#------------------------------------------------------------------------------ #$Date: 2017-10-13 00:32:00 +0100 (Fri, 13 Oct 2017) $ #$Revision: 201954 $ #$URL: svn://www.crystallography.net/cod/cif/1/50/78/1507838.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_1507838 loop_ _publ_author_name 'Nakamura, Shuichi' 'Maeno, Yuri' 'Ohara, Mutsuyo' 'Yamamura, Akiko' 'Funahashi, Yasuhiro' 'Shibata, Norio' _publ_section_title ; Enantioselective synthesis of imidazolines with quaternary stereocenters by organocatalytic reaction of N-(heteroarenesulfonyl)imines with isocyanoacetates. ; _journal_issue 12 _journal_name_full 'Organic letters' _journal_page_first 2960 _journal_page_last 2963 _journal_paper_doi 10.1021/ol301256q _journal_volume 14 _journal_year 2012 _chemical_absolute_configuration ad _chemical_formula_moiety 'C30 H26 Br N3 O4 S' _chemical_formula_sum 'C30 H26 Br N3 O4 S' _chemical_formula_weight 604.52 _space_group_IT_number 4 _symmetry_cell_setting monoclinic _symmetry_Int_Tables_number 4 _symmetry_space_group_name_Hall 'P 2yb' _symmetry_space_group_name_H-M 'P 1 21 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _cell_angle_alpha 90.0000 _cell_angle_beta 103.6985(13) _cell_angle_gamma 90.0000 _cell_formula_units_Z 2 _cell_length_a 8.2684(9) _cell_length_b 15.0353(15) _cell_length_c 11.4331(12) _cell_measurement_reflns_used 4895 _cell_measurement_temperature 173 _cell_measurement_theta_max 30.95 _cell_measurement_theta_min 2.54 _cell_volume 1380.9(3) _computing_cell_refinement CrystalClear _computing_data_collection 'CrystalClear (Rigaku/MSC Inc., 2006)' _computing_data_reduction CrystalClear _computing_molecular_graphics 'CrystalStructure 4.0' _computing_publication_material 'CrystalStructure 4.0 (Rigaku, 2010)' _computing_structure_refinement 'CRYSTALS (Carruthers, et al., 1999)' _computing_structure_solution 'SIR2004 (Burla, et al., 2005)' _diffrn_ambient_temperature 173 _diffrn_detector_area_resol_mean 7.314 _diffrn_measured_fraction_theta_full 0.984 _diffrn_measured_fraction_theta_max 0.984 _diffrn_measurement_device_type 'Rigaku Mercury70' _diffrn_measurement_method \w _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71070 _diffrn_reflns_av_R_equivalents 0.0133 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_number 9274 _diffrn_reflns_theta_full 27.49 _diffrn_reflns_theta_max 27.49 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 1.609 _exptl_absorpt_correction_T_max 0.725 _exptl_absorpt_correction_T_min 0.627 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'REQAB (Rigaku, 1998)' _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.454 _exptl_crystal_density_method 'not measured' _exptl_crystal_description prism _exptl_crystal_F_000 620.00 _exptl_crystal_size_max 0.250 _exptl_crystal_size_mid 0.250 _exptl_crystal_size_min 0.200 _refine_diff_density_max 0.408 _refine_diff_density_min -0.387 _refine_ls_abs_structure_details 'Flack, H. D. (1983), Acta Cryst. A39, 876-881. 