# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2003 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 _publ_contact_author_name 'Prof Karl Anker Jorgensen' _publ_contact_author_address ; Deperment of Chemistry Aarhus University Center for Catalysis DK-8000 Aarhus C DENMARK ; _publ_contact_author_email KAJ@CHEM.AU.DK _publ_section_title ; Formation of optically active chromanes by catalytic asymmetric tandem oxa-Michael addition-Friedel-Crafts alkylation reaction ; # The loop structure below should contain the names and addresses of all # authors, in the required order of publication. Repeat as necessary. loop_ _publ_author_name _publ_author_address 'H.L.van Lingen' ; Department of Organic Chemistry NSRIM, University of Nijmegen, Toernooiveld 1 6525 ED Nijmegen The Netherlands ; 'Wei Zhuang' ; Danish National Research Foundation: Center for Catalysis Department of Chemistry Aarhus University Langelandsgade 140 DK-8000 \%Arhus C Denmark ; 'Tore Hansen' ; Danish National Research Foundation: Center for Catalysis Department of Chemistry Aarhus University Langelandsgade 140 DK-8000 \%Arhus C Denmark ; 'Floris P. J. Rutjes' ; Department of Organic Chemistry NSRIM, University of Nijmegen, Toernooiveld 1 6525 ED Nijmegen The Netherlands ; 'Karl Anker Jorgensen' ; Danish National Research Foundation: Center for Catalysis Department of Chemistry Aarhus University Langelandsgade 140 DK-8000 \%Arhus C Denmark ; #============================================================================== # 4. TEXT _publ_section_abstract ; ; _publ_section_comment ; ; _publ_section_exptl_prep ; ? ; _publ_section_exptl_refinement ; ? ; _publ_section_references ; Altomare,A., Cascarano,G., Giacovazzo,C., Guagliardi,A., Moliterni,.A,G,G., Burla,M.C., Polidori,G., Camalli,M. & Spagna,R. (1997). SIR97. University of Bari, Italy. Becker,P.J. & Coppens, P. (1974). Acta Cryst. A30, 129-153. Burnett,M.N. & Johnson,C.K. (1996). ORTEP-III. Report ORNL-6895. Oak Ridge National Laboratory, Tennessee, USA. Busing,W.R., Martin,K.O. & Levy,H.A. (1962). ORFLS. Report ORNL-TM-305. Oak Ridge National Laboratory, Tennessee, USA. Hazell,A. (1995). KRYSTAL, An integrated system of crystallographic programs. Aarhus University, Denmark. Rogers,D. (1981). Acta Cryst. A37, 734-741. Siemens (1995) SMART, SAINT and XPREP Area-Detector Control and Integration Software. Siemens Analytical X-ray Instruments Inc. Madison, Wisconsin, USA. ; #============================================================================== # If more than one structure is reported, sections 5-10 should be filled in # per structure. For each data set, replace the '?' in the data_? line below # by a unique identifier. #============================================================================== data_CuCl2Npbox _database_code_CSD 206608 #=================================== # 5. CHEMICAL DATA _chemical_name_systematic ; 2,2'-Isopropylidenebis(4-(1-naphthyl)-2-oxazoline) -copper-dichloride ; _chemical_name_common CuCl2(1-Np-box) _chemical_formula_sum 'C29 H26 Cl2 Cu N2 O2' _chemical_formula_moiety 'C29 H26 Cl2 Cu N2 O2' _chemical_formula_weight 569.00 #=================================== # 6. CRYSTAL DATA _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' _symmetry_space_group_name_Hall 'P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz +x,+y,+z 1/2-x,-y,1/2+z -x,1/2+y,1/2-z 1/2+x,1/2-y,-z _cell_length_a 10.066(1) _cell_length_b 12.920(2) _cell_length_c 19.424(2) _cell_angle_alpha 90.000 _cell_angle_beta 