# Electronic Supplementary Material (ESI) for Photochemical & Photobiological Science # This journal is © The Royal Society of Chemistry and Owner Societies 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_ic15008 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H16 N2' _chemical_formula_weight 308.37 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting 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 9.0125(3) _cell_length_b 11.4927(4) _cell_length_c 16.4078(6) _cell_angle_alpha 90.00 _cell_angle_beta 103.974(3) _cell_angle_gamma 90.00 _cell_volume 1649.19(10) _cell_formula_units_Z 4 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.242 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 648 _exptl_absorpt_coefficient_mu 0.566 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'multiwire proportional' _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 5908 _diffrn_reflns_av_R_equivalents 0.0172 _diffrn_reflns_av_sigmaI/netI 0.0204 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 4.75 _diffrn_reflns_theta_max 67.98 _reflns_number_total 3005 _reflns_number_gt 2712 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker FRAMBO' _computing_cell_refinement 'Bruker FRAMBO' _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^)+(0.1280P)^2^+0.8801P] 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 0.0068(10) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3005 _refine_ls_number_parameters 218 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0637 _refine_ls_R_factor_gt 0.0593 _refine_ls_wR_factor_ref 0.1960 _refine_ls_wR_factor_gt 0.1890 _refine_ls_goodness_of_fit_ref 0.990 _refine_ls_restrained_S_all 0.990 _refine_ls_shift/su_max 0.003 _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 1.1620(3) 0.8390(2) 0.41813(14) 0.0610(6) Uani 1 1 d . . . N2 N 0.8265(2) 0.55281(17) 0.16103(11) 0.0472(5) Uani 1 1 d . . . H2A H 0.8460 0.5574 0.1123 0.057 Uiso 1 1 calc R . . C1 C 1.0779(2) 0.76652(18) 0.35171(12) 0.0384(5) Uani 1 1 d . . . C2 C 0.9864(2) 0.67582(19) 0.37000(13) 0.0442(5) Uani 1 1 d . . . H2B H 0.9823 0.6629 0.4254 0.053 Uiso 1 1 calc R . . C3 C 0.9035(2) 0.60627(19) 0.30793(13) 0.0427(5) Uani 1 1 d . . . H3A H 0.8441 0.5468 0.3218 0.051 Uiso 1 1 calc R . . C4 C 0.9063(2) 0.62298(17) 0.22301(12) 0.0367(5) Uani 1 1 d . . . C5 C 0.9972(2) 0.71434(17) 0.20494(11) 0.0350(5) Uani 1 1 d . . . C6 C 1.0812(2) 0.78470(17) 0.26801(12) 0.0358(5) Uani 1 1 d . . . C7 C 1.1704(2) 0.88012(17) 0.23585(12) 0.0380(5) Uani 1 1 d . . . H7A H 1.2295 0.9295 0.2808 0.046 Uiso 1 1 calc R . . C8 C 1.2694(2) 0.81799(17) 0.18641(13) 0.0389(5) Uani 1 1 d . . . C9 C 1.4256(3) 0.8287(2) 0.19833(16) 0.0498(6) Uani 1 1 d . . . H9A H 1.4811 0.8773 0.2400 0.060 Uiso 1 1 calc R . . C10 C 1.4987(3) 0.7658(3) 0.14707(19) 0.0621(7) Uani 1 1 d . . . H10A H 1.6039 0.7726 0.1543 0.075 Uiso 1 1 calc R . . C11 C 1.4163(3) 0.6934(2) 0.08562(18) 0.0603(7) Uani 1 1 d . . . H11A H 1.4666 0.6513 0.0520 0.072 Uiso 1 1 calc R . . C12 C 1.2589(3) 0.68253(19) 0.07326(15) 0.0477(6) Uani 1 1 d . . . H12A H 1.2038 0.6332 0.0319 0.057 Uiso 1 1 calc R . . C13 C 1.1854(2) 0.74622(17) 0.12333(12) 0.0374(5) Uani 1 1 d . . . C14 C 1.0145(2) 0.74907(17) 0.11788(12) 0.0364(5) Uani 1 1 d . . . H14A H 0.9554 0.6994 0.0731 0.044 Uiso 1 1 calc R . . C15 C 0.9670(2) 0.87723(18) 0.10749(12) 0.0370(5) Uani 1 1 d . . . C16 C 0.8555(2) 0.9244(2) 0.04342(13) 0.0447(5) Uani 1 1 d . . . H16A H 0.7981 0.8771 0.0015 0.054 Uiso 1 1 calc R . . C17 C 0.8301(3) 1.0443(2) 0.04245(15) 0.0530(6) Uani 1 1 d . . . H17A H 0.7545 1.0772 -0.0001 0.064 Uiso 1 1 calc R . . C18 C 0.9164(3) 1.1137(2) 0.10412(16) 0.0552(6) Uani 1 1 d . . . H18A H 0.8996 1.1936 0.1024 0.066 Uiso 1 1 calc R . . C19 C 1.0284(3) 1.0667(2) 0.16901(15) 0.0488(6) Uani 1 1 d . . . H19A H 1.0862 1.1143 0.2106 0.059 Uiso 1 1 calc R . . C20 C 1.0527(2) 0.94778(18) 0.17066(12) 0.0385(5) Uani 1 1 d . . . C21 C 1.2267(3) 0.89613(19) 0.47187(12) 0.0488(6) Uani 1 1 d . . . C22 C 0.7109(3) 0.4708(2) 0.17187(16) 0.0527(6) Uani 1 1 d . . . H22A H 0.6701 0.4310 0.1198 0.079 Uiso 1 1 calc R . . H22B H 0.6302 0.5117 0.1886 0.079 Uiso 1 1 calc R . . H22C H 0.7558 0.4152 0.2144 0.079 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 0.0712(14) 0.0597(13) 0.0534(12) 0.0149(10) 0.0175(10) 0.0129(11) N2 0.0502(10) 0.0495(11) 0.0419(9) -0.0018(8) 0.0114(8) -0.0158(8) C1 0.0428(11) 0.0405(10) 0.0305(10) 0.0003(8) 0.0061(8) 0.0054(8) C2 0.0517(12) 0.0493(12) 0.0343(10) 0.0068(9) 0.0154(9) 0.0042(9) C3 0.0470(11) 0.0430(11) 0.0418(11) 0.0055(9) 0.0177(9) -0.0021(8) C4 0.0345(9) 0.0376(10) 0.0387(10) 0.0039(8) 0.0098(8) 0.0023(7) C5 0.0376(10) 0.0365(10) 0.0312(9) 0.0013(7) 0.0088(7) 0.0008(7) C6 0.0364(10) 0.0352(10) 0.0362(10) 0.0019(8) 0.0096(8) 0.0029(7) C7 0.0425(10) 0.0362(10) 0.0348(10) -0.0025(8) 0.0084(8) -0.0049(8) C8 0.0415(11) 0.0342(10) 0.0421(10) 0.0069(8) 0.0123(8) 0.0002(8) C9 0.0415(11) 0.0473(12) 0.0607(14) 0.0085(10) 0.0124(10) -0.0033(9) C10 0.0427(12) 0.0638(16) 0.0858(19) 0.0152(14) 0.0272(12) 0.0082(11) C11 0.0667(16) 0.0564(14) 0.0686(16) 0.0117(12) 0.0372(13) 0.0202(12) C12 0.0622(14) 0.0388(11) 0.0473(12) 0.0042(9) 0.0235(10) 0.0074(9) C13 0.0450(11) 0.0327(9) 0.0370(10) 0.0059(8) 0.0144(8) 0.0017(8) C14 0.0422(10) 0.0359(10) 0.0315(9) 0.0001(7) 0.0097(7) -0.0039(8) C15 0.0402(10) 0.0392(10) 0.0350(10) 0.0037(8) 0.0155(8) 0.0011(8) C16 0.0428(11) 0.0549(13) 0.0386(10) 0.0084(9) 0.0143(8) 0.0024(9) C17 0.0516(13) 0.0603(14) 0.0520(13) 0.0207(11) 0.0220(10) 0.0162(11) C18 0.0697(15) 0.0410(12) 0.0636(15) 0.0131(10) 0.0333(12) 0.0163(11) C19 0.0627(14) 0.0381(11) 0.0518(12) -0.0024(9) 0.0262(10) 0.0008(10) C20 0.0442(11) 0.0376(10) 0.0375(10) 0.0025(8) 0.0171(8) 0.0017(8) C21 0.0699(15) 0.0434(12) 0.0235(9) -0.0082(8) -0.0076(9) -0.0056(10) C22 0.0441(12) 0.0521(13) 0.0593(14) 0.0041(11) 0.0072(10) -0.0124(10) _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 C21 1.140(3) . ? N1 C1 1.434(3) . ? N2 C4 1.360(3) . ? N2 C22 1.448(3) . ? C1 C6 1.397(3) . ? C1 C2 1.406(3) . ? C2 C3 1.367(3) . ? C3 C4 1.413(3) . ? C4 C5 1.407(3) . ? C5 C6 1.386(3) . ? C5 C14 1.527(3) . ? C6 C7 1.527(3) . ? C7 C8 1.521(3) . ? C7 C20 1.526(3) . ? C8 C9 1.379(3) . ? C8 C13 1.395(3) . ? C9 C10 1.390(4) . ? C10 C11 1.378(4) . ? C11 C12 1.390(4) . ? C12 C13 1.383(3) . ? C13 C14 1.522(3) . ? C14 C15 1.532(3) . ? C15 C16 1.378(3) . ? C15 C20 1.393(3) . ? C16 C17 1.397(4) . ? C17 C18 1.373(4) . ? C18 C19 1.387(3) . ? C19 C20 1.383(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C21 N1 C1 178.6(3) . . ? C4 N2 C22 124.10(19) . . ? C6 C1 C2 118.29(19) . . ? C6 C1 N1 121.84(19) . . ? C2 C1 N1 119.86(18) . . ? C3 C2 C1 121.20(18) . . ? C2 C3 C4 121.25(19) . . ? N2 C4 C5 120.97(17) . . ? N2 C4 C3 121.67(18) . . ? C5 C4 C3 117.35(18) . . ? C6 C5 C4 121.28(17) . . ? C6 C5 C14 112.67(17) . . ? C4 C5 C14 126.05(17) . . ? C5 C6 C1 120.63(18) . . ? C5 C6 C7 113.54(16) . . ? C1 C6 C7 125.82(18) . . ? C8 C7 C20 105.29(15) . . ? C8 C7 C6 105.83(16) . . ? C20 C7 C6 105.84(15) . . ? C9 C8 C13 120.7(2) . . ? C9 C8 C7 126.3(2) . . ? C13 C8 C7 112.94(17) . . ? C8 C9 C10 119.0(2) . . ? C11 C10 C9 120.4(2) . . ? C10 C11 C12 120.8(2) . . ? C13 C12 C11 119.0(2) . . ? C12 C13 C8 120.1(2) . . ? C12 C13 C14 126.8(2) . . ? C8 C13 C14 113.05(17) . . ? C13 C14 C5 105.65(15) . . ? C13 C14 C15 106.19(16) . . ? C5 C14 C15 105.46(15) . . ? C16 C15 C20 120.65(19) . . ? C16 C15 C14 126.56(19) . . ? C20 C15 C14 112.77(17) . . ? C15 C16 C17 119.0(2) . . ? C18 C17 C16 120.2(2) . . ? C17 C18 C19 121.2(2) . . ? C20 C19 C18 118.8(2) . . ? C19 C20 C15 120.3(2) . . ? C19 C20 C7 126.7(2) . . ? C15 C20 C7 113.06(17) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 67.98 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.558 _refine_diff_density_min -0.491 _refine_diff_density_rms 0.052 _database_code_depnum_ccdc_archive 'CCDC 945642' ####################################################################### # # 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_ic16170 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C39 H30 N2 O' _chemical_formula_weight 542.65 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 '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 11.0230(2) _cell_length_b 15.0169(3) _cell_length_c 17.9072(3) _cell_angle_alpha 90.00 _cell_angle_beta 101.637(2) _cell_angle_gamma 90.00 _cell_volume 2903.27(9) _cell_formula_units_Z 4 _cell_measurement_temperature 250(2) _cell_measurement_reflns_used 4335 _cell_measurement_theta_min 3.8550 _cell_measurement_theta_max 74.3440 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.241 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1144 _exptl_absorpt_coefficient_mu 0.575 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.95408 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 250(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Oxford Diffraction Gemini A' _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10896 _diffrn_reflns_av_R_equivalents 0.0294 _diffrn_reflns_av_sigmaI/netI 0.0433 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 3.88 _diffrn_reflns_theta_max 67.99 _reflns_number_total 5280 _reflns_number_gt 4293 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXTL _computing_publication_material 