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X-ray diffraction analyses of 2-substituted cyclohexanone oximes C5H9(X)C=NOH [X = SMe (1), NMe2 (2)] and of the parent compound [X = H (3)] showed that their cyclohexyl rings are in a slightly distorted chair conformation. These compounds assume in the solid state the (E) configuration bearing the 2-substituents in the axial conformation. Compounds (1) and (2) exist as dimeric and polymeric hydrogen-bond associates, respectively. Low-temperature X-ray analysis of the cyclohexanone oxime (3) showed that the molecules are associated forming two independent trimers. The dimer in (1) and the trimer in (3) are built up via [O—H...N=C] hydrogen bonds, while the polymer of (2) is via the [OH...NMe2] hydrogen bond. The comparative IR νOH and νC=N analysis of the title compounds, in the solid state and in CCl4 solution, fully supports the nature of the associates for (1)–(3) obtained by X-ray diffraction. The IR azomethyne frequency shift analysis (ΔνC=N) also suggests the occurrence of the πC=N/σ*C—X orbital interaction which stabilizes the axial conformations of (1) and (2).

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108768101009624/na0119sup1.cif
Contains datablocks global, 3, jzs52, jzs51

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768101009624/na0119jzs52sup2.hkl
Contains datablock jzs52

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768101009624/na0119olivap3sup3.hkl
Contains datablock olivap3

CCDC references: 174979; 174980; 174981

Computing details top

Data collection: CAD-4 Software (Enraf-Nonius,1989) for jzs52, jzs51. Cell refinement: CAD-4 Software (Enraf-Nonius,1989) for jzs52, jzs51. Data reduction: CAD-4 Software (Enraf-Nonius, 1989) for jzs52, jzs51. Program(s) used to solve structure: SHELXS86 (Sheldrick, 1985) for jzs52, jzs51; SHELXS97 (Sheldrick, 1990) for (3). For all compounds, program(s) used to refine structure: SHELXL97 (Sheldrick, 1997). Molecular graphics: ZORTEP (Zsolnai, 1995) for jzs52, jzs51. Software used to prepare material for publication: SHELXL97 (Sheldrick, 1997) for jzs52, jzs51.

Figures top
[Figure 1]
[Figure 2]
[Figure 3]
[Figure 4]
[Figure 5]
[Figure 6]
[Figure 7]
[Figure 8]
[Figure 9]
(jzs52) 2-methylthio-cyclohexanone oxime top
Crystal data top
C7H13NOSF(000) = 344
Mr = 159.24Dx = 1.228 Mg m3
Monoclinic, P121/c1Mo Kα radiation, λ = 0.71073 Å
a = 5.2634 (9) ÅCell parameters from 25 reflections
b = 23.222 (3) Åθ = 9.1–18.0°
c = 7.3962 (8) ŵ = 0.31 mm1
β = 107.66 (1)°T = 293 K
V = 861.4 (2) Å3Irregular, colourless
Z = 40.30 × 0.20 × 0.20 mm
Data collection top
Enraf-Nonius CAD4
diffractometer
Rint = 0.024
Radiation source: fine-focus sealed tubeθmax = 25.5°, θmin = 3.0°
Graphite monochromatorh = 66
ω/–2θ scansk = 028
1725 measured reflectionsl = 80
1602 independent reflections3 standard reflections every 60 min
979 reflections with F2 > 2σF2 intensity decay: 1.3%
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)] = 0.036Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.102H atoms treated by a mixture of independent and constrained refinement
S = 1.00 w = 1/[σ2(Fo2) + (0.0379P)2 + 0.2459P]
where P = (Fo2 + 2Fc2)/3
1602 reflections(Δ/σ)max < 0.001
92 parametersΔρmax = 0.13 e Å3
0 restraintsΔρmin = 0.20 e Å3
Crystal data top
C7H13NOSV = 861.4 (2) Å3
Mr = 159.24Z = 4
Monoclinic, P121/c1Mo Kα radiation
a = 5.2634 (9) ŵ = 0.31 mm1
b = 23.222 (3) ÅT = 293 K
c = 7.3962 (8) Å0.30 × 0.20 × 0.20 mm
β = 107.66 (1)°
Data collection top
Enraf-Nonius CAD4
diffractometer
Rint = 0.024
1725 measured reflections3 standard reflections every 60 min
1602 independent reflections intensity decay: 1.3%
979 reflections with F2 > 2σF2
Refinement top
R[F2 > 2σ(F2)] = 0.0360 restraints
wR(F2) = 0.102H atoms treated by a mixture of independent and constrained refinement
S = 1.00Δρmax = 0.13 e Å3
1602 reflectionsΔρmin = 0.20 e Å3
92 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.

