catena-Poly[[[bis­(4-amino­benzoato-κO)copper(II)]-μ-1,1′-(pentane-1,5-di­yl)diimidazole] trihydrate]

Zhang, W.-L.; Zhang, L.-P.; Ma, J.-F.

doi:10.1107/S1600536807064586

metal-organic compounds

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ISSN: 2056-9890

Volume 64| Part 1| January 2008| Pages m156-m157

https://doi.org/10.1107/S1600536807064586

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catena-Poly[[[bis(4-aminobenzoato-κO)copper(II)]-μ-1,1′-(pentane-1,5-diyl)diimidazole] trihydrate]

Wen-Li Zhang,^a Lai-Ping Zhang ^a and Jian-Fang Ma ^a ^*

^aDepartment of Chemistry, Northeast Normal University, Changchun 130024, People's Republic of China
^*Correspondence e-mail: majf247nenu@yahoo.com.cn

(Received 19 November 2007; accepted 29 November 2007; online 12 December 2007)

In the title compound, {[Cu(C₇H₆NO₂)₂(C₁₁H₁₆N₄)]·3H₂O}_n, each Cu^II atom is coordinated by two O atoms from two 4-aminobenzoate anions, and two N atoms from two different 1,1′-(pentane-1,5-diyl)diimidazole (biim-5) ligands, to furnish a distorted square-planar geometry. The biim-5 ligand coordinates to two copper(II) cations, acting as a bridging ligand; as a result the copper(II) cations are connected to form an infinite chain structure. The polymeric chains are linked through a variety of hydrogen bonds to form a three-dimensional structure.

Related literature

For related literature, see: Batten & Robson (1998 ); Chen & Gao (2002 ); Ma et al. (2000 ); Moulton & Zaworotko (2001 ); Tong et al. (2002 ); Yang et al. (2005 , 2006 ).

Experimental

Crystal data

[Cu(C₇H₆NO₂)₂(C₁₁H₁₆N₄)]·3H₂O
M_r = 594.12
Monoclinic, P 2₁ /n
a = 13.082 (9) Å
b = 11.151 (1) Å
c = 19.505 (2) Å
β = 93.725 (1)°
V = 2839.3 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.82 mm⁻¹
T = 293 (2) K
0.68 × 0.45 × 0.38 mm

Data collection

Bruker APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.635, T_max = 0.746
16576 measured reflections
6488 independent reflections
4988 reflections with I > 2σ(I)
R_int = 0.028

Refinement

R[F² > 2σ(F²)] = 0.033
wR(F²) = 0.095
S = 1.03
6488 reflections
382 parameters
12 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.41 e Å⁻³
Δρ_min = −0.34 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2W—H2A⋯O4ⁱ	0.86 (3)	2.09 (3)	2.954 (3)	174 (4)
N5—H5A⋯O1Wⁱⁱ	0.79 (3)	2.32 (3)	3.100 (3)	172 (5)
N6—H6B⋯O1Wⁱⁱⁱ	0.88 (4)	2.18 (4)	3.046 (3)	170 (5)
O1W—H1A⋯O2W	0.86 (3)	1.95 (3)	2.805 (3)	172 (5)
O1W—H1B⋯O4	0.87 (3)	1.96 (3)	2.802 (2)	163 (4)
O2W—H2B⋯O1	0.94 (3)	2.01 (3)	2.889 (3)	155 (4)
O3W—H3A⋯O2	0.89 (3)	1.87 (3)	2.734 (3)	164 (4)
Symmetry codes: (i) -x+1, -y, -z+1; (ii) $[-x+{\script{3\over 2}}, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (iii) $[-x+{\script{3\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 1997 ); cell refinement: SAINT (Bruker, 1999 ); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL-Plus (Sheldrick, 1990 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536807064586/sf2009sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536807064586/sf2009Isup2.hkl

checkCIF report

Comment top

In recent years, research into coordination polymers has been expanding rapidly because of their fascinating structural diversity and potential application as functional materials (Batten & Robson, 1998; Moulton & Zaworotko, 2001). To date, a number of one-, two- and three-dimensional infinite frameworks have been generated with linear N,N'-bidentate spacers (Tong et al., 2002). Much of the work has been focused on coordination polymers with rigid ligands, such as 4,4'-bipyridine, pyrazine and their analogues. In our previous work, we have synthsis some compounds contaning 1,1'-(1,4-butanediyl)bis(imidazole) (Ma et al., 2000; Yang et al., 2006). However, flexible ligands such as 1,1'-(1,5-pentanediyl) bis(imidazole) have not been well explored to date. In the present paper, we report the preparation and crystal structure of three-dimensional supermolecule coordination polymer of compound, (I).

