Tetra-μ-methacryl­ato-κ⁸O:O′-bis­[(pyridine-κN)copper(II)]

In the title carboxyl­ate-bridged binuclear copper complex, [Cu₂{CH₂C(CH₃)COO}₄(C₅H₅N)₂], the Cu atoms are bridged by four bidentate methacryl­ate groups. The asymmetric unit consists of two half-molecules, each molecule having inversion symmetry. The Cu...Cu separations are 2.6181 (8) and 2.6442 (10) Å. All bond lengths and angles are normal.

Key indicators

• Single-crystal X-ray study
• T = 263 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.033
• wR factor = 0.079
• Data-to-parameter ratio = 15.4

checkCIF/PLATON results

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Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT241_ALERT_2_C Check High   U(eq) as Compared to Neighbors  for         O5

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   2 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
   1 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
   0 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97.

tetra-µ-methacrylato-κ⁸O:O'-bis[(pyridine-κN)copper(II)]

Crystal data

[Cu2(C4H5O2)4(C5H5N)2]	Z = 2
Mr = 625.60	F(000) = 644
Triclinic, P1	Dx = 1.482 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71069 Å
a = 8.8214 (18) Å	Cell parameters from 7999 reflections
b = 9.936 (2) Å	θ = 1.3–27.4°
c = 16.392 (3) Å	µ = 1.57 mm^−1
α = 100.57 (3)°	T = 263 K
β = 92.76 (3)°	Prism, green
γ = 95.88 (3)°	0.28 × 0.25 × 0.24 mm
V = 1401.6 (5) Å^3

