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The title complex, [Cu(C26H20NO2P2)2], contains a central CuII atom surrounded by two homoleptic bidentate ligands, which form two five-membered chelate rings. The Cu atom binds to four O atoms, resulting in a four-coordinate square-planar complex. The asymmetric unit contains half of the complex, the other half being completed by inversion symmetry. The Cu—O bond lengths have similar distances, viz. 1.9153 (10) Å for the pair opposite (trans) each other and 1.9373 (10) Å for the other (trans) pair. The P—O bond lengths are 1.5250 (11) Å, indicating significant electron delocalization across the O—P—C—P—O atoms in the chelate ring, resulting in a longer P—O bond length when compared to a formal double-bond P=O character (much shorter at approximately 1.47 Å). The two inter­secting O—Cu—O angles are both linear at 180°, whilst the remaining L-shaped O—Cu—O bond angles are 88.26 (5) and 91.74 (5)°. The C—C[triple bond]N fragment is slightly distorted from linearity at 177.44 (19)° and the C[triple bond]N bond length of 1.151 (2) Å indicates predominantly triple-bond character.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536811031564/ff2023sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536811031564/ff2023Isup2.hkl
Contains datablock I

CCDC reference: 845222

Key indicators

  • Single-crystal X-ray study
  • T = 173 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.033
  • wR factor = 0.086
  • Data-to-parameter ratio = 19.7

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT230_ALERT_2_C Hirshfeld Test Diff for C1 -- C2 .. 6.5 su PLAT910_ALERT_3_C Missing # of FCF Reflections Below Th(Min) ..... 1 PLAT912_ALERT_4_C Missing # of FCF Reflections Above STh/L= 0.600 305
Alert level G PLAT005_ALERT_5_G No _iucr_refine_instructions_details in CIF .... ? PLAT128_ALERT_4_G Alternate Setting of Space-group P21/c ....... P21/n PLAT710_ALERT_4_G Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 6 O1 -CU1 -O1 -P1 -147.00 6.00 3.556 1.555 1.555 1.555 PLAT710_ALERT_4_G Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 10 O2 -CU1 -O2 -P2 -122.00 9.00 3.556 1.555 1.555 1.555 PLAT710_ALERT_4_G Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 25 P2 -C1 -C2 -N1 18.00 0.00 1.555 1.555 1.555 1.555 PLAT710_ALERT_4_G Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 26 P1 -C1 -C2 -N1 4.00 4.00 1.555 1.555 1.555 1.555
0 ALERT level A = Most likely a serious problem - resolve or explain 0 ALERT level B = A potentially serious problem, consider carefully 3 ALERT level C = Check. Ensure it is not caused by an omission or oversight 6 ALERT level G = General information/check it is not something unexpected 0 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 1 ALERT type 3 Indicator that the structure quality may be low 6 ALERT type 4 Improvement, methodology, query or suggestion 1 ALERT type 5 Informative message, check

Comment top

The chemistry of the ligand bis(diphenylphosphane)acetonitrile, (dppm-CN), was recently revived when a facile preparation thereof was reported, starting with readily available acetonitrile (Braun et al., 2007). Development of its chemistry followed thereafter, including the observed sharp increase in acidity by the replacement of a proton with a cyano group on the bridging carbon atom (Spannhoff et al., 2009, and references therein). In continuing our interest in dinuclear gold(I) complexes (Van Zyl, 2010), we recently reported the first structural investigation of a chlorogold(I) complex with the ligand dppm-CN, (Sithole et al., 2011).

A relatively straightforward method for the preparation of complex (I) would entail the reaction between Li[NC—C(Ph2P=O)2], prepared as described (Braun et al., 2008), and CuCl2 or Cu(NO3)2 (molar ratio 2:1), leading to formation of complex (I) after removal of LiCl or LiNO3. However, in the present study, we report complex (I) was obtained in a surprisingly different manner. Formation of (I) occurred post-synthesis during the crystallization process. An initial reaction between the well characterized complexes [Au2{dppm-CN}2], and [Cu(CH3CN)4][PF6] (1:1 molar ratio) was performed in an attempt to coordinate the copper(I) center to the CN group. The Experimental section describes a complex formed and isolated from this reaction as a colorless, free-flowing powder and suggests no sign of metal oxidation (both Au(I) and Cu(I) are closed-shell d10 systems and are usually colorless or pale yellow compounds, hence any sign of oxidation leading to deep color changes for either metal is readily observed). However, during subsequent crystallization procedures obvious oxidation occurred, firstly at the metal center where the precursor colorless Cu(I) species oxidized to a green-colored Cu(II) complex. Secondly, the P atoms in the anionic [dppm-CN]¯ ligand did oxidize to the corresponding oxide analogue (not uncommon in the presence of air or moisture), and the ligand transferred also from the gold(I) center to the much more oxophillic Cu(II) center whilst retaining the negative anionic charge, i.e. it did not become protonated and thus neutral in the process. No attempt was made in this study to determine the concurrent reduced species, but presumably the Au(I) species reduced to Au(0) metal. Single crystal X-ray analysis subsequently revealed the green colored material to be identified as complex (I).

