# Electronic Supplementary Material (ESI) for Chemical Communications # 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_global data_12rh002 #TrackingRef 'Cis-DATPE.cif' _audit_creation_date 2012-08-14T11:36:55-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_sum 'C34 H28 O2' _chemical_formula_weight 468.56 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/c 1' 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 11.69544(18) _cell_length_b 5.52783(10) _cell_length_c 42.0817(7) _cell_angle_alpha 90 _cell_angle_beta 103.3059(16) _cell_angle_gamma 90 _cell_volume 2647.56(8) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 10245 _cell_measurement_theta_min 1.4887 _cell_measurement_theta_max 28.0969 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description rod _exptl_crystal_colour colorless _exptl_crystal_size_max 0.3659 _exptl_crystal_size_mid 0.177 _exptl_crystal_size_min 0.0549 _exptl_crystal_density_diffrn 1.176 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 992 loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist -16 0 26 0.0493 16 0 -26 0.0493 -13 0 -23 0.0275 13 0 23 0.0275 0 -8 -4 0.1767 0 8 4 0.1767 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.072 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.35.10 (release 06-04-2011 CrysAlis171 .NET) (compiled Apr 6 2011,09:17:13) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_absorpt_correction_T_min 0.67007 _exptl_absorpt_correction_T_max 1 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_detector_area_resol_mean 16.0965 _diffrn_orient_matrix_ub_11 -0.054173 _diffrn_orient_matrix_ub_12 -0.0438318 _diffrn_orient_matrix_ub_13 -0.009493 _diffrn_orient_matrix_ub_21 0.0269817 _diffrn_orient_matrix_ub_22 -0.0224739 _diffrn_orient_matrix_ub_23 -0.0131798 _diffrn_orient_matrix_ub_31 0.0149194 _diffrn_orient_matrix_ub_32 -0.1184604 _diffrn_orient_matrix_ub_33 0.0060114 _diffrn_measurement_device_type 'SuperNova, Single source at offset), Eos' _diffrn_measurement_method '\w scans' _diffrn_reflns_av_R_equivalents 0.0315 _diffrn_reflns_av_unetI/netI 0.0258 _diffrn_reflns_number 29347 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -54 _diffrn_reflns_limit_l_max 54 _diffrn_reflns_theta_min 1.79 _diffrn_reflns_theta_max 28.16 _diffrn_reflns_theta_full 25 _diffrn_measured_fraction_theta_full 1 _diffrn_measured_fraction_theta_max 0.932 _reflns_number_total 6049 _reflns_number_gt 4862 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.35.10 (release 06-04-2011 CrysAlis171 .NET) (compiled Apr 6 2011,09:17:13) ; _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.35.10 (release 06-04-2011 CrysAlis171 .NET) (compiled Apr 6 2011,09:17:13) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.35.10 (release 06-04-2011 CrysAlis171 .NET) (compiled Apr 6 2011,09:17:13) ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0275P)^2^+0.9309P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 6049 _refine_ls_number_parameters 327 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0607 _refine_ls_R_factor_gt 0.0455 _refine_ls_wR_factor_ref 0.0977 _refine_ls_wR_factor_gt 0.0904 _refine_ls_goodness_of_fit_ref 1.055 _refine_ls_restrained_S_all 1.055 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.211 _refine_diff_density_min -0.172 _refine_diff_density_rms 0.033 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.64509(9) 0.6043(2) 0.52932(2) 0.0519(3) Uani 1 1 d . . . H1 H 0.6308 0.6213 0.5089 0.078 Uiso 1 1 calc R . . C2 C 0.78674(11) 0.1819(2) 0.34192(3) 0.0276(3) Uani 1 1 d . . . C3 C 0.86106(10) 0.1890(2) 0.29060(3) 0.0252(3) Uani 1 1 d . . . C4 C 0.87451(11) 0.2222(2) 0.32650(3) 0.0261(3) Uani 1 1 d . . . O2 O 1.54792(9) 0.6582(2) 0.46382(3) 0.0476(3) Uani 1 1 d . . . H2 H 1.4848 0.583 0.4628 0.071 Uiso 1 1 calc R . . C6 C 0.66498(11) 0.1176(2) 0.32383(3) 0.0282(3) Uani 1 1 d . . . C7 C 0.99080(11) 0.3250(2) 0.34352(3) 0.0265(3) Uani 1 1 d . . . C8 C 0.80962(11) -0.0149(3) 0.27363(3) 0.0316(3) Uani 1 1 d . . . H8 H 0.7825 -0.143 0.285 0.038 Uiso 1 1 calc R . . C9 C 0.80134(11) 0.2059(2) 0.37796(3) 0.0288(3) Uani 1 1 d . . . C10 C 0.71787(12) 0.3342(3) 