# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2010 data_global _journal_coden_Cambridge 177 loop_ _publ_author_name 'Monteiro, Nuno' 'Belot, Sebastien' 'Raffa, Guillaume' 'Balme, Genevieve' _publ_contact_author_name 'Monteiro, Nuno' _publ_contact_author_email monteiro@univ-lyon1.fr _publ_section_title ; ; # Attachment '- CIF 2a_publish.cif' data_2a _database_code_depnum_ccdc_archive 'CCDC 798397' #TrackingRef '- CIF 2a_publish.cif' _exptl_special_details ; The crystal was placed in the cold stream of an Oxford Cryosystems open-flow nitrogen cryostat (Cosier & Glazer, 1986) with a nominal stability of 0.1K. Cosier, J. & Glazer, A.M., 1986. J. Appl. Cryst. 105 107. ; _refine_special_details ; ? ; #--------------------------------------------------------------- # _oxford_ data items, April 2010: # There is some uncertainty about the correct way of forming local data # names, e.g. # _atom_site_special_shape_oxford # or # _oxford_atom_site_special_shape # see: # http://www.iucr.org/resources/cif/spec/version1.1/semantics#namespace # A reserved prefix, e.g. foo, must be used in the following way # " If the data file contains items defined in a DDL1 dictionary, the # local data names assigned under the reserved prefix must contain it as # their first component, e.g. _foo_atom_site_my_item. " # However, this seems to say the opposite: # http://www.iucr.org/__data/iucr/cif/standard/cifstd8.html # According to advice from the IUCr, CRYSTALS is correct #--------------------------------------------------------------- # End of 'script/refcif.dat' #end of refcif _cell_length_a 12.173(2) _cell_length_b 14.445(2) _cell_length_c 8.223(2) _cell_angle_alpha 90 _cell_angle_beta 103.46(2) _cell_angle_gamma 90 _cell_volume 1406.2(5) _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' 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' I -0.4742 1.8119 20.1472 4.3470 18.9949 0.3814 7.5138 27.7660 2.2735 66.8776 4.0712 'International Tables Vol C 4.2.6.8 and 6.1.1.4' Br -0.2901 2.4595 17.1789 2.1723 5.2358 16.5796 5.6377 0.2609 3.9851 41.4328 2.9557 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 4 # Given Formula = C15 H18 Br0.50 I1.50 O3 # Dc = 2.25 Fooo = 752.00 Mu = 48.00 M = 476.61 # Found Formula = C17 H9 I1 O3 # Dc = 1.83 FOOO = 752.00 Mu = 22.84 M = 388.16 _chemical_formula_sum 'C17 H9 I1 O3' _chemical_formula_moiety 'C17 H9 I1 O3' _chemical_compound_source ? _chemical_formula_weight 388.16 _cell_measurement_reflns_used 2573 _cell_measurement_theta_min 3.4346 _cell_measurement_theta_max 29.4921 _cell_measurement_temperature 293 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_min 0.081 _exptl_crystal_size_mid 0.286 _exptl_crystal_size_max 0.520 _exptl_crystal_density_diffrn 1.833 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 752 _exptl_absorpt_coefficient_mu 2.284 # Sheldrick geometric approximatio 0.52 0.83 _exptl_absorpt_correction_T_min 0.471 _exptl_absorpt_correction_T_max 0.869 _exptl_absorpt_correction_type analytical _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET) (compiled Aug 27 2010,11:50:40) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. Reid. (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) ; _diffrn_radiation_wavelength 0.7107 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Atlas, Gemini ultra' _diffrn_detector_area_resol_mean 10.4685 # If a reference occurs more than once, delete the author # and date from subsequent references. _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET) (compiled Aug 27 2010,11:50:40) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET) (compiled Aug 27 2010,11:50:40) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET) (compiled Aug 27 2010,11:50:40) ; _computing_structure_solution 'SIR97 (Altomare et al., 1999)' _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 6630 _reflns_number_total 3327 _diffrn_reflns_av_R_equivalents 0.079 # Number of reflections without Friedels Law is 0 # Number of reflections