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^)+(0.0857P)^2^+0.7136P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5280 _refine_ls_number_parameters 380 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0625 _refine_ls_R_factor_gt 0.0506 _refine_ls_wR_factor_ref 0.1562 _refine_ls_wR_factor_gt 0.1374 _refine_ls_goodness_of_fit_ref 0.960 _refine_ls_restrained_S_all 0.960 _refine_ls_shift/su_max 0.006 _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 0.53044(15) 0.07177(11) 0.14785(10) 0.0480(4) Uani 1 1 d . . . H1A H 0.5518 0.0603 0.1046 0.058 Uiso 1 1 calc R . . N2 N 0.02430(15) 0.33228(11) 0.14406(10) 0.0491(4) Uani 1 1 d . . . C1 C 0.42618(15) 0.12288(11) 0.14634(9) 0.0349(3) Uani 1 1 d . . . C2 C 0.40279(15) 0.19722(11) 0.09739(10) 0.0361(4) Uani 1 1 d . . . C3 C 0.29874(15) 0.25043(10) 0.09326(9) 0.0344(3) Uani 1 1 d . . . C4 C 0.21411(15) 0.23277(10) 0.14006(9) 0.0323(3) Uani 1 1 d . . . C5 C 0.23530(14) 0.15920(11) 0.18853(9) 0.0323(3) Uani 1 1 d . . . C6 C 0.33735(15) 0.10373(10) 0.19066(9) 0.0325(3) Uani 1 1 d . . . C7 C 0.48874(16) 0.23141(12) 0.04625(10) 0.0403(4) Uani 1 1 d . . . H7A H 0.5637 0.1942 0.0491 0.048 Uiso 1 1 calc R . . C8 C 0.41038(17) 0.23711(11) -0.03404(10) 0.0399(4) Uani 1 1 d . . . C9 C 0.4358(2) 0.19830(13) -0.09918(12) 0.0502(5) Uani 1 1 d . . . H9A H 0.5061 0.1620 -0.0964 0.060 Uiso 1 1 calc R . . C10 C 0.3561(2) 0.21351(15) -0.16907(12) 0.0589(6) Uani 1 1 d . . . H10A H 0.3740 0.1886 -0.2138 0.071 Uiso 1 1 calc R . . C11 C 0.2516(2) 0.26471(14) -0.17306(12) 0.0578(5) Uani 1 1 d . . . H11A H 0.1981 0.2740 -0.2204 0.069 Uiso 1 1 calc R . . C12 C 0.2243(2) 0.30289(13) -0.10737(11) 0.0481(4) Uani 1 1 d . . . H12A H 0.1524 0.3374 -0.1101 0.058 Uiso 1 1 calc R . . C13 C 0.30410(17) 0.28942(11) -0.03847(10) 0.0395(4) Uani 1 1 d . . . C14 C 0.29357(17) 0.32902(11) 0.03860(10) 0.0379(4) Uani 1 1 d . . . H14A H 0.2187 0.3663 0.0359 0.045 Uiso 1 1 calc R . . C15 C 0.41365(17) 0.38033(12) 0.06620(10) 0.0401(4) Uani 1 1 d . . . C16 C 0.4231(2) 0.47026(13) 0.08372(11) 0.0482(5) Uani 1 1 d . . . H16A H 0.3518 0.5057 0.0796 0.058 Uiso 1 1 calc R . . C17 C 0.5403(2) 0.50687(15) 0.10747(12) 0.0599(6) Uani 1 1 d . . . H17A H 0.5485 0.5679 0.1189 0.072 Uiso 1 1 calc R . . C18 C 0.6446(2) 0.45445(17) 0.11441(12) 0.0629(6) Uani 1 1 d . . . H18A H 0.7232 0.4801 0.1312 0.075 Uiso 1 1 calc R . . C19 C 0.6351(2) 0.36364(16) 0.09672(11) 0.0532(5) Uani 1 1 d . . . H19A H 0.7063 0.3279 0.1020 0.064 Uiso 1 1 calc R . . C20 C 0.51859(18) 0.32768(12) 0.07138(10) 0.0419(4) Uani 1 1 d . . . C21 C 0.33725(15) 0.02509(11) 0.24571(9) 0.0348(3) Uani 1 1 d . . . H21A H 0.4074 -0.0163 0.2464 0.042 Uiso 1 1 calc RD . . C22 C 0.33952(16) 0.06844(11) 0.32278(9) 0.0362(4) Uani 1 1 d . . . C23 C 0.42734(17) 0.05514(12) 0.38892(10) 0.0426(4) Uani 1 1 d . . . H23A H 0.4926 0.0146 0.3898 0.051 Uiso 1 1 calc R . . C24 C 0.4174(2) 0.10270(14) 0.45407(11) 0.0511(5) Uani 1 1 d . . . H24A H 0.4769 0.0947 0.4992 0.061 Uiso 1 1 calc R . . C25 C 0.3209(2) 0.16152(14) 0.45308(11) 0.0523(5) Uani 1 1 d . . . H25A H 0.3154 0.1933 0.4975 0.063 Uiso 1 1 calc R . . C26 C 0.23158(19) 0.17432(12) 0.38680(11) 0.0446(4) Uani 1 1 d . . . H26A H 0.1659 0.2144 0.3862 0.053 Uiso 1 1 calc R . . C27 C 0.24112(16) 0.12722(11) 0.32202(9) 0.0360(4) Uani 1 1 d . . . C28 C 0.15345(15) 0.13240(11) 0.24436(10) 0.0359(4) Uani 1 1 d . . . H28A H 0.0831 0.1736 0.2437 0.043 Uiso 1 1 calc R . . C29 C 0.11257(16) 0.03697(12) 0.22346(9) 0.0379(4) Uani 1 1 d . . . C30 C -0.00742(18) 0.00549(15) 0.20751(11) 0.0490(5) Uani 1 1 d . . . H30A H -0.0744 0.0442 0.2075 0.059 Uiso 1 1 calc R . . C31 C -0.0277(2) -0.08486(17) 0.19138(13) 0.0632(6) Uani 1 1 d . . . H31A H -0.1090 -0.1071 0.1805 0.076 Uiso 1 1 calc R . . C32 C 0.0701(2) -0.14163(15) 0.19120(13) 0.0606(6) Uani 1 1 d . . . H32A H 0.0548 -0.2023 0.1801 0.073 Uiso 1 1 calc R . . C33 C 0.1917(2) -0.11019(13) 0.20732(11) 0.0480(4) Uani 1 1 d . . . H33A H 0.2585 -0.1490 0.2072 0.058 Uiso 1 1 calc R . . C34 C 0.21179(17) -0.02045(11) 0.22359(9) 0.0373(4) Uani 1 1 d . . . C35 C 0.10931(15) 0.28911(11) 0.14085(9) 0.0348(4) Uani 1 1 d . . . C36 C 0.6066(2) 0.03603(17) 0.21640(14) 0.0610(6) Uani 1 1 d . . . H36A H 0.6932 0.0459 0.2154 0.092 Uiso 1 1 calc R . . H36B H 0.5914 -0.0274 0.2193 0.092 Uiso 1 1 calc RD . . H36C H 0.5864 0.0655 0.2605 0.092 Uiso 1 1 calc R . . O1 O 0.75460(17) 0.12219(15) 0.07947(13) 0.0842(6) Uani 1 1 d . . . C37 C 0.7537(3) -0.0055(3) 0.0029(3) 0.1126(14) Uani 1 1 d . . . H37A H 0.6745 -0.0168 0.0168 0.169 Uiso 1 1 calc R . . H37B H 0.8106 -0.0535 0.0217 0.169 Uiso 1 1 calc R . . H37C H 0.7425 -0.0019 -0.0521 0.169 Uiso 1 1 calc R . . C38 C 0.8051(2) 0.07993(17) 0.03731(13) 0.0564(5) Uani 1 1 d . . . C39 C 0.9269(2) 0.10940(19) 0.02208(16) 0.0692(6) Uani 1 1 d . . . H39A H 0.9495 0.1661 0.0471 0.104 Uiso 1 1 calc R . . H39B H 0.9208 0.1160 -0.0324 0.104 Uiso 1 1 calc R . . H39C H 0.9895 0.0653 0.0417 0.104 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 0.0442(8) 0.0545(9) 0.0489(9) 0.0072(7) 0.0177(7) 0.0175(7) N2 0.0430(9) 0.0471(9) 0.0589(10) 0.0079(7) 0.0141(7) 0.0121(7) C1 0.0353(8) 0.0316(7) 0.0387(8) -0.0004(6) 0.0095(6) 0.0015(6) C2 0.0356(8) 0.0346(8) 0.0410(8) 0.0025(7) 0.0144(7) 0.0009(7) C3 0.0355(8) 0.0316(8) 0.0372(8) 0.0027(6) 0.0102(6) -0.0004(6) C4 0.0321(7) 0.0305(7) 0.0349(8) 0.0016(6) 0.0083(6) 0.0005(6) C5 0.0321(8) 0.0320(7) 0.0334(8) 0.0008(6) 0.0081(6) -0.0012(6) C6 0.0345(8) 0.0301(7) 0.0326(7) 0.0010(6) 0.0058(6) 0.0003(6) C7 0.0385(8) 0.0397(9) 0.0471(9) 0.0044(7) 0.0191(7) 0.0008(7) C8 0.0468(9) 0.0322(8) 0.0451(9) 0.0029(7) 0.0200(7) -0.0071(7) C9 0.0612(12) 0.0385(9) 0.0577(11) -0.0053(8) 0.0280(9) -0.0071(8) C10 0.0853(16) 0.0498(11) 0.0458(11) -0.0114(9) 0.0229(10) -0.0168(11) C11 0.0757(14) 0.0516(11) 0.0442(10) -0.0006(9) 0.0075(9) -0.0119(11) C12 0.0542(11) 0.0411(9) 0.0488(10) 0.0063(8) 0.0098(8) -0.0067(8) C13 0.0464(9) 0.0327(8) 0.0422(9) 0.0052(7) 0.0157(7) -0.0059(7) C14 0.0418(9) 0.0330(8) 0.0420(9) 0.0068(7) 0.0162(7) 0.0035(7) C15 0.0503(10) 0.0390(9) 0.0354(8) 0.0025(7) 0.0188(7) -0.0027(7) C16 0.0688(12) 0.0400(9) 0.0416(9) -0.0014(7) 0.0248(9) -0.0057(9) C17 0.0860(16) 0.0510(11) 0.0486(11) -0.0112(9) 0.0279(11) -0.0228(11) C18 0.0696(14) 0.0753(15) 0.0470(11) -0.0124(10) 0.0196(10) -0.0350(13) C19 0.0493(11) 0.0687(13) 0.0454(10) -0.0012(9) 0.0182(8) -0.0126(10) C20 0.0480(10) 0.0442(9) 0.0379(9) 0.0013(7) 0.0188(7) -0.0070(8) C21 0.0379(8) 0.0298(7) 0.0360(8) 0.0035(6) 0.0061(6) 0.0020(6) C22 0.0427(9) 0.0303(8) 0.0357(8) 0.0036(6) 0.0078(7) -0.0068(6) C23 0.0441(9) 0.0406(9) 0.0407(9) 0.0057(7) 0.0028(7) -0.0075(7) C24 0.0614(12) 0.0534(11) 0.0356(9) 0.0021(8) 0.0024(8) -0.0169(9) C25 0.0732(13) 0.0491(10) 0.0377(9) -0.0065(8) 0.0187(9) -0.0171(10) C26 0.0564(11) 0.0359(9) 0.0470(10) 0.0002(7) 0.0238(8) -0.0072(8) C27 0.0411(8) 0.0327(8) 0.0362(8) 0.0052(6) 0.0129(7) -0.0066(7) C28 0.0347(8) 0.0358(8) 0.0395(8) 0.0058(7) 0.0129(6) 0.0014(6) C29 0.0403(9) 0.0414(9) 0.0317(8) 0.0080(7) 0.0064(6) -0.0061(7) C30 0.0414(9) 0.0583(11) 0.0461(10) 0.0112(9) 0.0058(8) -0.0095(8) C31 0.0556(13) 0.0693(14) 0.0603(13) 0.0068(11) 0.0016(10) -0.0299(11) C32 0.0749(15) 0.0461(11) 0.0564(12) 0.0004(9) 0.0028(10) -0.0239(11) C33 0.0637(12) 0.0373(9) 0.0410(9) 0.0017(7) 0.0053(8) -0.0077(8) C34 0.0451(9) 0.0355(8) 0.0303(8) 0.0053(6) 0.0053(6) -0.0061(7) C35 0.0368(8) 0.0345(8) 0.0335(8) 0.0059(6) 0.0080(6) -0.0006(7) C36 0.0428(10) 0.0720(14) 0.0660(13) 0.0076(11) 0.0056(9) 0.0158(10) O1 0.0601(10) 0.0955(14) 0.1022(15) -0.0103(12) 0.0287(10) 0.0206(10) C37 0.084(2) 0.132(3) 0.122(3) -0.046(3) 0.021(2) -0.035(2) C38 0.0444(10) 0.0695(13) 0.0540(11) 0.0023(10) 0.0069(9) 0.0107(10) C39 0.0638(14) 0.0711(15) 0.0768(16) 0.0031(12) 0.0239(12) 0.0066(12) _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 C1 1.378(2) . ? N1 C36 1.444(3) . ? N2 C35 1.150(2) . ? C1 C6 1.409(2) . ? C1 C2 1.411(2) . ? C2 C3 1.387(2) . ? C2 C7 1.533(2) . ? C3 C4 1.399(2) . ? C3 C14 1.527(2) . ? C4 C5 1.395(2) . ? C4 C35 1.434(2) . ? C5 C6 1.394(2) . ? C5 C28 1.529(2) . ? C6 C21 1.538(2) . ? C7 C8 1.523(3) . ? C7 C20 1.530(3) . ? C8 C9 1.383(3) . ? C8 C13 1.399(3) . ? C9 C10 1.395(3) . ? C10 C11 1.375(4) . ? C11 C12 1.395(3) . ? C12 C13 1.378(3) . ? C13 C14 1.528(2) . ? C14 C15 1.525(3) . ? C15 C16 1.386(3) . ? C15 C20 1.389(3) . ? C16 C17 1.389(3) . ? C17 C18 1.378(4) . ? C18 C19 1.399(3) . ? C19 C20 1.383(3) . ? C21 C22 1.521(2) . ? C21 C34 1.522(2) . ? C22 C23 1.385(3) . ? C22 C27 1.396(2) . ? C23 C24 1.391(3) . ? C24 C25 1.379(3) . ? C25 C26 1.394(3) . ? C26 C27 1.381(3) . ? C27 C28 1.527(2) . ? C28 C29 1.526(2) . ? C29 C30 1.379(3) . ? C29 C34 1.392(3) . ? C30 C31 1.396(3) . ? C31 C32 1.374(4) . ? C32 C33 1.395(3) . ? C33 C34 1.387(3) . ? O1 C38 1.205(3) . ? C37 C38 1.484(4) . ? C38 C39 1.490(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 N1 C36 124.30(16) . . ? N1 C1 C6 123.16(15) . . ? N1 C1 C2 120.02(15) . . ? C6 C1 C2 116.80(15) . . ? C3 C2 C1 122.31(14) . . ? C3 C2 C7 112.27(14) . . ? C1 C2 C7 125.36(15) . . ? C2 C3 C4 120.17(15) . . ? C2 C3 C14 113.77(14) . . ? C4 C3 C14 125.95(15) . . ? C5 C4 C3 118.32(15) . . ? C5 C4 C35 119.67(14) . . ? C3 C4 C35 121.98(14) . . ? C6 C5 C4 