Bis[2-(pyrrolidin-2-yl)-1H-benzimidazole-κ2N2,N3]copper(II) dinitrate dihydrate

Dai, J.

doi:10.1107/S160053680901808X

metal-organic compounds

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Volume 65| Part 6| June 2009| Page m661

doi:10.1107/S160053680901808X

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Bis[2-(pyrrolidin-2-yl)-1H-benzimidazole-κ²N²,N³]copper(II) dinitrate dihydrate

Jing Dai ^a ^*

^aOrdered Matter Science Research Center, College of Chemistry and Chemical Engineering, Southeast University, Nanjing 210096, People's Republic of China
^*Correspondence e-mail: fudavid88@yahoo.com.cn

(Received 3 April 2009; accepted 13 May 2009; online 20 May 2009)

In the title compound, [Cu(C₁₁H₁₃N₃)₂](NO₃)₂·2H₂O, synthesized by hydrothermal reaction of Cu(NO₃)₂ and racemic 2-(pyrrolidin-2-yl)-1H-1,3-benzimidazole, the Cu^II atom lies on an inversion centre. The distorted octahedral Cu^II environment contains two planar trans-related N,N-chelating 2-(pyrrolidin-2-yl)-1H-1,3-benzimidazole ligands in the equatorial plane and two monodentate nitrate anions, which are in weak interaction with the Cu atom, in the axial positions. The two benzimidazole ligands have opposite configurations (R/S and S/R) and compound is a meso complex. In the crystal, N—H⋯O and O—H⋯O hydrogen bonds generate an infinite three-dimensional network. One methylene group of the pyrrolidine ring is disordered over two position with a 0.56 (3):0.44 (3) occupancy.

Related literature

For physical properties such as the ferroelectric and dielectric behavior of metal-organic coordination compounds, see: Fu et al. (2007 ). For the synthesis, see: Aminabhavi et al. (1986 ). For related structures, see: Dai & Fu (2008a ,b ); Fu & Ye (2007 ).

Experimental

Crystal data

[Cu(C₁₁H₁₃N₃)₂](NO₃)₂·2H₂O
M_r = 598.08
Triclinic, $[P \overline 1]$
a = 8.2790 (17) Å
b = 8.4446 (17) Å
c = 9.759 (2) Å
α = 100.37 (3)°
β = 107.15 (3)°
γ = 91.37 (3)°
V = 639.1 (2) Å³
Z = 1
Mo Kα radiation
μ = 0.92 mm⁻¹
T = 298 K
0.35 × 0.30 × 0.15 mm

Data collection

Rigaku Mercury2 diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ) T_min = 0.732, T_max = 0.871
6713 measured reflections
2914 independent reflections
2566 reflections with I > 2σ(I)
R_int = 0.027

Refinement

R[F² > 2σ(F²)] = 0.043
wR(F²) = 0.101
S = 1.11
2914 reflections
188 parameters
6 restraints
H-atom parameters constrained
Δρ_max = 0.33 e Å⁻³
Δρ_min = −0.31 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3B⋯O1ⁱ	0.91	2.25	2.986 (3)	137
O1W—H1WA⋯O2ⁱⁱ	0.93	1.92	2.836 (4)	169
O1W—H1WB⋯O2ⁱⁱⁱ	0.98	1.94	2.861 (3)	155
N2—H2B⋯O1W	0.86	1.86	2.706 (3)	168
Symmetry codes: (i) -x+2, -y+1, -z+1; (ii) -x+1, -y+1, -z+1; (iii) x, y+1, z+1.

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear; data reduction: CrystalClear; 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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053680901808X/dn2443sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053680901808X/dn2443Isup2.hkl

checkCIF report

Comment top

Amino acid derivatives have found wide range of applications in material science, such as ferroelectric, fluorescence and dielectric behaviors. And there has been an increased interest in the preparation of amino acid coordination compound (Aminabhavi et al., 1986; Dai & Fu 2008a; Fu & Ye 2007; Dai & Fu 2008b; Fu, et al. 2007). We report here the crystal structure of the title compound, [Nitrate-[2-(pyrrolidin-2-yl)-1H-benzimidazole] Copper(II)] dihydrate.

