Supplementary Material (ESI) for Organic & Biomolecular Chemistry This journal is © The Royal Society of Chemistry 2003 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 loop_ _publ_author_name 'Francois Diederich' 'Corinne Boudon' 'Jean-Paul Gisselbrecht' 'Robin Gist' 'Maurice Gross' 'Masahiro Irie' ; T.Kawai ; 'Atsushi Kishioka' 'Paul Seiler' _publ_contact_author_name 'Prof Francois Diederich' _publ_contact_author_address ; Laboratorium fur Organische Chemie ETH Hoenggerberg ETH Hoengerberg, HCI Zuerich 8093 SWITZERLAND ; _publ_contact_author_email DIEDERICH@ORG.CHEM.ETHZ.CH _publ_section_title ; Donor-substituted cyanoethynylethenes: powerful chromophores for opto-electronic applications ; data_moon3_D_02 _database_code_CSD 207516 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety 'C15 H10 N4' _chemical_formula_sum 'C15 H10 N4' _chemical_formula_weight 246.27 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' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.014(1) _cell_length_b 7.085(1) _cell_length_c 14.149(2) _cell_angle_alpha 77.79(2) _cell_angle_beta 89.21(1) _cell_angle_gamma 77.40(2) _cell_volume 670.28(16) _cell_formula_units_Z 2 _cell_measurement_temperature 243(2) _cell_measurement_reflns_used 18 _cell_measurement_theta_min 18.80 _cell_measurement_theta_max 27.10 _exptl_crystal_description 'Cut fragment' _exptl_crystal_colour black _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.220 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 256 _exptl_absorpt_coefficient_mu 0.611 _exptl_absorpt_correction_type non _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 243(2) _diffrn_radiation_wavelength 1.5418 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'NONIUS CAD4' _diffrn_measurement_method \q/\q _diffrn_detector_area_resol_mean ? _diffrn_standards_number 2 _diffrn_standards_interval_count ? _diffrn_standards_interval_time '167 min.' _diffrn_standards_decay_% 0.800 _diffrn_reflns_number 2922 _diffrn_reflns_av_R_equivalents 0.008 _diffrn_reflns_av_sigmaI/netI 0.0159 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 3.20 _diffrn_reflns_theta_max 74.87 _reflns_number_total 2631 _reflns_number_gt 2304 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CAD4 VMS-software (Nonius, 1989)' _computing_cell_refinement 'CAD4 VMS-software (Nonius, 1989)' _computing_data_reduction 'MOLEN VMS-software (Nonius, 1990)' _computing_structure_solution 'SIR92 (Altomare et al.,1994)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP (Johnson,1976)' _computing_publication_material SHELXL97 _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 'w=1/[\s^2^(Fo^2^)+(0.0940P)^2^+0.1788P] 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 'H-atoms riding' _refine_ls_extinction_method SHELXL97 _refine_ls_extinction_coef 0.0026(13) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2631 _refine_ls_number_parameters 183 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0640 _refine_ls_R_factor_gt 0.0583 _refine_ls_wR_factor_ref 0.1787 _refine_ls_wR_factor_gt 0.1721 _refine_ls_goodness_of_fit_ref 1.090 _refine_ls_restrained_S_all 1.090 _refine_ls_shift/su_max 0.026 _refine_ls_shift/su_mean 0.004 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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.4159(2) 0.2533(2) -0.07767(10) 0.0421(4) Uani 1 d . . . C2 C 0.2214(3) 0.2811(3) -0.10724(11) 0.0469(4) Uani 1 d . . . H2A H 0.1225 0.3023 -0.0627 0.069(6) Uiso 1 calc R . . C3 C 0.1715(3) 0.2781(3) -0.19984(12) 0.0483(4) Uani 1 d . . . H3A H 0.0389 0.2986 -0.2180 0.063(6) Uiso 1 calc R . . C4 C 0.3161(3) 0.2448(2) -0.26880(10) 0.0458(4) Uani 1 d . . . C5 C 0.5125(3) 0.2174(3) -0.23812(12) 0.0501(4) Uani 1 d . . . H5A H 0.6122 0.1962 -0.2823 0.081(7) Uiso 1 calc R . . C6 C 0.5610(3) 0.2210(2) -0.14514(12) 0.0473(4) Uani 1 d . . . H6A H 0.6931 0.2016 -0.1264 0.054(5) Uiso 1 calc R . . N7 N 0.2667(3) 0.2356(2) -0.35977(10) 0.0630(5) Uani 1 d . . . C8 C 0.0648(4) 0.2685(4) -0.39125(16) 0.0839(8) Uani 1 d . . . H8A H 0.0586 0.2567 -0.4581 0.132(12) Uiso 1 calc R . . H8B H -0.0036 0.4001 -0.3857 0.107(10) Uiso 1 calc R . . H8C H 0.0039 0.1708 -0.3511 0.085(8) Uiso 1 calc R . . C9 C 0.4148(5) 0.2254(4) -0.43342(14) 0.0892(9) Uani 1 d . . . H9A H 0.3550 0.2202 -0.4940 0.122(11) Uiso 1 calc R . . H9B H 0.5173 0.1076 -0.4126 0.112(10) Uiso 1 calc R . . H9C H 0.4703 0.3418 -0.4425 0.122(12) Uiso 1 calc R . . C10 C 0.4650(3) 0.2590(2) 0.01784(11) 0.0466(4) Uani 1 d . . . C11 C 0.5046(3) 0.2646(2) 0.09996(11) 0.0490(4) Uani 1 d . . . C12 C 0.5438(3) 0.2693(2) 0.19568(11) 0.0460(4) Uani 1 d . . . C13 C 0.3827(3) 0.2997(3) 0.25918(12) 0.0501(4) Uani 1 d . . . N14 N 0.2544(3) 0.3204(3) 0.30835(14) 0.0790(6) Uani 1 d . . . C15 C 0.7278(3) 0.2456(2) 0.23338(11) 0.0474(4) Uani 1 d . . . C16 C 0.7574(3) 0.2535(3) 0.33228(12) 0.0504(4) Uani 1 d . . . N17 N 0.7836(3) 0.2588(3) 0.41084(11) 0.0679(5) Uani 1 d . . . C18 C 0.8924(3) 0.2069(3) 0.17396(13) 0.0525(4) Uani 1 d . . . N19 N 1.0240(3) 0.1745(4) 0.12828(16) 0.0859(6) Uani 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 0.0617(9) 0.0370(8) 0.0286(7) -0.0071(5) -0.0021(6) -0.0126(6) C2 0.0580(9) 0.0502(9) 0.0337(7) -0.0107(6) 0.0056(6) -0.0132(7) C3 0.0557(9) 0.0511(9) 0.0383(8) -0.0102(7) -0.0040(7) -0.0117(7) C4 0.0727(11) 0.0358(8) 0.0286(7) -0.0075(6) -0.0016(6) -0.0106(7) C5 0.0662(10) 0.0467(9) 0.0389(8) -0.0139(7) 0.0115(7) -0.0116(8) C6 0.0540(9) 0.0441(9) 0.0445(8) -0.0111(7) 0.0003(7) -0.0106(7) N7 0.1021(13) 0.0559(9) 0.0299(7) -0.0132(6) -0.0077(7) -0.0101(8) C8 0.124(2) 0.0732(15) 0.0513(11) -0.0189(10) -0.0400(12) -0.0059(14) C9 0.149(2) 0.0824(16) 0.0310(9) -0.0190(9) 0.0132(11) -0.0084(17) C10 0.0659(10) 0.0412(9) 0.0340(8) -0.0064(6) -0.0040(7) -0.0156(7) C11 0.0675(11) 0.0445(9) 0.0368(8) -0.0079(6) -0.0030(7) -0.0166(8) C12 0.0604(10) 0.0426(8) 0.0356(8) -0.0084(6) 0.0017(6) -0.0124(7) C13 0.0537(9) 0.0584(10) 0.0397(8) -0.0137(7) 0.0000(7) -0.0121(8) N14 0.0638(10) 0.1094(16) 0.0653(11) -0.0264(10) 0.0165(9) -0.0157(10) C15 0.0596(10) 0.0447(9) 0.0386(8) -0.0099(6) 0.0000(7) -0.0118(7) C16 0.0583(10) 