Related literature top

For recent work on bis(diphenylphosphane)acetonitrile, see: Braun et al. (2007); Spannhoff et al. (2009). For a bis(diphenylphosphane)acetonitrile complex of gold(I), see: Sithole et al. (2011) and for bis(diphenylphosphane)acetonitrile oxides and sulfides (and their lithiated structures), see: Braun et al. (2008). For background to our interest in dinuclear gold(I) complexes, see: Van Zyl (2010)

Experimental top

Preparation and characterization of complex obtained pre-crystallization: A Schlenk flask equipped with a magnetic stirrer bar was charged with previously prepared [Au2{dppm-CN}2] complex (400 mg, 0.33 mmol) dissolved in dichloromethane (5 ml). A dichloromethane (8 ml) solution of [Cu(CH3CN)4][PF6] (123 mg, 0.33 mmol) was then added dropwise to the gold-containing solution at room temperature. The solution turned cloudy and was stirred for an hour, after which all dichloromethane solvent was removed under reduced pressure. Dry Et2O (2 x 2 ml) was added to wash the product which was further dried in vacuo for 2 hrs. The product was obtained as a free flowing off-white powder. Yield: (387 mg, 0.21 mmol) 65%; Mp: 155–160 oC (decompose); 1H NMR (400 MHz, CDCl3, 298 K) δH= 7.68–7.53 (m, 40H, Ph); 31P NMR (101 MHz, CDCl3, 298 K) δP = 22.8 (s, 2P). Green single crystals were obtained by slow evaporation of a dichloromethane solution of the complex.

Refinement top

All non-hydrogen atoms are refined anisotropically. H atoms were calculated by geometrical methods and refined as a riding model, with C—H distace 0.95 Å and Uiso(H) = 1.2Ueq(C). The crystal used for the diffraction study showed no decomposition during data collection.

Structure description top

The chemistry of the ligand bis(diphenylphosphane)acetonitrile, (dppm-CN), was recently revived when a facile preparation thereof was reported, starting with readily available acetonitrile (Braun et al., 2007). Development of its chemistry followed thereafter, including the observed sharp increase in acidity by the replacement of a proton with a cyano group on the bridging carbon atom (Spannhoff et al., 2009, and references therein). In continuing our interest in dinuclear gold(I) complexes (Van Zyl, 2010), we recently reported the first structural investigation of a chlorogold(I) complex with the ligand dppm-CN, (Sithole et al., 2011).

A relatively straightforward method for the preparation of complex (I) would entail the reaction between Li[NC—C(Ph2P=O)2], prepared as described (Braun et al., 2008), and CuCl2 or Cu(NO3)2 (molar ratio 2:1), leading to formation of complex (I) after removal of LiCl or LiNO3. However, in the present study, we report complex (I) was obtained in a surprisingly different manner. Formation of (I) occurred post-synthesis during the crystallization process. An initial reaction between the well characterized complexes [Au2{dppm-CN}2], and [Cu(CH3CN)4][PF6] (1:1 molar ratio) was performed in an attempt to coordinate the copper(I) center to the CN group. The Experimental section describes a complex formed and isolated from this reaction as a colorless, free-flowing powder and suggests no sign of metal oxidation (both Au(I) and Cu(I) are closed-shell d10 systems and are usually colorless or pale yellow compounds, hence any sign of oxidation leading to deep color changes for either metal is readily observed). However, during subsequent crystallization procedures obvious oxidation occurred, firstly at the metal center where the precursor colorless Cu(I) species oxidized to a green-colored Cu(II) complex. Secondly, the P atoms in the anionic [dppm-CN]¯ ligand did oxidize to the corresponding oxide analogue (not uncommon in the presence of air or moisture), and the ligand transferred also from the gold(I) center to the much more oxophillic Cu(II) center whilst retaining the negative anionic charge, i.e. it did not become protonated and thus neutral in the process. No attempt was made in this study to determine the concurrent reduced species, but presumably the Au(I) species reduced to Au(0) metal. Single crystal X-ray analysis subsequently revealed the green colored material to be identified as complex (I).

