Supplementary Material (ESI) for Perkin Transactions This journal is © The Royal Society of Chemistry 2001 data_global _journal_coden_Cambridge 207 _publ_requested_journal 'Perkin Transactions 1' loop_ _publ_author_name 'Nicoletti, Marcello' 'O Hagan, David' 'Slawin, A.' _publ_contact_author_name 'Prof David O Hagan' _publ_contact_author_address ; School of Chemistry University of St. Andrews North Haugh St. Andrews Fife KY16 9ST UNITED KINGDOM ; _publ_contact_author_email 'DO1@ST-ANDREWS.AC.UK' _publ_section_title ; The Asymmetric Bischler-Napieralski reaction: Preparation of 1,3,4-trisibtituted 1,2,3,4-tetrahydroisoquinolines ; data_12 _database_code_CSD 168569 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C19 H21 N' _chemical_formula_sum 'C19 H21 N' _chemical_formula_weight 263.37 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' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 5.9721(3) _cell_length_b 8.5759(4) _cell_length_c 30.5762(9) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1565.99(12) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 59 _cell_measurement_theta_min 12 _cell_measurement_theta_max 168 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max .1 _exptl_crystal_size_mid .1 _exptl_crystal_size_min .07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.117 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 568 _exptl_absorpt_coefficient_mu 0.064 _exptl_absorpt_correction_type sadabs _exptl_absorpt_correction_T_min 0.862945 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 0.9 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7903 _diffrn_reflns_av_R_equivalents 0.0709 _diffrn_reflns_av_sigmaI/netI 0.0669 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -33 _diffrn_reflns_limit_l_max 32 _diffrn_reflns_theta_min 2.47 _diffrn_reflns_theta_max 23.23 _reflns_number_total 2244 _reflns_number_gt 1739 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0292P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.055(4) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 7(4) _refine_ls_number_reflns 2244 _refine_ls_number_parameters 182 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0474 _refine_ls_R_factor_gt 0.0344 _refine_ls_wR_factor_ref 0.0678 _refine_ls_wR_factor_gt 0.0647 _refine_ls_goodness_of_fit_ref 0.872 _refine_ls_restrained_S_all 0.872 _refine_ls_shift/su_max 0.004 _refine_ls_shift/su_mean 0.001 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 0.5480(3) 0.9558(2) 0.05523(5) 0.0508(5) Uani 1 1 d . . . N2 N 0.4143(3) 0.87034(16) 0.07767(4) 0.0545(4) Uani 1 1 d . . . C3 C 0.2671(3) 0.94568(19) 0.10994(5) 0.0487(4) Uani 1 1 d . . . H3A H 0.1382 0.9873 0.0939 0.058 Uiso 1 1 calc R . . C4 C 0.3808(3) 1.08440(19) 0.13277(5) 0.0484(5) Uani 1 1 d . . . H4A