metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890

catena-Poly[[aqua­bis­­{4-[2-(2,4-dioxo­pentan-3-yl­­idene)hydrazin-1-yl]benzo­ato-κO}copper(II)]-μ-N,N-di­ethyl­pyridine-3-carboxamide-κ2N1:O]

aDepartment of Organic Chemistry, Baku State University, Baku, Azerbaijan, and bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, and, Chemistry Department, Faculty of Science, King Abdulaziz University, PO Box 80203 Jeddah, Saudi Arabia
*Correspondence e-mail: seikweng@um.edu.my

(Received 25 December 2011; accepted 1 January 2012; online 11 January 2012)

The CuII atom in the title compound, [Cu(C12H11N2O4)2(C10H14N2O)(H2O)]n, lies in a square plane defined by the O atoms of the carboxyl­ate ions, the N atom of the N-heterocycle and the water mol­ecule. Coordination by an amido O atom of an adjacent N-heterocycle in the apical direction leads to a polymeric chain running along [01[\overline{1}]]. The chain motif is consolidated by hydrogen bonds involving the water mol­ecule; the water mol­ecule is a hydrogen-bond donor to the free carbonyl atoms of the carboxyl­ate ions. Intra­molecular N—H⋯O hydrogen bonds also occur.

Related literature

For a related structure, see: Maharramov et al. (2011[Maharramov, A. M., Mardanova, V. I., Chyraqov, F., Gurbanov, A. V. & Ng, S. W. (2011). Acta Cryst. E67, m708-m709.]).

[Scheme 1]

Experimental

Crystal data
  • [Cu(C12H11N2O4)2(C10H14N2O)(H2O)]

  • Mr = 754.24

  • Monoclinic, P 21 /c

  • a = 17.0586 (8) Å

  • b = 8.5289 (4) Å

  • c = 24.8249 (12) Å

  • β = 101.431 (1)°

  • V = 3540.2 (3) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.68 mm−1

  • T = 296 K

  • 0.30 × 0.20 × 0.20 mm

Data collection
  • Bruker SMART APEX diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.822, Tmax = 0.876

  • 40068 measured reflections

  • 8845 independent reflections

  • 6058 reflections with I > 2σ(I)

  • Rint = 0.052

Refinement
  • R[F2 > 2σ(F2)] = 0.045

  • wR(F2) = 0.131

  • S = 1.00

  • 8845 reflections

  • 480 parameters

  • 4 restraints

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 1.14 e Å−3

  • Δρmin = −0.39 e Å−3

Table 1
Selected bond lengths (Å)

Cu1—O1 1.9409 (16)
Cu1—O1W 1.9706 (18)
Cu1—O5 1.9278 (17)
Cu1—O9i 2.4505 (17)
Cu1—N5 2.032 (2)
Symmetry code: (i) [-x+1, y-{\script{1\over 2}}, -z+{\script{3\over 2}}].

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O1w—H11⋯O2ii 0.84 (1) 1.88 (1) 2.700 (2) 163 (4)
O1w—H12⋯O6ii 0.84 (1) 1.88 (1) 2.705 (3) 171 (3)
N1—H1⋯O3 0.88 (1) 1.84 (2) 2.552 (3) 138 (3)
N3—H3⋯O7 0.88 (1) 1.85 (2) 2.559 (3) 137 (3)
Symmetry code: (ii) -x+1, -y+1, -z+1.

Data collection: APEX2 (Bruker, 2005[Bruker (2005). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2005[Bruker (2005). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: X-SEED (Barbour, 2001[Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.]); software used to prepare material for publication: publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).

Supporting information


Comment top

We have been investigating the adducts of 3-diethylpridine-3-carboxamide with copper(II) salts; a previous study reported the copper bis(thienoylacetonate) adduct (Maharramov et al., 2011). The reaction of the N-heterocycle with copper bis(4-[(2,4-dioxopentan-3-yl)diazenyl]benzoate in the presence of sodium bicarbonate yielded the title monoaqua mono-adduct (Scheme I). The CuII atom lies in a square plane defined by the O atom of the carboxylate ions, the N atom of the N-heterocycle and the water molecule; coordination by the amido O atom of an adjacent N-heterocycle leads to a linear chain running along [0 1 - 1]. The chain motif is consolidated by hydrogen bonds that involve the water molecule; the water molecule is hydrogen-bond donor to the the double-bond carbonyl O atom of the carboxylate ions (Table 1).

