# Supplementary Material (ESI) for ChemComm # This journal is © The Royal Society of Chemistry 2000 # CCDC Number: 182/1564 ############################################################################ # # # This Supplementary Material is written in the Crystallographic # # Information File (CIF) format. For further details see: S.R. Hall, # # F.H. Allen and I.D. Brown, Acta Cryst. (1991) A47, 655-685. # # # ############################################################################ data_2.H2O ############################################################################ # # _publ_requested_journal 'Chemical Communications' _publ_section_title ; Intramolecular conformational control in a cyclic peptide composed of alternating (L)-proline and substituted 3-aminobenzoic acid subunits ; loop_ _publ_author_name _publ_author_address 'Stefan Kubik' ; Institut f\"ur Organische und Makromolekulare Chemie Heinrich-Heine-Universit\"at Universit\"atsstrasse 1 D-40225 D\"usseldorf Germany ; 'Richard Goddard' ; Max-Planck-Institut f\"ur Kohlenforschung Kaiser-Wilhelm-Platz 1 D-45470 M\"ulheim an der Ruhr Germany ; # # ############################################################################ _chemical_name_systematic ; cyclo-tris[(L)-prolyl-alpha-3-amino-4(methoxycarbonyl)benzoyl] water solvate ; _chemical_name_common 'cyclo[(L)Pro-AMB]~3~ water solvate' _chemical_compound_source 'see paper' _chemical_formula_moiety 'C42 H42 N6 O12, H2 O' _chemical_formula_sum 'C42 H44 N6 O13' _chemical_formula_weight 840.83 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' _symmetry_Int_Tables_number 19 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 13.2214(6) _cell_length_b 17.0958(8) _cell_length_c 18.0413(8) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 4077.9(3) _cell_formula_units_Z 4 _cell_measurement_temperature 100 _cell_measurement_reflns_used 8192 _cell_measurement_theta_min 1.64 _cell_measurement_theta_max 33.16 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.58 _exptl_crystal_size_mid 0.54 _exptl_crystal_size_min 0.44 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.370 _exptl_crystal_density_method none _exptl_crystal_F_000 1768 _exptl_absorpt_coefficient_mu 0.103 _exptl_absorpt_correction_type gaussian _exptl_absorpt_process_details 'XPREP, Siemens (1995)' _exptl_absorpt_correction_T_min 0.94754 _exptl_absorpt_correction_T_max 0.96358 _publ_section_exptl_prep ; The crystal was mounted on a glass capillary and cooled by an N~2~ gas stream. ; _diffrn_ambient_temperature 100 _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 'Siemens SMART' _diffrn_measurement_method 'CCD \w-scan' _diffrn_standards_number 0 _diffrn_standards_decay_% 0.0 _diffrn_reflns_number 44640 _diffrn_reflns_av_R_equivalents 0.0423 _diffrn_reflns_av_sigmaI/netI 0.0867 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -26 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 1.64 _diffrn_reflns_theta_max 33.16 _reflns_number_total 15293 _reflns_number_gt 8260 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'SMART software (Siemens, 1995)' _computing_cell_refinement 'SMART software (Siemens, 1995)' _computing_data_reduction 'SAINT software (Siemens, 1995)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP (Johnson, 1976)' _publ_section_exptl_refinement ; 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. All hydrogen atoms in the cyclopeptide were constrained. The hydrogen atoms of the solvate water molecule could not be located. ; _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^)+(0.0740P)^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_abs_structure_details 'Flack, H. D. (1983). Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.1(7) _refine_ls_number_reflns 15293 _refine_ls_number_parameters 553 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1317 _refine_ls_R_factor_gt 0.0595 _refine_ls_wR_factor_ref 0.1438 _refine_ls_wR_factor_gt 0.1229 _refine_ls_goodness_of_fit_ref 0.978 _refine_ls_restrained_S_all 0.978 _refine_ls_shift/su_max 0.001 _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 0.06419(17) 0.58943(12) 0.29082(12) 0.0345(4) Uani 1 1 d . . . C2 C 0.11669(17) 0.51863(11) 0.25501(13) 0.0363(5) Uani 1 1 d . . . H2 H 0.0736 0.4951 0.2168 0.044 Uiso 1 1 calc R . . C3 C 0.1467(2) 0.45764(14) 0.31397(15) 0.0495(6) Uani 1 1 d . . . H3A H 0.1055 0.4109 0.3100 0.059 Uiso 1 1 calc R . . H3B H 0.1403 0.4789 0.3636 0.059 Uiso 1 1 calc R . . C4 C 0.2602(2) 0.44002(15) 0.29443(16) 0.0518(6) Uani 1 1 d . . . H4A H 0.2970 0.4217 0.3376 0.062 Uiso 1 1 calc R . . H4B H 0.2653 0.4012 0.2554 0.062 Uiso 1 1 calc R . . C5 C 0.2985(2) 0.51649(14) 0.26929(15) 0.0497(6) Uani 1 1 d . . . H5A H 0.3112 0.5514 0.3106 0.060 Uiso 1 1 calc R . . H5B H 0.3598 0.5110 0.2401 0.060 Uiso 1 1 calc R . . C6 C 0.21805(17) 0.59028(12) 0.16456(13) 0.0368(5) Uani 1 1 d . . . C7 