As shown in Fig. 1, each Cu^II atom is primarily coordinated by two oxygen atoms from two para-aminobenzoate anions, and two nitrogen atoms from two different biim-5 ligands, to furnish a distorted square-planar geometry. The Cu—N distances range from 1.967 (2) to 1.975 (2) Å, which are similar to reported Cu—N distances. The Cu1—O distances of 1.970 (1) and 1.976 (1) Å are also similar to reported Cu—O distances (Yang et al., 2006). The pendant carboxy oxygen atoms have weak bonding interactions with the Cu^II atom at the axial sites due to the Jahn-Teller effect. The Cu—O distances range from 2.712 to 2.727 Å, which indicated the weak bonding interactions. Each biim-5 ligand coordinates to two Cu^II atoms, acting as a bridging ligand and as a result, an one-dimensional chain structure is formed.

The hydrogen bonds in this study have been considered with liberal distance cut-off criteria of 2.5< D···A < 3.0 Å and 120 < D—H···A < 180 °. The selected hydrogen-bond distances and angles are listed in Table 2. It can be seen that there are three H atoms involved in hydrogen bonding in the asymmetric unit, two of which are from amino group and one of which from water molecules. The uncoordinated carboxylate O atoms are also involved in hydrogen bonds and play the role of acceptors. The polymeric chains are connected through various hydrogen bonds to form a three-dimensional structure (Fig. 2).

Related literature top

For related literature, see: Batten & Robson (1998); Chen & Gao (2002); Ma et al. (2000); Moulton & Zaworotko (2001); Tong et al. (2002); Yang et al., (2005, 2006).

Experimental top

A mixture of CuCl₂.2H₂O (0.171 g, 1 mmol), NaOH (0.08 g, 2 mmol) in water was stirring for 10 min at room temperature, then the Cu(OH)₂ solid was filtered. P-aminobenzoic acid was added to the Cu(OH)₂ suspension in water with stirring. Then biim-5 (0.204 g, 1 mmol) in ethanol was added with stirring for 1 h and blue precipitate was obtained. And then a minimum amount of ammonia (14 M) was added to get the blue solution. Suitable blue crystals were obtained from the filtrate after standing at room temperature for several days.

Structure description top

For related literature, see: Batten & Robson (1998); Chen & Gao (2002); Ma et al. (2000); Moulton & Zaworotko (2001); Tong et al. (2002); Yang et al., (2005, 2006).

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SMART (Bruker, 1997); data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL-Plus (Sheldrick, 1990); software used to prepare material for publication: SHELXL97.

Figures top

	Fig. 1. View of the compound (I). Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. View of the three-dimensional superamolecular structure of (I). The hydrogen bonds are shown as dotted lines. H atoms on the C atoms have been omiited for clarity.

catena-poly[[[bis(4-aminobenzoato-κO)copper(II)]-µ- 1,1'-(pentane-1,5-diyl)diimidazole] trihydrate] top

Crystal data top

[Cu(C₇H₆NO₂)₂(C₁₁H₁₆N₄)]·3H₂O	F(000) = 1244
M_r = 594.12	D_x = 1.390 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71069 Å
Hall symbol: -P 2yn	Cell parameters from 6488 reflections
a = 13.082 (9) Å	θ = 1.8–28.5°
b = 11.151 (1) Å	µ = 0.82 mm⁻¹
c = 19.505 (2) Å	T = 293 K
β = 93.725 (1)°	Block, blue
V = 2839.3 (4) Å³	0.68 × 0.45 × 0.38 mm
Z = 4

Data collection top

Bruker APEX CCD area-detector diffractometer	6488 independent reflections
Radiation source: fine-focus sealed tube	4988 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.028
ω scans	θ_max = 28.5°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −17→9
T_min = 0.635, T_max = 0.746	k = −14→13
16576 measured reflections	l = −25→26

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)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.095	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ²(F_o²) + (0.0448P)² + 0.6476P] where P = (F_o² + 2F_c²)/3
6488 reflections	(Δ/σ)_max = 0.002
382 parameters	Δρ_max = 0.41 e Å⁻³
12 restraints	Δρ_min = −0.34 e Å⁻³

