untitled


European	Journal	of	Chemistry	3	(2)	(2012)	211‐213	

European	Journal	of	Chemistry	
ISSN	2153‐2249	(Print)	/	ISSN	2153‐2257	(Online)		2012	EURJCHEM	

DOI:10.5155/eurjchem.3.2.211‐213.594	

	
	

	

	

European	Journal	of	Chemistry	
Journal	homepage:	www.eurjchem.com	

	 	 	

Crystal	and	molecular	structure	of		
bis(4‐bromo‐N‐(di‐n‐butylcarbamothioyl)benzamido)	copper(II)	complex	

Gun	Binzeta,*,	Ulrich	Flörkeb,	Nevzat	Külcüc	and	Hakan	Arslanc	

a	Department	of	Chemistry,	Faculty	of	Education,	Mersin	University,	Mersin,	TR‐33169,	Turkey	
b	Department	of	Chemistry,	University	of	Paderborn,	Paderborn,	D‐33098,	Germany	
c	Department	of	Chemistry,	Faculty	of	Arts	and	Science,	Mersin	University,	Mersin,	TR‐33343,	Turkey	

*Corresponding	author	at:	Department	of	Chemistry,	Faculty	of	Education,	Mersin	University,	Mersin,	TR‐33169,	Turkey.	
Tel.:	+90.532.2701917;	fax:	+90.324.3610047.	E‐mail	address:	polatgun@gmail.com	(G.	Binzet).	

	
	

	 	

	 	 	
ARTICLE	INFORMATION	 	 ABSTRACT	
Received:	06	February	2012	
Received	in	revised	form:	13	February	2012	
Accepted:	13	February	2012	
Online:	30	June	2012	

KEYWORDS	

	 The	 title	 compound,	 C32H44Br2CuN4O2S2,	 was	 synthesized	 from	 4‐bromo‐N‐
(dibutylcarbamothioyl)benzamide	ligand	and	copper(II)acetate.	The	crystal	structure	of	bis(4‐
bromo‐N‐(di‐n‐butylcarbamothioyl)benzamido)	 copper(II)	 complex	 was	 determined	 from
single	 crystal	X‐ray	diffraction	studies.	 It	 crystallizes	 in	 the	triclinic	space	group,	P‐1	 (no.	2)
with	unit	 cell	 dimensions	 of	a	=	8.519(10)	Å,	b	=	16.64(2)	Å,	c	 =	 25.78(4)	Å,	α	 =	77.11(3)o,
β	=	85.59(3)o,	γ	=	89.46(2)o	,	Z	=	4	and	V	=	795.8(6)	Å3.	The	crystal	structure	is	stabilized	by
weak	C‐H…N,	C‐H…S	and	C‐H…Br	hydrogen‐bonding	interactions.	

Thiourea	
Benzamide	
Copper	complex	
Benzoylthiourea	
Crystal	structure	
Single	crystal	X‐ray	diffraction	

	
1.	Introduction	
	

The	 thiourea	 derivatives	 represent	 one	 of	 the	 most	
investigated	 classes	 of	 ligands	 in	 the	 coordination	 chemistry.	
They	 are	 versatile	 ligands	which	 can	 coordinate	 to	 transition	
metal	 centers	 either	 in	 monoanionic	 bidentate	 form	 or	 in	
neutral	form	[1‐4].	Thiourea	derivatives	such	as	N,N‐dialkyl‐N’‐
benzoylthiourea	 easily	 coordinate	 to	 a	 metal	 atom	 via	 both	
sulfur	and	oxygen	atoms	[5].	

Substituted	N,N‐dialkyl‐N'‐benzoylthioureas	are	interesting	
compounds	that	are	utilized	in	medicinal	as	antibacterial	[6‐8],	
antifungal	 [9,10],	 antiviral	 [11],	 pesticidal	 [12],	 cancerostatic	
[13]	 and	 cytotoxic	 [14]	 agents.	 In	 analytical	 chemistry,	
thioureas	 have	 been	 used	 as	 extraction	 agents	 for	 transition	
group	metal	 ions	[15].	In	addition,	 thioureas	are	also	useful	 in	
organic	 synthesis	 (Nitro‐Mannich	 reactions,	 Aza‐Henry	
reactions	and	Michael	addition	reactions)	[16].	

