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In the title complex, {[Cu(C4H5O4N)(C10H9N3)]·H2O}n, the Cu atom has a distorted CuO2N3 square-pyramidal geometry formed by an N,O-bidentate aspartate (asp) anion and an N,N-bidentate 2,2′-bipyridylamine (bpa) mol­ecule in the basal positions, and an O-monodentate asp ligand in the apical site. The complex forms a polymeric chain in which each metal centre is bridged to the next one by the asp anion. The crystal structure is stabilized by O—H...O and N—H...O hydrogen bonds and π–π stacking inter­actions involving the bpa ligands [centroid–centroid separation = 3.699 (4) Å].

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807043905/hb2533sup1.cif
Contains datablocks General, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807043905/hb2533Isup2.hkl
Contains datablock I

CCDC reference: 663589

Key indicators

  • Single-crystal X-ray study
  • T = 123 K
  • Mean [sigma](C-C) = 0.006 Å
  • R factor = 0.040
  • wR factor = 0.079
  • Data-to-parameter ratio = 15.5

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT417_ALERT_2_C Short Inter D-H..H-D H10 .. H16 .. 2.10 Ang. PLAT764_ALERT_4_C Overcomplete CIF Bond List Detected (Rep/Expd) . 1.15 Ratio
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 27.48 From the CIF: _reflns_number_total 3469 Count of symmetry unique reflns 2010 Completeness (_total/calc) 172.59% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 1459 Fraction of Friedel pairs measured 0.726 Are heavy atom types Z>Si present yes PLAT791_ALERT_1_G Confirm the Absolute Configuration of C12 = . S PLAT794_ALERT_5_G Check Predicted Bond Valency for Cu1 (2) 2.29
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 3 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 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 1 ALERT type 5 Informative message, check

Comment top

Recently, significant attention has focused on Cu(II) complexes in the studies of their antitumor and/or antiviral activity (Wang & Okabe, 2005; Kelland, 2005).

As part of our ongoing studies (Yodoshi et al., 2007) of mixed-ligand copper complexes, we now report the synthesis and structure of the title compound, (I), containing both aspartate (asp) anions and 2,2'-bipyridylamine (bpa) molecules (Fig. 1).

The Cu atom in (I) has a distorted square-pyramidal geometry formed by one O atom of the α-carboxylate group, one N atom of the α-amino group of an aspartate anion and two N atoms of a bidentate bpa in the basal plane and one O atom from the β-carboxylate of an aspartate in the axial position. Each complex is bridged through the O atom in the axial position, and forms polymeric chains.

Cu1 deviates by 0.289 (1) Å from the mean plane through atoms N1, N2, N4 and O1. A six-membered chelate ring Cu1/N1/C5/N3/C6/N2 and a five- membered one Cu1/O1/C11/C12/N4 are formed between the Cu1 atom and the bpa and asp ligands, respectively, where the dihedral angle between two planes, Cu1/N1/N2 and Cu1/O1/N4 is 23.1 (2)°. The two pyridine rings in the bpa ligand are also non-planar with the dihedral angle of 23.15 (8)°.

The metal coordination in (I) resembles that in monomeric Cu(asp)(bpy)H2O (Antolini et al., 1983), and the polymeric linear chain structure of (I) resembles that in [Cu(glu)(bpy)]n (Antolini et al., 1985).

The bond distances (Table 1) in the square plane in (I) are similar to those in Cu(asp)(bpy)H2O and [Cu(glu)(bpy)]n. The Cu1—O3 bond lenght is a little longer than those in the square plane because of the well known Jahn-Teller effect. The axial distance is similar to that in the polymeric complex, {Cu(glu)(bpy)]n, but a little shorter than that in Cu(asp)(bpy)H2O.

The crystal structure of (I) is stabilized by O—H···O hydrogen bonds the water molecules and the carboxylate group of asp, and N—H···O hydrogen bonds between the imino group of bpa and the carboxylate group (Table 2). Aromatic π-π stacking interactions between bpa ligands of adjacent chains also stabilizes the crystal packing (Fig. 2). The distance between the centroids of the pyridine rings Cg1 (N1/C1—C5) and Cg2 (N2/C6—C10) (symmetry code: -1/2 + x, 1/2 - y, 1 - z) is 3.699 (4) Å (Spek, 2003).

