# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2010 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'T Chandrashekar' _publ_contact_author_email TKC@IITK.AC.IN _publ_section_title ; Fused Core-Modified meso-Aryl Expanded Porphyrins ; loop_ _publ_author_name 'T Chandrashekar' 'S Gokulnath' 'Viswanathan PrabhuRaja' 'R Sabarinathan' ; A.Srinivasan ; # Attachment '694219-Revised.cif' data_sn52 _database_code_depnum_ccdc_archive 'CCDC 694219' #TrackingRef '694219-Revised.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common monofusedrubyrin _chemical_formula_moiety ? _chemical_formula_sum 'C64 H52 N2 S5' _chemical_formula_weight 1009.38 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1)/n 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 14.623(3) _cell_length_b 15.092(3) _cell_length_c 15.929(3) _cell_angle_alpha 90.00 _cell_angle_beta 114.98(3) _cell_angle_gamma 90.00 _cell_volume 3186.6(11) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 6342 _cell_measurement_theta_min 2.76 _cell_measurement_theta_max 24.84 _exptl_crystal_description parallelopiped _exptl_crystal_colour green _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.052 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1060 _exptl_absorpt_coefficient_mu 0.218 _exptl_absorpt_correction_type empirical _exptl_absorpt_process_details 'BRUKER SADABS' _exptl_absorpt_correction_T_min 0.9578 _exptl_absorpt_correction_T_max 0.9786 _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'BRUKER SMART APEX CCD DIFFRACTOMETER' _diffrn_measurement_method 'omega-phi scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 45977 _diffrn_reflns_av_R_equivalents 0.0430 _diffrn_reflns_av_sigmaI/netI 0.0267 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.49 _diffrn_reflns_theta_max 25.50 _reflns_number_total 5924 _reflns_number_gt 5147 _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 ORTEP _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. The difmap phased on the non-hydrogen atoms of the complex molecule showed two regions centered at (0,0,0.5) and (0.5,0,1), respectively, containing peaks due to severely disordered solvent. No consistent models for dichloromethane or hexane molecules could be assembled from these peaks. This part of the structure was modeled by using the SQUEEZE procedure of PLATON (Spek, 1995), which indicated the presence of two cavities of 395 cubic Angstroms each occupied by 85.3 electrons.a new set of F2 (hkl) values with the contribution from solvent molecules withdrawn was obtained by the SQUEEZE and refined further. It is observed that sulphur atom S3 posseses half-occupancy between two sites related by a crystallographic centre of inversion for this compound. i.e. two independent molecules are overlapped with opposite orientation. Hence in the isotropic refinement the ring carbons involving S3 ( C1,C14, C2and C3) has shown higher temperature factors in the isotropic refinement. Modelling of this positional disorder and location and fixing the hydrogen atom on this ring was difficult.Hence the carbons atoms ( C1,C14, C2and C3) of the five mebembered ring involving S3 is refined only isotropically and the distances between the atoms in this five mebered ring is restrained by using DFIX and DANG commands. ; _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^)+(0.0699P)^2^+8.6813P] 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 5924 _refine_ls_number_parameters 311 _refine_ls_number_restraints 10 _refine_ls_R_factor_all 0.0948 _refine_ls_R_factor_gt 0.0843 _refine_ls_wR_factor_ref 0.2006 _refine_ls_wR_factor_gt 0.1933 _refine_ls_goodness_of_fit_ref 1.047 _refine_ls_restrained_S_all 1.050 _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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C2 C -0.0042(4) 0.4495(3) 0.1866(3) 0.0607(12) Uiso 1 d D . . C3 C -0.0295(4) 0.4183(3) 0.2544(3) 0.0607(12) Uiso 1 d D . . C4 C -0.1228(3) 0.3779(3) 0.2219(3) 0.0433(9) Uani 1 d . . . H4 H -0.1498 0.3531 0.2599 0.052 Uiso 1 calc R . . C5 C -0.1720(3) 0.3785(2) 0.1252(2) 0.0336(8) Uani 1 d . . . S2 S -0.09791(7) 0.43029(7) 0.07768(9) 0.0475(3) Uani 1 d . . . C1 C 0.1502(3) 0.5011(3) 0.3077(3) 0.0559(11) Uiso 1 d D . . S3 S 0.07743(13) 0.44791(13) 0.34906(11) 0.0342(4) Uani 0.50 d PD . . S1 S 0.14515(7) 0.53872(7) 0.14776(8) 0.0488(3) Uani 1 d . . . N1 N 0.2771(2) 0.62398(19) 0.08059(18) 0.0286(6) Uani 1 d . . . C12 C 0.2506(2) 0.5705(2) 0.2477(2) 0.0287(7) Uani 1 d . . . C21 C 0.4192(2) 0.6352(2) 0.3411(2) 0.0259(7) Uani 1 d . . . C22 C 0.4976(2) 0.5743(2) 0.3823(2) 0.0294(7) Uani 1 d . . . C26 C 0.4172(2) 0.7140(2) 0.3868(2) 0.0298(7) Uani 1 d . . . C10 C 0.3469(2) 0.6396(2) 0.1684(2) 0.0280(7) Uani 1 d . . . C23 C 0.5733(2) 0.5941(2) 0.4693(2) 0.0321(8) Uani 1 d . . . H23 H 0.6256 0.5538 0.4970 0.038 Uiso 1 calc R . . C11 C 0.3354(2) 0.6145(2) 0.2479(2) 0.0274(7) Uani 1 d . . . C15 C 0.3233(3) 0.6962(2) -0.1246(2) 0.0310(7) Uani 1 d . . . C31 C 0.6575(3) 0.6907(3) 0.6098(2) 0.0404(9) Uani 1 d . . . H31A H 0.6570 0.6472 0.6535 0.061 Uiso 1 calc R . . H31B H 0.6478 0.7485 0.6298 0.061 Uiso 1 calc R . . H31C H 0.7211 0.6888 0.6057 0.061 Uiso 1 calc R . . C25 C 0.4947(3) 0.7304(2) 0.4741(2) 0.0311(7) Uani 1 d . . . H25 H 0.4933 0.7823 0.5049 0.037 Uiso 1 calc R . . C7 C 0.3163(2) 0.6589(2) 0.0249(2) 0.0308(7) Uani 1 d . . . C6 C 0.2682(2) 0.6576(2) -0.0726(2) 0.0295(7) Uani 1 d . . . C24 C 0.5736(2) 0.6713(2) 0.5160(2) 0.0305(7) Uani 1 d . . . C32 C 0.5031(3) 0.4898(3) 0.3351(3) 0.0381(8) Uani 1 d . . . H32A H 0.5293 0.5019 0.2903 0.057 Uiso 1 calc R . . H32B H 0.4368 0.4646 0.3045 0.057 Uiso 1 calc R . . H32C H 0.5467 0.4486 0.3802 0.057 Uiso 1 calc R . . C16 C 0.3843(3) 0.6413(3) -0.1502(3) 0.0397(9) Uani 1 d . . . C13 C 0.2393(3) 0.5446(2) 0.3274(3) 0.0369(8) Uani 1 d . . . H13 H 0.2872 0.5557 0.3873 0.044 Uiso 1 calc R . . C9 C 0.4340(3) 0.6855(3) 0.1682(2) 0.0358(8) Uani 1 d . . . H9 H 0.4914 0.7030 0.2196 0.043 Uiso 1 calc R . . C8 C 0.4155(3) 0.6977(3) 0.0788(2) 0.0369(8) Uani 1 d . . . H8 H 0.4573 0.7252 0.0560 0.044 Uiso 1 calc R . . C20 C 0.3149(3) 0.7864(3) -0.1470(3) 0.0381(8) Uani 1 d . . . C30 C 0.3341(3) 0.7808(3) 0.3422(3) 0.0412(9) Uani 1 d . . . H30A H 0.3373 0.8039 0.2873 0.062 Uiso 1 calc R . . H30B H 0.3422 0.8283 0.3848 0.062 Uiso 1 calc R . . H30C H 0.2700 0.7528 0.3260 0.062 Uiso 1 calc R . . C19 C 0.3684(3) 0.8202(3) -0.1943(3) 0.0467(10) Uani 1 d . . . H19 H 0.3626 0.8801 -0.2093 0.056 Uiso 1 calc R . . C14 C 0.0901(4) 0.4921(3) 0.2133(3) 0.0598(12) Uiso 1 d D . . C17 C 0.4366(3) 0.6786(3) -0.1969(3) 0.0490(10) Uani 1 d . . . H17 H 0.4776 0.6423 -0.2135 0.059 Uiso 1 calc R . . C18 C 0.4298(3) 0.7676(3) -0.2195(3) 0.0470(10) Uani 1 d . . . C27 C 0.3923(4) 0.5436(3) -0.1287(4) 0.0626(13) Uani 1 d . . . H27A H 0.3289 0.5155 -0.1650 0.094 Uiso 1 calc R . . H27B H 0.4092 0.5352 -0.0641 0.094 Uiso 1 calc R . . H27C H 0.4439 0.5179 -0.1433 0.094 Uiso 1 calc R . . C29 C 0.2492(4) 0.8462(3) -0.1200(4) 0.0611(13) Uani 1 d . . . H29A H 0.1838 0.8198 -0.1389 0.092 Uiso 1 calc R . . H29B H 0.2425 0.9026 -0.1500 0.092 Uiso 1 calc R . . H29C H 0.2795 0.8543 -0.0541 0.092 Uiso 1 calc R . . C28 C 0.4889(4) 0.8046(4) -0.2699(4) 0.0690(15) Uani 1 d . . . H28A H 0.4550 0.8558 -0.3049 0.103 Uiso 1 calc R . . H28B H 0.4940 0.7604 -0.3111 0.103 Uiso 1 calc R . . H28C H 0.5553 0.8209 -0.2257 0.103 Uiso 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 C4 0.040(2) 0.051(2) 0.0278(18) -0.0090(17) 0.0028(16) -0.0049(18) C5 0.0318(18) 0.0401(19) 0.0305(18) -0.0065(15) 0.0146(15) -0.0054(15) S2 0.0367(5) 0.0382(5) 0.0802(8) -0.0104(5) 0.0371(5) -0.0104(4) S3 0.0336(9) 0.0511(11) 0.0142(7) 0.0029(7) 0.0066(6) -0.0100(8) S1 0.0235(4) 0.0424(6) 0.0597(7) -0.0227(5) -0.0028(4) -0.0022(4) N1 0.0269(14) 0.0383(16) 0.0196(13) -0.0035(11) 0.0088(11) -0.0058(12) C12 0.0258(16) 0.0322(17) 0.0234(15) -0.0026(13) 0.0059(13) -0.0015(13) C21 0.0233(15) 0.0349(17) 0.0169(14) 0.0021(13) 0.0059(13) -0.0067(13) C22 0.0265(16) 0.0359(18) 0.0262(16) -0.0003(14) 0.0115(14) -0.0058(14) C26 0.0295(17) 0.0347(18) 0.0221(16) 0.0003(13) 0.0078(14) -0.0039(14) C10 0.0243(16) 0.0349(18) 0.0203(15) -0.0038(13) 0.0049(13) -0.0051(13) C23 0.0230(16) 0.042(2) 0.0267(17) 0.0052(15) 0.0061(13) 0.0004(14) C11 0.0240(16) 0.0307(17) 0.0228(16) -0.0025(13) 0.0052(13) -0.0030(13) C15 0.0305(17) 0.041(2) 0.0214(16) -0.0049(14) 0.0111(14) -0.0093(15) C31 0.0334(19) 0.053(2) 0.0247(17) 0.0017(16) 0.0025(15) -0.0085(17) C25 0.0331(18) 0.0355(18) 0.0206(16) -0.0044(13) 0.0072(14) -0.0070(15) C7 0.0287(17) 0.0387(19) 0.0272(17) -0.0040(14) 0.0138(14) -0.0087(14) C6 0.0265(16) 0.0380(18) 0.0257(16) -0.0045(14) 0.0126(14) -0.0050(14) C24 0.0253(16) 0.0415(19) 0.0193(15) 0.0010(14) 0.0042(13) -0.0091(14) C32 0.0343(19) 0.043(2) 0.0339(19) -0.0037(16) 0.0109(16) 0.0020(16) C16 0.046(2) 0.042(2) 0.041(2) -0.0059(16) 0.0275(18) -0.0070(17) C13 0.0345(19) 0.041(2) 0.0365(19) 0.0104(16) 0.0160(16) 0.0024(16) C9 0.0286(17) 0.047(2) 0.0235(17) -0.0027(15) 0.0030(14) -0.0120(15) C8 0.0310(18) 0.050(2) 0.0292(18) -0.0052(16) 0.0122(15) -0.0153(16) C20 0.043(2) 0.041(2) 0.0343(19) -0.0012(16) 0.0206(17) -0.0044(17) C30 0.041(2) 0.038(2) 0.0307(19) -0.0018(15) 0.0018(16) 0.0008(16) C19 0.066(3) 0.038(2) 0.047(2) -0.0047(18) 0.034(2) -0.0136(19) C17 0.059(3) 0.049(2) 0.056(3) -0.010(2) 0.041(2) -0.006(2) C18 0.061(3) 0.048(2) 0.046(2) -0.0121(19) 0.036(2) -0.021(2) C27 0.080(3) 0.047(3) 0.088(4) 0.003(2) 0.061(3) 0.006(2) C29 0.079(3) 0.051(3) 0.073(3) 0.005(2) 0.051(3) 0.011(2) C28 0.095(4) 0.068(3) 0.074(3) -0.011(3) 0.065(3) -0.028(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C2 C3 1.365(6) . ? C2 C14 1.415(6) . ? C2 S2 1.721(5) . ? C3 C4 1.380(6) . ? C3 S3 1.710(5) . ? C4 C5 1.398(5) . ? C5 C6 1.409(5) 3_565 ? C5 S2 1.746(4) . ? C1 C13 1.372(6) . ? C1 C14 1.390(6) . ? C1 S3 1.674(5) . ? S1 C14 1.715(5) . ? S1 C12 1.752(3) . ? N1 C7 1.351(4) . ? N1 C10 1.360(4) . ? C12 C13 1.403(5) . ? C12 C11 1.405(5) . ? C21 C22 1.397(5) . ? C21 C26 1.400(5) . ? C21 C11 1.506(4) . ? C22 C23 1.392(5) . ? C22 C32 1.502(5) . ? C26 C25 1.395(4) . ? C26 C30 1.506(5) . ? C10 C11 1.399(5) . ? C10 C9 1.452(5) . ? C23 C24 1.382(5) . ? C15 C20 1.399(5) . ? C15 C16 1.399(5) . ? C15 C6 1.496(4) . ? C31 C24 1.508(4) . ? C25 C24 1.386(5) . ? C7 C6 1.408(5) . ? C7 C8 1.460(5) . ? C6 C5 1.409(5) 3_565 ? C16 C17 1.390(5) . ? C16 C27 1.507(6) . ? C9 C8 1.344(5) . ? C20 C19 1.392(5) . ? C20 C29 1.507(6) . ? C19 C18 1.380(6) . ? C17 C18 1.383(6) . ? C18 C28 1.514(5) . ? 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 C2 C14 118.3(5) . . ? C3 C2 S2 111.9(4) . . ? C14 C2 S2 129.8(4) . . ? C2 C3 C4 114.2(4) . . ? C2 C3 S3 98.9(4) . . ? C4 C3 S3 146.8(4) . . ? C3 C4 C5 112.2(4) . . ? C4 C5 C6 125.0(3) . 3_565 ? C4 C5 S2 110.8(3) . . ? C6 C5 S2 124.2(3) 3_565 . ? C2 S2 C5 90.8(2) . . ? C13 C1 C14 113.5(4) . . ? C13 C1 S3 147.1(4) . . ? C14 C1 S3 99.4(3) . . ? C1 S3 C3 105.9(2) . . ? C14 S1 C12 91.0(2) . . ? C7 N1 C10 105.4(3) . . ? C13 C12 C11 124.8(3) . . ? C13 C12 S1 110.5(3) . . ? C11 C12 S1 124.7(3) . . ? C22 C21 C26 120.5(3) . . ? C22 C21 C11 119.5(3) . . ? C26 C21 C11 120.1(3) . . ? C23 C22 C21 118.5(3) . . ? C23 C22 C32 119.5(3) . . ? C21 C22 C32 122.0(3) . . ? C25 C26 C21 118.8(3) . . ? C25 C26 C30 120.3(3) . . ? C21 C26 C30 120.9(3) . . ? N1 C10 C11 124.0(3) . . ? N1 C10 C9 111.0(3) . . ? C11 C10 C9 125.0(3) . . ? C24 C23 C22 122.4(3) . . ? C10 C11 C12 124.7(3) . . ? C10 C11 C21 118.5(3) . . ? C12 C11 C21 116.8(3) . . ? C20 C15 C16 120.0(3) . . ? C20 C15 C6 120.6(3) . . ? C16 C15 C6 119.3(3) . . ? C24 C25 C26 121.8(3) . . ? N1 C7 C6 124.5(3) . . ? N1 C7 C8 111.2(3) . . ? C6 C7 C8 124.3(3) . . ? C7 C6 C5 124.7(3) . 3_565 ? C7 C6 C15 118.1(3) . . ? C5 C6 C15 117.2(3) 3_565 . ? C23 C24 C25 118.1(3) . . ? C23 C24 C31 120.9(3) . . ? C25 C24 C31 121.1(3) . . ? C17 C16 C15 118.5(4) . . ? C17 C16 C27 120.7(4) . . ? C15 C16 C27 120.8(3) . . ? C1 C13 C12 113.0(4) . . ? C8 C9 C10 106.5(3) . . ? C9 C8 C7 105.9(3) . . ? C19 C20 C15 119.1(4) . . ? C19 C20 C29 120.4(4) . . ? C15 C20 C29 120.5(3) . . ? C18 C19 C20 122.0(4) . . ? C1 C14 C2 117.4(4) . . ? C1 C14 S1 112.0(4) . . ? C2 C14 S1 130.6(4) . . ? C18 C17 C16 122.5(4) . . ? C19 C18 C17 117.8(4) . . ? C19 C18 C28 122.0(4) . . ? C17 C18 C28 120.2(4) . . ? _diffrn_measured_fraction_theta_max 0.958 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.958 _refine_diff_density_max 1.562 _refine_diff_density_min -0.866 _refine_diff_density_rms 0.074 loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons 1 0.000 0.500 0.500 394.5 146.7 2 0.500 0.000 1.000 394.3 146.7 _platon_squeeze_details ; ; # Attachment '694220-corrected.cif' data_s6n2 _database_code_depnum_ccdc_archive 'CCDC 694220' #TrackingRef '694220-corrected.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common doublyfusedrubyrin _chemical_melting_point ? _chemical_formula_moiety 'C64 H52 N2 S6' _chemical_formula_sum 'C64 H52 N2 S6' _chemical_formula_weight 1041.5 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' 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 'P 2(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 14.784(3) _cell_length_b 15.083(3) _cell_length_c 16.781(7) _cell_angle_alpha 90.00 _cell_angle_beta 117.69(2) _cell_angle_gamma 90.00 _cell_volume 3313.4(17) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description parallelopiped _exptl_crystal_colour green _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 0.857 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 856 _exptl_absorpt_coefficient_mu 0.052 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9533 _exptl_absorpt_correction_T_max 0.9763 _exptl_absorpt_process_details SADABS _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 35033 _diffrn_reflns_av_R_equivalents 0.4827 _diffrn_reflns_av_sigmaI/netI 0.1697 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.44 _diffrn_reflns_theta_max 21.96 _reflns_number_total 3902 _reflns_number_gt 1858 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'BRUKER SMART' _computing_cell_refinement 'BRUKER SMART' _computing_data_reduction 'BRUKER SMART' _computing_structure_solution 'BRUKER SHELXTL' _computing_structure_refinement 'BRUKER SHELXTL' _computing_molecular_graphics 'BRUKER SHELXTL' _computing_publication_material 'BRUKER SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.The difmap phased on the non-hydrogen atoms of the complex molecule showed two regions centered at (0.5,1,0.5) and (0.5,0.5,0) respectively, containing peaks due to severely disordered solvent. No consistent models for dichloromethane or hexane molecules could be assembled from these peaks. This part of the structure was modeled by using the SQUEEZE procedure of PLATON (Spek, 1995). A new set of F2 (hkl) values with the contribution from solvent molecules withdrawn was obtained by the SQUEEZE and refined further ; _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^)+(0.2000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3902 _refine_ls_number_parameters 331 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.3387 _refine_ls_R_factor_gt 0.2268 _refine_ls_wR_factor_ref 0.5968 _refine_ls_wR_factor_gt 0.5036 _refine_ls_goodness_of_fit_ref 1.755 _refine_ls_restrained_S_all 1.755 _refine_ls_shift/su_max 0.006 _refine_ls_shift/su_mean 0.001 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 S1 S 1.0094(4) 0.4598(3) 0.3636(3) 0.0594(17) Uani 1 1 d . . . S2 S 1.1720(4) 0.4319(3) 0.5653(3) 0.0606(17) Uani 1 1 d . . . S3 S 1.2655(4) 0.4442(3) 0.8424(3) 0.0735(19) Uani 1 1 d . . . N1 N 1.1962(12) 0.3795(8) 0.4186(10) 0.060(4) Uani 1 1 d . . . C1 C 0.8911(14) 0.5093(11) 0.3067(12) 0.059(5) Uani 1 1 d . . . C2 C 0.8511(15) 0.5060(10) 0.2123(13) 0.064(6) Uani 1 1 d . . . C3 C 0.9154(16) 0.4652(11) 0.1861(14) 0.072(6) Uani 1 1 d . . . H3 H 0.8999 0.4582 0.1261 0.087 Uiso 1 1 calc R . . C4 C 1.0088(13) 0.4340(10) 0.2592(11) 0.049(4) Uani 1 1 d . . . C5 C 1.0903(16) 0.3889(10) 0.2602(12) 0.058(5) Uani 1 1 d . . . C6 C 1.0816(15) 0.3693(11) 0.1684(12) 0.064(5) Uani 1 1 d . . . C7 C 1.1148(14) 0.4292(11) 0.1240(12) 0.061(5) Uani 1 1 d . . . C8 C 1.1054(15) 0.4064(13) 0.0388(12) 0.065(5) Uani 1 1 d . . . H8 H 1.1296 0.4454 0.0102 0.078 Uiso 1 1 calc R . . C9 C 1.0622(16) 0.3291(13) -0.0022(12) 0.067(5) Uani 1 1 d . . . C10 C 1.0191(19) 0.2718(12) 0.0383(14) 0.089(7) Uani 1 1 d . . . H10 H 0.9830 0.2221 0.0068 0.107 Uiso 1 1 calc R . . C11 C 1.0294(19) 0.2880(12) 0.1235(14) 0.083(7) Uani 1 1 d . . . C12 C 1.1722(17) 0.5143(12) 0.1691(14) 0.082(6) Uani 1 1 d . . . H12A H 1.1315 0.5491 0.1883 0.123 Uiso 1 1 calc R . . H12B H 1.1854 0.5478 0.1270 0.123 Uiso 1 1 calc R . . H12C H 1.2358 0.4994 0.2203 0.123 Uiso 1 1 calc R . . C13 C 1.057(2) 0.3072(15) -0.0921(16) 0.113(9) Uani 1 1 d . . . H13A H 1.0624 0.3607 -0.1205 0.170 Uiso 1 1 calc R . . H13B H 0.9930 0.2787 -0.1298 0.170 Uiso 1 1 calc R . . H13C H 1.1121 0.2680 -0.0832 0.170 Uiso 1 1 calc R . . C14 C 0.9973(15) 0.2242(12) 0.1711(13) 0.070(6) Uani 1 1 d . . . H14A H 0.9675 0.1734 0.1335 0.105 Uiso 1 1 calc R . . H14B H 0.9478 0.2514 0.1853 0.105 Uiso 1 1 calc R . . H14C H 1.0555 0.2061 0.2257 0.105 Uiso 1 1 calc R . . C15 C 1.1845(13) 0.3666(10) 0.3360(12) 0.048(4) Uani 1 1 d . . . C16 C 1.2696(19) 0.3233(12) 0.3353(16) 0.080(6) Uani 1 1 d . . . H16 H 1.2772 0.3093 0.2848 0.096 Uiso 1 1 calc R . . C17 C 1.3370(15) 0.3065(11) 0.4216(15) 0.067(5) Uani 1 1 d . . . H17 H 1.4000 0.2784 0.4434 0.081 Uiso 1 1 calc R . . C18 C 1.2888(14) 0.3420(11) 0.4725(12) 0.057(5) Uani 1 1 d . . . C19 C 1.3386(14) 0.3484(11) 0.5687(13) 0.064(5) Uani 1 1 d . . . C20 C 1.4430(18) 0.3078(13) 0.6253(14) 0.073(6) Uani 1 1 d . . . C21 C 1.450(2) 0.2135(15) 0.6417(13) 0.091(8) Uani 1 1 d . . . C22 C 1.552(2) 0.1838(17) 0.6881(18) 0.110(9) Uani 1 1 d . . . H22 H 1.5580 0.1234 0.7006 0.132 Uiso 1 1 calc R . . C23 C 1.651(2) 0.2295(19) 0.721(2) 0.131(11) Uani 1 1 d . . . C24 C 1.622(2) 0.3218(15) 0.6921(17) 0.107(8) Uani 1 1 d . . . H24 H 1.6754 0.3609 0.7061 0.128 Uiso 1 1 calc R . . C25 C 1.5308(17) 0.3560(14) 0.6502(14) 0.083(7) Uani 1 1 d . . . C26 C 1.3532(17) 0.1586(13) 0.6138(17) 0.098(8) Uani 1 1 d . . . H26A H 1.3715 0.0987 0.6343 0.148 Uiso 1 1 calc R . . H26B H 1.3138 0.1591 0.5495 0.148 Uiso 1 1 calc R . . H26C H 1.3136 0.1835 0.6402 0.148 Uiso 1 1 calc R . . C27 C 1.7448(19) 0.1937(18) 0.7603(19) 0.131(11) Uani 1 1 d . . . H27A H 1.7532 0.1592 0.8113 0.196 Uiso 1 1 calc R . . H27B H 1.7950 0.2401 0.7798 0.196 Uiso 1 1 calc R . . H27C H 1.7535 0.1562 0.7181 0.196 Uiso 1 1 calc R . . C28 C 1.526(2) 0.4582(14) 0.629(2) 0.135(12) Uani 1 1 d . . . H28A H 1.4885 0.4882 0.6545 0.203 Uiso 1 1 calc R . . H28B H 1.4931 0.4670 0.5650 0.203 Uiso 1 1 calc R . . H28C H 1.5943 0.4817 0.6545 0.203 Uiso 1 1 calc R . . C29 C 1.2876(14) 0.3814(11) 0.6174(12) 0.060(5) Uani 1 1 d . . . C30 C 1.3251(16) 0.3814(12) 0.7101(15) 0.072(6) Uani 1 1 d . . . H30 H 1.3868 0.3550 0.7493 0.087 Uiso 1 1 calc R . . C31 C 1.2647(18) 0.4226(11) 0.7382(15) 0.072(6) Uani 1 1 d . . . C32 C 1.1681(15) 0.4514(11) 0.6640(13) 0.057(5) 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 S1 0.074(4) 0.064(3) 0.047(3) 0.002(2) 0.034(3) 0.018(2) S2 0.069(4) 0.067(3) 0.052(3) -0.004(2) 0.034(3) 0.013(2) S3 0.084(4) 0.088(4) 0.049(3) 0.006(2) 0.030(3) 0.029(3) N1 0.087(13) 0.045(8) 0.050(10) -0.011(7) 0.033(9) 0.006(8) C1 0.069(13) 0.053(10) 0.052(13) -0.003(9) 0.027(11) 0.007(9) C2 0.113(17) 0.047(10) 0.070(15) -0.006(9) 0.073(14) 0.008(10) C3 0.091(17) 0.053(10) 0.058(13) -0.002(10) 0.022(13) 0.000(11) C4 0.051(12) 0.069(11) 0.032(10) 0.006(8) 0.025(9) 0.013(9) C5 0.099(16) 0.047(9) 0.065(13) 0.005(9) 0.068(13) 0.018(10) C6 0.095(16) 0.055(11) 0.065(13) -0.003(9) 0.056(12) 0.010(10) C7 0.068(14) 0.068(12) 0.064(13) 0.011(10) 0.045(11) 0.015(10) C8 0.087(15) 0.085(14) 0.042(11) 0.007(11) 0.046(11) 0.014(11) C9 0.101(16) 0.076(13) 0.036(11) -0.009(10) 0.042(11) 0.011(11) C10 0.18(2) 0.061(12) 0.063(14) -0.014(11) 0.086(16) 0.001(13) C11 0.15(2) 0.051(12) 0.073(15) 0.005(11) 0.071(15) 0.026(12) C12 0.122(19) 0.064(12) 0.066(14) -0.011(10) 0.048(13) -0.017(12) C13 0.17(3) 0.111(18) 0.092(19) -0.010(14) 0.093(19) 0.019(17) C14 0.082(15) 0.071(12) 0.090(15) -0.001(11) 0.068(13) -0.012(10) C15 0.045(11) 0.055(10) 0.056(13) -0.011(9) 0.034(10) 0.009(8) C16 0.118(19) 0.055(11) 0.082(18) -0.013(11) 0.059(16) 0.001(12) C17 0.064(13) 0.066(12) 0.067(15) 0.006(10) 0.028(12) 0.020(10) C18 0.068(13) 0.065(11) 0.052(12) 0.016(9) 0.041(11) 0.036(10) C19 0.067(13) 0.063(11) 0.066(14) 0.025(10) 0.033(11) 0.040(10) C20 0.095(18) 0.067(13) 0.077(15) -0.011(11) 0.058(14) 0.003(12) C21 0.11(2) 0.088(16) 0.051(14) 0.015(11) 0.022(13) 0.050(15) C22 0.12(2) 0.099(18) 0.10(2) 0.006(15) 0.050(18) 0.059(18) C23 0.12(3) 0.11(2) 0.11(2) -0.054(19) 0.02(2) -0.03(2) C24 0.082(18) 0.077(16) 0.12(2) 0.000(14) 0.010(16) 0.011(14) C25 0.047(14) 0.080(15) 0.085(16) -0.016(12) -0.001(12) 0.010(13) C26 0.074(16) 0.073(14) 0.12(2) 0.002(13) 0.025(14) -0.025(12) C27 0.068(18) 0.13(2) 0.14(3) 0.027(18) 0.008(16) 0.072(16) C28 0.14(3) 0.064(15) 0.14(3) 0.017(15) 0.011(19) -0.018(14) C29 0.080(14) 0.059(11) 0.042(12) 0.002(9) 0.030(11) 0.007(10) C30 0.071(14) 0.068(12) 0.080(16) -0.005(11) 0.038(12) 0.006(10) C31 0.102(18) 0.055(11) 0.098(17) -0.005(11) 0.079(16) 0.014(11) C32 0.060(13) 0.063(11) 0.059(13) 0.009(9) 0.038(11) 0.027(10) _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 S1 C1 1.725(19) . ? S1 C4 1.791(15) . ? S2 C29 1.696(19) . ? S2 C32 1.709(18) . ? S3 C2 1.70(2) 3_766 ? S3 C31 1.774(19) . ? N1 C15 1.33(2) . ? N1 C18 1.36(2) . ? C1 C32 1.33(2) 3_766 ? C1 C2 1.41(2) . ? C2 C3 1.36(2) . ? C2 S3 1.70(2) 3_766 ? C3 C4 1.43(2) . ? C3 H3 0.9300 . ? C4 C5 1.38(2) . ? C5 C15 1.42(2) . ? C5 C6 1.52(2) . ? C6 C7 1.40(2) . ? C6 C11 1.46(3) . ? C7 C8 1.41(2) . ? C7 C12 1.53(2) . ? C8 C9 1.35(3) . ? C8 H8 0.9300 . ? C9 C10 1.42(3) . ? C9 C13 1.51(3) . ? C10 C11 1.39(3) . ? C10 H10 0.9300 . ? C11 C14 1.46(2) . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? C15 C16 1.42(3) . ? C16 C17 1.35(3) . ? C16 H16 0.9300 . ? C17 C18 1.45(2) . ? C17 H17 0.9300 . ? C18 C19 1.43(2) . ? C19 C29 1.43(2) . ? C19 C20 1.52(3) . ? C20 C25 1.37(3) . ? C20 C21 1.44(3) . ? C21 C22 1.41(3) . ? C21 C26 1.53(3) . ? C22 C23 1.47(4) . ? C22 H22 0.9300 . ? C23 C27 1.35(3) . ? C23 C24 1.47(4) . ? C24 C25 1.30(3) . ? C24 H24 0.9300 . ? C25 C28 1.58(3) . ? C26 H26A 0.9600 . ? C26 H26B 0.9600 . ? C26 H26C 0.9600 . ? C27 H27A 0.9600 . ? C27 H27B 0.9600 . ? C27 H27C 0.9600 . ? C28 H28A 0.9600 . ? C28 H28B 0.9600 . ? C28 H28C 0.9600 . ? C29 C30 1.39(2) . ? C30 C31 1.34(2) . ? C30 H30 0.9300 . ? C31 C32 1.46(3) . ? C32 C1 1.33(2) 3_766 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 S1 C4 90.6(8) . . ? C29 S2 C32 93.3(9) . . ? C2 S3 C31 90.5(9) 3_766 . ? C15 N1 C18 103.6(14) . . ? C32 C1 C2 115.3(17) 3_766 . ? C32 C1 S1 131.5(16) 3_766 . ? C2 C1 S1 113.2(13) . . ? C3 C2 C1 112.7(18) . . ? C3 C2 S3 135.0(16) . 3_766 ? C1 C2 S3 112.4(12) . 3_766 ? C2 C3 C4 114.3(18) . . ? C2 C3 H3 122.9 . . ? C4 C3 H3 122.9 . . ? C5 C4 C3 131.5(16) . . ? C5 C4 S1 119.2(13) . . ? C3 C4 S1 109.3(12) . . ? C4 C5 C15 128.0(15) . . ? C4 C5 C6 115.1(17) . . ? C15 C5 C6 116.6(15) . . ? C7 C6 C11 120.1(16) . . ? C7 C6 C5 122.1(16) . . ? C11 C6 C5 117.7(15) . . ? C6 C7 C8 119.2(17) . . ? C6 C7 C12 122.0(16) . . ? C8 C7 C12 118.4(16) . . ? C9 C8 C7 121.7(17) . . ? C9 C8 H8 119.2 . . ? C7 C8 H8 119.2 . . ? C8 C9 C10 119.4(15) . . ? C8 C9 C13 119.3(18) . . ? C10 C9 C13 121.2(19) . . ? C11 C10 C9 121.8(19) . . ? C11 C10 H10 119.1 . . ? C9 C10 H10 119.1 . . ? C10 C11 C6 117.3(17) . . ? C10 C11 C14 122.6(18) . . ? C6 C11 C14 119.9(17) . . ? C7 C12 H12A 109.5 . . ? C7 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C7 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C9 C13 H13A 109.5 . . ? C9 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C9 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C11 C14 H14A 109.5 . . ? C11 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C11 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? N1 C15 C16 112.9(17) . . ? N1 C15 C5 119.7(14) . . ? C16 C15 C5 127.2(16) . . ? C17 C16 C15 107.1(18) . . ? C17 C16 H16 126.4 . . ? C15 C16 H16 126.4 . . ? C16 C17 C18 104.1(17) . . ? C16 C17 H17 128.0 . . ? C18 C17 H17 128.0 . . ? N1 C18 C19 123.5(14) . . ? N1 C18 C17 112.3(16) . . ? C19 C18 C17 123.7(17) . . ? C18 C19 C29 122.3(16) . . ? C18 C19 C20 121.3(15) . . ? C29 C19 C20 115.8(16) . . ? C25 C20 C21 119(2) . . ? C25 C20 C19 121.3(18) . . ? C21 C20 C19 119(2) . . ? C22 C21 C20 112(2) . . ? C22 C21 C26 127(2) . . ? C20 C21 C26 120(2) . . ? C21 C22 C23 133(2) . . ? C21 C22 H22 113.6 . . ? C23 C22 H22 113.6 . . ? C27 C23 C24 128(3) . . ? C27 C23 C22 128(3) . . ? C24 C23 C22 103(3) . . ? C25 C24 C23 129(3) . . ? C25 C24 H24 115.6 . . ? C23 C24 H24 115.6 . . ? C24 C25 C20 123(2) . . ? C24 C25 C28 116(2) . . ? C20 C25 C28 121(2) . . ? C21 C26 H26A 109.5 . . ? C21 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C21 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C23 C27 H27A 109.5 . . ? C23 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C23 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? C25 C28 H28A 109.5 . . ? C25 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C25 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? C30 C29 C19 126.6(17) . . ? C30 C29 S2 111.1(14) . . ? C19 C29 S2 122.2(14) . . ? C31 C30 C29 114(2) . . ? C31 C30 H30 122.9 . . ? C29 C30 H30 122.9 . . ? C30 C31 C32 112.7(19) . . ? C30 C31 S3 137.0(19) . . ? C32 C31 S3 110.0(12) . . ? C1 C32 C31 111.8(17) 3_766 . ? C1 C32 S2 139.6(16) 3_766 . ? C31 C32 S2 108.3(12) . . ? _diffrn_measured_fraction_theta_max 0.963 _diffrn_reflns_theta_full 21.96 _diffrn_measured_fraction_theta_full 0.963 _refine_diff_density_max 1.902 _refine_diff_density_min -1.202 _refine_diff_density_rms 0.312 loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 0.500 1.000 0.500 445 379 ' ' 2 0.500 0.500 0.000 445 374 ' ' _platon_squeeze_details ; ; # Attachment '694221-corrected.cif' data_sse _database_code_depnum_ccdc_archive 'CCDC 694221' #TrackingRef '694221-corrected.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common Rubyrin-sse _chemical_melting_point ? _chemical_formula_moiety 'C64 H52 N2 S3 Se2' _chemical_formula_sum 'C64 H52 N2 S4.60 Se0.40' _chemical_formula_weight 1028.18 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Se Se -0.0929 2.2259 '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 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 15.0818(30) _cell_length_b 15.1228(30) _cell_length_c 16.1830(32) _cell_angle_alpha 90.00 _cell_angle_beta 114.696(30) _cell_angle_gamma 90.00 _cell_volume 3353.4(14) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description parallelopiped _exptl_crystal_colour green _exptl_crystal_size_max .2 _exptl_crystal_size_mid .2 _exptl_crystal_size_min .2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.018 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1074.4 _exptl_absorpt_coefficient_mu 0.411 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.7092 _exptl_absorpt_correction_T_max 0.7092 _exptl_absorpt_process_details SADABS _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 31858 _diffrn_reflns_av_R_equivalents 0.0512 _diffrn_reflns_av_sigmaI/netI 0.0487 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.97 _diffrn_reflns_theta_max 25.68 _reflns_number_total 6366 _reflns_number_gt 4030 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'BRUKER SMART' _computing_cell_refinement 'BRUKER SMART' _computing_data_reduction 'BRUKER SMART' _computing_structure_solution "'BRUKER SHELXTL" _computing_structure_refinement 'BRUKER SHELXTL' _computing_molecular_graphics 'BRUKER SHELXTL' _computing_publication_material 'BRUKER SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. The difmap phased on the non-hydrogen atoms of the complex molecule showed two regions centered at (0,0.5,0) and (0.5,1,0.5) respectively, containing peaks due to severely disordered solvent. No consistent models for dichloromethane or hexane molecules could be assembled from these peaks. This part of the structure was modeled by using the SQUEEZE procedure of PLATON (Spek, 1995). A new set of F2 (hkl) values with the contribution from solvent molecules withdrawn was obtained by the SQUEEZE and refined further ; _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^)+(0.2000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6120 _refine_ls_number_parameters 329 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1633 _refine_ls_R_factor_gt 0.1251 _refine_ls_wR_factor_ref 0.3887 _refine_ls_wR_factor_gt 0.3594 _refine_ls_goodness_of_fit_ref 1.503 _refine_ls_restrained_S_all 1.503 _refine_ls_shift/su_max 0.002 _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 S1 S 0.35829(15) 0.97129(15) 0.85580(13) 0.0458(8) Uiso 0.90 1 d P . . S2 S 0.40770(14) 0.92611(14) 1.07844(12) 0.0467(7) Uiso 0.90 1 d P . . S3 S 0.4196(3) 1.0577(3) 0.6541(3) 0.0974(13) Uani 0.50 1 d P . . Se1 Se 0.3685(4) 0.9517(5) 0.8590(4) 0.0305(19) Uiso 0.10 1 d P . . Se2 Se 0.3937(4) 0.9473(4) 1.0736(3) 0.0223(14) Uiso 0.10 1 d P . . N1 N 0.2271(4) 0.8817(4) 0.9231(4) 0.0770(15) Uani 1 1 d . . . C1 C 0.4973(6) 0.9474(6) 1.1826(9) 0.109(3) Uani 1 1 d . . . C2 C 0.4753(9) 0.9158(8) 1.2506(8) 0.124(3) Uani 1 1 d . . . C3 C 0.3804(7) 0.8760(6) 1.2179(5) 0.098(2) Uani 1 1 d . . . H3 H 0.3544 0.8515 1.2557 0.118 Uiso 1 1 calc R . . C4 C 0.3313(6) 0.8778(5) 1.1233(5) 0.088(2) Uani 1 1 d . . . C5 C 0.2361(6) 0.8454(6) 1.0730(5) 0.088(2) Uani 1 1 d . . . C6 C 0.1827(6) 0.8023(6) 1.1247(6) 0.090(2) Uani 1 1 d . . . C7 C 0.1218(8) 0.8561(6) 1.1486(8) 0.117(3) Uani 1 1 d . . . C8 C 0.0760(9) 0.8143(8) 1.1990(9) 0.136(4) Uani 1 1 d . . . H8 H 0.0389 0.8499 1.2193 0.163 Uiso 1 1 calc R . . C9 C 0.0814(9) 0.7294(8) 1.2197(8) 0.126(4) Uani 1 1 d . . . C10 C 0.1448(9) 0.6778(7) 1.1940(7) 0.122(3) Uani 1 1 d . . . H10 H 0.1519 0.6179 1.2083 0.147 Uiso 1 1 calc R . . C11 C 0.1967(7) 0.7141(7) 1.1482(7) 0.105(3) Uani 1 1 d . . . C12 C 0.1095(14) 0.9522(9) 1.1298(15) 0.223(10) Uani 1 1 d . . . H12A H 0.1725 0.9800 1.1521 0.334 Uiso 1 1 calc R . . H12B H 0.0722 0.9773 1.1596 0.334 Uiso 1 1 calc R . . H12C H 0.0759 0.9617 1.0654 0.334 Uiso 1 1 calc R . . C13 C 0.0324(13) 0.6850(10) 1.2703(12) 0.196(7) Uani 1 1 d . . . H13A H 0.0551 0.7099 1.3302 0.294 Uiso 1 1 calc R . . H13B H 0.0471 0.6230 1.2748 0.294 Uiso 1 1 calc R . . H13C H -0.0369 0.6934 1.2389 0.294 Uiso 1 1 calc R . . C14 C 0.2567(10) 0.6550(9) 1.1233(12) 0.183(6) Uani 1 1 d . . . H14A H 0.2337 0.6540 1.0583 0.275 Uiso 1 1 calc R . . H14B H 0.2531 0.5965 1.1447 0.275 Uiso 1 1 calc R . . H14C H 0.3231 0.6751 1.1503 0.275 Uiso 1 1 calc R . . C15 C 0.1908(5) 0.8435(5) 0.9788(5) 0.082(2) Uani 1 1 d . . . C16 C 0.0937(6) 0.8077(6) 0.9238(6) 0.100(3) Uani 1 1 d . . . H16 H 0.0524 0.7805 0.9455 0.120 Uiso 1 1 calc R . . C17 C 0.0757(6) 0.8211(6) 0.8385(6) 0.097(2) Uani 1 1 d . . . H17 H 0.0197 0.8043 0.7882 0.116 Uiso 1 1 calc R . . C18 C 0.1579(5) 0.8663(5) 0.8367(5) 0.0776(19) Uani 1 1 d . . . C19 C 0.1697(5) 0.8917(5) 0.7561(5) 0.0796(19) Uani 1 1 d . . . C20 C 0.0889(5) 0.8699(5) 0.6664(5) 0.0742(18) Uani 1 1 d . . . C21 C 0.0941(6) 0.7905(6) 0.6240(6) 0.094(2) Uani 1 1 d . . . C22 C 0.0208(5) 0.7712(6) 0.5371(6) 0.093(2) Uani 1 1 d . . . H22 H 0.0250 0.7197 0.5076 0.111 Uiso 1 1 calc R . . C23 C -0.0565(6) 0.8271(6) 0.4957(5) 0.091(2) Uani 1 1 d . . . C24 C -0.0597(6) 0.9070(6) 0.5397(6) 0.098(2) Uani 1 1 d . . . H24 H -0.1101 0.9469 0.5106 0.117 Uiso 1 1 calc R . . C25 C 0.0108(6) 0.9268(5) 0.6252(6) 0.089(2) Uani 1 1 d . . . C26 C 0.1776(7) 0.7253(7) 0.6687(8) 0.127(4) Uani 1 1 d . . . H26A H 0.2292 0.7533 0.7191 0.191 Uiso 1 1 calc R . . H26B H 0.2016 0.7066 0.6252 0.191 Uiso 1 1 calc R . . H26C H 0.1544 0.6749 0.6899 0.191 Uiso 1 1 calc R . . C27 C -0.1401(6) 0.8061(8) 0.4038(6) 0.123(3) Uani 1 1 d . . . H27A H -0.1188 0.7633 0.3723 0.184 Uiso 1 1 calc R . . H27B H -0.1598 0.8592 0.3682 0.184 Uiso 1 1 calc R . . H27C H -0.1944 0.7828 0.4133 0.184 Uiso 1 1 calc R . . C28 C 0.0053(8) 1.0124(7) 0.6708(7) 0.127(4) Uani 1 1 d . . . H28A H -0.0031 0.9998 0.7252 0.191 Uiso 1 1 calc R . . H28B H -0.0490 1.0467 0.6301 0.191 Uiso 1 1 calc R . . H28C H 0.0646 1.0452 0.6860 0.191 Uiso 1 1 calc R . . C29 C 0.2520(6) 0.9352(5) 0.7565(5) 0.0779(19) Uani 1 1 d . . . C30 C 0.2631(6) 0.9642(5) 0.6785(6) 0.089(2) Uani 1 1 d . . . H30 H 0.2161 0.9545 0.6198 0.107 Uiso 1 1 calc R . . C31 C 0.3486(7) 1.0079(6) 0.6963(8) 0.102(3) Uani 1 1 d . . . C32 C 0.4110(6) 1.0126(6) 0.7885(8) 0.113(3) 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 S3 0.093(3) 0.138(4) 0.055(2) 0.010(2) 0.0258(19) -0.029(2) N1 0.071(4) 0.093(4) 0.066(3) -0.002(3) 0.029(3) -0.010(3) C1 0.069(5) 0.096(6) 0.154(10) -0.020(6) 0.040(6) -0.009(4) C2 0.126(9) 0.127(8) 0.101(8) -0.016(6) 0.029(6) 0.010(7) C3 0.106(6) 0.121(7) 0.070(5) -0.007(4) 0.039(4) -0.025(5) C4 0.085(5) 0.096(5) 0.080(5) -0.004(4) 0.033(4) -0.012(4) C5 0.090(5) 0.102(6) 0.075(5) 0.002(4) 0.038(4) -0.015(4) C6 0.107(6) 0.096(6) 0.086(5) -0.007(4) 0.059(5) -0.016(4) C7 0.151(9) 0.095(6) 0.153(9) 0.003(6) 0.110(8) -0.015(6) C8 0.150(9) 0.139(10) 0.161(11) -0.010(8) 0.107(9) -0.020(7) C9 0.145(9) 0.108(8) 0.159(10) -0.011(7) 0.098(8) -0.045(7) C10 0.152(9) 0.114(7) 0.113(8) 0.021(6) 0.067(7) -0.018(7) C11 0.118(7) 0.104(7) 0.112(7) -0.001(5) 0.067(6) -0.017(5) C12 0.257(19) 0.123(10) 0.39(3) 0.043(13) 0.23(2) 0.058(11) C13 0.270(18) 