Supplementary information (ESI) for Phys. Chem. Chem. Phys. This journal is (c) the Owner Societies 2008 data_global _journal_name_full Phys.Chem.Chem.Phys.(PCCP) _journal_coden_Cambridge 1326 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Jay Siegel' _publ_contact_author_email JSS@OCI.UZH.CH _publ_section_title ; Through-Space Interactions between Parallel-Offset Arenes at the van der Waals Distance: 1,8-diarylbiphenylene syntheses, structure and QM computations ; loop_ _publ_author_name 'Jay Siegel' 'Gerardo Aguirre' 'Rita Annunziata' 'Kim K Baldridge' 'Maurizio Benaglia' ; F.Cozzi ; 'Yongsak Sritana-Anant' # Attachment '3e_F.cif' data_fu _database_code_depnum_ccdc_archive 'CCDC 678682' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C28 H23 F' _chemical_formula_sum 'C28 H23 F' _chemical_formula_weight 378.46 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 2/c' _symmetry_space_group_name_Hall '-C 2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 10.1807(7) _cell_length_b 12.6858(12) _cell_length_c 17.0404(15) _cell_angle_alpha 90.00 _cell_angle_beta 106.996(7) _cell_angle_gamma 90.00 _cell_volume 2104.7(3) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 86 _cell_measurement_theta_min 5.00 _cell_measurement_theta_max 12.96 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.40 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.194 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 800 _exptl_absorpt_coefficient_mu 0.074 _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 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker P4' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 97 _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3520 _diffrn_reflns_av_R_equivalents 0.0132 _diffrn_reflns_av_sigmaI/netI 0.0213 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 3 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 1 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.50 _diffrn_reflns_theta_max 27.50 _reflns_number_total 2430 _reflns_number_gt 1407 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker SHELXTL' _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^)+(0.0802P)^2^+1.3655P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0032(10) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2430 _refine_ls_number_parameters 151 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1141 _refine_ls_R_factor_gt 0.0703 _refine_ls_wR_factor_ref 0.2266 _refine_ls_wR_factor_gt 0.1986 _refine_ls_goodness_of_fit_ref 1.043 _refine_ls_restrained_S_all 1.043 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.9193(2) 0.1659(2) 0.63447(12) 0.0703(7) Uani 1 1 d . . . C2 C 0.9683(2) 0.10668(18) 0.70404(12) 0.0643(6) Uani 1 1 d . . . C3 C 0.9686(2) -0.0048(2) 0.70439(14) 0.0728(7) Uani 1 1 d . . . C4 C 0.9212(3) -0.0623(3) 0.63432(18) 0.0968(10) Uani 1 1 d . . . H4A H 0.9216 -0.1357 0.6345 0.116 Uiso 1 1 calc R . . C5 C 0.8722(3) -0.0047(3) 0.56289(18) 0.1054(11) Uani 1 1 d . . . H5A H 0.8391 -0.0407 0.5135 0.126 Uiso 1 1 calc R . . C6 C 0.8705(3) 0.1032(3) 0.56184(15) 0.0934(9) Uani 1 1 d . . . H6A H 0.8360 0.1373 0.5117 0.112 Uiso 1 1 calc R . . C7 C 0.9159(2) 0.2828(2) 0.63432(13) 0.0741(7) Uani 1 1 d . A . C8 C 0.9981(3) 0.3405(3) 0.59731(16) 0.0916(9) Uani 1 1 d . . . H8A H 1.0531 0.3060 0.5704 0.110 Uiso 0.391(3) 1 calc PR A 1 C9 C 0.9971(3) 0.4493(3) 0.60086(19) 0.1053(10) Uani 1 1 d . A . H9A H 1.0544 0.4878 0.5779 0.126 Uiso 1 1 calc R . . C10 C 0.9129(3) 0.5016(3) 0.63782(19) 0.0994(10) Uani 1 1 d . . . C11 C 0.8304(3) 0.4461(2) 0.67293(18) 0.0935(9) Uani 1 1 d . A . H11A H 0.7729 0.4818 0.6974 0.112 Uiso 1 1 calc R . . C12 C 0.8314(2) 0.3365(2) 0.67245(15) 0.0769(7) Uani 1 1 d . . . H12A H 0.7760 0.2990 0.6974 0.092 Uiso 0.109(3) 1 calc PR A 1 C13 C 1.0850(5) 0.2788(4) 0.5499(3) 0.1008(16) Uani 0.609(3) 1 d P A 1 H13A H 1.1439 0.3270 0.5329 0.151 Uiso 0.609(3) 1 calc PR A 1 H13B H 1.0244 0.2452 0.5026 0.151 Uiso 0.609(3) 1 calc PR A 1 H13C H 1.1398 0.2263 0.5854 0.151 Uiso 0.609(3) 1 calc PR A 1 C14 C 0.7380(3) 0.2775(3) 0.7108(2) 0.0918(10) Uani 0.891(3) 1 d P A 1 H14A H 0.6811 0.2303 0.6712 0.138 Uiso 0.891(3) 1 calc PR A 1 H14B H 0.6811 0.3266 0.7288 0.138 Uiso 0.891(3) 1 calc PR A 1 H14C H 0.7920 0.2379 0.7570 0.138 Uiso 0.891(3) 1 calc PR A 1 C15 C 0.9151(16) 0.6231(12) 0.6526(10) 0.104(5) Uani 0.50 1 d P A 1 H15A H 0.8858 0.6377 0.7002 0.156 Uiso 0.50 1 calc PR A 1 H15B H 0.8541 0.6571 0.6057 0.156 Uiso 0.50 1 calc PR A 1 H15C H 1.0067 0.6493 0.6612 0.156 Uiso 0.50 1 calc PR A 1 F1 F 0.9139(14) 0.6125(10) 0.6395(8) 0.162(4) Uani 0.50 1 d P A 1 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0617(13) 0.0935(18) 0.0512(12) 0.0010(11) 0.0092(10) 0.0125(12) C2 0.0558(12) 0.0803(16) 0.0517(12) -0.0036(10) 0.0080(9) 0.0039(11) C3 0.0583(13) 0.0769(16) 0.0761(15) -0.0055(12) 0.0089(11) 0.0029(11) C4 0.0753(17) 0.095(2) 0.105(2) -0.0321(17) 0.0020(16) 0.0065(15) C5 0.094(2) 0.126(3) 0.080(2) -0.0356(19) 0.0007(16) 0.018(2) C6 0.0838(18) 0.134(3) 0.0507(13) -0.0050(14) 0.0014(12) 0.0210(17) C7 0.0661(14) 0.0987(19) 0.0532(12) 0.0155(12) 0.0109(10) 0.0147(13) C8 0.0897(19) 0.113(2) 0.0724(16) 0.0306(15) 0.0240(14) 0.0147(17) C9 0.100(2) 0.123(3) 0.092(2) 0.0384(19) 0.0258(17) 0.002(2) C10 0.098(2) 0.089(2) 0.099(2) 0.0195(17) 0.0100(18) 0.0071(18) C11 0.0750(17) 0.102(2) 0.097(2) 0.0123(17) 0.0138(15) 0.0199(16) C12 0.0635(14) 0.0899(19) 0.0730(15) 0.0151(13) 0.0130(12) 0.0122(13) C13 0.109(4) 0.115(4) 0.092(3) 0.005(3) 0.051(3) -0.003(3) C14 0.0736(18) 0.105(2) 0.103(2) 0.0076(18) 0.0361(17) 0.0133(17) C15 0.106(8) 0.084(9) 0.130(9) 0.050(8) 0.044(7) 0.015(6) F1 0.190(9) 0.095(5) 0.171(7) -0.017(4) 0.006(6) -0.012(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.369(3) . ? C1 C6 1.433(3) . ? C1 C7 1.483(4) . ? C2 C3 1.414(3) . ? C2 C2 1.510(4) 2_756 ? C3 C4 1.362(3) . ? C3 C3 1.498(5) 2_756 ? C4 C5 1.382(4) . ? C4 H4A 0.9300 . ? C5 C6 1.368(4) . ? C5 H5A 0.9300 . ? C6 H6A 0.9300 . ? C7 C8 1.393(4) . ? C7 C12 1.397(3) . ? C8 C9 1.383(4) . ? C8 C13 1.570(5) . ? C8 H8A 0.9300 . ? C9 C10 1.373(4) . ? C9 H9A 0.9300 . ? C10 C11 1.362(4) . ? C10 F1 1.407(12) . ? C10 C15 1.562(17) . ? C11 C12 1.390(4) . ? C11 H11A 0.9300 . ? C12 C14 1.502(4) . ? C12 H12A 0.9300 . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C6 112.9(2) . . ? C2 C1 C7 123.6(2) . . ? C6 C1 C7 123.5(2) . . ? C1 C2 C3 123.6(2) . . ? C1 C2 C2 146.68(14) . 2_756 ? C3 C2 C2 89.76(13) . 2_756 ? C4 C3 C2 122.2(2) . . ? C4 C3 C3 147.58(18) . 2_756 ? C2 C3 C3 90.24(13) . 2_756 ? C3 C4 C5 115.6(3) . . ? C3 C4 H4A 122.2 . . ? C5 C4 H4A 122.2 . . ? C6 C5 C4 122.7(3) . . ? C6 C5 H5A 118.6 . . ? C4 C5 H5A 118.6 . . ? C5 C6 C1 123.0(3) . . ? C5 C6 H6A 118.5 . . ? C1 C6 H6A 118.5 . . ? C8 C7 C12 119.2(3) . . ? C8 C7 C1 120.6(2) . . ? C12 C7 C1 120.3(2) . . ? C9 C8 C7 119.5(3) . . ? C9 C8 C13 122.2(3) . . ? C7 C8 C13 118.3(3) . . ? C9 C8 H8A 120.3 . . ? C7 C8 H8A 120.3 . . ? C10 C9 C8 121.0(3) . . ? C10 C9 H9A 119.5 . . ? C8 C9 H9A 119.5 . . ? C11 C10 C9 120.0(3) . . ? C11 C10 F1 120.7(6) . . ? C9 C10 F1 119.3(6) . . ? C11 C10 C15 114.9(6) . . ? C9 C10 C15 124.7(6) . . ? C10 C11 C12 120.5(3) . . ? C10 C11 H11A 119.7 . . ? C12 C11 H11A 119.7 . . ? C11 C12 C7 119.8(3) . . ? C11 C12 C14 119.3(3) . . ? C7 C12 C14 120.9(3) . . ? C11 C12 H12A 120.1 . . ? C7 C12 H12A 120.1 . . ? C8 C13 H13A 109.5 . . ? C8 C13 H13B 109.5 . . ? C8 C13 H13C 109.5 . . ? C12 C14 H14A 109.5 . . ? C12 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C12 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C10 C15 H15A 109.5 . . ? C10 C15 H15B 109.5 . . ? C10 C15 H15C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 -1.0(3) . . . . ? C7 C1 C2 C3 178.5(2) . . . . ? C6 C1 C2 C2 180.0(4) . . . 2_756 ? C7 C1 C2 C2 -0.6(6) . . . 2_756 ? C1 C2 C3 C4 0.9(4) . . . . ? C2 C2 C3 C4 -179.6(2) 2_756 . . . ? C1 C2 C3 C3 -179.4(2) . . . 2_756 ? C2 C2 C3 C3 0.0(2) 2_756 . . 2_756 ? C2 C3 C4 C5 -0.2(4) . . . . ? C3 C3 C4 C5 -179.6(5) 2_756 . . . ? C3 C4 C5 C6 -0.3(5) . . . . ? C4 C5 C6 C1 0.1(5) . . . . ? C2 C1 C6 C5 0.5(4) . . . . ? C7 C1 C6 C5 -179.0(3) . . . . ? C2 C1 C7 C8 113.3(3) . . . . ? C6 C1 C7 C8 -67.3(3) . . . . ? C2 C1 C7 C12 -65.7(3) . . . . ? C6 C1 C7 C12 113.6(3) . . . . ? C12 C7 C8 C9 1.7(4) . . . . ? C1 C7 C8 C9 -177.4(2) . . . . ? C12 C7 C8 C13 -176.1(3) . . . . ? C1 C7 C8 C13 4.8(4) . . . . ? C7 C8 C9 C10 -2.3(4) . . . . ? C13 C8 C9 C10 175.4(3) . . . . ? C8 C9 C10 C11 1.1(5) . . . . ? C8 C9 C10 F1 -179.4(6) . . . . ? C8 C9 C10 C15 173.6(7) . . . . ? C9 C10 C11 C12 0.6(4) . . . . ? F1 C10 C11 C12 -178.9(6) . . . . ? C15 C10 C11 C12 -172.5(7) . . . . ? C10 C11 C12 C7 -1.2(4) . . . . ? C10 C11 C12 C14 -179.3(3) . . . . ? C8 C7 C12 C11 0.0(3) . . . . ? C1 C7 C12 C11 179.1(2) . . . . ? C8 C7 C12 C14 178.1(2) . . . . ? C1 C7 C12 C14 -2.8(3) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.176 _refine_diff_density_min -0.172 _refine_diff_density_rms 0.029 # Attachment '3b_H.CIF' data_jesh _database_code_depnum_ccdc_archive 'CCDC 679270' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C28 H24' _chemical_formula_weight 360.47 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _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 8.2700(13) _cell_length_b 18.901(4) _cell_length_c 13.723(3) _cell_angle_alpha 90.00 _cell_angle_beta 103.554(15) _cell_angle_gamma 90.00 _cell_volume 2085.3(7) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 39 _cell_measurement_theta_min 4.73 _cell_measurement_theta_max 12.29 _exptl_crystal_description irregular _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.33 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.148 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 768 _exptl_absorpt_coefficient_mu 0.065 _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 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker P4' _diffrn_measurement_method '2\q/\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 97 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 6.35 _diffrn_reflns_number 3938 _diffrn_reflns_av_R_equivalents 0.0647 _diffrn_reflns_av_sigmaI/netI 0.0846 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.87 _diffrn_reflns_theta_max 24.99 _reflns_number_total 3670 _reflns_number_gt 1552 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.038(9) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3670 _refine_ls_number_parameters 234 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.2725 _refine_ls_R_factor_gt 0.1637 _refine_ls_wR_factor_ref 0.4190 _refine_ls_wR_factor_gt 0.3833 _refine_ls_goodness_of_fit_ref 1.901 _refine_ls_restrained_S_all 1.912 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.0209(8) 0.1384(4) 0.0999(5) 0.068(2) Uani 1 1 d . . . C2 C -0.0459(10) 0.1455(4) -0.0032(6) 0.091(3) Uani 1 1 d . . . H2A H -0.1335 0.1772 -0.0227 0.110 Uiso 1 1 calc R . . C3 C 0.0033(14) 0.1112(5) -0.0765(6) 0.119(3) Uani 1 1 d . . . H3A H -0.0514 0.1186 -0.1431 0.143 Uiso 1 1 calc R . . C4 C 0.1413(12) 0.0629(5) -0.0520(6) 0.115(3) Uani 1 1 d . . . H4A H 0.1805 0.0389 -0.1009 0.138 Uiso 1 1 calc R . . C5 C 0.2095(10) 0.0547(4) 0.0458(6) 0.091(2) Uani 1 1 d . . . C6 C 0.3368(10) 0.0171(5) 0.1258(6) 0.095(3) Uani 1 1 d . . . C7 C 0.4598(11) -0.0303(5) 0.1474(8) 0.116(3) Uani 1 1 d . . . H7A H 0.4976 -0.0542 0.0978 0.139 Uiso 1 1 calc R . . C8 C 0.5277(10) -0.0417(5) 0.2491(9) 0.114(3) Uani 1 1 d . . . H8A H 0.6154 -0.0735 0.2674 0.137 Uiso 1 1 calc R . . C9 C 0.4720(10) -0.0085(4) 0.3228(7) 0.098(3) Uani 1 1 d . . . H9A H 0.5221 -0.0186 0.3894 0.118 Uiso 1 1 calc R . . C10 C 0.3385(9) 0.0414(4) 0.3009(5) 0.077(2) Uani 1 1 d . . . C11 C 0.2785(8) 0.0525(4) 0.2007(6) 0.080(2) Uani 1 1 d . . . C12 C 0.1492(9) 0.0916(4) 0.1202(5) 0.075(2) Uani 1 1 d . . . C13 C -0.0483(8) 0.1759(3) 0.1748(3) 0.075(2) Uani 1 1 d G . . C14 C -0.2091(7) 0.1612(3) 0.1833(5) 0.156(5) Uani 1 1 d G . . H14A H -0.2738 0.1286 0.1405 0.187 Uiso 1 1 calc R . . C15 C -0.2730(8) 0.1951(5) 0.2560(6) 0.182(6) Uani 1 1 d G . . H15A H -0.3806 0.1853 0.2617 0.219 Uiso 1 1 calc R . . C16 C -0.1762(13) 0.2439(4) 0.3200(4) 0.200(8) Uani 1 1 d G . . H16A H -0.2190 0.2666 0.3686 0.240 Uiso 1 1 calc R . . C17 C -0.0155(12) 0.2586(3) 0.3115(4) 0.177(7) Uani 1 1 d G . . H17A H 0.0493 0.2912 0.3544 0.212 Uiso 1 1 calc R . . C18 C 0.0485(7) 0.2247(3) 0.2389(5) 0.101(3) Uani 1 1 d GD . . C19 C 0.2678(8) 0.0745(3) 0.3817(4) 0.080(2) Uani 1 1 d G . . C20 C 0.1036(8) 0.0597(3) 0.3828(4) 0.095(3) Uani 1 1 d GD . . C21 C 0.0318(8) 0.0914(4) 0.4539(6) 0.145(4) Uani 1 1 d G . . H21A H -0.0780 0.0815 0.4546 0.174 Uiso 1 1 calc R . . C22 C 0.1243(13) 0.1378(4) 0.5238(4) 0.149(5) Uani 1 1 d GD . . C23 C 0.2885(13) 0.1526(3) 0.5227(4) 0.139(5) Uani 1 1 d G . . H23A H 0.3503 0.1837 0.5695 0.167 Uiso 1 1 calc R . . C24 C 0.3602(8) 0.1210(3) 0.4516(5) 0.133(4) Uani 1 1 d GD . . C26 C 0.0013(10) 0.0073(5) 0.3145(6) 0.132(4) Uani 1 1 d D . . H26A H -0.1056 0.0031 0.3300 0.198 Uiso 1 1 calc R . . H26B H 0.0561 -0.0378 0.3229 0.198 Uiso 1 1 calc R . . H26C H -0.0128 0.0227 0.2463 0.198 Uiso 1 1 calc R . . C28 C 0.5337(11) 0.1403(7) 0.4644(9) 0.188(6) Uani 1 1 d D . . H28A H 0.5709 0.1654 0.5265 0.283 Uiso 1 1 calc R . . H28B H 0.5456 0.1701 0.4098 0.283 Uiso 1 1 calc R . . H28C H 0.5993 0.0984 0.4652 0.283 Uiso 1 1 calc R . . C25 C 0.2257(11) 0.2420(5) 0.2329(7) 0.166(5) Uani 1 1 d D . . H25A H 0.2625 0.2839 0.2712 0.248 Uiso 1 1 calc R . . H25B H 0.2288 0.2498 0.1642 0.248 Uiso 1 1 calc R . . H25C H 0.2976 0.2032 0.2594 0.248 Uiso 1 1 calc R . . C27 C 0.0261(16) 0.1695(8) 0.5945(9) 0.254(8) Uani 1 1 d D . . H27A H 0.0513 0.2189 0.6037 0.381 Uiso 1 1 calc R . . H27B H 0.0560 0.1458 0.6581 0.381 Uiso 1 1 calc R . . H27C H -0.0908 0.1636 0.5663 0.381 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 C1 0.044(4) 0.086(5) 0.070(5) -0.005(4) 0.004(3) -0.002(4) C2 0.104(7) 0.108(6) 0.062(5) 0.010(4) 0.021(5) 0.034(5) C3 0.157(9) 0.129(8) 0.067(5) 0.009(6) 0.020(6) 0.015(7) C4 0.138(8) 0.143(8) 0.069(6) 0.002(5) 0.034(5) 0.039(7) C5 0.079(5) 0.113(7) 0.080(6) -0.005(5) 0.019(5) 0.017(5) C6 0.082(6) 0.116(7) 0.092(6) 0.001(5) 0.033(5) 0.033(6) C7 0.090(7) 0.134(8) 0.126(8) 0.002(7) 0.031(6) 0.036(6) C8 0.076(6) 0.125(8) 0.130(8) 0.011(7) 0.000(6) 0.033(5) C9 0.074(6) 0.103(7) 0.105(7) 0.009(5) -0.005(5) 0.022(5) C10 0.070(5) 0.078(5) 0.076(5) 0.016(4) 0.000(4) -0.018(4) C11 0.059(5) 0.091(6) 0.084(5) 0.008(5) 0.006(4) 0.007(4) C12 0.066(5) 0.086(5) 0.068(5) 0.003(4) 0.003(4) 0.004(4) C13 0.103(6) 0.062(5) 0.065(4) 0.000(4) 0.027(4) 0.015(4) C14 0.177(10) 0.167(9) 0.175(10) 0.074(8) 0.145(9) 0.106(9) C15 0.184(12) 0.198(14) 0.197(14) 0.043(11) 0.110(11) 0.067(11) C16 0.240(17) 0.228(16) 0.139(12) 0.024(11) 0.059(12) 0.165(15) C17 0.34(2) 0.088(7) 0.082(7) -0.031(5) 0.000(9) 0.103(10) C18 0.127(8) 0.070(6) 0.090(6) 0.015(5) -0.004(6) 0.012(6) C19 0.116(7) 0.065(5) 0.051(4) 0.005(4) 0.006(5) -0.005(5) C20 0.097(7) 0.118(7) 0.072(6) 0.020(5) 0.023(5) 0.027(6) C21 0.222(12) 0.133(9) 0.096(7) 0.002(7) 0.069(8) 0.038(9) C22 0.234(15) 0.122(10) 0.095(9) 0.005(7) 0.043(10) 0.071(10) C23 0.255(16) 0.078(6) 0.067(6) -0.005(5) 0.003(8) -0.009(9) C24 0.206(12) 0.093(7) 0.068(6) 0.011(5) -0.032(7) -0.011(8) C26 0.097(7) 0.206(11) 0.097(7) -0.011(7) 0.033(5) -0.044(7) C28 0.146(11) 0.205(12) 0.188(12) 0.035(10) -0.012(9) -0.070(10) C25 0.211(12) 0.107(8) 0.143(9) 0.015(7) -0.031(9) -0.044(8) C27 0.289(19) 0.271(18) 0.191(14) -0.021(14) 0.034(14) -0.050(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 C1 C12 1.358(9) . ? C1 C2 1.400(9) . ? C1 C13 1.471(8) . ? C2 C3 1.337(10) . ? C2 H2A 0.9300 . ? C3 C4 1.439(11) . ? C3 H3A 0.9300 . ? C4 C5 1.337(10) . ? C4 H4A 0.9300 . ? C5 C12 1.419(10) . ? C5 C6 1.509(11) . ? C6 C7 1.335(10) . ? C6 C11 1.404(10) . ? C7 C8 1.393(11) . ? C7 H7A 0.9300 . ? C8 C9 1.359(11) . ? C8 H8A 0.9300 . ? C9 C10 1.430(10) . ? C9 H9A 0.9300 . ? C10 C11 1.363(9) . ? C10 C19 1.506(9) . ? C11 C12 1.536(9) . ? C13 C14 1.3900 . ? C13 C18 1.3900 . ? C14 C15 1.3900 . ? C14 H14A 0.9300 . ? C15 C16 1.3900 . ? C15 H15A 0.9300 . ? C16 C17 1.3900 . ? C16 H16A 0.9300 . ? C17 C18 1.3900 . ? C17 H17A 0.9300 . ? C18 C25 1.523(8) . ? C19 C20 1.3900 . ? C19 C24 1.3900 . ? C20 C21 1.3900 . ? C20 C26 1.486(7) . ? C21 C22 1.3900 . ? C21 H21A 0.9300 . ? C22 C23 1.3900 . ? C22 C27 1.526(9) . ? C23 C24 1.3900 . ? C23 H23A 0.9300 . ? C24 C28 1.450(8) . ? C26 H26A 0.9600 . ? C26 H26B 0.9600 . ? C26 H26C 0.9600 . ? C28 H28A 0.9600 . ? C28 H28B 0.9600 . ? C28 H28C 0.9600 . ? C25 H25A 0.9600 . ? C25 H25B 0.9600 . ? C25 H25C 0.9600 . ? C27 H27A 0.9600 . ? C27 H27B 0.9600 . ? C27 H27C 0.9600 . ? 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 C12 C1 C2 112.0(7) . . ? C12 C1 C13 125.7(6) . . ? C2 C1 C13 122.2(6) . . ? C3 C2 C1 126.6(8) . . ? C3 C2 H2A 116.7 . . ? C1 C2 H2A 116.7 . . ? C2 C3 C4 119.7(8) . . ? C2 C3 H3A 120.1 . . ? C4 C3 H3A 120.1 . . ? C5 C4 C3 115.7(8) . . ? C5 C4 H4A 122.2 . . ? C3 C4 H4A 122.2 . . ? C4 C5 C12 121.9(8) . . ? C4 C5 C6 147.4(8) . . ? C12 C5 C6 90.7(6) . . ? C7 C6 C11 122.1(8) . . ? C7 C6 C5 147.5(8) . . ? C11 C6 C5 90.4(6) . . ? C6 C7 C8 115.7(9) . . ? C6 C7 H7A 122.2 . . ? C8 C7 H7A 122.2 . . ? C9 C8 C7 123.2(9) . . ? C9 C8 H8A 118.4 . . ? C7 C8 H8A 118.4 . . ? C8 C9 C10 121.8(8) . . ? C8 C9 H9A 119.1 . . ? C10 C9 H9A 119.1 . . ? C11 C10 C9 113.3(8) . . ? C11 C10 C19 124.5(7) . . ? C9 C10 C19 122.2(7) . . ? C10 C11 C6 123.9(7) . . ? C10 C11 C12 145.8(7) . . ? C6 C11 C12 90.2(6) . . ? C1 C12 C5 124.1(7) . . ? C1 C12 C11 147.1(7) . . ? C5 C12 C11 88.7(6) . . ? C14 C13 C18 120.0 . . ? C14 C13 C1 119.9(5) . . ? C18 C13 C1 120.1(5) . . ? C15 C14 C13 120.0 . . ? C15 C14 H14A 120.0 . . ? C13 C14 H14A 120.0 . . ? C14 C15 C16 120.0 . . ? C14 C15 H15A 120.0 . . ? C16 C15 H15A 120.0 . . ? C17 C16 C15 120.0 . . ? C17 C16 H16A 120.0 . . ? C15 C16 H16A 120.0 . . ? C16 C17 C18 120.0 . . ? C16 C17 H17A 120.0 . . ? C18 C17 H17A 120.0 . . ? C17 C18 C13 120.0 . . ? C17 C18 C25 118.2(6) . . ? C13 C18 C25 121.8(6) . . ? C20 C19 C24 120.0 . . ? C20 C19 C10 118.3(5) . . ? C24 C19 C10 121.7(5) . . ? C21 C20 C19 120.0 . . ? C21 C20 C26 117.1(6) . . ? C19 C20 C26 122.7(6) . . ? C20 C21 C22 120.0 . . ? C20 C21 H21A 120.0 . . ? C22 C21 H21A 120.0 . . ? C23 C22 C21 120.0 . . ? C23 C22 C27 126.5(8) . . ? C21 C22 C27 113.5(8) . . ? C24 C23 C22 120.0 . . ? C24 C23 H23A 120.0 . . ? C22 C23 H23A 120.0 . . ? C23 C24 C19 120.0 . . ? C23 C24 C28 112.3(8) . . ? C19 C24 C28 127.6(8) . . ? C20 C26 H26A 109.5 . . ? C20 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C20 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C24 C28 H28A 109.5 . . ? C24 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C24 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? C18 C25 H25A 109.5 . . ? C18 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C18 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? C22 C27 H27A 109.5 . . ? C22 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C22 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C12 C1 C2 C3 0.9(12) . . . . ? C13 C1 C2 C3 -176.8(8) . . . . ? C1 C2 C3 C4 -1.9(14) . . . . ? C2 C3 C4 C5 1.4(13) . . . . ? C3 C4 C5 C12 -0.1(13) . . . . ? C3 C4 C5 C6 176.4(12) . . . . ? C4 C5 C6 C7 1(2) . . . . ? C12 C5 C6 C7 178.3(13) . . . . ? C4 C5 C6 C11 -176.6(14) . . . . ? C12 C5 C6 C11 0.4(6) . . . . ? C11 C6 C7 C8 -0.7(13) . . . . ? C5 C6 C7 C8 -178.2(12) . . . . ? C6 C7 C8 C9 1.4(14) . . . . ? C7 C8 C9 C10 -0.4(14) . . . . ? C8 C9 C10 C11 -1.3(11) . . . . ? C8 C9 C10 C19 175.5(8) . . . . ? C9 C10 C11 C6 2.1(10) . . . . ? C19 C10 C11 C6 -174.7(7) . . . . ? C9 C10 C11 C12 178.3(9) . . . . ? C19 C10 C11 C12 1.5(15) . . . . ? C7 C6 C11 C10 -1.1(13) . . . . ? C5 C6 C11 C10 177.5(7) . . . . ? C7 C6 C11 C12 -179.0(8) . . . . ? C5 C6 C11 C12 -0.4(6) . . . . ? C2 C1 C12 C5 0.5(10) . . . . ? C13 C1 C12 C5 178.1(7) . . . . ? C2 C1 C12 C11 -177.0(10) . . . . ? C13 C1 C12 C11 0.6(15) . . . . ? C4 C5 C12 C1 -0.9(13) . . . . ? C6 C5 C12 C1 -179.0(7) . . . . ? C4 C5 C12 C11 177.7(8) . . . . ? C6 C5 C12 C11 -0.4(6) . . . . ? C10 C11 C12 C1 1(2) . . . . ? C6 C11 C12 C1 178.3(11) . . . . ? C10 C11 C12 C5 -176.5(11) . . . . ? C6 C11 C12 C5 0.4(6) . . . . ? C12 C1 C13 C14 -113.2(7) . . . . ? C2 C1 C13 C14 64.1(8) . . . . ? C12 C1 C13 C18 64.9(8) . . . . ? C2 C1 C13 C18 -117.8(6) . . . . ? C18 C13 C14 C15 0.0 . . . . ? C1 C13 C14 C15 178.1(5) . . . . ? C13 C14 C15 C16 0.0 . . . . ? C14 C15 C16 C17 0.0 . . . . ? C15 C16 C17 C18 0.0 . . . . ? C16 C17 C18 C13 0.0 . . . . ? C16 C17 C18 C25 -179.5(6) . . . . ? C14 C13 C18 C17 0.0 . . . . ? C1 C13 C18 C17 -178.1(5) . . . . ? C14 C13 C18 C25 179.5(6) . . . . ? C1 C13 C18 C25 1.3(7) . . . . ? C11 C10 C19 C20 61.0(8) . . . . ? C9 C10 C19 C20 -115.5(6) . . . . ? C11 C10 C19 C24 -116.5(6) . . . . ? C9 C10 C19 C24 67.0(7) . . . . ? C24 C19 C20 C21 0.0 . . . . ? C10 C19 C20 C21 -177.6(5) . . . . ? C24 C19 C20 C26 -176.0(6) . . . . ? C10 C19 C20 C26 6.4(7) . . . . ? C19 C20 C21 C22 0.0 . . . . ? C26 C20 C21 C22 176.2(6) . . . . ? C20 C21 C22 C23 0.0 . . . . ? C20 C21 C22 C27 178.4(8) . . . . ? C21 C22 C23 C24 0.0 . . . . ? C27 C22 C23 C24 -178.2(9) . . . . ? C22 C23 C24 C19 0.0 . . . . ? C22 C23 C24 C28 -177.7(7) . . . . ? C20 C19 C24 C23 0.0 . . . . ? C10 C19 C24 C23 177.5(5) . . . . ? C20 C19 C24 C28 177.3(8) . . . . ? C10 C19 C24 C28 -5.2(8) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.738 _refine_diff_density_min -0.300 _refine_diff_density_rms 0.083 # Attachment '3c_Cl.CIF' data_gahj2 _database_code_depnum_ccdc_archive 'CCDC 679271' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C28 H23 Cl' _chemical_formula_weight 394.91 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' Cl Cl 0.1484 0.1585 '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 8.084(3) _cell_length_b 15.976(5) _cell_length_c 32.417(7) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 4187(2) _cell_formula_units_Z 8 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 65 _cell_measurement_theta_min 4.74 _cell_measurement_theta_max 11.32 _exptl_crystal_description Plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.253 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1664 _exptl_absorpt_coefficient_mu 0.194 _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 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker P4' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 97 _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3587 _diffrn_reflns_av_R_equivalents 0.0588 _diffrn_reflns_av_sigmaI/netI 0.0663 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 1 _diffrn_reflns_limit_k_min -1 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -34 _diffrn_reflns_limit_l_max 1 _diffrn_reflns_theta_min 2.51 _diffrn_reflns_theta_max 22.51 _reflns_number_total 2738 _reflns_number_gt 1527 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker SHELXTL' _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^)+(0.0897P)^2^+1.1405P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2738 _refine_ls_number_parameters 266 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1278 _refine_ls_R_factor_gt 0.0644 _refine_ls_wR_factor_ref 0.1881 _refine_ls_wR_factor_gt 0.1571 _refine_ls_goodness_of_fit_ref 1.016 _refine_ls_restrained_S_all 1.016 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl 0.9994(2) 0.36214(11) 0.19307(5) 0.1168(7) Uani 1 1 d . . . C28 C 0.4340(5) 0.5919(3) 0.06876(13) 0.0476(11) Uani 1 1 d . . . C27 C 0.3724(5) 0.6361(3) 0.14932(13) 0.0456(11) Uani 1 1 d . . . C26 C 0.3689(5) 0.6304(3) 0.10269(13) 0.0461(11) Uani 1 1 d . . . C25 C 0.5646(5) 0.5272(3) 0.06996(12) 0.0456(11) Uani 1 1 d . . . C24 C 0.3610(6) 0.6180(3) 0.03130(14) 0.0606(13) Uani 1 1 d . . . H24A H 0.3992 0.5952 0.0067 0.073 Uiso 1 1 calc R . . C23 C 0.3683(6) 0.6407(3) 0.22119(14) 0.0606(13) Uani 1 1 d . . . H23A H 0.4083 0.6235 0.2467 0.073 Uiso 1 1 calc R . . C20 C 0.5345(5) 0.4511(3) 