#------------------------------------------------------------------------------ #$Date: 2017-10-13 02:32:00 +0300 (Fri, 13 Oct 2017) $ #$Revision: 201954 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/50/21/1502148.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_1502148 loop_ _publ_author_name 'Qian, Bo' 'Xie, Pan' 'Xie, Yinjun' 'Huang, Hanmin' _publ_section_title ; Iron-catalyzed direct alkenylation of 2-substituted azaarenes with N-sulfonyl aldimines via C-H bond activation. ; _journal_issue 10 _journal_name_full 'Organic letters' _journal_page_first 2580 _journal_page_last 2583 _journal_paper_doi 10.1021/ol200684b _journal_volume 13 _journal_year 2011 _chemical_formula_sum 'C18 H15 N O' _chemical_formula_weight 261.31 _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 94.025(19) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 10.424(19) _cell_length_b 16.830(3) _cell_length_c 7.934(15) _cell_measurement_reflns_used 1346 _cell_measurement_temperature 296(2) _cell_measurement_theta_max 22.28 _cell_measurement_theta_min 2.30 _cell_volume 1388(4) _computing_cell_refinement 'Bruker SAINT' _computing_data_collection 'Bruker APEX2' _computing_data_reduction 'Bruker SAINT' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _diffrn_ambient_temperature 296(2) _diffrn_measured_fraction_theta_full 0.994 _diffrn_measured_fraction_theta_max 0.994 _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _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 0.0504 _diffrn_reflns_av_sigmaI/netI 0.0598 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_number 7755 _diffrn_reflns_theta_full 25.49 _diffrn_reflns_theta_max 25.49 _diffrn_reflns_theta_min 2.30 _exptl_absorpt_coefficient_mu 0.077 _exptl_absorpt_correction_T_max 0.9757 _exptl_absorpt_correction_T_min 0.9734 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details sadabs _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.250 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 552 _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.33 _exptl_crystal_size_min 0.32 _refine_diff_density_max 0.132 _refine_diff_density_min -0.113 _refine_diff_density_rms 0.032 _refine_ls_extinction_coef 0.043(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method SHELXL _refine_ls_goodness_of_fit_ref 1.013 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 183 _refine_ls_number_reflns 2571 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.013 _refine_ls_R_factor_all 0.0895 _refine_ls_R_factor_gt 0.0468 _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^)+(0.0448P)^2^+0.1049P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1035 _refine_ls_wR_factor_ref 0.1246 _reflns_number_gt 1539 _reflns_number_total 2571 _reflns_threshold_expression >2sigma(I) _cod_data_source_file ol200684b_si_001.cif _cod_data_source_block p21c _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic' according to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. Automatic conversion script Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana ; _cod_original_sg_symbol_H-M P2(1)/c _cod_database_code 1502148 