Poly[[aqua­bis­[μ2-6-(pyridine-3-car­box­amido)­naphthalene-2-carboxyl­ato]copper(II)] dihydrate]

Song, Y.-S.; Lee, S.W.

doi:10.1107/S1600536812044157

metal-organic compounds

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ISSN: 2056-9890

Volume 68| Part 11| November 2012| Page m1422

doi:10.1107/S1600536812044157

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Poly[[aquabis[μ₂-6-(pyridine-3-carboxamido)naphthalene-2-carboxylato]copper(II)] dihydrate]

Yun-Sung Song ^a and Soon W. Lee ^a ^*

^aDepartment of Chemistry (BK21), Sungkyunkwan University, Natural Science Campus, Suwon 440-746, Republic of Korea
^*Correspondence e-mail: soonwlee@skku.edu

(Received 12 July 2012; accepted 24 October 2012; online 31 October 2012)

The title compound, {[Cu(C₁₇H₁₁N₂O₃)₂(H₂O)]·2H₂O}_n, is a two-dimensional polymer. The Cu²⁺ ion lies on the crystallographic twofold axis. The coordination sphere of the Cu²⁺ ion can be described as a distorted square pyramid. All of the H atoms in the amide group and lattice water molecules participate in O—H⋯O or N—H⋯O hydrogen bonding to strengthen the two-dimensioal framework of the polymer.

Related literature

For coordination polymers based on linking ligands with O- and N-donor atoms, see: Robin & Fromm (2006 ). For d–f coordination polymers based on linking ligands with pyridyl–carboxylate terminal ligands, see: Hu et al. (2012 ); Chen et al. (2010 ); Tang et al. (2010 ); Yue et al. (2011 ); Zhu et al. (2010 ). For related potential linking ligands, see: Han & Lee (2012 ); Zheng & Lee (2012 ). For the ligand used for the preparation of the title compound, see: Song & Lee (2012 ).

Experimental

Crystal data

[Cu(C₁₇H₁₁N₂O₃)₂(H₂O)]·2H₂O
M_r = 700.14
Monoclinic, C 2/c
a = 29.6255 (8) Å
b = 6.8582 (2) Å
c = 14.8264 (4) Å
β = 94.728 (3)°
V = 3002.14 (14) Å³
Z = 4
Mo Kα radiation
μ = 0.79 mm⁻¹
T = 296 K
0.18 × 0.16 × 0.16 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.870, T_max = 0.884
24367 measured reflections
3705 independent reflections
2462 reflections with I > 2σ(I)
R_int = 0.071

Refinement

R[F² > 2σ(F²)] = 0.045
wR(F²) = 0.095
S = 1.00
3705 reflections
234 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.31 e Å⁻³
Δρ_min = −0.28 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O5ⁱ	0.81 (3)	2.07 (3)	2.857 (4)	164 (3)
O5—H51⋯O2ⁱⁱ	0.75 (4)	2.13 (4)	2.861 (3)	164 (4)
O5—H52⋯O3	0.77 (4)	2.04 (4)	2.811 (4)	177 (5)
O4—H4⋯O2ⁱⁱⁱ	0.90 (3)	1.95 (3)	2.820 (3)	163 (3)
Symmetry codes: (i) x, y-1, z; (ii) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (iii) x, y+1, z.

Data collection: APEX2 (Bruker, 2008 ); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Bruker, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812044157/aa2070sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812044157/aa2070Isup2.hkl

