#------------------------------------------------------------------------------ #$Date: 2014-07-05 15:17:00 +0300 (Sat, 05 Jul 2014) $ #$Revision: 119289 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/51/64/1516477.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_1516477 loop_ _publ_author_name 'Medina, Florian' 'Besnard, C\'eline' 'Lacour, J\'er\^ome' _publ_section_title ; One-Step Synthesis of Nitrogen-Containing Medium-Sized Rings via \a-Imino Diazo Intermediates. ; _journal_issue 12 _journal_name_full 'Organic letters' _journal_page_first 3232 _journal_page_last 3235 _journal_paper_doi 10.1021/ol5012532 _journal_volume 16 _journal_year 2014 _chemical_formula_moiety 'C18 H18 Br N O4 S' _chemical_formula_sum 'C18 H18 Br N O4 S' _chemical_formula_weight 424.30 _chemical_name_systematic ; ? ; _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2ybc' _space_group_name_H-M_alt 'P 1 21/c 1' _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 1 21/c 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary iterative _audit_creation_date 2013-04-10 _audit_creation_method ; Olex2 1.2-beta (compiled Mar 21 2013 11:17:50, GUI svn.r4446) ; _cell_angle_alpha 90 _cell_angle_beta 97.3759(12) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 12.50619(17) _cell_length_b 11.55718(16) _cell_length_c 12.58675(17) _cell_measurement_reflns_used 4070 _cell_measurement_temperature 201(5) _cell_measurement_theta_max 73.1220 _cell_measurement_theta_min 5.1930 _cell_volume 1804.19(4) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44) ; _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement ; SHELXL, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _computing_structure_solution ; olex2.solve (L.J. Bourhis, O.V. Dolomanov, R.J. Gildea, J.A.K. Howard, H. Puschmann, in preparation, 2011) ; _diffrn_ambient_temperature 201(5) _diffrn_detector_area_resol_mean 10.4679 _diffrn_measured_fraction_theta_full 0.9991 _diffrn_measured_fraction_theta_max 0.9691 _diffrn_measurement_details ; 1 omega -123.00 -79.00 0.5000 0.5000 omega____ theta____ kappa____ phi______ frames - -38.9365 -99.0000 -120.0000 88 2 omega -119.00 -93.00 0.5000 0.5000 omega____ theta____ kappa____ phi______ frames - -38.9365 -99.0000 30.0000 52 3 omega -97.00 -11.00 0.5000 0.5000 omega____ theta____ kappa____ phi______ frames - -38.9365 -38.0000 90.0000 172 4 omega -124.00 -90.00 0.5000 0.5000 omega____ theta____ kappa____ phi______ frames - -38.9365 -99.0000 -60.0000 68 5 omega -132.00 -79.00 0.5000 0.5000 omega____ theta____ kappa____ phi______ frames - -38.9365 -178.0000 0.0000 106 6 omega -41.00 -5.00 0.5000 0.8000 omega____ theta____ kappa____ phi______ frames - -68.5000 30.0000 30.0000 72 7 omega 41.00 99.00 0.5000 0.8000 omega____ theta____ kappa____ phi______ frames - 109.7499 -94.0000 -150.0000 116 8 omega 52.00 90.00 0.5000 0.8000 omega____ theta____ kappa____ phi______ frames - 109.7499 -45.0000 60.0000 76 9 omega 29.00 91.00 0.5000 0.8000 omega____ theta____ kappa____ phi______ frames - 109.7499 -30.0000 150.0000 124 10 omega 32.00 95.00 0.5000 0.8000 omega____ theta____ kappa____ phi______ frames - 109.7499 -45.0000 -90.0000 126 11 omega 58.00 84.00 0.5000 0.8000 omega____ theta____ kappa____ phi______ frames - 109.7499 -30.0000 -150.0000 52 12 omega 74.00 176.00 0.5000 0.8000 omega____ theta____ kappa____ phi______ frames - 109.7499 30.0000 60.0000 204 13 omega 56.00 103.00 0.5000 0.8000 omega____ theta____ kappa____ phi______ frames - 109.7499 -94.0000 -60.0000 94 ; _diffrn_measurement_device_type 'SuperNova, Dual, Cu at zero, Atlas' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 -0.0346776000 _diffrn_orient_matrix_UB_12 0.0603227000 _diffrn_orient_matrix_UB_13 -0.1080772000 _diffrn_orient_matrix_UB_21 0.1190319000 _diffrn_orient_matrix_UB_22 0.0111810000 _diffrn_orient_matrix_UB_23 -0.0181089000 _diffrn_orient_matrix_UB_31 -0.0064702000 _diffrn_orient_matrix_UB_32 -0.1184083000 _diffrn_orient_matrix_UB_33 -0.0567721000 _diffrn_radiation_monochromator mirror _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.5418 _diffrn_reflns_av_R_equivalents 0.0179 _diffrn_reflns_av_unetI/netI 0.0230 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_number 6236 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 73.176 _diffrn_reflns_theta_min 3.564 _diffrn_source 'SuperNova (Cu) X-ray Source' _exptl_absorpt_coefficient_mu 4.387 _exptl_absorpt_correction_T_max 0.754 _exptl_absorpt_correction_T_min 0.280 _exptl_absorpt_correction_type analytical _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44) 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) followed by a multu-scan correction (ABSPACK) ; _exptl_crystal_colour colourless _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.562 _exptl_crystal_description plate _exptl_crystal_F_000 864 _exptl_crystal_size_max 0.4117 _exptl_crystal_size_mid 0.3699 _exptl_crystal_size_min 0.064 _refine_diff_density_max 0.514 _refine_diff_density_min -0.651 _refine_diff_density_rms 0.061 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.055 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 227 _refine_ls_number_reflns 3509 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.055 _refine_ls_R_factor_all 0.0372 _refine_ls_R_factor_gt 0.0339 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details ; w=1/[\s^2^(Fo^2^)+(0.0461P)^2^+0.9475P] where P=(Fo^2^+2Fc^2^)/3 ; _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0865 _refine_ls_wR_factor_ref 0.0891 _reflns_Friedel_coverage 0.000 _reflns_number_gt 3224 _reflns_number_total 3509 _reflns_threshold_expression 'I > 2\s(I)' _[local]_cod_data_source_file ol5012532_si_003.cif _[local]_cod_data_source_block fm127-1 _cod_depositor_comments 'Adding full bibliography for 1516477--1516478.cif.' _cod_database_code 1516477 _chemical_oxdiff_formula 'C18 H18 Br1 S1 O4 N1' _diffrn_reflns_laue_measured_fraction_full 0.998 _diffrn_reflns_laue_measured_fraction_max 0.969 _diffrn_reflns_point_group_measured_fraction_full 0.998 _diffrn_reflns_point_group_measured_fraction_max 0.969 _reflns_odcompleteness_completeness 99.91 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 66.97 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups At 1.5 times of: All C(H,H,H) groups 2.a Ternary CH refined with riding coordinates: C9(H9) 2.b Secondary CH2 refined with riding coordinates: C8(H8A,H8B), C11(H11A,H11B) 2.c Aromatic/amide H refined with riding coordinates: C19(H19), C5(H5), C16(H16), C15(H15), C22(H22), C20(H20), C17(H17), C14(H14), C23(H23), C13(H13) 2.d Idealised Me refined as rotating group: C25(H25A,H25B,H25C) ; _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; _shelxl_version_number 