(Z)-4-Hexyl-1-(5-nitro-2-oxo-2,3-dihydro-1H-indol-3-yl­idene)thio­semicarbazide

Pervez, H.; Yaqub, M.; Manzoor, N.; Tahir, M.N.; Iqbal, M.S.

doi:10.1107/S1600536809040276

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 65| Part 11| November 2009| Pages o2698-o2699

https://doi.org/10.1107/S1600536809040276

Open

access

(Z)-4-Hexyl-1-(5-nitro-2-oxo-2,3-dihydro-1H-indol-3-ylidene)thiosemicarbazide

Humayun Pervez,^a Muhammad Yaqub,^a Nazia Manzoor,^a M. Nawaz Tahir ^b ^* and M. Saeed Iqbal ^c

^aDepartment of Chemistry, Bahauddin Zakariya University, Multan 60800, Pakistan, ^bDepartment of Physics, University of Sargodha, Sargodha, Pakistan, and ^cDepartment of Chemistry, Government College University, Lahore, Pakistan
^*Correspondence e-mail: dmntahir_uos@yahoo.com

(Received 26 September 2009; accepted 2 October 2009; online 10 October 2009)

In the title compound, C₁₅H₁₉N₅O₃S, intramolecular N—H⋯O, N—H⋯N and C—H⋯S interactions occur and the three terminal C atoms of the hexyl group are disordered over two sites with an occupancy ratio of 0.664 (12):0.336 (12). In the crystal, inversion dimers linked by pairs of N—H⋯O hydrogen bonds occur and C—H⋯O bonds link the dimers into chains. A short C=O⋯π contact is also present.

Related literature

For the syntheses and structures of isatin and isatin-derived thiosemicarbazones with biological and medicinal properties, see: Beauchard et al. (2006 ); Hyatt et al. (2007 ); Quenelle et al. (2006 ); Karali et al. (2007 ). For a related crystal structure, see: Bain et al. (1997 ). For the syntheses of potent urease inhibitors based on N(4)-arylsubstituted isatin-3-thiosemicarbazones, see: Pervez et al. (2008 , 2009 ). For the graph set analysis of hydrogen-bond patterns in crystal structures, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₁₅H₁₉N₅O₃S
M_r = 349.42
Monoclinic, P 2₁ /c
a = 11.9464 (6) Å
b = 4.8845 (3) Å
c = 29.9688 (17) Å
β = 101.131 (3)°
V = 1715.85 (17) Å³
Z = 4
Mo Kα radiation
μ = 0.21 mm⁻¹
T = 296 K
0.26 × 0.14 × 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
19438 measured reflections
4283 independent reflections
1964 reflections with I > 2σ(I)
R_int = 0.062

Refinement

R[F² > 2σ(F²)] = 0.054
wR(F²) = 0.143
S = 1.00
4283 reflections
247 parameters
6 restraints
H-atom parameters constrained
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O1ⁱ	0.86	2.08	2.871 (3)	153
N4—H4A⋯O1	0.86	2.02	2.721 (2)	138
N5—H5A⋯N3	0.86	2.32	2.688 (3)	106
C2—H2⋯O3ⁱⁱ	0.93	2.52	3.438 (3)	167
C10—H10B⋯O2ⁱⁱ	0.97	2.48	3.232 (4)	134
C7—O1⋯Cg1ⁱⁱⁱ	1.23 (1)	3.25 (1)	3.896 (3)	113 (1)
Symmetry codes: (i) -x+2, -y-1, -z; (ii) -x+1, -y+1, -z; (iii) -x+2, -y, -z. Cg1 is the centroid of the N2/C6/C1/C8/C7 ring.

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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536809040276/si2206sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536809040276/si2206Isup2.hkl

checkCIF report

Comment top

Isatin and its derivatives are known to possess a broad spectrum of pharmacological properties including antibacterial, anticonvulsant, antifungal, antineoplastic, antiviral, and enzymatic inhibition (Beauchard et al. 2006; Hyatt et al. 2007). Amongst these, isatins-derived thiosemicarbazones have gained a great deal of attention (Beauchard et al., 2006; Quenelle et al., 2006; Karali et al., 2007). Very recently, a number of N(4)-arylsubstituted isatin-3-thiosemicarbazones have been synthesized and reported as potent urease (a nickel-dependent metallo-enzyme) inhibitors (Pervez et al., 2008; Pervez et al., 2009). In continuation to the development of potent and non- or less toxic urease inhibitors, we report herein the crystal structure and preparation of the title compound (I, Fig. 1).

