# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2005 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Troels Skrydstrup' _publ_contact_author_address ; Department of Chemistry University of Aarhus Langelandsgade 140 Aarhus 8000 C DENMARK ; _publ_contact_author_email TS@CHEM.AU.DK _publ_section_title ; Samarium diiodide-induced intramolecular pinacol coupling of dinitrones: Synthesis of cyclic cis-vicinal diamines ; _publ_section_references ; Altomare,A., Cascarano,G., Giacovazzo,C., Guagliardi,A., Moliterni,.A,G,G., Burla,M.C., Polidori,G., Camalli,M. & Spagna,R. (1997). SIR97. University of Bari, Italy. Bruker (2003. SAINT. Version 7.06a. Bruker AXS Inc., Madison, Wisconsin, U.S.A. Bruker-Nonius (2003). APEX2. Version 1.0-6. Bruker-Nonius BV, Delft, Thw Netherlands. Burnett,M.N. & Johnson,C.K. (1996). ORTEP-III. Report ORNL-6895. Oak Ridge National Laboratory, Tennessee, USA. Sheldrick,G.M. (2003) SADABS. Version 2.10. Bruker AXS Inc., Madison, Wisconsin, USA. ; loop_ _publ_author_name 'Troels Skrydstrup' 'Jean-Philippe Ebran' 'Rita G. Hazel' #============================================================================== data_cmpd-9b _database_code_depnum_ccdc_archive 'CCDC 280862' #==================================== # 5. CHEMICAL DATA _chemical_name_systematic ; insert name here ; _chemical_name_common 'insert name here' _chemical_formula_sum 'C20 H22 N2 O' _chemical_formula_moiety 'C20 H22 N2 O' _chemical_formula_weight 306.40 _chemical_melting_point ? _chemical_compound_source ? #==================================== # 6. CRYSTAL DATA _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'C m c 21' _symmetry_space_group_name_Hall 'C 2c -2' loop_ _symmetry_equiv_pos_as_xyz +x,+y,+z -x,-y,1/2+z +x,-y,1/2+z -x,+y,+z 1/2+x,1/2+y,+z 1/2-x,1/2-y,1/2+z 1/2+x,1/2-y,1/2+z 1/2-x,1/2+y,+z _cell_length_a 20.478(2) _cell_length_b 8.647(1) _cell_length_c 9.235(1) _cell_angle_alpha 90.000 _cell_angle_beta 90.000 _cell_angle_gamma 90.000 _cell_volume 1635.3(3) _cell_formula_units_Z 4 _cell_measurement_temperature 100 _cell_measurement_reflns_used 3497 _cell_measurement_theta_min 2.56 _cell_measurement_theta_max 34.35 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.56 _exptl_crystal_size_mid 0.42 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.245 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 656 _exptl_absorpt_coefficient_mu 0.077 _exptl_absorpt_correction_type none _exptl_absorpt_process_details none #==================================== # 7. EXPERIMENTAL DATA _diffrn_ambient_temperature 100 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'x-ray tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device ; Bruker-Nonius X8Apex-II CCD diffractometer ; _diffrn_measurement_method ; Thin-slice \w and \f