Related literature top

For a related structure, see: Maharramov et al. (2011).

Experimental top

4-[(2,4-Dioxopentan-3-yl)diazenyl]benzoic acid and N,N-diethylpyridine-3-carboxamide (cardioamine) were purchased from a chemical supplier. The carboxylic acid (0.0248 g, 0.01 mol) in water (50 ml) and an excess of cardioamine (5 ml) were added to a solution of copper acetate hydrate (0.0156 g, 0.01 mol) in water (50 ml). Sodium bicarbonate (0.01 g) was also added. The green solution was filtered and then set aside for the growth of crystals within a week; yield 70%.

Refinement top

Carbon-bound H-atoms were placed in calculated positions [C–H 0.93 to 0.98 Å; U(H) 1.2 to 1.5U(C)] and were included in the refinement in the riding model approximation.

The water and amino- H-atoms were located in a difference Fourier map, and were refined with distance restraints of O–H 0.84±0.01 and N–H 0.88 + 0.01 Å; their temperature factors were refined.

Omitted were (1 0 0), (-2 1 0) and (4 1 9).

The final difference Fourier map had a peak at 2.27 Å from H25.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top
[Figure 1] Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of the repeat unit of polymeric Cu(H2O)(C10H14N2O)(C12H11N2O4)2 at the 50% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.
catena-Poly[[aquabis{4-[2-(2,4-dioxopentan-3-ylidene)hydrazin- 1-yl]benzoato-κO}copper(II)]-µ-N,N-diethylpyridine- 3-carboxamide-κ2N1:O] top
Crystal data top
[Cu(C12H11N2O4)2(C10H14N2O)(H2O)]F(000) = 1572
Mr = 754.24Dx = 1.415 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 5695 reflections
a = 17.0586 (8) Åθ = 2.3–25.5°
b = 8.5289 (4) ŵ = 0.68 mm1
c = 24.8249 (12) ÅT = 296 K
β = 101.431 (1)°Prism, green
V = 3540.2 (3) Å30.30 × 0.20 × 0.20 mm
Z = 4
Data collection top
Bruker SMART APEX
diffractometer
8845 independent reflections
Radiation source: fine-focus sealed tube6058 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.052
ϕ and ω scansθmax = 28.4°, θmin = 1.9°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 2222
Tmin = 0.822, Tmax = 0.876k = 1111
40068 measured reflectionsl = 3333
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.045Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.131H atoms treated by a mixture of independent and constrained refinement
S = 1.00 w = 1/[σ2(Fo2) + (0.0692P)2 + 0.8919P]
where P = (Fo2 + 2Fc2)/3
8845 reflections(Δ/σ)max = 0.001
480 parametersΔρmax = 1.14 e Å3
4 restraintsΔρmin = 0.39 e Å3
Crystal data top
[Cu(C12H11N2O4)2(C10H14N2O)(H2O)]V = 3540.2 (3) Å3
Mr = 754.24Z = 4
Monoclinic, P21/cMo Kα radiation
a = 17.0586 (8) ŵ = 0.68 mm1
b = 8.5289 (4) ÅT = 296 K
c = 24.8249 (12) Å0.30 × 0.20 × 0.20 mm
β = 101.431 (1)°
Data collection top
Bruker SMART APEX
diffractometer
8845 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
