# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # 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_dyj-12 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C28 H20 N2' _chemical_formula_weight 384.46 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 triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.850(7) _cell_length_b 9.230(12) _cell_length_c 9.341(10) _cell_angle_alpha 65.88(4) _cell_angle_beta 69.95(4) _cell_angle_gamma 77.39(5) _cell_volume 504.2(10) _cell_formula_units_Z 1 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.58 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.266 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 202 _exptl_absorpt_coefficient_mu 0.074 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9579 _exptl_absorpt_correction_T_max 0.9836 _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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4939 _diffrn_reflns_av_R_equivalents 0.0219 _diffrn_reflns_av_sigmaI/netI 0.0315 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 3.18 _diffrn_reflns_theta_max 27.48 _reflns_number_total 2274 _reflns_number_gt 1529 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.1159P)^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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2274 _refine_ls_number_parameters 136 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0726 _refine_ls_R_factor_gt 0.0463 _refine_ls_wR_factor_ref 0.1889 _refine_ls_wR_factor_gt 0.1496 _refine_ls_goodness_of_fit_ref 1.077 _refine_ls_restrained_S_all 1.077 _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 0.3008(3) 0.7197(2) 0.2621(2) 0.0473(4) Uani 1 1 d . . . H1 H 0.2124 0.6852 0.2282 0.057 Uiso 1 1 calc R . . C2 C 0.3297(3) 0.8770(2) 0.1990(2) 0.0569(5) Uani 1 1 d . . . H2 H 0.2599 0.9486 0.1245 0.068 Uiso 1 1 calc R . . C3 C 0.4657(3) 0.9322(2) 0.2463(2) 0.0593(5) Uani 1 1 d . . . H3 H 0.4885 1.0396 0.2000 0.071 Uiso 1 1 calc R . . C4 C 0.5628(3) 0.8295(2) 0.3585(2) 0.0504(5) Uani 1 1 d . . . H4 H 0.6495 0.8683 0.3899 0.061 Uiso 1 1 calc R . . C5 C 0.5355(2) 0.66293(19) 0.43014(18) 0.0385(4) Uani 1 1 d . . . C6 C 0.4018(2) 0.60544(19) 0.37894(18) 0.0378(4) Uani 1 1 d . . . C7 C 0.3690(2) 0.44249(19) 0.44836(18) 0.0376(4) Uani 1 1 d . . . C8 C 0.2325(2) 0.3790(2) 0.3978(2) 0.0425(4) Uani 1 1 d . . . H8 H 0.1120 0.3373 0.4769 0.051 Uiso 1 1 calc R . . C9 C 0.2664(3) 0.3765(2) 0.2519(2) 0.0470(5) Uani 1 1 d . . . H9 H 0.3887 0.4165 0.1740 0.056 Uiso 1 1 calc R . . C10 C 0.1319(2) 0.3173(2) 0.1982(2) 0.0421(4) Uani 1 1 d . . . C11 C -0.0525(3) 0.2500(2) 0.3008(2) 0.0546(5) Uani 1 1 d . . . H11 H -0.0942 0.2357 0.4111 0.066 Uiso 1 1 calc R . . C12 C -0.1732(3) 0.2044(3) 0.2374(3) 0.0636(6) Uani 1 1 d . . . H12 H -0.2973 0.1614 0.3082 0.076 Uiso 1 1 calc R . . C13 C 0.0538(3) 0.2783(3) -0.0135(3) 0.0622(6) Uani 1 1 d . . . H13 H 0.0937 0.2875 -0.1224 0.075 Uiso 1 1 calc R . . C14 C 0.1845(3) 0.3289(2) 0.0369(2) 0.0514(5) Uani 1 1 d . . . H14 H 0.3079 0.3708 -0.0370 0.062 Uiso 1 1 calc R . . N1 N -0.1253(3) 0.2175(2) 0.0825(2) 0.0664(5) 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 0.0514(9) 0.0501(10) 0.0470(9) -0.0173(8) -0.0242(7) -0.0018(7) C2 0.0688(12) 0.0476(11) 0.0558(11) -0.0108(8) -0.0327(9) 0.0003(9) C3 0.0749(13) 0.0401(10) 0.0644(12) -0.0099(8) -0.0309(10) -0.0085(9) C4 0.0577(10) 0.0443(10) 0.0553(10) -0.0155(8) -0.0221(8) -0.0118(8) C5 0.0386(8) 0.0416(9) 0.0394(8) -0.0166(7) -0.0117(6) -0.0066(6) C6 0.0362(7) 0.0425(9) 0.0383(8) -0.0165(7) -0.0133(6) -0.0028(6) C7 0.0360(8) 0.0454(9) 0.0386(8) -0.0197(7) -0.0125(6) -0.0058(7) C8 0.0393(8) 0.0480(9) 0.0471(9) -0.0190(7) -0.0152(7) -0.0092(7) C9 0.0415(8) 0.0591(11) 0.0479(9) -0.0236(8) -0.0113(7) -0.0132(8) C10 0.0417(8) 0.0437(9) 0.0497(9) -0.0225(7) -0.0179(7) -0.0019(7) C11 0.0500(10) 0.0716(13) 0.0570(10) -0.0346(10) -0.0149(8) -0.0127(9) C12 0.0526(10) 0.0806(14) 0.0772(13) -0.0417(11) -0.0188(9) -0.0175(10) C13 0.0679(12) 0.0784(14) 0.0620(11) -0.0410(10) -0.0336(10) 0.0065(10) C14 0.0498(9) 0.0606(12) 0.0511(10) -0.0257(8) -0.0166(8) -0.0048(8) N1 0.0649(10) 0.0824(13) 0.0795(12) -0.0464(10) -0.0332(9) -0.0063(9) _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 1.356(3) . ? C1 C6 1.429(3) . ? C1 H1 0.9300 . ? C2 C3 1.412(3) . ? C2 H2 0.9300 . ? C3 C4 1.353(3) . ? C3 H3 0.9300 . ? C4 C5 1.431(3) . ? C4 H4 0.9300 . ? C5 C7 1.411(3) 2_666 ? C5 C6 1.438(2) . ? C6 C7 1.408(3) . ? C7 C5 1.411(3) 2_666 ? C7 C8 1.486(2) . ? C8 C9 1.311(3) . ? C8 H8 0.9300 . ? C9 C10 1.470(2) . ? C9 H9 0.9300 . ? C10 C14 1.387(3) . ? C10 C11 1.388(3) . ? C11 C12 1.380(3) . ? C11 H11 0.9300 . ? C12 N1 1.328(3) . ? C12 H12 0.9300 . ? C13 N1 1.327(3) . ? C13 C14 1.375(3) . ? C13 H13 0.9300 . ? C14 H14 0.9300 . ? 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 122.02(17) . . ? C2 C1 H1 119.0 . . ? C6 C1 H1 119.0 . . ? C1 C2 C3 120.16(19) . . ? C1 C2 H2 119.9 . . ? C3 C2 H2 119.9 . . ? C4 C3 C2 120.28(19) . . ? C4 C3 H3 119.9 . . ? C2 C3 H3 119.9 . . ? C3 C4 C5 121.68(17) . . ? C3 C4 H4 119.2 . . ? C5 C4 H4 119.2 . . ? C7 C5 C4 121.37(15) 2_666 . ? C7 C5 C6 120.38(16) 2_666 . ? C4 C5 C6 118.22(16) . . ? C7 C6 C1 122.55(15) . . ? C7 C6 C5 119.82(15) . . ? C1 C6 C5 117.60(17) . . ? C6 C7 C5 119.80(14) . 2_666 ? C6 C7 C8 121.20(16) . . ? C5 C7 C8 118.99(16) 2_666 . ? C9 C8 C7 126.01(15) . . ? C9 C8 H8 117.0 . . ? C7 C8 H8 117.0 . . ? C8 C9 C10 126.99(16) . . ? C8 C9 H9 116.5 . . ? C10 C9 H9 116.5 . . ? C14 C10 C11 116.17(15) . . ? C14 C10 C9 120.33(16) . . ? C11 C10 C9 123.49(17) . . ? C12 C11 C10 119.27(19) . . ? C12 C11 H11 120.4 . . ? C10 C11 H11 120.4 . . ? N1 C12 C11 124.83(19) . . ? N1 C12 H12 117.6 . . ? C11 C12 H12 117.6 . . ? N1 C13 C14 124.4(2) . . ? N1 C13 H13 117.8 . . ? C14 C13 H13 117.8 . . ? C13 C14 C10 119.89(18) . . ? C13 C14 H14 120.1 . . ? C10 C14 H14 120.1 . . ? C13 N1 C12 115.37(16) . . ? _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.228 _refine_diff_density_min -0.200 _refine_diff_density_rms 0.053 _database_code_depnum_ccdc_archive 'CCDC 