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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 67| Part 7| July 2011| Pages m900-m901

Di­aqua­bis­­(4-bromo­benzoato-κO)bis­­(nicotinamide-κN1)copper(II)

aDepartment of Chemistry, Kafkas University, 36100 Kars, Turkey, bDepartment of Physics, Karabük University, 78050, Karabük, Turkey, and cDepartment of Physics, Hacettepe University, 06800 Beytepe, Ankara, Turkey
*Correspondence e-mail: merzifon@hacettepe.edu.tr

(Received 25 May 2011; accepted 6 June 2011; online 11 June 2011)

The asymmetric unit of the title mononuclear CuII complex, [Cu(C7H4BrO2)2(C6H6N2O)2(H2O)2], contains one half-mol­ecule, the CuII atom being located on an inversion center. The unit cell contains two nicotinamide (NA), two 4-bromo­benzoate (PBB) ligands and two coordinated water mol­ecules. The four O atoms in the equatorial plane around the CuII ion form a slightly distorted square-planar arrangement, while the slightly distorted octa­hedral coordination is completed by the two N atoms of the NA ligands in the axial positions. The dihedral angle between the carboxyl­ate group and the adjacent benzene ring is 22.17 (16)°, while the pyridine ring and the benzene ring are oriented at a dihedral angle of 82.80 (6)°. In the crystal, N—H⋯O, O—H⋯O and C—H⋯O hydrogen bonds link the mol­ecules into a three-dimensional network. A weak C—H⋯π inter­action is also observed.

Related literature

For literature on niacin, see: Krishnamachari (1974[Krishnamachari, K. A. V. R. (1974). Am. J. Clin. Nutr. 27, 108-111.]). For infomation on the nicotinic acid derivative N,N-diethyl­nicotinamide, see: Bigoli et al. (1972[Bigoli, F., Braibanti, A., Pellinghelli, M. A. & Tiripicchio, A. (1972). Acta Cryst. B28, 962-966.]). For related structures, see: Hökelek et al. (1996[Hökelek, T., Gündüz, H. & Necefoğlu, H. (1996). Acta Cryst. C52, 2470-2473.], 2009a[Hökelek, T., Dal, H., Tercan, B., Özbek, F. E. & Necefoğlu, H. (2009a). Acta Cryst. E65, m466-m467.],b[Hökelek, T., Dal, H., Tercan, B., Özbek, F. E. & Necefoğlu, H. (2009b). Acta Cryst. E65, m607-m608.]); Hökelek & Necefoğlu (1998[Hökelek, T. & Necefoğlu, H. (1998). Acta Cryst. C54, 1242-1244.], 2007[Hökelek, T. & Necefoğlu, H. (2007). Acta Cryst. E63, m821-m823.]); Necefoğlu et al. (2011[Necefoğlu, H., Maracı, A., Özbek, F. E., Tercan, B. & Hökelek, T. (2011). Acta Cryst. E67, m619-m620.]). For bond-length data, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]).

[Scheme 1]

Experimental

Crystal data
  • [Cu(C7H4BrO2)2(C6H6N2O)2(H2O)2]

  • Mr = 743.84

  • Triclinic, [P \overline 1]

  • a = 7.7072 (3) Å

  • b = 9.7536 (5) Å

  • c = 9.8471 (4) Å

  • α = 76.273 (2)°

  • β = 74.240 (2)°

  • γ = 85.024 (3)°

  • V = 691.86 (5) Å3

  • Z = 1

  • Mo Kα radiation

  • μ = 3.73 mm−1

  • T = 100 K

  • 0.41 × 0.38 × 0.35 mm

Data collection
  • Bruker Kappa APEXII CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2005[Bruker (2005). SADABS. Bruker AXS Inc. Madison, Wisconsin, USA.]) Tmin = 0.236, Tmax = 0.271

  • 11758 measured reflections

  • 3515 independent reflections

  • 3172 reflections with I > 2σ(I)

  • Rint = 0.057

Refinement
  • R[F2 > 2σ(F2)] = 0.039

  • wR(F2) = 0.108

  • S = 1.13

  • 3515 reflections

  • 203 parameters

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

  • Δρmax = 0.86 e Å−3

  • Δρmin = −1.29 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the N1/C8–C12 pyridine ring.

