1,5-Bis(2-oxoindolin-3-yl-idene)thio-carbonohydrazide tetra-hydro-furan monosolvate.

In the thio-carbonohydrazide mol-ecule of the title compound, C(17)H(12)N(6)O(2)S·C(4)H(8)O, the terminal indolin-2-one ring systems make a dihedral angle of 20.13 (6)° with each other. Two intra-molecular 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 mol-ecular chain running along the b axis. The tetra-hydro-furan solvent mol-ecule 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 = 436.49

Triclinic,

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[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.121

S = 1.05

4451 reflections

338 parameters

30 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.20 e Å−3

Δρmin = −0.28 e Å−3

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 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812022714/is5142sup1.cif

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

Supplementary material file. DOI: 10.1107/S1600536812022714/is5142Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C17H12N6O2S·C4H8O	Z = 2
Mr = 436.49	F(000) = 456
Triclinic, P1	Dx = 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

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

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(Fo2) + (0.0692P)2 + 0.1602P] where P = (Fo2 + 2Fc2)/3
4451 reflections	(Δ/σ)max = 0.001
338 parameters	Δρmax = 0.20 e Å−3
30 restraints	Δρmin = −0.28 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	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)

	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)

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

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)

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) ; (ii) .