4-[4-Eth­oxy­carbonyl-5-(3,4-methyl­ene­dioxy­phen­yl)-3-oxocyclo­hex-1-en-1-yl]-3-phenyl­sydnone

Fun, H.-K.; Loh, W.-S.; Nithinchandra; Kalluraya, B.; Nayak, S.P.

doi:10.1107/S1600536810033106

organic compounds

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ISSN: 2056-9890

Volume 66| Part 9| September 2010| Pages o2367-o2368

https://doi.org/10.1107/S1600536810033106

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4-[4-Ethoxycarbonyl-5-(3,4-methylenedioxyphenyl)-3-oxocyclohex-1-en-1-yl]-3-phenylsydnone

Hoong-Kun Fun,^a ^*‡ Wan-Sin Loh,^a § Nithinchandra,^b Balakrishna Kalluraya ^b and Suresh P. Nayak ^b

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and ^bDepartment of Studies in Chemistry, Mangalore University, Mangalagangotri, Mangalore 574 199, India
^*Correspondence e-mail: hkfun@usm.my

(Received 14 August 2010; accepted 17 August 2010; online 21 August 2010)

In the title compound {systematic name: 4-[4-ethoxycarbonyl-5-(3,4-methylenedioxyphenyl)-3-oxocyclohex-1-en-1-yl]-3-phenyl-1,2,3-oxadiazol-3-ium-5-olate}, C₂₄H₂₀N₂O₇, the cyclohexene and dioxole rings adopt envelope conformations. The sydnone ring and the attached phenyl ring form a dihedral angle of 79.0 (1)°. In the molecular structure, a C—H⋯O hydrogen bond generates an S(6) ring and a C—H⋯π interaction involving the phenyl ring is observed. In the crystal structure, molecules are linked into a ribbon-like structure along the a axis by C—H⋯O hydrogen bonds.

Related literature

For general background and applications of sydnone compounds, see: Rai et al. (2008 ); Jyothi et al. (2008 ). For the synthesis of sydnone derivatives, see: Kalluraya et al. (2003 ). For related structures, see: Goh et al. (2010a ,b ,c ). For bond-length data, see: Allen et al. (1987 ). For hydrogen-bond motifs, see: Bernstein et al. (1995 ). For puckering parameters, see: Cremer & Pople (1975 ). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ).

Experimental

Crystal data

C₂₄H₂₀N₂O₇
M_r = 448.42
Triclinic, $[P \overline 1]$
a = 8.8026 (2) Å
b = 11.5133 (2) Å
c = 11.6981 (2) Å
α = 66.860 (1)°
β = 86.545 (1)°
γ = 71.115 (1)°
V = 1028.44 (4) Å³
Z = 2
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 100 K
0.37 × 0.13 × 0.06 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.962, T_max = 0.994
18550 measured reflections
4703 independent reflections
3710 reflections with I > 2σ(I)
R_int = 0.035

Refinement

R[F² > 2σ(F²)] = 0.048
wR(F²) = 0.119
S = 1.03
4703 reflections
299 parameters
H-atom parameters constrained
Δρ_max = 0.56 e Å⁻³
Δρ_min = −0.34 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1–C6 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4A⋯O4ⁱ	0.93	2.49	3.304 (3)	146
C5—H5A⋯O7ⁱⁱ	0.93	2.44	3.258 (2)	146
C14—H14A⋯O6	0.93	2.29	2.998 (2)	133
C10—H10A⋯Cg1	0.97	2.48	3.570 (2)	133
Symmetry codes: (i) x-1, y, z; (ii) -x+1, -y, -z.

