# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is (c) The Royal Society of Chemistry 2011 data_General _journal_name_full Org.Biomol.Chem. _journal_coden_cambridge 0177 #TrackingRef 'CIF-final-combined.cif' _audit_creation_date 2010-09-01 _audit_creation_method SHELXL-97 _audit_update_record ; ? 2010-09-01 # Formatted by publCIF ; #============================================================================== # PROCESSING SUMMARY (IUCr Office Use Only) _journal_date_recd_electronic ? _journal_date_from_coeditor ? _journal_date_accepted ? _journal_coeditor_code ? #============================================================================== # SUBMISSION DETAILS _publ_contact_author_name 'Jason A. C. Clyburne' _publ_contact_author_email jason.clyburne@smu.ca _publ_contact_author_fax 'ENTER FAX NUMBER' _publ_contact_author_phone 'ENTER PHONE NUMBER' _publ_contact_letter ; ENTER TEXT OF LETTER ; _publ_requested_category 'CHOOSE FI FM FO CI CM CO or AD' _publ_requested_coeditor_name ? #============================================================================== # TITLE AND AUTHOR LIST _publ_section_title ; Three modes of reactivity for anhydrous TEMPO-H: Reactions of a good hydrogen atom donor with low valent carbon centres. ; _publ_section_title_footnote ; ENTER FOOTNOTE TO TITLE OF PAPER ; loop_ _publ_author_name _publ_author_footnote _publ_author_address 'Nicholas A. Giffin' ? ; The Maritimes Center for Green Chemistry Department of Chemistry, Saint Mary's University Halifax, Nova Scotia, B3H 3C3, Canada ; 'Miller Makramalla' ? ; The Maritimes Center for Green Chemistry Department of Chemistry, Saint Mary's University Halifax, Nova Scotia, B3H 3C3, Canada ; 'Arthur D. Hendsbee' ? ; The Maritimes Center for Green Chemistry Department of Chemistry, Saint Mary's University Halifax, Nova Scotia, B3H 3C3, Canada ; 'Katherine N. Robertson' ? ; The Maritimes Center for Green Chemistry Department of Chemistry, Saint Mary's University Halifax, Nova Scotia, B3H 3C3, Canada ; 'Cody Sherren' ? ; The Maritimes Center for Green Chemistry Department of Chemistry, Saint Mary's University Halifax, Nova Scotia, B3H 3C3, Canada ; 'Jason D. Masuda' ? ; The Maritimes Center for Green Chemistry Department of Chemistry, Saint Mary's University Halifax, Nova Scotia, B3H 3C3, Canada ; 'Jason A. C. Clyburne' ? ; The Maritimes Center for Green Chemistry Department of Chemistry, Saint Mary's University Halifax, Nova Scotia, B3H 3C3, Canada ; _publ_section_synopsis ; ENTER SYNOPSIS ; #============================================================================== # TEXT _publ_section_abstract ; ENTER ABSTRACT ; _publ_section_comment ; ENTER TEXT ; _publ_section_references ; ENTER REFERENCES ; _publ_section_figure_captions ; ENTER FIGURE CAPTIONS ; _publ_section_exptl_prep ; ENTER COMPOUND PREPARATION DETAILS ; _publ_section_exptl_refinement ; ENTER SPECIAL DETAILS OF THE REFINEMENT ; #============================================================================== data_anhydrousTEMPO-H _database_code_depnum_ccdc_archive 'CCDC 793072' #TrackingRef 'CIF-final-combined.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C9 H19 N O' _chemical_formula_weight 157.25 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 'trigonal ' _symmetry_space_group_name_H-M 'R-3 ' _symmetry_space_group_name_Hall '-R 3 ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z' '-x+y, -x, z' 'x+2/3, y+1/3, z+1/3' '-y+2/3, x-y+1/3, z+1/3' '-x+y+2/3, -x+1/3, z+1/3' 'x+1/3, y+2/3, z+2/3' '-y+1/3, x-y+2/3, z+2/3' '-x+y+1/3, -x+2/3, z+2/3' '-x, -y, -z' 'y, -x+y, -z' 'x-y, x, -z' '-x+2/3, -y+1/3, -z+1/3' 'y+2/3, -x+y+1/3, -z+1/3' 'x-y+2/3, x+1/3, -z+1/3' '-x+1/3, -y+2/3, -z+2/3' 'y+1/3, -x+y+2/3, -z+2/3' 'x-y+1/3, x+2/3, -z+2/3' _cell_length_a 18.7761(16) _cell_length_b 18.7761(16) _cell_length_c 43.329(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 13229(2) _cell_formula_units_Z 54 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 6637 _cell_measurement_theta_min 2.17 _cell_measurement_theta_max 28.85 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max .3112 _exptl_crystal_size_mid .2925 _exptl_crystal_size_min .2716 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.066 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 4752 _exptl_absorpt_coefficient_mu 0.068 _exptl_absorpt_correction_type Multi-Scan _exptl_absorpt_correction_T_min 0.6486 _exptl_absorpt_correction_T_max 0.7459 _exptl_absorpt_process_details '(SADABS; Bruker 2008)' _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 21413 _diffrn_reflns_av_R_equivalents 0.0471 _diffrn_reflns_av_sigmaI/netI 0.0443 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -51 _diffrn_reflns_limit_l_max 38 _diffrn_reflns_theta_min 2.17 _diffrn_reflns_theta_max 25.00 _reflns_number_total 5195 _reflns_number_gt 3464 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _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^)+(0.0391P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5195 _refine_ls_number_parameters 322 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0781 _refine_ls_R_factor_gt 0.0420 _refine_ls_wR_factor_ref 0.0993 _refine_ls_wR_factor_gt 0.0861 _refine_ls_goodness_of_fit_ref 1.096 _refine_ls_restrained_S_all 1.096 _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 0.43867(9) 0.88770(9) 0.05179(3) 0.0213(4) Uani 1 1 d . . . C2 C 0.44323(10) 0.80825(9) 0.05139(4) 0.0240(4) Uani 1 1 d . . . H2A H 0.3867 0.7605 0.0509 0.029 Uiso 1 1 calc R . . H2B H 0.4717 0.8070 0.0323 0.029 Uiso 1 1 calc R . . C3 C 0.48817(10) 0.80023(10) 0.07917(4) 0.0259(4) Uani 1 1 d . . . H3A H 0.5462 0.8453 0.0791 0.031 Uiso 1 1 calc R . . H3B H 0.4875 0.7472 0.0783 0.031 Uiso 1 1 calc R . . C4 C 0.44589(10) 0.80432(9) 0.10849(4) 0.0254(4) Uani 1 1 d . . . H4A H 0.4761 0.8004 0.1265 0.031 Uiso 1 1 calc R . . H4B H 0.3895 0.7563 0.1091 0.031 Uiso 1 1 calc R . . C5 C 0.44090(9) 0.88321(9) 0.11124(3) 0.0212(4) Uani 1 1 d . . . C6 C 0.52309(9) 0.96321(9) 0.04438(4) 0.0264(4) Uani 1 1 d . . . H6A H 0.5215 1.0136 0.0488 0.040 Uiso 1 1 calc R . . H6B H 0.5359 0.9623 0.0225 0.040 Uiso 1 1 calc R . . H6C H 0.5655 0.9617 0.0571 0.040 Uiso 1 1 calc R . . C7 C 0.37741(10) 0.88183(10) 0.02712(4) 0.0303(4) Uani 1 1 d . . . H7A H 0.3226 0.8359 0.0320 0.046 Uiso 1 1 calc R . . H7B H 0.3948 0.8727 0.0069 0.046 Uiso 1 1 calc R . . H7C H 0.3757 0.9332 0.0267 0.046 Uiso 1 1 calc R . . C8 C 0.52568(10) 0.95751(10) 0.11905(4) 0.0272(4) Uani 1 1 d . . . H8A H 0.5673 0.9583 0.1052 0.041 Uiso 1 1 calc R . . H8B H 0.5399 0.9531 0.1405 0.041 Uiso 1 1 calc R . . H8C H 0.5238 1.0084 0.1165 0.041 Uiso 1 1 calc R . . C9 C 0.38134(10) 0.87241(11) 0.13729(4) 0.0311(4) Uani 1 1 d . . . H9A H 0.3801 0.9236 0.1400 0.047 Uiso 1 1 calc R . . H9B H 0.3996 0.8590 0.1565 0.047 Uiso 1 1 calc R . . H9C H 0.3261 0.8277 0.1321 0.047 Uiso 1 1 calc R . . C10 C 0.13622(9) 0.92369(10) 0.05602(4) 0.0231(4) Uani 1 1 d . . . C11 C 0.04761(9) 0.90668(10) 0.05926(4) 0.0258(4) Uani 1 1 d . . . H11A H 0.0485 0.9598 0.0599 0.031 Uiso 1 1 calc R . . H11B H 0.0159 0.8764 0.0408 0.031 Uiso 1 1 calc R . . C12 C 0.00387(10) 0.85727(10) 0.08790(4) 0.0281(4) Uani 1 1 d . . . H12A H -0.0515 0.8512 0.0894 0.034 Uiso 1 1 calc R . . H12B H -0.0026 0.8017 0.0866 0.034 Uiso 1 1 calc R . . C13 C 0.05399(10) 0.90142(10) 0.11632(4) 0.0270(4) Uani 1 1 d . . . H13A H 0.0263 0.8680 0.1348 0.032 Uiso 1 1 calc R . . H13B H 0.0555 0.9547 0.1185 0.032 Uiso 1 1 calc R . . C14 C 0.14266(10) 0.91737(10) 0.11512(4) 0.0238(4) Uani 1 1 d . . . C15 C 0.17887(10) 0.98814(11) 0.03075(4) 0.0325(4) Uani 1 1 d . . . H15A H 0.1840 1.0404 0.0374 0.049 Uiso 1 1 calc R . . H15B H 0.1463 0.9696 0.0117 0.049 Uiso 1 1 calc R . . H15C H 0.2337 0.9958 0.0269 0.049 Uiso 1 1 calc R . . C16 C 0.13786(10) 0.84560(10) 0.04654(4) 0.0322(4) Uani 1 1 d . . . H16A H 0.1932 0.8540 0.0497 0.048 Uiso 1 1 calc R . . H16B H 0.1230 0.8338 0.0247 0.048 Uiso 1 1 calc R . . H16C H 0.0984 0.7992 0.0591 0.048 Uiso 1 1 calc R . . C17 C 0.14494(11) 0.83738(10) 0.11962(4) 0.0314(4) Uani 1 1 d . . . H17A H 0.1023 0.7938 0.1069 0.047 Uiso 1 1 calc R . . H17B H 0.1350 0.8211 0.1414 0.047 Uiso 1 1 calc R . . H17C H 0.1990 0.8462 0.1135 0.047 Uiso 1 1 calc R . . C18 C 0.19152(11) 0.97562(10) 0.14134(4) 0.0331(4) Uani 1 1 d . . . H18A H 0.2464 0.9815 0.1423 0.050 Uiso 1 1 calc R . . H18B H 0.1628 0.9533 0.1609 0.050 Uiso 1 1 calc R . . H18C H 0.1968 1.0295 0.1377 0.050 Uiso 1 1 calc R . . C19 C 0.44384(10) 0.19759(10) 0.05389(4) 0.0266(4) Uani 1 1 d . . . C20 C 0.37702(10) 0.22182(10) 0.05473(4) 0.0337(5) Uani 1 1 d . . . H20A H 0.3818 0.2542 0.0360 0.040 Uiso 1 1 calc R . . H20B H 0.3223 0.1713 0.0544 0.040 Uiso 1 1 calc R . . C21 C 0.38302(11) 0.27193(11) 0.08310(5) 0.0397(5) Uani 1 1 d . . . H21A H 0.3374 0.2840 0.0831 0.048 Uiso 1 1 calc R . . H21B H 0.4356 0.3248 0.0827 0.048 Uiso 1 1 calc R . . C22 C 0.37857(10) 0.22410(11) 0.11217(4) 0.0351(5) Uani 1 1 d . . . H22A H 0.3239 0.1737 0.1132 0.042 Uiso 1 1 calc R . . H22B H 0.3844 0.2581 0.1305 0.042 Uiso 1 1 calc R . . C23 C 0.44553(10) 0.19994(10) 0.11309(4) 0.0272(4) Uani 1 1 d . . . C24 C 0.52893(10) 0.27252(11) 0.04696(4) 0.0368(5) Uani 1 1 d . . . H24A H 0.5357 0.3201 0.0588 0.055 Uiso 1 1 calc R . . H24B H 0.5333 0.2851 0.0249 0.055 Uiso 1 1 calc R . . H24C H 0.5719 0.2601 0.0529 0.055 Uiso 1 1 calc R . . C25 C 0.42402(11) 0.13382(11) 0.02860(4) 0.0341(4) Uani 1 1 d . . . H25A H 0.4699 0.1232 0.0264 0.051 Uiso 1 1 calc R . . H25B H 0.4155 0.1546 0.0090 0.051 Uiso 1 1 calc R . . H25C H 0.3740 0.0826 0.0341 0.051 Uiso 1 1 calc R . . C26 C 0.53113(10) 0.27533(10) 0.11907(4) 0.0374(5) Uani 1 1 d . . . H26A H 0.5737 0.2627 0.1128 0.056 Uiso 1 1 calc R . . H26B H 0.5371 0.2889 0.1411 0.056 Uiso 1 1 calc R . . H26C H 0.5370 0.3223 0.1071 0.056 Uiso 1 1 calc R . . C27 C 0.42696(11) 0.13799(11) 0.13910(4) 0.0375(5) Uani 1 1 d . . . H27A H 0.3763 0.0866 0.1343 0.056 Uiso 1 1 calc R . . H27B H 0.4200 0.1606 0.1585 0.056 Uiso 1 1 calc R . . H27C H 0.4726 0.1271 0.1411 0.056 Uiso 1 1 calc R . . N1 N 0.40209(7) 0.88946(7) 0.08206(3) 0.0193(3) Uani 1 1 d . . . N2 N 0.17829(8) 0.96283(8) 0.08564(3) 0.0216(3) Uani 1 1 d . . . N3 N 0.43711(8) 0.15470(8) 0.08371(3) 0.0216(3) Uani 1 1 d . . . O1 O 0.40098(7) 0.96606(7) 0.08365(3) 0.0264(3) Uani 1 1 d . . . O2 O 0.26268(7) 0.97813(8) 0.08345(3) 0.0274(3) Uani 1 1 d . . . O3 O 0.50268(7) 0.13435(7) 0.08374(3) 0.0263(3) Uani 1 1 d . . . H1 H 0.3479(12) 0.9519(12) 0.0835(4) 0.054(6) Uiso 1 1 d . . . H2 H 0.2951(13) 1.0324(13) 0.0842(5) 0.069(8) Uiso 1 1 d . . . H3 H 0.4741(13) 0.0768(14) 0.0837(5) 0.068(7) Uiso 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 0.0219(9) 0.0203(9) 0.0196(9) 