# Supplementary Material (ESI) for Dalton Transactions # This journal is (c) The Royal Society of Chemistry 2008 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Prof Paul Derek Beer' _publ_contact_author_email PAUL.BEER@CHEM.OX.AC.UK _publ_section_title ; Metalloporphyrin Anion Sensors: The Effect of the Metal Centre on the Anion Binding Properties of Amide Functionalized and Tetraphenyl Metalloporphyrins ; loop_ _publ_author_name 'P. D. Beer' 'David Cormode' 'Michael Drew' 'Raymond Jagessar' # Attachment 'beer.cif' data_1 _database_code_depnum_ccdc_archive 'CCDC 686999' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C81 H72 N8 O14' _chemical_formula_weight 1381.47 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 P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 12.727(7) _cell_length_b 25.271(7) _cell_length_c 23.357(9) _cell_angle_alpha 90.00 _cell_angle_beta 94.490(10) _cell_angle_gamma 90.00 _cell_volume 7489(5) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description parallelopiped _exptl_crystal_colour white _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.225 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2904 _exptl_absorpt_coefficient_mu 0.085 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_standards_number ? _diffrn_measurement_device 'Marresearch Image Plate' _diffrn_measurement_method '95 frames at 2^o intervals, counting time 10 min.' _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 17241 _diffrn_reflns_av_R_equivalents 0.0654 _diffrn_reflns_av_sigmaI/netI 0.1000 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -26 _diffrn_reflns_limit_k_max 26 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 2.79 _diffrn_reflns_theta_max 22.46 _reflns_number_total 9051 _reflns_number_gt 4906 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'XDS (Kabsch, 1988)' _computing_cell_refinement XDS _computing_data_reduction XDS _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics PLATON(Spek,2004) _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 fullcycle _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; w=1/[\s^2^(Fo^2^)+(0.1954P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3 ; _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 9051 _refine_ls_number_parameters 952 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1757 _refine_ls_R_factor_gt 0.0944 _refine_ls_wR_factor_ref 0.3061 _refine_ls_wR_factor_gt 0.2456 _refine_ls_goodness_of_fit_ref 0.954 _refine_ls_restrained_S_all 0.954 _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 0.9390(3) 0.2250(2) 0.6748(2) 0.0416(13) Uani 1 1 d . . . H1 H 0.8729 0.2323 0.6704 0.050 Uiso 0.50 1 calc PR . . N11 N 0.8164(3) 0.3228(2) 0.6715(2) 0.0403(13) Uani 1 1 d . . . H11 H 0.8010 0.2898 0.6678 0.048 Uiso 0.50 1 calc PR . . N17 N 0.6225(3) 0.2640(2) 0.6548(2) 0.0402(12) Uani 1 1 d . . . H17 H 0.6884 0.2563 0.6555 0.048 Uiso 0.50 1 calc PR . . N23 N 0.7460(4) 0.16611(19) 0.6626(2) 0.0411(13) Uani 1 1 d . . . H23 H 0.7623 0.1989 0.6592 0.049 Uiso 0.50 1 calc PR . . N37 N 1.1340(4) 0.3711(2) 0.6124(3) 0.0643(17) Uani 1 1 d . . . H37 H 1.0701 0.3612 0.6036 0.077 Uiso 1 1 calc R . . C2 C 0.9808(4) 0.1760(3) 0.6748(3) 0.0445(16) Uani 1 1 d . . . C3 C 1.0923(5) 0.1820(3) 0.6792(3) 0.0566(19) Uani 1 1 d . . . H3 H 1.1411 0.1548 0.6776 0.068 Uiso 