# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full CrystEngComm _journal_coden_cambridge 1350 loop_ _publ_author_name _publ_author_address C.Cardellicchio ; CNR - ICCOM, Dipartimento di Chimica Universit\`a di Bari v. E. Orabona 4 - 70125 Bari Italy ; M.A.M.Capozzi ; Dipartimento di Scienze Agroambientali, Chimica e Difesa Vegetale Universit\`a di Foggia Via Napoli 25, 71100 Foggia Italy ; A.Alvarez-Larena ; Department of Geology Universitat Autonoma de Barcelona Campus Universitari UAB, 08193 Bellaterra Spain ; J.F.Piniella ; Department of Geology Universitat Autonoma de Barcelona Campus Universitari UAB, 08193 Bellaterra Spain ; ; F.Capitelli ; ; CNR - IC v. Salaria Km 29.300, 00016 Monterotondo (Roma) Italy ; _publ_contact_author_address ; CNR - Institute of Crystallography (IC) v. Salaria Km 29.300 - 00016 Monterotondo (Rome) Italy ; _publ_contact_author_email francesco.capitelli@ic.cnr.it _publ_contact_author_fax '+39 06 90672616' _publ_contact_author_phone '+39 06 90672630' #TrackingRef '- f1.cif' _publ_contact_author_name 'Dr. Francesco Capitelli' _publ_requested_category FO _publ_section_title ; Investigation on the Weak Interactions Assembling the Crystal Structures of Betti Bases ; # Attachment '- g15.cif' data_g15 _database_code_depnum_ccdc_archive 'CCDC 822815' #TrackingRef '- g15.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C25 H22 F N O' _chemical_formula_sum 'C25 H22 F N O' _chemical_formula_weight 371.44 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' O O 0.0106 0.0060 '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 orthorhombic _symmetry_space_group_name_H-M P212121 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' _cell_length_a 10.687(2) _cell_length_b 12.122(2) _cell_length_c 15.549(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2014.3(7) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 128 _cell_measurement_theta_min 3.21 _cell_measurement_theta_max 20.03 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.56 _exptl_crystal_size_mid 0.34 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.225 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 784 _exptl_absorpt_coefficient_mu 0.080 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9564 _exptl_absorpt_correction_T_max 0.9841 _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 'Nonius Kappa CCD' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14042 _diffrn_reflns_av_R_equivalents 0.0303 _diffrn_reflns_av_sigmaI/netI 0.0437 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.13 _diffrn_reflns_theta_max 29.18 _reflns_number_total 4931 _reflns_number_gt 3022 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius, 1998)' _computing_data_reduction 'EVALCCD (Duisenberg et al., 2003)' _computing_cell_refinement 'EVALCCD (Duisenberg et al., 2003)' _computing_structure_solution 'SIR97 (Altomare et al. 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'DIAMOND 2.1e (1998-2001 Crystal Impact GbR)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0335P)^2^+0.1268P] 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 0.3(11) _refine_ls_number_reflns 4931 _refine_ls_number_parameters 257 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0919 _refine_ls_R_factor_gt 0.0471 _refine_ls_wR_factor_ref 0.0976 _refine_ls_wR_factor_gt 0.0836 _refine_ls_goodness_of_fit_ref 1.006 _refine_ls_restrained_S_all 1.006 _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 F1 F 1.19013(13) 0.65520(14) 1.09940(9) 0.1111(5) Uani 1 1 d . . . O1 O 0.57453(15) 0.58387(13) 0.95436(10) 0.0761(4) Uani 1 1 d . . . H4 H 0.6320 0.5856 0.9195 0.114 Uiso 1 1 calc R . . N1 N 0.74863(16) 0.50141(14) 0.85961(10) 0.0529(4) Uani 1 1 d . . . H1N H 0.8132(19) 0.5263(16) 0.8317(12) 0.063 Uiso 1 1 d . . . C1 C 0.66214(18) 0.44474(16) 0.80007(11) 0.0539(5) Uani 1 1 d . . . H1 H 0.5888 0.4222 0.8336 0.065 Uiso 1 1 calc R . . C2 C 0.79144(16) 0.43720(14) 0.93493(10) 0.0433(4) Uani 1 1 d . . . H2 H 0.8205 0.3649 0.9151 0.052 Uiso 1 1 calc R . . C3 C 0.68433(17) 0.41999(15) 0.99861(11) 0.0456(4) Uani 1 1 d . . . C4 C 0.58652(18) 0.49345(17) 1.00496(13) 0.0577(5) Uani 1 1 d . . . C5 C 0.4912(2) 0.4790(2) 1.06693(18) 0.0774(7) Uani 1 1 d . . . H5 H 0.4238 0.5274 1.0683 0.093 Uiso 1 1 calc R . . C6 C 0.4972(2) 0.3959(3) 1.12369(17) 0.0868(8) Uani 1 1 d . . . H6 H 0.4332 0.3875 1.1637 0.104 Uiso 1 1 calc R . . C7 C 0.5981(2) 0.3210(2) 1.12426(14) 0.0700(6) Uani 1 1 d . . . C8 C 0.6093(3) 0.2374(3) 1.18717(17) 0.1009(10) Uani 1 1 d . . . H8 H 0.5488 0.2318 1.2299 0.121 Uiso 1 1 calc R . . C9 C 0.7052(4) 0.1661(3) 1.18660(19) 0.1102(11) Uani 1 1 d . . . H9 H 0.7120 0.1128 1.2294 0.132 Uiso 1 1 calc R . . C10 C 0.7940(3) 0.1722(2) 1.12202(17) 0.0912(8) Uani 1 1 d . . . H10 H 0.8590 0.1213 1.1208 0.109 Uiso 1 1 calc R . . C11 C 0.7877(2) 0.25177(17) 1.06007(14) 0.0655(5) Uani 1 1 d . . . H11 H 0.8488 0.2539 1.0175 0.079 Uiso 1 1 calc R . . C12 C 0.69060(18) 0.33101(16) 1.05887(11) 0.0526(5) Uani 1 1 d . . . C13 C 0.90016(17) 0.49649(15) 0.97771(10) 0.0443(4) Uani 1 1 d . . . C14 C 0.88685(19) 0.60405(16) 1.00676(12) 0.0554(5) Uani 1 1 d . . . H14 H 0.8114 0.6408 0.9986 0.066 Uiso 1 1 calc R . . C15 C 0.9846(2) 0.65739(19) 1.04775(13) 0.0670(6) Uani 1 1 d . . . H15 H 0.9757 0.7295 1.0672 0.080 Uiso 1 1 calc R . . C16 C 1.0941(2) 0.6019(2) 1.05893(13) 0.0705(6) Uani 1 1 d . . . C17 C 1.1107(2) 0.4972(2) 1.03221(14) 0.0721(6) Uani 1 1 d . . . H17 H 1.1864 0.4612 1.0414 0.086 Uiso 1 1 calc R . . C18 C 1.01345(18) 0.44430(17) 0.99096(13) 0.0580(5) Uani 1 1 d . . . H18 H 1.0243 0.3723 0.9717 0.070 Uiso 1 1 calc R . . C19 C 0.6179(2) 0.52990(19) 0.73459(14) 0.0810(7) Uani 1 1 d . . . H19A H 0.5861 0.5935 0.7642 0.122 Uiso 1 1 calc R . . H19B H 0.5530 0.4985 0.6997 0.122 Uiso 1 1 calc R . . H19C H 0.6869 0.5513 0.6987 0.122 Uiso 1 1 calc R . . C20 C 0.71342(17) 0.34231(16) 0.75714(11) 0.0517(5) Uani 1 1 d . . . C21 C 0.8056(2) 0.3487(2) 0.69565(12) 0.0684(6) Uani 1 1 d . . . H21 H 0.8410 0.4168 0.6828 0.082 Uiso 1 1 calc R . . C22 C 0.8463(2) 0.2563(3) 0.65269(14) 0.0816(7) Uani 1 1 d . . . H22 H 0.9088 0.2623 0.6113 0.098 Uiso 1 1 calc R . . C23 C 0.7953(3) 0.1556(2) 0.67073(16) 0.0889(8) Uani 1 1 d . . . H23 H 0.8214 0.0934 0.6406 0.107 Uiso 1 1 calc R . . C24 C 0.7058(3) 0.1462(2) 0.73296(18) 0.0904(8) Uani 1 1 d . . . H24 H 0.6725 0.0775 0.7465 0.108 Uiso 1 1 calc R . . C25 C 0.6654(2) 0.2390(2) 0.77548(14) 0.0719(6) Uani 1 1 d . . . H25 H 0.6042 0.2322 0.8177 0.086 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 F1 0.0874(10) 0.1380(13) 0.1080(10) -0.0164(10) -0.0256(9) -0.0484(9) O1 0.0754(11) 0.0660(10) 0.0870(12) -0.0083(9) -0.0013(8) 0.0235(8) N1 0.0572(10) 0.0550(10) 0.0465(9) 0.0010(8) -0.0018(7) -0.0078(8) C1 0.0523(11) 0.0638(13) 0.0457(10) -0.0040(10) -0.0043(9) -0.0021(10) C2 0.0475(10) 0.0420(10) 0.0405(9) -0.0047(8) 0.0006(8) 0.0009(8) C3 0.0444(10) 0.0470(10) 0.0452(10) -0.0097(9) 0.0020(8) -0.0044(8) C4 0.0510(12) 0.0601(13) 0.0620(12) -0.0171(12) 0.0003(10) 0.0020(10) C5 0.0485(13) 0.0928(19) 0.0909(17) -0.0343(17) 0.0140(12) -0.0029(12) C6 0.0692(17) 0.112(2) 0.0797(18) -0.0267(17) 0.0302(13) -0.0353(16) C7 0.0725(16) 0.0772(16) 0.0601(13) -0.0095(12) 0.0127(12) -0.0266(14) C8 0.134(3) 0.102(2) 0.0667(16) 0.0048(16) 0.0271(18) -0.051(2) C9 0.156(3) 0.097(2) 0.0771(19) 0.0257(18) -0.010(2) -0.032(2) C10 0.107(2) 0.0747(17) 0.0913(18) 0.0248(15) -0.0205(17) -0.0152(15) C11 0.0699(14) 0.0578(13) 0.0689(13) 0.0088(12) -0.0072(12) -0.0098(12) C12 0.0557(12) 0.0528(12) 0.0495(10) -0.0065(10) 0.0010(10) -0.0177(10) C13 0.0485(11) 0.0468(10) 0.0376(9) -0.0021(8) 0.0084(7) -0.0059(9) C14 0.0567(12) 0.0543(12) 0.0551(11) -0.0037(10) 0.0030(9) -0.0086(9) C15 0.0805(16) 0.0598(13) 0.0606(13) -0.0092(12) 0.0050(12) -0.0219(12) C16 0.0606(14) 0.0946(18) 0.0564(12) -0.0028(13) -0.0056(11) -0.0333(14) C17 0.0502(12) 0.0905(17) 0.0754(15) -0.0028(14) -0.0052(10) -0.0091(13) C18 0.0505(12) 0.0616(13) 0.0618(12) -0.0065(11) 0.0049(10) -0.0009(10) C19 0.0890(18) 0.0874(17) 0.0668(14) -0.0015(13) -0.0218(13) 0.0213(14) C20 0.0503(11) 0.0646(13) 0.0400(9) -0.0048(10) -0.0076(9) -0.0014(10) C21 0.0732(15) 0.0811(16) 0.0510(11) 0.0025(11) 0.0076(11) 0.0036(13) C22 0.0832(18) 0.110(2) 0.0513(12) -0.0070(15) 0.0097(12) 0.0170(17) C23 0.094(2) 0.093(2) 0.0795(17) -0.0313(16) -0.0141(16) 0.0228(18) C24 0.0920(19) 0.0644(16) 0.115(2) -0.0167(16) 0.0003(18) -0.0036(15) C25 0.0695(14) 0.0722(16) 0.0739(14) -0.0099(13) 0.0071(12) -0.0089(13) _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 F1 C16 1.366(2) . ? O1 C4 1.355(2) . ? N1 C1 1.478(2) . ? N1 C2 1.479(2) . ? C1 C20 1.512(3) . ? C1 C19 1.525(3) . ? C2 C13 1.520(2) . ? C2 C3 1.528(2) . ? C3 C4 1.377(3) . ? C3 C12 1.430(2) . ? C4 C5 1.413(3) . ? C5 C6 1.340(3) . ? C6 C7 1.410(4) . ? C7 C8 1.414(4) . ? C7 C12 1.423(3) . ? C8 C9 1.341(4) . ? C9 C10 1.383(4) . ? C10 C11 1.365(3) . ? C11 C12 1.414(3) . ? C13 C18 1.381(3) . ? C13 C14 1.387(2) . ? C14 C15 1.384(3) . ? C15 C16 1.361(3) . ? C16 C17 1.348(3) . ? C17 C18 1.379(3) . ? C20 C21 1.375(3) . ? C20 C25 1.383(3) . ? C21 C22 1.376(3) . ? C22 C23 1.366(4) . ? C23 C24 1.365(4) . ? C24 C25 1.375(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 C2 116.43(15) . . ? N1 C1 C20 115.56(15) . . ? N1 C1 C19 107.31(16) . . ? C20 C1 C19 111.93(15) . . ? N1 C2 C13 109.53(14) . . ? N1 C2 C3 110.69(14) . . ? C13 C2 C3 110.72(13) . . ? C4 C3 C12 118.45(17) . . ? C4 C3 C2 121.80(17) . . ? C12 C3 C2 119.50(15) . . ? O1 C4 C3 123.59(18) . . ? O1 C4 C5 115.3(2) . . ? C3 C4 C5 121.1(2) . . ? C6 C5 C4 120.5(2) . . ? C5 C6 C7 121.6(2) . . ? C6 C7 C8 122.1(3) . . ? C6 C7 C12 118.2(2) . . ? C8 C7 C12 119.8(3) . . ? C9 C8 C7 121.5(3) . . ? C8 C9 C10 119.6(3) . . ? C11 C10 C9 121.1(3) . . ? C10 C11 C12 121.7(2) . . ? C11 C12 C7 116.26(19) . . ? C11 C12 C3 123.73(17) . . ? C7 C12 C3 120.0(2) . . ? C18 C13 C14 118.15(18) . . ? C18 C13 C2 121.25(16) . . ? C14 C13 C2 120.57(17) . . ? C15 C14 C13 120.8(2) . . ? C16 C15 C14 118.5(2) . . ? C17 C16 C15 122.6(2) . . ? C17 C16 F1 119.3(2) . . ? C15 C16 F1 118.1(2) . . ? C16 C17 C18 118.8(2) . . ? C17 C18 C13 121.13(19) . . ? C21 C20 C25 117.4(2) . . ? C21 C20 C1 121.34(19) . . ? C25 C20 C1 121.19(17) . . ? C20 C21 C22 121.2(2) . . ? C23 C22 C21 120.1(2) . . ? C24 C23 C22 120.0(2) . . ? C23 C24 C25 119.6(3) . . ? C24 C25 C20 121.7(2) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1 H4 N1 0.82 1.86 2.575(2) 145.0 . C5 H5 F1 0.93 2.98 3.895(3) 169.1 1_455 C9 H9 F1 0.93 2.91 3.513(3) 124.0 3_747 C15 H15 O1 0.93 2.52 3.281(3) 139.3 4_567 _diffrn_measured_fraction_theta_max 0.938 _diffrn_reflns_theta_full 29.18 _diffrn_measured_fraction_theta_full 0.938 _refine_diff_density_max 0.122 _refine_diff_density_min -0.129 _refine_diff_density_rms 0.025 # Attachment '- f9.cif' data_f9 _database_code_depnum_ccdc_archive 'CCDC 822816' #TrackingRef '- f9.