1-(5-Bromo-2-oxoindolin-3-yl­idene)thio­semicarbazide acetonitrile monosolvate

Pederzolli, F.R.S.; Bresolin, L.; Carratu, V.S.; Locatelli, A.; Oliveira, A.B. de

doi:10.1107/S1600536811023786

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Volume 67| Part 7| July 2011| Page o1804

doi:10.1107/S1600536811023786

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1-(5-Bromo-2-oxoindolin-3-ylidene)thiosemicarbazide acetonitrile monosolvate

Fernanda Rosi Soares Pederzolli,^a Leandro Bresolin,^a ^* Vanessa Santana Carratu,^a Aline Locatelli ^b and Adriano Bof de Oliveira ^c

^aEscola de Química e Alimentos, Universidade Federal do Rio Grande, Av. Itália km 08, Campus Carreiros, 96201-900 Rio Grande, RS, Brazil, ^bDepartamento de Química, Universidade Federal de Santa Maria, Av. Roraima, Campus, 97105-900 Santa Maria, RS, Brazil, and ^cDepartamento de Química, Universidade Federal de Sergipe, Av. Marechal Rondon s/n, Campus, 49100-000 São Cristóvão-SE, Brazil
^*Correspondence e-mail: leandro_bresolin@yahoo.com.br

(Received 9 June 2011; accepted 17 June 2011; online 25 June 2011)

In the crystal structure of the title compound, C₉H₇BrN₄OS·C₂H₃N, the molecules are connected via N—H⋯O and N—H⋯S interactions into zigzag chains perpendicular to [001]. The molecules in these chains are additionally linked to acetonitrile solvent molecules through N—H⋯N hydrogen bonding. The molecules are arranged in layers and are stacked in the direction of the c axis indicative of π–π interactions, with distance = 3.381 (7) Å for the C⋯C interaction parallel to [001]. An intramolecular N—H⋯O hydrogen bond is also observed in the main molecule.

Related literature

For the pharmacological properties of isatin-thiosemicarbazone derivatives against cruzain, falcipain-2 and rhodesain, see: Chiyanzu et al. (2003 ). For the synthesis of 5-bromoisatin-3-thiosemicarbazone, see: Campaigne & Archer (1952 ).

Experimental

Crystal data

C₉H₇BrN₄OS·C₂H₃N
M_r = 340.21
Monoclinic, C 2/c
a = 20.017 (4) Å
b = 13.352 (2) Å
c = 13.190 (5) Å
β = 129.258 (2)°
V = 2729.6 (12) Å³
Z = 8
Mo Kα radiation
μ = 3.16 mm⁻¹
T = 293 K
0.22 × 0.20 × 0.16 mm

Data collection

Bruker CCD X8 APEXII diffractometer
10884 measured reflections
3377 independent reflections
2754 reflections with I > 2σ(I)
R_int = 0.030

Refinement

R[F² > 2σ(F²)] = 0.039
wR(F²) = 0.105
S = 1.09
3377 reflections
173 parameters
H-atom parameters constrained
Δρ_max = 1.03 e Å⁻³
Δρ_min = −0.86 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H5⋯O	0.86	2.10	2.769 (3)	134
N4—H6⋯N5	0.86	2.61	3.438 (5)	161
N4—H7⋯Oⁱ	0.86	2.05	2.906 (4)	173
N1—H4⋯Sⁱⁱ	0.86	2.50	3.350 (3)	169
Symmetry codes: (i) $[x-{\script{1\over 2}}, -y-{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (ii) $[x+{\script{1\over 2}}, -y-{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2006 ); cell refinement: SAINT (Bruker, 2003 ); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2006 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811023786/nc2233sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811023786/nc2233Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811023786/nc2233Isup3.cml

checkCIF report

Comment top

Thiosemicarbazone derivatives have a wide range of biological properties. For example, isatin-based synthetic thiosemicarbazones show pharmacological activity against cruzain, falcipain-2 and rhodesain (Chiyanzu et al., 2003). As part of our study of thiosemicarbazone derivatives, we report herein the crystal structure of 5-Bromoisatin-3-thiosemicarbazone acetonitrile solvate.

