Literature DB >> 21577774

Poly[(μ(3)-5-bromo-nicotinato)(5-bromo-nicotinato)copper(II)].

Jun Yang1, Hong-Ji Chen.   

Abstract

The title coordination polymer, [Cu(C(6)H(3)BrNO(2))(2)](n), is composed of two structurally similar two-dimensional coordination polymers (twin layers). Both of them have the same chemical composition but they display different bond lengths and angles. In each layer, two N atoms and four carboxyl-ate O atoms from the bridging 5-bromo-nicotinate ligands and four carboxyl-ate O atoms from the terminal 5-bromo-nicotinate ligands bind to two Cu(II) atoms to form a dinuclear paddle-wheel-like pattern. Adjacent paddle wheels are further linked by bridging 5-bromo-nicotinate groups to generate a two-dimensional coordination polymer; neighboring twin-like layers are finally stacked through π-π stacking interactions between adjacent pyridine rings [perpendicular distance of 3.626 (2) Å] in a 'sandwich' manner, thus generating a three-dimensional supra-molecular structure.

Entities:  

Year:  2009        PMID: 21577774      PMCID: PMC2970337          DOI: 10.1107/S1600536809038331

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN: 1600-5368


Related literature

For related literature on paddle-wheel secondary building units, see: Chen et al. (2006 ▶); Xue et al. (2007 ▶); Striegler & Dittel (2003 ▶); Ma & Moulton (2007 ▶); Banerjee et al. (2008 ▶); Saravanakumar et al. (2004 ▶). For similar structures, see: Yakovenko et al. (2009 ▶); Xue et al. (2007 ▶). For τ distortions of coordination polyhedra, see: Addison & Rao (1984 ▶).

Experimental

Crystal data

[Cu(C6H3BrNO2)2] M = 465.55 Monoclinic, a = 21.542 (4) Å b = 11.746 (2) Å c = 12.271 (2) Å β = 104.31 (3)° V = 3008.6 (9) Å3 Z = 8 Mo Kα radiation μ = 6.78 mm−1 T = 173 K 0.33 × 0.31 × 0.23 mm