0.0009(7) 0.0021(7) 0.0089(7) C2 0.0239(9) 0.0202(9) 0.0254(9) -0.0016(7) 0.0050(7) 0.0090(8) C3 0.0236(9) 0.0204(9) 0.0351(10) -0.0005(7) 0.0011(8) 0.0122(8) C4 0.0257(9) 0.0231(9) 0.0277(10) 0.0023(7) -0.0040(8) 0.0122(8) C5 0.0238(9) 0.0202(9) 0.0184(9) 0.0001(7) -0.0008(7) 0.0102(7) C6 0.0274(10) 0.0242(9) 0.0255(9) 0.0030(7) 0.0056(8) 0.0114(8) C7 0.0308(10) 0.0300(10) 0.0243(10) 0.0030(8) -0.0032(8) 0.0107(8) C8 0.0276(10) 0.0259(10) 0.0264(10) -0.0041(8) -0.0045(7) 0.0119(8) C9 0.0321(10) 0.0331(10) 0.0242(10) -0.0002(8) 0.0032(8) 0.0136(9) C10 0.0226(9) 0.0266(9) 0.0213(9) -0.0028(7) -0.0024(7) 0.0132(8) C11 0.0233(9) 0.0260(9) 0.0291(10) -0.0023(8) -0.0047(7) 0.0131(8) C12 0.0222(9) 0.0241(9) 0.0384(11) 0.0006(8) 0.0006(8) 0.0119(8) C13 0.0287(10) 0.0257(9) 0.0279(10) 0.0049(8) 0.0084(8) 0.0148(8) C14 0.0260(9) 0.0250(9) 0.0216(9) 0.0014(7) 0.0005(7) 0.0136(8) C15 0.0303(10) 0.0395(11) 0.0239(10) 0.0027(8) -0.0014(8) 0.0147(9) C16 0.0335(10) 0.0346(11) 0.0330(10) -0.0084(8) -0.0021(8) 0.0203(9) C17 0.0340(10) 0.0294(10) 0.0328(10) 0.0044(8) -0.0032(8) 0.0173(9) C18 0.0375(11) 0.0328(11) 0.0237(9) -0.0003(8) -0.0016(8) 0.0136(9) C19 0.0232(9) 0.0247(9) 0.0330(10) 0.0091(8) 0.0034(8) 0.0128(8) C20 0.0236(10) 0.0281(10) 0.0496(12) 0.0120(9) 0.0005(8) 0.0131(8) C21 0.0206(10) 0.0231(10) 0.0774(15) 0.0006(10) 0.0025(10) 0.0125(8) C22 0.0199(9) 0.0290(10) 0.0518(12) -0.0172(9) -0.0001(9) 0.0089(8) C23 0.0216(9) 0.0265(10) 0.0305(10) -0.0089(8) -0.0014(8) 0.0100(8) C24 0.0265(10) 0.0332(11) 0.0496(12) 0.0166(9) 0.0074(9) 0.0141(9) C25 0.0318(10) 0.0448(12) 0.0252(10) 0.0040(9) 0.0013(8) 0.0189(9) C26 0.0244(10) 0.0330(11) 0.0514(12) -0.0165(9) -0.0053(9) 0.0119(9) C27 0.0346(11) 0.0448(12) 0.0259(10) -0.0066(9) -0.0016(8) 0.0143(9) N1 0.0230(7) 0.0151(7) 0.0231(7) 0.0004(6) 0.0007(6) 0.0120(6) N2 0.0172(7) 0.0261(8) 0.0236(8) -0.0003(6) -0.0001(6) 0.0124(6) N3 0.0198(7) 0.0211(7) 0.0272(8) -0.0002(6) -0.0006(6) 0.0126(6) O1 0.0238(7) 0.0185(6) 0.0406(7) -0.0005(5) 0.0005(6) 0.0134(6) O2 0.0181(6) 0.0281(7) 0.0377(7) -0.0012(6) -0.0012(5) 0.0129(6) O3 0.0227(6) 0.0229(7) 0.0377(7) -0.0006(6) -0.0003(5) 0.0148(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N1 1.4884(19) . ? C1 C7 1.534(2) . ? C1 C2 1.536(2) . ? C1 C6 1.542(2) . ? C2 C3 1.520(2) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.520(2) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 C5 1.535(2) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 N1 1.4932(19) . ? C5 C9 1.529(2) . ? C5 C8 1.541(2) . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 N2 1.4935(19) . ? C10 C15 1.528(2) . ? C10 C11 1.536(2) . ? C10 C16 1.538(2) . ? C11 C12 1.521(2) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 C13 1.519(2) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 C14 1.538(2) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 N2 1.4957(19) . ? C14 C18 1.525(2) . ? C14 C17 1.536(2) . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C19 N3 1.494(2) . ? C19 C25 1.526(2) . ? C19 C20 1.534(2) . ? C19 C24 1.541(2) . ? C20 C21 1.517(2) . ? C20 H20A 0.9900 . ? C20 H20B 0.9900 . ? C21 C22 1.525(3) . ? C21 H21A 0.9900 . ? C21 H21B 0.9900 . ? C22 C23 1.536(2) . ? C22 H22A 0.9900 . ? C22 H22B 0.9900 . ? C23 N3 1.494(2) . ? C23 C27 1.530(2) . ? C23 C26 1.542(2) . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? C25 H25A 0.9800 . ? C25 H25B 0.9800 . ? C25 H25C 0.9800 . ? C26 H26A 0.9800 . ? C26 H26B 0.9800 . ? C26 H26C 0.9800 . ? C27 H27A 0.9800 . ? C27 H27B 0.9800 . ? C27 H27C 0.9800 . ? N1 O1 1.4503(16) . ? N2 O2 1.4653(16) . ? N3 O3 1.4602(15) . ? O1 H1 0.89(2) . ? O2 H2 0.89(2) . ? O3 H3 0.94(2) . ? 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 C1 C7 106.14(12) . . ? N1 C1 C2 106.37(12) . . ? C7 C1 C2 109.04(13) . . ? N1 C1 C6 115.89(13) . . ? C7 C1 C6 108.06(13) . . ? C2 C1 C6 111.08(13) . . ? C3 C2 C1 112.98(13) . . ? C3 C2 H2A 109.0 . . ? C1 C2 H2A 109.0 . . ? C3 C2 H2B 109.0 . . ? C1 C2 H2B 109.0 . . ? H2A C2 H2B 107.8 . . ? C2 C3 C4 109.08(13) . . ? C2 C3 H3A 109.9 . . ? C4 C3 H3A 109.9 . . ? C2 C3 H3B 109.9 . . ? C4 C3 H3B 109.9 . . ? H3A C3 H3B 108.3 . . ? C3 C4 C5 113.53(13) . . ? C3 C4 H4A 108.9 . . ? C5 C4 H4A 108.9 . . ? C3 C4 H4B 108.9 . . ? C5 C4 H4B 108.9 . . ? H4A C4 H4B 107.7 . . ? N1 C5 C9 106.39(12) . . ? N1 C5 C4 106.12(12) . . ? C9 C5 C4 108.83(13) . . ? N1 C5 C8 116.02(13) . . ? C9 C5 C8 108.30(13) . . ? C4 C5 C8 110.92(13) . . ? C1 C6 H6A 109.5 . . ? C1 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C1 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C1 C7 H7A 109.5 . . ? C1 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C1 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C5 C8 H8A 109.5 . . ? C5 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C5 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C5 C9 H9A 109.5 . . ? C5 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C5 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? N2 C10 C15 106.69(13) . . ? N2 C10 C11 105.96(12) . . ? C15 C10 C11 108.33(13) . . ? N2 C10 C16 116.16(13) . . ? C15 C10 C16 108.15(13) . . ? C11 C10 C16 111.24(13) . . ? C12 C11 C10 113.58(13) . . ? C12 C11 H11A 108.9 . . ? C10 C11 H11A 108.9 . . ? C12 C11 H11B 108.9 . . ? C10 C11 H11B 108.9 . . ? H11A C11 H11B 107.7 . . ? C13 C12 C11 109.27(13) . . ? C13 C12 H12A 109.8 . . ? C11 C12 H12A 109.8 . . ? C13 C12 H12B 109.8 . . ? C11 C12 H12B 109.8 . . ? H12A C12 H12B 108.3 . . ? C12 C13 C14 113.19(13) . . ? C12 C13 H13A 108.9 . . ? C14 C13 H13A 108.9 . . ? C12 C13 H13B 108.9 . . ? C14 C13 H13B 108.9 . . ? H13A C13 H13B 107.8 . . ? N2 C14 C18 106.86(13) . . ? N2 C14 C17 116.30(13) . . ? C18 C14 C17 107.80(13) . . ? N2 C14 C13 105.77(12) . . ? C18 C14 C13 108.61(13) . . ? C17 C14 C13 111.22(13) . . ? C10 C15 H15A 109.5 . . ? C10 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C10 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C10 C16 H16A 109.5 . . ? C10 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C10 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C14 C17 H17A 109.5 . . ? C14 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C14 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C14 C18 H18A 109.5 . . ? C14 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C14 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? N3 C19 C25 106.04(13) . . ? N3 C19 C20 106.14(13) . . ? C25 C19 C20 109.59(14) . . ? N3 C19 C24 115.48(14) . . ? C25 C19 C24 108.14(14) . . ? C20 C19 C24 111.24(13) . . ? C21 C20 C19 112.65(14) . . ? C21 C20 H20A 109.1 . . ? C19 C20 H20A 109.1 . . ? C21 C20 H20B 109.1 . . ? C19 C20 H20B 109.1 . . ? H20A C20 H20B 107.8 . . ? C20 C21 C22 109.80(14) . . ? C20 C21 H21A 109.7 . . ? C22 C21 H21A 109.7 . . ? C20 C21 H21B 109.7 . . ? C22 C21 H21B 109.7 . . ? H21A C21 H21B 108.2 . . ? C21 C22 C23 112.54(14) . . ? C21 C22 H22A 109.1 . . ? C23 C22 H22A 109.1 . . ? C21 C22 H22B 109.1 . . ? C23 C22 H22B 109.1 . . ? H22A C22 H22B 107.8 . . ? N3 C23 C27 106.05(13) . . ? N3 C23 C22 106.04(13) . . ? C27 C23 C22 109.55(14) . . ? N3 C23 C26 115.50(13) . . ? C27 C23 C26 108.10(14) . . ? C22 C23 C26 111.38(14) . . ? C19 C24 H24A 109.5 . . ? C19 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C19 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C19 C25 H25A 109.5 . . ? C19 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C19 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? C23 C26 H26A 109.5 . . ? C23 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C23 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C23 C27 H27A 109.5 . . ? C23 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C23 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? O1 N1 C1 107.44(11) . . ? O1 N1 C5 106.68(11) . . ? C1 N1 C5 119.71(12) . . ? O2 N2 C10 107.16(11) . . ? O2 N2 C14 107.36(11) . . ? C10 N2 C14 118.52(12) . . ? O3 N3 C19 106.67(11) . . ? O3 N3 C23 106.52(11) . . ? C19 N3 C23 118.29(12) . . ? N1 O1 H1 105.8(12) . . ? N2 O2 H2 106.0(13) . . ? N3 O3 H3 103.4(12) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1 H1 O2 0.89(2) 1.89(2) 2.7172(16) 152.1(17) . O2 H2 N3 0.89(2) 2.50(2) 3.2953(17) 149.0(18) 1_565 O3 H3 O1 0.94(2) 1.83(2) 2.7562(16) 169.2(19) 1_545 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.200 _refine_diff_density_min -0.199 _refine_diff_density_rms 0.036 #============================================================================== #============================================================================== data_unsaturatedIMes-TEMPO-H _database_code_depnum_ccdc_archive 'CCDC 793073' #TrackingRef 'CIF-final-combined.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C21 H24 N2, C9 H19 N O' _chemical_formula_sum 'C30 H43 N3 O' _chemical_formula_weight 461.67 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 Monoclinic _symmetry_space_group_name_H-M P2(1)/n _symmetry_space_group_name_Hall '-P 2yn ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 10.989(2) _cell_length_b 15.262(3) _cell_length_c 16.648(4) _cell_angle_alpha 90.00 _cell_angle_beta 94.250(3) _cell_angle_gamma 90.00 _cell_volume 2784.5(10) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 5971 _cell_measurement_theta_min 2.29 _cell_measurement_theta_max 28.24 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.232 _exptl_crystal_size_mid 0.189 _exptl_crystal_size_min 0.177 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.101 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1008 _exptl_absorpt_coefficient_mu 0.067 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6662 _exptl_absorpt_correction_T_max 0.7458 _exptl_absorpt_process_details '(SADABS; BRUKER 2009)' _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 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 22240 _diffrn_reflns_av_R_equivalents 0.0392 _diffrn_reflns_av_sigmaI/netI 0.0423 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.81 _diffrn_reflns_theta_max 28.77 _reflns_number_total 6707 _reflns_number_gt 4955 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _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^)+(0.0544P)^2^+0.8331P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6707 _refine_ls_number_parameters 311 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0695 _refine_ls_R_factor_gt 0.0475 _refine_ls_wR_factor_ref 0.1271 _refine_ls_wR_factor_gt 0.1140 _refine_ls_goodness_of_fit_ref 1.025 _refine_ls_restrained_S_all 1.025 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.02597(11) 0.64810(7) 0.10653(7) 0.0251(3) Uani 1 1 d . . . N2 N -0.01669(10) 0.78371(7) 0.09979(7) 0.0247(2) Uani 1 1 d . . . N3 N 0.48831(10) 0.23636(7) 0.12900(6) 0.0228(2) Uani 1 1 d . . . O1 O 