1 1 calc R . . C4 C 1.1151(5) 0.2329(3) 0.6861(3) 0.059(2) Uani 1 1 d . . . H4 H 1.1823 0.2474 0.6917 0.070 Uiso 1 1 calc R . . C5 C 1.0191(4) 0.2611(3) 0.6832(3) 0.0459(17) Uani 1 1 d . . . C6 C 1.0087(4) 0.3156(2) 0.6885(2) 0.0376(15) Uani 1 1 d . . . C7 C 0.9150(4) 0.3437(3) 0.6810(3) 0.0409(15) Uani 1 1 d . . . C8 C 0.9081(5) 0.3996(3) 0.6816(3) 0.0539(18) Uani 1 1 d . . . H8 H 0.9640 0.4232 0.6869 0.065 Uiso 1 1 calc R . . C9 C 0.8054(5) 0.4121(3) 0.6732(3) 0.060(2) Uani 1 1 d . . . H9 H 0.7770 0.4460 0.6707 0.072 Uiso 1 1 calc R . . C10 C 0.7480(5) 0.3632(3) 0.6688(3) 0.0487(17) Uani 1 1 d . . . C12 C 0.6374(5) 0.3596(3) 0.6621(3) 0.0454(16) Uani 1 1 d . . . C13 C 0.5804(4) 0.3146(3) 0.6568(3) 0.0423(16) Uani 1 1 d . . . C14 C 0.4675(4) 0.3077(3) 0.6519(3) 0.0561(19) Uani 1 1 d . . . H14 H 0.4181 0.3349 0.6505 0.067 Uiso 1 1 calc R . . C15 C 0.4455(5) 0.2566(3) 0.6495(3) 0.0500(17) Uani 1 1 d . . . H15 H 0.3785 0.2417 0.6470 0.060 Uiso 1 1 calc R . . C16 C 0.5421(4) 0.2287(3) 0.6515(3) 0.0409(15) Uani 1 1 d . . . C18 C 0.5516(4) 0.1740(3) 0.6543(3) 0.0420(16) Uani 1 1 d . . . C19 C 0.6456(5) 0.1455(3) 0.6613(3) 0.0499(17) Uani 1 1 d . . . C20 C 0.6551(5) 0.0888(3) 0.6691(3) 0.0559(19) Uani 1 1 d . . . H20 H 0.5995 0.0649 0.6696 0.067 Uiso 1 1 calc R . . C21 C 0.7576(5) 0.0768(3) 0.6756(3) 0.0558(18) Uani 1 1 d . . . H21 H 0.7865 0.0433 0.6822 0.067 Uiso 1 1 calc R . . C22 C 0.8143(5) 0.1251(2) 0.6704(3) 0.0432(16) Uani 1 1 d . . . C23 C 0.9246(5) 0.1296(2) 0.6734(3) 0.0412(16) Uani 1 1 d . . . C31 C 1.1053(4) 0.3473(3) 0.7078(3) 0.0451(16) Uani 1 1 d . . . C32 C 1.1639(5) 0.3747(3) 0.6702(3) 0.0521(18) Uani 1 1 d . . . C33 C 1.2486(5) 0.4058(3) 0.6919(4) 0.074(2) Uani 1 1 d . . . H33 H 1.2867 0.4262 0.6676 0.089 Uiso 1 1 calc R . . C34 C 1.2735(6) 0.4055(4) 0.7498(5) 0.103(3) Uani 1 1 d . . . H34 H 1.3324 0.4245 0.7641 0.123 Uiso 1 1 calc R . . C35 C 1.2179(7) 0.3794(4) 0.7869(4) 0.099(3) Uani 1 1 d . . . H35 H 1.2356 0.3818 0.8262 0.119 Uiso 1 1 calc R . . C36 C 1.1337(6) 0.3489(3) 0.7659(4) 0.077(2) Uani 1 1 d . . . H36 H 1.0960 0.3293 0.7910 0.092 Uiso 1 1 calc R . . C38 C 1.1914(6) 0.3812(3) 0.5687(3) 0.069(2) Uani 1 1 d . . . O39 O 1.2823(5) 0.3992(3) 0.5758(3) 0.109(2) Uani 1 1 d . . . C40 C 1.1462(6) 0.3680(4) 0.5097(3) 0.074(2) Uani 1 1 d . . . C41 C 1.1903(6) 0.3931(3) 0.4642(4) 0.075(2) Uani 1 1 d . . . H41 H 1.2433 0.4181 0.4717 0.090 Uiso 1 1 calc R . . C42 C 1.1566(7) 0.3813(4) 0.4086(4) 0.081(2) Uani 1 1 d . . . C43 C 1.0778(7) 0.3439(4) 0.3983(4) 0.078(2) Uani 1 1 d . . . C44 C 1.0350(7) 0.3205(4) 0.4425(4) 0.100(3) Uani 1 1 d . . . H44 H 0.9806 0.2964 0.4348 0.120 Uiso 1 1 calc R . . C45 C 1.0689(7) 0.3310(4) 0.4995(4) 0.104(3) Uani 1 1 d . . . H45 H 1.0399 0.3134 0.5295 0.124 Uiso 1 1 calc R . . O46 O 1.1947(4) 0.4044(3) 0.3617(3) 0.102(2) Uani 1 1 d . . . C47 C 1.2809(7) 0.4409(4) 0.3729(4) 0.104(3) Uani 1 1 d . . . H47A H 1.3037 0.4536 0.3372 0.124 Uiso 1 1 calc R . . H47B H 1.3383 0.4232 0.3941 0.124 Uiso 1 1 calc R . . H47C H 1.2580 0.4702 0.3949 0.124 Uiso 1 1 calc R . . O48 O 1.0491(5) 0.3334(3) 0.3420(3) 0.109(2) Uani 1 1 d . . . C49 C 0.9807(9) 0.2909(5) 0.3296(5) 0.127(4) Uani 1 1 d . . . H49A H 0.9625 0.2895 0.2890 0.152 Uiso 1 1 calc R . . H49B H 0.9179 0.2956 0.3493 0.152 Uiso 1 1 calc R . . H49C H 1.0147 0.2585 0.3420 0.152 