6058 reflections with I > 2σ(I)
Tmin = 0.822, Tmax = 0.876Rint = 0.052
40068 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0454 restraints
wR(F2) = 0.131H atoms treated by a mixture of independent and constrained refinement
S = 1.00Δρmax = 1.14 e Å3
8845 reflectionsΔρmin = 0.39 e Å3
480 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cu10.493965 (16)0.51736 (4)0.599200 (11)0.03106 (10)
O10.38597 (10)0.4339 (2)0.58434 (7)0.0385 (4)
O20.36751 (10)0.6083 (2)0.51632 (8)0.0442 (5)
O30.09251 (12)0.1214 (3)0.49904 (9)0.0619 (6)
O40.21233 (15)0.3194 (4)0.35319 (11)0.0928 (9)
O50.60299 (10)0.5906 (2)0.61634 (7)0.0422 (4)
O60.58603 (12)0.7412 (2)0.54181 (8)0.0535 (5)
O71.06507 (12)1.0617 (3)0.62687 (9)0.0588 (6)
O81.18499 (14)0.8684 (3)0.77257 (11)0.0837 (8)
O90.47008 (12)0.8486 (2)0.81977 (7)0.0452 (5)
O1W0.52061 (10)0.3639 (2)0.54628 (7)0.0348 (4)
H110.5605 (14)0.383 (4)0.5322 (14)0.078 (12)*
H120.4840 (13)0.333 (4)0.5210 (9)0.057 (9)*
N10.02254 (12)0.2933 (3)0.48185 (9)0.0394 (5)
H10.0014 (18)0.230 (3)0.5028 (11)0.066 (11)*
N20.02628 (12)0.3447 (3)0.43803 (9)0.0381 (5)
N30.94860 (12)0.8959 (3)0.64613 (9)0.0378 (5)
H30.9672 (16)0.968 (3)0.6270 (10)0.046 (8)*
N40.99542 (13)0.8552 (3)0.69171 (9)0.0387 (5)
N50.45847 (12)0.6968 (2)0.64261 (8)0.0327 (4)
N60.38353 (12)0.6457 (2)0.80156 (8)0.0354 (5)
C10.34316 (14)0.5016 (3)0.54298 (10)0.0348 (6)
C20.25803 (14)0.4482 (3)0.52657 (10)0.0321 (5)
C30.20856 (15)0.5110 (3)0.48070 (10)0.0361 (5)
H3A0.22870.58680.46020.043*
C40.13017 (15)0.4639 (3)0.46470 (10)0.0366 (6)
H40.09730.50780.43400.044*
C50.10120 (14)0.3492 (3)0.49539 (10)0.0338 (5)
C60.14959 (15)0.2853 (3)0.54144 (10)0.0372 (6)
H60.12950.20960.56200.045*
C70.22789 (14)0.3345 (3)0.55682 (10)0.0364 (6)
H70.26060.29100.58760.044*
C80.22150 (17)0.1321 (4)0.44365 (15)0.0579 (8)
H8A0.23430.06750.47240.087*
H8B0.23090.07430.40980.087*
H8C0.25450.22410.43950.087*
C90.13527 (16)0.1793 (3)0.45812 (12)0.0440 (6)
C100.10051 (15)0.2932 (3)0.42495 (11)0.0386 (6)
C110.14498 (19)0.3630 (4)0.37323 (12)0.0520 (8)
C120.1043 (2)0.4850 (4)0.34495 (14)0.0651 (9)
H12A0.13960.51780.31180.098*
H12B0.05650.44180.33610.098*
H12C0.09080.57360.36890.098*
C130.62698 (14)0.6884 (3)0.58437 (11)0.0356 (6)
C140.71265 (14)0.7415 (3)0.60170 (10)0.0328 (5)
C150.74303 (15)0.8525 (3)0.57086 (11)0.0377 (6)
H150.71040.89390.53960.045*
C160.82117 (15)0.9025 (3)0.58593 (11)0.0399 (6)
H160.84130.97690.56490.048*
C170.86936 (14)0.8412 (3)0.63267 (10)0.0342 (5)
C180.83995 (15)0.7296 (3)0.66377 (11)0.0418 (6)
H180.87260.68820.69500.050*
C190.76182 (15)0.6802 (3)0.64811 (11)0.0397 (6)
H190.74190.60490.66890.048*
C201.18795 (18)1.0784 (4)0.68823 (14)0.0606 (9)
H20A1.19981.14890.66080.091*
H20B1.22500.99250.69270.091*
H20C1.19241.13320.72250.091*
C211.10464 (16)1.0172 (3)0.67061 (12)0.0421 (6)