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 0.60530(17) 0.91114(11) 0.3903(2) 0.0487(5) Uani 1 1 d . C2 C 0.5745(2) 0.98399(12) 0.3043(2) 0.0541(5) Uani 1 1 d . C3 C 0.6674(2) 1.03987(13) 0.2867(3) 0.0703(6) Uani 1 1 d . H3 H 0.6467 1.0876 0.2323 0.084 Uiso 1 1 calc R C4 C 0.7935(3) 1.02560(17) 0.3503(3) 0.0862(8) Uani 1 1 d . H4 H 0.8558 1.0643 0.3375 0.103 Uiso 1 1 calc R C5 C 0.8274(2) 0.95711(17) 0.4298(3) 0.0804(8) Uani 1 1 d . H5 H 0.9123 0.9488 0.4699 0.096 Uiso 1 1 calc R C6 C 0.73386(18) 0.89802(13) 0.4520(3) 0.0596(6) Uani 1 1 d . C7 C 0.7596(2) 0.82512(15) 0.5342(3) 0.0693(7) Uani 1 1 d . H7 H 0.8432 0.8130 0.5743 0.083 Uiso 1 1 calc R C8 C 0.66393(19) 0.77246(13) 0.5557(3) 0.0625(6) Uani 1 1 d . H8 H 0.6815 0.7244 0.6105 0.075 Uiso 1 1 calc R C9 C 0.53730(17) 0.79121(11) 0.4941(2) 0.0486(5) Uani 1 1 d . C10 C 0.43227(19) 0.73678(11) 0.5248(2) 0.0513(5) Uani 1 1 d . H10 H 0.4524 0.6909 0.5864 0.062 Uiso 1 1 calc R C11 C 0.31085(18) 0.74798(11) 0.4713(2) 0.0533(5) Uani 1 1 d . H11 H 0.2930 0.7937 0.4079 0.064 Uiso 1 1 calc R C12 C 0.20113(18) 0.69677(11) 0.5004(2) 0.0496(5) Uani 1 1 d . C13 C 0.21003(19) 0.63090(11) 0.6056(2) 0.0551(5) Uani 1 1 d . H13 H 0.2893 0.6169 0.6585 0.066 Uiso 1 1 calc R C14 C 0.1031(2) 0.58601(12) 0.6328(3) 0.0678(6) Uani 1 1 d . H14 H 0.1106 0.5427 0.7056 0.081 Uiso 1 1 calc R C15 C -0.0144(2) 0.60430(14) 0.5539(3) 0.0722(7) Uani 1 1 d . H15 H -0.0861 0.5733 0.5719 0.087 Uiso 1 1 calc R C16 C -0.0252(2) 0.66871(14) 0.4483(3) 0.0717(7) Uani 1 1 d . H16 H -0.1045 0.6816 0.3943 0.086 Uiso 1 1 calc R C17 C 0.08107(19) 0.71444(12) 0.4217(3) 0.0628(6) Uani 1 1 d . H17 H 0.0724 0.7580 0.3498 0.075 Uiso 1 1 calc R C18 C 0.4133(2) 1.06118(11) 0.1534(3) 0.0731(7) Uani 1 1 d . H18A H 0.4280 1.1067 0.2251 0.110 Uiso 1 1 calc R H18B H 0.3237 1.0582 0.1167 0.110 Uiso 1 1 calc R H18C H 0.4632 1.0660 0.0568 0.110 Uiso 1 1 calc R N1 N 0.50960(13) 0.85814(9) 0.41118(19) 0.0470(4) Uani 1 1 d . O1 O 0.45013(13) 0.99116(7) 0.24453(17) 0.0626(4) 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 0.0509(12) 0.0559(12) 0.0394(11) -0.0136(9) 0.0043(9) -0.0052(10) C2 0.0618(13) 0.0586(13) 0.0425(12) -0.0100(10) 0.0078(9) -0.0114(11) C3 0.0794(16) 0.0695(15) 0.0631(15) -0.0063(11) 0.0123(12) -0.0229(12) C4 0.0767(18) 0.0924(19) 0.091(2) -0.0123(16) 0.0165(15) -0.0359(15) C5 0.0546(14) 0.107(2) 0.0792(19) -0.0187(16) 0.0054(12) -0.0191(14) C6 0.0519(12) 0.0737(15) 0.0533(14) -0.0165(11) 0.0046(10) -0.0058(11) C7 0.0499(13) 0.0906(18) 0.0660(16) -0.0167(13) -0.0064(11) 0.0100(12) C8 0.0610(13) 0.0641(14) 0.0609(15) -0.0037(11) -0.0075(11) 0.0119(11) C9 0.0530(12) 0.0507(12) 0.0415(12) -0.0065(9) -0.0010(9) 0.0047(9) C10 0.0630(12) 0.0441(11) 0.0459(12) 0.0008(9) -0.0028(10) 0.0045(10) C11 0.0611(13) 0.0484(11) 0.0500(13) 0.0071(9) 0.0014(10) 0.0035(10) C12 0.0594(12) 0.0450(11) 0.0441(12) 0.0000(9) 0.0018(9) 0.0035(9) C13 0.0641(13) 0.0469(12) 0.0537(13) -0.0012(10) -0.0011(10) 0.0027(10) C14 0.0865(16) 0.0526(13) 0.0643(15) 0.0047(11) 0.0057(12) -0.0080(12) C15 0.0733(15) 0.0692(15) 0.0742(17) -0.0041(13) 0.0059(13) -0.0158(12) C16 0.0579(13) 0.0805(16) 0.0761(18) -0.0007(13) 