# Supplementary Material (ESI) for Organic and Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2010 data_global _journal_coden_Cambridge 177 loop_ _publ_author_name 'Peter Rutledge' 'Vicky J. Dungan' 'Helge Mueller-Bunz' 'Yannick Ortin' _publ_contact_author_name 'Peter Rutledge' _publ_contact_author_email P.RUTLEDGE@CHEM.USYD.EDU.AU _publ_section_title ; Design and synthesis of a non-heme iron(II) oxidase mimic for alkene dihydroxylation ; # Attachment 'Dungan_Bromide_13.cif' data_rut13 _database_code_depnum_ccdc_archive 'CCDC 752132' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C25 H23 N2 O4 Br' _chemical_formula_weight 495.36 _chemical_absolute_configuration ad loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' _cell_length_a 10.0994(11) _cell_length_b 10.1912(11) _cell_length_c 11.6410(12) _cell_angle_alpha 91.432(2) _cell_angle_beta 94.023(2) _cell_angle_gamma 95.126(2) _cell_volume 1189.8(2) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 6169 _cell_measurement_theta_min 0.00 _cell_measurement_theta_max 0.00 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 1.00 _exptl_crystal_size_mid 1.00 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.383 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 508 _exptl_absorpt_coefficient_mu 1.760 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.3151 _exptl_absorpt_correction_T_max 0.9172 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean 8.366 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15455 _diffrn_reflns_av_R_equivalents 0.0312 _diffrn_reflns_av_sigmaI/netI 0.0648 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.75 _diffrn_reflns_theta_max 24.00 _reflns_number_total 7380 _reflns_number_gt 6163 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0399P)^2^+0.2420P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.008(8) _refine_ls_number_reflns 7380 _refine_ls_number_parameters 579 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0528 _refine_ls_R_factor_gt 0.0425 _refine_ls_wR_factor_ref 0.1127 _refine_ls_wR_factor_gt 0.1066 _refine_ls_goodness_of_fit_ref 1.034 _refine_ls_restrained_S_all 1.034 _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Br1 Br 0.09479(5) -0.18938(5) 0.72256(5) 0.0923(2) Uani 1 1 d . . . C1 C 0.2783(6) -0.1314(6) 0.7785(6) 0.0983(19) Uani 1 1 d . . . H1A H 0.2817 -0.1112 0.8606 0.118 Uiso 1 1 calc R . . H1B H 0.3344 -0.2023 0.7666 0.118 Uiso 1 1 calc R . . C2 C 0.3309(5) -0.0130(5) 0.7182(4) 0.0727(13) Uani 1 1 d . . . N1 N 0.2994(3) 0.1021(4) 0.7593(3) 0.0589(8) Uani 1 1 d . . . C3 C 0.4086(5) -0.0215(6) 0.6250(5) 0.0832(15) Uani 1 1 d . . . H3 H 0.4292 -0.1031 0.5975 0.100 Uiso 1 1 calc R . . C4 C 0.4550(6) 0.0924(7) 0.5736(5) 0.0923(17) Uani 1 1 d . . . H4 H 0.5064 0.0889 0.5106 0.111 Uiso 1 1 calc R . . C5 C 0.4242(5) 0.2080(5) 0.6164(4) 0.0722(13) Uani 1 1 d . . . H5 H 0.4549 0.2863 0.5837 0.087 Uiso 1 1 calc R . . C6 C 0.3455(4) 0.2104(5) 0.7105(4) 0.0590(10) Uani 1 1 d . . . C7 C 0.3149(5) 0.3389(5) 0.7628(5) 0.0711(13) Uani 1 1 d . . . H7A H 0.3006 0.3991 0.7008 0.085 Uiso 1 1 calc R . . H7B H 0.3931 0.3752 0.8101 0.085 Uiso 1 1 calc R . . C8 C 0.1958(5) 0.3365(5) 0.8359(4) 0.0648(12) Uani 1 1 d . . . C9 C 0.1754(6) 0.4787(5) 0.8753(6) 0.0995(19) Uani 1 1 d . . . H9A H 0.1674 0.5327 0.8092 0.149 Uiso 1 1 calc R . . H9B H 0.2504 0.5136 0.9255 0.149 Uiso 1 1 calc R . . H9C H 0.0957 0.4783 0.9156 0.149 Uiso 1 1 calc R . . C10 C 0.2160(5) 0.2514(6) 0.9403(4) 0.0743(14) Uani 1 1 d . . . O1 O 0.3087(4) 0.2632(5) 1.0100(3) 0.1100(15) Uani 1 1 d . . . O2 O 0.1109(3) 0.1654(4) 0.9495(2) 0.0690(9) Uani 1 1 d . . . C11 C 0.0189(4) 0.1606(4) 0.8503(3) 0.0553(10) Uani 1 1 d . . . H11 H 0.0199 0.0764 0.8080 0.066 Uiso 1 1 calc R . . C12 C -0.1189(4) 0.1759(5) 0.8865(4) 0.0624(11) Uani 1 1 d . . . C13 C -0.1496(6) 0.2845(6) 0.9496(6) 0.0938(18) Uani 1 1 d . . . H13 H -0.0827 0.3508 0.9716 0.113 Uiso 1 1 calc R . . C14 C -0.2771(8) 0.2966(9) 0.9805(7) 0.114(2) Uani 1 1 d . . . H14 H -0.2959 0.3699 1.0236 0.137 Uiso 1 1 calc R . . C15 C -0.3732(7) 0.2025(12) 0.9481(8) 0.119(3) Uani 1 1 d . . . H15 H -0.4596 0.2115 0.9678 0.143 Uiso 1 1 calc R . . C16 C -0.3481(7) 0.0953(11) 0.8878(6) 0.122(3) Uani 1 1 d . . . H16 H -0.4164 0.0301 0.8666 0.146 Uiso 1 1 calc R . . C17 C -0.2176(6) 0.0814(8) 0.8565(5) 