# Supplementary Material (ESI) for New Journal of Chemistry # This journal is (c) The Royal Society of Chemistry and The Centre National de la Recherche Scientifique, 2010 data_global _journal_name_full 'New J.Chem.' _journal_coden_Cambridge 0440 _publ_contact_author_name 'Aldridge, S.' _publ_contact_author_email simon.aldridge@chem.ox.ac.uk _publ_section_title ; Comparative structural and thermodynamic studies of fluoride and cyanide binding by PhBMes2 and related triarylborane Lewis acids ; loop_ _publ_author_name C.Bresner C.Haynes D.Addy A.Broomsgrove P.Fitzpatrick ; D.Vidovic ; A.Thompson I.Fallis S.Aldridge # Attachment '- Combined structural data.cif' #============================================================================== data_nBu4_1_F _database_code_depnum_ccdc_archive 'CCDC 765939' #TrackingRef '- Combined structural data.cif' #============================================================================== _audit_creation_date 08-05-08 _audit_creation_method CRYSTALS_ver_12.85 _oxford_structure_analysis_title 5816 _chemical_name_systematic . _chemical_melting_point 'not measured' _cell_length_a 10.3016(2) _cell_length_b 19.4960(3) _cell_length_c 18.7092(4) _cell_angle_alpha 90 _cell_angle_beta 94.4224(7) _cell_angle_gamma 90 _cell_volume 3746.37(12) _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 1 21/c 1 ' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z -x,y+1/2,-z+1/2 x,-y+1/2,z+1/2 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 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4' B 0.0013 0.0007 2.0545 23.2185 1.3326 1.0210 1.0979 60.3498 0.7068 0.1403 -0.1932 'International Tables Vol C 4.2.6.8 and 6.1.1.4' F 0.0171 0.0103 3.5392 10.2825 2.6412 4.2944 1.5170 0.2615 1.0243 26.1476 0.2776 'International Tables Vol C 4.2.6.8 and 6.1.1.4' N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 4 # Given Formula = C41 H63 B1 F1 N1 # Dc = 1.06 Fooo = 1296.00 Mu = 0.63 M = 599.77 # Found Formula = C40 H63 B1 F1 N1 # Dc = 1.04 FOOO = 1296.00 Mu = 0.62 M = 587.76 _chemical_formula_sum 'C40 H63 B1 F1 N1' _chemical_formula_moiety 'C24 H27 B F, C16 H36 N' _chemical_compound_source . _chemical_formula_weight 587.76 _cell_measurement_reflns_used 8214 _cell_measurement_theta_min 5 _cell_measurement_theta_max 27 _cell_measurement_temperature 150 _exptl_crystal_description block _exptl_crystal_colour clear_pale_colourless _exptl_crystal_size_min 0.17 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_max 0.55 _exptl_crystal_density_diffrn 1.042 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 1296 _exptl_absorpt_coefficient_mu 0.062 # Sheldrick geometric approximatio 0.98 0.99 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _exptl_absorpt_correction_T_min 0.89 _exptl_absorpt_correction_T_max 0.99 # For a Kappa CCD, set Tmin to 1.0 and # Tmax to the ratio of max:min frame scales in scale_all.log _diffrn_measurement_device 'Nonius KappaCCD' _diffrn_measurement_device_type Area _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method \w # If a reference occurs more than once, delete the author # and date from subsequent references. _computing_data_collection 'COLLECT (Nonius, 1997-2001).' _computing_cell_refinement 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_data_reduction 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _diffrn_standards_interval_time . _diffrn_standards_interval_count . _diffrn_standards_number 0 _diffrn_standards_decay_% . _diffrn_ambient_temperature 150 _diffrn_reflns_number 48778 _reflns_number_total 8185 _diffrn_reflns_av_R_equivalents 0.063 # Number of reflections with Friedels Law is 8185 # Number of reflections without Friedels Law is 16016 # Theoretical number of reflections is about 5615 _diffrn_reflns_theta_min 5.108 _diffrn_reflns_theta_max 27.144 _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 25.516 _diffrn_measured_fraction_theta_full 0.990 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _reflns_limit_h_min -13 _reflns_limit_h_max 13 _reflns_limit_k_min 0 _reflns_limit_k_max 24 _reflns_limit_l_min 0 _reflns_limit_l_max 23 _oxford_diffrn_Wilson_B_factor 2.57 _oxford_diffrn_Wilson_scale 7.29 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.27 _refine_diff_density_max 0.28 # The current dictionary definitions do not cover the # situation where the reflections used for refinement were # selected by a user-defined sigma threshold # The values actually used during refinement _oxford_reflns_threshold_expression_ref I>-3.0\s(I) _refine_ls_number_reflns 5552 _refine_ls_number_restraints 0 _refine_ls_number_parameters 388 _oxford_refine_ls_R_factor_ref 0.0590 _refine_ls_wR_factor_ref 0.0994 _refine_ls_goodness_of_fit_ref 1.0000 _refine_ls_shift/su_max 0.000376 # The values computed from all data _oxford_reflns_number_all 5552 _refine_ls_R_factor_all 0.0590 _refine_ls_wR_factor_all 0.0994 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 4301 _refine_ls_R_factor_gt 0.0407 _refine_ls_wR_factor_gt 0.0926 # choose from: rm (reference molecule of known chirality), # ad (anomolous dispersion - Flack), rmad (rm and ad), # syn (from synthesis), unk (unknown) or . (not applicable). _chemical_absolute_configuration . _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_hydrogen_treatment constr # none, undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method= Modified Sheldrick w=1/[\s^2^(F^2^) + ( 0.05P)^2^ + 1.32P] ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 ; # Insert your own references if required - in alphabetical order _publ_section_references ; Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M.C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435. Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. Nonius (1997-2001). COLLECT. Nonius BV, Delft, The Netherlands. Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, edited by C. W. Carter Jr & R. M. Sweet, pp. 307--326. New York: Academic Press. Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996). CAMERON, Chemical Crystallography Laboratory, Oxford, UK. ; # Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3 # Replace last . with number of unfound hydrogen atomsattached to an atom. # ..._refinement_flags_... # . no refinement constraints S special position constraint on site # G rigid group refinement of site R riding atom # D distance or angle restraint on site T thermal displacement constraints # U Uiso or Uij restraint (rigid bond) P partial occupancy constraint 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 _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _oxford_atom_site_special_shape _atom_site_attached_hydrogens F1 F 0.89827(8) 0.29337(4) 0.27894(4) 0.0306 1.0000 Uani . . . . . . . B2 B 0.86953(17) 0.34737(9) 0.33110(9) 0.0267 1.0000 Uani . . . . . . . C3 C 0.78320(14) 0.30289(8) 0.38671(8) 0.0253 1.0000 Uani . . . . . . . C4 C 0.82445(15) 0.28254(8) 0.45755(8) 0.0286 1.0000 Uani . . . . . . . C5 C 0.94455(16) 0.31017(9) 0.49915(9) 0.0374 1.0000 Uani . . . . . . . C6 C 0.75316(17) 0.23513(9) 0.49460(9) 0.0359 1.0000 Uani . . . . . . . C7 C 0.63744(18) 0.20724(9) 0.46620(9) 0.0408 1.0000 Uani . . . . . . . C8 C 0.59285(16) 0.22873(9) 0.39804(9) 0.0360 1.0000 Uani . . . . . . . C9 C 0.66226(15) 0.27487(8) 0.35855(8) 0.0282 1.0000 Uani . . . . . . . C10 C 0.59965(16) 0.29427(9) 0.28556(9) 0.0337 1.0000 Uani . . . . . . . C11 C 0.5619(2) 0.15695(12) 0.50835(12) 0.0705 1.0000 Uani . . . . . . . C12 C 0.79285(14) 0.41153(8) 0.28860(8) 0.0245 1.0000 Uani . . . . . . . C13 C 0.81269(14) 0.42708(8) 0.21607(8) 0.0266 1.0000 Uani . . . . . . . C14 C 0.75134(15) 0.48299(8) 0.18150(9) 0.0299 1.0000 Uani . . . . . . . C15 C 0.67123(15) 0.52741(8) 0.21599(9) 0.0313 1.0000 Uani . . . . . . . C16 C 0.65254(15) 0.51326(8) 0.28671(9) 0.0307 1.0000 Uani . . . . . . . C17 C 0.71009(14) 0.45706(8) 0.32304(8) 0.0263 1.0000 Uani . . . . . . . C18 C 0.67651(17) 0.44741(9) 0.39981(9) 0.0360 1.0000 Uani . . . . . . . C19 C 0.60934(17) 0.58881(9) 0.17786(10) 0.0457 1.0000 Uani . . . . . . . C20 C 0.90109(17) 0.38463(9) 0.17201(9) 0.0364 1.0000 Uani . . . . . . . C21 C 1.01075(15) 0.37757(8) 0.36304(8) 0.0277 1.0000 Uani . . . . . . . C22 C 1.02551(16) 0.44042(8) 0.39910(8) 0.0312 1.0000 Uani . . . . . . . C23 C 1.14473(17) 0.46370(9) 0.42880(9) 0.0390 1.0000 Uani . . . . . . . C24 C 1.25644(17) 0.42577(11) 0.42174(10) 0.0459 1.0000 Uani . . . . . . . C25 C 1.24672(17) 0.36495(11) 0.38415(10) 0.0459 1.0000 Uani . . . . . . . C26 C 1.12616(16) 0.34159(9) 0.35534(9) 0.0368 1.0000 Uani . . . . . . . N27 N 0.87515(12) 0.39907(6) 0.75861(6) 0.0257 1.0000 Uani . . . . . . . C28 C 0.90526(15) 0.36905(8) 0.83348(8) 0.0285 1.0000 Uani . . . . . . . C29 C 1.01326(16) 0.40435(9) 0.87876(9) 0.0347 1.0000 Uani . . . . . . . C30 C 1.0358(2) 0.37087(12) 0.95153(10) 0.0609 1.0000 Uani . . . . . . . C31 C 1.1404(2) 0.40624(13) 0.99950(11) 0.0678 1.0000 Uani . . . . . . . C32 C 0.99289(14) 0.39523(8) 0.71404(8) 0.0276 1.0000 Uani . . . . . . . C33 C 1.05258(16) 0.32497(8) 0.70658(9) 0.0344 1.0000 Uani . . . . . . . C34 C 1.16710(15) 0.32805(9) 0.66013(9) 0.0342 1.0000 Uani . . . . . . . C35 C 1.22690(19) 0.25795(10) 0.65038(12) 0.0540 1.0000 Uani . . . . . . . C36 C 0.84035(15) 0.47477(8) 0.76219(8) 0.0283 1.0000 Uani . . . . . . . C37 C 0.72452(16) 0.49237(8) 0.80388(9) 0.0337 1.0000 Uani . . . . . . . C38 