# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_email vrawal@uchicago.edu _publ_contact_author_name 'Vikram Bhat' loop_ _publ_author_name 'Vikram Bhat' V.Rawal data_bhat07x _database_code_depnum_ccdc_archive 'CCDC 829858' #TrackingRef '- chloride16.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C44 H52 Cl2 N2 O4' _chemical_formula_weight 743.78 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting ? _symmetry_space_group_name_H-M P21 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 9.746(3) _cell_length_b 13.298(4) _cell_length_c 15.127(5) _cell_angle_alpha 90.00 _cell_angle_beta 106.377(5) _cell_angle_gamma 90.00 _cell_volume 1880.9(11) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.48 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.313 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 792 _exptl_absorpt_coefficient_mu 0.219 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9020 _exptl_absorpt_correction_T_max 0.9741 _exptl_absorpt_process_details ; absorption corrections were made based on correspondance of equivalent intensities usingprogram SADABS (G. Sheldrick, Bruker Analytical X-ray Systems, Madison, WI) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 15755 _diffrn_reflns_av_R_equivalents 0.1331 _diffrn_reflns_av_sigmaI/netI 0.1763 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.40 _diffrn_reflns_theta_max 23.60 _reflns_number_total 5546 _reflns_number_gt 3028 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0634P)^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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.18(13) _refine_ls_number_reflns 5546 _refine_ls_number_parameters 480 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1319 _refine_ls_R_factor_gt 0.0771 _refine_ls_wR_factor_ref 0.1771 _refine_ls_wR_factor_gt 0.1571 _refine_ls_goodness_of_fit_ref 0.925 _refine_ls_restrained_S_all 0.925 _refine_ls_shift/su_max 0.058 _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 C1 C 0.0991(9) 0.4398(6) 0.2643(5) 0.055(3) Uani 1 1 d . . . H1A H 0.0776 0.4746 0.2048 0.083 Uiso 1 1 calc R . . H1B H 0.0155 0.4426 0.2881 0.083 Uiso 1 1 calc R . . H1C H 0.1229 0.3694 0.2562 0.083 Uiso 1 1 calc R . . C2 C 0.2206(8) 0.5443(6) 0.4047(5) 0.034(2) Uani 1 1 d . . . H2 H 0.1373 0.5597 0.4228 0.041 Uiso 1 1 calc R . . C3 C 0.3543(8) 0.5756(5) 0.4514(5) 0.033(2) Uani 1 1 d . . . C4 C 0.4437(9) 0.5412(5) 0.3994(5) 0.036(2) Uani 1 1 d . . . C5 C 0.3562(10) 0.4837(6) 0.3243(5) 0.040(2) Uani 1 1 d . . . C6 C 0.4096(11) 0.4339(6) 0.2592(6) 0.053(3) Uani 1 1 d . . . H6 H 0.3486 0.3988 0.2085 0.064 Uiso 1 1 calc R . . C7 C 0.5567(10) 0.4387(6) 0.2729(6) 0.052(2) Uani 1 1 d . . . H7 H 0.5992 0.4038 0.2325 0.063 Uiso 1 1 calc R . . C8 C 0.6421(9) 0.4949(6) 0.3459(5) 0.044(2) Uani 1 1 d . . . H8 H 0.7415 0.4979 0.3512 0.053 Uiso 1 1 calc R . . C9 C 0.5958(9) 0.5451(6) 0.4095(5) 0.038(2) Uani 1 1 d . . . C10 C 0.7043(8) 0.5977(6) 0.4887(5) 0.041(2) Uani 1 1 d . . . C11 C 0.8218(10) 0.5217(7) 0.5157(6) 0.053(3) Uani 1 1 d . . . H11 H 0.7993 0.4584 0.5373 0.064 Uiso 1 1 calc R . . C12 C 0.6467(9) 0.5986(8) 0.5751(6) 0.048(2) Uani 1 1 d . . . C13 C 0.5351(9) 0.6791(6) 0.5761(6) 0.051(2) Uani 1 1 d . . . H13 H 0.5471 0.6908 0.6431 0.062 Uiso 1 1 calc R . . C14 C 0.3772(8) 0.6345(6) 0.5390(6) 0.042(2) Uani 1 1 d . . . C15 C 0.2675(9) 0.7197(7) 0.5271(6) 0.062(3) Uani 1 1 d . . . H15A H 0.2765 0.7648 0.4778 0.094 Uiso 1 1 calc R . . H15B H 0.2852 0.7575 0.5849 0.094 Uiso 1 1 calc R . . H15C H 0.1709 0.6912 0.5111 0.094 Uiso 1 1 calc R . . C16 C 0.3552(9) 0.5637(6) 0.6145(5) 0.048(2) Uani 1 1 d . . . H16A H 0.2633 0.5289 0.5919 0.071 Uiso 1 1 calc R . . H16B H 0.3556 0.6030 0.6694 0.071 Uiso 1 1 calc R . . H16C H 0.4327 0.5141 0.6304 0.071 Uiso 1 1 calc R . . C17 C 0.5717(11) 0.7738(9) 0.5437(7) 0.077(3) Uani 1 1 d . . . H17 H 0.5545 0.8336 0.5734 0.093 Uiso 1 1 calc R . . C18 C 0.6339(9) 0.7820(7) 0.4675(6) 0.048(2) Uani 1 1 d . . . H18 H 0.6788 0.8501 0.4714 0.057 Uiso 1 1 calc R . . C19 C 0.7496(9) 0.7059(6) 0.4698(6) 0.048(2) Uani 1 1 d . . . C20 C 0.8005(10) 0.7107(6) 0.3826(5) 0.052(2) Uani 1 1 d . . . H20A H 0.8822 0.6641 0.3901 0.063 Uiso 1 1 calc R . . H20B H 0.7223 0.6866 0.3297 0.063 Uiso 1 1 calc R . . C21 C 0.8461(11) 0.8148(6) 0.3598(7) 0.075(3) Uani 1 1 d . . . H21A H 0.7773 0.8649 0.3685 0.113 Uiso 1 1 calc R . . H21B H 0.8491 0.8161 0.2956 0.113 Uiso 1 1 calc R . . H21C H 0.9412 0.8303 0.4006 0.113 Uiso 1 1 calc R . . C22 C 0.8726(8) 0.7398(7) 0.5573(6) 0.057(3) Uani 1 1 d . . . H22A H 0.8830 0.8131 0.5567 0.085 Uiso 1 1 calc R . . H22B H 0.9628 0.7080 0.5561 0.085 Uiso 1 1 calc R . . H22C H 0.8482 0.7194 0.6132 0.085 Uiso 1 1 calc R . . C23 C 1.4653(8) 0.6650(6) 1.1587(5) 0.050(2) Uani 1 1 d . . . H23A H 1.5438 0.6407 1.1357 0.075 Uiso 1 1 calc R . . H23B H 1.4682 0.6305 1.2164 0.075 Uiso 1 1 calc R . . H23C H 1.4753 0.7376 1.1696 0.075 Uiso 1 1 calc R . . C24 C 1.3081(8) 0.6211(5) 1.0012(5) 0.036(2) Uani 1 1 d . . . H24 H 1.3827 0.6121 0.9728 0.043 Uiso 1 1 calc R . . C25 C 1.1660(8) 0.6121(6) 0.9564(5) 0.037(2) Uani 1 1 d . . . C26 C 1.0929(8) 0.6378(5) 1.0259(5) 0.033(2) Uani 1 1 d . . . C27 C 1.1968(8) 0.6579(6) 1.1062(5) 0.0308(19) Uani 1 1 d . . . C28 C 1.1683(9) 0.6821(5) 1.1863(6) 0.043(2) Uani 1 1 d . . . H28 H 1.2427 0.6938 1.2413 0.051 Uiso 1 1 calc R . . C29 C 1.0242(10) 0.6890(6) 1.1840(6) 0.044(2) Uani 1 1 d . . . H29 H 1.0000 0.7069 1.2385 0.052 Uiso 1 1 calc R . . C30 C 0.9200(9) 0.6709(5) 1.1071(6) 0.037(2) Uani 1 1 d . . . H30 H 0.8237 0.6778 1.1087 0.044 Uiso 1 1 calc R . . C31 C 0.9459(8) 0.6418(5) 1.0222(5) 0.034(2) Uani 1 1 d . . . C32 C 0.8205(8) 0.6203(6) 0.9378(5) 0.032(2) Uani 1 1 d . . . C33 C 0.7128(9) 0.7090(6) 0.9410(6) 0.045(2) Uani 1 1 d . . . H33 H 0.7495 0.7756 0.9455 0.055 Uiso 1 1 calc R . . C34 C 0.7542(8) 0.5131(6) 0.9340(5) 0.034(2) Uani 1 1 d . . . C35 C 0.7070(9) 0.4894(6) 1.0196(6) 0.048(2) Uani 1 1 d . . . H35A H 0.6413 0.5431 1.0278 0.057 Uiso 1 1 calc R . . H35B H 0.7922 0.4910 1.0739 0.057 Uiso 1 1 calc R . . C36 C 0.6318(10) 0.3872(6) 1.0177(6) 0.058(3) Uani 1 1 d . . . H36A H 0.5462 0.3849 0.9648 0.088 Uiso 1 1 calc R . . H36B H 0.6042 0.3786 1.0748 0.088 Uiso 1 1 calc R . . H36C H 0.6971 0.3330 1.0123 0.088 Uiso 1 1 calc R . . C37 C 0.6188(8) 0.5055(6) 0.8460(5) 0.045(2) Uani 1 1 d . . . H37A H 0.6441 0.5307 0.7918 0.067 Uiso 1 1 calc R . . H37B H 0.5405 0.5459 0.8561 0.067 Uiso 1 1 calc R . . H37C H 0.5884 0.4351 0.8359 0.067 Uiso 1 1 calc R . . C38 C 0.8550(8) 0.4350(6) 0.9161(5) 