X-ray diffraction analyses of 2-substituted cyclohexanone oximes C
5H
9(
X)C=NOH [
X = SMe (1), NMe
2 (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

NMe
2] hydrogen bond. The comparative IR ν
OH and ν
C=N analysis of the title compounds, in the solid state and in CCl
4 solution, fully supports the nature of the associates for (1)–(3) obtained by X-ray diffraction. The IR azomethyne frequency shift analysis (Δν
C=N) also suggests the occurrence of the π
C=N/σ*
C—X orbital interaction which stabilizes the axial conformations of (1) and (2).
Supporting information
CCDC references: 174979; 174980; 174981
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.
(jzs52) 2-methylthio-cyclohexanone oxime
top
Crystal data top
C7H13NOS | F(000) = 344 |
Mr = 159.24 | Dx = 1.228 Mg m−3 |
Monoclinic, P121/c1 | Mo Kα radiation, λ = 0.71073 Å |
a = 5.2634 (9) Å | Cell parameters from 25 reflections |
b = 23.222 (3) Å | θ = 9.1–18.0° |
c = 7.3962 (8) Å | µ = 0.31 mm−1 |
β = 107.66 (1)° | T = 293 K |
V = 861.4 (2) Å3 | Irregular, colourless |
Z = 4 | 0.30 × 0.20 × 0.20 mm |
Data collection top
Enraf-Nonius CAD4 diffractometer | Rint = 0.024 |
Radiation source: fine-focus sealed tube | θmax = 25.5°, θmin = 3.0° |
Graphite monochromator | h = −6→6 |
ω/–2θ scans | k = 0→28 |
1725 measured reflections | l = −8→0 |
1602 independent reflections | 3 standard reflections every 60 min |
979 reflections with F2 > 2σF2 | intensity decay: 1.3% |
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)] = 0.036 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.102 | H 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 parameters | Δρmax = 0.13 e Å−3 |
0 restraints | Δρmin = −0.20 e Å−3 |
Crystal data top
C7H13NOS | V = 861.4 (2) Å3 |
Mr = 159.24 | Z = 4 |
Monoclinic, P121/c1 | Mo Kα radiation |
a = 5.2634 (9) Å | µ = 0.31 mm−1 |
b = 23.222 (3) Å | T = 293 K |
c = 7.3962 (8) Å | 0.30 × 0.20 × 0.20 mm |
β = 107.66 (1)° | |
Data collection top
Enraf-Nonius CAD4 diffractometer | Rint = 0.024 |
1725 measured reflections | 3 standard reflections every 60 min |
1602 independent reflections | intensity decay: 1.3% |
979 reflections with F2 > 2σF2 | |
Refinement top
R[F2 > 2σ(F2)] = 0.036 | 0 restraints |
wR(F2) = 0.102 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.00 | Δρmax = 0.13 e Å−3 |
1602 reflections | Δρmin = −0.20 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
S | 0.35292 (15) | 0.13345 (3) | 0.17276 (9) | 0.0699 (3) | |
O | 0.2915 (3) | 0.01114 (6) | 0.6521 (2) | 0.0586 (5) | |
H1O | 0.1547 | −0.0166 | 0.6397 | 0.070* | |
N1 | 0.1725 (4) | 0.05282 (7) | 0.5137 (2) | 0.0457 (5) | |
C1 | 0.3238 (4) | 0.09592 (9) | 0.5159 (3) | 0.0418 (5) | |
C2 | 0.5990 (4) | 0.10451 (9) | 0.6479 (3) | 0.0537 (6) | |
H1C2 | 0.7277 | 0.0958 | 0.5817 | 0.064* | |
H2C2 | 0.6288 | 0.0780 | 0.7537 | 0.064* | |
C3 | 0.6428 (5) | 0.16599 (11) | 0.7232 (4) | 0.0641 (7) | |
H1C3 | 0.5403 | 0.1722 | 0.8105 | 0.077* | |
H2C3 | 0.8298 | 0.1713 | 0.7927 | 0.077* | |
C4 | 0.5611 (5) | 0.20973 (10) | 0.5652 (4) | 0.0607 (7) | |
H1C4 | 0.6718 | 0.2054 | 0.4824 | 0.073* | |
H2C4 | 0.5876 | 0.2483 | 0.6184 | 0.073* | |
C5 | 0.2711 (5) | 0.20169 (9) | 0.4518 (4) | 0.0610 (7) | |
H1C5 | 0.2241 | 0.2295 | 0.3492 | 0.073* | |
H2C5 | 0.1608 | 0.2092 | 0.5331 | 0.073* | |
C6 | 0.2120 (4) | 0.14133 (9) | 0.3691 (3) | 0.0503 (6) | |
H1C6 | 0.0183 | 0.1363 | 0.3200 | 0.060* | |
C7 | 0.2027 (7) | 0.06699 (12) | 0.0733 (4) | 0.0837 (9) | |
H7A | 0.2486 | 0.0588 | −0.0401 | 0.126* | |
H7B | 0.0125 | 0.0700 | 0.0433 | 0.126* | |