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
xyzUiso*/Ueq
S0.35292 (15)0.13345 (3)0.17276 (9)0.0699 (3)
O0.2915 (3)0.01114 (6)0.6521 (2)0.0586 (5)
H1O0.15470.01660.63970.070*
N10.1725 (4)0.05282 (7)0.5137 (2)0.0457 (5)
C10.3238 (4)0.09592 (9)0.5159 (3)0.0418 (5)
C20.5990 (4)0.10451 (9)0.6479 (3)0.0537 (6)
H1C20.72770.09580.58170.064*
H2C20.62880.07800.75370.064*
C30.6428 (5)0.16599 (11)0.7232 (4)0.0641 (7)
H1C30.54030.17220.81050.077*
H2C30.82980.17130.79270.077*
C40.5611 (5)0.20973 (10)0.5652 (4)0.0607 (7)
H1C40.67180.20540.48240.073*
H2C40.58760.24830.61840.073*
C50.2711 (5)0.20169 (9)0.4518 (4)0.0610 (7)
H1C50.22410.22950.34920.073*
H2C50.16080.20920.53310.073*
C60.2120 (4)0.14133 (9)0.3691 (3)0.0503 (6)
H1C60.01830.13630.32000.060*
C70.2027 (7)0.06699 (12)0.0733 (4)0.0837 (9)
H7A0.24860.05880.04010.126*
H7B0.01250.07000.04330.126*
H7C0.26630.03650.16340.126*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S0.0896 (5)0.0683 (5)0.0535 (4)0.0158 (4)0.0243 (3)0.0024 (3)
O0.0702 (11)0.0474 (9)0.0540 (10)0.0096 (8)0.0127 (8)0.0101 (8)
N10.0499 (11)0.0404 (10)0.0480 (10)0.0012 (9)0.0168 (9)0.0034 (9)
C10.0420 (12)0.0396 (12)0.0455 (12)0.0005 (10)0.0159 (10)0.0024 (10)
C20.0483 (14)0.0458 (13)0.0608 (14)0.0043 (11)0.0074 (12)0.0004 (12)
C30.0646 (17)0.0590 (16)0.0642 (16)0.0125 (13)0.0130 (13)0.0110 (13)
C40.0628 (16)0.0418 (13)0.0784 (17)0.0090 (12)0.0227 (14)0.0093 (13)
C50.0624 (16)0.0410 (13)0.0817 (17)0.0074 (12)0.0247 (14)0.0046 (12)
C60.0410 (12)0.0469 (13)0.0604 (14)0.0013 (10)0.0115 (10)0.0061 (11)
C70.109 (3)0.0753 (19)0.0525 (15)0.0035 (18)0.0035 (16)0.0061 (14)
Geometric parameters (Å, º) top
S—C71.787 (3)C1—C61.500 (3)
S—C61.829 (2)C2—C31.524 (3)
O—N11.410 (2)C3—C41.509 (3)
N1—C11.276 (3)C4—C51.514 (3)
C1—C21.494 (3)C5—C61.523 (3)
C7—S—C6100.24 (13)C4—C3—C2111.8 (2)
C1—N1—O113.03 (18)C3—C4—C5110.4 (2)
N1—C1—C2126.2 (2)C4—C5—C6112.64 (19)
N1—C1—C6115.85 (19)C1—C6—C5111.65 (19)
C2—C1—C6117.94 (18)C1—C6—S109.87 (15)
C1—C2—C3111.90 (19)C5—C6—S109.16 (16)
O—N1—C1—C20.5 (3)C2—C1—C6—C543.3 (3)
O—N1—C1—C6178.60 (16)N1—C1—C6—S101.24 (19)
N1—C1—C2—C3136.6 (2)C2—C1—C6—S77.9 (2)
C6—C1—C2—C344.4 (3)C4—C5—C6—C148.8 (3)
C1—C2—C3—C450.6 (3)C4—C5—C6—S72.8 (2)
C2—C3—C4—C557.8 (3)C7—S—C6—C168.30 (18)
C3—C4—C5—C657.3 (3)C7—S—C6—C5168.96 (17)
N1—C1—C6—C5137.5 (2)
(jzs51) 2-dimethylaminocyclohexanone oxime top
Crystal data top
C8H16N2ODx = 1.129 Mg m3
Mr = 156.23Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, PbcaCell parameters from 23 reflections
a = 12.5662 (6) Åθ = 9.8–18.3°
b = 10.1714 (6) ŵ = 0.08 mm1
c = 14.3863 (9) ÅT = 293 K
V = 1838.8 (2) Å3Irregular, colourless
Z = 80.40 × 0.25 × 0.10 mm
F(000) = 688
Data collection top
Enraf-Nonius CAD4
diffractometer
θmax = 25.5°, θmin = 2.8°
Radiation source: fine-focus sealed tubeh = 015
Graphite monochromatork = 120
ω/–2θ scansl = 017
1711 measured reflections3 standard reflections every 60 min
1711 independent reflections intensity decay: 0.4%
1204 reflections with F2 > 2σF2
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)] = 0.039Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.115Riding
S = 1.03 w = 1/[σ2(Fo2) + (0.0581P)2 + 0.2888P]
where P = (Fo2 + 2Fc2)/3
1711 reflections(Δ/σ)max < 0.001
103 parametersΔρmax = 0.13 e Å3
0 restraintsΔρmin = 0.15 e Å3
Crystal data top
C8H16N2OV = 1838.8 (2) Å3
Mr = 156.23Z = 8
Orthorhombic, PbcaMo Kα radiation
a = 12.5662 (6) ŵ = 0.08 mm1
b = 10.1714 (6) ÅT = 293 K
c = 14.3863 (9) Å0.40 × 0.25 × 0.10 mm
Data collection top
Enraf-Nonius CAD4
diffractometer
1204 reflections with F2 > 2σF2
1711 measured reflections3 standard reflections every 60 min
1711 independent reflections intensity decay: 0.4%
Refinement top
R[F2 > 2σ(F2)] = 0.0390 restraints
wR(F2) = 0.115Riding
S = 1.03Δρmax = 0.13 e Å3
1711 reflectionsΔρmin = 0.15 e Å3
103 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.