C 0.31808(16) 0.62704(12) 0.14650(13) 0.0381(5) Uani 1 1 d . . . C8 C 0.36929(18) 0.60932(14) 0.08074(15) 0.0475(6) Uani 1 1 d . . . H8 H 0.3458 0.5699 0.0497 0.057 Uiso 1 1 calc R . . C9 C 0.45499(17) 0.65112(15) 0.06252(14) 0.0454(6) Uani 1 1 d . . . H9 H 0.4900 0.6389 0.0194 0.054 Uiso 1 1 calc R . . C10 C 0.48999(16) 0.71170(13) 0.10804(12) 0.0366(5) Uani 1 1 d . . . C11 C 0.43797(15) 0.72943(12) 0.17432(11) 0.0325(4) Uani 1 1 d . . . C12 C 0.35247(15) 0.68552(12) 0.19372(12) 0.0343(5) Uani 1 1 d . . . H12 H 0.3189 0.6955 0.2380 0.041 Uiso 1 1 calc R . . C13 C 0.44358(17) 0.81211(12) 0.28826(12) 0.0341(4) Uani 1 1 d . . . C14 C 0.50013(15) 0.88222(11) 0.31924(12) 0.0320(4) Uani 1 1 d . . . H14 H 0.5469 0.9037 0.2823 0.038 Uiso 1 1 calc R . . C15 C 0.55700(17) 0.85983(14) 0.39128(13) 0.0432(5) Uani 1 1 d . . . H15A H 0.5499 0.8043 0.4013 0.052 Uiso 1 1 calc R . . H15B H 0.6284 0.8721 0.3869 0.052 Uiso 1 1 calc R . . C16 C 0.5090(2) 0.90768(15) 0.45289(14) 0.0485(6) Uani 1 1 d . . . H16A H 0.4982 0.8756 0.4965 0.058 Uiso 1 1 calc R . . H16B H 0.5522 0.9513 0.4663 0.058 Uiso 1 1 calc R . . C17 C 0.40949(18) 0.93676(14) 0.42280(12) 0.0402(5) Uani 1 1 d . . . H17A H 0.3552 0.9006 0.4343 0.048 Uiso 1 1 calc R . . H17B H 0.3929 0.9878 0.4430 0.048 Uiso 1 1 calc R . . C18 C 0.38835(15) 0.99234(11) 0.29214(11) 0.0303(4) Uani 1 1 d . . . C19 C 0.30432(15) 1.04510(11) 0.31648(11) 0.0283(4) Uani 1 1 d . . . C20 C 0.30467(16) 1.12280(11) 0.29365(11) 0.0318(4) Uani 1 1 d . . . H20 H 0.3583 1.1423 0.2659 0.038 Uiso 1 1 calc R . . C21 C 0.22441(15) 1.17088(12) 0.31272(11) 0.0314(4) Uani 1 1 d . . . H21 H 0.2246 1.2230 0.2978 0.038 Uiso 1 1 calc R . . C22 C 0.14352(15) 1.14213(11) 0.35388(11) 0.0300(4) Uani 1 1 d . . . C23 C 0.14059(15) 1.06246(11) 0.37427(11) 0.0284(4) Uani 1 1 d . . . C24 C 0.22217(15) 1.01459(11) 0.35542(11) 0.0291(4) Uani 1 1 d . . . H24 H 0.2217 0.9621 0.3689 0.035 Uiso 1 1 calc R . . C25 C 0.03698(15) 0.95937(11) 0.43631(11) 0.0285(4) Uani 1 1 d . . . C26 C -0.06690(16) 0.95126(12) 0.47373(13) 0.0357(5) Uani 1 1 d . . . H26 H -0.1160 0.9875 0.4519 0.043 Uiso 1 1 calc R . . C27 C -0.0578(2) 0.96399(15) 0.55791(14) 0.0537(7) Uani 1 1 d . . . H27A H -0.0031 0.9998 0.5694 0.064 Uiso 1 1 calc R . . H27B H -0.1203 0.9846 0.5783 0.064 Uiso 1 1 calc R . . C28 C -0.03596(19) 0.88323(14) 0.58803(14) 0.0457(6) Uani 1 1 d . . . H28A H -0.0550 0.8795 0.6398 0.055 Uiso 1 1 calc R . . H28B H 0.0352 0.8705 0.5831 0.055 Uiso 1 1 calc R . . C29 C -0.10023(19) 0.82955(12) 0.54082(12) 0.0384(5) Uani 1 1 d . . . H29A H -0.0697 0.7782 0.5365 0.046 Uiso 1 1 calc R . . H29B H -0.1677 0.8241 0.5613 0.046 Uiso 1 1 calc R . . C30 C -0.11566(15) 0.83798(11) 0.40109(11) 0.0302(4) Uani 1 1 d . . . C31 C -0.14140(15) 0.75185(11) 0.39775(11) 0.0300(4) Uani 1 1 d . . . C32 C -0.22253(15) 0.71998(11) 0.43679(12) 0.0325(4) Uani 1 1 d . . . H32 H -0.2620 0.7510 0.4677 0.039 Uiso 1 1 calc R . . C33 C -0.24297(15) 0.64037(12) 0.42830(12) 0.0323(4) Uani 1 1 d . . . H33 H -0.2983 0.6188 0.4527 0.039 Uiso 1 1 calc R . . C34 C -0.18282(16) 0.59263(11) 0.38430(11) 0.0304(4) Uani 1 1 d . . . C35 C -0.09950(16) 0.62552(11) 0.34683(11) 0.0313(4) Uani 1 1 d . . . C36 C -0.08150(16) 0.70580(11) 0.35252(11) 0.0327(4) Uani 1 1 d . . . H36 H -0.0290 0.7284 0.3258 0.039 Uiso 1 1 calc R . . C37 C 0.57859(16) 0.75895(14) 0.08389(12) 0.0386(5) Uani 1 1 d . . . C38 C 0.71927(18) 0.77204(15) 0.00697(15) 0.0479(6) Uani 1 1 d . . . H38A H 0.6913 0.8144 -0.0213 0.072 Uiso 1 1 calc R . . H38B H 0.7630 0.7414 -0.0240 0.072 Uiso 1 1 calc R . . H38C H 0.7572 0.7927 0.0479 0.072 Uiso 1 1 calc R . . C39 C 0.06093(16) 1.19641(11) 0.37745(12) 0.0314(4) Uani 1 1 d . . . C40 C -0.05147(19) 1.29497(14) 0.33587(15) 0.0481(6) Uani 1 1 d . . . H40A H -0.1100 1.2640 0.3474 0.072 Uiso 1 1 calc R . . H40B H -0.0649 1.3262 0.2928 0.072 Uiso 1 1 calc R . . H40C H -0.0360 1.3285 0.3770 0.072 Uiso 1 1 calc R . . C41 C -0.20798(16) 0.50807(12) 0.37754(13) 0.0343(5) Uani 1 1 d . . . C42 C -0.3145(2) 0.40546(13) 0.41538(17) 0.0557(7) Uani 1 1 d . . . H42A H -0.3494 0.3994 0.3691 0.084 Uiso 1 1 calc R . . H42B H -0.3593 0.3924 0.4554 0.084 Uiso 1 1 calc R . . H42C H -0.2569 0.3714 0.4164 0.084 Uiso 1 1 calc R . . N1 N -0.03565(13) 0.57734(10) 0.30405(10) 0.0349(4) Uani 1 1 d . . . H1 H -0.0625 0.5364 0.2845 0.042 Uiso 1 1 calc R . . N2 N 0.21316(13) 0.54354(10) 0.22378(11) 0.0365(4) Uani 1 1 d . . . N3 N 0.47365(13) 0.79069(10) 0.21857(10) 0.0337(4) Uani 1 1 d . . . H3 H 0.5209 0.8187 0.1994 0.040 Uiso 1 1 calc R . . N4 N 0.42650(13) 0.94126(10) 0.34248(9) 0.0315(4) Uani 1 1 d . . . N5 N 0.05327(12) 1.03329(9) 0.40968(10) 0.0306(4) Uani 1 1 d . . . H5 H 0.0043 1.0659 0.4152 0.037 Uiso 1 1 calc R . . N6 N -0.10262(12) 0.86996(9) 0.46835(10) 0.0308(4) Uani 1 1 d . . . O1 O 0.11173(12) 0.64763(9) 0.30813(10) 0.0490(4) Uani 1 1 d . . . O2 