H 0.5113 1.0427 0.1483 0.058 Uiso 1 1 calc R . . C5 C 0.4696(3) 1.1943(2) 0.09792(5) 0.0466(4) Uani 1 1 d . . . C6 C 0.5622(3) 1.12738(19) 0.06051(5) 0.0471(4) Uani 1 1 d . . . C7 C 0.6612(3) 1.2230(2) 0.02902(5) 0.0575(5) Uani 1 1 d . . . H7A H 0.7253 1.1790 0.0042 0.069 Uiso 1 1 calc R . . C8 C 0.6644(3) 1.3820(2) 0.03454(6) 0.0630(5) Uani 1 1 d . . . H8A H 0.7313 1.4449 0.0135 0.076 Uiso 1 1 calc R . . C9 C 0.5695(3) 1.4487(2) 0.07093(6) 0.0615(5) Uani 1 1 d . . . H9A H 0.5698 1.5565 0.0743 0.074 Uiso 1 1 calc R . . C10 C 0.4735(3) 1.3549(2) 0.10249(5) 0.0567(5) Uani 1 1 d . . . H10A H 0.4104 1.4003 0.1272 0.068 Uiso 1 1 calc R . . C11 C 0.6922(4) 0.8778(2) 0.02148(5) 0.0684(6) Uani 1 1 d . . . H11A H 0.6648 0.7675 0.0219 0.103 Uiso 1 1 calc R . . H11B H 0.8470 0.8973 0.0279 0.103 Uiso 1 1 calc R . . H11C H 0.6569 0.9187 -0.0069 0.103 Uiso 1 1 calc R . . C12 C 0.1770(3) 0.8215(2) 0.14160(5) 0.0586(5) Uani 1 1 d . . . H12A H 0.0802 0.8750 0.1627 0.070 Uiso 1 1 calc R . . C13 C 0.3629(3) 0.7428(2) 0.16738(6) 0.0736(6) Uani 1 1 d . . . H13A H 0.2994 0.6663 0.1866 0.110 Uiso 1 1 calc R . . H13B H 0.4420 0.8195 0.1842 0.110 Uiso 1 1 calc R . . H13C H 0.4647 0.6928 0.1475 0.110 Uiso 1 1 calc R . . C14 C 0.0339(4) 0.7020(2) 0.11804(7) 0.0807(6) Uani 1 1 d . . . H14A H -0.0196 0.6262 0.1386 0.121 Uiso 1 1 calc R . . H14B H 0.1219 0.6509 0.0960 0.121 Uiso 1 1 calc R . . H14C H -0.0911 0.7533 0.1045 0.121 Uiso 1 1 calc R . . C15 C 0.2354(3) 1.16331(18) 0.16658(5) 0.0495(5) Uani 1 1 d . . . C16 C 0.3033(3) 1.1735(2) 0.20959(5) 0.0662(6) Uani 1 1 d . . . H16A H 0.4385 1.1291 0.2181 0.079 Uiso 1 1 calc R . . C17 C 0.1714(4) 1.2497(3) 0.24038(6) 0.0882(7) Uani 1 1 d . . . H17A H 0.2192 1.2558 0.2693 0.106 Uiso 1 1 calc R . . C18 C -0.0271(4) 1.3153(3) 0.22858(7) 0.0858(7) Uani 1 1 d . . . H18A H -0.1140 1.3670 0.2493 0.103 Uiso 1 1 calc R . . C19 C -0.0978(3) 1.3050(2) 0.18625(7) 0.0726(6) Uani 1 1 d . . . H19A H -0.2340 1.3487 0.1781 0.087 Uiso 1 1 calc R . . C20 C 0.0318(3) 1.2303(2) 0.15567(6) 0.0624(5) Uani 1 1 d . . . H20A H -0.0183 1.2245 0.1269 0.075 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 C1 0.0572(12) 0.0510(11) 0.0444(10) 0.0011(9) -0.0010(9) 0.0004(11) N2 0.0644(10) 0.0506(9) 0.0484(8) -0.0019(7) 0.0018(8) -0.0050(8) C3 0.0483(10) 0.0476(10) 0.0501(9) 0.0015(8) 0.0016(9) -0.0017(9) C4 0.0500(11) 0.0498(11) 0.0456(9) 0.0010(8) -0.0017(8) -0.0015(9) C5 0.0431(10) 0.0484(11) 0.0483(10) 0.0009(8) -0.0039(8) -0.0028(9) C6 0.0466(11) 0.0470(10) 0.0477(9) -0.0006(8) 0.0004(9) -0.0034(9) C7 0.0563(12) 0.0587(13) 0.0576(11) 0.0024(9) 0.0097(9) -0.0009(11) C8 0.0675(14) 0.0529(12) 0.0687(12) 0.0099(10) 0.0114(11) -0.0087(11) C9 0.0648(14) 0.0467(10) 0.0731(12) 0.0017(11) 0.0071(12) -0.0052(10) C10 0.0609(13) 0.0554(12) 