90.000 _cell_angle_gamma 90.000 _cell_volume 2526(1) _cell_formula_units_Z 4 _cell_measurement_temperature 120 _cell_measurement_reflns_used 9543 _cell_measurement_theta_min 2.6 _cell_measurement_theta_max 30.5 _exptl_crystal_description box _exptl_crystal_colour green _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.34 _exptl_crystal_size_min 0.24 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.496 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1172 _exptl_absorpt_coefficient_mu 1.106 _exptl_absorpt_correction_type integration _exptl_absorpt_process_details 'XPREP, 1995' _exptl_absorpt_correction_T_min 0.62 _exptl_absorpt_correction_T_max 0.80 #=================================== # 7. EXPERIMENTAL DATA _diffrn_ambient_temperature 120 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'x-ray tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Siemens SMART CCD diffractometer' _diffrn_measurement_method '\w rotation scans with narrow frames' _diffrn_standards_decay_% 0 _diffrn_reflns_number 30861 _diffrn_reflns_av_R_equivalents 0.087 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 2.6 _diffrn_reflns_theta_max 30.5 _diffrn_reflns_reduction_process 30861 _reflns_number_total 7316 _diffrn_measured_fraction_theta_max 0.94 _diffrn_measured_fraction_theta_full 0.998 _diffrn_reflns_theta_full 28.3 _reflns_number_gt 6592 _reflns_threshold_expression I>3\s(I) _computing_data_collection 'SMART (Siemens, 1995)' _computing_cell_refinement 'SAINT (Siemens, 1995)' _computing_data_reduction 'SAINT (Siemens, 1995)' _computing_structure_solution ; SIR97 (Altomare et al., 1997 ), KRYSTAL ; _computing_structure_refinement 'modified ORFLS(1962), KRYSTAL' _computing_molecular_graphics ; ORTEP-III (Burnett & Johnson, 1996), KRYSTAL ; _computing_publication_material KRYSTAL _atom_type_scat_source IntTabIV #=================================== # 8. REFINEMENT DATA _refine_special_details ; ; _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; w= 1/{[\s~cs~(F^2^)+1.03F^2^]^1/2^- |F|}^2^ ; _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_abs_structure_details ;The least squares refinement included a factor according to Rogers (1981) refined against all 6592 significant reflections including 2785 Bijvoet pairs. ; _refine_ls_abs_structure_Rogers 0.97(5) _refine_ls_number_reflns 6592 _refine_ls_number_parameters 430 _refine_ls_number_restraints 0 _refine_ls_number_constraints 0 _refine_ls_R_factor_gt 0.028 _refine_ls_wR_factor_ref 0.035 _refine_ls_goodness_of_fit_ref 1.21 _refine_ls_shift/su_max 0.0003 _refine_ls_shift/su_mean 0.00003 _refine_diff_density_max 0.57(9) _refine_diff_density_min -0.76(9) #========================================== # 9. ATOMIC COORDINATES AND THERMAL PARAMETERS loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_thermal_displace_type Cu -0.00672(2) -0.02177(2) -0.105738(10) 0.01618(9) Uij Cl1 -0.09045(5) 0.13650(3) -0.09881(3) 0.0242(2) Uij Cl2 -0.19345(5) -0.11194(4) -0.11981(3) 0.0276(2) Uij O1 0.3625(1) 0.0054(1) -0.01091(7) 0.0217(7) Uij O2 0.2732(1) -0.2178(1) -0.19487(7) 0.0228(7) Uij N1 0.1519(2) 0.0071(1) -0.04717(7) 0.0173(7) Uij N2 0.1047(2) -0.1178(1) -0.16034(7) 0.0182(7) Uij C1 0.0369(2) -0.0288(2) 0.08509(9) 0.0229(9) Uij C2 -0.0367(2) -0.0485(2) 0.14566(10) 0.0269(10) Uij C3 -0.0716(2) 0.0309(2) 0.18852(9) 0.0247(9) Uij C4 -0.0341(2) 0.1335(1) 0.17252(9) 0.0210(9) Uij C5 -0.0734(2) 0.2182(2) 0.21522(10) 0.0266(10) Uij C6 -0.0380(2) 0.3175(2) 0.19897(11) 0.0287(10) Uij C7 0.0403(2) 0.3373(2) 