0.0943(18) Uani 1 1 d . . . H17 H -0.1998 0.0067 0.8149 0.113 Uiso 1 1 calc R . . N2 N 0.0725(3) 0.2678(3) 0.7820(3) 0.0525(8) Uani 1 1 d . . . C18 C 0.0244(5) 0.2881(5) 0.6723(4) 0.0573(11) Uani 1 1 d . . . O3 O 0.0624(4) 0.3784(3) 0.6145(3) 0.0764(9) Uani 1 1 d . . . O4 O -0.0723(3) 0.1931(3) 0.6388(2) 0.0658(8) Uani 1 1 d . . . C19 C -0.1345(5) 0.2029(6) 0.5233(4) 0.0736(13) Uani 1 1 d . . . H19A H -0.1526 0.2935 0.5110 0.088 Uiso 1 1 calc R . . H19B H -0.2190 0.1490 0.5167 0.088 Uiso 1 1 calc R . . C20 C -0.0503(4) 0.1598(5) 0.4325(3) 0.0596(11) Uani 1 1 d . . . C21 C 0.0653(6) 0.1012(5) 0.4529(4) 0.0802(14) Uani 1 1 d . . . H21 H 0.0955 0.0860 0.5283 0.096 Uiso 1 1 calc R . . C22 C 0.1378(7) 0.0642(6) 0.3636(5) 0.0955(18) Uani 1 1 d . . . H22 H 0.2174 0.0267 0.3800 0.115 Uiso 1 1 calc R . . C23 C 0.0961(7) 0.0812(7) 0.2532(5) 0.103(2) Uani 1 1 d . . . H23 H 0.1437 0.0519 0.1935 0.124 Uiso 1 1 calc R . . C24 C -0.0156(9) 0.1412(11) 0.2307(5) 0.147(4) Uani 1 1 d . . . H24 H -0.0436 0.1574 0.1550 0.176 Uiso 1 1 calc R . . C25 C -0.0889(7) 0.1788(8) 0.3194(5) 0.118(3) Uani 1 1 d . . . H25 H -0.1671 0.2183 0.3019 0.141 Uiso 1 1 calc R . . Br2 Br 0.56907(6) 0.33402(6) 0.33716(5) 0.1017(2) Uani 1 1 d . . . C26 C 0.3930(6) 0.3616(5) 0.2665(5) 0.0859(16) Uani 1 1 d . . . H26A H 0.3985 0.3743 0.1846 0.103 Uiso 1 1 calc R . . H26B H 0.3320 0.2842 0.2761 0.103 Uiso 1 1 calc R . . C27 C 0.3415(4) 0.4792(4) 0.3207(4) 0.0565(10) Uani 1 1 d . . . N3 N 0.3817(3) 0.5960(3) 0.2775(3) 0.0517(8) Uani 1 1 d . . . C28 C 0.2584(5) 0.4694(5) 0.4095(4) 0.0729(13) Uani 1 1 d . . . H28 H 0.2310 0.3874 0.4375 0.087 Uiso 1 1 calc R . . C29 C 0.2168(6) 0.5811(5) 0.4558(5) 0.0822(15) Uani 1 1 d . . . H29 H 0.1605 0.5762 0.5158 0.099 Uiso 1 1 calc R . . C30 C 0.2576(5) 0.6989(5) 0.4142(4) 0.0723(13) Uani 1 1 d . . . H30 H 0.2308 0.7760 0.4460 0.087 Uiso 1 1 calc R . . C31 C 0.3400(4) 0.7043(4) 0.3235(3) 0.0505(9) Uani 1 1 d . . . C32 C 0.3822(4) 0.8320(5) 0.2708(4) 0.0584(11) Uani 1 1 d . . . H32A H 0.4022 0.8980 0.3325 0.070 Uiso 1 1 calc R . . H32B H 0.3067 0.8583 0.2235 0.070 Uiso 1 1 calc R . . C33 C 0.5017(4) 0.8362(4) 0.1968(4) 0.0529(10) Uani 1 1 d . . . C34 C 0.5338(6) 0.9790(5) 0.1579(6) 0.0847(16) Uani 1 1 d . . . H34A H 0.5622 1.0354 0.2240 0.127 Uiso 1 1 calc R . . H34B H 0.4555 1.0094 0.1196 0.127 Uiso 1 1 calc R . . H34C H 0.6036 0.9808 0.1059 0.127 Uiso 1 1 calc R . . C35 C 0.4756(4) 0.7452(5) 0.0922(4) 0.0593(11) Uani 1 1 d . . . O5 O 0.3885(3) 0.7487(4) 0.0179(3) 0.0858(10) Uani 1 1 d . . . O6 O 0.5701(3) 0.6620(3) 0.0861(2) 0.0581(7) Uani 1 1 d . . . C36 C 0.6604(4) 0.6711(4) 0.1881(3) 0.0530(9) Uani 1 1 d . . . H36 H 0.6453 0.5914 0.2324 0.064 Uiso 1 1 calc R . . C37 C 0.8013(4) 0.6833(5) 0.1532(4) 0.0618(11) Uani 1 1 d . . . C38 C 0.8870(5) 0.5930(7) 0.1866(5) 0.0880(16) Uani 1 1 d . . . H38 H 0.8589 0.5241 0.2327 0.106 Uiso 1 1 calc R . . C39 C 1.0169(7) 0.6038(10) 0.1516(7) 0.114(2) Uani 1 1 d . . . H39 H 1.0756 0.5430 0.1756 0.137 Uiso 1 1 calc R . . C40 C 1.0566(7) 0.7004(11) 0.0844(8) 0.122(3) Uani 1 1 d . . . H40 H 1.1423 0.7051 0.0594 0.147 Uiso 1 1 calc R . . C41 C 0.9767(9) 0.7897(9) 0.0527(8) 0.128(3) Uani 1 1 d . . . H41 H 1.0071 0.8590 0.0082 0.154 Uiso 1 1 calc R . . C42 C 0.8467(6) 0.7808(7) 0.0854(6) 0.0950(18) Uani 1 1 d . . . H42 H 0.7899 0.8428 0.0603 0.114 Uiso 1 1 calc R . . N4 N 0.6203(3) 0.7833(3) 0.2521(3) 0.0511(8) Uani 1 1 d . . . C43 C 0.6694(4) 0.8194(5) 0.3605(4) 0.0560(11) Uani 1 1 d . . . O7 O 0.6365(4) 0.9100(4) 0.4170(3) 0.0747(9) Uani 1 1 d . . . O8 O 0.7619(3) 0.7392(4) 0.3950(3) 0.0728(9) Uani 1 1 d . . . C44 C 0.8333(5) 0.7710(6) 0.5040(4) 0.0803(14) Uani 1 1 d . . . H44A H 0.8377 0.8654 0.5189 0.096 Uiso 1 1 calc R . . H44B H 0.9237 0.7467 0.5013 0.096 Uiso 1 1 calc R . . C45 C 0.7688(5) 0.7012(5) 0.6010(4) 0.0716(13) Uani 1 1 d . . . C46 C 0.6917(7) 0.7653(7) 0.6700(6) 0.0997(18) Uani 1 1 d . . . H46 H 0.6747 0.8518 0.6556 0.120 Uiso 1 1 calc R . . C47 C 0.6370(8) 0.7002(10) 0.7642(6) 0.126(3) Uani 1 1 d . . . H47 H 0.5842 0.7441 0.8118 0.151 Uiso 1 1 calc R . . C48 C 0.6610(10) 0.5764(11) 0.7848(8) 0.135(3) Uani 1 1 d . . . H48 H 0.6229 0.5327 0.8453 0.162 Uiso 1 1 calc R . . C49 C 0.7433(11) 0.5129(9) 0.7154(9) 0.140(3) Uani 1 1 d . . . H49 H 0.7616 0.4266 0.7293 0.168 Uiso 1 1 calc R . . C50 C 0.7982(9) 