Crystal structure of N′-[(1E)-1-(6-methyl-2,4-dioxo-3,4-di­hydro-2H-pyran-3-yl­idene)eth­yl]benzene­sulfono­hydrazide

Asegbeloyin, J.N.; Ujam, O.T.; Ngige, C.M.; Onwukeme, V.I.; Groutso, T.

doi:10.1107/S1600536814022648

organic compounds

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Volume 70| Part 11| November 2014| Pages o1179-o1180

doi:10.1107/S1600536814022648

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Crystal structure of N′-[(1E)-1-(6-methyl-2,4-dioxo-3,4-dihydro-2H-pyran-3-ylidene)ethyl]benzenesulfonohydrazide

Jonnie N. Asegbeloyin,^a Oguejiofo T. Ujam,^a ^* Chizoba M. Ngige,^b Valentine I. Onwukeme ^b and Tania Groutso ^c

^aDepartment of Pure and Industrial Chemistry, University of Nigeria, Nsukka, Enugu State, Nigeria, ^bDepartment of Pure and Industrial Chemistry, Nnamdi Azikiwe University, PMB 5025, Awka, Anambra State, Nigeria, and ^cSchool of Chemical Sciences, the University of Auckland Private Bag 92019, Auckland 1142, New Zealand
^*Correspondence e-mail: oguejiofo.ujam@unn.edu.ng

Edited by M. Weil, Vienna University of Technology, Austria (Received 1 October 2014; accepted 15 October 2014; online 24 October 2014)

In the title compound, C₁₄H₁₄N₂O₅S, the molecule exists in the enamine (C=C—NH) tautomeric form. The hydrazone fragment derived from the 3-acetyl-4-hydroxy-6-methyl-2H-pyran-2-one moiety is approximately planar, with a maximum deviation of 0.1291 (11) Å for the N atom bound to the S atom of the benzensulfonohydrazide group. The latter adopts a gauche conformation relative to the hydrazone N—N bond, with an N—N—S angle of 113.54 (10)°. There is an intramolecular N—H⋯O=C hydrogen bond that stabilizes the tautomeric form. In the crystal, molecules are linked by N—H⋯O=C hydrogen bonds into chains extending parallel to [100].

Keywords: crystal structure; hydrazone; benzenesulfonohydrazide; enamine tautomeric form; hydrogen bonds.

CCDC reference: 1029366

1. Related literature

3-Acetyl-4-hydroxy-6-methyl-2H-pyran-2-one and its derivatives have received attention due to their coordination chemistry, pharmaceutical significance and biologically activities (Battaini et al., 2000 ; Puerta & Cohen, 2003 ; Rao & Narasaiah, 2003 ; Zucolotto Chalaça et al., 2002 ; Fouad et al., 2010 ; Kubaisi & Ismail, 1994 ; Rao et al., 1985 ; Deshmukh et al., 2010a ,b ; Munde et al., 2009 , 2010 ; Faidallah et al., 2011 ; Jadhav et al., 2010 ). 3-Acetyl-4-hydroxy-6-methyl-2H-pyran-2-one is also well-noted for its fungicidal (Rao et al., 1978 ), herbicidal and antimicrobial activities (Zucolotto Chalaça et al., 2002). The title compound is a new hydrazone prepared as part of an on-going research to study the ligating ability and antimicrobial properties of 3-acetyl-4-hydroxy-6-methyl-2H-pyran-2-one hydrazones and their derivatives. For the crystal structure of a related thiosemicarbazone, see: Vrdoljak et al. (2008 ). For a benzenesulfonohydrazide derivative of a similar tautomeric enamine form, see: Ukwueze et al. (2014 ).

2. Experimental

2.1. Crystal data

C₁₄H₁₄N₂O₅S
M_r = 322.33
Monoclinic, P 2₁ /n
a = 7.4797 (4) Å
b = 15.2458 (7) Å
c = 12.7820 (6) Å
β = 94.282 (3)°
V = 1453.51 (12) Å³
Z = 4
Mo Kα radiation
μ = 0.25 mm⁻¹
T = 99 K
0.30 × 0.30 × 0.12 mm

2.2. Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2003 ) T_min = 0.659, T_max = 0.746
17170 measured reflections
3484 independent reflections
2817 reflections with I > 2σ(I)
R_int = 0.056

2.3. Refinement

R[F² > 2σ(F²)] = 0.043
wR(F²) = 0.126
S = 1.05
3484 reflections
209 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.35 e Å⁻³
Δρ_min = −0.42 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—HN1⋯O4ⁱ	0.89 (2)	1.89 (2)	2.7837 (19)	175 (2)
N2—HN2⋯O3	0.90 (2)	1.74 (2)	2.5194 (18)	144 (2)
Symmetry code: (i) x-1, y, z.

