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In the title complex, [Cu(C6H6O2)(C10H9N3)(H2O)]·3H2O, the Cu atom has a distorted cis-square-pyramidal geometry formed by two O atoms of a bidentate cyclo­butane-1,1-dicarboxyl­ate anion, two N atoms of a bidentate di-2-pyridylamine (bpa) mol­ecule and a water O atom. In the crystal structure, the complex mol­ecules are connected by hydrogen bonds through the water mol­ecules, and by π–π stacking inter­actions between bpa ligands.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680700390X/tk2121sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680700390X/tk2121Isup2.hkl
Contains datablock I

CCDC reference: 636817

Key indicators

  • Single-crystal X-ray study
  • T = 123 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.021
  • wR factor = 0.060
  • Data-to-parameter ratio = 15.8

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT148_ALERT_3_B su on the a - Axis is Too Large (x 1000) . 9 Ang.
Alert level C PLAT154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000) 3000 Deg. PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.74 Ratio PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Cu1 - O3 .. 5.10 su PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Cu1 - N2 .. 5.01 su
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 4 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 3 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO; 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.

Aqua(cyclobutane-1,1-dicarboxylato-κ2O,O')(di-2-pyridylamine- κ2N,N')copper(II) trihydrate top
Crystal data top
[Cu(C6H6O2)(C10H9N3)(H2O)]·3H2OZ = 2
Mr = 448.92F(000) = 466
Triclinic, P1Dx = 1.558 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.7107 Å
a = 8.810 (9) ÅCell parameters from 9199 reflections
b = 11.19 (1) Åθ = 3.1–27.5°
c = 11.203 (9) ŵ = 1.19 mm1
α = 70.31 (3)°T = 123 K
β = 80.18 (3)°Prism, blue
γ = 67.11 (3)°0.30 × 0.30 × 0.20 mm
V = 957.0 (15) Å3
Data collection top
Rigaku R-AXIS RAPID
diffractometer
4099 reflections with F2 > 2σ(F2)
Detector resolution: 10.0 pixels mm-1Rint = 0.011
ω scansθmax = 27.5°
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)
h = 1111
Tmin = 0.712, Tmax = 0.789k = 1413
9508 measured reflectionsl = 1414
4401 independent reflections
Refinement top
Refinement on F2H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.021 w = 1/[σ2(Fo2) + (0.0317P)2 + 0.4273P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.060(Δ/σ)max < 0.001
