cis-Bis(butyl­amine-κN)bis­[sulfa­diazine(1−)-κ2N,N′]copper(II) penta­hydrate

Paşaoğlu, H.; Kaştaş, G.; Heren, Z.; Büyükgüngör, O.

doi:10.1107/S1600536808026457

metal-organic compounds

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ISSN: 2056-9890

Volume 64| Part 9| September 2008| Page m1192

doi:10.1107/S1600536808026457

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cis-Bis(butylamine-κN)bis[sulfadiazine(1−)-κ²N,N′]copper(II) pentahydrate

Hümeyra Paşaoğlu,^a Gökhan Kaştaş,^a ^* Zerrin Heren ^b and Orhan Büyükgüngör ^a

^aOndokuz Mayıs University, Department of Physics, Faculty of Arts and Sciences, 55139 Kurupelit Samsun, Turkey, and ^bOndokuz Mayıs University, Department of Chemistry, Faculty of Arts and Sciences, 55139 Kurupelit Samsun, Turkey
^*Correspondence e-mail: gkastas@omu.edu.tr

(Received 15 August 2008; accepted 17 August 2008; online 23 August 2008)

In the title compound {systematic name: cis-bis[4-amino-N-(pyrimidin-2-yl)benzenesulfonamidato-κ²N,N′]bis(butylamine-κN)copper(II) pentahydrate}, [Cu(C₁₀H₉N₄O₂S)₂(C₄H₁₁N)₂]·5H₂O or [Cu(sdz)₂(ba)₂]·5H₂O [ba is butylamine and sdz = sulfadiazine(1−)], the copper(II) cation is six-coordinated by four N atoms of two sulfadiazine ligands and two N atoms of butylamine ligands. The copper(II) ion and one of the water molecules lie on twofold rotation axes. One of the butyl groups is disordered over two sites, with occupancies of 0.395 (8) and 0.605 (8). The geometry around the S atom is distorted tetrahedral. The crystal structure involves intermolecular N—H⋯N and N—H⋯O hydrogen bonds. N—H⋯N hydrogen bonds between sdz ligands lead to a sheet structure parallel to the ab plane.

Related literature

For related structures, see: Heren et al. (2006 ); Chung et al. (1975 ).

Experimental

Crystal data

[Cu(C₁₀H₉N₄O₂S)₂(C₄H₁₁N)₂]·5H₂O
M_r = 790.04
Orthorhombic, P b c n
a = 22.623 (6) Å
b = 10.342 (5) Å
c = 16.250 (6) Å
V = 3802 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.74 mm⁻¹
T = 296 K
0.34 × 0.21 × 0.19 mm

Data collection

Stoe IPDS2 diffractometer
Absorption correction: integration (X-RED32; Stoe & Cie, 2002 ) T_min = 0.821, T_max = 0.899
57960 measured reflections
4235 independent reflections
2098 reflections with I > 2σ(I)
R_int = 0.085

Refinement

R[F² > 2σ(F²)] = 0.048
wR(F²) = 0.141
S = 0.90
4235 reflections
234 parameters
H-atom parameters constrained
Δρ_max = 0.65 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
N5—H5A⋯N2ⁱ	0.86	2.53	3.359 (5)	162
N4—H4A⋯O5ⁱⁱ	0.90	2.45	3.337 (6)	171
N4—H4B⋯O4ⁱⁱⁱ	0.90	2.25	3.119 (6)	161
N5—H5B⋯O5^iv	0.86	2.26	3.113 (5)	170
Symmetry codes: (i) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, z]$ ; (ii) $[x, -y+1, z-{\script{1\over 2}}]$ ; (iii) $[x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iv) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, z]$ .

