# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 _journal_year ? _journal_volume ? _journal_page_first ? _publ_author_name 'Hasim Ibrahim' data_has30 _database_code_depnum_ccdc_archive 'CCDC 895104' #TrackingRef '- has30_CIF_CC-COM-08-2012-035596.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H21 N O2' _chemical_formula_sum 'C16 H21 N O2' _chemical_formula_weight 259.34 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 16.6351(1) _cell_length_b 4.84961(3) _cell_length_c 17.4700(1) _cell_angle_alpha 90.00 _cell_angle_beta 101.3548(6) _cell_angle_gamma 90.00 _cell_volume 1381.784(14) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 22796 _cell_measurement_theta_min 3.3510 _cell_measurement_theta_max 76.8072 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.2805 _exptl_crystal_size_mid 0.2650 _exptl_crystal_size_min 0.1970 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.247 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 560 _exptl_absorpt_coefficient_mu 0.646 _exptl_absorpt_correction_type analytical _exptl_absorpt_correction_T_min 0.872 _exptl_absorpt_correction_T_max 0.925 _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.36 (release 02-08-2010 CrysAlis171 .NET) (compiled Aug 2 2010,13:00:58) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. Reid. (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) ; _exptl_special_details ; All hydrogen atoms were located in the difference fourier map and allowed to refine freely. The O-H bond length is 0.88(2) \%A, the N-H bond length is 0.86(2) \%A and C-H bond lengths range from 0.97(2) \%A to 1.02(2) \%A. ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'SuperNova (Cu) X-ray Source' _diffrn_radiation_monochromator mirror _diffrn_measurement_device_type 'SuperNova, Dual, Cu at zero, Atlas' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 10.3196 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 27284 _diffrn_reflns_av_R_equivalents 0.0173 _diffrn_reflns_av_sigmaI/netI 0.0081 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 3.35 _diffrn_reflns_theta_max 77.01 _reflns_number_total 2897 _reflns_number_gt 2858 _reflns_threshold_expression I>2\s(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.36 (release 02-08-2010 CrysAlis171 .NET) (compiled Aug 2 2010,13:00:58) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.36 (release 02-08-2010 CrysAlis171 .NET) (compiled Aug 2 2010,13:00:58) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.36 (release 02-08-2010 CrysAlis171 .NET) (compiled Aug 2 2010,13:00:58) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0362P)^2^+0.5572P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0041(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2897 _refine_ls_number_parameters 