1293 Friedel Pairs' _refine_ls_abs_structure_Flack -0.025(6) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 0.951 _refine_ls_hydrogen_treatment constr _refine_ls_number_parameters 379 _refine_ls_number_reflns 4528 _refine_ls_R_factor_gt 0.0257 _refine_ls_shift/su_max 0.033 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w = 1/[1.0000\s(Fo^2^)]/(4Fo^2^)' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref 0.0250 _reflns_number_gt 3852 _reflns_number_total 4528 _reflns_threshold_expression F^2^>2.0\s(F^2^) _cod_data_source_file ol301256q_si_001.cif _cod_data_source_block imidazoline _cod_depositor_comments 'Adding full bibliography for 1507838.cif.' _cod_database_code 1507838 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 +X,+Y,+Z 2 -X,1/2+Y,-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 _atom_site_refinement_flags Br39 Br 0.41620(3) 0.34114(3) -0.21465(3) 0.05065(9) Uani 1.0 2 d . S6 S -0.08320(8) 0.05189(4) -0.02013(6) 0.02704(18) Uani 1.0 2 d . O7 O 0.01327(19) -0.02026(10) -0.04813(14) 0.0343(5) Uani 1.0 2 d . O8 O -0.2521(2) 0.03972(10) -0.01251(15) 0.0342(6) Uani 1.0 2 d . O16 O 0.2671(2) -0.02104(10) 0.35566(14) 0.0353(6) Uani 1.0 2 d . O17 O 0.18989(19) 0.08072(9) 0.47648(14) 0.0267(5) Uani 1.0 2 d . N1 N 0.0162(3) 0.08812(12) 0.11325(17) 0.0213(6) Uani 1.0 2 d . N3 N 0.0415(3) 0.17335(11) 0.28114(18) 0.0226(6) Uani 1.0 2 d . N9 N -0.1550(3) 0.21403(13) -0.09958(19) 0.0326(7) Uani 1.0 2 d . C2 C -0.0565(3) 0.14281(14) 0.1863(3) 0.0247(7) Uani 1.0 2 d . C4 C 0.2088(3) 0.13204(13) 0.2859(2) 0.0195(7) Uani 1.0 2 d . C5 C 0.1993(3) 0.09820(14) 0.1558(2) 0.0207(7) Uani 1.0 2 d . C10 C -0.0775(3) 0.13976(15) -0.1223(2) 0.0255(7) Uani 1.0 2 d . C11 C 0.0020(3) 0.12897(16) -0.2143(3) 0.0330(8) Uani 1.0 2 d . C12 C -0.0001(4) 0.20260(17) -0.2906(3) 0.0400(9) Uani 1.0 2 d . C13 C -0.0768(4) 0.27857(19) -0.2678(3) 0.0429(9) Uani 1.0 2 d . C14 C -0.1503(4) 0.28210(17) -0.1732(3) 0.0422(9) Uani 1.0 2 d . C15 C 0.2233(3) 0.05301(15) 0.3727(2) 0.0230(7) Uani 1.0 2 d . C18 C 0.2150(3) 0.01950(13) 0.5734(2) 0.0215(7) Uani 1.0 2 d . C19 C 0.0799(3) -0.03127(14) 0.5859(2) 0.0236(7) Uani 1.0 2 d . C20 C 0.1065(3) -0.08587(14) 0.6879(3) 0.0269(7) Uani 1.0 2 d . C21 C 0.2583(3) -0.08784(14) 0.7727(3) 0.0261(7) Uani 1.0 2 d . C22 C 0.3871(3) -0.03532(14) 0.7559(2) 0.0257(7) Uani 1.0 2 d . C23 C 0.3689(3) 0.02040(14) 0.6554(2) 0.0259(7) Uani 1.0 2 d . C24 C -0.0835(3) -0.02642(17) 0.4979(3) 0.0385(8) Uani 1.0 2 d . C25 C 0.2842(3) -0.14871(17) 0.88146(19) 