Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807039918/er2029sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807039918/er2029Isup2.hkl |
CCDC reference: 663771
5.5 mmol picolinaldehyde was added to a solution of 5 mmol N-(2-aminocyclohexyl)-2,4,6-triisopropyl benzenesulfonamide in 30 ml e thanol. After stirring at room temperature for 4 h, the yellow precipitate was filtrated and washed with 10 ml e thanol. This compound was dried in vacuum and crystals grown from a solution of the title compound in acetonitrile.
H atoms were placed in calculated positions and refined using a riding model, with d(N—H) = 0.86 Å and Uiso(H) = 1.2Ueq(N), d(C—H) = 0.93 Å and Uiso(H) = 1.2Ueq(C) for Csp2, d(C—H) = 0.97 Å and Uiso(H) = 1.2Ueq(C) for the methylene groups, and d(C—H) = 0.96 Å and Uiso(H) = 1.5Ueq(C) for the methyl groups. The three H atoms of the acetonitrile solvate molecules were not located. The value of the Flack parameter is meaningless because of its large s.u. value thus the Friedel equivalents were merged in the final refinements.
In past two decade, significant advances have been made in polymerization of cyclic ester, such as poly(ε-caprolactone) (Endo et al., 1987), poly(lactide) (Chamberlain et al., 1999). The title compound (I), is designed as catalyst ligand for polymerization of poly(lactide). This ligand is one charge bulky shiff base after deprotonation, this kind of ligand is very useful in the ring-opening polymerization of cyclic esters (Cabaret et al., 2004). In the present study, the bulky shiff base ligand derived from the condensation of picolinaldehyde and N-(2-aminocyclohexyl)-2,4,6-triisopropyl benzenesulfonamide in ethanol, was synthesized for the investigation of its application in the Ring-Opening polymerization of cyclic esters.
The geometric parameters for (I) are normal (Fig. 1). The compound is a dimer with an intermolecular N3—H3A–N1 hydrogen bond (Fig. 2).
For related literature, see: Cabaret et al. (2004); Chamberlain et al. (1999); Endo et al. (1987).
Data collection: SMART (Bruker, 1999); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Sheldrick, 2000); software used to prepare material for publication: SHELXTL.
C27H39N3O2S·0.5C2H3N | Dx = 1.117 Mg m−3 |
Mr = 488.70 | Mo Kα radiation, λ = 0.71073 Å |
Tetragonal, I41/a | Cell parameters from 6978 reflections |
Hall symbol: -I 4ad | θ = 2.2–22.8° |
a = 21.9895 (17) Å | µ = 0.14 mm−1 |
c = 24.035 (3) Å | T = 293 K |