scans ; _diffrn_standards_decay_% 0 _diffrn_reflns_number 16485 _diffrn_reflns_av_R_equivalents 0.075 _diffrn_reflns_limit_h_min -32 _diffrn_reflns_limit_h_max 32 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.56 _diffrn_reflns_theta_max 34.35 _diffrn_reflns_reduction_process 16485 _reflns_number_total 1845 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measured_fraction_theta_full 0.999 _diffrn_reflns_theta_full 34.35 _reflns_number_gt 1316 _reflns_threshold_expression 'I> 3.\s(I) ' _computing_data_collection 'Apex2 (Bruker-Nonius, 2003 )' _computing_cell_refinement 'SAINT (Bruker, 2003)' _computing_data_reduction 'SAINT (Bruker, 2003)' _computing_structure_solution ; SIR97 (Altomare et al., 1997 ) , KRYSTAL ; _computing_structure_refinement 'modified ORFLS(1962), KRYSTAL' _computing_molecular_graphics ; ORTEP-III (Burnett & Johnson, 1996), KRYSTAL ; _computing_publication_material KRYSTAL _atom_type_scat_source IntTabIV #==================================== # 8. REFINEMENT DATA _refine_special_details ; ; _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; w= 1/{[\s~cs~(F^2^)+B+(1+A)F^2^]^1/2^- |F|}^2^ where A = 0.0300 and B = 0.00 ; _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 1316 _refine_ls_number_parameters 108 _refine_ls_number_restraints 0 _refine_ls_number_constraints 0 _refine_ls_R_factor_gt 0.037 _refine_ls_wR_factor_ref 0.043 _refine_ls_goodness_of_fit_ref 1.160 _refine_ls_shift/su_max 0.00013 _refine_ls_shift/su_mean 0.00003 _refine_diff_density_max 0.13(2) _refine_diff_density_min -0.15(2) #========================================== # 9. ATOMIC COORDINATES AND THERMAL PARAMETERS loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_thermal_displace_type O 0.50000 0.2791(2) 0.3341 0.0198(9) Uij N 0.44618(8) 0.0837(1) 0.4566(2) 0.0169(7) Uij C1 0.50000 0.1618(3) 0.4092(2) 0.0155(10) Uij C2 0.46218(10) -0.0412(2) 0.5565(2) 0.0165(7) Uij C3 0.44173(11) -0.2010(2) 0.4986(2) 0.0219(9) Uij C4 0.50000 -0.2534(3) 0.4083(3) 0.0228(13) Uij C5 0.38072(10) 0.1421(2) 0.4385(2) 0.0187(8) Uij C6 0.35631(10) 0.2327(2) 0.5682(2) 0.0178(7) Uij C7 0.30151(11) 0.1855(2) 0.6454(2) 0.0229(9) Uij C8 0.28008(12) 0.2691(2) 0.7649(2) 0.0271(10) Uij C9 0.31388(11) 0.4003(2) 0.8085(2) 0.0252(9) Uij C10 0.36843(11) 0.4479(2) 0.7331(2) 0.0237(10) Uij C11 0.38953(11) 0.3653(2) 0.6126(2) 0.0213(9) Uij H2 0.4450 -0.0225 0.6504 0.020 Uiso H3a 0.4339 -0.2709 0.5760 0.026 Uiso H3b 0.4036 -0.1931 0.4404 0.026 Uiso H4a 0.5000 -0.3625 0.3962 0.027 Uiso H4b 0.5000 -0.2049 0.3160 0.027 Uiso H5a 0.3800 0.2079 0.3562 0.022 Uiso H5b 0.3522 0.0570 0.4230 0.022 Uiso H7 0.2785 0.0953 0.6162 0.028 Uiso H8 0.2423 0.2367 0.8164 0.033 Uiso H9 0.2995 0.4573 0.8905 0.030 Uiso H10 0.3916 0.5372 0.7634 0.028 Uiso H11 0.4268 0.3994 0.5602 0.026 