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In the title compound, [Cu2(C8H4O4)(C10H8N2)4](ClO4)2·2H2O, each Cu atom is surrounded by an O atom of a terephthalate dianion and four N atoms of two 2,2′-bi­pyridine mol­ecules, forming a distorted square-pyramidal geometry. The terephthalate dianion functions as a bridge between two Cu atoms and forms a dinuclear complex.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805001753/is6040sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805001753/is6040Isup2.hkl
Contains datablock I

CCDC reference: 263571

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.045
  • wR factor = 0.123
  • Data-to-parameter ratio = 12.2

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT430_ALERT_2_B Short Inter D...A Contact O6 .. O6 .. 2.82 Ang.
Alert level C PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.13 PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for Cl1 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 10 N3 -CU1 -N2 -C10 -168.70 1.00 1.555 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 14 N3 -CU1 -N2 -C6 11.50 1.20 1.555 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 18 N2 -CU1 -N3 -C15 -106.90 1.10 1.555 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 22 N2 -CU1 -N3 -C11 68.80 1.10 1.555 1.555 1.555 1.555
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 7 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 2 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 5 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Siemens, 1997); cell refinement: SAINT (Siemens, 1997); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-II (Johnson, 1976); software used to prepare material for publication: SHELXL97.

µ-Terephthalato-bis[bis(2,2'-bipyridine)copper(II)] diperchlorate dihydrate top
Crystal data top
[Cu(C8H4O4)(C10H8N2)4](ClO4)2·2H2OZ = 1
Mr = 1150.86F(000) = 588
Triclinic, P1Dx = 1.620 Mg m3
Hall symbol: -P1Mo Kα radiation, λ = 0.71073 Å
a = 9.9505 (14) ÅCell parameters from 4176 reflections
b = 11.1049 (14) Åθ = 1.9–25.2°
c = 12.1187 (14) ŵ = 1.09 mm1
α = 74.621 (2)°T = 298 K
β = 66.750 (2)°Pressom, blue
γ = 89.352 (2)°0.35 × 0.20 × 0.17 mm
V = 1179.7 (3) Å3
Data collection top
Bruker APEX area-detector
diffractometer
4176 independent reflections
Radiation source: fine-focus sealed tube3707 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.014
φ and ω scansθmax = 25.2°, θmin = 1.9°
Absorption correction: integration
(SADABS; Bruker, 2002)
h = 119
Tmin = 0.77, Tmax = 0.83k = 1313
6347 measured reflectionsl = 1413