0.09014(12) 0.0475(11) Uani 1 1 d . . . C22 C 0.5854(6) 0.5503(3) 0.18697(13) 0.0529(12) Uani 1 1 d . . . C21 C 0.4445(6) 0.6080(3) 0.18484(14) 0.0536(12) Uani 1 1 d . . . C19 C 0.2378(5) 0.6887(3) 0.10139(14) 0.0499(11) Uani 1 1 d . . . C18 C 0.9522(5) 0.3384(3) 0.07915(14) 0.0573(13) Uani 1 1 d . . . H18A H 0.9060 0.2832 0.0772 0.086 Uiso 1 1 calc R . . H18B H 1.0077 0.3445 0.1052 0.086 Uiso 1 1 calc R . . H18C H 1.0298 0.3469 0.0571 0.086 Uiso 1 1 calc R . . C17 C 0.1727(5) 0.7255(3) 0.18285(16) 0.0614(14) Uani 1 1 d . . . H17A H 0.0869 0.7643 0.1823 0.074 Uiso 1 1 calc R . . C16 C 0.8405(6) 0.4789(3) 0.05570(13) 0.0583(13) Uani 1 1 d . . . H16A H 0.9444 0.4886 0.0444 0.070 Uiso 1 1 calc R . . C15 C 0.7199(6) 0.5401(3) 0.05168(13) 0.0515(12) Uani 1 1 d . . . C14 C 0.7368(6) 0.5688(3) 0.16904(13) 0.0549(12) Uani 1 1 d . . . C13 C 0.8124(6) 0.4038(3) 0.07594(13) 0.0519(12) Uani 1 1 d . . . C12 C 0.2403(7) 0.6955(3) 0.22016(15) 0.0674(14) Uani 1 1 d . . . H12A H 0.1954 0.7141 0.2449 0.081 Uiso 1 1 calc R . . C11 C 0.6584(6) 0.3916(3) 0.09238(13) 0.0532(12) Uani 1 1 d . . . H11A H 0.6361 0.3412 0.1056 0.064 Uiso 1 1 calc R . . C10 C 0.2341(6) 0.6765(3) 0.02998(15) 0.0704(15) Uani 1 1 d . . . H10A H 0.1911 0.6918 0.0045 0.085 Uiso 1 1 calc R . . C9 C 0.8651(6) 0.5106(4) 0.17158(14) 0.0663(14) Uani 1 1 d . . . H9A H 0.9675 0.5228 0.1600 0.080 Uiso 1 1 calc R . . C8 C 0.2406(6) 0.6943(3) 0.14783(14) 0.0517(12) Uani 1 1 d . . . C7 C 0.1687(6) 0.7133(3) 0.06551(16) 0.0634(14) Uani 1 1 d . . . H7A H 0.0832 0.7521 0.0645 0.076 Uiso 1 1 calc R . . C6 C 0.8405(8) 0.4353(4) 0.19118(16) 0.0742(16) Uani 1 1 d . . . C5 C 0.5657(7) 0.4743(4) 0.20755(15) 0.0751(15) Uani 1 1 d . . . H5A H 0.4653 0.4621 0.2202 0.090 Uiso 1 1 calc R . . C4 C 0.7669(6) 0.6515(3) 0.14803(15) 0.0717(15) Uani 1 1 d . . . H4A H 0.6980 0.6557 0.1240 0.108 Uiso 1 1 calc R . . H4B H 0.8810 0.6554 0.1400 0.108 Uiso 1 1 calc R . . H4C H 0.7409 0.6963 0.1667 0.108 Uiso 1 1 calc R . . C3 C 0.6914(9) 0.4176(4) 0.20934(16) 0.0861(18) Uani 1 1 d . . . H3A H 0.6761 0.3669 0.2229 0.103 Uiso 1 1 calc R . . C2 C 0.7587(6) 0.6191(3) 0.02880(15) 0.0790(16) Uani 1 1 d . . . H2A H 0.8742 0.6202 0.0220 0.119 Uiso 1 1 calc R . . H2B H 0.7326 0.6665 0.0458 0.119 Uiso 1 1 calc R . . H2C H 0.6943 0.6213 0.0040 0.119 Uiso 1 1 calc R . . C1 C 0.3668(6) 0.4320(3) 0.10832(16) 0.0773(16) Uani 1 1 d . . . H1A H 0.2821 0.4480 0.0891 0.116 Uiso 1 1 calc R . . H1B H 0.3530 0.4626 0.1336 0.116 Uiso 1 1 calc R . . H1C H 0.3586 0.3731 0.1138 0.116 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.1322(15) 0.1263(14) 0.0920(11) -0.0161(10) -0.0289(10) 0.0637(12) C28 0.048(3) 0.046(3) 0.048(3) 0.000(2) -0.004(2) -0.004(2) C27 0.044(3) 0.045(3) 0.047(3) -0.003(2) 0.002(2) -0.001(2) C26 0.045(3) 0.044(3) 0.050(3) -0.002(2) -0.003(2) -0.006(2) C25 0.049(3) 0.046(3) 0.042(3) -0.008(2) -0.003(2) 0.001(3) C24 0.073(3) 0.056(3) 0.053(3) -0.008(2) -0.010(3) 0.006(3) C23 0.061(3) 0.069(3) 0.051(3) -0.006(3) 0.005(3) -0.005(3) C20 0.053(3) 0.044(3) 0.045(3) -0.005(2) -0.005(2) -0.006(3) C22 0.058(3) 0.059(3) 0.042(3) 0.000(2) -0.003(2) 0.003(3) C21 0.056(3) 0.052(3) 0.053(3) -0.003(2) 0.002(3) -0.012(3) C19 0.046(3) 0.042(3) 0.061(3) -0.005(2) -0.007(3) 0.005(3) C18 0.063(3) 0.051(3) 0.058(3) -0.008(2) -0.019(2) 0.024(3) C17 0.043(3) 0.059(3) 0.082(4) -0.019(3) 0.008(3) -0.002(3) C16 0.049(3) 0.073(4) 0.053(3) -0.014(3) 0.006(2) 0.001(3) C15 0.059(3) 0.049(3) 0.047(3) -0.005(2) 0.003(2) -0.002(3) C14 0.057(3) 0.063(3) 0.045(3) -0.005(2) -0.006(3) -0.008(3) C13 0.059(3) 0.052(3) 0.045(3) -0.008(2) -0.007(2) 0.002(3) C12 0.064(3) 0.079(4) 0.059(4) -0.016(3) 0.007(3) -0.012(3) C11 0.068(3) 0.037(3) 0.054(3) 0.000(2) -0.008(3) -0.001(3) C10 0.085(4) 0.070(4) 0.057(3) -0.005(3) -0.025(3) 0.011(3) C9 0.060(3) 0.089(4) 0.051(3) -0.015(3) -0.007(3) 0.010(3) C8 0.046(3) 0.048(3) 0.062(3) -0.009(2) 0.006(3) -0.004(3) C7 0.061(3) 0.049(3) 0.079(4) -0.007(3) -0.020(3) 0.012(3) C6 0.083(4) 0.083(4) 0.056(3) -0.006(3) -0.016(3) 0.024(4) C5 0.080(4) 0.080(4) 0.065(3) 0.018(3) 0.010(3) 0.015(4) C4 0.059(3) 0.082(4) 0.075(3) -0.003(3) 0.002(3) -0.015(3) C3 0.111(5) 0.073(4) 0.074(4) 0.018(3) -0.004(4) 0.015(4) C2 0.080(4) 0.074(4) 0.083(4) 0.019(3) 0.021(3) 0.000(3) C1 0.069(3) 0.060(3) 0.103(4) 0.003(3) 0.007(3) -0.008(3) _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 Cl1 C6 1.738(5) . ? C28 C26 1.366(5) . ? C28 C24 1.413(6) . ? C28 C25 1.477(6) . ? C27 C21 1.366(6) . ? C27 C8 1.415(6) . ? C27 C26 1.514(6) . ? C26 C19 1.411(6) . ? C25 C20 1.402(6) . ? C25 C15 1.404(6) . ? C24 C10 1.388(6) . ? C24 H24A 0.9300 . ? C23 C12 1.357(6) . ? C23 C21 1.428(6) . ? C23 H23A 0.9300 . ? C20 C11 1.383(6) . ? C20 C1 1.510(6) . ? C22 C14 1.387(6) . ? C22 C5 1.394(6) . ? C22 C21 1.468(6) . ? C19 C7 1.348(6) . ? C19 C8 1.508(6) . ? C18 C13 1.542(6) . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C17 C8 1.356(6) . ? C17 C12 1.411(6) . ? C17 H17A 0.9300 . ? C16 C13 1.386(6) . ? C16 C15 1.387(6) . ? C16 H16A 0.9300 . ? C15 C2 1.497(6) . ? C14 C9 1.395(6) . ? C14 C4 1.506(6) . ? C13 C11 1.368(6) . ? C12 H12A 0.9300 . ? C11 H11A 0.9300 . ? C10 C7 1.397(6) . ? C10 H10A 0.9300 . ? C9 C6 1.375(7) . ? C9 H9A 0.9300 . ? C7 H7A 0.9300 . ? C6 C3 1.371(7) . ? C5 C3 1.362(7) . ? C5 H5A 0.9300 . ? C4 H4A 0.9600 . ? C4 H4B 0.9600 . ? C4 H4C 0.9600 . ? C3 H3A 0.9300 . ? C2 H2A 0.9600 . ? C2 H2B 0.9600 . ? C2 H2C 0.9600 . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? 