1,5-Bis(2-oxoindolin-3-yl­idene)thio­carbonohydrazide tetra­hydro­furan monosolvate

Pezeshkpour, S.; Khaledi, H.; Mohd Ali, H.

doi:10.1107/S1600536812022714

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 6| June 2012| Page o1870

doi:10.1107/S1600536812022714

Open

access

1,5-Bis(2-oxoindolin-3-ylidene)thiocarbonohydrazide tetrahydrofuran monosolvate

Shaghayegh Pezeshkpour,^a Hamid Khaledi ^a ^* and Hapipah Mohd Ali ^a

^aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: hamid.khaledi@gmail.com

(Received 16 May 2012; accepted 18 May 2012; online 23 May 2012)

In the thiocarbonohydrazide molecule of the title compound, C₁₇H₁₂N₆O₂S·C₄H₈O, the terminal indolin-2-one ring systems make a dihedral angle of 20.13 (6)° with each other. Two intramolecular N—H⋯O hydrogen bonds are present, each of which generates an S(6) ring. In the crystal, N—H⋯O hydrogen bonds lead to a molecular chain running along the b axis. The tetrahydrofuran solvent molecule is disordered over two orientations in a 0.561 (11):0.439 (11) ratio.

Related literature

For the structures of the N-methylisatin analogue and its Sn(IV) complex and also the spectroscopic characterization of the title thiocarbonohydrazide, see: Bacchi et al. (2005 ).

Experimental

Crystal data

C₁₇H₁₂N₆O₂S·C₄H₈O
M_r = 436.49
Triclinic, $[P \overline 1]$
a = 8.4768 (1) Å
b = 11.4765 (2) Å
c = 11.9091 (2) Å
α = 75.206 (1)°
β = 72.553 (1)°
γ = 69.416 (1)°
V = 1020.02 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.20 mm⁻¹
T = 296 K
0.33 × 0.25 × 0.13 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.938, T_max = 0.975
9421 measured reflections
4451 independent reflections
3628 reflections with I > 2σ(I)
R_int = 0.016

Refinement

R[F² > 2σ(F²)] = 0.040
wR(F²) = 0.121
S = 1.05
4451 reflections
338 parameters
30 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.28 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O3ⁱ	0.88 (1)	1.96 (2)	2.829 (15)	168 (2)
N1—H1⋯O3′ⁱ	0.88 (1)	1.98 (3)	2.84 (2)	167 (2)
N3—H3⋯O1	0.85 (1)	2.18 (2)	2.8369 (16)	134 (2)
N4—H4⋯O2	0.86 (1)	2.10 (2)	2.7857 (16)	136 (2)
N6—H6⋯O1ⁱⁱ	0.84 (1)	2.32 (2)	3.0522 (16)	146 (2)
Symmetry codes: (i) x, y-1, z; (ii) x, y+1, z.

Data collection: APEX2 (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001 ); software used to prepare material for publication: SHELXL97 and publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812022714/is5142sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812022714/is5142Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812022714/is5142Isup3.cml

checkCIF report

Comment top

Recently, a series of isatin-based thiocarbonohydrazides and the related Sn(IV) complexes were synthesized and studied for their antimicrobial and mutagenic properties (Bacchi et al., 2005). The title compound, being among those, was re-synthesized and grown as X-ray quality crystals from THF by our research group. In the crystal structure, the hydrazone molecule is roughly planar with the maximum deviation from the least-squares plane of all non-H atoms being 0.481 (2) Å for atom C14. The configurations around the C—N bonds, stabilized by intramolecular N—H···O hydrogen bonding (Table 1), are same as those observed in the N-methylisatin analogous. The hydrazone molecule is co-crystallized with one molecule of THF which suffers from disorder. The crystal packing contains chains along the b axis formed by intermolecular N6—H6···O1 hydrogen bonds (Table 1 and Fig. 2). The THF molecules are N—H···O bonded to the chain.