Crystal data top

[Cu(C₇H₆NO₂)₂(C₁₁H₁₆N₄)]·3H₂O	V = 2839.3 (4) Å³
M_r = 594.12	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 13.082 (9) Å	µ = 0.82 mm⁻¹
b = 11.151 (1) Å	T = 293 K
c = 19.505 (2) Å	0.68 × 0.45 × 0.38 mm
β = 93.725 (1)°

Data collection top

Bruker APEX CCD area-detector diffractometer	6488 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	4988 reflections with I > 2σ(I)
T_min = 0.635, T_max = 0.746	R_int = 0.028
16576 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.033	12 restraints
wR(F²) = 0.095	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.41 e Å⁻³
6488 reflections	Δρ_min = −0.34 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
Cu1	0.724906 (17)	0.20985 (2)	0.494309 (9)	0.03977 (9)
C1	0.69874 (15)	0.25416 (18)	0.70179 (8)	0.0414 (4)
C2	0.63431 (17)	0.1687 (2)	0.72737 (9)	0.0515 (5)
H2	0.5989	0.1165	0.6971	0.062*
C3	0.62168 (18)	0.1595 (2)	0.79711 (10)	0.0578 (5)
H3	0.5772	0.1024	0.8131	0.069*
C4	0.67506 (17)	0.2352 (2)	0.84349 (9)	0.0503 (5)
C5	0.74098 (18)	0.32010 (19)	0.81822 (10)	0.0521 (5)
H5	0.7778	0.3708	0.8485	0.063*
C6	0.75202 (17)	0.32954 (18)	0.74842 (10)	0.0480 (4)
H6	0.7958	0.3873	0.7323	0.058*
C7	0.71394 (15)	0.26575 (18)	0.62690 (9)	0.0437 (4)
C8	0.72368 (15)	0.13276 (17)	0.28845 (8)	0.0437 (4)
C9	0.66706 (18)	0.05414 (19)	0.24653 (10)	0.0543 (5)
H9	0.6230	0.0002	0.2659	0.065*
C10	0.6749 (2)	0.0543 (2)	0.17607 (10)	0.0605 (6)
H10	0.6364	0.0002	0.1488	0.073*
C11	0.73957 (18)	0.1343 (2)	0.14575 (9)	0.0531 (5)
C12	0.79721 (18)	0.21209 (19)	0.18774 (10)	0.0531 (5)
H12	0.8418	0.2653	0.1684	0.064*
C13	0.78948 (16)	0.21189 (18)	0.25818 (9)	0.0483 (5)
H13	0.8287	0.2652	0.2855	0.058*
C14	0.71565 (16)	0.1321 (2)	0.36461 (9)	0.0487 (5)
C15	0.88170 (14)	0.07802 (17)	0.58180 (9)	0.0418 (4)
H15	0.8333	0.0438	0.6087	0.050*
C16	0.95172 (16)	0.17479 (19)	0.50186 (10)	0.0484 (5)
H16	0.9602	0.2202	0.4626	0.058*
C17	1.02826 (16)	0.1299 (2)	0.54402 (10)	0.0536 (5)
H17	1.0982	0.1392	0.5396	0.064*
C18	1.03590 (17)	0.0044 (2)	0.65268 (10)	0.0568 (6)
H18A	1.0945	−0.0381	0.6367	0.068*
H18B	0.9898	−0.0544	0.6704	0.068*
C19	1.07186 (15)	0.0899 (2)	0.71027 (10)	0.0565 (5)
H19A	1.1139	0.0454	0.7443	0.068*
H19B	1.1148	0.1509	0.6914	0.068*
C20	0.98658 (16)	0.15138 (19)	0.74596 (10)	0.0529 (5)