C221.06958 (15)0.9084 (3)0.70478 (11)0.0382 (6)
C231.11461 (18)0.8444 (4)0.75726 (13)0.0512 (7)
C241.0711 (3)0.7474 (6)0.79232 (17)0.0967 (15)
H24A1.10560.72820.82720.145*
H24B1.05570.64930.77440.145*
H24C1.02430.80260.79780.145*
C250.44230 (16)0.8393 (3)0.62092 (11)0.0418 (6)
H250.44710.85630.58470.050*
C260.41883 (17)0.9619 (3)0.65009 (12)0.0440 (6)
H260.40891.06030.63400.053*
C270.41020 (15)0.9366 (3)0.70357 (11)0.0394 (6)
H270.39411.01760.72400.047*
C280.42588 (14)0.7884 (3)0.72654 (10)0.0323 (5)
C290.44957 (14)0.6726 (3)0.69416 (10)0.0336 (5)
H290.45980.57290.70910.040*
C300.42650 (14)0.7627 (3)0.78670 (10)0.0320 (5)
C310.32376 (16)0.5548 (4)0.76355 (12)0.0465 (7)
H31A0.31360.60600.72800.056*
H31B0.27410.55450.77700.056*
C320.3491 (2)0.3856 (4)0.75645 (15)0.0634 (9)
H32A0.30770.33250.73120.095*
H32B0.35790.33320.79130.095*
H32C0.39760.38470.74230.095*
C330.38618 (16)0.6195 (3)0.86053 (10)0.0408 (6)
H33A0.43780.65290.88120.049*
H33B0.38070.50820.86700.049*
C340.32118 (18)0.7069 (4)0.88098 (12)0.0519 (7)
H34A0.32550.68710.91950.078*
H34B0.26990.67200.86140.078*
H34C0.32670.81720.87510.078*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cu10.02397 (14)0.04335 (19)0.02612 (15)0.00660 (12)0.00558 (11)0.00480 (13)
O10.0271 (8)0.0519 (11)0.0363 (10)0.0081 (8)0.0055 (7)0.0027 (8)
O20.0340 (9)0.0530 (12)0.0489 (11)0.0100 (8)0.0161 (8)0.0013 (9)
O30.0392 (11)0.0739 (16)0.0674 (14)0.0159 (10)0.0022 (10)0.0218 (12)
O40.0618 (16)0.122 (2)0.0758 (17)0.0148 (16)0.0318 (14)0.0199 (17)
O50.0276 (9)0.0568 (12)0.0419 (10)0.0116 (8)0.0063 (8)0.0040 (9)
O60.0419 (11)0.0602 (13)0.0501 (12)0.0109 (10)0.0109 (9)0.0003 (10)
O70.0449 (11)0.0732 (15)0.0558 (13)0.0198 (11)0.0035 (10)0.0137 (11)
O80.0542 (15)0.096 (2)0.0856 (18)0.0173 (14)0.0224 (13)0.0246 (15)
O90.0571 (12)0.0449 (11)0.0342 (10)0.0156 (9)0.0103 (9)0.0121 (8)
O1W0.0274 (9)0.0501 (11)0.0264 (9)0.0045 (8)0.0041 (8)0.0046 (8)
N10.0294 (11)0.0452 (13)0.0409 (12)0.0081 (10)0.0008 (10)0.0043 (10)
N20.0331 (11)0.0387 (12)0.0413 (12)0.0009 (9)0.0042 (9)0.0041 (9)
N30.0295 (11)0.0415 (13)0.0421 (12)0.0090 (9)0.0061 (9)0.0005 (10)
N40.0328 (11)0.0407 (12)0.0417 (12)0.0065 (9)0.0050 (10)0.0042 (10)
N50.0307 (10)0.0380 (12)0.0289 (10)0.0043 (9)0.0044 (8)0.0034 (9)
N60.0334 (11)0.0401 (12)0.0308 (11)0.0040 (9)0.0013 (9)0.0010 (9)
C10.0279 (11)0.0422 (15)0.0364 (13)0.0039 (10)0.0116 (10)0.0107 (11)
C20.0269 (11)0.0382 (13)0.0324 (12)0.0055 (10)0.0086 (10)0.0071 (10)
C30.0348 (12)0.0394 (14)0.0356 (13)0.0053 (11)0.0105 (10)0.0015 (11)
C40.0331 (12)0.0416 (14)0.0332 (13)0.0031 (11)0.0020 (10)0.0007 (11)
C50.0275 (12)0.0407 (14)0.0333 (13)0.0057 (10)0.0061 (10)0.0059 (10)
C60.0333 (13)0.0419 (15)0.0367 (14)0.0083 (11)0.0079 (11)0.0031 (11)
C70.0302 (12)0.0440 (15)0.0345 (13)0.0045 (11)0.0049 (10)0.0006 (11)
