# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_vskr #TrackingRef 'polymorph 1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H24 N2 O2' _chemical_formula_weight 336.42 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 'P2(1)/c ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 8.1858(8) _cell_length_b 10.6531(12) _cell_length_c 20.967(2) _cell_angle_alpha 90.00 _cell_angle_beta 92.684(7) _cell_angle_gamma 90.00 _cell_volume 1826.4(3) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 1547 _cell_measurement_theta_min 2.14 _cell_measurement_theta_max 19.86 _exptl_crystal_description needle _exptl_crystal_colour yellow _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.223 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 720 _exptl_absorpt_coefficient_mu 0.079 _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 296(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 15589 _diffrn_reflns_av_R_equivalents 0.0703 _diffrn_reflns_av_sigmaI/netI 0.0751 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 1.94 _diffrn_reflns_theta_max 25.50 _reflns_number_total 3387 _reflns_number_gt 1697 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0182P)^2^+0.7000P] 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 3387 _refine_ls_number_parameters 237 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1232 _refine_ls_R_factor_gt 0.0536 _refine_ls_wR_factor_ref 0.1071 _refine_ls_wR_factor_gt 0.0896 _refine_ls_goodness_of_fit_ref 1.049 _refine_ls_restrained_S_all 1.049 _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 C4 C 0.4832(3) 0.3794(2) 0.88075(11) 0.0413(6) Uani 1 1 d . . . C5 C 0.4155(3) 0.4973(2) 0.87092(12) 0.0488(7) Uani 1 1 d . . . H5 H 0.4383 0.5600 0.9009 0.059 Uiso 1 1 calc R . . C3 C 0.4457(3) 0.2864(3) 0.83631(12) 0.0487(7) Uani 1 1 d . . . H3 H 0.4898 0.2067 0.8427 0.058 Uiso 1 1 calc R . . C2 C 0.3440(3) 0.3085(3) 0.78223(12) 0.0499(7) Uani 1 1 d . . . C1 C 0.2811(3) 0.4294(3) 0.77368(13) 0.0517(8) Uani 1 1 d . . . C6 C 0.3136(3) 0.5252(3) 0.81713(14) 0.0535(7) Uani 1 1 d . . . C7 C 0.3046(4) 0.2059(3) 0.73442(13) 0.0754(10) Uani 1 1 d . . . H7A H 0.3546 0.1289 0.7490 0.113 Uiso 1 1 calc R . . H7B H 0.3458 0.2285 0.6939 0.113 Uiso 1 1 calc R . . H7C H 0.1882 0.1949 0.7300 0.113 Uiso 1 1 calc R . . C8 C 0.2460(4) 0.6556(3) 0.80517(15) 0.0793(10) Uani 1 1 d . . . H8A H 0.2954 0.6915 0.7688 0.119 Uiso 1 1 calc R . . H8B H 0.2698 0.7071 0.8420 0.119 Uiso 1 1 calc R . . H8C H 0.1297 0.6508 0.7971 0.119 Uiso 1 1 calc R . . C16 C 0.5923(3) 0.1098(2) 1.07270(11) 0.0424(6) Uani 1 1 d . . . C19 C 0.3733(3) 0.2376(2) 0.99150(11) 0.0445(7) Uani 1 1 d . . . H19 H 0.2994 0.2807 0.9645 0.053 Uiso 1 1 calc R . . C14 C 0.5391(3) 0.2583(2) 0.98591(11) 0.0390(6) Uani 1 1 d . . . C9 C 0.6018(3) 0.3539(2) 0.93819(11) 0.0410(6) Uani 1 1 d . . . H9 H 0.6154 0.4335 0.9612 0.049 Uiso 1 1 calc R . . C15 C 0.6462(3) 0.1939(2) 1.02737(11) 0.0451(7) Uani 1 1 d . . . H15 H 0.7580 0.2073 1.0248 0.054 Uiso 1 1 calc R . . C18 C 0.3130(3) 0.1545(2) 1.03612(12) 0.0426(7) Uani 1 1 d . . . C17 C 0.4256(3) 0.0910(2) 1.07615(11) 0.0412(6) Uani 1 1 d . . . C21 C 0.1319(3) 0.1333(3) 1.04153(13) 0.0622(8) Uani 1 1 d . . . H21A H 0.1071 0.0463 1.0342 0.093 Uiso 1 1 calc R . . H21B H 0.0725 0.1836 1.0103 0.093 Uiso 1 1 calc R . . H21C H 0.1009 0.1566 1.0835 0.093 Uiso 1 1 calc R . . C20 C 0.7126(3) 0.0394(3) 1.11641(13) 0.0614(8) Uani 1 1 d . . . H20A H 0.6858 0.0524 1.1600 0.092 Uiso 1 1 calc R . . H20B H 0.8212 0.0697 1.1103 0.092 Uiso 1 1 calc R . . H20C H 0.7073 -0.0486 1.1067 0.092 Uiso 1 1 calc R . . C10 C 0.7674(3) 0.3199(2) 0.91451(11) 0.0421(6) Uani 1 1 d . . . C12 C 0.9490(3) 0.2071(3) 0.87054(13) 0.0553(8) Uani 1 1 d . . . H12 H 1.0035 0.1401 0.8526 0.066 Uiso 1 1 calc R . . C11 C 0.8946(3) 0.3984(3) 0.90410(12) 0.0491(7) Uani 1 1 d . . . C13 C 0.9193(3) 0.5353(3) 0.91498(15) 0.0749(10) Uani 1 1 d . . . H13A H 0.8387 0.5658 0.9430 0.112 Uiso 1 1 calc R . . H13B H 0.9084 0.5788 0.8749 0.112 Uiso 1 1 calc R . . H13C H 1.0266 0.5495 0.9340 0.112 Uiso 1 1 calc R . . N2 N 0.8029(3) 0.1993(2) 0.89401(10) 0.0487(6) Uani 1 1 d . . . N1 N 1.0094(3) 0.3243(2) 0.87573(11) 0.0560(7) Uani 1 1 d . . . O2 O 0.3728(2) 0.01008(17) 1.12285(8) 0.0537(5) Uani 1 1 