H7C | 0.2663 | 0.0365 | 0.1634 | 0.126* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
S | 0.0896 (5) | 0.0683 (5) | 0.0535 (4) | −0.0158 (4) | 0.0243 (3) | 0.0024 (3) |
O | 0.0702 (11) | 0.0474 (9) | 0.0540 (10) | −0.0096 (8) | 0.0127 (8) | 0.0101 (8) |
N1 | 0.0499 (11) | 0.0404 (10) | 0.0480 (10) | −0.0012 (9) | 0.0168 (9) | 0.0034 (9) |
C1 | 0.0420 (12) | 0.0396 (12) | 0.0455 (12) | −0.0005 (10) | 0.0159 (10) | −0.0024 (10) |
C2 | 0.0483 (14) | 0.0458 (13) | 0.0608 (14) | −0.0043 (11) | 0.0074 (12) | −0.0004 (12) |
C3 | 0.0646 (17) | 0.0590 (16) | 0.0642 (16) | −0.0125 (13) | 0.0130 (13) | −0.0110 (13) |
C4 | 0.0628 (16) | 0.0418 (13) | 0.0784 (17) | −0.0090 (12) | 0.0227 (14) | −0.0093 (13) |
C5 | 0.0624 (16) | 0.0410 (13) | 0.0817 (17) | 0.0074 (12) | 0.0247 (14) | 0.0046 (12) |
C6 | 0.0410 (12) | 0.0469 (13) | 0.0604 (14) | 0.0013 (10) | 0.0115 (10) | 0.0061 (11) |
C7 | 0.109 (3) | 0.0753 (19) | 0.0525 (15) | −0.0035 (18) | 0.0035 (16) | −0.0061 (14) |
Geometric parameters (Å, º) top
S—C7 | 1.787 (3) | C1—C6 | 1.500 (3) |
S—C6 | 1.829 (2) | C2—C3 | 1.524 (3) |
O—N1 | 1.410 (2) | C3—C4 | 1.509 (3) |
N1—C1 | 1.276 (3) | C4—C5 | 1.514 (3) |
C1—C2 | 1.494 (3) | C5—C6 | 1.523 (3) |
| | | |
C7—S—C6 | 100.24 (13) | C4—C3—C2 | 111.8 (2) |
C1—N1—O | 113.03 (18) | C3—C4—C5 | 110.4 (2) |
N1—C1—C2 | 126.2 (2) | C4—C5—C6 | 112.64 (19) |
N1—C1—C6 | 115.85 (19) | C1—C6—C5 | 111.65 (19) |
C2—C1—C6 | 117.94 (18) | C1—C6—S | 109.87 (15) |
C1—C2—C3 | 111.90 (19) | C5—C6—S | 109.16 (16) |
| | | |
O—N1—C1—C2 | −0.5 (3) | C2—C1—C6—C5 | −43.3 (3) |
O—N1—C1—C6 | 178.60 (16) | N1—C1—C6—S | −101.24 (19) |
N1—C1—C2—C3 | −136.6 (2) | C2—C1—C6—S | 77.9 (2) |
C6—C1—C2—C3 | 44.4 (3) | C4—C5—C6—C1 | 48.8 (3) |
C1—C2—C3—C4 | −50.6 (3) | C4—C5—C6—S | −72.8 (2) |
C2—C3—C4—C5 | 57.8 (3) | C7—S—C6—C1 | 68.30 (18) |
C3—C4—C5—C6 | −57.3 (3) | C7—S—C6—C5 | −168.96 (17) |
N1—C1—C6—C5 | 137.5 (2) | | |
(jzs51) 2-dimethylaminocyclohexanone oxime
top
Crystal data top
C8H16N2O | Dx = 1.129 Mg m−3 |
Mr = 156.23 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, Pbca | Cell parameters from 23 reflections |
a = 12.5662 (6) Å | θ = 9.8–18.3° |
b = 10.1714 (6) Å | µ = 0.08 mm−1 |
c = 14.3863 (9) Å | T = 293 K |
V = 1838.8 (2) Å3 | Irregular, colourless |
Z = 8 | 0.40 × 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 tube | h = 0→15 |
Graphite monochromator | k = −12→0 |
ω/–2θ scans | l = 0→17 |
1711 measured reflections | 3 standard reflections every 60 min |
1711 independent reflections | intensity decay: 0.4% |
1204 reflections with F2 > 2σF2 | |
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)] = 0.039 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.115 | Riding |
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 parameters | Δρmax = 0.13 e Å−3 |
0 restraints | Δρmin = −0.15 e Å−3 |
Crystal data top
C8H16N2O | V = 1838.8 (2) Å3 |
Mr = 156.23 | Z = 8 |
Orthorhombic, Pbca | Mo Kα radiation |
a = 12.5662 (6) Å | µ = 0.08 mm−1 |
b = 10.1714 (6) Å | T = 293 K |
c = 14.3863 (9) Å | 0.40 × 0.25 × 0.10 mm |
Data collection top
Enraf-Nonius CAD4 diffractometer | 1204 reflections with F2 > 2σF2 |
1711 measured reflections | 3 standard reflections every 60 min |
1711 independent reflections | intensity decay: 0.4% |
Refinement top
R[F2 > 2σ(F2)] = 0.039 | 0 restraints |
wR(F2) = 0.115 | Riding |
S = 1.03 | Δρmax = 0.13 e Å−3 |
1711 reflections | Δρmin = −0.15 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
O | −0.05575 (9) | 0.35642 (12) | −0.35904 (8) | 0.0596 (4) | |
H1O | −0.0765 | 0.4328 | −0.3581 | 0.072* | |
N1 | 0.02743 (10) | 0.34050 (12) | −0.29412 (9) | 0.0470 (3) | |