Data collection

Bruker SMART CCD area-detector diffractometer Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ▶) T min = 0.213, T max = 0.305 15126 measured reflections 6502 independent reflections 4904 reflections with I > 2σ(I) R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.034 wR(F 2) = 0.085 S = 1.03 6502 reflections 379 parameters H-atom parameters constrained Δρmax = 1.40 e Å−3 Δρmin = −1.34 e Å−3 Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT (Bruker, 1998 ▶); data reduction: SAINT (Bruker, 1998 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg, 2005 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶). Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809038331/bg2298sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536809038331/bg2298Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
[Cu(C6H3BrNO2)2]Z = 8
Mr = 465.55F(000) = 1784
Monoclinic, P21/cDx = 2.056 Mg m3
Hall symbol: -P 2ybcMo Kα radiation, λ = 0.71073 Å
a = 21.542 (4) Åθ = 2.4–27.0°
b = 11.746 (2) ŵ = 6.78 mm1
c = 12.271 (2) ÅT = 173 K
β = 104.31 (3)°Block, blue
V = 3008.6 (9) Å30.33 × 0.31 × 0.23 mm
Bruker SMART CCD area-detector diffractometer6502 independent reflections
Radiation source: fine-focus sealed tube4904 reflections with I > 2σ(I)
graphiteRint = 0.031
φ and ω scansθmax = 27.0°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)h = −27→15
Tmin = 0.213, Tmax = 0.305k = −12→15
15126 measured reflectionsl = −15→15
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.034Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.085H-atom parameters constrained
S = 1.02w = 1/[σ2(Fo2) + (0.0329P)2 + 6.737P] where P = (Fo2 + 2Fc2)/3
6502 reflections(Δ/σ)max = 0.002
379 parametersΔρmax = 1.40 e Å3
0 restraintsΔρmin = −1.33 e Å3
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.
xyzUiso*/Ueq
Br10.36048 (3)1.10765 (4)0.45763 (4)0.04098 (14)
Br20.22167 (2)0.26934 (6)0.04959 (4)0.04929 (17)
Br30.65085 (2)0.30249 (5)−0.19347 (4)0.04179 (15)
Br41.13503 (3)0.60918 (5)0.58445 (4)0.05030 (18)
Cu10.48131 (2)0.52244 (4)0.59219 (4)0.01204 (10)
Cu21.02261 (2)0.48099 (4)0.10871 (4)0.01222 (10)
N10.46040 (15)0.5444 (3)0.7534 (3)0.0155 (7)
N20.20763 (17)0.4113 (4)0.3472 (3)0.0318 (9)
N31.04924 (15)0.4524 (3)0.2885 (3)0.0158 (7)
N40.76951 (19)0.2695 (4)0.1228 (3)0.0389 (10)
O10.39446 (13)0.4902 (3)0.5031 (2)0.0261 (7)
O20.57262 (12)0.5555 (3)0.6502 (2)0.0223 (6)
O30.49764 (14)0.3579 (2)0.6129 (2)0.0223 (6)
O40.46875 (13)0.6827 (2)0.5418 (2)0.0207 (6)
O51.04325 (13)0.3262 (2)0.0652 (2)0.0179 (6)
O60.99585 (14)0.6387 (2)0.1185 (2)0.0247 (7)
O70.93424 (13)0.4281 (3)0.0966 (2)0.0231 (6)
O81.10483 (13)0.5363 (2)0.0872 (2)0.0239 (7)
C10.48052 (18)0.7079 (3)0.4500 (3)0.0157 (8)
C20.46378 (17)0.8249 (3)0.4044 (3)0.0128 (7)
C30.42926 (18)0.9003 (3)0.4536 (3)0.0176 (8)
H3B0.41910.88210.52340.080*
C40.41056 (19)1.0027 (3)0.4004 (3)0.0205 (9)
C50.42629 (19)0.4721 (3)0.7994 (3)0.0198 (8)
H5A0.41440.40510.76570.050*
C60.47896 (17)0.6433 (3)0.8054 (3)0.0153 (8)
H6A0.50270.68960.77250.050*
C70.38534 (18)0.4560 (3)0.4041 (3)0.0169 (8)
C80.31838 (17)0.4236 (3)0.3453 (3)0.0175 (8)
C90.30550 (19)0.3730 (4)0.2396 (4)0.0241 (9)
H9A0.33880.36060.20150.080*
C100.24266 (19)0.3414 (4)0.1909 (3)0.0241 (9)
C110.19555 (19)0.3611 (4)0.2464 (4)0.0249 (9)
H11A0.15250.33810.21150.080*
C120.2679 (2)0.4414 (4)0.3946 (4)0.0260 (9)
H12A0.27690.47720.46720.080*
C130.89075 (18)0.4275 (3)0.0067 (3)0.0176 (8)
C140.82826 (18)0.3749 (3)0.0129 (3)0.0177 (8)