H20A	1.0170	0.2083	0.7789	0.063*
H20B	0.9449	0.1964	0.7120	0.063*
C21	0.91748 (15)	0.0677 (2)	0.78300 (10)	0.0549 (5)
H21A	0.8871	0.0110	0.7499	0.066*
H21B	0.8622	0.1146	0.8003	0.066*
C22	0.96906 (17)	−0.00216 (19)	0.84230 (10)	0.0541 (5)
H22A	0.9211	−0.0603	0.8585	0.065*
H22B	1.0269	−0.0458	0.8261	0.065*
C23	1.09798 (15)	0.12327 (18)	0.90985 (9)	0.0438 (4)
H23	1.1518	0.1089	0.8820	0.053*
C24	1.00978 (16)	0.18889 (19)	0.99050 (10)	0.0501 (5)
H24	0.9912	0.2289	1.0296	0.060*
C25	0.94779 (16)	0.1173 (2)	0.95058 (10)	0.0546 (5)
H25	0.8794	0.0999	0.9566	0.065*
N1	0.85934 (12)	0.14264 (14)	0.52616 (7)	0.0413 (3)
N2	0.98308 (12)	0.06823 (15)	0.59449 (7)	0.0443 (4)
N3	1.00482 (12)	0.07559 (14)	0.89960 (7)	0.0429 (4)
N4	1.10431 (12)	0.19343 (14)	0.96448 (7)	0.0422 (4)
N5	0.6617 (2)	0.2274 (2)	0.91329 (9)	0.0714 (6)
N6	0.7484 (2)	0.1342 (2)	0.07524 (9)	0.0745 (7)
O1	0.67388 (10)	0.18549 (13)	0.58642 (6)	0.0461 (3)
O2	0.76375 (14)	0.35143 (14)	0.60610 (7)	0.0639 (4)
O1W	0.69005 (16)	−0.12845 (16)	0.48742 (9)	0.0730 (5)
O3	0.76716 (11)	0.21141 (14)	0.39921 (6)	0.0529 (4)
O2W	0.55952 (17)	−0.03625 (18)	0.58310 (12)	0.0875 (6)
O4	0.65989 (14)	0.05708 (15)	0.39138 (7)	0.0671 (4)
O3W	0.8944 (2)	0.4784 (2)	0.52971 (15)	0.1152 (9)
H5A	0.704 (3)	0.261 (4)	0.937 (2)	0.173*
H5B	0.638 (4)	0.161 (3)	0.927 (2)	0.173*
H6A	0.698 (3)	0.091 (4)	0.051 (2)	0.173*
H6B	0.774 (4)	0.199 (4)	0.058 (2)	0.173*
H1A	0.645 (3)	−0.104 (4)	0.5145 (18)	0.173*
H1B	0.691 (3)	−0.078 (4)	0.4530 (17)	0.173*
H2A	0.496 (2)	−0.038 (4)	0.593 (2)	0.173*
H2B	0.577 (3)	0.045 (3)	0.584 (2)	0.173*
H3A	0.845 (2)	0.436 (4)	0.547 (2)	0.173*
H3B	0.952 (2)	0.449 (4)	0.558 (2)	0.173*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.04202 (14)	0.05555 (15)	0.02164 (11)	0.00707 (10)	0.00120 (8)	0.00176 (9)
C1	0.0499 (11)	0.0473 (10)	0.0272 (8)	0.0124 (9)	0.0031 (8)	0.0012 (7)
C2	0.0583 (12)	0.0659 (13)	0.0305 (9)	−0.0015 (10)	0.0036 (9)	−0.0037 (9)
C3	0.0654 (14)	0.0754 (14)	0.0333 (9)	−0.0059 (12)	0.0091 (9)	0.0021 (10)
C4	0.0611 (13)	0.0621 (13)	0.0282 (8)	0.0174 (10)	0.0062 (9)	−0.0008 (8)
C5	0.0675 (13)	0.0528 (12)	0.0353 (9)	0.0119 (10)	−0.0025 (9)	−0.0088 (8)
C6	0.0589 (12)	0.0454 (10)	0.0397 (9)	0.0064 (9)	0.0047 (9)	−0.0004 (8)
C7	0.0484 (11)	0.0519 (11)	0.0313 (9)	0.0139 (9)	0.0055 (8)	0.0052 (8)
