Bis(S-benzyl­isothio­uronium) tetra­chloridozincate(II)

Gayathri, D.; Velmurugan, D.; Hemalatha, P.; Veeravazhuthi, V.; Ravikumar, K.

doi:10.1107/S1600536808015195

metal-organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 64| Part 6| June 2008| Pages m848-m849

doi:10.1107/S1600536808015195

Open

access

Bis(S-benzylisothiouronium) tetrachloridozincate(II)

D. Gayathri,^a D. Velmurugan,^a ^* P. Hemalatha,^b V. Veeravazhuthi ^c and K. Ravikumar ^d

^aCentre of Advanced Study in Crystallography and Biophysics, University of Madras, Guindy Campus, Chennai 600 025, India, ^bDepartment of Physics, PSG College of Technology, Coimbatore 641 004, India, ^cDepartment of Physics, PSG College of Arts and Science, Coimbatore 641 101, India, and ^dLaboratory of X-ray Crystallography, Indian Institute of Chemical Technology, Hyderabad 500 007, India
^*Correspondence e-mail: d_velu@yahoo.com

(Received 5 May 2008; accepted 20 May 2008; online 30 May 2008)

The asymmetric unit of the title compound, (C₈H₁₁N₂S)₂[ZnCl₄], contains two S-benzylisothiouronium cations which differ in the C—C—S—C torsion angle [165.3 (2) and 81.9 (2)°] and a tetrahedral tetrachloridozincate anion. The crystal structure is stabilized by N—H⋯Cl, C—H⋯Cl and C—H⋯S interactions.

Related literature

For related literature, see: Hemalatha et al. (2006 ); Zhang et al. (1994 ); Barker & Powell (1998 ).

Experimental

Crystal data

(C₈H₁₁N₂S)₂[ZnCl₄]
M_r = 541.67
Monoclinic, P 2₁ /c
a = 15.2135 (11) Å
b = 6.4475 (5) Å
c = 23.9277 (18) Å
β = 95.368 (1)°
V = 2336.8 (3) Å³
Z = 4
Mo Kα radiation
μ = 1.70 mm⁻¹
T = 293 (2) K
0.27 × 0.23 × 0.21 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: none
25129 measured reflections
5481 independent reflections
4986 reflections with I > 2σ(I)
R_int = 0.026

Refinement

R[F² > 2σ(F²)] = 0.029
wR(F²) = 0.073
S = 1.08
5481 reflections
244 parameters
H-atom parameters constrained
Δρ_max = 0.41 e Å⁻³
Δρ_min = −0.32 e Å⁻³

Table 1
Selected bond lengths (Å)

Cl1—Zn1	2.2792 (5)
Cl2—Zn1	2.2650 (5)
Cl3—Zn1	2.2718 (5)
Cl4—Zn1	2.2589 (5)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯Cl3	0.86	2.68	3.372 (2)	139
N1—H1B⋯Cl2ⁱ	0.86	2.45	3.255 (2)	157
N2—H2A⋯Cl4	0.86	2.53	3.219 (2)	138
N2—H2B⋯Cl3ⁱⁱ	0.86	2.62	3.262 (2)	132
N3—H3A⋯Cl1ⁱⁱⁱ	0.86	2.72	3.469 (2)	147
N3—H3A⋯Cl4ⁱⁱⁱ	0.86	2.65	3.244 (2)	128
N3—H3B⋯Cl1^iv	0.86	2.44	3.283 (2)	166
N4—H4A⋯Cl1ⁱⁱⁱ	0.86	2.49	3.290 (2)	156
N4—H4B⋯Cl2ⁱ	0.86	2.62	3.447 (2)	163
C15—H15A⋯S1	0.97	2.87	3.591 (2)	132
C15—H15A⋯Cl2^v	0.97	2.77	3.556 (2)	139
C15—H15B⋯Cl2ⁱ	0.97	2.65	3.594 (2)	164
Symmetry codes: (i) -x+1, -y, -z+1; (ii) x, y+1, z; (iii) x-1, y, z; (iv) x-1, y+1, z; (v) -x+1, -y+1, -z+1.