121.54(14) . . ? C6 C5 C28 113.83(14) . . ? C4 C5 C28 124.62(14) . . ? C5 C6 C1 120.75(14) . . ? C5 C6 C21 111.79(14) . . ? C1 C6 C21 127.45(14) . . ? C8 C7 C20 105.78(14) . . ? C8 C7 C2 106.35(14) . . ? C20 C7 C2 105.24(14) . . ? C9 C8 C13 119.93(18) . . ? C9 C8 C7 126.85(18) . . ? C13 C8 C7 113.21(15) . . ? C8 C9 C10 119.3(2) . . ? C11 C10 C9 120.51(19) . . ? C10 C11 C12 120.4(2) . . ? C13 C12 C11 119.2(2) . . ? C12 C13 C8 120.59(17) . . ? C12 C13 C14 126.90(17) . . ? C8 C13 C14 112.48(16) . . ? C15 C14 C3 105.37(14) . . ? C15 C14 C13 105.67(13) . . ? C3 C14 C13 106.16(13) . . ? C16 C15 C20 121.06(18) . . ? C16 C15 C14 125.93(18) . . ? C20 C15 C14 113.00(15) . . ? C15 C16 C17 118.6(2) . . ? C18 C17 C16 120.59(19) . . ? C17 C18 C19 120.9(2) . . ? C20 C19 C18 118.5(2) . . ? C19 C20 C15 120.38(18) . . ? C19 C20 C7 126.57(18) . . ? C15 C20 C7 113.05(16) . . ? C22 C21 C34 106.03(13) . . ? C22 C21 C6 104.53(13) . . ? C34 C21 C6 107.23(13) . . ? C23 C22 C27 120.47(16) . . ? C23 C22 C21 126.51(16) . . ? C27 C22 C21 113.02(14) . . ? C22 C23 C24 118.91(18) . . ? C25 C24 C23 120.60(18) . . ? C24 C25 C26 120.63(18) . . ? C27 C26 C25 118.96(19) . . ? C26 C27 C22 120.42(17) . . ? C26 C27 C28 126.71(16) . . ? C22 C27 C28 112.87(14) . . ? C29 C28 C27 106.07(13) . . ? C29 C28 C5 105.71(13) . . ? C27 C28 C5 105.08(13) . . ? C30 C29 C34 120.55(17) . . ? C30 C29 C28 126.59(17) . . ? C34 C29 C28 112.84(14) . . ? C29 C30 C31 118.9(2) . . ? C32 C31 C30 120.73(19) . . ? C31 C32 C33 120.69(19) . . ? C34 C33 C32 118.6(2) . . ? C33 C34 C29 120.59(17) . . ? C33 C34 C21 126.14(17) . . ? C29 C34 C21 113.23(14) . . ? N2 C35 C4 177.12(17) . . ? O1 C38 C37 122.0(3) . . ? O1 C38 C39 120.3(2) . . ? C37 C38 C39 117.6(2) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 67.99 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.351 _refine_diff_density_min -0.322 _refine_diff_density_rms 0.044 _database_code_depnum_ccdc_archive 'CCDC 945643' ####################################################################### # # 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_ic16137 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C23 H18 N2' _chemical_formula_weight 322.39 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pna2(1) 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' _cell_length_a 15.5952(5) _cell_length_b 13.4176(5) _cell_length_c 8.2215(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1720.35(9) _cell_formula_units_Z 4 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used 2200 _cell_measurement_theta_min 5.6720 _cell_measurement_theta_max 74.5180 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.245 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 680 _exptl_absorpt_coefficient_mu 0.564 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.98986 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 200(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Oxford Diffraction Gemini A' _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5422 _diffrn_reflns_av_R_equivalents 0.0333 _diffrn_reflns_av_sigmaI/netI 0.0357 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -4 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 4.35 _diffrn_reflns_theta_max 67.91 _reflns_number_total 2199 _reflns_number_gt 1986 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXTL _computing_publication_material 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^)+(0.0611P)^2^+0.2009P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 1.1(9) _refine_ls_number_reflns 2199 _refine_ls_number_parameters 226 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0467 _refine_ls_R_factor_gt 0.0407 _refine_ls_wR_factor_ref 0.1053 _refine_ls_wR_factor_gt 0.0995 _refine_ls_goodness_of_fit_ref 1.034 _refine_ls_restrained_S_all 1.034 _refine_ls_shift/su_max 0.009 _refine_ls_shift/su_mean 0.001 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 0.13829(13) 0.24740(16) 0.4795(3) 0.0347(5) Uani 1 1 d . . . N2 N 0.50947(17) 0.4969(2) 0.6334(4) 0.0577(7) Uani 1 1 d . . . C1 C 0.21705(15) 0.29579(17) 0.5077(3) 0.0309(5) Uani 1 1 d . . . C2 C 0.27195(18) 0.3260(2) 0.3819(3) 0.0365(6) Uani 1 1 d . . . H2A H 0.2568 0.3119 0.2723 0.044 Uiso 1 1 calc R . . C3 C 0.34757(18) 0.3757(2) 0.4139(3) 0.0370(6) Uani 1 1 d . . . H3A H 0.3841 0.3946 0.3267 0.044 Uiso 1 1 calc R . . C4 C 0.37074(15) 0.39845(17) 0.5739(3) 0.0305(5) Uani 1 1 d . . . C5 C 0.31800(15) 0.36718(17) 0.7013(3) 0.0279(5) Uani 1 1 d . . . C6 C 0.24316(15) 0.31460(17) 0.6671(3) 0.0283(5) Uani 1 1 d . . . C7 C 0.19661(16) 0.28125(18) 0.8223(3) 0.0300(5) Uani 1 1 d . . . H7A H 0.1437 0.2416 0.7995 0.036 Uiso 1 1 calc R . . C8 C 0.17850(16) 0.37709(17) 0.9163(3) 0.0298(5) Uani 1 1 d . . . C9 C 0.10022(16) 0.4103(2) 0.9701(3) 0.0354(6) Uani 1 1 d . . . H9A H 0.0497 0.3731 0.9474 0.042 Uiso 1 1 calc R . . C10 C 0.09538(18) 0.4983(2) 1.0575(4) 0.0412(6) Uani 1 1 d . . . H10A H 0.0412 0.5216 1.0944 0.049 Uiso 1 1 calc R . . C11 C 0.16844(18) 0.5525(2) 1.0916(3) 0.0420(6) Uani 1 1 d . . . H11A H 0.1643 0.6126 1.1521 0.050 Uiso 1 1 calc R . . C12 C 0.24832(17) 0.51929(19) 1.0376(3) 0.0350(6) Uani 1 1 d . . . H12A H 0.2987 0.5564 1.0608 0.042 Uiso 1 1 calc R . . C13 C 0.25300(16) 0.43185(18) 0.9501(3) 0.0292(5) Uani 1 1 d . . . C14 C 0.33403(15) 0.38350(19) 0.8827(3) 0.0303(5) Uani 1 1 d . . . H14A H 0.3870 0.4231 0.9052 0.036 Uiso 1 1 calc R . . C15 C 0.33654(16) 0.27915(18) 0.9567(3) 0.0319(5) Uani 1 1 d . . . C16 C 0.40058(17) 0.2398(2) 1.0524(3) 0.0400(6) Uani 1 1 d . . . H16A H 0.4509 0.2773 1.0752 0.048 Uiso 1 1 calc R . . C17 C 0.3903(2) 0.1440(3) 1.1152(4) 0.0512(8) Uani 1 1 d . . . H17A H 0.4336 0.1162 1.1825 0.061 Uiso 1 1 calc R . . C18 C 0.3179(2) 0.0894(2) 1.0804(4) 0.0513(8) Uani 1 1 d . . . H18A H 0.3119 0.0241 1.1236 0.062 Uiso 1 1 calc R . . C19 C 0.25336(18) 0.12848(19) 0.9829(4) 0.0408(6) Uani 1 1 d . . . H19A H 0.2039 0.0901 0.9576 0.049 Uiso 1 1 calc R . . C20 C 0.26236(16) 0.22425(18) 0.9233(3) 0.0316(5) Uani 1 1 d . . . C21 C 0.1269(2) 0.2014(2) 0.3204(4) 0.0459(7) Uani 1 1 d . . . H21A H 0.1776 0.1615 0.2939 0.069 Uiso 1 1 calc R . . H21B H 0.1193 0.2535 0.2381 0.069 Uiso 1 1 calc R . . H21C H 0.0761 0.1584 0.3224 0.069 Uiso 1 1 calc R . . C22 C 0.06284(19) 0.3070(3) 0.5225(4) 0.0529(8) Uani 1 1 d . . . H22A H 0.0714 0.3372 0.6298 0.079 Uiso 1 1 calc R . . H22B H 0.0120 0.2641 0.5250 0.079 Uiso 1 1 calc R . . H22C H 0.0547 0.3597 0.4413 0.079 Uiso 1 1 calc R . . C23 C 0.44828(17) 0.4529(2) 0.6070(3) 0.0392(6) 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 N1 0.0370(10) 0.0353(10) 0.0317(11) -0.0063(9) -0.0030(9) 0.0010(9) N2 0.0477(14) 0.0717(18) 0.0537(16) -0.0096(14) 0.0113(12) -0.0263(14) C1 0.0367(13) 0.0263(11) 0.0297(13) -0.0024(10) -0.0003(11) 0.0042(9) C2 0.0472(14) 0.0395(14) 0.0229(12) -0.0019(11) 0.0038(11) 0.0014(12) C3 0.0427(14) 0.0382(15) 0.0301(14) 0.0036(11) 0.0130(11) -0.0001(11) C4 0.0317(12) 0.0268(11) 0.0330(14) 0.0012(11) 0.0057(10) -0.0005(9) C5 0.0303(11) 0.0251(11) 0.0283(13) 0.0008(9) 0.0005(10) 0.0041(9) C6 0.0308(11) 0.0263(11) 0.0280(12) -0.0004(10) 0.0043(10) 0.0018(9) C7 0.0332(12) 0.0303(12) 0.0264(12) -0.0006(10) 0.0051(10) -0.0052(10) C8 0.0380(13) 0.0285(12) 0.0230(12) 0.0029(9) 0.0004(10) -0.0004(9) C9 0.0336(12) 0.0380(13) 0.0346(14) 0.0030(11) 0.0026(11) -0.0023(10) C10 0.0413(13) 0.0395(14) 0.0427(15) -0.0002(12) 0.0072(12) 0.0099(11) C11 0.0545(16) 0.0341(13) 0.0375(15) -0.0069(12) 0.0012(13) 0.0064(12) C12 0.0445(14) 0.0295(11) 0.0310(13) 0.0008(10) -0.0012(11) -0.0057(10) C13 0.0365(12) 0.0274(12) 0.0238(12) 0.0040(9) 0.0019(9) -0.0016(9) C14 0.0290(12) 0.0323(13) 0.0297(13) -0.0005(10) -0.0003(10) -0.0033(9) C15 0.0389(13) 0.0344(13) 0.0224(12) -0.0005(10) 0.0073(10) 0.0041(10) C16 0.0372(13) 0.0512(15) 0.0315(14) 0.0006(12) 0.0050(11) 0.0107(12) C17 0.0538(17) 0.0580(18) 0.0417(17) 0.0162(14) 0.0104(14) 0.0245(15) C18 0.068(2) 0.0364(14) 0.0501(18) 0.0162(14) 0.0200(16) 0.0171(14) C19 0.0516(16) 0.0324(13) 0.0385(14) -0.0001(12) 0.0167(13) 0.0006(11) C20 0.0385(12) 0.0303(12) 0.0259(13) -0.0007(10) 0.0113(10) 0.0020(10) C21 0.0514(17) 0.0502(17) 0.0360(15) -0.0088(13) -0.0063(13) -0.0061(13) C22 0.0377(15) 0.0627(18) 0.058(2) -0.0161(17) -0.0034(14) 0.0014(14) C23 0.0410(14) 0.0419(14) 0.0349(14) -0.0017(11) 0.0132(12) -0.0035(12) _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 C1 1.408(3) . ? N1 C21 1.457(4) . ? N1 C22 1.466(4) . ? N2 C23 1.143(4) . ? C1 C6 1.395(4) . ? C1 C2 1.402(4) . ? C2 C3 1.380(4) . ? C3 C4 1.398(4) . ? C4 C5 1.397(3) . ? C4 C23 1.439(4) . ? C5 C6 1.393(3) . ? C5 C14 1.528(3) . ? C6 C7 1.535(3) . ? C7 C20 1.525(4) . ? C7 C8 1.527(3) . ? C8 C9 1.372(4) . ? C8 C13 1.402(4) . ? C9 C10 1.384(4) . ? C10 C11 1.381(4) . ? C11 C12 1.396(4) . ? C12 C13 1.378(4) . ? C13 C14 1.525(3) . ? C14 C15 1.527(3) . ? C15 C16 1.376(4) . ? C15 C20 1.399(4) . ? C16 C17 1.395(4) . ? C17 C18 1.376(5) . ? C18 C19 1.389(5) . ? C19 C20 1.382(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 N1 C21 116.7(2) . . ? C1 N1 C22 114.1(2) . . ? C21 N1 C22 110.4(2) . . ? C6 C1 C2 117.5(2) . . ? C6 C1 N1 119.5(2) . . ? C2 C1 N1 123.0(2) . . ? C3 C2 C1 121.4(2) . . ? C2 C3 C4 120.4(2) . . ? C3 C4 C5 119.2(2) . . ? C3 C4 C23 120.4(2) . . ? C5 C4 C23 120.4(2) . . ? C6 C5 C4 