For recent work on bis(diphenylphosphane)acetonitrile, see: Braun et al. (2007); Spannhoff et al. (2009). For a bis(diphenylphosphane)acetonitrile complex of gold(I), see: Sithole et al. (2011) and for bis(diphenylphosphane)acetonitrile oxides and sulfides (and their lithiated structures), see: Braun et al. (2008). For background to our interest in dinuclear gold(I) complexes, see: Van Zyl (2010)

Computing details top

Data collection: COSMO (Bruker, 2009); cell refinement: APEX2 (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. Molecular structure of the title complex. Ellipsoids are drawn at the 50% probability level. Unlabelled atoms are related to the reference ones by the (-x -y, 1-z) symmetry transformation.
Bis[bis(diphenylphosphinoyl)acetonitrile-κ2O,O']copper(II) top
Crystal data top
[Cu(C26H20NO2P2)2]F(000) = 974
Mr = 944.28Dx = 1.405 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 9929 reflections
a = 9.5917 (7) Åθ = 2.4–28.7°
b = 25.8793 (19) ŵ = 0.68 mm1
c = 9.6648 (7) ÅT = 173 K
β = 111.526 (1)°Block, green
V = 2231.7 (3) Å30.33 × 0.23 × 0.12 mm
Z = 2
Data collection top
Bruker APEXII CCD
diffractometer
5640 independent reflections
Radiation source: fine-focus sealed tube4832 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.036
Detector resolution: 836.6 pixels mm-1θmax = 29.1°, θmin = 2.4°
ω,and/f 0.5° scansh = 1212
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
k = 3434
Tmin = 0.807, Tmax = 0.920l = 1313
43689 measured reflections
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)] = 0.033Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.086H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0428P)2 + 1.1569P]
where P = (Fo2 + 2Fc2)/3
5640 reflections(Δ/σ)max = 0.001
286 parametersΔρmax = 0.49 e Å3
0 restraintsΔρmin = 0.32 e Å3
Crystal data top
[Cu(C26H20NO2P2)2]V = 2231.7 (3) Å3
Mr = 944.28Z = 2
Monoclinic, P21/nMo Kα radiation
a = 9.5917 (7) ŵ = 0.68 mm1
b = 25.8793 (19) ÅT = 173 K
c = 9.6648 (7) Å0.33 × 0.23 × 0.12 mm
β = 111.526 (1)°
Data collection top
Bruker APEXII CCD
diffractometer
5640 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
4832 reflections with I > 2σ(I)
Tmin = 0.807, Tmax = 0.920Rint = 0.036
43689 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0330 restraints
wR(F2) = 0.086H-atom parameters constrained
S = 1.03Δρmax = 0.49 e Å3
5640 reflectionsΔρmin = 0.32 e Å3
286 parameters
Special details top

Experimental. Data was collected using a BRUKER CCD (charge coupled device) based diffractometer equipped with an Oxford low-temperature apparatus operating at 173 K. A suitable crystal was chosen and mounted on a glass fiber or nylon loop using Paratone oil for Mo radiation and Mineral oil for Copper radiation. Data were measured using omega and phi scans of 0.5° per frame for 20 s. The total number of images were based on results from the program COSMO where redundancy was expected to be 4 and completeness to 0.83Å to 100%. Cell parameters were retrieved using APEX II software and refined using SAINT on all observed reflections.Data reduction was performed using the SAINT software which corrects for Lp. Scaling and absorption corrections were applied using SADABS6 multi-scan technique, supplied by George Sheldrick. The structures are solved by the direct method using the SHELXS97 program and refined by least squares method on F2, SHELXL97, incorporated in SHELXTL-PC V 6.14.

