#------------------------------------------------------------------------------ #$Date: 2013-12-28 09:07:06 +0200 (Sat, 28 Dec 2013) $ #$Revision: 91932 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/50/39/1503917.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_1503917 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 'C9 H15 N1 O2' _chemical_formula_sum 'C9 H15 N O2' _chemical_formula_weight 169.22 _chemical_melting_point ? _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 08-07-01 _audit_creation_method CRYSTALS_ver_12.86 _cell_angle_alpha 90 _cell_angle_beta 120.0222(9) _cell_angle_gamma 90 _cell_formula_units_Z 8 _cell_length_a 18.3496(3) _cell_length_b 9.3578(2) _cell_length_c 11.8645(2) _cell_measurement_reflns_used 2083 _cell_measurement_temperature 150 _cell_measurement_theta_max 27 _cell_measurement_theta_min 5 _cell_volume 1763.94(6) _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 0.992 _diffrn_measured_fraction_theta_max 0.992 _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 0.029 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_h_min -23 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_number 10482 _diffrn_reflns_theta_full 26.931 _diffrn_reflns_theta_max 27.481 _diffrn_reflns_theta_min 5.133 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.090 _exptl_absorpt_correction_T_max 0.99 _exptl_absorpt_correction_T_min 0.95 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.274 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 736 _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.12 _refine_diff_density_max 0.33 _refine_diff_density_min -0.23 _refine_ls_extinction_method None _refine_ls_goodness_of_fit_ref 0.9426 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 109 _refine_ls_number_reflns 2009 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0472 _refine_ls_R_factor_gt 0.0364 _refine_ls_shift/su_max 0.000255 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details ; Method= Modified Sheldrick w=1/[\s^2^(F^2^) + ( 0.03P)^2^ + 1.59P] ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 ; _refine_ls_weighting_scheme calc _refine_ls_wR_factor_all 0.0854 _refine_ls_wR_factor_gt 0.0813 _refine_ls_wR_factor_ref 0.0854 _reflns_limit_h_max 20 _reflns_limit_h_min -23 _reflns_limit_k_max 12 _reflns_limit_k_min 0 _reflns_limit_l_max 15 _reflns_limit_l_min 0 _reflns_number_gt 1658 _reflns_number_total 2009 _reflns_threshold_expression I>2.0\s(I) _oxford_diffrn_Wilson_B_factor 2.16 _oxford_diffrn_Wilson_scale 3.32 _oxford_refine_ls_r_factor_ref 0.0472 _oxford_refine_ls_scale 0.5437(12) _oxford_reflns_number_all 2009 _oxford_reflns_threshold_expression_ref I>-3.0\s(I) _oxford_structure_analysis_title 0060708 _[local]_cod_data_source_file ol900631y_si_002.cif _[local]_cod_data_source_block Compound_32 _[local]_cod_cif_authors_sg_H-M 'C 1 2/c 1 ' _[local]_cod_chemical_formula_sum_orig 'C9 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 '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 1503917 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 0.43989(5) 0.09153(9) 0.56719(8) 0.0268 1.0000 Uani . C2 C 0.39416(7) 0.20871(12) 0.48314(10) 0.0210 1.0000 Uani . C3 C 0.30328(7) 0.15978(12) 0.38818(11) 0.0234 1.0000 Uani . C4 C 0.25698(7) 0.24861(13) 0.26332(11) 0.0268 1.0000 Uani . C5 C 0.31401(7) 0.27903(12) 0.20524(11) 0.0254 1.0000 Uani . C6 C 0.35452(7) 0.13824(12) 0.20190(11) 0.0238 1.0000 Uani . O7 O 0.32494(5) 0.04929(10) 0.11262(8) 0.0331 1.0000 Uani . N8 N 0.42639(6) 0.12528(10) 0.31590(9) 0.0217 1.0000 Uani . C9 C 0.43956(7) 0.24429(12) 0.40556(10) 0.0212 1.0000 Uani . C10 C 0.39080(8) 0.36213(12) 0.30564(11) 0.0264 1.0000 Uani . C11 C 0.53317(7) 0.27251(14) 0.49215(12) 0.0302 1.0000 Uani . C12 C 0.39499(8) 0.33375(14) 0.56709(12) 0.0309 1.0000 Uani . H31 H 0.2716 0.1605 0.4342 0.0289 1.0000 Uiso R H32 H 0.3072 0.0590 0.3647 0.0280 1.0000 Uiso R H41 H 0.2388 0.3399 0.2823 0.0305 1.0000 Uiso R H42 H 0.2059 0.1953 0.2001 0.0309 1.0000 Uiso R H51 H 0.2827 0.3223 0.1186 0.0285 1.0000 Uiso R H101 H 0.4256 0.3977 0.2692 0.0320 1.0000 Uiso R H102 H 0.3757 0.4434 0.3437 0.0315 1.0000 Uiso R H113 H 0.5581 0.2900 0.4376 0.0449 1.0000 Uiso R H112 H 0.5423 0.3565 0.5462 0.0453 1.0000 Uiso R H111 H 0.5619 0.1902 0.5480 0.0439 1.0000 Uiso R H123 H 0.3563 0.4099 0.5144 0.0456 1.0000 Uiso R H122 H 0.4515 0.3755 0.6177 0.0462 1.0000 Uiso R H121 H 0.3775 0.2985 0.6277 0.0450 1.0000 Uiso R H81 H 0.4572 0.0495 0.3396 0.0281 1.0000 Uiso R H11 H 0.4069 0.0502 0.5875 0.0423 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 0.0218(4) 0.0306(5) 0.0272(4) 0.0110(3) 0.0115(4) 0.0065(3) C2 0.0191(5) 0.0214(5) 0.0198(5) 0.0027(4) 0.0078(4) 0.0035(4) C3 0.0178(5) 0.0249(6) 0.0261(6) 0.0015(5) 0.0100(5) 0.0012(4) C4 0.0192(5) 0.0285(6) 0.0259(6) 0.0010(5) 0.0061(5) 0.0066(5) C5 0.0270(6) 0.0234(6) 0.0202(5) 0.0033(4) 0.0077(5) 0.0065(5) C6 0.0233(6) 0.0253(6) 0.0214(5) -0.0003(5) 0.0103(5) 0.0018(4) O7 0.0319(5) 0.0356(5) 0.0257(4) -0.0095(4) 0.0099(4) 0.0023(4) N8 0.0201(5) 0.0213(5) 0.0221(5) -0.0006(4) 0.0093(4) 0.0035(4) C9 0.0204(5) 0.0196(5) 0.0218(5) -0.0019(4) 0.0091(5) -0.0018(4) C10 0.0321(6) 0.0196(6) 0.0263(6) 0.0015(5) 0.0137(5) -0.0003(5) C11 0.0214(6) 0.0344(7) 0.0313(6) -0.0044(5) 0.0106(5) -0.0074(5) C12 0.0313(6) 0.0342(7) 0.0260(6) -0.0059(5) 0.0134(5) 0.0013(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 C2 O1 H11 107.1 no O1 C2 C3 108.84(9) yes O1 C2 C9 105.93(8) yes C3 C2 C9 109.55(9) yes O1 C2 C12 108.63(9) yes C3 C2 C12 110.92(9) yes C9 C2 C12 112.78(9) yes C2 C3 C4 114.77(9) yes C2 C3 H31 108.5 no C4 C3 H31 109.9 no C2 C3 H32 106.4 no C4 C3 H32 109.0 no H31 C3 H32 108.0 no C3 C4 C5 111.14(9) yes C3 C4 H41 109.7 no C5 C4 H41 109.1 no C3 C4 H42 108.4 no C5 C4 H42 110.5 no H41 C4 H42 108.0 no C4 C5 C6 107.55(9) yes C4 C5 C10 108.28(9) yes C6 C5 C10 100.90(9) yes C4 C5 H51 111.9 no C6 C5 H51 111.6 no C10 C5 H51 115.8 no C5 C6 O7 126.36(10) yes C5 C6 N8 107.36(9) yes O7 C6 N8 126.21(11) yes C6 N8 C9 112.52(9) yes C6 N8 H81 123.9 no C9 N8 H81 122.8 no C2 C9 N8 108.81(9) yes C2 C9 C10 109.43(9) yes N8 C9 C10 99.41(8) yes C2 C9 C11 113.32(9) yes N8 C9 C11 109.93(9) yes C10 C9 C11 114.95(10) yes C9 C10 C5 100.97(9) yes C9 C10 H101 108.9 no C5 C10 H101 112.0 no C9 C10 H102 112.7 no C5 C10 H102 112.8 no H101 C10 H102 109.2 no C9 C11 H113 109.1 no C9 C11 H112 110.4 no H113 C11 H112 108.5 no C9 C11 H111 111.4 no H113 C11 H111 107.9 no H112 C11 H111 109.4 no C2 C12 H123 111.9 no C2 C12 H122 111.4 no H123 C12 H122 107.9 no C2 C12 H121 108.7 no H123 C12 H121 108.4 no H122 C12 H121 108.5 no loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag O1 C2 1.4365(13) yes O1 H11 0.848 no C2 C3 1.5427(15) yes C2 C9 1.5555(15) yes C2 C12 1.5318(16) yes C3 C4 1.5323(16) yes C3 H31 0.977 no C3 H32 0.996 no C4 C5 1.5403(17) yes C4 H41 0.984 no C4 H42 0.993 no C5 C6 1.5230(16) yes C5 C10 1.5263(16) yes C5 H51 0.980 no C6 O7 1.2386(14) yes C6 N8 1.3411(14) yes N8 C9 1.4741(14) yes N8 H81 0.862 no C9 C10 1.5364(16) yes C9 C11 1.5198(15) yes C10 H101 0.991 no C10 H102 0.992 no C11 H113 0.975 no C11 H112 0.974 no C11 H111 0.980 no C12 H123 0.979 no C12 H122 0.982 no C12 H121 0.979 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 N8 H81 O1 2_656 163 0.86 2.11 2.9420(18) yes O1 H11 O7 6_555 173 0.85 1.92 2.7592(18) yes _journal_paper_doi 10.1021/ol900631y