C 0.70070(17) 0.56918(9) 0.80283(10) 0.0385 1.0000 Uani . . . . . . . C39 C 0.59106(16) 0.59049(9) 0.84724(10) 0.0395 1.0000 Uani . . . . . . . C40 C 0.76206(14) 0.35690(8) 0.72491(8) 0.0275 1.0000 Uani . . . . . . . C41 C 0.70688(15) 0.37878(9) 0.65116(9) 0.0333 1.0000 Uani . . . . . . . C42 C 0.58668(15) 0.33665(9) 0.62759(9) 0.0340 1.0000 Uani . . . . . . . C43 C 0.52339(17) 0.35995(10) 0.55548(9) 0.0444 1.0000 Uani . . . . . . . H51 H 0.9527 0.2897 0.5471 0.0539 1.0000 Uiso R . . . . . . H52 H 0.9402 0.3606 0.5047 0.0559 1.0000 Uiso R . . . . . . H53 H 1.0254 0.2998 0.4758 0.0551 1.0000 Uiso R . . . . . . H61 H 0.7849 0.2223 0.5428 0.0420 1.0000 Uiso R . . . . . . H81 H 0.5093 0.2123 0.3774 0.0423 1.0000 Uiso R . . . . . . H103 H 0.5305 0.2608 0.2707 0.0507 1.0000 Uiso R . . . . . . H102 H 0.5579 0.3401 0.2872 0.0502 1.0000 Uiso R . . . . . . H101 H 0.6642 0.2954 0.2487 0.0492 1.0000 Uiso R . . . . . . H111 H 0.4726 0.1589 0.4964 0.1072 1.0000 Uiso R . . . . . . H113 H 0.5811 0.1607 0.5586 0.1070 1.0000 Uiso R . . . . . . H112 H 0.5861 0.1107 0.4958 0.1088 1.0000 Uiso R . . . . . . H141 H 0.7649 0.4910 0.1318 0.0352 1.0000 Uiso R . . . . . . H161 H 0.5980 0.5428 0.3127 0.0375 1.0000 Uiso R . . . . . . H182 H 0.6558 0.4916 0.4203 0.0561 1.0000 Uiso R . . . . . . H181 H 0.7492 0.4263 0.4305 0.0529 1.0000 Uiso R . . . . . . H183 H 0.5984 0.4183 0.4016 0.0550 1.0000 Uiso R . . . . . . H191 H 0.5532 0.6154 0.2075 0.0705 1.0000 Uiso R . . . . . . H193 H 0.6687 0.6200 0.1593 0.0693 1.0000 Uiso R . . . . . . H192 H 0.5525 0.5740 0.1381 0.0705 1.0000 Uiso R . . . . . . H201 H 0.9180 0.4091 0.1277 0.0551 1.0000 Uiso R . . . . . . H203 H 0.9861 0.3747 0.1990 0.0544 1.0000 Uiso R . . . . . . H202 H 0.8589 0.3402 0.1593 0.0547 1.0000 Uiso R . . . . . . H221 H 0.9490 0.4689 0.4046 0.0372 1.0000 Uiso R . . . . . . H231 H 1.1508 0.5067 0.4549 0.0467 1.0000 Uiso R . . . . . . H241 H 1.3396 0.4421 0.4426 0.0543 1.0000 Uiso R . . . . . . H251 H 1.3213 0.3385 0.3779 0.0544 1.0000 Uiso R . . . . . . H261 H 1.1213 0.2988 0.3298 0.0436 1.0000 Uiso R . . . . . . H282 H 0.8236 0.3721 0.8573 0.0326 1.0000 Uiso R . . . . . . H281 H 0.9281 0.3212 0.8264 0.0347 1.0000 Uiso R . . . . . . H291 H 0.9905 0.4522 0.8861 0.0436 1.0000 Uiso R . . . . . . H292 H 1.0939 0.4022 0.8549 0.0422 1.0000 Uiso R . . . . . . H301 H 0.9545 0.3698 0.9744 0.0740 1.0000 Uiso R . . . . . . H302 H 1.0599 0.3234 0.9438 0.0738 1.0000 Uiso R . . . . . . H313 H 1.1514 0.3847 1.0452 0.1007 1.0000 Uiso R . . . . . . H312 H 1.1170 0.4549 1.0063 0.1011 1.0000 Uiso R . . . . . . H311 H 1.2228 0.4041 0.9771 0.1005 1.0000 Uiso R . . . . . . H322 H 1.0573 0.4267 0.7366 0.0320 1.0000 Uiso R . . . . . . H321 H 0.9628 0.4126 0.6662 0.0326 1.0000 Uiso R . . . . . . H331 H 1.0834 0.3076 0.7540 0.0428 1.0000 Uiso R . . . . . . H332 H 0.9867 0.2933 0.6849 0.0426 1.0000 Uiso R . . . . . . H342 H 1.2330 0.3589 0.6823 0.0418 1.0000 Uiso R . . . . . . H341 H 1.1375 0.3467 0.6132 0.0411 1.0000 Uiso R . . . . . . H351 H 1.3015 0.2605 0.6204 0.0812 1.0000 Uiso R . . . . . . H353 H 1.2582 0.2395 0.6969 0.0829 1.0000 Uiso R . . . . . . H352 H 1.1604 0.2267 0.6275 0.0822 1.0000 Uiso R . . . . . . H361 H 0.9188 0.4958 0.7843 0.0332 1.0000 Uiso R . . . . . . H362 H 0.8254 0.4904 0.7123 0.0325 1.0000 Uiso R . . . . . . H371 H 0.7393 0.4775 0.8535 0.0418 1.0000 Uiso R . . . . . . H372 H 0.6475 0.4692 0.7824 0.0422 1.0000 Uiso R . . . . . . H382 H 0.7815 0.5921 0.8216 0.0494 1.0000 Uiso R . . . . . . H381 H 0.6809 0.5835 0.7534 0.0492 1.0000 Uiso R . . . . . . H393 H 0.5827 0.6402 0.8463 0.0600 1.0000 Uiso R . . . . . . H392 H 0.6105 0.5753 0.8965 0.0601 1.0000 Uiso R . . . . . . H391 H 0.5096 0.5698 0.8274 0.0593 1.0000 Uiso R . . . . . . H401 H 0.6948 0.3609 0.7592 0.0316 1.0000 Uiso R . . . . . . H402 H 0.7933 0.3098 0.7242 0.0320 1.0000 Uiso R . . . . . . H412 H 0.6811 0.4270 0.6519 0.0400 1.0000 Uiso R . . . . . . H411 H 0.7720 0.3734 0.6157 0.0402 1.0000 Uiso R . . . . . . H422 H 0.5232 0.3415 0.6648 0.0408 1.0000 Uiso R . . . . . . H421 H 0.6117 0.2880 0.6261 0.0410 1.0000 Uiso R . . . . . . H431 H 0.4451 0.3336 0.5423 0.0658 1.0000 Uiso R . . . . . . H432 H 0.4988 0.4089 0.5582 0.0667 1.0000 Uiso R . . . . . . H433 H 0.5849 0.3538 0.5191 0.0652 1.0000 Uiso R . . . . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 F1 0.0378(5) 0.0240(5) 0.0308(5) -0.0045(4) 0.0077(4) 0.0016(4) B2 0.0320(10) 0.0228(10) 0.0257(10) -0.0037(8) 0.0048(8) 0.0021(8) C3 0.0287(8) 0.0191(8) 0.0283(9) -0.0040(7) 0.0035(7) 0.0027(7) C4 0.0336(9) 0.0251(9) 0.0276(9) -0.0011(7) 0.0049(7) 0.0037(7) C5 0.0419(10) 0.0418(11) 0.0276(9) 0.0065(8) -0.0017(8) -0.0028(8) C6 0.0474(10) 0.0328(10) 0.0281(9) 0.0042(8) 0.0073(8) -0.0003(8) C7 0.0524(11) 0.0347(11) 0.0367(10) 0.0012(8) 0.0132(9) -0.0109(9) C8 0.0356(9) 0.0322(10) 0.0408(11) -0.0054(8) 0.0076(8) -0.0103(8) C9 0.0317(9) 0.0225(9) 0.0308(9) -0.0039(7) 0.0057(7) 0.0012(7) C10 0.0324(9) 0.0305(10) 0.0375(10) -0.0021(8) -0.0022(8) -0.0038(7) C11 0.0867(16) 0.0741(17) 0.0518(13) 0.0116(12) 0.0129(12) -0.0423(13) C12 0.0252(8) 0.0219(8) 0.0262(8) -0.0026(7) 0.0006(7) -0.0049(6) C13 0.0266(8) 0.0263(9) 0.0265(9) -0.0011(7) 0.0000(7) -0.0079(7) C14 0.0290(9) 0.0334(10) 0.0268(9) 0.0063(7) -0.0015(7) -0.0091(7) C15 0.0253(8) 0.0270(9) 0.0407(10) 0.0068(8) -0.0028(7) -0.0050(7) C16 0.0272(8) 0.0248(9) 0.0402(10) -0.0016(8) 0.0026(7) -0.0006(7) C17 0.0281(8) 0.0217(9) 0.0289(8) -0.0010(7) 0.0010(7) -0.0021(7) C18 0.0441(10) 0.0321(10) 0.0326(9) -0.0030(8) 0.0080(8) 0.0081(8) C19 0.0390(10) 0.0406(11) 0.0572(12) 0.0198(9) 0.0016(9) 0.0035(8) C20 0.0438(10) 0.0376(11) 0.0289(9) 0.0017(8) 0.0102(8) -0.0009(8) C21 0.0319(9) 0.0279(9) 0.0237(8) 0.0050(7) 0.0041(7) 0.0001(7) C22 0.0348(9) 0.0299(10) 0.0285(9) 0.0037(7) 0.0011(7) -0.0045(7) C23 0.0456(11) 0.0380(11) 0.0322(10) 0.0040(8) -0.0050(8) -0.0121(9) C24 0.0369(10) 0.0604(14) 0.0389(11) 0.0070(10) -0.0065(8) -0.0122(9) C25 0.0307(10) 0.0623(14) 0.0445(11) 0.0058(10) 0.0019(8) 0.0049(9) C26 0.0339(10) 0.0408(11) 0.0361(10) 0.0011(8) 0.0043(8) 0.0021(8) N27 0.0285(7) 0.0216(7) 0.0270(7) 0.0003(6) 0.0029(6) -0.0035(5) C28 0.0320(8) 0.0271(9) 0.0265(9) 0.0029(7) 0.0027(7) -0.0028(7) C29 0.0355(9) 0.0359(10) 0.0322(9) 0.0028(8) 0.0006(8) -0.0075(8) C30 0.0659(13) 0.0725(16) 0.0414(12) 0.0168(11) -0.0148(10) -0.0300(12) C31 0.0677(14) 0.0938(18) 0.0387(12) 0.0143(12) -0.0163(10) -0.0295(13) C32 0.0264(8) 0.0270(9) 0.0298(9) 0.0007(7) 0.0046(7) -0.0025(7) C33 0.0393(10) 0.0266(9) 0.0380(10) 0.0016(8) 0.0077(8) 0.0009(8) C34 0.0315(9) 0.0306(10) 0.0408(10) -0.0045(8) 0.0045(8) -0.0039(7) C35 0.0503(12) 0.0409(12) 0.0735(14) -0.0053(10) 0.0232(10) 0.0075(9) C36 0.0323(9) 0.0220(9) 0.0309(9) -0.0009(7) 0.0043(7) -0.0018(7) C37 0.0340(9) 0.0316(10) 0.0363(10) -0.0018(8) 0.0069(7) -0.0009(7) C38 0.0411(10) 0.0309(10) 0.0448(11) -0.0039(8) 0.0121(8) -0.0005(8) C39 0.0363(10) 0.0367(11) 0.0461(11) -0.0078(9) 0.0075(8) 0.0003(8) C40 0.0274(8) 0.0244(9) 0.0307(9) -0.0013(7) 0.0026(7) -0.0041(7) C41 0.0356(9) 0.0323(10) 0.0320(9) 0.0018(8) 0.0021(7) -0.0022(8) C42 0.0325(9) 0.0395(10) 0.0298(9) 0.0005(8) 0.0016(7) -0.0035(8) C43 0.0441(10) 0.0518(12) 0.0360(10) 0.0018(9) -0.0056(8) -0.0005(9) _refine_ls_extinction_method None _oxford_refine_ls_scale 0.3840(4) 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 F1 . B2 . 1.4809(19) yes B2 . C3 . 1.664(2) yes B2 . C12 . 1.650(2) yes B2 . C21 . 1.639(2) yes C3 . C4 . 1.417(2) yes C3 . C9 . 1.424(2) yes C4 . C5 . 1.509(2) yes C4 . C6 . 1.397(2) yes C5 . H51 . 0.980 no C5 . H52 . 0.989 no C5 . H53 . 0.990 no C6 . C7 . 1.379(2) yes C6 . H61 . 0.968 no C7 . C8 . 1.387(2) yes C7 . C11 . 1.511(2) yes C8 . C9 . 1.396(2) yes C8 . H81 . 0.970 no C9 . C10 . 1.513(2) yes C10 . H103 . 0.990 no C10 . H102 . 0.993 no C10 . H101 . 0.995 no C11 . H111 . 0.931 no C11 . H113 . 0.948 no C11 . H112 . 0.968 no C12 . C13 . 1.420(2) yes C12 . C17 . 1.419(2) yes C13 . C14 . 1.394(2) yes C13 . C20 . 1.520(2) yes C14 . C15 . 1.389(2) yes C14 . H141 . 0.964 no C15 . C16 . 1.380(2) yes C15 . C19 . 1.509(2) yes C16 . C17 . 1.397(2) yes C16 . H161 . 0.963 no C17 . C18 . 1.515(2) yes C18 . H182 . 0.973 no C18 . H181 . 0.997 no C18 . H183 . 0.987 no C19 . H191 . 0.980 no C19 . H193 . 0.946 no C19 . H192 . 0.955 no C20 . H201 . 0.983 no C20 . H203 . 0.996 no C20 . H202 . 0.990 no C21 . C22 . 1.401(2) yes C21 . C26 . 1.397(2) yes C22 . C23 . 1.385(2) yes C22 . H221 . 0.975 no C23 . C24 . 1.383(3) yes C23 . H231 . 0.969 no C24 . C25 . 1.378(3) yes C24 . H241 . 0.967 no C25 . C26 . 1.392(2) yes C25 . H251 . 0.940 no C26 . H261 . 0.960 no N27 . C28 . 1.5277(19) yes N27 . C32 . 1.5259(19) yes N27 . C36 . 1.5214(19) yes N27 . C40 . 1.5223(18) yes C28 . C29 . 1.511(2) yes C28 . H282 . 0.984 no C28 . H281 . 0.974 no C29 . C30 . 1.512(2) yes C29 . H291 . 0.975 no C29 . H292 . 0.974 no C30 . C31 . 1.514(3) yes C30 . H301 . 0.969 no C30 . H302 . 0.972 no C31 . H313 . 0.951 no C31 . H312 . 0.989 no C31 . H311 . 0.976 no C32 . C33 . 1.512(2) yes C32 . H322 . 0.975 no C32 . H321 . 0.984 no C33 . C34 . 1.519(2) yes C33 . H331 . 0.979 no C33 . H332 . 0.981 no C34 . C35 . 1.516(2) yes C34 . H342 . 0.975 no C34 . H341 . 0.978 no C35 . H351 . 0.986 no C35 . H353 . 0.974 no C35 . H352 . 0.989 no C36 . C37 . 1.514(2) yes C36 . H361 . 0.970 no C36 . H362 . 0.982 no C37 . C38 . 