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.045Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.123H atoms treated by a mixture of independent and constrained refinement
S = 1.05 w = 1/[σ2(Fo2) + (0.0732P)2 + 0.902P]
where P = (Fo2 + 2Fc2)/3
4176 reflections(Δ/σ)max < 0.001
342 parametersΔρmax = 0.86 e Å3
2 restraintsΔρmin = 0.40 e Å3
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
xyzUiso*/Ueq
Cu10.36934 (4)0.19186 (3)0.16991 (3)0.03013 (15)
N40.4615 (3)0.0483 (2)0.2763 (2)0.0355 (6)
N20.5299 (3)0.2419 (2)0.0024 (2)0.0324 (5)
N30.2136 (3)0.1565 (2)0.3450 (2)0.0320 (5)
O10.2595 (2)0.0790 (2)0.1239 (2)0.0377 (5)
N10.4694 (3)0.3450 (2)0.1805 (2)0.0344 (6)
O20.1371 (3)0.2446 (2)0.0948 (2)0.0459 (6)
C210.1627 (3)0.1360 (3)0.0908 (3)0.0345 (7)
C150.2327 (3)0.0680 (3)0.4362 (3)0.0331 (7)
C220.0778 (3)0.0650 (3)0.0444 (3)0.0319 (6)
C60.6248 (3)0.3411 (3)0.0265 (3)0.0337 (7)
C50.5913 (3)0.3981 (3)0.0775 (3)0.0330 (7)
C160.3654 (3)0.0001 (3)0.3951 (3)0.0354 (7)
C20.5144 (4)0.4903 (3)0.2781 (4)0.0488 (9)
H20.48730.51960.34830.059*
C240.0795 (3)0.0641 (3)0.0630 (3)0.0364 (7)
H240.13440.10750.10440.044*
C110.0969 (3)0.2232 (3)0.3748 (3)0.0376 (7)
H110.08360.28330.31110.045*
C230.0013 (3)0.1287 (3)0.0210 (3)0.0368 (7)
H230.00150.21530.03640.044*
C140.1348 (4)0.0454 (3)0.5597 (3)0.0440 (8)
H140.14880.01580.62230.053*
C10.4325 (4)0.3910 (3)0.2790 (3)0.0429 (8)
H10.34850.35430.35060.051*
C100.5502 (4)0.1868 (3)0.0922 (3)0.0406 (7)
H100.48640.11710.07470.049*
C70.7414 (4)0.3848 (3)0.1418 (3)0.0438 (8)
H70.80750.45180.15660.053*
C170.3880 (4)0.1069 (3)0.4736 (3)0.0474 (8)
H170.31930.14000.55560.057*
C120.0025 (4)0.2052 (3)0.4958 (3)0.0447 (8)
H120.08110.25340.51420.054*
C90.6611 (4)0.2289 (3)0.2094 (3)0.0467 (8)
H90.67000.19040.27100.056*
C40.6760 (4)0.4993 (3)0.0705 (3)0.0447 (8)
H40.75880.53590.00220.054*
C80.7594 (4)0.3288 (4)0.2344 (3)0.0488 (9)
H80.83670.35810.31280.059*
C200.5868 (4)0.0051 (3)0.2346 (4)0.0461 (8)
H200.65660.03140.15370.055*
C30.6363 (4)0.5452 (3)0.1723 (4)0.0514 (9)
H30.69220.61350.16920.062*
C130.0156 (4)0.1148 (4)0.5896 (3)0.0508 (9)
H130.05140.10040.67230.061*
C190.6156 (4)0.1111 (4)0.3067 (4)0.0522 (9)
H190.70220.14720.27440.063*
C180.5152 (5)0.1633 (4)0.4270 (4)0.0560 (10)
H180.53220.23590.47700.067*
Cl10.18401 (10)0.47199 (10)0.61048 (10)0.0549 (3)
O70.8240 (5)0.2584 (4)0.2297 (4)0.0848 (11)
O30.2719 (7)0.3810 (5)0.6214 (6)0.161 (3)
O50.2798 (6)0.5873 (5)0.5542 (6)0.143 (2)
O40.0877 (5)0.4862 (7)0.7222 (5)0.162 (2)
O60.1173 (5)0.4585 (5)0.5324 (5)0.1347 (19)
H7A0.902 (5)0.273 (5)0.177 (4)0.09 (2)*