D—H⋯A D—H H⋯A DA D—H⋯A
N2—H21⋯O2i 0.85 (3) 2.06 (3) 2.831 (2) 151 (3)
N2—H22⋯O3ii 0.88 (3) 2.03 (3) 2.893 (3) 166 (3)
O4—H41⋯O2iii 0.87 (4) 1.86 (4) 2.718 (2) 167 (4)
O4—H42⋯O3iv 0.78 (4) 2.17 (4) 2.911 (2) 159 (4)
C6—H6⋯O2v 0.95 2.43 3.377 (3) 172
C4—H4⋯Cgvi 0.95 2.63 3.581 (3) 176
Symmetry codes: (i) -x, -y, -z+2; (ii) -x+1, -y, -z+2; (iii) -x, -y, -z+1; (iv) -x+1, -y, -z+1; (v) x+1, y, z; (vi) x, y+1, z.

Data collection: APEX2 (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc. Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). 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: Mercury (Macrae et al., 2006[Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.]); software used to prepare material for publication: WinGX publication routines (Farrugia, 1999[Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.]) and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Supporting information


Comment top

As a part of our ongoing investigations of transition metal complexes of nicotinamide (NA), one form of niacin (Krishnamachari, 1974), and/or the nicotinic acid derivative N,N-diethylnicotinamide (DENA), an important respiratory stimulant (Bigoli et al., 1972), the title compound was synthesized and its crystal structure is reported herein.

The asymmetric unit of the title mononuclear CuIIcomplex, (Fig. 1), contains one-half molecule. It consists of two nicotinamide (NA), two 4-bromobenzoate (PBB) ligands and two coordinated water molecules, all ligands coordinating in a monodentate manner. Atom Cu1 is located on an inversion center. The crystal structures of similar complexes of CuII, CoII, NiII, MnII and ZnII ions, [Cu(C7H5O2)2(C10H14N2O)2] (Hökelek et al., 1996), [Co(C6H6N2O)2(C7H4NO4)2(H2O)2] (Hökelek & Necefoğlu, 1998), [Co(C9H9O2)2(C10H14N2O)2(H2O)2] (Necefoğlu et al., 2011), [Ni(C7H4ClO2)2(C6H6N2O)2(H2O)2] (Hökelek et al., 2009a), [Mn(C9H10NO2)2(H2O)4].2H2O (Hökelek & Necefoğlu, 2007) and [Zn(C7H4BrO2)2(C6H6N2O)2(H2O)2] (Hökelek et al., 2009b) have also been reported. In the copper(II) complex mentioned above the two benzoate ions coordinate to the CuII atom as bidentate ligands, while in the other structures all the ligands coordinate in a monodentate manner.

In the title complex, the four symmetry related O atoms (O1, O1', O4 and O4') in the equatorial plane around the CuII ion form a slightly distorted square-planar arrangement, while the slightly distorted octahedral coordination is completed by the two symmetry related N atoms of the NA ligands (N1 and N1') in the axial positions. The near equalities of the C1—O1 [1.272 (3) Å] and C1—O2 [1.246 (3) Å] bonds in the carboxylate group indicate delocalized bonding arrangement, rather than localized single and double bonds. The Cu—O bond lengths are 1.9756 (16) Å (for benzoate oxygens) and 2.4199 (16) Å (for water oxygens), and the Cu—N bond length is 2.0116 (16) Å, close to standard values (Allen et al., 1987). The Cu atom is displaced out of the mean-plane of the carboxylate group (O1/C1/O2) by -0.5279 (1) Å. The dihedral angle between the planar carboxylate group and the adjacent benzene ring A (C2—C7) is 22.17 (16)°. The benzene A (C2—C7) and the pyridine B (N1/C8—C12) rings are oriented at a dihedral angle of A/B = 82.80 (6)°.