V = 11622.0 (18) Å3 | Block, yellow |
Z = 16 | 0.30 × 0.28 × 0.20 mm |
F(000) = 4216 |
Bruker SMART 1K CCD area-detector diffractometer | 5766 independent reflections |
Radiation source: fine-focus sealed tube | 3108 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.063 |
Detector resolution: 10 pixels mm-1 | θmax = 26.1°, θmin = 1.9° |
φ and ω scans | h = −17→27 |
Absorption correction: multi-scan (SADABS; Sheldrick, 2002) | k = −27→26 |
Tmin = 0.769, Tmax = 1.000 | l = −29→29 |
31641 measured reflections |
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)] = 0.062 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.216 | H-atom parameters constrained |
S = 1.04 | w = 1/[σ2(Fo2) + (0.1113P)2 + 3.0566P] where P = (Fo2 + 2Fc2)/3 |
5766 reflections | (Δ/σ)max < 0.001 |
313 parameters | Δρmax = 0.28 e Å−3 |
0 restraints | Δρmin = −0.33 e Å−3 |
C27H39N3O2S·0.5C2H3N | Z = 16 |
Mr = 488.70 | Mo Kα radiation |
Tetragonal, I41/a | µ = 0.14 mm−1 |
a = 21.9895 (17) Å | T = 293 K |
c = 24.035 (3) Å | 0.30 × 0.28 × 0.20 mm |
V = 11622.0 (18) Å3 |
Bruker SMART 1K CCD area-detector diffractometer | 5766 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 2002) | 3108 reflections with I > 2σ(I) |
Tmin = 0.769, Tmax = 1.000 | Rint = 0.063 |
31641 measured reflections |
R[F2 > 2σ(F2)] = 0.062 | 0 restraints |
wR(F2) = 0.216 | H-atom parameters constrained |
S = 1.04 | Δρmax = 0.28 e Å−3 |
5766 reflections | Δρmin = −0.33 e Å−3 |
313 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
S1 | 0.12749 (4) | 0.60119 (4) | 0.03742 (3) | 0.0730 (3) | |
O1 | 0.14047 (12) | 0.57455 (12) | −0.01578 (8) | 0.0999 (8) | |
O2 | 0.09863 (11) | 0.65909 (10) | 0.03769 (10) | 0.0917 (7) | |
C1 | −0.07243 (18) | 0.68154 (17) | −0.01539 (14) | 0.0931 (11) | |
H1 | −0.0586 | 0.7005 | 0.0168 | 0.112* | |
N2 | −0.03673 (11) | 0.60214 (11) | 0.07332 (10) | 0.0693 (7) | |
N3 | 0.08473 (11) | 0.55429 (11) | 0.06978 (9) | 0.0688 (6) | |
H3A | 0.0798 | 0.5186 | 0.0559 | 0.083* | |
N4 | 0.0000 | 0.7500 | 0.2299 (5) | 0.265 (6) | |
N1 | −0.09302 (12) | 0.59030 (12) | −0.06422 (11) | 0.0794 (7) | |
C4 | −0.11168 (15) | 0.62558 (18) | −0.10696 (13) | 0.0843 (9) | |
H4 | −0.1257 | 0.6064 | −0.1390 | 0.101* | |
C3 | −0.11121 (16) | 0.68721 (18) | −0.10611 (15) | 0.0890 (10) | |
H3B | −0.1242 | 0.7093 | −0.1369 | 0.107* | |
C2 | −0.09163 (19) | 0.71601 (18) | −0.05998 (16) | 0.1019 (12) | |
H2 | −0.0911 | 0.7583 | −0.0582 | 0.122* | |