O 0.14271(12) 0.60574(9) 0.12736(10) 0.0487(4) Uani 1 1 d . . . O3 O 0.37781(16) 0.77937(11) 0.32324(10) 0.0599(5) Uani 1 1 d . . . O4 O 0.42055(12) 0.99424(9) 0.22848(8) 0.0414(4) Uani 1 1 d . . . O5 O 0.09883(11) 0.90666(8) 0.43498(8) 0.0324(3) Uani 1 1 d . . . O6 O -0.10445(13) 0.87601(8) 0.34388(9) 0.0421(4) Uani 1 1 d . . . O7 O -0.16676(13) 0.46246(9) 0.33450(10) 0.0470(4) Uani 1 1 d . . . O8 O -0.28130(12) 0.48590(8) 0.42335(9) 0.0397(4) Uani 1 1 d . . . O9 O 0.59682(13) 0.82412(11) 0.10668(10) 0.0529(4) Uani 1 1 d . . . O10 O 0.63708(11) 0.72260(9) 0.03506(9) 0.0414(4) Uani 1 1 d . . . O11 O 0.02453(11) 1.19885(9) 0.43868(9) 0.0387(4) Uani 1 1 d . . . O12 O 0.03352(12) 1.24408(8) 0.32150(9) 0.0397(4) Uani 1 1 d . . . O13 O 0.11418(19) 0.73766(14) 0.44521(13) 0.0824(7) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0354(11) 0.0291(10) 0.0391(11) -0.0045(8) -0.0040(9) 0.0007(9) C2 0.0359(12) 0.0273(10) 0.0457(12) -0.0055(8) -0.0078(10) 0.0014(9) C3 0.0566(15) 0.0380(12) 0.0538(15) 0.0011(11) -0.0114(12) 0.0027(11) C4 0.0504(15) 0.0495(14) 0.0553(16) 0.0057(12) -0.0124(12) 0.0040(11) C5 0.0430(14) 0.0474(13) 0.0587(16) -0.0017(11) -0.0214(12) 0.0059(11) C6 0.0312(11) 0.0302(10) 0.0490(13) -0.0062(9) -0.0081(10) 0.0019(9) C7 0.0255(10) 0.0379(11) 0.0507(14) -0.0030(10) -0.0071(9) 0.0027(9) C8 0.0287(11) 0.0508(14) 0.0629(16) -0.0175(12) -0.0085(11) 0.0010(10) C9 0.0282(11) 0.0584(14) 0.0496(14) -0.0157(11) -0.0031(10) 0.0070(10) C10 0.0237(10) 0.0440(12) 0.0420(12) -0.0032(9) -0.0033(9) 0.0053(9) C11 0.0258(10) 0.0332(10) 0.0385(11) 0.0009(8) -0.0046(8) 0.0058(8) C12 0.0269(10) 0.0338(10) 0.0420(12) -0.0006(9) -0.0041(9) 0.0043(8) C13 0.0350(11) 0.0312(10) 0.0360(11) 0.0048(8) 0.0033(9) -0.0004(9) C14 0.0259(10) 0.0337(10) 0.0365(11) 0.0022(8) 0.0063(8) -0.0014(8) C15 0.0291(11) 0.0485(13) 0.0520(14) 0.0004(11) -0.0045(10) -0.0004(10) C16 0.0552(15) 0.0443(13) 0.0461(14) 0.0025(11) -0.0114(11) 0.0076(11) C17 0.0454(13) 0.0435(12) 0.0317(11) 0.0010(9) 0.0008(10) 0.0034(10) C18 0.0240(10) 0.0332(10) 0.0337(11) 0.0012(8) 0.0024(8) -0.0062(8) C19 0.0264(10) 0.0320(9) 0.0265(10) -0.0010(7) -0.0014(8) -0.0028(8) C20 0.0284(11) 0.0351(11) 0.0318(11) 0.0001(8) 0.0006(8) -0.0070(8) C21 0.0317(11) 0.0295(10) 0.0330(11) -0.0009(8) -0.0012(8) -0.0058(8) C22 0.0281(10) 0.0294(9) 0.0325(10) -0.0006(8) -0.0032(8) -0.0021(8) C23 0.0253(10) 0.0321(10) 0.0277(10) -0.0017(8) -0.0005(8) -0.0049(8) C24 0.0274(10) 0.0269(9) 0.0329(10) 0.0002(8) 0.0018(8) -0.0023(8) C25 0.0256(10) 0.0303(10) 0.0295(10) -0.0026(8) 0.0011(8) -0.0036(8) C26 0.0294(11) 0.0286(10) 0.0492(13) -0.0036(9) 0.0123(9) -0.0030(8) C27 0.0655(17) 0.0465(13) 0.0492(14) -0.0142(11) 0.0273(13) -0.0183(12) C28 0.0394(13) 0.0601(15) 0.0376(13) -0.0092(11) 0.0057(10) -0.0055(11) C29 0.0435(13) 0.0334(10) 0.0381(11) 0.0049(8) 0.0017(10) -0.0018(9) C30 0.0238(10) 0.0265(9) 0.0403(11) 0.0037(8) 0.0017(8) 0.0007(7) C31 0.0303(10) 0.0260(9) 0.0335(11) 0.0044(8) -0.0052(8) -0.0009(8) C32 0.0256(10) 0.0286(10) 0.0434(12) 0.0055(8) -0.0026(9) 0.0017(8) C33 0.0267(10) 0.0327(10) 0.0374(11) 0.0083(9) -0.0038(8) -0.0040(8) C34 0.0318(11) 0.0255(9) 0.0340(10) 0.0038(8) -0.0072(8) -0.0012(8) C35 0.0322(11) 0.0299(9) 0.0318(10) 0.0053(8) -0.0048(9) 0.0007(8) C36 0.0341(11) 0.0272(9) 0.0367(11) 0.0071(8) 0.0004(9) -0.0038(8) C37 0.0288(11) 0.0512(13) 0.0357(11) -0.0015(10) 0.0004(9) 0.0060(9) C38 0.0305(12) 0.0601(16) 0.0532(15) -0.0032(12) 0.0131(11) 0.0068(11) C39 0.0277(10) 0.0249(9) 0.0417(12) -0.0046(8) -0.0012(9) -0.0065(8) C40 0.0423(14) 0.0352(11) 0.0667(17) 0.0037(11) 0.0025(12) 0.0080(10) C41 0.0312(11) 0.0308(10) 0.0411(12) 0.0089(9) -0.0056(9) -0.0036(9) C42 0.0645(17) 0.0303(11) 0.0724(18) 0.0071(11) 0.0184(15) -0.0104(11) N1 0.0362(10) 0.0270(8) 0.0415(10) -0.0030(7) -0.0005(8) -0.0043(7) N2 0.0253(9) 0.0366(9) 0.0476(11) -0.0091(8) -0.0091(8) 0.0039(7) N3 0.0265(9) 0.0355(9) 0.0390(10) 0.0005(7) 0.0030(7) -0.0015(7) N4 0.0266(9) 0.0341(8) 0.0336(9) -0.0012(7) 0.0052(7) -0.0010(7) N5 0.0242(8) 0.0272(8) 0.0404(10) -0.0026(7) 0.0050(7) -0.0004(6) N6 0.0260(8) 0.0253(8) 0.0413(10) 0.0026(7) 0.0075(7) -0.0019(7) O1 0.0358(9) 0.0364(8) 0.0747(12) -0.0200(8) 0.0032(8) -0.0031(7) O2 0.0292(8) 0.0476(9) 0.0695(11) 0.0141(8) -0.0157(8) -0.0052(7) O3 0.0753(13) 0.0622(11) 0.0422(9) -0.0041(8) 0.0186(9) -0.0387(10) O4 0.0442(9) 0.0451(8) 0.0349(8) 0.0058(6) 0.0126(7) 0.0055(7) O5 0.0279(7) 0.0316(7) 0.0377(8) 0.0042(6) 0.0043(6) 0.0004(6) O6 0.0543(10) 0.0280(7) 0.0439(9) 0.0113(6) -0.0024(8) -0.0024(7) O7 0.0458(10) 0.0287(8) 0.0666(11) -0.0029(7) 0.0096(8) -0.0032(7) O8 0.0468(9) 0.0289(7) 0.0434(9) 0.0049(6) 0.0009(7) -0.0103(6) O9 0.0453(10) 0.0587(10) 0.0549(10) -0.0176(8) 0.0202(8) -0.0137(8) O10 0.0283(8) 0.0508(9) 0.0452(9) -0.0041(7) 0.0030(7) 0.0103(7) O11 0.0348(8) 0.0389(8) 0.0425(9) -0.0023(7) 0.0071(7) 0.0021(6) O12 