# Supplementary Material (ESI) for Organic and Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2010 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 _publ_contact_author_name 'Jeremy Robertson' _publ_contact_author_email JEREMY.ROBERTSON@CHEM.OX.AC.UK _publ_section_title ; Structure and reactivity of bicyclic methylene aziridines prepared by intramolecular aziridination of allenes ; loop_ _publ_author_name 'Jeremy Robertson' 'Tim Claridge' 'George C. Feast' 'Victoria A. Steadman' 'Louise V. White' # Attachment 'Combined.cif' #============================================================================== data_12 _database_code_depnum_ccdc_archive 'CCDC 767254' #TrackingRef 'Combined.cif' #============================================================================== _audit_creation_date 08-09-05 _audit_creation_method CRYSTALS_ver_12.85 _ccdc_journal_depnumber ? _oxford_structure_analysis_title 3-08 _chemical_name_systematic . _chemical_melting_point 357 _cell_length_a 11.8660(3) _cell_length_b 9.5726(3) _cell_length_c 12.1209(4) _cell_angle_alpha 90 _cell_angle_beta 115.3492(11) _cell_angle_gamma 90 _cell_volume 1244.23(7) _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 1 21/n 1 ' _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z -x+1/2,y+1/2,-z+1/2 x+1/2,-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' 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 4 # Given Formula = C16 H13 N1 O2 # Dc = 1.34 Fooo = 528.00 Mu = 0.89 M = 251.28 # Found Formula = C16 H13 N1 O2 # Dc = 1.34 FOOO = 528.00 Mu = 0.89 M = 251.28 _chemical_formula_sum 'C16 H13 N1 O2' _chemical_formula_moiety 'C16 H13 N1 O2' _chemical_compound_source . _chemical_formula_weight 251.28 _cell_measurement_reflns_used 2785 _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 0.10 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_max 0.20 _exptl_crystal_density_diffrn 1.341 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 528 _exptl_absorpt_coefficient_mu 0.089 # Sheldrick geometric approximatio 0.98 0.99 # No experimental values of Tmin/max available _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _exptl_absorpt_correction_T_min 0.98 _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_type 'Nonius KappaCCD' _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 5213 _reflns_number_total 2766 _diffrn_reflns_av_R_equivalents 0.030 # Number of reflections with Friedels Law is 2766 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 2830 _diffrn_reflns_theta_min 5.658 _diffrn_reflns_theta_max 27.401 _diffrn_measured_fraction_theta_max 0.976 _diffrn_reflns_theta_full 26.853 _diffrn_measured_fraction_theta_full 0.977 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _reflns_limit_h_min -15 _reflns_limit_h_max 13 _reflns_limit_k_min 0 _reflns_limit_k_max 