# 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 loop_ _publ_author_name 'Elena I. Klimova' 'Leon V. Backinowsky' 'Simon Hernandez Ortega' 'Tatiana Klimova' _publ_contact_author_name 'Prof Elena I Klimova' _publ_contact_author_address ; Facultad de Quimica Universidad Nacional Autonoma de Mexico Cd. Universitaria Coyoacan C.P MexicoD.F 04510 MEXICO ; _publ_contact_author_email KLIMOVA@SERVIDOR.UNAM.MX _publ_section_title ; 1,3-Bis(diarylmethylene)-2-methylenecyclohexanes in cycloaddition and cyclodimerization reactions. The role of stereoelectronic factors ; #============================================================================== data_B210890A _database_code_CSD 169688 _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2-hydroxy-6-(4-methoxybencyliden)-2-[1-(4-methoxyphenyl)ethyl]cyclohexanone ; _chemical_name_common ;2-hydroxy-6-(4-methoxybencyliden)-2-(1-(4- methoxyphenyl)ethyl)cyclohexanone ; _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C23 H26 O4' _chemical_formula_weight 366.44 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P2(1)/c ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 12.915(2) _cell_length_b 5.6940(10) _cell_length_c 27.080(3) _cell_angle_alpha 90.00 _cell_angle_beta 98.69 _cell_angle_gamma 90.00 _cell_volume 1968.5(5) _cell_formula_units_Z 4 _cell_measurement_temperature 291(2) _cell_measurement_reflns_used 38 _cell_measurement_theta_min 7.21 _cell_measurement_theta_max 27.71 _exptl_crystal_description 'Prism laminar' _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas NO _exptl_crystal_density_diffrn 1.236 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 784 _exptl_absorpt_coefficient_mu 0.671 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 291(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Siemens P4/PC' _diffrn_measurement_method 'q/2\q scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 97 _diffrn_standards_decay_% >2 _diffrn_reflns_number 3740 _diffrn_reflns_av_R_equivalents 0.0281 _diffrn_reflns_av_sigmaI/netI 0.0353 _diffrn_reflns_limit_h_min -1 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -1 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 3.30 _diffrn_reflns_theta_max 56.70 _reflns_number_total 2626 _reflns_number_gt 2154 _reflns_threshold_expression >2\s(I) _computing_data_collection 'XSCANS v2.1b (SIEMENS Software 1993)' _computing_cell_refinement 'XSCANS v2.1b (SIEMENS Software 1993)' _computing_data_reduction 'XSCANS v2.1b (SIEMENS software 1993)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XP (SHELXTL PC: SIEMENS, 1990)' _computing_publication_material 'SHELXTL PC: (SIEMENS,1990)' _solved_by 'Simon