Supporting Information Regioselective base-mediated cyclizations of mono-n-acylpropargylguanadines. Justin M. Salvant, Anne V. Edwards, Daniel Z. Kurek and Ryan E. Looper* * Department of Chemistry, University of Utah, 315 South 1400 East, Salt Lake City, UT, 84112 r.looper@utah.edu 1. Crystal Structure Report for 4m p.2 2. Representative 1 H and 13 C NMR Spectra p.5 S1
Crystal Structure Report for 4m (ellipsoids are shown at a 35% probability level) A colorless prism-like specimen of C 26 H 25 N 3 O 3, approximate dimensions 0.168 mm x 0.336 mm x 0.350 mm, was used for the X-ray crystallographic analysis. The X-ray intensity data were measured.ref9 WinGX A Windows Program for Crystal Structure Analysis. L. J. Farrugia, J. Appl. Crystallogr. 2012, 45, 849-854. Table S1: Data collection details for rl022. Axis dx/m m 2θ/ ω/ φ/ χ/ Width/ Frames Time/s Wavelength/ Å Volt age/ kv Current/ ma Tempe rature/ K Phi 34.403 15.76 25.46 0.00-23.00 1.00 360 9.00 0.71073 50 30.0 150 Omega 34.403-49.18-43.86-170.50-59.92 1.00 96 9.00 0.71073 50 30.0 150 Omega 34.403-42.23-36.84 20.09-55.93 1.00 92 9.00 0.71073 50 30.0 150 Omega 34.403 15.76-337.90-180.00-54.74 1.00 91 9.00 0.71073 50 30.0 150 Omega 34.403-43.08-37.20-81.11-46.23 1.00 87 9.00 0.71073 50 30.0 150 Omega 34.403-46.57-39.21 97.14-33.96 1.00 80 9.00 0.71073 50 30.0 150 Omega 34.403 15.76-337.90-60.00-54.74 1.00 91 9.00 0.71073 50 30.0 150 Omega 34.403 15.76-337.90 60.00-54.74 1.00 91 9.00 0.71073 50 30.0 150 Omega 34.403 0.76-353.90 90.00-54.74 1.00 93 9.00 0.71073 50 30.0 150 Omega 34.403 0.76-353.90 270.00-54.74 1.00 93 9.00 0.71073 50 30.0 150 Phi 34.403 15.76 20.83 0.00-56.56 1.00 360 9.00 0.71073 50 30.0 150 Omega 34.403-49.94-44.95-120.63-65.42 1.00 93 9.00 0.71073 50 30.0 150 S2
Axis dx/m m 2θ/ ω/ φ/ χ/ Width/ Frames Time/s Wavelength/ Å Volt age/ kv Current/ ma Tempe rature/ K Omega 34.403-51.80-46.70 71.81-62.48 1.00 98 9.00 0.71073 50 30.0 150 A total of 1725 frames were collected. The total exposure time was 4.31 hours. The frames were integrated with the Bruker SAINT software package using a narrow-frame algorithm. The integration of the data using a triclinic unit cell yielded a total of 46802 reflections to a maximum θ angle of 27.87 (0.76 Å resolution), of which 5411 were independent (average redundancy 8.649, completeness = 100.0%, Rint = 2.64%, Rsig = 1.47%) and 4636 (85.68%) were greater than 2σ(F2). The final cell constants of a = 10.7534(5) Å, b = 10.9377(5) Å, c = 10.9416(5) Å, α = 89.154(3), β = 62.158(2), γ = 85.360(2), volume = 1133.83(9) Å3, are based upon the refinement of the XYZ-centroids of 9409 reflections above 20 σ(i) with 4.392 < 2θ < 55.82. Data were corrected for absorption effects using the multi-scan method (SADABS). The ratio of minimum to maximum apparent transmission was 0.968. The calculated minimum and maximum transmission coefficients (based on crystal size) are 0.9720 and 0.9860. The structure was solved and refined using the Bruker SHELXTL Software Package, using the space group P -1, with Z = 2 for the formula unit, C26H25N3O3. The final anisotropic fullmatrix least-squares refinement on F2 with 295 variables converged at R1 = 3.75%, for the observed data and wr2 = 9.77% for all data. The goodness-of-fit was 1.028. The largest peak in the final difference electron density synthesis was 0.253 e-/å3 and the largest hole was -0.225 e- /Å3 with an RMS deviation of 0.037 e-/å3. On the basis of the final model, the calculated density was 1.252 g/cm3 and F(000), 452 e-. Table S2. Sample and crystal data for 4m. Identification code rl022 Chemical formula C 26 H 25 N 3 O 3 Formula weight 427.49 g/mol Temperature 150(1) K Wavelength 0.71073 Å Crystal size 0.168 x 0.336 x 0.350 mm Crystal habit colorless prism Crystal system triclinic Space group P -1 Unit cell dimensions a = 10.7534(5) Å α = 89.154(3) b = 10.9377(5) Å β = 62.158(2) c = 10.9416(5) Å γ = 85.360(2) Volume 1133.83(9) Å 3 Z 2 Density (calculated) 1.252 g/cm 3 S3
Absorption coefficient 0.083 mm -1 F(000) 452 Table S3. Data collection and structure refinement for 4m. Theta range for data collection 2.11 to 27.87 Index ranges -14<=h<=14, -14<=k<=14, - 14<=l<=14 Reflections collected 46802 Independent reflections 5411 [R(int) = 0.0264] Coverage of independent reflections 100.0% Absorption correction multi-scan Max. and min. transmission 0.9860 and 0.9720 Structure solution technique direct methods Structure solution program SHELXT-2014/9 (Sheldrick, 2014) Refinement method Full-matrix least-squares on F 2 Refinement program SHELXL-2014/6 (Sheldrick, 2014) Function minimized Σ w(f 2 o - F 2 c ) 2 Data / restraints / parameters 5411 / 0 / 295 Goodness-of-fit on F 2 1.028 Final R indices 4636 data; R1 = 0.0375, wr2 = I>2σ(I) 0.0913 all data R1 = 0.0453, wr2 = 0.0977 Weighting scheme w=1/[σ 2 (F 2 o )+(0.0430P) 2 +0.3887P] where P=(F 2 o +2F 2 c )/3 Largest diff. peak and hole 0.253 and -0.225 eå -3 R.M.S. deviation from mean 0.037 eå -3 S4
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