catena-Poly[[[diaqua­bis(2-methyl-6-oxo-1,6-dihydro-3,4′-bipyridine-5-carbo­nitrile)copper(II)]-μ-sulfato] tetra­hydrate]

Niu, C.-Y.; Ning, A.-M.; Feng, C.-L.; Dang, Y.-L.; Kou, C.-H.

doi:10.1107/S1600536808038919

catena-Poly[[[diaquabis(2-methyl-6-oxo-1,6-dihydro-3,4′-bipyridine-5-carbonitrile)copper(II)]-μ-sulfato] tetrahydrate]

C.-Y. Niu, A.-M. Ning, C.-L. Feng, Y.-L. Dang and C.-H. Kou

In the title polymer, {[Cu(SO₄)(C₁₂H₉N₃O)₂(H₂O)₂]·4H₂O}_n, both the metal center and the sulfate anion are located on a twofold axis. The Cu^II ion is coordinated by two pyridyl N atoms from two symmetry-related organic ligands, two O atoms from two symmetry-related water molecules, and two O atoms from two symmetry-related sulfate anions, resulting in a distorted octahedral geometry. The sulfate anions act as μ₂-bridges and connect metal ions, forming a one-dimensional chain along the b axis. The three-dimensional crystal structure is established through intermolecular N—H

O and O—H

O hydrogen bonds involving the organic ligands, sulfate anions, coordinated and uncoordinated water molecules, and through π–π interacting 2-pyridone rings, with centroid–centroid separations of ca 3.96 Å and tilt angles of ca 2.62°.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536808038919/bh2204sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536808038919/bh2204Isup2.hkl Contains datablock I

CCDC reference: 665295

checkCIF report

Key indicators

Single-crystal X-ray study
T = 291 K
Mean (C-C) = 0.004 Å
R factor = 0.033
wR factor = 0.091
Data-to-parameter ratio = 13.7

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT417_ALERT_2_B Short Inter D-H..H-D       H5W    ..  H5W     ..       1.87 Ang.
PLAT420_ALERT_2_B D-H Without Acceptor       O6     -   H5W    ...          ?

Alert level C
            Value of measurement temperature given =   291.000
            Value of melting point given =     0.000
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Cu1    --  O4      ..       7.20 su
PLAT371_ALERT_2_C Long   C(sp2)-C(sp1) Bond  C8     -   C12    ...       1.44 Ang.
PLAT417_ALERT_2_C Short Inter D-H..H-D       H3W    ..  H5W     ..       2.11 Ang.
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent .....          ?
PLAT158_ALERT_4_C The Input Unitcell is NOT Standard/Reduced .....          ?
PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety        C11

   0 ALERT level A = In general: serious problem
   2 ALERT level B = Potentially serious problem
   6 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   5 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Comment top

The coordinating modes of sulfate anions can be µ₂, µ₃, and µ₄ bridges that have been used to construct metal-organic frameworks (Carlucci, et al., 2003; Xu, et al., 2003; Niu, et al., 2008).

In the title compound, (I), the central copper ion is coordinated by two N atoms from two symmetry-related organic ligands [N1, N1ⁱ; symmetry code: (i) -x + 3/2, -y + 3/2, z], two O atoms from two symmetry-related sulfate anions (O2, O2ⁱ), and two symmetry-related water O atoms (O4, O4ⁱ), forming a slightly distorted octahedral coordination environment (Fig. 1). The trans bond angles around metal centers are in the range 174.24 (9)–176.94 (8)°, close to 180 °, and the cis bond angles are in the range 86.58 (6)–93.50 (11) °, close to the right angle (Table 1).