12 _reflns_limit_l_min 0 _reflns_limit_l_max 15 _oxford_diffrn_Wilson_B_factor 2.90 _oxford_diffrn_Wilson_scale 0.91 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.30 _refine_diff_density_max 0.34 # 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 2765 _refine_ls_number_restraints 0 _refine_ls_number_parameters 172 _oxford_refine_ls_R_factor_ref 0.0693 _refine_ls_wR_factor_ref 0.1402 _refine_ls_goodness_of_fit_ref 0.9139 _refine_ls_shift/su_max 0.000319 # The values computed from all data _oxford_reflns_number_all 2766 _refine_ls_R_factor_all 0.0694 _refine_ls_wR_factor_all 0.1408 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 1990 _refine_ls_R_factor_gt 0.0448 _refine_ls_wR_factor_gt 0.1201 # 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^) + ( 0.10P)^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., Cascarano, G., Giacovazzo, G., 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 O1 O 0.47455(9) 0.73045(12) 0.81376(9) 0.0339 1.0000 Uani . . . . . . . C2 C 0.57679(14) 0.77949(16) 0.80429(13) 0.0325 1.0000 Uani . . . . . . . O3 O 0.66609(10) 0.82285(13) 0.89016(10) 0.0424 1.0000 Uani . . . . . . . N4 N 0.56633(11) 0.77148(14) 0.68230(11) 0.0346 1.0000 Uani . . . . . . . C5 C 0.44122(13) 0.69978(18) 0.61046(13) 0.0343 1.0000 Uani . . . . . . . C6 C 0.55691(13) 0.62560(18) 0.64668(13) 0.0336 1.0000 Uani . . . . . . . C7 C 0.62647(15) 0.51469(19) 0.66113(15) 0.0408 1.0000 Uani . . . . . . . C8 C 0.37746(12) 0.68898(17) 0.69501(13) 0.0314 1.0000 Uani . . . . . . . C9 C 0.32808(14) 0.54432(17) 0.70320(14) 0.0346 1.0000 Uani . . . . . . . C10 C 0.26221(13) 0.54250(16) 0.78627(13) 0.0319 1.0000 Uani . . . . . . . C11 C 0.13746(12) 0.59475(16) 0.74487(12) 0.0294 1.0000 Uani . . . . . . . C12 C 0.08293(14) 0.60093(16) 0.82997(13) 0.0336 1.0000 Uani . . . . . . . C13 C 0.15323(16) 0.55544(18) 0.95182(14) 0.0401 1.0000 Uani . . . . . . . C14 C 0.27014(16) 0.50402(18) 0.98765(14) 0.0418 1.0000 Uani . . . . . . . C15 C 0.32400(14) 0.49663(17) 0.90446(15) 0.0379 1.0000 Uani . . . . . . . C16 C -0.04000(16) 0.65343(18) 0.78928(16) 0.0409 1.0000 Uani . . . . . . . C17 C -0.10646(16) 0.6974(2) 0.67274(17) 0.0444 1.0000 Uani . . . . . . . C18 C -0.05394(14) 0.68919(19) 0.58827(15) 0.0397 1.0000 Uani . . . . . . . C19 C 0.06466(14) 0.63993(17) 0.62352(14) 0.0344 1.0000 Uani . . . . . . . H51 H 0.3920 0.7324 0.5266 0.0402 1.0000 Uiso R . . . . . . H71 H 0.7143 0.5176 0.7078 0.0527 1.0000 Uiso R . . . . . . H72 H 0.5839 0.4289 0.6199 0.0513 1.0000 Uiso R . . . . . . H81 H 0.3092 0.7574 0.6714 0.0368 1.0000 Uiso R . . . . . . H91 H 0.4003 0.4779 0.7341 0.0449 1.0000 Uiso R . . . . . . H92 H 0.2714 0.5161 0.6221 0.0426 1.0000 Uiso R . . . . . . H131 H 0.1158 0.5627 1.0115 0.0505 1.0000 Uiso R . . . . . . H141 H 0.3198 0.4744 1.0738 0.0477 1.0000 