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C25 H22 Cl N O' _chemical_formula_sum 'C25 H22 Cl N O' _chemical_formula_weight 387.89 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' O O 0.0106 0.0060 '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 P212121 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 10.6982(8) _cell_length_b 12.1633(9) _cell_length_c 15.7632(12) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2051.2(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2160 _cell_measurement_theta_min 2.53 _cell_measurement_theta_max 20.71 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.23 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.256 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 816 _exptl_absorpt_coefficient_mu 0.201 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9458 _exptl_absorpt_correction_T_max 0.9552 _exptl_absorpt_process_details SADABS _exptl_special_details ; Sheldrick, G. M. SADABS, Absorption Correction Program. University of G ttingen, Germany, 1996. ; _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 SMART APEX' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14206 _diffrn_reflns_av_R_equivalents 0.0363 _diffrn_reflns_av_sigmaI/netI 0.0513 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.11 _diffrn_reflns_theta_max 29.03 _reflns_number_total 4998 _reflns_number_gt 3104 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART 5.6 (Bruker)' _computing_cell_refinement 'SAINT 5.0 (Bruker)' _computing_data_reduction 'SAINT 5.0 (Bruker)' _computing_structure_solution 'SIR97 (Altomare et al., 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'DIAMOND 2.1e (1998-2001 Crystal Impact GbR)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0388P)^2^+0.0352P] 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 0.02(7) _refine_ls_number_reflns 4998 _refine_ls_number_parameters 257 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0922 _refine_ls_R_factor_gt 0.0490 _refine_ls_wR_factor_ref 0.1020 _refine_ls_wR_factor_gt 0.0887 _refine_ls_goodness_of_fit_ref 1.015 _refine_ls_restrained_S_all 1.015 _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 Cl1 Cl 1.19479(7) 0.66879(6) 1.12232(5) 0.0841(3) Uani 1 1 d . . . O1 O 0.56724(16) 0.58456(14) 0.94707(12) 0.0741(5) Uani 1 1 d . . . H4 H 0.6247 0.5851 0.9126 0.111 Uiso 1 1 calc R . . N1 N 0.74553(18) 0.50291(15) 0.85678(11) 0.0498(4) Uani 1 1 d . . . H1N H 0.813(2) 0.5278(18) 0.8299(13) 0.060 Uiso 1 1 d . . . C1 C 0.6627(2) 0.44806(18) 0.79507(13) 0.0535(6) Uani 1 1 d . . . H1 H 0.5877 0.4246 0.8259 0.064 Uiso 1 1 calc R . . C2 C 0.7838(2) 0.43748(16) 0.93133(12) 0.0435(5) Uani 1 1 d . . . H2 H 0.8135 0.3655 0.9121 0.052 Uiso 1 1 calc R . . C3 C 0.6744(2) 0.42091(17) 0.99219(12) 0.0457(5) Uani 1 1 d . . . C4 C 0.5774(2) 0.4946(2) 0.99737(15) 0.0579(6) Uani 1 1 d . . . C5 C 0.4804(3) 0.4818(3) 1.0573(2) 0.0823(9) Uani 1 1 d . . . H5 H 0.4139 0.5311 1.0580 0.099 Uiso 1 1 calc R . . C6 C 0.4838(3) 0.3979(3) 1.1138(2) 0.0906(10) Uani 1 1 d . . . H6 H 0.4197 0.3905 1.1532 0.109 Uiso 1 1 calc R . . C7 C 0.5820(3) 0.3225(2) 1.11361(15) 0.0708(7) Uani 1 1 d . . . C8 C 0.5883(4) 0.2367(3) 1.17465(19) 0.1001(12) Uani 1 1 d . . . H8 H 0.5264 0.2319 1.2159 0.120 Uiso 1 1 calc R . . C9 C 0.6805(4) 0.1627(3) 1.1746(2) 0.1089(13) Uani 1 1 d . . . H9 H 0.6824 0.1075 1.2153 0.131 Uiso 1 1 calc R . . C10 C 0.7739(3) 0.1687(2) 1.11311(19) 0.0879(9) Uani 1 1 d . . . H10 H 0.8378 0.1168 1.1126 0.106 Uiso 1 1 calc R . . C11 C 0.7721(3) 0.2508(2) 1.05336(15) 0.0657(7) Uani 1 1 d . . . H11 H 0.8355 0.2536 1.0131 0.079 Uiso 1 1 calc R . . C12 C 0.6773(2) 0.33089(18) 1.05118(13) 0.0543(6) Uani 1 1 d . . . C13 C 0.88961(19) 0.49637(17) 0.97660(12) 0.0420(5) Uani 1 1 d . . . C14 C 0.8752(2) 0.60462(17) 1.00378(13) 0.0479(5) Uani 1 1 d . . . H14 H 0.8009 0.6415 0.9924 0.057 Uiso 1 1 calc R . . C15 C 0.9686(2) 0.65793(18) 1.04710(13) 0.0522(6) Uani 1 1 d . . . H15 H 0.9580 0.7304 1.0646 0.063 Uiso 1 1 calc R . . C16 C 1.0782(2) 0.60287(19) 1.06435(13) 0.0516(6) Uani 1 1 d . . . C17 C 1.0953(2) 0.49730(19) 1.03865(14) 0.0559(6) Uani 1 1 d . . . H17 H 1.1697 0.4610 1.0507 0.067 Uiso 1 1 calc R . . C18 C 1.0012(2) 0.44419(18) 0.99441(14) 0.0512(6) Uani 1 1 d . . . H18 H 1.0133 0.3722 0.9764 0.061 Uiso 1 1 calc R . . C19 C 0.6222(3) 0.5345(2) 0.73137(16) 0.0808(8) Uani 1 1 d . . . H19A H 0.5881 0.5966 0.7609 0.121 Uiso 1 1 calc R . . H19B H 0.5598 0.5041 0.6944 0.121 Uiso 1 1 calc R . . H19C H 0.6931 0.5574 0.6985 0.121 Uiso 1 1 calc R . . C20 C 0.7167(2) 0.34711(18) 0.75240(13) 0.0510(6) Uani 1 1 d . . . C21 C 0.8110(2) 0.3565(2) 0.69281(14) 0.0649(7) Uani 1 1 d . . . H21 H 0.8460 0.4251 0.6820 0.078 Uiso 1 1 calc R . . C22 C 0.8538(3) 0.2655(3) 0.64918(16) 0.0800(8) Uani 1 1 d . . . H22 H 0.9166 0.2735 0.6088 0.096 Uiso 1 1 calc R . . C23 C 0.8048(3) 0.1643(3) 0.66476(19) 0.0877(9) Uani 1 1 d . . . H23 H 0.8335 0.1034 0.6348 0.105 Uiso 1 1 calc R . . C24 C 0.7135(3) 0.1522(2) 0.72443(19) 0.0869(9) Uani 1 1 d . . . H24 H 0.6812 0.0829 0.7362 0.104 Uiso 1 1 calc R . . C25 C 0.6689(2) 0.2438(2) 0.76750(16) 0.0690(7) Uani 1 1 d . . . H25 H 0.6055 0.2352 0.8073 0.083 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 0.0730(5) 0.0818(5) 0.0976(5) -0.0120(4) -0.0310(4) -0.0145(4) O1 0.0675(13) 0.0615(11) 0.0933(14) -0.0097(10) 0.0004(10) 0.0182(9) N1 0.0532(11) 0.0542(11) 0.0421(9) 0.0009(8) -0.0067(9) -0.0074(9) C1 0.0484(14) 0.0630(15) 0.0491(12) -0.0084(11) -0.0090(11) -0.0022(12) C2 0.0469(13) 0.0432(11) 0.0405(11) -0.0062(9) 0.0011(10) 0.0011(10) C3 0.0448(13) 0.0467(12) 0.0457(11) -0.0070(10) 0.0001(11) -0.0073(11) C4 0.0515(14) 0.0573(16) 0.0648(15) -0.0190(13) 0.0028(13) -0.0035(13) C5 0.0504(16) 0.089(2) 0.107(2) -0.041(2) 0.0175(17) -0.0097(16) C6 0.075(2) 0.109(3) 0.088(2) -0.035(2) 0.0375(19) -0.040(2) C7 0.0805(19) 0.0778(19) 0.0542(14) -0.0172(15) 0.0113(15) -0.0358(16) C8 0.143(4) 0.103(3) 0.0546(17) -0.0076(19) 0.016(2) -0.067(3) C9 0.169(4) 0.096(3) 0.0619(19) 0.0164(19) -0.019(3) -0.051(3) C10 0.115(2) 0.0670(18) 0.0817(19) 0.0182(16) -0.037(2) -0.0195(18) C11 0.0764(19) 0.0605(14) 0.0602(14) 0.0033(13) -0.0106(14) -0.0125(15) C12 0.0628(15) 0.0540(13) 0.0462(12) -0.0118(11) 0.0003(12) -0.0195(13) C13 0.0443(12) 0.0468(12) 0.0349(10) -0.0006(9) 0.0043(9) -0.0017(10) C14 0.0446(13) 0.0447(12) 0.0544(12) -0.0036(10) -0.0011(11) 0.0013(10) C15 0.0603(15) 0.0445(12) 0.0519(13) -0.0019(11) -0.0012(12) -0.0073(12) C16 0.0490(14) 0.0583(14) 0.0476(12) 0.0020(11) -0.0015(11) -0.0107(12) C17 0.0447(13) 0.0611(15) 0.0619(14) -0.0036(12) -0.0014(11) 0.0032(12) C18 0.0471(14) 0.0499(13) 0.0567(14) -0.0094(11) 0.0045(12) 0.0038(11) C19 0.093(2) 0.0807(18) 0.0685(16) -0.0005(14) -0.0297(17) 0.0208(17) C20 0.0535(14) 0.0581(14) 0.0414(11) -0.0065(11) -0.0087(11) 0.0002(12) C21 0.0716(17) 0.0718(17) 0.0512(13) -0.0001(12) 0.0002(14) 0.0035(14) C22 0.094(2) 0.094(2) 0.0521(14) -0.0053(15) 0.0034(15) 0.0202(19) C23 0.103(2) 0.085(2) 0.0744(18) -0.0263(17) -0.0111(19) 0.023(2) C24 0.094(2) 0.0609(17) 0.106(2) -0.0120(17) -0.010(2) -0.0013(18) C25 0.0669(17) 0.0683(17) 0.0719(16) -0.0098(14) 0.0045(15) -0.0033(16) _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 C16 1.741(2) . ? O1 C4 1.355(3) . ? N1 C1 1.475(3) . ? N1 C2 1.477(2) . ? C1 C20 1.515(3) . ? C1 C19 1.517(3) . ? C2 C13 1.518(3) . ? C2 C3 1.526(3) . ? C3 C4 1.374(3) . ? C3 C12 1.437(3) . ? C4 C5 1.412(4) . ? C5 C6 1.354(4) . ? C6 C7 1.395(4) . ? C7 C12 1.420(3) . ? C7 C8 1.421(4) . ? C8 C9 1.335(5) . ? C9 C10 1.393(5) . ? C10 C11 1.373(3) . ? C11 C12 1.406(3) . ? C13 C18 1.381(3) . ? C13 C14 1.393(3) . ? C14 C15 1.373(3) . ? C15 C16 1.377(3) . ? C16 C17 1.359(3) . ? C17 C18 1.385(3) . ? C20 C25 1.377(3) . ? C20 C21 1.383(3) . ? C21 C22 1.382(4) . ? C22 C23 1.360(4) . ? C23 C24 1.364(4) . ? C24 C25 1.389(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 C2 116.57(17) . . ? N1 C1 C20 115.48(18) . . ? N1 C1 C19 107.14(18) . . ? C20 C1 C19 112.13(18) . . ? N1 C2 C13 109.04(16) . . ? N1 C2 C3 111.05(18) . . ? C13 C2 C3 109.79(15) . . ? C4 C3 C12 118.4(2) . . ? C4 C3 C2 122.0(2) . . ? C12 C3 C2 119.41(19) . . ? O1 C4 C3 123.5(2) . . ? O1 C4 C5 114.9(2) . . ? C3 C4 C5 121.5(3) . . ? C6 C5 C4 120.2(3) . . ? C5 C6 C7 121.0(3) . . ? C6 C7 C12 119.7(3) . . ? C6 C7 C8 121.1(3) . . ? C12 C7 C8 119.2(3) . . ? C9 C8 C7 121.9(3) . . ? C8 C9 C10 119.7(3) . . ? C11 C10 C9 120.3(3) . . ? C10 C11 C12 122.1(3) . . ? C11 C12 C7 116.8(2) . . ? C11 C12 C3 124.0(2) . . ? C7 C12 C3 119.2(2) . . ? C18 C13 C14 117.87(19) . . ? C18 C13 C2 121.57(18) . . ? C14 C13 C2 120.54(18) . . ? C15 C14 C13 121.3(2) . . ? C14 C15 C16 119.2(2) . . ? C17 C16 C15 121.0(2) . . ? C17 C16 Cl1 119.70(18) . . ? C15 C16 Cl1 119.29(18) . . ? C16 C17 C18 119.6(2) . . ? C13 C18 C17 121.1(2) . . ? C25 C20 C21 117.6(2) . . ? C25 C20 C1 121.4(2) . . ? C21 C20 C1 120.8(2) . . ? C22 C21 C20 120.9(3) . . ? C23 C22 C21 120.5(3) . . ? C22 C23 C24 119.8(3) . . ? C23 C24 C25 119.8(3) . . ? C20 C25 C24 121.3(3) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1 H4 N1 0.82 1.86 2.579(3) 146.3 . C9 H9 Cl1 0.93 2.97 3.469(3) 115.0 4_747 C15 H15 O1 0.93 2.54 3.306(3) 139.6 3_567 _diffrn_measured_fraction_theta_max 0.935 _diffrn_reflns_theta_full 29.03 _diffrn_measured_fraction_theta_full 0.935 _refine_diff_density_max 0.120 _refine_diff_density_min -0.193 _refine_diff_density_rms 0.028 # Attachment '- f13.cif' data_f13 _database_code_depnum_ccdc_archive 'CCDC 822817' #TrackingRef '- f13.