d . . . H2 H 0.3151 -0.0448 1.1061 0.081 Uiso 1 1 calc R . . O1 O 0.1755(2) 0.4539(2) 0.72117(9) 0.0720(6) Uani 1 1 d . . . H1 H 0.2228 0.4405 0.6882 0.108 Uiso 1 1 calc R . . H1M H 1.108(4) 0.349(3) 0.8634(14) 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 C4 0.0440(16) 0.0433(17) 0.0373(15) 0.0054(14) 0.0082(12) -0.0010(13) C5 0.0532(18) 0.0488(18) 0.0450(17) 0.0042(14) 0.0073(14) 0.0018(14) C3 0.0485(17) 0.0504(18) 0.0478(17) 0.0030(15) 0.0081(14) 0.0051(14) C2 0.0463(17) 0.067(2) 0.0372(16) -0.0006(16) 0.0062(13) -0.0031(15) C1 0.0409(17) 0.074(2) 0.0409(16) 0.0200(17) 0.0088(13) 0.0013(15) C6 0.0534(18) 0.0527(19) 0.0550(19) 0.0109(16) 0.0092(15) 0.0011(15) C7 0.075(2) 0.094(3) 0.0570(19) -0.0143(19) -0.0043(16) 0.0037(19) C8 0.091(2) 0.061(2) 0.085(2) 0.0184(19) -0.0019(19) 0.0142(18) C16 0.0453(17) 0.0423(16) 0.0398(15) 0.0041(13) 0.0051(12) 0.0032(13) C19 0.0422(17) 0.0519(17) 0.0391(15) 0.0016(14) 0.0000(12) 0.0030(13) C14 0.0369(16) 0.0448(16) 0.0359(14) 0.0021(13) 0.0074(12) 0.0005(12) C9 0.0413(16) 0.0435(16) 0.0386(15) 0.0004(13) 0.0058(12) -0.0005(12) C15 0.0363(15) 0.0545(17) 0.0448(16) -0.0003(15) 0.0052(13) -0.0006(13) C18 0.0380(16) 0.0519(17) 0.0385(15) -0.0029(14) 0.0071(12) -0.0040(13) C17 0.0491(17) 0.0420(16) 0.0335(14) -0.0042(13) 0.0104(12) -0.0051(13) C21 0.0446(17) 0.075(2) 0.067(2) 0.0091(17) 0.0060(14) -0.0078(16) C20 0.0544(18) 0.063(2) 0.066(2) 0.0156(17) 0.0002(15) 0.0031(15) C10 0.0407(16) 0.0447(17) 0.0410(15) 0.0056(14) 0.0031(12) -0.0035(13) C12 0.0531(19) 0.056(2) 0.0575(19) 0.0050(16) 0.0126(15) 0.0046(16) C11 0.0495(18) 0.0505(18) 0.0478(17) 0.0077(15) 0.0057(14) -0.0021(15) C13 0.070(2) 0.064(2) 0.092(3) 0.0090(19) 0.0095(18) -0.0157(18) N2 0.0422(14) 0.0500(15) 0.0550(14) 0.0017(12) 0.0128(11) 0.0004(11) N1 0.0430(16) 0.0666(19) 0.0595(16) 0.0117(14) 0.0149(13) -0.0053(14) O2 0.0621(13) 0.0548(13) 0.0446(11) 0.0051(10) 0.0075(9) -0.0134(9) O1 0.0582(13) 0.1101(18) 0.0477(12) 0.0220(14) 0.0021(10) 0.0078(12) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C4 C5 1.384(3) . ? C4 C3 1.384(3) . ? C4 C9 1.535(3) . ? C5 C6 1.403(3) . ? C3 C2 1.395(3) . ? C2 C1 1.396(4) . ? C2 C7 1.508(3) . ? C1 C6 1.386(4) . ? C1 O1 1.392(3) . ? C6 C8 1.512(4) . ? C16 C17 1.385(3) . ? C16 C15 1.393(3) . ? C16 C20 1.512(3) . ? C19 C14 1.386(3) . ? C19 C18 1.395(3) . ? C14 C15 1.387(3) . ? C14 C9 1.532(3) . ? C9 C10 1.509(3) . ? C18 C17 1.392(3) . ? C18 C21 1.509(3) . ? C17 O2 1.389(3) . ? C10 C11 1.361(3) . ? C10 N2 1.390(3) . ? C12 N2 1.317(3) . ? C12 N1 1.346(3) . ? C11 N1 1.383(3) . ? C11 C13 1.488(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 C5 C4 C3 118.3(2) . . ? C5 C4 C9 120.8(2) . . ? C3 C4 C9 120.9(2) . . ? C4 C5 C6 122.1(3) . . ? C4 C3 C2 122.1(3) . . ? C3 C2 C1 117.6(3) . . ? C3 C2 C7 121.3(3) . . ? C1 C2 C7 121.1(2) . . ? C6 C1 O1 118.4(3) . . ? C6 C1 C2 122.5(2) . . ? O1 C1 C2 119.1(3) . . ? C1 C6 C5 117.5(3) . . ? C1 C6 C8 120.7(3) . . ? C5 C6 C8 121.8(3) . . ? C17 C16 C15 118.2(2) . . ? C17 C16 C20 120.8(2) . . ? C15 C16 C20 120.9(2) . . ? C14 C19 C18 122.4(2) . . ? C19 C14 C15 117.5(2) . . ? C19 C14 C9 121.3(2) . . ? C15 C14 C9 121.1(2) . . ? C10 C9 C14 112.9(2) . . ? C10 C9 C4 109.19(19) . . ? C14 C9 C4 114.3(2) . . ? C14 C15 C16 122.3(2) . . ? C17 C18 C19 117.9(2) . . ? C17 C18 C21 120.4(2) . . ? C19 C18 C21 121.6(2) . . ? C16 C17 O2 117.8(2) . . ? C16 C17 C18 121.6(2) . . ? O2 C17 C18 120.5(2) . . ? C11 C10 N2 110.2(2) . . ? C11 C10 C9 127.7(2) . . ? N2 C10 C9 121.8(2) . . ? N2 C12 N1 111.4(3) . . ? C10 C11 N1 105.0(2) . . ? C10 C11 C13 132.6(3) . . ? N1 C11 C13 122.3(3) . . ? C12 N2 C10 105.3(2) . . ? C12 N1 C11 108.0(2) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.229 _refine_diff_density_min -0.223 _refine_diff_density_rms 0.045 _database_code_depnum_ccdc_archive 'CCDC 904126' ####################################################################### # # 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_vskr_1 #TrackingRef 'polymorph 2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H24 N2 O2' _chemical_formula_weight 336.42 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 'C2/c ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 21.5904(13) _cell_length_b 13.6380(8) _cell_length_c 