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536810033106/ci5156sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810033106/ci5156Isup2.hkl

checkCIF report

Comment top

Sydnones constitute a well defined class of mesoionic compounds that contain the 1,2,3-oxadiazole ring system. The study of sydnones still remains a field of interest because of their electronic structures and also because of the varied types of biological activities displayed by some of them (Rai et al., 2008). Recently sydnone derivatives have been found to exhibit promising antimicrobial properties (Jyothi et al., 2008). The base-catalyzed condensation of 4-acetyl-3-phenyl sydnones with pipernol in aqueous alcoholic medium at 0–50°C gave chalcones. Michael addition of chalcones with ethyl acetoacetate in presence of K₂CO₃, followed by Claisen condensation afforded 3-aryl-4-[6-carbethoxy-5-(3,4-methylenedioxyphenyl)cyclohex-2-en-1-one-3yl] phenylsydnone (Kalluraya et al., 2003).

In the title molecule (Fig.1), the cyclohexene ring (C9–C14) adopts an envelope conformation, with the puckering parameters Q = 0.495 (2) Å, Θ = 55.7 (2)°, φ = 126.6 (3)° (Cremer & Pople, 1975). The dioxole ring also adopts an envelope conformation with atom C19 as the flap. The dihedral angle between the sydnone ring and the attached phenyl ring is 79.0 (1)°. The bond lengths (Allen et al., 1987) and angles are comparable to related structures (Goh et al., 2010a,b,c). An intramolecular C14—H14A···O6 hydrogen bond (Table 1) generates an S(6) ring motif (Fig. 1, Bernstein et al., 1995). An intramolecular C—H···π interaction (Table 1) involving the C1–C6 ring is also observed.

In the crystal packing, intermolecular C4—H4A···O4 and C5—H5A···O7 hydrogen bonds (Table 1) link the molecules into a ribbon-like structure along the a axis (Fig. 2).

Related literature top

For general background and applications of sydnone compounds, see: Rai et al. (2008); Jyothi et al. (2008). For the synthesis of sydnone derivatives, see: Kalluraya et al. (2003). For related structures, see: Goh et al. (2010a,b,c). For bond-length data, see: Allen et al. (1987). For hydrogen-bond motifs, see: Bernstein et al. (1995). For puckering parameters, see: Cremer & Pople (1975). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986).

Experimental top

To a solution of 1-(3-phenylsydnonyl)-3(3,4-methylenedioxyphenyl)-2-propen-1-one (0.01 mol) in dry acetone (50 ml) was added dry potassium carbonate (0.04 mol) and ethyl acetoacetate (0.02 mol) and the mixture was stirred at room temperature overnight and was filtered. The solvent from the filtrate on evaporation gave a solid which was recrystallized from a mixture of ethanol-dioxan. Single crystals suitable for X-ray analysis were obtained from a ethanol solution by slow evaporation.

Structure description top

In the crystal packing, intermolecular C4—H4A···O4 and C5—H5A···O7 hydrogen bonds (Table 1) link the molecules into a ribbon-like structure along the a axis (Fig. 2).

For general background and applications of sydnone compounds, see: Rai et al. (2008); Jyothi et al. (2008). For the synthesis of sydnone derivatives, see: Kalluraya et al. (2003). For related structures, see: Goh et al. (2010a,b,c). For bond-length data, see: Allen et al. (1987). For hydrogen-bond motifs, see: Bernstein et al. (1995). For puckering parameters, see: Cremer & Pople (1975). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986).

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound, showing 50% probability displacement ellipsoids and the atom-numbering scheme. The dashed line indicates a hydrogen bond.
	Fig. 2. The crystal packing of the title compound showing a hydrogen-bonded ribbon, along the a axis. H atoms not involved in hydrogen bonding (dashed lines) have been omitted for clarity.

4-[4-Ethoxycarbonyl-5-(3,4-methylenedioxyphenyl)- 3-oxocyclohex-1-en-1-yl]-3-phenyl-1,2,3-oxadiazol-3-ium-5-olate top

Crystal data top

C₂₄H₂₀N₂O₇	Z = 2
M_r = 448.42	F(000) = 468
Triclinic, P1	D_x = 1.448 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.8026 (2) Å	Cell parameters from 5688 reflections
b = 11.5133 (2) Å	θ = 2.2–30.2°
c = 11.6981 (2) Å	µ = 0.11 mm⁻¹
α = 66.860 (1)°	T = 100 K
β = 86.545 (1)°	Needle, colourless
γ = 71.115 (1)°	0.37 × 0.13 × 0.06 mm
V = 1028.44 (4) Å³

