1-(4-Nitro­benzo­yl)thio­semicarbazide monohydrate: a three-dimensional hydrogen-bonded framework structure

Boechat, N.; Lages, A.; Kover, W.B.; Wardell, S.M.S.V.; Skakle, J.M.S.

doi:10.1107/S1600536806019301

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 62| Part 6| June 2006| Pages o2563-o2565

https://doi.org/10.1107/S1600536806019301

1-(4-Nitrobenzoyl)thiosemicarbazide monohydrate: a three-dimensional hydrogen-bonded framework structure

Núbia Boechat,^a Adriana Lages,^a W. Bruce Kover,^b Solange M. S. V. Wardell ^a and Janet M. S. Skakle ^c ^*

^aFundação Oswaldo Cruz, Instituto de Tecnologia em Fármacos, Departamento de Síntese Orgânica, Manguinhos, CEP 21041-250 Rio de Janeiro, RJ, Brazil, ^bDepartamento de Química Oorgânica, Instituto de Química, Universidade Federal do Rio de Janeiro, 21945-970 Rio de Janeiro, RJ, Brazil, and ^cDepartment of Chemistry, College of Physical Sciences, University of Aberdeen, Meston Walk, Aberdeen AB24 3UE, Scotland
^*Correspondence e-mail: j.skakle@abdn.ac.uk

(Received 23 May 2006; accepted 23 May 2006; online 31 May 2006)

In the title compound, C₈H₈N₄O₃S·H₂O, strong hydrogen bonding results in the formation of a number of chains and dimers, which combine to give a three-dimensional hydrogen-bonded framework.

Comment

Acylthiosemicarbazides are versatile compounds, having a large spectrum of biological properties (Bhat et al., 1967 ; Guersoy & Karali, 1995 ; Plumitallo et al., 2004 ). They are, in addition, useful precursors of various biologically active heterocyclic compounds, including triazoles (Kane et al., 1994 ; Palaska et al., 2002 ), thiadiazoles (Oruc et al., 2004 ; Palaska et al., 2002) and oxadiazoles (Palaska et al., 2002; Yale & Losee, 1966 ). Certain acylthiosemicarbazide–transition metal complexes have also been shown to possess useful biological activities (Shen et al., 1997 ; Singh & Singh, 2001 ). As part of our interest in acylthiosemicarbazide compounds, we now report the crystal structure of 1-(4-nitrobenzoyl)thiosemicarbazide monohydrate, (I).

Within the asymmetric unit of (I), the O atom of the solvent water molecule acts as an H-atom acceptor for the amide group of the organic molecule (Fig. 1). The p-nitro group is rotated from the essentially planar aryl group by an angle of 13.07 (12)°, whereas the CN(O) group is twisted by 10.77 (12)°.

The hydrogen bonding (Table 2) at the basic level produces a mixture of chains and dimers. The combination of the hydrogen bond described above, together with O1W—H1WA⋯O7ⁱⁱ [symmetry code: (ii) x + 1, y, z] leads to a C₂²(9) chain (Bernstein et al., 1995 ) along [010]. Another chain, C(12), forms along [100] via the N9—H9A⋯O42^vhydrogen bond [symmetry code: (v) x, y, z − 1]. These combine to form an R₅⁶(34) ring (Fig. 2); the disparity between the number of donors and acceptors results from the amide acting as a double donor. The rings link to create a sheet normal to [010] (Fig. 2).

All other hydrogen bonds involve S as an acceptor and result in dimers. In the first, the hydrogen bond within the asymmetric unit combines with O1W—H1WA⋯S1¹ [symmetry code: (i) 1 − x, 1 − y, −z] to form an R₄⁴(12) ring. The other two are simpler motifs; N7—H7⋯S1ⁱⁱⁱ [symmetry code: (iii) 1 − x, 2 − y, −z] giving an R₂²(10) ring and N8—H8⋯S1^iv [symmetry code: (iv) −x, 2 − y, −z] forming an R₂²(8) motif. The former two dimers combine with the above-described hydrogen bond to give a chain along [010] (Fig. 3). The sheet shown in Fig. 2 and the chain shown in Fig. 3 thus combine to give a three-dimensional hydrogen-bonded framework.