Our	 group	 is	 interested	 in	 the	 synthesis	 [5‐7,17‐23],	
characterization,	 crystal	 structure	 [24‐28],	 thermal	 behavior	
[29‐31]	 and	 antimicrobial	 activity	 [6‐7]	 of	 some	 substitute	
benzoylthiourea	 derivatives	 and	 their	 metal	 complexes.	 As	 a	
part	 of	 our	 ongoing	 studies	 into	 the	 structure	 and	 utility	 of	
sulfur	and	oxygen	containing	thiourea	derivative,	we	report	the	
crystal	 structure	 of	 bis(4‐bromo‐N‐(di‐n‐butylcarbamothioyl)	
benzamido)	copper(II)	complex.	
	
2.	Experimental	
	
2.1.	Instrumentation	
	

Single	 crystal	 X‐ray	 diffraction	 data	 were	 collected	 on	 a	
Bruker	AXS	SMART‐APEX	diffractometer	for	the	title	compound	
using	 monochromated	 MoK	 radiation.	 The	 structures	 were	

solved	 [32]	 by	 direct	 and	 conventional	 Fourier	methods	with	
full‐matrix	least‐squares	refinement	[32]	based	on	F².	All	apart	
from	 hydrogen	 atoms	 were	 refined	 anisotropically;	
geometrically	 placed	 hydrogen	 atoms	 were	 refined	 with	 a	
‘riding	model’	and	U(H)	=	1.2	U(Ciso)	and	1.5	U(Ciso)	for	methyl	
groups,	 respectively.	 SHELXTL	 [33],	 OLEX2	 [34]	 and	Mercury	
[35]	software	used	to	prepare	material	for	publication.	Further	
details	concerning	data	collection	and	refinement	are	given	 in	
Table	1.		

	
Table	1.	Crystal	data	and	structure	refinement	for	the	title	compound.	
Empirical	formula	 C32H44Br2CuN4O2S2	
Formula	weight	 804.19	
Temperature / K	 120(2)	
Space	group	 P‐1
a / Å,	b / Å,	c / Å		 8.519(10),	16.64(2),	25.78(4)	
α/°,	β/°,	γ/°	 77.11(3),	85.59(3),	89.46(2)
Volume / Å3		 3551(9)	
Z		 4	
ρcalc. / mg	mm‐3 1.504	
μ / mm‐1 3.017	
F(000)	 1644	
Crystal	size / mm3 0.40	×	0.10	×	0.03	
2Θ	range	for	data	collection	 2.66	to	55.74°	
Index	ranges	 ‐11	≤	h	≤	10,	‐21	≤	k	≤	21,	‐32	≤	l ≤	33
Reflections	collected	 30764	
Independent	reflections		 16654	[R(int)	=	0.2316]	
Data/restraints/parameters		 16654/0/775	
Goodness‐of‐fit	on	F2		 0.810	
Final	R	indexes	[I>2σ	(I)]	 R1	=	0.1077,	wR2	=	0.2208
Final	R	indexes	[all	data]		 R1	=	0.3127,	wR2	=	0.2859	
Largest	diff.	peak/hole / e	Å‐3 0.990/‐0.917	
	
	
	
	
	



212	 Binzet	et	al.	/	European	Journal	of	Chemistry	3	(2)	(2012)	211‐213	
	

	

	
	

Scheme	1
	

	
	

Figure	1.	A	perspective	view	of	the title	compound,	with	atom‐numbering	scheme.
	