All H atoms were placed in calculated positions and refined using a riding model. C—H(aromatic) = 0.94 Å and Uiso(H) = 1.2Ueq(C) C—H (alaphatic) = 0.99 Å and Uiso(H) = 1.2Ueq(C) CH2 = 0.98 Å and Uiso(H) = 1.2Ueq(C) CH3 = 0.97Å and Uiso(H) = 1.5Ueq(C) N—H = 0.86 (0.92)Å and Uiso(H) = 1.2 Ueq(N) O—H(alcohol) = 0.85Åand Uiso(H) = 1.2Ueq(O) O—H(acid) = 0.82 Å and Uiso(H) = 1.5Ueq(O)

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
Cu10.00000.00000.50000.01782 (8)
P10.11652 (4)0.085542 (15)0.73438 (4)0.02022 (9)
P20.19258 (4)0.090614 (15)0.46718 (4)0.01886 (9)
O10.01591 (12)0.05965 (4)0.61444 (12)0.0222 (2)
O20.12911 (12)0.03636 (4)0.42218 (12)0.0230 (2)
N10.49225 (17)0.14605 (6)0.81575 (19)0.0374 (4)
C10.24792 (17)0.10182 (6)0.65683 (17)0.0217 (3)
C20.38298 (18)0.12620 (6)0.74163 (18)0.0243 (3)
C30.04936 (19)0.14124 (6)0.80190 (19)0.0259 (3)
C40.1033 (2)0.15090 (8)0.7557 (2)0.0349 (4)
H40.17300.12730.69110.042*
C50.1545 (3)0.19521 (8)0.8038 (3)0.0474 (5)
H50.25900.20170.77290.057*
C60.0534 (3)0.22945 (8)0.8963 (3)0.0525 (6)
H60.08840.25980.92840.063*
C70.0989 (3)0.22001 (9)0.9432 (3)0.0571 (7)
H70.16800.24381.00740.069*
C80.1504 (2)0.17605 (8)0.8966 (3)0.0442 (5)
H80.25500.16950.92910.053*
C90.19949 (18)0.04236 (6)0.88816 (18)0.0241 (3)
C100.2915 (2)0.00309 (7)0.87194 (19)0.0289 (4)
H100.32060.00280.78800.035*
C110.3408 (2)0.03571 (7)0.9783 (2)0.0336 (4)
H110.40360.06250.96700.040*
C120.2983 (2)0.03529 (8)1.1009 (2)0.0356 (4)
H120.33090.06211.17290.043*
C130.2088 (3)0.00393 (8)1.1186 (2)0.0389 (4)
H130.18120.00441.20350.047*
C140.1591 (2)0.04268 (7)1.0126 (2)0.0335 (4)
H140.09720.06961.02490.040*
C150.05405 (18)0.13679 (6)0.36258 (18)0.0248 (3)
C160.0541 (2)0.18605 (7)0.4181 (3)0.0440 (5)
H160.12790.19550.51120.053*
C170.0536 (3)0.22178 (9)0.3379 (3)0.0625 (7)
H170.05260.25580.37500.075*
C180.1616 (3)0.20742 (10)0.2045 (3)0.0596 (7)
H180.23610.23160.15050.072*
C190.1631 (2)0.15861 (10)0.1484 (2)0.0463 (5)
H190.23830.14930.05610.056*
C200.05537 (19)0.12307 (8)0.22608 (19)0.0316 (4)
H200.05570.08940.18680.038*
C210.35557 (17)0.09861 (6)0.42016 (17)0.0226 (3)
C220.3618 (2)0.13313 (7)0.3125 (2)0.0322 (4)
H220.27800.15430.26100.039*
C230.4920 (2)0.13646 (9)0.2805 (2)0.0445 (5)
H230.49680.15990.20690.053*
C240.6140 (2)0.10571 (8)0.3557 (2)0.0406 (5)
H240.70300.10850.33470.049*
C250.6072 (2)0.07084 (8)0.4614 (2)0.0344 (4)
H250.69090.04940.51180.041*
C260.47879 (18)0.06714 (7)0.49360 (19)0.0272 (3)