C8	0.0519 (11)	0.0521 (11)	0.0274 (8)	0.0174 (9)	0.0044 (8)	0.0053 (8)
C9	0.0648 (13)	0.0584 (12)	0.0400 (10)	0.0036 (11)	0.0061 (10)	0.0058 (9)
C10	0.0808 (16)	0.0640 (14)	0.0361 (10)	0.0039 (12)	−0.0013 (10)	−0.0023 (10)
C11	0.0728 (14)	0.0586 (12)	0.0281 (8)	0.0209 (11)	0.0048 (9)	0.0041 (8)
C12	0.0677 (14)	0.0582 (12)	0.0346 (9)	0.0090 (10)	0.0111 (9)	0.0085 (9)
C13	0.0572 (12)	0.0550 (12)	0.0327 (9)	0.0100 (10)	0.0038 (8)	0.0013 (8)
C14	0.0523 (11)	0.0641 (13)	0.0302 (9)	0.0259 (10)	0.0063 (8)	0.0084 (9)
C15	0.0431 (10)	0.0515 (10)	0.0308 (8)	0.0052 (8)	0.0017 (7)	0.0023 (8)
C16	0.0497 (11)	0.0607 (12)	0.0354 (9)	0.0012 (10)	0.0068 (8)	0.0043 (9)
C17	0.0410 (10)	0.0758 (14)	0.0446 (10)	0.0005 (10)	0.0069 (9)	−0.0010 (10)
C18	0.0539 (12)	0.0754 (14)	0.0403 (10)	0.0257 (11)	−0.0038 (9)	0.0039 (10)
C19	0.0414 (10)	0.0871 (16)	0.0398 (10)	−0.0031 (11)	−0.0065 (8)	0.0059 (10)
C20	0.0565 (12)	0.0582 (12)	0.0419 (10)	0.0009 (10)	−0.0120 (9)	−0.0039 (9)
C21	0.0413 (10)	0.0783 (14)	0.0442 (10)	−0.0032 (10)	−0.0038 (9)	−0.0154 (10)
C22	0.0603 (13)	0.0522 (12)	0.0496 (11)	−0.0180 (10)	0.0012 (10)	−0.0102 (9)
C23	0.0428 (10)	0.0544 (11)	0.0343 (9)	−0.0051 (9)	0.0036 (8)	−0.0047 (8)
C24	0.0476 (11)	0.0656 (13)	0.0379 (10)	−0.0019 (10)	0.0077 (8)	−0.0067 (9)
C25	0.0414 (10)	0.0752 (14)	0.0479 (11)	−0.0067 (10)	0.0086 (9)	−0.0042 (10)
N1	0.0418 (8)	0.0544 (9)	0.0276 (7)	0.0055 (7)	0.0024 (6)	0.0011 (6)
N2	0.0422 (8)	0.0580 (10)	0.0321 (7)	0.0108 (7)	−0.0011 (6)	0.0000 (7)
N3	0.0445 (8)	0.0481 (9)	0.0358 (7)	−0.0073 (7)	0.0003 (7)	−0.0021 (7)
N4	0.0422 (8)	0.0558 (9)	0.0285 (7)	−0.0049 (7)	0.0018 (6)	−0.0013 (6)
N5	0.0936 (17)	0.0929 (17)	0.0282 (8)	0.0059 (13)	0.0091 (9)	−0.0018 (9)
N6	0.1137 (19)	0.0827 (15)	0.0279 (8)	0.0114 (13)	0.0109 (10)	0.0024 (9)
O1	0.0482 (7)	0.0655 (9)	0.0245 (6)	0.0049 (6)	0.0022 (5)	0.0000 (6)
O2	0.0887 (12)	0.0600 (9)	0.0449 (8)	−0.0038 (9)	0.0186 (8)	0.0064 (7)
O1W	0.0865 (12)	0.0683 (11)	0.0655 (11)	0.0060 (9)	0.0135 (9)	0.0146 (9)
O3	0.0486 (8)	0.0851 (11)	0.0250 (6)	0.0149 (7)	0.0024 (6)	0.0009 (6)
O2W	0.0846 (13)	0.0803 (13)	0.0985 (15)	−0.0034 (11)	0.0133 (12)	−0.0157 (11)
O4	0.0865 (12)	0.0744 (10)	0.0425 (8)	0.0088 (9)	0.0203 (8)	0.0176 (7)
O3W	0.130 (2)	0.0837 (15)	0.140 (2)	0.0016 (14)	0.0703 (18)	0.0213 (14)