1.517(2) yes C37 . H371 . 0.974 no C37 . H372 . 0.972 no C38 . C39 . 1.511(2) yes C38 . H382 . 0.985 no C38 . H381 . 0.973 no C39 . H393 . 0.973 no C39 . H392 . 0.974 no C39 . H391 . 0.978 no C40 . C41 . 1.513(2) yes C40 . H401 . 0.983 no C40 . H402 . 0.973 no C41 . C42 . 1.523(2) yes C41 . H412 . 0.977 no C41 . H411 . 0.985 no C42 . C43 . 1.522(2) yes C42 . H422 . 0.996 no C42 . H421 . 0.984 no C43 . H431 . 0.972 no C43 . H432 . 0.990 no C43 . H433 . 0.972 no 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 F1 . B2 . C3 . 100.66(12) yes F1 . B2 . C12 . 109.51(12) yes C3 . B2 . C12 . 115.93(12) yes F1 . B2 . C21 . 106.18(12) yes C3 . B2 . C21 . 117.49(13) yes C12 . B2 . C21 . 106.37(12) yes B2 . C3 . C4 . 126.49(13) yes B2 . C3 . C9 . 117.60(13) yes C4 . C3 . C9 . 115.43(14) yes C3 . C4 . C5 . 123.86(14) yes C3 . C4 . C6 . 121.20(15) yes C5 . C4 . C6 . 114.93(14) yes C4 . C5 . H51 . 109.6 no C4 . C5 . H52 . 111.5 no H51 . C5 . H52 . 108.0 no C4 . C5 . H53 . 112.5 no H51 . C5 . H53 . 107.8 no H52 . C5 . H53 . 107.2 no C4 . C6 . C7 . 122.79(16) yes C4 . C6 . H61 . 118.7 no C7 . C6 . H61 . 118.5 no C6 . C7 . C8 . 116.78(15) yes C6 . C7 . C11 . 121.29(17) yes C8 . C7 . C11 . 121.92(17) yes C7 . C8 . C9 . 122.33(15) yes C7 . C8 . H81 . 119.1 no C9 . C8 . H81 . 118.6 no C3 . C9 . C8 . 121.39(15) yes C3 . C9 . C10 . 122.56(14) yes C8 . C9 . C10 . 116.03(14) yes C9 . C10 . H103 . 109.7 no C9 . C10 . H102 . 110.7 no H103 . C10 . H102 . 107.3 no C9 . C10 . H101 . 111.7 no H103 . C10 . H101 . 108.9 no H102 . C10 . H101 . 108.4 no C7 . C11 . H111 . 112.7 no C7 . C11 . H113 . 113.0 no H111 . C11 . H113 . 111.2 no C7 . C11 . H112 . 109.0 no H111 . C11 . H112 . 104.4 no H113 . C11 . H112 . 105.9 no B2 . C12 . C13 . 121.55(13) yes B2 . C12 . C17 . 122.48(13) yes C13 . C12 . C17 . 115.85(14) yes C12 . C13 . C14 . 121.11(15) yes C12 . C13 . C20 . 122.57(14) yes C14 . C13 . C20 . 116.32(14) yes C13 . C14 . C15 . 122.44(15) yes C13 . C14 . H141 . 118.7 no C15 . C14 . H141 . 118.8 no C14 . C15 . C16 . 116.92(15) yes C14 . C15 . C19 . 121.29(15) yes C16 . C15 . C19 . 121.78(16) yes C15 . C16 . C17 . 122.55(15) yes C15 . C16 . H161 . 119.7 no C17 . C16 . H161 . 117.8 no C12 . C17 . C16 . 121.11(14) yes C12 . C17 . C18 . 122.82(14) yes C16 . C17 . C18 . 116.06(14) yes C17 . C18 . H182 . 109.7 no C17 . C18 . H181 . 112.4 no H182 . C18 . H181 . 108.5 no C17 . C18 . H183 . 110.5 no H182 . C18 . H183 . 106.9 no H181 . C18 . H183 . 108.7 no C15 . C19 . H191 . 113.4 no C15 . C19 . H193 . 114.9 no H191 . C19 . H193 . 107.1 no C15 . C19 . H192 . 109.9 no H191 . C19 . H192 . 104.3 no H193 . C19 . H192 . 106.4 no C13 . C20 . H201 . 110.2 no C13 . C20 . H203 . 111.8 no H201 . C20 . H203 . 108.4 no C13 . C20 . H202 . 109.6 no H201 . C20 . H202 . 109.0 no H203 . C20 . H202 . 107.7 no B2 . C21 . C22 . 123.36(14) yes B2 . C21 . C26 . 121.36(14) yes C22 . C21 . C26 . 115.28(15) yes C21 . C22 . C23 . 122.66(16) yes C21 . C22 . H221 . 119.3 no C23 . C22 . H221 . 118.0 no C22 . C23 . C24 . 120.35(17) yes C22 . C23 . H231 . 120.4 no C24 . C23 . H231 . 119.2 no C23 . C24 . C25 . 118.72(16) yes C23 . C24 . H241 . 120.2 no C25 . C24 . H241 . 121.0 no C24 . C25 . C26 . 120.44(17) yes C24 . C25 . H251 . 120.5 no C26 . C25 . H251 . 119.1 no C21 . C26 . C25 . 122.46(17) yes C21 . C26 . H261 . 118.4 no C25 . C26 . H261 . 119.2 no C28 . N27 . C32 . 111.62(11) yes C28 . N27 . C36 . 111.29(11) yes C32 . N27 . C36 . 105.76(11) yes C28 . N27 . C40 . 105.52(11) yes C32 . N27 . C40 . 111.25(11) yes C36 . N27 . C40 . 111.52(11) yes N27 . C28 . C29 . 115.36(12) yes N27 . C28 . H282 . 105.8 no C29 . C28 . H282 . 109.6 no N27 . C28 . H281 . 106.1 no C29 . C28 . H281 . 109.7 no H282 . C28 . H281 . 110.1 no C28 . C29 . C30 . 111.31(14) yes C28 . C29 . H291 . 109.9 no C30 . C29 . H291 . 108.0 no C28 . C29 . H292 . 109.9 no C30 . C29 . H292 . 108.5 no H291 . C29 . H292 . 109.2 no C29 . C30 . C31 . 112.94(16) yes C29 . C30 . H301 . 109.2 no C31 . C30 . H301 . 110.4 no C29 . C30 . H302 . 107.5 no C31 . C30 . H302 . 110.0 no H301 . C30 . H302 . 106.6 no C30 . C31 . H313 . 111.2 no C30 . C31 . H312 . 110.1 no H313 . C31 . H312 . 108.7 no C30 . C31 . H311 . 109.2 no H313 . C31 . H311 . 108.6 no H312 . C31 . H311 . 109.0 no N27 . C32 . C33 . 116.16(12) yes N27 . C32 . H322 . 106.0 no C33 . C32 . H322 . 110.0 no N27 . C32 . H321 . 105.8 no C33 . C32 . H321 . 109.2 no H322 . C32 . H321 . 109.5 no C32 . C33 . C34 . 110.87(13) yes C32 . C33 . H331 . 109.6 no C34 . C33 . H331 . 108.6 no C32 . C33 . H332 . 109.6 no C34 . C33 . H332 . 109.3 no H331 . C33 . H332 . 108.8 no C33 . C34 . C35 . 111.96(14) yes C33 . C34 . H342 . 109.1 no C35 . C34 . H342 . 109.3 no C33 . C34 . H341 . 109.0 no C35 . C34 . H341 . 109.2 no H342 . C34 . H341 . 108.2 no C34 . C35 . H351 . 111.3 no C34 . C35 . H353 . 109.6 no H351 . C35 . H353 . 108.0 no C34 . C35 . H352 . 109.4 no H351 . C35 . H352 . 109.3 no H353 . C35 . H352 . 109.3 no N27 . C36 . C37 . 116.12(12) yes N27 . C36 . H361 . 103.8 no C37 . C36 . H361 . 110.3 no N27 . C36 . H362 . 106.2 no C37 . C36 . H362 . 110.3 no H361 . C36 . H362 . 109.8 no C36 . C37 . C38 . 110.49(13) yes C36 . C37 . H371 . 110.7 no C38 . C37 . H371 . 108.6 no C36 . C37 . H372 . 109.4 no C38 . C37 . H372 . 109.1 no H371 . C37 . H372 . 108.6 no C37 . C38 . C39 . 113.03(14) yes C37 . C38 . H382 . 108.2 no C39 . C38 . H382 . 109.0 no C37 . C38 . H381 . 108.5 no C39 . C38 . H381 . 109.5 no H382 . C38 . H381 . 108.5 no C38 . C39 . H393 . 109.5 no C38 . C39 . H392 . 109.2 no H393 . C39 . H392 . 109.2 no C38 . C39 . H391 . 109.5 no H393 . C39 . H391 . 109.4 no H392 . C39 . H391 . 110.0 no N27 . C40 . C41 . 116.57(12) yes N27 . C40 . H401 . 104.0 no C41 . C40 . H401 . 109.8 no N27 . C40 . H402 . 105.8 no C41 . C40 . H402 . 110.8 no H401 . C40 . H402 . 109.5 no C40 . C41 . C42 . 110.62(13) yes C40 . C41 . H412 . 110.0 no C42 . C41 . H412 . 107.9 no C40 . C41 . H411 . 110.9 no C42 . C41 . H411 . 109.2 no H412 . C41 . H411 . 108.2 no C41 . C42 . C43 . 112.27(14) yes C41 . C42 . H422 . 108.1 no C43 . C42 . H422 . 109.4 no C41 . C42 . H421 . 108.6 no C43 . C42 . H421 . 111.0 no H422 . C42 . H421 . 107.4 no C42 . C43 . H431 . 111.0 no C42 . C43 . H432 . 109.7 no H431 . C43 . H432 . 108.2 no C42 . C43 . H433 . 109.0 no H431 . C43 . H433 . 109.2 no H432 . C43 . H433 . 109.8 no _chemical_name_common . #============================================================================== data_K_18-crown-6_1_CN _database_code_depnum_ccdc_archive 'CCDC 765940' #TrackingRef '- Combined structural data.cif' #============================================================================== _audit_creation_date 08-05-15 _audit_creation_method CRYSTALS_ver_12.85 _oxford_structure_analysis_title 5842 _chemical_name_systematic . _chemical_melting_point 'not measured' _cell_length_a 18.0486(2) _cell_length_b 15.72410(10) _cell_length_c 25.8240(2) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 7328.80(11) _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'P b c a ' _symmetry_space_group_name_Hall '-P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z -x+1/2,y+1/2,z x+1/2,-y+1/2,-z x,-y+1/2,z+1/2 -x,y+1/2,-z+1/2 -x+1/2,-y,z+1/2 x+1/2,y,-z+1/2 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 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4' B 0.0013 0.0007 2.0545 23.2185 1.3326 1.0210 1.0979 60.3498 0.7068 0.1403 -0.1932 'International Tables Vol C 4.2.6.8 and 6.1.1.4' K 0.2009 0.2494 8.2186 12.7949 7.4398 0.7748 1.0519 213.1870 0.8659 41.6841 1.4228 'International Tables Vol C 4.2.6.8 and 6.1.1.4' N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4' O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 8 # Given Formula = C37 H51 B1 K1 N1 O6 # Dc = 1.19 Fooo = 2816.00 Mu = 1.89 M = 655.72 # Found Formula = C37 H51 B1 K1 N1 O6 # Dc = 1.19 FOOO = 2816.00 Mu = 1.89 M = 655.72 _chemical_formula_sum 'C37 H51 B1 K1 N1 O6' _chemical_formula_moiety 'C37 H51 B1 K1 N1 O6' _chemical_compound_source . _chemical_formula_weight 655.72 _cell_measurement_reflns_used 9066 _cell_measurement_theta_min 5 _cell_measurement_theta_max 27 _cell_measurement_temperature 150 _exptl_crystal_description plate _exptl_crystal_colour clear_pale_colourless _exptl_crystal_size_min 0.11 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_max 0.20 _exptl_crystal_density_diffrn 1.189 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 2816 _exptl_absorpt_coefficient_mu 0.189 # Sheldrick geometric approximatio 0.97 0.98 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _exptl_absorpt_correction_T_min 0.84 _exptl_absorpt_correction_T_max 0.98 # For a Kappa CCD, set Tmin to 1.0 and # Tmax to the ratio of max:min frame scales in scale_all.log _diffrn_measurement_device 'Nonius KappaCCD' _diffrn_measurement_device_type Area _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method \w # If a reference occurs more than once, delete the author # and date from subsequent references. _computing_data_collection 'COLLECT (Nonius, 1997-2001).' _computing_cell_refinement 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_data_reduction 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _diffrn_standards_interval_time . _diffrn_standards_interval_count . _diffrn_standards_number 0 _diffrn_standards_decay_% . _diffrn_ambient_temperature 150 _diffrn_reflns_number 