257 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0323 _refine_ls_R_factor_gt 0.0320 _refine_ls_wR_factor_ref 0.0793 _refine_ls_wR_factor_gt 0.0791 _refine_ls_goodness_of_fit_ref 1.019 _refine_ls_restrained_S_all 1.019 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.27338(5) 0.84016(19) 0.36611(5) 0.01527(19) Uani 1 1 d . . . H1 H 0.2729(7) 1.024(3) 0.3926(7) 0.017(3) Uiso 1 1 d . . . O1 O 0.24836(4) 0.90021(14) 0.28437(4) 0.01782(16) Uani 1 1 d . . . H1O1 H 0.2439(9) 0.741(3) 0.2600(9) 0.043(4) Uiso 1 1 d . . . C2 C 0.20746(6) 0.6508(2) 0.38706(5) 0.0198(2) Uani 1 1 d . . . H2A H 0.1554(8) 0.757(3) 0.3740(7) 0.027(3) Uiso 1 1 d . . . H2B H 0.2020(7) 0.488(3) 0.3514(7) 0.025(3) Uiso 1 1 d . . . C3 C 0.22034(6) 0.5458(2) 0.47133(6) 0.0239(2) Uani 1 1 d . . . H3A H 0.2641(8) 0.403(3) 0.4808(7) 0.026(3) Uiso 1 1 d . . . H3B H 0.1683(9) 0.446(3) 0.4775(8) 0.036(4) Uiso 1 1 d . . . C4 C 0.24176(7) 0.7720(2) 0.53039(6) 0.0267(2) Uani 1 1 d . . . H4 H 0.1963(9) 0.876(3) 0.5442(8) 0.038(4) Uiso 1 1 d . . . C5 C 0.31853(8) 0.8423(2) 0.56002(6) 0.0290(2) Uani 1 1 d . . . H5 H 0.3287(9) 0.996(3) 0.5958(9) 0.043(4) Uiso 1 1 d . . . C6 C 0.39269(7) 0.7045(2) 0.53951(6) 0.0288(2) Uani 1 1 d . . . H6A H 0.3847(7) 0.501(3) 0.5344(7) 0.025(3) Uiso 1 1 d . . . H6B H 0.4400(9) 0.736(3) 0.5826(9) 0.042(4) Uiso 1 1 d . . . C7 C 0.41473(6) 0.8125(2) 0.46361(6) 0.0237(2) Uani 1 1 d . . . H7A H 0.4154(8) 1.021(3) 0.4660(7) 0.029(3) Uiso 1 1 d . . . H7B H 0.4722(8) 0.748(3) 0.4622(7) 0.029(3) Uiso 1 1 d . . . C8 C 0.36219(5) 0.72714(18) 0.38416(5) 0.01605(19) Uani 1 1 d . . . H8 H 0.3620(7) 0.524(3) 0.3784(7) 0.019(3) Uiso 1 1 d . . . C9 C 0.40760(5) 0.85023(19) 0.32415(5) 0.01731(19) Uani 1 1 d . . . O2 O 0.41864(4) 1.10196(14) 0.32110(4) 0.02332(17) Uani 1 1 d . . . N N 0.43681(5) 0.67202(17) 0.27793(5) 0.01984(18) Uani 1 1 d . . . H1N H 0.4266(8) 0.498(3) 0.2815(7) 0.027(3) Uiso 1 1 d . . . C10 C 0.47875(7) 0.7690(2) 0.21699(7) 0.0282(2) Uani 1 1 d . . . H10A H 0.5098(9) 0.932(3) 0.2382(8) 0.037(4) Uiso 1 1 d . . . H10B H 0.4373(9) 0.824(3) 0.1690(9) 0.040(4) Uiso 1 1 d . . . C11 C 0.53567(6) 0.5542(2) 0.19541(6) 0.0204(2) Uani 1 1 d . . . C12 C 0.52024(6) 0.4359(2) 0.12146(6) 0.0244(2) Uani 1 1 d . . . H12 H 0.4714(8) 0.492(3) 0.0837(8) 0.032(3) Uiso 1 1 d . . . C13 C 0.57331(7) 0.2405(2) 0.10092(6) 0.0273(2) Uani 1 1 d . . . H13 H 0.5604(8) 0.157(3) 0.0484(8) 0.038(4) Uiso 1 1 d . . . C14 C 0.64270(7) 0.1625(2) 0.15402(6) 0.0268(2) Uani 1 1 d . . . H14 H 0.6795(8) 0.025(3) 0.1403(8) 0.037(4) Uiso 1 1 d . . . C15 C 0.65865(6) 0.2785(2) 0.22791(6) 0.0253(2) Uani 1 1 d . . . H15 H 0.7071(8) 0.222(3) 0.2666(8) 0.036(4) Uiso 1 1 d . . . C16 C 0.60553(6) 0.4728(2) 0.24848(6) 0.0226(2) Uani 1 1 d . . . H16 H 0.6167(8) 