Uiso R . . . . . . H151 H 0.4059 0.4588 0.9328 0.0408 1.0000 Uiso R . . . . . . H161 H -0.0774 0.6574 0.8468 0.0531 1.0000 Uiso R . . . . . . H171 H -0.1909 0.7367 0.6435 0.0546 1.0000 Uiso R . . . . . . H181 H -0.1025 0.7202 0.5019 0.0456 1.0000 Uiso R . . . . . . H191 H 0.0993 0.6361 0.5631 0.0401 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 O1 0.0323(5) 0.0375(6) 0.0340(6) -0.0034(4) 0.0162(4) -0.0054(5) C2 0.0333(7) 0.0291(7) 0.0368(8) 0.0007(6) 0.0167(6) -0.0018(6) O3 0.0386(6) 0.0429(7) 0.0413(6) -0.0058(5) 0.0130(5) -0.0106(5) N4 0.0336(7) 0.0359(7) 0.0368(7) 0.0008(5) 0.0174(5) -0.0023(6) C5 0.0313(7) 0.0386(8) 0.0316(7) 0.0007(6) 0.0123(6) 0.0014(6) C6 0.0332(7) 0.0386(9) 0.0323(7) -0.0011(6) 0.0173(6) -0.0007(7) C7 0.0381(8) 0.0449(10) 0.0440(9) -0.0012(7) 0.0220(7) 0.0044(8) C8 0.0253(7) 0.0343(8) 0.0333(7) -0.0022(6) 0.0113(5) 0.0020(6) C9 0.0284(7) 0.0318(8) 0.0430(8) -0.0057(6) 0.0149(6) -0.0001(6) C10 0.0309(7) 0.0259(7) 0.0368(8) -0.0025(6) 0.0125(5) -0.0041(6) C11 0.0299(7) 0.0246(7) 0.0349(7) -0.0010(5) 0.0152(5) -0.0030(6) C12 0.0397(8) 0.0267(7) 0.0380(8) -0.0001(6) 0.0202(6) -0.0042(6) C13 0.0532(9) 0.0336(8) 0.0375(8) -0.0019(6) 0.0232(7) -0.0083(8) C14 0.0490(9) 0.0356(9) 0.0330(8) 0.0037(6) 0.0102(7) -0.0058(7) C15 0.0332(7) 0.0300(8) 0.0414(8) 0.0003(6) 0.0073(6) -0.0042(7) C16 0.0435(8) 0.0355(9) 0.0559(10) 0.0031(7) 0.0330(8) 0.0007(7) C17 0.0348(8) 0.0394(9) 0.0639(11) 0.0095(8) 0.0257(8) 0.0048(7) C18 0.0334(8) 0.0390(9) 0.0444(9) 0.0103(7) 0.0144(6) 0.0017(7) C19 0.0330(7) 0.0337(8) 0.0373(8) 0.0019(6) 0.0158(6) -0.0022(6) _refine_ls_extinction_method None _oxford_refine_ls_scale 1.037(7) loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag O1 . C2 . 1.3507(18) yes O1 . C8 . 1.4617(17) yes C2 . O3 . 1.1975(17) yes C2 . N4 . 1.432(2) yes N4 . C5 . 1.5253(19) yes N4 . C6 . 1.452(2) yes C5 . C6 . 1.437(2) yes C5 . C8 . 1.516(2) yes C5 . H51 . 0.982 no C6 . C7 . 1.310(2) yes C7 . H71 . 0.950 no C7 . H72 . 0.981 no C8 . C9 . 1.523(2) yes C8 . H81 . 0.984 no C9 . C10 . 1.516(2) yes C9 . H91 . 1.002 no C9 . H92 . 0.962 no C10 . C11 . 1.434(2) yes C10 . C15 . 1.372(2) yes C11 . C12 . 1.434(2) yes C11 . C19 . 1.417(2) yes C12 . C13 . 1.418(2) yes C12 . C16 . 1.417(2) yes C13 . C14 . 1.356(2) yes C13 . H131 . 1.000 no C14 . C15 . 1.408(3) yes C14 . H141 . 0.995 no C15 . H151 . 0.953 no C16 . C17 . 1.357(2) yes C16 . H161 . 0.975 no C17 . C18 . 1.410(3) yes C17 . H171 . 0.984 no C18 . C19 . 1.368(2) yes C18 . H181 . 1.000 no C19 . H191 . 0.981 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 C2 . O1 . C8 . 111.63(11) yes O1 . C2 . O3 . 122.64(14) yes O1 . C2 . N4 . 112.66(12) yes O3 . C2 . N4 . 124.70(14) yes C2 . N4 . C5 . 104.27(11) yes C2 . N4 . C6 . 108.67(12) yes C5 . N4 . C6 . 57.66(10) yes N4 . C5 . C6 . 