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	4703 independent reflections
Radiation source: fine-focus sealed tube	3710 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.035
φ and ω scans	θ_max = 27.5°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −11→11
T_min = 0.962, T_max = 0.994	k = −14→14
18550 measured reflections	l = −15→15

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.119	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0499P)² + 0.6557P] where P = (F_o² + 2F_c²)/3
4703 reflections	(Δ/σ)_max = 0.001
299 parameters	Δρ_max = 0.56 e Å⁻³
0 restraints	Δρ_min = −0.34 e Å⁻³

Crystal data top

C₂₄H₂₀N₂O₇	γ = 71.115 (1)°
M_r = 448.42	V = 1028.44 (4) Å³
Triclinic, P1	Z = 2
a = 8.8026 (2) Å	Mo Kα radiation
b = 11.5133 (2) Å	µ = 0.11 mm⁻¹
c = 11.6981 (2) Å	T = 100 K
α = 66.860 (1)°	0.37 × 0.13 × 0.06 mm
β = 86.545 (1)°

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	4703 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	3710 reflections with I > 2σ(I)
T_min = 0.962, T_max = 0.994	R_int = 0.035
18550 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	0 restraints
wR(F²) = 0.119	H-atom parameters constrained
S = 1.03	Δρ_max = 0.56 e Å⁻³
4703 reflections	Δρ_min = −0.34 e Å⁻³
299 parameters