0.39012(3) 0.0337(3) Uani 1 1 d . . . H10 H 0.6521 0.4027 0.3753 0.04 Uiso 1 1 calc R . . C11 C 0.90204(10) 0.3707(2) 0.27310(3) 0.0266(3) Uani 1 1 d . . . H11 H 0.9389 0.5093 0.2843 0.032 Uiso 1 1 calc R . . C12 C 0.99714(11) 0.5440(3) 0.36020(3) 0.0316(3) Uani 1 1 d . . . H12 H 0.9268 0.6228 0.362 0.038 Uiso 1 1 calc R . . C13 C 1.10438(11) 0.6481(3) 0.37409(3) 0.0329(3) Uani 1 1 d . . . H13 H 1.1067 0.798 0.3853 0.039 Uiso 1 1 calc R . . C14 C 0.60416(11) 0.2588(3) 0.29814(3) 0.0337(3) Uani 1 1 d . . . H14 H 0.6402 0.3993 0.2919 0.04 Uiso 1 1 calc R . . C15 C 0.72900(12) 0.3635(3) 0.42330(3) 0.0375(3) Uani 1 1 d . . . H15 H 0.6722 0.4554 0.431 0.045 Uiso 1 1 calc R . . C16 C 0.79789(11) -0.0313(3) 0.24007(3) 0.0357(3) Uani 1 1 d . . . H16 H 0.7625 -0.1707 0.2287 0.043 Uiso 1 1 calc R . . C17 C 0.88997(11) 0.3529(3) 0.23958(3) 0.0313(3) Uani 1 1 d . . . H17 H 0.9182 0.4789 0.2281 0.038 Uiso 1 1 calc R . . C18 C 0.82295(12) 0.2592(3) 0.44559(3) 0.0367(3) Uani 1 1 d . . . C19 C 0.83703(11) 0.1527(3) 0.22303(3) 0.0341(3) Uani 1 1 d . . . H19 H 0.8275 0.1411 0.2 0.041 Uiso 1 1 calc R . . C20 C 1.20403(11) 0.3162(3) 0.35556(3) 0.0319(3) Uani 1 1 d . . . H20 H 1.2744 0.2353 0.3542 0.038 Uiso 1 1 calc R . . C21 C 0.89397(12) 0.1005(3) 0.40043(3) 0.0377(3) Uani 1 1 d . . . H21 H 0.9512 0.0101 0.3927 0.045 Uiso 1 1 calc R . . C22 C 1.09605(11) 0.2148(2) 0.34122(3) 0.0285(3) Uani 1 1 d . . . H22 H 1.0936 0.0671 0.3296 0.034 Uiso 1 1 calc R . . C23 C 1.20952(11) 0.5365(3) 0.37197(3) 0.0309(3) Uani 1 1 d . . . C24 C 0.60904(12) -0.0841(3) 0.33301(4) 0.0384(3) Uani 1 1 d . . . H24 H 0.6485 -0.18 0.3509 0.046 Uiso 1 1 calc R . . C25 C 0.83657(13) 0.3381(3) 0.50797(4) 0.0457(4) Uani 1 1 d . . . C26 C 0.83248(13) 0.2950(3) 0.48003(4) 0.0432(4) Uani 1 1 d . . . C27 C 1.40207(13) 0.7730(3) 0.39922(4) 0.0428(4) Uani 1 1 d . . . C28 C 0.43811(13) -0.0069(3) 0.29054(4) 0.0460(4) Uani 1 1 d . . . H28 H 0.3613 -0.0507 0.2789 0.055 Uiso 1 1 calc R . . C29 C 0.83742(14) 0.4102(3) 0.54162(3) 0.0484(4) Uani 1 1 d . . . H29A H 0.9195 0.4372 0.5538 0.058 Uiso 1 1 calc R . . H29B H 0.8043 0.2776 0.5525 0.058 Uiso 1 1 calc R . . C30 C 0.90458(13) 0.1244(3) 0.43365(3) 0.0417(4) Uani 1 1 d . . . H30 H 0.968 0.0483 0.4485 0.05 Uiso 1 1 calc R . . C31 C 1.31845(12) 0.6559(3) 0.38664(3) 0.0370(3) Uani 1 1 d . . . C32 C 0.49652(13) -0.1467(3) 0.31636(4) 0.0453(4) Uani 1 1 d . . . H32 H 0.4596 -0.2858 0.3227 0.054 Uiso 1 1 calc R . . C33 C 1.52268(15) 0.8997(3) 0.45299(4) 0.0521(4) Uani 1 1 d . . . H33A H 1.5889 1.0058 0.4634 0.062 Uiso 1 1 calc R . . H33B H 1.4516 0.9564 0.4598 0.062 Uiso 1 1 calc R . . C34 C 0.49148(12) 0.1967(3) 0.28161(4) 0.0424(4) Uani 1 1 d . . . H34 H 0.4508 0.2946 0.2641 0.051 Uiso 1 1 calc R . . C35 C 1.50277(14) 0.9192(3) 0.41617(4) 0.0537(5) Uani 1 1 d . . . H35A H 1.4889 1.0907 0.4096 0.064 Uiso 1 1 calc R . . H35B H 1.5743 0.8647 0.4094 0.064 Uiso 1 1 calc R . . C36 C 0.76673(13) 0.6387(3) 0.54260(4) 0.0461(4) Uani 1 1 d . . . H36A H 0.7785 0.6935 0.5655 0.055 Uiso 1 1 calc R . . H36B H 0.7961 0.7675 0.5302 0.055 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 O1 0.0459(6) 0.0777(9) 0.0326(5) 0.0022(6) 0.0102(5) 0.0007(6) C2 0.0303(6) 0.0264(7) 0.0277(6) -0.0002(5) 0.0101(5) 0.0008(5) C3 0.0211(6) 0.0284(7) 0.0274(6) -0.0022(5) 0.0082(5) 0.0009(5) C4 0.0280(6) 0.0247(7) 0.0265(6) -0.0010(5) 0.0080(5) 0.0001(5) O2 0.0367(5) 0.0684(8) 0.0368(6) 0.0042(6) 0.0063(5) 0.0007(6) C6 0.0282(6) 0.0294(7) 0.0304(7) -0.0037(5) 0.0135(5) -0.0013(5) C7 0.0289(6) 0.0304(7) 0.0209(6) 0.0017(5) 0.0076(5) -0.0011(5) C8 0.0282(6) 0.0296(7) 0.0400(8) -0.0055(6) 0.0140(5) -0.0033(6) C9 0.0313(6) 0.0300(7) 0.0276(6) -0.0004(5) 0.0121(5) -0.0028(6) C10 0.0338(7) 0.0383(8) 0.0312(7) 0.0024(6) 0.0117(5) 0.0035(6) C11 0.0228(6) 0.0292(7) 0.0278(6) -0.0022(5) 0.0061(5) -0.0005(5) C12 0.0298(6) 0.0336(8) 0.0320(7) -0.0027(6) 0.0084(5) 0.0013(6) C13 0.0365(7) 0.0321(8) 0.0293(7) -0.0024(6) 0.0060(5) -0.0025(6) C14 0.0294(7) 0.0329(8) 0.0412(8) 0.0016(6) 0.0133(6) -0.0006(6) C15 0.0395(7) 0.0416(9) 0.0360(7) -0.0028(6) 0.0179(6) 0.0036(7) C16 0.0273(7) 0.0402(8) 0.0388(8) -0.0168(6) 0.0061(6) -0.0007(6) C17 0.0267(6) 0.0396(8) 0.0282(7) 0.0029(6) 0.0078(5) 0.0031(6) C18 0.0402(7) 0.0431(9) 0.0289(7) -0.0033(6) 0.0124(6) -0.0029(7) C19 0.0264(6) 0.0488(9) 0.0267(6) -0.0058(6) 0.0052(5) 0.0066(6) C20 0.0287(6) 0.0407(8) 0.0262(6) 0.0051(6) 0.0062(5) 0.0053(6) C21 0.0372(7) 0.0449(9) 0.0335(7) -0.0015(6) 0.0133(6) 0.0098(7) C22 0.0336(7) 0.0302(7) 0.0224(6) 0.0006(5) 0.0079(5) 0.0027(6) C23 0.0312(6) 0.0393(8) 0.0205(6) 0.0060(6) 0.0023(5) -0.0039(6) C24 0.0394(8) 0.0364(8) 0.0418(8) 0.0039(6) 0.0141(6) -0.0048(6) C25 0.0444(8) 0.0592(11) 0.0331(8) -0.0037(7) 0.0081(6) 0.0047(8) C26 0.0420(8) 0.0548(10) 0.0338(8) -0.0039(7) 0.0108(6) 0.0011(7) C27 0.0367(8) 0.0531(10) 0.0348(8) 0.0088(7) 0.0005(6) -0.0069(7) C28 0.0283(7) 0.0515(10) 0.0581(10) -0.0076(8) 0.0098(7) -0.0080(7) C29 0.0511(9) 0.0668(12) 0.0259(7) -0.0046(7) 0.0056(6) 0.0035(8) C30 0.0400(8) 0.0539(10) 0.0308(7) 0.0021(7) 0.0073(6) 0.0095(7) C31 0.0345(7) 0.0461(9) 0.0283(7) 0.0070(6) 0.0027(6) -0.0027(7) C32 0.0408(8) 0.0390(9) 0.0599(10) -0.0023(8) 0.0196(7) -0.0134(7) C33 0.0429(9) 0.0571(11) 0.0506(10) -0.0121(8) -0.0008(7) -0.0064(8) C34 0.0303(7) 0.0489(10) 0.0469(9) 0.0039(7) 0.0064(6) 0.0020(7) C35 0.0422(9) 0.0581(11) 0.0532(10) 0.0103(9) -0.0049(7) -0.0170(8) C36 0.0492(9) 0.0602(11) 0.0282(7) -0.0067(7) 0.0074(6) -0.0045(8) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C36 1.4165(18) . ? O1 H1 0.84 . ? C2 C4 1.3530(17) . ? C2 C9 1.4925(17) . ? C2 C6 1.4950(17) . ? C3 C11 1.3938(18) . ? C3 C8 1.3947(18) . ? C3 C4 1.4938(16) . ? C4 C7 1.4957(17) . ? O2 C33 1.420(2) . ? O2 H2 0.84 . ? C6 C14 1.3892(19) . ? C6 C24 1.3915(19) . ? C7 C12 1.3928(18) . ? C7 C22 1.3963(17) . ? C8 C16 1.3899(18) . ? C8 H8 0.95 . ? C9 C21 1.3914(19) . ? C9 C10 1.3956(18) . ? C10 C15 1.3817(19) . ? C10 H10 0.95 . ? C11 C17 1.3883(17) . ? C11 H11 0.95 . ? C12 C13 1.3817(18) . ? C12 H12 0.95 . ? C13 C23 1.3971(19) . ? C13 H13 0.95 . ? C14 C34 1.3844(19) . ? C14 H14 0.95 . ? C15 C18 1.395(2) . ? C15 H15 0.95 . ? C16 C19 1.382(2) . ? C16 H16 0.95 . ? C17 C19 1.376(2) . ? C17 H17 0.95 . ? C18 C30 1.393(2) . ? C18 C26 1.4414(19) . ? C19 H19 0.95 . ? C20 C22 1.3864(18) . ? C20 C23 1.394(2) . ? C20 H20 0.95 . ? C21 C30 1.3814(19) . ? C21 H21 0.95 . ? C22 H22 0.95 . ? C23 C31 1.4416(19) . ? C24 C32 1.385(2) . ? C24 H24 0.95 . ? C25 C26 1.190(2) . ? C25 C29 1.469(2) . ? C27 C31 1.191(2) . ? C27 C35 1.471(2) . ? C28 C32 1.379(2) . ? C28 C34 1.381(2) . ? C28 H28 0.95 . ? C29 C36 1.515(2) . ? C29 H29A 0.99 . ? C29 H29B 0.99 . ? C30 H30 0.95 . ? C32 H32 0.95 . ? C33 C35 1.517(2) . ? C33 H33A 0.99 . ? C33 H33B 0.99 . ? C34 H34 0.95 . ? C35 H35A 0.99 . ? C35 H35B 0.99 . ? C36 H36A 0.99 . ? C36 H36B 0.99 . ? 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 C36 O1 H1 109.5 . . ? C4 C2 C9 123.42(11) . . ? C4 C2 C6 122.27(11) . . ? C9 C2 C6 114.29(10) . . ? C11 C3 C8 118.16(11) . . ? C11 C3 C4 118.50(11) . . ? C8 C3 C4 123.34(11) . . ? C2 C4 C3 123.36(11) . . ? C2 C4 C7 122.65(11) . . ? C3 C4 C7 113.78(10) . . ? C33 O2 H2 109.5 . . ? C14 C6 C24 118.49(12) . . ? C14 C6 C2 121.30(12) . . ? C24 C6 C2 120.20(12) . . ? C12 C7 C22 117.93(12) . . ? C12 C7 C4 120.57(11) . . ? C22 C7 C4 121.34(12) . . ? C16 C8 C3 120.19(13) . . ? C16 C8 H8 119.9 . . ? C3 C8 H8 119.9 . . ? C21 C9 C10 117.67(12) . . ? C21 C9 C2 122.85(12) . . ? C10 C9 C2 119.46(12) . . ? C15 C10 C9 121.28(13) . . ? C15 C10 H10 119.4 . . ? C9 C10 H10 119.4 . . ? C17 C11 C3 121.27(12) . . ? C17 C11 H11 119.4 . . ? C3 C11 H11 119.4 . . ? C13 C12 C7 120.89(12) . . ? C13 C12 H12 119.6 . . ? C7 C12 H12 119.6 . . ? C12 C13 C23 121.02(13) . . ? C12 C13 H13 119.5 . . ? C23 C13 H13 119.5 . . ? C34 C14 C6 120.63(13) . . ? C34 C14 H14 119.7 . . ? C6 C14 H14 119.7 . . ? C10 C15 C18 120.49(13) . . ? C10 C15 H15 119.8 . . ? C18 C15 H15 119.8 . . ? C19 C16 C8 120.82(13) . . ? C19 C16 H16 119.6 . . ? C8 C16 H16 119.6 . . ? C19 C17 C11 119.97(13) . . ? C19 C17 H17 120 . . ? C11 C17 H17 120 . . ? C30 C18 C15 118.55(13) . . ? C30 C18 C26 122.37(13) . . ? C15 C18 C26 119.08(13) . . ? C17 C19 C16 119.57(12) . . ? C17 C19 H19 120.2 . . ? C16 C19 H19 120.2 . . ? C22 C20 C23 