Bis(4-amino-benzene-sulfonamide-κN (4))di-chlorido-zinc.

In the title compound, [ZnCl2(C6H8N2O2S)2], the Zn(II) ion lies on a twofold rotation axis and has a slightly distorted tetra-hedral coordination geometry, involving two Cl atoms and two N atoms from the amino groups attached directly to the benzene rings [Zn-Cl = 2.2288 (16) Å and Zn-N = 2.060 (5) Å]. The dihedral angle between the benzene rings is 67.1 (3)°. The crystal packing can be describe as layers in a zigzag arrangement parallel to (001). The amine H atoms act as donor atoms and participate in inter-molecular N-H⋯O and N-H⋯Cl hydrogen bonds, forming a three-dimensional network.

Related literature

For background to sulfanilamides and their applications, see: Wong & Giandomenico (1999 ▶); Ferrer et al. (1990 ▶); Supuran et al. (1998 ▶); Medina et al. (1999 ▶). For related structures, see: Benmebarek et al. (2012 ▶, 2013 ▶).

Experimental

Crystal data

[ZnCl2(C6H8N2O2S)2]

M = 480.68

Orthorhombic,

a = 7.7957 (15) Å

b = 27.916 (6) Å

c = 8.2701 (17) Å

V = 1799.8 (6) Å3

Z = 4

Mo Kα radiation

μ = 1.92 mm−1

T = 150 K

0.23 × 0.19 × 0.15 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2002 ▶) T min = 0.639, T max = 0.746

6151 measured reflections

2051 independent reflections

1563 reflections with I > 2σ(I)

R int = 0.075

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.067

S = 1.00

2051 reflections

120 parameters

3 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.38 e Å−3

Δρmin = −0.40 e Å−3

Absolute structure: Flack parameter determined using 601 quotients [(I +)−(I −)]/[(I +)+(I −)] (Parsons et al., 2013 ▶)

Absolute structure parameter: 0.037 (18)

Data collection: APEX2 (Bruker, 2011 ▶); cell refinement: SAINT (Bruker, 2011 ▶); data reduction: SAINT; program(s) used to solve structure: SIR2002 (Burla et al., 2005 ▶); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶) and DIAMOND (Brandenburg & Berndt, 2001 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶).

Crystal structure: contains datablock(s) I. DOI: 10.1107/S160053681303417X/lh5676sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681303417X/lh5676Isup2.hkl

Additional supporting information: crystallographic information; 3D view; checkCIF report

[ZnCl2(C6H8N2O2S)2]	Dx = 1.774 Mg m−3
Mr = 480.68	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Aba2	Cell parameters from 805 reflections
a = 7.7957 (15) Å	θ = 2.9–22.3°
b = 27.916 (6) Å	µ = 1.92 mm−1
c = 8.2701 (17) Å	T = 150 K
V = 1799.8 (6) Å3	Block, colourless
Z = 4	0.23 × 0.19 × 0.15 mm
F(000) = 976

Bruker APEXII CCD diffractometer	1563 reflections with I > 2σ(I)
Radiation source: sealed tube	Rint = 0.075
φ and ω scans	θmax = 27.4°, θmin = 2.9°
Absorption correction: multi-scan (SADABS; Bruker, 2002)	h = −10→10
Tmin = 0.639, Tmax = 0.746	k = −36→35
6151 measured reflections	l = −10→10
2051 independent reflections

Refinement on F2	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.040	w = 1/[σ2(Fo2)] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.067	(Δ/σ)max < 0.001
S = 1.00	Δρmax = 0.38 e Å−3
2051 reflections	Δρmin = −0.40 e Å−3
120 parameters	Absolute structure: Flack parameter determined using 601 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
3 restraints	Absolute structure parameter: 0.037 (18)

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

	x	y	z	Uiso*/Ueq
C1	0.1797 (7)	0.0904 (2)	−0.0925 (8)	0.0181 (15)
C2	0.1224 (6)	0.1288 (2)	−0.0041 (9)	0.0202 (13)
H2	0.0028	0.1339	0.0093	0.024*
C3	0.2387 (8)	0.1598 (2)	0.0653 (8)	0.0205 (15)
H3	0.2002	0.1866	0.1263	0.025*
C4	0.4132 (7)	0.1514 (2)	0.0446 (8)	0.0182 (14)
C5	0.4705 (7)	0.1121 (2)	−0.0415 (9)	0.0214 (16)
H5	0.5901	0.1065	−0.0532	0.026*
C6	0.3546 (7)	0.0811 (2)	−0.1103 (7)	0.0188 (15)
H6	0.3928	0.0539	−0.1689	0.023*
N1	0.0594 (5)	0.05705 (19)	−0.1656 (7)	0.0221 (13)
H1A	0.1090	0.0447	−0.2676	0.026*
H1B	−0.0475	0.0744	−0.1929	0.026*
N2	0.6629 (6)	0.21766 (18)	−0.0154 (9)	0.0267 (12)
H1N	0.591 (6)	0.235 (2)	−0.069 (7)	0.032*
H2N	0.712 (7)	0.1973 (18)	−0.079 (7)	0.032*
O1	0.6944 (5)	0.15998 (16)	0.2073 (6)	0.0275 (12)
O2	0.4808 (6)	0.22535 (16)	0.2260 (6)	0.0312 (12)
S1	0.56714 (18)	0.18997 (6)	0.1307 (2)	0.0204 (3)
Cl1	−0.22591 (17)	0.02497 (6)	0.1242 (2)	0.0273 (4)
Zn1	0.0000	0.0000	−0.01787 (14)	0.0176 (2)