Data collection

Rigaku R-AXIS RAPID diffractometer	5342 independent reflections
Radiation source: fine-focus sealed tube	4326 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.027
Detector resolution: 10.00 pixels mm^-1	θmax = 25.8°, θmin = 2.2°
ω scans	h = −10→10
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	k = −12→12
Tmin = 0.651, Tmax = 0.687	l = −20→20
11151 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.079	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0412P)^2 + 0.4712P] where P = (Fo^2 + 2Fc^2)/3
5342 reflections	(Δ/σ)max = 0.002
347 parameters	Δρmax = 0.47 e Å^−3
0 restraints	Δρmin = −0.33 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
Cu1	0.51913 (3)	1.00645 (3)	0.422056 (18)	0.03561 (9)
Cu2	0.40488 (3)	0.58381 (3)	0.035469 (17)	0.03646 (9)
O1	0.4243 (2)	0.81398 (18)	0.38983 (11)	0.0452 (4)
O2	0.3948 (2)	0.80418 (18)	0.52283 (11)	0.0480 (4)
O3	0.71429 (19)	0.93420 (19)	0.44188 (11)	0.0458 (4)
O4	0.68642 (19)	0.93016 (19)	0.57608 (11)	0.0460 (4)
O5	0.2992 (2)	0.41118 (19)	0.05876 (13)	0.0546 (5)
O6	0.4613 (2)	0.26984 (18)	0.00045 (12)	0.0484 (4)
O7	0.2926 (2)	0.54708 (19)	−0.07518 (11)	0.0466 (4)
O8	0.4521 (2)	0.4040 (2)	−0.13344 (11)	0.0542 (5)
N1	0.5630 (2)	1.0591 (2)	0.30338 (13)	0.0398 (5)
N2	0.2447 (2)	0.70570 (19)	0.10274 (12)	0.0358 (4)
C1	0.5143 (3)	1.1740 (3)	0.28589 (17)	0.0493 (7)
H1	0.4543	1.2226	0.3233	0.059*
C2	0.5481 (4)	1.2240 (3)	0.21567 (18)	0.0552 (7)
H2	0.5113	1.3042	0.2056	0.066*
C3	0.6372 (4)	1.1536 (3)	0.16050 (19)	0.0609 (8)
H3	0.6631	1.1856	0.1126	0.073*
C4	0.6875 (4)	1.0351 (4)	0.17737 (19)	0.0629 (8)
H4	0.7471	0.9846	0.1406	0.075*
C5	0.6488 (3)	0.9919 (3)	0.24926 (17)	0.0486 (7)
H5	0.6845	0.9118	0.2605	0.058*
C6	0.3849 (3)	0.7518 (3)	0.44682 (17)	0.0397 (6)
C7	0.3200 (3)	0.6028 (3)	0.42404 (19)	0.0510 (7)
C8	0.2954 (4)	0.5425 (3)	0.3430 (2)	0.0709 (9)
H8A	0.2552	0.4504	0.3283	0.085*
H8B	0.3186	0.5931	0.3019	0.085*
C9	0.2869 (5)	0.5312 (3)	0.4923 (2)	0.0857 (12)
H9A	0.1997	0.5645	0.5188	0.129*
H9B	0.3735	0.5479	0.5320	0.129*
H9C	0.2656	0.4341	0.4710	0.129*
C10	0.7575 (3)	0.9086 (2)	0.51083 (17)	0.0388 (6)
C11	0.9062 (3)	0.8476 (3)	0.51738 (19)	0.0468 (7)
C12	0.9764 (3)	0.8066 (3)	0.4483 (2)	0.0589 (8)
H12A	1.0681	0.7687	0.4515	0.071*
H12B	0.9336	0.8160	0.3969	0.071*
C13	0.9670 (4)	0.8360 (3)	0.6007 (2)	0.0670 (9)
H13A	1.0591	0.7920	0.5960	0.100*
H13B	0.8928	0.7820	0.6259	0.100*
H13C	0.9889	0.9262	0.6346	0.100*
C14	0.3442 (3)	0.2948 (3)	0.03943 (15)	0.0411 (6)
C15	0.2502 (3)	0.1768 (3)	0.06482 (17)	0.0475 (6)
C16	0.1229 (4)	0.2108 (4)	0.1175 (3)	0.0769 (10)
H16A	0.0672	0.1273	0.1267	0.115*
H16B	0.0558	0.2614	0.0901	0.115*
H16C	0.1629	0.2659	0.1700	0.115*
C17	0.2844 (4)	0.0492 (3)	0.0408 (2)	0.0618 (8)
H17A	0.2271	−0.0239	0.0572	0.074*
H17B	0.3657	0.0329	0.0076	0.074*
C18	0.3379 (3)	0.4690 (3)	−0.13624 (15)	0.0396 (6)
C19	0.2504 (3)	0.4542 (3)	−0.21878 (17)	0.0457 (6)
C20	0.3060 (4)	0.3874 (3)	−0.28612 (18)	0.0607 (8)
H20A	0.2548	0.3801	−0.3379	0.073*
H20B	0.3964	0.3478	−0.2816	0.073*
C21	0.1065 (3)	0.5200 (4)	−0.2214 (2)	0.0664 (9)
H21A	0.0598	0.4988	−0.2770	0.100*
H21B	0.1292	0.6181	−0.2045	0.100*
H21C	0.0378	0.4856	−0.1844	0.100*
C22	0.2842 (3)	0.7825 (3)	0.17776 (16)	0.0442 (6)
H22	0.3850	0.7884	0.1986	0.053*
