# Supplementary Material (ESI) for Perkin Transactions 1 # This journal is © The Royal Society of Chemistry 2002 data_global _journal_coden_Cambridge 207 _publ_requested_journal 'Perkin Transactions 1' loop_ _publ_author_name 'Fleet, George' 'Long, Daniel D.' 'Martin, Angeles' 'Muller, Mattaius' 'Smith, Martin D.' 'Watkin, David G.' 'Wheatley, Joseph R.' _publ_contact_author_name 'Dr George Fleet' _publ_contact_author_address ; Dyson Perrins Oxford University South Parks Road oxford Oxon OX1 3QY UNITED KINGDOM ; _publ_contact_author_email 'GEORGE.FLEET@SJC.OX.AC.UK' _publ_section_title ; Complex tetrahydrofurans from carbohydrate lactones: THF amino acids as building blocks for unnatural biopolymers ; _publ_section_references ; Altomare, A., Cascarano, G., Giacovazzo G., Guagliardi A., Burla M.C., Polidori, G. & Camalli, M. (1994) SIR92 - a program for automatic solution of crystal structures by direct methods. J. Appl. Cryst. (27), 435-435 Enraf-Nonius, (1989) Cad4 Express. Watkin, D.J., Prout, C.K., Carruthers, J.R., Betteridge, P.W. & Cooper R.I. (2001) CRYSTALS Issue 11. Chemical Crystallography Laboratory, OXFORD, UK. Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996) CAMERON, Chemical Crystallography Laboratory, OXFORD, UK. Watkin, D.J., Prout, C.K., Lilley, P.M.deQ. (1994), RC93, Chemical Crystallography Laboratory, Oxford, UK. ; data_1 _database_code_CSD 182246 _audit_creation_date 02-19-03 _audit_creation_method CRYSTALS_ver_12-03-99 _chemical_name_systematic # IUPAC name, in full ; ? ; _chemical_melting_point 'not measured' # choose from 'full, fullcycle, atomblock, userblock, diagonal, sparse' _refine_ls_matrix_type full # choose from 'heavy, direct, difmap, geom' _atom_sites_solution_primary direct # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom # choose from 'none, undef, noref, refall, refxyz, refU, constr, mixed' _refine_ls_hydrogen_treatment noref #**************************************************************************** # General computing #============================================================= _computing_structure_refinement ; CRYSTALS (Watkin et al 2001) ; _computing_publication_material ; CRYSTALS (Watkin et al 2001) ; _computing_molecular_graphics ; CAMERON (Watkin et al 1996) ; #============================================================= _cell_length_a 7.147(1) _cell_angle_alpha 90 _cell_length_b 6.349(1) _cell_angle_beta 106.03(2) _cell_length_c 11.384(1) _cell_angle_gamma 90 _cell_volume 496.46(12) _symmetry_cell_setting 'Monoclinic ' _symmetry_space_group_name_H-M 'P 1 21 1 ' loop_ _symmetry_equiv_pos_as_xyz 'x,y,z' '-x,y+1/2,-z' loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source 'C ' 0.0181 0.0091 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International_Tables_Vol_IV_Table_2.2B' 'H ' 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7997 0.0030 'International_Tables_Vol_IV_Table_2.2B' 'N ' 0.0311 0.0180 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 'International_Tables_Vol_IV_Table_2.2B' 'O ' 0.0492 0.0322 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 'International_Tables_Vol_IV_Table_2.2B' _chemical_formula_sum ' C7 H12 N4 O5 ' _chemical_formula_moiety ' C7 H12 N4 O5 ' _chemical_compound_source ; ? ; _chemical_formula_weight 232.20 _cell_measurement_reflns_used 24 _cell_measurement_theta_min 30 _cell_measurement_theta_max 32 _cell_measurement_temperature 293 _cell_formula_units_Z 2 _exptl_crystal_description ' prism ' _exptl_crystal_colour ' colourless ' _exptl_crystal_size_min 0.32 _exptl_crystal_size_mid 0.60 _exptl_crystal_size_max 0.60 _exptl_crystal_density_diffrn 1.553 _exptl_crystal_density_meas 'not measured' _exptl_crystal_F_000 244.933 _exptl_absorpt_coefficient_mu 1.148 # Sheldrick geometric definitions 0.50 0.69 _diffrn_measurement_device_type ; Enraf-Nonius Mach3 ; _diffrn_radiation_monochromator graphite _computing_data_collection ; Cad4 Express, (Enraf-Nonius, 1989) ; _computing_data_reduction ; RC93 (Watkin, Prout & Lilley, 1994) ; _computing_cell_refinement ; Cad4 Express, (Enraf-Nonius, 1989) ; _computing_structure_solution ; SIR92 (Altomare et al, 1994) ; _diffrn_measurement_method \w/2\q _exptl_absorpt_correction_type psi-scan _exptl_absorpt_correction_T_min 0.50 _exptl_absorpt_correction_T_max 0.69 _diffrn_standards_interval_time 0 _diffrn_standards_interval_count 0 _diffrn_standards_number 3 _diffrn_standards_decay_% 1.67 _diffrn_ambient_temperature 293 _diffrn_reflns_number 3127 _reflns_number_total 1978 _diffrn_reflns_av_R_equivalents 0.02 # Number of reflections with Friedels Law is 1978 # Number of reflections without Friedels Law is 1978 # Theoretical number of reflections is about 1006 _diffrn_measured_fraction_theta_max 1.000 _reflns_number_gt 1973 _diffrn_reflns_theta_min 4.04 _diffrn_reflns_theta_max 73.90 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _reflns_limit_h_min -8 _reflns_limit_h_max 8 _reflns_limit_k_min -7 _reflns_limit_k_max 7 _reflns_limit_l_min 0 _reflns_limit_l_max 14 _refine_diff_density_min -0.29 _refine_diff_density_max 0.26 _reflns_threshold_expression >3.00\s(I) _refine_ls_number_reflns 1973 _refine_ls_number_parameters 168 _refine_ls_R_factor_gt 0.0275 _refine_ls_wR_factor_ref 0.0230 _refine_ls_goodness_of_fit_ref 0.9856 _refine_ls_shift/su_max 0.005875 _refine_ls_abs_structure_Flack 0.00(14) _refine_ls_abs_structure_details 'Flack, 0 Friedel-pairs' _refine_ls_structure_factor_coef F _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method= Tukey and Prince W = [weight] * [1-(deltaF/6*sigmaF)^2]^2 3.54 -0.501 0.941 ; _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54180 # Uequiv = arithmetic mean of Ui # i.e. Ueqiv = (U1+U2+U3)/3 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_occupancy _atom_site_adp_type O1 O 0.08366(11) 0.05556(14) 0.16457(7) 0.0305 1.0000 Uani O25 O 0.45451(13) 0.18978(18) 0.43103(8) 0.0478 1.0000 Uani O31 O 0.28044(12) -0.25885(16) 0.35219(7) 0.0398 1.0000 Uani O41 O 0.33617(11) -0.25712(16) 0.04909(8) 0.0370 1.0000 Uani O52 O -0.28685(11) -0.09666(15) 0.10562(9) 0.0363 1.0000 Uani N21 N 0.38496(14) 0.18431(18) 0.16656(9) 0.0338 1.0000 Uani N22 N 0.54246(15) 0.26038(19) 0.2214(1) 0.0391 1.0000 Uani N23 N 0.6871(2) 0.3391(3) 0.25809(15) 0.0705 1.0000 Uani N26 N 0.12769(15) 0.2312(2) 0.3816(1) 0.0388 1.0000 Uani C2 C 0.27582(15) 0.06207(19) 0.23770(9) 0.0257 1.0000 Uani C3 C 0.34401(16) -0.16857(19) 0.2569(1) 0.0283 1.0000 Uani C4 C 0.22956(15) -0.27345(19) 0.1375(1) 0.0273 1.0000 Uani C5 C 0.04071(14) -0.14498(18) 0.10110(9) 0.0239 1.0000 Uani C24 C 0.29088(17) 0.17000(19) 0.3604(1) 0.0312 1.0000 Uani C27 C 0.1257(3) 0.3314(3) 0.49635(15) 0.0552 1.0000 Uani C51 C -0.13012(15) -0.2427(2) 0.1347(1) 0.0305 1.0000 Uani H31 H 0.4755(13) -0.180(2) 0.2653(12) 0.0270 1.0000 Uiso H41 H 0.2050(18) -0.4105(14) 0.1540(11) 0.0260 1.0000 Uiso H51 H 0.0102(18) -0.1157(19) 0.0197(8) 0.0230 1.0000 Uiso H261 H 0.0194(15) 0.210(3) 0.322(1) 0.0380 1.0000 Uiso H311 H 0.3763(16) -0.255(3) 0.4199(9) 0.0360 1.0000 Uiso H411 H 0.307(2) -0.3747(17) 0.0052(12) 0.0330 1.0000 Uiso H521 H -0.3964(15) -0.172(2) 0.0906(12) 0.0330 1.0000 Uiso H271 H -0.0114 0.3660 0.4949 0.0583 1.0000 Uiso H272 H 0.1826 0.2332 0.5657 0.0583 1.0000 Uiso H273 H 0.2045 0.4637 0.5072 0.0583 1.0000 Uiso H511 H -0.0934 -0.2748 0.2241 0.0303 1.0000 Uiso H512 H -0.1697 -0.3757 0.0872 0.0303 1.0000 Uiso 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 0.0205(4) 0.0274(4) 0.0372(4) -0.0045(3) -0.0028(3) 