Special details top

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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
O1	0.54796 (15)	−0.47982 (12)	0.24568 (11)	0.0225 (3)
O2	0.09931 (15)	0.43102 (12)	0.42387 (11)	0.0228 (3)
O3	0.34786 (15)	0.29504 (13)	0.53026 (11)	0.0244 (3)
O4	0.73361 (16)	0.19987 (13)	0.20782 (12)	0.0263 (3)
O5	0.63381 (15)	0.31720 (12)	0.00796 (11)	0.0234 (3)
O6	0.73888 (15)	−0.39479 (12)	0.14030 (12)	0.0249 (3)
O7	0.79429 (16)	0.03513 (13)	0.01666 (12)	0.0271 (3)
N1	0.39657 (17)	−0.31654 (14)	0.28604 (13)	0.0175 (3)
N2	0.41071 (19)	−0.43911 (14)	0.30166 (14)	0.0227 (3)
C1	0.2822 (2)	−0.29087 (18)	0.47181 (16)	0.0219 (4)
H1A	0.3768	−0.3542	0.5175	0.026*
C2	0.1577 (2)	−0.23095 (19)	0.52984 (17)	0.0255 (4)
H2A	0.1680	−0.2536	0.6152	0.031*
C3	0.0177 (2)	−0.13688 (19)	0.45938 (19)	0.0279 (4)
H3A	−0.0658	−0.0963	0.4980	0.033*
C4	0.0010 (2)	−0.10279 (19)	0.33208 (18)	0.0277 (4)
H4A	−0.0935	−0.0395	0.2861	0.033*
C5	0.1236 (2)	−0.16201 (18)	0.27268 (16)	0.0231 (4)
H5A	0.1129	−0.1404	0.1875	0.028*
C6	0.2628 (2)	−0.25450 (16)	0.34455 (15)	0.0181 (3)
C7	0.6164 (2)	−0.37744 (16)	0.19344 (15)	0.0186 (4)
C8	0.5132 (2)	−0.26951 (16)	0.22242 (15)	0.0165 (3)
C9	0.5348 (2)	−0.14190 (16)	0.19358 (14)	0.0155 (3)
C10	0.4237 (2)	−0.03949 (16)	0.23803 (15)	0.0161 (3)
H10A	0.3924	−0.0853	0.3202	0.019*
H10B	0.3269	0.0099	0.1819	0.019*
C11	0.5027 (2)	0.05872 (17)	0.24418 (16)	0.0196 (4)
H11A	0.5949	0.0075	0.3064	0.023*
C12	0.5672 (2)	0.12241 (17)	0.11849 (16)	0.0209 (4)
H12A	0.4763	0.1728	0.0550	0.025*
C13	0.6849 (2)	0.01333 (18)	0.08194 (16)	0.0200 (4)
C14	0.6583 (2)	−0.11497 (17)	0.12458 (15)	0.0177 (3)
H14A	0.7294	−0.1819	0.1035	0.021*
C15	0.3878 (2)	0.16253 (17)	0.28630 (16)	0.0193 (4)
C16	0.2380 (2)	0.24512 (18)	0.22215 (16)	0.0225 (4)
H16A	0.2090	0.2370	0.1512	0.027*
C17	0.1295 (2)	0.34015 (17)	0.26119 (16)	0.0212 (4)
H17A	0.0298	0.3947	0.2183	0.025*
C18	0.1795 (2)	0.34732 (16)	0.36599 (15)	0.0180 (4)
C19	0.1948 (2)	0.38560 (18)	0.53747 (17)	0.0232 (4)
H19A	0.1418	0.3407	0.6080	0.028*
H19B	0.2093	0.4608	0.5482	0.028*
C20	0.3280 (2)	0.26646 (17)	0.42936 (16)	0.0190 (4)
C21	0.4350 (2)	0.17364 (17)	0.39255 (16)	0.0193 (4)
H21A	0.5346	0.1204	0.4362	0.023*
C22	0.6534 (2)	0.21628 (17)	0.11888 (16)	0.0187 (4)
C23	0.7312 (2)	0.40341 (18)	−0.00653 (18)	0.0267 (4)
H23A	0.7349	0.4177	0.0695	0.032*
H23B	0.6825	0.4896	−0.0740	0.032*
C24	0.8997 (2)	0.3393 (2)	−0.0344 (2)	0.0348 (5)
H24A	0.9649	0.3929	−0.0374	0.052*
H24B	0.8965	0.3325	−0.1134	0.052*
H24C	0.9450	0.2516	0.0298	0.052*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0288 (7)	0.0144 (6)	0.0231 (6)	−0.0049 (5)	0.0041 (5)	−0.0082 (5)
O2	0.0216 (6)	0.0217 (6)	0.0233 (6)	0.0021 (5)	0.0006 (5)	−0.0142 (5)
O3	0.0209 (7)	0.0281 (7)	0.0225 (6)	0.0006 (5)	−0.0002 (5)	−0.0150 (5)
O4	0.0303 (7)	0.0250 (7)	0.0251 (7)	−0.0094 (6)	0.0006 (5)	−0.0109 (5)
O5	0.0281 (7)	0.0187 (6)	0.0231 (6)	−0.0081 (5)	0.0003 (5)	−0.0076 (5)
O6	0.0263 (7)	0.0211 (7)	0.0299 (7)	−0.0048 (5)	0.0064 (5)	−0.0158 (5)
O7	0.0295 (7)	0.0278 (7)	0.0315 (7)	−0.0141 (6)	0.0156 (6)	−0.0175 (6)
N1	0.0233 (8)	0.0134 (7)	0.0153 (7)	−0.0058 (6)	0.0011 (5)	−0.0052 (5)
N2	0.0304 (9)	0.0148 (7)	0.0217 (7)	−0.0066 (6)	0.0047 (6)	−0.0069 (6)
C1	0.0248 (9)	0.0215 (9)	0.0191 (8)	−0.0096 (7)	0.0013 (7)	−0.0061 (7)
C2	0.0312 (10)	0.0313 (10)	0.0212 (9)	−0.0166 (9)	0.0083 (7)	−0.0134 (8)
C3	0.0280 (10)	0.0265 (10)	0.0360 (11)	−0.0117 (8)	0.0134 (8)	−0.0185 (8)
C4	0.0237 (10)	0.0201 (9)	0.0345 (10)	−0.0037 (8)	0.0019 (8)	−0.0087 (8)
C5	0.0281 (10)	0.0198 (9)	0.0193 (8)	−0.0082 (8)	0.0008 (7)	−0.0053 (7)
C6	0.0221 (9)	0.0152 (8)	0.0200 (8)	−0.0087 (7)	0.0053 (7)	−0.0085 (6)
C7	0.0246 (9)	0.0138 (8)	0.0166 (8)	−0.0040 (7)	−0.0021 (7)	−0.0062 (6)
C8	0.0190 (8)	0.0156 (8)	0.0150 (8)	−0.0039 (7)	0.0010 (6)	−0.0074 (6)
C9	0.0185 (8)	0.0149 (8)	0.0125 (7)	−0.0032 (6)	−0.0018 (6)	−0.0062 (6)
C10	0.0179 (8)	0.0141 (8)	0.0167 (8)	−0.0044 (6)	0.0029 (6)	−0.0073 (6)
C11	0.0216 (9)	0.0179 (8)	0.0210 (8)	−0.0062 (7)	0.0035 (7)	−0.0099 (7)
C12	0.0238 (9)	0.0194 (9)	0.0214 (9)	−0.0073 (7)	0.0028 (7)	−0.0101 (7)
C13	0.0225 (9)	0.0232 (9)	0.0188 (8)	−0.0086 (7)	0.0044 (7)	−0.0122 (7)
C14	0.0200 (8)	0.0175 (8)	0.0172 (8)	−0.0032 (7)	0.0023 (6)	−0.0109 (6)
C15	0.0199 (9)	0.0152 (8)	0.0237 (9)	−0.0068 (7)	0.0083 (7)	−0.0086 (7)
C16	0.0287 (10)	0.0235 (9)	0.0203 (8)	−0.0105 (8)	0.0051 (7)	−0.0127 (7)
C17	0.0220 (9)	0.0183 (9)	0.0211 (9)	−0.0046 (7)	0.0013 (7)	−0.0070 (7)
C18	0.0199 (9)	0.0129 (8)	0.0207 (8)	−0.0036 (7)	0.0070 (7)	−0.0081 (6)
C19	0.0234 (9)	0.0227 (9)	0.0235 (9)	−0.0024 (7)	0.0021 (7)	−0.0132 (7)
C20	0.0212 (9)	0.0164 (8)	0.0195 (8)	−0.0063 (7)	0.0043 (7)	−0.0075 (6)
C21	0.0179 (8)	0.0151 (8)	0.0225 (9)	−0.0033 (7)	0.0041 (7)	−0.0071 (7)
C22	0.0187 (8)	0.0175 (8)	0.0210 (8)	−0.0038 (7)	0.0051 (7)	−0.0108 (7)
C23	0.0346 (11)	0.0187 (9)	0.0287 (10)	−0.0136 (8)	0.0014 (8)	−0.0071 (7)
C24	0.0315 (11)	0.0345 (12)	0.0395 (12)	−0.0176 (9)	0.0060 (9)	−0.0107 (9)