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ) and Mercury (Macrae et al., 2006 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808026457/cf2216sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808026457/cf2216Isup2.hkl

checkCIF report

Comment top

In the title complex (I), the copper(II) ion is six-coordinated by four N atoms of sulfadiazine ligands and two N atoms of butylammonium ligands. The copper(II) ion and one of the water molecules lie on twofold rotation axes. It is found that the Cu–N_sdz and Cu–N_ba bond distances are nearly equal. The bond angles around the S atom correspond to a distorted tetrahedral geometry. The C4–N5 bond distance and the torsion angle C1–S1–N1–C7 are comparable to those observed in related structures (Heren et al., 2006; Chung et al., 1975). One of the butyl groups is disordered over two sites with occupancies of 0.395 (8):0.605 (8) (see Fig. 1).

The packing of (I) is stabilized by intermolecular N—H···N and N—H···O hydrogen bonds (Table 1). The N—H···N hydrogen bond takes place between sdz ligands and it is seen that these hydrogen bonds generate a sheet structure parallel to the ab plane (Fig. 2). The H atoms of water molecules could not be located from a Fourier map. However, it is possible to see that water molecules are involved in hydrogen bonds with sdz and ba ligands on the basis of interatomic distances.

Related literature top

For related structures, see: Heren et al. (2006); Chung et al. (1975).

Experimental top

A solution of butylamine (2 mmol) in ethanol (20 ml) was added dropwise with stirring to a solution of Cu(II) sulfadiazine (1 mmol) in methanol (40 ml). The solution was heated and stirred for 3 h at 343 K and then the mixture was cooled to room temperature. The blue crystals were filtered off, washed with cold distilled water and acetone, and dried in vacuo. Analysis calculated: C 42.62, H 5.84, N 17.76%; found: C 43.08, H 5.72, N 18.25%.

Computing details top

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA (Stoe & Cie, 2002); data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and Mercury (Macrae et al., 2006); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

	Fig. 1. The molecular structure of (I), with atom labels and 30% probability displacement ellipsoids. Only the major part of the disordered ba ligand is included. [Symmetry code: (i) -x + 1, y, -z + 1/2.]
	Fig. 2. A view of the complex showing the sheet structure parallel to the ab plane. The butyl groups, water molecules and some hydrogen bonds have been omitted for clarity. Other hydrogen bonds are shown as dashed lines. [Symmetry code: (i) -x + 1/2, y - 1/2, z.]

cis-bis[4-amino-N-(pyrimidin-2-yl)benzenesulfonamidato- κ²N,N']bis(butylamine-κN)copper(II) pentahydrate} top

Crystal data top

[Cu(C₁₀H₉N₄O₂S)₂(C₄H₁₁N)₂]·5H₂O	F(000) = 1594
M_r = 790.04	D_x = 1.347 Mg m⁻³
Orthorhombic, Pbcn	Mo Kα radiation, λ = 0.71069 Å
Hall symbol: -P 2n 2ab	Cell parameters from 30097 reflections
a = 22.623 (6) Å	θ = 1.8–27.1°
b = 10.342 (5) Å	µ = 0.74 mm⁻¹
c = 16.250 (6) Å	T = 296 K
V = 3802 (2) Å³	Prism, blue
Z = 4	0.34 × 0.21 × 0.19 mm

Data collection top

Stoe IPDS2 diffractometer	4235 independent reflections
Radiation source: fine-focus sealed tube	2098 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.085
rotation method scans	θ_max = 27.2°, θ_min = 1.8°
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	h = −28→28
T_min = 0.821, T_max = 0.900	k = −13→13
57960 measured reflections	l = −20→20

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.141	H-atom parameters constrained
S = 0.90	w = 1/[σ²(F_o²) + (0.0787P)²] where P = (F_o² + 2F_c²)/3
4235 reflections	(Δ/σ)_max < 0.001
234 parameters	Δρ_max = 0.65 e Å⁻³
0 restraints	Δρ_min = −0.45 e Å⁻³