0.0539(11) -0.0061(9) 0.0010(10) -0.0051(10) C11 0.0870(16) 0.0568(11) 0.0613(11) -0.0037(9) 0.0151(11) 0.0044(12) C12 0.0638(12) 0.0516(11) 0.0605(11) 0.0048(9) 0.0087(10) -0.0021(10) C13 0.0943(16) 0.0643(13) 0.0621(11) 0.0118(10) -0.0016(12) -0.0006(12) C14 0.0808(14) 0.0658(14) 0.0956(14) 0.0123(12) -0.0017(13) -0.0227(13) C15 0.0543(12) 0.0484(10) 0.0456(9) 0.0002(8) 0.0025(9) -0.0065(9) C16 0.0673(13) 0.0804(14) 0.0510(10) -0.0021(10) -0.0033(10) -0.0020(12) C17 0.0951(18) 0.118(2) 0.0512(11) -0.0165(12) 0.0054(13) 0.0033(17) C18 0.0879(18) 0.1002(18) 0.0694(14) -0.0138(13) 0.0258(14) 0.0050(16) C19 0.0641(13) 0.0815(14) 0.0722(13) -0.0056(11) 0.0103(12) 0.0110(13) C20 0.0602(12) 0.0709(13) 0.0561(10) -0.0066(10) 0.0001(10) 0.0031(11) _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 N2 1.283(2) . ? C1 C6 1.483(2) . ? C1 C11 1.501(2) . ? N2 C3 1.471(2) . ? C3 C12 1.536(2) . ? C3 C4 1.538(2) . ? C4 C15 1.510(2) . ? C4 C5 1.518(2) . ? C5 C10 1.384(2) . ? C5 C6 1.394(2) . ? C6 C7 1.396(2) . ? C7 C8 1.374(2) . ? C8 C9 1.374(2) . ? C9 C10 1.381(2) . ? C12 C14 1.516(3) . ? C12 C13 1.520(2) . ? C15 C16 1.379(2) . ? C15 C20 1.385(2) . ? C16 C17 1.390(3) . ? C17 C18 1.361(3) . ? C18 C19 1.364(3) . ? C19 C20 1.372(2) . ? 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 N2 C1 C6 122.98(16) . . ? N2 C1 C11 118.03(16) . . ? C6 C1 C11 118.97(16) . . ? C1 N2 C3 118.68(14) . . ? N2 C3 C12 109.12(14) . . ? N2 C3 C4 112.35(14) . . ? C12 C3 C4 113.88(12) . . ? C15 C4 C5 113.77(14) . . ? C15 C4 C3 113.78(14) . . ? C5 C4 C3 108.43(12) . . ? C10 C5 C6 119.05(15) . . ? C10 C5 C4 123.55(15) . . ? C6 C5 C4 117.31(15) . . ? C5 C6 C7 119.46(15) . . ? C5 C6 C1 118.38(15) . . ? C7 C6 C1 122.15(15) . . ? C8 C7 C6 120.26(17) . . ? C7 C8 C9 120.49(17) . . ? C8 C9 C10 119.63(16) . . ? C9 C10 C5 121.08(17) . . ? C14 C12 C13 110.96(15) . . ? C14 C12 C3 111.48(14) . . ? C13 C12 C3 112.26(15) . . ? C16 C15 C20 117.47(17) . . ? C16 C15 C4 120.81(17) . . ? C20 C15 C4 121.72(15) . . ? C15 C16 C17 120.61(19) . . ? C18 C17 C16 120.54(19) . . ? C19 C18 C17 119.6(2) . . ? C18 C19 C20 120.16(19) . . ? C19 C20 C15 121.62(17) . . ? 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 C6 C1 N2 C3 0.4(2) . . . . ? C11 C1 N2 C3 -178.18(15) . . . . ? C1 N2 C3 C12 -163.26(15) . . . . ? C1 N2 C3 C4 -36.0(2) . . . . ? N2 C3 C4 C15 -179.24(13) . . . . ? C12 C3 C4 C15 -54.5(2) . . . . ? N2 C3 C4 C5 53.09(18) . . . . ? C12 C3 C4 C5 177.80(15) . . . . ? C15 C4 C5 C10 17.4(2) . . . . ? C3 C4 C5 C10 145.05(17) . . . . ? C15 C4 C5 C6 -166.05(15) . . . . ? C3 C4 C5 C6 -38.4(2) . . . . ? C10 C5 C6 C7 1.5(2) . . . . ? C4 C5 C6 C7 -175.23(16) . . . . ? C10 C5 C6 C1 -177.41(17) . . . . ? C4 C5 C6 C1 5.8(2) . . . . ? N2 C1 C6 C5 16.1(2) . . . . ? C11 C1 C6 C5 -165.34(16) . . . . ? N2 