Supplementary Material (ESI) for Organic & Biomolecular Chemistry This journal is (c) The Royal Society of Chemistry 2006 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Jun-ichiro Setsune' _publ_contact_author_address ; Department of Chemistry Kobe University Nada-ku Kobe 657 JAPAN ; _publ_contact_author_email setsunej@kobe-u.ac.jp _publ_section_title ; Synthesis of Bis(azafulvene)s by Dehydration of Hydroxymethylpyrrole Derivatives ; loop_ _publ_author_name 'Jun-ichiro Setsune' 'Aya Tanabe' 'Junko Watanabe' 'Satoshi Maeda' # Attachment '6a-and-9.CIF' data_(6a) _database_code_depnum_ccdc_archive 'CCDC 294434' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 6,6f-diphenyl-3,3f,4,4f-tetraethyl-2,2f-bis(azafulvene) ; _chemical_name_common 6,6f-diphenyl-3,3f,4,4f-tetraethyl-2,2f-bis(azafulvene) _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C30 H32 N2' _chemical_formula_weight 420.58 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 Pbca 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' '-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 14.883(4) _cell_length_b 7.830(2) _cell_length_c 20.587(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2399.0(11) _cell_formula_units_Z 4 _cell_measurement_temperature 294(2) _cell_measurement_reflns_used 915 _cell_measurement_theta_min 2.406 _cell_measurement_theta_max 24.009 _exptl_crystal_description prism _exptl_crystal_colour orange _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.164 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 904 _exptl_absorpt_coefficient_mu 0.067 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details 'program SADABS ver. 2.03 (Sheldrick)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 294(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 ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11904 _diffrn_reflns_av_R_equivalents 0.0547 _diffrn_reflns_av_sigmaI/netI 0.0416 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 1.98 _diffrn_reflns_theta_max 26.96 _reflns_number_total 2409 _reflns_number_gt 1472 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SAINT+ ver. 6.45' _computing_cell_refinement 'Bruker SAINT+ ver. 6.45' _computing_data_reduction 'Bruker SAINT+ ver. 6.45' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker XSHELL ver. 4.02' _computing_publication_material 'Bruker SHELXTL ver. 6.14' _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^)+(0.0550P)^2^+0.2086P] 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 none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2409 _refine_ls_number_parameters 209 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0793 _refine_ls_R_factor_gt 0.0410 _refine_ls_wR_factor_ref 0.1167 _refine_ls_wR_factor_gt 0.0978 _refine_ls_goodness_of_fit_ref 1.010 _refine_ls_restrained_S_all 1.010 _refine_ls_shift/su_max 0.000 _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 0.48254(11) 0.07012(18) 0.51961(7) 0.0447(4) Uani 1 1 d . . . C2 C 0.40360(10) 0.17871(19) 0.50513(8) 0.0459(4) Uani 1 1 d . . . C3 C 0.39888(10) 0.29133(19) 0.55463(8) 0.0469(4) Uani 1 1 d . . . C4 C 0.47334(11) 0.25142(18) 0.59895(7) 0.0467(4) Uani 1 1 d . . . C5 C 0.49291(11) 0.3324(2) 0.65514(8) 0.0508(4) Uani 1 1 d . . . C6 C 0.56428(11) 0.3017(2) 0.70199(8) 0.0498(4) Uani 1 1 d . . . C7 C 0.56282(14) 0.3898(2) 0.76064(9) 0.0614(5) Uani 1 1 d . . . C8 C 0.62688(15) 0.3626(3) 0.80762(10) 0.0700(6) Uani 1 1 d . . . C9 C 0.69440(15) 0.2472(3) 0.79713(9) 0.0651(5) Uani 1 1 d . . . C10 C 0.69835(14) 0.1596(2) 0.73936(9) 0.0635(5) Uani 1 1 d . . . C11 C 0.63466(13) 0.1865(2) 0.69183(9) 0.0591(5) Uani 1 1 d . . . C12 C 0.34349(12) 0.1700(3) 0.44716(9) 0.0566(5) Uani 1 1 d . . . C13 C 0.38244(17) 0.2540(3) 0.38753(11) 0.0711(6) Uani 1 1 d . . . C14 C 0.33701(12) 0.4404(2) 0.56248(10) 0.0538(5) Uani 1 1 d . . . C15 C 0.37756(15) 0.6034(2) 0.53669(12) 0.0621(5) Uani 1 1 d . . . H5 H 0.4525(10) 0.428(2) 0.6671(7) 0.052(4) Uiso 1 1 d . . . H7 H 0.5132(13) 0.469(3) 0.7658(9) 0.075(6) Uiso 1 1 d . . . H8 H 0.6238(13) 0.425(3) 0.8473(10) 0.083(6) Uiso 1 1 d . . . H9 H 0.7407(13) 0.227(3) 0.8298(10) 0.081(6) Uiso 1 1 d . . . H10 H 0.7465(13) 0.076(2) 0.7310(9) 0.076(6) Uiso 1 1 d . . . H11 H 0.6382(12) 0.125(2) 0.6494(10) 0.074(5) Uiso 1 1 d . . . H12A H 0.3301(10) 0.044(2) 0.4371(8) 0.059(5) Uiso 1 1 d . . . H13A H 0.4423(17) 0.200(3) 0.3756(10) 0.102(8) Uiso 1 1 d . . . H14A H 0.2805(12) 0.419(2) 0.5385(8) 0.062(5) Uiso 1 1 d . . . H15A H 0.3906(13) 0.594(3) 0.4902(11) 0.087(7) Uiso 1 1 d . . . H12B H 0.2864(13) 0.225(2) 0.4573(9) 0.074(6) Uiso 1 1 d . . . H13B H 0.3449(15) 0.236(3) 0.3485(11) 0.092(7) Uiso 1 1 d . . . H14B H 0.3237(10) 0.460(2) 0.6075(9) 0.062(5) Uiso 1 1 d . . . H15B H 0.3370(13) 0.699(3) 0.5435(9) 0.073(6) Uiso 1 1 d . . . H13C H 0.3883(13) 0.378(3) 0.3945(10) 0.086(6) Uiso 1 1 d . . . H15C H 0.4366(16) 0.626(3) 0.5602(10) 0.091(7) Uiso 1 1 d . . . N1 N 0.52211(9) 0.11244(16) 0.57412(6) 0.0498(4) Uani 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 0.0575(10) 0.0350(8) 0.0416(9) 0.0037(6) 0.0053(7) -0.0011(7) C2 0.0497(9) 0.0392(8) 0.0488(9) 0.0041(7) 0.0052(7) -0.0015(7) C3 0.0510(10) 0.0383(8) 0.0514(10) 0.0035(7) 0.0081(7) 0.0002(7) C4 0.0605(10) 0.0359(8) 0.0439(9) 0.0019(7) 0.0081(7) 0.0021(7) C5 0.0631(11) 0.0394(9) 0.0499(10) 0.0004(7) 0.0099(8) 0.0036(8) C6 0.0632(11) 0.0403(8) 0.0461(9) 0.0037(7) 0.0050(7) -0.0038(8) C7 0.0770(13) 0.0549(11) 0.0522(11) -0.0062(8) 0.0057(9) 0.0009(10) C8 0.0902(15) 0.0717(13) 0.0481(11) -0.0088(10) -0.0015(10) -0.0080(12) C9 0.0761(13) 0.0635(12) 0.0557(12) 