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The synthesis of three new polysubstituted monoterpenic thia­zolidin-4-ones, namely (Z)-3-methyl-2-{(E)-[(1R,4R)-1,7,7-tri­methylbi­cyclo­[2.2.1]heptan-2-yl­idene]hydrazinyl­idene}thia­zolidin-4-one, C14H21N3OS (2), (2Z,5Z)-5-[(di­methyl­amino)­methyl­idene]-2-{(E)-[(1R,4R)-1,7,7-tri­methylbi­cyclo­[2.2.1]heptan-2-yl­idene]hydrazinyl­idene}thia­zolidin-4-one, C16H24N4OS (3), and (2Z,5Z)-5-[(di­methyl­amino)­methyl­idene]-3-methyl-2-{(E)-[(1R,4R)-1,7,7-tri­methylbi­cyclo­[2.2.1]heptan-2-yl­idene]hydrazinyl­idene}thia­zolidin-4-one, C17H26N4OS (4), is reported, starting from the corresponding thio­semicarbazones obtained from naturally occurring (R)-camphor. All the newly obtained thia­zolidin-4-ones have been fully characterized by HRMS and 1H and 13C (1D and 2D) NMR spectroscopy. Two of them, i.e. 2 and 3, were identified by single-crystal X-ray crystallography, confirming the synthetic pathway and the spectroscopic analyses. In 3, there are two roughly identical mol­ecules within the asymmetric unit with the same absolute configuration. These two mol­ecules are linked through N—H...O hydrogen bonds, building an R22(8) graph-set motif.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229618015802/yf3154sup1.cif
Contains datablocks 2, 3, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229618015802/yf31542sup2.hkl
Contains datablock 2

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229618015802/yf31543sup3.hkl
Contains datablock 3

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229618015802/yf31542sup4.cml
Supplementary material

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229618015802/yf31543sup5.cml
Supplementary material

CCDC references: 1877619; 1877618

Computing details top

Data collection: CrysAlis PRO (Agilent, 2014) for (2); APEX2 (Bruker, 2014) for (3). Cell refinement: CrysAlis PRO (Agilent, 2014) for (2); SAINT (Bruker, 2014) for (3). Data reduction: CrysAlis PRO (Agilent, 2014) for (2); SAINT (Bruker, 2014) for (3). Program(s) used to solve structure: SHELXT (Sheldrick, 2015a) for (2); SIR97 (Altomare et al., 1999) for (3). For both structures, program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: ORTEPIII (Burnett & Johnson, 1996), ORTEP-3 for Windows (Farrugia, 2012) and PLATON (Spek, 2009). Software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015b) for (2); SHELXL2014 (Sheldrick, 2015) for (3).

(Z)-3-Methyl-2-{(E)-[(1R,4R)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-ylidene]hydrazinylidene}thiazolidin-4-one (2) top
Crystal data top
C14H21N3OSDx = 1.266 Mg m3
Mr = 279.40Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121Cell parameters from 4325 reflections
a = 7.1606 (4) Åθ = 3.5–29.2°
b = 7.2405 (3) ŵ = 0.22 mm1
c = 28.2842 (14) ÅT = 173 K
V = 1466.43 (13) Å3Box, yellow
Z = 40.5 × 0.5 × 0.24 mm
F(000) = 600
Data collection top
Agilent Xcalibu, Eos Gemini ultra
diffractometer
2832 independent reflections
Radiation source: Enhance (Mo) X-ray Source2712 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.023
Detector resolution: 16.1978 pixels mm-1θmax = 26.4°, θmin = 3.2°
ω scansh = 88
Absorption correction: multi-scan
(CrysAlis PRO; Agilent, 2014)
k = 89
Tmin = 0.648, Tmax = 1.000l = 3335
8749 measured reflections
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.034 w = 1/[σ2(Fo2) + (0.0325P)2 + 0.3996P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.078(Δ/σ)max < 0.001
S = 1.12Δρmax = 0.20 e Å3
2832 reflectionsΔρmin = 0.26 e Å3
176 parametersAbsolute structure: Flack x determined using 979 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
0 restraintsAbsolute structure parameter: 0.03 (3)
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.