0.0404(9) 0.0345(7) 0.0444(9) 0.0048(7) 0.0056(7) 0.0073(7) O13 0.0834(16) 0.0794(15) 0.0844(16) 0.0003(12) -0.0184(13) -0.0057(13) _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 O1 1.218(3) . y C1 N1 1.357(3) . y C1 C2 1.538(3) . y C2 N2 1.458(3) . y C2 C3 1.542(3) . y C3 C4 1.571(4) . y C4 C5 1.474(4) . y C5 N2 1.470(3) . y C6 O2 1.230(3) . y C6 N2 1.336(3) . y C6 C7 1.500(3) . y C7 C12 1.390(3) . y C7 C8 1.399(4) . y C8 C9 1.379(4) . y C9 C10 1.400(3) . y C10 C11 1.412(3) . y C10 C37 1.488(3) . y C11 N3 1.399(3) . y C11 C12 1.401(3) . y C13 O3 1.211(3) . y C13 N3 1.369(3) . y C13 C14 1.519(3) . y C14 N4 1.464(3) . y C14 C15 1.550(3) . y C15 C16 1.519(4) . y C16 C17 1.507(3) . y C17 N4 1.469(3) . y C18 O4 1.225(2) . y C18 N4 1.357(3) . y C18 C19 1.497(3) . y C19 C20 1.391(3) . y C19 C24 1.395(3) . y C20 C21 1.386(3) . y C21 C22 1.392(3) . y C22 C23 1.411(3) . y C22 C39 1.495(3) . y C23 C24 1.396(3) . y C23 N5 1.411(2) . y C25 O5 1.217(2) . y C25 N5 1.369(3) . y C25 C26 1.537(3) . y C26 N6 1.471(3) . y C26 C27 1.539(3) . y C27 C28 1.512(4) . y C28 C29 1.513(3) . y C29 N6 1.479(3) . y C30 O6 1.229(2) . y C30 N6 1.342(3) . y C30 C31 1.513(3) . y C31 C36 1.383(3) . y C31 C32 1.394(3) . y C32 C33 1.396(3) . y C33 C34 1.389(3) . y C34 C35 1.410(3) . y C34 C41 1.488(3) . y C35 C36 1.397(3) . y C35 N1 1.410(3) . y C37 O9 1.212(3) . y C37 O10 1.327(3) . y C38 O10 1.467(3) . y C39 O11 1.206(3) . y C39 O12 1.347(3) . y C40 O12 1.445(3) . y C41 O7 1.228(3) . y C41 O8 1.329(3) . y C42 O8 1.451(3) . y 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 O1 C1 N1 125.6(2) . . y O1 C1 C2 121.2(2) . . y N1 C1 C2 113.15(17) . . y N2 C2 C1 109.12(17) . . y N2 C2 C3 103.83(18) . . y C1 C2 C3 111.02(19) . . y C2 C3 C4 102.8(2) . . y C5 C4 C3 103.2(2) . . y N2 C5 C4 100.8(2) . . y O2 C6 N2 121.7(2) . . y O2 C6 C7 120.4(2) . . y N2 C6 C7 117.85(19) . . y C12 C7 C8 121.1(2) . . y C12 C7 C6 117.2(2) . . y C8 C7 C6 121.3(2) . . y C9 C8 C7 119.2(2) . . y C8 C9 C10 121.0(2) . . y C9 C10 C11 119.6(2) . . y C9 C10 C37 119.3(2) . . y C11 C10 C37 120.97(19) . . y N3 C11 C12 122.04(19) . . y N3 C11 C10 118.67(19) . . y C12 C11 C10 119.3(2) . . y C7 C12 C11 119.7(2) . . y O3 C13 N3 124.3(2) . . y O3 C13 C14 121.7(2) . . y N3 C13 C14 113.96(18) . . y N4 C14 C13 108.79(16) . . y N4 C14 C15 104.65(17) . . y C13 C14 C15 110.64(18) . . y C16 C15 C14 106.13(18) . . y C17 C16 C15 106.2(2) . . y N4 C17 C16 103.82(19) . . y O4 C18 N4 121.01(19) . . y O4 C18 C19 121.12(18) . . y N4 C18 C19 117.86(17) . . y C20 C19 C24 120.59(18) . . y C20 C19 C18 119.09(18) . . y C24 C19 C18 120.02(17) . . y C21 C20 C19 119.38(19) . . y C20 C21 C22 120.76(19) . . y C21 C22 C23 120.07(19) . . y C21 C22 C39 119.60(18) . . y C23 C22 C39 120.32(18) . . y C24 C23 N5 122.38(17) . . y C24 C23 C22 118.75(18) . . y N5 C23 C22 118.79(18) . . y C19 C24 C23 120.34(17) . . y O5 C25 N5 124.81(18) . . y O5 C25 C26 122.85(18) . . y N5 C25 C26 112.22(17) . . y N6 C26 C25 110.08(16) . . y N6 C26 C27 102.94(17) . . y C25 C26 C27 110.53(19) . . y C28 C27 C26 103.92(18) . . y C27 C28 C29 104.1(2) . . y N6 C29 C28 103.08(17) . . y O6 C30 N6 121.90(17) . . y O6 C30 C31 120.57(18) . . y N6 C30 C31 117.49(17) . . y C36 C31 C32 121.08(18) . . y C36 C31 C30 116.67(18) . . y C32 C31 C30 122.24(19) . . y C31 C32 C33 118.3(2) . . y C34 C33 C32 121.65(19) . . y C33 C34 C35 119.16(18) . . y C33 C34 C41 119.32(19) . . y C35 C34 C41 121.53(19) . . y C36 C35 C34 119.34(19) . . y C36 C35 N1 120.83(18) . . y C34 C35 N1 119.83(17) . . y C31 C36 C35 120.34(19) . . y O9 C37 O10 122.7(2) . . y O9 C37 C10 123.8(2) . . y O10 C37 C10 113.5(2) . . y O11 C39 O12 123.94(19) . . y O11 C39 C22 125.02(19) . . y O12 C39 C22 111.03(17) . . y O7 C41 O8 122.40(18) . . y O7 C41 C34 124.7(2) . . y O8 C41 C34 112.89(19) . . y C1 N1 C35 126.14(17) . . y C6 N2 C2 121.75(17) . . y C6 N2 C5 126.7(2) . . y C2 N2 C5 111.35(19) . . y C13 N3 C11 128.80(18) . . y C18 N4 C14 119.96(17) . . y C18 N4 C17 129.58(18) . . y C14 N4 C17 110.39(17) . . y C25 N5 C23 127.88(17) . . y C30 N6 C26 119.07(17) . . y C30 N6 C29 127.71(16) . . y C26 N6 C29 112.09(17) . . y C41 O8 C42 115.44(18) . . y C37 O10 C38 113.03(18) . . y C39 O12 C40 116.05(18) . . y _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 33.16 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.649 _refine_diff_density_min -0.486 _refine_diff_density_rms 0.052 #===END ############################################################################ # # # This Supplementary Material is written in the Crystallographic # # Information File (CIF) format. For further details see: S.R. Hall, # # F.H. Allen and I.D. Brown, Acta Cryst. (1991) A47, 655-685. # # # ############################################################################ data_2.acetone ############################################################################ # # _publ_requested_journal 'Chemical Communications' _publ_section_title ; Intramolecular conformational control in a cyclic peptide composed of alternating (L)-proline and substituted 3-aminobenzoic acid subunits ; loop_ _publ_author_name _publ_author_address 'Stefan Kubik' ; Institut f\"ur Organische und Makromolekulare Chemie Heinrich-Heine-Universit\"at Universit\"atsstrasse 1 D-40225 D\"usseldorf Germany ; 'Richard Goddard' ; Max-Planck-Institut f\"ur Kohlenforschung Kaiser-Wilhelm-Platz 1 D-45470 M\"ulheim an der Ruhr Germany ; # # ############################################################################ _chemical_name_systematic ; cyclo-tris[(L)-prolyl-alpha-3-amino-4(methoxycarbonyl)-benzoyl] acetone solvate ; _chemical_name_common 'cyclo[(L)Pro-AMB]~3~ acetone solvate' _chemical_compound_source 'see paper' _chemical_formula_moiety 'C42 H42 N6 O12, C3 H6 O' _chemical_formula_sum 'C45 H48 N6 O13' _chemical_formula_weight 880.89 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 orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' _symmetry_Int_Tables_number 19 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 10.5607(6) _cell_length_b 17.6047(10) _cell_length_c 22.7991(13) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 4238.8(4) _cell_formula_units_Z 4 _cell_measurement_temperature 100 _cell_measurement_reflns_used 8192 _cell_measurement_theta_min 1.46 _cell_measurement_theta_max 34.12 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.64 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.17 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.380 _exptl_crystal_density_method none _exptl_crystal_F_000 1856 _exptl_absorpt_coefficient_mu 0.103 _exptl_absorpt_correction_type none _publ_section_exptl_prep ; The crystal was mounted on a glass fibre and cooled by a stream of nitrogen gas. ; _diffrn_ambient_temperature 100 _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 'Siemens SMART' _diffrn_measurement_method 'CCD \w-scan' _diffrn_standards_number 0 _diffrn_standards_decay_% 0.00 _diffrn_reflns_number 48668 _diffrn_reflns_av_R_equivalents 0.1004 _diffrn_reflns_av_sigmaI/netI 0.1429 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 27 _diffrn_reflns_limit_l_min -35 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 1.46 _diffrn_reflns_theta_max 34.12 _reflns_number_total 16532 _reflns_number_gt 9124 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'SMART software (Siemens, 1995)' _computing_cell_refinement 'SMART software (Siemens, 1995)' _computing_data_reduction 'SAINT software (Siemens, 1995)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP (Johnson, 1976)' _publ_section_exptl_refinement ; 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. Maximum residual difference density 1.175 e/\%A^3^, 2.557 \%A from O7. Attempts to refine the peak as an O atom (solvent water?) were unsuccessful since the adp became very large and the atom moved to another position in the unit cell. The maximum residual difference density remained at its original position. Since the distance to the closest atom is unreasonably short for a hydrogen bond, it was concluded that the maximum residual difference density does not represent an additional solvent molecule. ; _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^)+(0.0851P)^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_abs_structure_details 'Flack, H. D. (1983). Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.3(8) _refine_ls_number_reflns 16532 _refine_ls_number_parameters 582 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1511 _refine_ls_R_factor_gt 0.0730 _refine_ls_wR_factor_ref 0.1715 _refine_ls_wR_factor_gt 0.1439 _refine_ls_goodness_of_fit_ref 0.949 _refine_ls_restrained_S_all 0.949 _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 1.0331(2) 0.36803(13) 0.25341(10) 0.0197(5) Uani 1 1 d . . . C2 C 1.1357(2) 0.42948(12) 0.25000(10) 0.0187(5) Uani 1 1 d . . . H2 H 1.1651 0.4365 0.2096 0.022 Uiso 1 1 calc R . . C3 C 1.2472(2) 0.41417(14) 0.29173(10) 0.0224(5) Uani 1 1 d . . . H3A H 1.2256 0.3751 0.3200 0.027 Uiso 1 1 calc R . . H3B H 1.3216 0.3982 0.2700 0.027 Uiso 1 1 calc R . . C4 C 1.2705(2) 0.49009(14) 0.32237(10) 0.0214(5) Uani 1 1 d . . . H4A H 1.3102 0.4829 0.3603 0.026 Uiso 1 1 calc R . . H4B H 1.3231 0.5232 0.2986 0.026 Uiso 1 1 calc R . . C5 C 1.1373(2) 0.52175(15) 0.32873(10) 0.0233(5) Uani 1 1 d . . . H5A H 1.0937 0.4993 0.3619 0.028 Uiso 1 1 calc R . . H5B H 1.1383 0.5765 0.3332 0.028 Uiso 1 1 calc R . . C6 C 0.9900(2) 0.53643(13) 0.24154(10) 0.0203(5) Uani 1 1 d . . . C7 C 0.9128(2) 0.59564(13) 0.27246(10) 0.0188(5) Uani 1 1 d . . . C8 C 0.8739(2) 0.66064(13) 0.24227(10) 0.0209(5) Uani 1 1 d . . . H8 H 0.9002 0.6691 0.2039 0.025 Uiso 1 1 calc R . . C9 C 0.7963(2) 0.71183(13) 0.26993(10) 0.0195(5) Uani 1 1 d . . . H9 H 0.7711 0.7555 0.2501 