with Friedels Law is 3327 # Theoretical number of reflections is about 7876 _diffrn_reflns_theta_min 3.442 _diffrn_reflns_theta_max 29.553 _diffrn_measured_fraction_theta_max 0.846 _diffrn_reflns_theta_full 26.302 _diffrn_measured_fraction_theta_full 0.997 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 10 _reflns_limit_h_min -16 _reflns_limit_h_max 16 _reflns_limit_k_min 0 _reflns_limit_k_max 20 _reflns_limit_l_min 0 _reflns_limit_l_max 11 _oxford_diffrn_Wilson_B_factor 4.99 _oxford_diffrn_Wilson_scale 0.15 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -1.99 _refine_diff_density_max 2.39 # 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>-10.0\s(I) _refine_ls_number_reflns 3323 _refine_ls_number_restraints 0 _refine_ls_number_parameters 190 _oxford_refine_ls_R_factor_ref 0.1292 _refine_ls_wR_factor_ref 0.3093 _refine_ls_goodness_of_fit_ref 0.9991 _refine_ls_shift/su_max 0.0001591 _refine_ls_shift/su_mean 0.0000098 # The values computed from all data _oxford_reflns_number_all 3323 _refine_ls_R_factor_all 0.1292 _refine_ls_wR_factor_all 0.3093 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 1974 _refine_ls_R_factor_gt 0.0934 _refine_ls_wR_factor_gt 0.2532 # 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 none # 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^) + ( 0.20P)^2^ + 0.00P] ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 ; # Insert your own references if required - in alphabetical order _publ_section_references ; Altomare, A., Burla, M.C., Camalli, M., Cascarano, G.L., Giacovazzo, C., Guagliardi, A., Grazia, A., Moliterni, G., Polidori, G. & Spagna, R. (1999). J. App. Cryst. 32, 115-119. Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. Oxford Diffraction, (2002). CrysAlis RED. Oxford Diffraction, (2006). Gemini User Manual. 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 _atom_site_attached_hydrogens I1 I 0.37354(6) 0.70698(4) 0.28840(9) 0.0818 1.0000 Uani . . . . . . C2 C 0.3513(6) 0.6043(5) 0.4514(11) 0.0563 1.0000 Uani . . . . . . C3 C 0.2519(6) 0.5458(5) 0.4253(9) 0.0486 1.0000 Uani . . . . . . C4 C 0.1466(7) 0.5395(6) 0.3020(10) 0.0553 1.0000 Uani . . . . . . O5 O 0.1178(5) 0.5905(5) 0.1780(8) 0.0780 1.0000 Uani . . . . . . C6 C 0.0755(6) 0.4615(5) 0.3364(10) 0.0559 1.0000 Uani . . . . . . C7 C 0.1078(6) 0.4080(5) 0.4813(9) 0.0497 1.0000 Uani . . . . . . O8 O 0.2083(4) 0.4201(4) 0.5967(7) 0.0592 1.0000 Uani . . . . . . C9 C 0.2708(6) 0.4875(5) 0.5571(10) 0.0520 1.0000 Uani . . . . . . O10 O 0.3720(4) 0.4996(4) 0.6633(7) 0.0537 1.0000 Uani . . . . . . C11 C 0.4236(6) 0.5736(5) 0.5970(10) 0.0543 1.0000 Uani . . . . . . C12 C 0.5348(7) 0.5975(5) 0.6951(10) 0.0543 1.0000 Uani . . . . . . C13 C 0.6009(7) 0.6680(6) 0.6491(13) 0.0697 1.0000 Uani . . . . . . C14 C 0.7048(8) 0.6884(7) 0.7492(15) 0.0739 1.0000 Uani . . . . . . C15 C 0.7470(8) 0.6401(7) 0.9006(13) 0.0758 1.0000 Uani . . . . . . C16 C 0.6848(8) 0.5693(9) 0.9423(12) 0.0808 1.0000 Uani . . . . . . C17 C 0.5791(7) 0.5489(7) 0.8393(11) 0.0686 1.0000 Uani . . . . . . C18 C 0.0403(7) 0.3339(6) 0.5126(12) 0.0657 1.0000 Uani . . . . . . C19 C -0.0583(8) 0.3156(6) 0.4004(13) 0.0684 1.0000 Uani . . . . . . C20 C -0.0912(8) 0.3689(7) 0.2549(14) 0.0739 1.0000 Uani . . . . . . C21 C -0.0269(7) 0.4408(6) 0.2260(10) 0.0603 1.0000 Uani . . . . . . H131 H 0.5739 0.7011 0.5508 0.0832 1.0000 Uiso R . . . . . H141 H 0.7478 0.7349 0.7172 0.0899 1.0000 Uiso R . . . . . H151 H 0.8158 0.6555 0.9705 0.0909 1.0000 Uiso R . . . . . H161 H 0.7128 0.5341 1.0378 0.0962 1.0000 Uiso R . . . . . H171 H 0.5367 0.5010 0.8713 0.0830 1.0000 Uiso R . . . . . H181 H 0.0626 0.2989 0.6096 0.0779 1.0000 Uiso R . . . . . H191 H -0.1042 0.2676 0.4195 0.0819 1.0000 Uiso R . . . . . H201 H -0.1572 0.3548 0.1768 0.0883 1.0000 Uiso R . . . . . H211 H -0.0520 0.4779 0.1311 0.0730 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 I1 0.0810(6) 0.0785(6) 0.0837(6) 0.0253(3) 0.0143(4) -0.0128(3) C2 0.052(4) 0.043(3) 0.071(5) 