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C25 H22 Br N O' _chemical_formula_sum 'C25 H22 Br N O' _chemical_formula_weight 432.35 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M P212121 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 10.6828(6) _cell_length_b 12.1716(7) _cell_length_c 15.9646(9) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2075.8(2) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 4533 _cell_measurement_theta_min 2.29 _cell_measurement_theta_max 22.52 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.58 _exptl_crystal_size_mid 0.52 _exptl_crystal_size_min 0.50 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.383 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 888 _exptl_absorpt_coefficient_mu 1.995 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.3908 _exptl_absorpt_correction_T_max 0.4353 _exptl_absorpt_process_details SADABS _exptl_special_details ; Sheldrick, G. M. SADABS, Absorption Correction Program. University of G ttingen, Germany, 1996. ; _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 SMART APEX' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14211 _diffrn_reflns_av_R_equivalents 0.0269 _diffrn_reflns_av_sigmaI/netI 0.0496 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.10 _diffrn_reflns_theta_max 29.02 _reflns_number_total 5019 _reflns_number_gt 3678 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART 5.6 (Bruker)' _computing_cell_refinement 'SAINT 5.0 (Bruker)' _computing_data_reduction 'SAINT 5.0 (Bruker)' _computing_structure_solution 'SIR97 (Altomare et al., 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'DIAMOND 2.1e (1998-2001 Crystal Impact GbR)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0339P)^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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.008(7) _refine_ls_number_reflns 5019 _refine_ls_number_parameters 257 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0552 _refine_ls_R_factor_gt 0.0356 _refine_ls_wR_factor_ref 0.0707 _refine_ls_wR_factor_gt 0.0666 _refine_ls_goodness_of_fit_ref 0.898 _refine_ls_restrained_S_all 0.898 _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 Br1 Br 1.19190(3) 0.66600(2) 1.138302(19) 0.06762(11) Uani 1 1 d . . . O1 O 0.56482(17) 0.58953(14) 0.93695(12) 0.0623(5) Uani 1 1 d . . . H4 H 0.6218 0.5865 0.9027 0.093 Uiso 1 1 calc R . . N1 N 0.74684(19) 0.50314(15) 0.85400(11) 0.0402(4) Uani 1 1 d . . . H1N H 0.815(2) 0.5311(19) 0.8350(14) 0.048 Uiso 1 1 d . . . C1 C 0.6673(2) 0.44899(19) 0.79035(14) 0.0463(6) Uani 1 1 d . . . H1 H 0.5905 0.4253 0.8187 0.056 Uiso 1 1 calc R . . C2 C 0.77955(18) 0.43725(17) 0.92919(13) 0.0360(5) Uani 1 1 d . . . H2 H 0.8088 0.3646 0.9115 0.043 Uiso 1 1 calc R . . C3 C 0.66624(19) 0.42383(18) 0.98644(13) 0.0376(5) Uani 1 1 d . . . C4 C 0.5701(2) 0.5007(2) 0.98782(15) 0.0490(6) Uani 1 1 d . . . C5 C 0.4695(2) 0.4911(3) 1.04395(19) 0.0669(8) Uani 1 1 d . . . H5 H 0.4039 0.5413 1.0414 0.080 Uiso 1 1 calc R . . C6 C 0.4671(3) 0.4107(3) 1.1011(2) 0.0703(9) Uani 1 1 d . . . H6 H 0.4006 0.4069 1.1386 0.084 Uiso 1 1 calc R . . C7 C 0.5633(2) 0.3316(3) 1.10566(15) 0.0592(7) Uani 1 1 d . . . C8 C 0.5635(4) 0.2479(3) 1.16642(16) 0.0769(10) Uani 1 1 d . . . H8 H 0.4985 0.2451 1.2051 0.092 Uiso 1 1 calc R . . C9 C 0.6539(4) 0.1722(3) 1.17035(18) 0.0855(11) Uani 1 1 d . . . H9 H 0.6516 0.1185 1.2117 0.103 Uiso 1 1 calc R . . C10 C 0.7526(3) 0.1736(3) 1.11215(18) 0.0725(9) Uani 1 1 d . . . H10 H 0.8150 0.1204 1.1146 0.087 Uiso 1 1 calc R . . C11 C 0.7564(2) 0.2539(2) 1.05148(16) 0.0540(6) Uani 1 1 d . . . H11 H 0.8219 0.2541 1.0131 0.065 Uiso 1 1 calc R . . C12 C 0.6632(2) 0.3362(2) 1.04617(13) 0.0440(5) Uani 1 1 d . . . C13 C 0.88442(19) 0.49574(17) 0.97632(12) 0.0339(5) Uani 1 1 d . . . C14 C 0.8715(2) 0.60381(18) 1.00260(13) 0.0386(5) Uani 1 1 d . . . H14 H 0.7991 0.6421 0.9885 0.046 Uiso 1 1 calc R . . C15 C 0.9620(2) 0.65590(19) 1.04867(13) 0.0410(5) Uani 1 1 d . . . H15 H 0.9513 0.7282 1.0662 0.049 Uiso 1 1 calc R . . C16 C 1.06924(19) 0.59856(19) 1.06846(13) 0.0400(5) Uani 1 1 d . . . C17 C 1.0871(2) 0.4924(2) 1.04335(14) 0.0442(5) Uani 1 1 d . . . H17 H 1.1602 0.4552 1.0572 0.053 Uiso 1 1 calc R . . C18 C 0.9943(2) 0.4414(2) 0.99694(14) 0.0417(6) Uani 1 1 d . . . H18 H 1.0059 0.3693 0.9793 0.050 Uiso 1 1 calc R . . C19 C 0.6303(3) 0.5394(2) 0.72808(17) 0.0697(8) Uani 1 1 d . . . H19A H 0.5959 0.6008 0.7581 0.105 Uiso 1 1 calc R . . H19B H 0.5688 0.5113 0.6898 0.105 Uiso 1 1 calc R . . H19C H 0.7029 0.5627 0.6974 0.105 Uiso 1 1 calc R . . C20 C 0.7222(2) 0.3491(2) 0.74787(13) 0.0451(6) Uani 1 1 d . . . C21 C 0.8167(2) 0.3589(2) 0.68940(15) 0.0561(6) Uani 1 1 d . . . H21 H 0.8508 0.4278 0.6785 0.067 Uiso 1 1 calc R . . C22 C 0.8612(3) 0.2691(3) 0.64709(17) 0.0710(8) Uani 1 1 d . . . H22 H 0.9254 0.2778 0.6083 0.085 Uiso 1 1 calc R . . C23 C 0.8128(4) 0.1676(3) 0.66121(19) 0.0816(9) Uani 1 1 d . . . H23 H 0.8428 0.1071 0.6317 0.098 Uiso 1 1 calc R . . C24 C 0.7188(3) 0.1548(3) 0.7196(2) 0.0814(10) Uani 1 1 d . . . H24 H 0.6851 0.0856 0.7298 0.098 Uiso 1 1 calc R . . C25 C 0.6748(3) 0.2453(2) 0.76292(17) 0.0613(7) Uani 1 1 d . . . H25 H 0.6124 0.2362 0.8029 0.074 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 Br1 0.06039(16) 0.06445(17) 0.0780(2) -0.01351(15) -0.02785(15) -0.00745(15) O1 0.0585(12) 0.0510(11) 0.0773(14) -0.0027(9) 0.0053(10) 0.0133(9) N1 0.0475(10) 0.0408(10) 0.0325(10) 0.0005(9) -0.0055(9) -0.0063(8) C1 0.0467(15) 0.0526(14) 0.0396(13) -0.0072(10) -0.0094(11) 0.0008(11) C2 0.0399(13) 0.0343(12) 0.0338(12) -0.0041(9) 0.0000(9) 0.0014(9) C3 0.0369(13) 0.0396(12) 0.0362(12) -0.0069(9) -0.0023(10) -0.0059(9) C4 0.0423(13) 0.0474(15) 0.0572(16) -0.0124(12) 0.0052(11) -0.0022(11) C5 0.0426(15) 0.072(2) 0.086(2) -0.0217(17) 0.0143(14) -0.0054(14) C6 0.0528(16) 0.089(2) 0.069(2) -0.0270(17) 0.0242(15) -0.0261(16) C7 0.0653(16) 0.0698(17) 0.0425(13) -0.0136(14) 0.0081(12) -0.0334(16) C8 0.093(3) 0.093(3) 0.0447(18) -0.0031(16) 0.0047(16) -0.046(2) C9 0.119(3) 0.093(2) 0.0450(17) 0.0231(17) -0.0219(18) -0.051(2) C10 0.0848(19) 0.0636(18) 0.069(2) 0.0175(16) -0.0310(17) -0.0202(16) C11 0.0605(15) 0.0502(15) 0.0513(16) 0.0037(12) -0.0113(12) -0.0156(13) C12 0.0459(13) 0.0485(13) 0.0376(12) -0.0115(11) -0.0035(9) -0.0149(11) C13 0.0369(11) 0.0399(12) 0.0249(11) -0.0008(9) 0.0032(9) -0.0014(9) C14 0.0358(11) 0.0398(13) 0.0402(13) 0.0011(10) -0.0028(10) 0.0020(9) C15 0.0494(12) 0.0334(12) 0.0401(12) -0.0020(10) -0.0007(10) -0.0030(11) C16 0.0372(13) 0.0484(14) 0.0344(13) -0.0018(10) -0.0032(10) -0.0094(10) C17 0.0342(12) 0.0522(15) 0.0462(14) -0.0037(11) 0.0000(10) 0.0044(10) C18 0.0406(13) 0.0413(14) 0.0431(14) -0.0089(10) 0.0052(10) 0.0029(9) C19 0.090(2) 0.0639(18) 0.0549(17) -0.0033(13) -0.0310(15) 0.0217(16) C20 0.0523(15) 0.0489(15) 0.0339(12) -0.0013(10) -0.0144(10) 0.0036(11) C21 0.0646(16) 0.0607(17) 0.0430(14) 0.0033(11) -0.0012(14) 0.0067(14) C22 0.090(2) 0.080(2) 0.0429(16) -0.0023(15) 0.0026(15) 0.0219(17) C23 0.109(3) 0.074(2) 0.0620(19) -0.0265(16) -0.0112(18) 0.032(2) C24 0.111(3) 0.0483(18) 0.085(2) -0.0159(15) -0.018(2) 0.0027(18) C25 0.0667(18) 0.0585(17) 0.0587(17) -0.0075(13) -0.0010(15) -0.0049(15) _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 Br1 C16 1.906(2) . ? O1 C4 1.354(3) . ? N1 C1 1.480(3) . ? N1 C2 1.485(3) . ? C1 C20 1.510(3) . ? C1 C19 1.535(3) . ? C2 C3 1.526(3) . ? C2 C13 1.526(3) . ? C3 C4 1.389(3) . ? C3 C12 1.431(3) . ? C4 C5 1.403(3) . ? C5 C6 1.338(4) . ? C6 C7 1.411(4) . ? C7 C8 1.407(4) . ? C7 C12 1.430(3) . ? C8 C9 1.337(5) . ? C9 C10 1.405(5) . ? C10 C11 1.377(4) . ? C11 C12 1.415(3) . ? C13 C18 1.387(3) . ? C13 C14 1.388(3) . ? C14 C15 1.370(3) . ? C15 C16 1.378(3) . ? C16 C17 1.366(3) . ? C17 C18 1.385(3) . ? C20 C21 1.380(3) . ? C20 C25 1.382(4) . ? C21 C22 1.370(4) . ? C22 C23 1.359(5) . ? C23 C24 1.379(4) . ? C24 C25 1.383(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 C2 116.72(18) . . ? N1 C1 C20 116.34(19) . . ? N1 C1 C19 105.9(2) . . ? C20 C1 C19 112.7(2) . . ? N1 C2 C3 110.81(17) . . ? N1 C2 C13 108.62(17) . . ? C3 C2 C13 109.70(16) . . ? C4 C3 C12 118.3(2) . . ? C4 C3 C2 121.61(19) . . ? C12 C3 C2 119.79(19) . . ? O1 C4 C3 124.0(2) . . ? O1 C4 C5 114.7(2) . . ? C3 C4 C5 121.4(2) . . ? C6 C5 C4 120.7(3) . . ? C5 C6 C7 121.4(3) . . ? C8 C7 C6 122.1(3) . . ? C8 C7 C12 119.1(3) . . ? C6 C7 C12 118.9(3) . . ? C9 C8 C7 122.2(3) . . ? C8 C9 C10 120.2(3) . . ? C11 C10 C9 119.7(3) . . ? C10 C11 C12 121.6(3) . . ? C11 C12 C7 117.2(2) . . ? C11 C12 C3 123.5(2) . . ? C7 C12 C3 119.3(2) . . ? C18 C13 C14 117.70(19) . . ? C18 C13 C2 121.05(19) . . ? C14 C13 C2 121.21(18) . . ? C15 C14 C13 122.0(2) . . ? C14 C15 C16 118.4(2) . . ? C17 C16 C15 121.8(2) . . ? C17 C16 Br1 118.88(17) . . ? C15 C16 Br1 119.18(17) . . ? C16 C17 C18 118.8(2) . . ? C17 C18 C13 121.2(2) . . ? C21 C20 C25 117.7(2) . . ? C21 C20 C1 121.2(2) . . ? C25 C20 C1 121.0(2) . . ? C22 C21 C20 121.2(3) . . ? C23 C22 C21 120.8(3) . . ? C22 C23 C24 119.5(3) . . ? C23 C24 C25 119.7(3) . . ? C20 C25 C24 121.1(3) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1 H4 N1 0.82 1.85 2.577(3) 147.4 . C9 H9 Br1 0.93 2.98 3.471(3) 114.8 4_747 C15 H15 O1 0.93 2.53 3.296(3) 139.9 3_567 _diffrn_measured_fraction_theta_max 0.938 _diffrn_reflns_theta_full 29.02 _diffrn_measured_fraction_theta_full 0.938 _refine_diff_density_max 0.637 _refine_diff_density_min -0.238 _refine_diff_density_rms 0.046 # Attachment '- g11.cif' data_g11 _database_code_depnum_ccdc_archive 'CCDC 822818' #TrackingRef '- g11.