Related literature top

For the structures of the N-methylisatin analogue and its Sn(IV) complex and also the spectroscopic characterization of the title thiocarbonohydrazide, see: Bacchi et al. (2005).

Experimental top

The Schiff base was prepared as described previously (Bacchi et al., 2005) and grown as X-ray quality crystals from a THF solution at room temperature.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and publCIF (Westrip, 2010).

Figures top

	Fig. 1. Displacement ellipsoid plot of the title compound at the 30% probability level. Hydrogen atoms are drawn as spheres of arbitrary radius. Only the major component of the disordered tetrahydrofuran molecule is shown.
	Fig. 2. A packing diagram, showing the N—H···O hydrogen bonded chain along the b axis. Hydrogen bonds are depicted as red dashed lines.

1,5-Bis(2-oxoindolin-3-ylidene)thiocarbonohydrazide tetrahydrofuran monosolvate top

Crystal data top

C₁₇H₁₂N₆O₂S·C₄H₈O	Z = 2
M_r = 436.49	F(000) = 456
Triclinic, P1	D_x = 1.421 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.4768 (1) Å	Cell parameters from 4598 reflections
b = 11.4765 (2) Å	θ = 2.4–29.1°
c = 11.9091 (2) Å	µ = 0.20 mm⁻¹
α = 75.206 (1)°	T = 296 K
β = 72.553 (1)°	Block, yellow
γ = 69.416 (1)°	0.33 × 0.25 × 0.13 mm
V = 1020.02 (3) Å³

Data collection top

Bruker APEXII CCD diffractometer	4451 independent reflections
Radiation source: fine-focus sealed tube	3628 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.016
ϕ and ω scans	θ_max = 27.0°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→10
T_min = 0.938, T_max = 0.975	k = −14→14
9421 measured reflections	l = −15→15

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.121	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ²(F_o²) + (0.0692P)² + 0.1602P] where P = (F_o² + 2F_c²)/3
4451 reflections	(Δ/σ)_max = 0.001
338 parameters	Δρ_max = 0.20 e Å⁻³
30 restraints	Δρ_min = −0.28 e Å⁻³

Crystal data top

C₁₇H₁₂N₆O₂S·C₄H₈O	γ = 69.416 (1)°
M_r = 436.49	V = 1020.02 (3) Å³
Triclinic, P1	Z = 2
a = 8.4768 (1) Å	Mo Kα radiation
b = 11.4765 (2) Å	µ = 0.20 mm⁻¹
c = 11.9091 (2) Å	T = 296 K
α = 75.206 (1)°	0.33 × 0.25 × 0.13 mm
β = 72.553 (1)°