N2 | 0.11821 (10) | 0.12029 (12) | −0.14452 (8) | 0.0445 (3) | |
C1 | 0.06343 (11) | 0.22353 (13) | −0.29175 (10) | 0.0385 (3) | |
C2 | 0.02896 (12) | 0.10937 (14) | −0.35024 (10) | 0.0436 (4) | |
H1C2 | −0.0207 | 0.1395 | −0.3972 | 0.052* | |
H2C2 | −0.0073 | 0.0455 | −0.3115 | 0.052* | |
C3 | 0.12415 (13) | 0.04428 (17) | −0.39733 (12) | 0.0555 (5) | |
H1C3 | 0.1014 | −0.0370 | −0.4265 | 0.067* | |
H2C3 | 0.1512 | 0.1019 | −0.4456 | 0.067* | |
C4 | 0.21218 (13) | 0.01500 (16) | −0.32876 (13) | 0.0585 (5) | |
H1C4 | 0.2729 | −0.0213 | −0.3615 | 0.070* | |
H2C4 | 0.1878 | −0.0499 | −0.2842 | 0.070* | |
C5 | 0.24547 (13) | 0.13890 (18) | −0.27787 (13) | 0.0587 (5) | |
H1C5 | 0.2730 | 0.2019 | −0.3224 | 0.070* | |
H2C5 | 0.3023 | 0.1178 | −0.2347 | 0.070* | |
C6 | 0.15332 (11) | 0.20147 (14) | −0.22444 (10) | 0.0431 (4) | |
H1C6 | 0.1768 | 0.2871 | −0.2009 | 0.052* | |
C7 | 0.02834 (15) | 0.1829 (2) | −0.09780 (13) | 0.0679 (5) | |
H1C7 | −0.0308 | 0.1884 | −0.1399 | 0.102* | |
H2C7 | 0.0483 | 0.2697 | −0.0783 | 0.102* | |
H3C7 | 0.0084 | 0.1318 | −0.0445 | 0.102* | |
C8 | 0.20447 (16) | 0.1016 (2) | −0.07750 (14) | 0.0754 (6) | |
H1C8 | 0.2339 | 0.1855 | −0.0610 | 0.113* | |
H2C8 | 0.2589 | 0.0477 | −0.1047 | 0.113* | |
H3C8 | 0.1772 | 0.0593 | −0.0228 | 0.113* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O | 0.0753 (8) | 0.0504 (7) | 0.0532 (7) | 0.0266 (6) | −0.0090 (6) | 0.0006 (5) |
N1 | 0.0536 (8) | 0.0408 (7) | 0.0468 (7) | 0.0094 (6) | 0.0016 (6) | 0.0012 (6) |
N2 | 0.0472 (7) | 0.0454 (7) | 0.0409 (7) | −0.0052 (5) | −0.0085 (6) | −0.0005 (6) |
C1 | 0.0390 (7) | 0.0349 (7) | 0.0416 (8) | 0.0017 (6) | 0.0066 (6) | 0.0018 (6) |
C2 | 0.0479 (8) | 0.0393 (8) | 0.0436 (8) | 0.0030 (6) | −0.0014 (7) | −0.0008 (6) |
C3 | 0.0713 (11) | 0.0473 (9) | 0.0478 (9) | 0.0135 (8) | 0.0104 (8) | −0.0019 (7) |
C4 | 0.0596 (10) | 0.0551 (10) | 0.0607 (10) | 0.0227 (8) | 0.0161 (8) | 0.0065 (8) |
C5 | 0.0379 (8) | 0.0641 (11) | 0.0741 (12) | 0.0044 (8) | 0.0036 (9) | 0.0104 (9) |
C6 | 0.0403 (8) | 0.0343 (7) | 0.0547 (9) | −0.0054 (6) | −0.0046 (7) | 0.0001 (6) |
C7 | 0.0754 (12) | 0.0818 (13) | 0.0465 (9) | 0.0037 (11) | 0.0053 (9) | −0.0018 (9) |
C8 | 0.0766 (12) | 0.0780 (14) | 0.0717 (12) | −0.0093 (11) | −0.0355 (11) | 0.0109 (10) |
Geometric parameters (Å, º) top
O—N1 | 1.4110 (16) | C1—C6 | 1.505 (2) |
N1—C1 | 1.2734 (18) | C2—C3 | 1.526 (2) |
N2—C7 | 1.460 (2) | C3—C4 | 1.512 (2) |
N2—C8 | 1.463 (2) | C4—C5 | 1.516 (2) |
N2—C6 | 1.4827 (19) | C5—C6 | 1.529 (2) |
C1—C2 | 1.498 (2) | | |
| | | |
C1—N1—O | 112.84 (13) | C1—C2—C3 | 111.05 (12) |
C7—N2—C8 | 109.04 (14) | C4—C3—C2 | 111.67 (13) |
C7—N2—C6 | 110.13 (13) | C3—C4—C5 | 110.68 (13) |
C8—N2—C6 | 111.28 (12) | C4—C5—C6 | 112.33 (13) |
N1—C1—C2 | 127.34 (14) | N2—C6—C1 | 111.02 (11) |
N1—C1—C6 | 115.04 (13) | N2—C6—C5 | 112.54 (12) |
C2—C1—C6 | 117.58 (12) | C1—C6—C5 | 107.89 (12) |
| | | |
O—N1—C1—C2 | 1.6 (2) | C7—N2—C6—C5 | −178.41 (13) |
O—N1—C1—C6 | 179.27 (11) | C8—N2—C6—C5 | 60.55 (17) |
N1—C1—C2—C3 | 127.75 (16) | N1—C1—C6—N2 | 109.59 (14) |
C6—C1—C2—C3 | −49.83 (16) | C2—C1—C6—N2 | −72.54 (15) |
C1—C2—C3—C4 | 49.95 (18) | N1—C1—C6—C5 | −126.65 (14) |
C2—C3—C4—C5 | −55.75 (18) | C2—C1—C6—C5 | 51.22 (16) |
C3—C4—C5—C6 | 59.26 (18) | C4—C5—C6—N2 | 68.28 (16) |
C7—N2—C6—C1 | −57.36 (15) | C4—C5—C6—C1 | −54.55 (17) |
C8—N2—C6—C1 | −178.40 (13) | | |
Crystal data top
C6H11NO | F(000) = 1116 |
Mr = 113.16 | Dx = 1.164 Mg m−3 |
Trigonal, P3 | Mo Kα radiation, λ = 0.71070 Å |
a = 20.9830 (3) Å | µ = 0.08 mm−1 |
c = 7.6210 (1) Å | T = 293 K |
