# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2007 data_global _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 _journal_year ? _journal_volume ? _journal_page_first ? _publ_section_title ;Capturing a [c2]Daisy Chain Using the Threading-Followed-by-Swelling Approach ; _publ_contact_author_name 'Prof. Sheng-Hsien Chiu' _publ_contact_author_email SHCHIU@NTU.EDU.TW loop_ _publ_author_name 'Sheng-Hsien Chiu' 'Sheng-Yao Hsesh' 'Chien-Chen Lai' 'Yi-Hung Liu' ; Shie-Ming Peng ; 'Shau-Hua Ueng' data_ic12639 _database_code_depnum_ccdc_archive 'CCDC 664527' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C50 H53 Cl12 F6 N2 O4 P' _chemical_formula_weight 1316.31 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' F F 0.0171 0.0103 '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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 12.8645(4) _cell_length_b 13.4307(3) _cell_length_c 18.2973(5) _cell_angle_alpha 94.368(2) _cell_angle_beta 102.7600(10) _cell_angle_gamma 100.435(2) _cell_volume 3010.00(14) _cell_formula_units_Z 2 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 27649 _cell_measurement_theta_min 1 _cell_measurement_theta_max 27.5 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.452 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1344 _exptl_absorpt_coefficient_mu 0.640 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.901 _exptl_absorpt_correction_T_max 0.962 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(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 'Nonius KappaCCD' _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 21038 _diffrn_reflns_av_R_equivalents 0.0690 _diffrn_reflns_av_sigmaI/netI 0.1181 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 1.55 _diffrn_reflns_theta_max 27.48 _reflns_number_total 13743 _reflns_number_gt 5262 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Nonius BV)' _computing_cell_refinement 'HKL Denzo & Scalepack (Otwinowski & Minor)' _computing_data_reduction 'HKL Denzo & Scalepack (Otwinowski & Minor)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXTL _computing_publication_material 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. Because of the large correlation between thermal parameters, the restraint was necessary for convergence of the refinement process. In large supermolecular structure with poor data to parameter ratios, they often are needed with geometrical and anisotropic displacement parameters restraints. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+3.4846P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 13743 _refine_ls_number_parameters 704 _refine_ls_number_restraints 246 _refine_ls_R_factor_all 0.2352 _refine_ls_R_factor_gt 0.1094 _refine_ls_wR_factor_ref 0.3256 _refine_ls_wR_factor_gt 0.2561 _refine_ls_goodness_of_fit_ref 1.098 _refine_ls_restrained_S_all 1.137 _refine_ls_shift/su_max 0.089 _refine_ls_shift/su_mean 0.005 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.7752(3) 0.6618(3) 0.5601(2) 0.0650(11) Uani 1 1 d . . . O2 O 1.0441(3) 0.8687(3) 0.7647(2) 0.0622(10) Uani 1 1 d . . . O3 O 0.7755(4) 0.9058(4) 1.0083(3) 0.0875(14) Uani 1 1 d . . . O4 O 0.3980(3) 0.5587(4) 0.7253(3) 0.0845(14) Uani 1 1 d . . . N1 N 0.9830(3) 0.7803(3) 0.6149(3) 0.0562(11) Uani 1 1 d . . . N2 N 1.1824(3) 1.2230(3) 0.2918(2) 0.0482(10) Uani 1 1 d . . . H2A H 1.1923 1.2591 0.3371 0.058 Uiso 1 1 calc R . . H2B H 1.1110 1.1956 0.2751 0.058 Uiso 1 1 calc R . . C1 C 0.8491(6) 0.6696(5) 0.5126(4) 0.085(2) Uani 1 1 d . . . H1B H 0.8108 0.6775 0.4621 0.102 Uiso 1 1 calc R . . H1C H 0.8763 0.6070 0.5097 0.102 Uiso 1 1 calc R . . C2 C 0.9437(4) 0.7583(4) 0.5406(3) 0.0572(14) Uani 1 1 d . . . C3 C 0.9867(4) 0.8105(4) 0.4878(3) 0.0586(15) Uani 1 1 d . . . H3A H 0.9546 0.7926 0.4366 0.070 Uiso 1 1 calc R . . C4 C 1.0770(4) 0.8889(4) 0.5111(3) 0.0482(12) Uani 1 1 d . . . C5 C 1.1187(4) 0.9109(4) 0.5881(3) 0.0583(14) Uani 1 1 d . . . H5A H 1.1794 0.9630 0.6070 0.070 Uiso 1 1 calc R . . C6 C 1.0713(4) 0.8566(4) 0.6374(3) 0.0556(14) Uani 1 1 d . . . C7 C 1.1225(5) 0.8797(5) 0.7201(3) 0.0761(19) Uani 1 1 d . . . H7A H 1.1722 0.8342 0.7344 0.091 Uiso 1 1 calc R . . H7B H 1.1646 0.9490 0.7306 0.091 Uiso 1 1 calc R . . C8 C 1.0967(5) 0.8917(6) 0.8427(3) 0.085(2) Uani 1 1 d . . . H8A H 1.1454 0.9579 0.8518 0.102 Uiso 1 1 calc R . . H8B H 1.1395 0.8410 0.8581 0.102 Uiso 1 1 calc R . . C9 C 1.0122(5) 0.8920(5) 0.8874(3) 0.0667(17) Uani 1 1 d . . . C10 C 0.9866(5) 0.8136(5) 0.9297(4) 0.0727(18) Uani 1 1 d . . . H10A H 1.0232 0.7598 0.9315 0.087 Uiso 1 1 calc R . . C11 C 0.9058(6) 0.8156(5) 0.9695(3) 0.0729(18) Uani 1 1 d . . . H11A H 0.8886 0.7628 0.9976 0.087 Uiso 1 1 calc R . . C12 C 0.8518(5) 0.8945(5) 0.9675(3) 0.0670(17) Uani 1 1 d . . . C13 C 0.8776(6) 0.9725(5) 0.9262(4) 0.0723(17) Uani 1 1 d . . . H13A H 0.8420 1.0269 0.9251 0.087 Uiso 1 1 calc R . . C14 C 0.9559(6) 0.9699(5) 0.8868(3) 0.0760(19) Uani 1 1 d . . . H14A H 0.9717 1.0228 0.8584 0.091 Uiso 1 1 calc R . . C15 C 0.7246(6) 0.8158(6) 1.0345(4) 0.093(2) Uani 1 1 d . . . H15A H 0.6813 0.8349 1.0684 0.112 Uiso 1 1 calc R . . H15B H 0.7805 0.7843 1.0627 0.112 Uiso 1 1 calc R . . C16 C 0.6524(5) 0.7392(5) 0.9705(4) 0.0720(17) Uani 1 1 d . . . C17 C 0.6022(5) 0.7685(5) 0.9043(4) 0.0731(17) Uani 1 1 d . . . H17A H 0.6165 0.8371 0.8973 0.088 Uiso 1 1 calc R . . C18 C 0.5310(5) 0.7000(5) 0.8473(4) 0.0719(17) Uani 1 1 d . . . H18A H 0.4980 0.7229 0.8029 0.086 Uiso 1 1 calc R . . C19 C 0.5083(5) 0.5969(5) 0.8558(4) 0.0734(18) Uani 1 1 d . . . C20 C 0.5610(6) 0.5677(6) 0.9220(5) 