Related literature top

For related structures, see: Antolini et al. (1983, 1985). For background, see: Kelland (2005); Wang & Okabe (2005); Yodoshi et al. (2007).

Experimental top

Bpa (50.0 mg) was mixed with CuCl2.2H2O (49.8 mg), in 5 ml of 80% (v/v) methanol-water solution for 5 min at room temperature (molar ratio 1:1). The aquamarine-colored precipitate was dried under a vacuum and assumed to be [Cu(bpa)Cl2]. Then, the precipitate (5.0 mg) was reacted with aspartic acid (2.0 mg) in 2.4 ml dimethylsulfoxide for 60 min at 343 K. The reaction mixture was left to stand at room temperature, and after two months, blue needles of (I) appeared from the mother liquor.

Refinement top

The water H atoms were located in a difference map and refined as riding in their as-found relative positions with Uiso(H) = 1.5Ueq(O).

The other H atoms were located in a difference map, relocated in idealized locations (C—H = 0.93–0.97 Å, N—H = 0.86 Å) and refined as riding with Uiso(H) = 1.2Ueq(C, N)

Structure description top

Recently, significant attention has focused on Cu(II) complexes in the studies of their antitumor and/or antiviral activity (Wang & Okabe, 2005; Kelland, 2005).

As part of our ongoing studies (Yodoshi et al., 2007) of mixed-ligand copper complexes, we now report the synthesis and structure of the title compound, (I), containing both aspartate (asp) anions and 2,2'-bipyridylamine (bpa) molecules (Fig. 1).

The Cu atom in (I) has a distorted square-pyramidal geometry formed by one O atom of the α-carboxylate group, one N atom of the α-amino group of an aspartate anion and two N atoms of a bidentate bpa in the basal plane and one O atom from the β-carboxylate of an aspartate in the axial position. Each complex is bridged through the O atom in the axial position, and forms polymeric chains.

Cu1 deviates by 0.289 (1) Å from the mean plane through atoms N1, N2, N4 and O1. A six-membered chelate ring Cu1/N1/C5/N3/C6/N2 and a five- membered one Cu1/O1/C11/C12/N4 are formed between the Cu1 atom and the bpa and asp ligands, respectively, where the dihedral angle between two planes, Cu1/N1/N2 and Cu1/O1/N4 is 23.1 (2)°. The two pyridine rings in the bpa ligand are also non-planar with the dihedral angle of 23.15 (8)°.

The metal coordination in (I) resembles that in monomeric Cu(asp)(bpy)H2O (Antolini et al., 1983), and the polymeric linear chain structure of (I) resembles that in [Cu(glu)(bpy)]n (Antolini et al., 1985).

The bond distances (Table 1) in the square plane in (I) are similar to those in Cu(asp)(bpy)H2O and [Cu(glu)(bpy)]n. The Cu1—O3 bond lenght is a little longer than those in the square plane because of the well known Jahn-Teller effect. The axial distance is similar to that in the polymeric complex, {Cu(glu)(bpy)]n, but a little shorter than that in Cu(asp)(bpy)H2O.

The crystal structure of (I) is stabilized by O—H···O hydrogen bonds the water molecules and the carboxylate group of asp, and N—H···O hydrogen bonds between the imino group of bpa and the carboxylate group (Table 2). Aromatic π-π stacking interactions between bpa ligands of adjacent chains also stabilizes the crystal packing (Fig. 2). The distance between the centroids of the pyridine rings Cg1 (N1/C1—C5) and Cg2 (N2/C6—C10) (symmetry code: -1/2 + x, 1/2 - y, 1 - z) is 3.699 (4) Å (Spek, 2003).

For related structures, see: Antolini et al. (1983, 1985). For background, see: Kelland (2005); Wang & Okabe (2005); Yodoshi et al. (2007).

Computing details top

Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO (Rigaku, 1998); data reduction: CrystalStructure (Rigaku/MSC, 2005) and CRYSTALS (Betteridge et al., 2003); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2003); software used to prepare material for publication: CrystalStructure (Rigaku/MSC, 2005).