C150.77755 (19)0.3685 (3)−0.0817 (3)0.0208 (9)
H15A0.78030.4012−0.15200.080*
C160.72308 (18)0.3128 (4)−0.0705 (3)0.0226 (9)
C170.7203 (2)0.2648 (4)0.0305 (4)0.0325 (11)
H17A0.68170.22660.03540.080*
C180.8221 (2)0.3253 (4)0.1122 (4)0.0301 (10)
H18A0.85730.33130.17740.080*
C191.02976 (18)0.2986 (3)−0.0370 (3)0.0152 (8)
C201.04662 (17)0.1814 (3)−0.0668 (3)0.0132 (7)
C211.07623 (18)0.1035 (3)0.0149 (3)0.0154 (8)
H21A1.08410.12300.09500.050*
C221.09175 (19)0.5010 (3)0.4790 (3)0.0191 (8)
C231.07778 (18)0.5271 (3)0.3658 (3)0.0182 (8)
H23A1.08920.60070.34280.080*
C241.03400 (17)0.3506 (3)0.3220 (3)0.0151 (8)
H24A1.01140.29880.26260.050*
U11U22U33U12U13U23
Br10.0617 (3)0.0352 (3)0.0350 (3)0.0291 (2)0.0292 (2)0.0086 (2)
Br20.0306 (3)0.0809 (4)0.0360 (3)−0.0217 (3)0.0076 (2)−0.0310 (3)
Br30.0203 (2)0.0719 (4)0.0300 (3)−0.0167 (2)0.00016 (18)−0.0005 (2)
Br40.0942 (5)0.0338 (3)0.0177 (2)−0.0389 (3)0.0040 (2)−0.0080 (2)
Cu10.0157 (2)0.0104 (2)0.0101 (2)−0.00042 (17)0.00348 (17)−0.00025 (17)
Cu20.0160 (2)0.0096 (2)0.0094 (2)−0.00019 (17)0.00013 (17)−0.00022 (17)
N10.0182 (16)0.0147 (18)0.0131 (15)−0.0002 (12)0.0029 (13)−0.0016 (13)
N20.0186 (19)0.050 (3)0.026 (2)0.0006 (17)0.0042 (15)−0.0037 (18)
N30.0203 (17)0.0119 (17)0.0147 (16)−0.0012 (12)0.0031 (13)0.0012 (12)
N40.032 (2)0.060 (3)0.027 (2)−0.011 (2)0.0113 (17)0.008 (2)
O10.0174 (15)0.0376 (19)0.0224 (15)−0.0036 (12)0.0032 (12)−0.0094 (13)
O20.0145 (14)0.0315 (17)0.0205 (15)−0.0023 (12)0.0034 (11)−0.0019 (12)
O30.0369 (17)0.0149 (15)0.0186 (14)0.0039 (12)0.0136 (13)0.0021 (12)
O40.0353 (17)0.0144 (15)0.0163 (14)0.0052 (12)0.0137 (12)0.0061 (11)
O50.0270 (15)0.0137 (14)0.0112 (13)0.0033 (11)0.0016 (11)−0.0041 (11)
O60.0450 (18)0.0119 (15)0.0146 (14)0.0080 (13)0.0023 (13)0.0011 (11)
O70.0167 (14)0.0336 (18)0.0182 (15)−0.0019 (12)0.0032 (11)−0.0022 (13)
O80.0197 (15)0.0284 (18)0.0199 (15)−0.0079 (12)−0.0018 (11)0.0085 (12)
C10.0186 (19)0.012 (2)0.0155 (19)−0.0014 (15)0.0026 (15)0.0005 (15)
C20.0133 (18)0.015 (2)0.0089 (17)−0.0015 (14)0.0002 (13)0.0002 (14)
C30.020 (2)0.017 (2)0.0148 (19)−0.0020 (15)0.0037 (15)0.0015 (16)
C40.026 (2)0.017 (2)0.022 (2)0.0073 (16)0.0133 (17)−0.0017 (16)
C50.027 (2)0.015 (2)0.018 (2)−0.0065 (16)0.0073 (16)−0.0065 (16)
C60.0158 (19)0.013 (2)0.0171 (19)0.0023 (14)0.0038 (15)0.0000 (15)
C70.019 (2)0.011 (2)0.020 (2)0.0009 (15)0.0044 (16)0.0032 (15)
C80.0137 (19)0.018 (2)0.019 (2)0.0009 (15)0.0003 (15)0.0000 (16)
C90.019 (2)0.029 (3)0.024 (2)−0.0038 (17)0.0038 (17)−0.0036 (18)
C100.020 (2)0.030 (3)0.020 (2)−0.0046 (17)0.0007 (17)−0.0026 (18)
C110.017 (2)0.031 (3)0.025 (2)−0.0019 (17)0.0021 (17)0.0012 (19)
C120.021 (2)0.034 (3)0.021 (2)0.0016 (18)0.0025 (17)−0.0024 (19)
C130.020 (2)0.0084 (19)0.026 (2)0.0012 (15)0.0073 (17)−0.0038 (16)
C140.020 (2)0.013 (2)0.020 (2)−0.0019 (15)0.0047 (16)−0.0020 (16)
C150.021 (2)0.016 (2)0.025 (2)−0.0002 (16)0.0051 (17)−0.0003 (17)
C160.016 (2)0.027 (2)0.023 (2)−0.0009 (17)0.0006 (16)−0.0026 (18)
C170.025 (2)0.041 (3)0.033 (3)−0.007 (2)0.011 (2)0.005 (2)
C180.025 (2)0.046 (3)0.018 (2)−0.005 (2)0.0044 (18)0.001 (2)
C190.0194 (19)0.0101 (19)0.0167 (19)−0.0020 (15)0.0055 (15)−0.0018 (15)
C200.0160 (18)0.0079 (19)0.0165 (19)0.0006 (14)0.0052 (14)−0.0035 (14)
C210.022 (2)0.015 (2)0.0075 (17)0.0018 (15)0.0015 (14)−0.0012 (14)
C220.028 (2)0.016 (2)0.0123 (18)−0.0059 (16)0.0021 (16)−0.0051 (15)
C230.023 (2)0.013 (2)0.018 (2)−0.0047 (15)0.0039 (16)−0.0005 (16)
