Bis[1,3-bis­(benzimidazol-2-yl)-2-oxapropane]copper(II)–picrate–dimethyl­formamide (1/2/4)

Yun, R.; Ying, W.; Qi, B.; Fan, X.; Wu, H.

doi:10.1107/S1600536808036829

metal-organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 64| Part 12| December 2008| Page m1529

doi:10.1107/S1600536808036829

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Bis[1,3-bis(benzimidazol-2-yl)-2-oxapropane]copper(II)–picrate–dimethylformamide (1/2/4)

Ruirui Yun,^a Wei Ying,^b Baoliang Qi,^a Xuyang Fan ^a and Huilu Wu ^a ^*

^aSchool of Chemical and Biological Engineering, Lanzhou Jiaotong University, Lanzhou 730070, People's Republic of China, and ^bCollege of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000, People's Republic of China
^*Correspondence e-mail: wuhuilu@163.com

(Received 18 October 2008; accepted 8 November 2008; online 13 November 2008)

In the title compound, [Cu(C₁₆H₁₄N₄O)₂](C₆H₂N₃O₇)₂·4C₃H₇NO, the Cu^II ion is located on a crystallographic inversion center and is coordinated in a distorted octahedral environment by four N atoms and two O atoms forming two long Cu—O bonds. One of the unique dimethylformamide solvent molecules is disordered over two sites with occupancies of 0.715 (6) and 0.285 (6). The crystal structure is stabilized by intermolecular N—H⋯O hydrogen bonds.

Related literature

For the analagous Zn(II) diperchlorate complex, see: Zhou & Yang (2006 ).

Experimental

Crystal data

[Cu(C₁₆H₁₄N₄O)₂](C₆H₂N₃O₇)₂·4C₃H₇NO
M_r = 1368.77
Triclinic, $[P \overline 1]$
a = 10.9656 (7) Å
b = 12.6028 (12) Å
c = 13.4100 (9) Å
α = 65.746 (2)°
β = 88.629 (2)°
γ = 65.187 (2)°
V = 1508.8 (2) Å³
Z = 1
Mo Kα radiation
μ = 0.46 mm⁻¹
T = 293 (2) K
0.28 × 0.21 × 0.11 mm

Data collection

Rigaku R-AXIS Spider diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ) T_min = 0.883, T_max = 0.952
12429 measured reflections
5605 independent reflections
3363 reflections with I > 2σ(I)
R_int = 0.078

Refinement

R[F² > 2σ(F²)] = 0.075
wR(F²) = 0.232
S = 1.01
5605 reflections
457 parameters
18 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.78 e Å⁻³
Δρ_min = −1.09 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

Cu—N3	1.979 (3)
Cu—N1	1.992 (4)
Cu—O1	2.583 (3)

N3—Cu—N3ⁱ	180
N3—Cu—N1	87.55 (15)
N3—Cu—N1ⁱ	92.45 (15)
N1—Cu—N1ⁱ	180
N3—Cu—O1ⁱ	106.54 (12)
N1—Cu—O1ⁱ	106.14 (13)
N3—Cu—O1	73.46 (12)
N1—Cu—O1	73.86 (13)
O1ⁱ—Cu—O1	180
Symmetry code: (i) -x, -y+1, -z+1.

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2N⋯O6ⁱⁱ	0.87 (5)	1.95 (4)	2.709 (5)	145 (6)
N2—H2N⋯O5ⁱⁱ	0.87 (5)	2.41 (5)	3.104 (6)	138 (6)
N4—H4N⋯O9ⁱⁱⁱ	0.87 (5)	1.92 (2)	2.753 (6)	162 (5)
Symmetry codes: (ii) -x+1, -y, -z+2; (iii) -x+1, -y+1, -z+1.

Data collection: RAPID-AUTO (Rigaku/MSC, 2004 ); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2003 ); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808036829/lh2715sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808036829/lh2715Isup2.hkl

checkCIF report

Comment top

The asymmetric unit of the title compound consists of half of a di[1,3-bis(benzimidazol-2-yl)-2-oxopropane] copper(II) cation (Fig.1), one picrate anion and two molecules of DMF. The Cu^II ion is six-coordinated with a N₄O₂ ligand set. The obb (1,3-bis(benzimidazol-2-yl)-2-oxopropane) ligand acts as a tridentate donor. The coordination geometry of the Cu^II may be best described as distorted octahedral. This geometry is assumed by the Cu^II to relieve the steric crowding. The equatorial plane is occupied by four N atoms of two benzimidazolyl groups. The axial positions are occuppied two O atoms. The crystal structure is stabilized by intermolecular N-H···O hydrogen bonds.

Related literature top

For the analagous Zn(II) diperchlorate complex, see: Zhou & Yang (2006).

Experimental top

To a stirred solution of 1,3-bis(benzimidazol-2-yl)-2-oxopropane (0.139 g, 0.5 mmol) in hot MeOH (15 ml) was added Cu(C₆H₂N₃O₇)₂ (0.130 g, 0.25 mmol) in MeOH (5 ml). A green crystalline product formed rapidly. The precipitate was filtered off, washed with MeOH and absolute Et₂O, and dried in vacuo. The dried precipitate was dissolved in DMF resulting in a green solution. The green crystals suitable for X-ray diffraction studies were obtained by ether diffusion into DMF after three days at room temperature. Yield, 0.106 g (66%). (found: C, 49.23; H, 4.37; N,18.58. Calcd. for C56H60N18O20Cu: C, 49.14; H, 4.42; N, 18.42)

Computing details top

Data collection: RAPID-AUTO (Rigaku/MSC, 2004); cell refinement: RAPID-AUTO (Rigaku/MSC, 2004); data reduction: RAPID-AUTO (Rigaku/MSC, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. The cation of the title compound showing displacement ellipsoids at the 30% probability level [symmetry code: (a) -x, -y+1, -x+1].