Data collection: APEX2 (Bruker, 2004 ); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ) and Mercury (Macrae et al., 2006 ); software used to prepare material for publication: WinGX (Farrugia, 2012).

Supporting information

CCDC reference: 1029366

Crystal structure: contains datablock I. DOI: 10.1107/S1600536814022648/wm5072sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814022648/wm5072Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536814022648/wm5072Isup3.mol

Supporting information file. DOI: 10.1107/S1600536814022648/wm5072Isup4.cml

checkCIF report

Synthesis and Crystallisation top

A solution of 3-acetyl-4-hydroxy-6-methyl-(2H)-pyran-2-one [168 mg, 1 mmol] in methanol (10 ml) was mixed with a solution of benzenesulfonohydrazide [172 mg, 1 mmol] in methanol (10 ml). The mixture was refluxed for 3 h, and the resulting solution cooled to obtain a white precipitate. The product was filtered, dried and recrystallized from methanol. Crystals suitable for X-ray crystallographic analysis were obtained by slow evaporation of a methanolic solution at room temperature for 48 h.

Refinement top

Crystal data, data collection and structure refinement details are summarized in Table 2. Hydrogen atoms were placed in calculated positions with C—H = 0.95 - 0.98 Å and refined using a riding model with displacement parameters U_iso(H) = 1.2 U_eq(C) for aromatic and methylene groups and U_iso(H) = 1.5 U_eq(C) for methyl groups. The two N—H hydrogen atoms were located in a difference map and were refined freely.

Related literature top

3-Acetyl-4-hydroxy-6-methyl-2H-pyran-2-one and its derivatives have received attention due to their coordination chemistry, pharmaceutical significance and biologically activities (Battaini et al., 2000; Puerta & Cohen, 2003; Rao & Narasaiah, 2003; Zucolotto Chalaça et al., 2002; Fouad et al., 2010; Kubaisi & Ismail, 1994; Rao et al., 1985; Deshmukh et al., 2010a,b; Munde et al., 2009, 2010; Faidallah et al., 2011; Jadhav et al., 2010). 3-Acetyl-4-hydroxy-6-methyl-2H-pyran-2-one is also well-noted for its fungicidal (Rao et al., 1978), herbicidal and antimicrobial activities (Zucolotto Chalaça et al., 2002). The title compound is a new hydrazone prepared as part of an on-going research to study the ligating ability and antimicrobial properties of 3-acetyl-4-hydroxy-6-methyl-2H-pyran-2-one hydrazones and their derivatives. For the crystal structure of a related thiosemicarbazone, see: Vrdoljak et al. (2008). For a benzenesulfonohydrazide derivative of a similar tautomeric enamine form, see: Ukwueze et al. (2014).

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae et al., 2006); software used to prepare material for publication: WinGX (Farrugia, 2012).

Figures top

The molecular structure and atom numbering of the title compound with displacement ellipsoids drawn at the 50% probability level for non-H atoms.

Intramolecular N2–Hn2···O3 and intermolecular N1–Hn1···O4 (dotted lines) hydrogen bonding interactions in the title compound. [Symmetry codes: i) 1+x, y, z; ii) -1+x, y, z; iii) -2+x, y, z.]

The packing diagram of the title compound showing intra- and intermolecular N—H···O═C hydrogen bonds as dotted lines.