Sulfate anions in the title compound act as µ₂-bridging ligands to connect copper ions together, forming a one-dimensional chain along b axis. The separation of two neighbouring copper atoms in one chain is about 6.85 Å. The organic molecules, 1,6-dihydro-2-methyl-6-oxo-(3,4'-bipyridine)-5-carbonitrile, act as terminal ligands, being coordinated to the copper atoms in chains only through pyridyl N atoms, with the other N and O atoms remaining uncoordinated (Fig. 2). The S1 atom of the sulfate anion is located on a special position of space group Pccn, bonding four symmetry-related oxygen atoms [O2, O2ⁱⁱ, O3, O3^ii; symmetry code: (ii) -x + 3/2, -y + 1/2, z]

There are hydrogen bonds involving organic ligands, sulfate anions, coordinated water molecules, and solvent water molecules. All O atoms of water molecules can either act as donors or as acceptors. Uncoordinating N atoms of pyridone rings only act as donors and sulfate O atoms as acceptors. Neighbouring chains are connected together by these hydrogen bonds (Fig. 3). In addition to these intermolecular hydrogen bonds, there are weak π-π interactions between parallel pyridone rings from two neighbouring chains, with centroid to centroid distances of about 3.96 Å and dihedral angles of about 2.62°.

Related literature top

For backgorung on metal-organic frameworks using sulfate ions as bridging ligands, see: Carlucci et al. (2003); Niu et al. (2008); Xu et al. (2003).

Experimental top

A solution of CuSO₄^.5H₂O (0.025 g, 0.1 mmol) in CH₃OH (10 ml) was added to a solution of 1,6-dihydro-2-methyl-6-oxo-(3,4'-bipyridine)-5-carbonitrile (0.021 g, 0.1 mmol) in CH₃OH (20 ml) under stirring. The mixture was filtered and the resulting solution allowed to evaporate slowly. About 40 days later, blue block single crystals suitable for X-ray analysis were obtained (yield: ca. 35%).

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); program(s) used to solve structure: SHELXL97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2005); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. A view of the Cu^II coordination environment in the polymeric structure of (I), showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level. All H atoms and solvent water molecules are omitted for clarity. [Symmetry codes: (i) -x + 3/2, -y + 3/2, z; (ii) -x + 3/2, -y + 1/2, z].
	Fig. 2. A ball-stick diagram showing the one-dimensional chain. All water molecules and H atoms have been omitted for clarity.
	Fig. 3. A diagram showing the intermolecular hydrogen bonds indicated by dashed lines.

catena-Poly[[[diaquabis(2-methyl-6-oxo-1,6-dihydro-3,4'-bipyridine-5- carbonitrile)copper(II)]-µ-sulfato] tetrahydrate] top

Crystal data top

[Cu(SO₄)(C₁₂H₉N₃O)₂(H₂O)₂]·4H₂O	F(000) = 1428
M_r = 690.14	D_x = 1.554 Mg m⁻³
Orthorhombic, Pccn	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ab 2ac	Cell parameters from 3682 reflections
a = 21.672 (3) Å	θ = 2.3–25.8°
b = 6.8533 (8) Å	µ = 0.88 mm⁻¹
c = 19.860 (3) Å	T = 291 K
V = 2949.8 (6) Å³	Block, blue
Z = 4	0.32 × 0.23 × 0.22 mm

Data collection top

Siemens SMART CCD area-detector diffractometer	2751 independent reflections
Radiation source: fine-focus sealed tube	2195 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.034
ϕ and ω scans	θ_max = 25.5°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Siemens, 1996)	h = −23→26
T_min = 0.764, T_max = 0.828	k = −8→8
14282 measured reflections	l = −24→24

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) = 0.091	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0412P)² + 2.9734P] where P = (F_o² + 2F_c²)/3
2751 reflections	(Δ/σ)_max = 0.001
201 parameters	Δρ_max = 0.43 e Å⁻³
0 restraints	Δρ_min = −0.41 e Å⁻³

Crystal data top

[Cu(SO₄)(C₁₂H₉N₃O)₂(H₂O)₂]·4H₂O	V = 2949.8 (6) Å³
M_r = 690.14	Z = 4
Orthorhombic, Pccn	Mo Kα radiation
a = 21.672 (3) Å	µ = 0.88 mm⁻¹
b = 6.8533 (8) Å	T = 291 K
c = 19.860 (3) Å	0.32 × 0.23 × 0.22 mm

