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In the title compound, [Cu2(C15H11ClN2O3)2(C5H5N)2]·2CH3OH, the coordination geometry of the metal centre can be described as square pyramidal. Pairs of penta­coordinated metal centres are bridged by symmetry-related phenolate O atoms about the inversion centre at (1 \over 2, 0, 1 \over 2), resulting in a binuclear metal cluster via edge-sharing.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270113005118/ov3024sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270113005118/ov3024Isup2.hkl
Contains datablock I

CCDC reference: 934597

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SMART (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenberg & Putz, 2010); software used to prepare material for publication: SHELXTL (Bruker, 2003).

Bis[µ-2-({2-[2-(2-chlorophenoxy)-1-oxidoethylidene]hydrazinylidene}methyl)phenolato]bis[pyridinecopper(II)] methanol disolvate top
Crystal data top
[Cu2(C15H11ClN2O3)2(C5H5N)2]·2CH4OZ = 1
Mr = 954.78F(000) = 490
Triclinic, P1Dx = 1.495 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.5570 (16) ÅCell parameters from 13246 reflections
b = 12.223 (3) Åθ = 12–18°
c = 12.681 (3) ŵ = 1.19 mm1
α = 111.615 (3)°T = 298 K
β = 92.294 (4)°Block, green
γ = 101.130 (4)°0.33 × 0.30 × 0.26 mm
V = 1060.5 (4) Å3
Data collection top
Bruker SMART CCD area-detector
diffractometer
4837 independent reflections
Radiation source: fine-focus sealed tube4282 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.023
Detector resolution: 8.33 pixels mm-1θmax = 27.6°, θmin = 1.7°
phi and ω scansh = 99
Absorption correction: multi-scan
(SADABS; Bruker, 2007)
k = 1515
Tmin = 0.58, Tmax = 0.65l = 1616
13246 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)] = 0.032Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.114H-atom parameters constrained
S = 1.06 w = 1/[σ2(Fo2) + (0.081P)2 + 0.1044P]
where P = (Fo2 + 2Fc2)/3
4837 reflections(Δ/σ)max = 0.001
272 parametersΔρmax = 0.47 e Å3
0 restraintsΔρmin = 0.36 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
Cu10.37590 (3)0.061224 (18)0.603002 (17)0.03378 (10)
Cl10.77810 (12)0.66071 (7)0.85857 (8)0.0776 (2)
O10.3539 (2)0.10268 (12)0.49997 (11)0.0386 (3)
O20.63343 (18)0.44349 (11)0.89247 (12)0.0428 (3)
O30.4260 (2)0.22579 (12)0.72112 (11)0.0406 (3)
N10.4589 (2)0.02782 (14)0.73203 (13)0.0351 (3)
N20.5186 (2)0.13030 (15)0.83313 (13)0.0404 (4)
N30.2259 (2)0.09911 (15)0.49099 (14)0.0378 (3)
C10.4044 (3)0.18859 (17)0.64073 (16)0.0362 (4)
C20.4012 (4)0.29565 (19)0.66065 (19)0.0497 (5)
H20.43780.28970.73380.060*
C30.3463 (4)0.4065 (2)0.5758 (2)0.0648 (7)
H30.34400.47560.59090.078*
C40.2933 (4)0.4158 (2)0.4656 (2)0.0648 (8)
H40.25680.49150.40690.078*
C50.2946 (4)0.31361 (19)0.44298 (18)0.0493 (5)
H50.25690.32200.36920.059*
C60.3513 (3)0.19738 (16)0.52836 (15)0.0349 (4)
