	109.1 (3)	H8A—C8—H8B	109.5
N1—C1—H1A	109.9	C6—C8—H8C	109.5
C2—C1—H1A	109.9	H8A—C8—H8C	109.5
N1—C1—H1B	109.9	H8B—C8—H8C	109.5
C2—C1—H1B	109.9	H2W—O1W—H1W	108.1 (17)
H1A—C1—H1B	108.3	O5—Cl1—O7	115.5 (8)
N2—C2—C1	109.4 (3)	O5—Cl1—O6	113.2 (8)
N2—C2—H2A	109.8	O7—Cl1—O6	94.8 (6)
C1—C2—H2A	109.8	O5—Cl1—O8	114.8 (7)
N2—C2—H2B	109.8	O7—Cl1—O8	104.5 (5)
C1—C2—H2B	109.8	O6—Cl1—O8	112.1 (6)
H2A—C2—H2B	108.2	O6'—Cl1'—O8'	137.0 (11)
C21—C22—C23	120.5 (3)	O6'—Cl1'—O7'	104.5 (10)
C21—C22—H22	119.7	O8'—Cl1'—O7'	99.6 (9)
C23—C22—H22	119.7	O6'—Cl1'—O5'	98.4 (9)
N3—C9—C10	109.7 (3)	O8'—Cl1'—O5'	106.4 (9)
N3—C9—H9A	109.7	O7'—Cl1'—O5'	109.5 (9)

N4—Ni1—O1—C17	13.4 (3)	O1—C17—C18—C23	−147.6 (3)
N2—Ni1—O1—C17	−168.73 (18)	Ni1—C17—C18—C23	−46.7 (16)
N1—Ni1—O1—C17	106.74 (19)	N4—Ni1—N2—C2	107.1 (2)
N3—Ni1—O1—C17	−76.71 (19)	N1—Ni1—N2—C2	16.9 (2)
O2—Ni1—O1—C17	5.81 (17)	N3—Ni1—N2—C2	−167.0 (2)
N4—Ni1—O2—C17	177.56 (18)	O2—Ni1—N2—C2	−86.9 (4)
N2—Ni1—O2—C17	11.1 (4)	O1—Ni1—N2—C2	−71.9 (2)
N1—Ni1—O2—C17	−90.29 (19)	C17—Ni1—N2—C2	−79.5 (3)
N3—Ni1—O2—C17	92.06 (19)	N4—Ni1—N2—C3	−128.8 (2)
O1—Ni1—O2—C17	−5.81 (17)	N1—Ni1—N2—C3	141.0 (2)
N4—Ni1—N1—C1	−92.5 (2)	N3—Ni1—N2—C3	−42.9 (2)
N2—Ni1—N1—C1	12.8 (2)	O2—Ni1—N2—C3	37.2 (4)
N3—Ni1—N1—C1	−29.6 (12)	O1—Ni1—N2—C3	52.2 (2)
O2—Ni1—N1—C1	174.4 (2)	C17—Ni1—N2—C3	44.6 (3)
O1—Ni1—N1—C1	113.8 (2)	C19—C18—C23—C22	1.2 (5)
C17—Ni1—N1—C1	143.4 (2)	C17—C18—C23—C22	−174.2 (3)
N4—Ni1—N1—C14	37.3 (2)	C19—C18—C23—C24	−174.3 (3)
N2—Ni1—N1—C14	142.6 (2)	C17—C18—C23—C24	10.3 (5)
N3—Ni1—N1—C14	100.2 (11)	C10—N4—C11—C13	−177.4 (3)
O2—Ni1—N1—C14	−55.9 (2)	Ni1—N4—C11—C13	64.2 (3)
O1—Ni1—N1—C14	−116.5 (2)	C10—N4—C11—C12	−54.3 (4)
C17—Ni1—N1—C14	−86.9 (2)	Ni1—N4—C11—C12	−172.7 (2)
N4—Ni1—N3—C9	12.3 (2)	C22—C23—C24—O3	−126.8 (4)
N2—Ni1—N3—C9	−93.1 (2)	C18—C23—C24—O3	48.7 (5)
N1—Ni1—N3—C9	−50.9 (11)	C22—C23—C24—O4	48.2 (4)
O2—Ni1—N3—C9	105.5 (2)	C18—C23—C24—O4	−136.3 (3)
O1—Ni1—N3—C9	165.9 (2)	C2—N2—C3—C5	−175.8 (3)
C17—Ni1—N3—C9	136.1 (2)	Ni1—N2—C3—C5	63.8 (3)
N4—Ni1—N3—C6	141.7 (3)	C2—N2—C3—C4	−53.1 (4)
N2—Ni1—N3—C6	36.3 (3)	Ni1—N2—C3—C4	−173.6 (3)
N1—Ni1—N3—C6	78.5 (11)	C14—N1—C1—C2	−174.3 (3)
O2—Ni1—N3—C6	−125.2 (2)	Ni1—N1—C1—C2	−40.4 (3)
O1—Ni1—N3—C6	−64.7 (2)	C3—N2—C2—C1	−170.7 (3)
C17—Ni1—N3—C6	−94.5 (3)	Ni1—N2—C2—C1	−44.2 (3)
N2—Ni1—N4—C10	107.1 (2)	N1—C1—C2—N2	59.3 (4)
N1—Ni1—N4—C10	−167.9 (2)	C18—C23—C22—C21	−1.7 (5)
N3—Ni1—N4—C10	17.2 (2)	C24—C23—C22—C21	174.0 (3)
O2—Ni1—N4—C10	−68.4 (2)	C6—N3—C9—C10	−173.9 (3)
O1—Ni1—N4—C10	−75.1 (3)	Ni1—N3—C9—C10	−40.4 (3)
C17—Ni1—N4—C10	−66.9 (2)	N4—C11—C13—C14	−74.1 (4)
N2—Ni1—N4—C11	−128.9 (2)	C12—C11—C13—C14	161.7 (3)
N1—Ni1—N4—C11	−44.0 (2)	C23—C18—C19—C20	0.3 (5)
N3—Ni1—N4—C11	141.1 (2)	C17—C18—C19—C20	175.7 (3)
O2—Ni1—N4—C11	55.5 (2)	C1—N1—C14—C15	−159.6 (3)
O1—Ni1—N4—C11	48.9 (3)	Ni1—N1—C14—C15	74.6 (3)
C17—Ni1—N4—C11	57.0 (2)	C1—N1—C14—C16	−41.5 (4)
Ni1—O2—C17—O1	10.2 (3)	Ni1—N1—C14—C16	−167.3 (2)
Ni1—O2—C17—C18	−169.7 (2)	C1—N1—C14—C13	79.0 (3)
Ni1—O1—C17—O2	−10.0 (3)	Ni1—N1—C14—C13	−46.9 (3)
Ni1—O1—C17—C18	169.9 (3)	C11—C13—C14—N1	62.9 (4)
N4—Ni1—C17—O2	−2.9 (2)	C11—C13—C14—C15	−56.1 (4)
N2—Ni1—C17—O2	−175.31 (17)	C11—C13—C14—C16	−174.9 (3)
N1—Ni1—C17—O2	94.60 (18)	C18—C19—C20—C21	−1.3 (6)
N3—Ni1—C17—O2	−86.11 (18)	C11—N4—C10—C9	−169.9 (3)
O1—Ni1—C17—O2	170.0 (3)	Ni1—N4—C10—C9	−45.1 (3)
N4—Ni1—C17—O1	−172.92 (16)	N3—C9—C10—N4	61.0 (4)
N2—Ni1—C17—O1	14.7 (2)	C19—C20—C21—C22	0.7 (6)
N1—Ni1—C17—O1	−75.39 (18)	C23—C22—C21—C20	0.8 (6)
N3—Ni1—C17—O1	103.90 (18)	N2—C3—C5—C6	−74.9 (4)
O2—Ni1—C17—O1	−170.0 (3)	C4—C3—C5—C6	160.9 (4)
N4—Ni1—C17—C18	81.2 (15)	C9—N3—C6—C5	76.9 (4)
N2—Ni1—C17—C18	−91.2 (14)	Ni1—N3—C6—C5	−47.7 (4)
N1—Ni1—C17—C18	179 (100)	C9—N3—C6—C7	−161.4 (3)
N3—Ni1—C17—C18	−2.0 (14)	Ni1—N3—C6—C7	74.1 (3)
O2—Ni1—C17—C18	84.1 (14)	C9—N3—C6—C8	−43.6 (4)
O1—Ni1—C17—C18	−105.9 (15)	Ni1—N3—C6—C8	−168.2 (3)
O2—C17—C18—C19	−143.1 (3)	C3—C5—C6—N3	64.5 (4)
O1—C17—C18—C19	37.1 (4)	C3—C5—C6—C7	−54.8 (4)
Ni1—C17—C18—C19	138.0 (13)	C3—C5—C6—C8	−173.9 (3)
O2—C17—C18—C23	32.3 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1C···O5ⁱ	0.93	2.29	3.094 (9)	144
N2—H2C···O6′ⁱⁱ	0.93	2.03	2.952 (10)	173
O4—H4···O1W	0.84	1.76	2.572 (4)	162
O1W—H2W···O8	0.86 (1)	2.13 (3)	2.827 (5)	138 (4)
O1W—H1W···O1ⁱⁱⁱ	0.86 (1)	1.89 (2)	2.734 (3)	166 (4)