Crystal data top

[Cu(C₁₀H₉N₄O₂S)₂(C₄H₁₁N)₂]·5H₂O	V = 3802 (2) Å³
M_r = 790.04	Z = 4
Orthorhombic, Pbcn	Mo Kα radiation
a = 22.623 (6) Å	µ = 0.74 mm⁻¹
b = 10.342 (5) Å	T = 296 K
c = 16.250 (6) Å	0.34 × 0.21 × 0.19 mm

Data collection top

Stoe IPDS2 diffractometer	4235 independent reflections
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	2098 reflections with I > 2σ(I)
T_min = 0.821, T_max = 0.900	R_int = 0.085
57960 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	0 restraints
wR(F²) = 0.141	H-atom parameters constrained
S = 0.90	Δρ_max = 0.65 e Å⁻³
4235 reflections	Δρ_min = −0.45 e Å⁻³
234 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)
C1	0.33524 (14)	0.7316 (3)	0.45323 (19)	0.0565 (8)
C2	0.29637 (16)	0.8185 (4)	0.4879 (2)	0.0684 (9)
H2	0.3109	0.8929	0.5129	0.082*
C3	0.23634 (16)	0.7970 (4)	0.4860 (2)	0.0752 (10)
H3	0.2108	0.8559	0.5107	0.090*
C4	0.21358 (15)	0.6879 (4)	0.4473 (2)	0.0689 (9)
C5	0.25293 (17)	0.6011 (4)	0.4128 (2)	0.0728 (10)
H5	0.2387	0.5271	0.3870	0.087*
C6	0.31255 (15)	0.6227 (3)	0.4160 (2)	0.0664 (9)
H6	0.3382	0.5628	0.3927	0.080*
C7	0.41743 (13)	0.8242 (3)	0.3032 (2)	0.0565 (8)
C8	0.36943 (17)	0.9966 (4)	0.2474 (3)	0.0800 (11)
H8	0.3452	1.0686	0.2536	0.096*
C9	0.39032 (17)	0.9691 (4)	0.1702 (3)	0.0847 (12)
H9	0.3802	1.0190	0.1247	0.102*
C10	0.42700 (16)	0.8638 (4)	0.1637 (2)	0.0745 (10)
H10	0.4427	0.8426	0.1125	0.089*
C11	0.3906 (2)	0.4981 (5)	0.2216 (4)	0.124 (2)
H11A	0.3706	0.5801	0.2136	0.149*
H11B	0.3925	0.4841	0.2806	0.149*
C12	0.3518 (2)	0.4000 (5)	0.1892 (4)	0.1116 (17)
H12A	0.3740	0.3199	0.1854	0.134*
H12B	0.3409	0.4246	0.1337	0.134*
C13A	0.2962 (4)	0.3733 (8)	0.2362 (5)	0.088 (2)	0.605 (8)
H13A	0.2764	0.4549	0.2461	0.105*	0.605 (8)
H13B	0.3070	0.3376	0.2893	0.105*	0.605 (8)
C13B	0.2848 (5)	0.4111 (13)	0.1823 (9)	0.088 (2)	0.395 (8)
H13C	0.2709	0.4851	0.2134	0.105*	0.395 (8)
H13D	0.2733	0.4223	0.1253	0.105*	0.395 (8)
C14A	0.2505 (12)	0.277 (3)	0.1934 (18)	0.108 (4)	0.605 (8)
H14A	0.2169	0.2658	0.2286	0.162*	0.605 (8)
H14B	0.2692	0.1954	0.1841	0.162*	0.605 (8)
H14C	0.2380	0.3132	0.1418	0.162*	0.605 (8)
C14B	0.261 (2)	0.299 (4)	0.213 (3)	0.108 (4)	0.395 (8)
H14D	0.2186	0.3043	0.2115	0.162*	0.395 (8)
H14E	0.2736	0.2879	0.2693	0.162*	0.395 (8)
H14F	0.2741	0.2270	0.1810	0.162*	0.395 (8)
N1	0.43499 (11)	0.7422 (3)	0.36300 (16)	0.0586 (7)
N2	0.38163 (12)	0.9265 (3)	0.31428 (17)	0.0635 (7)
N3	0.44067 (12)	0.7910 (3)	0.22883 (16)	0.0596 (7)
N4	0.44912 (14)	0.5158 (3)	0.1947 (2)	0.0896 (10)