The crystal structure of (II) Indole-2,3-dione 3-(N(4)-ethylthiosemicarbazone) (N^'-2-(Thienylidene))benzhydrazide (Bain et al., 1997) has been published. The title compound (I) differs from (II) due to hexyl moiety instead of ethyl moiety.

The molecules of the title compound consist of dimers owing to N–H···O type of intermolecular H-bondings forming R₂²(8) ring motifs (Bernstein et al., 1995). The molecules are interlinked in the form of polymeric chains due to C—H···O type of intermolecular H-bondings (Table 1, Fig. 2). There exist two S(5) and a S(6), R₂²(10) and R₃³(12) or R₂²(13) ring motifs as well (Fig. 2). In the title compound the group (C1—C9/N1—N5/O—O3) of the isatin moiety along with nitro substitution is planar with maximum r.m.s. deviation of 0.0348 Å from the mean square plane and the sulphur atom S1 is at a distance of -0.3497 (16) Å from this mean square plane. The terminating three carbons of the hexyl group are disordered over two sites with occupancy ratio of 0.664 (12):0.336 (12). The C==O···π and N—O···π interactions (Table 1), may also be responsible for stabilizing of the molecules.

Related literature top

For the syntheses and structures of isatin and isatin-derived thiosemicarbazones with biological and medicinal properties, see: Beauchard et al. (2006); Hyatt et al. (2007); Quenelle et al. (2006); Karali et al. (2007). For a related crystal structure, see: Bain et al. (1997). For the syntheses of potent urease inhibitors based on N(4)-arylsubstituted isatin-3-thiosemicarbazones, see: Pervez et al. (2008, 2009). For the graph set analysis of hydrogen-bond patterns in crystal structures, see: Bernstein et al. (1995). Cg1 and Cg2 are the centroids of the N2/C6/C1/C8/C7 and C1–C6 rings, respectively.

Experimental top

A solution of N⁴-hexylthiosemicarbazide (0.44 g, 2.5 mmol) in ethanol (10 ml) was added to a hot solution of 5-nitroisatin (0.48 g, 2.5 mmol) in 50% aqueous ethanol (30 ml) containing a few drops of glacial acetic acid. The reaction mixture was then heated under reflux for 2 h. The yellow crystalline solid formed during heating was collected by suction filtration. Thorough washing with hot aqueous ethanol gave the title compound (I) in pure form (0.72 g, 82%), m.p. 513 K. The single crystals of (I) were grown in ethanol-n-hexane (1:4) system by diffusion method at room temperature.

Structure description top

For the syntheses and structures of isatin and isatin-derived thiosemicarbazones with biological and medicinal properties, see: Beauchard et al. (2006); Hyatt et al. (2007); Quenelle et al. (2006); Karali et al. (2007). For a related crystal structure, see: Bain et al. (1997). For the syntheses of potent urease inhibitors based on N(4)-arylsubstituted isatin-3-thiosemicarbazones, see: Pervez et al. (2008, 2009). For the graph set analysis of hydrogen-bond patterns in crystal structures, see: Bernstein et al. (1995). Cg1 and Cg2 are the centroids of the N2/C6/C1/C8/C7 and C1–C6 rings, respectively.

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

Figures top

	Fig. 1. View of (I) with the atom numbering scheme. The thermal ellipsoids are drawn at the 30% probability level. H-atoms are shown by small circles of arbitrary radii. The single dotted lines represent the intramolecular H-bondings and the atoms of low occupancy factor are joined by double dotted lines.
	Fig. 2. The partial packing (PLATON; Spek, 2009) which shows that the molecules form dimers which are joined in the form of polymeric chains.

(Z)-4-Hexyl-1-(5-nitro-2-oxo-2,3-dihydro-1H-indol-3- ylidene)thiosemicarbazide top

Crystal data top

C₁₅H₁₉N₅O₃S	F(000) = 736
M_r = 349.42	D_x = 1.353 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4283 reflections
a = 11.9464 (6) Å	θ = 2.8–28.3°
b = 4.8845 (3) Å	µ = 0.21 mm⁻¹
c = 29.9688 (17) Å	T = 296 K
β = 101.131 (3)°	Needle, yellow
V = 1715.85 (17) Å³	0.26 × 0.14 × 0.12 mm
Z = 4

Data collection top

Bruker Kappa APEXII CCD diffractometer	4283 independent reflections
Radiation source: fine-focus sealed tube	1964 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.062
Detector resolution: 7.40 pixels mm^-1	θ_max = 28.3°, θ_min = 2.8°
ω scans	h = −15→15
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −6→6
T_min = 0.963, T_max = 0.974	l = −39→39
19438 measured reflections