	U11	U22	U33	U12	U13	U23
C1	0.023 (3)	0.019 (4)	0.012 (3)	−0.003 (3)	−0.004 (3)	0.007 (3)
C2	0.020 (3)	0.024 (3)	0.017 (4)	0.004 (2)	0.002 (3)	0.005 (4)
C3	0.027 (3)	0.020 (4)	0.015 (3)	0.001 (3)	−0.001 (3)	0.002 (3)
C4	0.025 (3)	0.016 (3)	0.014 (3)	0.001 (3)	−0.002 (3)	0.001 (3)
C5	0.021 (3)	0.024 (3)	0.019 (4)	0.002 (3)	0.005 (3)	0.004 (3)
C6	0.022 (3)	0.018 (4)	0.017 (4)	0.004 (3)	0.005 (3)	−0.002 (3)
N1	0.018 (2)	0.031 (3)	0.017 (3)	−0.004 (2)	−0.001 (2)	0.001 (3)
N2	0.039 (3)	0.023 (3)	0.019 (3)	−0.007 (2)	−0.002 (4)	0.003 (4)
O1	0.030 (3)	0.025 (3)	0.027 (3)	0.003 (2)	−0.011 (2)	0.000 (2)
O2	0.041 (3)	0.027 (3)	0.026 (3)	0.007 (2)	−0.006 (2)	−0.012 (2)
S1	0.0261 (7)	0.0209 (9)	0.0144 (8)	0.0013 (6)	−0.0036 (8)	−0.0010 (9)
Cl1	0.0259 (7)	0.0307 (9)	0.0252 (9)	0.0073 (7)	0.0086 (9)	0.0030 (10)
Zn1	0.0164 (4)	0.0218 (5)	0.0145 (5)	−0.0010 (5)	0.000	0.000

C1—C2	1.371 (8)	N1—Zn1	2.060 (5)
C1—C6	1.396 (7)	N1—H1A	0.9900
C1—N1	1.454 (7)	N1—H1B	0.9900
C2—C3	1.380 (8)	N2—S1	1.617 (6)
C2—H2	0.9500	N2—H1N	0.86 (3)
C3—C4	1.391 (8)	N2—H2N	0.86 (3)
C3—H3	0.9500	O1—S1	1.444 (4)
C4—C5	1.382 (8)	O2—S1	1.432 (5)
C4—S1	1.763 (6)	Cl1—Zn1	2.2288 (16)
C5—C6	1.374 (8)	Zn1—N1i	2.060 (5)
C5—H5	0.9500	Zn1—Cl1i	2.2288 (16)
C6—H6	0.9500
C2—C1—C6	121.3 (6)	Zn1—N1—H1A	108.9
C2—C1—N1	120.8 (5)	C1—N1—H1B	108.9
C6—C1—N1	117.9 (6)	Zn1—N1—H1B	108.9
C1—C2—C3	119.9 (5)	H1A—N1—H1B	107.8
C1—C2—H2	120.1	S1—N2—H1N	110 (4)
C3—C2—H2	120.1	S1—N2—H2N	110 (4)
C2—C3—C4	119.0 (6)	H1N—N2—H2N	110 (7)
C2—C3—H3	120.5	O2—S1—O1	118.8 (3)
C4—C3—H3	120.5	O2—S1—N2	107.4 (3)
C5—C4—C3	120.9 (6)	O1—S1—N2	106.7 (3)
C5—C4—S1	118.2 (4)	O2—S1—C4	108.9 (3)
C3—C4—S1	120.8 (5)	O1—S1—C4	106.9 (3)
C6—C5—C4	120.0 (5)	N2—S1—C4	107.7 (3)
C6—C5—H5	120.0	N1i—Zn1—N1	107.2 (3)
C4—C5—H5	120.0	N1i—Zn1—Cl1i	104.38 (14)
C5—C6—C1	118.8 (6)	N1—Zn1—Cl1i	112.14 (13)
C5—C6—H6	120.6	N1i—Zn1—Cl1	112.14 (13)
C1—C6—H6	120.6	N1—Zn1—Cl1	104.38 (14)
C1—N1—Zn1	113.2 (4)	Cl1i—Zn1—Cl1	116.38 (11)
C1—N1—H1A	108.9
C6—C1—C2—C3	1.9 (10)	N1—C1—C6—C5	−179.7 (6)
N1—C1—C2—C3	179.5 (6)	C2—C1—N1—Zn1	−91.0 (6)
C1—C2—C3—C4	−0.3 (10)	C6—C1—N1—Zn1	86.8 (6)
C2—C3—C4—C5	−1.2 (10)	C5—C4—S1—O2	−174.7 (5)
C2—C3—C4—S1	−180.0 (5)	C3—C4—S1—O2	4.1 (6)
C3—C4—C5—C6	1.1 (10)	C5—C4—S1—O1	−45.2 (6)
S1—C4—C5—C6	179.9 (5)	C3—C4—S1—O1	133.6 (5)
C4—C5—C6—C1	0.5 (10)	C5—C4—S1—N2	69.1 (6)
C2—C1—C6—C5	−2.0 (10)	C3—C4—S1—N2	−112.0 (5)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···Cl1ii	0.99	2.50	3.327 (5)	141
N2—H1N···O2iii	0.86 (5)	2.10 (6)	2.891 (8)	152 (5)
N2—H2N···O1iv	0.86 (5)	2.18 (6)	3.015 (8)	163 (5)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯Cl1i	0.99	2.50	3.327 (5)	141
N2—H1N⋯O2ii	0.86 (5)	2.10 (6)	2.891 (8)	152 (5)
N2—H2N⋯O1iii	0.86 (5)	2.18 (6)	3.015 (8)	163 (5)

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