Bis[1,3-bis(benzimidazol-2-yl)-2-oxapropane]copper(II)–picrate–dimethylformamide (1/2/4) top

Crystal data top

[Cu(C₁₆H₁₄N₄O)₂](C₆H₂N₃O₇)₂·4C₃H₇NO	Z = 1
M_r = 1368.77	F(000) = 711
Triclinic, P1	D_x = 1.506 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.9656 (7) Å	Cell parameters from 5605 reflections
b = 12.6028 (12) Å	θ = 3.0–25.5°
c = 13.4100 (9) Å	µ = 0.46 mm⁻¹
α = 65.746 (2)°	T = 293 K
β = 88.629 (2)°	Block, green
γ = 65.187 (2)°	0.28 × 0.21 × 0.11 mm
V = 1508.8 (2) Å³

Data collection top

Rigaku R-AXIS Spider diffractometer	5605 independent reflections
Radiation source: fine-focus sealed tube	3363 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.078
ϕ and ω scans	θ_max = 25.5°, θ_min = 3.0°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −13→13
T_min = 0.883, T_max = 0.952	k = −15→15
12429 measured reflections	l = −16→15

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.075	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.232	w = 1/[σ²(F_o²) + (0.1327P)²] where P = (F_o² + 2F_c²)/3
S = 1.02	(Δ/σ)_max < 0.001
5605 reflections	Δρ_max = 0.78 e Å⁻³
457 parameters	Δρ_min = −1.09 e Å⁻³
18 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.009 (3)

Crystal data top

[Cu(C₁₆H₁₄N₄O)₂](C₆H₂N₃O₇)₂·4C₃H₇NO	γ = 65.187 (2)°
M_r = 1368.77	V = 1508.8 (2) Å³
Triclinic, P1	Z = 1
a = 10.9656 (7) Å	Mo Kα radiation
b = 12.6028 (12) Å	µ = 0.46 mm⁻¹
c = 13.4100 (9) Å	T = 293 K
α = 65.746 (2)°	0.28 × 0.21 × 0.11 mm
β = 88.629 (2)°