0.038(2) Uani 1 1 d . . . H38 H 0.7983 0.3714 0.9011 0.045 Uiso 1 1 calc R . . C39 C 0.9114(9) 0.4565(7) 0.8337(6) 0.051(2) Uani 1 1 d . . . H39A H 0.8389 0.4326 0.7778 0.062 Uiso 1 1 calc R . . H39B H 0.9981 0.4150 0.8406 0.062 Uiso 1 1 calc R . . C40 C 0.9493(8) 0.5648(6) 0.8161(5) 0.040(2) Uani 1 1 d . . . H40 H 0.9236 0.5725 0.7476 0.048 Uiso 1 1 calc R . . C41 C 1.1145(8) 0.5957(6) 0.8536(5) 0.036(2) Uani 1 1 d . . . C42 C 1.2034(8) 0.5129(7) 0.8236(6) 0.056(3) Uani 1 1 d . . . H42A H 1.3019 0.5363 0.8337 0.085 Uiso 1 1 calc R . . H42B H 1.1614 0.4980 0.7581 0.085 Uiso 1 1 calc R . . H42C H 1.2030 0.4520 0.8599 0.085 Uiso 1 1 calc R . . C43 C 1.1339(8) 0.6953(6) 0.8057(5) 0.051(2) Uani 1 1 d . . . H43A H 1.0888 0.7503 0.8304 0.076 Uiso 1 1 calc R . . H43B H 1.0890 0.6893 0.7392 0.076 Uiso 1 1 calc R . . H43C H 1.2361 0.7093 0.8170 0.076 Uiso 1 1 calc R . . C44 C 0.8585(9) 0.6395(6) 0.8487(6) 0.040(2) Uani 1 1 d . . . Cl1 Cl 0.4875(3) 0.7798(2) 0.36441(18) 0.0787(9) Uani 1 1 d . . . Cl2 Cl 1.0030(2) 0.40746(15) 1.01797(15) 0.0491(6) Uani 1 1 d . . . N1 N 0.2196(7) 0.4882(5) 0.3291(4) 0.0374(17) Uani 1 1 d . . . N2 N 1.3291(6) 0.6442(5) 1.0905(4) 0.0366(17) Uani 1 1 d . . . O1 O 0.9461(7) 0.5344(5) 0.5123(4) 0.0637(18) Uani 1 1 d . . . H1 H 0.9710 0.4853 0.4855 0.096 Uiso 1 1 calc R . . O2 O 0.6868(6) 0.5358(5) 0.6346(4) 0.0578(18) Uani 1 1 d . . . O3 O 0.5907(6) 0.6995(4) 0.9383(4) 0.0556(17) Uani 1 1 d . . . O4 O 0.8120(6) 0.7118(4) 0.8014(4) 0.0497(15) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.061(6) 0.049(6) 0.044(6) -0.001(5) -0.003(5) -0.012(5) C2 0.027(5) 0.035(5) 0.046(5) -0.004(4) 0.019(4) 0.003(4) C3 0.038(5) 0.032(5) 0.027(5) -0.006(4) 0.006(4) 0.001(4) C4 0.059(6) 0.015(4) 0.034(5) 0.000(4) 0.011(5) -0.013(4) C5 0.055(6) 0.029(5) 0.030(5) 0.005(4) 0.002(4) -0.005(4) C6 0.075(7) 0.038(6) 0.040(5) -0.010(4) 0.007(5) 0.004(5) C7 0.074(7) 0.047(6) 0.040(5) 0.001(5) 0.023(5) 0.024(5) C8 0.044(6) 0.050(6) 0.036(5) 0.009(5) 0.008(4) -0.004(5) C9 0.046(6) 0.028(5) 0.034(5) -0.006(4) 0.003(4) 0.005(4) C10 0.029(5) 0.050(6) 0.041(5) 0.007(4) 0.006(4) 0.007(4) C11 0.055(7) 0.058(6) 0.055(6) 0.006(5) 0.029(5) -0.009(5) C12 0.032(5) 0.072(7) 0.043(6) -0.023(5) 0.012(5) -0.010(5) C13 0.070(7) 0.047(6) 0.044(6) -0.017(5) 0.027(5) -0.011(5) C14 0.032(5) 0.041(6) 0.054(6) 0.007(4) 0.016(4) -0.011(4) C15 0.060(7) 0.048(6) 0.089(7) -0.023(5) 0.036(6) 0.009(5) C16 0.046(6) 0.053(6) 0.042(5) -0.011(5) 0.009(4) 0.002(5) C17 0.085(8) 0.055(7) 0.110(9) 0.008(7) 0.057(7) 0.008(6) C18 0.056(6) 0.041(5) 0.044(6) -0.003(5) 0.012(5) -0.001(5) C19 0.054(6) 0.033(5) 0.062(6) -0.001(5) 0.023(5) 0.002(5) C20 0.069(6) 0.054(6) 0.043(5) 0.010(5) 0.031(5) 0.002(5) C21 0.099(9) 0.038(6) 0.111(9) 0.019(6) 0.064(7) 0.005(6) C22 0.038(6) 0.066(7) 0.069(7) 0.007(5) 0.019(5) -0.007(5) C23 0.038(5) 0.061(6) 0.048(6) -0.006(5) 0.006(5) 0.001(5) C24 0.035(5) 0.040(5) 0.030(5) 0.003(4) 0.007(4) 0.006(4) C25 0.031(5) 0.031(5) 0.040(5) 0.003(4) -0.002(4) 0.002(4) C26 0.035(5) 0.024(5) 0.040(5) 0.003(4) 0.010(4) 0.000(4) C27 0.031(5) 0.030(4) 0.032(5) 0.007(4) 0.010(4) -0.002(4) C28 0.050(6) 0.031(5) 0.048(6) -0.006(4) 0.016(5) -0.009(4) C29 0.064(7) 0.028(5) 0.042(6) 0.001(4) 0.021(5) -0.001(5) C30 0.060(6) 0.020(4) 0.043(6) 0.001(4) 0.034(5) 0.001(4) C31 0.035(5) 0.032(5) 0.037(5) 0.012(4) 0.016(4) 0.010(4) C32 0.032(5) 0.032(5) 0.032(5) 0.002(4) 0.008(4) 0.005(4) C33 0.032(5) 0.035(5) 0.067(6) 0.015(5) 0.010(5) 0.015(4) C34 0.045(5) 0.029(5) 0.038(5) 0.006(4) 0.027(4) 0.000(4) C35 0.045(6) 0.037(5) 0.067(6) -0.011(5) 0.024(5) -0.011(5) C36 0.098(8) 0.027(5) 0.065(6) 0.001(4) 0.048(6) -0.005(5) C37 0.038(5) 0.053(6) 0.045(5) 0.008(5) 0.016(4) -0.008(5) C38 0.040(5) 0.036(5) 0.032(5) -0.001(4) 0.003(4) 0.002(4) C39 0.054(6) 0.052(6) 0.052(6) 0.004(5) 0.021(5) 0.004(5) C40 0.032(5) 0.043(5) 0.042(5) 0.001(4) 0.006(4) -0.014(4) C41 0.027(5) 0.057(6) 0.025(5) 0.008(4) 0.009(4) 0.002(4) C42 0.030(5) 0.072(7) 0.060(6) -0.031(5) 0.001(4) 0.008(5) C43 0.043(6) 0.063(6) 0.040(5) 0.006(5) 0.003(4) -0.005(5) C44 0.039(5) 0.030(5) 0.048(6) 0.007(4) 0.006(4) 0.004(4) Cl1 0.092(2) 0.0663(18) 0.0746(19) 0.0011(15) 0.0185(16) -0.0017(16) Cl2 0.0535(14) 0.0368(12) 0.0531(14) 0.0015(11) 0.0088(12) 0.0041(12) N1 0.032(4) 0.041(4) 0.033(4) 0.003(3) -0.002(4) -0.002(4) N2 0.030(4) 0.043(4) 0.037(4) 0.005(3) 0.008(3) 0.003(3) O1 0.062(5) 0.047(4) 0.083(5) 0.006(4) 0.023(4) 0.012(4) O2 0.039(4) 0.082(5) 0.046(4) 0.023(4) 0.002(3) 0.005(3) O3 0.029(4) 0.048(4) 0.094(5) 0.010(3) 0.025(3) 0.011(3) O4 0.040(4) 0.043(4) 0.070(4) 0.018(3) 0.023(3) 0.009(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 C1 N1 1.451(9) . ? C2 C3 1.360(10) . ? C2 N1 1.363(9) . ? C3 C4 1.404(10) . ? C3 C14 1.501(10) . ? C4 C5 1.434(10) . ? C4 C9 1.448(11) . ? C5 N1 1.355(10) . ? C5 C6 1.404(11) . ? C6 C7 1.391(11) . ? C7 C8 1.397(11) . ? C8 C9 1.350(10) . ? C9 C10 1.526(10) . ? C10 C11 1.497(11) . ? C10 C19 1.554(11) . ? C10 C12 1.560(11) . ? C11 O1 1.238(9) . ? C12 O2 1.210(10) . ? C12 C13 1.529(12) . ? C13 C17 1.433(13) . ? C13 C14 1.596(11) . ? C14 C15 1.533(11) . ? C14 C16 1.542(10) . ? C17 C18 1.451(11) . ? C18 C19 1.509(11) . ? C18 Cl1 1.793(8) . ? C19 C20 1.536(11) . ? C19 C22 1.580(11) . ? C20 C21 1.522(11) . ? C23 N2 1.459(9) . ? C24 N2 1.345(9) . ? C24 C25 1.365(10) . ? C25 C26 1.467(10) . ? C25 C41 1.509(10) . ? C26 C27 1.371(10) . ? C26 C31 1.418(10) . ? C27 C28 1.355(10) . ? C27 N2 1.387(9) . ? C28 C29 1.399(11) . ? C29 C30 1.333(10) . ? C30 C31 1.431(10) . ? C31 C32 1.524(10) . ? C32 C44 1.517(10) . ? C32 C34 1.560(10) . ? C32 C33 1.589(10) . ? C33 O3 1.185(8) . ? C34 C38 1.505(10) . ? C34 C35 1.524(10) . ? C34 C37 1.591(10) . ? C35 C36 1.541(11) . ? C38 C39 1.525(10) . ? C38 Cl2 1.826(7) . ? C39 C40 1.529(11) . ? C40 C44 1.503(11) . ? C40 C41 1.602(10) . ? C41 C42 1.546(10) . ? C41 C43 1.547(11) . ? C44 O4 1.208(9) . ? 