In the title compound, the Cu^II atom lies on an inversion centre. The distorted octahedral Cu^II environment contains two planar trans-related N,N-chelating 2-(pyrrolidin-2-yl)-1H-1,3-benzimidazole ligands in the equatorial plane and two monodentate nitrate anion ligands which are in weak interaction with the Cu atom in the axial position. The two benzimidazole ligands have opposite configuration R,S and S,R and the complex is meso(Fig. 1).

In the crystal structure, molecules are linked into a three-dimension network by N—H···O and O—H···O hydrogen bonds.(Fig.2, Table 1).

Related literature top

For physical properties such as the ferroelectric and dielectric behavior of metal-organic coordination compounds, see: Fu et al. (2007). For the synthesis, see: Aminabhavi et al. (1986). For related structures, see: Dai & Fu (2008a,b); Fu & Ye (2007).

Experimental top

The racemic ligand 2-(pyrrolidin-2-yl)-1H-benzo[d]imidazole was synthesized by reaction of S-pyrrolidine-2-carboxylic acid and benzene-1,2-diamine according to the procedure described in the literature(Aminabhavi, et al.(1986)). A mixture of 2-(pyrrolidin-2-yl)-1H-benzo[d]imidazole (0.1 mmol) and Cu(NO₃)₂ (0.1 mmol) and water (1 ml) sealed in a glass tube were maintained at 70 °C. Crystals suitable for X-ray analysis were obtained after 5 days.

Computing details top

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear (Rigaku, 2005); data reduction: CrystalClear (Rigaku, 2005); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. A view of the title compound with the atomic numbering scheme. Displacement ellipsoids were drawn at the 30% probability level. H atoms have been omitted. The weak interaction of Cu^II with nitrate is shown.
	Fig. 2. The crystal packing of the title compound viewed along the a axis and all hydrogen atoms not involved in hydrogen bonding (dashed lines) were omitted for clarity.

Bis[2-(pyrrolidin-2-yl)-1H-benzimidazole- κ²N²,N³]copper(II) dinitrate dihydrate top

Crystal data top

[Cu(C₁₁H₁₃N₃)₂](NO₃)₂·2H₂O	Z = 1
M_r = 598.08	F(000) = 311
Triclinic, P1	D_x = 1.554 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.2790 (17) Å	Cell parameters from 2913 reflections
b = 8.4446 (17) Å	θ = 3.4–27.5°
c = 9.759 (2) Å	µ = 0.92 mm⁻¹
α = 100.37 (3)°	T = 298 K
β = 107.15 (3)°	Block, blue
γ = 91.37 (3)°	0.35 × 0.30 × 0.15 mm
V = 639.1 (2) Å³

Data collection top

Rigaku Mercury2 diffractometer	2914 independent reflections
Radiation source: fine-focus sealed tube	2566 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.027
Detector resolution: 13.6612 pixels mm^-1	θ_max = 27.5°, θ_min = 3.4°
CCD profile fitting scans	h = −10→10
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −10→10
T_min = 0.732, T_max = 0.871	l = −12→12
6713 measured reflections

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.101	H-atom parameters constrained
S = 1.11	w = 1/[σ²(F_o²) + (0.0352P)² + 0.444P] where P = (F_o² + 2F_c²)/3
2914 reflections	(Δ/σ)_max < 0.001
188 parameters	Δρ_max = 0.33 e Å⁻³
6 restraints	Δρ_min = −0.31 e Å⁻³

Crystal data top

[Cu(C₁₁H₁₃N₃)₂](NO₃)₂·2H₂O	γ = 91.37 (3)°
M_r = 598.08	V = 639.1 (2) Å³
Triclinic, P1	Z = 1
a = 8.2790 (17) Å	Mo Kα radiation
b = 8.4446 (17) Å	µ = 0.92 mm⁻¹
c = 9.759 (2) Å	T = 298 K
α = 100.37 (3)°	0.35 × 0.30 × 0.15 mm
β = 107.15 (3)°

Data collection top

Rigaku Mercury2 diffractometer	2914 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	2566 reflections with I > 2σ(I)
T_min = 0.732, T_max = 0.871	R_int = 0.027
6713 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.043	6 restraints
wR(F²) = 0.101	H-atom parameters constrained
S = 1.11	Δρ_max = 0.33 e Å⁻³
2914 reflections	Δρ_min = −0.31 e Å⁻³
188 parameters

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.