Refinement. Refinement on F2 for ALL reflections. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating R-factor-obs 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
xyzUiso*/Ueq
O0.05575 (9)0.35642 (12)0.35904 (8)0.0596 (4)
H1O0.07650.43280.35810.072*
N10.02743 (10)0.34050 (12)0.29412 (9)0.0470 (3)
N20.11821 (10)0.12029 (12)0.14452 (8)0.0445 (3)
C10.06343 (11)0.22353 (13)0.29175 (10)0.0385 (3)
C20.02896 (12)0.10937 (14)0.35024 (10)0.0436 (4)
H1C20.02070.13950.39720.052*
H2C20.00730.04550.31150.052*
C30.12415 (13)0.04428 (17)0.39733 (12)0.0555 (5)
H1C30.10140.03700.42650.067*
H2C30.15120.10190.44560.067*
C40.21218 (13)0.01500 (16)0.32876 (13)0.0585 (5)
H1C40.27290.02130.36150.070*
H2C40.18780.04990.28420.070*
C50.24547 (13)0.13890 (18)0.27787 (13)0.0587 (5)
H1C50.27300.20190.32240.070*
H2C50.30230.11780.23470.070*
C60.15332 (11)0.20147 (14)0.22444 (10)0.0431 (4)
H1C60.17680.28710.20090.052*
C70.02834 (15)0.1829 (2)0.09780 (13)0.0679 (5)
H1C70.03080.18840.13990.102*
H2C70.04830.26970.07830.102*
H3C70.00840.13180.04450.102*
C80.20447 (16)0.1016 (2)0.07750 (14)0.0754 (6)
H1C80.23390.18550.06100.113*
H2C80.25890.04770.10470.113*
H3C80.17720.05930.02280.113*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O0.0753 (8)0.0504 (7)0.0532 (7)0.0266 (6)0.0090 (6)0.0006 (5)
N10.0536 (8)0.0408 (7)0.0468 (7)0.0094 (6)0.0016 (6)0.0012 (6)
N20.0472 (7)0.0454 (7)0.0409 (7)0.0052 (5)0.0085 (6)0.0005 (6)
C10.0390 (7)0.0349 (7)0.0416 (8)0.0017 (6)0.0066 (6)0.0018 (6)
C20.0479 (8)0.0393 (8)0.0436 (8)0.0030 (6)0.0014 (7)0.0008 (6)
C30.0713 (11)0.0473 (9)0.0478 (9)0.0135 (8)0.0104 (8)0.0019 (7)
C40.0596 (10)0.0551 (10)0.0607 (10)0.0227 (8)0.0161 (8)0.0065 (8)
C50.0379 (8)0.0641 (11)0.0741 (12)0.0044 (8)0.0036 (9)0.0104 (9)
C60.0403 (8)0.0343 (7)0.0547 (9)0.0054 (6)0.0046 (7)0.0001 (6)
C70.0754 (12)0.0818 (13)0.0465 (9)0.0037 (11)0.0053 (9)0.0018 (9)
C80.0766 (12)0.0780 (14)0.0717 (12)0.0093 (11)0.0355 (11)0.0109 (10)
Geometric parameters (Å, º) top
O—N11.4110 (16)C1—C61.505 (2)
N1—C11.2734 (18)C2—C31.526 (2)
N2—C71.460 (2)C3—C41.512 (2)
N2—C81.463 (2)C4—C51.516 (2)
N2—C61.4827 (19)C5—C61.529 (2)
C1—C21.498 (2)
C1—N1—O112.84 (13)C1—C2—C3111.05 (12)
C7—N2—C8109.04 (14)C4—C3—C2111.67 (13)
C7—N2—C6110.13 (13)C3—C4—C5110.68 (13)
C8—N2—C6111.28 (12)C4—C5—C6112.33 (13)
N1—C1—C2127.34 (14)N2—C6—C1111.02 (11)
N1—C1—C6115.04 (13)N2—C6—C5112.54 (12)
C2—C1—C6117.58 (12)C1—C6—C5107.89 (12)
O—N1—C1—C21.6 (2)C7—N2—C6—C5178.41 (13)
O—N1—C1—C6179.27 (11)C8—N2—C6—C560.55 (17)
N1—C1—C2—C3127.75 (16)N1—C1—C6—N2109.59 (14)
C6—C1—C2—C349.83 (16)C2—C1—C6—N272.54 (15)
C1—C2—C3—C449.95 (18)N1—C1—C6—C5126.65 (14)
C2—C3—C4—C555.75 (18)C2—C1—C6—C551.22 (16)
C3—C4—C5—C659.26 (18)C4—C5—C6—N268.28 (16)
C7—N2—C6—C157.36 (15)C4—C5—C6—C154.55 (17)
C8—N2—C6—C1178.40 (13)
(3) top
Crystal data top
C6H11NOF(000) = 1116
Mr = 113.16Dx = 1.164 Mg m3
Trigonal, P3Mo Kα radiation, λ = 0.71070 Å
a = 20.9830 (3) ŵ = 0.08 mm1
c = 7.6210 (1) ÅT = 293 K
V = 2905.88 (7) Å3Prismatic, colouless
Z = 18 × × mm
Data collection top
Radiation source: fine-focus sealed tubeRint = 0.031
Graphite monochromatorθmax = 27.5°, θmin = 1.9°
12992 measured reflectionsh = 027
4440 independent reflectionsk = 2623
3993 reflections with I > 2σ(I)l = 99
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.093H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.270Calculated w = 1/[σ2(Fo2) + (0.1771P)2 + 2.9548P]
where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max = 0.146
4440 reflectionsΔρmax = 0.38 e Å3
496 parametersΔρmin = 1.14 e Å3
0 restraintsAbsolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0 (10)
Crystal data top
C6H11NOZ = 18
Mr = 113.16Mo Kα radiation
Trigonal, P3µ = 0.08 mm1
a = 20.9830 (3) ÅT = 293 K
c = 7.6210 (1) Å × × mm
V = 2905.88 (7) Å3
Data collection top
12992 measured reflections3993 reflections with I > 2σ(I)
4440 independent reflectionsRint = 0.031
Refinement top
R[F2 > 2σ(F2)] = 0.093H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.270(Δ/σ)max = 0.146
S = 1.05Δρmax = 0.38 e Å3
4440 reflectionsΔρmin = 1.14 e Å3
496 parametersAbsolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
0 restraintsAbsolute structure parameter: 0 (10)
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.

