#------------------------------------------------------------------------------ #$Date: 2012-03-07 12:57:48 +0200 (Wed, 07 Mar 2012) $ #$Revision: 39189 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/50/39/1503914.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_1503914 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_volume 11 _journal_year 2009 _chemical_formula_moiety 'C12 H15 N1 O2' _chemical_formula_sum 'C12 H15 N O2' _chemical_formula_weight 205.26 _chemical_melting_point ? _space_group_IT_number 148 _symmetry_cell_setting trigonal _symmetry_space_group_name_Hall '-R 3' _symmetry_space_group_name_H-M 'R -3 :H' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _audit_creation_date 08-08-07 _audit_creation_method CRYSTALS_ver_12.86 _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 120 _cell_formula_units_Z 18 _cell_length_a 22.3219(4) _cell_length_b 22.3219(4) _cell_length_c 12.1112(3) _cell_measurement_reflns_used 13172 _cell_measurement_temperature 150 _cell_measurement_theta_max 27 _cell_measurement_theta_min 5 _cell_volume 5226.13(19) _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 0.987 _diffrn_measured_fraction_theta_max 0.987 _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 0.000 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_h_min -28 _diffrn_reflns_limit_k_max 28 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_number 2635 _diffrn_reflns_theta_full 26.941 _diffrn_reflns_theta_max 27.491 _diffrn_reflns_theta_min 5.371 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.080 _exptl_absorpt_correction_T_max 0.99 _exptl_absorpt_correction_T_min 0.88 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.174 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 1980 _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.50 _exptl_crystal_size_min 0.15 _platon_squeeze_details ; The discrete Fourier transform of the void region were treated as contributions to the A and B parts of the calculated structure factors. ; _refine_diff_density_max 0.30 _refine_diff_density_min -0.25 _refine_ls_extinction_method None _refine_ls_goodness_of_fit_ref 0.9521 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 136 _refine_ls_number_reflns 2635 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0548 _refine_ls_R_factor_gt 0.0411 _refine_ls_shift/su_max 0.000694 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details ; Method= Modified Sheldrick w=1/[\s^2^(F^2^) + ( 0.05P)^2^ + 4.74P] ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 ; _refine_ls_weighting_scheme calc _refine_ls_wR_factor_all 0.1077 _refine_ls_wR_factor_gt 0.1007 _refine_ls_wR_factor_ref 0.1077 _reflns_limit_h_max 14 _reflns_limit_h_min -28 _reflns_limit_k_max 28 _reflns_limit_k_min 0 _reflns_limit_l_max 15 _reflns_limit_l_min 0 _reflns_number_gt 2082 _reflns_number_total 2635 _reflns_threshold_expression I>2.0\s(I) _oxford_diffrn_Wilson_B_factor 2.67 _oxford_diffrn_Wilson_scale 10.49 _oxford_refine_ls_r_factor_ref 0.0548 _oxford_refine_ls_scale 0.3106(4) _oxford_reflns_number_all 2635 _oxford_reflns_threshold_expression_ref I>-3.0\s(I) _oxford_structure_analysis_title 0110808 _[local]_cod_data_source_file ol900631y_si_002.cif _[local]_cod_data_source_block Compound_20 _[local]_cod_cif_authors_sg_H-M 'R -3 ' _[local]_cod_chemical_formula_sum_orig 'C12 H15 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 'Trigonal' changed to 'trigonal' 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 ; _cod_database_code 1503914 loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z x+1/3,y+2/3,z+2/3 -x+1/3,-y+2/3,-z+2/3 x+2/3,y+1/3,z+1/3 -x+2/3,-y+1/3,-z+1/3 -y,x-y,z y,-x+y,-z -y+1/3,x-y+2/3,z+2/3 y+1/3,-x+y+2/3,-z+2/3 -y+2/3,x-y+1/3,z+1/3 y+2/3,-x+y+1/3,-z+1/3 -x+y,-x,z x-y,x,-z -x+y+1/3,-x+2/3,z+2/3 x-y+1/3,x+2/3,-z+2/3 -x+y+2/3,-x+1/3,z+1/3 x-y+2/3,x+1/3,-z+1/3 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 0.41697(5) 0.45368(5) 0.32853(8) 0.0397 1.0000 Uani . C2 C 0.49032(7) 0.49172(6) 0.32980(10) 0.0319 1.0000 Uani . C3 C 0.52208(6) 0.45429(6) 0.27073(9) 0.0289 1.0000 Uani . C4 C 0.48581(6) 0.40604(6) 0.18846(10) 0.0313 1.0000 Uani . C5 C 0.51646(7) 0.37482(7) 0.13044(11) 0.0391 1.0000 Uani . C6 C 0.58369(8) 0.39102(8) 0.15389(13) 0.0455 1.0000 Uani . C7 C 0.61977(8) 0.43782(8) 0.23681(13) 0.0451 1.0000 Uani . C8 C 0.58930(7) 0.46912(7) 0.29554(11) 0.0368 1.0000 Uani . C9 C 0.51190(6) 0.56359(6) 0.27918(10) 0.0318 1.0000 Uani . N10 N 0.58751(5) 0.60698(5) 0.28567(8) 0.0303 1.0000 Uani . C11 C 0.62091(6) 0.61501(6) 0.19111(9) 0.0264 1.0000 Uani . O12 O 0.68482(4) 0.64689(4) 0.17923(7) 0.0309 1.0000 Uani . C13 C 0.56883(6) 0.57923(6) 0.10006(10) 0.0300 1.0000 Uani . C14 C 0.49937(7) 0.56086(7) 0.15328(11) 0.0330 1.0000 Uani . C15 C 0.47789(8) 0.59800(8) 0.34215(14) 0.0501 1.0000 Uani . H21 H 0.5078 0.5004 0.4060 0.0367 1.0000 Uiso R H41 H 0.4404 0.3948 0.1743 0.0362 1.0000 Uiso R H51 H 0.4907 0.3410 0.0749 0.0475 1.0000 Uiso R H61 H 0.6039 0.3688 0.1138 0.0533 1.0000 Uiso R H71 H 0.6666 0.4485 0.2546 0.0530 1.0000 Uiso R H81 H 0.6140 0.5018 0.3533 0.0440 1.0000 Uiso R H131 H 0.5798 0.6107 0.0379 0.0368 1.0000 Uiso R H132 H 0.5699 0.5369 0.0796 0.0366 1.0000 Uiso R H142 H 0.4874 0.5972 0.1349 0.0415 1.0000 Uiso R H141 H 0.4622 0.5157 0.1275 0.0411 1.0000 Uiso R H153 H 0.4987 0.6454 0.3169 0.0716 1.0000 Uiso R H152 H 0.4856 0.5976 0.4215 0.0732 1.0000 Uiso R H151 H 0.4272 0.5737 0.3270 0.0712 1.0000 Uiso R H11 H 0.4045 0.4191 0.3711 0.0578 1.0000 Uiso R H101 H 0.6080 0.6219 0.3509 0.0368 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 0.0315(5) 0.0377(5) 0.0417(5) 0.0114(4) 0.0101(4) 0.0111(4) C2 0.0321(6) 0.0319(6) 0.0232(6) 0.0024(5) 0.0027(5) 0.0097(5) C3 0.0294(6) 0.0252(6) 0.0242(6) 0.0066(4) -0.0004(5) 0.0076(5) C4 0.0290(6) 0.0273(6) 0.0300(6) 0.0030(5) -0.0036(5) 0.0085(5) C5 0.0460(8) 0.0294(6) 0.0372(7) -0.0005(5) -0.0023(6) 0.0153(6) C6 0.0505(8) 0.0409(8) 0.0506(9) 0.0055(6) 