0.0084(9) -0.0051(10) -0.0117(11) C10 0.0691(13) 0.0582(11) 0.0633(12) 0.0033(9) -0.0032(10) 0.0013(10) C11 0.0699(12) 0.0552(10) 0.0523(11) -0.0057(9) 0.0006(9) 0.0060(9) C12 0.0475(10) 0.0582(12) 0.0640(12) -0.0077(9) -0.0017(8) 0.0040(9) C13 0.0828(16) 0.0715(15) 0.0591(13) 0.0079(11) -0.0124(11) 0.0042(12) C14 0.0498(11) 0.0500(10) 0.0617(12) -0.0029(9) 0.0057(9) 0.0050(8) C15 0.0634(13) 0.0426(10) 0.0803(15) 0.0026(10) 0.0007(11) 0.0073(10) N1 0.0646(9) 0.0386(7) 0.0462(8) 0.0015(6) 0.0016(6) 0.0061(6) _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 N1 1.310(2) . ? C1 C1 1.459(3) 5_656 ? C1 C2 1.481(2) . ? C2 C3 1.349(2) . ? C2 C12 1.493(2) . ? C3 C4 1.469(2) . ? C3 C14 1.496(2) . ? C4 C5 1.351(2) . ? C4 N1 1.4044(19) . ? C5 C6 1.455(2) . ? C6 C7 1.391(2) . ? C6 C11 1.398(3) . ? C7 C8 1.375(3) . ? C8 C9 1.368(3) . ? C9 C10 1.374(3) . ? C10 C11 1.378(3) . ? C12 C13 1.508(3) . ? C14 C15 1.508(3) . ? 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 N1 C1 C1 120.29(18) . 5_656 ? N1 C1 C2 112.58(13) . . ? C1 C1 C2 127.13(18) 5_656 . ? C3 C2 C1 105.34(14) . . ? C3 C2 C12 127.03(15) . . ? C1 C2 C12 127.61(14) . . ? C2 C3 C4 106.90(13) . . ? C2 C3 C14 128.59(16) . . ? C4 C3 C14 124.28(15) . . ? C5 C4 N1 124.33(15) . . ? C5 C4 C3 126.48(15) . . ? N1 C4 C3 109.19(13) . . ? C4 C5 C6 130.34(16) . . ? C7 C6 C11 117.49(17) . . ? C7 C6 C5 118.82(16) . . ? C11 C6 C5 123.69(15) . . ? C8 C7 C6 121.52(19) . . ? C9 C8 C7 120.06(19) . . ? C8 C9 C10 119.83(19) . . ? C9 C10 C11 120.6(2) . . ? C10 C11 C6 120.52(18) . . ? C2 C12 C13 113.61(16) . . ? C3 C14 C15 112.09(15) . . ? C1 N1 C4 105.99(13) . . ? _diffrn_measured_fraction_theta_max 0.927 _diffrn_reflns_theta_full 26.96 _diffrn_measured_fraction_theta_full 0.927 _refine_diff_density_max 0.153 _refine_diff_density_min -0.157 _refine_diff_density_rms 0.038 #===END data_(9) _database_code_depnum_ccdc_archive 'CCDC 294435' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 6,6f-Diphenyl-2,2f-bis(azafulvenyl)-gem-dimethylmethane ; _chemical_name_common 6,6f-Diphenyl-2,2f-bis(azafulvenyl)-gem-dimethylmethane _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C25 H22 N2' _chemical_formula_weight 350.45 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 Fdd2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' 'x+1/4, -y+1/4, z+1/4' '-x+1/4, y+1/4, z+1/4' 'x, y+1/2, z+1/2' '-x, -y+1/2, z+1/2' 'x+1/4, -y+3/4, z+3/4' '-x+1/4, y+3/4, z+3/4' 'x+1/2, y, z+1/2' '-x+1/2, -y, z+1/2' 'x+3/4, -y+1/4, z+3/4' '-x+3/4, y+1/4, z+3/4' 'x+1/2, y+1/2, z' '-x+1/2, -y+1/2, z' 'x+3/4, -y+3/4, z+1/4' '-x+3/4, y+3/4, z+1/4' _cell_length_a 17.135(3) _cell_length_b 38.228(8) _cell_length_c 6.1877(12) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 4053.1(14) _cell_formula_units_Z 8 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 