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
Cu1	1.0000	0.5000	0.5000	0.03289 (14)
O1	0.8537 (3)	0.0645 (3)	0.4119 (3)	0.0643 (6)
O2	0.6487 (3)	0.0360 (3)	0.2118 (3)	0.0745 (7)
O3	0.7605 (3)	0.2727 (3)	0.3222 (3)	0.0647 (6)
N1	0.9102 (2)	0.4814 (2)	0.6652 (2)	0.0329 (4)
N2	0.7676 (3)	0.5950 (3)	0.8117 (2)	0.0406 (5)
H2B	0.7115	0.6647	0.8502	0.049*
N3	0.8509 (3)	0.6877 (2)	0.4834 (2)	0.0345 (4)
H3B	0.9103	0.7701	0.4663	0.041*
N4	0.7551 (3)	0.1246 (3)	0.3161 (2)	0.0425 (5)
C1	0.8109 (3)	0.4496 (3)	0.8525 (3)	0.0383 (6)
C2	0.7753 (4)	0.3760 (4)	0.9580 (3)	0.0507 (7)
H2A	0.7151	0.4256	1.0184	0.061*
C3	0.8337 (4)	0.2263 (4)	0.9686 (3)	0.0552 (8)
H3A	0.8115	0.1721	1.0369	0.066*
C4	0.9250 (4)	0.1551 (4)	0.8794 (3)	0.0564 (8)
H4A	0.9643	0.0545	0.8909	0.068*
C5	0.9603 (4)	0.2272 (3)	0.7737 (3)	0.0467 (6)
H5A	1.0208	0.1769	0.7139	0.056*
C6	0.9014 (3)	0.3778 (3)	0.7609 (2)	0.0348 (5)
C7	0.8291 (3)	0.6078 (3)	0.7009 (3)	0.0338 (5)
C8	0.8131 (3)	0.7461 (3)	0.6234 (3)	0.0380 (6)
H8A	0.8966	0.8350	0.6830	0.046*
C9	0.6378 (4)	0.8083 (5)	0.5821 (4)	0.0658 (9)
H9A	0.5789	0.7940	0.6520	0.079*
H9B	0.6446	0.9216	0.5764	0.079*
C11	0.6832 (4)	0.6571 (4)	0.3660 (3)	0.0542 (8)
H11A	0.6811	0.7192	0.2911	0.065*
H11B	0.6610	0.5435	0.3209	0.065*
O1W	0.5901 (3)	0.7856 (3)	0.9583 (3)	0.0757 (7)
H1WA	0.5045	0.8317	0.8968	0.113*
H1WB	0.6169	0.8451	1.0596	0.113*
C10	0.5552 (12)	0.709 (2)	0.4410 (13)	0.066 (3)	0.56 (3)
H10A	0.4736	0.7698	0.3822	0.079*	0.56 (3)
H10B	0.4948	0.6151	0.4524	0.079*	0.56 (3)
C10'	0.5655 (18)	0.773 (2)	0.4195 (16)	0.055 (3)	0.44 (3)
H10C	0.5642	0.8711	0.3809	0.066*	0.44 (3)
H10D	0.4507	0.7226	0.3896	0.066*	0.44 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.0347 (2)	0.0409 (3)	0.0285 (2)	0.01231 (17)	0.01597 (17)	0.00874 (17)
O1	0.0575 (13)	0.0570 (13)	0.0686 (14)	0.0016 (10)	−0.0016 (11)	0.0231 (11)
O2	0.0782 (16)	0.0615 (14)	0.0594 (14)	0.0032 (12)	−0.0028 (13)	−0.0098 (11)
O3	0.0681 (15)	0.0449 (12)	0.0709 (15)	0.0090 (10)	0.0053 (12)	0.0119 (11)
N1	0.0356 (10)	0.0360 (10)	0.0300 (10)	0.0063 (8)	0.0148 (8)	0.0052 (8)
N2	0.0427 (12)	0.0473 (12)	0.0368 (11)	0.0108 (10)	0.0227 (10)	0.0027 (9)
N3	0.0368 (11)	0.0351 (10)	0.0355 (11)	0.0066 (8)	0.0161 (9)	0.0077 (8)
N4	0.0372 (12)	0.0490 (13)	0.0411 (12)	0.0057 (10)	0.0151 (10)	0.0025 (10)
C1	0.0386 (13)	0.0454 (14)	0.0311 (12)	−0.0013 (11)	0.0142 (10)	0.0025 (10)
C2	0.0549 (17)	0.0651 (19)	0.0374 (14)	−0.0001 (14)	0.0250 (13)	0.0056 (13)
C3	0.075 (2)	0.0581 (18)	0.0381 (15)	−0.0063 (16)	0.0241 (14)	0.0133 (13)
C4	0.085 (2)	0.0457 (16)	0.0441 (16)	0.0056 (15)	0.0246 (16)	0.0150 (13)
C5	0.0660 (18)	0.0421 (15)	0.0378 (14)	0.0090 (13)	0.0244 (13)	0.0076 (11)
C6	0.0401 (13)	0.0387 (13)	0.0257 (11)	0.0003 (10)	0.0127 (10)	0.0024 (10)
C7	0.0313 (12)	0.0393 (13)	0.0306 (12)	0.0026 (10)	0.0120 (10)	0.0016 (10)
C8	0.0420 (14)	0.0362 (13)	0.0383 (13)	0.0094 (11)	0.0177 (11)	0.0033 (10)
C9	0.064 (2)	0.081 (2)	0.071 (2)	0.0437 (18)	0.0356 (18)	0.0315 (19)
C11	0.0545 (18)	0.0480 (16)	0.0471 (16)	0.0155 (13)	−0.0014 (14)	0.0035 (13)
O1W	0.0743 (16)	0.0971 (18)	0.0527 (13)	0.0449 (14)	0.0207 (12)	0.0000 (12)
C10	0.036 (3)	0.071 (7)	0.086 (5)	0.000 (4)	0.003 (3)	0.032 (5)
C10'	0.041 (5)	0.049 (7)	0.071 (6)	0.018 (5)	0.012 (4)	0.009 (5)