58.60(10) yes N4 . C5 . C8 . 106.87(11) yes C6 . C5 . C8 . 116.60(13) yes N4 . C5 . H51 . 116.7 no C6 . C5 . H51 . 122.7 no C8 . C5 . H51 . 118.3 no N4 . C6 . C5 . 63.74(11) yes N4 . C6 . C7 . 140.90(15) yes C5 . C6 . C7 . 154.99(16) yes C6 . C7 . H71 . 121.6 no C6 . C7 . H72 . 116.9 no H71 . C7 . H72 . 121.5 no C5 . C8 . O1 . 103.66(11) yes C5 . C8 . C9 . 115.04(13) yes O1 . C8 . C9 . 110.23(12) yes C5 . C8 . H81 . 110.2 no O1 . C8 . H81 . 108.0 no C9 . C8 . H81 . 109.4 no C8 . C9 . C10 . 112.07(12) yes C8 . C9 . H91 . 108.0 no C10 . C9 . H91 . 110.3 no C8 . C9 . H92 . 108.0 no C10 . C9 . H92 . 110.0 no H91 . C9 . H92 . 108.4 no C9 . C10 . C11 . 120.79(12) yes C9 . C10 . C15 . 120.00(13) yes C11 . C10 . C15 . 119.13(14) yes C10 . C11 . C12 . 118.59(12) yes C10 . C11 . C19 . 123.27(13) yes C12 . C11 . C19 . 118.13(12) yes C11 . C12 . C13 . 119.39(13) yes C11 . C12 . C16 . 118.59(13) yes C13 . C12 . C16 . 122.02(14) yes C12 . C13 . C14 . 120.65(14) yes C12 . C13 . H131 . 119.1 no C14 . C13 . H131 . 120.3 no C13 . C14 . C15 . 120.31(14) yes C13 . C14 . H141 . 120.3 no C15 . C14 . H141 . 119.4 no C14 . C15 . C10 . 121.88(15) yes C14 . C15 . H151 . 117.8 no C10 . C15 . H151 . 120.3 no C12 . C16 . C17 . 121.69(14) yes C12 . C16 . H161 . 118.8 no C17 . C16 . H161 . 119.5 no C16 . C17 . C18 . 119.87(15) yes C16 . C17 . H171 . 122.9 no C18 . C17 . H171 . 117.3 no C17 . C18 . C19 . 120.52(15) yes C17 . C18 . H181 . 120.6 no C19 . C18 . H181 . 118.9 no C11 . C19 . C18 . 121.19(14) yes C11 . C19 . H191 . 119.9 no C18 . C19 . H191 . 118.9 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 C5 . H51 . O3 4_464 127 0.98 2.53 3.220(2) yes C19 . H191 . O3 4_464 168 0.98 2.57 3.534(2) yes _chemical_name_common . #============================================================================== data_23 _database_code_depnum_ccdc_archive 'CCDC 767255' #TrackingRef 'Combined.cif' #============================================================================== _audit_creation_date 10-02-22 _audit_creation_method CRYSTALS_ver_12.86 _ccdc_journal_depnumber ? _oxford_structure_analysis_title '11081300 011ajt08' _chemical_name_systematic 1-96 _chemical_melting_point . _cell_length_a 8.3937(4) _cell_length_b 11.5174(7) _cell_length_c 13.4324(6) _cell_angle_alpha 90 _cell_angle_beta 100.112(3) _cell_angle_gamma 90 _cell_volume 1278.39(11) _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 1 21/a 1 ' _symmetry_space_group_name_Hall '-P 2yab' 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 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' _cell_formula_units_Z 4 # Given Formula = C12 H21 N1 O2 # Dc = 1.10 Fooo = 464.00 Mu = 0.74 M = 211.30 # Found Formula = C12 H21 N1 O2 # Dc = 1.10 FOOO = 464.00 Mu = 0.74 M = 211.30 _chemical_formula_sum 'C12 H21 N1 O2' _chemical_formula_moiety 'C12 