0.39043(9) 0.24202(7) 0.18213(6) 0.0284(2) Uani 1 1 d . . . H1 H 0.4311(18) 0.2336(13) 0.2344(13) 0.058(6) Uiso 1 1 d . . . C1 C 0.01673(12) 0.71985(8) 0.15443(8) 0.0234(3) Uani 1 1 d . . . C2 C -0.00129(15) 0.66662(10) 0.02541(8) 0.0341(3) Uani 1 1 d . . . H2 H -0.0008 0.6266 -0.0183 0.041 Uiso 1 1 calc R . . C3 C -0.02842(15) 0.75219(9) 0.02119(8) 0.0334(3) Uani 1 1 d . . . H3 H -0.0512 0.7849 -0.0261 0.040 Uiso 1 1 calc R . . C4 C 0.05114(12) 0.56135(8) 0.13826(8) 0.0229(3) Uani 1 1 d . . . C5 C 0.16918(12) 0.53968(8) 0.16772(8) 0.0242(3) Uani 1 1 d . . . C6 C 0.18870(12) 0.45632(8) 0.20018(8) 0.0251(3) Uani 1 1 d . . . H6 H 0.2688 0.4403 0.2203 0.030 Uiso 1 1 calc R . . C7 C 0.09475(13) 0.39576(8) 0.20402(8) 0.0241(3) Uani 1 1 d . . . C8 C -0.02173(13) 0.42035(9) 0.17445(8) 0.0263(3) Uani 1 1 d . . . H8 H -0.0867 0.3797 0.1770 0.032 Uiso 1 1 calc R . . C9 C -0.04626(13) 0.50273(9) 0.14122(8) 0.0258(3) Uani 1 1 d . . . C10 C 0.27259(14) 0.60430(10) 0.16758(11) 0.0379(4) Uani 1 1 d . . . H10A H 0.2690 0.6444 0.2133 0.057 Uiso 1 1 calc R . . H10B H 0.2657 0.6379 0.1173 0.057 Uiso 1 1 calc R . . H10C H 0.3505 0.5728 0.1720 0.057 Uiso 1 1 calc R . . C11 C 0.12027(14) 0.30600(9) 0.23890(9) 0.0315(3) Uani 1 1 d . . . H11A H 0.2072 0.3011 0.2563 0.047 Uiso 0.50 1 calc PR . . H11B H 0.0986 0.2615 0.1979 0.047 Uiso 0.50 1 calc PR . . H11C H 0.0716 0.2971 0.2852 0.047 Uiso 0.50 1 calc PR . . H11D H 0.0444 0.2720 0.2366 0.047 Uiso 0.50 1 calc PR . . H11E H 0.1530 0.3116 0.2951 0.047 Uiso 0.50 1 calc PR . . H11F H 0.1800 0.2760 0.2077 0.047 Uiso 0.50 1 calc PR . . C12 C -0.17361(14) 0.52759(11) 0.11049(11) 0.0416(4) Uani 1 1 d . . . H12A H -0.1783 0.5310 0.0516 0.062 Uiso 1 1 calc R . . H12B H -0.1944 0.5847 0.1327 0.062 Uiso 1 1 calc R . . H12C H -0.2311 0.4833 0.1272 0.062 Uiso 1 1 calc R . . C13 C -0.04530(12) 0.87211(8) 0.12254(8) 0.0236(3) Uani 1 1 d . . . C14 C -0.15548(12) 0.88721(8) 0.15647(8) 0.0238(3) Uani 1 1 d . . . C15 C -0.18239(12) 0.97289(9) 0.17782(8) 0.0265(3) Uani 1 1 d . . . H15 H -0.2580 0.9846 0.1999 0.032 Uiso 1 1 calc R . . C16 C -0.10208(13) 1.04175(9) 0.16780(9) 0.0298(3) Uani 1 1 d . . . C17 C 0.00721(13) 1.02345(9) 0.13456(9) 0.0312(3) Uani 1 1 d . . . H17 H 0.0631 1.0699 0.1278 0.037 Uiso 1 1 calc R . . C18 C 0.03767(13) 0.93934(9) 0.11073(9) 0.0282(3) Uani 1 1 d . . . C19 C -0.24082(13) 0.81345(9) 0.17383(9) 0.0293(3) Uani 1 1 d . . . H19A H -0.2124 0.7850 0.2246 0.044 Uiso 1 1 calc R . . H19B H -0.2424 0.7705 0.1300 0.044 Uiso 1 1 calc R . . H19C H -0.3231 0.8368 0.1782 0.044 Uiso 1 1 calc R . . C20 C -0.13174(16) 1.13350(10) 0.19455(11) 0.0430(4) Uani 1 1 d . . . H20A H -0.0882 1.1455 0.2469 0.065 Uiso 1 1 calc R . . H20B H -0.2198 1.1386 0.1993 0.065 Uiso 1 1 calc R . . H20C H -0.1064 1.1758 0.1548 0.065 Uiso 1 1 calc R . . C21 C 0.15753(14) 0.92219(11) 0.07481(11) 0.0394(4) Uani 1 1 d . . . H21A H 0.1819 0.8611 0.0848 0.059 Uiso 1 1 calc R . . H21B H 0.2202 0.9613 0.0997 0.059 Uiso 1 1 calc R . . H21C H 0.1483 0.9330 0.0166 0.059 Uiso 1 1 calc R . . C22 C 0.47187(13) 0.15286(9) 0.08313(8) 0.0272(3) Uani 1 1 d . . . C23 C 0.57044(15) 0.14992(10) 0.02271(9) 0.0343(3) Uani 1 1 d . . . H23A H 0.6513 0.1439 0.0525 0.041 Uiso 1 1 calc R . . H23B H 0.5572 0.0976 -0.0120 0.041 Uiso 1 1 calc R . . C24 C 0.57084(16) 0.23120(10) -0.03030(9) 0.0361(4) Uani 1 1 d . . . H24A H 0.4930 0.2352 -0.0640 0.043 Uiso 1 1 calc R . . H24B H 0.6383 0.2275 -0.0664 0.043 Uiso 1 1 calc R . . C25 C 0.58707(14) 0.31198(10) 0.02313(9) 0.0323(3) Uani 1 1 d . . . H25A H 0.5847 0.3649 -0.0114 0.039 Uiso 1 1 calc R . . H25B H 0.6684 0.3095 0.0529 0.039 Uiso 1 1 calc R . . C26 C 0.48973(12) 0.32025(9) 0.08335(8) 0.0252(3) Uani 1 1 d . . . C27 C 0.34444(15) 0.13844(10) 0.04109(9) 0.0361(4) Uani 1 1 d . . . H27A H 0.2825 0.1501 0.0792 0.054 Uiso 1 1 calc R . . H27B H 0.3370 0.0777 0.0222 0.054 Uiso 1 1 calc R . . H27C H 0.3324 0.1783 -0.0050 0.054 Uiso 1 1 calc R . . C28 C 0.49590(15) 0.07883(10) 0.14469(9) 0.0337(3) Uani 1 1 d . . . H28A H 0.5716 0.0909 0.1777 0.051 Uiso 1 1 calc R . . H28B H 0.5037 0.0231 0.1163 0.051 Uiso 1 1 calc R . . H28C H 0.4278 0.0752 0.1794 0.051 Uiso 1 1 calc R . . C29 C 0.36661(14) 0.34841(10) 0.04114(9) 0.0336(3) Uani 1 1 d . . . H29A H 0.3484 0.3121 -0.0068 0.050 Uiso 1 1 calc R . . H29B H 0.3710 0.4101 0.0251 0.050 Uiso 1 1 calc R . . H29C H 0.3021 0.3411 0.0782 0.050 Uiso 1 1 calc R . . C30 C 0.52990(14) 0.39099(9) 0.14475(9) 0.0320(3) Uani 1 1 d . . . H30A H 0.4698 0.3956 0.1852 0.048 Uiso 1 1 calc R . . H30B H 0.5361 0.4474 0.1172 0.048 Uiso 1 1 calc R . . H30C H 0.6096 0.3754 0.1713 0.048 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0362(6) 0.0222(6) 0.0173(5) 0.0012(4) 0.0050(5) 0.0045(5) N2 0.0334(6) 0.0220(6) 0.0187(5) 0.0024(4) 0.0037(5) 0.0037(5) N3 0.0220(5) 0.0291(6) 0.0180(5) 0.0001(4) 0.0053(4) 0.0012(4) O1 0.0230(5) 0.0430(6) 0.0198(5) -0.0002(4) 0.0053(4) 0.0031(4) C1 0.0285(7) 0.0211(6) 0.0210(6) 0.0018(5) 0.0037(5) 0.0021(5) C2 0.0545(10) 0.0313(8) 0.0167(7) -0.0001(6) 0.0043(6) 0.0087(7) C3 0.0521(9) 0.0312(8) 0.0170(7) 0.0042(5) 0.0043(6) 0.0086(7) C4 0.0336(7) 0.0190(6) 0.0168(6) -0.0006(5) 0.0059(5) 0.0035(5) C5 0.0282(7) 0.0225(6) 0.0227(7) -0.0011(5) 0.0077(5) -0.0002(5) C6 0.0260(7) 0.0228(6) 0.0270(7) -0.0002(5) 0.0055(5) 0.0028(5) C7 0.0332(7) 0.0201(6) 0.0198(6) -0.0011(5) 0.0070(5) 0.0014(5) C8 0.0306(7) 0.0250(7) 0.0236(7) -0.0030(5) 0.0040(6) -0.0050(5) C9 0.0305(7) 0.0259(7) 0.0209(7) -0.0033(5) 0.0005(5) 0.0007(5) C10 0.0323(8) 0.0268(7) 0.0558(10) 0.0069(7) 0.0101(7) -0.0028(6) C11 0.0383(8) 0.0227(7) 0.0340(8) 0.0039(6) 0.0062(6) 0.0006(6) C12 0.0340(8) 0.0404(9) 0.0487(10) 0.0058(8) -0.0078(7) 0.0011(7) C13 0.0301(7) 0.0209(6) 0.0197(6) 0.0029(5) 0.0002(5) 0.0036(5) C14 0.0284(7) 0.0232(6) 0.0195(6) 0.0015(5) -0.0015(5) -0.0001(5) C15 0.0266(7) 0.0268(7) 0.0258(7) -0.0006(5) -0.0002(5) 0.0031(5) C16 0.0348(8) 0.0229(7) 0.0309(8) 0.0001(5) -0.0032(6) 0.0008(6) C17 0.0324(7) 0.0244(7) 0.0364(8) 0.0062(6) 0.0002(6) -0.0043(6) C18 0.0287(7) 0.0274(7) 0.0284(7) 0.0069(6) 0.0016(6) 0.0013(5) C19 0.0333(7) 0.0271(7) 0.0277(7) -0.0026(6) 0.0037(6) -0.0044(6) C20 0.0482(10) 0.0251(8) 0.0554(11) -0.0062(7) 0.0010(8) 0.0014(7) C21 0.0338(8) 0.0395(9) 0.0459(10) 0.0065(7) 0.0100(7) 0.0014(7) C22 0.0329(7) 0.0277(7) 0.0215(7) 0.0002(5) 0.0056(6) -0.0024(6) C23 0.0452(9) 0.0321(8) 0.0273(8) -0.0031(6) 0.0136(7) -0.0001(6) C24 0.0470(9) 0.0381(8) 0.0250(7) 0.0006(6) 0.0150(7) -0.0031(7) C25 0.0385(8) 0.0311(8) 0.0281(7) 0.0035(6) 0.0081(6) -0.0044(6) C26 0.0273(7) 0.0276(7) 0.0203(6) 0.0008(5) 0.0000(5) 0.0004(5) C27 0.0435(9) 0.0371(8) 0.0271(8) 0.0012(6) -0.0018(7) -0.0116(7) C28 0.0430(9) 0.0301(8) 0.0289(8) 0.0038(6) 0.0080(6) 0.0003(6) C29 0.0367(8) 0.0336(8) 0.0294(8) 0.0019(6) -0.0058(6) 0.0041(6) C30 0.0352(8) 0.0309(8) 0.0294(8) -0.0031(6) -0.0023(6) -0.0002(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C1 1.3629(17) . ? N1 C2 1.3905(18) . ? N1 C4 1.4446(16) . ? N2 C1 1.3648(16) . ? N2 C3 1.3913(18) . ? N2 C13 1.4422(17) . ? N3 O1 1.4448(14) . ? N3 C26 1.4895(17) . ? N3 C22 1.4898(17) . ? O1 H1 0.96(2) . ? C2 C3 1.340(2) . ? C2 H2 0.9500 . ? C3 H3 0.9500 . ? C4 C5 1.3923(19) . ? C4 C9 1.3987(19) . ? C5 C6 1.3926(18) . ? C5 C10 1.5048(19) . ? C6 C7 1.3908(19) . ? C6 H6 0.9500 . ? C7 C8 1.389(2) . ? C7 C11 1.5060(18) . ? C8 C9 1.3919(19) . ? C8 H8 0.9500 . ? C9 C12 1.503(2) . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C11 H11D 0.9800 . ? C11 H11E 0.9800 . ? C11 H11F 0.9800 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 C14 1.3926(19) . ? C13 C18 1.3963(19) . ? C14 C15 1.3925(19) . ? C14 C19 1.5068(19) . ? C15 C16 1.390(2) . ? C15 H15 0.9500 . ? C16 C17 1.388(2) . ? C16 C20 1.512(2) . ? C17 C18 1.392(2) . ? C17 H17 0.9500 . ? C18 C21 1.509(2) . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? C22 C23 1.532(2) . ? C22 C27 1.534(2) . ? C22 C28 1.5351(19) . ? C23 C24 1.523(2) . ? C23 H23A 0.9900 . ? C23 H23B 0.9900 . ? C24 C25 1.523(2) . ? C24 H24A 0.9900 . ? C24 H24B 0.9900 . ? C25 C26 1.524(2) . ? C25 H25A 0.9900 . ? C25 H25B 0.9900 . ? C26 C30 1.5293(19) . ? C26 C29 1.5388(19) . ? C27 H27A 0.9800 . ? C27 H27B 0.9800 . ? C27 H27C 0.9800 . ? C28 H28A 0.9800 . ? C28 H28B 0.9800 . ? C28 H28C 0.9800 . ? C29 H29A 0.9800 . ? C29 H29B 0.9800 . ? C29 H29C 0.9800 . ? C30 H30A 0.9800 . ? C30 H30B 0.9800 . ? C30 H30C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 N1 C2 112.64(11) . . ? C1 N1 C4 122.89(11) . . ? C2 N1 C4 124.27(11) . . ? C1 N2 C3 112.43(11) . . ? C1 N2 C13 123.10(11) . . ? C3 N2 C13 124.31(11) . . ? O1 N3 C26 107.30(10) . . ? O1 N3 C22 107.30(10) . . ? C26 N3 C22 118.62(10) . . ? N3 O1 H1 103.3(12) . . ? N1 C1 N2 102.23(11) . . ? C3 C2 N1 106.27(12) . . ? C3 C2 H2 126.9 . . ? N1 C2 H2 126.9 . . ? C2 C3 N2 106.43(12) . . ? C2 C3 H3 126.8 . . ? N2 C3 H3 126.8 . . ? C5 C4 C9 122.08(12) . . ? C5 C4 N1 119.65(12) . . ? C9 C4 N1 118.22(12) . . ? C4 C5 C6 117.80(12) . . ? C4 C5 C10 121.85(12) . . ? C6 C5 C10 120.32(12) . . ? C7 C6 C5 122.11(12) . . ? C7 C6 H6 118.9 . . ? C5 C6 H6 118.9 . . ? C8 C7 C6 118.16(12) . . ? C8 C7 C11 121.53(12) . . ? C6 C7 C11 120.30(12) . . ? C7 C8 C9 122.10(13) . . ? C7 C8 H8 119.0 . . ? C9 C8 H8 119.0 . . ? C8 C9 C4 117.75(12) . . ? C8 C9 C12 120.76(13) . . ? C4 C9 C12 121.49(13) . . ? C5 C10 H10A 109.5 . . ? C5 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C5 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C7 C11 H11A 109.5 . . ? C7 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C7 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C7 C11 H11D 109.5 . . ? H11A C11 H11D 141.1 . . ? H11B C11 H11D 56.3 . . ? H11C C11 H11D 56.3 . . ? C7 C11 H11E 109.5 . . ? H11A C11 H11E 56.3 . . ? H11B C11 H11E 141.1 . . ? H11C C11 H11E 56.3 . . ? H11D C11 H11E 109.5 . . ? C7 C11 H11F 109.5 . . ? H11A C11 H11F 56.3 . . ? H11B C11 H11F 56.3 . . ? H11C C11 H11F 141.1 . . ? H11D C11 H11F 109.5 . . ? H11E C11 H11F 109.5 . . ? C9 C12 H12A 109.5 . . ? C9 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C9 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C14 C13 C18 122.14(12) . . ? C14 C13 N2 118.31(12) . . ? C18 C13 N2 119.55(12) . . ? C15 C14 C13 117.80(12) . . ? C15 C14 C19 120.37(13) . . ? C13 C14 C19 121.76(12) . . ? C16 C15 C14 122.04(13) . . ? C16 C15 H15 119.0 . . ? C14 C15 H15 119.0 . . ? C17 C16 C15 118.14(13) . . ? C17 C16 C20 121.04(13) . . ? C15 C16 C20 120.80(14) . . ? C16 C17 C18 122.20(13) . . ? C16 C17 H17 118.9 . . ? C18 C17 H17 118.9 . . ? C17 C18 C13 117.67(13) . . ? C17 C18 C21 120.56(13) . . ? C13 C18 C21 121.77(13) . . ? C14 C19 H19A 109.5 . . ? C14 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C14 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C16 