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Acta Cryst. (2007). E63, m1865    [ doi:10.1107/S1600536807027663 ]

catena-Poly[[[(4,7-dimethyl-1,10-phenanthroline-[kappa]2N,N')copper(II)]-[mu]-terephthalato-[kappa]2O:O'] terephthalic acid hemisolvate\]

Y.-H. Wen and S. W. Ng

Abstract top

In the title compound, [Cu(C8H4O4)(C14H12N2)]n·0.5nC8H6O4, the terephthalate dianion links adjacent Cu atoms into a zigzag chain. The kink at the metal linkage is nearly a right angle. The metal atom shows square-planar coordination. The solvent terephthalic acid molecule is disordered about a centre of inversion; it occupies the space between chains but is not hydrogen bonded to any.

Comment top

Copper terephthalate forms adducts with 1,10-phenanthroline; the 1:1 adduct has been isolated as an anhydrous (Sun et al., 2001; Marsh, 2004) as well as a monoaqua (Rogan et al., 2004) compound in which the dicarboxylate dianion functions as a bridging entity. A 1:2 adduct is known having two monodeprotonated carboxylate groups (Li et al., 2006). Copper(II) terephthalate–dimethylphenanthroline crystallizes as a 1:0.5 cocrystal, (C14H14N2)(C8H4O4)Cu.0.5C8H6O4, the terephthalate dianion links adjacent copper atoms into a zigzag chain, the kink at the metal linkage being nearly a right angle. The metal atom shows square-planar coordination; if the long double-bonded oxygen atoms that are more than 2.5 Å away are considered, then the geometry is an octahedron. The lattice terephthalic acid molecule is disordered about a center-of-inversion; it occupies the space between chains but is not hydrogen bonded to any.

Related literature top

For copper terephthalate adducts with 1,10-phenanthroline, see: Sun et al. (2001); Marsh (2004); Rogan et al. (2004). For a discussion on the distortion of square-planar geometries of copper carboxylates, see: Li et al. (2005). For related literature, see: Bailey & Brown (1967); Li et al. (2006).

Experimental top

A mixture of copper(II) hydoxide carbonate (0.203 g, 1 mmol)), terephthalic acid (0.164 g, 1 mmo1) and 4,7-dimethyl-1,10-phenanthroline (0.062 g, 0.3 mmol) and water (16 ml) was placed in a 25-ml, Teflon-lined, stainless steel Parr bomb. The bomb was heated to 453 K for 72 h. It was cooled to room temperature over 72 h to furnish several blue prismatic crystals.

Refinement top

The structure when refined with only the atoms comprising the (C14H14N2)(C8H4O4)Cu portion of the asymmetric refined to a satisfactory R-index but with two voids of 382 Å3, each about a center-of-inversion. As the terephthalic acid itself is a centrosymmetric molecule displaying a volume of 174.8 Å3 (Bailey & Brown, 1967), the voids of the unit cell should accommodate four terephthalic acid molecules.

The electron densities in the difference Fourier map were allowed to refine off the symmetry element, as a half-occupancy C8H6O4 molecule. The aromatic ring was refined as a rigid hexagon of 1.39 Å sides; the C–C distances were restrained to 1.50±0.01 Å and the C–O distances to 1.25±0.01 Å. The two –C—C(=O)–OH units were restrained to be nearly flat, and other distances restraints were use to ensure sensible bond angles. The temperature factors of all C– and O-atoms were restrained to equal each other. The atoms were refined isotropically.

The H-atoms were placed in calculated positions (O–H 0.82 Å and C–H 0.93 Å), and were included in the refinement in the riding model approximation, with U(H) set to 1.2Ueq(C,O).

The final difference Fourier map had a large peak near the disordered terephthalic acid molecule.

Computing details top

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear; data reduction: CrystaClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2007).