Refinement. All H atoms attached to C atoms were fixed geometrically and treated as riding with C—H = 1.0Å (methine), 0.99Å(methylene) with Uiso(H) = 1.2Ueq(C) and 0.98Å (methyl) with Uiso(H) = 1.2Ueq(C).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.1977 (3)0.5139 (3)0.33344 (7)0.0191 (5)
C20.2241 (3)0.4388 (3)0.38288 (7)0.0205 (5)
C2'0.2332 (3)0.5584 (3)0.49688 (8)0.0225 (5)
C30.2527 (4)0.2324 (3)0.37895 (7)0.0252 (5)
H3A0.1536410.1631860.3957540.030*
H3B0.3763420.1946590.3912580.030*
C4'0.2348 (4)0.6307 (3)0.57771 (8)0.0313 (6)
C40.2395 (3)0.2057 (3)0.32500 (7)0.0248 (5)
H40.2964520.0884410.3130930.030*
C50.0322 (3)0.2309 (4)0.31226 (9)0.0311 (6)
H5A0.0491600.1587090.3336770.037*
H5B0.0074140.1934820.2791840.037*
C5'0.2224 (4)0.8215 (3)0.55657 (8)0.0342 (6)
H5'10.3316750.8960220.5663810.041*
H5'20.1078430.8842160.5677750.041*
C60.0028 (3)0.4399 (4)0.31904 (9)0.0258 (5)
H6A0.0902320.4641840.3441640.031*
H6B0.0402140.4982290.2893200.031*
C6'0.2552 (4)0.3016 (3)0.55360 (8)0.0350 (6)
H6'10.2621950.2839390.5879100.052*
H6'20.3673070.2501950.5387310.052*
H6'30.1443550.2384560.5412650.052*
C70.3302 (3)0.3839 (3)0.30525 (8)0.0210 (5)
C80.2220 (4)0.7210 (3)0.32843 (8)0.0278 (5)
H8A0.1265270.7844950.3471980.042*
H8B0.2088380.7558080.2951090.042*
H8C0.3462540.7565470.3397300.042*
C90.5350 (3)0.4078 (4)0.31915 (11)0.0326 (6)
H9A0.6085260.3055150.3061510.049*
H9B0.5459510.4081630.3536900.049*
H9C0.5819500.5249670.3065280.049*
C100.3155 (4)0.4025 (3)0.25156 (8)0.0289 (6)
H10A0.3611960.5244110.2419140.043*
H10B0.1848200.3886670.2419080.043*
H10C0.3911330.3064280.2364300.043*
N3'0.2427 (3)0.4982 (3)0.54306 (6)0.0248 (4)
N110.2354 (3)0.4441 (2)0.46247 (6)0.0269 (4)
N120.2173 (3)0.5427 (2)0.41931 (6)0.0244 (4)
O7'0.2374 (4)0.5983 (3)0.61961 (6)0.0509 (6)
S1'0.21740 (9)0.79994 (8)0.49270 (2)0.02633 (16)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0198 (11)0.0190 (10)0.0185 (10)0.0012 (10)0.0010 (9)0.0004 (8)
C20.0188 (10)0.0215 (10)0.0212 (10)0.0032 (10)0.0017 (10)0.0017 (8)
C2'0.0196 (11)0.0255 (10)0.0225 (11)0.0009 (10)0.0014 (10)0.0014 (9)
C30.0293 (13)0.0203 (10)0.0260 (11)0.0005 (11)0.0010 (10)0.0034 (8)
C4'0.0332 (14)0.0374 (13)0.0234 (12)0.0033 (13)0.0020 (11)0.0056 (9)
C40.0320 (13)0.0171 (10)0.0253 (10)0.0007 (11)0.0009 (10)0.0013 (8)
C50.0330 (13)0.0335 (14)0.0269 (13)0.0134 (11)0.0020 (11)0.0001 (11)
C5'0.0408 (14)0.0318 (12)0.0301 (12)0.0032 (15)0.0019 (12)0.0073 (10)
C60.0188 (11)0.0378 (15)0.0209 (12)0.0013 (11)0.0013 (10)0.0032 (11)
C6'0.0471 (16)0.0316 (12)0.0262 (11)0.0036 (16)0.0009 (11)0.0058 (10)
C70.0210 (12)0.0201 (11)0.0220 (11)0.0000 (9)0.0009 (9)0.0002 (9)
C80.0374 (13)0.0193 (10)0.0267 (11)0.0026 (12)0.0015 (11)0.0026 (8)
C90.0214 (12)0.0346 (15)0.0419 (16)0.0020 (11)0.0012 (12)0.0022 (13)
C100.0341 (14)0.0289 (12)0.0236 (12)0.0021 (11)0.0076 (11)0.0003 (9)
N3'0.0277 (11)0.0270 (9)0.0199 (9)0.0001 (10)0.0000 (9)0.0001 (7)
N110.0361 (12)0.0263 (9)0.0183 (9)0.0012 (11)0.0007 (9)0.0012 (7)
N120.0307 (10)0.0248 (9)0.0178 (8)0.0015 (10)0.0019 (9)0.0010 (7)
O7'0.0769 (16)0.0560 (11)0.0197 (9)0.0084 (14)0.0040 (11)0.0025 (8)
S1'0.0284 (3)0.0243 (3)0.0263 (3)0.0016 (3)0.0020 (3)0.0004 (2)
Geometric parameters (Å, º) top
C1—C21.512 (3)C5'—S1'1.814 (2)
C1—C81.516 (3)C5'—H5'10.9900
C1—C61.549 (3)C5'—H5'20.9900
C1—C71.556 (3)C6—H6A0.9900