C70.4607 (3)0.07590 (18)0.73625 (16)0.0380 (4)
H70.50110.07750.80580.046*
C80.4931 (3)0.22580 (17)0.81570 (16)0.0352 (4)
C90.5449 (3)0.34423 (17)0.91923 (17)0.0410 (4)
H9A0.43600.36250.95320.049*
H9B0.62480.33480.97550.049*
C100.8075 (3)0.44625 (18)0.86667 (15)0.0394 (4)
C110.9012 (3)0.3566 (2)0.85754 (19)0.0482 (5)
H110.84640.28910.87150.058*
C121.0772 (3)0.3678 (3)0.8275 (2)0.0607 (6)
H121.13860.30690.82050.073*
C131.1611 (4)0.4679 (3)0.8082 (2)0.0705 (8)
H131.27870.47480.78840.085*
C141.0693 (4)0.5583 (3)0.8183 (2)0.0648 (7)
H141.12560.62630.80570.078*
C150.8950 (3)0.5475 (2)0.84694 (19)0.0487 (5)
C160.1444 (3)0.0133 (2)0.39119 (19)0.0464 (5)
H160.15280.06590.37530.056*
C170.0476 (3)0.0381 (3)0.3103 (2)0.0583 (6)
H170.00780.02360.24180.070*
C180.0351 (4)0.1557 (3)0.3331 (2)0.0630 (7)
H180.02700.17450.27960.076*
C190.1153 (4)0.2441 (3)0.4356 (3)0.0626 (7)
H190.10640.32370.45360.075*
C200.2104 (3)0.2129 (2)0.5123 (2)0.0502 (5)
H200.26570.27340.58160.060*
O40.6731 (5)0.1342 (3)1.0437 (2)0.1056 (9)
H4A0.64260.14750.98750.158*
C210.7959 (6)0.0597 (5)1.0163 (4)0.1166 (16)
H21A0.84020.05740.94580.175*
H21B0.73650.02041.00810.175*
H21C0.89590.09061.07610.175*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cu10.04382 (16)0.02795 (14)0.02753 (14)0.01151 (10)0.00380 (9)0.00664 (10)
Cl10.0898 (5)0.0568 (4)0.0986 (6)0.0219 (4)0.0243 (4)0.0400 (4)
O10.0572 (8)0.0276 (6)0.0293 (6)0.0104 (6)0.0048 (6)0.0087 (5)
O20.0394 (8)0.0315 (7)0.0488 (9)0.0094 (6)0.0070 (6)0.0045 (6)
O30.0547 (8)0.0310 (7)0.0330 (7)0.0150 (6)0.0044 (6)0.0063 (5)
N10.0414 (8)0.0308 (7)0.0280 (7)0.0064 (6)0.0018 (6)0.0065 (6)
N20.0504 (10)0.0325 (8)0.0291 (8)0.0053 (7)0.0009 (7)0.0038 (6)
N30.0380 (8)0.0397 (8)0.0377 (8)0.0119 (7)0.0068 (6)0.0154 (7)
C10.0431 (10)0.0308 (9)0.0347 (9)0.0073 (7)0.0058 (8)0.0127 (7)
C20.0726 (15)0.0390 (11)0.0418 (11)0.0123 (10)0.0078 (10)0.0203 (9)
C30.110 (2)0.0333 (11)0.0540 (13)0.0129 (12)0.0114 (14)0.0213 (10)
C40.111 (2)0.0283 (10)0.0442 (12)0.0050 (12)0.0089 (13)0.0073 (9)
C50.0750 (16)0.0332 (10)0.0333 (10)0.0063 (10)0.0060 (10)0.0084 (8)
C60.0416 (10)0.0303 (9)0.0314 (9)0.0068 (7)0.0082 (7)0.0104 (7)
C70.0443 (10)0.0377 (10)0.0310 (9)0.0076 (8)0.0027 (7)0.0129 (8)
C80.0343 (9)0.0335 (9)0.0317 (8)0.0078 (7)0.0078 (7)0.0050 (7)
C90.0439 (10)0.0331 (9)0.0354 (9)0.0066 (8)0.0097 (8)0.0016 (8)
C100.0390 (10)0.0382 (10)0.0285 (8)0.0060 (8)0.0010 (7)0.0003 (7)
C110.0430 (11)0.0472 (12)0.0437 (11)0.0118 (9)0.0003 (9)0.0051 (9)
C120.0428 (12)0.0722 (17)0.0537 (14)0.0203 (12)0.0025 (10)0.0057 (12)
C130.0428 (13)0.099 (2)0.0538 (15)0.0110 (14)0.0116 (11)0.0124 (15)
C140.0574 (15)0.0768 (18)0.0496 (13)0.0031 (13)0.0112 (11)0.0208 (13)
C150.0527 (12)0.0481 (12)0.0384 (10)0.0078 (10)0.0047 (9)0.0105 (9)
C160.0462 (11)0.0496 (12)0.0417 (11)0.0110 (9)0.0017 (9)0.0156 (9)
C170.0514 (13)0.0764 (17)0.0459 (12)0.0139 (12)0.0033 (10)0.0234 (12)