S = 1.08Δρmax = 0.38 e Å3
4401 reflectionsΔρmin = 0.37 e Å3
278 parameters
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
Cu10.32486 (2)0.26739 (1)0.35005 (1)0.01211 (6)
O10.5404 (1)0.11967 (9)0.37828 (8)0.0155 (2)
O20.7971 (1)0.0256 (1)0.31116 (9)0.0191 (2)
O30.3294 (1)0.2433 (1)0.18422 (9)0.0185 (2)
O40.4803 (1)0.1756 (1)0.02323 (9)0.0206 (2)
O50.1651 (1)0.1409 (1)0.43572 (9)0.0172 (2)
O60.2642 (1)0.0369 (1)0.05094 (9)0.0206 (2)
O70.1225 (1)0.0033 (1)0.2911 (1)0.0198 (2)
O80.1810 (1)0.7658 (1)0.5043 (1)0.0238 (2)
N10.1480 (1)0.4507 (1)0.2973 (1)0.0147 (2)
N20.3484 (1)0.2981 (1)0.5091 (1)0.0132 (2)
N30.2311 (1)0.5375 (1)0.4301 (1)0.0171 (2)
C10.0482 (2)0.4761 (1)0.2046 (1)0.0203 (3)
C20.0570 (2)0.6034 (2)0.1454 (1)0.0247 (3)
C30.0626 (2)0.7128 (1)0.1814 (1)0.0244 (3)
C40.0330 (2)0.6893 (1)0.2770 (1)0.0209 (3)
C50.1374 (2)0.5557 (1)0.3347 (1)0.0148 (2)
C60.3154 (1)0.4211 (1)0.5209 (1)0.0137 (2)
C70.3666 (2)0.4372 (1)0.6249 (1)0.0187 (3)
C80.4461 (2)0.3240 (1)0.7196 (1)0.0209 (3)
C90.4736 (2)0.1957 (1)0.7105 (1)0.0192 (3)
C100.4257 (2)0.1871 (1)0.6047 (1)0.0161 (2)
C110.6132 (2)0.2215 (1)0.1636 (1)0.0155 (2)
C120.7604 (2)0.2301 (2)0.0683 (1)0.0260 (3)
C130.7653 (2)0.3446 (2)0.1133 (2)0.0373 (4)
C140.5892 (2)0.3643 (1)0.1732 (1)0.0229 (3)
C150.6568 (2)0.1138 (1)0.2928 (1)0.0142 (2)
C160.4651 (2)0.2121 (1)0.1193 (1)0.0152 (2)
H10.05170.40340.18020.024*
H20.12330.61660.08240.030*
H30.13060.80070.14090.029*
H40.02900.76080.30360.025*
H50.34680.52360.62930.022*
H60.48130.33250.78900.025*
H70.52360.11760.77510.023*
H80.44700.10140.59780.019*
H90.23820.61080.43370.021*
H100.85820.14840.08660.031*
H110.73320.25900.01980.031*
H120.84820.31380.17470.045*
H130.77330.42290.04450.045*
H140.50340.43900.12110.027*
H150.57640.36870.25950.027*
H160.16730.09670.39040.026*
H170.18420.09140.50700.026*
H180.32260.02890.03120.031*
H190.32060.08310.04070.031*
H200.16220.01280.21980.030*
H210.02460.02190.28520.030*
H220.08500.78810.52850.036*
H230.18610.83060.44580.036*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cu10.01284 (8)0.01218 (8)0.01185 (8)0.00338 (6)0.00055 (5)0.00554 (6)
O10.0157 (4)0.0134 (4)0.0139 (4)0.0032 (4)0.0023 (3)0.0035 (3)
O20.0133 (4)0.0220 (5)0.0197 (5)0.0041 (4)0.0003 (4)0.0064 (4)
O30.0163 (5)0.0251 (5)0.0181 (5)0.0067 (4)0.0001 (4)0.0125 (4)
O40.0228 (5)0.0267 (5)0.0152 (5)0.0076 (4)0.0005 (4)0.0119 (4)