0.089(2) Uani 1 1 d . . . H20A H 0.5486 0.4990 0.9288 0.107 Uiso 1 1 calc R . . C21 C 0.6315(6) 0.6368(6) 0.9784(4) 0.090(2) Uani 1 1 d . . . H21A H 0.6657 0.6142 1.0225 0.108 Uiso 1 1 calc R . . C22 C 0.4244(6) 0.5211(6) 0.7965(4) 0.091(2) Uani 1 1 d . . . H22A H 0.4519 0.4592 0.7898 0.109 Uiso 1 1 calc R . . H22B H 0.3586 0.5036 0.8143 0.109 Uiso 1 1 calc R . . C23 C 0.4703(5) 0.5589(5) 0.6801(4) 0.0678(17) Uani 1 1 d . . . C24 C 0.5378(6) 0.4915(5) 0.6787(4) 0.0762(19) Uani 1 1 d . . . H24A H 0.5378 0.4410 0.7107 0.091 Uiso 1 1 calc R . . C25 C 0.6066(5) 0.4980(5) 0.6294(4) 0.0744(18) Uani 1 1 d . . . H25A H 0.6524 0.4518 0.6292 0.089 Uiso 1 1 calc R . . C26 C 0.6081(5) 0.5720(5) 0.5806(3) 0.0683(17) Uani 1 1 d . . . C27 C 0.5379(6) 0.6373(5) 0.5817(4) 0.080(2) Uani 1 1 d . . . H27A H 0.5351 0.6857 0.5479 0.096 Uiso 1 1 calc R . . C28 C 0.4706(5) 0.6334(5) 0.6320(4) 0.0788(19) Uani 1 1 d . . . H28A H 0.4262 0.6807 0.6332 0.095 Uiso 1 1 calc R . . C29 C 0.6835(5) 0.5796(5) 0.5288(4) 0.088(2) Uani 1 1 d . . . H29A H 0.7082 0.5161 0.5231 0.105 Uiso 1 1 calc R . . H29B H 0.6458 0.5924 0.4795 0.105 Uiso 1 1 calc R . . C30 C 1.1241(4) 0.9493(4) 0.4571(3) 0.0484(12) Uani 1 1 d . . . C31 C 1.2103(5) 1.0310(4) 0.4812(3) 0.0743(19) Uani 1 1 d . . . H31A H 1.2415 1.0473 0.5327 0.089 Uiso 1 1 calc R . . C32 C 1.2518(5) 1.0897(5) 0.4312(3) 0.0739(18) Uani 1 1 d . . . H32A H 1.3104 1.1440 0.4497 0.089 Uiso 1 1 calc R . . C33 C 1.2082(4) 1.0691(4) 0.3555(3) 0.0528(13) Uani 1 1 d . . . C34 C 1.1242(5) 0.9859(5) 0.3301(3) 0.0733(18) Uani 1 1 d . . . H34A H 1.0942 0.9690 0.2785 0.088 Uiso 1 1 calc R . . C35 C 1.0841(5) 0.9274(5) 0.3804(3) 0.0710(18) Uani 1 1 d . . . H35A H 1.0280 0.8710 0.3617 0.085 Uiso 1 1 calc R . . C36 C 1.2446(5) 1.1396(4) 0.3006(3) 0.0579(14) Uani 1 1 d U . . H36A H 1.3216 1.1689 0.3188 0.069 Uiso 1 1 calc R . . H36B H 1.2339 1.1004 0.2518 0.069 Uiso 1 1 calc R . . C37 C 1.2167(4) 1.2930(4) 0.2380(3) 0.0569(13) Uani 1 1 d U . . H37A H 1.2081 1.2542 0.1894 0.068 Uiso 1 1 calc R . . H37B H 1.2929 1.3250 0.2568 0.068 Uiso 1 1 calc R . . C38 C 1.1490(5) 1.3741(4) 0.2288(4) 0.0689(15) Uani 1 1 d U . . H38A H 1.1564 1.4119 0.2777 0.083 Uiso 1 1 calc R . . H38B H 1.0729 1.3421 0.2092 0.083 Uiso 1 1 calc R . . C39 C 1.1855(6) 1.4477(5) 0.1748(4) 0.0872(17) Uani 1 1 d U . . H39A H 1.2627 1.4759 0.1932 0.105 Uiso 1 1 calc R . . H39B H 1.1747 1.4098 0.1255 0.105 Uiso 1 1 calc R . . C40 C 1.1246(7) 1.5348(6) 0.1663(5) 0.1066(19) Uani 1 1 d U . . H40A H 1.1197 1.5612 0.2167 0.128 Uiso 1 1 calc R . . C41 C 1.1813(8) 1.6195(7) 0.1334(6) 0.131(2) Uani 1 1 d U . . H41A H 1.2573 1.6344 0.1603 0.157 Uiso 1 1 calc R . . H41B H 1.1781 1.5950 0.0815 0.157 Uiso 1 1 calc R . . C42 C 1.1434(10) 1.7152(8) 0.1330(7) 0.150(3) Uani 1 1 d U . . H42A H 1.1831 1.7684 0.1146 0.180 Uiso 1 1 calc R . . C43 C 1.0542(11) 1.7346(9) 0.1575(7) 0.156(3) Uani 1 1 d U . . H43A H 1.0572 1.8011 0.1776 0.187 Uiso 1 1 calc R . . C44 C 0.9627(10) 1.6651(9) 0.1547(7) 0.153(3) Uani 1 1 d U . . H44A H 0.9026 1.6970 0.1339 0.183 Uiso 1 1 calc R . . H44B H 0.9605 1.6586 0.2068 0.183 Uiso 1 1 calc R . . C45 C 0.9354(10) 1.5639(8) 0.1171(7) 0.150(3) Uani 1 1 d U . . H45A H 0.8638 1.5380 0.0905 0.180 Uiso 1 1 calc R . . C46 C 1.0121(8) 1.5013(7) 0.1183(6) 0.125(2) Uani 1 1 d U . . H46A H 0.9923 1.4383 0.0888 0.150 Uiso 1 1 calc R . . P1 P 0.72280(16) 0.77414(14) 0.26982(12) 0.0849(6) Uani 1 1 d . . . F1 F 0.8419(4) 0.8070(7) 0.2788(7) 0.278(6) Uani 1 1 d . . . F2 F 0.5958(5) 0.7398(5) 0.2566(4) 0.175(3) Uani 1 1 d . . . F3 F 0.7116(4) 0.7041(4) 0.1942(3) 0.1326(18) Uani 1 1 d . . . F4 F 0.7045(7) 0.8633(4) 0.2249(4) 0.194(3) Uani 1 1 d . . . F5 F 0.7334(8) 0.8458(5) 0.3399(4) 0.228(4) Uani 1 1 d . . . F6 F 0.7296(9) 0.6818(5) 0.3106(4) 0.238(5) Uani 1 1 d . . . C47 C 0.8621(7) 0.4695(7) 0.3396(5) 0.118(3) Uani 1 1 d . . . H47A H 0.8072 0.5121 0.3315 0.141 Uiso 1 1 calc R . . Cl1 Cl 0.8496(3) 0.3951(3) 0.25585(16) 0.1572(11) Uani 1 1 d . . . Cl2 Cl 0.9895(2) 0.5489(3) 0.3690(2) 0.1661(12) Uani 1 1 d . . . Cl3 Cl 0.8388(2) 0.3929(2) 0.41063(15) 0.1309(9) Uani 1 1 d . . . C49 C 0.5246(7) 0.9962(7) 0.2410(6) 0.128(3) Uani 1 1 d . . . H49A H 0.5497 0.9328 0.2511 0.154 Uiso 1 1 calc R . . Cl7 Cl 0.3828(2) 0.9679(3) 0.2148(2) 0.1626(12) Uani 1 1 d . . . Cl8 Cl 0.5752(2) 1.0424(3) 0.1654(2) 0.1767(14) Uani 1 1 d . . . Cl9 Cl 0.5696(4) 1.0793(4) 0.3211(3) 0.264(3) Uani 1 1 d . . . C50 C 0.3831(7) 0.7693(10) -0.0059(6) 0.144(4) Uani 1 1 d . . . H50A H 0.4390 0.7768 -0.0350 0.173 Uiso 1 1 calc R . . Cl10 Cl 0.2797(3) 0.6704(3) -0.0522(2) 0.1916(16) Uani 1 1 d . . . Cl11 Cl 0.3354(3) 0.8858(3) -0.00221(16) 0.1555(11) Uani 1 1 d . . . Cl12 Cl 0.4438(2) 0.7476(2) 0.08417(15) 0.1294(9) Uani 1 1 d . . . C48 C 0.3467(10) 0.8222(10) 0.4088(8) 0.160(3) Uani 0.553(5) 1 d PU A 1 H48A H 0.3374 0.8931 0.4122 0.192 Uiso 0.553(5) 1 calc PR A 1 Cl4 Cl 0.4770(8) 0.8136(9) 0.4060(6) 0.192(4) Uani 0.553(5) 1 d PU A 1 Cl5 Cl 0.3081(7) 0.7605(7) 0.4805(4) 0.171(3) Uani 0.553(5) 1 d PU A 1 Cl6 Cl 0.2638(7) 0.7490(5) 0.3242(5) 0.211(3) Uani 0.553(5) 1 d PU A 1 C48' C 0.3467(10) 0.8222(10) 0.4088(8) 0.160(3) Uani 0.447(5) 1 d PU A 2 H48B H 0.3133 0.8721 0.3806 0.192 Uiso 0.447(5) 1 calc PR A 2 Cl4' Cl 0.2489(8) 0.7201(6) 0.4167(7) 0.180(3) Uani 0.447(5) 1 d PU A 2 Cl5' Cl 0.4173(9) 0.8770(9) 0.4997(6) 0.224(4) Uani 0.447(5) 1 d PU A 2 Cl6' Cl 0.4414(10) 0.7799(8) 0.3652(7) 0.165(3) Uani 0.447(5) 1 d PU A 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 O1 0.067(2) 0.062(2) 0.055(2) -0.0083(18) 0.019(2) -0.0161(19) O2 