H260.47430.04310.56610.033*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cu10.01623 (13)0.01786 (13)0.01979 (13)0.00193 (9)0.00712 (10)0.00220 (9)
P10.02000 (19)0.02058 (19)0.02087 (19)0.00208 (14)0.00841 (15)0.00352 (14)
P20.01714 (18)0.01878 (18)0.02072 (19)0.00176 (14)0.00704 (15)0.00045 (14)
O10.0191 (5)0.0225 (5)0.0259 (6)0.0019 (4)0.0093 (4)0.0054 (4)
O20.0263 (6)0.0213 (5)0.0259 (6)0.0055 (4)0.0148 (5)0.0042 (4)
N10.0250 (8)0.0389 (9)0.0417 (9)0.0058 (6)0.0046 (7)0.0069 (7)
C10.0187 (7)0.0261 (7)0.0206 (7)0.0035 (6)0.0075 (6)0.0018 (6)
C20.0233 (8)0.0237 (7)0.0255 (8)0.0009 (6)0.0086 (6)0.0004 (6)
C30.0324 (9)0.0210 (7)0.0281 (8)0.0001 (6)0.0157 (7)0.0031 (6)
C40.0348 (10)0.0355 (10)0.0347 (10)0.0061 (8)0.0130 (8)0.0032 (8)
C50.0535 (13)0.0428 (11)0.0518 (13)0.0210 (10)0.0262 (11)0.0052 (10)
C60.0843 (18)0.0255 (9)0.0676 (15)0.0096 (10)0.0512 (14)0.0018 (10)
C70.0759 (17)0.0362 (11)0.0741 (17)0.0183 (11)0.0450 (14)0.0285 (11)
C80.0405 (11)0.0404 (11)0.0563 (13)0.0104 (9)0.0231 (10)0.0226 (10)
C90.0243 (8)0.0250 (8)0.0229 (7)0.0035 (6)0.0084 (6)0.0024 (6)
C100.0286 (9)0.0334 (9)0.0257 (8)0.0013 (7)0.0113 (7)0.0007 (7)
C110.0298 (9)0.0327 (9)0.0353 (9)0.0039 (7)0.0085 (7)0.0027 (7)
C120.0378 (10)0.0360 (9)0.0263 (9)0.0029 (8)0.0039 (7)0.0057 (7)
C130.0523 (12)0.0420 (11)0.0253 (9)0.0019 (9)0.0177 (8)0.0005 (8)
C140.0424 (10)0.0330 (9)0.0298 (9)0.0018 (8)0.0187 (8)0.0023 (7)
C150.0210 (7)0.0271 (8)0.0262 (8)0.0006 (6)0.0085 (6)0.0041 (6)
C160.0452 (11)0.0274 (9)0.0499 (12)0.0070 (8)0.0062 (10)0.0019 (8)
C170.0715 (17)0.0327 (11)0.0784 (18)0.0211 (11)0.0216 (14)0.0119 (11)
C180.0472 (13)0.0583 (15)0.0683 (16)0.0239 (11)0.0151 (12)0.0355 (13)
C190.0283 (10)0.0674 (15)0.0378 (11)0.0030 (9)0.0055 (8)0.0239 (10)
C200.0244 (8)0.0437 (10)0.0256 (8)0.0016 (7)0.0077 (7)0.0058 (7)
C210.0211 (7)0.0237 (7)0.0236 (7)0.0037 (6)0.0090 (6)0.0034 (6)
C220.0300 (9)0.0331 (9)0.0369 (10)0.0013 (7)0.0162 (8)0.0069 (7)
C230.0454 (12)0.0495 (12)0.0491 (12)0.0050 (9)0.0299 (10)0.0114 (10)
C240.0314 (10)0.0491 (11)0.0514 (12)0.0077 (8)0.0269 (9)0.0045 (9)
C250.0231 (8)0.0397 (10)0.0422 (10)0.0016 (7)0.0141 (8)0.0061 (8)
C260.0239 (8)0.0287 (8)0.0293 (8)0.0006 (6)0.0102 (7)0.0001 (7)
Geometric parameters (Å, º) top
Cu1—O21.9153 (10)C11—C121.388 (3)
Cu1—O2i1.9153 (10)C11—H110.9500
Cu1—O1i1.9373 (10)C12—C131.380 (3)
Cu1—O11.9373 (10)C12—H120.9500
P1—O11.5250 (11)C13—C141.387 (3)
P1—C11.7381 (16)C13—H130.9500
P1—C91.7953 (17)C14—H140.9500
P1—C31.7963 (16)C15—C161.383 (3)
P2—O21.5287 (11)C15—C201.397 (2)
P2—C11.7353 (16)C16—C171.391 (3)
P2—C211.7929 (16)C16—H160.9500