Uiso 1 1 calc R . . C51 C 0.5799(4) 0.4111(3) 0.6685(3) 0.0467(17) Uani 1 1 d . . . C52 C 0.5902(5) 0.4356(3) 0.7201(3) 0.064(2) Uani 1 1 d . . . H52 H 0.6288 0.4200 0.7510 0.077 Uiso 1 1 calc R . . C53 C 0.5418(6) 0.4853(3) 0.7265(4) 0.075(2) Uani 1 1 d . . . H53 H 0.5504 0.5028 0.7616 0.090 Uiso 1 1 calc R . . C54 C 0.4825(6) 0.5078(4) 0.6818(5) 0.083(3) Uani 1 1 d . . . H54 H 0.4509 0.5406 0.6861 0.100 Uiso 1 1 calc R . . C55 C 0.4703(5) 0.4821(3) 0.6316(4) 0.070(2) Uani 1 1 d . . . H55 H 0.4285 0.4972 0.6015 0.084 Uiso 1 1 calc R . . C56 C 0.5181(5) 0.4335(3) 0.6231(3) 0.0524(18) Uani 1 1 d . . . N57 N 0.5013(4) 0.4086(2) 0.5695(3) 0.0597(16) Uani 1 1 d . . . H57 H 0.4375 0.3996 0.5590 0.072 Uiso 1 1 calc R . . C58 C 0.5744(7) 0.3972(3) 0.5329(3) 0.071(2) Uani 1 1 d . . . O59 O 0.6672(4) 0.4110(3) 0.5442(3) 0.0963(19) Uani 1 1 d . . . C60 C 0.5387(6) 0.3713(3) 0.4787(3) 0.069(2) Uani 1 1 d . . . C61 C 0.5964(6) 0.3776(3) 0.4311(4) 0.072(2) Uani 1 1 d . . . H61 H 0.6599 0.3960 0.4350 0.087 Uiso 1 1 calc R . . C62 C 0.5619(7) 0.3572(4) 0.3779(4) 0.084(3) Uani 1 1 d . . . C63 C 0.4707(8) 0.3278(4) 0.3739(4) 0.083(3) Uani 1 1 d . . . C64 C 0.4147(6) 0.3187(4) 0.4219(4) 0.088(3) Uani 1 1 d . . . H64 H 0.3545 0.2977 0.4189 0.105 Uiso 1 1 calc R . . C65 C 0.4491(6) 0.3411(4) 0.4740(4) 0.078(2) Uani 1 1 d . . . H65 H 0.4113 0.3356 0.5060 0.094 Uiso 1 1 calc R . . O66 O 0.6114(5) 0.3633(3) 0.3294(3) 0.0964(19) Uani 1 1 d . . . C67 C 0.7166(8) 0.3821(5) 0.3354(4) 0.115(4) Uani 1 1 d . . . H67A H 0.7170 0.4188 0.3459 0.138 Uiso 1 1 calc R . . H67B H 0.7481 0.3779 0.2997 0.138 Uiso 1 1 calc R . . H67C H 0.7561 0.3622 0.3648 0.138 Uiso 1 1 calc R . . O68 O 0.4387(5) 0.3105(3) 0.3195(3) 0.108(2) Uani 1 1 d . . . C69 C 0.3362(8) 0.2846(5) 0.3106(5) 0.131(4) Uani 1 1 d . . . H69A H 0.3369 0.2524 0.3324 0.157 Uiso 1 1 calc R . . H69B H 0.3219 0.2766 0.2705 0.157 Uiso 1 1 calc R . . H69C H 0.2825 0.3077 0.3229 0.157 Uiso 1 1 calc R . . C71 C 0.4545(4) 0.1400(3) 0.6469(3) 0.0458(17) Uani 1 1 d . . . C72 C 0.4094(5) 0.1218(3) 0.6940(4) 0.063(2) Uani 1 1 d . . . H72 H 0.4368 0.1314 0.7306 0.075 Uiso 1 1 calc R . . C73 C 0.3215(5) 0.0884(3) 0.6871(4) 0.066(2) Uani 1 1 d . . . H73 H 0.2929 0.0739 0.7190 0.079 Uiso 1 1 calc R . . C74 C 0.2788(6) 0.0778(3) 0.6337(4) 0.075(2) Uani 1 1 d . . . H74 H 0.2186 0.0568 0.6294 0.090 Uiso 1 1 calc R . . C75 C 0.3208(5) 0.0964(3) 0.5863(4) 0.075(2) Uani 1 1 d . . . H75 H 0.2904 0.0879 0.5500 0.090 Uiso 1 1 calc R . . C76 C 0.4105(5) 0.1288(3) 0.5924(3) 0.0573(19) Uani 1 1 d . . . N77 N 0.4598(5) 0.1502(3) 0.5450(3) 0.080(2) Uani 1 1 d . . . H77 H 0.5145 0.1690 0.5552 0.096 Uiso 1 1 calc R . . C78 C 0.4401(7) 0.1476(4) 0.4899(4) 0.094(3) Uani 1 1 d . . . O79 O 0.3681(7) 0.1196(5) 0.4704(4) 0.194(5) Uani 1 1 d . . . C80 C 0.5093(6) 0.1763(4) 0.4543(4) 0.077(2) Uani 1 1 d . . . C81 C 0.4868(7) 0.1743(4) 0.3960(4) 0.088(3) Uani 1 1 d . . . H81 H 0.4276 0.1563 0.3805 0.105 Uiso 1 1 calc R . . C82 C 0.5523(7) 0.1991(4) 0.3610(4) 0.080(2) Uani 1 1 d . . . H82 H 0.5355 0.1983 0.3216 0.096 Uiso 1 1 calc R . . C83 C 0.6410(7) 0.2250(4) 0.3815(4) 0.077(2) Uani 1 1 d . . . C84 C 0.6643(6) 0.2277(4) 0.4398(3) 0.069(2) Uani 1 1 d . . . C85 C 0.6017(6) 0.2030(3) 0.4761(4) 0.074(2) Uani 1 1 d . . . H85 H 0.6196 0.2036 0.5155 0.089 Uiso 1 1 calc R . . O86 