#------------------------------------------------------------------------------ #$Date: 2016-02-14 06:40:26 +0200 (Sun, 14 Feb 2016) $ #$Revision: 176432 $ #$URL: file:///home/coder/svn-repositories/cod/cif/4/06/66/4066669.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_4066669 loop_ _publ_author_name 'Eloi, Antoine' 'Rose-Munch, Fran\,coise' 'Rose, Eric' 'Pille, Ariane' 'Lesot, Philippe' 'Herson, Patrick' _publ_section_title ; Cationic Planar Chiral (\h6-Arene)Mn(CO)3+Complexes: Resolution, NMR Study in Chiral-Oriented Solvents, and Applications to the Enantioselective Synthesis of 4-Substituted Cyclohexenones and (\h6-Phosphinoarene)Mn(CO)3+Complexes ; _journal_issue 17 _journal_name_full Organometallics _journal_page_first 3876 _journal_paper_doi 10.1021/om100564v _journal_volume 29 _journal_year 2010 _chemical_absolute_configuration ad _chemical_formula_moiety 'C10 H12 Br1 N1 O1' _chemical_formula_sum 'C10 H12 Br N O' _chemical_formula_weight 242.12 _space_group_IT_number 19 _symmetry_cell_setting orthorhombic _symmetry_space_group_name_Hall 'P 2ac 2ab' _symmetry_space_group_name_H-M 'P 21 21 21' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 7.5481(4) _cell_length_b 11.1754(7) _cell_length_c 12.3578(5) _cell_measurement_reflns_used 120 _cell_measurement_temperature 200 _cell_measurement_theta_max 20 _cell_measurement_theta_min 2 _cell_volume 1042.42(10) _computing_cell_refinement 'Dirax/lsq (Duisenberg & Schreurs, 1989-2000)' _computing_data_collection 'COLLECT (Nonius, 2001).' _computing_data_reduction 'EvalCCD (Duisenberg & Schreurs 1990-2000)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_structure_solution 'SHELXS 86 (Sheldrick, 1986)' _diffrn_ambient_temperature 200 _diffrn_measured_fraction_theta_full 0.997 _diffrn_measured_fraction_theta_max 0.997 _diffrn_measurement_device 'Nonius KappaCCD' _diffrn_measurement_device_type Area _diffrn_measurement_method '\f & \w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.000 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_number 9885 _diffrn_reflns_theta_full 29.989 _diffrn_reflns_theta_max 29.989 _diffrn_reflns_theta_min 3.162 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 3.904 _exptl_absorpt_correction_T_max 0.50 _exptl_absorpt_correction_T_min 0.46 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS (Siemens, 1996)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.543 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 488 _exptl_crystal_size_max 0.240 _exptl_crystal_size_mid 0.220 _exptl_crystal_size_min 0.180 _refine_diff_density_max 0.65 _refine_diff_density_min -0.77 _refine_ls_abs_structure_details 'Flack (1983), 0 Friedel-pairs' _refine_ls_abs_structure_Flack 0.135(16) _refine_ls_extinction_coef 82 _refine_ls_extinction_method 'Larson (1970), Equation 22' _refine_ls_goodness_of_fit_ref 0.9119 _refine_ls_hydrogen_treatment refU _refine_ls_matrix_type full _refine_ls_number_parameters 120 _refine_ls_number_reflns 3016 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0512 _refine_ls_R_factor_gt 0.0377 _refine_ls_shift/su_max 0.0006135 _refine_ls_shift/su_mean 0.0842424 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details ; Method= Modified Sheldrick w=1/[\s^2^(F^2^) + ( 0.06P)^2^ + 1.04P] ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 ; _refine_ls_weighting_scheme calc _refine_ls_wR_factor_all 0.1002 _refine_ls_wR_factor_gt 0.0889 _refine_ls_wR_factor_ref 0.1002 _reflns_limit_h_max 10 _reflns_limit_h_min -10 _reflns_limit_k_max 15 _reflns_limit_k_min 0 _reflns_limit_l_max 17 _reflns_limit_l_min 0 _reflns_number_gt 2520 _reflns_number_total 3018 _reflns_threshold_expression I>2.0\s(I) _oxford_refine_ls_r_factor_ref 0.0512 _oxford_reflns_number_all 3016 _oxford_reflns_threshold_expression_ref I>-3.0\s(I) _cod_data_source_file om100564v_si_002.cif _cod_data_source_block 1 _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic' 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_Hall '-P 2ac 2ac' _cod_original_sg_symbol_H-M 'P 21 21 21 ' _cod_original_formula_sum 'C10 H12 Br1 N1 O1' _cod_database_code 4066669 loop_ _symmetry_equiv_pos_as_xyz x,y,z x+1/2,-y+1/2,-z -x,y+1/2,-z+1/2 -x+1/2,-y,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_occupancy _atom_site_adp_type Br1 Br 0.45915(5) 0.69977(3) 0.49082(3) 0.0450 1.0000 Uani C1 C 0.1233(4) 0.6270(3) 0.7491(2) 0.0295 1.0000 Uani C2 C 0.2452(4) 0.6809(2) 0.6710(2) 0.0222 1.0000 Uani C3 C 0.3143(4) 0.6188(3) 0.5909(2) 0.0211 1.0000 Uani C4 C 0.2861(4) 0.4865(3) 0.5745(2) 0.0199 1.0000 Uani C5 C 0.0949(4) 0.4613(3) 0.6105(2) 0.0270 1.0000 Uani C6 C 0.0571(5) 0.5037(3) 0.7255(2) 0.0307 1.0000 Uani C7 C 0.4329(4) 0.4079(3) 0.6287(2) 0.0259 1.0000 Uani C8 C 0.6122(5) 0.4260(4) 0.5737(3) 0.0402 1.0000 Uani C9 C 0.3815(6) 0.2751(3) 0.6223(3) 0.0440 1.0000 Uani C10 C 0.4560(5) 0.4425(3) 0.7436(3) 0.0315 1.0000 Uani N1 N 0.4810(6) 0.4688(3) 0.8308(2) 0.0504 1.0000 Uani O1 O 0.0787(4) 0.6823(3) 0.8297(2) 0.0466 1.0000 Uani H21 H 0.2754 0.7630 0.6784 0.037(3) 1.0000 Uiso H41 H 0.2915 0.4719 0.4989 0.037(3) 1.0000 Uiso H51 H 0.0164 0.5013 0.5625 0.037(3) 1.0000 Uiso H52 H 0.0745 0.3775 0.6069 0.037(3) 1.0000 Uiso H61 H 0.1122 0.4498 0.7745 0.037(3) 1.0000 Uiso H62 H -0.0674 0.5026 0.7365 0.037(3) 1.0000 Uiso H81 H 0.6987 0.3773 0.6081 0.037(3) 1.0000 Uiso H82 H 0.6460 0.5077 0.5792 0.037(3) 1.0000 Uiso H83 H 0.6034 0.4043 0.4995 0.037(3) 1.0000 Uiso H91 H 0.4712 0.2280 0.6554 0.037(3) 1.0000 Uiso H92 H 0.2724 0.2629 0.6590 0.037(3) 1.0000 Uiso H93 H 0.3691 0.2523 0.5487 0.037(3) 1.0000 Uiso 