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
xyzUiso*/UeqOcc. (<1)
O10.5575 (2)0.64416 (19)0.00600.0245 (7)
H10.58250.62430.02360.050*
N10.6074 (3)0.7185 (3)0.0341 (9)0.0367 (12)
C10.5783 (3)0.7596 (3)0.0214 (8)0.0270 (10)
C20.4997 (3)0.7344 (3)0.0208 (8)0.0250 (10)
H2A0.47140.68110.01410.030*
H2B0.49650.74870.14000.030*
C30.4664 (3)0.7672 (3)0.1054 (8)0.0242 (10)
H3A0.41820.75570.06310.029*
H3B0.46030.74510.22040.029*
C40.5157 (3)0.8511 (3)0.1205 (8)0.0244 (10)
H4A0.51950.87370.00710.029*
H4B0.49410.87030.20260.029*
C50.5920 (3)0.8697 (3)0.1840 (10)0.0399 (15)
H5A0.62320.92270.19210.048*
H5B0.58820.84920.30010.048*
C60.6261 (3)0.8399 (4)0.0621 (13)0.0502 (19)
H6A0.67170.84760.11320.060*
H6B0.63810.86740.04690.060*
O20.7549 (3)0.7816 (3)0.1628 (11)0.0398 (14)0.70
H20.71120.76570.14090.048*0.70
O2A0.7561 (5)0.7818 (5)0.0074 (15)0.017 (2)*0.30
N20.7771 (3)0.7286 (3)0.0986 (16)0.080 (3)
C220.9029 (4)0.8364 (4)0.1698 (13)0.0463 (19)0.80
H22A0.87980.86550.14540.056*0.80
H22B0.91670.84290.29280.056*0.80
C22A0.9047 (8)0.8322 (8)0.0130 (19)0.001 (3)*0.20
C230.9672 (3)0.8633 (4)0.0676 (17)0.069 (3)
H23A1.00410.91010.11640.083*
H23B0.95610.87280.04990.083*
C241.0008 (4)0.8129 (5)0.053 (2)0.109 (5)
H24A1.01790.80730.16760.130*
H24B1.04240.83420.02630.130*
C250.9397 (6)0.7360 (6)0.0169 (15)0.060 (3)0.80
H25A0.92640.74190.13530.072*0.80
H25B0.95950.70310.02220.072*0.80
C25A0.9353 (8)0.7300 (8)0.195 (2)0.001 (2)*0.20
C260.8752 (4)0.7036 (4)0.0895 (14)0.055 (2)
H26A0.88540.68510.19640.065*
H26B0.83630.66200.02750.065*
C210.8482 (5)0.7572 (5)0.1384 (14)0.048 (2)0.80
C21A0.8444 (9)0.7522 (9)0.025 (2)0.003 (3)*0.20
O30.6883 (2)0.5791 (2)0.1444 (7)0.0181 (8)0.80
O3A0.6924 (17)0.5836 (17)0.060 (4)0.070 (8)*0.20
H30.71490.63660.12150.060*0.80
N30.6146 (3)0.5571 (3)0.1016 (8)0.0182 (9)0.80
N3A0.616 (3)0.561 (3)0.015 (7)0.085 (12)*0.20
C310.5715 (3)0.4866 (3)0.1150 (8)0.0138 (10)0.80
C31A0.574 (3)0.493 (3)0.054 (7)0.080 (13)*0.20
C320.5942 (3)0.4319 (3)0.1650 (8)0.0137 (9)0.80
H32A0.57810.41500.28390.016*0.80
H32B0.64740.45540.16210.016*0.80
C32A0.598 (3)0.428 (3)0.090 (7)0.077 (12)*0.20
C330.5607 (3)0.3648 (3)0.0391 (8)0.0245 (10)
H33A0.57020.32710.08430.029*
H33B0.58380.37980.07530.029*
C340.4760 (5)0.3330 (5)0.0209 (14)0.0254 (19)0.80
H34A0.45550.29140.05900.030*0.80
H34B0.45250.31600.13420.030*0.80
C34A0.493 (2)0.333 (2)0.021 (6)0.021 (9)*0.20
C350.4615 (3)0.3920 (3)0.0482 (9)0.0276 (14)0.80
H35A0.48370.40740.16340.033*0.80
H35B0.40890.37170.06110.033*0.80
C35A0.457 (3)0.397 (3)0.096 (6)0.067 (10)*0.20
C360.4916 (3)0.4581 (3)0.0702 (10)0.0383 (14)
H36A0.46290.44500.17750.046*
H36B0.48680.49680.01290.046*
O40.5786 (2)0.8895 (2)0.6333 (6)0.0292 (9)
H40.62330.90900.62060.060*
N40.5558 (2)0.94022 (19)0.5930 (6)0.0140 (7)
C410.4868 (2)0.9142 (2)0.6029 (7)0.0137 (8)