0.0002(3) O25 0.0388(5) 0.0646(7) 0.0325(4) -0.0144(4) -0.0024(4) -0.0027(4) O31 0.0391(4) 0.0435(5) 0.0305(4) 0.0123(4) -0.0010(3) -0.0047(4) O41 0.0273(4) 0.0434(5) 0.0436(4) -0.0147(4) 0.0155(3) -0.0066(4) O52 0.0216(4) 0.0363(5) 0.0526(5) -0.0005(4) 0.0130(4) -0.0017(3) N21 0.0316(5) 0.0371(6) 0.0313(5) 0.0019(4) 0.0064(4) -0.0074(4) N22 0.0319(5) 0.0408(6) 0.0456(6) -0.0032(5) 0.0126(4) -0.0082(5) N23 0.0462(8) 0.0896(11) 0.076(1) -0.0115(9) 0.0170(7) -0.0340(8) N26 0.0377(5) 0.0402(6) 0.0409(5) -0.0083(5) 0.0148(4) -0.0019(5) C2 0.0200(5) 0.0281(6) 0.0263(5) -0.0006(4) 0.0021(4) -0.0022(4) C3 0.0219(5) 0.0303(6) 0.0292(5) 0.0031(4) 0.0014(4) 0.0018(4) C4 0.0223(5) 0.0267(6) 0.0321(5) -0.0028(5) 0.0062(4) -0.0006(4) C5 0.0216(5) 0.0271(6) 0.0214(5) -0.0018(4) 0.0031(4) -0.0020(4) C24 0.0326(6) 0.0311(6) 0.0288(5) -0.0020(5) 0.0065(4) -0.0036(5) C27 0.0640(9) 0.0548(9) 0.0564(9) -0.0157(7) 0.0327(8) -0.0073(8) C51 0.0242(5) 0.0312(6) 0.0369(5) -0.0000(5) 0.0099(4) -0.0031(5) _refine_ls_extinction_coef 12.7(8) _refine_ls_extinction_method 'Larson 1970 Crystallographic Computing eq 22' loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag O1 . C2 . 1.3963(12) yes O1 . C5 . 1.4541(13) yes O25 . C24 . 1.2292(14) yes O31 . C3 . 1.4085(14) yes O41 . C4 . 1.4240(13) yes O52 . C51 . 1.4211(15) yes N21 . N22 . 1.2256(14) yes N21 . C2 . 1.4884(14) yes N22 . N23 . 1.1202(17) yes N26 . C24 . 1.3135(16) yes N26 . C27 . 1.4566(18) yes C2 . C3 . 1.5396(16) yes C2 . C24 . 1.5324(15) yes C3 . C4 . 1.5316(15) yes C4 . C5 . 1.5329(15) yes C5 . C51 . 1.5097(14) yes loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C2 . O1 . C5 . 111.11(8) yes N22 . N21 . C2 . 118.3(1) yes N21 . N22 . N23 . 171.56(15) yes C24 . N26 . C27 . 121.55(12) yes O1 . C2 . N21 . 105.55(8) yes O1 . C2 . C3 . 106.09(9) yes N21 . C2 . C3 . 112.34(9) yes O1 . C2 . C24 . 111.51(9) yes N21 . C2 . C24 . 110.32(9) yes C3 . C2 . C24 . 110.86(9) yes O31 . C3 . C2 . 109.8(1) yes O31 . C3 . C4 . 107.44(9) yes C2 . C3 . C4 . 102.53(8) yes O41 . C4 . C3 . 109.67(8) yes O41 . C4 . C5 . 111.92(9) yes C3 . C4 . C5 . 102.90(9) yes O1 . C5 . C4 . 106.39(8) yes O1 . C5 . C51 . 107.98(9) yes C4 . C5 . C51 . 115.2(1) yes O25 . C24 . N26 . 125.60(11) yes O25 . C24 . C2 . 117.2(1) yes N26 . C24 . C2 . 117.2(1) yes O52 . C51 . C5 . 108.3(1) yes data_2 _database_code_CSD 182247 _audit_creation_date 02-19-03 _audit_creation_method CRYSTALS_ver_12-03-99 # MM36A # Check this file using the IUCr facility at: # http://www/iucr.ac.uk/iucr-top/journals/acta/c/services/checkcif.html #**************************************************************************** # The contents of this file between this point and the next #***** line # are held in the file REFCIF.DAT # This is a character file which you may edit to reflect local conditions # # Items which need looking at are represented by a '?' # Items for which there are choices are prefixed with 'choose from' # # 1. SUBMISSION DETAILS _publ_contact_letter ; Please consider this CIF submission for publication as a Short Format Paper in Acta Crystallographica C. The figures have been sent by mail. ; _publ_contact_author_name 'George Fleet' _publ_contact_author_address ; Dyson Perrins Laboratory South Parks Road OXFORD ; _publ_contact_author_phone ' 01865 ' _publ_contact_author_fax ' 01865 ' _publ_contact_author_email 'george.fleet@chem.ox.ac.uk ' #============================================================================= # 3. TITLE AND AUTHOR LIST _publ_section_title ; Complex tetrahydrofurans from carbohydrate lactones: THF amino acids as building blocks for unnatural biopolymers ; # Daniel D. Long, Martin D. Smith, Angeles Marten, Joseph R. Wheatley, David # J. Watkin, Mattaius Muller, and George