Data collection top

Siemens SMART CCD area-detector diffractometer	2751 independent reflections
Absorption correction: multi-scan (SADABS; Siemens, 1996)	2195 reflections with I > 2σ(I)
T_min = 0.764, T_max = 0.828	R_int = 0.034
14282 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.033	0 restraints
wR(F²) = 0.091	H-atom parameters constrained
S = 1.03	Δρ_max = 0.43 e Å⁻³
2751 reflections	Δρ_min = −0.41 e Å⁻³
201 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Cu1	0.7500	0.7500	0.559997 (19)	0.02153 (13)
S1	0.7500	0.2500	0.60744 (4)	0.02089 (19)
O1	0.39746 (9)	0.8422 (3)	0.20721 (9)	0.0447 (5)
O2	0.73015 (9)	0.4141 (3)	0.56593 (9)	0.0336 (4)
O3	0.69854 (8)	0.1865 (3)	0.65199 (9)	0.0321 (4)
O4	0.68578 (8)	0.7952 (2)	0.63128 (9)	0.0291 (4)
H1W	0.6886	0.9077	0.6453	0.044*
H2W	0.6925	0.7125	0.6601	0.044*
O5	0.69067 (10)	0.5382 (3)	0.73479 (10)	0.0464 (5)
H3W	0.7171	0.5327	0.7654	0.070*
H4W	0.6888	0.4332	0.7139	0.070*
O6	0.78398 (17)	0.0151 (9)	0.32780 (19)	0.183 (3)
H5W	0.7713	0.1316	0.3329	0.275*
H6W	0.8145	0.0156	0.3023	0.275*
N1	0.68294 (9)	0.7831 (3)	0.49032 (10)	0.0250 (5)
N2	0.42947 (9)	0.8330 (3)	0.31661 (10)	0.0282 (5)
H2D	0.3915	0.8317	0.3292	0.034*
N3	0.52884 (13)	0.8349 (4)	0.10367 (12)	0.0514 (7)
C1	0.67866 (13)	0.9364 (4)	0.44882 (13)	0.0357 (7)
H1	0.7090	1.0323	0.4509	0.043*
C2	0.63105 (12)	0.9583 (4)	0.40299 (14)	0.0371 (7)
H2	0.6300	1.0665	0.3747	0.044*
C3	0.58505 (11)	0.8190 (4)	0.39931 (12)	0.0268 (5)
C4	0.58919 (13)	0.6623 (4)	0.44327 (14)	0.0392 (7)
H4A	0.5590	0.5659	0.4430	0.047*
C5	0.63819 (12)	0.6500 (4)	0.48731 (14)	0.0374 (7)
H5	0.6401	0.5437	0.5163	0.045*
C6	0.53443 (11)	0.8312 (4)	0.34882 (12)	0.0260 (5)
C7	0.54932 (11)	0.8372 (4)	0.27966 (12)	0.0265 (5)
H7	0.5906	0.8407	0.2670	0.032*
C8	0.50482 (11)	0.8381 (4)	0.23072 (11)	0.0269 (5)
C9	0.44027 (11)	0.8380 (4)	0.24792 (12)	0.0280 (6)
C10	0.47276 (11)	0.8298 (4)	0.36634 (12)	0.0270 (5)
C11	0.44750 (13)	0.8324 (5)	0.43639 (13)	0.0405 (7)
H11A	0.4237	0.9490	0.4430	0.061*
H11B	0.4809	0.8295	0.4681	0.061*
H11C	0.4216	0.7204	0.4431	0.061*
C12	0.51933 (12)	0.8364 (4)	0.16012 (13)	0.0318 (6)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.0154 (2)	0.0276 (2)	0.0216 (2)	−0.00008 (18)	0.000	0.000
S1	0.0153 (4)	0.0200 (4)	0.0273 (4)	0.0008 (4)	0.000	0.000
O1	0.0265 (10)	0.0688 (15)	0.0387 (10)	0.0036 (10)	−0.0118 (9)	−0.0038 (10)
O2	0.0356 (10)	0.0244 (10)	0.0408 (10)	−0.0002 (8)	−0.0124 (8)	0.0060 (8)
O3	0.0225 (9)	0.0322 (10)	0.0417 (10)	−0.0012 (8)	0.0090 (8)	−0.0015 (8)
O4	0.0268 (10)	0.0271 (9)	0.0335 (9)	−0.0005 (7)	0.0046 (8)	0.0011 (7)
O5	0.0499 (13)	0.0423 (12)	0.0469 (12)	0.0064 (10)	0.0111 (10)	−0.0005 (9)
O6	0.073 (2)	0.360 (8)	0.116 (3)	−0.085 (4)	−0.016 (2)	0.094 (4)
N1	0.0171 (10)	0.0333 (12)	0.0245 (10)	−0.0016 (9)	−0.0005 (8)	0.0027 (9)
N2	0.0143 (10)	0.0381 (12)	0.0323 (11)	0.0005 (10)	0.0005 (8)	−0.0017 (10)
N3	0.0542 (17)	0.0684 (19)	0.0316 (14)	0.0124 (15)	0.0024 (12)	0.0037 (13)
C1	0.0284 (15)	0.0395 (16)	0.0393 (15)	−0.0127 (13)	−0.0094 (12)	0.0105 (12)
C2	0.0317 (15)	0.0414 (16)	0.0382 (15)	−0.0090 (13)	−0.0098 (12)	0.0167 (12)
C3	0.0186 (12)	0.0360 (14)	0.0260 (12)	0.0003 (11)	−0.0011 (10)	0.0009 (11)
C4	0.0291 (15)	0.0370 (15)	0.0516 (17)	−0.0134 (13)	−0.0144 (13)	0.0133 (14)
C5	0.0294 (15)	0.0379 (16)	0.0451 (15)	−0.0084 (13)	−0.0117 (12)	0.0156 (13)
C6	0.0208 (13)	0.0299 (13)	0.0274 (12)	−0.0020 (11)	−0.0042 (10)	0.0029 (11)
C7	0.0172 (12)	0.0298 (13)	0.0325 (13)	0.0002 (11)	−0.0013 (10)	0.0044 (11)
C8	0.0252 (13)	0.0289 (13)	0.0265 (12)	0.0016 (11)	0.0000 (10)	0.0018 (10)
C9	0.0229 (13)	0.0302 (14)	0.0309 (13)	0.0004 (11)	−0.0040 (11)	−0.0013 (11)
C10	0.0220 (13)	0.0307 (13)	0.0284 (12)	−0.0008 (11)	−0.0019 (10)	0.0005 (11)
C11	0.0299 (15)	0.0608 (19)	0.0309 (14)	−0.0027 (15)	0.0027 (11)	−0.0016 (14)
C12	0.0278 (14)	0.0343 (15)	0.0333 (15)	0.0037 (12)	−0.0023 (11)	0.0031 (12)