O50.0205 (5)0.0178 (5)0.0152 (4)0.0089 (4)0.0003 (4)0.0050 (4)
O60.0192 (5)0.0218 (5)0.0195 (5)0.0043 (4)0.0024 (4)0.0073 (4)
O70.0153 (5)0.0255 (5)0.0199 (5)0.0083 (4)0.0009 (4)0.0080 (4)
O80.0225 (5)0.0162 (5)0.0321 (6)0.0060 (4)0.0030 (4)0.0096 (4)
N10.0136 (5)0.0157 (5)0.0137 (5)0.0036 (4)0.0013 (4)0.0047 (4)
N20.0135 (5)0.0125 (5)0.0124 (5)0.0032 (4)0.0012 (4)0.0038 (4)
N30.0224 (6)0.0107 (5)0.0186 (5)0.0040 (4)0.0057 (4)0.0046 (4)
C10.0158 (6)0.0265 (7)0.0195 (6)0.0055 (6)0.0021 (5)0.0097 (6)
C20.0171 (7)0.0327 (8)0.0191 (7)0.0035 (6)0.0059 (5)0.0053 (6)
C30.0185 (7)0.0218 (7)0.0211 (7)0.0002 (6)0.0040 (5)0.0012 (5)
C40.0215 (7)0.0144 (6)0.0212 (7)0.0025 (5)0.0021 (5)0.0026 (5)
C50.0144 (6)0.0144 (6)0.0133 (6)0.0043 (5)0.0002 (4)0.0027 (5)
C60.0135 (6)0.0140 (6)0.0133 (6)0.0044 (5)0.0002 (4)0.0046 (5)
C70.0222 (7)0.0193 (7)0.0178 (6)0.0076 (5)0.0019 (5)0.0088 (5)
C80.0218 (7)0.0279 (7)0.0148 (6)0.0086 (6)0.0029 (5)0.0079 (5)
C90.0177 (6)0.0202 (7)0.0138 (6)0.0030 (5)0.0029 (5)0.0014 (5)
C100.0159 (6)0.0136 (6)0.0149 (6)0.0030 (5)0.0002 (5)0.0025 (5)
C110.0169 (6)0.0184 (6)0.0126 (6)0.0092 (5)0.0014 (5)0.0041 (5)
C120.0237 (7)0.0384 (9)0.0172 (7)0.0176 (7)0.0051 (5)0.0051 (6)
C130.042 (1)0.047 (1)0.0355 (9)0.0349 (9)0.0076 (7)0.0089 (8)
C140.0334 (8)0.0196 (7)0.0205 (7)0.0165 (6)0.0023 (6)0.0032 (5)
C150.0162 (6)0.0150 (6)0.0145 (6)0.0073 (5)0.0001 (5)0.0065 (5)
C160.0183 (6)0.0140 (6)0.0131 (6)0.0056 (5)0.0014 (5)0.0036 (5)
Geometric parameters (Å, º) top
Cu1—O11.962 (2)C2—H20.9301
Cu1—O31.957 (1)C3—C41.368 (2)
Cu1—O52.254 (3)C3—H30.9300
Cu1—N11.999 (2)C4—C51.407 (2)
Cu1—N21.983 (1)C4—H40.9300
O1—C151.276 (2)C6—C71.406 (2)
O2—C151.243 (1)C7—C81.371 (2)
O3—C161.276 (2)C7—H50.9300
O4—C161.244 (2)C8—C91.396 (2)
O5—H160.8136C8—H60.9300
O5—H170.8050C9—C101.369 (2)
O6—H180.7951C9—H70.9301
O6—H190.8167C10—H80.9301
O7—H200.8048C11—C121.545 (2)
O7—H210.8137C11—C141.566 (2)
O8—H220.8091C11—C151.532 (2)
O8—H230.8073C11—C161.524 (2)
N1—C11.360 (2)C12—C131.545 (3)
N1—C51.340 (2)C12—H100.9700
N2—C61.340 (2)C12—H110.9700
N2—C101.359 (1)C13—C141.544 (3)
N3—C51.375 (2)C13—H120.9700
N3—C61.376 (1)C13—H130.9700
N3—H90.8601C14—H140.9700
C1—N11.360 (2)C14—H150.9700
C1—C21.368 (2)H1—C10.9300
C1—H10.9300H18—O60.7951
C2—C11.368 (2)H21—O70.8137
C2—C31.394 (3)
O1—Cu1—O388.28 (4)H4—C4—C3120.3843
O1—Cu1—O598.10 (4)C7—C6—N2121.8 (1)
O1—Cu1—N1162.85 (5)C7—C6—N3117.2 (1)
O1—Cu1—N287.89 (4)C8—C7—C6119.1 (2)
O3—Cu1—O591.06 (5)C8—C7—H5120.4225
