# Electronic Supplementary Material (ESI) for Chemical Science # This journal is © The Royal Society of Chemistry 2012 data_global _journal_coden_Cambridge 1475 loop_ _publ_author_name 'Meisner, Jeffrey' 'Sedbrook, Danielle' 'Krikorian, Markrete' 'Jun Chen.' 'Carnes, Matthew' 'Steigerwald, M.L.' 'Murray, Christopher' 'Nuckolls, Colin' _publ_contact_author_name 'Nuckolls, Colin' _publ_contact_author_email cn37@columbia.edu _publ_section_title ; Functionalizing Molecular Wires: A Tunable Class of a,o-diphenyl- m,n-dicyano-oligoenes ; data_DPDC11 _database_code_depnum_ccdc_archive 'CCDC 847946' #TrackingRef '- DPDC11.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C37 H32 Cl2 N2' _chemical_formula_weight 575.55 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 Monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 28.982(6) _cell_length_b 11.074(2) _cell_length_c 9.7067(19) _cell_angle_alpha 90.00 _cell_angle_beta 101.660(3) _cell_angle_gamma 90.00 _cell_volume 3051.1(10) _cell_formula_units_Z 4 _cell_measurement_temperature 125(2) _cell_measurement_reflns_used 2654 _cell_measurement_theta_min 2.80 _cell_measurement_theta_max 30.17 _exptl_crystal_description NEEDLE _exptl_crystal_colour BLACK _exptl_crystal_size_max 0.48 _exptl_crystal_size_mid 0.03 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.253 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1208 _exptl_absorpt_coefficient_mu 0.241 _exptl_absorpt_correction_type EMPIRICAL _exptl_absorpt_correction_T_min 0.8930 _exptl_absorpt_correction_T_max 0.9976 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 125(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 17492 _diffrn_reflns_av_R_equivalents 0.2683 _diffrn_reflns_av_sigmaI/netI 0.3050 _diffrn_reflns_limit_h_min -41 _diffrn_reflns_limit_h_max 40 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.43 _diffrn_reflns_theta_max 30.52 _reflns_number_total 4613 _reflns_number_gt 1469 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0297P)^2^+7.7440P] 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 SHELXL _refine_ls_extinction_coef 0.00043(15) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4613 _refine_ls_number_parameters 187 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2865 _refine_ls_R_factor_gt 0.0821 _refine_ls_wR_factor_ref 0.1812 _refine_ls_wR_factor_gt 0.1341 _refine_ls_goodness_of_fit_ref 1.001 _refine_ls_restrained_S_all 1.001 _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 N N 0.05811(13) 0.2687(4) 0.8577(4) 0.0326(10) Uani 1 1 d . . . C1 C 0.34121(15) 0.5227(4) 0.0873(5) 0.0284(11) Uani 1 1 d . . . H1A H 0.3316 0.4624 0.1454 0.034 Uiso 1 1 calc R . . C2 C 0.37516(15) 0.4957(4) 0.0116(5) 0.0338(12) Uani 1 1 d . . . H2A H 0.3887 0.4173 0.0172 0.041 Uiso 1 1 calc R . . C3 C 0.38962(15) 0.5831(4) -0.0732(5) 0.0328(12) Uani 1 1 d . . . H3A H 0.4137 0.5650 -0.1233 0.039 Uiso 1 1 calc R . . C4 C 0.36919(15) 0.6956(4) -0.0850(5) 0.0334(12) Uani 1 1 d . . . H4A H 0.3783 0.7548 -0.1451 0.040 Uiso 1 1 calc R . . C5 C 0.33515(16) 0.7212(4) -0.0080(5) 0.0345(12) Uani 1 1 d . . . H5A H 0.3212 0.7992 -0.0156 0.041 Uiso 1 1 calc R . . C6 C 0.32062(14) 0.6365(4) 0.0805(4) 0.0242(10) Uani 1 1 d . . . C7 C 0.28599(15) 0.6735(4) 0.1627(4) 0.0267(11) Uani 1 1 d . . . H7A H 0.2750 0.7543 0.1495 0.032 Uiso 1 1 calc R . . C8 C 0.26777(14) 0.6065(4) 0.2555(4) 0.0249(11) Uani 1 1 d . . . H8A H 0.2769 0.5243 0.2689 0.030 Uiso 1 1 calc R . . C9 C 0.23512(14) 0.6548(4) 0.3346(4) 0.0259(11) Uani 1 1 d . . . H9A H 0.2263 0.7372 0.3200 0.031 Uiso 1 1 calc R . . C10 C 0.21610(14) 0.5921(4) 0.4277(4) 0.0268(11) Uani 1 1 d . . . H10A H 0.2245 0.5095 0.4413 0.032 Uiso 1 1 calc R . . C11 C 0.18407(14) 0.6407(4) 0.5079(4) 0.0241(10) Uani 1 1 d . . . H11A H 0.1770 0.7245 0.4993 0.029 Uiso 1 1 calc R . . C12 C 0.16320(14) 0.5744(4) 0.5953(4) 0.0231(10) Uani 1 1 d . . . H12A H 0.1713 0.4913 0.6048 0.028 Uiso 1 1 calc R . . C13 C 0.13032(14) 0.6174(4) 0.6742(4) 0.0241(10) Uani 1 1 d . . . H13A H 0.1241 0.7016 0.6753 0.029 Uiso 1 1 calc R . . C14 C 0.10765(14) 0.5420(4) 0.7477(4) 0.0235(10) Uani 1 1 d . . . H14A H 0.1151 0.4585 0.7465 0.028 Uiso 1 1 calc R . . C15 C 0.07329(14) 0.5773(4) 0.8271(4) 0.0242(10) Uani 1 1 d . . . H15A H 0.0681 0.6613 0.8369 0.029 Uiso 1 1 calc R . . C16 C 0.04759(15) 0.4999(4) 0.8894(4) 0.0238(10) Uani 1 1 d . . . C17 C 0.01353(14) 0.5378(4) 0.9706(4) 0.0255(11) Uani 1 1 d . . . H17A H 0.0099 0.6220 0.9836 0.031 Uiso 1 1 calc R . . C18 C 0.05361(14) 0.3704(5) 0.8719(4) 0.0259(10) Uani 1 1 d . . . Cl Cl 0.02042(5) 0.13163(12) 0.12465(14) 0.0446(4) Uani 1 1 d . . . C19 C 0.0000 0.0412(6) 0.2500 0.0431(19) Uani 1 2 d S . . H19A H 0.0252 -0.0097 0.2969 0.052 Uiso 1 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 N 0.031(2) 0.030(2) 0.042(3) 0.001(2) 0.0187(19) -0.0023(19) C1 0.034(3) 0.025(3) 0.030(3) 0.002(2) 0.015(2) -0.003(2) C2 0.034(3) 0.028(3) 0.042(3) 0.001(2) 0.015(2) 0.007(2) C3 0.029(3) 0.040(3) 0.035(3) -0.001(2) 0.020(2) 0.000(2) C4 0.038(3) 0.026(3) 0.047(3) 0.009(2) 0.031(3) 0.002(2) C5 0.043(3) 0.025(3) 0.041(3) -0.002(2) 0.023(3) 0.001(2) C6 0.025(2) 0.024(2) 0.026(2) -0.004(2) 0.010(2) -0.001(2) C7 0.035(3) 0.018(2) 0.030(3) -0.002(2) 0.013(2) -0.001(2) C8 0.026(2) 0.025(3) 0.024(2) -0.003(2) 0.008(2) -0.005(2) C9 0.029(3) 0.026(3) 0.025(2) -0.004(2) 0.012(2) -0.006(2) C10 0.023(2) 0.032(3) 0.028(3) -0.009(2) 0.012(2) -0.003(2) C11 0.029(2) 