# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2012 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_rc55 _database_code_depnum_ccdc_archive 'CCDC 753483' _audit_creation_method SHELXLTL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H17 Cl O' _chemical_formula_weight 296.78 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.508(2) _cell_length_b 10.191(3) _cell_length_c 12.222(4) _cell_angle_alpha 91.608(6) _cell_angle_beta 103.611(5) _cell_angle_gamma 101.668(5) _cell_volume 769.1(4) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 2489 _cell_measurement_theta_min 2.57 _cell_measurement_theta_max 25.94 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.281 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 312 _exptl_absorpt_coefficient_mu 0.244 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9043 _exptl_absorpt_correction_T_max 0.9807 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Apex CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8622 _diffrn_reflns_av_R_equivalents 0.0249 _diffrn_reflns_av_sigmaI/netI 0.0315 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.72 _diffrn_reflns_theta_max 27.00 _reflns_number_total 3318 _reflns_number_gt 2666 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0519P)^2^+0.1415P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3318 _refine_ls_number_parameters 258 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0525 _refine_ls_R_factor_gt 0.0408 _refine_ls_wR_factor_ref 0.1065 _refine_ls_wR_factor_gt 0.0977 _refine_ls_goodness_of_fit_ref 1.017 _refine_ls_restrained_S_all 1.017 _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 1.06723(7) 0.25087(5) 0.44928(4) 0.05298(17) Uani 1 1 d . . . O1 O 0.0688(2) -0.07038(12) 0.84631(11) 0.0543(4) Uani 1 1 d . . . C1 C 0.4535(2) 0.18210(14) 0.75736(12) 0.0281(3) Uani 1 1 d . . . C2 C 0.6050(2) 0.19535(15) 0.67853(12) 0.0299(3) Uani 1 1 d . . . C3 C 0.7623(3) 0.32232(18) 0.54192(13) 0.0372(4) Uani 1 1 d . . . C4 C 0.5472(2) 0.28060(14) 0.86655(12) 0.0271(3) Uani 1 1 d . . . C5 C 0.2196(3) 0.02627(16) 0.85793(14) 0.0369(4) Uani 1 1 d . . . C6 C 0.5441(2) 0.42414(14) 0.83339(12) 0.0273(3) Uani 1 1 d . . . C7 C 0.8741(3) 0.11903(18) 0.60021(14) 0.0397(4) Uani 1 1 d . . . C8 C 0.8880(3) 0.22900(18) 0.53694(13) 0.0377(4) Uani 1 1 d . . . C9 C 0.4040(2) 0.24915(16) 0.94818(13) 0.0313(3) Uani 1 1 d . . . C10 C 0.2570(3) 0.13644(16) 0.94464(14) 0.0343(4) Uani 1 1 d . . . C11 C 0.6200(3) 0.30387(16) 0.61116(13) 0.0330(3) Uani 1 1 d . . . C12 C 0.7340(3) 0.10308(17) 0.67099(14) 0.0367(4) Uani 1 1 d . . . C13 C 0.7308(3) 0.51911(15) 0.83329(13) 0.0354(4) Uani 1 1 d . . . C14 C 0.3821(3) 0.03730(15) 0.78665(15) 0.0354(4) Uani 1 1 d . . . C15 C 0.3447(3) 0.46019(16) 0.79523(13) 0.0342(4) Uani 1 1 d . . . C16 C 0.7744(3) 0.26413(19) 0.92889(15) 0.0371(4) Uani 1 1 d . . . C17 C 0.7190(4) 0.64380(17) 0.79308(15) 0.0462(5) Uani 1 1 d . . . C18 C 0.5211(4) 0.67697(17) 0.75373(15) 0.0511(5) Uani 1 1 d . . . C19 C 0.3323(4) 0.58536(18) 0.75576(15) 0.0463(4) Uani 1 1 d . . . H1 H 0.325(2) 0.2106(14) 0.7162(12) 0.023(4) Uiso 1 1 d . . . H2 H 0.530(3) 0.3675(16) 0.6129(13) 0.033(4) Uiso 1 1 d . . . H3 H 0.429(3) 0.3200(17) 1.0082(15) 0.040(5) Uiso 1 1 d . . . H4 H 0.316(3) -0.0242(18) 0.7171(16) 0.048(5) Uiso 1 1 d . . . H5 H 0.770(3) 0.1703(19) 0.9492(15) 0.043(5) Uiso 1 1 d . . . H6 H 0.505(3) 0.0052(18) 0.8327(15) 0.044(5) Uiso 1 1 d . . . H7 H 0.772(3) 0.3964(18) 0.4969(15) 0.044(5) Uiso 1 1 d . . . H8 H 0.727(3) 0.0269(19) 0.7149(15) 0.047(5) Uiso 1 1 d . . . H9 H 0.875(3) 0.4966(17) 0.8581(15) 0.043(5) Uiso 1 1 d . . . H10 H 0.849(3) 0.7051(18) 0.7950(15) 0.045(5) Uiso 1 1 d . . . H11 H 0.214(3) 0.3945(18) 0.7907(14) 0.043(5) Uiso 1 1 d . . . H12 H 0.832(3) 0.3269(19) 0.9984(17) 0.050(5) Uiso 1 1 d . . . H13 H 0.873(3) 0.2815(18) 0.8793(15) 0.045(5) Uiso 1 1 d . . . H14 H 0.172(3) 0.1248(18) 0.9987(15) 0.045(5) Uiso 1 1 d . . . H15 H 0.505(3) 0.763(2) 0.7241(18) 0.068(6) Uiso 1 1 d . . . H16 H 0.955(3) 0.0563(19) 0.5941(16) 0.052(5) Uiso 1 1 d . . . H17 H 0.189(3) 0.6064(19) 0.7301(17) 0.055(6) 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 Cl1 0.0494(3) 0.0752(4) 0.0439(3) 0.0076(2) 0.0242(2) 0.0201(2) O1 0.0568(8) 0.0397(7) 0.0564(8) 0.0102(6) 0.0155(6) -0.0148(6) C1 0.0272(7) 0.0246(7) 0.0309(8) 0.0026(6) 0.0052(6) 0.0043(6) C2 0.0311(7) 0.0285(8) 0.0280(7) -0.0011(6) 0.0048(6) 0.0051(6) C3 0.0439(9) 0.0418(10) 0.0279(8) 0.0056(7) 0.0114(7) 0.0105(8) C4 0.0261(7) 0.0267(7) 0.0275(7) 0.0026(6) 0.0070(6) 0.0034(6) C5 0.0375(9) 0.0304(8) 0.0394(9) 0.0132(7) 0.0063(7) 0.0015(7) C6 0.0335(8) 0.0244(7) 0.0251(7) 0.0007(6) 0.0119(6) 0.0030(6) C7 0.0408(9) 0.0421(10) 0.0398(9) -0.0017(8) 0.0109(7) 0.0166(8) C8 0.0362(8) 0.0490(10) 0.0284(8) -0.0022(7) 0.0104(7) 0.0080(7) C9 0.0343(8) 0.0314(8) 0.0294(8) 0.0054(7) 0.0101(6) 0.0070(6) C10 0.0335(8) 0.0362(9) 0.0366(9) 0.0127(7) 0.0139(7) 0.0078(7) C11 0.0379(8) 0.0341(8) 0.0290(8) 0.0023(6) 0.0082(7) 0.0121(7) C12 0.0418(9) 0.0319(9) 0.0382(9) 0.0037(7) 0.0107(7) 0.0108(7) C13 0.0415(9) 0.0296(8) 0.0340(8) -0.0038(6) 0.0166(7) -0.0028(7) C14 0.0410(9) 0.0244(8) 0.0389(9) 0.0037(7) 0.0086(7) 0.0042(7) C15 0.0381(9) 0.0326(8) 0.0345(8) 0.0044(7) 0.0119(7) 0.0097(7) C16 