# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2012 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_4f _database_code_depnum_ccdc_archive 'CCDC 896882' _audit_creation_date 2012-07-20 _audit_creation_method ; Olex2 1.2-alpha (compiled 2012.07.17 svn.r2416, GUI svn.r4280) ; _chemical_name_common ? _chemical_name_systematic ; 3-(benzylamino)-2-methyl-1-phenylpropan-1-ol ; _chemical_formula_moiety 'C17 H21 N O' _chemical_formula_sum 'C17 H21 N O' _chemical_formula_weight 255.35 _chemical_melting_point ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 '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 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_H-M_alt 'P 1 21/c 1' _space_group_name_Hall '-P 2ybc' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, y+1/2, -z+1/2' 3 '-x, -y, -z' 4 'x, -y-1/2, z-1/2' _cell_length_a 13.1529(9) _cell_length_b 13.0660(7) _cell_length_c 9.0291(6) _cell_angle_alpha 90.00 _cell_angle_beta 108.679(8) _cell_angle_gamma 90.00 _cell_volume 1469.97(16) _cell_formula_units_Z 4 _cell_measurement_reflns_used 1726 _cell_measurement_temperature 120 _cell_measurement_theta_max 29.99 _cell_measurement_theta_min 2.84 _exptl_absorpt_coefficient_mu 0.071 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_correction_T_min 0.7874 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.35.10 (2011). Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.154 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description ? _exptl_crystal_F_000 552 _exptl_crystal_size_max 0.56 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.03 _exptl_special_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -78.20 1.00 0.3000 30.0000 omega____ theta____ kappa____ phi______ frames - -20.3107 -57.0000 60.0000 264 #__ type_ start__ end____ width___ exp.time_ 2 omega 62.00 92.00 0.3000 30.0000 omega____ theta____ kappa____ phi______ frames - 20.9357 -154.0000 103.0000 100 #__ type_ start__ end____ width___ exp.time_ 3 omega -19.00 41.00 0.3000 30.0000 omega____ theta____ kappa____ phi______ frames - 20.9357 -57.0000 -90.0000 200 #__ type_ start__ end____ width___ exp.time_ 4 omega -6.00 22.20 0.3000 30.0000 omega____ theta____ kappa____ phi______ frames - 20.9357 77.0000 -150.0000 94 #__ type_ start__ end____ width___ exp.time_ 5 omega 60.00 88.80 0.3000 30.0000 omega____ theta____ kappa____ phi______ frames - 20.9357 77.0000 -150.0000 96 #__ type_ start__ end____ width___ exp.time_ 6 omega 14.00 46.10 0.3000 30.0000 omega____ theta____ kappa____ phi______ frames - 20.9357 19.0000 -150.0000 107 #__ type_ start__ end____ width___ exp.time_ 7 omega -96.00 -34.80 0.3000 30.0000 omega____ theta____ kappa____ phi______ frames - -20.3107 -179.0000 -60.0000 204 #__ type_ start__ end____ width___ exp.time_ 8 omega -90.00 -22.50 0.3000 30.0000 omega____ theta____ kappa____ phi______ frames - -20.3107 -77.0000 -90.0000 225 ; loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 