W. J. Fleet # Dyson Perrins Laboratory, Oxford University, South Parks Road, Oxford # OX1 3QY, UK; E-mail: gwjf@ermine.ox.ac.uk # Chemical Crystallography Laboratory, Oxford University, 9 Parks Road, # Oxford OX1 3QU, UK #============================================================================== _publ_section_exptl_refinement # see also _refine_ls_hydrogen for refinement keywords. ; H atoms placed geometrically after each cycle ; _publ_section_exptl_prep ; ? ; #========================================================================== _chemical_name_systematic # IUPAC name, in full ; ? ; _chemical_melting_point 'not measured' # choose from 'full, fullcycle, atomblock, userblock, diagonal, sparse' _refine_ls_matrix_type full # choose from 'heavy, direct, difmap, geom' _atom_sites_solution_primary direct # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom # choose from 'none, undef, noref, refall, refxyz, refU, constr, mixed' _refine_ls_hydrogen_treatment noref _vrf_REFLT_03_CRYSTALS_cif ; PROBLEM: Alert A: < 85% complete (theta max?) The material had suffered a 7% decay when data collection was halted. The data was collected in concentric theta-shells, and it was evident that the outer shell contained very few reflections above background at the stopping point. The poor observatio:parameter ratio reflects the poor quality of the crystals ; #**************************************************************************** # General computing #============================================================= _computing_structure_refinement ; CRYSTALS (Watkin et al 2001) ; _computing_publication_material ; CRYSTALS (Watkin et al 2001) ; _computing_molecular_graphics ; CAMERON (Watkin et al 1996) ; #============================================================= _cell_length_a 18.382(2) _cell_angle_alpha 90 _cell_length_b 8.655(1) _cell_angle_beta 102.55(2) _cell_length_c 27.054(4) _cell_angle_gamma 90 _cell_volume 4201.3(10) _symmetry_cell_setting 'Monoclinic ' _symmetry_space_group_name_H-M 'C 1 2 1 ' loop_ _symmetry_equiv_pos_as_xyz 'x,y,z' 'x+1/2,y+1/2,z' '-x,y,-z' '-x+1/2,y+1/2,-z' loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source 'C ' 0.0181 0.0091 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International_Tables_Vol_IV_Table_2.2B' 'H ' 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7997 0.0030 'International_Tables_Vol_IV_Table_2.2B' 'O ' 0.0492 0.0322 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 'International_Tables_Vol_IV_Table_2.2B' 'N ' 0.0311 0.0180 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 'International_Tables_Vol_IV_Table_2.2B' _chemical_formula_sum ' C36 H68 N8 O10 ' _chemical_formula_moiety ' (C18 H34 N4 O5)2 ' _chemical_compound_source ; ? ; _chemical_formula_weight 772.98 _cell_measurement_reflns_used 25 _cell_measurement_theta_min 21 _cell_measurement_theta_max 43 _cell_measurement_temperature 293 _cell_formula_units_Z 4 _exptl_crystal_description ' cube ' _exptl_crystal_colour ' colourless ' _exptl_crystal_size_min 0.10 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_max 0.10 _exptl_crystal_density_diffrn 1.222 _exptl_crystal_density_meas 'not measured' _exptl_crystal_F_000 1685.247 _exptl_absorpt_coefficient_mu 0.734 # Sheldrick geometric definitions 0.93 0.93 _diffrn_measurement_device_type ; Enraf-Nonius Mach3 ; _diffrn_radiation_monochromator graphite _computing_data_collection ; Cad4 Express, (Enraf-Nonius, 1989) ; _computing_data_reduction ; RC93 (Watkin, Prout & Lilley, 1994) ; _computing_cell_refinement ; Cad4 Express, (Enraf-Nonius, 1989) ; _computing_structure_solution ; SIR92 (Altomare et al, 1994) ; _diffrn_measurement_method \w/2\q _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.93 _exptl_absorpt_correction_T_max 0.93 _diffrn_standards_interval_time 0 _diffrn_standards_interval_count 0 _diffrn_standards_number 3 _diffrn_standards_decay_% 7.59 _diffrn_ambient_temperature 293 _diffrn_reflns_number 5716 _reflns_number_total 3762 _diffrn_reflns_av_R_equivalents 0.01 # Number of reflections with Friedels Law is 3762 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 4239 _diffrn_measured_fraction_theta_max 0.888 _reflns_number_gt 3083 _diffrn_reflns_theta_min 3.35 _diffrn_reflns_theta_max 73.59 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 0 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -32 _diffrn_reflns_limit_l_max 33 _reflns_limit_h_min -22 _reflns_limit_h_max 22 _reflns_limit_k_min 0 _reflns_limit_k_max 10 _reflns_limit_l_min 0 _reflns_limit_l_max 33 _refine_diff_density_min -0.58 _refine_diff_density_max 0.47 _reflns_threshold_expression >1.00\s(I) _refine_ls_number_reflns 3083 _refine_ls_number_parameters 487 _refine_ls_R_factor_gt 0.0745 _refine_ls_wR_factor_ref 0.0971 _refine_ls_goodness_of_fit_ref 0.9078 _refine_ls_shift/su_max 0.007513 _refine_ls_structure_factor_coef F _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method= Tukey and Prince W = [weight] * [1-(deltaF/6*sigmaF)^2]^2 3.06 3.10 1.99 ; _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54180 ## -------------------REFERENCES ----------------------## ## Insert your own references - in alphabetic order _publ_section_references ; Altomare, A., Cascarano, G., Giacovazzo G., Guagliardi A., Burla M.C., Polidori, G. & Camalli, M. (1994) SIR92 - a program for automatic solution of crystal structures by direct methods. J. Appl. Cryst. (27), 435-435 Enraf-Nonius, (1989) Cad4 Express. Watkin, D.J., Prout, C.K., Carruthers, J.R., Betteridge, P.W. & Cooper R.I. (2001) CRYSTALS Issue 11. Chemical Crystallography Laboratory, OXFORD, UK. Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996) CAMERON, Chemical Crystallography Laboratory, OXFORD, UK. Watkin, D.J., Prout, C.K., Lilley, P.M.deQ. (1994), RC93, Chemical Crystallography Laboratory, Oxford, UK. ; # Uequiv = arithmetic mean of Ui # i.e. Ueqiv = (U1+U2+U3)/3 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_occupancy _atom_site_adp_type O1 O 0.1891(2) 0.3469(5) 0.40064(14) 0.0158 1.0000 Uani O6 O -0.1072(2) 0.8942(5) 0.35718(15) 0.0155 1.0000 Uani O12 O -0.0888(2) 1.1678(6) 0.41737(17) 0.0241 1.0000 Uani O25 O 0.2110(2) 0.2869(6) 0.29984(17) 0.0249 1.0000 Uani O31 O 0.0063(2) 0.1844(5) 0.35084(15) 0.0183 1.0000 Uani O41 O 0.0324(2) 0.3459(5) 0.45833(15) 0.0189 1.0000 Uani O52 O 0.2393(3) 0.1789(6) 0.49089(17) 0.0238 1.0000 Uani O75 O -0.0227(3) 0.5750(5) 0.31058(16) 0.0225 1.0000 Uani O81 O 0.0177(2) 0.6444(5) 0.43894(15) 0.0181 1.0000 Uani O91 O -0.1162(2) 0.7764(6) 0.48256(15) 0.0231 1.0000 Uani N21 N 0.1531(3) 0.0931(6) 0.36750(19) 0.0152 1.0000 Uani N22 N 0.2188(3) 0.0519(6) 0.37171(19) 0.0156 1.0000 Uani N23 N 0.2754(3) -0.0019(7) 0.3771(2) 0.0300 1.0000 Uani N26 N 0.0945(3) 0.3846(7) 0.28047(18) 0.0211 1.0000 Uani N71 N 0.0183(3) 0.8579(6) 0.36358(19) 0.0167 1.0000 Uani N72 N 0.0741(3) 0.7754(7) 0.3646(2) 0.0231 1.0000 Uani N73 N 0.1303(4) 0.7214(7) 0.3663(3) 0.0311 1.0000 Uani N76 N -0.1424(3) 0.6633(6) 0.29442(19) 0.0191 1.0000 Uani C2 C 0.1394(3) 0.2639(7) 0.3628(2) 0.0156 1.0000 Uani C3 C 0.0632(3) 0.2846(7) 0.37590(19) 0.0125 1.0000 Uani C4 C 0.0854(3) 0.2788(7) 0.4338(2) 0.0156 1.0000 Uani C5 C 0.1566(3) 0.3718(7) 0.4441(2) 0.0136 1.0000 Uani C7 C -0.0528(3) 0.7787(7) 0.3633(2) 0.0155 1.0000 Uani C8 C -0.0531(3) 0.6994(7) 0.4143(2) 0.0147 1.0000 Uani C9 C -0.0818(3) 0.8283(8) 0.4430(2) 0.0202 1.0000 Uani C10 C -0.1392(3) 0.9067(7) 0.4017(2) 0.0159 1.0000 Uani C11 C -0.1540(4) 1.0744(8) 0.4102(2) 0.0215 