catena-Poly[[(1,3-dimethyl­imidazolin-2-one-κN)(1,10-phenanthroline-κ2N,N′)copper(II)]-μ-furan-2,5-dicarboxyl­ato-κ2O2:O5]

Li, Y.-F.; Xu, Y.; Qin, X.-L.; Yuan, Y.-P.; Gao, W.-Y.

doi:10.1107/S160053681203111X

metal-organic compounds

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ISSN: 2056-9890

Volume 68| Part 9| September 2012| Page m1140

doi:10.1107/S160053681203111X

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catena-Poly[[(1,3-dimethylimidazolin-2-one-κN)(1,10-phenanthroline-κ²N,N′)copper(II)]-μ-furan-2,5-dicarboxylato-κ²O²:O⁵]

Ya-Feng Li,^a ^* Yue Xu,^a Xiao-Lin Qin,^a Yong-Peng Yuan ^a and Wen-Yuan Gao ^a

^aSchool of Chemical Engineering, Changchun University of Technology, Changchun 130012, People's Republic of China
^*Correspondence e-mail: fly012345@sohu.com

(Received 2 July 2012; accepted 8 July 2012; online 1 August 2012)

The polymeric title compound, [Cu(C₆H₂O₅)(C₁₂H₈N₂)(C₅H₁₀N₂O)]_n, is composed of an infinite chain formed along [100] by linking the (1,3-dimethylimidazolin-2-one)(1,10-phenanthroline)copper(II) units with two O atoms of two carboxylate groups of the furan-2,5-dicarboxylate ligand. The Cu^II atom, which lies on a twofold rotation axis, displays a square-pyramidal coordination. The dihedral angles of the 1,10-phenanthroline ligand with respect to the furan rings of the carboxylate anions that are connected to the metal atom are 62.18 (11) and 88.27 (12)°.

Related literature

For related structures, see: Li, et al. (2012a ,b ).

Experimental

Crystal data

[Cu(C₆H₂O₅)(C₁₂H₈N₂)(C₅H₁₀N₂O)]
M_r = 511.98
Orthorhombic, P b c a
a = 15.620 (3) Å
b = 14.598 (3) Å
c = 18.616 (4) Å
V = 4244.8 (15) Å³
Z = 8
Mo Kα radiation
μ = 1.08 mm⁻¹
T = 293 K
0.10 × 0.10 × 0.10 mm

Data collection

Rigaku R-AXIS RAPID diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ) T_min = 0.900, T_max = 0.900
30193 measured reflections
3727 independent reflections
2376 reflections with I > 2σ(I)
R_int = 0.110

Refinement

R[F² > 2σ(F²)] = 0.047
wR(F²) = 0.109
S = 1.04
3727 reflections
309 parameters
H-atom parameters constrained
Δρ_max = 0.46 e Å⁻³
Δρ_min = −0.37 e Å⁻³

Data collection: PROCESS-AUTO (Rigaku, 1998 ); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002 ); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2000 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053681203111X/ng5281sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681203111X/ng5281Isup2.hkl

checkCIF report

Comment top

Recently, we utilized furan-2,5-dicarboxylate anion as the ligand to synthesize MOFs (Li et al., 2012a,b). In this work, we report a chainlike compound, [Cu(C₅H₁₀N₂O)(C₁₂H₈N₂)(C₆H₂O₅)]_n (Scheme I), is structurally determined.

The asymmetric unit of (I) is consists of one Cu(II) cation, one furan-2,5-dicarboxylate anion, one 1,3-dimethyl-2-imidazolinone molecule and one 1,10-phenanthroline molecule (Fig.1). The Cu atom is coordinated by two carboxylate O atoms, two N atoms of one C₁₂H₈N₂ and one nitrogen of from C₅H₁₀N₂O. The geometry is a square pyramid. The furan-2,5-dicarboxylate shows a µ₂:η¹;η¹ coordinated mode. The dihedral angles of C₁₂H₈N₂ with respect to the furan rings of the carboxylates that are coordinated to the same Cu atom are 62.18 (11)° and 88.27 (12)° (Fig. 1).

The Cu atom is linked by two furan-2,5-dicarboxylates to give rise to an infinite chain (Fig.2).

Related literature top

For related structures, see: Li, et al. (2012a,b).