0.012(4) 0.009(3) 0.000(3) C3 0.046(4) 0.050(3) 0.051(4) 0.004(3) 0.014(3) 0.003(3) C4 0.053(4) 0.059(4) 0.049(4) 0.003(4) 0.004(3) 0.005(4) O5 0.071(4) 0.084(4) 0.068(4) 0.018(3) -0.004(3) -0.004(3) C6 0.047(4) 0.054(4) 0.061(5) -0.013(4) 0.001(3) 0.009(3) C7 0.048(4) 0.053(4) 0.047(4) -0.011(3) 0.009(3) 0.007(3) O8 0.045(3) 0.063(3) 0.067(3) 0.015(3) 0.007(2) -0.002(2) C9 0.048(4) 0.056(4) 0.054(4) 0.002(3) 0.017(3) 0.010(3) O10 0.044(2) 0.060(3) 0.056(3) 0.011(2) 0.007(2) -0.003(2) C11 0.051(4) 0.058(4) 0.056(4) -0.002(4) 0.016(3) 0.001(3) C12 0.050(4) 0.053(4) 0.060(4) -0.010(3) 0.014(3) -0.006(3) C13 0.054(5) 0.063(5) 0.085(6) 0.004(5) 0.000(4) 0.002(4) C14 0.063(5) 0.068(5) 0.096(7) -0.022(5) 0.029(5) -0.017(5) C15 0.053(5) 0.095(7) 0.075(6) -0.012(5) 0.007(4) -0.013(5) C16 0.064(5) 0.120(9) 0.055(5) -0.010(5) 0.005(4) -0.011(6) C17 0.057(5) 0.092(6) 0.054(5) -0.006(4) 0.008(4) -0.015(4) C18 0.057(5) 0.057(4) 0.080(6) 0.003(4) 0.010(4) -0.012(4) C19 0.058(5) 0.058(4) 0.087(7) 0.001(5) 0.011(4) -0.009(4) C20 0.056(5) 0.075(6) 0.084(6) -0.013(5) 0.002(4) -0.008(4) C21 0.058(4) 0.068(5) 0.051(4) -0.002(4) 0.006(4) 0.002(4) _refine_ls_extinction_method None _oxford_refine_ls_scale 3.74(17) 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 I1 . C2 . 2.059(8) yes C2 . C3 . 1.450(10) yes C2 . C11 . 1.383(11) yes C3 . C4 . 1.440(10) yes C3 . C9 . 1.349(10) yes C4 . O5 . 1.240(10) yes C4 . C6 . 1.488(12) yes C6 . C7 . 1.397(11) yes C6 . C21 . 1.393(10) yes C7 . O8 . 1.374(9) yes C7 . C18 . 1.409(11) yes O8 . C9 . 1.323(10) yes C9 . O10 . 1.345(9) yes O10 . C11 . 1.412(9) yes C11 . C12 . 1.447(11) yes C12 . C13 . 1.403(12) yes C12 . C17 . 1.376(12) yes C13 . C14 . 1.371(13) yes C13 . H131 . 0.930 no C14 . C15 . 1.415(15) yes C14 . H141 . 0.927 no C15 . C16 . 1.363(14) yes C15 . H151 . 0.926 no C16 . C17 . 1.397(12) yes C16 . H161 . 0.931 no C17 . H171 . 0.937 no C18 . C19 . 1.359(12) yes C18 . H181 . 0.930 no C19 . C20 . 1.400(14) yes C19 . H191 . 0.926 no C20 . C21 . 1.354(13) yes C20 . H201 . 0.927 no C21 . H211 . 0.937 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 I1 . C2 . C3 . 123.7(6) yes I1 . C2 . C11 . 129.9(6) yes C3 . C2 . C11 . 106.4(7) yes C2 . C3 . C4 . 135.7(7) yes C2 . C3 . C9 . 105.3(7) yes C4 . C3 . C9 . 118.9(7) yes C3 . C4 . O5 . 125.2(8) yes C3 . C4 . C6 . 112.0(6) yes O5 . C4 . C6 . 122.7(7) yes C4 . C6 . C7 . 121.4(6) yes C4 . C6 . C21 . 120.7(7) yes C7 . C6 . C21 . 117.9(8) yes C6 . C7 . O8 . 123.2(7) yes C6 . C7 . C18 . 121.0(7) yes O8 . C7 . C18 . 115.7(7) yes C7 . O8 . C9 . 113.2(6) yes C3 . C9 . O8 . 131.1(7) yes C3 . C9 . O10 . 113.6(7) yes O8 . C9 . O10 . 115.4(6) yes C9 . O10 . C11 . 105.7(6) yes O10 . C11 . C2 . 109.1(6) yes O10 . C11 . C12 . 114.1(6) yes C2 . C11 . C12 . 136.9(7) yes C11 . C12 . C13 . 122.9(8) yes C11 . C12 . C17 . 119.1(7) yes C13 . C12 . C17 . 117.9(7) yes C12 . C13 . C14 . 120.1(9) yes C12 . C13 . H131 . 119.9 no C14 . C13 . H131 . 120.1 no C13 . C14 . C15 . 121.2(9) yes C13 . C14 . H141 . 119.2 no C15 . C14 . H141 . 119.6 no C14 . C15 . C16 . 118.8(8) yes C14 . C15 . H151 . 121.2 no C16 . C15 . H151 . 120.0 no C15 . C16 . C17 . 119.6(10) yes C15 . C16 . H161 . 120.4 no C17 . C16 . H161 . 120.0 no C16 . C17 . C12 . 122.4(9) yes C16 . C17 . H171 . 118.4 no C12 . C17 . H171 . 119.2 no C7 . C18 . C19 . 119.0(8) yes C7 . C18 . H181 . 120.3 no C19 . C18 . H181 . 120.8 no C18 . C19 . C20 . 120.3(8) yes C18 . C19 . H191 . 120.2 no C20 . C19 . H191 . 119.5 no C19 . C20 . C21 . 120.6(8) yes C19 . C20 . H201 . 120.0 no C21 . C20 . H201 . 119.3 no C6 . C21 . C20 . 121.1(8) yes C6 . C21 . H211 . 119.2 no C20 . C21 . H211 . 