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 C26 C28 C24 113.4(4) . . ? C26 C28 C25 124.7(4) . . ? C24 C28 C25 121.8(4) . . ? C21 C27 C8 124.4(4) . . ? C21 C27 C26 146.1(4) . . ? C8 C27 C26 89.5(4) . . ? C28 C26 C19 124.2(4) . . ? C28 C26 C27 145.4(4) . . ? C19 C26 C27 90.3(4) . . ? C20 C25 C15 118.7(4) . . ? C20 C25 C28 119.6(4) . . ? C15 C25 C28 121.7(4) . . ? C10 C24 C28 122.3(4) . . ? C10 C24 H24A 118.9 . . ? C28 C24 H24A 118.9 . . ? C12 C23 C21 123.0(5) . . ? C12 C23 H23A 118.5 . . ? C21 C23 H23A 118.5 . . ? C11 C20 C25 119.7(4) . . ? C11 C20 C1 119.4(4) . . ? C25 C20 C1 120.9(4) . . ? C14 C22 C5 119.2(5) . . ? C14 C22 C21 122.1(4) . . ? C5 C22 C21 118.8(4) . . ? C27 C21 C23 113.1(4) . . ? C27 C21 C22 125.2(4) . . ? C23 C21 C22 121.7(4) . . ? C7 C19 C26 121.9(4) . . ? C7 C19 C8 148.2(4) . . ? C26 C19 C8 89.9(4) . . ? C13 C18 H18A 109.5 . . ? C13 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C13 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C8 C17 C12 115.8(4) . . ? C8 C17 H17A 122.1 . . ? C12 C17 H17A 122.1 . . ? C13 C16 C15 122.7(4) . . ? C13 C16 H16A 118.7 . . ? C15 C16 H16A 118.7 . . ? C16 C15 C25 119.0(4) . . ? C16 C15 C2 119.6(4) . . ? C25 C15 C2 121.4(4) . . ? C22 C14 C9 119.2(5) . . ? C22 C14 C4 121.3(4) . . ? C9 C14 C4 119.4(5) . . ? C11 C13 C16 117.2(4) . . ? C11 C13 C18 122.9(4) . . ? C16 C13 C18 119.9(4) . . ? C23 C12 C17 122.4(5) . . ? C23 C12 H12A 118.8 . . ? C17 C12 H12A 118.8 . . ? C13 C11 C20 122.7(4) . . ? C13 C11 H11A 118.6 . . ? C20 C11 H11A 118.6 . . ? C24 C10 C7 122.5(4) . . ? C24 C10 H10A 118.7 . . ? C7 C10 H10A 118.7 . . ? C6 C9 C14 120.2(5) . . ? C6 C9 H9A 119.9 . . ? C14 C9 H9A 119.9 . . ? C17 C8 C27 121.2(4) . . ? C17 C8 C19 148.3(5) . . ? C27 C8 C19 90.4(4) . . ? C19 C7 C10 115.6(4) . . ? C19 C7 H7A 122.2 . . ? C10 C7 H7A 122.2 . . ? C3 C6 C9 120.4(5) . . ? C3 C6 Cl1 119.7(5) . . ? C9 C6 Cl1 119.9(5) . . ? C3 C5 C22 120.9(5) . . ? C3 C5 H5A 119.5 . . ? C22 C5 H5A 119.5 . . ? C14 C4 H4A 109.5 . . ? C14 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? C14 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? C5 C3 C6 120.0(5) . . ? C5 C3 H3A 120.0 . . ? C6 C3 H3A 120.0 . . ? C15 C2 H2A 109.5 . . ? C15 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? C15 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? C20 C1 H1A 109.5 . . ? C20 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C20 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C24 C28 C26 C19 2.0(6) . . . . ? C25 C28 C26 C19 -176.3(4) . . . . ? C24 C28 C26 C27 177.5(5) . . . . ? C25 C28 C26 C27 -0.8(9) . . . . ? C21 C27 C26 C28 2.5(11) . . . . ? C8 C27 C26 C28 -176.1(6) . . . . ? C21 C27 C26 C19 178.8(6) . . . . ? C8 C27 C26 C19 0.2(3) . . . . ? C26 C28 C25 C20 62.2(6) . . . . ? C24 C28 C25 C20 -116.0(5) . . . . ? C26 C28 C25 C15 -117.2(5) . . . . ? C24 C28 C25 C15 64.7(6) . . . . ? C26 C28 C24 C10 -0.7(6) . . . . ? C25 C28 C24 C10 177.6(4) . . . . ? C15 C25 C20 C11 1.4(6) . . . . ? C28 C25 C20 C11 -178.0(4) . . . . ? C15 C25 C20 C1 -176.7(4) . . . . ? C28 C25 C20 C1 4.0(6) . . . . ? C8 C27 C21 C23 2.7(6) . . . . ? C26 C27 C21 C23 -175.6(5) . . . . ? C8 C27 C21 C22 -177.4(4) . . . . ? C26 C27 C21 C22 4.3(9) . . . . ? C12 C23 C21 C27 -1.6(6) . . . . ? C12 C23 C21 C22 178.5(4) . . . . ? C14 C22 C21 C27 59.3(6) . . . . ? C5 C22 C21 C27 -120.4(5) . . . . ? C14 C22 C21 C23 -120.8(5) . . . . ? C5 C22 C21 C23 59.5(6) . . . . ? C28 C26 C19 C7 -2.1(7) . . . . ? C27 C26 C19 C7 -179.6(4) . . . . ? C28 C26 C19 C8 177.3(4) . . . . ? C27 C26 C19 C8 -0.1(3) . . . . ? C13 C16 C15 C25 2.2(6) . . . . ? C13 C16 C15 C2 -179.0(4) . . . . ? C20 C25 C15 C16 -2.7(6) . . . . ? C28 C25 C15 C16 176.6(4) . . . . ? C20 C25 C15 C2 178.5(4) . . . . ? C28 C25 C15 C2 -2.1(6) . . . . ? C5 C22 C14 C9 0.8(6) . . . . ? C21 C22 C14 C9 -178.9(4) . . . . ? C5 C22 C14 C4 -177.4(4) . . . . ? C21 C22 C14 C4 2.9(6) . . . . ? C15 C16 C13 C11 -0.2(6) . . . . ? C15 C16 C13 C18 179.8(4) . . . . ? C21 C23 C12 C17 -0.6(7) . . . . ? C8 C17 C12 C23 1.8(7) . . . . ? C16 C13 C11 C20 -1.3(6) . . . . ? C18 C13 C11 C20 178.7(4) . . . . ? C25 C20 C11 C13 0.7(6) . . . . ? C1 C20 C11 C13 178.8(4) . . . . ? C28 C24 C10 C7 -0.5(7) . . . . ? C22 C14 C9 C6 0.8(7) . . . . ? C4 C14 C9 C6 179.0(4) . . . . ? C12 C17 C8 C27 -0.7(6) . . . . ? C12 C17 C8 C19 174.6(6) . . . . ? C21 C27 C8 C17 -1.6(7) . . . . ? C26 C27 C8 C17 177.4(4) . . . . ? C21 C27 C8 C19 -179.2(4) . . . . ? C26 C27 C8 C19 -0.1(3) . . . . ? C7 C19 C8 C17 3.2(13) . . . . ? C26 C19 C8 C17 -175.9(7) . . . . ? C7 C19 C8 C27 179.2(7) . . . . ? C26 C19 C8 C27 0.2(3) . . . . ? C26 C19 C7 C10 0.7(6) . . . . ? C8 C19 C7 C10 -178.2(6) . . . . ? C24 C10 C7 C19 0.5(7) . . . . ? C14 C9 C6 C3 -1.7(7) . . . . ? C14 C9 C6 Cl1 178.4(3) . . . . ? C14 C22 C5 C3 -1.6(7) . . . . ? C21 C22 C5 C3 178.1(5) . . . . ? C22 C5 C3 C6 0.7(8) . . . . ? C9 C6 C3 C5 0.9(8) . . . . ? Cl1 C6 C3 C5 -179.2(4) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 22.51 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.336 _refine_diff_density_min -0.362 _refine_diff_density_rms 0.043 # Attachment '3d_CN.CIF' data_gahj3 _database_code_depnum_ccdc_archive 'CCDC 679272' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C29 H23 N' _chemical_formula_weight 385.48 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/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 8.3064(13) _cell_length_b 32.077(4) _cell_length_c 8.3998(16) _cell_angle_alpha 90.00 _cell_angle_beta 108.092(11) _cell_angle_gamma 90.00 _cell_volume 2127.4(6) _cell_formula_units_Z 4 _cell_measurement_temperature 297(2) _cell_measurement_reflns_used 60 _cell_measurement_theta_min 5.10 _cell_measurement_theta_max 11.56 _exptl_crystal_description Plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.204 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 816 _exptl_absorpt_coefficient_mu 0.069 _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 297(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker P4' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 97 _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5367 _diffrn_reflns_av_R_equivalents 0.0385 _diffrn_reflns_av_sigmaI/netI 0.0542 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 3 _diffrn_reflns_limit_k_min -38 _diffrn_reflns_limit_k_max 1 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 2.54 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3736 _reflns_number_gt 2082 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker SHELXTL' _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^)+(0.0684P)^2^+0.3990P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3736 _refine_ls_number_parameters 275 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1136 _refine_ls_R_factor_gt 0.0579 _refine_ls_wR_factor_ref 0.1626 _refine_ls_wR_factor_gt 0.1364 _refine_ls_goodness_of_fit_ref 1.017 _refine_ls_restrained_S_all 1.017 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.7266(3) 0.10241(7) 0.5350(3) 0.0486(6) Uani 1 1 d . . . C2 C 0.7969(3) 0.16445(7) 0.1678(3) 0.0505(7) Uani 1 1 d . . . C3 C 0.9159(3) 0.06727(7) 0.3944(3) 0.0472(6) Uani 1 1 d . . . C4 C 0.7035(3) 0.14903(7) 0.5090(3) 0.0499(6) Uani 1 1 d . . . C5 C 0.8500(3) 0.18460(7) 0.3229(3) 0.0523(7) Uani 1 1 d . . . C6 C 0.5986(3) 0.14972(7) 0.6131(3) 0.0517(7) Uani 1 1 d . . . C7 C 0.8987(3) 0.16684(7) 0.0665(3) 0.0555(7) Uani 1 1 d . . . H7A H 0.8643 0.1537 -0.0374 0.067 Uiso 1 1 calc R . . C8 C 0.6210(3) 0.10294(7) 0.6377(3) 0.0513(6) Uani 1 1 d . . . C9 C 0.8037(3) 0.06729(7) 0.5018(3) 0.0505(6) Uani 1 1 d . . . C10 C 0.7437(3) 0.18405(7) 0.4363(3) 0.0524(7) Uani 1 1 d . . . C11 C 0.7655(3) 0.03084(7) 0.5787(3) 0.0595(7) Uani 1 1 d . . . H11A H 0.8138 0.0057 0.5624 0.071 Uiso 1 1 calc R . . C12 C 1.1692(4) 0.09062(8) 0.3404(4) 0.0591(7) Uani 1 1 d . . . H12A H 1.2721 0.1047 0.3752 0.071 Uiso 1 1 calc R . . C13 C 0.9696(4) 0.05015(8) 0.1390(3) 0.0611(7) Uani 1 1 d . . . H13A H 0.9360 0.0371 0.0350 0.073 Uiso 1 1 calc R . . C14 C 1.0017(4) 0.20607(8) 0.3693(4) 0.0703(8) Uani 1 1 d . . . H14A H 1.0367 0.2195 0.4726 0.084 Uiso 1 1 calc R . . C15 C 1.1194(4) 0.07187(8) 0.1861(4) 0.0592(7) Uani 1 1 d . . . C16 C 0.6750(4) 0.22136(8) 0.4782(3) 0.0622(8) Uani 1 1 d . . . H16A H 0.7005 0.2465 0.4361 0.075 Uiso 1 1 calc R . . C17 C 1.0700(3) 0.08907(7) 0.4459(3) 0.0526(7) Uani 1 1 d . . . C18 C 0.8669(3) 0.04694(7) 0.2399(3) 0.0533(7) Uani 1 1 d . . . C19 C 0.5301(4) 0.18560(8) 0.6497(3) 0.0621(8) Uani 1 1 d . . . H19A H 0.4601 0.1860 0.7171 0.074 Uiso 1 1 calc R . . C20 C 1.0505(4) 0.18822(8) 0.1147(4) 0.0604(7) Uani 1 1 d . . . C21 C 0.5725(4) 0.22196(8) 0.5786(4) 0.0672(8) Uani 1 1 d . . . H21A H 0.5294 0.2474 0.6002 0.081 Uiso 1 1 calc R . . C22 C 0.6608(4) 0.03120(8) 0.6754(4) 0.0654(8) Uani 1 1 d . . . H22A H 0.6385 0.0062 0.7205 0.078 Uiso 1 1 calc R . . C23 C 1.1025(4) 0.20820(9) 0.2670(4) 0.0725(8) Uani 1 1 d . . . H23A H 1.2040 0.2229 0.3002 0.087 Uiso 1 1 calc R . . C24 C 0.5854(3) 0.06773(8) 0.7098(3) 0.0610(7) Uani 1 1 d . . . H24A H 0.5155 0.0678 0.7775 0.073 Uiso 1 1 calc R . . C25 C 0.6307(3) 0.14177(9) 0.1079(3) 0.0667(8) Uani 1 1 d . . . H25A H 0.5404 0.1605 0.1070 0.100 Uiso 1 1 calc R . . H25B H 0.6314 0.1189 0.1818 0.100 Uiso 1 1 calc R . . H25C H 0.6141 0.1314 -0.0032 0.100 Uiso 1 1 calc R . . C26 C 1.1532(4) 0.19058(9) 0.0054(4) 0.0709(8) Uani 1 1 d . . . C27 C 1.1309(4) 0.11046(10) 0.6139(3) 0.0760(9) Uani 1 1 d . . . H27A H 1.1331 0.0908 0.7007 0.114 Uiso 1 1 calc R . . H27B H 1.0554 0.1329 0.6167 0.114 Uiso 1 1 calc R . . H27C H 1.2428 0.1213 0.6311 0.114 Uiso 1 1 calc R . . C28 C 0.7032(4) 0.02287(9) 0.1803(4) 0.0771(9) Uani 1 1 d . . . H28A H 0.6143 0.0387 0.2021 0.116 Uiso 1 1 calc R . . H28B H 0.7159 -0.0033 0.2386 0.116 Uiso 1 1 calc R . . H28C H 0.6753 0.0178 0.0621 0.116 Uiso 1 1 calc R . . N29 N 1.2354(4) 0.19276(9) -0.0804(4) 0.0960(9) Uani 1 1 d . . . C30 C 1.2273(4) 0.07584(10) 0.0702(4) 0.0843(10) Uani 1 1 d . . . H30A H 1.3449 0.0753 0.1352 0.126 Uiso 1 1 calc R . . H30B H 1.2018 0.1017 0.0099 0.126 Uiso 1 1 calc R . . H30C H 1.2032 0.0530 -0.0076 0.126 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 C1 0.0560(15) 0.0372(13) 0.0535(15) 0.0024(11) 0.0180(13) -0.0014(12) C2 0.0593(17) 0.0376(13) 0.0533(16) 0.0043(12) 0.0155(14) 0.0033(12) C3 0.0511(16) 0.0338(12) 0.0567(16) 0.0043(11) 0.0168(13) 0.0065(11) C4 0.0605(17) 0.0387(14) 0.0528(15) -0.0023(11) 0.0208(14) 0.0015(12) C5 0.0700(18) 0.0314(12) 0.0557(16) 0.0027(11) 0.0195(14) -0.0008(13) C6 0.0589(17) 0.0440(15) 0.0519(15) -0.0010(11) 0.0169(14) 0.0036(12) C7 0.0693(19) 0.0424(14) 0.0536(16) 0.0031(12) 0.0173(15) 0.0054(14) C8 0.0555(16) 0.0464(14) 0.0527(15) 0.0025(12) 0.0178(13) -0.0003(12) C9 0.0561(16) 0.0394(14) 0.0549(15) 0.0023(11) 0.0158(13) 0.0002(12) C10 0.0678(18) 0.0398(14) 0.0498(14) -0.0029(11) 0.0186(14) -0.0007(13) C11 0.0703(19) 0.0385(14) 0.0702(18) 0.0055(12) 0.0228(16) 0.0052(13) C12 0.0551(17) 0.0495(15) 0.0727(19) 0.0097(14) 0.0197(16) 0.0023(13) C13 0.077(2) 0.0464(15) 0.0601(17) -0.0029(13) 0.0223(16) 0.0120(15) C14 0.088(2) 0.0571(17) 0.0686(19) -0.0126(14) 0.0277(18) -0.0210(16) C15 0.069(2) 0.0457(15) 0.0687(18) 0.0131(14) 0.0303(16) 0.0146(14) C16 0.087(2) 0.0389(14) 0.0623(17) -0.0002(12) 0.0253(17) 0.0006(14) C17 0.0547(16) 0.0459(14) 0.0547(16) 0.0047(12) 0.0134(14) 0.0062(13) C18 0.0594(17) 0.0366(13) 0.0633(17) -0.0045(12) 0.0183(15) 0.0058(12) C19 0.0696(19) 0.0571(17) 0.0628(17) -0.0050(13) 0.0254(15) 0.0078(15) C20 0.074(2) 0.0402(14) 0.0718(19) 0.0072(14) 0.0293(17) 0.0036(14) C21 0.091(2) 0.0402(15) 0.0704(18) -0.0053(13) 0.0258(17) 0.0125(15) C22 0.079(2) 0.0462(16) 0.0757(19) 0.0130(14) 0.0313(17) -0.0020(15) C23 0.076(2) 0.0581(18) 0.089(2) -0.0039(16) 0.0341(19) -0.0216(15) C24 0.0660(18) 0.0576(17) 0.0666(17) 0.0097(14) 0.0311(15) 0.0011(14) C25 0.0647(19) 0.0683(17) 0.0638(18) -0.0071(14) 0.0152(15) -0.0042(15) C26 0.083(2) 0.0518(17) 0.087(2) 0.0111(15) 0.040(2) 0.0061(16) C27 0.069(2) 0.084(2) 0.0678(19) -0.0064(16) 0.0111(16) -0.0104(17) C28 0.081(2) 0.0625(18) 0.085(2) -0.0195(16) 0.0220(18) -0.0131(16) N29 0.108(2) 0.0796(19) 0.119(3) 0.0099(17) 0.063(2) 0.0065(17) C30 0.101(2) 0.071(2) 0.099(2) 0.0130(18) 0.057(2) 0.0171(18) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C9 1.367(3) . ? C1 C8 1.409(3) . ? C1 C4 1.515(3) . ? C2 C7 1.375(3) . ? C2 C5 1.398(3) . ? C2 C25 1.502(4) . ? C3 C18 1.395(3) . ? C3 C17 1.404(3) . ? C3 C9 1.484(3) . ? C4 C10 