120.14(12) . . ? C22 C20 H20 119.9 . . ? C23 C20 H20 119.9 . . ? C30 C21 C9 121.50(13) . . ? C30 C21 H21 119.3 . . ? C9 C21 H21 119.3 . . ? C20 C22 C7 121.53(13) . . ? C20 C22 H22 119.2 . . ? C7 C22 H22 119.2 . . ? C20 C23 C13 118.47(12) . . ? C20 C23 C31 123.20(13) . . ? C13 C23 C31 118.32(13) . . ? C32 C24 C6 120.82(14) . . ? C32 C24 H24 119.6 . . ? C6 C24 H24 119.6 . . ? C26 C25 C29 175.44(19) . . ? C25 C26 C18 175.81(18) . . ? C31 C27 C35 177.15(17) . . ? C32 C28 C34 119.88(14) . . ? C32 C28 H28 120.1 . . ? C34 C28 H28 120.1 . . ? C25 C29 C36 111.69(13) . . ? C25 C29 H29A 109.3 . . ? C36 C29 H29A 109.3 . . ? C25 C29 H29B 109.3 . . ? C36 C29 H29B 109.3 . . ? H29A C29 H29B 107.9 . . ? C21 C30 C18 120.46(13) . . ? C21 C30 H30 119.8 . . ? C18 C30 H30 119.8 . . ? C27 C31 C23 173.72(17) . . ? C28 C32 C24 119.95(14) . . ? C28 C32 H32 120 . . ? C24 C32 H32 120 . . ? O2 C33 C35 111.50(14) . . ? O2 C33 H33A 109.3 . . ? C35 C33 H33A 109.3 . . ? O2 C33 H33B 109.3 . . ? C35 C33 H33B 109.3 . . ? H33A C33 H33B 108 . . ? C28 C34 C14 120.20(15) . . ? C28 C34 H34 119.9 . . ? C14 C34 H34 119.9 . . ? C27 C35 C33 111.96(14) . . ? C27 C35 H35A 109.2 . . ? C33 C35 H35A 109.2 . . ? C27 C35 H35B 109.2 . . ? C33 C35 H35B 109.2 . . ? H35A C35 H35B 107.9 . . ? O1 C36 C29 112.48(14) . . ? O1 C36 H36A 109.1 . . ? C29 C36 H36A 109.1 . . ? O1 C36 H36B 109.1 . . ? C29 C36 H36B 109.1 . . ? H36A C36 H36B 107.8 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C9 C2 C4 C3 177.60(12) . . . . ? C6 C2 C4 C3 -4.6(2) . . . . ? C9 C2 C4 C7 -8.0(2) . . . . ? C6 C2 C4 C7 169.85(12) . . . . ? C11 C3 C4 C2 132.99(13) . . . . ? C8 C3 C4 C2 -47.10(19) . . . . ? C11 C3 C4 C7 -41.90(16) . . . . ? C8 C3 C4 C7 138.00(12) . . . . ? C4 C2 C6 C14 -53.11(19) . . . . ? C9 C2 C6 C14 124.87(13) . . . . ? C4 C2 C6 C24 128.34(14) . . . . ? C9 C2 C6 C24 -53.67(17) . . . . ? C2 C4 C7 C12 -55.08(18) . . . . ? C3 C4 C7 C12 119.85(13) . . . . ? C2 C4 C7 C22 129.67(14) . . . . ? C3 C4 C7 C22 -55.39(16) . . . . ? C11 C3 C8 C16 -1.39(18) . . . . ? C4 C3 C8 C16 178.70(12) . . . . ? C4 C2 C9 C21 -48.8(2) . . . . ? C6 C2 C9 C21 133.26(14) . . . . ? C4 C2 C9 C10 132.76(14) . . . . ? C6 C2 C9 C10 -45.20(17) . . . . ? C21 C9 C10 C15 2.4(2) . . . . ? C2 C9 C10 C15 -179.07(13) . . . . ? C8 C3 C11 C17 1.42(18) . . . . ? C4 C3 C11 C17 -178.67(11) . . . . ? C22 C7 C12 C13 -0.19(19) . . . . ? C4 C7 C12 C13 -175.59(12) . . . . ? C7 C12 C13 C23 -0.3(2) . . . . ? C24 C6 C14 C34 -1.5(2) . . . . ? C2 C6 C14 C34 179.95(13) . . . . ? C9 C10 C15 C18 -1.8(2) . . . . ? C3 C8 C16 C19 0.19(19) . . . . ? C3 C11 C17 C19 -0.22(19) . . . . ? C10 C15 C18 C30 -0.3(2) . . . . ? C10 C15 C18 C26 179.47(14) . . . . ? C11 C17 C19 C16 -1.01(19) . . . . ? C8 C16 C19 C17 1.0(2) . . . . ? C10 C9 C21 C30 -1.0(2) . . . . ? C2 C9 C21 C30 -179.48(14) . . . . ? C23 C20 C22 C7 -1.86(19) . . . . ? C12 C7 C22 C20 1.28(18) . . . . ? C4 C7 C22 C20 176.64(11) . . . . ? C22 C20 C23 C13 1.29(18) . . . . ? C22 C20 C23 C31 -178.17(12) . . . . ? C12 C13 C23 C20 -0.23(19) . . . . ? C12 C13 C23 C31 179.26(12) . . . . ? C14 C6 C24 C32 1.8(2) . . . . ? C2 C6 C24 C32 -179.63(13) . . . . ? C9 C21 C30 C18 -1.0(2) . . . . ? C15 C18 C30 C21 1.7(2) . . . . ? C26 C18 C30 C21 -178.09(15) . . . . ? C34 C28 C32 C24 -0.8(2) . . . . ? C6 C24 C32 C28 -0.7(2) . . . . ? C32 C28 C34 C14 1.1(2) . . . . ? C6 C14 C34 C28 0.1(2) . . . . ? O2 C33 C35 C27 61.32(19) . . . . ? C25 C29 C36 O1 66.58(18) . . . . ? _database_code_depnum_ccdc_archive 'CCDC 932687' ####################################################################### # # 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_global # The following lines are used to test the character set of files sent by # network email or other means. They are not part of the CIF data set # abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789 # !@#$%^&*()_+{}:"~<>?