#------------------------------------------------------------------------------ #$Date: 2016-02-14 16:26:36 +0200 (Sun, 14 Feb 2016) $ #$Revision: 176435 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/50/39/1503915.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_1503915 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 'C17 H17 N1 O2' _chemical_formula_sum 'C17 H17 N O2' _chemical_formula_weight 267.33 _space_group_IT_number 15 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-C 2yc' _symmetry_space_group_name_H-M 'C 1 2/c 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _audit_creation_date 08-08-27 _audit_creation_method CRYSTALS_ver_12.86 _cell_angle_alpha 90 _cell_angle_beta 109.973(2) _cell_angle_gamma 90 _cell_formula_units_Z 8 _cell_length_a 32.8860(12) _cell_length_b 6.0205(3) _cell_length_c 14.9007(7) _cell_measurement_reflns_used 8960 _cell_measurement_temperature 150 _cell_measurement_theta_max 25 _cell_measurement_theta_min 5 _cell_volume 2772.7(2) _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 0.975 _diffrn_measured_fraction_theta_max 0.958 _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 0.086 _diffrn_reflns_limit_h_max 42 _diffrn_reflns_limit_h_min -42 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_number 5251 _diffrn_reflns_theta_full 25.400 _diffrn_reflns_theta_max 27.410 _diffrn_reflns_theta_min 5.268 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.084 _exptl_absorpt_correction_T_max 0.99 _exptl_absorpt_correction_T_min 0.97 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.281 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 1136 _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.12 _refine_diff_density_max 0.40 _refine_diff_density_min -0.41 _refine_ls_extinction_coef 0.000 _refine_ls_extinction_method 'Larson (1970), Equation 22' _refine_ls_goodness_of_fit_ref 0.9061 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 181 _refine_ls_number_reflns 3521 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0989 _refine_ls_R_factor_gt 0.0523 _refine_ls_shift/su_max 0.000217 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details ; Method= Modified Sheldrick w=1/[\s^2^(F^2^) + ( 0.03P)^2^ + 4.18P] ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 ; _refine_ls_weighting_scheme calc _refine_ls_wR_factor_all 0.1168 _refine_ls_wR_factor_gt 0.0988 _refine_ls_wR_factor_ref 0.1163 _reflns_limit_h_max 39 _reflns_limit_h_min -42 _reflns_limit_k_max 7 _reflns_limit_k_min -7 _reflns_limit_l_max 19 _reflns_limit_l_min 0 _reflns_number_gt 2205 _reflns_number_total 3027 _reflns_threshold_expression I>2.0\s(I) _oxford_diffrn_Wilson_B_factor 2.35 _oxford_diffrn_Wilson_scale 45.39 _oxford_refine_ls_r_factor_ref 0.0985 _oxford_refine_ls_scale 0.16238(10) _oxford_reflns_number_all 3525 _oxford_reflns_threshold_expression_ref I>-2.0\s(I) _oxford_structure_analysis_title 0130808 _cod_data_source_file ol900631y_si_002.cif _cod_data_source_block Compound_28 _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_original_sg_symbol_H-M 'C 1 2/c 1 ' _cod_original_formula_sum 'C17 H17 N1 O2' _cod_database_code 1503915 loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z x+1/2,y+1/2,z -x+1/2,-y+1/2,-z -x,y,-z+1/2 x,-y,z+1/2 -x+1/2,y+1/2,-z+1/2 x+1/2,-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 0.24158(5) 1.0178(2) 0.41576(10) 0.0373 1.0000 Uani . C2 C 0.21616(8) 0.9635(4) 0.45742(14) 0.0331 1.0000 Uani . N3 N 0.21529(6) 1.0487(3) 0.53938(11) 0.0340 1.0000 Uani . C4 C 0.17904(7) 0.9725(3) 0.56627(14) 0.0309 1.0000 Uani . C5 C 0.16256(7) 0.7635(3) 0.50411(13) 0.0314 1.0000 Uani . C6 C 0.18128(7) 0.7928(4) 0.42247(14) 0.0361 1.0000 Uani . C7 C 0.11437(7) 0.7289(4) 0.47006(14) 0.0321 1.0000 Uani . C8 C 0.08581(8) 0.8903(4) 0.41730(15) 0.0382 1.0000 Uani . C9 C 0.04173(8) 0.8562(4) 0.38458(16) 0.0472 1.0000 Uani . C10 C 0.02456(9) 0.6597(4) 0.40370(17) 0.0501 1.0000 Uani . C11 C 0.05222(9) 0.4976(4) 0.45583(18) 0.0485 1.0000 Uani . C12 C 0.09643(8) 0.5324(4) 0.48834(16) 0.0405 1.0000 Uani . C13 C 0.19119(7) 0.9258(3) 0.67322(14) 0.0326 1.0000 Uani . O14 O 0.20959(5) 1.1268(2) 0.72176(10) 0.0402 1.0000 Uani . C15 C 0.15145(7) 0.8550(4) 0.69493(13) 0.0306 1.0000 Uani . C16 C 0.14842(8) 0.6457(4) 0.73179(14) 0.0384 1.0000 Uani . C17 C 0.11093(9) 0.5811(4) 0.74781(16) 0.0427 1.0000 Uani . C18 C 0.07629(8) 0.7207(4) 0.72661(15) 0.0433 1.0000 Uani . C19 C 0.07861(8) 0.9304(4) 0.69002(16) 0.0411 1.0000 Uani . C20 C 0.11607(8) 0.9958(4) 0.67505(14) 0.0353 1.0000 Uani . H41 H 0.1571 1.0894 0.5480 0.0352 1.0000 Uiso R H51 H 0.1777 0.6350 0.5412 0.0343 1.0000 Uiso R H61 H 0.1926 0.6589 0.4072 0.0422 1.0000 Uiso R H62 H 0.1586 0.8544 0.3661 0.0429 1.0000 Uiso R H81 H 0.0964 1.0261 0.4048 0.0439 1.0000 Uiso R H91 H 0.0231 0.9706 0.3510 0.0540 1.0000 Uiso R H101 H -0.0060 0.6404 0.3822 0.0581 1.0000 Uiso R H111 H 0.0407 0.3614 0.4673 0.0602 1.0000 Uiso R H121 H 0.1156 0.4219 0.5229 0.0502 1.0000 Uiso R H131 H 0.2137 0.8118 0.6914 0.0361 1.0000 Uiso R H161 H 0.1721 0.5479 0.7451 0.0451 1.0000 Uiso R H171 H 0.1105 0.4352 0.7745 0.0529 1.0000 Uiso R H181 H 0.0504 0.6758 0.7376 0.0521 1.0000 Uiso R H191 H 0.0542 1.0312 0.6745 0.0498 1.0000 Uiso R H201 H 0.1183 1.1422 0.6548 0.0429 1.0000 Uiso R H31 H 0.2322 1.1536 0.5670 0.0379 1.0000 Uiso R H141 H 0.2186 1.0961 0.7775 0.0577 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 0.0351(10) 0.0492(10) 0.0324(8) 0.0006(7) 0.0178(7) -0.0018(8) C2 0.0336(15) 0.0383(14) 0.0273(12) 0.0018(10) 0.0101(11) 0.0032(11) N3 0.0328(12) 0.0435(12) 0.0271(10) -0.0041(8) 0.0121(9) -0.0067(9) C4 0.0314(14) 0.0341(13) 0.0293(11) 0.0005(10) 0.0134(10) 0.0009(11) C5 0.0368(15) 0.0307(13) 0.0275(12) 0.0025(10) 0.0122(11) 0.0032(11) C6 0.0315(15) 0.0440(15) 0.0339(13) -0.0023(10) 0.0126(11) -0.0020(11) C7 0.0368(16) 0.0359(14) 0.0252(11) -0.0027(10) 0.0126(11) -0.0027(11) C8 0.0328(16) 0.0424(15) 0.0372(13) 0.0037(11) 0.0091(11) -0.0027(12) C9 0.0393(18) 0.0525(17) 0.0471(15) 0.0032(12) 0.0115(13) 0.0032(13) C10 0.0340(17) 0.0599(19) 0.0568(16) -0.0107(14) 0.0159(13) -0.0083(14) C11 0.0507(19) 0.0420(16) 0.0605(16) -0.0057(13) 0.0289(14) -0.0113(14) C12 0.0452(18) 