checkCIF report

Comment top

Coordination polymers are prepared by employing a wide variety of linking ligands possessing pyridyl–pyridyl, pyridyl–amine, furan–furan, thiophene–thiophene, or pyridyl–carboxylate terminals. For instance, bis(pyridyl)- and dicarboxylate-type linking ligands have long been utilized in preparing such polymers (Robin & Fromm, 2006). In particular, those containing the pyridyl–carboxylate terminals are intriguing due to the presence of both a harder carboxylate oxygen donor and a softer pyridyl nitrogen donor in them. The ligands of this type were employed to prepare unique polymers containing both d- and f-block metals within their frameworks (Hu et al., 2012; Chen et al., 2010; Tang et al., 2010; Yue et al., 2011; Zhu et al., 2010). 6-(Nicotinamido)-2-naphthoic acid (HL) belongs to the pyridyl–carboxylate-type linking ligands, and we recently reported its preparation and structure (Song & Lee, 2012). Our research group also reported the molecular structures of two other related linking ligands (Han & Lee, 2012; Zheng & Lee, 2012). We report herein the structure of a two-dimensional Cu polymer of the HL ligand, which is the first d-block coordination polymer of this ligand.

Fig. 1 shows an asymmetric unit of the title polymer, which consists of one half Cu²⁺ ion, one 6-(nicotinamido)-2-naphthoato ligand (L), one half aqua ligand, and one lattice water molecule. The Cu1 and O4 atoms lie on the crystallographic twofold axis, and the remaining atoms occupy general positions. The Cu²⁺ ion is coordinated to two oxygen atoms from two ligands and two nitrogen atoms from another two ligands to form a distorted square plane. The Cu1···O4 length (2.490 (3) Å), which is represented by a dotted line in Fig. 1, is extremely long, considering the covalent radii of Cu (1.28 Å) and O (0.66 Å) atoms. The van der Waals radii of Cu and O atoms are 1.40 and 1.52 Å, respectively, and therefore the Cu1···O4 bond may be best described as a strong van der Waals contact. Consequently, the coordination sphere of the Cu²⁺ ion may be thought of as square pyramidal, if the Cu1···O4 van der Waals contact is included. The molecular plane, defined by the two O and two N atoms, is extremely distorted from the planarity with the average atomic displacement of 0.328 (1) Å. Two carboxylate oxygen atoms act differently; one (O1) is coordinated to the Cu²⁺ ion and the other (O2) acts as a H-bond acceptor. The terminal carboxylate and pyridyl groups are bonded to the Cu²⁺ ions, indicating that this ligand behaves as a linking ligand. The amide group (–CONH–) does not coordinate to the metal ion, and the carbonyl oxygen (O3) acts as a H-bond acceptor and the N–H bond behaves as a H-bond donor. In fact, all of the hydrogen atoms in the amide group and lattice water molecule participate in the hydrogen bonds of the O–H···O or N–H···O types (Table 1). Fig. 2 shows a projection of the title polymer along the c-axis. The repeat unit consists of four ligands and four Cu²⁺ ions. This unit contains 56 atoms (4 Cu²⁺ ions and 52 ligand atoms) with the Cu²⁺···Cu²⁺ separation of 15.2045 (4) Å. The repeat units are connected by the ligands to form a 2-D layer in the [110] direction.

Related literature top

For coordination polymers based on linking ligands with O- and N-donor atoms, see: Robin & Fromm (2006). For d–f coordination polymers based on linking ligands with pyridyl–carboxylate terminal ligands, see: Hu et al. (2012); Chen et al. (2010); Tang et al. (2010); Yue et al. (2011); Zhu et al. (2010). For related potential linking ligands, see: Han & Lee (2012); Zheng & Lee (2012). For the ligand used for the preparation of the title compound, see: Song & Lee (2012).

Experimental top

A mixture of Cu(NO₃)₂^.3H₂O (48.3 mg, 0.2 mmol) and 6-(nicotinamido)-2-naphthoic acid (58.4 mg, 0.2 mmol) in H₂O (20 ml) was sealed in a 24 ml Teflon-lined vessel. The reaction mixture was heated 150 °C for 72 h and then slowly air-cooled to room temperature for 24 h. The resulting green crystals were isolated by filtration, washed by methanol (10 ml × 3), and then air-dried to give the title compound (19 mg, 0.027 mmol, 27% yield). mp: 586–589 K. IR (KBr, cm^-1): 3474 (w), 2897 (w), 2633 (w), 2383 (w), 2298 (w), 2084 (w), 1805 (w), 1660 (m), 1580 (m), 1483 (m), 1353 (m), 1204 (w), 1108 (w), 1049 (w), 951 (w), 886 (w), 824 (w), 772 (w), 749 (w), 702 (w), 625 (w), 457 (w).