131038 _reflns_number_total 8314 _diffrn_reflns_av_R_equivalents 0.099 # Number of reflections with Friedels Law is 8314 # Number of reflections without Friedels Law is 16660 # Theoretical number of reflections is about 8372 _diffrn_reflns_theta_min 5.136 _diffrn_reflns_theta_max 27.452 _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 26.903 _diffrn_measured_fraction_theta_full 0.993 _diffrn_reflns_limit_h_min -23 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -33 _diffrn_reflns_limit_l_max 33 _reflns_limit_h_min -23 _reflns_limit_h_max 0 _reflns_limit_k_min 0 _reflns_limit_k_max 20 _reflns_limit_l_min 0 _reflns_limit_l_max 33 _oxford_diffrn_Wilson_B_factor 3.14 _oxford_diffrn_Wilson_scale 48.16 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.24 _refine_diff_density_max 0.23 # The current dictionary definitions do not cover the # situation where the reflections used for refinement were # selected by a user-defined sigma threshold # The values actually used during refinement _oxford_reflns_threshold_expression_ref I>2.0\s(I) _refine_ls_number_reflns 5181 _refine_ls_number_restraints 0 _refine_ls_number_parameters 415 _oxford_refine_ls_R_factor_ref 0.0459 _refine_ls_wR_factor_ref 0.0468 _refine_ls_goodness_of_fit_ref 1.0950 _refine_ls_shift/su_max 0.001085 # The values computed from all data _oxford_reflns_number_all 8314 _refine_ls_R_factor_all 0.0884 _refine_ls_wR_factor_all 0.0880 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 5181 _refine_ls_R_factor_gt 0.0459 _refine_ls_wR_factor_gt 0.0468 # choose from: rm (reference molecule of known chirality), # ad (anomolous dispersion - Flack), rmad (rm and ad), # syn (from synthesis), unk (unknown) or . (not applicable). _chemical_absolute_configuration . _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_hydrogen_treatment constr # none, undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ A~i~ are: 0.408 0.317 0.192 ; # Insert your own references if required - in alphabetical order _publ_section_references ; Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M.C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435. Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. Nonius (1997-2001). COLLECT. Nonius BV, Delft, The Netherlands. Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, edited by C. W. Carter Jr & R. M. Sweet, pp. 307--326. New York: Academic Press. Prince, E. Mathematical Techniques in Crystallography and Materials Science Springer-Verlag, New York, 1982. Watkin D.J. (1994). Acta Cryst, A50, 411-437. Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996). CAMERON, Chemical Crystallography Laboratory, Oxford, UK. ; # Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3 # Replace last . with number of unfound hydrogen atomsattached to an atom. # ..._refinement_flags_... # . no refinement constraints S special position constraint on site # G rigid group refinement of site R riding atom # D distance or angle restraint on site T thermal displacement constraints # U Uiso or Uij restraint (rigid bond) P partial occupancy constraint 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 _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _oxford_atom_site_special_shape _atom_site_attached_hydrogens K1 K 0.62337(2) 0.84795(3) 0.586810(17) 0.0375 1.0000 Uani . . . . . . . O2 O 0.68576(9) 0.68803(10) 0.61570(6) 0.0477 1.0000 Uani . . . . . . . C3 C 0.69081(16) 0.68042(17) 0.67074(10) 0.0584 1.0000 Uani . . . . . . . C4 C 0.73328(15) 0.75406(17) 0.69121(9) 0.0562 1.0000 Uani . . . . . . . O5 O 0.69015(9) 0.82859(10) 0.68310(6) 0.0498 1.0000 Uani . . . . . . . C6 C 0.72118(16) 0.90209(18) 0.70757(9) 0.0597 1.0000 Uani . . . . . . . C7 C 0.66989(17) 0.97503(18) 0.69916(9) 0.0606 1.0000 Uani . . . . . . . O8 O 0.66962(9) 0.99444(10) 0.64519(6) 0.0491 1.0000 Uani . . . . . . . C9 C 0.62059(16) 1.06266(16) 0.63327(10) 0.0584 1.0000 Uani . . . . . . . C10 C 0.63010(15) 1.08439(15) 0.57755(11) 0.0570 1.0000 Uani . . . . . . . O11 O 0.60524(8) 1.01473(10) 0.54692(6) 0.0445 1.0000 Uani . . . . . . . C12 C 0.61825(14) 1.02866(16) 0.49304(9) 0.0531 1.0000 Uani . . . . . . . C13 C 0.58586(14) 0.95723(19) 0.46281(9) 0.0573 1.0000 Uani . . . . . . . O14 O 0.61832(8) 0.87925(11) 0.47925(6) 0.0459 1.0000 Uani . . . . . . . C15 C 0.59140(15) 0.80815(19) 0.45052(9) 0.0599 1.0000 Uani . . . . . . . C16 C 0.63109(15) 0.72996(18) 0.46697(10) 0.0592 1.0000 Uani . . . . . . . O17 O 0.61450(9) 0.71199(11) 0.51984(6) 0.0490 1.0000 Uani . . . . . . . C18 C 0.64491(17) 0.63227(17) 0.53588(11) 0.0642 1.0000 Uani . . . . . . . C19 C 0.63919(16) 0.62486(16) 0.59342(11) 0.0617 1.0000 Uani . . . . . . . N20 N 0.47766(11) 0.81866(12) 0.61355(8) 0.0488 1.0000 Uani . . . . . . . C21 C 0.43276(11) 0.76622(13) 0.61333(8) 0.0355 1.0000 Uani . . . . . . . B22 B 0.37686(13) 0.68484(14) 0.61077(9) 0.0325 1.0000 Uani . . . . . . . C23 C 0.29471(10) 0.70669(12) 0.63614(7) 0.0287 1.0000 Uani . . . . . . . C24 C 0.25036(11) 0.64445(12) 0.66126(7) 0.0297 1.0000 Uani . . . . . . . C25 C 0.18199(11) 0.66525(13) 0.68287(7) 0.0338 1.0000 Uani . . . . . . . C26 C 0.15334(11) 0.74737(13) 0.68122(7) 0.0346 1.0000 Uani . . . . . . . C27 C 0.19430(11) 0.80767(13) 0.65453(7) 0.0334 1.0000 Uani . . . . . . . C28 C 0.26205(10) 0.78840(12) 0.63156(7) 0.0314 1.0000 Uani . . . . . . . C29 C 0.29648(12) 0.85784(13) 0.59895(8) 0.0405 1.0000 Uani . . . . . . . C30 C 0.07926(13) 0.76961(16) 0.70501(10) 0.0498 1.0000 Uani . . . . . . . C31 C 0.27332(12) 0.55194(12) 0.66471(8) 0.0374 1.0000 Uani . . . . . . . C32 C 0.36547(11) 0.66669(12) 0.54851(7) 0.0326 1.0000 Uani . . . . . . . C33 C 0.30232(11) 0.62428(13) 0.52976(8) 0.0359 1.0000 Uani . . . . . . . C34 C 0.29280(12) 0.60527(14) 0.47755(8) 0.0400 1.0000 Uani . . . . . . . C35 C 0.34553(13) 0.62972(14) 0.44163(8) 0.0437 1.0000 Uani . . . . . . . C36 C 0.40706(13) 0.67407(14) 0.45827(8) 0.0440 1.0000 Uani . . . . . . . C37 C 0.41647(12) 0.69157(13) 0.51074(8) 0.0389 1.0000 Uani . . . . . . . C38 C 0.42629(10) 0.61504(12) 0.64546(8) 0.0325 1.0000 Uani . . . . . . . C39 C 0.45816(11) 0.53865(13) 0.62645(8) 0.0362 1.0000 Uani . . . . . . . C40 C 0.44671(14) 0.50622(15) 0.57187(9) 0.0504 1.0000 Uani . . . . . . . C41 C 0.50177(12) 0.48711(13) 0.65852(9) 0.0405 1.0000 Uani . . . . . . . C42 C 0.51631(12) 0.50621(14) 0.70966(9) 0.0417 1.0000 Uani . . . . . . . C43 C 0.48475(11) 0.58059(14) 0.72896(8) 0.0401 1.0000 Uani . . . . . . . C44 C 0.44114(11) 0.63394(13) 0.69825(8) 0.0358 1.0000 Uani . . . . . . . C45 C 0.41009(13) 0.71175(15) 0.72513(9) 0.0457 1.0000 Uani . . . . . . . C46 C 0.56386(15) 0.44963(16) 0.74341(11) 0.0597 1.0000 Uani . . . . . . . H31 H 0.7151 0.6254 0.6793 0.0720 1.0000 Uiso R . . . . . . H32 H 0.6405 0.6798 0.6851 0.0717 1.0000 Uiso R . . . . . . H42 H 0.7413 0.7474 0.7299 0.0724 1.0000 Uiso R . . . . . . H41 H 0.7819 0.7605 0.6713 0.0730 1.0000 Uiso R . . . . . . H62 H 0.7267 0.8902 0.7460 0.0750 1.0000 Uiso R . . . . . . H61 H 0.7708 0.9147 0.6922 0.0754 1.0000 Uiso R . . . . . . H71 H 0.6861 1.0261 0.7195 0.0786 1.0000 Uiso R . . . . . . H72 H 0.6187 0.9584 0.7091 0.0786 1.0000 Uiso R . . . . . . H92 H 0.6325 1.1138 0.6547 0.0723 1.0000 Uiso R . . . . . . H91 H 0.5681 1.0433 0.6397 0.0726 1.0000 Uiso R . . . . . . H102 H 0.6837 1.0935 0.5706 0.0706 1.0000 Uiso R . . . . . . H101 H 0.6006 1.1361 0.5687 0.0707 1.0000 Uiso R . . . . . . H121 H 0.6725 1.0312 0.4866 0.0673 1.0000 Uiso R . . . . . . H122 H 0.5958 1.0847 0.4825 0.0675 1.0000 Uiso R . . . . . . H132 H 0.5965 0.9666 0.4250 0.0704 1.0000 Uiso R . . . . . . H131 H 0.5309 0.9550 0.4691 0.0706 1.0000 Uiso R . . . . . . H152 H 0.6004 0.8181 0.4123 0.0750 1.0000 Uiso R . . . . . . H151 H 0.5374 0.8027 0.4578 0.0754 1.0000 Uiso R . . . . . . H161 H 0.6853 0.7381 0.4640 0.0734 1.0000 Uiso R . . . . . . H162 H 0.6162 0.6806 0.4460 0.0740 1.0000 Uiso R . . . . . . H182 H 0.6971 0.6302 0.5246 0.0796 1.0000 Uiso R . . . . . . H181 H 0.6163 0.5848 0.5193 0.0795 1.0000 Uiso R . . . . . . H192 H 0.6573 0.5673 0.6045 0.0762 1.0000 Uiso R . . . . . . H191 H 0.5862 0.6344 0.6047 0.0762 1.0000 Uiso R . . . . . . H251 H 0.1530 0.6212 0.7002 0.0433 1.0000 Uiso R . . . . . . H271 H 0.1743 0.8644 0.6511 0.0436 1.0000 Uiso R . . . . . . H293 H 0.2589 0.9010 0.5893 0.0650 1.0000 Uiso R . . . . . . H292 H 0.3366 0.8865 0.6184 0.0652 1.0000 Uiso R . . . . . . H291 H 0.3178 0.8334 0.5670 0.0652 1.0000 Uiso R . . . . . . H303 H 0.0737 0.8311 0.7085 0.0812 1.0000 Uiso R . . . . . . H302 H 0.0745 0.7445 0.7391 0.0806 1.0000 Uiso R . . . . . . H301 H 0.0384 0.7491 0.6837 0.0808 1.0000 Uiso R . . . . . . H313 H 0.2304 0.5163 0.6743 0.0591 1.0000 Uiso R . . . . . . H312 H 0.3126 0.5435 0.6913 0.0590 1.0000 Uiso R . . . . . . H311 H 0.2924 0.5326 0.6308 0.0591 1.0000 Uiso R . . . . . . H331 H 0.2644 0.6078 0.5544 0.0467 1.0000 Uiso R . . . . . . H341 H 0.2488 0.5742 0.4660 0.0503 1.0000 Uiso R . . . . . . H351 H 0.3393 0.6166 0.4053 0.0557 1.0000 Uiso R . . . . . . H361 H 0.4439 0.6926 0.4344 0.0561 1.0000 Uiso R . . . . . . H371 H 0.4604 0.7223 0.5209 0.0478 1.0000 Uiso R . . . . . . H401 H 0.4719 0.4516 0.5687 0.0780 1.0000 Uiso R . . . . . . H403 H 0.4680 0.5461 0.5468 0.0784 1.0000 Uiso R . . . . . . H402 H 0.3929 0.4986 0.5654 0.0783 1.0000 Uiso R . . . . . . H411 H 0.5224 0.4354 0.6444 0.0506 1.0000 Uiso R . . . . . . H431 H 0.4933 0.5969 0.7651 0.0511 1.0000 Uiso R . . . . . . H452 H 0.4237 0.7090 0.7618 0.0697 1.0000 Uiso R . . . . . . H451 H 0.4280 0.7648 0.7093 0.0714 1.0000 Uiso R . . . . . . H453 H 0.3565 0.7095 0.7237 0.0708 1.0000 Uiso R . . . . . . H462 H 0.5418 0.4451 0.7777 0.0940 1.0000 Uiso R . . . . . . H461 H 0.6130 0.4745 0.7464 0.0940 1.0000 Uiso R . . . . . . H463 H 0.5673 0.3927 0.7276 0.0938 1.0000 Uiso R . . . . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 K1 0.0358(2) 0.0406(2) 0.0362(2) 0.00258(19) -0.00005(19) -0.0026(2) O2 0.0517(9) 0.0431(9) 0.0483(9) 0.0060(7) 0.0063(7) -0.0015(7) C3 0.0674(17) 0.0562(15) 0.0516(14) 0.0192(12) 0.0094(12) 0.0132(13) C4 0.0566(15) 0.0703(17) 0.0417(12) 0.0125(12) -0.0032(11) 0.0124(13) O5 0.0520(9) 0.0562(10) 0.0411(8) 0.0008(7) -0.0073(7) 0.0038(8) C6 0.0707(17) 0.0699(17) 0.0385(12) 0.0013(12) -0.0121(12) -0.0125(14) C7 0.0820(19) 0.0598(16) 0.0400(13) -0.0061(11) 0.0024(12) -0.0103(14) O8 0.0559(10) 0.0495(9) 0.0420(8) -0.0034(7) 0.0000(7) -0.0011(8) C9 0.0616(15) 0.0453(13) 0.0682(16) -0.0103(12) -0.0008(13) 0.0033(12) C10 0.0527(15) 0.0388(12) 0.0796(18) 0.0044(12) -0.0048(13) -0.0004(11) O11 0.0417(8) 0.0445(8) 0.0472(8) 0.0109(7) 0.0025(7) -0.0027(7) C12 0.0471(13) 0.0590(15) 0.0531(14) 0.0239(12) 0.0079(11) 0.0086(12) C13 0.0453(13) 0.0871(19) 0.0395(12) 0.0180(13) 0.0024(10) 0.0111(13) O14 0.0352(7) 0.0638(10) 0.0387(8) 0.0025(7) 0.0018(6) -0.0002(7) C15 0.0549(15) 0.088(2) 0.0365(12) -0.0054(12) 0.0023(11) -0.0202(14) C16 0.0588(15) 0.0703(17) 0.0484(13) -0.0180(12) 0.0133(12) -0.0114(13) O17 0.0438(9) 0.0565(10) 0.0466(9) -0.0082(7) 0.0060(7) -0.0034(7) C18 0.0675(17) 0.0498(15) 0.0752(18) -0.0185(13) -0.0019(14) 0.0001(13) C19 0.0652(17) 0.0386(12) 0.0814(19) 0.0024(13) 0.0019(14) -0.0038(12) N20 0.0428(11) 0.0454(11) 0.0580(12) -0.0064(9) 0.0085(9) -0.0097(9) C21 0.0321(10) 0.0351(11) 0.0394(11) -0.0023(9) 0.0062(8) 0.0002(9) B22 0.0317(11) 0.0280(10) 0.0377(11) -0.0036(9) 0.0038(9) -0.0028(9) C23 0.0280(9) 0.0299(9) 0.0283(9) -0.0028(7) 0.0015(7) -0.0022(7) C24 0.0318(9) 0.0299(10) 0.0275(8) 0.0010(7) -0.0014(8) -0.0014(8) C25 0.0314(10) 0.0371(11) 0.0328(10) 0.0019(8) 0.0027(8) -0.0041(8) C26 0.0305(10) 0.0397(11) 0.0336(10) -0.0006(8) 0.0043(8) 0.0002(9) C27 0.0328(10) 0.0322(10) 0.0353(10) -0.0021(8) 0.0024(8) 0.0026(8) C28 0.0320(10) 0.0311(10) 0.0312(9) -0.0008(8) 0.0026(8) -0.0014(8) C29 0.0420(11) 0.0295(10) 0.0499(12) 0.0061(9) 0.0101(9) 0.0024(9) C30 0.0381(12) 0.0560(14) 0.0553(14) 0.0028(11) 0.0136(10) 0.0032(11) C31 0.0388(11) 0.0305(10) 0.0429(11) 0.0025(8) 0.0019(9) -0.0047(9) C32 0.0331(10) 0.0285(10) 0.0363(10) -0.0005(8) 0.0046(8) 0.0038(8) C33 0.0309(10) 0.0387(10) 0.0380(11) -0.0004(9) 0.0010(8) 0.0033(8) C34 0.0369(11) 0.0433(12) 0.0400(11) -0.0022(9) -0.0039(9) 0.0046(9) C35 0.0497(13) 0.0463(12) 0.0351(11) -0.0014(9) 0.0026(10) 0.0063(10) C36 0.0502(13) 0.0437(12) 0.0381(11) -0.0005(9) 0.0137(10) 0.0004(10) C37 0.0380(11) 0.0355(11) 0.0433(12) -0.0026(9) 0.0079(9) -0.0014(9) C38 0.0266(9) 0.0319(10) 0.0391(10) -0.0030(8) 0.0030(8) -0.0016(8) C39 0.0334(10) 0.0311(10) 0.0442(11) -0.0013(8) 0.0036(9) 0.0000(8) C40 0.0590(15) 0.0390(12) 0.0530(14) -0.0133(10) -0.0048(11) 0.0148(11) C41 0.0343(10) 0.0321(11) 0.0551(13) -0.0001(10) 0.0033(9) 0.0023(9) C42 0.0330(11) 0.0365(11) 0.0556(13) 0.0066(10) -0.0056(10) -0.0010(9) C43 0.0337(10) 0.0447(12) 0.0420(11) 0.0011(10) -0.0042(9) -0.0052(9) C44 0.0300(10) 0.0370(11) 0.0403(11) -0.0045(8) 0.0010(8) -0.0018(8) C45 0.0462(12) 0.0506(13) 0.0404(11) -0.0131(10) -0.0075(10) 0.0087(11) C46 0.0549(15) 0.0526(15) 0.0716(17) 0.0073(13) -0.0160(13) 0.0082(12) _refine_ls_extinction_method None _oxford_refine_ls_scale 0.1477(2) 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 K1 . N20 . 2.7577(19) yes K1 . O14 . 2.8223(15) yes K1 . O11 . 2.8364(15) yes K1 . O8 . 2.8766(16) yes K1 . O5 . 2.7800(15) yes K1 . O2 . 2.8545(16) yes K1 . O17 . 2.7545(16) yes O2 . C3 . 1.429(3) yes O2 . C19 . 1.423(3) yes C3 . C4 . 1.486(4) yes C3 . H31 . 0.995 no C3 . H32 . 0.981 no C4 . O5 . 1.423(3) yes C4 . H42 . 1.014 no C4 . H41 . 1.021 no O5 . C6 . 1.431(3) yes C6 . C7 . 1.490(4) yes C6 . H62 . 1.015 no C6 . H61 . 1.000 no C7 . O8 . 1.427(3) yes C7 . H71 . 1.004 no C7 . H72 . 0.993 no O8 . C9 . 1.424(3) yes C9 . C10 . 1.489(4) yes C9 . H92 . 0.999 no C9 . H91 . 1.009 no C10 . O11 . 1.424(3) yes C10 . H102 . 0.995 no C10 . H101 . 0.998 no O11 . C12 . 1.428(3) yes C12 . C13 . 1.488(4) yes C12 . H121 . 0.994 no C12 . H122 . 1.007 no C13 . O14 . 1.424(3) yes C13 . H132 . 1.005 no C13 . H131 . 1.006 no O14 . C15 . 1.427(3) yes C15 . C16 . 1.485(4) yes C15 . H152 . 1.014 no C15 . H151 . 0.996 no C16 . O17 . 1.426(3) yes C16 . H161 . 0.989 no C16 . H162 . 0.985 no O17 . C18 . 1.430(3) yes C18 . C19 . 1.494(4) yes C18 . H182 . 0.987 no C18 . H181 . 1.002 no C19 . H192 . 1.004 no C19 . H191 . 1.011 no N20 . C21 . 1.156(3) yes C21 . B22 . 1.631(3) yes B22 . C23 . 1.657(3) yes B22 . C32 . 1.646(3) yes B22 . C38 . 1.674(3) yes C23 . C24 . 1.421(3) yes C23 . C28 . 1.418(3) yes C24 . C25 . 1.393(3) yes C24 . C31 . 1.515(3) yes C25 . C26 . 1.392(3) yes C25 . H251 . 0.977 no C26 . C27 . 1.386(3) yes C26 . C30 . 1.512(3) yes C27 . C28 . 1.392(3) yes C27 . H271 . 0.967 no C28 . C29 . 1.512(3) yes C29 . H293 . 0.992 no C29 . H292 . 0.990 no C29 . H291 . 0.987 no C30 . H303 . 0.976 no C30 . H302 . 0.968 no C30 . H301 . 0.976 no C31 . H313 . 0.988 no C31 . H312 . 0.995 no C31 . H311 . 0.989 no C32 . C33 . 1.406(3) yes C32 . C37 . 1.397(3) yes C33 . C34 . 1.392(3) yes C33 . H331 . 0.970 no C34 . C35 . 1.383(3) yes C34 . H341 . 0.979 no C35 . C36 . 1.380(3) yes C35 . H351 . 0.967 no C36 . C37 . 1.393(3) yes C36 . H361 . 0.951 no C37 . H371 . 0.964 no C38 . C39 . 1.419(3) yes C38 . C44 . 1.421(3) yes C39 . C40 . 1.513(3) yes C39 . C41 . 1.401(3) yes C40 . H401 . 0.975 no C40 . H403 . 0.980 no C40 . H402 . 0.992 no C41 . C42 . 1.379(3) yes C41 . H411 . 0.966 no C42 . C43 . 1.393(3) yes C42 . C46 . 1.513(3) yes C43 . C44 . 1.397(3) yes C43 . H431 . 0.980 no C44 . C45 . 1.514(3) yes C45 . H452 . 0.979 no C45 . H451 . 0.984 no C45 . H453 . 0.969 no C46 . H462 . 0.975 no C46 . H461 . 0.972 no C46 . H463 . 0.986 no 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 N20 . K1 . O14 . 104.17(5) yes N20 . K1 . O11 . 97.78(5) yes O14 . K1 . O11 . 58.51(5) yes N20 . K1 . O8 . 106.22(5) yes O14 . K1 . O8 . 112.68(5) yes O11 . K1 . O8 . 58.90(5) yes N20 . K1 . O5 . 99.86(6) yes O14 . K1 . O5 . 155.97(5) yes O11 . K1 . O5 . 118.43(5) yes O8 . K1 . O5 . 59.54(5) yes N20 . K1 . O2 . 99.42(5) yes O14 . K1 . O2 . 115.06(5) yes O11 . K1 . O2 . 162.73(5) yes O8 . K1 . O2 . 117.00(5) yes O5 . K1 . O2 . 59.92(5) yes N20 . K1 . O17 . 88.41(5) yes O14 . K1 . O17 . 61.02(5) yes O11 . K1 . O17 . 118.87(5) yes O8 . K1 . O17 . 165.32(5) yes O5 . K1 . O17 . 120.12(5) yes O2 . K1 . O17 . 60.21(5) yes C3 . O2 . C19 . 112.41(19) yes C3 . O2 . K1 . 111.03(14) yes C19 . O2 . K1 . 106.04(14) yes O2 . C3 . C4 . 108.8(2) yes O2 . C3 . H31 . 108.8 no C4 . C3 . H31 . 111.8 no O2 . C3 . H32 . 108.6 no C4 . C3 . H32 . 110.5 no H31 . C3 . H32 . 108.4 no C3 . C4 . O5 . 107.9(2) yes C3 . C4 . H42 . 110.1 no O5 . C4 . H42 . 107.9 no C3 . C4 . H41 . 110.0 no O5 . C4 . H41 . 108.3 no H42 . C4 . H41 . 112.5 no C4 . O5 . C6 . 112.71(19) yes C4 . O5 . K1 . 117.34(13) yes C6 . O5 . K1 . 118.43(13) yes O5 . C6 . C7 . 108.3(2) yes O5 . C6 . H62 . 108.8 no C7 . C6 . H62 . 110.2 no O5 . C6 . H61 . 109.6 no C7 . C6 . H61 . 110.3 no H62 . C6 . H61 . 109.7 no C6 . C7 . O8 . 108.0(2) yes C6 . C7 . H71 . 111.0 no O8 . C7 . H71 . 110.0 no C6 . C7 . H72 . 109.7 no O8 . C7 . H72 . 107.7 no H71 . C7 . H72 . 110.3 no C7 . O8 . C9 . 111.97(19) yes C7 . O8 . K1 . 109.98(14) yes C9 . O8 . K1 . 108.03(13) yes O8 . C9 . C10 . 108.1(2) yes O8 . C9 . H92 . 110.7 no C10 . C9 . H92 . 109.0 no O8 . C9 . H91 . 108.7 no C10 . C9 . H91 . 109.7 no H92 . C9 . H91 . 110.7 no C9 . C10 . O11 . 108.9(2) yes C9 . C10 . H102 . 108.7 no O11 . C10 . H102 . 108.5 no C9 . C10 . H101 . 110.3 no O11 . C10 . H101 . 109.4 no H102 . C10 . H101 . 111.1 no C10 . O11 . C12 . 111.81(18) yes C10 . O11 . K1 . 118.24(13) yes C12 . O11 . K1 . 118.48(13) yes O11 . C12 . C13 . 109.32(19) yes O11 . C12 . H121 . 109.3 no C13 . C12 . H121 . 109.3 no O11 . C12 . H122 . 109.4 no C13 . C12 . H122 . 111.1 no H121 . C12 . H122 . 108.4 no C12 . C13 . O14 . 109.39(19) yes C12 . C13 . H132 . 108.9 no O14 . C13 . H132 . 109.7 no C12 . C13 . H131 . 109.2 no O14 . C13 . H131 . 109.2 no H132 . C13 . H131 . 110.4 no C13 . O14 . C15 . 112.31(19) yes C13 . O14 . K1 . 117.19(13) yes C15 . O14 . K1 . 112.71(14) yes O14 . C15 . C16 . 109.6(2) yes O14 . C15 . H152 . 109.4 no C16 . C15 . H152 . 109.2 no O14 . C15 . H151 . 107.6 no C16 . C15 . H151 . 110.3 no H152 . C15 . H151 . 110.8 no C15 . C16 . O17 . 109.7(2) yes C15 . C16 . H161 . 110.3 no O17 . C16 . H161 . 107.9 no C15 . C16 . H162 . 111.3 no O17 . C16 . H162 . 108.3 no H161 . C16 . H162 . 109.3 no C16 . O17 . C18 . 111.7(2) yes C16 . O17 . K1 . 115.79(14) yes C18 . O17 . K1 . 118.45(14) yes O17 . C18 . C19 . 109.3(2) yes O17 . C18 . H182 . 108.1 no C19 . C18 . H182 . 110.9 no O17 . C18 . H181 . 109.3 no C19 . C18 . H181 . 109.3 no H182 . C18 . H181 . 110.0 no C18 . C19 . O2 . 107.9(2) yes C18 . C19 . H192 . 109.4 no O2 . C19 . H192 . 