# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full CrystEngComm _journal_coden_cambridge 1350 _journal_year ? _journal_volume ? _journal_page_first ? loop_ _publ_author_name _publ_author_address M.Carcu ; Babes-Bolyai University, Center of Supramolecular Organic and Organometallic Chemistry, Cluj-Napoca, 11 Arany Janos, 400028, Cluj-Napoca, Romania ; V.Pascanu ; Babes-Bolyai University, Center of Supramolecular Organic and Organometallic Chemistry, Cluj-Napoca, 11 Arany Janos, 400028, Cluj-Napoca, Romania ; A.Soran Romania' 'Beatrice Braun' ; Babes-Bolyai University, Center of Supramolecular Organic and Organometallic Chemistry, Cluj-Napoca, 11 Arany Janos, 400028, Cluj-Napoca, Romania ; A.Terec ; Babes-Bolyai University, Center of Supramolecular Organic and Organometallic Chemistry, Cluj-Napoca, 11 Arany Janos, 400028, Cluj-Napoca, Romania ; C.Socaci ; Babes-Bolyai University, Center of Supramolecular Organic and Organometallic Chemistry, Cluj-Napoca, 11 Arany Janos, 400028, Cluj-Napoca, Romania ; I.Grosu ; Babes-Bolyai University, Center of Supramolecular Organic and Organometallic Chemistry, Cluj-Napoca, 11 Arany Janos, 400028, Cluj-Napoca, Romania ; _publ_contact_author_address ; Babes-Bolyai University, Center of Supramolecular Organic and Organometallic Chemistry, Cluj-Napoca, 11 Arany Janos, 400028, Cluj-Napoca, Romania ; _publ_contact_author_email csocaci@chem.ubbcluj.ro _publ_contact_author_fax 40-264-590818 _publ_contact_author_phone 40-264-593833 _publ_contact_author_name 'Crina Socaci' data_r41_r3m _database_code_depnum_ccdc_archive 'CCDC 600990' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C13.50 H21 O3' _chemical_formula_weight 231.30 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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Trigonal _symmetry_space_group_name_H-M R3m loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z' '-x+y, -x, z' '-x+y, y, z' 'x, x-y, z' '-y, -x, z' 'x+2/3, y+1/3, z+1/3' '-y+2/3, x-y+1/3, z+1/3' '-x+y+2/3, -x+1/3, z+1/3' '-x+y+2/3, y+1/3, z+1/3' 'x+2/3, x-y+1/3, z+1/3' '-y+2/3, -x+1/3, z+1/3' 'x+1/3, y+2/3, z+2/3' '-y+1/3, x-y+2/3, z+2/3' '-x+y+1/3, -x+2/3, z+2/3' '-x+y+1/3, y+2/3, z+2/3' 'x+1/3, x-y+2/3, z+2/3' '-y+1/3, -x+2/3, z+2/3' _cell_length_a 15.8078(4) _cell_length_b 15.8078(4) _cell_length_c 9.2047(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 1991.97(10) _cell_formula_units_Z 6 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.55 _exptl_crystal_size_mid 0.45 _exptl_crystal_size_min 0.45 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.157 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 756 _exptl_absorpt_coefficient_mu 0.080 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type Nonius_KappaCCD _diffrn_measurement_method 'Area detector scans (see text)' _diffrn_detector_area_resol_mean 19.24 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 1017 _diffrn_reflns_av_R_equivalents 0.0084 _diffrn_reflns_av_sigmaI/netI 0.0178 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.58 _diffrn_reflns_theta_max 27.50 _reflns_number_total 567 _reflns_number_gt 556 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Nonius (1999)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution 'SIR-97_(Altomare & al., 1998)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON_(Spek, 1998)' _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^)+(0.0669P)^2^+0.6736P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.023(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -10(10) _refine_ls_number_reflns 567 _refine_ls_number_parameters 62 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0385 _refine_ls_R_factor_gt 0.0379 _refine_ls_wR_factor_ref 0.0973 _refine_ls_wR_factor_gt 0.0967 _refine_ls_goodness_of_fit_ref 1.137 _refine_ls_restrained_S_all 1.135 _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 O1 O 0.25551(8) 0.20230(8) 0.48164(11) 0.0177(4) Uani 1 1 d . . . C1 C 0.05088(8) -0.05088(8) 0.5290(3) 0.0185(5) Uani 1 2 d S . . H1 H 0.0848 -0.0848 0.5301 0.022 Uiso 1 2 calc SR . . C2 C 0.10229(16) 0.05114(8) 0.5283(2) 0.0172(5) Uani 1 2 d S . . C3 C 0.21378(16) 0.10689(8) 0.5422(2) 0.0164(5) Uani 1 2 d S . . C4 C 0.25174(13) 0.20290(11) 0.32524(17) 0.0189(4) Uani 1 1 d . . . H4A H 0.2830 0.2698 0.2907 0.023 Uiso 1 1 calc R . . H4B H 0.1842 0.1700 0.2936 0.023 Uiso 1 1 calc R . . C6 C 0.24388(19) 0.12194(9) 0.7012(2) 0.0234(5) Uani 1 2 d S . . H6A H 0.2179 0.0596 0.7482 0.035 Uiso 0.50 1 calc PR . . H6B H 0.2189 0.1593 0.7478 0.035 Uiso 0.50 1 calc PR . . H6C H 0.3139 0.1564 0.7080 0.035 Uiso 1 2 calc SR . . C5 C 0.30324(16) 0.15162(8) 0.2602(3) 0.0202(5) Uani 1 2 d S . . C7 C 0.41129(18) 0.20565(9) 0.3017(3) 0.0243(5) Uani 1 2 d S . . H7A H 0.4174 0.2088 0.4056 0.036 Uiso 1 2 calc SR . . H7B H 0.4422 0.2707 0.2627 0.036 Uiso 0.50 1 calc PR . . H7C H 0.4422 0.1715 0.2628 0.036 Uiso 0.50 1 calc PR . . C8 C 0.2909(2) 0.14544(12) 0.0957(3) 0.0299(6) Uani 1 2 d S . . H8A H 0.2226 0.1115 0.0721 0.045 Uiso 1 2 calc SR . . H8B H 0.3209 0.1108 0.0557 0.045 Uiso 0.50 1 calc PR . . H8C H 0.3214 0.2102 0.0557 0.045 Uiso 0.50 1 calc PR . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0172(6) 0.0142(6) 0.0206(6) -0.0009(4) 0.0005(4) 0.0070(4) C1 0.0171(8) 0.0171(8) 0.0219(10) 0.0002(4) -0.0002(4) 0.0089(9) C2 0.0152(10) 0.0174(8) 0.0181(10) -0.0005(4) -0.0009(8) 0.0076(5) C3 0.0158(11) 0.0145(7) 0.0194(11) 0.0005(4) 0.0011(8) 0.0079(5) C4 0.0216(8) 0.0185(8) 0.0191(8) 0.0024(6) 0.0002(6) 0.0119(6) C6 0.0231(12) 0.0245(9) 0.0222(12) -0.0003(4) -0.0005(9) 0.0115(6) C5 0.0218(11) 0.0189(8) 0.0208(11) 0.0009(4) 0.0018(9) 0.0109(6) C7 0.0208(12) 0.0232(9) 0.0279(13) 0.0024(5) 0.0048(9) 0.0104(6) C8 0.0382(15) 0.0337(10) 0.0193(13) -0.0003(5) -0.0006(10) 0.0191(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C3 1.4234(15) . ? O1 C4 1.4410(18) . ? C1 C2 1.3967(15) 3 ? C1 C2 1.3967(15) . ? C1 H1 0.9300 . ? C2 C1 1.3967(15) 2 ? C2 C3 1.532(3) . ? C3 O1 1.4234(15) 5 ? C3 C6 1.520(3) . ? C4 C5 1.529(2) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C6 H6A 0.9600 . ? C6 H6B 0.9600 . ? C6 H6C 0.9600 . ? C5 C8 1.524(3) . ? C5 C7 1.528(3) . ? C5 C4 1.529(2) 5 ? C7 H7A 0.9600 . ? C7 H7B 0.9600 . ? C7 H7C 0.9600 . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C3 O1 C4 113.56(12) . . ? C2 C1 C2 120.5(2) 3 . ? C2 C1 H1 119.7 3 . ? C2 C1 H1 119.7 . . ? C1 C2 C1 119.5(2) 2 . ? C1 C2 C3 120.11(11) 2 . ? C1 C2 C3 120.11(11) . . ? O1 C3 O1 111.76(16) . 5 ? O1 C3 C6 105.57(12) . . ? O1 C3 C6 105.57(12) 5 . ? O1 C3 C2 111.53(11) . . ? O1 C3 C2 111.53(11) 5 . ? C6 C3 C2 110.54(18) . . ? O1 C4 C5 110.66(14) . . ? O1 C4 H4A 109.5 . . ? C5 C4 H4A 109.5 . . ? O1 C4 H4B 109.5 . . ? C5 C4 H4B 109.5 . . ? H4A C4 H4B 108.1 . . ? C3 C6 H6A 109.5 . . ? C3 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C3 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C8 C5 C7 110.84(19) . . ? C8 C5 C4 109.74(14) . 5 ? C7 C5 C4 110.41(13) . 5 ? C8 C5 C4 109.74(14) . . ? C7 C5 C4 110.41(13) . . ? C4 C5 C4 105.57(17) 5 . ? C5 C7 H7A 109.5 . . ? C5 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C5 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C5 C8 H8A 109.5 . . ? C5 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C5 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C2 C1 C2 C1 1.0(4) 3 . . 2 ? C2 C1 C2 C3 174.77(15) 3 . . . ? C4 O1 C3 O1 53.8(2) . . . 5 ? C4 O1 C3 C6 168.08(14) . . . . ? C4 O1 C3 C2 -71.82(17) . . . . ? C1 C2 C3 O1 -30.3(3) 2 . . . ? C1 C2 C3 O1 156.00(17) . . . . ? C1 C2 C3 O1 -156.00(17) 2 . . 5 ? C1 C2 C3 O1 30.3(3) . . . 5 ? C1 C2 C3 C6 86.87(18) 2 . . . ? C1 C2 C3 C6 -86.87(18) . . . . ? C3 O1 C4 C5 -57.42(16) . . . . ? O1 C4 C5 C8 175.20(16) . . . . ? O1 C4 C5 C7 -62.34(17) . . . . ? O1 C4 C5 C4 57.0(2) . . . 5 ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.238 _refine_diff_density_min -0.246 _refine_diff_density_rms 0.075 data_123alb _database_code_depnum_ccdc_archive 'CCDC 832243' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C21 H21 N O3' _chemical_formula_sum 'C21 H21 N O3' _chemical_formula_weight 335.39 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/n ' _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 13.076(6) _cell_length_b 6.162(3) _cell_length_c 23.616(12) _cell_angle_alpha 90.00 _cell_angle_beta 102.183(9) _cell_angle_gamma 90.00 _cell_volume 1859.9(15) _cell_formula_units_Z 4 _cell_measurement_temperature 297(2) _cell_measurement_reflns_used 2975 _cell_measurement_theta_min 2.79 _cell_measurement_theta_max 23.21 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.49 _exptl_crystal_size_mid 0.45 _exptl_crystal_size_min 0.31 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.198 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 712 _exptl_absorpt_coefficient_mu 0.080 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9619 _exptl_absorpt_correction_T_max 0.9756 _exptl_absorpt_process_details 'Bruker, 2001.' _exptl_special_details ; ? ; _diffrn_ambient_temperature 297(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type '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 8467 _diffrn_reflns_av_R_equivalents 0.0337 _diffrn_reflns_av_sigmaI/netI 0.0476 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 1.65 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3279 _reflns_number_gt 2309 _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 'DIAMOND 3 (Brandenburg, 2006)' _computing_publication_material 'enCIFer (CCDC, 2003)' _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^)+(0.0637P)^2^+0.8918P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3279 _refine_ls_number_parameters 226 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1076 _refine_ls_R_factor_gt 0.0752 _refine_ls_wR_factor_ref 0.1801 _refine_ls_wR_factor_gt 0.1661 _refine_ls_goodness_of_fit_ref 1.108 _refine_ls_restrained_S_all 1.108 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.09741(13) 0.7453(4) 0.39643(7) 0.0544(8) Uani 1 1 d G . . C2 C 0.06692(14) 0.5620(4) 0.42295(9) 0.0805(11) Uani 1 1 d G . . H2 H 0.0009 0.5024 0.4094 0.097 Uiso 1 1 calc R . . C3 C 0.13503(19) 0.4679(3) 0.46966(9) 0.0819(11) Uani 1 1 d G . . H3 H 0.1146 0.3452 0.4874 0.098 Uiso 1 1 calc R . . C4 C 0.23364(17) 0.5570(3) 0.48986(7) 0.0619(9) Uani 1 1 d G . . C5 C 0.26412(13) 0.7403(3) 0.46335(8) 0.0624(9) Uani 1 1 d G . . H5 H 0.3301 0.8000 0.4769 0.075 Uiso 1 1 calc R . . C6 C 0.19601(15) 0.8345(3) 0.41663(8) 0.0589(8) Uani 1 1 d G . . H6 H 0.2164 0.9571 0.3989 0.071 Uiso 1 1 calc R . . C7 C 0.3110(3) 0.4481(6) 0.53856(14) 0.0836(12) Uani 1 1 d . . . H7A H 0.3651 0.5505 0.5557 0.100 Uiso 1 1 calc R . . H7B H 0.2754 0.4002 0.5684 0.100 Uiso 1 1 calc R . . C8 C 0.0649(2) 0.8482(6) 0.29334(11) 0.0537(8) Uani 1 1 d . . . C9 C 0.1255(2) 0.6859(5) 0.27717(12) 0.0556(8) Uani 1 1 d . . . H9 H 0.1461 0.5686 0.3017 0.067 Uiso 1 1 calc R . . C10 C 0.1559(2) 0.6970(6) 0.22447(12) 0.0583(9) Uani 1 1 d . . . H10 H 0.1975 0.5868 0.2145 0.070 Uiso 1 1 calc R . . C11 C 0.1267(2) 0.8654(6) 0.18661(12) 0.0559(8) Uani 1 1 d . . . C12 C 0.0676(3) 1.0295(6) 0.20329(13) 0.0674(10) Uani 1 1 d . . . H12 H 0.0476 1.1468 0.1786 0.081 Uiso 1 1 calc R . . C13 C 0.0375(3) 1.0228(6) 0.25627(13) 0.0659(9) Uani 1 1 d . . . H13 H -0.0014 1.1364 0.2669 0.079 Uiso 1 1 calc R . . C14 C 0.1559(3) 0.8743(7) 0.12845(14) 0.0808(12) Uani 1 1 d . . . H14A H 0.1449 1.0202 0.1129 0.097 Uiso 1 1 calc R . . H14B H 0.2295 0.8394 0.1328 0.097 Uiso 1 1 calc R . . C15 C -0.0744(2) 0.8852(5) 0.34797(11) 0.0530(8) Uani 1 1 d . . . C16 C -0.1542(2) 0.8326(6) 0.30226(13) 0.0659(10) Uani 1 1 d . . . H16 H -0.1390 0.7612 0.2703 0.079 Uiso 1 1 calc R . . C17 C -0.2565(2) 0.8842(6) 0.30306(13) 0.0628(9) Uani 1 1 d . . . H17 H -0.3093 0.8439 0.2719 0.075 Uiso 1 1 calc R . . C18 C -0.2823(2) 0.9929(5) 0.34851(12) 0.0541(8) Uani 1 1 d . . . C19 C -0.2020(3) 1.0424(6) 0.39502(13) 0.0669(10) Uani 1 1 d . . . H19 H -0.2174 1.1126 0.4271 0.080 Uiso 1 1 calc R . . C20 C -0.0999(2) 0.9899(6) 0.39478(12) 0.0634(9) Uani 1 1 d . . . H20 H -0.0473 1.0253 0.4265 0.076 Uiso 1 1 calc R . . C21 C -0.3925(2) 1.0659(7) 0.34633(13) 0.0720(11) Uani 1 1 d . . . H21A H -0.3956 1.2230 0.3438 0.086 Uiso 1 1 calc R . . H21B H -0.4377 1.0078 0.3117 0.086 Uiso 1 1 calc R . . N1 N 0.03119(19) 0.8389(5) 0.34664(10) 0.0686(9) Uani 1 1 d . . . O1 O 0.3558(2) 0.2707(5) 0.51631(11) 0.0925(10) Uani 1 1 d . . . O2 O 0.0967(2) 0.7299(5) 0.09032(10) 0.0876(9) Uani 1 1 d . . . O3 O -0.4292(2) 0.9990(5) 0.39470(11) 0.0890(10) Uani 1 1 d . . . H22 H 0.376(2) 0.188(6) 0.5401(14) 0.062(11) Uiso 1 1 d . . . H23 H -0.478(3) 1.066(6) 0.3977(16) 0.092(14) Uiso 1 1 d . . . H24 H 0.110(3) 0.735(6) 0.0564(17) 0.092(12) 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 C1 0.0525(18) 0.075(2) 0.0417(15) 0.0069(15) 0.0235(14) 0.0137(17) C2 0.063(2) 0.105(3) 0.077(2) 0.025(2) 0.0234(19) -0.001(2) C3 0.093(3) 0.085(3) 0.074(2) 0.027(2) 0.030(2) 0.000(2) C4 0.086(2) 0.064(2) 0.0371(15) -0.0014(15) 0.0170(16) 0.0234(19) C5 0.070(2) 0.067(2) 0.0468(17) -0.0048(16) 0.0063(15) 0.0090(18) C6 0.068(2) 0.061(2) 0.0501(17) 0.0041(15) 0.0175(15) 0.0042(17) C7 0.123(3) 0.078(3) 0.0483(19) 0.0043(18) 0.016(2) 0.039(2) C8 0.0445(16) 0.078(2) 0.0416(15) 0.0071(15) 0.0170(13) 0.0113(16) C9 0.0481(17) 0.073(2) 0.0469(16) 0.0072(15) 0.0133(13) 0.0133(16) C10 0.0445(17) 0.080(3) 0.0531(18) -0.0135(17) 0.0171(14) 0.0037(16) C11 0.0483(17) 0.077(2) 0.0465(16) -0.0071(17) 0.0202(14) -0.0162(17) C12 0.077(2) 0.075(3) 0.0543(19) 0.0121(17) 0.0222(17) -0.005(2) C13 0.072(2) 0.074(3) 0.0579(19) 0.0070(17) 0.0272(16) 0.0181(18) C14 0.083(2) 0.112(3) 0.058(2) -0.020(2) 0.0368(18) -0.038(2) C15 0.0501(17) 0.074(2) 0.0391(15) 0.0044(14) 0.0174(13) 0.0139(16) C16 0.062(2) 0.091(3) 0.0487(18) -0.0193(17) 0.0212(15) 0.0116(19) C17 0.0519(19) 0.086(3) 0.0507(18) -0.0089(17) 0.0105(14) 0.0005(17) C18 0.0500(17) 0.068(2) 0.0481(17) 0.0077(15) 0.0179(14) 0.0124(16) C19 0.065(2) 0.090(3) 0.0517(18) -0.0149(17) 0.0268(16) 0.0183(19) C20 0.0520(18) 0.094(3) 0.0448(16) -0.0138(17) 0.0118(14) 0.0076(18) C21 0.057(2) 0.104(3) 0.060(2) 0.0146(19) 0.0254(16) 0.0234(19) N1 0.0519(15) 0.117(3) 0.0432(14) 0.0167(15) 0.0239(12) 0.0281(16) O1 0.132(2) 0.100(2) 0.0516(14) 0.0270(15) 0.0338(15) 0.0612(19) O2 0.0902(18) 0.133(2) 0.0487(13) -0.0211(15) 0.0341(13) -0.0581(17) O3 0.0741(17) 0.130(2) 0.0775(16) 0.0481(16) 0.0489(14) 0.0570(17) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.3900 . ? C1 C6 1.3900 . ? C1 N1 1.427(3) . ? C2 C3 1.3900 . ? C2 H2 0.9300 . ? C3 C4 1.3900 . ? C3 H3 0.9300 . ? C4 C5 1.3900 . ? C4 C7 1.518(4) . ? C5 C6 1.3900 . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C7 O1 1.394(4) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C9 1.380(4) . ? C8 C13 1.386(4) . ? C8 N1 1.420(3) . ? C9 C10 1.386(4) . ? C9 H9 0.9300 . ? C10 C11 1.370(4) . ? C10 H10 0.9300 . ? C11 C12 1.380(5) . ? C11 C14 1.502(4) . ? C12 C13 1.389(4) . ? C12 H12 0.9300 . ? C13 H13 0.9300 . ? C14 O2 1.381(4) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C15 C16 1.372(4) . ? C15 C20 1.379(4) . ? C15 N1 1.417(4) . ? C16 C17 1.379(4) . ? C16 H16 0.9300 . ? C17 C18 1.367(4) . ? C17 H17 0.9300 . ? C18 C19 1.384(4) . ? C18 C21 1.501(4) . ? C19 C20 1.375(4) . ? C19 H19 0.9300 . ? C20 H20 0.9300 . ? C21 O3 1.391(4) . ? C21 H21A 0.9700 . ? C21 H21B 0.9700 . ? O1 H22 0.76(3) . ? O2 H24 0.85(4) . ? O3 H23 0.78(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 C2 C1 C6 120.0 . . ? C2 C1 N1 121.20(19) . . ? C6 C1 N1 118.73(18) . . ? C1 C2 C3 120.0 . . ? C1 C2 H2 120.0 . . ? C3 C2 H2 120.0 . . ? C4 C3 C2 120.0 . . ? C4 C3 H3 120.0 . . ? C2 C3 H3 120.0 . . ? C5 C4 C3 120.0 . . ? C5 C4 C7 119.5(2) . . ? C3 C4 C7 120.5(2) . . ? C6 C5 C4 120.0 . . ? C6 C5 H5 120.0 . . ? C4 C5 H5 120.0 . . ? C5 C6 C1 120.0 . . ? C5 C6 H6 120.0 . . ? C1 C6 H6 120.0 . . ? O1 C7 C4 109.1(3) . . ? O1 C7 H7A 109.9 . . ? C4 C7 H7A 109.9 . . ? O1 C7 H7B 109.9 . . ? C4 C7 H7B 109.9 . . ? H7A C7 H7B 108.3 . . ? C9 C8 C13 118.4(3) . . ? C9 C8 N1 121.4(3) . . ? C13 C8 N1 120.3(3) . . ? C8 C9 C10 120.2(3) . . ? C8 C9 H9 119.9 . . ? C10 C9 H9 119.9 . . ? C11 C10 C9 122.0(3) . . ? C11 C10 H10 119.0 . . ? C9 C10 H10 119.0 . . ? C10 C11 C12 117.7(3) . . ? C10 C11 C14 122.3(3) . . ? C12 C11 C14 120.0(3) . . ? C11 C12 C13 121.2(3) . . ? C11 C12 H12 119.4 . . ? C13 C12 H12 119.4 . . ? C8 C13 C12 120.5(3) . . ? C8 C13 H13 119.8 . . ? C12 C13 H13 119.8 . . ? O2 C14 C11 110.9(3) . . ? O2 C14 H14A 109.5 . . ? C11 C14 H14A 109.5 . . ? O2 C14 H14B 109.5 . . ? C11 C14 H14B 109.5 . . ? H14A C14 H14B 108.0 . . ? C16 C15 C20 118.0(3) . . ? C16 C15 N1 121.1(3) . . ? C20 C15 N1 120.8(3) . . ? C15 C16 C17 120.9(3) . . ? C15 C16 H16 119.6 . . ? C17 C16 H16 119.6 . . ? C18 C17 C16 121.6(3) . . ? C18 C17 H17 119.2 . . ? C16 C17 H17 119.2 . . ? C17 C18 C19 117.4(3) . . ? C17 C18 C21 120.9(3) . . ? C19 C18 C21 121.6(3) . . ? C20 C19 C18 121.3(3) . . ? C20 C19 H19 119.4 . . ? C18 C19 H19 119.4 . . ? C19 C20 C15 120.8(3) . . ? C19 C20 H20 119.6 . . ? C15 C20 H20 119.6 . . ? O3 C21 C18 112.2(3) . . ? O3 C21 H21A 109.2 . . ? C18 C21 H21A 109.2 . . ? O3 C21 H21B 109.2 . . ? C18 C21 H21B 109.2 . . ? H21A C21 H21B 107.9 . . ? C15 N1 C8 119.9(2) . . ? C15 N1 C1 119.2(2) . . ? C8 N1 C1 119.9(2) . . ? C7 O1 H22 111(2) . . ? C14 O2 H24 113(2) . . ? C21 O3 H23 111(3) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 0.0 . . . . ? N1 C1 C2 C3 176.8(2) . . . . ? C1 C2 C3 C4 0.0 . . . . ? C2 C3 C4 C5 0.0 . . . . ? C2 C3 C4 C7 -176.4(2) . . . . ? C3 C4 C5 C6 0.0 . . . . ? C7 C4 C5 C6 176.5(2) . . . . ? C4 C5 C6 C1 0.0 . . . . ? C2 C1 C6 C5 0.0 . . . . ? N1 C1 C6 C5 -176.9(2) . . . . ? C5 C4 C7 O1 -98.6(3) . . . . ? C3 C4 C7 O1 77.8(3) . . . . ? C13 C8 C9 C10 -1.3(5) . . . . ? N1 C8 C9 C10 178.9(3) . . . . ? C8 C9 C10 