Figures top
[Figure 1] Fig. 1. Thermal ellipsoid plot of the polymeric (C14H14N2)(C8H4O4)Cu chain; displacement ellipsoids are drawn at the 50% probability level, and H atoms as spheres of arbitrary radius. The hemiterephthalic acid molecule is not shown.
catena-Poly[[[(4,7-dimethyl-1,10-phenanthroline-\ κ2N,N')copper(II)]-µ-terephthalato-κ2O:O'] terephthalic acid hemisolvate] top
Crystal data top
[Cu(C8H4O4)(C14H12N2)]·0.5C8H6O4F(000) = 2128
Mr = 518.97Dx = 1.585 Mg m−3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 5331 reflections
a = 18.764 (5) Åθ = 2.7–27.5°
b = 17.769 (5) ŵ = 1.05 mm−1
c = 14.749 (5) ÅT = 295 K
β = 117.841 (5)°Prism, blue
V = 4348 (2) Å30.33 × 0.20 × 0.08 mm
Z = 8
Data collection top
Rigaku Mercury CCD
diffractometer		4914 independent reflections
Radiation source: fine-focus sealed tube4295 reflections with I > 2σ(I)
graphiteRint = 0.030
ω scansθmax = 27.5°, θmin = 2.3°
Absorption correction: multi-scan
(CrystalStructure; Rigaku, 2000)		h = −20→24
Tmin = 0.828, Tmax = 0.921k = −23→23
16066 measured reflectionsl = −19→19
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.066H-atom parameters constrained
wR(F2) = 0.225 w = 1/[σ2(Fo2) + (0.1414P)2 + 6.3201P]
where P = (Fo2 + 2Fc2)/3
S = 1.15(Δ/σ)max = 0.001
4914 reflectionsΔρmax = 1.41 e Å−3
290 parametersΔρmin = −0.88 e Å−3
16 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.017 (2)
Crystal data top
[Cu(C8H4O4)(C14H12N2)]·0.5C8H6O4V = 4348 (2) Å3
Mr = 518.97Z = 8
Monoclinic, C2/cMo Kα radiation
a = 18.764 (5) ŵ = 1.05 mm−1
b = 17.769 (5) ÅT = 295 K
c = 14.749 (5) Å0.33 × 0.20 × 0.08 mm
β = 117.841 (5)°
Data collection top
Rigaku Mercury CCD
diffractometer		4914 independent reflections
Absorption correction: multi-scan
(CrystalStructure; Rigaku, 2000)		4295 reflections with I > 2σ(I)
Tmin = 0.828, Tmax = 0.921Rint = 0.030
16066 measured reflectionsθmax = 27.5°
Refinement top
R[F2 > 2σ(F2)] = 0.066H-atom parameters constrained
wR(F2) = 0.225Δρmax = 1.41 e Å−3
S = 1.15Δρmin = −0.88 e Å−3
4914 reflectionsAbsolute structure: ?
290 parametersFlack parameter: ?
16 restraintsRogers parameter: ?
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