C20 H20A 109.5 . . ? C16 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C16 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C18 C21 H21A 109.5 . . ? C18 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C18 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? N3 C22 C23 107.26(11) . . ? N3 C22 C27 115.37(12) . . ? C23 C22 C27 111.23(12) . . ? N3 C22 C28 106.20(11) . . ? C23 C22 C28 108.76(12) . . ? C27 C22 C28 107.76(12) . . ? C24 C23 C22 112.89(13) . . ? C24 C23 H23A 109.0 . . ? C22 C23 H23A 109.0 . . ? C24 C23 H23B 109.0 . . ? C22 C23 H23B 109.0 . . ? H23A C23 H23B 107.8 . . ? C23 C24 C25 109.04(12) . . ? C23 C24 H24A 109.9 . . ? C25 C24 H24A 109.9 . . ? C23 C24 H24B 109.9 . . ? C25 C24 H24B 109.9 . . ? H24A C24 H24B 108.3 . . ? C24 C25 C26 113.17(12) . . ? C24 C25 H25A 108.9 . . ? C26 C25 H25A 108.9 . . ? C24 C25 H25B 108.9 . . ? C26 C25 H25B 108.9 . . ? H25A C25 H25B 107.8 . . ? N3 C26 C25 107.39(11) . . ? N3 C26 C30 106.21(11) . . ? C25 C26 C30 108.42(12) . . ? N3 C26 C29 115.53(11) . . ? C25 C26 C29 111.04(12) . . ? C30 C26 C29 107.97(11) . . ? C22 C27 H27A 109.5 . . ? C22 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C22 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? C22 C28 H28A 109.5 . . ? C22 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C22 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? C26 C29 H29A 109.5 . . ? C26 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? C26 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? C26 C30 H30A 109.5 . . ? C26 C30 H30B 109.5 . . ? H30A C30 H30B 109.5 . . ? C26 C30 H30C 109.5 . . ? H30A C30 H30C 109.5 . . ? H30B C30 H30C 109.5 . . ? 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 C2 N1 C1 N2 -0.32(16) . . . . ? C4 N1 C1 N2 -175.34(12) . . . . ? C3 N2 C1 N1 0.42(15) . . . . ? C13 N2 C1 N1 176.03(12) . . . . ? C1 N1 C2 C3 0.10(18) . . . . ? C4 N1 C2 C3 175.04(13) . . . . ? N1 C2 C3 N2 0.16(18) . . . . ? C1 N2 C3 C2 -0.38(18) . . . . ? C13 N2 C3 C2 -175.92(13) . . . . ? C1 N1 C4 C5 -76.04(17) . . . . ? C2 N1 C4 C5 109.52(16) . . . . ? C1 N1 C4 C9 101.39(15) . . . . ? C2 N1 C4 C9 -73.05(18) . . . . ? C9 C4 C5 C6 0.60(19) . . . . ? N1 C4 C5 C6 177.94(12) . . . . ? C9 C4 C5 C10 -177.37(13) . . . . ? N1 C4 C5 C10 0.0(2) . . . . ? C4 C5 C6 C7 -0.3(2) . . . . ? C10 C5 C6 C7 177.72(13) . . . . ? C5 C6 C7 C8 -0.2(2) . . . . ? C5 C6 C7 C11 179.40(13) . . . . ? C6 C7 C8 C9 0.3(2) . . . . ? C11 C7 C8 C9 -179.24(13) . . . . ? C7 C8 C9 C4 0.0(2) . . . . ? C7 C8 C9 C12 -179.40(14) . . . . ? C5 C4 C9 C8 -0.5(2) . . . . ? N1 C4 C9 C8 -177.83(12) . . . . ? C5 C4 C9 C12 178.92(14) . . . . ? N1 C4 C9 C12 1.55(19) . . . . ? C1 N2 C13 C14 -73.29(17) . . . . ? C3 N2 C13 C14 101.79(16) . . . . ? C1 N2 C13 C18 106.18(15) . . . . ? C3 N2 C13 C18 -78.74(18) . . . . ? C18 C13 C14 C15 0.85(19) . . . . ? N2 C13 C14 C15 -179.68(11) . . . . ? C18 C13 C14 C19 -176.06(12) . . . . ? N2 C13 C14 C19 3.40(18) . . . . ? C13 C14 C15 C16 -1.4(2) . . . . ? C19 C14 C15 C16 175.55(13) . . . . ? C14 C15 C16 C17 0.7(2) . . . . ? C14 C15 C16 C20 -177.60(13) . . . . ? C15 C16 C17 C18 0.5(2) . . . . ? C20 C16 C17 C18 178.87(14) . . . . ? C16 C17 C18 C13 -1.0(2) . . . . ? C16 C17 C18 C21 180.00(14) . . . . ? C14 C13 C18 C17 0.3(2) . . . . ? N2 C13 C18 C17 -179.13(12) . . . . ? C14 C13 C18 C21 179.27(13) . . . . ? N2 C13 C18 C21 -0.2(2) . . . . ? O1 N3 C22 C23 176.18(10) . . . . ? C26 N3 C22 C23 54.52(15) . . . . ? O1 N3 C22 C27 51.64(14) . . . . ? C26 N3 C22 C27 -70.02(15) . . . . ? O1 N3 C22 C28 -67.65(12) . . . . ? C26 N3 C22 C28 170.69(11) . . . . ? N3 C22 C23 C24 -53.71(16) . . . . ? C27 C22 C23 C24 73.31(16) . . . . ? C28 C22 C23 C24 -168.17(13) . . . . ? C22 C23 C24 C25 56.86(17) . . . . ? C23 C24 C25 C26 -56.92(17) . . . . ? O1 N3 C26 C25 -176.14(10) . . . . ? C22 N3 C26 C25 -54.48(14) . . . . ? O1 N3 C26 C30 68.02(12) . . . . ? C22 N3 C26 C30 -170.32(11) . . . . ? O1 N3 C26 C29 -51.64(14) . . . . ? C22 N3 C26 C29 70.02(15) . . . . ? C24 C25 C26 N3 53.61(15) . . . . ? C24 C25 C26 C30 167.98(12) . . . . ? C24 C25 C26 C29 -73.57(16) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1 H1 C1 0.96(2) 1.91(2) 2.8543(17) 169.6(18) 2_545 O1 H1 N1 0.96(2) 2.96(2) 3.8469(17) 155.0(15) 2_545 O1 H1 N2 0.96(2) 2.95(2) 3.8424(16) 155.6(15) 2_545 _diffrn_measured_fraction_theta_max 0.926 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.273 _refine_diff_density_min -0.247 _refine_diff_density_rms 0.040 #============================================================================== #============================================================================== data_Ph3PC(H)C(=O)ON(C5H6(CH3)4) _database_code_depnum_ccdc_archive 'CCDC 793074' #TrackingRef 'CIF-final-combined.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C29 H34 N O2 P' _chemical_formula_sum 'C29 H34 N O2 P' _chemical_formula_weight 459.54 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 11.9030(13) _cell_length_b 12.1631(13) _cell_length_c 18.100(2) _cell_angle_alpha 90.00 _cell_angle_beta 93.6420(10) _cell_angle_gamma 90.00 _cell_volume 2615.1(5) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 6845 _cell_measurement_theta_min 2.26 _cell_measurement_theta_max 27.98 _exptl_crystal_description rectangle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.4021 _exptl_crystal_size_mid 0.3726 _exptl_crystal_size_min 0.2189 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.167 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 984 _exptl_absorpt_coefficient_mu 0.130 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6680 _exptl_absorpt_correction_T_max 0.7457 _exptl_absorpt_process_details 'SADABS; Bruker 2009' _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 20480 _diffrn_reflns_av_R_equivalents 0.0492 _diffrn_reflns_av_sigmaI/netI 0.0500 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.02 _diffrn_reflns_theta_max 28.69 _reflns_number_total 6326 _reflns_number_gt 4972 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _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^)+(0.0478P)^2^+1.1752P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6326 _refine_ls_number_parameters 302 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0591 _refine_ls_R_factor_gt 0.0419 _refine_ls_wR_factor_ref 0.1133 _refine_ls_wR_factor_gt 0.1017 _refine_ls_goodness_of_fit_ref 1.020 _refine_ls_restrained_S_all 1.020 _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 P1 P 0.76095(3) 0.21697(3) 0.085894(19) 0.01480(10) Uani 1 1 d . . . N1 N 0.39892(10) 0.29952(10) 0.10052(6) 0.0173(2) Uani 1 1 d . . . O1 O 0.46033(8) 0.25230(8) 0.16507(5) 0.0166(2) Uani 1 1 d . . . O2 O 0.62504(8) 0.20487(8) 0.21578(5) 0.0194(2) Uani 1 1 d . . . C1 C 0.81447(12) 0.08036(12) 0.10546(8) 0.0175(3) Uani 1 1 d . . . C2 C 0.74981(13) 0.00679(12) 0.14367(8) 0.0221(3) Uani 1 1 d . . . H2 H 0.6766 0.0252 0.1540 0.026 Uiso 1 1 calc R . . C3 C 0.79430(14) -0.09393(13) 0.16642(9) 0.0251(3) Uani 1 1 d . . . H3 H 0.7514 -0.1424 0.1927 0.030 Uiso 1 1 calc R . . C4 C 0.90272(14) -0.12248(13) 0.14999(8) 0.0253(3) Uani 1 1 d . . . H4 H 0.9331 -0.1893 0.1663 0.030 Uiso 1 1 calc R . . C5 C 0.96598(13) -0.05149(13) 0.10916(9) 0.0259(3) Uani 1 1 d . . . H5 H 1.0376 -0.0720 0.0967 0.031 Uiso 1 1 calc R . . C6 C 0.92246(13) 0.04998(13) 0.08698(8) 0.0227(3) Uani 1 1 d . . . H6 H 0.9650 0.0977 0.0599 0.027 Uiso 1 1 calc R . . C7 C 0.80223(12) 0.25074(11) -0.00584(7) 0.0160(3) Uani 1 1 d . . . C8 C 0.73848(12) 0.21096(13) -0.06762(8) 0.0217(3) Uani 1 1 d . . . H8 H 0.6751 0.1681 -0.0614 0.026 Uiso 1 1 calc R . . C9 C 0.77007(13) 0.23564(14) -0.13843(8) 0.0263(3) Uani 1 1 d . . . H9 H 0.7275 0.2091 -0.1795 0.032 Uiso 1 1 calc R . . C10 C 0.86458(13) 0.29957(13) -0.14832(8) 0.0239(3) Uani 1 1 d . . . H10 H 0.8850 0.3162 -0.1958 0.029 Uiso 1 1 calc R . . C11 C 0.92812(12) 0.33840(12) -0.08744(8) 0.0210(3) Uani 1 1 d . . . H11 H 0.9916 0.3811 -0.0940 0.025 Uiso 1 1 calc R . . C12 C 0.89774(12) 0.31402(12) -0.01617(8) 0.0186(3) Uani 1 1 d . . . H12 H 0.9412 0.3400 0.0246 0.022 Uiso 1 1 calc R . . C13 C 0.84120(12) 0.30757(12) 0.14844(8) 0.0196(3) Uani 1 1 d . . . C14 C 0.92596(13) 0.27201(16) 0.19843(9) 0.0306(4) Uani 1 1 d . . . H14 H 0.9431 0.1976 0.2025 0.037 Uiso 1 1 calc R . . C15 C 0.98569(14) 0.34892(19) 0.24282(11) 0.0412(5) Uani 1 1 d . . . H15 H 1.0428 0.3255 0.2766 0.049 Uiso 1 1 calc R . . C16 C 0.96049(15) 0.45952(17) 0.23678(10) 0.0387(5) Uani 1 1 d . . . H16 H 1.0020 0.5103 0.2657 0.046 Uiso 1 1 calc R . . C17 C 0.87443(15) 0.49511(15) 0.18834(9) 0.0321(4) Uani 1 1 d . . . H17 H 0.8565 0.5695 0.1853 0.039 Uiso 1 1 calc R . . C18 C 0.81483(14) 0.41979(13) 0.14425(8) 0.0252(3) Uani 1 1 d . . . H18 H 0.7566 0.4438 0.1115 0.030 Uiso 1 1 calc R . . C19 C 0.61893(12) 0.23572(12) 0.08722(8) 0.0173(3) Uani 1 1 d . . . H19 H 0.5765(15) 0.2583(15) 0.0425(10) 0.028(5) Uiso 1 1 d . . . C20 C 0.57387(11) 0.23035(11) 0.15700(8) 0.0160(3) Uani 1 1 d . . . C21 C 0.37304(12) 0.41562(12) 0.12057(8) 0.0191(3) Uani 1 1 d . . . C22 C 0.30070(13) 0.46325(13) 0.05530(9) 0.0253(3) Uani 1 1 d . . . H22A H 0.2775 0.5371 0.0677 0.030 Uiso 1 1 calc R . . H22B H 0.3458 0.4683 0.0126 0.030 Uiso 1 1 calc R . . C23 C 0.19673(14) 0.39445(15) 0.03509(9) 0.0303(4) Uani 1 1 d . . . H23A H 0.1546 0.4267 -0.0071 0.036 Uiso 1 1 calc R . . H23B H 0.1485 0.3927 0.0763 0.036 Uiso 1 1 calc R . . C24 C 0.23278(14) 0.27829(15) 0.01642(9) 0.0289(4) Uani 1 1 d . . . H24A H 0.2758 0.2807 -0.0273 0.035 Uiso 1 1 calc R . . H24B H 0.1661 0.2342 0.0047 0.035 Uiso 1 1 calc R . . C25 C 0.30425(13) 0.22244(13) 0.07972(8) 0.0226(3) Uani 1 1 d . . . C26 C 0.48511(13) 0.47787(13) 0.12693(9) 0.0245(3) Uani 1 1 d . . . H26A H 0.5297 0.4521 0.1695 0.037 Uiso 1 1 calc R . . H26B H 0.4709 0.5551 0.1321 0.037 Uiso 1 1 calc R . . H26C H 0.5249 0.4654 0.0832 0.037 Uiso 1 1 calc R . . C27 C 0.31586(13) 0.43159(13) 0.19389(8) 0.0243(3) Uani 1 1 d . . . H27A H 0.2391 0.4072 0.1879 0.037 Uiso 1 1 calc R . . H27B H 0.3177 0.5080 0.2072 0.037 Uiso 1 1 calc R . . H27C H 0.3552 0.3895 0.2322 0.037 Uiso 1 1 calc R . . C28 C 0.35647(15) 0.11817(14) 0.04955(10) 0.0312(4) Uani 1 1 d . . . H28A H 0.4033 0.1372 0.0102 0.047 Uiso 1 1 calc R . . H28B H 0.2978 0.0695 0.0310 0.047 Uiso 1 1 calc R . . H28C H 0.4011 0.0823 0.0885 0.047 Uiso 1 1 calc R . . C29 C 0.23049(14) 0.18906(15) 0.14288(9) 0.0287(4) Uani 1 1 d . . . H29A H 0.2778 0.1665 0.1851 0.043 Uiso 1 1 calc R . . H29B H 0.1822 0.1293 0.1268 0.043 Uiso 1 1 calc R . . H29C H 0.1854 0.2506 0.1561 0.043 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 P1 0.01359(17) 0.01568(18) 0.01543(17) 0.00040(13) 0.00319(13) 0.00153(13) N1 0.0143(6) 0.0208(6) 0.0165(6) 