# Supplementary Material (ESI) for Perkin Transactions # This journal is © The Royal Society of Chemistry 2002 data_jw2k _database_code_CSD 189923 _audit_creation_method 'manual editing of SHELXL-97 cif' _journal_coden_Cambridge 207 loop_ _publ_author_name _publ_author_address 'Babu, B. Ravindra' ; Department of Chemistry University of Southern Denmark DK-5230 Odense M Denmark ; 'Prasad, Ashok K.' ; Department of Chemistry University of Southern Denmark DK-5230 Odense M Denmark ; 'Trikha, Smriti' ; Department of Chemistry University of Southern Denmark DK-5230 Odense M Denmark ; 'Thorup, Niels' ; Department of Chemistry Technical University of Denmark DK-2800 Lyngby Denmark ; 'Virinder, S. Parmar' ; Department of Chemistry University of Delhi Delhi 110 007 India ; 'Wengel, Jesper' ; Department of Chemistry University of Southern Denmark DK-5230 Odense M Denmark ; _publ_contact_author_name 'Prof Jesper Wengel' _publ_contact_author_address ; Department of Chemistry University of Southern Denmark Nucleic Acid Center Campusvej 55 Odense M DK-5230 DENMARK ; _publ_contact_author_email 'JWE@CHEM.SDU.DK' _publ_contact_author_fax '+45 4588 3136' _publ_contact_author_phone '+45 4525 2028' _journal_name_full ; Journal of the Chemical Society, Perkin Transactions 1 ; _publ_section_title ; Conformationally locked aryl C-nucleosides: Synthesis of phosphoramidite monomers and incorporation into single-stranded DNA and LNA (locked nucleic acid) ; _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H14 O4' _chemical_formula_weight 222.23 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' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 1 21 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 9.2257(12) _cell_length_b 6.1948(8) _cell_length_c 9.5781(12) _cell_angle_alpha 90.00 _cell_angle_beta 108.220(2) _cell_angle_gamma 90.00 _cell_volume 519.96(12) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 976 _cell_measurement_theta_min 2.24 _cell_measurement_theta_max 29.91 _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.43 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.419 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 236 _exptl_absorpt_coefficient_mu 0.106 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9578 _exptl_absorpt_correction_T_max 0.9880 _exptl_absorpt_process_details 'SABABS (Sheldrick, 2000)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Siemens/Bruker SMART 1K)' _diffrn_measurement_method 'omega scan, frame data integration' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6577 _diffrn_reflns_av_R_equivalents 0.0248 _diffrn_reflns_av_sigmaI/netI 0.0332 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.24 _diffrn_reflns_theta_max 29.97 _reflns_number_total 2705 _reflns_number_gt 2436 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0561P)^2^+0.0000P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.0(7) _refine_ls_number_reflns 2705 _refine_ls_number_parameters 201 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0405 _refine_ls_R_factor_gt 0.0346 _refine_ls_wR_factor_ref 0.0853 _refine_ls_wR_factor_gt 0.0823 _refine_ls_goodness_of_fit_ref 1.032 _refine_ls_restrained_S_all 1.031 _refine_ls_shift/su_max 0.001 _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 C1 C 0.22529(16) 0.4540(2) 0.47678(14) 0.0166(3) Uani 1 1 d . . . C2 C 0.23203(16) 0.3024(3) 0.37257(15) 0.0213(3) Uani 1 1 d . . . C3 C 0.31841(17) 0.3398(3) 0.28018(16) 0.0255(3) Uani 1 1 d . . . C4 C 0.39776(17) 0.5329(3) 0.29103(16) 0.0256(3) Uani 1 1 d . . . C5 C 0.39106(17) 0.6852(3) 0.39302(16) 0.0240(3) Uani 1 1 d . . . C6 C 0.30486(16) 0.6459(2) 0.48718(16) 0.0200(3) Uani 1 1 d . . . C1' C 0.13157(15) 0.4008(2) 0.57631(14) 0.0160(3) Uani 1 1 d . . . C2' C 0.20233(15) 0.2282(2) 0.69097(14) 0.0164(3) Uani 1 1 d . . . C3' C 0.30709(14) 0.3647(2) 0.81440(13) 0.0140(3) Uani 1 1 d . . . C4' C 0.17307(15) 0.5101(2) 0.81733(14) 0.0148(3) Uani 1 1 d . . . C5' C 0.19964(16) 0.6972(2) 0.92032(15) 0.0181(3) Uani 1 1 d . . . C5'' C 0.06093(16) 0.3393(3) 0.83638(15) 0.0189(3) Uani 1 1 d . . . O2' O 0.08832(11) 0.15654(17) 0.75399(11) 0.0205(2) Uani 1 1 d . . . O3' O 0.36773(12) 0.24450(16) 0.94554(10) 0.0170(2) Uani 1 1 d . . . O4' O 0.11951(11) 0.58355(15) 0.66706(10) 0.0163(2) Uani 1 1 d . . . O5' O 0.33496(12) 0.80952(18) 0.92074(11) 0.0216(2) Uani 1 1 d . . . H1 H 0.1802(19) 0.157(3) 0.3684(19) 0.022(4) Uiso 1 1 d . . . H2 H 0.321(2) 0.233(3) 0.215(2) 0.026(5) Uiso 1 1 d . . . H3 H 0.455(2) 0.563(3) 0.226(2) 0.031(5) Uiso 1 1 d . . . H4 H 0.445(2) 0.819(4) 0.4066(19) 0.024(4) Uiso 1 1 d . . . H5 H 0.301(2) 0.749(3) 0.560(2) 0.026(5) Uiso 1 1 d . . . H6 H 0.0262(18) 0.353(3) 0.5152(17) 0.015(4) Uiso 1 1 d . . . H7 H 0.2435(17) 0.101(3) 0.6576(17) 0.012(4) Uiso 1 1 d . . . H8 H 0.3799(17) 0.446(3) 0.7875(16) 0.011(4) Uiso 1 1 d . . . H9 H 0.0801(18) 0.298(3) 0.9375(17) 0.016(4) Uiso 1 1 d . . . H10 H -0.0498(17) 0.390(3) 0.7934(17) 0.012(4) Uiso 1 1 d . . . H11 H 0.2098(19) 0.639(3) 1.022(2) 0.024(4) Uiso 1 1 d . . . H12 H 0.113(2) 0.796(3) 0.8877(18) 0.020(4) Uiso 1 1 d . . . H13 H 0.461(2) 0.267(4) 0.979(2) 0.033(5) Uiso 1 1 d . . . H14 H 0.325(3) 