0.019(2) 0.027(2) 0.000(2) 0.012(2) 0.000(2) C12 0.029(3) 0.021(2) 0.024(2) -0.002(2) 0.015(2) -0.006(2) C13 0.028(2) 0.022(2) 0.024(2) -0.002(2) 0.010(2) 0.000(2) C14 0.025(3) 0.023(2) 0.024(3) 0.000(2) 0.010(2) 0.0008(19) C15 0.025(2) 0.027(2) 0.023(2) 0.002(2) 0.009(2) 0.006(2) C16 0.026(2) 0.027(3) 0.019(2) 0.004(2) 0.008(2) 0.006(2) C17 0.026(3) 0.032(3) 0.020(2) 0.004(2) 0.009(2) 0.009(2) C18 0.019(2) 0.038(3) 0.026(3) 0.007(2) 0.0147(19) -0.005(2) Cl 0.0534(8) 0.0317(7) 0.0572(9) 0.0021(7) 0.0314(7) -0.0002(7) C19 0.049(5) 0.025(4) 0.066(5) 0.000 0.036(4) 0.000 _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 N C18 1.145(5) . ? C1 C2 1.375(6) . ? C1 C6 1.390(6) . ? C2 C3 1.389(6) . ? C3 C4 1.374(6) . ? C4 C5 1.382(6) . ? C5 C6 1.393(6) . ? C6 C7 1.462(5) . ? C7 C8 1.354(5) . ? C8 C9 1.437(5) . ? C9 C10 1.343(5) . ? C10 C11 1.432(5) . ? C11 C12 1.354(5) . ? C12 C13 1.420(5) . ? C13 C14 1.352(5) . ? C14 C15 1.431(5) . ? C15 C16 1.355(5) . ? C16 C17 1.444(5) . ? C16 C18 1.459(6) . ? C17 C17 1.350(8) 5_567 ? Cl C19 1.767(4) . ? C19 Cl 1.767(4) 2 ? 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 121.2(4) . . ? C1 C2 C3 120.0(4) . . ? C4 C3 C2 120.3(4) . . ? C3 C4 C5 118.9(4) . . ? C4 C5 C6 122.2(4) . . ? C1 C6 C5 117.4(4) . . ? C1 C6 C7 124.3(4) . . ? C5 C6 C7 118.3(4) . . ? C8 C7 C6 127.8(4) . . ? C7 C8 C9 122.6(4) . . ? C10 C9 C8 124.8(4) . . ? C9 C10 C11 124.8(4) . . ? C12 C11 C10 123.9(4) . . ? C11 C12 C13 126.1(4) . . ? C14 C13 C12 121.9(4) . . ? C13 C14 C15 125.5(4) . . ? C16 C15 C14 124.9(4) . . ? C15 C16 C17 123.9(4) . . ? C15 C16 C18 118.7(4) . . ? C17 C16 C18 117.4(4) . . ? C17 C17 C16 124.7(5) 5_567 . ? N C18 C16 179.7(6) . . ? Cl C19 Cl 111.0(4) . 2 ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 30.52 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.340 _refine_diff_density_min -0.405 _refine_diff_density_rms 0.084 # Attachment '- DPDC13.cif' data_DPDC13 _database_code_depnum_ccdc_archive 'CCDC 847947' #TrackingRef '- DPDC13.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C41 H35 Cl2 N2' _chemical_formula_weight 626.61 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 Monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 32.920(13) _cell_length_b 11.005(4) _cell_length_c 9.624(4) _cell_angle_alpha 90.00 _cell_angle_beta 106.563(6) _cell_angle_gamma 90.00 _cell_volume 3342(2) _cell_formula_units_Z 4 _cell_measurement_temperature 125(2) _cell_measurement_reflns_used 1460 _cell_measurement_theta_min 2.81 _cell_measurement_theta_max 24.55 _exptl_crystal_description NEEDLE _exptl_crystal_colour BLACK _exptl_crystal_size_max 0.41 _exptl_crystal_size_mid 0.02 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.245 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1316 _exptl_absorpt_coefficient_mu 0.226 _exptl_absorpt_correction_type EMPIRICAL _exptl_absorpt_correction_T_min 0.9130 _exptl_absorpt_correction_T_max 0.9977 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 125(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 22453 _diffrn_reflns_av_R_equivalents 0.2928 _diffrn_reflns_av_sigmaI/netI 0.2410 _diffrn_reflns_limit_h_min -43 _diffrn_reflns_limit_h_max 43 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 1.29 _diffrn_reflns_theta_max 28.28 _reflns_number_total 4152 _reflns_number_gt 1358 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.1000P)^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 SHELXL _refine_ls_extinction_coef 0.0007(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4152 _refine_ls_number_parameters 205 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2737 _refine_ls_R_factor_gt 0.0837 _refine_ls_wR_factor_ref 0.2638 _refine_ls_wR_factor_gt 0.1900 _refine_ls_goodness_of_fit_ref 1.001 _refine_ls_restrained_S_all 1.001 _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 N N 0.05261(15) -0.2305(5) -0.7672(5) 0.0377(12) Uani 1 1 d . . . C1 C 0.35419(17) 0.0203(5) 0.6741(6) 0.0325(14) Uani 1 1 d . . . H1A H 0.3452 -0.0401 0.6012 0.039 Uiso 1 1 calc R . . C2 C 0.38539(18) -0.0068(5) 0.7988(6) 0.0409(15) Uani 1 1 d . . . H2A H 0.3979 -0.0853 0.8106 0.049 Uiso 1 1 calc R . . C3 C 0.39877(18) 0.0784(5) 0.9072(6) 0.0389(15) Uani 1 1 d . . . H3A H 0.4205 0.0590 0.9930 0.047 Uiso 1 1 calc R . . C4 C 0.38041(19) 0.1915(5) 0.8902(6) 0.0391(16) Uani 1 1 d . . . H4A H 0.3892 0.2506 0.9648 0.047 Uiso 1 1 calc R . . C5 C 0.34917(18) 0.2192(5) 0.7642(6) 0.0368(15) Uani 1 1 d . . . H5A H 0.3367 0.2978 0.7533 0.044 Uiso 1 1 calc R . . C6 C 0.33553(17) 0.1343(5) 0.6525(5) 0.0298(13) Uani 1 1 d . . . C7 C 0.30428(17) 0.1716(5) 0.5188(5) 0.0307(13) Uani 1 1 d . . . H7A H 0.2946 0.2531 0.5165 0.037 Uiso 1 1 calc R . . C8 C 0.28737(16) 0.1060(5) 0.3985(5) 0.0293(13) Uani 1 1 d . . . H8A H 0.2947 0.0226 0.3977 0.035 Uiso 1 1 calc R . . C9 C 0.25870(17) 0.1573(5) 0.2715(5) 0.0312(13) Uani 1 1 d . . . H9A H 0.2515 0.2406 0.2751 0.037 Uiso 1 1 calc R . . C10 C 0.24096(16) 0.0960(5) 0.1458(5) 0.0283(13) Uani 1 1 d . . . H10A H 0.2474 0.0121 0.1422 0.034 Uiso 1 1 calc R . . C11 C 0.21327(16) 0.1503(5) 0.0193(5) 0.0285(13) Uani 1 1 d . . . H11A H 0.2080 0.2350 0.0220 0.034 Uiso 1 1 calc R . . C12 C 0.19405(16) 0.0900(5) -0.1036(5) 0.0286(13) Uani 1 1 d . . . H12A H 0.1994 0.0053 -0.1054 0.034 Uiso 1 1 calc R . . C13 C 0.16622(16) 0.1428(5) -0.2323(5) 0.0256(12) Uani 1 1 d . . . H13A H 0.1616 0.2280 -0.2338 0.031 Uiso 1 1 calc R . . C14 C 