108.7 no C18 . C19 . H191 . 109.9 no O2 . C19 . H191 . 109.9 no H192 . C19 . H191 . 111.1 no C21 . N20 . K1 . 141.85(16) yes N20 . C21 . B22 . 173.4(2) yes C21 . B22 . C23 . 112.01(16) yes C21 . B22 . C32 . 104.65(16) yes C23 . B22 . C32 . 108.08(16) yes C21 . B22 . C38 . 99.39(16) yes C23 . B22 . C38 . 113.65(16) yes C32 . B22 . C38 . 118.41(16) yes B22 . C23 . C24 . 122.80(16) yes B22 . C23 . C28 . 121.79(16) yes C24 . C23 . C28 . 115.32(16) yes C23 . C24 . C25 . 121.34(17) yes C23 . C24 . C31 . 122.27(17) yes C25 . C24 . C31 . 116.37(17) yes C24 . C25 . C26 . 122.32(18) yes C24 . C25 . H251 . 119.4 no C26 . C25 . H251 . 118.2 no C25 . C26 . C27 . 116.85(18) yes C25 . C26 . C30 . 122.05(18) yes C27 . C26 . C30 . 121.03(19) yes C26 . C27 . C28 . 122.11(18) yes C26 . C27 . H271 . 118.5 no C28 . C27 . H271 . 119.4 no C23 . C28 . C27 . 121.77(17) yes C23 . C28 . C29 . 121.98(17) yes C27 . C28 . C29 . 116.16(17) yes C28 . C29 . H293 . 110.7 no C28 . C29 . H292 . 110.2 no H293 . C29 . H292 . 108.5 no C28 . C29 . H291 . 110.1 no H293 . C29 . H291 . 108.8 no H292 . C29 . H291 . 108.5 no C26 . C30 . H303 . 110.9 no C26 . C30 . H302 . 110.7 no H303 . C30 . H302 . 108.0 no C26 . C30 . H301 . 111.2 no H303 . C30 . H301 . 107.6 no H302 . C30 . H301 . 108.1 no C24 . C31 . H313 . 110.2 no C24 . C31 . H312 . 111.3 no H313 . C31 . H312 . 108.1 no C24 . C31 . H311 . 109.8 no H313 . C31 . H311 . 108.6 no H312 . C31 . H311 . 108.8 no B22 . C32 . C33 . 121.32(17) yes B22 . C32 . C37 . 123.45(18) yes C33 . C32 . C37 . 115.24(18) yes C32 . C33 . C34 . 122.37(19) yes C32 . C33 . H331 . 118.2 no C34 . C33 . H331 . 119.4 no C33 . C34 . C35 . 120.3(2) yes C33 . C34 . H341 . 120.2 no C35 . C34 . H341 . 119.5 no C34 . C35 . C36 . 119.0(2) yes C34 . C35 . H351 . 120.8 no C36 . C35 . H351 . 120.2 no C35 . C36 . C37 . 120.1(2) yes C35 . C36 . H361 . 121.0 no C37 . C36 . H361 . 119.0 no C32 . C37 . C36 . 122.9(2) yes C32 . C37 . H371 . 119.4 no C36 . C37 . H371 . 117.7 no B22 . C38 . C39 . 125.85(17) yes B22 . C38 . C44 . 118.48(16) yes C39 . C38 . C44 . 115.62(18) yes C38 . C39 . C40 . 123.51(19) yes C38 . C39 . C41 . 120.86(19) yes C40 . C39 . C41 . 115.62(18) yes C39 . C40 . H401 . 108.2 no C39 . C40 . H403 . 110.3 no H401 . C40 . H403 . 108.9 no C39 . C40 . H402 . 109.3 no H401 . C40 . H402 . 109.6 no H403 . C40 . H402 . 110.5 no C39 . C41 . C42 . 123.2(2) yes C39 . C41 . H411 . 118.7 no C42 . C41 . H411 . 118.1 no C41 . C42 . C43 . 116.58(19) yes C41 . C42 . C46 . 122.1(2) yes C43 . C42 . C46 . 121.3(2) yes C42 . C43 . C44 . 122.1(2) yes C42 . C43 . H431 . 119.7 no C44 . C43 . H431 . 118.2 no C38 . C44 . C43 . 121.68(19) yes C38 . C44 . C45 . 122.61(18) yes C43 . C44 . C45 . 115.70(18) yes C44 . C45 . H452 . 108.3 no C44 . C45 . H451 . 112.0 no H452 . C45 . H451 . 110.9 no C44 . C45 . H453 . 108.8 no H452 . C45 . H453 . 106.5 no H451 . C45 . H453 . 110.1 no C42 . C46 . H462 . 109.6 no C42 . C46 . H461 . 109.1 no H462 . C46 . H461 . 109.3 no C42 . C46 . H463 . 109.3 no H462 . C46 . H463 . 109.7 no H461 . C46 . H463 . 109.9 no loop_ _geom_hbond_atom_site_label_D _geom_hbond_site_symmetry_D _geom_hbond_atom_site_label_H _geom_hbond_site_symmetry_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_angle_DHA _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_publ_flag C13 . H131 . O11 2_676 157 1.01 2.54 3.486(3) yes _chemical_name_common . #============================================================================== data_K_18-crown-6_2_2_CN_2_2MeCN _database_code_depnum_ccdc_archive 'CCDC 765941' #TrackingRef '- Combined structural data.cif' #============================================================================== _audit_creation_date 10-01-14 _audit_creation_method CRYSTALS_ver_12.86 _oxford_structure_analysis_title sa0701 _chemical_name_systematic . _chemical_melting_point 'not measured' _cell_length_a 12.5667(2) _cell_length_b 13.3168(3) _cell_length_c 13.9064(3) _cell_angle_alpha 102.2770(10) _cell_angle_beta 110.0420(10) _cell_angle_gamma 109.9540(10) _cell_volume 1906.52(7) _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P -1 ' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-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 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4' N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4' O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4' K 0.2009 0.2494 8.2186 12.7949 7.4398 0.7748 1.0519 213.1870 0.8659 41.6841 1.4228 'International Tables Vol C 4.2.6.8 and 6.1.1.4' B 0.0013 0.0007 2.0545 23.2185 1.3326 1.0210 1.0979 60.3498 0.7068 0.1403 -0.1932 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 1 # Given Formula = C80 H106 B2 K2 N4 O12 # Dc = 1.23 Fooo = 758.00 Mu = 1.87 M = 707.78 # Found Formula = C80 H106 B2 K2 N4 O12 # Dc = 1.23 FOOO = 758.00 Mu = 1.87 M = 707.78 _chemical_formula_sum 'C80 H106 B2 K2 N4 O12' _chemical_formula_moiety 'C76 H100 B2 K2 N2 O12, 2(C2 H3 N)' _chemical_compound_source . _chemical_formula_weight 1415.56 _cell_measurement_reflns_used 5459 _cell_measurement_theta_min 4 _cell_measurement_theta_max 26 _cell_measurement_temperature 293 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_min 0.08 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_max 0.25 _exptl_crystal_density_diffrn 1.233 _exptl_crystal_density_meas . _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 758 _exptl_absorpt_coefficient_mu 0.187 # Sheldrick geometric approximatio 0.97 0.99 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _exptl_absorpt_correction_T_min 0.95 _exptl_absorpt_correction_T_max 0.99 # For a Kappa CCD, set Tmin to 1.0 and # Tmax to the ratio of max:min frame scales in scale_all.log _diffrn_measurement_device 'Nonius KappaCCD' _diffrn_measurement_device_type Area _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method \w/2\q # If a reference occurs more than once, delete the author # and date from subsequent references. _computing_data_collection 'COLLECT (Nonius, 1997-2001).' _computing_cell_refinement 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_data_reduction 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS 86 (Sheldrick, 1986)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _diffrn_standards_interval_time . _diffrn_standards_interval_count . _diffrn_standards_number 0 _diffrn_standards_decay_% . _diffrn_ambient_temperature 293 _diffrn_reflns_number 28042 _reflns_number_total 7775 _diffrn_reflns_av_R_equivalents 0.123 # Number of reflections with Friedels Law is 7775 # Number of reflections without Friedels Law is 8719 # Theoretical number of reflections is about 8892 _diffrn_reflns_theta_min 2.846 _diffrn_reflns_theta_max 27.649 _diffrn_measured_fraction_theta_max 0.980 _diffrn_reflns_theta_full 27.096 _diffrn_measured_fraction_theta_full 0.996 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 18 _reflns_limit_h_min -16 _reflns_limit_h_max 15 _reflns_limit_k_min -17 _reflns_limit_k_max 16 _reflns_limit_l_min 0 _reflns_limit_l_max 18 _oxford_diffrn_Wilson_B_factor 0.00 _oxford_diffrn_Wilson_scale 0.00 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.64 _refine_diff_density_max 0.66 # The current dictionary definitions do not cover the # situation where the reflections used for refinement were # selected by a user-defined sigma threshold # The values actually used during refinement _oxford_reflns_threshold_expression_ref I>-3.0\s(I) _refine_ls_number_reflns 8697 _refine_ls_number_restraints 0 _refine_ls_number_parameters 451 _oxford_refine_ls_R_factor_ref 0.0980 _refine_ls_wR_factor_ref 0.1496 _refine_ls_goodness_of_fit_ref 0.9399 _refine_ls_shift/su_max 0.000176 # The values computed from all data _oxford_reflns_number_all 8697 _refine_ls_R_factor_all 0.0980 _refine_ls_wR_factor_all 0.1496 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 5882 _refine_ls_R_factor_gt 0.0604 _refine_ls_wR_factor_gt 0.1342 # choose from: rm (reference molecule of known chirality), # ad (anomolous dispersion - Flack), rmad (rm and ad), # syn (from synthesis), unk (unknown) or . (not applicable). _chemical_absolute_configuration . _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_hydrogen_treatment constr # none, undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method= Modified Sheldrick w=1/[\s^2^(F^2^) + ( 0.07P)^2^ + 1.26P] ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 ; # Insert your own references if required - in alphabetical order _publ_section_references ; Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. Nonius (1997-2001). COLLECT. Nonius BV, Delft, The Netherlands. Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, edited by C. W. Carter Jr & R. M. Sweet, pp. 307--326. New York: Academic Press. Sheldrick, G. M. (2008). Acta Cryst A64, 112-122. Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996). CAMERON, Chemical Crystallography Laboratory, Oxford, UK. ; # Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3 # Replace last . with number of unfound hydrogen atomsattached to an atom. # ..._refinement_flags_... # . no refinement constraints S special position constraint on site # G rigid group refinement of site R riding atom # D distance or angle restraint on site T thermal displacement constraints # U Uiso or Uij restraint (rigid bond) P partial occupancy constraint 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 _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _oxford_atom_site_special_shape _atom_site_attached_hydrogens K1 K 0.52770(5) 0.38468(4) 0.34633(4) 0.0268 1.0000 Uani . . . . . . . O2 O 0.61549(16) 0.42917(15) 0.58160(13) 0.0314 1.0000 Uani . . . . . . . C3 C 0.5787(2) 0.3226(2) 0.59762(19) 0.0309 1.0000 Uani . . . . . . . C4 C 0.4387(2) 0.2497(2) 0.52983(19) 0.0299 1.0000 Uani . . . . . . . O5 O 0.40806(15) 0.22969(14) 0.41686(13) 0.0278 1.0000 Uani . . . . . . . C6 C 0.2863(2) 0.1358(2) 0.3429(2) 0.0278 1.0000 Uani . . . . . . . C7 C 0.2688(2) 0.1167(2) 0.2274(2) 0.0286 1.0000 Uani . . . . . . . O8 O 0.27121(15) 0.21595(14) 0.20373(12) 0.0271 1.0000 Uani . . . . . . . C9 C 0.2478(2) 0.2001(2) 0.0922(2) 0.0340 1.0000 Uani . . . . . . . C10 C 0.2728(2) 0.3129(2) 0.0786(2) 0.0344 1.0000 Uani . . . . . . . O11 O 0.40486(16) 0.38695(15) 0.14290(14) 0.0338 1.0000 Uani . . . . . . . C12 C 0.4473(3) 0.4934(2) 0.1297(2) 0.0379 1.0000 Uani . . . . . . . C13 C 0.5893(3) 0.5470(2) 0.1798(2) 0.0401 1.0000 Uani . . . . . . . O14 O 0.63924(16) 0.57282(15) 0.29536(13) 0.0312 1.0000 Uani . . . . . . . C15 C 0.7723(2) 0.6079(2) 0.3466(2) 0.0346 1.0000 Uani . . . . . . . C16 C 0.8213(2) 0.6531(2) 0.4689(2) 0.0328 1.0000 Uani . . . . . . . O17 O 0.76409(15) 0.56208(14) 0.50033(13) 0.0303 1.0000 Uani . . . . . . . C18 C 0.7880(3) 0.6013(2) 0.6121(2) 0.0349 1.0000 Uani . . . . . . . C19 C 0.7486(2) 0.5001(2) 0.6449(2) 0.0358 1.0000 Uani . . . . . . . N20 N 0.58886(19) 0.21967(18) 0.24232(16) 0.0282 1.0000 Uani . . . . . . . C21 C 0.6301(2) 0.1557(2) 0.25614(17) 0.0209 1.0000 Uani . . . . . . . B22 B 0.6860(2) 0.0627(2) 0.26918(19) 0.0187 1.0000 Uani . . . . . . . C23 C 0.78952(19) 0.09887(19) 0.39898(17) 0.0200 1.0000 Uani . . . . . . . C24 C 0.81686(19) 0.0136(2) 0.43219(18) 0.0213 1.0000 Uani . . . . . . . C25 C 0.8842(2) 0.0328(2) 0.54311(19) 0.0248 1.0000 Uani . . . . . . . C26 C 0.9261(2) 0.1358(2) 0.62703(18) 0.0255 1.0000 Uani . . . . . . . C27 C 0.9102(2) 0.2236(2) 0.59545(18) 0.0250 1.0000 Uani . . . . . . . C28 C 0.8472(2) 0.2082(2) 0.48471(18) 0.0229 1.0000 Uani . . . . . . . C29 C 0.8484(2) 0.3154(2) 0.4633(2) 0.0326 1.0000 Uani . . . . . . . C30 C 0.9913(2) 0.1528(2) 0.7476(2) 0.0364 1.0000 Uani . . . . . . . C31 C 0.7779(2) -0.1024(2) 0.34978(19) 0.0262 1.0000 Uani . . . . . . . C32 C 0.5549(2) -0.05773(19) 0.23222(17) 0.0199 1.0000 Uani . . . . . . . C33 C 0.4843(2) -0.0517(2) 0.29339(18) 0.0223 1.0000 Uani . . . . . . . C34 C 0.3661(2) -0.1424(2) 0.26035(19) 0.0265 1.0000 Uani . . . . . . . C35 C 0.3127(2) -0.2436(2) 0.17049(19) 0.0264 1.0000 Uani . . . . . . . C36 C 0.3854(2) -0.2528(2) 0.11688(19) 0.0251 1.0000 Uani . . . . . . . C37 C 0.5034(2) -0.1636(2) 0.14515(18) 0.0220 1.0000 Uani . . . . . . . C38 C 0.5680(2) -0.1932(2) 0.07737(19) 0.0258 1.0000 Uani . . . . . . . C39 C 0.1829(2) -0.3385(2) 0.1343(2) 0.0405 1.0000 Uani . . . . . . . C40 C 0.5332(2) 0.0489(2) 0.39737(19) 0.0274 1.0000 Uani . . . . . . . C41 C 0.75604(19) 0.07221(18) 0.18765(17) 0.0186 1.0000 Uani . . . . . . . C42 C 0.8862(2) 0.10626(19) 0.22740(18) 0.0220 1.0000 Uani . . . . . . . C43 C 0.9497(2) 0.1273(2) 0.16379(19) 0.0259 1.0000 Uani . . . . . . . C44 C 0.8849(2) 0.1175(2) 0.05707(19) 0.0255 1.0000 Uani . . . . . . . C45 C 0.7551(2) 0.08342(19) 0.01273(18) 0.0229 1.0000 Uani . . . . . . . C46 C 0.6914(2) 0.06003(19) 0.07645(17) 0.0201 1.0000 Uani . . . . . . . C47 C 0.5564(2) 0.01980(19) 0.02406(17) 0.0205 1.0000 Uani . . . . . . . N48 N 0.1473(3) 0.4600(2) 0.8820(2) 0.0557 1.0000 Uani . . . . . . . C49 C 0.1457(3) 0.5331(2) 0.8525(2) 0.0384 1.0000 Uani . . . . . . . C50 C 0.1490(4) 0.6269(3) 0.8161(3) 0.0637 1.0000 Uani . . . . . . . H31 H 0.5998 0.3388 0.6758 0.0347 1.0000 Uiso R . . . . . . H32 H 0.6244 0.2813 0.5746 0.0352 1.0000 Uiso R . . . . . . H42 H 0.3920 0.2877 0.5527 0.0371 1.0000 Uiso R . . . . . . H41 H 0.4152 0.1751 0.5385 0.0372 1.0000 Uiso R . . . . . . H62 H 0.2808 0.0653 0.3574 0.0323 1.0000 Uiso R . . . . . . H61 H 0.2211 0.1545 0.3516 0.0312 1.0000 Uiso R . . . . . . H71 H 0.3357 0.0997 0.2181 0.0327 1.0000 Uiso R . . . . . . H72 H 0.1858 0.0498 0.1763 0.0310 1.0000 Uiso R . . . . . . H92 H 0.3053 0.1715 0.0764 0.0368 1.0000 Uiso R . . . . . . H91 H 0.1596 0.1437 0.0412 0.0362 1.0000 Uiso R . . . . . . H102 H 0.2477 0.3027 0.0007 0.0368 1.0000 Uiso R . . . . . . H101 H 0.2239 0.3450 0.1035 0.0381 1.0000 Uiso R . . . . . . H121 H 0.4182 0.5444 0.1656 0.0474 1.0000 Uiso R . . . . . . H122 H 0.4116 0.4800 0.0506 0.0472 1.0000 Uiso R . . . . . . H132 H 0.6206 0.6185 0.1667 0.0489 1.0000 Uiso R . . . . . . H131 H 0.6159 0.4927 0.1477 0.0481 1.0000 Uiso R . . . . . . H151 H 0.8179 0.6689 0.3263 0.0412 1.0000 Uiso R . . . . . . H152 H 0.7888 0.5416 0.3242 0.0414 1.0000 Uiso R . . . . . . H162 H 0.9131 0.6829 0.5059 0.0384 1.0000 Uiso R . . . . . . H161 H 0.8016 0.7178 0.4916 0.0379 1.0000 Uiso R . . . . . . H182 H 0.8778 0.6523 0.6595 0.0374 1.0000 Uiso R . . . . . . H181 H 0.7377 0.6434 0.6193 0.0375 1.0000 Uiso R . . . . . . H191 H 0.7693 0.5295 0.7235 0.0369 1.0000 Uiso R . . . . . . H192 H 0.7929 0.4552 0.6314 0.0354 1.0000 Uiso R . . . . . . H251 H 0.9004 -0.0267 0.5611 0.0287 1.0000 Uiso R . . . . . . H271 H 0.9430 0.2978 0.6496 0.0284 1.0000 Uiso R . . . . . . H291 H 0.9219 0.3836 0.5245 0.0420 1.0000 Uiso R . . . . . . H293 H 0.8568 0.3141 0.3952 0.0418 1.0000 Uiso R . . . . . . H292 H 0.7710 0.3222 0.4577 0.0427 1.0000 Uiso R . . . . . . H301 H 1.0611 0.2292 0.7876 0.0510 1.0000 Uiso R . . . . . . H303 H 1.0231 0.0970 0.7547 0.0511 1.0000 Uiso R . . . . . . H302 H 0.9312 0.1444 0.7776 0.0505 1.0000 Uiso R . . . . . . H311 H 0.8324 -0.1355 0.3806 0.0409 1.0000 Uiso R . . . . . . H313 H 0.7826 -0.0946 0.2832 0.0409 1.0000 Uiso R . . . . . . H312 H 0.6925 -0.1560 0.3287 0.0409 1.0000 Uiso R . . . . . . H341 H 0.3200 -0.1343 0.3017 0.0331 1.0000 Uiso R . . . . . . H361 H 0.3524 -0.3234 0.0570 0.0283 1.0000 Uiso R . . . . . . H382 H 0.5577 -0.2711 0.0669 0.0392 1.0000 Uiso R . . . . . . H381 H 0.6586 -0.1391 0.1115 0.0389 1.0000 Uiso R . . . . . . H383 H 0.5309 -0.1908 0.0063 0.0395 1.0000 Uiso R . . . . . . H393 H 0.1807 -0.4124 0.1052 0.0540 1.0000 Uiso R . . . . . . H392 H 0.1643 -0.3345 0.1965 0.0545 1.0000 Uiso R . . . . . . H391 H 0.1189 -0.3290 0.0790 0.0543 1.0000 Uiso R . . . . . . H403 H 0.4717 0.0392 0.4250 0.0433 1.0000 Uiso R . . . . . . H402 H 0.6072 0.0551 0.4544 0.0434 1.0000 Uiso R . . . . . . H401 H 0.5559 0.1229 0.3873 0.0435 1.0000 Uiso R . . . . . . H421 H 0.9338 0.1148 0.3016 0.0241 1.0000 Uiso R . . . . . . H431 H 1.0386 0.1488 0.1938 0.0283 1.0000 Uiso R . . . . . . H441 H 0.9284 0.1328 0.0138 0.0296 1.0000 Uiso R . . . . . . H451 H 0.7075 0.0746 -0.0611 0.0271 1.0000 Uiso R . . . . . . H502 H 0.0864 0.6459 0.8234 0.1004 1.0000 Uiso R . . . . . . H501 H 0.1345 0.6057 0.7408 0.1015 1.0000 Uiso R . . . . . . H503 H 0.2305 0.6917 0.8628 0.1012 1.0000 Uiso R . . . . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 K1 0.0232(3) 0.0263(3) 0.0226(3) 0.0084(2) 0.0067(2) 0.0062(2) O2 0.0313(10) 0.0293(9) 0.0249(9) 0.0094(7) 0.0070(7) 0.0106(8) C3 0.0373(15) 0.0325(14) 0.0215(12) 0.0120(11) 0.0109(11) 0.0154(12) C4 0.0373(14) 0.0314(14) 0.0264(12) 0.0133(11) 0.0189(11) 0.0150(12) O5 0.0264(9) 0.0289(9) 0.0232(8) 0.0085(7) 0.0111(7) 0.0083(8) C6 0.0219(12) 0.0239(12) 0.0349(13) 0.0087(11) 0.0134(11) 0.0083(10) C7 0.0234(12) 0.0205(12) 0.0329(13) 0.0024(10) 0.0118(10) 0.0056(10) O8 0.0267(9) 0.0277(9) 0.0226(8) 0.0058(7) 0.0103(7) 0.0107(7) C9 0.0264(13) 0.0379(15) 0.0226(12) 0.0040(11) 0.0058(10) 0.0082(12) C10 0.0307(14) 0.0433(16) 0.0217(12) 0.0080(11) 0.0061(11) 0.0169(12) O11 0.0323(10) 0.0319(10) 0.0302(9) 0.0148(8) 0.0057(8) 0.0136(8) C12 0.0498(17) 0.0378(15) 0.0297(14) 0.0185(12) 0.0165(13) 0.0217(14) C13 0.0507(18) 0.0366(15) 0.0327(14) 0.0188(13) 0.0212(13) 0.0136(14) O14 0.0317(10) 0.0314(9) 0.0293(9) 0.0111(8) 0.0162(8) 0.0108(8) C15 0.0282(14) 0.0309(14) 0.0441(15) 0.0117(12) 0.0225(12) 0.0078(11) C16 0.0224(13) 0.0283(13) 0.0409(15) 0.0083(12) 0.0156(11) 0.0057(11) O17 0.0286(9) 0.0251(9) 0.0275(9) 0.0035(7) 0.0109(7) 0.0071(8) C18 0.0331(14) 0.0277(13) 0.0273(13) -0.0004(11) 0.0081(11) 0.0078(11) C19 0.0336(15) 0.0364(15) 0.0222(12) 0.0041(11) 0.0046(11) 0.0119(12) N20 0.0288(11) 0.0321(11) 0.0254(10) 0.0108(9) 0.0112(9) 0.0167(10) C21 0.0184(11) 0.0248(12) 0.0151(10) 0.0044(9) 0.0075(9) 0.0072(10) B22 0.0172(12) 0.0236(13) 0.0151(12) 0.0062(10) 0.0059(10) 0.0110(11) C23 0.0147(11) 0.0254(12) 0.0170(10) 0.0056(9) 0.0071(9) 0.0072(9) C24 0.0135(10) 0.0259(12) 0.0219(11) 0.0086(10) 0.0068(9) 0.0074(9) C25 0.0204(11) 0.0303(13) 0.0247(12) 0.0143(11) 0.0091(10) 0.0111(10) C26 0.0157(11) 0.0359(14) 0.0196(11) 0.0092(10) 0.0068(9) 0.0079(10) C27 0.0207(12) 0.0254(12) 0.0215(11) 0.0022(10) 0.0093(10) 0.0067(10) C28 0.0174(11) 0.0257(12) 0.0231(11) 0.0072(10) 0.0079(9) 0.0094(10) C29 0.0313(14) 0.0241(13) 0.0254(13) 0.0003(11) 0.0015(11) 0.0110(11) C30 0.0318(14) 0.0441(16) 0.0209(12) 0.0104(12) 0.0052(11) 0.0116(13) C31 0.0250(12) 0.0282(13) 0.0267(12) 0.0119(10) 0.0081(10) 0.0161(11) C32 0.0171(11) 0.0253(12) 0.0188(11) 0.0103(9) 0.0060(9) 0.0121(10) C33 0.0190(11) 0.0290(12) 0.0213(11) 0.0128(10) 0.0083(9) 0.0123(10) C34 0.0227(12) 0.0363(14) 0.0277(12) 0.0178(11) 0.0133(10) 0.0158(11) C35 0.0195(12) 0.0295(13) 0.0246(12) 0.0127(11) 0.0053(10) 0.0082(10) C36 0.0227(12) 0.0245(12) 0.0217(11) 0.0078(10) 0.005(1) 0.0097(10) C37 0.0207(11) 0.0273(12) 0.0192(11) 0.0112(10) 0.0060(9) 0.0137(10) C38 0.0275(13) 0.0237(12) 0.0222(11) 0.0050(10) 0.0093(10) 0.0113(10) C39 0.0233(13) 0.0426(16) 0.0411(16) 0.0142(13) 0.0108(12) 0.0042(12) C40 0.0304(13) 0.0344(14) 0.0245(12) 0.0118(11) 0.0176(11) 0.0166(11) C41 0.0161(11) 0.0178(11) 0.0159(10) 0.0023(9) 0.0043(8) 0.0065(9) C42 0.0164(11) 0.0247(12) 0.0176(11) 0.0038(9) 0.0036(9) 0.0082(10) C43 0.0136(11) 0.0281(13) 0.0259(12) 0.0029(10) 0.0060(9) 0.0058(10) C44 0.0239(12) 0.0278(13) 0.0238(12) 0.0057(10) 0.0140(10) 0.0098(10) C45 0.0232(12) 0.0231(12) 0.0187(11) 0.0053(9) 0.0084(9) 0.0089(10) C46 0.0173(11) 0.0190(11) 0.0203(11) 0.0040(9) 0.0068(9) 0.0080(9) C47 0.0214(10) 0.0256(12) 0.0144(10) 0.0078(9) 0.0073(9) 0.0113(10) N48 0.0640(19) 0.0376(15) 0.0519(16) 0.0112(13) 0.0258(14) 0.0121(14) C49 0.0367(16) 0.0315(15) 0.0340(15) 0.0011(12) 0.0146(12) 0.0094(13) C50 0.086(3) 0.051(2) 0.059(2) 0.0202(18) 0.033(2) 0.038(2) _refine_ls_extinction_method None _oxford_refine_ls_scale 0.3380(4) 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 O2 . C3 . 