Geometric parameters (Å, º) top

Cu1—N4ⁱ	1.9677 (15)	C17—N2	1.367 (3)
Cu1—O3	1.9698 (12)	C17—H17	0.9300
Cu1—N1	1.9745 (15)	C18—N2	1.473 (2)
Cu1—O1	1.9757 (12)	C18—C19	1.524 (3)
C1—C2	1.387 (3)	C18—H18A	0.9700
C1—C6	1.392 (3)	C18—H18B	0.9700
C1—C7	1.493 (2)	C19—C20	1.517 (3)
C2—C3	1.385 (2)	C19—H19A	0.9700
C2—H2	0.9300	C19—H19B	0.9700
C3—C4	1.391 (3)	C20—C21	1.515 (3)
C3—H3	0.9300	C20—H20A	0.9700
C4—N5	1.387 (2)	C20—H20B	0.9700
C4—C5	1.392 (3)	C21—C22	1.516 (3)
C5—C6	1.382 (3)	C21—H21A	0.9700
C5—H5	0.9300	C21—H21B	0.9700
C6—H6	0.9300	C22—N3	1.467 (2)
C7—O2	1.239 (2)	C22—H22A	0.9700
C7—O1	1.283 (2)	C22—H22B	0.9700
C8—C9	1.381 (3)	C23—N4	1.320 (2)
C8—C13	1.391 (3)	C23—N3	1.333 (2)
C8—C14	1.496 (2)	C23—H23	0.9300
C9—C10	1.385 (3)	C24—C25	1.349 (3)
C9—H9	0.9300	C24—N4	1.368 (2)
C10—C11	1.389 (3)	C24—H24	0.9300
C10—H10	0.9300	C25—N3	1.363 (2)
C11—C12	1.383 (3)	C25—H25	0.9300
C11—N6	1.387 (2)	N4—Cu1ⁱⁱ	1.9677 (15)
C12—C13	1.384 (3)	N5—H5A	0.79 (3)
C12—H12	0.9300	N5—H5B	0.86 (3)
C13—H13	0.9300	N6—H6A	0.92 (3)
C14—O4	1.247 (3)	N6—H6B	0.88 (4)
C14—O3	1.278 (3)	O1W—H1A	0.86 (3)
C15—N1	1.320 (2)	O1W—H1B	0.87 (3)
C15—N2	1.338 (2)	O2W—H2A	0.86 (3)
C15—H15	0.9300	O2W—H2B	0.94 (3)
C16—C17	1.350 (3)	O3W—H3A	0.89 (3)
C16—N1	1.374 (2)	O3W—H3B	0.97 (3)
C16—H16	0.9300

N4ⁱ—Cu1—O3	89.16 (6)	N2—C18—H18B	109.2
N4ⁱ—Cu1—N1	169.04 (7)	C19—C18—H18B	109.2
O3—Cu1—N1	90.06 (6)	H18A—C18—H18B	107.9
N4ⁱ—Cu1—O1	91.86 (6)	C20—C19—C18	114.84 (17)
O3—Cu1—O1	171.77 (6)	C20—C19—H19A	108.6
N1—Cu1—O1	90.48 (6)	C18—C19—H19A	108.6
C2—C1—C6	118.06 (16)	C20—C19—H19B	108.6
C2—C1—C7	122.31 (17)	C18—C19—H19B	108.6
C6—C1—C7	119.62 (18)	H19A—C19—H19B	107.5
C3—C2—C1	121.22 (19)	C21—C20—C19	114.83 (18)
C3—C2—H2	119.4	C21—C20—H20A	108.6
C1—C2—H2	119.4	C19—C20—H20A	108.6
C2—C3—C4	120.5 (2)	C21—C20—H20B	108.6
C2—C3—H3	119.8	C19—C20—H20B	108.6
C4—C3—H3	119.8	H20A—C20—H20B	107.5
N5—C4—C3	120.7 (2)	C20—C21—C22	115.50 (17)
N5—C4—C5	120.7 (2)	C20—C21—H21A	108.4
C3—C4—C5	118.60 (17)	C22—C21—H21A	108.4
C6—C5—C4	120.47 (19)	C20—C21—H21B	108.4
C6—C5—H5	119.8	C22—C21—H21B	108.4
C4—C5—H5	119.8	H21A—C21—H21B	107.5
C5—C6—C1	121.2 (2)	N3—C22—C21	112.43 (17)
C5—C6—H6	119.4	N3—C22—H22A	109.1
C1—C6—H6	119.4	C21—C22—H22A	109.1
O2—C7—O1	122.61 (16)	N3—C22—H22B	109.1
O2—C7—C1	119.56 (18)	C21—C22—H22B	109.1
O1—C7—C1	117.83 (17)	H22A—C22—H22B	107.8
C9—C8—C13	118.32 (17)	N4—C23—N3	111.48 (16)
C9—C8—C14	121.02 (19)	N4—C23—H23	124.3
C13—C8—C14	120.66 (19)	N3—C23—H23	124.3
C8—C9—C10	121.0 (2)	C25—C24—N4	109.38 (17)
C8—C9—H9	119.5	C25—C24—H24	125.3
C10—C9—H9	119.5	N4—C24—H24	125.3
C9—C10—C11	120.6 (2)	C24—C25—N3	106.62 (17)
C9—C10—H10	119.7	C24—C25—H25	126.7
C11—C10—H10	119.7	N3—C25—H25	126.7
C12—C11—N6	120.7 (2)	C15—N1—C16	105.85 (16)
C12—C11—C10	118.36 (17)	C15—N1—Cu1	127.69 (13)
N6—C11—C10	120.9 (2)	C16—N1—Cu1	125.30 (13)
C11—C12—C13	121.0 (2)	C15—N2—C17	107.20 (15)
C11—C12—H12	119.5	C15—N2—C18	126.28 (17)
C13—C12—H12	119.5	C17—N2—C18	126.52 (17)
C12—C13—C8	120.6 (2)	C23—N3—C25	107.03 (16)
C12—C13—H13	119.7	C23—N3—C22	126.39 (16)
C8—C13—H13	119.7	C25—N3—C22	126.51 (17)
O4—C14—O3	123.10 (17)	C23—N4—C24	105.47 (16)
O4—C14—C8	120.0 (2)	C23—N4—Cu1ⁱⁱ	124.79 (13)
O3—C14—C8	116.91 (18)	C24—N4—Cu1ⁱⁱ	129.60 (13)
N1—C15—N2	111.15 (16)	C4—N5—H5A	114 (4)
N1—C15—H15	124.4	C4—N5—H5B	116 (3)
N2—C15—H15	124.4	H5A—N5—H5B	119 (4)
C17—C16—N1	109.12 (17)	C11—N6—H6A	114 (3)
C17—C16—H16	125.4	C11—N6—H6B	116 (3)
N1—C16—H16	125.4	H6A—N6—H6B	122 (4)
C16—C17—N2	106.67 (17)	C7—O1—Cu1	108.37 (12)
C16—C17—H17	126.7	H1A—O1W—H1B	108 (3)
N2—C17—H17	126.7	C14—O3—Cu1	108.70 (12)
N2—C18—C19	111.85 (18)	H2A—O2W—H2B	105 (3)
N2—C18—H18A	109.2	H3A—O3W—H3B	99 (3)
C19—C18—H18A	109.2