0.14053(11) 0.0281(10) Uij C8 0.0782(2) 0.2581(1) 0.09795(10) 0.0219(9) Uij C9 0.0408(2) 0.1540(1) 0.11186(9) 0.0180(8) Uij C10 0.0752(2) 0.0697(1) 0.06787(9) 0.0178(8) Uij C11 0.1580(2) 0.0927(1) 0.00413(9) 0.0179(8) Uij C12 0.3078(2) 0.0998(2) 0.01981(11) 0.0226(9) Uij C13 0.2662(2) -0.0355(1) -0.04946(8) 0.0168(8) Uij C14 0.3070(2) -0.1338(1) -0.08654(9) 0.0181(8) Uij C15 0.2890(3) -0.2238(2) -0.03479(11) 0.0289(11) Uij C16 0.4529(2) -0.1275(2) -0.10969(12) 0.0295(10) Uij C17 0.2206(2) -0.1539(1) -0.14793(9) 0.0178(8) Uij C18 0.1725(2) -0.2324(2) -0.24869(10) 0.0239(10) Uij C19 0.0641(2) -0.1524(1) -0.23040(9) 0.0196(9) Uij C20 0.0564(2) -0.0595(1) -0.27807(9) 0.0196(8) Uij C21 -0.0325(2) -0.0620(2) -0.33556(9) 0.0211(9) Uij C22 -0.1095(2) -0.1494(2) -0.35295(10) 0.0254(10) Uij C23 -0.1910(2) -0.1483(2) -0.40943(11) 0.0347(12) Uij C24 -0.2000(2) -0.0597(2) -0.45178(11) 0.0403(14) Uij C25 -0.1271(2) 0.0254(2) -0.43628(11) 0.0359(12) Uij C26 -0.0411(2) 0.0282(2) -0.37864(10) 0.0275(9) Uij C27 0.0411(2) 0.1145(2) -0.36426(11) 0.0331(11) Uij C28 0.1287(3) 0.1134(2) -0.31128(12) 0.0324(11) Uij C29 0.1356(2) 0.0258(2) -0.26752(10) 0.0267(10) Uij H1 0.058(3) -0.084(2) 0.0563(14) 0.036(7) Uiso H2 -0.055(3) -0.118(2) 0.1547(12) 0.030(6) Uiso H3 -0.114(3) 0.027(2) 0.2275(13) 0.035(7) Uiso H5 -0.130(2) 0.199(2) 0.2558(12) 0.022(6) Uiso H6 -0.066(2) 0.373(2) 0.2261(12) 0.029(6) Uiso H7 0.074(3) 0.408(2) 0.1289(14) 0.043(8) Uiso H8 0.125(3) 0.273(2) 0.0607(12) 0.023(6) Uiso H11 0.120(2) 0.152(2) -0.0154(10) 0.011(5) Uiso H12a 0.324(2) 0.098(2) 0.0651(12) 0.016(5) Uiso H12b 0.352(3) 0.159(2) -0.0040(12) 0.027(6) Uiso H15a 0.317(2) -0.296(2) -0.0546(12) 0.025(6) Uiso H15b 0.346(3) -0.209(2) 0.0071(14) 0.043(8) Uiso H15c 0.197(3) -0.229(2) -0.0151(12) 0.028(6) Uiso H16a 0.488(3) -0.194(2) -0.1263(12) 0.035(7) Uiso H16b 0.465(3) -0.075(2) -0.1462(14) 0.045(8) Uiso H16c 0.506(3) -0.114(2) -0.0690(12) 0.029(6) Uiso H18a 0.218(3) -0.218(2) -0.2933(13) 0.029(7) Uiso H18b 0.139(3) -0.311(2) -0.2457(14) 0.039(7) Uiso H19 -0.025(2) -0.185(2) -0.2259(10) 0.009(5) Uiso H22 -0.103(2) -0.207(2) -0.3284(12) 0.019(6) Uiso H23 -0.242(3) -0.215(2) -0.4148(13) 0.036(7) Uiso H24 -0.255(3) -0.063(2) -0.4871(15) 0.048(8) Uiso H25 -0.135(3) 0.092(2) -0.4650(14) 0.037(7) Uiso H27 0.030(3) 0.176(2) -0.3896(13) 0.042(7) Uiso H28 0.192(3) 0.171(2) -0.3024(13) 0.034(7) Uiso H29 0.198(3) 0.035(2) -0.2318(14) 0.045(8) Uiso 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 Cu 0.01334(10) 0.02016(10) 0.01504(9) 0.00203(8) -0.00064(8) -0.00070(7) Cl1 0.0214(2) 0.0225(2) 0.0287(2) 0.0059(2) -0.0021(2) 0.0032(2) Cl2 0.0172(2) 0.0311(2) 0.0346(3) -0.0035(2) 0.0013(2) -0.0055(2) O1 0.0177(6) 0.0223(7) 0.0249(6) 0.0028(5) -0.0049(5) -0.0069(5) O2 0.0231(7) 0.0254(7) 0.0199(6) 0.0067(6) -0.0011(5) -0.0079(5) N1 0.0183(7) 0.0179(7) 0.0158(6) 0.0026(6) -0.0018(6) -0.0038(5) N2 0.0180(8) 0.0233(7) 0.0133(6) 0.0005(6) -0.0011(6) -0.0014(5) C1 0.0317(10) 0.0174(8) 0.0195(8) 0.0013(8) -0.0021(7) -0.0024(7) C2 0.0387(13) 0.0204(9) 0.0217(8) -0.0034(8) -0.0016(8) 0.0041(7) C3 0.0296(10) 0.0301(10) 0.0144(8) 0.0010(9) -0.0011(7) 0.0021(7) C4 0.0230(9) 0.0244(9) 0.0156(7) 0.0040(7) -0.0040(7) -0.0024(7) C5 0.0280(11) 0.0346(11) 0.0171(8) 0.0070(9) -0.0034(8) -0.0077(8) C6 0.0300(11) 0.0282(10) 0.0281(9) 0.0080(8) -0.0055(8) -0.0121(8) C7 0.0332(11) 0.0184(9) 0.0328(10) 0.0024(8) -0.0050(9) -0.0050(8) C8 0.0229(9) 0.0197(8) 0.0231(9) 0.0005(7) -0.0009(8) -0.0033(7) C9 0.0182(8) 0.0187(8) 0.0171(7) 