1-(5-Nitro-2-oxoindolin-3-yl-idene)-4-o-tolyl-thio-semicarbazide methanol monosolvate.

In the title compound, C(16)H(13)N(5)O(3)S·CH(4)O, the dihedral angle between the isatin unit and the 2-methyl-phenyl group is 41.81 (2)° and intra-molecular N-H⋯O and N-H⋯N hydrogen bonds occur, generating S(6) and S(5) rings, respectively. In the crystal, polymeric chains arise as a result of N-H⋯O, O-H⋯S and C-H⋯O inter-actions.

Related literature

For related structures, see: Revenko et al. (1994 ▶); Pervez et al. (2009 ▶). For graph-set theory, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C16H13N5O3S·CH4O

M = 387.42

Monoclinic,

a = 14.2485 (5) Å

b = 7.6986 (3) Å

c = 18.5937 (6) Å

β = 119.847 (2)°

V = 1769.07 (11) Å3

Z = 4

Mo Kα radiation

μ = 0.22 mm−1

T = 296 K

0.30 × 0.16 × 0.12 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.963, T max = 0.974

18543 measured reflections

4005 independent reflections

2975 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.098

S = 1.03

4005 reflections

249 parameters

H-atom parameters constrained

Δρmax = 0.24 e Å−3

Δρmin = −0.22 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: ORTEP-3 for Windows (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809043633/hb5167sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809043633/hb5167Isup2.hkl

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

C16H13N5O3S·CH4O	F(000) = 808
Mr = 387.42	Dx = 1.455 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2975 reflections
a = 14.2485 (5) Å	θ = 2.5–27.5°
b = 7.6986 (3) Å	µ = 0.22 mm−1
c = 18.5937 (6) Å	T = 296 K
β = 119.847 (2)°	Cut needle, yellow
V = 1769.07 (11) Å3	0.30 × 0.16 × 0.12 mm
Z = 4

Bruker Kappa APEXII CCD diffractometer	4005 independent reflections
Radiation source: fine-focus sealed tube	2975 reflections with I > 2σ(I)
graphite	Rint = 0.031
Detector resolution: 7.60 pixels mm-1	θmax = 27.5°, θmin = 2.5°
ω scans	h = −18→18
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −10→10
Tmin = 0.963, Tmax = 0.974	l = −23→23
18543 measured reflections

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.098	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0413P)2 + 0.4905P] where P = (Fo2 + 2Fc2)/3
4005 reflections	(Δ/σ)max < 0.001
249 parameters	Δρmax = 0.24 e Å−3
0 restraints	Δρmin = −0.22 e Å−3

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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
S1	0.36128 (4)	−0.18526 (6)	0.42815 (3)	0.0480 (2)
O1	0.43184 (10)	0.09444 (15)	0.66176 (7)	0.0471 (4)
O2	0.09516 (11)	0.88792 (17)	0.44105 (8)	0.0535 (5)
O3	0.14063 (12)	1.04229 (17)	0.54995 (9)	0.0631 (5)
N1	0.39348 (11)	0.35294 (18)	0.70502 (8)	0.0388 (4)
N2	0.28711 (10)	0.24879 (17)	0.49325 (8)	0.0342 (4)
N3	0.33161 (11)	0.09298 (17)	0.49406 (8)	0.0390 (4)
N4	0.20990 (10)	0.06337 (17)	0.35699 (8)	0.0364 (4)
N5	0.14422 (11)	0.90750 (18)	0.51621 (9)	0.0408 (5)
C1	0.28486 (11)	0.4853 (2)	0.58087 (9)	0.0309 (4)
C2	0.22200 (12)	0.6183 (2)	0.52973 (10)	0.0329 (5)
C3	0.21086 (12)	0.7648 (2)	0.56800 (10)	0.0342 (5)
C4	0.25938 (13)	0.7812 (2)	0.65330 (10)	0.0380 (5)
C5	0.32173 (13)	0.6488 (2)	0.70422 (10)	0.0385 (5)
C6	0.33402 (12)	0.5016 (2)	0.66721 (9)	0.0330 (4)
C7	0.38889 (12)	0.2370 (2)	0.64829 (10)	0.0362 (5)
C8	0.31690 (12)	0.3173 (2)	0.56487 (9)	0.0314 (4)
C9	0.29577 (12)	−0.0024 (2)	0.42330 (9)	0.0346 (5)
C10	0.14634 (12)	−0.0135 (2)	0.27704 (9)	0.0330 (5)
C11	0.11584 (12)	0.0923 (2)	0.20843 (10)	0.0367 (5)
C12	0.04962 (14)	0.0193 (3)	0.13070 (10)	0.0470 (6)
C13	0.01474 (14)	−0.1498 (3)	0.12170 (11)	0.0501 (6)
C14	0.04524 (13)	−0.2512 (2)	0.19058 (12)	0.0466 (6)
C15	0.11076 (14)	−0.1830 (2)	0.26893 (11)	0.0413 (5)
C16	0.15262 (16)	0.2771 (3)	0.21779 (12)	0.0543 (6)
O4	0.46564 (14)	0.2556 (2)	0.37038 (8)	0.0764 (6)
C17	0.43827 (17)	0.4240 (3)	0.37829 (13)	0.0599 (7)
H1	0.42879	0.33638	0.75775	0.0465*
H2	0.18875	0.60978	0.47231	0.0395*
H3	0.38341	0.05337	0.53999	0.0468*
H4	0.24971	0.88234	0.67621	0.0456*
H4A	0.19014	0.16531	0.36307	0.0437*
H5	0.35450	0.65800	0.76159	0.0462*
H12	0.02844	0.08685	0.08361	0.0563*
H13	−0.02945	−0.19550	0.06905	0.0601*
H14	0.02187	−0.36585	0.18459	0.0559*
H15	0.13064	−0.25081	0.31575	0.0496*
H16A	0.23026	0.28089	0.24674	0.0814*
H16B	0.12630	0.34033	0.24866	0.0814*
H16C	0.12490	0.32864	0.16396	0.0814*
H4B	0.50868	0.21697	0.41631	0.0916*
H17A	0.38390	0.42215	0.39442	0.0898*
H17B	0.41066	0.48319	0.32618	0.0898*
H17C	0.50125	0.48363	0.41975	0.0898*