C420.4317 (3)0.8377 (3)0.6543 (10)0.0321 (12)
H42A0.41510.83750.77310.039*
H42B0.45460.80730.65210.039*
C430.3643 (3)0.8046 (4)0.5274 (11)0.0399 (14)
H43A0.37940.79650.41310.048*
H43B0.32650.75740.57220.048*
C440.3332 (3)0.8552 (3)0.5083 (8)0.0328 (12)
H44A0.29220.83390.42670.039*
H44B0.31480.86050.62100.039*
C450.3903 (3)0.9291 (3)0.4435 (8)0.0285 (11)
H45A0.36890.96060.43300.034*
H45B0.40660.92410.32800.034*
C460.4579 (3)0.9657 (2)0.5708 (8)0.0195 (9)
H46A0.49631.01110.51960.023*
H46B0.44320.97750.68120.023*
O50.6443 (3)1.0874 (3)0.5006 (10)0.0193 (11)0.80
H50.61991.03670.52550.050*0.80
O5A0.6407 (16)1.0846 (16)0.555 (4)0.029 (7)*0.20
N50.7173 (2)1.1115 (2)0.5439 (7)0.0158 (7)
C510.7590 (2)1.1812 (2)0.5367 (7)0.0156 (8)
C520.7343 (3)1.2352 (3)0.4945 (9)0.0337 (12)
H52A0.68111.21070.50290.040*
H52B0.74791.25200.37450.040*
C530.7680 (4)1.3018 (3)0.6175 (10)0.0378 (14)
H53A0.75681.33860.57430.045*
H53B0.74651.28680.73350.045*
C540.8512 (3)1.3352 (3)0.6296 (8)0.0284 (11)
H54A0.87291.35320.51510.034*
H54B0.87121.37660.70990.034*
C550.8710 (3)1.2787 (3)0.6933 (9)0.0305 (11)
H55A0.84991.26090.80850.037*
H55B0.92401.30110.70250.037*
C560.8401 (3)1.2126 (3)0.5591 (9)0.0257 (10)
H56A0.86461.22970.44680.031*
H56B0.84991.17480.60220.031*
O60.7819 (3)1.0262 (3)0.5286 (12)0.0475 (17)0.80
H60.762 (3)1.049 (3)0.528 (8)0.025 (14)*
O6A0.7831 (6)1.0273 (6)0.6440 (17)0.002 (2)*0.20
N60.7299 (2)0.9523 (2)0.5757 (10)0.0320 (10)
C610.7556 (3)0.9090 (3)0.5699 (14)0.052 (2)
C620.8324 (4)0.9285 (5)0.5085 (15)0.050 (2)0.80
H62A0.83010.91580.38540.060*0.80
H62B0.86470.98130.51910.060*0.80
C62A0.8384 (9)0.9352 (9)0.651 (2)0.004 (3)*0.20
C630.8616 (5)0.8941 (5)0.599 (3)0.142 (8)
H63A0.88150.92080.70820.171*
H63B0.90270.89780.53240.171*
C640.8083 (5)0.8091 (5)0.6473 (16)0.055 (2)0.80
H64A0.80270.77910.54530.066*0.80
H64B0.83040.79500.74030.066*0.80
C64A0.8160 (8)0.8142 (9)0.517 (2)0.003 (3)*0.20
C650.7325 (5)0.7944 (4)0.7066 (13)0.0465 (19)0.80
H65A0.69900.74170.71260.056*0.80
H65B0.73630.81470.82300.056*0.80
C65A0.7387 (8)0.7964 (8)0.461 (2)0.001 (3)*0.20
C660.7033 (3)0.8280 (3)0.5829 (9)0.0286 (11)
H66A0.65580.81920.62370.034*
H66B0.69670.80560.46810.034*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0269 (17)0.0218 (16)0.0288 (17)0.0151 (14)0.0070 (14)0.0023 (13)
N10.034 (2)0.030 (2)0.048 (3)0.017 (2)0.016 (2)0.014 (2)
C10.028 (2)0.029 (3)0.023 (2)0.013 (2)0.0029 (18)0.0077 (18)
C20.026 (2)0.023 (2)0.030 (2)0.0149 (19)0.0027 (18)0.0047 (18)
C30.015 (2)0.023 (2)0.038 (3)0.0128 (18)0.0056 (18)0.0020 (19)
C40.036 (3)0.018 (2)0.028 (2)0.020 (2)0.0010 (18)0.0010 (16)
C50.045 (3)0.022 (2)0.052 (3)0.017 (2)0.021 (3)0.011 (2)
C60.026 (3)0.036 (3)0.090 (6)0.016 (3)0.002 (3)0.007 (3)
O20.030 (3)0.027 (3)0.063 (4)0.015 (2)0.001 (3)0.002 (3)
N20.031 (3)0.026 (3)0.185 (10)0.016 (2)0.011 (4)0.012 (4)