V = 2905.88 (7) Å3 | Prismatic, colouless |
Z = 18 | × × mm |
Data collection top
Radiation source: fine-focus sealed tube | Rint = 0.031 |
Graphite monochromator | θmax = 27.5°, θmin = 1.9° |
12992 measured reflections | h = 0→27 |
4440 independent reflections | k = −26→23 |
3993 reflections with I > 2σ(I) | l = −9→9 |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.093 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.270 | Calculated w = 1/[σ2(Fo2) + (0.1771P)2 + 2.9548P] where P = (Fo2 + 2Fc2)/3 |
S = 1.05 | (Δ/σ)max = 0.146 |
4440 reflections | Δρmax = 0.38 e Å−3 |
496 parameters | Δρmin = −1.14 e Å−3 |
0 restraints | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0 (10) |
Crystal data top
C6H11NO | Z = 18 |
Mr = 113.16 | Mo Kα radiation |
Trigonal, P3 | µ = 0.08 mm−1 |
a = 20.9830 (3) Å | T = 293 K |
c = 7.6210 (1) Å | × × mm |
V = 2905.88 (7) Å3 | |
Data collection top
12992 measured reflections | 3993 reflections with I > 2σ(I) |
4440 independent reflections | Rint = 0.031 |
Refinement top
R[F2 > 2σ(F2)] = 0.093 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.270 | (Δ/σ)max = 0.146 |
S = 1.05 | Δρmax = 0.38 e Å−3 |
4440 reflections | Δρmin = −1.14 e Å−3 |
496 parameters | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
0 restraints | Absolute 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 | x | y | z | Uiso*/Ueq | Occ. (<1) |
O1 | 0.5575 (2) | 0.64416 (19) | −0.0060 | 0.0245 (7) | |
H1 | 0.5825 | 0.6243 | 0.0236 | 0.050* | |
N1 | 0.6074 (3) | 0.7185 (3) | 0.0341 (9) | 0.0367 (12) | |
C1 | 0.5783 (3) | 0.7596 (3) | 0.0214 (8) | 0.0270 (10) | |
C2 | 0.4997 (3) | 0.7344 (3) | −0.0208 (8) | 0.0250 (10) | |
H2A | 0.4714 | 0.6811 | −0.0141 | 0.030* | |
H2B | 0.4965 | 0.7487 | −0.1400 | 0.030* | |
C3 | 0.4664 (3) | 0.7672 (3) | 0.1054 (8) | 0.0242 (10) | |
H3A | 0.4182 | 0.7557 | 0.0631 | 0.029* | |
H3B | 0.4603 | 0.7451 | 0.2204 | 0.029* | |
C4 | 0.5157 (3) | 0.8511 (3) | 0.1205 (8) | 0.0244 (10) | |
H4A | 0.5195 | 0.8737 | 0.0071 | 0.029* | |
H4B | 0.4941 | 0.8703 | 0.2026 | 0.029* | |
C5 | 0.5920 (3) | 0.8697 (3) | 0.1840 (10) | 0.0399 (15) | |
H5A | 0.6232 | 0.9227 | 0.1921 | 0.048* | |
H5B | 0.5882 | 0.8492 | 0.3001 | 0.048* | |
C6 | 0.6261 (3) | 0.8399 (4) | 0.0621 (13) | 0.0502 (19) | |
H6A | 0.6717 | 0.8476 | 0.1132 | 0.060* | |
H6B | 0.6381 | 0.8674 | −0.0469 | 0.060* | |
O2 | 0.7549 (3) | 0.7816 (3) | 0.1628 (11) | 0.0398 (14) | 0.70 |
H2 | 0.7112 | 0.7657 | 0.1409 | 0.048* | 0.70 |
O2A | 0.7561 (5) | 0.7818 (5) | 0.0074 (15) | 0.017 (2)* | 0.30 |
N2 | 0.7771 (3) | 0.7286 (3) | 0.0986 (16) | 0.080 (3) | |
C22 | 0.9029 (4) | 0.8364 (4) | 0.1698 (13) | 0.0463 (19) | 0.80 |
H22A | 0.8798 | 0.8655 | 0.1454 | 0.056* | 0.80 |
H22B | 0.9167 | 0.8429 | 0.2928 | 0.056* | 0.80 |
C22A | 0.9047 (8) | 0.8322 (8) | −0.0130 (19) | 0.001 (3)* | 0.20 |
C23 | 0.9672 (3) | 0.8633 (4) | 0.0676 (17) | 0.069 (3) | |
H23A | 1.0041 | 0.9101 | 0.1164 | 0.083* | |
H23B | 0.9561 | 0.8728 | −0.0499 | 0.083* | |
C24 | 1.0008 (4) | 0.8129 (5) | 0.053 (2) | 0.109 (5) | |
H24A | 1.0179 | 0.8073 | 0.1676 | 0.130* | |
H24B | 1.0424 | 0.8342 | −0.0263 | 0.130* | |
C25 | 0.9397 (6) | 0.7360 (6) | −0.0169 (15) | 0.060 (3) | 0.80 |
H25A | 0.9264 | 0.7419 | −0.1353 | 0.072* | 0.80 |
H25B | 0.9595 | 0.7031 | −0.0222 | 0.072* | 0.80 |
C25A | 0.9353 (8) | 0.7300 (8) | 0.195 (2) | 0.001 (2)* | 0.20 |
C26 | 0.8752 (4) | 0.7036 (4) | 0.0895 (14) | 0.055 (2) | |
H26A | 0.8854 | 0.6851 | 0.1964 | 0.065* | |
H26B | 0.8363 | 0.6620 | 0.0275 | 0.065* | |
C21 | 0.8482 (5) | 0.7572 (5) | 0.1384 (14) | 0.048 (2) | 0.80 |