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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.143	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.0588P)²] where P = (F_o² + 2F_c²)/3
4283 reflections	(Δ/σ)_max = 0.001
247 parameters	Δρ_max = 0.18 e Å⁻³
6 restraints	Δρ_min = −0.21 e Å⁻³

Crystal data top

C₁₅H₁₉N₅O₃S	V = 1715.85 (17) Å³
M_r = 349.42	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 11.9464 (6) Å	µ = 0.21 mm⁻¹
b = 4.8845 (3) Å	T = 296 K
c = 29.9688 (17) Å	0.26 × 0.14 × 0.12 mm
β = 101.131 (3)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	4283 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	1964 reflections with I > 2σ(I)
T_min = 0.963, T_max = 0.974	R_int = 0.062
19438 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.054	6 restraints
wR(F²) = 0.143	H-atom parameters constrained
S = 1.00	Δρ_max = 0.18 e Å⁻³
4283 reflections	Δρ_min = −0.21 e Å⁻³
247 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
S1	1.08831 (6)	0.36613 (17)	0.14896 (3)	0.0774 (3)
O1	0.99569 (14)	−0.2388 (3)	0.03674 (5)	0.0529 (6)
O2	0.3667 (2)	0.1096 (6)	−0.11002 (9)	0.1287 (13)
O3	0.41037 (17)	0.3726 (5)	−0.05287 (8)	0.0877 (9)
N1	0.4324 (2)	0.1883 (6)	−0.07641 (10)	0.0709 (10)
N2	0.85164 (16)	−0.3241 (4)	−0.02531 (7)	0.0490 (7)
N3	0.83033 (16)	0.1924 (4)	0.05490 (7)	0.0458 (7)
N4	0.93056 (16)	0.1876 (4)	0.08428 (7)	0.0510 (8)
N5	0.87198 (16)	0.5295 (4)	0.12710 (6)	0.0503 (7)
C1	0.71964 (19)	−0.0082 (4)	−0.01440 (8)	0.0433 (8)
C2	0.6158 (2)	0.1275 (5)	−0.02523 (8)	0.0484 (8)
C3	0.5423 (2)	0.0476 (5)	−0.06399 (9)	0.0542 (9)
C4	0.5668 (2)	−0.1580 (5)	−0.09235 (9)	0.0605 (10)
C5	0.6693 (2)	−0.2938 (5)	−0.08188 (9)	0.0568 (10)
C6	0.7441 (2)	−0.2180 (4)	−0.04288 (8)	0.0459 (8)
C7	0.9006 (2)	−0.1945 (4)	0.01354 (8)	0.0448 (8)
C8	0.81712 (19)	0.0150 (4)	0.02204 (8)	0.0427 (8)
C9	0.9565 (2)	0.3694 (5)	0.11984 (9)	0.0496 (8)
C10	0.8834 (2)	0.7192 (5)	0.16504 (9)	0.0623 (10)
C11	0.8653 (3)	0.5848 (7)	0.20820 (10)	0.0824 (14)
C12	0.7498 (3)	0.4789 (8)	0.20746 (12)	0.0955 (17)
C13A	0.7475 (5)	0.3834 (17)	0.2565 (2)	0.077 (3)	0.664 (12)
C14A	0.6340 (6)	0.279 (2)	0.2605 (3)	0.102 (3)	0.664 (12)
C15A	0.6209 (16)	0.201 (4)	0.3075 (5)	0.127 (6)	0.664 (12)
C15B	0.635 (3)	0.256 (6)	0.3121 (11)	0.109 (10)	0.336 (12)
C13B	0.6968 (19)	0.273 (3)	0.2355 (6)	0.112 (7)	0.336 (12)
C14B	0.6793 (19)	0.418 (3)	0.2762 (4)	0.094 (6)	0.336 (12)
H2	0.59683	0.26707	−0.00692	0.0581*
H2A	0.88306	−0.45536	−0.03755	0.0587*
H4	0.51425	−0.20417	−0.11838	0.0726*
H4A	0.98036	0.06652	0.08074	0.0612*
H10B	0.82826	0.86578	0.15726	0.0747*
H11A	0.88335	0.71653	0.23276	0.0988*
H11B	0.91888	0.43442	0.21509	0.0988*
H12A	0.69345	0.62106	0.19818	0.1147*
H12B	0.73346	0.32686	0.18638	0.1147*
H13A	0.76759	0.53567	0.27726	0.0930*	0.664 (12)