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

Experimental details

Crystal data
Chemical formula	[Ni(C₈H₅O₄)(C₁₆H₃₆N₄)]ClO₄·H₂O
M_r	625.78
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	173
a, b, c (Å)	9.7941 (12), 17.354 (2), 17.619 (2)
β (°)	102.105 (2)
V (Å³)	2928.2 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.81
Crystal size (mm)	0.46 × 0.41 × 0.18

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.707, 0.868
No. of measured, independent and observed [I > 2σ(I)] reflections	14639, 6322, 4597
R_int	0.030
(sin θ/λ)_max (Å⁻¹)	0.640

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.151, 1.07
No. of reflections	6322
No. of parameters	411
No. of restraints	47
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.77, −0.42

Computer programs: SMART (Bruker, 1999), SAINT-Plus (Bruker, 1999), 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
N1—H1C···O5ⁱ	0.93	2.29	3.094 (9)	144.4
N2—H2C···O6'ⁱⁱ	0.93	2.03	2.952 (10)	172.7
O4—H4···O1W	0.84	1.76	2.572 (4)	162.1
O1W—H2W···O8	0.855 (11)	2.13 (3)	2.827 (5)	138 (4)
O1W—H1W···O1ⁱⁱⁱ	0.860 (11)	1.892 (16)	2.734 (3)	166 (4)

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

Acknowledgements

This work was supported financially by the Foundation for University Key Teachers of the Education Department of Hunan Province and the Key Subject Construction Project of Hunan Province (No. 2006–180).

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