Cu10.25030 (3)0.53888 (2)0.62123 (3)0.0363 (3)
O10.30675 (15)0.50921 (15)0.76751 (19)0.0415 (6)
O20.39382 (18)0.57136 (17)0.7350 (2)0.0514 (7)
O30.28153 (19)0.44917 (15)0.5707 (2)0.0483 (7)
O40.1733 (2)0.41283 (19)0.5821 (3)0.0599 (8)
N10.20944 (18)0.59243 (18)0.4862 (2)0.0375 (6)
N20.19708 (19)0.62594 (16)0.6513 (2)0.0377 (6)
C10.3768 (2)0.53507 (18)0.7936 (3)0.0376 (8)
C20.4409 (2)0.51817 (18)0.9015 (3)0.0339 (7)
C30.4211 (2)0.5079 (2)0.9807 (3)0.0395 (7)
H30.36790.51390.96770.047*
C40.4796 (2)0.4888 (2)1.0790 (3)0.0396 (8)
H40.46560.48081.13100.048*
C50.2296 (3)0.3998 (2)0.5624 (3)0.0429 (8)
C60.2401 (2)0.3225 (2)0.5288 (3)0.0400 (8)
C70.3078 (3)0.3049 (2)0.5186 (3)0.0433 (8)
H70.34660.34160.53050.052*
C80.3184 (3)0.2329 (2)0.4908 (3)0.0440 (8)
H80.36450.22130.48510.053*
C90.2153 (2)0.5730 (2)0.4036 (3)0.0455 (9)
H90.23740.52640.40240.055*
C100.1896 (3)0.6197 (3)0.3179 (3)0.0512 (10)
H100.19560.60400.26170.061*
C110.1557 (2)0.6885 (2)0.3155 (3)0.0471 (9)
C120.1270 (4)0.7387 (4)0.2239 (4)0.0724 (15)
H12A0.14540.71950.17760.109*
H12B0.14800.78850.24530.109*
H12C0.06920.74030.18990.109*
C130.1481 (2)0.7105 (2)0.4034 (3)0.0402 (8)
C140.1757 (2)0.6606 (2)0.4854 (3)0.0364 (7)
C150.1137 (3)0.7799 (2)0.4124 (3)0.0511 (10)
H150.09660.81470.35930.061*
C160.1053 (3)0.7962 (2)0.4971 (3)0.0529 (10)
H160.08180.84160.50000.063*
C170.1317 (2)0.7453 (2)0.5817 (3)0.0409 (8)
C180.1680 (2)0.67809 (19)0.5755 (3)0.0346 (7)
C190.1238 (3)0.7575 (2)0.6720 (3)0.0499 (10)
C200.0834 (4)0.8272 (3)0.6848 (5)0.0779 (17)
H20A0.06650.81840.73610.117*
H20B0.03730.83920.62080.117*
H20C0.12070.86850.70560.117*
C210.1524 (3)0.7029 (2)0.7462 (3)0.0511 (10)
H210.14720.70920.80540.061*
C220.1889 (3)0.6385 (2)0.7348 (3)0.0465 (9)
H220.20830.60290.78710.056*
O5−0.014 (2)0.4403 (15)0.4138 (17)0.247 (5)*0.50
H5O−0.01520.43710.47580.297*0.50
O60.002 (3)0.5681 (15)0.422 (2)0.247 (5)*0.50
O70.0155 (19)0.5688 (17)−0.0359 (17)0.247 (5)*0.50
H7O0.01770.5738−0.09730.297*0.50
O8−0.005 (3)0.4375 (16)−0.0488 (18)0.247 (5)*0.50
C23−0.004 (3)0.5035 (12)0.2799 (17)0.247 (5)*0.50
C240.004 (3)0.4358 (12)0.2378 (19)0.247 (5)*0.50
H240.00720.39080.27150.297*0.50
C250.007 (2)0.4356 (12)0.1453 (17)0.247 (5)*0.50