Geometric parameters (Å, º) top

Cu1—N1ⁱ	1.9922 (19)	C4—C5	1.384 (4)
Cu1—N1	1.9922 (19)	C4—H4A	0.9300
Cu1—N3	2.032 (2)	C5—C6	1.386 (4)
Cu1—N3ⁱ	2.032 (2)	C5—H5A	0.9300
O1—N4	1.241 (3)	C7—C8	1.490 (3)
O2—N4	1.240 (3)	C8—C9	1.520 (4)
O3—N4	1.241 (3)	C8—H8A	0.9800
N1—C7	1.324 (3)	C9—C10	1.438 (13)
N1—C6	1.405 (3)	C9—C10'	1.492 (15)
N2—C7	1.343 (3)	C9—H9A	0.9700
N2—C1	1.382 (3)	C9—H9B	0.9700
N2—H2B	0.8600	C11—C10	1.488 (12)
N3—C8	1.491 (3)	C11—C10'	1.529 (11)
N3—C11	1.499 (3)	C11—H11A	0.9700
N3—H3B	0.9100	C11—H11B	0.9700
C1—C2	1.391 (4)	O1W—H1WA	0.9281
C1—C6	1.397 (3)	O1W—H1WB	0.9827
C2—C3	1.375 (4)	C10—H10A	0.9700
C2—H2A	0.9300	C10—H10B	0.9700
C3—C4	1.383 (4)	C10'—H10C	0.9700
C3—H3A	0.9300	C10'—H10D	0.9700

