#------------------------------------------------------------------------------ #$Date: 2013-12-28 09:07:06 +0200 (Sat, 28 Dec 2013) $ #$Revision: 91932 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/50/21/1502105.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_1502105 loop_ _publ_author_name 'Donohoe, Timothy J.' 'Connolly, Matthew J.' 'Rathi, Akshat H.' 'Walton, Lesley' _publ_section_title ; Intramolecular hydride addition to pyridinium salts: new routes to enantiopure dihydropyridones. ; _journal_issue 8 _journal_name_full 'Organic letters' _journal_page_first 2074 _journal_page_last 2077 _journal_volume 13 _journal_year 2011 _chemical_compound_source Synthetic _chemical_formula_moiety 'C17 H18 N2 O5' _chemical_formula_sum 'C17 H18 N2 O5' _chemical_formula_weight 330.34 _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 _cell_angle_alpha 90 _cell_angle_beta 112.2564(12) _cell_angle_gamma 90 _cell_formula_units_Z 8 _cell_length_a 35.6530(8) _cell_length_b 6.9183(2) _cell_length_c 14.1033(4) _cell_measurement_reflns_used 3720 _cell_measurement_temperature 150 _cell_measurement_theta_max 27 _cell_measurement_theta_min 5 _cell_volume 3219.52(15) _computing_cell_refinement 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_data_collection 'COLLECT (Nonius, 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 0.991 _diffrn_measured_fraction_theta_max 0.991 _diffrn_measurement_device Area _diffrn_measurement_device_type 'Nonius KappaCCD' _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 46 _diffrn_reflns_limit_h_min -45 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_number 14302 _diffrn_reflns_theta_full 26.652 _diffrn_reflns_theta_max 27.476 _diffrn_reflns_theta_min 5.125 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.101 _exptl_absorpt_correction_T_max 0.98 _exptl_absorpt_correction_T_min 0.98 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.363 _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 1392 _exptl_crystal_size_max 0.280 _exptl_crystal_size_mid 0.200 _exptl_crystal_size_min 0.160 _refine_diff_density_max 0.31 _refine_diff_density_min -0.27 _refine_ls_extinction_method None _refine_ls_goodness_of_fit_ref 0.9509 _refine_ls_hydrogen_treatment none _refine_ls_matrix_type full _refine_ls_number_parameters 217 _refine_ls_number_reflns 3651 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0568 _refine_ls_R_factor_gt 0.0406 _refine_ls_shift/su_max 0.0006677 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details ; Method= Modified Sheldrick w=1/[\s^2^(F^2^) + ( 0.03P)^2^ + 2.78P] ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 ; _refine_ls_weighting_scheme calc _refine_ls_wR_factor_all 0.0969 _refine_ls_wR_factor_gt 0.0891 _refine_ls_wR_factor_ref 0.0969 _reflns_limit_h_max 42 _reflns_limit_h_min -46 _reflns_limit_k_max 