Experimental top

Furan-2,5-dicarboxylic acid (0.0156 g, 0.10 mmol), Cu(NO₃)₂^.6H₂O (0.0298 g, 0.10 mmol), and C₁₂H₈N₂ (0.0198, 0.11 mmol) were dissolved in DMI (5 ml, 48 mmol) under stirring. The mixture with molar ratio of 1 furan-2,5-dicarboxylic acid: 1 Cu(NO₃)₂^.6H₂O: 1.1 C₁₂H₈N₂: 480 DMI was heated at 393 K for 2 days. Blue block were collected as a single phase.

Computing details top

Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO (Rigaku, 1998); data reduction: CrystalStructure (Rigaku/MSC, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2000); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The asymmetric unit of (I), showing the atomic labelling scheme and displacement ellipsoids at the 50% probability level. [Symmetry codes: (i) 0.5 + x, y, 0.5 - z.]
	Fig. 2. The stick plot of (I), displaying the infinite chain formed by linking the Cu with two oxygen atoms of two carboxyls of furan-2,5-dicarboxylate.

catena-Poly[[(1,3-dimethylimidazolin-2-one-κN)(1,10- phenanthroline-κ²N,N')copper(II)]-µ-furan-2,5-dicarboxylato- κ²O²:O⁵] top

Crystal data top

[Cu(C₆H₂O₅)(C₁₂H₈N₂)(C₅H₁₀N₂O)]	F(000) = 2104
M_r = 511.98	D_x = 1.602 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 2000 reflections
a = 15.620 (3) Å	θ = 3.0–25.0°
b = 14.598 (3) Å	µ = 1.08 mm⁻¹
c = 18.616 (4) Å	T = 293 K
V = 4244.8 (15) Å³	Block, blue
Z = 8	0.10 × 0.10 × 0.10 mm

Data collection top

Rigaku R-AXIS RAPID diffractometer	3727 independent reflections
Radiation source: fine-focus sealed tube	2376 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.110
Detector resolution: 10.00 pixels mm^-1	θ_max = 25.0°, θ_min = 3.0°
ω scans	h = −18→18
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	k = −17→17
T_min = 0.900, T_max = 0.900	l = −22→20
30193 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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.109	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0447P)² + 0.2947P] where P = (F_o² + 2F_c²)/3
3727 reflections	(Δ/σ)_max < 0.001
309 parameters	Δρ_max = 0.46 e Å⁻³
0 restraints	Δρ_min = −0.37 e Å⁻³

Crystal data top

[Cu(C₆H₂O₅)(C₁₂H₈N₂)(C₅H₁₀N₂O)]	V = 4244.8 (15) Å³
M_r = 511.98	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 15.620 (3) Å	µ = 1.08 mm⁻¹
b = 14.598 (3) Å	T = 293 K
c = 18.616 (4) Å	0.10 × 0.10 × 0.10 mm