|\-=[];'`,./ # END of CIF # Attachment 'trans-DATPE.cif' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# data_2 _chemical_name_systematic ; ? ; _chemical_formula_sum 'C34.50 H29 Cl O2' _chemical_formula_moiety "C34 H28 O2', 0.5(C H2 Cl2)" _chemical_formula_weight 511.03 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.33039(18) _cell_length_b 11.2433(4) _cell_length_c 13.3555(3) _cell_angle_alpha 99.498(2) _cell_angle_beta 91.6021(19) _cell_angle_gamma 107.191(2) _cell_volume 1315.72(6) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 9611 _cell_measurement_theta_min 1.5479 _cell_measurement_theta_max 28.0564 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.3219 _exptl_crystal_size_mid 0.2118 _exptl_crystal_size_min 0.0524 _exptl_crystal_density_diffrn 1.29 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 538 loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 0 0 -1 0.0262 0 0 1 0.0262 6 11 -3 0.1059 -6 -11 3 0.1059 -1 1 0 0.1313 -1 1 2 0.0669 -1 -1 2 0.0835 0 -2 1 0.1279 2 -1 0 0.1539 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.176 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET) (compiled Oct 27 2011,15:02:11) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_absorpt_correction_T_min 0.83514 _exptl_absorpt_correction_T_max 1 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'SuperNova (Mo) X-ray Source' _diffrn_radiation_monochromator mirror _diffrn_detector_area_resol_mean 16.0965 _diffrn_orient_matrix_ub_11 0.0307422 _diffrn_orient_matrix_ub_12 0.0657908 _diffrn_orient_matrix_ub_13 0.0002661 _diffrn_orient_matrix_ub_21 0.0038294 _diffrn_orient_matrix_ub_22 0.0120718 _diffrn_orient_matrix_ub_23 0.0539946 _diffrn_orient_matrix_ub_31 0.0735854 _diffrn_orient_matrix_ub_32 -0.0059304 _diffrn_orient_matrix_ub_33 0.0018528 _diffrn_measurement_device_type 'SuperNova, Single source at offset), Eos' _diffrn_measurement_method '\w scans' _diffrn_reflns_av_R_equivalents 0.0404 _diffrn_reflns_av_unetI/netI 0.0326 _diffrn_reflns_number 28043 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.55 _diffrn_reflns_theta_max 28.12 _diffrn_reflns_theta_full 26.5 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.93 _reflns_number_total 5974 _reflns_number_gt 4555 _reflns_threshold_expression >2\s(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET) (compiled Oct 27 2011,15:02:11) ; _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET) (compiled Oct 27 2011,15:02:11) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET) (compiled Oct 27 2011,15:02:11) ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^ > 2\s(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^)+(0.1102P)^2^+0.8897P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 5974 _refine_ls_number_parameters 354 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0842 _refine_ls_R_factor_gt 0.0648 _refine_ls_wR_factor_ref 0.2163 _refine_ls_wR_factor_gt 0.1988 _refine_ls_goodness_of_fit_ref 1.083 _refine_ls_restrained_S_all 1.084 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.353 _refine_diff_density_min -0.834 _refine_diff_density_rms 0.07 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 0.3888(2) 0.2265(2) 0.06452(16) 0.0273(5) Uani 1 1 d . . . C2 C 0.3274(3) 0.3193(2) 0.10895(17) 0.0312(5) Uani 1 1 d . . . H2 H 0.2917 0.3668 0.0672 0.037 Uiso 1 1 calc R . . C3 C 0.3177(3) 0.3433(2) 0.21319(17) 0.0330(5) Uani 1 1 d . . . H3 H 0.2786 0.4089 0.2424 0.04 Uiso 1 1 calc R . . C4 C 0.3650(2) 0.2718(2) 0.27573(16) 0.0307(5) Uani 1 1 d . . . C5 C 0.4201(3) 0.1749(2) 0.23081(17) 0.0325(5) Uani 1 1 d . . . H5 H 0.449 0.1231 0.2719 0.039 Uiso 1 1 calc R . . C6 C 0.4332(3) 0.1533(2) 0.12648(17) 0.0302(5) Uani 1 1 d . . . H6 H 0.4727 0.088 0.0971 0.036 Uiso 1 1 calc R . . C7 C 0.3590(3) 0.3016(3) 0.38416(18) 0.0383(6) Uani 1 1 d . . . C8 C 0.3583(3) 0.3336(3) 0.47385(18) 0.0397(6) Uani 1 1 d . . . C9 C 0.3595(3) 0.3738(3) 0.58420(18) 0.0441(7) Uani 1 1 d . . . H9A H 0.4651 0.4056 0.6141 0.053 Uiso 1 1 calc R . . H9B H 0.3072 0.2994 0.6143 0.053 Uiso 1 1 calc R . . C10 C 0.2849(3) 0.4760(3) 0.61270(19) 0.0415(6) Uani 1 1 d . . . H10A H 0.3003 0.5069 0.6872 0.05 Uiso 1 1 calc R . . H10B H 0.3305 0.5483 0.5784 0.05 Uiso 1 1 calc R . . C11 C 0.5719(2) 0.2289(2) -0.19380(16) 0.0266(4) Uani 1 1 d . . . C12 C 0.6897(3) 0.3235(2) -0.22195(18) 0.0355(5) Uani 1 1 d . . . H12 H 0.745 0.3932 -0.1714 0.043 Uiso 1 1 calc R . . C13 C 0.7282(3) 