0.941(4) 0.927(2) 0.044(6) Uiso 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 C1 0.0121(6) 0.0208(7) 0.0147(6) 0.0022(5) 0.0010(5) 0.0001(5) C2 0.0190(7) 0.0247(7) 0.0181(6) -0.0017(6) 0.0028(5) -0.0027(6) C3 0.0241(7) 0.0359(9) 0.0157(6) -0.0044(7) 0.0051(5) -0.0015(7) C4 0.0203(7) 0.0382(9) 0.0181(6) 0.0046(6) 0.0057(5) -0.0010(7) C5 0.0199(7) 0.0260(8) 0.0239(7) 0.0063(6) 0.0038(5) -0.0033(6) C6 0.0193(6) 0.0199(7) 0.0198(6) -0.0002(6) 0.0046(5) -0.0004(6) C1' 0.0147(6) 0.0173(7) 0.0153(6) -0.0019(5) 0.0038(5) -0.0008(5) C2' 0.0167(6) 0.0139(6) 0.0178(6) 0.0002(5) 0.0043(5) -0.0009(5) C3' 0.0151(6) 0.0120(6) 0.0143(6) 0.0002(5) 0.0037(5) 0.0018(5) C4' 0.0130(6) 0.0160(6) 0.0149(6) 0.0028(5) 0.0039(5) 0.0024(5) C5' 0.0193(6) 0.0171(7) 0.0183(6) 0.0010(5) 0.0066(5) 0.0037(5) C5'' 0.0170(6) 0.0196(7) 0.0207(6) 0.0032(6) 0.0065(5) 0.0002(6) O2' 0.0203(5) 0.0180(5) 0.0230(5) 0.0015(4) 0.0066(4) -0.0049(4) O3' 0.0153(5) 0.0159(5) 0.0172(4) 0.0034(4) 0.0011(4) 0.0008(4) O4' 0.0185(5) 0.0160(5) 0.0136(4) 0.0011(3) 0.0037(3) 0.0029(4) O5' 0.0196(5) 0.0140(5) 0.0275(5) -0.0024(4) 0.0019(4) 0.0000(4) _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 C1 C6 1.385(2) . ? C1 C2 1.386(2) . ? C1 C1' 1.5100(18) . ? C2 C3 1.383(2) . ? C2 H1 1.02(2) . ? C3 C4 1.389(3) . ? C3 H2 0.91(2) . ? C4 C5 1.373(2) . ? C4 H3 0.950(18) . ? C5 C6 1.398(2) . ? C5 H4 0.96(2) . ? C6 H5 0.95(2) . ? C1' O4' 1.4524(16) . ? C1' C2' 1.5257(18) . ? C1' H6 1.010(16) . ? C2' O2' 1.4369(16) . ? C2' C3' 1.5271(18) . ? C2' H7 0.972(17) . ? C3' O3' 1.4162(15) . ? C3' C4' 1.5371(18) . ? C3' H8 0.939(16) . ? C4' O4' 1.4416(15) . ? C4' C5' 1.4920(19) . ? C4' C5'' 1.530(2) . ? C5' O5' 1.4280(17) . ? C5' H11 1.014(18) . ? C5' H12 0.975(19) . ? C5'' O2' 1.4469(18) . ? C5'' H9 0.964(16) . ? C5'' H10 1.024(15) . ? O3' H13 0.83(2) . ? O5' H14 0.82(2) . ? 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 C6 C1 C2 119.44(13) . . ? C6 C1 C1' 122.49(12) . . ? C2 C1 C1' 118.06(13) . . ? C3 C2 C1 120.78(15) . . ? C3 C2 H1 118.8(10) . . ? C1 C2 H1 120.2(10) . . ? C2 C3 C4 119.48(15) . . ? C2 C3 H2 117.2(11) . . ? C4 C3 H2 123.3(11) . . ? C5 C4 C3 120.32(14) . . ? C5 C4 H3 119.0(12) . . ? C3 C4 H3 120.6(12) . . ? C4 C5 C6 120.04(15) . . ? C4 C5 H4 123.8(10) . . ? C6 C5 H4 116.2(10) . . ? C1 C6 C5 119.93(14) . . ? C1 C6 H5 119.3(11) . . ? C5 C6 H5 120.7(11) . . ? O4' C1' C1 111.97(11) . . ? O4' C1' C2' 102.19(10) . . ? C1 C1' C2' 113.99(11) . . ? O4' C1' H6 109.6(10) . . ? C1 C1' H6 109.6(9) . . ? C2' C1' H6 109.2(10) . . ? O2' C2' C1' 108.32(11) . . ? O2' C2' C3' 