Figures top
[Figure 1] Fig. 1. The asymmetric unit of (I) expanded to show the polymeric connectivity with displacement ellipsoids shown at the 50% probability level (arbitrary spheres for the H atoms). The uncoordinated water molecule is omitted for clarity. Symmetry codes: (i) 1 + x, y, z; (ii) -1 + x, y, z.
[Figure 2] Fig. 2. A view of the hydrogen bonding (blue dashed lines) and π-π stacking (purple dashed lines) interactions in (I). See the text for the designations of Cg1 and Cg2 [at (-1/2 + x, 1/2 - y, 1 - z)]. Symmetry codes: (i) x + 1/2, -y + 1/2, -z + 1; (ii) -x, y + 1/2, -z + 3/2.
catena-Poly[[[(2,2'-bipyridylamine-κ2N,N')copper(II)]- µ2-L-aspartate-κ3O,N:O'] monohydrate] top
Crystal data top
[Cu(C4H5O4N)(C10H9N3)]·H2OF(000) = 788.00
Mr = 383.86Dx = 1.692 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.7107 Å
Hall symbol: P 2ac 2abCell parameters from 11236 reflections
a = 7.018 (5) Åθ = 3.1–27.5°
b = 10.364 (8) ŵ = 1.48 mm1
c = 20.72 (2) ÅT = 123 K
V = 1507 (2) Å3Needle, blue
Z = 40.40 × 0.04 × 0.04 mm
Data collection top
Rigaku R-AXIS RAPID
diffractometer
2022 reflections with F2 > 2.0σ(F2)
Detector resolution: 10.00 pixels mm-1Rint = 0.061
ω scansθmax = 27.5°
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)
h = 98
Tmin = 0.931, Tmax = 0.942k = 1313
13783 measured reflectionsl = 2626
3469 independent reflections
Refinement top
Refinement on F2 w = 1/[σ2(Fo2) + (0.0362P)2]
where P = (Fo2 + 2Fc2)/3
R[F2 > 2σ(F2)] = 0.040(Δ/σ)max < 0.001
wR(F2) = 0.079Δρmax = 0.85 e Å3
S = 0.94Δρmin = 0.90 e Å3
3469 reflectionsAbsolute structure: Flack (1983), 1416 Friedel pairs
224 parametersAbsolute structure parameter: 0.02 (2)
H-atom parameters constrained
Crystal data top
[Cu(C4H5O4N)(C10H9N3)]·H2OV = 1507 (2) Å3
Mr = 383.86Z = 4
Orthorhombic, P212121Mo Kα radiation
a = 7.018 (5) ŵ = 1.48 mm1
b = 10.364 (8) ÅT = 123 K
c = 20.72 (2) Å0.40 × 0.04 × 0.04 mm
Data collection top
Rigaku R-AXIS RAPID
diffractometer
3469 independent reflections
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)
2022 reflections with F2 > 2.0σ(F2)
Tmin = 0.931, Tmax = 0.942Rint = 0.061
13783 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.040H-atom parameters constrained
wR(F2) = 0.079Δρmax = 0.85 e Å3
S = 0.94Δρmin = 0.90 e Å3
3469 reflectionsAbsolute structure: Flack (1983), 1416 Friedel pairs
224 parametersAbsolute structure parameter: 0.02 (2)
Special details top