Data collection: SMART (Bruker, 2001 ); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2003 ); software used to prepare material for publication: SHELXL97 and PARST (Nardelli, 1995 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808015195/bt2708sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808015195/bt2708Isup2.hkl

checkCIF report

Comment top

Most organic nonlinear optical (NLO) crystals have usually poor mechanical and thermal properties, and are susceptible to damage during processing. It is difficult to grow large optical quality crystals of these materials for device applications (Zhang et al., 1994). For further enhancement of NLO property many efforts have been made on developing new semiorganic NLO materials. The title compound is one of the new metalorganic nonlinear optical crystals. It combines the advantages of both organic and inorganic materials.

The C—N, S—C bond lengths and C—S—C and N—C—N bond angles are comparable with the similar structure reported earlier (Barker & Powell, 1998). There is a difference in the torsion angles C6—C7—S1—C8 [165.3 (2)°] and C14—C15—S2—C16 [81.9 (2)°] in the two molecules which indicates a difference in the conformation of the two molecules in the asymmetric unit.

The crystal structure (Figs. 2 and 3) is stabilized by N—H···Cl, C—H···Cl and C—H···S interactions.

Related literature top

For related literature, see: Hemalatha et al. (2006); Zhang et al.(1994); Barker & Powell (1998).

Experimental top

First S-benzylisothiouronium chloride (SBTC) was synthesized as discussed in an earlier report (Hemalatha et al., 2006). The solutions of SBTC (5 g m) and zinc chloride (1 g m) were prepared separately in minimum amount of water. Then the solutions were mixed together and stirred for 1 hr at 45°C. The resulting complex was filtered and thoroughly washed with distilled water. The product was recrystallized repeatedly from 0.2 M hydrochloric solution to grow transparent and good quality single crystals for NLO applications. Needle shape crystals were obtained from the saturated solution (with water) of the title compound by slow evaporation technique at room temperature.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PARST (Nardelli, 1995).

Figures top

	Fig. 1. The molecular structure of title compound, showing 30% probability displacement ellipsoids.
	Fig. 2. The molecular packing of the title compound showing N—H···Cl interactions viewed down c axis.
	Fig. 3. The molecular packing of the title compound showing C—H···Cl interactions viewed down c axis.

Bis(S-benzylisothiouronium) tetrachloridozincate(II) top

Crystal data top

(C₈H₁₁N₂S)₂[ZnCl₄]	F(000) = 1104
M_r = 541.67	D_x = 1.540 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2794 reflections
a = 15.2135 (11) Å	θ = 1.3–25.0°
b = 6.4475 (5) Å	µ = 1.70 mm⁻¹
c = 23.9277 (18) Å	T = 293 K
β = 95.368 (1)°	Needle, colorless
V = 2336.8 (3) Å³	0.27 × 0.23 × 0.21 mm
Z = 4

Data collection top

Bruker SMART APEX diffractometer	4986 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.026
Graphite monochromator	θ_max = 28.0°, θ_min = 1.3°
ω scans	h = −20→20
25129 measured reflections	k = −8→8
5481 independent reflections	l = −30→31

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)] = 0.029	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.073	H-atom parameters constrained
S = 1.08	w = 1/[σ²(F_o²) + (0.0325P)² + 1.0433P] where P = (F_o² + 2F_c²)/3
5481 reflections	(Δ/σ)_max = 0.001
244 parameters	Δρ_max = 0.41 e Å⁻³
0 restraints	Δρ_min = −0.32 e Å⁻³

Crystal data top

(C₈H₁₁N₂S)₂[ZnCl₄]	V = 2336.8 (3) Å³
M_r = 541.67	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 15.2135 (11) Å	µ = 1.70 mm⁻¹
b = 6.4475 (5) Å	T = 293 K
c = 23.9277 (18) Å	0.27 × 0.23 × 0.21 mm
β = 95.368 (1)°