0.056(2) 0.079(3) 0.043(2) 0.0025(19) 0.0080(18) -0.0034(19) O3 0.083(3) 0.097(3) 0.073(3) -0.017(3) 0.024(3) -0.001(3) O4 0.063(3) 0.099(3) 0.083(3) -0.004(3) 0.026(3) -0.010(2) N1 0.051(3) 0.062(3) 0.052(3) 0.001(2) 0.016(2) -0.001(2) N2 0.047(2) 0.046(2) 0.050(3) 0.006(2) 0.012(2) 0.0052(19) C1 0.098(5) 0.084(4) 0.058(4) -0.012(3) 0.034(4) -0.029(4) C2 0.059(3) 0.057(3) 0.052(3) -0.001(3) 0.019(3) -0.002(3) C3 0.063(3) 0.061(3) 0.045(3) -0.004(3) 0.013(3) -0.002(3) C4 0.052(3) 0.048(3) 0.047(3) 0.005(2) 0.015(3) 0.011(2) C5 0.053(3) 0.060(3) 0.054(4) 0.006(3) 0.008(3) -0.001(3) C6 0.050(3) 0.067(3) 0.047(3) 0.005(3) 0.013(3) 0.005(3) C7 0.055(4) 0.111(5) 0.052(4) 0.013(3) 0.013(3) -0.010(3) C8 0.063(4) 0.130(6) 0.048(4) 0.004(4) 0.007(3) -0.008(4) C9 0.059(4) 0.085(4) 0.041(3) -0.006(3) 0.000(3) -0.001(3) C10 0.079(4) 0.069(4) 0.060(4) -0.001(3) 0.005(4) 0.008(3) C11 0.079(4) 0.075(4) 0.053(4) 0.004(3) 0.014(3) -0.010(4) C12 0.061(4) 0.078(4) 0.049(4) -0.016(3) 0.010(3) -0.003(3) C13 0.077(4) 0.066(4) 0.062(4) -0.005(3) 0.003(4) 0.008(3) C14 0.079(5) 0.082(5) 0.047(4) 0.006(3) -0.005(3) -0.010(4) C15 0.082(5) 0.126(6) 0.064(4) 0.003(4) 0.026(4) -0.004(4) C16 0.065(4) 0.088(5) 0.063(4) 0.009(4) 0.023(3) 0.007(3) C17 0.080(4) 0.068(4) 0.064(4) 0.005(3) 0.013(4) 0.002(3) C18 0.075(4) 0.074(4) 0.065(4) 0.013(3) 0.015(3) 0.011(3) C19 0.076(4) 0.071(4) 0.077(5) 0.010(4) 0.035(4) 0.002(3) C20 0.101(6) 0.078(5) 0.098(6) 0.030(5) 0.047(5) 0.009(4) C21 0.092(5) 0.101(6) 0.074(5) 0.022(4) 0.014(4) 0.015(5) C22 0.087(5) 0.089(5) 0.089(5) -0.003(4) 0.038(4) -0.016(4) C23 0.055(4) 0.069(4) 0.064(4) -0.008(3) 0.009(3) -0.014(3) C24 0.076(4) 0.068(4) 0.078(5) 0.007(3) 0.024(4) -0.007(4) C25 0.069(4) 0.061(4) 0.086(5) -0.006(4) 0.022(4) -0.001(3) C26 0.058(4) 0.069(4) 0.061(4) -0.008(3) 0.007(3) -0.016(3) C27 0.070(4) 0.078(5) 0.074(5) 0.017(4) 0.000(4) -0.017(4) C28 0.056(4) 0.075(4) 0.102(5) 0.009(4) 0.020(4) 0.005(3) C29 0.083(5) 0.085(4) 0.076(5) -0.022(4) 0.027(4) -0.030(4) C30 0.045(3) 0.047(3) 0.053(3) 0.007(2) 0.011(3) 0.010(2) C31 0.090(5) 0.070(4) 0.046(3) 0.007(3) 0.004(3) -0.011(3) C32 0.073(4) 0.075(4) 0.057(4) 0.015(3) 0.004(3) -0.019(3) C33 0.056(3) 0.051(3) 0.055(3) 0.009(3) 0.016(3) 0.013(3) C34 0.086(4) 0.073(4) 0.049(3) 0.011(3) 0.009(3) -0.007(3) C35 0.073(4) 0.066(4) 0.058(4) 0.007(3) 0.005(3) -0.015(3) C36 0.059(3) 0.060(3) 0.056(3) 0.013(3) 0.016(3) 0.009(3) C37 0.055(3) 0.055(3) 0.061(3) 0.015(2) 0.017(3) 0.006(2) C38 0.068(3) 0.065(3) 0.078(4) 0.022(3) 0.020(3) 0.016(3) C39 0.087(3) 0.074(3) 0.107(4) 0.040(3) 0.026(3) 0.017(3) C40 0.110(4) 0.083(3) 0.132(4) 0.048(3) 0.022(4) 0.026(3) C41 0.135(4) 0.098(4) 0.161(5) 0.049(4) 0.022(4) 0.027(4) C42 0.153(5) 0.111(4) 0.181(5) 0.051(5) 0.020(5) 0.024(5) C43 0.165(6) 0.114(5) 0.187(6) 0.030(5) 0.015(5) 0.053(5) C44 0.151(5) 0.139(5) 0.181(6) 0.042(5) 0.034(5) 0.057(5) C45 0.140(5) 0.129(5) 0.179(5) 0.051(5) 0.017(5) 0.034(5) C46 0.121(4) 0.099(4) 0.158(5) 0.045(4) 0.017(4) 0.040(4) P1 0.0855(14) 0.0673(11) 0.0827(13) -0.0021(10) -0.0065(10) 0.0034(9) F1 0.064(3) 0.264(9) 0.431(14) -0.130(9) -0.002(6) -0.010(4) F2 0.120(4) 0.161(5) 0.232(7) -0.041(5) 0.069(5) -0.009(4) F3 0.151(4) 0.113(3) 0.120(4) -0.021(3) 0.049(3) -0.012(3) F4 0.283(9) 0.103(4) 0.186(6) 0.039(4) 0.035(6) 0.029(5) F5 0.347(11) 0.162(6) 0.126(5) -0.085(4) 0.058(6) -0.035(6) F6 0.388(12) 0.119(5) 0.147(6) 0.039(4) -0.060(7) 0.042(6) C47 0.111(7) 0.139(7) 0.100(6) -0.006(6) 0.023(5) 0.026(6) Cl1 0.176(3) 0.199(3) 0.1098(19) -0.0093(19) 0.0515(19) 0.064(2) Cl2 0.135(2) 0.173(3) 0.180(3) 0.013(2) 0.043(2) 0.003(2) Cl3 0.1325(19) 0.157(2) 0.1228(19) 0.0285(17) 0.0539(16) 0.0468(17) C49 0.085(6) 0.101(6) 0.196(11) 0.012(7) 0.018(6) 0.034(5) Cl7 0.1022(18) 0.188(3) 0.194(3) -0.023(2) 0.0326(19) 0.0428(18) Cl8 0.128(2) 0.180(3) 0.229(4) 0.101(3) 0.027(2) 0.037(2) Cl9 0.241(5) 0.225(4) 0.257(5) -0.108(4) -0.073(4) 0.088(4) C50 0.079(6) 0.244(12) 0.113(7) -0.023(8) 0.032(5) 0.049(7) Cl10 0.148(3) 0.236(4) 0.149(3) -0.069(3) -0.006(2) 0.022(2) Cl11 0.145(2) 0.194(3) 0.121(2) 0.031(2) 0.0052(18) 0.047(2) Cl12 0.1097(17) 0.160(2) 0.1153(19) 0.0052(16) 0.0107(14) 0.0423(15) C48 0.172(5) 0.161(5) 0.176(5) 0.040(5) 0.054(5) 0.082(4) Cl4 0.143(5) 0.226(8) 0.201(8) 0.070(6) 0.021(5) 0.033(5) Cl5 0.195(6) 0.213(6) 0.162(5) 0.091(5) 0.087(5) 0.107(5) Cl6 0.239(6) 0.166(5) 0.187(6) -0.019(4) -0.032(5) 0.059(5) C48' 0.172(5) 0.161(5) 0.176(5) 0.040(5) 0.054(5) 0.082(4) Cl4' 0.178(6) 0.147(5) 0.256(8) 0.053(6) 0.107(6) 0.057(5) Cl5' 0.222(7) 0.245(8) 0.200(7) -0.015(6) -0.004(6) 0.115(6) Cl6' 0.203(8) 0.136(5) 0.200(8) 0.037(5) 0.119(6) 0.054(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 O1 C1 1.418(7) . ? O1 C29 1.439(6) . ? O2 C8 1.423(7) . ? O2 C7 1.425(7) . ? O3 C12 1.380(7) . ? O3 C15 1.435(8) . ? O4 C23 1.374(8) . ? O4 C22 1.426(8) . ? N1 C2 1.331(7) . ? N1 C6 1.348(7) . ? N2 C36 1.489(7) . ? N2 C37 1.493(6) . ? N2 H2A 0.9000 . ? N2 H2B 0.9000 . ? C1 C2 1.507(8) . ? C1 H1B 0.9700 . ? C1 H1C 0.9700 . ? C2 C3 1.388(7) . ? C3 C4 1.382(7) . ? C3 H3A 0.9300 . ? C4 C5 1.381(7) . ? C4 C30 1.487(7) . ? C5 C6 1.379(7) . ? C5 H5A 0.9300 . ? C6 C7 1.495(8) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C9 1.497(9) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 C14 1.376(9) . ? C9 C10 1.388(9) . ? C10 C11 1.398(9) . ? C10 H10A 0.9300 . ? C11 C12 1.368(9) . ? C11 H11A 0.9300 . ? C12 C13 1.372(9) . ? C13 C14 1.366(9) . ? C13 H13A 0.9300 . ? C14 H14A 0.9300 . ? C15 C16 1.511(9) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 