# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # 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_new _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C H N O S' _chemical_formula_weight 75.09 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 Orthorhombic _symmetry_space_group_name_H-M Pbca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 13.4815(4) _cell_length_b 8.2127(3) _cell_length_c 28.9529(9) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3205.65(18) _cell_formula_units_Z 42 _cell_measurement_temperature 273(2) _cell_measurement_reflns_used 4864 _cell_measurement_theta_min 0.00 _cell_measurement_theta_max 0.00 _exptl_crystal_description Block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.634 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1596 _exptl_absorpt_coefficient_mu 0.781 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7716 _exptl_absorpt_correction_T_max 0.8594 _exptl_absorpt_process_details 'SADABS (BRuker,2004)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 273(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEXII 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 10575 _diffrn_reflns_av_R_equivalents 0.0222 _diffrn_reflns_av_sigmaI/netI 0.0174 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -34 _diffrn_reflns_limit_l_max 33 _diffrn_reflns_theta_min 1.41 _diffrn_reflns_theta_max 24.99 _reflns_number_total 2401 _reflns_number_gt 1987 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEXII, Bruker,2004' _computing_cell_refinement 'APEXII/SAINT, Bruker,2004' _computing_data_reduction 'SAINT PLUS/XPREP, Bruker,2004' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0439P)^2^+0.6557P] 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 2401 _refine_ls_number_parameters 237 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0456 _refine_ls_R_factor_gt 0.0357 _refine_ls_wR_factor_ref 0.0894 _refine_ls_wR_factor_gt 0.0818 _refine_ls_goodness_of_fit_ref 1.089 _refine_ls_restrained_S_all 1.089 _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 0.68897(13) 0.5791(2) 0.12337(6) 0.0541(5) Uani 1 1 d . . . H1 H 0.7266 0.6410 0.1438 0.065 Uiso 1 1 calc R . . C2 C 0.68236(14) 0.6259(3) 0.07859(7) 0.0588(5) Uani 1 1 d . . . H2 H 0.7156 0.7184 0.0684 0.071 Uiso 1 1 calc R . . C3 C 0.62534(13) 0.5345(2) 0.04770(6) 0.0510(5) Uani 1 1 d . . . H3 H 0.6227 0.5645 0.0167 0.061 Uiso 1 1 calc R . . C4 C 0.57366(11) 0.4018(2) 0.06252(5) 0.0428(4) Uani 1 1 d . . . H4 H 0.5346 0.3445 0.0416 0.051 Uiso 1 1 calc R . . C5 C 0.57802(10) 0.3492(2) 0.10909(5) 0.0374(4) Uani 1 1 d . . . C6 C 0.52997(11) 0.2064(2) 0.12632(5) 0.0379(4) Uani 1 1 d . . . C7 C 0.46187(11) 0.1062(2) 0.09799(5) 0.0394(4) Uani 1 1 d . . . C8 C 0.38422(12) 0.1747(3) 0.06843(5) 0.0429(5) Uani 1 1 d . . . C9 C 0.32761(14) 0.0599(3) 0.03790(6) 0.0590(5) Uani 1 1 d . . . H9A H 0.3166 0.1120 0.0083 0.071 Uiso 1 1 calc R . . H9B H 0.2632 0.0396 0.0517 0.071 Uiso 1 1 calc R . . C10 C 0.37854(15) -0.1010(3) 0.02990(6) 0.0630(6) Uani 1 1 d . . . H10A H 0.4372 -0.0846 0.0111 0.076 Uiso 1 1 calc R . . H10B H 0.3343 -0.1739 0.0134 0.076 Uiso 1 1 calc R . . C11 C 0.40775(14) -0.1767(3) 0.07560(7) 0.0594(6) Uani 1 1 d . . . H11A H 0.3488 -0.2143 0.0916 0.071 Uiso 1 1 calc R . . H11B H 0.4502 -0.2701 0.0701 0.071 Uiso 1 1 calc R . . C12 C 0.46101(12) -0.0562(3) 0.10492(6) 0.0467(5) Uani 1 1 d . . . C13 C 0.51608(14) -0.0208(2) 0.18096(6) 0.0535(5) Uani 1 1 d . . . H13A H 0.5597 -0.0708 0.2035 0.064 Uiso 1 1 calc R . . H13B H 0.4508 -0.0115 0.1948 0.064 Uiso 1 1 calc R . . C14 C 0.55397(11) 0.1460(2) 0.16960(5) 0.0396(4) Uani 1 1 d . . . C15 C 0.61543(11) 0.2362(2) 0.20048(5) 0.0403(4) Uani 1 1 d . A . C16 C 0.65382(12) 0.3812(2) 0.18532(6) 0.0451(5) Uani 1 1 d . . . H16 H 0.6904 0.4443 0.2058 0.054 Uiso 1 1 calc R . . C17 C 0.64005(11) 0.4388(2) 0.13976(5) 0.0413(4) Uani 1 1 d . . . C18 C 0.63898(14) 0.1778(2) 0.24747(6) 0.0463(5) Uani 1 1 d . . . S1 S 0.7529(2) 0.2172(3) 0.27076(7) 0.0603(5) Uani 0.658(4) 1 d P A 1 C19 C 0.5818(10) 0.0988(19) 0.2779(5) 0.068(4) Uani 0.658(4) 1 d P A 1 H19 H 0.5170 0.0667 0.2718 0.081 Uiso 0.658(4) 1 calc PR A 1 S1A S 0.5603(7) 0.0721(12) 0.2826(3) 0.0613(12) Uani 0.326(4) 1 d P A 2 C19A C 0.7272(14) 0.224(3) 0.2696(6) 0.094(10) Uani 0.326(4) 1 d P A 2 H19A H 0.7767 0.2919 0.2583 0.113 Uiso 0.326(4) 1 calc PR A 2 C20 C 0.63343(19) 0.0675(3) 0.32306(7) 0.0748(7) Uani 1 1 d . . . H20 H 0.6071 0.0137 0.3485 0.090 Uiso 1 1 calc R A 1 C21 C 0.72395(18) 0.1313(3) 0.31978(7) 0.0753(7) Uani 1 1 d . A . H21 H 0.7686 0.1271 0.3442 0.090 Uiso 1 1 calc R B 1 O1 O 0.51013(9) -0.12402(16) 0.14059(4) 0.0587(4) Uani 1 1 d . . . O2 O 0.36099(9) 0.31890(19) 0.07004(4) 0.0559(4) 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 0.0512(10) 0.0441(14) 0.0669(11) -0.0051(9) -0.0063(8) -0.0123(10) C2 0.0548(11) 0.0500(14) 0.0716(12) 0.0095(10) 0.0016(9) -0.0150(10) C3 0.0473(10) 0.0517(14) 0.0542(10) 0.0045(9) 0.0046(8) -0.0023(10) C4 0.0365(8) 0.0425(13) 0.0492(9) -0.0068(8) 0.0016(7) 0.0001(9) C5 0.0312(7) 0.0334(12) 0.0476(8) -0.0071(7) 0.0031(6) 0.0031(8) C6 0.0305(7) 0.0334(12) 0.0498(9) -0.0075(8) 0.0009(6) 0.0022(8) C7 0.0352(8) 0.0346(13) 0.0486(9) -0.0068(8) 0.0030(6) -0.0020(8) C8 0.0355(8) 0.0499(15) 0.0433(9) -0.0029(8) 0.0039(6) -0.0059(9) C9 0.0594(11) 0.0635(15) 0.0540(10) -0.0022(10) -0.0104(8) -0.0177(11) C10 0.0649(12) 0.0682(17) 0.0558(11) -0.0204(10) 0.0100(9) -0.0275(12) C11 0.0550(11) 0.0446(14) 0.0786(13) -0.0171(10) 0.0019(9) -0.0090(10) C12 0.0374(9) 0.0415(15) 0.0612(10) -0.0089(9) 0.0003(7) -0.0007(9) C13 0.0547(10) 0.0438(14) 0.0620(11) 0.0023(9) -0.0109(8) -0.0065(10) C14 0.0334(8) 0.0328(12) 0.0527(9) -0.0031(8) 0.0012(7) 0.0000(8) C15 0.0346(8) 0.0391(12) 0.0474(9) -0.0062(8) 0.0017(6) 0.0017(8) C16 0.0407(8) 0.0439(13) 0.0509(9) -0.0126(8) -0.0038(7) -0.0032(9) C17 0.0346(8) 0.0350(12) 0.0542(9) -0.0064(8) 0.0012(7) -0.0004(8) C18 0.0449(10) 0.0462(13) 0.0479(9) -0.0071(9) -0.0002(9) 