Data collection top

Rigaku R-AXIS Spider diffractometer	5605 independent reflections
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	3363 reflections with I > 2σ(I)
T_min = 0.883, T_max = 0.952	R_int = 0.078
12429 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.075	18 restraints
wR(F²) = 0.232	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	Δρ_max = 0.78 e Å⁻³
5605 reflections	Δρ_min = −1.09 e Å⁻³
457 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)
Cu	0.0000	0.5000	0.5000	0.0414 (3)
O1	0.1409 (3)	0.5704 (3)	0.5882 (2)	0.0445 (8)
O2	−0.1106 (4)	0.1849 (4)	0.7815 (3)	0.0747 (12)
O3	−0.0335 (4)	−0.0186 (5)	0.8206 (3)	0.0701 (11)
O4	0.4289 (4)	−0.3097 (4)	1.0041 (3)	0.0651 (11)
O5	0.4919 (4)	−0.2964 (4)	1.1479 (3)	0.0816 (14)
O6	0.4312 (3)	−0.0496 (4)	1.1048 (3)	0.0577 (10)
O7	0.3068 (6)	0.1965 (6)	1.0630 (6)	0.151 (3)
O8	0.1451 (5)	0.3258 (4)	0.9307 (4)	0.0838 (13)
N1	0.1462 (3)	0.3364 (4)	0.6167 (3)	0.0418 (9)
N2	0.3339 (4)	0.2162 (4)	0.7450 (3)	0.0440 (10)
N3	0.1426 (3)	0.5132 (4)	0.4093 (3)	0.0434 (10)
N4	0.3198 (4)	0.5527 (5)	0.3577 (3)	0.0493 (10)
N5	−0.0233 (4)	0.0710 (6)	0.8286 (3)	0.0577 (12)
N6	0.4176 (4)	−0.2487 (5)	1.0584 (3)	0.0574 (12)
N7	0.2262 (4)	0.2166 (5)	0.9921 (3)	0.0593 (12)
C1	0.1934 (4)	0.2071 (5)	0.6375 (4)	0.0431 (11)
C2	0.1446 (5)	0.1495 (5)	0.5898 (4)	0.0488 (12)
H2	0.0674	0.1994	0.5343	0.059*
C3	0.2141 (5)	0.0169 (6)	0.6273 (4)	0.0561 (13)
H3	0.1823	−0.0239	0.5980	0.067*
C4	0.3320 (5)	−0.0576 (6)	0.7088 (4)	0.0586 (14)
H4	0.3773	−0.1471	0.7319	0.070*
C5	0.3832 (5)	−0.0029 (5)	0.7558 (4)	0.0490 (12)
H5	0.4619	−0.0528	0.8098	0.059*
C6	0.3118 (4)	0.1294 (5)	0.7189 (3)	0.0436 (11)
C7	0.2347 (4)	0.3364 (5)	0.6822 (4)	0.0433 (12)
C8	0.2230 (4)	0.4562 (5)	0.6871 (4)	0.0468 (12)
H8A	0.1828	0.4627	0.7508	0.056*
H8B	0.3134	0.4503	0.6965	0.056*
C9	0.2173 (4)	0.6123 (5)	0.5063 (4)	0.0481 (12)
H9A	0.3083	0.5841	0.5424	0.058*
H9B	0.1733	0.7067	0.4674	0.058*
C10	0.2273 (4)	0.5579 (5)	0.4249 (4)	0.0464 (12)
C11	0.2956 (4)	0.5003 (5)	0.2916 (4)	0.0498 (13)
C12	0.3633 (5)	0.4699 (6)	0.2106 (4)	0.0596 (15)
H12	0.4351	0.4895	0.1874	0.072*
C13	0.3170 (5)	0.4088 (7)	0.1670 (5)	0.0686 (17)
H13	0.3598	0.3854	0.1134	0.082*
C14	0.2084 (5)	0.3810 (6)	0.2004 (4)	0.0662 (16)
H14	0.1808	0.3396	0.1687	0.079*
C15	0.1411 (5)	0.4134 (6)	0.2791 (4)	0.0564 (14)
H15	0.0686	0.3947	0.3014	0.068*
C16	0.1863 (4)	0.4754 (5)	0.3240 (4)	0.0444 (11)
C17	0.0969 (4)	0.0407 (5)	0.8985 (4)	0.0480 (12)
C18	0.2005 (5)	−0.0854 (5)	0.9460 (4)	0.0496 (13)
H18	0.1943	−0.1493	0.9315	0.060*
C19	0.3118 (4)	−0.1151 (5)	1.0143 (4)	0.0496 (13)
C20	0.3311 (4)	−0.0229 (5)	1.0410 (3)	0.0456 (12)
C21	0.2194 (5)	0.1088 (5)	0.9812 (4)	0.0472 (12)
C22	0.1076 (4)	0.1381 (5)	0.9134 (4)	0.0488 (13)
H22	0.0392	0.2234	0.8776	0.059*
O9	0.5277 (3)	0.3378 (4)	0.6011 (3)	0.0581 (10)
N8	0.5913 (4)	0.1433 (4)	0.6002 (3)	0.0551 (12)
C23	0.6860 (5)	0.0045 (5)	0.6489 (4)	0.0723 (18)
H23A	0.7387	−0.0147	0.5950	0.087*
H23B	0.6355	−0.0454	0.6710	0.087*
H23C	0.7461	−0.0176	0.7128	0.087*
C24	0.4876 (5)	0.1923 (6)	0.5051 (4)	0.0651 (16)
H24A	0.4192	0.2779	0.4908	0.078*
H24B	0.4459	0.1350	0.5211	0.078*
H24C	0.5295	0.1961	0.4408	0.078*
C25	0.6028 (5)	0.2181 (5)	0.6400 (4)	0.0551 (14)
H25	0.6710	0.1799	0.7010	0.066*
O10	0.1119 (11)	0.8119 (10)	0.6125 (7)	0.161 (4)	0.715 (6)
N9	0.1418 (5)	0.6993 (7)	0.7922 (6)	0.068 (2)	0.715 (6)
C26	0.2883 (6)	0.6379 (9)	0.7915 (9)	0.095 (4)	0.715 (6)
H26A	0.3044	0.6737	0.7170	0.143*	0.715 (6)
H26B	0.3205	0.5457	0.8187	0.143*	0.715 (6)
H26C	0.3360	0.6541	0.8384	0.143*	0.715 (6)
C27	0.0966 (8)	0.6585 (9)	0.8996 (6)	0.081 (3)	0.715 (6)
H27A	−0.0009	0.7062	0.8888	0.122*	0.715 (6)
H27B	0.1386	0.6758	0.9493	0.122*	0.715 (6)
H27C	0.1225	0.5670	0.9309	0.122*	0.715 (6)
C28	0.0578 (8)	0.7873 (8)	0.6984 (6)	0.071 (3)	0.715 (6)
H28A	−0.0359	0.8292	0.6950	0.085*	0.715 (6)
O10A	0.3069 (17)	0.6919 (19)	0.6726 (13)	0.100*	0.285 (6)
