#------------------------------------------------------------------------------ #$Date: 2025-08-18 14:30:32 +0100 (Mon, 18 Aug 2025) $ #$Revision: 301775 $ #$URL: svn://www.crystallography.net/cod/cif/1/50/76/1507699.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_1507699 loop_ _publ_author_name 'Xu, Qing-Long' 'Dai, Li-Xin' 'You, Shu-Li' _publ_section_title ; Enantioselective synthesis of tetrahydroisoquinolines via iridium-catalyzed intramolecular Friedel-Crafts-type allylic alkylation of phenols. ; _journal_issue 10 _journal_name_full 'Organic letters' _journal_page_first 2579 _journal_page_last 2581 _journal_paper_doi 10.1021/ol3008793 _journal_volume 14 _journal_year 2012 _chemical_absolute_configuration ad _chemical_formula_sum 'C19 H20 Br N O2' _chemical_formula_weight 374.27 _space_group_IT_number 5 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall 'C 2y' _symmetry_space_group_name_H-M 'C 1 2 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 108.305(4) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 27.921(4) _cell_length_b 7.0957(10) _cell_length_c 8.9295(13) _cell_measurement_reflns_used 2360 _cell_measurement_temperature 133(2) _cell_measurement_theta_max 28.59 _cell_measurement_theta_min 2.40 _cell_volume 1679.6(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, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _diffrn_ambient_temperature 133(2) _diffrn_measured_fraction_theta_full 0.997 _diffrn_measured_fraction_theta_max 0.997 _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 0.0373 _diffrn_reflns_av_sigmaI/netI 0.0679 _diffrn_reflns_limit_h_max 31 _diffrn_reflns_limit_h_min -35 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_number 6131 _diffrn_reflns_theta_full 27.00 _diffrn_reflns_theta_max 27.00 _diffrn_reflns_theta_min 2.40 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 2.457 _exptl_absorpt_correction_T_max 0.8870 _exptl_absorpt_correction_T_min 0.5462 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details sadabs _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.480 _exptl_crystal_density_method 'not measured' _exptl_crystal_description prism _exptl_crystal_F_000 768 _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.05 _refine_diff_density_max 0.477 _refine_diff_density_min -0.396 _refine_diff_density_rms 0.071 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.013(12) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.076 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 210 _refine_ls_number_reflns 3273 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 1.076 _refine_ls_R_factor_all 0.0479 _refine_ls_R_factor_gt 0.0324 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0255P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0637 _refine_ls_wR_factor_ref 0.0781 _reflns_number_gt 2725 _reflns_number_total 3273 _reflns_threshold_expression >2sigma(I) _cod_data_source_file ol3008793_si_002.cif _cod_data_source_block dm11313 _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 Adding full bibliography for 1507699.cif. ; _cod_original_sg_symbol_H-M C2 _cod_database_code 1507699 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_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 