C80.0338 (15)0.059 (2)0.076 (2)0.0093 (13)0.0010 (15)0.0034 (16)
C90.0321 (13)0.0421 (15)0.0548 (17)0.0037 (11)0.0018 (13)0.0067 (13)
C100.0317 (13)0.0380 (14)0.0420 (14)0.0002 (11)0.0024 (11)0.0051 (11)
C110.0528 (18)0.0535 (18)0.0440 (16)0.0077 (14)0.0039 (14)0.0073 (14)
C120.083 (3)0.059 (2)0.0496 (18)0.0086 (18)0.0040 (17)0.0061 (15)
C130.0285 (12)0.0381 (14)0.0392 (14)0.0038 (10)0.0041 (11)0.0158 (11)
C140.0287 (12)0.0382 (14)0.0321 (12)0.0042 (10)0.0076 (10)0.0104 (10)
C150.0344 (13)0.0409 (14)0.0361 (13)0.0021 (11)0.0028 (11)0.0024 (11)
C160.0378 (14)0.0411 (15)0.0413 (15)0.0089 (11)0.0094 (12)0.0011 (12)
C170.0252 (11)0.0391 (14)0.0386 (13)0.0065 (10)0.0069 (10)0.0071 (11)
C180.0322 (13)0.0541 (17)0.0371 (14)0.0097 (12)0.0022 (11)0.0045 (12)
C190.0324 (13)0.0503 (16)0.0363 (14)0.0105 (11)0.0064 (11)0.0015 (12)
C200.0432 (16)0.076 (2)0.061 (2)0.0259 (16)0.0066 (15)0.0003 (17)
C210.0358 (13)0.0438 (15)0.0466 (16)0.0063 (12)0.0078 (12)0.0058 (12)
C220.0324 (13)0.0379 (14)0.0425 (14)0.0046 (11)0.0033 (11)0.0062 (11)
C230.0487 (17)0.0465 (17)0.0536 (18)0.0048 (13)0.0015 (14)0.0024 (14)
C240.084 (3)0.125 (4)0.075 (3)0.022 (3)0.000 (2)0.047 (3)
C250.0422 (15)0.0506 (17)0.0319 (13)0.0044 (12)0.0053 (11)0.0031 (12)
C260.0452 (15)0.0383 (15)0.0464 (16)0.0037 (12)0.0042 (13)0.0068 (12)
C270.0360 (13)0.0376 (14)0.0428 (15)0.0029 (11)0.0032 (11)0.0066 (11)
C280.0278 (12)0.0359 (13)0.0321 (12)0.0019 (10)0.0031 (10)0.0036 (10)
C290.0332 (12)0.0350 (13)0.0315 (12)0.0013 (10)0.0037 (10)0.0015 (10)
C300.0315 (12)0.0323 (13)0.0324 (12)0.0030 (10)0.0067 (10)0.0035 (10)
C310.0357 (14)0.0605 (19)0.0407 (15)0.0126 (13)0.0016 (12)0.0046 (13)
C320.071 (2)0.053 (2)0.068 (2)0.0277 (17)0.0191 (18)0.0169 (16)
C330.0461 (15)0.0406 (15)0.0345 (14)0.0042 (12)0.0054 (12)0.0042 (11)
C340.0499 (17)0.0605 (19)0.0481 (17)0.0026 (14)0.0168 (14)0.0016 (14)
Geometric parameters (Å, º) top
Cu1—O11.9409 (16)C11—C121.500 (5)
Cu1—O1W1.9706 (18)C12—H12A0.9600
Cu1—O51.9278 (17)C12—H12B0.9600
Cu1—O9i2.4505 (17)C12—H12C0.9600
Cu1—N52.032 (2)C13—C141.509 (3)
O1—C11.274 (3)C14—C151.382 (3)
O2—C11.244 (3)C14—C191.386 (4)
O3—C91.230 (3)C15—C161.379 (3)
O4—C111.216 (4)C15—H150.9300
O5—C131.273 (3)C16—C171.385 (4)
O6—C131.231 (3)C16—H160.9300
O7—C211.220 (3)C17—C181.381 (4)
O8—C231.203 (4)C18—C191.378 (3)
O9—C301.234 (3)C18—H180.9300
O1W—H110.841 (10)C19—H190.9300
O1W—H120.836 (10)C20—C211.496 (4)
N1—N21.308 (3)C20—H20A0.9600
N1—C51.401 (3)C20—H20B0.9600
N1—H10.876 (10)C20—H20C0.9600
N2—C101.319 (3)C21—C221.462 (4)
N3—N41.296 (3)C22—C231.480 (4)
N3—C171.406 (3)C23—C241.499 (5)
N3—H30.875 (10)C24—H24A0.9600
N4—C221.323 (3)C24—H24B0.9600
N5—C291.334 (3)C24—H24C0.9600
N5—C251.336 (3)C25—C261.376 (4)
N6—C301.333 (3)C25—H250.9300
N6—C311.466 (3)C26—C271.382 (4)
N6—C331.473 (3)C26—H260.9300
