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The title compound, C27H39N3O2S·0.5CH3CN, a Schiff base ligand, was synthesized by the condensation of picolin­aldehyde and N-(2-amino­cyclo­hexyl)-2,4,6-triisopropyl­benzene­sulfonamide in ethanol. Crystals were grown from an acetonitrile solution. The cyclohexane ring has a chair conformation and the dihedral angle between the pyridine and benzene rings is 55.6°. The mol­ecules form dimers via N—H...N hydrogen bonds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807039918/er2029sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807039918/er2029Isup2.hkl
Contains datablock I

CCDC reference: 663771

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.006 Å
  • H-atom completeness 97%
  • R factor = 0.062
  • wR factor = 0.216
  • Data-to-parameter ratio = 18.4

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT220_ALERT_2_B Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.81 Ratio PLAT222_ALERT_3_B Large Non-Solvent H Ueq(max)/Ueq(min) ... 4.76 Ratio PLAT242_ALERT_2_B Check Low Ueq as Compared to Neighbors for C15 PLAT242_ALERT_2_B Check Low Ueq as Compared to Neighbors for C25
Alert level C ABSTM02_ALERT_3_C The ratio of expected to reported Tmax/Tmin(RR') is < 0.90 Tmin and Tmax reported: 0.769 1.000 Tmin(prime) and Tmax expected: 0.958 0.973 RR(prime) = 0.781 Please check that your absorption correction is appropriate. CHEMW01_ALERT_1_C The difference between the given and expected weight for compound is greater 1 mass unit. Check that all hydrogen atoms have been taken into account. PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings Differ .... ? PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT045_ALERT_1_C Calculated and Reported Z Differ by ............ 0.50 Ratio PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large ............. 0.78 PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.97 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C20 PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for C29 PLAT321_ALERT_2_C Check Hybridisation of C28 in Solvent/Ion .. ? PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 6
Alert level G FORMU01_ALERT_2_G There is a discrepancy between the atom counts in the _chemical_formula_sum and the formula from the _atom_site* data. Atom count from _chemical_formula_sum:C28 H40.5 N3.5 O2 S1 Atom count from the _atom_site data: C28 H39 N3.5 O2 S1 ABSTM02_ALERT_3_G When printed, the submitted absorption T values will be replaced by the scaled T values. Since the ratio of scaled T's is identical to the ratio of reported T values, the scaling does not imply a change to the absorption corrections used in the study. Ratio of Tmax expected/reported 0.973 Tmax scaled 0.973 Tmin scaled 0.748 CELLZ01_ALERT_1_G Difference between formula and atom_site contents detected. CELLZ01_ALERT_1_G WARNING: H atoms missing from atom site list. Is this intentional? From the CIF: _cell_formula_units_Z 16 From the CIF: _chemical_formula_sum C28 H40.5 N3.5 O2 S1 TEST: Compare cell contents of formula and atom_site data atom Z*formula cif sites diff C 448.00 448.00 0.00 H 648.00 624.00 24.00 N 56.00 56.00 0.00 O 32.00 32.00 0.00 S 16.00 16.00 0.00 PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K PLAT793_ALERT_1_G Check the Absolute Configuration of C7 = ... R PLAT793_ALERT_1_G Check the Absolute Configuration of C12 = ... R
0 ALERT level A = In general: serious problem 4 ALERT level B = Potentially serious problem 11 ALERT level C = Check and explain 8 ALERT level G = General alerts; check 10 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 6 ALERT type 2 Indicator that the structure model may be wrong or deficient 5 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Comment top

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).

Related literature top

For related literature, see: Cabaret et al. (2004); Chamberlain et al. (1999); Endo et al. (1987).

Experimental top

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.

Refinement top

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.

Structure description top

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).

Computing details top

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.