H21 N1 O2' _chemical_compound_source . _chemical_formula_weight 211.30 _cell_measurement_reflns_used 2837 _cell_measurement_theta_min 5 _cell_measurement_theta_max 27 _cell_measurement_temperature 150 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_min 0.08 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_max 0.30 _exptl_crystal_density_diffrn 1.098 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 464 _exptl_absorpt_coefficient_mu 0.074 # Sheldrick geometric approximatio 0.99 0.99 _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 0.99 # 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 5022 _reflns_number_total 2863 _diffrn_reflns_av_R_equivalents 0.053 # Number of reflections with Friedels Law is 2863 # Number of reflections without Friedels Law is 5022 # Theoretical number of reflections is about 2952 _diffrn_reflns_theta_min 5.551 _diffrn_reflns_theta_max 27.550 _diffrn_measured_fraction_theta_max 0.971 _diffrn_reflns_theta_full 26.999 _diffrn_measured_fraction_theta_full 0.976 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _reflns_limit_h_min -10 _reflns_limit_h_max 10 _reflns_limit_k_min 0 _reflns_limit_k_max 14 _reflns_limit_l_min 0 _reflns_limit_l_max 17 _oxford_diffrn_Wilson_B_factor 3.42 _oxford_diffrn_Wilson_scale 0.42 _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 0.24 # 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 2862 _refine_ls_number_restraints 0 _refine_ls_number_parameters 136 _oxford_refine_ls_R_factor_ref 0.0763 _refine_ls_wR_factor_ref 0.1592 _refine_ls_goodness_of_fit_ref 1.0409 _refine_ls_shift/su_max 0.000315 # The values computed from all data _oxford_reflns_number_all 2863 _refine_ls_R_factor_all 0.0764 _refine_ls_wR_factor_all 0.1595 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 2076 _refine_ls_R_factor_gt 0.0528 _refine_ls_wR_factor_gt 0.1422 # 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^) + ( 0.10P)^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., 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 O1 O 0.11134(12) 0.87328(8) 0.09100(7) 0.0378 1.0000 Uani . . . . . . . C2 C 0.21499(17) 0.80607(13) 0.04911(10) 0.0356 1.0000 Uani . . . . . . . O3 O 0.17292(13) 0.71114(10) 0.01414(8) 0.0443 1.0000 Uani . . . . . . . N4 N 0.35626(15) 0.86108(10) 0.05352(9) 0.0374 1.0000 Uani . . . . . . . C5 C 0.36755(17) 0.96255(13) 0.11959(11) 0.0377 1.0000 Uani . . . . . . . C6 C 0.18567(17) 0.98717(13) 0.11241(11) 0.0368 1.0000 Uani . . . . . . . C7 C 0.12854(19) 1.04133(14) 0.20309(11) 0.0408 1.0000 Uani . . . . . . . C8 C -0.0549(2) 1.03487(17) 0.19178(12) 0.0492 1.0000 Uani . . . . . . . C9 C 0.1848(3) 1.16759(16) 0.21328(14) 0.0558 1.0000 Uani . . . . . . . C10 C 0.46210(18) 0.93865(14) 0.22544(11) 0.0414 1.0000 Uani . . . . . . . C11 C 0.43612(19) 0.82245(14) 0.27205(11) 