	
2.2.	Synthesis	of	bis(4‐bromo‐N‐(di‐n‐butylcarbamothioyl)	
benzamido)	copper(II)	complex	
	

Bis(4‐bromo‐N‐(di‐n‐butylcarbamothioyl)benzamido)	
copper(II)	 complex	 was	 synthesized	 according	 to	 previously	
reported	method	[19].	A	solution	of	copper(II)acetate	(0.01	M)	
in	methanol	 (30	 cm3)	was	 added	dropwise	 to	 a	 solution	of	 4‐
bromo‐N‐(di‐n‐butylcarbamothioyl)benzamide	 in	 a	 1:2	 ratio	
(copper(II)acetate:4‐bromo‐N‐(di‐n‐butylcarbamothioyl)	 benz‐
amide)	 with	 a	 small	 excess	 of	 4‐bromo‐N‐(di‐n‐butylcarbamo	
thioyl)benzamide	 in	 ethanol	 (30	 cm3)	 at	 room	 temperature,	
and	 the	 resulting	 mixture	 was	 stirred	 for	 30	 min.	 The	 solid	
complex	 was	 filtered	 and	 recrystallized	 from	 an	
ethanol:dichloromethane	 mixture	 (1:2)	 (Scheme	 1).	 Green	
precipitate	was	formed	crystal	suitable	for	X‐ray	single	crystal	
diffraction.	 Bis(4‐bromo‐N‐(di‐n‐butylcarbamothioyl)benzami‐
do)	 copper(II):	 Yield:	 76%.	 M.p.:	 120‐122	 oC.	 Anal.	 calcd.	 for	
C32H44Br2N4O2S2Cu:	C,	47.79;	H,	5.51;	N,	6.97.	Found:	C,	48.08;	
H,	 5.44;	N,	7.04	%.	 FT‐IR	 (KBr,	 cm‐1):	 2954,	 2930,	 2864	 (CH),	
1579	(CN),	1493	(C‐O),	757	(C‐Br).	

	
3.	Results	and	discussion		
	

The	copper(II)	complex	was	synthesized	by	the	reaction	of	
4‐bromo‐N‐(di‐n‐butylcarbamothioyl)benzamide	 with	
[Cu(CH3COO)2].	 The	 compound	 was	 purified	 by	 re‐
crystallization	 from	 a	 ethanol:dichloromethane	 mixture	 (1:2)	
and	 characterized	 by	 elemental	 analysis	 and	 IR	 spectroscopy.	
The	 analytical	 and	 spectroscopic	 data	 are	 consistent	with	 the	
proposed	structure	given	in	Scheme	1.	

The	 structure	 of	 the	 title	 compound	 which	 is	 a	 typical	
benzoyl	 thiourea	 derivative	 was	 also	 confirmed	 by	
crystallographic	analyses.	There	are	two	independent	thiourea	
molecules	 in	 the	 asymmetric	 unit.	 The	molecular	 structure	 of	

the	 one	of	 the	 independent	molecules	 is	 depicted	 in	Figure	1,	
with	selected	bond	lengths	and	angles	provided	in	Table	2	and	
3.		

	
Table	2.	Bond	lengths	for	the	title	compound.		
Atom	 Atom	 Length/Å	 		 Atom	 Atom	 Length/Å	
Cu11 O12 1.932(9) Cu21	 O22	 1.898(10)
Cu11	 O11	 1.960(11)	 		 Cu21	 O21	 1.915(8)	
Cu11 S12 2.221(5) Cu21	 S22	 2.193(5)
Cu11	 S11	 2.221(5)	 		 Cu21	 S21	 2.231(5)	
Br11	 C114	 1.889(14)	 		 Br21	 C214	 1.916(14)	
Br12 C130 1.853(16) Br22	 C230	 1.884(14)
S11 C101 1.668(14) S21	 C201	 1.710(13)
S12 C117 1.733(13) S22	 C217	 1.691(15)
O11 C110 1.190(16) O21	 C210	 1.251(13)
O12 C126 1.225(16) O22	 C226	 1.236(14)
N11 C110 1.326(17) N21	 C210	 1.296(15)
N11 C101 1.357(17) N21	 C201	 1.340(15)
N12	 C101	 1.337(15)	 		 N22	 C201	 1.348(15)	
N12	 C102	 1.464(16)	 		 N22	 C202	 1.447(15)	
N12	 C106	 1.497(16)	 		 N22	 C206	 1.460(15)	
N13	 C126	 1.317(17)	 		 N23	 C226	 1.314(15)	
N13 C117 1.338(16) N23	 C217	 1.334(16)
N14 C117 1.283(15) N24	 C217	 1.339(17)
N14 C118 1.454(15) N24	 C218	 1.441(16)
	

