A new copper(II) complex based on 1-[(1H-benzotriazol-1-yl)meth­yl]-1H-1,2,4-triazole

Yang, H.; Zhang, J.; Zhao, D.

doi:10.1107/S1600536811013511

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 5| May 2011| Page m602

doi:10.1107/S1600536811013511

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A new copper(II) complex based on 1-[(1H-benzotriazol-1-yl)methyl]-1H-1,2,4-triazole

Huai-xia Yang,^a ^* Jun Zhang ^b and Dong Zhao ^b

^aPharmacy College, Henan University of Traditional Chinese Medicine, Zhengzhou 450008, People's Republic of China, and ^bDepartment of Chemistry, Zhengzhou University, Zhengzhou 450052, People's Republic of China
^*Correspondence e-mail: yanghuaixia888@163.com

(Received 16 March 2011; accepted 11 April 2011; online 16 April 2011)

The title complex, tetraaqua{1-[(1H-benzotriazol-1-yl)methyl]-1H-1,2,4-triazole-κN⁴}(sulfato-κO)copper(II) sesquihydrate, [Cu(SO₄)(C₉H₈N₆)(H₂O)₄]·1.5H₂O, is composed of one copper atom, one 1-[(2H-benzotriazol-1-yl)methyl]-1-H-1,2,4-triazole (bmt) ligand, one sulfate ligand, four coordinated water molecules and one and a half uncoordinated water molecules. The Cu^II atom is six-coordinated by one N atom from a bmt ligand and five O atoms from the monodentate sulfate ligand and four water molecules in a distorted octahedral geometry. In the crystal, adjacent molecules are linked through O—H⋯O and O—H⋯N hydrogen bonds involving the sulfate anion and the coordinated and uncoordinated water molecules into a three-dimensional network.

Related literature

For background to complexes based on triazole and benzotriazole derivatives, see: Aromia et al. (2011 ); Meng et al. (2009 ). For background to complexes with Cu^II atoms, see: Zhou et al. (2007 ); Brown et al. (2009 ).

Experimental

Crystal data

[Cu(SO₄)(C₉H₈N₆)(H₂O)₄]·1.5H₂O
M_r = 458.90
Monoclinic, C 2/c
a = 12.496 (3) Å
b = 8.662 (2) Å
c = 31.543 (6) Å
β = 90.97 (3)°
V = 3413.7 (12) Å³
Z = 8
Mo Kα radiation
μ = 1.47 mm⁻¹
T = 293 K
0.20 × 0.16 × 0.15 mm

Data collection

Rigaku Saturn diffractometer
Absorption correction: multi-scan (CrystalClear, Rigaku/MSC, 2006 ) T_min = 0.758, T_max = 0.810
13448 measured reflections
4046 independent reflections
3502 reflections with I > 2σ(I)
R_int = 0.035

Refinement

R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.088
S = 1.10
4046 reflections
240 parameters
H-atom parameters constrained
Δρ_max = 0.33 e Å⁻³
Δρ_min = −0.45 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1W⋯O9	0.85	1.82	2.662 (3)	170
O2—H3W⋯O10ⁱ	0.85	1.89	2.723 (2)	165
O9—H9W⋯N6ⁱⁱ	0.85	2.00	2.836 (3)	168
O10—H11W⋯O6ⁱⁱⁱ	0.85	1.93	2.771 (2)	170
O1—H2W⋯N2ⁱⁱⁱ	0.85	2.16	2.951 (3)	155
O3—H5W⋯O8^iv	0.85	1.99	2.789 (3)	156
O4—H7W⋯O6^v	0.85	1.86	2.697 (2)	170
O9—H10W⋯O7^v	0.85	1.99	2.824 (3)	165
O3—H6W⋯O6^v	0.85	2.19	2.943 (3)	148
O2—H4W⋯O5^vi	0.85	1.92	2.766 (2)	174
O4—H8W⋯O8^vi	0.85	1.85	2.702 (2)	175
Symmetry codes: (i) $[x+{\script{1\over 2}}, y-{\script{1\over 2}}, z]$ ; (ii) $[-x+{\script{3\over 2}}, -y+{\script{1\over 2}}, -z+1]$ ; (iii) $[x-{\script{1\over 2}}, y+{\script{1\over 2}}, z]$ ; (iv) x, y-1, z; (v) $[x-{\script{1\over 2}}, y-{\script{1\over 2}}, z]$ ; (vi) $[-x+{\script{3\over 2}}, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Data collection: CrystalClear (Rigaku/MSC, 2006); 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 global, I. DOI: 10.1107/S1600536811013511/bv2183sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811013511/bv2183Isup2.hkl