119.7 no _iucr_refine_instruction_details_constraints ; # # Punched on 16/09/10 at 15:13:36 # #LIST 12 BLOCK SCALE X'S, U'S RIDE C ( 13,X'S) H ( 131,X'S) RIDE C ( 14,X'S) H ( 141,X'S) RIDE C ( 15,X'S) H ( 151,X'S) RIDE C ( 16,X'S) H ( 161,X'S) RIDE C ( 17,X'S) H ( 171,X'S) RIDE C ( 18,X'S) H ( 181,X'S) RIDE C ( 19,X'S) H ( 191,X'S) RIDE C ( 20,X'S) H ( 201,X'S) RIDE C ( 21,X'S) H ( 211,X'S) END ; _iucr_refine_instruction_details_restraints ; # # Punched on 16/09/10 at 15:13:36 # #LIST 16 NO REM HREST START (DO NOT REMOVE THIS LINE) REM HREST END (DO NOT REMOVE THIS LINE) END ; # Attachment '- CIF 3a_publish.cif' data_3a _database_code_depnum_ccdc_archive 'CCDC 798398' #TrackingRef '- CIF 3a_publish.cif' _exptl_special_details ; The crystal was placed in the cold stream of an Oxford Cryosystems open-flow nitrogen cryostat (Cosier & Glazer, 1986) with a nominal stability of 0.1K. Cosier, J. & Glazer, A.M., 1986. J. Appl. Cryst. 105 107. ; _refine_special_details ; ? ; #--------------------------------------------------------------- # _oxford_ data items, April 2010: # There is some uncertainty about the correct way of forming local data # names, e.g. # _atom_site_special_shape_oxford # or # _oxford_atom_site_special_shape # see: # http://www.iucr.org/resources/cif/spec/version1.1/semantics#namespace # A reserved prefix, e.g. foo, must be used in the following way # " If the data file contains items defined in a DDL1 dictionary, the # local data names assigned under the reserved prefix must contain it as # their first component, e.g. _foo_atom_site_my_item. " # However, this seems to say the opposite: # http://www.iucr.org/__data/iucr/cif/standard/cifstd8.html # According to advice from the IUCr, CRYSTALS is correct #--------------------------------------------------------------- # End of 'script/refcif.dat' #end of refcif _cell_length_a 18.6185(3) _cell_length_b 14.0017(3) _cell_length_c 14.1965(3) _cell_angle_alpha 90 _cell_angle_beta 107.820(2) _cell_angle_gamma 90 _cell_volume 3523.34(13) _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' 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' I -0.4742 1.8119 20.1472 4.3470 18.9949 0.3814 7.5138 27.7660 2.2735 66.8776 4.0712 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 8 # Given Formula = C39 H39 I6.50 O6.50 # Dc = 2.71 Fooo = 2000.00 Mu = 57.82 M = 1436.61 # Found Formula = C36 H24 I4 O6 # Dc = 2.00 FOOO = 2000.00 Mu = 35.81 M = 1060.20 _chemical_formula_sum 'C18 H12 I2 O3' _chemical_formula_moiety 'C18 H12 I2 O3' _chemical_compound_source ? _chemical_formula_weight 530.08 _cell_measurement_reflns_used 22776 _cell_measurement_theta_min 2.9037 _cell_measurement_theta_max 29.1870 _cell_measurement_temperature 293 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_min 0.047 _exptl_crystal_size_mid 0.204 _exptl_crystal_size_max 0.366 _exptl_crystal_density_diffrn 1.999 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 2000 _exptl_absorpt_coefficient_mu 3.581 # Sheldrick geometric approximatio 0.48 0.85 _exptl_absorpt_correction_T_min 0.396 _exptl_absorpt_correction_T_max 0.851 _exptl_absorpt_correction_type analytical _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET) (compiled Aug 27 2010,11:50:40) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. Reid. (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) ; _diffrn_radiation_wavelength 0.7107 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'Mova (Mo) X-ray Source' _diffrn_radiation_monochromator mirror _diffrn_measurement_device_type 'Xcalibur, Eos, Nova' _diffrn_detector_area_resol_mean 15.9897 # If a reference occurs more than once, delete the author # and date from subsequent references. _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET) (compiled Aug 27 2010,11:50:40) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET) (compiled Aug 27 2010,11:50:40) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET) (compiled Aug 27 2010,11:50:40) ; _computing_structure_solution 'SIR97 (Altomare et al., 1999)' _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 48398 _reflns_number_total 8663 _diffrn_reflns_av_R_equivalents 0.032 # Number of reflections without Friedels Law is 0 # Number of reflections with Friedels Law is 8663 # Theoretical number of reflections is about 19185 _diffrn_reflns_theta_min 2.909 _diffrn_reflns_theta_max 29.250 _diffrn_measured_fraction_theta_max 0.903 _diffrn_reflns_theta_full 26.617 _diffrn_measured_fraction_theta_full 0.999 _diffrn_reflns_limit_h_min -25 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _reflns_limit_h_min -25 _reflns_limit_h_max 24 _reflns_limit_k_min 0 _reflns_limit_k_max 19 _reflns_limit_l_min 0 _reflns_limit_l_max 19 _oxford_diffrn_Wilson_B_factor 4.52 _oxford_diffrn_Wilson_scale 0.95 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -1.07 _refine_diff_density_max 1.59 # 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>-10.0\s(I) _refine_ls_number_reflns 8663 _refine_ls_number_restraints 1 _refine_ls_number_parameters 415 _oxford_refine_ls_R_factor_ref 0.0487 _refine_ls_wR_factor_ref 0.0755 _refine_ls_goodness_of_fit_ref 1.0021 _refine_ls_shift/su_max 0.0010108 _refine_ls_shift/su_mean 0.0000388 # The values computed from all data _oxford_reflns_number_all 8663 _refine_ls_R_factor_all 0.0487 _refine_ls_wR_factor_all 0.0755 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 6820 _refine_ls_R_factor_gt 0.0343 _refine_ls_wR_factor_gt 0.0674 # 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 none # 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^) + ( 0.02P)^2^ + 8.27P] ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 ; # Insert your own references if required - in alphabetical order _publ_section_references ; Altomare, A., Burla, M.C., Camalli, M., Cascarano, G.L., Giacovazzo, C., Guagliardi, A., Grazia, A., Moliterni, G., Polidori, G. & Spagna, R. (1999). J. App. Cryst. 32, 115-119. Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. Oxford Diffraction, (2002). CrysAlis RED. Oxford Diffraction, (2002). Xcalibur User Manual. 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 _atom_site_attached_hydrogens I1 I 0.813302(17) -0.06559(2) 0.45619(2) 0.0599 1.0000 Uani . . . . . . C2 C 0.7755(2) -0.1428(3) 0.5598(3) 0.0556 1.0000 Uani . . . . . . C3 C 0.8264(2) -0.1757(3) 0.6375(3) 0.0545 1.0000 Uani . . . . . . I4 I 0.788789(17) -0.25467(2) 0.74486(2) 0.0669 1.0000 Uani . . . . . . C5 C 0.9096(2) -0.1718(3) 0.6625(3) 0.0440 1.0000 Uani . . . . . . C6 C 0.9424(2) -0.2613(3) 0.6440(3) 0.0474 1.0000 Uani . . . . . . O7 O 1.01928(15) -0.26743(18) 0.6649(2) 0.0498 1.0000 Uani . . . . . . C8 C 1.0648(2) -0.1896(3) 0.6963(3) 0.0433 1.0000 Uani . . . . . . C9 C 1.0359(2) -0.1033(3) 0.7153(3) 0.0444 1.0000 Uani . . . . . . C10 C 0.9553(2) -0.0963(3) 0.6995(3) 0.0449 1.0000 Uani . . . . . . O11 O 0.93596(17) -0.0101(2) 0.7235(3) 0.0664 1.0000 Uani . . . . . . C12 C 0.8680(3) 0.0090(4) 0.7461(4) 0.0761 1.0000 Uani . . . . . . H123 H 0.8753 0.0649 0.7857 0.1137 1.0000 Uiso R . . . . . H122 H 0.8565 -0.0438 0.7814 0.1138 1.0000 Uiso R . . . . . H121 H 0.8275 0.0188 0.6856 0.1139 1.0000 Uiso R . . . . . C13 C 1.0868(2) -0.0278(3) 0.7509(3) 0.0552 1.0000 Uani . . . . . . C14 C 1.1621(3) -0.0402(3) 0.7647(3) 0.0604 1.0000 Uani . . . . . . C15 C 1.1896(2) -0.1270(3) 0.7440(3) 0.0593 1.0000 Uani . . . . . . C16 C 1.1410(2) -0.2023(3) 0.7100(3) 0.0544 1.0000 Uani . . . . . . H161 H 1.1583 -0.2604 0.6952 0.0653 1.0000 Uiso R . . . . . H151 H 1.2409 -0.1343 0.7529 0.0713 1.0000 Uiso R . . . . . H141 H 1.1948 0.0101 0.7893 0.0721 1.0000 Uiso R . . . . . H131 H 1.0684 0.0299 0.7655 0.0656 1.0000 Uiso R . . . . . O17 O 0.90708(17) -0.3323(2) 0.6115(2) 0.0642 1.0000 Uani . . . . . . C18 C 0.6923(2) -0.1512(3) 0.5364(3) 0.0609 1.0000 Uani D . . . . . C19 C 0.6518(3) -0.0792(5) 0.5563(5) 0.0964 1.0000 Uani . . . . . . C20 C 0.5755(4) -0.0878(7) 0.5396(6) 0.1286 1.0000 Uani . . . . . . C21 C 0.5390(3) -0.1697(7) 0.4999(5) 0.1107 1.0000 Uani . . . . . . C22 C 0.5779(3) -0.2411(6) 0.4782(6) 0.1174 1.0000 Uani . . . . . . C23 C 0.6547(3) -0.2349(3) 0.4953(6) 0.1059 1.0000 Uani D . . . . . H231 H 0.6819 -0.2846 0.4798 0.1272 1.0000 Uiso R . . . . . H221 H 0.5534 -0.2966 0.4505 0.1412 1.0000 Uiso R . . . . . H211 H 0.4875 -0.1753 0.4883 