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The title compound, C12H11N3O2S, was synthesized by a condensation reaction of 2-acetyl­indan-1,3-dione and thio­semicarbazide in ethanol in the presence of glacial acetic acid. The mol­ecule adopts a thio­ketone form. The dihedral angle between the mean planes of 1H-inden-1,3(2H)-dione and hydrazinecarbo­thio­amide units is 86.32 (7)°. Weak intra­molecular N—H...O and C—H...O hydrogen bonds are observed. In the crystal, mol­ecules are linked via pairs of weak inter­molecular N—H...O hydrogen bonds, forming inversion dimers. The dimers are further linked into a three-dimensional network through N—H...S and N—H...O hydrogen bonds, and π–π inter­actions [centroid–centroid distances = 3.5619 (10)–3.9712 (9) Å].

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2414314619015013/is5524sup1.cif
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2414314619015013/is5524Isup2.hkl
Contains datablock I

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2414314619015013/is5524Isup3.cml
Supplementary material

CCDC reference: 1857321

Key indicators

  • Single-crystal X-ray study
  • T = 99 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.063
  • wR factor = 0.173
  • Data-to-parameter ratio = 18.7

checkCIF/PLATON results

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Alert level C PLAT230_ALERT_2_C Hirshfeld Test Diff for S1 --C1 . 6.9 s.u. PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.2 Note PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ...... 3.167 Check
Alert level G PLAT063_ALERT_4_G Crystal Size Likely too Large for Beam Size .... 0.76 mm PLAT066_ALERT_1_G Predicted and Reported Tmin&Tmax Range Identical ? Check PLAT072_ALERT_2_G SHELXL First Parameter in WGHT Unusually Large 0.12 Report PLAT720_ALERT_4_G Number of Unusual/Non-Standard Labels .......... 4 Note PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min). 1 Note PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density. 5 Info
0 ALERT level A = Most likely a serious problem - resolve or explain 0 ALERT level B = A potentially serious problem, consider carefully 3 ALERT level C = Check. Ensure it is not caused by an omission or oversight 6 ALERT level G = General information/check it is not something unexpected 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 4 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: APEX2 (Bruker, 2014); cell refinement: SAINT (Bruker, 2014); data reduction: SAINT (Bruker, 2014); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015b).

