Literature DB >> 23468685

{6,6'-Dimeth-oxy-2,2'-[cyclo-hexane-1,2-diylbis(nitrilo-methanylyl-idene)]diphenolato}copper(II) monohydrate.

Chunmei Hu1, Shunsheng Zhao, Xingqiang Lü, Rong Lu.   

Abstract

In the title compound, [Cu(C22H24N2O4)]·H2O, the Cu(II) atom is four-coordinated in a distorted planar geometry with a mean deviation of 0.1164 (2) Å for the plane generated by the ligating atoms of the salen-type Schiff base ligand. In the crystal, O(water)-H⋯O and C-H⋯O hydrogen bonds form a three-dimensional-network.

Entities:  

Year:  2012        PMID： 23468685      PMCID： PMC3588720          DOI： 10.1107/S1600536812044625

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


Related literature

For the synthetic method, see: Marinovich et al. (1999 ▶). For related structures, see: Tang (2009 ▶); Ji & Lu (2010 ▶).

Experimental

Crystal data

[Cu(C22H24N2O4)]·H2O M = 462.00 Monoclinic, a = 11.2116 (13) Å b = 10.5256 (12) Å c = 18.171 (7) Å β = 106.185 (2)° V = 2059.4 (9) Å3 Z = 4 Mo Kα radiation μ = 1.10 mm−1 T = 296 K 0.38 × 0.24 × 0.21 mm

Data collection

Bruker SMART 1K CCD area-detector diffractometer Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ▶) T min = 0.736, T max = 0.794 10265 measured reflections 3670 independent reflections 2859 reflections with I > 2σ(I) R int = 0.048