Geometry. ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY

Refinement. Refinement using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F2. R-factor (gt) are based on F. The threshold expression of F2 > 2.0 σ(F2) is used only for calculating R-factor (gt).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cu10.36399 (6)0.09559 (4)0.61800 (2)0.0172 (1)
O10.2334 (3)0.0709 (2)0.6236 (1)0.0242 (6)
O20.0185 (4)0.1830 (3)0.6789 (1)0.0292 (7)
O30.4093 (3)0.0429 (2)0.6832 (1)0.0209 (6)
O40.1666 (4)0.1431 (3)0.6343 (1)0.0297 (7)
O50.3663 (4)0.2681 (2)0.8106 (1)0.0279 (6)
N10.4276 (4)0.2784 (3)0.5966 (1)0.0168 (7)
N20.4572 (4)0.0421 (3)0.5318 (1)0.0178 (7)
N30.3895 (4)0.2443 (3)0.4851 (1)0.0197 (7)
N40.1925 (4)0.1424 (3)0.6924 (1)0.0177 (7)
C10.4647 (5)0.3616 (4)0.6454 (2)0.0209 (9)
C20.4876 (5)0.4911 (4)0.6369 (2)0.025 (1)
C30.4779 (5)0.5399 (4)0.5744 (2)0.0248 (9)
C40.4460 (5)0.4572 (4)0.5240 (2)0.0250 (9)
C50.4214 (5)0.3259 (3)0.5365 (2)0.0162 (8)
C60.4331 (5)0.1137 (4)0.4789 (2)0.0193 (8)
C70.4491 (5)0.0626 (4)0.4165 (2)0.0230 (9)
C80.4944 (5)0.0649 (4)0.4100 (2)0.0271 (9)
C90.5273 (5)0.1404 (4)0.4643 (2)0.0250 (9)
C100.5064 (5)0.0835 (4)0.5240 (2)0.0235 (8)
C110.1157 (5)0.0845 (3)0.6693 (2)0.0213 (8)
C120.0989 (5)0.0253 (3)0.7183 (2)0.0174 (8)
C130.1098 (5)0.0490 (3)0.7371 (2)0.0178 (8)
C140.2371 (5)0.0801 (4)0.6797 (2)0.0189 (8)
H10.47500.32860.68700.025*
H20.50910.54540.67190.030*
H30.49300.62780.56700.030*
H40.44070.48820.48190.030*
H50.42940.11430.38040.028*
H60.50340.10130.36910.033*
H70.56220.22660.46050.030*
H80.52710.13350.56050.028*
H90.33510.27890.45220.024*
H100.26150.18040.72370.021*
H110.10340.19880.67900.021*
H120.16780.00070.75740.021*
H130.15880.02720.75860.021*
H140.11530.12000.76750.021*
H150.40610.34240.81390.042*
H160.24800.27630.81310.042*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cu10.0183 (2)0.0164 (2)0.0169 (2)0.0009 (2)0.0007 (2)0.0000 (2)
O10.024 (1)0.021 (1)0.028 (2)0.005 (1)0.010 (1)0.002 (1)
O20.029 (2)0.017 (1)0.042 (2)0.002 (1)0.009 (1)0.001 (1)
O30.017 (1)0.024 (1)0.022 (1)0.002 (1)0.001 (1)0.004 (1)
O40.023 (1)0.046 (2)0.021 (2)0.006 (1)0.000 (1)0.018 (1)
O50.027 (1)0.019 (1)0.038 (2)0.002 (2)0.002 (2)0.005 (1)
N10.015 (1)0.018 (2)0.018 (2)0.002 (1)0.001 (1)0.001 (1)
N20.021 (2)0.018 (2)0.014 (2)0.003 (1)0.000 (1)0.002 (1)
N30.023 (2)0.020 (2)0.015 (2)0.001 (2)0.005 (1)0.004 (1)
N40.015 (1)0.017 (2)0.021 (2)0.002 (1)0.001 (1)0.003 (1)
C10.017 (2)0.025 (2)0.020 (2)0.002 (2)0.001 (2)0.002 (2)
C20.019 (2)0.022 (2)0.033 (3)0.006 (2)0.002 (2)0.010 (2)
C30.027 (2)0.017 (2)0.030 (2)0.001 (2)0.002 (2)0.003 (2)
C40.020 (2)0.024 (2)0.031 (2)0.003 (2)0.005 (2)0.004 (2)
C50.014 (2)0.018 (2)0.017 (2)0.004 (2)0.000 (2)0.000 (2)
C60.014 (2)0.023 (2)0.020 (2)0.004 (2)0.001 (1)0.002 (2)
C70.025 (2)0.026 (2)0.018 (2)0.007 (2)0.001 (2)0.000 (2)
C80.031 (2)0.032 (3)0.018 (2)0.006 (2)0.004 (2)0.006 (2)
C90.032 (2)0.020 (2)0.023 (2)0.004 (2)0.009 (2)0.004 (2)
C100.025 (2)0.021 (2)0.025 (2)0.001 (2)0.004 (2)0.005 (2)
C110.018 (2)0.012 (2)0.034 (2)0.002 (2)0.005 (2)0.005 (2)