Figures top
[Figure 1] Fig. 1. Displacement ellipsoid plot.
[Figure 2] Fig. 2. Packing diagram.
(E)-2,4,6-Triisopropyl-N-[2- (2-pyridylmethyleneamino)cyclohexyl]benzenesulfonamide acetonitrile hemisolvate top
Crystal data top
C27H39N3O2S·0.5C2H3NDx = 1.117 Mg m3
Mr = 488.70Mo Kα radiation, λ = 0.71073 Å
Tetragonal, I41/aCell parameters from 6978 reflections
Hall symbol: -I 4adθ = 2.2–22.8°
a = 21.9895 (17) ŵ = 0.14 mm1
c = 24.035 (3) ÅT = 293 K
V = 11622.0 (18) Å3Block, yellow
Z = 160.30 × 0.28 × 0.20 mm
F(000) = 4216
Data collection top
Bruker SMART 1K CCD area-detector
diffractometer
5766 independent reflections
Radiation source: fine-focus sealed tube3108 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.063
Detector resolution: 10 pixels mm-1θmax = 26.1°, θmin = 1.9°
φ and ω scansh = 1727
Absorption correction: multi-scan
(SADABS; Sheldrick, 2002)
k = 2726
Tmin = 0.769, Tmax = 1.000l = 2929
31641 measured reflections
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)] = 0.062Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.216H-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 parametersΔρmax = 0.28 e Å3
0 restraintsΔρmin = 0.33 e Å3
Crystal data top
C27H39N3O2S·0.5C2H3NZ = 16
Mr = 488.70Mo Kα radiation
Tetragonal, I41/aµ = 0.14 mm1
a = 21.9895 (17) ÅT = 293 K
c = 24.035 (3) Å0.30 × 0.28 × 0.20 mm
V = 11622.0 (18) Å3
Data collection top
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 = 1.000Rint = 0.063
31641 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0620 restraints
wR(F2) = 0.216H-atom parameters constrained
S = 1.04Δρmax = 0.28 e Å3
5766 reflectionsΔρmin = 0.33 e Å3
313 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
S10.12749 (4)0.60119 (4)0.03742 (3)0.0730 (3)
O10.14047 (12)0.57455 (12)0.01578 (8)0.0999 (8)
O20.09863 (11)0.65909 (10)0.03769 (10)0.0917 (7)
C10.07243 (18)0.68154 (17)0.01539 (14)0.0931 (11)
H10.05860.70050.01680.112*
N20.03673 (11)0.60214 (11)0.07332 (10)0.0693 (7)
N30.08473 (11)0.55429 (11)0.06978 (9)0.0688 (6)
H3A0.07980.51860.05590.083*
N40.00000.75000.2299 (5)0.265 (6)
N10.09302 (12)0.59030 (12)0.06422 (11)0.0794 (7)
C40.11168 (15)0.62558 (18)0.10696 (13)0.0843 (9)
H40.12570.60640.13900.101*
C30.11121 (16)0.68721 (18)0.10611 (15)0.0890 (10)
H3B0.12420.70930.13690.107*
C20.09163 (19)0.71601 (18)0.05998 (16)0.1019 (12)
H20.09110.75830.05820.122*
C50.07375 (13)0.61963 (14)0.01864 (12)0.0687 (8)
C60.05335 (13)0.58042 (15)0.02798 (12)0.0715 (8)
H6A0.05300.53850.02320.086*
C70.01480 (13)0.56002 (14)0.11595 (11)0.0676 (8)
H7A0.02330.51810.10460.081*
C80.04702 (16)0.57368 (19)0.17042 (14)0.0940 (11)