0.1330 1.0000 Uiso R . . . . . H201 H 0.5483 -0.0383 0.5564 0.1540 1.0000 Uiso R . . . . . H191 H 0.6765 -0.0226 0.5814 0.1161 1.0000 Uiso R . . . . . I24 I 0.661338(16) 0.34657(2) 0.23101(2) 0.0642 1.0000 Uani . . . . . . C25 C 0.6176(2) 0.3985(3) 0.3427(3) 0.0579 1.0000 Uani . . . . . . C26 C 0.5411(2) 0.4429(4) 0.3010(3) 0.0601 1.0000 Uani . . . . . . C27 C 0.5335(3) 0.5352(4) 0.2713(5) 0.0942 1.0000 Uani . . . . . . C28 C 0.4629(4) 0.5745(5) 0.2240(5) 0.1030 1.0000 Uani . . . . . . C29 C 0.4014(3) 0.5223(6) 0.2087(4) 0.0905 1.0000 Uani . . . . . . C30 C 0.4059(3) 0.4310(6) 0.2402(5) 0.0965 1.0000 Uani . . . . . . C31 C 0.4766(3) 0.3902(4) 0.2881(4) 0.0852 1.0000 Uani . . . . . . H311 H 0.4798 0.3272 0.3109 0.1019 1.0000 Uiso R . . . . . H301 H 0.3626 0.3951 0.2296 0.1160 1.0000 Uiso R . . . . . H291 H 0.3544 0.5487 0.1754 0.1090 1.0000 Uiso R . . . . . H281 H 0.4590 0.6370 0.2022 0.1243 1.0000 Uiso R . . . . . H271 H 0.5762 0.5730 0.2834 0.1130 1.0000 Uiso R . . . . . C32 C 0.6574(2) 0.3893(3) 0.4343(3) 0.0582 1.0000 Uani . . . . . . I33 I 0.609512(17) 0.43616(3) 0.54628(2) 0.0725 1.0000 Uani . . . . . . C34 C 0.7329(2) 0.3453(3) 0.4733(3) 0.0501 1.0000 Uani . . . . . . C35 C 0.7315(2) 0.2463(3) 0.5073(3) 0.0594 1.0000 Uani . . . . . . O36 O 0.79824(17) 0.1990(2) 0.5420(2) 0.0640 1.0000 Uani . . . . . . C37 C 0.8655(2) 0.2409(3) 0.5462(3) 0.0515 1.0000 Uani . . . . . . C38 C 0.8697(2) 0.3341(3) 0.5188(3) 0.0469 1.0000 Uani . . . . . . C39 C 0.7998(2) 0.3873(3) 0.4809(3) 0.0464 1.0000 Uani . . . . . . O40 O 0.81202(17) 0.4761(2) 0.4545(3) 0.0718 1.0000 Uani . . . . . . C41 C 0.7631(3) 0.5534(3) 0.4524(4) 0.0779 1.0000 Uani . . . . . . H411 H 0.7916 0.6118 0.4610 0.1167 1.0000 Uiso R . . . . . H413 H 0.7416 0.5465 0.5049 0.1172 1.0000 Uiso R . . . . . H412 H 0.7243 0.5546 0.3906 0.1170 1.0000 Uiso R . . . . . C42 C 0.9412(2) 0.3731(4) 0.5280(3) 0.0591 1.0000 Uani . . . . . . C43 C 1.0039(2) 0.3172(5) 0.5618(3) 0.0720 1.0000 Uani . . . . . . C44 C 0.9981(3) 0.2236(5) 0.5868(4) 0.0761 1.0000 Uani . . . . . . C45 C 0.9297(3) 0.1846(4) 0.5795(3) 0.0696 1.0000 Uani . . . . . . H451 H 0.9250 0.1213 0.5963 0.0830 1.0000 Uiso R . . . . . H441 H 1.0412 0.1863 0.6090 0.0909 1.0000 Uiso R . . . . . H431 H 1.0509 0.3428 0.5674 0.0859 1.0000 Uiso R . . . . . H421 H 0.9447 0.4366 0.5118 0.0709 1.0000 Uiso R . . . . . O46 O 0.6752(2) 0.2034(3) 0.5067(3) 0.0884 1.0000 Uani . . . . . . 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 I1 0.06486(17) 0.06697(19) 0.04490(15) 0.00564(13) 0.01250(12) 0.00512(14) C2 0.061(2) 0.047(2) 0.056(2) -0.0035(19) 0.014(2) 0.0004(19) C3 0.053(2) 0.048(2) 0.058(2) -0.0007(19) 0.0109(19) 0.0001(18) I4 0.06028(17) 0.0715(2) 0.0696(2) 0.01632(15) 0.02092(14) -0.00786(15) C5 0.0452(19) 0.045(2) 0.0382(19) 0.0045(16) 0.0066(15) 0.0010(16) C6 0.051(2) 0.047(2) 0.042(2) 0.0001(17) 0.0110(16) -0.0041(17) O7 0.0494(14) 0.0436(15) 0.0539(16) -0.0076(12) 0.0120(12) -0.0008(12) C8 0.050(2) 0.043(2) 0.0353(18) 0.0009(15) 0.0106(15) -0.0040(16) C9 0.050(2) 0.043(2) 0.0366(18) 0.0060(16) 0.0080(15) -0.0026(16) C10 0.052(2) 0.0365(19) 0.044(2) 0.0032(16) 0.0107(16) 0.0036(16) O11 0.0628(18) 0.0418(16) 0.096(2) -0.0074(16) 0.0256(17) 0.0040(14) C12 0.087(3) 0.060(3) 0.092(4) -0.021(3) 0.043(3) 0.002(3) C13 0.065(3) 0.043(2) 0.054(2) 0.0026(18) 0.0130(19) -0.0087(19) C14 0.060(3) 0.061(3) 0.056(3) 0.004(2) 0.012(2) -0.020(2) C15 0.048(2) 0.075(3) 0.054(2) 0.006(2) 0.0146(18) -0.005(2) C16 0.050(2) 0.059(3) 0.054(2) -0.001(2) 0.0172(18) 0.0016(19) O17 0.0627(18) 0.0501(17) 0.077(2) -0.0161(15) 0.0174(15) -0.0142(14) C18 0.051(2) 0.066(3) 0.058(3) -0.007(2) 0.0065(19) 0.010(2) C19 0.068(3) 0.095(4) 0.117(5) -0.029(4) 0.016(3) 0.021(3) C20 0.071(4) 0.159(8) 0.143(7) -0.029(6) 0.014(4) 0.044(5) C21 0.045(3) 0.179(8) 0.100(5) 0.020(5) 0.011(3) 0.023(4) C22 0.059(3) 0.124(6) 0.154(7) -0.021(5) 0.010(4) -0.021(4) C23 0.059(3) 0.081(4) 0.163(7) -0.043(4) 0.012(4) 0.000(3) I24 0.05662(16) 0.0869(2) 