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 N1 112.5(7) . . ? C2 C3 C4 105.4(7) . . ? C2 C3 C14 120.0(7) . . ? C4 C3 C14 134.6(7) . . ? C3 C4 C5 107.0(7) . . ? C3 C4 C9 135.1(7) . . ? C5 C4 C9 117.7(8) . . ? N1 C5 C6 128.5(8) . . ? N1 C5 C4 108.0(7) . . ? C6 C5 C4 123.6(9) . . ? C7 C6 C5 116.4(8) . . ? C6 C7 C8 120.1(8) . . ? C9 C8 C7 125.7(8) . . ? C8 C9 C4 116.5(7) . . ? C8 C9 C10 119.3(8) . . ? C4 C9 C10 124.1(7) . . ? C11 C10 C9 102.2(7) . . ? C11 C10 C19 116.1(7) . . ? C9 C10 C19 116.7(7) . . ? C11 C10 C12 101.8(7) . . ? C9 C10 C12 109.1(7) . . ? C19 C10 C12 109.6(7) . . ? O1 C11 C10 125.3(9) . . ? O2 C12 C13 123.8(8) . . ? O2 C12 C10 120.1(8) . . ? C13 C12 C10 116.0(8) . . ? C17 C13 C12 111.5(8) . . ? C17 C13 C14 121.0(8) . . ? C12 C13 C14 110.8(7) . . ? C3 C14 C15 110.9(7) . . ? C3 C14 C16 108.6(6) . . ? C15 C14 C16 107.4(7) . . ? C3 C14 C13 113.2(6) . . ? C15 C14 C13 109.7(7) . . ? C16 C14 C13 106.7(6) . . ? C13 C17 C18 122.5(10) . . ? C17 C18 C19 114.1(8) . . ? C17 C18 Cl1 106.4(7) . . ? C19 C18 Cl1 114.5(6) . . ? C18 C19 C20 111.9(7) . . ? C18 C19 C10 112.1(7) . . ? C20 C19 C10 112.0(7) . . ? C18 C19 C22 102.3(7) . . ? C20 C19 C22 110.8(7) . . ? C10 C19 C22 107.3(7) . . ? C21 C20 C19 114.7(8) . . ? N2 C24 C25 111.3(7) . . ? C24 C25 C26 104.8(7) . . ? C24 C25 C41 121.3(7) . . ? C26 C25 C41 133.2(7) . . ? C27 C26 C31 120.9(7) . . ? C27 C26 C25 107.1(7) . . ? C31 C26 C25 132.0(7) . . ? C28 C27 C26 123.5(8) . . ? C28 C27 N2 128.2(7) . . ? C26 C27 N2 108.2(7) . . ? C27 C28 C29 116.8(8) . . ? C30 C29 C28 121.5(8) . . ? C29 C30 C31 123.3(8) . . ? C26 C31 C30 114.0(7) . . ? C26 C31 C32 126.1(7) . . ? C30 C31 C32 119.9(7) . . ? C44 C32 C31 111.9(6) . . ? C44 C32 C34 108.8(6) . . ? C31 C32 C34 115.4(6) . . ? C44 C32 C33 103.4(6) . . ? C31 C32 C33 102.5(6) . . ? C34 C32 C33 114.2(6) . . ? O3 C33 C32 125.8(8) . . ? C38 C34 C35 112.2(6) . . ? C38 C34 C32 110.7(6) . . ? C35 C34 C32 112.2(6) . . ? C38 C34 C37 103.6(6) . . ? C35 C34 C37 108.7(6) . . ? C32 C34 C37 109.1(6) . . ? C34 C35 C36 115.0(7) . . ? C34 C38 C39 114.9(6) . . ? C34 C38 Cl2 112.8(5) . . ? C39 C38 Cl2 110.2(6) . . ? C38 C39 C40 118.7(7) . . ? C44 C40 C39 111.8(7) . . ? C44 C40 C41 109.9(6) . . ? C39 C40 C41 116.6(7) . . ? C25 C41 C42 110.8(6) . . ? C25 C41 C43 108.1(6) . . ? C42 C41 C43 108.6(6) . . ? C25 C41 C40 114.3(6) . . ? C42 C41 C40 107.6(6) . . ? C43 C41 C40 107.2(6) . . ? O4 C44 C40 119.3(8) . . ? O4 C44 C32 121.0(8) . . ? C40 C44 C32 119.7(7) . . ? C5 N1 C2 107.1(6) . . ? C5 N1 C1 124.4(7) . . ? C2 N1 C1 128.5(7) . . ? C24 N2 C27 108.5(6) . . ? C24 N2 C23 127.1(7) . . ? C27 N2 C23 123.9(7) . . ? 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 N1 C2 C3 C4 3.0(9) . . . . ? N1 C2 C3 C14 -177.3(7) . . . . ? C2 C3 C4 C5 -3.5(8) . . . . ? C14 C3 C4 C5 176.9(8) . . . . ? C2 C3 C4 C9 -178.0(8) . . . . ? C14 C3 C4 C9 2.4(15) . . . . ? C3 C4 C5 N1 2.9(8) . . . . ? C9 C4 C5 N1 178.5(6) . . . . ? C3 C4 C5 C6 -177.5(7) . . . . ? C9 C4 C5 C6 -1.9(11) . . . . ? N1 C5 C6 C7 -177.7(8) . . . . ? C4 C5 C6 C7 2.8(11) . . . . ? C5 C6 C7 C8 -2.9(12) . . . . ? C6 C7 C8 C9 2.2(13) . . . . ? C7 C8 C9 C4 -1.1(12) . . . . ? C7 C8 C9 C10 176.3(7) . . . . ? C3 C4 C9 C8 175.0(8) . . . . ? C5 C4 C9 C8 0.9(10) . . . . ? C3 C4 C9 C10 -2.3(14) . . . . ? C5 C4 C9 C10 -176.3(7) . . . . ? C8 C9 C10 C11 -42.5(9) . . . . ? C4 C9 C10 C11 134.6(8) . . . . ? C8 C9 C10 C19 85.3(9) . . . . ? C4 C9 C10 C19 -97.5(9) . . . . ? C8 C9 C10 C12 -149.8(8) . . . . ? C4 C9 C10 C12 27.4(10) . . . . ? C9 C10 C11 O1 118.2(9) . . . . ? C19 C10 C11 O1 -10.0(12) . . . . ? C12 C10 C11 O1 -129.0(9) . . . . ? C11 C10 C12 O2 -9.8(10) . . . . ? C9 C10 C12 O2 97.7(9) . . . . ? C19 C10 C12 O2 -133.3(8) . . . . ? C11 C10 C12 C13 172.8(7) . . . . ? C9 C10 C12 C13 -79.7(9) . . . . ? C19 C10 C12 C13 49.3(9) . . . . ? O2 C12 C13 C17 140.8(10) . . . . ? C10 C12 C13 C17 -41.9(10) . . . . ? O2 C12 C13 C14 -81.4(10) . . . . ? C10 C12 C13 C14 95.9(8) . . . . ? C2 C3 C14 C15 -47.4(10) . . . . ? C4 C3 C14 C15 132.2(9) . . . . ? C2 C3 C14 C16 70.4(9) . . . . ? C4 C3 C14 C16 -110.0(10) . . . . ? C2 C3 C14 C13 -171.2(7) . . . . ? C4 C3 C14 C13 8.3(12) . . . . ? C17 C13 C14 C3 86.0(10) . . . . ? C12 C13 C14 C3 -47.2(9) . . . . ? C17 C13 C14 C15 -38.5(11) . . . . ? C12 C13 C14 C15 -171.7(7) . . . . ? C17 C13 C14 C16 -154.6(8) . . . . ? C12 C13 C14 C16 72.2(8) . . . . ? C12 C13 C17 C18 39.0(13) . . . . ? C14 C13 C17 C18 -93.9(11) . . . . ? C13 C17 C18 C19 -43.1(13) . . . . ? C13 C17 C18 Cl1 84.1(10) . . . . ? C17 C18 C19 C20 174.0(8) . . . . ? Cl1 C18 C19 C20 51.1(9) . . . . ? C17 C18 C19 C10 47.3(11) . . . . ? Cl1 C18 C19 C10 -75.6(8) . . . . ? C17 C18 C19 C22 -67.4(9) . . . . ? Cl1 C18 C19 C22 169.7(6) . . . . ? C11 C10 C19 C18 -165.2(7) . . . . ? C9 C10 C19 C18 74.1(9) . . . . ? C12 C10 C19 C18 -50.6(9) . . . . ? C11 C10 C19 C20 68.2(10) . . . . ? C9 C10 C19 C20 -52.6(10) . . . . ? C12 C10 C19 C20 -177.2(7) . . . . ? C11 C10 C19 C22 -53.7(9) . . . . ? C9 C10 C19 C22 -174.4(7) . . . . ? C12 C10 C19 C22 61.0(8) . . . . ? C18 C19 C20 C21 53.0(11) . . . . ? C10 C19 C20 C21 179.8(8) . . . . ? C22 C19 C20 C21 -60.4(10) . . . . ? N2 C24 C25 C26 3.1(9) . . . . ? N2 C24 C25 C41 174.4(7) . . . . ? C24 C25 C26 C27 -1.2(8) . . . . ? C41 C25 C26 C27 -170.9(8) . . . . ? C24 C25 C26 C31 -179.5(8) . . . . ? C41 C25 C26 C31 10.8(15) . . . . ? C31 C26 C27 C28 0.2(12) . . . . ? C25 C26 C27 C28 -178.3(7) . . . . ? C31 C26 C27 N2 177.4(7) . . . . ? C25 C26 C27 N2 -1.1(8) . . . . ? C26 C27 C28 C29 -1.8(12) . . . . ? N2 C27 C28 C29 -178.4(7) . . . . ? C27 C28 C29 C30 1.1(12) . . . . ? C28 C29 C30 C31 1.1(12) . . . . ? C27 C26 C31 C30 1.9(10) . . . . ? C25 C26 C31 C30 179.9(8) . . . . ? C27 C26 C31 C32 -179.4(7) . . . . ? C25 C26 C31 C32 -1.3(13) . . . . ? C29 C30 C31 C26 -2.6(11) . . . . ? C29 C30 C31 C32 178.6(7) . . . . ? C26 C31 C32 C44 -25.8(10) . . . . ? C30 C31 C32 C44 152.8(7) . . . . ? C26 C31 C32 C34 99.3(8) . . . . ? C30 C31 C32 C34 -82.0(8) . . . . ? C26 C31 C32 C33 -136.0(8) . . . . ? C30 C31 C32 C33 42.7(9) . . . . ? C44 C32 C33 O3 116.0(9) . . . . ? C31 C32 C33 O3 -127.6(9) . . . . ? C34 C32 C33 O3 -2.1(12) . . . . ? C44 C32 C34 C38 56.2(8) . . . . ? C31 C32 C34 C38 -70.5(8) . . . . ? C33 C32 C34 C38 171.1(6) . . . . ? C44 C32 C34 C35 -177.6(7) . . . . ? C31 C32 C34 C35 55.7(9) . . . . ? C33 C32 C34 C35 -62.7(8) . . . . ? C44 C32 C34 C37 -57.2(8) . . . . ? C31 C32 C34 C37 176.1(6) . . . . ? C33 C32 C34 C37 57.7(8) . . . . ? C38 C34 C35 C36 -58.3(9) . . . . ? C32 C34 C35 C36 176.3(7) . . . . ? C37 C34 C35 C36 55.7(9) . . . . ? C35 C34 C38 C39 -177.5(7) . . . . ? C32 C34 C38 C39 -51.3(8) . . . . ? C37 C34 C38 C39 65.5(8) . . . . ? C35 C34 C38 Cl2 -50.0(8) . . . . ? C32 C34 C38 Cl2 76.2(7) . . . . ? C37 C34 C38 Cl2 -167.0(5) . . . . ? C34 C38 C39 C40 38.9(10) . . . . ? Cl2 C38 C39 C40 -89.8(8) . . . . ? C38 C39 C40 C44 -30.1(10) . . . . ? C38 C39 C40 C41 97.4(9) . . . . ? C24 C25 C41 C42 46.5(10) . . . . ? C26 C25 C41 C42 -145.2(8) . . . . ? C24 C25 C41 C43 -72.5(9) . . . . ? C26 C25 C41 C43 95.9(10) . . . . ? C24 C25 C41 C40 168.2(7) . . . . ? C26 C25 C41 C40 -23.4(12) . . . . ? C44 C40 C41 C25 52.8(9) . . . . ? C39 C40 C41 C25 -75.6(9) . . . . ? C44 C40 C41 C42 176.3(7) . . . . ? C39 C40 C41 C42 47.8(9) . . . . ? C44 C40 C41 C43 -67.0(8) . . . . ? C39 C40 C41 C43 164.5(7) . . . . ? C39 C40 C44 O4 -138.1(8) . . . . ? C41 C40 C44 O4 90.8(9) . . . . ? C39 C40 C44 C32 38.8(10) . . . . ? C41 C40 C44 C32 -92.3(8) . . . . ? C31 C32 C44 O4 -107.0(8) . . . . ? C34 C32 C44 O4 124.3(8) . . . . ? C33 C32 C44 O4 2.6(10) . . . . ? C31 C32 C44 C40 76.1(9) . . . . ? C34 C32 C44 C40 -52.6(9) . . . . ? C33 C32 C44 C40 -174.3(7) . . . . ? C6 C5 N1 C2 179.3(8) . . . . ? C4 C5 N1 C2 -1.1(8) . . . . ? C6 C5 N1 C1 0.0(12) . . . . ? C4 C5 N1 C1 179.5(6) . . . . ? C3 C2 N1 C5 -1.2(9) . . . . ? C3 C2 N1 C1 178.1(7) . . . . ? C25 C24 N2 C27 -3.9(9) . . . . ? C25 C24 N2 C23 -176.5(7) . . . . ? C28 C27 N2 C24 -179.9(8) . . . . ? C26 C27 N2 C24 3.0(8) . . . . ? C28 C27 N2 C23 -7.1(12) . . . . ? C26 C27 N2 C23 175.9(7) . . . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 23.60 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.287 _refine_diff_density_min -0.503 _refine_diff_density_rms 0.063 # Attachment '- cyclopropane10.cif' data_bhat04s _database_code_depnum_ccdc_archive 'CCDC 829859' #TrackingRef '- cyclopropane10.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H24 Cl N O2' _chemical_formula_weight 369.87 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting ? _symmetry_space_group_name_H-M P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 8.941(4) _cell_length_b 9.465(4) _cell_length_c 22.998(8) _cell_angle_alpha 90.00 _cell_angle_beta 110.502(14) _cell_angle_gamma 90.00 _cell_volume 1823.0(13) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 1024 _cell_measurement_theta_min 1.89 _cell_measurement_theta_max 25.02 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.348 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 784 _exptl_absorpt_coefficient_mu 0.226 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9150 _exptl_absorpt_correction_T_max 0.9647 _exptl_absorpt_process_details ; absorption corrections were made based on correspondance of equivalent intensities usingprogram SADABS (G. Sheldrick, Bruker Analytical X-ray Systems, Madison, WI) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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_reflns_number 3587 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0505 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 1.89 _diffrn_reflns_theta_max 25.02 _reflns_number_total 3699 _reflns_number_gt 3577 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1021P)^2^+2.3488P] 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 3699 _refine_ls_number_parameters 240 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0651 _refine_ls_R_factor_gt 0.0627 _refine_ls_wR_factor_ref 0.1760 _refine_ls_wR_factor_gt 0.1734 _refine_ls_goodness_of_fit_ref 1.093 _refine_ls_restrained_S_all 1.093 _refine_ls_shift/su_max 0.008 _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 C1 C -0.1792(4) -0.1520(4) 0.00551(17) 0.0235(8) Uani 1 1 d . . . H1A H -0.2407 -0.2081 0.0251 0.035 Uiso 1 1 calc R . . H1B H -0.0832 -0.2044 0.0071 0.035 Uiso 1 1 calc R . . H1C H -0.2447 -0.1333 -0.0379 0.035 Uiso 1 1 calc R . . C2 C -0.2247(4) 0.0993(4) 0.02805(15) 0.0187(7) Uani 1 1 d . . . H2 H -0.3277 0.1074 -0.0030 0.022 Uiso 1 1 calc R . . C3 C -0.1501(4) 0.2052(4) 0.06787(16) 0.0177(7) Uani 1 1 d . . . C4 C 0.0022(4) 0.1488(3) 0.10611(15) 0.0166(7) Uani 1 1 d . . . C5 C 0.0059(4) 0.0052(4) 0.08761(16) 0.0181(7) Uani 1 1 d . . . C6 C 0.1300(4) -0.0875(3) 0.11734(16) 0.0189(7) Uani 1 1 d . . . H6 H 0.1282 -0.1826 0.1039 0.023 Uiso 1 1 calc R . . C7 C 0.2551(4) -0.0367(4) 0.16691(17) 0.0230(8) Uani 1 1 d . . . H7 H 0.3391 -0.0985 0.1894 0.028 Uiso 1 1 calc R . . C8 C 0.2601(4) 0.1050(4) 0.18457(16) 0.0200(7) Uani 1 1 d . . . H8 H 0.3498 0.1375 0.2182 0.024 Uiso 1 1 calc R . . C9 C 0.1390(4) 0.2005(4) 0.15486(15) 0.0160(7) Uani 1 1 d . . . C10 C 0.1731(4) 0.3572(3) 0.17129(15) 0.0159(7) Uani 1 1 d . . . C11 C 0.3244(4) 0.3843(4) 0.15629(17) 0.0203(7) Uani 1 1 d . . . H11 H 0.3111 0.4002 0.1140 0.024 Uiso 1 1 calc R . . C12 C 0.0422(4) 0.4575(4) 0.13054(15) 0.0172(7) Uani 1 1 d . . . C13 C -0.1276(4) 0.4304(3) 0.12938(16) 0.0172(7) Uani 1 1 d . . . H13 H -0.1800 0.5245 0.1275 0.021 Uiso 1 1 calc R . . C14 C -0.2230(4) 0.3497(4) 0.06947(16) 0.0187(7) Uani 1 1 d . . . C15 C -0.2298(5) 0.4345(4) 0.01174(17) 0.0251(8) Uani 1 1 d . . . H15A H -0.2994 0.3860 -0.0256 0.038 Uiso 1 1 calc R . . H15B H -0.1221 0.4427 0.0101 0.038 Uiso 1 1 calc R . . H15C H -0.2723 0.5291 0.0139 0.038 Uiso 1 1 calc R . . C16 C -0.3956(4) 0.3309(4) 0.06842(17) 0.0237(8) Uani 1 1 d . . . H16A H -0.3955 0.2674 0.1021 0.036 Uiso 1 1 calc R . . H16B H -0.4620 0.2904 0.0285 0.036 Uiso 1 1 calc R . . H16C H -0.4389 0.4230 0.0740 0.036 Uiso 1 1 calc R . . C17 C -0.1230(4) 0.3582(4) 0.18982(16) 0.0195(7) Uani 1 1 d . . . H17A H -0.2226 0.3800 0.1976 0.023 Uiso 1 1 calc R . . H17B H -0.1174 0.2545 0.1852 0.023 Uiso 1 1 calc R . . C18 C 0.0189(4) 0.4067(4) 0.24459(15) 0.0170(7) Uani 1 1 d . . . H18 H -0.0017 0.4864 0.2693 0.020 Uiso 1 1 calc R . . C19 C 0.1817(4) 0.4079(4) 0.23661(15) 0.0165(7) Uani 1 1 d . . . C20 C 0.2877(4) 0.5341(4) 0.26221(16) 0.0218(7) Uani 1 1 d . . . H20A H 0.3998 0.5044 0.2768 0.033 Uiso 1 1 calc R . . H20B H 0.2624 0.5744 0.2969 0.033 Uiso 1 1 calc R . . H20C H 0.2697 0.6054 0.2295 0.033 Uiso 1 1 calc R . . C21 C 0.1490(4) 0.3040(4) 0.28028(16) 0.0209(7) Uani 1 1 d . . . H21 H 0.1324 0.2041 0.2652 0.025 Uiso 1 1 calc R . . C22 C 0.2217(4) 0.3211(4) 0.34886(17) 0.0250(8) Uani 1 1 d . . . H22A H 0.1550 0.2721 0.3691 0.030 Uiso 1 1 calc R . . H22B H 0.2254 0.4226 0.3596 0.030 Uiso 1 1 calc R . . Cl1 Cl 0.42192(11) 0.24860(11) 0.37728(4) 0.0328(3) Uani 1 1 d . . . N1 N -0.1331(4) -0.0192(3) 0.03836(13) 0.0193(6) Uani 1 1 d . . . O1 O 0.0753(3) 0.5583(3) 0.10553(12) 0.0251(6) Uani 1 1 d . . . O2 O 0.4572(3) 0.3871(3) 0.19286(12) 0.0274(6) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0236(18) 0.0229(17) 0.0249(18) -0.0075(15) 0.0096(15) -0.0066(15) C2 0.0174(17) 0.0243(17) 0.0136(15) -0.0006(14) 0.0046(13) -0.0002(14) C3 0.0149(16) 0.0203(16) 0.0188(17) 0.0031(14) 0.0071(13) 0.0001(13) C4 0.0164(16) 0.0173(15) 0.0169(16) 0.0009(13) 0.0068(13) -0.0014(14) C5 0.0183(17) 0.0209(16) 0.0168(16) -0.0001(13) 0.0082(14) -0.0026(14) C6 0.0203(16) 0.0143(15) 0.0238(17) -0.0024(13) 0.0098(14) -0.0017(14) C7 0.0189(17) 0.0224(17) 0.0287(19) 0.0032(15) 0.0097(15) 0.0062(14) C8 0.0150(16) 0.0247(17) 