0.14643(16) 0.0784(5) -0.3505(5) 0.0283(13) Uani 1 1 d . . . H14A H 0.1524 -0.0062 -0.3467 0.034 Uiso 1 1 calc R . . C15 C 0.11756(16) 0.1215(5) -0.4811(5) 0.0260(12) Uani 1 1 d . . . H15A H 0.1128 0.2064 -0.4938 0.031 Uiso 1 1 calc R . . C16 C 0.09673(16) 0.0451(5) -0.5874(5) 0.0266(13) Uani 1 1 d . . . H16A H 0.1028 -0.0390 -0.5727 0.032 Uiso 1 1 calc R . . C17 C 0.06665(16) 0.0789(5) -0.7188(5) 0.0277(13) Uani 1 1 d . . . H17A H 0.0627 0.1634 -0.7384 0.033 Uiso 1 1 calc R . . C18 C 0.04287(17) 0.0013(5) -0.8194(5) 0.0289(13) Uani 1 1 d . . . C19 C 0.01238(16) 0.0380(5) -0.9511(5) 0.0281(13) Uani 1 1 d . . . H19A H 0.0094 0.1226 -0.9709 0.034 Uiso 1 1 calc R . . C20 C 0.04843(16) -0.1283(6) -0.7894(5) 0.0299(13) Uani 1 1 d . . . Cl Cl 0.01840(6) 0.36970(15) 0.40644(18) 0.0594(6) Uani 1 1 d . . . C21 C 0.0000 0.4627(8) 0.2500 0.050(3) Uani 1 2 d S . . H21A H 0.0318 0.5070 0.2539 0.060 Uiso 0.50 1 d PR . . 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 N 0.042(3) 0.038(3) 0.028(3) 0.002(2) 0.001(2) 0.002(3) C1 0.036(3) 0.028(3) 0.031(3) 0.000(2) 0.005(3) 0.002(3) C2 0.047(4) 0.037(3) 0.039(4) 0.004(3) 0.013(3) 0.013(3) C3 0.037(4) 0.046(4) 0.029(3) 0.003(3) 0.002(3) 0.007(3) C4 0.049(4) 0.036(4) 0.024(3) -0.006(3) -0.003(3) -0.005(3) C5 0.048(4) 0.027(3) 0.031(3) 0.002(3) 0.003(3) -0.001(3) C6 0.032(3) 0.035(3) 0.021(3) 0.000(3) 0.006(2) -0.003(3) C7 0.039(3) 0.026(3) 0.027(3) -0.001(2) 0.011(3) -0.002(3) C8 0.031(3) 0.030(3) 0.027(3) -0.003(2) 0.009(3) -0.003(2) C9 0.036(3) 0.031(3) 0.025(3) 0.002(3) 0.005(3) -0.002(3) C10 0.032(3) 0.025(3) 0.026(3) 0.002(2) 0.006(3) 0.000(2) C11 0.031(3) 0.028(3) 0.023(3) 0.001(2) 0.002(2) -0.004(3) C12 0.031(3) 0.028(3) 0.025(3) 0.003(2) 0.005(3) -0.002(2) C13 0.031(3) 0.024(3) 0.021(3) 0.001(2) 0.006(2) 0.002(2) C14 0.033(3) 0.024(3) 0.026(3) 0.003(2) 0.005(3) 0.000(2) C15 0.027(3) 0.029(3) 0.021(3) 0.001(2) 0.006(2) 0.001(3) C16 0.027(3) 0.029(3) 0.022(3) 0.005(2) 0.003(2) 0.005(2) C17 0.034(3) 0.027(3) 0.025(3) 0.003(2) 0.014(3) 0.002(3) C18 0.035(3) 0.033(3) 0.019(3) 0.001(2) 0.008(3) 0.007(3) C19 0.030(3) 0.034(3) 0.019(3) 0.001(2) 0.006(2) 0.007(2) C20 0.027(3) 0.043(4) 0.016(3) -0.004(3) 0.000(2) 0.001(3) Cl 0.0733(13) 0.0427(10) 0.0545(11) 0.0012(8) 0.0059(9) -0.0005(9) C21 0.047(6) 0.038(5) 0.049(6) 0.000 -0.014(5) 0.000 _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 N C20 1.145(7) . ? C1 C2 1.372(7) . ? C1 C6 1.386(7) . ? C2 C3 1.379(8) . ? C3 C4 1.373(8) . ? C4 C5 1.382(7) . ? C5 C6 1.398(7) . ? C6 C7 1.459(7) . ? C7 C8 1.343(7) . ? C8 C9 1.430(7) . ? C9 C10 1.363(7) . ? C10 C11 1.428(7) . ? C11 C12 1.346(7) . ? C12 C13 1.436(7) . ? C13 C14 1.341(7) . ? C14 C15 1.423(7) . ? C15 C16 1.350(7) . ? C16 C17 1.415(7) . ? C17 C18 1.359(7) . ? C18 C19 1.432(7) . ? C18 C20 1.456(8) . ? C19 C19 1.347(10) 5_553 ? Cl C21 1.778(5) . ? C21 Cl 1.778(5) 2 ? 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 121.1(5) . . ? C1 C2 C3 120.8(5) . . ? C4 C3 C2 119.4(5) . . ? C3 C4 C5 119.8(5) . . ? C4 C5 C6 121.5(5) . . ? C1 C6 C5 117.3(5) . . ? C1 C6 C7 123.9(5) . . ? C5 C6 C7 118.8(5) . . ? C8 C7 C6 128.6(5) . . ? C7 C8 C9 122.4(5) . . ? C10 C9 C8 125.1(5) . . ? C9 C10 C11 123.9(5) . . ? C12 C11 C10 124.7(5) . . ? C11 C12 C13 125.7(5) . . ? C14 C13 C12 123.7(5) . . ? C13 C14 C15 127.8(5) . . ? C16 C15 C14 121.9(5) . . ? C15 C16 C17 126.1(5) . . ? C18 C17 C16 125.9(5) . . ? C17 C18 C19 124.7(5) . . ? C17 C18 C20 117.4(5) . . ? C19 C18 C20 117.9(5) . . ? C19 C19 C18 125.1(7) 5_553 . ? N C20 C18 179.4(6) . . ? Cl C21 Cl 109.7(5) 2 . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 28.28 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.334 _refine_diff_density_min -0.503 _refine_diff_density_rms 0.083 # Attachment '- DPDC3.cif' data_DPDC3 _database_code_depnum_ccdc_archive 'CCDC 847948' #TrackingRef '- DPDC3.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H14 N2' _chemical_formula_weight 282.33 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 10.7874(15) _cell_length_b 6.1038(8) _cell_length_c 11.5494(16) _cell_angle_alpha 90.00 _cell_angle_beta 104.177(2) _cell_angle_gamma 90.00 _cell_volume 737.30(17) _cell_formula_units_Z 2 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used 8716 _cell_measurement_theta_min 2.32 _cell_measurement_theta_max 32.49 _exptl_crystal_description BLOCK _exptl_crystal_colour COLORLESS _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.272 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 296 _exptl_absorpt_coefficient_mu 0.075 _exptl_absorpt_correction_type EMPIRICAL _exptl_absorpt_correction_T_min 0.9705 _exptl_absorpt_correction_T_max 0.9777 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 123(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 12221 _diffrn_reflns_av_R_equivalents 0.0188 _diffrn_reflns_av_sigmaI/netI 0.0136 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.32 _diffrn_reflns_theta_max 32.66 _reflns_number_total 2590 _reflns_number_gt 2341 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0785P)^2^+0.1030P] 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 2590 _refine_ls_number_parameters 100 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0441 _refine_ls_R_factor_gt 0.0409 _refine_ls_wR_factor_ref 0.1224 _refine_ls_wR_factor_gt 0.1187 _refine_ls_goodness_of_fit_ref 1.062 _refine_ls_restrained_S_all 1.062 _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 N N 