0.023 Uiso 1 1 calc R . . C10 C 0.7541(2) 0.69975(12) 0.32748(10) 0.0179(5) Uani 1 1 d . . . C11 C 0.7874(2) 0.63207(13) 0.35677(10) 0.0176(4) Uani 1 1 d . . . C12 C 0.8691(2) 0.58143(13) 0.32922(10) 0.0181(5) Uani 1 1 d . . . H12 H 0.8948 0.5377 0.3488 0.022 Uiso 1 1 calc R . . C13 C 0.7809(2) 0.56834(13) 0.45473(10) 0.0207(5) Uani 1 1 d . . . C14 C 0.6969(2) 0.56711(13) 0.50992(9) 0.0201(5) Uani 1 1 d . . . H14 H 0.6578 0.6170 0.5159 0.024 Uiso 1 1 calc R . . C15 C 0.7680(3) 0.54269(15) 0.56524(11) 0.0298(6) Uani 1 1 d . . . H15A H 0.7337 0.5677 0.5997 0.036 Uiso 1 1 calc R . . H15B H 0.8574 0.5547 0.5621 0.036 Uiso 1 1 calc R . . C16 C 0.7475(3) 0.45709(15) 0.56843(12) 0.0328(6) Uani 1 1 d . . . H16A H 0.8072 0.4305 0.5435 0.039 Uiso 1 1 calc R . . H16B H 0.7569 0.4389 0.6084 0.039 Uiso 1 1 calc R . . C17 C 0.6148(3) 0.44606(15) 0.54719(12) 0.0323(6) Uani 1 1 d . . . H17A H 0.6046 0.3967 0.5289 0.039 Uiso 1 1 calc R . . H17B H 0.5546 0.4508 0.5791 0.039 Uiso 1 1 calc R . . C18 C 0.4885(2) 0.52488(13) 0.47582(9) 0.0193(5) Uani 1 1 d . . . C19 C 0.3930(2) 0.46281(13) 0.46969(9) 0.0190(5) Uani 1 1 d . . . C20 C 0.2653(2) 0.47734(14) 0.47912(9) 0.0219(5) Uani 1 1 d . . . H20 H 0.2397 0.5241 0.4939 0.026 Uiso 1 1 calc R . . C21 C 0.1765(2) 0.42229(14) 0.46660(10) 0.0219(5) Uani 1 1 d . . . H21 H 0.0914 0.4318 0.4738 0.026 Uiso 1 1 calc R . . C22 C 0.2136(2) 0.35132(13) 0.44283(9) 0.0198(5) Uani 1 1 d . . . C23 C 0.3427(2) 0.33777(13) 0.43161(10) 0.0181(5) Uani 1 1 d . . . C24 C 0.4317(2) 0.39311(13) 0.44662(10) 0.0180(5) Uani 1 1 d . . . H24 H 0.5175 0.3835 0.4412 0.022 Uiso 1 1 calc R . . C25 C 0.5000(2) 0.24908(13) 0.38678(11) 0.0225(5) Uani 1 1 d . . . C26 C 0.5045(2) 0.17583(13) 0.34957(10) 0.0206(5) Uani 1 1 d . . . H26 H 0.4225 0.1657 0.3310 0.025 Uiso 1 1 calc R . . C27 C 0.5479(3) 0.10800(14) 0.38727(12) 0.0261(5) Uani 1 1 d . . . H27A H 0.5240 0.1151 0.4280 0.031 Uiso 1 1 calc R . . H27B H 0.5110 0.0610 0.3731 0.031 Uiso 1 1 calc R . . C28 C 0.6915(3) 0.10687(14) 0.38067(11) 0.0252(5) Uani 1 1 d . . . H28A H 0.7254 0.0566 0.3883 0.030 Uiso 1 1 calc R . . H28B H 0.7313 0.1429 0.4071 0.030 Uiso 1 1 calc R . . C29 C 0.7112(2) 0.12978(14) 0.31660(11) 0.0243(5) Uani 1 1 d . . . H29A H 0.7921 0.1549 0.3112 0.029 Uiso 1 1 calc R . . H29B H 0.7069 0.0860 0.2909 0.029 Uiso 1 1 calc R . . C30 C 0.5897(2) 0.22814(13) 0.25912(11) 0.0225(5) Uani 1 1 d . . . C31 C 0.6969(2) 0.23210(14) 0.21548(11) 0.0224(5) Uani 1 1 d . . . C32 C 0.6854(2) 0.20050(14) 0.15935(11) 0.0245(5) Uani 1 1 d . . . H32 H 0.6141 0.1723 0.1493 0.029 Uiso 1 1 calc R . . C33 C 0.7809(2) 0.21165(13) 0.11925(11) 0.0239(5) Uani 1 1 d . . . H33 H 0.7755 0.1884 0.0827 0.029 Uiso 1 1 calc R . . C34 C 0.8862(2) 0.25731(14) 0.13216(10) 0.0209(5) Uani 1 1 d . . . C35 C 0.8958(2) 0.28987(13) 0.18882(10) 0.0206(5) Uani 1 1 d . . . C36 C 0.8017(2) 0.27484(14) 0.22986(10) 0.0222(5) Uani 1 1 d . . . H36 H 0.8097 0.2940 0.2677 0.027 Uiso 1 1 calc R . . C37 C 0.6746(2) 0.75774(13) 0.35679(10) 0.0193(5) Uani 1 1 d . . . C38 C 0.6124(3) 0.88509(14) 0.36000(13) 0.0320(6) Uani 1 1 d . . . H38A H 0.5257 0.8687 0.3594 0.048 Uiso 1 1 calc R . . H38B H 0.6206 0.9312 0.3378 0.048 Uiso 1 1 calc R . . H38C H 0.6382 0.8940 0.3998 0.048 Uiso 1 1 calc R . . C39 C 0.1137(3) 0.29494(14) 0.42796(10) 0.0240(5) Uani 1 1 d . . . C40 C -0.1043(3) 0.26736(18) 0.42916(13) 0.0346(6) Uani 1 1 d . . . H40A H -0.1096 0.2657 0.3871 0.052 Uiso 1 1 calc R . . H40B H -0.1821 0.2871 0.4448 0.052 Uiso 1 1 calc R . . H40C H -0.0904 0.2171 0.4441 0.052 Uiso 1 1 calc R . . C41 C 0.9855(2) 0.27158(15) 0.08743(10) 0.0237(5) Uani 1 1 d . . . C42 C 1.0792(3) 0.23324(16) -0.00134(11) 0.0296(6) Uani 1 1 d . . . H42A H 1.0656 0.2816 -0.0198 0.044 Uiso 1 1 calc R . . H42B H 1.0737 0.1937 -0.0302 0.044 Uiso 1 1 calc R . . H42C H 1.1617 0.2325 0.0164 0.044 Uiso 1 1 calc R . . C43 C 0.6031(3) 0.49934(16) 0.26834(12) 0.0304(6) Uani 1 1 d . . . C44 C 0.6060(4) 0.4625(2) 0.32838(12) 0.0494(9) Uani 1 1 d . . . H44A H 0.5918 0.5004 0.3579 0.074 Uiso 1 1 calc R . . H44B H 0.6871 0.4392 0.3346 0.074 Uiso 1 1 calc R . . H44C H 0.5409 0.4246 0.3307 0.074 Uiso 1 1 calc R . . C45 C 0.6678(4) 0.45549(19) 0.22166(15) 0.0505(9) Uani 1 1 d . . . H45A H 0.6607 0.4821 0.1851 0.076 Uiso 1 1 calc R . . H45B H 0.6291 0.4064 0.2181 0.076 Uiso 1 1 calc R . . H45C H 0.7556 0.4495 0.2316 0.076 Uiso 1 1 calc R . . N1 N 0.99601(19) 0.34027(11) 0.20089(8) 0.0210(4) Uani 1 1 d . . . H1 H 1.0391 0.3553 0.1710 0.025 Uiso 1 1 calc R . . N2 N 1.07865(19) 0.49929(10) 0.27310(8) 0.0187(4) Uani 1 1 d . . . N3 N 0.73605(19) 0.61655(11) 0.41254(8) 0.0188(4) Uani 1 1 d . . . H3 H 0.6676 0.6405 0.4212 0.023 Uiso 1 1 calc R . . N4 N 0.5984(2) 0.50840(11) 0.50369(8) 0.0206(4) Uani 1 1 d . . . N5 N 0.37972(19) 0.27029(11) 0.40261(8) 0.0199(4) Uani 1 1 d . . . H5 H 0.3200 0.2390 0.3939 0.024 Uiso 1 1 calc