Figure 1
The molecular structure of the title compound, showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are shown as circles of arbitrary radius. The dashed line indicates a hydrogen bond.

Figure 2
Part of the crystal structure of (I)

, showing the formation of a hydrogen-bonded R₅⁶(34) ring which links with others to give sheets. Atoms marked with (ii), (v) or a hash (#) are at the symmetry positions (1 + x, y, z), (x, y, −1 + z) and (1 + x, y, −1 + z), respectively. Dashed lines indicate hydrogen bonds.

Figure 3
Part of the crystal structure of (I)

, showing the formation of hydrogen-bonded dimers linked to form a chain. Atoms marked with (i), (iii) or an asterisk (*) are at the symmetry positions (1 − x, 1 − y, −z), (1 − x, 2 − y, −z) and (x, 1 + y, z) respectively. Dashed lines indicate hydrogen bonds.

Experimental

A solution of potassium thiocyanate (0.73 g, 12.5 mmol) and concentrated HCl (1.25 ml) was added to a stirred solution of 4-nitrobenzoylhydrazide (1.5 g, 8.3 mmol) (Hosamani & Pattanashettar, 2004 ) in methanol (21 ml). The mixture was evaporated to dryness on a steam bath, further methanol (21 ml) was added and the mixture heated for 1 h on a steam bath. The resulting solid was successively washed with water and a small volume of ethanol, and recrystallized from acetone, yielding 2.1 g (70%) of yellow 1-(4-nitrobenzoyl)thiosemicarbazide (m.p. 489 K). ¹H NMR (500 MHz, DMSO-d₆): δ 10.71 (s, 1H, CONHNH), 9.44 (s, 1H, CONH), 8.33 (d, 2H, J = 8.5 Hz, Ar—H), 8.13 (d, 2H, J = 8.5 Hz, Ar—H), 7.95 (s, 1H, CSNH₂), 7.79 (s, 1H, CSNH₂).

Crystal data

C₈H₈N₄O₃S·H₂O
M_r = 258.26
Triclinic, $[P \overline 1]$
a = 6.0621 (2) Å
b = 7.3991 (3) Å
c = 12.2661 (5) Å
α = 75.9684 (16)°
β = 85.112 (2)°
γ = 88.903 (2)°
V = 531.83 (4) Å³
Z = 2
D_x = 1.613 Mg m⁻³
Mo Kα radiation
μ = 0.32 mm⁻¹
T = 120 (2) K
Slab, pale yellow
0.45 × 0.45 × 0.10 mm

Data collection

Bruker–Nonius KappaCCD diffractometer
φ and ω scans
Absorption correction: multi-scan (SADABS; Sheldrick, 2003 ) T_min = 0.688, T_max = 0.928
8670 measured reflections
2425 independent reflections
2178 reflections with I > 2σ(I)
R_int = 0.028
θ_max = 27.6°

Refinement

Refinement on F²
R[F² > 2σ(F²)] = 0.031
wR(F²) = 0.091
S = 1.12
2425 reflections
172 parameters
H atoms treated by a mixture of independent and constrained refinement
w = 1/[σ²(F_o²) + (0.0474P)² + 0.2095P] where P = (F_o² + 2F_c²)/3
(Δ/σ)_max < 0.001
Δρ_max = 0.37 e Å⁻³
Δρ_min = −0.38 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1WA⋯S1ⁱ	0.79 (2)	2.61 (2)	3.3472 (13)	156.5 (18)
O1W—H1WA⋯O7ⁱⁱ	0.81 (2)	2.01 (2)	2.7944 (15)	162.7 (19)
N7—H7⋯S1ⁱⁱⁱ	0.831 (19)	2.608 (19)	3.4096 (13)	162.4 (16)
N8—H8⋯S1^iv	0.854 (19)	2.49 (2)	3.3382 (13)	172.0 (16)
N9—H9A⋯O42^v	0.84 (2)	2.26 (2)	3.0834 (17)	164.8 (18)
N9—H9B⋯O1W	0.89 (2)	1.94 (2)	2.7754 (16)	153.8 (17)
Symmetry codes: (i) -x+1, -y+1, -z; (ii) x+1, y, z; (iii) -x+1, -y+2, -z; (iv) -x, -y+2, -z; (v) x, y, z-1.