0.04922(15) -0.00577(14) 0.01650(12) 0.01869(15) C25 0.048(2) 0.064(3) 0.061(3) -0.002(2) 0.0155(19) 0.000(2) C26 0.0389(19) 0.078(3) 0.056(2) -0.009(2) 0.0042(17) 0.010(2) C27 0.057(3) 0.081(4) 0.137(6) 0.019(4) 0.018(3) 0.014(3) C28 0.083(4) 0.101(5) 0.121(5) 0.030(4) 0.026(4) 0.039(4) C29 0.057(3) 0.137(6) 0.068(3) -0.005(4) 0.006(2) 0.034(4) C30 0.042(3) 0.139(6) 0.097(4) -0.027(4) 0.004(3) -0.003(3) C31 0.047(2) 0.090(4) 0.108(4) -0.011(3) 0.007(3) 0.001(3) C32 0.045(2) 0.068(3) 0.061(3) 0.001(2) 0.0162(19) 0.000(2) I33 0.05157(16) 0.1178(3) 0.05123(16) -0.00647(17) 0.02027(13) 0.01716(17) C34 0.0415(19) 0.060(2) 0.048(2) 0.0026(19) 0.0117(16) 0.0039(18) C35 0.051(2) 0.061(3) 0.065(3) 0.006(2) 0.017(2) 0.001(2) O36 0.0618(18) 0.0542(18) 0.073(2) 0.0129(15) 0.0164(15) 0.0059(15) C37 0.048(2) 0.064(3) 0.040(2) -0.0009(18) 0.0087(16) 0.0086(19) C38 0.0408(18) 0.064(3) 0.0339(18) -0.0035(17) 0.0087(14) 0.0053(17) C39 0.0411(18) 0.052(2) 0.045(2) 0.0057(17) 0.0121(15) 0.0050(16) O40 0.0615(18) 0.0557(19) 0.105(3) 0.0201(18) 0.0354(18) 0.0065(15) C41 0.071(3) 0.050(3) 0.106(4) 0.008(3) 0.018(3) 0.000(2) C42 0.049(2) 0.079(3) 0.049(2) -0.003(2) 0.0153(18) -0.002(2) C43 0.039(2) 0.123(5) 0.052(3) -0.013(3) 0.0110(18) 0.006(3) C44 0.058(3) 0.106(4) 0.057(3) -0.004(3) 0.007(2) 0.033(3) C45 0.071(3) 0.071(3) 0.061(3) 0.003(2) 0.012(2) 0.020(3) O46 0.063(2) 0.077(2) 0.127(3) 0.021(2) 0.032(2) -0.0125(18) _refine_ls_extinction_method None _oxford_refine_ls_scale 1.406(3) 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 I1 . C2 . 2.112(4) yes C2 . C3 . 1.300(6) yes C2 . C18 . 1.486(6) yes C3 . I4 . 2.166(4) yes C3 . C5 . 1.481(5) yes C5 . C6 . 1.453(5) yes C5 . C10 . 1.358(5) yes C6 . O7 . 1.372(5) yes C6 . O17 . 1.202(4) yes O7 . C8 . 1.368(4) yes C8 . C9 . 1.383(5) yes C8 . C16 . 1.384(5) yes C9 . C10 . 1.450(5) yes C9 . C13 . 1.407(5) yes C10 . O11 . 1.333(5) yes O11 . C12 . 1.423(5) yes C12 . H123 . 0.948 no C12 . H122 . 0.954 no C12 . H121 . 0.964 no C13 . C14 . 1.366(6) yes C13 . H131 . 0.925 no C14 . C15 . 1.385(7) yes C14 . H141 . 0.926 no C15 . C16 . 1.376(6) yes C15 . H151 . 0.931 no C16 . H161 . 0.923 no C18 . C19 . 1.339(7) yes C18 . C23 . 1.398(7) yes C19 . C20 . 1.372(9) yes C19 . H191 . 0.931 no C20 . C21 . 1.363(10) yes C20 . H201 . 0.932 no C21 . C22 . 1.325(10) yes C21 . H211 . 0.927 no C22 . C23 . 1.377(8) yes C22 . H221 . 0.925 no C23 . H231 . 0.926 no I24 . C25 . 2.120(4) yes C25 . C26 . 1.499(6) yes C25 . C32 . 1.292(6) yes C26 . C27 . 1.353(7) yes C26 . C31 . 1.374(7) yes C27 . C28 . 1.392(7) yes C27 . H271 . 0.926 no C28 . C29 . 1.320(9) yes C28 . H281 . 0.924 no C29 . C30 . 1.348(9) yes C29 . H291 . 0.934 no C30 . C31 . 1.405(7) yes C30 . H301 . 0.923 no C31 . H311 . 0.935 no C32 . I33 . 2.150(4) yes C32 . C34 . 1.479(5) yes C34 . C35 . 1.470(6) yes C34 . C39 . 1.352(5) yes C35 . O36 . 1.360(5) yes C35 . O46 . 1.206(5) yes O36 . C37 . 1.369(5) yes C37 . C38 . 1.369(6) yes C37 . C45 . 1.388(6) yes C38 . C39 . 1.452(5) yes C38 . C42 . 1.409(5) yes C39 . O40 . 1.338(5) yes O40 . C41 . 1.409(5) yes C41 . H411 . 0.963 no C41 . H413 . 0.953 no C41 . H412 . 0.950 no C42 . C43 . 1.366(6) yes C42 . H421 . 0.926 no C43 . C44 . 1.370(8) yes C43 . H431 . 0.925 no C44 . C45 . 1.361(7) yes C44 . H441 . 0.928 no C45 . H451 . 0.928 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 I1 . C2 . C3 . 117.4(3) yes I1 . C2 . C18 . 115.6(3) yes C3 . C2 . C18 . 127.0(4) yes C2 . C3 . I4 . 118.0(3) yes C2 . C3 . C5 . 128.9(4) yes I4 . C3 . C5 . 113.0(3) yes C3 . C5 . C6 . 113.0(3) yes C3 . C5 . C10 . 127.4(4) yes C6 . C5 . C10 . 119.6(3) yes C5 . C6 . O7 . 118.8(3) yes C5 . C6 . O17 . 124.8(4) yes O7 . C6 . O17 . 116.3(4) yes C6 . O7 . C8 . 121.4(3) yes O7 . C8 . C9 . 121.3(3) yes O7 . C8 . C16 . 116.7(3) yes C9 . C8 . C16 . 121.9(4) yes C8 . C9 . C10 . 118.4(3) yes C8 . C9 . C13 . 117.8(4) yes C10 . C9 . C13 . 123.8(4) yes C9 . C10 . C5 . 120.2(3) yes C9 . C10 . O11 . 111.7(3) yes C5 . C10 . O11 . 