C1—C21.499 (3)C27—C281.390 (4)
C2—C31.384 (3)C27—H270.9300
C2—C71.386 (3)C28—C291.384 (3)
C3—C41.377 (3)C28—C301.508 (3)
C3—H3A0.9300C29—H290.9300
C4—C51.389 (3)C31—C321.527 (4)
C4—H40.9300C31—H31A0.9700
C5—C61.382 (4)C31—H31B0.9700
C6—C71.380 (3)C32—H32A0.9600
C6—H60.9300C32—H32B0.9600
C7—H70.9300C32—H32C0.9600
C8—C91.498 (4)C33—C341.505 (4)
C8—H8A0.9600C33—H33A0.9700
C8—H8B0.9600C33—H33B0.9700
C8—H8C0.9600C34—H34A0.9600
C9—C101.472 (4)C34—H34B0.9600
C10—C111.481 (4)C34—H34C0.9600
O5—Cu1—O1176.95 (8)C16—C15—H15119.7
O5—Cu1—O1W91.29 (8)C14—C15—H15119.7
O1—Cu1—O1W88.01 (7)C15—C16—C17119.5 (2)
O5—Cu1—N590.85 (8)C15—C16—H16120.3
O1—Cu1—N590.32 (8)C17—C16—H16120.3
O1W—Cu1—N5170.51 (8)C18—C17—C16120.5 (2)
O5—Cu1—O9i86.30 (8)C18—C17—N3122.3 (2)
O1—Cu1—O9i90.82 (7)C16—C17—N3117.2 (2)
O1W—Cu1—O9i95.96 (7)C19—C18—C17119.4 (2)
N5—Cu1—O9i93.40 (7)C19—C18—H18120.3
C1—O1—Cu1110.97 (15)C17—C18—H18120.3
C13—O5—Cu1119.32 (16)C18—C19—C14120.7 (2)
Cu1—O1W—H11117 (3)C18—C19—H19119.6
Cu1—O1W—H12118 (2)C14—C19—H19119.6
H11—O1W—H12107 (3)C21—C20—H20A109.5
N2—N1—C5120.5 (2)C21—C20—H20B109.5
N2—N1—H1116 (2)H20A—C20—H20B109.5
C5—N1—H1124 (2)C21—C20—H20C109.5
N1—N2—C10121.0 (2)H20A—C20—H20C109.5
N4—N3—C17121.0 (2)H20B—C20—H20C109.5
N4—N3—H3116 (2)O7—C21—C22119.7 (2)
C17—N3—H3123 (2)O7—C21—C20118.5 (3)
N3—N4—C22121.1 (2)C22—C21—C20121.7 (3)
C29—N5—C25118.3 (2)N4—C22—C21123.8 (2)
C29—N5—Cu1119.66 (17)N4—C22—C23113.2 (2)
C25—N5—Cu1122.06 (17)C21—C22—C23123.0 (2)
C30—N6—C31124.6 (2)O8—C23—C22121.8 (3)
C30—N6—C33118.6 (2)O8—C23—C24119.2 (3)
C31—N6—C33116.1 (2)C22—C23—C24119.0 (3)
O2—C1—O1124.2 (2)C23—C24—H24A109.5
O2—C1—C2119.0 (2)C23—C24—H24B109.5
O1—C1—C2116.8 (2)H24A—C24—H24B109.5
C3—C2—C7119.0 (2)C23—C24—H24C109.5
C3—C2—C1120.4 (2)H24A—C24—H24C109.5
C7—C2—C1120.6 (2)H24B—C24—H24C109.5
C4—C3—C2121.5 (2)N5—C25—C26122.5 (2)
C4—C3—H3A119.2N5—C25—H25118.7
C2—C3—H3A119.2C26—C25—H25118.7
C3—C4—C5118.5 (2)C25—C26—C27119.0 (3)
C3—C4—H4120.7C25—C26—H26120.5
C5—C4—H4120.7C27—C26—H26120.5
C6—C5—C4120.8 (2)C26—C27—C28119.2 (2)
C6—C5—N1116.8 (2)C26—C27—H27120.4
C4—C5—N1122.4 (2)C28—C27—H27120.4
C7—C6—C5119.7 (2)C29—C28—C27117.7 (2)
C7—C6—H6120.1C29—C28—C30121.7 (2)
C5—C6—H6120.1C27—C28—C30120.1 (2)
C6—C7—C2120.3 (2)N5—C29—C28123.3 (2)
C6—C7—H7119.8N5—C29—H29118.4
C2—C7—H7119.8C28—C29—H29118.4
C9—C8—H8A109.5O9—C30—N6123.5 (2)
C9—C8—H8B109.5O9—C30—C28117.2 (2)
H8A—C8—H8B109.5N6—C30—C28119.2 (2)
C9—C8—H8C109.5N6—C31—C32113.4 (2)
H8A—C8—H8C109.5N6—C31—H31A108.9
H8B—C8—H8C109.5C32—C31—H31A108.9
O3—C9—C10119.2 (2)N6—C31—H31B108.9
O3—C9—C8118.9 (3)C32—C31—H31B108.9
C10—C9—C8121.9 (3)H31A—C31—H31B107.7
N2—C10—C9123.8 (2)C31—C32—H32A109.5
N2—C10—C11112.4 (3)C31—C32—H32B109.5
C9—C10—C11123.8 (2)H32A—C32—H32B109.5
O4—C11—C10120.8 (3)C31—C32—H32C109.5
O4—C11—C12120.5 (3)H32A—C32—H32C109.5
C10—C11—C12118.7 (3)H32B—C32—H32C109.5