H4A	0.4478	0.5356	0.1408	0.108*
H4B	0.4677	0.4391	0.1990	0.108*
N5	0.15418 (15)	0.6661 (4)	0.4447 (2)	0.1001 (11)
H5A	0.1407	0.5976	0.4213	0.120*
H5B	0.1302	0.7209	0.4664	0.120*
O1	0.42208 (10)	0.8844 (2)	0.48919 (14)	0.0690 (6)
O2	0.43907 (10)	0.6530 (2)	0.49927 (15)	0.0731 (7)
O3	0.02149 (14)	0.6126 (3)	0.4017 (2)	0.1193 (11)
O4	0.0000	0.7493 (5)	0.2500	0.151 (2)
O5	0.43200 (14)	0.3833 (3)	0.5011 (3)	0.1410 (15)
S2	0.41156 (4)	0.75774 (8)	0.45398 (5)	0.0588 (2)
Cu1	0.5000	0.64823 (6)	0.2500	0.0647 (2)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0482 (17)	0.062 (2)	0.0590 (17)	−0.0025 (16)	0.0034 (15)	0.0033 (16)
C2	0.056 (2)	0.068 (2)	0.081 (2)	−0.0050 (18)	0.0009 (18)	−0.0092 (19)
C3	0.053 (2)	0.080 (2)	0.093 (3)	0.0044 (19)	0.0133 (19)	−0.005 (2)
C4	0.051 (2)	0.078 (2)	0.078 (2)	−0.0120 (19)	−0.0005 (17)	0.007 (2)
C5	0.059 (2)	0.077 (2)	0.083 (2)	−0.013 (2)	−0.0008 (19)	−0.005 (2)
C6	0.054 (2)	0.069 (2)	0.076 (2)	−0.0018 (17)	0.0045 (17)	−0.0079 (18)
C7	0.0426 (17)	0.064 (2)	0.063 (2)	−0.0072 (16)	0.0046 (15)	0.0020 (16)
C8	0.067 (2)	0.084 (3)	0.088 (3)	0.012 (2)	−0.003 (2)	0.020 (2)
C9	0.068 (2)	0.105 (3)	0.081 (3)	0.004 (2)	−0.003 (2)	0.028 (2)
C10	0.057 (2)	0.100 (3)	0.066 (2)	−0.001 (2)	0.0069 (17)	0.007 (2)
C11	0.089 (3)	0.096 (3)	0.187 (6)	−0.029 (3)	0.050 (3)	−0.047 (4)
C12	0.080 (3)	0.108 (4)	0.146 (4)	−0.006 (3)	0.002 (3)	−0.049 (3)
C13A	0.079 (4)	0.092 (5)	0.092 (5)	−0.012 (4)	0.002 (4)	−0.018 (4)
C13B	0.079 (4)	0.092 (5)	0.092 (5)	−0.012 (4)	0.002 (4)	−0.018 (4)
C14A	0.081 (11)	0.103 (9)	0.140 (15)	−0.017 (6)	−0.014 (8)	−0.034 (8)
C14B	0.081 (11)	0.103 (9)	0.140 (15)	−0.017 (6)	−0.014 (8)	−0.034 (8)
N1	0.0480 (15)	0.0615 (16)	0.0664 (16)	0.0056 (13)	0.0059 (12)	0.0030 (14)
N2	0.0588 (17)	0.0636 (17)	0.0679 (17)	0.0086 (14)	0.0022 (14)	0.0019 (15)
N3	0.0506 (16)	0.0697 (17)	0.0585 (16)	−0.0061 (14)	0.0041 (12)	−0.0026 (14)
N4	0.070 (2)	0.087 (2)	0.112 (3)	0.0022 (18)	0.0034 (19)	−0.021 (2)
N5	0.0505 (18)	0.110 (3)	0.140 (3)	−0.0131 (19)	0.004 (2)	−0.009 (2)
O1	0.0574 (14)	0.0741 (15)	0.0755 (14)	−0.0064 (12)	−0.0044 (12)	−0.0138 (12)
O2	0.0606 (15)	0.0799 (16)	0.0787 (15)	0.0053 (13)	−0.0093 (12)	0.0243 (13)
O3	0.079 (2)	0.125 (3)	0.155 (3)	0.0017 (19)	0.018 (2)	−0.008 (2)
O4	0.174 (6)	0.091 (3)	0.188 (6)	0.000	0.053 (4)	0.000
O5	0.073 (2)	0.096 (2)	0.253 (5)	0.0007 (18)	−0.015 (3)	−0.001 (3)
S2	0.0469 (4)	0.0667 (5)	0.0629 (5)	−0.0008 (4)	−0.0020 (4)	0.0035 (4)
Cu1	0.0516 (3)	0.0697 (4)	0.0726 (4)	0.000	0.0051 (3)	0.000