C1 C6 C7 -162.80(16) . . . . ? C11 C1 C6 C7 15.8(3) . . . . ? C5 C6 C7 C8 -1.0(3) . . . . ? C1 C6 C7 C8 177.89(17) . . . . ? C6 C7 C8 C9 -0.3(3) . . . . ? C7 C8 C9 C10 1.1(3) . . . . ? C8 C9 C10 C5 -0.5(3) . . . . ? C6 C5 C10 C9 -0.8(3) . . . . ? C4 C5 C10 C9 175.75(17) . . . . ? N2 C3 C12 C14 -63.0(2) . . . . ? C4 C3 C12 C14 170.55(15) . . . . ? N2 C3 C12 C13 62.18(18) . . . . ? C4 C3 C12 C13 -64.2(2) . . . . ? C5 C4 C15 C16 -114.07(18) . . . . ? C3 C4 C15 C16 121.07(16) . . . . ? C5 C4 C15 C20 64.8(2) . . . . ? C3 C4 C15 C20 -60.1(2) . . . . ? C20 C15 C16 C17 -0.5(3) . . . . ? C4 C15 C16 C17 178.39(18) . . . . ? C15 C16 C17 C18 0.0(3) . . . . ? C16 C17 C18 C19 0.6(4) . . . . ? C17 C18 C19 C20 -0.7(3) . . . . ? C18 C19 C20 C15 0.2(3) . . . . ? C16 C15 C20 C19 0.4(3) . . . . ? C4 C15 C20 C19 -178.51(16) . . . . ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 23.23 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.071 _refine_diff_density_min -0.076 _refine_diff_density_rms 0.020 data_14 _database_code_CSD 168570 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C24 H23 N' _chemical_formula_sum 'C24 H23 N' _chemical_formula_weight 325.43 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' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 9.4794(3) _cell_length_b 10.2277(3) _cell_length_c 19.5795(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1898.28(9) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 73 _cell_measurement_theta_min 12 _cell_measurement_theta_max 168 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max .1 _exptl_crystal_size_mid .1 _exptl_crystal_size_min .07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.139 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 696 _exptl_absorpt_coefficient_mu 0.065 _exptl_absorpt_correction_type sadabs _exptl_absorpt_correction_T_min 0.902814 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 0.9 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8352 _diffrn_reflns_av_R_equivalents 0.1259 _diffrn_reflns_av_sigmaI/netI 0.0903 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.08 _diffrn_reflns_theta_max 23.28 _reflns_number_total 2729 _reflns_number_gt 2014 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0375P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.020(2) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 1(5) _refine_ls_number_reflns 2729 _refine_ls_number_parameters 227 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0742 _refine_ls_R_factor_gt 0.0460 _refine_ls_wR_factor_ref 0.0869 _refine_ls_wR_factor_gt 0.0776 _refine_ls_goodness_of_fit_ref 0.957 _refine_ls_restrained_S_all 0.957 _refine_ls_shift/su_max 0.003 _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 0.1854(2) 0.8531(2) 0.18476(12) 