Hernandez-Ortega' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0534P)^2^+0.3373P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment 'No Refined except H2 on O2' _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0041(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2626 _refine_ls_number_parameters 248 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0533 _refine_ls_R_factor_gt 0.0423 _refine_ls_wR_factor_ref 0.1124 _refine_ls_wR_factor_gt 0.1037 _refine_ls_goodness_of_fit_ref 1.041 _refine_ls_restrained_S_all 1.041 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 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 _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.38470(12) 0.8757(3) -0.03569(5) 0.0633(5) Uani 1 1 d . . . O2 O 0.38044(14) 1.1018(3) 0.05081(7) 0.0642(5) Uani 1 1 d . . . H2 H 0.424(2) 1.079(6) 0.0377(11) 0.077 Uiso 1 1 d . . . O3 O -0.00682(14) -0.0765(3) -0.20623(7) 0.0791(6) Uani 1 1 d . . . O4 O 0.34329(15) 0.7181(4) 0.28170(6) 0.0868(6) Uani 1 1 d . . . C1 C 0.31172(16) 0.8254(4) -0.01370(7) 0.0489(5) Uani 1 1 d . . . C2 C 0.31522(16) 0.9020(4) 0.04073(8) 0.0485(5) Uani 1 1 d . . . C3 C 0.20587(18) 0.9743(4) 0.04962(9) 0.0635(6) Uani 1 1 d . . . H3A H 0.2074 1.0088 0.0848 0.076 Uiso 1 1 calc R . . H3B H 0.1855 1.1166 0.0309 0.076 Uiso 1 1 calc R . . C4 C 0.12482(17) 0.7852(5) 0.03409(9) 0.0661(7) Uani 1 1 d . . . H4A H 0.0572 0.8377 0.0413 0.079 Uiso 1 1 calc R . . H4B H 0.1438 0.6442 0.0534 0.079 Uiso 1 1 calc R . . C5 C 0.11624(18) 0.7281(5) -0.02134(9) 0.0651(7) Uani 1 1 d . . . H5A H 0.0726 0.5900 -0.0285 0.078 Uiso 1 1 calc R . . H5B H 0.0820 0.8577 -0.0405 0.078 Uiso 1 1 calc R . . C6 C 0.22099(16) 0.6839(4) -0.03791(7) 0.0484(5) Uani 1 1 d . . . C7 C 0.35927(15) 0.6875(4) 0.07342(7) 0.0436(5) Uani 1 1 d . . . H7 H 0.3176 0.5502 0.0610 0.052 Uiso 1 1 calc R . . C8 C 0.24015(15) 0.5293(4) -0.07258(7) 0.0480(5) Uani 1 1 d . . . H8 H 0.3103 0.5172 -0.0764 0.058 Uiso 1 1 calc R . . C9 C 0.47284(17) 0.6353(4) 0.06748(8) 0.0543(5) Uani 1 1 d . . . H9A H 0.4782 0.6200 0.0326 0.065 Uiso 1 1 calc R . . H9B H 0.4947 0.4915 0.0844 0.065 Uiso 1 1 calc R . . H9C H 0.5169 0.7615 0.0816 0.065 Uiso 1 1 calc R . . C10 C 0.16961(15) 0.3756(4) -0.10558(7) 0.0483(5) Uani 1 1 d . . . C11 C 0.21028(17) 0.1710(4) -0.12397(8) 0.0554(6) Uani 1 1 d . . . H11 H 0.2803 0.1335 -0.1137 0.066 Uiso 1 1 calc R . . C12 C 0.15009(18) 0.0243(4) -0.15666(9) 0.0613(6) Uani 1 1 d . . . H12 H 0.1792 -0.1112 -0.1679 0.074 Uiso 1 1 calc R . . C13 C 0.04574(18) 0.0778(4) -0.17293(8) 0.0566(6) Uani 1 1 d . . . C14 C 0.00344(17) 0.2806(5) -0.15612(8) 0.0596(6) Uani 1 1 d . . . H14 H -0.0663 0.3184 -0.1670 0.072 Uiso 1 1 calc R . . C15 C 0.06506(17) 