#------------------------------------------------------------------------------ #$Date: 2013-12-28 09:07:06 +0200 (Sat, 28 Dec 2013) $ #$Revision: 91932 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/50/83/1508362.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_1508362 loop_ _publ_author_name 'Brock, E. Anne' 'Davies, Stephen G.' 'Lee, James A.' 'Roberts, Paul M.' 'Thomson, James E.' _publ_section_title ; Asymmetric Synthesis of the Tropane Alkaloid (+)-Pseudococaine via Ring-Closing Iodoamination. ; _journal_issue 16 _journal_name_full 'Organic letters' _journal_page_first 4278 _journal_page_last 4281 _journal_volume 14 _journal_year 2012 _chemical_absolute_configuration unk _chemical_formula_moiety 'C10 H17 N1 O3' _chemical_formula_sum 'C10 H17 N O3' _chemical_formula_weight 199.25 _space_group_IT_number 19 _symmetry_cell_setting orthorhombic _symmetry_space_group_name_Hall 'P 2ac 2ab' _symmetry_space_group_name_H-M 'P 21 21 21' _atom_sites_solution_hydrogens difmap _atom_sites_solution_primary other _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 6.3402(2) _cell_length_b 8.2496(3) _cell_length_c 18.8623(6) _cell_measurement_reflns_used 1281 _cell_measurement_temperature 150 _cell_measurement_theta_max 27 _cell_measurement_theta_min 5 _cell_volume 986.58(6) _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 'USER DEFINED STRUCTURE SOLUTION' _diffrn_ambient_temperature 150 _diffrn_measured_fraction_theta_full 0.988 _diffrn_measured_fraction_theta_max 0.988 _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 0.024 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_number 2242 _diffrn_reflns_theta_full 25.546 _diffrn_reflns_theta_max 27.469 _diffrn_reflns_theta_min 5.193 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.098 _exptl_absorpt_correction_T_max 0.99 _exptl_absorpt_correction_T_min 0.99 _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_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 432 _exptl_crystal_size_max 0.250 _exptl_crystal_size_mid 0.130 _exptl_crystal_size_min 0.110 _refine_diff_density_max 0.34 _refine_diff_density_min -0.26 _refine_ls_extinction_method None _refine_ls_goodness_of_fit_ref 0.9422 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 127 _refine_ls_number_reflns 1323 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0478 _refine_ls_R_factor_gt 0.0383 _refine_ls_shift/su_max 0.0001577 _refine_ls_shift/su_mean 0.0000185 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details ; Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ A~i~ are: 17.7 26.2 13.3 3.77 ; _refine_ls_weighting_scheme calc _refine_ls_wR_factor_all 0.1050 _refine_ls_wR_factor_gt 0.0930 _refine_ls_wR_factor_ref 0.1050 _reflns_limit_h_max 8 _reflns_limit_h_min 0 _reflns_limit_k_max 10 _reflns_limit_k_min 0 _reflns_limit_l_max 24 _reflns_limit_l_min 0 _reflns_number_gt 1142 _reflns_number_total 