The	 copper	 atom	 is	 in	 four‐coordination	 geometry	
contributed	 by	 two	 oxygen	 and	 two	 sulfur	 atoms.	 The	 S(12)‐
Cu(11)‐O(11)	bond	angle	is	162.8(3)o	and	that	of	S(11)‐Cu(11)‐
O(12)	 164.6(3)o.	 	 The	 Cu(11)‐S(11)	 and	 Cu(11)‐S(12)	 bond	
lengths	 are	 2.221(5)	 Å	 and	 2.221(5)	 Å,	 respectively,	 and	
Cu(11)‐O(11)	and	Cu(11)‐O(12)	bond	 lengths	are	1.960(11)	Å	
and	 1.932(9)	 	 Å,	 respectively.	 These	 bond	 distances	 are	 very	
similar	to	the	literature	[18‐23,36‐39].	

The	 dihedral	 angle	 between	 S(11)Cu(11)O(11)	 plane	 and	
S(12)Cu(11)O(12)	plane	is	21.74(13)o.	 	The	bond	length	of	the	
thiocarbonyl					S(12)‐C(117)					1.733(13)					Å;					S(11)‐C(101)		



Binzet		et	al.	/	European	Journal	of	Chemistry	3	(2)	(2012)	211‐213	 213	
 

Table	3.	Bond	angles	for	the	title	compound.		
Atom	 Atom	 Atom	 Angle	(˚)	 		 Atom	 Atom	 Atom	 Angle	(˚)	
O12	 Cu11	 O11	 84.0(4)	 		 O22	 Cu21	 O21 85.2(4)
O12	 Cu11	 S12	 94.8(3)	 		 O22	 Cu21	 S22 94.1(3)
O11	 Cu11	 S12	 162.8(3)	 		 O21	 Cu21	 S22	 168.7(3)	
O12	 Cu11	 S11	 164.6(3)	 		 O22	 Cu21	 S21	 168.7(3)	
O11	 Cu11	 S11	 94.9(3)	 		 O21	 Cu21	 S21	 93.6(3)	
S12	 Cu11	 S11	 90.74(19)	 		 S22	 Cu21	 S21	 89.29(19)	
C101	 S11	 Cu11	 106.5(6)	 		 C201	 S21	 Cu21 106.9(5)
C117	 S12	 Cu11	 107.8(5)	 		 C217	 S22	 Cu21 107.8(6)
C110	 O11	 Cu11	 129.0(10)	 		 C210	 O21	 Cu21 132.9(9)
C126	 O12	 Cu11	 129.3(10)	 		 C226	 O22	 Cu21 131.5(10)
C110	 N11	 C101	 125.3(13)	 		 C210	 N21	 C201 125.1(11)
C101	 N12	 C102	 123.3(12)	 		 C201	 N22	 C202 125.4(11)
C101	 N12	 C106	 121.2(13)	 		 C201	 N22	 C206 119.4(11)
C102	 N12	 C106	 115.5(11)	 		 C202	 N22	 C206	 115.2(10)	
C126	 N13	 C117	 127.5(12)	 		 C226	 N23	 C217 122.0(12)
C117	 N14	 C118	 126.3(12)	 		 C217	 N24	 C218	 122.3(14)	
C117	 N14	 C122	 119.6(12)	 		 C217	 N24	 C222	 122.3(12)	
C118	 N14	 C122	 114.0(11)	 		 C218	 N24	 C222 112.5(12)
N12	 C101	 N11	 113.2(13)	 		 N21	 C201	 N22 114.8(11)
N12	 C101	 S11	 119.0(12)	 		 N21	 C201	 S21 130.1(10)
N11	 C101	 S11	 127.7(10)	 		 N22	 C201	 S21 115.2(11)
O11	 C110	 N11	 132.4(15)	 		 O21	 C210	 N21 130.3(13)
O11	 C110	 C111	 114.8(15)	 		 O21	 C210	 C211 112.9(13)
N11	 C110	 C111	 112.8(14)	 		 N21	 C210	 C211 116.9(12)
N14	 C117	 N13	 114.7(12)	 		 N23	 C217	 N24	 111.2(13)	
N14	 C117	 S12	 118.9(12)	 		 N23	 C217	 S22	 130.4(12)	
N13	 C117	 S12	 126.3(11)	 		 N24	 C217	 S22	 118.2(13)	
C132	 C127	 C128	 116.3(14)	 		 C228	 C227	 C232	 116.2(14)	
C132	 C127	 C126	 120.1(13)	 		 C228	 C227	 C226 123.6(14)
C128	 C127	 C126	 123.6(14)	 		 C232	 C227	 C226 120.2(12)
	