N'-[(1E)-1-(6-Methyl-2,4-dioxo-3,4-dihydro-2H-pyran-3-ylidene)ethyl]benzenesulfonohydrazide top

Crystal data top

C₁₄H₁₄N₂O₅S	F(000) = 672
M_r = 322.33	D_x = 1.473 Mg m⁻³
Monoclinic, P2₁/n	Melting point: 473 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 7.4797 (4) Å	Cell parameters from 5140 reflections
b = 15.2458 (7) Å	θ = 2.7–28.0°
c = 12.7820 (6) Å	µ = 0.25 mm⁻¹
β = 94.282 (3)°	T = 99 K
V = 1453.51 (12) Å³	Needle, colourless
Z = 4	0.30 × 0.30 × 0.12 mm

Data collection top

Bruker APEXII CCD diffractometer	3484 independent reflections
Radiation source: fine-focus sealed tube	2817 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.056
ϕ and ω scans	θ_max = 28.0°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	h = −9→9
T_min = 0.659, T_max = 0.746	k = −20→19
17170 measured reflections	l = −16→16

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.043	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.126	w = 1/[σ²(F_o²) + (0.0681P)² + 0.4046P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max < 0.001
3484 reflections	Δρ_max = 0.35 e Å⁻³
209 parameters	Δρ_min = −0.41 e Å⁻³

Crystal data top

C₁₄H₁₄N₂O₅S	V = 1453.51 (12) Å³
M_r = 322.33	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 7.4797 (4) Å	µ = 0.25 mm⁻¹
b = 15.2458 (7) Å	T = 99 K
c = 12.7820 (6) Å	0.30 × 0.30 × 0.12 mm
β = 94.282 (3)°

Data collection top

Bruker APEXII CCD diffractometer	3484 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	2817 reflections with I > 2σ(I)
T_min = 0.659, T_max = 0.746	R_int = 0.056
17170 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.043	0 restraints
wR(F²) = 0.126	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	Δρ_max = 0.35 e Å⁻³
3484 reflections	Δρ_min = −0.41 e Å⁻³
209 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.