O 0.7538(4) 0.2532(3) 0.4570(2) 0.0937(19) Uani 1 1 d . . . C87 C 0.7773(8) 0.2599(6) 0.5180(4) 0.145(5) Uani 1 1 d . . . H87A H 0.8243 0.2894 0.5248 0.174 Uiso 1 1 calc R . . H87B H 0.8101 0.2284 0.5339 0.174 Uiso 1 1 calc R . . H87C H 0.7132 0.2665 0.5359 0.174 Uiso 1 1 calc R . . O88 O 0.7107(5) 0.2503(2) 0.3502(2) 0.0864(17) Uani 1 1 d . . . C89 C 0.6903(7) 0.2480(4) 0.2881(4) 0.102(3) Uani 1 1 d . . . H89A H 0.7382 0.2712 0.2705 0.122 Uiso 1 1 calc R . . H89B H 0.6191 0.2590 0.2777 0.122 Uiso 1 1 calc R . . H89C H 0.7001 0.2124 0.2752 0.122 Uiso 1 1 calc R . . C90 C 0.9845(4) 0.0785(3) 0.6800(3) 0.0490(17) Uani 1 1 d . . . C91 C 1.0449(5) 0.0702(3) 0.7312(3) 0.0548(18) Uani 1 1 d . . . H91 H 1.0504 0.0967 0.7589 0.066 Uiso 1 1 calc R . . C92 C 1.0961(5) 0.0235(3) 0.7412(3) 0.064(2) Uani 1 1 d . . . H92 H 1.1326 0.0175 0.7767 0.077 Uiso 1 1 calc R . . C93 C 1.0949(5) -0.0148(3) 0.6999(4) 0.063(2) Uani 1 1 d . . . H93 H 1.1321 -0.0462 0.7064 0.076 Uiso 1 1 calc R . . C94 C 1.0377(5) -0.0059(3) 0.6490(3) 0.064(2) Uani 1 1 d . . . H94 H 1.0367 -0.0315 0.6203 0.077 Uiso 1 1 calc R . . C95 C 0.9815(5) 0.0401(3) 0.6390(3) 0.0484(17) Uani 1 1 d . . . N96 N 0.9162(4) 0.0422(3) 0.5878(3) 0.0628(17) Uani 1 1 d . . . H96 H 0.8751 0.0156 0.5806 0.075 Uiso 1 1 calc R . . C97 C 0.9110(6) 0.0806(4) 0.5497(4) 0.070(2) Uani 1 1 d . . . O98 O 0.9757(5) 0.1179(2) 0.5526(2) 0.0879(17) Uani 1 1 d . . . C99 C 0.8294(6) 0.0773(3) 0.5024(3) 0.066(2) Uani 1 1 d . . . C100 C 0.8411(6) 0.1005(3) 0.4507(3) 0.067(2) Uani 1 1 d . . . H100 H 0.9023 0.1195 0.4457 0.080 Uiso 1 1 calc R . . C101 C 0.7649(6) 0.0967(3) 0.4054(4) 0.072(2) Uani 1 1 d . . . C102 C 0.6743(6) 0.0677(3) 0.4136(4) 0.070(2) Uani 1 1 d . . . C103 C 0.6584(7) 0.0461(4) 0.4650(4) 0.089(3) Uani 1 1 d . . . H103 H 0.5958 0.0286 0.4707 0.107 Uiso 1 1 calc R . . C104 C 0.7379(7) 0.0505(3) 0.5098(4) 0.083(3) Uani 1 1 d . . . H104 H 0.7284 0.0350 0.5451 0.100 Uiso 1 1 calc R . . O105 O 0.7738(5) 0.1182(3) 0.3525(3) 0.0925(18) Uani 1 1 d . . . C106 C 0.8662(7) 0.1495(4) 0.3448(4) 0.098(3) Uani 1 1 d . . . H10A H 0.8588 0.1665 0.3079 0.118 Uiso 1 1 calc R . . H10B H 0.9272 0.1270 0.3470 0.118 Uiso 1 1 calc R . . H10C H 0.8742 0.1759 0.3744 0.118 Uiso 1 1 calc R . . O107 O 0.6045(5) 0.0642(3) 0.3664(3) 0.0966(19) Uani 1 1 d . . . C108 C 0.5083(8) 0.0385(4) 0.3746(5) 0.116(4) Uani 1 1 d . . . H10D H 0.4648 0.0382 0.3391 0.140 Uiso 1 1 calc R . . H10E H 0.4726 0.0569 0.4033 0.140 Uiso 1 1 calc R . . H10F H 0.5222 0.0027 0.3869 0.140 Uiso 1 1 calc R . . O200 O 0.8015(10) -0.0624(5) 0.5789(6) 0.105(4) Uiso 0.50 1 d P . . O201 O 0.8536(14) -0.0722(7) 0.5521(8) 0.150(6) Uiso 0.50 1 d P . . O202 O 0.8905(19) 0.4088(10) 0.5385(11) 0.234(10) Uiso 0.50 1 d P . . O300 O 1.1365 0.1790 0.4196 0.249 Uiso 0.50 1 d P . . H300 H 1.1787 0.2026 0.4289 0.299 Uiso 0.50 1 d P . . C301 C 1.0997 0.1578 0.4674 0.128 Uiso 0.50 1 d P . . H30A H 1.1513 0.1332 0.4847 0.154 Uiso 0.50 1 d P . . H30B H 1.0355 0.1382 0.4568 0.154 Uiso 0.50 1 d P . . C302 C 1.0784 0.1977 0.5083 0.258 Uiso 0.50 1 d P . . H30C H 1.1437 0.2120 0.5249 0.309 Uiso 0.50 1 d P . . H30D H 1.0400 0.1825 0.5380 0.309 Uiso 0.50 1 d P . . H30E H 1.0373 0.2254 0.4895 0.309 Uiso 0.50 1 d P . . 