The crystal structure of the title compound is build of one-dimensional zigzag chain in which the molecules are linked by pairs of N—H···O and N—H···S hydrogen bonding. Each two molecules within these chains are additionally linked by acetonitrile molecules via N—H···N hydrogen bonding and weak C—H···S interactions. The molecules are arranged in layers and are stacked into the direction of the c-axis indicative for π-π-interactions.

Related literature top

For the pharmacological properties of isatin-thiosemicarbazone derivatives against cruzain, falcipain-2 and rhodesain, see: Chiyanzu et al. (2003). For the synthesis of 5-bromoisatin-3-thiosemicarbazone, see: Campaigne & Archer (1952).

Experimental top

Starting materials were commercially available and were used without further purification. The synthesis was adapted from a procedure reported previously (Campaigne & Archer, 1952). The hydrochloric acid catalyzed reaction of 5-bromoisatin (8,83 mmol) and thiosemicarbazide (8,83 mmol) in ethanol (50 ml) was refluxed for 6 h. After cooling and filtering, crystals suitable for X-ray diffraction were obtained from an acetonitrile solution.

Computing details top

Data collection: APEX2 (Bruker, 2006); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT (Bruker, 2003); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

	Fig. 1. : The molecular structure of the title compound with labelling and displacement ellipsoids drawn at the 50% probability level.
	Fig. 2. : Crystal structure of the title compound viewed in the direction of the crystallographic c axis. Hydrogen bonding is indicated as dashed lines.

1-(5-Bromo-2-oxoindolin-3-ylidene)thiosemicarbazide acetonitrile monosolvate top

Crystal data top

C₉H₇BrN₄OS·C₂H₃N	F(000) = 1360
M_r = 340.21	D_x = 1.656 Mg m⁻³
Monoclinic, C2/c	Melting point: 544.15 K
Hall symbol: -C 2yc	Mo Kα radiation, λ = 0.71073 Å
a = 20.017 (4) Å	Cell parameters from 3718 reflections
b = 13.352 (2) Å	θ = 2.6–27.6°
c = 13.190 (5) Å	µ = 3.16 mm⁻¹
β = 129.258 (2)°	T = 293 K
V = 2729.6 (12) Å³	Block, yellow
Z = 8	0.22 × 0.20 × 0.16 mm

Data collection top

Bruker CCD X8 APEXII diffractometer	2754 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube, Bruker CCD X8 APEXII	R_int = 0.030
Graphite monochromator	θ_max = 28.3°, θ_min = 2.0°
ϕ and ω scans	h = −26→14
10884 measured reflections	k = −16→17
3377 independent reflections	l = −7→17

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.105	H-atom parameters constrained
S = 1.09	w = 1/[σ²(F_o²) + (0.0396P)² + 12.0809P] where P = (F_o² + 2F_c²)/3
3377 reflections	(Δ/σ)_max < 0.001
173 parameters	Δρ_max = 1.03 e Å⁻³
0 restraints	Δρ_min = −0.86 e Å⁻³

Crystal data top

C₉H₇BrN₄OS·C₂H₃N	V = 2729.6 (12) Å³
M_r = 340.21	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 20.017 (4) Å	µ = 3.16 mm⁻¹
b = 13.352 (2) Å	T = 293 K
c = 13.190 (5) Å	0.22 × 0.20 × 0.16 mm
β = 129.258 (2)°

Data collection top

Bruker CCD X8 APEXII diffractometer	2754 reflections with I > 2σ(I)
10884 measured reflections	R_int = 0.030
3377 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	0 restraints
wR(F²) = 0.105	H-atom parameters constrained
S = 1.09	w = 1/[σ²(F_o²) + (0.0396P)² + 12.0809P] where P = (F_o² + 2F_c²)/3
3377 reflections	Δρ_max = 1.03 e Å⁻³
173 parameters	Δρ_min = −0.86 e Å⁻³