119.6(2) . . ? C6 C5 C14 114.0(2) . . ? C4 C5 C14 126.4(2) . . ? C5 C6 C1 121.7(2) . . ? C5 C6 C7 112.1(2) . . ? C1 C6 C7 126.2(2) . . ? C20 C7 C8 105.7(2) . . ? C20 C7 C6 106.31(19) . . ? C8 C7 C6 105.25(18) . . ? C9 C8 C13 120.2(2) . . ? C9 C8 C7 126.9(2) . . ? C13 C8 C7 112.8(2) . . ? C8 C9 C10 119.5(3) . . ? C11 C10 C9 120.7(3) . . ? C10 C11 C12 120.2(2) . . ? C13 C12 C11 119.0(2) . . ? C12 C13 C8 120.3(2) . . ? C12 C13 C14 126.6(2) . . ? C8 C13 C14 113.1(2) . . ? C13 C14 C5 106.3(2) . . ? C13 C14 C15 105.5(2) . . ? C5 C14 C15 105.2(2) . . ? C16 C15 C20 120.7(2) . . ? C16 C15 C14 126.7(2) . . ? C20 C15 C14 112.5(2) . . ? C15 C16 C17 118.8(3) . . ? C18 C17 C16 120.5(3) . . ? C17 C18 C19 120.9(3) . . ? C20 C19 C18 118.8(3) . . ? C19 C20 C15 120.3(3) . . ? C19 C20 C7 126.2(2) . . ? C15 C20 C7 113.5(2) . . ? N2 C23 C4 179.4(3) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 67.91 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.152 _refine_diff_density_min -0.296 _refine_diff_density_rms 0.046 _database_code_depnum_ccdc_archive 'CCDC 945644' ####################################################################### # # 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_ic16171 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C37 H26 N2' _chemical_formula_weight 498.60 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/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 10.6616(2) _cell_length_b 20.7812(3) _cell_length_c 13.2070(3) _cell_angle_alpha 90.00 _cell_angle_beta 110.460(2) _cell_angle_gamma 90.00 _cell_volume 2741.56(9) _cell_formula_units_Z 4 _cell_measurement_temperature 250(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.208 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1048 _exptl_absorpt_coefficient_mu 0.538 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 250(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Oxford Diffraction Gemini A' _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 19674 _diffrn_reflns_av_R_equivalents 0.0330 _diffrn_reflns_av_sigmaI/netI 0.0236 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 4.16 _diffrn_reflns_theta_max 68.00 _reflns_number_total 4990 _reflns_number_gt 4069 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.32.15 (release 10-01-2008 CrysAlis171 .NET) (compiled Jan 10 2008,16:37:18) ; _computing_cell_refinement ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.32.15 (release 10-01-2008 CrysAlis171 .NET) (compiled Jan 10 2008,16:37:18) ; _computing_data_reduction ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.32.15 (release 10-01-2008 CrysAlis171 .NET) (compiled Jan 10 2008,16:37:18) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXTL _computing_publication_material 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^)+(0.0776P)^2^+0.5679P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4990 _refine_ls_number_parameters 352 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0572 _refine_ls_R_factor_gt 0.0461 _refine_ls_wR_factor_ref 0.1369 _refine_ls_wR_factor_gt 0.1252 _refine_ls_goodness_of_fit_ref 1.031 _refine_ls_restrained_S_all 1.031 _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 0.79170(16) 0.27333(7) 0.89726(12) 0.0507(4) Uani 1 1 d . . . N2 N 0.37412(18) 0.06687(8) 0.53215(15) 0.0664(5) Uani 1 1 d . . . C1 C 0.70683(16) 0.23342(7) 0.81338(13) 0.0369(3) Uani 1 1 d . . . C2 C 0.58342(16) 0.25370(7) 0.74015(13) 0.0368(3) Uani 1 1 d . . . C3 C 0.50127(15) 0.21212(7) 0.66213(12) 0.0358(3) Uani 1 1 d . . . C4 C 0.53931(15) 0.14810(7) 0.65781(12) 0.0341(3) Uani 1 1 d . . . C5 C 0.66462(15) 0.12774(7) 0.72762(12) 0.0345(3) Uani 1 1 d . . . C6 C 0.74791(15) 0.17053(7) 0.80264(12) 0.0350(3) Uani 1 1 d . . . C7 C 0.52476(16) 0.32169(7) 0.73087(13) 0.0383(4) Uani 1 1 d . . . H7A H 0.5814 0.3514 0.7868 0.046 Uiso 1 1 calc R . . C8 C 0.38395(17) 0.31515(8) 0.73328(14) 0.0417(4) Uani 1 1 d . . . C9 C 0.3332(2) 0.34782(9) 0.80224(16) 0.0524(5) Uani 1 1 d . . . H9A H 0.3878 0.3757 0.8555 0.063 Uiso 1 1 calc R . . C10 C 0.1996(2) 0.33838(11) 0.7908(2) 0.0655(6) Uani 1 1 d . . . H10A H 0.1637 0.3601 0.8369 0.079 Uiso 1 1 calc R . . C11 C 0.1195(2) 0.29761(11) 0.7128(2) 0.0649(6) Uani 1 1 d . . . H11A H 0.0295 0.2918 0.7062 0.078 Uiso 1 1 calc R . . C12 C 0.17036(19) 0.26475(9) 0.64339(18) 0.0535(5) Uani 1 1 d . . . H12A H 0.1155 0.2369 0.5902 0.064 Uiso 1 1 calc R . . C13 C 0.30285(17) 0.27388(8) 0.65421(14) 0.0412(4) Uani 1 1 d . . . C14 C 0.37529(15) 0.24427(7) 0.58463(13) 0.0371(3) Uani 1 1 d . . . H14A H 0.3183 0.2145 0.5289 0.044 Uiso 1 1 calc R . . C15 C 0.42697(15) 0.30118(7) 0.53701(13) 0.0354(3) Uani 1 1 d . . . C16 C 0.40206(16) 0.31301(8) 0.42928(13) 0.0407(4) Uani 1 1 d . . . H16A H 0.3486 0.2847 0.3761 0.049 Uiso 1 1 calc R . . C17 C 0.45734(19) 0.36757(9) 0.40044(15) 0.0484(4) Uani 1 1 d . . . H17A H 0.4407 0.3763 0.3271 0.058 Uiso 1 1 calc R . . C18 C 0.53622(19) 0.40895(9) 0.47831(16) 0.0501(4) Uani 1 1 d . . . H18A H 0.5729 0.4456 0.4575 0.060 Uiso 1 1 calc R . . C19 C 0.56206(17) 0.39696(8) 0.58727(15) 0.0428(4) Uani 1 1 d . . . H19A H 0.6159 0.4252 0.6404 0.051 Uiso 1 1 calc R . . C20 C 0.50747(15) 0.34297(7) 0.61612(13) 0.0363(3) Uani 1 1 d . . . C21 C 0.88269(15) 0.14110(7) 0.86764(13) 0.0361(3) Uani 1 1 d . . . H21A H 0.9428 0.1715 0.9201 0.043 Uiso 1 1 calc R . . C22 C 0.94020(16) 0.11709(7) 0.78367(13) 0.0374(3) Uani 1 1 d . . . C23 C 1.06241(17) 0.13327(8) 0.77649(15) 0.0456(4) Uani 1 1 d . . . H23A H 1.1185 0.1631 0.8250 0.055 Uiso 1 1 calc R . . C24 C 1.10177(19) 0.10512(10) 0.69704(17) 0.0554(5) Uani 1 1 d . . . H24A H 1.1853 0.1156 0.6924 0.066 Uiso 1 1 calc R . . C25 C 1.0192(2) 0.06190(10) 0.62494(17) 0.0566(5) Uani 1 1 d . . . H25A H 1.0471 0.0431 0.5716 0.068 Uiso 1 1 calc R . . C26 C 0.89506(19) 0.04576(9) 0.63035(15) 0.0478(4) Uani 1 1 d . . . H26A H 0.8386 0.0166 0.5808 0.057 Uiso 1 1 calc R . . C27 C 0.85643(16) 0.07333(7) 0.70976(13) 0.0376(3) Uani 1 1 d . . . C28 C 0.72605(15) 0.06119(7) 0.72991(13) 0.0358(3) Uani 1 1 d . . . H28A H 0.6656 0.0309 0.6775 0.043 Uiso 1 1 calc R . . C29 C 0.76766(15) 0.03788(7) 0.84678(13) 0.0354(3) Uani 1 1 d . . . C30 C 0.73178(16) -0.01959(7) 0.88183(14) 0.0398(4) Uani 1 1 d . . . H30A H 0.6759 -0.0488 0.8320 0.048 Uiso 1 1 calc R . . C31 C 0.77943(17) -0.03364(8) 0.99174(15) 0.0457(4) Uani 1 1 d . . . H31A H 0.7555 -0.0726 1.0163 0.055 Uiso 1 1 calc R . . C32 C 0.86162(17) 0.00925(8) 1.06506(15) 0.0453(4) Uani 1 1 d . . . H32A H 0.8928 -0.0006 1.1392 0.054 Uiso 1 1 calc R . . C33 C 0.89858(16) 0.06693(8) 1.02995(14) 0.0407(4) Uani 1 1 d . . . H33A H 0.9547 0.0961 1.0799 0.049 Uiso 1 1 calc R . . C34 C 0.85193(15) 0.08093(7) 0.92085(13) 0.0354(3) Uani 1 1 d . . . C35 C 0.44832(17) 0.10301(7) 0.58605(14) 0.0413(4) Uani 1 1 d . . . C36 C 0.8598(3) 0.32437(14) 0.8689(2) 0.0897(9) Uani 1 1 d . . . H36A H 0.9136 0.3471 0.9337 0.134 Uiso 1 1 calc R . . H36B H 0.7953 0.3538 0.8211 0.134 Uiso 1 1 calc R . . H36C H 0.9174 0.3074 0.8324 0.134 Uiso 1 1 calc R . . C37 C 0.7609(4) 0.27852(18) 0.9914(2) 0.1137(13) Uani 1 1 d . . . H37A H 0.8251 0.3067 1.0422 0.171 Uiso 1 1 calc R . . H37B H 0.7646 0.2363 1.0236 0.171 Uiso 1 1 calc R . . H37C H 0.6716 0.2962 0.9739 0.171 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 0.0598(9) 0.0380(7) 0.0462(8) -0.0104(6) 0.0083(7) -0.0080(7) N2 0.0634(11) 0.0503(9) 0.0660(11) -0.0044(8) -0.0019(9) -0.0156(8) C1 0.0407(8) 0.0319(7) 0.0358(8) -0.0009(6) 0.0103(6) -0.0010(6) C2 0.0426(8) 0.0307(7) 0.0377(8) 0.0009(6) 0.0147(7) 0.0018(6) C3 0.0357(8) 0.0337(8) 0.0367(8) 0.0029(6) 0.0110(6) 0.0007(6) C4 0.0351(8) 0.0320(7) 0.0335(7) 0.0002(6) 0.0098(6) -0.0017(6) C5 0.0369(8) 0.0299(7) 0.0365(8) -0.0007(6) 0.0127(6) -0.0008(6) C6 0.0354(8) 0.0330(7) 0.0341(8) 0.0012(6) 0.0089(6) -0.0013(6) C7 0.0439(9) 0.0321(8) 0.0370(8) -0.0009(6) 0.0119(7) 0.0024(6) C8 0.0512(9) 0.0355(8) 0.0419(9) 0.0117(7) 0.0205(8) 0.0099(7) C9 0.0717(12) 0.0440(9) 0.0505(10) 0.0133(8) 0.0328(9) 0.0174(9) C10 0.0796(15) 0.0608(12) 0.0759(14) 0.0233(11) 0.0521(13) 0.0273(11) C11 0.0558(12) 0.0665(13) 0.0863(16) 0.0285(12) 0.0423(12) 0.0178(10) C12 0.0447(10) 0.0487(10) 0.0690(12) 0.0189(9) 0.0223(9) 0.0056(8) C13 0.0427(8) 0.0358(8) 0.0474(9) 0.0134(7) 0.0185(7) 0.0078(7) C14 0.0357(8) 0.0327(7) 0.0396(8) 0.0020(6) 0.0093(6) 0.0010(6) C15 0.0330(7) 0.0329(7) 0.0405(8) 0.0014(6) 0.0129(6) 0.0055(6) C16 0.0401(8) 0.0423(8) 0.0402(9) -0.0021(7) 0.0147(7) 0.0079(7) C17 0.0534(10) 0.0567(10) 0.0430(9) 0.0075(8) 0.0269(8) 0.0068(8) C18 0.0519(10) 0.0482(10) 0.0596(11) 0.0082(8) 0.0314(9) -0.0026(8) C19 0.0404(8) 0.0375(8) 0.0521(10) -0.0021(7) 0.0182(7) -0.0028(7) C20 0.0362(8) 0.0336(7) 0.0400(8) 0.0006(6) 0.0145(6) 0.0052(6) C21 0.0342(8) 0.0305(7) 0.0385(8) -0.0006(6) 0.0062(6) -0.0025(6) C22 0.0370(8) 0.0306(7) 0.0421(8) 0.0074(6) 0.0106(7) 0.0025(6) C23 0.0393(9) 0.0411(9) 0.0534(10) 0.0098(7) 0.0125(8) -0.0025(7) C24 0.0475(10) 0.0594(11) 0.0671(12) 0.0127(9) 0.0297(9) 0.0010(8) C25 0.0606(12) 0.0599(11) 0.0589(11) 0.0042(9) 0.0328(10) 0.0063(9) C26 0.0520(10) 0.0458(9) 0.0467(10) -0.0012(7) 0.0189(8) 0.0034(8) C27 0.0383(8) 0.0324(7) 0.0409(8) 0.0046(6) 0.0122(7) 0.0033(6) C28 0.0348(8) 0.0305(7) 0.0389(8) -0.0029(6) 0.0089(6) -0.0007(6) C29 0.0329(7) 0.0309(7) 