0.30830(7) -0.45219(12) 0.45439(7) 0.02848(18) Uani 1 1 d . . . C1 C 0.09155(7) -0.24053(12) 0.60767(6) 0.02042(16) Uani 1 1 d . . . H1A H 0.1321 -0.3480 0.5701 0.025 Uiso 1 1 calc R . . C2 C -0.02062(7) -0.29210(13) 0.64046(7) 0.02279(16) Uani 1 1 d . . . H2A H -0.0566 -0.4342 0.6242 0.027 Uiso 1 1 calc R . . C3 C -0.08089(7) -0.13869(14) 0.69670(7) 0.02406(17) Uani 1 1 d . . . H3A H -0.1579 -0.1753 0.7183 0.029 Uiso 1 1 calc R . . C4 C -0.02780(7) 0.06871(14) 0.72119(7) 0.02547(17) Uani 1 1 d . . . H4A H -0.0676 0.1739 0.7608 0.031 Uiso 1 1 calc R . . C5 C 0.08383(7) 0.12189(12) 0.68751(7) 0.02174(16) Uani 1 1 d . . . H5A H 0.1191 0.2644 0.7040 0.026 Uiso 1 1 calc R . . C6 C 0.14546(6) -0.03030(11) 0.62970(6) 0.01697(15) Uani 1 1 d . . . C7 C 0.26165(6) 0.04333(11) 0.59840(6) 0.01756(15) Uani 1 1 d . . . H7A H 0.2854 0.1899 0.6213 0.021 Uiso 1 1 calc R . . C8 C 0.34199(6) -0.06042(11) 0.54226(6) 0.01676(15) Uani 1 1 d . . . C9 C 0.45636(6) 0.04803(11) 0.52471(6) 0.01777(15) Uani 1 1 d . . . H9A H 0.4704 0.1962 0.5497 0.021 Uiso 1 1 calc R . . C10 C 0.32022(6) -0.27967(12) 0.49551(6) 0.01994(16) 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 N 0.0246(3) 0.0242(3) 0.0410(4) -0.0070(3) 0.0164(3) -0.0052(2) C1 0.0175(3) 0.0215(3) 0.0240(3) -0.0018(2) 0.0085(2) -0.0025(2) C2 0.0179(3) 0.0263(3) 0.0255(3) 0.0001(3) 0.0078(3) -0.0045(2) C3 0.0175(3) 0.0343(4) 0.0221(3) 0.0013(3) 0.0081(2) -0.0010(3) C4 0.0208(3) 0.0324(4) 0.0261(4) -0.0039(3) 0.0111(3) 0.0010(3) C5 0.0199(3) 0.0231(3) 0.0238(3) -0.0038(2) 0.0082(2) -0.0005(2) C6 0.0146(3) 0.0200(3) 0.0170(3) 0.0003(2) 0.0051(2) -0.0005(2) C7 0.0155(3) 0.0180(3) 0.0198(3) 0.0000(2) 0.0056(2) -0.0015(2) C8 0.0147(3) 0.0173(3) 0.0189(3) 0.0004(2) 0.0053(2) -0.0019(2) C9 0.0151(3) 0.0183(3) 0.0208(3) 0.0003(2) 0.0062(2) -0.0026(2) C10 0.0158(3) 0.0212(3) 0.0250(3) -0.0009(2) 0.0091(2) -0.0026(2) _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 N C10 1.1494(10) . ? C1 C2 1.3897(9) . ? C1 C6 1.4061(10) . ? C2 C3 1.3886(11) . ? C3 C4 1.3897(12) . ? C4 C5 1.3915(10) . ? C5 C6 1.4029(10) . ? C6 C7 1.4580(9) . ? C7 C8 1.3593(9) . ? C8 C10 1.4407(10) . ? C8 C9 1.4573(9) . ? C9 C9 1.3490(13) 3_656 ? 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 120.43(7) . . ? C3 C2 C1 120.89(7) . . ? C2 C3 C4 119.51(7) . . ? C3 C4 C5 119.82(7) . . ? C4 C5 C6 121.47(7) . . ? C5 C6 C1 117.86(6) . . ? C5 C6 C7 116.76(6) . . ? C1 C6 C7 125.38(6) . . ? C8 C7 C6 131.45(6) . . ? C7 C8 C10 123.16(6) . . ? C7 C8 C9 121.00(6) . . ? C10 C8 C9 115.83(6) . . ? C9 C9 C8 124.32(8) 3_656 . ? N C10 C8 175.86(7) . . ? _diffrn_measured_fraction_theta_max 0.958 _diffrn_reflns_theta_full 32.66 _diffrn_measured_fraction_theta_full 0.958 _refine_diff_density_max 0.470 _refine_diff_density_min -0.174 _refine_diff_density_rms 0.050 # Attachment '- DPDC5-CO2H.cif' data_DPDC5-CO2H _database_code_depnum_ccdc_archive 'CCDC 847949' #TrackingRef '- DPDC5-CO2H.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C32 H32 N4 O6' _chemical_formula_weight 568.62 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' O O 0.0106 0.0060 '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 6.2483(10) _cell_length_b 7.1520(11) _cell_length_c 16.741(3) _cell_angle_alpha 101.417(2) _cell_angle_beta 91.557(3) _cell_angle_gamma 92.041(2) _cell_volume 732.4(2) _cell_formula_units_Z 1 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used 3107 _cell_measurement_theta_min 2.48 _cell_measurement_theta_max 30.35 _exptl_crystal_description NEEDLE _exptl_crystal_colour YELLOW _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.289 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 300 _exptl_absorpt_coefficient_mu 0.090 _exptl_absorpt_correction_type EMPIRICAL _exptl_absorpt_correction_T_min 0.9562 _exptl_absorpt_correction_T_max 0.9946 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 200(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 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 11762 _diffrn_reflns_av_R_equivalents 0.0546 _diffrn_reflns_av_sigmaI/netI 0.0821 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 1.24 _diffrn_reflns_theta_max 30.53 _reflns_number_total 4437 _reflns_number_gt 2300 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0399P)^2^+0.0307P] 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 SHELXL _refine_ls_extinction_coef 0.0022(13) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4437 _refine_ls_number_parameters 197 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1291 _refine_ls_R_factor_gt 0.0503 _refine_ls_wR_factor_ref 0.1143 _refine_ls_wR_factor_gt 0.0926 _refine_ls_goodness_of_fit_ref 1.005 _refine_ls_restrained_S_all 1.005 _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 N1 N 0.5454(3) -0.7366(2) -0.00707(10) 0.0483(4) Uani 1 1 d . . . O1 O 0.5579(2) 0.54031(17) 0.27858(8) 0.0389(3) Uani 1 1 d . . . H1 H 0.538(3) 0.663(3) 0.3061(12) 0.067(7) Uiso 1 1 d . . . O2 O 0.8503(2) 0.59470(16) 0.36046(7) 0.0443(4) Uani 1 1 d . . . C1 C 0.7434(3) 0.4907(2) 0.30673(10) 0.0293(4) Uani 1 1 d . . . C2 C 0.8079(3) 0.2964(2) 0.26850(9) 0.0252(4) Uani 1 1 d . . . C3 C 1.0121(3) 0.2450(2) 0.28715(10) 0.0317(4) Uani 1 1 d . . . H3A H 1.1067 0.3352 0.3214 0.038 Uiso 1 1 calc R . . C4 C 1.0795(3) 0.0634(2) 0.25636(10) 0.0312(4) Uani 1 1 d . . . H4A H 1.2198 0.0300 0.2699 0.037 Uiso 1 1 calc R . . C5 C 0.9433(3) -0.0717(2) 0.20542(9) 0.0250(4) Uani 1 1 d . . . C6 C 