H13B	0.80392	0.24041	0.26509	0.0930*	0.664 (12)
H14A	0.57765	0.41744	0.24905	0.1224*	0.664 (12)
H14B	0.61727	0.11930	0.24100	0.1224*	0.664 (12)
H15A	0.61520	0.36407	0.32492	0.1907*	0.664 (12)
H15B	0.55311	0.09342	0.30598	0.1907*	0.664 (12)
H15C	0.68605	0.09686	0.32190	0.1907*	0.664 (12)
H5	0.68764	−0.43231	−0.10052	0.0681*
H5A	0.80755	0.52050	0.10849	0.0603*
H10A	0.95894	0.79989	0.17013	0.0747*
H13C	0.74739	0.11816	0.24371	0.1345*	0.336 (12)
H13D	0.62469	0.20663	0.21835	0.1345*	0.336 (12)
H14C	0.75141	0.49973	0.29030	0.1130*	0.336 (12)
H14D	0.62625	0.56648	0.26657	0.1130*	0.336 (12)
H15D	0.67630	0.30834	0.34164	0.1633*	0.336 (12)
H15E	0.55557	0.29260	0.30999	0.1633*	0.336 (12)
H15F	0.64630	0.06410	0.30749	0.1633*	0.336 (12)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0496 (5)	0.0958 (6)	0.0813 (6)	0.0104 (4)	−0.0009 (4)	−0.0106 (4)
O1	0.0500 (11)	0.0514 (10)	0.0578 (11)	0.0164 (8)	0.0117 (9)	0.0052 (8)
O2	0.0754 (17)	0.194 (3)	0.1011 (19)	0.0471 (16)	−0.0218 (15)	−0.0188 (19)
O3	0.0657 (14)	0.0890 (15)	0.1102 (18)	0.0332 (11)	0.0215 (13)	0.0064 (13)
N1	0.0488 (15)	0.093 (2)	0.0701 (17)	0.0148 (14)	0.0096 (14)	0.0203 (15)
N2	0.0509 (13)	0.0428 (11)	0.0559 (13)	0.0130 (9)	0.0171 (10)	−0.0032 (10)
N3	0.0427 (12)	0.0470 (12)	0.0495 (12)	0.0089 (9)	0.0136 (10)	0.0063 (10)
N4	0.0472 (13)	0.0520 (13)	0.0538 (13)	0.0136 (9)	0.0097 (11)	−0.0028 (10)
N5	0.0474 (12)	0.0554 (12)	0.0465 (12)	0.0073 (10)	0.0054 (10)	−0.0050 (10)
C1	0.0450 (15)	0.0396 (12)	0.0485 (14)	0.0062 (11)	0.0170 (12)	0.0059 (11)
C2	0.0480 (15)	0.0466 (13)	0.0547 (16)	0.0125 (11)	0.0201 (13)	0.0062 (12)
C3	0.0433 (15)	0.0621 (17)	0.0588 (17)	0.0075 (12)	0.0136 (14)	0.0118 (14)
C4	0.0526 (17)	0.0727 (19)	0.0545 (17)	−0.0010 (14)	0.0062 (14)	0.0036 (14)
C5	0.0601 (18)	0.0592 (16)	0.0523 (16)	0.0038 (14)	0.0142 (14)	−0.0077 (13)
C6	0.0468 (15)	0.0418 (13)	0.0524 (15)	0.0066 (11)	0.0177 (12)	0.0059 (12)
C7	0.0469 (15)	0.0405 (13)	0.0498 (15)	0.0092 (11)	0.0167 (13)	0.0077 (12)
C8	0.0432 (14)	0.0400 (13)	0.0475 (14)	0.0092 (11)	0.0153 (12)	0.0049 (11)
C9	0.0478 (15)	0.0524 (14)	0.0497 (15)	0.0064 (12)	0.0122 (12)	0.0052 (12)
C10	0.0660 (18)	0.0582 (16)	0.0613 (18)	0.0066 (13)	0.0092 (14)	−0.0105 (14)
C11	0.100 (3)	0.091 (2)	0.057 (2)	0.0197 (19)	0.0171 (18)	−0.0106 (17)
C12	0.108 (3)	0.099 (3)	0.093 (3)	0.007 (2)	0.053 (2)	0.009 (2)
C13A	0.079 (4)	0.104 (5)	0.049 (4)	−0.012 (3)	0.012 (3)	−0.008 (3)
C14A	0.089 (5)	0.130 (7)	0.090 (6)	−0.017 (4)	0.023 (4)	0.023 (5)
C15A	0.113 (9)	0.188 (14)	0.078 (7)	−0.020 (7)	0.012 (6)	0.033 (8)
C15B	0.112 (18)	0.107 (12)	0.13 (2)	0.020 (12)	0.079 (16)	−0.002 (12)
C13B	0.142 (15)	0.096 (9)	0.115 (13)	−0.021 (9)	0.068 (12)	−0.024 (9)
C14B	0.123 (14)	0.089 (10)	0.081 (9)	−0.006 (8)	0.047 (10)	−0.012 (7)