	U11	U22	U33	U12	U13	U23
S1	0.0570 (3)	0.0429 (3)	0.0355 (3)	0.0174 (2)	0.0165 (2)	−0.0014 (2)
O1	0.0506 (7)	0.0385 (7)	0.0345 (7)	0.0088 (5)	0.0077 (5)	0.0026 (5)
O2	0.0627 (8)	0.0480 (8)	0.0382 (8)	0.0117 (6)	0.0164 (6)	0.0063 (6)
O3	0.0910 (10)	0.0387 (8)	0.0612 (9)	0.0172 (7)	0.0390 (8)	−0.0016 (7)
N1	0.0443 (7)	0.0392 (8)	0.0220 (7)	−0.0009 (6)	0.0083 (6)	−0.0004 (6)
N2	0.0372 (7)	0.0302 (7)	0.0291 (7)	0.0014 (5)	0.0119 (6)	−0.0027 (6)
N3	0.0428 (7)	0.0361 (8)	0.0265 (7)	0.0084 (6)	0.0084 (6)	−0.0021 (6)
N4	0.0441 (7)	0.0288 (7)	0.0285 (7)	0.0046 (6)	0.0121 (6)	−0.0030 (6)
N5	0.0475 (8)	0.0347 (8)	0.0436 (9)	0.0026 (6)	0.0253 (7)	0.0013 (7)
C1	0.0333 (7)	0.0308 (8)	0.0254 (8)	−0.0043 (6)	0.0122 (6)	−0.0032 (6)
C2	0.0359 (8)	0.0346 (8)	0.0251 (8)	−0.0021 (6)	0.0129 (6)	−0.0012 (7)
C3	0.0361 (8)	0.0322 (8)	0.0341 (9)	−0.0005 (6)	0.0174 (7)	0.0012 (7)
C4	0.0428 (8)	0.0359 (9)	0.0364 (9)	−0.0039 (7)	0.0205 (7)	−0.0094 (7)
C5	0.0430 (9)	0.0437 (10)	0.0258 (8)	−0.0063 (7)	0.0149 (7)	−0.0077 (7)
C6	0.0346 (7)	0.0333 (8)	0.0269 (8)	−0.0052 (6)	0.0122 (6)	−0.0016 (7)
C7	0.0355 (8)	0.0348 (9)	0.0285 (8)	−0.0031 (7)	0.0085 (6)	−0.0006 (7)
C8	0.0325 (7)	0.0305 (8)	0.0254 (8)	−0.0024 (6)	0.0100 (6)	−0.0006 (7)
C9	0.0397 (8)	0.0339 (9)	0.0288 (8)	0.0004 (7)	0.0159 (7)	−0.0005 (7)
C10	0.0339 (7)	0.0347 (9)	0.0278 (8)	0.0030 (6)	0.0134 (6)	−0.0027 (7)
C11	0.0347 (8)	0.0391 (9)	0.0333 (9)	0.0045 (7)	0.0146 (7)	0.0024 (7)
C12	0.0433 (9)	0.0588 (12)	0.0279 (9)	0.0085 (8)	0.0095 (7)	0.0049 (8)
C13	0.0396 (9)	0.0605 (12)	0.0356 (10)	0.0019 (8)	0.0077 (8)	−0.0153 (9)
C14	0.0428 (9)	0.0401 (10)	0.0518 (11)	−0.0056 (8)	0.0196 (8)	−0.0132 (9)
C15	0.0472 (9)	0.0368 (9)	0.0390 (10)	−0.0003 (7)	0.0207 (8)	0.0001 (8)
C16	0.0581 (11)	0.0461 (11)	0.0468 (11)	−0.0016 (9)	0.0171 (9)	0.0114 (9)
O4	0.1094 (13)	0.0594 (9)	0.0329 (8)	0.0304 (9)	0.0147 (8)	−0.0028 (7)
C17	0.0589 (11)	0.0478 (12)	0.0609 (14)	0.0006 (9)	0.0206 (10)	−0.0080 (10)