Data collection top

Bruker APEXII CCD diffractometer	4451 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3628 reflections with I > 2σ(I)
T_min = 0.938, T_max = 0.975	R_int = 0.016
9421 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	30 restraints
wR(F²) = 0.121	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	Δρ_max = 0.20 e Å⁻³
4451 reflections	Δρ_min = −0.28 e Å⁻³
338 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	Occ. (<1)
S1	0.05012 (6)	0.21013 (4)	0.21038 (4)	0.05637 (15)
O1	0.25587 (17)	−0.15327 (11)	0.48629 (10)	0.0564 (3)
O2	0.20530 (16)	0.44464 (11)	0.49172 (9)	0.0529 (3)
N1	0.38131 (19)	−0.19240 (13)	0.64563 (12)	0.0498 (3)
H1	0.402 (2)	−0.2746 (14)	0.6651 (16)	0.060*
N2	0.21787 (17)	0.11827 (12)	0.49897 (11)	0.0435 (3)
N3	0.16236 (18)	0.11149 (12)	0.40644 (12)	0.0455 (3)
H3	0.163 (2)	0.0406 (14)	0.3970 (16)	0.055*
N4	0.13631 (18)	0.32009 (11)	0.34784 (11)	0.0437 (3)
H4	0.167 (2)	0.3167 (17)	0.4115 (13)	0.052*
N5	0.11499 (16)	0.42919 (11)	0.26740 (11)	0.0411 (3)
N6	0.18651 (18)	0.64925 (12)	0.39333 (11)	0.0470 (3)
H6	0.217 (2)	0.6750 (18)	0.4406 (15)	0.056*
C1	0.3000 (2)	−0.11911 (14)	0.55902 (13)	0.0448 (3)
C2	0.2764 (2)	0.01502 (14)	0.56776 (13)	0.0417 (3)
C3	0.3419 (2)	0.00786 (15)	0.66947 (13)	0.0442 (3)
C4	0.3523 (3)	0.09899 (18)	0.72112 (17)	0.0617 (5)
H4A	0.3114	0.1843	0.6909	0.074*
C5	0.4251 (3)	0.0596 (2)	0.81909 (18)	0.0709 (5)
H5	0.4332	0.1193	0.8555	0.085*
C6	0.4860 (3)	−0.0675 (2)	0.86359 (16)	0.0634 (5)
H6A	0.5342	−0.0916	0.9297	0.076*
C7	0.4769 (2)	−0.15979 (17)	0.81209 (14)	0.0542 (4)
H7	0.5184	−0.2451	0.8421	0.065*
C8	0.4042 (2)	−0.11990 (15)	0.71482 (13)	0.0441 (3)
C9	0.1173 (2)	0.21704 (14)	0.32405 (13)	0.0423 (3)
C10	0.1806 (2)	0.52963 (14)	0.40708 (13)	0.0425 (3)
C11	0.13649 (18)	0.52272 (13)	0.29545 (12)	0.0388 (3)
C12	0.12560 (19)	0.64527 (13)	0.21980 (13)	0.0399 (3)
C13	0.0978 (2)	0.69308 (15)	0.10567 (13)	0.0469 (4)
H13	0.0746	0.6448	0.0641	0.056*
C14	0.1054 (2)	0.81390 (16)	0.05535 (15)	0.0558 (4)
H14	0.0881	0.8473	−0.0213	0.067*
C15	0.1386 (3)	0.88613 (16)	0.11776 (17)	0.0600 (5)
H15	0.1432	0.9674	0.0820	0.072*
C16	0.1649 (2)	0.84010 (15)	0.23188 (16)	0.0544 (4)
H16	0.1860	0.8891	0.2737	0.065*
C17	0.1587 (2)	0.71911 (14)	0.28141 (13)	0.0426 (3)
O3	0.446 (3)	0.5472 (16)	0.7408 (9)	0.054 (3)	0.561 (11)
C18	0.3597 (15)	0.4754 (11)	0.7110 (8)	0.073 (3)	0.561 (11)
H18C	0.4432	0.4071	0.6710	0.087*	0.561 (11)
H18D	0.2833	0.5288	0.6592	0.087*	0.561 (11)
C19	0.2583 (7)	0.4248 (5)	0.8281 (7)	0.0748 (19)	0.561 (11)
H19C	0.2449	0.3451	0.8256	0.090*	0.561 (11)
H19D	0.1447	0.4843	0.8505	0.090*	0.561 (11)
C20	0.3706 (7)	0.4076 (5)	0.9136 (5)	0.0656 (13)	0.561 (11)
H20C	0.3065	0.4015	0.9963	0.079*	0.561 (11)
H20D	0.4731	0.3351	0.9042	0.079*	0.561 (11)
C21	0.4135 (17)	0.5314 (11)	0.8674 (8)	0.062 (2)	0.561 (11)
H21C	0.3172	0.6007	0.8976	0.075*	0.561 (11)
H21D	0.5151	0.5278	0.8914	0.075*	0.561 (11)
O3'	0.471 (3)	0.545 (2)	0.7353 (11)	0.049 (2)	0.439 (11)
C18'	0.3702 (17)	0.5049 (11)	0.6829 (10)	0.058 (2)	0.439 (11)
H18A	0.4341	0.4837	0.6047	0.070*	0.439 (11)
H18B	0.2623	0.5705	0.6754	0.070*	0.439 (11)