2-[1-(1,3-Dioxo-1,3-dihydro-2H-inden-2-ylidene)ethyl]hydrazinecarbothioamide top
Crystal data top
C12H11N3O2SDx = 1.440 Mg m3
Mr = 261.30Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, PbcaCell parameters from 6090 reflections
a = 15.0751 (6) Åθ = 2.4–29.6°
b = 7.6891 (4) ŵ = 0.27 mm1
c = 20.7891 (9) ÅT = 99 K
V = 2409.75 (19) Å3Rod, brown
Z = 80.76 × 0.25 × 0.25 mm
F(000) = 1088
Data collection top
Bruker D8 Venture
diffractometer
2712 reflections with I > 2σ(I)
profile data from θ/2θ scansRint = 0.073
Absorption correction: multi-scan
(SADABS; Bruker, 2014)
θmax = 29.6°, θmin = 2.4°
Tmin = 0.824, Tmax = 0.937h = 2018
18247 measured reflectionsk = 810
3382 independent reflectionsl = 2828
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.063Hydrogen site location: mixed
wR(F2) = 0.173H atoms treated by a mixture of independent and constrained refinement
S = 1.07 w = 1/[σ2(Fo2) + (0.117P)2 + 0.3104P]
where P = (Fo2 + 2Fc2)/3
3382 reflections(Δ/σ)max = 0.001
181 parametersΔρmax = 0.79 e Å3
0 restraintsΔρmin = 1.00 e Å3
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S10.43388 (3)0.69858 (6)0.75750 (2)0.01816 (17)
O10.86124 (9)0.5148 (2)0.58244 (8)0.0294 (4)
O20.58261 (8)0.40510 (17)0.48472 (6)0.0202 (3)
N10.50396 (12)0.8510 (2)0.65405 (8)0.0213 (4)
HN10.4960 (17)0.948 (4)0.6726 (15)0.043 (8)*
HN20.5428 (16)0.853 (3)0.6251 (14)0.025 (6)*
N20.52093 (10)0.5557 (2)0.66273 (7)0.0162 (3)
HN30.5202 (14)0.465 (3)0.6853 (13)0.024 (6)*
N30.57075 (10)0.5469 (2)0.60634 (7)0.0150 (3)
HN40.5434 (15)0.516 (3)0.5700 (14)0.027 (6)*
C10.49117 (11)0.7065 (2)0.68685 (8)0.0152 (4)
C20.66012 (11)0.5365 (2)0.60836 (8)0.0141 (3)
C30.70518 (11)0.4833 (2)0.55397 (8)0.0151 (3)
C40.80153 (11)0.4714 (2)0.54558 (10)0.0191 (4)
C50.81627 (12)0.3939 (2)0.48089 (10)0.0209 (4)
C60.89580 (14)0.3553 (3)0.45015 (12)0.0308 (5)
H60.9513210.3773950.4701590.037*
C70.89078 (15)0.2830 (3)0.38902 (12)0.0366 (6)
H70.9440600.2567970.3666300.044*
C80.81003 (16)0.2482 (3)0.35982 (11)0.0349 (5)
H80.8092650.1978830.3180950.042*
C90.72982 (15)0.2855 (3)0.39040 (10)0.0268 (5)
H90.6743940.2617520.3705100.032*
C100.73498 (12)0.3592 (2)0.45145 (8)0.0177 (4)
C110.66251 (11)0.4159 (2)0.49572 (8)0.0149 (3)
C120.70463 (12)0.5863 (3)0.67010 (9)0.0215 (4)
H12A0.6846280.7022080.6832400.026*
H12B0.7690690.5874500.6638750.026*
H12C0.6893230.5016750.7035660.026*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0289 (3)0.0173 (3)0.0083 (2)0.00088 (16)0.00634 (15)0.00102 (15)
O10.0189 (7)0.0388 (9)0.0304 (9)0.0005 (6)0.0073 (6)0.0053 (6)
O20.0190 (6)0.0289 (7)0.0128 (6)0.0048 (5)0.0024 (5)0.0033 (5)
N10.0347 (9)0.0172 (8)0.0120 (8)0.0020 (7)0.0095 (6)0.0015 (6)
N20.0263 (8)0.0151 (7)0.0073 (7)0.0003 (6)0.0054 (6)0.0000 (6)
N30.0190 (7)0.0219 (8)0.0042 (7)0.0015 (5)0.0020 (5)0.0013 (5)
C10.0193 (8)0.0168 (8)0.0094 (8)0.0013 (6)0.0018 (6)0.0021 (6)
C20.0188 (8)0.0141 (8)0.0095 (8)0.0012 (6)0.0021 (6)0.0032 (6)
C30.0164 (8)0.0179 (8)0.0110 (8)0.0020 (6)0.0013 (6)0.0028 (6)
C40.0167 (8)0.0207 (9)0.0200 (9)0.0026 (6)0.0004 (6)0.0086 (7)
C50.0232 (9)0.0171 (9)0.0223 (10)0.0058 (7)0.0088 (7)0.0080 (7)
