#------------------------------------------------------------------------------ #$Date: 2013-12-28 09:07:06 +0200 (Sat, 28 Dec 2013) $ #$Revision: 91932 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/50/39/1503916.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_1503916 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 'C8 H13 N O2, H2 O' _chemical_formula_sum 'C8 H15 N O3' _chemical_formula_weight 173.21 _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 08-06-26 _audit_creation_method CRYSTALS_ver_12.86 _cell_angle_alpha 90 _cell_angle_beta 95.2915(8) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 4.97490(10) _cell_length_b 7.86990(10) _cell_length_c 22.0125(5) _cell_measurement_reflns_used 1957 _cell_measurement_temperature 150 _cell_measurement_theta_max 27 _cell_measurement_theta_min 5 _cell_volume 858.16(3) _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 0.989 _diffrn_measured_fraction_theta_max 0.988 _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 0.025 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_number 10581 _diffrn_reflns_theta_full 26.943 _diffrn_reflns_theta_max 27.492 _diffrn_reflns_theta_min 5.181 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.102 _exptl_absorpt_correction_T_max 0.97 _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 1.341 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_method 'not measured' _exptl_crystal_description needle _exptl_crystal_F_000 376 _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.28 _refine_diff_density_max 0.30 _refine_diff_density_min -0.20 _refine_ls_extinction_coef 350(50) _refine_ls_extinction_method 'Larson (1970), Equation 22' _refine_ls_goodness_of_fit_ref 1.0088 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 110 _refine_ls_number_reflns 1954 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0434 _refine_ls_R_factor_gt 0.0389 _refine_ls_shift/su_max 0.000714 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details ; Method= Modified Sheldrick w=1/[\s^2^(F^2^) + ( 0.04P)^2^ + 0.44P] ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 ; _refine_ls_weighting_scheme calc _refine_ls_wR_factor_all 0.0966 _refine_ls_wR_factor_gt 0.0949 _refine_ls_wR_factor_ref 0.0966 _reflns_limit_h_max 6 _reflns_limit_h_min -6 _reflns_limit_k_max 10 _reflns_limit_k_min 0 _reflns_limit_l_max 28 _reflns_limit_l_min 0 _reflns_number_gt 1754 _reflns_number_total 1954 _reflns_threshold_expression I>2.0\s(I) _oxford_diffrn_Wilson_B_factor 1.98 _oxford_diffrn_Wilson_scale 0.29 _oxford_refine_ls_r_factor_ref 0.0434 _oxford_refine_ls_scale 1.703(19) _oxford_reflns_number_all 1954 _oxford_reflns_threshold_expression_ref I>-3.0\s(I) _oxford_structure_analysis_title 0040608 _[local]_cod_data_source_file ol900631y_si_002.cif _[local]_cod_data_source_block Compound_30 _[local]_cod_cif_authors_sg_H-M 'P 1 21/c 1 ' _[local]_cod_chemical_formula_sum_orig 'C8 H15 N1 O3' _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 ; _cod_database_code 1503916 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 0.04947(17) 0.72572(11) 0.50227(4) 0.0248 1.0000 Uani . C2 C 0.2100(2) 0.69503(15) 0.46360(5) 0.0198 1.0000 Uani . N3 N 0.23439(19) 0.54502(12) 0.43578(4) 0.0204 1.0000 Uani . C4 C 0.4637(2) 0.54066(14) 0.39831(5) 0.0191 1.0000 Uani . C5 C 0.4213(2) 0.42239(14) 0.34335(5) 0.0199 1.0000 Uani . O6 O 0.34467(17) 0.25635(10) 0.36212(4) 0.0254 1.0000 Uani . H7 H 0.4857 0.2007 0.3702 0.0401 1.0000 Uiso R C8 C 0.2177(2) 0.48881(16) 0.29376(6) 0.0236 1.0000 Uani . C9 C 0.3033(3) 0.66514(16) 0.27398(6) 0.0258 1.0000 Uani . C10 C 0.3088(2) 0.78858(15) 0.32747(5) 0.0232 1.0000 Uani . C11 