0.5798(7) 0.6248(7) 0.121(2) Uani 1 1 d . . . H50 H 0.8564 0.5389 0.5802 0.145 Uiso 1 1 calc 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 Br1 0.1009(4) 0.0797(4) 0.0920(4) 0.0020(3) -0.0092(3) -0.0024(3) C1 0.110(4) 0.082(4) 0.100(4) 0.014(3) -0.029(4) 0.020(3) C2 0.066(3) 0.081(3) 0.070(3) -0.009(3) -0.016(2) 0.021(2) N1 0.059(2) 0.068(2) 0.0497(19) -0.0023(17) 0.0023(16) 0.0077(18) C3 0.080(3) 0.088(4) 0.082(4) -0.026(3) -0.004(3) 0.031(3) C4 0.081(4) 0.124(5) 0.076(4) -0.021(4) 0.020(3) 0.028(4) C5 0.067(3) 0.091(4) 0.062(3) -0.002(3) 0.019(2) 0.011(2) C6 0.053(2) 0.075(3) 0.050(2) -0.008(2) 0.0077(19) 0.010(2) C7 0.064(3) 0.074(3) 0.075(3) -0.014(3) 0.021(2) -0.004(2) C8 0.061(3) 0.074(3) 0.060(3) -0.011(2) 0.021(2) 0.001(2) C9 0.093(4) 0.077(3) 0.128(5) -0.046(3) 0.031(4) -0.003(3) C10 0.060(3) 0.114(4) 0.048(3) -0.021(3) 0.008(2) 0.008(3) O1 0.074(2) 0.189(5) 0.063(2) -0.032(3) -0.008(2) 0.008(3) O2 0.0562(18) 0.111(3) 0.0410(16) 0.0105(16) 0.0042(13) 0.0126(17) C11 0.055(2) 0.067(3) 0.045(2) 0.0109(19) 0.0075(18) 0.0078(19) C12 0.057(3) 0.081(3) 0.049(2) 0.022(2) 0.007(2) 0.001(2) C13 0.084(4) 0.093(4) 0.113(5) 0.014(4) 0.050(4) 0.019(3) C14 0.091(5) 0.133(6) 0.131(6) 0.042(5) 0.058(4) 0.036(5) C15 0.071(4) 0.196(9) 0.106(5) 0.082(6) 0.042(4) 0.047(5) C16 0.060(4) 0.211(10) 0.086(5) 0.023(5) 0.004(3) -0.026(5) C17 0.076(4) 0.150(6) 0.053(3) -0.001(3) 0.009(2) -0.009(4) N2 0.0481(18) 0.064(2) 0.0462(19) 0.0034(16) 0.0128(15) 0.0038(16) C18 0.064(3) 0.063(3) 0.050(3) 0.009(2) 0.023(2) 0.017(2) O3 0.096(2) 0.072(2) 0.067(2) 0.0248(17) 0.0302(18) 0.0107(18) O4 0.0704(19) 0.085(2) 0.0414(15) 0.0075(14) 0.0099(14) -0.0009(17) C19 0.063(3) 0.109(4) 0.049(3) 0.004(2) -0.006(2) 0.015(3) C20 0.064(3) 0.076(3) 0.041(2) 0.0076(19) 0.0086(19) 0.012(2) C21 0.094(4) 0.097(4) 0.055(3) 0.009(3) 0.003(3) 0.037(3) C22 0.109(4) 0.097(4) 0.090(4) -0.002(3) 0.016(3) 0.052(3) C23 0.118(5) 0.131(5) 0.069(4) -0.005(3) 0.032(3) 0.040(4) C24 0.155(7) 0.260(10) 0.040(3) 0.014(4) 0.008(4) 0.101(7) C25 0.104(4) 0.203(8) 0.057(3) 0.013(4) 0.001(3) 0.076(5) Br2 0.1077(4) 0.0915(4) 0.1169(5) 0.0261(3) 0.0331(4) 0.0444(3) C26 0.127(5) 0.060(3) 0.069(3) -0.002(2) 0.016(3) -0.006(3) C27 0.054(2) 0.061(3) 0.053(2) 0.003(2) 0.0031(19) 0.0011(19) N3 0.0478(17) 0.062(2) 0.0460(18) 0.0039(16) 0.0070(14) 0.0042(15) C28 0.078(3) 0.072(3) 0.070(3) 0.021(2) 0.016(3) 0.002(2) C29 0.087(3) 0.085(4) 0.082(3) 0.027(3) 0.047(3) 0.014(3) C30 0.073(3) 0.080(3) 0.070(3) 0.011(2) 0.029(2) 0.021(2) C31 0.043(2) 0.062(2) 0.049(2) 0.0076(19) 0.0103(17) 0.0123(18) C32 0.051(2) 0.067(3) 0.062(3) 0.012(2) 0.014(2) 0.019(2) C33 0.053(2) 0.052(2) 0.057(2) 0.0145(19) 0.0184(19) 0.0094(19) C34 0.090(4) 0.066(3) 0.103(4) 0.027(3) 0.029(3) 0.009(3) C35 0.052(2) 0.079(3) 0.047(2) 0.012(2) 0.009(2) 0.005(2) O5 0.067(2) 0.136(3) 0.0553(19) 0.0166(19) -0.0009(18) 0.017(2) O6 0.0529(16) 0.0752(19) 0.0460(15) -0.0054(13) 0.0065(12) 0.0046(14) C36 0.047(2) 0.064(2) 0.049(2) -0.0033(19) 0.0041(18) 0.0077(18) C37 0.056(2) 0.074(3) 0.056(3) -0.016(2) 0.011(2) 0.012(2) C38 0.069(3) 0.118(4) 0.081(4) -0.014(3) 0.008(3) 0.033(3) C39 0.073(4) 0.170(7) 0.104(5) -0.031(5) 0.003(4) 0.052(5) C40 0.063(4) 0.176(8) 0.122(6) -0.081(6) 0.034(4) -0.013(5) C41 0.100(5) 0.138(7) 0.148(7) -0.030(6) 0.073(5) -0.021(5) C42 0.069(3) 0.104(4) 0.117(5) 0.006(4) 0.045(3) 0.005(3) N4 0.0491(18) 0.062(2) 0.0429(19) -0.0015(15) 0.0098(15) 0.0061(15) C43 0.051(2) 0.064(3) 0.053(3) -0.005(2) 0.013(2) 0.004(2) O7 0.087(2) 0.074(2) 0.064(2) -0.0213(17) 0.0149(17) 0.0137(18) O8 0.0720(19) 0.099(2) 0.0493(17) -0.0104(16) -0.0011(15) 0.0278(18) C44 0.058(3) 0.115(4) 0.065(3) -0.007(3) -0.010(2) 0.007(3) C45 0.081(3) 0.087(3) 0.048(2) -0.013(2) -0.013(2) 0.028(3) C46 0.110(4) 0.110(4) 0.084(4) 0.004(3) 0.011(4) 0.037(4) C47 0.136(6) 0.180(8) 0.075(4) 0.015(5) 0.031(4) 0.066(6) C48 0.132(6) 0.161(8) 0.113(6) 0.051(6) 0.013(5) 0.006(6) C49 0.169(8) 0.121(6) 0.137(7) 0.027(5) 0.023(7) 0.034(6) C50 0.154(7) 0.103(5) 0.115(5) 0.003(4) 0.036(5) 0.040(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Br1 C1 1.956(6) . ? C1 C2 1.487(8) . ? C1 H1A 0.9700 . ? C1 H1B 0.9700 . ? C2 N1 1.330(6) . ? C2 C3 1.388(8) . ? N1 C6 1.316(6) . ? C3 C4 1.378(9) . ? C3 H3 0.9300 . ? C4 C5 1.338(8) . ? C4 H4 0.9300 . ? C5 C6 1.399(6) . ? C5 H5 0.9300 . ? C6 C7 1.496(7) . ? C7 C8 1.520(7) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 N2 1.466(6) . ? C8 C10 1.523(8) . ? C8 C9 1.545(7) . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C10 O1 1.190(6) . ? C10 O2 1.327(6) . ? O2 C11 1.427(5) . ? C11 N2 1.454(5) . ? C11 C12 1.502(6) . ? C11 H11 0.9800 . ? C12 C17 1.344(8) . ? C12 C13 1.383(8) . ? C13 C14 1.376(9) . ? C13 H13 0.9300 . ? C14 C15 1.329(12) . ? C14 H14 0.9300 . ? C15 C16 1.337(12) . ? C15 H15 0.9300 . ? C16 C17 1.410(10) . ? C16 H16 0.9300 . ? C17 H17 0.9300 . ? N2 C18 1.362(6) . ? C18 O3 1.204(5) . ? C18 O4 1.342(6) . ? O4 C19 1.453(5) . ? C19 C20 1.484(7) . ? C19 H19A 0.9700 . ? C19 H19B 0.9700 . ? C20 C21 1.367(7) . ? C20 C25 1.371(7) . ? C21 C22 1.377(8) . ? C21 H21 0.9300 . ? C22 C23 1.344(9) . ? C22 H22 0.9300 . ? C23 C24 1.344(10) . ? C23 H23 0.9300 . ? C24 C25 1.378(9) . ? C24 H24 0.9300 . ? C25 H25 0.9300 . ? Br2 C26 1.953(6) . ? C26 C27 1.492(7) . ? C26 H26A 0.9700 . ? C26 H26B 0.9700 . ? C27 N3 1.344(5) . ? C27 C28 1.377(6) . ? N3 C31 1.329(5) . ? C28 C29 1.361(7) . ? C28 H28 0.9300 . ? C29 C30 1.347(7) . ? C29 H29 0.9300 . ? C30 C31 1.389(6) . ? C30 H30 0.9300 . ? C31 C32 1.494(6) . ? C32 C33 1.529(6) . ? C32 H32A 0.9700 . ? C32 H32B 0.9700 . ? C33 N4 1.471(5) . ? C33 C35 1.506(7) . ? C33 C34 1.549(6) . ? C34 H34A 0.9600 . ? C34 H34B 0.9600 . ? C34 H34C 0.9600 . ? C35 O5 1.193(5) . ? C35 O6 1.337(5) . ? O6 C36 1.441(5) . ? C36 N4 1.453(5) . ? C36 C37 1.502(6) . ? C36 H36 0.9800 . ? C37 C42 1.352(8) . ? C37 C38 1.364(7) . ? C38 C39 1.396(10) . ? C38 H38 0.9300 . ? C39 C40 1.325(12) . ? C39 H39 0.9300 . ? C40 C41 1.312(13) . ? C40 H40 0.9300 . ? C41 C42 1.388(9) . ? C41 H41 0.9300 . ? C42 H42 0.9300 . ? N4 C43 1.352(5) . ? C43 O7 1.204(5) . ? C43 O8 1.342(6) . ? O8 C44 1.430(6) . ? C44 C45 1.504(8) . ? C44 H44A 0.9700 . ? C44 H44B 0.9700 . ? C45 C50 1.330(9) . ? C45 C46 1.353(8) . ? C46 C47 1.415(10) . ? C46 H46 0.9300 . ? C47 C48 1.330(12) . ? C47 H47 0.9300 . ? C48 C49 1.389(13) . ? C48 H48 0.9300 . ? C49 C50 1.390(11) . ? C49 H49 0.9300 . ? C50 H50 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 Br1 111.6(3) . . ? C2 C1 H1A 109.3 . . ? Br1 C1 H1A 109.3 . . ? C2 C1 H1B 109.3 . . ? Br1 C1 H1B 109.3 . . ? H1A C1 H1B 108.0 . . ? N1 C2 C3 121.8(5) . . ? N1 C2 C1 115.9(5) . . ? C3 C2 C1 122.3(5) . . ? C6 N1 C2 118.4(4) . . ? C4 C3 C2 119.3(5) . . ? C4 C3 H3 120.3 . . ? C2 C3 H3 120.3 . . ? C5 C4 C3 118.5(5) . . ? C5 C4 H4 120.7 . . ? C3 C4 H4 120.7 . . ? C4 C5 C6 119.6(5) . . ? C4 C5 H5 120.2 . . ? C6 C5 H5 120.2 . . ? N1 C6 C5 122.3(4) . . ? N1 C6 C7 117.2(4) . . ? C5 C6 C7 120.4(5) . . ? C6 C7 C8 117.2(4) . . ? C6 C7 H7A 108.0 . . ? C8 C7 H7A 108.0 . . ? C6 C7 H7B 108.0 . . ? C8 C7 H7B 108.0 . . ? H7A C7 H7B 107.2 . . ? N2 C8 C7 114.9(4) . . ? N2 C8 C10 99.5(4) . . ? C7 C8 C10 110.9(4) . . ? N2 C8 C9 111.7(4) . . ? C7 C8 C9 109.4(4) . . ? C10 C8 C9 110.1(4) . . ? C8 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C8 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? O1 C10 O2 122.9(5) . . ? O1 C10 C8 126.0(5) . . ? O2 C10 C8 111.0(4) . . ? C10 O2 C11 112.5(3) . . ? O2 C11 N2 103.3(3) . . ? O2 C11 C12 109.8(3) . . ? N2 C11 C12 114.1(3) . . ? O2 C11 H11 109.8 . . ? N2 C11 H11 109.8 . . ? C12 C11 H11 109.8 . . ? C17 C12 C13 117.9(5) . . ? C17 C12 C11 119.4(5) . . ? C13 C12 C11 122.7(5) . . ? C14 C13 C12 121.5(7) . . ? C14 C13 H13 119.3 . . ? C12 C13 H13 119.3 . . ? C15 C14 C13 119.3(8) . . ? C15 C14 H14 120.3 . . ? C13 C14 H14 120.3 . . ? C14 C15 C16 121.4(6) . . ? C14 C15 H15 119.3 . . ? C16 C15 H15 119.3 . . ? C15 C16 C17 119.7(7) . . ? C15 C16 H16 120.1 . . ? C17 C16 H16 120.1 . . ? C12 C17 C16 120.2(7) . . ? C12 C17 H17 119.9 . . ? C16 C17 H17 119.9 . . ? C18 N2 C11 122.9(4) . . ? C18 N2 C8 123.5(4) . . ? C11 N2 C8 112.8(3) . . ? O3 C18 O4 125.2(4) . . ? O3 C18 N2 125.0(5) . . ? O4 C18 N2 109.8(4) . . ? C18 O4 C19 116.0(4) . . ? O4 C19 C20 112.7(4) . . ? O4 C19 H19A 109.0 . . ? C20 C19 H19A 109.0 . . ? O4 C19 H19B 109.0 . . ? C20 C19 H19B 109.0 . . ? H19A C19 H19B 107.8 . . ? C21 C20 C25 116.4(4) . . ? C21 C20 C19 124.7(4) . . ? C25 C20 C19 119.0(4) . . ? C20 C21 C22 121.0(5) . . ? C20 C21 H21 119.5 . . ? C22 C21 H21 119.5 . . ? C23 C22 C21 121.4(5) . . ? C23 C22 H22 119.3 . . ? C21 C22 H22 119.3 . . ? C22 C23 C24 118.7(5) . . ? C22 