C220.034 (4)0.040 (4)0.065 (5)0.018 (3)0.002 (3)0.002 (4)
C230.020 (3)0.020 (3)0.158 (9)0.004 (2)0.009 (4)0.020 (4)
C240.020 (3)0.050 (5)0.261 (17)0.022 (3)0.005 (6)0.036 (7)
C250.055 (5)0.072 (6)0.064 (6)0.039 (5)0.006 (4)0.021 (5)
C260.036 (3)0.041 (4)0.092 (6)0.023 (3)0.014 (4)0.016 (4)
C210.041 (4)0.039 (4)0.064 (6)0.020 (4)0.004 (4)0.002 (4)
O30.0132 (18)0.0117 (17)0.0239 (19)0.0023 (14)0.0014 (14)0.0014 (14)
N30.020 (2)0.022 (2)0.015 (2)0.013 (2)0.0033 (17)0.0025 (17)
C310.018 (2)0.017 (2)0.0078 (19)0.009 (2)0.0034 (17)0.0029 (16)
C320.015 (2)0.008 (2)0.016 (2)0.0043 (18)0.0041 (17)0.0005 (17)
C330.029 (2)0.013 (2)0.032 (2)0.0110 (18)0.0015 (19)0.0010 (17)
C340.010 (4)0.017 (3)0.036 (4)0.003 (3)0.002 (3)0.001 (2)
C350.015 (3)0.027 (3)0.024 (3)0.002 (2)0.008 (2)0.010 (2)
C360.025 (3)0.034 (3)0.055 (4)0.014 (2)0.001 (2)0.009 (3)
O40.0212 (16)0.0299 (18)0.043 (2)0.0180 (15)0.0090 (14)0.0228 (16)
N40.0180 (17)0.0137 (16)0.0104 (14)0.0079 (14)0.0011 (12)0.0032 (12)
C410.0145 (18)0.0164 (19)0.0099 (16)0.0076 (16)0.0002 (13)0.0042 (13)
C420.017 (2)0.021 (2)0.057 (3)0.0082 (19)0.007 (2)0.020 (2)
C430.026 (3)0.037 (3)0.054 (3)0.013 (2)0.002 (2)0.002 (3)
C440.027 (3)0.047 (3)0.029 (2)0.022 (2)0.0085 (19)0.006 (2)
C450.029 (2)0.042 (3)0.024 (2)0.025 (2)0.0038 (18)0.0013 (19)
C460.022 (2)0.018 (2)0.024 (2)0.0137 (18)0.0031 (17)0.0046 (16)
O50.015 (2)0.014 (2)0.019 (3)0.0001 (16)0.0068 (19)0.0078 (18)
N50.0158 (17)0.0143 (17)0.0157 (16)0.0062 (14)0.0025 (13)0.0002 (13)
C510.0159 (19)0.0158 (19)0.0142 (18)0.0072 (16)0.0018 (15)0.0020 (14)
C520.027 (3)0.019 (2)0.051 (3)0.008 (2)0.011 (2)0.001 (2)
C530.037 (3)0.024 (3)0.046 (3)0.010 (2)0.015 (2)0.004 (2)
C540.027 (2)0.025 (2)0.028 (2)0.009 (2)0.0003 (19)0.0081 (19)
C550.019 (2)0.026 (2)0.038 (3)0.0051 (19)0.0085 (19)0.006 (2)
C560.014 (2)0.021 (2)0.042 (3)0.0094 (18)0.0041 (19)0.008 (2)
O60.025 (3)0.023 (2)0.091 (6)0.010 (2)0.010 (3)0.008 (3)
N60.0128 (18)0.0164 (19)0.063 (3)0.0046 (15)0.0044 (19)0.0005 (19)
C610.022 (3)0.019 (3)0.118 (7)0.012 (2)0.020 (3)0.013 (3)
C620.032 (4)0.035 (4)0.084 (6)0.018 (3)0.014 (4)0.015 (4)
C630.041 (5)0.039 (4)0.36 (3)0.026 (4)0.028 (8)0.028 (8)
C640.053 (5)0.039 (4)0.078 (7)0.026 (4)0.000 (4)0.013 (4)
C650.050 (4)0.031 (4)0.057 (5)0.019 (3)0.001 (4)0.002 (3)
C660.025 (2)0.017 (2)0.040 (3)0.008 (2)0.007 (2)0.004 (2)
Geometric parameters (Å, º) top
O1—N11.410 (6)C34—C351.511 (12)
N1—C11.287 (7)C34A—C35A1.93 (6)
C1—C21.493 (7)C35—C361.503 (9)
C1—C61.499 (8)C35A—C361.12 (5)
C2—C31.539 (6)O4—N41.403 (5)
C3—C41.537 (7)N4—C411.268 (6)
C4—C51.525 (8)C41—C421.488 (6)
C5—C61.488 (10)C41—C461.501 (6)
O2—N21.486 (9)C42—C431.561 (8)
O2A—N21.554 (12)C43—C441.507 (9)
N2—C211.336 (11)C44—C451.492 (8)
N2—C21A1.362 (17)C45—C461.567 (7)
C22—C231.407 (12)O5—N51.391 (6)
C22—C211.492 (11)O5A—N51.42 (3)
C22A—C231.291 (17)N5—C511.276 (6)