C21A | 0.8444 (9) | 0.7522 (9) | 0.025 (2) | 0.003 (3)* | 0.20 |
O3 | 0.6883 (2) | 0.5791 (2) | 0.1444 (7) | 0.0181 (8) | 0.80 |
O3A | 0.6924 (17) | 0.5836 (17) | −0.060 (4) | 0.070 (8)* | 0.20 |
H3 | 0.7149 | 0.6366 | 0.1215 | 0.060* | 0.80 |
N3 | 0.6146 (3) | 0.5571 (3) | 0.1016 (8) | 0.0182 (9) | 0.80 |
N3A | 0.616 (3) | 0.561 (3) | −0.015 (7) | 0.085 (12)* | 0.20 |
C31 | 0.5715 (3) | 0.4866 (3) | 0.1150 (8) | 0.0138 (10) | 0.80 |
C31A | 0.574 (3) | 0.493 (3) | −0.054 (7) | 0.080 (13)* | 0.20 |
C32 | 0.5942 (3) | 0.4319 (3) | 0.1650 (8) | 0.0137 (9) | 0.80 |
H32A | 0.5781 | 0.4150 | 0.2839 | 0.016* | 0.80 |
H32B | 0.6474 | 0.4554 | 0.1621 | 0.016* | 0.80 |
C32A | 0.598 (3) | 0.428 (3) | −0.090 (7) | 0.077 (12)* | 0.20 |
C33 | 0.5607 (3) | 0.3648 (3) | 0.0391 (8) | 0.0245 (10) | |
H33A | 0.5702 | 0.3271 | 0.0843 | 0.029* | |
H33B | 0.5838 | 0.3798 | −0.0753 | 0.029* | |
C34 | 0.4760 (5) | 0.3330 (5) | 0.0209 (14) | 0.0254 (19) | 0.80 |
H34A | 0.4555 | 0.2914 | −0.0590 | 0.030* | 0.80 |
H34B | 0.4525 | 0.3160 | 0.1342 | 0.030* | 0.80 |
C34A | 0.493 (2) | 0.333 (2) | 0.021 (6) | 0.021 (9)* | 0.20 |
C35 | 0.4615 (3) | 0.3920 (3) | −0.0482 (9) | 0.0276 (14) | 0.80 |
H35A | 0.4837 | 0.4074 | −0.1634 | 0.033* | 0.80 |
H35B | 0.4089 | 0.3717 | −0.0611 | 0.033* | 0.80 |
C35A | 0.457 (3) | 0.397 (3) | 0.096 (6) | 0.067 (10)* | 0.20 |
C36 | 0.4916 (3) | 0.4581 (3) | 0.0702 (10) | 0.0383 (14) | |
H36A | 0.4629 | 0.4450 | 0.1775 | 0.046* | |
H36B | 0.4868 | 0.4968 | 0.0129 | 0.046* | |
O4 | 0.5786 (2) | 0.8895 (2) | 0.6333 (6) | 0.0292 (9) | |
H4 | 0.6233 | 0.9090 | 0.6206 | 0.060* | |
N4 | 0.5558 (2) | 0.94022 (19) | 0.5930 (6) | 0.0140 (7) | |
C41 | 0.4868 (2) | 0.9142 (2) | 0.6029 (7) | 0.0137 (8) | |
C42 | 0.4317 (3) | 0.8377 (3) | 0.6543 (10) | 0.0321 (12) | |
H42A | 0.4151 | 0.8375 | 0.7731 | 0.039* | |
H42B | 0.4546 | 0.8073 | 0.6521 | 0.039* | |
C43 | 0.3643 (3) | 0.8046 (4) | 0.5274 (11) | 0.0399 (14) | |
H43A | 0.3794 | 0.7965 | 0.4131 | 0.048* | |
H43B | 0.3265 | 0.7574 | 0.5722 | 0.048* | |
C44 | 0.3332 (3) | 0.8552 (3) | 0.5083 (8) | 0.0328 (12) | |
H44A | 0.2922 | 0.8339 | 0.4267 | 0.039* | |
H44B | 0.3148 | 0.8605 | 0.6210 | 0.039* | |
C45 | 0.3903 (3) | 0.9291 (3) | 0.4435 (8) | 0.0285 (11) | |
H45A | 0.3689 | 0.9606 | 0.4330 | 0.034* | |
H45B | 0.4066 | 0.9241 | 0.3280 | 0.034* | |
C46 | 0.4579 (3) | 0.9657 (2) | 0.5708 (8) | 0.0195 (9) | |
H46A | 0.4963 | 1.0111 | 0.5196 | 0.023* | |
H46B | 0.4432 | 0.9775 | 0.6812 | 0.023* | |
O5 | 0.6443 (3) | 1.0874 (3) | 0.5006 (10) | 0.0193 (11) | 0.80 |
H5 | 0.6199 | 1.0367 | 0.5255 | 0.050* | 0.80 |
O5A | 0.6407 (16) | 1.0846 (16) | 0.555 (4) | 0.029 (7)* | 0.20 |
N5 | 0.7173 (2) | 1.1115 (2) | 0.5439 (7) | 0.0158 (7) | |
C51 | 0.7590 (2) | 1.1812 (2) | 0.5367 (7) | 0.0156 (8) | |
C52 | 0.7343 (3) | 1.2352 (3) | 0.4945 (9) | 0.0337 (12) | |
H52A | 0.6811 | 1.2107 | 0.5029 | 0.040* | |
H52B | 0.7479 | 1.2520 | 0.3745 | 0.040* | |
C53 | 0.7680 (4) | 1.3018 (3) | 0.6175 (10) | 0.0378 (14) | |
H53A | 0.7568 | 1.3386 | 0.5743 | 0.045* | |
H53B | 0.7465 | 1.2868 | 0.7335 | 0.045* | |
C54 | 0.8512 (3) | 1.3352 (3) | 0.6296 (8) | 0.0284 (11) | |
H54A | 0.8729 | 1.3532 | 0.5151 | 0.034* | |
H54B | 0.8712 | 1.3766 | 0.7099 | 0.034* | |
C55 | 0.8710 (3) | 1.2787 (3) | 0.6933 (9) | 0.0305 (11) | |
H55A | 0.8499 | 1.2609 | 0.8085 | 0.037* | |
H55B | 0.9240 | 1.3011 | 0.7025 | 0.037* | |
C56 | 0.8401 (3) | 1.2126 (3) | 0.5591 (9) | 0.0257 (10) | |
H56A | 0.8646 | 1.2297 | 0.4468 | 0.031* | |
H56B | 0.8499 | 1.1748 | 0.6022 | 0.031* | |
O6 | 0.7819 (3) | 1.0262 (3) | 0.5286 (12) | 0.0475 (17) | 0.80 |