C11 -0.7(5) . . . . ? C9 C10 C11 C12 1.8(5) . . . . ? C9 C10 C11 C14 -177.6(3) . . . . ? C10 C11 C12 C13 -1.0(5) . . . . ? C14 C11 C12 C13 178.5(3) . . . . ? C9 C8 C13 C12 2.2(5) . . . . ? N1 C8 C13 C12 -178.1(3) . . . . ? C11 C12 C13 C8 -1.0(5) . . . . ? C10 C11 C14 O2 74.4(4) . . . . ? C12 C11 C14 O2 -105.0(4) . . . . ? C20 C15 C16 C17 0.4(5) . . . . ? N1 C15 C16 C17 -178.0(3) . . . . ? C15 C16 C17 C18 1.4(6) . . . . ? C16 C17 C18 C19 -2.4(5) . . . . ? C16 C17 C18 C21 174.3(3) . . . . ? C17 C18 C19 C20 1.9(5) . . . . ? C21 C18 C19 C20 -174.9(3) . . . . ? C18 C19 C20 C15 -0.2(6) . . . . ? C16 C15 C20 C19 -1.0(5) . . . . ? N1 C15 C20 C19 177.4(3) . . . . ? C17 C18 C21 O3 128.1(4) . . . . ? C19 C18 C21 O3 -55.3(5) . . . . ? C16 C15 N1 C8 33.5(5) . . . . ? C20 C15 N1 C8 -144.8(3) . . . . ? C16 C15 N1 C1 -135.1(3) . . . . ? C20 C15 N1 C1 46.6(5) . . . . ? C9 C8 N1 C15 -133.9(3) . . . . ? C13 C8 N1 C15 46.4(5) . . . . ? C9 C8 N1 C1 34.6(4) . . . . ? C13 C8 N1 C1 -145.1(3) . . . . ? C2 C1 N1 C15 50.7(3) . . . . ? C6 C1 N1 C15 -132.4(3) . . . . ? C2 C1 N1 C8 -117.8(3) . . . . ? C6 C1 N1 C8 59.1(3) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.177 _refine_diff_density_min -0.192 _refine_diff_density_rms 0.037 # Attachment '832244.cif' data_129alb _database_code_depnum_ccdc_archive 'CCDC 832244' #TrackingRef '832244.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C27 H42 O9' _chemical_formula_sum 'C27 H42 O9' _chemical_formula_weight 510.61 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P2(1)/n ' _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 6.9496(7) _cell_length_b 17.9193(19) _cell_length_c 22.411(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.750(2) _cell_angle_gamma 90.00 _cell_volume 2790.6(5) _cell_formula_units_Z 4 _cell_measurement_temperature 297(2) _cell_measurement_reflns_used 4195 _cell_measurement_theta_min 2.27 _cell_measurement_theta_max 26.35 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.58 _exptl_crystal_size_mid 0.36 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.215 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1104 _exptl_absorpt_coefficient_mu 0.090 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9495 _exptl_absorpt_correction_T_max 0.9822 _exptl_absorpt_process_details 'Bruker, 2001.' _exptl_special_details ; ? ; _diffrn_ambient_temperature 297(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type '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 19896 _diffrn_reflns_av_R_equivalents 0.0629 _diffrn_reflns_av_sigmaI/netI 0.0611 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 1.82 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4907 _reflns_number_gt 3725 _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 'DIAMOND 3 (Brandenburg, 2006)' _computing_publication_material 'enCIFer (CCDC, 2003)' _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^)+(0.0863P)^2^+4.2400P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4907 _refine_ls_number_parameters 332 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1420 _refine_ls_R_factor_gt 0.1097 _refine_ls_wR_factor_ref 0.2485 _refine_ls_wR_factor_gt 0.2311 _refine_ls_goodness_of_fit_ref 1.179 _refine_ls_restrained_S_all 1.179 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.0874(6) 0.2399(2) 0.29013(17) 0.0259(9) Uani 1 1 d . . . C2 C 0.0237(5) 0.1748(2) 0.26341(17) 0.0249(9) Uani 1 1 d . . . H2 H 0.0497 0.1293 0.2817 0.030 Uiso 1 1 calc R . . C3 C -0.0778(5) 0.1760(2) 0.21014(16) 0.0243(9) Uani 1 1 d . . . C4 C -0.1207(5) 0.2437(2) 0.18378(17) 0.0230(9) Uani 1 1 d . . . H4 H -0.1888 0.2449 0.1478 0.028 Uiso 1 1 calc R . . C5 C -0.0633(5) 0.3101(2) 0.21050(16) 0.0233(9) Uani 1 1 d . . . C6 C 0.0415(6) 0.3077(2) 0.26318(16) 0.0259(9) Uani 1 1 d . . . H6 H 0.0822 0.3520 0.2809 0.031 Uiso 1 1 calc R . . C7 C 0.2141(6) 0.2357(2) 0.34640(17) 0.0276(9) Uani 1 1 d . . . C8 C 0.0425(7) 0.3188(3) 0.4089(2) 0.0431(12) Uani 1 1 d . . . H8A H -0.0615 0.3257 0.3802 0.052 Uiso 1 1 calc R . . H8B H 0.0574 0.3648 0.4313 0.052 Uiso 1 1 calc R . . C9 C -0.0103(7) 0.2557(3) 0.45178(19) 0.0414(12) Uani 1 1 d . . . C10 C -0.0157(7) 0.1862(3) 0.41386(19) 0.0408(12) Uani 1 1 d . . . H10A H -0.0405 0.1433 0.4390 0.049 Uiso 1 1 calc R . . H10B H -0.1203 0.1900 0.3849 0.049 Uiso 1 1 calc R . . C11 C 0.1396(9) 0.2495(3) 0.5015(2) 0.0617(16) Uani 1 1 d . . . H11A H 0.1107 0.2072 0.5262 0.092 Uiso 1 1 calc R . . H11B H 0.1381 0.2940 0.5253 0.092 Uiso 1 1 calc R . . H11C H 0.2647 0.2432 0.4845 0.092 Uiso 1 1 calc R . . C12 C -0.2096(9) 0.2705(4) 0.4773(3) 0.0767(19) Uani 1 1 d . . . H12A H -0.2978 0.2824 0.4454 0.115 Uiso 1 1 calc R . . H12B H -0.2025 0.3115 0.5047 0.115 Uiso 1 1 calc R . . H12C H -0.2536 0.2268 0.4978 0.115 Uiso 1 1 calc R . . C13 C 0.4191(7) 0.2171(3) 0.3308(2) 0.0474(13) Uani 1 1 d . . . H13A H 0.4999 0.2264 0.3656 0.057 Uiso 1 1 calc R . . H13B H 0.4262 0.1641 0.3221 0.057 Uiso 1 1 calc R . . C14 C -0.1642(6) 0.1046(2) 0.18399(17) 0.0250(9) Uani 1 1 d . . . C15 C 0.1274(6) 0.0343(2) 0.17474(18) 0.0315(10) Uani 1 1 d . . . H15A H 0.1905 -0.0111 0.1880 0.038 Uiso 1 1 calc R . . H15B H 0.2076 0.0762 0.1866 0.038 Uiso 1 1 calc R . . C16 C 0.1048(6) 0.0331(2) 0.10728(18) 0.0327(10) Uani 1 1 d . . . C17 C -0.0051(7) 0.1039(2) 0.09188(18) 0.0352(11) Uani 1 1 d . . . H17A H 0.0719 0.1469 0.1031 0.042 Uiso 1 1 calc R . . H17B H -0.0278 0.1059 0.0491 0.042 Uiso 1 1 calc R . . C18 C -0.0040(7) -0.0359(3) 0.0871(2) 0.0457(13) Uani 1 1 d . . . H18A H -0.1309 -0.0353 0.1035 0.069 Uiso 1 1 calc R . . H18B H 0.0631 -0.0797 0.1008 0.069 Uiso 1 1 calc R . . H18C H -0.0131 -0.0366 0.0444 0.069 Uiso 1 1 calc R . . C19 C 0.3036(7) 0.0361(3) 0.0797(2) 0.0526(14) Uani 1 1 d . . . H19A H 0.2909 0.0380 0.0370 0.079 Uiso 1 1 calc R . . H19B H 0.3750 -0.0077 0.0910 0.079 Uiso 1 1 calc R . . H19C H 0.3703 0.0797 0.0937 0.079 Uiso 1 1 calc R . . C20 C -0.3656(6) 0.0913(2) 0.2090(2) 0.0367(11) Uani 1 1 d U . . H20A H -0.4150 0.0442 0.1939 0.044 Uiso 1 1 calc R . . H20B H -0.3569 0.0877 0.2521 0.044 Uiso 1 1 calc R . . C21 C -0.1396(6) 0.3835(2) 0.18625(17) 0.0247(9) Uani 1 1 d . . . C22 C 0.0083(7) 0.3845(3) 0.09152(19) 0.0410(12) Uani 1 1 d . . . H22A H -0.0199 0.3839 0.0490 0.049 Uiso 1 1 calc R . . H22B H 0.0845 0.3407 0.1010 0.049 Uiso 1 1 calc R . . C23 C 0.1227(7) 0.4540(3) 0.10695(19) 0.0405(12) Uani 1 1 d . . . C24 C 0.1512(7) 0.4504(3) 0.17466(19) 0.0375(11) Uani 1 1 d . . . H24A H 0.2294 0.4073 0.1849 0.045 Uiso 1 1 calc R . . H24B H 0.2194 0.4947 0.1881 0.045 Uiso 1 1 calc R . . C25 C 0.3177(8) 0.4515(4) 0.0771(2) 0.0712(18) Uani 1 1 d . . . H25A H 0.3860 0.4076 0.0898 0.107 Uiso 1 1 calc R . . H25B H 0.3904 0.4951 0.0881 0.107 Uiso 1 1 calc R . . H25C H 0.2998 0.4503 0.0346 0.107 Uiso 1 1 calc R . . C26 C 0.0135(9) 0.5248(3) 0.0899(2) 0.0559(15) Uani 1 1 d . . . H26A H -0.0142 0.5245 0.0478 0.084 Uiso 1 1 calc R . . H26B H 0.0908 0.5676 0.0996 0.084 Uiso 1 1 calc R . . H26C H -0.1047 0.5270 0.1115 0.084 Uiso 1 1 calc R . . C27 C -0.3416(7) 0.3972(3) 0.2093(2) 0.0403(11) Uani 1 1 d . . . H27A H -0.3866 0.4454 0.1952 0.048 Uiso 1 1 calc R . . H27B H -0.4275 0.3593 0.1932 0.048 Uiso 1 1 calc R . . O1 O 0.1593(4) 0.17519(15) 0.38350(12) 0.0324(7) Uani 1 1 d . . . O2 O 0.2148(4) 0.30364(16) 0.37822(12) 0.0374(8) Uani 1 1 d . . . O3 O 0.4945(5) 0.25555(19) 0.28333(16) 0.0576(10) Uani 1 1 d . . . H3 H 0.4930 0.3004 0.2905 0.086 Uiso 1 1 calc R . . O4 O -0.1839(4) 0.10703(15) 0.12160(11) 0.0302(7) Uani 1 1 d . . . O5 O -0.0583(4) 0.04058(14) 0.20266(11) 0.0267(7) Uani 1 1 d . . . O6 O -0.4960(5) 0.1496(2) 0.19306(17) 0.0619(11) Uani 1 1 d U . . H6A H -0.4562 0.1893 0.2065 0.093 Uiso 1 1 calc R . . O7 O -0.0275(4) 0.44557(14) 0.20429(11) 0.0308(7) Uani 1 1 d . . . O8 O -0.1679(4) 0.38209(15) 0.12375(12) 0.0322(7) Uani 1 1 d . . . O9 O -0.3487(5) 0.39566(17) 0.27210(14) 0.0503(10) Uani 1 1 d . . . H9 H -0.3581 0.4384 0.2848 0.075 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.026(2) 0.024(2) 0.028(2) -0.0032(17) 0.0058(17) -0.0040(17) C2 0.026(2) 0.019(2) 0.029(2) 0.0030(17) 0.0063(17) 0.0018(17) C3 0.021(2) 0.024(2) 0.028(2) 0.0013(17) 0.0094(17) -0.0040(17) C4 0.021(2) 0.026(2) 0.0223(19) -0.0024(17) 0.0023(16) -0.0019(17) C5 0.022(2) 0.022(2) 0.026(2) 0.0009(16) 0.0099(16) -0.0019(17) C6 0.033(2) 0.018(2) 0.027(2) -0.0022(16) 0.0019(18) -0.0030(17) C7 0.027(2) 0.033(2) 0.023(2) -0.0050(17) -0.0007(17) -0.0005(18) C8 0.064(3) 0.030(3) 0.036(3) -0.011(2) 0.004(2) 0.008(2) C9 0.048(3) 0.048(3) 0.028(2) -0.006(2) 0.007(2) -0.003(2) C10 0.048(3) 0.043(3) 0.031(2) 0.008(2) 0.008(2) -0.009(2) C11 0.084(4) 0.068(4) 0.033(3) 0.001(3) -0.007(3) -0.008(3) C12 0.073(4) 0.100(5) 0.058(4) -0.014(3) 0.024(3) 0.006(4) C13 0.036(3) 0.068(4) 0.038(3) 0.001(2) -0.002(2) -0.002(3) C14 0.027(2) 0.018(2) 0.030(2) -0.0036(16) -0.0008(17) -0.0044(17) C15 0.033(3) 0.024(2) 0.038(2) -0.0036(18) 0.0008(19) 0.0025(19) C16 0.046(3) 0.024(2) 0.029(2) -0.0053(18) 0.005(2) -0.0009(19) C17 0.047(3) 0.034(3) 0.024(2) -0.0027(18) 0.0032(19) -0.002(2) C18 0.064(4) 0.033(3) 0.040(3) -0.012(2) 0.001(2) 0.001(2) C19 0.050(3) 0.056(3) 0.052(3) -0.004(3) 0.013(3) 0.011(3) C20 0.031(3) 0.023(2) 0.056(3) -0.004(2) 0.005(2) -0.0066(19) C21 0.030(2) 0.017(2) 0.027(2) -0.0025(16) -0.0025(17) -0.0005(17) C22 0.061(3) 0.037(3) 0.026(2) 0.0025(19) 0.003(2) -0.003(2) C23 0.056(3) 0.035(3) 0.030(2) 0.003(2) 0.001(2) -0.006(2) C24 0.042(3) 0.033(3) 0.037(3) 0.003(2) 0.000(2) -0.013(2) C25 0.065(4) 0.098(5) 0.051(3) 0.005(3) 0.020(3) -0.017(3) C26 0.090(4) 0.037(3) 0.041(3) 0.008(2) -0.007(3) -0.014(3) C27 0.039(3) 0.031(3) 0.051(3) 0.005(2) 0.006(2) 0.010(2) O1 0.0433(18) 0.0252(16) 0.0288(15) 0.0075(12) 0.0026(13) 0.0042(13) O2 0.052(2) 0.0320(17) 0.0284(16) -0.0058(13) -0.0012(14) -0.0134(15) O3 0.052(2) 0.058(2) 0.063(2) -0.0044(18) 0.0227(18) -0.0139(18) O4 0.0361(17) 0.0282(16) 0.0262(15) -0.0066(12) -0.0069(12) -0.0002(13) O5 0.0312(17) 0.0157(14) 0.0331(15) -0.0003(11) 0.0006(12) -0.0050(12) O6 0.042(2) 0.053(2) 0.090(3) -0.016(2) 0.0005(19) -0.0030(18) O7 0.0438(19) 0.0201(15) 0.0286(15) -0.0015(12) 0.0021(13) -0.0016(13) O8 0.0372(18) 0.0281(16) 0.0313(16) 0.0027(12) -0.0054(13) -0.0023(13) O9 0.066(2) 0.0299(18) 0.055(2) -0.0050(15) 0.0310(18) 0.0053(18) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.382(5) . ? C1 C6 1.392(5) . ? C1 C7 1.530(6) . ? C2 C3 1.379(5) . ? C2 H2 0.9300 . ? C3 C4 1.382(5) . ? C3 C14 1.526(5) . ? C4 C5 1.388(5) . ? C4 H4 0.9300 . ? C5 C6 1.380(5) . ? C5 C21 1.516(5) . ? C6 H6 0.9300 . ? C7 O2 1.411(5) . ? C7 O1 1.421(5) . ? C7 C13 1.509(6) . ? C8 O2 1.415(5) . ? C8 C9 1.531(6) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 C10 1.509(6) . ? C9 C11 1.520(7) . ? C9 C12 1.528(7) . ? C10 O1 1.415(5) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C13 O3 1.376(6) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C14 O4 1.404(5) . ? C14 O5 1.423(5) . ? C14 C20 1.533(6) . ? C15 O5 1.446(5) . ? C15 C16 1.518(6) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 C18 1.515(6) . ? C16 C17 1.517(6) . ? C16 C19 1.522(6) . ? C17 O4 1.419(5) . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? C20 O6 1.426(5) . ? C20 H20A 0.9700 . ? C20 H20B 0.9700 . ? C21 O8 1.412(5) . ? C21 O7 1.414(5) . ? C21 C27 1.522(6) . ? C22 O8 1.431(5) . ? C22 C23 1.514(6) . ? C22 H22A 0.9700 . ? C22 H22B 0.9700 . ? C23 C25 1.519(7) . ? C23 C26 1.525(7) . ? C23 C24 1.529(6) . ? C24 O7 1.419(5) . ? C24 H24A 0.9700 . ? C24 H24B 0.9700 . ? C25 H25A 0.9600 . ? C25 H25B 0.9600 . ? C25 H25C 0.9600 . ? C26 H26A 0.9600 . ? C26 H26B 0.9600 . ? C26 H26C 0.9600 . ? C27 O9 1.409(5) . ? C27 H27A 0.9700 . ? C27 H27B 0.9700 . ? O3 H3 0.8200 . ? O6 H6A 0.8200 . ? O9 H9 0.8200 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C6 118.6(4) . . ? C2 C1 C7 119.5(4) . . ? C6 C1 C7 121.7(3) . . ? C3 C2 C1 121.3(4) . . ? C3 C2 H2 119.3 . . ? C1 C2 H2 119.3 . . ? C2 C3 C4 119.3(4) . . ? C2 C3 C14 120.9(3) . . ? C4 C3 C14 119.4(3) . . ? C3 C4 C5 120.6(4) . . ? C3 C4 H4 119.7 . . ? C5 C4 H4 119.7 . . ? C6 C5 C4 119.2(4) . . ? C6 C5 C21 120.8(3) . . ? C4 C5 C21 119.4(3) . . ? C5 C6 C1 120.9(4) . . ? C5 C6 H6 119.5 . . ? C1 C6 H6 119.5 . . ? O2 C7 O1 111.2(3) . . ? O2 C7 C13 108.1(4) . . ? O1 C7 C13 103.2(3) . . ? O2 C7 C1 111.9(3) . . ? O1 C7 C1 111.3(3) . . ? C13 C7 C1 110.8(3) . . ? O2 C8 C9 112.0(4) . . ? O2 C8 H8A 109.2 . . ? C9 C8 H8A 109.2 . . ? O2 C8 H8B 109.2 . . ? C9 C8 H8B 109.2 . . ? H8A C8 H8B 107.9 . . ? C10 C9 C11 111.4(4) . . ? C10 C9 C12 109.8(4) . . ? C11 C9 C12 110.7(4) . . ? C10 C9 C8 105.1(3) . . ? C11 C9 C8 110.3(4) . . ? C12 C9 C8 109.4(4) . . ? O1 C10 C9 111.7(4) . . ? O1 C10 H10A 109.3 . . ? C9 C10 H10A 109.3 . . ? O1 C10 H10B 109.3 . . ? C9 C10 H10B 109.3 . . ? H10A C10 H10B 107.9 . . ? C9 C11 H11A 109.5 . . ? C9 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C9 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C9 C12 H12A 109.5 . . ? C9 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C9 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? O3 C13 C7 116.0(4) . . ? O3 C13 H13A 108.3 . . ? C7 C13 H13A 108.3 . . ? O3 C13 H13B 108.3 . . ? C7 C13 H13B 108.3 . . ? H13A C13 H13B 107.4 . . ? O4 C14 O5 111.2(3) . . ? O4 C14 C3 112.9(3) . . ? O5 C14 C3 111.3(3) . . ? O4 C14 C20 106.9(3) . . ? O5 C14 C20 103.8(3) . . ? C3 C14 C20 110.3(3) . . ? O5 C15 C16 110.5(3) . . ? O5 C15 H15A 109.5 . . ? C16 C15 H15A 109.5 . . ? O5 C15 H15B 109.5 . . ? C16 C15 H15B 109.5 . . ? H15A C15 H15B 108.1 . . ? C18 C16 C17 111.5(4) . . ? C18 C16 C15 110.7(3) . . ? C17 C16 C15 105.1(3) . . ? C18 C16 C19 111.1(4) . . ? C17 C16 C19 109.6(4) . . ? C15 C16 C19 108.7(4) . . ? O4 C17 C16 111.6(3) . . ? O4 C17 H17A 109.3 . . ? C16 C17 H17A 109.3 . . ? O4 C17 H17B 109.3 . . ? C16 C17 H17B 109.3 . . ? H17A C17 H17B 108.0 . . ? C16 C18 H18A 109.5 . . ? C16 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C16 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C16 C19 H19A 109.5 . . ? C16 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C16 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? O6 C20 C14 112.0(3) . . ? O6 C20 H20A 109.2 . . ? C14 C20 H20A 109.2 . . ? O6 C20 H20B 109.2 . . ? C14 C20 H20B 109.2 . . ? H20A C20 H20B 107.9 . . ? O8 C21 O7 111.5(3) . . ? O8 C21 C5 112.6(3) . . ? O7 C21 C5 113.0(3) . . ? O8 C21 C27 102.8(3) . . ? O7 C21 C27 106.5(3) . . ? C5 C21 C27 109.7(3) . . ? O8 C22 C23 111.1(4) . . ? O8 C22 H22A 109.4 . . ? C23 C22 H22A 109.4 . . ? O8 C22 H22B 109.4 . . ? C23 C22 H22B 109.4 . . ? H22A C22 H22B 108.0 . . ? C22 C23 C25 110.1(4) . . ? C22 C23 C26 111.6(4) . . ? C25 C23 C26 110.9(4) . . ? C22 C23 C24 104.7(3) . . ? C25 C23 C24 109.3(4) . . ? C26 C23 C24 109.9(4) . . ? O7 C24 C23 111.4(4) . . ? O7 C24 H24A 109.4 . . ? C23 C24 H24A 109.4 . . ? O7 C24 H24B 109.4 . . ? C23 C24 H24B 109.4 . . ? H24A C24 H24B 108.0 . . ? C23 C25 H25A 109.5 . . ? C23 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C23 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? C23 C26 H26A 109.5 . . ? C23 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C23 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? O9 C27 C21 112.4(4) . . ? O9 C27 H27A 109.1 . . ? C21 C27 H27A 109.1 . . ? O9 C27 H27B 109.1 . . ? C21 C27 H27B 109.1 . . ? H27A C27 H27B 107.9 . . ? C10 O1 C7 114.4(3) . . ? C7 O2 C8 114.5(3) . . ? C13 O3 H3 109.5 . . ? C14 O4 C17 113.1(3) . . ? C14 O5 C15 113.4(3) . . ? C20 O6 H6A 109.5 . . ? C21 O7 C24 113.4(3) . . ? C21 O8 C22 113.0(3) . . ? C27 O9 H9 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 2.1(6) . . . . ? C7 C1 C2 C3 -174.8(3) . . . . ? C1 C2 C3 C4 -1.7(6) . . . . ? C1 C2 C3 C14 -174.0(3) . . . . ? C2 C3 C4 C5 -0.2(5) . . . . ? C14 C3 C4 C5 172.3(3) . . . . ? C3 C4 C5 C6 1.5(5) . . . . ? C3 C4 C5 C21 -170.0(3) . . . . ? C4 C5 C6 C1 -1.0(6) . . . . ? C21 C5 C6 C1 170.4(3) . . . . ? C2 C1 C6 C5 -0.8(6) . . . . ? C7 C1 C6 C5 176.1(3) . . . . ? C2 C1 C7 O2 -160.9(3) . . . . ? C6 C1 C7 O2 22.2(5) . . . . ? C2 C1 C7 O1 -35.8(5) . . . . ? C6 C1 C7 O1 147.4(4) . . . . ? C2 C1 C7 C13 78.4(5) . . . . ? C6 C1 C7 C13 -98.5(5) . . . . ? O2 C8 C9 C10 -54.8(5) . . . . ? O2 C8 C9 C11 65.3(5) . . . . ? O2 C8 C9 C12 -172.6(4) . . . . ? C11 C9 C10 O1 -64.1(5) . . . . ? C12 C9 C10 O1 172.9(4) . . . . ? C8 C9 C10 O1 55.3(5) . . . . ? O2 C7 C13 O3 -78.1(5) . . . . ? O1 C7 C13 O3 164.1(4) . . . . ? C1 C7 C13 O3 44.8(6) . . . . ? C2 C3 C14 O4 -153.2(3) . . . . ? C4 C3 C14 O4 34.5(5) . . . . ? C2 C3 C14 O5 -27.3(5) . . . . ? C4 C3 C14 O5 160.3(3) . . . . ? C2 C3 C14 C20 87.3(4) . . . . ? C4 C3 C14 C20 -85.1(4) . . . . ? O5 C15 C16 C18 -64.6(4) . . . . ? O5 C15 C16 C17 55.9(4) . . . . ? O5 C15 C16 C19 173.2(3) . . . . ? C18 C16 C17 O4 62.5(4) . . . . ? C15 C16 C17 O4 -57.4(4) . . . . ? C19 C16 C17 O4 -174.0(3) . . . . ? O4 C14 C20 O6 -60.7(4) . . . . ? O5 C14 C20 O6 -178.3(3) . . . . ? C3 C14 C20 O6 62.5(5) . . . . ? C6 C5 C21 O8 154.6(3) . . . . ? C4 C5 C21 O8 -33.9(5) . . . . ? C6 C5 C21 O7 27.2(5) . . . . ? C4 C5 C21 O7 -161.4(3) . . . . ? C6 C5 C21 C27 -91.5(4) . . . . ? C4 C5 C21 C27 80.0(4) . . . . ? O8 C22 C23 C25 174.3(4) . . . . ? O8 C22 C23 C26 -62.0(5) . . . . ? O8 C22 C23 C24 56.9(5) . . . . ? C22 C23 C24 O7 -56.5(5) . . . . ? C25 C23 C24 O7 -174.5(4) . . . . ? C26 C23 C24 O7 63.5(5) . . . . ? O8 C21 C27 O9 176.0(3) . . . . ? O7 C21 C27 O9 -66.6(4) . . . . ? C5 C21 C27 O9 56.0(4) . . . . ? C9 C10 O1 C7 -57.1(5) . . . . ? O2 C7 O1 C10 52.6(4) . . . . ? C13 C7 O1 C10 168.3(3) . . . . ? C1 C7 O1 C10 -72.9(4) . . . . ? O1 C7 O2 C8 -52.0(4) . . . . ? C13 C7 O2 C8 -164.6(3) . . . . ? C1 C7 O2 C8 73.2(4) . . . . ? C9 C8 O2 C7 55.8(5) . . . . ? O5 C14 O4 C17 -55.3(4) . . . . ? C3 C14 O4 C17 70.6(4) . . . . ? C20 C14 O4 C17 -167.9(3) . . . . ? C16 C17 O4 C14 59.1(4) . . . . ? O4 C14 O5 C15 54.6(4) . . . . ? C3 C14 O5 C15 -72.2(4) . . . . ? C20 C14 O5 C15 169.2(3) . . . . ? C16 C15 O5 C14 -57.1(4) . . . . ? O8 C21 O7 C24 -54.4(4) . . . . ? C5 C21 O7 C24 73.6(4) . . . . ? C27 C21 O7 C24 -165.8(3) . . . . ? C23 C24 O7 C21 57.5(4) . . . . ? O7 C21 O8 C22 54.6(4) . . . . ? C5 C21 O8 C22 -73.6(4) . . . . ? C27 C21 O8 C22 168.4(3) . . . . ? C23 C22 O8 C21 -58.5(4) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.538 _refine_diff_density_min -0.333 _refine_diff_density_rms 0.069 # Attachment '832245.cif' data_pv052 _database_code_depnum_ccdc_archive 'CCDC 832245' #TrackingRef '832245.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H20 O3 S3' _chemical_formula_sum 'C18 H20 O3 S3' _chemical_formula_weight 380.52 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' 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 P21/c _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 13.422(3) _cell_length_b 9.1054(16) _cell_length_c 16.551(6) _cell_angle_alpha 90.00 _cell_angle_beta 119.10(2) _cell_angle_gamma 90.00 _cell_volume 1767.4(8) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 5000 _cell_measurement_theta_min 3.3 _cell_measurement_theta_max 52.1 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.430 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 800 _exptl_absorpt_coefficient_mu 0.433 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.8884 _exptl_absorpt_correction_T_max 0.9662 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 'Stoe IPDS 1 diffractometer' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 'no decay' _diffrn_reflns_number 11254 _diffrn_reflns_av_R_equivalents 0.0412 _diffrn_reflns_av_sigmaI/netI 0.0273 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.49 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2968 _reflns_number_gt 2656 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'X-AREA (Stoe & Cie, 2002)' _computing_cell_refinement 'X-AREA (Stoe & Cie, 2002)' _computing_data_reduction 'X-RED (Stoe & Cie, 2002)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'DIAMOND 3 (Brandenburg, 2006)' _computing_publication_material 'enCIFer (CCDC, 2003)' _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^)+(0.0465P)^2^+0.7884P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2968 _refine_ls_number_parameters 230 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0374 _refine_ls_R_factor_gt 0.0330 _refine_ls_wR_factor_ref 0.0832 _refine_ls_wR_factor_gt 0.0815 _refine_ls_goodness_of_fit_ref 1.107 _refine_ls_restrained_S_all 1.107 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.37465(15) 0.40619(18) 0.56808(12) 0.0158(4) Uani 1 1 d . . . C2 C 0.48296(16) 0.32011(19) 0.61717(12) 0.0185(4) Uani 1 1 d . . . H2A H 0.4644 0.2181 0.6204 0.022 Uiso 1 1 calc R . . H2B H 0.5226 0.3245 0.5815 0.022 Uiso 1 1 calc R . . C3 C 0.26643(16) 0.3585(2) 0.53566(12) 0.0197(4) Uani 1 1 d . . . H3A H 0.2479 0.2618 0.5410 0.024 Uiso 1 1 calc R . . C4 C 0.18359(15) 0.47147(19) 0.49246(12) 0.0186(4) Uani 1 1 d . . . H4 H 0.1055 0.4558 0.4666 0.022 Uiso 1 1 calc R . . C5 C 0.23003(14) 0.60451(18) 0.49277(11) 0.0131(4) Uani 1 1 d . . . C6 C 0.17378(14) 0.75565(17) 0.46533(11) 0.0127(4) Uani 1 1 d . . . C7 C 0.24183(14) 0.85462(18) 0.43524(11) 0.0126(4) Uani 1 1 d . . . C8 C 0.32537(14) 0.96859(18) 0.34382(12) 0.0145(4) Uani 1 1 d . . . C9 C 0.35022(16) 1.0119(2) 0.26758(12) 0.0194(4) Uani 1 1 d . . . H9A H 0.3752 0.9263 0.2474 0.023 Uiso 1 1 calc R . . H9B H 0.2811 1.0485 0.2152 0.023 Uiso 1 1 calc R . . C10 C 0.36618(14) 1.02746(18) 0.42969(12) 0.0158(4) Uani 1 1 d . . . H10 H 0.4194 1.1031 0.4521 0.019 Uiso 1 1 calc R . . C11 C 0.31929(15) 0.96168(19) 0.48192(11) 0.0159(4) Uani 1 1 d . . . H11 H 0.3397 0.9893 0.5421 0.019 Uiso 1 1 calc R . . C12 C 0.05412(14) 0.74477(18) 0.38357(11) 0.0130(4) Uani 1 1 d . . . C13 C -0.13720(15) 0.81875(19) 0.25566(12) 0.0159(4) Uani 1 1 d . . . C14 C -0.24785(15) 0.8948(2) 0.19754(13) 0.0195(4) Uani 1 1 d . . . H14A H -0.2343 0.9985 0.1934 0.023 Uiso 1 1 calc R . . H14B H -0.2841 0.8542 0.1355 0.023 Uiso 1 1 calc R . . C15 C -0.09683(15) 0.69341(19) 0.23713(12) 0.0178(4) Uani 1 1 d . . . H15 H -0.1363 0.6411 0.1822 0.021 Uiso 1 1 calc R . . C16 C 0.01138(15) 0.65065(19) 0.30990(12) 0.0166(4) Uani 1 1 d . . . H16 H 0.0496 0.5668 0.3077 0.020 Uiso 1 1 calc R . . C17 C 0.17252(15) 0.82554(19) 0.55101(11) 0.0162(4) Uani 1 1 d . . . H17A H 0.2503 0.8308 0.6015 0.019 Uiso 1 1 calc R . . H17B H 0.1439 0.9252 0.5356 0.019 Uiso 1 1 calc R . . C18 C 0.10037(17) 0.7424(2) 0.58421(13) 0.0232(4) Uani 1 1 d . . . H18A H 0.0228 0.7383 0.5353 0.035 Uiso 1 1 calc R . . H18B H 0.1036 0.7921 0.6366 0.035 Uiso 1 1 calc R . . H18C H 0.1294 0.6444 0.6016 0.035 Uiso 1 1 calc R . . H1 H 0.521(2) 0.372(3) 0.7389(19) 0.040(8) Uiso 1 1 d . . . H2 H 0.404(2) 1.198(3) 0.2897(17) 0.034(7) Uiso 1 1 d . . . H3 H -0.357(2) 0.948(3) 0.2259(16) 0.030(7) Uiso 1 1 d . . . O1 O 0.55745(11) 0.37192(13) 0.70870(9) 0.0169(3) Uani 1 1 d . . . O2 O 0.43602(12) 1.12203(15) 0.29801(9) 0.0205(3) Uani 1 1 d . . . O3 O -0.32177(12) 0.87733(15) 0.23682(10) 0.0237(3) Uani 1 1 d . . . S1 S 0.37677(3) 0.59172(4) 0.54572(3) 0.01487(13) Uani 1 1 d . . . S2 S 0.22646(4) 0.83320(4) 0.32513(3) 0.01589(13) Uani 1 1 d . . . S3 S -0.04068(4) 0.88705(4) 0.36347(3) 0.01577(13) 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 C1 0.0190(9) 0.0132(9) 0.0154(8) 0.0000(6) 0.0084(7) 0.0024(6) C2 0.0187(10) 0.0164(9) 0.0185(9) 0.0000(7) 0.0075(8) 0.0048(7) C3 0.0223(10) 0.0110(9) 0.0259(10) 0.0011(7) 0.0120(8) 0.0006(7) C4 0.0131(9) 0.0154(9) 0.0255(9) 0.0006(7) 0.0080(8) -0.0007(7) C5 0.0120(8) 0.0137(9) 0.0134(8) -0.0004(6) 0.0059(7) 0.0011(6) C6 0.0133(9) 0.0113(8) 0.0136(8) -0.0002(6) 0.0066(7) 0.0012(6) C7 0.0125(8) 0.0110(8) 0.0135(8) 0.0006(6) 0.0057(7) 0.0032(6) C8 0.0125(8) 0.0113(8) 0.0196(8) 0.0013(6) 0.0078(7) 0.0011(6) C9 0.0222(10) 0.0173(9) 0.0210(9) -0.0014(7) 0.0125(8) -0.0034(7) C10 0.0115(8) 0.0130(8) 