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

	x	y	z	U_iso*/U_eq
C1	−0.1162 (3)	0.17867 (12)	−0.16895 (13)	0.0281 (4)
H1	0.0092	0.1698	−0.1554	0.034*
C2	−0.2300 (3)	0.10824 (12)	−0.19238 (14)	0.0326 (4)
H2	−0.1824	0.0505	−0.1945	0.039*
C3	−0.4125 (3)	0.12162 (13)	−0.21263 (13)	0.0321 (4)
H3	−0.4890	0.0732	−0.2298	0.038*
C4	−0.4844 (3)	0.20534 (13)	−0.20807 (13)	0.0322 (4)
H4	−0.6099	0.2139	−0.2211	0.039*
C5	−0.3730 (3)	0.27633 (12)	−0.18449 (12)	0.0280 (4)
H5	−0.4214	0.3338	−0.1812	0.034*
C6	−0.1896 (2)	0.26269 (11)	−0.16563 (12)	0.0237 (4)
C7	0.2970 (2)	0.31837 (11)	0.04228 (12)	0.0216 (3)
C8	0.3518 (2)	0.41187 (11)	0.02935 (15)	0.0289 (4)
H8A	0.2446	0.4487	0.0183	0.043*
H8B	0.4239	0.4169	−0.0313	0.043*
H8C	0.4228	0.4313	0.0926	0.043*
C9	0.4199 (2)	0.24839 (10)	0.06583 (11)	0.0206 (3)
C10	0.3574 (2)	0.15821 (10)	0.06591 (12)	0.0227 (3)
C11	0.4934 (2)	0.09113 (11)	0.08080 (12)	0.0231 (3)
H11	0.4581	0.0313	0.0802	0.028*
C12	0.6670 (2)	0.11099 (11)	0.09535 (12)	0.0256 (4)
C13	0.8158 (2)	0.04793 (13)	0.11667 (16)	0.0351 (4)
H13A	0.8639	0.0538	0.1898	0.053*
H13B	0.9108	0.0602	0.0699	0.053*
H13C	0.7713	−0.0119	0.1045	0.053*
C14	0.6075 (2)	0.26625 (11)	0.08402 (12)	0.0231 (3)
N1	−0.0028 (2)	0.35893 (9)	−0.00836 (11)	0.0236 (3)
N2	0.12527 (19)	0.29758 (9)	0.03004 (10)	0.0223 (3)
O1	0.12058 (18)	0.33764 (9)	−0.18100 (10)	0.0336 (3)
O2	−0.14865 (19)	0.43127 (8)	−0.16350 (10)	0.0361 (3)
O3	0.19542 (17)	0.13680 (8)	0.05307 (10)	0.0289 (3)
O4	0.68037 (16)	0.33852 (8)	0.09030 (10)	0.0293 (3)
O5	0.72498 (16)	0.19616 (8)	0.09491 (9)	0.0260 (3)
S	−0.04830 (6)	0.35372 (3)	−0.13822 (3)	0.02574 (15)
HN1	−0.102 (3)	0.3549 (13)	0.0260 (16)	0.033 (5)*
HN2	0.100 (3)	0.2408 (16)	0.0391 (17)	0.046 (6)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0314 (10)	0.0252 (8)	0.0276 (8)	0.0063 (7)	0.0026 (7)	0.0010 (6)
C2	0.0455 (11)	0.0217 (8)	0.0306 (9)	0.0031 (8)	0.0026 (8)	−0.0002 (7)
C3	0.0413 (11)	0.0308 (9)	0.0238 (8)	−0.0067 (8)	0.0004 (8)	0.0004 (7)
C4	0.0305 (10)	0.0400 (10)	0.0255 (8)	0.0011 (8)	−0.0013 (7)	−0.0011 (7)
C5	0.0327 (10)	0.0274 (9)	0.0237 (8)	0.0071 (8)	0.0011 (7)	−0.0002 (6)
C6	0.0305 (9)	0.0222 (8)	0.0185 (7)	0.0029 (7)	0.0023 (7)	0.0014 (6)
C7	0.0237 (8)	0.0223 (8)	0.0198 (7)	−0.0050 (6)	0.0076 (6)	−0.0039 (6)
C8	0.0258 (9)	0.0192 (8)	0.0423 (10)	−0.0029 (7)	0.0068 (8)	−0.0026 (7)
C9	0.0222 (8)	0.0201 (8)	0.0200 (7)	−0.0036 (6)	0.0059 (6)	−0.0018 (6)
C10	0.0267 (9)	0.0221 (8)	0.0196 (7)	−0.0037 (7)	0.0051 (6)	−0.0011 (6)
C11	0.0256 (9)	0.0186 (7)	0.0255 (7)	−0.0025 (6)	0.0044 (7)	0.0004 (6)
C12	0.0307 (9)	0.0226 (8)	0.0242 (7)	−0.0012 (7)	0.0061 (7)	−0.0005 (6)
C13	0.0269 (10)	0.0306 (10)	0.0476 (11)	0.0019 (8)	0.0015 (8)	−0.0021 (8)
C14	0.0246 (9)	0.0223 (8)	0.0231 (7)	−0.0015 (7)	0.0061 (6)	−0.0035 (6)
N1	0.0219 (7)	0.0230 (7)	0.0265 (7)	0.0009 (6)	0.0059 (6)	−0.0017 (5)
N2	0.0213 (7)	0.0210 (7)	0.0251 (6)	−0.0014 (6)	0.0051 (5)	0.0000 (5)
O1	0.0352 (7)	0.0369 (7)	0.0303 (6)	−0.0015 (6)	0.0129 (6)	0.0034 (5)
O2	0.0450 (8)	0.0206 (6)	0.0422 (7)	0.0044 (6)	−0.0010 (6)	0.0050 (5)
O3	0.0245 (6)	0.0243 (6)	0.0380 (7)	−0.0073 (5)	0.0031 (5)	0.0003 (5)
O4	0.0221 (6)	0.0243 (6)	0.0421 (7)	−0.0050 (5)	0.0072 (5)	−0.0061 (5)
O5	0.0227 (6)	0.0239 (6)	0.0318 (6)	−0.0020 (5)	0.0051 (5)	−0.0020 (5)
S	0.0308 (3)	0.0203 (2)	0.0266 (2)	0.00152 (17)	0.00559 (18)	0.00282 (14)

Geometric parameters (Å, º) top

C1—C2	1.389 (3)	C9—C10	1.452 (2)
C1—C6	1.396 (2)	C10—O3	1.254 (2)
C1—H1	0.9500	C10—C11	1.445 (2)
C2—C3	1.386 (3)	C11—C12	1.332 (2)
C2—H2	0.9500	C11—H11	0.9500
C3—C4	1.388 (3)	C12—O5	1.369 (2)
C3—H3	0.9500	C12—C13	1.481 (3)
C4—C5	1.386 (3)	C13—H13A	0.9800
C4—H4	0.9500	C13—H13B	0.9800
C5—C6	1.391 (3)	C13—H13C	0.9800
C5—H5	0.9500	C14—O4	1.229 (2)
C6—S	1.7635 (18)	C14—O5	1.384 (2)
C7—N2	1.321 (2)	N1—N2	1.401 (2)
C7—C9	1.426 (2)	N1—S	1.6712 (15)
C7—C8	1.496 (2)	N1—HN1	0.89 (2)
C8—H8A	0.9800	N2—HN2	0.90 (2)
C8—H8B	0.9800	O1—S	1.4345 (13)
C8—H8C	0.9800	O2—S	1.4246 (13)
C9—C14	1.431 (2)