0.0472(6) Uani 1 1 d . . . N2 N 0.0529(2) 0.86799(18) 0.17402(9) 0.0516(5) Uani 1 1 d . . . C3 C -0.0381(2) 0.8940(2) 0.23332(11) 0.0474(6) Uani 1 1 d . . . H3A H -0.0273 0.9867 0.2448 0.057 Uiso 1 1 calc R . . C4 C 0.0079(2) 0.8148(2) 0.29616(11) 0.0463(6) Uani 1 1 d . . . H4A H 0.0007 0.7223 0.2836 0.056 Uiso 1 1 calc R . . C5 C 0.1632(2) 0.8423(2) 0.30957(12) 0.0475(6) Uani 1 1 d . . . C6 C 0.2504(2) 0.8613(2) 0.25322(12) 0.0481(6) Uani 1 1 d . . . C7 C 0.3922(3) 0.8892(3) 0.26343(14) 0.0637(7) Uani 1 1 d . . . H7A H 0.4499 0.9059 0.2260 0.076 Uiso 1 1 calc R . . C8 C 0.4488(3) 0.8925(3) 0.32844(14) 0.0738(8) Uani 1 1 d . . . H8A H 0.5438 0.9114 0.3348 0.089 Uiso 1 1 calc R . . C9 C 0.3632(3) 0.8675(3) 0.38352(15) 0.0730(8) Uani 1 1 d . . . H9A H 0.4013 0.8665 0.4273 0.088 Uiso 1 1 calc R . . C10 C 0.2212(3) 0.8438(2) 0.37451(12) 0.0590(7) Uani 1 1 d . . . H10A H 0.1640 0.8287 0.4123 0.071 Uiso 1 1 calc R . . C11 C 0.2744(2) 0.8260(2) 0.12301(12) 0.0482(6) Uani 1 1 d . . . C12 C 0.2447(3) 0.8878(2) 0.06208(12) 0.0568(6) Uani 1 1 d . . . H12A H 0.1716 0.9483 0.0601 0.068 Uiso 1 1 calc R . . C13 C 0.3223(3) 0.8607(2) 0.00381(13) 0.0634(7) Uani 1 1 d . . . H13A H 0.3020 0.9040 -0.0368 0.076 Uiso 1 1 calc R . . C14 C 0.4295(3) 0.7700(3) 0.00588(14) 0.0638(7) Uani 1 1 d . . . H14A H 0.4815 0.7517 -0.0332 0.077 Uiso 1 1 calc R . . C15 C 0.4590(3) 0.7070(3) 0.06585(14) 0.0642(7) Uani 1 1 d . . . H15A H 0.5307 0.6451 0.0673 0.077 Uiso 1 1 calc R . . C16 C 0.3825(3) 0.7349(2) 0.12456(13) 0.0586(7) Uani 1 1 d . . . H16A H 0.4040 0.6922 0.1652 0.070 Uiso 1 1 calc R . . C17 C -0.1919(2) 0.8732(2) 0.21242(12) 0.0560(7) Uani 1 1 d . . . H17A H -0.2508 0.8939 0.2521 0.067 Uiso 1 1 calc R . . C18 C -0.2224(3) 0.7330(3) 0.19239(14) 0.0739(8) Uani 1 1 d . . . H18A H -0.3199 0.7249 0.1797 0.111 Uiso 1 1 calc R . . H18B H -0.2028 0.6764 0.2303 0.111 Uiso 1 1 calc R . . H18C H -0.1639 0.7089 0.1544 0.111 Uiso 1 1 calc R . . C19 C -0.2343(3) 0.9654(3) 0.15498(14) 0.0841(9) Uani 1 1 d . . . H19A H -0.3311 0.9502 0.1430 0.126 Uiso 1 1 calc R . . H19B H -0.1755 0.9500 0.1159 0.126 Uiso 1 1 calc R . . H19C H -0.2232 1.0543 0.1699 0.126 Uiso 1 1 calc R . . C20 C -0.0869(2) 0.8350(2) 0.35776(12) 0.0486(6) Uani 1 1 d . . . C21 C -0.0981(3) 0.9558(3) 0.38886(13) 0.0600(7) Uani 1 1 d . . . H21A H -0.0467 1.0260 0.3718 0.072 Uiso 1 1 calc R . . C22 C -0.1847(3) 0.9740(3) 0.44507(14) 0.0672(8) Uani 1 1 d . . . H22A H -0.1889 1.0551 0.4664 0.081 Uiso 1 1 calc R . . C23 C -0.2640(3) 0.8720(3) 0.46905(13) 0.0738(8) Uani 1 1 d . . . H23A H -0.3239 0.8844 0.5061 0.089 Uiso 1 1 calc R . . C24 C -0.2554(3) 0.7526(3) 0.43888(13) 0.0757(8) Uani 1 1 d . . . H24A H -0.3093 0.6835 0.4554 0.091 Uiso 1 1 calc R . . C25 C -0.1660(3) 0.7334(3) 0.38308(13) 0.0628(7) Uani 