#------------------------------------------------------------------------------ #$Date: 2015-01-23 14:30:19 +0200 (Fri, 23 Jan 2015) $ #$Revision: 130086 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/50/39/1503913.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_1503913 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_formula_moiety 'C6 H11 N1 O2' _chemical_formula_sum 'C6 H11 N O2' _chemical_formula_weight 129.16 _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 08-08-07 _audit_creation_method CRYSTALS_ver_12.86 _cell_angle_alpha 90 _cell_angle_beta 90.8101(12) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 8.6393(2) _cell_length_b 5.20040(10) _cell_length_c 14.3361(4) _cell_measurement_reflns_used 1561 _cell_measurement_temperature 150 _cell_measurement_theta_max 27 _cell_measurement_theta_min 5 _cell_volume 644.03(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 0.990 _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 0.000 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_number 7135 _diffrn_reflns_theta_full 25.781 _diffrn_reflns_theta_max 27.426 _diffrn_reflns_theta_min 5.371 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.100 _exptl_absorpt_correction_T_max 0.98 _exptl_absorpt_correction_T_min 0.90 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.332 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 280 _exptl_crystal_size_max 0.44 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.18 _refine_diff_density_max 0.31 _refine_diff_density_min -0.29 _refine_ls_extinction_method None _refine_ls_goodness_of_fit_ref 0.9792 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 82 _refine_ls_number_reflns 1454 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0485 _refine_ls_R_factor_gt 0.0377 _refine_ls_shift/su_max 0.000445 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details ; Method= Modified Sheldrick w=1/[\s^2^(F^2^) + ( 0.03P)^2^ + 0.26P] ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 ; _refine_ls_weighting_scheme calc _refine_ls_wR_factor_all 0.0869 _refine_ls_wR_factor_gt 0.0838 _refine_ls_wR_factor_ref 0.0869 _reflns_limit_h_max 11 _reflns_limit_h_min -11 _reflns_limit_k_max 6 _reflns_limit_k_min 0 _reflns_limit_l_max 18 _reflns_limit_l_min 0 _reflns_number_gt 1184 _reflns_number_total 1454 _reflns_threshold_expression I>2.0\s(I) _oxford_diffrn_Wilson_B_factor 1.96 _oxford_diffrn_Wilson_scale 0.90 _oxford_refine_ls_r_factor_ref 0.0485 _oxford_refine_ls_scale 1.018(5) _oxford_reflns_number_all 1454 _oxford_reflns_threshold_expression_ref I>-3.0\s(I) _oxford_structure_analysis_title 0120808 _[local]_cod_data_source_file ol900631y_si_002.cif _[local]_cod_data_source_block Compound_17 _[local]_cod_cif_authors_sg_H-M 'P 1 21/c 1 ' _[local]_cod_cif_authors_sg_Hall '-P 2ybc ' _[local]_cod_chemical_formula_sum_orig 'C6 H11 N1 O2' _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 2.4.2 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 1503913 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 