Coordination polymer chains built from CuII and adipate ions linked by hydrogen bonds to form a three-dimensional framework structure

Setifi, Z.; Boutebdja, M.; Setifi, F.; Merazig, H.; Glidewell, C.

doi:10.1107/S205322961401359X

Coordination polymer chains built from Cu^II and adipate ions linked by hydrogen bonds to form a three-dimensional framework structure

Z. Setifi, M. Boutebdja, F. Setifi, H. Merazig and C. Glidewell

In the title compound, catena-poly[bis[(2,2′-bipyridine-κ²N,N′)(1,1,3,3-tetracyano-2-ethoxypropenido-κN)copper(II)]-μ₄-hexanedioato-κ⁶O¹,O^1′:O¹:O⁶,O^6′:O⁶], [Cu₂(C₉H₅N₄O)₂(C₆H₈O₄)(C₁₀H₈N₂)₂]_n, the adipate (hexanedioate) dianion lies across a centre of inversion in the space group P $\overline{1}$ . The Cu^II centre adopts a distorted form of axially elongated (4+2) coordination, and the Cu^II and adipate components form a one-dimensional coordination polymer from which the 2,2′-bipyridine and 1,1,3,3-tetracyano-2-ethoxypropenide components are pendent, and where each adipate dianion is bonded to four different Cu^II centres. The coordination polymer chains are linked into a three-dimensional framework structure by a combination of C—H

N and C—H

O hydrogen bonds, augmented by a π–π stacking interaction.

Keywords: crystal structure; one-dimensional coordination polymer; copper(II) complex; adipate; π–π stacking interactions; 2,2′-bipyridine; polynitrile anions; 1,1,3,3-tetracyano-2-ethoxypropenide.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S205322961401359X/yf3065sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S205322961401359X/yf3065Isup2.hkl Contains datablock I

CCDC reference: 1007824

Computing details top

Data collection: CrysAlis PRO (Agilent, 2013); cell refinement: CrysAlis PRO (Agilent, 2013); data reduction: CrysAlis PRO (Agilent, 2013); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2014); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2014) and PLATON (Spek, 2009).

catena-poly[bis[(2,2'-bipyridine-κ²N,N')(1,1,3,3-tetracyano-2-ethoxypropenido-κN)copper(II)]-µ₄-hexane-1,6-dioato-κ⁶O¹,O^1':O¹:O⁶,O^6':O⁶] top

Crystal data top

[Cu₂(C₉H₅N₄O)₂(C₆H₈O₄)(C₁₀H₈N₂)₂]	Z = 2
M_r = 476.97	F(000) = 488
Triclinic, P1	D_x = 1.472 Mg m⁻³
a = 8.8825 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.5610 (4) Å	Cell parameters from 26499 reflections
c = 12.2541 (5) Å	θ = 3.0–31.7°
α = 71.724 (3)°	µ = 1.05 mm⁻¹
β = 80.582 (4)°	T = 150 K
γ = 84.974 (3)°	Plate, blue
V = 1076.03 (7) Å³	0.20 × 0.15 × 0.10 mm

Data collection top

Agilent Xcalibur Sapphire2 diffractometer	6143 independent reflections
Radiation source: Enhance (Mo) X-ray Source	4850 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.021
Detector resolution: 9.091 pixels mm^-1	θ_max = 30.0°, θ_min = 3.0°
ω scans	h = −12→12
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	k = −14→14
T_min = 0.771, T_max = 0.929	l = −17→13
10761 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.078	H-atom parameters constrained
S = 0.96	w = 1/[σ²(F_o²) + (0.0442P)²] where P = (F_o² + 2F_c²)/3
6143 reflections	(Δ/σ)_max = 0.001
290 parameters	Δρ_max = 0.46 e Å⁻³
0 restraints	Δρ_min = −0.24 e Å⁻³