In the crystal, intermolecular N—H···O, O—H···O and C—H···O hydrogen bonds link the molecules into a three-dimensional network (Table 1). There also exists a weak C-H···π interaction (Table 1).

Related literature top

For literature on niacin, see: Krishnamachari (1974). For infomation on the nicotinic acid derivative N,N-diethylnicotinamide, see: Bigoli et al. (1972). For related structures, see: Hökelek et al. (1996, 2009a,b); Hökelek & Necefoğlu (1998, 2007); Necefoğlu et al. (2011). For bond-length data, see: Allen et al. (1987).

Experimental top

The title compound was prepared by the reaction of CuSO4.5H2O (1.23 g, 5 mmol) in H2O (20 ml) and NA (1.22 g, 10 mmol) in H2O (20 ml) with sodium 4-bromobenzoate (2.23 g, 10 mmol) in H2O (100 ml) at room temperature. The mixture was filtered and set aside to crystallize at ambient temperature for three weeks, giving blue single crystals.

Refinement top

Atoms H21 and H22 (for NH2) and H41 and H42 (for H2O) were located in a difference Fourier map and were freely refined. The C-bound H-atoms were positioned geometrically with C—H = 0.95 Å for aromatic H-atoms, and constrained to ride on their parent atoms, with Uiso(H) = 1.2Ueq(C).