1323 _reflns_threshold_expression I>2.0\s(I) _oxford_diffrn_Wilson_B_factor 0.00 _oxford_diffrn_Wilson_scale 0.00 _oxford_refine_ls_r_factor_ref 0.0478 _oxford_refine_ls_scale 0.843(4) _oxford_reflns_number_all 1323 _oxford_reflns_threshold_expression_ref I>-3.0\s(I) _[local]_cod_data_source_file ol3020607_si_002.cif _[local]_cod_data_source_block 22 _[local]_cod_chemical_formula_sum_orig 'C10 H17 N1 O3' _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic' according to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26. '_atom_sites_solution_primary' value 'Other' changed to 'other' 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 1891 2012-01-12 08:04:46Z andrius ; _cod_database_code 1508362 loop_ _symmetry_equiv_pos_as_xyz x,y,z x+1/2,-y+1/2,-z -x,y+1/2,-z+1/2 -x+1/2,-y,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 0.8016(3) 0.5927(2) 0.27365(9) 0.0270 1.0000 Uani . C2 C 0.7770(4) 0.4492(2) 0.31449(12) 0.0213 1.0000 Uani . C3 C 0.9842(3) 0.3938(3) 0.34894(11) 0.0183 1.0000 Uani . C4 C 1.0695(4) 0.5228(3) 0.39819(11) 0.0216 1.0000 Uani . O5 O 1.2712(3) 0.5579(2) 0.38308(9) 0.0270 1.0000 Uani . C6 C 1.3757(4) 0.6754(3) 0.42815(14) 0.0330 1.0000 Uani . O7 O 0.9730(3) 0.5857(2) 0.44590(10) 0.0367 1.0000 Uani . C8 C 0.9487(4) 0.2319(3) 0.38940(11) 0.0202 1.0000 Uani . N9 N 0.8949(3) 0.1083(2) 0.33539(10) 0.0217 1.0000 Uani . C10 C 0.9053(5) -0.0559(3) 0.36595(14) 0.0306 1.0000 Uani . C11 C 0.6745(4) 0.1539(3) 0.31822(13) 0.0263 1.0000 Uani . C12 C 0.6810(4) 0.3079(3) 0.27310(13) 0.0277 1.0000 Uani . C13 C 0.5689(4) 0.1853(3) 0.39117(15) 0.0335 1.0000 Uani . C14 C 0.7539(4) 0.2377(3) 0.43895(12) 0.0288 1.0000 Uani . H21 H 0.6794 0.4760 0.3547 0.0264 1.0000 Uiso R H31 H 1.0875 0.3739 0.3102 0.0243 1.0000 Uiso R H62 H 1.4978 0.7177 0.4022 0.0555 1.0000 Uiso R H61 H 1.4226 0.6207 0.4708 0.0553 1.0000 Uiso R H63 H 1.2787 0.7619 0.4397 0.0552 1.0000 Uiso R H81 H 1.0776 0.2016 0.4171 0.0255 1.0000 Uiso R H102 H 0.8592 -0.1390 0.3319 0.0483 1.0000 Uiso R H101 H 1.0488 -0.0797 0.3808 0.0486 1.0000 Uiso R H103 H 0.8139 -0.0595 0.4086 0.0480 1.0000 Uiso R H111 H 0.6018 0.0646 0.2918 0.0325 1.0000 Uiso R H122 H 0.7653 0.2868 0.2305 0.0364 1.0000 Uiso R H121 H 0.5312 0.3366 0.2581 0.0351 1.0000 Uiso R H132 H 0.5023 0.0839 0.4100 0.0408 1.0000 Uiso R H131 H 0.4611 0.2738 0.3868 0.0407 1.0000 Uiso R H142 H 0.7714 0.1569 0.4781 0.0370 1.0000 Uiso R H141 H 0.7320 0.3503 0.4560 0.0369 1.0000 Uiso R H11 H 0.8989 0.5812 0.2423 0.0433 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 0.0301(8) 0.0184(7) 0.0326(8) 0.0056(7) 0.0016(7) 0.0041(7) C2 0.0205(10) 0.0180(9) 0.0255(10) 0.0007(9) -0.0016(9) 0.0009(9) C3 0.0183(9) 0.0173(9) 0.0194(9) -0.0028(8) 0.0005(8) 0.0005(8) C4 0.0231(10) 0.0186(10) 0.0232(10) -0.0013(8) -0.0012(9) -0.0003(9) O5 0.0222(8) 0.0251(8) 0.0338(8) -0.0083(7) -0.0016(7) -0.0046(7) C6 0.0298(12) 0.0273(12) 