catena-Poly[[aqua­(4,4′-dimethyl-2,2′-bipyridine)copper(II)]-μ-fumarato-κ²O,O′:κ²O′′,O′′′-[aqua­(4,4′-dimethyl-2,2′-bipyridine)copper(II)]-μ-fumarato-κO:κO′]

The title compound, [Cu(C₄H₂O₄)(C₁₂H₁₂N₂)(H₂O)]_n, has a neutral polymeric chain structure in which fumarate ligands link the Cu atoms; the chains are then linked together by hydrogen bonds. The unique Cu^II ion exhibits a distorted octa­hedral coordination geometry defined by three O atoms of two different centrosymmetric fumarate ligands, two N atoms from the chelating dmbpy ligand (dmbpy is 4,4′-dimethyl-2,2′-bipyridine) and one water mol­ecule. The fumarate ligands show two types of coordination modes, viz. bis-bidentate-chelating and bis-mono-O-carboxyl­ate bridging.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.039
• wR factor = 0.103
• Data-to-parameter ratio = 12.9

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature .        293 K
PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety        C15
PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety        C16
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          2
PLAT731_ALERT_1_C Bond    Calc     0.84(4), Rep   0.842(10) ......       4.00 su-Rat
              O1W  -HW1A    1.555   1.555
PLAT731_ALERT_1_C Bond    Calc     0.84(4), Rep   0.845(10) ......       4.00 su-Rat
              O1W  -HW1B    1.555   1.555

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   6 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 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
   3 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1998); software used to prepare material for publication: SHELXTL.

catena-Poly[[aqua(4,4'-dimethyl-2,2'-bipyridine)copper(II)]-µ-fumarato]

Crystal data

[Cu(C4H2O4)(C12H12N2)(H2O)]	Z = 2
Mr = 379.85	F(000) = 390
Triclinic, P1	Dx = 1.572 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.337 (3) Å	Cell parameters from 1020 reflections
b = 10.767 (5) Å	θ = 2.6–23.8°
c = 10.967 (5) Å	µ = 1.39 mm^−1
α = 93.602 (7)°	T = 298 K
β = 104.926 (7)°	Prism, blue
γ = 104.640 (7)°	0.26 × 0.22 × 0.19 mm
V = 802.3 (6) Å^3

Data collection

Bruker SMART CCD area-detector diffractometer	2597 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.017
Graphite monochromator	θmax = 25.5°, θmin = 1.9°
φ and ω scans	h = −8→8
4286 measured reflections	k = −12→13
2901 independent reflections	l = −13→13