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C29 H24 F N O' _chemical_formula_sum 'C29 H24 F N O' _chemical_formula_weight 421.49 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' O O 0.0106 0.0060 '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 orthorhombic _symmetry_space_group_name_H-M P212121 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' _cell_length_a 8.2095(5) _cell_length_b 14.0391(8) _cell_length_c 19.7711(12) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2278.7(2) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 108 _cell_measurement_theta_min 3.11 _cell_measurement_theta_max 20.57 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.229 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 888 _exptl_absorpt_coefficient_mu 0.079 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9689 _exptl_absorpt_correction_T_max 0.9843 _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 'Nonius Kappa CCD' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15886 _diffrn_reflns_av_R_equivalents 0.0243 _diffrn_reflns_av_sigmaI/netI 0.0321 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 1.78 _diffrn_reflns_theta_max 29.06 _reflns_number_total 5561 _reflns_number_gt 4185 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius, 1998)' _computing_data_reduction 'EVALCCD (Duisenberg et al., 2003)' _computing_cell_refinement 'EVALCCD (Duisenberg et al., 2003)' _computing_structure_solution 'SIR97 (Altomare et al. 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'DIAMOND 2.1e (1998-2001 Crystal Impact GbR)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0512P)^2^+0.0679P] 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 0.0(10) _refine_ls_number_reflns 5561 _refine_ls_number_parameters 293 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0662 _refine_ls_R_factor_gt 0.0460 _refine_ls_wR_factor_ref 0.1080 _refine_ls_wR_factor_gt 0.0994 _refine_ls_goodness_of_fit_ref 1.032 _refine_ls_restrained_S_all 1.032 _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 F1 F 0.88955(17) 0.44756(11) 0.54157(6) 0.0947(5) Uani 1 1 d . . . O1 O 0.19542(16) 0.42938(12) 0.76146(8) 0.0754(4) Uani 1 1 d . . . H4 H 0.2507 0.3820 0.7537 0.113 Uiso 1 1 calc R . . N1 N 0.43343(18) 0.31255(11) 0.77364(7) 0.0500(3) Uani 1 1 d . . . C1 C 0.5444(2) 0.39481(12) 0.78494(8) 0.0464(4) Uani 1 1 d . . . H1 H 0.6228 0.3769 0.8201 0.056 Uiso 1 1 calc R . . C2 C 0.3937(2) 0.25645(12) 0.83402(9) 0.0468(4) Uani 1 1 d . . . H2 H 0.3534 0.3007 0.8685 0.056 Uiso 1 1 calc R . . C3 C 0.4491(2) 0.48177(13) 0.81005(8) 0.0516(4) Uani 1 1 d . . . C4 C 0.2845(3) 0.49278(15) 0.79724(10) 0.0607(5) Uani 1 1 d . . . C5 C 0.1981(3) 0.57267(19) 0.82151(12) 0.0785(7) Uani 1 1 d . . . H5 H 0.0872 0.5783 0.8127 0.094 Uiso 1 1 calc R . . C6 C 0.2749(4) 0.64079(19) 0.85728(12) 0.0840(8) Uani 1 1 d . . . H6 H 0.2156 0.6925 0.8734 0.101 Uiso 1 1 calc R . . C7 C 0.4445(3) 0.63553(15) 0.87103(10) 0.0732(6) Uani 1 1 d . . . C8 C 0.5280(5) 0.70774(17) 0.90719(14) 0.0967(9) Uani 1 1 d . . . H8 H 0.4699 0.7600 0.9231 0.116 Uiso 1 1 calc R . . C9 C 0.6884(5) 0.7028(2) 0.91903(14) 0.0991(9) Uani 1 1 d . . . H9 H 0.7410 0.7518 0.9419 0.119 Uiso 1 1 calc R . . C10 C 0.7763(3) 0.62340(19) 0.89684(12) 0.0852(7) Uani 1 1 d . . . H10 H 0.8871 0.6190 0.9060 0.102 Uiso 1 1 calc R . . C11 C 0.7007(3) 0.55239(15) 0.86184(10) 0.0672(5) Uani 1 1 d . . . H11 H 0.7620 0.5008 0.8470 0.081 Uiso 1 1 calc R . . C12 C 0.5316(3) 0.55460(13) 0.84730(9) 0.0569(5) Uani 1 1 d . . . C13 C 0.6387(2) 0.41324(11) 0.71973(8) 0.0463(4) Uani 1 1 d . . . C14 C 0.8040(2) 0.39553(15) 0.71641(10) 0.0604(5) Uani 1 1 d . . . H14 H 0.8589 0.3755 0.7550 0.072 Uiso 1 1 calc R . . C15 C 0.8891(2) 0.40714(16) 0.65664(11) 0.0688(6) Uani 1 1 d . . . H15 H 1.0005 0.3956 0.6548 0.083 Uiso 1 1 calc R . . C16 C 0.8064(3) 0.43579(15) 0.60068(10) 0.0637(5) Uani 1 1 d . . . C17 C 0.6434(3) 0.45436(13) 0.60094(9) 0.0578(5) Uani 1 1 d . . . H17 H 0.5900 0.4734 0.5617 0.069 Uiso 1 1 calc R . . C18 C 0.5596(2) 0.44409(12) 0.66130(8) 0.0531(4) Uani 1 1 d . . . H18 H 0.4489 0.4580 0.6629 0.064 Uiso 1 1 calc R . . C19 C 0.2540(2) 0.18954(15) 0.81596(12) 0.0671(6) Uani 1 1 d . . . H19A H 0.1658 0.2257 0.7971 0.101 Uiso 1 1 calc R . . H19B H 0.2174 0.1573 0.8560 0.101 Uiso 1 1 calc R . . H19C H 0.2910 0.1436 0.7835 0.101 Uiso 1 1 calc R . . C20 C 0.5363(2) 0.20183(11) 0.86482(8) 0.0417(4) Uani 1 1 d . . . C21 C 0.6685(2) 0.17629(12) 0.82660(9) 0.0495(4) Uani 1 1 d . . . H21 H 0.6734 0.1959 0.7817 0.059 Uiso 1 1 calc R . . C22 C 0.7966(2) 0.12153(14) 0.85299(9) 0.0570(5) Uani 1 1 d . . . H22 H 0.8846 0.1056 0.8256 0.068 Uiso 1 1 calc R . . C23 C 0.7926(2) 0.09186(14) 0.91808(10) 0.0568(5) Uani 1 1 d . . . H23 H 0.8779 0.0554 0.9351 0.068 Uiso 1 1 calc R . . C24 C 0.6604(2) 0.11559(12) 0.96047(8) 0.0468(4) Uani 1 1 d . . . C25 C 0.6541(2) 0.08495(13) 1.02856(9) 0.0583(5) Uani 1 1 d . . . H25 H 0.7381 0.0477 1.0458 0.070 Uiso 1 1 calc R . . C26 C 0.5276(3) 0.10897(14) 1.06915(9) 0.0638(5) Uani 1 1 d . . . H26 H 0.5262 0.0892 1.1140 0.077 Uiso 1 1 calc R . . C27 C 0.3997(3) 0.16323(14) 1.04368(10) 0.0647(5) Uani 1 1 d . . . H27 H 0.3126 0.1789 1.0716 0.078 Uiso 1 1 calc R . . C28 C 0.4005(2) 0.19369(12) 0.97813(9) 0.0540(4) Uani 1 1 d . . . H28 H 0.3135 0.2297 0.9621 0.065 Uiso 1 1 calc R . . C29 C 0.5310(2) 0.17166(11) 0.93400(8) 0.0427(4) Uani 1 1 d . . . H1N H 0.478(2) 0.2779(12) 0.7414(10) 0.051 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 F1 0.0932(9) 0.1294(11) 0.0614(7) -0.0145(7) 0.0229(6) -0.0459(9) O1 0.0505(8) 0.0953(11) 0.0804(10) 0.0281(9) -0.0057(7) 0.0099(8) N1 0.0519(8) 0.0544(9) 0.0437(8) 0.0073(7) -0.0013(7) -0.0006(7) C1 0.0459(9) 0.0499(10) 0.0435(9) 0.0086(7) -0.0033(7) 0.0048(8) C2 0.0475(9) 0.0470(9) 0.0460(9) 0.0054(7) 0.0028(7) 0.0028(8) C3 0.0548(11) 0.0532(10) 0.0467(9) 0.0152(8) 0.0090(8) 0.0111(9) C4 0.0563(11) 0.0724(13) 0.0532(11) 0.0278(9) 0.0095(9) 0.0134(10) C5 0.0707(14) 0.0948(18) 0.0700(14) 0.0388(13) 0.0244(12) 0.0386(14) C6 0.109(2) 0.0728(16) 0.0701(15) 0.0263(12) 0.0368(14) 0.0463(15) C7 0.1053(18) 0.0554(12) 0.0588(12) 0.0167(10) 0.0285(12) 0.0264(13) C8 0.161(3) 0.0510(14) 0.0777(16) 0.0014(11) 0.0376(18) 0.0210(17) C9 0.147(3) 0.0681(17) 0.0822(17) -0.0161(13) 0.0232(19) -0.0172(18) C10 0.1015(17) 0.0810(17) 0.0731(15) -0.0168(12) 0.0110(13) -0.0148(15) C11 0.0812(14) 0.0610(12) 0.0593(12) -0.0059(9) 0.0110(11) 0.0024(11) C12 0.0717(13) 0.0512(10) 0.0477(10) 0.0124(8) 0.0159(9) 0.0119(10) C13 0.0493(9) 0.0410(8) 0.0485(9) 0.0023(7) 0.0029(8) 0.0012(7) C14 0.0476(10) 0.0743(13) 0.0593(11) -0.0012(9) -0.0045(9) 0.0022(9) C15 0.0467(10) 0.0899(15) 0.0699(13) -0.0133(11) 0.0091(10) -0.0106(10) C16 0.0697(13) 0.0696(13) 0.0519(11) -0.0110(9) 0.0128(10) -0.0284(11) C17 0.0758(13) 0.0484(10) 0.0493(10) 0.0048(8) 0.0002(9) -0.0064(10) C18 0.0562(10) 0.0493(10) 0.0538(10) 0.0087(8) 0.0017(9) 0.0051(8) C19 0.0508(11) 0.0697(13) 0.0808(15) 0.0198(11) -0.0075(9) -0.0046(9) C20 0.0468(9) 0.0371(8) 0.0413(8) -0.0028(7) 0.0001(7) 0.0009(7) C21 0.0532(10) 0.0534(10) 0.0420(9) -0.0056(8) 0.0044(8) 0.0028(8) C22 0.0469(10) 0.0608(11) 0.0635(12) -0.0118(9) 0.0041(9) 0.0096(9) C23 0.0481(10) 0.0564(11) 0.0660(12) -0.0052(9) -0.0094(9) 0.0114(9) C24 0.0472(9) 0.0407(9) 0.0526(10) -0.0027(7) -0.0073(7) -0.0021(7) C25 0.0637(11) 0.0526(11) 0.0587(11) 0.0099(9) -0.0160(9) 0.0001(9) C26 0.0786(14) 0.0663(12) 0.0465(10) 0.0123(9) -0.0014(10) -0.0028(11) C27 0.0796(14) 0.0644(12) 0.0502(11) 0.0081(9) 0.0159(10) 0.0081(11) C28 0.0613(11) 0.0487(10) 0.0518(10) 0.0060(8) 0.0064(8) 0.0125(9) C29 0.0468(9) 0.0352(8) 0.0461(9) -0.0027(6) -0.0004(7) 0.0010(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag F1 C16 1.363(2) . ? O1 C4 1.352(3) . ? N1 C2 1.467(2) . ? N1 C1 1.488(2) . ? C1 C13 1.526(2) . ? C1 C3 1.533(2) . ? C2 C19 1.524(3) . ? C2 C20 1.526(2) . ? C3 C4 1.384(3) . ? C3 C12 1.430(3) . ? C4 C5 1.411(3) . ? C5 C6 1.346(4) . ? C6 C7 1.420(4) . ? C7 C8 1.417(4) . ? C7 C12 1.422(3) . ? C8 C9 1.339(4) . ? C9 C10 1.398(4) . ? C10 C11 1.363(3) . ? C11 C12 1.418(3) . ? C13 C14 1.381(2) . ? C13 C18 1.394(2) . ? C14 C15 1.382(3) . ? C15 C16 1.359(3) . ? C16 C17 1.364(3) . ? C17 C18 1.385(2) . ? C20 C21 1.370(2) . ? C20 C29 1.432(2) . ? C21 C22 1.404(2) . ? C22 C23 1.353(3) . ? C23 C24 1.411(2) . ? C24 C25 1.414(2) . ? C24 C29 1.422(2) . ? C25 C26 1.355(3) . ? C26 C27 1.392(3) . ? C27 C28 1.365(2) . ? C28 C29 1.416(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 N1 C1 115.52(13) . . ? N1 C1 C13 108.38(13) . . ? N1 C1 C3 110.75(14) . . ? C13 C1 C3 113.42(13) . . ? N1 C2 C19 107.91(15) . . ? N1 C2 C20 115.07(14) . . ? C19 C2 C20 111.14(14) . . ? C4 C3 C12 118.46(18) . . ? C4 C3 C1 121.89(18) . . ? C12 C3 C1 119.65(16) . . ? O1 C4 C3 123.41(19) . . ? O1 C4 C5 115.4(2) . . ? C3 C4 C5 121.2(2) . . ? C6 C5 C4 120.5(2) . . ? C5 C6 C7 121.5(2) . . ? C8 C7 C6 122.2(2) . . ? C8 C7 C12 119.7(3) . . ? C6 C7 C12 118.1(2) . . ? C9 C8 C7 121.8(3) . . ? C8 C9 C10 119.6(3) . . ? C11 C10 C9 120.5(3) . . ? C10 C11 C12 122.2(2) . . ? C11 C12 C7 116.3(2) . . ? C11 C12 C3 123.50(18) . . ? C7 C12 C3 120.2(2) . . ? C14 C13 C18 118.31(17) . . ? C14 C13 C1 120.53(16) . . ? C18 C13 C1 121.10(16) . . ? C13 C14 C15 121.06(19) . . ? C16 C15 C14 118.59(18) . . ? C15 C16 F1 118.94(19) . . ? C15 C16 C17 122.93(18) . . ? F1 C16 C17 118.1(2) . . ? C16 C17 C18 118.10(19) . . ? C17 C18 C13 120.99(18) . . ? C21 C20 C29 118.24(15) . . ? C21 C20 C2 121.27(15) . . ? C29 C20 C2 120.41(14) . . ? C20 C21 C22 122.15(16) . . ? C23 C22 C21 120.25(17) . . ? C22 C23 C24 120.74(17) . . ? C23 C24 C25 121.47(16) . . ? C23 C24 C29 119.11(15) . . ? C25 C24 C29 119.42(16) . . ? C26 C25 C24 121.07(18) . . ? C25 C26 C27 120.02(17) . . ? C28 C27 C26 120.77(19) . . ? C27 C28 C29 121.35(17) . . ? C28 C29 C24 117.35(15) . . ? C28 C29 C20 123.14(15) . . ? C24 C29 C20 119.50(15) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1 H4 N1 0.82 1.83 2.562(2) 147.6 . C23 H23 F1 0.93 2.48 3.398(2) 169.3 3_746 C15 H15 O1 0.93 2.69 3.274(3) 121.6 1_655 _diffrn_measured_fraction_theta_max 0.946 _diffrn_reflns_theta_full 29.06 _diffrn_measured_fraction_theta_full 0.946 _refine_diff_density_max 0.129 _refine_diff_density_min -0.149 _refine_diff_density_rms 0.026 # Attachment '- ff4.cif' data_ff4 _database_code_depnum_ccdc_archive 'CCDC 822819' #TrackingRef '- ff4.