C23	0.1850 (3)	0.8529 (3)	0.22580 (17)	0.0507 (7)
H23	0.2181	0.9055	0.2777	0.061*
C24	0.0365 (3)	0.8448 (3)	0.19631 (18)	0.0528 (7)
H24	−0.0334	0.8917	0.2278	0.063*
C25	−0.0082 (3)	0.7658 (3)	0.11882 (18)	0.0529 (7)
H25	−0.1087	0.7586	0.0970	0.063*
C26	0.0987 (3)	0.6984 (3)	0.07479 (16)	0.0446 (6)
H26	0.0680	0.6449	0.0228	0.054*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cu1	0.03375 (16)	0.03844 (17)	0.03664 (17)	0.00445 (12)	0.00356 (12)	0.01184 (13)
Cu2	0.04371 (18)	0.03328 (16)	0.03530 (17)	0.01045 (13)	0.00662 (13)	0.00977 (12)
O1	0.0463 (10)	0.0411 (10)	0.0464 (10)	0.0008 (8)	−0.0002 (8)	0.0071 (8)
O2	0.0535 (11)	0.0400 (10)	0.0500 (11)	−0.0022 (8)	0.0042 (9)	0.0110 (8)
O3	0.0345 (9)	0.0548 (11)	0.0503 (11)	0.0096 (8)	0.0055 (8)	0.0125 (9)
O4	0.0389 (9)	0.0545 (11)	0.0478 (11)	0.0113 (8)	0.0005 (8)	0.0153 (9)
O5	0.0661 (12)	0.0385 (10)	0.0655 (13)	0.0112 (9)	0.0254 (10)	0.0181 (9)
O6	0.0545 (11)	0.0365 (10)	0.0563 (11)	0.0060 (8)	0.0131 (10)	0.0117 (8)
O7	0.0492 (10)	0.0489 (11)	0.0425 (10)	0.0157 (9)	0.0011 (8)	0.0059 (8)
O8	0.0595 (12)	0.0670 (13)	0.0393 (10)	0.0307 (10)	−0.0001 (9)	0.0065 (9)
N1	0.0413 (11)	0.0416 (12)	0.0391 (11)	0.0054 (9)	0.0034 (9)	0.0138 (9)
N2	0.0386 (11)	0.0315 (10)	0.0378 (11)	0.0046 (8)	0.0023 (9)	0.0081 (8)
C1	0.0631 (18)	0.0436 (15)	0.0445 (15)	0.0135 (13)	0.0066 (13)	0.0119 (12)
C2	0.075 (2)	0.0427 (16)	0.0511 (16)	0.0069 (14)	−0.0006 (15)	0.0189 (13)
C3	0.073 (2)	0.071 (2)	0.0466 (16)	0.0109 (17)	0.0082 (15)	0.0304 (15)
C4	0.072 (2)	0.077 (2)	0.0494 (17)	0.0308 (17)	0.0204 (15)	0.0228 (16)
C5	0.0526 (16)	0.0515 (16)	0.0478 (15)	0.0154 (13)	0.0072 (13)	0.0192 (13)
C6	0.0303 (12)	0.0374 (13)	0.0516 (16)	0.0054 (10)	−0.0039 (11)	0.0100 (12)
C7	0.0432 (15)	0.0387 (15)	0.0700 (19)	0.0027 (12)	−0.0009 (14)	0.0093 (14)
C8	0.078 (2)	0.0464 (18)	0.079 (2)	−0.0090 (16)	−0.0033 (19)	−0.0013 (16)
C9	0.114 (3)	0.0471 (19)	0.094 (3)	−0.0137 (19)	0.007 (2)	0.0199 (18)
C10	0.0313 (12)	0.0296 (12)	0.0545 (16)	0.0011 (10)	0.0012 (12)	0.0072 (11)
C11	0.0301 (13)	0.0345 (13)	0.0731 (19)	0.0008 (10)	−0.0038 (13)	0.0063 (13)
C12	0.0375 (15)	0.0569 (18)	0.080 (2)	0.0121 (13)	0.0084 (15)	0.0019 (16)
C13	0.0553 (18)	0.063 (2)	0.083 (2)	0.0194 (15)	−0.0124 (17)	0.0135 (17)
C14	0.0509 (15)	0.0374 (14)	0.0358 (13)	0.0024 (12)	−0.0004 (12)	0.0114 (11)
C15	0.0527 (16)	0.0437 (15)	0.0489 (15)	0.0020 (12)	0.0048 (13)	0.0177 (12)
C16	0.078 (2)	0.065 (2)	0.099 (3)	0.0097 (18)	0.038 (2)	0.035 (2)
C17	0.080 (2)	0.0412 (16)	0.066 (2)	−0.0015 (15)	0.0113 (17)	0.0174 (14)
C18	0.0435 (14)	0.0383 (13)	0.0392 (14)	0.0034 (11)	0.0029 (11)	0.0138 (11)
C19	0.0472 (15)	0.0455 (15)	0.0445 (15)	0.0013 (12)	−0.0025 (12)	0.0124 (12)
C20	0.071 (2)	0.066 (2)	0.0422 (16)	0.0059 (16)	−0.0076 (15)	0.0051 (14)
C21	0.0581 (19)	0.078 (2)	0.066 (2)	0.0172 (17)	−0.0082 (16)	0.0188 (17)
C22	0.0359 (13)	0.0466 (15)	0.0481 (15)	0.0066 (11)	−0.0032 (12)	0.0039 (12)
C23	0.0529 (16)	0.0553 (17)	0.0412 (14)	0.0147 (13)	−0.0014 (13)	−0.0015 (12)
C24	0.0439 (15)	0.0651 (19)	0.0506 (16)	0.0180 (14)	0.0106 (13)	0.0057 (14)
C25	0.0346 (14)	0.0624 (18)	0.0604 (18)	0.0076 (13)	−0.0017 (13)	0.0083 (15)
C26	0.0485 (15)	0.0401 (14)	0.0428 (14)	0.0041 (12)	−0.0048 (12)	0.0035 (11)