0 0 1 0.0150 0 0 -1 0.0150 -2 0 1 0.3019 2 0 -1 0.2581 0 4 1 0.0856 0 -4 -1 0.0856 1 4 -2 0.0960 _diffrn_reflns_av_R_equivalents 0.0564 _diffrn_reflns_av_unetI/netI 0.0570 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_number 9045 _diffrn_reflns_theta_full 24.99 _diffrn_reflns_theta_max 24.99 _diffrn_reflns_theta_min 2.85 _diffrn_ambient_temperature 120 _diffrn_detector_area_resol_mean 16.15 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_device 'Agilent Technologies, Gemini S Ultra kappa-diffractometer' _diffrn_measurement_device_type 'Sapphire3 CCD area detector' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 0.0228806000 _diffrn_orient_matrix_UB_12 -0.0294085000 _diffrn_orient_matrix_UB_13 0.0686982000 _diffrn_orient_matrix_UB_21 -0.0083858000 _diffrn_orient_matrix_UB_22 -0.0453070000 _diffrn_orient_matrix_UB_23 -0.0456250000 _diffrn_orient_matrix_UB_31 0.0514198000 _diffrn_orient_matrix_UB_32 0.0056872000 _diffrn_orient_matrix_UB_33 -0.0085959000 _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.7107 _diffrn_source 'Enhance (Mo) X-ray Source' _diffrn_standards_number 0 _reflns_number_gt 1988 _reflns_number_total 2586 _reflns_odcompleteness_completeness 99.86 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 27.50 _reflns_threshold_expression I>2\s(I) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.35.10 (2011) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.35.10 (2011) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.35.10 (2011) ; _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement 'XL, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122' _computing_structure_solution 'XS, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122' _refine_diff_density_max 0.257 _refine_diff_density_min -0.199 _refine_diff_density_rms 0.051 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.107 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 181 _refine_ls_number_reflns 2586 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0837 _refine_ls_R_factor_gt 0.0652 _refine_ls_restrained_S_all 1.107 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0464P)^2^+1.2242P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1485 _refine_ls_wR_factor_ref 0.1569 _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. Amino H(1) and hydroxylic H(0) - refall, other H atoms - constr (riding model). ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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 O O 0.03433(14) 0.15162(14) 0.4050(2) 0.0251(5) Uani 1 1 d . . . H0 H 0.057(3) 0.119(3) 0.501(5) 0.080(13) Uiso 1 1 d . . . N N 0.11606(18) 0.46482(16) 0.1735(2) 0.0228(5) Uani 1 1 d . . . H1 H 0.065(2) 0.500(2) 0.193(3) 0.038(9) Uiso 1 1 d . . . C1 C 0.2155(2) 0.17175(18) 0.3952(3) 0.0204(6) Uani 1 1 d . . . C2 C 0.2031(2) 0.0991(2) 0.2778(3) 0.0263(6) Uani 1 1 d . . . H2 H 0.1346 0.0840 0.2111 0.032 Uiso 1 1 d R . . C3 C 0.2902(2) 0.0492(2) 