C22A—C21A1.54 (2)C51—C561.497 (6)
C23—C241.541 (10)C51—C521.498 (7)
C24—C251.570 (13)C52—C531.532 (8)
C24—C25A1.923 (19)C53—C541.524 (8)
C25—C261.425 (13)C54—C551.519 (7)
C25A—C261.359 (17)C55—C561.579 (7)
C26—C21A1.536 (17)O6—N61.425 (7)
C26—C211.538 (11)O6A—N61.496 (12)
O3—N31.413 (6)N6—C611.267 (7)
O3A—N3A1.46 (5)C61—C661.496 (7)
N3—C311.297 (8)C61—C621.524 (9)
N3A—C31A1.28 (6)C61—C62A1.658 (17)
C31—C321.495 (7)C62—C631.351 (15)
C31—C361.511 (8)C62A—C631.250 (19)
C31A—C32A1.69 (7)C63—C64A1.584 (19)
C31A—C361.77 (5)C63—C641.603 (13)
C32—C331.550 (6)C64—C651.528 (13)
C32A—C331.52 (5)C64A—C65A1.53 (2)
C33—C34A1.24 (4)C65—C661.481 (10)
C33—C341.561 (11)C65A—C661.529 (15)
C1—N1—O1112.7 (5)C33—C34A—C35A109 (3)
N1—C1—C2126.1 (5)C36—C35—C34112.5 (5)
N1—C1—C6117.5 (5)C36—C35A—C34A120 (4)
C2—C1—C6116.2 (5)C35A—C36—C3547 (2)
C1—C2—C3112.1 (4)C35A—C36—C31111 (2)
C4—C3—C2111.3 (4)C35—C36—C31111.8 (5)
C5—C4—C3109.7 (4)C35A—C36—C31A120 (3)
C6—C5—C4111.0 (5)C35—C36—C31A86.1 (18)
C5—C6—C1114.2 (5)C31—C36—C31A45.5 (18)
C21—N2—C21A37.5 (8)C41—N4—O4114.2 (3)
C21—N2—O2106.7 (7)N4—C41—C42125.7 (4)
C21A—N2—O2121.3 (8)N4—C41—C46117.7 (4)
C21—N2—O2A115.6 (7)C42—C41—C46116.4 (4)
C21A—N2—O2A99.8 (9)C41—C42—C43111.0 (5)
O2—N2—O2A45.8 (5)C44—C43—C42111.2 (5)
C23—C22—C21114.1 (7)C45—C44—C43111.1 (5)
C23—C22A—C21A122.3 (13)C44—C45—C46111.4 (4)
C22A—C23—C2262.2 (8)C41—C46—C45109.9 (4)
C22A—C23—C24108.4 (9)C51—N5—O5114.0 (4)
C22—C23—C24116.0 (8)C51—N5—O5A116.8 (12)
C23—C24—C25108.1 (6)O5—N5—O5A17.2 (10)
C23—C24—C25A102.5 (8)N5—C51—C56118.5 (4)
C25—C24—C25A54.2 (7)N5—C51—C52125.2 (4)
C26—C25—C24112.9 (9)C56—C51—C52116.1 (4)
C26—C25A—C2497.6 (10)C51—C52—C53112.5 (5)
C25A—C26—C2571.2 (8)C54—C53—C52110.9 (5)
C25A—C26—C21A122.1 (10)C55—C54—C53111.0 (5)
C25—C26—C21A96.6 (9)C54—C55—C56109.0 (4)
C25A—C26—C2199.4 (9)C51—C56—C55109.7 (4)
C25—C26—C21113.4 (7)C61—N6—O6113.7 (5)
C21A—C26—C2132.7 (7)C61—N6—O6A113.9 (6)
N2—C21—C22127.0 (8)O6—N6—O6A34.9 (5)
N2—C21—C26110.7 (7)N6—C61—C66118.6 (5)
C22—C21—C26119.5 (7)N6—C61—C62126.1 (6)
N2—C21A—C26109.4 (11)C66—C61—C62113.7 (5)
N2—C21A—C22A127.7 (13)N6—C61—C62A120.0 (8)
C26—C21A—C22A113.2 (12)C66—C61—C62A113.8 (7)
C31—N3—O3112.3 (4)C62—C61—C62A40.0 (7)
C31A—N3A—O3A111 (4)C63—C62—C61113.6 (9)
N3—C31—C32126.1 (5)C63—C62A—C61111.0 (12)
N3—C31—C36115.9 (5)C62A—C63—C6249.7 (9)
C32—C31—C36118.0 (5)C62A—C63—C64A128.1 (11)
N3A—C31A—C32A127 (5)C62—C63—C64A99.6 (12)
N3A—C31A—C36109 (4)C62A—C63—C64113.6 (13)
C32A—C31A—C36112 (3)C62—C63—C64117.4 (8)
C31—C32—C33111.5 (4)C64A—C63—C6436.6 (7)
C33—C32A—C31A111 (4)C65—C64—C63111.7 (7)
C34A—C33—C32A111 (3)C65A—C64A—C63111.9 (11)
C34A—C33—C32116 (2)C66—C65—C64110.6 (7)
C32A—C33—C3279 (2)C66—C65A—C64A114.2 (11)
C34A—C33—C346 (2)C65—C66—C61109.9 (6)
C32A—C33—C34107 (2)C65—C66—C65A76.9 (7)
C32—C33—C34110.2 (5)C61—C66—C65A102.3 (7)
C35—C34—C33109.4 (6)