128.1(4) yes C10 . O11 . C12 . 123.8(3) yes O11 . C12 . H123 . 108.2 no O11 . C12 . H122 . 109.3 no H123 . C12 . H122 . 110.0 no O11 . C12 . H121 . 109.4 no H123 . C12 . H121 . 110.0 no H122 . C12 . H121 . 109.8 no C9 . C13 . C14 . 120.4(4) yes C9 . C13 . H131 . 118.8 no C14 . C13 . H131 . 120.8 no C13 . C14 . C15 . 120.7(4) yes C13 . C14 . H141 . 119.0 no C15 . C14 . H141 . 120.3 no C14 . C15 . C16 . 120.1(4) yes C14 . C15 . H151 . 119.8 no C16 . C15 . H151 . 120.1 no C8 . C16 . C15 . 119.1(4) yes C8 . C16 . H161 . 119.7 no C15 . C16 . H161 . 121.1 no C2 . C18 . C19 . 120.6(4) yes C2 . C18 . C23 . 120.9(4) yes C19 . C18 . C23 . 118.4(5) yes C18 . C19 . C20 . 121.1(6) yes C18 . C19 . H191 . 118.6 no C20 . C19 . H191 . 120.3 no C19 . C20 . C21 . 120.3(6) yes C19 . C20 . H201 . 120.3 no C21 . C20 . H201 . 119.4 no C20 . C21 . C22 . 119.5(6) yes C20 . C21 . H211 . 120.2 no C22 . C21 . H211 . 120.3 no C21 . C22 . C23 . 121.5(6) yes C21 . C22 . H221 . 119.9 no C23 . C22 . H221 . 118.6 no C18 . C23 . C22 . 119.1(5) yes C18 . C23 . H231 . 119.2 no C22 . C23 . H231 . 121.6 no I24 . C25 . C26 . 112.5(3) yes I24 . C25 . C32 . 119.0(3) yes C26 . C25 . C32 . 128.5(4) yes C25 . C26 . C27 . 121.1(4) yes C25 . C26 . C31 . 121.0(5) yes C27 . C26 . C31 . 117.9(5) yes C26 . C27 . C28 . 121.4(6) yes C26 . C27 . H271 . 119.1 no C28 . C27 . H271 . 119.5 no C27 . C28 . C29 . 120.3(6) yes C27 . C28 . H281 . 120.2 no C29 . C28 . H281 . 119.5 no C28 . C29 . C30 . 120.4(5) yes C28 . C29 . H291 . 119.8 no C30 . C29 . H291 . 119.7 no C29 . C30 . C31 . 120.1(6) yes C29 . C30 . H301 . 120.0 no C31 . C30 . H301 . 119.9 no C30 . C31 . C26 . 119.8(6) yes C30 . C31 . H311 . 120.2 no C26 . C31 . H311 . 120.0 no C25 . C32 . I33 . 118.3(3) yes C25 . C32 . C34 . 127.3(4) yes I33 . C32 . C34 . 114.3(3) yes C32 . C34 . C35 . 113.9(4) yes C32 . C34 . C39 . 126.5(4) yes C35 . C34 . C39 . 119.5(4) yes C34 . C35 . O36 . 118.1(4) yes C34 . C35 . O46 . 124.7(4) yes O36 . C35 . O46 . 117.2(4) yes C35 . O36 . C37 . 122.0(3) yes O36 . C37 . C38 . 121.8(3) yes O36 . C37 . C45 . 116.9(4) yes C38 . C37 . C45 . 121.4(4) yes C37 . C38 . C39 . 118.2(4) yes C37 . C38 . C42 . 118.5(4) yes C39 . C38 . C42 . 123.3(4) yes C38 . C39 . C34 . 120.3(4) yes C38 . C39 . O40 . 111.8(3) yes C34 . C39 . O40 . 127.8(4) yes C39 . O40 . C41 . 123.8(3) yes O40 . C41 . H411 . 108.7 no O40 . C41 . H413 . 109.2 no H411 . C41 . H413 . 109.5 no O40 . C41 . H412 . 109.7 no H411 . C41 . H412 . 109.7 no H413 . C41 . H412 . 110.0 no C38 . C42 . C43 . 119.5(5) yes C38 . C42 . H421 . 119.1 no C43 . C42 . H421 . 121.4 no C42 . C43 . C44 . 120.9(5) yes C42 . C43 . H431 . 119.4 no C44 . C43 . H431 . 119.7 no C43 . C44 . C45 . 120.6(4) yes C43 . C44 . H441 . 119.9 no C45 . C44 . H441 . 119.5 no C37 . C45 . C44 . 119.1(5) yes C37 . C45 . H451 . 119.5 no C44 . C45 . H451 . 121.5 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 . O17 3_756 145 0.93 2.55 3.345(7) yes C45 . H451 . O11 . 152 0.93 2.54 3.388(7) yes _iucr_refine_instruction_details_constraints ; # # Punched on 21/10/10 at 10:37:04 # #LIST 12 BLOCK SCALE X'S, U'S RIDE C ( 12,X'S) H ( 123,X'S) H ( 122,X'S) H ( 121,X'S) RIDE C ( 13,X'S) H ( 131,X'S) RIDE C ( 14,X'S) H ( 141,X'S) RIDE C ( 15,X'S) H ( 151,X'S) RIDE C ( 16,X'S) H ( 161,X'S) RIDE C ( 19,X'S) H ( 191,X'S) RIDE C ( 20,X'S) H ( 201,X'S) RIDE C ( 21,X'S) H ( 211,X'S) RIDE C ( 22,X'S) H ( 221,X'S) RIDE C ( 23,X'S) H ( 231,X'S) RIDE C ( 27,X'S) H ( 271,X'S) RIDE C ( 28,X'S) H ( 281,X'S) RIDE C ( 29,X'S) H ( 291,X'S) RIDE C ( 30,X'S) H ( 301,X'S) RIDE C ( 31,X'S) H ( 311,X'S) RIDE C ( 41,X'S) H ( 411,X'S) H ( 413,X'S) H ( 412,X'S) RIDE C ( 42,X'S) H ( 421,X'S) RIDE C ( 43,X'S) H ( 431,X'S) RIDE C ( 44,X'S) H ( 441,X'S) RIDE C ( 45,X'S) H ( 451,X'S) END ; _iucr_refine_instruction_details_restraints ; # # Punched on 21/10/10 at 10:37:04 # #LIST 16 NO REM HREST START (DO NOT REMOVE THIS LINE) REM HREST END (DO NOT REMOVE THIS LINE) DISTANCE 1.400000 , 0.0010000 = C(18) TO C(23) END ;