0.3187(2) -0.32121(18) 0.0357(5) Uani 1 1 d . . . H13 H 0.8082 0.3852 -0.3381 0.043 Uiso 1 1 calc R . . C14 C 0.6509(2) 0.2173(2) -0.39649(17) 0.0296(5) Uani 1 1 d . . . C15 C 0.5332(3) 0.1221(2) -0.36935(18) 0.0351(5) Uani 1 1 d . . . H15 H 0.4787 0.0521 -0.4199 0.042 Uiso 1 1 calc R . . C16 C 0.4943(3) 0.1279(2) -0.26978(18) 0.0321(5) Uani 1 1 d . . . H16 H 0.4134 0.0619 -0.2531 0.038 Uiso 1 1 calc R . . C17 C 0.6955(3) 0.2137(2) -0.49920(18) 0.0335(5) Uani 1 1 d . . . C18 C 0.7406(3) 0.2146(2) -0.58218(18) 0.0345(5) Uani 1 1 d . . . C19 C 0.8051(3) 0.2180(3) -0.68076(18) 0.0384(6) Uani 1 1 d . . . H19A H 0.7646 0.2719 -0.7179 0.046 Uiso 1 1 calc R . . H19B H 0.774 0.1314 -0.7217 0.046 Uiso 1 1 calc R . . C20 C 0.9762(3) 0.2692(3) -0.6699(2) 0.0399(6) Uani 1 1 d . . . H20A H 1.017 0.2182 -0.6297 0.048 Uiso 1 1 calc R . . H20B H 1.0147 0.2609 -0.7382 0.048 Uiso 1 1 calc R . . C21 C 0.2592(2) 0.1682(2) -0.11351(16) 0.0265(4) Uani 1 1 d . . . C22 C 0.1484(3) 0.0593(2) -0.09987(18) 0.0332(5) Uani 1 1 d . . . H22 H 0.1675 0.0113 -0.0517 0.04 Uiso 1 1 calc R . . C23 C 0.0091(3) 0.0200(3) -0.15661(19) 0.0395(6) Uani 1 1 d . . . H23 H -0.0655 -0.055 -0.1474 0.047 Uiso 1 1 calc R . . C24 C -0.0204(3) 0.0896(3) -0.2258(2) 0.0447(6) Uani 1 1 d . . . H24 H -0.1151 0.0627 -0.2644 0.054 Uiso 1 1 calc R . . C25 C 0.0880(3) 0.1984(3) -0.2387(2) 0.0457(6) Uani 1 1 d . . . H25 H 0.0676 0.2471 -0.2859 0.055 Uiso 1 1 calc R . . C26 C 0.2266(3) 0.2371(2) -0.18324(18) 0.0335(5) Uani 1 1 d . . . H26 H 0.3005 0.3121 -0.1931 0.04 Uiso 1 1 calc R . . C27 C 0.6828(2) 0.2913(2) -0.01237(16) 0.0274(5) Uani 1 1 d . . . C28 C 0.7145(3) 0.4048(2) 0.05590(18) 0.0335(5) Uani 1 1 d . . . H28 H 0.6423 0.4494 0.0628 0.04 Uiso 1 1 calc R . . C29 C 0.8513(3) 0.4534(3) 0.1142(2) 0.0414(6) Uani 1 1 d . . . H29 H 0.8724 0.5315 0.1604 0.05 Uiso 1 1 calc R . . C30 C 0.9560(3) 0.3897(3) 0.1056(2) 0.0445(6) Uani 1 1 d . . . H30 H 1.049 0.4231 0.1462 0.053 Uiso 1 1 calc R . . C31 C 0.9265(3) 0.2765(3) 0.0376(2) 0.0438(6) Uani 1 1 d . . . H31 H 0.9991 0.2323 0.0315 0.053 Uiso 1 1 calc R . . C32 C 0.7906(3) 0.2280(2) -0.02138(19) 0.0342(5) Uani 1 1 d . . . H32 H 0.7709 0.1507 -0.0685 0.041 Uiso 1 1 calc R . . C33 C 0.4045(2) 0.2105(2) -0.04848(17) 0.0279(5) Uani 1 1 d . . . C34 C 0.5422(2) 0.2398(2) -0.08382(16) 0.0276(5) Uani 1 1 d . . . O1 O 0.1282(2) 0.42545(19) 0.58233(14) 0.0425(4) Uani 1 1 d . . . H1 H 0.0854 0.4802 0.602 0.064 Uiso 1 1 calc R . . O2 O 1.02705(18) 0.39877(16) -0.62093(13) 0.0362(4) Uani 1 1 d . . . H2A H 1.0604 0.4039 -0.5608 0.054 Uiso 1 1 calc R . . C35 C -0.0234(7) 0.0567(7) 0.4944(6) 0.0671(19) Uani 0.5 1 d PD A -1 H35A H -0.0363 0.062 0.4216 0.081 Uiso 0.5 1 calc PR A -1 H35B H -0.0099 0.1416 0.5356 0.081 Uiso 0.5 1 calc PR A -1 Cl1 Cl -0.1878(2) -0.0575(2) 0.52944(18) 0.0743(5) Uani 0.5 1 d PD A -1 Cl2 Cl 0.1317(3) 0.0081(2) 0.51636(18) 0.0782(6) Uani 0.5 1 d PD A -1 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 0.0242(10) 0.0307(11) 0.0263(10) 0.0047(8) 0.0066(8) 0.0071(8) C2 0.0325(11) 0.0384(13) 0.0271(11) 0.0076(9) 0.0053(9) 0.0162(10) C3 0.0318(11) 0.0425(13) 0.0292(11) 0.0034(10) 0.0058(9) 0.0197(10) C4 0.0244(10) 0.0436(13) 0.0246(10) 0.0046(9) 0.0032(8) 0.0118(9) C5 0.0321(11) 0.0399(13) 0.0290(11) 0.0097(10) 0.0028(9) 0.0143(10) C6 0.0307(11) 0.0314(12) 0.0312(11) 0.0049(9) 0.0075(9) 0.0136(9) C7 0.0341(12) 0.0570(16) 0.0300(12) 0.0075(11) 0.0030(9) 0.0234(12) C8 0.0397(13) 0.0601(17) 0.0273(12) 0.0073(11) 0.0037(10) 0.0275(12) C9 0.0498(15) 0.0669(19) 0.0246(11) 0.0055(11) 0.0032(10) 0.0327(14) C10 0.0386(13) 0.0564(17) 0.0299(12) 0.0001(11) 0.0023(10) 0.0195(12) C11 0.0276(10) 0.0256(11) 0.0271(11) 0.0035(8) 0.0067(8) 0.0091(8) C12 0.0387(13) 0.0311(12) 0.0281(11) 0.0009(9) 0.0033(9) -0.0001(10) C13 0.0327(12) 0.0351(13) 0.0343(12) 0.0085(10) 0.0079(9) 0.0014(10) C14 0.0286(11) 0.0345(12) 0.0289(11) 0.0067(9) 0.0092(8) 0.0131(9) C15 0.0347(12) 0.0308(12) 0.0318(12) -0.0048(9) 0.0094(9) 0.0029(10) C16 0.0313(11) 0.0264(11) 0.0339(12) 0.0018(9) 0.0118(9) 0.0029(9) C17 0.0301(11) 0.0380(13) 0.0328(12) 0.0055(10) 0.0085(9) 0.0110(10) C18 0.0288(11) 0.0386(13) 0.0324(12) 