0.0187(16) 0.0011(14) 0.0039(14) 0.0020(15) C9 0.0136(16) 0.0202(16) 0.0153(15) -0.0005(13) 0.0063(13) 0.0000(13) C10 0.0159(15) 0.0189(16) 0.0123(15) -0.0035(13) 0.0044(13) -0.0017(13) C11 0.0219(18) 0.0182(16) 0.0214(17) -0.0061(14) 0.0086(15) -0.0039(14) C12 0.0181(17) 0.0186(16) 0.0142(15) -0.0081(13) 0.0047(13) -0.0025(14) C13 0.0125(15) 0.0135(15) 0.0257(17) 0.0012(14) 0.0069(13) 0.0049(13) C14 0.0144(16) 0.0186(16) 0.0209(17) 0.0009(14) 0.0033(13) 0.0018(13) C15 0.0261(19) 0.0224(17) 0.0215(18) 0.0026(15) 0.0017(15) 0.0018(15) C16 0.0158(16) 0.0258(18) 0.0274(18) -0.0045(15) 0.0049(14) 0.0032(15) C17 0.0169(16) 0.0197(16) 0.0230(17) -0.0021(14) 0.0084(14) -0.0008(14) C18 0.0169(16) 0.0214(16) 0.0170(16) 0.0001(14) 0.0113(13) 0.0013(14) C19 0.0116(15) 0.0201(16) 0.0169(16) -0.0026(13) 0.0037(13) 0.0021(13) C20 0.0231(17) 0.0190(17) 0.0225(17) -0.0068(14) 0.0070(14) -0.0013(15) C21 0.0195(17) 0.0222(17) 0.0204(18) -0.0023(14) 0.0062(14) -0.0009(14) C22 0.0205(17) 0.0297(19) 0.0244(19) 0.0001(15) 0.0073(15) 0.0020(16) Cl1 0.0227(5) 0.0403(5) 0.0292(5) 0.0073(4) 0.0012(4) 0.0041(4) N1 0.0202(14) 0.0206(14) 0.0180(14) -0.0025(12) 0.0077(12) -0.0025(12) O1 0.0265(13) 0.0180(12) 0.0270(13) 0.0019(10) 0.0047(11) -0.0053(11) O2 0.0155(12) 0.0377(15) 0.0289(14) -0.0078(12) 0.0077(11) -0.0046(11) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N1 1.450(5) . ? C2 N1 1.360(5) . ? C2 C3 1.363(5) . ? C3 C4 1.440(5) . ? C3 C14 1.521(5) . ? C4 C9 1.425(5) . ? C4 C5 1.429(5) . ? C5 N1 1.377(5) . ? C5 C6 1.391(5) . ? C6 C7 1.375(5) . ? C7 C8 1.397(5) . ? C8 C9 1.392(5) . ? C9 C10 1.535(5) . ? C10 C11 1.530(5) . ? C10 C12 1.543(5) . ? C10 C19 1.553(4) . ? C11 O2 1.191(4) . ? C12 O1 1.203(4) . ? C12 C13 1.531(4) . ? C13 C17 1.537(5) . ? C13 C14 1.545(5) . ? C14 C15 1.535(5) . ? C14 C16 1.545(5) . ? C17 C18 1.513(5) . ? C18 C21 1.517(5) . ? C18 C19 1.530(4) . ? C19 C21 1.506(5) . ? C19 C20 1.510(5) . ? C21 C22 1.489(5) . ? C22 Cl1 1.812(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 C2 C3 111.5(3) . . ? C2 C3 C4 105.9(3) . . ? C2 C3 C14 124.3(3) . . ? C4 C3 C14 129.8(3) . . ? C9 C4 C5 117.2(3) . . ? C9 C4 C3 136.1(3) . . ? C5 C4 C3 106.6(3) . . ? N1 C5 C6 129.3(3) . . ? N1 C5 C4 107.2(3) . . ? C6 C5 C4 123.5(3) . . ? C7 C6 C5 117.6(3) . . ? C6 C7 C8 120.7(3) . . ? C9 C8 C7 122.7(3) . . ? C8 C9 C4 118.0(3) . . ? C8 C9 C10 116.9(3) . . ? C4 C9 C10 124.5(3) . . ? C11 C10 C9 102.8(3) . . ? C11 C10 C12 107.6(3) . . ? C9 C10 C12 113.7(3) . . ? C11 C10 C19 114.7(3) . . ? C9 C10 C19 118.4(3) . . ? C12 C10 C19 99.6(3) . . ? O2 C11 C10 125.9(3) . . ? O1 C12 C13 122.2(3) . . ? O1 C12 C10 121.1(3) . . ? C13 C12 C10 116.4(3) . . ? C12 C13 C17 110.3(3) . . ? C12 C13 C14 109.5(3) . . ? C17 C13 C14 114.7(3) . . ? C3 C14 C15 109.7(3) . . ? C3 C14 C13 111.0(3) . . ? C15 C14 C13 110.8(3) . . ? C3 C14 C16 109.3(3) . . ? C15 C14 C16 108.1(3) . . ? C13 C14 C16 107.9(3) . . ? C18 C17 C13 111.5(3) . . ? C17 C18 C21 121.1(3) . . ? C17 C18 C19 117.3(3) . . ? C21 C18 C19 59.3(2) . . ? C21 C19 C20 119.9(3) . . ? C21 C19 C18 60.0(2) . . ? C20 C19 C18 116.9(3) . . ? C21 C19 C10 119.2(3) . . ? C20 C19 C10 115.7(3) . . ? C18 C19 C10 112.8(3) . . ? C22 C21 C19 121.4(3) . . ? C22 C21 C18 118.1(3) . . ? C19 C21 C18 60.8(2) . . ? C21 C22 Cl1 110.5(3) . . ? C2 N1 C5 108.7(3) . . ? C2 N1 C1 125.5(3) . . ? C5 N1 C1 125.7(3) . . ? 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 N1 C2 C3 C4 0.6(4) . . . . ? N1 C2 C3 C14 -178.2(3) . . . . ? C2 C3 C4 C9 178.0(4) . . . . ? C14 C3 C4 C9 -3.2(7) . . . . ? C2 C3 C4 C5 -2.5(4) . . . . ? C14 C3 C4 C5 176.2(3) . . . . ? C9 C4 C5 N1 -176.9(3) . . . . ? C3 C4 C5 N1 3.5(4) . . . . ? C9 C4 C5 C6 4.5(5) . . . . ? C3 C4 C5 C6 -175.1(3) . . . . ? N1 C5 C6 C7 -178.5(3) . . . . ? C4 C5 C6 C7 -0.3(5) . . . . ? C5 C6 C7 C8 -3.0(5) . . . . ? C6 C7 C8 C9 1.9(6) . . . . ? C7 C8 C9 C4 2.5(5) . . . . ? C7 C8 C9 C10 -169.5(3) . . . . ? C5 C4 C9 C8 -5.4(5) . . . . ? C3 C4 C9 C8 174.0(4) . . . . ? C5 C4 C9 C10 165.9(3) . . . . ? C3 C4 C9 C10 -14.7(6) . . . . ? C8 C9 C10 C11 56.6(4) . . . . ? C4 C9 C10 C11 -114.8(4) . . . . ? C8 C9 C10 C12 172.6(3) . . . . ? C4 C9 C10 C12 1.2(5) . . . . ? C8 C9 C10 C19 -71.0(4) . . . . ? C4 C9 C10 C19 117.6(3) . . . . ? C9 C10 C11 O2 -99.4(4) . . . . ? C12 C10 C11 O2 140.3(4) . . . . ? C19 C10 C11 O2 30.5(5) . . . . ? C11 C10 C12 O1 -16.7(4) . . . . ? C9 C10 C12 O1 -129.8(3) . . . . ? C19 C10 C12 O1 103.3(3) . . . . ? C11 C10 C12 C13 169.4(3) . . . . ? C9 C10 C12 C13 56.3(4) . . . . ? C19 C10 C12 C13 -70.6(3) . . . . ? O1 C12 C13 C17 -147.2(3) . . . . ? C10 C12 C13 C17 26.6(4) . . . . ? O1 C12 C13 C14 85.7(4) . . . . ? C10 C12 C13 C14 -100.5(3) . . . . ? C2 C3 C14 C15 -71.4(4) . . . . ? C4 C3 C14 C15 110.1(4) . . . . ? C2 C3 C14 C13 165.9(3) . . . . ? C4 C3 C14 C13 -12.7(5) . . . . ? C2 C3 C14 C16 46.9(4) . . . . ? C4 C3 C14 C16 -131.6(4) . . . . ? C12 C13 C14 C3 63.0(4) . . . . ? C17 C13 C14 C3 -61.5(4) . . . . ? C12 C13 C14 C15 -59.1(4) . . . . ? C17 C13 C14 C15 176.3(3) . . . . ? C12 C13 C14 C16 -177.2(3) . . . . ? C17 C13 C14 C16 58.2(4) . . . . ? C12 C13 C17 C18 33.2(4) . . . . ? C14 C13 C17 C18 157.3(3) . . . . ? C13 C17 C18 C21 -116.7(3) . . . . ? C13 C17 C18 C19 -47.8(4) . . . . ? C17 C18 C19 C21 -111.7(3) . . . . ? C17 C18 C19 C20 137.7(3) . . . . ? C21 C18 C19 C20 -110.6(3) . . . . ? C17 C18 C19 C10 0.0(4) . . . . ? C21 C18 C19 C10 111.6(3) . . . . ? C11 C10 C19 C21 -124.5(3) . . . . ? C9 C10 C19 C21 -2.8(4) . . . . ? C12 C10 C19 C21 120.9(3) . . . . ? C11 C10 C19 C20 29.9(4) . . . . ? C9 C10 C19 C20 151.7(3) . . . . ? C12 C10 C19 C20 -84.6(3) . . . . ? C11 C10 C19 C18 168.3(3) . . . . ? C9 C10 C19 C18 -70.0(4) . . . . ? C12 C10 C19 C18 53.7(3) . . . . ? C20 C19 C21 C22 -1.2(5) . . . . ? C18 C19 C21 C22 -106.9(4) . . . . ? C10 C19 C21 C22 152.2(3) . . . . ? C20 C19 C21 C18 105.7(3) . . . . ? C10 C19 C21 C18 -100.9(3) . . . . ? C17 C18 C21 C22 -142.5(3) . . . . ? C19 C18 C21 C22 112.2(4) . . . . ? C17 C18 C21 C19 105.3(3) . . . . ? C19 C21 C22 Cl1 -83.3(4) . . . . ? C18 C21 C22 Cl1 -154.5(3) . . . . ? C3 C2 N1 C5 1.6(4) . . . . ? C3 C2 N1 C1 177.9(3) . . . . ? C6 C5 N1 C2 175.3(4) . . . . ? C4 C5 N1 C2 -3.2(4) . . . . ? C6 C5 N1 C1 -1.0(6) . . . . ? C4 C5 N1 C1 -179.4(3) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.02 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.357 _refine_diff_density_min -0.338 _refine_diff_density_rms 0.072 # Attachment '- diene11.cif' data_bhat03r _database_code_depnum_ccdc_archive 'CCDC 829860' #TrackingRef '- diene11.