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2006); software used to prepare material for publication: WinGX publication routines (Farrugia, 1999) and PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title molecule with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level [symmetry code: (') -x, -y, -z+1].
Diaquabis(4-bromobenzoato-κO)bis(nicotinamide-κN1)copper(II) top
Crystal data top
[Cu(C7H4BrO2)2(C6H6N2O)2(H2O)2]Z = 1
Mr = 743.84F(000) = 371
Triclinic, P1Dx = 1.785 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.7072 (3) ÅCell parameters from 7694 reflections
b = 9.7536 (5) Åθ = 2.2–28.7°
c = 9.8471 (4) ŵ = 3.73 mm1
α = 76.273 (2)°T = 100 K
β = 74.240 (2)°Block, blue
γ = 85.024 (3)°0.41 × 0.38 × 0.35 mm
V = 691.86 (5) Å3
Data collection top
Bruker Kappa APEXII CCD area-detector
diffractometer
3515 independent reflections
Radiation source: fine-focus sealed tube3172 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.057
ϕ and ω scansθmax = 28.7°, θmin = 2.2°
Absorption correction: multi-scan
(SADABS; Bruker, 2005)
h = 1010
Tmin = 0.236, Tmax = 0.271k = 1213
11758 measured reflectionsl = 1313
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)] = 0.039Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.108H atoms treated by a mixture of independent and constrained refinement
S = 1.13 w = 1/[σ2(Fo2) + (0.0563P)2 + 0.169P]
where P = (Fo2 + 2Fc2)/3
3515 reflections(Δ/σ)max = 0.001
203 parametersΔρmax = 0.86 e Å3
0 restraintsΔρmin = 1.29 e Å3
Crystal data top
[Cu(C7H4BrO2)2(C6H6N2O)2(H2O)2]γ = 85.024 (3)°
Mr = 743.84V = 691.86 (5) Å3
Triclinic, P1Z = 1
a = 7.7072 (3) ÅMo Kα radiation
b = 9.7536 (5) ŵ = 3.73 mm1
c = 9.8471 (4) ÅT = 100 K
α = 76.273 (2)°0.41 × 0.38 × 0.35 mm
β = 74.240 (2)°
Data collection top
Bruker Kappa APEXII CCD area-detector
diffractometer
3515 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2005)
3172 reflections with I > 2σ(I)
Tmin = 0.236, Tmax = 0.271Rint = 0.057
11758 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0390 restraints
wR(F2) = 0.108H atoms treated by a mixture of independent and constrained refinement
S = 1.13Δρmax = 0.86 e Å3
3515 reflectionsΔρmin = 1.29 e Å3
203 parameters
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Br10.50803 (3)0.60173 (3)0.78887 (3)0.02585 (11)
Cu10.00000.00000.50000.00979 (12)
O10.1042 (2)0.17464 (16)0.50913 (16)0.0123 (3)
O20.1351 (2)0.26522 (18)0.64918 (17)0.0160 (3)
O30.4297 (2)0.00851 (18)0.84131 (16)0.0182 (4)
O40.3099 (2)0.0838 (2)0.43625 (18)0.0172 (4)
H410.271 (5)0.146 (4)0.402 (4)0.036 (9)*
H420.383 (5)0.042 (4)0.371 (4)0.043 (11)*
N10.0003 (2)0.08494 (19)0.70725 (18)0.0111 (4)
N20.3330 (3)0.1428 (2)1.0661 (2)0.0176 (4)
H210.251 (4)0.189 (3)1.134 (3)0.028 (10)*