H7B0.827 (6)0.321 (4)0.247 (5)0.08 (2)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cu10.0278 (2)0.0319 (2)0.0295 (2)0.00276 (15)0.01034 (16)0.00875 (15)
N40.0310 (13)0.0371 (14)0.0375 (15)0.0022 (11)0.0129 (11)0.0105 (12)
N20.0315 (13)0.0314 (13)0.0324 (13)0.0004 (10)0.0124 (11)0.0067 (11)
N30.0301 (13)0.0315 (13)0.0329 (13)0.0004 (10)0.0111 (11)0.0095 (11)
O10.0326 (11)0.0421 (12)0.0421 (13)0.0032 (10)0.0173 (10)0.0144 (10)
N10.0353 (13)0.0338 (14)0.0352 (14)0.0021 (11)0.0156 (11)0.0096 (11)
O20.0549 (14)0.0357 (13)0.0567 (15)0.0011 (11)0.0312 (12)0.0152 (11)
C210.0327 (16)0.0370 (17)0.0271 (15)0.0089 (13)0.0074 (13)0.0056 (13)
C150.0331 (16)0.0341 (16)0.0323 (16)0.0038 (12)0.0139 (13)0.0084 (13)
C220.0269 (14)0.0408 (17)0.0266 (15)0.0030 (12)0.0087 (12)0.0107 (13)
C60.0322 (15)0.0308 (15)0.0379 (17)0.0013 (12)0.0169 (13)0.0049 (13)
C50.0337 (16)0.0290 (15)0.0368 (17)0.0000 (12)0.0181 (13)0.0041 (13)
C160.0362 (16)0.0363 (16)0.0382 (17)0.0007 (13)0.0185 (14)0.0124 (14)
C20.059 (2)0.049 (2)0.052 (2)0.0036 (17)0.0310 (19)0.0225 (17)
C240.0351 (16)0.0393 (17)0.0393 (17)0.0030 (13)0.0202 (14)0.0107 (14)
C110.0351 (16)0.0386 (17)0.0391 (18)0.0029 (14)0.0147 (14)0.0116 (14)
C230.0403 (17)0.0313 (16)0.0408 (18)0.0011 (13)0.0176 (14)0.0114 (14)
C140.048 (2)0.048 (2)0.0320 (17)0.0010 (16)0.0138 (15)0.0084 (15)
C10.0449 (19)0.0457 (19)0.0396 (18)0.0027 (15)0.0171 (15)0.0141 (15)
C100.0404 (18)0.0405 (18)0.0426 (18)0.0038 (14)0.0150 (15)0.0175 (15)
C70.0359 (17)0.0411 (18)0.0442 (19)0.0049 (14)0.0098 (15)0.0055 (15)
C170.057 (2)0.0434 (19)0.043 (2)0.0057 (16)0.0248 (17)0.0064 (16)
C120.0375 (18)0.050 (2)0.046 (2)0.0066 (15)0.0112 (15)0.0229 (17)
C90.047 (2)0.054 (2)0.0397 (19)0.0088 (17)0.0128 (16)0.0225 (17)
C40.0470 (19)0.0381 (18)0.045 (2)0.0117 (15)0.0201 (16)0.0031 (15)
C80.0390 (18)0.056 (2)0.0364 (19)0.0041 (16)0.0026 (15)0.0094 (16)
C200.0362 (18)0.051 (2)0.050 (2)0.0067 (15)0.0148 (16)0.0161 (17)
C30.060 (2)0.0405 (19)0.062 (2)0.0083 (17)0.035 (2)0.0122 (17)
C130.048 (2)0.064 (2)0.0333 (18)0.0002 (18)0.0055 (16)0.0186 (17)
C190.043 (2)0.056 (2)0.067 (3)0.0179 (17)0.0282 (19)0.024 (2)
C180.067 (3)0.046 (2)0.067 (3)0.0167 (19)0.042 (2)0.0126 (19)
Cl10.0445 (5)0.0625 (6)0.0639 (6)0.0086 (4)0.0284 (5)0.0180 (5)
O70.073 (3)0.077 (3)0.086 (3)0.008 (2)0.014 (2)0.023 (2)
O30.258 (7)0.124 (4)0.220 (6)0.122 (4)0.185 (6)0.107 (4)
O50.120 (4)0.102 (3)0.180 (5)0.040 (3)0.043 (4)0.022 (3)
O40.079 (3)0.244 (7)0.146 (5)0.000 (4)0.000 (3)0.102 (5)
O60.141 (4)0.162 (5)0.136 (4)0.017 (3)0.109 (4)0.014 (3)