1.0000 Uani C24 C 0.1515(3) 0.3166(7) 0.3107(2) 0.0145 1.0000 Uani C27 C 0.0957(4) 0.4281(8) 0.2282(2) 0.0228 1.0000 Uani C28 C 0.0176(4) 0.4289(7) 0.1957(2) 0.0181 1.0000 Uani C29 C 0.0158(4) 0.4532(8) 0.1399(2) 0.0212 1.0000 Uani C30 C -0.0628(4) 0.4603(8) 0.1071(2) 0.0236 1.0000 Uani C31 C -0.0650(4) 0.4810(9) 0.0510(3) 0.0292 1.0000 Uani C32 C -0.1442(4) 0.4947(9) 0.0180(2) 0.0263 1.0000 Uani C33 C -0.1440(4) 0.5155(9) -0.0379(2) 0.0258 1.0000 Uani C34 C -0.2214(4) 0.5275(9) -0.0722(2) 0.0239 1.0000 Uani C35 C -0.2206(4) 0.5504(8) -0.1280(2) 0.0229 1.0000 Uani C36 C -0.2988(4) 0.5652(9) -0.1626(2) 0.0268 1.0000 Uani C37 C -0.2972(4) 0.5910(9) -0.2176(2) 0.0279 1.0000 Uani C38 C -0.3754(5) 0.6066(12) -0.2509(3) 0.0431 1.0000 Uani C51 C 0.2125(3) 0.3317(7) 0.4923(2) 0.0167 1.0000 Uani C74 C -0.0728(3) 0.6634(8) 0.3192(2) 0.0192 1.0000 Uani C77 C -0.1732(3) 0.5493(8) 0.2551(2) 0.0227 1.0000 Uani C78 C -0.2063(4) 0.6277(9) 0.2049(2) 0.0254 1.0000 Uani C79 C -0.2438(4) 0.5133(9) 0.1648(2) 0.0254 1.0000 Uani C80 C -0.2818(4) 0.5908(9) 0.1148(2) 0.0277 1.0000 Uani C81 C -0.3206(4) 0.4786(9) 0.0747(2) 0.0267 1.0000 Uani C82 C -0.3606(4) 0.557(1) 0.0259(3) 0.0317 1.0000 Uani C83 C -0.3975(4) 0.445(1) -0.0156(3) 0.0310 1.0000 Uani C84 C -0.4388(4) 0.5221(9) -0.0641(3) 0.0309 1.0000 Uani C85 C -0.4737(4) 0.4076(9) -0.1049(2) 0.0284 1.0000 Uani C86 C -0.5147(4) 0.4868(9) -0.1536(3) 0.0278 1.0000 Uani C87 C -0.5526(4) 0.3753(8) -0.1950(3) 0.0294 1.0000 Uani C88 C -0.5927(4) 0.4572(11) -0.2437(3) 0.0357 1.0000 Uani H31 H 0.0329 0.3767 0.3616 0.0118 1.0000 Uiso H41 H 0.0880 0.1724 0.4484 0.0165 1.0000 Uiso H51 H 0.1444 0.4831 0.4481 0.0142 1.0000 Uiso H81 H -0.0807 0.5994 0.4129 0.0134 1.0000 Uiso H91 H -0.0410 0.8946 0.4626 0.0203 1.0000 Uiso H101 H -0.1888 0.8557 0.3983 0.0150 1.0000 Uiso H111 H -0.1754 1.0831 0.4411 0.0215 1.0000 Uiso H112 H -0.1908 1.1139 0.3801 0.0215 1.0000 Uiso H271 H 0.1179 0.5336 0.2280 0.0209 1.0000 Uiso H272 H 0.1268 0.3520 0.2140 0.0209 1.0000 Uiso H281 H -0.0112 0.5141 0.2076 0.0177 1.0000 Uiso H282 H -0.0066 0.3275 0.1999 0.0177 1.0000 Uiso H291 H 0.0417 0.5526 0.1359 0.0202 1.0000 Uiso H292 H 0.0429 0.3657 0.1277 0.0202 1.0000 Uiso H301 H -0.0895 0.5492 0.1187 0.0224 1.0000 Uiso H302 H -0.0891 0.3618 0.1116 0.0224 1.0000 Uiso H311 H -0.0370 0.5771 0.0466 0.0268 1.0000 Uiso H312 H -0.0402 0.3899 0.0390 0.0268 1.0000 Uiso H321 H -0.1694 0.5858 0.0297 0.0252 1.0000 Uiso H322 H -0.1726 0.3986 0.0220 0.0252 1.0000 Uiso H331 H -0.1159 0.6122 -0.0417 0.0237 1.0000 Uiso H332 H -0.1179 0.4249 -0.0491 0.0237 1.0000 Uiso H341 H -0.2478 0.6174 -0.0608 0.0228 1.0000 Uiso H342 H -0.2493 0.4303 -0.0688 0.0228 1.0000 Uiso H351 H -0.1920 0.6467 -0.1313 0.0209 1.0000 Uiso H352 H -0.1950 0.4597 -0.1396 0.0209 1.0000 Uiso H361 H -0.3249 0.6546 -0.1506 0.0251 1.0000 Uiso H362 H -0.3272 0.4681 -0.1599 0.0251 1.0000 Uiso H371 H -0.2686 0.6877 -0.2204 0.0251 1.0000 Uiso H372 H -0.2716 0.5013 -0.2298 0.0251 1.0000 Uiso H381 H -0.3716 0.6234 -0.2868 0.0377 1.0000 Uiso H382 H -0.4012 0.6966 -0.2391 0.0377 1.0000 Uiso H383 H -0.4042 0.5101 -0.2485 0.0377 1.0000 Uiso H511 H 0.1879 0.3420 0.5217 0.0152 1.0000 Uiso H512 H 0.2554 0.4050 0.4965 0.0152 1.0000 Uiso H771 H -0.2131 0.4887 0.2663 0.0218 1.0000 Uiso H772 H -0.1325 0.4780 0.2504 0.0218 1.0000 Uiso H781 H -0.2441 0.7053 0.2104 0.0244 1.0000 Uiso H782 H -0.1655 0.6814 0.1925 0.0244 1.0000 Uiso H791 H -0.2824 0.4550 0.1783 0.0220 1.0000 Uiso H792 H -0.2053 0.4398 0.1579 0.0220 1.0000 Uiso H801 H -0.3197 0.6656 0.1220 0.0256 1.0000 Uiso H802 H -0.2430 0.6477 0.1013 0.0256 1.0000 Uiso H811 H -0.3582 0.4188 0.0886 0.0252 1.0000 Uiso H812 H -0.2825 0.4062 0.0665 0.0252 1.0000 Uiso H821 H -0.3999 0.6265 0.0339 0.0304 1.0000 Uiso H822 