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The crystal structure of the title compound, [Cu(C
7H
4NO
4)
2(C
6H
7NO)
2]
n, has been studied at 100 (2) K. The structure contains a linear polymeric chain of Cu
II atoms, which lie on centres of inversion and are doubly bridged by 3-pyridylmethanol molecules. Two coordination positions on each Cu centre are occupied by O atoms from 3-pyridylmethanol, with two other positions occupied by piridyl N atoms. Monodentate 2-nitrobenzoate anions bind to Cu in axial positions so that the copper(II) chromophore is
trans-[CuO
2N
2O′
2]. The axially bound 2-nitrobenzoate anions form strong intramolecular O—H
O hydrogen bonds with the OH groups of the 3-pyridylmethanol molecules. The resulting linear chains are held together by weak van der Waals interactions.
Supporting information
CCDC reference: 272107
Key indicators
- Single-crystal X-ray study
- T = 100 K
- Mean (C-C) = 0.002 Å
- R factor = 0.025
- wR factor = 0.065
- Data-to-parameter ratio = 12.1
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT021_ALERT_1_C Ratio Unique / Expected Reflections too High ... 1.01
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.98
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ?
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ?
PLAT164_ALERT_4_C Nr. of Refined C-H H-Atoms in Heavy-At Struct... 10
PLAT213_ALERT_2_C Atom O5 has ADP max/min Ratio ............. 3.10 oblate
PLAT220_ALERT_2_C Large Non-Solvent N Ueq(max)/Ueq(min) ... 2.53 Ratio
PLAT220_ALERT_2_C Large Non-Solvent O Ueq(max)/Ueq(min) ... 3.22 Ratio
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.03
Alert level G
REFLE01_ALERT_1_G _reflns_observed_criterion is an old dataname which has been
superseded by _reflns_threshold_expression
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
9 ALERT level C = Check and explain
1 ALERT level G = General alerts; check
3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
4 ALERT type 2 Indicator that the structure model may be wrong or deficient
1 ALERT type 3 Indicator that the structure quality may be low
2 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: CrysAlis CCD (Oxford Diffraction, 2001); cell refinement: CrysAlis RED (Oxford Diffraction, 2001); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS86 (Sheldrick, 1985); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP (Johnson, 1965); software used to prepare material for publication: WinGX (Farrugia, 1999).
Bis(3-nitrobenzoato)bis(3-pyridylmethanol-N,
O)copper(II) complex
top