0.0522(10) 0.0415(9) -0.0117(7) -0.0057(7) -0.0119(8) N17 0.0790(11) 0.0895(13) 0.0396(8) -0.0206(8) -0.0083(7) -0.0203(9) C18 0.0529(9) 0.0578(10) 0.0500(9) -0.0180(8) 0.0046(7) -0.0132(8) N19 0.0700(12) 0.1017(15) 0.0948(15) -0.0397(12) 0.0283(11) -0.0213(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 C2 1.392(2) . ? C1 C6 1.401(2) . ? C1 C10 1.410(2) . ? C2 C3 1.366(2) . ? C3 C4 1.415(2) . ? C4 N7 1.356(2) . ? C4 C5 1.410(3) . ? C5 C6 1.370(2) . ? N7 C8 1.445(3) . ? N7 C9 1.463(3) . ? C10 C11 1.209(2) . ? C11 C12 1.394(2) . ? C12 C15 1.365(3) . ? C12 C13 1.442(2) . ? C13 N14 1.133(2) . ? C15 C18 1.431(2) . ? C15 C16 1.432(2) . ? C16 N17 1.139(2) . ? C18 N19 1.129(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 C2 C1 C6 118.46(15) . . ? C2 C1 C10 120.59(15) . . ? C6 C1 C10 120.95(15) . . ? C3 C2 C1 121.24(15) . . ? C2 C3 C4 121.06(16) . . ? N7 C4 C5 121.82(17) . . ? N7 C4 C3 120.97(17) . . ? C5 C4 C3 117.20(14) . . ? C6 C5 C4 121.27(16) . . ? C5 C6 C1 120.77(16) . . ? C4 N7 C8 121.42(19) . . ? C4 N7 C9 120.2(2) . . ? C8 N7 C9 117.60(18) . . ? C11 C10 C1 179.17(18) . . ? C10 C11 C12 177.93(19) . . ? C15 C12 C11 123.57(16) . . ? C15 C12 C13 117.64(15) . . ? C11 C12 C13 118.79(16) . . ? N14 C13 C12 178.4(2) . . ? C12 C15 C18 119.45(15) . . ? C12 C15 C16 120.63(16) . . ? C18 C15 C16 119.90(16) . . ? N17 C16 C15 179.1(2) . . ? N19 C18 C15 178.9(2) . . ? 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 C2 C3 -0.3(3) . . . . ? C10 C1 C2 C3 179.28(15) . . . . ? C1 C2 C3 C4 0.6(3) . . . . ? C2 C3 C4 N7 177.87(15) . . . . ? C2 C3 C4 C5 -0.8(2) . . . . ? N7 C4 C5 C6 -177.98(15) . . . . ? C3 C4 C5 C6 0.6(2) . . . . ? C4 C5 C6 C1 -0.4(3) . . . . ? C2 C1 C6 C5 0.2(2) . . . . ? C10 C1 C6 C5 -179.41(14) . . . . ? C5 C4 N7 C8 -178.51(18) . . . . ? C3 C4 N7 C8 2.9(3) . . . . ? C5 C4 N7 C9 -9.0(3) . . . . ? C3 C4 N7 C9 172.46(18) . . . . ? C2 C1 C10 C11 -6(11) . . . . ? C6 C1 C10 C11 173(100) . . . . ? C1 C10 C11 C12 29(15) . . . . ? C10 C11 C12 C15 158(5) . . . . ? C10 C11 C12 C13 -21(5) . . . . ? C15 C12 C13 N14 -133(7) . . . . ? C11 C12 C13 N14 47(7) . . . . ? C11 C12 C15 C18 -2.2(3) . . . . ? C13 C12 C15 C18 177.41(15) . . . . ? C11 C12 C15 C16 179.60(15) . . . . ? C13 C12 C15 C16 -0.8(3) . . . . ? C12 C15 C16 N17 170(12) . . . . ? C18 C15 C16 N17 -8(12) . . . . ? C12 C15 C18 N19 -145(11) . . . . ? C16 C15 C18 N19 33(12) . . . . ? _diffrn_measured_fraction_theta_max 0.956 _diffrn_reflns_theta_full 74.87 _diffrn_measured_fraction_theta_full 0.956 _refine_diff_density_max 0.648 _refine_diff_density_min -0.221 _refine_diff_density_rms 0.041 data_moon4_D_02 _database_code_CSD 207517 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety 'C24 H20 N4' _chemical_formula_sum 'C24 H20 N4' _chemical_formula_weight 364.44 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 Monoclinic _symmetry_space_group_name_H-M P2(1)/n 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 3.9477(2) _cell_length_b 11.1064(4) _cell_length_c 22.3725(9) _cell_angle_alpha 90.00 _cell_angle_beta 93.769(2) _cell_angle_gamma 90.00 _cell_volume 978.79(7) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 1778 _cell_measurement_theta_min 2.05 _cell_measurement_theta_max 27.52 _exptl_crystal_description 'Cut fragment' _exptl_crystal_colour black _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.237 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 384 _exptl_absorpt_coefficient_mu 0.075 _exptl_absorpt_correction_type non _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Kappa CCD' _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_reflns_number 4186 _diffrn_reflns_av_R_equivalents 0.0476 _diffrn_reflns_av_sigmaI/netI 0.0702 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 2.05 _diffrn_reflns_theta_max 27.52 _reflns_number_total 2232 _reflns_number_gt 1350 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Kappa CCD' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'Denzo + Scalepak (Otwinowski & Minor, 1997)' _computing_structure_solution 'SIR92 (Altomare et al.,1994)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP (Johnson,1976)' _computing_publication_material SHELXL97 _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 'w=1/[\s^2^(Fo^2^)+(0.0585P)^2^+0.0806P] 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 'H-atoms riding' _refine_ls_extinction_method SHELXL97 _refine_ls_extinction_coef 0.061(10) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2232 _refine_ls_number_parameters 128 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1077 _refine_ls_R_factor_gt 0.0531 _refine_ls_wR_factor_ref 0.1582 _refine_ls_wR_factor_gt 0.1081 _refine_ls_goodness_of_fit_ref 1.267 _refine_ls_restrained_S_all 1.267 _refine_ls_shift/su_max 0.106 _refine_ls_shift/su_mean 0.008 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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C -0.9970(5) -0.04818(19) -0.98078(8) 0.0285(5) Uani 1 d . . . C2 C -1.1246(5) -0.1621(2) -1.00341(9) 0.0335(5) Uani 1 d . . . N3 N -1.2263(5) -0.2524(2) -1.02167(9) 0.0496(6) Uani 1 d . . . C4 C -0.8674(5) -0.04151(19) -0.92028(9) 0.0298(5) Uani 1 d . . . C5 C -0.7538(5) -0.02860(19) -0.86928(9) 0.0288(5) Uani 1 d . . . C6 C -0.6189(5) -0.00817(19) -0.80964(8) 0.0269(5) Uani 1 d . . . C7 C -0.4373(5) 0.09687(19) -0.79510(9) 0.0273(5) Uani 1 d . . . H7A H -0.4012 0.1533 -0.8253 0.025 Uiso 1 d R . . C8 C -0.3107(5) 0.11914(19) -0.73769(9) 0.0264(5) Uani 1 d . . . H8A H -0.1906 0.1909 -0.7293 0.023 Uiso 1 d R . . C9 C -0.3572(5) 0.03669(18) -0.69099(8) 0.0256(5) Uani 1 d . . . C10 C -0.5412(5) -0.06934(19) -0.70576(9) 0.0268(5) Uani 1 d . . . H10A H -0.5768 -0.1264 -0.6758 0.032 Uiso 1 d R . . C11 C -0.6692(5) -0.09016(19) -0.76344(9) 0.0274(5) Uani 1 d . . . H11A H -0.7931 -0.1610 -0.7721 0.026 Uiso 1 d R . . N12 N -0.2292(4) 0.05905(17) -0.63378(7) 0.0303(5) Uani 1 d . . . C13 C -0.0507(5) 0.1709(2) -0.61991(9) 0.0328(5) Uani 1 d . . . H13A H 0.0252 0.1721 -0.5778 0.039 Uiso 1 d R . . H13B H -0.2023 0.2383 -0.6287 0.036 Uiso 1 d R . . H13C H 0.1441 0.1772 -0.6440 0.036 Uiso 1 d R . . C14 C -0.3042(6) -0.0213(2) -0.58504(9) 0.0377(6) Uani 1 d . . . H14A H -0.1926 0.0079 -0.5479 0.058 Uiso 1 d R . . H14B H -0.2222 -0.1015 -0.5934 0.062 Uiso 1 d R . . H14C H -0.5475 -0.0239 -0.5813 0.045 Uiso 1 d 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 0.0248(10) 0.0313(12) 0.0291(12) -0.0045(9) 0.0003(9) -0.0002(9) C2 0.0359(12) 0.0363(14) 0.0282(12) 0.0000(10) 0.0018(9) -0.0021(11) N3 0.0617(14) 0.0394(13) 0.0477(13) -0.0070(10) 0.0035(10) -0.0106(10) C4 0.0277(11) 0.0298(12) 0.0322(13) -0.0023(9) 0.0032(9) -0.0012(9) C5 0.0251(11) 0.0286(12) 0.0328(12) -0.0005(9) 0.0037(9) 0.0008(9) C6 0.0235(10) 0.0307(12) 0.0264(11) -0.0025(9) 0.0018(8) 0.0045(9) C7 0.0255(11) 0.0268(12) 0.0298(12) 0.0036(9) 0.0039(9) 0.0028(9) C8 0.0235(11) 0.0233(11) 0.0324(12) -0.0029(9) 0.0013(8) -0.0004(8) C9 0.0208(10) 0.0274(12) 0.0286(11) -0.0027(9) 0.0021(8) 0.0050(8) C10 0.0258(10) 0.0254(12) 0.0295(12) 0.0030(9) 0.0033(8) 0.0023(9) C11 0.0225(10) 0.0250(12) 0.0350(12) -0.0035(9) 0.0023(8) 0.0010(9) N12 0.0301(10) 0.0338(11) 0.0265(10) -0.0010(8) -0.0016(7) -0.0014(8) C13 0.0278(11) 0.0369(13) 0.0333(12) -0.0056(10) -0.0019(9) 0.0018(10) C14 0.0382(12) 0.0420(15) 0.0324(12) 0.0034(11) -0.0013(9) 0.0007(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 C1 1.372(4) 3_353 ? C1 C4 1.417(3) . ? C1 C2 1.441(3) . ? C2 N3 1.146(3) . ? C4 C5 1.207(3) . ? C5 C6 1.422(3) . ? C6 C7 1.397(3) . ? C6 C11 1.401(3) . ? C7 C8 1.370(3) . ? C8 C9 1.410(3) . ? C9 N12 1.368(2) . ? C9 C10 1.411(3) . ? C10 C11 1.374(3) . ? N12 C13 1.452(3) . ? N12 C14 1.454(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 C1 C1 C4 123.2(2) 3_353 . ? C1 C1 C2 118.3(2) 3_353 . ? C4 C1 C2 118.51(18) . . ? N3 C2 C1 179.7(2) . . ? C5 C4 C1 176.1(2) . . ? C4 C5 C6 177.6(2) . . ? C7 C6 C11 117.81(18) . . ? C7 C6 C5 120.45(18) . . ? C11 C6 C5 121.73(19) . . ? C8 C7 C6 121.29(19) . . ? C7 C8 C9 121.34(19) . . ? N12 C9 C8 121.15(18) . . ? N12 C9 C10 121.57(18) . . ? C8 C9 C10 117.28(17) . . ? C11 C10 C9 120.80(19) . . ? C10 C11 C6 121.47(18) . . ? C9 N12 C13 119.98(17) . . ? C9 N12 C14 120.62(18) . . ? C13 N12 C14 118.99(16) . . ? 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 C1 C1 C2 N3 5(42) 3_353 . . . ? C4 C1 C2 N3 -174(100) . . . . ? C1 C1 C4 C5 3(3) 3_353 . . . ? C2 C1 C4 C5 -178(100) . . . . ? C1 C4 C5 C6 4(8) . . . . ? C4 C5 C6 C7 -20(5) . . . . ? C4 C5 C6 C11 158(5) . . . . ? C11 C6 C7 C8 0.3(3) . . . . ? C5 C6 C7 C8 178.82(18) . . . . ? C6 C7 C8 C9 0.3(3) . . . . ? C7 C8 C9 N12 179.73(18) . . . . ? C7 C8 C9 C10 -0.4(3) . . . . ? N12 C9 C10 C11 179.76(18) . . . . ? C8 C9 C10 C11 -0.1(3) . . . . ? C9 C10 C11 C6 0.7(3) . . . . ? C7 C6 C11 C10 -0.8(3) . . . . ? C5 C6 C11 C10 -179.31(18) . . . . ? C8 C9 N12 C13 1.9(3) . . . . ? C10 C9 N12 C13 -178.00(17) . . . . ? C8 C9 N12 C14 174.51(18) . . . . ? C10 C9 N12 C14 -5.4(3) . . . . ? _diffrn_measured_fraction_theta_max 0.941 _diffrn_reflns_theta_full 27.52 _diffrn_measured_fraction_theta_full 0.941 _refine_diff_density_max 0.316 _refine_diff_density_min -0.299 _refine_diff_density_rms 0.092