C17 1.364(9) . ? C16 C21 1.377(9) . ? C17 C18 1.378(8) . ? C17 H17A 0.9300 . ? C18 C19 1.390(9) . ? C18 H18A 0.9300 . ? C19 C20 1.374(10) . ? C19 C22 1.515(9) . ? C20 C21 1.372(10) . ? C20 H20A 0.9300 . ? C21 H21A 0.9300 . ? C22 H22A 0.9700 . ? C22 H22B 0.9700 . ? C23 C24 1.366(9) . ? C23 C28 1.382(9) . ? C24 C25 1.392(9) . ? C24 H24A 0.9300 . ? C25 C26 1.386(9) . ? C25 H25A 0.9300 . ? C26 C27 1.370(9) . ? C26 C29 1.494(9) . ? C27 C28 1.394(10) . ? C27 H27A 0.9300 . ? C28 H28A 0.9300 . ? C29 H29A 0.9700 . ? C29 H29B 0.9700 . ? C30 C35 1.372(7) . ? C30 C31 1.377(7) . ? C31 C32 1.384(8) . ? C31 H31A 0.9300 . ? C32 C33 1.361(8) . ? C32 H32A 0.9300 . ? C33 C34 1.376(8) . ? C33 C36 1.522(7) . ? C34 C35 1.381(8) . ? C34 H34A 0.9300 . ? C35 H35A 0.9300 . ? C36 H36A 0.9700 . ? C36 H36B 0.9700 . ? C37 C38 1.510(8) . ? C37 H37A 0.9700 . ? C37 H37B 0.9700 . ? C38 C39 1.537(8) . ? C38 H38A 0.9700 . ? C38 H38B 0.9700 . ? C39 C40 1.520(10) . ? C39 H39A 0.9700 . ? C39 H39B 0.9700 . ? C40 C41 1.479(11) . ? C40 C46 1.487(12) . ? C40 H40A 0.9800 . ? C41 C42 1.454(13) . ? C41 H41A 0.9700 . ? C41 H41B 0.9700 . ? C42 C43 1.380(15) . ? C42 H42A 0.9300 . ? C43 C44 1.352(15) . ? C43 H43A 0.9300 . ? C44 C45 1.423(14) . ? C44 H44A 0.9700 . ? C44 H44B 0.9700 . ? C45 C46 1.405(13) . ? C45 H45A 0.9300 . ? C46 H46A 0.9300 . ? P1 F1 1.484(6) . ? P1 F6 1.502(6) . ? P1 F5 1.509(6) . ? P1 F4 1.528(6) . ? P1 F2 1.574(6) . ? P1 F3 1.576(5) . ? C47 Cl1 1.724(9) . ? C47 Cl2 1.733(9) . ? C47 Cl3 1.762(10) . ? C47 H47A 0.9800 . ? C49 Cl9 1.695(10) . ? C49 Cl7 1.743(9) . ? C49 Cl8 1.762(11) . ? C49 H49A 0.9800 . ? C50 Cl10 1.716(11) . ? C50 Cl12 1.731(11) . ? C50 Cl11 1.783(12) . ? C50 H50A 0.9800 . ? C48 Cl4 1.712(15) . ? C48 Cl5 1.720(13) . ? C48 Cl6 1.777(15) . ? C48 H48A 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 O1 C29 110.1(4) . . ? C8 O2 C7 110.3(4) . . ? C12 O3 C15 116.9(6) . . ? C23 O4 C22 117.8(6) . . ? C2 N1 C6 115.8(4) . . ? C36 N2 C37 112.3(4) . . ? C36 N2 H2A 109.1 . . ? C37 N2 H2A 109.1 . . ? C36 N2 H2B 109.1 . . ? C37 N2 H2B 109.1 . . ? H2A N2 H2B 107.9 . . ? O1 C1 C2 112.2(5) . . ? O1 C1 H1B 109.2 . . ? C2 C1 H1B 109.2 . . ? O1 C1 H1C 109.2 . . ? C2 C1 H1C 109.2 . . ? H1B C1 H1C 107.9 . . ? N1 C2 C3 123.8(5) . . ? N1 C2 C1 117.7(5) . . ? C3 C2 C1 118.5(5) . . ? C4 C3 C2 120.3(5) . . ? C4 C3 H3A 119.9 . . ? C2 C3 H3A 119.9 . . ? C5 C4 C3 115.9(5) . . ? C5 C4 C30 121.6(5) . . ? C3 C4 C30 122.4(5) . . ? C6 C5 C4 120.8(5) . . ? C6 C5 H5A 119.6 . . ? C4 C5 H5A 119.6 . . ? N1 C6 C5 123.4(5) . . ? N1 C6 C7 117.8(5) . . ? C5 C6 C7 118.8(5) . . ? O2 C7 C6 112.4(4) . . ? O2 C7 H7A 109.1 . . ? C6 C7 H7A 109.1 . . ? O2 C7 H7B 109.1 . . ? C6 C7 H7B 109.1 . . ? H7A C7 H7B 107.9 . . ? O2 C8 C9 109.0(5) . . ? O2 C8 H8A 109.9 . . ? C9 C8 H8A 109.9 . . ? O2 C8 H8B 109.9 . . ? C9 C8 H8B 109.9 . . ? H8A C8 H8B 108.3 . . ? C14 C9 C10 117.6(6) . . ? C14 C9 C8 120.7(6) . . ? C10 C9 C8 121.6(7) . . ? C9 C10 C11 120.0(7) . . ? C9 C10 H10A 120.0 . . ? C11 C10 H10A 120.0 . . ? C12 C11 C10 120.5(6) . . ? C12 C11 H11A 119.8 . . ? C10 C11 H11A 119.8 . . ? C11 C12 C13 119.6(6) . . ? C11 C12 O3 124.5(6) . . ? C13 C12 O3 115.8(7) . . ? C14 C13 C12 119.8(7) . . ? C14 C13 H13A 120.1 . . ? C12 C13 H13A 120.1 . . ? C13 C14 C9 122.5(6) . . ? C13 C14 H14A 118.8 . . ? C9 C14 H14A 118.8 . . ? O3 C15 C16 112.3(5) . . ? O3 C15 H15A 109.1 . . ? C16 C15 H15A 109.1 . . ? O3 C15 H15B 109.1 . . ? C16 C15 H15B 109.1 . . ? H15A C15 H15B 107.9 . . ? C17 C16 C21 117.5(6) . . ? C17 C16 C15 121.8(6) . . ? C21 C16 C15 120.7(7) . . ? C16 C17 C18 122.2(6) . . ? C16 C17 H17A 118.9 . . ? C18 C17 H17A 118.9 . . ? C17 C18 C19 120.3(6) . . ? C17 C18 H18A 119.9 . . ? C19 C18 H18A 119.9 . . ? C20 C19 C18 117.1(6) . . ? C20 C19 C22 121.4(6) . . ? C18 C19 C22 121.4(7) . . ? C21 C20 C19 122.0(7) . . ? C21 C20 H20A 119.0 . . ? C19 C20 H20A 119.0 . . ? C20 C21 C16 120.9(7) . . ? C20 C21 H21A 119.6 . . ? C16 C21 H21A 119.6 . . ? O4 C22 C19 113.2(5) . . ? O4 C22 H22A 108.9 . . ? C19 C22 H22A 108.9 . . ? O4 C22 H22B 108.9 . . ? C19 C22 H22B 108.9 . . ? H22A C22 H22B 107.8 . . ? C24 C23 O4 125.4(6) . . ? C24 C23 C28 119.4(6) . . ? O4 C23 C28 115.3(7) . . ? C23 C24 C25 120.3(6) . . ? C23 C24 H24A 119.8 . . ? C25 C24 H24A 119.8 . . ? C26 C25 C24 121.3(7) . . ? C26 C25 H25A 119.4 . . ? C24 C25 H25A 119.4 . . ? C27 C26 C25 117.5(6) . . ? C27 C26 C29 121.5(7) . . ? C25 C26 C29 120.9(7) . . ? C26 C27 C28 121.9(6) . . ? C26 C27 H27A 119.1 . . ? C28 C27 H27A 119.1 . . ? C23 C28 C27 119.6(7) . . ? C23 C28 H28A 120.2 . . ? C27 C28 H28A 120.2 . . ? O1 C29 C26 109.0(5) . . ? O1 C29 H29A 109.9 . . ? C26 C29 H29A 109.9 . . ? O1 C29 H29B 109.9 . . ? C26 C29 H29B 109.9 . . ? H29A C29 H29B 108.3 . . ? C35 C30 C31 116.1(5) . . ? C35 C30 C4 122.0(5) . . ? C31 C30 C4 121.9(5) . . ? C30 C31 C32 122.0(5) . . ? C30 C31 H31A 119.0 . . ? C32 C31 H31A 119.0 . . ? C33 C32 C31 121.0(5) . . ? C33 C32 H32A 119.5 . . ? C31 C32 H32A 119.5 . . ? C32 C33 C34 117.9(5) . . ? C32 C33 C36 121.6(5) . . ? C34 C33 C36 120.4(5) . . ? C33 C34 C35 120.5(6) . . ? C33 C34 H34A 119.7 . . ? C35 C34 H34A 119.7 . . ? C30 C35 C34 122.4(5) . . ? C30 C35 H35A 118.8 . . ? C34 C35 H35A 118.8 . . ? N2 C36 C33 111.4(4) . . ? N2 C36 H36A 109.3 . . ? C33 C36 H36A 109.4 . . ? N2 C36 H36B 109.3 . . ? C33 C36 H36B 109.3 . . ? H36A C36 H36B 108.0 . . ? N2 C37 C38 110.4(4) . . ? N2 C37 H37A 109.6 . . ? C38 C37 H37A 109.6 . . ? N2 C37 H37B 109.6 . . ? C38 C37 H37B 109.6 . . ? H37A C37 H37B 108.1 . . ? C37 C38 C39 110.7(5) . . ? C37 C38 H38A 109.5 . . ? C39 C38 H38A 109.5 . . ? C37 C38 H38B 109.5 . . ? C39 C38 H38B 109.5 . . ? H38A C38 H38B 108.1 . . ? C40 C39 C38 113.4(6) . . ? C40 C39 H39A 108.9 . . ? C38 C39 H39A 108.9 . . ? C40 C39 H39B 108.9 . . ? C38 C39 H39B 108.9 . . ? H39A C39 H39B 107.7 . . ? C41 C40 C46 107.9(7) . . ? C41 C40 C39 112.1(7) . . ? C46 C40 C39 112.3(7) . . ? C41 C40 H40A 108.1 . . ? C46 C40 H40A 108.1 . . ? C39 C40 H40A 108.1 . . ? C42 C41 C40 118.9(9) . . ? C42 C41 H41A 107.6 . . ? C40 C41 H41A 107.6 . . ? C42 C41 H41B 107.6 . . ? C40 C41 H41B 107.6 . . ? H41A C41 H41B 107.0 . . ? C43 C42 C41 126.1(10) . . ? C43 C42 H42A 116.9 . . ? C41 C42 H42A 116.9 . . ? C44 C43 C42 125.5(12) . . ? C44 C43 H43A 117.3 . . ? C42 C43 H43A 117.2 . . ? C43 C44 C45 126.0(12) . . ? C43 C44 H44A 105.8 . . ? C45 C44 H44A 105.8 . . ? C43 C44 H44B 105.8 . . ? C45 C44 H44B 105.8 . . ? H44A C44 H44B 106.2 . . ? C46 C45 C44 122.7(11) . . ? C46 C45 H45A 118.7 . . ? C44 C45 H45A 118.6 . . ? C45 C46 C40 120.7(10) . . ? C45 C46 H46A 119.6 . . ? C40 C46 H46A 119.7 . . ? F1 P1 F6 95.7(6) . . ? F1 P1 F5 88.1(5) . . ? F6 P1 F5 94.8(5) . . ? F1 P1 F4 89.5(6) . . ? F6 P1 F4 174.5(5) . . ? F5 P1 F4 87.2(4) . . ? F1 P1 F2 177.6(6) . . ? F6 P1 F2 85.9(5) . . ? F5 P1 F2 93.6(5) . . ? F4 P1 F2 88.8(4) . . ? F1 P1 F3 91.5(4) . . ? F6 P1 F3 88.2(4) . . ? F5 P1 F3 177.0(4) . . ? F4 P1 F3 89.8(4) . . ? F2 P1 F3 86.7(3) . . ? Cl1 C47 Cl2 111.3(5) . . ? Cl1 C47 Cl3 110.7(5) . . ? Cl2 C47 Cl3 109.6(5) . . ? Cl1 C47 H47A 108.4 . . ? Cl2 C47 H47A 108.4 . . ? Cl3 C47 H47A 108.4 . . ? Cl9 C49 Cl7 110.6(6) . . ? Cl9 C49 Cl8 112.5(6) . . ? Cl7 C49 Cl8 109.4(6) . . ? Cl9 C49 H49A 108.1 . . ? Cl7 C49 H49A 108.1 . . ? Cl8 C49 H49A 108.1 . . ? Cl10 C50 Cl12 112.8(7) . . ? Cl10 C50 Cl11 110.6(5) . . ? Cl12 C50 Cl11 110.1(5) . . ? Cl10 C50 H50A 107.7 . . ? Cl12 C50 H50A 107.7 . . ? Cl11 C50 H50A 107.7 . . ? Cl4 C48 Cl5 110.8(8) . . ? Cl4 C48 Cl6 104.8(8) . . ? Cl5 C48 Cl6 105.1(8) . . ? Cl4 C48 H48A 111.9 . . ? Cl5 C48 H48A 111.9 . . ? Cl6 C48 H48A 111.9 . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.588 _refine_diff_density_min -0.472 _refine_diff_density_rms 0.065 # Attachment 'B716331B-ic12839.cif' data_ic12839 _database_code_depnum_ccdc_archive 'CCDC 664528' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C43 H43 F6 N2 O4 P' _chemical_formula_weight 796.76 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' F F 0.0171 0.0103 '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 Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 12.50690(10) _cell_length_b 17.0522(2) _cell_length_c 18.6392(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3975.19(7) _cell_formula_units_Z 4 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 51136 _cell_measurement_theta_min 1 _cell_measurement_theta_max 27.5 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.331 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1664 _exptl_absorpt_coefficient_mu 0.142 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.809 _exptl_absorpt_correction_T_max 0.957 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(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 'Nonius KappaCCD' _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 26553 _diffrn_reflns_av_R_equivalents 0.0400 _diffrn_reflns_av_sigmaI/netI 0.0332 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 1.96 _diffrn_reflns_theta_max 27.48 _reflns_number_total 9055 _reflns_number_gt 6808 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Nonius BV)' _computing_cell_refinement 'HKL Denzo & Scalepack (Otwinowski & Minor)' _computing_data_reduction 'HKL Denzo & Scalepack (Otwinowski & Minor)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXTL _computing_publication_material 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. Because of the large correlation between thermal parameters, the restraint was necessary for convergence of the refinement process. In large supermolecular structure with poor data to parameter ratios, they often are needed with geometrical and anisotropic displacement parameters restraints. ; _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^)+(0.0950P)^2^+0.4777P] 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 0.022(3) _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_abs_structure_Flack 0.03(13) _refine_ls_number_reflns 9055 _refine_ls_number_parameters 524 _refine_ls_number_restraints 30 _refine_ls_R_factor_all 0.0761 _refine_ls_R_factor_gt 0.0546 _refine_ls_wR_factor_ref 0.1700 _refine_ls_wR_factor_gt 0.1510 _refine_ls_goodness_of_fit_ref 1.063 _refine_ls_restrained_S_all 1.062 _refine_ls_shift/su_max 0.024 _refine_ls_shift/su_mean 0.001 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.41921(14) 0.96509(9) 0.25818(8) 0.0561(4) Uani 1 1 d . . . O2 O 0.49042(15) 1.16648(10) 0.42924(10) 0.0645(4) Uani 1 1 d . . . O3 O 0.91696(19) 1.01977(14) 0.53387(18) 0.1056(9) Uani 1 1 d . . . O4 O 0.65163(19) 0.67918(10) 0.39081(11) 0.0791(6) Uani 1 1 d . . . N1 N 0.36920(16) 1.11282(12) 0.31717(10) 0.0547(4) Uani 1 1 d . A . C1 C 0.3542(2) 1.01943(17) 0.22031(14) 0.0681(7) Uani 1 1 d . . . H1A H 0.2989 0.9915 0.1943 0.082 Uiso 1 1 calc R . . H1B H 0.3975 1.0479 0.1858 0.082 Uiso 1 1 calc R . . C2 C 0.3040(2) 1.07595(14) 0.27167(12) 0.0559(5) Uani 1 1 d . . . C3 C 0.1944(2) 1.09025(16) 0.26832(15) 0.0671(6) Uani 1 1 d . . . H3A H 0.1513 1.0621 0.2369 0.080 Uiso 1 1 calc R . . C4 C 0.1511(2) 1.14656(19) 0.31215(17) 0.0749(8) Uani 1 1 d . . . H4A H 0.0786 1.1584 0.3101 0.090 Uiso 1 1 calc R . . C5 C 0.2173(2) 1.18486(18) 0.35909(15) 