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Bruker, 2008); software used to prepare material for publication: SHELXTL (Bruker, 2008).

Figures top

	Fig. 1. An asymmetric unit of the title compound showing the atomic numbering and 50% probability displacement ellipsoids.
	Fig. 2. Packing diagram of the title compound, showing a 2-D layer in the [110] direction. Dotted lines represent hydrogen bonds.

Poly[[aquabis[µ₂-6-(pyridine-3-carboxamido)naphthalene-2- carboxylato]copper(II)] dihydrate] top

Crystal data top

[Cu(C₁₇H₁₁N₂O₃)₂(H₂O)]·2H₂O	F(000) = 1444
M_r = 700.14	D_x = 1.549 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 3663 reflections
a = 29.6255 (8) Å	θ = 2.8–26.3°
b = 6.8582 (2) Å	µ = 0.79 mm⁻¹
c = 14.8264 (4) Å	T = 296 K
β = 94.728 (3)°	Block, green
V = 3002.14 (14) Å³	0.18 × 0.16 × 0.16 mm
Z = 4

Data collection top

Bruker APEXII CCD diffractometer	3705 independent reflections
Radiation source: sealed tube	2462 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.071
ϕ and ω scans	θ_max = 28.3°, θ_min = 1.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −38→39
T_min = 0.870, T_max = 0.884	k = −9→8
24367 measured reflections	l = −19→19

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.095	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ²(F_o²) + (0.0323P)² + 3.3539P] where P = (F_o² + 2F_c²)/3
3705 reflections	(Δ/σ)_max < 0.001
234 parameters	Δρ_max = 0.31 e Å⁻³
0 restraints	Δρ_min = −0.28 e Å⁻³

Crystal data top

[Cu(C₁₇H₁₁N₂O₃)₂(H₂O)]·2H₂O	V = 3002.14 (14) Å³
M_r = 700.14	Z = 4
Monoclinic, C2/c	Mo Kα radiation
a = 29.6255 (8) Å	µ = 0.79 mm⁻¹
b = 6.8582 (2) Å	T = 296 K
c = 14.8264 (4) Å	0.18 × 0.16 × 0.16 mm
β = 94.728 (3)°

Data collection top

Bruker APEXII CCD diffractometer	3705 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2462 reflections with I > 2σ(I)
T_min = 0.870, T_max = 0.884	R_int = 0.071
24367 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	0 restraints
wR(F²) = 0.095	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	Δρ_max = 0.31 e Å⁻³
3705 reflections	Δρ_min = −0.28 e Å⁻³
234 parameters

Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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	0.5000	0.15958 (7)	0.7500	0.02730 (14)
O1	0.43940 (5)	0.1123 (3)	0.69567 (11)	0.0339 (5)
O2	0.43602 (6)	−0.1766 (3)	0.76371 (12)	0.0404 (5)
O3	0.14263 (6)	0.0207 (3)	0.50325 (12)	0.0388 (5)
O4	0.5000	0.5226 (5)	0.7500	0.0458 (8)
O5	0.11363 (10)	0.3690 (4)	0.58013 (19)	0.0586 (7)
N1	0.15983 (7)	−0.2657 (4)	0.57653 (15)	0.0298 (5)
N2	0.02186 (6)	−0.2919 (3)	0.62447 (13)	0.0248 (5)
C1	0.41869 (8)	−0.0433 (4)	0.71535 (16)	0.0286 (6)
C2	0.36998 (8)	−0.0565 (4)	0.67842 (16)	0.0278 (6)
C3	0.34545 (8)	−0.2230 (4)	0.69110 (17)	0.0315 (6)
H3	0.3597	−0.3288	0.7207	0.038*
C4	0.29901 (8)	−0.2372 (4)	0.66017 (16)	0.0277 (6)
C5	0.27238 (8)	−0.4042 (4)	0.67428 (18)	0.0348 (7)
H5	0.2857	−0.5120	0.7037	0.042*
C6	0.22799 (8)	−0.4089 (4)	0.64557 (17)	0.0337 (6)
H6	0.2111	−0.5201	0.6555	0.040*
C7	0.20668 (8)	−0.2475 (4)	0.60056 (16)	0.0274 (6)
C8	0.23130 (8)	−0.0832 (4)	0.58502 (16)	0.0286 (6)
H8	0.2174	0.0225	0.5550	0.034*
C9	0.27774 (8)	−0.0746 (4)	0.61459 (16)	0.0269 (6)
C10	0.30397 (8)	0.0933 (4)	0.60178 (18)	0.0337 (7)
H10	0.2906	0.2001	0.5716	0.040*
C11	0.34869 (8)	0.1023 (4)	0.63273 (17)	0.0336 (7)
H11	0.3652	0.2148	0.6234	0.040*
C12	0.13114 (8)	−0.1337 (4)	0.53628 (16)	0.0268 (6)
C13	0.08218 (8)	−0.1870 (4)	0.53737 (16)	0.0247 (5)
C14	0.05252 (8)	−0.1765 (4)	0.45994 (16)	0.0295 (6)
H14	0.0624	−0.1341	0.4053	0.035*
C15	0.00809 (9)	−0.2305 (4)	0.46597 (17)	0.0329 (7)
H15	−0.0123	−0.2295	0.4147	0.040*
C16	−0.00604 (8)	−0.2859 (4)	0.54859 (16)	0.0292 (6)
H16	−0.0362	−0.3207	0.5518	0.035*
C17	0.06539 (8)	−0.2429 (4)	0.61731 (16)	0.0262 (6)
H17	0.0852	−0.2471	0.6692	0.031*
H1	0.1478 (10)	−0.368 (5)	0.588 (2)	0.055 (11)*
H4	0.4757 (10)	0.599 (6)	0.754 (3)	0.083 (13)*
H51	0.1036 (13)	0.338 (6)	0.623 (2)	0.072 (14)*
H52	0.1223 (14)	0.273 (7)	0.561 (3)	0.088 (17)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.0144 (2)	0.0424 (3)	0.0249 (2)	0.000	0.00091 (16)	0.000
O1	0.0186 (8)	0.0527 (14)	0.0301 (9)	−0.0109 (9)	0.0001 (7)	0.0015 (9)
O2	0.0268 (9)	0.0467 (14)	0.0464 (11)	0.0048 (10)	−0.0051 (8)	0.0007 (10)
O3	0.0274 (10)	0.0329 (12)	0.0565 (12)	−0.0030 (9)	0.0062 (9)	0.0119 (10)
O4	0.052 (2)	0.032 (2)	0.0547 (19)	0.000	0.0111 (16)	0.000
O5	0.0766 (18)	0.0398 (17)	0.0638 (17)	−0.0107 (13)	0.0319 (14)	−0.0065 (13)
N1	0.0185 (11)	0.0281 (14)	0.0426 (13)	−0.0052 (11)	0.0013 (9)	0.0033 (11)
N2	0.0186 (10)	0.0288 (14)	0.0269 (10)	0.0003 (9)	0.0015 (8)	−0.0006 (9)
C1	0.0190 (12)	0.0431 (19)	0.0237 (12)	−0.0003 (13)	0.0028 (10)	−0.0078 (12)
C2	0.0188 (12)	0.0366 (17)	0.0281 (13)	−0.0046 (12)	0.0028 (10)	−0.0042 (12)
C3	0.0233 (13)	0.0352 (18)	0.0356 (14)	0.0019 (12)	0.0003 (11)	0.0004 (12)
C4	0.0219 (12)	0.0310 (16)	0.0299 (13)	−0.0020 (12)	0.0001 (10)	−0.0020 (11)
C5	0.0260 (14)	0.0308 (17)	0.0467 (16)	−0.0020 (12)	−0.0024 (12)	0.0081 (13)
C6	0.0278 (14)	0.0278 (16)	0.0450 (15)	−0.0059 (12)	−0.0003 (12)	0.0078 (13)
C7	0.0177 (12)	0.0326 (16)	0.0317 (13)	−0.0017 (12)	0.0021 (10)	−0.0005 (12)
C8	0.0220 (12)	0.0290 (16)	0.0343 (13)	−0.0011 (12)	−0.0003 (10)	0.0041 (12)
C9	0.0228 (12)	0.0299 (16)	0.0278 (12)	−0.0038 (11)	0.0012 (10)	−0.0008 (11)
C10	0.0256 (13)	0.0307 (17)	0.0437 (15)	−0.0045 (12)	−0.0031 (11)	0.0074 (12)
C11	0.0256 (13)	0.0376 (19)	0.0372 (14)	−0.0094 (12)	0.0001 (11)	0.0040 (12)
C12	0.0205 (12)	0.0313 (17)	0.0289 (12)	−0.0009 (12)	0.0040 (10)	−0.0020 (12)
C13	0.0204 (12)	0.0205 (15)	0.0332 (13)	0.0012 (11)	0.0031 (10)	−0.0024 (11)
C14	0.0276 (13)	0.0322 (17)	0.0286 (12)	−0.0012 (13)	0.0024 (10)	0.0016 (12)
C15	0.0281 (14)	0.0411 (18)	0.0281 (13)	−0.0006 (12)	−0.0061 (11)	0.0007 (12)
C16	0.0188 (12)	0.0349 (18)	0.0336 (13)	−0.0014 (11)	0.0003 (10)	−0.0013 (11)
C17	0.0187 (12)	0.0330 (16)	0.0265 (12)	0.0013 (11)	−0.0007 (10)	−0.0003 (11)