checkCIF report

Comment top

Triazole and benzotriazole derivatives have been widely used in the construction of complexes since they can act as polydentate ligands and function as bridging ligands (Aromia et al., 2011; Meng et al., 2009). Moreover, Cu^II complexes have attracted more and more attention owing to their intrinsic esthetic appeal and potential applications in various fields (Zhou et al., 2007; Brown et al., 2009). In this work, through the reaction of 1-((benzotriazol-1-yl)methyl)-1-H-1,2,4-triazole (bmt) with copper sulfate at room temperature, we obtained the title complex [Cu(bmt) (SO₄) (H₂O)₄] (H₂O)_1.5, which is reported here. As shown in Figure 1, each Cu^II ion is located in a slightly distorted octahedral environment and is coordinated to one nitrogen atom from the bmt ligand, five oxygen atoms from four water molecules and one monodentate sulfate. Atoms O1, O2, O4, N1 and Cu1 are nearly co-planar (the mean deviation from the plane is 0.0203 Å). The apical Cu1—O3 and Cu1—O5 bond lengths (2.331 (2) and 2.465 Å) are considerably longer than the equatorial ones (1.974 (2)- 2.002 (2) Å) due to the Jahn-Teller effect. Intramolecular O—H···O hydrogen bonds stabilize the molecular configuration and O—H···O, O—H···N hydrogen bonds between adjacent molecules consolidate the crystal packing.

Related literature top

For background to complexes based on triazole and benzotriazole derivatives, see: Aromia et al. (2011); Meng et al. (2009). For background complexes with Cu^II atoms, see: Zhou et al. (2007); Brown et al. (2009).

Experimental top

The ligand 1-((benzotriazol-1-yl)methyl)-1-H-1,2,4-triazole (0.1 mmol) in methanol (4 ml) was added dropwise to an aqueous solution (2 ml) of copper sulfate (0.1 mmol). The resulting solution was allowed to stand at room temperature. After three weeks blue crystals with good quality were obtained from the filtrate and dried in air.

Computing details top

Data collection: CrystalClear (Rigaku/MSC, 2006); cell refinement: CrystalClear (Rigaku/MSC, 2006); data reduction: CrystalClear (Rigaku/MSC, 2006); program(s) used to solve structure: SHELXL97 (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. View of the title complex, showing the labeling of the 30% probability ellipsoids. H atoms are omitted for clarity.

tetraaqua{1-[(1H-benzotriazol-1-yl)methyl]-1H-1,2,4-triazole- κN⁴}(sulfato-κO)copper(II) sesquihydrate top

Crystal data top

[Cu(SO₄)(C₉H₈N₆)(H₂O)₄]·1.5H₂O	F(000) = 1888
M_r = 458.90	D_x = 1.786 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 4587 reflections
a = 12.496 (3) Å	θ = 2.6–27.9°
b = 8.662 (2) Å	µ = 1.47 mm⁻¹
c = 31.543 (6) Å	T = 293 K
β = 90.97 (3)°	Prism, blue
V = 3413.7 (12) Å³	0.20 × 0.16 × 0.15 mm
Z = 8

Data collection top

Rigaku Saturn diffractometer	4046 independent reflections
Radiation source: fine-focus sealed tube	3502 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.035
Detector resolution: 28.5714 pixels mm^-1	θ_max = 27.9°, θ_min = 2.6°
ω scans	h = −16→16
Absorption correction: multi-scan (CrystalClear, Rigaku/MSC, 2006)	k = −8→11
T_min = 0.758, T_max = 0.810	l = −41→36
13448 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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.088	H-atom parameters constrained
S = 1.10	w = 1/[σ²(F_o²) + (0.0387P)² + 1.547P] where P = (F_o² + 2F_c²)/3
4046 reflections	(Δ/σ)_max = 0.003
240 parameters	Δρ_max = 0.33 e Å⁻³
0 restraints	Δρ_min = −0.45 e Å⁻³