R . . N6 N 0.6052(2) 0.18228(11) 0.30579(9) 0.0207(4) Uani 1 1 d . . . O1 O 0.9900(2) 0.34922(11) 0.30064(8) 0.0369(5) Uani 1 1 d . . . O2 O 0.96650(19) 0.51957(11) 0.18997(7) 0.0316(4) Uani 1 1 d . . . O3 O 0.87669(19) 0.53041(11) 0.45046(8) 0.0329(4) Uani 1 1 d . . . O4 O 0.46937(17) 0.58686(9) 0.45203(7) 0.0235(4) Uani 1 1 d . . . O5 O 0.59568(18) 0.28221(11) 0.40031(10) 0.0395(5) Uani 1 1 d . . . O6 O 0.49553(18) 0.26822(10) 0.25333(9) 0.0316(4) Uani 1 1 d . . . O7 O 1.06241(19) 0.32333(12) 0.08874(8) 0.0349(5) Uani 1 1 d . . . O8 O 0.98380(18) 0.22121(10) 0.04332(7) 0.0271(4) Uani 1 1 d . . . O9 O 0.60379(18) 0.74589(10) 0.39797(8) 0.0297(4) Uani 1 1 d . . . O10 O 0.69087(16) 0.82752(9) 0.33463(7) 0.0217(4) Uani 1 1 d . . . O11 O 0.13292(17) 0.23544(10) 0.40155(8) 0.0294(4) Uani 1 1 d . . . O12 O 0.00028(17) 0.31633(11) 0.44652(8) 0.0297(4) Uani 1 1 d . . . O13 O 0.5509(2) 0.55644(13) 0.25749(10) 0.0499(6) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0226(12) 0.0177(11) 0.0187(11) -0.0031(9) 0.0019(10) 0.0011(9) C2 0.0227(12) 0.0187(11) 0.0148(10) -0.0016(8) 0.0028(9) 0.0027(9) C3 0.0223(12) 0.0239(12) 0.0209(12) -0.0022(10) -0.0022(10) 0.0022(10) C4 0.0224(12) 0.0261(12) 0.0156(11) -0.0013(9) -0.0031(9) -0.0012(10) C5 0.0248(12) 0.0275(13) 0.0177(11) -0.0065(9) -0.0040(10) 0.0013(11) C6 0.0264(12) 0.0191(11) 0.0153(11) 0.0006(8) 0.0029(10) 0.0004(10) C7 0.0205(12) 0.0178(11) 0.0183(11) 0.0005(9) -0.0003(9) 0.0007(9) C8 0.0261(12) 0.0214(11) 0.0150(11) 0.0026(9) 0.0003(10) 0.0002(10) C9 0.0236(12) 0.0176(11) 0.0174(11) 0.0036(8) -0.0006(10) -0.0008(10) C10 0.0200(11) 0.0151(11) 0.0186(11) 0.0020(8) 0.0004(9) 0.0001(9) C11 0.0183(11) 0.0199(11) 0.0146(10) 0.0015(8) -0.0005(9) -0.0006(9) C12 0.0194(11) 0.0164(10) 0.0184(11) 0.0015(9) -0.0008(9) -0.0011(9) C13 0.0264(13) 0.0163(11) 0.0193(11) -0.0001(9) -0.0011(10) -0.0016(10) C14 0.0283(13) 0.0200(12) 0.0121(10) 0.0006(8) -0.0027(9) -0.0050(10) C15 0.0399(16) 0.0312(14) 0.0184(12) 0.0026(10) -0.0057(11) -0.0079(12) C16 0.0381(16) 0.0306(14) 0.0298(14) 0.0121(11) -0.0105(12) -0.0072(13) C17 0.0400(16) 0.0288(13) 0.0280(14) 0.0155(11) -0.0091(13) -0.0090(12) C18 0.0271(12) 0.0206(11) 0.0103(10) -0.0011(8) 0.0046(9) 0.0010(10) C19 0.0254(12) 0.0202(11) 0.0115(10) 0.0008(8) 0.0008(9) 0.0000(10) C20 0.0289(13) 0.0239(12) 0.0130(10) -0.0005(9) 0.0029(9) 0.0006(11) C21 0.0236(12) 0.0293(13) 0.0127(10) 0.0037(9) 0.0040(9) 0.0027(10) C22 0.0238(12) 0.0239(12) 0.0117(10) 0.0026(9) -0.0008(9) -0.0026(10) C23 0.0197(11) 0.0208(11) 0.0137(10) 0.0014(9) 0.0004(9) 0.0013(9) C24 0.0186(11) 0.0195(11) 0.0158(11) 0.0027(8) -0.0003(9) -0.0006(9) C25 0.0214(12) 0.0217(11) 0.0244(12) -0.0031(9) -0.0005(10) -0.0015(10) C26 0.0218(12) 0.0192(11) 0.0208(11) -0.0031(9) -0.0004(10) -0.0027(10) C27 0.0325(14) 0.0192(12) 0.0266(13) 0.0014(10) -0.0005(11) -0.0037(10) C28 0.0312(14) 0.0217(12) 0.0225(12) 0.0024(9) -0.0042(11) 0.0006(11) C29 0.0257(12) 0.0229(12) 0.0244(12) 0.0009(10) 0.0007(11) 0.0062(11) C30 0.0229(12) 0.0187(11) 0.0260(12) 0.0012(9) -0.0045(10) -0.0036(10) C31 0.0246(13) 0.0187(11) 0.0240(12) 0.0042(9) -0.0038(10) 0.0037(10) C32 0.0233(12) 0.0232(12) 0.0272(13) 0.0021(10) -0.0060(11) 0.0007(10) C33 0.0296(13) 0.0222(12) 0.0198(11) -0.0016(9) -0.0070(11) 0.0039(10) C34 0.0241(12) 0.0228(12) 0.0158(11) 0.0007(9) -0.0036(10) 0.0032(10) C35 0.0220(11) 0.0210(11) 0.0187(11) -0.0001(9) -0.0019(10) 0.0037(10) C36 0.0256(12) 0.0254(12) 0.0157(11) 0.0021(9) -0.0020(10) 0.0032(10) C37 0.0193(11) 0.0182(11) 0.0202(11) 0.0007(9) -0.0013(9) -0.0020(9) C38 0.0403(16) 0.0189(12) 0.0368(15) -0.0019(11) 0.0107(13) 0.0063(12) C39 0.0251(13) 0.0262(13) 0.0206(12) 0.0044(10) 0.0004(10) -0.0028(11) C40 0.0190(12) 0.0500(17) 0.0348(15) 0.0051(13) -0.0009(12) -0.0092(13) C41 0.0252(13) 0.0310(13) 0.0149(11) 0.0000(9) -0.0068(10) 0.0074(11) C42 0.0408(16) 0.0324(14) 0.0157(11) 0.0000(10) 0.0016(11) 0.0090(12) C43 0.0256(13) 0.0345(15) 0.0310(14) 0.0012(11) 0.0023(11) -0.0048(12) C44 0.059(2) 0.067(2) 0.0223(14) 0.0048(14) -0.0002(15) -0.0337(19) C45 0.061(2) 0.0450(18) 0.0453(19) -0.0047(15) 0.0146(18) 0.0046(17) N1 0.0202(10) 0.0284(10) 0.0146(9) -0.0021(8) -0.0015(8) -0.0034(9) N2 0.0225(10) 0.0172(9) 0.0165(9) -0.0041(7) 0.0001(8) 0.0020(8) N3 0.0199(10) 0.0211(10) 0.0154(9) 0.0014(7) 0.0025(8) 0.0008(8) N4 0.0263(11) 0.0196(9) 0.0159(9) 0.0042(7) -0.0019(8) -0.0057(9) N5 0.0210(10) 0.0160(9) 0.0227(10) -0.0027(8) -0.0002(8) -0.0041(8) N6 0.0224(10) 0.0185(9) 0.0211(10) -0.0007(8) 0.0007(8) 0.0013(8) O1 0.0535(13) 0.0409(11) 0.0165(9) -0.0038(8) 0.0056(9) -0.0223(10) O2 0.0443(12) 0.0343(10) 0.0162(8) -0.0040(7) -0.0042(8) 0.0169(9) O3 0.0358(11) 0.0382(11) 0.0247(9) 0.0095(8) 0.0039(8) 0.0118(9) O4 0.0294(9) 0.0179(8) 0.0231(9) -0.0005(7) 0.0003(8) 0.0017(7) O5 0.0238(9) 0.0326(10) 0.0622(14) -0.0240(10) -0.0005(10) -0.0014(9) O6 