0.0423(8) -0.0006(6) 0.0133(6) 0.0034(6) C30 0.0375(8) 0.0311(7) 0.0526(10) 0.0000(7) 0.0178(7) 0.0012(6) C31 0.0451(9) 0.0371(8) 0.0582(11) 0.0121(7) 0.0223(8) 0.0050(7) C32 0.0451(9) 0.0469(9) 0.0442(9) 0.0118(7) 0.0159(8) 0.0127(7) C33 0.0364(8) 0.0407(8) 0.0414(9) 0.0007(7) 0.0091(7) 0.0051(6) C34 0.0323(7) 0.0315(7) 0.0416(8) 0.0011(6) 0.0120(6) 0.0044(6) C35 0.0411(8) 0.0343(8) 0.0431(9) 0.0025(7) 0.0078(7) -0.0002(7) C36 0.0892(18) 0.102(2) 0.0784(17) -0.0273(15) 0.0296(14) -0.0539(16) C37 0.130(3) 0.163(3) 0.0533(14) -0.0479(18) 0.0387(16) -0.077(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 N1 C37 1.397(3) . ? N1 C36 1.408(3) . ? N1 C1 1.426(2) . ? N2 C35 1.141(2) . ? C1 C2 1.398(2) . ? C1 C6 1.401(2) . ? C2 C3 1.395(2) . ? C2 C7 1.533(2) . ? C3 C4 1.398(2) . ? C3 C14 1.529(2) . ? C4 C5 1.397(2) . ? C4 C35 1.440(2) . ? C5 C6 1.395(2) . ? C5 C28 1.526(2) . ? C6 C21 1.521(2) . ? C7 C8 1.519(2) . ? C7 C20 1.527(2) . ? C8 C9 1.389(2) . ? C8 C13 1.394(2) . ? C9 C10 1.393(3) . ? C10 C11 1.376(3) . ? C11 C12 1.396(3) . ? C12 C13 1.382(2) . ? C13 C14 1.522(2) . ? C14 C15 1.530(2) . ? C15 C16 1.375(2) . ? C15 C20 1.398(2) . ? C16 C17 1.391(3) . ? C17 C18 1.378(3) . ? C18 C19 1.390(3) . ? C19 C20 1.377(2) . ? C21 C34 1.525(2) . ? C21 C22 1.526(2) . ? C22 C23 1.381(2) . ? C22 C27 1.403(2) . ? C23 C24 1.388(3) . ? C24 C25 1.379(3) . ? C25 C26 1.391(3) . ? C26 C27 1.378(2) . ? C27 C28 1.525(2) . ? C28 C29 1.528(2) . ? C29 C30 1.382(2) . ? C29 C34 1.397(2) . ? C30 C31 1.391(3) . ? C31 C32 1.381(3) . ? C32 C33 1.391(2) . ? C33 C34 1.381(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 C37 N1 C36 118.8(2) . . ? C37 N1 C1 116.98(18) . . ? C36 N1 C1 118.54(17) . . ? C2 C1 C6 117.58(14) . . ? C2 C1 N1 123.39(14) . . ? C6 C1 N1 119.03(14) . . ? C3 C2 C1 121.36(14) . . ? C3 C2 C7 112.27(13) . . ? C1 C2 C7 126.32(14) . . ? C2 C3 C4 120.24(14) . . ? C2 C3 C14 113.69(13) . . ? C4 C3 C14 126.03(14) . . ? C5 C4 C3 119.04(14) . . ? C5 C4 C35 120.38(13) . . ? C3 C4 C35 120.52(14) . . ? C6 C5 C4 120.00(14) . . ? C6 C5 C28 113.66(13) . . ? C4 C5 C28 126.32(13) . . ? C5 C6 C1 121.51(14) . . ? C5 C6 C21 112.70(13) . . ? C1 C6 C21 125.80(14) . . ? C8 C7 C20 105.63(13) . . ? C8 C7 C2 107.13(13) . . ? C20 C7 C2 104.52(12) . . ? C9 C8 C13 120.68(17) . . ? C9 C8 C7 125.80(17) . . ? C13 C8 C7 113.47(14) . . ? C8 C9 C10 118.6(2) . . ? C11 C10 C9 120.75(19) . . ? C10 C11 C12 120.75(19) . . ? C13 C12 C11 118.8(2) . . ? C12 C13 C8 120.39(17) . . ? C12 C13 C14 126.73(17) . . ? C8 C13 C14 112.85(14) . . ? C13 C14 C3 106.56(13) . . ? C13 C14 C15 105.51(12) . . ? C3 C14 C15 104.76(12) . . ? C16 C15 C20 120.53(15) . . ? C16 C15 C14 126.62(15) . . ? C20 C15 C14 112.84(14) . . ? C15 C16 C17 118.81(16) . . ? C18 C17 C16 120.71(16) . . ? C17 C18 C19 120.60(16) . . ? C20 C19 C18 118.84(16) . . ? C19 C20 C15 120.50(15) . . ? C19 C20 C7 126.46(15) . . ? C15 C20 C7 113.04(13) . . ? C6 C21 C34 106.07(12) . . ? C6 C21 C22 105.16(12) . . ? C34 C21 C22 105.81(12) . . ? C23 C22 C27 119.78(16) . . ? C23 C22 C21 126.77(15) . . ? C27 C22 C21 113.44(14) . . ? C22 C23 C24 119.42(17) . . ? C25 C24 C23 120.51(17) . . ? C24 C25 C26 120.70(18) . . ? C27 C26 C25 118.79(18) . . ? C26 C27 C22 120.80(16) . . ? C26 C27 C28 126.66(15) . . ? C22 C27 C28 112.53(14) . . ? C27 C28 C5 104.93(12) . . ? C27 C28 C29 105.56(12) . . ? C5 C28 C29 106.17(12) . . ? C30 C29 C34 120.30(15) . . ? C30 C29 C28 126.56(14) . . ? C34 C29 C28 113.14(13) . . ? C29 C30 C31 119.21(16) . . ? C32 C31 C30 120.46(15) . . ? C31 C32 C33 120.45(16) . . ? C34 C33 C32 119.25(16) . . ? C33 C34 C29 120.32(14) . . ? C33 C34 C21 126.62(14) . . ? C29 C34 C21 113.06(14) . . ? N2 C35 C4 177.4(2) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 68.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.254 _refine_diff_density_min -0.223 _refine_diff_density_rms 0.039 _database_code_depnum_ccdc_archive 'CCDC 945645' ####################################################################### # # 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_ic14848 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C27 H18 N2' _chemical_formula_weight 370.43 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pbca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 16.0572(4) _cell_length_b 13.6979(3) _cell_length_c 17.9652(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3951.44(16) _cell_formula_units_Z 8 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 3642 _cell_measurement_theta_min 3.2236 _cell_measurement_theta_max 77.0052 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.245 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1552 _exptl_absorpt_coefficient_mu 0.564 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.79578 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Oxford Diffraction Gemini A' _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7711 _diffrn_reflns_av_R_equivalents 0.0253 _diffrn_reflns_av_sigmaI/netI 0.0273 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 4.91 _diffrn_reflns_theta_max 67.96 _reflns_number_total 3572 _reflns_number_gt 2691 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXTL _computing_publication_material 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^)+(0.0781P)^2^+0.7365P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3572 _refine_ls_number_parameters 266 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0658 _refine_ls_R_factor_gt 0.0497 _refine_ls_wR_factor_ref 0.1466 _refine_ls_wR_factor_gt 0.1310 _refine_ls_goodness_of_fit_ref 1.009 _refine_ls_restrained_S_all 1.009 _refine_ls_shift/su_max 0.025 _refine_ls_shift/su_mean 0.002 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 0.10748(13) 0.15272(13) 0.41800(9) 0.0556(5) Uani 1 1 d . . . N2 N 0.07224(15) 0.19008(16) 0.04422(10) 0.0784(6) Uani 1 1 d . . . C1 C 0.14088(12) 0.07011(13) 0.45515(9) 0.0444(4) Uani 1 1 d . . . C2 C 0.09725(15) -0.01601(16) 0.45799(14) 0.0666(6) Uani 1 1 d . . . H2A H 0.0454 -0.0203 0.4352 0.080 Uiso 1 1 calc R . . C3 C 0.12951(18) -0.09627(17) 0.49432(14) 0.0756(7) Uani 1 1 d . . . H3A H 0.0995 -0.1543 0.4954 0.091 Uiso 1 1 calc R . . C4 C 0.20467(17) -0.09116(16) 0.52847(12) 0.0687(6) Uani 1 1 d . . . H4A H 0.2259 -0.1450 0.5536 0.082 Uiso 1 1 calc R . . C5 C 0.24879(16) -0.00600(18) 0.52549(14) 0.0790(8) Uani 1 1 d . . . H5A H 0.3010 -0.0024 0.5478 0.095 Uiso 1 1 calc R . . C6 C 0.21660(15) 0.07505(16) 0.48960(12) 0.0660(6) Uani 1 1 d . . . H6A H 0.2466 0.1331 0.4889 0.079 Uiso 1 1 calc R . . C7 C 0.09906(11) 0.15844(12) 0.34183(9) 0.0381(4) Uani 1 1 d . . . C8 C 0.13329(11) 0.08685(13) 0.29516(10) 0.0430(4) Uani 1 1 d . . . H8A H 0.1619 0.0346 0.3161 0.052 Uiso 1 1 calc R . . C9 C 0.12546(11) 0.09232(13) 0.21940(10) 0.0429(4) Uani 1 1 d . . . H9A H 0.1482 0.0435 0.1897 0.051 Uiso 1 1 calc R . . C10 C 0.08361(11) 0.17070(12) 0.18630(9) 0.0387(4) Uani 1 1 d . . . C11 C 0.04976(9) 0.24251(12) 0.23214(9) 0.0349(4) Uani 1 1 d . . . C12 C 0.05656(9) 0.23654(12) 0.30899(9) 0.0347(4) Uani 1 1 d . . . C13 C 0.01537(11) 0.32247(11) 0.34909(9) 0.0384(4) Uani 1 1 d . . . H13A H 0.0198 0.3182 0.4034 0.046 Uiso 1 1 calc R . . C14 C 0.05634(10) 0.41363(12) 0.31718(10) 0.0406(4) Uani 1 1 d . . . C15 C 0.09794(13) 0.48497(14) 0.35650(12) 0.0534(5) Uani 1 1 d . . . H15A H 0.1018 0.4813 0.4081 0.064 Uiso 1 1 calc R . . C16 C 0.13395(14) 0.56231(15) 0.31834(15) 0.0651(6) Uani 1 1 d . . . H16A H 0.1618 0.6109 0.3446 0.078 Uiso 1 1 calc R . . C17 C 0.12876(13) 0.56766(15) 0.24186(14) 0.0625(6) Uani 1 1 d . . . H17A H 0.1533 0.6196 0.2168 0.075 Uiso 1 1 calc R . . C18 C 0.08700(11) 0.49578(14) 0.20214(12) 0.0504(5) Uani 1 1 d . . . H18A H 0.0836 0.4993 0.1505 0.060 Uiso 1 1 calc R . . C19 C 0.05058(10) 0.41906(12) 0.23979(10) 0.0398(4) Uani 1 1 d . . . C20 C 0.00360(11) 0.33318(12) 0.20583(9) 0.0386(4) Uani 1 1 d . . . H20A H -0.0007 0.3372 0.1515 0.046 Uiso 1 1 calc R . . C21 C -0.08106(11) 0.32951(11) 0.24428(11) 0.0393(4) Uani 1 1 d . . . C22 C -0.15824(12) 0.33035(12) 0.21041(12) 0.0484(5) Uani 1 1 d . . . H22A H -0.1627 0.3329 0.1588 0.058 Uiso 1 1 calc R . . C23 C -0.22925(12) 0.32725(14) 0.25490(14) 0.0590(6) Uani 1 1 d . . . H23A H -0.2816 0.3283 0.2328 0.071 Uiso 1 1 calc R . . C24 C -0.22266(12) 0.32262(14) 0.33075(14) 0.0599(6) Uani 1 1 d . . . H24A H -0.2707 0.3207 0.3596 0.072 Uiso 1 1 calc R . . C25 C -0.14518(12) 0.32075(13) 0.36532(12) 0.0507(5) Uani 1 1 d . . . H25A H -0.1411 0.3173 0.4169 0.061 Uiso 1 1 calc R . . C26 C -0.07444(11) 0.32416(11) 0.32161(10) 0.0402(4) Uani 1 1 d . . . C27 C 0.07700(13) 0.17972(14) 0.10715(11) 0.0501(5) Uani 1 1 d . . . H1 H 0.1036(14) 0.2021(17) 0.4407(13) 0.063(7) Uiso 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 N1 0.0854(13) 0.0450(9) 0.0366(8) -0.0044(7) -0.0137(8) 0.0213(9) N2 0.1166(18) 0.0811(14) 0.0374(10) 0.0020(9) -0.0037(10) 0.0083(13) C1 0.0564(11) 0.0449(10) 0.0319(8) 0.0000(7) -0.0052(8) 0.0085(9) C2 0.0653(13) 0.0596(13) 0.0748(15) 0.0065(11) -0.0210(11) -0.0029(11) C3 0.0982(19) 0.0512(12) 0.0775(16) 0.0134(11) -0.0128(14) -0.0091(13) C4 0.0948(18) 0.0563(13) 0.0551(12) 0.0150(10) -0.0094(13) 0.0179(13) C5 0.0756(15) 0.0790(17) 0.0825(17) 0.0178(14) -0.0329(14) 0.0092(13) C6 0.0711(14) 0.0590(13) 0.0678(14) 0.0121(10) -0.0219(12) -0.0063(11) C7 