C2—C1—C6	118.68 (17)	O3—C10—C9	123.66 (15)
C2—C1—H1	120.7	C11—C10—C9	116.55 (15)
C6—C1—H1	120.7	C12—C11—C10	121.76 (15)
C3—C2—C1	120.40 (17)	C12—C11—H11	119.1
C3—C2—H2	119.8	C10—C11—H11	119.1
C1—C2—H2	119.8	C11—C12—O5	121.38 (16)
C2—C3—C4	120.47 (18)	C11—C12—C13	126.11 (16)
C2—C3—H3	119.8	O5—C12—C13	112.47 (15)
C4—C3—H3	119.8	C12—C13—H13A	109.5
C5—C4—C3	119.92 (18)	C12—C13—H13B	109.5
C5—C4—H4	120.0	H13A—C13—H13B	109.5
C3—C4—H4	120.0	C12—C13—H13C	109.5
C4—C5—C6	119.38 (16)	H13A—C13—H13C	109.5
C4—C5—H5	120.3	H13B—C13—H13C	109.5
C6—C5—H5	120.3	O4—C14—O5	114.24 (15)
C5—C6—C1	121.14 (17)	O4—C14—C9	127.28 (16)
C5—C6—S	119.04 (13)	O5—C14—C9	118.48 (14)
C1—C6—S	119.81 (14)	N2—N1—S	113.54 (10)
N2—C7—C9	116.83 (14)	N2—N1—HN1	110.8 (13)
N2—C7—C8	119.20 (16)	S—N1—HN1	111.7 (14)
C9—C7—C8	123.96 (15)	C7—N2—N1	120.97 (14)
C7—C8—H8A	109.5	C7—N2—HN2	115.3 (16)
C7—C8—H8B	109.5	N1—N2—HN2	123.2 (16)
H8A—C8—H8B	109.5	C12—O5—C14	122.25 (13)
C7—C8—H8C	109.5	O2—S—O1	121.29 (8)
H8A—C8—H8C	109.5	O2—S—N1	104.51 (8)
H8B—C8—H8C	109.5	O1—S—N1	105.48 (8)
C7—C9—C14	120.05 (14)	O2—S—C6	108.08 (8)
C7—C9—C10	120.42 (15)	O1—S—C6	108.75 (8)
C14—C9—C10	119.45 (15)	N1—S—C6	108.02 (7)
O3—C10—C11	119.79 (14)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—HN1···O4ⁱ	0.89 (2)	1.89 (2)	2.7837 (19)	175 (2)
N2—HN2···O3	0.90 (2)	1.74 (2)	2.5194 (18)	144 (2)

Symmetry code: (i) x−1, y, z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—HN1···O4ⁱ	0.89 (2)	1.89 (2)	2.7837 (19)	175 (2)
N2—HN2···O3	0.90 (2)	1.74 (2)	2.5194 (18)	144 (2)

Symmetry code: (i) x−1, y, z.

Acknowledgements

We thank the Department of Pure and Industrial Chemistry, University of Nigeria, Nsukka, Enugu State, Nigeria, for financial assistance, the Department of Chemistry, University of Auckland, New Zealand, where the data were collected, and Nkechinyere N. Ukwueze for a generous donation of benzenesulfonohydrazide.

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Volume 70| Part 11| November 2014| Pages o1179-o1180

doi:10.1107/S1600536814022648

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

Crystal structure of N′-[(1E)-1-(6-methyl-2,4-dioxo-3,4-di­hydro-2H-pyran-3-yl­­idene)eth­yl]benzene­sulfono­hydrazide

1. Related literature

2. Experimental

2.1. Crystal data

2.2. Data collection

2.3. Refinement

Supporting information

Acknowledgements

References

organic compounds

Crystal structure of N′-[(1E)-1-(6-methyl-2,4-dioxo-3,4-dihydro-2H-pyran-3-ylidene)ethyl]benzenesulfonohydrazide