2013-2 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' 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_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp Br24 Br -0.13101(2) 0.68718(3) 0.62137(2) 0.04968(11) Uani 1 1 d . . S1 S 0.27703(4) 0.61132(5) 0.37009(4) 0.03207(13) Uani 1 1 d . . O7 O 0.38872(14) 0.93267(14) 0.53247(14) 0.0431(4) Uani 1 1 d . . O3 O 0.33795(13) 0.51660(13) 0.42003(14) 0.0391(4) Uani 1 1 d . . O2 O 0.24212(14) 0.61104(17) 0.25754(13) 0.0451(4) Uani 1 1 d . . O10 O 0.23500(14) 0.88293(15) 0.32655(13) 0.0422(4) Uani 1 1 d . . N4 N 0.35101(15) 0.72809(16) 0.39667(14) 0.0311(4) Uani 1 1 d . . C19 C 0.17272(19) 0.6095(2) 0.54657(18) 0.0369(5) Uani 1 1 d . . H19 H 0.2392 0.5833 0.5837 0.044 Uiso 1 1 calc R U C8 C 0.2720(2) 0.9346(2) 0.51699(19) 0.0416(5) Uani 1 1 d . . H8A H 0.2461 0.9890 0.5688 0.050 Uiso 1 1 calc R U H8B H 0.2444 0.8566 0.5311 0.050 Uiso 1 1 calc R U C5 C 0.41729(17) 0.73343(19) 0.49621(16) 0.0307(4) Uani 1 1 d . . H5 H 0.4508 0.6635 0.5225 0.037 Uiso 1 1 calc R U C16 C 0.6560(2) 0.7381(3) 0.7770(2) 0.0462(6) Uani 1 1 d . . H16 H 0.7054 0.6763 0.7935 0.055 Uiso 1 1 calc R U C21 C -0.01122(19) 0.6644(2) 0.54531(19) 0.0360(5) Uani 1 1 d . . C15 C 0.6505(2) 0.8269(3) 0.8504(2) 0.0486(6) Uani 1 1 d . . H15 H 0.6960 0.8261 0.9170 0.058 Uiso 1 1 calc R U C22 C -0.02197(19) 0.6830(2) 0.4360(2) 0.0414(5) Uani 1 1 d . . H22 H -0.0891 0.7069 0.3986 0.050 Uiso 1 1 calc R U C6 C 0.43710(17) 0.82764(18) 0.55668(17) 0.0310(4) Uani 1 1 d . . C20 C 0.0852(2) 0.6279(2) 0.60153(18) 0.0399(5) Uani 1 1 d . . H20 H 0.0913 0.6157 0.6767 0.048 Uiso 1 1 calc R U C17 C 0.58992(18) 0.7391(2) 0.67979(19) 0.0389(5) Uani 1 1 d . . H17 H 0.5954 0.6790 0.6293 0.047 Uiso 1 1 calc R U C9 C 0.2286(2) 0.9710(2) 0.4049(2) 0.0425(5) Uani 1 1 d . . H9 H 0.2684 1.0411 0.3849 0.051 Uiso 1 1 calc R U C14 C 0.5784(2) 0.9164(2) 0.8260(2) 0.0449(6) Uani 1 1 d . . H14 H 0.5750 0.9778 0.8757 0.054 Uiso 1 1 calc R U C23 C 0.06591(19) 0.6662(2) 0.38168(18) 0.0376(5) Uani 1 1 d . . H23 H 0.0601 0.6799 0.3067 0.045 Uiso 1 1 calc R U C18 C 0.16306(17) 0.62923(18) 0.43759(17) 0.0305(4) Uani 1 1 d . . C11 C 0.3346(2) 0.8272(2) 0.32419(17) 0.0377(5) Uani 1 1 d . . H11A H 0.3933 0.8838 0.3436 0.045 Uiso 1 1 calc R U H11B H 0.3395 0.8007 0.2502 0.045 Uiso 1 1 calc R U C13 C 0.51080(18) 0.9173(2) 0.72946(18) 0.0366(5) Uani 1 1 d . . H13 H 0.4612 0.9791 0.7137 0.044 Uiso 1 1 calc R U C12 C 0.51513(17) 0.82833(19) 0.65565(17) 0.0311(4) Uani 1 1 d . . C25 C 0.1093(2) 0.9995(3) 0.3994(3) 0.0582(7) Uani 1 1 d . . H25A H 0.0812 1.0227 0.3262 0.087 Uiso 1 1 calc R U H25B H 0.0997 1.0632 0.4488 0.087 Uiso 1 1 calc R U H25C H 0.0702 0.9312 0.4196 0.087 Uiso 1 1 calc R U 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 Br24 0.04119(16) 0.05224(19) 0.05903(19) -0.01163(12) 0.01959(12) -0.00849(11) S1 0.0348(3) 0.0314(3) 0.0302(3) -0.0071(2) 0.0051(2) -0.0018(2) O7 0.0496(10) 0.0267(8) 0.0498(9) -0.0041(7) -0.0063(8) 0.0023(7) O3 0.0392(8) 0.0271(8) 0.0513(9) -0.0081(7) 0.0066(7) 0.0011(6) O2 0.0468(10) 0.0583(11) 0.0304(8) -0.0135(7) 0.0062(7) -0.0061(8) O10 0.0491(10) 0.0391(9) 0.0362(8) 0.0017(7) -0.0030(7) 0.0070(8) N4 0.0368(9) 0.0286(9) 0.0282(8) -0.0008(7) 0.0058(7) -0.0016(8) C19 0.0359(11) 0.0404(13) 0.0333(11) 0.0008(9) -0.0002(9) 