0.7392(3) -0.0173(2) 0.18577(10) 0.0285(4) Uani 1 1 d . . . H6A H 0.6450 -0.1060 0.1506 0.034 Uiso 1 1 calc R . . C7 C 0.6725(3) 0.1644(2) 0.21685(9) 0.0274(4) Uani 1 1 d . . . H7A H 0.5332 0.1992 0.2028 0.033 Uiso 1 1 calc R . . C8 C 1.0256(3) -0.2603(2) 0.17438(10) 0.0289(4) Uani 1 1 d . . . H8A H 1.1666 -0.2808 0.1926 0.035 Uiso 1 1 calc R . . C9 C 0.9260(3) -0.4076(2) 0.12333(9) 0.0273(4) Uani 1 1 d . . . H9A H 0.7840 -0.3937 0.1042 0.033 Uiso 1 1 calc R . . C10 C 1.0258(3) -0.5850(2) 0.09664(9) 0.0269(4) Uani 1 1 d . . . H10A H 1.1697 -0.5928 0.1151 0.032 Uiso 1 1 calc R . . C11 C 0.9352(2) -0.7431(2) 0.04756(9) 0.0253(4) Uani 1 1 d . . . C12 C 1.0438(3) -0.9195(2) 0.02311(9) 0.0257(4) Uani 1 1 d . . . H12A H 1.1890 -0.9216 0.0412 0.031 Uiso 1 1 calc R . . C13 C 0.7171(3) -0.7381(2) 0.01771(10) 0.0307(4) Uani 1 1 d . . . N2 N 0.6263(2) 1.15021(19) 0.44254(8) 0.0286(3) Uani 1 1 d . . . O3 O 0.48267(19) 0.88744(16) 0.35663(7) 0.0359(3) Uani 1 1 d . . . C14 C 0.6372(3) 0.9791(2) 0.39597(10) 0.0313(4) Uani 1 1 d . . . H14A H 0.7725 0.9220 0.3923 0.038 Uiso 1 1 calc R . . C15 C 0.4265(3) 1.2502(2) 0.44840(11) 0.0363(4) Uani 1 1 d . . . H15A H 0.3087 1.1618 0.4236 0.054 Uiso 1 1 calc R . . H15B H 0.4382 1.3568 0.4197 0.054 Uiso 1 1 calc R . . H15C H 0.3983 1.2992 0.5059 0.054 Uiso 1 1 calc R . . C16 C 0.8126(3) 1.2489(3) 0.48878(11) 0.0407(5) Uani 1 1 d . . . H16A H 0.9358 1.1670 0.4804 0.061 Uiso 1 1 calc R . . H16B H 0.7816 1.2779 0.5469 0.061 Uiso 1 1 calc R . . H16C H 0.8455 1.3679 0.4701 0.061 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 N1 0.0388(10) 0.0353(9) 0.0657(12) -0.0012(8) -0.0101(8) 0.0038(7) O1 0.0360(7) 0.0271(7) 0.0485(8) -0.0052(6) -0.0078(6) 0.0094(6) O2 0.0525(8) 0.0294(7) 0.0434(8) -0.0104(6) -0.0163(6) 0.0119(6) C1 0.0348(10) 0.0244(9) 0.0285(9) 0.0038(7) 0.0006(8) 0.0056(7) C2 0.0304(9) 0.0202(8) 0.0240(8) 0.0015(7) 0.0010(7) 0.0028(7) C3 0.0337(10) 0.0243(9) 0.0332(10) -0.0027(7) -0.0077(8) 0.0015(7) C4 0.0292(9) 0.0259(9) 0.0355(10) -0.0005(7) -0.0058(8) 0.0039(7) C5 0.0314(9) 0.0187(8) 0.0237(9) 0.0016(6) 0.0016(7) 0.0007(7) C6 0.0277(9) 0.0260(9) 0.0293(9) 0.0005(7) -0.0028(7) -0.0012(7) C7 0.0258(9) 0.0261(9) 0.0293(9) 0.0027(7) 0.0005(7) 0.0041(7) C8 0.0299(9) 0.0250(9) 0.0312(9) 0.0035(7) -0.0002(7) 0.0054(7) C9 0.0291(9) 0.0230(9) 0.0288(9) 0.0024(7) 0.0028(7) 0.0024(7) C10 0.0307(9) 0.0225(8) 0.0270(9) 0.0032(7) 0.0022(7) 0.0027(7) C11 0.0283(9) 0.0221(8) 0.0249(9) 0.0029(7) 0.0033(7) 0.0025(7) C12 0.0261(9) 0.0222(8) 0.0283(9) 0.0034(7) 0.0029(7) 0.0025(7) C13 0.0360(11) 0.0170(8) 0.0363(10) -0.0017(7) 0.0018(8) 0.0007(7) N2 0.0260(8) 0.0256(7) 0.0335(8) 0.0043(6) -0.0005(6) 0.0022(6) O3 0.0368(7) 0.0269(6) 0.0416(7) 0.0006(5) -0.0033(6) 0.0057(5) C14 0.0309(10) 0.0275(9) 0.0368(10) 0.0084(8) 0.0028(8) 0.0068(7) C15 0.0346(10) 0.0310(9) 0.0409(11) 0.0005(8) -0.0004(8) 0.0078(8) C16 0.0342(10) 0.0376(10) 0.0486(12) 0.0062(9) -0.0063(9) -0.0025(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 N1 C13 1.141(2) . ? O1 C1 1.3257(19) . ? O2 C1 1.2146(19) . ? C1 C2 1.485(2) . ? C2 C3 1.385(2) . ? C2 C7 1.391(2) . ? C3 C4 1.384(2) . ? C4 C5 1.400(2) . ? C5 C6 1.396(2) . ? C5 C8 1.463(2) . ? C6 C7 1.384(2) . ? C8 C9 1.340(2) . ? C9 C10 1.430(2) . ? C10 C11 1.355(2) . ? C11 C13 1.442(2) . ? C11 C12 1.446(2) . ? C12 C12 1.343(3) 2_735 ? N2 C14 1.320(2) . ? N2 C15 1.456(2) . ? N2 C16 1.459(2) . ? O3 C14 1.2429(19) . ? 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 O2 C1 O1 122.67(15) . . ? O2 C1 C2 122.70(16) . . ? O1 C1 C2 114.62(14) . . ? C3 C2 C7 119.15(14) . . ? C3 C2 C1 117.55(14) . . ? C7 C2 C1 123.28(15) . . ? C2 C3 C4 120.60(15) . . ? C3 C4 C5 120.74(16) . . ? C6 C5 C4 118.18(14) . . ? C6 C5 C8 123.93(14) . . ? C4 C5 C8 117.88(15) . . ? C7 C6 C5 120.83(14) . . ? C6 C7 C2 120.48(15) . . ? C9 C8 C5 127.77(16) . . ? C8 C9 C10 122.32(16) . . ? C11 C10 C9 126.34(16) . . ? C10 C11 C13 118.89(14) . . ? C10 C11 C12 123.86(15) . . ? C13 C11 C12 117.24(13) . . ? C12 C12 C11 125.32(19) 2_735 . ? N1 C13 C11 178.78(19) . . ? C14 N2 C15 120.84(14) . . ? C14 N2 C16 121.96(14) . . ? C15 N2 C16 117.19(13) . . ? O3 C14 N2 124.51(15) . . ? 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 O1 H1 O3 0.92(2) 1.71(2) 2.6314(16) 176(2) . _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 30.53 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.268 _refine_diff_density_min -0.218 _refine_diff_density_rms 0.047 # Attachment '- DPDC5.cif' data_DPDC5 _database_code_depnum_ccdc_archive 'CCDC 847950' #TrackingRef '- DPDC5.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H18 N2' _chemical_formula_weight 334.40 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 12.5981(9) _cell_length_b 6.0734(4) _cell_length_c 13.4724(9) _cell_angle_alpha 90.00 _cell_angle_beta 117.7370(10) _cell_angle_gamma 90.00 _cell_volume 912.37(11) _cell_formula_units_Z 2 _cell_measurement_temperature 125(2) _cell_measurement_reflns_used 4827 _cell_measurement_theta_min 3.03 _cell_measurement_theta_max 30.52 _exptl_crystal_description PLATE _exptl_crystal_colour YELLOW _exptl_crystal_size_max 0.17 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.217 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 352 _exptl_absorpt_coefficient_mu 0.072 _exptl_absorpt_correction_type EMPIRICAL _exptl_absorpt_correction_T_min 0.9879 _exptl_absorpt_correction_T_max 0.9971 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 