Refinement

R[F 2 > 2σ(F 2)] = 0.050 wR(F 2) = 0.105 S = 1.05 3670 reflections 279 parameters 3 restraints H-atom parameters constrained Δρmax = 0.30 e Å−3 Δρmin = −0.30 e Å−3 Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL and local programs. Click here for additional data file. Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812044625/qm2087sup1.cif Click here for additional data file. Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812044625/qm2087Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
[Cu(C22H24N2O4)]·H2OF(000) = 964
Mr = 462.00Dx = 1.490 Mg m−3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 5789 reflections
a = 11.2116 (13) Åθ = 1.9–25.3°
b = 10.5256 (12) ŵ = 1.10 mm−1
c = 18.171 (7) ÅT = 296 K
β = 106.185 (2)°Block, dark green
V = 2059.4 (9) Å30.38 × 0.24 × 0.21 mm
Z = 4
Bruker SMART 1K CCD area-detector diffractometer3670 independent reflections
Radiation source: fine-focus sealed tube2859 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.048
thin–slice ω scansθmax = 25.1°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)h = −13→11
Tmin = 0.736, Tmax = 0.794k = −12→8
10265 measured reflectionsl = −21→21
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.050Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.105H-atom parameters constrained
S = 1.05w = 1/[σ2(Fo2) + (0.0397P)2 + 0.7087P] where P = (Fo2 + 2Fc2)/3
3670 reflections(Δ/σ)max < 0.001
279 parametersΔρmax = 0.30 e Å−3
3 restraintsΔρmin = −0.30 e Å−3
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
Cu10.14977 (4)0.96825 (4)0.16126 (2)0.03146 (16)
N20.2322 (3)1.0281 (3)0.08566 (17)0.0313 (7)
O30.0574 (2)0.8409 (2)0.09541 (14)0.0360 (6)
O20.0640 (2)0.9319 (2)0.23616 (14)0.0395 (6)
N10.2692 (3)1.0751 (3)0.23096 (17)0.0339 (7)
C150.2008 (3)0.9961 (3)0.0149 (2)0.0336 (9)
H15A0.23631.0418−0.01750.040*
C210.0524 (3)0.8231 (3)0.0229 (2)0.0313 (8)
C80.2583 (3)1.1234 (3)0.2941 (2)0.0344 (9)
H8A0.32001.17870.32070.041*
O4−0.0811 (3)0.6552 (3)0.02914 (16)0.0543 (8)
C70.0660 (3)1.0045 (3)0.2949 (2)0.0354 (9)
C170.0985 (3)0.8705 (4)−0.0979 (2)0.0393 (9)
H17A0.13950.9201−0.12550.047*
C140.3202 (3)1.1341 (3)0.1158 (2)0.0328 (8)
H14A0.27151.21260.11020.039*
C20−0.0255 (3)0.7221 (3)−0.0167 (2)0.0379 (9)
O1−0.1149 (3)0.8971 (3)0.29982 (16)0.0559 (8)
C90.3749 (3)1.1096 (4)0.2019 (2)0.0363 (9)
H9A0.41321.18780.22700.044*
C60.1570 (3)1.0974 (3)0.3262 (2)0.0355 (9)
C160.1160 (3)0.8963 (3)−0.0194 (2)0.0305 (8)
C2−0.0302 (4)0.9896 (4)0.3321 (2)0.0437 (10)
C19−0.0380 (4)0.6995 (4)−0.0931 (2)0.0422 (10)
H19A−0.08810.6329−0.11760.051*
C22−0.1678 (4)0.5579 (4)−0.0063 (3)0.0573 (12)
H22A−0.20060.51850.03160.086*
H22B−0.12640.4951−0.02860.086*
H22C−0.23460.5949−0.04550.086*
C3−0.0340 (4)1.0629 (4)0.3934 (3)0.0576 (12)
H3A−0.09811.05160.41600.069*
C40.0569 (4)1.1547 (4)0.4227 (3)0.0609 (13)
H4A0.05341.20420.46440.073*
C180.0231 (4)0.7747 (4)−0.1342 (2)0.0440 (10)
H18A0.01250.7597−0.18610.053*