H6 | 0.762 (3) | 1.049 (3) | 0.528 (8) | 0.025 (14)* | |
O6A | 0.7831 (6) | 1.0273 (6) | 0.6440 (17) | 0.002 (2)* | 0.20 |
N6 | 0.7299 (2) | 0.9523 (2) | 0.5757 (10) | 0.0320 (10) | |
C61 | 0.7556 (3) | 0.9090 (3) | 0.5699 (14) | 0.052 (2) | |
C62 | 0.8324 (4) | 0.9285 (5) | 0.5085 (15) | 0.050 (2) | 0.80 |
H62A | 0.8301 | 0.9158 | 0.3854 | 0.060* | 0.80 |
H62B | 0.8647 | 0.9813 | 0.5191 | 0.060* | 0.80 |
C62A | 0.8384 (9) | 0.9352 (9) | 0.651 (2) | 0.004 (3)* | 0.20 |
C63 | 0.8616 (5) | 0.8941 (5) | 0.599 (3) | 0.142 (8) | |
H63A | 0.8815 | 0.9208 | 0.7082 | 0.171* | |
H63B | 0.9027 | 0.8978 | 0.5324 | 0.171* | |
C64 | 0.8083 (5) | 0.8091 (5) | 0.6473 (16) | 0.055 (2) | 0.80 |
H64A | 0.8027 | 0.7791 | 0.5453 | 0.066* | 0.80 |
H64B | 0.8304 | 0.7950 | 0.7403 | 0.066* | 0.80 |
C64A | 0.8160 (8) | 0.8142 (9) | 0.517 (2) | 0.003 (3)* | 0.20 |
C65 | 0.7325 (5) | 0.7944 (4) | 0.7066 (13) | 0.0465 (19) | 0.80 |
H65A | 0.6990 | 0.7417 | 0.7126 | 0.056* | 0.80 |
H65B | 0.7363 | 0.8147 | 0.8230 | 0.056* | 0.80 |
C65A | 0.7387 (8) | 0.7964 (8) | 0.461 (2) | 0.001 (3)* | 0.20 |
C66 | 0.7033 (3) | 0.8280 (3) | 0.5829 (9) | 0.0286 (11) | |
H66A | 0.6558 | 0.8192 | 0.6237 | 0.034* | |
H66B | 0.6967 | 0.8056 | 0.4681 | 0.034* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0269 (17) | 0.0218 (16) | 0.0288 (17) | 0.0151 (14) | 0.0070 (14) | 0.0023 (13) |
N1 | 0.034 (2) | 0.030 (2) | 0.048 (3) | 0.017 (2) | 0.016 (2) | 0.014 (2) |
C1 | 0.028 (2) | 0.029 (3) | 0.023 (2) | 0.013 (2) | 0.0029 (18) | 0.0077 (18) |
C2 | 0.026 (2) | 0.023 (2) | 0.030 (2) | 0.0149 (19) | −0.0027 (18) | −0.0047 (18) |
C3 | 0.015 (2) | 0.023 (2) | 0.038 (3) | 0.0128 (18) | 0.0056 (18) | 0.0020 (19) |
C4 | 0.036 (3) | 0.018 (2) | 0.028 (2) | 0.020 (2) | 0.0010 (18) | −0.0010 (16) |
C5 | 0.045 (3) | 0.022 (2) | 0.052 (3) | 0.017 (2) | −0.021 (3) | −0.011 (2) |
C6 | 0.026 (3) | 0.036 (3) | 0.090 (6) | 0.016 (3) | −0.002 (3) | 0.007 (3) |
O2 | 0.030 (3) | 0.027 (3) | 0.063 (4) | 0.015 (2) | 0.001 (3) | 0.002 (3) |
N2 | 0.031 (3) | 0.026 (3) | 0.185 (10) | 0.016 (2) | 0.011 (4) | 0.012 (4) |
C22 | 0.034 (4) | 0.040 (4) | 0.065 (5) | 0.018 (3) | −0.002 (3) | −0.002 (4) |
C23 | 0.020 (3) | 0.020 (3) | 0.158 (9) | 0.004 (2) | 0.009 (4) | −0.020 (4) |
C24 | 0.020 (3) | 0.050 (5) | 0.261 (17) | 0.022 (3) | −0.005 (6) | −0.036 (7) |
C25 | 0.055 (5) | 0.072 (6) | 0.064 (6) | 0.039 (5) | −0.006 (4) | −0.021 (5) |
C26 | 0.036 (3) | 0.041 (4) | 0.092 (6) | 0.023 (3) | 0.014 (4) | 0.016 (4) |
C21 | 0.041 (4) | 0.039 (4) | 0.064 (6) | 0.020 (4) | 0.004 (4) | 0.002 (4) |
O3 | 0.0132 (18) | 0.0117 (17) | 0.0239 (19) | 0.0023 (14) | −0.0014 (14) | −0.0014 (14) |
N3 | 0.020 (2) | 0.022 (2) | 0.015 (2) | 0.013 (2) | 0.0033 (17) | −0.0025 (17) |
C31 | 0.018 (2) | 0.017 (2) | 0.0078 (19) | 0.009 (2) | 0.0034 (17) | −0.0029 (16) |
C32 | 0.015 (2) | 0.008 (2) | 0.016 (2) | 0.0043 (18) | −0.0041 (17) | 0.0005 (17) |
C33 | 0.029 (2) | 0.013 (2) | 0.032 (2) | 0.0110 (18) | 0.0015 (19) | −0.0010 (17) |
C34 | 0.010 (4) | 0.017 (3) | 0.036 (4) | −0.003 (3) | 0.002 (3) | −0.001 (2) |
C35 | 0.015 (3) | 0.027 (3) | 0.024 (3) | −0.002 (2) | −0.008 (2) | 0.010 (2) |
C36 | 0.025 (3) | 0.034 (3) | 0.055 (4) | 0.014 (2) | 0.001 (2) | 0.009 (3) |
O4 | 0.0212 (16) | 0.0299 (18) | 0.043 (2) | 0.0180 (15) | 0.0090 (14) | 0.0228 (16) |
N4 | 0.0180 (17) | 0.0137 (16) | 0.0104 (14) | 0.0079 (14) | −0.0011 (12) | 0.0032 (12) |
C41 | 0.0145 (18) | 0.0164 (19) | 0.0099 (16) | 0.0076 (16) | 0.0002 (13) | 0.0042 (13) |
C42 | 0.017 (2) | 0.021 (2) | 0.057 (3) | 0.0082 (19) | 0.007 (2) | 0.020 (2) |