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.103	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0593P)^2 + 0.3956P] where P = (Fo^2 + 2Fc^2)/3
2901 reflections	(Δ/σ)max = 0.001
225 parameters	Δρmax = 0.34 e Å^−3
3 restraints	Δρmin = −0.35 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	0.11952 (5)	0.25750 (3)	0.69299 (3)	0.02962 (15)
N1	0.2400 (4)	0.4486 (2)	0.7438 (2)	0.0291 (5)
N2	0.1384 (3)	0.3075 (2)	0.5238 (2)	0.0287 (5)
O1	0.0944 (3)	0.2205 (2)	0.8598 (2)	0.0384 (5)
O1W	0.4437 (4)	0.2295 (3)	0.7517 (3)	0.0581 (7)
O2	0.2259 (4)	0.0548 (2)	0.8624 (3)	0.0590 (7)
O3	−0.0730 (3)	0.09078 (18)	0.6129 (2)	0.0339 (5)
O4	−0.2717 (3)	0.21585 (19)	0.6182 (2)	0.0410 (5)
C1	0.1170 (5)	0.1119 (3)	0.8932 (3)	0.0358 (7)
C2	−0.0062 (5)	0.0538 (3)	0.9756 (3)	0.0350 (7)
H2B	−0.0954	0.0951	0.9932	0.042*
C3	−0.4098 (4)	−0.0037 (3)	0.5204 (3)	0.0356 (7)
H3A	−0.3854	−0.0832	0.5059	0.043*
C4	−0.2409 (4)	0.1102 (3)	0.5893 (3)	0.0319 (6)
C5	0.2909 (5)	0.5132 (3)	0.8608 (3)	0.0363 (7)
H5A	0.2722	0.4668	0.9274	0.044*
C6	0.3700 (5)	0.6453 (3)	0.8870 (3)	0.0381 (7)
H6A	0.4042	0.6866	0.9701	0.046*
C7	0.3986 (4)	0.7170 (3)	0.7894 (3)	0.0343 (7)
C8	0.3465 (4)	0.6489 (3)	0.6678 (3)	0.0313 (6)
H8A	0.3640	0.6931	0.5997	0.038*
C9	0.2690 (4)	0.5161 (3)	0.6476 (3)	0.0269 (6)
C10	0.2106 (4)	0.4348 (3)	0.5215 (3)	0.0271 (6)
C11	0.2288 (4)	0.4834 (3)	0.4102 (3)	0.0321 (6)
H11A	0.2788	0.5720	0.4113	0.039*
C12	0.1724 (4)	0.3999 (3)	0.2966 (3)	0.0352 (7)
C13	0.0987 (5)	0.2692 (3)	0.3008 (3)	0.0385 (7)
H13A	0.0594	0.2103	0.2269	0.046*
C14	0.0835 (4)	0.2261 (3)	0.4146 (3)	0.0342 (7)
H14A	0.0336	0.1379	0.4158	0.041*
C15	0.4810 (6)	0.8615 (3)	0.8116 (4)	0.0524 (9)
H15A	0.5082	0.8923	0.9003	0.079*
H15B	0.3874	0.9001	0.7619	0.079*
H15C	0.6002	0.8848	0.7869	0.079*
C16	0.1901 (5)	0.4510 (4)	0.1751 (3)	0.0487 (9)
H16A	0.2442	0.5434	0.1915	0.073*
H16B	0.0626	0.4294	0.1145	0.073*
H16C	0.2750	0.4128	0.1414	0.073*
HW1A	0.525 (5)	0.212 (4)	0.716 (4)	0.068 (13)*
HW1B	0.411 (7)	0.167 (3)	0.791 (4)	0.092 (17)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cu1	0.0362 (2)	0.0242 (2)	0.0265 (2)	0.00238 (15)	0.01045 (15)	0.00776 (14)
N1	0.0333 (13)	0.0273 (12)	0.0258 (12)	0.0043 (10)	0.0102 (10)	0.0053 (10)
N2	0.0329 (13)	0.0258 (12)	0.0269 (12)	0.0061 (10)	0.0096 (10)	0.0049 (10)
O1	0.0547 (14)	0.0305 (11)	0.0328 (11)	0.0077 (10)	0.0193 (10)	0.0121 (9)
O1W	0.0596 (17)	0.0597 (16)	0.076 (2)	0.0279 (14)	0.0394 (15)	0.0290 (15)
O2	0.0721 (18)	0.0612 (16)	0.0725 (18)	0.0331 (15)	0.0489 (15)	0.0391 (14)
O3	0.0316 (11)	0.0251 (10)	0.0428 (12)	0.0037 (8)	0.0106 (9)	0.0054 (9)
O4	0.0397 (12)	0.0266 (11)	0.0546 (14)	0.0055 (9)	0.0134 (11)	0.0044 (10)
C1	0.0441 (18)	0.0337 (16)	0.0296 (16)	0.0059 (14)	0.0142 (14)	0.0100 (12)
C2	0.0417 (17)	0.0327 (15)	0.0302 (16)	0.0049 (13)	0.0135 (13)	0.0087 (12)
C3	0.0367 (15)	0.0267 (14)	0.0403 (17)	0.0038 (13)	0.0104 (14)	0.0056 (13)
C4	0.0347 (16)	0.0265 (14)	0.0311 (16)	0.0012 (12)	0.0091 (13)	0.0101 (12)
C5	0.0449 (18)	0.0409 (17)	0.0237 (15)	0.0107 (14)	0.0115 (13)	0.0060 (13)
C6	0.0447 (18)	0.0373 (17)	0.0299 (16)	0.0096 (14)	0.0101 (14)	−0.0038 (13)
C7	0.0305 (16)	0.0305 (15)	0.0396 (17)	0.0082 (13)	0.0068 (13)	0.0024 (13)
C8	0.0349 (16)	0.0285 (14)	0.0301 (15)	0.0073 (12)	0.0093 (12)	0.0072 (12)
C9	0.0279 (14)	0.0275 (14)	0.0254 (14)	0.0064 (11)	0.0084 (11)	0.0066 (11)
C10	0.0284 (14)	0.0279 (14)	0.0253 (14)	0.0060 (11)	0.0095 (12)	0.0045 (11)
C11	0.0368 (16)	0.0298 (15)	0.0312 (16)	0.0066 (12)	0.0135 (13)	0.0091 (12)
C12	0.0332 (16)	0.0472 (18)	0.0292 (16)	0.0117 (14)	0.0141 (13)	0.0098 (13)
C13	0.0433 (18)	0.0414 (17)	0.0283 (16)	0.0092 (14)	0.0102 (14)	−0.0032 (13)
C14	0.0368 (16)	0.0288 (15)	0.0332 (16)	0.0029 (13)	0.0103 (13)	0.0012 (12)
C15	0.065 (2)	0.0317 (17)	0.051 (2)	0.0074 (17)	0.0084 (18)	−0.0025 (15)
C16	0.050 (2)	0.066 (2)	0.0312 (18)	0.0108 (18)	0.0179 (15)	0.0132 (16)