H -0.3233 0.6201 0.0127 0.0304 1.0000 Uiso H831 H -0.4339 0.3807 -0.0021 0.0293 1.0000 Uiso H832 H -0.3579 0.3775 -0.0241 0.0293 1.0000 Uiso H841 H -0.4793 0.5883 -0.0560 0.0296 1.0000 Uiso H842 H -0.4029 0.5882 -0.0775 0.0296 1.0000 Uiso H851 H -0.5101 0.3419 -0.0917 0.0262 1.0000 Uiso H852 H -0.4335 0.3408 -0.1130 0.0262 1.0000 Uiso H861 H -0.5537 0.5563 -0.1451 0.0268 1.0000 Uiso H862 H -0.4779 0.5499 -0.1672 0.0268 1.0000 Uiso H871 H -0.5901 0.3129 -0.1817 0.0259 1.0000 Uiso H872 H -0.5139 0.3050 -0.2035 0.0259 1.0000 Uiso H881 H -0.6164 0.3785 -0.2693 0.0312 1.0000 Uiso H882 H -0.6321 0.5273 -0.2359 0.0312 1.0000 Uiso H883 H -0.5559 0.5194 -0.2576 0.0312 1.0000 Uiso 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 0.0109(18) 0.023(2) 0.0130(18) -0.0008(17) 0.0012(14) -0.0017(18) O6 0.0126(19) 0.016(2) 0.0185(19) 0.0002(16) 0.0038(15) 0.0075(17) O12 0.025(2) 0.021(2) 0.028(2) -0.003(2) 0.0102(18) -0.009(2) O25 0.020(2) 0.035(3) 0.021(2) 0.004(2) 0.0056(17) 0.004(2) O31 0.015(2) 0.022(2) 0.018(2) -0.0051(17) 0.0040(16) -0.0030(18) O41 0.018(2) 0.025(2) 0.0166(19) -0.0014(18) 0.0090(16) 0.0029(19) O52 0.026(2) 0.018(2) 0.025(2) 0.0055(19) -0.0014(18) 0.004(2) O75 0.026(2) 0.021(2) 0.019(2) -0.0029(18) 0.0021(17) 0.008(2) O81 0.014(2) 0.023(2) 0.0158(19) 0.0016(18) -0.0007(15) 0.0064(18) O91 0.019(2) 0.034(3) 0.017(2) 0.0049(19) 0.0057(16) 0.010(2) N21 0.012(2) 0.015(2) 0.017(2) 0.0013(19) -0.0006(18) 0.001(2) N22 0.014(3) 0.011(2) 0.022(3) 0.0062(19) 0.0055(19) 0.000(2) N23 0.024(3) 0.019(3) 0.047(4) 0.006(3) 0.009(3) 0.008(3) N26 0.023(3) 0.031(3) 0.010(2) 0.006(2) 0.0063(19) 0.008(2) N71 0.011(2) 0.018(3) 0.021(2) 0.005(2) 0.0028(18) 0.005(2) N72 0.016(3) 0.025(3) 0.031(3) 0.006(2) 0.010(2) 0.004(3) N73 0.029(3) 0.018(3) 0.048(4) 0.006(3) 0.014(3) 0.003(3) N76 0.017(2) 0.020(3) 0.017(2) -0.008(2) -0.0011(18) -0.001(2) C2 0.015(3) 0.015(3) 0.016(3) 0.001(2) -0.001(2) 0.001(2) C3 0.009(2) 0.019(3) 0.010(2) 0.006(2) 0.0025(19) 0.003(2) C4 0.018(3) 0.018(3) 0.013(3) 0.004(2) 0.010(2) -0.003(3) C5 0.016(3) 0.013(3) 0.014(2) -0.001(2) 0.007(2) 0.001(2) C7 0.014(3) 0.013(3) 0.018(3) 0.001(2) 0.001(2) 0.005(2) C8 0.012(3) 0.022(3) 0.009(2) -0.005(2) -0.0004(19) -0.001(2) C9 0.016(3) 0.027(3) 0.020(3) 0.007(3) 0.008(2) 0.004(3) C10 0.017(3) 0.013(3) 0.015(3) 0.002(2) -0.002(2) 0.003(2) C11 0.025(3) 0.017(3) 0.023(3) -0.003(3) 0.007(2) 0.001(3) C24 0.014(3) 0.016(3) 0.012(3) 0.001(2) 0.002(2) -0.003(2) C27 0.022(3) 0.034(4) 0.012(3) 0.010(3) 0.003(2) 0.008(3) C28 0.022(3) 0.016(3) 0.015(3) 0.005(2) 0.004(2) -0.002(2) C29 0.028(3) 0.023(3) 0.013(3) 0.004(3) 0.005(2) 0.006(3) C30 0.030(4) 0.026(3) 0.014(3) -0.001(3) 0.005(2) -0.004(3) C31 0.030(4) 0.042(4) 0.015(3) 0.006(3) 0.005(3) -0.002(3) C32 0.028(4) 0.034(4) 0.017(3) 0.002(3) 0.005(3) -0.004(3) C33 0.025(3) 0.038(4) 0.014(3) 0.003(3) 0.003(2) 0.001(3) C34 0.025(3) 0.032(4) 0.015(3) -0.004(3) 0.005(3) -0.005(3) C35 0.027(3) 0.029(4) 0.012(3) -0.000(3) 0.001(2) 0.005(3) C36 0.031(4) 0.031(4) 0.017(3) -0.005(3) 0.001(3) 0.006(3) C37 0.034(4) 0.031(4) 0.015(3) -0.007(3) -0.002(3) 0.009(3) C38 0.045(5) 0.060(6) 0.020(3) -0.010(4) -0.004(3) 0.010(4) C51 0.019(3) 0.010(3) 0.018(3) 0.003(2) -0.001(2) 0.003(2) C74 0.021(3) 0.021(3) 0.016(3) -0.002(2) 0.005(2) 0.003(3) C77 0.021(3) 0.022(3) 0.022(3) -0.005(3) -0.001(2) -0.001(3) C78 0.033(3) 0.032(4) 0.014(3) -0.012(3) 0.010(2) -0.003(3) C79 0.035(4) 0.029(3) 0.010(3) -0.006(3) 0.002(2) 0.001(3) C80 0.028(3) 0.037(4) 0.016(3) -0.003(3) 0.000(2) -0.004(3) C81 0.027(3) 0.031(4) 0.019(3) -0.006(3) -0.001(3) -0.009(3) C82 0.035(4) 0.035(4) 0.022(3) 0.004(3) 0.002(3) -0.008(3) C83 0.037(4) 0.038(4) 0.018(3) 0.003(3) 0.005(3) -0.004(4) C84 0.037(4) 0.031(4) 0.023(3) -0.002(3) 0.001(3) 0.003(3) C85 0.042(4) 0.026(3) 0.016(3) 0.003(3) 0.005(3) 0.003(3) C86 0.028(4) 0.026(4) 0.026(3) -0.001(3) -0.001(3) 0.000(3) C87 0.044(4) 0.015(3) 0.026(3) 0.002(3) 0.002(3) 0.003(3) C88 0.036(4) 0.047(5) 0.018(3) 0.002(3) -0.007(3) -0.002(4) _refine_ls_extinction_method 'None' loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag O1 . C2 . 