Uiso loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 O 0.0248(12) 0.0173(8) 0.0173(6) -0.0000 0.0000 0.0043(5) N 0.0183(9) 0.0150(6) 0.0174(4) 0.0014(6) 0.0000(5) 0.0033(4) C1 0.0185(14) 0.0173(10) 0.0109(6) -0.0000 0.0000 -0.0018(6) C2 0.0228(10) 0.0142(6) 0.0124(4) -0.0002(7) 0.0009(5) 0.0006(4) C3 0.0244(12) 0.0166(7) 0.0245(6) -0.0031(8) -0.0019(6) -0.0003(5) C4 0.0311(19) 0.0152(11) 0.0221(8) -0.0000 0.0000 -0.0034(7) C5 0.0174(11) 0.0202(7) 0.0183(5) 0.0014(7) -0.0015(5) -0.0000(5) C6 0.0180(10) 0.0183(7) 0.0170(5) 0.0042(7) -0.0012(5) 0.0016(5) C7 0.0181(12) 0.0255(9) 0.0251(6) -0.0011(8) 0.0009(6) -0.0010(6) C8 0.0208(12) 0.0332(10) 0.0272(7) 0.0043(9) 0.0057(6) -0.0007(6) C9 0.0287(12) 0.0243(9) 0.0226(6) 0.0091(9) 0.0032(6) -0.0005(6) C10 0.0331(13) 0.0156(8) 0.0224(6) 0.0024(8) -0.0002(7) -0.0003(5) C11 0.0254(12) 0.0181(7) 0.0205(6) 0.0001(8) 0.0022(6) 0.0019(5) #================================= # 10. MOLECULAR GEOMETRY loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 O C1 1.229(3) . . N C1 1.365(2) . . N C5 1.442(3) . . N C2 1.457(2) . . C2 C3 1.540(2) . . C2 C2 1.549(4) . 4_655 C3 C4 1.525(2) . . C5 C6 1.516(2) . . C6 C7 1.391(3) . . C6 C11 1.395(2) . . C7 C8 1.390(2) . . C8 C9 1.389(3) . . C9 C10 1.379(3) . . C10 C11 1.391(2) . . C2 H2 0.95 . . C3 H3a 0.95 . . C3 H3b 0.95 . . C4 H4a 0.95 . . C4 H4b 0.95 . . C5 H5a 0.95 . . C5 H5b 0.95 . . C7 H7 0.95 . . C8 H8 0.95 . . C9 H9 0.95 . . C10 H10 0.95 . . C11 H11 0.95 . . 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_2 _geom_angle_site_symmetry_3 C5 N C1 122.7(1) . . . C2 N C1 112.8(2) . . . C2 N C5 122.8(1) . . . N C1 O 126.13(9) . . . N C1 O 126.13(9) 4_655 . . N C1 N 107.7(2) 4_655 . . C3 C2 N 112.6(1) . . . C2 C2 N 103.0(1) 4_655 . . C2 C2 C3 105.8(1) 4_655 . . C2 C3 C4 104.1(2) . . . C3 C4 C3 103.0(2) 4_655 . . C6 C5 N 113.3(1) . . . C11 C6 C7 118.9(1) . . . C5 C6 C7 121.3(2) . . . C5 C6 C11 119.8(2) . . . C6 C7 C8 120.6(2) . . . C7 C8 C9 119.9(2) . . . C8 C9 C10 120.0(2) . . . C11 C10 C9 120.2(2) . . . C6 C11 C10 120.4(2) . . . N C2 H2 111.7 . . . C3 C2 H2 111.7 . . . C2 C2 H2 111.7 4_655 . . H3b C3 H3a 109.5 . . . C4 C3 H3a 110.8 . . . C2 C3 H3a 110.8 . . . C4 C3 H3b 110.8 . . . C2 C3 H3b 110.8 . . . H4b C4 H4a 109.5 . . . C3 C4 H4a 111.1 . . . C3 C4 H4a 111.1 4_655 . . C3 C4 H4b 111.1 . . . C3 C4 H4b 111.1 4_655 . . H5b C5 H5a 109.5 . . . N C5 H5a 108.5 . . . C6 C5 H5a 108.5 . . . N C5 H5b 108.5 . . . C6 C5 H5b 108.5 . . . C8 C7 H7 119.7 . . . C6 C7 H7 119.7 . . . C9 C8 H8 120.1 . . . C7 C8 H8 120.0 . . . C10 C9 H9 120.0 . . . C8 C9 H9 120.0 . . . C9 C10 H10 119.9 . . . C11 C10 H10 119.9 . . . C10 C11 H11 119.8 . . . C6 C11 H11 119.8 . . . #============================================================================== data_cmpd-9l _database_code_depnum_ccdc_archive 'CCDC 280863' #==================================== # 5. CHEMICAL DATA _chemical_name_systematic ; ; _chemical_formula_sum 'C22 H26 N2 O' _chemical_formula_moiety 'C22 H26 N2 O' _chemical_formula_weight 334.45 _chemical_melting_point ? _chemical_compound_source ? #==================================== # 6. CRYSTAL DATA _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'A b a 2' _symmetry_space_group_name_Hall 'A 2 -2ac' loop_ _symmetry_equiv_pos_as_xyz +x,+y,+z -x,-y,+z 1/2+x,1/2-y,+z 1/2-x,1/2+y,+z +x,1/2+y,1/2+z -x,1/2-y,1/2+z 1/2+x,-y,1/2+z 1/2-x,+y,1/2+z _cell_length_a 12.1490(4) _cell_length_b 20.4254(9) _cell_length_c 7.2291(3) _cell_angle_alpha 90.000 _cell_angle_beta 90.000 _cell_angle_gamma 90.000 _cell_volume 1793.89(12) _cell_formula_units_Z 4 _cell_measurement_temperature 100 _cell_measurement_reflns_used 9651 _cell_measurement_theta_min 1.99 _cell_measurement_theta_max 33.12 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max .34 _exptl_crystal_size_mid .32 _exptl_crystal_size_min .05 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.238 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 720 _exptl_absorpt_coefficient_mu 0.076 _exptl_absorpt_correction_type none _exptl_absorpt_process_details none #==================================== # 7. EXPERIMENTAL DATA _diffrn_ambient_temperature 100 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'x-ray tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device ; Bruker-Nonius X8Apex-II CCD diffractometer ; _diffrn_measurement_method ; Thin-slice \w and \f scans ; _diffrn_standards_decay_% 0 _diffrn_reflns_number 23313 _diffrn_reflns_av_R_equivalents 0.051 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -31 _diffrn_reflns_limit_k_max 31 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 1.99 _diffrn_reflns_theta_max 33.12 _diffrn_reflns_reduction_process 23313 _reflns_number_total 1826 _diffrn_measured_fraction_theta_max 1.000 _diffrn_measured_fraction_theta_full 1.000 _diffrn_reflns_theta_full 33.12 _reflns_number_gt 1590 _reflns_threshold_expression 'I> 3.\s(I) ' _computing_data_collection 'Apex2 (Bruker-Nonius, 2003 )' _computing_cell_refinement 'SAINT (Bruker, 2003)' _computing_data_reduction 'SAINT (Bruker, 2003)' _computing_structure_solution ; SIR97 (Altomare et al., 1997 ) , KRYSTAL ; _computing_structure_refinement 'modified ORFLS(1962), KRYSTAL' _computing_molecular_graphics ; ORTEP-III (Burnett & Johnson, 1996), KRYSTAL ; _computing_publication_material KRYSTAL _atom_type_scat_source IntTabIV #==================================== # 8. REFINEMENT DATA _refine_special_details ; ; _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; w= 1/{[\s~cs~(F^2^)+B+(1+A)F^2^]^1/2^- |F|}^2^ where A = 0.0400 and B = 