P2—C151.7972 (16)C17—C181.376 (4)
N1—C21.151 (2)C17—H170.9500
C1—C21.403 (2)C18—C191.373 (4)
C3—C41.388 (2)C18—H180.9500
C3—C81.392 (3)C19—C201.381 (3)
C4—C51.393 (3)C19—H190.9500
C4—H40.9500C20—H200.9500
C5—C61.374 (3)C21—C221.389 (2)
C5—H50.9500C21—C261.396 (2)
C6—C71.383 (4)C22—C231.395 (3)
C6—H60.9500C22—H220.9500
C7—C81.380 (3)C23—C241.381 (3)
C7—H70.9500C23—H230.9500
C8—H80.9500C24—C251.382 (3)
C9—C141.392 (2)C24—H240.9500
C9—C101.392 (2)C25—C261.380 (2)
C10—C111.390 (2)C25—H250.9500
C10—H100.9500C26—H260.9500
O2—Cu1—O2i180.0C12—C11—C10119.92 (17)
O2—Cu1—O1i88.26 (5)C12—C11—H11120.0
O2i—Cu1—O1i91.74 (5)C10—C11—H11120.0
O2—Cu1—O191.74 (5)C13—C12—C11120.17 (17)
O2i—Cu1—O188.26 (5)C13—C12—H12119.9
O1i—Cu1—O1180.0C11—C12—H12119.9
O1—P1—C1108.19 (7)C12—C13—C14120.08 (18)
O1—P1—C9110.39 (7)C12—C13—H13120.0
C1—P1—C9109.66 (8)C14—C13—H13120.0
O1—P1—C3108.61 (7)C13—C14—C9120.30 (18)
C1—P1—C3112.06 (8)C13—C14—H14119.9
C9—P1—C3107.93 (8)C9—C14—H14119.9
O2—P2—C1112.92 (7)C16—C15—C20119.59 (17)
O2—P2—C21109.10 (7)C16—C15—P2119.98 (14)
C1—P2—C21106.93 (7)C20—C15—P2120.42 (13)
O2—P2—C15108.40 (7)C15—C16—C17120.1 (2)
C1—P2—C15111.07 (8)C15—C16—H16119.9
C21—P2—C15108.31 (8)C17—C16—H16119.9
P1—O1—Cu1124.47 (6)C18—C17—C16119.5 (2)
P2—O2—Cu1125.94 (6)C18—C17—H17120.3
C2—C1—P2123.44 (12)C16—C17—H17120.3
C2—C1—P1121.15 (12)C19—C18—C17120.9 (2)
P2—C1—P1115.20 (9)C19—C18—H18119.5
N1—C2—C1177.44 (19)C17—C18—H18119.5
C4—C3—C8119.55 (16)C18—C19—C20120.0 (2)
C4—C3—P1120.28 (13)C18—C19—H19120.0
C8—C3—P1120.13 (14)C20—C19—H19120.0
C3—C4—C5120.01 (19)C19—C20—C15119.80 (19)
C3—C4—H4120.0C19—C20—H20120.1
C5—C4—H4120.0C15—C20—H20120.1
C6—C5—C4119.8 (2)C22—C21—C26119.65 (15)
C6—C5—H5120.1C22—C21—P2123.05 (13)
C4—C5—H5120.1C26—C21—P2117.27 (12)
C5—C6—C7120.49 (19)C21—C22—C23119.59 (17)
C5—C6—H6119.8C21—C22—H22120.2
C7—C6—H6119.8C23—C22—H22120.2
C8—C7—C6120.0 (2)C24—C23—C22120.19 (18)
C8—C7—H7120.0C24—C23—H23119.9
C6—C7—H7120.0C22—C23—H23119.9
C7—C8—C3120.1 (2)C23—C24—C25120.25 (17)
C7—C8—H8120.0C23—C24—H24119.9
C3—C8—H8120.0C25—C24—H24119.9
C14—C9—C10119.37 (16)C26—C25—C24120.03 (18)
C14—C9—P1122.14 (13)C26—C25—H25120.0
C10—C9—P1117.91 (13)C24—C25—H25120.0
C11—C10—C9120.14 (17)C25—C26—C21120.27 (17)
C11—C10—H10119.9C25—C26—H26119.9
C9—C10—H10119.9C21—C26—H26119.9
C1—P1—O1—Cu154.82 (10)C1—P1—C9—C14146.86 (15)
C9—P1—O1—Cu165.18 (10)C3—P1—C9—C1424.52 (17)
C3—P1—O1—Cu1176.68 (8)O1—P1—C9—C1077.18 (14)
O2—Cu1—O1—P159.93 (8)C1—P1—C9—C1041.93 (15)
O2i—Cu1—O1—P1120.07 (8)C3—P1—C9—C10164.26 (13)
O1i—Cu1—O1—P1147 (6)C14—C9—C10—C110.8 (3)
C1—P2—O2—Cu140.14 (11)P1—C9—C10—C11170.67 (14)
C21—P2—O2—Cu1158.90 (8)C9—C10—C11—C120.0 (3)
C15—P2—O2—Cu183.36 (10)C10—C11—C12—C130.9 (3)
O2i—Cu1—O2—P2122 (9)C11—C12—C13—C141.0 (3)
O1i—Cu1—O2—P2174.51 (9)C12—C13—C14—C90.2 (3)
O1—Cu1—O2—P25.49 (9)C10—C9—C14—C130.7 (3)
O2—P2—C1—C2135.75 (13)P1—C9—C14—C13170.41 (15)
C21—P2—C1—C215.74 (16)O2—P2—C15—C16154.64 (15)
C15—P2—C1—C2102.24 (15)C1—P2—C15—C1630.03 (18)
O2—P2—C1—P149.44 (11)C21—P2—C15—C1687.11 (17)
C21—P2—C1—P1169.45 (9)O2—P2—C15—C2024.48 (16)
C15—P2—C1—P172.57 (11)C1—P2—C15—C20149.10 (14)
O1—P1—C1—C2179.75 (13)C21—P2—C15—C2093.76 (15)
C9—P1—C1—C259.30 (15)C20—C15—C16—C170.4 (3)
C3—P1—C1—C260.54 (16)P2—C15—C16—C17179.55 (19)
O1—P1—C1—P25.31 (11)C15—C16—C17—C181.2 (4)
C9—P1—C1—P2125.76 (9)C16—C17—C18—C191.0 (4)
C3—P1—C1—P2114.40 (10)C17—C18—C19—C200.1 (4)
P2—C1—C2—N1178 (100)C18—C19—C20—C150.7 (3)
P1—C1—C2—N14 (4)C16—C15—C20—C190.5 (3)
O1—P1—C3—C46.89 (17)P2—C15—C20—C19178.61 (14)
C1—P1—C3—C4126.36 (15)O2—P2—C21—C22113.92 (15)
C9—P1—C3—C4112.80 (15)C1—P2—C21—C22123.65 (15)
O1—P1—C3—C8170.65 (15)C15—P2—C21—C223.87 (17)
C1—P1—C3—C851.19 (18)O2—P2—C21—C2664.13 (14)
C9—P1—C3—C869.66 (17)C1—P2—C21—C2658.30 (14)
C8—C3—C4—C50.1 (3)C15—P2—C21—C26178.08 (13)
P1—C3—C4—C5177.50 (15)C26—C21—C22—C230.9 (3)
C3—C4—C5—C60.5 (3)P2—C21—C22—C23178.91 (15)
C4—C5—C6—C70.6 (3)C21—C22—C23—C240.1 (3)
C5—C6—C7—C80.3 (4)C22—C23—C24—C251.0 (3)
C6—C7—C8—C30.3 (4)C23—C24—C25—C260.9 (3)
C4—C3—C8—C70.4 (3)C24—C25—C26—C210.2 (3)
P1—C3—C8—C7177.14 (18)C22—C21—C26—C251.1 (3)
O1—P1—C9—C1494.03 (15)P2—C21—C26—C25179.18 (14)
Symmetry code: (i) x, y, z+1.

Experimental details

Crystal data
Chemical formula[Cu(C26H20NO2P2)2]
Mr944.28
Crystal system, space groupMonoclinic, P21/n
Temperature (K)173
a, b, c (Å)9.5917 (7), 25.8793 (19), 9.6648 (7)
β (°) 111.526 (1)
V3)2231.7 (3)
Z2
Radiation typeMo Kα
µ (mm1)0.68
Crystal size (mm)0.33 × 0.23 × 0.12
Data collection
DiffractometerBruker APEXII CCD
Absorption correctionMulti-scan
(SADABS; Bruker, 2009)
Tmin, Tmax0.807, 0.920
No. of measured, independent and
observed [I > 2σ(I)] reflections
43689, 5640, 4832
Rint0.036
(sin θ/λ)max1)0.683
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.033, 0.086, 1.03
No. of reflections5640
No. of parameters286
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.49, 0.32

Computer programs: COSMO (Bruker, 2009), APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

 

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