16.9958(17) _cell_angle_alpha 90.00 _cell_angle_beta 123.947(3) _cell_angle_gamma 90.00 _cell_volume 4151.4(5) _cell_formula_units_Z 8 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.33 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.077 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1440 _exptl_absorpt_coefficient_mu 0.070 _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 296(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 21599 _diffrn_reflns_av_R_equivalents 0.0868 _diffrn_reflns_av_sigmaI/netI 0.0825 _diffrn_reflns_limit_h_min -26 _diffrn_reflns_limit_h_max 26 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.88 _diffrn_reflns_theta_max 25.50 _reflns_number_total 3865 _reflns_number_gt 1799 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0001P)^2^+40.0200P] 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 3865 _refine_ls_number_parameters 237 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1690 _refine_ls_R_factor_gt 0.0818 _refine_ls_wR_factor_ref 0.2355 _refine_ls_wR_factor_gt 0.1977 _refine_ls_goodness_of_fit_ref 0.997 _refine_ls_restrained_S_all 0.997 _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 C4 C 0.8964(3) 0.1899(4) -0.0163(4) 0.0490(15) Uani 1 1 d . . . C3 C 0.8525(3) 0.2221(4) -0.1101(4) 0.0523(15) Uani 1 1 d . . . H3 H 0.8450 0.2890 -0.1223 0.063 Uiso 1 1 calc R . . C2 C 0.8198(3) 0.1568(5) -0.1859(4) 0.0587(17) Uani 1 1 d . . . C5 C 0.9077(3) 0.0897(5) -0.0004(5) 0.0627(18) Uani 1 1 d . . . H5 H 0.9376 0.0670 0.0617 0.075 Uiso 1 1 calc R . . C6 C 0.8755(4) 0.0221(5) -0.0745(5) 0.074(2) Uani 1 1 d . . . C1 C 0.8320(3) 0.0572(5) -0.1661(5) 0.069(2) Uani 1 1 d . . . C7 C 0.7734(4) 0.1960(6) -0.2856(4) 0.079(2) Uani 1 1 d . . . H7A H 0.7779 0.2661 -0.2844 0.118 Uiso 1 1 calc R . . H7B H 0.7221 0.1786 -0.3141 0.118 Uiso 1 1 calc R . . H7C H 0.7907 0.1685 -0.3220 0.118 Uiso 1 1 calc R . . C8 C 0.8881(5) -0.0865(5) -0.0550(7) 0.130(4) Uani 1 1 d . . . H8A H 0.8413 -0.1181 -0.0771 0.196 Uiso 1 1 calc R . . H8B H 0.9218 -0.0971 0.0120 0.196 Uiso 1 1 calc R . . H8C H 0.9090 -0.1134 -0.0873 0.196 Uiso 1 1 calc R . . C17 C 1.1013(3) 0.4540(4) 0.0978(4) 0.0442(14) Uani 1 1 d . . . C15 C 1.0182(3) 0.4047(4) 0.1409(4) 0.0460(14) Uani 1 1 d . . . H15 H 0.9996 0.4129 0.1784 0.055 Uiso 1 1 calc R . . C18 C 1.0729(3) 0.3815(4) 0.0285(4) 0.0444(14) Uani 1 1 d . . . C9 C 0.9304(3) 0.2610(4) 0.0671(4) 0.0484(15) Uani 1 1 d . . . H9 H 0.9573 0.2204 0.1244 0.058 Uiso 1 1 calc R . . C19 C 1.0162(3) 0.3208(4) 0.0174(4) 0.0447(14) Uani 1 1 d . . . H19 H 0.9966 0.2723 -0.0289 0.054 Uiso 1 1 calc R . . C16 C 1.0742(3) 0.4667(4) 0.1550(4) 0.0448(14) Uani 1 1 d . . . C14 C 0.9885(3) 0.3310(4) 0.0734(3) 0.0418(13) Uani 1 1 d . . . C21 C 1.1018(4) 0.3667(5) -0.0336(4) 0.0637(18) Uani 1 1 d . . . H21A H 1.0916 0.4241 -0.0717 0.095 Uiso 1 1 calc R . . H21B H 1.0775 0.3110 -0.0741 0.095 Uiso 1 1 calc R . . H21C H 1.1547 0.3555 0.0055 0.095 Uiso 1 1 calc R . . C20 C 1.1045(4) 0.5466(5) 0.2289(4) 0.0640(18) Uani 1 1 d . . . H20A H 1.0907 0.6094 0.1981 0.096 Uiso 1 1 calc R . . H20B H 1.1579 0.5417 0.2692 0.096 Uiso 1 1 calc R . . H20C H 1.0840 0.5396 0.2663 0.096 Uiso 1 1 calc R . . C10 C 0.8704(3) 0.3137(4) 0.0706(4) 0.0462(14) Uani 1 1 d . . . C11 C 0.8405(4) 0.2892(5) 0.1212(4) 0.0569(17) Uani 1 1 d . . . C12 C 0.7825(4) 0.4174(5) 0.0313(5) 0.0652(18) Uani 1 1 d . . . H12 H 0.7489 0.4690 0.0026 0.078 Uiso 1 1 calc R . . C13 C 0.8591(4) 0.2100(5) 0.1916(5) 0.081(2) Uani 1 1 d . . . H13A H 0.8741 0.2387 0.2513 0.121 Uiso 1 1 calc R . . H13B H 0.8991 0.1708 0.1995 0.121 Uiso 1 1 calc R . . H13C H 0.8160 0.1694 0.1693 0.121 Uiso 1 1 calc R . . O2 O 1.1599(2) 0.5132(3) 0.1158(3) 0.0521(11) Uani 1 1 d . . . H2 H 1.1530 0.5310 0.0654 0.078 Uiso 1 1 calc R . . O1 O 0.8033(3) -0.0115(4) -0.2376(4) 0.105(2) Uani 1 1 d . . . H1 H 0.7592 0.0006 -0.2774 0.158 Uiso 1 1 calc R . . N2 N 0.8339(3) 0.3946(4) 0.0148(3) 0.0535(13) Uani 1 1 d . . . N1 N 0.7853(3) 0.3566(5) 0.0944(4) 0.0672(16) Uani 1 1 d D . . H1M H 0.759(3) 0.360(5) 0.118(4) 0.09(3) Uiso 1 1 d 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 C4 0.043(3) 0.048(4) 0.052(3) -0.005(3) 0.024(3) -0.009(3) C3 0.051(4) 0.049(4) 0.050(3) -0.007(3) 0.024(3) -0.010(3) C2 0.044(4) 