0.0406(9) 0.0363(8) 0.0373(9) 0.0004(7) -0.0053(7) 0.0008(7) C8 0.0474(10) 0.0370(9) 0.0446(9) 0.0023(7) -0.0042(8) 0.0074(8) C9 0.0499(10) 0.0374(9) 0.0414(9) -0.0052(7) 0.0041(8) 0.0060(8) C10 0.0408(9) 0.0405(9) 0.0347(8) -0.0010(7) 0.0002(7) -0.0028(7) C11 0.0310(8) 0.0357(8) 0.0379(9) 0.0025(7) -0.0011(7) -0.0012(7) C12 0.0333(8) 0.0335(8) 0.0373(8) -0.0002(7) -0.0008(7) 0.0004(7) C13 0.0421(9) 0.0372(8) 0.0358(8) 0.0010(7) 0.0009(7) 0.0053(7) C14 0.0358(8) 0.0357(9) 0.0503(10) -0.0003(8) -0.0010(8) 0.0052(7) C15 0.0550(11) 0.0442(10) 0.0610(12) -0.0086(9) -0.0079(9) 0.0026(9) C16 0.0617(13) 0.0430(11) 0.0905(17) -0.0073(11) -0.0101(12) -0.0086(10) C17 0.0514(12) 0.0444(11) 0.0916(17) 0.0139(11) -0.0010(11) -0.0077(10) C18 0.0407(9) 0.0466(11) 0.0640(12) 0.0134(9) -0.0004(9) -0.0003(8) C19 0.0325(8) 0.0359(8) 0.0510(10) 0.0051(8) -0.0013(7) 0.0038(7) C20 0.0375(9) 0.0410(9) 0.0373(8) 0.0063(7) -0.0019(7) 0.0009(7) C21 0.0367(9) 0.0303(8) 0.0509(10) 0.0053(7) -0.0009(8) 0.0011(7) C22 0.0415(10) 0.0390(9) 0.0649(12) 0.0052(8) -0.0091(9) 0.0012(8) C23 0.0344(10) 0.0516(11) 0.0910(16) 0.0025(11) -0.0047(10) 0.0005(9) C24 0.0403(10) 0.0533(11) 0.0861(16) 0.0029(11) 0.0174(11) -0.0003(9) C25 0.0492(10) 0.0427(10) 0.0601(12) 0.0033(8) 0.0127(9) 0.0037(9) C26 0.0409(9) 0.0306(8) 0.0491(10) 0.0033(7) 0.0048(8) 0.0034(7) C27 0.0622(12) 0.0475(11) 0.0406(11) -0.0015(8) 0.0008(9) 0.0030(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 N1 C7 1.377(2) . ? N1 C1 1.419(2) . ? N2 C27 1.142(3) . ? C1 C6 1.366(3) . ? C1 C2 1.373(3) . ? C2 C3 1.379(3) . ? C3 C4 1.356(3) . ? C4 C5 1.366(3) . ? C5 C6 1.384(3) . ? C7 C12 1.399(2) . ? C7 C8 1.402(2) . ? C8 C9 1.369(2) . ? C9 C10 1.399(2) . ? C10 C11 1.393(2) . ? C10 C27 1.431(2) . ? C11 C12 1.387(2) . ? C11 C20 1.522(2) . ? C12 C13 1.530(2) . ? C13 C14 1.523(2) . ? C13 C26 1.524(2) . ? C14 C15 1.379(3) . ? C14 C19 1.395(3) . ? C15 C16 1.388(3) . ? C16 C17 1.378(3) . ? C17 C18 1.389(3) . ? C18 C19 1.380(2) . ? C19 C20 1.525(2) . ? C20 C21 1.526(2) . ? C21 C22 1.380(3) . ? C21 C26 1.395(3) . ? C22 C23 1.393(3) . ? C23 C24 1.368(3) . ? C24 C25 1.391(3) . ? C25 C26 1.382(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C7 N1 C1 123.35(15) . . ? C6 C1 C2 118.68(18) . . ? C6 C1 N1 120.66(18) . . ? C2 C1 N1 120.66(18) . . ? C1 C2 C3 120.7(2) . . ? C4 C3 C2 120.5(2) . . ? C3 C4 C5 119.2(2) . . ? C4 C5 C6 120.6(2) . . ? C1 C6 C5 120.2(2) . . ? N1 C7 C12 120.68(15) . . ? N1 C7 C8 121.05(16) . . ? C12 C7 C8 118.27(15) . . ? C9 C8 C7 121.35(16) . . ? C8 C9 C10 120.57(16) . . ? C11 C10 C9 118.55(15) . . ? C11 C10 C27 119.83(16) . . ? C9 C10 C27 121.60(16) . . ? C12 C11 C10 121.06(15) . . ? C12 C11 C20 113.30(14) . . ? C10 C11 C20 125.64(14) . . ? C11 C12 C7 120.20(15) . . ? C11 C12 C13 112.90(14) . . ? C7 C12 C13 126.88(14) . . ? C14 C13 C26 105.91(13) . . ? C14 C13 C12 105.46(13) . . ? C26 C13 C12 105.55(13) . . ? C15 C14 C19 120.32(17) . . ? C15 C14 C13 126.69(17) . . ? C19 C14 C13 112.96(15) . . ? C14 C15 C16 119.3(2) . . ? C17 C16 C15 120.51(19) . . ? C16 C17 C18 120.25(19) . . ? C19 C18 C17 119.5(2) . . ? C18 C19 C14 120.07(17) . . ? C18 C19 C20 126.95(17) . . ? C14 C19 C20 112.98(14) . . ? C11 C20 C19 105.33(13) . . ? C11 C20 C21 105.46(13) . . ? C19 C20 C21 106.56(14) . . ? C22 C21 C26 120.50(17) . . ? C22 C21 C20 126.87(18) . . ? C26 C21 C20 112.62(15) . . ? C21 C22 C23 118.80(19) . . ? C24 C23 C22 120.63(19) . . ? C23 C24 C25 120.98(19) . . ? C26 C25 C24 118.76(19) . . ? C25 C26 C21 120.33(17) . . ? C25 C26 C13 126.38(17) . . ? C21 C26 C13 113.29(15) . . ? N2 C27 C10 177.8(2) . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 67.96 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.173 _refine_diff_density_min -0.225 _refine_diff_density_rms 0.044 _database_code_depnum_ccdc_archive 'CCDC 945646' ####################################################################### # # 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_ic14643 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C83 H54 Cl2 N4' _chemical_formula_weight 1178.20 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 11.7562(4) _cell_length_b 16.1045(4) _cell_length_c 17.9894(4) _cell_angle_alpha 91.242(2) _cell_angle_beta 100.219(2) _cell_angle_gamma 104.494(3) _cell_volume 3237.37(15) _cell_formula_units_Z 2 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 12941 _cell_measurement_theta_min 2.9272 _cell_measurement_theta_max 30.1471 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.209 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1228 _exptl_absorpt_coefficient_mu 0.150 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.99560 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET) (compiled Aug 27 2010,11:50:40) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Oxford Diffraction Gemini A' _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 37333 _diffrn_reflns_av_R_equivalents 0.0236 _diffrn_reflns_av_sigmaI/netI 0.0330 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.93 _diffrn_reflns_theta_max 27.50 _reflns_number_total 14856 _reflns_number_gt 9900 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET) (compiled Aug 27 2010,11:50:40) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET) (compiled Aug 27 2010,11:50:40) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET) (compiled Aug 27 2010,11:50:40) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXTL _computing_publication_material 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 14856 _refine_ls_number_parameters 838 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1474 _refine_ls_R_factor_gt 0.1122 _refine_ls_wR_factor_ref 0.3657 _refine_ls_wR_factor_gt 0.3451 _refine_ls_goodness_of_fit_ref 2.337 _refine_ls_restrained_S_all 2.337 _refine_ls_shift/su_max 0.114 _refine_ls_shift/su_mean 0.020 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 0.6107(3) 0.67781(18) 0.39705(15) 0.0404(7) Uani 1 1 d . . . H1 H 0.602(4) 0.726(3) 0.435(2) 0.068(12) Uiso 1 1 d . . . N2 N 0.4691(3) 0.7321(2) 0.02211(17) 0.0592(9) Uani 1 1 d . . . C1 C 0.5834(3) 0.69325(19) 0.32018(17) 0.0315(7) Uani 1 1 d . . . C2 C 0.4849(3) 0.72509(19) 0.29235(16) 0.0307(7) Uani 1 1 d . . . C3 C 0.4561(3) 0.73857(18) 0.21602(17) 0.0313(7) Uani 1 1 d . . . C4 C 0.5264(3) 0.72194(19) 0.16604(17) 0.0325(7) Uani 1 1 d . . . C5 C 0.6289(3) 0.69375(19) 0.19396(17) 0.0338(7) Uani 1 1 d . . . C6 C 0.6561(3) 0.67953(19) 0.26999(17) 0.0329(7) Uani 1 1 d . . . C7 C 0.3934(3) 0.74319(19) 0.33737(17) 0.0327(7) Uani 1 1 d . . . H7A H 0.4129 0.7338 0.3913 0.039 Uiso 1 1 calc R . . C8 C 0.2721(3) 0.6852(2) 0.29776(18) 0.0358(7) Uani 1 1 d . . . C9 C 0.1941(3) 0.6247(2) 0.3298(2) 0.0444(8) Uani 1 1 d . . . H9A H 0.2126 0.6152 0.3809 0.053 Uiso 1 1 calc R . . C10 C 0.0874(3) 0.5779(3) 0.2853(3) 0.0584(11) Uani 1 1 d . . . H10A H 0.0341 0.5372 0.3069 0.070 Uiso 1 1 calc R . . C11 C 0.0600(3) 0.5909(3) 0.2105(3) 0.0568(11) Uani 1 1 d . . . H11A H -0.0119 0.5591 0.1814 0.068 Uiso 1 1 calc R . . C12 C 0.1398(3) 0.6521(2) 0.1770(2) 0.0466(9) Uani 1 1 d . . . H12A H 0.1217 0.6610 0.1259 0.056 Uiso 1 1 calc R . . C13 C 0.2444(3) 0.69803(19) 0.22102(18) 0.0340(7) Uani 1 1 d . . . C14 C 0.3417(3) 0.76782(19) 0.19538(17) 0.0341(7) Uani 1 1 d . . . H14A H 0.3225 0.7774 0.1415 0.041 Uiso 1 1 calc R . . C15 C 0.3568(3) 0.84757(19) 0.24673(18) 0.0345(7) Uani 1 1 d . . . C16 C 0.3433(3) 0.9258(2) 0.2237(2) 0.0446(8) Uani 1 1 d . . . H16A H 0.3259 0.9349 0.1725 0.054 Uiso 1 1 calc R . . C17 C 0.3562(4) 0.9921(2) 0.2795(3) 0.0583(11) Uani 1 1 d . . . H17A H 0.3460 1.0452 0.2650 0.070 Uiso 1 1 calc R . . C18 C 0.3838(4) 0.9787(2) 0.3552(2) 0.0555(10) Uani 1 1 d . . . H18A H 0.3932 1.0232 0.3915 0.067 Uiso 1 1 calc R . . C19 C 0.3978(3) 0.8991(2) 0.3777(2) 0.0459(9) Uani 1 1 d . . . H19A H 0.4158 0.8900 0.4289 0.055 Uiso 1 1 calc R . . C20 C 0.3849(3) 0.8337(2) 0.32358(18) 0.0353(7) Uani 1 1 d . . . C21 C 0.7190(3) 0.6791(2) 0.14805(19) 0.0405(8) Uani 1 1 d . . . H21A H 0.6982 0.6890 0.0944 0.049 Uiso 1 1 calc R . . C22 C 0.7284(3) 0.5872(2) 0.1614(2) 0.0415(8) Uani 1 1 d . . . C23 C 0.7106(3) 0.5221(3) 0.1048(2) 0.0552(10) Uani 1 1 d . . . H23A H 0.6916 0.5322 0.0540 0.066 Uiso 1 1 calc R . . C24 C 0.7220(4) 0.4425(3) 0.1261(3) 0.0677(12) Uani 1 1 d . . . H24A H 0.7087 0.3978 0.0894 0.081 Uiso 1 1 calc R . . C25 C 0.7528(4) 0.4287(2) 0.2011(3) 0.0618(11) Uani 1 1 d . . . H25A H 0.7621 0.3749 0.2144 0.074 Uiso 1 1 calc R . . C26 C 0.7705(3) 0.4930(2) 0.2574(2) 0.0479(9) Uani 1 1 d . . . H26A H 0.7908 0.4830 0.3082 0.057 Uiso 1 1 calc R . . C27 C 0.7572(3) 0.5729(2) 0.2362(2) 0.0392(8) Uani 1 1 d . . . C28 C 0.7734(3) 0.6525(2) 0.28954(19) 0.0383(7) Uani 1 1 d . . . H28A H 0.7950 0.6427 0.3432 0.046 Uiso 1 1 calc R . . C29 C 0.8662(3) 0.7237(2) 0.2625(2) 0.0453(9) Uani 1 1 d . . . C30 C 0.9726(3) 0.7723(3) 0.3081(3) 0.0580(11) Uani 1 1 d . . . H30A H 0.9925 0.7622 0.3589 0.070 Uiso 1 1 calc R . . C31 C 1.0466(4) 0.8354(3) 0.2755(4) 0.0791(16) Uani 1 1 d . . . H31A H 1.1173 0.8687 0.3048 0.095 Uiso 1 1 calc R . . C32 C 1.0180(4) 0.8497(3) 0.2013(4) 0.0786(15) Uani 1 1 d . . . H32A H 1.0705 0.8918 0.1804 0.094 Uiso 1 1 calc R . . C33 C 0.9130(4) 0.8033(3) 0.1562(3) 0.0696(13) Uani 1 1 d . . . H33A H 0.8928 0.8154 0.1060 