Geometric parameters (Å, º) top

O1—N2	1.3739 (19)	C10—C11	1.532 (2)
O1—C7	1.405 (2)	C10—H10A	0.97
O2—C18	1.379 (2)	C10—H10B	0.97
O2—C19	1.432 (2)	C11—C15	1.521 (2)
O3—C20	1.378 (2)	C11—C12	1.531 (2)
O3—C19	1.434 (2)	C11—H11A	0.98
O4—C22	1.210 (2)	C12—C22	1.509 (2)
O5—C22	1.333 (2)	C12—C13	1.536 (2)
O5—C23	1.466 (2)	C12—H12A	0.98
O6—C7	1.211 (2)	C13—C14	1.455 (2)
O7—C13	1.221 (2)	C14—H14A	0.93
N1—N2	1.314 (2)	C15—C16	1.397 (3)
N1—C8	1.361 (2)	C15—C21	1.399 (2)
N1—C6	1.452 (2)	C16—C17	1.408 (2)
C1—C6	1.384 (2)	C16—H16A	0.93
C1—C2	1.388 (3)	C17—C18	1.368 (2)
C1—H1A	0.93	C17—H17A	0.93
C2—C3	1.389 (3)	C18—C20	1.383 (2)
C2—H2A	0.93	C19—H19A	0.97
C3—C4	1.387 (3)	C19—H19B	0.97
C3—H3A	0.93	C20—C21	1.370 (2)
C4—C5	1.385 (3)	C21—H21A	0.93
C4—H4A	0.93	C23—C24	1.508 (3)
C5—C6	1.385 (2)	C23—H23A	0.97
C5—H5A	0.9300	C23—H23B	0.97
C7—C8	1.431 (2)	C24—H24A	0.96
C8—C9	1.446 (2)	C24—H24B	0.96
C9—C14	1.358 (2)	C24—H24C	0.96
C9—C10	1.514 (2)