125(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 13982 _diffrn_reflns_av_R_equivalents 0.0401 _diffrn_reflns_av_sigmaI/netI 0.0314 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.83 _diffrn_reflns_theta_max 30.56 _reflns_number_total 2791 _reflns_number_gt 2008 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0621P)^2^+0.1729P] 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 2791 _refine_ls_number_parameters 118 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0685 _refine_ls_R_factor_gt 0.0424 _refine_ls_wR_factor_ref 0.1236 _refine_ls_wR_factor_gt 0.1074 _refine_ls_goodness_of_fit_ref 1.019 _refine_ls_restrained_S_all 1.019 _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 N N 0.56363(11) 0.95488(18) 0.17542(10) 0.0336(3) Uani 1 1 d . . . C1 C 0.37756(10) 0.76609(18) 0.46844(9) 0.0214(2) Uani 1 1 d . . . H1A H 0.4139 0.8627 0.4376 0.026 Uiso 1 1 calc R . . C2 C 0.35981(10) 0.83539(19) 0.55745(10) 0.0237(2) Uani 1 1 d . . . H2A H 0.3846 0.9788 0.5875 0.028 Uiso 1 1 calc R . . C3 C 0.30610(10) 0.6974(2) 0.60330(9) 0.0245(3) Uani 1 1 d . . . H3A H 0.2944 0.7461 0.6645 0.029 Uiso 1 1 calc R . . C4 C 0.26957(11) 0.4881(2) 0.55921(10) 0.0249(3) Uani 1 1 d . . . H4A H 0.2320 0.3935 0.5896 0.030 Uiso 1 1 calc R . . C5 C 0.28821(10) 0.41751(18) 0.47048(9) 0.0217(2) Uani 1 1 d . . . H5A H 0.2637 0.2735 0.4412 0.026 Uiso 1 1 calc R . . C6 C 0.34242(9) 0.55445(17) 0.42333(9) 0.0182(2) Uani 1 1 d . . . C7 C 0.36024(10) 0.46830(18) 0.33102(9) 0.0196(2) Uani 1 1 d . . . H7A H 0.3317 0.3233 0.3067 0.023 Uiso 1 1 calc R . . C8 C 0.41250(10) 0.57106(18) 0.27643(9) 0.0196(2) Uani 1 1 d . . . H8A H 0.4417 0.7167 0.2978 0.024 Uiso 1 1 calc R . . C9 C 0.42549(10) 0.46750(18) 0.18701(9) 0.0193(2) Uani 1 1 d . . . H9A H 0.3975 0.3204 0.1686 0.023 Uiso 1 1 calc R . . C10 C 0.47456(10) 0.56219(17) 0.12623(9) 0.0186(2) Uani 1 1 d . . . C11 C 0.47998(9) 0.45255(17) 0.03341(9) 0.0190(2) Uani 1 1 d . . . H11A H 0.4536 0.3040 0.0185 0.023 Uiso 1 1 calc R . . C12 C 0.52329(10) 0.78152(19) 0.15414(10) 0.0225(2) 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 N 0.0492(7) 0.0269(5) 0.0339(6) -0.0090(4) 0.0271(6) -0.0093(5) C1 0.0234(5) 0.0206(5) 0.0219(5) 0.0000(4) 0.0120(4) -0.0004(4) C2 0.0259(6) 0.0221(5) 0.0228(6) -0.0041(4) 0.0110(5) 0.0017(4) C3 0.0232(5) 0.0324(6) 0.0199(5) -0.0023(4) 0.0118(4) 0.0045(5) C4 0.0246(6) 0.0319(6) 0.0229(6) 0.0014(5) 0.0151(5) -0.0015(5) C5 0.0229(5) 0.0224(5) 0.0218(5) -0.0016(4) 0.0121(4) -0.0033(4) C6 0.0180(5) 0.0205(5) 0.0172(5) -0.0003(4) 0.0091(4) 0.0004(4) C7 0.0212(5) 0.0207(5) 0.0183(5) -0.0015(4) 0.0104(4) 0.0001(4) C8 0.0217(5) 0.0203(5) 0.0183(5) -0.0008(4) 0.0107(4) 0.0006(4) C9 0.0214(5) 0.0196(5) 0.0186(5) -0.0004(4) 0.0108(4) 0.0008(4) C10 0.0201(5) 0.0195(5) 0.0175(5) -0.0015(4) 0.0098(4) 0.0005(4) C11 0.0206(5) 0.0190(5) 0.0186(5) -0.0024(4) 0.0102(4) -0.0009(4) C12 0.0282(6) 0.0240(5) 0.0203(5) -0.0025(4) 0.0155(5) -0.0004(4) _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 N C12 1.1461(15) . ? C1 C2 1.3837(15) . ? C1 C6 1.4025(15) . ? C2 C3 1.3895(16) . ? C3 C4 1.3877(17) . ? C4 C5 1.3890(16) . ? C5 C6 1.4019(15) . ? C6 C7 1.4597(14) . ? C7 C8 1.3471(15) . ? C8 C9 1.4343(14) . ? C9 C10 1.3618(15) . ? C10 C12 1.4415(15) . ? C10 C11 1.4461(14) . ? C11 C11 1.349(2) 3_665 ? 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 120.56(10) . . ? C1 C2 C3 120.69(11) . . ? C4 C3 C2 119.68(10) . . ? C3 C4 C5 119.74(11) . . ? C4 C5 C6 121.32(10) . . ? C5 C6 C1 118.00(10) . . ? C5 C6 C7 118.29(10) . . ? C1 C6 C7 123.71(10) . . ? C8 C7 C6 127.38(10) . . ? C7 C8 C9 122.09(10) . . ? C10 C9 C8 125.52(10) . . ? C9 C10 C12 119.39(10) . . ? C9 C10 C11 122.88(10) . . ? C12 C10 C11 117.73(9) . . ? C11 C11 C10 124.27(13) 3_665 . ? N C12 C10 178.57(12) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 30.56 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.377 _refine_diff_density_min -0.205 _refine_diff_density_rms 0.047 # Attachment '- DPDC7.cif' data_DPDC7 _database_code_depnum_ccdc_archive 'CCDC 847951' #TrackingRef '- DPDC7.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C29 H23 Cl2 N2' _chemical_formula_weight 470.39 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 Monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 22.398(3) _cell_length_b 11.1946(17) _cell_length_c 9.7652(14) _cell_angle_alpha 90.00 _cell_angle_beta 95.645(2) _cell_angle_gamma 90.00 _cell_volume 2436.6(6) _cell_formula_units_Z 4 _cell_measurement_temperature 125(2) _cell_measurement_reflns_used 2893 _cell_measurement_theta_min 2.86 _cell_measurement_theta_max 26.09 _exptl_crystal_description NEEDLE _exptl_crystal_colour PURPLE _exptl_crystal_size_max 0.56 _exptl_crystal_size_mid 0.03 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.282 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 980 _exptl_absorpt_coefficient_mu 0.286 _exptl_absorpt_correction_type EMPIRICAL _exptl_absorpt_correction_T_min 0.8562 _exptl_absorpt_correction_T_max 0.9943 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 125(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 19054 _diffrn_reflns_av_R_equivalents 0.1346 _diffrn_reflns_av_sigmaI/netI 0.1167 _diffrn_reflns_limit_h_min -31 _diffrn_reflns_limit_h_max 32 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.83 _diffrn_reflns_theta_max 30.53 _reflns_number_total 3720 _reflns_number_gt 1752 