S1—C9	1.6666 (17)	C5—C6	1.381 (2)
O1—C7	1.220 (2)	C7—C8	1.502 (2)
O2—N5	1.2215 (19)	C10—C11	1.389 (2)
O3—N5	1.227 (2)	C10—C15	1.381 (2)
O4—C17	1.383 (3)	C11—C16	1.496 (3)
O4—H4B	0.8200	C11—C12	1.392 (2)
N1—C7	1.358 (2)	C12—C13	1.374 (3)
N1—C6	1.389 (2)	C13—C14	1.373 (3)
N2—N3	1.353 (2)	C14—C15	1.384 (3)
N2—C8	1.292 (2)	C2—H2	0.9300
N3—C9	1.365 (2)	C4—H4	0.9300
N4—C10	1.428 (2)	C5—H5	0.9300
N4—C9	1.331 (2)	C12—H12	0.9300
N5—C3	1.458 (2)	C13—H13	0.9300
N1—H1	0.8600	C14—H14	0.9300
N3—H3	0.8600	C15—H15	0.9300
N4—H4A	0.8600	C16—H16C	0.9600
C1—C2	1.381 (2)	C16—H16A	0.9600
C1—C8	1.451 (2)	C16—H16B	0.9600
C1—C6	1.402 (2)	C17—H17A	0.9600
C2—C3	1.384 (2)	C17—H17B	0.9600
C3—C4	1.385 (2)	C17—H17C	0.9600
C4—C5	1.374 (2)
C17—O4—H4B	109.00	N4—C10—C15	120.89 (14)
C6—N1—C7	111.53 (13)	N4—C10—C11	117.36 (14)
N3—N2—C8	116.02 (13)	C10—C11—C12	117.23 (16)
N2—N3—C9	121.18 (13)	C10—C11—C16	121.31 (15)
C9—N4—C10	128.37 (14)	C12—C11—C16	121.46 (16)
O2—N5—C3	118.45 (14)	C11—C12—C13	121.76 (17)
O3—N5—C3	118.61 (14)	C12—C13—C14	119.86 (17)
O2—N5—O3	122.94 (15)	C13—C14—C15	120.05 (16)
C6—N1—H1	124.00	C10—C15—C14	119.48 (15)
C7—N1—H1	124.00	C1—C2—H2	122.00
N2—N3—H3	119.00	C3—C2—H2	122.00
C9—N3—H3	119.00	C5—C4—H4	120.00
C10—N4—H4A	116.00	C3—C4—H4	120.00
C9—N4—H4A	116.00	C4—C5—H5	121.00
C2—C1—C6	120.36 (15)	C6—C5—H5	121.00
C2—C1—C8	133.02 (14)	C13—C12—H12	119.00
C6—C1—C8	106.61 (13)	C11—C12—H12	119.00
C1—C2—C3	116.82 (15)	C12—C13—H13	120.00
N5—C3—C4	118.52 (14)	C14—C13—H13	120.00
N5—C3—C2	118.56 (14)	C15—C14—H14	120.00
C2—C3—C4	122.92 (15)	C13—C14—H14	120.00
C3—C4—C5	120.31 (15)	C10—C15—H15	120.00
C4—C5—C6	117.66 (15)	C14—C15—H15	120.00
N1—C6—C1	109.71 (14)	C11—C16—H16B	109.00
N1—C6—C5	128.35 (14)	C11—C16—H16C	109.00
C1—C6—C5	121.94 (15)	C11—C16—H16A	109.00
N1—C7—C8	106.00 (13)	H16A—C16—H16C	109.00
O1—C7—C8	126.66 (15)	H16B—C16—H16C	109.00
O1—C7—N1	127.32 (15)	H16A—C16—H16B	109.00