Geometric parameters (Å, º) top

S1—C9	1.647 (3)	C13A—C14A	1.475 (10)
O1—C7	1.231 (3)	C13B—C14B	1.46 (2)
O2—N1	1.214 (4)	C14A—C15A	1.496 (18)
O3—N1	1.204 (4)	C14B—C15B	1.51 (4)
N1—C3	1.465 (4)	C2—H2	0.9300
N2—C6	1.391 (3)	C4—H4	0.9300
N2—C7	1.355 (3)	C5—H5	0.9300
N3—N4	1.343 (3)	C10—H10A	0.9700
N3—C8	1.298 (3)	C10—H10B	0.9700
N4—C9	1.376 (3)	C11—H11A	0.9700
N5—C9	1.328 (3)	C11—H11B	0.9700
N5—C10	1.453 (3)	C12—H12A	0.9700
N2—H2A	0.8600	C12—H12B	0.9700
N4—H4A	0.8600	C13A—H13A	0.9700
N5—H5A	0.8600	C13A—H13B	0.9700
C1—C2	1.389 (3)	C13B—H13D	0.9700
C1—C8	1.439 (3)	C13B—H13C	0.9700
C1—C6	1.400 (3)	C14A—H14B	0.9700
C2—C3	1.371 (4)	C14A—H14A	0.9700
C3—C4	1.383 (4)	C14B—H14C	0.9700
C4—C5	1.375 (3)	C14B—H14D	0.9700
C5—C6	1.378 (3)	C15A—H15B	0.9600
C7—C8	1.485 (3)	C15A—H15C	0.9600
C10—C11	1.503 (4)	C15A—H15A	0.9600
C11—C12	1.470 (5)	C15B—H15D	0.9600
C12—C13B	1.524 (18)	C15B—H15E	0.9600
C12—C13A	1.547 (7)	C15B—H15F	0.9600

S1···C11	3.636 (4)	C15A···H5^xii	3.0200
S1···H10A	2.7700	C15B···H5^xii	3.0200
S1···H11B	3.1100	H2···O3^vi	2.5200
S1···H13Aⁱ	3.0000	H2···O3	2.4400
S1···H15Cⁱⁱ	2.9000	H2A···O1^v	2.0800
S1···H14Cⁱ	2.9700	H2A···C7^v	3.0700
O1···N3	3.008 (3)	H4···O2	2.3900
O1···N4	2.721 (2)	H4A···O1	2.0200
O1···C9ⁱⁱⁱ	3.246 (3)	H4A···C7	2.4200
O1···C7^iv	3.001 (3)	H5···H15C^xiii	2.4600
O1···O1^iv	3.223 (2)	H5···C15B^xiii	3.0200
O1···N2^v	2.871 (3)	H5···C15A^xiii	3.0200
O1···C8^iv	3.289 (3)	H5···H15D^xiii	2.5100
O2···C10^vi	3.232 (4)	H5A···N3	2.3200
O3···C4^vii	3.317 (3)	H5A···O2^vi	2.7600
O3···C1^viii	3.295 (3)	H5A···O3^vi	2.8600
O1···H4A	2.0200	H10A···S1	2.7700
O1···H2A^v	2.0800	H10B···O2^vi	2.4800
O2···H10B^vi	2.4800	H10B···H12A	2.5100
O2···H12A^vi	2.9100	H11A···H13A	2.2800
O2···H5A^vi	2.7600	H11B···S1	3.1100
O2···H4	2.3900	H11B···H13B	2.4100
O3···H2	2.4400	H11B···C9	2.9900
O3···H2^vi	2.5200	H12A···H10B	2.5100
O3···H5A^vi	2.8600	H12A···H14D	2.3600
N2···O1^v	2.871 (3)	H12A···O2^vi	2.9100
N3···O1	3.008 (3)	H12A···H14A	2.4600
N3···N5	2.688 (3)	H12B···N5	2.8300
N3···C7^vii	3.408 (3)	H12B···H14B	2.5500
N4···O1	2.721 (2)	H13A···H11A	2.2800
N5···N3	2.688 (3)	H13A···S1ⁱⁱ	3.0000
N3···H5A	2.3200	H13B···H15C	2.5100
N5···H12B	2.8300	H13B···H11B	2.4100
C1···O3^viii	3.295 (3)	H13C···H15F	2.4600
C2···C5^vii	3.421 (3)	H14A···C14A^xi	3.0500
C4···O3ⁱⁱⁱ	3.317 (3)	H14A···C15A^xi	2.9800
C5···C2ⁱⁱⁱ	3.421 (3)	H14A···H15B^xi	2.2100
C7···N3ⁱⁱⁱ	3.408 (3)	H14A···H14B^xi	2.6000
C7···C7^iv	3.264 (3)	H14A···H12A	2.4600
C7···O1^iv	3.001 (3)	H14B···H12B	2.5500
C8···O1^iv	3.289 (3)	H14B···H14A^x	2.6000
C9···O1^vii	3.246 (3)	H14C···C11	3.0600
C10···O2^vi	3.232 (4)	H14C···S1ⁱⁱ	2.9700
C11···S1	3.636 (4)	H14D···H12A	2.3600
C4···H15D^ix	3.0900	H15A···C4^xiv	3.0200
C4···H15A^ix	3.0200	H15B···C14A^x	3.1000
C7···H2A^v	3.0700	H15B···H14A^x	2.2100
C7···H4A	2.4200	H15C···S1ⁱ	2.9000
C9···H11B	2.9900	H15C···H5^xii	2.4600
C11···H14C	3.0600	H15C···H13B	2.5100
C14A···H14A^x	3.0500	H15D···C4^xiv	3.0900
C14A···H15B^xi	3.1000	H15D···H5^xii	2.5100
C15A···H14A^x	2.9800	H15F···H13C	2.4600