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0504P)^2^+0.6569P] 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 3720 _refine_ls_number_parameters 150 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1627 _refine_ls_R_factor_gt 0.0584 _refine_ls_wR_factor_ref 0.1423 _refine_ls_wR_factor_gt 0.1095 _refine_ls_goodness_of_fit_ref 1.009 _refine_ls_restrained_S_all 1.009 _refine_ls_shift/su_max 0.002 _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 N N 0.07507(10) 0.7683(2) 0.1893(2) 0.0361(6) Uani 1 1 d . . . C1 C 0.29408(13) 1.2222(2) 0.8565(3) 0.0361(7) Uani 1 1 d . . . H1A H 0.2745 1.2975 0.8469 0.043 Uiso 1 1 calc R . . C2 C 0.33763(13) 1.2037(2) 0.9662(3) 0.0384(7) Uani 1 1 d . . . H2A H 0.3477 1.2661 1.0303 0.046 Uiso 1 1 calc R . . C3 C 0.36597(12) 1.0954(2) 0.9815(3) 0.0304(6) Uani 1 1 d . . . H3A H 0.3958 1.0826 1.0561 0.037 Uiso 1 1 calc R . . C4 C 0.35102(11) 1.0047(2) 0.8884(3) 0.0312(6) Uani 1 1 d . . . H4A H 0.3705 0.9294 0.8994 0.037 Uiso 1 1 calc R . . C5 C 0.30766(11) 1.0234(2) 0.7787(3) 0.0264(6) Uani 1 1 d . . . H5A H 0.2978 0.9605 0.7152 0.032 Uiso 1 1 calc R . . C6 C 0.27855(10) 1.1327(2) 0.7604(2) 0.0225(5) Uani 1 1 d . . . C7 C 0.23320(11) 1.1578(2) 0.6453(2) 0.0249(6) Uani 1 1 d . . . H7A H 0.2181 1.2372 0.6395 0.030 Uiso 1 1 calc R . . C8 C 0.21055(11) 1.0822(2) 0.5475(2) 0.0234(5) Uani 1 1 d . . . H8A H 0.2245 1.0021 0.5508 0.028 Uiso 1 1 calc R . . C9 C 0.16626(11) 1.1157(2) 0.4377(2) 0.0253(6) Uani 1 1 d . . . H9A H 0.1555 1.1976 0.4293 0.030 Uiso 1 1 calc R . . C10 C 0.13888(10) 1.0381(2) 0.3456(2) 0.0248(6) Uani 1 1 d . . . H10A H 0.1501 0.9564 0.3527 0.030 Uiso 1 1 calc R . . C11 C 0.09403(11) 1.0719(2) 0.2382(2) 0.0257(6) Uani 1 1 d . . . H11A H 0.0866 1.1549 0.2257 0.031 Uiso 1 1 calc R . . C12 C 0.06110(11) 0.9959(2) 0.1523(2) 0.0240(5) Uani 1 1 d . . . C13 C 0.01710(10) 1.0358(2) 0.0431(2) 0.0265(6) Uani 1 1 d . . . H13A H 0.0120 1.1195 0.0314 0.032 Uiso 1 1 calc R . . C14 C 0.06893(11) 0.8688(3) 0.1720(2) 0.0258(6) Uani 1 1 d . . . Cl1 Cl 0.02719(3) 0.63383(6) -0.10791(8) 0.0417(2) Uani 1 1 d . . . C100 C 0.0000 0.5434(3) -0.2500 0.0380(10) Uani 1 2 d S . . H10C H -0.0318 0.4931 -0.2241 0.046 Uiso 0.50 1 d PR . . 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 N 0.0349(13) 0.0396(14) 0.0313(13) -0.0003(11) -0.0084(10) 0.0031(11) C1 0.0505(18) 0.0255(14) 0.0296(15) -0.0047(12) -0.0097(13) 0.0081(13) C2 0.0490(18) 0.0321(16) 0.0302(15) -0.0090(13) -0.0157(14) -0.0014(14) C3 0.0280(14) 0.0387(16) 0.0227(13) 0.0027(12) -0.0069(11) -0.0014(12) C4 0.0290(14) 0.0304(14) 0.0324(15) -0.0002(12) -0.0063(12) 0.0042(12) C5 0.0283(14) 0.0236(13) 0.0261(13) -0.0040(11) -0.0036(11) 0.0003(11) C6 0.0237(12) 0.0243(13) 0.0188(12) 0.0018(11) -0.0009(10) -0.0009(11) C7 0.0270(13) 0.0251(13) 0.0212(13) 0.0031(11) -0.0038(10) -0.0010(11) C8 0.0258(13) 0.0253(13) 0.0182(12) 0.0030(11) -0.0027(10) 0.0002(11) C9 0.0256(13) 0.0298(14) 0.0195(12) 0.0033(11) -0.0022(10) 0.0007(11) C10 0.0270(13) 0.0271(13) 0.0196(12) 0.0002(10) -0.0022(10) 0.0036(11) C11 0.0277(13) 0.0304(14) 0.0180(12) 0.0012(11) -0.0025(10) 0.0071(11) C12 0.0230(12) 0.0327(14) 0.0155(12) -0.0037(10) -0.0019(10) 0.0073(11) C13 0.0264(13) 0.0309(15) 0.0211(13) -0.0016(11) -0.0028(10) 0.0102(11) C14 0.0213(12) 0.0371(15) 0.0171(12) -0.0047(12) -0.0070(9) 0.0028(12) Cl1 0.0452(4) 0.0363(4) 0.0397(4) -0.0023(3) -0.0158(3) 0.0011(3) C100 0.046(2) 0.026(2) 0.038(2) 0.000 -0.0167(19) 0.000 _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 N C14 1.144(3) . ? C1 C2 1.391(3) . ? C1 C6 1.393(3) . ? C2 C3 1.370(4) . ? C3 C4 1.382(3) . ? C4 C5 1.389(3) . ? C5 C6 1.389(3) . ? C6 C7 1.466(3) . ? C7 C8 1.338(3) . ? C8 C9 1.437(3) . ? C9 C10 1.353(3) . ? C10 C11 1.430(3) . ? C11 C12 1.360(3) . ? C12 C14 1.444(4) . ? C12 C13 1.450(3) . ? C13 C13 1.345(5) 5_575 ? Cl1 C100 1.776(2) . ? C100 Cl1 1.776(2) 2_554 ? 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 121.4(2) . . ? C3 C2 C1 119.9(2) . . ? C2 C3 C4 119.9(2) . . ? C3 C4 C5 120.2(2) . . ? C4 C5 C6 121.0(2) . . ? C5 C6 C1 117.6(2) . . ? C5 C6 C7 123.3(2) . . ? C1 C6 C7 119.1(2) . . ? C8 C7 C6 127.7(2) . . ? C7 C8 C9 123.6(2) . . ? C10 C9 C8 124.3(2) . . ? C9 C10 C11 123.9(2) . . ? C12 C11 C10 125.9(2) . . ? C11 C12 C14 118.9(2) . . ? C11 C12 C13 123.3(2) . . ? C14 C12 C13 117.8(2) . . ? C13 C13 C12 125.5(3) 5_575 . ? N C14 C12 179.2(3) . . ? Cl1 C100 Cl1 110.5(2) . 2_554 ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 30.53 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.341 _refine_diff_density_min -0.352 _refine_diff_density_rms 0.070 # Attachment '- DPDC9.cif' data_DPDC9 _database_code_depnum_ccdc_archive 'CCDC 847952' #TrackingRef '- DPDC9.