0.0033(5) -0.0009(4) 0.0022(5) O1 0.0134(5) 0.0210(5) 0.0154(5) 0.0034(4) 0.0023(4) 0.0030(4) O2 0.0194(5) 0.0205(5) 0.0182(5) 0.0006(4) 0.0004(4) 0.0044(4) C1 0.0187(7) 0.0173(7) 0.0169(6) 0.0010(5) 0.0037(5) 0.0040(5) C2 0.0230(8) 0.0203(7) 0.0240(7) 0.0009(6) 0.0095(6) 0.0044(6) C3 0.0313(8) 0.0207(8) 0.0248(8) 0.0041(6) 0.0132(6) 0.0041(6) C4 0.0328(9) 0.0195(7) 0.0244(8) 0.0034(6) 0.0073(7) 0.0102(6) C5 0.0227(8) 0.0270(8) 0.0287(8) 0.0035(6) 0.0081(6) 0.0100(6) C6 0.0214(7) 0.0221(7) 0.0252(8) 0.0037(6) 0.0066(6) 0.0037(6) C7 0.0152(6) 0.0167(6) 0.0164(6) 0.0008(5) 0.0039(5) 0.0046(5) C8 0.0162(7) 0.0270(8) 0.0222(7) -0.0026(6) 0.0032(6) -0.0001(6) C9 0.0207(8) 0.0404(10) 0.0176(7) -0.0041(6) -0.0001(6) 0.0021(7) C10 0.0230(8) 0.0318(9) 0.0177(7) 0.0045(6) 0.0062(6) 0.0081(6) C11 0.0181(7) 0.0228(7) 0.0227(7) 0.0033(6) 0.0061(6) 0.0014(6) C12 0.0169(7) 0.0205(7) 0.0183(7) -0.0002(5) 0.0016(5) 0.0019(5) C13 0.0169(7) 0.0244(7) 0.0181(7) -0.0031(6) 0.0062(5) -0.0017(6) C14 0.0192(8) 0.0425(10) 0.0299(8) -0.0101(7) -0.0002(6) 0.0073(7) C15 0.0173(8) 0.0700(14) 0.0358(10) -0.0198(9) -0.0022(7) 0.0038(8) C16 0.0254(9) 0.0549(12) 0.0376(10) -0.0250(9) 0.0162(8) -0.0184(8) C17 0.0407(10) 0.0298(9) 0.0279(8) -0.0083(7) 0.0179(8) -0.0140(7) C18 0.0320(8) 0.0244(8) 0.0199(7) -0.0013(6) 0.0079(6) -0.0044(7) C19 0.0138(7) 0.0209(7) 0.0173(7) 0.0012(5) 0.0024(5) 0.0024(5) C20 0.0150(7) 0.0127(6) 0.0205(7) -0.0005(5) 0.0024(5) 0.0017(5) C21 0.0168(7) 0.0201(7) 0.0206(7) 0.0035(5) 0.0041(6) 0.0038(5) C22 0.0219(8) 0.0280(8) 0.0263(8) 0.0081(6) 0.0029(6) 0.0066(6) C23 0.0215(8) 0.0406(10) 0.0280(8) 0.0087(7) -0.0041(6) 0.0050(7) C24 0.0225(8) 0.0400(10) 0.0236(8) 0.0000(7) -0.0041(6) -0.0017(7) C25 0.0181(7) 0.0269(8) 0.0224(7) -0.0003(6) -0.0008(6) -0.0025(6) C26 0.0225(8) 0.0194(7) 0.0320(8) 0.0022(6) 0.0050(6) 0.0000(6) C27 0.0229(8) 0.0270(8) 0.0239(8) -0.0007(6) 0.0071(6) 0.0053(6) C28 0.0293(9) 0.0282(9) 0.0356(9) -0.0081(7) -0.0011(7) -0.0043(7) C29 0.0205(8) 0.0338(9) 0.0320(9) 0.0041(7) 0.0027(7) -0.0071(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag P1 C19 1.7075(14) . ? P1 C1 1.8065(15) . ? P1 C7 1.8085(14) . ? P1 C13 1.8086(15) . ? N1 O1 1.4562(15) . ? N1 C21 1.4950(19) . ? N1 C25 1.4955(19) . ? O1 C20 1.3944(16) . ? O2 C20 1.2315(17) . ? C1 C2 1.392(2) . ? C1 C6 1.3983(19) . ? C2 C3 1.387(2) . ? C2 H2 0.9300 . ? C3 C4 1.387(2) . ? C3 H3 0.9300 . ? C4 C5 1.389(2) . ? C4 H4 0.9300 . ? C5 C6 1.388(2) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C7 C12 1.395(2) . ? C7 C8 1.397(2) . ? C8 C9 1.391(2) . ? C8 H8 0.9300 . ? C9 C10 1.388(2) . ? C9 H9 0.9300 . ? C10 C11 1.380(2) . ? C10 H10 0.9300 . ? C11 C12 1.3936(19) . ? C11 H11 0.9300 . ? C12 H12 0.9300 . ? C13 C14 1.381(2) . ? C13 C18 1.401(2) . ? C14 C15 1.398(3) . ? C14 H14 0.9300 . ? C15 C16 1.381(3) . ? C15 H15 0.9300 . ? C16 C17 1.375(3) . ? C16 H16 0.9300 . ? C17 C18 1.381(2) . ? C17 H17 0.9300 . ? C18 H18 0.9300 . ? C19 C20 1.4046(19) . ? C19 H19 0.966(18) . ? C21 C22 1.531(2) . ? C21 C26 1.532(2) . ? C21 C27 1.5416(19) . ? C22 C23 1.519(2) . ? C22 H22A 0.9700 . ? C22 H22B 0.9700 . ? C23 C24 1.521(2) . ? C23 H23A 0.9700 . ? C23 H23B 0.9700 . ? C24 C25 1.541(2) . ? C24 H24A 0.9700 . ? C24 H24B 0.9700 . ? C25 C28 1.528(2) . ? C25 C29 1.540(2) . ? C26 H26A 0.9600 . ? C26 H26B 0.9600 . ? C26 H26C 0.9600 . ? C27 H27A 0.9600 . ? C27 H27B 0.9600 . ? C27 H27C 0.9600 . ? C28 H28A 0.9600 . ? C28 H28B 0.9600 . ? C28 H28C 0.9600 . ? C29 H29A 0.9600 . ? C29 H29B 0.9600 . ? C29 H29C 0.9600 . ? 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 C19 P1 C1 117.21(7) . . ? C19 P1 C7 108.03(7) . . ? C1 P1 C7 106.02(6) . . ? C19 P1 C13 113.19(7) . . ? C1 P1 C13 105.79(7) . . ? C7 P1 C13 105.83(7) . . ? O1 N1 C21 106.17(10) . . ? O1 N1 C25 106.65(10) . . ? C21 N1 C25 119.32(11) . . ? C20 O1 N1 115.58(9) . . ? C2 C1 C6 119.63(13) . . ? C2 C1 P1 119.30(10) . . ? C6 C1 P1 120.94(11) . . ? C3 C2 C1 120.17(13) . . ? C3 C2 H2 119.9 . . ? C1 C2 H2 119.9 . . ? C2 C3 C4 120.03(14) . . ? C2 C3 H3 120.0 . . ? C4 C3 H3 120.0 . . ? C3 C4 C5 120.11(14) . . ? C3 C4 H4 119.9 . . ? C5 C4 H4 119.9 . . ? C6 C5 C4 120.11(14) . . ? C6 C5 H5 119.9 . . ? C4 C5 H5 119.9 . . ? C5 C6 C1 119.85(14) . . ? C5 C6 H6 120.1 . . ? C1 C6 H6 120.1 . . ? C12 C7 C8 119.31(12) . . ? C12 C7 P1 121.30(11) . . ? C8 C7 P1 119.38(11) . . ? C9 C8 C7 119.85(14) . . ? C9 C8 H8 120.1 . . ? C7 C8 H8 120.1 . . ? C10 C9 C8 120.55(15) . . ? C10 C9 H9 119.7 . . ? C8 C9 H9 119.7 . . ? C11 C10 C9 119.75(13) . . ? C11 C10 H10 120.1 . . ? C9 C10 H10 120.1 . . ? C10 C11 C12 120.34(14) . . ? C10 C11 H11 119.8 . . ? C12 C11 H11 119.8 . . ? C11 C12 C7 120.20(14) . . ? C11 C12 H12 119.9 . . ? C7 C12 H12 119.9 . . ? C14 C13 C18 119.48(15) . . ? C14 C13 P1 123.64(12) . . ? C18 C13 P1 116.87(12) . . ? C13 C14 C15 119.39(17) . . ? C13 C14 H14 120.3 . . ? C15 C14 H14 120.3 . . ? C16 C15 C14 120.42(18) . . ? C16 C15 H15 119.8 . . ? C14 C15 H15 119.8 . . ? C17 C16 C15 120.42(17) . . ? C17 C16 H16 119.8 . . ? C15 C16 H16 119.8 . . ? C16 C17 C18 119.61(17) . . ? C16 C17 H17 120.2 . . ? C18 C17 H17 120.2 . . ? C17 C18 C13 120.65(16) . . ? C17 C18 H18 119.7 . . ? C13 C18 H18 119.7 . . ? C20 C19 P1 116.19(11) . . ? C20 C19 H19 123.8(11) . . ? P1 C19 H19 119.5(10) . . ? O2 C20 O1 112.77(11) . . ? O2 C20 C19 126.32(13) . . ? O1 C20 C19 120.89(13) . . ? N1 C21 C22 106.53(12) . . ? N1 C21 C26 107.05(11) . . ? C22 C21 C26 108.38(12) . . ? N1 C21 C27 115.91(12) . . ? C22 C21 C27 111.04(12) . . ? C26 C21 C27 107.64(13) . . ? C23 C22 C21 112.78(13) . . ? C23 C22 H22A 109.0 . . ? C21 C22 H22A 109.0 . . ? C23 C22 H22B 109.0 . . ? C21 C22 H22B 109.0 . . ? H22A C22 H22B 107.8 . . ? C22 C23 C24 109.16(13) . . ? C22 C23 H23A 109.8 . . ? C24 C23 H23A 109.8 . . ? C22 C23 H23B 109.8 . . ? C24 C23 H23B 109.8 . . ? H23A C23 H23B 108.3 . . ? C23 C24 C25 113.24(13) . . ? C23 C24 H24A 108.9 . . ? C25 C24 H24A 108.9 . . ? C23 C24 H24B 108.9 . . ? C25 C24 H24B 108.9 . . ? H24A C24 H24B 107.7 . . ? N1 C25 C28 107.05(12) . . ? N1 C25 C29 115.75(12) . . ? C28 C25 C29 108.08(13) . . ? N1 C25 C24 106.41(12) . . ? C28 C25 C24 108.55(13) . . ? C29 C25 C24 110.76(13) . . ? C21 C26 H26A 109.5 . . ? C21 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C21 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C21 C27 H27A 109.5 . . ? C21 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C21 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? C25 C28 H28A 109.5 . . ? C25 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C25 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? C25 C29 H29A 109.5 . . ? C25 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? C25 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? 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 C21 N1 O1 C20 -110.41(12) . . . . ? C25 N1 O1 C20 121.35(12) . . . . ? C19 P1 C1 C2 -21.06(15) . . . . ? C7 P1 C1 C2 -141.70(12) . . . . ? C13 P1 C1 C2 106.21(13) . . . . ? C19 P1 C1 C6 163.02(12) . . . . ? C7 P1 C1 C6 42.37(14) . . . . ? C13 P1 C1 C6 -69.72(13) . . . . ? C6 C1 C2 C3 3.1(2) . . . . ? P1 C1 C2 C3 -172.84(12) . . . . ? C1 C2 C3 C4 -1.2(2) . . . . ? C2 C3 C4 C5 -1.6(3) . . . . ? C3 C4 C5 C6 2.3(3) . . . . ? C4 C5 C6 C1 -0.4(2) . . . . ? C2 C1 C6 C5 -2.4(2) . . . . ? P1 C1 C6 C5 173.55(13) . . . . ? C19 P1 C7 C12 135.87(12) . . . . ? C1 P1 C7 C12 -97.71(12) . . . . ? C13 P1 C7 C12 14.35(13) . . . . ? C19 P1 C7 C8 -45.36(13) . . . . ? C1 P1 C7 C8 81.06(13) . . . . ? C13 P1 C7 C8 -166.88(11) . . . . ? C12 C7 C8 C9 -0.6(2) . . . . ? P1 C7 C8 C9 -179.44(12) . . . . ? C7 C8 C9 C10 0.0(2) . . . . ? C8 C9 C10 C11 0.4(2) . . . . ? C9 C10 C11 C12 -0.2(2) . . . . ? C10 C11 C12 C7 -0.5(2) . . . . ? C8 C7 C12 C11 0.9(2) . . . . ? P1 C7 C12 C11 179.64(11) . . . . ? C19 P1 C13 C14 130.50(13) . . . . ? C1 P1 C13 C14 0.86(14) . . . . ? C7 P1 C13 C14 -111.37(13) . . . . ? C19 P1 C13 C18 -50.10(13) . . . . ? C1 P1 C13 C18 -179.75(11) . . . . ? C7 P1 C13 C18 68.03(12) . . . . ? C18 C13 C14 C15 -1.5(2) . . . . ? P1 C13 C14 C15 177.93(12) . . . . ? C13 C14 C15 C16 -0.1(3) . . . . ? C14 C15 C16 C17 1.6(3) . . . . ? C15 C16 C17 C18 -1.6(2) . . . . ? C16 C17 C18 C13 0.0(2) . . . . ? C14 C13 C18 C17 1.5(2) . . . . ? P1 C13 C18 C17 -177.91(11) . . . . ? C1 P1 C19 C20 70.16(13) . . . . ? C7 P1 C19 C20 -170.26(11) . . . . ? C13 P1 C19 C20 -53.42(13) . . . . ? N1 O1 C20 O2 170.70(11) . . . . ? N1 O1 C20 C19 -10.72(18) . . . . ? P1 C19 C20 O2 -6.3(2) . . . . ? P1 C19 C20 O1 175.35(10) . . . . ? O1 N1 C21 C22 -175.75(10) . . . . ? C25 N1 C21 C22 -55.42(15) . . . . ? O1 N1 C21 C26 68.45(12) . . . . ? C25 N1 C21 C26 -171.22(12) . . . . ? O1 N1 C21 C27 -51.65(15) . . . . ? C25 N1 C21 C27 68.68(17) . . . . ? N1 C21 C22 C23 54.63(16) . . . . ? C26 C21 C22 C23 169.53(13) . . . . ? C27 C21 C22 C23 -72.43(17) . . . . ? C21 C22 C23 C24 -58.12(17) . . . . ? C22 C23 C24 C25 57.32(17) . . . . ? O1 N1 C25 C28 -69.59(14) . . . . ? C21 N1 C25 C28 170.33(12) . . . . ? O1 N1 C25 C29 50.97(16) . . . . ? C21 N1 C25 C29 -69.12(17) . . . . ? O1 N1 C25 C24 174.49(10) . . . . ? C21 N1 C25 C24 54.40(16) . . . . ? C23 C24 C25 N1 -52.95(16) . . . . ? C23 C24 C25 C28 -167.85(13) . . . . ? C23 C24 C25 C29 73.64(17) . . . . ? _diffrn_measured_fraction_theta_max 0.937 _diffrn_reflns_theta_full 28.69 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.448 _refine_diff_density_min -0.286 _refine_diff_density_rms 0.051 #============================================================================== #============================================================================== data_saturatedSIPr-BHT _database_code_depnum_ccdc_archive 'CCDC 793075' #TrackingRef 'CIF-final-combined.