Br1 Br 0.245172(14) 0.75592(6) 0.30211(4) 0.02055(10) Uani 1 1 d . C1 C 0.25076(14) 0.7444(9) 0.0955(4) 0.0179(7) Uani 1 1 d . C2 C 0.20689(12) 0.7600(9) -0.0293(4) 0.0173(7) Uani 1 1 d . C3 C 0.21039(12) 0.7534(10) -0.1831(3) 0.0180(6) Uani 1 1 d . C4 C 0.25671(13) 0.7420(11) -0.2055(4) 0.0175(8) Uani 1 1 d . H4 H 0.2589 0.7438 -0.3095 0.021 Uiso 1 1 calc R C5 C 0.30042(14) 0.7280(6) -0.0781(4) 0.0140(9) Uani 1 1 d . C6 C 0.35065(14) 0.7051(5) -0.1089(4) 0.0138(9) Uani 1 1 d . H6 H 0.3513 0.5765 -0.1541 0.017 Uiso 1 1 calc R C7 C 0.39499(14) 0.7188(5) 0.0431(4) 0.0174(10) Uani 1 1 d . H7A H 0.4259 0.6715 0.0241 0.021 Uiso 1 1 calc R H7B H 0.4006 0.8523 0.0760 0.021 Uiso 1 1 calc R C8 C 0.34511(15) 0.7031(5) 0.2154(4) 0.0199(9) Uani 1 1 d . H8A H 0.3572 0.8286 0.2600 0.024 Uiso 1 1 calc R H8B H 0.3371 0.6284 0.2981 0.024 Uiso 1 1 calc R C9 C 0.29815(15) 0.7260(6) 0.0756(4) 0.0163(9) Uani 1 1 d . C10 C 0.35796(15) 0.8466(6) -0.2258(4) 0.0188(8) Uani 1 1 d . H10 H 0.3547 0.9766 -0.2055 0.023 Uiso 1 1 calc R C11 C 0.36865(16) 0.7995(5) -0.3554(4) 0.0252(11) Uani 1 1 d . H11A H 0.3721 0.6705 -0.3787 0.030 Uiso 1 1 calc R H11B H 0.3729 0.8946 -0.4250 0.030 Uiso 1 1 calc R C12 C 0.16742(15) 0.7669(11) -0.4586(4) 0.0267(9) Uani 1 1 d . H12A H 0.1854 0.8806 -0.4733 0.040 Uiso 1 1 calc R H12B H 0.1331 0.7683 -0.5331 0.040 Uiso 1 1 calc R H12C H 0.1853 0.6551 -0.4776 0.040 Uiso 1 1 calc R C13 C 0.43054(16) 0.5874(6) 0.3072(4) 0.0236(9) Uani 1 1 d . H13A H 0.4207 0.5414 0.3980 0.028 Uiso 1 1 calc R H13B H 0.4468 0.7120 0.3355 0.028 Uiso 1 1 calc R C14 C 0.46739(16) 0.4527(6) 0.2749(5) 0.0213(9) Uani 1 1 d . C15 C 0.51090(16) 0.5147(6) 0.2429(5) 0.0235(9) Uani 1 1 d . H15 H 0.5181 0.6457 0.2453 0.028 Uiso 1 1 calc R C16 C 0.5437(2) 0.3868(7) 0.2076(6) 0.0304(12) Uani 1 1 d . H16 H 0.5725 0.4319 0.1834 0.036 Uiso 1 1 calc R C17 C 0.5351(2) 0.2002(7) 0.2073(7) 0.0385(15) Uani 1 1 d . H17 H 0.5579 0.1139 0.1840 0.046 Uiso 1 1 calc R C18 C 0.49273(19) 0.1346(7) 0.2413(7) 0.0467(14) Uani 1 1 d . H18 H 0.4864 0.0030 0.2413 0.056 Uiso 1 1 calc R C19 C 0.45969(15) 0.2609(11) 0.2752(5) 0.0372(9) Uani 1 1 d . H19 H 0.4311 0.2142 0.2992 0.045 Uiso 1 1 calc R N1 N 0.38513(12) 0.6081(4) 0.1693(3) 0.0171(7) Uani 1 1 d . O1 O 0.16095(9) 0.7769(5) -0.0061(3) 0.0188(6) Uani 1 1 d . H1 H 0.1444 0.8636 -0.0634 0.028 Uiso 1 1 calc R O2 O 0.16520(9) 0.7621(7) -0.3013(2) 0.0213(5) 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 Br1 0.02606(19) 0.02332(17) 0.01576(15) 0.0011(3) 0.01155(12) 0.0028(3) C1 0.0309(19) 0.0102(16) 0.0177(15) 0.004(3) 0.0149(14) 0.005(3) C2 0.0226(17) 0.0129(15) 0.0193(15) 0.002(3) 0.0108(13) 0.006(3) C3 0.0231(18) 0.0124(14) 0.0181(15) 0.000(3) 0.0057(13) 0.001(3) C4 0.0245(19) 0.015(2) 0.0151(14) -0.002(3) 0.0096(14) -0.003(3) C5 0.0194(18) 0.007(2) 0.0174(15) -0.0015(16) 0.0091(13) 0.0009(17) C6 0.0132(18) 0.012(2) 0.0154(17) 0.0000(13) 0.0037(14) -0.0016(14) C7 0.0140(18) 0.018(3) 0.0196(17) -0.0011(16) 0.0042(14) -0.0026(15) C8 0.024(2) 0.022(2) 0.0158(17) -0.0023(14) 0.0090(16) 0.0003(15) C9 0.0267(19) 0.005(2) 0.0169(15) -0.0005(16) 0.0070(14) 0.0006(16) C10 0.014(2) 0.021(2) 0.021(2) 0.0058(16) 0.0049(17) 0.0057(16) C11 0.033(2) 0.024(3) 