0.4270(4) -0.12300(8) 0.0579(6) Uani 1 1 d . . . H15 H 0.0359 0.5633 -0.1121 0.070 Uiso 1 1 calc R . . C16 C 0.35100(15) 0.7115(4) 0.12835(7) 0.0449(5) Uani 1 1 d . . . C17 C 0.39925(18) 0.8920(4) 0.15767(8) 0.0576(6) Uani 1 1 d . . . H17 H 0.4332 1.0102 0.1426 0.069 Uiso 1 1 calc R . . C18 C 0.39827(19) 0.9012(5) 0.20887(8) 0.0615(6) Uani 1 1 d . . . H18 H 0.4310 1.0245 0.2276 0.074 Uiso 1 1 calc R . . C19 C 0.34885(17) 0.7279(5) 0.23170(8) 0.0596(6) Uani 1 1 d . . . C20 C 0.30072(19) 0.5464(5) 0.20344(8) 0.0649(7) Uani 1 1 d . . . H20 H 0.2674 0.4281 0.2188 0.078 Uiso 1 1 calc R . . C21 C 0.30152(17) 0.5388(4) 0.15262(8) 0.0552(6) Uani 1 1 d . . . H21 H 0.2682 0.4153 0.1341 0.066 Uiso 1 1 calc R . . C22 C -0.1114(2) -0.0188(6) -0.22714(11) 0.0837(9) Uani 1 1 d . . . H22A H -0.1395 -0.1404 -0.2499 0.100 Uiso 1 1 calc R . . H22B H -0.1119 0.1275 -0.2448 0.100 Uiso 1 1 calc R . . H22C H -0.1534 -0.0047 -0.2009 0.100 Uiso 1 1 calc R . . C23 C 0.3900(3) 0.9007(7) 0.31255(10) 0.0996(11) Uani 1 1 d . . . H23A H 0.3802 0.8717 0.3465 0.120 Uiso 1 1 calc R . . H23B H 0.3581 1.0476 0.3016 0.120 Uiso 1 1 calc R . . H23C H 0.4636 0.9068 0.3106 0.120 Uiso 1 1 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_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0540(9) 0.0785(11) 0.0564(9) 0.0071(8) 0.0056(7) -0.0155(8) O2 0.0727(11) 0.0435(9) 0.0743(11) -0.0060(8) 0.0046(8) -0.0090(9) O3 0.0675(11) 0.0759(12) 0.0878(12) -0.0263(10) -0.0083(9) -0.0010(10) O4 0.0807(12) 0.1351(18) 0.0475(9) -0.0176(10) 0.0189(8) -0.0263(12) C1 0.0471(12) 0.0476(12) 0.0501(11) 0.0054(10) 0.0012(10) 0.0012(10) C2 0.0494(11) 0.0405(11) 0.0540(12) -0.0039(9) 0.0023(9) 0.0000(10) C3 0.0615(14) 0.0591(14) 0.0677(14) -0.0113(12) 0.0030(11) 0.0151(12) C4 0.0460(12) 0.0840(18) 0.0693(14) -0.0142(13) 0.0119(11) 0.0105(12) C5 0.0447(12) 0.0844(18) 0.0653(14) -0.0135(13) 0.0052(10) 0.0048(12) C6 0.0407(11) 0.0569(13) 0.0466(11) 0.0024(10) 0.0033(9) 0.0023(10) C7 0.0451(11) 0.0392(11) 0.0455(10) -0.0058(9) 0.0034(8) -0.0015(9) C8 0.0392(10) 0.0594(13) 0.0448(11) 0.0015(10) 0.0043(8) 0.0013(10) C9 0.0526(12) 0.0589(13) 0.0514(11) -0.0007(10) 0.0080(9) 0.0072(11) C10 0.0412(11) 0.0587(13) 0.0448(10) 0.0041(10) 0.0057(9) 0.0004(10) C11 0.0452(11) 0.0621(14) 0.0567(12) 0.0015(11) 0.0005(10) 0.0095(11) C12 0.0590(14) 0.0560(14) 0.0666(14) -0.0078(11) 0.0022(11) 0.0109(11) C13 0.0544(13) 0.0583(14) 0.0554(12) -0.0043(11) 0.0026(10) -0.0017(11) C14 0.0412(11) 0.0723(16) 0.0628(13) -0.0088(12) -0.0004(10) 0.0037(11) C15 0.0470(12) 0.0645(15) 0.0606(13) -0.0112(11) 0.0028(10) 0.0079(11) C16 0.0396(10) 0.0449(11) 0.0493(11) -0.0056(9) 0.0041(8) -0.0008(9) C17 0.0639(13) 0.0564(13) 0.0532(12) -0.0083(11) 