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C44 H46 N2 O4' _chemical_formula_weight 666.83 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting ? _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.579(5) _cell_length_b 10.734(5) _cell_length_c 16.874(8) _cell_angle_alpha 84.784(9) _cell_angle_beta 89.891(9) _cell_angle_gamma 75.579(8) _cell_volume 1673.0(14) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.24 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.324 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 712 _exptl_absorpt_coefficient_mu 0.084 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9768 _exptl_absorpt_correction_T_max 0.9801 _exptl_absorpt_process_details ; absorption corrections were made based on correspondance of equivalent intensities usingprogram SADABS (G. Sheldrick, Bruker Analytical X-ray Systems, Madison, WI) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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_reflns_number 16310 _diffrn_reflns_av_R_equivalents 0.0713 _diffrn_reflns_av_sigmaI/netI 0.0748 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.21 _diffrn_reflns_theta_max 25.11 _reflns_number_total 5935 _reflns_number_gt 4025 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1670P)^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 5935 _refine_ls_number_parameters 459 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1194 _refine_ls_R_factor_gt 0.0938 _refine_ls_wR_factor_ref 0.2498 _refine_ls_wR_factor_gt 0.2320 _refine_ls_goodness_of_fit_ref 0.992 _refine_ls_restrained_S_all 0.992 _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 C1 C 0.2571(4) 0.3823(4) 0.5443(2) 0.0325(9) Uani 1 1 d . . . H1A H 0.1736 0.4142 0.5771 0.049 Uiso 1 1 calc R . . H1B H 0.3449 0.3584 0.5778 0.049 Uiso 1 1 calc R . . H1C H 0.2451 0.3064 0.5195 0.049 Uiso 1 1 calc R . . C2 C 0.3728(4) 0.4690(3) 0.42859(19) 0.0240(8) Uani 1 1 d . . . C3 C 0.4899(4) 0.3660(3) 0.4215(2) 0.0286(8) Uani 1 1 d . . . H3 H 0.5068 0.2907 0.4579 0.034 Uiso 1 1 calc R . . C4 C 0.5804(4) 0.3761(4) 0.3603(2) 0.0322(9) Uani 1 1 d . . . H4 H 0.6625 0.3071 0.3540 0.039 Uiso 1 1 calc R . . C5 C 0.5540(4) 0.4859(3) 0.3072(2) 0.0295(8) Uani 1 1 d . . . H5 H 0.6178 0.4892 0.2643 0.035 Uiso 1 1 calc R . . C6 C 0.4387(4) 0.5907(3) 0.3142(2) 0.0239(8) Uani 1 1 d . . . C7 C 0.3449(4) 0.5840(3) 0.37723(19) 0.0231(8) Uani 1 1 d . . . C8 C 0.2183(4) 0.6677(3) 0.4066(2) 0.0240(8) Uani 1 1 d . . . C9 C 0.1789(4) 0.5999(3) 0.4702(2) 0.0260(8) Uani 1 1 d . . . H9 H 0.0978 0.6319 0.5017 0.031 Uiso 1 1 calc R . . C10 C 0.1401(4) 0.8028(3) 0.3773(2) 0.0256(8) Uani 1 1 d . . . C11 C 0.0043(4) 0.8023(4) 0.3314(2) 0.0311(9) Uani 1 1 d . . . H11A H 0.0299 0.7498 0.2864 0.047 Uiso 1 1 calc R . . H11B H -0.0450 0.8909 0.3114 0.047 Uiso 1 1 calc R . . H11C H -0.0598 0.7657 0.3666 0.047 Uiso 1 1 calc R . . C12 C 0.0949(4) 0.8838(4) 0.4471(2) 0.0354(9) Uani 1 1 d . . . H12A H 0.0225 0.8512 0.4779 0.053 Uiso 1 1 calc R . . H12B H 0.0540 0.9741 0.4269 0.053 Uiso 1 1 calc R . . H12C H 0.1793 0.8780 0.4813 0.053 Uiso 1 1 calc R . . C13 C 0.2386(4) 0.8685(3) 0.3252(2) 0.0268(8) Uani 1 1 d . . . H13 H 0.1809 0.9579 0.3074 0.032 Uiso 1 1 calc R . . C14 C 0.2764(4) 0.7997(3) 0.2521(2) 0.0234(8) Uani 1 1 d . . . C15 C 0.4220(4) 0.7046(3) 0.25160(19) 0.0246(8) Uani 1 1 d . . . C16 C 0.4236(4) 0.6524(4) 0.1703(2) 0.0308(9) Uani 1 1 d . . . H16 H 0.3747 0.5863 0.1661 0.037 Uiso 1 1 calc R . . C17 C 0.5334(4) 0.7791(3) 0.2659(2) 0.0263(8) Uani 1 1 d . . . C18 C 0.6710(4) 0.7473(4) 0.2226(2) 0.0346(9) Uani 1 1 d . . . H18A H 0.6598 0.7989 0.1710 0.052 Uiso 1 1 calc R . . H18B H 0.6965 0.6553 0.2143 0.052 Uiso 1 1 calc R . . H18C H 0.7476 0.7668 0.2540 0.052 Uiso 1 1 calc R . . C19 C 0.5061(4) 0.8645(3) 0.3207(2) 0.0273(8) Uani 1 1 d . . . C20 C 0.6094(4) 0.9353(4) 0.3407(2) 0.0303(8) Uani 1 1 d . . . H20 H 0.6938 0.9229 0.3097 0.036 Uiso 1 1 calc R . . C21 C 0.6009(5) 1.0140(4) 0.3960(3) 0.0427(10) Uani 1 1 d . . . H21A H 0.5191 1.0303 0.4289 0.051 Uiso 1 1 calc R . . H21B H 0.6765 1.0549 0.4033 0.051 Uiso 1 1 calc R . . C22 C 0.3707(4) 0.8820(4) 0.3688(2) 0.0293(8) Uani 1 1 d . . . H22A H 0.3897 0.8176 0.4159 0.035 Uiso 1 1 calc R . . H22B H 0.3493 0.9688 0.3884 0.035 Uiso 1 1 calc R . . C23 C 0.6826(4) 0.6099(4) -0.0455(2) 0.0323(9) Uani 1 1 d . . . H23A H 0.6306 0.6872 -0.0212 0.048 Uiso 1 1 calc R . . H23B H 0.6144 0.5772 -0.0759 0.048 Uiso 1 1 calc R . . H23C H 0.7554 0.6319 -0.0813 0.048 Uiso 1 1 calc R . . C24 C 0.8482(4) 0.5288(3) 0.07088(19) 0.0244(8) Uani 1 1 d . . . C25 C 0.9027(4) 0.6350(3) 0.0772(2) 0.0289(8) Uani 1 1 d . . . H25 H 0.8740 0.7104 0.0411 0.035 Uiso 1 1 calc R . . C26 C 0.9995(4) 0.6269(4) 0.1374(2) 0.0305(8) Uani 1 1 d . . . H26 H 1.0419 0.6969 0.1430 0.037 Uiso 1 1 calc R . . C27 C 1.0368(4) 0.5173(3) 0.1909(2) 0.0286(8) Uani 1 1 d . . . H27 H 1.1012 0.5164 0.2338 0.034 Uiso 1 1 calc R . . C28 C 0.9854(4) 0.4102(3) 0.1849(2) 0.0246(8) Uani 1 1 d . . . C29 C 0.8885(3) 0.4133(3) 0.12159(19) 0.0228(8) Uani 1 1 d . . . C30 C 0.8143(3) 0.3260(3) 0.0921(2) 0.0240(8) Uani 1 1 d . . . C31 C 0.7341(4) 0.3912(3) 0.02938(19) 0.0237(8) Uani 1 1 d . . . H31 H 0.6725 0.3567 -0.0016 0.028 Uiso 1 1 calc R . . C32 C 0.8210(4) 0.1880(3) 0.1212(2) 0.0262(8) Uani 1 1 d . . . C33 C 0.8259(4) 0.1079(4) 0.0499(2) 0.0373(10) Uani 1 1 d . . . H33A H 0.7384 0.1425 0.0169 0.056 Uiso 1 1 calc R . . H33B H 0.8317 0.0178 0.0691 0.056 Uiso 1 1 calc R . . H33C H 0.9106 0.1124 0.0182 0.056 Uiso 1 1 calc R . . C34 C 0.6866(4) 0.1799(4) 0.1677(2) 0.0364(9) Uani 1 1 d . . . H34A H 0.6758 0.2363 0.2110 0.055 Uiso 1 1 calc R . . H34B H 0.6958 0.0906 0.1899 0.055 Uiso 1 1 calc R . . H34C H 0.6018 0.2076 0.1320 0.055 Uiso 1 1 calc R . . C35 C 0.9569(4) 0.1286(3) 0.1725(2) 0.0253(8) Uani 1 1 d . . . H35 H 0.9565 0.0368 0.1888 0.030 Uiso 1 1 calc R . . C36 C 0.9516(3) 0.1951(3) 0.2470(2) 0.0244(8) Uani 1 1 d . . . C37 C 1.0347(4) 0.2975(3) 0.2477(2) 0.0256(8) Uani 1 1 d . . . C38 C 1.0032(4) 0.3479(4) 0.3289(2) 0.0322(9) Uani 1 1 d . . . H38 H 0.9175 0.4142 0.3330 0.039 Uiso 1 1 calc R . . C39 C 1.1914(4) 0.2279(3) 0.2341(2) 0.0255(8) Uani 1 1 d . . . C40 C 1.3059(4) 0.2643(4) 0.2793(2) 0.0347(9) Uani 1 1 d . . . H40A H 1.3235 0.2122 0.3307 0.052 Uiso 1 1 calc R . . H40B H 1.2748 0.3561 0.2881 0.052 Uiso 1 1 calc R . . H40C H 1.3948 0.2488 0.2489 0.052 Uiso 1 1 calc R . . C41 C 1.2163(4) 0.1458(3) 0.1776(2) 0.0259(8) Uani 1 1 d . . . C42 C 1.3626(4) 0.0829(3) 0.1575(2) 0.0281(8) Uani 1 1 d . . . H42 H 1.4373 