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Cu1	0.67620 (2)	0.02804 (2)	0.43636 (2)	0.01549 (6)
N11	0.83199 (14)	−0.07966 (13)	0.36463 (11)	0.0171 (3)
C12	0.92158 (17)	−0.16286 (16)	0.43799 (15)	0.0183 (3)
C13	1.02475 (19)	−0.25364 (18)	0.40281 (17)	0.0271 (4)
H13	1.0856	−0.3127	0.4556	0.033*
C14	1.0379 (2)	−0.2570 (2)	0.28951 (18)	0.0314 (4)
H14	1.1082	−0.3183	0.2637	0.038*
C15	0.9480 (2)	−0.17036 (19)	0.21448 (17)	0.0284 (4)
H15	0.9563	−0.1704	0.1362	0.034*
C16	0.84563 (19)	−0.08370 (17)	0.25537 (15)	0.0223 (3)
H16	0.7827	−0.0249	0.2041	0.027*
N21	0.78358 (15)	−0.05943 (13)	0.57302 (11)	0.0168 (3)
C22	0.89765 (17)	−0.14788 (15)	0.55611 (14)	0.0176 (3)
C23	0.98343 (19)	−0.21505 (18)	0.64309 (16)	0.0254 (4)
H23	1.0631	−0.2770	0.6300	0.030*
C24	0.9517 (2)	−0.19086 (19)	0.74950 (16)	0.0275 (4)
H24	1.0092	−0.2361	0.8102	0.033*
C25	0.83545 (19)	−0.10028 (17)	0.76607 (15)	0.0238 (4)
H25	0.8122	−0.0822	0.8383	0.029*
C26	0.75326 (19)	−0.03618 (16)	0.67625 (14)	0.0205 (3)
H26	0.6731	0.0261	0.6879	0.025*
C31	0.45825 (19)	0.31347 (16)	0.14602 (14)	0.0196 (3)
C32	0.44649 (18)	0.29425 (16)	0.03834 (14)	0.0200 (3)
C33	0.5597 (2)	0.22925 (18)	−0.01953 (14)	0.0239 (4)
C311	0.3582 (2)	0.40499 (17)	0.18925 (15)	0.0235 (3)
N311	0.2789 (2)	0.47836 (18)	0.22640 (16)	0.0390 (4)
C312	0.54965 (18)	0.22554 (16)	0.22276 (14)	0.0196 (3)
N312	0.62068 (17)	0.15319 (14)	0.28773 (12)	0.0232 (3)
O321	0.31363 (13)	0.34181 (12)	0.00000 (10)	0.0251 (3)
C321	0.3025 (2)	0.38306 (19)	−0.12369 (15)	0.0292 (4)
H32A	0.2851	0.3052	−0.1481	0.035*
H32B	0.3977	0.4247	−0.1697	0.035*
C322	0.1697 (3)	0.4819 (2)	−0.14135 (19)	0.0453 (6)
H32C	0.1895	0.5591	−0.1184	0.068*
H32D	0.0769	0.4399	−0.0938	0.068*
H32E	0.1560	0.5113	−0.2234	0.068*
C331	0.5301 (2)	0.1641 (2)	−0.09915 (16)	0.0318 (4)
N331	0.5069 (2)	0.1076 (2)	−0.16029 (17)	0.0473 (5)
C332	0.7124 (2)	0.2165 (2)	0.00508 (15)	0.0290 (4)
N332	0.83659 (19)	0.2075 (2)	0.02288 (14)	0.0397 (4)
O41	0.51673 (12)	0.11565 (10)	0.51947 (9)	0.0163 (2)
O42	0.68662 (13)	0.27034 (12)	0.47807 (12)	0.0268 (3)
C41	0.55653 (18)	0.23265 (15)	0.51653 (13)	0.0166 (3)
C42	0.43386 (19)	0.31663 (16)	0.56424 (15)	0.0221 (3)
H42A	0.3959	0.2665	0.6457	0.027*
H42B	0.3474	0.3312	0.5193	0.027*
C43	0.4852 (2)	0.45202 (15)	0.56094 (14)	0.0222 (3)
H43A	0.4056	0.4922	0.6080	0.027*