0.0027(9) S1 0.0546(9) 0.0760(10) 0.0503(6) -0.0163(6) -0.0133(5) 0.0044(6) C19 0.067(7) 0.075(8) 0.061(5) 0.002(4) 0.004(4) 0.010(5) S1A 0.069(3) 0.061(2) 0.0539(14) 0.0049(13) 0.0135(14) -0.0092(16) C19A 0.099(18) 0.118(14) 0.065(9) 0.032(8) 0.026(9) 0.013(9) C20 0.0979(18) 0.0696(18) 0.0571(12) 0.0016(11) 0.0113(11) 0.0067(14) C21 0.0851(16) 0.089(2) 0.0515(11) -0.0133(11) -0.0150(10) 0.0174(15) O1 0.0606(8) 0.0349(9) 0.0807(9) -0.0045(7) -0.0142(7) -0.0003(6) O2 0.0464(7) 0.0558(11) 0.0654(8) -0.0033(7) -0.0087(5) 0.0073(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.355(3) . ? C1 C17 1.410(3) . ? C2 C3 1.398(3) . ? C3 C4 1.363(3) . ? C4 C5 1.417(2) . ? C5 C17 1.424(2) . ? C5 C6 1.429(2) . ? C6 C14 1.386(2) . ? C6 C7 1.481(2) . ? C7 C12 1.349(3) . ? C7 C8 1.464(2) . ? C8 O2 1.226(2) . ? C8 C9 1.501(3) . ? C9 C10 1.507(3) . ? C10 C11 1.514(3) . ? C11 C12 1.489(3) . ? C12 O1 1.347(2) . ? C13 O1 1.446(2) . ? C13 C14 1.498(3) . ? C14 C15 1.427(2) . ? C15 C16 1.371(2) . ? C15 C18 1.477(2) . ? C16 C17 1.413(2) . ? C18 C19 1.339(10) . ? C18 C19A 1.403(18) . ? C18 S1A 1.707(8) . ? C18 S1 1.708(2) . ? S1 C21 1.632(4) . ? C19 C20 1.502(16) . ? S1A C20 1.533(10) . ? C19A C21 1.64(2) . ? C20 C21 1.331(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 C2 C1 C17 121.52(17) . . ? C1 C2 C3 119.73(18) . . ? C4 C3 C2 120.60(17) . . ? C3 C4 C5 121.49(16) . . ? C4 C5 C17 117.38(15) . . ? C4 C5 C6 124.30(15) . . ? C17 C5 C6 118.17(15) . . ? C14 C6 C5 120.23(14) . . ? C14 C6 C7 116.51(15) . . ? C5 C6 C7 122.92(14) . . ? C12 C7 C8 117.42(16) . . ? C12 C7 C6 118.19(15) . . ? C8 C7 C6 123.60(17) . . ? O2 C8 C7 122.09(16) . . ? O2 C8 C9 119.97(16) . . ? C7 C8 C9 117.80(18) . . ? C8 C9 C10 114.18(16) . . ? C9 C10 C11 110.14(15) . . ? C12 C11 C10 110.53(17) . . ? O1 C12 C7 121.25(16) . . ? O1 C12 C11 113.52(18) . . ? C7 C12 C11 125.23(17) . . ? O1 C13 C14 112.17(14) . . ? C6 C14 C15 121.08(16) . . ? C6 C14 C13 116.51(14) . . ? C15 C14 C13 122.35(15) . . ? C16 C15 C14 118.03(15) . . ? C16 C15 C18 119.72(15) . . ? C14 C15 C18 122.25(17) . . ? C15 C16 C17 122.66(15) . . ? C1 C17 C16 121.72(15) . . ? C1 C17 C5 119.15(15) . . ? C16 C17 C5 119.09(16) . . ? C19 C18 C19A 108.5(11) . . ? C19 C18 C15 129.8(7) . . ? C19A C18 C15 121.0(9) . . ? C19 C18 S1A 4.7(10) . . ? C19A C18 S1A 113.1(9) . . ? C15 C18 S1A 125.4(3) . . ? C19 C18 S1 110.4(7) . . ? C19A C18 S1 6.5(9) . . ? C15 C18 S1 119.71(17) . . ? S1A C18 S1 114.8(3) . . ? C21 S1 C18 92.69(18) . . ? C18 C19 C20 112.9(10) . . ? C20 S1A C18 93.9(5) . . ? C18 C19A C21 104.9(13) . . ? C21 C20 C19 107.2(4) . . ? C21 C20 S1A 121.7(3) . . ? C19 C20 S1A 14.7(6) . . ? C20 C21 S1 116.80(19) . . ? C20 C21 C19A 105.7(7) . . ? S1 C21 C19A 12.3(7) . . ? C12 O1 C13 113.84(14) . . ? _diffrn_measured_fraction_theta_max 0.853 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.853 _refine_diff_density_max 0.135 _refine_diff_density_min -0.199 _refine_diff_density_rms 0.043 _database_code_depnum_ccdc_archive 'CCDC 948676'