8 _reflns_limit_k_min 0 _reflns_limit_l_max 18 _reflns_limit_l_min 0 _reflns_number_gt 2870 _reflns_number_total 3651 _reflns_threshold_expression I>2.0\s(I) _oxford_diffrn_Wilson_B_factor 2.51 _oxford_diffrn_Wilson_scale 6.35 _oxford_refine_ls_r_factor_ref 0.0568 _oxford_refine_ls_scale 0.4148(6) _oxford_reflns_number_all 3651 _oxford_reflns_threshold_expression_ref I>-3.0\s(I) _[local]_cod_data_source_file ol200478p_si_001.cif _[local]_cod_data_source_block 26 _[local]_cod_cif_authors_sg_H-M 'C 1 2/c 1 ' _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 2.4.1 from 2010-06-29. Automatic conversion script Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana ; _cod_original_cell_volume 3219.53(15) _cod_database_code 1502105 _iucr_refine_instruction_details_constraints ; BLOCK SCALE X'S, U'S RIDE C ( 2,X'S) H ( 21,X'S) RIDE C ( 3,X'S) H ( 31,X'S) RIDE C ( 5,X'S) H ( 51,X'S) RIDE C ( 6,X'S) H ( 61,X'S) RIDE C ( 8,X'S) H ( 81,X'S) H ( 82,X'S) RIDE C ( 10,X'S) H ( 101,X'S) H ( 102,X'S) RIDE C ( 11,X'S) H ( 111,X'S) RIDE C ( 12,X'S) H ( 121,X'S) H ( 122,X'S) RIDE C ( 13,X'S) H ( 131,X'S) H ( 132,X'S) H ( 133,X'S) RIDE C ( 17,X'S) H ( 171,X'S) RIDE C ( 18,X'S) H ( 181,X'S) RIDE C ( 23,X'S) H ( 231,X'S) RIDE C ( 24,X'S) H ( 241,X'S) END ; _iucr_refine_instruction_details_restraints ; NO REM HREST START (DO NOT REMOVE THIS LINE) REM HREST END (DO NOT REMOVE THIS LINE) END ; 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 0.62466(3) 0.24213(13) 0.53786(7) 0.0280 1.0000 Uani . C2 C 0.66187(4) 0.12945(18) 0.58770(10) 0.0255 1.0000 Uani . C3 C 0.68276(3) 0.11162(18) 0.51093(9) 0.0236 1.0000 Uani . N4 N 0.65381(3) 0.04791(15) 0.41024(8) 0.0257 1.0000 Uani . C5 C 0.64665(4) -0.14189(19) 0.39355(10) 0.0300 1.0000 Uani . C6 C 0.66811(4) -0.2837(2) 0.45775(11) 0.0336 1.0000 Uani . C7 C 0.70521(4) -0.24129(19) 0.54065(10) 0.0291 1.0000 Uani . C8 C 0.71818(4) -0.03096(19) 0.55054(10) 0.0278 1.0000 Uani . O9 O 0.72760(3) -0.36476(15) 0.59775(8) 0.0395 1.0000 Uani . C10 C 0.63350(4) 0.1892(2) 0.33028(10) 0.0316 1.0000 Uani . C11 C 0.65944(4) 0.2704(2) 0.27763(10) 0.0339 1.0000 Uani . C12 C 0.69680(4) 0.2197(2) 0.29326(11) 0.0363 1.0000 Uani . C13 C 0.68686(4) 0.2404(2) 0.68302(10) 0.0327 1.0000 Uani . C14 C 0.58905(4) 0.1526(2) 0.51007(11) 0.0315 1.0000 Uani . O15 O 0.58434(3) -0.01547(16) 0.52495(10) 0.0537 1.0000 Uani . C16 C 0.55477(4) 0.2887(2) 0.45727(10) 0.0292 1.0000 Uani . C17 C 0.56094(4) 0.4855(2) 0.44928(10) 0.0301 1.0000 Uani . C18 C 0.52809(4) 0.6063(2) 0.40158(10) 0.0316 1.0000 Uani . C19 C 0.48977(4) 0.5253(2) 0.36303(10) 0.0296 1.0000 Uani . N20 N 0.45456(4) 0.65331(18) 0.31462(9) 0.0354 1.0000 Uani . O21 O 0.42074(3) 0.58148(18) 0.28589(9) 0.0509 1.0000 Uani . O22 O 0.46069(3) 0.82478(16) 0.30556(9) 0.0523 1.0000 Uani . C23 C 0.48280(4) 0.3309(2) 0.36951(11) 0.0358 