H220.417 (4)0.110 (3)1.094 (3)0.016 (7)*
C10.0294 (3)0.2585 (2)0.5904 (2)0.0103 (4)
C20.1508 (3)0.3509 (2)0.6240 (2)0.0116 (4)
C30.0789 (3)0.4675 (2)0.6809 (2)0.0149 (4)
H30.04420.49430.68830.018*
C40.1860 (3)0.5448 (3)0.7267 (3)0.0174 (5)
H40.13750.62510.76440.021*
C50.3644 (3)0.5032 (2)0.7167 (2)0.0145 (4)
C60.4403 (3)0.3898 (2)0.6570 (2)0.0158 (5)
H60.56380.36380.64900.019*
C70.3328 (3)0.3151 (2)0.6094 (2)0.0144 (4)
H70.38370.23840.56630.017*
C80.1393 (3)0.1592 (2)0.8002 (2)0.0132 (4)
H80.24070.17210.76750.016*
C90.1386 (3)0.2178 (3)0.9430 (2)0.0170 (5)
H90.23820.27031.00720.020*
C100.0077 (3)0.1992 (2)0.9903 (2)0.0150 (4)
H100.01010.23881.08770.018*
C110.1524 (3)0.1221 (2)0.8948 (2)0.0109 (4)
C120.1421 (3)0.0671 (2)0.7527 (2)0.0122 (4)
H120.24050.01510.68590.015*
C130.3162 (3)0.0880 (2)0.9325 (2)0.0137 (5)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.02453 (18)0.03006 (18)0.03230 (18)0.00115 (12)0.01163 (13)0.01980 (13)
Cu10.0109 (2)0.0129 (2)0.00714 (19)0.00162 (14)0.00356 (14)0.00453 (14)
O10.0122 (7)0.0149 (8)0.0112 (7)0.0005 (6)0.0023 (6)0.0064 (6)
O20.0104 (8)0.0214 (9)0.0164 (8)0.0013 (6)0.0016 (6)0.0073 (6)
O30.0165 (8)0.0292 (9)0.0101 (7)0.0054 (7)0.0030 (6)0.0053 (7)
O40.0150 (8)0.0222 (9)0.0147 (8)0.0026 (7)0.0015 (7)0.0085 (7)
N10.0115 (9)0.0131 (9)0.0100 (8)0.0037 (7)0.0032 (7)0.0062 (7)
N20.0172 (10)0.0277 (11)0.0090 (9)0.0027 (9)0.0044 (8)0.0043 (8)
C10.0091 (9)0.0127 (10)0.0087 (9)0.0004 (7)0.0024 (8)0.0014 (8)
C20.0141 (10)0.0129 (10)0.0083 (9)0.0016 (8)0.0027 (8)0.0038 (8)
C30.0132 (10)0.0162 (11)0.0152 (10)0.0034 (8)0.0025 (8)0.0057 (9)
C40.0200 (12)0.0152 (11)0.0189 (11)0.0042 (9)0.0040 (9)0.0102 (9)
C50.0151 (11)0.0175 (11)0.0139 (10)0.0030 (8)0.0044 (8)0.0075 (8)
C60.0117 (10)0.0192 (11)0.0179 (10)0.0029 (8)0.0045 (9)0.0070 (9)
C70.0157 (11)0.0150 (11)0.0131 (10)0.0030 (8)0.0024 (8)0.0072 (8)
C80.0112 (10)0.0169 (11)0.0129 (10)0.0037 (8)0.0030 (8)0.0073 (8)
C90.0175 (12)0.0190 (11)0.0129 (10)0.0011 (9)0.0000 (9)0.0055 (9)
C100.0153 (11)0.0189 (11)0.0097 (9)0.0008 (9)0.0009 (8)0.0045 (8)
C110.0107 (10)0.0140 (10)0.0094 (9)0.0019 (8)0.0025 (8)0.0061 (8)
C120.0136 (10)0.0143 (10)0.0100 (9)0.0037 (8)0.0030 (8)0.0065 (8)
C130.0153 (11)0.0187 (11)0.0090 (10)0.0043 (9)0.0035 (8)0.0082 (8)
Geometric parameters (Å, º) top
Br1—C51.895 (2)C3—H30.9500
Cu1—O11.9756 (16)C4—C51.383 (3)
Cu1—O1i1.9756 (16)C4—H40.9500
Cu1—N12.0116 (16)C6—C51.386 (3)
Cu1—N1i2.0116 (16)C6—C71.384 (3)
Cu1—O42.4199 (16)C6—H60.9500
Cu1—O4i2.4199 (16)C7—H70.9500
O1—C11.272 (3)C8—N11.340 (3)
O2—C11.246 (3)C8—H80.9500
O3—C131.238 (3)C9—C81.388 (3)
O4—H410.87 (4)C9—H90.9500
O4—H420.79 (4)C10—C91.371 (3)
N2—C131.334 (3)C10—C111.391 (3)
N2—H210.85 (3)C10—H100.9500