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C27 H39 N2, C15 H23 O' _chemical_formula_sum 'C42 H62 N2 O' _chemical_formula_weight 610.94 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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) _symmetry_space_group_name_Hall 'P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 10.2181(7) _cell_length_b 19.3153(14) _cell_length_c 19.5555(14) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3859.6(5) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9916 _cell_measurement_theta_min 2.25 _cell_measurement_theta_max 24.85 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.298 _exptl_crystal_size_mid 0.213 _exptl_crystal_size_min 0.201 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.051 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1344 _exptl_absorpt_coefficient_mu 0.061 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9819 _exptl_absorpt_correction_T_max 0.9877 _exptl_absorpt_process_details 'SADABS; Bruker 2009' _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 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 42693 _diffrn_reflns_av_R_equivalents 0.1297 _diffrn_reflns_av_sigmaI/netI 0.0716 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 2.11 _diffrn_reflns_theta_max 26.50 _reflns_number_total 4462 _reflns_number_gt 3148 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _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^)+(0.0504P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0080(12) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_number_reflns 4462 _refine_ls_number_parameters 549 _refine_ls_number_restraints 393 _refine_ls_R_factor_all 0.0675 _refine_ls_R_factor_gt 0.0438 _refine_ls_wR_factor_ref 0.1026 _refine_ls_wR_factor_gt 0.0945 _refine_ls_goodness_of_fit_ref 0.956 _refine_ls_restrained_S_all 1.074 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.4469(2) 0.17281(10) 0.23332(11) 0.0267(5) Uani 1 1 d D . . N2 N 0.2921(2) 0.13740(11) 0.30179(11) 0.0242(5) Uani 1 1 d . . . O1 O 0.47444(19) 0.48721(9) 0.24205(10) 0.0336(5) Uani 1 1 d . . . C1 C 0.3990(3) 0.12041(13) 0.26765(12) 0.0233(6) Uani 1 1 d . A . H1 H 0.443(2) 0.0742(14) 0.2671(13) 0.028 Uiso 1 1 d . . . C2 C 0.3714(3) 0.23668(13) 0.24659(15) 0.0327(7) Uani 1 1 d . A . H2A H 0.3459 0.2598 0.2034 0.039 Uiso 1 1 calc R . . H2B H 0.4215 0.2695 0.2753 0.039 Uiso 1 1 calc R . . C3 C 0.2526(3) 0.20880(13) 0.28437(15) 0.0315(7) Uani 1 1 d . A . H3A H 0.2344 0.2362 0.3261 0.038 Uiso 1 1 calc R . . H3B H 0.1741 0.2091 0.2547 0.038 Uiso 1 1 calc R . . C4A C 0.5646(12) 0.1758(15) 0.1895(6) 0.0348(14) Uani 0.50 1 d PDU A 1 C5A C 0.5537(8) 0.1716(7) 0.1173(5) 0.0376(14) Uani 0.50 1 d PDU A 1 C6A C 0.6721(8) 0.1783(4) 0.0812(4) 0.0373(16) Uani 0.50 1 d PDU A 1 H6A H 0.6699 0.1778 0.0326 0.045 Uiso 0.50 1 calc PR A 1 C7A C 0.7915(7) 0.1857(4) 0.1136(4) 0.0387(15) Uani 0.50 1 d PDU A 1 H7A H 0.8687 0.1899 0.0868 0.046 Uiso 0.50 1 calc PR A 1 C8A C 0.8012(9) 0.1871(4) 0.1844(3) 0.0378(15) Uani 0.50 1 d PDU A 1 H8A H 0.8837 0.1917 0.2063 0.045 Uiso 0.50 1 calc PR A 1 C9A C 0.6849(12) 0.1813(8) 0.2229(4) 0.0356(14) Uani 0.50 1 d PDU A 1 C4B C 0.5527(12) 0.1716(15) 0.1880(6) 0.0352(14) Uani 0.50 1 d PDU A 2 C5B C 0.5177(8) 0.1642(6) 0.1201(5) 0.0368(15) Uani 0.50 1 d PDU A 2 C6B C 0.6147(7) 0.1683(4) 0.0697(4) 0.0391(15) Uani 0.50 1 d PDU A 2 H6B H 0.5940 0.1617 0.0228 0.047 Uiso 0.50 1 calc PR A 2 C7B C 0.7411(8) 0.1823(4) 0.0901(4) 0.0386(16) Uani 0.50 1 d PDU A 2 H7B H 0.8080 0.1859 0.0566 0.046 Uiso 0.50 1 calc PR A 2 C8B C 0.7727(9) 0.1912(5) 0.1586(4) 0.0378(14) Uani 0.50 1 d PDU A 2 H8B H 0.8613 0.1998 0.1707 0.045 Uiso 0.50 1 calc PR A 2 C9B C 0.6780(12) 0.1878(8) 0.2109(4) 0.0371(14) Uani 0.50 1 d PDU A 2 C10 C 0.4010(5) 0.15357(17) 0.08982(16) 0.0691(13) Uani 1 1 d DU . . H10 H 0.3334 0.1494 0.1266 0.083 Uiso 1 1 calc R A 1 C11A C 0.3860(12) 0.2196(5) 0.0413(6) 0.069(3) Uani 0.50 1 d PDU A 1 H11A H 0.3010 0.2179 0.0181 0.104 Uiso 0.50 1 calc PR A 1 H11B H 0.4562 0.2194 0.0071 0.104 Uiso 0.50 1 calc PR A 1 H11C H 0.3917 0.2619 0.0688 0.104 Uiso 0.50 1 calc PR A 1 C12A C 0.4204(12) 0.0900(6) 0.0471(5) 0.074(3) Uani 0.50 1 d PDU A 1 H12A H 0.3371 0.0767 0.0260 0.111 Uiso 0.50 1 calc PR A 1 H12B H 0.4519 0.0521 0.0761 0.111 Uiso 0.50 1 calc PR A 1 H12C H 0.4850 0.0995 0.0113 0.111 Uiso 0.50 1 calc PR A 1 C11B C 0.3268(12) 0.1947(5) 0.0333(6) 0.067(3) Uani 0.50 1 d PDU A 2 H11D H 0.2413 0.1733 0.0252 0.100 Uiso 0.50 1 calc PR A 2 H11E H 0.3780 0.1940 -0.0090 0.100 Uiso 0.50 1 calc PR A 2 H11F H 0.3146 0.2427 0.0483 0.100 Uiso 0.50 1 calc PR A 2 C12B C 0.3694(12) 0.0739(5) 0.0699(5) 0.059(3) Uani 0.50 1 d PDU A 2 H12D H 0.2801 0.0706 0.0519 0.089 Uiso 0.50 1 calc PR A 2 H12E H 0.3774 0.0447 0.1107 0.089 Uiso 0.50 1 calc PR A 2 H12F H 0.4315 0.0581 0.0351 0.089 Uiso 0.50 1 calc PR A 2 C13 C 0.7052(3) 0.19154(17) 0.29272(19) 0.0525(10) Uani 1 1 d D . . H13 H 0.6265 0.1774 0.3198 0.063 Uiso 1 1 calc R A 1 C14A C 0.8173(9) 0.1490(7) 0.3097(8) 0.060(3) Uani 0.50 1 d PD A 1 H14A H 0.8353 0.1525 0.3588 0.090 Uiso 0.50 1 calc PR A 1 H14B H 0.8937 0.1651 0.2838 0.090 Uiso 0.50 1 calc PR A 1 H14C H 0.7988 0.1007 0.2978 0.090 Uiso 0.50 1 calc PR A 1 C15A C 0.7286(11) 0.2726(5) 0.2973(5) 0.058(3) Uani 0.50 1 d PD A 1 H15A H 0.6479 0.2970 0.2849 0.087 Uiso 0.50 1 calc PR A 1 H15B H 0.7988 0.2859 0.2658 0.087 Uiso 0.50 1 calc PR A 1 H15C H 0.7535 0.2850 0.3442 0.087 Uiso 0.50 1 calc PR A 1 C14B C 0.7824(11) 0.1253(6) 0.3258(8) 0.070(4) Uani 0.50 1 d PD A 2 H14D H 0.7949 0.1329 0.3749 0.105 Uiso 0.50 1 calc PR A 2 H14E H 0.8679 0.1203 0.3036 0.105 Uiso 0.50 1 calc PR A 2 H14F H 0.7308 0.0832 0.3186 0.105 Uiso 0.50 1 calc PR A 2 C15B C 0.7708(12) 0.2552(5) 0.3256(5) 0.061(3) Uani 0.50 1 d PD A 2 H15D H 0.7768 0.2485 0.3751 0.092 Uiso 0.50 1 calc PR A 2 H15E H 0.7185 0.2966 0.3159 0.092 Uiso 0.50 1 calc PR A 2 H15F H 0.8589 0.2611 0.3065 0.092 Uiso 0.50 1 calc PR A 2 C16 C 0.1998(3) 0.08990(14) 0.33250(14) 0.0275(7) Uani 1 1 d . A . C17 C 0.1668(3) 0.09989(14) 0.40139(14) 0.0306(7) Uani 1 1 d . . . C18 C 0.0712(3) 0.05713(16) 0.42896(16) 0.0407(8) Uani 1 1 d . A . H18 H 0.0467 0.0627 0.4755 0.049 Uiso 1 1 calc R . . C19 C 0.0111(3) 0.00675(17) 0.39015(19) 0.0493(9) Uani 1 1 d . . . H19 H -0.0542 -0.0220 0.4099 0.059 Uiso 1 1 calc R A . C20 C 0.0458(3) -0.00180(17) 0.32323(19) 0.0480(9) Uani 1 1 d . A . H20 H 0.0036 -0.0367 0.2971 0.058 Uiso 1 1 calc R . . C21 C 0.1408(3) 0.03893(15) 0.29219(15) 0.0361(8) Uani 1 1 d . . . C22 C 0.2267(3) 0.15553(16) 0.44586(15) 0.0398(8) Uani 1 1 d . A . H22 H 0.3002 0.1772 0.4198 0.048 Uiso 1 1 calc R . . C23 C 0.2825(4) 0.1261(2) 0.51260(16) 0.0551(10) Uani 1 1 d . . . H23A H 0.2105 0.1124 0.5428 0.083 Uiso 1 1 calc R A . H23B H 0.3359 0.1614 0.5353 0.083 Uiso 1 1 calc R . . H23C H 0.3368 0.0856 0.5024 0.083 Uiso 1 1 calc R . . C24 C 0.1272(4) 0.21195(17) 0.46233(18) 0.0549(10) Uani 1 1 d . . . H24A H 0.1684 0.2473 0.4911 0.082 Uiso 1 1 calc R A . H24B H 0.0528 0.1916 0.4867 0.082 Uiso 1 1 calc R . . H24C H 0.0965 0.2332 0.4197 0.082 Uiso 1 1 calc R . . C25 C 0.1724(4) 0.02824(16) 0.21702(16) 0.0467(9) Uani 1 1 d DU A . H25 H 0.2495 0.0565 0.2024 0.056 Uiso 1 1 calc R B 1 C26A C 0.0443(10) 0.0511(7) 0.1794(6) 0.072(4) Uani 0.50 1 d PD A 1 H26A H 0.0560 0.0458 0.1299 0.108 Uiso 0.50 1 calc PR A 1 H26B H 0.0257 0.0997 0.1901 0.108 Uiso 0.50 1 calc PR A 1 H26C H -0.0288 0.0222 0.1947 0.108 Uiso 0.50 1 calc PR A 1 C27A C 0.1961(17) -0.0491(6) 0.2066(8) 0.056(3) Uani 0.50 1 d PDU A 1 H27A H 0.2162 -0.0580 0.1584 0.084 Uiso 0.50 1 calc PR A 1 H27B H 0.1174 -0.0749 0.2196 0.084 Uiso 0.50 1 calc PR A 1 H27C H 0.2698 -0.0640 0.2350 0.084 Uiso 0.50 1 calc PR A 1 C26B C 0.1002(11) 0.0756(6) 0.1677(6) 0.059(3) Uani 0.50 1 d PD A 2 H26D H 0.1011 0.1231 0.1855 0.089 Uiso 0.50 1 calc PR A 2 H26E H 0.0095 0.0599 0.1628 0.089 Uiso 0.50 1 calc PR A 2 H26F H 0.1435 0.0745 0.1230 0.089 Uiso 0.50 1 calc PR A 2 C27B C 0.1707(18) -0.0453(6) 0.1895(8) 0.058(3) Uani 0.50 1 d PDU A 2 H27D H 0.1914 -0.0447 0.1406 0.087 Uiso 0.50 1 calc PR A 2 H27E H 0.0836 -0.0654 0.1963 0.087 Uiso 0.50 1 calc PR A 2 H27F H 0.2359 -0.0731 0.2138 0.087 Uiso 0.50 1 calc PR A 2 C28 C 0.3823(3) 0.44476(14) 0.22289(14) 0.0274(6) Uani 1 1 d . C . C29 C 0.2927(3) 0.41487(12) 0.27120(14) 0.0253(6) Uani 1 1 d . . . C30 C 0.1902(3) 0.37414(13) 0.24825(15) 0.0280(6) Uani 1 1 d . . . H30 H 0.1296 0.3568 0.2809 0.034 Uiso 1 1 calc R . . C31 C 0.1716(3) 0.35735(14) 0.17963(15) 0.0284(7) Uani 1 1 d . . . C32 C 0.2625(3) 0.38250(15) 0.13396(15) 0.0326(7) Uani 1 1 d . C . H32 H 0.2532 0.3705 0.0871 0.039 Uiso 1 1 calc R . . C33 C 0.3675(3) 0.42462(16) 0.15266(14) 0.0357(7) Uani 1 1 d D . . C34 C 0.3128(3) 0.42856(14) 0.34842(14) 0.0318(7) Uani 1 1 d . . . C35 C 0.2110(4) 0.39153(17) 0.39306(16) 0.0510(9) Uani 1 1 d . . . H35A H 0.2280 0.4018 0.4413 0.076 Uiso 1 1 calc R . . H35B H 0.2168 0.3415 0.3855 0.076 Uiso 1 1 calc R . . H35C H 0.1232 0.4077 0.3808 0.076 Uiso 1 1 calc R . . C36 C 0.3018(4) 0.50592(15) 0.36459(17) 0.0490(9) Uani 1 1 d . . . H36A H 0.2150 0.5227 0.3511 0.074 Uiso 1 1 calc R . . H36B H 0.3691 0.5314 0.3392 0.074 Uiso 1 1 calc R . . H36C H 0.3142 0.5132 0.4138 0.074 Uiso 1 1 calc R . . C37 C 0.4479(3) 0.40247(16) 0.36932(15) 0.0446(9) Uani 1 1 d . . . H37A H 0.5147 0.4251 0.3412 0.067 Uiso 1 1 calc R . . H37B H 0.4523 0.3522 0.3626 0.067 Uiso 1 1 calc R . . H37C H 0.4633 0.4133 0.4176 0.067 Uiso 1 1 calc R . . C38 C 0.0574(3) 0.31392(15) 0.15650(16) 0.0393(8) Uani 1 1 d . . . H38A H 0.0897 0.2733 0.1316 0.059 Uiso 1 1 calc R . . H38B H 0.0011 0.3414 0.1264 0.059 Uiso 1 1 calc R . . H38C H 0.0071 0.2987 0.1965 0.059 Uiso 1 1 calc R . . C39A C 0.4537(5) 0.4577(3) 0.0996(2) 0.0373(12) Uani 0.723(7) 1 d PDU C 1 C40A C 0.5986(5) 0.4404(3) 0.1154(3) 0.0478(15) Uani 0.723(7) 1 d PDU C 1 H40A H 0.6551 0.4625 0.0813 0.072 Uiso 0.723(7) 1 calc PR C 1 H40B H 0.6112 0.3901 0.1139 0.072 Uiso 0.723(7) 1 calc PR C 1 H40C H 0.6212 0.4576 0.1610 0.072 Uiso 0.723(7) 1 calc PR C 1 C41A C 0.4327(6) 0.5375(3) 0.0964(3) 0.0480(15) Uani 0.723(7) 1 d PDU C 1 H41A H 0.3465 0.5475 0.0768 0.072 Uiso 0.723(7) 1 calc PR C 1 H41B H 0.5008 0.5585 0.0679 0.072 Uiso 0.723(7) 1 calc PR C 1 H41C H 0.4375 0.5569 0.1427 0.072 Uiso 0.723(7) 1 calc PR C 1 C42A C 0.4214(5) 0.4315(3) 0.0281(2) 0.0598(17) Uani 0.723(7) 1 d PDU C 1 H42A H 0.4772 0.4550 -0.0054 0.090 Uiso 0.723(7) 1 calc PR C 1 H42B H 0.3294 0.4411 0.0178 0.090 Uiso 0.723(7) 1 calc PR C 1 H42C H 0.4369 0.3814 0.0259 0.090 Uiso 0.723(7) 1 calc PR C 1 C39B C 0.4972(5) 0.4268(3) 0.0995(2) 0.045(2) Uani 0.277(7) 1 d PRDU C 2 C40B C 0.6155(5) 0.4007(3) 0.1311(2) 0.053(3) Uani 0.277(7) 1 d PRDU C 2 H40D H 0.6297 0.4243 0.1748 0.080 Uiso 0.277(7) 1 calc PR C 2 H40E H 0.6902 0.4092 0.1008 0.080 Uiso 0.277(7) 1 calc PR C 2 H40F H 0.6066 0.3508 0.1390 0.080 Uiso 0.277(7) 1 calc PR C 2 C41B C 0.4946(15) 0.5058(6) 0.0832(7) 0.051(3) Uani 0.277(7) 1 d PDU C 2 H41D H 0.4710 0.5316 0.1246 0.077 Uiso 0.277(7) 1 calc PR C 2 H41E H 0.4300 0.5149 0.0473 0.077 Uiso 0.277(7) 1 calc PR C 2 H41F H 0.5814 0.5206 0.0675 0.077 Uiso 0.277(7) 1 calc PR C 2 C42B C 0.4701(13) 0.3934(7) 0.0284(5) 0.041(3) Uani 0.277(7) 1 d PDU C 2 H42D H 0.3873 0.4111 0.0102 0.062 Uiso 0.277(7) 1 calc PR C 2 H42E H 0.4647 0.3430 0.0334 0.062 Uiso 0.277(7) 1 calc PR C 2 H42F H 0.5414 0.4051 -0.0031 0.062 Uiso 0.277(7) 1 calc PR C 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0423(14) 0.0175(11) 0.0205(12) 0.0010(9) 0.0080(11) 0.0026(10) N2 0.0312(13) 0.0211(12) 0.0204(12) 0.0010(9) 0.0016(11) 0.0027(10) O1 0.0351(12) 0.0329(11) 0.0326(11) -0.0007(9) -0.0058(10) -0.0108(9) C1 0.0352(16) 0.0209(14) 0.0137(13) -0.0010(11) -0.0019(12) 0.0017(13) C2 0.0464(18) 