C11—C12—H12A109.5N6—C33—C34112.4 (2)
C11—C12—H12B109.5N6—C33—H33A109.1
H12A—C12—H12B109.5C34—C33—H33A109.1
C11—C12—H12C109.5N6—C33—H33B109.1
H12A—C12—H12C109.5C34—C33—H33B109.1
H12B—C12—H12C109.5H33A—C33—H33B107.9
O6—C13—O5125.2 (2)C33—C34—H34A109.5
O6—C13—C14119.2 (2)C33—C34—H34B109.5
O5—C13—C14115.6 (2)H34A—C34—H34B109.5
C15—C14—C19119.2 (2)C33—C34—H34C109.5
C15—C14—C13119.7 (2)H34A—C34—H34C109.5
C19—C14—C13121.1 (2)H34B—C34—H34C109.5
C16—C15—C14120.7 (2)
O5—Cu1—O1—C1163.5 (14)O6—C13—C14—C19177.3 (2)
O1W—Cu1—O1—C186.75 (17)O5—C13—C14—C193.0 (3)
N5—Cu1—O1—C183.91 (17)C19—C14—C15—C160.2 (4)
O1—Cu1—O5—C13157.6 (14)C13—C14—C15—C16179.9 (2)
O1W—Cu1—O5—C1380.99 (19)C14—C15—C16—C170.4 (4)
N5—Cu1—O5—C1389.76 (19)C15—C16—C17—C180.7 (4)
C5—N1—N2—C10179.9 (2)C15—C16—C17—N3179.8 (2)
C17—N3—N4—C22179.0 (2)N4—N3—C17—C187.1 (4)
O5—Cu1—N5—C2997.88 (18)N4—N3—C17—C16173.8 (2)
O1—Cu1—N5—C2979.30 (18)C16—C17—C18—C190.4 (4)
O1W—Cu1—N5—C29159.1 (4)N3—C17—C18—C19179.5 (2)
O5—Cu1—N5—C2583.2 (2)C17—C18—C19—C140.2 (4)
O1—Cu1—N5—C2599.6 (2)C15—C14—C19—C180.4 (4)
O1W—Cu1—N5—C2519.8 (6)C13—C14—C19—C18179.8 (2)
Cu1—O1—C1—O20.9 (3)N3—N4—C22—C211.0 (4)
Cu1—O1—C1—C2179.77 (16)N3—N4—C22—C23177.8 (2)
O2—C1—C2—C33.4 (4)O7—C21—C22—N41.2 (4)
O1—C1—C2—C3177.2 (2)C20—C21—C22—N4177.8 (3)
O2—C1—C2—C7177.1 (2)O7—C21—C22—C23177.6 (3)
O1—C1—C2—C72.3 (3)C20—C21—C22—C233.5 (4)
C7—C2—C3—C40.4 (4)N4—C22—C23—O8172.6 (3)
C1—C2—C3—C4179.9 (2)C21—C22—C23—O86.2 (5)
C2—C3—C4—C50.7 (4)N4—C22—C23—C247.6 (4)
C3—C4—C5—C60.9 (4)C21—C22—C23—C24173.5 (3)
C3—C4—C5—N1179.4 (2)C29—N5—C25—C261.6 (4)
N2—N1—C5—C6178.1 (2)Cu1—N5—C25—C26179.5 (2)
N2—N1—C5—C42.3 (4)N5—C25—C26—C271.2 (4)
C4—C5—C6—C70.8 (4)C25—C26—C27—C280.4 (4)
N1—C5—C6—C7179.5 (2)C26—C27—C28—C290.0 (4)
C5—C6—C7—C20.5 (4)C26—C27—C28—C30172.7 (2)
C3—C2—C7—C60.3 (4)C25—N5—C29—C281.2 (4)
C1—C2—C7—C6179.8 (2)Cu1—N5—C29—C28179.79 (18)
N1—N2—C10—C91.6 (4)C27—C28—C29—N50.5 (4)
N1—N2—C10—C11178.5 (2)C30—C28—C29—N5172.1 (2)
O3—C9—C10—N23.9 (4)C31—N6—C30—O9171.9 (2)
C8—C9—C10—N2175.9 (3)C33—N6—C30—O91.7 (4)
O3—C9—C10—C11176.3 (3)C31—N6—C30—C2811.3 (4)
C8—C9—C10—C114.0 (4)C33—N6—C30—C28178.6 (2)
N2—C10—C11—O4174.5 (3)C29—C28—C30—O9118.7 (3)
C9—C10—C11—O45.6 (5)C27—C28—C30—O953.7 (3)
N2—C10—C11—C123.5 (4)C29—C28—C30—N658.3 (3)
C9—C10—C11—C12176.4 (3)C27—C28—C30—N6129.2 (3)
Cu1—O5—C13—O60.8 (4)C30—N6—C31—C32110.6 (3)
Cu1—O5—C13—C14178.80 (15)C33—N6—C31—C3279.0 (3)
O6—C13—C14—C152.4 (4)C30—N6—C33—C3491.6 (3)
O5—C13—C14—C15177.3 (2)C31—N6—C33—C3479.4 (3)
Symmetry code: (i) x+1, y1/2, z+3/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1w—H11···O2ii0.84 (1)1.88 (1)2.700 (2)163 (4)
O1w—H12···O6ii0.84 (1)1.88 (1)2.705 (3)171 (3)
N1—H1···O30.88 (1)1.84 (2)2.552 (3)138 (3)
N3—H3···O70.88 (1)1.85 (2)2.559 (3)137 (3)
Symmetry code: (ii) x+1, y+1, z+1.