0.083 Uiso 1 1 calc R . . C34 C 0.8372(3) 0.7376(2) 0.1875(2) 0.0454(9) Uani 1 1 d . . . C35 C 0.6200(3) 0.5960(2) 0.42080(18) 0.0363(7) Uani 1 1 d . . . C36 C 0.5886(3) 0.5241(2) 0.37335(19) 0.0428(8) Uani 1 1 d . . . H36A H 0.5587 0.5275 0.3224 0.051 Uiso 1 1 calc R . . C37 C 0.6001(4) 0.4461(2) 0.3992(2) 0.0548(10) Uani 1 1 d . . . H37A H 0.5796 0.3979 0.3654 0.066 Uiso 1 1 calc R . . C38 C 0.6413(4) 0.4390(2) 0.4739(2) 0.0559(10) Uani 1 1 d . . . H38A H 0.6507 0.3866 0.4912 0.067 Uiso 1 1 calc R . . C39 C 0.6686(4) 0.5104(3) 0.5233(2) 0.0583(11) Uani 1 1 d . . . H39A H 0.6928 0.5056 0.5747 0.070 Uiso 1 1 calc R . . C40 C 0.6609(3) 0.5888(2) 0.49778(19) 0.0471(9) Uani 1 1 d . . . H40A H 0.6827 0.6371 0.5316 0.057 Uiso 1 1 calc R . . C41 C 0.4940(3) 0.7289(2) 0.08639(18) 0.0386(8) Uani 1 1 d . . . N3 N 0.6105(3) 0.1962(2) 0.12999(17) 0.0473(7) Uani 1 1 d D . . H3 H 0.584(4) 0.226(2) 0.0902(18) 0.062(12) Uiso 1 1 d D . . N4 N 0.4379(3) 0.2191(2) 0.46848(17) 0.0550(8) Uani 1 1 d . . . C42 C 0.5730(3) 0.2029(2) 0.19881(17) 0.0347(7) Uani 1 1 d . . . C43 C 0.4673(3) 0.22617(19) 0.20338(17) 0.0337(7) Uani 1 1 d . . . C44 C 0.4320(3) 0.23282(19) 0.27222(17) 0.0347(7) Uani 1 1 d . . . C45 C 0.4998(3) 0.21442(19) 0.33865(17) 0.0338(7) Uani 1 1 d . . . C46 C 0.6063(3) 0.1923(2) 0.33477(18) 0.0365(7) Uani 1 1 d . . . C47 C 0.6428(3) 0.1878(2) 0.26610(18) 0.0355(7) Uani 1 1 d . . . C48 C 0.7662(3) 0.1697(2) 0.2742(2) 0.0443(8) Uani 1 1 d . . . H48A H 0.7930 0.1672 0.2258 0.053 Uiso 1 1 calc R . . C49 C 0.8493(3) 0.2407(2) 0.3309(2) 0.0517(10) Uani 1 1 d . . . C50 C 0.9515(4) 0.2977(3) 0.3177(3) 0.0698(13) Uani 1 1 d . . . H50A H 0.9761 0.2959 0.2714 0.084 Uiso 1 1 calc R . . C51 C 1.0168(5) 0.3584(3) 0.3766(4) 0.095(2) Uani 1 1 d . . . H51A H 1.0860 0.3975 0.3691 0.114 Uiso 1 1 calc R . . C52 C 0.9820(5) 0.3618(4) 0.4446(4) 0.0936(19) Uani 1 1 d . . . H52A H 1.0280 0.4026 0.4826 0.112 Uiso 1 1 calc R . . C53 C 0.8763(4) 0.3038(3) 0.4579(3) 0.0747(14) Uani 1 1 d . . . H53A H 0.8511 0.3061 0.5039 0.090 Uiso 1 1 calc R . . C54 C 0.8117(3) 0.2434(2) 0.3993(2) 0.0524(10) Uani 1 1 d . . . C55 C 0.6953(3) 0.1761(2) 0.4018(2) 0.0452(8) Uani 1 1 d . . . H55A H 0.6685 0.1785 0.4502 0.054 Uiso 1 1 calc R . . C56 C 0.7174(3) 0.0899(2) 0.3821(2) 0.0456(9) Uani 1 1 d . . . C57 C 0.7006(4) 0.0186(3) 0.4254(3) 0.0595(11) Uani 1 1 d . . . H57A H 0.6765 0.0216 0.4717 0.071 Uiso 1 1 calc R . . C58 C 0.7204(4) -0.0564(3) 0.3986(3) 0.0760(15) Uani 1 1 d . . . H58A H 0.7070 -0.1049 0.4261 0.091 Uiso 1 1 calc R . . C59 C 0.7593(4) -0.0596(3) 0.3325(3) 0.0771(15) Uani 1 1 d . . . H59A H 0.7739 -0.1103 0.3159 0.093 Uiso 1 1 calc R . . C60 C 0.7782(4) 0.0117(3) 0.2881(3) 0.0613(11) Uani 1 1 d . . . H60A H 0.8051 0.0087 0.2428 0.074 Uiso 1 1 calc R . . C61 C 0.7556(3) 0.0862(2) 0.3142(2) 0.0452(9) Uani 1 1 d . . . C62 C 0.3808(3) 0.2464(2) 0.13792(18) 0.0389(8) Uani 1 1 d . . . H62A H 0.4054 0.2414 0.0891 0.047 Uiso 1 1 calc R . . C63 C 0.3707(3) 0.3366(2) 0.1579(2) 0.0412(8) Uani 1 1 d . . . C64 C 0.3931(4) 0.4060(3) 0.1146(2) 0.0592(11) Uani 1 1 d . . . H64A H 0.4202 0.4020 0.0695 0.071 Uiso 1 1 calc R . . C65 C 0.3738(4) 0.4831(3) 0.1404(4) 0.0784(16) Uani 1 1 d . . . H65A H 0.3861 0.5304 0.1112 0.094 Uiso 1 1 calc R . . C66 C 0.3374(4) 0.4897(3) 0.2072(3) 0.0704(14) Uani 1 1 d . . . H66A H 0.3265 0.5418 0.2237 0.084 Uiso 1 1 calc R . . C67 C 0.3163(4) 0.4203(2) 0.2507(2) 0.0556(11) Uani 1 1 d . . . H67A H 0.2906 0.4252 0.2962 0.067 Uiso 1 1 calc R . . C68 C 0.3338(3) 0.3429(2) 0.22612(19) 0.0402(8) Uani 1 1 d . . . C69 C 0.3151(3) 0.2597(2) 0.26639(18) 0.0381(7) Uani 1 1 d . . . H69A H 0.2905 0.2646 0.3152 0.046 Uiso 1 1 calc R . . C70 C 0.2230(3) 0.1936(2) 0.2087(2) 0.0412(8) Uani 1 1 d . . . C71 C 0.1119(4) 0.1460(3) 0.2204(3) 0.0643(11) Uani 1 1 d . . . H71A H 0.0887 0.1493 0.2670 0.077 Uiso 1 1 calc R . . C72 C 0.0363(5) 0.0927(3) 0.1590(4) 0.0935(18) Uani 1 1 d . . . H72A H -0.0387 0.0606 0.1648 0.112 Uiso 1 1 calc R . . C73 C 0.0706(5) 0.0874(4) 0.0914(4) 0.0943(19) Uani 1 1 d . . . H73A H 0.0185 0.0518 0.0517 0.113 Uiso 1 1 calc R . . C74 C 0.1815(4) 0.1338(3) 0.0802(3) 0.0730(14) Uani 1 1 d . . . H74A H 0.2046 0.1291 0.0339 0.088 Uiso 1 1 calc R . . C75 C 0.2579(3) 0.1880(2) 0.13992(19) 0.0420(8) Uani 1 1 d . . . C76 C 0.6277(4) 0.1168(3) 0.1035(2) 0.0566(11) Uani 1 1 d . . . C77 C 0.6875(5) 0.1156(4) 0.0443(3) 0.0867(16) Uani 1 1 d . . . H77A H 0.7205 0.1658 0.0226 0.104 Uiso 1 1 calc R . . C78 C 0.6967(6) 0.0308(5) 0.0170(3) 0.102(2) Uani 1 1 d . . . H78A H 0.7345 0.0265 -0.0236 0.122 Uiso 1 1 calc R . . C79 C 0.6514(7) -0.0389(5) 0.0500(4) 0.105(2) Uani 1 1 d . . . H79A H 0.6576 -0.0919 0.0320 0.126 Uiso 1 1 calc R . . C80 C 0.5988(6) -0.0354(4) 0.1068(4) 0.1003(19) Uani 1 1 d . . . H80A H 0.5695 -0.0859 0.1290 0.120 Uiso 1 1 calc R . . C81 C 0.5847(4) 0.0393(3) 0.1352(3) 0.0692(12) Uani 1 1 d . . . H81A H 0.5460 0.0390 0.1761 0.083 Uiso 1 1 calc R . . C82 C 0.4638(3) 0.2183(2) 0.40987(19) 0.0383(8) Uani 1 1 d . . . Cl1 Cl 0.1161(3) 0.04351(19) 0.40161(13) 0.1071(10) Uani 0.617(4) 1 d P A 1 Cl2 Cl 0.1236(3) 0.19610(19) 0.4815(3) 0.1533(17) Uani 0.617(4) 1 d P A 1 C83 C 0.0453(8) 0.1119(12) 0.4681(14) 0.308(18) Uani 0.617(4) 1 d P A 1 H83A H -0.0338 0.1144 0.4429 0.370 Uiso 0.617(4) 1 calc PR A 1 H83B H 0.0386 0.0854 0.5155 0.370 Uiso 0.617(4) 1 calc PR A 1 Cl3 Cl 1.0822(4) 0.3381(6) -0.0029(2) 0.170(3) Uani 0.383(4) 1 d P A 2 Cl4 Cl 0.9308(4) 0.3212(5) 0.0999(3) 0.167(3) Uani 0.383(4) 1 d P A 2 C84 C 1.0496(16) 0.3328(16) 0.0860(7) 0.134(8) Uani 0.383(4) 1 d P A 2 H84A H 1.0790 0.2862 0.1086 0.160 Uiso 0.383(4) 1 calc PR A 2 H84B H 1.0977 0.3854 0.1147 0.160 Uiso 0.383(4) 1 calc PR A 2 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 0.0503(17) 0.0479(17) 0.0297(14) 0.0032(12) 0.0043(12) 0.0274(13) N2 0.078(2) 0.073(2) 0.0355(17) 0.0107(15) 0.0141(16) 0.0339(18) C1 0.0308(15) 0.0336(16) 0.0303(15) 0.0019(12) 0.0036(12) 0.0103(12) C2 0.0322(16) 0.0338(16) 0.0284(15) 0.0026(12) 0.0073(12) 0.0117(12) C3 0.0347(16) 0.0300(15) 0.0319(15) 0.0058(12) 0.0073(13) 0.0119(12) C4 0.0359(17) 0.0342(16) 0.0308(16) 0.0062(12) 0.0092(13) 0.0132(13) C5 0.0332(16) 0.0337(16) 0.0372(17) 0.0039(13) 0.0094(13) 0.0116(12) C6 0.0287(15) 0.0368(17) 0.0351(16) 0.0044(13) 0.0051(13) 0.0126(12) C7 0.0338(16) 0.0390(17) 0.0288(15) 0.0032(12) 0.0080(13) 0.0145(13) C8 0.0333(16) 0.0361(17) 0.0433(18) 0.0060(13) 0.0102(14) 0.0164(13) C9 0.045(2) 0.0437(19) 0.053(2) 0.0133(16) 0.0192(16) 0.0188(15) C10 0.039(2) 0.048(2) 0.089(3) 0.017(2) 0.018(2) 0.0094(16) C11 0.038(2) 0.051(2) 0.076(3) -0.0007(19) 0.0025(19) 0.0073(16) C12 0.0375(19) 0.048(2) 0.054(2) 0.0024(16) 0.0015(16) 0.0152(15) C13 0.0341(16) 0.0330(16) 0.0391(17) 0.0031(13) 0.0073(13) 0.0159(13) C14 0.0367(17) 0.0379(17) 0.0319(16) 0.0073(13) 0.0073(13) 0.0161(13) C15 0.0316(16) 0.0341(16) 0.0429(18) 0.0075(13) 0.0143(13) 0.0124(12) C16 0.046(2) 0.0373(18) 0.055(2) 0.0113(15) 0.0147(16) 0.0157(15) C17 0.059(2) 0.0321(19) 0.089(3) 0.0103(19) 0.024(2) 0.0145(16) C18 0.059(2) 0.039(2) 0.069(3) -0.0106(18) 0.016(2) 0.0122(17) C19 0.046(2) 0.046(2) 0.047(2) -0.0025(15) 0.0107(16) 0.0137(15) C20 0.0279(15) 0.0377(17) 0.0434(18) 0.0007(13) 0.0097(13) 0.0120(13) C21 0.0442(19) 0.0489(19) 0.0367(17) 0.0096(14) 0.0174(15) 0.0199(15) C22 0.0354(18) 0.0447(19) 0.050(2) -0.0005(15) 0.0138(15) 0.0158(14) C23 0.048(2) 0.064(3) 0.058(2) -0.0104(19) 0.0088(18) 0.0228(18) C24 0.057(3) 0.054(3) 0.091(4) -0.016(2) 0.008(2) 0.019(2) C25 0.055(2) 0.037(2) 0.096(3) 0.004(2) 0.018(2) 0.0145(17) C26 0.0364(18) 0.043(2) 0.068(2) 0.0136(17) 0.0169(17) 0.0132(15) C27 0.0302(16) 0.0404(18) 0.051(2) 0.0040(15) 0.0123(14) 0.0132(13) C28 0.0332(17) 0.0446(19) 0.0412(18) 0.0055(14) 0.0076(14) 0.0171(14) C29 0.0344(18) 0.0420(19) 0.064(2) 0.0018(16) 0.0153(16) 0.0144(14) C30 0.036(2) 0.059(2) 0.076(3) -0.008(2) 0.0042(19) 0.0129(17) C31 0.038(2) 0.054(3) 0.137(5) 0.007(3) 0.008(3) 0.0016(19) C32 0.049(3) 0.057(3) 0.131(5) 0.029(3) 0.029(3) 0.004(2) C33 0.052(3) 0.067(3) 0.103(4) 0.032(3) 0.035(2) 0.022(2) C34 0.0364(18) 0.0442(19) 0.065(2) 0.0127(17) 0.0243(17) 0.0165(15) C35 0.0317(16) 0.0439(18) 0.0351(17) 0.0076(14) 0.0042(13) 0.0142(13) C36 0.046(2) 0.0427(19) 0.0341(17) 0.0034(14) 0.0017(15) 0.0045(15) C37 0.069(3) 0.037(2) 0.050(2) 0.0028(16) 0.0123(19) 0.0003(17) C38 0.061(2) 0.040(2) 0.064(3) 0.0153(18) 0.005(2) 0.0111(17) C39 0.075(3) 0.059(2) 0.040(2) 0.0135(17) -0.0013(19) 0.023(2) C40 0.059(2) 0.047(2) 0.0352(18) 0.0002(14) -0.0028(16) 0.0230(17) C41 0.0467(19) 0.0401(18) 0.0351(18) 0.0079(13) 0.0105(15) 0.0199(14) N3 0.0542(18) 0.0629(19) 0.0375(16) 0.0114(14) 0.0201(14) 0.0301(15) N4 0.072(2) 0.067(2) 0.0345(17) -0.0003(14) 0.0146(15) 0.0321(17) C42 0.0418(18) 0.0368(17) 0.0315(16) 0.0072(12) 0.0130(14) 0.0163(13) C43 0.0426(18) 0.0329(16) 0.0306(16) 0.0037(12) 0.0107(13) 0.0164(13) C44 0.0399(17) 0.0346(16) 0.0346(16) 0.0025(12) 0.0112(14) 0.0158(13) C45 0.0432(18) 0.0338(16) 0.0280(15) 0.0035(12) 0.0084(13) 0.0153(13) C46 0.0414(18) 0.0379(17) 0.0357(17) 0.0075(13) 0.0105(14) 0.0174(14) C47 0.0403(18) 0.0364(17) 0.0360(17) 0.0073(13) 0.0125(14) 0.0172(13) C48 0.0422(19) 0.053(2) 0.046(2) 0.0086(16) 0.0130(16) 0.0237(16) C49 0.041(2) 0.052(2) 0.067(3) 0.0164(18) 