0.0195(14) 0.0321(16) -0.0013(12) 0.0102(15) 0.0071(13) C3 0.0411(18) 0.0219(14) 0.0317(16) 0.0028(12) 0.0089(14) 0.0074(13) C4A 0.058(3) 0.016(3) 0.030(2) 0.004(2) 0.027(2) 0.005(3) C5A 0.063(3) 0.020(2) 0.030(2) 0.008(2) 0.027(3) 0.007(3) C6A 0.058(4) 0.022(2) 0.032(3) 0.003(2) 0.025(3) -0.001(3) C7A 0.055(3) 0.025(2) 0.035(3) 0.002(3) 0.026(3) -0.005(3) C8A 0.057(3) 0.020(2) 0.037(3) 0.002(3) 0.025(3) -0.003(2) C9A 0.050(2) 0.016(2) 0.040(3) 0.004(2) 0.028(2) -0.002(2) C4B 0.059(3) 0.016(3) 0.031(2) 0.003(2) 0.025(2) 0.004(2) C5B 0.062(3) 0.018(3) 0.030(2) 0.007(2) 0.031(3) 0.010(3) C6B 0.059(4) 0.026(3) 0.033(3) 0.006(2) 0.029(3) 0.005(3) C7B 0.057(4) 0.025(2) 0.034(3) 0.005(2) 0.026(3) 0.002(3) C8B 0.054(3) 0.023(2) 0.036(3) 0.004(3) 0.025(3) -0.001(2) C9B 0.055(3) 0.016(3) 0.040(3) 0.003(2) 0.030(3) -0.002(2) C10 0.137(4) 0.049(2) 0.0219(17) 0.0003(15) -0.003(2) 0.050(2) C11A 0.113(9) 0.069(7) 0.026(4) 0.010(5) -0.004(6) 0.046(6) C12A 0.107(9) 0.075(7) 0.040(6) -0.019(5) -0.030(5) 0.049(6) C11B 0.107(9) 0.054(6) 0.039(5) 0.009(5) -0.003(6) 0.027(5) C12B 0.092(7) 0.052(5) 0.034(6) -0.020(4) -0.002(5) 0.032(5) C13 0.0347(19) 0.050(2) 0.072(3) -0.0272(19) 0.0162(19) -0.0132(17) C14A 0.018(4) 0.096(10) 0.066(8) -0.023(6) 0.010(4) -0.013(5) C15A 0.059(7) 0.069(7) 0.046(6) -0.033(5) 0.019(5) -0.031(5) C14B 0.047(8) 0.089(10) 0.074(9) -0.021(6) -0.007(7) 0.004(6) C15B 0.063(7) 0.068(7) 0.053(7) -0.026(5) -0.003(5) -0.030(6) C16 0.0291(15) 0.0254(15) 0.0278(16) 0.0057(12) -0.0033(13) 0.0003(13) C17 0.0293(16) 0.0325(16) 0.0300(16) 0.0064(13) 0.0019(13) 0.0012(13) C18 0.0383(19) 0.0442(19) 0.0396(18) 0.0146(15) 0.0043(15) -0.0004(16) C19 0.044(2) 0.043(2) 0.061(2) 0.0193(19) -0.0075(18) -0.0138(17) C20 0.049(2) 0.0351(18) 0.060(2) 0.0092(17) -0.0237(19) -0.0120(17) C21 0.0417(19) 0.0265(16) 0.0401(18) 0.0059(13) -0.0138(15) -0.0020(15) C22 0.047(2) 0.0452(19) 0.0273(16) -0.0018(14) 0.0140(15) -0.0095(16) C23 0.061(2) 0.080(3) 0.0252(17) -0.0080(17) 0.0071(17) -0.001(2) C24 0.073(3) 0.045(2) 0.047(2) 0.0004(16) 0.032(2) -0.0050(19) C25 0.064(2) 0.0380(18) 0.0386(18) -0.0074(14) -0.0201(17) -0.0026(17) C26A 0.084(9) 0.103(11) 0.030(6) -0.005(6) -0.023(6) 0.036(7) C27A 0.057(6) 0.055(5) 0.055(7) -0.021(4) -0.014(5) 0.007(4) C26B 0.076(8) 0.066(7) 0.036(5) 0.004(4) -0.010(5) 0.002(6) C27B 0.071(6) 0.048(4) 0.056(6) -0.013(4) -0.017(5) 0.006(4) C28 0.0286(16) 0.0241(14) 0.0296(15) 0.0031(12) -0.0068(13) -0.0009(13) C29 0.0302(15) 0.0164(13) 0.0292(15) -0.0001(11) -0.0032(13) 0.0030(12) C30 0.0281(15) 0.0212(14) 0.0348(16) 0.0015(12) 0.0048(14) 0.0008(12) C31 0.0270(15) 0.0216(14) 0.0368(17) 0.0006(12) -0.0062(13) -0.0001(12) C32 0.0347(17) 0.0361(16) 0.0268(15) 0.0021(13) -0.0099(13) -0.0066(14) C33 0.0374(18) 0.0437(18) 0.0260(16) 0.0041(13) -0.0077(14) -0.0118(15) C34 0.0436(19) 0.0217(14) 0.0300(16) -0.0054(12) 0.0030(14) -0.0051(14) C35 0.080(3) 0.0405(18) 0.0323(18) -0.0075(15) 0.0125(18) -0.0216(19) C36 0.067(2) 0.0284(16) 0.052(2) -0.0124(15) 0.0166(18) -0.0056(17) C37 0.064(2) 0.0420(19) 0.0277(16) -0.0055(14) -0.0162(17) 0.0029(17) C38 0.0384(18) 0.0347(17) 0.0448(18) -0.0019(14) -0.0064(16) -0.0052(15) C39A 0.040(2) 0.049(3) 0.0224(19) -0.004(2) 0.0029(19) -0.019(2) C40A 0.046(3) 0.054(3) 0.044(3) -0.018(2) 0.013(2) -0.025(3) C41A 0.052(3) 0.055(3) 0.036(3) 0.015(2) 0.001(2) -0.022(3) C42A 0.062(4) 0.084(4) 0.033(3) -0.007(3) 0.010(3) -0.030(3) C39B 0.051(4) 0.056(4) 0.027(3) -0.006(4) 0.006(4) -0.020(4) C40B 0.044(6) 0.074(7) 0.041(6) -0.007(6) 0.022(5) -0.032(6) C41B 0.066(6) 0.058(6) 0.030(5) 0.000(5) -0.008(5) -0.020(5) C42B 0.042(5) 0.060(6) 0.022(4) -0.009(5) 0.014(4) -0.012(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C1 1.309(3) . ? N1 C4B 1.399(9) . ? N1 C2 1.478(3) . ? N1 C4A 1.478(9) . ? N2 C1 1.321(3) . ? N2 C16 1.446(3) . ? N2 C3 1.477(3) . ? O1 C28 1.303(3) . ? C1 H1 1.00(3) . ? C2 C3 1.519(4) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4A C9A 1.397(11) . ? C4A C5A 1.417(11) . ? C5A C6A 1.407(9) . ? C5A C10 1.688(9) . ? C6A C7A 1.382(9) . ? C6A H6A 0.9500 . ? C7A C8A 1.388(8) . ? C7A H7A 0.9500 . ? C8A C9A 1.411(10) . ? C8A H8A 0.9500 . ? C9A C13 1.395(9) . ? C4B C5B 1.383(11) . ? C4B C9B 1.392(11) . ? C5B C10 1.347(9) . ? C5B C6B 1.400(9) . ? C6B C7B 1.378(9) . ? C6B H6B 0.9500 . ? C7B C8B 1.389(9) . ? C7B H7B 0.9500 . ? C8B C9B 1.409(10) . ? C8B H8B 0.9500 . ? C9B C13 1.626(9) . ? C10 C12A 1.499(10) . ? C10 C11B 1.557(10) . ? C10 C11A 1.597(10) . ? C10 C12B 1.620(10) . ? C10 H10 1.0000 . ? C11A H11A 0.9800 . ? C11A H11B 0.9800 . ? C11A H11C 0.9800 . ? C12A H12A 0.9800 . ? C12A H12B 0.9800 . ? C12A H12C 0.9800 . ? C11B H11D 0.9800 . ? C11B H11E 0.9800 . ? C11B H11F 0.9800 . ? C12B H12D 0.9800 . ? C12B H12E 0.9800 . ? C12B H12F 0.9800 . ? C13 C14A 1.448(11) . ? C13 C15B 1.542(9) . ? C13 C15A 1.586(10) . ? C13 C14B 1.636(11) . ? C13 H13 1.0000 . ? C14A H14A 0.9800 . ? C14A H14B 0.9800 . ? C14A H14C 0.9800 . ? C15A H15A 0.9800 . ? C15A H15B 0.9800 . ? C15A H15C 0.9800 . ? C14B H14D 0.9800 . ? C14B H14E 0.9800 . ? C14B H14F 0.9800 . ? C15B H15D 0.9800 . ? C15B H15E 0.9800 . ? C15B H15F 0.9800 . ? C16 C21 1.398(4) . ? C16 C17 1.402(4) . ? C17 C18 1.388(4) . ? C17 C22 1.512(4) . ? C18 C19 1.378(5) . ? C18 H18 0.9500 . ? C19 C20 1.366(5) . ? C19 H19 0.9500 . ? C20 C21 1.389(4) . ? C20 H20 0.9500 . ? C21 C25 1.519(4) . ? C22 C24 1.524(4) . ? C22 C23 1.534(4) . ? C22 H22 1.0000 . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? C25 C27B 1.519(12) . ? C25 C26B 1.521(10) . ? C25 C27A 1.527(12) . ? C25 C26A 1.565(10) . ? C25 H25 1.0000 . ? C26A H26A 0.9800 . ? C26A H26B 0.9800 . ? C26A H26C 0.9800 . ? C27A H27A 0.9800 . ? C27A H27B 0.9800 . ? C27A H27C 0.9800 . ? C26B H26D 0.9800 . ? C26B H26E 0.9800 . ? C26B H26F 0.9800 . ? C27B H27D 0.9800 . ? C27B H27E 0.9800 . ? C27B H27F 0.9800 . ? C28 C33 1.435(4) . ? C28 C29 1.437(4) . ? C29 C30 1.384(4) . ? C29 C34 1.547(4) . ? C30 C31 1.394(4) . ? C30 H30 0.9500 . ? C31 C32 1.377(4) . ? C31 C38 1.507(4) . ? C32 C33 1.395(4) . ? C32 H32 0.9500 . ? C33 C39A 1.503(5) . ? C33 C39B 1.685(5) . ? C34 C37 1.525(4) . ? C34 C36 1.531(4) . ? C34 C35 1.535(4) . ? C35 H35A 0.9800 . ? C35 H35B 0.9800 . ? C35 H35C 0.9800 . ? C36 H36A 0.9800 . ? C36 H36B 0.9800 . ? C36 H36C 0.9800 . ? C37 H37A 0.9800 . ? C37 H37B 0.9800 . ? C37 H37C 0.9800 . ? C38 H38A 0.9800 . ? C38 H38B 0.9800 . ? C38 H38C 0.9800 . ? C39A C42A 1.524(6) . ? C39A C40A 1.549(6) . ? C39A C41A 1.558(7) . ? C40A H40A 0.9800 . ? C40A H40B 0.9800 . ? C40A H40C 0.9800 . ? C41A H41A 0.9800 . ? C41A H41B 0.9800 . ? C41A H41C 0.9800 . ? C42A H42A 0.9800 . ? C42A H42B 0.9800 . ? C42A H42C 0.9800 . ? C39B C40B 1.4486 . ? C39B C42B 1.557(11) . ? C39B C41B 1.559(12) . ? C40B H40D 0.9800 . ? C40B H40E 0.9800 . ? C40B H40F 0.9800 . ? C41B H41D 0.9800 . ? C41B H41E 0.9800 . ? C41B H41F 0.9800 . ? C42B H42D 0.9800 . ? C42B H42E 0.9800 . ? C42B H42F 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 N1 C4B 126.9(12) . . ? C1 N1 C2 111.1(2) . . ? C4B N1 C2 122.0(12) . . ? C1 N1 C4A 129.2(12) . . ? C2 N1 C4A 119.6(12) . . ? C1 N2 C16 126.2(2) . . ? C1 N2 C3 109.9(2) . . ? C16 N2 C3 120.7(2) . . ? N1 C1 N2 112.1(2) . . ? N1 C1 H1 121.3(15) . . ? N2 C1 H1 126.6(15) . . ? N1 C2 C3 101.9(2) . . ? N1 C2 H2A 111.4 . . ? C3 C2 H2A 111.4 . . ? N1 C2 H2B 111.4 . . ? C3 C2 H2B 111.4 . . ? H2A C2 H2B 109.3 . . ? N2 C3 C2 103.0(2) . . ? N2 C3 H3A 111.2 . . ? C2 C3 H3A 111.2 . . ? N2 C3 H3B 111.2 . . ? C2 C3 H3B 111.2 . . ? H3A C3 H3B 109.1 . . ? C9A C4A C5A 122.6(7) . . ? C9A C4A N1 116.6(9) . . ? C5A C4A N1 120.8(9) . . ? C6A C5A C4A 115.3(7) . . ? C6A C5A C10 130.9(7) . . ? C4A C5A C10 113.7(7) . . ? C7A C6A C5A 122.6(6) . . ? C7A C6A H6A 118.7 . . ? C5A C6A H6A 118.7 . . ? C6A C7A C8A 121.5(6) . . ? C6A C7A H7A 119.3 . . ? C8A C7A H7A 119.3 . . ? C7A C8A C9A 118.1(7) . . ? C7A C8A H8A 121.0 . . ? C9A C8A H8A 121.0 . . ? C13 C9A C4A 126.8(9) . . ? C13 C9A C8A 112.7(8) . . ? C4A C9A C8A 119.8(7) . . ? C5B C4B C9B 124.8(7) . . ? C5B C4B N1 114.2(9) . . ? C9B C4B N1 120.2(10) . . ? C10 C5B C4B 131.8(7) . . ? C10 C5B C6B 109.1(7) . . ? C4B C5B C6B 119.1(7) . . ? C7B C6B C5B 118.2(7) . . ? C7B C6B H6B 120.9 . . ? C5B C6B H6B 120.9 . . ? C6B C7B C8B 121.4(7) . . ? C6B C7B H7B 119.3 . . ? C8B C7B H7B 119.3 . . ? C7B C8B C9B 122.3(7) . . ? C7B C8B H8B 118.9 . . ? C9B C8B H8B 118.9 . . ? C4B C9B C8B 114.1(7) . . ? C4B C9B C13 118.9(9) . . ? C8B C9B C13 126.5(8) . . ? C5B C10 C12A 104.6(8) . . ? C5B C10 C11B 131.6(7) . . ? C12A C10 C11B 95.0(7) . . ? C5B C10 C11A 102.9(7) . . ? C12A C10 C11A 109.6(6) . . ? C5B C10 C12B 115.3(8) . . ? C11B C10 C12B 102.6(6) . . ? C11A C10 C12B 126.6(6) . . ? C12A C10 C5A 103.0(7) . . ? C11B C10 C5A 124.8(6) . . ? C11A C10 C5A 96.5(6) . . ? C12B C10 C5A 117.2(7) . . ? C5B C10 H10 107.9 . . ? C12A C10 H10 115.2 . . ? C11B C10 H10 102.4 . . ? C11A C10 H10 115.2 . . ? C12B C10 H10 87.6 . . ? C5A C10 H10 115.2 . . ? C10 C11A H11A 109.5 . . ? C10 C11A H11B 109.5 . . ? H11A C11A H11B 109.5 . . ? C10 C11A H11C 109.5 . . ? H11A C11A H11C 109.5 . . ? H11B C11A H11C 109.5 . . ? C10 C12A H12A 109.5 . . ? C10 C12A H12B 109.5 . . ? H12A C12A H12B 109.5 . . ? C10 C12A H12C 109.5 . . ? H12A C12A H12C 109.5 . . ? H12B C12A H12C 109.5 . . ? C10 C11B H11D 109.5 . . ? C10 C11B H11E 109.5 . . ? H11D C11B H11E 109.5 . . ? C10 C11B H11F 109.5 . . ? H11D C11B H11F 109.5 . . ? H11E C11B H11F 109.5 . . ? C10 C12B H12D 109.5 . . ? C10 C12B H12E 109.5 . . ? H12D C12B H12E 109.5 . . ? C10 C12B H12F 109.5 . . ? H12D C12B H12F 109.5 . . ? H12E C12B H12F 109.5 . . ? C9A C13 C14A 105.1(9) . . ? C9A C13 C15B 125.8(7) . . ? C14A C13 C15B 90.7(7) . . ? C9A C13 C15A 102.6(7) . . ? C14A C13 C15A 115.3(7) . . ? C14A C13 C9B 109.6(9) . . ? C15B C13 C9B 121.3(7) . . ? C15A C13 C9B 97.2(7) . . ? C9A C13 C14B 110.3(9) . . ? C15B C13 C14B 104.4(7) . . ? C15A C13 C14B 132.5(7) . . ? C9B C13 C14B 115.9(8) . . ? C9A C13 H13 111.1 . . ? C14A C13 H13 111.1 . . ? C15B C13 H13 110.3 . . ? C15A C13 H13 111.1 . . ? C9B C13 H13 111.8 . . ? C14B C13 H13 88.0 . . ? C13 C14A H14A 109.5 . . ? C13 C14A H14B 109.5 . . ? H14A C14A H14B 109.5 . . ? C13 C14A H14C 109.5 . . ? H14A C14A H14C 109.5 . . ? H14B C14A H14C 109.5 . . ? C13 C15A H15A 109.5 . . ? C13 C15A H15B 109.5 . . ? H15A C15A H15B 109.5 . . ? C13 C15A H15C 109.5 . . ? H15A C15A H15C 109.5 . . ? H15B C15A H15C 109.5 . . ? C13 C14B H14D 109.5 . . ? C13 C14B H14E 109.5 . . ? H14D C14B H14E 109.5 . . ? C13 C14B H14F 109.5 . . ? H14D C14B H14F 109.5 . . ? H14E C14B H14F 109.5 . . ? C13 C15B H15D 109.5 . . ? C13 C15B H15E 109.5 . . ? H15D C15B H15E 109.5 . . ? C13 C15B H15F 109.5 . . ? H15D C15B H15F 109.5 . . ? H15E C15B H15F 109.5 . . ? C21 C16 C17 