H250.01190.39040.11710.297*0.50
C260.002 (2)0.5030 (12)0.0949 (16)0.247 (5)*0.50
C27−0.005 (2)0.5706 (12)0.1371 (18)0.247 (5)*0.50
H27−0.00860.61570.10340.297*0.50
C28−0.008 (2)0.5708 (11)0.2296 (18)0.247 (5)*0.50
H28−0.01330.61610.25780.297*0.50
C29−0.0052 (14)0.5040 (13)0.3804 (12)0.247 (5)*0.50
C300.0043 (13)0.5031 (15)−0.0064 (11)0.247 (5)*0.50
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cu10.0400 (4)0.0313 (3)0.0304 (3)0.00531 (15)0.0103 (2)−0.00028 (14)
O10.0386 (13)0.0412 (13)0.0331 (12)0.0006 (11)0.0070 (10)0.0026 (11)
O20.0572 (17)0.0521 (16)0.0401 (15)0.0015 (13)0.0189 (13)0.0137 (13)
O30.0618 (18)0.0342 (13)0.0503 (16)0.0024 (12)0.0274 (14)−0.0036 (11)
O40.0640 (19)0.0554 (18)0.066 (2)0.0006 (15)0.0347 (17)−0.0190 (15)
N10.0362 (15)0.0403 (15)0.0307 (14)0.0066 (12)0.0113 (12)−0.0007 (12)
N20.0447 (16)0.0335 (14)0.0296 (14)0.0056 (12)0.0130 (12)−0.0009 (11)
C10.044 (2)0.0295 (16)0.0325 (17)0.0036 (13)0.0121 (15)0.0007 (12)
C20.0324 (16)0.0280 (14)0.0324 (16)−0.0005 (12)0.0077 (13)0.0009 (12)
C30.0345 (17)0.0430 (18)0.0371 (17)−0.0027 (14)0.0135 (14)0.0006 (15)
C40.0405 (18)0.0426 (19)0.0364 (17)−0.0049 (15)0.0186 (15)0.0020 (14)
C50.056 (2)0.0376 (18)0.0327 (17)0.0049 (16)0.0190 (16)−0.0020 (14)
C60.058 (2)0.0342 (16)0.0301 (16)0.0034 (15)0.0224 (16)−0.0017 (13)
C70.057 (2)0.0391 (18)0.0369 (18)−0.0057 (16)0.0250 (17)−0.0035 (14)
C80.060 (2)0.0399 (18)0.0401 (19)0.0023 (16)0.0306 (18)−0.0016 (15)
C90.0422 (19)0.051 (2)0.0390 (19)0.0100 (16)0.0154 (16)−0.0019 (16)
C100.052 (2)0.068 (3)0.0363 (19)0.005 (2)0.0221 (17)−0.0003 (18)
C110.046 (2)0.055 (2)0.0383 (19)−0.0021 (17)0.0181 (16)0.0041 (17)
C120.099 (4)0.078 (3)0.044 (2)0.012 (3)0.037 (3)0.018 (2)
C130.0395 (18)0.0429 (18)0.0334 (17)−0.0022 (15)0.0129 (14)0.0026 (14)
C140.0354 (17)0.0362 (17)0.0337 (16)−0.0010 (13)0.0130 (14)−0.0020 (13)
C150.063 (3)0.042 (2)0.046 (2)0.0090 (18)0.0241 (19)0.0124 (17)
C160.067 (3)0.0343 (18)0.052 (2)0.0121 (18)0.024 (2)0.0079 (17)
C170.049 (2)0.0326 (17)0.0380 (18)0.0054 (15)0.0178 (16)−0.0004 (14)
C180.0378 (17)0.0303 (15)0.0317 (16)−0.0001 (13)0.0128 (13)−0.0007 (12)
C190.062 (2)0.0402 (19)0.046 (2)0.0099 (18)0.0236 (19)−0.0043 (16)