0.2584(3) 0.0352(7) Uani 1 1 d . . . H3 H 0.2803 0.0011 0.1792 0.042 Uiso 1 1 d R . . C4 C 0.3922(3) 0.0706(2) 0.3569(4) 0.0401(8) Uani 1 1 d . . . H4 H 0.4513 0.0370 0.3445 0.048 Uiso 1 1 d R . . C5 C 0.4060(2) 0.1427(2) 0.4747(4) 0.0369(7) Uani 1 1 d . . . H5 H 0.4746 0.1575 0.5413 0.044 Uiso 1 1 d R . . C6 C 0.3180(2) 0.1927(2) 0.4933(3) 0.0272(6) Uani 1 1 d . . . H6 H 0.3279 0.2409 0.5725 0.033 Uiso 1 1 d R . . C7 C 0.11796(19) 0.22474(19) 0.4161(3) 0.0206(6) Uani 1 1 d . . . H7 H 0.1391 0.2553 0.5207 0.025 Uiso 1 1 d R . . C8 C 0.0708(2) 0.30880(19) 0.2961(3) 0.0207(6) Uani 1 1 d . . . H8 H 0.0436 0.2769 0.1926 0.025 Uiso 1 1 d R . . C9 C 0.1574(2) 0.38571(18) 0.2932(3) 0.0213(6) Uani 1 1 d . . . H9A H 0.1853 0.4181 0.3949 0.026 Uiso 1 1 d R . . H9B H 0.2161 0.3499 0.2728 0.026 Uiso 1 1 d R . . C10 C 0.1994(2) 0.5346(2) 0.1578(3) 0.0266(6) Uani 1 1 d . . . H10A H 0.1656 0.5855 0.0793 0.032 Uiso 1 1 d R . . H10B H 0.2487 0.4959 0.1193 0.032 Uiso 1 1 d R . . C11 C 0.2637(2) 0.58956(19) 0.3055(3) 0.0237(6) Uani 1 1 d . . . C12 C 0.3741(2) 0.5821(2) 0.3618(4) 0.0350(7) Uani 1 1 d . . . H12 H 0.4095 0.5419 0.3088 0.042 Uiso 1 1 d R . . C13 C 0.4330(2) 0.6336(2) 0.4958(4) 0.0444(8) Uani 1 1 d . . . H13 H 0.5074 0.6277 0.5321 0.053 Uiso 1 1 d R . . C14 C 0.3816(3) 0.6937(2) 0.5759(4) 0.0398(8) Uani 1 1 d . . . H14 H 0.4211 0.7289 0.6653 0.048 Uiso 1 1 d R . . C15 C 0.2711(2) 0.7009(2) 0.5220(3) 0.0325(7) Uani 1 1 d . . . H15 H 0.2359 0.7405 0.5761 0.039 Uiso 1 1 d R . . C16 C 0.2128(2) 0.6498(2) 0.3885(3) 0.0269(6) Uani 1 1 d . . . H16 H 0.1384 0.6555 0.3530 0.032 Uiso 1 1 d R . . C17 C -0.0230(2) 0.3615(2) 0.3301(3) 0.0281(6) Uani 1 1 d . . . H17A H -0.0744 0.3098 0.3403 0.042 Uiso 1 1 calc R . . H17B H -0.0587 0.4082 0.2442 0.042 Uiso 1 1 calc R . . H17C H 0.0038 0.4004 0.4278 0.042 Uiso 1 1 calc R . . 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 O 0.0283(10) 0.0197(10) 0.0265(10) 0.0032(8) 0.0075(8) -0.0066(8) N 0.0308(13) 0.0126(11) 0.0253(12) 0.0020(9) 0.0095(10) 0.0016(10) C1 0.0273(14) 0.0127(13) 0.0213(13) 0.0055(10) 0.0081(11) -0.0013(10) C2 0.0345(15) 0.0189(14) 0.0245(14) 0.0051(11) 0.0078(12) 0.0032(12) C3 0.054(2) 0.0214(15) 0.0321(16) 0.0042(12) 0.0159(15) 0.0128(14) C4 0.0457(19) 0.0336(18) 0.0465(19) 0.0138(15) 0.0225(16) 0.0176(15) C5 0.0267(15) 0.0321(17) 0.0482(19) 0.0101(15) 0.0065(14) 0.0022(13) C6 0.0306(15) 0.0172(13) 0.0325(15) 0.0023(12) 0.0081(12) -0.0018(11) C7 0.0235(13) 0.0179(13) 0.0197(13) -0.0010(10) 0.0057(11) -0.0033(11) C8 0.0255(14) 0.0164(13) 0.0203(13) 0.0004(10) 0.0075(11) 0.0003(11) C9 0.0286(14) 0.0115(12) 0.0227(13) 0.0003(10) 0.0064(11) 0.0006(10) C10 0.0406(16) 0.0160(13) 0.0278(15) 0.0006(11) 0.0172(13) -0.0017(12) C11 0.0329(15) 0.0109(12) 0.0292(14) 0.0034(11) 0.0128(12) -0.0024(11) C12 0.0335(16) 0.0233(15) 0.0518(19) -0.0010(14) 0.0187(14) 0.0006(13) C13 0.0270(16) 0.0342(18) 0.062(2) 0.0052(16) 0.0007(15) -0.0024(14) C14 0.050(2) 