#------------------------------------------------------------------------------ #$Date: 2015-01-23 14:30:19 +0200 (Fri, 23 Jan 2015) $ #$Revision: 130086 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/50/39/1503911.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_1503911 loop_ _publ_author_name 'Donohoe, Timothy J.' 'Callens, Cedric K. A.' 'Thompson, Amber L.' _publ_section_title ; Tethered aminohydroxylation (TA) reaction of amides. ; _journal_issue 11 _journal_name_full 'Organic letters' _journal_page_first 2305 _journal_page_last 2307 _journal_paper_doi 10.1021/ol900631y _journal_volume 11 _journal_year 2009 _chemical_compound_source 'org. synthesis' _chemical_formula_moiety 'C11 H13 N1 O2' _chemical_formula_sum 'C11 H13 N O2' _chemical_formula_weight 191.23 _chemical_melting_point ? _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 _audit_creation_date 08-06-23 _audit_creation_method CRYSTALS_ver_12.86 _cell_angle_alpha 90 _cell_angle_beta 100.9990(9) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 18.0508(4) _cell_length_b 6.27090(10) _cell_length_c 9.1222(2) _cell_measurement_reflns_used 2487 _cell_measurement_temperature 150 _cell_measurement_theta_max 27 _cell_measurement_theta_min 5 _cell_volume 1013.62(4) _computing_cell_refinement 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_data_collection 'COLLECT (Nonius, 1997-2001).' _computing_data_reduction 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _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 'SIR92 (Altomare et al., 1994)' _diffrn_ambient_temperature 150 _diffrn_measured_fraction_theta_full 0.991 _diffrn_measured_fraction_theta_max 0.991 _diffrn_measurement_device 'Nonius KappaCCD' _diffrn_measurement_device_type Area _diffrn_measurement_method \w _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.037 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_h_min -23 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_number 16667 _diffrn_reflns_theta_full 26.949 _diffrn_reflns_theta_max 27.499 _diffrn_reflns_theta_min 5.163 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.087 _exptl_absorpt_correction_T_max 0.98 _exptl_absorpt_correction_T_min 0.89 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.253 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 408 _exptl_crystal_size_max 0.48 _exptl_crystal_size_mid 0.38 _exptl_crystal_size_min 0.20 _refine_diff_density_max 0.29 _refine_diff_density_min -0.27 _refine_ls_extinction_method None _refine_ls_goodness_of_fit_ref 0.9412 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 127 _refine_ls_number_reflns 2305 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0581 _refine_ls_R_factor_gt 0.0429 _refine_ls_shift/su_max 0.000114 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details ; Method= Modified Sheldrick w=1/[\s^2^(F^2^) + ( 0.05P)^2^ + 0.38P] ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 ; _refine_ls_weighting_scheme calc _refine_ls_wR_factor_all 0.1061 _refine_ls_wR_factor_gt 0.0986 _refine_ls_wR_factor_ref 0.1061 _reflns_limit_h_max 23 _reflns_limit_h_min 0 _reflns_limit_k_max 0 _reflns_limit_k_min -8 _reflns_limit_l_max 11 _reflns_limit_l_min -11 _reflns_number_gt 1830 _reflns_number_total 2305 _reflns_threshold_expression I>2.0\s(I) _oxford_diffrn_Wilson_B_factor 2.71 _oxford_diffrn_Wilson_scale 0.98 _oxford_refine_ls_r_factor_ref 0.0581 _oxford_refine_ls_scale 1.059(5) _oxford_reflns_number_all 2305 _oxford_reflns_threshold_expression_ref I>-3.0\s(I) _oxford_structure_analysis_title 0020608 _[local]_cod_data_source_file ol900631y_si_002.cif _[local]_cod_data_source_block Compound_12 _[local]_cod_cif_authors_sg_H-M 'P 1 21/c 1 ' _[local]_cod_chemical_formula_sum_orig 'C11 H13 N1 O2' _cod_depositor_comments ; The following automatic conversions were performed: '_chemical_melting_point' value 'not measured' was changed to '?' - the value is undefined or not given. '_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic' according to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26. Automatic conversion script Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana The following automatic conversions were performed: '_exptl_crystal_density_meas' value 'not measured' was changed to '?' - the value is perceived as not measured. Automatic conversion script Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas ; _cod_database_code 1503911 loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z -x,y+1/2,-z+1/2 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_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn O1 O -0.02856(5) 0.35186(16) 0.13651(10) 0.0395 1.0000 Uani . C2 C 0.04135(7) 0.3432(2) 0.15193(13) 0.0298 1.0000 Uani . N3 N 0.08878(5) 0.48892(17) 0.22187(11) 0.0285 1.0000 Uani . C4 C 0.16872(6) 0.44050(19) 0.23318(13) 0.0266 1.0000 Uani . C5 C 0.20763(7) 0.6022(2) 0.14725(14) 0.0318 1.0000 Uani . O6 O 0.17852(5) 0.59266(19) -0.00800(10) 0.0495 1.0000 Uani . C7 C 0.29166(7) 0.5614(2) 0.17574(14) 0.0310 1.0000 Uani . C8 C 0.32658(7) 0.4528(2) 0.07478(15) 0.0362 1.0000 Uani . C9 C 0.40392(7) 0.4145(2) 0.10778(17) 0.0435 1.0000 Uani . C10 C 0.44654(8) 0.4825(3) 0.24111(18) 0.0480 1.0000 Uani . C11 C 0.41206(8) 0.5895(3) 0.34249(18) 0.0488 1.0000 Uani . C12 C 0.33527(8) 0.6277(2) 0.31005(16) 0.0414 1.0000 Uani . C13 C 0.16739(7) 0.2105(2) 0.17406(16) 0.0377 1.0000 Uani . C14 C 0.08643(7) 0.1685(2) 0.09768(16) 0.0389 1.0000 Uani . H41 H 0.1947 0.4461 0.3389 0.0326 1.0000 Uiso R H51 H 0.1980 0.7482 0.1860 0.0379 1.0000 Uiso R H81 H 0.2972 0.4082 -0.0185 0.0438 1.0000 Uiso R H91 H 0.4265 0.3396 0.0349 0.0523 1.0000 Uiso R H101 H 0.5000 0.4553 0.2649 0.0578 1.0000 Uiso R H111 H 0.4420 0.6355 0.4360 0.0568 1.0000 Uiso R H121 H 0.3115 0.6997 0.3786 0.0504 1.0000 Uiso R H131 H 0.1815 0.1103 0.2593 0.0485 1.0000 Uiso R H132 H 0.2019 0.1929 0.1085 0.0481 1.0000 Uiso R H142 H 0.0693 0.0307 0.1209 0.0486 1.0000 Uiso R H141 H 0.0798 0.1825 -0.0136 0.0496 1.0000 Uiso R H31 H 0.0731 0.6034 0.2628 0.0376 1.0000 Uiso R H61 H 0.1291 0.6095 -0.0255 0.0752 1.0000 