0.073(5) 0.051(4) -0.013(3) 0.022(3) -0.009(3) C5 0.052(4) 0.049(4) 0.063(4) 0.003(3) 0.017(3) 0.001(3) C6 0.051(4) 0.047(4) 0.088(5) -0.015(4) 0.017(4) 0.001(3) C1 0.044(4) 0.066(5) 0.072(5) -0.031(4) 0.017(4) 0.003(3) C7 0.073(5) 0.091(6) 0.055(4) -0.016(4) 0.024(4) -0.013(4) C8 0.116(8) 0.046(5) 0.132(8) -0.013(5) 0.010(6) 0.016(5) C17 0.033(3) 0.044(3) 0.039(3) 0.006(3) 0.010(2) -0.002(3) C15 0.048(3) 0.049(3) 0.040(3) 0.000(3) 0.025(3) -0.006(3) C18 0.039(3) 0.046(3) 0.042(3) 0.009(3) 0.018(3) 0.003(3) C9 0.050(3) 0.045(3) 0.040(3) 0.002(3) 0.020(3) -0.011(3) C19 0.045(3) 0.042(3) 0.036(3) 0.001(3) 0.016(3) 0.001(3) C16 0.046(3) 0.041(3) 0.037(3) 0.002(3) 0.017(3) -0.004(3) C14 0.039(3) 0.042(3) 0.033(3) 0.003(2) 0.013(2) -0.002(3) C21 0.065(4) 0.069(4) 0.059(4) -0.005(3) 0.036(4) -0.007(4) C20 0.068(4) 0.066(4) 0.053(4) -0.013(3) 0.031(3) -0.020(4) C10 0.047(3) 0.051(4) 0.037(3) -0.007(3) 0.021(3) -0.018(3) C11 0.061(4) 0.063(4) 0.045(3) -0.006(3) 0.029(3) -0.021(4) C12 0.058(4) 0.064(5) 0.072(5) -0.003(4) 0.036(4) -0.009(4) C13 0.097(6) 0.085(5) 0.064(4) 0.005(4) 0.047(4) -0.029(5) O2 0.042(2) 0.058(3) 0.045(2) 0.005(2) 0.0167(19) -0.012(2) O1 0.061(3) 0.093(4) 0.099(4) -0.057(3) 0.006(3) 0.015(3) N2 0.051(3) 0.054(3) 0.054(3) 0.003(3) 0.029(3) -0.005(3) N1 0.067(4) 0.080(4) 0.068(4) -0.014(3) 0.046(3) -0.022(4) _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 C4 C5 1.387(8) . ? C4 C3 1.395(8) . ? C4 C9 1.525(8) . ? C3 C2 1.391(8) . ? C2 C1 1.390(9) . ? C2 C7 1.505(8) . ? C5 C6 1.394(9) . ? C6 C1 1.379(10) . ? C6 C8 1.509(9) . ? C1 O1 1.378(7) . ? C17 O2 1.383(6) . ? C17 C18 1.390(7) . ? C17 C16 1.398(8) . ? C15 C16 1.382(7) . ? C15 C14 1.384(7) . ? C18 C19 1.400(7) . ? C18 C21 1.511(8) . ? C9 C10 1.511(8) . ? C9 C14 1.532(7) . ? C19 C14 1.386(7) . ? C16 C20 1.507(8) . ? C10 C11 1.375(8) . ? C10 N2 1.379(7) . ? C11 N1 1.365(9) . ? C11 C13 1.492(8) . ? C12 N2 1.325(8) . ? C12 N1 1.330(8) . ? 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 C5 C4 C3 117.8(6) . . ? C5 C4 C9 120.3(5) . . ? C3 C4 C9 121.9(5) . . ? C2 C3 C4 121.8(6) . . ? C1 C2 C3 118.1(6) . . ? C1 C2 C7 122.5(6) . . ? C3 C2 C7 119.4(6) . . ? C4 C5 C6 122.1(6) . . ? C1 C6 C5 118.2(6) . . ? C1 C6 C8 121.0(7) . . ? C5 C6 C8 120.9(7) . . ? O1 C1 C6 116.6(7) . . ? O1 C1 C2 121.3(7) . . ? C6 C1 C2 122.0(6) . . ? O2 C17 C18 121.2(5) . . ? O2 C17 C16 117.4(5) . . ? C18 C17 C16 121.3(5) . . ? C16 C15 C14 123.0(5) . . ? C17 C18 C19 118.2(5) . . ? C17 C18 C21 121.9(5) . . ? C19 C18 C21 119.9(5) . . ? C10 C9 C4 111.1(5) . . ? C10 C9 C14 112.8(5) . . ? C4 C9 C14 114.4(5) . . ? C14 C19 C18 121.9(5) . . ? C15 C16 C17 117.9(5) . . ? C15 C16 C20 121.2(5) . . ? C17 C16 C20 120.9(5) . . ? C15 C14 C19 117.6(5) . . ? C15 C14 C9 119.6(5) . . ? C19 C14 C9 122.7(5) . . ? C11 C10 N2 109.6(6) . . ? C11 C10 C9 128.5(6) . . ? N2 C10 C9 121.8(5) . . ? N1 C11 C10 104.8(6) . . ? N1 C11 C13 123.3(6) . . ? C10 C11 C13 131.9(7) . . ? N2 C12 N1 111.0(6) . . ? C12 N2 C10 105.5(5) . . ? C12 N1 C11 109.1(6) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.788 _refine_diff_density_min -0.199 _refine_diff_density_rms 0.080 _database_code_depnum_ccdc_archive 'CCDC 904127' ####################################################################### # # 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_123a #TrackingRef 'acetone.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C45 H54 N4 O5' _chemical_formula_weight 730.92 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 'C2/c ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 21.9667(7) _cell_length_b 13.4559(7) _cell_length_c 17.1405(7) _cell_angle_alpha 90.00 _cell_angle_beta 124.165(4) _cell_angle_gamma 90.00 _cell_volume 4192.1(3) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description needle _exptl_crystal_colour yellow _exptl_crystal_size_max 0.33 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.158 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1568 _exptl_absorpt_coefficient_mu 0.076 _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 296(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 27058 _diffrn_reflns_av_R_equivalents 0.0290 _diffrn_reflns_av_sigmaI/netI 0.0236 _diffrn_reflns_limit_h_min -26 _diffrn_reflns_limit_h_max 26 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.88 _diffrn_reflns_theta_max 25.50 _reflns_number_total 3902 _reflns_number_gt 2766 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0000P)^2^+10.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3902 _refine_ls_number_parameters 257 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0929 _refine_ls_R_factor_gt 0.0689 _refine_ls_wR_factor_ref 0.1273 _refine_ls_wR_factor_gt 0.1199 _refine_ls_goodness_of_fit_ref 1.076 _refine_ls_restrained_S_all 1.079 _refine_ls_shift/su_max 0.007 _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 1.09835(14) 0.5469(2) 0.09612(19) 0.0481(7) Uani 1 1 d . . . C5 C 1.01326(14) 0.6804(2) 0.01664(19) 0.0490(7) Uani 1 1 d . . . H5 H 0.9932 0.7296 -0.0294 0.059 Uiso 1 1 calc R . . C3 C 1.01727(15) 0.5945(2) 0.14041(19) 0.0512(7) Uani 1 1 d . . . H3 H 0.9992 0.5860 0.1778 0.061 Uiso 1 1 calc R . . C4 C 0.98738(14) 0.6688(2) 0.07273(18) 0.0451(6) Uani 1 1 d . . . C6 C 1.06970(15) 0.6192(2) 0.02764(19) 0.0503(7) Uani 1 1 d . . . C2 C 1.07270(14) 0.5325(2) 0.15453(19) 0.0492(7) Uani 1 1 d . . . C8 C 1.09745(18) 0.6353(3) -0.0340(2) 0.0695(9) Uani 1 1 d . . . H8A H 1.1496 0.6463 0.0047 0.104 Uiso 1 1 calc R . . H8B H 1.0735 0.6923 -0.0735 0.104 Uiso 1 1 calc R . . H8C H 1.0869 0.5777 -0.0727 0.104 Uiso 1 1 calc R . . C7 C 1.10327(18) 0.4519(2) 0.2270(2) 0.0708(9) Uani 1 1 d . . . H7A H 1.0824 0.4569 0.2633 0.106 Uiso 1 1 calc R . . H7B H 1.1558 0.4587 0.2680 0.106 Uiso 1 1 calc R . . H7C H 1.0913 0.3884 0.1963 0.106 Uiso 1 1 calc R . . C9 C 0.92890(15) 0.7394(2) 0.0664(2) 0.0511(7) Uani 1 1 d . . . H9 H 0.9552 0.7812 0.1230 0.061 Uiso 1 1 calc R . . C16 C 0.81437(16) 0.8433(2) -0.1858(2) 0.0567(8) Uani 1 1 d . . . C14 C 0.89449(15) 0.8102(2) -0.0172(2) 0.0525(7) Uani 1 1 d . . . C15 C 0.84892(15) 0.7772(2) -0.1104(2) 0.0541(7) Uani 1 1 d . . . H15 H 0.8415 0.7094 -0.1224 0.065 Uiso 1 1 calc R . . C17 C 0.82734(16) 0.9432(2) -0.1664(2) 0.0624(8) Uani 1 1 d . . . C19 C 0.90640(17) 0.9108(2) -0.0021(2) 0.0683(9) Uani 1 1 d . . . H19 H 0.9377 0.9340 0.0593 0.082 Uiso 1 1 calc R . . C18 C 0.87272(18) 0.9798(2) -0.0765(3) 0.0758(10) Uani 1 1 d . . . C20 C 0.76598(19) 0.8034(3) -0.2842(2) 0.0833(11) Uani 1 1 d . . . H20A H 0.7157 0.8208 -0.3098 0.125 Uiso 1 1 calc R . . H20B H 0.7706 0.7324 -0.2830 0.125 Uiso 1 1 calc R . . H20C H 0.7806 0.8315 -0.3227 0.125 Uiso 1 1 calc R . . C21 C 0.8868(3) 1.0895(3) -0.0589(3) 0.141(2) Uani 1 1 d . . . H21A H 0.8915 1.1183 -0.1065 0.211 Uiso 1 1 calc R . . H21B H 0.9313 1.1002 0.0020 0.211 Uiso 1 1 calc R . . H21C H 0.8464 1.1202 -0.0611 0.211 Uiso 1 1 calc R . . C10 C 0.87073(15) 0.6858(2) 0.07025(19) 0.0506(7) Uani 1 1 d . . . O1 O 1.15618(10) 0.48788(16) 0.11384(13) 0.0569(5) Uani 1 1 d . . . H1 H 1.1514 0.4745 0.0640 0.085 Uiso 1 1 calc R . . O2 O 0.79612(13) 1.01460(19) -0.23716(19) 0.0978(9) Uani 1 1 d . . . H2 H 0.7564 0.9945 -0.2820 0.147 Uiso 1 1 calc R . . C23 C 0.0612(5) 0.1214(9) 0.2603(9) 0.372(8) Uani 1 1 d . . . H23A H 0.1015 0.1217 0.3254 0.559 Uiso 1 1 calc R . . H23B H 0.0471 0.1886 0.2386 0.559 Uiso 1 1 calc R . . H23C H 0.0759 0.0887 0.2236 0.559 Uiso 1 1 calc R . . O3 O 0.0000 -0.0256(9) 0.2500 0.367(8) Uani 1 2 d SD . . C22 C 0.0000 0.0696(10) 0.2500 0.174(4) Uani 1 2 d SD . . N2 N 0.83467(13) 0.60230(19) 0.01497(18) 0.0580(6) Uani 1 1 d . . . N1 N 0.78595(16) 0.6422(2) 0.0930(2) 0.0696(8) Uani 1 1 d . . . C12 C 0.78390(17) 0.5796(3) 0.0308(2) 0.0683(9) Uani 1 1 d . . . H12 H 0.7510 0.5270 0.0024 0.082 Uiso 1 1 calc R . . C11 C 0.84100(17) 0.7110(2) 0.1194(2) 0.0593(8) Uani 1 1 d . . . C13 C 0.8579(2) 0.7916(3) 0.1882(2) 0.0809(11) Uani 1 1 d . . . H13A H 0.8805 0.7636 0.2500 0.121 Uiso 1 1 calc R . . H13B H 0.8132 0.8248 0.1705 0.121 Uiso 1 1 calc R . . H13C H 0.8910 0.8384 0.1883 0.121 Uiso 1 1 calc R . . H1M H 0.747(2) 0.644(3) 0.106(3) 0.126(15) 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 0.0353(14) 0.0518(17) 0.0459(16) -0.0113(13) 0.0158(13) 0.0011(12) C5 0.0453(15) 0.0502(17) 0.0451(16) 0.0003(13) 0.0215(13) -0.0022(13) C3 0.0523(17) 0.0569(18) 0.0456(16) -0.0009(14) 0.0282(14) 0.0031(14) C4 0.0474(15) 0.0419(15) 0.0420(15) -0.0022(12) 0.0226(13) 0.0028(12) C6 0.0453(15) 0.0558(18) 0.0508(17) -0.0092(14) 0.0276(14) -0.0047(14) C2 0.0433(15) 0.0492(17) 0.0495(16) -0.0050(13) 0.0226(14) 0.0034(13) C8 0.069(2) 0.069(2) 0.072(2) 0.0072(18) 0.0404(19) 0.0063(17) C7 0.072(2) 0.073(2) 0.064(2) 0.0138(17) 0.0358(18) 0.0204(18) C9 0.0526(17) 0.0501(17) 0.0475(16) -0.0020(13) 0.0263(14) 0.0062(14) C16 0.0496(17) 0.064(2) 0.0600(19) 0.0070(16) 0.0328(15) 0.0034(15) C14 0.0484(16) 0.0478(17) 0.0603(18) 0.0048(14) 0.0299(15) 0.0077(13) C15 0.0519(17) 0.0514(17) 0.0554(18) 0.0077(14) 0.0279(15) 0.0108(14) C17 0.0465(17) 0.061(2) 0.069(2) 0.0204(17) 0.0259(16) -0.0017(15) C19 0.062(2) 0.0509(19) 0.072(2) -0.0028(17) 0.0251(17) -0.0043(16) C18 0.061(2) 0.0482(19) 0.084(3) 0.0071(18) 0.0198(19) -0.0057(16) C20 0.077(2) 0.088(3) 0.069(2) 0.010(2) 0.032(2) 0.008(2) C21 0.138(4) 0.053(2) 0.129(4) 0.012(3) 0.012(3) -0.021(3) C10 0.0501(16) 0.0542(18) 0.0490(16) 0.0052(14) 0.0288(14) 0.0147(14) O1 0.0445(11) 0.0664(13) 0.0526(12) -0.0091(11) 0.0229(10) 0.0108(10) O2 0.0672(16) 0.0784(17) 0.097(2) 0.0409(15) 0.0155(14) -0.0131(13) C23 0.287(13) 0.413(18) 0.57(2) -0.077(16) 0.330(15) -0.124(12) O3 0.437(19) 0.199(10) 0.402(17) 0.000 0.197(14) 0.000 C22 0.150(9) 0.254(14) 0.134(7) 0.000 0.089(7) 0.000 N2 0.0537(14) 0.0603(16) 0.0664(16) -0.0020(13) 0.0376(13) 0.0029(12) N1 0.0663(18) 0.081(2) 0.0802(19) 0.0082(16) 0.0523(17) 0.0144(16) C12 0.059(2) 0.072(2) 0.080(2) 0.0027(19) 0.0431(19) 0.0047(17) C11 0.0642(19) 0.062(2) 0.0562(18) 0.0087(15) 0.0367(17) 0.0196(16) C13 0.097(3) 0.084(3) 0.074(2) -0.006(2) 0.056(2) 0.022(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C6 1.374(4) . ? C1 O1 1.380(3) . ? C1 C2 1.411(4) . ? C5 C4 1.373(4) . ? C5 C6 1.411(4) . ? C3 C2 1.380(4) . ? C3 C4 1.386(4) . ? C4 C9 1.552(4) . ? C6 C8 1.504(4) . ? C2 C7 1.495(4) . ? C9 C10 1.500(4) . ? C9 C14 1.522(4) . ? C16 C17 1.375(4) . ? C16 C15 1.390(4) . ? C16 C20 1.500(4) . ? C14 C19 1.376(4) . ? C14 C15 1.398(4) . ? C17 C18 1.372(5) . ? C17 O2 1.390(4) . ? C19 C18 1.405(4) . ? C18 C21 1.505(5) . ? C10 C11 1.368(4) . ? C10 N2 1.394(4) . ? C23 C22 1.434(9) . ? O3 C22 1.281(9) . ? C22 C23 1.434(9) 2 ? N2 C12 1.323(4) . ? N1 C12 1.339(4) . ? N1 C11 1.382(4) . ? C11 C13 1.486(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 C6 C1 O1 121.2(3) . . ? C6 C1 C2 122.0(2) . . ? O1 C1 C2 116.7(3) . . ? C4 C5 C6 121.2(3) . . ? C2 C3 C4 122.6(3) . . ? C5 C4 C3 118.7(3) . . ? C5 C4 C9 122.3(2) . . ? C3 C4 C9 119.0(2) . . ? C1 C6 C5 118.3(3) . . ? C1 C6 C8 122.1(3) . . ? C5 C6 C8 119.6(3) . . ? C3 C2 C1 117.2(3) . . ? C3 C2 C7 121.6(3) . . ? C1 C2 C7 121.2(3) . . ? C10 C9 C14 110.9(2) . . ? C10 C9 C4 113.3(2) . . ? C14 C9 C4 113.7(2) . . ? C17 C16 C15 118.0(3) . . ? C17 C16 C20 122.8(3) . . ? C15 C16 C20 119.2(3) . . ? C19 C14 C15 117.7(3) . . ? C19 C14 C9 119.8(3) . . ? C15 C14 C9 122.4(3) . . ? C16 C15 C14 121.7(3) . . ? C18 C17 C16 122.9(3) . . ? C18 C17 O2 115.0(3) . . ? C16 C17 O2 122.1(3) . . ? C14 C19 C18 122.1(3) . . ? C17 C18 C19 117.5(3) . . ? C17 C18 C21 121.0(3) . . ? C19 C18 C21 121.5(3) . . ? C11 C10 N2 109.5(3) . . ? C11 C10 C9 128.4(3) . . ? N2 C10 C9 122.0(2) . . ? O3 C22 C23 119.1(7) . . ? O3 C22 C23 119.1(7) . 2 ? C23 C22 C23 121.9(14) . 2 ? C12 N2 C10 105.6(3) . . ? C12 N1 C11 108.4(3) . . ? N2 C12 N1 111.3(3) . . ? C10 C11 N1 105.3(3) . . ? C10 C11 C13 132.5(3) . . ? N1 C11 C13 122.2(3) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.504 _refine_diff_density_min -0.313 _refine_diff_density_rms 0.045 _database_code_depnum_ccdc_archive 'CCDC 904125' ####################################################################### # # 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_45nbp_a #TrackingRef 'DMSO.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C23 H32 N2 O4 S' _chemical_formula_weight 432.57 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' 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 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 8.2791(6) _cell_length_b 10.4599(7) _cell_length_c 26.664(2) _cell_angle_alpha 90.00 _cell_angle_beta 96.212(7) _cell_angle_gamma 90.00 _cell_volume 2295.5(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour red _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.252 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 928 _exptl_absorpt_coefficient_mu 0.172 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.20016 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details psi-scan _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8857 _diffrn_reflns_av_R_equivalents 0.0435 _diffrn_reflns_av_sigmaI/netI 0.0559 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 32 _diffrn_reflns_theta_min 3.07 _diffrn_reflns_theta_max 25.25 _reflns_number_total 4141 _reflns_number_gt 3126 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0103P)^2^+8.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4141 _refine_ls_number_parameters 291 _refine_ls_number_restraints 5 _refine_ls_R_factor_all 0.1084 _refine_ls_R_factor_gt 0.0885 _refine_ls_wR_factor_ref 0.1781 _refine_ls_wR_factor_gt 0.1671 _refine_ls_goodness_of_fit_ref 1.007 _refine_ls_restrained_S_all 1.006 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.3562(4) 0.0129(3) 0.39858(11) 0.0499(8) Uani 1 1 d . . . H1 H 0.3011 -0.0442 0.4092 0.075 Uiso 1 1 calc R . . O2 O 0.2928(4) 0.4865(4) 0.71657(14) 0.0621(10) Uani 1 1 d D . . N2 N 0.8436(4) 0.1899(4) 0.59137(15) 0.0490(9) Uani 1 1 d . . . N1 N 1.0621(4) 0.3081(4) 0.60383(16) 0.0630(12) Uani 1 1 d D . . H1M H 1.1608 0.3301 0.6133 0.076 Uiso 1 1 calc RD . . C4 C 0.5623(5) 0.2538(4) 0.51342(15) 0.0396(10) Uani 1 1 d . . . C2 C 0.5897(5) 0.1030(4) 0.44540(16) 0.0396(10) Uani 1 1 d . . . C8 C 0.1372(5) 0.1363(5) 0.4611(2) 0.0587(13) Uani 1 1 d . . . H8A H 0.0860 0.1951 0.4820 0.088 Uiso 1 1 calc R . . H8B H 0.1118 0.0503 0.4700 0.088 Uiso 1 1 calc R . . H8C H 0.0982 0.1513 0.4263 0.088 Uiso 1 1 calc R . . C15 C 0.5066(5) 0.2912(4) 0.63007(16) 0.0417(10) Uani 1 1 d . . . H15 H 0.5405 0.2075 0.6258 0.050 Uiso 1 1 calc R . . C17 C 0.3748(5) 0.4474(4) 0.67758(16) 0.0437(10) Uani 1 1 d . . . C14 C 0.5385(5) 0.3822(4) 0.59478(16) 0.0401(10) Uani 1 1 d . . . C16 C 0.4247(5) 0.3208(4) 0.67205(16) 0.0422(10) Uani 1 1 d . . . C1 C 0.4187(5) 0.0888(4) 0.43804(15) 0.0381(9) Uani 1 1 d . . . C9 C 0.6382(5) 0.3502(4) 0.55132(16) 0.0418(10) Uani 1 1 d . . . H9 H 0.6492 0.4300 0.5327 0.050 Uiso 1 1 calc R . . C3 C 0.6540(5) 0.1853(4) 0.48218(16) 0.0417(10) Uani 1 1 d . . . H3 H 0.7662 0.1960 0.4865 0.050 Uiso 1 1 calc R . . C19 C 0.4843(5) 0.5062(4) 0.60110(17) 0.0465(11) Uani 1 1 d . . . H19 H 0.5028 0.5681 0.5773 0.056 Uiso 1 1 calc R . . C12 C 0.9984(5) 0.1910(5) 0.61013(19) 0.0561(13) Uani 1 1 d . . . H12 H 1.0546 0.1218 0.6253 0.067 Uiso 1 1 calc R . . C5 C 0.3925(5) 0.2369(4) 0.50547(16) 0.0419(10) Uani 1 1 d . . . H5 H 0.3266 0.2816 0.5255 0.050 Uiso 1 1 calc R . . C18 C 0.4023(5) 0.5404(4) 0.64250(17) 0.0455(11) Uani 1 1 d . . . C6 C 0.3221(5) 0.1558(4) 0.46874(16) 0.0407(10) Uani 1 1 d . . . C7 C 0.6935(5) 0.0287(5) 0.41284(18) 0.0519(12) Uani 1 1 d . . . H7A H 0.8053 0.0524 0.4209 0.078 Uiso 1 1 calc R . . H7B H 0.6604 0.0472 0.3780 0.078 Uiso 1 1 calc R . . H7C H 0.6812 -0.0611 0.4188 0.078 Uiso 1 1 calc R . . C10 C 0.8101(5) 0.3110(4) 0.57290(17) 0.0444(11) Uani 1 1 d . . . C21 C 0.3505(7) 0.6767(5) 0.6495(2) 0.0690(16) Uani 1 1 d . . . H21A H 0.2349 0.6799 0.6502 0.103 Uiso 1 1 calc R . . H21B H 0.3804 0.7279 0.6221 0.103 Uiso 1 1 calc R . . H21C H 0.4033 0.7091 0.6808 0.103 Uiso 1 1 calc R . . C11 C 0.9451(5) 0.3864(5) 0.57992(18) 0.0525(12) Uani 1 1 d . . . C13 C 0.9735(7) 0.5228(5) 0.5690(2) 0.0786(18) Uani 1 1 d . . . H13A H 0.8865 0.5542 0.5455 0.118 Uiso 1 1 calc R . . H13B H 1.0745 0.5315 0.5547 0.118 Uiso 1 1 calc R . . H13C H 0.9781 0.5713 0.5997 0.118 Uiso 1 1 calc R . . C20 C 0.3932(6) 0.2187(5) 0.70910(19) 0.0563(13) Uani 1 1 d . . . H20A H 0.4339 0.2457 0.7425 0.084 Uiso 1 1 calc R . . H20B H 0.4471 0.1414 0.7009 0.084 Uiso 1 1 calc R . . H20C H 0.2785 0.2035 0.7076 0.084 Uiso 1 1 calc R . . S1 S 0.79313(15) 0.41621(15) 0.75350(5) 0.0644(4) Uani 1 1 d . . . O3 O 0.9092(5) 0.4529(5) 0.79792(14) 0.0881(14) Uani 1 1 d . . . C22 C 0.8375(7) 0.5118(6) 0.7025(2) 0.0750(16) Uani 1 1 d . . . H22A H 0.8047 0.5983 0.7079 0.113 Uiso 1 1 calc R . . H22B H 0.7797 0.4799 0.6719 0.113 Uiso 1 1 calc R . . H22C H 0.9521 0.5094 0.6998 0.113 Uiso 1 1 calc R . . C23 C 0.8610(7) 0.2694(5) 0.7299(2) 0.0740(16) Uani 1 1 d . . . H23A H 0.9755 0.2744 0.7271 0.111 Uiso 1 1 calc R . . H23B H 