C5 | −0.07375 (13) | 0.61963 (14) | −0.01864 (12) | 0.0687 (8) | |
C6 | −0.05335 (13) | 0.58042 (15) | 0.02798 (12) | 0.0715 (8) | |
H6A | −0.0530 | 0.5385 | 0.0232 | 0.086* | |
C7 | −0.01480 (13) | 0.56002 (14) | 0.11595 (11) | 0.0676 (8) | |
H7A | −0.0233 | 0.5181 | 0.1046 | 0.081* | |
C8 | −0.04702 (16) | 0.57368 (19) | 0.17042 (14) | 0.0940 (11) | |
H8A | −0.0418 | 0.6163 | 0.1795 | 0.113* | |
H8B | −0.0902 | 0.5660 | 0.1661 | 0.113* | |
C9 | −0.02260 (19) | 0.5352 (2) | 0.21751 (14) | 0.1026 (12) | |
H9A | −0.0432 | 0.5458 | 0.2518 | 0.123* | |
H9B | −0.0304 | 0.4926 | 0.2098 | 0.123* | |
C10 | 0.0446 (2) | 0.5451 (2) | 0.22403 (13) | 0.1036 (12) | |
H10A | 0.0600 | 0.5187 | 0.2531 | 0.124* | |
H10B | 0.0520 | 0.5869 | 0.2353 | 0.124* | |
C11 | 0.07834 (16) | 0.53241 (18) | 0.17040 (13) | 0.0898 (10) | |
H11A | 0.0752 | 0.4894 | 0.1618 | 0.108* | |
H11B | 0.1210 | 0.5420 | 0.1754 | 0.108* | |
C12 | 0.05348 (13) | 0.56906 (13) | 0.12206 (11) | 0.0633 (7) | |
H12A | 0.0607 | 0.6122 | 0.1300 | 0.076* | |
C13 | 0.19802 (13) | 0.60672 (14) | 0.07480 (11) | 0.0660 (7) | |
C14 | 0.24248 (16) | 0.56126 (15) | 0.06689 (13) | 0.0758 (8) | |
C15 | 0.23114 (18) | 0.50094 (16) | 0.03670 (16) | 0.0942 (11) | |
H15A | 0.1873 | 0.4977 | 0.0298 | 0.113* | |
C16 | 0.2634 (3) | 0.5001 (2) | −0.0199 (2) | 0.160 (2) | |
H16A | 0.2503 | 0.5343 | −0.0416 | 0.240* | |
H16B | 0.2536 | 0.4632 | −0.0392 | 0.240* | |
H16C | 0.3066 | 0.5023 | −0.0144 | 0.240* | |
C17 | 0.2495 (2) | 0.44733 (19) | 0.0724 (3) | 0.145 (2) | |
H17A | 0.2279 | 0.4488 | 0.1070 | 0.217* | |
H17B | 0.2925 | 0.4490 | 0.0794 | 0.217* | |
H17C | 0.2399 | 0.4102 | 0.0533 | 0.217* | |
C18 | 0.29944 (17) | 0.57050 (17) | 0.08867 (15) | 0.0882 (10) | |
H18A | 0.3291 | 0.5413 | 0.0819 | 0.106* | |
C19 | 0.31504 (17) | 0.62005 (19) | 0.11959 (16) | 0.0926 (10) | |
C20 | 0.3802 (2) | 0.6297 (3) | 0.1408 (3) | 0.1416 (18) | |
H20A | 0.3949 | 0.5879 | 0.1455 | 0.170* | |
C21 | 0.3848 (3) | 0.6544 (3) | 0.1970 (2) | 0.174 (2) | |
H21A | 0.4269 | 0.6584 | 0.2070 | 0.261* | |
H21B | 0.3649 | 0.6276 | 0.2227 | 0.261* | |
H21C | 0.3656 | 0.6937 | 0.1982 | 0.261* | |
C22 | 0.4194 (3) | 0.6531 (5) | 0.0965 (3) | 0.241 (5) | |
H22A | 0.4599 | 0.6586 | 0.1106 | 0.362* | |
H22B | 0.4040 | 0.6914 | 0.0836 | 0.362* | |
H22C | 0.4202 | 0.6247 | 0.0661 | 0.362* | |
C23 | 0.27044 (17) | 0.66180 (17) | 0.13025 (14) | 0.0859 (10) | |
H23A | 0.2799 | 0.6951 | 0.1525 | 0.103* | |