C19'	0.3368 (12)	0.3903 (7)	0.7693 (8)	0.078 (2)	0.439 (11)
H19A	0.4385	0.3170	0.7618	0.094*	0.439 (11)
H19B	0.2398	0.3711	0.7591	0.094*	0.439 (11)
C20'	0.2948 (18)	0.4357 (11)	0.8886 (8)	0.109 (4)	0.439 (11)
H20A	0.1763	0.4895	0.9079	0.131*	0.439 (11)
H20B	0.3140	0.3652	0.9535	0.131*	0.439 (11)
C21'	0.4234 (19)	0.5088 (14)	0.8621 (11)	0.062 (3)	0.439 (11)
H21A	0.3714	0.5832	0.9000	0.074*	0.439 (11)
H21B	0.5249	0.4567	0.8922	0.074*	0.439 (11)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0781 (3)	0.0465 (2)	0.0592 (3)	−0.0176 (2)	−0.0398 (2)	−0.00685 (18)
O1	0.0811 (8)	0.0489 (6)	0.0550 (7)	−0.0291 (6)	−0.0329 (6)	−0.0013 (5)
O2	0.0720 (8)	0.0532 (6)	0.0403 (6)	−0.0235 (6)	−0.0238 (5)	0.0002 (5)
N1	0.0666 (9)	0.0398 (7)	0.0513 (8)	−0.0214 (6)	−0.0276 (7)	0.0027 (6)
N2	0.0528 (7)	0.0407 (6)	0.0406 (6)	−0.0147 (5)	−0.0171 (5)	−0.0045 (5)
N3	0.0621 (8)	0.0359 (6)	0.0462 (7)	−0.0167 (6)	−0.0251 (6)	−0.0024 (5)
N4	0.0616 (8)	0.0368 (6)	0.0390 (6)	−0.0157 (6)	−0.0221 (6)	−0.0031 (5)
N5	0.0518 (7)	0.0361 (6)	0.0380 (6)	−0.0123 (5)	−0.0171 (5)	−0.0041 (5)
N6	0.0634 (8)	0.0460 (7)	0.0417 (7)	−0.0197 (6)	−0.0196 (6)	−0.0108 (5)
C1	0.0539 (9)	0.0416 (8)	0.0438 (8)	−0.0205 (7)	−0.0171 (7)	0.0002 (6)
C2	0.0484 (8)	0.0412 (7)	0.0386 (7)	−0.0162 (6)	−0.0132 (6)	−0.0042 (6)
C3	0.0511 (8)	0.0457 (8)	0.0376 (7)	−0.0151 (6)	−0.0140 (6)	−0.0046 (6)
C4	0.0863 (13)	0.0511 (9)	0.0559 (10)	−0.0162 (9)	−0.0307 (9)	−0.0118 (8)
C5	0.1002 (16)	0.0693 (12)	0.0592 (11)	−0.0239 (11)	−0.0358 (11)	−0.0190 (9)
C6	0.0763 (12)	0.0757 (12)	0.0461 (9)	−0.0234 (10)	−0.0281 (9)	−0.0061 (8)
C7	0.0612 (10)	0.0577 (10)	0.0451 (8)	−0.0196 (8)	−0.0212 (7)	0.0023 (7)
C8	0.0474 (8)	0.0483 (8)	0.0396 (7)	−0.0197 (7)	−0.0124 (6)	−0.0017 (6)
C9	0.0478 (8)	0.0392 (7)	0.0431 (8)	−0.0128 (6)	−0.0159 (6)	−0.0062 (6)
C10	0.0492 (8)	0.0453 (8)	0.0374 (7)	−0.0155 (6)	−0.0140 (6)	−0.0080 (6)
C11	0.0450 (8)	0.0382 (7)	0.0350 (7)	−0.0121 (6)	−0.0124 (6)	−0.0063 (5)
C12	0.0451 (8)	0.0370 (7)	0.0387 (7)	−0.0116 (6)	−0.0115 (6)	−0.0069 (6)
C13	0.0564 (9)	0.0452 (8)	0.0407 (8)	−0.0138 (7)	−0.0158 (7)	−0.0065 (6)
C14	0.0693 (11)	0.0483 (9)	0.0450 (8)	−0.0145 (8)	−0.0188 (8)	0.0026 (7)
C15	0.0777 (12)	0.0387 (8)	0.0625 (10)	−0.0189 (8)	−0.0206 (9)	0.0008 (7)
C16	0.0696 (11)	0.0410 (8)	0.0587 (10)	−0.0185 (7)	−0.0184 (8)	−0.0118 (7)
C17	0.0483 (8)	0.0388 (7)	0.0423 (8)	−0.0110 (6)	−0.0130 (6)	−0.0092 (6)
O3	0.066 (6)	0.049 (3)	0.053 (3)	−0.023 (4)	−0.019 (2)	−0.003 (2)
C18	0.085 (4)	0.078 (7)	0.080 (4)	−0.035 (4)	−0.037 (3)	−0.019 (4)
C19	0.059 (3)	0.053 (2)	0.115 (5)	−0.020 (2)	−0.028 (3)	−0.005 (3)
C20	0.070 (3)	0.053 (2)	0.073 (3)	−0.0203 (19)	−0.032 (2)	0.0115 (18)
C21	0.098 (6)	0.048 (3)	0.041 (3)	−0.029 (4)	−0.004 (3)	−0.012 (2)
O3'	0.055 (5)	0.054 (4)	0.047 (4)	−0.015 (2)	−0.021 (3)	−0.014 (3)
C18'	0.057 (4)	0.047 (4)	0.080 (5)	−0.012 (3)	−0.029 (4)	−0.016 (4)
C19'	0.072 (4)	0.057 (3)	0.112 (5)	−0.028 (3)	−0.014 (4)	−0.022 (3)
C20'	0.152 (11)	0.123 (8)	0.079 (5)	−0.090 (8)	−0.025 (6)	0.009 (5)
C21'	0.066 (5)	0.059 (6)	0.059 (5)	−0.005 (3)	−0.016 (3)	−0.023 (3)