O2—N1—O3	122.9 (3)	N5—C10—H10B	109.00
O2—N1—C3	117.8 (3)	C11—C10—H10A	109.00
O3—N1—C3	119.3 (3)	C11—C10—H10B	109.00
C6—N2—C7	111.42 (19)	H10A—C10—H10B	108.00
N4—N3—C8	116.6 (2)	C10—C11—H11A	108.00
N3—N4—C9	122.4 (2)	C10—C11—H11B	108.00
C9—N5—C10	123.0 (2)	C12—C11—H11A	108.00
C7—N2—H2A	124.00	C12—C11—H11B	108.00
C6—N2—H2A	124.00	H11A—C11—H11B	107.00
N3—N4—H4A	119.00	C11—C12—H12A	110.00
C9—N4—H4A	119.00	C11—C12—H12B	110.00
C10—N5—H5A	119.00	C13A—C12—H12A	110.00
C9—N5—H5A	119.00	C13A—C12—H12B	110.00
C2—C1—C6	119.3 (2)	H12A—C12—H12B	109.00
C6—C1—C8	106.66 (19)	C13B—C12—H12A	107.00
C2—C1—C8	134.1 (2)	C13B—C12—H12B	79.00
C1—C2—C3	117.4 (2)	C12—C13A—H13A	109.00
C2—C3—C4	123.4 (2)	C12—C13A—H13B	109.00
N1—C3—C4	118.0 (2)	C14A—C13A—H13A	109.00
N1—C3—C2	118.5 (2)	C14A—C13A—H13B	109.00
C3—C4—C5	119.7 (2)	H13A—C13A—H13B	108.00
C4—C5—C6	117.9 (2)	H13C—C13B—H13D	109.00
N2—C6—C1	109.2 (2)	C12—C13B—H13C	110.00
N2—C6—C5	128.4 (2)	C12—C13B—H13D	110.00
C1—C6—C5	122.4 (2)	C14B—C13B—H13C	110.00
O1—C7—C8	127.0 (2)	C14B—C13B—H13D	110.00
O1—C7—N2	127.0 (2)	C15A—C14A—H14A	109.00
N2—C7—C8	106.1 (2)	C15A—C14A—H14B	108.00
N3—C8—C1	126.2 (2)	C13A—C14A—H14B	108.00
N3—C8—C7	127.1 (2)	C13A—C14A—H14A	108.00
C1—C8—C7	106.71 (19)	H14A—C14A—H14B	107.00
N4—C9—N5	116.3 (2)	C13B—C14B—H14C	108.00
S1—C9—N5	126.8 (2)	C13B—C14B—H14D	108.00
S1—C9—N4	116.98 (18)	H14C—C14B—H14D	107.00
N5—C10—C11	112.8 (2)	C15B—C14B—H14D	108.00
C10—C11—C12	115.6 (3)	C15B—C14B—H14C	108.00
C11—C12—C13B	135.4 (8)	C14A—C15A—H15C	110.00
C11—C12—C13A	106.3 (3)	C14A—C15A—H15B	110.00
C12—C13A—C14A	111.5 (5)	H15B—C15A—H15C	110.00
C12—C13B—C14B	106.4 (11)	H15A—C15A—H15B	109.00
C13A—C14A—C15A	115.4 (9)	H15A—C15A—H15C	109.00
C13B—C14B—C15B	117.9 (17)	C14A—C15A—H15A	109.00
C1—C2—H2	121.00	C14B—C15B—H15D	109.00
C3—C2—H2	121.00	C14B—C15B—H15E	110.00
C3—C4—H4	120.00	C14B—C15B—H15F	109.00
C5—C4—H4	120.00	H15D—C15B—H15E	110.00
C4—C5—H5	121.00	H15D—C15B—H15F	109.00
C6—C5—H5	121.00	H15E—C15B—H15F	110.00
N5—C10—H10A	109.00