N9A	0.1822 (19)	0.667 (3)	0.8055 (15)	0.100*	0.285 (6)
C26A	0.303 (2)	0.552 (2)	0.8825 (17)	0.100*	0.285 (6)
H26D	0.3777	0.5331	0.8430	0.150*	0.285 (6)
H26E	0.2838	0.4784	0.9143	0.150*	0.285 (6)
H26F	0.3281	0.5688	0.9406	0.150*	0.285 (6)
C27A	0.0588 (19)	0.700 (3)	0.8533 (19)	0.100*	0.285 (6)
H27D	−0.0151	0.7755	0.7973	0.150*	0.285 (6)
H27E	0.0739	0.7182	0.9135	0.150*	0.285 (6)
H27F	0.0364	0.6282	0.8806	0.150*	0.285 (6)
C28A	0.1935 (19)	0.729 (2)	0.7029 (14)	0.100*	0.285 (6)
H28B	0.1175	0.8016	0.6525	0.120*	0.285 (6)
H2N	0.400 (4)	0.199 (6)	0.792 (4)	0.08 (2)*
H4N	0.374 (5)	0.587 (5)	0.357 (4)	0.069 (18)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu	0.0295 (4)	0.0509 (6)	0.0466 (5)	−0.0148 (4)	0.0089 (3)	−0.0273 (4)
O1	0.0332 (15)	0.051 (2)	0.0461 (17)	−0.0136 (15)	0.0083 (14)	−0.0237 (16)
O2	0.045 (2)	0.073 (3)	0.077 (3)	−0.011 (2)	−0.0100 (19)	−0.021 (2)
O3	0.058 (2)	0.081 (3)	0.070 (2)	−0.029 (2)	−0.0037 (19)	−0.033 (2)
O4	0.063 (2)	0.059 (3)	0.068 (2)	−0.0146 (19)	0.0012 (18)	−0.037 (2)
O5	0.081 (3)	0.064 (3)	0.064 (2)	−0.002 (2)	−0.032 (2)	−0.026 (2)
O6	0.0501 (19)	0.060 (2)	0.0532 (19)	−0.0160 (17)	−0.0023 (16)	−0.0245 (18)
O7	0.136 (5)	0.082 (4)	0.197 (6)	0.010 (3)	−0.097 (5)	−0.082 (4)
O8	0.084 (3)	0.059 (3)	0.088 (3)	−0.019 (2)	−0.011 (2)	−0.026 (2)
N1	0.0338 (18)	0.051 (3)	0.047 (2)	−0.0186 (18)	0.0123 (17)	−0.027 (2)
N2	0.0352 (19)	0.054 (3)	0.044 (2)	−0.0163 (19)	0.0124 (18)	−0.027 (2)
N3	0.0315 (17)	0.054 (3)	0.045 (2)	−0.0156 (18)	0.0086 (16)	−0.027 (2)
N4	0.0325 (19)	0.058 (3)	0.059 (2)	−0.019 (2)	0.0144 (19)	−0.028 (2)
N5	0.041 (2)	0.080 (4)	0.047 (2)	−0.023 (2)	0.0048 (19)	−0.027 (3)
N6	0.052 (2)	0.059 (3)	0.057 (2)	−0.015 (2)	0.007 (2)	−0.032 (2)
N7	0.051 (2)	0.063 (3)	0.048 (2)	−0.007 (2)	−0.002 (2)	−0.030 (2)
C1	0.037 (2)	0.055 (3)	0.045 (2)	−0.021 (2)	0.015 (2)	−0.029 (2)
C2	0.043 (2)	0.058 (3)	0.048 (3)	−0.022 (2)	0.012 (2)	−0.026 (3)
C3	0.061 (3)	0.063 (4)	0.053 (3)	−0.030 (3)	0.018 (3)	−0.033 (3)
C4	0.067 (3)	0.054 (4)	0.059 (3)	−0.026 (3)	0.025 (3)	−0.030 (3)
C5	0.045 (2)	0.058 (3)	0.042 (2)	−0.015 (2)	0.009 (2)	−0.028 (2)
C6	0.037 (2)	0.048 (3)	0.041 (2)	−0.013 (2)	0.013 (2)	−0.022 (2)
C7	0.0260 (19)	0.061 (3)	0.042 (2)	−0.012 (2)	0.0078 (18)	−0.030 (2)
C8	0.039 (2)	0.058 (3)	0.044 (2)	−0.017 (2)	0.002 (2)	−0.027 (2)
C9	0.035 (2)	0.059 (3)	0.053 (3)	−0.021 (2)	0.010 (2)	−0.028 (3)
C10	0.031 (2)	0.058 (3)	0.053 (3)	−0.017 (2)	0.009 (2)	−0.030 (2)
C11	0.036 (2)	0.057 (3)	0.049 (3)	−0.011 (2)	0.009 (2)	−0.027 (3)
C12	0.043 (3)	0.073 (4)	0.062 (3)	−0.021 (3)	0.021 (2)	−0.036 (3)
C13	0.048 (3)	0.096 (5)	0.075 (3)	−0.024 (3)	0.027 (3)	−0.059 (4)
C14	0.057 (3)	0.085 (5)	0.070 (3)	−0.026 (3)	0.021 (3)	−0.052 (3)
C15	0.041 (2)	0.070 (4)	0.062 (3)	−0.021 (3)	0.014 (2)	−0.038 (3)
C16	0.031 (2)	0.053 (3)	0.047 (2)	−0.012 (2)	0.0093 (19)	−0.027 (2)
C17	0.038 (2)	0.059 (3)	0.043 (2)	−0.018 (2)	0.008 (2)	−0.023 (2)
C18	0.046 (3)	0.064 (4)	0.041 (2)	−0.027 (3)	0.014 (2)	−0.023 (2)
C19	0.040 (2)	0.057 (3)	0.043 (2)	−0.010 (2)	0.005 (2)	−0.026 (2)
C20	0.041 (2)	0.052 (3)	0.033 (2)	−0.013 (2)	0.008 (2)	−0.017 (2)
C21	0.047 (3)	0.052 (3)	0.043 (2)	−0.017 (2)	0.016 (2)	−0.027 (2)
C22	0.036 (2)	0.058 (3)	0.041 (2)	−0.010 (2)	0.007 (2)	−0.022 (2)
O9	0.0464 (18)	0.070 (3)	0.062 (2)	−0.0275 (19)	0.0155 (17)	−0.032 (2)
N8	0.038 (2)	0.067 (3)	0.052 (2)	−0.014 (2)	0.0108 (18)	−0.028 (2)
C23	0.055 (3)	0.072 (4)	0.070 (3)	−0.009 (3)	0.013 (3)	−0.034 (3)
C24	0.056 (3)	0.077 (4)	0.053 (3)	−0.018 (3)	0.003 (3)	−0.032 (3)
C25	0.038 (2)	0.079 (4)	0.055 (3)	−0.027 (3)	0.015 (2)	−0.035 (3)
O10	0.230 (12)	0.138 (9)	0.169 (9)	−0.105 (9)	0.009 (9)	−0.091 (8)
N9	0.016 (3)	0.079 (5)	0.137 (7)	−0.012 (3)	0.021 (3)	−0.082 (5)
C26	0.025 (3)	0.086 (7)	0.202 (13)	−0.011 (4)	0.008 (5)	−0.102 (9)
C27	0.082 (6)	0.054 (6)	0.077 (6)	−0.025 (5)	−0.019 (5)	−0.006 (5)
C28	0.087 (6)	0.078 (7)	0.079 (6)	−0.055 (6)	0.027 (5)	−0.046 (6)