0.0018(6) -0.0040(7) -0.0019(6) C10 0.0190(9) 0.0181(8) 0.0162(7) 0.0017(7) -0.0027(7) -0.0009(6) C11 0.0202(9) 0.0160(8) 0.0175(8) 0.0021(7) -0.0027(7) -0.0026(6) C12 0.0206(9) 0.0210(9) 0.0263(10) 0.0016(7) -0.0036(8) -0.0075(7) C13 0.0175(8) 0.0194(8) 0.0135(7) 0.0014(7) -0.0024(6) 0.0002(6) C14 0.0161(8) 0.0197(8) 0.0186(8) 0.0039(7) -0.0013(6) -0.0024(6) C15 0.0429(14) 0.0208(10) 0.0230(9) 0.0035(9) -0.0054(9) 0.0011(7) C16 0.0159(8) 0.0343(11) 0.0383(11) 0.0017(8) -0.0001(9) -0.0146(10) C17 0.0190(9) 0.0180(8) 0.0162(7) 0.0006(7) 0.0019(6) -0.0016(6) C18 0.0273(11) 0.0256(10) 0.0188(9) 0.0030(8) -0.0040(7) -0.0048(7) C19 0.0223(9) 0.0222(9) 0.0143(7) 0.0000(7) -0.0020(7) -0.0019(6) C20 0.0212(9) 0.0220(9) 0.0155(8) 0.0018(7) 0.0015(7) -0.0027(6) C21 0.0202(9) 0.0276(9) 0.0154(7) 0.0073(7) 0.0023(7) -0.0029(6) C22 0.0229(10) 0.0324(10) 0.0208(9) 0.0050(8) -0.0003(8) -0.0086(8) C23 0.0259(11) 0.0528(14) 0.0253(10) 0.0092(10) -0.0041(9) -0.0163(10) C24 0.0278(11) 0.0754(19) 0.0178(9) 0.0238(12) -0.0044(9) -0.0075(10) C25 0.0334(12) 0.0546(14) 0.0197(9) 0.0245(12) 0.0054(8) 0.0047(10) C26 0.0295(10) 0.0349(10) 0.0179(8) 0.0154(9) 0.0071(7) 0.0022(8) C27 0.0432(13) 0.0278(10) 0.0281(10) 0.0098(9) 0.0143(9) 0.0070(8) C28 0.0407(13) 0.0245(10) 0.0320(11) -0.0022(9) 0.0104(10) 0.0015(8) C29 0.0314(11) 0.0262(9) 0.0224(9) -0.0043(9) 0.0007(8) -0.0018(8) #================================= # 10. MOLECULAR GEOMETRY loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance Cu N2 1.981(2) Cu N1 1.995(2) Cu Cl1 2.216(1) Cu Cl2 2.228(1) O1 C13 1.334(2) O1 C12 1.465(2) O2 C17 1.339(2) O2 C18 1.469(2) N1 C13 1.277(2) N1 C11 1.490(2) N2 C17 1.279(2) N2 C19 1.490(2) C1 C10 1.371(3) C1 C2 1.413(3) C2 C3 1.368(3) C3 C4 1.413(3) C4 C9 1.424(3) C4 C5 1.428(3) C5 C6 1.368(3) C6 C7 1.406(3) C7 C8 1.370(3) C8 C9 1.423(3) C9 C10 1.428(2) C10 C11 1.521(3) C11 C12 1.542(3) C13 C14 1.516(2) C14 C17 1.499(2) C14 C16 1.538(3) C14 C15 1.548(3) C18 C19 1.543(3) C19 C20 1.519(3) C20 C21 1.432(3) C20 C29 1.375(3) C21 C22 1.410(3) C21 C26 1.437(3) C22 C23 1.370(3) C23 C24 1.412(4) C24 C25 1.356(4) C25 C26 1.416(3) C26 C27 1.417(4) C27 C28 1.355(4) C28 C29 1.417(3) C1 H1 0.928(27) C2 H2 0.927(26) C3 H3 0.869(27) C5 H5 1.004(24) C6 H6 0.932(26) C7 H7 0.999(29) C8 H8 0.882(25) C11 H11 0.942(22) C12 H12a 0.895(23) C12 H12b 1.003(26) C15 H15c 1.003(27) C15 H15b 1.011(30) C15 H15a 1.041(25) C16 H16c 0.970(26) C16 H16a 0.979(27) C16 H16b 0.991(29) C18 H18a 0.998(26) C18 H18b 1.074(30) C19 H19 0.989(22) C22 H22 0.891(23) C23 H23 1.014(29) C24 H24 0.883(31) C25 H25 1.024(27) C27 H27 0.943(28) C28 H28 0.992(28) C29 H29 0.946(29) loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle N1 Cu N2 88.23(6) Cl1 Cu N2 145.70(5) Cl2 Cu N2 94.85(5) Cl1 Cu N1 95.59(5) Cl2 Cu N1 147.40(5) Cl1 Cu Cl2 99.74(2) C12 O1 C13 106.6(1) C17 O2 C18 106.9(2) C11 N1 C13 107.8(1) Cu N1 C13 128.4(1) Cu N1 C11 123.6(1) C17 N2 C19 108.2(2) Cu N2 C17 130.1(1) Cu N2 C19 121.4(1) C2 C1 C10 121.2(2) C1 C2 C3 120.4(2) C2 C3 C4 120.1(2) C3 C4 C9 119.9(2) C3 C4 C5 121.1(2) C5 C4 C9 119.0(2) C4 C5 C6 120.8(2) C5 C6 C7 120.2(2) C6 C7 C8 120.5(2) C7 C8 C9 121.2(2) C4 C9 C8 118.2(2) C8 C9 C10 122.9(2) C4 C9 C10 118.8(2) C1 C10 C9 119.6(2) C1 C10 C11 122.3(2) C9 C10 C11 118.1(2) N1 C11 C10 112.1(2) N1 C11 C12 102.5(1) C10 C11 C12 112.7(2) O1 C12 C11 103.7(1) O1 C13 N1 117.7(2) N1 C13 C14 128.4(2) O1 C13 C14 113.7(2) C13 C14 C17 111.5(1) C16 C14 C17 109.3(2) C15 C14 C17 108.6(2) C13 C14 C16 110.7(2) C13 C14 C15 106.8(1) C15 