Geometric parameters (Å, º) top

S1—C9	1.6467 (15)	C13—H13	0.9300
O1—C1	1.2307 (18)	C14—C15	1.387 (3)
O2—C10	1.2215 (18)	C14—H14	0.9300
N1—C1	1.350 (2)	C15—C16	1.381 (3)
N1—C8	1.403 (2)	C15—H15	0.9300
N1—H1	0.877 (14)	C16—C17	1.376 (2)
N2—C2	1.2868 (19)	C16—H16	0.9300
N2—N3	1.3498 (17)	O3—C21	1.424 (9)
N3—C9	1.3670 (19)	O3—C18	1.438 (9)
N3—H3	0.847 (14)	C18—C19	1.496 (9)
N4—C9	1.3557 (19)	C18—H18C	0.9700
N4—N5	1.3601 (17)	C18—H18D	0.9700
N4—H4	0.860 (14)	C19—C20	1.527 (6)
N5—C11	1.2861 (18)	C19—H19C	0.9700
N6—C10	1.357 (2)	C19—H19D	0.9700
N6—C17	1.4088 (19)	C20—C21	1.516 (9)
N6—H6	0.837 (14)	C20—H20C	0.9700
C1—C2	1.508 (2)	C20—H20D	0.9700
C2—C3	1.450 (2)	C21—H21C	0.9700
C3—C4	1.380 (2)	C21—H21D	0.9700
C3—C8	1.394 (2)	O3'—C21'	1.430 (11)
C4—C5	1.383 (3)	O3'—C18'	1.438 (11)
C4—H4A	0.9300	C18'—C19'	1.504 (9)
C5—C6	1.384 (3)	C18'—H18A	0.9700
C5—H5	0.9300	C18'—H18B	0.9700
C6—C7	1.386 (3)	C19'—C20'	1.536 (10)
C6—H6A	0.9300	C19'—H19A	0.9700
C7—C8	1.375 (2)	C19'—H19B	0.9700
C7—H7	0.9300	C20'—C21'	1.515 (11)
C10—C11	1.5123 (19)	C20'—H20A	0.9700
C11—C12	1.4525 (19)	C20'—H20B	0.9700
C12—C13	1.387 (2)	C21'—H21A	0.9700
C12—C17	1.394 (2)	C21'—H21B	0.9700
C13—C14	1.379 (2)