1.369(3) . ? C4 C6 1.413(3) . ? C5 C14 1.382(4) . ? C5 C10 1.486(4) . ? C6 C19 1.360(3) . ? C6 C8 1.518(3) . ? C7 C20 1.381(4) . ? C7 H7A 0.9300 . ? C8 C24 1.357(3) . ? C9 C11 1.419(3) . ? C10 C16 1.417(3) . ? C11 C22 1.362(4) . ? C11 H11A 0.9300 . ? C12 C15 1.371(4) . ? C12 C17 1.385(3) . ? C12 H12A 0.9300 . ? C13 C15 1.373(4) . ? C13 C18 1.381(4) . ? C13 H13A 0.9300 . ? C14 C23 1.375(4) . ? C14 H14A 0.9300 . ? C15 C30 1.519(4) . ? C16 C21 1.372(4) . ? C16 H16A 0.9300 . ? C17 C27 1.508(4) . ? C18 C28 1.507(4) . ? C19 C21 1.404(4) . ? C19 H19A 0.9300 . ? C20 C23 1.375(4) . ? C20 C26 1.436(4) . ? C21 H21A 0.9300 . ? C22 C24 1.400(4) . ? C22 H22A 0.9300 . ? C23 H23A 0.9300 . ? C24 H24A 0.9300 . ? C25 H25A 0.9600 . ? C25 H25B 0.9600 . ? C25 H25C 0.9600 . ? C26 N29 1.138(4) . ? C27 H27A 0.9600 . ? C27 H27B 0.9600 . ? C27 H27C 0.9600 . ? C28 H28A 0.9600 . ? C28 H28B 0.9600 . ? C28 H28C 0.9600 . ? C30 H30A 0.9600 . ? C30 H30B 0.9600 . ? C30 H30C 0.9600 . ? 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 C9 C1 C8 123.7(2) . . ? C9 C1 C4 146.2(2) . . ? C8 C1 C4 90.06(19) . . ? C7 C2 C5 118.3(2) . . ? C7 C2 C25 119.8(2) . . ? C5 C2 C25 121.8(2) . . ? C18 C3 C17 119.6(2) . . ? C18 C3 C9 120.5(2) . . ? C17 C3 C9 119.8(2) . . ? C10 C4 C6 123.1(2) . . ? C10 C4 C1 146.8(2) . . ? C6 C4 C1 90.08(19) . . ? C14 C5 C2 119.3(3) . . ? C14 C5 C10 119.8(2) . . ? C2 C5 C10 120.9(2) . . ? C19 C6 C4 122.3(2) . . ? C19 C6 C8 147.9(3) . . ? C4 C6 C8 89.76(19) . . ? C2 C7 C20 121.8(3) . . ? C2 C7 H7A 119.1 . . ? C20 C7 H7A 119.1 . . ? C24 C8 C1 121.8(2) . . ? C24 C8 C6 148.1(3) . . ? C1 C8 C6 90.09(19) . . ? C1 C9 C11 113.6(2) . . ? C1 C9 C3 123.1(2) . . ? C11 C9 C3 123.2(2) . . ? C4 C10 C16 114.2(2) . . ? C4 C10 C5 124.9(2) . . ? C16 C10 C5 121.0(2) . . ? C22 C11 C9 122.6(2) . . ? C22 C11 H11A 118.7 . . ? C9 C11 H11A 118.7 . . ? C15 C12 C17 121.6(3) . . ? C15 C12 H12A 119.2 . . ? C17 C12 H12A 119.2 . . ? C15 C13 C18 122.6(3) . . ? C15 C13 H13A 118.7 . . ? C18 C13 H13A 118.7 . . ? C23 C14 C5 121.8(3) . . ? C23 C14 H14A 119.1 . . ? C5 C14 H14A 119.1 . . ? C12 C15 C13 118.4(3) . . ? C12 C15 C30 120.3(3) . . ? C13 C15 C30 121.3(3) . . ? C21 C16 C10 122.6(2) . . ? C21 C16 H16A 118.7 . . ? C10 C16 H16A 118.7 . . ? C12 C17 C3 119.2(2) . . ? C12 C17 C27 119.3(3) . . ? C3 C17 C27 121.6(2) . . ? C13 C18 C3 118.6(2) . . ? C13 C18 C28 120.0(3) . . ? C3 C18 C28 121.4(3) . . ? C6 C19 C21 115.4(3) . . ? C6 C19 H19A 122.3 . . ? C21 C19 H19A 122.3 . . ? C23 C20 C7 119.9(3) . . ? C23 C20 C26 119.6(3) . . ? C7 C20 C26 120.5(3) . . ? C16 C21 C19 122.3(2) . . ? C16 C21 H21A 118.8 . . ? C19 C21 H21A 118.8 . . ? C11 C22 C24 122.7(2) . . ? C11 C22 H22A 118.7 . . ? C24 C22 H22A 118.7 . . ? C14 C23 C20 118.9(3) . . ? C14 C23 H23A 120.6 . . ? C20 C23 H23A 120.6 . . ? C8 C24 C22 115.5(2) . . ? C8 C24 H24A 122.2 . . ? C22 C24 H24A 122.2 . . ? C2 C25 H25A 109.5 . . ? C2 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C2 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? N29 C26 C20 179.3(4) . . ? C17 C27 H27A 109.5 . . ? C17 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C17 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? C18 C28 H28A 109.5 . . ? C18 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C18 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? C15 C30 H30A 109.5 . . ? C15 C30 H30B 109.5 . . ? H30A C30 H30B 109.5 . . ? C15 C30 H30C 109.5 . . ? H30A C30 H30C 109.5 . . ? H30B C30 H30C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C9 C1 C4 C10 1.0(7) . . . . ? C8 C1 C4 C10 178.9(4) . . . . ? C9 C1 C4 C6 -177.5(4) . . . . ? C8 C1 C4 C6 0.4(2) . . . . ? C7 C2 C5 C14 -0.1(4) . . . . ? C25 C2 C5 C14 -178.0(2) . . . . ? C7 C2 C5 C10 178.5(2) . . . . ? C25 C2 C5 C10 0.5(4) . . . . ? C10 C4 C6 C19 -0.4(4) . . . . ? C1 C4 C6 C19 178.6(2) . . . . ? C10 C4 C6 C8 -179.4(2) . . . . ? C1 C4 C6 C8 -0.38(19) . . . . ? C5 C2 C7 C20 0.4(4) . . . . ? C25 C2 C7 C20 178.4(2) . . . . ? C9 C1 C8 C24 -1.3(4) . . . . ? C4 C1 C8 C24 -179.9(2) . . . . ? C9 C1 C8 C6 178.2(2) . . . . ? C4 C1 C8 C6 -0.38(19) . . . . ? C19 C6 C8 C24 1.2(8) . . . . ? C4 C6 C8 C24 179.6(4) . . . . ? C19 C6 C8 C1 -177.9(4) . . . . ? C4 C6 C8 C1 0.4(2) . . . . ? C8 C1 C9 C11 1.0(4) . . . . ? C4 C1 C9 C11 178.4(3) . . . . ? C8 C1 C9 C3 -179.4(2) . . . . ? C4 C1 C9 C3 -2.0(5) . . . . ? C18 C3 C9 C1 -112.6(3) . . . . ? C17 C3 C9 C1 65.2(3) . . . . ? C18 C3 C9 C11 67.0(3) . . . . ? C17 C3 C9 C11 -115.3(3) . . . . ? C6 C4 C10 C16 1.8(4) . . . . ? C1 C4 C10 C16 -176.4(4) . . . . ? C6 C4 C10 C5 -178.4(2) . . . . ? C1 C4 C10 C5 3.4(6) . . . . ? C14 C5 C10 C4 -117.3(3) . . . . ? C2 C5 C10 C4 64.1(4) . . . . ? C14 C5 C10 C16 62.4(3) . . . . ? C2 C5 C10 C16 -116.1(3) . . . . ? C1 C9 C11 C22 0.3(4) . . . . ? C3 C9 C11 C22 -179.2(2) . . . . ? C2 C5 C14 C23 0.0(4) . . . . ? C10 C5 C14 C23 -178.6(3) . . . . ? C17 C12 C15 C13 -1.9(4) . . . . ? C17 C12 C15 C30 177.2(2) . . . . ? C18 C13 C15 C12 0.8(4) . . . . ? C18 C13 C15 C30 -178.3(2) . . . . ? C4 C10 C16 C21 -2.1(4) . . . . ? C5 C10 C16 C21 178.1(3) . . . . ? C15 C12 C17 C3 0.9(4) . . . . ? C15 C12 C17 C27 -179.7(2) . . . . ? C18 C3 C17 C12 1.2(3) . . . . ? C9 C3 C17 C12 -176.6(2) . . . . ? C18 C3 C17 C27 -178.2(2) . . . . ? C9 C3 C17 C27 4.0(4) . . . . ? C15 C13 C18 C3 1.3(4) . . . . ? C15 C13 C18 C28 179.6(2) . . . . ? C17 C3 C18 C13 -2.2(3) . . . . ? C9 C3 C18 C13 175.6(2) . . . . ? C17 C3 C18 C28 179.5(2) . . . . ? C9 C3 C18 C28 -2.7(4) . . . . ? C4 C6 C19 C21 -0.7(4) . . . . ? C8 C6 C19 C21 177.3(4) . . . . ? C2 C7 C20 C23 -0.7(4) . . . . ? C2 C7 C20 C26 -179.3(2) . . . . ? C10 C16 C21 C19 1.1(4) . . . . ? C6 C19 C21 C16 0.4(4) . . . . ? C9 C11 C22 C24 -1.4(4) . . . . ? C5 C14 C23 C20 -0.2(4) . . . . ? C7 C20 C23 C14 0.6(4) . . . . ? C26 C20 C23 C14 179.2(3) . . . . ? C1 C8 C24 C22 0.2(4) . . . . ? C6 C8 C24 C22 -178.8(4) . . . . ? C11 C22 C24 C8 1.1(4) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.182 _refine_diff_density_min -0.174 _refine_diff_density_rms 0.036