0.0364(14) 0.0436(14) 0.0009(11) 0.0198(12) -0.0004(12) C13 0.0309(15) 0.0386(14) 0.0277(11) 0.0005(10) 0.0092(10) 0.0009(11) O14 0.0440(11) 0.0467(10) 0.0298(8) -0.0015(7) 0.0123(7) -0.0086(8) C15 0.0353(15) 0.0358(13) 0.0219(11) -0.0006(10) 0.0112(10) -0.0003(11) C16 0.0463(17) 0.0386(15) 0.0343(13) 0.0060(11) 0.0191(12) 0.0093(12) C17 0.0545(19) 0.0383(15) 0.0424(14) 0.0011(11) 0.0255(13) -0.0032(13) C18 0.0437(18) 0.0522(17) 0.0406(14) -0.0059(12) 0.0230(13) -0.0105(13) C19 0.0343(15) 0.0486(16) 0.0429(13) 0.0049(12) 0.0165(12) 0.0072(12) C20 0.0416(16) 0.0335(14) 0.0343(12) 0.0009(10) 0.0175(11) -0.0002(11) 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 125.8(2) yes O1 C2 C6 125.00(18) yes N3 C2 C6 109.23(19) yes C2 N3 C4 114.00(17) yes C2 N3 H31 121.0 no C4 N3 H31 124.2 no N3 C4 C5 104.11(16) yes N3 C4 C13 113.41(18) yes C5 C4 C13 112.79(16) yes N3 C4 H41 107.0 no C5 C4 H41 110.2 no C13 C4 H41 109.2 no C4 C5 C6 103.04(16) yes C4 C5 C7 115.35(18) yes C6 C5 C7 113.97(17) yes C4 C5 H51 107.3 no C6 C5 H51 105.7 no C7 C5 H51 110.7 no C5 C6 C2 105.54(17) yes C5 C6 H61 112.7 no C2 C6 H61 110.6 no C5 C6 H62 108.9 no C2 C6 H62 107.8 no H61 C6 H62 111.1 no C5 C7 C8 121.5(2) yes C5 C7 C12 121.4(2) yes C8 C7 C12 117.1(2) yes C7 C8 C9 121.4(2) yes C7 C8 H81 119.9 no C9 C8 H81 118.7 no C8 C9 C10 120.6(2) yes C8 C9 H91 119.5 no C10 C9 H91 119.8 no C9 C10 C11 119.0(3) yes C9 C10 H101 119.6 no C11 C10 H101 121.4 no C10 C11 C12 120.2(2) yes C10 C11 H111 119.3 no C12 C11 H111 120.5 no C7 C12 C11 121.8(2) yes C7 C12 H121 117.4 no C11 C12 H121 120.8 no C4 C13 O14 106.57(16) yes C4 C13 C15 109.71(17) yes O14 C13 C15 112.15(16) yes C4 C13 H131 108.8 no O14 C13 H131 107.6 no C15 C13 H131 111.8 no C13 O14 H141 105.7 no C13 C15 C16 121.6(2) yes C13 C15 C20 120.3(2) yes C16 C15 C20 118.0(2) yes C15 C16 C17 120.6(2) yes C15 C16 H161 119.0 no C17 C16 H161 120.4 no C16 C17 C18 120.5(2) yes C16 C17 H171 117.7 no C18 C17 H171 121.8 no C17 C18 C19 119.9(2) yes C17 C18 H181 120.4 no C19 C18 H181 119.7 no C18 C19 C20 119.6(2) yes C18 C19 H191 120.8 no C20 C19 H191 119.6 no C15 C20 C19 121.3(2) yes C15 C20 H201 119.3 no C19 C20 H201 119.3 no loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag O1 C2 1.243(2) yes C2 N3 1.334(2) yes C2 C6 1.495(3) yes N3 C4 1.455(3) yes N3 H31 0.848 no C4 C5 1.547(3) yes C4 C13 1.531(3) yes C4 H41 0.977 no C5 C6 1.550(3) yes C5 C7 1.504(3) yes C5 H51 0.982 no C6 H61 0.947 no C6 H62 0.984 no C7 C8 1.393(3) yes C7 C12 1.390(3) yes C8 C9 1.378(3) yes C8 H81 0.932 no C9 C10 1.382(3) yes C9 H91 0.943 no C10 C11 1.379(3) yes C10 H101 0.952 no C11 C12 1.382(3) yes C11 H111 0.943 no C12 H121 0.940 no C13 O14 1.433(2) yes C13 C15 1.511(3) yes C13 H131 0.978 no O14 H141 0.802 no C15 C16 1.392(3) yes C15 C20 1.387(3) yes C16 C17 1.389(3) yes C16 H161 0.940 no C17 C18 1.363(3) yes C17 H171 0.967 no C18 C19 1.388(3) yes C18 H181 0.958 no C19 C20 1.382(3) yes C19 H191 0.969 no C20 H201 0.942 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 O1 4_576 156 0.85 2.14 2.937(3) yes O14 H141 O1 6_575 174 0.80 2.05 2.854(3) yes