Crystal data top
[Cu(C7H4NO4)2(C6H7NO)2] | Z = 1 |
Mr = 614.03 | F(000) = 315 |
Triclinic, P1 | Dx = 1.598 Mg m−3 |
a = 6.6920 (13) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 7.6470 (15) Å | Cell parameters from 25 reflections |
c = 12.997 (3) Å | θ = 3.9–11.6° |
α = 83.72 (3)° | µ = 0.92 mm−1 |
β = 77.11 (3)° | T = 100 K |
γ = 80.69 (3)° | Prism, blue |
V = 637.9 (2) Å3 | 0.4 × 0.3 × 0.2 mm |
Data collection top
Kuma KM-4 CCD diffractometer | 2788 independent reflections |
Radiation source: fine-focus sealed tube | 2663 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.018 |
ω scans | θmax = 28.3°, θmin = 3.8° |
Absorption correction: part of the refinement model (ΔF) (COSABS99; Starynowicz, 1999) | h = −8→8 |
Tmin = 0.724, Tmax = 0.831 | k = −10→6 |
4407 measured reflections | l = −17→17 |
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)] = 0.025 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.065 | All H-atom parameters refined |
S = 1.09 | w = 1/[σ2(Fo2) + (0.0342P)2 + 0.2981P] where P = (Fo2 + 2Fc2)/3 |
2788 reflections | (Δ/σ)max < 0.001 |
231 parameters | Δρmax = 0.32 e Å−3 |
0 restraints | Δρmin = −0.53 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 | Uiso*/Ueq | |
Cu | 0.0000 | 0.0000 | 0.0000 | 0.00992 (8) | |
O1 | −0.20981 (15) | 0.02994 (13) | 0.13387 (8) | 0.0134 (2) | |
O2 | −0.1009 (2) | 0.2434 (2) | 0.20548 (9) | 0.0255 (3) | |
O3 | 0.8099 (2) | −0.21625 (13) | −0.03357 (9) | 0.0141 (2) | |
O4 | −0.4264 (2) | 0.3488 (2) | 0.57250 (9) | 0.0298 (3) | |
O5 | −0.7544 (2) | 0.3383 (2) | 0.62520 (11) | 0.0432 (4) | |
N1 | −0.5903 (3) | 0.3110 (2) | 0.56077 (11) | 0.0263 (3) | |
N2 | 0.1846 (2) | −0.17808 (15) | 0.07894 (9) | 0.0104 (2) | |
C1 | −0.2230 (2) | 0.1375 (2) | 0.20391 (11) | 0.0137 (3) | |
C2 | −0.4121 (2) | 0.1379 (2) | 0.29334 (11) | 0.0141 (3) | |
C3 | −0.4140 (2) | 0.2193 (2) | 0.38455 (11) | 0.0160 (3) | |
C4 | −0.5915 (3) | 0.2279 (2) | 0.46367 (12) | 0.0196 (3) | |
C5 | −0.7680 (3) | 0.1638 (2) | 0.45455 (13) | 0.0246 (3) | |
C6 | −0.7642 (3) | 0.0825 (2) | 0.36381 (14) | 0.0243 (3) | |
C7 | −0.5856 (2) | 0.0673 (2) | 0.28352 (12) | 0.0185 (3) | |
C8 | 0.3891 (2) | −0.2106 (2) | 0.03762 (11) | 0.0106 (3) | |
C9 | 0.5250 (2) | −0.3321 (2) | 0.08491 (11) | 0.0112 (3) | |
C10 | 0.4468 (2) | −0.4207 (2) | 0.18103 (12) | 0.0161 (3) | |
C11 | 0.2363 (2) | −0.3887 (2) | 0.22432 (12) | 0.0182 (3) | |
C12 | 0.1101 (2) | −0.2670 (2) | 0.17124 (11) | 0.0137 (3) | |
C13 | 0.7501 (2) | −0.3687 (2) | 0.03120 (12) | 0.0134 (3) | |
H1 | −0.303 (3) | 0.270 (2) | 0.3900 (14) | 0.017 (4)* | |