Crystal data top

[Cu(SO₄)(C₉H₈N₆)(H₂O)₄]·1.5H₂O	V = 3413.7 (12) Å³
M_r = 458.90	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 12.496 (3) Å	µ = 1.47 mm⁻¹
b = 8.662 (2) Å	T = 293 K
c = 31.543 (6) Å	0.20 × 0.16 × 0.15 mm
β = 90.97 (3)°

Data collection top

Rigaku Saturn diffractometer	4046 independent reflections
Absorption correction: multi-scan (CrystalClear, Rigaku/MSC, 2006)	3502 reflections with I > 2σ(I)
T_min = 0.758, T_max = 0.810	R_int = 0.035
13448 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	0 restraints
wR(F²) = 0.088	H-atom parameters constrained
S = 1.10	Δρ_max = 0.33 e Å⁻³
4046 reflections	Δρ_min = −0.45 e Å⁻³
240 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	0.76191 (2)	0.23448 (3)	0.685956 (9)	0.02244 (10)
N1	0.90110 (15)	0.1958 (2)	0.65733 (6)	0.0239 (4)
N2	1.05863 (17)	0.0889 (2)	0.64129 (7)	0.0300 (5)
N3	1.04251 (15)	0.2230 (2)	0.61944 (6)	0.0220 (4)
N4	1.10175 (16)	0.2341 (2)	0.54782 (6)	0.0247 (4)
N5	1.02130 (17)	0.3031 (3)	0.52517 (7)	0.0332 (5)
N6	1.01910 (18)	0.2435 (3)	0.48737 (7)	0.0349 (5)
O1	0.70071 (13)	0.31913 (19)	0.63234 (5)	0.0274 (4)
H1W	0.6484	0.2655	0.6231	0.033*
H2W	0.6787	0.4113	0.6352	0.033*
O2	0.82932 (13)	0.1504 (2)	0.73862 (5)	0.0296 (4)
H3W	0.8809	0.2075	0.7469	0.036*
H4W	0.7954	0.1060	0.7583	0.036*
O3	0.69989 (14)	−0.0117 (2)	0.66866 (6)	0.0377 (5)
H5W	0.7299	−0.0835	0.6829	0.045*
H6W	0.6351	−0.0260	0.6755	0.045*
O4	0.62735 (13)	0.28272 (19)	0.71502 (5)	0.0262 (4)
H7W	0.5760	0.2261	0.7063	0.031*
H8W	0.6359	0.2859	0.7418	0.031*
O5	0.79519 (13)	0.50995 (19)	0.70084 (5)	0.0294 (4)
O6	0.97927 (13)	0.5740 (2)	0.68985 (5)	0.0306 (4)
O7	0.84885 (15)	0.6278 (2)	0.63497 (5)	0.0325 (4)
O8	0.84941 (15)	0.77569 (18)	0.69968 (5)	0.0304 (4)
O9	0.54758 (15)	0.1536 (2)	0.59423 (5)	0.0363 (4)
H9W	0.5344	0.1744	0.5683	0.044*
H10W	0.4907	0.1616	0.6085	0.044*
O10	0.5000	0.8423 (3)	0.7500	0.0351 (6)
H11W	0.4932	0.9044	0.7293	0.042*
C1	0.94835 (18)	0.2833 (3)	0.62931 (7)	0.0237 (5)
H1A	0.9201	0.3741	0.6180	0.028*
C2	0.9720 (2)	0.0775 (3)	0.66390 (8)	0.0304 (6)
H2A	0.9598	−0.0033	0.6826	0.036*
C3	1.1218 (2)	0.2839 (3)	0.59085 (7)	0.0271 (5)
H3A	1.1207	0.3958	0.5920	0.033*
H3B	1.1924	0.2496	0.6000	0.033*
C4	1.15259 (19)	0.1279 (3)	0.52359 (7)	0.0245 (5)
C5	1.0988 (2)	0.1353 (3)	0.48467 (8)	0.0280 (5)
C6	1.1307 (2)	0.0434 (3)	0.45077 (8)	0.0380 (7)