C120.017 (2)0.018 (2)0.017 (2)0.002 (2)0.001 (2)0.004 (1)
C130.018 (2)0.019 (2)0.016 (2)0.003 (2)0.001 (2)0.001 (1)
C140.016 (2)0.019 (2)0.022 (2)0.002 (2)0.002 (1)0.003 (2)
Geometric parameters (Å, º) top
Cu1—O11.958 (2)C2—C31.391 (6)
Cu1—O3i2.157 (2)C2—H20.9300
Cu1—N11.997 (3)C3—C41.370 (6)
Cu1—N21.981 (3)C3—H30.9300
Cu1—N42.015 (3)C4—C51.396 (5)
O1—C111.264 (4)C4—H40.9302
O2—C111.245 (4)C6—C71.402 (5)
O3—Cu1ii2.157 (2)C7—C81.366 (6)
O3—C141.271 (4)C7—H50.9300
O4—C141.247 (4)C8—C91.390 (5)
O5—H150.8220C8—H60.9300
O5—H160.8365C9—C101.377 (5)
N1—C11.354 (5)C9—H70.9301
N1—C51.340 (5)C10—H80.9300
N2—C61.335 (5)C11—O11.264 (4)
N2—C101.357 (5)C11—O21.245 (4)
N3—C51.378 (5)C11—C121.530 (5)
N3—C61.394 (5)C12—C111.530 (5)
N3—H90.8599C12—C131.535 (5)
N4—C121.482 (4)C12—H120.9800
N4—H100.9001C13—C141.522 (5)
N4—H110.9000C13—H130.9700
C1—C21.363 (5)C13—H140.9700
C1—H10.9300H16—O50.8365
O1—Cu1—O3i94.9 (1)C4—C3—C2119.3 (4)
O1—Cu1—N1162.7 (1)C4—C3—H3120.3422
O1—Cu1—N287.8 (1)H3—C3—C2120.3249
O1—Cu1—N483.5 (1)C5—C4—C3119.3 (4)
O3i—Cu1—N1102.4 (1)C5—C4—H4120.3693
O3i—Cu1—N2104.5 (1)H4—C4—C3120.3705
O3i—Cu1—N491.3 (1)C7—C6—N2122.5 (3)
N1—Cu1—N289.5 (1)C7—C6—N3118.0 (3)
N1—Cu1—N494.3 (1)C8—C7—C6118.3 (3)
N2—Cu1—N4162.6 (1)C8—C7—H5120.8306
C11—O1—Cu1116.6 (2)H5—C7—C6120.8366
Cu1ii—O3—C14126.1 (2)C9—C8—C7120.3 (4)
H15—O5—H16103.7063C9—C8—H6119.8735
C1—N1—Cu1118.8 (2)H6—C8—C7119.8668
C1—N1—C5117.8 (3)C10—C9—C8117.9 (4)
C5—N1—Cu1123.2 (2)C10—C9—H7121.0512
C6—N2—Cu1122.9 (2)H7—C9—C8121.0527
C6—N2—C10117.8 (3)H8—C10—N2118.4655
C10—N2—Cu1117.4 (2)H8—C10—C9118.4670
C5—N3—C6129.2 (3)O1—C11—C12117.7 (3)
C5—N3—H9115.4117O1—C11—O2124.7 (3)
C6—N3—H9115.4095O2—C11—C12117.5 (3)
C12—N4—Cu1110.2 (2)C11—C12—N4109.5 (3)
C12—N4—H10109.6151C11—C12—H12107.8129
C12—N4—H11109.6255C11—C12—C13111.1 (3)
H10—N4—Cu1109.6205C13—C12—N4112.5 (3)
H10—N4—H11108.1428C13—C12—H12107.8132
H11—N4—Cu1109.6256H12—C12—N4107.8176
C2—C1—N1123.5 (4)C14—C13—C12113.3 (3)
C2—C1—H1118.2291C14—C13—H13108.8942
H1—C1—N1118.2395C14—C13—H14108.9045
C3—C2—C1118.2 (4)H13—C13—C12108.9037
C3—C2—H2120.8867H13—C13—H14107.7389
H2—C2—C1120.8839H14—C13—C12108.9029
N1—Cu1—O1—C1187.8 (4)N1—C1—C2—C31.9 (6)
O1—Cu1—N1—C1124.4 (3)C1—C2—C3—C40.0 (5)
O1—Cu1—N2—C6126.6 (3)C2—C3—C4—C50.8 (5)
O1—Cu1—N4—C1211.8 (2)C3—C4—C5—N10.2 (4)
Cu1—O1—C11—O2178.5 (3)C3—C4—C5—N3179.9 (2)
Cu1—N1—C1—C2172.1 (3)N2—C6—C7—C81.1 (5)
Cu1—N1—C5—N37.1 (4)C6—C7—C8—C91.3 (5)
Cu1—N1—C5—C4172.7 (3)C7—C8—C9—C102.1 (6)
Cu1—N2—C6—N318.2 (4)C8—C9—C10—N20.5 (6)
Cu1—N2—C10—C9163.3 (3)O1—C11—C12—N414.4 (4)
C6—N3—C5—N128.1 (5)O2—C11—C12—N4168.6 (3)
C6—N3—C5—C4152.1 (3)N4—C12—C13—C1465.7 (4)
C5—N3—C6—N222.1 (5)C12—C13—C14—O3147.9 (3)
Cu1—N4—C12—C1116.4 (3)C12—C13—C14—O434.3 (5)
Symmetry codes: (i) x+1, y, z; (ii) x1, y, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H9···O4iii0.861.972.763 (4)153
N4—H10···O50.902.153.031 (4)166
N4—H11···O40.902.192.793 (4)124
O5—H15···O3iv0.822.082.867 (3)160
O5—H16···O2iv0.841.922.756 (4)173
Symmetry codes: (iii) x+1/2, y+1/2, z+1; (iv) x, y+1/2, z+3/2.