All H atoms were located in difference maps; those in the aryl ring were then treated as riding atoms, with C—H = 0.95 Å and U_iso(H) = 1.2U_eq(C). All other H atoms were refined freely.

Data collection: COLLECT (Hooft, 1998 ); cell refinement: DENZO (Otwinowski & Minor, 1997 ) and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: OSCAIL (McArdle, 2003 ) and SHELXS97 (Sheldrick, 1997 ); program(s) used to refine structure: OSCAIL and SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ); software used to prepare material for publication: CIFTAB (Sheldrick, 1997) and PLATON (Spek, 2003 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536806019301/lh2086sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536806019301/lh2086Isup2.hkl

Computing details top

Data collection: COLLECT (Hooft, 1998); cell refinement: DENZO (Otwinowski & Minor, 1997) and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: OSCAIL (McArdle, 2003) and SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: OSCAIL and SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: CIFTAB (Sheldrick, 1997).

1-(4-Nitrobenzoyl)thiosemicarbazide monohydrate top

Crystal data top

C₈H₈N₄O₃S·H₂O	Z = 2
M_r = 258.26	F(000) = 268
Triclinic, P1	D_x = 1.613 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.0621 (2) Å	Cell parameters from 2242 reflections
b = 7.3991 (3) Å	θ = 2.9–27.5°
c = 12.2661 (5) Å	µ = 0.32 mm⁻¹
α = 75.9684 (16)°	T = 120 K
β = 85.112 (2)°	Slab, pale yellow
γ = 88.903 (2)°	0.45 × 0.45 × 0.10 mm
V = 531.83 (4) Å³

Data collection top

Bruker–Nonius KappaCCD diffractometer	2425 independent reflections
Radiation source: Bruker–Nonius KappaCCD	2178 reflections with I > 2σ(I)
10 cm confocal mirrors monochromator	R_int = 0.028
Detector resolution: 9.091 pixels mm^-1	θ_max = 27.6°, θ_min = 3.4°
φ and ω scans	h = −7→7
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	k = −9→9
T_min = 0.688, T_max = 0.928	l = −15→15
8670 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)] = 0.031	Hydrogen site location: difference Fourier map
wR(F²) = 0.091	H atoms treated by a mixture of independent and constrained refinement
S = 1.12	w = 1/[σ²(F_o²) + (0.0474P)² + 0.2095P] where P = (F_o² + 2F_c²)/3
2425 reflections	(Δ/σ)_max < 0.001
172 parameters	Δρ_max = 0.37 e Å⁻³
0 restraints	Δρ_min = −0.38 e Å⁻³

Special details top

Experimental. IR ν_max (KBr, cm^-1): 3515, 3429, 3157, 1683, 1630, 1605, 1522, 1348, 1264, 714. ¹³C NMR (125 MHz, DMSO-d₆): δ 181.92, 164.30, 149.20, 138.24, 129.30, 123.22.