N2—H220.88 (3)C11—C121.396 (3)
C1—C21.502 (3)C11—C131.493 (3)
C2—C71.393 (3)C12—N11.331 (3)
C3—C21.392 (3)C12—H120.9500
C3—C41.387 (3)
O1—Cu1—O1i180.0C4—C3—C2120.4 (2)
O1—Cu1—O485.01 (6)C4—C3—H3119.8
O1i—Cu1—O494.99 (6)C3—C4—H4120.5
O1—Cu1—O4i94.99 (6)C5—C4—C3119.0 (2)
O1i—Cu1—O4i85.01 (6)C5—C4—H4120.5
O1—Cu1—N190.51 (7)C4—C5—Br1119.31 (17)
O1i—Cu1—N189.49 (7)C4—C5—C6121.7 (2)
O1—Cu1—N1i89.49 (7)C6—C5—Br1119.02 (17)
O1i—Cu1—N1i90.51 (7)C5—C6—H6120.6
O4i—Cu1—O4180.0C7—C6—C5118.7 (2)
N1i—Cu1—N1180.0C7—C6—H6120.6
N1—Cu1—O486.82 (6)C2—C7—H7119.6
N1i—Cu1—O493.18 (6)C6—C7—C2120.8 (2)
N1—Cu1—O4i93.18 (6)C6—C7—H7119.6
N1i—Cu1—O4i86.82 (6)N1—C8—C9121.6 (2)
C1—O1—Cu1125.94 (15)N1—C8—H8119.2
Cu1—O4—H4187 (2)C9—C8—H8119.2
Cu1—O4—H42122 (3)C8—C9—H9120.4
H41—O4—H42105 (3)C10—C9—C8119.3 (2)
C8—N1—Cu1121.83 (14)C10—C9—H9120.4
C12—N1—Cu1118.84 (15)C9—C10—C11119.6 (2)
C12—N1—C8119.33 (18)C9—C10—H10120.2
C13—N2—H21124.3 (19)C11—C10—H10120.2
C13—N2—H22118.4 (19)C10—C11—C12117.8 (2)
H22—N2—H21115 (3)C10—C11—C13125.52 (19)
O1—C1—C2117.12 (18)C12—C11—C13116.7 (2)
O2—C1—O1125.2 (2)N1—C12—C11122.5 (2)
O2—C1—C2117.63 (19)N1—C12—H12118.8
C3—C2—C1119.91 (19)C11—C12—H12118.8
C3—C2—C7119.4 (2)O3—C13—N2122.1 (2)
C7—C2—C1120.53 (19)O3—C13—C11119.74 (18)
C2—C3—H3119.8N2—C13—C11118.2 (2)
O4—Cu1—O1—C1150.09 (16)C4—C3—C2—C71.9 (3)
O4i—Cu1—O1—C129.91 (16)C2—C3—C4—C50.8 (3)
N1—Cu1—O1—C163.33 (16)C3—C4—C5—Br1176.52 (17)
N1i—Cu1—O1—C1116.67 (16)C3—C4—C5—C62.5 (4)
O1—Cu1—N1—C1242.00 (15)C7—C6—C5—Br1177.63 (17)
O1i—Cu1—N1—C12138.00 (15)C7—C6—C5—C41.4 (4)
O1—Cu1—N1—C8138.32 (16)C5—C6—C7—C21.4 (3)
O1i—Cu1—N1—C841.68 (16)C9—C8—N1—Cu1179.86 (16)
O4—Cu1—N1—C1242.98 (15)C9—C8—N1—C120.2 (3)
O4i—Cu1—N1—C12137.02 (15)C10—C9—C8—N10.1 (3)
O4—Cu1—N1—C8136.71 (16)C11—C10—C9—C80.0 (3)
O4i—Cu1—N1—C843.29 (16)C9—C10—C11—C120.4 (3)
Cu1—O1—C1—O219.3 (3)C9—C10—C11—C13177.1 (2)
Cu1—O1—C1—C2157.31 (13)C10—C11—C12—N10.7 (3)
O1—C1—C2—C3164.19 (19)C13—C11—C12—N1177.08 (18)
O1—C1—C2—C720.9 (3)C10—C11—C13—O3174.0 (2)
O2—C1—C2—C319.0 (3)C10—C11—C13—N24.7 (3)
O2—C1—C2—C7156.0 (2)C12—C11—C13—O33.6 (3)
C1—C2—C7—C6171.9 (2)C12—C11—C13—N2177.76 (19)
C3—C2—C7—C63.0 (3)C11—C12—N1—Cu1179.75 (15)
C4—C3—C2—C1173.1 (2)C11—C12—N1—C80.6 (3)
Symmetry code: (i) x, y, z+1.
Hydrogen-bond geometry (Å, º) top
Cg is the centroid of the N1/C8–C12 pyridine ring.
D—H···AD—HH···AD···AD—H···A
N2—H21···O2ii0.85 (3)2.06 (3)2.831 (2)151 (3)
N2—H22···O3iii0.88 (3)2.03 (3)2.893 (3)166 (3)
O4—H41···O2i0.87 (4)1.86 (4)2.718 (2)167 (4)
O4—H42···O3iv0.78 (4)2.17 (4)2.911 (2)159 (4)
C6—H6···O2v0.952.433.377 (3)172
C4—H4···Cgvi0.952.633.581 (3)176
Symmetry codes: (i) x, y, z+1; (ii) x, y, z+2; (iii) x+1, y, z+2; (iv) x+1, y, z+1; (v) x+1, y, z; (vi) x, y+1, z.