0.0712(7) Uani 1 1 d . A . H5A H 0.1900 1.2231 0.3896 0.085 Uiso 1 1 calc R . . C6 C 0.3258(2) 1.16629(14) 0.36086(13) 0.0582(6) Uani 1 1 d . . . C7 C 0.3977(3) 1.20952(17) 0.41138(18) 0.0770(8) Uani 1 1 d U A . H7A H 0.4187 1.2588 0.3896 0.092 Uiso 1 1 calc R . . H7B H 0.3585 1.2214 0.4549 0.092 Uiso 1 1 calc R . . C8 C 0.5507(8) 1.2066(6) 0.4841(7) 0.080(2) Uani 0.66(3) 1 d PU A 1 H8A H 0.5105 1.2082 0.5285 0.096 Uiso 0.66(3) 1 calc PR A 1 H8B H 0.5661 1.2600 0.4693 0.096 Uiso 0.66(3) 1 calc PR A 1 C8' C 0.5732(17) 1.2159(10) 0.4576(15) 0.082(3) Uani 0.34(3) 1 d PU A 2 H8'1 H 0.5438 1.2528 0.4919 0.099 Uiso 0.34(3) 1 calc PR A 2 H8'2 H 0.6075 1.2451 0.4193 0.099 Uiso 0.34(3) 1 calc PR A 2 C9 C 0.6536(3) 1.16102(18) 0.49420(18) 0.0765(8) Uani 1 1 d U . . C10 C 0.7447(3) 1.16322(17) 0.45236(16) 0.0763(8) Uani 1 1 d . A . H10A H 0.7482 1.1976 0.4137 0.092 Uiso 1 1 calc R . . C11 C 0.8302(2) 1.11517(18) 0.46709(16) 0.0730(7) Uani 1 1 d . . . H11A H 0.8909 1.1172 0.4383 0.088 Uiso 1 1 calc R A . C12 C 0.8265(2) 1.06420(18) 0.52417(18) 0.0731(7) Uani 1 1 d . A . C13 C 0.7381(3) 1.0625(2) 0.56858(17) 0.0823(8) Uani 1 1 d . . . H13A H 0.7361 1.0293 0.6082 0.099 Uiso 1 1 calc R A . C14 C 0.6520(3) 1.1113(2) 0.55286(19) 0.0840(9) Uani 1 1 d . A . H14A H 0.5922 1.1105 0.5824 0.101 Uiso 1 1 calc R . . C15 C 0.9104(3) 0.9471(2) 0.5723(2) 0.1086(14) Uani 1 1 d . . . H15A H 0.8644 0.9538 0.6137 0.130 Uiso 1 1 calc R . . H15B H 0.9810 0.9329 0.5895 0.130 Uiso 1 1 calc R . . C16 C 0.8674(3) 0.88152(18) 0.52625(18) 0.0787(8) Uani 1 1 d . . . C17 C 0.9263(3) 0.8530(2) 0.4695(2) 0.0950(10) Uani 1 1 d . . . H17A H 0.9903 0.8771 0.4570 0.114 Uiso 1 1 calc R . . C18 C 0.8909(3) 0.7888(2) 0.43080(18) 0.0901(9) Uani 1 1 d . . . H18A H 0.9313 0.7707 0.3923 0.108 Uiso 1 1 calc R . . C19 C 0.7975(2) 0.75146(16) 0.44806(14) 0.0682(7) Uani 1 1 d . . . C20 C 0.7374(3) 0.7801(2) 0.50360(17) 0.0803(8) Uani 1 1 d . . . H20A H 0.6732 0.7559 0.5156 0.096 Uiso 1 1 calc R . . C21 C 0.7716(3) 0.8448(2) 0.54188(17) 0.0845(9) Uani 1 1 d . . . H21A H 0.7292 0.8641 0.5789 0.101 Uiso 1 1 calc R . . C22 C 0.7636(3) 0.67989(18) 0.40715(18) 0.0877(10) Uani 1 1 d . . . H22A H 0.8038 0.6772 0.3627 0.105 Uiso 1 1 calc R . . H22B H 0.7809 0.6336 0.4351 0.105 Uiso 1 1 calc R . . C23 C 0.6135(2) 0.73601(13) 0.34499(13) 0.0615(6) Uani 1 1 d . . . C24 C 0.6751(2) 0.77902(15) 0.29867(14) 0.0614(6) Uani 1 1 d . . . H24A H 0.7488 0.7720 0.2972 0.074 Uiso 1 1 calc R . . C25 C 0.6256(2) 0.83374(14) 0.25364(12) 0.0581(5) Uani 1 1 d . . . H25A H 0.6670 0.8629 0.2219 0.070 Uiso 1 1 calc R . . C26 C 0.51628(19) 0.84522(13) 0.25557(12) 0.0538(5) Uani 1 1 d . . . C27 C 0.4557(2) 0.80035(17) 0.30256(15) 0.0673(6) Uani 1 1 d . . . H27A H 0.3819 0.8066 0.3040 0.081 Uiso 1 1 calc R . . C28 C 0.5044(3) 0.74647(16) 0.34722(16) 0.0718(7) Uani 1 1 d . . . H28A H 0.4633 0.7171 0.3790 0.086 Uiso 1 1 calc R . . C29 C 0.4615(2) 0.90594(16) 0.21077(13) 0.0654(7) Uani 1 1 d . . . H29A H 0.5118 0.9293 0.1775 0.078 Uiso 1 1 calc R . . H29B H 0.4040 0.8822 0.1834 0.078 Uiso 1 1 calc R . . N2 N 0.52208(16) 0.99939(12) 0.39334(11) 0.0534(4) Uani 1 1 d . . . C30 C 0.6362(2) 0.97553(15) 0.38694(13) 0.0593(6) Uani 1 1 d . . . H30A H 0.6389 0.9194 0.3786 0.071 Uiso 1 1 calc R . . H30B H 0.6714 0.9858 0.4323 0.071 Uiso 1 1 calc R . . C31 C 0.69798(19) 1.01565(14) 0.32863(13) 0.0552(5) Uani 1 1 d . . . C32 C 0.6630(2) 1.08212(15) 0.29297(15) 0.0626(6) Uani 1 1 d . . . H32A H 0.5945 1.1013 0.3010 0.075 Uiso 1 1 calc R . . C33 C 0.7302(2) 1.11967(19) 0.24562(18) 0.0791(8) Uani 1 1 d . . . H33A H 0.7071 1.1652 0.2230 0.095 Uiso 1 1 calc R . . C34 C 0.8304(3) 1.0913(2) 0.2311(2) 0.0838(9) Uani 1 1 d . . . H34A H 0.8749 1.1170 0.1988 0.101 Uiso 1 1 calc R . . C35 C 0.8644(2) 1.0241(2) 0.2652(2) 0.0852(9) Uani 1 1 d . . . H35A H 0.9320 1.0041 0.2555 0.102 Uiso 1 1 calc R . . C36 C 0.7994(2) 0.98654(17) 0.31323(17) 0.0709(7) Uani 1 1 d . . . H36A H 0.8232 0.9411 0.3358 0.085 Uiso 1 1 calc R . . C37 C 0.4660(3) 0.95256(17) 0.45020(16) 0.0732(7) Uani 1 1 d . . . H37A H 0.4570 0.8991 0.4336 0.088 Uiso 1 1 calc R . . H37B H 0.5100 0.9512 0.4930 0.088 Uiso 1 1 calc R . . C38 C 0.3589(2) 0.98623(16) 0.46848(13) 0.0638(6) Uani 1 1 d . . . C39 C 0.3503(2) 1.0370(2) 0.52610(15) 0.0753(8) Uani 1 1 d . . . H39A H 0.4105 1.0491 0.5531 0.090 Uiso 1 1 calc R . . C40 C 0.2533(3) 1.0694(2) 0.54357(19) 0.0909(10) Uani 1 1 d . . . H40A H 0.2487 1.1031 0.5827 0.109 Uiso 1 1 calc R . . C41 C 0.1649(3) 1.0536(3) 0.5052(2) 0.0983(12) Uani 1 1 d . . . H41A H 0.1002 1.0771 0.5171 0.118 Uiso 1 1 calc R . . C42 C 0.1708(3) 1.0020(3) 0.4477(2) 0.0957(11) Uani 1 1 d . . . H42A H 0.1095 0.9903 0.4215 0.115 Uiso 1 1 calc R . . C43 C 0.2676(3) 0.96761(19) 0.42916(16) 0.0778(8) Uani 1 1 d . . . H43A H 0.2715 0.9326 0.3910 0.093 Uiso 1 1 calc R . . P1 P 0.58142(8) 0.66592(5) 0.76189(5) 0.0827(3) Uani 1 1 d . . . F1 F 0.5695(4) 0.6081(2) 0.69772(16) 0.1789(16) Uani 1 1 d . . . F2 F 0.5764(4) 0.7231(3) 0.8266(2) 0.2051(18) Uani 1 1 d . . . F3 F 0.7002(2) 0.6658(3) 0.7687(3) 0.236(2) Uani 1 1 d . . . F4 F 0.5726(3) 0.59379(18) 0.81416(15) 0.1435(11) Uani 1 1 d . . . F5 F 0.4561(2) 0.6664(2) 0.7593(2) 0.1819(15) Uani 1 1 d . . . F6 F 0.5841(5) 0.7350(2) 0.7102(2) 0.236(3) Uani 1 1 d . . . H2 H 0.4929(19) 0.9939(14) 0.3532(14) 0.045(6) Uiso 1 1 d . . . H1 H 0.518(2) 1.0531(18) 0.4026(14) 0.058(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 O1 0.0687(9) 0.0510(8) 0.0485(7) -0.0029(7) -0.0091(7) 0.0117(7) O2 0.0706(10) 0.0507(9) 0.0722(10) -0.0104(8) -0.0109(9) 0.0057(8) O3 