Geometric parameters (Å, º) top

C1—C6	1.377 (5)	C12—C13B	1.524 (13)
C1—C2	1.378 (5)	C12—H12A	0.970
C1—S2	1.748 (3)	C12—H12B	0.970
C2—C3	1.377 (5)	C13A—C14A	1.592 (16)
C2—H2	0.930	C13A—H13A	0.970
C3—C4	1.391 (5)	C13A—H13B	0.970
C3—H3	0.930	C13B—C14B	1.37 (5)
C4—N5	1.363 (5)	C13B—H13C	0.970
C4—C5	1.382 (5)	C13B—H13D	0.970
C5—C6	1.368 (5)	C14A—H14A	0.960
C5—H5	0.930	C14A—H14B	0.960
C6—H6	0.930	C14A—H14C	0.960
C7—N2	1.344 (4)	C14B—H14D	0.960
C7—N1	1.351 (4)	C14B—H14E	0.960
C7—N3	1.361 (4)	C14B—H14F	0.960
C8—N2	1.334 (5)	N1—S2	1.579 (3)
C8—C9	1.371 (6)	N3—Cu1	2.025 (3)
C8—H8	0.930	N4—Cu1	2.002 (3)
C9—C10	1.373 (5)	N4—H4A	0.900
C9—H9	0.930	N4—H4B	0.900
C10—N3	1.336 (4)	N5—H5A	0.860
C10—H10	0.930	N5—H5B	0.860
C11—N4	1.407 (5)	O1—S2	1.449 (2)
C11—C12	1.441 (6)	O2—S2	1.450 (2)
C11—H11A	0.970	Cu1—N4ⁱ	2.002 (3)
C11—H11B	0.970	Cu1—N3ⁱ	2.025 (3)
C12—C13A	1.496 (9)