0.0032(10) 0.0056(9) 0.0062(10) C19 0.0345(12) 0.0457(15) 0.0266(11) 0.0007(10) 0.0075(9) 0.0021(11) C20 0.0339(12) 0.0411(14) 0.0379(13) -0.0013(11) 0.0105(10) 0.0050(10) C21 0.0233(10) 0.0320(11) 0.0241(10) 0.0019(8) 0.0047(8) 0.0093(9) C22 0.0338(12) 0.0340(12) 0.0298(11) 0.0052(9) 0.0072(9) 0.0074(10) C23 0.0284(12) 0.0413(14) 0.0388(13) -0.0024(11) 0.0065(10) 0.0005(10) C24 0.0290(12) 0.0597(18) 0.0403(14) 0.0009(12) -0.0031(10) 0.0109(12) C25 0.0421(14) 0.0578(18) 0.0399(14) 0.0123(12) -0.0023(11) 0.0181(13) C26 0.0305(11) 0.0390(13) 0.0317(12) 0.0104(10) 0.0030(9) 0.0097(10) C27 0.0253(10) 0.0298(11) 0.0272(10) 0.0060(9) 0.0053(8) 0.0077(9) C28 0.0309(11) 0.0324(12) 0.0352(12) 0.0016(9) 0.0057(9) 0.0085(9) C29 0.0422(14) 0.0336(13) 0.0391(13) -0.0011(10) -0.0048(11) 0.0022(11) C30 0.0291(12) 0.0439(15) 0.0534(16) 0.0100(12) -0.0086(11) 0.0009(11) C31 0.0280(12) 0.0424(15) 0.0623(17) 0.0115(13) 0.0010(11) 0.0119(11) C32 0.0293(11) 0.0332(12) 0.0388(12) 0.0025(10) 0.0031(9) 0.0099(10) C33 0.0287(11) 0.0277(11) 0.0280(11) 0.0048(8) 0.0048(8) 0.0093(9) C34 0.0284(11) 0.0267(11) 0.0277(11) 0.0034(8) 0.0041(8) 0.0090(9) O1 0.0369(9) 0.0519(11) 0.0400(10) 0.0025(8) 0.0041(7) 0.0185(8) O2 0.0305(8) 0.0383(10) 0.0352(9) 0.0022(7) 0.0003(7) 0.0065(7) C35 0.038(3) 0.062(4) 0.090(5) 0.018(4) 0.000(3) -0.006(3) Cl1 0.0684(12) 0.0730(13) 0.0777(13) 0.0122(10) -0.0070(10) 0.0178(10) Cl2 0.0769(15) 0.0864(15) 0.0878(15) 0.0356(12) 0.0194(12) 0.0377(12) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 1.392(3) . ? C1 C6 1.393(3) . ? C1 C33 1.507(3) . ? C2 C3 1.384(3) . ? C2 H2 0.95 . ? C3 C4 1.396(3) . ? C3 H3 0.95 . ? C4 C5 1.395(3) . ? C4 C7 1.438(3) . ? C5 C6 1.389(3) . ? C5 H5 0.95 . ? C6 H6 0.95 . ? C7 C8 1.193(3) . ? C8 C9 1.467(3) . ? C9 C10 1.514(4) . ? C9 H9A 0.99 . ? C9 H9B 0.99 . ? C10 O1 1.423(3) . ? C10 H10A 0.99 . ? C10 H10B 0.99 . ? C11 C16 1.392(3) . ? C11 C12 1.394(3) . ? C11 C34 1.494(3) . ? C12 C13 1.380(3) . ? C12 H12 0.95 . ? C13 C14 1.388(3) . ? C13 H13 0.95 . ? C14 C15 1.392(3) . ? C14 C17 1.442(3) . ? C15 C16 1.385(3) . ? C15 H15 0.95 . ? C16 H16 0.95 . ? C17 C18 1.197(3) . ? C18 C19 1.464(3) . ? C19 C20 1.522(3) . ? C19 H19A 0.99 . ? C19 H19B 0.99 . ? C20 O2 1.427(3) . ? C20 H20A 0.99 . ? C20 H20B 0.99 . ? C21 C26 1.386(3) . ? C21 C22 1.392(3) . ? C21 C33 1.495(3) . ? C22 C23 1.398(3) . ? C22 H22 0.95 . ? C23 C24 1.376(4) . ? C23 H23 0.95 . ? C24 C25 1.377(4) . ? C24 H24 0.95 . ? C25 C26 1.385(3) . ? C25 H25 0.95 . ? C26 H26 0.95 . ? C27 C28 1.387(3) . ? C27 C32 1.392(3) . ? C27 C34 1.505(3) . ? C28 C29 1.387(3) . ? C28 H28 0.95 . ? C29 C30 1.369(4) . ? C29 H29 0.95 . ? C30 C31 1.384(4) . ? C30 H30 0.95 . ? C31 C32 1.385(3) . ? C31 H31 0.95 . ? C32 H32 0.95 . ? C33 C34 1.348(3) . ? O1 H1 0.84 . ? O2 H2A 0.84 . ? C35 Cl2 1.725(7) . ? C35 Cl1 1.815(7) . ? C35 H35A 0.99 . ? C35 H35B 0.99 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C6 118.6(2) . . ? C2 C1 C33 118.24(19) . . ? C6 C1 C33 123.20(19) . . ? C3 C2 C1 120.9(2) . . ? C3 C2 H2 119.5 . . ? C1 C2 H2 119.5 . . ? C2 C3 C4 120.5(2) . . ? C2 C3 H3 119.7 . . ? C4 C3 H3 119.7 . . ? C5 C4 C3 118.6(2) . . ? C5 C4 C7 121.9(2) . . ? C3 C4 C7 119.5(2) . . ? C6 C5 C4 120.6(2) . . ? C6 C5 H5 119.7 . . ? C4 C5 H5 119.7 . . ? C5 C6 C1 120.7(2) . . ? C5 C6 H6 119.7 . . ? C1 C6 H6 119.7 . . ? C8 C7 C4 176.1(3) . . ? C7 C8 C9 179.3(3) . . ? C8 C9 C10 113.4(2) . . ? C8 C9 H9A 108.9 . . ? C10 C9 H9A 108.9 . . ? C8 C9 H9B 108.9 . . ? C10 C9 H9B 108.9 . . ? H9A C9 H9B 107.7 . . ? O1 C10 C9 109.3(2) . . ? O1 C10 H10A 109.8 . . ? C9 C10 H10A 109.8 . . ? O1 C10 H10B 109.8 . . ? C9 C10 H10B 109.8 . . ? H10A C10 H10B 108.3 . . ? C16 C11 C12 117.5(2) . . ? C16 C11 C34 124.5(2) . . ? C12 C11 C34 117.99(19) . . ? C13 C12 C11 121.8(2) . . ? C13 C12 H12 119.1 . . ? C11 C12 H12 119.1 . . ? C12 C13 C14 120.4(2) . . ? C12 C13 H13 119.8 . . ? C14 C13 H13 119.8 . . ? C13 C14 C15 118.3(2) . . ? C13 C14 C17 119.2(2) . . ? C15 C14 C17 122.5(2) . . ? C16 C15 C14 121.0(2) . . ? C16 C15 H15 119.5 . . ? C14 C15 H15 119.5 . . ? C15 C16 C11 121.0(2) . . ? C15 C16 H16 119.5 . . ? C11 C16 H16 119.5 . . ? C18 C17 C14 