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C33 H28 Cl2 N2' _chemical_formula_weight 523.47 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 Monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 25.388(11) _cell_length_b 11.126(5) _cell_length_c 9.788(4) _cell_angle_alpha 90.00 _cell_angle_beta 94.187(7) _cell_angle_gamma 90.00 _cell_volume 2757(2) _cell_formula_units_Z 4 _cell_measurement_temperature 125(2) _cell_measurement_reflns_used 2010 _cell_measurement_theta_min 2.85 _cell_measurement_theta_max 30.55 _exptl_crystal_description NEEDLE _exptl_crystal_colour BLACK _exptl_crystal_size_max 0.59 _exptl_crystal_size_mid 0.02 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.261 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1096 _exptl_absorpt_coefficient_mu 0.260 _exptl_absorpt_correction_type EMPIRICAL _exptl_absorpt_correction_T_min 0.8617 _exptl_absorpt_correction_T_max 0.9974 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 125(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 11858 _diffrn_reflns_av_R_equivalents 0.2717 _diffrn_reflns_av_sigmaI/netI 0.2359 _diffrn_reflns_limit_h_min -31 _diffrn_reflns_limit_h_max 31 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 1.61 _diffrn_reflns_theta_max 26.37 _reflns_number_total 2830 _reflns_number_gt 1092 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0598P)^2^+4.8875P] 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 SHELXL _refine_ls_extinction_coef 0.0004(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2830 _refine_ls_number_parameters 169 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2301 _refine_ls_R_factor_gt 0.0843 _refine_ls_wR_factor_ref 0.2065 _refine_ls_wR_factor_gt 0.1597 _refine_ls_goodness_of_fit_ref 1.008 _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 N N 0.0659(2) -0.2327(5) 0.3396(5) 0.0376(14) Uani 1 1 d . . . C1 C 0.3252(2) 0.0248(5) -0.3511(6) 0.0297(16) Uani 1 1 d . . . H1A H 0.3152 -0.0366 -0.2907 0.036 Uiso 1 1 calc R . . C2 C 0.3625(2) 0.0009(5) -0.4410(7) 0.0358(17) Uani 1 1 d . . . H2A H 0.3782 -0.0766 -0.4418 0.043 Uiso 1 1 calc R . . C3 C 0.3781(2) 0.0890(5) -0.5322(6) 0.0334(16) Uani 1 1 d . . . H3A H 0.4043 0.0720 -0.5940 0.040 Uiso 1 1 calc R . . C4 C 0.3544(3) 0.2020(5) -0.5307(7) 0.0392(18) Uani 1 1 d . . . H4A H 0.3639 0.2626 -0.5927 0.047 Uiso 1 1 calc R . . C5 C 0.3172(3) 0.2251(5) -0.4390(6) 0.0383(18) Uani 1 1 d . . . H5A H 0.3017 0.3027 -0.4384 0.046 Uiso 1 1 calc R . . C6 C 0.3013(2) 0.1384(5) -0.3462(6) 0.0257(14) Uani 1 1 d . . . C7 C 0.2628(2) 0.1698(5) -0.2496(6) 0.0282(15) Uani 1 1 d . . . H7A H 0.2498 0.2498 -0.2559 0.034 Uiso 1 1 calc R . . C8 C 0.2431(2) 0.1021(5) -0.1534(6) 0.0260(15) Uani 1 1 d . . . H8A H 0.2545 0.0209 -0.1455 0.031 Uiso 1 1 calc R . . C9 C 0.2059(2) 0.1431(5) -0.0612(6) 0.0277(15) Uani 1 1 d . . . H9A H 0.1957 0.2252 -0.0671 0.033 Uiso 1 1 calc R . . C10 C 0.1841(2) 0.0754(5) 0.0330(6) 0.0284(15) Uani 1 1 d . . . H10A H 0.1949 -0.0063 0.0395 0.034 Uiso 1 1 calc R . . C11 C 0.1461(2) 0.1143(5) 0.1247(6) 0.0277(15) Uani 1 1 d . . . H11A H 0.1378 0.1975 0.1271 0.033 Uiso 1 1 calc R . . C12 C 0.1213(2) 0.0397(5) 0.2079(6) 0.0265(15) Uani 1 1 d . . . H12A H 0.1308 -0.0428 0.2062 0.032 Uiso 1 1 calc R . . C13 C 0.0825(2) 0.0732(5) 0.2977(6) 0.0270(15) Uani 1 1 d . . . H13A H 0.0761 0.1568 0.3067 0.032 Uiso 1 1 calc R . . C14 C 0.0535(2) -0.0011(5) 0.3720(6) 0.0293(15) Uani 1 1 d . . . C15 C 0.0148(2) 0.0368(5) 0.4646(6) 0.0269(15) Uani 1 1 d . . . H15A H 0.0099 0.1208 0.4761 0.032 Uiso 1 1 calc R . . C16 C 0.0602(2) -0.1310(6) 0.3527(6) 0.0315(15) Uani 1 1 d . . . Cl Cl 0.02368(7) 0.36863(15) 0.11900(19) 0.0467(6) Uani 1 1 d . . . C17 C 0.0000 0.4569(8) 0.2500 0.048(3) Uani 1 2 d S . . H17A H -0.0280 0.5076 0.2120 0.057 Uiso 1 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 N 0.038(3) 0.024(3) 0.051(4) 0.004(3) 0.007(3) 0.005(3) C1 0.041(4) 0.016(3) 0.033(4) -0.002(3) 0.012(3) 0.003(3) C2 0.037(4) 0.025(4) 0.045(4) 0.001(3) 0.002(3) 0.005(3) C3 0.035(4) 0.027(3) 0.039(4) -0.003(3) 0.008(3) 0.000(3) C4 0.051(5) 0.025(4) 0.044(4) 0.003(3) 0.020(4) -0.002(3) C5 0.050(5) 0.021(3) 0.046(4) 0.000(3) 0.015(4) 0.002(3) C6 0.025(3) 0.018(3) 0.034(4) -0.006(3) -0.002(3) -0.008(3) C7 0.039(4) 0.015(3) 0.032(4) -0.003(3) 0.010(3) 0.000(3) C8 0.026(4) 0.024(3) 0.028(4) -0.009(3) 0.001(3) -0.006(3) C9 0.034(4) 0.021(3) 0.028(3) -0.002(3) 0.000(3) -0.003(3) C10 0.032(4) 0.024(3) 0.030(4) -0.002(3) 0.007(3) 0.002(3) C11 0.033(4) 0.020(3) 0.031(4) 0.000(3) 0.004(3) -0.001(3) C12 0.028(4) 0.019(3) 0.032(4) 0.003(3) -0.003(3) 0.001(3) C13 0.030(4) 0.023(3) 0.027(3) 0.003(3) -0.001(3) 0.009(3) C14 0.036(4) 0.025(3) 0.026(3) 0.008(3) -0.004(3) 0.007(3) C15 0.026(4) 0.024(3) 0.031(4) 0.000(3) 0.002(3) 0.008(3) C16 0.028(4) 0.033(4) 0.034(4) 0.008(3) 0.007(3) 0.001(3) Cl 0.0572(12) 0.0266(8) 0.0581(12) -0.0016(9) 0.0174(9) 0.0010(9) C17 0.059(7) 0.029(5) 0.058(7) 0.000 0.020(6) 0.000 _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 N C16 1.149(7) . ? C1 C2 1.366(8) . ? C1 C6 1.404(7) . ? C2 C3 1.401(8) . ? C3 C4 1.394(8) . ? C4 C5 1.372(8) . ? C5 C6 1.405(8) . ? C6 C7 1.451(8) . ? C7 C8 1.332(7) . ? C8 C9 1.428(7) . ? C9 C10 1.340(7) . ? C10 C11 1.432(7) . ? C11 C12 1.350(7) . ? C12 C13 1.418(8) . ? C13 C14 1.354(8) . ? C14 C15 1.447(8) . ? C14 C16 1.470(9) . ? C15 C15 1.337(11) 5_556 ? Cl C17 1.756(5) . ? C17 Cl 1.756(5) 2 ? 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 121.3(6) . . ? C1 C2 C3 121.0(6) . . ? C4 C3 C2 118.9(6) . . ? C5 C4 C3 119.5(6) . . ? C4 C5 C6 122.6(6) . . ? C1 C6 C5 116.7(5) . . ? C1 C6 C7 123.5(5) . . ? C5 C6 C7 119.7(5) . . ? C8 C7 C6 129.1(5) . . ? C7 C8 C9 124.5(5) . . ? C10 C9 C8 125.4(6) . . ? C9 C10 C11 126.2(6) . . ? C12 C11 C10 123.8(6) . . ? C11 C12 C13 126.0(5) . . ? C14 C13 C12 127.1(5) . . ? C13 C14 C15 125.4(5) . . ? C13 C14 C16 117.2(5) . . ? C15 C14 C16 117.3(5) . . ? C15 C15 C14 125.3(7) 5_556 . ? N C16 C14 178.9(7) . . ? Cl C17 Cl 112.0(5) . 2 ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 26.37 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.565 _refine_diff_density_min -0.388 _refine_diff_density_rms 0.086