N1ⁱ—Cu1—N1	180.000 (1)	N1—C7—C8	121.5 (2)
N1ⁱ—Cu1—N3	97.34 (8)	N2—C7—C8	126.0 (2)
N1—Cu1—N3	82.66 (8)	C7—C8—N3	106.82 (19)
N1ⁱ—Cu1—N3ⁱ	82.66 (8)	C7—C8—C9	115.3 (2)
N1—Cu1—N3ⁱ	97.34 (8)	N3—C8—C9	106.4 (2)
N3—Cu1—N3ⁱ	180.00 (12)	C7—C8—H8A	109.4
C7—N1—C6	105.71 (19)	N3—C8—H8A	109.4
C7—N1—Cu1	112.43 (16)	C9—C8—H8A	109.4
C6—N1—Cu1	141.85 (16)	C10—C9—C8	102.8 (6)
C7—N2—C1	107.5 (2)	C10'—C9—C8	108.6 (5)
C7—N2—H2B	126.2	C10—C9—H9A	111.2
C1—N2—H2B	126.2	C10'—C9—H9A	126.7
C8—N3—C11	106.2 (2)	C8—C9—H9A	111.2
C8—N3—Cu1	110.88 (15)	C10—C9—H9B	111.2
C11—N3—Cu1	116.78 (16)	C10'—C9—H9B	87.2
C8—N3—H3B	107.5	C8—C9—H9B	111.2
C11—N3—H3B	107.5	H9A—C9—H9B	109.1
Cu1—N3—H3B	107.5	C10—C11—N3	105.4 (5)
O2—N4—O3	118.9 (2)	N3—C11—C10'	106.2 (5)
O2—N4—O1	119.9 (2)	C10—C11—H11A	110.7
O3—N4—O1	121.2 (2)	N3—C11—H11A	110.7
N2—C1—C2	131.1 (2)	C10'—C11—H11A	88.8
N2—C1—C6	106.1 (2)	C10—C11—H11B	110.7
C2—C1—C6	122.8 (3)	N3—C11—H11B	110.7
C3—C2—C1	116.6 (3)	C10'—C11—H11B	129.2
C3—C2—H2A	121.7	H11A—C11—H11B	108.8
C1—C2—H2A	121.7	H1WA—O1W—H1WB	110.4
C2—C3—C4	121.0 (3)	C9—C10—C11	109.9 (6)
C2—C3—H3A	119.5	C9—C10—H10A	109.7
C4—C3—H3A	119.5	C11—C10—H10A	109.7
C3—C4—C5	122.7 (3)	C9—C10—H10B	109.7
C3—C4—H4A	118.7	C11—C10—H10B	109.7
C5—C4—H4A	118.7	H10A—C10—H10B	108.2
C4—C5—C6	117.1 (3)	C9—C10'—C11	104.9 (8)
C4—C5—H5A	121.5	C9—C10'—H10C	110.8
C6—C5—H5A	121.5	C11—C10'—H10C	110.8
C5—C6—C1	119.8 (2)	C9—C10'—H10D	110.8
C5—C6—N1	132.0 (2)	C11—C10'—H10D	110.8
C1—C6—N1	108.1 (2)	H10C—C10'—H10D	108.8
N1—C7—N2	112.5 (2)

N3—Cu1—N1—C7	−11.34 (17)	Cu1—N1—C7—C8	−0.8 (3)
N3ⁱ—Cu1—N1—C7	168.66 (17)	C1—N2—C7—N1	−0.1 (3)
N3—Cu1—N1—C6	168.4 (3)	C1—N2—C7—C8	−179.6 (2)
N3ⁱ—Cu1—N1—C6	−11.6 (3)	N1—C7—C8—N3	17.5 (3)
N1ⁱ—Cu1—N3—C8	−159.18 (16)	N2—C7—C8—N3	−163.0 (2)
N1—Cu1—N3—C8	20.82 (16)	N1—C7—C8—C9	135.5 (3)
N1ⁱ—Cu1—N3—C11	79.0 (2)	N2—C7—C8—C9	−45.1 (4)
N1—Cu1—N3—C11	−101.0 (2)	C11—N3—C8—C7	102.9 (2)
C7—N2—C1—C2	−178.2 (3)	Cu1—N3—C8—C7	−24.9 (2)
C7—N2—C1—C6	0.3 (3)	C11—N3—C8—C9	−20.7 (3)
N2—C1—C2—C3	178.1 (3)	Cu1—N3—C8—C9	−148.6 (2)
C6—C1—C2—C3	−0.2 (4)	C7—C8—C9—C10	−88.1 (7)
C1—C2—C3—C4	0.8 (5)	N3—C8—C9—C10	30.0 (7)
C2—C3—C4—C5	−1.2 (5)	C7—C8—C9—C10'	−112.9 (9)
C3—C4—C5—C6	0.7 (5)	N3—C8—C9—C10'	5.3 (10)
C4—C5—C6—C1	−0.1 (4)	C8—N3—C11—C10	3.6 (8)
C4—C5—C6—N1	−178.1 (3)	Cu1—N3—C11—C10	127.8 (7)
N2—C1—C6—C5	−178.9 (2)	C8—N3—C11—C10'	28.3 (10)
C2—C1—C6—C5	−0.2 (4)	Cu1—N3—C11—C10'	152.6 (9)
N2—C1—C6—N1	−0.4 (3)	C10'—C9—C10—C11	78.5 (18)
C2—C1—C6—N1	178.3 (2)	C8—C9—C10—C11	−28.4 (12)
C7—N1—C6—C5	178.6 (3)	N3—C11—C10—C9	16.2 (12)
Cu1—N1—C6—C5	−1.1 (5)	C10'—C11—C10—C9	−79 (2)
C7—N1—C6—C1	0.4 (3)	C10—C9—C10'—C11	−68.1 (16)
Cu1—N1—C6—C1	−179.4 (2)	C8—C9—C10'—C11	11.8 (14)
C6—N1—C7—N2	−0.2 (3)	C10—C11—C10'—C9	67 (2)
Cu1—N1—C7—N2	179.63 (16)	N3—C11—C10'—C9	−24.6 (14)
C6—N1—C7—C8	179.4 (2)