C180.0500 (13)0.089 (2)0.0691 (16)0.0184 (13)0.0008 (12)0.0511 (16)
C190.0623 (15)0.0587 (15)0.0825 (19)0.0225 (12)0.0079 (14)0.0406 (14)
C200.0548 (13)0.0438 (11)0.0541 (13)0.0156 (10)0.0031 (10)0.0193 (10)
O40.160 (3)0.102 (2)0.0537 (13)0.0246 (19)0.0007 (15)0.0323 (13)
C210.104 (3)0.151 (4)0.084 (3)0.030 (3)0.017 (2)0.035 (3)
Geometric parameters (Å, º) top
Cu1—O11.9167 (13)C9—H9A0.9700
Cu1—N11.9356 (16)C9—H9B0.9700
Cu1—O31.9683 (14)C10—C111.388 (3)
Cu1—N32.0188 (17)C10—C151.399 (3)
Cl1—C151.746 (3)C11—C121.393 (3)
O1—C61.330 (2)C11—H110.9300
O2—C101.365 (2)C12—C131.376 (4)
O2—C91.429 (2)C12—H120.9300
O3—C81.283 (2)C13—C141.385 (5)
N1—C71.291 (3)C13—H130.9300
N1—N21.403 (2)C14—C151.375 (4)
N2—C81.312 (3)C14—H140.9300
N3—C161.338 (3)C16—C171.391 (3)
N3—C201.345 (3)C16—H160.9300
C1—C21.417 (3)C17—C181.380 (4)
C1—C61.424 (3)C17—H170.9300
C1—C71.431 (3)C18—C191.370 (4)
C2—C31.356 (3)C18—H180.9300
C2—H20.9300C19—C201.390 (3)
C3—C41.396 (4)C19—H190.9300
C3—H30.9300C20—H200.9300
C4—C51.379 (3)O4—C211.389 (5)
C4—H40.9300O4—H4A0.8200
C5—C61.403 (3)C21—H21A0.9600
C5—H50.9300C21—H21B0.9600
C7—H70.9300C21—H21C0.9600
C8—C91.521 (3)
O1—Cu1—N192.16 (6)O2—C9—H9B108.9
O1—Cu1—O3171.97 (6)C8—C9—H9B108.9
N1—Cu1—O380.88 (6)H9A—C9—H9B107.7
O1—Cu1—N392.97 (7)O2—C10—C11125.12 (19)
N1—Cu1—N3163.82 (7)O2—C10—C15116.38 (19)
O3—Cu1—N394.80 (7)C11—C10—C15118.5 (2)
C6—O1—Cu1126.52 (12)C10—C11—C12120.0 (2)
C10—O2—C9117.34 (16)C10—C11—H11120.0
C8—O3—Cu1109.78 (12)C12—C11—H11120.0
C7—N1—N2117.42 (16)C13—C12—C11120.7 (3)
C7—N1—Cu1127.99 (13)C13—C12—H12119.6
N2—N1—Cu1114.56 (12)C11—C12—H12119.6
C8—N2—N1109.07 (15)C12—C13—C14119.6 (2)
C16—N3—C20117.57 (19)C12—C13—H13120.2
C16—N3—Cu1121.48 (15)C14—C13—H13120.2
C20—N3—Cu1120.90 (15)C15—C14—C13120.1 (3)
C2—C1—C6119.23 (18)C15—C14—H14120.0
C2—C1—C7117.62 (18)C13—C14—H14120.0
C6—C1—C7123.14 (17)C14—C15—C10121.1 (2)
C3—C2—C1121.7 (2)C14—C15—Cl1120.2 (2)
C3—C2—H2119.1C10—C15—Cl1118.71 (18)
C1—C2—H2119.1N3—C16—C17122.6 (2)
C2—C3—C4119.3 (2)N3—C16—H16118.7
C2—C3—H3120.3C17—C16—H16118.7
C4—C3—H3120.3C18—C17—C16119.0 (2)
C5—C4—C3120.6 (2)C18—C17—H17120.5
C5—C4—H4119.7C16—C17—H17120.5
C3—C4—H4119.7C19—C18—C17119.1 (2)
C4—C5—C6121.8 (2)C19—C18—H18120.5
C4—C5—H5119.1C17—C18—H18120.5
C6—C5—H5119.1C18—C19—C20118.8 (2)
O1—C6—C5118.63 (17)C18—C19—H19120.6
O1—C6—C1124.02 (16)C20—C19—H19120.6
C5—C6—C1117.35 (17)N3—C20—C19122.9 (2)
N1—C7—C1124.19 (17)N3—C20—H20118.5
N1—C7—H7117.9C19—C20—H20118.5
C1—C7—H7117.9C21—O4—H4A109.5
O3—C8—N2125.54 (17)O4—C21—H21A109.5
O3—C8—C9119.02 (17)O4—C21—H21B109.5
N2—C8—C9115.42 (17)H21A—C21—H21B109.5
O2—C9—C8113.26 (16)O4—C21—H21C109.5
O2—C9—H9A108.9H21A—C21—H21C109.5
C8—C9—H9A108.9H21B—C21—H21C109.5
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O4—H4A···N20.822.062.851 (3)163
 

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