0.69442(10) 1.12126(17) 0.41937(6) 0.0261 1.0000 Uani . C2 C 0.73340(13) 0.9976(2) 0.48970(8) 0.0189 1.0000 Uani . N3 N 0.69518(11) 1.05329(18) 0.57752(6) 0.0193 1.0000 Uani . C4 C 0.75167(13) 0.8722(2) 0.64879(8) 0.0181 1.0000 Uani . C5 C 0.61957(13) 0.7038(2) 0.68398(8) 0.0214 1.0000 Uani . O6 O 0.54925(9) 0.55345(16) 0.61212(6) 0.0240 1.0000 Uani . C7 C 0.82295(15) 1.0137(2) 0.73165(8) 0.0251 1.0000 Uani . C8 C 0.87147(13) 0.7131(2) 0.59359(8) 0.0205 1.0000 Uani . C9 C 0.83279(14) 0.7585(2) 0.49036(8) 0.0222 1.0000 Uani . H51 H 0.6625 0.5828 0.7319 0.0257 1.0000 Uiso R H52 H 0.5408 0.8154 0.7145 0.0255 1.0000 Uiso R H72 H 0.8615 0.8893 0.7783 0.0370 1.0000 Uiso R H71 H 0.9094 1.1205 0.7115 0.0366 1.0000 Uiso R H73 H 0.7458 1.1245 0.7614 0.0370 1.0000 Uiso R H82 H 0.9748 0.7770 0.6088 0.0221 1.0000 Uiso R H81 H 0.8646 0.5298 0.6098 0.0236 1.0000 Uiso R H92 H 0.9258 0.7869 0.4525 0.0266 1.0000 Uiso R H91 H 0.7723 0.6187 0.4640 0.0272 1.0000 Uiso R H31 H 0.6381 1.1818 0.5907 0.0239 1.0000 Uiso R H61 H 0.4735 0.6361 0.5889 0.0386 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 0.0288(5) 0.0282(5) 0.0214(4) 0.0053(4) -0.0013(3) 0.0041(4) C2 0.0178(5) 0.0185(6) 0.0204(6) 0.0007(5) -0.0004(4) -0.0026(4) N3 0.0226(5) 0.0147(5) 0.0205(5) 0.0007(4) 0.0004(4) 0.0040(4) C4 0.0204(6) 0.0151(5) 0.0187(5) 0.0009(4) -0.0007(4) 0.0022(4) C5 0.0218(6) 0.0203(6) 0.0221(6) 0.0003(5) 0.0026(4) 0.0009(5) O6 0.0212(4) 0.0176(4) 0.0331(5) -0.0028(3) -0.0022(3) 0.0003(3) C7 0.0286(6) 0.0237(6) 0.0229(6) -0.0013(5) -0.0033(5) -0.0003(5) C8 0.0194(6) 0.0177(6) 0.0245(6) 0.0026(5) 0.0014(4) 0.0023(5) C9 0.0234(6) 0.0206(6) 0.0225(6) -0.0013(5) 0.0026(5) 0.0015(5) 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 125.86(11) yes O1 C2 C9 125.47(10) yes N3 C2 C9 108.67(9) yes C2 N3 C4 115.59(9) yes C2 N3 H31 121.9 no C4 N3 H31 122.4 no N3 C4 C5 110.77(9) yes N3 C4 C7 111.11(9) yes C5 C4 C7 108.37(9) yes N3 C4 C8 101.81(8) yes C5 C4 C8 111.69(9) yes C7 C4 C8 113.02(9) yes C4 C5 O6 112.87(9) yes C4 C5 H51 108.4 no O6 C5 H51 107.6 no C4 C5 H52 109.1 no O6 C5 H52 110.4 no H51 C5 H52 108.2 no C5 O6 H61 109.0 no C4 C7 H72 110.0 no C4 C7 H71 110.3 no H72 C7 H71 108.7 no C4 C7 H73 110.7 no H72 C7 H73 108.4 no H71 C7 H73 108.7 no C4 C8 C9 105.85(9) yes C4 C8 H82 108.6 no C9 C8 H82 110.6 no C4 C8 H81 110.7 no C9 C8 H81 111.4 no H82 C8 H81 109.6 no C8 C9 C2 104.42(9) yes C8 C9 H92 112.7 no C2 C9 H92 109.9 no C8 C9 H91 111.7 no C2 C9 H91 108.2 no H92 C9 H91 109.7 no loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag O1 C2 1.2386(13) yes C2 N3 1.3377(14) yes C2 C9 1.5111(16) yes N3 C4 1.4681(14) yes N3 H31 0.853 no C4 C5 1.5298(16) yes C4 C7 1.5203(15) yes C4 C8 1.5506(15) yes C5 O6 1.4226(14) yes C5 H51 0.999 no C5 H52 1.000 no O6 H61 0.847 no C7 H72 0.985 no C7 H71 0.978 no C7 H73 0.983 no C8 C9 1.5308(15) yes C8 H82 0.974 no C8 H81 0.983 no C9 H92 0.987 no C9 H91 0.969 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 N3 H31 O6 1_565 165 0.85 2.10 2.9358(16) yes O6 H61 O1 2_676 159 0.85 1.92 2.7332(16) yes