C60.0256 (10)0.0230 (10)0.0436 (13)0.0052 (8)0.0169 (9)0.0101 (9)
C70.0424 (13)0.0228 (11)0.0444 (14)0.0086 (9)0.0313 (11)0.0070 (9)
C80.0565 (14)0.0243 (11)0.0239 (11)0.0098 (10)0.0237 (10)0.0024 (9)
C90.0420 (12)0.0239 (10)0.0146 (9)0.0070 (8)0.0083 (8)0.0011 (7)
C100.0240 (9)0.0173 (8)0.0118 (8)0.0053 (7)0.0066 (6)0.0043 (7)
C110.0200 (8)0.0164 (8)0.0082 (8)0.0048 (6)0.0020 (6)0.0029 (6)
C120.0263 (9)0.0268 (10)0.0113 (8)0.0015 (7)0.0062 (7)0.0009 (7)
Geometric parameters (Å, º) top
S1—C11.7050 (18)C4—C51.488 (3)
O1—C41.228 (2)C5—C61.391 (3)
O2—C111.229 (2)C5—C101.395 (3)
N1—C11.318 (2)C6—C71.389 (4)
N1—HN10.85 (3)C6—H60.9500
N1—HN20.84 (3)C7—C81.386 (4)
N2—C11.340 (2)C7—H70.9500
N2—N31.394 (2)C8—C91.396 (3)
N2—HN30.84 (2)C8—H80.9500
N3—C21.350 (2)C9—C101.392 (3)
N3—HN40.89 (3)C9—H90.9500
C2—C31.381 (2)C10—C111.493 (2)
C2—C121.498 (2)C12—H12A0.9800
C3—C111.466 (2)C12—H12B0.9800
C3—C41.466 (2)C12—H12C0.9800
C1—N1—HN1119 (2)C7—C6—C5117.3 (2)
C1—N1—HN2119.0 (17)C7—C6—H6121.3
HN1—N1—HN2114 (2)C5—C6—H6121.3
C1—N2—N3122.48 (15)C8—C7—C6121.71 (18)
C1—N2—HN3120.3 (17)C8—C7—H7119.1
N3—N2—HN3115.8 (16)C6—C7—H7119.1
C2—N3—N2120.94 (15)C7—C8—C9121.4 (2)
C2—N3—HN4118.1 (15)C7—C8—H8119.3
N2—N3—HN4118.4 (15)C9—C8—H8119.3
N1—C1—N2119.14 (16)C10—C9—C8116.8 (2)
N1—C1—S1123.34 (14)C10—C9—H9121.6
N2—C1—S1117.46 (13)C8—C9—H9121.6
N3—C2—C3118.86 (15)C9—C10—C5121.78 (17)
N3—C2—C12117.30 (15)C9—C10—C11129.77 (18)
C3—C2—C12123.84 (16)C5—C10—C11108.44 (16)
C2—C3—C11124.43 (15)O2—C11—C3127.43 (15)
C2—C3—C4127.10 (16)O2—C11—C10125.64 (16)
C11—C3—C4108.34 (15)C3—C11—C10106.93 (14)
O1—C4—C3129.43 (19)C2—C12—H12A109.5
O1—C4—C5124.29 (17)C2—C12—H12B109.5
C3—C4—C5106.28 (16)H12A—C12—H12B109.5
C6—C5—C10121.0 (2)C2—C12—H12C109.5
C6—C5—C4129.0 (2)H12A—C12—H12C109.5
C10—C5—C4109.99 (15)H12B—C12—H12C109.5
C1—N2—N3—C297.7 (2)C4—C5—C6—C7179.82 (18)
N3—N2—C1—N14.8 (3)C5—C6—C7—C80.9 (3)
N3—N2—C1—S1178.07 (12)C6—C7—C8—C90.5 (3)
N2—N3—C2—C3163.37 (16)C7—C8—C9—C100.0 (3)
N2—N3—C2—C1217.4 (2)C8—C9—C10—C50.2 (3)
N3—C2—C3—C117.9 (3)C8—C9—C10—C11179.00 (18)
C12—C2—C3—C11172.90 (16)C6—C5—C10—C90.2 (3)
N3—C2—C3—C4176.93 (16)C4—C5—C10—C9179.77 (17)
C12—C2—C3—C42.3 (3)C6—C5—C10—C11179.53 (16)
C2—C3—C4—O14.8 (3)C4—C5—C10—C110.9 (2)
C11—C3—C4—O1179.40 (19)C2—C3—C11—O24.2 (3)
C2—C3—C4—C5175.41 (17)C4—C3—C11—O2179.82 (17)
C11—C3—C4—C50.42 (19)C2—C3—C11—C10175.02 (16)
O1—C4—C5—C60.3 (3)C4—C3—C11—C100.94 (19)
C3—C4—C5—C6179.83 (19)C9—C10—C11—O20.3 (3)
O1—C4—C5—C10179.86 (18)C5—C10—C11—O2179.61 (16)
C3—C4—C5—C100.3 (2)C9—C10—C11—C3179.59 (18)
C10—C5—C6—C70.7 (3)C5—C10—C11—C31.14 (19)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C12—H12B···O10.982.263.033 (3)135
N2—HN3···S1i0.84 (2)2.47 (2)3.2796 (16)163 (2)
N1—HN1···S1ii0.85 (3)2.63 (3)3.3764 (19)147 (2)
N1—HN2···O1iii0.84 (3)2.11 (3)2.816 (2)142 (2)
N3—HN4···O20.89 (3)2.05 (3)2.7592 (19)135 (2)
N3—HN4···O2iv0.89 (3)2.30 (2)3.0107 (19)137 (2)
Symmetry codes: (i) x+1, y1/2, z+3/2; (ii) x+1, y+1/2, z+3/2; (iii) x+3/2, y+1/2, z; (iv) x+1, y+1, z+1.
 

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