Experimental details

Crystal data
Chemical formula[Cu(C4H5O4N)(C10H9N3)]·H2O
Mr383.86
Crystal system, space groupOrthorhombic, P212121
Temperature (K)123
a, b, c (Å)7.018 (5), 10.364 (8), 20.72 (2)
V3)1507 (2)
Z4
Radiation typeMo Kα
µ (mm1)1.48
Crystal size (mm)0.40 × 0.04 × 0.04
Data collection
DiffractometerRigaku R-AXIS RAPID
Absorption correctionMulti-scan
(ABSCOR; Higashi, 1995)
Tmin, Tmax0.931, 0.942
No. of measured, independent and
observed [F2 > 2.0σ(F2)] reflections
13783, 3469, 2022
Rint0.061
(sin θ/λ)max1)0.649
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.040, 0.079, 0.94
No. of reflections3469
No. of parameters224
No. of restraints?
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.85, 0.90
Absolute structureFlack (1983), 1416 Friedel pairs
Absolute structure parameter0.02 (2)

Computer programs: RAPID-AUTO (Rigaku, 1998), CrystalStructure (Rigaku/MSC, 2005) and CRYSTALS (Betteridge et al., 2003), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2003), CrystalStructure (Rigaku/MSC, 2005).

Selected bond lengths (Å) top
Cu1—O11.958 (2)Cu1—N21.981 (3)
Cu1—O3i2.157 (2)Cu1—N42.015 (3)
Cu1—N11.997 (3)
Symmetry code: (i) x+1, y, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H9···O4ii0.861.972.763 (4)153
N4—H10···O50.902.153.031 (4)166
N4—H11···O40.902.192.793 (4)124
O5—H15···O3iii0.822.082.867 (3)160
O5—H16···O2iii0.841.922.756 (4)173
Symmetry codes: (ii) x+1/2, y+1/2, z+1; (iii) x, y+1/2, z+3/2.
 

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