H8A0.04180.61630.17950.113*
H8B0.09020.56600.16610.113*
C90.02260 (19)0.5352 (2)0.21751 (14)0.1026 (12)
H9A0.04320.54580.25180.123*
H9B0.03040.49260.20980.123*
C100.0446 (2)0.5451 (2)0.22403 (13)0.1036 (12)
H10A0.06000.51870.25310.124*
H10B0.05200.58690.23530.124*
C110.07834 (16)0.53241 (18)0.17040 (13)0.0898 (10)
H11A0.07520.48940.16180.108*
H11B0.12100.54200.17540.108*
C120.05348 (13)0.56906 (13)0.12206 (11)0.0633 (7)
H12A0.06070.61220.13000.076*
C130.19802 (13)0.60672 (14)0.07480 (11)0.0660 (7)
C140.24248 (16)0.56126 (15)0.06689 (13)0.0758 (8)
C150.23114 (18)0.50094 (16)0.03670 (16)0.0942 (11)
H15A0.18730.49770.02980.113*
C160.2634 (3)0.5001 (2)0.0199 (2)0.160 (2)
H16A0.25030.53430.04160.240*
H16B0.25360.46320.03920.240*
H16C0.30660.50230.01440.240*
C170.2495 (2)0.44733 (19)0.0724 (3)0.145 (2)
H17A0.22790.44880.10700.217*
H17B0.29250.44900.07940.217*
H17C0.23990.41020.05330.217*
C180.29944 (17)0.57050 (17)0.08867 (15)0.0882 (10)
H18A0.32910.54130.08190.106*
C190.31504 (17)0.62005 (19)0.11959 (16)0.0926 (10)
C200.3802 (2)0.6297 (3)0.1408 (3)0.1416 (18)
H20A0.39490.58790.14550.170*
C210.3848 (3)0.6544 (3)0.1970 (2)0.174 (2)
H21A0.42690.65840.20700.261*
H21B0.36490.62760.22270.261*
H21C0.36560.69370.19820.261*
C220.4194 (3)0.6531 (5)0.0965 (3)0.241 (5)
H22A0.45990.65860.11060.362*
H22B0.40400.69140.08360.362*
H22C0.42020.62470.06610.362*
C230.27044 (17)0.66180 (17)0.13025 (14)0.0859 (10)
H23A0.27990.69510.15250.103*
C240.21147 (15)0.65686 (14)0.10948 (12)0.0742 (8)
C250.16786 (18)0.70501 (17)0.13004 (16)0.0975 (11)
H25A0.12720.69270.11780.117*
C260.1808 (2)0.7662 (2)0.1032 (2)0.1426 (18)
H26A0.17880.76230.06340.214*
H26B0.22060.77980.11380.214*
H26C0.15110.79530.11540.214*
C270.1664 (3)0.7066 (3)0.1933 (2)0.168 (2)
H27A0.15670.66680.20730.252*
H27B0.13610.73500.20550.252*
H27C0.20550.71880.20710.252*
C280.00000.75000.1224 (3)0.1063 (17)
C290.00000.75000.1818 (6)0.153 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0865 (6)0.0789 (5)0.0537 (4)0.0073 (4)0.0018 (4)0.0124 (4)
O10.133 (2)0.1216 (19)0.0456 (12)0.0107 (16)0.0040 (12)0.0053 (11)
O20.1019 (16)0.0725 (14)0.1008 (17)0.0140 (12)0.0035 (13)0.0284 (12)
C10.123 (3)0.082 (2)0.074 (2)0.002 (2)0.019 (2)0.0050 (18)
N20.0696 (15)0.0797 (16)0.0586 (14)0.0029 (12)0.0122 (11)0.0093 (12)
N30.0828 (16)0.0666 (14)0.0572 (13)0.0009 (12)0.0009 (12)0.0025 (11)
N40.251 (12)0.356 (16)0.188 (10)0.023 (10)0.0000.000
N10.0896 (18)0.0865 (17)0.0620 (15)0.0000 (14)0.0183 (13)0.0053 (13)
C40.092 (2)0.103 (3)0.0588 (19)0.0096 (19)0.0131 (16)0.0068 (17)