Data collection top

Bruker SMART APEX diffractometer	4986 reflections with I > 2σ(I)
25129 measured reflections	R_int = 0.026
5481 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.029	0 restraints
wR(F²) = 0.073	H-atom parameters constrained
S = 1.08	Δρ_max = 0.41 e Å⁻³
5481 reflections	Δρ_min = −0.32 e Å⁻³
244 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
S1	0.38843 (3)	0.61059 (12)	0.36896 (3)	0.06677 (19)
N1	0.42614 (13)	0.2947 (3)	0.43326 (8)	0.0562 (5)
H1A	0.4589	0.2133	0.4547	0.067*
H1B	0.3709	0.2676	0.4258	0.067*
C1	0.36865 (17)	1.0458 (4)	0.28381 (11)	0.0598 (6)
H1	0.3774	1.1179	0.3175	0.072*
C2	0.31899 (18)	1.1338 (5)	0.23884 (15)	0.0783 (8)
H2	0.2949	1.2652	0.2423	0.094*
C3	0.3052 (2)	1.0311 (7)	0.19011 (14)	0.0869 (10)
H3	0.2718	1.0920	0.1600	0.104*
C4	0.3395 (2)	0.8398 (7)	0.18442 (11)	0.0867 (10)
H4	0.3293	0.7693	0.1505	0.104*
C5	0.39016 (18)	0.7482 (4)	0.22921 (12)	0.0663 (7)
H5	0.4137	0.6165	0.2252	0.080*
C6	0.40541 (13)	0.8523 (4)	0.27928 (9)	0.0475 (5)
C7	0.46069 (15)	0.7581 (4)	0.32779 (11)	0.0664 (7)
H7A	0.4903	0.8661	0.3506	0.080*
H7B	0.5052	0.6680	0.3143	0.080*
C8	0.46009 (12)	0.4585 (3)	0.41203 (8)	0.0399 (4)
S2	0.06186 (3)	0.66804 (7)	0.41032 (2)	0.04038 (11)
N2	0.54328 (12)	0.5038 (3)	0.42243 (9)	0.0555 (5)
H2A	0.5772	0.4246	0.4438	0.067*
H2B	0.5644	0.6130	0.4079	0.067*
C9	0.15114 (15)	0.6634 (4)	0.27656 (10)	0.0578 (6)
H9	0.1742	0.7917	0.2880	0.069*
C10	0.13285 (18)	0.6205 (6)	0.22003 (11)	0.0757 (8)
H10	0.1442	0.7203	0.1936	0.091*
C11	0.09845 (18)	0.4338 (5)	0.20262 (11)	0.0743 (8)
H11	0.0859	0.4075	0.1645	0.089*
C12	0.08244 (17)	0.2855 (5)	0.24096 (10)	0.0651 (7)
H12	0.0588	0.1583	0.2290	0.078*
C13	0.10135 (14)	0.3240 (4)	0.29755 (9)	0.0505 (5)
H13	0.0914	0.2213	0.3235	0.061*
C14	0.13496 (11)	0.5144 (3)	0.31602 (8)	0.0395 (4)
C15	0.15495 (11)	0.5601 (3)	0.37715 (8)	0.0377 (4)
H15A	0.2038	0.6572	0.3818	0.045*
H15B	0.1737	0.4330	0.3964	0.045*
C16	−0.00143 (12)	0.4549 (3)	0.42524 (8)	0.0373 (4)
N3	−0.08381 (12)	0.4941 (3)	0.43308 (8)	0.0527 (4)
H3A	−0.1180	0.3953	0.4418	0.063*
H3B	−0.1038	0.6187	0.4295	0.063*
N4	0.03000 (12)	0.2657 (3)	0.43054 (8)	0.0519 (4)
H4A	−0.0036	0.1658	0.4392	0.062*
H4B	0.0842	0.2415	0.4253	0.062*
Cl1	0.85432 (4)	−0.02098 (8)	0.44408 (3)	0.05782 (15)
Cl2	0.76342 (3)	−0.05687 (7)	0.57924 (2)	0.04173 (11)
Cl3	0.60408 (3)	−0.01885 (8)	0.44970 (3)	0.05317 (14)
Cl4	0.73327 (3)	0.42677 (7)	0.49034 (2)	0.04099 (11)
Zn1	0.738101 (13)	0.07662 (3)	0.491654 (9)	0.03552 (7)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0303 (2)	0.0860 (4)	0.0846 (4)	0.0098 (3)	0.0085 (2)	0.0446 (4)
N1	0.0452 (10)	0.0590 (11)	0.0640 (12)	−0.0027 (8)	0.0029 (8)	0.0212 (9)
C1	0.0585 (14)	0.0609 (14)	0.0607 (14)	−0.0017 (11)	0.0088 (11)	0.0033 (11)
C2	0.0582 (15)	0.0761 (18)	0.101 (2)	0.0120 (14)	0.0101 (15)	0.0311 (18)
C3	0.0568 (16)	0.128 (3)	0.073 (2)	−0.0069 (18)	−0.0079 (14)	0.039 (2)
C4	0.079 (2)	0.135 (3)	0.0459 (14)	−0.027 (2)	0.0053 (13)	−0.0046 (17)
C5	0.0617 (15)	0.0708 (16)	0.0684 (16)	−0.0033 (12)	0.0167 (12)	−0.0063 (13)
C6	0.0359 (9)	0.0567 (12)	0.0498 (11)	−0.0044 (9)	0.0043 (8)	0.0124 (10)
C7	0.0423 (12)	0.0819 (18)	0.0735 (16)	−0.0119 (11)	−0.0031 (11)	0.0342 (13)
C8	0.0349 (9)	0.0424 (10)	0.0426 (10)	0.0044 (7)	0.0041 (7)	0.0031 (8)
S2	0.0369 (2)	0.0350 (2)	0.0500 (3)	−0.00065 (18)	0.00816 (19)	−0.00128 (19)
N2	0.0386 (9)	0.0523 (10)	0.0724 (13)	−0.0025 (8)	−0.0125 (8)	0.0143 (9)
C9	0.0515 (12)	0.0654 (14)	0.0565 (13)	−0.0130 (11)	0.0048 (10)	0.0116 (11)
C10	0.0635 (15)	0.113 (2)	0.0521 (14)	−0.0118 (16)	0.0110 (12)	0.0252 (15)
C11	0.0585 (15)	0.123 (3)	0.0408 (12)	−0.0074 (16)	0.0039 (11)	−0.0090 (14)
C12	0.0599 (14)	0.0816 (17)	0.0530 (13)	−0.0095 (13)	0.0019 (11)	−0.0212 (12)
C13	0.0502 (12)	0.0544 (12)	0.0466 (11)	−0.0072 (10)	0.0025 (9)	−0.0054 (9)
C14	0.0277 (8)	0.0497 (10)	0.0409 (10)	−0.0010 (7)	0.0021 (7)	−0.0001 (8)
C15	0.0285 (8)	0.0400 (9)	0.0442 (10)	−0.0021 (7)	0.0004 (7)	−0.0029 (7)
C16	0.0372 (9)	0.0397 (9)	0.0351 (9)	−0.0016 (7)	0.0040 (7)	0.0021 (7)
N3	0.0406 (9)	0.0461 (9)	0.0741 (12)	−0.0004 (7)	0.0188 (8)	0.0060 (9)
N4	0.0483 (10)	0.0402 (9)	0.0687 (12)	0.0002 (7)	0.0130 (9)	0.0119 (8)
Cl1	0.0586 (3)	0.0431 (3)	0.0774 (4)	0.0024 (2)	0.0365 (3)	−0.0026 (2)
Cl2	0.0459 (2)	0.0367 (2)	0.0417 (2)	−0.00012 (18)	−0.00090 (18)	0.00612 (17)
Cl3	0.0417 (3)	0.0453 (3)	0.0688 (3)	−0.0069 (2)	−0.0143 (2)	0.0068 (2)
Cl4	0.0366 (2)	0.0346 (2)	0.0508 (3)	0.00228 (16)	−0.00096 (19)	0.00113 (18)
Zn1	0.03067 (11)	0.03633 (12)	0.03951 (12)	0.00107 (8)	0.00309 (8)	0.00358 (8)

