2-(5-Iodo-2-oxoindolin-3-yl-idene)hydrazinecarbo-thio-amide including an unknown solvate.

The mol-ecule of the title compound, C9H7IN4OS, is almost planar (r.m.s. deviation = 0.0373 Å). In the mol-ecule, N-H⋯N and N-H⋯O hydrogen bonds generate, respectively, S(5) and S(6) ring motifs. In the crystal, mol-ecules are linked via N-H⋯O hydrogen bonds, forming chains propagating along [010]. These chains are linked via S⋯I contacts [3.4915 (16) Å], forming sheets lying parallel to (100). A region of disordered electron density, probably a disordered tetra-hydro-furan solvent mol-ecule, was treated using the SQUEEZE routine in PLATON [Spek (2009). Acta Cryst. D65, 148-155]. The formula mass and unit-cell characteristics were not taken into account during refinement.

Related literature

For the synthesis, see: Chiyanzu et al. (2003 ▶). For applications, see: Silva et al. (2001 ▶); Chiyanzu et al. (2003 ▶). For similar structures, see: de Bittencourt et al. (2014 ▶); Bandeira et al. (2013 ▶); de Oliveira et al. (2012 ▶). For S⋯I inter­actions, see: Auffinger et al. (2004 ▶).

Experimental

Crystal data

C9H7IN4OS

M = 346.15

Monoclinic,

a = 33.765 (5) Å

b = 4.4569 (5) Å

c = 19.977 (3) Å

β = 123.100 (4)°

V = 2518.4 (6) Å3

Z = 8

Mo Kα radiation

μ = 2.69 mm−1

T = 100 K

1.15 × 0.10 × 0.09 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: numerical (SADABS; Bruker, 2009 ▶) T min = 0.701, T max = 0.777

18679 measured reflections

2892 independent reflections

2577 reflections with I > 2σ(I)

R int = 0.036

Refinement

R[F 2 > 2σ(F 2)] = 0.028

wR(F 2) = 0.062

S = 1.05

2892 reflections

161 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 1.50 e Å−3

Δρmin = −1.52 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); 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 ▶) and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S1600536814010782/bg2528sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814010782/bg2528Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814010782/bg2528Isup3.cml

CCDC reference: 1002200

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

C9H7IN4OS	F(000) = 1328
Mr = 346.15	Dx = 1.826 Mg m−3
Monoclinic, C2/c	Melting point: 522 K
Hall symbol: -C 2yc	Mo Kα radiation, λ = 0.71073 Å
a = 33.765 (5) Å	Cell parameters from 9997 reflections
b = 4.4569 (5) Å	θ = 2.4–28.3°
c = 19.977 (3) Å	µ = 2.69 mm−1
β = 123.100 (4)°	T = 100 K
V = 2518.4 (6) Å3	Needle, yellow
Z = 8	1.15 × 0.10 × 0.09 mm

Bruker APEXII CCD diffractometer	2892 independent reflections
Radiation source: fine-focus sealed tube	2577 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.036
φ and ω scans	θmax = 28.3°, θmin = 2.0°
Absorption correction: numerical (SADABS; Bruker, 2009)	h = −44→44
Tmin = 0.701, Tmax = 0.777	k = −3→5
18679 measured reflections	l = −26→26

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)] = 0.028	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.062	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ2(Fo2) + (0.0208P)2 + 10.8261P] where P = (Fo2 + 2Fc2)/3
2892 reflections	(Δ/σ)max = 0.001
161 parameters	Δρmax = 1.50 e Å−3
0 restraints	Δρmin = −1.52 e Å−3