632 _cell_measurement_theta_min 3.194 _cell_measurement_theta_max 20.226 _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.149 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1488 _exptl_absorpt_coefficient_mu 0.067 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details 'program SADABS ver. 2.03 (Sheldrick)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(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 ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5681 _diffrn_reflns_av_R_equivalents 0.0313 _diffrn_reflns_av_sigmaI/netI 0.0455 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -28 _diffrn_reflns_limit_k_max 47 _diffrn_reflns_limit_l_min -7 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_theta_min 2.13 _diffrn_reflns_theta_max 27.31 _reflns_number_total 2076 _reflns_number_gt 1359 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SAINT+ ver. 6.45' _computing_cell_refinement 'Bruker SAINT+ ver. 6.45' _computing_data_reduction 'Bruker SAINT+ ver. 6.45' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker XSHELL ver. 4.02' _computing_publication_material 'Bruker SHELXTL ver. 6.14' _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^)+(0.0467P)^2^+0.4669P] 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 none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -1(4) _refine_ls_number_reflns 2076 _refine_ls_number_parameters 167 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0750 _refine_ls_R_factor_gt 0.0393 _refine_ls_wR_factor_ref 0.1050 _refine_ls_wR_factor_gt 0.0894 _refine_ls_goodness_of_fit_ref 1.009 _refine_ls_restrained_S_all 1.008 _refine_ls_shift/su_max 0.000 _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 0.42971(10) 0.00177(5) 0.6047(3) 0.0569(5) Uani 1 1 d . . . C2 C 0.40798(13) -0.02539(6) 0.7582(4) 0.0691(6) Uani 1 1 d . . . C3 C 0.34603(13) -0.01351(6) 0.8653(5) 0.0717(6) Uani 1 1 d . . . C4 C 0.32894(11) 0.02083(5) 0.7792(3) 0.0581(5) Uani 1 1 d . . . C5 C 0.27170(11) 0.04235(6) 0.8486(4) 0.0664(6) Uani 1 1 d . . . C6 C 0.24845(11) 0.07671(6) 0.7717(4) 0.0655(6) Uani 1 1 d . . . C7 C 0.19883(16) 0.09639(7) 0.8976(6) 0.0917(8) Uani 1 1 d . . . C8 C 0.17549(19) 0.12919(8) 0.8337(8) 0.1150(12) Uani 1 1 d . . . C9 C 0.19986(17) 0.14249(8) 0.6387(7) 0.1034(10) Uani 1 1 d . . . C10 C 0.24842(17) 0.12323(7) 0.5140(5) 0.0905(8) Uani 1 1 d . . . C11 C 0.27298(15) 0.09087(6) 0.5766(4) 0.0781(7) Uani 1 1 d . . . C12 C 0.5000 0.0000 0.4564(4) 0.0645(8) Uani 1 2 d S . . C13 C 0.50480(19) 0.03307(9) 0.3191(5) 0.0912(8) Uani 1 1 d . . . H2 H 0.4352(13) -0.0487(6) 0.783(4) 0.095(7) Uiso 1 1 d . . . H3 H 0.3121(13) -0.0252(5) 0.968(4) 0.082(7) Uiso 1 1 d . . . H5 H 0.2462(12) 0.0324(5) 0.976(4) 0.075(6) Uiso 1 1 d . . . H7 H 0.1786(17) 0.0876(7) 1.033(6) 0.128(11) Uiso 1 1 