1.0000 Uani . C24 C 0.51587(4) 0.2121(2) 0.41732(12) 0.0364 1.0000 Uani . H21 H 0.6548 -0.0019 0.6046 0.0290 1.0000 Uiso R H31 H 0.6926 0.2425 0.5016 0.0271 1.0000 Uiso R H51 H 0.6241 -0.1774 0.3299 0.0370 1.0000 Uiso R H61 H 0.6590 -0.4173 0.4450 0.0408 1.0000 Uiso R H81 H 0.7347 -0.0159 0.5084 0.0330 1.0000 Uiso R H82 H 0.7350 -0.0030 0.6240 0.0323 1.0000 Uiso R H101 H 0.6232 0.2969 0.3620 0.0371 1.0000 Uiso R H102 H 0.6094 0.1232 0.2775 0.0367 1.0000 Uiso R H111 H 0.6466 0.3698 0.2266 0.0405 1.0000 Uiso R H121 H 0.7111 0.2786 0.2555 0.0453 1.0000 Uiso R H122 H 0.7105 0.1184 0.3441 0.0444 1.0000 Uiso R H131 H 0.7123 0.1694 0.7227 0.0482 1.0000 Uiso R H132 H 0.6938 0.3677 0.6622 0.0478 1.0000 Uiso R H133 H 0.6703 0.2564 0.7249 0.0476 1.0000 Uiso R H171 H 0.5880 0.5365 0.4782 0.0367 1.0000 Uiso R H181 H 0.5313 0.7456 0.3968 0.0354 1.0000 Uiso R H231 H 0.4555 0.2807 0.3397 0.0402 1.0000 Uiso R H241 H 0.5120 0.0743 0.4224 0.0416 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 0.0228(4) 0.0235(5) 0.0379(5) 0.0026(4) 0.0119(4) 0.0044(4) C2 0.0238(6) 0.0217(6) 0.0305(6) 0.0028(5) 0.0096(5) 0.0046(5) C3 0.0215(6) 0.0210(6) 0.0262(6) -0.0016(5) 0.0068(5) -0.0008(5) N4 0.0242(5) 0.0234(5) 0.0257(5) -0.0002(4) 0.0051(4) -0.0007(4) C5 0.0284(7) 0.0282(7) 0.0313(7) -0.0060(5) 0.0088(5) -0.0037(6) C6 0.0385(8) 0.0215(7) 0.0402(8) -0.0042(6) 0.0142(6) -0.0021(6) C7 0.0332(7) 0.0269(7) 0.0313(7) 0.0017(5) 0.0169(6) 0.0089(6) C8 0.0218(6) 0.0292(7) 0.0302(7) -0.0021(5) 0.0074(5) 0.0034(5) O9 0.0450(6) 0.0343(6) 0.0406(6) 0.0085(4) 0.0180(5) 0.0164(5) C10 0.0284(7) 0.0307(7) 0.0303(7) 0.0045(5) 0.0051(5) 0.0034(6) C11 0.0423(8) 0.0285(7) 0.0289(7) 0.0021(5) 0.0113(6) -0.0008(6) C12 0.0416(8) 0.0366(8) 0.0334(7) -0.0031(6) 0.0172(6) -0.0067(7) C13 0.0365(7) 0.0321(7) 0.0291(7) -0.0032(6) 0.0118(6) 0.0022(6) C14 0.0263(7) 0.0268(7) 0.0423(8) 0.0007(6) 0.0141(6) 0.0010(6) O15 0.0305(5) 0.0277(6) 0.0961(9) 0.0130(6) 0.0162(6) 0.0001(4) C16 0.0257(6) 0.0284(7) 0.0348(7) -0.0013(5) 0.0129(5) 0.0023(5) C17 0.0246(6) 0.0285(7) 0.0367(7) -0.0016(6) 0.0110(5) 0.0005(5) C18 0.0304(7) 0.0271(7) 0.0356(7) 0.0007(6) 0.0106(6) 0.0032(6) C19 0.0263(6) 0.0331(7) 0.0273(6) -0.0003(5) 0.0078(5) 0.0068(6) N20 0.0302(6) 0.0388(7) 0.0321(6) 0.0018(5) 0.0060(5) 0.0072(5) O21 0.0257(5) 0.0550(8) 0.0602(7) 0.0121(6) 0.0029(5) 0.0042(5) O22 0.0409(6) 0.0338(6) 0.0669(8) 0.0043(5) 0.0033(5) 0.0090(5) C23 0.0251(6) 0.0365(8) 0.0406(8) -0.0037(6) 0.0067(6) -0.0015(6) C24 0.0285(7) 0.0279(7) 0.0504(8) -0.0019(6) 0.0121(6) -0.0008(6) 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' 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' 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' 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 C14 118.82(10) yes O1 C2 C3 107.28(9) yes O1 C2 C13 106.11(10) yes C3 C2 C13 