Geometric parameters (Å, º) top

Cu1—O4ⁱ	2.0093 (17)	N2—H2D	0.8600
Cu1—O4	2.0093 (17)	N3—C12	1.140 (3)
Cu1—N1	2.0197 (19)	C1—C2	1.384 (4)
Cu1—N1ⁱ	2.0197 (19)	C1—H1	0.9300
Cu1—O2	2.3450 (18)	C2—C3	1.382 (4)
Cu1—O2ⁱ	2.3450 (18)	C2—H2	0.9300
S1—O2	1.4592 (17)	C3—C4	1.387 (4)
S1—O2ⁱⁱ	1.4592 (17)	C3—C6	1.489 (3)
S1—O3ⁱⁱ	1.4885 (17)	C4—C5	1.378 (4)
S1—O3	1.4885 (17)	C4—H4A	0.9300
O1—C9	1.231 (3)	C5—H5	0.9300
O4—H1W	0.8217	C6—C10	1.381 (3)
O4—H2W	0.8188	C6—C7	1.412 (3)
O5—H3W	0.8349	C7—C8	1.369 (3)
O5—H4W	0.8320	C7—H7	0.9300
O6—H5W	0.8509	C8—C12	1.437 (4)
O6—H6W	0.8326	C8—C9	1.440 (3)
N1—C5	1.333 (3)	C10—C11	1.495 (3)
N1—C1	1.339 (3)	C11—H11A	0.9600
N2—C10	1.363 (3)	C11—H11B	0.9600
N2—C9	1.385 (3)	C11—H11C	0.9600

