#------------------------------------------------------------------------------ #$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $ #$Revision: 176729 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/50/72/1507263.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_1507263 loop_ _publ_author_name 'Reddy, P. Ganapati' 'Varghese, Babu' 'Baskaran, Sundarababu' _publ_section_title ; Epoxide-initiated electrophilic cyclization of azides: a novel route for the stereoselective construction of azabicyclic ring systems and total synthesis of (+/-)-indolizidine 167B and 209D. ; _journal_issue 4 _journal_name_full 'Organic letters' _journal_page_first 583 _journal_page_last 585 _journal_paper_doi 10.1021/ol027563v _journal_volume 5 _journal_year 2003 _chemical_formula_sum 'C16 H21 Br Cl N O2' _chemical_formula_weight 374.70 _chemical_name_systematic ; ? ; _space_group_IT_number 14 _symmetry_cell_setting monoclinic _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 direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-97 _cell_angle_alpha 90.00 _cell_angle_beta 97.29(6) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 11.517(7) _cell_length_b 7.363(10) _cell_length_c 18.932(11) _cell_measurement_reflns_used 25 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 15 _cell_measurement_theta_min 10 _cell_volume 1592(3) _computing_cell_refinement 'cad4 programs' _computing_data_collection 'cad4 programs' _computing_data_reduction 'XCAD4 (WINGX)' _computing_molecular_graphics 'ORTEP3 (WINGX)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXL-96 (Sheldrick, 1997)' _diffrn_ambient_temperature 293(2) _diffrn_measured_fraction_theta_full 0.997 _diffrn_measured_fraction_theta_max 0.997 _diffrn_measurement_device_type 'cad4 diffractometer' _diffrn_measurement_method 'omega twotheta' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0628 _diffrn_reflns_av_sigmaI/netI 0.1418 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_number 2952 _diffrn_reflns_theta_full 24.99 _diffrn_reflns_theta_max 24.99 _diffrn_reflns_theta_min 2.17 _diffrn_standards_decay_% 0 _diffrn_standards_interval_time '1 hour' _diffrn_standards_number 2 _exptl_absorpt_coefficient_mu 2.753 _exptl_absorpt_correction_T_max 0.9968 _exptl_absorpt_correction_T_min 0.6875 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_process_details ; North A.C.T., Phillips D.C. & Mathews F.S. (1968) Acta. Cryst. A24, 351 Number of psi-scan sets used was 1 Theta correction was applied. Averaged transmission function was used. No Fourier smoothing was applied. ; _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.563 _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 768 _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.2 _refine_diff_density_max 0.369 _refine_diff_density_min -0.486 _refine_diff_density_rms 0.088 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 0.850 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 163 _refine_ls_number_reflns 2804 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 0.850 _refine_ls_R_factor_all 0.1282 _refine_ls_R_factor_gt 0.0542 