Data collection top

Rigaku R-AXIS RAPID diffractometer	3727 independent reflections
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	2376 reflections with I > 2σ(I)
T_min = 0.900, T_max = 0.900	R_int = 0.110
30193 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	0 restraints
wR(F²) = 0.109	H-atom parameters constrained
S = 1.04	Δρ_max = 0.46 e Å⁻³
3727 reflections	Δρ_min = −0.37 e Å⁻³
309 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
Cu1	0.24404 (3)	0.39844 (3)	0.43722 (2)	0.03211 (16)
O1	0.14532 (17)	0.4367 (2)	0.38161 (13)	0.0416 (7)
O2	0.12024 (19)	0.2971 (2)	0.33748 (15)	0.0486 (8)
O3	−0.00981 (17)	0.36718 (18)	0.25302 (14)	0.0359 (6)
O4	−0.17851 (18)	0.4375 (2)	0.13743 (13)	0.0427 (7)
O5	−0.12344 (19)	0.2972 (2)	0.15283 (14)	0.0457 (8)
O6	0.36449 (19)	0.5888 (2)	0.54050 (16)	0.0542 (8)
N1	0.3387 (2)	0.3743 (2)	0.50900 (16)	0.0323 (8)
N2	0.1712 (2)	0.3470 (2)	0.51765 (16)	0.0331 (8)
N3	0.2429 (2)	0.5747 (3)	0.60884 (18)	0.0493 (9)
N4	0.2290 (2)	0.5799 (2)	0.48911 (17)	0.0411 (9)
C1	0.1065 (2)	0.3789 (3)	0.34036 (19)	0.0331 (9)
C2	0.0400 (2)	0.4234 (3)	0.29553 (19)	0.0355 (10)
C3	0.0156 (3)	0.5122 (3)	0.2869 (2)	0.0438 (11)
H3	0.0392	0.5632	0.3094	0.053*
C4	−0.0534 (3)	0.5117 (3)	0.2366 (2)	0.0434 (11)
H4	−0.0833	0.5626	0.2200	0.052*
C5	−0.0672 (3)	0.4228 (3)	0.21737 (19)	0.0355 (10)
C6	−0.1268 (2)	0.3795 (3)	0.16585 (19)	0.0337 (10)
C7	0.4221 (3)	0.3874 (3)	0.5029 (2)	0.0430 (10)
H7	0.4432	0.4125	0.4605	0.052*
C8	0.4805 (3)	0.3649 (3)	0.5581 (2)	0.0500 (12)
H8	0.5391	0.3719	0.5511	0.060*
C9	0.4493 (3)	0.3325 (3)	0.6221 (2)	0.0471 (12)
H9	0.4868	0.3178	0.6591	0.057*
C10	0.3614 (3)	0.3216 (3)	0.6314 (2)	0.0386 (10)
C11	0.3216 (3)	0.2927 (3)	0.6978 (2)	0.0478 (11)
H11	0.3558	0.2809	0.7377	0.057*
C12	0.2360 (3)	0.2825 (3)	0.7033 (2)	0.0481 (12)
H12	0.2123	0.2652	0.7470	0.058*
C13	0.1811 (3)	0.2980 (3)	0.6430 (2)	0.0394 (10)
C14	0.0921 (3)	0.2848 (3)	0.6432 (2)	0.0459 (11)
H14	0.0648	0.2653	0.6848	0.055*
C15	0.0454 (3)	0.3007 (3)	0.5821 (2)	0.0486 (12)
H15	−0.0134	0.2907	0.5816	0.058*
C16	0.0877 (3)	0.3324 (3)	0.5202 (2)	0.0417 (11)
H16	0.0554	0.3436	0.4792	0.050*
C17	0.2179 (3)	0.3287 (2)	0.5782 (2)	0.0324 (9)
C18	0.3083 (3)	0.3418 (3)	0.57286 (19)	0.0323 (9)
C19	0.2874 (3)	0.5825 (3)	0.5464 (2)	0.0400 (10)
C20	0.1433 (3)	0.5936 (3)	0.5180 (2)	0.0526 (12)
H20A	0.1018	0.5556	0.4932	0.063*
H20B	0.1260	0.6572	0.5142	0.063*
C21	0.1525 (3)	0.5647 (3)	0.5963 (3)	0.0528 (12)
H21A	0.1196	0.6044	0.6277	0.063*
H21B	0.1343	0.5019	0.6033	0.063*
C22	0.2507 (3)	0.6290 (3)	0.4228 (2)	0.0554 (12)
H22A	0.2415	0.6934	0.4296	0.066*
H22B	0.2152	0.6073	0.3843	0.066*