C24 | 0.21147 (15) | 0.65686 (14) | 0.10948 (12) | 0.0742 (8) | |
C25 | 0.16786 (18) | 0.70501 (17) | 0.13004 (16) | 0.0975 (11) | |
H25A | 0.1272 | 0.6927 | 0.1178 | 0.117* | |
C26 | 0.1808 (2) | 0.7662 (2) | 0.1032 (2) | 0.1426 (18) | |
H26A | 0.1788 | 0.7623 | 0.0634 | 0.214* | |
H26B | 0.2206 | 0.7798 | 0.1138 | 0.214* | |
H26C | 0.1511 | 0.7953 | 0.1154 | 0.214* | |
C27 | 0.1664 (3) | 0.7066 (3) | 0.1933 (2) | 0.168 (2) | |
H27A | 0.1567 | 0.6668 | 0.2073 | 0.252* | |
H27B | 0.1361 | 0.7350 | 0.2055 | 0.252* | |
H27C | 0.2055 | 0.7188 | 0.2071 | 0.252* | |
C28 | 0.0000 | 0.7500 | 0.1224 (3) | 0.1063 (17) | |
C29 | 0.0000 | 0.7500 | 0.1818 (6) | 0.153 (3) |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0865 (6) | 0.0789 (5) | 0.0537 (4) | 0.0073 (4) | 0.0018 (4) | 0.0124 (4) |
O1 | 0.133 (2) | 0.1216 (19) | 0.0456 (12) | 0.0107 (16) | 0.0040 (12) | 0.0053 (11) |
O2 | 0.1019 (16) | 0.0725 (14) | 0.1008 (17) | 0.0140 (12) | −0.0035 (13) | 0.0284 (12) |
C1 | 0.123 (3) | 0.082 (2) | 0.074 (2) | 0.002 (2) | −0.019 (2) | 0.0050 (18) |
N2 | 0.0696 (15) | 0.0797 (16) | 0.0586 (14) | −0.0029 (12) | −0.0122 (11) | 0.0093 (12) |
N3 | 0.0828 (16) | 0.0666 (14) | 0.0572 (13) | −0.0009 (12) | 0.0009 (12) | 0.0025 (11) |
N4 | 0.251 (12) | 0.356 (16) | 0.188 (10) | −0.023 (10) | 0.000 | 0.000 |
N1 | 0.0896 (18) | 0.0865 (17) | 0.0620 (15) | 0.0000 (14) | −0.0183 (13) | 0.0053 (13) |
C4 | 0.092 (2) | 0.103 (3) | 0.0588 (19) | 0.0096 (19) | −0.0131 (16) | 0.0068 (17) |
C3 | 0.094 (2) | 0.100 (3) | 0.073 (2) | 0.016 (2) | −0.0032 (19) | 0.026 (2) |
C2 | 0.137 (3) | 0.087 (2) | 0.082 (2) | 0.011 (2) | −0.022 (2) | 0.010 (2) |
C5 | 0.0682 (18) | 0.079 (2) | 0.0588 (17) | 0.0029 (15) | −0.0073 (14) | 0.0069 (14) |
C6 | 0.0725 (19) | 0.0752 (19) | 0.0668 (19) | −0.0061 (15) | −0.0134 (15) | 0.0092 (15) |
C7 | 0.0730 (18) | 0.0712 (18) | 0.0586 (16) | −0.0110 (15) | −0.0134 (14) | 0.0113 (14) |
C8 | 0.083 (2) | 0.122 (3) | 0.077 (2) | −0.001 (2) | 0.0104 (18) | 0.026 (2) |
C9 | 0.119 (3) | 0.124 (3) | 0.064 (2) | 0.000 (2) | 0.014 (2) | 0.025 (2) |
C10 | 0.129 (3) | 0.132 (3) | 0.0504 (18) | 0.004 (3) | −0.0170 (19) | 0.0176 (19) |
C11 | 0.090 (2) | 0.117 (3) | 0.0625 (19) | 0.016 (2) | −0.0151 (17) | 0.0133 (18) |
C12 | 0.0727 (18) | 0.0670 (17) | 0.0501 (15) | −0.0021 (14) | −0.0073 (13) | 0.0026 (13) |
C13 | 0.0754 (18) | 0.0720 (18) | 0.0506 (15) | 0.0039 (15) | 0.0152 (13) | 0.0044 (13) |
C14 | 0.082 (2) | 0.077 (2) | 0.0688 (18) | 0.0065 (17) | 0.0151 (16) | 0.0061 (15) |