d . . . H8 H 0.1423(18) 0.1426(8) 0.917(6) 0.123(11) Uiso 1 1 d . . . H9 H 0.1800(16) 0.1639(8) 0.614(5) 0.115(10) Uiso 1 1 d . . . H10 H 0.2699(16) 0.1336(7) 0.377(6) 0.110(9) Uiso 1 1 d . . . H11 H 0.3050(12) 0.0771(6) 0.501(4) 0.073(7) Uiso 1 1 d . . . H13A H 0.5496(16) 0.0327(7) 0.231(5) 0.108(9) Uiso 1 1 d . . . H13B H 0.4479(18) 0.0331(7) 0.231(5) 0.127(11) Uiso 1 1 d . . . H13C H 0.5031(14) 0.0556(7) 0.414(5) 0.101(9) Uiso 1 1 d . . . N1 N 0.38299(9) 0.02872(4) 0.6159(3) 0.0598(4) Uani 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 0.0632(11) 0.0534(12) 0.0540(10) 0.0001(10) -0.0103(10) 0.0044(9) C2 0.0740(14) 0.0594(13) 0.0737(14) 0.0135(12) -0.0095(12) 0.0046(11) C3 0.0703(14) 0.0698(13) 0.0748(13) 0.0209(13) 0.0000(13) -0.0038(11) C4 0.0581(11) 0.0579(12) 0.0582(12) 0.0082(10) -0.0027(10) -0.0037(9) C5 0.0598(11) 0.0721(14) 0.0675(13) 0.0059(12) 0.0036(12) -0.0064(10) C6 0.0552(11) 0.0627(13) 0.0785(14) -0.0005(12) -0.0004(11) -0.0036(10) C7 0.0815(16) 0.0822(18) 0.111(2) 0.0028(18) 0.0234(16) 0.0039(14) C8 0.099(2) 0.081(2) 0.165(3) -0.010(2) 0.043(2) 0.0149(15) C9 0.0818(17) 0.0667(17) 0.162(3) 0.014(2) 0.010(2) 0.0090(14) C10 0.0944(19) 0.0697(16) 0.107(2) 0.0162(16) 0.0044(17) 0.0143(14) C11 0.0836(15) 0.0686(15) 0.0821(17) 0.0085(14) 0.0066(14) 0.0126(12) C12 0.078(2) 0.068(2) 0.0466(15) 0.000 0.000 0.0157(15) C13 0.101(2) 0.100(2) 0.0725(16) 0.0284(16) 0.0229(16) 0.0292(16) N1 0.0659(9) 0.0559(10) 0.0575(9) 0.0039(9) 0.0012(9) 0.0012(8) _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 N1 1.306(2) . ? C1 C2 1.456(3) . ? C1 C12 1.516(3) . ? C2 C3 1.331(3) . ? C3 C4 1.446(3) . ? C4 C5 1.350(3) . ? C4 N1 1.404(3) . ? C5 C6 1.453(3) . ? C6 C7 1.377(4) . ? C6 C11 1.388(3) . ? C7 C8 1.374(4) . ? C8 C9 1.375(5) . ? C9 C10 1.353(4) . ? C10 C11 1.363(3) . ? C12 C1 1.516(3) 2_655 ? C12 C13 1.525(3) 2_655 ? C12 C13 1.525(3) . ? 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 N1 C1 C2 111.79(18) . . ? N1 C1 C12 123.65(16) . . ? C2 C1 C12 124.50(16) . . ? C3 C2 C1 106.58(19) . . ? C2 C3 C4 106.7(2) . . ? C5 C4 N1 125.27(19) . . ? C5 C4 C3 125.6(2) . . ? N1 C4 C3 109.07(17) . . ? C4 C5 C6 130.2(2) . . ? C7 C6 C11 117.8(2) . . ? C7 C6 C5 118.6(2) . . ? C11 C6 C5 123.7(2) . . ? C8 C7 C6 121.0(3) . . ? C7 C8 C9 120.1(3) . . ? C10 C9 C8 119.1(3) . . ? C9 C10 C11 121.5(3) . . ? C10 C11 C6 120.5(3) . . ? C1 C12 C1 105.5(2) . 2_655 ? C1 C12 C13 109.36(16) . 2_655 ? C1 C12 C13 110.06(13) 2_655 2_655 ? C1 C12 C13 110.06(13) . . ? C1 C12 C13 109.36(16) 2_655 . ? C13 C12 C13 112.3(3) 2_655 . ? C1 N1 C4 105.83(15) . . ? _diffrn_measured_fraction_theta_max 0.946 _diffrn_reflns_theta_full 27.31 _diffrn_measured_fraction_theta_full 0.946 _refine_diff_density_max 0.093 _refine_diff_density_min -0.087 _refine_diff_density_rms 0.022 #===END