C43 | 0.026 (3) | 0.037 (3) | 0.054 (3) | 0.013 (2) | −0.002 (2) | −0.002 (3) |
C44 | 0.027 (3) | 0.047 (3) | 0.029 (2) | 0.022 (2) | −0.0085 (19) | −0.006 (2) |
C45 | 0.029 (2) | 0.042 (3) | 0.024 (2) | 0.025 (2) | −0.0038 (18) | 0.0013 (19) |
C46 | 0.022 (2) | 0.018 (2) | 0.024 (2) | 0.0137 (18) | 0.0031 (17) | 0.0046 (16) |
O5 | 0.015 (2) | 0.014 (2) | 0.019 (3) | 0.0001 (16) | −0.0068 (19) | 0.0078 (18) |
N5 | 0.0158 (17) | 0.0143 (17) | 0.0157 (16) | 0.0062 (14) | 0.0025 (13) | 0.0002 (13) |
C51 | 0.0159 (19) | 0.0158 (19) | 0.0142 (18) | 0.0072 (16) | 0.0018 (15) | 0.0020 (14) |
C52 | 0.027 (3) | 0.019 (2) | 0.051 (3) | 0.008 (2) | −0.011 (2) | 0.001 (2) |
C53 | 0.037 (3) | 0.024 (3) | 0.046 (3) | 0.010 (2) | 0.015 (2) | −0.004 (2) |
C54 | 0.027 (2) | 0.025 (2) | 0.028 (2) | 0.009 (2) | 0.0003 (19) | −0.0081 (19) |
C55 | 0.019 (2) | 0.026 (2) | 0.038 (3) | 0.0051 (19) | −0.0085 (19) | −0.006 (2) |
C56 | 0.014 (2) | 0.021 (2) | 0.042 (3) | 0.0094 (18) | 0.0041 (19) | 0.008 (2) |
O6 | 0.025 (3) | 0.023 (2) | 0.091 (6) | 0.010 (2) | 0.010 (3) | 0.008 (3) |
N6 | 0.0128 (18) | 0.0164 (19) | 0.063 (3) | 0.0046 (15) | 0.0044 (19) | 0.0005 (19) |
C61 | 0.022 (3) | 0.019 (3) | 0.118 (7) | 0.012 (2) | 0.020 (3) | 0.013 (3) |
C62 | 0.032 (4) | 0.035 (4) | 0.084 (6) | 0.018 (3) | 0.014 (4) | 0.015 (4) |
C63 | 0.041 (5) | 0.039 (4) | 0.36 (3) | 0.026 (4) | −0.028 (8) | −0.028 (8) |
C64 | 0.053 (5) | 0.039 (4) | 0.078 (7) | 0.026 (4) | 0.000 (4) | 0.013 (4) |
C65 | 0.050 (4) | 0.031 (4) | 0.057 (5) | 0.019 (3) | −0.001 (4) | 0.002 (3) |
C66 | 0.025 (2) | 0.017 (2) | 0.040 (3) | 0.008 (2) | 0.007 (2) | 0.004 (2) |
Geometric parameters (Å, º) top
O1—N1 | 1.410 (6) | C34—C35 | 1.511 (12) |
N1—C1 | 1.287 (7) | C34A—C35A | 1.93 (6) |
C1—C2 | 1.493 (7) | C35—C36 | 1.503 (9) |
C1—C6 | 1.499 (8) | C35A—C36 | 1.12 (5) |
C2—C3 | 1.539 (6) | O4—N4 | 1.403 (5) |
C3—C4 | 1.537 (7) | N4—C41 | 1.268 (6) |
C4—C5 | 1.525 (8) | C41—C42 | 1.488 (6) |
C5—C6 | 1.488 (10) | C41—C46 | 1.501 (6) |
O2—N2 | 1.486 (9) | C42—C43 | 1.561 (8) |
O2A—N2 | 1.554 (12) | C43—C44 | 1.507 (9) |
N2—C21 | 1.336 (11) | C44—C45 | 1.492 (8) |
N2—C21A | 1.362 (17) | C45—C46 | 1.567 (7) |
C22—C23 | 1.407 (12) | O5—N5 | 1.391 (6) |
C22—C21 | 1.492 (11) | O5A—N5 | 1.42 (3) |
C22A—C23 | 1.291 (17) | N5—C51 | 1.276 (6) |
C22A—C21A | 1.54 (2) | C51—C56 | 1.497 (6) |
C23—C24 | 1.541 (10) | C51—C52 | 1.498 (7) |
C24—C25 | 1.570 (13) | C52—C53 | 1.532 (8) |
C24—C25A | 1.923 (19) | C53—C54 | 1.524 (8) |
C25—C26 | 1.425 (13) | C54—C55 | 1.519 (7) |
C25A—C26 | 1.359 (17) | C55—C56 | 1.579 (7) |
C26—C21A | 1.536 (17) | O6—N6 | 1.425 (7) |
C26—C21 | 1.538 (11) | O6A—N6 | 1.496 (12) |
O3—N3 | 1.413 (6) | N6—C61 | 1.267 (7) |
O3A—N3A | 1.46 (5) | C61—C66 | 1.496 (7) |
N3—C31 | 1.297 (8) | C61—C62 | 1.524 (9) |
N3A—C31A | 1.28 (6) | C61—C62A | 1.658 (17) |
C31—C32 | 1.495 (7) | C62—C63 | 1.351 (15) |
C31—C36 | 1.511 (8) | C62A—C63 | 1.250 (19) |
C31A—C32A | 1.69 (7) | C63—C64A | 1.584 (19) |
C31A—C36 | 1.77 (5) | C63—C64 | 1.603 (13) |
C32—C33 | 1.550 (6) | C64—C65 | 1.528 (13) |
C32A—C33 | 1.52 (5) | C64A—C65A | 1.53 (2) |
C33—C34A | 1.24 (4) | C65—C66 | 1.481 (10) |
C33—C34 | 1.561 (11) | C65A—C66 | 1.529 (15) |
| | | |
C1—N1—O1 | 112.7 (5) | C33—C34A—C35A | 109 (3) |
N1—C1—C2 | 126.1 (5) | C36—C35—C34 | 112.5 (5) |
N1—C1—C6 | 117.5 (5) | C36—C35A—C34A | 120 (4) |
C2—C1—C6 | 116.2 (5) | C35A—C36—C35 | 47 (2) |
C1—C2—C3 | 112.1 (4) | C35A—C36—C31 | 111 (2) |
C4—C3—C2 | 111.3 (4) | C35—C36—C31 | 111.8 (5) |
C5—C4—C3 | 109.7 (4) | C35A—C36—C31A | 120 (3) |
C6—C5—C4 | 111.0 (5) | C35—C36—C31A | 86.1 (18) |