H22C	0.3098	0.6183	0.4112	0.066*
C23	0.2837 (3)	0.5516 (3)	0.6760 (2)	0.0618 (15)
H23A	0.2734	0.4883	0.6869	0.074*
H23B	0.2607	0.5892	0.7136	0.074*
H23C	0.3442	0.5621	0.6721	0.074*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.0273 (3)	0.0421 (3)	0.0270 (2)	0.0001 (2)	0.0005 (2)	0.0016 (2)
O1	0.0385 (17)	0.0466 (17)	0.0397 (15)	−0.0005 (14)	−0.0093 (13)	0.0014 (14)
O2	0.048 (2)	0.049 (2)	0.0492 (19)	0.0075 (16)	−0.0027 (14)	−0.0014 (15)
O3	0.0321 (16)	0.0415 (15)	0.0342 (14)	0.0000 (13)	−0.0061 (12)	−0.0016 (14)
O4	0.0398 (17)	0.0527 (19)	0.0358 (15)	0.0101 (14)	−0.0112 (13)	−0.0074 (14)
O5	0.054 (2)	0.0447 (19)	0.0387 (16)	−0.0043 (15)	−0.0034 (14)	0.0004 (14)
O6	0.0372 (19)	0.064 (2)	0.062 (2)	−0.0037 (16)	0.0009 (15)	−0.0073 (16)
N1	0.0288 (19)	0.0338 (19)	0.0345 (18)	0.0003 (14)	0.0025 (14)	−0.0018 (15)
N2	0.031 (2)	0.037 (2)	0.0317 (18)	−0.0033 (15)	−0.0017 (15)	−0.0043 (15)
N3	0.047 (2)	0.057 (2)	0.0432 (19)	−0.004 (2)	0.0001 (19)	−0.0054 (17)
N4	0.039 (2)	0.047 (2)	0.0373 (18)	−0.0009 (16)	−0.0022 (15)	−0.0010 (17)
C1	0.030 (2)	0.043 (3)	0.027 (2)	−0.0016 (19)	0.0059 (16)	−0.0017 (19)
C2	0.027 (2)	0.052 (3)	0.028 (2)	−0.0020 (19)	0.0009 (16)	−0.0091 (19)
C3	0.041 (3)	0.047 (3)	0.043 (2)	−0.001 (2)	−0.006 (2)	−0.004 (2)
C4	0.050 (3)	0.040 (3)	0.040 (2)	0.006 (2)	−0.008 (2)	0.002 (2)
C5	0.030 (2)	0.048 (3)	0.028 (2)	0.0077 (19)	0.0003 (17)	0.0025 (19)
C6	0.027 (2)	0.050 (3)	0.024 (2)	0.001 (2)	0.0043 (16)	0.0016 (19)
C7	0.033 (2)	0.055 (3)	0.041 (2)	−0.002 (2)	−0.0002 (18)	−0.004 (2)
C8	0.031 (2)	0.064 (3)	0.055 (3)	0.004 (2)	−0.003 (2)	−0.007 (3)
C9	0.048 (3)	0.049 (3)	0.045 (3)	0.009 (2)	−0.014 (2)	−0.004 (2)
C10	0.046 (3)	0.034 (2)	0.035 (2)	0.008 (2)	−0.005 (2)	−0.0051 (19)
C11	0.070 (3)	0.038 (3)	0.035 (2)	0.006 (2)	−0.006 (2)	0.002 (2)
C12	0.067 (4)	0.044 (3)	0.033 (2)	0.002 (2)	0.009 (2)	0.004 (2)
C13	0.056 (3)	0.029 (2)	0.033 (2)	−0.006 (2)	0.010 (2)	−0.0004 (18)
C14	0.053 (3)	0.036 (2)	0.049 (3)	−0.008 (2)	0.024 (2)	−0.002 (2)
C15	0.038 (3)	0.049 (3)	0.059 (3)	−0.009 (2)	0.015 (2)	−0.010 (2)
C16	0.034 (3)	0.050 (3)	0.041 (2)	−0.004 (2)	0.0025 (19)	−0.003 (2)
C17	0.038 (2)	0.023 (2)	0.036 (2)	−0.0011 (16)	0.0038 (17)	−0.0009 (17)
C18	0.036 (2)	0.031 (2)	0.030 (2)	0.0029 (17)	−0.0019 (18)	−0.0036 (18)
C19	0.043 (3)	0.028 (2)	0.048 (3)	0.0004 (18)	0.003 (2)	−0.0043 (19)
C20	0.039 (3)	0.052 (3)	0.067 (3)	0.009 (2)	−0.002 (2)	−0.016 (2)
C21	0.049 (3)	0.045 (3)	0.064 (3)	−0.004 (2)	0.013 (2)	−0.009 (2)
C22	0.065 (3)	0.048 (3)	0.053 (3)	−0.004 (3)	0.000 (3)	0.003 (2)
C23	0.088 (4)	0.051 (3)	0.046 (3)	0.004 (3)	−0.007 (3)	−0.005 (2)