0.0058(7) 0.0271(7) C7 0.0351(7) 0.0438(8) 0.0562(9) 0.0102(7) -0.0030(6) 0.0197(6) C8 0.0344(7) 0.0317(6) 0.0350(7) 0.0034(5) -0.0097(5) 0.0096(5) C9 0.0312(6) 0.0285(6) 0.0297(6) -0.0002(5) 0.0054(5) 0.0104(5) N10 0.0326(5) 0.0272(5) 0.0225(5) -0.0032(4) 0.0017(4) 0.0085(4) C11 0.0319(6) 0.0208(5) 0.0243(6) 0.0015(4) 0.0010(5) 0.0116(5) O12 0.0290(4) 0.0317(4) 0.0277(4) 0.0036(3) 0.0002(3) 0.0119(4) C13 0.0316(6) 0.0311(6) 0.0220(5) 0.0031(5) -0.0004(5) 0.0116(5) C14 0.0305(6) 0.0315(6) 0.0333(6) 0.0045(5) -0.0006(5) 0.0129(5) C15 0.0508(9) 0.0405(8) 0.0573(9) -0.0011(7) 0.0192(7) 0.0215(7) 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 C2 O1 H11 107.0 no O1 C2 C3 112.48(10) yes O1 C2 C9 106.46(10) yes C3 C2 C9 113.19(9) yes O1 C2 H21 110.7 no C3 C2 H21 107.6 no C9 C2 H21 106.2 no C2 C3 C4 120.82(11) yes C2 C3 C8 120.64(11) yes C4 C3 C8 118.52(12) yes C3 C4 C5 120.62(12) yes C3 C4 H41 118.4 no C5 C4 H41 121.0 no C4 C5 C6 120.45(13) yes C4 C5 H51 119.9 no C6 C5 H51 119.6 no C5 C6 C7 119.48(14) yes C5 C6 H61 119.5 no C7 C6 H61 121.0 no C6 C7 C8 120.37(13) yes C6 C7 H71 119.7 no C8 C7 H71 119.9 no C3 C8 C7 120.53(12) yes C3 C8 H81 118.4 no C7 C8 H81 121.0 no C2 C9 N10 108.73(10) yes C2 C9 C14 113.10(10) yes N10 C9 C14 101.79(9) yes C2 C9 C15 110.32(11) yes N10 C9 C15 109.74(11) yes C14 C9 C15 112.75(12) yes C9 N10 C11 115.14(10) yes C9 N10 H101 120.0 no C11 N10 H101 124.4 no N10 C11 O12 125.63(11) yes N10 C11 C13 109.06(10) yes O12 C11 C13 125.31(10) yes C11 C13 C14 104.05(10) yes C11 C13 H131 109.5 no C14 C13 H131 112.0 no C11 C13 H132 107.9 no C14 C13 H132 110.8 no H131 C13 H132 112.2 no C9 C14 C13 105.38(10) yes C9 C14 H142 107.8 no C13 C14 H142 109.5 no C9 C14 H141 113.4 no C13 C14 H141 111.3 no H142 C14 H141 109.3 no C9 C15 H153 107.8 no C9 C15 H152 110.6 no H153 C15 H152 109.3 no C9 C15 H151 110.5 no H153 C15 H151 109.2 no H152 C15 H151 109.4 no loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag O1 C2 1.4184(15) yes O1 H11 0.851 no C2 C3 1.5183(18) yes C2 C9 1.5519(17) yes C2 H21 0.983 no C3 C4 1.3915(17) yes C3 C8 1.3979(18) yes C4 C5 1.3871(19) yes C4 H41 0.930 no C5 C6 1.386(2) yes C5 H51 0.959 no C6 C7 1.381(2) yes C6 H61 0.953 no C7 C8 1.390(2) yes C7 H71 0.974 no C8 H81 0.960 no C9 N10 1.4690(16) yes C9 C14 1.5459(18) yes C9 C15 1.5269(18) yes N10 C11 1.3289(15) yes N10 H101 0.890 no C11 O12 1.2438(14) yes C11 C13 1.5090(16) yes C13 C14 1.5336(17) yes C13 H131 0.974 no C13 H132 0.989 no C14 H142 0.997 no C14 H141 0.982 no C15 H153 0.968 no C15 H152 0.978 no C15 H151 0.997 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 C4 H41 O12 12_455 146 0.93 2.59 3.400(2) yes O1 H11 O12 16_545 168 0.85 1.92 2.761(2) yes N10 H101 O12 17_565 165 0.89 2.03 2.899(2) yes loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 0.000 0.000 0.000 18 0 ' ' 2 0.333 0.667 0.167 141 3 ' ' 3 0.667 0.333 0.333 20 0 ' ' 4 0.000 0.000 0.500 142 3 ' ' 5 0.333 0.667 0.667 20 0 ' ' 6 0.667 0.333 0.833 141 3 ' '