0.0859 0.1936 0.034 Uiso 1 1 calc R . . C43 C 1.4006(4) 0.0223(4) 0.0939(2) 0.0366(9) Uani 1 1 d . . . H43A H 1.3293 0.0169 0.0561 0.044 Uiso 1 1 calc R . . H43B H 1.4994 -0.0163 0.0855 0.044 Uiso 1 1 calc R . . C44 C 1.0964(4) 0.1263(3) 0.1280(2) 0.0264(8) Uani 1 1 d . . . H44A H 1.1288 0.0422 0.1053 0.032 Uiso 1 1 calc R . . H44B H 1.0758 0.1946 0.0830 0.032 Uiso 1 1 calc R . . N1 N 0.2684(3) 0.4813(3) 0.48376(17) 0.0263(7) Uani 1 1 d . . . N2 N 0.7520(3) 0.5122(3) 0.01581(17) 0.0272(7) Uani 1 1 d . . . O1 O 0.1974(3) 0.8205(2) 0.19422(14) 0.0291(6) Uani 1 1 d . . . O2 O 0.4790(3) 0.6852(3) 0.11179(15) 0.0431(7) Uani 1 1 d . . . O3 O 0.8900(3) 0.1646(2) 0.30522(14) 0.0309(6) Uani 1 1 d . . . O4 O 1.0755(3) 0.3124(3) 0.38749(15) 0.0476(8) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.043(2) 0.034(2) 0.0206(19) 0.0017(16) 0.0035(16) -0.0112(17) C2 0.0309(19) 0.0272(19) 0.0159(17) -0.0050(14) -0.0002(14) -0.0097(15) C3 0.036(2) 0.026(2) 0.0220(19) -0.0014(15) -0.0028(16) -0.0048(16) C4 0.031(2) 0.031(2) 0.032(2) -0.0097(17) 0.0020(16) -0.0009(16) C5 0.0297(19) 0.033(2) 0.025(2) -0.0068(16) 0.0071(15) -0.0053(16) C6 0.0280(18) 0.0274(19) 0.0182(17) -0.0069(14) 0.0029(14) -0.0091(14) C7 0.0289(18) 0.0259(19) 0.0156(17) -0.0068(14) 0.0024(14) -0.0076(14) C8 0.0273(18) 0.0300(19) 0.0157(17) -0.0074(14) 0.0019(14) -0.0070(14) C9 0.0312(19) 0.034(2) 0.0147(17) -0.0095(15) 0.0055(14) -0.0090(16) C10 0.0286(18) 0.0275(19) 0.0209(18) -0.0058(15) 0.0073(15) -0.0058(14) C11 0.031(2) 0.038(2) 0.023(2) -0.0020(16) 0.0094(16) -0.0075(16) C12 0.044(2) 0.033(2) 0.028(2) -0.0116(17) 0.0171(17) -0.0054(17) C13 0.0310(19) 0.030(2) 0.0185(18) -0.0017(15) 0.0034(15) -0.0053(15) C14 0.0262(18) 0.0280(19) 0.0163(17) 0.0012(14) 0.0041(14) -0.0086(14) C15 0.0256(18) 0.036(2) 0.0126(17) -0.0033(14) 0.0041(14) -0.0077(15) C16 0.032(2) 0.041(2) 0.020(2) -0.0071(16) 0.0041(16) -0.0084(16) C17 0.0302(19) 0.032(2) 0.0152(17) -0.0002(15) 0.0026(14) -0.0061(15) C18 0.031(2) 0.048(2) 0.026(2) -0.0030(18) 0.0085(16) -0.0122(17) C19 0.0324(19) 0.032(2) 0.0180(18) 0.0010(15) 0.0018(15) -0.0099(15) C20 0.031(2) 0.032(2) 0.027(2) 0.0000(16) -0.0007(16) -0.0084(16) C21 0.046(2) 0.045(3) 0.043(3) -0.009(2) 0.000(2) -0.021(2) C22 0.037(2) 0.032(2) 0.0210(19) -0.0084(15) 0.0067(16) -0.0117(16) C23 0.044(2) 0.033(2) 0.0169(18) 0.0012(15) 0.0045(16) -0.0038(17) C24 0.0276(18) 0.031(2) 0.0131(17) -0.0060(14) 0.0059(14) -0.0032(15) C25 0.035(2) 0.029(2) 0.0217(19) -0.0023(15) 0.0117(16) -0.0074(16) C26 0.034(2) 0.030(2) 0.031(2) -0.0112(16) 0.0090(16) -0.0119(16) C27 0.0285(19) 0.035(2) 0.0242(19) -0.0108(16) 0.0047(15) -0.0076(16) C28 0.0264(18) 0.031(2) 0.0166(17) -0.0062(14) 0.0081(14) -0.0066(15) C29 0.0251(17) 0.0292(19) 0.0136(17) -0.0052(14) 0.0084(14) -0.0048(14) C30 0.0226(17) 0.033(2) 0.0163(17) -0.0064(15) 0.0056(14) -0.0064(14) C31 0.0256(18) 0.031(2) 0.0161(17) -0.0085(14) 0.0054(14) -0.0080(14) C32 0.0280(18) 0.032(2) 0.0210(18) -0.0079(15) 0.0028(14) -0.0095(15) C33 0.045(2) 0.037(2) 0.032(2) -0.0111(18) -0.0070(18) -0.0110(18) C34 0.032(2) 0.042(2) 0.035(2) 0.0038(18) 0.0009(17) -0.0118(17) C35 0.0286(19) 0.0269(19) 0.0210(19) -0.0025(15) 0.0034(15) -0.0083(15) C36 0.0211(17) 0.029(2) 0.0204(18) -0.0019(15) -0.0005(14) -0.0021(14) C37 0.0279(18) 0.036(2) 0.0138(17) -0.0047(15) 0.0043(14) -0.0095(15) C38 0.036(2) 0.042(2) 0.020(2) -0.0082(17) 0.0090(16) -0.0117(17) C39 0.0282(19) 0.034(2) 0.0157(17) -0.0025(15) 0.0040(14) -0.0105(15) C40 0.030(2) 0.046(2) 0.029(2) -0.0105(18) -0.0007(16) -0.0082(17) C41 0.0261(18) 0.031(2) 0.0208(19) -0.0007(15) 0.0053(15) -0.0074(15) C42 0.0283(19) 0.035(2) 0.0197(18) 0.0009(15) 0.0053(15) -0.0065(15) C43 0.033(2) 0.043(2) 0.035(2) -0.0130(18) 0.0081(17) -0.0073(17) C44 0.0310(19) 0.0277(19) 0.0212(18) -0.0058(15) 0.0051(15) -0.0073(15) N1 0.0357(17) 0.0287(17) 0.0145(14) -0.0010(12) 0.0058(12) -0.0084(13) N2 0.0345(17) 0.0280(17) 0.0162(15) -0.0003(12) 0.0012(12) -0.0030(13) O1 0.0291(13) 0.0392(15) 0.0205(13) -0.0024(11) 0.0024(11) -0.0113(11) O2 0.0425(16) 0.069(2) 0.0189(15) -0.0104(13) 0.0097(12) -0.0147(14) O3 0.0323(14) 0.0423(16) 0.0180(13) 0.0007(11) 0.0094(11) -0.0104(11) O4 0.0463(17) 0.082(2) 0.0159(14) -0.0088(14) 0.0044(13) -0.0174(15) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N1 1.430(4) . ? C2 N1 1.355(4) . ? C2 C3 1.379(5) . ? C2 C7 1.410(5) . ? C3 C4 1.361(5) . ? C4 C5 1.384(5) . ? C5 C6 1.380(5) . ? C6 C7 1.400(5) . ? C6 C15 1.518(5) . ? C7 C8 1.434(5) . ? C8 C9 1.348(5) . ? C8 C10 1.497(5) . ? C9 N1 1.346(5) . ? C10 C11 1.517(5) . ? C10 C12 1.525(5) . ? C10 C13 1.542(5) . ? C13 C14 1.493(5) . ? C13 C22 1.509(5) . ? C14 O1 1.207(4) . ? C14 C15 1.510(5) . ? C15 C17 1.516(5) . ? C15 C16 1.526(5) . ? C16 O2 1.187(4) . ? C17 C19 1.341(5) . ? C17 C18 1.485(5) . ? C19 C20 1.446(5) . ? C19 C22 1.510(5) . ? C20 C21 1.303(5) . ? C23 N2 1.439(4) . ? C24 N2 1.363(4) . ? C24 C25 1.379(5) . ? C24 C29 1.410(5) . ? C25 C26 1.359(5) . ? C26 C27 1.387(5) . ? C27 C28 1.369(5) . ? C28 C29 1.410(5) . ? C28 C37 1.514(5) . ? C29 C30 1.431(5) . ? C30 C31 1.342(5) . ? C30 C32 1.503(5) . ? C31 N2 1.351(4) . ? C32 C34 1.522(5) . ? C32 C35 1.529(5) . ? C32 C33 1.535(5) . ? C35 C36 1.497(5) . ? C35 C44 1.528(5) . ? C36 O3 1.206(4) . ? C36 C37 1.511(5) . ? C37 C38 1.521(5) . ? C37 C39 1.528(5) . ? C38 O4 1.186(4) . ? C39 C41 1.339(5) . ? C39 C40 1.486(5) . ? C41 C42 1.450(5) . ? C41 C44 1.489(5) . ? C42 C43 1.310(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 N1 C2 C3 128.3(3) . . ? N1 C2 C7 108.2(3) . . ? C3 C2 C7 123.4(3) . . ? C4 C3 C2 117.5(3) . . ? C3 C4 C5 120.7(3) . . ? C6 C5 C4 122.5(3) . . ? C5 C6 C7 118.2(3) . . ? C5 C6 C15 117.1(3) . . ? C7 C6 C15 124.8(3) . . ? C6 C7 C2 117.6(3) . . ? C6 C7 C8 136.4(3) . . ? C2 C7 C8 106.0(3) . . ? C9 C8 C7 105.7(3) . . ? C9 C8 C10 124.1(3) . . ? C7 C8 C10 130.2(3) . . ? N1 C9 C8 111.8(3) . . ? C8 C10 C11 110.1(3) . . ? C8 C10 C12 110.5(3) . . ? C11 C10 C12 107.6(3) . . ? C8 C10 C13 110.6(3) . . ? C11 C10 C13 110.8(3) . . ? C12 C10 C13 107.1(3) . . ? C14 C13 C22 112.0(3) . . ? C14 C13 C10 109.6(3) . . ? C22 C13 C10 113.8(3) . . ? O1 C14 C13 122.5(3) . . ? O1 C14 C15 120.2(3) . . ? C13 C14 C15 117.3(3) . . ? C14 C15 C17 106.6(3) . . ? C14 C15 C6 113.2(3) . . ? C17 C15 C6 110.2(3) . . ? C14 C15 C16 103.3(3) . . ? C17 C15 C16 116.2(3) . . ? C6 C15 C16 107.3(3) . . ? O2 C16 C15 127.3(4) . . ? C19 C17 C18 123.4(3) . . ? C19 C17 C15 118.1(3) . . ? C18 C17 C15 118.3(3) . . ? C17 C19 C20 121.8(3) . . ? C17 C19 C22 120.7(3) . . ? C20 C19 C22 