0.0298(8) 0.0410(10) 0.0380(9) 0.0065(8) 0.0037(7) 0.0072(7) C17 0.0679(13) 0.0285(9) 0.0403(10) -0.0027(7) 0.0268(9) -0.0088(9) C18 0.0969(17) 0.0248(9) 0.0383(10) 0.0057(7) 0.0281(10) 0.0146(10) C19 0.0672(13) 0.0415(10) 0.0388(10) 0.0087(8) 0.0173(9) 0.0256(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl1 C8 1.7478(16) . ? O1 C5 1.2202(19) . ? C1 C2 1.523(2) . ? C1 C14 1.534(2) . ? C1 C4 1.567(2) . ? C1 H1 0.974(15) . ? C2 C12 1.396(2) . ? C2 C11 1.399(2) . ? C3 C11 1.384(2) . ? C3 C8 1.383(2) . ? C3 H7 0.948(18) . ? C4 C9 1.517(2) . ? C4 C6 1.532(2) . ? C4 C16 1.540(2) . ? C5 C10 1.464(2) . ? C5 C14 1.510(2) . ? C6 C13 1.392(2) . ? C6 C15 1.398(2) . ? C7 C8 1.379(2) . ? C7 C12 1.388(2) . ? C7 H16 0.917(19) . ? C9 C10 1.330(2) . ? C9 H3 0.975(18) . ? C10 H14 0.951(18) . ? C11 H2 0.958(16) . ? C12 H8 0.956(18) . ? C13 C17 1.385(2) . ? C13 H9 0.989(18) . ? C14 H4 0.99(2) . ? C14 H6 0.984(18) . ? C15 C19 1.387(2) . ? C15 H11 0.959(18) . ? C16 H5 0.991(18) . ? C16 H12 1.00(2) . ? C16 H13 0.975(19) . ? C17 C18 1.378(3) . ? C17 H10 0.940(19) . ? C18 C19 1.391(3) . ? C18 H15 0.97(2) . ? C19 H17 0.98(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C14 113.33(12) . . ? C2 C1 C4 112.54(12) . . ? C14 C1 C4 111.25(13) . . ? C2 C1 H1 105.7(8) . . ? C14 C1 H1 107.6(8) . . ? C4 C1 H1 105.9(9) . . ? C12 C2 C11 117.64(14) . . ? C12 C2 C1 122.45(14) . . ? C11 C2 C1 119.91(13) . . ? C11 C3 C8 119.11(15) . . ? C11 C3 H7 121.0(11) . . ? C8 C3 H7 119.9(11) . . ? C9 C4 C6 107.75(11) . . ? C9 C4 C16 106.62(12) . . ? C6 C4 C16 112.71(12) . . ? C9 C4 C1 109.75(12) . . ? C6 C4 C1 108.47(11) . . ? C16 C4 C1 111.45(12) . . ? O1 C5 C10 121.64(16) . . ? O1 C5 C14 122.17(16) . . ? C10 C5 C14 116.16(13) . . ? C13 C6 C15 117.92(14) . . ? C13 C6 C4 123.07(14) . . ? C15 C6 C4 118.91(13) . . ? C8 C7 C12 119.38(15) . . ? C8 C7 H16 120.0(12) . . ? C12 C7 H16 120.6(12) . . ? C7 C8 C3 120.96(15) . . ? C7 C8 Cl1 119.55(13) . . ? C3 C8 Cl1 119.48(13) . . ? C10 C9 C4 125.95(15) . . ? C10 C9 H3 120.1(10) . . ? C4 C9 H3 114.0(10) . . ? C9 C10 C5 121.51(15) . . ? C9 C10 H14 120.8(11) . . ? C5 C10 H14 117.7(11) . . ? C3 C11 C2 121.58(15) . . ? C3 C11 H2 118.9(10) . . ? C2 C11 H2 119.6(10) . . ? C7 C12 C2 121.30(16) . . ? C7 C12 H8 118.4(11) . . ? C2 C12 H8 120.2(11) . . ? C17 C13 C6 121.02(17) . . ? C17 C13 H9 118.7(10) . . ? C6 C13 H9 120.2(10) . . ? C5 C14 C1 111.91(13) . . ? C5 C14 H4 108.3(11) . . ? C1 C14 H4 111.1(10) . . ? C5 C14 H6 105.0(10) . . ? C1 C14 H6 111.0(10) . . ? H4 C14 H6 109.3(15) . . ? C19 C15 C6 121.19(16) . . ? C19 C15 H11 119.5(10) . . ? C6 C15 H11 119.2(10) . . ? C4 C16 H5 110.3(10) . . ? C4 C16 H12 110.7(11) . . ? H5 C16 H12 109.7(15) . . ? C4 C16 H13 109.9(10) . . ? H5 C16 H13 106.5(14) . . ? H12 C16 H13 109.6(15) . . ? C18 C17 C13 120.39(17) . . ? C18 C17 H10 121.4(11) . . ? C13 C17 H10 118.2(11) . . ? C17 C18 C19 119.78(17) . . ? C17 C18 H15 123.1(13) . . ? C19 C18 H15 117.1(13) . . ? C18 C19 C15 119.66(19) . . ? C18 C19 H17 121.9(12) . . ? C15 C19 H17 118.4(12) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C14 C1 C2 C12 -24.7(2) . . . . ? C4 C1 C2 C12 102.60(16) . . . . ? C14 C1 C2 C11 155.95(14) . . . . ? C4 C1 C2 C11 -76.73(17) . . . . ? C2 C1 C4 C9 -172.27(12) . . . . ? C14 C1 C4 C9 -43.85(16) . . . . ? C2 C1 C4 C6 70.25(15) . . . . ? C14 C1 C4 C6 -161.33(12) . . . . ? C2 C1 C4 C16 -54.40(16) . . . . ? C14 C1 C4 C16 74.02(16) . . . . ? C9 C4 C6 C13 132.73(14) . . . . ? C16 C4 C6 C13 15.4(2) . . . . ? C1 C4 C6 C13 -108.52(15) . . . . ? C9 C4 C6 C15 -51.00(17) . . . . ? C16 C4 C6 C15 -168.36(14) . . . . ? C1 C4 C6 C15 67.74(16) . . . . ? C12 C7 C8 C3 -0.9(3) . . . . ? C12 C7 C8 Cl1 179.04(13) . . . . ? C11 C3 C8 C7 -0.4(3) . . . . ? C11 C3 C8 Cl1 179.69(12) . . . . ? C6 C4 C9 C10 134.60(16) . . . . ? C16 C4 C9 C10 -104.16(18) . . . . ? C1 C4 C9 C10 16.7(2) . . . . ? C4 C9 C10 C5 0.7(2) . . . . ? O1 C5 C10 C9 -171.42(15) . . . . ? C14 C5 C10 C9 10.5(2) . . . . ? C8 C3 C11 C2 1.9(2) . . . . ? C12 C2 C11 C3 -2.0(2) . . . . ? C1 C2 C11 C3 177.32(14) . . . . ? C8 C7 C12 C2 0.7(3) . . . . ? C11 C2 C12 C7 0.7(2) . . . . ? C1 C2 C12 C7 -178.62(15) . . . . ? C15 C6 C13 C17 -2.1(2) . . . . ? C4 C6 C13 C17 174.16(14) . . . . ? O1 C5 C14 C1 142.92(16) . . . . ? C10 C5 C14 C1 -39.0(2) . . . . ? C2 C1 C14 C5 -175.86(13) . . . . ? C4 C1 C14 C5 56.14(17) . . . . ? C13 C6 C15 C19 1.6(2) . . . . ? C4 C6 C15 C19 -174.85(14) . . . . ? C6 C13 C17 C18 0.9(2) . . . . ? C13 C17 C18 C19 0.8(3) . . . . ? C17 C18 C19 C15 -1.3(3) . . . . ? C6 C15 C19 C18 0.1(3) . . . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.239 _refine_diff_density_min -0.227 _refine_diff_density_rms 0.040 data_rc56 _database_code_depnum_ccdc_archive 'CCDC 753484' _audit_creation_method SHELXLTL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H15 Br O' _chemical_formula_weight 279.17 _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1) _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 6.240(3) _cell_length_b 7.706(3) _cell_length_c 12.861(5) _cell_angle_alpha 90.00 _cell_angle_beta 98.015(7) _cell_angle_gamma 90.00 _cell_volume 612.4(4) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 2200 _cell_measurement_theta_min 3.09 _cell_measurement_theta_max 22.35 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.514 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 284 _exptl_absorpt_coefficient_mu 3.332 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.4347 _exptl_absorpt_correction_T_max 0.8251 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Apex CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6842 _diffrn_reflns_av_R_equivalents 0.0374 _diffrn_reflns_av_sigmaI/netI 0.0573 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.60 _diffrn_reflns_theta_max 27.00 _reflns_number_total 2647 _reflns_number_gt 2393 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0143P)^2^+0.0850P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _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 0.034(11) _refine_ls_number_reflns 2647 _refine_ls_number_parameters 205 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0382 _refine_ls_R_factor_gt 0.0327 _refine_ls_wR_factor_ref 0.0688 _refine_ls_wR_factor_gt 0.0638 _refine_ls_goodness_of_fit_ref 1.012 _refine_ls_restrained_S_all 1.011 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _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 0.17465(5) 0.46703(6) 0.29663(2) 0.03829(12) Uani 1 1 d . . . O1 O 0.0938(4) 0.3667(3) 1.0519(2) 0.0378(6) Uani 1 1 d . . . C1 C 0.2442(5) 0.4627(7) 0.4452(2) 0.0287(6) Uani 1 1 d . . . C2 C 0.0978(6) 0.3893(5) 0.5050(3) 0.0334(8) Uani 1 1 d . . . C3 C 0.1521(6) 0.3827(5) 0.6135(3) 0.0309(8) Uani 1 1 d . . . C4 C 0.3503(5) 0.4449(5) 0.6633(2) 0.0249(7) Uani 1 1 d . . . C5 C 0.4921(6) 0.5169(4) 0.6002(3) 0.0317(9) Uani 1 1 d . . . C6 C 0.4394(6) 0.5263(4) 0.4925(3) 0.0331(9) Uani 1 1 d . . . C7 C 0.3983(5) 0.4362(4) 0.7830(2) 0.0238(8) Uani 1 1 d . . . C8 C 0.2778(6) 0.5867(5) 0.8308(3) 0.0253(8) Uani 1 1 d . . . C9 C 0.2743(6) 0.5605(5) 0.9483(3) 0.0283(8) Uani 1 1 d . . . C10 C 0.1823(6) 0.3880(5) 0.9735(3) 0.0262(8) Uani 1 1 d . . . C11 C 0.2128(6) 0.2440(5) 0.9026(3) 0.0276(7) Uani 1 1 d . . . C12 C 0.3148(6) 0.2648(5) 0.8197(3) 0.0255(8) Uani 1 1 d . . . C13 C 0.6438(5) 0.4408(7) 0.8222(3) 0.0318(9) Uani 1 1 d . . . C14 C 0.3614(8) 0.7655(6) 0.8115(4) 0.0352(10) Uani 1 1 d . . . H2 H -0.031(6) 0.345(5) 0.470(3) 0.029(10) Uiso 1 1 d . . . H3 H 0.059(6) 0.323(5) 0.664(3) 0.049(12) Uiso 1 1 d . . . H5 H 0.628(6) 0.561(5) 0.638(3) 0.038(10) Uiso 1 1 d . . . H6 H 0.527(6) 0.572(5) 0.445(3) 0.041(11) Uiso 1 1 d . . . H8 H 0.122(5) 0.585(4) 0.802(2) 0.022(9) Uiso 1 1 d . . . H9A H 0.190(5) 0.644(5) 0.980(3) 0.021(9) Uiso 1 1 d . . . H9B H 0.424(5) 0.561(4) 0.983(2) 0.015(8) Uiso 1 1 d . . . H11 H 0.163(5) 0.133(4) 0.929(2) 0.022(9) Uiso 1 1 d . . . H12 H 0.334(5) 0.177(4) 0.784(3) 0.006(9) Uiso 1 1 d . . . H13A H 0.673(5) 0.423(4) 0.905(2) 0.025(9) Uiso 1 1 d . . . H13B H 0.733(7) 0.344(6) 0.795(3) 0.043(13) Uiso 1 1 d . . . H13C H 0.697(5) 0.541(5) 0.804(2) 0.004(9) Uiso 1 1 d . . . H14A H 0.532(7) 0.786(5) 0.855(3) 0.055(12) Uiso 1 1 d . . . H14B H 0.259(6) 0.856(5) 0.846(3) 0.044(11) Uiso 1 1 d . . . H14C H 0.365(5) 0.787(4) 0.762(3) 0.009(10) Uiso 1 1 d . . . _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 0.0443(2) 0.0447(2) 0.02575(16) 0.0023(2) 0.00437(12) 0.0096(2) O1 0.0416(15) 0.0440(15) 0.0291(14) -0.0003(11) 0.0096(12) -0.0037(12) C1 0.0338(16) 0.0267(14) 0.0261(14) -0.002(3) 0.0053(12) 0.005(2) C2 0.0260(19) 0.038(2) 0.034(2) -0.0017(15) -0.0007(16) -0.0047(15) C3 0.0292(19) 0.037(2) 0.0272(19) 0.0036(15) 0.0049(15) -0.0058(16) C4 0.0267(15) 0.021(2) 0.0268(15) -0.0013(16) 0.0023(12) -0.0038(15) C5 0.0281(17) 0.031(2) 0.0364(19) -0.0015(14) 0.0042(15) -0.0071(14) C6 0.0339(19) 0.035(2) 0.033(2) 0.0043(14) 0.0124(16) -0.0018(15) C7 0.0228(14) 0.023(2) 0.0265(15) -0.0013(14) 0.0048(12) 0.0003(13) C8 0.0244(18) 0.0199(17) 0.031(2) 0.0005(16) 0.0033(15) -0.0006(14) C9 0.026(2) 0.033(2) 0.026(2) -0.0083(16) 0.0036(16) -0.0033(17) C10 0.024(2) 0.0312(19) 0.0225(19) 0.0002(15) 0.0001(15) 0.0042(15) C11 0.0306(19) 0.0237(18) 0.0270(19) 0.0009(15) -0.0006(15) -0.0024(14) C12 0.031(2) 0.0183(19) 0.028(2) -0.0028(17) 0.0042(15) 0.0040(16) C13 0.0253(17) 0.035(3) 0.0347(19) -0.003(2) 0.0034(14) 0.0029(17) C14 0.046(3) 0.029(2) 0.032(3) 0.002(2) 0.010(2) -0.0028(18) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; _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 C1 1.900(3) . ? O1 C10 1.226(5) . ? C1 C6 1.374(5) . ? C1 C2 1.393(5) . ? C2 C3 1.390(5) . ? C2 H2 0.93(4) . ? C3 C4 1.396(5) . ? C3 H3 1.04(4) . ? C4 C5 1.396(4) . ? C4 C7 1.528(4) . ? C5 C6 1.381(5) . ? C5 H5 0.98(4) . ? C6 H6 0.94(4) . ? C7 C12 1.519(5) . ? C7 C13 1.545(5) . ? C7 C8 1.555(5) . ? C8 C14 1.506(6) . ? C8 C9 1.527(5) . ? C8 H8 0.99(3) . ? C9 C10 1.502(5) . ? C9 H9A 0.96(3) . ? C9 H9B 0.98(3) . ? C10 C11 1.465(5) . ? C11 C12 1.326(5) . ? C11 H11 0.99(3) . ? C12 H12 0.84(4) . ? C13 H13A 1.06(3) . ? C13 H13B 1.02(4) . ? C13 H13C 0.89(3) . ? C14 H14A 1.14(4) . ? C14 H14B 1.08(4) . ? C14 H14C 0.66(3) . ? _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 C6 C1 C2 120.7(3) . . ? C6 C1 Br1 120.2(3) . . ? C2 C1 Br1 119.1(3) . . ? C3 C2 C1 118.8(3) . . ? C3 C2 H2 123(2) . . ? C1 C2 H2 118(2) . . ? C2 C3 C4 121.6(3) . . ? C2 C3 H3 124(2) . . ? C4 C3 H3 114(2) . . ? C5 C4 C3 117.6(3) . . ? C5 C4 C7 123.5(3) . . ? C3 C4 C7 