#------------------------------------------------------------------------------ #$Date: 2012-02-26 04:29:20 +0200 (Sun, 26 Feb 2012) $ #$Revision: 35486 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/1502171.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_1502171 loop_ _publ_author_name 'Luan, Yi' 'Schaus, Scott E.' _publ_section_title ; Multicomponent Mannich reactions with boron enolates derived from diazo esters and 9-BBN. ; _journal_issue 9 _journal_name_full 'Organic letters' _journal_page_first 2510 _journal_page_last 2513 _journal_volume 13 _journal_year 2011 _chemical_absolute_configuration rm _chemical_formula_moiety 'C38 H39 N O3' _chemical_formula_sum 'C38 H39 N O3' _chemical_formula_weight 557.70 _chemical_name_systematic ; ? ; _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 direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-97 _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 10.3359(6) _cell_length_b 14.8610(10) _cell_length_c 19.5709(11) _cell_measurement_reflns_used 3128 _cell_measurement_temperature 173(2) _cell_measurement_theta_max 23.31 _cell_measurement_theta_min 2.49 _cell_volume 3006.1(3) _computing_cell_refinement 'Bruker SAINT+' _computing_data_collection 'Bruker APEX2' _computing_data_reduction 'Bruker SAINT+' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _diffrn_ambient_temperature 173(2) _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_device_type 'Bruker X8 APEX II diffractometer' _diffrn_measurement_method 'phi and omega scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0472 _diffrn_reflns_av_sigmaI/netI 0.0530 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_number 16060 _diffrn_reflns_theta_full 28.30 _diffrn_reflns_theta_max 28.30 _diffrn_reflns_theta_min 2.23 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.077 _exptl_absorpt_correction_T_max 0.9885 _exptl_absorpt_correction_T_min 0.9553 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details SADABS _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.232 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 1192 _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.15 _refine_diff_density_max 0.175 _refine_diff_density_min -0.175 _refine_diff_density_rms 0.039 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.004 _refine_ls_hydrogen_treatment refall _refine_ls_matrix_type full _refine_ls_number_parameters 535 _refine_ls_number_reflns 4162 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.004 _refine_ls_R_factor_all 0.0665 _refine_ls_R_factor_gt 0.0437 _refine_ls_shift/su_max 0.015 _refine_ls_shift/su_mean 0.001 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0456P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0840 _refine_ls_wR_factor_ref 0.0929 _reflns_number_gt 3121 _reflns_number_total 4162 _reflns_threshold_expression >2sigma(I) _[local]_cod_data_source_file ol200766t_si_002.cif _[local]_cod_data_source_block schaus24 _[local]_cod_cif_authors_sg_H-M P2(1)2(1)2(1) _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 2.4.1 from 2010-06-29. Automatic conversion script Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana ; _cod_database_code 1502171 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' 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_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag O1 O 0.01065(11) 0.01386(8) 0.16300(5) 0.0233(3) Uani 1 1 d O2 O -0.06726(13) -0.08574(8) 0.23861(6) 0.0344(3) Uani 1 1 d O3 O 0.31925(16) 0.28650(11) 0.34490(8) 0.0587(5) Uani 1 1 d N1 N 0.16586(15) 0.18196(10) 0.30613(8) 0.0324(4) Uani 1 1 d C1 C -0.02326(17) -0.04648(12) 0.10574(8) 0.0246(4) Uani 1 1 d H1 H -0.1030(16) -0.0777(13) 0.1198(8) 0.027(5) Uiso 1 1 d C2 C 0.08570(19) -0.11377(13) 0.09845(9) 0.0282(4) Uani 1 1 d H2B H 0.1717(17) -0.0808(12) 0.0899(8) 0.023(5) Uiso 1 1 d H2A H 0.0969(17) -0.1464(13) 0.1391(9) 0.032(5) Uiso 1 1 d C3 C 0.06982(18) -0.17782(12) 0.03818(9) 0.0282(4) Uani 1 1 d H3 H -0.0086(16) -0.2109(12) 0.0416(9) 0.027(5) Uiso 1 1 d C4 C 0.0542(2) -0.12229(13) -0.02642(9) 0.0327(5) Uani 1 1 d H4B H 0.1401(19) -0.0912(13) -0.0331(10) 0.043(6) Uiso 1 1 d H4A H 0.0395(18) -0.1607(14) -0.0657(10) 0.043(6) Uiso 1 1 d C5 C -0.0568(2) -0.05546(13) -0.01925(9) 0.0327(5) Uani 1 1 d H5A H -0.138(2) -0.0895(14) -0.0130(10) 0.044(6) Uiso 1 1 d H5 H -0.0657(16) -0.0182(13) -0.0584(9) 0.030(5) Uiso 1 1 d C6 C -0.04111(17) 0.01026(12) 0.04144(8) 0.0241(4) Uani 1 1 d H6 H 0.0435(16) 0.0456(12) 0.0340(8) 0.022(4) Uiso 1 1 d C7 C -0.15486(18) 0.08016(13) 0.04154(9) 0.0294(4) Uani 1 1 d C8 C -0.14816(18) 0.13385(12) -0.02550(9) 0.0283(4) Uani 1 1 d C9 C -0.24595(19) 0.13205(14) -0.07438(10) 0.0363(5) Uani 1 1 d H9 H -0.3249(17) 0.0950(12) -0.0673(9) 0.030(5) Uiso 1 1 d C10 C -0.2379(2) 0.18280(15) -0.13392(11) 0.0451(6) Uani 1 1 d H10 H -0.312(2) 0.1818(16) -0.1650(11) 0.056(7) Uiso 1 1 d C11 C -0.1322(2) 0.23609(14) -0.14601(10) 0.0439(6) Uani 1 1 d H11 H -0.1225(18) 0.2707(14) -0.1872(10) 0.042(6) Uiso 1 1 d C12 C -0.0340(2) 0.23949(14) -0.09817(11) 0.0417(5) Uani 1 1 d H12 H 0.043(2) 0.2741(17) -0.1062(11) 0.060(7) Uiso 1 1 d C13 C -0.0423(2) 0.18901(13) -0.03912(10) 0.0348(5) Uani 1 1 d H13 H 0.0289(18) 0.1893(12) -0.0071(10) 0.038(5) Uiso 1 1 d C14 C -0.1456(2) 0.14823(15) 0.10032(10) 0.0426(6) Uani 1 1 d H14 H -0.0516(17) 0.1757(12) 0.0967(9) 0.025(5) Uiso 1 1 d H14B H -0.168(2) 0.1187(16) 0.1446(11) 