0.0343(7) Uani 1.0 2 d . C26 C 0.5091(3) 0.07677(17) 0.6353(3) 0.0399(9) Uani 1.0 2 d . C27 C 0.3533(3) 0.19245(13) 0.3388(2) 0.0206(7) Uani 1.0 2 d . C28 C 0.3313(3) 0.26876(14) 0.4020(3) 0.0281(7) Uani 1.0 2 d . C29 C 0.4680(4) 0.32003(15) 0.4568(2) 0.0346(8) Uani 1.0 2 d . C30 C 0.6259(4) 0.29513(16) 0.4495(3) 0.0353(8) Uani 1.0 2 d . C31 C 0.6482(4) 0.21889(16) 0.3883(3) 0.0361(9) Uani 1.0 2 d . C32 C 0.5132(3) 0.16780(15) 0.3330(3) 0.0274(7) Uani 1.0 2 d . C33 C 0.2675(3) 0.16095(14) 0.0747(2) 0.0211(7) Uani 1.0 2 d . C34 C 0.3748(3) 0.12862(15) 0.0072(3) 0.0270(7) Uani 1.0 2 d . C35 C 0.4238(3) 0.18278(16) -0.0766(3) 0.0320(8) Uani 1.0 2 d . C36 C 0.3643(3) 0.26904(16) -0.0923(2) 0.0275(8) Uani 1.0 2 d . C37 C 0.2653(3) 0.30322(15) -0.0220(2) 0.0305(7) Uani 1.0 2 d . C38 C 0.2178(3) 0.24889(13) 0.0603(2) 0.0245(7) Uani 1.0 2 d . H1 H -0.1697 0.1558 0.1668 0.0302 Uiso 1.0 2 calc R H2 H 0.2535 0.0400 0.1585 0.0256 Uiso 1.0 2 calc R H3 H 0.0544 0.0759 -0.2252 0.0389 Uiso 1.0 2 calc R H4 H 0.0492 0.1992 -0.3556 0.0474 Uiso 1.0 2 calc R H5 H -0.0788 0.3282 -0.3167 0.0500 Uiso 1.0 2 calc R H6 H -0.1998 0.3353 -0.1588 0.0488 Uiso 1.0 2 calc R H7 H 0.0203 -0.1221 0.6992 0.0331 Uiso 1.0 2 calc R H8 H 0.4885 -0.0370 0.8125 0.0298 Uiso 1.0 2 calc R H9 H -0.0700 -0.0435 0.4180 0.0472 Uiso 1.0 2 calc R H10 H -0.1622 -0.0670 0.5224 0.0474 Uiso 1.0 2 calc R H11 H -0.1264 0.0345 0.4948 0.0469 Uiso 1.0 2 calc R H12 H 0.3143 -0.1132 0.9553 0.0417 Uiso 1.0 2 calc R H13 H 0.1808 -0.1812 0.8795 0.0412 Uiso 1.0 2 calc R H14 H 0.3735 -0.1912 0.8798 0.0415 Uiso 1.0 2 calc R H15 H 0.4756 0.1394 0.6302 0.0489 Uiso 1.0 2 calc R H16 H 0.6067 0.0688 0.7024 0.0486 Uiso 1.0 2 calc R H17 H 0.5369 0.0589 0.5600 0.0491 Uiso 1.0 2 calc R H18 H 0.2252 0.2853 0.4078 0.0331 Uiso 1.0 2 calc R H19 H 0.4530 0.3714 0.4983 0.0408 Uiso 1.0 2 calc R H20 H 0.7171 0.3299 0.4858 0.0412 Uiso 1.0 2 calc R H21 H 0.7549 0.2017 0.3845 0.0436 Uiso 1.0 2 calc R H22 H 0.5289 0.1166 0.2914 0.0335 Uiso 1.0 2 calc R H23 H 0.4133 0.0704 0.0181 0.0322 Uiso 1.0 2 calc R H24 H 0.4958 0.1615 -0.1214 0.0385 Uiso 1.0 2 calc R H25 H 0.2311 0.3623 -0.0305 0.0359 Uiso 1.0 2 calc R H26 H 0.1508 0.2720 0.1078 0.0309 Uiso 1.0 2 calc 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_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 Br39 0.04716(18) 0.06774(19) 0.04067(17) 0.00224(17) 0.01759(14) 0.02577(17) S6 0.0295(4) 0.0238(3) 0.0263(4) -0.0017(3) 0.0036(3) -0.0032(3) O7 0.0438(12) 0.0273(9) 0.0300(10) 0.0027(8) 0.0054(9) -0.0063(8) O8 0.0237(10) 0.0360(11) 0.0409(12) -0.0108(8) 0.0035(9) 0.0041(9) O16 0.0571(13) 0.0232(9) 0.0285(10) 0.0096(9) 0.0161(10) -0.0011(8) O17 0.0441(11) 0.0198(8) 0.0199(9) -0.0005(8) 0.0150(9) 0.0028(7) N1 0.0209(12) 