C2—N121.277 (3)C6—H6B0.9900
C2—C31.512 (3)C6'—N3'1.457 (3)
C2'—N111.278 (3)C6'—H6'10.9800
C2'—N3'1.379 (3)C6'—H6'20.9800
C2'—S1'1.756 (2)C6'—H6'30.9800
C3—C41.541 (3)C7—C101.528 (3)
C3—H3A0.9900C7—C91.529 (3)
C3—H3B0.9900C8—H8A0.9800
C4'—O7'1.208 (3)C8—H8B0.9800
C4'—N3'1.373 (3)C8—H8C0.9800
C4'—C5'1.508 (3)C9—H9A0.9800
C4—C51.538 (3)C9—H9B0.9800
C4—C71.548 (3)C9—H9C0.9800
C4—H41.0000C10—H10A0.9800
C5—C61.540 (4)C10—H10B0.9800
C5—H5A0.9900C10—H10C0.9800
C5—H5B0.9900N11—N121.420 (2)
C2—C1—C8115.33 (18)C1—C6—H6A110.9
C2—C1—C6103.37 (18)C5—C6—H6B110.9
C8—C1—C6114.9 (2)C1—C6—H6B110.9
C2—C1—C7100.37 (17)H6A—C6—H6B108.9
C8—C1—C7118.72 (19)N3'—C6'—H6'1109.5
C6—C1—C7101.82 (18)N3'—C6'—H6'2109.5
N12—C2—C3130.28 (19)H6'1—C6'—H6'2109.5
N12—C2—C1121.99 (19)N3'—C6'—H6'3109.5
C3—C2—C1107.72 (17)H6'1—C6'—H6'3109.5
N11—C2'—N3'121.08 (19)H6'2—C6'—H6'3109.5
N11—C2'—S1'126.48 (17)C10—C7—C9108.1 (2)
N3'—C2'—S1'112.43 (16)C10—C7—C4113.78 (19)
C2—C3—C4100.87 (16)C9—C7—C4113.8 (2)
C2—C3—H3A111.6C10—C7—C1114.45 (18)
C4—C3—H3A111.6C9—C7—C1112.6 (2)
C2—C3—H3B111.6C4—C7—C193.67 (17)
C4—C3—H3B111.6C1—C8—H8A109.5
H3A—C3—H3B109.4C1—C8—H8B109.5
O7'—C4'—N3'124.3 (2)H8A—C8—H8B109.5
O7'—C4'—C5'124.6 (2)C1—C8—H8C109.5
N3'—C4'—C5'111.08 (19)H8A—C8—H8C109.5
C5—C4—C3106.02 (19)H8B—C8—H8C109.5
C5—C4—C7102.76 (18)C7—C9—H9A109.5
C3—C4—C7103.12 (17)C7—C9—H9B109.5
C5—C4—H4114.5H9A—C9—H9B109.5
C3—C4—H4114.5C7—C9—H9C109.5
C7—C4—H4114.5H9A—C9—H9C109.5
C4—C5—C6102.68 (19)H9B—C9—H9C109.5
C4—C5—H5A111.2C7—C10—H10A109.5
C6—C5—H5A111.2C7—C10—H10B109.5
C4—C5—H5B111.2H10A—C10—H10B109.5
C6—C5—H5B111.2C7—C10—H10C109.5
H5A—C5—H5B109.1H10A—C10—H10C109.5
C4'—C5'—S1'108.50 (16)H10B—C10—H10C109.5
C4'—C5'—H5'1110.0C4'—N3'—C2'116.97 (19)
S1'—C5'—H5'1110.0C4'—N3'—C6'122.63 (19)
C4'—C5'—H5'2110.0C2'—N3'—C6'120.38 (18)
S1'—C5'—H5'2110.0C2'—N11—N12109.14 (17)
H5'1—C5'—H5'2108.4C2—N12—N11113.21 (17)
C5—C6—C1104.45 (19)C2'—S1'—C5'90.99 (11)
C5—C6—H6A110.9
C2'—N11—N12—C2177.9 (2)
(2Z,5Z)-5-[(Dimethylamino)methylidene]-2-{(E)-[(1R,4R)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-ylidene]hydrazinylidene}thiazolidin-4-one (3) top
Crystal data top
C16H24N4OSDx = 1.226 Mg m3
Mr = 320.45Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121Cell parameters from 9991 reflections
a = 11.4988 (8) Åθ = 2.4–28.6°
b = 13.5379 (11) ŵ = 0.19 mm1
c = 22.3107 (16) ÅT = 173 K
V = 3473.1 (4) Å3Box, colourless
Z = 80.50 × 0.20 × 0.13 mm
F(000) = 1376
Data collection top
Bruker APEXII CCD
diffractometer
9022 independent reflections
Radiation source: fine-focus sealed tube7693 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.033
φ and ω scansθmax = 28.8°, θmin = 2.0°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2015)
h = 1315
Tmin = 0.708, Tmax = 0.746k = 1818
39147 measured reflectionsl = 3030
Refinement top
Refinement on F2Hydrogen site location: mixed
Least-squares matrix: fullH atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.040 w = 1/[σ2(Fo2) + (0.0485P)2 + 0.6983P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.099(Δ/σ)max = 0.002
S = 1.03Δρmax = 0.28 e Å3
9022 reflectionsΔρmin = 0.21 e Å3
413 parametersAbsolute structure: Flack x determined using 2988 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
0 restraintsAbsolute structure parameter: 0.00 (2)
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.