0.0112(10) -0.0148(12) C18 0.0610(13) 0.0674(15) 0.0555(13) -0.0187(12) 0.0068(10) -0.0090(13) C19 0.0485(12) 0.0832(17) 0.0482(12) -0.0118(12) 0.0111(10) -0.0008(12) C20 0.0644(14) 0.0784(17) 0.0539(13) -0.0003(12) 0.0161(11) -0.0165(13) C21 0.0561(12) 0.0551(13) 0.0542(12) -0.0092(10) 0.0082(10) -0.0125(11) C22 0.0575(15) 0.101(2) 0.0879(18) -0.0236(17) -0.0058(13) -0.0144(15) C23 0.0858(19) 0.156(3) 0.0573(15) -0.0388(19) 0.0127(14) -0.012(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.222(3) . yes O2 C2 1.417(3) . yes O3 C13 1.364(3) . yes O3 C22 1.422(3) . yes O4 C19 1.368(3) . yes O4 C23 1.411(4) . yes C1 C6 1.490(3) . yes C1 C2 1.531(3) . yes C2 C3 1.525(3) . yes C2 C7 1.564(3) . yes C3 C4 1.516(4) . yes C4 C5 1.523(3) . yes C5 C6 1.509(3) . yes C6 C8 1.337(3) . yes C7 C16 1.513(3) . yes C7 C9 1.529(3) . yes C8 C10 1.466(3) . yes C10 C15 1.392(3) . yes C10 C11 1.400(3) . yes C11 C12 1.370(3) . yes C12 C13 1.387(3) . yes C13 C14 1.383(3) . yes C14 C15 1.385(3) . yes C16 C17 1.388(3) . yes C16 C21 1.391(3) . yes C17 C18 1.389(3) . yes C18 C19 1.372(4) . yes C19 C20 1.377(3) . yes C20 C21 1.379(3) . yes loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C13 O3 C22 117.6(2) . . yes C19 O4 C23 118.3(2) . . yes O1 C1 C6 121.70(19) . . yes O1 C1 C2 119.30(19) . . yes C6 C1 C2 118.97(18) . . yes O2 C2 C3 106.89(18) . . yes O2 C2 C1 110.12(17) . . yes C3 C2 C1 109.60(17) . . yes O2 C2 C7 111.28(16) . . yes C3 C2 C7 112.83(18) . . yes C1 C2 C7 106.14(16) . . yes C4 C3 C2 112.43(19) . . yes C3 C4 C5 111.7(2) . . yes C6 C5 C4 113.17(18) . . yes C8 C6 C1 116.63(18) . . yes C8 C6 C5 126.0(2) . . yes C1 C6 C5 117.36(19) . . yes C16 C7 C9 109.41(16) . . yes C16 C7 C2 114.34(16) . . yes C9 C7 C2 111.41(17) . . yes C6 C8 C10 131.09(19) . . yes C15 C10 C11 116.8(2) . . yes C15 C10 C8 124.2(2) . . yes C11 C10 C8 118.79(18) . . yes C12 C11 C10 122.0(2) . . yes C11 C12 C13 120.0(2) . . yes O3 C13 C14 125.0(2) . . yes O3 C13 C12 115.5(2) . . yes C14 C13 C12 119.5(2) . . yes C13 C14 C15 119.9(2) . . yes C14 C15 C10 121.7(2) . . yes C17 C16 C21 116.87(19) . . yes C17 C16 C7 122.48(19) . . yes C21 C16 C7 120.41(18) . . yes C16 C17 C18 121.9(2) . . yes C19 C18 C17 119.8(2) . . yes O4 C19 C18 125.0(2) . . yes O4 C19 C20 115.6(2) . . yes C18 C19 C20 119.4(2) . . yes C19 C20 C21 120.5(2) . . yes C20 C21 C16 121.5(2) . . yes loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O2 H2 O1 0.72(3) 2.29(3) 2.681(2) 116(3) . O2 H2 O1 0.72(3) 2.50(3) 3.124(2) 147(3) 3_675 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 56.70 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.137 _refine_diff_density_min -0.149 _refine_diff_density_rms 0.035