C14 C16 109.9(2) O2 C17 N2 117.2(2) N2 C17 C14 128.0(2) O2 C17 C14 114.8(2) O2 C18 C19 103.8(1) N2 C19 C20 109.5(2) N2 C19 C18 102.5(1) C18 C19 C20 115.1(2) C21 C20 C29 119.8(2) C19 C20 C29 120.9(2) C19 C20 C21 119.3(2) C20 C21 C22 123.3(2) C22 C21 C26 118.4(2) C20 C21 C26 118.3(2) C21 C22 C23 120.8(2) C22 C23 C24 120.9(2) C23 C24 C25 119.6(2) C24 C25 C26 121.8(2) C25 C26 C27 122.2(2) C21 C26 C25 118.5(2) C21 C26 C27 119.2(2) C26 C27 C28 121.4(2) C27 C28 C29 119.8(2) C20 C29 C28 121.5(2) C10 C1 H1 119.8(17) C2 C1 H1 119.0(17) C3 C2 H2 123.9(16) C1 C2 H2 115.6(16) C2 C3 H3 127.7(19) C4 C3 H3 112.1(18) C6 C5 H5 123.9(14) C4 C5 H5 115.2(14) C5 C6 H6 120.8(16) C7 C6 H6 119.0(16) C8 C7 H7 116.9(17) C6 C7 H7 122.5(16) C7 C8 H8 118.2(16) C9 C8 H8 120.6(16) N1 C11 H11 108.7(13) C10 C11 H11 105.4(13) C12 C11 H11 115.5(13) H12a C12 H12b 112.9(20) O1 C12 H12a 108.0(15) C11 C12 H12a 112.1(15) O1 C12 H12b 106.5(14) C11 C12 H12b 113.0(15) H15b C15 H15c 102.9(22) H15a C15 H15c 109.4(20) C14 C15 H15c 113.7(15) H15a C15 H15b 108.1(21) C14 C15 H15b 108.6(17) C14 C15 H15a 113.5(13) H16a C16 H16c 103.4(21) H16b C16 H16c 112.8(22) C14 C16 H16c 107.3(16) H16a C16 H16b 108.8(21) C14 C16 H16a 113.1(17) C14 C16 H16b 111.2(18) H18a C18 H18b 111.4(20) O2 C18 H18a 106.1(16) C19 C18 H18a 113.9(15) O2 C18 H18b 107.6(15) C19 C18 H18b 113.3(16) N2 C19 H19 107.0(12) C20 C19 H19 109.9(12) C18 C19 H19 112.3(12) C23 C22 H22 118.7(16) C21 C22 H22 120.4(16) C22 C23 H23 112.2(16) C24 C23 H23 126.9(16) C25 C24 H24 123.7(21) C23 C24 H24 116.7(21) C24 C25 H25 120.9(16) C26 C25 H25 117.3(16) C28 C27 H27 118.8(17) C26 C27 H27 119.6(17) C27 C28 H28 122.8(16) C29 C28 H28 117.4(16) C20 C29 H29 126.7(19) C28 C29 H29 111.8(19) #=================================== data_CuBr2Npbox _database_code_CSD 206609 #=================================== # 5. CHEMICAL DATA _chemical_name_systematic ; 2,2'-Isopropylidenebis(4-(1-naphthyl)-2-oxazoline) -copper-dibromide ; _chemical_name_common CuBr2(1-Np-box) _chemical_formula_sum 'C29 H26 Br2 Cu N2 O2' _chemical_formula_moiety 'C29 H26 Br2 Cu N2 O2' _chemical_formula_weight 657.91 #=================================== # 6. CRYSTAL DATA _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' _symmetry_space_group_name_Hall 'P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz +x,+y,+z 1/2-x,-y,1/2+z -x,1/2+y,1/2-z 1/2+x,1/2-y,-z _cell_length_a 10.2389(9) _cell_length_b 13.089(1) _cell_length_c 19.466(2) _cell_angle_alpha 90.000 _cell_angle_beta 90.000 _cell_angle_gamma 90.000 _cell_volume 2608.8(4) _cell_formula_units_Z 4 _cell_measurement_temperature 120 _cell_measurement_reflns_used 6910 _cell_measurement_theta_min 2.5 _cell_measurement_theta_max 30.5 _exptl_crystal_description needle _exptl_crystal_colour green _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.675 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1316 _exptl_absorpt_coefficient_mu 3.940 _exptl_absorpt_correction_type integration _exptl_absorpt_process_details 'XPREP, 1995' _exptl_absorpt_correction_T_min 0.44 _exptl_absorpt_correction_T_max 0.87 #=================================== # 7. EXPERIMENTAL DATA _diffrn_ambient_temperature 120 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'x-ray tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Siemens SMART CCD diffractometer' _diffrn_measurement_method '\w rotation scans with narrow frames' _diffrn_standards_decay_% 0 _diffrn_reflns_number 24177 _diffrn_reflns_av_R_equivalents 0.079 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 