C6—C1—C2	118.4 (3)	C12—C13A—H13B	108.3
C6—C1—S2	119.9 (3)	C14A—C13A—H13B	108.3
C2—C1—S2	121.8 (3)	H13A—C13A—H13B	107.4
C3—C2—C1	121.0 (3)	C14B—C13B—C12	107 (2)
C3—C2—H2	119.5	C14B—C13B—H13C	110.2
C1—C2—H2	119.5	C12—C13B—H13C	110.2
C2—C3—C4	120.4 (4)	C14B—C13B—H13D	110.2
C2—C3—H3	119.8	C12—C13B—H13D	110.2
C4—C3—H3	119.8	H13C—C13B—H13D	108.5
N5—C4—C5	121.0 (4)	C13A—C14A—H14A	109.5
N5—C4—C3	120.8 (4)	C13A—C14A—H14B	109.5
C5—C4—C3	118.1 (3)	H14A—C14A—H14B	109.5
C6—C5—C4	120.9 (4)	C13A—C14A—H14C	109.5
C6—C5—H5	119.6	H14A—C14A—H14C	109.5
C4—C5—H5	119.6	H14B—C14A—H14C	109.5
C5—C6—C1	121.2 (3)	C13B—C14B—H14D	109.5
C5—C6—H6	119.4	C13B—C14B—H14E	109.5
C1—C6—H6	119.4	H14D—C14B—H14E	109.5
N2—C7—N1	125.1 (3)	C13B—C14B—H14F	109.5
N2—C7—N3	123.4 (3)	H14D—C14B—H14F	109.5
N1—C7—N3	111.5 (3)	H14E—C14B—H14F	109.5
N2—C8—C9	124.2 (4)	C7—N1—S2	120.8 (2)
N2—C8—H8	117.9	C8—N2—C7	116.2 (3)
C9—C8—H8	117.9	C10—N3—C7	118.1 (3)
C8—C9—C10	116.3 (4)	C10—N3—Cu1	134.4 (2)
C8—C9—H9	121.8	C7—N3—Cu1	106.8 (2)
C10—C9—H9	121.8	C11—N4—Cu1	119.4 (3)
N3—C10—C9	121.7 (4)	C11—N4—H4A	107.5
N3—C10—H10	119.1	Cu1—N4—H4A	107.5
C9—C10—H10	119.1	C11—N4—H4B	107.5
N4—C11—C12	123.4 (4)	Cu1—N4—H4B	107.5
N4—C11—H11A	106.5	H4A—N4—H4B	107.0
C12—C11—H11A	106.5	C4—N5—H5A	120.0
N4—C11—H11B	106.5	C4—N5—H5B	120.0
C12—C11—H11B	106.5	H5A—N5—H5B	120.0
H11A—C11—H11B	106.5	O1—S2—O2	113.88 (15)
C11—C12—C13A	117.0 (5)	O1—S2—N1	113.99 (15)
C11—C12—C13B	125.3 (6)	O2—S2—N1	104.77 (15)
C11—C12—H12A	108.0	O1—S2—C1	107.76 (15)
C13A—C12—H12A	108.0	O2—S2—C1	108.16 (15)
C13B—C12—H12A	125.1	N1—S2—C1	108.02 (15)
C11—C12—H12B	108.0	N4—Cu1—N4ⁱ	93.7 (2)
C13A—C12—H12B	108.0	N4—Cu1—N3ⁱ	162.98 (13)
C13B—C12—H12B	70.1	N4ⁱ—Cu1—N3ⁱ	92.38 (13)
H12A—C12—H12B	107.3	N4—Cu1—N3	92.38 (13)
C12—C13A—C14A	116.0 (14)	N4ⁱ—Cu1—N3	162.98 (13)
C12—C13A—H13A	108.3	N3ⁱ—Cu1—N3	86.36 (16)
C14A—C13A—H13A	108.3