0.0419 1.0000 Uani . . . . . . . C12 C 0.5049(2) 0.80877(17) 0.38370(12) 0.0539 1.0000 Uani . . . . . . . C13 C 0.4985(3) 0.6858(2) 0.42169(14) 0.0613 1.0000 Uani . . . . . . . C14 C 0.5635(5) 0.6726(3) 0.53378(17) 0.1032 1.0000 Uani . . . . . . . C15 C 0.5644(2) 1.01790(18) 0.26941(15) 0.0602 1.0000 Uani . . . . . . . H51 H 0.4139 1.0264 0.0900 0.0434 1.0000 Uiso R . . . . . . H61 H 0.1515 1.0364 0.0526 0.0420 1.0000 Uiso R . . . . . . H71 H 0.1782 0.9981 0.2652 0.0481 1.0000 Uiso R . . . . . . H81 H -0.0868 1.0700 0.2492 0.0709 1.0000 Uiso R . . . . . . H82 H -0.1029 1.0779 0.1326 0.0727 1.0000 Uiso R . . . . . . H83 H -0.0883 0.9547 0.1898 0.0709 1.0000 Uiso R . . . . . . H93 H 0.1577 1.1986 0.2746 0.0834 1.0000 Uiso R . . . . . . H92 H 0.1328 1.2124 0.1550 0.0817 1.0000 Uiso R . . . . . . H91 H 0.3013 1.1723 0.2161 0.0820 1.0000 Uiso R . . . . . . H111 H 0.3202 0.8073 0.2613 0.0496 1.0000 Uiso R . . . . . . H112 H 0.4846 0.7615 0.2326 0.0514 1.0000 Uiso R . . . . . . H121 H 0.6175 0.8312 0.3946 0.0652 1.0000 Uiso R . . . . . . H122 H 0.4507 0.8590 0.4233 0.0633 1.0000 Uiso R . . . . . . H131 H 0.5677 0.6346 0.3861 0.0733 1.0000 Uiso R . . . . . . H132 H 0.3868 0.6573 0.4077 0.0734 1.0000 Uiso R . . . . . . H143 H 0.5494 0.5928 0.5561 0.1510 1.0000 Uiso R . . . . . . H142 H 0.6796 0.6927 0.5450 0.1525 1.0000 Uiso R . . . . . . H141 H 0.5094 0.7276 0.5709 0.1520 1.0000 Uiso R . . . . . . H151 H 0.5766 1.0877 0.2338 0.0694 1.0000 Uiso R . . . . . . H152 H 0.6205 1.0072 0.3341 0.0703 1.0000 Uiso R . . . . . . H41 H 0.4413 0.8292 0.0323 0.0502 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 O1 0.0364(5) 0.0327(6) 0.0453(5) -0.0030(4) 0.0100(4) 0.0000(4) C2 0.0397(7) 0.0326(7) 0.0351(6) 0.0016(5) 0.0079(6) 0.0029(6) O3 0.0467(6) 0.0359(6) 0.0516(6) -0.0083(4) 0.0118(5) -0.0035(5) N4 0.0385(6) 0.0329(7) 0.0428(6) -0.0004(5) 0.0123(5) 0.0002(5) C5 0.0409(8) 0.0288(7) 0.0446(7) 0.0014(6) 0.0111(6) -0.0039(6) C6 0.0427(8) 0.0277(7) 0.0401(7) 0.0016(5) 0.0080(6) 0.0007(6) C7 0.0501(8) 0.0363(8) 0.0368(7) 0.0005(6) 0.0095(6) 0.0057(6) C8 0.0501(9) 0.0547(10) 0.0440(8) -0.0023(7) 0.0112(7) 0.0131(8) C9 0.0766(12) 0.0373(9) 0.0563(9) -0.0081(7) 0.0197(9) 0.0017(9) C10 0.0368(7) 0.0372(8) 0.0496(8) -0.0004(6) 0.0064(6) -0.0021(6) C11 0.0415(8) 0.0387(8) 0.0442(8) 0.0037(6) 0.0039(6) -0.0014(6) C12 0.0571(10) 0.0577(11) 0.0450(8) 0.0018(7) 0.0031(7) -0.0008(8) C13 0.0646(11) 0.0678(13) 0.0495(9) 0.0142(9) 0.0043(8) 0.0009(10) C14 0.145(3) 0.106(2) 0.0544(12) 0.0272(13) 0.0046(14) 0.010(2) C15 0.0545(10) 0.0507(11) 0.0692(11) 0.0020(8) -0.0061(8) -0.0143(8) _refine_ls_extinction_method None _oxford_refine_ls_scale 1.564(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 O1 . C2 . 1.3581(17) yes O1 . C6 . 1.4593(17) yes C2 . O3 . 1.2176(18) yes C2 . N4 . 