Geometric parameters (Å, º) top

Cu1—O1	1.9337 (16)	C4—C9	1.424 (4)
Cu1—O1ⁱ	1.9337 (16)	C5—C6	1.349 (3)
Cu1—N2ⁱⁱ	2.0476 (19)	C5—H5	0.9300
Cu1—N2ⁱⁱⁱ	2.0476 (19)	C6—C7	1.414 (4)
O1—C1	1.277 (3)	C6—H6	0.9300
O2—C1	1.246 (3)	C7—C8	1.372 (4)
O3—C12	1.227 (3)	C8—C9	1.410 (3)
O4—H4	0.90 (3)	C8—H8	0.9300
O5—H51	0.75 (4)	C9—C10	1.410 (4)
O5—H52	0.77 (4)	C10—C11	1.367 (3)
N1—C12	1.347 (3)	C10—H10	0.9300
N1—C7	1.410 (3)	C11—H11	0.9300
N1—H1	0.81 (3)	C12—C13	1.497 (3)
N2—C16	1.341 (3)	C13—C17	1.377 (3)
N2—C17	1.345 (3)	C13—C14	1.389 (3)
N2—Cu1^iv	2.0476 (19)	C14—C15	1.377 (3)
C1—C2	1.503 (3)	C14—H14	0.9300
C2—C3	1.374 (4)	C15—C16	1.380 (3)
C2—C11	1.405 (4)	C15—H15	0.9300
C3—C4	1.417 (3)	C16—H16	0.9300
C3—H3	0.9300	C17—H17	0.9300
C4—C5	1.416 (4)