O4ⁱ—Cu1—O4	90.42 (10)	C2—C1—H1	118.6
O4ⁱ—Cu1—N1	176.94 (7)	C3—C2—C1	119.9 (2)
O4—Cu1—N1	88.10 (8)	C3—C2—H2	120.1
O4ⁱ—Cu1—N1ⁱ	88.10 (8)	C1—C2—H2	120.1
O4—Cu1—N1ⁱ	176.94 (8)	C2—C3—C4	117.0 (2)
N1—Cu1—N1ⁱ	93.50 (11)	C2—C3—C6	121.9 (2)
O4ⁱ—Cu1—O2	86.57 (6)	C4—C3—C6	121.0 (2)
O4—Cu1—O2	89.37 (7)	C5—C4—C3	119.8 (3)
N1—Cu1—O2	90.73 (7)	C5—C4—H4A	120.1
N1ⁱ—Cu1—O2	93.21 (8)	C3—C4—H4A	120.1
O4ⁱ—Cu1—O2ⁱ	89.37 (7)	N1—C5—C4	123.2 (2)
O4—Cu1—O2ⁱ	86.58 (6)	N1—C5—H5	118.4
N1—Cu1—O2ⁱ	93.21 (8)	C4—C5—H5	118.4
N1ⁱ—Cu1—O2ⁱ	90.73 (7)	C10—C6—C7	117.8 (2)
O2—Cu1—O2ⁱ	174.24 (9)	C10—C6—C3	122.9 (2)
O2—S1—O2ⁱⁱ	111.21 (15)	C7—C6—C3	119.2 (2)
O2—S1—O3ⁱⁱ	109.36 (10)	C8—C7—C6	122.0 (2)
O2ⁱⁱ—S1—O3ⁱⁱ	109.88 (10)	C8—C7—H7	119.0
O2—S1—O3	109.88 (10)	C6—C7—H7	119.0
O2ⁱⁱ—S1—O3	109.37 (10)	C7—C8—C12	122.6 (2)
O3ⁱⁱ—S1—O3	107.06 (15)	C7—C8—C9	121.1 (2)
S1—O2—Cu1	136.96 (10)	C12—C8—C9	116.4 (2)
Cu1—O4—H1W	109.4	O1—C9—N2	121.3 (2)
Cu1—O4—H2W	105.3	O1—C9—C8	125.2 (2)
H1W—O4—H2W	113.6	N2—C9—C8	113.5 (2)
H3W—O5—H4W	110.9	N2—C10—C6	118.9 (2)
H5W—O6—H6W	108.9	N2—C10—C11	115.0 (2)
C5—N1—C1	117.3 (2)	C6—C10—C11	126.1 (2)
C5—N1—Cu1	118.51 (17)	C10—C11—H11A	109.5
C1—N1—Cu1	124.06 (17)	C10—C11—H11B	109.5
C10—N2—C9	126.7 (2)	H11A—C11—H11B	109.5
C10—N2—H2D	116.6	C10—C11—H11C	109.5
C9—N2—H2D	116.6	H11A—C11—H11C	109.5
N1—C1—C2	122.8 (2)	H11B—C11—H11C	109.5
N1—C1—H1	118.6	N3—C12—C8	177.8 (3)