Refinement. All H atoms attached to C atoms were fixed geometrically and treated as riding with C—H = 1.0Å (methine), 0.99Å(methylene), 0.95Å (aromatic) with Uiso(H) = 1.2Ueq(C) and 0.98Å (methyl) with Uiso(H) = 1.2Ueq(C). The coordinates of the H atoms attached to nitrogen were freely refined with Uiso(H) = 1.2Ueq(N)

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S1'A1.08659 (5)0.70562 (4)0.83031 (2)0.02920 (13)
O1A0.84868 (16)0.66875 (14)0.70992 (8)0.0382 (4)
N11A0.9274 (2)0.81791 (16)0.89028 (9)0.0351 (5)
N12A1.01999 (19)0.81605 (16)0.93186 (9)0.0335 (5)
N3'A0.87648 (19)0.75051 (16)0.79816 (9)0.0328 (5)
H3'A0.804 (3)0.777 (2)0.7990 (13)0.039*
N52A1.1905 (2)0.56671 (16)0.71302 (9)0.0357 (5)
C2'A0.9536 (2)0.76653 (18)0.84416 (10)0.0292 (5)
C4'A0.9131 (2)0.69016 (18)0.75243 (9)0.0301 (5)
C5'A1.0313 (2)0.65877 (18)0.76165 (10)0.0289 (5)
C51A1.0848 (2)0.60552 (17)0.71755 (10)0.0315 (5)
H51A1.0371500.5940340.6834800.038*
C53A1.2765 (2)0.5692 (2)0.76051 (12)0.0427 (6)
H53A1.3351140.6195280.7513690.064*
H53B1.3140780.5044590.7637110.064*
H53C1.2383630.5853190.7985670.064*
C54A1.2309 (3)0.5277 (2)0.65554 (12)0.0434 (7)
H54A1.1648240.5217140.6280080.065*
H54B1.2660330.4625330.6616920.065*
H54C1.2887790.5726590.6384050.065*
C1A1.0720 (2)0.84707 (18)1.03649 (10)0.0304 (5)
C2A0.9924 (2)0.85193 (17)0.98259 (10)0.0272 (5)
C3A0.8795 (2)0.8975 (2)1.00306 (10)0.0336 (6)
H3A10.8127350.8530440.9955360.040*
H3A20.8653350.9618890.9833700.040*
C4A0.9031 (2)0.90982 (19)1.07083 (10)0.0344 (5)
H4A0.8502260.9576421.0913920.041*
C5A0.9033 (3)0.8066 (2)1.09801 (11)0.0479 (7)
H5A10.8352700.7678501.0843540.057*
H5A20.9033230.8094111.1423490.057*
C6A1.0179 (3)0.7623 (2)1.07398 (11)0.0456 (7)
H6A11.0026210.7036041.0486820.055*
H6A21.0700370.7430251.1073220.055*
C7A1.0323 (2)0.93912 (18)1.07211 (10)0.0298 (5)
C8A1.1990 (3)0.8366 (3)1.02210 (14)0.0576 (9)
H8A11.2107000.7783930.9966880.086*
H8A21.2431930.8288571.0593540.086*
H8A31.2258910.8956961.0008680.086*
C9A1.0578 (3)1.0365 (2)1.04000 (13)0.0472 (7)
H9A11.0101871.0891411.0575070.071*
H9A21.0392071.0297400.9973210.071*
H9A31.1402851.0529641.0445720.071*
C10A1.0831 (3)0.9443 (2)1.13555 (11)0.0431 (6)
H10A1.1669160.9566801.1331950.065*
H10B1.0692110.8815491.1562380.065*
H10C1.0455540.9980131.1577650.065*
S1'B0.40653 (6)0.77974 (4)0.67351 (2)0.03167 (14)
O1B0.64583 (16)0.81736 (14)0.79305 (8)0.0385 (4)
N11B0.5684 (2)0.67568 (18)0.61071 (9)0.0413 (6)
N12B0.4705 (2)0.66612 (18)0.57229 (9)0.0410 (5)
N3'B0.6207 (2)0.74248 (17)0.70242 (9)0.0354 (5)
H3'B0.695 (3)0.718 (2)0.7034 (13)0.042*
N52B0.3027 (2)0.91422 (16)0.79228 (10)0.0369 (5)
C2'B0.5417 (2)0.7247 (2)0.65725 (10)0.0329 (5)
C4'B0.5823 (2)0.79727 (18)0.75012 (9)0.0305 (5)
C5'B0.4623 (2)0.82584 (18)0.74221 (10)0.0293 (5)