O1—Cu1—O1ⁱ	160.69 (12)	C8—C7—C6	120.0 (2)
O1—Cu1—N2ⁱⁱ	93.07 (7)	N1—C7—C6	116.2 (2)
O1ⁱ—Cu1—N2ⁱⁱ	90.06 (7)	C7—C8—C9	120.1 (2)
O1—Cu1—N2ⁱⁱⁱ	90.06 (7)	C7—C8—H8	120.0
O1ⁱ—Cu1—N2ⁱⁱⁱ	93.07 (7)	C9—C8—H8	120.0
N2ⁱⁱ—Cu1—N2ⁱⁱⁱ	161.31 (12)	C8—C9—C10	121.8 (2)
C1—O1—Cu1	119.48 (17)	C8—C9—C4	119.8 (2)
H51—O5—H52	104 (4)	C10—C9—C4	118.4 (2)
C12—N1—C7	128.7 (2)	C11—C10—C9	121.4 (3)
C12—N1—H1	114 (2)	C11—C10—H10	119.3
C7—N1—H1	118 (2)	C9—C10—H10	119.3
C16—N2—C17	117.1 (2)	C10—C11—C2	120.7 (3)
C16—N2—Cu1^iv	123.25 (15)	C10—C11—H11	119.6
C17—N2—Cu1^iv	119.30 (15)	C2—C11—H11	119.6
O2—C1—O1	124.2 (2)	O3—C12—N1	124.8 (2)
O2—C1—C2	120.2 (2)	O3—C12—C13	121.1 (2)
O1—C1—C2	115.6 (2)	N1—C12—C13	114.1 (2)
C3—C2—C11	119.3 (2)	C17—C13—C14	118.5 (2)
C3—C2—C1	120.2 (2)	C17—C13—C12	119.8 (2)
C11—C2—C1	120.5 (2)	C14—C13—C12	121.7 (2)
C2—C3—C4	121.5 (3)	C15—C14—C13	118.4 (2)
C2—C3—H3	119.2	C15—C14—H14	120.8
C4—C3—H3	119.2	C13—C14—H14	120.8
C5—C4—C3	123.1 (2)	C14—C15—C16	119.5 (2)
C5—C4—C9	118.3 (2)	C14—C15—H15	120.2
C3—C4—C9	118.7 (2)	C16—C15—H15	120.2
C6—C5—C4	120.9 (3)	N2—C16—C15	122.8 (2)
C6—C5—H5	119.6	N2—C16—H16	118.6
C4—C5—H5	119.6	C15—C16—H16	118.6
C5—C6—C7	121.0 (3)	N2—C17—C13	123.6 (2)
C5—C6—H6	119.5	N2—C17—H17	118.2
C7—C6—H6	119.5	C13—C17—H17	118.2
C8—C7—N1	123.8 (2)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O5^v	0.81 (3)	2.07 (3)	2.857 (4)	164 (3)
O5—H51···O2ⁱⁱ	0.75 (4)	2.13 (4)	2.861 (3)	164 (4)
O5—H52···O3	0.77 (4)	2.04 (4)	2.811 (4)	177 (5)
O4—H4···O2^vi	0.90 (3)	1.95 (3)	2.820 (3)	163 (3)

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

Experimental details

Crystal data
Chemical formula	[Cu(C₁₇H₁₁N₂O₃)₂(H₂O)]·2H₂O
M_r	700.14
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	296
a, b, c (Å)	29.6255 (8), 6.8582 (2), 14.8264 (4)
β (°)	94.728 (3)
V (Å³)	3002.14 (14)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.79
Crystal size (mm)	0.18 × 0.16 × 0.16

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.870, 0.884
No. of measured, independent and observed [I > 2σ(I)] reflections	24367, 3705, 2462
R_int	0.071
(sin θ/λ)_max (Å⁻¹)	0.667

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.095, 1.00
No. of reflections	3705
No. of parameters	234
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.31, −0.28

Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Bruker, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O5ⁱ	0.81 (3)	2.07 (3)	2.857 (4)	164 (3)
O5—H51···O2ⁱⁱ	0.75 (4)	2.13 (4)	2.861 (3)	164 (4)
O5—H52···O3	0.77 (4)	2.04 (4)	2.811 (4)	177 (5)
O4—H4···O2ⁱⁱⁱ	0.90 (3)	1.95 (3)	2.820 (3)	163 (3)

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

Acknowledgements

This research was supported by Basic Science Research Program through the National Research Foundation of Korea (NRF) funded by the Ministry of Education, Science and Technology (No. 2012R1A1A2000876).

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