1.3366(19) yes N4 . C5 . 1.4605(19) yes N4 . H41 . 0.893 no C5 . C6 . 1.539(2) yes C5 . C10 . 1.527(2) yes C5 . H51 . 0.951 no C6 . C7 . 1.519(2) yes C6 . H61 . 0.984 no C7 . C8 . 1.522(2) yes C7 . C9 . 1.528(2) yes C7 . H71 . 0.998 no C8 . H81 . 0.951 no C8 . H82 . 0.964 no C8 . H83 . 0.964 no C9 . H93 . 0.961 no C9 . H92 . 0.975 no C9 . H91 . 0.974 no C10 . C11 . 1.509(2) yes C10 . C15 . 1.319(2) yes C11 . C12 . 1.518(2) yes C11 . H111 . 0.974 no C11 . H112 . 1.007 no C12 . C13 . 1.510(3) yes C12 . H121 . 0.966 no C12 . H122 . 0.954 no C13 . C14 . 1.516(3) yes C13 . H131 . 1.005 no C13 . H132 . 0.981 no C14 . H143 . 0.980 no C14 . H142 . 0.987 no C14 . H141 . 0.967 no C15 . H151 . 0.950 no C15 . H152 . 0.921 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 C2 . O1 . C6 . 108.13(11) yes O1 . C2 . O3 . 120.54(13) yes O1 . C2 . N4 . 109.83(12) yes O3 . C2 . N4 . 129.62(13) yes C2 . N4 . C5 . 111.63(12) yes C2 . N4 . H41 . 123.0 no C5 . N4 . H41 . 123.6 no N4 . C5 . C6 . 98.72(11) yes N4 . C5 . C10 . 112.91(12) yes C6 . C5 . C10 . 116.06(11) yes N4 . C5 . H51 . 110.7 no C6 . C5 . H51 . 107.8 no C10 . C5 . H51 . 110.1 no C5 . C6 . O1 . 103.40(11) yes C5 . C6 . C7 . 118.34(12) yes O1 . C6 . C7 . 110.05(11) yes C5 . C6 . H61 . 107.5 no O1 . C6 . H61 . 107.7 no C7 . C6 . H61 . 109.3 no C6 . C7 . C8 . 110.86(12) yes C6 . C7 . C9 . 109.07(13) yes C8 . C7 . C9 . 110.28(14) yes C6 . C7 . H71 . 108.7 no C8 . C7 . H71 . 109.0 no C9 . C7 . H71 . 108.8 no C7 . C8 . H81 . 108.8 no C7 . C8 . H82 . 109.1 no H81 . C8 . H82 . 108.3 no C7 . C8 . H83 . 109.5 no H81 . C8 . H83 . 108.0 no H82 . C8 . H83 . 113.1 no C7 . C9 . H93 . 108.4 no C7 . C9 . H92 . 110.2 no H93 . C9 . H92 . 110.6 no C7 . C9 . H91 . 110.4 no H93 . C9 . H91 . 109.4 no H92 . C9 . H91 . 107.8 no C5 . C10 . C11 . 117.18(12) yes C5 . C10 . C15 . 118.89(15) yes C11 . C10 . C15 . 123.90(15) yes C10 . C11 . C12 . 116.38(14) yes C10 . C11 . H111 . 108.1 no C12 . C11 . H111 . 108.9 no C10 . C11 . H112 . 107.4 no C12 . C11 . H112 . 109.2 no H111 . C11 . H112 . 106.4 no C11 . C12 . C13 . 113.68(15) yes C11 . C12 . H121 . 108.3 no C13 . C12 . H121 . 106.9 no C11 . C12 . H122 . 110.6 no C13 . C12 . H122 . 109.4 no H121 . C12 . H122 . 107.7 no C12 . C13 . C14 . 113.7(2) yes C12 . C13 . H131 . 109.4 no C14 . C13 . H131 . 106.0 no C12 . C13 . H132 . 109.8 no C14 . C13 . H132 . 108.8 no H131 . C13 . H132 . 109.0 no C13 . C14 . H143 . 110.9 no C13 . C14 . H142 . 107.5 no H143 . C14 . H142 . 110.0 no C13 . C14 . H141 . 109.1 no H143 . C14 . H141 . 111.3 no H142 . C14 . H141 . 108.0 no C10 . C15 . H151 . 118.7 no C10 . C15 . H152 . 120.9 no H151 . C15 . H152 . 120.4 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 C5 . H51 . O3 3_555 140 0.95 2.58 3.365(3) yes N4 . H41 . O3 4_565 163 0.89 2.05 2.921(3) yes _chemical_name_common 1-96