Geometric parameters (Å, º) top

Cu—N3	1.979 (3)	C13—C14	1.392 (8)
Cu—N3ⁱ	1.979 (3)	C13—H13	0.9300
Cu—N1	1.992 (4)	C14—C15	1.375 (6)
Cu—N1ⁱ	1.992 (4)	C14—H14	0.9300
Cu—O1ⁱ	2.583 (3)	C15—C16	1.395 (7)
Cu—O1	2.583 (3)	C15—H15	0.9300
O1—C9	1.427 (5)	C17—C22	1.373 (7)
O1—C8	1.429 (5)	C17—C18	1.382 (7)
O2—N5	1.227 (6)	C18—C19	1.363 (6)
O3—N5	1.227 (6)	C18—H18	0.9300
O4—N6	1.230 (5)	C19—C20	1.440 (7)
O5—N6	1.228 (5)	C20—C21	1.465 (7)
O6—C20	1.244 (5)	C21—C22	1.366 (6)
O7—N7	1.185 (5)	C22—H22	0.9300
O8—N7	1.199 (6)	O9—C25	1.248 (6)
N1—C7	1.324 (5)	N8—C25	1.306 (6)
N1—C1	1.387 (6)	N8—C23	1.461 (6)
N2—C7	1.342 (6)	N8—C24	1.461 (5)
N2—C6	1.386 (6)	C23—H23A	0.9600
N2—H2N	0.87 (5)	C23—H23B	0.9600
N3—C10	1.329 (6)	C23—H23C	0.9600
N3—C16	1.413 (5)	C24—H24A	0.9600
N4—C10	1.339 (6)	C24—H24B	0.9600
N4—C11	1.389 (6)	C24—H24C	0.9600
N4—H4N	0.87 (5)	C25—H25	0.9300
N5—C17	1.451 (6)	O10—C28	1.266 (7)
N6—C19	1.451 (6)	N9—C28	1.309 (7)
N7—C21	1.456 (7)	N9—C26	1.463 (6)
C1—C2	1.395 (6)	N9—C27	1.468 (6)
C1—C6	1.399 (6)	C26—H26A	0.9600
C2—C3	1.373 (8)	C26—H26B	0.9600
C2—H2	0.9300	C26—H26C	0.9600
C3—C4	1.397 (7)	C27—H27A	0.9600
C3—H3	0.9300	C27—H27B	0.9600
C4—C5	1.374 (7)	C27—H27C	0.9600
C4—H4	0.9300	C28—H28A	0.9300
C5—C6	1.372 (7)	O10A—C28A	1.255 (8)
C5—H5	0.9300	N9A—C28A	1.309 (7)
C7—C8	1.490 (7)	N9A—C27A	1.456 (7)
C8—H8A	0.9700	N9A—C26A	1.466 (7)
C8—H8B	0.9700	C26A—H26D	0.9600
C9—C10	1.489 (6)	C26A—H26E	0.9600
C9—H9A	0.9700	C26A—H26F	0.9600
C9—H9B	0.9700	C27A—H27D	0.9600
C11—C16	1.380 (7)	C27A—H27E	0.9600
C11—C12	1.394 (6)	C27A—H27F	0.9600
C12—C13	1.381 (8)	C28A—H28B	0.9300
C12—H12	0.9300