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C29 H24 Cl N O' _chemical_formula_sum 'C29 H24 Cl N O' _chemical_formula_weight 437.94 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' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M P212121 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 10.7520(7) _cell_length_b 13.3730(17) _cell_length_c 16.005(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2301.3(5) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 147 _cell_measurement_theta_min 3.95 _cell_measurement_theta_max 20.03 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.55 _exptl_crystal_size_mid 0.50 _exptl_crystal_size_min 0.45 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.264 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 920 _exptl_absorpt_coefficient_mu 0.187 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9039 _exptl_absorpt_correction_T_max 0.9204 _exptl_absorpt_process_details SADABS _exptl_special_details ; Sheldrick, G. M. SADABS, Absorption Correction Program. University of G ttingen, Germany, 1996. ; _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 'Nonius Kappa CCD' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16091 _diffrn_reflns_av_R_equivalents 0.0738 _diffrn_reflns_av_sigmaI/netI 0.0754 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 5.03 _diffrn_reflns_theta_max 27.50 _reflns_number_total 5123 _reflns_number_gt 3051 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius, 1998)' _computing_data_reduction 'EVALCCD (Duisenberg et al., 2003)' _computing_cell_refinement 'EVALCCD (Duisenberg et al., 2003)' _computing_structure_solution 'SIR97 (Altomare et al. 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'DIAMOND 2.1e (1998-2001 Crystal Impact GbR)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0401P)^2^+0.2444P] 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 -0.01(9) _refine_ls_number_reflns 5123 _refine_ls_number_parameters 293 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1217 _refine_ls_R_factor_gt 0.0579 _refine_ls_wR_factor_ref 0.1191 _refine_ls_wR_factor_gt 0.0968 _refine_ls_goodness_of_fit_ref 1.062 _refine_ls_restrained_S_all 1.062 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl -0.16747(11) 0.19500(8) -0.14264(9) 0.0992(4) Uani 1 1 d . . . O1 O 0.4327(2) 0.08430(17) 0.07372(16) 0.0627(6) Uani 1 1 d . . . H4 H 0.3680 0.0926 0.0999 0.094 Uiso 1 1 calc R . . N1 N 0.2274(2) 0.02689(18) 0.14610(15) 0.0425(6) Uani 1 1 d . . . H1N H 0.158(3) 0.054(2) 0.1648(19) 0.051 Uiso 1 1 d . . . C1 C 0.2850(3) -0.0289(2) 0.21610(17) 0.0416(7) Uani 1 1 d . . . H1 H 0.3616 -0.0594 0.1949 0.050 Uiso 1 1 calc R . . C2 C 0.1992(2) -0.0331(2) 0.07044(16) 0.0362(6) Uani 1 1 d . . . H2 H 0.1590 -0.0955 0.0879 0.043 Uiso 1 1 calc R . . C3 C 0.3186(2) -0.0592(2) 0.02329(17) 0.0392(6) Uani 1 1 d . . . C4 C 0.4245(3) -0.0005(2) 0.02827(19) 0.0449(7) Uani 1 1 d . . . C5 C 0.5336(3) -0.0268(3) -0.0153(2) 0.0586(9) Uani 1 1 d . . . H5 H 0.6050 0.0117 -0.0086 0.070 Uiso 1 1 calc R . . C6 C 0.5364(3) -0.1070(3) -0.0667(2) 0.0620(9) Uani 1 1 d . . . H6 H 0.6092 -0.1227 -0.0953 0.074 Uiso 1 1 calc R . . C7 C 0.4295(3) -0.1674(2) -0.07749(19) 0.0498(8) Uani 1 1 d . . . C8 C 0.4286(4) -0.2484(3) -0.1340(2) 0.0664(10) Uani 1 1 d . . . H8 H 0.5003 -0.2633 -0.1640 0.080 Uiso 1 1 calc R . . C9 C 0.3255(5) -0.3046(3) -0.1454(2) 0.0725(11) Uani 1 1 d . . . H9 H 0.3262 -0.3564 -0.1841 0.087 Uiso 1 1 calc R . . C10 C 0.2187(4) -0.2851(3) -0.0994(2) 0.0641(10) Uani 1 1 d . . . H10 H 0.1486 -0.3249 -0.1068 0.077 Uiso 1 1 calc R . . C11 C 0.2160(3) -0.2073(2) -0.04305(17) 0.0483(8) Uani 1 1 d . . . H11 H 0.1441 -0.1960 -0.0122 0.058 Uiso 1 1 calc R . . C12 C 0.3200(3) -0.1444(2) -0.03107(17) 0.0406(7) Uani 1 1 d . . . C13 C 0.1078(2) 0.0261(2) 0.01682(17) 0.0382(6) Uani 1 1 d . . . C14 C 0.1409(3) 0.1156(2) -0.02077(18) 0.0443(7) Uani 1 1 d . . . H14 H 0.2211 0.1402 -0.0138 0.053 Uiso 1 1 calc R . . C15 C 0.0559(3) 0.1692(2) -0.0688(2) 0.0504(8) Uani 1 1 d . . . H15 H 0.0786 0.2294 -0.0935 0.060 Uiso 1 1 calc R . . C16 C -0.0618(3) 0.1317(2) -0.0788(2) 0.0559(8) Uani 1 1 d . . . C17 C -0.0970(3) 0.0445(3) -0.0423(2) 0.0630(10) Uani 1 1 d . . . H17 H -0.1771 0.0201 -0.0500 0.076 Uiso 1 1 calc R . . C18 C -0.0123(3) -0.0082(2) 0.0069(2) 0.0520(8) Uani 1 1 d . . . H18 H -0.0370 -0.0670 0.0332 0.062 Uiso 1 1 calc R . . C19 C 0.3222(4) 0.0481(2) 0.28174(19) 0.0634(9) Uani 1 1 d . . . H19A H 0.3719 0.0993 0.2561 0.095 Uiso 1 1 calc R . . H19B H 0.3694 0.0160 0.3250 0.095 Uiso 1 1 calc R . . H19C H 0.2488 0.0776 0.3054 0.095 Uiso 1 1 calc R . . C20 C 0.2062(3) -0.1126(2) 0.25419(16) 0.0410(7) Uani 1 1 d . . . C21 C 0.1042(3) -0.0894(3) 0.3005(2) 0.0571(9) Uani 1 1 d . . . H21 H 0.0782 -0.0231 0.3032 0.069 Uiso 1 1 calc R . . C22 C 0.0367(3) -0.1629(3) 0.3445(2) 0.0724(11) Uani 1 1 d . . . H22 H -0.0342 -0.1452 0.3743 0.087 Uiso 1 1 calc R . . C23 C 0.0751(4) -0.2596(3) 0.3435(2) 0.0729(11) Uani 1 1 d . . . H23 H 0.0333 -0.3070 0.3754 0.087 Uiso 1 1 calc R . . C24 C 0.1771(3) -0.2888(2) 0.2949(2) 0.0593(9) Uani 1 1 d . . . C25 C 0.2162(5) -0.3897(3) 0.2900(3) 0.0920(14) Uani 1 1 d . . . H25 H 0.1758 -0.4379 0.3220 0.110 Uiso 1 1 calc R . . C26 C 0.3107(5) -0.4173(3) 0.2399(4) 0.1056(16) Uani 1 1 d . . . H26 H 0.3348 -0.4840 0.2378 0.127 Uiso 1 1 calc R . . C27 C 0.3725(4) -0.3472(3) 0.1914(3) 0.0866(13) Uani 1 1 d . . . H27 H 0.4359 -0.3674 0.1557 0.104 Uiso 1 1 calc R . . C28 C 0.3407(3) -0.2496(3) 0.1959(2) 0.0602(9) Uani 1 1 d . . . H28 H 0.3846 -0.2035 0.1639 0.072 Uiso 1 1 calc R . . C29 C 0.2429(3) -0.2151(2) 0.24782(17) 0.0444(7) 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 Cl1 0.0933(8) 0.0761(7) 0.1283(10) 0.0001(7) -0.0595(7) 0.0234(6) O1 0.0609(15) 0.0623(14) 0.0650(16) -0.0030(13) -0.0009(12) -0.0177(12) N1 0.0502(14) 0.0455(14) 0.0319(13) -0.0056(11) -0.0007(11) 0.0042(12) C1 0.0460(17) 0.0457(16) 0.0332(15) 0.0009(13) -0.0011(12) -0.0032(13) C2 0.0415(15) 0.0372(14) 0.0299(14) -0.0019(12) 0.0037(12) -0.0023(12) C3 0.0399(16) 0.0427(16) 0.0350(15) 0.0082(13) 0.0001(12) 0.0048(13) C4 0.0481(17) 0.0456(18) 0.0409(17) 0.0076(15) -0.0012(14) 0.0015(14) C5 0.0372(17) 0.079(2) 0.060(2) 0.016(2) 0.0024(15) 0.0020(16) C6 0.046(2) 0.084(3) 0.056(2) 0.014(2) 0.0139(16) 0.0256(18) C7 0.058(2) 0.0521(19) 0.0392(17) 0.0114(15) 0.0073(15) 0.0248(16) C8 0.082(3) 0.068(2) 0.050(2) 0.0062(19) 0.018(2) 0.036(2) C9 0.122(3) 0.047(2) 0.048(2) -0.0038(17) 0.004(2) 0.023(2) C10 0.095(3) 0.051(2) 0.046(2) -0.0055(16) 0.0017(19) -0.0045(19) C11 0.068(2) 0.0426(17) 0.0342(17) -0.0008(14) 0.0087(14) -0.0006(15) C12 0.0531(17) 0.0407(16) 0.0281(15) 0.0086(13) 0.0040(13) 0.0082(14) C13 0.0395(15) 0.0452(16) 0.0300(15) -0.0030(13) 0.0050(11) 0.0022(13) C14 0.0455(17) 0.0465(18) 0.0408(17) 0.0041(15) -0.0013(13) -0.0012(14) C15 0.062(2) 0.0437(17) 0.0457(18) 0.0014(15) -0.0053(15) 0.0043(15) C16 0.054(2) 0.055(2) 0.059(2) -0.0040(17) -0.0194(16) 0.0141(16) C17 0.0397(17) 0.069(2) 0.080(3) -0.001(2) -0.0109(17) 0.0005(17) C18 0.0447(18) 0.054(2) 0.057(2) 0.0033(16) 0.0028(14) -0.0060(15) C19 0.088(3) 0.063(2) 0.0388(18) -0.0006(16) -0.0143(18) -0.0251(19) C20 0.0464(17) 0.0507(17) 0.0258(14) -0.0075(13) -0.0023(13) -0.0044(14) C21 0.060(2) 0.058(2) 0.053(2) -0.0163(17) 0.0161(16) -0.0073(16) C22 0.069(2) 0.093(3) 0.055(2) -0.020(2) 0.0277(19) -0.025(2) C23 0.096(3) 0.073(3) 0.050(2) -0.0024(19) 0.013(2) -0.038(2) C24 0.076(2) 0.058(2) 0.043(2) 0.0032(16) -0.0082(17) -0.0153(19) C25 0.132(4) 0.050(2) 0.093(3) 0.014(2) -0.005(3) -0.016(3) C26 0.135(4) 0.058(3) 0.124(4) -0.001(3) -0.018(4) 0.027(3) C27 0.083(3) 0.064(3) 0.112(4) -0.003(3) -0.002(3) 0.023(2) C28 0.056(2) 0.056(2) 0.068(2) -0.0052(17) -0.0039(18) 0.0119(17) C29 0.0494(17) 0.0503(18) 0.0334(16) 0.0009(14) -0.0092(13) -0.0038(14) _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 C16 1.747(3) . ? O1 C4 1.351(3) . ? O1 H4 0.8200 . ? N1 C1 1.482(4) . ? N1 C2 1.484(3) . ? N1 H1N 0.88(3) . ? C1 C19 1.525(4) . ? C1 C20 1.530(4) . ? C1 H1 0.9800 . ? C2 C13 1.527(4) . ? C2 C3 1.529(3) . ? C2 H2 0.9800 . ? C3 C4 1.386(4) . ? C3 C12 1.434(4) . ? C4 C5 1.410(4) . ? C5 C6 1.353(5) . ? C5 H5 0.9300 . ? C6 C7 1.415(4) . ? C6 H6 0.9300 . ? C7 C8 1.410(5) . ? C7 C12 1.426(4) . ? C8 C9 1.351(5) . ? C8 H8 0.9300 . ? C9 C10 1.389(5) . ? C9 H9 0.9300 . ? C10 C11 1.378(4) . ? C10 H10 0.9300 . ? C11 C12 1.413(4) . ? C11 H11 0.9300 . ? C13 C18 1.380(4) . ? C13 C14 1.385(4) . ? C14 C15 1.392(4) . ? C14 H14 0.9300 . ? C15 C16 1.371(4) . ? C15 H15 0.9300 . ? C16 C17 1.358(4) . ? C17 C18 1.395(4) . ? C17 H17 0.9300 . ? C18 H18 0.9300 . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? C20 C21 1.360(4) . ? C20 C29 1.430(4) . ? C21 C22 1.411(5) . ? C21 H21 0.9300 . ? C22 C23 1.357(5) . ? C22 H22 0.9300 . ? C23 C24 1.400(5) . ? C23 H23 0.9300 . ? C24 C25 1.416(5) . ? C24 C29 1.427(4) . ? C25 C26 1.345(6) . ? C25 H25 0.9300 . ? C26 C27 1.387(6) . ? C26 H26 0.9300 . ? C27 C28 1.350(5) . ? C27 H27 0.9300 . ? C28 C29 1.418(4) . ? C28 H28 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C4 O1 H4 109.5 . . ? C1 N1 C2 115.5(2) . . ? C1 N1 H1N 108(2) . . ? C2 N1 H1N 109.0(19) . . ? N1 C1 C19 106.9(2) . . ? N1 C1 C20 116.0(2) . . ? C19 C1 C20 111.4(2) . . ? N1 C1 H1 107.4 . . ? C19 C1 H1 107.4 . . ? C20 C1 H1 107.4 . . ? N1 C2 C13 108.0(2) . . ? N1 C2 C3 110.8(2) . . ? C13 C2 C3 112.4(2) . . ? N1 C2 H2 108.5 . . ? C13 C2 H2 108.5 . . ? C3 C2 H2 108.5 . . ? C4 C3 C12 118.4(3) . . ? C4 C3 C2 122.2(2) . . ? C12 C3 C2 119.3(2) . . ? O1 C4 C3 124.1(3) . . ? O1 C4 C5 114.9(3) . . ? C3 C4 C5 121.0(3) . . ? C6 C5 C4 121.1(3) . . ? C6 C5 H5 119.4 . . ? C4 C5 H5 119.4 . . ? C5 C6 C7 120.6(3) . . ? C5 C6 H6 119.7 . . ? C7 C6 H6 119.7 . . ? C8 C7 C6 121.5(3) . . ? C8 C7 C12 119.6(3) . . ? C6 C7 C12 118.9(3) . . ? C9 C8 C7 121.3(3) . . ? C9 C8 H8 119.3 . . ? C7 C8 H8 119.3 . . ? C8 C9 C10 120.2(3) . . ? C8 C9 H9 119.9 . . ? C10 C9 H9 119.9 . . ? C11 C10 C9 120.4(3) . . ? C11 C10 H10 119.8 . . ? C9 C10 H10 119.8 . . ? C10 C11 C12 121.5(3) . . ? C10 C11 H11 119.3 . . ? C12 C11 H11 119.3 . . ? C11 C12 C7 117.0(3) . . ? C11 C12 C3 123.2(3) . . ? C7 C12 C3 119.8(3) . . ? C18 C13 C14 118.5(3) . . ? C18 C13 C2 119.6(3) . . ? C14 C13 C2 121.8(2) . . ? C13 C14 C15 121.1(3) . . ? C13 C14 H14 119.5 . . ? C15 C14 H14 119.5 . . ? C16 C15 C14 118.8(3) . . ? C16 C15 H15 120.6 . . ? C14 C15 H15 120.6 . . ? C17 C16 C15 121.4(3) . . ? C17 C16 Cl1 119.1(3) . . ? C15 C16 Cl1 119.5(3) . . ? C16 C17 C18 119.7(3) . . ? C16 C17 H17 120.2 . . ? C18 C17 H17 120.2 . . ? C13 C18 C17 120.5(3) . . ? C13 C18 H18 119.8 . . ? C17 C18 H18 119.8 . . ? C1 C19 H19A 109.5 . . ? C1 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C1 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C21 C20 C29 118.7(3) . . ? C21 C20 C1 119.8(3) . . ? C29 C20 C1 121.3(2) . . ? C20 C21 C22 121.9(3) . . ? C20 C21 H21 119.1 . . ? C22 C21 H21 119.1 . . ? C23 C22 C21 120.1(3) . . ? C23 C22 H22 120.0 . . ? C21 C22 H22 120.0 . . ? C22 C23 C24 120.7(3) . . ? C22 C23 H23 119.6 . . ? C24 C23 H23 119.6 . . ? C23 C24 C25 121.9(4) . . ? C23 C24 C29 119.3(3) . . ? C25 C24 C29 118.8(4) . . ? C26 C25 C24 121.2(4) . . ? C26 C25 H25 119.4 . . ? C24 C25 H25 119.4 . . ? C25 C26 C27 120.7(4) . . ? C25 C26 H26 119.7 . . ? C27 C26 H26 119.7 . . ? C28 C27 C26 120.1(4) . . ? C28 C27 H27 119.9 . . ? C26 C27 H27 119.9 . . ? C27 C28 C29 122.2(4) . . ? C27 C28 H28 118.9 . . ? C29 C28 H28 118.9 . . ? C28 C29 C24 116.9(3) . . ? C28 C29 C20 123.9(3) . . ? C24 C29 C20 119.2(3) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1 H4 N1 0.82 1.90 2.609(3) 144.3 . O1 H4 Cl1 0.82 2.95 3.330(3) 111.1 3 C15 H15 O1 0.93 2.96 3.553(4) 122.9 3_455 _diffrn_measured_fraction_theta_max 0.975 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.975 _refine_diff_density_max 0.167 _refine_diff_density_min -0.272 _refine_diff_density_rms 0.038 # Attachment '- ff3.cif' data_ff3 _database_code_depnum_ccdc_archive 'CCDC 822820' #TrackingRef '- ff3.