cis-Bis(butyl-amine-κN)bis-[sulfa-diazine(1-)-κN,N']copper(II) penta-hydrate.

In the title compound {systematic name: cis-bis-[4-amino-N-(pyrimidin-2-yl)benzene-sulfonamidato-κ(2)N,N']bis-(butyl-amine-κN)copper(II) penta-hydrate}, [Cu(C(10)H(9)N(4)O(2)S)(2)(C(4)H(11)N)(2)]·5H(2)O or [Cu(sdz)(2)(ba)(2)]·5H(2)O [ba is butyl-amine and sdz = sulfadiazine(1-)], the copper(II) cation is six-coordinated by four N atoms of two sulfadiazine ligands and two N atoms of butyl-amine ligands. The copper(II) ion and one of the water mol-ecules 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 tetra-hedral. The crystal structure involves inter-molecular 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 = 790.04

Orthorhombic,

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[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.141

S = 0.90

4235 reflections

234 parameters

H-atom parameters constrained

Δρmax = 0.65 e Å−3

Δρmin = −0.45 e Å−3

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 ▶).

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

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

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[Cu(C10H9N4O2S)2(C4H11N)2]·5H2O	F000 = 1594
Mr = 790.04	Dx = 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 = 1.8–27.1º
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

Stoe IPDS2 diffractometer	4235 independent reflections
Radiation source: fine-focus sealed tube	2098 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.085
T = 296 K	θmax = 27.2º
rotation method scans	θmin = 1.8º
Absorption correction: integration(X-RED32; Stoe & Cie, 2002)	h = −28→28
Tmin = 0.821, Tmax = 0.900	k = −13→13
57960 measured reflections	l = −20→20

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)] = 0.048	H-atom parameters constrained
wR(F2) = 0.141	w = 1/[σ2(Fo2) + (0.0787P)2] where P = (Fo2 + 2Fc2)/3
S = 0.90	(Δ/σ)max < 0.001
4235 reflections	Δρmax = 0.65 e Å−3
234 parameters	Δρmin = −0.45 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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.

	x	y	z	Uiso*/Ueq	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)

	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

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)

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···O4iv	0.90	2.25	3.119 (6)	161
N5—H5B···O5v	0.86	2.26	3.113 (5)	170

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⋯O5iv	0.86	2.26	3.113 (5)	170

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .