# Electronic Supplementary Material (ESI) for Chemical Communications # 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_shelxl _database_code_depnum_ccdc_archive 'CCDC 919148' #TrackingRef 'CCDC919148_revised.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C28 H22 N2, Cl2' _chemical_formula_sum 'C28 H22 Cl2 N2' _chemical_formula_weight 457.38 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' Cl Cl 0.1484 0.1585 '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 4.9933(10) _cell_length_b 7.9912(16) _cell_length_c 14.017(3) _cell_angle_alpha 87.95(3) _cell_angle_beta 85.51(3) _cell_angle_gamma 81.56(3) _cell_volume 551.40(19) _cell_formula_units_Z 1 _cell_measurement_temperature 291(2) _cell_measurement_reflns_used 4698 _cell_measurement_theta_min 3.85 _cell_measurement_theta_max 27.53 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.17 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.377 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 238 _exptl_absorpt_coefficient_mu 0.314 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8994 _exptl_absorpt_correction_T_max 0.9486 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 291(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 'Rigaku RAXIS-RAPID' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5455 _diffrn_reflns_av_R_equivalents 0.0250 _diffrn_reflns_av_unetI/netI 0.0334 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 3.85 _diffrn_reflns_theta_max 27.46 _reflns_number_total 2504 _reflns_number_gt 1959 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'RAPID-AUTO (Rigaku Corporation, 1998)' _computing_cell_refinement RAPID-AUTO _computing_data_reduction 'CrystalStructure (Rigaku/MSC and Rigaku Corporation, 2002)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material SHELXL-97 _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^)+(0.0675P)^2^+0.0882P] 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 2504 _refine_ls_number_parameters 145 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0549 _refine_ls_R_factor_gt 0.0427 _refine_ls_wR_factor_ref 0.1290 _refine_ls_wR_factor_gt 0.1152 _refine_ls_goodness_of_fit_ref 1.127 _refine_ls_restrained_S_all 1.127 _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 Cl1 Cl 1.39854(12) -0.22716(7) 0.09812(4) 0.0549(2) Uani 1 1 d . . . C1 C 0.2870(4) 0.2804(2) 0.51053(13) 0.0380(4) Uani 1 1 d . . . H1 H 0.4204 0.3004 0.4631 0.046 Uiso 1 1 calc R . . C2 C 0.2368(4) 0.3835(3) 0.58669(15) 0.0444(5) Uani 1 1 d . . . H2 H 0.3346 0.4732 0.5906 0.053 Uiso 1 1 calc R . . C3 C 0.0364(4) 0.3551(2) 0.66019(14) 0.0422(5) Uani 1 1 d . . . H3 H 0.0007 0.4275 0.7116 0.051 Uiso 1 1 calc R . . C4 C -0.1030(4) 0.2235(2) 0.65603(13) 0.0355(4) Uani 1 1 d . . . H4 H -0.2318 0.2055 0.7055 0.043 Uiso 1 1 calc R . . C5 C -0.0576(3) 0.1109(2) 0.57734(11) 0.0290(4) Uani 1 1 d . . . C6 C 0.1405(3) 0.1423(2) 0.50127(12) 0.0289(4) Uani 1 1 d . . . C7 C 0.1945(3) 0.0308(2) 0.42362(12) 0.0289(4) Uani 1 1 d . . . C8 C 0.4023(3) 0.0530(2) 0.34482(12) 0.0322(4) Uani 1 1 d . . . H8 H 0.5330 -0.0402 0.3313 0.039 Uiso 1 1 calc R . . C9 C 0.4223(4) 0.1909(2) 0.29173(12) 0.0338(4) Uani 1 1 d . . . H9 H 0.2885 0.2835 0.3028 0.041 Uiso 1 1 calc R . . C10 C 0.6386(3) 0.2103(2) 0.21641(11) 0.0302(4) Uani 1 1 d . . . C11 C 0.8151(4) 0.0738(2) 0.18012(12) 0.0349(4) Uani 1 1 d . . . H11 H 0.7907 -0.0355 0.2002 0.042 Uiso 1 1 calc R . . C12 C 1.0661(4) 0.2501(3) 0.08341(13) 0.0423(5) Uani 1 1 d . . . H12 H 1.2128 0.2613 0.0397 0.051 Uiso 1 1 calc R . . C13 C 0.8939(5) 0.3899(3) 0.11476(14) 0.0440(5) Uani 1 1 d . . . H13 H 0.9209 0.4972 0.0918 0.053 Uiso 1 1 calc R . . C14 C 0.6797(4) 0.3702(2) 0.18070(12) 0.0367(4) Uani 1 1 d . . . H14 H 0.5614 0.4650 0.2015 0.044 Uiso 1 1 calc R . . N1 N 1.0204(3) 0.0977(2) 0.11649(10) 0.0375(4) Uani 1 1 d . . . H1A H 1.1282 0.0104 0.0959 0.045 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 Cl1 0.0588(4) 0.0472(3) 0.0494(3) 0.0024(2) 0.0158(2) 0.0118(2) C1 0.0395(10) 0.0379(10) 0.0386(9) 0.0035(8) 0.0010(8) -0.0154(8) C2 0.0512(12) 0.0358(10) 0.0502(11) -0.0014(8) -0.0045(9) -0.0193(9) C3 0.0468(11) 0.0369(10) 0.0432(10) -0.0099(8) -0.0013(8) -0.0054(8) C4 0.0337(9) 0.0381(9) 0.0339(9) -0.0020(7) 0.0017(7) -0.0046(7) C5 0.0258(8) 0.0313(8) 0.0298(8) 0.0021(6) -0.0011(6) -0.0044(7) C6 0.0265(8) 0.0289(8) 0.0317(8) 0.0040(6) -0.0013(7) -0.0068(6) C7 0.0243(8) 0.0316(8) 0.0303(8) 0.0041(7) 0.0010(6) -0.0048(6) C8 0.0261(8) 0.0347(8) 0.0347(9) 0.0008(7) 0.0032(7) -0.0041(7) C9 0.0306(9) 0.0345(9) 0.0339(8) 0.0013(7) 0.0059(7) -0.0010(7) C10 0.0302(8) 0.0331(8) 0.0264(8) 0.0023(6) 0.0006(6) -0.0042(7) C11 0.0386(10) 0.0318(9) 0.0326(8) 0.0021(7) 0.0043(7) -0.0038(7) C12 0.0368(10) 0.0571(12) 0.0316(9) 0.0046(8) 0.0090(8) -0.0095(9) C13 0.0549(12) 0.0391(10) 0.0363(9) 0.0092(8) 0.0089(9) -0.0102(9) C14 0.0410(10) 0.0338(9) 0.0327(9) 0.0025(7) 0.0044(7) -0.0011(8) N1 0.0354(8) 0.0426(8) 0.0307(7) -0.0023(6) 0.0053(6) 0.0031(7) _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 1.357(3) . ? C1 C6 1.426(2) . ? C1 H1 0.9300 . ? C2 C3 1.415(3) . ? C2 H2 0.9300 . ? C3 C4 1.349(3) . ? C3 H3 0.9300 . ? C4 C5 1.432(2) . ? C4 H4 0.9300 . ? C5 C7 1.407(2) 2_556 ? C5 C6 1.438(2) . ? C6 C7 1.416(2) . ? C7 C5 1.407(2) 2_556 ? C7 C8 1.480(2) . ? C8 C9 1.319(3) . ? C8 H8 0.9300 . ? C9 C10 1.471(2) . ? C9 H9 0.9300 . ? C10 C11 1.383(2) . ? C10 C14 1.393(2) . ? C11 N1 1.336(2) . ? C11 H11 0.9300 . ? C12 N1 1.333(3) . ? C12 C13 1.369(3) . ? C12 H12 0.9300 . ? C13 C14 1.381(3) . ? C13 H13 0.9300 . ? C14 H14 0.9300 . ? N1 H1A 0.8600 . ? 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 121.72(17) . . ? C2 C1 H1 119.1 . . ? C6 C1 H1 119.1 . . ? C1 C2 C3 120.28(17) . . ? C1 C2 H2 119.9 . . ? C3 C2 H2 119.9 . . ? C4 C3 C2 120.30(17) . . ? C4 C3 H3 119.8 . . ? C2 C3 H3 119.8 . . ? C3 C4 C5 121.61(17) . . ? C3 C4 H4 119.2 . . ? C5 C4 H4 119.2 . . ? C7 C5 C4 120.94(15) 2_556 . ? C7 C5 C6 120.81(15) 2_556 . ? C4 C5 C6 118.19(15) . . ? C7 C6 C1 122.55(15) . . ? C7 C6 C5 119.49(15) . . ? C1 C6 C5 117.85(15) . . ? C5 C7 C6 119.69(15) 2_556 . ? C5 C7 C8 118.18(15) 2_556 . ? C6 C7 C8 122.06(15) . . ? C9 C8 C7 126.99(16) . . ? C9 C8 H8 116.5 . . ? C7 C8 H8 116.5 . . ? C8 C9 C10 125.41(16) . . ? C8 C9 H9 117.3 . . ? C10 C9 H9 117.3 . . ? C11 C10 C14 116.91(15) . . ? C11 C10 C9 122.39(16) . . ? C14 C10 C9 120.67(15) . . ? N1 C11 C10 120.55(16) . . ? N1 C11 H11 119.7 . . ? C10 C11 H11 119.7 . . ? N1 C12 C13 118.97(16) . . ? N1 C12 H12 120.5 . . ? C13 C12 H12 120.5 . . ? C12 C13 C14 119.48(17) . . ? C12 C13 H13 120.3 . . ? C14 C13 H13 120.3 . . ? C13 C14 C10 120.85(17) . . ? C13 C14 H14 119.6 . . ? C10 C14 H14 119.6 . . ? C12 N1 C11 123.19(16) . . ? C12 N1 H1A 118.4 . . ? C11 N1 H1A 118.4 . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1A Cl1 0.86 2.16 2.9838(19) 159.6 . _diffrn_measured_fraction_theta_max 0.983 _diffrn_reflns_theta_full 27.46 _diffrn_measured_fraction_theta_full 0.983 _refine_diff_density_max 0.298 _refine_diff_density_min -0.310 _refine_diff_density_rms 0.058 data_dyj-15 _database_code_depnum_ccdc_archive 'CCDC 919149' #TrackingRef 'CCDC919149_revised.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C28 H20 N2' _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 7.3295(15) _cell_length_b 6.3418(13) _cell_length_c 21.422(4) _cell_angle_alpha 90.00 _cell_angle_beta 91.26(3) _cell_angle_gamma 90.00 _cell_volume 995.5(4) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 5852 _cell_measurement_theta_min 3.34 _cell_measurement_theta_max 27.54 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.19 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.283 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 404 _exptl_absorpt_coefficient_mu 0.075 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9710 _exptl_absorpt_correction_T_max 0.9862 _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 'Rigaku RAXIS-RAPID' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9378 _diffrn_reflns_av_R_equivalents 0.0336 _diffrn_reflns_av_unetI/netI 0.0294 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 3.33 _diffrn_reflns_theta_max 27.48 _reflns_number_total 2283 _reflns_number_gt 1683 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'RAPID-AUTO (Rigaku Corporation, 1998)' _computing_cell_refinement RAPID-AUTO _computing_data_reduction 'CrystalStructure (Rigaku/MSC and Rigaku Corporation, 2002)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material SHELXL-97 _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^)+(0.0623P)^2^+0.1254P] 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 2283 _refine_ls_number_parameters 136 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0623 _refine_ls_R_factor_gt 0.0434 _refine_ls_wR_factor_ref 0.1219 _refine_ls_wR_factor_gt 0.1109 _refine_ls_goodness_of_fit_ref 1.029 _refine_ls_restrained_S_all 1.029 _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 0.2674(2) 0.1000(2) 0.24566(7) 0.0497(4) Uani 1 1 d . . . H1 H 0.2503 -0.0105 0.2735 0.060 Uiso 1 1 calc R . . C2 C 0.4071(2) 0.0843(2) 0.20390(7) 0.0475(4) Uani 1 1 d . . . H2 H 0.4830 -0.0332 0.2040 0.057 Uiso 1 1 calc R . . C3 C 0.4321(2) 0.2456(2) 0.16202(6) 0.0426(3) Uani 1 1 d . . . H3 H 0.5251 0.2378 0.1333 0.051 Uiso 1 1 calc R . . C4 C 0.31779(18) 0.4203(2) 0.16292(6) 0.0368(3) Uani 1 1 d . . . C5 C 0.18241(19) 0.4196(2) 0.20758(6) 0.0435(3) Uani 1 1 d . . . H5 H 0.1052 0.5357 0.2090 0.052 Uiso 1 1 calc R . . C6 C 0.33322(19) 0.6002(2) 0.12038(6) 0.0407(3) Uani 1 1 d . . . H6 H 0.2408 0.7005 0.1216 0.049 Uiso 1 1 calc R . . C7 C 0.46477(19) 0.6346(2) 0.08049(6) 0.0414(3) Uani 1 1 d . . . H7 H 0.5560 0.5332 0.0783 0.050 Uiso 1 1 calc R . . C8 C 0.48009(18) 0.8199(2) 0.03899(6) 0.0370(3) Uani 1 1 d . . . C9 C 0.63647(18) 0.9475(2) 0.04478(6) 0.0376(3) Uani 1 1 d . . . C10 C 0.65661(19) 1.1302(2) 0.00591(6) 0.0387(3) Uani 1 1 d . . . C11 C 0.8124(2) 1.2605(3) 0.01691(7) 0.0514(4) Uani 1 1 d . . . H11 H 0.8281 1.3797 -0.0077 0.062 Uiso 1 1 calc R . . C12 C 0.9381(2) 1.2153(3) 0.06219(8) 0.0619(5) Uani 1 1 d . . . H12 H 1.0384 1.3036 0.0681 0.074 Uiso 1 1 calc R . . C13 C 0.9189(2) 1.0369(3) 0.10025(7) 0.0569(4) Uani 1 1 d . . . H13 H 1.0060 1.0077 0.1313 0.068 Uiso 1 1 calc R . . C14 C 0.7736(2) 0.9072(2) 0.09177(6) 0.0464(4) Uani 1 1 d . . . H14 H 0.7627 0.7891 0.1171 0.056 Uiso 1 1 calc R . . N1 N 0.15564(18) 0.2649(2) 0.24828(6) 0.0521(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 0.0541(9) 0.0493(8) 0.0456(8) 0.0104(7) -0.0018(7) -0.0053(7) C2 0.0528(9) 0.0402(8) 0.0491(8) 0.0017(6) -0.0045(7) 0.0045(6) C3 0.0470(8) 0.0421(7) 0.0391(7) -0.0020(6) 0.0060(6) 0.0034(6) C4 0.0379(7) 0.0384(7) 0.0340(6) -0.0028(5) -0.0005(5) -0.0025(5) C5 0.0385(7) 0.0449(8) 0.0474(7) 0.0016(6) 0.0060(6) 0.0013(6) C6 0.0425(8) 0.0371(7) 0.0425(7) -0.0003(6) 0.0026(6) 0.0021(6) C7 0.0446(8) 0.0381(7) 0.0418(7) 0.0007(6) 0.0032(6) 0.0031(6) C8 0.0410(7) 0.0370(7) 0.0332(6) -0.0014(5) 0.0058(5) 0.0016(5) C9 0.0400(7) 0.0396(7) 0.0334(6) -0.0028(5) 0.0044(5) 0.0019(5) C10 0.0414(7) 0.0401(7) 0.0346(6) -0.0028(6) 0.0048(5) -0.0020(6) C11 0.0528(9) 0.0532(9) 0.0480(8) 0.0046(7) -0.0023(7) -0.0148(7) C12 0.0527(10) 0.0723(11) 0.0601(9) 0.0040(9) -0.0112(8) -0.0212(8) C13 0.0478(9) 0.0707(11) 0.0515(8) 0.0022(8) -0.0125(7) -0.0017(8) C14 0.0458(8) 0.0508(8) 0.0425(7) 0.0031(6) -0.0011(6) 0.0037(6) N1 0.0489(7) 0.0581(8) 0.0497(7) 0.0076(6) 0.0094(6) -0.0041(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 1.330(2) . ? C1 C2 1.378(2) . ? C1 H1 0.9300 . ? C2 C3 1.3756(19) . ? C2 H2 0.9300 . ? C3 C4 1.3892(18) . ? C3 H3 0.9300 . ? C4 C5 1.3933(18) . ? C4 C6 1.4663(18) . ? C5 N1 1.3300(18) . ? C5 H5 0.9300 . ? C6 C7 1.320(2) . ? C6 H6 0.9300 . ? C7 C8 1.4792(18) . ? C7 H7 0.9300 . ? C8 C9 1.4062(19) . ? C8 C10 1.4097(19) 3_675 ? C9 C14 1.4297(19) . ? C9 C10 1.4362(18) . ? C10 C8 1.4097(19) 3_675 ? C10 C11 1.425(2) . ? C11 C12 1.354(2) . ? C11 H11 0.9300 . ? C12 C13 1.404(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 123.46(13) . . ? N1 C1 H1 118.3 . . ? C2 C1 H1 118.3 . . ? C3 C2 C1 118.76(14) . . ? C3 C2 H2 120.6 . . ? C1 C2 H2 120.6 . . ? C2 C3 C4 119.67(13) . . ? C2 C3 H3 120.2 . . ? C4 C3 H3 120.2 . . ? C3 C4 C5 116.46(12) . . ? C3 C4 C6 123.87(12) . . ? C5 C4 C6 119.66(12) . . ? N1 C5 C4 124.76(13) . . ? N1 C5 H5 117.6 . . ? C4 C5 H5 117.6 . . ? C7 C6 C4 126.72(13) . . ? C7 C6 H6 116.6 . . ? C4 C6 H6 116.6 . . ? C6 C7 C8 125.89(13) . . ? C6 C7 H7 117.1 . . ? C8 C7 H7 117.1 . . ? C9 C8 C10 119.77(12) . 3_675 ? C9 C8 C7 118.46(12) . . ? C10 C8 C7 121.76(12) 3_675 . ? C8 C9 C14 121.21(12) . . ? C8 C9 C10 120.46(12) . . ? C14 C9 C10 118.21(12) . . ? C8 C10 C11 122.51(13) 3_675 . ? C8 C10 C9 119.76(12) 3_675 . ? C11 C10 C9 117.66(13) . . ? C12 C11 C10 121.75(14) . . ? C12 C11 H11 119.1 . . ? C10 C11 H11 119.1 . . ? C11 C12 C13 120.76(15) . . ? C11 C12 H12 119.6 . . ? C13 C12 H12 119.6 . . ? C14 C13 C12 120.00(14) . . ? C14 C13 H13 120.0 . . ? C12 C13 H13 120.0 . . ? C13 C14 C9 121.63(14) . . ? C13 C14 H14 119.2 . . ? C9 C14 H14 119.2 . . ? C5 N1 C1 116.89(13) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.131 _refine_diff_density_min -0.159 _refine_diff_density_rms 0.034