Geometric parameters (Å, º)

Cu1—O1	1.941 (2)	C5—H5A	0.930
Cu1—O3	1.967 (2)	C6—C7	1.387 (4)
Cu1—N2	1.993 (2)	C6—H6A	0.930
Cu1—N1	2.002 (2)	C7—C8	1.391 (4)
Cu1—O1W	2.400 (3)	C7—C15	1.499 (4)
Cu1—O4	2.684 (3)	C8—C9	1.379 (4)
N1—C5	1.334 (4)	C8—H8A	0.930
N1—C9	1.348 (3)	C9—C10	1.488 (4)
N2—C10	1.343 (4)	C10—C11	1.382 (4)
N2—C14	1.344 (4)	C11—C12	1.392 (4)
O1—C1	1.284 (4)	C11—H11A	0.930
O1W—HW1A	0.842 (10)	C12—C13	1.383 (4)
O1W—HW1B	0.845 (10)	C12—C16	1.497 (4)
O2—C1	1.221 (4)	C13—C14	1.379 (4)
O3—C4	1.265 (4)	C13—H13A	0.930
O4—C4	1.253 (4)	C14—H14A	0.930
C1—C2	1.494 (4)	C15—H15A	0.960
C2—C2^i	1.321 (6)	C15—H15B	0.960
C2—H2B	0.930	C15—H15C	0.960
C3—C3^ii	1.309 (6)	C16—H16A	0.960
C3—C4	1.498 (4)	C16—H16B	0.960
C3—H3A	0.930	C16—H16C	0.960
C5—C6	1.375 (4)
O1—Cu1—O3	90.74 (9)	C6—C5—H5A	118.6
O1—Cu1—O4	87.34 (8)	C5—C6—C7	119.9 (3)
O1—Cu1—N2	175.59 (9)	C5—C6—H6A	120.1
O3—Cu1—N2	91.48 (9)	C7—C6—H6A	120.1
O1—Cu1—N1	95.77 (9)	C6—C7—C8	117.0 (3)
O3—Cu1—N1	160.67 (9)	C6—C7—C15	122.4 (3)
N2—Cu1—N1	80.93 (9)	C8—C7—C15	120.7 (3)
O1—Cu1—O1W	89.45 (10)	C9—C8—C7	120.5 (3)
O3—Cu1—O1W	109.60 (10)	C9—C8—H8A	119.8
N2—Cu1—O1W	93.40 (10)	C7—C8—H8A	119.8
N1—Cu1—O1W	88.70 (10)	N1—C9—C8	121.5 (3)
O1W—Cu1—O4	163.87 (9)	N1—C9—C10	114.2 (2)
O3—Cu1—O4	54.68 (8)	C8—C9—C10	124.3 (2)
O4—Cu1—N1	107.37 (10)	N2—C10—C11	121.7 (3)
O4—Cu1—N2	90.84 (8)	N2—C10—C9	114.3 (2)
C5—N1—C9	118.4 (2)	C11—C10—C9	124.0 (2)
C5—N1—Cu1	126.5 (2)	C10—C11—C12	120.1 (3)
C9—N1—Cu1	115.04 (18)	C10—C11—H11A	119.9
C10—N2—C14	118.7 (2)	C12—C11—H11A	119.9
C10—N2—Cu1	115.50 (18)	C13—C12—C11	117.4 (3)
C14—N2—Cu1	125.8 (2)	C13—C12—C16	121.8 (3)
C1—O1—Cu1	117.47 (19)	C11—C12—C16	120.8 (3)
Cu1—O1W—HW1A	138 (3)	C14—C13—C12	120.0 (3)
Cu1—O1W—HW1B	93 (3)	C14—C13—H13A	120.0
HW1A—O1W—HW1B	106 (2)	C12—C13—H13A	120.0
C4—O3—Cu1	106.78 (18)	N2—C14—C13	122.1 (3)
O2—C1—O1	125.9 (3)	N2—C14—H14A	118.9
O2—C1—C2	119.5 (3)	C13—C14—H14A	118.9
O1—C1—C2	114.6 (3)	C7—C15—H15A	109.5