1.411(7) yes O1 . C5 . 1.446(6) yes O6 . C7 . 1.398(7) yes O6 . C10 . 1.455(7) yes O12 . C11 . 1.424(8) yes O25 . C24 . 1.222(8) yes O31 . C3 . 1.413(7) yes O41 . C4 . 1.418(7) yes O52 . C51 . 1.415(8) yes O75 . C74 . 1.258(8) yes O81 . C8 . 1.409(7) yes O91 . C9 . 1.430(7) yes N21 . N22 . 1.240(7) yes N21 . C2 . 1.499(8) yes N22 . N23 . 1.120(8) yes N26 . C24 . 1.320(8) yes N26 . C27 . 1.469(7) yes N71 . N72 . 1.245(7) yes N71 . C7 . 1.475(8) yes N72 . N73 . 1.125(8) yes N76 . C74 . 1.308(8) yes N76 . C77 . 1.471(8) yes C2 . C3 . 1.529(8) yes C2 . C24 . 1.542(8) yes C3 . C4 . 1.530(8) yes C4 . C5 . 1.509(8) yes C5 . C51 . 1.514(8) yes C7 . C8 . 1.543(8) yes C7 . C74 . 1.536(8) yes C8 . C9 . 1.517(9) yes C9 . C10 . 1.519(8) yes C10 . C11 . 1.504(9) yes C27 . C28 . 1.513(9) yes C28 . C29 . 1.519(8) yes C29 . C30 . 1.523(9) yes C30 . C31 . 1.519(9) yes C31 . C32 . 1.538(9) yes C32 . C33 . 1.523(9) yes C33 . C34 . 1.524(9) yes C34 . C35 . 1.525(8) yes C35 . C36 . 1.540(9) yes C36 . C37 . 1.513(9) yes C37 . C38 . 1.53(1) yes C77 . C78 . 1.522(9) yes C78 . C79 . 1.518(9) yes C79 . C80 . 1.535(9) yes C80 . C81 . 1.515(9) yes C81 . C82 . 1.52(1) yes C82 . C83 . 1.52(1) yes C83 . C84 . 1.52(1) yes C84 . C85 . 1.52(1) yes C85 . C86 . 1.531(9) yes C86 . C87 . 1.53(1) yes C87 . C88 . 1.537(9) yes loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C2 . O1 . C5 . 110.4(4) yes C7 . O6 . C10 . 111.3(4) yes N22 . N21 . C2 . 115.7(5) yes N21 . N22 . N23 . 171.8(6) yes C24 . N26 . C27 . 122.4(5) yes N72 . N71 . C7 . 117.3(5) yes N71 . N72 . N73 . 169.5(7) yes C74 . N76 . C77 . 123.5(5) yes O1 . C2 . N21 . 111.8(5) yes O1 . C2 . C3 . 104.7(5) yes N21 . C2 . C3 . 104.0(5) yes O1 . C2 . C24 . 108.2(5) yes N21 . C2 . C24 . 108.3(5) yes C3 . C2 . C24 . 119.8(5) yes O31 . C3 . C2 . 115.9(5) yes O31 . C3 . C4 . 118.4(5) yes C2 . C3 . C4 . 100.3(4) yes O41 . C4 . C3 . 114.1(5) yes O41 . C4 . C5 . 110.5(5) yes C3 . C4 . C5 . 101.6(4) yes O1 . C5 . C4 . 105.3(4) yes O1 . C5 . C51 . 110.0(5) yes C4 . C5 . C51 . 115.9(5) yes O6 . C7 . N71 . 106.1(5) yes O6 . C7 . C8 . 106.4(5) yes N71 . C7 . C8 . 112.2(5) yes O6 . C7 . C74 . 109.1(5) yes N71 . C7 . C74 . 111.6(5) yes C8 . C7 . C74 . 111.0(5) yes O81 . C8 . C7 . 113.0(5) yes O81 . C8 . C9 . 113.3(4) yes C7 . C8 . C9 . 101.5(5) yes O91 . C9 . C8 . 114.3(6) yes O91 . C9 . C10 . 110.0(5) yes C8 . C9 . C10 . 102.5(5) yes O6 . C10 . C9 . 103.5(5) yes O6 . C10 . C11 . 108.5(5) yes C9 . C10 . C11 . 116.0(5) yes O12 . C11 . C10 . 113.2(5) yes O25 . C24 . N26 . 125.2(5) yes O25 . C24 . C2 . 118.2(5) yes N26 . C24 . C2 . 116.5(5) yes N26 . C27 . C28 . 110.4(5) yes C27 . C28 . C29 . 113.0(5) yes C28 . C29 . C30 . 113.4(5) yes C29 . C30 . C31 . 113.8(5) yes C30 . C31 . C32 . 114.0(6) yes C31 . C32 . C33 . 112.3(5) yes C32 . C33 . C34 . 114.2(6) yes C33 . C34 . C35 . 113.8(5) yes C34 . C35 . C36 . 113.8(6) yes C35 . C36 . C37 . 113.2(6) yes C36 . C37 . C38 . 112.1(6) yes O52 . C51 . C5 . 111.5(5) yes O75 . C74 . N76 . 125.2(6) yes O75 . C74 . C7 . 118.5(5) yes N76 . C74 . C7 . 116.2(5) yes N76 . C77 . C78 . 111.3(5) yes C77 . C78 . C79 . 112.2(6) yes C78 . C79 . C80 . 113.2(6) yes C79 . C80 . C81 . 113.9(6) yes C80 . C81 . C82 . 113.5(6) yes C81 . C82 . C83 . 114.2(7) yes C82 . C83 . C84 . 114.7(7) yes C83 . C84 . C85 . 113.3(6) yes C84 . C85 . C86 . 112.7(6) yes C85 . C86 . C87 . 114.1(6) yes C86 . C87 . C88 . 113.2(6) yes