0.0245(10) 0.0191(11) -0.0026(8) 0.0062(10) -0.0054(9) N3 0.0254(12) 0.0212(10) 0.0216(12) 0.0018(9) 0.0066(10) 0.0001(9) N9 0.0269(13) 0.0313(12) 0.0401(14) 0.0025(9) 0.0092(12) 0.0030(11) C2 0.0252(15) 0.0197(12) 0.0318(15) 0.0018(10) 0.0120(13) 0.0063(11) C4 0.0199(13) 0.0202(12) 0.0187(13) 0.0024(10) 0.0049(11) 0.0001(10) C5 0.0246(14) 0.0185(12) 0.0208(13) 0.0021(10) 0.0089(11) -0.0032(10) C10 0.0269(15) 0.0259(13) 0.0201(13) -0.0006(11) -0.0014(12) -0.0022(11) C11 0.0346(16) 0.0343(15) 0.0300(16) -0.0004(12) 0.0075(14) -0.0097(12) C12 0.058(2) 0.0421(16) 0.0186(14) -0.0039(15) 0.0070(14) 0.0037(13) C13 0.0464(19) 0.0451(17) 0.0323(17) -0.0066(14) -0.0004(15) 0.0148(13) C14 0.0302(16) 0.0324(15) 0.059(2) 0.0072(12) 0.0003(15) 0.0052(15) C15 0.0229(13) 0.0220(12) 0.0237(13) -0.0017(10) 0.0046(11) -0.0037(11) C18 0.0308(15) 0.0185(11) 0.0166(13) 0.0007(10) 0.0081(12) 0.0025(10) C19 0.0261(15) 0.0262(13) 0.0190(13) 0.0002(11) 0.0066(12) -0.0023(10) C20 0.0334(16) 0.0227(12) 0.0270(15) -0.0051(11) 0.0121(13) 0.0017(11) C21 0.0359(16) 0.0225(12) 0.0225(14) 0.0029(11) 0.0120(13) -0.0009(11) C22 0.0250(15) 0.0287(13) 0.0226(14) 0.0004(11) 0.0043(12) 0.0007(11) C23 0.0344(16) 0.0217(12) 0.0240(14) -0.0039(11) 0.0114(13) -0.0011(11) C24 0.0326(16) 0.0469(16) 0.0360(16) -0.0031(13) 0.0082(14) 0.0093(14) C25 0.0471(16) 0.0283(13) 0.0283(13) 0.0038(14) 0.0103(12) 0.0108(13) C26 0.0369(17) 0.0500(18) 0.0341(17) -0.0144(13) 0.0110(14) -0.0034(13) C27 0.0239(14) 0.0221(12) 0.0163(12) -0.0021(10) 0.0059(11) 0.0041(10) C28 0.0343(16) 0.0221(13) 0.0279(15) -0.0019(11) 0.0072(13) 0.0001(11) C29 0.0522(18) 0.0259(15) 0.0250(14) -0.0079(12) 0.0077(13) -0.0017(11) C30 0.0430(18) 0.0344(15) 0.0267(15) -0.0144(12) 0.0046(14) -0.0001(12) C31 0.0313(17) 0.0464(17) 0.0316(16) -0.0052(13) 0.0093(14) 0.0090(14) C32 0.0305(15) 0.0292(13) 0.0234(14) -0.0037(12) 0.0083(13) -0.0021(11) C33 0.0176(13) 0.0249(13) 0.0209(14) 0.0006(10) 0.0049(11) -0.0012(11) C34 0.0256(15) 0.0306(14) 0.0262(14) 0.0013(11) 0.0090(13) -0.0011(11) C35 0.0277(16) 0.0496(17) 0.0202(14) 0.0026(12) 0.0084(12) -0.0008(12) C36 0.0226(14) 0.0364(15) 0.0228(15) -0.0036(11) 0.0042(12) 0.0072(11) C37 0.0315(15) 0.0271(13) 0.0314(15) 0.0021(11) 0.0043(13) 0.0027(11) C38 0.0249(14) 0.0277(13) 0.0241(14) 0.0009(11) 0.0124(12) -0.0046(11) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.003 0.002 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; H H 0.000 0.000 ; International Tables for Crystallography (1992, Vol. C, Table 6.1.1.4) ; N N 0.006 0.003 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; S S 0.125 0.123 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; Br Br -0.290 2.459 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; O