0.50 ; _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 1590 _refine_ls_number_parameters 115 _refine_ls_number_restraints 0 _refine_ls_number_constraints 0 _refine_ls_R_factor_gt 0.042 _refine_ls_wR_factor_ref 0.050 _refine_ls_goodness_of_fit_ref 1.183 _refine_ls_shift/su_max 0.00050 _refine_ls_shift/su_mean 0.00007 _refine_diff_density_max 0.26(4) _refine_diff_density_min -0.19(4) #========================================== # 9. ATOMIC COORDINATES AND THERMAL PARAMETERS loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_thermal_displace_type _atom_site_occupancy O 0.0000 0.00000 -0.1141 0.0369(11) Uij 1.0 N 0.0219(1) 0.05250(6) 0.1651(3) 0.0238(6) Uij 1.0 C1 0.0000 0.00000 0.0555(4) 0.0235(10) Uij 1.0 C2 0.0047(3) 0.03711(15) 0.3652(5) 0.0138(6) Uiso 0.5 C3 0.1176(3) 0.03603(17) 0.4636(6) 0.0248(6) Uiso 0.5 C4 0.1573(3) -0.03599(17) 0.4414(6) 0.0299(16) Uij 0.5 C5 0.0495(4) -0.07575(20) 0.4736(7) 0.0246(9) Uiso 0.5 C6 -0.0369(3) -0.03692(16) 0.3618(6) 0.0175(7) Uiso 0.5 C7 -0.0752(4) 0.08277(19) 0.4597(7) 0.0244(9) Uiso 0.5 C8 -0.1512(3) -0.04742(18) 0.4337(6) 0.0274(7) Uiso 0.5 C9 0.0584(1) 0.11482(8) 0.0900(4) 0.0265(8) Uij 1.0 C10 -0.0324(1) 0.16528(7) 0.0649(3) 0.0196(6) Uij 1.0 C11 -0.0217(1) 0.22784(7) 0.1400(3) 0.0222(7) Uij 1.0 C12 -0.1039(2) 0.27429(7) 0.1125(3) 0.0256(7) Uij 1.0 C13 -0.1960(1) 0.25931(8) 0.0090(4) 0.0269(8) Uij 1.0 C14 -0.2072(1) 0.19698(8) -0.0671(4) 0.0255(7) Uij 1.0 C15 -0.1256(1) 0.15045(7) -0.0387(4) 0.0231(7) Uij 1.0 H3a 0.1105 0.0472 0.5901 0.046 Uiso 0.5 H3b 0.1677 0.0654 0.4053 0.046 Uiso 0.5 H4a 0.2115 -0.0469 0.5303 0.037 Uiso 0.5 H4b 0.1856 -0.0437 0.3203 0.037 Uiso 0.5 H5a 0.0307 -0.0768 0.6012 0.032 Uiso 0.5 H5b 0.0561 -0.1191 0.4283 0.032 Uiso 0.5 H7a -0.0859 0.0729 0.5868 0.029 Uiso 0.5 H7b -0.1439 0.0799 0.3982 0.029 Uiso 0.5 H7c -0.0474 0.1261 0.4501 0.029 Uiso 0.5 H8a -0.1760 -0.0916 0.4312 0.033 Uiso 0.5 H8b -0.2000 -0.0222 0.3594 0.033 Uiso 0.5 H8c -0.1537 -0.0325 0.5573 0.033 Uiso 0.5 H9a 0.0910 0.1069 -0.0278 0.032 Uiso 1.0 H9b 0.1121 0.1326 0.1710 0.032 Uiso 1.0 H11 0.0419 0.2388 0.2098 0.027 Uiso 1.0 H12 -0.0966 0.3166 0.1653 0.031 Uiso 1.0 H13 -0.2516 0.2914 -0.0102 0.033 Uiso 1.0 H14 -0.2704 0.1864 -0.1384 0.031 Uiso 1.0 H15 -0.1335 0.1080 -0.0908 0.028 Uiso 1.0 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 O 0.0635(14) 0.0310(9) 0.0160(8) 0.0089(9) 0.0000 0.0000 N 0.0411(8) 0.0149(5) 0.0154(6) -0.0001(5) 0.0003(6) 0.0018(5) C1 0.0325(12) 0.0193(9) 0.0185(10) 0.0050(8) 0.0000 0.0000 C4 0.0288(16) 0.0318(15) 0.0290(17) 0.0113(13) -0.0051(15) -0.0029(14) C9 0.0283(8) 0.0210(6) 0.0301(9) -0.0004(6) 0.0003(7) 0.0085(6) C10 0.0238(7) 0.0170(5) 0.0181(6) -0.0028(5) 0.0006(6) 0.0039(5) C11 0.0282(7) 0.0199(6) 0.0184(7) -0.0066(6) -0.0030(6) 0.0024(5) C12 0.0371(9) 