Geometric parameters (Å, º)

Cu1—O1	1.9735 (19)	C8—H8A	0.9300
Cu1—O2^i	1.9875 (19)	C8—H8B	0.9300
Cu1—O3	1.9672 (18)	C9—H9A	0.9600
Cu1—O4^i	1.9794 (18)	C9—H9B	0.9600
Cu1—N1	2.147 (2)	C9—H9C	0.9600
Cu2—O5	1.9757 (19)	C10—C11	1.508 (3)
Cu2—O6^ii	1.9710 (19)	C11—C12	1.335 (4)
Cu2—O7	1.9784 (18)	C11—C13	1.472 (4)
Cu2—O8^ii	1.9717 (19)	C12—H12A	0.9300
Cu2—N2	2.165 (2)	C12—H12B	0.9300
O1—C6	1.255 (3)	C13—H13A	0.9600
O2—C6	1.254 (3)	C13—H13B	0.9600
O2—Cu1^i	1.9875 (19)	C13—H13C	0.9600
O3—C10	1.253 (3)	C14—C15	1.500 (4)
O4—C10	1.261 (3)	C15—C17	1.326 (4)
O4—Cu1^i	1.9794 (18)	C15—C16	1.479 (4)
O5—C14	1.252 (3)	C16—H16A	0.9600
O6—C14	1.263 (3)	C16—H16B	0.9600
O6—Cu2^ii	1.9710 (19)	C16—H16C	0.9600
O7—C18	1.257 (3)	C17—H17A	0.9300
O8—C18	1.254 (3)	C17—H17B	0.9300
O8—Cu2^ii	1.9717 (19)	C18—C19	1.501 (3)
N1—C5	1.326 (3)	C19—C20	1.323 (4)
N1—C1	1.333 (3)	C19—C21	1.488 (4)
N2—C22	1.333 (3)	C20—H20A	0.9300
N2—C26	1.337 (3)	C20—H20B	0.9300
C1—C2	1.369 (4)	C21—H21A	0.9600
C1—H1	0.9300	C21—H21B	0.9600
C2—C3	1.369 (4)	C21—H21C	0.9600
C2—H2	0.9300	C22—C23	1.366 (4)
C3—C4	1.369 (4)	C22—H22	0.9300
C3—H3	0.9300	C23—C24	1.363 (4)
C4—C5	1.373 (4)	C23—H23	0.9300
C4—H4	0.9300	C24—C25	1.381 (4)
C5—H5	0.9300	C24—H24	0.9300
C6—C7	1.504 (4)	C25—C26	1.370 (4)
C7—C8	1.350 (4)	C25—H25	0.9300
C7—C9	1.457 (5)	C26—H26	0.9300
O1—Cu1—O2^i	168.63 (8)	H9A—C9—H9C	109.5
O1—Cu1—O3	87.96 (8)	H9B—C9—H9C	109.5
O1—Cu1—O4^i	89.68 (8)	O3—C10—O4	125.2 (2)
O1—Cu1—N1	101.92 (8)	O3—C10—C11	118.1 (2)
O2^i—Cu1—N1	89.42 (8)	O4—C10—C11	116.7 (2)
O3—Cu1—O2^i	91.55 (8)	C12—C11—C13	123.0 (3)
O3—Cu1—O4^i	168.53 (8)	C12—C11—C10	119.2 (3)
O3—Cu1—N1	97.32 (8)	C13—C11—C10	117.8 (3)
O4^i—Cu1—O2^i	88.55 (8)	C11—C12—H12A	120.0
O4^i—Cu1—N1	94.15 (8)	C11—C12—H12B	120.0
O5—Cu2—O7	89.42 (9)	H12A—C12—H12B	120.0
O5—Cu2—N2	91.80 (8)	C11—C13—H13A	109.5
O6^ii—Cu2—O5	167.97 (8)	C11—C13—H13B	109.5
O6^ii—Cu2—O7	88.84 (8)	H13A—C13—H13B	109.5
O6^ii—Cu2—N2	100.23 (8)	C11—C13—H13C	109.5