H2 | −0.884 (3) | 0.174 (3) | 0.5109 (17) | 0.033 (5)* | |
H3 | −0.880 (3) | 0.036 (3) | 0.3554 (17) | 0.031 (5)* | |
H4 | −0.581 (3) | 0.014 (2) | 0.2206 (15) | 0.016 (4)* | |
H5 | 0.439 (3) | −0.142 (2) | −0.0258 (14) | 0.013 (4)* | |
H6 | 0.536 (3) | −0.500 (3) | 0.2169 (15) | 0.021 (5)* | |
H7 | 0.177 (3) | −0.448 (3) | 0.2883 (16) | 0.022 (5)* | |
H8 | −0.035 (3) | −0.243 (2) | 0.2004 (14) | 0.016 (4)* | |
H9 | 0.769 (3) | −0.470 (3) | −0.0096 (15) | 0.020 (5)* | |
H10 | 0.830 (3) | −0.404 (2) | 0.0864 (14) | 0.016 (4)* | |
H11 | 0.888 (4) | −0.246 (3) | −0.085 (2) | 0.039 (6)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cu | 0.00787 (12) | 0.01171 (12) | 0.00880 (12) | 0.00122 (8) | −0.00035 (8) | −0.00154 (8) |
O1 | 0.0116 (5) | 0.0160 (5) | 0.0108 (5) | 0.0014 (4) | −0.0002 (4) | −0.0022 (4) |
O2 | 0.0204 (6) | 0.0351 (7) | 0.0210 (6) | −0.0121 (5) | 0.0065 (5) | −0.0125 (5) |
O3 | 0.0110 (5) | 0.0135 (5) | 0.0162 (5) | −0.0027 (4) | 0.0020 (4) | −0.0025 (4) |
O4 | 0.0474 (8) | 0.0261 (6) | 0.0145 (6) | −0.0012 (5) | −0.0054 (5) | −0.0035 (5) |
O5 | 0.0519 (9) | 0.0447 (8) | 0.0215 (7) | −0.0060 (7) | 0.0207 (6) | −0.0125 (6) |
N1 | 0.0414 (9) | 0.0184 (6) | 0.0122 (6) | −0.0003 (6) | 0.0056 (6) | 0.0002 (5) |
N2 | 0.0096 (5) | 0.0106 (5) | 0.0109 (5) | −0.0015 (4) | −0.0018 (4) | −0.0015 (4) |
C1 | 0.0107 (6) | 0.0171 (7) | 0.0111 (6) | 0.0022 (5) | −0.0008 (5) | 0.0000 (5) |
C2 | 0.0142 (7) | 0.0129 (6) | 0.0117 (6) | 0.0019 (5) | 0.0014 (5) | 0.0009 (5) |
C3 | 0.0186 (7) | 0.0138 (6) | 0.0123 (7) | 0.0008 (5) | 0.0004 (5) | 0.0012 (5) |
C4 | 0.0276 (8) | 0.0142 (7) | 0.0113 (7) | 0.0018 (6) | 0.0037 (6) | 0.0008 (5) |
C5 | 0.0214 (8) | 0.0229 (8) | 0.0204 (8) | 0.0005 (6) | 0.0103 (6) | 0.0022 (6) |
C6 | 0.0171 (8) | 0.0274 (8) | 0.0253 (8) | −0.0058 (6) | 0.0026 (6) | 0.0005 (6) |
C7 | 0.0179 (7) | 0.0194 (7) | 0.0158 (7) | −0.0020 (6) | 0.0009 (6) | −0.0008 (6) |
C8 | 0.0098 (6) | 0.0103 (6) | 0.0121 (6) | −0.0034 (5) | −0.0010 (5) | −0.0016 (5) |
C9 | 0.0103 (6) | 0.0096 (6) | 0.0146 (6) | −0.0016 (5) | −0.0032 (5) | −0.0035 (5) |
C10 | 0.0166 (7) | 0.0143 (7) | 0.0163 (7) | 0.0014 (5) | −0.0046 (6) | 0.0016 (5) |
C11 | 0.0179 (7) | 0.0183 (7) | 0.0145 (7) | −0.0007 (6) | 0.0003 (6) | 0.0045 (5) |
C12 | 0.0109 (6) | 0.0147 (6) | 0.0137 (7) | −0.0012 (5) | 0.0010 (5) | −0.0015 (5) |
C13 | 0.0096 (6) | 0.0116 (6) | 0.0192 (7) | −0.0008 (5) | −0.0033 (5) | −0.0016 (5) |
Geometric parameters (Å, º) top
Cu—O1 | 1.9860 (12) | C3—C4 | 1.385 (2) |