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 0.029(3) 0.047(4) 0.048(3) 0.000(3) 0.004(2) 0.001(3) N11 0.034(3) 0.038(3) 0.048(3) -0.003(3) -0.002(2) 0.002(2) N17 0.037(3) 0.046(4) 0.037(3) -0.003(2) -0.001(2) -0.004(3) N23 0.044(3) 0.035(3) 0.044(3) -0.001(2) 0.001(2) -0.004(3) N37 0.050(3) 0.091(5) 0.054(4) 0.000(3) 0.011(3) -0.025(3) C2 0.042(4) 0.039(4) 0.052(4) 0.002(3) 0.000(3) 0.007(3) C3 0.036(4) 0.054(5) 0.080(6) -0.005(4) 0.005(3) 0.018(3) C4 0.035(4) 0.061(6) 0.079(6) -0.010(4) 0.003(3) -0.001(3) C5 0.035(4) 0.057(5) 0.046(4) 0.003(3) 0.005(3) 0.000(3) C6 0.033(4) 0.043(4) 0.037(4) 0.000(3) 0.004(3) -0.006(3) C7 0.041(4) 0.042(4) 0.038(4) -0.003(3) -0.003(3) 0.000(3) C8 0.044(4) 0.059(5) 0.059(5) -0.011(4) 0.001(3) -0.011(3) C9 0.053(5) 0.049(5) 0.078(6) -0.004(4) -0.004(3) 0.002(4) C10 0.043(4) 0.052(5) 0.050(4) -0.004(3) -0.006(3) -0.005(3) C12 0.042(4) 0.045(4) 0.048(4) 0.000(3) -0.007(3) -0.002(3) C13 0.040(4) 0.041(4) 0.045(4) 0.003(3) -0.002(3) 0.002(3) C14 0.030(4) 0.067(6) 0.071(5) 0.006(4) 0.003(3) 0.003(3) C15 0.035(4) 0.047(5) 0.067(5) 0.006(4) 0.000(3) -0.008(3) C16 0.034(4) 0.041(4) 0.046(4) 0.001(3) -0.003(3) 0.000(3) C18 0.031(4) 0.055(5) 0.040(4) -0.002(3) 0.003(3) 0.004(3) C19 0.047(4) 0.048(5) 0.055(5) -0.002(3) 0.004(3) -0.015(3) C20 0.038(4) 0.052(5) 0.078(5) -0.004(4) 0.005(3) -0.003(3) C21 0.056(5) 0.046(5) 0.065(5) 0.002(4) 0.007(3) 0.001(3) C22 0.045(4) 0.037(4) 0.048(4) -0.004(3) 0.003(3) 0.005(3) C23 0.045(4) 0.038(4) 0.040(4) -0.008(3) -0.002(3) 0.001(3) C31 0.038(4) 0.051(4) 0.047(5) 0.000(3) 0.009(3) -0.002(3) C32 0.044(4) 0.067(5) 0.045(5) -0.013(4) 0.003(3) 0.002(3) C33 0.055(5) 0.090(7) 0.077(7) -0.021(5) 0.007(4) -0.023(4) C34 0.058(5) 0.158(10) 0.091(8) -0.028(7) 0.002(5) -0.025(5) C35 0.087(6) 0.160(10) 0.048(6) -0.015(6) -0.007(5) -0.032(6) C36 0.063(5) 0.103(7) 0.062(6) -0.005(5) -0.006(4) -0.015(4) C38 0.052(5) 0.092(7) 0.062(6) 0.010(4) 0.000(4) -0.005(4) O39 0.070(4) 0.170(7) 0.089(5) 0.008(4) 0.010(3) -0.035(4) C40 0.061(5) 0.100(7) 0.060(6) 0.009(5) -0.001(4) -0.006(4) C41 0.061(5) 0.097(7) 0.068(6) 0.010(5) 0.008(4) -0.012(4) C42 0.076(6) 0.103(8) 0.064(7) 0.007(5) 0.011(5) -0.005(5) C43 0.088(6) 0.102(7) 0.044(6) 0.006(5) 0.010(4) -0.007(5) C44 0.104(7) 0.125(9) 0.073(7) -0.007(6) 0.014(5) -0.044(6) C45 0.100(7) 0.139(9) 0.072(7) -0.013(6) 0.010(5) -0.056(6) O46 0.085(4) 0.136(6) 0.085(5) 0.032(4) 0.007(3) -0.011(4) C47 0.088(7) 0.120(9) 0.104(8) 0.039(6) 0.014(5) -0.017(6) O48 0.127(5) 0.127(6) 0.072(5) 0.006(4) 0.009(4) -0.010(4) C49 0.151(10) 0.134(10) 0.094(8) -0.012(7) 0.001(7) -0.042(8) C51 0.035(4) 0.042(4) 0.061(5) 0.000(4) -0.006(3) -0.002(3) C52 0.051(4) 0.069(6) 0.071(6) -0.012(4) -0.003(4) 0.001(4) C53 0.061(5) 0.076(6) 0.088(7) -0.020(5) 0.010(4) -0.007(4) C54 0.066(5) 0.063(6) 0.121(9) -0.017(6) 0.009(5) 0.006(4) C55 0.058(5) 0.054(5) 0.098(7) 0.002(5) 0.007(4) 0.007(4) C56 0.037(4) 0.054(5) 0.065(5) 0.000(4) 0.002(3) -0.006(3) N57 0.044(3) 0.065(4) 0.070(5) -0.002(3) -0.001(3) -0.001(3) C58 0.061(5) 0.088(6) 0.063(6) 0.000(5) -0.002(4) 0.005(4) O59 0.060(4) 0.137(6) 0.093(5) -0.012(4) 0.010(3) -0.007(3) C60 0.061(5) 0.089(6) 0.057(5) 0.007(5) 0.000(4) -0.002(4) C61 0.061(5) 0.078(6) 0.077(7) 0.008(5) -0.001(4) 0.011(4) C62 0.081(6) 0.098(8) 0.071(7) 0.000(6) -0.005(5) 0.017(5) C63 0.091(7) 0.084(7) 0.072(7) -0.008(5) -0.009(5) 0.014(5) C64 0.067(5) 0.101(8) 0.095(8) 0.004(6) 0.004(5) 