1.427(3) yes O2 . C19 . 1.422(3) yes C3 . C4 . 1.495(3) yes C3 . H31 . 0.980 no C3 . H32 . 1.001 no C4 . O5 . 1.423(3) yes C4 . H42 . 0.982 no C4 . H41 . 0.982 no O5 . C6 . 1.425(3) yes C6 . C7 . 1.496(3) yes C6 . H62 . 0.987 no C6 . H61 . 0.970 no C7 . O8 . 1.422(3) yes C7 . H71 . 0.983 no C7 . H72 . 0.987 no O8 . C9 . 1.429(3) yes C9 . C10 . 1.493(4) yes C9 . H92 . 0.988 no C9 . H91 . 0.980 no C10 . O11 . 1.420(3) yes C10 . H102 . 0.983 no C10 . H101 . 0.971 no O11 . C12 . 1.411(3) yes C12 . C13 . 1.499(4) yes C12 . H121 . 0.996 no C12 . H122 . 0.983 no C13 . O14 . 1.421(3) yes C13 . H132 . 0.981 no C13 . H131 . 0.982 no O14 . C15 . 1.425(3) yes C15 . C16 . 1.493(4) yes C15 . H151 . 0.979 no C15 . H152 . 0.986 no C16 . O17 . 1.422(3) yes C16 . H162 . 0.974 no C16 . H161 . 0.993 no O17 . C18 . 1.417(3) yes C18 . C19 . 1.493(4) yes C18 . H182 . 0.973 no C18 . H181 . 0.991 no C19 . H191 . 0.984 no C19 . H192 . 0.977 no N20 . C21 . 1.154(3) yes C21 . B22 . 1.632(3) yes B22 . C23 . 1.666(3) yes B22 . C32 . 1.677(3) yes B22 . C41 . 1.657(3) yes C23 . C24 . 1.415(3) yes C23 . C28 . 1.420(3) yes C24 . C25 . 1.396(3) yes C24 . C31 . 1.512(3) yes C25 . C26 . 1.387(3) yes C25 . H251 . 0.945 no C26 . C27 . 1.385(3) yes C26 . C30 . 1.517(3) yes C27 . C28 . 1.400(3) yes C27 . H271 . 0.952 no C28 . C29 . 1.514(3) yes C29 . H291 . 0.981 no C29 . H293 . 0.986 no C29 . H292 . 0.986 no C30 . H301 . 0.963 no C30 . H303 . 0.964 no C30 . H302 . 0.967 no C31 . H311 . 0.965 no C31 . H313 . 0.973 no C31 . H312 . 0.959 no C32 . C33 . 1.434(3) yes C32 . C37 . 1.410(3) yes C33 . C34 . 1.395(3) yes C33 . C40 . 1.506(3) yes C34 . C35 . 1.385(3) yes C34 . H341 . 0.962 no C35 . C36 . 1.382(3) yes C35 . C39 . 1.507(3) yes C36 . C37 . 1.402(3) yes C36 . H361 . 0.955 no C37 . C38 . 1.512(3) yes C38 . H382 . 0.972 no C38 . H381 . 0.982 no C38 . H383 . 0.950 no C39 . H393 . 0.969 no C39 . H392 . 0.965 no C39 . H391 . 0.970 no C40 . H403 . 0.957 no C40 . H402 . 0.956 no C40 . H401 . 0.982 no C41 . C42 . 1.398(3) yes C41 . C46 . 1.421(3) yes C42 . C43 . 1.390(3) yes C42 . H421 . 0.957 no C43 . C44 . 1.378(3) yes C43 . H431 . 0.958 no C44 . C45 . 1.391(3) yes C44 . H441 . 0.952 no C45 . C46 . 1.398(3) yes C45 . H451 . 0.952 no C46 . C47 . 1.436(3) yes C47 . C47 2_655 1.194(4) yes N48 . C49 . 1.137(4) yes C49 . C50 . 1.438(4) yes C50 . H502 . 0.934 no C50 . H501 . 0.959 no C50 . H503 . 0.958 no 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 C3 . O2 . C19 . 110.99(18) yes O2 . C3 . C4 . 109.82(19) yes O2 . C3 . H31 . 108.5 no C4 . C3 . H31 . 108.9 no O2 . C3 . H32 . 109.2 no C4 . C3 . H32 . 109.4 no H31 . C3 . H32 . 110.9 no C3 . C4 . O5 . 108.65(18) yes C3 . C4 . H42 . 110.7 no O5 . C4 . H42 . 110.1 no C3 . C4 . H41 . 109.1 no O5 . C4 . H41 . 108.2 no H42 . C4 . H41 . 110.0 no C4 . O5 . C6 . 113.22(17) yes O5 . C6 . C7 . 108.54(18) yes O5 . C6 . H62 . 110.0 no C7 . C6 . H62 . 108.9 no O5 . C6 . H61 . 109.4 no C7 . C6 . H61 . 109.4 no H62 . C6 . H61 . 110.5 no C6 . C7 . O8 . 109.53(19) yes C6 . C7 . H71 . 110.1 no O8 . C7 . H71 . 110.6 no C6 . C7 . H72 . 108.6 no O8 . C7 . H72 . 109.5 no H71 . C7 . H72 . 108.6 no C7 . O8 . C9 . 112.00(18) yes O8 . C9 . C10 . 108.9(2) yes O8 . C9 . H92 . 108.5 no C10 . C9 . H92 . 110.1 no O8 . C9 . H91 . 110.5 no C10 . C9 . H91 . 109.6 no H92 . C9 . H91 . 109.2 no C9 . C10 . O11 . 107.7(2) yes C9 . C10 . H102 . 110.5 no O11 . C10 . H102 . 110.0 no C9 . C10 . H101 . 109.4 no O11 . C10 . H101 . 110.7 no H102 . C10 . H101 . 108.6 no C10 . O11 . C12 . 115.01(19) yes O11 . C12 . C13 . 107.8(2) yes O11 . C12 . H121 . 110.4 no C13 . C12 . H121 . 111.1 no O11 . C12 . H122 . 109.3 no C13 . C12 . H122 . 110.0 no H121 . C12 . H122 . 108.3 no C12 . C13 . O14 . 109.1(2) yes C12 . C13 . H132 . 109.1 no O14 . C13 . H132 . 109.2 no C12 . C13 . H131 . 109.7 no O14 . C13 . H131 . 108.8 no H132 . C13 . H131 . 110.9 no C13 . O14 . C15 . 112.43(19) yes O14 . C15 . C16 . 109.10(19) yes O14 . C15 . H151 . 111.4 no C16 . C15 . H151 . 108.3 no O14 . C15 . H152 . 109.8 no C16 . C15 . H152 . 109.3 no H151 . C15 . H152 . 108.9 no C15 . C16 . O17 . 108.8(2) yes C15 . C16 . H162 . 110.7 no O17 . C16 . H162 . 109.5 no C15 . C16 . H161 . 109.7 no O17 . C16 . H161 . 110.9 no H162 . C16 . H161 . 107.4 no C16 . O17 . C18 . 112.56(18) yes O17 . C18 . C19 . 109.2(2) yes O17 . C18 . H182 . 110.4 no C19 . C18 . H182 . 109.3 no O17 . C18 . H181 . 108.4 no C19 . C18 . H181 . 109.8 no H182 . C18 . H181 . 109.7 no C18 . C19 . O2 . 109.9(2) yes C18 . C19 . H191 . 107.7 no O2 . C19 . H191 . 109.3 no C18 . C19 . H192 . 109.4 no O2 . C19 . H192 . 109.0 no H191 . C19 . H192 . 111.5 no N20 . C21 . B22 . 177.2(2) yes C21 . B22 . C23 . 112.03(18) yes C21 . B22 . C32 . 102.17(16) yes C23 . B22 . C32 . 109.76(17) yes C21 . B22 . C41 . 100.91(17) yes C23 . B22 . C41 . 111.51(17) yes C32 . B22 . C41 . 119.66(18) yes B22 . C23 . C24 . 119.22(19) yes B22 . C23 . C28 . 125.39(19) yes C24 . C23 . C28 . 115.18(19) yes C23 . C24 . C25 . 121.8(2) yes C23 . C24 . C31 . 122.07(19) yes C25 . C24 . C31 . 116.1(2) yes C24 . C25 . C26 . 122.0(2) yes C24 . C25 . H251 . 118.7 no C26 . C25 . H251 . 119.4 no C25 . C26 . C27 . 116.8(2) yes C25 . C26 . C30 . 121.5(2) yes C27 . C26 . C30 . 121.7(2) yes C26 . C27 . C28 . 122.3(2) yes C26 . C27 . H271 . 120.2 no C28 . C27 . H271 . 117.5 no C23 . C28 . C27 . 121.2(2) yes C23 . C28 . C29 . 123.0(2) yes C27 . C28 . C29 . 115.8(2) yes C28 . C29 . H291 . 109.4 no C28 . C29 . H293 . 109.9 no H291 . C29 . H293 . 107.8 no C28 . C29 . H292 . 111.3 no H291 . C29 . H292 . 108.2 no H293 . C29 . H292 . 110.1 no C26 . C30 . H301 . 109.2 no C26 . C30 . H303 . 110.2 no H301 . C30 . H303 . 109.2 no C26 . C30 . H302 . 109.2 no H301 . C30 . H302 . 109.2 no H303 . C30 . H302 . 109.8 no C24 . C31 . H311 . 110.7 no C24 . C31 . H313 . 110.2 no H311 . C31 . H313 . 109.0 no C24 . C31 . H312 . 111.7 no H311 . C31 . H312 . 107.4 no H313 . C31 . H312 . 107.6 no B22 . C32 . C33 . 116.63(19) yes B22 . C32 . C37 . 127.45(19) yes C33 . C32 . C37 . 115.9(2) yes C32 . C33 . C34 . 120.8(2) yes C32 . C33 . C40 . 123.0(2) yes C34 . C33 . C40 . 116.2(2) yes C33 . C34 . C35 . 122.8(2) yes C33 . C34 . H341 . 118.5 no C35 . C34 . H341 . 118.7 no C34 . C35 . C36 . 116.3(2) yes C34 . C35 . C39 . 121.6(2) yes C36 . C35 . C39 . 122.1(2) yes C35 . C36 . C37 . 123.3(2) yes C35 . C36 . H361 . 117.9 no C37 . C36 . H361 . 118.9 no C32 . C37 . C36 . 120.7(2) yes C32 . C37 . C38 . 124.9(2) yes C36 . C37 . C38 . 114.4(2) yes C37 . C38 . H382 . 109.5 no C37 . C38 . H381 . 112.4 no H382 . C38 . H381 . 109.8 no C37 . C38 . H383 . 111.1 no H382 . C38 . H383 . 107.5 no H381 . C38 . H383 . 106.5 no C35 . C39 . H393 . 109.5 no C35 . C39 . H392 . 109.6 no H393 . C39 . H392 . 109.6 no C35 . C39 . H391 . 110.0 no H393 . C39 . H391 . 110.5 no H392 . C39 . H391 . 107.7 no C33 . C40 . H403 . 111.1 no C33 . C40 . H402 . 110.7 no H403 . C40 . H402 . 106.4 no C33 . C40 . H401 . 113.1 no H403 . C40 . H401 . 107.8 no H402 . C40 . H401 . 107.4 no B22 . C41 . C42 . 121.99(18) yes B22 . C41 . C46 . 122.21(18) yes C42 . C41 . C46 . 115.38(19) yes C41 . C42 . C43 . 123.0(2) yes C41 . C42 . H421 . 118.6 no C43 . C42 . H421 . 118.4 no C42 . C43 . C44 . 120.2(2) yes C42 . C43 . H431 . 120.3 no C44 . C43 . H431 . 119.5 no C43 . C44 . C45 . 119.4(2) yes C43 . C44 . H441 . 120.3 no C45 . C44 . H441 . 120.3 no C44 . C45 . C46 . 120.0(2) yes C44 . C45 . H451 . 121.4 no C46 . C45 . H451 . 118.6 no C41 . C46 . C45 . 121.90(19) yes C41 . C46 . C47 . 120.81(19) yes C45 . C46 . C47 . 117.27(19) yes C46 . C47 . C47 2_655 175.7(3) yes N48 . C49 . C50 . 177.7(3) yes C49 . C50 . H502 . 108.6 no C49 . C50 . H501 . 110.5 no H502 . C50 . H501 . 110.1 no C49 . C50 . H503 . 108.3 no H502 . C50 . H503 . 109.1 no H501 . C50 . H503 . 110.3 no loop_ _geom_hbond_atom_site_label_D _geom_hbond_site_symmetry_D _geom_hbond_atom_site_label_H _geom_hbond_site_symmetry_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_angle_DHA _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_publ_flag C38 . H381 . C41 . 128 0.98 2.46 3.153(4) yes C40 . H401 . C21 . 121 0.98 2.37 3.002(4) yes _chemical_name_common .