943524' ####################################################################### # # 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_dyj-9 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C28 H20 N2' _chemical_formula_weight 384.46 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 P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 7.5957(15) _cell_length_b 5.7108(11) _cell_length_c 22.899(5) _cell_angle_alpha 90.00 _cell_angle_beta 95.95(3) _cell_angle_gamma 90.00 _cell_volume 987.9(3) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.09 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.292 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 404 _exptl_absorpt_coefficient_mu 0.076 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9910 _exptl_absorpt_correction_T_max 0.9940 _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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9226 _diffrn_reflns_av_R_equivalents 0.0213 _diffrn_reflns_av_sigmaI/netI 0.0182 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 3.08 _diffrn_reflns_theta_max 27.48 _reflns_number_total 2253 _reflns_number_gt 1634 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0720P)^2^+0.1187P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2253 _refine_ls_number_parameters 136 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0596 _refine_ls_R_factor_gt 0.0428 _refine_ls_wR_factor_ref 0.1380 _refine_ls_wR_factor_gt 0.1269 _refine_ls_goodness_of_fit_ref 1.081 _refine_ls_restrained_S_all 1.081 _refine_ls_shift/su_max 0.019 _refine_ls_shift/su_mean 0.003 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 0.19653(18) 1.0169(3) 0.29395(7) 0.0477(4) Uani 1 1 d . . . H1 H 0.1171 1.1412 0.2928 0.057 Uiso 1 1 calc R . . C2 C 0.34156(18) 1.0222(2) 0.33582(6) 0.0426(3) Uani 1 1 d . . . H2 H 0.3564 1.1459 0.3623 0.051 Uiso 1 1 calc R . . C3 C 0.46462(16) 0.8424(2) 0.33811(5) 0.0350(3) Uani 1 1 d . . . C4 C 0.43031(18) 0.6624(2) 0.29820(6) 0.0430(3) Uani 1 1 d . . . H4 H 0.5079 0.5365 0.2979 0.052 Uiso 1 1 calc R . . C5 C 0.2799(2) 0.6707(3) 0.25861(6) 0.0494(4) Uani 1 1 d . . . H5 H 0.2589 0.5460 0.2327 0.059 Uiso 1 1 calc R . . C6 C 0.62647(17) 0.8367(2) 0.37986(6) 0.0415(3) Uani 1 1 d . . . H6 H 0.6974 0.7043 0.3788 0.050 Uiso 1 1 calc R . . C7 C 0.68034(17) 0.9966(3) 0.41780(6) 0.0430(4) Uani 1 1 d . . . H7 H 0.6086 1.1279 0.4193 0.052 Uiso 1 1 calc R . . C8 C 0.84523(16) 0.9921(2) 0.45930(5) 0.0359(3) Uani 1 1 d . . . C9 C 0.86652(16) 0.8297(2) 0.50593(5) 0.0355(3) Uani 1 1 d . . . C10 C 1.02341(16) 0.8396(2) 0.54712(5) 0.0351(3) Uani 1 1 d . . . C11 C 1.03913(18) 0.6759(3) 0.59457(6) 0.0425(3) Uani 1 1 d . . . H11 H 1.1369 0.6845 0.6225 0.051 Uiso 1 1 calc R . . C12 C 0.91570(19) 0.5088(3) 0.59993(6) 0.0480(4) Uani 1 1 d . . . H12 H 0.9309 0.4019 0.6307 0.058 Uiso 1 1 calc R . . C13 C 0.76350(19) 0.4962(3) 0.55886(6) 0.0503(4) Uani 1 1 d . . . H13 H 0.6799 0.3795 0.5624 0.060 Uiso 1 1 calc R . . C14 C 0.73863(18) 0.6531(3) 0.51437(6) 0.0456(4) Uani 1 1 d . . . H14 H 0.6356 0.6455 0.4887 0.055 Uiso 1 1 calc R . . N1 N 0.16375(15) 0.8445(2) 0.25514(5) 0.0496(3) 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 0.0356(7) 0.0529(9) 0.0514(8) -0.0014(7) -0.0113(6) 0.0058(6) C2 0.0385(7) 0.0440(8) 0.0422(7) -0.0083(6) -0.0104(6) 0.0026(6) C3 0.0294(6) 0.0425(7) 0.0313(6) 0.0024(5) -0.0055(5) -0.0010(5) C4 0.0410(7) 0.0437(8) 0.0431(7) -0.0054(6) -0.0020(6) 0.0029(6) C5 0.0503(8) 0.0535(9) 0.0418(7) -0.0124(7) -0.0072(6) -0.0079(7) C6 0.0346(7) 0.0471(8) 0.0400(7) -0.0026(6) -0.0102(5) 0.0081(6) C7 0.0327(7) 0.0521(8) 0.0412(7) -0.0024(6) -0.0107(5) 0.0051(6) C8 0.0290(6) 0.0463(7) 0.0304(6) -0.0045(6) -0.0074(5) 0.0025(5) C9 0.0298(6) 0.0456(7) 0.0296(6) -0.0045(5) -0.0033(5) 0.0011(5) C10 0.0308(6) 0.0436(7) 0.0295(6) -0.0037(5) -0.0036(5) 0.0051(5) C11 0.0395(7) 0.0517(8) 0.0343(6) 0.0024(6) -0.0047(5) 0.0076(6) C12 0.0500(9) 0.0532(9) 0.0404(7) 0.0101(6) 0.0029(6) 0.0050(7) C13 0.0457(8) 0.0594(9) 0.0457(8) 0.0032(7) 0.0042(6) -0.0108(7) C14 0.0352(7) 0.0626(9) 0.0376(7) -0.0003(7) -0.0033(5) -0.0068(6) N1 0.0389(6) 0.0615(8) 0.0447(7) -0.0043(6) -0.0141(5) -0.0047(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 1.3321(19) . ? C1 C2 1.3836(18) . ? C1 H1 0.9300 . ? C2 C3 1.3860(18) . ? C2 H2 0.9300 . ? C3 C4 1.3821(18) . ? C3 C6 1.4773(16) . ? C4 C5 1.3837(19) . ? C4 H4 0.9300 . ? C5 N1 1.3248(19) . ? C5 H5 0.9300 . ? C6 C7 1.2968(19) . ? C6 H6 0.9300 . ? C7 C8 1.4919(16) . ? C7 H7 0.9300 . ? C8 C10 1.4040(18) 3_776 ? C8 C9 1.4107(18) . ? C9 C14 1.4273(19) . ? C9 C10 1.4422(16) . ? C10 C8 1.4040(18) 3_776 ? C10 C11 1.4290(18) . ? C11 C12 1.352(2) . ? C11 H11 0.9300 . ? C12 C13 1.414(2) . ? C12 H12 0.9300 . ? C13 C14 1.355(2) . ? C13 H13 0.9300 . ? C14 H14 0.9300 . ? 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 123.97(13) . . ? N1 C1 H1 118.0 . . ? C2 C1 H1 118.0 . . ? C1 C2 C3 119.69(12) . . ? C1 C2 H2 120.2 . . ? C3 C2 H2 120.2 . . ? C4 C3 C2 116.47(11) . . ? C4 C3 C6 119.93(11) . . ? C2 C3 C6 123.59(11) . . ? C3 C4 C5 119.60(12) . . ? C3 C4 H4 120.2 . . ? C5 C4 H4 120.2 . . ? N1 C5 C4 124.37(13) . . ? N1 C5 H5 117.8 . . ? C4 C5 H5 117.8 . . ? C7 C6 C3 127.00(12) . . ? C7 C6 H6 116.5 . . ? C3 C6 H6 116.5 . . ? C6 C7 C8 126.90(13) . . ? C6 C7 H7 116.5 . . ? C8 C7 H7 116.5 . . ? C10 C8 C9 120.15(11) 3_776 . ? C10 C8 C7 118.70(12) 3_776 . ? C9 C8 C7 121.07(12) . . ? C8 C9 C14 122.74(11) . . ? C8 C9 C10 119.42(11) . . ? C14 C9 C10 117.83(11) . . ? C8 C10 C11 121.55(11) 3_776 . ? C8 C10 C9 120.42(11) 3_776 . ? C11 C10 C9 118.02(12) . . ? C12 C11 C10 121.79(12) . . ? C12 C11 H11 119.1 . . ? C10 C11 H11 119.1 . . ? C11 C12 C13 120.13(13) . . ? C11 C12 H12 119.9 . . ? C13 C12 H12 119.9 . . ? C14 C13 C12 120.46(13) . . ? C14 C13 H13 119.8 . . ? C12 C13 H13 119.8 . . ? C13 C14 C9 121.69(12) . . ? C13 C14 H14 119.2 . . ? C9 C14 H14 119.2 . . ? C5 N1 C1 115.87(11) . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.227 _refine_diff_density_min -0.158 _refine_diff_density_rms 0.033 _database_code_depnum_ccdc_archive 'CCDC 943525'