Geometric parameters (Å, º) top

S1—C8	1.732 (2)	C9—C10	1.383 (4)
S1—C7	1.813 (2)	C9—C14	1.385 (3)
N1—C8	1.300 (3)	C9—H9	0.9300
N1—H1A	0.8600	C10—C11	1.362 (4)
N1—H1B	0.8600	C10—H10	0.9300
C1—C6	1.376 (3)	C11—C12	1.363 (4)
C1—C2	1.378 (4)	C11—H11	0.9300
C1—H1	0.9300	C12—C13	1.380 (3)
C2—C3	1.340 (5)	C12—H12	0.9300
C2—H2	0.9300	C13—C14	1.386 (3)
C3—C4	1.351 (5)	C13—H13	0.9300
C3—H3	0.9300	C14—C15	1.495 (3)
C4—C5	1.391 (4)	C15—H15A	0.9700
C4—H4	0.9300	C15—H15B	0.9700
C5—C6	1.374 (3)	C16—N3	1.309 (2)
C5—H5	0.9300	C16—N4	1.312 (2)
C6—C7	1.497 (3)	N3—H3A	0.8600
C7—H7A	0.9700	N3—H3B	0.8600
C7—H7B	0.9700	N4—H4A	0.8600
C8—N2	1.300 (3)	N4—H4B	0.8600
S2—C16	1.734 (2)	Cl1—Zn1	2.2792 (5)
S2—C15	1.825 (2)	Cl2—Zn1	2.2650 (5)
N2—H2A	0.8600	Cl3—Zn1	2.2718 (5)
N2—H2B	0.8600	Cl4—Zn1	2.2589 (5)