C200.118 (5)0.052 (3)0.071 (3)0.033 (3)0.051 (3)0.001 (2)
C210.068 (3)0.050 (2)0.0363 (19)0.005 (2)0.0253 (19)−0.0044 (17)
C220.062 (2)0.0432 (19)0.0322 (17)0.0102 (18)0.0198 (17)0.0034 (15)
Geometric parameters (Å, °) top
Cu1—O11.980 (3)C12—H12C0.9600
Cu1—O22.486 (3)C13—C141.391 (5)
Cu1—O31.961 (3)C13—C151.427 (6)
Cu1—O42.580 (4)C14—C181.435 (5)
Cu1—N12.009 (3)C15—C161.360 (6)
Cu1—N22.000 (3)C15—H150.9300
Cu1—C12.543 (4)C16—C171.430 (5)
O1—C11.271 (5)C16—H160.9300
O2—C11.234 (5)C17—C181.398 (5)
O3—C51.274 (5)C17—C191.425 (6)
O4—C51.241 (5)C19—C211.371 (6)
N1—C91.319 (5)C19—C201.510 (6)
N1—C141.365 (5)C20—H20A0.9600
N2—C221.330 (5)C20—H20B0.9600
N2—C181.355 (4)C20—H20C0.9600
C1—C21.510 (5)C21—C221.383 (6)
C2—C4i1.386 (5)C21—H210.9300
C2—C31.395 (5)C22—H220.9300
C3—C41.391 (5)O5—C291.275 (10)
C3—H30.9300O5—H5O0.9300
C4—C2i1.386 (5)O6—C291.273 (10)
C4—H40.9300O7—C301.297 (10)
C5—C61.504 (5)O7—H7O0.9300
C6—C71.383 (6)O8—C301.295 (10)
C6—C8ii1.401 (6)C23—C241.3900
C7—C81.386 (5)C23—C281.3900
C7—H70.9300C23—C291.496 (6)
C8—C6ii1.401 (6)C24—C251.3900
C8—H80.9300C24—H240.9300
C9—C101.396 (6)C25—C261.3900
C9—H90.9300C25—H250.9300
C10—C111.371 (6)C26—C271.3900
C10—H100.9300C26—C301.514 (6)
C11—C131.422 (5)C27—C281.3900
C11—C121.493 (6)C27—H270.9300
C12—H12A0.9600C28—H280.9300
C12—H12B0.9600
O1—Cu1—O395.4 (1)C14—C13—C11117.6 (4)
O1—Cu1—N1165.7 (1)C14—C13—C15118.0 (3)
O1—Cu1—N291.9 (1)C11—C13—C15124.4 (4)
O3—Cu1—N193.0 (1)N1—C14—C13123.7 (3)
O3—Cu1—N2168.9 (1)N1—C14—C18115.6 (3)
N1—Cu1—N281.6 (1)C13—C14—C18120.7 (3)
O3—Cu1—C193.05 (12)C16—C15—C13121.4 (4)
O1—Cu1—C129.41 (11)C16—C15—H15119.3
N2—Cu1—C197.39 (12)C13—C15—H15119.3
N1—Cu1—C1138.58 (12)C15—C16—C17121.7 (4)
C1—O1—Cu1100.7 (2)C15—C16—H16119.2
C5—O3—Cu1104.2 (2)C17—C16—H16119.2
C9—N1—C14117.6 (3)C18—C17—C19117.2 (3)
C9—N1—Cu1129.3 (3)C18—C17—C16117.7 (4)
C14—N1—Cu1112.9 (2)C19—C17—C16125.1 (3)
C22—N2—C18118.2 (3)N2—C18—C17123.5 (3)
C22—N2—Cu1128.4 (3)N2—C18—C14116.0 (3)
C18—N2—Cu1113.4 (2)C17—C18—C14120.5 (3)
O2—C1—O1123.1 (3)C21—C19—C17117.7 (4)
O2—C1—C2120.2 (4)C21—C19—C20120.9 (4)
O1—C1—C2116.7 (3)C17—C19—C20121.3 (4)
O2—C1—Cu173.2 (2)C19—C20—H20A109.5
O1—C1—Cu149.90 (17)C19—C20—H20B109.5