Cu—O1i | 1.9860 (12) | C3—H1 | 0.91 (2) |
Cu—N2 | 2.0368 (13) | C4—C5 | 1.383 (2) |
Cu—N2i | 2.0368 (13) | C5—C6 | 1.386 (3) |
Cu—O3ii | 2.3724 (11) | C5—H2 | 0.94 (2) |
Cu—O3iii | 2.3724 (11) | C6—C7 | 1.398 (2) |
O1—C1 | 1.272 (2) | C6—H3 | 0.93 (2) |
O2—C1 | 1.245 (2) | C7—H4 | 0.95 (2) |
O3—C13 | 1.419 (2) | C8—C9 | 1.385 (2) |
O3—Cuiv | 2.3724 (11) | C8—H5 | 0.95 (2) |
O3—H11 | 0.78 (2) | C9—C10 | 1.390 (2) |
O4—N1 | 1.224 (2) | C9—C13 | 1.507 (2) |
O5—N1 | 1.226 (2) | C10—C11 | 1.387 (2) |
N1—C4 | 1.475 (2) | C10—H6 | 0.94 (2) |
N2—C12 | 1.347 (2) | C11—C12 | 1.386 (2) |
N2—C8 | 1.347 (2) | C11—H7 | 0.94 (2) |
C1—C2 | 1.515 (2) | C12—H8 | 0.95 (2) |
C2—C7 | 1.393 (2) | C13—H9 | 0.96 (2) |
C2—C3 | 1.395 (2) | C13—H10 | 0.98 (2) |
| | | |
O1—Cu—O1i | 180.0 | C5—C4—C3 | 122.71 (15) |
O1—Cu—N2 | 89.73 (5) | C5—C4—N1 | 119.36 (14) |
O1i—Cu—N2 | 90.27 (5) | C3—C4—N1 | 117.92 (15) |
O1—Cu—N2i | 90.27 (5) | C4—C5—C6 | 118.44 (14) |
O1i—Cu—N2i | 89.73 (5) | C4—C5—H2 | 118.8 (13) |
N2—Cu—N2i | 180.0 | C6—C5—H2 | 122.7 (13) |
O1—Cu—O3ii | 93.57 (5) | C5—C6—C7 | 120.3 (2) |
O1i—Cu—O3ii | 86.43 (5) | C5—C6—H3 | 120.8 (13) |
N2—Cu—O3ii | 85.86 (4) | C7—C6—H3 | 118.9 (13) |
N2i—Cu—O3ii | 94.14 (4) | C2—C7—C6 | 120.03 (15) |
O1—Cu—O3iii | 86.43 (5) | C2—C7—H4 | 118.5 (11) |
O1i—Cu—O3iii | 93.57 (5) | C6—C7—H4 | 121.4 (11) |
N2—Cu—O3iii | 94.14 (4) | N2—C8—C9 | 123.13 (13) |
N2i—Cu—O3iii | 85.86 (4) | N2—C8—H5 | 116.4 (10) |
O3ii—Cu—O3iii | 180.0 | C9—C8—H5 | 120.4 (10) |
C1—O1—Cu | 128.33 (9) | C8—C9—C10 | 118.19 (13) |
C13—O3—Cuiv | 129.04 (9) | C8—C9—C13 | 120.20 (12) |
C13—O3—H11 | 109.4 (17) | C10—C9—C13 | 121.60 (13) |
Cuiv—O3—H11 | 95.4 (17) | C11—C10—C9 | 119.22 (13) |
O4—N1—O5 | 123.7 (2) | C11—C10—H6 | 120.5 (12) |
O4—N1—C4 | 118.35 (14) | C9—C10—H6 | 120.3 (12) |
O5—N1—C4 | 118.0 (2) | C12—C11—C10 | 119.05 (13) |
C12—N2—C8 | 118.09 (12) | C12—C11—H7 | 119.2 (12) |
C12—N2—Cu | 122.56 (9) | C10—C11—H7 | 121.7 (12) |
C8—N2—Cu | 119.34 (9) | N2—C12—C11 | 122.29 (13) |
O2—C1—O1 | 127.23 (13) | N2—C12—H8 | 117.7 (11) |
O2—C1—C2 | 117.26 (13) | C11—C12—H8 | 120.0 (11) |
O1—C1—C2 | 115.50 (13) | O3—C13—C9 | 109.73 (11) |
C7—C2—C3 | 120.07 (14) | O3—C13—H9 | 111.6 (11) |
C7—C2—C1 | 121.27 (13) | C9—C13—H9 | 108.3 (11) |
C3—C2—C1 | 118.58 (13) | O3—C13—H10 | 112.8 (10) |
C4—C3—C2 | 118.37 (15) | C9—C13—H10 | 107.5 (11) |
C4—C3—H1 | 121.2 (12) | H9—C13—H10 | 106.7 (15) |
C2—C3—H1 | 120.4 (12) | | |
Symmetry codes: (i) −x, −y, −z; (ii) −x+1, −y, −z; (iii) x−1, y, z; (iv) x+1, y, z. |
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