C30.094 (2)0.100 (3)0.073 (2)0.016 (2)0.0032 (19)0.026 (2)
C20.137 (3)0.087 (2)0.082 (2)0.011 (2)0.022 (2)0.010 (2)
C50.0682 (18)0.079 (2)0.0588 (17)0.0029 (15)0.0073 (14)0.0069 (14)
C60.0725 (19)0.0752 (19)0.0668 (19)0.0061 (15)0.0134 (15)0.0092 (15)
C70.0730 (18)0.0712 (18)0.0586 (16)0.0110 (15)0.0134 (14)0.0113 (14)
C80.083 (2)0.122 (3)0.077 (2)0.001 (2)0.0104 (18)0.026 (2)
C90.119 (3)0.124 (3)0.064 (2)0.000 (2)0.014 (2)0.025 (2)
C100.129 (3)0.132 (3)0.0504 (18)0.004 (3)0.0170 (19)0.0176 (19)
C110.090 (2)0.117 (3)0.0625 (19)0.016 (2)0.0151 (17)0.0133 (18)
C120.0727 (18)0.0670 (17)0.0501 (15)0.0021 (14)0.0073 (13)0.0026 (13)
C130.0754 (18)0.0720 (18)0.0506 (15)0.0039 (15)0.0152 (13)0.0044 (13)
C140.082 (2)0.077 (2)0.0688 (18)0.0065 (17)0.0151 (16)0.0061 (15)
C150.097 (2)0.077 (2)0.108 (3)0.0118 (19)0.024 (2)0.012 (2)
C160.190 (5)0.142 (4)0.147 (4)0.025 (4)0.085 (4)0.058 (3)
C170.125 (4)0.076 (3)0.233 (6)0.007 (2)0.018 (4)0.014 (3)
C180.078 (2)0.095 (3)0.091 (2)0.0136 (19)0.0080 (19)0.003 (2)
C190.083 (2)0.105 (3)0.090 (2)0.001 (2)0.0008 (19)0.006 (2)
C200.101 (3)0.174 (5)0.149 (5)0.005 (3)0.021 (3)0.026 (4)
C210.163 (5)0.246 (7)0.114 (4)0.020 (5)0.046 (4)0.013 (5)
C220.096 (4)0.447 (14)0.181 (7)0.063 (6)0.010 (4)0.069 (8)
C230.089 (2)0.094 (2)0.075 (2)0.009 (2)0.0057 (18)0.0062 (18)
C240.082 (2)0.078 (2)0.0624 (18)0.0012 (16)0.0182 (16)0.0027 (15)
C250.092 (2)0.095 (3)0.105 (3)0.000 (2)0.023 (2)0.026 (2)
C260.129 (4)0.089 (3)0.210 (5)0.017 (3)0.030 (4)0.009 (3)
C270.181 (5)0.198 (5)0.125 (4)0.016 (4)0.055 (4)0.066 (4)
C280.115 (4)0.099 (4)0.105 (4)0.019 (3)0.0000.000
C290.139 (7)0.137 (6)0.184 (10)0.001 (5)0.0000.000
Geometric parameters (Å, º) top
S1—O21.423 (2)C13—C241.414 (4)
S1—O11.435 (2)C14—C181.373 (5)
S1—N31.598 (2)C14—C151.532 (5)
S1—C131.796 (3)C15—C171.512 (6)
C1—C51.364 (5)C15—C161.536 (5)
C1—C21.379 (5)C15—H15A0.9800
C1—H10.9300C16—H16A0.9600
N2—C61.245 (4)C16—H16B0.9600
N2—C71.463 (3)C16—H16C0.9600
N3—C121.469 (3)C17—H17A0.9600
N3—H3A0.8600C17—H17B0.9600
N4—C291.157 (12)C17—H17C0.9600
N1—C51.340 (4)C18—C191.363 (5)
N1—C41.351 (4)C18—H18A0.9300
C4—C31.356 (5)C19—C231.367 (5)
C4—H40.9300C19—C201.535 (6)
C3—C21.347 (5)C20—C211.460 (7)
C3—H3B0.9300C20—C221.465 (8)
C2—H20.9300C20—H20A0.9800
C5—C61.483 (4)C21—H21A0.9600
C6—H6A0.9300C21—H21B0.9600
C7—C81.518 (4)C21—H21C0.9600
C7—C121.522 (4)C22—H22A0.9600
C7—H7A0.9800C22—H22B0.9600
C8—C91.512 (5)C22—H22C0.9600
C8—H8A0.9700C23—C241.394 (5)
C8—H8B0.9700C23—H23A0.9300
C9—C101.503 (5)C24—C251.512 (5)
C9—H9A0.9700C25—C261.520 (6)
C9—H9B0.9700C25—C271.522 (6)
C10—C111.513 (5)C25—H25A0.9800
C10—H10A0.9700C26—H26A0.9600