0.554(3) 0.3006(8) 0.032(3) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0178(4) 0.0151(4) 0.0135(4) -0.0001(3) 0.0045(3) 0.0013(3) O1 0.0233(3) 0.0153(3) 0.0145(3) 0.0006(3) 0.0027(2) 0.0001(3) C2 0.0173(4) 0.0221(5) 0.0212(5) 0.0009(4) 0.0067(3) -0.0005(4) C3 0.0280(5) 0.0233(5) 0.0231(5) 0.0028(4) 0.0115(4) -0.0027(4) C4 0.0404(6) 0.0233(5) 0.0209(5) 0.0031(4) 0.0171(4) 0.0045(4) C5 0.0510(7) 0.0224(5) 0.0150(4) -0.0007(4) 0.0095(4) -0.0031(5) C6 0.0323(5) 0.0314(6) 0.0199(5) 0.0037(4) -0.0018(4) -0.0021(4) C7 0.0213(5) 0.0253(5) 0.0228(5) 0.0014(4) 0.0001(4) -0.0022(4) C8 0.0166(4) 0.0138(4) 0.0185(4) 0.0010(3) 0.0054(3) 0.0007(3) C9 0.0149(4) 0.0144(4) 0.0232(4) 0.0019(3) 0.0051(3) 0.0006(3) O2 0.0264(4) 0.0128(3) 0.0336(4) 0.0015(3) 0.0130(3) -0.0010(3) N 0.0220(4) 0.0130(4) 0.0283(4) 0.0032(3) 0.0144(3) 0.0008(3) C10 0.0321(5) 0.0217(5) 0.0374(6) 0.0099(4) 0.0233(5) 0.0077(4) C11 0.0210(4) 0.0174(4) 0.0265(5) 0.0055(4) 0.0135(4) 0.0010(4) C12 0.0208(5) 0.0291(5) 0.0245(5) 0.0061(4) 0.0073(4) -0.0014(4) C13 0.0328(5) 0.0295(5) 0.0228(5) -0.0033(4) 0.0132(4) -0.0043(4) C14 0.0287(5) 0.0235(5) 0.0335(5) 0.0006(4) 0.0188(4) 0.0045(4) C15 0.0205(5) 0.0271(5) 0.0295(5) 0.0045(4) 0.0079(4) 0.0034(4) C16 0.0259(5) 0.0218(5) 0.0218(5) -0.0007(4) 0.0085(4) -0.0003(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O1 1.4364(10) . ? C1 C2 1.5289(12) . ? C1 C8 1.5488(12) . ? C1 H1 1.004(12) . ? O1 H1O1 0.878(17) . ? C2 C3 1.5326(13) . ? C2 H2A 0.994(13) . ? C2 H2B 1.001(13) . ? C3 C4 1.5004(15) . ? C3 H3A 0.995(13) . ? C3 H3B 1.016(14) . ? C4 C5 1.3246(17) . ? C4 H4 0.978(15) . ? C5 C6 1.5072(17) . ? C5 H5 0.967(16) . ? C6 C7 1.5358(14) . ? C6 H6A 0.999(13) . ? C6 H6B 0.988(15) . ? C7 C8 1.5440(13) . ? C7 H7A 1.013(14) . ? C7 H7B 1.010(13) . ? C8 C9 1.5291(12) . ? C8 H8 0.988(13) . ? C9 O2 1.2372(12) . ? C9 N 1.3377(12) . ? N C10 1.4608(12) . ? N H1N 0.864(15) . ? C10 C11 1.5045(13) . ? C10 H10A 0.978(15) . ? C10 H10B 1.010(15) . ? C11 C12 1.3907(14) . ? C11 C16 1.3934(14) . ? C12 C13 1.3896(15) . ? C12 H12 0.979(14) . ? C13 C14 1.3836(16) . ? C13 H13 0.987(14) . ? C14 C15 1.3852(15) . ? C14 H14 0.967(15) . ? C15 C16 1.3866(14) . ? C15 H15 0.984(14) . ? C16 H16 0.976(14) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 C1 C2 106.18(7) . . ? O1 C1 C8 110.63(7) . . ? C2 C1 C8 116.04(7) . . ? O1 C1 H1 104.5(6) . . ? C2 C1 H1 110.6(6) . . ? C8 C1 H1 108.3(6) . . ? C1 O1 H1O1 106.5(10) . . ? C1 C2 C3 117.29(8) . . ? C1 C2 H2A 105.6(7) . . ? C3 C2 H2A 110.0(7) . . ? C1 C2 H2B 107.9(7) . . ? C3 C2 H2B 108.3(7) . . ? H2A C2 H2B 107.3(10) . . ? C4 C3 C2 112.76(8) . . ? C4 C3 H3A 109.1(7) . . ? C2 C3 H3A 110.5(7) . . ? C4 C3 H3B 111.6(8) . . ? C2 C3 H3B 107.4(8) . . ? H3A C3 H3B 105.2(11) . . ? C5 C4 C3 122.48(10) . . ? C5 