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
C9	0.3611 (2)	−0.2695 (2)	0.4897 (3)	0.0175 (6)
C10	0.0960 (2)	−0.0277 (3)	0.2196 (3)	0.0297 (8)
H8	0.0967	−0.0995	0.2159	0.045*
H9	0.0735	−0.0003	0.1361	0.045*
H10	0.0602	−0.0075	0.2410	0.045*
C11	0.1832 (2)	0.0088 (3)	0.3192 (4)	0.0296 (8)
C6	0.52345 (19)	0.0354 (2)	0.6478 (3)	0.0166 (6)
C5	0.4655 (2)	0.1144 (2)	0.5889 (3)	0.0169 (6)
H3	0.4062	0.1038	0.5301	0.020*
C4	0.5007 (2)	0.2109 (2)	0.6225 (3)	0.0205 (6)
C3	0.5890 (2)	0.2282 (2)	0.7097 (3)	0.0214 (7)
H2	0.6101	0.2934	0.7300	0.026*
C2	0.6469 (2)	0.1459 (3)	0.7675 (3)	0.0224 (7)
H1	0.7063	0.1558	0.8254	0.027*
C1	0.6126 (2)	0.0514 (2)	0.7353 (3)	0.0181 (6)
C8	0.5995 (2)	−0.1188 (3)	0.7243 (3)	0.0191 (6)
C7	0.51065 (19)	−0.0725 (2)	0.6367 (3)	0.0152 (6)
Br	0.42473 (2)	0.32205 (3)	0.54837 (4)	0.02739 (12)
N2	0.43754 (17)	−0.1178 (2)	0.5672 (2)	0.0171 (5)
N3	0.43806 (16)	−0.2191 (2)	0.5678 (2)	0.0174 (5)
H5	0.4860	−0.2515	0.6165	0.021*
N4	0.29129 (18)	−0.2149 (2)	0.4244 (3)	0.0217 (6)
H6	0.2951	−0.1507	0.4317	0.026*
H7	0.2414	−0.2430	0.3741	0.026*
N5	0.2515 (2)	0.0381 (3)	0.3981 (4)	0.0491 (10)
N1	0.65560 (17)	−0.0418 (2)	0.7786 (3)	0.0197 (5)
H4	0.7108	−0.0486	0.8329	0.024*
O	0.61642 (14)	−0.20772 (17)	0.7432 (2)	0.0200 (5)
S	0.36470 (5)	−0.39515 (6)	0.48661 (8)	0.02291 (19)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C9	0.0139 (15)	0.0224 (17)	0.0165 (14)	−0.0033 (12)	0.0098 (13)	−0.0014 (12)
C10	0.0273 (19)	0.0265 (19)	0.0264 (18)	−0.0018 (15)	0.0126 (16)	−0.0003 (15)
C11	0.0214 (18)	0.0231 (18)	0.035 (2)	0.0042 (14)	0.0134 (17)	0.0086 (15)
C6	0.0129 (14)	0.0219 (16)	0.0136 (14)	−0.0017 (12)	0.0077 (12)	−0.0009 (12)
C5	0.0157 (15)	0.0187 (15)	0.0156 (14)	0.0004 (12)	0.0097 (13)	0.0004 (12)
C4	0.0239 (17)	0.0175 (16)	0.0227 (16)	0.0048 (13)	0.0160 (15)	0.0041 (13)
C3	0.0248 (17)	0.0163 (16)	0.0259 (17)	−0.0049 (13)	0.0173 (15)	−0.0006 (13)
C2	0.0138 (15)	0.0238 (17)	0.0244 (17)	−0.0037 (13)	0.0096 (14)	−0.0032 (13)
C1	0.0149 (15)	0.0230 (16)	0.0164 (14)	−0.0006 (12)	0.0099 (13)	−0.0005 (12)
C8	0.0124 (15)	0.0271 (18)	0.0147 (14)	−0.0001 (13)	0.0072 (13)	0.0000 (12)
C7	0.0119 (14)	0.0188 (15)	0.0128 (13)	0.0001 (11)	0.0068 (12)	−0.0005 (11)
Br	0.0271 (2)	0.01948 (18)	0.0320 (2)	0.00440 (14)	0.01693 (16)	0.00453 (14)
N2	0.0164 (13)	0.0179 (13)	0.0172 (13)	0.0003 (10)	0.0107 (12)	0.0007 (10)
N3	0.0101 (12)	0.0179 (13)	0.0187 (13)	0.0011 (10)	0.0066 (11)	0.0003 (10)
N4	0.0130 (13)	0.0167 (13)	0.0283 (15)	−0.0002 (11)	0.0097 (12)	0.0017 (11)
N5	0.0247 (19)	0.046 (2)	0.052 (2)	−0.0026 (16)	0.0130 (18)	0.0101 (19)
N1	0.0110 (12)	0.0191 (14)	0.0223 (13)	−0.0005 (10)	0.0073 (11)	−0.0002 (11)
O	0.0133 (11)	0.0176 (11)	0.0212 (11)	0.0014 (9)	0.0072 (10)	0.0005 (9)
S	0.0140 (4)	0.0176 (4)	0.0273 (4)	0.0001 (3)	0.0084 (3)	0.0001 (3)