0.8039 0.2530 0.6972 0.111 Uiso 1 1 calc R . . H23C H 0.8403 0.2014 0.7525 0.111 Uiso 1 1 calc R . . O4 O 0.7690(5) 0.8747(5) 0.69619(17) 0.0760(11) Uani 1 1 d D . . H4N H 0.741(6) 0.896(5) 0.6651(9) 0.060(16) Uiso 1 1 d D . . H2 H 0.303(6) 0.436(4) 0.7423(13) 0.057(16) Uiso 1 1 d D . . H4M H 0.772(17) 0.952(4) 0.706(5) 0.29(7) Uiso 1 1 d 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 O1 0.0378(17) 0.052(2) 0.061(2) -0.0062(16) 0.0080(14) -0.0071(15) O2 0.064(2) 0.060(2) 0.067(2) 0.0007(19) 0.0291(19) 0.0129(19) N2 0.0260(18) 0.050(2) 0.070(3) -0.008(2) 0.0042(16) 0.0018(17) N1 0.025(2) 0.080(3) 0.083(3) -0.016(3) 0.0038(19) -0.006(2) C4 0.029(2) 0.043(2) 0.048(2) -0.001(2) 0.0081(17) -0.0005(19) C2 0.032(2) 0.038(2) 0.050(2) -0.0040(19) 0.0108(18) -0.0007(19) C8 0.021(2) 0.064(3) 0.092(4) -0.012(3) 0.009(2) -0.005(2) C15 0.029(2) 0.038(2) 0.058(3) -0.003(2) 0.0046(18) 0.0030(18) C17 0.031(2) 0.051(3) 0.051(3) -0.005(2) 0.0080(18) 0.001(2) C14 0.026(2) 0.044(2) 0.051(3) -0.003(2) 0.0033(17) -0.0013(18) C16 0.026(2) 0.045(3) 0.056(3) 0.001(2) 0.0030(18) -0.0029(19) C1 0.031(2) 0.037(2) 0.047(2) -0.0018(19) 0.0033(17) 0.0008(18) C9 0.027(2) 0.042(2) 0.057(3) -0.003(2) 0.0085(18) 0.0009(18) C3 0.0198(19) 0.047(3) 0.059(3) -0.003(2) 0.0099(17) 0.0015(18) C19 0.043(3) 0.043(3) 0.053(3) 0.000(2) 0.005(2) -0.004(2) C12 0.034(3) 0.062(3) 0.072(3) -0.012(3) 0.003(2) 0.011(2) C5 0.025(2) 0.045(3) 0.057(3) -0.005(2) 0.0109(18) 0.0052(19) C18 0.041(2) 0.041(3) 0.055(3) -0.003(2) 0.006(2) 0.003(2) C6 0.023(2) 0.043(2) 0.056(3) 0.001(2) 0.0043(17) -0.0012(18) C7 0.036(2) 0.050(3) 0.072(3) -0.011(2) 0.017(2) -0.002(2) C10 0.027(2) 0.050(3) 0.057(3) -0.008(2) 0.0093(18) -0.002(2) C21 0.084(4) 0.048(3) 0.078(4) 0.002(3) 0.026(3) 0.017(3) C11 0.033(2) 0.057(3) 0.067(3) -0.009(2) 0.005(2) -0.007(2) C13 0.060(4) 0.065(4) 0.110(5) -0.003(3) 0.008(3) -0.028(3) C20 0.045(3) 0.053(3) 0.073(3) 0.009(2) 0.018(2) 0.005(2) S1 0.0387(7) 0.0816(10) 0.0745(9) -0.0108(7) 0.0127(6) 0.0026(7) O3 0.064(2) 0.131(4) 0.069(2) -0.027(3) 0.0061(19) 0.011(3) C22 0.061(4) 0.080(4) 0.082(4) -0.008(3) 0.002(3) 0.000(3) C23 0.056(3) 0.066(4) 0.101(4) -0.005(3) 0.013(3) 0.001(3) O4 0.066(3) 0.098(3) 0.066(3) 0.010(2) 0.011(2) -0.005(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.374(5) . ? O2 C17 1.364(5) . ? N2 C12 1.324(5) . ? N2 C10 1.376(6) . ? N1 C12 1.351(6) . ? N1 C11 1.372(6) . ? C4 C3 1.385(5) . ? C4 C5 1.410(5) . ? C4 C9 1.515(6) . ? C2 C3 1.368(6) . ? C2 C1 1.416(5) . ? C2 C7 1.503(5) . ? C8 C6 1.536(5) . ? C15 C14 1.383(6) . ? C15 C16 1.404(6) . ? C17 C18 1.385(6) . ? C17 C16 1.400(6) . ? C14 C19 1.389(6) . ? C14 C9 1.531(5) . ? C16 C20 1.497(6) . ? C1 C6 1.394(6) . ? C9 C10 1.532(6) . ? C19 C18 1.404(6) . ? C5 C6 1.377(6) . ? C18 C21 1.506(6) . ? C10 C11 1.364(6) . ? C11 C13 1.480(7) . ? S1 O3 1.493(4) . ? S1 C22 1.758(6) . ? S1 C23 1.774(6) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C12 N2 C10 106.1(4) . . ? C12 N1 C11 109.5(4) . . ? C3 C4 C5 116.6(4) . . ? C3 C4 C9 122.0(4) . . ? C5 C4 C9 121.2(4) . . ? C3 C2 C1 118.1(4) . . ? C3 C2 C7 122.5(4) . . ? C1 C2 C7 119.4(4) . . ? C14 C15 C16 122.3(4) . . ? O2 C17 C18 115.8(4) . . ? O2 C17 C16 122.7(4) . . ? C18 C17 C16 121.4(4) . . ? C15 C14 C19 118.2(4) . . ? C15 C14 C9 121.5(4) . . ? C19 C14 C9 120.2(4) . . ? C17 C16 C15 117.8(4) . . ? C17 C16 C20 122.1(4) . . ? C15 C16 C20 120.2(4) . . ? O1 C1 C6 123.2(4) . . ? O1 C1 C2 117.0(3) . . ? C6 C1 C2 119.6(4) . . ? C4 C9 C14 115.6(3) . . ? C4 C9 C10 112.0(3) . . ? C14 C9 C10 109.2(3) . . ? C2 C3 C4 124.1(4) . . ? C14 C19 C18 121.6(4) . . ? N2 C12 N1 109.6(5) . . ? C6 C5 C4 121.5(4) . . ? C17 C18 C19 118.8(4) . . ? C17 C18 C21 120.7(4) . . ? C19 C18 C21 120.5(4) . . ? C5 C6 C1 120.1(4) . . ? C5 C6 C8 121.1(4) . . ? C1 C6 C8 118.8(4) . . ? C11 C10 N2 110.6(4) . . ? C11 C10 C9 127.7(4) . . ? N2 C10 C9 121.6(4) . . ? C10 C11 N1 104.2(4) . . ? C10 C11 C13 132.5(5) . . ? N1 C11 C13 123.2(4) . . ? O3 S1 C22 107.3(3) . . ? O3 S1 C23 107.6(3) . . ? C22 S1 C23 96.7(3) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.25 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.447 _refine_diff_density_min -0.406 _refine_diff_density_rms 0.069 _database_code_depnum_ccdc_archive 'CCDC 904123'