H6A	1.0950	0.0472	0.4247	0.046*
C7	1.2158 (2)	−0.0516 (3)	0.45735 (10)	0.0442 (7)
H7A	1.2385	−0.1144	0.4353	0.053*
C8	1.2701 (2)	−0.0572 (3)	0.49644 (10)	0.0433 (7)
H8A	1.3287	−0.1227	0.4995	0.052*
C9	1.2399 (2)	0.0309 (3)	0.53082 (9)	0.0340 (6)
H9A	1.2755	0.0258	0.5569	0.041*
S1	0.86691 (4)	0.62224 (6)	0.680761 (18)	0.02084 (14)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.01695 (15)	0.03034 (19)	0.02010 (17)	−0.00004 (11)	0.00198 (11)	0.00009 (11)
N1	0.0208 (10)	0.0252 (11)	0.0259 (11)	0.0019 (8)	0.0041 (8)	0.0001 (8)
N2	0.0281 (11)	0.0278 (11)	0.0344 (13)	0.0062 (9)	0.0069 (9)	0.0071 (9)
N3	0.0216 (10)	0.0235 (10)	0.0208 (10)	0.0011 (8)	0.0032 (8)	0.0011 (8)
N4	0.0216 (10)	0.0311 (11)	0.0215 (11)	0.0046 (8)	0.0014 (8)	0.0020 (8)
N5	0.0289 (12)	0.0416 (13)	0.0292 (12)	0.0109 (10)	0.0005 (9)	0.0034 (10)
N6	0.0296 (12)	0.0479 (14)	0.0270 (12)	0.0077 (10)	−0.0029 (9)	0.0014 (10)
O1	0.0290 (9)	0.0262 (9)	0.0270 (9)	0.0039 (7)	−0.0024 (7)	−0.0009 (7)
O2	0.0226 (9)	0.0409 (11)	0.0252 (9)	−0.0061 (7)	0.0014 (7)	0.0041 (8)
O3	0.0296 (10)	0.0339 (11)	0.0494 (12)	−0.0008 (8)	−0.0039 (9)	−0.0045 (9)
O4	0.0200 (8)	0.0334 (9)	0.0252 (9)	−0.0042 (7)	0.0025 (7)	−0.0016 (7)
O5	0.0286 (9)	0.0254 (9)	0.0345 (10)	−0.0078 (7)	0.0075 (8)	−0.0030 (7)
O6	0.0190 (8)	0.0371 (10)	0.0355 (11)	−0.0002 (7)	−0.0033 (7)	0.0005 (8)
O7	0.0344 (10)	0.0431 (11)	0.0197 (9)	0.0051 (8)	−0.0020 (7)	0.0007 (8)
O8	0.0414 (11)	0.0213 (9)	0.0285 (10)	−0.0001 (7)	0.0031 (8)	−0.0014 (7)
O9	0.0346 (10)	0.0515 (12)	0.0228 (10)	0.0007 (9)	−0.0018 (8)	0.0052 (8)
O10	0.0373 (15)	0.0287 (14)	0.0387 (16)	0.000	−0.0132 (12)	0.000
C1	0.0227 (12)	0.0253 (12)	0.0230 (12)	0.0054 (9)	0.0028 (9)	0.0014 (10)
C2	0.0293 (13)	0.0261 (13)	0.0362 (15)	0.0037 (10)	0.0091 (11)	0.0080 (11)
C3	0.0259 (12)	0.0323 (14)	0.0234 (13)	−0.0025 (10)	0.0042 (10)	0.0004 (10)
C4	0.0232 (12)	0.0266 (13)	0.0240 (13)	0.0002 (9)	0.0045 (9)	0.0018 (10)
C5	0.0265 (13)	0.0324 (14)	0.0251 (14)	−0.0007 (10)	0.0010 (10)	0.0025 (10)
C6	0.0394 (16)	0.0489 (17)	0.0257 (15)	−0.0065 (13)	0.0023 (12)	−0.0080 (12)
C7	0.0467 (18)	0.0411 (17)	0.0453 (19)	−0.0024 (14)	0.0146 (14)	−0.0121 (14)
C8	0.0323 (16)	0.0386 (17)	0.059 (2)	0.0095 (12)	0.0086 (14)	−0.0033 (14)
C9	0.0267 (13)	0.0375 (15)	0.0376 (16)	0.0063 (11)	−0.0033 (11)	0.0043 (12)
S1	0.0193 (3)	0.0228 (3)	0.0205 (3)	−0.0010 (2)	0.0009 (2)	−0.0003 (2)