C6—C1—C2—C3	0.5 (5)	C9—C10—N3—Cu1	−169.6 (3)
S2—C1—C2—C3	179.3 (3)	N2—C7—N3—C10	−0.2 (5)
C1—C2—C3—C4	−1.4 (6)	N1—C7—N3—C10	179.9 (3)
C2—C3—C4—N5	−179.6 (4)	N2—C7—N3—Cu1	171.8 (2)
C2—C3—C4—C5	1.4 (6)	N1—C7—N3—Cu1	−8.1 (3)
N5—C4—C5—C6	−179.5 (4)	C12—C11—N4—Cu1	−176.0 (5)
C3—C4—C5—C6	−0.5 (6)	C7—N1—S2—O1	−55.6 (3)
C4—C5—C6—C1	−0.4 (6)	C7—N1—S2—O2	179.3 (2)
C2—C1—C6—C5	0.4 (5)	C7—N1—S2—C1	64.1 (3)
S2—C1—C6—C5	−178.4 (3)	C6—C1—S2—O1	174.2 (3)
N2—C8—C9—C10	−1.4 (6)	C2—C1—S2—O1	−4.6 (3)
C8—C9—C10—N3	1.1 (6)	C6—C1—S2—O2	−62.3 (3)
N4—C11—C12—C13A	166.6 (7)	C2—C1—S2—O2	118.9 (3)
N4—C11—C12—C13B	−149.2 (9)	C6—C1—S2—N1	50.6 (3)
C11—C12—C13A—C14A	172.7 (14)	C2—C1—S2—N1	−128.2 (3)
C13B—C12—C13A—C14A	59.0 (16)	C11—N4—Cu1—N4ⁱ	108.9 (5)
C11—C12—C13B—C14B	−132 (2)	C11—N4—Cu1—N3ⁱ	−140.5 (5)
C13A—C12—C13B—C14B	−42 (2)	C11—N4—Cu1—N3	−55.2 (4)
N2—C7—N1—S2	2.7 (4)	C10—N3—Cu1—N4	−79.3 (4)
N3—C7—N1—S2	−177.4 (2)	C7—N3—Cu1—N4	110.6 (2)
C9—C8—N2—C7	0.9 (6)	C10—N3—Cu1—N4ⁱ	169.9 (4)
N1—C7—N2—C8	179.8 (3)	C7—N3—Cu1—N4ⁱ	−0.1 (5)
N3—C7—N2—C8	−0.1 (5)	C10—N3—Cu1—N3ⁱ	83.7 (3)
C9—C10—N3—C7	−0.4 (5)	C7—N3—Cu1—N3ⁱ	−86.4 (2)

Symmetry code: (i) −x+1, y, −z+1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N5—H5A···N2ⁱⁱ	0.86	2.53	3.359 (5)	162
N4—H4A···O5ⁱⁱⁱ	0.90	2.45	3.337 (6)	171
N4—H4B···O4^iv	0.90	2.25	3.119 (6)	161
N5—H5B···O5^v	0.86	2.26	3.113 (5)	170

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

Experimental details

Crystal data
Chemical formula	[Cu(C₁₀H₉N₄O₂S)₂(C₄H₁₁N)₂]·5H₂O
M_r	790.04
Crystal system, space group	Orthorhombic, Pbcn
Temperature (K)	296
a, b, c (Å)	22.623 (6), 10.342 (5), 16.250 (6)
V (Å³)	3802 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.74
Crystal size (mm)	0.34 × 0.21 × 0.19

Data collection
Diffractometer	Stoe IPDS2 diffractometer
Absorption correction	Integration (X-RED32; Stoe & Cie, 2002)
T_min, T_max	0.821, 0.900
No. of measured, independent and observed [I > 2σ(I)] reflections	57960, 4235, 2098
R_int	0.085
(sin θ/λ)_max (Å⁻¹)	0.644

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.141, 0.90
No. of reflections	4235
No. of parameters	234
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.65, −0.45

Computer programs: X-AREA (Stoe & Cie, 2002), X-RED32 (Stoe & Cie, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997) and Mercury (Macrae et al., 2006), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N5—H5A···N2ⁱ	0.86	2.53	3.359 (5)	161.7
N4—H4A···O5ⁱⁱ	0.90	2.45	3.337 (6)	170.5
N4—H4B···O4ⁱⁱⁱ	0.90	2.25	3.119 (6)	161.4
N5—H5B···O5^iv	0.86	2.26	3.113 (5)	169.6

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

Acknowledgements

The authors thank the Faculty of Arts and Sciences, Ondokuz Mayıs University, Turkey, for the use of the Stoe IPDS2 diffractometer (purchased under grant No. F279 of the University Research Fund).

References

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