O7—Cu2—N2	97.60 (8)	H13A—C13—H13C	109.5
O8^ii—Cu2—O5	89.88 (9)	H13B—C13—H13C	109.5
O8^ii—Cu2—O6^ii	89.31 (9)	O5—C14—O6	125.1 (2)
O8^ii—Cu2—O7	167.79 (7)	O5—C14—C15	116.7 (2)
O8^ii—Cu2—N2	94.61 (8)	O6—C14—C15	118.1 (2)
C6—O1—Cu1	117.79 (16)	C17—C15—C16	123.1 (3)
C6—O2—Cu1^i	128.39 (17)	C17—C15—C14	119.9 (3)
C10—O3—Cu1	122.99 (17)	C16—C15—C14	116.9 (2)
C10—O4—Cu1^i	122.83 (16)	C15—C16—H16A	109.5
C14—O5—Cu2	124.80 (18)	C15—C16—H16B	109.5
C14—O6—Cu2^ii	122.04 (16)	H16A—C16—H16B	109.5
C18—O7—Cu2	121.52 (16)	C15—C16—H16C	109.5
C18—O8—Cu2^ii	125.78 (17)	H16A—C16—H16C	109.5
C5—N1—C1	117.2 (2)	H16B—C16—H16C	109.5
C5—N1—Cu1	123.94 (18)	C15—C17—H17A	120.0
C1—N1—Cu1	118.50 (18)	C15—C17—H17B	120.0
C22—N2—C26	116.6 (2)	H17A—C17—H17B	120.0
C22—N2—Cu2	121.18 (16)	O8—C18—O7	124.8 (2)
C26—N2—Cu2	121.92 (16)	O8—C18—C19	117.6 (2)
N1—C1—C2	123.4 (3)	O7—C18—C19	117.6 (2)
N1—C1—H1	118.3	C20—C19—C21	122.8 (3)
C2—C1—H1	118.3	C20—C19—C18	119.0 (3)
C1—C2—C3	118.7 (3)	C21—C19—C18	118.1 (2)
C1—C2—H2	120.6	C19—C20—H20A	120.0
C3—C2—H2	120.6	C19—C20—H20B	120.0
C2—C3—C4	118.6 (3)	H20A—C20—H20B	120.0
C2—C3—H3	120.7	C19—C21—H21A	109.5
C4—C3—H3	120.7	C19—C21—H21B	109.5
C3—C4—C5	119.1 (3)	H21A—C21—H21B	109.5
C3—C4—H4	120.4	C19—C21—H21C	109.5
C5—C4—H4	120.4	H21A—C21—H21C	109.5
N1—C5—C4	122.9 (3)	H21B—C21—H21C	109.5
N1—C5—H5	118.5	N2—C22—C23	123.8 (2)
C4—C5—H5	118.5	N2—C22—H22	118.1
O2—C6—O1	125.1 (2)	C23—C22—H22	118.1
O2—C6—C7	116.2 (2)	C24—C23—C22	118.9 (3)
O1—C6—C7	118.7 (2)	C24—C23—H23	120.6
C8—C7—C9	123.5 (3)	C22—C23—H23	120.6
C8—C7—C6	119.4 (3)	C23—C24—C25	118.8 (3)
C9—C7—C6	117.1 (3)	C23—C24—H24	120.6
C7—C8—H8A	120.0	C25—C24—H24	120.6
C7—C8—H8B	120.0	C26—C25—C24	118.5 (3)
H8A—C8—H8B	120.0	C26—C25—H25	120.8
C7—C9—H9A	109.5	C24—C25—H25	120.8
C7—C9—H9B	109.5	N2—C26—C25	123.4 (2)
H9A—C9—H9B	109.5	N2—C26—H26	118.3
C7—C9—H9C	109.5	C25—C26—H26	118.3

Symmetry codes: (i) −x+1, −y+2, −z+1; (ii) −x+1, −y+1, −z.