118.9(3) . . ? C6 C5 C4 121.5(3) . . ? C6 C5 H5 123(2) . . ? C4 C5 H5 115(2) . . ? C1 C6 C5 119.8(3) . . ? C1 C6 H6 114(2) . . ? C5 C6 H6 126(2) . . ? C12 C7 C4 108.9(3) . . ? C12 C7 C13 106.6(3) . . ? C4 C7 C13 112.0(3) . . ? C12 C7 C8 108.7(3) . . ? C4 C7 C8 109.2(3) . . ? C13 C7 C8 111.4(3) . . ? C14 C8 C9 109.8(3) . . ? C14 C8 C7 114.8(3) . . ? C9 C8 C7 111.5(3) . . ? C14 C8 H8 107(2) . . ? C9 C8 H8 102.7(18) . . ? C7 C8 H8 110.0(19) . . ? C10 C9 C8 113.0(3) . . ? C10 C9 H9A 105(2) . . ? C8 C9 H9A 115(2) . . ? C10 C9 H9B 105.8(18) . . ? C8 C9 H9B 108.2(18) . . ? H9A C9 H9B 110(3) . . ? O1 C10 C11 121.6(4) . . ? O1 C10 C9 121.7(3) . . ? C11 C10 C9 116.6(3) . . ? C12 C11 C10 121.9(3) . . ? C12 C11 H11 126.4(18) . . ? C10 C11 H11 111.4(18) . . ? C11 C12 C7 125.4(3) . . ? C11 C12 H12 118(2) . . ? C7 C12 H12 117(2) . . ? C7 C13 H13A 110.2(17) . . ? C7 C13 H13B 116(2) . . ? H13A C13 H13B 103(3) . . ? C7 C13 H13C 109(2) . . ? H13A C13 H13C 112(3) . . ? H13B C13 H13C 108(3) . . ? C8 C14 H14A 111(2) . . ? C8 C14 H14B 107(2) . . ? H14A C14 H14B 106(3) . . ? C8 C14 H14C 117(3) . . ? H14A C14 H14C 106(4) . . ? H14B C14 H14C 109(4) . . ? _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 0.5(7) . . . . ? Br1 C1 C2 C3 178.4(3) . . . . ? C1 C2 C3 C4 -1.1(6) . . . . ? C2 C3 C4 C5 0.9(6) . . . . ? C2 C3 C4 C7 179.1(3) . . . . ? C3 C4 C5 C6 -0.1(5) . . . . ? C7 C4 C5 C6 -178.2(3) . . . . ? C2 C1 C6 C5 0.3(7) . . . . ? Br1 C1 C6 C5 -177.6(3) . . . . ? C4 C5 C6 C1 -0.5(6) . . . . ? C5 C4 C7 C12 -141.8(4) . . . . ? C3 C4 C7 C12 40.1(4) . . . . ? C5 C4 C7 C13 -24.2(5) . . . . ? C3 C4 C7 C13 157.8(4) . . . . ? C5 C4 C7 C8 99.7(4) . . . . ? C3 C4 C7 C8 -78.3(4) . . . . ? C12 C7 C8 C14 173.3(4) . . . . ? C4 C7 C8 C14 -68.0(4) . . . . ? C13 C7 C8 C14 56.1(4) . . . . ? C12 C7 C8 C9 47.7(4) . . . . ? C4 C7 C8 C9 166.4(3) . . . . ? C13 C7 C8 C9 -69.5(4) . . . . ? C14 C8 C9 C10 177.1(3) . . . . ? C7 C8 C9 C10 -54.5(4) . . . . ? C8 C9 C10 O1 -152.7(4) . . . . ? C8 C9 C10 C11 30.2(5) . . . . ? O1 C10 C11 C12 -177.7(3) . . . . ? C9 C10 C11 C12 -0.5(5) . . . . ? C10 C11 C12 C7 -4.3(6) . . . . ? C4 C7 C12 C11 -138.7(4) . . . . ? C13 C7 C12 C11 100.3(4) . . . . ? C8 C7 C12 C11 -19.9(4) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.408 _refine_diff_density_min -0.279 _refine_diff_density_rms 0.062 data_rc67 _database_code_depnum_ccdc_archive 'CCDC 869713' #TrackingRef '- Compound 23 (rc67).cif' _audit_creation_method SHELXLTL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H16 O' _chemical_formula_weight 200.27 _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) _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 6.2640(8) _cell_length_b 7.7902(10) _cell_length_c 22.956(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1120.2(2) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 3833 _cell_measurement_theta_min 2.76 _cell_measurement_theta_max 26.99 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.187 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 432 _exptl_absorpt_coefficient_mu 0.073 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9821 _exptl_absorpt_correction_T_max 0.9964 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Apex CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12563 _diffrn_reflns_av_R_equivalents 0.0259 _diffrn_reflns_av_sigmaI/netI 0.0191 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 1.77 _diffrn_reflns_theta_max 26.99 _reflns_number_total 2425 _reflns_number_gt 2250 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0545P)^2^+0.1001P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 1.5(15) _refine_ls_number_reflns 2425 _refine_ls_number_parameters 200 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0380 _refine_ls_R_factor_gt 0.0344 _refine_ls_wR_factor_ref 0.0916 _refine_ls_wR_factor_gt 0.0883 _refine_ls_goodness_of_fit_ref 1.017 _refine_ls_restrained_S_all 1.017 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _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 O1 O 0.93688(16) 0.37944(13) 0.22298(4) 0.0429(3) Uani 1 1 d . . . C1 C 0.54844(19) 0.44945(16) 0.37065(5) 0.0296(3) Uani 1 1 d . . . C2 C 0.6591(2) 0.28384(16) 0.35390(6) 0.0328(3) Uani 1 1 d . . . C3 C 0.7844(2) 0.26168(17) 0.30772(6) 0.0334(3) Uani 1 1 d . . . C4 C 0.8224(2) 0.40008(17) 0.26557(5) 0.0322(3) Uani 1 1 d . . . C5 C 0.7063(2) 0.56527(17) 0.27622(6) 0.0348(3) Uani 1 1 d . . . C6 C 0.6667(2) 0.60143(16) 0.34084(5) 0.0295(3) Uani 1 1 d . . . C7 C 0.3154(2) 0.4336(2) 0.34956(7) 0.0434(3) Uani 1 1 d . . . C8 C 0.5572(3) 0.77458(18) 0.34831(7) 0.0402(3) Uani 1 1 d . . . C9 C 0.5608(2) 0.47244(15) 0.43687(5) 0.0317(3) Uani 1 1 d . . . C10 C 0.7461(3) 0.42493(19) 0.46641(6) 0.0417(3) Uani 1 1 d . . . C11 C 0.7656(3) 0.4495(2) 0.52598(7) 0.0552(4) Uani 1 1 d . . . C12 C 0.6022(3) 0.5230(2) 0.55743(7) 0.0593(5) Uani 1 1 d . . . C13 C 0.4200(3) 0.5719(2) 0.52880(7) 0.0600(5) Uani 1 1 d . . . C14 C 0.3981(3) 0.5468(2) 0.46914(7) 0.0454(4) Uani 1 1 d . . . H2 H 0.632(3) 0.188(2) 0.3784(7) 0.042(4) Uiso 1 1 d . . . H3 H 0.845(2) 0.154(2) 0.2998(6) 0.036(4) Uiso 1 1 d . . . H5A H 0.790(3) 0.661(2) 0.2588(6) 0.048(4) Uiso 1 1 d . . . H5B H 0.567(3) 0.557(2) 0.2552(7) 0.048(4) Uiso 1 1 d . . . H6 H 0.807(2) 0.6120(17) 0.3590(5) 0.028(3) Uiso 1 1 d . . . H7A H 0.242(3) 0.341(2) 0.3675(8) 0.058(5) Uiso 1 1 d . . . H7B H 0.311(3) 0.410(2) 0.3078(7) 0.049(5) Uiso 1 1 d . . . H7C H 0.232(3) 0.539(2) 0.3583(7) 0.046(4) Uiso 1 1 d . . . H8A H 0.419(3) 0.777(2) 0.3274(7) 0.049(4) Uiso 1 1 d . . . H8B H 0.525(3) 0.800(2) 0.3885(7) 0.044(4) Uiso 1 1 d . . . H8C H 0.649(3) 0.867(2) 0.3310(7) 0.054(5) Uiso 1 1 d . . . H10 H 0.862(3) 0.377(2) 0.4461(7) 0.050(5) Uiso 1 1 d . . . H11 H 0.895(4) 0.414(3) 0.5442(9) 0.071(6) Uiso 1 1 d . . . H12 H 0.620(3) 0.540(2) 0.5976(8) 0.067(5) Uiso 1 1 d . . . H13 H 0.304(4) 0.631(3) 0.5483(9) 0.081(6) Uiso 1 1 d . . . H14 H 0.264(3) 0.577(2) 0.4504(7) 0.047(4) Uiso 1 1 d . . . _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 O1 0.0427(5) 0.0490(6) 0.0369(5) 0.0006(4) 0.0079(4) 0.0012(5) C1 0.0267(6) 0.0291(6) 0.0329(6) -0.0017(5) -0.0024(5) -0.0026(5) C2 0.0360(7) 0.0264(6) 0.0359(6) -0.0004(5) 0.0015(5) -0.0052(5) C3 0.0344(7) 0.0272(6) 0.0387(6) -0.0041(5) 0.0018(5) 0.0002(6) C4 0.0288(6) 0.0374(7) 0.0304(6) -0.0014(5) -0.0041(5) -0.0044(5) C5 0.0371(7) 0.0344(7) 0.0327(6) 0.0044(5) -0.0029(5) 0.0013(6) C6 0.0287(6) 0.0269(6) 0.0330(6) -0.0004(4) -0.0056(5) 0.0009(5) C7 0.0298(7) 0.0530(9) 0.0475(8) -0.0086(7) -0.0042(6) -0.0056(7) C8 0.0487(8) 0.0308(7) 0.0412(8) 0.0001(6) -0.0051(7) 0.0082(6) C9 0.0345(6) 0.0265(6) 0.0341(7) -0.0001(5) 0.0011(5) -0.0025(5) C10 0.0467(8) 0.0381(7) 0.0403(7) 0.0011(6) -0.0075(6) 0.0032(6) C11 0.0732(12) 0.0493(9) 0.0430(8) 0.0055(7) -0.0181(8) -0.0055(9) C12 0.0939(14) 0.0527(10) 0.0315(8) -0.0019(7) 0.0028(8) -0.0226(10) C13 0.0717(12) 0.0610(11) 0.0473(9) -0.0147(8) 0.0215(9) -0.0114(10) C14 0.0434(8) 0.0462(8) 0.0465(8) -0.0086(7) 0.0077(6) -0.0013(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. ; _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C4 1.2232(16) . ? C1 C2 1.5142(18) . ? C1 C9 1.5325(17) . ? C1 C7 1.5428(19) . ? C1 C6 1.5553(17) . ? C2 C3 1.3304(18) . ? C2 H2 0.950(16) . ? C3 C4 1.4681(18) . ? C3 H3 0.938(16) . ? C4 C5 1.4982(18) . ? C5 C6 1.5302(18) . ? C5 H5A 0.995(19) . ? C5 H5B 1.001(16) . ? C6 C8 1.5230(18) . ? C6 H6 0.979(14) . ? C7 H7A 0.950(19) . ? C7 H7B 0.976(16) . ? C7 H7C 0.992(17) . ? C8 H8A 0.989(18) . ? C8 H8B 0.965(16) . ? C8 H8C 1.002(19) . ? C9 C14 1.386(2) . ? C9 C10 1.395(2) . ? C10 C11 1.386(2) . ? C10 H10 0.944(18) . ? C11 C12 1.378(3) . ? C11 H11 0.95(2) . ? C12 C13 1.371(3) . ? C12 H12 0.939(18) . ? C13 C14 1.390(2) . ? C13 H13 0.97(2) . ? C14 H14 0.973(18) . ? _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C9 109.18(11) . . ? C2 C1 C7 106.57(11) . . ? C9 C1 C7 111.61(11) . . ? C2 C1 C6 108.59(10) . . ? C9 C1 C6 108.87(10) . . ? C7 C1 C6 111.94(11) . . ? C3 C2 C1 125.67(12) . . ? C3 C2 H2 118.5(10) . . ? C1 C2 H2 115.9(10) . . ? C2 C3 C4 121.70(12) . . ? C2 C3 H3 120.6(9) . . ? C4 C3 H3 117.6(9) . . ? O1 C4 C3 121.68(12) . . ? O1 C4 C5 121.87(12) . . ? C3 C4 C5 116.40(11) . . ? C4 C5 C6 113.26(11) . . ? C4 C5 H5A 108.9(10) . . ? C6 C5 H5A 109.6(9) . . ? C4 C5 H5B 106.9(10) . . ? C6 C5 H5B 109.7(9) . . ? H5A C5 H5B 108.4(14) . . ? C8 C6 C5 110.19(11) . . ? C8 C6 C1 114.21(11) . . ? C5 C6 C1 111.32(10) . . ? C8 C6 H6 106.5(8) . . ? C5 C6 H6 106.5(8) . . ? C1 C6 H6 107.8(8) . . ? C1 C7 H7A 112.7(12) . . ? C1 C7 H7B 110.4(11) . . ? H7A C7 H7B 105.5(14) . . ? C1 C7 H7C 111.5(10) . . ? H7A C7 H7C 106.6(15) . . ? H7B C7 H7C 110.0(13) . . ? C6 C8 H8A 110.9(10) . . ? C6 C8 H8B 112.8(10) . . ? H8A C8 H8B 106.0(14) . . ? C6 C8 H8C 109.4(10) . . ? H8A C8 H8C 107.1(14) . . ? H8B C8 H8C 110.6(14) . . ? C14 C9 C10 117.57(13) . . ? C14 C9 C1 122.81(12) . . ? C10 C9 C1 119.55(12) . . ? C11 C10 C9 121.09(16) . . ? C11 C10 H10 118.4(10) . . ? C9 C10 H10 120.5(10) . . ? C12 C11 C10 120.60(17) . . ? C12 C11 H11 121.4(13) . . ? C10 C11 H11 118.0(13) . . ? C13 C12 C11 118.88(15) . . ? C13 C12 H12 122.1(12) . . ? C11 C12 H12 119.1(12) . . ? C12 C13 C14 120.99(18) . . ? C12 C13 H13 122.2(13) . . ? C14 C13 H13 116.7(13) . . ? C9 C14 C13 120.86(16) . . ? C9 C14 H14 120.0(10) . . ? C13 C14 H14 119.1(10) . . ? _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C9 C1 C2 C3 -139.58(14) . . . . ? C7 C1 C2 C3 99.74(16) . . . . ? C6 C1 C2 C3 -21.01(17) . . . . ? C1 C2 C3 C4 -2.5(2) . . . . ? C2 C3 C4 O1 -179.68(13) . . . . ? C2 C3 C4 C5 -2.11(18) . . . . ? O1 C4 C5 C6 -151.47(12) . . . . ? C3 C4 C5 C6 30.96(16) . . . . ? C4 C5 C6 C8 177.51(12) . . . . ? C4 C5 C6 C1 -54.72(15) . . . . ? C2 C1 C6 C8 173.37(11) . . . . ? C9 C1 C6 C8 -67.87(13) . . . . ? C7 C1 C6 C8 55.99(15) . . . . ? C2 C1 C6 C5 47.80(13) . . . . ? C9 C1 C6 C5 166.57(11) . . . . ? C7 C1 C6 C5 -69.57(14) . . . . ? C2 C1 C9 C14 -144.95(13) . . . . ? C7 C1 C9 C14 -27.40(18) . . . . ? C6 C1 C9 C14 96.65(15) . . . . ? C2 C1 C9 C10 38.20(16) . . . . ? C7 C1 C9 C10 155.75(13) . . . . ? C6 C1 C9 C10 -80.19(14) . . . . ? C14 C9 C10 C11 0.7(2) . . . . ? C1 C9 C10 C11 177.74(13) . . . . ? C9 C10 C11 C12 -0.6(2) . . . . ? C10 C11 C12 C13 -0.1(3) . . . . ? C11 C12 C13 C14 0.6(3) . . . . ? C10 C9 C14 C13 -0.2(2) . . . . ? C1 C9 C14 C13 -177.15(14) . . . . ? C12 C13 C14 C9 -0.4(3) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 26.99 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.232 _refine_diff_density_min -0.157 _refine_diff_density_rms 0.030 data_rc57 _database_code_depnum_ccdc_archive 'CCDC 869714' #TrackingRef '- compound 39 (rc57).cif' _audit_creation_method SHELXLTL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H38 N2 O5 S' _chemical_formula_weight 466.62 _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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1) _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 5.5897(13) _cell_length_b 9.123(2) _cell_length_c 24.114(6) _cell_angle_alpha 90.00 _cell_angle_beta 94.260(4) _cell_angle_gamma 90.00 _cell_volume 1226.2(5) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 3359 _cell_measurement_theta_min 2.39 _cell_measurement_theta_max 27.25 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.29 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.264 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 504 _exptl_absorpt_coefficient_mu 0.169 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9527 _exptl_absorpt_correction_T_max 0.9900 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Apex CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10969 _diffrn_reflns_av_R_equivalents 0.0237 _diffrn_reflns_av_sigmaI/netI 0.0359 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -30 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_theta_min 0.85 _diffrn_reflns_theta_max 27.00 _reflns_number_total 4958 _reflns_number_gt 4520 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0695P)^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 0.01(7) _refine_ls_number_reflns 4958 _refine_ls_number_parameters 441 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0475 _refine_ls_R_factor_gt 0.0407 _refine_ls_wR_factor_ref 0.1149 _refine_ls_wR_factor_gt 0.0990 _refine_ls_goodness_of_fit_ref 1.081 _refine_ls_restrained_S_all 1.081 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _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 S1 S 0.51605(9) 0.26947(7) 0.90509(2) 0.02618(15) Uani 1 1 d . . . O1 O 0.6393(3) 0.5089(2) 0.98265(7) 0.0405(5) Uani 1 1 d . . . O2 O 0.2831(3) 0.3152(2) 0.91960(7) 0.0352(5) Uani 1 1 d . . . O3 O 0.5273(3) 0.1251(2) 0.88063(7) 0.0348(4) Uani 1 1 d . . . O4 O 1.0376(3) 0.6378(2) 0.70820(8) 0.0373(4) Uani 1 1 d . . . O5 O 0.7846(4) 0.8151(2) 0.72933(10) 0.0544(6) Uani 1 1 d . . . N1 N 0.9772(4) 0.5170(3) 1.06381(9) 0.0301(5) Uani 1 1 d . . . N2 N 0.7225(3) 0.2717(2) 0.95464(7) 0.0246(4) Uani 1 1 d . . . C1 C 0.9789(5) 0.4681(3) 1.12339(10) 0.0302(5) Uani 1 1 d . . . C2 C 0.8573(5) 0.3217(3) 1.11923(11) 0.0343(6) Uani 1 1 d . . . C3 C 0.9587(6) 0.2522(3) 1.06857(11) 0.0391(6) Uani 1 1 d . . . C4 C 0.9730(4) 0.3819(3) 1.02772(10) 0.0289(5) Uani 1 1 d . . . C5 C 0.7558(4) 0.3947(3) 0.98538(9) 0.0263(5) Uani 1 1 d . . . C6 C 0.6120(4) 0.3953(3) 0.85463(9) 0.0252(5) Uani 1 1 d . . . C7 C 0.4948(5) 0.5254(3) 0.84386(12) 0.0386(6) Uani 1 1 d . . . C8 C 0.5754(5) 0.6214(3) 0.80503(12) 0.0408(7) Uani 1 1 d . . . C9 C 0.7736(4) 0.5853(3) 0.77636(10) 0.0263(5) Uani 1 1 d . . . C10 C 0.8896(5) 0.4545(3) 0.78756(12) 0.0402(7) Uani 1 1 d . . . C11 C 0.8093(5) 0.3597(4) 0.82667(13) 0.0437(7) Uani 1 1 d . . . C12 C 0.8608(4) 0.6935(3) 0.73585(10) 0.0304(6) Uani 1 1 d . . . C13 C 1.1497(5) 0.7352(3) 0.67011(12) 0.0342(6) Uani 1 1 d . . . C14 C 1.3087(5) 0.6443(3) 0.63640(11) 0.0327(6) Uani 1 1 d . . . C15 C 1.4427(5) 0.7367(3) 0.59653(11) 0.0323(6) Uani 1 1 d . . . C16 C 1.6025(5) 0.6480(3) 0.56072(11) 0.0316(5) Uani 1 1 d . . . C17 C 1.7383(5) 0.7401(3) 0.52090(11) 0.0322(6) Uani 1 1 d . . . C18 C 1.8950(5) 0.6506(3) 0.48469(11) 0.0318(5) Uani 1 1 d . . . C19 C 2.0342(5) 0.7416(3) 0.44511(11) 0.0321(6) Uani 1 1 d . . . C20 C 2.1885(5) 0.6509(3) 0.40889(11) 0.0330(6) Uani 1 1 d . . . C21 C 2.3323(5) 0.7400(3) 0.36961(11) 0.0320(6) Uani 1 1 d . . . C22 C 2.4821(5) 0.6453(3) 0.33380(11) 0.0336(6) Uani 1 1 d . . . C23 C 2.6270(6) 0.7291(3) 0.29376(12) 0.0365(6) Uani 1 1 d . . . C24 C 2.7629(7) 0.6291(4) 0.25703(15) 0.0487(8) Uani 1 1 d . . . H1N H 1.110(7) 0.568(4) 1.0605(17) 0.072(12) Uiso 1 1 d . . . H2N H 0.847(7) 0.561(4) 1.0556(16) 0.061(11) Uiso 1 1 d . . . H1A H 0.907(5) 0.540(3) 1.1442(12) 0.034(7) Uiso 1 1 d . . . H1B H 1.147(6) 0.461(3) 1.1391(12) 0.043(8) Uiso 1 1 d . . . H2A H 0.681(5) 0.331(3) 1.1132(12) 0.040(8) Uiso 1 1 d . . . H2B H 0.881(5) 0.263(4) 1.1556(13) 0.045(8) Uiso 1 1 d . . . H3A H 1.109(6) 0.223(4) 1.0786(14) 0.056(10) Uiso 1 1 d . . . H3B H 0.858(6) 0.183(4) 1.0522(15) 0.056(10) Uiso 1 1 d . . . H4 H 1.121(4) 0.380(3) 1.0088(10) 0.021(6) Uiso 1 1 d . . . H7 H 0.365(7) 0.543(4) 0.8594(15) 0.064(11) Uiso 1 1 d . . . H8 H 0.487(5) 0.711(4) 0.7956(13) 0.051(9) Uiso 1 1 d . . . H10 H 1.020(6) 0.429(4) 0.7656(14) 0.051(9) Uiso 1 1 d . . . H11 H 0.886(5) 0.273(5) 0.8327(13) 0.052(9) Uiso 1 1 d . . . H13A H 1.031(5) 0.776(4) 0.6484(12) 0.042(8) Uiso 1 1 d . . . H13B H 1.249(5) 0.802(3) 0.6903(11) 0.033(7) Uiso 1 1 d . . . H14A H 1.416(5) 0.592(3) 0.6612(13) 0.040(8) Uiso 1 1 d . . . H14B H 1.224(6) 0.579(4) 0.6190(13) 0.043(9) Uiso 1 1 d . . . H15A H 1.335(5) 0.787(4) 0.5735(12) 0.041(8) Uiso 1 1 d . . . H15B H 1.545(5) 0.804(4) 0.6185(13) 0.051(9) Uiso 1 1 d . . . H16A H 1.718(5) 0.590(3) 0.5864(12) 0.034(7) Uiso 1 1 d . . . H16B H 1.511(5) 0.576(4) 0.5388(12) 0.040(8) Uiso 1 1 d . . . H17A H 1.844(6) 0.811(4) 0.5434(14) 0.053(9) Uiso 1 1 d . . . H17B H 1.608(5) 0.799(4) 0.4954(13) 0.055(9) Uiso 1 1 d . . . H18A H 1.790(6) 0.586(4) 0.4589(14) 0.051(9) Uiso 1 1 d . . . H18B H 2.015(5) 0.590(3) 0.5098(12) 0.033(7) Uiso 1 1 d . . . H19A H 2.142(5) 0.811(4) 0.4670(13) 0.041(8) Uiso 1 1 d . . . H19B H 1.905(5) 0.806(4) 0.4184(12) 0.043(8) Uiso 1 1 d . . . H20A H 2.085(5) 0.587(3) 0.3825(12) 0.036(8) Uiso 1 1 d . . . H20B H 2.304(5) 0.591(3) 0.4341(13) 0.040(8) Uiso 1 1 d . . . H21A H 2.444(5) 0.810(4) 0.3902(12) 0.039(8) Uiso 1 1 d . . . H21B H 2.218(4) 0.802(3) 0.3442(11) 0.033(7) Uiso 1 1 d . . . H22A H 2.592(5) 0.584(3) 0.3574(13) 0.038(8) Uiso 1 1 d . . . H22B H 2.379(6) 0.587(4) 0.3116(14) 0.048(9) Uiso 1 1 d . . . H23A H 2.508(6) 0.790(4) 0.2696(13) 0.053(9) Uiso 1 1 d . . . H23B H 2.731(5) 0.777(4) 0.3132(13) 0.047(9) Uiso 1 1 d . . . H24A H 2.665(7) 0.567(4) 0.2395(15) 0.060(11) Uiso 1 1 d . . . H24B H 2.839(7) 0.676(5) 0.2321(18) 0.081(13) Uiso 1 1 d . . . H24C H 2.875(8) 0.569(5) 0.2812(18) 0.083(14) Uiso 1 1 d . . . _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 S1 0.0235(2) 0.0312(3) 0.0245(3) 0.0025(2) 0.00589(18) -0.0032(2) O1 0.0511(11) 0.0308(10) 0.0386(10) -0.0037(8) -0.0046(8) 0.0114(9) O2 0.0243(8) 0.0500(13) 0.0324(9) 0.0063(8) 0.0099(7) -0.0017(7) O3 0.0369(9) 0.0354(11) 0.0320(9) -0.0020(8) 0.0025(7) -0.0082(8) O4 0.0442(10) 0.0334(11) 0.0374(10) 0.0097(9) 0.0233(8) 0.0062(8) O5 0.0667(14) 0.0358(13) 0.0658(14) 0.0198(10) 0.0382(12) 0.0160(10) N1 0.0337(12) 0.0292(12) 0.0275(10) -0.0032(9) 0.0032(9) -0.0030(9) N2 0.0262(8) 0.0266(10) 0.0217(8) 0.0014(9) 0.0060(6) -0.0009(9) C1 0.0360(13) 0.0327(14) 0.0224(11) -0.0026(10) 0.0048(10) 0.0016(10) C2 0.0402(14) 0.0337(15) 0.0287(12) 0.0044(11) 0.0016(10) -0.0036(11) C3 0.0561(16) 0.0274(15) 0.0320(13) -0.0037(12) -0.0072(11) 0.0118(14) C4 0.0338(12) 0.0273(13) 0.0261(12) -0.0043(10) 0.0049(10) 0.0013(10) C5 0.0304(11) 0.0292(13) 0.0201(10) 0.0032(10) 0.0079(8) 0.0019(9) C6 0.0239(10) 0.0327(13) 0.0195(10) 0.0017(10) 0.0047(8) -0.0018(9) C7 0.0378(14) 0.0372(16) 0.0436(15) 0.0051(13) 0.0228(12) 0.0075(12) C8 0.0456(15) 0.0352(16) 0.0441(16) 0.0132(13) 0.0213(12) 0.0146(13) C9 0.0297(11) 0.0281(13) 0.0213(11) 0.0011(9) 0.0034(9) -0.0004(9) C10 0.0394(14) 0.0429(17) 0.0415(15) 0.0124(13) 0.0244(12) 0.0130(12) C11 0.0393(14) 0.0445(18) 0.0507(17) 0.0204(14) 0.0256(13) 0.0180(13) C12 0.0345(12) 0.0332(15) 0.0242(12) 0.0013(10) 0.0074(10) 0.0027(11) C13 0.0424(14) 0.0292(16) 0.0331(13) 0.0083(12) 0.0162(12) 0.0003(11) C14 0.0371(13) 0.0316(15) 0.0309(13) 0.0027(12) 0.0116(11) -0.0024(11) C15 0.0389(13) 0.0303(16) 0.0295(12) 0.0030(11) 0.0136(11) 0.0003(10) C16 0.0379(13) 0.0272(14) 0.0312(13) -0.0001(11) 0.0123(11) -0.0023(10) C17 0.0389(13) 0.0299(16) 0.0298(12) 0.0025(11) 0.0161(10) -0.0010(10) C18 0.0376(13) 0.0291(14) 0.0305(13) 0.0013(11) 0.0155(11) -0.0008(10) C19 0.0388(12) 0.0289(16) 0.0304(12) 0.0029(11) 0.0140(10) -0.0005(10) C20 0.0378(13) 0.0313(15) 0.0318(13) -0.0008(12) 0.0146(11) -0.0019(11) C21 0.0378(12) 0.0289(15) 0.0310(12) 0.0005(11) 0.0139(10) -0.0027(10) C22 0.0378(13) 0.0324(15) 0.0318(13) -0.0027(12) 0.0115(11) -0.0046(11) C23 0.0503(16) 0.0299(16) 0.0315(14) 0.0006(11) 0.0169(12) -0.0019(12) C24 0.063(2) 0.0442(19) 0.0433(17) -0.0025(15) 0.0300(16) -0.0051(17) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 O2 1.4353(17) . ? S1 O3 1.446(2) . ? S1 N2 1.5982(17) . ? S1 C6 1.784(2) . ? O1 C5 1.228(3) . ? O4 C12 1.333(3) . ? O4 C13 1.453(3) . ? O5 C12 1.195(3) . ? N1 C1 1.504(3) . ? N1 C4 1.508(3) . ? N1 H1N 0.89(4) . ? N1 H2N 0.84(4) . ? N2 C5 1.350(3) . ? C1 C2 1.498(4) . ? C1 H1A 0.94(3) . ? C1 H1B 0.99(3) . ? C2 C3 1.523(4) . ? C2 H2A 0.99(3) . ? C2 H2B 1.03(3) . ? C3 C4 1.545(4) . ? C3 H3A 0.90(3) . ? C3 H3B 0.92(4) . ? C4 C5 1.532(3) . ? C4 H4 0.98(2) . ? C6 C7 1.372(4) . ? C6 C11 1.373(3) . ? C7 C8 1.382(4) . ? C7 H7 0.86(4) . ? C8 C9 1.388(3) . ? C8 H8 0.97(3) . ? C9 C10 1.375(4) . ? C9 C12 1.496(3) . ? C10 C11 1.379(4) . ? C10 H10 0.96(3) . ? C11 H11 0.90(4) . ? C13 C14 1.499(4) . ? C13 H13A 0.90(3) . ? C13 H13B 0.93(3) . ? C14 C15 1.517(3) . ? C14 H14A 0.94(3) . ? C14 H14B 0.85(3) . ? C15 C16 1.521(4) . ? C15 H15A 0.91(3) . ? C15 H15B 0.97(4) . ? C16 C17 1.521(3) . ? C16 H16A 1.01(3) . ? C16 H16B 0.97(3) . ? C17 C18 1.520(3) . ? C17 H17A 1.01(4) . ? C17 H17B 1.06(3) . ? C18 C19 1.521(3) . ? C18 H18A 1.01(4) . ? C18 H18B 1.03(3) . ? C19 C20 1.517(3) . ? C19 H19A 1.00(3) . ? C19 H19B 1.10(3) . ? C20 C21 1.522(3) . ? C20 H20A 1.01(3) . ? C20 H20B 1.02(3) . ? C21 C22 1.517(4) . ? C21 H21A 1.00(3) . ? C21 H21B 1.02(3) . ? C22 C23 1.513(4) . ? C22 H22A 0.98(3) . ? C22 H22B 0.92(3) . ? C23 C24 1.515(4) . ? C23 H23A 1.02(4) . ? C23 H23B 0.84(3) . ? C24 H24A 0.87(4) . ? C24 H24B 0.87(5) . ? C24 H24C 0.99(5) . ? _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O2 S1 O3 115.57(11) . . ? O2 S1 N2 115.58(10) . . ? O3 S1 N2 105.40(11) . . ? O2 S1 C6 107.67(11) . . ? O3 S1 C6 106.46(11) . . ? N2 S1 C6 105.36(10) . . ? C12 O4 C13 117.0(2) . . ? C1 N1 C4 107.9(2) . . ? C1 N1 H1N 107(3) . . ? C4 N1 H1N 111(3) . . ? C1 N1 H2N 108(3) . . ? C4 N1 H2N 106(3) . . ? H1N