C23 H23 120.6 . . ? C24 C23 H23 120.6 . . ? C23 C24 C25 120.3(6) . . ? C23 C24 H24 119.9 . . ? C25 C24 H24 119.9 . . ? C20 C25 C24 122.1(5) . . ? C20 C25 H25 119.0 . . ? C24 C25 H25 119.0 . . ? C27 C26 Br2 110.4(3) . . ? C27 C26 H26A 109.6 . . ? Br2 C26 H26A 109.6 . . ? C27 C26 H26B 109.6 . . ? Br2 C26 H26B 109.6 . . ? H26A C26 H26B 108.1 . . ? N3 C27 C28 121.9(4) . . ? N3 C27 C26 115.7(4) . . ? C28 C27 C26 122.3(4) . . ? C31 N3 C27 118.3(3) . . ? C29 C28 C27 119.1(4) . . ? C29 C28 H28 120.4 . . ? C27 C28 H28 120.4 . . ? C30 C29 C28 119.5(4) . . ? C30 C29 H29 120.2 . . ? C28 C29 H29 120.2 . . ? C29 C30 C31 119.5(5) . . ? C29 C30 H30 120.3 . . ? C31 C30 H30 120.3 . . ? N3 C31 C30 121.7(4) . . ? N3 C31 C32 117.0(3) . . ? C30 C31 C32 121.3(4) . . ? C31 C32 C33 117.7(4) . . ? C31 C32 H32A 107.9 . . ? C33 C32 H32A 107.9 . . ? C31 C32 H32B 107.9 . . ? C33 C32 H32B 107.9 . . ? H32A C32 H32B 107.2 . . ? N4 C33 C35 100.5(3) . . ? N4 C33 C32 114.4(3) . . ? C35 C33 C32 111.9(4) . . ? N4 C33 C34 111.5(4) . . ? C35 C33 C34 109.2(4) . . ? C32 C33 C34 109.1(4) . . ? C33 C34 H34A 109.5 . . ? C33 C34 H34B 109.5 . . ? H34A C34 H34B 109.5 . . ? C33 C34 H34C 109.5 . . ? H34A C34 H34C 109.5 . . ? H34B C34 H34C 109.5 . . ? O5 C35 O6 121.9(4) . . ? O5 C35 C33 126.6(4) . . ? O6 C35 C33 111.4(4) . . ? C35 O6 C36 111.9(3) . . ? O6 C36 N4 103.3(3) . . ? O6 C36 C37 109.2(3) . . ? N4 C36 C37 115.9(3) . . ? O6 C36 H36 109.4 . . ? N4 C36 H36 109.4 . . ? C37 C36 H36 109.4 . . ? C42 C37 C38 117.7(5) . . ? C42 C37 C36 121.7(4) . . ? C38 C37 C36 120.6(5) . . ? C37 C38 C39 120.0(7) . . ? C37 C38 H38 120.0 . . ? C39 C38 H38 120.0 . . ? C40 C39 C38 120.2(7) . . ? C40 C39 H39 119.9 . . ? C38 C39 H39 119.9 . . ? C41 C40 C39 120.9(7) . . ? C41 C40 H40 119.6 . . ? C39 C40 H40 119.6 . . ? C40 C41 C42 120.2(8) . . ? C40 C41 H41 119.9 . . ? C42 C41 H41 119.9 . . ? C37 C42 C41 121.0(7) . . ? C37 C42 H42 119.5 . . ? C41 C42 H42 119.5 . . ? C43 N4 C36 123.7(3) . . ? C43 N4 C33 122.7(3) . . ? C36 N4 C33 112.4(3) . . ? O7 C43 O8 125.2(4) . . ? O7 C43 N4 125.5(4) . . ? O8 C43 N4 109.3(4) . . ? C43 O8 C44 116.7(4) . . ? O8 C44 C45 112.2(4) . . ? O8 C44 H44A 109.2 . . ? C45 C44 H44A 109.2 . . ? O8 C44 H44B 109.2 . . ? C45 C44 H44B 109.2 . . ? H44A C44 H44B 107.9 . . ? C50 C45 C46 120.0(6) . . ? C50 C45 C44 119.2(5) . . ? C46 C45 C44 120.5(5) . . ? C45 C46 C47 119.7(6) . . ? C45 C46 H46 120.1 . . ? C47 C46 H46 120.1 . . ? C48 C47 C46 120.2(7) . . ? C48 C47 H47 119.9 . . ? C46 C47 H47 119.9 . . ? C47 C48 C49 119.5(8) . . ? C47 C48 H48 120.2 . . ? C49 C48 H48 120.2 . . ? C48 C49 C50 119.2(8) . . ? C48 C49 H49 120.4 . . ? C50 C49 H49 120.4 . . ? C45 C50 C49 121.1(7) . . ? C45 C50 H50 119.4 . . ? C49 C50 H50 119.4 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag Br1 C1 C2 N1 83.3(5) . . . . ? Br1 C1 C2 C3 -97.0(5) . . . . ? C3 C2 N1 C6 -1.0(6) . . . . ? C1 C2 N1 C6 178.7(4) . . . . ? N1 C2 C3 C4 0.2(8) . . . . ? C1 C2 C3 C4 -179.5(5) . . . . ? C2 C3 C4 C5 0.6(8) . . . . ? C3 C4 C5 C6 -0.6(8) . . . . ? C2 N1 C6 C5 1.1(6) . . . . ? C2 N1 C6 C7 -176.6(4) . . . . ? C4 C5 C6 N1 -0.3(7) . . . . ? C4 C5 C6 C7 177.4(5) . . . . ? N1 C6 C7 C8 -21.9(7) . . . . ? C5 C6 C7 C8 160.4(5) . . . . ? C6 C7 C8 N2 -49.9(6) . . . . ? C6 C7 C8 C10 62.0(6) . . . . ? C6 C7 C8 C9 -176.4(5) . . . . ? N2 C8 C10 O1 176.0(5) . . . . ? C7 C8 C10 O1 54.6(7) . . . . ? C9 C8 C10 O1 -66.6(6) . . . . ? N2 C8 C10 O2 -8.3(5) . . . . ? C7 C8 C10 O2 -129.8(4) . . . . ? C9 C8 C10 O2 109.0(5) . . . . ? O1 C10 O2 C11 -174.3(5) . . . . ? C8 C10 O2 C11 9.9(5) . . . . ? C10 O2 C11 N2 -6.7(5) . . . . ? C10 O2 C11 C12 -128.7(4) . . . . ? O2 C11 C12 C17 -122.4(5) . . . . ? N2 C11 C12 C17 122.3(5) . . . . ? O2 C11 C12 C13 58.0(6) . . . . ? N2 C11 C12 C13 -57.4(6) . . . . ? C17 C12 C13 C14 -0.4(8) . . . . ? C11 C12 C13 C14 179.3(5) . . . . ? C12 C13 C14 C15 -0.6(10) . . . . ? C13 C14 C15 C16 1.1(11) . . . . ? C14 C15 C16 C17 -0.7(11) . . . . ? C13 C12 C17 C16 0.9(8) . . . . ? C11 C12 C17 C16 -178.8(5) . . . . ? C15 C16 C17 C12 -0.4(10) . . . . ? O2 C11 N2 C18 171.4(4) . . . . ? C12 C11 N2 C18 -69.5(5) . . . . ? O2 C11 N2 C8 0.9(4) . . . . ? C12 C11 N2 C8 120.0(4) . . . . ? C7 C8 N2 C18 -47.8(6) . . . . ? C10 C8 N2 C18 -166.3(4) . . . . ? C9 C8 N2 C18 77.5(5) . . . . ? C7 C8 N2 C11 122.7(5) . . . . ? C10 C8 N2 C11 4.2(4) . . . . ? C9 