0.055(6) Uiso 1 1 d H14A H -0.215(2) 0.1980(15) 0.0932(11) 0.058(7) Uiso 1 1 d C15 C -0.2857(2) 0.03252(17) 0.04997(12) 0.0461(6) Uani 1 1 d H15C H -0.288(2) 0.0013(16) 0.0928(12) 0.062(7) Uiso 1 1 d H15B H -0.305(2) -0.0133(15) 0.0126(11) 0.059(7) Uiso 1 1 d H15A H -0.363(2) 0.0766(15) 0.0514(10) 0.048(6) Uiso 1 1 d C16 C 0.1833(2) -0.24294(13) 0.03288(10) 0.0356(5) Uani 1 1 d H16C H 0.269(2) -0.2076(13) 0.0245(10) 0.043(6) Uiso 1 1 d H16B H 0.195(2) -0.2763(15) 0.0738(11) 0.047(6) Uiso 1 1 d H16A H 0.167(2) -0.2828(14) -0.0064(11) 0.047(6) Uiso 1 1 d C17 C -0.01616(16) -0.01505(12) 0.22649(8) 0.0242(4) Uani 1 1 d C18 C 0.01711(17) 0.05704(12) 0.28054(8) 0.0230(4) Uani 1 1 d C19 C 0.14262(17) 0.10886(11) 0.25780(9) 0.0245(4) Uani 1 1 d H19 H 0.1257(15) 0.1373(11) 0.2126(8) 0.018(4) Uiso 1 1 d C20 C 0.26151(16) 0.04971(12) 0.25074(9) 0.0253(4) Uani 1 1 d C21 C 0.31013(17) 0.03082(13) 0.18624(9) 0.0299(5) Uani 1 1 d H21 H 0.2663(16) 0.0568(11) 0.1453(9) 0.021(4) Uiso 1 1 d C22 C 0.41862(18) -0.02250(15) 0.17843(10) 0.0369(5) Uani 1 1 d H22 H 0.4490(17) -0.0348(13) 0.1330(9) 0.030(5) Uiso 1 1 d C23 C 0.48020(19) -0.05849(14) 0.23424(11) 0.0392(5) Uani 1 1 d H23 H 0.5572(19) -0.0955(14) 0.2279(10) 0.038(6) Uiso 1 1 d C24 C 0.43352(18) -0.03926(14) 0.29904(10) 0.0356(5) Uani 1 1 d H24 H 0.4768(17) -0.0620(13) 0.3387(9) 0.032(5) Uiso 1 1 d C25 C 0.32670(17) 0.01496(13) 0.30728(9) 0.0305(4) Uani 1 1 d H25 H 0.2936(16) 0.0249(12) 0.3510(9) 0.028(5) Uiso 1 1 d C26 C 0.03832(16) 0.01742(12) 0.35202(9) 0.0244(4) Uani 1 1 d C27 C 0.07783(18) -0.07067(13) 0.36418(9) 0.0300(5) Uani 1 1 d H27 H 0.0819(17) -0.1133(13) 0.3263(9) 0.031(5) Uiso 1 1 d C28 C 0.1114(2) -0.09847(15) 0.42951(10) 0.0381(5) Uani 1 1 d H28 H 0.139(2) -0.1609(16) 0.4387(11) 0.055(7) Uiso 1 1 d C29 C 0.1063(2) -0.03965(15) 0.48363(10) 0.0395(5) Uani 1 1 d H29 H 0.1314(19) -0.0577(14) 0.5299(10) 0.043(6) Uiso 1 1 d C30 C 0.06460(19) 0.04717(15) 0.47280(10) 0.0363(5) Uani 1 1 d H30 H 0.060(2) 0.0886(14) 0.5110(11) 0.049(6) Uiso 1 1 d C31 C 0.03006(18) 0.07525(13) 0.40803(9) 0.0284(4) Uani 1 1 d H31 H 0.0012(16) 0.1353(12) 0.4010(8) 0.019(4) Uiso 1 1 d C32 C -0.10472(17) 0.11826(12) 0.28118(8) 0.0227(4) Uani 1 1 d C33 C -0.22106(18) 0.08035(13) 0.30237(10) 0.0291(4) Uani 1 1 d H33 H -0.2199(17) 0.0236(13) 0.3158(9) 0.032(5) Uiso 1 1 d C34 C -0.33419(18) 0.12889(14) 0.30297(10) 0.0348(5) Uani 1 1 d H34 H -0.4161(19) 0.1001(13) 0.3188(10) 0.038(5) Uiso 1 1 d C35 C -0.33439(19) 0.21810(14) 0.28208(10) 0.0329(5) Uani 1 1 d H35 H -0.4141(19) 0.2556(13) 0.2836(9) 0.031(5) Uiso 1 1 d C36 C -0.22073(18) 0.25712(13) 0.26093(9) 0.0298(4) Uani 1 1 d H36 H -0.2238(17) 0.3227(12) 0.2470(9) 0.026(5) Uiso 1 1 d C37 C -0.10610(18) 0.20791(12) 0.26049(9) 0.0263(4) Uani 1 1 d H37 H -0.0276(18) 0.2385(13) 0.2485(10) 0.033(5) Uiso 1 1 d C38 C 0.2468(2) 0.23271(14) 0.32300(9) 0.0332(5) Uani 1 1 d 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 0.0302(6) 0.0217(6) 0.0180(6) -0.0007(5) 0.0001(5) -0.0027(5) O2 0.0528(8) 0.0253(6) 0.0250(6) -0.0019(6) 0.0045(6) -0.0110(6) O3 0.0637(9) 0.0588(10) 0.0538(9) -0.0041(8) -0.0105(8) -0.0319(9) N1 0.0324(8) 0.0284(8) 0.0364(9) -0.0091(7) 0.0051(7) -0.0063(7) C1 0.0312(9) 0.0226(9) 0.0201(8) -0.0015(7) -0.0005(8) -0.0019(8) C2 0.0360(10) 0.0274(10) 0.0212(9) 0.0035(8) -0.0018(8) 0.0023(9) C3 0.0358(10) 0.0237(9) 0.0253(9) 0.0002(8) 0.0014(8) -0.0007(8) C4 0.0451(11) 0.0301(10) 0.0229(9) -0.0029(8) 0.0021(9) 0.0067(9) C5 0.0450(11) 0.0300(10) 0.0231(9) 0.0005(8) -0.0067(8) 0.0022(10) C6 0.0295(9) 0.0225(9) 0.0203(8) -0.0002(7) -0.0021(7) 0.0003(8) C7 0.0347(9) 0.0281(9) 0.0253(9) 0.0010(8) -0.0022(8) 0.0051(9) C8 0.0346(10) 0.0230(9) 0.0272(9) -0.0053(8) -0.0078(8) 0.0061(8) C9 0.0367(11) 0.0342(11) 0.0380(11) -0.0006(9) -0.0120(9) 0.0031(10) C10 0.0574(13) 0.0411(12) 0.0368(11) -0.0012(10) -0.0199(10) 0.0113(12) C11 0.0709(15) 0.0302(10) 0.0305(10) 0.0073(9) -0.0045(11) 0.0081(11) C12 0.0531(13) 0.0283(10) 0.0437(12) 0.0023(10) -0.0012(10) -0.0035(11) C13 0.0400(11) 0.0310(10) 0.0334(10) 0.0013(9) -0.0098(9) 0.0003(9) C14 0.0607(14) 0.0373(12) 0.0297(10) -0.0018(9) 0.0004(11) 0.0188(12) C15 0.0336(11) 0.0522(14) 0.0526(14) 0.0111(12) 0.0026(10) 0.0056(11) C16 0.0458(12) 0.0281(10) 0.0330(10) -0.0002(9) 0.0052(10) 0.0075(9) C17 0.0270(9) 0.0218(9) 0.0239(9) -0.0010(8) 0.0028(7) -0.0009(8) C18 0.0292(9) 0.0193(8) 0.0205(8) 0.0004(7) 0.0023(7) -0.0014(8) C19 0.0326(9) 0.0206(9) 0.0203(8) -0.0035(7) 0.0030(8) -0.0036(8) C20 0.0270(8) 0.0234(8) 0.0256(9) -0.0037(8) 0.0020(8) -0.0048(8) C21 0.0280(9) 0.0343(11) 0.0275(9) -0.0009(9) 0.0025(8) -0.0041(9) C22 0.0329(10) 0.0451(12) 0.0326(10) -0.0151(10) 0.0076(8) -0.0039(10) C23 0.0304(10) 0.0332(11) 0.0542(13) -0.0129(10) -0.0003(10) 0.0027(9) C24 0.0329(10) 0.0346(11) 0.0393(11) 0.0006(10) -0.0058(9) -0.0066(9) C25 0.0292(9) 0.0354(10) 0.0267(9) -0.0023(9) 0.0040(8) -0.0063(9) C26 0.0256(8) 0.0268(9) 0.0208(8) 0.0003(8) 0.0038(7) -0.0027(8) C27 0.0347(10) 0.0274(10) 0.0278(9) 0.0017(8) 0.0060(8) 0.0021(9) C28 0.0410(11) 0.0375(12) 0.0358(11) 0.0108(9) 0.0003(10) 0.0039(10) C29 0.0422(11) 0.0495(13) 0.0266(10) 0.0068(10) -0.0033(9) -0.0003(11) C30 0.0398(11) 0.0443(12) 0.0248(10) -0.0034(10) -0.0004(9) -0.0062(10) C31 0.0324(10) 0.0269(10) 0.0259(10) -0.0017(8) 0.0020(8) -0.0019(9) C32 0.0289(9) 0.0220(9) 0.0171(8) -0.0030(7) 0.0000(7) -0.0006(8) C33 0.0331(10) 0.0229(9) 0.0311(10) 