102.42(10) . . ? C1' C2' C3' 101.18(10) . . ? O2' C2' H7 107.4(9) . . ? C1' C2' H7 117.1(9) . . ? C3' C2' H7 119.1(9) . . ? O3' C3' C2' 111.99(11) . . ? O3' C3' C4' 112.88(10) . . ? C2' C3' C4' 91.18(10) . . ? O3' C3' H8 114.1(9) . . ? C2' C3' H8 114.8(9) . . ? C4' C3' H8 109.8(10) . . ? O4' C4' C5' 110.43(11) . . ? O4' C4' C5'' 107.69(11) . . ? C5' C4' C5'' 115.84(11) . . ? O4' C4' C3' 101.15(9) . . ? C5' C4' C3' 120.04(11) . . ? C5'' C4' C3' 100.06(11) . . ? O5' C5' C4' 110.06(11) . . ? O5' C5' H11 110.7(10) . . ? C4' C5' H11 107.6(11) . . ? O5' C5' H12 108.8(11) . . ? C4' C5' H12 109.1(11) . . ? H11 C5' H12 110.7(14) . . ? O2' C5'' C4' 103.66(10) . . ? O2' C5'' H9 109.3(11) . . ? C4' C5'' H9 112.7(10) . . ? O2' C5'' H10 110.1(9) . . ? C4' C5'' H10 111.5(9) . . ? H9 C5'' H10 109.4(12) . . ? C2' O2' C5'' 105.25(10) . . ? C3' O3' H13 108.9(15) . . ? C4' O4' C1' 106.56(10) . . ? C5' O5' H14 111.3(16) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 0.7(2) . . . . ? C1' C1 C2 C3 -178.71(13) . . . . ? C1 C2 C3 C4 -0.8(2) . . . . ? C2 C3 C4 C5 0.2(2) . . . . ? C3 C4 C5 C6 0.4(2) . . . . ? C2 C1 C6 C5 0.0(2) . . . . ? C1' C1 C6 C5 179.32(13) . . . . ? C4 C5 C6 C1 -0.5(2) . . . . ? C6 C1 C1' O4' 7.72(17) . . . . ? C2 C1 C1' O4' -172.93(12) . . . . ? C6 C1 C1' C2' -107.67(15) . . . . ? C2 C1 C1' C2' 71.68(15) . . . . ? O4' C1' C2' O2' 72.43(12) . . . . ? C1 C1' C2' O2' -166.57(11) . . . . ? O4' C1' C2' C3' -34.81(12) . . . . ? C1 C1' C2' C3' 86.20(13) . . . . ? O2' C2' C3' O3' 58.18(13) . . . . ? C1' C2' C3' O3' 169.99(10) . . . . ? O2' C2' C3' C4' -57.15(11) . . . . ? C1' C2' C3' C4' 54.66(11) . . . . ? O3' C3' C4' O4' -171.23(11) . . . . ? C2' C3' C4' O4' -56.70(11) . . . . ? O3' C3' C4' C5' 67.10(15) . . . . ? C2' C3' C4' C5' -178.36(12) . . . . ? O3' C3' C4' C5'' -60.78(13) . . . . ? C2' C3' C4' C5'' 53.76(11) . . . . ? O4' C4' C5' O5' -73.89(13) . . . . ? C5'' C4' C5' O5' 163.38(11) . . . . ? C3' C4' C5' O5' 43.09(15) . . . . ? O4' C4' C5'' O2' 70.73(13) . . . . ? C5' C4' C5'' O2' -165.11(11) . . . . ? C3' C4' C5'' O2' -34.50(12) . . . . ? C1' C2' O2' C5'' -67.73(13) . . . . ? C3' C2' O2' C5'' 38.65(13) . . . . ? C4' C5'' O2' C2' -2.10(13) . . . . ? C5' C4' O4' C1' 166.73(11) . . . . ? C5'' C4' O4' C1' -65.90(12) . . . . ? C3' C4' O4' C1' 38.56(12) . . . . ? C1 C1' O4' C4' -124.80(11) . . . . ? C2' C1' O4' C4' -2.41(12) . . . . ? _diffrn_measured_fraction_theta_max 0.928 _diffrn_reflns_theta_full 29.97 _diffrn_measured_fraction_theta_full 0.928 _refine_diff_density_max 0.240 _refine_diff_density_min -0.271 _refine_diff_density_rms 0.047