C8 N2 C11 -112.0(5) . . . . ? C11 N2 C18 O3 177.0(4) . . . . ? C8 N2 C18 O3 -13.5(7) . . . . ? C11 N2 C18 O4 -2.5(5) . . . . ? C8 N2 C18 O4 167.0(4) . . . . ? O3 C18 O4 C19 -0.2(6) . . . . ? N2 C18 O4 C19 179.3(4) . . . . ? C18 O4 C19 C20 76.9(5) . . . . ? O4 C19 C20 C21 8.0(7) . . . . ? O4 C19 C20 C25 -172.1(6) . . . . ? C25 C20 C21 C22 0.1(9) . . . . ? C19 C20 C21 C22 -179.9(6) . . . . ? C20 C21 C22 C23 -1.7(10) . . . . ? C21 C22 C23 C24 3.1(12) . . . . ? C22 C23 C24 C25 -3.0(15) . . . . ? C21 C20 C25 C24 -0.1(12) . . . . ? C19 C20 C25 C24 -180.0(8) . . . . ? C23 C24 C25 C20 1.5(16) . . . . ? Br2 C26 C27 N3 84.7(4) . . . . ? Br2 C26 C27 C28 -95.1(5) . . . . ? C28 C27 N3 C31 0.6(6) . . . . ? C26 C27 N3 C31 -179.2(4) . . . . ? N3 C27 C28 C29 -0.7(7) . . . . ? C26 C27 C28 C29 179.1(5) . . . . ? C27 C28 C29 C30 -0.1(8) . . . . ? C28 C29 C30 C31 0.9(8) . . . . ? C27 N3 C31 C30 0.3(6) . . . . ? C27 N3 C31 C32 -177.8(4) . . . . ? C29 C30 C31 N3 -1.1(7) . . . . ? C29 C30 C31 C32 176.9(5) . . . . ? N3 C31 C32 C33 -19.0(6) . . . . ? C30 C31 C32 C33 162.9(4) . . . . ? C31 C32 C33 N4 -50.7(5) . . . . ? C31 C32 C33 C35 62.7(5) . . . . ? C31 C32 C33 C34 -176.3(4) . . . . ? N4 C33 C35 O5 -179.2(4) . . . . ? C32 C33 C35 O5 59.0(6) . . . . ? C34 C33 C35 O5 -61.9(6) . . . . ? N4 C33 C35 O6 -4.1(4) . . . . ? C32 C33 C35 O6 -125.8(4) . . . . ? C34 C33 C35 O6 113.2(4) . . . . ? O5 C35 O6 C36 -177.1(4) . . . . ? C33 C35 O6 C36 7.4(4) . . . . ? C35 O6 C36 N4 -7.3(4) . . . . ? C35 O6 C36 C37 -131.2(4) . . . . ? O6 C36 C37 C42 56.5(6) . . . . ? N4 C36 C37 C42 -59.6(6) . . . . ? O6 C36 C37 C38 -121.5(5) . . . . ? N4 C36 C37 C38 122.4(5) . . . . ? C42 C37 C38 C39 0.6(8) . . . . ? C36 C37 C38 C39 178.6(5) . . . . ? C37 C38 C39 C40 -1.1(10) . . . . ? C38 C39 C40 C41 2.2(11) . . . . ? C39 C40 C41 C42 -2.7(12) . . . . ? C38 C37 C42 C41 -1.1(9) . . . . ? C36 C37 C42 C41 -179.1(6) . . . . ? C40 C41 C42 C37 2.2(11) . . . . ? O6 C36 N4 C43 172.6(3) . . . . ? C37 C36 N4 C43 -68.1(5) . . . . ? O6 C36 N4 C33 4.6(4) . . . . ? C37 C36 N4 C33 123.9(4) . . . . ? C35 C33 N4 C43 -168.8(3) . . . . ? C32 C33 N4 C43 -48.7(5) . . . . ? C34 C33 N4 C43 75.6(5) . . . . ? C35 C33 N4 C36 -0.6(4) . . . . ? C32 C33 N4 C36 119.4(4) . . . . ? C34 C33 N4 C36 -116.3(4) . . . . ? C36 N4 C43 O7 -178.4(4) . . . . ? C33 N4 C43 O7 -11.6(7) . . . . ? C36 N4 C43 O8 2.4(5) . . . . ? C33 N4 C43 O8 169.2(3) . . . . ? O7 C43 O8 C44 -4.9(7) . . . . ? N4 C43 O8 C44 174.4(4) . . . . ? C43 O8 C44 C45 92.3(5) . . . . ? O8 C44 C45 C50 85.6(7) . . . . ? O8 C44 C45 C46 -100.5(6) . . . . ? C50 C45 C46 C47 -3.2(10) . . . . ? C44 C45 C46 C47 -177.0(6) . . . . ? C45 C46 C47 C48 -0.1(12) . . . . ? C46 C47 C48 C49 1.9(14) . . . . ? C47 C48 C49 C50 -0.6(15) . . . . ? C46 C45 C50 C49 4.6(12) . . . . ? C44 C45 C50 C49 178.5(7) . . . . ? C48 C49 C50 C45 -2.7(14) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 24.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.487 _refine_diff_density_min -0.471 _refine_diff_density_rms 0.044 # Attachment 'Dungan_Oxazolidinone_10.cif' data_rut06fpm _database_code_depnum_ccdc_archive 'CCDC 752805' #TrackingRef 'Dungan_Oxazolidinone_10.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H17 N O4' _chemical_formula_weight 311.33 _chemical_absolute_configuration syn loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 6.4808(6) _cell_length_b 15.2360(13) _cell_length_c 15.7084(14) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1551.1(2) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 8246 _cell_measurement_theta_min 2.59 _cell_measurement_theta_max 26.37 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.333 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 656 _exptl_absorpt_coefficient_mu 0.095 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8590 _exptl_absorpt_correction_T_max 0.9991 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean 8.366 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 25949 _diffrn_reflns_av_R_equivalents 0.0352 _diffrn_reflns_av_sigmaI/netI 0.0150 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.86 _diffrn_reflns_theta_max 26.99 _reflns_number_total 1967 _reflns_number_gt 1865 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0440P)^2^+0.3645P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1967 _refine_ls_number_parameters 209 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0333 _refine_ls_R_factor_gt 0.0310 _refine_ls_wR_factor_ref 0.0782 _refine_ls_wR_factor_gt 0.0767 _refine_ls_goodness_of_fit_ref 1.065 _refine_ls_restrained_S_all 1.065 _refine_ls_shift/su_max 0.006 _refine_ls_shift/su_mean 0.001 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.4305(3) 0.41003(12) 0.75223(13) 0.0290(4) Uani 1 1 d . . . H1 H 0.3856 0.4402 0.8018 0.035 Uiso 1 1 calc R . . C2 C 0.2973(4) 0.39954(14) 0.68414(14) 0.0361(5) Uani 1 1 d . . . H2 H 0.1617 0.4230 0.6869 0.043 Uiso 1 1 calc R . . C3 C 0.3614(4) 0.35491(14) 0.61198(14) 0.0395(5) Uani 1 1 d . . . H3 H 0.2697 0.3476 0.5653 0.047 Uiso 1 1 calc R . . C4 C 0.5585(4) 0.32116(13) 0.60811(13) 0.0368(5) Uani 1 1 d . . . H4 H 0.6022 0.2903 0.5588 0.044 Uiso 1 1 calc R . . C5 C 0.6923(4) 0.33196(12) 0.67543(12) 0.0301(4) Uani 1 1 d . . . H5 H 0.8282 0.3088 0.6721 0.036 Uiso 1 1 calc R . . C6 C 0.6300(3) 0.37661(11) 0.74839(12) 0.0251(4) Uani 1 1 d . . . C7 C 0.7770(3) 0.39015(11) 0.82084(12) 0.0239(4) Uani 1 1 d . . . H7A H 0.8885 0.4306 0.8029 0.029 Uiso 1 1 calc R . . H7B H 0.7032 0.4174 0.8693 0.029 Uiso 1 1 calc R . . O1 O 0.8668(2) 0.30660(8) 0.84789(8) 0.0219(3) Uani 1 1 d . . . O2 O 0.5912(2) 0.28339(8) 0.93396(8) 0.0227(3) Uani 1 1 d . . . C8 C 0.7480(3) 0.25813(11) 0.89941(10) 0.0178(3) Uani 1 1 d . . . N N 0.8244(2) 0.17571(9) 0.90764(9) 0.0165(3) Uani 1 1 d . . . C9 C 0.7546(3) 0.12013(11) 0.97756(10) 0.0172(3) Uani 1 1 d . . . H9 H 0.7553 0.1548 1.0316 0.021 Uiso 1 1 calc R . . C10 C 0.5425(3) 0.07988(12) 0.96446(11) 0.0203(4) Uani 1 1 d . . . H10A H 0.4380 0.1264 0.9645 0.030 Uiso 1 1 calc R . . H10B H 0.5135 0.0384 1.0106 0.030 Uiso 1 1 calc R . . H10C H 0.5391 0.0489 0.9098 0.030 Uiso 1 1 calc R . . C11 C 0.9236(3) 0.05189(12) 0.98071(10) 0.0185(3) Uani 1 1 d . . . O3 O 0.9333(2) -0.01123(8) 1.02557(8) 0.0257(3) Uani 1 1 d . . . O4 O 1.07037(18) 0.06986(8) 0.92251(7) 0.0197(3) Uani 1 1 d . . . C12 C 1.0339(3) 0.15293(11) 0.88060(10) 0.0169(3) Uani 1 1 d . . . H12 H 1.1335 0.1978 0.9022 0.020 Uiso 1 1 calc R . . C13 C 1.0639(3) 0.14035(11) 0.78638(10) 0.0167(3) Uani 1 1 d . . . C14 C 0.9039(3) 0.11588(11) 0.73271(11) 0.0205(4) Uani 1 1 d . . . H14 H 0.7680 0.1096 0.7545 0.025 Uiso 1 1 calc R . . C15 C 0.9430(3) 0.10072(12) 0.64743(11) 0.0238(4) Uani 1 1 d . . . H15 H 0.8332 0.0850 0.6104 0.029 Uiso 1 1 calc R . . C16 C 1.1420(3) 0.10844(11) 0.61585(11) 0.0233(4) Uani 1 1 d . . . H16 H 1.1686 0.0969 0.5574 0.028 Uiso 1 1 calc R . . C17 C 1.3014(3) 0.13279(11) 0.66897(12) 0.0231(4) Uani 1 1 d . . . H17 H 1.4377 0.1379 0.6473 0.028 Uiso 1 1 calc R . . C18 C 1.2622(3) 0.14984(11) 0.75415(11) 0.0203(3) Uani 1 1 d . . . H18 H 1.3712 0.1680 0.7905 0.024 Uiso 1 1 calc 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 C1 0.0333(10) 0.0258(9) 0.0278(9) 0.0049(8) 0.0049(9) 0.0012(9) C2 0.0349(11) 0.0340(10) 0.0393(12) 0.0104(9) -0.0027(10) -0.0009(10) C3 0.0574(15) 0.0290(10) 0.0322(11) 0.0094(9) -0.0134(11) -0.0090(11) C4 0.0624(15) 0.0236(9) 0.0245(9) 0.0021(8) 0.0018(11) -0.0028(11) C5 0.0402(12) 0.0225(9) 0.0277(10) 0.0016(7) 0.0071(9) -0.0001(9) C6 0.0345(10) 0.0165(8) 0.0243(9) 0.0048(7) 0.0049(8) -0.0027(8) C7 0.0279(9) 0.0172(8) 0.0267(9) 0.0004(7) 0.0052(8) -0.0010(8) O1 0.0207(6) 0.0200(6) 0.0249(6) 0.0005(5) 0.0048(5) 0.0005(5) O2 0.0202(6) 0.0248(6) 0.0231(6) -0.0018(5) 0.0057(5) 0.0042(5) C8 0.0164(8) 0.0215(8) 0.0156(7) -0.0038(6) -0.0006(6) -0.0009(7) N 0.0121(6) 0.0209(7) 0.0165(7) -0.0005(5) 0.0013(5) 0.0005(6) C9 0.0146(8) 0.0224(8) 0.0148(7) -0.0007(6) 0.0000(6) -0.0001(7) C10 0.0122(7) 0.0252(8) 0.0234(8) 0.0020(7) 0.0005(7) -0.0015(7) C11 0.0112(7) 0.0281(9) 0.0161(8) -0.0006(7) -0.0028(6) -0.0019(7) O3 0.0188(6) 0.0318(7) 0.0264(6) 0.0092(5) -0.0014(6) 0.0022(6) O4 0.0136(5) 0.0248(6) 0.0208(6) 0.0026(5) -0.0001(5) 0.0030(5) C12 0.0114(7) 0.0198(8) 0.0195(8) -0.0006(6) -0.0010(6) 0.0003(6) C13 0.0165(8) 0.0153(7) 0.0183(8) -0.0006(6) 0.0000(7) 0.0023(6) C14 0.0151(8) 0.0239(8) 0.0225(8) -0.0039(7) -0.0005(7) 0.0015(7) C15 0.0254(9) 0.0248(9) 0.0213(9) -0.0039(7) -0.0056(8) 0.0022(8) C16 0.0344(10) 0.0190(8) 0.0165(8) -0.0013(6) 0.0045(8) 0.0028(8) C17 0.0221(9) 0.0221(8) 0.0251(9) 0.0012(7) 0.0088(7) -0.0007(7) C18 0.0170(8) 0.0218(8) 0.0221(8) -0.0014(7) 