C15 | 0.097 (2) | 0.077 (2) | 0.108 (3) | 0.0118 (19) | 0.024 (2) | −0.012 (2) |
C16 | 0.190 (5) | 0.142 (4) | 0.147 (4) | −0.025 (4) | 0.085 (4) | −0.058 (3) |
C17 | 0.125 (4) | 0.076 (3) | 0.233 (6) | 0.007 (2) | −0.018 (4) | 0.014 (3) |
C18 | 0.078 (2) | 0.095 (3) | 0.091 (2) | 0.0136 (19) | 0.0080 (19) | 0.003 (2) |
C19 | 0.083 (2) | 0.105 (3) | 0.090 (2) | −0.001 (2) | −0.0008 (19) | 0.006 (2) |
C20 | 0.101 (3) | 0.174 (5) | 0.149 (5) | −0.005 (3) | −0.021 (3) | −0.026 (4) |
C21 | 0.163 (5) | 0.246 (7) | 0.114 (4) | −0.020 (5) | −0.046 (4) | 0.013 (5) |
C22 | 0.096 (4) | 0.447 (14) | 0.181 (7) | −0.063 (6) | 0.010 (4) | −0.069 (8) |
C23 | 0.089 (2) | 0.094 (2) | 0.075 (2) | −0.009 (2) | 0.0057 (18) | −0.0062 (18) |
C24 | 0.082 (2) | 0.078 (2) | 0.0624 (18) | 0.0012 (16) | 0.0182 (16) | 0.0027 (15) |
C25 | 0.092 (2) | 0.095 (3) | 0.105 (3) | 0.000 (2) | 0.023 (2) | −0.026 (2) |
C26 | 0.129 (4) | 0.089 (3) | 0.210 (5) | 0.017 (3) | 0.030 (4) | −0.009 (3) |
C27 | 0.181 (5) | 0.198 (5) | 0.125 (4) | 0.016 (4) | 0.055 (4) | −0.066 (4) |
C28 | 0.115 (4) | 0.099 (4) | 0.105 (4) | 0.019 (3) | 0.000 | 0.000 |
C29 | 0.139 (7) | 0.137 (6) | 0.184 (10) | −0.001 (5) | 0.000 | 0.000 |
S1—O2 | 1.423 (2) | C13—C24 | 1.414 (4) |
S1—O1 | 1.435 (2) | C14—C18 | 1.373 (5) |
S1—N3 | 1.598 (2) | C14—C15 | 1.532 (5) |
S1—C13 | 1.796 (3) | C15—C17 | 1.512 (6) |
C1—C5 | 1.364 (5) | C15—C16 | 1.536 (5) |
C1—C2 | 1.379 (5) | C15—H15A | 0.9800 |
C1—H1 | 0.9300 | C16—H16A | 0.9600 |
N2—C6 | 1.245 (4) | C16—H16B | 0.9600 |
N2—C7 | 1.463 (3) | C16—H16C | 0.9600 |
N3—C12 | 1.469 (3) | C17—H17A | 0.9600 |
N3—H3A | 0.8600 | C17—H17B | 0.9600 |
N4—C29 | 1.157 (12) | C17—H17C | 0.9600 |
N1—C5 | 1.340 (4) | C18—C19 | 1.363 (5) |
N1—C4 | 1.351 (4) | C18—H18A | 0.9300 |
C4—C3 | 1.356 (5) | C19—C23 | 1.367 (5) |
C4—H4 | 0.9300 | C19—C20 | 1.535 (6) |
C3—C2 | 1.347 (5) | C20—C21 | 1.460 (7) |
C3—H3B | 0.9300 | C20—C22 | 1.465 (8) |
C2—H2 | 0.9300 | C20—H20A | 0.9800 |
C5—C6 | 1.483 (4) | C21—H21A | 0.9600 |
C6—H6A | 0.9300 | C21—H21B | 0.9600 |
C7—C8 | 1.518 (4) | C21—H21C | 0.9600 |
C7—C12 | 1.522 (4) | C22—H22A | 0.9600 |
C7—H7A | 0.9800 | C22—H22B | 0.9600 |
C8—C9 | 1.512 (5) | C22—H22C | 0.9600 |
C8—H8A | 0.9700 | C23—C24 | 1.394 (5) |
C8—H8B | 0.9700 | C23—H23A | 0.9300 |
C9—C10 | 1.503 (5) | C24—C25 | 1.512 (5) |
C9—H9A | 0.9700 | C25—C26 | 1.520 (6) |
C9—H9B | 0.9700 | C25—C27 | 1.522 (6) |