0.0000(8) 0.0005(8) -0.0052(9) C34 0.0270(9) 0.0342(11) 0.0433(11) -0.0001(10) 0.0025(9) -0.0050(9) C35 0.0281(9) 0.0325(10) 0.0380(11) -0.0037(9) -0.0003(9) 0.0022(9) C36 0.0360(10) 0.0244(9) 0.0292(9) 0.0002(8) -0.0002(8) 0.0000(8) C37 0.0308(9) 0.0234(9) 0.0247(9) -0.0006(8) 0.0047(8) -0.0015(8) C38 0.0391(11) 0.0318(10) 0.0288(10) 0.0037(9) 0.0013(9) -0.0051(10) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 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 C17 O1 C1 117.28(13) C38 N1 C19 141.01(17) O1 C1 C2 107.22(13) O1 C1 C6 108.59(14) C2 C1 C6 112.18(14) C1 C2 C3 113.92(15) C4 C3 C16 111.75(15) C4 C3 C2 108.44(15) C16 C3 C2 111.49(16) C3 C4 C5 110.97(15) C4 C5 C6 113.81(15) C1 C6 C5 107.29(14) C1 C6 C7 117.10(14) C5 C6 C7 109.92(14) C14 C7 C15 106.15(17) C14 C7 C8 107.14(15) C15 C7 C8 111.76(16) C14 C7 C6 112.99(15) C15 C7 C6 110.79(16) C8 C7 C6 108.00(14) C9 C8 C13 116.75(17) C9 C8 C7 122.95(17) C13 C8 C7 120.28(16) C10 C9 C8 121.5(2) C11 C10 C9 120.4(2) C10 C11 C12 119.32(19) C11 C12 C13 120.1(2) C12 C13 C8 121.92(19) O2 C17 O1 123.62(15) O2 C17 C18 124.76(15) O1 C17 C18 111.45(14) C26 C18 C17 112.97(14) C26 C18 C32 109.48(13) C17 C18 C32 103.37(13) C26 C18 C19 109.16(14) C17 C18 C19 109.24(13) C32 C18 C19 112.58(14) N1 C19 C20 110.90(14) N1 C19 C18 108.46(14) C20 C19 C18 114.21(14) C21 C20 C25 118.16(16) C21 C20 C19 119.57(16) C25 C20 C19 122.26(15) C22 C21 C20 120.71(17) C23 C22 C21 120.79(18) C22 C23 C24 119.08(18) C25 C24 C23 120.45(18) C24 C25 C20 120.76(17) C27 C26 C31 117.57(16) C27 C26 C18 124.00(16) C31 C26 C18 118.12(16) C28 C27 C26 120.73(18) C29 C28 C27 120.7(2) C30 C29 C28 119.32(18) C29 C30 C31 120.34(18) C30 C31 C26 121.26(18) C37 C32 C33 117.73(17) C37 C32 C18 124.49(16) C33 C32 C18 117.77(15) C34 C33 C32 121.71(18) C33 C34 C35 120.03(18) C36 C35 C34 119.39(18) C35 C36 C37 120.51(17) C36 C37 C32 120.63(17) O3 C38 N1 173.2(2) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance O1 C17 1.3437(19) O1 C1 1.477(2) O2 C17 1.199(2) O3 C38 1.176(2) N1 C38 1.174(2) N1 C19 1.460(2) C1 C2 1.513(3) C1 C6 1.526(2) C2 C3 1.525(3) C3 C4 1.518(3) C3 C16 1.524(3) C4 C5 1.523(3) C5 C6 1.546(2) C6 C7 1.569(2) C7 C14 1.535(3) C7 C15 1.536(3) C7 C8 1.537(2) C8 C9 1.392(3) C8 C13 1.393(3) C9 C10 1.391(3) C10 C11 1.370(3) C11 C12 1.382(3) C12 C13 1.380(3) C17 C18 1.544(2) C18 C26 1.533(2) C18 C32 1.554(2) C18 C19 1.573(2) C19 C20 1.517(2) C20 C21 1.387(2) C20 C25 1.395(2) C21 C22 1.381(3) C22 C23 1.373(3) C23 C24 1.387(3) C24 C25 1.376(3) C26 C27 1.392(3) C26 C31 1.396(2) C27 C28 1.388(3) C28 C29 1.374(3) C29 C30 1.377(3) C30 C31 1.382(3) C32 C37 1.393(2) C32 C33 1.391(3) C33 C34 1.374(3) C34 C35 1.387(3) C35 C36 1.374(3) C36 C37 1.392(3)