C2^i—C2—C1	122.7 (4)	C7—C15—H15B	109.5
C2^i—C2—H2B	118.6	H15A—C15—H15B	109.5
C1—C2—H2B	118.6	C7—C15—H15C	109.5
C3^ii—C3—C4	122.9 (4)	H15A—C15—H15C	109.5
C3^ii—C3—H3A	118.6	H15B—C15—H15C	109.5
C4—C3—H3A	118.6	C12—C16—H16A	109.5
O4—C4—O3	124.6 (3)	C12—C16—H16B	109.5
O4—C4—C3	119.8 (3)	H16A—C16—H16B	109.5
O3—C4—C3	115.6 (3)	C12—C16—H16C	109.5
N1—C5—C6	122.7 (3)	H16A—C16—H16C	109.5
N1—C5—H5A	118.6	H16B—C16—H16C	109.5
O1—Cu1—N1—C5	4.2 (3)	Cu1—N1—C5—C6	−178.8 (2)
O3—Cu1—N1—C5	113.3 (3)	N1—C5—C6—C7	0.3 (5)
N2—Cu1—N1—C5	−178.7 (3)	C5—C6—C7—C8	−0.8 (5)
O1W—Cu1—N1—C5	−85.1 (3)	C5—C6—C7—C15	179.0 (3)
O1—Cu1—N1—C9	−175.2 (2)	C6—C7—C8—C9	0.4 (4)
O3—Cu1—N1—C9	−66.1 (3)	C15—C7—C8—C9	−179.4 (3)
N2—Cu1—N1—C9	1.9 (2)	C5—N1—C9—C8	−1.0 (4)
O1W—Cu1—N1—C9	95.5 (2)	Cu1—N1—C9—C8	178.5 (2)
O3—Cu1—N2—C10	160.3 (2)	C5—N1—C9—C10	179.0 (2)
N1—Cu1—N2—C10	−1.9 (2)	Cu1—N1—C9—C10	−1.6 (3)
O1W—Cu1—N2—C10	−90.0 (2)	C7—C8—C9—N1	0.5 (4)
O3—Cu1—N2—C14	−18.8 (2)	C7—C8—C9—C10	−179.5 (3)
N1—Cu1—N2—C14	179.1 (3)	C14—N2—C10—C11	0.2 (4)
O1W—Cu1—N2—C14	90.9 (2)	Cu1—N2—C10—C11	−178.9 (2)
O3—Cu1—O1—C1	52.5 (2)	C14—N2—C10—C9	−179.3 (2)
N1—Cu1—O1—C1	−145.7 (2)	Cu1—N2—C10—C9	1.6 (3)
O1W—Cu1—O1—C1	−57.0 (2)	N1—C9—C10—N2	0.0 (4)
O1—Cu1—O3—C4	87.50 (19)	C8—C9—C10—N2	180.0 (3)
N2—Cu1—O3—C4	−88.69 (19)	N1—C9—C10—C11	−179.5 (3)
N1—Cu1—O3—C4	−22.4 (4)	C8—C9—C10—C11	0.5 (5)
O1W—Cu1—O3—C4	177.18 (18)	N2—C10—C11—C12	−0.2 (4)
Cu1—O1—C1—O2	32.4 (5)	C9—C10—C11—C12	179.2 (3)
Cu1—O1—C1—C2	−146.7 (2)	C10—C11—C12—C13	0.1 (4)
O2—C1—C2—C2^i	4.6 (6)	C10—C11—C12—C16	179.7 (3)
O1—C1—C2—C2^i	−176.2 (4)	C11—C12—C13—C14	0.0 (5)
Cu1—O3—C4—O4	−2.7 (3)	C16—C12—C13—C14	−179.5 (3)
Cu1—O3—C4—C3	176.5 (2)	C10—N2—C14—C13	−0.1 (4)
C3^ii—C3—C4—O4	5.2 (6)	Cu1—N2—C14—C13	178.9 (2)
C3^ii—C3—C4—O3	−174.0 (4)	C12—C13—C14—N2	0.0 (5)
C9—N1—C5—C6	0.6 (5)

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—HW1A···O4	0.84 (4)	2.04 (4)	2.869 (4)	166 (4)
O1W—HW1B···O2	0.84 (4)	1.94 (4)	2.708 (4)	152 (5)