117.4(3) . . ? C21 C20 C19 128.0(4) . . ? C13 C22 C19 115.5(3) . . ? N2 C24 C25 128.4(3) . . ? N2 C24 C29 107.3(3) . . ? C25 C24 C29 124.2(3) . . ? C26 C25 C24 117.0(3) . . ? C25 C26 C27 120.5(3) . . ? C28 C27 C26 123.3(3) . . ? C27 C28 C29 117.8(3) . . ? C27 C28 C37 117.7(3) . . ? C29 C28 C37 124.5(3) . . ? C28 C29 C24 117.0(3) . . ? C28 C29 C30 136.5(3) . . ? C24 C29 C30 106.5(3) . . ? C31 C30 C29 106.1(3) . . ? C31 C30 C32 124.4(3) . . ? C29 C30 C32 129.5(3) . . ? C30 C31 N2 111.4(3) . . ? C30 C32 C34 110.3(3) . . ? C30 C32 C35 110.8(3) . . ? C34 C32 C35 110.6(3) . . ? C30 C32 C33 109.7(3) . . ? C34 C32 C33 107.5(3) . . ? C35 C32 C33 107.8(3) . . ? C36 C35 C44 111.6(3) . . ? C36 C35 C32 110.3(3) . . ? C44 C35 C32 113.4(3) . . ? O3 C36 C35 122.0(3) . . ? O3 C36 C37 121.3(3) . . ? C35 C36 C37 116.6(3) . . ? C36 C37 C28 114.5(3) . . ? C36 C37 C38 103.4(3) . . ? C28 C37 C38 108.0(3) . . ? C36 C37 C39 105.3(3) . . ? C28 C37 C39 109.8(3) . . ? C38 C37 C39 115.9(3) . . ? O4 C38 C37 126.1(4) . . ? C41 C39 C40 124.5(3) . . ? C41 C39 C37 117.4(3) . . ? C40 C39 C37 117.9(3) . . ? C39 C41 C42 120.6(3) . . ? C39 C41 C44 121.3(3) . . ? C42 C41 C44 117.8(3) . . ? C43 C42 C41 125.7(4) . . ? C41 C44 C35 114.6(3) . . ? C9 N1 C2 108.2(3) . . ? C9 N1 C1 127.1(3) . . ? C2 N1 C1 124.6(3) . . ? C31 N2 C24 108.6(3) . . ? C31 N2 C23 127.0(3) . . ? C24 N2 C23 124.4(3) . . ? 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 N1 C2 C3 C4 179.7(3) . . . . ? C7 C2 C3 C4 -1.6(5) . . . . ? C2 C3 C4 C5 -0.5(5) . . . . ? C3 C4 C5 C6 1.6(6) . . . . ? C4 C5 C6 C7 -0.6(5) . . . . ? C4 C5 C6 C15 -179.7(3) . . . . ? C5 C6 C7 C2 -1.4(5) . . . . ? C15 C6 C7 C2 177.6(3) . . . . ? C5 C6 C7 C8 178.7(4) . . . . ? C15 C6 C7 C8 -2.3(6) . . . . ? N1 C2 C7 C6 -178.5(3) . . . . ? C3 C2 C7 C6 2.6(5) . . . . ? N1 C2 C7 C8 1.4(4) . . . . ? C3 C2 C7 C8 -177.5(3) . . . . ? C6 C7 C8 C9 179.1(4) . . . . ? C2 C7 C8 C9 -0.8(4) . . . . ? C6 C7 C8 C10 -1.4(7) . . . . ? C2 C7 C8 C10 178.7(3) . . . . ? C7 C8 C9 N1 -0.1(4) . . . . ? C10 C8 C9 N1 -179.6(3) . . . . ? C9 C8 C10 C11 -77.5(4) . . . . ? C7 C8 C10 C11 103.0(4) . . . . ? C9 C8 C10 C12 41.2(5) . . . . ? C7 C8 C10 C12 -138.2(4) . . . . ? C9 C8 C10 C13 159.7(3) . . . . ? C7 C8 C10 C13 -19.8(5) . . . . ? C8 C10 C13 C14 64.3(4) . . . . ? C11 C10 C13 C14 -58.2(4) . . . . ? C12 C10 C13 C14 -175.3(3) . . . . ? C8 C10 C13 C22 -62.0(4) . . . . ? C11 C10 C13 C22 175.6(3) . . . . ? C12 C10 C13 C22 58.4(4) . . . . ? C22 C13 C14 O1 -150.2(3) . . . . ? C10 C13 C14 O1 82.5(4) . . . . ? C22 C13 C14 C15 27.6(4) . . . . ? C10 C13 C14 C15 -99.7(3) . . . . ? O1 C14 C15 C17 120.2(3) . . . . ? C13 C14 C15 C17 -57.7(4) . . . . ? O1 C14 C15 C6 -118.6(3) . . . . ? C13 C14 C15 C6 63.6(4) . . . . ? O1 C14 C15 C16 -2.8(4) . . . . ? C13 C14 C15 C16 179.3(3) . . . . ? C5 C6 C15 C14 166.3(3) . . . . ? C7 C6 C15 C14 -12.8(5) . . . . ? C5 C6 C15 C17 -74.5(4) . . . . ? C7 C6 C15 C17 106.4(4) . . . . ? C5 C6 C15 C16 52.9(4) . . . . ? C7 C6 C15 C16 -126.1(3) . . . . ? C14 C15 C16 O2 98.9(4) . . . . ? C17 C15 C16 O2 -17.4(6) . . . . ? C6 C15 C16 O2 -141.2(4) . . . . ? C14 C15 C17 C19 41.6(4) . . . . ? C6 C15 C17 C19 -81.6(4) . . . . ? C16 C15 C17 C19 156.1(3) . . . . ? C14 C15 C17 C18 -142.6(3) . . . . ? C6 C15 C17 C18 94.3(4) . . . . ? C16 C15 C17 C18 -28.1(5) . . . . ? C18 C17 C19 C20 1.5(6) . . . . ? C15 C17 C19 C20 177.1(3) . . . . ? C18 C17 C19 C22 -173.4(3) . . . . ? C15 C17 C19 C22 2.2(5) . . . . ? C17 C19 C20 C21 -175.1(4) . . . . ? C22 C19 C20 C21 0.0(6) . . . . ? C14 C13 C22 C19 18.5(4) . . . . ? C10 C13 C22 C19 143.5(3) . . . . ? C17 C19 C22 C13 -35.2(5) . . . . ? C20 C19 C22 C13 149.6(3) . . . . ? N2 C24 C25 C26 -179.2(3) . . . . ? C29 C24 C25 C26 -1.3(5) . . . . ? C24 C25 C26 C27 -1.8(5) . . . . ? C25 C26 C27 C28 2.9(5) . . . . ? C26 C27 C28 C29 -0.8(5) . . . . ? C26 C27 C28 C37 -179.8(3) . . . . ? C27 C28 C29 C24 -2.2(4) . . . . ? C37 C28 C29 C24 176.7(3) . . . . ? C27 C28 C29 C30 177.7(4) . . . . ? C37 C28 C29 C30 -3.3(6) . . . . ? N2 C24 C29 C28 -178.4(3) . . . . ? C25 C24 C29 C28 3.3(5) . . . . ? N2 C24 C29 C30 1.7(4) . . . . ? C25 C24 C29 C30 -176.6(3) . . . . ? C28 C29 C30 C31 178.6(4) . . . . ? C24 C29 C30 C31 -1.4(4) . . . . ? C28 C29 C30 C32 -2.4(6) . . . . ? C24 C29 C30 C32 177.6(3) . . . . ? C29 C30 C31 N2 0.7(4) . . . . ? C32 C30 C31 N2 -178.4(3) . . . . ? C31 C30 C32 C34 -77.2(4) . . . . ? C29 C30 C32 C34 103.9(4) . . . . ? C31 C30 C32 C35 160.0(3) . . . . ? C29 C30 C32 C35 -18.9(5) . . . . ? C31 C30 C32 C33 41.0(4) . . . . ? C29 C30 C32 C33 -137.9(4) . . . . ? C30 C32 C35 C36 65.2(4) . . . . ? C34 C32 C35 C36 -57.4(4) . . . . ? C33 C32 C35 C36 -174.7(3) . . . . ? C30 C32 C35 C44 -60.7(4) . . . . ? C34 C32 C35 C44 176.6(3) . . . . ? C33 C32 C35 C44 59.3(4) . . . . ? C44 C35 C36 O3 -148.6(3) . . . . ? C32 C35 C36 O3 84.4(4) . . . . ? C44 C35 C36 C37 28.0(4) . . . . ? C32 C35 C36 C37 -99.0(3) . . . . ? O3 C36 C37 C28 -122.5(3) . . . . ? C35 C36 C37 C28 60.9(4) . . . . ? O3 C36 C37 C38 -5.3(4) . . . . ? C35 C36 C37 C38 178.1(3) . . . . ? O3 C36 C37 C39 116.7(3) . . . . ? C35 C36 C37 C39 -59.9(4) . . . . ? C27 C28 C37 C36 168.3(3) . . . . ? C29 C28 C37 C36 -10.7(5) . . . . ? C27 C28 C37 C38 53.7(4) . . . . ? C29 C28 C37 C38 -125.2(3) . . . . ? C27 C28 C37 C39 -73.5(4) . . . . ? C29 C28 C37 C39 107.6(4) . . . . ? C36 C37 C38 O4 94.5(4) . . . . ? C28 C37 C38 O4 -143.8(4) . . . . ? C39 C37 C38 O4 -20.2(6) . . . . ? C36 C37 C39 C41 44.1(4) . . . . ? C28 C37 C39 C41 -79.7(4) . . . . ? C38 C37 C39 C41 157.7(3) . . . . ? C36 C37 C39 C40 -141.1(3) . . . . ? C28 C37 C39 C40 95.1(4) . . . . ? C38 C37 C39 C40 -27.5(5) . . . . ? C40 C39 C41 C42 1.3(6) . . . . ? C37 C39 C41 C42 175.8(3) . . . . ? C40 C39 C41 C44 -172.4(3) . . . . ? C37 C39 C41 C44 2.1(5) . . . . ? C39 C41 C42 C43 -165.5(4) . . . . ? C44 C41 C42 C43 8.5(6) . . . . ? C39 C41 C44 C35 -37.3(5) . . . . ? C42 C41 C44 C35 148.8(3) . . . . ? C36 C35 C44 C41 20.2(4) . . . . ? C32 C35 C44 C41 145.5(3) . . . . ? C8 C9 N1 C2 1.0(4) . . . . ? C8 C9 N1 C1 -178.0(3) . . . . ? C3 C2 N1 C9 177.4(3) . . . . ? C7 C2 N1 C9 -1.5(4) . . . . ? C3 C2 N1 C1 -3.6(5) . . . . ? C7 C2 N1 C1 177.5(3) . . . . ? C30 C31 N2 C24 0.4(4) . . . . ? C30 C31 N2 C23 -179.3(3) . . . . ? C25 C24 N2 C31 176.9(3) . . . . ? C29 C24 N2 C31 -1.3(4) . . . . ? C25 C24 N2 C23 -3.4(6) . . . . ? C29 C24 N2 C23 178.4(3) . . . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 25.11 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.872 _refine_diff_density_min -0.363 _refine_diff_density_rms 0.135