C10—H10B0.9700C26—H26B0.9600
C11—C121.516 (4)C26—H26C0.9600
C11—H11A0.9700C27—H27A0.9600
C11—H11B0.9700C27—H27B0.9600
C12—H12A0.9800C27—H27C0.9600
C13—C141.411 (4)C28—C291.427 (13)
O2—S1—O1117.26 (14)C18—C14—C15117.2 (3)
O2—S1—N3108.23 (14)C13—C14—C15124.4 (3)
O1—S1—N3106.69 (14)C17—C15—C14111.3 (4)
O2—S1—C13108.81 (15)C17—C15—C16111.7 (4)
O1—S1—C13107.55 (14)C14—C15—C16110.8 (3)
N3—S1—C13107.96 (13)C17—C15—H15A107.6
C5—C1—C2119.8 (3)C14—C15—H15A107.6
C5—C1—H1120.1C16—C15—H15A107.6
C2—C1—H1120.1C15—C16—H16A109.5
C6—N2—C7117.8 (3)C15—C16—H16B109.5
C12—N3—S1123.3 (2)H16A—C16—H16B109.5
C12—N3—H3A118.3C15—C16—H16C109.5
S1—N3—H3A118.3H16A—C16—H16C109.5
C5—N1—C4116.2 (3)H16B—C16—H16C109.5
N1—C4—C3124.1 (3)C15—C17—H17A109.5
N1—C4—H4118.0C15—C17—H17B109.5
C3—C4—H4118.0H17A—C17—H17B109.5
C2—C3—C4119.0 (3)C15—C17—H17C109.5
C2—C3—H3B120.5H17A—C17—H17C109.5
C4—C3—H3B120.5H17B—C17—H17C109.5
C3—C2—C1118.6 (4)C19—C18—C14123.8 (3)
C3—C2—H2120.7C19—C18—H18A118.1
C1—C2—H2120.7C14—C18—H18A118.1
N1—C5—C1122.3 (3)C18—C19—C23117.3 (3)
N1—C5—C6115.7 (3)C18—C19—C20121.7 (4)
C1—C5—C6122.0 (3)C23—C19—C20121.0 (4)
N2—C6—C5121.8 (3)C21—C20—C22120.0 (5)
N2—C6—H6A119.1C21—C20—C19115.1 (5)
C5—C6—H6A119.1C22—C20—C19110.9 (5)
N2—C7—C8109.0 (3)C21—C20—H20A102.6
N2—C7—C12108.1 (2)C22—C20—H20A102.6
C8—C7—C12110.6 (2)C19—C20—H20A102.6
N2—C7—H7A109.7C20—C21—H21A109.5
C8—C7—H7A109.7C20—C21—H21B109.5
C12—C7—H7A109.7H21A—C21—H21B109.5
C9—C8—C7111.6 (3)C20—C21—H21C109.5
C9—C8—H8A109.3H21A—C21—H21C109.5
C7—C8—H8A109.3H21B—C21—H21C109.5
C9—C8—H8B109.3C20—C22—H22A109.5
C7—C8—H8B109.3C20—C22—H22B109.5
H8A—C8—H8B108.0H22A—C22—H22B109.5
C10—C9—C8110.2 (3)C20—C22—H22C109.5
C10—C9—H9A109.6H22A—C22—H22C109.5
C8—C9—H9A109.6H22B—C22—H22C109.5
C10—C9—H9B109.6C19—C23—C24123.2 (3)
C8—C9—H9B109.6C19—C23—H23A118.4
H9A—C9—H9B108.1C24—C23—H23A118.4
C9—C10—C11111.5 (3)C23—C24—C13117.8 (3)
C9—C10—H10A109.3C23—C24—C25114.7 (3)
C11—C10—H10A109.3C13—C24—C25127.3 (3)
C9—C10—H10B109.3C24—C25—C26111.3 (3)
C11—C10—H10B109.3C24—C25—C27110.8 (4)
H10A—C10—H10B108.0C26—C25—C27114.1 (4)
C10—C11—C12112.2 (3)C24—C25—H25A106.7
C10—C11—H11A109.2C26—C25—H25A106.7
C12—C11—H11A109.2C27—C25—H25A106.7
C10—C11—H11B109.2C25—C26—H26A109.5
C12—C11—H11B109.2C25—C26—H26B109.5
H11A—C11—H11B107.9H26A—C26—H26B109.5
N3—C12—C11111.7 (2)C25—C26—H26C109.5
N3—C12—C7110.5 (2)H26A—C26—H26C109.5
C11—C12—C7111.1 (2)H26B—C26—H26C109.5
N3—C12—H12A107.8C25—C27—H27A109.5
C11—C12—H12A107.8C25—C27—H27B109.5
C7—C12—H12A107.8H27A—C27—H27B109.5
C14—C13—C24119.1 (3)C25—C27—H27C109.5
C14—C13—S1118.9 (2)H27A—C27—H27C109.5