O3—Cu1—N190.91 (4)H5—C7—C6120.4319
O3—Cu1—N2171.99 (5)C9—C8—C7119.1 (2)
O5—Cu1—N199.04 (4)C9—C8—H6120.4364
O5—Cu1—N296.45 (5)H6—C8—C7120.4363
N1—Cu1—N290.68 (5)C10—C9—C8118.8 (1)
C15—O1—Cu1121.73 (7)C10—C9—H7120.6231
C16—O3—Cu1120.4 (1)H7—C9—C8120.6266
H16—O5—Cu1110.8889H8—C10—N2118.5232
H16—O5—H17109.1213H8—C10—C9118.5282
H17—O5—Cu1116.1636C12—C11—C1488.8 (1)
H18—O6—H19105.8306C12—C11—C15115.7 (1)
H20—O7—H21105.8582C12—C11—C16118.5 (1)
H22—O8—H23104.3396C14—C11—C15110.1 (1)
C1—N1—Cu1118.2 (1)C14—C11—C16115.4 (1)
C1—N1—C5117.7 (1)C15—C11—C16107.4 (1)
C5—N1—Cu1123.38 (9)C13—C12—C1188.7 (1)
C6—N2—Cu1123.80 (8)C13—C12—H10113.8605
C6—N2—C10118.1 (1)C13—C12—H11113.8637
C10—N2—Cu1117.3 (1)H10—C12—C11113.8620
C5—N3—C6130.4 (1)H10—C12—H11111.0768
C5—N3—H9114.7920H11—C12—C11113.8674
C6—N3—H9114.7896C14—C13—C1289.6 (2)
N1—C1—H1118.3673C14—C13—H12113.7223
N1—C1—C2123.3 (2)C14—C13—H13113.7171
C2—C1—H1118.3670H12—C13—C12113.7217
C1—C2—C3118.7 (2)H12—C13—H13110.9605
C1—C2—H2120.6652H13—C13—C12113.7149
C3—C2—H2120.6684H14—C14—C11113.9872
C4—C3—C2119.1 (1)H14—C14—H15111.1899
C4—C3—H3120.4208H14—C14—C13113.9953
H3—C3—C2120.4308H15—C14—C11113.9871
C5—C4—H4120.3750H15—C14—C13113.9904
C5—C4—C3119.2 (2)
O3—Cu1—O1—C1545.5 (1)N1—C1—C2—C30.1 (2)
O1—Cu1—O3—C1635.9 (1)C1—C2—C3—C41.9 (2)
O1—Cu1—O5—H1671.7C2—C3—C4—C51.4 (2)
O1—Cu1—N1—C1112.3 (2)C3—C4—C5—N11.1 (2)
O1—Cu1—N2—C6134.7 (1)C3—C4—C5—N3179.9 (1)
Cu1—O1—C15—O2175.7 (1)N2—C6—C7—C83.0 (2)
Cu1—O1—C15—C115.1 (2)C6—C7—C8—C90.2 (2)
Cu1—O3—C16—O4168.8 (1)C7—C8—C9—C102.4 (2)
Cu1—O3—C16—C1111.4 (2)C8—C9—C10—N21.8 (2)
Cu1—N1—C1—C2168.2 (1)C14—C11—C12—C1316.7 (1)
Cu1—N1—C5—N311.7 (2)C12—C11—C14—C1316.8 (1)
Cu1—N1—C5—C4167.1 (1)C12—C11—C15—O1169.7 (1)
Cu1—N2—C6—N313.2 (2)C12—C11—C15—O211.1 (2)
Cu1—N2—C10—C9169.0 (1)C12—C11—C16—O3160.8 (1)
C6—N3—C5—N116.8 (2)C12—C11—C16—O419.0 (2)
C6—N3—C5—C4164.4 (1)C11—C12—C13—C1417.0 (1)
C5—N3—C6—N216.1 (2)C12—C13—C14—C1116.8 (1)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H9···O80.862.002.799 (2)154
O5—H16···O70.811.932.734 (2)168
O5—H17···O2i0.812.012.811 (3)173 (1)
O6—H18···O4ii0.792.042.818 (3)164 (2)
O6—H19···O40.822.002.810 (2)173
O7—H20···O60.811.932.734 (3)178
O7—H21···O2iii0.811.962.756 (2)164 (1)
O8—H22···O5iv0.812.052.852 (3)172 (1)
O8—H23···O7v0.812.072.848 (3)161 (2)
Symmetry codes: (i) x+1, y, z+1; (ii) x+1, y, z; (iii) x1, y, z; (iv) x, y+1, z+1; (v) x, y+1, z.
 

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