Uiso R 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 O1 0.0248(5) 0.0539(6) 0.0389(5) 0.0119(4) 0.0040(4) -0.0038(4) C2 0.0286(6) 0.0384(7) 0.0227(6) 0.0071(5) 0.0056(4) -0.0033(5) N3 0.0255(5) 0.0322(6) 0.0291(5) -0.0008(4) 0.0084(4) 0.0015(4) C4 0.0234(6) 0.0313(6) 0.0250(6) 0.0008(5) 0.0047(4) 0.0012(5) C5 0.0288(6) 0.0308(7) 0.0370(7) 0.0057(5) 0.0095(5) 0.0029(5) O6 0.0290(5) 0.0844(8) 0.0358(5) 0.0241(5) 0.0082(4) 0.0092(5) C7 0.0276(6) 0.0280(6) 0.0385(7) 0.0053(5) 0.0090(5) -0.0015(5) C8 0.0301(7) 0.0415(8) 0.0373(7) 0.0030(6) 0.0069(5) 0.0009(5) C9 0.0317(7) 0.0472(9) 0.0538(9) -0.0013(7) 0.0134(6) 0.0061(6) C10 0.0257(7) 0.0515(9) 0.0648(10) 0.0019(8) 0.0040(6) 0.0010(6) C11 0.0350(7) 0.0554(10) 0.0527(9) -0.0072(7) -0.0002(6) -0.0087(7) C12 0.0353(7) 0.0423(8) 0.0476(8) -0.0084(6) 0.0108(6) -0.0055(6) C13 0.0332(7) 0.0290(7) 0.0519(8) -0.0022(6) 0.0106(6) -0.0003(5) C14 0.0379(7) 0.0401(8) 0.0399(7) -0.0087(6) 0.0100(5) -0.0080(6) 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' 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 O1 C2 N3 124.82(12) yes O1 C2 C14 126.54(12) yes N3 C2 C14 108.63(10) yes C2 N3 C4 115.39(10) yes C2 N3 H31 122.4 no C4 N3 H31 122.2 no N3 C4 C5 111.71(10) yes N3 C4 C13 102.78(9) yes C5 C4 C13 114.78(10) yes N3 C4 H41 109.9 no C5 C4 H41 107.3 no C13 C4 H41 110.4 no C4 C5 O6 111.43(10) yes C4 C5 C7 110.06(10) yes O6 C5 C7 109.51(10) yes C4 C5 H51 107.2 no O6 C5 H51 109.5 no C7 C5 H51 109.1 no C5 O6 H61 110.2 no C5 C7 C8 122.44(11) yes C5 C7 C12 118.86(12) yes C8 C7 C12 118.65(12) yes C7 C8 C9 120.29(13) yes C7 C8 H81 119.3 no C9 C8 H81 120.4 no C8 C9 C10 120.40(13) yes C8 C9 H91 118.2 no C10 C9 H91 121.4 no C9 C10 C11 119.61(13) yes C9 C10 H101 120.7 no C11 C10 H101 119.7 no C10 C11 C12 120.13(14) yes C10 C11 H111 119.3 no C12 C11 H111 120.5 no C7 C12 C11 120.92(13) yes C7 C12 H121 118.6 no C11 C12 H121 120.5 no C4 C13 C14 105.86(10) yes C4 C13 H131 109.5 no C14 C13 H131 109.2 no C4 C13 H132 111.2 no C14 C13 H132 112.4 no H131 C13 H132 108.6 no C13 C14 C2 104.85(10) yes C13 C14 H142 112.3 no C2 C14 H142 111.6 no C13 C14 H141 111.6 no C2 C14 H141 107.5 no H142 C14 H141 108.8 no loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag O1 C2 1.2440(14) yes C2 N3 1.3290(16) yes C2 C14 1.5039(19) yes N3 C4 1.4589(14) yes N3 H31 0.880 no C4 C5 1.5317(16) yes C4 C13 1.5382(18) yes C4 H41 0.989 no C5 O6 1.4148(16) yes C5 C7 1.5111(17) yes C5 H51 1.008 no O6 H61 0.882 no C7 C8 1.3894(19) yes C7 C12 1.3878(19) yes C8 C9 1.3918(18) yes C8 H81 0.955 no C9 C10 1.377(2) yes C9 H91 0.965 no C10 C11 1.383(2) yes C10 H101 0.963 no C11 C12 1.3820(19) yes C11 H111 0.963 no C12 H121 0.939 no C13 C14 1.5173(18) yes C13 H131 0.994 no C13 H132 0.949 no C14 H142 0.955 no C14 H141 1.003 no loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_angle_DHA _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_publ_flag C13 H131 O6 4_555 161 0.99 2.48 3.4416(19) yes N3 H31 O1 3_555 174 0.88 2.05 2.9268(19) yes O6 H61 O1 2_565 159 0.88 1.92 2.7590(19) yes