C6—C1—C2—C3	1.1 (3)	N2—C15—N1—C16	0.5 (2)
C7—C1—C2—C3	179.84 (19)	N2—C15—N1—Cu1	−167.55 (13)
C1—C2—C3—C4	−1.1 (3)	C17—C16—N1—C15	−0.8 (2)
C2—C3—C4—N5	179.2 (2)	C17—C16—N1—Cu1	167.69 (14)
C2—C3—C4—C5	0.2 (3)	N4ⁱ—Cu1—N1—C15	119.0 (3)
N5—C4—C5—C6	−178.3 (2)	O3—Cu1—N1—C15	−155.13 (17)
C3—C4—C5—C6	0.7 (3)	O1—Cu1—N1—C15	16.65 (17)
C4—C5—C6—C1	−0.6 (3)	N4ⁱ—Cu1—N1—C16	−46.9 (4)
C2—C1—C6—C5	−0.2 (3)	O3—Cu1—N1—C16	38.96 (16)
C7—C1—C6—C5	−179.02 (18)	O1—Cu1—N1—C16	−149.25 (16)
C2—C1—C7—O2	172.4 (2)	N1—C15—N2—C17	−0.1 (2)
C6—C1—C7—O2	−8.8 (3)	N1—C15—N2—C18	179.02 (18)
C2—C1—C7—O1	−7.3 (3)	C16—C17—N2—C15	−0.4 (2)
C6—C1—C7—O1	171.39 (18)	C16—C17—N2—C18	−179.49 (19)
C13—C8—C9—C10	−0.4 (3)	C19—C18—N2—C15	−99.2 (2)
C14—C8—C9—C10	−179.67 (19)	C19—C18—N2—C17	79.8 (2)
C8—C9—C10—C11	−0.4 (3)	N4—C23—N3—C25	0.0 (2)
C9—C10—C11—C12	1.2 (3)	N4—C23—N3—C22	177.13 (18)
C9—C10—C11—N6	179.4 (2)	C24—C25—N3—C23	−0.5 (2)
N6—C11—C12—C13	−179.4 (2)	C24—C25—N3—C22	−177.63 (19)
C10—C11—C12—C13	−1.1 (3)	C21—C22—N3—C23	−93.1 (2)
C11—C12—C13—C8	0.3 (3)	C21—C22—N3—C25	83.5 (2)
C9—C8—C13—C12	0.5 (3)	N3—C23—N4—C24	0.5 (2)
C14—C8—C13—C12	179.72 (17)	N3—C23—N4—Cu1ⁱⁱ	−175.54 (12)
C9—C8—C14—O4	2.5 (3)	C25—C24—N4—C23	−0.8 (2)
C13—C8—C14—O4	−176.73 (18)	C25—C24—N4—Cu1ⁱⁱ	174.99 (15)
C9—C8—C14—O3	−176.92 (18)	O2—C7—O1—Cu1	9.2 (2)
C13—C8—C14—O3	3.8 (3)	C1—C7—O1—Cu1	−171.10 (13)
N1—C16—C17—N2	0.7 (2)	N4ⁱ—Cu1—O1—C7	−94.66 (13)
N2—C18—C19—C20	65.9 (2)	N1—Cu1—O1—C7	74.64 (13)
C18—C19—C20—C21	62.9 (2)	O4—C14—O3—Cu1	−9.3 (2)
C19—C20—C21—C22	63.4 (2)	C8—C14—O3—Cu1	170.13 (12)
C20—C21—C22—N3	66.3 (2)	N4ⁱ—Cu1—O3—C14	−80.43 (13)
N4—C24—C25—N3	0.8 (2)	N1—Cu1—O3—C14	110.50 (13)