Geometric parameters (Å, º) top

Cu1—O4	1.974 (2)	O4—H8W	0.8505
Cu1—O1	1.985 (2)	O5—S1	1.473 (2)
Cu1—O2	1.988 (2)	O6—S1	1.488 (2)
Cu1—N1	2.002 (2)	O7—S1	1.459 (2)
Cu1—O3	2.331 (2)	O8—S1	1.475 (2)
N1—C1	1.312 (3)	O9—H9W	0.8501
N1—C2	1.368 (3)	O9—H10W	0.8499
N2—C2	1.310 (3)	O10—H11W	0.8500
N2—N3	1.363 (3)	C1—H1A	0.9300
N3—C1	1.329 (3)	C2—H2A	0.9300
N3—C3	1.451 (3)	C3—H3A	0.9700
N4—C4	1.360 (3)	C3—H3B	0.9700
N4—N5	1.362 (3)	C4—C5	1.391 (3)
N4—C3	1.442 (3)	C4—C9	1.393 (3)
N5—N6	1.299 (3)	C5—C6	1.397 (3)
N6—C5	1.372 (3)	C6—C7	1.358 (4)
O1—H1W	0.8501	C6—H6A	0.9300
O1—H2W	0.8499	C7—C8	1.398 (4)
O2—H3W	0.8501	C7—H7A	0.9300
O2—H4W	0.8499	C8—C9	1.384 (4)
O3—H5W	0.8499	C8—H8A	0.9300
O3—H6W	0.8500	C9—H9A	0.9300
O4—H7W	0.8499

O4—Cu1—O1	89.92 (7)	N1—C1—H1A	125.0
O4—Cu1—O2	92.39 (7)	N3—C1—H1A	125.0
O1—Cu1—O2	177.58 (7)	N2—C2—N1	113.6 (2)
O4—Cu1—N1	177.18 (7)	N2—C2—H2A	123.2
O1—Cu1—N1	90.16 (8)	N1—C2—H2A	123.2
O2—Cu1—N1	87.50 (8)	N4—C3—N3	111.5 (2)
O4—Cu1—O3	91.14 (7)	N4—C3—H3A	109.3
O1—Cu1—O3	90.96 (7)	N3—C3—H3A	109.3
O2—Cu1—O3	89.72 (7)	N4—C3—H3B	109.3
N1—Cu1—O3	91.67 (7)	N3—C3—H3B	109.3
C1—N1—C2	103.7 (2)	H3A—C3—H3B	108.0
C1—N1—Cu1	127.68 (16)	N4—C4—C5	104.0 (2)
C2—N1—Cu1	128.52 (16)	N4—C4—C9	133.5 (2)
C2—N2—N3	102.88 (19)	C5—C4—C9	122.5 (2)
C1—N3—N2	109.89 (19)	N6—C5—C4	108.5 (2)
C1—N3—C3	128.3 (2)	N6—C5—C6	130.8 (2)
N2—N3—C3	121.84 (19)	C4—C5—C6	120.6 (2)
C4—N4—N5	110.47 (19)	C7—C6—C5	117.5 (3)
C4—N4—C3	131.0 (2)	C7—C6—H6A	121.3
N5—N4—C3	118.5 (2)	C5—C6—H6A	121.3
N6—N5—N4	108.1 (2)	C6—C7—C8	121.5 (3)
N5—N6—C5	108.9 (2)	C6—C7—H7A	119.2
Cu1—O1—H1W	112.0	C8—C7—H7A	119.2
Cu1—O1—H2W	112.2	C9—C8—C7	122.5 (3)
H1W—O1—H2W	107.5	C9—C8—H8A	118.8
Cu1—O2—H3W	110.6	C7—C8—H8A	118.8
Cu1—O2—H4W	124.5	C8—C9—C4	115.3 (3)
H3W—O2—H4W	115.1	C8—C9—H9A	122.3
Cu1—O3—H5W	113.8	C4—C9—H9A	122.3
Cu1—O3—H6W	112.8	O7—S1—O5	111.25 (11)
H5W—O3—H6W	100.0	O7—S1—O8	110.46 (10)
Cu1—O4—H7W	111.9	O5—S1—O8	109.00 (10)
Cu1—O4—H8W	112.0	O7—S1—O6	109.24 (11)
H7W—O4—H8W	114.9	O5—S1—O6	108.10 (11)
H9W—O9—H10W	109.9	O8—S1—O6	108.73 (11)
N1—C1—N3	109.9 (2)