0.0000(7) -0.0020(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.384(3) . ? C1 C6 1.390(3) . ? C1 H1 0.9500 . ? C2 C3 1.385(3) . ? C2 H2 0.9500 . ? C3 C4 1.378(4) . ? C3 H3 0.9500 . ? C4 C5 1.378(3) . ? C4 H4 0.9500 . ? C5 C6 1.393(3) . ? C5 H5 0.9500 . ? C6 C7 1.499(3) . ? C7 O1 1.463(2) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? O1 C8 1.339(2) . ? O2 C8 1.215(2) . ? C8 N 1.356(2) . ? N C9 1.459(2) . ? N C12 1.465(2) . ? C9 C11 1.511(2) . ? C9 C10 1.519(2) . ? C9 H9 1.0000 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 O3 1.194(2) . ? C11 O4 1.347(2) . ? O4 C12 1.446(2) . ? C12 C13 1.505(2) . ? C12 H12 1.0000 . ? C13 C14 1.387(2) . ? C13 C18 1.389(2) . ? C14 C15 1.383(2) . ? C14 H14 0.9500 . ? C15 C16 1.387(3) . ? C15 H15 0.9500 . ? C16 C17 1.379(3) . ? C16 H16 0.9500 . ? C17 C18 1.387(2) . ? C17 H17 0.9500 . ? C18 H18 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C6 120.27(19) . . ? C2 C1 H1 119.9 . . ? C6 C1 H1 119.9 . . ? C1 C2 C3 120.1(2) . . ? C1 C2 H2 119.9 . . ? C3 C2 H2 119.9 . . ? C4 C3 C2 119.8(2) . . ? C4 C3 H3 120.1 . . ? C2 C3 H3 120.1 . . ? C5 C4 C3 120.3(2) . . ? C5 C4 H4 119.8 . . ? C3 C4 H4 119.8 . . ? C4 C5 C6 120.5(2) . . ? C4 C5 H5 119.8 . . ? C6 C5 H5 119.8 . . ? C1 C6 C5 118.97(19) . . ? C1 C6 C7 120.52(17) . . ? C5 C6 C7 120.50(19) . . ? O1 C7 C6 110.73(14) . . ? O1 C7 H7A 109.5 . . ? C6 C7 H7A 109.5 . . ? O1 C7 H7B 109.5 . . ? C6 C7 H7B 109.5 . . ? H7A C7 H7B 108.1 . . ? C8 O1 C7 115.26(14) . . ? O2 C8 O1 125.19(16) . . ? O2 C8 N 123.80(16) . . ? O1 C8 N 111.01(14) . . ? C8 N C9 119.75(14) . . ? C8 N C12 122.02(14) . . ? C9 N C12 111.60(13) . . ? N C9 C11 101.50(13) . . ? N C9 C10 114.38(14) . . ? C11 C9 C10 112.50(14) . . ? N C9 H9 109.4 . . ? C11 C9 H9 109.4 . . ? C10 C9 H9 109.4 . . ? C9 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C9 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? O3 C11 O4 121.83(16) . . ? O3 C11 C9 127.70(15) . . ? O4 C11 C9 110.46(14) . . ? C11 O4 C12 111.81(13) . . ? O4 C12 N 103.12(13) . . ? O4 C12 C13 108.38(14) . . ? N C12 C13 115.79(14) . . ? O4 C12 H12 109.8 . . ? N C12 H12 109.8 . . ? C13 C12 H12 109.8 . . ? C14 C13 C18 119.87(15) . . ? C14 C13 C12 122.37(16) . . ? C18 C13 C12 117.69(16) . . ? C15 C14 C13 119.79(17) . . ? C15 C14 H14 120.1 . . ? C13 C14 H14 120.1 . . ? C14 C15 C16 120.18(18) . . ? C14 C15 H15 119.9 . . ? C16 C15 H15 119.9 . . ? C17 C16 C15 120.21(16) . . ? C17 C16 H16 119.9 . . ? C15 C16 H16 119.9 . . ? C16 C17 C18 119.80(17) . . ? C16 C17 H17 120.1 . . ? C18 C17 H17 120.1 . . ? C17 C18 C13 120.12(17) . . ? C17 C18 H18 119.9 . . ? C13 C18 H18 119.9 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 0.6(3) . . . . ? C1 C2 C3 C4 -0.2(3) . . . . ? C2 C3 C4 C5 -0.3(3) . . . . ? C3 C4 C5 C6 0.4(3) . . . . ? C2 C1 C6 C5 -0.5(3) . . . . ? C2 C1 C6 C7 178.12(17) . . . . ? C4 C5 C6 C1 0.1(3) . . . . ? C4 C5 C6 C7 -178.61(17) . . . . ? C1 C6 C7 O1 128.01(17) . . . . ? C5 C6 C7 O1 -53.4(2) . . . . ? C6 C7 O1 C8 -80.91(19) . . . . ? C7 O1 C8 O2 -11.3(2) . . . . ? C7 O1 C8 N 168.01(13) . . . . ? O2 C8 N C9 -17.6(2) . . . . ? O1 C8 N C9 163.11(14) . . . . ? O2 C8 N C12 -166.63(16) . . . . ? O1 C8 N C12 14.1(2) . . . . ? C8 N C9 C11 -161.32(14) . . . . ? C12 N C9 C11 -9.29(16) . . . . ? C8 N C9 C10 77.28(19) . . . . ? C12 N C9 C10 -130.69(14) . . . . ? N C9 C11 O3 -176.48(17) . . . . ? C10 C9 C11 O3 -53.8(2) . . . . ? N C9 C11 O4 2.18(17) . . . . ? C10 C9 C11 O4 124.89(16) . . . . ? O3 C11 O4 C12 -175.48(16) . . . . ? C9 C11 O4 C12 5.76(18) . . . . ? C11 O4 C12 N -11.07(16) . . . . ? C11 O4 C12 C13 -134.31(15) . . . . ? C8 N C12 O4 163.88(14) . . . . ? C9 N C12 O4 12.58(16) . . . . ? C8 N C12 C13 -77.95(19) . . . . ? C9 N C12 C13 130.75(16) . . . . ? O4 C12 C13 C14 89.64(19) . . . . ? N C12 C13 C14 -25.6(2) . . . . ? O4 C12 C13 C18 -87.22(18) . . . . ? N C12 C13 C18 157.56(15) . . . . ? C18 C13 C14 C15 0.3(3) . . . . ? C12 C13 C14 C15 -176.54(17) . . . . ? C13 C14 C15 C16 1.1(3) . . . . ? C14 C15 C16 C17 -1.2(3) . . . . ? C15 C16 C17 C18 -0.2(3) . . . . ? C16 C17 C18 C13 1.6(3) . . . . ? C14 C13 C18 C17 -1.6(3) . . . . ? C12 C13 C18 C17 175.33(16) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 26.99 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.285 _refine_diff_density_min -0.145 _refine_diff_density_rms 0.037