0.003(5) C65 0.079(6) 0.091(7) 0.063(6) -0.002(5) -0.003(4) 0.000(5) O66 0.107(5) 0.105(5) 0.079(5) 0.003(4) 0.023(4) 0.019(4) C67 0.104(8) 0.142(10) 0.104(9) 0.019(7) 0.030(6) 0.023(7) O68 0.117(5) 0.121(6) 0.084(5) -0.003(4) -0.013(4) 0.018(4) C69 0.108(8) 0.164(12) 0.116(9) -0.011(8) -0.025(6) -0.003(8) C71 0.039(4) 0.046(4) 0.053(5) -0.003(3) 0.002(3) 0.002(3) C72 0.049(4) 0.064(5) 0.076(6) 0.004(4) 0.009(4) 0.009(4) C73 0.046(4) 0.062(5) 0.091(7) 0.022(5) 0.017(4) -0.004(4) C74 0.046(5) 0.072(6) 0.108(8) -0.002(5) 0.012(5) -0.010(4) C75 0.042(4) 0.085(6) 0.095(7) -0.018(5) -0.006(4) -0.011(4) C76 0.050(4) 0.056(5) 0.067(5) -0.005(4) 0.006(4) 0.004(3) N77 0.069(4) 0.097(6) 0.071(5) -0.008(4) -0.009(4) -0.025(4) C78 0.065(6) 0.148(10) 0.068(7) -0.031(6) -0.008(5) -0.015(5) O79 0.142(7) 0.332(15) 0.105(6) -0.037(7) -0.004(5) -0.124(8) C80 0.065(5) 0.105(7) 0.061(6) -0.012(5) 0.009(4) -0.013(5) C81 0.078(6) 0.108(8) 0.074(7) -0.014(6) -0.008(5) -0.003(5) C82 0.092(6) 0.087(7) 0.058(6) -0.003(5) -0.011(5) 0.004(5) C83 0.081(6) 0.080(6) 0.071(7) 0.012(5) 0.009(5) 0.018(5) C84 0.061(5) 0.099(7) 0.047(5) -0.003(5) -0.001(4) -0.002(4) C85 0.061(5) 0.101(7) 0.061(5) -0.005(5) -0.001(4) -0.005(4) O86 0.081(4) 0.136(6) 0.064(4) 0.001(4) 0.008(3) -0.015(4) C87 0.129(9) 0.230(15) 0.077(8) 0.002(8) 0.004(6) -0.077(9) O88 0.108(4) 0.094(5) 0.058(4) 0.004(3) 0.003(3) 0.011(3) C89 0.113(7) 0.131(9) 0.061(6) -0.001(6) 0.011(5) 0.025(6) C90 0.036(4) 0.048(5) 0.061(5) -0.006(4) -0.007(3) 0.005(3) C91 0.053(4) 0.045(5) 0.065(5) 0.002(4) -0.001(4) 0.005(3) C92 0.057(4) 0.069(6) 0.067(5) 0.015(5) -0.003(4) 0.001(4) C93 0.062(4) 0.045(5) 0.082(6) -0.004(5) -0.003(4) 0.005(3) C94 0.059(4) 0.061(5) 0.071(6) -0.004(4) -0.005(4) -0.002(4) C95 0.044(4) 0.040(4) 0.061(5) -0.003(4) 0.000(3) 0.009(3) N96 0.062(4) 0.066(5) 0.058(4) 0.001(4) -0.006(3) 0.005(3) C97 0.058(5) 0.080(7) 0.069(6) -0.015(5) -0.005(4) 0.001(4) O98 0.093(4) 0.093(5) 0.075(4) 0.004(3) -0.008(3) -0.015(4) C99 0.069(5) 0.069(6) 0.059(6) 0.001(4) -0.002(4) -0.004(4) C100 0.070(5) 0.066(6) 0.063(6) 0.001(4) 0.001(4) 0.004(4) C101 0.078(6) 0.066(6) 0.069(6) -0.007(5) -0.008(5) 0.016(4) C102 0.073(5) 0.085(6) 0.050(5) -0.006(5) -0.014(4) 0.007(5) C103 0.087(6) 0.108(8) 0.070(7) 0.001(6) -0.008(5) 0.002(5) C104 0.094(6) 0.091(7) 0.062(6) 0.010(5) -0.014(5) 0.000(5) O105 0.105(5) 0.106(5) 0.066(4) 0.002(4) 0.002(3) 0.025(4) C106 0.102(7) 0.093(7) 0.101(8) 0.015(6) 0.023(5) 0.002(6) O107 0.096(4) 0.104(5) 0.086(5) -0.010(4) -0.022(4) 0.005(4) C108 0.105(8) 0.121(9) 0.117(9) -0.015(7) -0.026(6) 0.002(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 N1 C2 1.348(7) . ? N1 C5 1.371(8) . ? N11 C10 1.341(8) . ? N11 C7 1.364(7) . ? N17 C16 1.354(7) . ? N17 C13 1.389(7) . ? N23 C22 1.357(7) . ? N23 C19 1.377(7) . ? N37 C38 1.327(9) . ? N37 C32 1.377(8) . ? C2 C23 1.372(8) . ? C2 C3 1.422(8) . ? C3 C4 1.324(9) . ? C4 C5 1.412(8) . ? C5 C6 1.390(8) . ? C6 C7 1.388(8) . ? C6 C31 1.506(8) . ? C7 C8 1.415(9) . ? C8 C9 1.344(9) . ? C9 C10 1.434(9) . ? C10 C12 1.407(8) . ? C12 C13 1.351(8) . ? C12 C51 1.505(9) . ? C13 C14 1.444(8) . ? C14 C15 1.321(9) . ? C15 C16 1.415(8) . ? C16 C18 1.390(8) . ? C18 C19 1.395(8) . ? C18 C71 1.504(8) . ? C19 C20 1.448(9) . ? C20 C21 1.337(8) . ? C21 C22 1.428(9) . ? C22 C23 1.405(8) . ? C23 C90 