N3—Cu—N3ⁱ	180	C14—C13—H13	118.8
N3—Cu—N1	87.55 (15)	C15—C14—C13	121.4 (5)
N3ⁱ—Cu—N1	92.45 (15)	C15—C14—H14	119.3
N3—Cu—N1ⁱ	92.45 (15)	C13—C14—H14	119.3
N3ⁱ—Cu—N1ⁱ	87.55 (15)	C14—C15—C16	117.1 (5)
N1—Cu—N1ⁱ	180	C14—C15—H15	121.5
N3—Cu—O1ⁱ	106.54 (12)	C16—C15—H15	121.5
N3ⁱ—Cu—O1ⁱ	73.46 (12)	C11—C16—C15	120.9 (4)
N1—Cu—O1ⁱ	106.14 (13)	C11—C16—N3	109.3 (4)
N1ⁱ—Cu—O1ⁱ	73.86 (13)	C15—C16—N3	129.7 (4)
N3—Cu—O1	73.46 (12)	C22—C17—C18	121.3 (4)
N3ⁱ—Cu—O1	106.54 (12)	C22—C17—N5	119.6 (5)
N1—Cu—O1	73.86 (13)	C18—C17—N5	119.1 (5)
N1ⁱ—Cu—O1	106.14 (13)	C19—C18—C17	119.2 (5)
O1ⁱ—Cu—O1	180	C19—C18—H18	120.4
C9—O1—C8	114.0 (3)	C17—C18—H18	120.4
C9—O1—Cu	105.0 (2)	C18—C19—C20	124.5 (5)
C8—O1—Cu	104.8 (3)	C18—C19—N6	115.8 (5)
C7—N1—C1	105.4 (4)	C20—C19—N6	119.7 (4)
C7—N1—Cu	122.5 (3)	O6—C20—C19	124.9 (4)
C1—N1—Cu	131.4 (3)	O6—C20—C21	123.4 (5)
C7—N2—C6	108.1 (4)	C19—C20—C21	111.7 (4)
C7—N2—H2N	124 (4)	C22—C21—N7	117.0 (5)
C6—N2—H2N	128 (4)	C22—C21—C20	123.6 (5)
C10—N3—C16	104.3 (4)	N7—C21—C20	119.4 (4)
C10—N3—Cu	123.2 (3)	C21—C22—C17	119.5 (5)
C16—N3—Cu	132.4 (3)	C21—C22—H22	120.3
C10—N4—C11	107.3 (4)	C17—C22—H22	120.3
C10—N4—H4N	120 (4)	C25—N8—C23	120.4 (4)
C11—N4—H4N	133 (4)	C25—N8—C24	122.9 (4)
O2—N5—O3	123.3 (4)	C23—N8—C24	116.7 (4)
O2—N5—C17	118.3 (5)	N8—C23—H23A	109.5
O3—N5—C17	118.4 (5)	N8—C23—H23B	109.5
O5—N6—O4	122.7 (4)	H23A—C23—H23B	109.5
O5—N6—C19	119.1 (4)	N8—C23—H23C	109.5
O4—N6—C19	118.2 (4)	H23A—C23—H23C	109.5
O7—N7—O8	120.8 (6)	H23B—C23—H23C	109.5
O7—N7—C21	120.5 (5)	N8—C24—H24A	109.5
O8—N7—C21	118.7 (4)	N8—C24—H24B	109.5
N1—C1—C2	131.0 (4)	H24A—C24—H24B	109.5
N1—C1—C6	109.6 (4)	N8—C24—H24C	109.5
C2—C1—C6	119.4 (5)	H24A—C24—H24C	109.5
C3—C2—C1	118.0 (4)	H24B—C24—H24C	109.5
C3—C2—H2	121.0	O9—C25—N8	124.0 (4)
C1—C2—H2	121.0	O9—C25—H25	118.0
C2—C3—C4	121.0 (5)	N8—C25—H25	118.0
C2—C3—H3	119.5	C28—N9—C26	119.1 (6)
C4—C3—H3	119.5	C28—N9—C27	123.2 (5)
C5—C4—C3	122.1 (5)	C26—N9—C27	117.7 (6)
C5—C4—H4	118.9	N9—C26—H26A	109.5
C3—C4—H4	118.9	N9—C26—H26B	109.5
C6—C5—C4	116.4 (4)	H26A—C26—H26B	109.5
C6—C5—H5	121.8	N9—C26—H26C	109.5
C4—C5—H5	121.8	H26A—C26—H26C	109.5
C5—C6—N2	132.3 (4)	H26B—C26—H26C	109.5
C5—C6—C1	123.1 (5)	N9—C27—H27A	109.5
N2—C6—C1	104.6 (4)	N9—C27—H27B	109.5
N1—C7—N2	112.3 (5)	H27A—C27—H27B	109.5
N1—C7—C8	123.6 (4)	N9—C27—H27C	109.5
N2—C7—C8	124.1 (4)	H27A—C27—H27C	109.5
O1—C8—C7	111.3 (3)	H27B—C27—H27C	109.5
O1—C8—H8A	109.4	O10—C28—N9	116.0 (7)
C7—C8—H8A	109.4	O10—C28—H28A	122.0
O1—C8—H8B	109.4	N9—C28—H28A	122.0
C7—C8—H8B	109.4	C28A—N9A—C27A	126.2 (9)
H8A—C8—H8B	108.0	C28A—N9A—C26A	118.7 (8)
O1—C9—C10	111.0 (4)	C27A—N9A—C26A	115.1 (8)
O1—C9—H9A	109.4	N9A—C26A—H26D	109.5
C10—C9—H9A	109.4	N9A—C26A—H26E	109.5
O1—C9—H9B	109.4	H26D—C26A—H26E	109.5
C10—C9—H9B	109.4	N9A—C26A—H26F	109.5
H9A—C9—H9B	108.0	H26D—C26A—H26F	109.5
N3—C10—N4	113.2 (4)	H26E—C26A—H26F	109.5
N3—C10—C9	123.3 (4)	N9A—C27A—H27D	109.5
N4—C10—C9	123.5 (4)	N9A—C27A—H27E	109.5
C16—C11—N4	106.0 (4)	H27D—C27A—H27E	109.5
C16—C11—C12	122.6 (5)	N9A—C27A—H27F	109.5
N4—C11—C12	131.4 (5)	H27D—C27A—H27F	109.5
C13—C12—C11	115.7 (5)	H27E—C27A—H27F	109.5
C13—C12—H12	122.2	O10A—C28A—N9A	120.0 (10)
C11—C12—H12	122.2	O10A—C28A—H28B	120.0
C12—C13—C14	122.3 (5)	N9A—C28A—H28B	120.0
C12—C13—H13	118.8