0.0242(16) 0.0360(17) -0.0013(13) 0.0015(15) -0.0118(14) C15 0.0467(18) 0.0197(14) 0.0328(16) -0.0034(12) 0.0150(14) -0.0022(13) C16 0.0317(15) 0.0166(13) 0.0318(15) 0.0001(12) 0.0094(12) 0.0009(12) C17 0.0305(15) 0.0218(14) 0.0341(15) 0.0013(12) 0.0135(12) 0.0031(12) _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 O H0 0.92(4) . ? O C7 1.436(3) . ? N H1 0.88(3) . ? N C9 1.468(3) . ? N C10 1.468(3) . ? C1 C2 1.393(4) . ? C1 C6 1.383(4) . ? C1 C7 1.522(3) . ? C2 H2 0.9301 . ? C2 C3 1.377(4) . ? C3 H3 0.9301 . ? C3 C4 1.380(4) . ? C4 H4 0.9300 . ? C4 C5 1.388(4) . ? C5 H5 0.9299 . ? C5 C6 1.386(4) . ? C6 H6 0.9300 . ? C7 H7 0.9800 . ? C7 C8 1.528(3) . ? C8 H8 0.9800 . ? C8 C9 1.525(3) . ? C8 C17 1.529(3) . ? C9 H9A 0.9701 . ? C9 H9B 0.9700 . ? C10 H10A 0.9698 . ? C10 H10B 0.9700 . ? C10 C11 1.512(4) . ? C11 C12 1.381(4) . ? C11 C16 1.397(4) . ? C12 H12 0.9299 . ? C12 C13 1.384(4) . ? C13 H13 0.9299 . ? C13 C14 1.382(5) . ? C14 H14 0.9300 . ? C14 C15 1.380(4) . ? C15 H15 0.9300 . ? C15 C16 1.377(4) . ? C16 H16 0.9301 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? 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 C7 O H0 104(2) . . ? C9 N H1 110(2) . . ? C10 N H1 110(2) . . ? C10 N C9 113.4(2) . . ? C2 C1 C7 120.4(2) . . ? C6 C1 C2 118.3(2) . . ? C6 C1 C7 121.2(2) . . ? C1 C2 H2 119.3 . . ? C3 C2 C1 121.3(3) . . ? C3 C2 H2 119.3 . . ? C2 C3 H3 120.1 . . ? C2 C3 C4 119.9(3) . . ? C4 C3 H3 120.0 . . ? C3 C4 H4 120.3 . . ? C3 C4 C5 119.5(3) . . ? C5 C4 H4 120.2 . . ? C4 C5 H5 119.9 . . ? C6 C5 C4 120.2(3) . . ? C6 C5 H5 119.9 . . ? C1 C6 C5 120.7(3) . . ? C1 C6 H6 119.7 . . ? C5 C6 H6 119.7 . . ? O C7 C1 110.2(2) . . ? O C7 H7 108.2 . . ? O C7 C8 107.52(19) . . ? C1 C7 H7 108.4 . . ? C1 C7 C8 113.9(2) . . ? C8 C7 H7 108.4 . . ? C7 C8 H8 108.2 . . ? C7 C8 C17 110.6(2) . . ? C9 C8 C7 110.50(19) . . ? C9 C8 H8 108.1 . . ? C9 C8 C17 111.2(2) . . ? C17 C8 H8 108.1 . . ? N C9 C8 112.0(2) . . ? N C9 H9A 109.2 . . ? N C9 H9B 109.3 . . ? C8 C9 H9A 109.2 . . ? C8 C9 H9B 109.2 . . ? H9A C9 H9B 107.9 . . ? N C10 H10A 108.3 . . ? N C10 H10B 108.4 . . ? N C10 C11 115.7(2) . . ? H10A C10 H10B 107.4 . . ? C11 C10 H10A 108.4 . . ? C11 C10 H10B 108.4 . . ? C12 C11 C10 121.1(2) . . ? C12 C11 C16 118.1(2) . . ? C16 C11 C10 120.8(2) . . ? C11 C12 H12 119.4 . . ? C11 C12 C13 121.1(3) . . ? C13 C12 H12 119.5 . . ? C12 C13 H13 119.9 . . ? C14 C13 C12 120.2(3) . . ? C14 C13 H13 119.9 . . ? C13 C14 H14 120.3 . . ? C15 C14 C13 119.4(3) . . ? C15 C14 H14 120.3 . . ? C14 C15 H15 119.9 . . ? C16 C15 C14 120.3(3) . . ? C16 C15 H15 119.9 . . ? C11 C16 H16 119.5 . . ? C15 C16 C11 121.0(3) . . ? C15 C16 H16 119.5 . . ? C8 C17 H17A 109.5 . . ? C8 C17 H17B 109.5 . . ? C8 C17 H17C 109.5 . . ? H17A C17 H17B 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? 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 O H0 N 0.92(4) 1.86(4) 2.771(3) 168(4) 4_566 N H1 O 0.88(3) 2.38(3) 3.078(3) 137(3) 2 #===END