Geometric parameters (Å, º) top

C9—N4	1.305 (4)	C3—C2	1.419 (5)
C9—N3	1.370 (4)	C3—H2	0.9300
C9—S	1.681 (3)	C2—C1	1.369 (5)
C10—C11	1.451 (5)	C2—H1	0.9300
C10—H8	0.9600	C1—N1	1.412 (4)
C10—H9	0.9600	C8—O	1.217 (4)
C10—H10	0.9600	C8—O	1.217 (4)
C11—N5	1.142 (5)	C8—N1	1.346 (4)
C11—N5	1.142 (5)	C8—C7	1.510 (4)
C6—C5	1.386 (4)	C7—N2	1.285 (4)
C6—C1	1.398 (4)	N2—N3	1.352 (4)
C6—C7	1.455 (4)	N3—H5	0.8600
C5—C4	1.399 (5)	N4—H6	0.8600
C5—H3	0.9300	N4—H7	0.8600
C4—C3	1.389 (5)	N1—H4	0.8600
C4—Br	1.894 (3)

N4—C9—N3	116.5 (3)	C1—C2—H1	121.0
N4—C9—S	125.9 (2)	C3—C2—H1	121.0
N3—C9—S	117.6 (2)	C2—C1—C6	121.6 (3)
C11—C10—H8	109.5	C2—C1—N1	129.0 (3)
C11—C10—H9	109.5	C6—C1—N1	109.4 (3)
H8—C10—H9	109.5	O—C8—O	0.00 (5)
C11—C10—H10	109.5	O—C8—N1	127.3 (3)
H8—C10—H10	109.5	O—C8—N1	127.3 (3)
H9—C10—H10	109.5	O—C8—C7	126.6 (3)
N5—C11—N5	0.0 (8)	O—C8—C7	126.6 (3)
N5—C11—C10	179.2 (5)	N1—C8—C7	106.1 (3)
N5—C11—C10	179.2 (5)	N2—C7—C6	125.9 (3)
C5—C6—C1	121.7 (3)	N2—C7—C8	127.7 (3)
C5—C6—C7	131.7 (3)	C6—C7—C8	106.3 (3)
C1—C6—C7	106.6 (3)	C7—N2—N3	117.8 (3)
C6—C5—C4	116.6 (3)	N2—N3—C9	119.0 (3)
C6—C5—H3	121.7	N2—N3—H5	120.5
C4—C5—H3	121.7	C9—N3—H5	120.5
C3—C4—C5	122.5 (3)	C9—N4—H6	120.0
C3—C4—Br	118.8 (3)	C9—N4—H7	120.0
C5—C4—Br	118.6 (2)	H6—N4—H7	120.0
C4—C3—C2	119.6 (3)	C8—N1—C1	111.6 (3)
C4—C3—H2	120.2	C8—N1—H4	124.2
C2—C3—H2	120.2	C1—N1—H4	124.2
C1—C2—C3	117.9 (3)