Symmetry code: (i) −x+2, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3B···O1ⁱ	0.91	2.25	2.986 (3)	137
O1W—H1WA···O2ⁱⁱ	0.93	1.92	2.836 (4)	169
O1W—H1WB···O2ⁱⁱⁱ	0.98	1.94	2.861 (3)	155
N2—H2B···O1W	0.86	1.86	2.706 (3)	168

Symmetry codes: (i) −x+2, −y+1, −z+1; (ii) −x+1, −y+1, −z+1; (iii) x, y+1, z+1.

Experimental details

Crystal data
Chemical formula	[Cu(C₁₁H₁₃N₃)₂](NO₃)₂·2H₂O
M_r	598.08
Crystal system, space group	Triclinic, P1
Temperature (K)	298
a, b, c (Å)	8.2790 (17), 8.4446 (17), 9.759 (2)
α, β, γ (°)	100.37 (3), 107.15 (3), 91.37 (3)
V (Å³)	639.1 (2)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	0.92
Crystal size (mm)	0.35 × 0.30 × 0.15

Data collection
Diffractometer	Rigaku Mercury2 diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku, 2005)
T_min, T_max	0.732, 0.871
No. of measured, independent and observed [I > 2σ(I)] reflections	6713, 2914, 2566
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.043, 0.101, 1.11
No. of reflections	2914
No. of parameters	188
No. of restraints	6
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.33, −0.31

Computer programs: CrystalClear (Rigaku, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3B···O1ⁱ	0.91	2.25	2.986 (3)	137.1
O1W—H1WA···O2ⁱⁱ	0.93	1.92	2.836 (4)	169.4
O1W—H1WB···O2ⁱⁱⁱ	0.98	1.94	2.861 (3)	155.2
N2—H2B···O1W	0.86	1.86	2.706 (3)	168.3

Symmetry codes: (i) −x+2, −y+1, −z+1; (ii) −x+1, −y+1, −z+1; (iii) x, y+1, z+1.

Acknowledgements

This work was supported by a Start-up Grant from Southeast University to Professor Ren-Gen Xiong.

References

Aminabhavi, T. M., Biradar, N. S. & Patil, S. B. (1986). Inorg. Chim. Acta, 125, 125–128. CrossRef CAS Web of Science Google Scholar
Dai, W. & Fu, D.-W. (2008a). Acta Cryst. E64, m1016. Web of Science CSD CrossRef IUCr Journals Google Scholar
Dai, W. & Fu, D.-W. (2008b). Acta Cryst. E64, m1017. Web of Science CSD CrossRef IUCr Journals Google Scholar
Fu, D.-W., Song, Y.-M., Wang, G.-X., Ye, Q. & Xiong, R.-G. (2007). J. Am. Chem. Soc. 129, 5346–5347. Web of Science CSD CrossRef PubMed CAS Google Scholar
Fu, D.-W. & Ye, H.-Y. (2007). Acta Cryst. E63, m2453. Web of Science CSD CrossRef IUCr Journals Google Scholar
Rigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar