# Electronic Supplementary Material (ESI) for RSC Advances # 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_accn1_0m #TrackingRef 'web_deposit_cif_file_0_ansumanbej_1362978648.3b.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C35 H23 N' _chemical_formula_weight 457.54 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' _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 6.6655(8) _cell_length_b 21.962(2) _cell_length_c 32.777(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 4798.2(9) _cell_formula_units_Z 8 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 6470 _cell_measurement_theta_min 2.23 _cell_measurement_theta_max 24.33 _exptl_crystal_description BLOCK _exptl_crystal_colour COLORLESS _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.267 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1920 _exptl_absorpt_coefficient_mu 0.073 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.9885 _exptl_absorpt_correction_T_max 0.9942 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 40482 _diffrn_reflns_av_R_equivalents 0.0533 _diffrn_reflns_av_sigmaI/netI 0.0253 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_l_min -38 _diffrn_reflns_limit_l_max 38 _diffrn_reflns_theta_min 1.85 _diffrn_reflns_theta_max 24.58 _reflns_number_total 4015 _reflns_number_gt 3286 _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, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'MERCURY 2.3' _computing_publication_material 'ORTEP 3V.2' _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^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4015 _refine_ls_number_parameters 325 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0580 _refine_ls_R_factor_gt 0.0453 _refine_ls_wR_factor_ref 0.1479 _refine_ls_wR_factor_gt 0.1389 _refine_ls_goodness_of_fit_ref 1.102 _refine_ls_restrained_S_all 1.102 _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 N1 N 0.0890(2) 0.14328(8) 0.34778(5) 0.0388(4) Uani 1 1 d . . . C3 C 0.0801(2) 0.16043(8) 0.24215(5) 0.0274(4) Uani 1 1 d . . . H3 H 0.0881 0.2009 0.2503 0.033 Uiso 1 1 calc R . . C4 C 0.0782(2) 0.14604(8) 0.20012(5) 0.0246(4) Uani 1 1 d . . . C5 C 0.0642(2) 0.08415(8) 0.18834(5) 0.0253(4) Uani 1 1 d . . . C22 C 0.1053(2) 0.17593(8) 0.12914(5) 0.0262(4) Uani 1 1 d . . . C2 C 0.0703(2) 0.11556(8) 0.27110(5) 0.0279(4) Uani 1 1 d . . . C8 C 0.0714(2) 0.06868(8) 0.14620(5) 0.0251(4) Uani 1 1 d . . . C15 C 0.1015(2) 0.11364(8) 0.11753(5) 0.0257(4) Uani 1 1 d . . . C29 C 0.0926(2) 0.19238(8) 0.16959(5) 0.0256(4) Uani 1 1 d . . . C30 C 0.1011(3) 0.25739(8) 0.18223(5) 0.0283(4) Uani 1 1 d . . . C16 C 0.1321(3) 0.09724(8) 0.07385(5) 0.0286(4) Uani 1 1 d . . . C9 C 0.0381(3) 0.00395(8) 0.13331(5) 0.0280(4) Uani 1 1 d . . . C6 C 0.0483(3) 0.03921(8) 0.21921(5) 0.0280(4) Uani 1 1 d . . . H6 H 0.0345 -0.0014 0.2118 0.034 Uiso 1 1 calc R . . C1 C 0.0794(3) 0.13112(8) 0.31377(6) 0.0295(4) Uani 1 1 d . . . C26 C 0.1229(3) 0.30392(9) 0.03106(6) 0.0378(5) Uani 1 1 d . . . H26 H 0.1252 0.3307 0.0091 0.045 Uiso 1 1 calc R . . C7 C 0.0529(3) 0.05413(8) 0.25949(5) 0.0293(4) Uani 1 1 d . . . H7 H 0.0445 0.0239 0.2793 0.035 Uiso 1 1 calc R . . C23 C 0.1156(3) 0.22289(8) 0.09614(5) 0.0267(4) Uani 1 1 d . . . C24 C 0.2936(3) 0.23425(8) 0.07534(5) 0.0304(4) Uani 1 1 d . . . H24 H 0.4109 0.2146 0.0832 0.037 Uiso 1 1 calc R . . C31 C 0.2834(3) 0.28699(8) 0.18587(5) 0.0360(5) Uani 1 1 d . . . H31 H 0.4012 0.2661 0.1800 0.043 Uiso 1 1 calc R . . C27 C -0.0540(3) 0.29352(9) 0.05177(6) 0.0367(5) Uani 1 1 d . . . H27 H -0.1709 0.3134 0.0439 0.044 Uiso 1 1 calc R . . C13 C 0.1569(3) -0.09219(9) 0.10814(6) 0.0404(5) Uani 1 1 d . . . H13 H 0.2621 -0.1168 0.0995 0.048 Uiso 1 1 calc R . . C10 C -0.1554(3) -0.01924(8) 0.13332(5) 0.0337(4) Uani 1 1 d . . . H10 H -0.2612 0.0053 0.1418 0.040 Uiso 1 1 calc R . . C35 C -0.0732(3) 0.28940(9) 0.19100(6) 0.0382(5) Uani 1 1 d . . . H35 H -0.1973 0.2704 0.1888 0.046 Uiso 1 1 calc R . . C12 C -0.0363(3) -0.11459(9) 0.10842(6) 0.0381(5) Uani 1 1 d . . . H12 H -0.0610 -0.1544 0.1001 0.046 Uiso 1 1 calc R . . C14 C 0.1941(3) -0.03342(8) 0.12072(5) 0.0341(4) Uani 1 1 d . . . H14 H 0.3249 -0.0187 0.1208 0.041 Uiso 1 1 calc R . . C28 C -0.0571(3) 0.25331(9) 0.08438(5) 0.0325(4) Uani 1 1 d . . . H28 H -0.1761 0.2467 0.0985 0.039 Uiso 1 1 calc R . . C20 C 0.0102(4) 0.08075(9) 0.00573(6) 0.0428(5) Uani 1 1 d . . . H20 H -0.0954 0.0802 -0.0128 0.051 Uiso 1 1 calc R . . C19 C 0.2012(4) 0.06578(8) -0.00699(6) 0.0436(5) Uani 1 1 d . . . H19 H 0.2237 0.0549 -0.0340 0.052 Uiso 1 1 calc R . . C21 C -0.0246(3) 0.09662(8) 0.04596(6) 0.0360(5) Uani 1 1 d . . . H21 H -0.1535 0.1069 0.0544 0.043 Uiso 1 1 calc R . . C11 C -0.1933(3) -0.07811(9) 0.12098(6) 0.0386(5) Uani 1 1 d . . . H11 H -0.3238 -0.0932 0.1211 0.046 Uiso 1 1 calc R . . C18 C 0.3586(3) 0.06680(8) 0.02015(6) 0.0403(5) Uani 1 1 d . . . H18 H 0.4874 0.0570 0.0115 0.048 Uiso 1 1 calc R . . C25 C 0.2969(3) 0.27461(8) 0.04301(5) 0.0352(5) Uani 1 1 d . . . H25 H 0.4164 0.2821 0.0292 0.042 Uiso 1 1 calc R . . C33 C 0.1199(4) 0.37855(9) 0.20668(6) 0.0439(5) Uani 1 1 d . . . H33 H 0.1261 0.4190 0.2149 0.053 Uiso 1 1 calc R . . C17 C 0.3243(3) 0.08254(8) 0.06047(5) 0.0336(4) Uani 1 1 d . . . H17 H 0.4308 0.0833 0.0788 0.040 Uiso 1 1 calc R . . C34 C -0.0619(3) 0.34989(10) 0.20304(6) 0.0452(5) Uani 1 1 d . . . H34 H -0.1791 0.3712 0.2087 0.054 Uiso 1 1 calc R . . C32 C 0.2933(4) 0.34698(9) 0.19806(6) 0.0449(5) Uani 1 1 d . . . H32 H 0.4172 0.3661 0.2005 0.054 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0325(9) 0.0535(11) 0.0303(10) -0.0023(8) 0.0013(7) 0.0047(7) C3 0.0191(9) 0.0344(10) 0.0286(10) -0.0030(7) 0.0008(7) 0.0014(7) C4 0.0155(9) 0.0343(10) 0.0241(9) 0.0004(7) -0.0011(6) 0.0006(7) C5 0.0164(9) 0.0340(10) 0.0255(9) 0.0026(7) 0.0002(7) 0.0015(7) C22 0.0199(9) 0.0336(10) 0.0251(9) 0.0013(7) -0.0003(7) -0.0003(7) C2 0.0168(9) 0.0425(11) 0.0245(9) 0.0022(8) 0.0013(7) 0.0020(7) C8 0.0203(9) 0.0302(9) 0.0247(9) -0.0001(7) -0.0006(7) 0.0001(7) C15 0.0216(9) 0.0314(10) 0.0240(9) -0.0015(7) -0.0018(7) 0.0003(7) C29 0.0187(9) 0.0316(9) 0.0264(9) 0.0002(7) -0.0007(7) 0.0007(7) C30 0.0300(10) 0.0345(10) 0.0204(9) 0.0031(7) -0.0004(7) 0.0029(8) C16 0.0347(11) 0.0258(9) 0.0253(9) 0.0012(7) 0.0017(7) -0.0023(8) C9 0.0308(10) 0.0323(10) 0.0210(9) 0.0031(7) -0.0022(7) -0.0004(8) C6 0.0228(9) 0.0309(9) 0.0303(10) 0.0014(7) -0.0019(7) -0.0003(7) C1 0.0228(10) 0.0373(10) 0.0283(11) 0.0034(8) 0.0017(7) 0.0023(8) C26 0.0531(13) 0.0315(10) 0.0289(10) 0.0010(8) -0.0003(9) -0.0020(9) C7 0.0222(9) 0.0385(10) 0.0273(10) 0.0063(8) 0.0002(7) 0.0011(7) C23 0.0301(10) 0.0263(9) 0.0236(9) -0.0039(7) -0.0020(7) -0.0014(7) C24 0.0316(10) 0.0308(10) 0.0289(9) -0.0015(7) 0.0003(7) -0.0001(8) C31 0.0340(11) 0.0372(11) 0.0369(11) -0.0027(8) 0.0019(8) 0.0005(9) C27 0.0386(12) 0.0364(10) 0.0351(11) 0.0018(8) -0.0055(8) 0.0041(8) C13 0.0456(13) 0.0369(11) 0.0385(11) -0.0034(9) 0.0003(9) 0.0069(9) C10 0.0328(11) 0.0363(10) 0.0320(10) -0.0010(8) 0.0005(8) 0.0007(8) C35 0.0332(11) 0.0426(12) 0.0387(11) -0.0015(9) 0.0004(8) 0.0054(9) C12 0.0505(13) 0.0327(10) 0.0310(10) -0.0020(8) -0.0051(9) -0.0050(9) C14 0.0335(11) 0.0362(11) 0.0325(10) 0.0016(8) -0.0004(8) 0.0009(8) C28 0.0317(10) 0.0356(10) 0.0302(10) -0.0003(8) 0.0016(8) 0.0020(8) C20 0.0622(15) 0.0383(11) 0.0279(11) 0.0005(8) -0.0097(10) -0.0021(10) C19 0.0749(16) 0.0316(10) 0.0244(10) -0.0008(8) 0.0073(10) -0.0022(10) C21 0.0426(12) 0.0353(10) 0.0300(10) -0.0006(8) -0.0042(8) -0.0009(9) C11 0.0387(12) 0.0446(12) 0.0324(10) 0.0006(8) -0.0025(9) -0.0098(9) C18 0.0551(13) 0.0318(10) 0.0340(11) -0.0024(8) 0.0153(10) -0.0018(9) C25 0.0412(12) 0.0342(10) 0.0302(10) -0.0021(8) 0.0058(8) -0.0046(9) C33 0.0659(16) 0.0323(11) 0.0335(11) -0.0013(8) 0.0017(10) 0.0031(10) C17 0.0368(11) 0.0342(10) 0.0298(10) -0.0018(8) 0.0029(8) -0.0022(8) C34 0.0543(14) 0.0461(12) 0.0351(12) -0.0028(9) 0.0021(9) 0.0187(10) C32 0.0532(14) 0.0418(12) 0.0397(12) -0.0030(9) 0.0015(10) -0.0097(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 N1 C1 1.148(2) . ? C3 C2 1.370(2) . ? C3 C4 1.414(2) . ? C4 C5 1.416(2) . ? C4 C29 1.430(2) . ? C5 C6 1.418(2) . ? C5 C8 1.423(2) . ? C22 C29 1.377(2) . ? C22 C15 1.420(2) . ? C22 C23 1.496(2) . ? C2 C7 1.407(3) . ? C2 C1 1.441(2) . ? C8 C15 1.378(2) . ? C8 C9 1.500(2) . ? C15 C16 1.490(2) . ? C29 C30 1.488(3) . ? C30 C31 1.384(3) . ? C30 C35 1.387(3) . ? C16 C21 1.388(3) . ? C16 C17 1.392(3) . ? C9 C10 1.387(3) . ? C9 C14 1.387(3) . ? C6 C7 1.361(2) . ? C26 C27 1.380(3) . ? C26 C25 1.383(3) . ? C23 C28 1.385(2) . ? C23 C24 1.391(2) . ? C24 C25 1.382(2) . ? C31 C32 1.378(3) . ? C27 C28 1.386(3) . ? C13 C14 1.377(3) . ? C13 C12 1.378(3) . ? C10 C11 1.378(3) . ? C35 C34 1.388(3) . ? C12 C11 1.381(3) . ? C20 C19 1.379(3) . ? C20 C21 1.384(3) . ? C19 C18 1.375(3) . ? C18 C17 1.385(3) . ? C33 C34 1.371(3) . ? C33 C32 1.377(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 C3 C4 120.93(17) . . ? C3 C4 C5 118.75(16) . . ? C3 C4 C29 121.48(16) . . ? C5 C4 C29 119.77(15) . . ? C4 C5 C6 118.58(15) . . ? C4 C5 C8 119.45(15) . . ? C6 C5 C8 121.95(16) . . ? C29 C22 C15 120.64(16) . . ? C29 C22 C23 121.21(16) . . ? C15 C22 C23 118.11(15) . . ? C3 C2 C7 120.43(16) . . ? C3 C2 C1 119.99(17) . . ? C7 C2 C1 119.58(16) . . ? C15 C8 C5 119.72(16) . . ? C15 C8 C9 120.57(15) . . ? C5 C8 C9 119.66(15) . . ? C8 C15 C22 120.68(15) . . ? C8 C15 C16 120.13(15) . . ? C22 C15 C16 119.18(15) . . ? C22 C29 C4 119.41(16) . . ? C22 C29 C30 121.19(16) . . ? C4 C29 C30 119.36(15) . . ? C31 C30 C35 118.64(17) . . ? C31 C30 C29 120.55(16) . . ? C35 C30 C29 120.81(16) . . ? C21 C16 C17 118.87(17) . . ? C21 C16 C15 122.12(17) . . ? C17 C16 C15 119.01(15) . . ? C10 C9 C14 118.68(17) . . ? C10 C9 C8 119.06(15) . . ? C14 C9 C8 122.25(16) . . ? C7 C6 C5 121.57(17) . . ? N1 C1 C2 179.18(19) . . ? C27 C26 C25 120.02(18) . . ? C6 C7 C2 119.69(16) . . ? C28 C23 C24 119.06(16) . . ? C28 C23 C22 119.72(15) . . ? C24 C23 C22 121.13(15) . . ? C25 C24 C23 120.31(17) . . ? C32 C31 C30 121.09(19) . . ? C26 C27 C28 119.81(18) . . ? C14 C13 C12 120.05(19) . . ? C11 C10 C9 121.02(18) . . ? C30 C35 C34 119.91(19) . . ? C13 C12 C11 120.20(18) . . ? C13 C14 C9 120.54(18) . . ? C23 C28 C27 120.63(17) . . ? C19 C20 C21 120.19(19) . . ? C18 C19 C20 120.32(18) . . ? C20 C21 C16 120.25(19) . . ? C10 C11 C12 119.51(18) . . ? C19 C18 C17 119.69(19) . . ? C24 C25 C26 120.16(18) . . ? C34 C33 C32 119.54(18) . . ? C18 C17 C16 120.68(18) . . ? C33 C34 C35 120.80(19) . . ? C33 C32 C31 120.0(2) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 24.58 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.184 _refine_diff_density_min -0.184 _refine_diff_density_rms 0.044 _database_code_depnum_ccdc_archive 'CCDC 928656' ####################################################################### # # 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_bbb #TrackingRef 'web_deposit_cif_file_1_ansumanbej_1362978648.3h.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C35 H24 O' _chemical_formula_weight 460.54 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'P2(1)2(1)2(1) ' 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' _cell_length_a 8.242(4) _cell_length_b 15.900(8) _cell_length_c 18.948(10) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2483(2) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 1445 _cell_measurement_theta_min 2.50 _cell_measurement_theta_max 15.71 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.07 _exptl_crystal_size_mid 0.04 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.232 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 968 _exptl_absorpt_coefficient_mu 0.072 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9949 _exptl_absorpt_correction_T_max 0.9986 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 10017 _diffrn_reflns_av_R_equivalents 0.0686 _diffrn_reflns_av_sigmaI/netI 0.0391 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.67 _diffrn_reflns_theta_max 17.21 _reflns_number_total 1488 _reflns_number_gt 1302 _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, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'mercury 2.3' _computing_publication_material 'ortep 3v.2' _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^)+(0.1000P)^2^+0.2593P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 3(9) _refine_ls_number_reflns 1488 _refine_ls_number_parameters 327 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0538 _refine_ls_R_factor_gt 0.0468 _refine_ls_wR_factor_ref 0.1213 _refine_ls_wR_factor_gt 0.1137 _refine_ls_goodness_of_fit_ref 0.504 _refine_ls_restrained_S_all 0.504 _refine_ls_shift/su_max 0.196 _refine_ls_shift/su_mean 0.010 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 C2 C 0.2327(11) 0.5042(9) 0.5274(5) 0.116(3) Uani 1 1 d . . . C15 C 0.6701(11) 0.5563(8) 0.3477(5) 0.100(3) Uani 1 1 d . . . C9 C 0.7453(11) 0.4145(6) 0.3952(7) 0.108(3) Uani 1 1 d . . . C16 C 0.8167(13) 0.5550(4) 0.3001(5) 0.098(3) Uani 1 1 d . . . C19 C 1.0979(14) 0.5593(5) 0.2173(7) 0.129(4) Uani 1 1 d . . . H19 H 1.1912 0.5630 0.1899 0.154 Uiso 1 1 calc R . . C29 C 0.4527(13) 0.6395(6) 0.4000(6) 0.099(3) Uani 1 1 d . . . C35 C 0.3892(10) 0.7659(7) 0.4718(5) 0.114(3) Uani 1 1 d . . . H35 H 0.4595 0.7449 0.5059 0.136 Uiso 1 1 calc R . . C4 C 0.4111(13) 0.5684(8) 0.4415(5) 0.103(3) Uani 1 1 d . . . C13 C 0.9308(14) 0.3277(9) 0.4578(6) 0.145(4) Uani 1 1 d . . . H13 H 0.9840 0.3143 0.4996 0.174 Uiso 1 1 calc R . . C14 C 0.8267(14) 0.3945(7) 0.4558(5) 0.125(3) Uani 1 1 d . . . H14 H 0.8111 0.4268 0.4962 0.149 Uiso 1 1 calc R . . C8 C 0.6365(14) 0.4896(6) 0.3911(5) 0.103(3) Uani 1 1 d . . . C22 C 0.5769(14) 0.6325(7) 0.3512(5) 0.101(3) Uani 1 1 d . . . C20 C 0.9485(19) 0.5532(5) 0.1871(5) 0.127(4) Uani 1 1 d . . . H20 H 0.9411 0.5501 0.1382 0.152 Uiso 1 1 calc R . . C6 C 0.4406(15) 0.4222(5) 0.4783(6) 0.113(3) Uani 1 1 d . . . H6 H 0.4947 0.3710 0.4750 0.136 Uiso 1 1 calc R . . C31 C 0.2660(13) 0.7547(7) 0.3590(5) 0.119(3) Uani 1 1 d . . . H31 H 0.2496 0.7257 0.3170 0.143 Uiso 1 1 calc R . . C3 C 0.2804(15) 0.5734(5) 0.4881(6) 0.113(3) Uani 1 1 d . . . H3 H 0.2245 0.6239 0.4928 0.136 Uiso 1 1 calc R . . C17 C 0.9696(17) 0.5579(4) 0.3301(4) 0.113(3) Uani 1 1 d . . . H17 H 0.9803 0.5587 0.3789 0.136 Uiso 1 1 calc R . . C10 C 0.7692(12) 0.3677(8) 0.3356(6) 0.123(3) Uani 1 1 d . . . H10 H 0.7147 0.3809 0.2941 0.148 Uiso 1 1 calc R . . C7 C 0.3142(15) 0.4280(7) 0.5209(5) 0.121(3) Uani 1 1 d . . . H7 H 0.2798 0.3813 0.5464 0.145 Uiso 1 1 calc R . . C11 C 0.8766(17) 0.2998(8) 0.3379(6) 0.139(4) Uani 1 1 d . . . H11 H 0.8927 0.2678 0.2974 0.167 Uiso 1 1 calc R . . C34 C 0.3102(14) 0.8404(8) 0.4836(5) 0.127(3) Uani 1 1 d . . . H34 H 0.3230 0.8682 0.5265 0.153 Uiso 1 1 calc R . . C30 C 0.3663(12) 0.7212(6) 0.4100(6) 0.103(3) Uani 1 1 d . . . C1 C 0.1034(15) 0.5087(7) 0.5759(6) 0.148(4) Uani 1 1 d . . . H1 H 0.0553 0.5611 0.5820 0.178 Uiso 1 1 calc R . . C33 C 0.2123(13) 0.8742(5) 0.4324(8) 0.130(3) Uani 1 1 d . . . H33 H 0.1617 0.9257 0.4397 0.156 Uiso 1 1 calc R . . C12 C 0.9576(13) 0.2795(6) 0.3975(9) 0.145(4) Uani 1 1 d . . . H12 H 1.0295 0.2344 0.3983 0.174 Uiso 1 1 calc R . . C32 C 0.1894(10) 0.8309(8) 0.3699(6) 0.124(3) Uani 1 1 d . . . H32 H 0.1225 0.8532 0.3351 0.149 Uiso 1 1 calc R . . C23 C 0.6222(11) 0.7050(7) 0.3052(6) 0.104(3) Uani 1 1 d . . . C18 C 1.1059(13) 0.5597(5) 0.2884(7) 0.125(3) Uani 1 1 d . . . H18 H 1.2072 0.5613 0.3099 0.149 Uiso 1 1 calc R . . C21 C 0.8069(12) 0.5515(4) 0.2267(6) 0.116(3) Uani 1 1 d . . . H21 H 0.7065 0.5481 0.2044 0.140 Uiso 1 1 calc R . . C5 C 0.4976(14) 0.4916(8) 0.4370(5) 0.108(3) Uani 1 1 d . . . O1 O 0.0452(9) 0.4477(5) 0.6126(4) 0.182(4) Uani 1 1 d . . . C25 C 0.6055(14) 0.7767(9) 0.1942(5) 0.140(4) Uani 1 1 d . . . H25 H 0.5676 0.7786 0.1480 0.168 Uiso 1 1 calc R . . C27 C 0.7527(12) 0.8360(7) 0.2883(9) 0.146(4) Uani 1 1 d . . . H27 H 0.8131 0.8803 0.3065 0.175 Uiso 1 1 calc R . . C26 C 0.7000(15) 0.8401(8) 0.2194(8) 0.150(4) Uani 1 1 d . . . H26 H 0.7283 0.8853 0.1908 0.180 Uiso 1 1 calc R . . C24 C 0.5664(10) 0.7103(6) 0.2366(7) 0.121(3) Uani 1 1 d . . . H24 H 0.5006 0.6677 0.2189 0.145 Uiso 1 1 calc R . . C28 C 0.7187(12) 0.7685(8) 0.3307(5) 0.130(3) Uani 1 1 d . . . H28 H 0.7604 0.7657 0.3763 0.156 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C2 0.072(6) 0.165(10) 0.110(7) -0.023(8) 0.023(5) 0.005(8) C15 0.099(8) 0.093(8) 0.109(6) 0.005(6) 0.003(6) -0.009(7) C9 0.115(7) 0.093(7) 0.116(7) -0.010(7) 0.009(7) 0.005(6) C16 0.091(8) 0.082(5) 0.120(9) -0.007(5) -0.010(7) -0.007(4) C19 0.099(9) 0.114(6) 0.173(13) -0.011(6) 0.019(7) -0.016(5) C29 0.098(7) 0.100(9) 0.098(7) -0.001(7) -0.002(6) 0.001(7) C35 0.114(6) 0.101(7) 0.125(9) -0.005(6) -0.003(5) 0.007(6) C4 0.097(7) 0.123(11) 0.090(6) 0.006(7) 0.021(6) -0.028(9) C13 0.140(8) 0.130(8) 0.164(11) 0.028(8) -0.019(7) 0.007(7) C14 0.144(8) 0.110(7) 0.120(9) 0.000(5) -0.023(7) 0.012(7) C8 0.106(8) 0.103(9) 0.100(6) -0.009(7) -0.008(7) -0.004(8) C22 0.103(7) 0.100(9) 0.101(7) 0.003(7) -0.006(6) -0.001(7) C20 0.152(9) 0.105(6) 0.124(7) -0.008(5) 0.051(10) -0.010(6) C6 0.137(9) 0.081(7) 0.122(6) 0.014(6) -0.010(7) -0.002(6) C31 0.125(6) 0.104(8) 0.128(8) -0.002(6) 0.000(7) 0.014(6) C3 0.123(9) 0.102(7) 0.115(7) 0.013(6) -0.015(7) -0.021(7) C17 0.123(8) 0.109(6) 0.107(6) -0.007(4) 0.017(8) 0.003(5) C10 0.118(7) 0.108(7) 0.144(10) 0.009(8) 0.007(6) 0.012(6) C7 0.094(6) 0.150(10) 0.118(7) -0.021(6) 0.018(6) 0.002(7) C11 0.167(10) 0.122(9) 0.129(9) -0.006(6) -0.003(8) -0.005(8) C34 0.136(7) 0.130(9) 0.116(8) -0.003(7) 0.002(7) -0.010(7) C30 0.104(6) 0.098(7) 0.106(7) -0.005(7) 0.002(6) -0.002(6) C1 0.144(10) 0.146(9) 0.155(9) 0.002(7) -0.015(8) 0.016(7) C33 0.143(9) 0.106(7) 0.141(8) -0.012(8) 0.029(8) 0.000(6) C12 0.146(8) 0.111(7) 0.177(9) 0.001(9) 0.019(9) 0.017(6) C32 0.122(7) 0.119(8) 0.132(9) 0.013(6) 0.000(6) 0.015(7) C23 0.106(6) 0.107(8) 0.099(8) 0.002(7) 0.007(5) 0.008(6) C18 0.127(9) 0.119(6) 0.128(8) -0.005(6) 0.003(8) 0.003(5) C21 0.134(10) 0.110(6) 0.105(8) -0.007(5) -0.018(7) -0.005(5) C5 0.111(8) 0.095(9) 0.117(7) -0.017(8) -0.008(7) 0.012(9) O1 0.155(6) 0.218(7) 0.174(6) 0.049(5) 0.006(4) -0.013(5) C25 0.153(9) 0.149(8) 0.119(7) 0.033(9) 0.015(7) 0.010(7) C27 0.135(8) 0.117(9) 0.185(11) 0.011(8) -0.005(8) -0.001(7) C26 0.139(9) 0.130(9) 0.181(13) 0.035(8) 0.020(8) 0.008(8) C24 0.125(7) 0.129(8) 0.108(8) 0.000(6) -0.002(6) 0.009(6) C28 0.147(8) 0.099(6) 0.144(8) 0.014(8) -0.017(7) -0.016(6) _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 1.385(11) . ? C2 C7 1.392(11) . ? C2 C1 1.409(12) . ? C15 C8 1.370(9) . ? C15 C22 1.437(10) . ? C15 C16 1.507(10) . ? C9 C10 1.366(10) . ? C9 C14 1.368(10) . ? C9 C8 1.495(11) . ? C16 C17 1.383(10) . ? C16 C21 1.395(9) . ? C19 C18 1.348(10) . ? C19 C20 1.361(11) . ? C19 H19 0.9300 . ? C29 C22 1.384(9) . ? C29 C4 1.420(10) . ? C29 C30 1.494(11) . ? C35 C34 1.371(10) . ? C35 C30 1.382(10) . ? C35 H35 0.9300 . ? C4 C3 1.395(11) . ? C4 C5 1.415(10) . ? C13 C14 1.366(11) . ? C13 C12 1.393(11) . ? C13 H13 0.9300 . ? C14 H14 0.9300 . ? C8 C5 1.439(10) . ? C22 C23 1.492(10) . ? C20 C21 1.387(11) . ? C20 H20 0.9300 . ? C6 C7 1.321(10) . ? C6 C5 1.432(11) . ? C6 H6 0.9300 . ? C31 C30 1.378(10) . ? C31 C32 1.382(10) . ? C31 H31 0.9300 . ? C3 H3 0.9300 . ? C17 C18 1.374(10) . ? C17 H17 0.9300 . ? C10 C11 1.397(11) . ? C10 H10 0.9300 . ? C7 H7 0.9300 . ? C11 C12 1.352(11) . ? C11 H11 0.9300 . ? C34 C33 1.371(10) . ? C34 H34 0.9300 . ? C1 O1 1.286(11) . ? C1 H1 0.9300 . ? C33 C32 1.383(10) . ? C33 H33 0.9300 . ? C12 H12 0.9300 . ? C32 H32 0.9300 . ? C23 C28 1.374(10) . ? C23 C24 1.381(10) . ? C18 H18 0.9300 . ? C21 H21 0.9300 . ? C25 C26 1.361(12) . ? C25 C24 1.364(11) . ? C25 H25 0.9300 . ? C27 C28 1.371(11) . ? C27 C26 1.376(11) . ? C27 H27 0.9300 . ? C26 H26 0.9300 . ? C24 H24 0.9300 . ? C28 H28 0.9300 . ? 