N2—O1—C7	110.82 (12)	C11—C12—C13	110.07 (14)
C18—O2—C19	105.46 (13)	C22—C12—H12A	108.5
C20—O3—C19	105.33 (13)	C11—C12—H12A	108.5
C22—O5—C23	115.58 (14)	C13—C12—H12A	108.5
N2—N1—C8	115.22 (14)	O7—C13—C14	121.36 (16)
N2—N1—C6	114.75 (14)	O7—C13—C12	120.91 (16)
C8—N1—C6	129.96 (14)	C14—C13—C12	117.71 (15)
N1—N2—O1	104.74 (13)	C9—C14—C13	123.30 (16)
C6—C1—C2	118.67 (17)	C9—C14—H14A	118.4
C6—C1—H1A	120.7	C13—C14—H14A	118.4
C2—C1—H1A	120.7	C16—C15—C21	119.99 (16)
C1—C2—C3	119.48 (17)	C16—C15—C11	121.71 (16)
C1—C2—H2A	120.3	C21—C15—C11	118.30 (15)
C3—C2—H2A	120.3	C15—C16—C17	122.31 (16)
C4—C3—C2	120.67 (18)	C15—C16—H16A	118.8
C4—C3—H3A	119.7	C17—C16—H16A	118.8
C2—C3—H3A	119.7	C18—C17—C16	115.96 (16)
C5—C4—C3	120.66 (18)	C18—C17—H17A	122.0
C5—C4—H4A	119.7	C16—C17—H17A	122.0
C3—C4—H4A	119.7	C17—C18—O2	128.32 (16)
C6—C5—C4	117.67 (17)	C17—C18—C20	121.97 (16)
C6—C5—H5A	121.2	O2—C18—C20	109.71 (15)
C4—C5—H5A	121.2	O2—C19—O3	107.89 (13)
C1—C6—C5	122.84 (16)	O2—C19—H19A	110.1
C1—C6—N1	117.38 (15)	O3—C19—H19A	110.1
C5—C6—N1	119.77 (15)	O2—C19—H19B	110.1
O6—C7—O1	120.52 (15)	O3—C19—H19B	110.1
O6—C7—C8	134.77 (16)	H19A—C19—H19B	108.4
O1—C7—C8	104.70 (14)	C21—C20—O3	127.31 (16)
N1—C8—C7	104.51 (14)	C21—C20—C18	122.79 (16)
N1—C8—C9	128.77 (15)	O3—C20—C18	109.90 (15)
C7—C8—C9	126.68 (15)	C20—C21—C15	116.97 (16)
C14—C9—C8	118.32 (15)	C20—C21—H21A	121.5
C14—C9—C10	120.05 (15)	C15—C21—H21A	121.5
C8—C9—C10	121.62 (14)	O4—C22—O5	124.34 (16)
C9—C10—C11	112.31 (14)	O4—C22—C12	124.18 (16)
C9—C10—H10A	109.1	O5—C22—C12	111.46 (14)
C11—C10—H10A	109.1	O5—C23—C24	109.97 (15)
C9—C10—H10B	109.1	O5—C23—H23A	109.7
C11—C10—H10B	109.1	C24—C23—H23A	109.7
H10A—C10—H10B	107.9	O5—C23—H23B	109.7
C15—C11—C12	112.34 (14)	C24—C23—H23B	109.7
C15—C11—C10	111.42 (14)	H23A—C23—H23B	108.2
C12—C11—C10	109.94 (14)	C23—C24—H24A	109.5
C15—C11—H11A	107.6	C23—C24—H24B	109.5
C12—C11—H11A	107.6	H24A—C24—H24B	109.5
C10—C11—H11A	107.6	C23—C24—H24C	109.5
C22—C12—C11	113.06 (14)	H24A—C24—H24C	109.5
C22—C12—C13	108.19 (14)	H24B—C24—H24C	109.5