Experimental details

Crystal data
Chemical formula[Cu(C7H4BrO2)2(C6H6N2O)2(H2O)2]
Mr743.84
Crystal system, space groupTriclinic, P1
Temperature (K)100
a, b, c (Å)7.7072 (3), 9.7536 (5), 9.8471 (4)
α, β, γ (°)76.273 (2), 74.240 (2), 85.024 (3)
V3)691.86 (5)
Z1
Radiation typeMo Kα
µ (mm1)3.73
Crystal size (mm)0.41 × 0.38 × 0.35
Data collection
DiffractometerBruker Kappa APEXII CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2005)
Tmin, Tmax0.236, 0.271
No. of measured, independent and
observed [I > 2σ(I)] reflections
11758, 3515, 3172
Rint0.057
(sin θ/λ)max1)0.677
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.039, 0.108, 1.13
No. of reflections3515
No. of parameters203
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.86, 1.29

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), Mercury (Macrae et al., 2006), WinGX publication routines (Farrugia, 1999) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top
Cg is the centroid of the N1/C8–C12 pyridine ring.
D—H···AD—HH···AD···AD—H···A
N2—H21···O2i0.85 (3)2.06 (3)2.831 (2)151 (3)
N2—H22···O3ii0.88 (3)2.03 (3)2.893 (3)166 (3)
O4—H41···O2iii0.87 (4)1.86 (4)2.718 (2)167 (4)
O4—H42···O3iv0.78 (4)2.17 (4)2.911 (2)159 (4)
C6—H6···O2v0.952.433.377 (3)172
C4—H4···Cgvi0.952.633.581 (3)176
Symmetry codes: (i) x, y, z+2; (ii) x+1, y, z+2; (iii) x, y, z+1; (iv) x+1, y, z+1; (v) x+1, y, z; (vi) x, y+1, z.
 

Acknowledgements

The authors are indebted to Anadolu University and the Medicinal Plants and Medicine Research Centre of Anadolu University, Eskişehir, Turkey, for the use of X-ray diffractometer. This work was supported financially by the Scientific and Technological Research Council of Turkey (grant No. 108 T657).

References

First citationAllen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19.  CrossRef Web of Science Google Scholar
First citationBigoli, F., Braibanti, A., Pellinghelli, M. A. & Tiripicchio, A. (1972). Acta Cryst. B28, 962–966.  CSD CrossRef CAS IUCr Journals Web of Science Google Scholar
First citationBruker (2005). SADABS. Bruker AXS Inc. Madison, Wisconsin, USA.  Google Scholar
First citationBruker (2007). APEX2 and SAINT. Bruker AXS Inc. Madison, Wisconsin, USA.  Google Scholar
First citationFarrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838.  CrossRef CAS IUCr Journals Google Scholar
First citationHökelek, T., Dal, H., Tercan, B., Özbek, F. E. & Necefoğlu, H. (2009a). Acta Cryst. E65, m466–m467.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationHökelek, T., Dal, H., Tercan, B., Özbek, F. E. & Necefoğlu, H. (2009b). Acta Cryst. E65, m607–m608.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationHökelek, T., Gündüz, H. & Necefoğlu, H. (1996). Acta Cryst. C52, 2470–2473.  CSD CrossRef Web of Science IUCr Journals Google Scholar
First citationHökelek, T. & Necefoğlu, H. (1998). Acta Cryst. C54, 1242–1244.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationHökelek, T. & Necefoğlu, H. (2007). Acta Cryst. E63, m821–m823.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationKrishnamachari, K. A. V. R. (1974). Am. J. Clin. Nutr. 27, 108–111.  CAS PubMed Web of Science Google Scholar
First citationMacrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453–457.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationNecefoğlu, H., Maracı, A., Özbek, F. E., Tercan, B. & Hökelek, T. (2011). Acta Cryst. E67, m619–m620.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 67| Part 7| July 2011| Pages m900-m901
Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds