Literature DB >> 21588708

4-[4-Eth-oxy-carbonyl-5-(3,4-methyl-ene-dioxy-phen-yl)-3-oxocyclo-hex-1-en-1-yl]-3-phenyl-sydnone.

Hoong-Kun Fun, Wan-Sin Loh, Balakrishna Kalluraya, Suresh P Nayak.   

Abstract

In the title compound {systematic name: 4-[4-eth-oxy-carbonyl-5-(3,4-methyl-ene-dioxy-phen-yl)-3-oxocyclo-hex-1-en-1-yl]-3-phenyl-1,2,3-oxadiazol-3-ium-5-olate}, C(24)H(20)N(2)O(7), the cyclo-hexene and dioxole rings adopt envelope conformations. The sydnone ring and the attached phenyl ring form a dihedral angle of 79.0 (1)°. In the mol-ecular structure, a C-H⋯O hydrogen bond generates an S(6) ring and a C-H⋯π inter-action involving the phenyl ring is observed. In the crystal structure, mol-ecules are linked into a ribbon-like structure along the a axis by C-H⋯O hydrogen bonds.

Entities:  

Year:  2010        PMID: 21588708      PMCID: PMC3008016          DOI: 10.1107/S1600536810033106

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN: 1600-5368


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. (2010 ▶). 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 = 448.42 Triclinic, 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[F 2 > 2σ(F 2)] = 0.048 wR(F 2) = 0.119 S = 1.03 4703 reflections 299 parameters H-atom parameters constrained Δρmax = 0.56 e Å−3 Δρmin = −0.34 e Å−3 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 ▶). Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810033106/ci5156sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536810033106/ci5156Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C24H20N2O7Z = 2
Mr = 448.42F(000) = 468
Triclinic, P1Dx = 1.448 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.8026 (2) ÅCell parameters from 5688 reflections
b = 11.5133 (2) Åθ = 2.2–30.2°
c = 11.6981 (2) ŵ = 0.11 mm1
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
Bruker SMART APEXII CCD area-detector diffractometer4703 independent reflections
Radiation source: fine-focus sealed tube3710 reflections with I > 2σ(I)
graphiteRint = 0.035
φ and ω scansθmax = 27.5°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2009)h = −11→11
Tmin = 0.962, Tmax = 0.994k = −14→14
18550 measured reflectionsl = −15→15
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.048Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.119H-atom parameters constrained
S = 1.03w = 1/[σ2(Fo2) + (0.0499P)2 + 0.6557P] where P = (Fo2 + 2Fc2)/3
4703 reflections(Δ/σ)max = 0.001
299 parametersΔρmax = 0.56 e Å3
0 restraintsΔρmin = −0.34 e Å3
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.
xyzUiso*/Ueq
O10.54796 (15)−0.47982 (12)0.24568 (11)0.0225 (3)
O20.09931 (15)0.43102 (12)0.42387 (11)0.0228 (3)
O30.34786 (15)0.29504 (13)0.53026 (11)0.0244 (3)
O40.73361 (16)0.19987 (13)0.20782 (12)0.0263 (3)
O50.63381 (15)0.31720 (12)0.00796 (11)0.0234 (3)
O60.73888 (15)−0.39479 (12)0.14030 (12)0.0249 (3)
O70.79429 (16)0.03513 (13)0.01666 (12)0.0271 (3)
N10.39657 (17)−0.31654 (14)0.28604 (13)0.0175 (3)
N20.41071 (19)−0.43911 (14)0.30166 (14)0.0227 (3)
C10.2822 (2)−0.29087 (18)0.47181 (16)0.0219 (4)
H1A0.3768−0.35420.51750.026*
C20.1577 (2)−0.23095 (19)0.52984 (17)0.0255 (4)
H2A0.1680−0.25360.61520.031*
C30.0177 (2)−0.13688 (19)0.45938 (19)0.0279 (4)
H3A−0.0658−0.09630.49800.033*
C40.0010 (2)−0.10279 (19)0.33208 (18)0.0277 (4)
H4A−0.0935−0.03950.28610.033*
C50.1236 (2)−0.16201 (18)0.27268 (16)0.0231 (4)
H5A0.1129−0.14040.18750.028*
C60.2628 (2)−0.25450 (16)0.34455 (15)0.0181 (3)
C70.6164 (2)−0.37744 (16)0.19344 (15)0.0186 (4)
C80.5132 (2)−0.26951 (16)0.22242 (15)0.0165 (3)
C90.5348 (2)−0.14190 (16)0.19358 (14)0.0155 (3)
C100.4237 (2)−0.03949 (16)0.23803 (15)0.0161 (3)
H10A0.3924−0.08530.32020.019*
H10B0.32690.00990.18190.019*
C110.5027 (2)0.05872 (17)0.24418 (16)0.0196 (4)
H11A0.59490.00750.30640.023*
C120.5672 (2)0.12241 (17)0.11849 (16)0.0209 (4)
H12A0.47630.17280.05500.025*
C130.6849 (2)0.01333 (18)0.08194 (16)0.0200 (4)
C140.6583 (2)−0.11497 (17)0.12458 (15)0.0177 (3)
H14A0.7294−0.18190.10350.021*
C150.3878 (2)0.16253 (17)0.28630 (16)0.0193 (4)
C160.2380 (2)0.24512 (18)0.22215 (16)0.0225 (4)
H16A0.20900.23700.15120.027*
C170.1295 (2)0.34015 (17)0.26119 (16)0.0212 (4)
H17A0.02980.39470.21830.025*
C180.1795 (2)0.34732 (16)0.36599 (15)0.0180 (4)
C190.1948 (2)0.38560 (18)0.53747 (17)0.0232 (4)
H19A0.14180.34070.60800.028*
H19B0.20930.46080.54820.028*
C200.3280 (2)0.26646 (17)0.42936 (16)0.0190 (4)
C210.4350 (2)0.17364 (17)0.39255 (16)0.0193 (4)
H21A0.53460.12040.43620.023*
C220.6534 (2)0.21628 (17)0.11888 (16)0.0187 (4)
C230.7312 (2)0.40341 (18)−0.00653 (18)0.0267 (4)
H23A0.73490.41770.06950.032*
H23B0.68250.4896−0.07400.032*
C240.8997 (2)0.3393 (2)−0.0344 (2)0.0348 (5)
H24A0.96490.3929−0.03740.052*
H24B0.89650.3325−0.11340.052*
H24C0.94500.25160.02980.052*
U11U22U33U12U13U23
O10.0288 (7)0.0144 (6)0.0231 (6)−0.0049 (5)0.0041 (5)−0.0082 (5)
O20.0216 (6)0.0217 (6)0.0233 (6)0.0021 (5)0.0006 (5)−0.0142 (5)
O30.0209 (7)0.0281 (7)0.0225 (6)0.0006 (5)−0.0002 (5)−0.0150 (5)
O40.0303 (7)0.0250 (7)0.0251 (7)−0.0094 (6)0.0006 (5)−0.0109 (5)
O50.0281 (7)0.0187 (6)0.0231 (6)−0.0081 (5)0.0003 (5)−0.0076 (5)
O60.0263 (7)0.0211 (7)0.0299 (7)−0.0048 (5)0.0064 (5)−0.0158 (5)
O70.0295 (7)0.0278 (7)0.0315 (7)−0.0141 (6)0.0156 (6)−0.0175 (6)
N10.0233 (8)0.0134 (7)0.0153 (7)−0.0058 (6)0.0011 (5)−0.0052 (5)
N20.0304 (9)0.0148 (7)0.0217 (7)−0.0066 (6)0.0047 (6)−0.0069 (6)
C10.0248 (9)0.0215 (9)0.0191 (8)−0.0096 (7)0.0013 (7)−0.0061 (7)
C20.0312 (10)0.0313 (10)0.0212 (9)−0.0166 (9)0.0083 (7)−0.0134 (8)
C30.0280 (10)0.0265 (10)0.0360 (11)−0.0117 (8)0.0134 (8)−0.0185 (8)
C40.0237 (10)0.0201 (9)0.0345 (10)−0.0037 (8)0.0019 (8)−0.0087 (8)
C50.0281 (10)0.0198 (9)0.0193 (8)−0.0082 (8)0.0008 (7)−0.0053 (7)
C60.0221 (9)0.0152 (8)0.0200 (8)−0.0087 (7)0.0053 (7)−0.0085 (6)
C70.0246 (9)0.0138 (8)0.0166 (8)−0.0040 (7)−0.0021 (7)−0.0062 (6)
C80.0190 (8)0.0156 (8)0.0150 (8)−0.0039 (7)0.0010 (6)−0.0074 (6)
C90.0185 (8)0.0149 (8)0.0125 (7)−0.0032 (6)−0.0018 (6)−0.0062 (6)
C100.0179 (8)0.0141 (8)0.0167 (8)−0.0044 (6)0.0029 (6)−0.0073 (6)
C110.0216 (9)0.0179 (8)0.0210 (8)−0.0062 (7)0.0035 (7)−0.0099 (7)
C120.0238 (9)0.0194 (9)0.0214 (9)−0.0073 (7)0.0028 (7)−0.0101 (7)
C130.0225 (9)0.0232 (9)0.0188 (8)−0.0086 (7)0.0044 (7)−0.0122 (7)
C140.0200 (8)0.0175 (8)0.0172 (8)−0.0032 (7)0.0023 (6)−0.0109 (6)
C150.0199 (9)0.0152 (8)0.0237 (9)−0.0068 (7)0.0083 (7)−0.0086 (7)
C160.0287 (10)0.0235 (9)0.0203 (8)−0.0105 (8)0.0051 (7)−0.0127 (7)
C170.0220 (9)0.0183 (9)0.0211 (9)−0.0046 (7)0.0013 (7)−0.0070 (7)
C180.0199 (9)0.0129 (8)0.0207 (8)−0.0036 (7)0.0070 (7)−0.0081 (6)
C190.0234 (9)0.0227 (9)0.0235 (9)−0.0024 (7)0.0021 (7)−0.0132 (7)
C200.0212 (9)0.0164 (8)0.0195 (8)−0.0063 (7)0.0043 (7)−0.0075 (6)
C210.0179 (8)0.0151 (8)0.0225 (9)−0.0033 (7)0.0041 (7)−0.0071 (7)
C220.0187 (8)0.0175 (8)0.0210 (8)−0.0038 (7)0.0051 (7)−0.0108 (7)
C230.0346 (11)0.0187 (9)0.0287 (10)−0.0136 (8)0.0014 (8)−0.0071 (7)
C240.0315 (11)0.0345 (12)0.0395 (12)−0.0176 (9)0.0060 (9)−0.0107 (9)
O1—N21.3739 (19)C10—C111.532 (2)
O1—C71.405 (2)C10—H10A0.97
O2—C181.379 (2)C10—H10B0.97
O2—C191.432 (2)C11—C151.521 (2)
O3—C201.378 (2)C11—C121.531 (2)
O3—C191.434 (2)C11—H11A0.98
O4—C221.210 (2)C12—C221.509 (2)
O5—C221.333 (2)C12—C131.536 (2)
O5—C231.466 (2)C12—H12A0.98
O6—C71.211 (2)C13—C141.455 (2)
O7—C131.221 (2)C14—H14A0.93
N1—N21.314 (2)C15—C161.397 (3)
N1—C81.361 (2)C15—C211.399 (2)
N1—C61.452 (2)C16—C171.408 (2)
C1—C61.384 (2)C16—H16A0.93
C1—C21.388 (3)C17—C181.368 (2)
C1—H1A0.93C17—H17A0.93
C2—C31.389 (3)C18—C201.383 (2)
C2—H2A0.93C19—H19A0.97
C3—C41.387 (3)C19—H19B0.97
C3—H3A0.93C20—C211.370 (2)
C4—C51.385 (3)C21—H21A0.93
C4—H4A0.93C23—C241.508 (3)
C5—C61.385 (2)C23—H23A0.97
C5—H5A0.9300C23—H23B0.97
C7—C81.431 (2)C24—H24A0.96
C8—C91.446 (2)C24—H24B0.96
C9—C141.358 (2)C24—H24C0.96
C9—C101.514 (2)
N2—O1—C7110.82 (12)C11—C12—C13110.07 (14)
C18—O2—C19105.46 (13)C22—C12—H12A108.5
C20—O3—C19105.33 (13)C11—C12—H12A108.5
C22—O5—C23115.58 (14)C13—C12—H12A108.5
N2—N1—C8115.22 (14)O7—C13—C14121.36 (16)
N2—N1—C6114.75 (14)O7—C13—C12120.91 (16)
C8—N1—C6129.96 (14)C14—C13—C12117.71 (15)
N1—N2—O1104.74 (13)C9—C14—C13123.30 (16)
C6—C1—C2118.67 (17)C9—C14—H14A118.4
C6—C1—H1A120.7C13—C14—H14A118.4
C2—C1—H1A120.7C16—C15—C21119.99 (16)
C1—C2—C3119.48 (17)C16—C15—C11121.71 (16)
C1—C2—H2A120.3C21—C15—C11118.30 (15)
C3—C2—H2A120.3C15—C16—C17122.31 (16)
C4—C3—C2120.67 (18)C15—C16—H16A118.8
C4—C3—H3A119.7C17—C16—H16A118.8
C2—C3—H3A119.7C18—C17—C16115.96 (16)
C5—C4—C3120.66 (18)C18—C17—H17A122.0
C5—C4—H4A119.7C16—C17—H17A122.0
C3—C4—H4A119.7C17—C18—O2128.32 (16)
C6—C5—C4117.67 (17)C17—C18—C20121.97 (16)
C6—C5—H5A121.2O2—C18—C20109.71 (15)
C4—C5—H5A121.2O2—C19—O3107.89 (13)
C1—C6—C5122.84 (16)O2—C19—H19A110.1
C1—C6—N1117.38 (15)O3—C19—H19A110.1
C5—C6—N1119.77 (15)O2—C19—H19B110.1
O6—C7—O1120.52 (15)O3—C19—H19B110.1
O6—C7—C8134.77 (16)H19A—C19—H19B108.4
O1—C7—C8104.70 (14)C21—C20—O3127.31 (16)
N1—C8—C7104.51 (14)C21—C20—C18122.79 (16)
N1—C8—C9128.77 (15)O3—C20—C18109.90 (15)
C7—C8—C9126.68 (15)C20—C21—C15116.97 (16)
C14—C9—C8118.32 (15)C20—C21—H21A121.5
C14—C9—C10120.05 (15)C15—C21—H21A121.5
C8—C9—C10121.62 (14)O4—C22—O5124.34 (16)
C9—C10—C11112.31 (14)O4—C22—C12124.18 (16)
C9—C10—H10A109.1O5—C22—C12111.46 (14)
C11—C10—H10A109.1O5—C23—C24109.97 (15)
C9—C10—H10B109.1O5—C23—H23A109.7
C11—C10—H10B109.1C24—C23—H23A109.7
H10A—C10—H10B107.9O5—C23—H23B109.7
C15—C11—C12112.34 (14)C24—C23—H23B109.7
C15—C11—C10111.42 (14)H23A—C23—H23B108.2
C12—C11—C10109.94 (14)C23—C24—H24A109.5
C15—C11—H11A107.6C23—C24—H24B109.5
C12—C11—H11A107.6H24A—C24—H24B109.5
C10—C11—H11A107.6C23—C24—H24C109.5
C22—C12—C11113.06 (14)H24A—C24—H24C109.5
C22—C12—C13108.19 (14)H24B—C24—H24C109.5
C8—N1—N2—O10.58 (18)C11—C12—C13—O7−151.39 (16)
C6—N1—N2—O1−176.69 (13)C22—C12—C13—C14154.41 (15)
C7—O1—N2—N1−0.90 (17)C11—C12—C13—C1430.4 (2)
C6—C1—C2—C30.1 (3)C8—C9—C14—C13175.29 (15)
C1—C2—C3—C40.2 (3)C10—C9—C14—C13−4.6 (2)
C2—C3—C4—C50.1 (3)O7—C13—C14—C9−177.63 (16)
C3—C4—C5—C6−0.7 (3)C12—C13—C14—C90.5 (2)
C2—C1—C6—C5−0.8 (3)C12—C11—C15—C1666.7 (2)
C2—C1—C6—N1178.54 (15)C10—C11—C15—C16−57.2 (2)
C4—C5—C6—C11.1 (3)C12—C11—C15—C21−113.64 (17)
C4—C5—C6—N1−178.24 (15)C10—C11—C15—C21122.49 (16)
N2—N1—C6—C178.33 (19)C21—C15—C16—C17−0.7 (3)
C8—N1—C6—C1−98.4 (2)C11—C15—C16—C17178.99 (16)
N2—N1—C6—C5−102.29 (18)C15—C16—C17—C180.2 (3)
C8—N1—C6—C580.9 (2)C16—C17—C18—O2179.39 (16)
N2—O1—C7—O6179.69 (15)C16—C17—C18—C200.3 (3)
N2—O1—C7—C80.88 (17)C19—O2—C18—C17172.59 (18)
N2—N1—C8—C7−0.05 (19)C19—O2—C18—C20−8.19 (18)
C6—N1—C8—C7176.72 (15)C18—O2—C19—O312.89 (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—C187.75 (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—C9177.31 (15)C17—C18—C20—O3179.55 (15)
N1—C8—C9—C14−177.80 (16)O2—C18—C20—O30.27 (19)
C7—C8—C9—C144.9 (3)O3—C20—C21—C15180.00 (16)
N1—C8—C9—C102.0 (3)C18—C20—C21—C15−0.3 (3)
C7—C8—C9—C10−175.23 (15)C16—C15—C21—C200.7 (2)
C14—C9—C10—C11−23.1 (2)C11—C15—C21—C20−178.98 (15)
C8—C9—C10—C11157.03 (15)C23—O5—C22—O46.4 (2)
C9—C10—C11—C15178.75 (14)C23—O5—C22—C12−171.70 (14)
C9—C10—C11—C1253.54 (18)C11—C12—C22—O434.7 (2)
C15—C11—C12—C2257.8 (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—C13178.89 (14)C13—C12—C22—O590.67 (17)
C10—C11—C12—C13−56.42 (18)C22—O5—C23—C2480.80 (19)
C22—C12—C13—O7−27.4 (2)
Cg1 is the centroid of the C1–C6 ring.
D—H···AD—HH···AD···AD—H···A
C4—H4A···O4i0.932.493.304 (3)146
C5—H5A···O7ii0.932.443.258 (2)146
C14—H14A···O60.932.292.998 (2)133
C10—H10A···Cg10.972.483.570 (2)133
Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1–C6 ring.

D—H⋯AD—HH⋯ADAD—H⋯A
C4—H4A⋯O4i0.932.493.304 (3)146
C5—H5A⋯O7ii0.932.443.258 (2)146
C14—H14A⋯O60.932.292.998 (2)133
C10—H10ACg10.972.483.570 (2)133

Symmetry codes: (i) ; (ii) .

  7 in total

1.  A short history of SHELX.

Authors:  George M Sheldrick
Journal:  Acta Crystallogr A       Date:  2007-12-21       Impact factor: 2.290

2.  Synthesis and antimicrobial activities of a new series of 4-S-[4(1)-amino-5(1)-oxo-6(1)-substituted benzyl-4(1),5(1)-dihydro-1(1),2(1),4(1)-triazin-3-yl]mercaptoacetyl-3-arylsydnones.

Authors:  Jyothi C Hegde; K S Girisha; Adithya Adhikari; Balakrishna Kalluraya
Journal:  Eur J Med Chem       Date:  2008-03-04       Impact factor: 6.514

3.  4-Formyl-3-p-tolyl-sydnone.

Authors:  Jia Hao Goh; Hoong-Kun Fun; B Kalluraya
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2010-05-08

4.  Convenient access to 1,3,4-trisubstituted pyrazoles carrying 5-nitrothiophene moiety via 1,3-dipolar cycloaddition of sydnones with acetylenic ketones and their antimicrobial evaluation.

Authors:  N Satheesha Rai; Balakrishna Kalluraya; B Lingappa; Shaliny Shenoy; Vedavati G Puranic
Journal:  Eur J Med Chem       Date:  2007-08-30       Impact factor: 6.514

5.  4-[3-(1-Naphthyl-oxymeth-yl)-7H-1,2,4-triazolo[3,4-b][1,3,4]thia-diazin-6-yl]-3-p-tolyl-sydnone.

Authors:  Jia Hao Goh; Hoong-Kun Fun; B Kalluraya
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2010-05-22

6.  4-{3-[(2-Isopropyl-5-methyl-phen-oxy)meth-yl]-7H-1,2,4-triazolo[3,4-b][1,3,4]thia-diazin-6-yl}-3-(p-tol-yl)sydnone.

Authors:  Jia Hao Goh; Hoong-Kun Fun; B Kalluraya
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2010-08-04

7.  Structure validation in chemical crystallography.

Authors:  Anthony L Spek
Journal:  Acta Crystallogr D Biol Crystallogr       Date:  2009-01-20
  7 in total
  2 in total

1.  4-{2-[2-(4-Chloro-benzyl-idene)hydrazinyl-idene]-3,6-dihydro-2H-1,3,4-thia-diazin-5-yl}-3-(4-meth-oxy-phen-yl)sydnone.

Authors:  Hoong-Kun Fun; Wan-Sin Loh; Balakrishna Kalluraya
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2011-04-22

2.  4-{2-[2-(4-Chloro-benzyl-idene)hydrazinyl-idene]-3,6-dihydro-2H-1,3,4-thia-diazin-5-yl}-3-phenyl-sydnone.

Authors:  Hoong-Kun Fun; Wan-Sin Loh; Balakrishna Kalluraya
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2011-04-22
  2 in total

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