C2—C1—Cu1166.2 (3)H20A—C20—H20B109.5
C4i—C2—C3119.8 (3)C19—C20—H20C109.5
C4i—C2—C1119.1 (3)H20A—C20—H20C109.5
C3—C2—C1121.0 (3)H20B—C20—H20C109.5
C4—C3—C2121.0 (3)C19—C21—C22121.4 (4)
C4—C3—H3119.5C19—C21—H21119.3
C2—C3—H3119.5C22—C21—H21119.3
C2i—C4—C3119.2 (3)N2—C22—C21121.9 (4)
C2i—C4—H4120.4N2—C22—H22119.0
C3—C4—H4120.4C21—C22—H22119.0
O4—C5—O3123.1 (4)C29—O5—H5O120.0
O4—C5—C6120.3 (4)C30—O7—H7O120.0
O3—C5—C6116.6 (3)C24—C23—C28120.0
C7—C6—C8ii119.3 (3)C24—C23—C29120.2 (6)
C7—C6—C5120.8 (4)C28—C23—C29119.8 (6)
C8ii—C6—C5119.9 (3)C23—C24—C25120.0
C6—C7—C8120.5 (4)C23—C24—H24120.0
C6—C7—H7119.8C25—C24—H24120.0
C8—C7—H7119.8C24—C25—C26120.0
C7—C8—C6ii120.2 (4)C24—C25—H25120.0
C7—C8—H8119.9C26—C25—H25120.0
C6ii—C8—H8119.9C25—C26—C27120.0
N1—C9—C10122.5 (4)C25—C26—C30120.3 (6)
N1—C9—H9118.8C27—C26—C30119.7 (6)
C10—C9—H9118.8C28—C27—C26120.0
C11—C10—C9120.9 (4)C28—C27—H27120.0
C11—C10—H10119.6C26—C27—H27120.0
C9—C10—H10119.6C27—C28—C23120.0
C10—C11—C13117.7 (4)C27—C28—H28120.0
C10—C11—C12121.5 (4)C23—C28—H28120.0
C13—C11—C12120.8 (4)O6—C29—O5127.6 (10)
C11—C12—H12A109.5O6—C29—C23116.2 (9)
C11—C12—H12B109.5O5—C29—C23116.1 (9)
H12A—C12—H12B109.5O8—C30—O7131.0 (10)
C11—C12—H12C109.5O8—C30—C26114.4 (9)
H12A—C12—H12C109.5O7—C30—C26114.6 (9)
H12B—C12—H12C109.5
O3—Cu1—O1—C186.5 (2)C9—C10—C11—C12−179.2 (5)
N2—Cu1—O1—C1−101.8 (2)C10—C11—C13—C140.0 (5)
N1—Cu1—O1—C1−39.1 (6)C12—C11—C13—C14179.5 (4)
O1—Cu1—O3—C583.7 (3)C10—C11—C13—C15−179.5 (4)
N2—Cu1—O3—C5−47.5 (7)C12—C11—C13—C150.0 (7)
N1—Cu1—O3—C5−107.9 (3)C9—N1—C14—C13−0.7 (5)
C1—Cu1—O3—C5113.1 (3)Cu1—N1—C14—C13175.4 (3)
O3—Cu1—N1—C9−8.1 (4)C9—N1—C14—C18177.9 (3)
O1—Cu1—N1—C9117.8 (5)Cu1—N1—C14—C18−6.0 (4)
N2—Cu1—N1—C9−178.4 (4)C11—C13—C14—N10.2 (5)
C1—Cu1—N1—C989.9 (4)C15—C13—C14—N1179.7 (4)
O3—Cu1—N1—C14176.4 (2)C11—C13—C14—C18−178.3 (3)
O1—Cu1—N1—C14−57.7 (6)C15—C13—C14—C181.2 (5)
N2—Cu1—N1—C146.1 (2)C14—C13—C15—C16−2.1 (6)
C1—Cu1—N1—C14−85.6 (3)C11—C13—C15—C16177.4 (4)
O3—Cu1—N2—C22114.9 (7)C13—C15—C16—C171.0 (7)
O1—Cu1—N2—C22−16.6 (4)C15—C16—C17—C181.0 (7)
N1—Cu1—N2—C22176.2 (4)C15—C16—C17—C19−178.7 (4)
C1—Cu1—N2—C22−45.6 (4)C22—N2—C18—C171.8 (5)
O3—Cu1—N2—C18−66.5 (7)Cu1—N2—C18—C17−176.9 (3)
O1—Cu1—N2—C18162.0 (3)C22—N2—C18—C14−177.8 (3)
N1—Cu1—N2—C18−5.2 (2)Cu1—N2—C18—C143.5 (4)
C1—Cu1—N2—C18133.0 (3)C19—C17—C18—N2−1.7 (6)
Cu1—O1—C1—O23.3 (4)C16—C17—C18—N2178.5 (4)
Cu1—O1—C1—C2−175.6 (2)C19—C17—C18—C14177.9 (4)
O3—Cu1—C1—O287.2 (2)C16—C17—C18—C14−1.9 (6)
O1—Cu1—C1—O2−177.1 (3)N1—C14—C18—N21.8 (5)
N2—Cu1—C1—O2−96.5 (2)C13—C14—C18—N2−179.6 (3)
N1—Cu1—C1—O2−10.8 (3)N1—C14—C18—C17−177.9 (3)
O3—Cu1—C1—O1−95.7 (2)C13—C14—C18—C170.8 (5)
N2—Cu1—C1—O180.6 (2)C18—C17—C19—C210.3 (6)
N1—Cu1—C1—O1166.4 (2)C16—C17—C19—C21−180.0 (4)
O3—Cu1—C1—C2−79.0 (11)C18—C17—C19—C20−178.2 (5)
O1—Cu1—C1—C216.6 (10)C16—C17—C19—C201.5 (7)
N2—Cu1—C1—C297.3 (11)C17—C19—C21—C220.9 (7)
N1—Cu1—C1—C2−177.0 (10)C20—C19—C21—C22179.4 (5)
O2—C1—C2—C4i−29.4 (5)C18—N2—C22—C21−0.5 (6)
O1—C1—C2—C4i149.5 (3)Cu1—N2—C22—C21178.0 (3)
Cu1—C1—C2—C4i135.3 (10)C19—C21—C22—N2−0.9 (7)
O2—C1—C2—C3152.0 (4)C28—C23—C24—C250.0
O1—C1—C2—C3−29.1 (5)C29—C23—C24—C25−179 (3)
Cu1—C1—C2—C3−43.3 (12)C23—C24—C25—C260.0
C4i—C2—C3—C4−1.7 (6)C24—C25—C26—C270.0
C1—C2—C3—C4176.9 (3)C24—C25—C26—C30−179 (3)
C2—C3—C4—C2i1.7 (6)C25—C26—C27—C280.0
Cu1—O3—C5—O41.4 (5)C30—C26—C27—C28179 (3)
Cu1—O3—C5—C6−177.5 (3)C26—C27—C28—C230.0
O4—C5—C6—C7−172.1 (4)C24—C23—C28—C270.0
O3—C5—C6—C76.7 (5)C29—C23—C28—C27179 (3)
O4—C5—C6—C8ii6.7 (6)C24—C23—C29—O6168 (2)
O3—C5—C6—C8ii−174.4 (3)C28—C23—C29—O6−11 (2)
C8ii—C6—C7—C8−0.9 (6)C24—C23—C29—O5−12 (2)
C5—C6—C7—C8178.0 (3)C28—C23—C29—O5169 (2)
C6—C7—C8—C6ii0.9 (6)C25—C26—C30—O813 (2)
C14—N1—C9—C101.0 (6)C27—C26—C30—O8−166 (2)
Cu1—N1—C9—C10−174.3 (3)C25—C26—C30—O7−167 (2)
N1—C9—C10—C11−0.8 (7)C27—C26—C30—O714 (2)
C9—C10—C11—C130.3 (6)
Symmetry codes: (i) −x+1, −y+1, −z+2; (ii) −x+1/2, −y+1/2, −z+1.
Table 1
Selected geometric parameters (Å, °) top
Cu1—O11.980 (3)Cu1—O42.580 (4)
Cu1—O22.486 (3)Cu1—N12.009 (3)
Cu1—O31.961 (3)Cu1—N22.000 (3)
O1—Cu1—O395.4 (1)O3—Cu1—N193.0 (1)
O1—Cu1—N1165.7 (1)O3—Cu1—N2168.9 (1)
O1—Cu1—N291.9 (1)N1—Cu1—N281.6 (1)
Acknowledgements top

We thank the Foundation of the Zhejiang Key Laboratory for Reactive Chemistry on Solid Surfaces (No. 0506) and the University of Malaya for supporting this study.

references
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