N2—C8—C1	126.86 (14)	O4—C17—H17A	109.00
C1—C8—C7	106.14 (13)	O4—C17—H17B	109.00
N2—C8—C7	126.98 (15)	O4—C17—H17C	109.00
N3—C9—N4	114.76 (14)	H17A—C17—H17B	109.00
S1—C9—N4	127.11 (12)	H17A—C17—H17C	109.00
S1—C9—N3	118.14 (12)	H17B—C17—H17C	109.00
C11—C10—C15	121.60 (15)
C7—N1—C6—C1	1.2 (2)	C6—C1—C8—N2	178.05 (18)
C7—N1—C6—C5	−178.24 (19)	C6—C1—C8—C7	−0.3 (2)
C6—N1—C7—O1	−179.54 (19)	C1—C2—C3—N5	−179.37 (17)
C6—N1—C7—C8	−1.4 (2)	C1—C2—C3—C4	0.0 (3)
C8—N2—N3—C9	171.16 (17)	N5—C3—C4—C5	179.22 (18)
N3—N2—C8—C1	177.28 (17)	C2—C3—C4—C5	−0.2 (3)
N3—N2—C8—C7	−4.8 (3)	C3—C4—C5—C6	0.3 (3)
N2—N3—C9—S1	175.23 (13)	C4—C5—C6—N1	179.14 (19)
N2—N3—C9—N4	−5.1 (2)	C4—C5—C6—C1	−0.3 (3)
C10—N4—C9—S1	7.3 (3)	O1—C7—C8—N2	0.9 (3)
C10—N4—C9—N3	−172.36 (17)	O1—C7—C8—C1	179.19 (19)
C9—N4—C10—C11	−137.33 (19)	N1—C7—C8—N2	−177.33 (18)
C9—N4—C10—C15	47.0 (3)	N1—C7—C8—C1	1.0 (2)
O2—N5—C3—C2	4.6 (3)	N4—C10—C11—C12	−177.02 (18)
O2—N5—C3—C4	−174.76 (18)	N4—C10—C11—C16	2.9 (3)
O3—N5—C3—C2	−174.74 (18)	C15—C10—C11—C12	−1.4 (3)
O3—N5—C3—C4	5.9 (3)	C15—C10—C11—C16	178.6 (2)
C6—C1—C2—C3	0.0 (3)	N4—C10—C15—C14	177.10 (18)
C8—C1—C2—C3	−178.49 (19)	C11—C10—C15—C14	1.6 (3)
C2—C1—C6—N1	−179.38 (17)	C10—C11—C12—C13	0.6 (3)
C2—C1—C6—C5	0.1 (3)	C16—C11—C12—C13	−179.4 (2)
C8—C1—C6—N1	−0.5 (2)	C11—C12—C13—C14	0.0 (3)
C8—C1—C6—C5	178.98 (18)	C12—C13—C14—C15	0.2 (3)
C2—C1—C8—N2	−3.3 (3)	C13—C14—C15—C10	−1.0 (3)
C2—C1—C8—C7	178.38 (19)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···O1	0.86	2.04	2.7074 (17)	134
N4—H4A···N2	0.86	2.20	2.6254 (18)	110
N1—H1···O4i	0.86	2.02	2.8394 (19)	160
O4—H4B···S1ii	0.82	2.55	3.3485 (14)	164
C16—H16C···O3iii	0.96	2.45	3.342 (3)	154

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3⋯O1	0.86	2.04	2.7074 (17)	134
N4—H4A⋯N2	0.86	2.20	2.6254 (18)	110
N1—H1⋯O4i	0.86	2.02	2.8394 (19)	160
O4—H4B⋯S1ii	0.82	2.55	3.3485 (14)	164
C16—H16C⋯O3iii	0.96	2.45	3.342 (3)	154

Symmetry codes: (i) ; (ii) ; (iii) .