H43B	0.5798	0.4387	0.5968	0.027*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.01577 (10)	0.01501 (10)	0.01572 (10)	0.00385 (7)	−0.00233 (7)	−0.00586 (7)
N11	0.0151 (6)	0.0169 (6)	0.0192 (7)	−0.0001 (5)	−0.0002 (5)	−0.0067 (5)
C12	0.0126 (7)	0.0164 (7)	0.0265 (8)	−0.0006 (6)	−0.0022 (6)	−0.0078 (7)
C13	0.0189 (8)	0.0256 (9)	0.0410 (11)	0.0061 (7)	−0.0062 (7)	−0.0170 (8)
C14	0.0207 (8)	0.0333 (10)	0.0471 (12)	0.0045 (7)	0.0000 (8)	−0.0261 (9)
C15	0.0241 (9)	0.0357 (10)	0.0309 (10)	−0.0021 (8)	0.0026 (7)	−0.0209 (8)
C16	0.0216 (8)	0.0247 (8)	0.0218 (8)	−0.0003 (7)	−0.0004 (6)	−0.0104 (7)
N21	0.0160 (6)	0.0163 (6)	0.0190 (7)	0.0004 (5)	−0.0028 (5)	−0.0067 (5)
C22	0.0132 (7)	0.0156 (7)	0.0232 (8)	−0.0002 (6)	−0.0027 (6)	−0.0048 (6)
C23	0.0186 (8)	0.0243 (9)	0.0295 (9)	0.0041 (7)	−0.0057 (7)	−0.0029 (7)
C24	0.0226 (8)	0.0298 (9)	0.0256 (9)	−0.0011 (7)	−0.0094 (7)	0.0008 (8)
C25	0.0257 (8)	0.0261 (9)	0.0185 (8)	−0.0059 (7)	−0.0031 (7)	−0.0040 (7)
C26	0.0208 (8)	0.0200 (8)	0.0208 (8)	−0.0007 (6)	−0.0023 (6)	−0.0068 (7)
C31	0.0214 (8)	0.0190 (8)	0.0171 (8)	0.0017 (6)	−0.0036 (6)	−0.0039 (6)
C32	0.0206 (8)	0.0192 (8)	0.0174 (8)	−0.0014 (6)	−0.0028 (6)	−0.0014 (6)
C33	0.0268 (9)	0.0264 (9)	0.0182 (8)	0.0038 (7)	−0.0051 (7)	−0.0069 (7)
C311	0.0259 (8)	0.0225 (8)	0.0215 (8)	0.0004 (7)	−0.0060 (7)	−0.0047 (7)
N311	0.0415 (10)	0.0365 (10)	0.0425 (10)	0.0100 (8)	−0.0056 (8)	−0.0202 (8)
C312	0.0212 (8)	0.0207 (8)	0.0163 (8)	−0.0007 (6)	0.0006 (6)	−0.0066 (6)
N312	0.0286 (7)	0.0232 (7)	0.0167 (7)	0.0058 (6)	−0.0030 (6)	−0.0063 (6)
O321	0.0229 (6)	0.0320 (7)	0.0188 (6)	0.0045 (5)	−0.0071 (5)	−0.0049 (5)
C321	0.0343 (10)	0.0329 (10)	0.0206 (9)	0.0028 (8)	−0.0128 (8)	−0.0052 (8)
C322	0.0541 (14)	0.0448 (13)	0.0393 (12)	0.0192 (11)	−0.0265 (11)	−0.0118 (10)
C331	0.0384 (10)	0.0337 (10)	0.0241 (9)	0.0124 (8)	−0.0079 (8)	−0.0117 (8)
N331	0.0595 (12)	0.0515 (12)	0.0417 (11)	0.0196 (10)	−0.0180 (9)	−0.0301 (10)
C332	0.0323 (10)	0.0353 (10)	0.0166 (8)	0.0063 (8)	0.0008 (7)	−0.0083 (8)
N332	0.0286 (9)	0.0629 (12)	0.0246 (8)	0.0078 (8)	−0.0005 (7)	−0.0134 (8)
O41	0.0177 (5)	0.0123 (5)	0.0201 (6)	0.0013 (4)	−0.0024 (4)	−0.0070 (4)
O42	0.0172 (6)	0.0208 (6)	0.0442 (8)	−0.0005 (5)	−0.0011 (5)	−0.0140 (6)
C41	0.0191 (7)	0.0135 (7)	0.0183 (8)	0.0022 (6)	−0.0048 (6)	−0.0061 (6)
C42	0.0236 (8)	0.0134 (7)	0.0271 (9)	0.0003 (6)	0.0045 (7)	−0.0074 (7)
C43	0.0339 (9)	0.0132 (7)	0.0207 (8)	−0.0003 (7)	−0.0006 (7)	−0.0086 (6)