0.0071(18) 0.0211(16) C50 0.047(2) 0.066(3) 0.097(3) 0.029(2) 0.010(2) 0.015(2) C51 0.057(3) 0.072(3) 0.137(6) 0.024(3) -0.009(4) 0.000(2) C52 0.057(3) 0.081(4) 0.124(5) -0.017(3) -0.015(3) 0.007(3) C53 0.071(3) 0.075(3) 0.074(3) -0.010(2) -0.013(2) 0.033(3) C54 0.048(2) 0.054(2) 0.057(2) 0.0018(17) -0.0010(18) 0.0225(17) C55 0.048(2) 0.057(2) 0.0358(18) 0.0083(15) 0.0082(15) 0.0234(17) C56 0.0376(18) 0.052(2) 0.052(2) 0.0154(16) 0.0069(16) 0.0222(15) C57 0.048(2) 0.065(3) 0.073(3) 0.028(2) 0.012(2) 0.0254(19) C58 0.061(3) 0.065(3) 0.110(4) 0.042(3) 0.018(3) 0.027(2) C59 0.071(3) 0.052(3) 0.114(4) 0.007(3) 0.006(3) 0.034(2) C60 0.057(2) 0.061(3) 0.077(3) 0.007(2) 0.014(2) 0.034(2) C61 0.0400(19) 0.051(2) 0.051(2) 0.0127(16) 0.0074(16) 0.0225(15) C62 0.0474(19) 0.0492(19) 0.0273(16) 0.0041(13) 0.0088(14) 0.0242(15) C63 0.0403(18) 0.0394(18) 0.0458(19) 0.0074(14) 0.0032(15) 0.0168(14) C64 0.058(2) 0.056(2) 0.063(3) 0.0231(19) 0.002(2) 0.0187(19) C65 0.074(3) 0.041(2) 0.110(4) 0.019(2) -0.013(3) 0.016(2) C66 0.078(3) 0.040(2) 0.088(3) -0.008(2) -0.015(3) 0.027(2) C67 0.063(2) 0.049(2) 0.056(2) -0.0122(18) -0.0083(19) 0.0321(18) C68 0.0414(18) 0.0409(18) 0.0393(18) -0.0023(14) -0.0026(15) 0.0199(14) C69 0.0441(18) 0.0463(19) 0.0317(16) 0.0009(13) 0.0094(14) 0.0245(15) C70 0.0426(19) 0.0405(18) 0.0442(19) 0.0001(14) 0.0099(15) 0.0165(14) C71 0.055(3) 0.061(3) 0.081(3) 0.004(2) 0.025(2) 0.014(2) C72 0.060(3) 0.077(3) 0.127(5) -0.028(3) 0.020(3) -0.011(3) C73 0.061(3) 0.092(4) 0.106(4) -0.053(3) 0.001(3) -0.009(3) C74 0.076(3) 0.085(3) 0.060(3) -0.027(2) 0.006(2) 0.032(3) C75 0.0460(19) 0.0427(19) 0.0402(18) -0.0044(14) 0.0046(15) 0.0199(15) C76 0.050(2) 0.087(3) 0.041(2) -0.0127(19) 0.0066(17) 0.036(2) C77 0.094(4) 0.146(5) 0.048(2) 0.006(3) 0.030(2) 0.070(3) C78 0.124(5) 0.142(6) 0.068(3) -0.012(4) 0.042(3) 0.072(4) C79 0.133(6) 0.106(5) 0.092(4) -0.013(4) 0.043(4) 0.047(4) C80 0.121(5) 0.068(3) 0.119(5) -0.020(3) 0.039(4) 0.029(3) C81 0.077(3) 0.053(3) 0.078(3) -0.013(2) 0.022(2) 0.012(2) C82 0.0460(19) 0.0395(18) 0.0334(17) 0.0004(13) 0.0046(14) 0.0204(14) Cl1 0.125(2) 0.142(2) 0.0667(14) 0.0103(13) 0.0054(13) 0.0664(18) Cl2 0.105(2) 0.0841(18) 0.275(5) 0.016(2) 0.008(2) 0.0510(16) C83 0.027(4) 0.31(2) 0.55(4) 0.36(3) -0.017(10) 0.001(8) Cl3 0.096(3) 0.394(10) 0.048(2) 0.037(3) 0.021(2) 0.108(5) Cl4 0.081(3) 0.314(9) 0.141(4) 0.091(5) 0.062(3) 0.082(4) C84 0.137(14) 0.29(2) 0.029(6) 0.014(9) 0.004(7) 0.157(17) _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 C1 1.405(4) . ? N1 C35 1.418(4) . ? N2 C41 1.147(4) . ? C1 C2 1.399(4) . ? C1 C6 1.398(5) . ? C2 C3 1.390(4) . ? C2 C7 1.534(4) . ? C3 C4 1.388(4) . ? C3 C14 1.522(4) . ? C4 C5 1.408(4) . ? C4 C41 1.430(4) . ? C5 C6 1.386(4) . ? C5 C21 1.513(5) . ? C6 C28 1.533(4) . ? C7 C20 1.508(4) . ? C7 C8 1.535(4) . ? C8 C9 1.374(5) . ? C8 C13 1.393(4) . ? C9 C10 1.388(5) . ? C10 C11 1.361(6) . ? C11 C12 1.407(5) . ? C12 C13 1.363(4) . ? C13 C14 1.534(4) . ? C14 C15 1.520(4) . ? C15 C16 1.372(5) . ? C15 C20 1.399(4) . ? C16 C17 1.410(6) . ? C17 C18 1.377(6) . ? C18 C19 1.394(5) . ? C19 C20 1.380(5) . ? C21 C34 1.512(5) . ? C21 C22 1.531(5) . ? C22 C27 1.368(5) . ? C22 C23 1.395(5) . ? C23 C24 1.378(6) . ? C24 C25 1.371(7) . ? C25 C26 1.384(6) . ? C26 C27 1.388(5) . ? C27 C28 1.536(5) . ? C28 C29 1.526(5) . ? C29 C34 1.369(5) . ? C29 C30 1.402(5) . ? C30 C31 1.379(7) . ? C31 C32 1.356(7) . ? C32 C33 1.378(7) . ? C33 C34 1.401(5) . ? C35 C36 1.355(5) . ? C35 C40 1.400(4) . ? C36 C37 1.380(5) . ? C37 C38 1.362(5) . ? C38 C39 1.373(6) . ? C39 C40 1.371(5) . ? N3 C42 1.396(4) . ? N3 C76 1.429(5) . ? N4 C82 1.149(4) . ? C42 C47 1.400(4) . ? C42 C43 1.399(5) . ? C43 C44 1.384(4) . ? C43 C62 1.512(4) . ? C44 C45 1.395(4) . ? C44 C69 1.528(4) . ? C45 C46 1.397(5) . ? C45 C82 1.424(5) . ? C46 C47 1.384(5) . ? C46 C55 1.523(4) . ? C47 C48 1.532(5) . ? C48 C61 1.528(5) . ? C48 C49 1.529(5) . ? C49 C54 1.383(6) . ? C49 C50 1.379(6) . ? C50 C51 1.399(8) . ? C51 C52 1.360(9) . ? C52 C53 1.417(8) . ? C53 C54 1.391(6) . ? C54 C55 1.527(5) . ? C55 C56 1.522(5) . ? C56 C61 1.380(5) . ? C56 C57 1.394(5) . ? C57 C58 1.378(7) . ? C58 C59 1.352(8) . ? C59 C60 1.406(7) . ? C60 C61 1.382(5) . ? C62 C75 1.521(5) . ? C62 C63 1.526(5) . ? C63 C64 1.374(5) . ? C63 C68 1.383(5) . ? C64 C65 1.400(7) . ? C65 C66 1.356(7) . ? C66 C67 1.376(6) . ? C67 C68 1.389(5) . ? C68 C69 1.523(5) . ? C69 C70 1.536(5) . ? C70 C75 1.378(5) . ? C70 C71 1.394(6) . ? C71 C72 1.406(7) . ? C72 C73 1.354(8) . ? C73 C74 1.382(8) . ? C74 C75 1.395(5) . ? C76 C77 1.379(6) . ? C76 C81 1.399(6) . ? C77 C78 1.477(8) . ? C78 C79 1.319(9) . ? C79 C80 1.291(9) . ? C80 C81 1.356(7) . ? Cl1 C83 2.02(3) . ? Cl2 C83 1.423(17) . ? Cl3 C84 1.709(14) . ? Cl4 C84 1.428(18) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 N1 C35 122.0(3) . . ? C2 C1 C6 118.3(3) . . ? C2 C1 N1 120.9(3) . . ? C6 C1 N1 120.8(3) . . ? C3 C2 C1 121.0(3) . . ? C3 C2 C7 112.3(3) . . ? C1 C2 C7 126.5(3) . . ? C4 C3 C2 120.3(3) . . ? C4 C3 C14 126.1(3) . . ? C2 C3 C14 113.6(3) . . ? C3 C4 C5 119.2(3) . . ? C3 C4 C41 121.6(3) . . ? C5 C4 C41 119.2(3) . . ? C6 C5 C4 120.0(3) . . ? C6 C5 C21 114.4(3) . . ? C4 C5 C21 125.6(3) . . ? C5 C6 C1 121.0(3) . . ? C5 C6 C28 112.0(3) . . ? C1 C6 C28 126.9(3) . . ? C20 C7 C8 105.1(2) . . ? C20 C7 C2 106.9(2) . . ? C8 C7 C2 105.5(2) . . ? C9 C8 C13 119.9(3) . . ? C9 C8 C7 127.0(3) . . ? C13 C8 C7 113.1(3) . . ? C8 C9 C10 119.3(3) . . ? C11 C10 C9 120.8(4) . . ? C10 C11 C12 120.3(3) . . ? C13 C12 C11 118.7(3) . . ? C12 C13 C8 121.0(3) . . ? C12 C13 C14 126.5(3) . . ? C8 C13 C14 112.5(3) . . ? C15 C14 C3 106.8(2) . . ? C15 C14 C13 105.4(3) . . ? C3 C14 C13 105.3(2) . . ? C16 C15 C20 121.2(3) . . ? C16 C15 C14 126.0(3) . . ? C20 C15 C14 112.7(3) . . ? C15 C16 C17 118.4(4) . . ? C18 C17 C16 120.6(3) . . ? C17 C18 C19 120.4(3) . . ? C20 C19 C18 119.5(3) . . ? C19 C20 C15 119.9(3) . . ? C19 C20 C7 126.8(3) . . ? C15 C20 C7 113.3(3) . . ? C34 C21 C5 104.8(3) . . ? C34 C21 C22 106.0(3) . . ? C5 C21 C22 105.3(3) . . ? C27 C22 C23 121.1(3) . . ? C27 C22 C21 113.5(3) . . ? C23 C22 C21 125.4(3) . . ? C24 C23 C22 118.4(4) . . ? C25 C24 C23 120.5(4) . . ? C24 C25 C26 121.4(4) . . ? C25 C26 C27 118.3(4) . . ? C22 C27 C26 120.4(3) . . ? C22 C27 C28 113.2(3) . . ? C26 C27 C28 126.4(3) . . ? C29 C28 C6 104.7(3) . . ? C29 C28 C27 105.5(3) . . ? C6 C28 C27 105.4(2) . . ? C34 C29 C30 121.2(3) . . ? C34 C29 C28 113.8(3) . . ? C30 C29 C28 124.9(4) . . ? C31 C30 C29 118.0(4) . . ? C32 C31 C30 121.0(4) . . ? C31 C32 C33 121.5(4) . . ? C32 C33 C34 118.7(5) . . ? C29 C34 C33 119.5(4) . . ? C29 C34 C21 113.3(3) . . ? C33 C34 C21 127.2(4) . . ? C36 C35 C40 118.4(3) . . ? C36 C35 N1 123.5(3) . . ? C40 C35 N1 118.1(3) . . ? C35 C36 C37 121.2(3) . . ? C38 C37 C36 120.6(3) . . ? C37 C38 C39 118.8(3) . . ? C40 C39 C38 121.0(3) . . ? C39 C40 C35 119.9(3) . . ? N2 C41 C4 177.8(4) . . ? C42 N3 C76 120.4(3) . . ? N3 C42 C47 120.1(3) . . ? N3 C42 C43 121.9(3) . . ? C47 C42 C43 118.0(3) . . ? C44 C43 C42 121.0(3) . . ? C44 C43 C62 112.8(3) . . ? C42 C43 C62 126.2(3) . . ? C43 C44 C45 120.6(3) . . ? C43 C44 C69 113.7(3) . . ? C45 C44 C69 125.7(3) . . ? C44 C45 C46 118.7(3) . . ? C44 C45 C82 121.8(3) . . ? C46 C45 C82 119.5(3) . . ? C47 C46 C45 120.5(3) . . ? C47 C46 C55 113.6(3) . . ? C45 C46 C55 125.9(3) . . ? C46 C47 C42 121.1(3) . . ? C46 C47 C48 112.8(3) . . ? C42 C47 C48 126.0(3) . . ? C61 C48 C47 105.4(3) . . ? C61 C48 C49 106.2(3) . . ? C47 C48 C49 105.0(3) . . ? C54 C49 C50 121.7(4) . . ? C54 C49 C48 112.9(3) . . ? C50 C49 C48 125.4(4) . . ? C49 C50 C51 117.4(5) . . ? C52 C51 C50 122.0(5) . . ? C51 C52 C53 120.7(5) . . ? C54 C53 C52 117.2(6) . . ? C49 C54 C53 121.1(4) . . ? C49 C54 C55 113.4(3) . . ? C53 C54 C55 125.5(4) . . ? C56 C55 C46 105.8(3) . . ? C56 C55 C54 105.8(3) . . ? C46 C55 C54 104.7(3) . . ? C61 C56 C57 120.6(4) . . ? C61 C56 C55 113.6(3) . . ? C57 C56 C55 125.8(4) . . ? C58 C57 C56 119.0(5) . . ? C59 C58 C57 120.3(4) . . ? C58 C59 C60 121.8(4) . . ? C61 C60 C59 117.8(5) . . ? C56 C61 C60 120.4(4) . . ? C56 C61 C48 113.0(3) . . ? C60 C61 C48 126.6(4) . . ? C43 C62 C75 107.2(3) . . ? C43 C62 C63 105.7(2) . . ? C75 C62 C63 104.6(3) . . ? C64 C63 C68 121.2(4) . . ? C64 C63 C62 126.1(4) . . ? C68 C63 C62 112.7(3) . . ? C63 C64 C65 118.2(5) . . ? C66 C65 C64 120.9(4) . . ? C65 C66 C67 120.8(4) . . ? C66 C67 C68 119.4(4) . . ? C63 C68 C67 119.5(3) . . ? C63 C68 C69 113.7(3) . . ? C67 C68 C69 126.9(3) . . ? C68 C69 C44 105.7(3) . . ? C68 C69 C70 104.2(2) . . ? C44 C69 C70 105.4(3) . . ? C75 C70 C71 121.4(3) . . ? C75 C70 C69 113.1(3) . . ? C71 C70 C69 125.5(4) . . ? C70 C71 C72 117.2(5) . . ? C73 C72 C71 121.4(5) . . ? C72 C73 C74 121.3(4) . . ? C73 C74 C75 118.7(5) . . ? C70 C75 C74 120.0(4) . . ? C70 C75 C62 113.4(3) . . ? C74 C75 C62 126.5(4) . . ? C77 C76 C81 118.4(4) . . ? C77 C76 N3 119.5(5) . . ? C81 C76 N3 122.1(4) . . ? C76 C77 C78 116.7(6) . . ? C79 C78 C77 120.2(5) . . ? C80 C79 C78 121.6(6) . . ? C79 C80 C81 122.5(6) . . ? C80 C81 C76 120.5(5) . . ? N4 C82 C45 177.1(4) . . ? Cl2 C83 Cl1 107.1(10) . . ? Cl4 C84 Cl3 122.8(9) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 2.194 _refine_diff_density_min -0.458 _refine_diff_density_rms 0.112 _database_code_depnum_ccdc_archive 'CCDC 945647'