C240.0185 (19)0.0119 (19)0.0139 (18)0.0004 (15)0.0019 (15)0.0010 (15)
Br1—C41.885 (4)C3—C41.380 (5)
Br2—C101.881 (4)C3—H3B0.9600
Br3—C161.885 (4)C4—C5iii1.394 (5)
Br4—C221.887 (4)C5—C4iv1.394 (5)
Cu1—O11.957 (3)C5—H5A0.8971
Cu1—O21.958 (3)C6—C2iv1.386 (5)
Cu1—O31.969 (3)C6—H6A0.9065
Cu1—O41.979 (3)C7—O2i1.257 (5)
Cu1—N12.150 (3)C7—C81.494 (5)
Cu1—Cu1i2.6355 (10)C8—C121.385 (6)
Cu2—O61.952 (3)C8—C91.390 (6)
Cu2—O81.965 (3)C9—C101.389 (5)
Cu2—O71.973 (3)C9—H9A0.9601
Cu2—O51.976 (3)C10—C111.375 (6)
Cu2—N32.164 (3)C11—H11A0.9599
Cu2—Cu2ii2.6423 (10)C12—H12A0.9601
N1—C51.336 (5)C13—O8ii1.254 (5)
N1—C61.338 (5)C13—C141.500 (5)
N2—C121.333 (5)C14—C151.385 (6)
N2—C111.337 (5)C14—C181.386 (6)
N3—C231.327 (5)C15—C161.379 (6)
N3—C241.332 (5)C15—H15A0.9600
N4—C181.343 (6)C16—C171.376 (6)
N4—C171.347 (6)C17—H17A0.9601
O1—C71.247 (5)C18—H18A0.9600
O2—C7i1.257 (5)C19—O6ii1.254 (4)
O3—C1i1.263 (5)C19—C201.492 (5)
O4—C11.250 (4)C20—C24v1.376 (5)
O5—C191.258 (4)C20—C211.390 (5)
O6—C19ii1.254 (4)C21—C22v1.373 (5)
O7—C131.258 (5)C21—H21A0.9821
O8—C13ii1.254 (5)C22—C21vi1.373 (5)
C1—O3i1.263 (5)C22—C231.381 (5)
C1—C21.494 (5)C23—H23A0.9600
C2—C6iii1.386 (5)C24—C20vi1.376 (5)
C2—C31.386 (5)C24—H24A0.9814
O1—Cu1—O2167.78 (12)N1—C5—H5A119.1
O1—Cu1—O389.88 (13)C4iv—C5—H5A119.5
O2—Cu1—O390.95 (12)N1—C6—C2iv123.0 (4)
O1—Cu1—O488.36 (13)N1—C6—H6A116.4
O2—Cu1—O488.40 (12)C2iv—C6—H6A120.7
O3—Cu1—O4168.51 (11)O1—C7—O2i126.1 (4)
O1—Cu1—N198.55 (12)O1—C7—C8117.0 (3)
O2—Cu1—N193.55 (12)O2i—C7—C8116.9 (3)
O3—Cu1—N194.02 (11)C12—C8—C9118.3 (4)
O4—Cu1—N197.47 (11)C12—C8—C7121.3 (4)
O1—Cu1—Cu1i86.23 (9)C9—C8—C7120.4 (3)
O2—Cu1—Cu1i81.90 (9)C10—C9—C8117.7 (4)
O3—Cu1—Cu1i80.33 (8)C10—C9—H9A121.1
O4—Cu1—Cu1i88.23 (8)C8—C9—H9A121.2
N1—Cu1—Cu1i172.64 (9)C11—C10—C9120.1 (4)
O6—Cu2—O889.09 (13)C11—C10—Br2119.6 (3)
O6—Cu2—O790.52 (13)C9—C10—Br2120.3 (3)
O8—Cu2—O7168.27 (11)N2—C11—C10122.3 (4)
O6—Cu2—O5168.22 (11)N2—C11—H11A118.9
O8—Cu2—O589.85 (12)C10—C11—H11A118.8
O7—Cu2—O588.14 (12)N2—C12—C8123.7 (4)
O6—Cu2—N395.31 (12)N2—C12—H12A118.3
O8—Cu2—N399.66 (12)C8—C12—H12A118.0
O7—Cu2—N392.04 (12)O8ii—C13—O7126.4 (4)
O5—Cu2—N396.44 (11)O8ii—C13—C14117.3 (3)
O6—Cu2—Cu2ii82.01 (8)O7—C13—C14116.2 (4)
O8—Cu2—Cu2ii85.86 (9)C15—C14—C18119.1 (4)
O7—Cu2—Cu2ii82.48 (9)C15—C14—C13120.8 (4)
O5—Cu2—Cu2ii86.21 (8)C18—C14—C13120.0 (4)
N3—Cu2—Cu2ii173.85 (9)C16—C15—C14117.2 (4)
C5—N1—C6118.8 (3)C16—C15—H15A121.5
C5—N1—Cu1125.1 (3)C14—C15—H15A121.4
C6—N1—Cu1115.9 (2)C17—C16—C15120.8 (4)
C12—N2—C11117.8 (4)C17—C16—Br3118.9 (3)
C23—N3—C24118.6 (3)C15—C16—Br3120.3 (3)
C23—N3—Cu2125.9 (3)N4—C17—C16122.7 (4)
C24—N3—Cu2115.5 (2)N4—C17—H17A118.7
C18—N4—C17116.5 (4)C16—C17—H17A118.6
C7—O1—Cu1120.4 (3)N4—C18—C14123.8 (4)
C7i—O2—Cu1125.2 (3)N4—C18—H18A117.9
C1i—O3—Cu1127.1 (2)C14—C18—H18A118.3
C1—O4—Cu1117.7 (2)O6ii—C19—O5126.2 (4)
C19—O5—Cu2119.7 (2)O6ii—C19—C20115.6 (3)
C19ii—O6—Cu2125.9 (3)O5—C19—C20118.2 (3)
C13—O7—Cu2124.3 (3)C24v—C20—C21118.6 (3)
C13ii—O8—Cu2120.8 (2)C24v—C20—C19119.6 (3)
O4—C1—O3i126.5 (4)C21—C20—C19121.8 (3)
O4—C1—C2118.1 (3)C22v—C21—C20117.5 (3)
O3i—C1—C2115.2 (3)C22v—C21—H21A122.2
C6iii—C2—C3118.6 (3)C20—C21—H21A120.3
C6iii—C2—C1119.2 (3)C21vi—C22—C23120.7 (3)
C3—C2—C1122.0 (3)C21vi—C22—Br4120.0 (3)
C4—C3—C2118.4 (4)C23—C22—Br4119.2 (3)
C4—C3—H3B120.8N3—C23—C22121.4 (4)
C2—C3—H3B120.8N3—C23—H23A119.5
C3—C4—C5iii119.9 (4)C22—C23—H23A119.2
C3—C4—Br1121.4 (3)N3—C24—C20vi123.2 (3)
C5iii—C4—Br1118.7 (3)N3—C24—H24A116.2
N1—C5—C4iv121.4 (4)C20vi—C24—H24A120.5
  4 in total