C8—N1—N2—O1	0.58 (18)	C11—C12—C13—O7	−151.39 (16)
C6—N1—N2—O1	−176.69 (13)	C22—C12—C13—C14	154.41 (15)
C7—O1—N2—N1	−0.90 (17)	C11—C12—C13—C14	30.4 (2)
C6—C1—C2—C3	0.1 (3)	C8—C9—C14—C13	175.29 (15)
C1—C2—C3—C4	0.2 (3)	C10—C9—C14—C13	−4.6 (2)
C2—C3—C4—C5	0.1 (3)	O7—C13—C14—C9	−177.63 (16)
C3—C4—C5—C6	−0.7 (3)	C12—C13—C14—C9	0.5 (2)
C2—C1—C6—C5	−0.8 (3)	C12—C11—C15—C16	66.7 (2)
C2—C1—C6—N1	178.54 (15)	C10—C11—C15—C16	−57.2 (2)
C4—C5—C6—C1	1.1 (3)	C12—C11—C15—C21	−113.64 (17)
C4—C5—C6—N1	−178.24 (15)	C10—C11—C15—C21	122.49 (16)
N2—N1—C6—C1	78.33 (19)	C21—C15—C16—C17	−0.7 (3)
C8—N1—C6—C1	−98.4 (2)	C11—C15—C16—C17	178.99 (16)
N2—N1—C6—C5	−102.29 (18)	C15—C16—C17—C18	0.2 (3)
C8—N1—C6—C5	80.9 (2)	C16—C17—C18—O2	179.39 (16)
N2—O1—C7—O6	179.69 (15)	C16—C17—C18—C20	0.3 (3)
N2—O1—C7—C8	0.88 (17)	C19—O2—C18—C17	172.59 (18)
N2—N1—C8—C7	−0.05 (19)	C19—O2—C18—C20	−8.19 (18)
C6—N1—C8—C7	176.72 (15)	C18—O2—C19—O3	12.89 (18)
N2—N1—C8—C9	−177.79 (16)	C20—O3—C19—O2	−12.72 (18)
C6—N1—C8—C9	−1.0 (3)	C19—O3—C20—C21	−172.51 (17)
O6—C7—C8—N1	−179.06 (19)	C19—O3—C20—C18	7.75 (18)
O1—C7—C8—N1	−0.50 (17)	C17—C18—C20—C21	−0.2 (3)
O6—C7—C8—C9	−1.3 (3)	O2—C18—C20—C21	−179.48 (15)
O1—C7—C8—C9	177.31 (15)	C17—C18—C20—O3	179.55 (15)
N1—C8—C9—C14	−177.80 (16)	O2—C18—C20—O3	0.27 (19)
C7—C8—C9—C14	4.9 (3)	O3—C20—C21—C15	180.00 (16)
N1—C8—C9—C10	2.0 (3)	C18—C20—C21—C15	−0.3 (3)
C7—C8—C9—C10	−175.23 (15)	C16—C15—C21—C20	0.7 (2)
C14—C9—C10—C11	−23.1 (2)	C11—C15—C21—C20	−178.98 (15)
C8—C9—C10—C11	157.03 (15)	C23—O5—C22—O4	6.4 (2)
C9—C10—C11—C15	178.75 (14)	C23—O5—C22—C12	−171.70 (14)
C9—C10—C11—C12	53.54 (18)	C11—C12—C22—O4	34.7 (2)
C15—C11—C12—C22	57.8 (2)	C13—C12—C22—O4	−87.5 (2)
C10—C11—C12—C22	−177.53 (14)	C11—C12—C22—O5	−147.17 (15)
C15—C11—C12—C13	178.89 (14)	C13—C12—C22—O5	90.67 (17)
C10—C11—C12—C13	−56.42 (18)	C22—O5—C23—C24	80.80 (19)
C22—C12—C13—O7	−27.4 (2)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C1–C6 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4A···O4ⁱ	0.93	2.49	3.304 (3)	146
C5—H5A···O7ⁱⁱ	0.93	2.44	3.258 (2)	146
C14—H14A···O6	0.93	2.29	2.998 (2)	133
C10—H10A···Cg1	0.97	2.48	3.570 (2)	133