Geometric parameters (Å, º) top

Cu1—O4ⁱ	1.929 (3)	C7—H7	0.9300
Cu1—O1	1.939 (3)	C8—C9	1.371 (6)
Cu1—N1	2.024 (3)	C8—H8	0.9300
Cu1—N2	2.025 (3)	C9—C10	1.394 (6)
Cu1—N4	2.829 (3)	C9—H9	0.9300
O1—C1	1.292 (5)	C10—C18	1.400 (5)
O2—C1	1.214 (5)	C10—C11	1.448 (6)
O3—C5	1.380 (4)	C11—C12	1.349 (6)
O3—C2	1.380 (5)	C11—H11	0.9300
O4—C6	1.284 (5)	C12—C13	1.431 (6)
O4—Cu1ⁱⁱ	1.929 (3)	C12—H12	0.9300
O5—C6	1.228 (5)	C13—C14	1.402 (6)
O6—C19	1.213 (5)	C13—C17	1.410 (5)
N1—C7	1.321 (5)	C14—C15	1.371 (6)
N1—C18	1.366 (5)	C14—H14	0.9300
N2—C16	1.323 (5)	C15—C16	1.405 (6)
N2—C17	1.369 (5)	C15—H15	0.9300
N3—C19	1.360 (5)	C16—H16	0.9300
N3—C21	1.438 (5)	C17—C18	1.428 (6)
N3—C23	1.443 (5)	C20—C21	1.524 (6)
N4—C19	1.403 (5)	C20—H20A	0.9700
N4—C20	1.457 (5)	C20—H20B	0.9700
N4—C22	1.467 (5)	C21—H21A	0.9700
C1—C2	1.483 (5)	C21—H21B	0.9700
C2—C3	1.360 (6)	C22—H22A	0.9600
C3—C4	1.428 (5)	C22—H22B	0.9600
C3—H3	0.9300	C22—H22C	0.9600
C4—C5	1.363 (6)	C23—H23A	0.9600
C4—H4	0.9300	C23—H23B	0.9600
C5—C6	1.479 (5)	C23—H23C	0.9600
C7—C8	1.412 (6)

O4ⁱ—Cu1—O1	91.66 (12)	C9—C10—C18	117.6 (4)
O4ⁱ—Cu1—N1	93.94 (12)	C9—C10—C11	124.2 (4)
O1—Cu1—N1	169.56 (12)	C18—C10—C11	118.1 (4)
O4ⁱ—Cu1—N2	174.20 (13)	C12—C11—C10	121.5 (4)
O1—Cu1—N2	93.14 (12)	C12—C11—H11	119.3
N1—Cu1—N2	81.83 (13)	C10—C11—H11	119.3
O4ⁱ—Cu1—N4	91.21 (11)	C11—C12—C13	121.2 (4)
O1—Cu1—N4	81.19 (11)	C11—C12—H12	119.4
N1—Cu1—N4	89.88 (11)	C13—C12—H12	119.4
N2—Cu1—N4	92.75 (11)	C14—C13—C17	116.7 (4)
C1—O1—Cu1	120.1 (3)	C14—C13—C12	124.8 (4)
C5—O3—C2	107.0 (3)	C17—C13—C12	118.5 (4)
C6—O4—Cu1ⁱⁱ	119.8 (3)	C15—C14—C13	120.1 (4)
C7—N1—C18	117.9 (3)	C15—C14—H14	119.9
C7—N1—Cu1	129.6 (3)	C13—C14—H14	119.9
C18—N1—Cu1	112.4 (3)	C14—C15—C16	119.1 (4)
C16—N2—C17	117.7 (4)	C14—C15—H15	120.5
C16—N2—Cu1	129.9 (3)	C16—C15—H15	120.5
C17—N2—Cu1	112.4 (3)	N2—C16—C15	123.1 (4)
C19—N3—C21	111.8 (4)	N2—C16—H16	118.5
C19—N3—C23	122.3 (4)	C15—C16—H16	118.5
C21—N3—C23	123.4 (4)	N2—C17—C13	123.3 (4)
C19—N4—C20	108.2 (3)	N2—C17—C18	116.4 (4)
C19—N4—C22	118.4 (4)	C13—C17—C18	120.4 (4)
C20—N4—C22	117.1 (4)	N1—C18—C10	123.0 (4)
C19—N4—Cu1	103.4 (2)	N1—C18—C17	116.8 (3)
C20—N4—Cu1	109.3 (3)	C10—C18—C17	120.2 (4)
C22—N4—Cu1	98.7 (2)	O6—C19—N3	126.3 (4)
O2—C1—O1	125.9 (4)	O6—C19—N4	125.4 (4)
O2—C1—C2	122.0 (4)	N3—C19—N4	108.4 (4)
O1—C1—C2	112.1 (4)	N4—C20—C21	103.2 (4)
C3—C2—O3	109.9 (4)	N4—C20—H20A	111.1
C3—C2—C1	132.9 (4)	C21—C20—H20A	111.1
O3—C2—C1	117.2 (4)	N4—C20—H20B	111.1
C2—C3—C4	106.5 (4)	C21—C20—H20B	111.1
C2—C3—H3	126.7	H20A—C20—H20B	109.1
C4—C3—H3	126.7	N3—C21—C20	102.7 (4)
C5—C4—C3	107.2 (4)	N3—C21—H21A	111.2
C5—C4—H4	126.4	C20—C21—H21A	111.2
C3—C4—H4	126.4	N3—C21—H21B	111.2
C4—C5—O3	109.3 (3)	C20—C21—H21B	111.2
C4—C5—C6	132.6 (4)	H21A—C21—H21B	109.1
O3—C5—C6	118.0 (4)	N4—C22—H22A	109.5
O5—C6—O4	126.3 (4)	N4—C22—H22B	109.5
O5—C6—C5	121.3 (4)	H22A—C22—H22B	109.5
O4—C6—C5	112.4 (4)	N4—C22—H22C	109.5
N1—C7—C8	122.7 (4)	H22A—C22—H22C	109.5
N1—C7—H7	118.7	H22B—C22—H22C	109.5
C8—C7—H7	118.7	N3—C23—H23A	109.5
C9—C8—C7	118.9 (4)	N3—C23—H23B	109.5
C9—C8—H8	120.5	H23A—C23—H23B	109.5
C7—C8—H8	120.5	N3—C23—H23C	109.5
C8—C9—C10	119.8 (4)	H23A—C23—H23C	109.5
C8—C9—H9	120.1	H23B—C23—H23C	109.5
C10—C9—H9	120.1