Experimental details

Crystal data
Chemical formula[Cu(C12H11N2O4)2(C10H14N2O)(H2O)]
Mr754.24
Crystal system, space groupMonoclinic, P21/c
Temperature (K)296
a, b, c (Å)17.0586 (8), 8.5289 (4), 24.8249 (12)
β (°) 101.431 (1)
V3)3540.2 (3)
Z4
Radiation typeMo Kα
µ (mm1)0.68
Crystal size (mm)0.30 × 0.20 × 0.20
Data collection
DiffractometerBruker SMART APEX
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.822, 0.876
No. of measured, independent and
observed [I > 2σ(I)] reflections
40068, 8845, 6058
Rint0.052
(sin θ/λ)max1)0.669
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.045, 0.131, 1.00
No. of reflections8845
No. of parameters480
No. of restraints4
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)1.14, 0.39

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).

Selected bond lengths (Å) top
Cu1—O11.9409 (16)Cu1—O9i2.4505 (17)
Cu1—O1W1.9706 (18)Cu1—N52.032 (2)
Cu1—O51.9278 (17)
Symmetry code: (i) x+1, y1/2, z+3/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1w—H11···O2ii0.84 (1)1.884 (14)2.700 (2)163 (4)
O1w—H12···O6ii0.84 (1)1.875 (11)2.705 (3)171 (3)
N1—H1···O30.88 (1)1.84 (2)2.552 (3)138 (3)
N3—H3···O70.88 (1)1.85 (2)2.559 (3)137 (3)
Symmetry code: (ii) x+1, y+1, z+1.
 

Acknowledgements

We thank Baku State University and the University of Malaya for supporting this study.

References

First citationBarbour, L. J. (2001). J. Supramol. Chem. 1, 189–191.  CrossRef CAS Google Scholar
First citationBruker (2005). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationMaharramov, A. M., Mardanova, V. I., Chyraqov, F., Gurbanov, A. V. & Ng, S. W. (2011). Acta Cryst. E67, m708–m709.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationSheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationWestrip, S. P. (2010). J. Appl. Cryst. 43, 920–925.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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