Experimental details

(jzs52)(jzs51)(3)
Crystal data
Chemical formulaC7H13NOSC8H16N2OC6H11NO
Mr159.24156.23113.16
Crystal system, space groupMonoclinic, P121/c1Orthorhombic, PbcaTrigonal, P3
Temperature (K)293293293
a, b, c (Å)5.2634 (9), 23.222 (3), 7.3962 (8)12.5662 (6), 10.1714 (6), 14.3863 (9)20.9830 (3), 20.9830 (3), 7.6210 (1)
α, β, γ (°)90, 107.66 (1), 9090, 90, 9090, 90, 120
V3)861.4 (2)1838.8 (2)2905.88 (7)
Z4818
Radiation typeMo KαMo KαMo Kα
µ (mm1)0.310.080.08
Crystal size (mm)0.30 × 0.20 × 0.200.40 × 0.25 × 0.10 × ×
Data collection
DiffractometerEnraf-Nonius CAD4
diffractometer
Enraf-Nonius CAD4
diffractometer
?
Absorption correction
No. of measured, independent and
observed reflections
1725, 1602, 979 (F2 > 2σF2)1711, 1711, 1204 (F2 > 2σF2)12992, 4440, 3993 [I > 2σ(I)]
Rint0.024?0.031
(sin θ/λ)max1)0.6060.6050.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.036, 0.102, 1.00 0.039, 0.115, 1.03 0.093, 0.270, 1.05
No. of reflections160217114440
No. of parameters92103496
H-atom treatmentH atoms treated by a mixture of independent and constrained refinementRidingH atoms treated by a mixture of independent and constrained refinement
(Δ/σ)max< 0.001< 0.0010.146
Δρmax, Δρmin (e Å3)0.13, 0.200.13, 0.150.38, 1.14
Absolute structure??Flack H D (1983), Acta Cryst. A39, 876-881
Absolute structure parameter??0 (10)

Computer programs: CAD-4 Software (Enraf-Nonius,1989), CAD-4 Software (Enraf-Nonius, 1989), SHELXS86 (Sheldrick, 1985), SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), ZORTEP (Zsolnai, 1995).

 

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