C50.1502 (4)1.1707 (4)0.3898 (2)0.0449 (10)
H5A0.21111.23140.40940.054*
C1−0.2129 (4)0.8727 (5)0.3334 (3)0.0675 (14)
H1A−0.26520.80660.30540.101*
H1B−0.26100.94860.33190.101*
H1C−0.17870.84660.38570.101*
C100.4703 (3)1.0043 (4)0.2179 (2)0.0451 (10)
H10A0.43010.92460.19880.054*
H10B0.50630.99610.27280.054*
C120.5193 (4)1.0508 (4)0.0944 (2)0.0541 (12)
H12A0.58551.07230.07180.065*
H12B0.48170.97210.07130.065*
C110.5734 (4)1.0312 (5)0.1797 (2)0.0578 (12)
H11A0.61891.10660.20220.069*
H11B0.63110.96040.18860.069*
C130.4228 (4)1.1548 (4)0.0767 (2)0.0450 (10)
H13A0.38591.15900.02170.054*
H13B0.46301.23570.09320.054*
O50.8238 (3)0.7829 (4)0.1442 (2)0.1052 (14)
HW10.85570.83780.17790.158*
HW20.87130.71940.15550.158*
U11U22U33U12U13U23
Cu10.0307 (3)0.0376 (3)0.0278 (3)−0.0044 (2)0.01097 (19)−0.0017 (2)
N20.0276 (16)0.0347 (17)0.0322 (18)0.0001 (14)0.0095 (14)0.0021 (14)
O30.0388 (15)0.0395 (15)0.0308 (15)−0.0073 (11)0.0113 (12)−0.0041 (11)
O20.0434 (16)0.0465 (16)0.0312 (15)−0.0097 (12)0.0146 (13)−0.0041 (12)
N10.0298 (17)0.0430 (18)0.0304 (18)−0.0042 (14)0.0108 (14)−0.0013 (14)
C150.028 (2)0.044 (2)0.030 (2)0.0034 (16)0.0099 (17)0.0053 (17)
C210.028 (2)0.034 (2)0.030 (2)0.0105 (16)0.0041 (16)−0.0012 (16)
C80.037 (2)0.034 (2)0.030 (2)−0.0010 (17)0.0071 (18)−0.0015 (16)
O40.0599 (19)0.0530 (18)0.054 (2)−0.0270 (15)0.0217 (16)−0.0120 (15)
C70.035 (2)0.044 (2)0.027 (2)0.0064 (17)0.0082 (17)0.0058 (17)
C170.038 (2)0.051 (3)0.030 (2)0.0096 (19)0.0106 (18)−0.0013 (18)
C140.032 (2)0.033 (2)0.033 (2)−0.0032 (16)0.0100 (17)0.0052 (16)
C200.035 (2)0.035 (2)0.044 (3)0.0029 (17)0.0099 (19)−0.0040 (19)
O10.0469 (18)0.079 (2)0.0491 (19)−0.0161 (16)0.0258 (15)0.0005 (16)
C90.030 (2)0.047 (2)0.035 (2)−0.0065 (17)0.0123 (17)−0.0061 (18)
C60.035 (2)0.041 (2)0.029 (2)0.0036 (17)0.0070 (17)0.0018 (17)
C160.027 (2)0.034 (2)0.030 (2)0.0075 (16)0.0090 (16)0.0016 (16)
C20.040 (2)0.057 (3)0.037 (2)0.000 (2)0.016 (2)0.005 (2)
C190.035 (2)0.042 (2)0.044 (3)0.0041 (18)0.0027 (19)−0.0119 (19)
C220.051 (3)0.048 (3)0.068 (3)−0.017 (2)0.009 (2)−0.001 (2)
C30.057 (3)0.081 (4)0.047 (3)0.005 (3)0.033 (2)0.000 (2)
C40.071 (3)0.074 (3)0.046 (3)0.007 (3)0.031 (3)−0.013 (2)
C180.040 (2)0.057 (3)0.031 (2)0.010 (2)0.0042 (19)−0.009 (2)
C50.053 (3)0.049 (3)0.035 (2)0.005 (2)0.017 (2)−0.0049 (19)
C10.043 (3)0.112 (4)0.054 (3)−0.007 (3)0.025 (2)0.016 (3)
C100.036 (2)0.059 (3)0.038 (2)0.0092 (19)0.0068 (19)0.0102 (19)
C120.041 (2)0.081 (3)0.046 (3)0.000 (2)0.020 (2)0.000 (2)
C110.036 (2)0.089 (3)0.049 (3)0.009 (2)0.013 (2)0.007 (2)
C130.041 (2)0.055 (3)0.041 (3)−0.016 (2)0.014 (2)0.0015 (19)
O50.083 (3)0.152 (4)0.093 (3)−0.045 (3)0.045 (2)−0.037 (3)
Cu1—O31.900 (2)C9—H9A0.9800
Cu1—O21.912 (2)C6—C51.409 (5)
Cu1—N11.928 (3)C2—C31.366 (5)
Cu1—N21.961 (3)C19—C181.393 (5)
N2—C151.280 (4)C19—H19A0.9300
N2—C141.490 (4)C22—H22A0.9600
O3—C211.317 (4)C22—H22B0.9600
O2—C71.308 (4)C22—H22C0.9600
N1—C81.292 (4)C3—C41.398 (6)
N1—C91.472 (4)C3—H3A0.9300