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
C6	0.20209 (11)	0.5198 (5)	0.48073 (18)	0.0190 (6)
H6	0.2160	0.3772	0.4658	0.023*
C7	0.22592 (10)	0.6149 (6)	0.55978 (17)	0.0168 (5)
H7	0.2555	0.5382	0.5981	0.020*
C5	0.15782 (10)	0.6347 (6)	0.42365 (16)	0.0170 (6)
H41	0.2442 (12)	0.924 (7)	0.693 (2)	0.016 (8)*
H21	0.1270 (13)	1.502 (7)	0.631 (2)	0.023 (9)*
H11	0.0129 (12)	1.770 (7)	0.4600 (19)	0.019 (8)*
H12	0.0403 (15)	1.560 (9)	0.449 (3)	0.043 (12)*
I1	0.125098 (8)	0.47387 (4)	0.306159 (11)	0.02521 (7)
S1	0.06378 (3)	1.88628 (14)	0.62093 (4)	0.01889 (15)
O1	0.19376 (7)	1.3146 (4)	0.70372 (11)	0.0168 (4)
N4	0.22091 (9)	0.9605 (5)	0.65344 (15)	0.0145 (5)
N3	0.11031 (8)	1.3194 (4)	0.53273 (13)	0.0130 (4)
C9	0.18938 (9)	1.1590 (5)	0.64912 (16)	0.0137 (5)
C1	0.06744 (9)	1.6773 (5)	0.55453 (16)	0.0140 (5)
N1	0.03597 (10)	1.6699 (6)	0.47747 (15)	0.0209 (5)
C3	0.15944 (9)	0.9428 (5)	0.52186 (16)	0.0127 (5)
N2	0.10679 (9)	1.5041 (4)	0.58282 (15)	0.0145 (5)
C8	0.20411 (9)	0.8269 (5)	0.57920 (15)	0.0133 (5)
C2	0.14815 (9)	1.1580 (5)	0.56399 (15)	0.0127 (5)
C4	0.13579 (10)	0.8471 (5)	0.44356 (16)	0.0143 (5)
H4	0.1061	0.9222	0.4053	0.017*

	U11	U22	U33	U12	U13	U23
C6	0.0251 (17)	0.0160 (11)	0.0226 (17)	0.0021 (10)	0.0173 (14)	0.0005 (9)
C7	0.0115 (15)	0.0176 (11)	0.0198 (15)	0.0015 (9)	0.0076 (12)	0.0034 (9)
C5	0.0212 (16)	0.0181 (11)	0.0129 (15)	−0.0041 (10)	0.0101 (13)	−0.0011 (9)
I1	0.04097 (15)	0.02153 (9)	0.01480 (12)	−0.00098 (7)	0.01630 (11)	−0.00167 (6)
S1	0.0206 (4)	0.0199 (3)	0.0160 (4)	0.0050 (2)	0.0099 (3)	0.0011 (2)
O1	0.0125 (10)	0.0216 (9)	0.0106 (10)	−0.0011 (7)	0.0026 (8)	−0.0027 (7)
N4	0.0091 (13)	0.0177 (10)	0.0095 (13)	0.0006 (8)	0.0005 (11)	0.0010 (8)
N3	0.0119 (12)	0.0143 (9)	0.0125 (12)	−0.0011 (8)	0.0065 (10)	−0.0002 (7)
C9	0.0106 (14)	0.0153 (11)	0.0124 (14)	−0.0029 (9)	0.0044 (12)	0.0013 (9)
C1	0.0101 (14)	0.0154 (11)	0.0160 (15)	−0.0001 (9)	0.0068 (12)	0.0019 (9)
N1	0.0137 (14)	0.0276 (12)	0.0147 (14)	0.0078 (10)	0.0034 (11)	−0.0008 (9)
C3	0.0110 (14)	0.0139 (10)	0.0123 (14)	−0.0017 (9)	0.0057 (12)	0.0019 (8)
N2	0.0130 (13)	0.0168 (10)	0.0091 (13)	0.0007 (8)	0.0030 (10)	−0.0001 (8)
C8	0.0117 (14)	0.0144 (10)	0.0111 (14)	−0.0011 (9)	0.0044 (11)	0.0020 (9)
C2	0.0131 (14)	0.0135 (10)	0.0090 (13)	−0.0025 (9)	0.0043 (11)	0.0008 (8)
C4	0.0119 (14)	0.0159 (11)	0.0110 (14)	−0.0025 (9)	0.0036 (11)	0.0010 (9)