2.5 _diffrn_reflns_theta_max 30.5 _diffrn_reflns_reduction_process 24177 _reflns_number_total 7639 _diffrn_measured_fraction_theta_max 0.97 _diffrn_measured_fraction_theta_full 1.00 _diffrn_reflns_theta_full 28.3 _reflns_number_gt 5147 _reflns_threshold_expression I>3\s(I) _computing_data_collection 'SMART (Siemens, 1995)' _computing_cell_refinement 'SAINT (Siemens, 1995)' _computing_data_reduction 'SAINT (Siemens, 1995)' _computing_structure_solution ; SIR97 (Altomare et al., 1997 ), KRYSTAL ; _computing_structure_refinement 'modified ORFLS(1962), KRYSTAL' _computing_molecular_graphics ; ORTEP-III (Burnett & Johnson, 1996), KRYSTAL ; _computing_publication_material KRYSTAL _atom_type_scat_source IntTabIV #=================================== # 8. REFINEMENT DATA _refine_special_details ; ; _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; w= 1/{[\s~cs~(F^2^)+1.03F^2^]^1/2^- |F|}^2^ ; _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_abs_structure_details ;The least squares refinement included a factor according to Rogers (1981) refined against all 6592 significant reflections including 2027 Bijvoet pairs. ; _refine_ls_abs_structure_Rogers 1.04(2) _refine_ls_number_reflns 5147 _refine_ls_number_parameters 430 _refine_ls_number_restraints 0 _refine_ls_number_constraints 0 _refine_ls_R_factor_gt 0.033 _refine_ls_wR_factor_ref 0.035 _refine_ls_goodness_of_fit_ref 0.90 _refine_ls_shift/su_max 0.0024 _refine_ls_shift/su_mean 0.0003 _refine_diff_density_max 1.3(2) _refine_diff_density_min -1.4(2) #========================================== # 9. ATOMIC COORDINATES AND THERMAL PARAMETERS loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_thermal_displace_type Br1 -0.08824(4) 0.14432(3) -0.09683(2) 0.0214(2) Uij Br2 -0.19641(4) -0.11227(4) -0.11902(2) 0.0231(2) Uij Cu 0.00114(4) -0.02085(4) -0.10429(3) 0.0142(2) Uij O1 0.3639(3) 0.0029(2) -0.0089(2) 0.020(2) Uij O2 0.2753(3) -0.2137(2) -0.1944(2) 0.022(2) Uij N1 0.1574(3) 0.0074(3) -0.0458(2) 0.015(2) Uij N2 0.1091(3) -0.1161(3) -0.1594(2) 0.015(2) Uij C1 0.0455(5) -0.0284(4) 0.0868(2) 0.024(2) Uij C2 -0.0270(5) -0.0482(4) 0.1460(3) 0.028(3) Uij C3 -0.0647(5) 0.0288(4) 0.1883(3) 0.026(3) Uij C4 -0.0316(4) 0.1316(4) 0.1723(2) 0.021(2) Uij C5 -0.0728(5) 0.2152(4) 0.2135(2) 0.027(3) Uij C6 -0.0411(5) 0.3131(4) 0.1971(3) 0.030(3) Uij C7 0.0355(5) 0.3338(4) 0.1385(2) 0.025(3) Uij C8 0.0754(4) 0.2554(3) 0.0972(3) 0.020(2) Uij C9 0.0430(4) 0.1524(3) 0.1113(2) 0.016(2) Uij C10 0.0803(4) 0.0689(3) 0.0690(2) 0.016(2) Uij C11 0.1646(4) 0.0912(3) 0.0059(2) 0.016(2) Uij C12 0.3123(4) 0.0950(4) 0.0227(3) 0.023(2) Uij C13 0.2691(4) -0.0365(3) -0.0481(2) 0.015(2) Uij C14 0.3088(4) -0.1318(3) -0.0862(2) 0.015(2) Uij C15 0.2925(6) -0.2220(4) -0.0350(3) 0.028(3) Uij C16 0.4522(4) -0.1251(4) -0.1096(3) 0.030(3) Uij C17 0.2232(4) -0.1520(3) -0.1474(2) 0.016(2) Uij C18 0.1766(5) -0.2268(4) -0.2489(2) 0.023(3) Uij C19 0.0691(4) -0.1500(3) -0.2295(2) 0.017(2) Uij C20 0.0589(4) -0.0573(3) -0.2762(2) 0.017(2) Uij C21 -0.0314(4) -0.0576(3) -0.3326(2) 0.017(2) Uij C22 -0.1098(4) -0.1433(4) -0.3500(2) 0.020(2) Uij C23 -0.1903(4) -0.1414(4) -0.4060(2) 0.029(2) Uij C24 -0.1988(5) -0.0548(4) -0.4480(2) 0.031(3) Uij C25 -0.1263(5) 0.0295(5) -0.4322(3) 0.030(3) Uij C26 -0.0404(4) 0.0311(4) -0.3751(2) 0.022(2) Uij C27 0.0414(4) 0.1165(4) -0.3613(2) 0.025(2) Uij C28 0.1284(5) 0.1131(4) -0.3087(3) 0.029(3) Uij C29 0.1361(4) 0.0265(4) -0.2663(2) 0.024(2) Uij H1 0.080(5) -0.089(4) 0.056(2) 0.032(14) Uiso H2 -0.040(4) -0.107(3) 0.159(2) 0.006(11) Uiso H3 -0.106(5) 0.015(4) 0.229(3) 0.035(15) Uiso H5 -0.127(5) 0.200(4) 0.249(3) 0.042(17) Uiso H6 -0.075(4) 0.371(3) 0.226(2) 0.016(11) Uiso H7 0.066(4) 0.396(3) 0.126(2) 0.014(11) Uiso H8 0.117(5) 0.269(4) 0.056(2) 0.024(13) Uiso H11 0.133(4) 0.151(3) -0.017(2) 0.007(10) Uiso H12a 0.327(4) 0.092(3) 0.072(2) 0.012(11) Uiso H12b 0.355(5) 0.154(4) 0.000(3) 0.038(15) Uiso H15a 0.321(4) -0.289(3) -0.055(2) 0.001(9) Uiso H15b 0.350(6) -0.210(4) 0.010(3) 0.058(19) Uiso H15c 0.198(5) -0.229(4) -0.016(2) 0.037(14) Uiso H16a 0.483(5) -0.184(4) -0.129(2) 0.023(13) Uiso H16b 0.460(5) -0.065(4) -0.146(3) 0.040(16) Uiso H16c 0.510(5) -0.103(4) -0.073(3) 0.035(14) Uiso H18a 0.226(4) -0.210(4) -0.293(2) 0.024(13) Uiso H18b 0.148(6) -0.288(5) -0.248(3) 0.051(19) Uiso H19 -0.009(4) -0.185(3) -0.224(2) 0.002(10) Uiso H22 -0.108(4) -0.206(3) -0.325(2) 0.003(10) Uiso H23 -0.238(5) -0.220(5) -0.412(3) 0.056(18) Uiso H24 -0.251(5) -0.054(4) -0.484(3) 0.035(16) Uiso H25 -0.131(5) 0.084(4) -0.457(2) 0.026(14) Uiso H27 0.035(4) 0.180(3) -0.389(2) 0.011(10) Uiso H28 0.191(4) 0.173(3) -0.301(2) 0.006(10) Uiso H29 0.198(5) 0.027(4) -0.227(3) 0.044(16) Uiso 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 Br1 0.0179(2) 0.0219(2) 0.0244(2) 0.0055(2) -0.0019(2) 0.0030(2) Br2 0.0119(2) 0.0292(2) 0.0281(3) -0.0028(2) 0.0008(2) -0.0043(2) Cu 0.0097(2) 0.0205(2) 0.0124(2) 0.0022(2) -0.0011(2) -0.0011(2) O1 0.015(1) 0.024(2) 0.022(2) 0.004(1) -0.005(1) -0.009(1) O2 0.018(2) 0.032(2) 0.015(2) 0.006(1) -0.003(1) -0.009(1) N1 0.015(2) 0.019(2) 0.012(2) 0.001(1) -0.001(1) -0.004(1) N2 0.013(2) 0.022(2) 0.011(2) -0.001(1) 0.000(1) -0.002(1) C1 0.034(3) 0.021(2) 0.016(2) 0.005(2) -0.004(2) -0.004(2) C2 0.038(3) 0.026(3) 0.020(3) -0.004(2) -0.004(2) 0.006(2) C3 0.027(3) 0.035(3) 0.016(2) -0.003(2) -0.001(2) 0.005(2) C4 0.015(2) 0.033(3) 0.015(2) 0.002(2) -0.004(2) -0.001(2) C5 0.023(3) 0.041(3) 0.016(3) 0.007(2) -0.002(2) -0.007(2) C6 0.031(3) 0.031(3) 0.028(3) 0.006(2) -0.005(2) -0.013(2) C7 0.028(3) 0.022(3) 0.026(3) 0.005(2) -0.001(2) -0.004(2) C8 0.017(2) 0.024(2) 0.020(2) 0.002(2) -0.003(2) -0.006(2) C9 0.013(2) 0.021(2) 0.014(2) 0.002(2) -0.005(2) -0.003(2) C10 0.017(2) 0.019(2) 0.011(2) 0.002(2) -0.005(2) 0.002(2) C11 0.016(2) 0.019(2) 0.013(2) 0.005(2) -0.004(2) -0.007(2) C12 0.015(2) 0.025(3) 0.028(3) 0.001(2) -0.006(2) -0.012(2) C13 0.017(2) 0.017(2) 0.011(2) -0.002(2) -0.002(2) 0.000(2) C14 0.010(2) 0.017(2) 0.018(2) 0.001(2) -0.003(2) -0.004(2) C15 0.038(3) 0.023(3) 0.023(3) 0.001(2) -0.006(2) -0.001(2) C16 0.012(2) 0.041(3) 0.036(3) 0.002(2) 0.001(2) -0.017(3) C17 0.014(2) 0.020(2) 0.014(2) 0.000(2) 0.001(2) -0.003(2) C18 0.026(2) 0.025(3) 0.017(2) 0.001(2) -0.006(2) -0.008(2) C19 0.016(2) 0.024(2) 0.010(2) -0.004(2) -0.001(2) 0.000(2) C20 0.015(2) 0.027(2) 0.009(2) 0.003(2) 0.002(2) -0.003(2) C21 0.014(2) 0.023(2) 0.014(2) 0.005(2) 0.004(2) -0.004(2) C22 0.013(2) 0.031(2) 0.017(2) 0.007(2) -0.001(2) -0.004(2) C23 0.018(2) 0.045(3) 0.023(2) 0.004(2) -0.003(2) -0.010(2) C24 0.025(3) 0.055(4) 0.014(2) 0.017(3) -0.002(2) -0.003(2) C25 0.029(3) 0.043(3) 0.020(3) 0.017(2) 0.008(2) 0.013(2) C26 0.021(2) 0.032(2) 0.012(2) 0.010(2) 0.006(2) -0.001(2) C27 0.027(2) 0.030(3) 0.019(2) 0.004(2) 0.010(2) 0.004(2) C28 0.032(3) 0.025(2) 0.029(3) -0.005(2) 0.007(2) -0.001(2) C29 0.025(2) 0.028(3) 0.018(3) -0.004(2) 0.000(2) 0.000(2) #================================= # 10. MOLECULAR GEOMETRY loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance Cu Br1 2.352(1) Cu Br2 2.368(1) Cu N1 1.998(3) Cu N2 1.982(3) O1 C13 1.339(5) O1 C12 1.453(5) O2 C17 1.332(5) O2 C18 1.475(5) N1 C13 1.280(5) N1 C11 1.491(5) N2 C17 1.281(5) N2 C19 1.493(5) C1 C10 1.367(6) C1 C2 1.394(7) C2 C3 1.357(7) C3 C4 1.423(7) C4 C5 1.421(7) C4 C9 1.436(6) C5 C6 1.361(7) C6 C7 1.410(7) C7 C8 1.366(6) C8 C9 1.415(6) C9 C10 1.422(6) C10 C11 1.529(6) C11 C12 1.548(6) C13 C14 1.507(5) C14 C17 1.502(5) C14 C16 1.539(6) C14 C15 1.555(6) C18 C19 1.538(6) C19 C20 1.520(6) C20 C29 1.367(6) C20 C21 1.434(6) C21 C22 1.421(6) C21 C26 1.429(6) C22 C23 1.367(6) C23 C24 1.400(7) C24 C25 1.365(8) C25 C26 1.418(7) C26 C27 1.422(7) C27 C28 1.359(7) C28 C29 1.403(7) C1 H1 1.06(5) C2 H2 0.82(4) C3 H3 0.91(5) C5 H5 0.91(6) C6 H6 1.01(4) C7 H7 0.91(4) C8 H8 0.93(5) C11 H11 0.96(4) C12 H12a 0.98(4) C12 H12b 0.99(5) C15 H15a 1.00(4) C15 H15c 1.04(5) C15 H15b 1.07(6) C16 H16a 0.92(5) C16 H16c 0.98(5) C16 H16b 1.06(5) C18 H18b 0.85(6) C18 H18a 1.03(5) C19 H19 0.93(4) C22 H22 0.95(4) C23 H23 1.15(6) C24 H24 0.89(5) C25 H25 0.86(5) C27 H27 0.99(4) C28 H28 1.02(4) C29 H29 0.99(5) loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle N1 Cu N2 88.7(1) Br1 Cu N2 146.0(1) Br2 Cu N2 95.3(1) Br1 Cu N1 96.1(1) Br2 Cu N1 147.9(1) Br1 Cu Br2 98.03(2) C12 O1 C13 107.3(3) C17 O2 C18 106.9(3) C11 N1 C13 108.0(3) Cu N1 C13 127.8(3) Cu N1 C11 124.1(3) C17 N2 C19 108.0(3) Cu N2 C17 129.9(3) Cu N2 C19 121.9(3) C2 C1 C10 121.5(5) C1 C2 C3 120.9(5) C2 C3 C4 120.1(5) C3 C4 C5 122.2(4) C5 C4 C9 118.6(4) C3 C4 C9 119.1(4) C4 C5 C6 121.4(5) C5 C6 C7 120.2(5) C6 C7 C8 119.9(5) C7 C8 C9 122.1(5) C8 C9 C10 123.8(4) C4 C9 C8 117.8(4) C4 C9 C10 118.4(4) C1 C10 C9 119.9(4) C1 C10 C11 122.0(4) C9 C10 C11 118.1(4) N1 C11 C10 112.0(4) N1 C11 C12 102.4(3) C10 C11 C12 112.9(4) O1 C12 C11 103.9(3) O1 C13 N1 117.1(4) N1 C13 C14 129.0(4) O1 C13 C14 113.8(3) C13 C14 C17 112.2(3) C16 C14 C17 109.4(3) C15 C14 C17 108.2(3) C13 C14 C16 110.9(4) C13 C14 C15 106.5(3) C15 C14 C16 109.6(4) O2 C17 N2 117.5(4) N2 C17 C14 127.8(4) O2 C17 C14 114.7(3) O2 C18 C19 103.8(3) N2 C19 C20 109.1(4) N2 C19 C18 102.8(3) C18 C19 C20 115.1(4) C21 C20 C29 118.9(4) C19 C20 C29 121.1(4) C19 C20 C21 120.0(4) C22 C21 C26 117.8(4) C20 C21 C22 123.3(4) C20 C21 C26 118.9(4) C21 C22 C23 121.1(5) C22 C23 C24 121.2(5) C23 C24 C25 119.3(5) C24 C25 C26 121.7(5) C25 C26 C27 121.7(5) C21 C26 C25 118.8(5) C21 C26 C27 119.4(4) C26 C27 C28 120.1(5) C27 C28 C29 120.5(5) C20 C29 C28 122.2(4) C10 C1 H1 118(3) C2 C1 H1 121(3) C3 C2 H2 118(3) C1 C2 H2 121(3) C2 C3 H3 121(3) C4 C3 H3 119(3) C6 C5 H5 122(4) C4 C5 H5 117(4) C5 C6 H6 120(2) C7 C6 H6 120(3) C8 C7 H7 114(3) C6 C7 H7 126(3) C7 C8 H8 120(3) C9 C8 H8 117(3) N1 C11 H11 106(2) C10 C11 H11 110(2) C12 C11 H11 113(2) H12a C12 H12b 113(4) O1 C12 H12a 109(3) C11 C12 H12a 111(2) O1 C12 H12b 108(3) C11 C12 H12b 111(3) H15a C15 H15c 109(4) H15a C15 H15b 107(4) C14 C15 H15a 112(2) H15b C15 H15c 104(4) C14 C15 H15c 113(3) C14 C15 H15b 111(3) H16a C16 H16c 110(4) H16a C16 H16b 110(4) C14 C16 H16a 114(3) H16b C16 H16c 102(4) C14 C16 H16c 113(3) C14 C16 H16b 108(3) H18a C18 H18b 114(5) O2 C18 H18b 109(4) C19 C18 H18b 111(4) O2 C18 H18a 104(3) C19 C18 H18a 115(3) N2 C19 H19 106(2) C20 C19 H19 114(2) C18 C19 H19 109(2) C23 C22 H22 116(2) C21 C22 H22 123(2) C22 C23 H23 109(3) C24 C23 H23 130(3) C25 C24 H24 120(4) C23 C24 H24 121(4) C24 C25 H25 121(3) C26 C25 H25 117(3) C28 C27 H27 119(2) C26 C27 H27 121(2) C27 C28 H28 120(2) C29 C28 H28 120(2) C20 C29 H29 119(3) C28 C29 H29 119(3)