C8—S1—C7	103.9 (1)	C14—C9—H9	120.1
C8—N1—H1A	120.0	C11—C10—C9	120.8 (3)
C8—N1—H1B	120.0	C11—C10—H10	119.6
H1A—N1—H1B	120.0	C9—C10—H10	119.6
C6—C1—C2	120.6 (3)	C10—C11—C12	120.1 (2)
C6—C1—H1	119.7	C10—C11—H11	119.9
C2—C1—H1	119.7	C12—C11—H11	119.9
C3—C2—C1	120.4 (3)	C11—C12—C13	120.0 (2)
C3—C2—H2	119.8	C11—C12—H12	120.0
C1—C2—H2	119.8	C13—C12—H12	120.0
C2—C3—C4	120.6 (3)	C12—C13—C14	120.6 (2)
C2—C3—H3	119.7	C12—C13—H13	119.7
C4—C3—H3	119.7	C14—C13—H13	119.7
C3—C4—C5	120.1 (3)	C9—C14—C13	118.7 (2)
C3—C4—H4	120.0	C9—C14—C15	119.82 (19)
C5—C4—H4	120.0	C13—C14—C15	121.44 (18)
C6—C5—C4	120.0 (3)	C14—C15—S2	113.93 (12)
C6—C5—H5	120.0	C14—C15—H15A	108.8
C4—C5—H5	120.0	S2—C15—H15A	108.8
C5—C6—C1	118.3 (2)	C14—C15—H15B	108.8
C5—C6—C7	121.0 (2)	S2—C15—H15B	108.8
C1—C6—C7	120.6 (2)	H15A—C15—H15B	107.7
C6—C7—S1	108.00 (15)	N3—C16—N4	120.7 (2)
C6—C7—H7A	110.1	N3—C16—S2	115.7 (2)
S1—C7—H7A	110.1	N4—C16—S2	123.5 (2)
C6—C7—H7B	110.1	C16—N3—H3A	120.0
S1—C7—H7B	110.1	C16—N3—H3B	120.0
H7A—C7—H7B	108.4	H3A—N3—H3B	120.0
N1—C8—N2	121.5 (2)	C16—N4—H4A	120.0
N1—C8—S1	116.2 (2)	C16—N4—H4B	120.0
N2—C8—S1	122.3 (2)	H4A—N4—H4B	120.0
C16—S2—C15	104.82 (9)	Cl4—Zn1—Cl2	113.28 (2)
C8—N2—H2A	120.0	Cl4—Zn1—Cl3	103.76 (2)
C8—N2—H2B	120.0	Cl2—Zn1—Cl3	111.95 (2)
H2A—N2—H2B	120.0	Cl4—Zn1—Cl1	107.14 (2)
C10—C9—C14	119.7 (2)	Cl2—Zn1—Cl1	106.53 (2)
C10—C9—H9	120.1	Cl3—Zn1—Cl1	114.24 (3)

C6—C1—C2—C3	0.5 (4)	C14—C9—C10—C11	0.5 (4)
C1—C2—C3—C4	0.2 (5)	C9—C10—C11—C12	−0.7 (5)
C2—C3—C4—C5	−0.5 (5)	C10—C11—C12—C13	−0.2 (4)
C3—C4—C5—C6	−0.1 (4)	C11—C12—C13—C14	1.3 (4)
C4—C5—C6—C1	0.8 (4)	C10—C9—C14—C13	0.6 (3)
C4—C5—C6—C7	−179.1 (2)	C10—C9—C14—C15	179.8 (2)
C2—C1—C6—C5	−1.0 (4)	C12—C13—C14—C9	−1.5 (3)
C2—C1—C6—C7	178.9 (2)	C12—C13—C14—C15	179.3 (2)
C5—C6—C7—S1	−89.8 (2)	C9—C14—C15—S2	91.8 (2)
C1—C6—C7—S1	90.3 (2)	C13—C14—C15—S2	−89.0 (2)
C8—S1—C7—C6	165.34 (19)	C16—S2—C15—C14	81.90 (15)
C7—S1—C8—N1	−159.52 (19)	C15—S2—C16—N3	−159.78 (16)
C7—S1—C8—N2	20.0 (2)	C15—S2—C16—N4	22.5 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···Cl3	0.86	2.68	3.372 (2)	139
N1—H1B···Cl2ⁱ	0.86	2.45	3.255 (2)	157
N2—H2A···Cl4	0.86	2.53	3.219 (2)	138
N2—H2B···Cl3ⁱⁱ	0.86	2.62	3.262 (2)	132
N3—H3A···Cl1ⁱⁱⁱ	0.86	2.72	3.469 (2)	147
N3—H3A···Cl4ⁱⁱⁱ	0.86	2.65	3.244 (2)	128
N3—H3B···Cl1^iv	0.86	2.44	3.283 (2)	166
N4—H4A···Cl1ⁱⁱⁱ	0.86	2.49	3.290 (2)	156
N4—H4B···Cl2ⁱ	0.86	2.62	3.447 (2)	163
C15—H15A···S1	0.97	2.87	3.591 (2)	132
C15—H15A···Cl2^v	0.97	2.77	3.556 (2)	139
C15—H15B···Cl2ⁱ	0.97	2.65	3.594 (2)	164