C1—N1—C8	111.71 (13)	C14—C15—H15	119.3
C1—N1—H1	124.8 (13)	C17—C16—C15	117.62 (15)
C8—N1—H1	122.7 (13)	C17—C16—H16	121.2
C2—N2—N3	118.31 (12)	C15—C16—H16	121.2
N2—N3—C9	119.91 (12)	C16—C17—C12	121.62 (14)
N2—N3—H3	119.6 (12)	C16—C17—N6	128.80 (14)
C9—N3—H3	120.3 (12)	C12—C17—N6	109.57 (12)
C9—N4—N5	119.78 (12)	C21—O3—C18	108.8 (8)
C9—N4—H4	121.0 (12)	O3—C18—C19	104.9 (7)
N5—N4—H4	119.1 (12)	O3—C18—H18C	110.8
C11—N5—N4	116.37 (12)	C19—C18—H18C	110.8
C10—N6—C17	111.43 (12)	O3—C18—H18D	110.8
C10—N6—H6	124.2 (13)	C19—C18—H18D	110.8
C17—N6—H6	123.8 (13)	H18C—C18—H18D	108.8
O1—C1—N1	127.78 (14)	C18—C19—C20	102.6 (5)
O1—C1—C2	126.52 (14)	C18—C19—H19C	111.3
N1—C1—C2	105.69 (12)	C20—C19—H19C	111.3
N2—C2—C3	124.33 (14)	C18—C19—H19D	111.3
N2—C2—C1	129.33 (13)	C20—C19—H19D	111.3
C3—C2—C1	106.29 (12)	H19C—C19—H19D	109.2
C4—C3—C8	120.65 (15)	C21—C20—C19	97.6 (5)
C4—C3—C2	132.58 (15)	C21—C20—H20C	112.2
C8—C3—C2	106.77 (13)	C19—C20—H20C	112.2
C3—C4—C5	118.04 (17)	C21—C20—H20D	112.2
C3—C4—H4A	121.0	C19—C20—H20D	112.2
C5—C4—H4A	121.0	H20C—C20—H20D	109.8
C4—C5—C6	120.79 (18)	O3—C21—C20	105.2 (8)
C4—C5—H5	119.6	O3—C21—H21C	110.7
C6—C5—H5	119.6	C20—C21—H21C	110.7
C5—C6—C7	121.64 (16)	O3—C21—H21D	110.7
C5—C6—H6A	119.2	C20—C21—H21D	110.7
C7—C6—H6A	119.2	H21C—C21—H21D	108.8
C8—C7—C6	117.22 (16)	C21'—O3'—C18'	108.2 (10)
C8—C7—H7	121.4	O3'—C18'—C19'	103.9 (9)
C6—C7—H7	121.4	O3'—C18'—H18A	111.0
C7—C8—C3	121.65 (15)	C19'—C18'—H18A	111.0
C7—C8—N1	128.92 (15)	O3'—C18'—H18B	111.0
C3—C8—N1	109.42 (13)	C19'—C18'—H18B	111.0
N4—C9—N3	112.67 (13)	H18A—C18'—H18B	109.0
N4—C9—S1	126.85 (11)	C18'—C19'—C20'	100.5 (7)
N3—C9—S1	120.48 (11)	C18'—C19'—H19A	111.7
O2—C10—N6	127.57 (14)	C20'—C19'—H19A	111.7
O2—C10—C11	126.71 (13)	C18'—C19'—H19B	111.7
N6—C10—C11	105.72 (12)	C20'—C19'—H19B	111.7
N5—C11—C12	124.64 (13)	H19A—C19'—H19B	109.4
N5—C11—C10	129.04 (13)	C21'—C20'—C19'	101.2 (8)
C12—C11—C10	106.31 (12)	C21'—C20'—H20A	111.5
C13—C12—C17	120.17 (13)	C19'—C20'—H20A	111.5
C13—C12—C11	132.86 (13)	C21'—C20'—H20B	111.5
C17—C12—C11	106.91 (12)	C19'—C20'—H20B	111.5
C14—C13—C12	118.37 (15)	H20A—C20'—H20B	109.3
C14—C13—H13	120.8	O3'—C21'—C20'	107.5 (9)
C12—C13—H13	120.8	O3'—C21'—H21A	110.2
C13—C14—C15	120.77 (15)	C20'—C21'—H21A	110.2
C13—C14—H14	119.6	O3'—C21'—H21B	110.2
C15—C14—H14	119.6	C20'—C21'—H21B	110.2
C16—C15—C14	121.45 (15)	H21A—C21'—H21B	108.5
C16—C15—H15	119.3