0.0208(19) 0.0040(16) 0.0109(17) 0.0049(17) C12 0.029(2) 0.034(2) 0.0158(16) -0.004(3) 0.0051(14) 0.003(3) C13 0.022(2) 0.029(2) 0.017(2) 0.0006(17) 0.0023(17) -0.0018(19) C14 0.011(2) 0.031(2) 0.017(2) 0.0053(17) -0.0022(16) -0.0026(18) C15 0.012(2) 0.025(2) 0.028(2) 0.0061(19) -0.0028(18) -0.0017(17) C16 0.019(3) 0.038(3) 0.034(3) 0.007(2) 0.009(2) 0.005(2) C17 0.017(2) 0.041(4) 0.049(3) -0.002(2) -0.002(2) 0.014(2) C18 0.022(3) 0.027(3) 0.080(4) -0.001(3) 0.001(3) -0.003(2) C19 0.025(2) 0.028(2) 0.058(2) 0.004(4) 0.0130(19) 0.000(4) N1 0.0168(18) 0.0211(16) 0.0135(16) 0.0007(13) 0.0048(14) -0.0019(14) O1 0.0129(12) 0.0209(18) 0.0248(12) 0.0063(15) 0.0093(10) 0.0064(14) O2 0.0172(12) 0.0311(14) 0.0154(10) 0.003(2) 0.0049(9) 0.006(2) 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' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle C2 C1 C9 122.9(3) C2 C1 Br1 117.3(2) C9 C1 Br1 119.8(3) O1 C2 C1 121.5(3) O1 C2 C3 120.4(3) C1 C2 C3 118.0(3) O2 C3 C4 125.0(3) O2 C3 C2 114.9(3) C4 C3 C2 120.1(3) C3 C4 C5 120.8(3) C3 C4 H4 119.6 C5 C4 H4 119.6 C4 C5 C9 120.5(3) C4 C5 C6 118.9(3) C9 C5 C6 120.5(3) C10 C6 C5 112.8(3) C10 C6 C7 109.0(3) C5 C6 C7 111.7(3) C10 C6 H6 107.7 C5 C6 H6 107.7 C7 C6 H6 107.7 N1 C7 C6 110.7(3) N1 C7 H7A 109.5 C6 C7 H7A 109.5 N1 C7 H7B 109.5 C6 C7 H7B 109.5 H7A C7 H7B 108.1 N1 C8 C9 110.9(3) N1 C8 H8A 109.5 C9 C8 H8A 109.5 N1 C8 H8B 109.5 C9 C8 H8B 109.5 H8A C8 H8B 108.0 C5 C9 C1 117.6(3) C5 C9 C8 121.3(3) C1 C9 C8 121.2(3) C11 C10 C6 123.6(4) C11 C10 H10 118.2 C6 C10 H10 118.2 C10 C11 H11A 120.0 C10 C11 H11B 120.0 H11A C11 H11B 120.0 O2 C12 H12A 109.5 O2 C12 H12B 109.5 H12A C12 H12B 109.5 O2 C12 H12C 109.5 H12A C12 H12C 109.5 H12B C12 H12C 109.5 N1 C13 C14 111.5(3) N1 C13 H13A 109.3 C14 C13 H13A 109.3 N1 C13 H13B 109.3 C14 C13 H13B 109.3 H13A C13 H13B 108.0 C19 C14 C15 117.1(4) C19 C14 C13 120.9(4) C15 C14 C13 122.0(4) C16 C15 C14 121.0(4) C16 C15 H15 119.5 C14 C15 H15 119.5 C17 C16 C15 120.8(5) C17 C16 H16 119.6 C15 C16 H16 119.6 C16 C17 C18 119.5(5) C16 C17 H17 120.3 C18 C17 H17 120.3 C19 C18 C17 120.1(5) C19 C18 H18 120.0 C17 C18 H18 120.0 C14 C19 C18 121.6(5) C14 C19 H19 119.2 C18 C19 H19 119.2 C7 N1 C8 108.2(3) C7 N1 C13 112.1(3) C8 N1 C13 110.0(3) C2 O1 H1 109.5 C3 O2 C12 116.5(3) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance Br1 C1 1.901(3) C1 C2 1.377(4) C1 C9 1.395(5) C2 O1 1.367(4) C2 C3 1.408(4) C3 O2 1.369(4) C3 C4 1.371(5) C4 C5 1.386(5) C4 H4 0.9500 C5 C9 1.394(4) C5 C6 1.520(5) C6 C10 1.508(5) C6 C7 1.526(5) C6 H6 1.0000 C7 N1 1.469(4) C7 H7A 0.9900 C7 H7B 0.9900 C8 N1 1.470(5) C8 C9 1.508(5) C8 H8A 0.9900 C8 H8B 0.9900 C10 C11 1.325(5) C10 H10 0.9500 C11 H11A 0.9500 C11 H11B 0.9500 C12 O2 1.426(4) C12 H12A 0.9800 C12 H12B 0.9800 C12 H12C 0.9800 C13 N1 1.471(5) C13 C14 1.497(6) C13 H13A 0.9900 C13 H13B 0.9900 C14 C19 1.378(9) C14 C15 1.403(6) C15 C16 1.395(7) C15 H15 0.9500 C16 C17 1.345(8) C16 H16 0.9500 C17 C18 1.392(8) C17 H17 0.9500 C18 C19 1.386(8) C18 H18 0.9500 C19 H19 0.9500 O1 H1 0.8400 loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1 H1 N1 0.84 2.02 2.850(5) 168.1 4 loop_ _cod_related_entry_id _cod_related_entry_code _cod_related_entry_database 1 30651894 ChemSpider 2 135068220 PubChem