176.3(3) . . ? C17 C18 C19 176.5(2) . . ? C18 C19 C20 112.5(2) . . ? C18 C19 H19A 109.1 . . ? C20 C19 H19A 109.1 . . ? C18 C19 H19B 109.1 . . ? C20 C19 H19B 109.1 . . ? H19A C19 H19B 107.8 . . ? O2 C20 C19 111.4(2) . . ? O2 C20 H20A 109.3 . . ? C19 C20 H20A 109.3 . . ? O2 C20 H20B 109.3 . . ? C19 C20 H20B 109.3 . . ? H20A C20 H20B 108 . . ? C26 C21 C22 118.3(2) . . ? C26 C21 C33 122.6(2) . . ? C22 C21 C33 119.0(2) . . ? C21 C22 C23 120.5(2) . . ? C21 C22 H22 119.8 . . ? C23 C22 H22 119.8 . . ? C24 C23 C22 120.2(2) . . ? C24 C23 H23 119.9 . . ? C22 C23 H23 119.9 . . ? C23 C24 C25 119.6(2) . . ? C23 C24 H24 120.2 . . ? C25 C24 H24 120.2 . . ? C24 C25 C26 120.4(3) . . ? C24 C25 H25 119.8 . . ? C26 C25 H25 119.8 . . ? C25 C26 C21 121.1(2) . . ? C25 C26 H26 119.5 . . ? C21 C26 H26 119.5 . . ? C28 C27 C32 118.8(2) . . ? C28 C27 C34 122.6(2) . . ? C32 C27 C34 118.4(2) . . ? C27 C28 C29 120.3(2) . . ? C27 C28 H28 119.8 . . ? C29 C28 H28 119.8 . . ? C30 C29 C28 120.4(2) . . ? C30 C29 H29 119.8 . . ? C28 C29 H29 119.8 . . ? C29 C30 C31 120.0(2) . . ? C29 C30 H30 120 . . ? C31 C30 H30 120 . . ? C30 C31 C32 119.8(2) . . ? C30 C31 H31 120.1 . . ? C32 C31 H31 120.1 . . ? C31 C32 C27 120.6(2) . . ? C31 C32 H32 119.7 . . ? C27 C32 H32 119.7 . . ? C34 C33 C21 124.9(2) . . ? C34 C33 C1 120.14(19) . . ? C21 C33 C1 114.89(17) . . ? C33 C34 C11 125.0(2) . . ? C33 C34 C27 121.3(2) . . ? C11 C34 C27 113.66(18) . . ? C10 O1 H1 109.5 . . ? C20 O2 H2A 109.5 . . ? Cl2 C35 Cl1 108.3(4) . . ? Cl2 C35 H35A 110 . . ? Cl1 C35 H35A 110 . . ? Cl2 C35 H35B 110 . . ? Cl1 C35 H35B 110 . . ? H35A C35 H35B 108.4 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 3.4(3) . . . . ? C33 C1 C2 C3 -176.4(2) . . . . ? C1 C2 C3 C4 -2.1(4) . . . . ? C2 C3 C4 C5 -0.9(4) . . . . ? C2 C3 C4 C7 177.8(2) . . . . ? C3 C4 C5 C6 2.5(3) . . . . ? C7 C4 C5 C6 -176.1(2) . . . . ? C4 C5 C6 C1 -1.2(4) . . . . ? C2 C1 C6 C5 -1.7(3) . . . . ? C33 C1 C6 C5 178.0(2) . . . . ? C5 C4 C7 C8 128(4) . . . . ? C3 C4 C7 C8 -50(4) . . . . ? C4 C7 C8 C9 -5E1(3) . . . . ? C7 C8 C9 C10 11E1(3) . . . . ? C8 C9 C10 O1 66.6(3) . . . . ? C16 C11 C12 C13 0.5(4) . . . . ? C34 C11 C12 C13 177.8(2) . . . . ? C11 C12 C13 C14 -0.9(4) . . . . ? C12 C13 C14 C15 0.7(4) . . . . ? C12 C13 C14 C17 -178.8(2) . . . . ? C13 C14 C15 C16 -0.2(4) . . . . ? C17 C14 C15 C16 179.3(2) . . . . ? C14 C15 C16 C11 -0.2(4) . . . . ? C12 C11 C16 C15 0.0(3) . . . . ? C34 C11 C16 C15 -177.1(2) . . . . ? C13 C14 C17 C18 29(4) . . . . ? C15 C14 C17 C18 -151(4) . . . . ? C14 C17 C18 C19 16(8) . . . . ? C17 C18 C19 C20 -6(5) . . . . ? C18 C19 C20 O2 -65.1(3) . . . . ? C26 C21 C22 C23 1.0(3) . . . . ? C33 C21 C22 C23 177.5(2) . . . . ? C21 C22 C23 C24 -0.7(4) . . . . ? C22 C23 C24 C25 -0.1(4) . . . . ? C23 C24 C25 C26 0.7(4) . . . . ? C24 C25 C26 C21 -0.3(4) . . . . ? C22 C21 C26 C25 -0.5(3) . . . . ? C33 C21 C26 C25 -176.8(2) . . . . ? C32 C27 C28 C29 -0.3(3) . . . . ? C34 C27 C28 C29 -174.6(2) . . . . ? C27 C28 C29 C30 -0.5(4) . . . . ? C28 C29 C30 C31 0.7(4) . . . . ? C29 C30 C31 C32 -0.1(4) . . . . ? C30 C31 C32 C27 -0.6(4) . . . . ? C28 C27 C32 C31 0.8(4) . . . . ? C34 C27 C32 C31 175.4(2) . . . . ? C26 C21 C33 C34 -54.2(3) . . . . ? C22 C21 C33 C34 129.6(2) . . . . ? C26 C21 C33 C1 122.4(2) . . . . ? C22 C21 C33 C1 -53.9(3) . . . . ? C2 C1 C33 C34 112.5(2) . . . . ? C6 C1 C33 C34 -67.3(3) . . . . ? C2 C1 C33 C21 -64.3(3) . . . . ? C6 C1 C33 C21 116.0(2) . . . . ? C21 C33 C34 C11 -3.1(4) . . . . ? C1 C33 C34 C11 -179.5(2) . . . . ? C21 C33 C34 C27 175.2(2) . . . . ? C1 C33 C34 C27 -1.2(3) . . . . ? C16 C11 C34 C33 -42.0(3) . . . . ? C12 C11 C34 C33 140.9(2) . . . . ? C16 C11 C34 C27 139.6(2) . . . . ? C12 C11 C34 C27 -37.5(3) . . . . ? C28 C27 C34 C33 -61.4(3) . . . . ? C32 C27 C34 C33 124.2(2) . . . . ? C28 C27 C34 C11 117.0(2) . . . . ? C32 C27 C34 C11 -57.4(3) . . . . ? # The following lines are used to test the character set of files sent by # network email or other means. They are not part of the CIF data set # abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789 # !@#$%^&*()_+{}:"~<>?|\-=[];'`,./ # END of CIF _database_code_depnum_ccdc_archive 'CCDC 932688'