O4—Cu1—N1—C1	−53.0 (16)	N5—N4—C3—N3	76.2 (3)
O1—Cu1—N1—C1	38.7 (2)	C1—N3—C3—N4	−87.7 (3)
O2—Cu1—N1—C1	−140.7 (2)	N2—N3—C3—N4	93.6 (3)
O3—Cu1—N1—C1	129.7 (2)	N5—N4—C4—C5	−0.1 (3)
O4—Cu1—N1—C2	123.1 (14)	C3—N4—C4—C5	−178.0 (2)
O1—Cu1—N1—C2	−145.3 (2)	N5—N4—C4—C9	177.9 (3)
O2—Cu1—N1—C2	35.3 (2)	C3—N4—C4—C9	−0.1 (5)
O3—Cu1—N1—C2	−54.3 (2)	N5—N6—C5—C4	0.4 (3)
C2—N2—N3—C1	−0.8 (3)	N5—N6—C5—C6	−178.1 (3)
C2—N2—N3—C3	178.1 (2)	N4—C4—C5—N6	−0.2 (3)
C4—N4—N5—N6	0.3 (3)	C9—C4—C5—N6	−178.4 (2)
C3—N4—N5—N6	178.5 (2)	N4—C4—C5—C6	178.5 (2)
N4—N5—N6—C5	−0.4 (3)	C9—C4—C5—C6	0.3 (4)
C2—N1—C1—N3	−0.3 (3)	N6—C5—C6—C7	178.1 (3)
Cu1—N1—C1—N3	176.54 (15)	C4—C5—C6—C7	−0.3 (4)
N2—N3—C1—N1	0.7 (3)	C5—C6—C7—C8	−0.3 (4)
C3—N3—C1—N1	−178.1 (2)	C6—C7—C8—C9	1.1 (5)
N3—N2—C2—N1	0.7 (3)	C7—C8—C9—C4	−1.0 (4)
C1—N1—C2—N2	−0.3 (3)	N4—C4—C9—C8	−177.2 (3)
Cu1—N1—C2—N2	−177.05 (17)	C5—C4—C9—C8	0.4 (4)
C4—N4—C3—N3	−106.0 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1W···O9	0.85	1.82	2.662 (3)	170
O2—H3W···O10ⁱ	0.85	1.89	2.723 (2)	165
O9—H9W···N6ⁱⁱ	0.85	2.00	2.836 (3)	168
O10—H11W···O6ⁱⁱⁱ	0.85	1.93	2.771 (2)	170
O10—H11W···S1ⁱⁱⁱ	0.85	2.88	3.6458 (18)	150
O1—H2W···N2ⁱⁱⁱ	0.85	2.16	2.951 (3)	155
O3—H5W···O8^iv	0.85	1.99	2.789 (3)	156
O4—H7W···O6^v	0.85	1.86	2.697 (2)	170
O4—H7W···S1^v	0.85	2.87	3.6842 (19)	162
O9—H10W···O7^v	0.85	1.99	2.824 (3)	165
O9—H10W···S1^v	0.85	2.80	3.582 (2)	154
O3—H6W···O6^v	0.85	2.19	2.943 (3)	148
O2—H4W···O5^vi	0.85	1.92	2.766 (2)	174
O2—H4W···S1^vi	0.85	2.82	3.571 (2)	148
O4—H8W···O8^vi	0.85	1.85	2.702 (2)	175
O4—H8W···S1^vi	0.85	2.82	3.5687 (18)	147

Symmetry codes: (i) x+1/2, y−1/2, z; (ii) −x+3/2, −y+1/2, −z+1; (iii) x−1/2, y+1/2, z; (iv) x, y−1, z; (v) x−1/2, y−1/2, z; (vi) −x+3/2, y−1/2, −z+3/2.