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O3ⁱ	0.88 (1)	1.96 (2)	2.829 (15)	168 (2)
N1—H1···O3′ⁱ	0.88 (1)	1.98 (3)	2.84 (2)	167 (2)
N3—H3···O1	0.85 (1)	2.18 (2)	2.8369 (16)	134 (2)
N4—H4···O2	0.86 (1)	2.10 (2)	2.7857 (16)	136 (2)
N6—H6···O1ⁱⁱ	0.84 (1)	2.32 (2)	3.0522 (16)	146 (2)

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

Experimental details

Crystal data
Chemical formula	C₁₇H₁₂N₆O₂S·C₄H₈O
M_r	436.49
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	8.4768 (1), 11.4765 (2), 11.9091 (2)
α, β, γ (°)	75.206 (1), 72.553 (1), 69.416 (1)
V (Å³)	1020.02 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.20
Crystal size (mm)	0.33 × 0.25 × 0.13

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.938, 0.975
No. of measured, independent and observed [I > 2σ(I)] reflections	9421, 4451, 3628
R_int	0.016
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.121, 1.05
No. of reflections	4451
No. of parameters	338
No. of restraints	30
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.20, −0.28

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SAINT (Bruker, 2007, SHELXS97 (Sheldrick, 2008), X-SEED (Barbour, 2001), SHELXL97 (Sheldrick, 2008) and publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O3ⁱ	0.877 (14)	1.96 (2)	2.829 (15)	168.3 (18)
N1—H1···O3'ⁱ	0.877 (14)	1.98 (3)	2.84 (2)	167.4 (18)
N3—H3···O1	0.847 (14)	2.183 (16)	2.8369 (16)	133.9 (16)
N4—H4···O2	0.860 (14)	2.101 (16)	2.7857 (16)	136.2 (16)
N6—H6···O1ⁱⁱ	0.837 (14)	2.322 (16)	3.0522 (16)	146.0 (17)

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

Acknowledgements

We thank the University of Malaya for funding this study (ERGS grant No. ER009–2011 A).

References

Bacchi, A., Carcelli, M., Pelagatti, P., Pelizzi, G., Rodriguez-Arguelles, M. C., Rogolino, D., Solinas, C. & Zani, F. (2005). J. Inorg. Biochem. 99, 397–408. Web of Science CSD CrossRef PubMed CAS Google Scholar
Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 6| June 2012| Page o1870

doi:10.1107/S1600536812022714

Open

access

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

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

1,5-Bis(2-oxoindolin-3-yl­­idene)thio­carbonohydrazide tetra­hydro­furan monosolvate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

1,5-Bis(2-oxoindolin-3-ylidene)thiocarbonohydrazide tetrahydrofuran monosolvate