O2ⁱⁱ—S1—O2—Cu1	−130.08 (19)	Cu1—N1—C5—C4	177.7 (2)
O3ⁱⁱ—S1—O2—Cu1	−8.6 (2)	C3—C4—C5—N1	0.1 (5)
O3—S1—O2—Cu1	108.69 (16)	C2—C3—C6—C10	−124.4 (3)
O4ⁱ—Cu1—O2—S1	6.07 (17)	C4—C3—C6—C10	58.0 (4)
O4—Cu1—O2—S1	−84.39 (17)	C2—C3—C6—C7	58.1 (4)
N1—Cu1—O2—S1	−172.48 (17)	C4—C3—C6—C7	−119.5 (3)
N1ⁱ—Cu1—O2—S1	93.97 (17)	C10—C6—C7—C8	−1.2 (4)
O4—Cu1—N1—C5	−66.4 (2)	C3—C6—C7—C8	176.5 (3)
N1ⁱ—Cu1—N1—C5	116.2 (2)	C6—C7—C8—C12	−177.5 (2)
O2—Cu1—N1—C5	22.9 (2)	C6—C7—C8—C9	1.6 (4)
O2ⁱ—Cu1—N1—C5	−152.9 (2)	C10—N2—C9—O1	−179.4 (3)
O4—Cu1—N1—C1	110.0 (2)	C10—N2—C9—C8	0.5 (4)
N1ⁱ—Cu1—N1—C1	−67.4 (2)	C7—C8—C9—O1	178.7 (3)
O2—Cu1—N1—C1	−160.6 (2)	C12—C8—C9—O1	−2.2 (4)
O2ⁱ—Cu1—N1—C1	23.5 (2)	C7—C8—C9—N2	−1.2 (4)
C5—N1—C1—C2	−1.4 (4)	C12—C8—C9—N2	177.9 (2)
Cu1—N1—C1—C2	−177.9 (2)	C9—N2—C10—C6	−0.2 (4)
N1—C1—C2—C3	0.6 (5)	C9—N2—C10—C11	177.7 (3)
C1—C2—C3—C4	0.5 (4)	C7—C6—C10—N2	0.4 (4)
C1—C2—C3—C6	−177.2 (3)	C3—C6—C10—N2	−177.2 (2)
C2—C3—C4—C5	−0.8 (4)	C7—C6—C10—C11	−177.2 (3)
C6—C3—C4—C5	176.9 (3)	C3—C6—C10—C11	5.2 (5)
C1—N1—C5—C4	1.0 (4)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2D···O3ⁱⁱⁱ	0.86	1.99	2.847 (3)	173
O4—H2W···O5	0.82	1.90	2.709 (3)	167
O5—H4W···O3	0.83	2.10	2.922 (3)	170
O4—H1W···O3^iv	0.82	1.93	2.727 (2)	164
O5—H3W···O6^v	0.83	1.94	2.763 (4)	171
O6—H6W···O1^vi	0.83	2.05	2.737 (4)	139

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

Experimental details

Crystal data
Chemical formula	[Cu(SO₄)(C₁₂H₉N₃O)₂(H₂O)₂]·4H₂O
M_r	690.14
Crystal system, space group	Orthorhombic, Pccn
Temperature (K)	291
a, b, c (Å)	21.672 (3), 6.8533 (8), 19.860 (3)
V (Å³)	2949.8 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.88
Crystal size (mm)	0.32 × 0.23 × 0.22

Data collection
Diffractometer	Siemens SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Siemens, 1996)
T_min, T_max	0.764, 0.828
No. of measured, independent and observed [I > 2σ(I)] reflections	14282, 2751, 2195
R_int	0.034
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.033, 0.091, 1.03
No. of reflections	2751
No. of parameters	201
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.43, −0.41

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg, 2005).

Selected geometric parameters (Å, º) top

Cu1—O4ⁱ	2.0093 (17)	Cu1—N1ⁱ	2.0197 (19)
Cu1—O4	2.0093 (17)	Cu1—O2	2.3450 (18)
Cu1—N1	2.0197 (19)	Cu1—O2ⁱ	2.3450 (18)

O4ⁱ—Cu1—O4	90.42 (10)	N1—Cu1—O2	90.73 (7)
O4ⁱ—Cu1—N1	176.94 (7)	N1ⁱ—Cu1—O2	93.21 (8)
O4—Cu1—N1	88.10 (8)	O4ⁱ—Cu1—O2ⁱ	89.37 (7)
O4ⁱ—Cu1—N1ⁱ	88.10 (8)	O4—Cu1—O2ⁱ	86.58 (6)
O4—Cu1—N1ⁱ	176.94 (8)	N1—Cu1—O2ⁱ	93.21 (8)
N1—Cu1—N1ⁱ	93.50 (11)	N1ⁱ—Cu1—O2ⁱ	90.73 (7)
O4ⁱ—Cu1—O2	86.57 (6)	O2—Cu1—O2ⁱ	174.24 (9)
O4—Cu1—O2	89.37 (7)

Symmetry code: (i) −x+3/2, −y+3/2, z.