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C29 H24 Br N O' _chemical_formula_sum 'C29 H24 Br N O' _chemical_formula_weight 482.40 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 '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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M P212121 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 10.7830(5) _cell_length_b 13.4940(19) _cell_length_c 15.938(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2319.1(5) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 144 _cell_measurement_theta_min 4.32 _cell_measurement_theta_max 18.49 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.55 _exptl_crystal_size_mid 0.50 _exptl_crystal_size_min 0.50 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.382 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 992 _exptl_absorpt_coefficient_mu 1.794 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.4387 _exptl_absorpt_correction_T_max 0.4674 _exptl_absorpt_process_details SADABS _exptl_special_details ; Sheldrick, G. M. SADABS, Absorption Correction Program. University of G ttingen, Germany, 1996. ; _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 'Nonius Kappa CCD' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 21983 _diffrn_reflns_av_R_equivalents 0.0708 _diffrn_reflns_av_sigmaI/netI 0.0862 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 5.01 _diffrn_reflns_theta_max 27.50 _reflns_number_total 5188 _reflns_number_gt 3003 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius, 1998)' _computing_data_reduction 'EVALCCD (Duisenberg et al., 2003)' _computing_cell_refinement 'EVALCCD (Duisenberg et al., 2003)' _computing_structure_solution 'SIR97 (Altomare et al. 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'DIAMOND 2.1e (1998-2001 Crystal Impact GbR)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0529P)^2^+0.0290P] 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 0.046(12) _refine_ls_number_reflns 5188 _refine_ls_number_parameters 293 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1258 _refine_ls_R_factor_gt 0.0517 _refine_ls_wR_factor_ref 0.1264 _refine_ls_wR_factor_gt 0.1021 _refine_ls_goodness_of_fit_ref 1.088 _refine_ls_restrained_S_all 1.088 _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 Br1 Br -0.17297(6) 0.19379(5) -0.14648(5) 0.0930(3) Uani 1 1 d . . . O1 O 0.4357(3) 0.0828(2) 0.0757(2) 0.0621(9) Uani 1 1 d . . . H4 H 0.3682 0.0947 0.0972 0.093 Uiso 1 1 calc R . . N1 N 0.2317(3) 0.0247(2) 0.1489(2) 0.0429(8) Uani 1 1 d . . . H1N H 0.162(4) 0.056(3) 0.164(3) 0.051 Uiso 1 1 d . . . C1 C 0.2883(3) -0.0293(3) 0.2190(2) 0.0411(9) Uani 1 1 d . . . H1 H 0.3652 -0.0592 0.1981 0.049 Uiso 1 1 calc R . . C2 C 0.2047(3) -0.0339(3) 0.0724(2) 0.0384(9) Uani 1 1 d . . . H2 H 0.1654 -0.0961 0.0897 0.046 Uiso 1 1 calc R . . C3 C 0.3229(3) -0.0595(3) 0.0242(2) 0.0385(8) Uani 1 1 d . . . C4 C 0.4276(4) -0.0009(3) 0.0297(3) 0.0468(10) Uani 1 1 d . . . C5 C 0.5366(4) -0.0259(4) -0.0141(3) 0.0620(13) Uani 1 1 d . . . H5 H 0.6074 0.0125 -0.0068 0.074 Uiso 1 1 calc R . . C6 C 0.5403(4) -0.1043(4) -0.0662(3) 0.0633(14) Uani 1 1 d . . . H6 H 0.6125 -0.1182 -0.0958 0.076 Uiso 1 1 calc R . . C7 C 0.4355(4) -0.1656(4) -0.0762(3) 0.0559(12) Uani 1 1 d . . . C8 C 0.4345(5) -0.2458(4) -0.1330(3) 0.0670(13) Uani 1 1 d . . . H8 H 0.5062 -0.2602 -0.1630 0.080 Uiso 1 1 calc R . . C9 C 0.3340(6) -0.3018(4) -0.1450(3) 0.0735(14) Uani 1 1 d . . . H9 H 0.3351 -0.3522 -0.1848 0.088 Uiso 1 1 calc R . . C10 C 0.2259(5) -0.2841(4) -0.0969(3) 0.0671(14) Uani 1 1 d . . . H10 H 0.1571 -0.3250 -0.1032 0.081 Uiso 1 1 calc R . . C11 C 0.2225(4) -0.2069(3) -0.0412(2) 0.0510(10) Uani 1 1 d . . . H11 H 0.1506 -0.1957 -0.0105 0.061 Uiso 1 1 calc R . . C12 C 0.3256(4) -0.1441(3) -0.0294(2) 0.0421(9) Uani 1 1 d . . . C13 C 0.1130(3) 0.0231(3) 0.0191(2) 0.0377(9) Uani 1 1 d . . . C14 C 0.1441(3) 0.1125(3) -0.0182(2) 0.0455(10) Uani 1 1 d . . . H14 H 0.2236 0.1376 -0.0108 0.055 Uiso 1 1 calc R . . C15 C 0.0591(4) 0.1658(3) -0.0665(3) 0.0506(11) Uani 1 1 d . . . H15 H 0.0811 0.2259 -0.0910 0.061 Uiso 1 1 calc R . . C16 C -0.0582(4) 0.1269(4) -0.0768(3) 0.0547(11) Uani 1 1 d . . . C17 C -0.0920(4) 0.0393(4) -0.0396(3) 0.0598(12) Uani 1 1 d . . . H17 H -0.1718 0.0147 -0.0467 0.072 Uiso 1 1 calc R . . C18 C -0.0075(4) -0.0121(3) 0.0083(3) 0.0490(11) Uani 1 1 d . . . H18 H -0.0311 -0.0712 0.0337 0.059 Uiso 1 1 calc R . . C19 C 0.3243(5) 0.0472(4) 0.2851(3) 0.0630(12) Uani 1 1 d . . . H19A H 0.3737 0.0981 0.2595 0.094 Uiso 1 1 calc R . . H19B H 0.3712 0.0156 0.3287 0.094 Uiso 1 1 calc R . . H19C H 0.2507 0.0761 0.3085 0.094 Uiso 1 1 calc R . . C20 C 0.2105(3) -0.1124(3) 0.2564(2) 0.0419(10) Uani 1 1 d . . . C21 C 0.1088(4) -0.0902(4) 0.3038(3) 0.0592(12) Uani 1 1 d . . . H21 H 0.0831 -0.0246 0.3079 0.071 Uiso 1 1 calc R . . C22 C 0.0415(5) -0.1641(5) 0.3465(3) 0.0774(17) Uani 1 1 d . . . H22 H -0.0296 -0.1471 0.3761 0.093 Uiso 1 1 calc R . . C23 C 0.0795(5) -0.2596(4) 0.3449(3) 0.0764(15) Uani 1 1 d . . . H23 H 0.0382 -0.3067 0.3771 0.092 Uiso 1 1 calc R . . C24 C 0.1808(5) -0.2884(4) 0.2950(3) 0.0640(13) Uani 1 1 d . . . C25 C 0.2192(7) -0.3882(5) 0.2901(5) 0.094(2) Uani 1 1 d . . . H25 H 0.1793 -0.4361 0.3222 0.112 Uiso 1 1 calc R . . C26 C 0.3137(8) -0.4144(5) 0.2390(5) 0.109(2) Uani 1 1 d . . . H26 H 0.3381 -0.4804 0.2361 0.131 Uiso 1 1 calc R . . C27 C 0.3744(6) -0.3443(5) 0.1912(5) 0.095(2) Uani 1 1 d . . . H27 H 0.4375 -0.3639 0.1549 0.114 Uiso 1 1 calc R . . C28 C 0.3430(5) -0.2470(4) 0.1965(3) 0.0609(12) Uani 1 1 d . . . H28 H 0.3864 -0.2008 0.1646 0.073 Uiso 1 1 calc R . . C29 C 0.2460(4) -0.2141(3) 0.2493(2) 0.0458(10) 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 Br1 0.0883(4) 0.0703(4) 0.1203(5) 0.0002(4) -0.0538(3) 0.0205(3) O1 0.0560(19) 0.068(2) 0.063(2) -0.0008(18) -0.0003(15) -0.0182(15) N1 0.0505(18) 0.045(2) 0.0329(18) -0.0047(17) -0.0023(14) 0.0073(15) C1 0.043(2) 0.049(3) 0.031(2) -0.0007(18) -0.0031(15) 0.0002(17) C2 0.044(2) 0.038(2) 0.034(2) 0.0009(17) 0.0041(15) -0.0017(16) C3 0.0377(19) 0.044(2) 0.034(2) 0.0049(18) -0.0008(16) 0.0038(17) C4 0.045(2) 0.054(3) 0.041(2) 0.006(2) -0.0001(18) 0.0018(18) C5 0.043(2) 0.080(4) 0.063(3) 0.024(3) 0.002(2) 0.006(2) C6 0.041(3) 0.093(4) 0.056(3) 0.017(3) 0.0120(19) 0.020(2) C7 0.064(3) 0.068(3) 0.036(2) 0.009(2) 0.0056(19) 0.030(2) C8 0.087(4) 0.068(3) 0.046(3) 0.002(3) 0.011(3) 0.031(3) C9 0.123(4) 0.054(3) 0.043(3) -0.006(3) 0.001(3) 0.029(3) C10 0.099(4) 0.052(3) 0.051(3) 0.003(3) -0.004(3) -0.003(3) C11 0.066(3) 0.046(3) 0.040(2) -0.001(2) 0.0045(18) 0.001(2) C12 0.052(2) 0.045(2) 0.030(2) 0.0097(18) -0.0008(17) 0.0087(18) C13 0.042(2) 0.044(2) 0.027(2) -0.0041(18) 0.0023(15) 0.0037(16) C14 0.042(2) 0.055(3) 0.040(2) 0.000(2) 0.0007(16) -0.0042(17) C15 0.060(3) 0.047(3) 0.045(2) 0.002(2) -0.0045(19) 0.0053(19) C16 0.051(3) 0.053(3) 0.059(3) -0.005(2) -0.014(2) 0.013(2) C17 0.041(2) 0.065(3) 0.074(3) -0.003(3) -0.011(2) -0.004(2) C18 0.043(2) 0.051(3) 0.053(3) 0.008(2) 0.0055(17) -0.0062(18) C19 0.088(3) 0.060(3) 0.041(3) 0.001(2) -0.013(2) -0.021(3) C20 0.047(2) 0.052(3) 0.027(2) -0.0027(18) -0.0038(16) -0.0035(17) C21 0.065(3) 0.064(3) 0.049(3) -0.011(2) 0.013(2) -0.011(2) C22 0.068(3) 0.113(5) 0.051(3) -0.025(3) 0.025(2) -0.026(3) C23 0.104(4) 0.074(4) 0.051(3) -0.003(3) 0.007(3) -0.036(3) C24 0.084(3) 0.062(4) 0.046(3) 0.001(2) -0.012(2) -0.018(3) C25 0.123(6) 0.052(4) 0.106(5) 0.018(3) -0.019(4) -0.016(3) C26 0.140(6) 0.064(4) 0.124(6) 0.001(4) -0.026(6) 0.021(5) C27 0.101(5) 0.076(5) 0.109(5) -0.012(4) -0.018(4) 0.025(4) C28 0.061(3) 0.060(3) 0.062(3) -0.003(2) -0.007(2) 0.013(2) C29 0.051(2) 0.051(3) 0.036(2) 0.003(2) -0.0101(16) -0.0008(19) _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 Br1 C16 1.892(4) . ? O1 C4 1.349(5) . ? O1 H4 0.8200 . ? N1 C1 1.467(5) . ? N1 C2 1.482(5) . ? N1 H1N 0.89(4) . ? C1 C20 1.521(6) . ? C1 C19 1.525(6) . ? C1 H1 0.9800 . ? C2 C13 1.514(5) . ? C2 C3 1.527(5) . ? C2 H2 0.9800 . ? C3 C4 1.381(5) . ? C3 C12 1.427(5) . ? C4 C5 1.408(6) . ? C5 C6 1.346(7) . ? C5 H5 0.9300 . ? C6 C7 1.409(7) . ? C6 H6 0.9300 . ? C7 C8 1.410(7) . ? C7 C12 1.431(6) . ? C8 C9 1.334(7) . ? C8 H8 0.9300 . ? C9 C10 1.415(7) . ? C9 H9 0.9300 . ? C10 C11 1.369(6) . ? C10 H10 0.9300 . ? C11 C12 1.410(6) . ? C11 H11 0.9300 . ? C13 C14 1.386(5) . ? C13 C18 1.393(5) . ? C14 C15 1.396(6) . ? C14 H14 0.9300 . ? C15 C16 1.380(6) . ? C15 H15 0.9300 . ? C16 C17 1.372(7) . ? C17 C18 1.376(6) . ? C17 H17 0.9300 . ? C18 H18 0.9300 . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? C20 C21 1.365(5) . ? C20 C29 1.430(6) . ? C21 C22 1.409(7) . ? C21 H21 0.9300 . ? C22 C23 1.352(8) . ? C22 H22 0.9300 . ? C23 C24 1.406(8) . ? C23 H23 0.9300 . ? C24 C25 1.411(8) . ? C24 C29 1.425(6) . ? C25 C26 1.352(10) . ? C25 H25 0.9300 . ? C26 C27 1.380(10) . ? C26 H26 0.9300 . ? C27 C28 1.359(8) . ? C27 H27 0.9300 . ? C28 C29 1.414(6) . ? C28 H28 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C4 O1 H4 109.5 . . ? C1 N1 C2 116.3(3) . . ? C1 N1 H1N 113(3) . . ? C2 N1 H1N 108(3) . . ? N1 C1 C20 115.8(3) . . ? N1 C1 C19 107.2(3) . . ? C20 C1 C19 111.7(3) . . ? N1 C1 H1 107.3 . . ? C20 C1 H1 107.3 . . ? C19 C1 H1 107.3 . . ? N1 C2 C13 108.6(3) . . ? N1 C2 C3 111.7(3) . . ? C13 C2 C3 112.2(3) . . ? N1 C2 H2 108.0 . . ? C13 C2 H2 108.0 . . ? C3 C2 H2 108.0 . . ? C4 C3 C12 118.7(4) . . ? C4 C3 C2 121.4(3) . . ? C12 C3 C2 119.9(3) . . ? O1 C4 C3 124.5(4) . . ? O1 C4 C5 114.6(4) . . ? C3 C4 C5 120.9(4) . . ? C6 C5 C4 121.3(5) . . ? C6 C5 H5 119.4 . . ? C4 C5 H5 119.4 . . ? C5 C6 C7 120.5(4) . . ? C5 C6 H6 119.7 . . ? C7 C6 H6 119.7 . . ? C6 C7 C8 122.0(4) . . ? C6 C7 C12 119.1(4) . . ? C8 C7 C12 118.9(5) . . ? C9 C8 C7 122.2(5) . . ? C9 C8 H8 118.9 . . ? C7 C8 H8 118.9 . . ? C8 C9 C10 119.7(5) . . ? C8 C9 H9 120.2 . . ? C10 C9 H9 120.2 . . ? C11 C10 C9 120.1(5) . . ? C11 C10 H10 119.9 . . ? C9 C10 H10 119.9 . . ? C10 C11 C12 121.5(4) . . ? C10 C11 H11 119.3 . . ? C12 C11 H11 119.3 . . ? C11 C12 C3 123.0(4) . . ? C11 C12 C7 117.5(4) . . ? C3 C12 C7 119.4(4) . . ? C14 C13 C18 118.0(4) . . ? C14 C13 C2 121.6(3) . . ? C18 C13 C2 120.4(4) . . ? C13 C14 C15 121.8(4) . . ? C13 C14 H14 119.1 . . ? C15 C14 H14 119.1 . . ? C16 C15 C14 118.1(4) . . ? C16 C15 H15 121.0 . . ? C14 C15 H15 121.0 . . ? C17 C16 C15 121.4(4) . . ? C17 C16 Br1 119.4(3) . . ? C15 C16 Br1 119.2(4) . . ? C16 C17 C18 119.9(4) . . ? C16 C17 H17 120.1 . . ? C18 C17 H17 120.1 . . ? C17 C18 C13 120.9(4) . . ? C17 C18 H18 119.5 . . ? C13 C18 H18 119.5 . . ? C1 C19 H19A 109.5 . . ? C1 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C1 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C21 C20 C29 118.0(4) . . ? C21 C20 C1 119.9(4) . . ? C29 C20 C1 121.9(3) . . ? C20 C21 C22 121.7(5) . . ? C20 C21 H21 119.1 . . ? C22 C21 H21 119.1 . . ? C23 C22 C21 120.7(5) . . ? C23 C22 H22 119.7 . . ? C21 C22 H22 119.7 . . ? C22 C23 C24 120.6(5) . . ? C22 C23 H23 119.7 . . ? C24 C23 H23 119.7 . . ? C23 C24 C25 121.5(5) . . ? C23 C24 C29 118.6(5) . . ? C25 C24 C29 119.9(5) . . ? C26 C25 C24 120.3(6) . . ? C26 C25 H25 119.9 . . ? C24 C25 H25 119.9 . . ? C25 C26 C27 120.8(7) . . ? C25 C26 H26 119.6 . . ? C27 C26 H26 119.6 . . ? C28 C27 C26 120.6(7) . . ? C28 C27 H27 119.7 . . ? C26 C27 H27 119.7 . . ? C27 C28 C29 121.7(6) . . ? C27 C28 H28 119.2 . . ? C29 C28 H28 119.2 . . ? C28 C29 C24 116.7(4) . . ? C28 C29 C20 123.1(4) . . ? C24 C29 C20 120.2(4) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1 H4 N1 0.82 1.93 2.611(4) 139.3 . O1 H4 Br1 0.82 2.99 3.425(4) 115.3 3 _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.985 _refine_diff_density_max 0.292 _refine_diff_density_min -0.519 _refine_diff_density_rms 0.094 data_f1 _database_code_depnum_ccdc_archive 'CCDC 822821' _publ_section_title_footnote ? _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C26 H25 N O2' _chemical_formula_sum 'C26 H25 N O2' _chemical_formula_weight 383.47 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M P212121 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' _cell_length_a 15.510(3) _cell_length_b 15.661(3) _cell_length_c 17.891(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 4345.5(15) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3366 _cell_measurement_theta_min 2.17 _cell_measurement_theta_max 18.65 _exptl_crystal_description block' _exptl_crystal_colour colourless _exptl_crystal_size_max 0.52 _exptl_crystal_size_mid 0.34 _exptl_crystal_size_min 0.23 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.172 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1632 _exptl_absorpt_coefficient_mu 0.073 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9628 _exptl_absorpt_correction_T_max 0.9833 _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 SMART APEX' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 30166 _diffrn_reflns_av_R_equivalents 0.0438 _diffrn_reflns_av_sigmaI/netI 0.0701 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 1.73 _diffrn_reflns_theta_max 29.02 _reflns_number_total 10679 _reflns_number_gt 4659 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART 5.6 (Bruker)' _computing_cell_refinement 'SAINT 5.0 (Bruker)' _computing_data_reduction 'SAINT 5.0 (Bruker)' _computing_structure_solution 'SIR97 (Altomare et al., 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'DIAMOND 2.1e (1998-2001 Crystal Impact GbR)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0418P)^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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.4(12) _refine_ls_number_reflns 10679 _refine_ls_number_parameters 531 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1532 _refine_ls_R_factor_gt 0.0499 _refine_ls_wR_factor_ref 0.1114 _refine_ls_wR_factor_gt 0.0849 _refine_ls_goodness_of_fit_ref 0.931 _refine_ls_restrained_S_all 0.931 _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 O1A O 0.33109(10) -0.09902(9) 0.98566(11) 0.0783(5) Uani 1 1 d . . . H4A H 0.3715 -0.1271 1.0020 0.117 Uiso 1 1 calc R . . O2A O 0.63708(12) -0.51820(13) 0.81330(12) 0.1016(6) Uani 1 1 d . . . N1A N 0.43126(11) -0.22862(12) 0.99792(11) 0.0632(6) Uani 1 1 d . . . H1NA H 0.4617(15) -0.2506(14) 1.0316(13) 0.076 Uiso 1 1 d . . . C1A C 0.48524(14) -0.21680(15) 0.93064(14) 0.0669(7) Uani 1 1 d . . . H1A H 0.4480 -0.1924 0.8919 0.080 Uiso 1 1 calc R . . C2A C 0.35537(13) -0.28544(14) 0.98657(12) 0.0580(6) Uani 1 1 d . . . H2A H 0.3739 -0.3344 0.9565 0.070 Uiso 1 1 calc R . . C3A C 0.28530(13) -0.23825(14) 0.94340(12) 0.0533(6) Uani 1 1 d . . . C4A C 0.27798(14) -0.15071(15) 0.94479(13) 0.0595(6) Uani 1 1 d . . . C5A C 0.21270(15) -0.10767(15) 0.90431(13) 0.0653(6) Uani 1 1 d . . . H5A H 0.2094 -0.0484 0.9059 0.078 Uiso 1 1 calc R . . C6A C 0.15542(16) -0.15250(18) 0.86349(14) 0.0701(7) Uani 1 1 d . . . H6A H 0.1135 -0.1237 0.8361 0.084 Uiso 1 1 calc R . . C7A C 0.15813(15) -0.24303(17) 0.86167(13) 0.0643(6) Uani 1 1 d . . . C8A C 0.09618(17) -0.2906(2) 0.82133(14) 0.0860(8) Uani 1 1 d . . . H8A H 0.0538 -0.2620 0.7944 0.103 Uiso 1 1 calc R . . C9A C 0.09758(19) -0.3769(2) 0.82124(17) 0.0983(10) Uani 1 1 d . . . H9A H 0.0565 -0.4073 0.7943 0.118 Uiso 1 1 calc R . . C10A C 0.16033(18) -0.41979(17) 0.86144(16) 0.0840(8) Uani 1 1 d . . . H10A H 0.1607 -0.4792 0.8618 0.101 Uiso 1 1 calc R . . C11A C 0.22145(15) -0.37624(16) 0.90039(13) 0.0673(7) Uani 1 1 d . . . H11A H 0.2630 -0.4066 0.9268 0.081 Uiso 1 1 calc R . . C12A C 0.22341(13) -0.28589(15) 0.90174(12) 0.0543(6) Uani 1 1 d . . . C13A C 0.32339(14) -0.31859(16) 1.06114(13) 0.0622(6) Uani 1 1 d . . . C14A C 0.33870(16) -0.40207(17) 1.08214(16) 0.0798(8) Uani 1 1 d . . . H14A H 0.3698 -0.4378 1.0505 0.096 Uiso 1 1 calc R . . C15A C 0.3087(2) -0.4331(2) 1.1488(2) 0.1032(11) Uani 1 1 d . . . H15A H 0.3195 -0.4896 1.1618 0.124 Uiso 1 1 calc R . . C16A C 0.2634(2) -0.3823(3) 1.19617(19) 0.1091(12) Uani 1 1 d . . . H16A H 0.2430 -0.4040 1.2412 0.131 Uiso 1 1 calc R . . C17A C 0.24800(17) -0.2980(2) 1.17696(17) 0.0976(10) Uani 1 1 d . . . H17A H 0.2179 -0.2625 1.2094 0.117 Uiso 1 1 calc R . . C18A C 0.27762(15) -0.26667(18) 1.10915(15) 0.0753(7) Uani 1 1 d . . . H18A H 0.2666 -0.2103 1.0960 0.090 Uiso 1 1 calc R . . C19A C 0.55367(15) -0.15016(16) 0.94837(17) 0.0949(9) Uani 1 1 d . . . H19A H 0.5265 -0.0997 0.9678 0.142 Uiso 1 1 calc R . . H19B H 0.5847 -0.1361 0.9036 0.142 Uiso 1 1 calc R . . H19C H 0.5929 -0.1726 0.9849 0.142 Uiso 1 1 calc R . . C20A C 0.52345(14) -0.29775(16) 0.89881(14) 0.0604(6) Uani 1 1 d . . . C21A C 0.57453(15) -0.35120(17) 0.94094(15) 0.0750(7) Uani 1 1 d . . . H21A H 0.5844 -0.3381 0.9909 0.090 Uiso 1 1 calc R . . C22A C 0.61120(16) -0.42331(18) 0.91116(17) 0.0789(8) Uani 1 1 d . . . H22A H 0.6453 -0.4581 0.9411 0.095 Uiso 1 1 calc R . . C23A C 0.59807(17) -0.44460(19) 0.83762(17) 0.0760(8) Uani 1 1 d . . . C24A C 0.5474(2) -0.3924(2) 0.79467(16) 0.0995(10) Uani 1 1 d . . . H24A H 0.5374 -0.4054 0.7447 0.119 Uiso 1 1 calc R . . C25A C 0.51113(18) -0.3203(2) 0.82590(16) 0.0903(9) Uani 1 1 d . . . H25A H 0.4768 -0.2856 0.7960 0.108 Uiso 1 1 calc R . . C26A C 0.6291(3) -0.5402(2) 0.7370(2) 0.1577(17) Uani 1 1 d . . . H26A H 0.6595 -0.5926 0.7276 0.237 Uiso 1 1 calc R . . H26B H 0.6532 -0.4956 0.7067 0.237 Uiso 1 1 calc R . . H26C H 0.5693 -0.5475 0.7247 0.237 Uiso 1 1 calc R . . O1B O 0.19484(13) 0.09389(11) 0.99022(13) 0.1004(6) Uani 1 1 d . . . H4B H 0.1498 0.1195 0.9989 0.151 Uiso 1 1 calc R . . O2B O -0.08386(13) 0.50854(15) 0.77440(12) 0.1040(6) Uani 1 1 d . . . N1B N 0.08312(13) 0.21396(14) 0.97703(11) 0.0758(6) Uani 1 1 d . . . H1NB H 0.0422(16) 0.2378(16) 1.0050(14) 0.091 Uiso 1 1 d . . . C1B C 0.04491(17) 0.2022(2) 0.90157(15) 0.0868(8) Uani 1 1 d . . . H1B H 0.0913 0.1829 0.8684 0.104 Uiso 1 1 calc R . . C2B C 0.15534(14) 0.27686(15) 0.97976(12) 0.0624(6) Uani 1 1 d . . . H2B H 0.1413 0.3245 0.9464 0.075 Uiso 1 1 calc R . . C3B C 0.23851(14) 0.23537(15) 0.95233(12) 0.0587(6) Uani 1 1 d . . . C4B C 0.25291(17) 0.14848(17) 0.95874(14) 0.0720(7) Uani 1 1 d . . . C5B C 0.32975(19) 0.11074(18) 0.93430(15) 0.0818(8) Uani 1 1 d . . . H5B H 0.3378 0.0522 0.9394 0.098 Uiso 1 1 calc R . . C6B C 0.39210(17) 0.15928(18) 0.90331(15) 0.0759(8) Uani 1 1 d . . . H6B H 0.4427 0.1335 0.8869 0.091 Uiso 1 1 calc R . . C7B C 0.38207(15) 0.24818(17) 0.89530(13) 0.0627(7) Uani 1 1 d . . . C8B C 0.44834(15) 0.2989(2) 0.86455(14) 0.0784(8) Uani 1 1 d . . . H8B H 0.4982 0.2731 0.8466 0.094 Uiso 1 1 calc R . . C9B C 0.44001(19) 0.3845(2) 0.86089(16) 0.0926(9) Uani 1 1 d . . . H9B H 0.4843 0.4173 0.8410 0.111 Uiso 1 1 calc R . . C10B C 0.36551(19) 0.42370(18) 0.88674(15) 0.0860(8) Uani 1 1 d . . . H10B H 0.3606 0.4828 0.8840 0.103 Uiso 1 1 calc R . . C11B C 0.29934(16) 0.37700(16) 0.91617(13) 0.0686(7) Uani 1 1 d . . . H11B H 0.2501 0.4047 0.9333 0.082 Uiso 1 1 calc R . . C12B C 0.30481(14) 0.28696(15) 0.92097(12) 0.0559(6) Uani 1 1 d . . . C13B C 0.16258(14) 0.31112(17) 1.05886(14) 0.0659(7) Uani 1 1 d . . . C14B C 0.13028(16) 0.39101(19) 1.07510(16) 0.0807(8) Uani 1 1 d . . . H14B H 0.1051 0.4232 1.0373 0.097 Uiso 1 1 calc R . . C15B C 0.1346(2) 0.4239(2) 1.1463(2) 0.1021(10) Uani 1 1 d . . . H15B H 0.1134 0.4783 1.1562 0.122 Uiso 1 1 calc R . . C16B C 0.1696(2) 0.3773(3) 1.2018(2) 0.1123(12) Uani 1 1 d . . . H16B H 0.1717 0.3994 1.2500 0.135 Uiso 1 1 calc R . . C17B C 0.20258(19) 0.2968(3) 1.18749(17) 0.1055(10) Uani 1 1 d . . . H17B H 0.2273 0.2650 1.2258 0.127 Uiso 1 1 calc R . . C18B C 0.19839(17) 0.2641(2) 1.11552(16) 0.0871(8) Uani 1 1 d . . . H18B H 0.2200 0.2098 1.1057 0.104 Uiso 1 1 calc R . . C19B C -0.0210(2) 0.1289(2) 0.90713(18) 0.1222(12) Uani 1 1 d . . . H19D H 0.0063 0.0795 0.9281 0.183 Uiso 1 1 calc R . . H19E H -0.0424 0.1155 0.8582 0.183 Uiso 1 1 calc R . . H19F H -0.0681 0.1462 0.9385 0.183 Uiso 1 1 calc R . . C20B C 0.00872(16) 0.2829(2) 0.86841(15) 0.0778(8) Uani 1 1 d . . . C21B C -0.06634(19) 0.3210(3) 0.89489(16) 0.1064(11) Uani 1 1 d . . . H21B H -0.0962 0.2947 0.9337 0.128 Uiso 1 1 calc R . . C22B C -0.09809(19) 0.3957(3) 0.86618(19) 0.1077(11) Uani 1 1 d . . . H22B H -0.1481 0.4196 0.8859 0.129 Uiso 1 1 calc R . . C23B C -0.05632(18) 0.4350(2) 0.80866(17) 0.0830(8) Uani 1 1 d . . . C24B C 0.01802(18) 0.3995(2) 0.78134(15) 0.0852(9) Uani 1 1 d . . . H24B H 0.0473 0.4263 0.7425 0.102 Uiso 1 1 calc R . . C25B C 0.04953(16) 0.3255(2) 0.81035(16) 0.0825(8) Uani 1 1 d . . . H25B H 0.1000 0.3027 0.7906 0.099 Uiso 1 1 calc R . . C26B C -0.1513(3) 0.5544(3) 0.8069(3) 0.182(2) Uani 1 1 d . . . H26D H -0.1638 0.6038 0.7770 0.273 Uiso 1 1 calc R . . H26E H -0.1348 0.5722 0.8563 0.273 Uiso 1 1 calc R . . H26F H -0.2016 0.5189 0.8099 0.273 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 O1A 0.0684(12) 0.0634(11) 0.1031(14) -0.0057(10) -0.0192(10) -0.0040(9) O2A 0.1019(14) 0.0979(15) 0.1051(17) -0.0086(13) 0.0363(13) 0.0034(12) N1A 0.0444(12) 0.0805(15) 0.0647(13) 0.0066(11) -0.0104(10) -0.0059(10) C1A 0.0495(14) 0.0769(17) 0.0744(17) 0.0137(14) -0.0044(13) -0.0017(13) C2A 0.0426(13) 0.0663(16) 0.0653(15) -0.0011(12) -0.0076(12) 0.0026(12) C3A 0.0440(14) 0.0606(16) 0.0553(14) 0.0043(12) -0.0029(11) 0.0020(11) C4A 0.0507(15) 0.0672(17) 0.0606(15) 0.0032(13) 0.0002(12) -0.0011(13) C5A 0.0602(16) 0.0647(16) 0.0710(16) 0.0127(14) -0.0021(14) 0.0070(13) C6A 0.0584(16) 0.089(2) 0.0624(16) 0.0239(15) -0.0092(14) 0.0084(15) C7A 0.0552(15) 0.0802(19) 0.0577(15) 0.0114(14) -0.0103(13) -0.0052(14) C8A 0.0751(19) 0.104(2) 0.0788(19) 0.0102(17) -0.0313(16) -0.0040(18) C9A 0.092(2) 0.097(2) 0.106(2) -0.001(2) -0.041(2) -0.0205(19) C10A 0.082(2) 0.0770(19) 0.092(2) -0.0053(16) -0.0244(18) -0.0073(16) C11A 0.0620(16) 0.0731(18) 0.0666(16) -0.0040(13) -0.0085(13) -0.0004(13) C12A 0.0464(13) 0.0657(17) 0.0510(13) 0.0029(12) 0.0005(11) -0.0023(12) C13A 0.0434(14) 0.0802(18) 0.0631(16) 0.0125(14) -0.0120(12) -0.0060(12) C14A 0.0712(18) 0.085(2) 0.083(2) 0.0219(16) -0.0138(15) -0.0044(15) C15A 0.093(2) 0.117(3) 0.100(3) 0.044(2) -0.031(2) -0.029(2) C16A 0.079(2) 0.175(4) 0.073(2) 0.041(3) -0.0165(19) -0.039(2) C17A 0.0664(19) 0.155(3) 0.072(2) 0.007(2) -0.0028(15) -0.005(2) C18A 0.0573(16) 0.104(2) 0.0649(17) 0.0103(16) -0.0043(13) 0.0048(15) C19A 0.0661(18) 0.084(2) 0.134(3) 0.0032(18) 0.0086(17) -0.0140(15) C20A 0.0425(13) 0.0761(17) 0.0626(16) 0.0131(14) -0.0010(12) -0.0058(13) C21A 0.0676(17) 0.0851(19) 0.0724(18) -0.0025(15) -0.0126(14) 0.0098(15) C22A 0.0664(18) 0.088(2) 0.082(2) 0.0064(17) -0.0078(15) 0.0057(15) C23A 0.0643(18) 0.085(2) 0.079(2) 0.0009(17) 0.0242(16) -0.0051(15) C24A 0.118(3) 0.121(3) 0.0595(19) 0.0021(19) 0.0059(18) 0.021(2) C25A 0.093(2) 0.112(2) 0.066(2) 0.0144(17) -0.0018(16) 0.0168(18) C26A 0.218(5) 0.155(4) 0.101(3) -0.022(2) 0.066(3) 0.034(3) O1B 0.1037(14) 0.0729(13) 0.1245(16) 0.0105(12) 0.0305(14) -0.0164(11) O2B 0.0782(14) 0.1268(18) 0.1069(16) -0.0136(15) -0.0059(13) -0.0093(14) N1B 0.0590(14) 0.1041(17) 0.0643(14) -0.0143(12) 0.0053(11) -0.0225(13) C1B 0.0692(18) 0.121(3) 0.0702(18) -0.0253(18) 0.0075(15) -0.0265(18) C2B 0.0514(14) 0.0766(17) 0.0593(15) -0.0057(12) -0.0015(12) -0.0055(13) C3B 0.0530(15) 0.0679(17) 0.0552(14) -0.0009(12) 0.0038(12) 0.0001(12) C4B 0.0744(19) 0.0716(19) 0.0700(17) 0.0000(14) 0.0080(14) -0.0071(15) C5B 0.087(2) 0.0661(17) 0.092(2) -0.0080(15) 0.0082(17) 0.0105(17) C6B 0.0676(18) 0.083(2) 0.0767(19) -0.0201(15) 0.0012(14) 0.0149(16) C7B 0.0508(15) 0.0776(19) 0.0596(15) -0.0118(14) 0.0028(12) -0.0029(13) C8B 0.0546(16) 0.108(2) 0.0730(17) -0.0178(17) 0.0096(14) -0.0044(17) C9B 0.080(2) 0.102(3) 0.096(2) -0.0034(19) 0.0213(17) -0.0269(18) C10B 0.084(2) 0.079(2) 0.095(2) 0.0057(16) 0.0142(17) -0.0104(17) C11B 0.0620(17) 0.0711(18) 0.0727(18) 0.0051(14) 0.0065(14) 0.0011(13) C12B 0.0506(14) 0.0681(17) 0.0489(13) -0.0016(11) 0.0000(11) -0.0018(12) C13B 0.0440(14) 0.0898(19) 0.0639(16) -0.0103(15) 0.0042(13) -0.0062(13) C14B 0.0689(18) 0.094(2) 0.079(2) -0.0175(17) 0.0053(14) -0.0112(15) C15B 0.102(2) 0.109(3) 0.095(3) -0.030(2) 0.004(2) -0.0230(19) C16B 0.101(3) 0.154(4) 0.082(3) -0.038(3) 0.006(2) -0.040(2) C17B 0.085(2) 0.161(4) 0.071(2) 0.000(2) -0.0131(17) -0.007(2) C18B 0.0714(18) 0.117(2) 0.073(2) -0.0033(18) -0.0061(15) 0.0066(16) C19B 0.114(2) 0.144(3) 0.109(2) -0.023(2) -0.005(2) -0.063(2) C20B 0.0490(16) 0.127(3) 0.0577(16) -0.0183(18) -0.0005(14) -0.0208(17) C21B 0.068(2) 0.181(4) 0.071(2) 0.011(2) 0.0136(17) -0.010(2) C22B 0.066(2) 0.175(4) 0.082(2) 0.003(2) 0.0110(18) 0.005(2) C23B 0.0515(18) 0.123(3) 0.074(2) -0.0209(19) -0.0070(17) -0.0195(18) C24B 0.0611(19) 0.120(3) 0.075(2) -0.0146(18) 0.0105(16) -0.0248(18) C25B 0.0548(17) 0.120(3) 0.0729(19) -0.0294(18) 0.0107(15) -0.0246(17) C26B 0.130(3) 0.225(5) 0.191(4) 0.018(4) 0.039(3) 0.072(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 O1A C4A 1.367(3) . ? O2A C23A 1.373(3) . ? O2A C26A 1.414(4) . ? N1A C1A 1.478(3) . ? N1A C2A 1.489(3) . ? C1A C20A 1.511(3) . ? C1A C19A 1.522(3) . ? C2A C13A 1.515(3) . ? C2A C3A 1.524(3) . ? C3A C4A 1.376(3) . ? C3A C12A 1.426(3) . ? C4A C5A 1.416(3) . ? C5A C6A 1.347(3) . ? C6A C7A 1.419(3) . ? C7A C12A 1.411(3) . ? C7A C8A 1.414(3) . ? C8A C9A 1.351(4) . ? C9A C10A 1.384(3) . ? C10A C11A 1.360(3) . ? C11A C12A 1.415(3) . ? C13A C18A 1.379(3) . ? C13A C14A 1.381(3) . ? C14A C15A 1.369(4) . ? C15A C16A 1.358(4) . ? C16A C17A 1.386(4) . ? C17A C18A 1.387(4) . ? C20A C25A 1.365(3) . ? C20A C21A 1.377(3) . ? C21A C22A 1.372(3) . ? C22A C23A 1.372(4) . ? C23A C24A 1.371(4) . ? C24A C25A 1.379(4) . ? O1B C4B 1.364(3) . ? O2B C23B 1.373(3) . ? O2B C26B 1.396(4) . ? N1B C1B 1.486(3) . ? N1B C2B 1.492(3) . ? C1B C20B 1.504(4) . ? C1B C19B 1.541(4) . ? C2B C13B 1.518(3) . ? C2B C3B 1.525(3) . ? C3B C4B 1.384(3) . ? C3B C12B 1.423(3) . ? C4B C5B 1.400(3) . ? C5B C6B 1.349(4) . ? C6B C7B 1.408(3) . ? C7B C8B 1.411(3) . ? C7B C12B 1.420(3) . ? C8B C9B 1.348(4) . ? C9B C10B 1.388(4) . ? C10B C11B 1.366(3) . ? C11B C12B 1.415(3) . ? C13B C18B 1.371(3) . ? C13B C14B 1.379(3) . ? C14B C15B 1.376(4) . ? C15B C16B 1.346(4) . ? C16B C17B 1.384(4) . ? C17B C18B 1.388(4) . ? C20B C25B 1.387(3) . ? C20B C21B 1.392(4) . ? C21B C22B 1.369(4) . ? C22B C23B 1.363(4) . ? C23B C24B 1.370(4) . ? C24B C25B 1.361(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 C23A O2A C26A 118.2(3) . . ? C1A N1A C2A 114.30(18) . . ? N1A C1A C20A 115.09(19) . . ? N1A C1A C19A 108.1(2) . . ? C20A C1A C19A 112.36(19) . . ? N1A C2A C13A 110.08(17) . . ? N1A C2A C3A 110.06(17) . . ? C13A C2A C3A 112.27(18) . . ? C4A C3A C12A 118.4(2) . . ? C4A C3A C2A 122.2(2) . . ? C12A C3A C2A 119.41(19) . . ? O1A C4A C3A 123.4(2) . . ? O1A C4A C5A 115.0(2) . . ? C3A C4A C5A 121.6(2) . . ? C6A C5A C4A 120.1(2) . . ? C5A C6A C7A 120.9(2) . . ? C12A C7A C8A 119.8(2) . . ? C12A C7A C6A 119.0(2) . . ? C8A C7A C6A 121.2(2) . . ? C9A C8A C7A 121.1(3) . . ? C8A C9A C10A 119.8(3) . . ? C11A C10A C9A 120.8(3) . . ? C10A C11A C12A 121.7(2) . . ? C7A C12A C11A 116.8(2) . . ? C7A C12A C3A 120.0(2) . . ? C11A C12A C3A 123.1(2) . . ? C18A C13A C14A 118.5(2) . . ? C18A C13A C2A 121.0(2) . . ? C14A C13A C2A 120.5(2) . . ? C15A C14A C13A 121.0(3) . . ? C16A C15A C14A 120.8(3) . . ? C15A C16A C17A 119.5(3) . . ? C16A C17A C18A 119.8(3) . . ? C13A C18A C17A 120.4(3) . . ? C25A C20A C21A 116.5(3) . . ? C25A C20A C1A 121.5(2) . . ? C21A C20A C1A 122.0(2) . . ? C22A C21A C20A 121.8(3) . . ? C21A C22A C23A 120.7(3) . . ? C24A C23A C22A 118.5(3) . . ? C24A C23A O2A 125.2(3) . . ? C22A C23A O2A 116.3(3) . . ? C23A C24A C25A 119.7(3) . . ? C20A C25A C24A 122.8(3) . . ? C23B O2B C26B 118.6(3) . . ? C1B N1B C2B 114.25(19) . . ? N1B C1B C20B 113.8(2) . . ? N1B C1B C19B 107.3(2) . . ? C20B C1B C19B 113.8(2) . . ? N1B C2B C13B 108.63(18) . . ? N1B C2B C3B 110.06(19) . . ? C13B C2B C3B 112.84(19) . . ? C4B C3B C12B 118.3(2) . . ? C4B C3B C2B 121.9(2) . . ? C12B C3B C2B 119.7(2) . . ? O1B C4B C3B 123.0(2) . . ? O1B C4B C5B 115.2(3) . . ? C3B C4B C5B 121.8(2) . . ? C6B C5B C4B 120.0(3) . . ? C5B C6B C7B 121.3(3) . . ? C6B C7B C8B 121.1(3) . . ? C6B C7B C12B 118.9(2) . . ? C8B C7B C12B 120.0(2) . . ? C9B C8B C7B 120.6(3) . . ? C8B C9B C10B 120.2(3) . . ? C11B C10B C9B 121.1(3) . . ? C10B C11B C12B 120.8(2) . . ? C11B C12B C7B 117.2(2) . . ? C11B C12B C3B 123.1(2) . . ? C7B C12B C3B 119.6(2) . . ? C18B C13B C14B 118.6(2) . . ? C18B C13B C2B 122.0(3) . . ? C14B C13B C2B 119.4(2) . . ? C15B C14B C13B 121.1(3) . . ? C16B C15B C14B 120.0(3) . . ? C15B C16B C17B 120.4(3) . . ? C16B C17B C18B 119.4(3) . . ? C13B C18B C17B 120.4(3) . . ? C25B C20B C21B 115.5(3) . . ? C25B C20B C1B 121.9(3) . . ? C21B C20B C1B 122.6(3) . . ? C22B C21B C20B 122.7(3) . . ? C23B C22B C21B 119.9(3) . . ? C22B C23B C24B 119.1(3) . . ? C22B C23B O2B 124.6(3) . . ? C24B C23B O2B 116.3(3) . . ? C25B C24B C23B 120.8(3) . . ? C24B C25B C20B 122.1(3) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1A H4A N1A 0.82 1.84 2.565(2) 146.6 . O1B H4B N1B 0.82 1.85 2.568(3) 146.0 . C5A H5A O1B 0.93 2.70 3.522(3) 147.7 . C5B H5B O1A 0.93 2.51 3.411(3) 163.1 . C9A H9A O2B 0.93 2.57 3.441(3) 156.1 1_545 C22A H22A O1B 0.93 2.57 3.454(3) 158.4 4_547 C9B H9B O2A 0.93 2.62 3.520(3) 162.4 1_565 C26B H26F O2A 0.96 2.57 3.476(5) 157.5 1_465 _diffrn_measured_fraction_theta_max 0.946 _diffrn_reflns_theta_full 29.02 _diffrn_measured_fraction_theta_full 0.946 _refine_diff_density_max 0.106 _refine_diff_density_min -0.093 _refine_diff_density_rms 0.022