C10—C11 | 1.513 (5) | C25—H25A | 0.9800 |
C10—H10A | 0.9700 | C26—H26A | 0.9600 |
C10—H10B | 0.9700 | C26—H26B | 0.9600 |
C11—C12 | 1.516 (4) | C26—H26C | 0.9600 |
C11—H11A | 0.9700 | C27—H27A | 0.9600 |
C11—H11B | 0.9700 | C27—H27B | 0.9600 |
C12—H12A | 0.9800 | C27—H27C | 0.9600 |
C13—C14 | 1.411 (4) | C28—C29 | 1.427 (13) |
O2—S1—O1 | 117.26 (14) | C18—C14—C15 | 117.2 (3) |
O2—S1—N3 | 108.23 (14) | C13—C14—C15 | 124.4 (3) |
O1—S1—N3 | 106.69 (14) | C17—C15—C14 | 111.3 (4) |
O2—S1—C13 | 108.81 (15) | C17—C15—C16 | 111.7 (4) |
O1—S1—C13 | 107.55 (14) | C14—C15—C16 | 110.8 (3) |
N3—S1—C13 | 107.96 (13) | C17—C15—H15A | 107.6 |
C5—C1—C2 | 119.8 (3) | C14—C15—H15A | 107.6 |
C5—C1—H1 | 120.1 | C16—C15—H15A | 107.6 |
C2—C1—H1 | 120.1 | C15—C16—H16A | 109.5 |
C6—N2—C7 | 117.8 (3) | C15—C16—H16B | 109.5 |
C12—N3—S1 | 123.3 (2) | H16A—C16—H16B | 109.5 |
C12—N3—H3A | 118.3 | C15—C16—H16C | 109.5 |
S1—N3—H3A | 118.3 | H16A—C16—H16C | 109.5 |
C5—N1—C4 | 116.2 (3) | H16B—C16—H16C | 109.5 |
N1—C4—C3 | 124.1 (3) | C15—C17—H17A | 109.5 |
N1—C4—H4 | 118.0 | C15—C17—H17B | 109.5 |
C3—C4—H4 | 118.0 | H17A—C17—H17B | 109.5 |
C2—C3—C4 | 119.0 (3) | C15—C17—H17C | 109.5 |
C2—C3—H3B | 120.5 | H17A—C17—H17C | 109.5 |
C4—C3—H3B | 120.5 | H17B—C17—H17C | 109.5 |
C3—C2—C1 | 118.6 (4) | C19—C18—C14 | 123.8 (3) |
C3—C2—H2 | 120.7 | C19—C18—H18A | 118.1 |
C1—C2—H2 | 120.7 | C14—C18—H18A | 118.1 |
N1—C5—C1 | 122.3 (3) | C18—C19—C23 | 117.3 (3) |
N1—C5—C6 | 115.7 (3) | C18—C19—C20 | 121.7 (4) |
C1—C5—C6 | 122.0 (3) | C23—C19—C20 | 121.0 (4) |
N2—C6—C5 | 121.8 (3) | C21—C20—C22 | 120.0 (5) |
N2—C6—H6A | 119.1 | C21—C20—C19 | 115.1 (5) |
C5—C6—H6A | 119.1 | C22—C20—C19 | 110.9 (5) |
N2—C7—C8 | 109.0 (3) | C21—C20—H20A | 102.6 |
N2—C7—C12 | 108.1 (2) | C22—C20—H20A | 102.6 |
C8—C7—C12 | 110.6 (2) | C19—C20—H20A | 102.6 |
N2—C7—H7A | 109.7 | C20—C21—H21A | 109.5 |
C8—C7—H7A | 109.7 | C20—C21—H21B | 109.5 |
C12—C7—H7A | 109.7 | H21A—C21—H21B | 109.5 |
C9—C8—C7 | 111.6 (3) | C20—C21—H21C | 109.5 |
C9—C8—H8A | 109.3 | H21A—C21—H21C | 109.5 |
C7—C8—H8A | 109.3 | H21B—C21—H21C | 109.5 |
C9—C8—H8B | 109.3 | C20—C22—H22A | 109.5 |
C7—C8—H8B | 109.3 | C20—C22—H22B | 109.5 |
H8A—C8—H8B | 108.0 | H22A—C22—H22B | 109.5 |
C10—C9—C8 | 110.2 (3) | C20—C22—H22C | 109.5 |
C10—C9—H9A | 109.6 | H22A—C22—H22C | 109.5 |
C8—C9—H9A | 109.6 | H22B—C22—H22C | 109.5 |
C10—C9—H9B | 109.6 | C19—C23—C24 | 123.2 (3) |
C8—C9—H9B | 109.6 | C19—C23—H23A | 118.4 |
H9A—C9—H9B | 108.1 | C24—C23—H23A | 118.4 |