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 0.0532(2) 0.0425(2) 0.0394(2) 0.00340(16) 0.01741(17) -0.01694(15) C1 0.0251(16) 0.0432(18) 0.0201(13) 0.0002(13) 0.0009(11) 0.0072(14) C2 0.0286(15) 0.0156(13) 0.0223(12) 0.0019(10) -0.0037(10) 0.0015(10) C3 0.0211(13) 0.0255(13) 0.0168(11) 0.0037(10) -0.0002(10) -0.0075(11) C4 0.0205(14) 0.0223(13) 0.0168(11) -0.0024(10) -0.0006(10) 0.0006(10) C5 0.0248(15) 0.0317(15) 0.0246(14) 0.0011(12) -0.0017(11) -0.0041(12) C6 0.0261(16) 0.0424(18) 0.0236(13) 0.0049(12) 0.0080(13) -0.0039(14) C7 0.0276(16) 0.0257(14) 0.0244(13) -0.0074(11) -0.0047(12) 0.0058(12) C8 0.0263(16) 0.053(2) 0.0417(19) -0.0111(17) -0.0013(14) 0.0107(16) C9 0.056(2) 0.0253(17) 0.051(2) -0.0011(14) -0.0159(18) 0.0093(16) C10 0.0357(18) 0.0261(14) 0.0327(15) 0.0002(12) -0.0064(16) 0.0149(15) N1 0.077(3) 0.0488(18) 0.0256(14) -0.0054(12) -0.0177(16) 0.0163(18) O1 0.0579(19) 0.0509(16) 0.0308(11) -0.0071(11) 0.0156(12) 0.0132(14) loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4' Br -0.2901 2.4595 17.1789 2.1723 5.2358 16.5796 5.6377 0.2609 3.9851 41.4328 2.9557 'International Tables Vol C 4.2.6.8 and 6.1.1.4' N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4' O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 'International Tables Vol C 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 _geom_angle_publ_flag C2 C1 C6 117.4(3) yes C2 C1 O1 120.3(3) yes C6 C1 O1 122.3(3) yes C1 C2 C3 121.9(3) yes C1 C2 H21 119.1 no C3 C2 H21 119.1 no Br1 C3 C2 118.1(2) yes Br1 C3 C4 117.8(2) yes C2 C3 C4 124.2(3) yes C3 C4 C5 105.9(2) yes C3 C4 C7 113.2(2) yes C5 C4 C7 116.0(2) yes C3 C4 H41 107.1 no C5 C4 H41 107.1 no C7 C4 H41 107.1 no C4 C5 C6 112.9(3) yes C4 C5 H51 108.6 no C6 C5 H51 108.6 no C4 C5 H52 108.6 no C6 C5 H52 108.6 no H51 C5 H52 109.5 no C5 C6 C1 114.0(3) yes C5 C6 H61 108.3 no C1 C6 H61 108.3 no C5 C6 H62 108.3 no C1 C6 H62 108.3 no H61 C6 H62 109.5 no C4 C7 C8 111.2(3) yes C4 C7 C9 110.0(3) yes C8 C7 C9 109.2(3) yes C4 C7 C10 110.3(2) yes C8 C7 C10 106.7(3) yes C9 C7 C10 109.3(3) yes C7 C8 H81 109.5 no C7 C8 H82 109.5 no H81 C8 H82 109.5 no C7 C8 H83 109.5 no H81 C8 H83 109.5 no H82 C8 H83 109.5 no C7 C9 H91 109.5 no C7 C9 H92 109.5 no H91 C9 H92 109.5 no C7 C9 H93 109.5 no H91 C9 H93 109.5 no H92 C9 H93 109.5 no C7 C10 N1 177.2(4) yes loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag Br1 C3 1.883(3) yes C1 C2 1.463(4) yes C1 C6 1.494(5) yes C1 O1 1.219(4) yes C2 C3 1.318(4) yes C2 H21 0.950 no C3 C4 1.507(4) yes C4 C5 1.536(4) yes C4 C7 1.565(4) yes C4 H41 0.950 no C5 C6 1.525(4) yes C5 H51 0.950 no C5 H52 0.950 no C6 H61 0.950 no C6 H62 0.950 no C7 C8 1.528(5) yes C7 C9 1.535(4) yes C7 C10 1.482(4) yes C8 H81 0.950 no C8 H82 0.950 no C8 H83 0.950 no C9 H91 0.950 no C9 H92 0.950 no C9 H93 0.950 no C10 N1 1.133(4) yes