N1 H2N 117(4) . . ? C5 N2 S1 118.90(17) . . ? C2 C1 N1 103.3(2) . . ? C2 C1 H1A 116.7(18) . . ? N1 C1 H1A 109.4(17) . . ? C2 C1 H1B 112.3(18) . . ? N1 C1 H1B 108.9(17) . . ? H1A C1 H1B 106(2) . . ? C1 C2 C3 103.4(2) . . ? C1 C2 H2A 112.3(18) . . ? C3 C2 H2A 110.0(17) . . ? C1 C2 H2B 112.2(18) . . ? C3 C2 H2B 115.8(18) . . ? H2A C2 H2B 103(2) . . ? C2 C3 C4 103.5(2) . . ? C2 C3 H3A 108(2) . . ? C4 C3 H3A 108(2) . . ? C2 C3 H3B 112(2) . . ? C4 C3 H3B 108(2) . . ? H3A C3 H3B 116(3) . . ? N1 C4 C5 107.5(2) . . ? N1 C4 C3 104.9(2) . . ? C5 C4 C3 114.0(2) . . ? N1 C4 H4 107.9(16) . . ? C5 C4 H4 110.5(14) . . ? C3 C4 H4 111.6(16) . . ? O1 C5 N2 128.7(2) . . ? O1 C5 C4 119.4(2) . . ? N2 C5 C4 111.9(2) . . ? C7 C6 C11 120.1(2) . . ? C7 C6 S1 121.48(18) . . ? C11 C6 S1 118.4(2) . . ? C6 C7 C8 120.1(2) . . ? C6 C7 H7 119(3) . . ? C8 C7 H7 121(3) . . ? C7 C8 C9 120.0(3) . . ? C7 C8 H8 120.3(19) . . ? C9 C8 H8 119.5(19) . . ? C10 C9 C8 119.3(2) . . ? C10 C9 C12 121.9(2) . . ? C8 C9 C12 118.7(2) . . ? C9 C10 C11 120.4(2) . . ? C9 C10 H10 118(2) . . ? C11 C10 H10 121(2) . . ? C6 C11 C10 120.1(3) . . ? C6 C11 H11 121(2) . . ? C10 C11 H11 119(2) . . ? O5 C12 O4 124.0(3) . . ? O5 C12 C9 124.6(2) . . ? O4 C12 C9 111.4(2) . . ? O4 C13 C14 107.8(2) . . ? O4 C13 H13A 107(2) . . ? C14 C13 H13A 111.0(19) . . ? O4 C13 H13B 109.6(17) . . ? C14 C13 H13B 106.7(17) . . ? H13A C13 H13B 115(3) . . ? C13 C14 C15 112.1(2) . . ? C13 C14 H14A 108.1(18) . . ? C15 C14 H14A 111.4(18) . . ? C13 C14 H14B 109(2) . . ? C15 C14 H14B 111(2) . . ? H14A C14 H14B 105(3) . . ? C14 C15 C16 113.8(2) . . ? C14 C15 H15A 109.5(19) . . ? C16 C15 H15A 108.2(19) . . ? C14 C15 H15B 107.7(19) . . ? C16 C15 H15B 107.3(19) . . ? H15A C15 H15B 110(3) . . ? C15 C16 C17 114.0(2) . . ? C15 C16 H16A 107.8(16) . . ? C17 C16 H16A 110.7(16) . . ? C15 C16 H16B 111.3(17) . . ? C17 C16 H16B 107.5(17) . . ? H16A C16 H16B 105(3) . . ? C18 C17 C16 113.7(2) . . ? C18 C17 H17A 108.2(19) . . ? C16 C17 H17A 108.3(19) . . ? C18 C17 H17B 109.7(17) . . ? C16 C17 H17B 107.0(17) . . ? H17A C17 H17B 110(3) . . ? C17 C18 C19 114.3(2) . . ? C17 C18 H18A 109.5(19) . . ? C19 C18 H18A 103.4(18) . . ? C17 C18 H18B 109.4(16) . . ? C19 C18 H18B 108.6(17) . . ? H18A C18 H18B 112(3) . . ? C20 C19 C18 113.8(2) . . ? C20 C19 H19A 107.5(17) . . ? C18 C19 H19A 109.3(17) . . ? C20 C19 H19B 109.4(15) . . ? C18 C19 H19B 108.4(15) . . ? H19A C19 H19B 108(3) . . ? C19 C20 C21 114.6(2) . . ? C19 C20 H20A 110.8(16) . . ? C21 C20 H20A 102.6(16) . . ? C19 C20 H20B 108.3(17) . . ? C21 C20 H20B 108.7(18) . . ? H20A C20 H20B 112(2) . . ? C22 C21 C20 113.0(2) . . ? C22 C21 H21A 107.4(17) . . ? C20 C21 H21A 111.8(17) . . ? C22 C21 H21B 108.6(15) . . ? C20 C21 H21B 109.5(15) . . ? H21A C21 H21B 106(2) . . ? C23 C22 C21 114.8(2) . . ? C23 C22 H22A 108.5(18) . . ? C21 C22 H22A 109.9(18) . . ? C23 C22 H22B 105(2) . . ? C21 C22 H22B 108(2) . . ? H22A C22 H22B 110(3) . . ? C22 C23 C24 112.6(2) . . ? C22 C23 H23A 106.5(18) . . ? C24 C23 H23A 109.2(19) . . ? C22 C23 H23B 107(2) . . ? C24 C23 H23B 106(2) . . ? H23A C23 H23B 116(3) . . ? C23 C24 H24A 111(2) . . ? C23 C24 H24B 114(3) . . ? H24A C24 H24B 108(4) . . ? C23 C24 H24C 108(2) . . ? H24A C24 H24C 106(4) . . ? H24B C24 H24C 111(3) . . ? _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O2 S1 N2 C5 -51.3(2) . . . . ? O3 S1 N2 C5 179.74(17) . . . . ? C6 S1 N2 C5 67.38(18) . . . . ? C4 N1 C1 C2 -27.0(3) . . . . ? N1 C1 C2 C3 40.5(3) . . . . ? C1 C2 C3 C4 -38.7(3) . . . . ? C1 N1 C4 C5 124.6(2) . . . . ? C1 N1 C4 C3 2.9(3) . . . . ? C2 C3 C4 N1 21.8(3) . . . . ? C2 C3 C4 C5 -95.5(2) . . . . ? S1 N2 C5 O1 3.8(3) . . . . ? S1 N2 C5 C4 -175.36(15) . . . . ? N1 C4 C5 O1 7.0(3) . . . . ? C3 C4 C5 O1 122.8(3) . . . . ? N1 C4 C5 N2 -173.75(19) . . . . ? C3 C4 C5 N2 -57.9(3) . . . . ? O2 S1 C6 C7 12.4(2) . . . . ? O3 S1 C6 C7 136.9(2) . . . . ? N2 S1 C6 C7 -111.4(2) . . . . ? O2 S1 C6 C11 -168.1(2) . . . . ? O3 S1 C6 C11 -43.6(2) . . . . ? N2 S1 C6 C11 68.0(2) . . . . ? C11 C6 C7 C8 -0.3(4) . . . . ? S1 C6 C7 C8 179.2(2) . . . . ? C6 C7 C8 C9 0.8(5) . . . . ? C7 C8 C9 C10 -0.8(4) . . . . ? C7 C8 C9 C12 -178.2(3) . . . . ? C8 C9 C10 C11 0.3(4) . . . . ? C12 C9 C10 C11 177.6(3) . . . . ? C7 C6 C11 C10 -0.2(5) . . . . ? S1 C6 C11 C10 -179.7(2) . . . . ? C9 C10 C11 C6 0.2(5) . . . . ? C13 O4 C12 O5 3.2(4) . . . . ? C13 O4 C12 C9 -176.0(2) . . . . ? C10 C9 C12 O5 -170.9(3) . . . . ? C8 C9 C12 O5 6.4(4) . . . . ? C10 C9 C12 O4 8.3(3) . . . . ? C8 C9 C12 O4 -174.4(3) . . . . ? C12 O4 C13 C14 -169.8(2) . . . . ? O4 C13 C14 C15 -177.8(2) . . . . ? C13 C14 C15 C16 -178.9(2) . . . . ? C14 C15 C16 C17 -179.7(2) . . . . ? C15 C16 C17 C18 -179.2(2) . . . . ? C16 C17 C18 C19 -179.3(2) . . . . ? C17 C18 C19 C20 -179.6(2) . . . . ? C18 C19 C20 C21 -179.1(2) . . . . ? C19 C20 C21 C22 -179.4(2) . . . . ? C20 C21 C22 C23 179.6(2) . . . . ? C21 C22 C23 C24 -177.0(3) . . . . ? _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1N N2 0.89(4) 2.12(4) 2.919(3) 149(3) 2_757 N1 H1N O3 0.89(4) 2.44(4) 3.144(3) 136(3) 2_757 N1 H2N O1 0.84(4) 2.09(4) 2.618(3) 120(3) . N1 H2N O2 0.84(4) 2.52(4) 3.125(3) 130(3) 2_657 _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.290 _refine_diff_density_min -0.279 _refine_diff_density_rms 0.084