C 0.4959(2) 0.73147(14) 0.38288(5) 0.0206 1.0000 Uani . C12 C 0.4142(2) 0.81713(15) 0.44129(5) 0.0222 1.0000 Uani . H13 H 0.5737 0.8297 0.4718 0.0277 1.0000 Uiso R H14 H 0.3321 0.9356 0.4343 0.0272 1.0000 Uiso R H15 H 0.6959 0.7563 0.3780 0.0264 1.0000 Uiso R H16 H 0.3564 0.9057 0.3146 0.0284 1.0000 Uiso R H17 H 0.1226 0.7999 0.3400 0.0274 1.0000 Uiso R H18 H 0.4800 0.6533 0.2582 0.0319 1.0000 Uiso R H19 H 0.1800 0.7053 0.2411 0.0318 1.0000 Uiso R H20 H 0.0395 0.4983 0.3101 0.0287 1.0000 Uiso R H21 H 0.2051 0.4147 0.2591 0.0285 1.0000 Uiso R H22 H 0.5981 0.4160 0.3257 0.0238 1.0000 Uiso R H23 H 0.6251 0.5004 0.4239 0.0239 1.0000 Uiso R H24 H 0.1533 0.4585 0.4443 0.0255 1.0000 Uiso R O25 O 0.15842(17) 0.60528(11) 0.11163(4) 0.0271 1.0000 Uani . H26 H 0.1286 0.6160 0.0736 0.0449 1.0000 Uiso R H27 H 0.0147 0.6332 0.1268 0.0452 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 0.0277(5) 0.0266(5) 0.0211(4) -0.0010(3) 0.0078(3) 0.0003(3) C2 0.0200(5) 0.0222(6) 0.0169(5) 0.0019(4) 0.0001(4) 0.0008(4) N3 0.0222(5) 0.0179(5) 0.0218(5) 0.0018(4) 0.0062(4) -0.0021(4) C4 0.0158(5) 0.0194(5) 0.0222(6) 0.0018(4) 0.0027(4) 0.0004(4) C5 0.0181(5) 0.0173(5) 0.0254(6) -0.0001(4) 0.0071(4) -0.0015(4) O6 0.0247(4) 0.0167(4) 0.0357(5) 0.0024(3) 0.0082(4) -0.0010(3) C8 0.0239(6) 0.0240(6) 0.0230(6) -0.0022(4) 0.0030(5) -0.0025(5) C9 0.0322(6) 0.0250(6) 0.0207(6) 0.0028(5) 0.0053(5) 0.0019(5) C10 0.0279(6) 0.0196(6) 0.0229(6) 0.0036(4) 0.0073(5) 0.0014(5) C11 0.0190(5) 0.0188(5) 0.0247(6) -0.0003(4) 0.0060(4) -0.0026(4) C12 0.0231(6) 0.0206(6) 0.0232(6) -0.0022(4) 0.0033(4) -0.0030(4) O25 0.0263(5) 0.0288(5) 0.0265(5) 0.0013(4) 0.0035(3) 0.0015(4) 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 125.08(11) yes O1 C2 C12 126.29(11) yes N3 C2 C12 108.62(9) yes C2 N3 C4 112.64(9) yes C2 N3 H24 123.9 no C4 N3 H24 122.1 no N3 C4 C5 113.71(9) yes N3 C4 C11 101.64(9) yes C5 C4 C11 115.25(9) yes N3 C4 H23 108.6 no C5 C4 H23 107.6 no C11 C4 H23 109.8 no C4 C5 O6 110.41(9) yes C4 C5 C8 113.32(9) yes O6 C5 C8 110.18(9) yes C4 C5 H22 106.2 no O6 C5 H22 109.6 no C8 C5 H22 107.0 no C5 O6 H7 107.5 no C5 C8 C9 109.51(10) yes C5 C8 H20 109.1 no C9 C8 H20 108.5 no C5 C8 H21 110.8 no C9 C8 H21 109.0 no H20 C8 H21 109.9 no C8 C9 C10 110.15(10) yes C8 C9 H18 107.3 no C10 C9 H18 112.5 no C8 C9 H19 109.8 no C10 C9 H19 109.7 no H18 C9 H19 107.3 no C9 C10 C11 113.22(10) yes C9 C10 H16 110.9 no C11 C10 H16 110.7 no C9 C10 H17 108.7 no C11 C10 H17 108.6 no H16 C10 H17 104.3 no C10 C11 C4 113.00(9) yes C10 C11 C12 110.40(9) yes C4 C11 C12 101.57(9) yes C10 C11 H15 112.6 no C4 C11 H15 109.1 no C12 C11 H15 109.7 no C11 C12 C2 103.30(9) yes C11 C12 H13 110.6 no C2 C12 H13 111.2 no C11 C12 H14 114.0 no C2 C12 H14 110.9 no H13 C12 H14 107.0 no H26 O25 H27 106.8 no loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag O1 C2 1.2434(14) yes C2 N3 1.3406(15) yes C2 C12 1.5128(16) yes N3 C4 1.4683(14) yes N3 H24 0.822 no C4 C5 1.5256(16) yes C4 C11 1.5512(15) yes C4 H23 0.990 no C5 O6 1.4327(13) yes C5 C8 1.5123(16) yes C5 H22 0.996 no O6 H7 0.832 no C8 C9 1.5268(17) yes C8 H20 0.989 no C8 H21 0.959 no C9 C10 1.5246(17) yes C9 H18 0.979 no C9 H19 0.958 no C10 C11 1.5321(17) yes C10 H16 0.999 no C10 H17 0.994 no C11 C12 1.5392(16) yes C11 H15 1.029 no C12 H13 0.997 no C12 H14 1.024 no O25 H26 0.840 no O25 H27 0.845 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 O6 H7 O25 3_645 171 0.83 1.93 2.7559(17) yes C12 H13 O1 1_655 144 1.00 2.54 3.3949(17) yes N3 H24 O1 2_566 160 0.82 2.17 2.9579(17) yes O25 H26 O1 4_564 147 0.84 2.01 2.7600(17) yes O25 H27 O6 3_555 160 0.85 2.07 2.8772(17) yes _journal_paper_doi 10.1021/ol900631y