C51B0.4090 (2)0.87789 (17)0.78691 (10)0.0313 (5)
H51B0.4574710.8903750.8205430.038*
C53B0.2159 (2)0.9115 (2)0.74494 (11)0.0405 (6)
H53D0.2540620.9199050.7060060.061*
H53E0.1596640.9650290.7510430.061*
H53F0.1753220.8478800.7458580.061*
C54B0.2648 (3)0.9568 (2)0.84936 (12)0.0473 (7)
H54D0.3323320.9663070.8755140.071*
H54E0.2093770.9120570.8687490.071*
H54F0.2272351.0207040.8420240.071*
C1B0.4138 (2)0.60855 (18)0.47219 (10)0.0325 (5)
C2B0.4995 (2)0.63107 (18)0.52138 (10)0.0292 (5)
C3B0.6185 (2)0.6022 (2)0.49946 (10)0.0330 (6)
H3B10.6538520.5507450.5251740.040*
H3B20.6712010.6598890.4972500.040*
C4B0.5893 (2)0.5622 (2)0.43705 (11)0.0382 (6)
H4B0.6568720.5591070.4089080.046*
C5B0.5282 (2)0.4636 (2)0.44726 (15)0.0493 (7)
H5B10.5705780.4229870.4770090.059*
H5B20.5212380.4259950.4093800.059*
C6B0.4080 (2)0.49411 (19)0.47107 (14)0.0428 (6)
H6B10.3944610.4672360.5117450.051*
H6B20.3453190.4708340.4441040.051*
C7B0.4900 (2)0.6300 (2)0.41649 (10)0.0360 (6)
C8B0.2974 (3)0.6591 (3)0.47758 (15)0.0538 (8)
H8B10.2603910.6398090.5153700.081*
H8B20.2477410.6395140.4439380.081*
H8B30.3085430.7308740.4769530.081*
C9B0.5251 (3)0.7389 (3)0.41185 (16)0.0642 (10)
H9B10.5881670.7459850.3825980.096*
H9B20.5516520.7623900.4510950.096*
H9B30.4580180.7781190.3988910.096*
C10B0.4338 (3)0.5985 (3)0.35703 (12)0.0556 (8)
H10D0.3624710.6366180.3505430.083*
H10E0.4149020.5279240.3586020.083*
H10F0.4881420.6107300.3240240.083*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S1'A0.0348 (3)0.0323 (3)0.0205 (2)0.0024 (2)0.0035 (2)0.0006 (2)
O1A0.0358 (10)0.0510 (11)0.0277 (9)0.0020 (8)0.0051 (8)0.0115 (8)
N11A0.0415 (12)0.0413 (12)0.0225 (9)0.0042 (10)0.0064 (9)0.0035 (8)
N12A0.0367 (12)0.0394 (12)0.0244 (9)0.0059 (9)0.0054 (8)0.0059 (8)
N3'A0.0356 (12)0.0412 (12)0.0215 (9)0.0023 (9)0.0049 (9)0.0062 (8)
N52A0.0400 (12)0.0378 (12)0.0293 (10)0.0028 (9)0.0002 (9)0.0033 (9)
C2'A0.0364 (13)0.0301 (12)0.0211 (10)0.0019 (10)0.0018 (9)0.0011 (9)
C4'A0.0348 (12)0.0343 (12)0.0214 (10)0.0052 (11)0.0000 (10)0.0012 (8)
C5'A0.0370 (13)0.0299 (12)0.0197 (10)0.0049 (10)0.0023 (9)0.0007 (9)
C51A0.0385 (13)0.0308 (11)0.0253 (10)0.0050 (11)0.0020 (11)0.0020 (9)
C53A0.0400 (15)0.0523 (17)0.0357 (13)0.0044 (13)0.0013 (12)0.0018 (12)
C54A0.0496 (16)0.0436 (16)0.0372 (15)0.0065 (13)0.0030 (12)0.0094 (12)
C1A0.0331 (13)0.0363 (12)0.0218 (10)0.0068 (10)0.0066 (9)0.0053 (9)
C2A0.0319 (13)0.0263 (11)0.0233 (10)0.0004 (9)0.0057 (9)0.0015 (9)
C3A0.0281 (14)0.0464 (14)0.0263 (12)0.0001 (11)0.0033 (10)0.0048 (10)
C4A0.0310 (13)0.0471 (14)0.0252 (11)0.0006 (12)0.0005 (10)0.0089 (10)
C5A0.0562 (18)0.0584 (17)0.0292 (12)0.0237 (16)0.0017 (12)0.0027 (11)
C6A0.077 (2)0.0292 (14)0.0300 (13)0.0013 (13)0.0172 (14)0.0014 (10)
C7A0.0319 (12)0.0309 (12)0.0266 (11)0.0029 (10)0.0052 (9)0.0048 (9)