N3—Cu—O1—C9	15.0 (3)	C16—N3—C10—N4	0.2 (6)
N3ⁱ—Cu—O1—C9	−165.0 (3)	Cu—N3—C10—N4	177.0 (3)
N1—Cu—O1—C9	107.2 (3)	C16—N3—C10—C9	178.4 (4)
N1ⁱ—Cu—O1—C9	−72.8 (3)	Cu—N3—C10—C9	−4.8 (7)
O1ⁱ—Cu—O1—C9	−79 (100)	C11—N4—C10—N3	0.0 (6)
N3—Cu—O1—C8	−105.5 (3)	C11—N4—C10—C9	−178.1 (5)
N3ⁱ—Cu—O1—C8	74.5 (3)	O1—C9—C10—N3	19.8 (7)
N1—Cu—O1—C8	−13.2 (2)	O1—C9—C10—N4	−162.2 (4)
N1ⁱ—Cu—O1—C8	166.8 (2)	C10—N4—C11—C16	−0.3 (5)
O1ⁱ—Cu—O1—C8	161 (100)	C10—N4—C11—C12	−177.8 (6)
N3—Cu—N1—C7	76.3 (3)	C16—C11—C12—C13	−2.1 (8)
N3ⁱ—Cu—N1—C7	−103.7 (3)	N4—C11—C12—C13	175.1 (5)
N1ⁱ—Cu—N1—C7	−42 (100)	C11—C12—C13—C14	0.9 (9)
O1ⁱ—Cu—N1—C7	−177.2 (3)	C12—C13—C14—C15	0.1 (10)
O1—Cu—N1—C7	2.8 (3)	C13—C14—C15—C16	0.0 (9)
N3—Cu—N1—C1	−92.3 (4)	N4—C11—C16—C15	−175.4 (4)
N3ⁱ—Cu—N1—C1	87.7 (4)	C12—C11—C16—C15	2.4 (8)
N1ⁱ—Cu—N1—C1	149 (100)	N4—C11—C16—N3	0.4 (6)
O1ⁱ—Cu—N1—C1	14.2 (4)	C12—C11—C16—N3	178.2 (5)
O1—Cu—N1—C1	−165.8 (4)	C14—C15—C16—C11	−1.2 (8)
N3ⁱ—Cu—N3—C10	153 (100)	C14—C15—C16—N3	−176.1 (5)
N1—Cu—N3—C10	−79.7 (4)	C10—N3—C16—C11	−0.4 (5)
N1ⁱ—Cu—N3—C10	100.3 (4)	Cu—N3—C16—C11	−176.8 (3)
O1ⁱ—Cu—N3—C10	174.2 (4)	C10—N3—C16—C15	175.0 (5)
O1—Cu—N3—C10	−5.8 (4)	Cu—N3—C16—C15	−1.4 (8)
N3ⁱ—Cu—N3—C16	−31 (100)	O2—N5—C17—C22	2.5 (7)
N1—Cu—N3—C16	96.1 (4)	O3—N5—C17—C22	−176.7 (4)
N1ⁱ—Cu—N3—C16	−83.9 (4)	O2—N5—C17—C18	−175.6 (4)
O1ⁱ—Cu—N3—C16	−10.0 (4)	O3—N5—C17—C18	5.3 (6)
O1—Cu—N3—C16	170.0 (4)	C22—C17—C18—C19	3.9 (7)
C7—N1—C1—C2	−177.3 (4)	N5—C17—C18—C19	−178.1 (4)
Cu—N1—C1—C2	−7.2 (7)	C17—C18—C19—C20	−0.5 (7)
C7—N1—C1—C6	1.0 (5)	C17—C18—C19—N6	−178.4 (4)
Cu—N1—C1—C6	171.1 (3)	O5—N6—C19—C18	−152.7 (5)
N1—C1—C2—C3	179.6 (4)	O4—N6—C19—C18	27.1 (7)
C6—C1—C2—C3	1.5 (6)	O5—N6—C19—C20	29.3 (7)
C1—C2—C3—C4	−1.5 (7)	O4—N6—C19—C20	−150.9 (4)
C2—C3—C4—C5	0.6 (7)	C18—C19—C20—O6	178.7 (4)
C3—C4—C5—C6	0.3 (7)	N6—C19—C20—O6	−3.5 (7)
C4—C5—C6—N2	−178.4 (4)	C18—C19—C20—C21	−2.9 (6)
C4—C5—C6—C1	−0.4 (7)	N6—C19—C20—C21	174.9 (4)
C7—N2—C6—C5	178.2 (5)	O7—N7—C21—C22	167.0 (6)
C7—N2—C6—C1	−0.2 (4)	O8—N7—C21—C22	−10.0 (7)
N1—C1—C6—C5	−179.0 (4)	O7—N7—C21—C20	−13.8 (8)
C2—C1—C6—C5	−0.6 (7)	O8—N7—C21—C20	169.2 (4)
N1—C1—C6—N2	−0.5 (5)	O6—C20—C21—C22	−178.2 (4)
C2—C1—C6—N2	178.0 (4)	C19—C20—C21—C22	3.3 (6)
C1—N1—C7—N2	−1.1 (5)	O6—C20—C21—N7	2.6 (6)
Cu—N1—C7—N2	−172.3 (3)	C19—C20—C21—N7	−175.8 (4)
C1—N1—C7—C8	−179.9 (4)	N7—C21—C22—C17	178.8 (4)
Cu—N1—C7—C8	8.9 (6)	C20—C21—C22—C17	−0.3 (7)
C6—N2—C7—N1	0.8 (5)	C18—C17—C22—C21	−3.5 (7)
C6—N2—C7—C8	179.6 (4)	N5—C17—C22—C21	178.5 (4)
C9—O1—C8—C7	−94.6 (4)	C23—N8—C25—O9	178.3 (5)
Cu—O1—C8—C7	19.7 (4)	C24—N8—C25—O9	−0.3 (7)
N1—C7—C8—O1	−21.8 (6)	C26—N9—C28—O10	0.4 (13)
N2—C7—C8—O1	159.6 (4)	C27—N9—C28—O10	−179.7 (9)
C8—O1—C9—C10	94.0 (4)	C27A—N9A—C28A—O10A	178 (3)
Cu—O1—C9—C10	−20.2 (4)	C26A—N9A—C28A—O10A	−1 (5)