0.0013(9) C8 0.0475(13) 0.0404(13) 0.0376(12) -0.0019(10) 0.0083(10) 0.0110(11) C5 0.0337(10) 0.0274(10) 0.0316(10) 0.0007(8) 0.0061(8) -0.0009(8) C16 0.0378(12) 0.0554(16) 0.0446(13) 0.0050(12) 0.0018(10) 0.0032(11) C21 0.0350(11) 0.0345(12) 0.0397(12) -0.0061(9) 0.0092(9) -0.0068(9) C15 0.0367(13) 0.0712(19) 0.0369(12) -0.0018(12) 0.0009(10) -0.0073(12) C22 0.0315(12) 0.0477(14) 0.0436(13) 0.0016(11) -0.0011(10) -0.0008(10) C6 0.0336(11) 0.0273(10) 0.0323(10) 0.0001(8) 0.0054(8) -0.0006(8) C20 0.0440(13) 0.0450(14) 0.0312(11) -0.0005(10) 0.0066(9) -0.0044(10) C17 0.0351(11) 0.0405(13) 0.0412(12) -0.0035(10) 0.0047(9) 0.0010(10) C9 0.0506(14) 0.0335(12) 0.0428(13) 0.0039(10) 0.0036(11) 0.0037(10) C14 0.0374(12) 0.0579(16) 0.0401(12) -0.0146(11) 0.0075(10) -0.0092(11) C23 0.0377(12) 0.0427(13) 0.0312(10) 0.0023(9) -0.0001(9) -0.0028(10) C18 0.0325(10) 0.0279(10) 0.0310(10) -0.0038(8) 0.0034(8) -0.0033(8) C11 0.0494(13) 0.0382(12) 0.0269(10) 0.0041(9) 0.0105(9) 0.0002(10) C13 0.0322(11) 0.0367(12) 0.0418(12) -0.0067(10) 0.0076(9) -0.0065(9) C12 0.0296(10) 0.0314(11) 0.0332(10) -0.0004(8) 0.0074(8) -0.0048(8) C25 0.0533(16) 0.0490(16) 0.0696(18) -0.0063(14) -0.0028(14) 0.0147(13) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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' Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist _exptl_oxdiff_crystal_face_indexfrac_h _exptl_oxdiff_crystal_face_indexfrac_k _exptl_oxdiff_crystal_face_indexfrac_l _exptl_oxdiff_crystal_face_x _exptl_oxdiff_crystal_face_y _exptl_oxdiff_crystal_face_z 0 0 -1 0.2255 0.0000 -0.0000 -1.0000 0.1081 0.0181 0.0568 0 0 1 0.1746 -0.0000 0.0000 1.0000 -0.1081 -0.0181 -0.0568 0 1 -1 0.1525 -0.0000 1.0000 -1.0000 0.1684 0.0293 -0.0616 -1 0 0 0.0246 -1.0000 -0.0000 -0.0000 0.0347 -0.1190 0.0065 1 0 0 0.0394 1.0000 0.0000 0.0000 -0.0347 0.1190 -0.0065 0 -1 0 0.1557 0.0000 -1.0000 0.0000 -0.0603 -0.0112 0.1184 0 1 0 0.2141 -0.0000 1.0000 -0.0000 0.0603 0.0112 -0.1184 loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle O3 S1 N4 106.50(9) O3 S1 C18 107.20(10) O2 S1 O3 120.76(11) O2 S1 N4 107.21(10) O2 S1 C18 108.38(10) N4 S1 C18 105.90(10) C6 O7 C8 116.84(18) C11 O10 C9 118.05(18) C5 N4 S1 117.82(15) C5 N4 C11 122.58(18) C11 N4 S1 119.04(15) C18 C19 C20 119.8(2) O7 C8 C9 111.5(2) C6 C5 N4 125.9(2) C17 C16 C15 120.4(2) C22 C21 Br24 119.93(18) C22 C21 C20 121.6(2) C20 C21 Br24 118.51(18) C14 C15 C16 119.5(2) C23 C22 C21 119.3(2) O7 C6 C12 113.96(18) C5 C6 O7 123.4(2) C5 C6 C12 122.6(2) C21 C20 C19 119.0(2) C16 C17 C12 120.3(2) O10 C9 C8 113.7(2) O10 C9 C25 105.4(2) C8 C9 C25 109.7(2) C15 C14 C13 120.5(2) C22 C23 C18 119.5(2) C19 C18 S1 119.11(17) C19 C18 C23 120.9(2) C23 C18 S1 120.01(17) O10 C11 N4 113.52(19) C14 C13 C12 120.5(2) C17 C12 C6 121.9(2) C13 C12 C6 119.2(2) C13 C12 C17 118.8(2) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance Br24 C21 1.897(2) S1 O3 1.4321(17) S1 O2 1.4279(17) S1 N4 1.6461(18) S1 C18 1.763(2) O7 C8 1.448(3) O7 C6 1.373(3) O10 C9 1.427(3) O10 C11 1.406(3) N4 C5 1.412(3) N4 C11 1.463(3) C19 C20 1.384(3) C19 C18 1.380(3) C8 C9 1.506(3) C5 C6 1.333(3) C16 C15 1.389(4) C16 C17 1.386(3) C21 C22 1.382(3) C21 C20 1.384(3) C15 C14 1.380(4) C22 C23 1.380(4) C6 C12 1.481(3) C17 C12 1.399(3) C9 C25 1.520(4) C14 C13 1.389(3) C23 C18 1.391(3) C13 C12 1.391(3)