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

Experimental details

Crystal data
Chemical formula	C₂₄H₂₀N₂O₇
M_r	448.42
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	8.8026 (2), 11.5133 (2), 11.6981 (2)
α, β, γ (°)	66.860 (1), 86.545 (1), 71.115 (1)
V (Å³)	1028.44 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.37 × 0.13 × 0.06

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.962, 0.994
No. of measured, independent and observed [I > 2σ(I)] reflections	18550, 4703, 3710
R_int	0.035
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.119, 1.03
No. of reflections	4703
No. of parameters	299
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.56, −0.34

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C1–C6 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4A···O4ⁱ	0.93	2.49	3.304 (3)	146
C5—H5A···O7ⁱⁱ	0.93	2.44	3.258 (2)	146
C14—H14A···O6	0.93	2.29	2.998 (2)	133
C10—H10A···Cg1	0.97	2.48	3.570 (2)	133

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

Footnotes

‡Thomson Reuters ResearcherID: A-3561-2009.

§Thomson Reuters ResearcherID: C-7581-2009

Acknowledgements

The authors thank Universiti Sains Malaysia (USM) for the Research University Golden Goose Grant (1001/PFIZIK/811012). WSL thanks the Malaysian Government and USM for the award of a research fellowship.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CSD CrossRef Web of Science 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 (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105–107. CrossRef CAS Web of Science IUCr Journals Google Scholar
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358. CrossRef CAS Web of Science Google Scholar
Goh, J. H., Fun, H.-K., Nithinchandra, & Kalluraya, B. (2010a). Acta Cryst. E66, o1303. Google Scholar
Goh, J. H., Fun, H.-K., Nithinchandra, & Kalluraya, B. (2010b). Acta Cryst. E66, o1394–o1395. Google Scholar
Goh, J. H., Fun, H.-K., Nithinchandra, & Kalluraya, B. (2010c). Acta Cryst. E66, o2198–o2199. Google Scholar
Jyothi, C. H., Girisha, K. S., Adithya, A. & Kalluraya, B. (2008). Eur. J. Med. Chem. 43, 2831–2834. Web of Science PubMed Google Scholar
Kalluraya, B. & Rahiman, A. M. (2003). Indian J. Chem. Sect. B, 42, 1141–1148. Google Scholar
Rai, N. S., Kalluraya, B., Lingappa, B., Shenoy, S. & Puranic, V. G. (2008). Eur. J. Med. Chem. 43, 1715–1720. Web of Science PubMed 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

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Volume 66| Part 9| September 2010| Pages o2367-o2368

https://doi.org/10.1107/S1600536810033106

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

4-[4-Eth­­oxy­carbonyl-5-(3,4-methyl­ene­di­oxy­phen­yl)-3-oxo­cyclo­hex-1-en-1-yl]-3-phenyl­sydnone

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Experimental

Crystal data

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References

organic compounds

4-[4-Ethoxycarbonyl-5-(3,4-methylenedioxyphenyl)-3-oxocyclohex-1-en-1-yl]-3-phenylsydnone