Symmetry codes: (i) x−1/2, −y+1/2, z−1/2; (ii) 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
O2W—H2A···O4ⁱⁱⁱ	0.86 (3)	2.09 (3)	2.954 (3)	174 (4)
N5—H5A···O1W^iv	0.79 (3)	2.32 (3)	3.100 (3)	172 (5)
N6—H6B···O1W^v	0.88 (4)	2.18 (4)	3.046 (3)	170 (5)
O1W—H1A···O2W	0.86 (3)	1.95 (3)	2.805 (3)	172 (5)
O1W—H1B···O4	0.87 (3)	1.96 (3)	2.802 (2)	163 (4)
O2W—H2B···O1	0.94 (3)	2.01 (3)	2.889 (3)	155 (4)
O3W—H3A···O2	0.89 (3)	1.87 (3)	2.734 (3)	164 (4)

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

Experimental details

Crystal data
Chemical formula	[Cu(C₇H₆NO₂)₂(C₁₁H₁₆N₄)]·3H₂O
M_r	594.12
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	293
a, b, c (Å)	13.082 (9), 11.151 (1), 19.505 (2)
β (°)	93.725 (1)
V (Å³)	2839.3 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.82
Crystal size (mm)	0.68 × 0.45 × 0.38

Data collection
Diffractometer	Bruker APEX CCD area-detector
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.635, 0.746
No. of measured, independent and observed [I > 2σ(I)] reflections	16576, 6488, 4988
R_int	0.028
(sin θ/λ)_max (Å⁻¹)	0.671

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.033, 0.095, 1.03
No. of reflections	6488
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)	0.41, −0.34

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1999), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL-Plus (Sheldrick, 1990), SHELXL97.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2W—H2A···O4ⁱ	0.86 (3)	2.09 (3)	2.954 (3)	174 (4)
N5—H5A···O1Wⁱⁱ	0.79 (3)	2.32 (3)	3.100 (3)	172 (5)
N6—H6B···O1Wⁱⁱⁱ	0.88 (4)	2.18 (4)	3.046 (3)	170 (5)
O1W—H1A···O2W	0.86 (3)	1.95 (3)	2.805 (3)	172 (5)
O1W—H1B···O4	0.87 (3)	1.96 (3)	2.802 (2)	163 (4)
O2W—H2B···O1	0.94 (3)	2.01 (3)	2.889 (3)	155 (4)
O3W—H3A···O2	0.89 (3)	1.87 (3)	2.734 (3)	164 (4)

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

Acknowledgements

The authors thank the National Natural Science Foundation of China (grant No. 20471014), the Program for New Century Excellent Talents in Chinese Universities (grant No. NCET-05-0320), the Fok Ying Tung Education Foundation, and the Analysis and Testing Foundation of Northeast Normal University for support.

References

Batten, S. R. & Robson, R. (1998). Angew. Chem. Int. Ed. 37, 1460–1491. CrossRef Google Scholar
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Bruker (1999). SAINT. Version 6.02. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
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Sheldrick, G. M. (1990). SHELXTL-Plus. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA. Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
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Volume 64| Part 1| January 2008| Pages m156-m157

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

catena-Poly[[[bis­­(4-amino­benzoato-κO)copper(II)]-μ-1,1′-(pentane-1,5-di­yl)di­imidazole] trihydrate]

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

metal-organic compounds

catena-Poly[[[bis(4-aminobenzoato-κO)copper(II)]-μ-1,1′-(pentane-1,5-diyl)diimidazole] trihydrate]