1 1 d . . . H25A H -0.1599 0.6513 0.3629 0.075 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 C1 0.0453(14) 0.0532(15) 0.0431(14) -0.0009(12) 0.0029(12) -0.0031(12) N2 0.0500(13) 0.0635(13) 0.0413(11) 0.0027(10) 0.0035(10) -0.0009(11) C3 0.0482(15) 0.0528(13) 0.0411(14) -0.0021(12) 0.0027(12) 0.0021(11) C4 0.0501(15) 0.0471(13) 0.0416(13) -0.0006(12) 0.0042(12) 0.0000(11) C5 0.0492(14) 0.0478(14) 0.0453(15) -0.0037(12) -0.0021(13) 0.0041(11) C6 0.0438(14) 0.0568(15) 0.0438(14) -0.0037(13) -0.0027(13) 0.0006(12) C7 0.0543(17) 0.0868(18) 0.0499(16) -0.0111(16) 0.0037(14) -0.0044(14) C8 0.0512(17) 0.110(2) 0.0604(18) -0.0176(18) -0.0095(16) -0.0058(17) C9 0.0656(19) 0.103(2) 0.0509(17) -0.0146(17) -0.0119(15) 0.0069(16) C10 0.0563(17) 0.0799(19) 0.0407(15) -0.0020(14) 0.0020(13) 0.0031(14) C11 0.0453(14) 0.0596(15) 0.0398(14) -0.0041(13) 0.0024(12) -0.0044(12) C12 0.0540(15) 0.0650(15) 0.0512(16) -0.0005(14) 0.0051(14) 0.0003(13) C13 0.0666(17) 0.0791(19) 0.0446(15) 0.0027(15) 0.0062(14) -0.0013(15) C14 0.0547(16) 0.0849(18) 0.0517(16) -0.0068(16) 0.0134(14) -0.0053(15) C15 0.0526(16) 0.0813(18) 0.0588(17) -0.0093(15) 0.0064(14) 0.0104(13) C16 0.0566(16) 0.0727(17) 0.0464(15) -0.0013(14) -0.0024(13) 0.0037(14) C17 0.0466(15) 0.0704(18) 0.0510(15) 0.0007(14) 0.0018(12) 0.0030(13) C18 0.0624(18) 0.086(2) 0.0728(18) -0.0025(17) -0.0140(15) -0.0107(15) C19 0.068(2) 0.100(2) 0.084(2) 0.0238(19) -0.0129(18) 0.0147(17) C20 0.0519(15) 0.0544(15) 0.0394(13) 0.0004(13) 0.0011(12) 0.0029(12) C21 0.0612(18) 0.0645(16) 0.0544(16) -0.0088(15) 0.0077(14) -0.0021(14) C22 0.0715(19) 0.0737(18) 0.0565(17) -0.0126(16) 0.0043(15) 0.0080(16) C23 0.078(2) 0.094(2) 0.0488(16) 0.0004(17) 0.0177(16) 0.0080(18) C24 0.092(2) 0.081(2) 0.0538(16) 0.0062(17) 0.0165(17) -0.0071(17) C25 0.0840(19) 0.0578(16) 0.0466(15) 0.0016(14) 0.0121(15) -0.0033(14) _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 N2 1.283(3) . ? C1 C6 1.478(3) . ? C1 C11 1.500(3) . ? N2 C3 1.470(3) . ? C3 C17 1.529(3) . ? C3 C4 1.536(3) . ? C4 C20 1.518(3) . ? C4 C5 1.521(3) . ? C5 C10 1.386(3) . ? C5 C6 1.393(3) . ? C6 C7 1.388(3) . ? C7 C8 1.382(3) . ? C8 C9 1.374(4) . ? C9 C10 1.379(3) . ? C11 C12 1.379(3) . ? C11 C16 1.385(3) . ? C12 C13 1.386(3) . ? C13 C14 1.376(3) . ? C14 C15 1.368(3) . ? C15 C16 1.389(3) . ? C17 C18 1.514(4) . ? C17 C19 1.522(3) . ? C20 C25 1.373(3) . ? C20 C21 1.381(3) . ? C21 C22 1.385(3) . ? C22 C23 1.369(4) . ? C23 C24 1.359(4) . ? C24 C25 1.397(4) . ? 