O 0.011 0.006 ; International Tables for Crystallography (1992, 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 _geom_angle_publ_flag O7 S6 O8 121.45(10) yes O7 S6 N1 106.07(10) yes O7 S6 C10 108.38(12) yes O8 S6 N1 105.44(11) yes O8 S6 C10 108.31(11) yes N1 S6 C10 106.20(11) yes C15 O17 C18 117.74(17) yes S6 N1 C2 123.75(15) yes S6 N1 C5 125.75(17) yes C2 N1 C5 107.00(17) yes C2 N3 C4 105.99(19) yes C10 N9 C14 115.5(3) yes N1 C2 N3 116.2(2) yes N3 C4 C5 105.23(16) yes N3 C4 C15 105.87(19) yes N3 C4 C27 113.56(17) yes C5 C4 C15 110.09(17) yes C5 C4 C27 115.8(2) yes C15 C4 C27 105.86(17) yes N1 C5 C4 99.36(19) yes N1 C5 C33 111.12(17) yes C4 C5 C33 115.95(18) yes S6 C10 N9 113.8(2) yes S6 C10 C11 120.56(19) yes N9 C10 C11 125.6(3) yes C10 C11 C12 116.3(3) yes C11 C12 C13 118.6(3) yes C12 C13 C14 120.1(3) yes N9 C14 C13 123.9(3) yes O16 C15 O17 124.2(3) yes O16 C15 C4 126.4(3) yes O17 C15 C4 109.23(19) yes O17 C18 C19 117.70(18) yes O17 C18 C23 117.5(2) yes C19 C18 C23 124.5(2) yes C18 C19 C20 115.86(19) yes C18 C19 C24 122.0(2) yes C20 C19 C24 122.2(3) yes C19 C20 C21 122.0(3) yes C20 C21 C22 119.4(3) yes C20 C21 C25 120.8(3) yes C22 C21 C25 119.8(2) yes C21 C22 C23 121.4(2) yes C18 C23 C22 116.8(3) yes C18 C23 C26 121.3(2) yes C22 C23 C26 121.8(2) yes C4 C27 C28 121.1(3) yes C4 C27 C32 119.5(2) yes C28 C27 C32 119.2(2) yes C27 C28 C29 120.0(3) yes C28 C29 C30 120.1(3) yes C29 C30 C31 119.9(3) yes C30 C31 C32 120.4(3) yes C27 C32 C31 120.3(3) yes C5 C33 C34 119.8(2) yes C5 C33 C38 121.5(3) yes C34 C33 C38 118.5(3) yes C33 C34 C35 120.3(3) yes C34 C35 C36 119.1(3) yes Br39 C36 C35 119.7(2) yes Br39 C36 C37 119.15(18) yes C35 C36 C37 121.1(3) yes C36 C37 C38 119.0(3) yes C33 C38 C37 121.7(3) yes loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag Br39 C36 1.898(3) yes S6 O7 1.4270(18) yes S6 O8 1.4313(19) yes S6 N1 1.6443(19) yes S6 C10 1.772(3) yes O16 C15 1.201(3) yes O17 C15 1.347(3) yes O17 C18 1.418(3) yes N1 C2 1.405(4) yes N1 C5 1.485(3) yes N3 C2 1.275(3) yes N3 C4 1.506(3) yes N9 C10 1.343(4) yes N9 C14 1.331(4) yes C4 C5 1.557(4) yes C4 C15 1.534(4) yes C4 C27 1.509(3) yes C5 C33 1.521(4) yes C10 C11 1.376(4) yes C11 C12 1.407(4) yes C12 C13 1.362(4) yes C13 C14 1.361(5) yes C18 C19 1.388(4) yes C18 C23 1.390(3) yes C19 C20 1.401(4) yes C19 C24 1.483(3) yes C20 C21 1.393(3) yes C21 C22 1.376(4) yes C21 C25 1.518(4) yes C22 C23 1.401(4) yes C23 C26 1.497(4) yes C27 C28 1.390(4) yes C27 C32 1.389(4) yes C28 C29 1.389(4) yes C29 C30 1.380(4) yes C30 C31 1.378(4) yes C31 C32 1.379(4) yes C33 C34 1.394(4) yes C33 C38 1.383(3) yes C34 C35 1.388(4) yes C35 C36 1.384(4) yes C36 C37 1.375(4) yes C37 C38 1.372(4) yes loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 30651940