C8A0.0391 (17)0.091 (3)0.0424 (16)0.0225 (17)0.0087 (14)0.0122 (17)
C9A0.0584 (19)0.0387 (15)0.0444 (16)0.0126 (13)0.0112 (14)0.0006 (12)
C10A0.0528 (17)0.0446 (15)0.0320 (12)0.0036 (14)0.0131 (12)0.0097 (11)
S1'B0.0363 (3)0.0342 (3)0.0245 (3)0.0002 (3)0.0040 (3)0.0021 (2)
O1B0.0377 (10)0.0513 (11)0.0266 (8)0.0007 (8)0.0039 (8)0.0105 (8)
N11B0.0394 (13)0.0574 (14)0.0271 (10)0.0077 (11)0.0074 (10)0.0121 (10)
N12B0.0395 (12)0.0559 (15)0.0276 (10)0.0081 (11)0.0047 (9)0.0099 (10)
N3'B0.0342 (12)0.0468 (13)0.0252 (10)0.0028 (10)0.0025 (9)0.0066 (9)
N52B0.0416 (13)0.0389 (12)0.0302 (10)0.0001 (10)0.0023 (9)0.0046 (9)
C2'B0.0361 (13)0.0394 (13)0.0232 (11)0.0004 (11)0.0007 (10)0.0016 (10)
C4'B0.0366 (13)0.0325 (12)0.0224 (10)0.0056 (11)0.0004 (10)0.0006 (8)
C5'B0.0364 (13)0.0298 (12)0.0216 (10)0.0053 (10)0.0027 (10)0.0006 (9)
C51B0.0384 (13)0.0290 (11)0.0267 (11)0.0034 (11)0.0023 (11)0.0006 (9)
C53B0.0374 (14)0.0482 (16)0.0360 (14)0.0020 (12)0.0017 (11)0.0053 (12)
C54B0.0535 (18)0.0491 (17)0.0391 (15)0.0078 (15)0.0051 (13)0.0113 (13)
C1B0.0275 (12)0.0402 (13)0.0297 (11)0.0040 (11)0.0048 (10)0.0059 (10)
C2B0.0294 (13)0.0327 (12)0.0256 (11)0.0003 (10)0.0012 (10)0.0047 (9)
C3B0.0283 (14)0.0404 (14)0.0302 (12)0.0037 (10)0.0038 (10)0.0067 (10)
C4B0.0277 (12)0.0556 (16)0.0312 (12)0.0002 (12)0.0012 (11)0.0142 (11)
C5B0.0398 (15)0.0415 (16)0.0666 (19)0.0059 (13)0.0185 (14)0.0179 (14)
C6B0.0338 (14)0.0387 (14)0.0559 (17)0.0102 (12)0.0122 (13)0.0010 (12)
C7B0.0421 (14)0.0411 (14)0.0248 (11)0.0029 (11)0.0051 (10)0.0029 (10)
C8B0.0373 (17)0.071 (2)0.0535 (18)0.0205 (15)0.0095 (14)0.0135 (16)
C9B0.079 (2)0.055 (2)0.058 (2)0.0194 (18)0.0142 (18)0.0209 (16)
C10B0.058 (2)0.080 (2)0.0288 (13)0.0059 (17)0.0116 (13)0.0105 (14)
Geometric parameters (Å, º) top
S1'A—C2'A1.765 (3)S1'B—C2'B1.762 (3)
S1'A—C5'A1.776 (2)S1'B—C5'B1.775 (2)
O1A—C4'A1.238 (3)O1B—C4'B1.235 (3)
N11A—C2'A1.278 (3)N11B—C2'B1.270 (3)
N11A—N12A1.412 (3)N11B—N12B1.421 (3)
N12A—C2A1.272 (3)N12B—C2B1.275 (3)
N3'A—C4'A1.373 (3)N3'B—C4'B1.370 (3)
N3'A—C2'A1.373 (3)N3'B—C2'B1.377 (3)
N3'A—H3'A0.91 (3)N3'B—H3'B0.92 (3)
N52A—C51A1.327 (3)N52B—C51B1.323 (4)
N52A—C53A1.450 (3)N52B—C53B1.454 (3)
N52A—C54A1.463 (3)N52B—C54B1.464 (3)
C4'A—C5'A1.439 (4)C4'B—C5'B1.444 (4)
C5'A—C51A1.366 (3)C5'B—C51B1.366 (3)
C51A—H51A0.9500C51B—H51B0.9500
C53A—H53A0.9800C53B—H53D0.9800
C53A—H53B0.9800C53B—H53E0.9800
C53A—H53C0.9800C53B—H53F0.9800
C54A—H54A0.9800C54B—H54D0.9800
C54A—H54B0.9800C54B—H54E0.9800
C54A—H54C0.9800C54B—H54F0.9800
C1A—C8A1.502 (4)C1B—C2B1.506 (3)
C1A—C2A1.513 (3)C1B—C8B1.507 (4)
C1A—C7A1.547 (3)C1B—C7B1.549 (4)
C1A—C6A1.550 (4)C1B—C6B1.551 (3)
C2A—C3A1.507 (4)C2B—C3B1.504 (4)
C3A—C4A1.545 (3)C3B—C4B1.531 (3)
C3A—H3A10.9900C3B—H3B10.9900
C3A—H3A20.9900C3B—H3B20.9900