C6—C7	1.390 (4)	N3—C2	1.292 (3)
C6—C5	1.391 (4)	N3—N2	1.350 (3)
C6—H6	0.9300	C9—C2	1.498 (4)
C7—C8	1.378 (4)	C1—N1	1.309 (4)
C7—H7	0.9300	C1—N2	1.364 (3)
C5—C4	1.389 (4)	N1—H11	0.79 (3)
C5—I1	2.100 (3)	N1—H12	0.82 (4)
S1—C1	1.680 (3)	C3—C4	1.379 (4)
O1—C9	1.232 (3)	C3—C8	1.402 (4)
N4—C9	1.350 (3)	C3—C2	1.457 (3)
N4—C8	1.399 (3)	N2—H21	0.83 (4)
N4—H41	0.77 (3)	C4—H4	0.9300
C7—C6—C5	121.0 (2)	C1—N1—H11	118 (2)
C7—C6—H6	119.5	C1—N1—H12	119 (3)
C5—C6—H6	119.5	H11—N1—H12	122 (4)
C6—C7—C8	117.5 (3)	C4—C3—C8	120.7 (2)
C6—C7—H7	121.2	C4—C3—C2	133.3 (3)
C8—C7—H7	121.2	C8—C3—C2	105.9 (2)
C6—C5—C4	121.3 (2)	N3—N2—C1	119.9 (2)
C6—C5—I1	117.67 (19)	N3—N2—H21	121 (2)
C4—C5—I1	121.0 (2)	C1—N2—H21	119 (2)
C9—N4—C8	111.2 (2)	C7—C8—N4	128.4 (3)
C9—N4—H41	122 (2)	C7—C8—C3	121.6 (2)
C8—N4—H41	127 (2)	N4—C8—C3	110.0 (2)
C2—N3—N2	116.5 (2)	N3—C2—C3	126.1 (2)
O1—C9—N4	127.1 (3)	N3—C2—C9	127.4 (2)
O1—C9—C2	126.5 (2)	C3—C2—C9	106.5 (2)
N4—C9—C2	106.4 (2)	C3—C4—C5	117.8 (2)
N1—C1—N2	117.0 (2)	C3—C4—H4	121.1
N1—C1—S1	125.4 (2)	C5—C4—H4	121.1
N2—C1—S1	117.5 (2)
C5—C6—C7—C8	−0.1 (4)	C2—C3—C8—N4	−0.6 (3)
C7—C6—C5—C4	−0.3 (4)	N2—N3—C2—C3	179.7 (2)
C7—C6—C5—I1	−179.88 (19)	N2—N3—C2—C9	−2.1 (4)
C8—N4—C9—O1	−179.3 (2)	C4—C3—C2—N3	−1.1 (5)
C8—N4—C9—C2	−0.5 (3)	C8—C3—C2—N3	178.9 (2)
C2—N3—N2—C1	−178.7 (2)	C4—C3—C2—C9	−179.7 (3)
N1—C1—N2—N3	−4.7 (3)	C8—C3—C2—C9	0.3 (3)
S1—C1—N2—N3	176.33 (18)	O1—C9—C2—N3	0.4 (4)
C6—C7—C8—N4	−178.9 (2)	N4—C9—C2—N3	−178.4 (2)
C6—C7—C8—C3	0.3 (4)	O1—C9—C2—C3	179.0 (2)
C9—N4—C8—C7	−180.0 (2)	N4—C9—C2—C3	0.1 (3)
C9—N4—C8—C3	0.7 (3)	C8—C3—C4—C5	−0.4 (4)
C4—C3—C8—C7	0.0 (4)	C2—C3—C4—C5	179.5 (3)
C2—C3—C8—C7	−180.0 (2)	C6—C5—C4—C3	0.5 (4)
C4—C3—C8—N4	179.4 (2)	I1—C5—C4—C3	−179.85 (18)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H12···N3	0.85 (4)	2.28 (4)	2.633 (3)	105 (3)
N2—H21···O1	0.83 (4)	2.07 (4)	2.725 (3)	135 (3)
N4—H41···O1i	0.77 (3)	2.04 (4)	2.809 (3)	178 (3)
N1—H11···S1ii	0.79 (3)	2.66 (4)	3.448 (3)	170 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H12⋯N3	0.85 (4)	2.28 (4)	2.633 (3)	105 (3)
N2—H21⋯O1	0.83 (4)	2.07 (4)	2.725 (3)	135 (3)
N4—H41⋯O1i	0.77 (3)	2.04 (4)	2.809 (3)	178 (3)
N1—H11⋯S1ii	0.79 (3)	2.66 (4)	3.448 (3)	170 (3)

Symmetry codes: (i) ; (ii) .