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
C1	0.4146 (2)	0.75286 (19)	0.39533 (11)	0.0124 (3)
C2	0.6269 (2)	0.82803 (19)	0.38368 (11)	0.0145 (3)
H2	0.6979	0.8770	0.3106	0.019*
C3	0.7348 (2)	0.83152 (19)	0.47840 (12)	0.0141 (3)
H3	0.8784	0.8843	0.4714	0.018*
C4	0.6275 (2)	0.75598 (19)	0.58338 (11)	0.0129 (3)
C5	0.4188 (2)	0.67728 (19)	0.59826 (12)	0.0143 (3)
H5	0.3507	0.6251	0.6716	0.019*
C6	0.3118 (2)	0.67690 (19)	0.50267 (12)	0.0134 (3)
H6	0.1677	0.6247	0.5103	0.017*
N4	0.74170 (19)	0.75903 (17)	0.68434 (10)	0.0156 (3)
O41	0.90680 (19)	0.85720 (17)	0.67255 (9)	0.0266 (3)
O42	0.66489 (18)	0.66376 (17)	0.77561 (9)	0.0242 (3)
C7	0.2872 (2)	0.74619 (19)	0.29655 (11)	0.0128 (3)
O7	0.11625 (16)	0.65565 (15)	0.30868 (9)	0.0186 (2)
N7	0.3713 (2)	0.84764 (17)	0.19467 (10)	0.0142 (3)
H7	0.476 (3)	0.921 (3)	0.1890 (15)	0.018*
N8	0.2502 (2)	0.86376 (18)	0.10162 (10)	0.0156 (3)
H8	0.133 (3)	0.930 (3)	0.0979 (15)	0.020*
C8	0.3325 (2)	0.80758 (19)	0.01032 (11)	0.0131 (3)
N9	0.5224 (2)	0.71739 (18)	0.01309 (11)	0.0177 (3)
H9A	0.574 (3)	0.684 (3)	−0.0449 (17)	0.023*
H9B	0.598 (3)	0.689 (3)	0.0745 (17)	0.023*
S1	0.18825 (6)	0.85785 (5)	−0.10755 (3)	0.01538 (12)
O1W	0.83048 (19)	0.56199 (16)	0.16378 (10)	0.0208 (2)
H1WA	0.932 (3)	0.595 (3)	0.1938 (17)	0.027*
H1WA	0.867 (3)	0.468 (3)	0.1476 (17)	0.027*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0146 (6)	0.0122 (6)	0.0116 (6)	0.0024 (5)	−0.0043 (5)	−0.0042 (5)
C2	0.0157 (7)	0.0159 (7)	0.0109 (6)	−0.0004 (5)	−0.0020 (5)	−0.0008 (5)
C3	0.0125 (6)	0.0145 (7)	0.0157 (7)	−0.0013 (5)	−0.0033 (5)	−0.0032 (5)
C4	0.0162 (7)	0.0135 (6)	0.0107 (6)	0.0035 (5)	−0.0054 (5)	−0.0053 (5)
C5	0.0160 (7)	0.0153 (7)	0.0115 (6)	0.0015 (5)	−0.0006 (5)	−0.0033 (5)
C6	0.0120 (6)	0.0137 (6)	0.0146 (7)	0.0004 (5)	−0.0014 (5)	−0.0035 (5)
N4	0.0160 (6)	0.0195 (6)	0.0134 (6)	0.0036 (5)	−0.0042 (4)	−0.0071 (5)
O41	0.0258 (6)	0.0332 (7)	0.0223 (6)	−0.0090 (5)	−0.0111 (4)	−0.0060 (5)
O42	0.0260 (6)	0.0371 (7)	0.0093 (5)	−0.0008 (5)	−0.0023 (4)	−0.0049 (5)
C7	0.0137 (6)	0.0138 (6)	0.0119 (6)	0.0029 (5)	−0.0029 (5)	−0.0049 (5)
O7	0.0153 (5)	0.0252 (6)	0.0158 (5)	−0.0047 (4)	−0.0040 (4)	−0.0046 (4)
N7	0.0136 (6)	0.0192 (6)	0.0107 (6)	−0.0024 (5)	−0.0044 (4)	−0.0040 (5)
N8	0.0151 (6)	0.0218 (6)	0.0111 (6)	0.0038 (5)	−0.0067 (4)	−0.0050 (5)
C8	0.0157 (7)	0.0116 (6)	0.0112 (6)	−0.0032 (5)	−0.0021 (5)	−0.0009 (5)
N9	0.0192 (6)	0.0238 (7)	0.0121 (6)	0.0066 (5)	−0.0059 (5)	−0.0071 (5)
S1	0.0180 (2)	0.0187 (2)	0.01036 (19)	0.00160 (13)	−0.00624 (13)	−0.00371 (13)
O1W	0.0208 (6)	0.0193 (6)	0.0236 (6)	−0.0006 (4)	−0.0108 (4)	−0.0047 (5)