0.0186(6) 0.0211(7) -0.0007(6) 0.0046(6) 0.0014(6) C13 0.0272(8) 0.0260(7) 0.0276(8) 0.0040(6) 0.0068(6) 0.0085(6) C14 0.0226(7) 0.0293(7) 0.0247(8) -0.0062(6) -0.0019(6) 0.0065(6) C15 0.0287(8) 0.0195(6) 0.0212(7) -0.0064(5) -0.0017(6) 0.0028(6) #================================= # 10. MOLECULAR GEOMETRY loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 O C1 1.226(3) . . N C1 1.359(2) . . N C9 1.453(2) . . N C6 1.469(4) 2_555 . N C2 1.495(4) . . C2 C7 1.509(6) . . C2 C3 1.546(5) . . C2 C6 1.594(4) . . C3 C4 1.556(5) . . C4 C5 1.559(6) . . C5 C6 1.544(6) . . C6 C8 1.498(6) . . C9 C10 1.520(2) . . C10 C15 1.391(2) . . C10 C11 1.395(2) . . C11 C12 1.392(2) . . C12 C13 1.380(3) . . C13 C14 1.393(2) . . C14 C15 1.389(2) . . C3 H3a 0.95 . . C3 H3b 0.95 . . C4 H4a 0.95 . . C4 H4b 0.95 . . C5 H5b 0.95 . . C5 H5a 0.95 . . C7 H7b 0.95 . . C7 H7c 0.95 . . C7 H7a 0.95 . . C8 H8c 0.95 . . C8 H8b 0.95 . . C8 H8a 0.95 . . C9 H9b 0.95 . . C9 H9a 0.95 . . C11 H11 0.95 . . C12 H12 0.95 . . C13 H13 0.95 . . C14 H14 0.95 . . C15 H15 0.95 . . 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_2 _geom_angle_site_symmetry_3 C9 N C1 122.2(1) . . . C6 N C1 114.7(2) 2_555 . . C2 N C1 111.8(2) . . . C6 N C9 120.9(2) 2_555 . . C2 N C9 126.0(2) . . . N C1 O 125.6(1) . . . N C1 N 108.7(2) 2_555 . . C7 C2 N 113.4(3) . . . C3 C2 N 108.9(3) . . . C6 C2 N 103.2(3) . . . C3 C2 C7 111.8(3) . . . C6 C2 C7 112.9(4) . . . C6 C2 C3 106.0(3) . . . C4 C3 C2 104.0(3) . . . C5 C4 C3 102.5(3) . . . C4 C5 C6 103.0(3) . . . C5 C6 C8 112.0(3) . . . C2 C6 C8 115.1(3) . . . C2 C6 C5 105.3(3) . . . C10 C9 N 114.6(1) . . . C11 C10 C15 119.0(1) . . . C9 C10 C15 120.5(1) . . . C9 C10 C11 120.5(1) . . . C10 C11 C12 120.1(2) . . . C11 C12 C13 120.5(1) . . . C14 C13 C12 119.7(2) . . . C13 C14 C15 119.8(2) . . . C10 C15 C14 120.8(1) . . . H3b C3 H3a 109.5 . . . C2 C3 H3a 111.1 . . . C4 C3 H3a 110.8 . . . C2 C3 H3b 110.8 . . . C4 C3 H3b 110.6 . . . H4b C4 H4a 109.5 . . . C3 C4 H4a 111.6 . . . C5 C4 H4a 111.2 . . . C3 C4 H4b 111.2 . . . C5 C4 H4b 110.7 . . . H5a C5 H5b 109.6 . . . C6 C5 H5b 110.9 . . . C4 C5 H5b 111.4 . . . C6 C5 H5a 110.8 . . . C4 C5 H5a 111.0 . . . H7c C7 H7b 109.7 . . . H7a C7 H7b 108.6 . . . C2 C7 H7b 108.4 . . . H7a C7 H7c 108.5 . . . C2 C7 H7c 108.3 . . . C2 C7 H7a 113.3 . . . H8b C8 H8c 109.8 . . . H8a C8 H8c 108.3 . . . C6 C8 H8c 108.2 . . . H8a C8 H8b 107.8 . . . C6 C8 H8b 107.7 . . . C6 C8 H8a 115.0 . . . H9a C9 H9b 109.3 . . . N C9 H9b 108.3 . . . C10 C9 H9b 108.2 . . . N C9 H9a 108.2 . . . C10 C9 H9a 108.1 . . . C12 C11 H11 120.0 . . . C10 C11 H11 119.9 . . . C13 C12 H12 119.7 . . . C11 C12 H12 119.8 . . . C12 C13 H13 120.1 . . . C14 C13 H13 120.2 . . . C15 C14 H14 120.1 . . . C13 C14 H14 120.0 . . . C14 C15 H15 119.6 . . . C10 C15 H15 119.7 . . .