Geometric parameters (Å, º) top
Cu1—O11.990 (2)C23—C24i1.378 (4)
Cu1—N21.998 (3)C23—H230.9300
Cu1—N32.008 (3)C14—C131.386 (5)
Cu1—N12.038 (2)C14—H140.9300
Cu1—N42.203 (3)C1—H10.9300
N4—C161.338 (4)C10—C91.369 (5)
N4—C201.344 (4)C10—H100.9300
N2—C101.333 (4)C7—C81.374 (5)
N2—C61.352 (4)C7—H70.9300
N3—C151.345 (4)C17—C181.385 (5)
N3—C111.348 (4)C17—H170.9300
O1—C211.283 (4)C12—C131.373 (5)
N1—C11.340 (4)C12—H120.9300
N1—C51.344 (4)C9—C81.375 (5)
O2—C211.239 (4)C9—H90.9300
C21—C221.509 (4)C4—C31.373 (5)
C15—C141.381 (4)C4—H40.9300
C15—C161.490 (4)C8—H80.9300
C22—C231.389 (4)C20—C191.370 (5)
C22—C241.392 (4)C20—H200.9300
C6—C71.381 (5)C3—H30.9300
C6—C51.479 (4)C13—H130.9300
C5—C41.376 (4)C19—C181.369 (6)
C16—C171.390 (5)C19—H190.9300
C2—C31.364 (5)C18—H180.9300
C2—C11.374 (5)Cl1—O31.343 (4)
C2—H20.9300Cl1—O41.365 (5)
C24—C23i1.378 (4)Cl1—O61.390 (4)
C24—H240.9300Cl1—O51.437 (4)
C11—C121.368 (5)O7—H7A0.77 (4)
C11—H110.9300O7—H7B0.78 (4)
O1—Cu1—N292.12 (10)C24i—C23—H23119.9
O1—Cu1—N392.74 (9)C22—C23—H23119.9
N2—Cu1—N3174.70 (10)C15—C14—C13119.4 (3)
O1—Cu1—N1163.82 (10)C15—C14—H14120.3
N2—Cu1—N180.93 (10)C13—C14—H14120.3
N3—Cu1—N193.83 (10)N1—C1—C2122.4 (3)
O1—Cu1—N498.74 (9)N1—C1—H1118.8
N2—Cu1—N4103.22 (10)C2—C1—H1118.8
N3—Cu1—N478.10 (10)N2—C10—C9122.6 (3)
N1—Cu1—N497.07 (10)N2—C10—H10118.7
C16—N4—C20118.5 (3)C9—C10—H10118.7
C16—N4—Cu1111.7 (2)C8—C7—C6119.7 (3)
C20—N4—Cu1129.2 (2)C8—C7—H7120.1
C10—N2—C6118.8 (3)C6—C7—H7120.1
C10—N2—Cu1126.2 (2)C18—C17—C16118.5 (3)
C6—N2—Cu1115.0 (2)C18—C17—H17120.8
C15—N3—C11119.4 (3)C16—C17—H17120.8
C15—N3—Cu1118.0 (2)C11—C12—C13118.9 (3)
C11—N3—Cu1122.4 (2)C11—C12—H12120.5
C21—O1—Cu1110.96 (19)C13—C12—H12120.5
C1—N1—C5118.5 (3)C10—C9—C8119.0 (3)
C1—N1—Cu1127.5 (2)C10—C9—H9120.5
C5—N1—Cu1113.9 (2)C8—C9—H9120.5
O2—C21—O1123.5 (3)C3—C4—C5119.0 (3)
O2—C21—C22119.5 (3)C3—C4—H4120.5
O1—C21—C22117.0 (3)C5—C4—H4120.5
N3—C15—C14120.8 (3)C7—C8—C9118.9 (3)
N3—C15—C16115.8 (3)C7—C8—H8120.5
C14—C15—C16123.4 (3)C9—C8—H8120.5
C23—C22—C24118.6 (3)N4—C20—C19122.5 (3)
C23—C22—C21120.1 (3)N4—C20—H20118.8
C24—C22—C21121.3 (3)C19—C20—H20118.8
N2—C6—C7120.9 (3)C2—C3—C4119.7 (3)
N2—C6—C5115.0 (3)C2—C3—H3120.1
C7—C6—C5124.1 (3)C4—C3—H3120.1
N1—C5—C4121.7 (3)C12—C13—C14119.3 (3)
N1—C5—C6115.1 (3)C12—C13—H13120.3
C4—C5—C6123.2 (3)C14—C13—H13120.3
N4—C16—C17121.9 (3)C18—C19—C20119.1 (3)
N4—C16—C15115.4 (3)C18—C19—H19120.5
C17—C16—C15122.7 (3)C20—C19—H19120.5
C3—C2—C1118.7 (3)C19—C18—C17119.4 (3)
C3—C2—H2120.6C19—C18—H18120.3
C1—C2—H2120.6C17—C18—H18120.3
C23i—C24—C22121.1 (3)O3—Cl1—O4114.0 (4)
C23i—C24—H24119.4O3—Cl1—O6110.7 (3)