0.0187(8) 0.0007(6) 0.0039(7) -0.0017(6) C11 0.0155(9) 0.0154(9) 0.0127(8) -0.0018(6) 0.0036(7) -0.0001(6) C12 0.0123(8) 0.0103(8) 0.0180(9) 0.0022(6) 0.0087(7) 0.0017(6) C13 0.0132(9) 0.0169(9) 0.0172(8) 0.0030(7) 0.0071(7) -0.0016(6) C14 0.0150(9) 0.0183(10) 0.0222(9) 0.0053(7) 0.0067(8) 0.0017(7) C15 0.0134(9) 0.0174(9) 0.0204(9) -0.0041(7) 0.0063(7) -0.0035(6) C16 0.0130(9) 0.0124(8) 0.0222(9) -0.0032(7) 0.0069(7) 0.0006(6) C17 0.0195(9) 0.0161(9) 0.0138(8) -0.0010(6) 0.0088(7) 0.0019(6) C18 0.0308(11) 0.0226(10) 0.0217(9) 0.0061(7) 0.0170(9) 0.0066(8) O1 0.0134(6) 0.0179(7) 0.0190(6) 0.0004(5) 0.0075(6) -0.0009(5) O2 0.0198(7) 0.0183(7) 0.0285(7) -0.0005(5) 0.0158(6) -0.0029(5) O3 0.0183(7) 0.0179(7) 0.0379(8) 0.0075(6) 0.0161(6) 0.0075(5) S1 0.0117(2) 0.0132(2) 0.0180(2) 0.00144(15) 0.00589(18) 0.00083(14) S2 0.0206(3) 0.0134(2) 0.0148(2) -0.00387(15) 0.00949(19) -0.00527(15) S3 0.0160(2) 0.0129(2) 0.0165(2) 0.00057(15) 0.00649(18) 0.00494(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 C1 C3 1.352(3) . ? C1 C2 1.496(2) . ? C1 S1 1.7326(17) . ? C2 O1 1.430(2) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 C4 1.426(3) . ? C3 H3A 0.9300 . ? C4 C5 1.361(2) . ? C4 H4 0.9300 . ? C5 C6 1.529(2) . ? C5 S1 1.7267(18) . ? C6 C12 1.519(2) . ? C6 C7 1.529(2) . ? C6 C17 1.562(2) . ? C7 C11 1.359(2) . ? C7 S2 1.7424(18) . ? C8 C10 1.360(3) . ? C8 C9 1.506(3) . ? C8 S2 1.7258(17) . ? C9 O2 1.422(2) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 C11 1.425(3) . ? C10 H10 0.9300 . ? C11 H11 0.9300 . ? C12 C16 1.367(2) . ? C12 S3 1.7309(17) . ? C13 C15 1.361(3) . ? C13 C14 1.490(2) . ? C13 S3 1.7322(18) . ? C14 O3 1.435(3) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C15 C16 1.418(3) . ? C15 H15 0.9300 . ? C16 H16 0.9300 . ? C17 C18 1.527(3) . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? O1 H1 0.85(3) . ? O2 H2 0.79(3) . ? O3 H3 0.77(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 C3 C1 C2 128.29(17) . . ? C3 C1 S1 110.77(13) . . ? C2 C1 S1 120.94(14) . . ? O1 C2 C1 113.36(14) . . ? O1 C2 H2A 108.9 . . ? C1 C2 H2A 108.9 . . ? O1 C2 H2B 108.9 . . ? C1 C2 H2B 108.9 . . ? H2A C2 H2B 107.7 . . ? C1 C3 C4 113.10(16) . . ? C1 C3 H3A 123.5 . . ? C4 C3 H3A 123.5 . . ? C5 C4 C3 113.35(17) . . ? C5 C4 H4 123.3 . . ? C3 C4 H4 123.3 . . ? C4 C5 C6 129.86(16) . . ? C4 C5 S1 110.43(13) . . ? C6 C5 S1 119.22(12) . . ? C12 C6 C7 106.78(13) . . ? C12 C6 C5 111.19(13) . . ? C7 C6 C5 109.91(14) . . ? C12 C6 C17 111.21(15) . . ? C7 C6 C17 109.12(13) . . ? C5 C6 C17 108.60(13) . . ? C11 C7 C6 130.60(16) . . ? C11 C7 S2 110.10(14) . . ? C6 C7 S2 119.28(12) . . ? C10 C8 C9 129.15(16) . . ? C10 C8 S2 110.64(14) . . ? C9 C8 S2 120.10(13) . . ? O2 C9 C8 111.06(14) . . ? O2 C9 H9A 109.4 . . ? C8 C9 H9A 109.4 . . ? O2 C9 H9B 109.4 . . ? C8 C9 H9B 109.4 . . ? H9A C9 H9B 108.0 . . ? C8 C10 C11 113.32(15) . . ? C8 C10 H10 123.3 . . ? C11 C10 H10 123.3 . . ? C7 C11 C10 113.45(16) . . ? C7 C11 H11 123.3 . . ? C10 C11 H11 123.3 . . ? C16 C12 C6 129.69(16) . . ? C16 C12 S3 110.32(13) . . ? C6 C12 S3 118.84(12) . . ? C15 C13 C14 128.70(16) . . ? C15 C13 S3 110.67(13) . . ? C14 C13 S3 120.62(14) . . ? O3 C14 C13 110.34(15) . . ? O3 C14 H14A 109.6 . . ? C13 C14 H14A 109.6 . . ? O3 C14 H14B 109.6 . . ? C13 C14 H14B 109.6 . . ? H14A C14 H14B 108.1 . . ? C13 C15 C16 113.24(16) . . ? C13 C15 H15 123.4 . . ? C16 C15 H15 123.4 . . ? C12 C16 C15 113.42(16) . . ? C12 C16 H16 123.3 . . ? C15 C16 H16 123.3 . . ? C18 C17 C6 114.42(15) . . ? C18 C17 H17A 108.7 . . ? C6 C17 H17A 108.7 . . ? C18 C17 H17B 108.7 . . ? C6 C17 H17B 108.7 . . ? H17A C17 H17B 107.6 . . ? C17 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C17 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C2 O1 H1 108.4(18) . . ? C9 O2 H2 105.9(19) . . ? C14 O3 H3 106.2(19) . . ? C5 S1 C1 92.35(8) . . ? C8 S2 C7 92.47(8) . . ? C12 S3 C13 92.34(8) . . ? 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 C3 C1 C2 O1 -118.5(2) . . . . ? S1 C1 C2 O1 61.6(2) . . . . ? C2 C1 C3 C4 179.85(17) . . . . ? S1 C1 C3 C4 -0.2(2) . . . . ? C1 C3 C4 C5 -0.2(2) . . . . ? C3 C4 C5 C6 -171.34(16) . . . . ? C3 C4 C5 S1 0.4(2) . . . . ? C4 C5 C6 C12 -36.3(3) . . . . ? S1 C5 C6 C12 152.58(13) . . . . ? C4 C5 C6 C7 -154.29(18) . . . . ? S1 C5 C6 C7 34.56(18) . . . . ? C4 C5 C6 C17 86.4(2) . . . . ? S1 C5 C6 C17 -84.75(16) . . . . ? C12 C6 C7 C11 139.24(18) . . . . ? C5 C6 C7 C11 -100.0(2) . . . . ? C17 C6 C7 C11 18.9(2) . . . . ? C12 C6 C7 S2 -42.43(17) . . . . ? C5 C6 C7 S2 78.29(16) . . . . ? C17 C6 C7 S2 -162.73(12) . . . . ? C10 C8 C9 O2 5.7(3) . . . . ? S2 C8 C9 O2 -178.45(12) . . . . ? C9 C8 C10 C11 177.28(16) . . . . ? S2 C8 C10 C11 1.08(19) . . . . ? C6 C7 C11 C10 178.76(16) . . . . ? S2 C7 C11 C10 0.30(19) . . . . ? C8 C10 C11 C7 -0.9(2) . . . . ? C7 C6 C12 C16 86.3(2) . . . . ? C5 C6 C12 C16 -33.6(3) . . . . ? C17 C6 C12 C16 -154.73(18) . . . . ? C7 C6 C12 S3 -80.16(16) . . . . ? C5 C6 C12 S3 159.94(12) . . . . ? C17 C6 C12 S3 38.79(18) . . . . ? C15 C13 C14 O3 108.4(2) . . . . ? S3 C13 C14 O3 -70.57(19) . . . . ? C14 C13 C15 C16 -178.38(18) . . . . ? S3 C13 C15 C16 0.6(2) . . . . ? C6 C12 C16 C15 -166.86(17) . . . . ? S3 C12 C16 C15 0.5(2) . . . . ? C13 C15 C16 C12 -0.8(3) . . . . ? C12 C6 C17 C18 58.59(19) . . . . ? C7 C6 C17 C18 176.13(14) . . . . ? C5 C6 C17 C18 -64.07(19) . . . . ? C4 C5 S1 C1 -0.44(14) . . . . ? C6 C5 S1 C1 172.32(14) . . . . ? C3 C1 S1 C5 0.35(14) . . . . ? C2 C1 S1 C5 -179.67(15) . . . . ? C10 C8 S2 C7 -0.77(14) . . . . ? C9 C8 S2 C7 -177.36(14) . . . . ? C11 C7 S2 C8 0.26(13) . . . . ? C6 C7 S2 C8 -178.40(13) . . . . ? C16 C12 S3 C13 -0.13(14) . . . . ? C6 C12 S3 C13 168.80(14) . . . . ? C15 C13 S3 C12 -0.30(15) . . . . ? C14 C13 S3 C12 178.81(15) . . . . ? _diffrn_measured_fraction_theta_max 0.954 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.954 _refine_diff_density_max 0.440 _refine_diff_density_min -0.281 _refine_diff_density_rms 0.058