C4A—C5A1.524 (4)C4B—C5B1.525 (4)
C4A—C7A1.537 (3)C4B—C7B1.535 (4)
C4A—H4A1.0000C4B—H4B1.0000
C5A—C6A1.544 (4)C5B—C6B1.538 (4)
C5A—H5A10.9900C5B—H5B10.9900
C5A—H5A20.9900C5B—H5B20.9900
C6A—H6A10.9900C6B—H6B10.9900
C6A—H6A20.9900C6B—H6B20.9900
C7A—C9A1.528 (4)C7B—C9B1.532 (4)
C7A—C10A1.533 (3)C7B—C10B1.536 (3)
C8A—H8A10.9800C8B—H8B10.9800
C8A—H8A20.9800C8B—H8B20.9800
C8A—H8A30.9800C8B—H8B30.9800
C9A—H9A10.9800C9B—H9B10.9800
C9A—H9A20.9800C9B—H9B20.9800
C9A—H9A30.9800C9B—H9B30.9800
C10A—H10A0.9800C10B—H10D0.9800
C10A—H10B0.9800C10B—H10E0.9800
C10A—H10C0.9800C10B—H10F0.9800
C2'A—S1'A—C5'A90.44 (12)C2'B—S1'B—C5'B90.44 (12)
C2'A—N11A—N12A110.0 (2)C2'B—N11B—N12B110.5 (2)
C2A—N12A—N11A112.9 (2)C2B—N12B—N11B111.3 (2)
C4'A—N3'A—C2'A116.8 (2)C4'B—N3'B—C2'B116.8 (2)
C4'A—N3'A—H3'A122.3 (18)C4'B—N3'B—H3'B118.3 (19)
C2'A—N3'A—H3'A120.9 (18)C2'B—N3'B—H3'B124.9 (19)
C51A—N52A—C53A124.0 (2)C51B—N52B—C53B124.0 (2)
C51A—N52A—C54A120.0 (2)C51B—N52B—C54B120.0 (2)
C53A—N52A—C54A115.6 (2)C53B—N52B—C54B115.9 (2)
N11A—C2'A—N3'A122.4 (2)N11B—C2'B—N3'B122.0 (2)
N11A—C2'A—S1'A126.82 (19)N11B—C2'B—S1'B127.0 (2)
N3'A—C2'A—S1'A110.78 (17)N3'B—C2'B—S1'B110.91 (17)
O1A—C4'A—N3'A121.7 (2)O1B—C4'B—N3'B122.1 (2)
O1A—C4'A—C5'A127.3 (2)O1B—C4'B—C5'B127.0 (2)
N3'A—C4'A—C5'A111.1 (2)N3'B—C4'B—C5'B111.0 (2)
C51A—C5'A—C4'A118.6 (2)C51B—C5'B—C4'B118.5 (2)
C51A—C5'A—S1'A130.4 (2)C51B—C5'B—S1'B130.5 (2)
C4'A—C5'A—S1'A110.85 (17)C4'B—C5'B—S1'B110.89 (17)
N52A—C51A—C5'A132.5 (2)N52B—C51B—C5'B132.3 (2)
N52A—C51A—H51A113.7N52B—C51B—H51B113.9
C5'A—C51A—H51A113.7C5'B—C51B—H51B113.9
N52A—C53A—H53A109.5N52B—C53B—H53D109.5
N52A—C53A—H53B109.5N52B—C53B—H53E109.5
H53A—C53A—H53B109.5H53D—C53B—H53E109.5
N52A—C53A—H53C109.5N52B—C53B—H53F109.5
H53A—C53A—H53C109.5H53D—C53B—H53F109.5
H53B—C53A—H53C109.5H53E—C53B—H53F109.5
N52A—C54A—H54A109.5N52B—C54B—H54D109.5
N52A—C54A—H54B109.5N52B—C54B—H54E109.5
H54A—C54A—H54B109.5H54D—C54B—H54E109.5
N52A—C54A—H54C109.5N52B—C54B—H54F109.5
H54A—C54A—H54C109.5H54D—C54B—H54F109.5
H54B—C54A—H54C109.5H54E—C54B—H54F109.5
C8A—C1A—C2A115.0 (2)C2B—C1B—C8B115.5 (2)
C8A—C1A—C7A118.2 (2)C2B—C1B—C7B100.14 (19)
C2A—C1A—C7A101.23 (19)C8B—C1B—C7B118.8 (2)
C8A—C1A—C6A115.8 (2)C2B—C1B—C6B104.0 (2)
C2A—C1A—C6A102.6 (2)C8B—C1B—C6B114.6 (3)
C7A—C1A—C6A101.60 (19)C7B—C1B—C6B101.5 (2)
N12A—C2A—C3A129.9 (2)N12B—C2B—C3B128.6 (2)
N12A—C2A—C1A122.7 (2)N12B—C2B—C1B123.6 (2)
C3A—C2A—C1A107.32 (19)C3B—C2B—C1B107.80 (19)
C2A—C3A—C4A100.93 (19)C2B—C3B—C4B100.9 (2)
C2A—C3A—H3A1111.6C2B—C3B—H3B1111.6
C4A—C3A—H3A1111.6C4B—C3B—H3B1111.6
C2A—C3A—H3A2111.6C2B—C3B—H3B2111.6
C4A—C3A—H3A2111.6C4B—C3B—H3B2111.6
H3A1—C3A—H3A2109.4H3B1—C3B—H3B2109.4
C5A—C4A—C7A103.2 (2)C5B—C4B—C3B105.9 (2)
C5A—C4A—C3A106.9 (2)C5B—C4B—C7B103.1 (2)
C7A—C4A—C3A102.46 (19)C3B—C4B—C7B102.9 (2)