C15—C161.438 (5)C4—C51.353 (5)
C15—H15A0.9300C4—H4A0.9300
C21—C161.413 (5)C18—H18A0.9300
C21—C201.436 (5)C5—H5A0.9300
C8—C61.439 (5)C1—H1A0.9600
C8—H8A0.9300C1—H1B0.9600
O4—C201.367 (4)C1—H1C0.9600
O4—C221.436 (4)C10—C111.532 (5)
C7—C61.413 (5)C10—H10A0.9700
C7—C21.433 (5)C10—H10B0.9700
C17—C181.361 (5)C12—C131.510 (5)
C17—C161.411 (5)C12—C111.513 (6)
C17—H17A0.9300C12—H12A0.9700
C14—C131.527 (5)C12—H12B0.9700
C14—C91.534 (5)C11—H11A0.9700
C14—H14A0.9800C11—H11B0.9700
C20—C191.375 (5)C13—H13A0.9700
O1—C21.373 (5)C13—H13B0.9700
O1—C11.422 (4)O5—HW10.8458
C9—C101.511 (5)O5—HW20.8437
O3—Cu1—O290.74 (10)O1—C2—C7113.5 (3)
O3—Cu1—N1169.18 (11)C20—C19—C18121.0 (4)
O2—Cu1—N192.53 (11)C20—C19—H19A119.5
O3—Cu1—N293.78 (11)C18—C19—H19A119.5
O2—Cu1—N2172.77 (11)O4—C22—H22A109.5
N1—Cu1—N284.05 (12)O4—C22—H22B109.5
C15—N2—C14122.4 (3)H22A—C22—H22B109.5
C15—N2—Cu1124.6 (2)O4—C22—H22C109.5
C14—N2—Cu1112.1 (2)H22A—C22—H22C109.5
C21—O3—Cu1126.5 (2)H22B—C22—H22C109.5
C7—O2—Cu1124.5 (2)C2—C3—C4121.0 (4)
C8—N1—C9120.5 (3)C2—C3—H3A119.5
C8—N1—Cu1126.4 (2)C4—C3—H3A119.5
C9—N1—Cu1112.9 (2)C5—C4—C3119.3 (4)
N2—C15—C16126.2 (3)C5—C4—H4A120.3
N2—C15—H15A116.9C3—C4—H4A120.3
C16—C15—H15A116.9C17—C18—C19119.5 (4)
O3—C21—C16125.4 (3)C17—C18—H18A120.2
O3—C21—C20117.2 (3)C19—C18—H18A120.2
C16—C21—C20117.4 (3)C4—C5—C6121.3 (4)
N1—C8—C6124.5 (3)C4—C5—H5A119.3
N1—C8—H8A117.8C6—C5—H5A119.3
C6—C8—H8A117.8O1—C1—H1A109.5
C20—O4—C22117.5 (3)O1—C1—H1B109.5
O2—C7—C6125.4 (3)H1A—C1—H1B109.5
O2—C7—C2118.5 (3)O1—C1—H1C109.5
C6—C7—C2116.1 (3)H1A—C1—H1C109.5
C18—C17—C16121.6 (4)H1B—C1—H1C109.5
C18—C17—H17A119.2C9—C10—C11111.1 (3)
C16—C17—H17A119.2C9—C10—H10A109.4
N2—C14—C13116.3 (3)C11—C10—H10A109.4
N2—C14—C9106.6 (3)C9—C10—H10B109.4
C13—C14—C9111.1 (3)C11—C10—H10B109.4
N2—C14—H14A107.5H10A—C10—H10B108.0
C13—C14—H14A107.5C13—C12—C11112.1 (4)
C9—C14—H14A107.5C13—C12—H12A109.2
O4—C20—C19126.2 (4)C11—C12—H12A109.2
O4—C20—C21113.1 (3)C13—C12—H12B109.2
C19—C20—C21120.7 (4)C11—C12—H12B109.2
C2—O1—C1118.0 (3)H12A—C12—H12B107.9
N1—C9—C10110.3 (3)C12—C11—C10110.6 (3)
N1—C9—C14105.9 (3)C12—C11—H11A109.5
C10—C9—C14112.3 (3)C10—C11—H11A109.5
N1—C9—H9A109.4C12—C11—H11B109.5
C10—C9—H9A109.4C10—C11—H11B109.5
C14—C9—H9A109.4H11A—C11—H11B108.1
C5—C6—C7120.7 (3)C12—C13—C14112.6 (3)
C5—C6—C8117.2 (3)C12—C13—H13A109.1
C7—C6—C8122.1 (3)C14—C13—H13A109.1
C17—C16—C21119.7 (3)C12—C13—H13B109.1
C17—C16—C15117.9 (3)C14—C13—H13B109.1
C21—C16—C15122.4 (3)H13A—C13—H13B107.8
C3—C2—O1125.0 (4)HW1—O5—HW2104.7
C3—C2—C7121.5 (4)
D—H···AD—HH···AD···AD—H···A
O5—HW1···O1i0.852.242.971 (5)146
O5—HW1···O2i0.852.483.161 (4)138
C8—H8A···O3ii0.932.443.352 (4)166
C9—H9A···O2ii0.982.653.579 (5)159
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A D—HH⋯A D⋯A D—H⋯A
O5—HW1⋯O1i 0.852.242.971 (5)146
O5—HW1⋯O2i 0.852.483.161 (4)138
C8—H8A⋯O3ii 0.932.443.352 (4)166
C9—H9A⋯O2ii 0.982.653.579 (5)159

Symmetry codes: (i) ; (ii) .

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