0.0703(13) 0.0809(14) 0.166(3) 0.0055(16) -0.0346(15) -0.0070(12) O4 0.1139(16) 0.0465(9) 0.0770(12) 0.0062(9) -0.0335(11) 0.0038(10) N1 0.0586(10) 0.0508(10) 0.0547(10) 0.0027(8) 0.0001(8) 0.0106(9) C1 0.0854(18) 0.0683(15) 0.0507(12) -0.0013(11) -0.0115(12) 0.0268(14) C2 0.0624(13) 0.0553(12) 0.0501(11) 0.0060(10) -0.0017(10) 0.0114(10) C3 0.0625(14) 0.0701(15) 0.0685(15) 0.0080(13) -0.0052(12) 0.0059(12) C4 0.0569(14) 0.0840(19) 0.0838(19) 0.0118(16) 0.0067(13) 0.0150(14) C5 0.0709(16) 0.0707(16) 0.0720(16) -0.0003(13) 0.0122(13) 0.0209(13) C6 0.0649(13) 0.0515(12) 0.0583(13) 0.0038(10) 0.0029(11) 0.0107(11) C7 0.093(2) 0.0561(14) 0.0820(17) -0.0129(13) -0.0113(15) 0.0223(14) C8 0.091(4) 0.063(3) 0.086(4) -0.025(3) -0.016(3) 0.009(3) C8' 0.092(5) 0.063(4) 0.091(6) -0.019(5) -0.019(5) 0.001(4) C9 0.0818(18) 0.0614(15) 0.0862(19) -0.0229(14) -0.0220(15) -0.0003(14) C10 0.098(2) 0.0616(15) 0.0690(16) -0.0084(13) -0.0190(16) -0.0131(15) C11 0.0775(17) 0.0698(16) 0.0717(16) -0.0126(14) -0.0011(14) -0.0158(14) C12 0.0619(15) 0.0662(15) 0.0912(19) -0.0065(14) -0.0207(14) -0.0124(13) C13 0.091(2) 0.0847(19) 0.0711(17) 0.0026(16) -0.0159(16) -0.0205(17) C14 0.0737(17) 0.095(2) 0.083(2) -0.0251(18) 0.0029(15) -0.0173(17) C15 0.115(3) 0.080(2) 0.131(3) 0.007(2) -0.075(3) -0.011(2) C16 0.0869(19) 0.0695(16) 0.0797(18) 0.0048(15) -0.0392(16) -0.0017(15) C17 0.094(2) 0.100(3) 0.091(2) 0.023(2) -0.012(2) -0.016(2) C18 0.100(2) 0.101(2) 0.0694(17) 0.0096(18) 0.0022(17) 0.008(2) C19 0.0802(17) 0.0674(15) 0.0570(13) 0.0044(12) -0.0162(13) 0.0132(13) C20 0.0722(17) 0.087(2) 0.0813(18) -0.0098(16) -0.0083(15) -0.0100(16) C21 0.085(2) 0.096(2) 0.0728(17) -0.0258(17) -0.0130(15) 0.0011(17) C22 0.120(3) 0.0651(17) 0.0785(18) -0.0008(14) -0.0286(18) 0.0252(17) C23 0.0896(18) 0.0401(10) 0.0549(13) -0.0014(10) -0.0159(12) 0.0002(11) C24 0.0674(14) 0.0586(13) 0.0581(13) -0.0081(11) -0.0046(11) 0.0114(11) C25 0.0755(15) 0.0496(11) 0.0493(11) -0.0001(10) 0.0042(11) 0.0045(11) C26 0.0665(14) 0.0467(11) 0.0480(11) -0.0042(9) -0.0058(10) 0.0044(10) C27 0.0648(14) 0.0592(14) 0.0778(16) 0.0037(13) -0.0045(12) -0.0048(12) C28 0.0847(19) 0.0546(14) 0.0761(17) 0.0109(13) -0.0040(14) -0.0137(13) C29 0.0871(17) 0.0598(14) 0.0492(12) -0.0062(11) -0.0060(12) 0.0172(13) N2 0.0610(11) 0.0523(11) 0.0469(10) -0.0007(8) -0.0047(9) -0.0004(9) C30 0.0659(14) 0.0567(12) 0.0552(12) -0.0036(11) -0.0080(11) 0.0104(11) C31 0.0551(12) 0.0523(12) 0.0583(12) -0.0086(10) -0.0086(10) 0.0031(10) C32 0.0604(13) 0.0600(14) 0.0674(14) 0.0008(12) -0.0011(11) 0.0133(12) C33 0.0813(18) 0.0683(16) 0.0878(19) 0.0120(16) 0.0058(16) 0.0076(14) C34 0.0685(17) 0.083(2) 0.100(2) 0.0039(18) 0.0161(16) -0.0046(15) C35 0.0549(15) 0.0826(19) 0.118(3) -0.0035(19) 0.0078(16) 0.0046(14) C36 0.0587(14) 0.0595(14) 0.0946(19) 0.0014(14) -0.0049(13) 0.0107(12) C37 0.0899(19) 0.0656(15) 0.0640(15) 0.0124(13) 0.0076(14) 0.0007(14) C38 0.0713(15) 0.0676(14) 0.0525(13) 0.0121(11) 0.0025(11) -0.0121(13) C39 0.0777(18) 0.093(2) 0.0555(14) 0.0038(14) 0.0058(13) -0.0185(16) C40 0.082(2) 0.116(3) 0.0747(18) -0.0020(19) 0.0236(17) -0.012(2) C41 0.074(2) 0.131(3) 0.090(2) 0.016(2) 0.0247(18) -0.010(2) C42 0.0719(19) 0.124(3) 0.091(2) 0.030(2) -0.0063(17) -0.0326(19) C43 0.087(2) 0.0838(19) 0.0628(15) 0.0113(14) -0.0061(14) -0.0260(16) P1 0.0859(5) 0.0751(5) 0.0872(5) 0.0036(4) -0.0076(4) -0.0001(4) F1 0.300(5) 0.132(2) 0.1047(17) -0.0237(18) 0.037(2) -0.042(3) F2 0.241(4) 0.190(4) 0.184(3) -0.100(3) -0.054(3) 0.014(3) F3 0.0774(17) 0.293(6) 0.337(6) 0.095(5) 0.024(3) -0.006(2) F4 0.171(3) 0.140(2) 0.1200(19) 0.0487(18) -0.0283(19) -0.0192(19) F5 0.108(2) 0.179(3) 0.258(4) -0.020(4) -0.044(2) 0.0147(19) F6 0.379(6) 0.134(3) 0.195(3) 0.080(3) -0.115(4) -0.120(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.420(3) . ? O1 C29 1.441(3) . ? O2 C7 1.412(3) . ? O2 C8' 1.435(17) . ? O2 C8 1.443(8) . ? O3 C12 1.374(4) . ? O3 C15 1.434(4) . ? O4 C23 1.377(3) . ? O4 C22 1.433(4) . ? N1 C2 1.334(3) . ? N1 C6 1.338(3) . ? C1 C2 1.497(3) . ? C1 H1A 0.9700 . ? C1 H1B 0.9700 . ? C2 C3 1.393(4) . ? C3 C4 1.372(4) . ? C3 H3A 0.9300 . ? C4 C5 1.370(4) . ? C4 H4A 0.9300 . ? C5 C6 1.393(4) . ? C5 H5A 0.9300 . ? C6 C7 1.496(4) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C9 1.516(8) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C8' C9 1.535(18) . ? C8' H8'1 0.9700 . ? C8' H8'2 0.9700 . ? C9 C10 1.381(5) . ? C9 C14 1.384(5) . ? C10 C11 1.375(5) . ? C10 H10A 0.9300 . ? C11 C12 1.375(5) . ? C11 H11A 0.9300 . ? C12 C13 1.382(5) . ? C13 C14 1.392(5) . ? C13 H13A 0.9300 . ? C14 H14A 0.9300 . ? C15 C16 1.509(4) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 C17 1.378(5) . ? C16 C21 1.383(5) . ? C17 C18 1.384(5) . ? C17 H17A 0.9300 . ? C18 C19 1.368(5) . ? C18 H18A 0.9300 . ? C19 C20 1.370(4) . ? C19 C22 1.500(4) . ? C20 C21 1.382(4) . ? C20 H20A 0.9300 . ? C21 H21A 0.9300 . ? C22 H22A 0.9700 . ? C22 H22B 0.9700 . ? C23 C24 1.371(4) . ? C23 C28 1.376(4) . ? C24 C25 1.399(3) . ? C24 H24A 0.9300 . ? C25 C26 1.382(4) . ? C25 H25A 0.9300 . ? C26 C27 1.388(4) . ? C26 C29 1.497(3) . ? C27 C28 1.381(4) . ? C27 H27A 0.9300 . ? C28 H28A 0.9300 . ? C29 H29A 0.9700 . ? C29 H29B 0.9700 . ? N2 C30 1.489(3) . ? N2 C37 1.501(3) . ? N2 H2 0.84(3) . ? N2 H1 0.93(3) . ? C30 C31 1.499(4) . ? C30 H30A 0.9700 . ? C30 H30B 0.9700 . ? C31 C32 1.385(3) . ? C31 C36 1.392(3) . ? C32 C33 1.376(4) . ? C32 H32A 0.9300 . ? C33 C34 1.371(4) . ? C33 H33A 0.9300 . ? C34 C35 1.377(5) . ? C34 H34A 0.9300 . ? C35 C36 1.368(5) . ? C35 H35A 0.9300 . ? C36 H36A 