C22—C24—H24119.4O4—Cl1—O6113.6 (3)
N3—C11—C12122.1 (3)O3—Cl1—O5105.2 (4)
N3—C11—H11118.9O4—Cl1—O5103.2 (4)
C12—C11—H11118.9O6—Cl1—O5109.4 (3)
C24i—C23—C22120.3 (3)H7A—O7—H7B94 (6)
O1—Cu1—N4—C1683.6 (2)Cu1—N2—C6—C51.7 (3)
N2—Cu1—N4—C16177.9 (2)C1—N1—C5—C41.4 (5)
N3—Cu1—N4—C167.4 (2)Cu1—N1—C5—C4177.3 (2)
N1—Cu1—N4—C1699.8 (2)C1—N1—C5—C6179.5 (3)
O1—Cu1—N4—C2087.0 (3)Cu1—N1—C5—C63.6 (3)
N2—Cu1—N4—C207.3 (3)N2—C6—C5—N11.3 (4)
N3—Cu1—N4—C20178.0 (3)C7—C6—C5—N1177.4 (3)
N1—Cu1—N4—C2089.6 (3)N2—C6—C5—C4179.6 (3)
O1—Cu1—N2—C1012.1 (3)C7—C6—C5—C41.7 (5)
N3—Cu1—N2—C10168.7 (10)C20—N4—C16—C173.6 (5)
N1—Cu1—N2—C10177.4 (3)Cu1—N4—C16—C17168.1 (3)
N4—Cu1—N2—C1087.4 (3)C20—N4—C16—C15177.1 (3)
O1—Cu1—N2—C6168.1 (2)Cu1—N4—C16—C1511.2 (3)
N3—Cu1—N2—C611.5 (12)N3—C15—C16—N410.1 (4)
N1—Cu1—N2—C62.8 (2)C14—C15—C16—N4168.7 (3)
N4—Cu1—N2—C692.4 (2)N3—C15—C16—C17169.1 (3)
O1—Cu1—N3—C1596.4 (2)C14—C15—C16—C1712.1 (5)
N2—Cu1—N3—C15106.9 (11)C23—C22—C24—C23i1.9 (5)
N1—Cu1—N3—C1598.4 (2)C21—C22—C24—C23i179.7 (3)
N4—Cu1—N3—C151.9 (2)C15—N3—C11—C121.0 (5)
O1—Cu1—N3—C1187.8 (2)Cu1—N3—C11—C12174.7 (2)
N2—Cu1—N3—C1168.8 (11)C24—C22—C23—C24i1.8 (5)
N1—Cu1—N3—C1177.4 (2)C21—C22—C23—C24i179.7 (3)
N4—Cu1—N3—C11173.8 (2)N3—C15—C14—C130.1 (5)
N2—Cu1—O1—C2194.3 (2)C16—C15—C14—C13178.8 (3)
N3—Cu1—O1—C2183.6 (2)C5—N1—C1—C20.2 (5)
N1—Cu1—O1—C2130.3 (4)Cu1—N1—C1—C2175.5 (3)
N4—Cu1—O1—C21162.0 (2)C3—C2—C1—N11.0 (5)
O1—Cu1—N1—C1115.6 (4)C6—N2—C10—C91.8 (5)
N2—Cu1—N1—C1179.0 (3)Cu1—N2—C10—C9178.3 (3)
N3—Cu1—N1—C11.8 (3)N2—C6—C7—C81.6 (5)
N4—Cu1—N1—C176.6 (3)C5—C6—C7—C8177.0 (3)
O1—Cu1—N1—C569.0 (4)N4—C16—C17—C181.1 (5)
N2—Cu1—N1—C53.5 (2)C15—C16—C17—C18179.7 (3)
N3—Cu1—N1—C5177.3 (2)N3—C11—C12—C131.2 (5)
N4—Cu1—N1—C598.8 (2)N2—C10—C9—C82.6 (5)
Cu1—O1—C21—O23.9 (4)N1—C5—C4—C31.3 (5)
Cu1—O1—C21—C22175.78 (19)C6—C5—C4—C3179.7 (3)
C11—N3—C15—C140.4 (4)C6—C7—C8—C90.9 (5)
Cu1—N3—C15—C14175.5 (2)C10—C9—C8—C71.1 (5)
C11—N3—C15—C16179.3 (3)C16—N4—C20—C194.0 (5)
Cu1—N3—C15—C163.4 (3)Cu1—N4—C20—C19166.0 (3)
O2—C21—C22—C2315.5 (4)C1—C2—C3—C41.1 (6)
O1—C21—C22—C23164.2 (3)C5—C4—C3—C20.0 (6)
O2—C21—C22—C24166.1 (3)C11—C12—C13—C140.8 (5)
O1—C21—C22—C2414.2 (4)C15—C14—C13—C120.3 (5)
C10—N2—C6—C70.3 (4)N4—C20—C19—C181.8 (6)
Cu1—N2—C6—C7179.5 (2)C20—C19—C18—C170.9 (6)
C10—N2—C6—C5178.5 (3)C16—C17—C18—C191.2 (6)
Symmetry code: (i) x, y, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O7—H7B···O4ii0.78 (4)2.48 (4)3.239 (8)164 (5)
O7—H7A···O2iii0.77 (4)2.21 (4)2.916 (5)153 (6)
Symmetry codes: (ii) x+1, y+1, z+1; (iii) x+1, y, z.
 

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