1.502(8) . ? C31 C36 1.378(10) . ? C31 C32 1.381(9) . ? C32 C33 1.397(9) . ? C33 C34 1.364(11) . ? C34 C35 1.336(12) . ? C35 C36 1.378(11) . ? C38 O39 1.241(8) . ? C38 C40 1.489(10) . ? C40 C45 1.364(11) . ? C40 C41 1.393(10) . ? C41 C42 1.368(11) . ? C42 O46 1.363(10) . ? C42 C43 1.386(11) . ? C43 C44 1.340(11) . ? C43 O48 1.364(9) . ? C44 C45 1.391(12) . ? O46 C47 1.442(10) . ? O48 C49 1.398(11) . ? C51 C52 1.351(9) . ? C51 C56 1.391(9) . ? C52 C53 1.411(11) . ? C53 C54 1.363(11) . ? C54 C55 1.338(11) . ? C55 C56 1.392(10) . ? C56 N57 1.403(8) . ? N57 C58 1.344(9) . ? C58 O59 1.241(8) . ? C58 C60 1.464(11) . ? C60 C65 1.369(10) . ? C60 C61 1.390(11) . ? C61 C62 1.384(11) . ? C62 O66 1.346(10) . ? C62 C63 1.375(12) . ? C63 O68 1.374(10) . ? C63 C64 1.394(12) . ? C64 C65 1.382(11) . ? O66 C67 1.418(10) . ? O68 C69 1.460(11) . ? C71 C72 1.359(9) . ? C71 C76 1.379(9) . ? C72 C73 1.400(10) . ? C73 C74 1.347(11) . ? C74 C75 1.352(11) . ? C75 C76 1.403(10) . ? C76 N77 1.421(9) . ? N77 C78 1.295(10) . ? C78 O79 1.218(10) . ? C78 C80 1.451(12) . ? C80 C81 1.370(11) . ? C80 C85 1.415(10) . ? C81 C82 1.364(12) . ? C82 C83 1.359(11) . ? C83 O88 1.353(10) . ? C83 C84 1.374(11) . ? C84 O86 1.342(9) . ? C84 C85 1.360(10) . ? O86 C87 1.443(11) . ? O88 C89 1.454(10) . ? C90 C95 1.362(9) . ? C90 C91 1.386(9) . ? C91 C92 1.360(9) . ? C92 C93 1.365(10) . ? C93 C94 1.364(10) . ? C94 C95 1.374(9) . ? C95 N96 1.403(8) . ? N96 C97 1.315(10) . ? C97 O98 1.249(9) . ? C97 C99 1.458(10) . ? C99 C100 1.361(10) . ? C99 C104 1.368(10) . ? C100 C101 1.380(10) . ? C101 O105 1.363(10) . ? C101 C102 1.392(11) . ? C102 C103 1.350(11) . ? C102 O107 1.363(9) . ? C103 C104 1.401(10) . ? O105 C106 1.441(10) . ? O107 C108 1.412(10) . ? O200 O201 0.979(18) . ? O300 C301 1.3536 . ? C301 C302 1.4299 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 N1 C5 108.8(5) . . ? C10 N11 C7 107.3(5) . . ? C16 N17 C13 108.4(5) . . ? C22 N23 C19 107.3(5) . . ? C38 N37 C32 128.0(6) . . ? N1 C2 C23 125.4(6) . . ? N1 C2 C3 107.0(6) . . ? C23 C2 C3 127.5(6) . . ? C4 C3 C2 108.7(6) . . ? C3 C4 C5 107.6(6) . . ? N1 C5 C6 126.7(5) . . ? N1 C5 C4 107.6(6) . . ? C6 C5 C4 125.7(6) . . ? C7 C6 C5 125.6(5) . . ? C7 C6 C31 116.0(5) . . ? C5 C6 C31 118.2(5) . . ? N11 C7 C6 126.4(6) . . ? N11 C7 C8 109.3(5) . . ? C6 C7 C8 124.3(5) . . ? C9 C8 C7 107.1(6) . . ? C8 C9 C10 107.0(6) . . ? N11 C10 C12 126.6(6) . . ? N11 C10 C9 109.1(5) . . ? C12 C10 C9 124.3(6) . . ? C13 C12 C10 126.2(6) . . ? C13 C12 C51 118.4(5) . . ? C10 C12 C51 115.0(6) . . ? C12 C13 N17 125.0(5) . . ? C12 C13 C14 129.3(6) . . ? N17 C13 C14 105.7(6) . . ? C15 C14 C13 109.1(6) . . ? C14 C15 C16 107.8(5) . . ? N17 C16 C18 126.1(5) . . ? N17 C16 C15 109.0(5) . . ? C18 C16 C15 124.8(5) . . ? C16 C18 C19 126.2(5) . . ? C16 C18 C71 119.6(5) . . ? C19 C18 C71 114.1(6) . . ? N23 C19 C18 126.4(6) . . ? N23 C19 C20 107.7(5) . . ? C18 C19 C20 126.0(5) . . ? C21 C20 C19 108.1(6) . . ? C20 C21 C22 106.9(6) . . ? N23 C22 C23 124.8(6) . . ? N23 C22 C21 110.0(5) . . ? C23 C22 C21 125.1(6) . . ? C2 C23 C22 126.1(6) . . ? C2 C23 C90 118.2(5) . . ? C22 C23 C90 115.5(5) . . ? C36 C31 C32 119.8(6) . . ? C36 C31 C6 117.1(6) . . ? C32 C31 C6 123.1(6) . . ? N37 C32 C31 117.9(6) . . ? N37 C32 C33 122.6(7) . . ? C31 C32 C33 119.5(7) . . ? C34 C33 C32 117.9(8) . . ? C35 C34 C33 