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 C7 120.5(8) . . ? C3 C2 C1 121.7(13) . . ? C7 C2 C1 117.8(12) . . ? C8 C15 C22 121.2(8) . . ? C8 C15 C16 120.7(10) . . ? C22 C15 C16 117.9(10) . . ? C10 C9 C14 119.8(9) . . ? C10 C9 C8 118.6(11) . . ? C14 C9 C8 121.6(11) . . ? C17 C16 C21 117.6(8) . . ? C17 C16 C15 119.0(9) . . ? C21 C16 C15 123.4(10) . . ? C18 C19 C20 117.7(9) . . ? C18 C19 H19 121.2 . . ? C20 C19 H19 121.2 . . ? C22 C29 C4 119.0(9) . . ? C22 C29 C30 120.5(10) . . ? C4 C29 C30 120.5(11) . . ? C34 C35 C30 121.2(8) . . ? C34 C35 H35 119.4 . . ? C30 C35 H35 119.4 . . ? C3 C4 C5 118.5(10) . . ? C3 C4 C29 119.4(13) . . ? C5 C4 C29 122.1(10) . . ? C14 C13 C12 120.3(9) . . ? C14 C13 H13 119.8 . . ? C12 C13 H13 119.8 . . ? C13 C14 C9 120.8(8) . . ? C13 C14 H14 119.6 . . ? C9 C14 H14 119.6 . . ? C15 C8 C5 120.4(9) . . ? C15 C8 C9 121.9(11) . . ? C5 C8 C9 117.6(11) . . ? C29 C22 C15 119.6(8) . . ? C29 C22 C23 120.9(10) . . ? C15 C22 C23 119.4(11) . . ? C19 C20 C21 122.4(8) . . ? C19 C20 H20 118.8 . . ? C21 C20 H20 118.8 . . ? C7 C6 C5 122.6(8) . . ? C7 C6 H6 118.7 . . ? C5 C6 H6 118.7 . . ? C30 C31 C32 120.5(8) . . ? C30 C31 H31 119.7 . . ? C32 C31 H31 119.7 . . ? C2 C3 C4 120.9(9) . . ? C2 C3 H3 119.6 . . ? C4 C3 H3 119.6 . . ? C18 C17 C16 120.6(7) . . ? C18 C17 H17 119.7 . . ? C16 C17 H17 119.7 . . ? C9 C10 C11 119.2(9) . . ? C9 C10 H10 120.4 . . ? C11 C10 H10 120.4 . . ? C6 C7 C2 119.7(9) . . ? C6 C7 H7 120.1 . . ? C2 C7 H7 120.2 . . ? C12 C11 C10 121.5(9) . . ? C12 C11 H11 119.2 . . ? C10 C11 H11 119.2 . . ? C33 C34 C35 120.1(8) . . ? C33 C34 H34 119.9 . . ? C35 C34 H34 119.9 . . ? C31 C30 C35 118.5(8) . . ? C31 C30 C29 122.2(9) . . ? C35 C30 C29 119.3(11) . . ? O1 C1 C2 126.6(10) . . ? O1 C1 H1 116.7 . . ? C2 C1 H1 116.7 . . ? C34 C33 C32 119.5(8) . . ? C34 C33 H33 120.3 . . ? C32 C33 H33 120.3 . . ? C11 C12 C13 118.4(9) . . ? C11 C12 H12 120.8 . . ? C13 C12 H12 120.8 . . ? C31 C32 C33 120.1(8) . . ? C31 C32 H32 120.0 . . ? C33 C32 H32 120.0 . . ? C28 C23 C24 118.7(8) . . ? C28 C23 C22 120.4(10) . . ? C24 C23 C22 120.9(10) . . ? C19 C18 C17 122.3(9) . . ? C19 C18 H18 118.8 . . ? C17 C18 H18 118.8 . . ? C20 C21 C16 119.3(8) . . ? C20 C21 H21 120.3 . . ? C16 C21 H21 120.3 . . ? C4 C5 C6 117.8(10) . . ? C4 C5 C8 117.2(10) . . ? C6 C5 C8 125.0(12) . . ? C26 C25 C24 120.1(9) . . ? C26 C25 H25 119.9 . . ? C24 C25 H25 119.9 . . ? C28 C27 C26 122.0(10) . . ? C28 C27 H27 119.0 . . ? C26 C27 H27 119.0 . . ? C25 C26 C27 118.5(10) . . ? C25 C26 H26 120.7 . . ? C27 C26 H26 120.7 . . ? C25 C24 C23 121.5(9) . . ? C25 C24 H24 119.3 . . ? C23 C24 H24 119.3 . . ? C27 C28 C23 119.1(9) . . ? C27 C28 H28 120.4 . . ? C23 C28 H28 120.4 . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 17.21 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.038 _refine_diff_density_min -0.016 _refine_diff_density_rms 0.004 _database_code_depnum_ccdc_archive 'CCDC 928657'