0.0001(12) -0.0002(12) C17 0.0608(13) 0.0646(14) 0.0626(15) 0.0108(11) 0.0003(11) 0.0048(11) C18 0.1038(17) 0.0494(13) 0.0659(15) 0.0041(11) 0.0038(13) 0.0037(12) N1 0.0504(9) 0.0494(9) 0.0411(9) -0.0061(8) 0.0021(7) -0.0024(8) O1 0.0702(10) 0.0538(9) 0.0626(10) 0.0088(7) -0.0029(7) -0.0061(7) 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' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle N1 C1 C6 122.9(2) N1 C1 C2 118.67(19) C6 C1 C2 118.45(18) O1 C2 C3 124.9(2) O1 C2 C1 114.92(17) C3 C2 C1 120.2(2) C2 C3 C4 120.2(3) C2 C3 H3 119.9 C4 C3 H3 119.9 C5 C4 C3 121.7(2) C5 C4 H4 119.2 C3 C4 H4 119.2 C4 C5 C6 120.0(2) C4 C5 H5 120.0 C6 C5 H5 120.0 C7 C6 C1 116.29(19) C7 C6 C5 124.2(2) C1 C6 C5 119.6(2) C8 C7 C6 120.8(2) C8 C7 H7 119.6 C6 C7 H7 119.6 C7 C8 C9 119.3(2) C7 C8 H8 120.3 C9 C8 H8 120.3 N1 C9 C8 121.85(18) N1 C9 C10 118.38(19) C8 C9 C10 119.8(2) C11 C10 C9 124.8(2) C11 C10 H10 117.6 C9 C10 H10 117.6 C10 C11 C12 127.4(2) C10 C11 H11 116.3 C12 C11 H11 116.3 C13 C12 C17 117.45(19) C13 C12 C11 123.06(19) C17 C12 C11 119.5(2) C14 C13 C12 120.8(2) C14 C13 H13 119.6 C12 C13 H13 119.6 C15 C14 C13 120.9(2) C15 C14 H14 119.6 C13 C14 H14 119.6 C16 C15 C14 119.3(2) C16 C15 H15 120.4 C14 C15 H15 120.4 C15 C16 C17 120.2(2) C15 C16 H16 119.9 C17 C16 H16 119.9 C16 C17 C12 121.3(2) C16 C17 H17 119.3 C12 C17 H17 119.3 O1 C18 H18A 109.5 O1 C18 H18B 109.5 H18A C18 H18B 109.5 O1 C18 H18C 109.5 H18A C18 H18C 109.5 H18B C18 H18C 109.5 C9 N1 C1 118.85(18) C2 O1 C18 118.03(16) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance C1 N1 1.357(3) C1 C6 1.412(3) C1 C2 1.429(3) C2 O1 1.354(3) C2 C3 1.364(3) C3 C4 1.395(4) C3 H3 0.9300 C4 C5 1.349(4) C4 H4 0.9300 C5 C6 1.412(3) C5 H5 0.9300 C6 C7 1.406(4) C7 C8 1.353(3) C7 H7 0.9300 C8 C9 1.411(3) C8 H8 0.9300 C9 N1 1.326(3) C9 C10 1.461(3) C10 C11 1.320(3) C10 H10 0.9300 C11 C12 1.463(3) C11 H11 0.9300 C12 C13 1.387(3) C12 C17 1.391(3) C13 C14 1.376(3) C13 H13 0.9300 C14 C15 1.371(3) C14 H14 0.9300 C15 C16 1.370(4) C15 H15 0.9300 C16 C17 1.377(3) C16 H16 0.9300 C17 H17 0.9300 C18 O1 1.421(3) C18 H18A 0.9600 C18 H18B 0.9600 C18 H18C 0.9600 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 N1 C1 C2 O1 -2.8(2) C6 C1 C2 O1 178.16(15) N1 C1 C2 C3 177.51(17) C6 C1 C2 C3 -1.6(3) O1 C2 C3 C4 -178.64(19) C1 C2 C3 C4 1.1(3) C2 C3 C4 C5 0.1(4) C3 C4 C5 C6 -0.7(4) N1 C1 C6 C7 1.6(3) C2 C1 C6 C7 -179.38(17) N1 C1 C6 C5 -178.07(18) C2 C1 C6 C5 1.0(3) C4 C5 C6 C7 -179.5(2) C4 C5 C6 C1 0.1(3) C1 C6 C7 C8 -1.9(3) C5 C6 C7 C8 177.8(2) C6 C7 C8 C9 0.2(3) C7 C8 C9 N1 2.0(3) C7 C8 C9 C10 -176.65(19) N1 C9 C10 C11 2.1(3) C8 C9 C10 C11 -179.16(18) C9 C10 C11 C12 -178.70(18) C10 C11 C12 C13 6.4(3) C10 C11 C12 C17 -174.41(19) C17 C12 C13 C14 -1.2(3) C11 C12 C13 C14 178.01(18) C12 C13 C14 C15 1.3(3) C13 C14 C15 C16 -0.7(3) C14 C15 C16 C17 0.0(3) C15 C16 C17 C12 0.1(3) C13 C12 C17 C16 0.5(3) C11 C12 C17 C16 -178.71(19) C8 C9 N1 C1 -2.3(3) C10 C9 N1 C1 176.38(16) C6 C1 N1 C9 0.5(3) C2 C1 N1 C9 -178.56(16) C3 C2 O1 C18 1.4(3) C1 C2 O1 C18 -178.27(16) loop_ _cod_related_entry_id _cod_related_entry_code _cod_related_entry_database 1 28419203 ChemSpider