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0555P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1127 _refine_ls_wR_factor_ref 0.1268 _reflns_number_gt 1291 _reflns_number_total 2804 _reflns_threshold_expression >2sigma(I) _cod_data_source_file ol027563vsi20021227_091604.cif _cod_data_source_block greddy _cod_original_cell_volume 1592(2) _cod_original_sg_symbol_H-M P21/c _cod_database_code 1507263 #BEGIN Tags that were not found in dictionaries: _exptl_absorpt_factor_mur 0.000 #END Tags that were not found in dictionaries loop_ _symmetry_equiv_pos_as_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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags C1 C 0.6993(5) 0.8529(9) 0.3596(3) 0.0294(16) Uani 1 1 d . H1A H 0.7127 0.9177 0.4045 0.035 Uiso 1 1 calc R H1B H 0.7286 0.7299 0.3667 0.035 Uiso 1 1 calc R C2 C 0.5690(5) 0.8526(9) 0.3305(3) 0.0331(17) Uani 1 1 d . H2A H 0.5292 0.7464 0.3460 0.040 Uiso 1 1 calc R H2B H 0.5298 0.9616 0.3439 0.040 Uiso 1 1 calc R C3 C 0.5780(6) 0.8474(11) 0.2533(3) 0.043(2) Uani 1 1 d . H3A H 0.5323 0.9463 0.2301 0.051 Uiso 1 1 calc R H3B H 0.5447 0.7344 0.2337 0.051 Uiso 1 1 calc R C5 C 0.7404(7) 0.9400(11) 0.1725(4) 0.055(2) Uani 1 1 d . H5 H 0.7144 1.0665 0.1669 0.065 Uiso 1 1 calc R C6 C 0.8740(7) 0.9325(10) 0.1782(4) 0.049(2) Uani 1 1 d . H6A H 0.8990 0.8067 0.1780 0.059 Uiso 1 1 calc R H6B H 0.8994 0.9921 0.1371 0.059 Uiso 1 1 calc R C7 C 0.9295(7) 1.0215(11) 0.2437(4) 0.056(2) Uani 1 1 d . H7A H 1.0139 1.0100 0.2466 0.068 Uiso 1 1 calc R H7B H 0.9103 1.1498 0.2421 0.068 Uiso 1 1 calc R C8 C 0.8897(6) 0.9395(9) 0.3073(3) 0.0337(17) Uani 1 1 d . H8A H 0.9250 1.0033 0.3495 0.040 Uiso 1 1 calc R H8B H 0.9148 0.8137 0.3112 0.040 Uiso 1 1 calc R C9 C 0.7577(6) 0.9484(10) 0.3033(3) 0.0352(18) Uani 1 1 d . H9 H 0.7346 1.0766 0.3027 0.042 Uiso 1 1 calc R C10 C 0.6878(7) 0.8303(11) 0.1084(4) 0.060(2) Uani 1 1 d . H10A H 0.7201 0.8733 0.0665 0.072 Uiso 1 1 calc R H10B H 0.7104 0.7041 0.1156 0.072 Uiso 1 1 calc R C12 C 0.5036(7) 0.7748(12) 0.0378(4) 0.047(2) Uani 1 1 d . C13 C 0.3748(6) 0.7704(11) 0.0274(3) 0.0410(19) Uani 1 1 d . C14 C 0.3131(6) 0.8358(9) 0.0796(3) 0.0329(17) Uani 1 1 d . H14 H 0.3538 0.8848 0.1208 0.040 Uiso 1 1 calc R C15 C 0.1924 0.8307 0.0725 0.031 Uani 1 1 d . H15 H 0.1523 0.8744 0.1086 0.037 Uiso 1 1 calc R C16 C 0.1313 0.7595 0.0106 0.032 Uani 1 1 d . C17 C 0.1919 0.6938 -0.0431 0.037 Uani 1 1 d . H17 H 0.1515 0.6464 -0.0846 0.044 Uiso 1 1 calc R C18 C 0.3116(6) 0.6998(9) -0.0341(3) 0.043(2) Uani 1 1 d . H18 H 0.3518 0.6555 -0.0700 0.052 Uiso 1 1 calc R N4 N 0.7003(4) 0.8625(7) 0.2374(3) 0.0283(13) Uani 1 1 d . H4 H 0.7275 0.7464 0.2393 0.034 Uiso 1 1 calc R O11 O 0.5595(4) 0.8413(7) 0.0951(3) 0.0476(13) Uani 1 1 d . O12 O 0.5588(5) 0.7138(8) -0.0082(3) 0.0658(18) Uani 1 1 d . Cl Cl 0.73170(17) 0.4468(3) 0.23162(10) 0.0466(5) Uani 1 1 d . Br Br -0.03074(6) 0.74877(13) -0.00031(4) 0.0485(3) Uani 1 1 d . 