C1—C6—C5—C4	−0.6 (4)	O—C8—C7—N2	0.2 (5)
C7—C6—C5—C4	−180.0 (3)	N1—C8—C7—N2	−178.7 (3)
C6—C5—C4—C3	0.3 (4)	O—C8—C7—C6	179.1 (3)
C6—C5—C4—Br	−178.6 (2)	O—C8—C7—C6	179.1 (3)
C5—C4—C3—C2	0.3 (5)	N1—C8—C7—C6	0.2 (3)
Br—C4—C3—C2	179.2 (2)	C6—C7—N2—N3	179.4 (3)
C4—C3—C2—C1	−0.7 (5)	C8—C7—N2—N3	−1.9 (4)
C3—C2—C1—C6	0.4 (5)	C7—N2—N3—C9	−176.9 (3)
C3—C2—C1—N1	179.9 (3)	N4—C9—N3—N2	−3.6 (4)
C5—C6—C1—C2	0.3 (5)	S—C9—N3—N2	176.5 (2)
C7—C6—C1—C2	179.8 (3)	C10—C11—N5—N5	0 (12)
C5—C6—C1—N1	−179.3 (3)	O—C8—N1—C1	−179.0 (3)
C7—C6—C1—N1	0.2 (3)	O—C8—N1—C1	−179.0 (3)
C5—C6—C7—N2	−1.8 (5)	C7—C8—N1—C1	−0.1 (3)
C1—C6—C7—N2	178.7 (3)	C2—C1—N1—C8	−179.6 (3)
C5—C6—C7—C8	179.2 (3)	C6—C1—N1—C8	0.0 (3)
C1—C6—C7—C8	−0.2 (3)	N1—C8—O—O	0.0 (2)
O—C8—C7—N2	0.2 (5)	C7—C8—O—O	0.00 (11)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H5···O	0.86	2.10	2.769 (3)	134
N4—H6···N5	0.86	2.61	3.438 (5)	161
N4—H7···Oⁱ	0.86	2.05	2.906 (4)	173
N1—H4···Sⁱⁱ	0.86	2.50	3.350 (3)	169

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

Experimental details

Crystal data
Chemical formula	C₉H₇BrN₄OS·C₂H₃N
M_r	340.21
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	293
a, b, c (Å)	20.017 (4), 13.352 (2), 13.190 (5)
β (°)	129.258 (2)
V (Å³)	2729.6 (12)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	3.16
Crystal size (mm)	0.22 × 0.20 × 0.16

Data collection
Diffractometer	Bruker CCD X8 APEXII diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	10884, 3377, 2754
R_int	0.030
(sin θ/λ)_max (Å⁻¹)	0.668

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.105, 1.09
No. of reflections	3377
No. of parameters	173
H-atom treatment	H-atom parameters constrained
	w = 1/[σ²(F_o²) + (0.0396P)² + 12.0809P] where P = (F_o² + 2F_c²)/3
Δρ_max, Δρ_min (e Å⁻³)	1.03, −0.86

Computer programs: APEX2 (Bruker, 2006), SAINT (Bruker, 2003), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg, 2006), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H5···O	0.86	2.10	2.769 (3)	134
N4—H6···N5	0.86	2.61	3.438 (5)	161
N4—H7···Oⁱ	0.86	2.05	2.906 (4)	173
N1—H4···Sⁱⁱ	0.86	2.50	3.350 (3)	169

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

Acknowledgements

We gratefully acknowledge Professor Dr Manfredo Hörner (Department of Chemistry, Federal University of Santa Maria, Brazil) for his help and support with the X-ray measurements, and CNPq/FAPERGS for financial support.

References

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doi:10.1107/S1600536811023786

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

1-(5-Bromo-2-oxoindolin-3-yl­­idene)thio­semicarbazide aceto­nitrile monosolvate

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

1-(5-Bromo-2-oxoindolin-3-ylidene)thiosemicarbazide acetonitrile monosolvate