Geometric parameters (Å, º) top

C1—C2	1.3943 (19)	N4—O42	1.2281 (16)
C1—C6	1.3973 (19)	C7—O7	1.2234 (17)
C1—C7	1.5022 (18)	C7—N7	1.3551 (18)
C2—C3	1.3867 (19)	N7—N8	1.3890 (16)
C2—H2	0.9500	N7—H7	0.831 (19)
C3—C4	1.3840 (19)	N8—C8	1.3411 (18)
C3—H3	0.9500	N8—H8	0.854 (19)
C4—C5	1.382 (2)	C8—N9	1.3180 (18)
C4—N4	1.4742 (17)	C8—S1	1.7135 (14)
C5—C6	1.3882 (19)	N9—H9A	0.84 (2)
C5—H5	0.9500	N9—H9B	0.89 (2)
C6—H6	0.9500	O1W—H1WA	0.81 (2)
N4—O41	1.2257 (16)	O1W—H1WA	0.79 (2)

C2—C1—C6	120.01 (12)	O41—N4—C4	118.21 (11)
C2—C1—C7	123.07 (12)	O42—N4—C4	118.00 (12)
C6—C1—C7	116.92 (12)	O7—C7—N7	122.55 (12)
C3—C2—C1	120.21 (12)	O7—C7—C1	121.35 (12)
C3—C2—H2	119.9	N7—C7—C1	116.10 (12)
C1—C2—H2	119.9	C7—N7—N8	119.14 (12)
C4—C3—C2	118.22 (12)	C7—N7—H7	121.3 (12)
C4—C3—H3	120.9	N8—N7—H7	117.8 (13)
C2—C3—H3	120.9	C8—N8—N7	121.51 (12)
C5—C4—C3	123.23 (13)	C8—N8—H8	119.3 (12)
C5—C4—N4	118.35 (12)	N7—N8—H8	118.1 (12)
C3—C4—N4	118.42 (12)	N9—C8—N8	119.39 (13)
C4—C5—C6	117.89 (13)	N9—C8—S1	121.85 (11)
C4—C5—H5	121.1	N8—C8—S1	118.75 (10)
C6—C5—H5	121.1	C8—N9—H9A	118.7 (13)
C5—C6—C1	120.44 (13)	C8—N9—H9B	122.6 (12)
C5—C6—H6	119.8	H9A—N9—H9B	118.7 (17)
C1—C6—H6	119.8	H1WA—O1W—H1WA	107 (2)
O41—N4—O42	123.78 (12)

C6—C1—C2—C3	−1.5 (2)	C5—C4—N4—O42	12.54 (18)
C7—C1—C2—C3	179.39 (12)	C3—C4—N4—O42	−167.28 (13)
C1—C2—C3—C4	1.1 (2)	C2—C1—C7—O7	169.10 (13)
C2—C3—C4—C5	0.1 (2)	C6—C1—C7—O7	−10.07 (19)
C2—C3—C4—N4	179.88 (12)	C2—C1—C7—N7	−11.73 (19)
C3—C4—C5—C6	−0.9 (2)	C6—C1—C7—N7	169.10 (12)
N4—C4—C5—C6	179.33 (11)	O7—C7—N7—N8	5.9 (2)
C4—C5—C6—C1	0.5 (2)	C1—C7—N7—N8	−173.27 (11)
C2—C1—C6—C5	0.6 (2)	C7—N7—N8—C8	−121.29 (15)
C7—C1—C6—C5	179.85 (12)	N7—N8—C8—N9	7.2 (2)
C5—C4—N4—O41	−167.02 (13)	N7—N8—C8—S1	−172.06 (10)
C3—C4—N4—O41	13.16 (19)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1WA···S1ⁱ	0.79 (2)	2.61 (2)	3.3472 (13)	156.5 (18)
O1W—H1WA···O7ⁱⁱ	0.81 (2)	2.01 (2)	2.7944 (15)	162.7 (19)
N7—H7···S1ⁱⁱⁱ	0.831 (19)	2.608 (19)	3.4096 (13)	162.4 (16)
N8—H8···S1^iv	0.854 (19)	2.49 (2)	3.3382 (13)	172.0 (16)
N9—H9A···O42^v	0.84 (2)	2.26 (2)	3.0834 (17)	164.8 (18)
N9—H9B···O1W	0.89 (2)	1.94 (2)	2.7754 (16)	153.8 (17)

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

Acknowledgements

We are indebted to the EPSRC for the use of both the Chemical Database Service at Daresbury, England, primarily for access to the Cambridge Structural Database (Fletcher et al., 1996 ), and the X-ray service at the University of Southampton, England, for data collection.

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