123.5(8) . . ? C34 C35 C36 118.8(8) . . ? C35 C36 C31 120.3(8) . . ? O39 C38 N37 122.0(7) . . ? O39 C38 C40 119.7(7) . . ? N37 C38 C40 118.2(7) . . ? C45 C40 C41 120.5(8) . . ? C45 C40 C38 122.5(8) . . ? C41 C40 C38 117.0(7) . . ? C42 C41 C40 120.7(8) . . ? O46 C42 C41 124.5(8) . . ? O46 C42 C43 116.8(8) . . ? C41 C42 C43 118.8(8) . . ? C44 C43 O48 124.2(9) . . ? C44 C43 C42 120.0(8) . . ? O48 C43 C42 115.8(8) . . ? C43 C44 C45 122.6(9) . . ? C40 C45 C44 117.5(9) . . ? C42 O46 C47 116.1(7) . . ? C43 O48 C49 117.7(8) . . ? C52 C51 C56 120.1(6) . . ? C52 C51 C12 118.2(6) . . ? C56 C51 C12 121.7(6) . . ? C51 C52 C53 119.4(7) . . ? C54 C53 C52 120.6(8) . . ? C55 C54 C53 119.2(8) . . ? C54 C55 C56 122.1(8) . . ? C51 C56 C55 118.6(7) . . ? C51 C56 N57 122.4(6) . . ? C55 C56 N57 119.0(7) . . ? C58 N57 C56 126.8(6) . . ? O59 C58 N57 120.0(7) . . ? O59 C58 C60 122.3(8) . . ? N57 C58 C60 117.5(7) . . ? C65 C60 C61 119.2(8) . . ? C65 C60 C58 121.3(8) . . ? C61 C60 C58 119.5(8) . . ? C62 C61 C60 121.7(8) . . ? O66 C62 C63 116.9(9) . . ? O66 C62 C61 125.1(9) . . ? C63 C62 C61 117.9(9) . . ? O68 C63 C62 115.0(9) . . ? O68 C63 C64 123.9(9) . . ? C62 C63 C64 121.1(9) . . ? C65 C64 C63 119.6(9) . . ? C60 C65 C64 120.3(9) . . ? C62 O66 C67 117.1(8) . . ? C63 O68 C69 118.2(8) . . ? C72 C71 C76 120.6(6) . . ? C72 C71 C18 119.8(6) . . ? C76 C71 C18 119.6(6) . . ? C71 C72 C73 119.7(8) . . ? C74 C73 C72 119.2(7) . . ? C73 C74 C75 122.1(7) . . ? C74 C75 C76 119.4(8) . . ? C71 C76 C75 118.8(7) . . ? C71 C76 N77 117.9(6) . . ? C75 C76 N77 123.2(7) . . ? C78 N77 C76 133.9(7) . . ? O79 C78 N77 118.9(10) . . ? O79 C78 C80 123.3(9) . . ? N77 C78 C80 117.8(8) . . ? C81 C80 C85 118.6(8) . . ? C81 C80 C78 117.5(8) . . ? C85 C80 C78 123.8(8) . . ? C82 C81 C80 119.2(8) . . ? C83 C82 C81 122.7(8) . . ? O88 C83 C82 126.8(8) . . ? O88 C83 C84 114.4(8) . . ? C82 C83 C84 118.7(8) . . ? O86 C84 C85 124.1(7) . . ? O86 C84 C83 115.6(8) . . ? C85 C84 C83 120.3(8) . . ? C84 C85 C80 120.4(8) . . ? C84 O86 C87 117.2(6) . . ? C83 O88 C89 116.5(7) . . ? C95 C90 C91 118.8(6) . . ? C95 C90 C23 123.7(6) . . ? C91 C90 C23 117.5(6) . . ? C92 C91 C90 120.4(7) . . ? C91 C92 C93 120.9(7) . . ? C94 C93 C92 118.4(7) . . ? C93 C94 C95 121.5(7) . . ? C90 C95 C94 119.9(6) . . ? C90 C95 N96 123.6(6) . . ? C94 C95 N96 116.3(6) . . ? C97 N96 C95 126.9(6) . . ? O98 C97 N96 121.4(7) . . ? O98 C97 C99 120.8(9) . . ? N96 C97 C99 117.7(8) . . ? C100 C99 C104 118.5(7) . . ? C100 C99 C97 121.7(8) . . ? C104 C99 C97 119.7(8) . . ? C99 C100 C101 122.0(8) . . ? O105 C101 C100 124.3(8) . . ? O105 C101 C102 117.5(7) . . ? C100 C101 C102 118.2(8) . . ? C103 C102 O107 124.1(8) . . ? C103 C102 C101 121.2(8) . . ? O107 C102 C101 114.7(8) . . ? C102 C103 C104 118.8(9) . . ? C99 C104 C103 121.2(8) . . ? C101 O105 C106 117.3(7) . . ? C102 O107 C108 116.0(8) . . ? O300 C301 C302 111.5 . . ? _diffrn_measured_fraction_theta_max 0.929 _diffrn_reflns_theta_full 22.46 _diffrn_measured_fraction_theta_full 0.929 _refine_diff_density_max 0.460 _refine_diff_density_min -0.187 _refine_diff_density_rms 0.056 _publ_section_references ; Kabsch, W. (1988), J.Appl.Cryst 21 916-932. Sheldrick, G.M. (1997) SHELX97 program for crystallography refinement. University of Gottingen, Germany. Spek, A.L., (2004) PLATON-94 program, Utrecht University, The Netherlands ; #===END