O4ⁱ—Cu1—O1—C1	93.0 (3)	Cu1—N1—C7—C8	−178.5 (3)
N1—Cu1—O1—C1	−144.6 (6)	N1—C7—C8—C9	−3.5 (7)
N2—Cu1—O1—C1	−83.8 (3)	C7—C8—C9—C10	0.6 (7)
N4—Cu1—O1—C1	−176.1 (3)	C8—C9—C10—C18	2.2 (6)
O4ⁱ—Cu1—N1—C7	2.9 (4)	C8—C9—C10—C11	−176.6 (4)
O1—Cu1—N1—C7	−119.4 (7)	C9—C10—C11—C12	−179.3 (4)
N2—Cu1—N1—C7	178.9 (4)	C18—C10—C11—C12	2.0 (6)
N4—Cu1—N1—C7	−88.3 (4)	C10—C11—C12—C13	1.4 (7)
O4ⁱ—Cu1—N1—C18	−178.8 (3)	C11—C12—C13—C14	176.9 (4)
O1—Cu1—N1—C18	58.9 (8)	C11—C12—C13—C17	−3.1 (6)
N2—Cu1—N1—C18	−2.8 (3)	C17—C13—C14—C15	0.7 (6)
N4—Cu1—N1—C18	90.0 (3)	C12—C13—C14—C15	−179.3 (4)
O1—Cu1—N2—C16	10.7 (4)	C13—C14—C15—C16	−1.6 (6)
N1—Cu1—N2—C16	−178.5 (4)	C17—N2—C16—C15	1.1 (6)
N4—Cu1—N2—C16	92.0 (4)	Cu1—N2—C16—C15	−176.3 (3)
O1—Cu1—N2—C17	−166.8 (3)	C14—C15—C16—N2	0.7 (7)
N1—Cu1—N2—C17	4.0 (3)	C16—N2—C17—C13	−2.0 (6)
N4—Cu1—N2—C17	−85.5 (3)	Cu1—N2—C17—C13	175.8 (3)
O4ⁱ—Cu1—N4—C19	−97.5 (3)	C16—N2—C17—C18	177.6 (4)
O1—Cu1—N4—C19	171.0 (3)	Cu1—N2—C17—C18	−4.5 (4)
N1—Cu1—N4—C19	−3.6 (3)	C14—C13—C17—N2	1.1 (6)
N2—Cu1—N4—C19	78.3 (3)	C12—C13—C17—N2	−178.9 (3)
O4ⁱ—Cu1—N4—C20	147.4 (3)	C14—C13—C17—C18	−178.5 (4)
O1—Cu1—N4—C20	55.9 (3)	C12—C13—C17—C18	1.5 (6)
N1—Cu1—N4—C20	−118.6 (3)	C7—N1—C18—C10	−0.2 (6)
N2—Cu1—N4—C20	−36.8 (3)	Cu1—N1—C18—C10	−178.8 (3)
O4ⁱ—Cu1—N4—C22	24.6 (3)	C7—N1—C18—C17	179.7 (4)
O1—Cu1—N4—C22	−66.9 (3)	Cu1—N1—C18—C17	1.2 (4)
N1—Cu1—N4—C22	118.5 (3)	C9—C10—C18—N1	−2.4 (6)
N2—Cu1—N4—C22	−159.7 (3)	C11—C10—C18—N1	176.4 (4)
Cu1—O1—C1—O2	8.0 (5)	C9—C10—C18—C17	177.6 (4)
Cu1—O1—C1—C2	−172.7 (2)	C11—C10—C18—C17	−3.6 (6)
C5—O3—C2—C3	−0.4 (4)	N2—C17—C18—N1	2.3 (5)
C5—O3—C2—C1	179.2 (3)	C13—C17—C18—N1	−178.1 (3)
O2—C1—C2—C3	−176.7 (4)	N2—C17—C18—C10	−177.8 (3)
O1—C1—C2—C3	4.0 (6)	C13—C17—C18—C10	1.9 (6)
O2—C1—C2—O3	3.8 (5)	C21—N3—C19—O6	−177.5 (4)
O1—C1—C2—O3	−175.5 (3)	C23—N3—C19—O6	−14.8 (7)
O3—C2—C3—C4	0.2 (5)	C21—N3—C19—N4	1.1 (5)
C1—C2—C3—C4	−179.3 (4)	C23—N3—C19—N4	163.8 (4)
C2—C3—C4—C5	0.0 (5)	C20—N4—C19—O6	−166.9 (4)
C3—C4—C5—O3	−0.3 (5)	C22—N4—C19—O6	−30.6 (6)
C3—C4—C5—C6	−177.4 (4)	Cu1—N4—C19—O6	77.2 (4)
C2—O3—C5—C4	0.4 (4)	C20—N4—C19—N3	14.4 (4)
C2—O3—C5—C6	178.0 (3)	C22—N4—C19—N3	150.8 (4)
Cu1ⁱⁱ—O4—C6—O5	−3.8 (5)	Cu1—N4—C19—N3	−101.4 (3)
Cu1ⁱⁱ—O4—C6—C5	175.0 (2)	C19—N4—C20—C21	−22.9 (4)
C4—C5—C6—O5	174.0 (4)	C22—N4—C20—C21	−159.9 (4)
O3—C5—C6—O5	−2.8 (5)	Cu1—N4—C20—C21	89.0 (3)
C4—C5—C6—O4	−4.8 (6)	C19—N3—C21—C20	−15.0 (5)
O3—C5—C6—O4	178.3 (3)	C23—N3—C21—C20	−177.5 (4)
C18—N1—C7—C8	3.2 (6)	N4—C20—C21—N3	22.3 (4)