O2—N1—C3—C2	−177.7 (3)	C8—C1—C6—C5	−179.2 (2)
O2—N1—C3—C4	2.9 (4)	C2—C1—C8—N3	−2.5 (4)
O3—N1—C3—C2	1.3 (4)	C2—C1—C8—C7	179.8 (2)
O3—N1—C3—C4	−178.1 (3)	C6—C1—C8—N3	177.5 (2)
C7—N2—C6—C1	−0.2 (3)	C6—C1—C8—C7	−0.2 (2)
C7—N2—C6—C5	179.2 (2)	C1—C2—C3—N1	−179.6 (2)
C6—N2—C7—O1	−179.0 (2)	C1—C2—C3—C4	−0.2 (4)
C6—N2—C7—C8	0.1 (3)	N1—C3—C4—C5	179.7 (2)
C8—N3—N4—C9	178.2 (2)	C2—C3—C4—C5	0.3 (4)
N4—N3—C8—C1	−176.8 (2)	C3—C4—C5—C6	0.2 (4)
N4—N3—C8—C7	0.5 (3)	C4—C5—C6—N2	179.9 (2)
N3—N4—C9—S1	−172.11 (18)	C4—C5—C6—C1	−0.7 (4)
N3—N4—C9—N5	8.0 (3)	O1—C7—C8—N3	1.5 (4)
C10—N5—C9—S1	−4.1 (4)	O1—C7—C8—C1	179.2 (2)
C10—N5—C9—N4	175.8 (2)	N2—C7—C8—N3	−177.6 (2)
C9—N5—C10—C11	−83.5 (3)	N2—C7—C8—C1	0.1 (2)
C6—C1—C2—C3	−0.3 (3)	N5—C10—C11—C12	−65.1 (3)
C8—C1—C2—C3	179.7 (2)	C10—C11—C12—C13A	−173.3 (4)
C2—C1—C6—N2	−179.7 (2)	C11—C12—C13A—C14A	178.4 (6)
C2—C1—C6—C5	0.8 (3)	C12—C13A—C14A—C15A	−175.7 (10)
C8—C1—C6—N2	0.3 (2)

Symmetry codes: (i) −x+2, y−1/2, −z+1/2; (ii) −x+2, y+1/2, −z+1/2; (iii) x, y−1, z; (iv) −x+2, −y, −z; (v) −x+2, −y−1, −z; (vi) −x+1, −y+1, −z; (vii) x, y+1, z; (viii) −x+1, −y, −z; (ix) x, −y+1/2, z−1/2; (x) −x+1, y−1/2, −z+1/2; (xi) −x+1, y+1/2, −z+1/2; (xii) x, −y−1/2, z+1/2; (xiii) x, −y−1/2, z−1/2; (xiv) x, −y+1/2, z+1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O1^v	0.8600	2.0800	2.871 (3)	153.00
N4—H4A···O1	0.8600	2.0200	2.721 (2)	138.00
N5—H5A···N3	0.8600	2.3200	2.688 (3)	106.00
C2—H2···O3^vi	0.9300	2.5200	3.438 (3)	167.00
C10—H10A···S1	0.9700	2.7700	3.107 (3)	101.00
C10—H10B···O2^vi	0.9700	2.4800	3.232 (4)	134.00
C7—O1···Cg1^iv	1.23 (1)	3.25 (1)	3.896 (3)	113 (1)
N1—O3···Cg1^viii	1.20 (1)	3.65 (1)	4.201 (3)	109 (1)
N1—O3···Cg2^viii	1.20 (1)	3.65 (1)	4.192 (3)	109 (1)

Symmetry codes: (iv) −x+2, −y, −z; (v) −x+2, −y−1, −z; (vi) −x+1, −y+1, −z; (viii) −x+1, −y, −z.