Experimental details

Crystal data
Chemical formula	[Cu(SO₄)(C₉H₈N₆)(H₂O)₄]·1.5H₂O
M_r	458.90
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	293
a, b, c (Å)	12.496 (3), 8.662 (2), 31.543 (6)
β (°)	90.97 (3)
V (Å³)	3413.7 (12)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	1.47
Crystal size (mm)	0.20 × 0.16 × 0.15

Data collection
Diffractometer	Rigaku Saturn diffractometer
Absorption correction	Multi-scan (CrystalClear, Rigaku/MSC, 2006)
T_min, T_max	0.758, 0.810
No. of measured, independent and observed [I > 2σ(I)] reflections	13448, 4046, 3502
R_int	0.035
(sin θ/λ)_max (Å⁻¹)	0.658

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.088, 1.10
No. of reflections	4046
No. of parameters	240
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.33, −0.45

Computer programs: CrystalClear (Rigaku/MSC, 2006), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1W···O9	0.85	1.82	2.662 (3)	170
O2—H3W···O10ⁱ	0.85	1.89	2.723 (2)	165
O9—H9W···N6ⁱⁱ	0.85	2.00	2.836 (3)	168
O10—H11W···O6ⁱⁱⁱ	0.85	1.93	2.771 (2)	170
O10—H11W···S1ⁱⁱⁱ	0.85	2.88	3.6458 (18)	150
O1—H2W···N2ⁱⁱⁱ	0.85	2.16	2.951 (3)	155
O3—H5W···O8^iv	0.85	1.99	2.789 (3)	156
O4—H7W···O6^v	0.85	1.86	2.697 (2)	170
O4—H7W···S1^v	0.85	2.87	3.6842 (19)	162
O9—H10W···O7^v	0.85	1.99	2.824 (3)	165
O9—H10W···S1^v	0.85	2.80	3.582 (2)	154
O3—H6W···O6^v	0.85	2.19	2.943 (3)	148
O2—H4W···O5^vi	0.85	1.92	2.766 (2)	174
O2—H4W···S1^vi	0.85	2.82	3.571 (2)	148
O4—H8W···O8^vi	0.85	1.85	2.702 (2)	175
O4—H8W···S1^vi	0.85	2.82	3.5687 (18)	147

Symmetry codes: (i) x+1/2, y−1/2, z; (ii) −x+3/2, −y+1/2, −z+1; (iii) x−1/2, y+1/2, z; (iv) x, y−1, z; (v) x−1/2, y−1/2, z; (vi) −x+3/2, y−1/2, −z+3/2.

Acknowledgements

The study was supported by the Science and Technology Department of Henan Province (082102330003).

References

Aromia, G., Barriosa, L. A., Roubeaub, O. & Gameza, P. (2011). Coord. Chem. Rev. 255, 485–564. Google Scholar
Brown, K., Zolezzi, S., Aguirre, P., Venegas-Yazigi, D., Paredes-Garcia, V., Baggio, R., Novak, M. A. & Spodine, E. (2009). Dalton Trans. pp. 1422–1427. CrossRef Google Scholar
Meng, X.-R., Jin, S.-Z., Hou, H.-W., Du, C.-X. & Ng, S. W. (2009). Inorg. Chim. Acta, 362, 1519–1527. CrossRef CAS Google Scholar
Rigaku/MSC (2006). CrystalClear. Rigaku/MSC, The Woodlands, Texas, USA, and Rigaku Corporation, Tokyo, Japan. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Zhou, X.-L., Meng, X.-R., Cheng, W., Hou, H.-W., Tang, M.-S. & Fan, Y.-T. (2007). Inorg. Chim. Acta, 360, 3467–3474. CrossRef CAS Google Scholar

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Volume 67| Part 5| May 2011| Page m602

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

A new copper(II) complex based on 1-[(1H-benzotriazol-1-yl)meth­yl]-1H-1,2,4-triazole

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

metal-organic compounds

A new copper(II) complex based on 1-[(1H-benzotriazol-1-yl)methyl]-1H-1,2,4-triazole