122.3(3) . . ? C21 C16 N2 119.6(2) . . ? C17 C16 N2 117.9(2) . . ? C18 C17 C16 117.4(3) . . ? C18 C17 C22 119.0(3) . . ? C16 C17 C22 123.6(3) . . ? C19 C18 C17 121.3(3) . . ? C19 C18 H18 119.3 . . ? C17 C18 H18 119.3 . . ? C20 C19 C18 119.8(3) . . ? C20 C19 H19 120.1 . . ? C18 C19 H19 120.1 . . ? C19 C20 C21 122.1(3) . . ? C19 C20 H20 118.9 . . ? C21 C20 H20 118.9 . . ? C20 C21 C16 117.0(3) . . ? C20 C21 C25 119.6(3) . . ? C16 C21 C25 123.3(3) . . ? C17 C22 C24 111.1(3) . . ? C17 C22 C23 112.1(3) . . ? C24 C22 C23 109.5(3) . . ? C17 C22 H22 108.0 . . ? C24 C22 H22 108.0 . . ? C23 C22 H22 108.0 . . ? C22 C23 H23A 109.5 . . ? C22 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C22 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C22 C24 H24A 109.5 . . ? C22 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C22 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C27B C25 C21 117.9(7) . . ? C27B C25 C26B 109.4(8) . . ? C21 C25 C26B 115.4(6) . . ? C21 C25 C27A 107.2(7) . . ? C26B C25 C27A 125.5(8) . . ? C27B C25 C26A 95.0(8) . . ? C21 C25 C26A 103.8(5) . . ? C27A C25 C26A 110.2(8) . . ? C27B C25 H25 114.7 . . ? C21 C25 H25 111.7 . . ? C26B C25 H25 82.7 . . ? C27A C25 H25 111.7 . . ? C26A C25 H25 111.7 . . ? C25 C26A H26A 109.5 . . ? C25 C26A H26B 109.5 . . ? H26A C26A H26B 109.5 . . ? C25 C26A H26C 109.5 . . ? H26A C26A H26C 109.5 . . ? H26B C26A H26C 109.5 . . ? C25 C27A H27A 109.5 . . ? C25 C27A H27B 109.5 . . ? H27A C27A H27B 109.5 . . ? C25 C27A H27C 109.5 . . ? H27A C27A H27C 109.5 . . ? H27B C27A H27C 109.5 . . ? C25 C26B H26D 109.5 . . ? C25 C26B H26E 109.5 . . ? H26D C26B H26E 109.5 . . ? C25 C26B H26F 109.5 . . ? H26D C26B H26F 109.5 . . ? H26E C26B H26F 109.5 . . ? C25 C27B H27D 109.5 . . ? C25 C27B H27E 109.5 . . ? H27D C27B H27E 109.5 . . ? C25 C27B H27F 109.5 . . ? H27D C27B H27F 109.5 . . ? H27E C27B H27F 109.5 . . ? O1 C28 C33 121.4(3) . . ? O1 C28 C29 121.6(2) . . ? C33 C28 C29 116.9(2) . . ? C30 C29 C28 119.8(2) . . ? C30 C29 C34 121.0(2) . . ? C28 C29 C34 119.2(2) . . ? C29 C30 C31 123.2(3) . . ? C29 C30 H30 118.4 . . ? C31 C30 H30 118.4 . . ? C32 C31 C30 116.8(3) . . ? C32 C31 C38 121.6(3) . . ? C30 C31 C38 121.6(3) . . ? C31 C32 C33 123.7(3) . . ? C31 C32 H32 118.2 . . ? C33 C32 H32 118.2 . . ? C32 C33 C28 119.3(3) . . ? C32 C33 C39A 121.2(3) . . ? C28 C33 C39A 118.9(3) . . ? C32 C33 C39B 117.2(3) . . ? C28 C33 C39B 120.1(3) . . ? C37 C34 C36 109.5(3) . . ? C37 C34 C35 107.9(3) . . ? C36 C34 C35 106.7(2) . . ? C37 C34 C29 109.0(2) . . ? C36 C34 C29 111.0(2) . . ? C35 C34 C29 112.7(2) . . ? C34 C35 H35A 109.5 . . ? C34 C35 H35B 109.5 . . ? H35A C35 H35B 109.5 . . ? C34 C35 H35C 109.5 . . ? H35A C35 H35C 109.5 . . ? H35B C35 H35C 109.5 . . ? C34 C36 H36A 109.5 . . ? C34 C36 H36B 109.5 . . ? H36A C36 H36B 109.5 . . ? C34 C36 H36C 109.5 . . ? H36A C36 H36C 109.5 . . ? H36B C36 H36C 109.5 . . ? C34 C37 H37A 109.5 . . ? C34 C37 H37B 109.5 . . ? H37A C37 H37B 109.5 . . ? C34 C37 H37C 109.5 . . ? H37A C37 H37C 109.5 . . ? H37B C37 H37C 109.5 . . ? C31 C38 H38A 109.5 . . ? C31 C38 H38B 109.5 . . ? H38A C38 H38B 109.5 . . ? C31 C38 H38C 109.5 . . ? H38A C38 H38C 109.5 . . ? H38B C38 H38C 109.5 . . ? C33 C39A C42A 111.4(3) . . ? C33 C39A C40A 109.3(4) . . ? C42A C39A C40A 108.5(4) . . ? C33 C39A C41A 111.5(4) . . ? C42A C39A C41A 105.2(4) . . ? C40A C39A C41A 110.7(4) . . ? C39A C40A H40A 109.5 . . ? C39A C40A H40B 109.5 . . ? H40A C40A H40B 109.5 . . ? C39A C40A H40C 109.5 . . ? H40A C40A H40C 109.5 . . ? H40B C40A H40C 109.5 . . ? C39A C41A H41A 109.5 . . ? C39A C41A H41B 109.5 . . ? H41A C41A H41B 109.5 . . ? C39A C41A H41C 109.5 . . ? H41A C41A H41C 109.5 . . ? H41B C41A H41C 109.5 . . ? C39A C42A H42A 109.5 . . ? C39A C42A H42B 109.5 . . ? H42A C42A H42B 109.5 . . ? C39A C42A H42C 109.5 . . ? H42A C42A H42C 109.5 . . ? H42B C42A H42C 109.5 . . ? C40B C39B C42B 112.6(4) . . ? C40B C39B C41B 116.3(6) . . ? C42B C39B C41B 102.8(7) . . ? C40B C39B C33 112.6(2) . . ? C42B C39B C33 113.6(6) . . ? C41B C39B C33 97.9(6) . . ? C39B C40B H40D 109.5 . . ? C39B C40B H40E 109.5 . . ? H40D C40B H40E 109.5 . . ? C39B C40B H40F 109.5 . . ? H40D C40B H40F 109.5 . . ? H40E C40B H40F 109.5 . . ? C39B C41B H41D 109.5 . . ? C39B C41B H41E 109.5 . . ? H41D C41B H41E 109.5 . . ? C39B C41B H41F 109.5 . . ? H41D C41B H41F 109.5 . . ? H41E C41B H41F 109.5 . . ? C39B C42B H42D 109.5 . . ? C39B C42B H42E 109.5 . . ? H42D C42B H42E 109.5 . . ? C39B C42B H42F 109.5 . . ? H42D C42B H42F 109.5 . . ? H42E C42B H42F 109.5 . . ? 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 C4B N1 C1 N2 -174.8(7) . . . . ? C2 N1 C1 N2 3.6(3) . . . . ? C4A N1 C1 N2 179.5(7) . . . . ? C16 N2 C1 N1 165.8(2) . . . . ? C3 N2 C1 N1 6.0(3) . . . . ? C1 N1 C2 C3 -11.0(3) . . . . ? C4B N1 C2 C3 167.5(6) . . . . ? C4A N1 C2 C3 172.7(6) . . . . ? C1 N2 C3 C2 -12.4(3) . . . . ? C16 N2 C3 C2 -173.6(2) . . . . ? N1 C2 C3 N2 13.2(3) . . . . ? C1 N1 C4A C9A -79(2) . . . . ? C4B N1 C4A C9A -144(27) . . . . ? C2 N1 C4A C9A 97(2) . . . . ? C1 N1 C4A C5A 99.9(19) . . . . ? C4B N1 C4A C5A 35(23) . . . . ? C2 N1 C4A C5A -85(2) . . . . ? C9A C4A C5A C6A -4(3) . . . . ? N1 C4A C5A C6A 177.1(17) . . . . ? C9A C4A C5A C10 172(2) . . . . ? N1 C4A C5A C10 -7(2) . . . . ? C4A C5A C6A C7A 2.5(16) . . . . ? C10 C5A C6A C7A -172.5(9) . . . . ? C5A C6A C7A C8A -0.2(13) . . . . ? C6A C7A C8A C9A -0.5(12) . . . . ? C5A C4A C9A C13 174.2(14) . . . . ? N1 C4A C9A C13 -7(3) . . . . ? C5A C4A C9A C8A 4(3) . . . . ? N1 C4A C9A C8A -177.6(13) . . . . ? C7A C8A C9A C13 -172.9(9) . . . . ? C7A C8A C9A C4A -1(2) . . . . ? C1 N1 C4B C5B 95.5(18) . . . . ? C2 N1 C4B C5B -82.7(18) . . . . ? C4A N1 C4B C5B -146(27) . . . . ? C1 N1 C4B C9B -94(2) . . . . ? C2 N1 C4B C9B 88(2) . . . . ? C4A N1 C4B C9B 24(23) . . . . ? C9B C4B C5B C10 -174.7(19) . . . . ? N1 C4B C5B C10 -5(3) . . . . ? C9B C4B C5B C6B 5(3) . . . . ? N1 C4B C5B C6B 174.5(15) . . . . ? C10 C5B C6B C7B 177.1(8) . . . . ? C4B C5B C6B C7B -2.5(17) . . . . ? C5B C6B C7B C8B 0.9(12) . . . . ? C6B C7B C8B C9B -1.2(13) . . . . ? C5B C4B C9B C8B -5(3) . . . . ? N1 C4B C9B C8B -174.0(16) . . . . ? C5B C4B C9B C13 -177.5(16) . . . . ? N1 C4B C9B C13 13(3) . . . . ? C7B C8B C9B C4B 3(2) . . . . ? C7B C8B C9B C13 175.0(10) . . . . ? C4B C5B C10 C12A -125.3(17) . . . . ? C6B C5B C10 C12A 55.2(10) . . . . ? C4B C5B C10 C11B 124.1(18) . . . . ? C6B C5B C10 C11B -55.5(13) . . . . ? C4B C5B C10 C11A 120.1(17) . . . . ? C6B C5B C10 C11A -59.4(9) . . . . ? C4B C5B C10 C12B -98.1(17) . . . . ? C6B C5B C10 C12B 82.4(9) . . . . ? C4B C5B C10 C5A 156(8) . . . . ? C6B C5B C10 C5A -23(6) . . . . ? C6A C5A C10 C5B 154(8) . . . . ? C4A C5A C10 C5B -21(7) . . . . ? C6A C5A C10 C12A 50.9(13) . . . . ? C4A C5A C10 C12A -124.2(13) . . . . ? C6A C5A C10 C11B -54.7(14) . . . . ? C4A C5A C10 C11B 130.2(14) . . . . ? C6A C5A C10 C11A -61.0(12) . . . . ? C4A C5A C10 C11A 123.9(13) . . . . ? C6A C5A C10 C12B 76.2(12) . . . . ? C4A C5A C10 C12B -98.9(14) . . . . ? C4A C9A C13 C14A 141(2) . . . . ? C8A C9A C13 C14A -47.6(11) . . . . ? C4A C9A C13 C15B -116(2) . . . . ? C8A C9A C13 C15B 54.6(13) . . . . ? C4A C9A C13 C15A -98(2) . . . . ? C8A C9A C13 C15A 73.3(10) . . . . ? C4A C9A C13 C9B -77(9) . . . . ? C8A C9A C13 C9B 94(9) . . . . ? C4A C9A C13 C14B 117(2) . . . . ? C8A C9A C13 C14B -71.9(11) . . . . ? C4B C9B C13 C9A 89(9) . . . . ? C8B C9B C13 C9A -83(9) . . . . ? C4B C9B C13 C14A 128.3(18) . . . . ? C8B C9B C13 C14A -43.3(14) . . . . ? C4B C9B C13 C15B -128.3(18) . . . . ? C8B C9B C13 C15B 60.1(14) . . . . ? C4B C9B C13 C15A -111.6(18) . . . . ? C8B C9B C13 C15A 76.8(12) . . . . ? C4B C9B C13 C14B 103.5(18) . . . . ? C8B C9B C13 C14B -68.2(13) . . . . ? C1 N2 C16 C21 -55.7(4) . . . . ? C3 N2 C16 C21 102.2(3) . . . . ? C1 N2 C16 C17 128.3(3) . . . . ? C3 N2 C16 C17 -73.8(3) . . . . ? C21 C16 C17 C18 -0.4(4) . . . . ? N2 C16 C17 C18 175.5(2) . . . . ? C21 C16 C17 C22 -178.6(3) . . . . ? N2 C16 C17 C22 -2.7(4) . . . . ? C16 C17 C18 C19 0.1(4) . . . . ? C22 C17 C18 C19 178.4(3) . . . . ? C17 C18 C19 C20 0.1(5) . . . . ? C18 C19 C20 C21 0.0(5) . . . . ? C19 C20 C21 C16 -0.3(5) . . . . ? C19 C20 C21 C25 -178.3(3) . . . . ? C17 C16 C21 C20 0.5(4) . . . . ? N2 C16 C21 C20 -175.3(3) . . . . ? C17 C16 C21 C25 178.4(3) . . . . ? N2 C16 C21 C25 2.6(4) . . . . ? C18 C17 C22 C24 -68.4(3) . . . . ? C16 C17 C22 C24 109.7(3) . . . . ? C18 C17 C22 C23 54.4(4) . . . . ? C16 C17 C22 C23 -127.4(3) . . . . ? C20 C21 C25 C27B -37.0(8) . . . . ? C16 C21 C25 C27B 145.2(8) . . . . ? C20 C21 C25 C26B 94.9(6) . . . . ? C16 C21 C25 C26B -82.9(6) . . . . ? C20 C21 C25 C27A -50.2(7) . . . . ? C16 C21 C25 C27A 131.9(7) . . . . ? C20 C21 C25 C26A 66.5(6) . . . . ? C16 C21 C25 C26A -111.4(6) . . . . ? O1 C28 C29 C30 175.2(2) . . . . ? C33 C28 C29 C30 -6.1(4) . . . . ? O1 C28 C29 C34 -5.1(4) . . . . ? C33 C28 C29 C34 173.6(3) . . . . ? C28 C29 C30 C31 3.1(4) . . . . ? C34 C29 C30 C31 -176.6(3) . . . . ? C29 C30 C31 C32 1.0(4) . . . . ? C29 C30 C31 C38 -178.9(3) . . . . ? C30 C31 C32 C33 -1.9(4) . . . . ? C38 C31 C32 C33 178.0(3) . . . . ? C31 C32 C33 C28 -1.3(4) . . . . ? C31 C32 C33 C39A -172.3(3) . . . . ? C31 C32 C33 C39B 158.0(4) . . . . ? O1 C28 C33 C32 -176.0(3) . . . . ? C29 C28 C33 C32 5.2(4) . . . . ? O1 C28 C33 C39A -4.9(5) . . . . ? C29 C28 C33 C39A 176.4(3) . . . . ? O1 C28 C33 C39B 25.3(5) . . . . ? C29 C28 C33 C39B -153.5(4) . . . . ? C30 C29 C34 C37 120.9(3) . . . . ? C28 C29 C34 C37 -58.9(3) . . . . ? C30 C29 C34 C36 -118.4(3) . . . . ? C28 C29 C34 C36 61.8(3) . . . . ? C30 C29 C34 C35 1.2(4) . . . . ? C28 C29 C34 C35 -178.6(3) . . . . ? C32 C33 C39A C42A -7.4(5) . . . . ? C28 C33 C39A C42A -178.4(3) . . . . ? C39B C33 C39A C42A 81.5(5) . . . . ? C32 C33 C39A C40A -127.4(4) . . . . ? C28 C33 C39A C40A 61.6(5) . . . . ? C39B C33 C39A C40A -38.4(5) . . . . ? C32 C33 C39A C41A 109.8(4) . . . . ? C28 C33 C39A C41A -61.1(5) . . . . ? C39B C33 C39A C41A -161.2(7) . . . . ? C32 C33 C39B C40B -117.1(2) . . . . ? C28 C33 C39B C40B 42.0(3) . . . . ? C39A C33 C39B C40B 137.0(5) . . . . ? C32 C33 C39B C42B 12.4(6) . . . . ? C28 C33 C39B C42B 171.5(5) . . . . ? C39A C33 C39B C42B -93.4(7) . . . . ? C32 C33 C39B C41B 120.1(6) . . . . ? C28 C33 C39B C41B -80.8(6) . . . . ? C39A C33 C39B C41B 14.3(7) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A C1 H1 O1 1.00(3) 1.89(3) 2.886(3) 175(2) 3_645 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 26.50 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.204 _refine_diff_density_min -0.158 _refine_diff_density_rms 0.032 #============================================================================== # End of CIF #==============================================================================