0.9300 . ? C37 C38 1.497(4) . ? C37 H37A 0.9700 . ? C37 H37B 0.9700 . ? C38 C39 1.383(4) . ? C38 C43 1.393(4) . ? C39 C40 1.372(5) . ? C39 H39A 0.9300 . ? C40 C41 1.344(5) . ? C40 H40A 0.9300 . ? C41 C42 1.390(6) . ? C41 H41A 0.9300 . ? C42 C43 1.389(5) . ? C42 H42A 0.9300 . ? C43 H43A 0.9300 . ? P1 F3 1.491(3) . ? P1 F6 1.522(3) . ? P1 F2 1.552(3) . ? P1 F1 1.558(3) . ? P1 F5 1.568(3) . ? P1 F4 1.573(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 O1 C29 111.20(17) . . ? C7 O2 C8' 112.0(7) . . ? C7 O2 C8 110.4(3) . . ? C8' O2 C8 23.7(8) . . ? C12 O3 C15 119.7(3) . . ? C23 O4 C22 117.7(2) . . ? C2 N1 C6 117.4(2) . . ? O1 C1 C2 110.03(19) . . ? O1 C1 H1A 109.7 . . ? C2 C1 H1A 109.7 . . ? O1 C1 H1B 109.7 . . ? C2 C1 H1B 109.7 . . ? H1A C1 H1B 108.2 . . ? N1 C2 C3 123.2(2) . . ? N1 C2 C1 116.9(2) . . ? C3 C2 C1 119.8(2) . . ? C4 C3 C2 118.9(3) . . ? C4 C3 H3A 120.5 . . ? C2 C3 H3A 120.5 . . ? C5 C4 C3 118.4(3) . . ? C5 C4 H4A 120.8 . . ? C3 C4 H4A 120.8 . . ? C4 C5 C6 119.7(3) . . ? C4 C5 H5A 120.2 . . ? C6 C5 H5A 120.2 . . ? N1 C6 C5 122.4(2) . . ? N1 C6 C7 118.3(2) . . ? C5 C6 C7 119.2(2) . . ? O2 C7 C6 112.7(2) . . ? O2 C7 H7A 109.1 . . ? C6 C7 H7A 109.1 . . ? O2 C7 H7B 109.1 . . ? C6 C7 H7B 109.1 . . ? H7A C7 H7B 107.8 . . ? O2 C8 C9 106.8(5) . . ? O2 C8 H8A 110.4 . . ? C9 C8 H8A 110.4 . . ? O2 C8 H8B 110.4 . . ? C9 C8 H8B 110.4 . . ? H8A C8 H8B 108.6 . . ? O2 C8' C9 106.2(11) . . ? O2 C8' H8'1 110.5 . . ? C9 C8' H8'1 110.5 . . ? O2 C8' H8'2 110.5 . . ? C9 C8' H8'2 110.5 . . ? H8'1 C8' H8'2 108.7 . . ? C10 C9 C14 118.4(3) . . ? C10 C9 C8 128.0(7) . . ? C14 C9 C8 113.6(7) . . ? C10 C9 C8' 105.8(12) . . ? C14 C9 C8' 135.7(12) . . ? C8 C9 C8' 22.3(8) . . ? C11 C10 C9 120.8(3) . . ? C11 C10 H10A 119.6 . . ? C9 C10 H10A 119.6 . . ? C12 C11 C10 120.3(3) . . ? C12 C11 H11A 119.8 . . ? C10 C11 H11A 119.8 . . ? O3 C12 C11 115.0(3) . . ? O3 C12 C13 124.6(3) . . ? C11 C12 C13 120.3(3) . . ? C12 C13 C14 118.7(3) . . ? C12 C13 H13A 120.7 . . ? C14 C13 H13A 120.7 . . ? C9 C14 C13 121.5(3) . . ? C9 C14 H14A 119.3 . . ? C13 C14 H14A 119.3 . . ? O3 C15 C16 112.1(3) . . ? O3 C15 H15A 109.2 . . ? C16 C15 H15A 109.2 . . ? O3 C15 H15B 109.2 . . ? C16 C15 H15B 109.2 . . ? H15A C15 H15B 107.9 . . ? C17 C16 C21 117.8(3) . . ? C17 C16 C15 120.5(4) . . ? C21 C16 C15 121.6(4) . . ? C16 C17 C18 120.5(3) . . ? C16 C17 H17A 119.7 . . ? C18 C17 H17A 119.7 . . ? C19 C18 C17 121.3(3) . . ? C19 C18 H18A 119.4 . . ? C17 C18 H18A 119.4 . . ? C18 C19 C20 118.7(3) . . ? C18 C19 C22 120.0(3) . . ? C20 C19 C22 121.2(3) . . ? C19 C20 C21 120.3(3) . . ? C19 C20 H20A 119.8 . . ? C21 C20 H20A 119.8 . . ? C20 C21 C16 121.4(3) . . ? C20 C21 H21A 119.3 . . ? C16 C21 H21A 119.3 . . ? O4 C22 C19 113.0(3) . . ? O4 C22 H22A 109.0 . . ? C19 C22 H22A 109.0 . . ? O4 C22 H22B 109.0 . . ? C19 C22 H22B 109.0 . . ? H22A C22 H22B 107.8 . . ? C24 C23 C28 120.5(2) . . ? C24 C23 O4 124.9(3) . . ? C28 C23 O4 114.6(2) . . ? C23 C24 C25 119.1(2) . . ? C23 C24 H24A 120.5 . . ? C25 C24 H24A 120.5 . . ? C26 C25 C24 121.1(2) . . ? C26 C25 H25A 119.4 . . ? C24 C25 H25A 119.4 . . ? C25 C26 C27 118.6(2) . . ? C25 C26 C29 122.5(2) . . ? C27 C26 C29 118.9(2) . . ? C28 C27 C26 120.4(3) . . ? C28 C27 H27A 119.8 . . ? C26 C27 H27A 119.8 . . ? C23 C28 C27 120.3(3) . . ? C23 C28 H28A 119.8 . . ? C27 C28 H28A 119.8 . . ? O1 C29 C26 108.06(18) . . ? O1 C29 H29A 110.1 . . ? C26 C29 H29A 110.1 . . ? O1 C29 H29B 110.1 . . ? C26 C29 H29B 110.1 . . ? H29A C29 H29B 108.4 . . ? C30 N2 C37 111.0(2) . . ? C30 N2 H2 108.4(16) . . ? C37 N2 H2 111.5(17) . . ? C30 N2 H1 109.3(16) . . ? C37 N2 H1 111.6(16) . . ? H2 N2 H1 105(2) . . ? N2 C30 C31 115.3(2) . . ? N2 C30 H30A 108.4 . . ? C31 C30 H30A 108.4 . . ? N2 C30 H30B 108.4 . . ? C31 C30 H30B 108.4 . . ? H30A C30 H30B 107.5 . . ? C32 C31 C36 118.7(2) . . ? C32 C31 C30 124.0(2) . . ? C36 C31 C30 117.2(2) . . ? C33 C32 C31 119.7(3) . . ? C33 C32 H32A 120.1 . . ? C31 C32 H32A 120.1 . . ? C34 C33 C32 121.3(3) . . ? C34 C33 H33A 119.3 . . ? C32 C33 H33A 119.3 . . ? C33 C34 C35 119.0(3) . . ? C33 C34 H34A 120.5 . . ? C35 C34 H34A 120.5 . . ? C36 C35 C34 120.6(3) . . ? C36 C35 H35A 119.7 . . ? C34 C35 H35A 119.7 . . ? C35 C36 C31 120.6(3) . . ? C35 C36 H36A 119.7 . . ? C31 C36 H36A 119.7 . . ? C38 C37 N2 112.0(2) . . ? C38 C37 H37A 109.2 . . ? N2 C37 H37A 109.2 . . ? C38 C37 H37B 109.2 . . ? N2 C37 H37B 109.2 . . ? H37A C37 H37B 107.9 . . ? C39 C38 C43 119.1(3) . . ? C39 C38 C37 119.1(3) . . ? C43 C38 C37 121.8(3) . . ? C40 C39 C38 120.4(3) . . ? C40 C39 H39A 119.8 . . ? C38 C39 H39A 119.8 . . ? C41 C40 C39 121.4(4) . . ? C41 C40 H40A 119.3 . . ? C39 C40 H40A 119.3 . . ? C40 C41 C42 119.6(4) . . ? C40 C41 H41A 120.2 . . ? C42 C41 H41A 120.2 . . ? C43 C42 C41 120.4(3) . . ? C43 C42 H42A 119.8 . . ? C41 C42 H42A 119.8 . . ? C42 C43 C38 119.2(3) . . ? C42 C43 H43A 120.4 . . ? C38 C43 H43A 120.4 . . ? F3 P1 F6 91.9(3) . . ? F3 P1 F2 88.5(3) . . ? F6 P1 F2 90.4(3) . . ? F3 P1 F1 99.2(3) . . ? F6 P1 F1 90.4(2) . . ? F2 P1 F1 172.2(3) . . ? F3 P1 F5 176.8(3) . . ? F6 P1 F5 89.9(3) . . ? F2 P1 F5 88.9(3) . . ? F1 P1 F5 83.4(2) . . ? F3 P1 F4 90.9(2) . . ? F6 P1 F4 177.1(3) . . ? F2 P1 F4 90.4(2) . . ? F1 P1 F4 88.50(18) . . ? F5 P1 F4 87.3(2) . . ? 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 N2 H2 O1 0.84(3) 2.06(3) 2.889(3) 173(2) . N2 H1 O2 0.93(3) 2.03(3) 2.953(3) 172(2) . N2 H2 N1 0.84(3) 2.64(2) 3.068(3) 113(2) . N2 H2 N1 0.84(3) 2.64(2) 3.068(3) 113(2) . _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.311 _refine_diff_density_min -0.199 _refine_diff_density_rms 0.034