C5A—C4A—H4A114.3C5B—C4B—H4B114.5
C7A—C4A—H4A114.3C3B—C4B—H4B114.5
C3A—C4A—H4A114.3C7B—C4B—H4B114.5
C4A—C5A—C6A102.7 (2)C4B—C5B—C6B103.3 (2)
C4A—C5A—H5A1111.2C4B—C5B—H5B1111.1
C6A—C5A—H5A1111.2C6B—C5B—H5B1111.1
C4A—C5A—H5A2111.2C4B—C5B—H5B2111.1
C6A—C5A—H5A2111.2C6B—C5B—H5B2111.1
H5A1—C5A—H5A2109.1H5B1—C5B—H5B2109.1
C5A—C6A—C1A104.0 (2)C5B—C6B—C1B103.6 (2)
C5A—C6A—H6A1111.0C5B—C6B—H6B1111.0
C1A—C6A—H6A1111.0C1B—C6B—H6B1111.0
C5A—C6A—H6A2111.0C5B—C6B—H6B2111.0
C1A—C6A—H6A2111.0C1B—C6B—H6B2111.0
H6A1—C6A—H6A2109.0H6B1—C6B—H6B2109.0
C9A—C7A—C10A108.7 (2)C9B—C7B—C4B113.6 (2)
C9A—C7A—C4A113.5 (2)C9B—C7B—C10B108.7 (2)
C10A—C7A—C4A113.4 (2)C4B—C7B—C10B113.9 (2)
C9A—C7A—C1A113.4 (2)C9B—C7B—C1B112.6 (2)
C10A—C7A—C1A113.5 (2)C4B—C7B—C1B93.96 (19)
C4A—C7A—C1A93.87 (18)C10B—C7B—C1B113.7 (2)
C1A—C8A—H8A1109.5C1B—C8B—H8B1109.5
C1A—C8A—H8A2109.5C1B—C8B—H8B2109.5
H8A1—C8A—H8A2109.5H8B1—C8B—H8B2109.5
C1A—C8A—H8A3109.5C1B—C8B—H8B3109.5
H8A1—C8A—H8A3109.5H8B1—C8B—H8B3109.5
H8A2—C8A—H8A3109.5H8B2—C8B—H8B3109.5
C7A—C9A—H9A1109.5C7B—C9B—H9B1109.5
C7A—C9A—H9A2109.5C7B—C9B—H9B2109.5
H9A1—C9A—H9A2109.5H9B1—C9B—H9B2109.5
C7A—C9A—H9A3109.5C7B—C9B—H9B3109.5
H9A1—C9A—H9A3109.5H9B1—C9B—H9B3109.5
H9A2—C9A—H9A3109.5H9B2—C9B—H9B3109.5
C7A—C10A—H10A109.5C7B—C10B—H10D109.5
C7A—C10A—H10B109.5C7B—C10B—H10E109.5
H10A—C10A—H10B109.5H10D—C10B—H10E109.5
C7A—C10A—H10C109.5C7B—C10B—H10F109.5
H10A—C10A—H10C109.5H10D—C10B—H10F109.5
H10B—C10A—H10C109.5H10E—C10B—H10F109.5
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3A—H3A···O1B0.91 (3)1.90 (3)2.805 (3)171 (3)
C53A—H53A···S1Bi0.982.903.759 (3)147
C53A—H53C···S1A0.982.493.256 (3)135
C54A—H54B···O1Bii0.982.433.381 (3)163
N3B—H3B···O1A0.92 (3)1.89 (3)2.810 (3)177 (3)
C53B—H53D···S1B0.982.683.245 (3)117
C53B—H53F···S1Aiii0.982.883.689 (3)140
C54B—H54F···O1Aiv0.982.473.418 (4)162
Symmetry codes: (i) x+1, y, z; (ii) x+2, y1/2, z+3/2; (iii) x1, y, z; (iv) x+1, y+1/2, z+3/2.
Comparison of selected geometry (Å) within the hydrazono fragment between the title compounds and some related molecules top
Ref.C2—N12N12—N11N11—C2'C2'—N3'C2'—S1'C2—N12—N11N12—N11—C2'
21.277 (3)1.420 (2)1.278 (3)1.379 (3)1.756 (2)113.21 (17)109.13 (17)
31.273 (3)1.414 (3)1.278 (3)1.372 (3)1.766 (3)112.9 (2)110.1 (2)
1.276 (3)1.421 (3)1.270 (3)1.369 (3)1.764 (3)111.1 (2)110.4 (2)
NEPPEU1.2681.3961.257114.71113.67
YIRJOY1.2751.4171.259111.82112.87
YIRJOY1.2751.4081.255113.69113.96
SOHHON1.2961.4101.2771.3911.736111.30110.04
WOGHAD1.3101.4111.2841.3831.760111.70109.65
ZEWCAH1.2721.4161.2731.3811.734113.99109.89
References: CSD refcode NEFPEU (Feddouli et al., 2006); YIRJOY (Shaw et al., 1994); SOHHON (Castiñeiras et al., 2008); WOGHAD (Castiñeiras et al., 2014); ZEWCAH (Moreira et al., 2012).
 

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