0.0251(9) 0.0323(10) 0.0373(10) 0.0113(8) 0.0022(8) 0.0057(8) O7 0.0382(11) 0.0480(12) 0.0185(9) -0.0070(8) 0.0025(8) -0.0095(10) O8 0.0362(10) 0.0264(9) 0.0188(8) -0.0021(7) 0.0030(8) 0.0052(8) O9 0.0329(10) 0.0254(9) 0.0310(10) 0.0057(7) 0.0124(9) 0.0059(8) O10 0.0251(9) 0.0156(8) 0.0244(8) 0.0003(6) 0.0047(7) 0.0023(7) O11 0.0263(10) 0.0271(9) 0.0346(10) -0.0026(8) 0.0005(8) -0.0054(8) O12 0.0197(9) 0.0380(10) 0.0315(10) -0.0015(8) 0.0016(8) -0.0050(8) O13 0.0465(13) 0.0462(13) 0.0570(15) 0.0253(11) -0.0029(11) 0.0004(11) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O1 1.215(3) . y C1 N1 1.351(3) . y C1 C2 1.533(3) . y C2 N2 1.466(3) . y C2 C3 1.538(3) . y C3 C4 1.528(3) . y C4 C5 1.520(3) . y C5 N2 1.466(3) . y C6 O2 1.238(3) . y C6 N2 1.350(3) . y C6 C7 1.499(3) . y C7 C12 1.397(3) . y C7 C8 1.397(3) . y C8 C9 1.372(3) . y C9 C10 1.402(3) . y C10 C11 1.411(3) . y C10 C37 1.481(3) . y C11 C12 1.390(3) . y C11 N3 1.409(3) . y C13 O3 1.216(3) . y C13 N3 1.368(3) . y C13 C14 1.540(3) . y C14 N4 1.474(3) . y C14 C15 1.529(3) . y C15 C16 1.524(4) . y C16 C17 1.495(4) . y C17 N4 1.489(3) . y C18 O4 1.235(3) . y C18 N4 1.354(3) . y C18 C19 1.494(3) . y C19 C20 1.389(4) . y C19 C24 1.396(3) . y C20 C21 1.378(4) . y C21 C22 1.417(3) . y C22 C23 1.408(3) . y C22 C39 1.488(3) . y C23 C24 1.396(3) . y C23 N5 1.415(3) . y C25 O5 1.207(3) . y C25 N5 1.372(3) . y C25 C26 1.544(3) . y C26 N6 1.464(3) . y C26 C27 1.541(3) . y C27 C28 1.524(4) . y C28 C29 1.530(3) . y C29 N6 1.472(3) . y C30 O6 1.226(3) . y C30 N6 1.346(3) . y C30 C31 1.509(4) . y C31 C36 1.378(4) . y C31 C32 1.401(4) . y C32 C33 1.375(4) . y C33 C34 1.404(4) . y C34 C35 1.417(3) . y C34 C41 1.484(4) . y C35 C36 1.390(3) . y C35 N1 1.408(3) . y C37 O9 1.218(3) . y C37 O10 1.339(3) . y C38 O10 1.431(3) . y C39 O11 1.225(3) . y C39 O12 1.325(3) . y C40 O12 1.456(3) . y C41 O7 1.221(3) . y C41 O8 1.341(3) . y C42 O8 1.448(3) . y C43 O13 1.173(3) . y C43 C45 1.482(4) . y C43 C44 1.515(4) . y 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 O1 C1 N1 125.3(2) . . y O1 C1 C2 120.1(2) . . y N1 C1 C2 114.5(2) . . y N2 C2 C1 106.44(18) . . y N2 C2 C3 103.83(18) . . y C1 C2 C3 112.72(19) . . y C4 C3 C2 104.66(19) . . y C5 C4 C3 102.4(2) . . y N2 C5 C4 102.09(18) . . y O2 C6 N2 122.0(2) . . y O2 C6 C7 120.3(2) . . y N2 C6 C7 117.60(19) . . y C12 C7 C8 120.4(2) . . y C12 C7 C6 119.4(2) . . y C8 C7 C6 119.9(2) . . y C9 C8 C7 119.2(2) . . y C8 C9 C10 121.4(2) . . y C9 C10 C11 119.4(2) . . y C9 C10 C37 119.9(2) . . y C11 C10 C37 120.7(2) . . y C12 C11 C10 118.9(2) . . y C12 C11 N3 121.5(2) . . y C10 C11 N3 119.6(2) . . y C11 C12 C7 120.6(2) . . y O3 C13 N3 125.0(2) . . y O3 C13 C14 122.5(2) . . y N3 C13 C14 112.6(2) . . y N4 C14 C15 103.24(18) . . y N4 C14 C13 109.76(18) . . y C15 C14 C13 113.3(2) . . y C14 C15 C16 104.3(2) . . y C17 C16 C15 104.3(2) . . y N4 C17 C16 103.2(2) . . y O4 C18 N4 122.4(2) . . y O4 C18 C19 119.6(2) . . y N4 C18 C19 117.77(19) . . y C20 C19 C24 120.3(2) . . y C20 C19 C18 120.4(2) . . y C24 C19 C18 118.7(2) . . y C21 C20 C19 119.9(2) . . y C20 C21 C22 120.8(2) . . y C23 C22 C21 119.1(2) . . y C23 C22 C39 122.2(2) . . y C21 C22 C39 118.7(2) . . y C24 C23 C22 119.3(2) . . y C24 C23 N5 121.0(2) . . y C22 C23 N5 119.6(2) . . y C23 C24 C19 120.5(2) . . y O5 C25 N5 125.2(2) . . y O5 C25 C26 121.2(2) . . y N5 C25 C26 113.6(2) . . y N6 C26 C27 102.94(19) . . y N6 C26 C25 109.41(19) . . y C27 C26 C25 110.5(2) . . y C28 C27 C26 104.6(2) . . y C27 C28 C29 103.1(2) . . y N6 C29 C28 102.8(2) . . y O6 C30 N6 122.0(2) . . y O6 C30 C31 120.7(2) . . y N6 C30 C31 117.2(2) . . y C36 C31 C32 120.3(2) . . y C36 C31 C30 118.1(2) . . y C32 C31 C30 121.3(2) . . y C33 C32 C31 119.2(2) . . y C32 C33 C34 121.6(2) . . y C33 C34 C35 118.6(2) . . y C33 C34 C41 120.8(2) . . y C35 C34 C41 120.5(2) . . y C36 C35 N1 121.7(2) . . y C36 C35 C34 119.1(2) . . y N1 C35 C34 119.1(2) . . y C31 C36 C35 121.2(2) . . y O9 C37 O10 121.8(2) . . y O9 C37 C10 125.3(2) . . y O10 C37 C10 112.93(19) . . y O11 C39 O12 123.4(2) . . y O11 C39 C22 124.4(2) . . y O12 C39 C22 112.3(2) . . y O7 C41 O8 121.4(2) . . y O7 C41 C34 125.4(2) . . y O8 C41 C34 113.2(2) . . y O13 C43 C45 120.8(3) . . y O13 C43 C44 124.5(3) . . y C45 C43 C44 114.6(3) . . y C1 N1 C35 128.2(2) . . y C6 N2 C2 119.96(19) . . y C6 N2 C5 128.58(19) . . y C2 N2 C5 111.31(18) . . y C13 N3 C11 128.4(2) . . y C18 N4 C14 120.01(19) . . y C18 N4 C17 124.8(2) . . y C14 N4 C17 111.73(19) . . y C25 N5 C23 127.4(2) . . y C30 N6 C26 119.8(2) . . y C30 N6 C29 127.0(2) . . y C26 N6 C29 112.94(18) . . y C41 O8 C42 114.9(2) . . y C37 O10 C38 115.01(19) . . y C39 O12 C40 115.5(2) . . y _diffrn_measured_fraction_theta_max 0.969 _diffrn_reflns_theta_full 34.12 _diffrn_measured_fraction_theta_full 0.969 _refine_diff_density_max 1.175 _refine_diff_density_min -0.361 _refine_diff_density_rms 0.072 #===END