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

Experimental details

Crystal data
Chemical formula	(C₈H₁₁N₂S)₂[ZnCl₄]
M_r	541.67
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	15.2135 (11), 6.4475 (5), 23.9277 (18)
β (°)	95.368 (1)
V (Å³)	2336.8 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.70
Crystal size (mm)	0.27 × 0.23 × 0.21

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	25129, 5481, 4986
R_int	0.026
(sin θ/λ)_max (Å⁻¹)	0.661

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.029, 0.073, 1.08
No. of reflections	5481
No. of parameters	244
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.41, −0.32

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), PLATON (Spek, 2003), SHELXL97 (Sheldrick, 2008) and PARST (Nardelli, 1995).

Selected bond lengths (Å) top

S1—C8	1.732 (2)	C16—N3	1.309 (2)
S1—C7	1.813 (2)	C16—N4	1.312 (2)
N1—C8	1.300 (3)	Cl1—Zn1	2.2792 (5)
C8—N2	1.300 (3)	Cl2—Zn1	2.2650 (5)
S2—C16	1.734 (2)	Cl3—Zn1	2.2718 (5)
S2—C15	1.825 (2)	Cl4—Zn1	2.2589 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···Cl3	0.86	2.68	3.372 (2)	138.5
N1—H1B···Cl2ⁱ	0.86	2.45	3.255 (2)	156.6
N2—H2A···Cl4	0.86	2.53	3.219 (2)	138.2
N2—H2B···Cl3ⁱⁱ	0.86	2.62	3.262 (2)	131.9
N3—H3A···Cl1ⁱⁱⁱ	0.86	2.72	3.469 (2)	146.5
N3—H3A···Cl4ⁱⁱⁱ	0.86	2.65	3.244 (2)	127.7
N3—H3B···Cl1^iv	0.86	2.44	3.283 (2)	165.5
N4—H4A···Cl1ⁱⁱⁱ	0.86	2.49	3.290 (2)	156.0
N4—H4B···Cl2ⁱ	0.86	2.62	3.447 (2)	162.5
C15—H15A···S1	0.97	2.87	3.591 (2)	131.8
C15—H15A···Cl2^v	0.97	2.77	3.556 (2)	138.7
C15—H15B···Cl2ⁱ	0.97	2.65	3.594 (2)	164.0

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

Acknowledgements

DG thanks the Council of Scientific and Industrial Research (CSIR), India, for a Senior Research Fellowship. Financial support from the University Grants Commission (UGC-SAP) and the Department of Science & Technology (DST-FIST), Government of India, is acknowledged by DV for providing facilities to the department.

References

Barker, J. & Powell, H. R. (1998). Acta Cryst. C54, 2019–2021. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Bruker (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Hemalatha, P., Veeravazhuthi, V., Mallika, J., Narayanadass, S. K. & Mangalaraj, D. (2006). Cryst. Res. Tech. 41, 775–779. Web of Science CrossRef CAS Google Scholar
Nardelli, M. (1995). J. Appl. Cryst. 28, 659. CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2003). J. Appl. Cryst. 36, 7–13. Web of Science CrossRef CAS IUCr Journals Google Scholar
Zhang, H. W., Batra, A. K. & Lal, R. B. (1994). J. Cryst. Growth. 137, 141–145. CrossRef CAS Web of Science Google Scholar