1.  Supramolecular medicinal chemistry: mixed-ligand coordination complexes.

Authors:  Zhenbo Ma; Brian Moulton
Journal:  Mol Pharm       Date:  2007-05-12       Impact factor: 4.939

2.  A short history of SHELX.

Authors:  George M Sheldrick
Journal:  Acta Crystallogr A       Date:  2007-12-21       Impact factor: 2.290

3.  A sugar discriminating binuclear copper(II) complex.

Authors:  Susanne Striegler; Michael Dittel
Journal:  J Am Chem Soc       Date:  2003-09-24       Impact factor: 15.419

4.  Binuclear copper(II) complexes with N4O3 coordinating heptadentate ligand: synthesis, structure, magnetic properties, density-functional theory study, and catecholase activity.

Authors:  Atanu Banerjee; Sumana Sarkar; Deepak Chopra; Enrique Colacio; Kajal Krishna Rajak
Journal:  Inorg Chem       Date:  2008-04-16       Impact factor: 5.165

  4 in total
  1 in total

1.  Tetra-kis(μ-5-bromo-nicotinato)-κO,O':O';κO:O,O';κO:O'-bis-[diaqua-(5-bromo-nicotinato-κO,O')neodymium(III)] dihydrate.

Authors:  Jing Huang; Jin Zhang; Hong-Ji Chen
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2011-06-25
  1 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.