C9—C10—C11 | 111.5 (3) | C23—C24—C13 | 117.8 (3) |
C9—C10—H10A | 109.3 | C23—C24—C25 | 114.7 (3) |
C11—C10—H10A | 109.3 | C13—C24—C25 | 127.3 (3) |
C9—C10—H10B | 109.3 | C24—C25—C26 | 111.3 (3) |
C11—C10—H10B | 109.3 | C24—C25—C27 | 110.8 (4) |
H10A—C10—H10B | 108.0 | C26—C25—C27 | 114.1 (4) |
C10—C11—C12 | 112.2 (3) | C24—C25—H25A | 106.7 |
C10—C11—H11A | 109.2 | C26—C25—H25A | 106.7 |
C12—C11—H11A | 109.2 | C27—C25—H25A | 106.7 |
C10—C11—H11B | 109.2 | C25—C26—H26A | 109.5 |
C12—C11—H11B | 109.2 | C25—C26—H26B | 109.5 |
H11A—C11—H11B | 107.9 | H26A—C26—H26B | 109.5 |
N3—C12—C11 | 111.7 (2) | C25—C26—H26C | 109.5 |
N3—C12—C7 | 110.5 (2) | H26A—C26—H26C | 109.5 |
C11—C12—C7 | 111.1 (2) | H26B—C26—H26C | 109.5 |
N3—C12—H12A | 107.8 | C25—C27—H27A | 109.5 |
C11—C12—H12A | 107.8 | C25—C27—H27B | 109.5 |
C7—C12—H12A | 107.8 | H27A—C27—H27B | 109.5 |
C14—C13—C24 | 119.1 (3) | C25—C27—H27C | 109.5 |
C14—C13—S1 | 118.9 (2) | H27A—C27—H27C | 109.5 |
C24—C13—S1 | 121.9 (2) | H27B—C27—H27C | 109.5 |
C18—C14—C13 | 118.4 (3) | N4—C29—C28 | 180.000 (3) |
O2—S1—N3—C12 | −42.8 (3) | O2—S1—C13—C24 | 14.6 (3) |
O1—S1—N3—C12 | −169.8 (2) | O1—S1—C13—C24 | 142.6 (2) |
C13—S1—N3—C12 | 74.8 (2) | N3—S1—C13—C24 | −102.6 (2) |
C5—N1—C4—C3 | 0.7 (5) | C24—C13—C14—C18 | −6.5 (4) |
N1—C4—C3—C2 | −0.7 (6) | S1—C13—C14—C18 | 170.1 (2) |
C4—C3—C2—C1 | 0.4 (6) | C24—C13—C14—C15 | 171.8 (3) |
C5—C1—C2—C3 | −0.2 (6) | S1—C13—C14—C15 | −11.6 (4) |
C4—N1—C5—C1 | −0.5 (5) | C18—C14—C15—C17 | 52.0 (4) |
C4—N1—C5—C6 | −180.0 (3) | C13—C14—C15—C17 | −126.4 (4) |
C2—C1—C5—N1 | 0.3 (6) | C18—C14—C15—C16 | −72.9 (5) |
C2—C1—C5—C6 | 179.7 (3) | C13—C14—C15—C16 | 108.7 (4) |
C7—N2—C6—C5 | −177.3 (3) | C13—C14—C18—C19 | 2.8 (5) |
N1—C5—C6—N2 | −177.1 (3) | C15—C14—C18—C19 | −175.6 (3) |
C1—C5—C6—N2 | 3.5 (5) | C14—C18—C19—C23 | 1.6 (6) |
C6—N2—C7—C8 | −130.4 (3) | C14—C18—C19—C20 | −177.2 (4) |
C6—N2—C7—C12 | 109.4 (3) | C18—C19—C20—C21 | −140.9 (5) |
N2—C7—C8—C9 | −175.2 (3) | C23—C19—C20—C21 | 40.4 (7) |
C12—C7—C8—C9 | −56.6 (4) | C18—C19—C20—C22 | 78.8 (7) |
C7—C8—C9—C10 | 57.6 (4) | C23—C19—C20—C22 | −100.0 (6) |
C8—C9—C10—C11 | −56.1 (5) | C18—C19—C23—C24 | −2.4 (5) |
C9—C10—C11—C12 | 54.9 (5) | C20—C19—C23—C24 | 176.5 (4) |
S1—N3—C12—C11 | −112.8 (3) | C19—C23—C24—C13 | −1.4 (5) |
S1—N3—C12—C7 | 122.9 (2) | C19—C23—C24—C25 | 175.2 (3) |
C10—C11—C12—N3 | −177.4 (3) | C14—C13—C24—C23 | 5.8 (4) |
C10—C11—C12—C7 | −53.5 (4) | S1—C13—C24—C23 | −170.7 (2) |