0.186(13) 0.217(16) -0.007(11) 0.187(16) -0.057(12) C14 0.182(13) 0.133(10) 0.29(2) 0.002(11) 0.150(14) 0.031(9) C15 0.077(5) 0.106(5) 0.066(4) -0.002(4) 0.035(4) -0.017(4) C16 0.091(6) 0.133(7) 0.087(6) -0.010(5) 0.047(5) -0.044(5) C17 0.081(5) 0.119(6) 0.081(5) -0.013(5) 0.024(4) -0.030(5) C18 0.076(4) 0.082(4) 0.069(4) -0.004(3) 0.025(3) -0.011(4) C19 0.077(5) 0.084(5) 0.077(5) -0.005(4) 0.032(4) -0.020(4) C20 0.073(4) 0.085(5) 0.064(4) 0.006(3) 0.029(3) -0.004(4) C21 0.086(5) 0.091(5) 0.085(5) -0.010(4) 0.015(4) -0.010(4) C22 0.082(5) 0.107(6) 0.082(5) -0.006(4) 0.028(4) -0.019(4) C23 0.083(5) 0.103(6) 0.069(5) -0.001(4) 0.016(4) -0.019(4) C24 0.081(5) 0.106(6) 0.082(5) 0.003(5) 0.011(4) -0.004(4) C25 0.079(5) 0.094(6) 0.089(5) -0.004(4) 0.029(4) -0.003(4) C26 0.100(6) 0.103(7) 0.145(9) -0.015(6) 0.017(6) 0.018(5) C27 0.085(6) 0.175(10) 0.088(6) -0.007(6) 0.017(5) -0.023(6) C28 0.128(8) 0.133(8) 0.107(8) -0.030(6) 0.036(6) 0.011(6) C29 0.084(5) 0.090(5) 0.064(4) 0.002(3) 0.034(4) -0.012(4) C30 0.081(5) 0.106(6) 0.077(5) -0.002(4) 0.028(4) -0.010(4) C31 0.091(6) 0.104(6) 0.127(8) -0.002(5) 0.060(6) -0.016(5) C32 0.071(5) 0.114(7) 0.149(10) -0.029(6) 0.041(6) -0.020(5) _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 S1 C32 1.713(11) . ? S1 C29 1.816(8) . ? S2 C1 1.693(11) . ? S2 C4 1.757(8) . ? S3 C31 1.671(10) . ? S3 C2 1.735(12) 3_677 ? Se1 C32 1.781(13) . ? Se1 C29 1.861(10) . ? Se2 C1 1.802(12) . ? Se2 C4 1.808(9) . ? N1 C15 1.364(9) . ? N1 C18 1.371(8) . ? C1 C2 1.361(16) . ? C1 C32 1.399(12) 3_677 ? C2 C3 1.435(15) . ? C2 S3 1.735(12) 3_677 ? C3 C4 1.395(11) . ? C4 C5 1.409(11) . ? C5 C15 1.386(10) . ? C5 C6 1.529(10) . ? C6 C11 1.379(12) . ? C6 C7 1.396(12) . ? C7 C8 1.418(13) . ? C7 C12 1.481(16) . ? C8 C9 1.321(15) . ? C9 C10 1.423(14) . ? C9 C13 1.475(14) . ? C10 C11 1.396(12) . ? C11 C14 1.443(14) . ? C15 C16 1.463(10) . ? C16 C17 1.307(11) . ? C17 C18 1.427(10) . ? C18 C19 1.441(10) . ? C19 C29 1.402(10) . ? C19 C20 1.490(9) . ? C20 C25 1.385(10) . ? C20 C21 1.401(11) . ? C21 C22 1.409(10) . ? C21 C26 1.523(12) . ? C22 C23 1.368(11) . ? C23 C24 1.413(12) . ? C23 C27 1.527(11) . ? C24 C25 1.380(11) . ? C25 C28 1.509(12) . ? C29 C30 1.411(11) . ? C30 C31 1.368(12) . ? C31 C32 1.393(14) . ? C32 C1 1.399(12) 3_677 ? 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 C32 S1 C29 91.1(4) . . ? C1 S2 C4 93.2(5) . . ? C31 S3 C2 104.1(7) . 3_677 ? C32 Se1 C29 87.6(5) . . ? C1 Se2 C4 88.0(5) . . ? C15 N1 C18 104.9(6) . . ? C2 C1 C32 114.9(12) . 3_677 ? C2 C1 S2 112.1(8) . . ? C32 C1 S2 133.0(11) 3_677 . ? C2 C1 Se2 112.8(8) . . ? C32 C1 Se2 131.2(11) 3_677 . ? S2 C1 Se2 11.7(2) . . ? C1 C2 C3 113.1(10) . . ? C1 C2 S3 101.4(10) . 3_677 ? C3 C2 S3 145.5(11) . 3_677 ? C4 C3 C2 112.7(9) . . ? C3 C4 C5 124.9(8) . . ? C3 C4 S2 108.8(6) . . ? C5 C4 S2 126.3(6) . . ? C3 C4 Se2 111.3(6) . . ? C5 C4 Se2 122.7(6) . . ? S2 C4 Se2 11.89(19) . . ? C15 C5 C4 123.9(7) . . ? C15 C5 C6 117.5(7) . . ? C4 C5 C6 118.4(7) . . ? C11 C6 C7 122.0(8) . . ? C11 C6 C5 120.5(8) . . ? C7 C6 C5 117.5(8) . . ? C6 C7 C8 115.8(9) . . ? C6 C7 C12 123.7(9) . . ? C8 C7 C12 120.4(10) . . ? C9 C8 C7 125.8(11) . . ? C8 C9 C10 115.9(9) . . ? C8 C9 C13 126.2(12) . . ? C10 C9 C13 117.8(11) . . ? C11 C10 C9 122.3(9) . . ? C6 C11 C10 118.1(9) . . ? C6 C11 C14 124.4(9) . . ? C10 C11 C14 117.4(10) . . ? N1 C15 C5 124.6(7) . . ? N1 C15 C16 109.3(6) . . ? C5 C15 C16 125.8(7) . . ? C17 C16 C15 107.4(7) . . ? C16 C17 C18 107.2(7) . . ? N1 C18 C17 111.1(6) . . ? N1 C18 C19 123.3(6) . . ? C17 C18 C19 125.7(7) . . ? C29 C19 C18 124.3(7) . . ? C29 C19 C20 118.1(6) . . ? C18 C19 C20 117.6(6) . . ? C25 C20 C21 120.5(7) . . ? C25 C20 C19 121.0(7) . . ? C21 C20 C19 118.5(7) . . ? C20 C21 C22 119.0(8) . . ? C20 C21 C26 121.8(7) . . ? C22 C21 C26 119.2(8) . . ? C23 C22 C21 120.9(8) . . ? C22 C23 C24 118.9(7) . . ? C22 C23 C27 122.4(8) . . ? C24 C23 C27 118.7(8) . . ? C25 C24 C23 121.1(8) . . ? C24 C25 C20 119.4(8) . . ? C24 C25 C28 120.0(8) . . ? C20 C25 C28 120.5(8) . . ? C19 C29 C30 125.2(7) . . ? C19 C29 S1 126.7(6) . . ? C30 C29 S1 107.9(6) . . ? C19 C29 Se1 124.9(6) . . ? C30 C29 Se1 109.5(6) . . ? S1 C29 Se1 10.1(2) . . ? C31 C30 C29 114.5(8) . . ? C30 C31 C32 114.0(9) . . ? C30 C31 S3 147.1(9) . . ? C32 C31 S3 98.8(7) . . ? C31 C32 C1 120.8(11) . 3_677 ? C31 C32 S1 112.1(6) . . ? C1 C32 S1 127.0(10) 3_677 . ? C31 C32 Se1 113.3(7) . . ? C1 C32 Se1 125.4(10) 3_677 . ? S1 C32 Se1 10.5(2) . . ? _diffrn_measured_fraction_theta_max 0.961 _diffrn_reflns_theta_full 25.68 _diffrn_measured_fraction_theta_full 0.961 _refine_diff_density_max 1.183 _refine_diff_density_min -0.562 _refine_diff_density_rms 0.153 loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 0.000 0.500 0.000 443 53 ' ' 2 0.500 1.000 0.500 443 53 ' ' _platon_squeeze_details ; ;