0.0419(13) -0.0060(11) -0.0100(11) -0.0065(11) O7 0.0392(10) 0.0359(10) 0.0350(9) -0.0180(8) 0.0110(8) -0.0075(9) C8 0.0224(10) 0.0189(10) 0.0194(9) 0.0005(8) -0.0014(8) -0.0008(9) N9 0.0230(9) 0.0171(8) 0.0251(9) -0.0007(7) -0.0015(8) -0.0009(8) C10 0.0373(13) 0.0167(10) 0.0379(13) 0.0013(10) -0.0007(11) 0.0025(10) C11 0.0224(11) 0.0205(10) 0.0359(12) 0.0006(10) -0.0075(10) -0.003(1) C12 0.0269(10) 0.0230(10) 0.0333(12) 0.0009(10) -0.0102(10) -0.0019(10) C13 0.0231(11) 0.0273(12) 0.0500(15) 0.0047(12) 0.0077(11) -0.0022(10) C14 0.0344(12) 0.0232(10) 0.0287(11) -0.0003(10) 0.0111(10) 0.0010(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 C2 O1 H11 111.0 no O1 C2 C3 112.54(18) yes O1 C2 C12 113.72(18) yes C3 C2 C12 109.26(18) yes O1 C2 H21 107.1 no C3 C2 H21 105.9 no C12 C2 H21 108.0 no C2 C3 C4 110.90(17) yes C2 C3 C8 109.84(17) yes C4 C3 C8 110.78(17) yes C2 C3 H31 107.5 no C4 C3 H31 109.4 no C8 C3 H31 108.3 no C3 C4 O5 111.23(19) yes C3 C4 O7 125.4(2) yes O5 C4 O7 123.3(2) yes C4 O5 C6 117.08(19) yes O5 C6 H62 107.9 no O5 C6 H61 108.4 no H62 C6 H61 109.7 no O5 C6 H63 109.6 no H62 C6 H63 110.6 no H61 C6 H63 110.6 no C3 C8 N9 106.71(16) yes C3 C8 C14 112.64(18) yes N9 C8 C14 104.63(17) yes C3 C8 H81 110.6 no N9 C8 H81 112.0 no C14 C8 H81 110.0 no C8 N9 C10 110.71(17) yes C8 N9 C11 101.09(18) yes C10 N9 C11 111.16(19) yes N9 C10 H102 111.8 no N9 C10 H101 109.9 no H102 C10 H101 109.0 no N9 C10 H103 108.6 no H102 C10 H103 109.5 no H101 C10 H103 107.9 no N9 C11 C12 107.88(19) yes N9 C11 C13 104.79(19) yes C12 C11 C13 111.5(2) yes N9 C11 H111 110.8 no C12 C11 H111 110.3 no C13 C11 H111 111.4 no C11 C12 C2 111.09(18) yes C11 C12 H122 108.8 no C2 C12 H122 109.6 no C11 C12 H121 108.9 no C2 C12 H121 109.6 no H122 C12 H121 108.7 no C11 C13 C14 103.71(19) yes C11 C13 H132 110.9 no C14 C13 H132 110.4 no C11 C13 H131 110.1 no C14 C13 H131 111.2 no H132 C13 H131 110.4 no C13 C14 C8 104.19(17) yes C13 C14 H142 109.2 no C8 C14 H142 109.6 no C13 C14 H141 110.2 no C8 C14 H141 109.6 no H142 C14 H141 113.5 no loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag O1 C2 1.421(3) yes O1 H11 0.859 no C2 C3 1.535(3) yes C2 C12 1.529(3) yes C2 H21 1.003 no C3 C4 1.512(3) yes C3 C8 1.555(3) yes C3 H31 0.995 no C4 O5 1.342(3) yes C4 O7 1.206(3) yes O5 C6 1.450(3) yes C6 H62 0.980 no C6 H61 0.969 no C6 H63 0.967 no C8 N9 1.482(3) yes C8 C14 1.550(3) yes C8 H81 1.002 no N9 C10 1.473(3) yes N9 C11 1.483(3) yes C10 H102 0.984 no C10 H101 0.973 no C10 H103 0.991 no C11 C12 1.530(3) yes C11 C13 1.552(4) yes C11 H111 1.001 no C12 H122 0.980 no C12 H121 1.019 no C13 C14 1.541(4) yes C13 H132 1.002 no C13 H131 1.004 no C14 H142 1.001 no C14 H141 0.992 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 C10 H102 O1 1_545 161.42(7) 0.984 2.498 3.445(3) yes C14 H141 O7 . 128.45(7) 0.992 2.478 3.191(3) yes O1 H11 N9 3_755 166.39(7) 0.859 1.977 2.819(3) yes _journal_paper_doi 10.1021/ol3020607