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 N2 C1 C6 123.4(2) . . ? N2 C1 C11 116.2(2) . . ? C6 C1 C11 120.4(2) . . ? C1 N2 C3 117.78(19) . . ? N2 C3 C17 108.80(19) . . ? N2 C3 C4 111.76(18) . . ? C17 C3 C4 114.28(18) . . ? C20 C4 C5 114.3(2) . . ? C20 C4 C3 113.37(18) . . ? C5 C4 C3 108.38(18) . . ? C10 C5 C6 119.3(2) . . ? C10 C5 C4 123.0(2) . . ? C6 C5 C4 117.6(2) . . ? C7 C6 C5 119.3(2) . . ? C7 C6 C1 123.1(2) . . ? C5 C6 C1 117.6(2) . . ? C8 C7 C6 120.9(3) . . ? C9 C8 C7 119.3(2) . . ? C8 C9 C10 120.6(3) . . ? C9 C10 C5 120.4(3) . . ? C12 C11 C16 118.6(2) . . ? C12 C11 C1 119.8(2) . . ? C16 C11 C1 121.5(2) . . ? C11 C12 C13 120.8(2) . . ? C14 C13 C12 120.2(3) . . ? C15 C14 C13 119.6(3) . . ? C14 C15 C16 120.5(3) . . ? C11 C16 C15 120.4(2) . . ? C18 C17 C19 110.2(2) . . ? C18 C17 C3 112.6(2) . . ? C19 C17 C3 111.3(2) . . ? C25 C20 C21 118.4(2) . . ? C25 C20 C4 120.5(2) . . ? C21 C20 C4 121.1(2) . . ? C20 C21 C22 121.1(3) . . ? C23 C22 C21 119.7(3) . . ? C24 C23 C22 120.2(3) . . ? C23 C24 C25 120.2(3) . . ? C20 C25 C24 120.5(3) . . ? 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 C6 C1 N2 C3 -0.2(3) . . . . ? C11 C1 N2 C3 179.7(2) . . . . ? C1 N2 C3 C17 -165.48(19) . . . . ? C1 N2 C3 C4 -38.4(3) . . . . ? N2 C3 C4 C20 -177.7(2) . . . . ? C17 C3 C4 C20 -53.6(3) . . . . ? N2 C3 C4 C5 54.3(2) . . . . ? C17 C3 C4 C5 178.4(2) . . . . ? C20 C4 C5 C10 19.9(3) . . . . ? C3 C4 C5 C10 147.4(2) . . . . ? C20 C4 C5 C6 -162.8(2) . . . . ? C3 C4 C5 C6 -35.3(3) . . . . ? C10 C5 C6 C7 -3.8(4) . . . . ? C4 C5 C6 C7 178.7(2) . . . . ? C10 C5 C6 C1 177.3(2) . . . . ? C4 C5 C6 C1 -0.1(3) . . . . ? N2 C1 C6 C7 -157.6(2) . . . . ? C11 C1 C6 C7 22.5(3) . . . . ? N2 C1 C6 C5 21.2(3) . . . . ? C11 C1 C6 C5 -158.7(2) . . . . ? C5 C6 C7 C8 2.9(4) . . . . ? C1 C6 C7 C8 -178.3(2) . . . . ? C6 C7 C8 C9 0.1(5) . . . . ? C7 C8 C9 C10 -2.2(5) . . . . ? C8 C9 C10 C5 1.3(4) . . . . ? C6 C5 C10 C9 1.8(4) . . . . ? C4 C5 C10 C9 179.1(2) . . . . ? N2 C1 C11 C12 37.8(3) . . . . ? C6 C1 C11 C12 -142.3(2) . . . . ? N2 C1 C11 C16 -139.0(2) . . . . ? C6 C1 C11 C16 40.9(3) . . . . ? C16 C11 C12 C13 -0.8(4) . . . . ? C1 C11 C12 C13 -177.7(2) . . . . ? C11 C12 C13 C14 0.9(4) . . . . ? C12 C13 C14 C15 -0.2(4) . . . . ? C13 C14 C15 C16 -0.6(4) . . . . ? C12 C11 C16 C15 0.1(4) . . . . ? C1 C11 C16 C15 176.9(2) . . . . ? C14 C15 C16 C11 0.6(4) . . . . ? N2 C3 C17 C18 63.7(2) . . . . ? C4 C3 C17 C18 -62.0(3) . . . . ? N2 C3 C17 C19 -60.6(3) . . . . ? C4 C3 C17 C19 173.7(2) . . . . ? C5 C4 C20 C25 -120.3(2) . . . . ? C3 C4 C20 C25 114.8(2) . . . . ? C5 C4 C20 C21 60.9(3) . . . . ? C3 C4 C20 C21 -63.9(3) . . . . ? C25 C20 C21 C22 1.2(4) . . . . ? C4 C20 C21 C22 -180.0(2) . . . . ? C20 C21 C22 C23 -2.0(4) . . . . ? C21 C22 C23 C24 1.5(4) . . . . ? C22 C23 C24 C25 -0.2(4) . . . . ? C21 C20 C25 C24 0.1(4) . . . . ? C4 C20 C25 C24 -178.7(2) . . . . ? C23 C24 C25 C20 -0.6(4) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 23.28 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.170 _refine_diff_density_min -0.165 _refine_diff_density_rms 0.053