Table	4.	Hydrogen	bonds	for	the	title	compound.	
D	 H	 A	 d(D‐H)	(Å)	 d(H‐A)	(Å)	 d(D‐A) (Å) D‐H‐A (°)
C102	 H10A	 S11	 0.99	 2.51	 2.960(15)	 107	
C106	 H10I	 S21i	 0.99	 2.83	 3.606(18) 136
C107	 H10L	 N11	 0.99	 2.60	 3.11(2)	 112	
C118	 H11E	 S12	 0.99	 2.53	 3.004(14)	 109	
C123	 H12H	 Br21ii	 0.99	 2.82	 3.538(14) 130
C123	 H12I	 N13	 0.99	 2.56	 3.056(18) 111
C202	 H20B	 S21	 0.99	 2.47	 2.936(15) 108
C216	 H21D	 N21	 0.95	 2.42	 2.75(2) 100
Symmetry	codes:	i:	1‐x,1‐y,1‐z;	ii:	x,	‐1+y,	z.	
	
1.668(14)	 Å	 and	 carbonyl	 O(12)‐C(126)	 1.225(16);	 O(11)‐
C(110)	1.190(16)	Å	bonds	are	longer	than	the	average	for	C=S	
and	 C=O,	 while	 the	 C‐N	 bonds	 in	 the	 complex	 ring	 are	 all	
shorter	than	the	average	for	C‐N	single	bonds	(1.48	Å)	[18‐23].	
These	 results	 indicate	 extensive	 delocalization	 in	 the	 chelate	
ring	 [18‐23].	 All	 the	 other	 bond	 lengths	 are	 in	normal	 ranges	
[40].	

The	 crystal	 structure	 is	 stabilized	by	weak	C‐H…N,	C‐H…S	
and	C‐H…Br	hydrogen‐bonding	interactions	(Table	4).		
	
4.	Conclusion	
	

In	 this	 study,	 bis(4‐bromo‐N‐(di‐n‐butylcarbamothioyl)	
benzamido)	 copper(II)	 complex	 was	 synthesized	 and	 the	
crystal	 structure	 of	 copper	 complex	 was	 determined	 from	
single	crystal	X‐ray	diffraction	studies.	
	
Acknowledgements	

	
This	 work	 was	 supported	 by	 Mersin	 University	 Research	

Fund	(Project	No:	BAP‐FBE‐KB(GB)‐2006‐1).	
	

Supplementary	material	
	

CCDC‐848931	contains	the	supplementary	crystallographic	
data	 for	 this	paper.	These	data	can	be	obtained	 free	of	charge	
via	 www.ccdc.cam.ac.uk/data_request/cif,	 or	 by	 e‐mailing	
data_request@ccdc.cam.ac.uk,	or	by	contacting	The	Cambridge	
Crystallographic	 Data	 Centre,	 12	 Union	 Road,	 Cambridge	 CB2	
1EZ,	UK;	fax:	+44(0)1223‐336033.	
	
	
	

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