C5—C6—C1 | 114.2 (5) | C31—C36—C31A | 45.5 (18) |
C21—N2—C21A | 37.5 (8) | C41—N4—O4 | 114.2 (3) |
C21—N2—O2 | 106.7 (7) | N4—C41—C42 | 125.7 (4) |
C21A—N2—O2 | 121.3 (8) | N4—C41—C46 | 117.7 (4) |
C21—N2—O2A | 115.6 (7) | C42—C41—C46 | 116.4 (4) |
C21A—N2—O2A | 99.8 (9) | C41—C42—C43 | 111.0 (5) |
O2—N2—O2A | 45.8 (5) | C44—C43—C42 | 111.2 (5) |
C23—C22—C21 | 114.1 (7) | C45—C44—C43 | 111.1 (5) |
C23—C22A—C21A | 122.3 (13) | C44—C45—C46 | 111.4 (4) |
C22A—C23—C22 | 62.2 (8) | C41—C46—C45 | 109.9 (4) |
C22A—C23—C24 | 108.4 (9) | C51—N5—O5 | 114.0 (4) |
C22—C23—C24 | 116.0 (8) | C51—N5—O5A | 116.8 (12) |
C23—C24—C25 | 108.1 (6) | O5—N5—O5A | 17.2 (10) |
C23—C24—C25A | 102.5 (8) | N5—C51—C56 | 118.5 (4) |
C25—C24—C25A | 54.2 (7) | N5—C51—C52 | 125.2 (4) |
C26—C25—C24 | 112.9 (9) | C56—C51—C52 | 116.1 (4) |
C26—C25A—C24 | 97.6 (10) | C51—C52—C53 | 112.5 (5) |
C25A—C26—C25 | 71.2 (8) | C54—C53—C52 | 110.9 (5) |
C25A—C26—C21A | 122.1 (10) | C55—C54—C53 | 111.0 (5) |
C25—C26—C21A | 96.6 (9) | C54—C55—C56 | 109.0 (4) |
C25A—C26—C21 | 99.4 (9) | C51—C56—C55 | 109.7 (4) |
C25—C26—C21 | 113.4 (7) | C61—N6—O6 | 113.7 (5) |
C21A—C26—C21 | 32.7 (7) | C61—N6—O6A | 113.9 (6) |
N2—C21—C22 | 127.0 (8) | O6—N6—O6A | 34.9 (5) |
N2—C21—C26 | 110.7 (7) | N6—C61—C66 | 118.6 (5) |
C22—C21—C26 | 119.5 (7) | N6—C61—C62 | 126.1 (6) |
N2—C21A—C26 | 109.4 (11) | C66—C61—C62 | 113.7 (5) |
N2—C21A—C22A | 127.7 (13) | N6—C61—C62A | 120.0 (8) |
C26—C21A—C22A | 113.2 (12) | C66—C61—C62A | 113.8 (7) |
C31—N3—O3 | 112.3 (4) | C62—C61—C62A | 40.0 (7) |
C31A—N3A—O3A | 111 (4) | C63—C62—C61 | 113.6 (9) |
N3—C31—C32 | 126.1 (5) | C63—C62A—C61 | 111.0 (12) |
N3—C31—C36 | 115.9 (5) | C62A—C63—C62 | 49.7 (9) |
C32—C31—C36 | 118.0 (5) | C62A—C63—C64A | 128.1 (11) |
N3A—C31A—C32A | 127 (5) | C62—C63—C64A | 99.6 (12) |
N3A—C31A—C36 | 109 (4) | C62A—C63—C64 | 113.6 (13) |
C32A—C31A—C36 | 112 (3) | C62—C63—C64 | 117.4 (8) |
C31—C32—C33 | 111.5 (4) | C64A—C63—C64 | 36.6 (7) |
C33—C32A—C31A | 111 (4) | C65—C64—C63 | 111.7 (7) |
C34A—C33—C32A | 111 (3) | C65A—C64A—C63 | 111.9 (11) |
C34A—C33—C32 | 116 (2) | C66—C65—C64 | 110.6 (7) |
C32A—C33—C32 | 79 (2) | C66—C65A—C64A | 114.2 (11) |
C34A—C33—C34 | 6 (2) | C65—C66—C61 | 109.9 (6) |
C32A—C33—C34 | 107 (2) | C65—C66—C65A | 76.9 (7) |
C32—C33—C34 | 110.2 (5) | C61—C66—C65A | 102.3 (7) |
C35—C34—C33 | 109.4 (6) | | |
Experimental details
| (jzs52) | (jzs51) | (3) |
Crystal data |
Chemical formula | C7H13NOS | C8H16N2O | C6H11NO |
Mr | 159.24 | 156.23 | 113.16 |
Crystal system, space group | Monoclinic, P121/c1 | Orthorhombic, Pbca | Trigonal, P3 |
Temperature (K) | 293 | 293 | 293 |
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), 90 | 90, 90, 90 | 90, 90, 120 |
V (Å3) | 861.4 (2) | 1838.8 (2) | 2905.88 (7) |
Z | 4 | 8 | 18 |
Radiation type | Mo Kα | Mo Kα | Mo Kα |
µ (mm−1) | 0.31 | 0.08 | 0.08 |
Crystal size (mm) | 0.30 × 0.20 × 0.20 | 0.40 × 0.25 × 0.10 | × × |
|
Data collection |
Diffractometer | Enraf-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)] |
Rint | 0.024 | ? | 0.031 |
(sin θ/λ)max (Å−1) | 0.606 | 0.605 | 0.650 |
|
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 reflections | 1602 | 1711 | 4440 |
No. of parameters | 92 | 103 | 496 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement | Riding | H atoms treated by a mixture of independent and constrained refinement |
(Δ/σ)max | < 0.001 | < 0.001 | 0.146 |
Δρmax, Δρmin (e Å−3) | 0.13, −0.20 | 0.13, −0.15 | 0.38, −1.14 |
Absolute structure | ? | ? | Flack H D (1983), Acta Cryst. A39, 876-881 |
Absolute structure parameter | ? | ? | 0 (10) |