Experimental details

Crystal data
Chemical formula	C₁₅H₁₉N₅O₃S
M_r	349.42
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	11.9464 (6), 4.8845 (3), 29.9688 (17)
β (°)	101.131 (3)
V (Å³)	1715.85 (17)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.21
Crystal size (mm)	0.26 × 0.14 × 0.12

Data collection
Diffractometer	Bruker Kappa APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.963, 0.974
No. of measured, independent and observed [I > 2σ(I)] reflections	19438, 4283, 1964
R_int	0.062
(sin θ/λ)_max (Å⁻¹)	0.667

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.054, 0.143, 1.00
No. of reflections	4283
No. of parameters	247
No. of restraints	6
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.18, −0.21

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009), WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O1ⁱ	0.8600	2.0800	2.871 (3)	153.00
N4—H4A···O1	0.8600	2.0200	2.721 (2)	138.00
N5—H5A···N3	0.8600	2.3200	2.688 (3)	106.00
C2—H2···O3ⁱⁱ	0.9300	2.5200	3.438 (3)	167.00
C10—H10A···S1	0.9700	2.7700	3.107 (3)	101.00
C10—H10B···O2ⁱⁱ	0.9700	2.4800	3.232 (4)	134.00
C7—O1···Cg1ⁱⁱⁱ	1.231 (3)	3.245 (2)	3.896 (3)	113.13 (13)
N1—O3···Cg1^iv	1.204 (4)	3.646 (2)	4.201 (3)	109.29 (18)
N1—O3···Cg2^iv	1.204 (4)	3.652 (3)	4.192 (3)	108.50 (19)

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

Acknowledgements

NM greatfully acknowledges the Higher Education Commission, Islamabad, Pakistan, for providing her with a Scholarship under the Indigenous PhD Program and also for partial funding of this research work.

References

Bain, G. A., West, D. X., Krejci, J., Valdés-Martínez, J., Hernández- Ortega, S. & Toscano, R. A. (1997). Polyhedron, 16, 855–862. CSD CrossRef CAS Web of Science Google Scholar
Beauchard, A., Ferandin, F. S., Lozach, O., Blairvacq, M., Meijer, L., Thiéry, V. & Besson. T. (2006). Bioorg. Med. Chem. 14, 6434–6443. Google Scholar
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573. CrossRef CAS Web of Science Google Scholar
Bruker (2005). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. CrossRef CAS IUCr Journals Google Scholar
Hyatt, J. L., Moak, T., Hatfield, M. J., Tsurkan, L., Edwards, C. C., Wierdl, M., Danks, M. K., Wadkins, R. M. & Potter, P. M. (2007). J. Med. Chem. 50, 1876–1885. Web of Science CrossRef PubMed CAS Google Scholar
Karali, N., Gürsoy, A., Kandemirli, F., Shvets, N., Kaynak, F. B., Özbey, S., Kovalishyn, V. & Dimoglo, A. (2007). Bioorg. Med. Chem. 15, 5888–5904. Web of Science CSD CrossRef PubMed CAS Google Scholar
Pervez, H., Chohan, Z. H., Ramzan, M., Nasim, F. H. & Khan, K. M. (2009). J. Enz. Inhib. Med. Chem. 24, 437–446. Web of Science CrossRef CAS Google Scholar
Pervez, H., Iqbal, M. S., Tahir, M. Y., Nasim, F. H., Choudhary, M. I. & Khan, K. M. (2008). J. Enz. Inhib. Med. Chem. 23, 848–854. Web of Science CrossRef CAS Google Scholar
Quenelle, D. C., Keith, K. A. & Kern, E. R. (2006). Antivir. Res. 71, 24–30. Web of Science CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. 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 65| Part 11| November 2009| Pages o2698-o2699

https://doi.org/10.1107/S1600536809040276

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

(Z)-4-Hexyl-1-(5-nitro-2-oxo-2,3-di­hydro-1H-indol-3-yl­­idene)thio­semicarbazide

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

(Z)-4-Hexyl-1-(5-nitro-2-oxo-2,3-dihydro-1H-indol-3-ylidene)thiosemicarbazide