Geometric parameters (Å, º) top

Cu1—N11	1.9835 (13)	C32—C33	1.391 (2)
Cu1—N21	1.9914 (13)	C31—C311	1.422 (2)
Cu1—N312	1.9943 (14)	C31—C312	1.406 (2)
Cu1—O41	1.9466 (11)	O41—C41	1.3029 (18)
Cu1—O42	2.7741 (14)	C311—N311	1.151 (2)
Cu1—O41ⁱ	2.2737 (11)	C312—N312	1.146 (2)
N11—C16	1.338 (2)	C32—O321	1.3400 (19)
N11—C12	1.353 (2)	C33—C331	1.425 (2)
C12—C13	1.386 (2)	C33—C332	1.423 (3)
C12—C22	1.484 (2)	O321—C321	1.458 (2)
C13—C14	1.386 (3)	C321—C322	1.501 (3)
C13—H13	0.9500	C321—H32A	0.9900
C14—C15	1.381 (3)	C321—H32B	0.9900
C14—H14	0.9500	C322—H32C	0.9800
C15—C16	1.381 (2)	C322—H32D	0.9800
C15—H15	0.9500	C322—H32E	0.9800
C16—H16	0.9500	C331—N331	1.146 (2)
N21—C26	1.343 (2)	C332—N332	1.149 (2)
N21—C22	1.3524 (19)	O41—Cu1ⁱ	2.2737 (11)
C22—C23	1.384 (2)	O42—C41	1.2250 (19)
C23—C24	1.386 (3)	C41—C42	1.504 (2)
C23—H23	0.9500	C42—C43	1.525 (2)
C24—C25	1.379 (2)	C42—H42A	0.9900
C24—H24	0.9500	C42—H42B	0.9900
C25—C26	1.383 (2)	C43—C43ⁱⁱ	1.515 (3)
C25—H25	0.9500	C43—H43A	0.9900
C26—H26	0.9500	C43—H43B	0.9900
C31—C32	1.418 (2)

N11—Cu1—N21	81.40 (5)	N21—C26—C25	121.84 (15)
N11—Cu1—O41	173.79 (5)	N21—C26—H26	119.1
N21—Cu1—O41	95.13 (5)	C25—C26—H26	119.1
N11—Cu1—N312	96.26 (6)	C312—C31—C32	120.45 (15)
N21—Cu1—N312	162.55 (6)	C312—C31—C311	117.27 (14)
O41—Cu1—N312	88.58 (5)	C32—C31—C311	121.27 (14)
O41—Cu1—O42	52.20 (4)	O321—C32—C33	123.67 (15)
O42—Cu1—N11	132.48 (5)	O321—C32—C31	113.01 (14)
O42—Cu1—N21	89.09 (5)	C33—C32—C31	123.30 (15)
O42—Cu1—N312	79.72 (5)	C32—C33—C332	120.54 (15)
O41—Cu1—O41ⁱ	78.46 (4)	C32—C33—C331	123.30 (16)
O42—Cu1—O41ⁱ	130.61 (4)	C332—C33—C331	116.01 (16)
N11—Cu1—O41ⁱ	96.88 (5)	N311—C311—C31	178.43 (19)
N21—Cu1—O41ⁱ	98.30 (5)	N312—C312—C31	178.08 (18)
N312—Cu1—O41ⁱ	99.15 (5)	C312—N312—Cu1	160.19 (14)
C16—N11—C12	119.14 (14)	C32—O321—C321	120.66 (13)
C16—N11—Cu1	125.59 (11)	O321—C321—C322	106.34 (16)
C12—N11—Cu1	115.03 (11)	O321—C321—H32A	110.5
N11—C12—C13	121.30 (16)	C322—C321—H32A	110.5
N11—C12—C22	114.21 (13)	O321—C321—H32B	110.5
C13—C12—C22	124.48 (15)	C322—C321—H32B	110.5
C14—C13—C12	119.07 (17)	H32A—C321—H32B	108.7
C14—C13—H13	120.5	C321—C322—H32C	109.5
C12—C13—H13	120.5	C321—C322—H32D	109.5
C15—C14—C13	119.37 (16)	H32C—C322—H32D	109.5
C15—C14—H14	120.3	C321—C322—H32E	109.5
C13—C14—H14	120.3	H32C—C322—H32E	109.5
C14—C15—C16	118.76 (17)	H32D—C322—H32E	109.5
C14—C15—H15	120.6	N331—C331—C33	177.6 (2)
C16—C15—H15	120.6	N332—C332—C33	178.7 (2)
N11—C16—C15	122.34 (16)	C41—O41—Cu1	111.58 (10)
N11—C16—H16	118.8	C41—O41—Cu1ⁱ	146.30 (10)
C15—C16—H16	118.8	Cu1—O41—Cu1ⁱ	101.54 (4)
C26—N21—C22	119.27 (14)	O42—C41—O41	121.48 (15)
C26—N21—Cu1	125.75 (11)	O42—C41—C42	122.62 (14)
C22—N21—Cu1	114.97 (11)	O41—C41—C42	115.90 (13)
N21—C22—C23	121.33 (15)	C41—C42—C43	114.41 (14)
N21—C22—C12	114.08 (14)	C41—C42—H42A	108.7
C23—C22—C12	124.59 (14)	C43—C42—H42A	108.7
C22—C23—C24	119.22 (16)	C41—C42—H42B	108.7
C22—C23—H23	120.4	C43—C42—H42B	108.7
C24—C23—H23	120.4	H42A—C42—H42B	107.6
C25—C24—C23	119.17 (16)	C43ⁱⁱ—C43—C42	113.11 (17)
C25—C24—H24	120.4	C43ⁱⁱ—C43—H43A	109.0
C23—C24—H24	120.4	C42—C43—H43A	109.0
C24—C25—C26	119.18 (16)	C43ⁱⁱ—C43—H43B	109.0
C24—C25—H25	120.4	C42—C43—H43B	109.0
C26—C25—H25	120.4	H43A—C43—H43B	107.8

C16—N11—C12—C13	−1.3 (2)	C23—C24—C25—C26	0.2 (3)
Cu1—N11—C12—C13	173.42 (13)	C22—N21—C26—C25	0.0 (2)
C16—N11—C12—C22	179.19 (14)	Cu1—N21—C26—C25	−179.01 (12)
Cu1—N11—C12—C22	−6.14 (17)	C24—C25—C26—N21	−0.1 (3)
N11—C12—C13—C14	1.3 (3)	C312—C31—C32—O321	152.09 (15)
C22—C12—C13—C14	−179.24 (16)	C311—C31—C32—O321	−16.1 (2)
C12—C13—C14—C15	−0.2 (3)	C312—C31—C32—C33	−26.2 (3)
C13—C14—C15—C16	−0.8 (3)	O321—C32—C33—C332	161.28 (16)
C12—N11—C16—C15	0.2 (2)	O321—C32—C33—C331	−23.3 (3)
Cu1—N11—C16—C15	−173.86 (13)	C31—C32—C33—C331	154.77 (18)
C14—C15—C16—N11	0.8 (3)	C31—C32—C33—C332	−20.6 (3)
C26—N21—C22—C23	0.1 (2)	C33—C32—C31—C311	165.66 (17)
Cu1—N21—C22—C23	179.22 (12)	C33—C32—O321—C321	−27.7 (2)
C26—N21—C22—C12	−178.94 (14)	C31—C32—O321—C321	154.06 (15)
Cu1—N21—C22—C12	0.14 (17)	C32—O321—C321—C322	−155.75 (16)
N11—C12—C22—N21	3.9 (2)	Cu1—O41—C41—O42	−8.53 (19)
C13—C12—C22—N21	−175.61 (15)	Cu1ⁱ—O41—C41—O42	−177.28 (12)
N11—C12—C22—C23	−175.12 (15)	Cu1—O41—C41—C42	172.13 (11)
C13—C12—C22—C23	5.3 (3)	Cu1ⁱ—O41—C41—C42	3.4 (3)
N21—C22—C23—C24	−0.1 (3)	O42—C41—C42—C43	−0.2 (2)
C12—C22—C23—C24	178.90 (16)	O41—C41—C42—C43	179.18 (14)
C22—C23—C24—C25	−0.1 (3)	C41—C42—C43—C43ⁱⁱ	70.2 (2)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13···O42ⁱⁱⁱ	0.95	2.42	3.118 (2)	130
C15—H15···N332^iv	0.95	2.55	3.322 (3)	138
C23—H23···O42ⁱⁱⁱ	0.95	2.39	3.155 (2)	138
C26—H26···N331^v	0.95	2.50	3.316 (3)	144

Symmetry codes: (iii) −x+2, −y, −z+1; (iv) −x+2, −y, −z; (v) x, y, z+1.

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