C24—C13—S1121.9 (2)H27B—C27—H27C109.5
C18—C14—C13118.4 (3)N4—C29—C28180.000 (3)
O2—S1—N3—C1242.8 (3)O2—S1—C13—C2414.6 (3)
O1—S1—N3—C12169.8 (2)O1—S1—C13—C24142.6 (2)
C13—S1—N3—C1274.8 (2)N3—S1—C13—C24102.6 (2)
C5—N1—C4—C30.7 (5)C24—C13—C14—C186.5 (4)
N1—C4—C3—C20.7 (6)S1—C13—C14—C18170.1 (2)
C4—C3—C2—C10.4 (6)C24—C13—C14—C15171.8 (3)
C5—C1—C2—C30.2 (6)S1—C13—C14—C1511.6 (4)
C4—N1—C5—C10.5 (5)C18—C14—C15—C1752.0 (4)
C4—N1—C5—C6180.0 (3)C13—C14—C15—C17126.4 (4)
C2—C1—C5—N10.3 (6)C18—C14—C15—C1672.9 (5)
C2—C1—C5—C6179.7 (3)C13—C14—C15—C16108.7 (4)
C7—N2—C6—C5177.3 (3)C13—C14—C18—C192.8 (5)
N1—C5—C6—N2177.1 (3)C15—C14—C18—C19175.6 (3)
C1—C5—C6—N23.5 (5)C14—C18—C19—C231.6 (6)
C6—N2—C7—C8130.4 (3)C14—C18—C19—C20177.2 (4)
C6—N2—C7—C12109.4 (3)C18—C19—C20—C21140.9 (5)
N2—C7—C8—C9175.2 (3)C23—C19—C20—C2140.4 (7)
C12—C7—C8—C956.6 (4)C18—C19—C20—C2278.8 (7)
C7—C8—C9—C1057.6 (4)C23—C19—C20—C22100.0 (6)
C8—C9—C10—C1156.1 (5)C18—C19—C23—C242.4 (5)
C9—C10—C11—C1254.9 (5)C20—C19—C23—C24176.5 (4)
S1—N3—C12—C11112.8 (3)C19—C23—C24—C131.4 (5)
S1—N3—C12—C7122.9 (2)C19—C23—C24—C25175.2 (3)
C10—C11—C12—N3177.4 (3)C14—C13—C24—C235.8 (4)
C10—C11—C12—C753.5 (4)S1—C13—C24—C23170.7 (2)
N2—C7—C12—N362.3 (3)C14—C13—C24—C25170.3 (3)
C8—C7—C12—N3178.5 (3)S1—C13—C24—C2513.2 (4)
N2—C7—C12—C11173.1 (2)C23—C24—C25—C2673.3 (4)
C8—C7—C12—C1154.0 (3)C13—C24—C25—C26110.5 (4)
O2—S1—C13—C14161.9 (2)C23—C24—C25—C2754.8 (5)
O1—S1—C13—C1434.0 (3)C13—C24—C25—C27121.4 (4)
N3—S1—C13—C1480.8 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H3A···N1i0.862.423.188 (4)149
Symmetry code: (i) x, y+1, z.

Experimental details

Crystal data
Chemical formulaC27H39N3O2S·0.5C2H3N
Mr488.70
Crystal system, space groupTetragonal, I41/a
Temperature (K)293
a, c (Å)21.9895 (17), 24.035 (3)
V3)11622.0 (18)
Z16
Radiation typeMo Kα
µ (mm1)0.14
Crystal size (mm)0.30 × 0.28 × 0.20
Data collection
DiffractometerBruker SMART 1K CCD area-detector
Absorption correctionMulti-scan
(SADABS; Sheldrick, 2002)
Tmin, Tmax0.769, 1.000
No. of measured, independent and
observed [I > 2σ(I)] reflections
31641, 5766, 3108
Rint0.063
(sin θ/λ)max1)0.619
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.062, 0.216, 1.04
No. of reflections5766
No. of parameters313
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.28, 0.33

Computer programs: SMART (Bruker, 1999), SAINT (Bruker, 1999), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Sheldrick, 2000), SHELXTL.

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H3A···N1i0.862.423.188 (4)148.8
Symmetry code: (i) x, y+1, z.
 

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