112.88(10) yes O1 C2 H21 109.6 no C3 C2 H21 109.3 no C13 C2 H21 111.6 no C2 C3 N4 110.77(10) yes C2 C3 C8 110.37(10) yes N4 C3 C8 109.82(10) yes C2 C3 H31 108.0 no N4 C3 H31 107.3 no C8 C3 H31 110.5 no C3 N4 C5 118.68(10) yes C3 N4 C10 120.39(10) yes C5 N4 C10 120.93(11) yes N4 C5 C6 124.67(12) yes N4 C5 H51 116.1 no C6 C5 H51 119.2 no C5 C6 C7 120.77(13) yes C5 C6 H61 119.9 no C7 C6 H61 119.2 no C6 C7 C8 115.39(11) yes C6 C7 O9 124.17(13) yes C8 C7 O9 120.25(12) yes C3 C8 C7 113.81(10) yes C3 C8 H81 108.1 no C7 C8 H81 106.0 no C3 C8 H82 110.0 no C7 C8 H82 108.8 no H81 C8 H82 110.0 no N4 C10 C11 114.52(11) yes N4 C10 H101 108.0 no C11 C10 H101 110.0 no N4 C10 H102 107.6 no C11 C10 H102 108.6 no H101 C10 H102 108.0 no C10 C11 C12 126.46(13) yes C10 C11 H111 115.3 no C12 C11 H111 118.3 no C11 C12 H121 120.9 no C11 C12 H122 120.1 no H121 C12 H122 119.0 no C2 C13 H131 110.7 no C2 C13 H132 108.5 no H131 C13 H132 109.3 no C2 C13 H133 107.8 no H131 C13 H133 110.0 no H132 C13 H133 110.6 no O1 C14 O15 125.32(12) yes O1 C14 C16 111.20(11) yes O15 C14 C16 123.48(12) yes C14 C16 C17 122.07(12) yes C14 C16 C24 117.58(12) yes C17 C16 C24 120.34(12) yes C16 C17 C18 119.89(12) yes C16 C17 H171 119.3 no C18 C17 H171 120.8 no C17 C18 C19 118.27(13) yes C17 C18 H181 121.9 no C19 C18 H181 119.8 no C18 C19 N20 118.67(12) yes C18 C19 C23 123.05(12) yes N20 C19 C23 118.26(12) yes C19 N20 O21 117.96(12) yes C19 N20 O22 118.46(12) yes O21 N20 O22 123.57(12) yes C19 C23 C24 118.05(13) yes C19 C23 H231 119.9 no C24 C23 H231 122.0 no C16 C24 C23 120.39(13) yes C16 C24 H241 119.6 no C23 C24 H241 120.0 no loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag O1 C2 1.4682(14) yes O1 C14 1.3311(15) yes C2 C3 1.5339(17) yes C2 C13 1.5108(18) yes C2 H21 0.995 no C3 N4 1.4716(15) yes C3 C8 1.5314(17) yes C3 H31 0.997 no N4 C5 1.3413(17) yes N4 C10 1.4607(16) yes C5 C6 1.3578(19) yes C5 H51 0.983 no C6 C7 1.425(2) yes C6 H61 0.973 no C7 C8 1.5172(19) yes C7 O9 1.2363(16) yes C8 H81 0.989 no C8 H82 0.999 no C10 C11 1.4976(19) yes C10 H101 1.007 no C10 H102 1.009 no C11 C12 1.313(2) yes C11 H111 0.975 no C12 H121 0.957 no C12 H122 0.989 no C13 H131 0.996 no C13 H132 0.989 no C13 H133 0.986 no C14 O15 1.2047(17) yes C14 C16 1.4985(18) yes C16 C17 1.3906(19) yes C16 C24 1.3892(19) yes C17 C18 1.3877(19) yes C17 H171 0.960 no C18 C19 1.3832(19) yes C18 H181 0.976 no C19 N20 1.4753(17) yes C19 C23 1.377(2) yes N20 O21 1.2227(16) yes N20 O22 1.2217(16) yes C23 C24 1.385(2) yes C23 H231 0.968 no C24 H241 0.970 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 C5 H51 O21 5_645 151 0.98 2.45 3.352(2) yes C8 H81 O9 4_646 155 0.99 2.50 3.419(2) yes C12 H121 O9 6_554 157 0.96 2.58 3.480(2) yes C13 H132 O9 1_565 163 0.99 2.56 3.513(2) yes C24 H241 O22 1_545 134 0.97 2.60 3.344(2) yes _journal_paper_doi 10.1021/ol200478p