Symmetry code: (i) −x, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2N···O6ⁱⁱ	0.87 (5)	1.95 (4)	2.709 (5)	145 (6)
N2—H2N···O5ⁱⁱ	0.87 (5)	2.41 (5)	3.104 (6)	138 (6)
N4—H4N···O9ⁱⁱⁱ	0.87 (5)	1.92 (2)	2.753 (6)	162 (5)

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

Experimental details

Crystal data
Chemical formula	[Cu(C₁₆H₁₄N₄O)₂](C₆H₂N₃O₇)₂·4C₃H₇NO
M_r	1368.77
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	10.9656 (7), 12.6028 (12), 13.4100 (9)
α, β, γ (°)	65.746 (2), 88.629 (2), 65.187 (2)
V (Å³)	1508.8 (2)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	0.46
Crystal size (mm)	0.28 × 0.21 × 0.11

Data collection
Diffractometer	Rigaku R-AXIS Spider diffractometer
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995)
T_min, T_max	0.883, 0.952
No. of measured, independent and observed [I > 2σ(I)] reflections	12429, 5605, 3363
R_int	0.078
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.075, 0.232, 1.02
No. of reflections	5605
No. of parameters	457
No. of restraints	18
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.78, −1.09

Computer programs: RAPID-AUTO (Rigaku/MSC, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2003), SHELXTL (Sheldrick, 2008).

Selected geometric parameters (Å, º) top

Cu—N3	1.979 (3)	Cu—O1	2.583 (3)
Cu—N1	1.992 (4)

N3—Cu—N3ⁱ	180	N1—Cu—O1ⁱ	106.14 (13)
N3—Cu—N1	87.55 (15)	N3—Cu—O1	73.46 (12)
N3—Cu—N1ⁱ	92.45 (15)	N1—Cu—O1	73.86 (13)
N1—Cu—N1ⁱ	180	O1ⁱ—Cu—O1	180
N3—Cu—O1ⁱ	106.54 (12)

Symmetry code: (i) −x, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2N···O6ⁱⁱ	0.87 (5)	1.95 (4)	2.709 (5)	145 (6)
N2—H2N···O5ⁱⁱ	0.87 (5)	2.41 (5)	3.104 (6)	138 (6)
N4—H4N···O9ⁱⁱⁱ	0.87 (5)	1.92 (2)	2.753 (6)	162 (5)

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

Acknowledgements

The authors acknowledge the financial support and grant from Qing Lan Talent Engineering Funds (QL-05–03 A) of Lanzhou Jiaotong University. The Middle-Young Age Science Foundation of Gansu Province (grant No. 3YS061-A25–023,24) is also acknowledged.

References

Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan. Google Scholar
Rigaku/MSC (2004). RAPID-AUTO. Rigaku/MSC, The Woodlands, Texas, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2003). J. Appl. Cryst. 36, 7–13. Web of Science CrossRef CAS IUCr Journals Google Scholar
Zhou, H.-Q. & Yang, P. (2006). Huaxue Xuebao, 64, 793. Google Scholar

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Volume 64| Part 12| December 2008| Page m1529

doi:10.1107/S1600536808036829

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

Bis[1,3-bis­­(benzimidazol-2-yl)-2-oxa­propane]copper(II)–picrate–di­methyl­formamide (1/2/4)

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

metal-organic compounds

Bis[1,3-bis(benzimidazol-2-yl)-2-oxapropane]copper(II)–picrate–dimethylformamide (1/2/4)