N2—C7—C12—N3 | −62.3 (3) | C14—C13—C24—C25 | −170.3 (3) |
C8—C7—C12—N3 | 178.5 (3) | S1—C13—C24—C25 | 13.2 (4) |
N2—C7—C12—C11 | 173.1 (2) | C23—C24—C25—C26 | 73.3 (4) |
C8—C7—C12—C11 | 54.0 (3) | C13—C24—C25—C26 | −110.5 (4) |
O2—S1—C13—C14 | −161.9 (2) | C23—C24—C25—C27 | −54.8 (5) |
O1—S1—C13—C14 | −34.0 (3) | C13—C24—C25—C27 | 121.4 (4) |
N3—S1—C13—C14 | 80.8 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3A···N1i | 0.86 | 2.42 | 3.188 (4) | 149 |
Symmetry code: (i) −x, −y+1, −z. |
Experimental details
Crystal data | |
Chemical formula | C27H39N3O2S·0.5C2H3N |
Mr | 488.70 |
Crystal system, space group | Tetragonal, I41/a |
Temperature (K) | 293 |
a, c (Å) | 21.9895 (17), 24.035 (3) |
V (Å3) | 11622.0 (18) |
Z | 16 |
Radiation type | Mo Kα |
µ (mm−1) | 0.14 |
Crystal size (mm) | 0.30 × 0.28 × 0.20 |
Data collection | |
Diffractometer | Bruker SMART 1K CCD area-detector |
Absorption correction | Multi-scan (SADABS; Sheldrick, 2002) |
Tmin, Tmax | 0.769, 1.000 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 31641, 5766, 3108 |
Rint | 0.063 |
(sin θ/λ)max (Å−1) | 0.619 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.062, 0.216, 1.04 |
No. of reflections | 5766 |
No. of parameters | 313 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.28, −0.33 |
Computer programs: SMART (Bruker, 1999), SAINT (Bruker, 1999), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Sheldrick, 2000), SHELXTL.
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3A···N1i | 0.86 | 2.42 | 3.188 (4) | 148.8 |
Symmetry code: (i) −x, −y+1, −z. |
In past two decade, significant advances have been made in polymerization of cyclic ester, such as poly(ε-caprolactone) (Endo et al., 1987), poly(lactide) (Chamberlain et al., 1999). The title compound (I), is designed as catalyst ligand for polymerization of poly(lactide). This ligand is one charge bulky shiff base after deprotonation, this kind of ligand is very useful in the ring-opening polymerization of cyclic esters (Cabaret et al., 2004). In the present study, the bulky shiff base ligand derived from the condensation of picolinaldehyde and N-(2-aminocyclohexyl)-2,4,6-triisopropyl benzenesulfonamide in ethanol, was synthesized for the investigation of its application in the Ring-Opening polymerization of cyclic esters.
The geometric parameters for (I) are normal (Fig. 1). The compound is a dimer with an intermolecular N3—H3A–N1 hydrogen bond (Fig. 2).