C4 H4 120.2(8) . . ? C3 C4 H4 117.2(8) . . ? C4 C5 C6 124.36(10) . . ? C4 C5 H5 118.9(9) . . ? C6 C5 H5 116.7(9) . . ? C5 C6 C7 113.55(9) . . ? C5 C6 H6A 111.1(7) . . ? C7 C6 H6A 108.1(7) . . ? C5 C6 H6B 108.5(9) . . ? C7 C6 H6B 108.3(9) . . ? H6A C6 H6B 107.0(11) . . ? C6 C7 C8 119.70(8) . . ? C6 C7 H7A 108.0(7) . . ? C8 C7 H7A 107.7(7) . . ? C6 C7 H7B 107.7(7) . . ? C8 C7 H7B 105.4(7) . . ? H7A C7 H7B 107.9(10) . . ? C9 C8 C7 104.06(7) . . ? C9 C8 C1 107.60(7) . . ? C7 C8 C1 115.88(8) . . ? C9 C8 H8 108.2(7) . . ? C7 C8 H8 110.4(7) . . ? C1 C8 H8 110.3(7) . . ? O2 C9 N 122.47(9) . . ? O2 C9 C8 120.82(8) . . ? N C9 C8 116.67(8) . . ? C9 N C10 120.95(8) . . ? C9 N H1N 119.1(9) . . ? C10 N H1N 119.7(9) . . ? N C10 C11 111.98(8) . . ? N C10 H10A 106.1(8) . . ? C11 C10 H10A 110.2(8) . . ? N C10 H10B 110.0(8) . . ? C11 C10 H10B 109.5(8) . . ? H10A C10 H10B 109.0(12) . . ? C12 C11 C16 118.58(9) . . ? C12 C11 C10 120.55(9) . . ? C16 C11 C10 120.87(9) . . ? C13 C12 C11 120.73(9) . . ? C13 C12 H12 120.1(8) . . ? C11 C12 H12 119.2(8) . . ? C14 C13 C12 120.12(10) . . ? C14 C13 H13 120.7(8) . . ? C12 C13 H13 119.2(8) . . ? C13 C14 C15 119.68(10) . . ? C13 C14 H14 120.5(8) . . ? C15 C14 H14 119.8(8) . . ? C14 C15 C16 120.19(10) . . ? C14 C15 H15 120.5(8) . . ? C16 C15 H15 119.3(8) . . ? C15 C16 C11 120.71(9) . . ? C15 C16 H16 120.1(8) . . ? C11 C16 H16 119.2(8) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 C1 C2 C3 178.03(8) . . . . ? C8 C1 C2 C3 54.66(11) . . . . ? C1 C2 C3 C4 49.12(12) . . . . ? C2 C3 C4 C5 -91.75(12) . . . . ? C3 C4 C5 C6 -0.86(16) . . . . ? C4 C5 C6 C7 82.45(13) . . . . ? C5 C6 C7 C8 -74.69(13) . . . . ? C6 C7 C8 C9 -174.66(9) . . . . ? C6 C7 C8 C1 67.44(12) . . . . ? O1 C1 C8 C9 28.80(10) . . . . ? C2 C1 C8 C9 149.81(8) . . . . ? O1 C1 C8 C7 144.73(8) . . . . ? C2 C1 C8 C7 -94.26(10) . . . . ? C7 C8 C9 O2 -60.28(11) . . . . ? C1 C8 C9 O2 63.20(11) . . . . ? C7 C8 C9 N 117.35(9) . . . . ? C1 C8 C9 N -119.17(9) . . . . ? O2 C9 N C10 -4.43(15) . . . . ? C8 C9 N C10 177.98(9) . . . . ? C9 N C10 C11 156.12(9) . . . . ? N C10 C11 C12 114.14(11) . . . . ? N C10 C11 C16 -66.88(13) . . . . ? C16 C11 C12 C13 0.03(15) . . . . ? C10 C11 C12 C13 179.03(9) . . . . ? C11 C12 C13 C14 -0.36(16) . . . . ? C12 C13 C14 C15 0.48(16) . . . . ? C13 C14 C15 C16 -0.26(16) . . . . ? C14 C15 C16 C11 -0.07(15) . . . . ? C12 C11 C16 C15 0.19(14) . . . . ? C10 C11 C16 C15 -178.81(9) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N H1N O2 0.864(15) 2.056(15) 2.8970(11) 164.2(12) 1_545 O1 H1O1 O1 0.878(17) 1.840(17) 2.7111(6) 171.0(15) 2_545 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 77.01 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.300 _refine_diff_density_min -0.164 _refine_diff_density_rms 0.032