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

Experimental details

Crystal data
Chemical formula	[Cu(C₆H₂O₅)(C₁₂H₈N₂)(C₅H₁₀N₂O)]
M_r	511.98
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	293
a, b, c (Å)	15.620 (3), 14.598 (3), 18.616 (4)
V (Å³)	4244.8 (15)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	1.08
Crystal size (mm)	0.10 × 0.10 × 0.10

Data collection
Diffractometer	Rigaku R-AXIS RAPID diffractometer
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995)
T_min, T_max	0.900, 0.900
No. of measured, independent and observed [I > 2σ(I)] reflections	30193, 3727, 2376
R_int	0.110
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.109, 1.04
No. of reflections	3727
No. of parameters	309
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.46, −0.37

Computer programs: PROCESS-AUTO (Rigaku, 1998), CrystalStructure (Rigaku/MSC, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg, 2000).

Acknowledgements

This project was sponsored by the Scientific Research Foundation for the Returned Overseas Team, Chinese Education Ministry.

References

Brandenburg, K. (2000). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan. Google Scholar
Li, Y.-F., Gao, Y., Xu, Y., Qin, X. & Gao, W.-Y. (2012a). Acta Cryst. E68, m445. CSD CrossRef IUCr Journals Google Scholar
Li, Y.-F., Gao, Y., Xu, Y., Qin, X.-L. & Gao, W.-Y. (2012b). Acta Cryst. E68, m500. CSD CrossRef IUCr Journals Google Scholar
Rigaku (1998). PROCESS-AUTO. Rigaku Corporation, Tokyo, Japan. Google Scholar
Rigaku/MSC (2002). CrystalStructure. Rigaku/MSC Inc., The Woodlands, Texas, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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