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 0.033(4) 0.025(4) 0.031(4) -0.002(3) 0.005(3) 0.010(3) C2 0.033(4) 0.026(4) 0.041(4) 0.003(4) 0.011(3) -0.004(4) C3 0.042(5) 0.041(5) 0.044(4) -0.005(4) 0.001(4) 0.000(4) C5 0.052(6) 0.048(6) 0.062(6) 0.009(5) 0.002(4) 0.010(5) C6 0.067(6) 0.037(5) 0.045(5) 0.006(4) 0.013(4) 0.007(5) C7 0.045(6) 0.057(6) 0.067(6) -0.001(5) 0.005(5) 0.004(4) C8 0.042(5) 0.023(4) 0.035(4) -0.003(3) 0.002(3) 0.003(4) C9 0.034(4) 0.029(4) 0.043(4) 0.002(3) 0.005(3) 0.009(4) C10 0.082(7) 0.055(6) 0.043(5) 0.010(4) 0.011(4) 0.002(5) C12 0.048(5) 0.045(6) 0.049(5) -0.006(5) 0.011(4) -0.002(5) C13 0.036(4) 0.045(5) 0.042(4) -0.003(4) 0.004(3) 0.001(4) C14 0.040(4) 0.038(4) 0.020(4) -0.006(3) -0.001(3) -0.003(4) C15 0.031 0.031 0.031 0.000 0.004 0.000 C16 0.032 0.032 0.032 0.000 0.004 0.000 C17 0.037 0.037 0.037 0.000 0.005 0.000 C18 0.047(5) 0.047(6) 0.038(4) -0.006(3) 0.012(4) 0.003(4) N4 0.027(3) 0.017(3) 0.040(3) 0.006(3) 0.003(3) 0.010(3) O11 0.036(3) 0.056(3) 0.051(3) -0.002(3) 0.005(3) -0.001(3) O12 0.064(4) 0.069(5) 0.064(4) 0.000(3) 0.006(3) -0.001(3) Cl 0.0512(13) 0.0417(12) 0.0471(12) 0.0009(10) 0.0066(9) -0.0017(11) Br 0.0471(4) 0.0483(4) 0.0499(4) -0.0019(6) 0.0060(3) 0.0002(6) 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' Cl Cl 0.1484 0.1585 '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' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle C9 C1 C2 104.6(5) C3 C2 C1 99.6(5) C2 C3 N4 112.7(5) N4 C5 C10 108.8(6) N4 C5 C6 110.2(6) C10 C5 C6 109.4(7) C7 C6 C5 111.6(7) C8 C7 C6 111.0(7) C7 C8 C9 110.8(6) N4 C9 C1 101.9(5) N4 C9 C8 111.3(5) C1 C9 C8 118.7(5) O11 C10 C5 113.4(6) O12 C12 O11 119.3(7) O12 C12 C13 120.1(7) O11 C12 C13 120.6(7) C14 C13 C18 117.9(6) C14 C13 C12 120.0(6) C18 C13 C12 122.1(7) C13 C14 C15 121.7(5) C14 C15 C16 119.3(3) C17 C16 C15 120.0 C17 C16 Br 119.70(5) C15 C16 Br 120.30(5) C18 C17 C16 119.3(3) C17 C18 C13 121.8(6) C9 N4 C5 112.4(6) C9 N4 C3 101.3(5) C5 N4 C3 127.1(5) C12 O11 C10 120.5(6) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance C1 C9 1.506(9) C1 C2 1.532(8) C2 C3 1.480(8) C3 N4 1.481(8) C5 N4 1.480(9) C5 C10 1.520(10) C5 C6 1.529(9) C6 C7 1.475(9) C7 C8 1.471(9) C8 C9 1.514(8) C9 N4 1.478(8) C10 O11 1.470(8) C12 O12 1.227(8) C12 O11 1.286(8) C12 C13 1.472(9) C13 C14 1.376(9) C13 C18 1.393(9) C14 C15 1.380(7) C15 C16 1.3900 C16 C17 1.3898 C16 Br 1.8533(14) C17 C18 1.368(7) 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 C9 C1 C2 C3 30.3(7) C1 C2 C3 N4 -5.4(7) N4 C5 C6 C7 -54.6(9) C10 C5 C6 C7 -174.2(6) C5 C6 C7 C8 56.8(9) C6 C7 C8 C9 -56.9(8) C2 C1 C9 N4 -45.0(6) C2 C1 C9 C8 -167.6(6) C7 C8 C9 N4 55.6(8) C7 C8 C9 C1 173.3(6) N4 C5 C10 O11 64.2(8) C6 C5 C10 O11 -175.4(6) O12 C12 C13 C14 178.8(8) O11 C12 C13 C14 -0.8(13) O12 C12 C13 C18 -0.6(13) O11 C12 C13 C18 179.8(7) C18 C13 C14 C15 0.7(11) C12 C13 C14 C15 -178.7(6) C13 C14 C15 C16 -0.7(8) C14 C15 C16 C17 0.3(3) C14 C15 C16 Br 179.4(3) C15 C16 C17 C18 0.2(3) Br C16 C17 C18 -179.0(3) C16 C17 C18 C13 -0.2(8) C14 C13 C18 C17 -0.3(11) C12 C13 C18 C17 179.1(6) C1 C9 N4 C5 177.8(5) C8 C9 N4 C5 -54.7(7) C1 C9 N4 C3 39.4(6) C8 C9 N4 C3 166.9(6) C10 C5 N4 C9 173.7(6) C6 C5 N4 C9 53.7(8) C10 C5 N4 C3 -61.1(9) C6 C5 N4 C3 178.9(6) C2 C3 N4 C9 -21.6(7) C2 C3 N4 C5 -151.3(7) O12 C12 O11 C10 -5.3(12) C13 C12 O11 C10 174.2(7) C5 C10 O11 C12 171.2(7)