# Supplementary Material (ESI) for Perkin Transactions # This journal is © The Royal Society of Chemistry 2000 # CCDC Number: 207/397 # Asymmetric synthesis of the northern segment of ephedradine C data_compound_13 _audit_creation_date 1999-09-17 _audit_creation_method 'cif4actac using rusm095a.cif' _chemical_formula_moiety 'C18 H17 Br1 O5' _chemical_formula_sum 'C18 H17 Br1 O5' _chemical_formula_weight 393.242 _exptl_absorpt_coefficient_mu 3.50 _exptl_absorpt_correction_T_max ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_type none _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.527 _exptl_crystal_density_meas ? _exptl_crystal_density_method ? _exptl_crystal_description 'elongated rod' _exptl_crystal_size_max 0.6 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.08 _exptl_crystal_size_rad ? _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 11.094(2) _cell_length_b 28.750(2) _cell_length_c 5.363(3) _cell_measurement_reflns_used 25 _cell_measurement_temperature 294 _cell_measurement_theta_max 39.76 _cell_measurement_theta_min 38.53 _cell_volume 1711.(1) _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.541838 _diffrn_measurement_device 'Rigaku AFC5 diffractometer' _diffrn_measurement_device_type ? _diffrn_measurement_method 'theta/2theta scans' _diffrn_reflns_av_R_equivalents 0.035 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_k_max 35 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_number 3228 _diffrn_reflns_theta_max 71 _diffrn_standards_decay_% -3.(2) _diffrn_standards_interval_count 400 _diffrn_standards_interval_time ? _diffrn_standards_number 3 _refine_diff_density_max 0.42(9) _refine_diff_density_min -.41(9) _refine_ls_R_factor_gt 0.0446 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_gt 1.168 _refine_ls_hydrogen_treatment noref _refine_ls_number_parameters 220 _refine_ls_number_reflns 3219 _refine_ls_restrained_S_all 1.055 _refine_ls_shift/su_max -.003 _refine_ls_structure_factor_coef Fsqd _refine_ls_wR_factor_gt 0.156 _refine_ls_weighting_scheme sigma _reflns_number_gt 2600 _reflns_number_total 3228 _reflns_threshold_expression '>2sigma(I)' _computing_cell_refinement 'Molecular Structure Corp. AFC5 software' _computing_data_collection 'Molecular Structure Corp. AFC5 software' _computing_data_reduction 'locally developed software' _computing_molecular_graphics 'ORTEP (Johnson, 1965) & PLUTO (Motherwell and Clegg)' _computing_publication_material 'locally developed software' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 199?)' _computing_structure_solution 'SHELXS86 (Sheldrick, 1990)' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+ 1/2, -y, z+ 1/2' 'x+ 1/2, -y+ 1/2, -z' '-x, y+ 1/2, -z+ 1/2' loop_ _atom_site_label _atom_site_chemical_conn_number _atom_site_type_symbol _atom_site_occupancy _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_thermal_displace_type _atom_site_attached_hydrogens _atom_site_calc_attached_atom _atom_site_calc_flag _atom_site_constraints _atom_site_description _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_refinement_flags _atom_site_restraints _atom_site_symmetry_multiplicity Br10 1 Br 1 -0.89108(6) -0.23595(3) -0.9314(1) 0.070203(4) Uani ? ? ? ? ? ? ? ? ? ? O1 2 O 1 -1.3101(3) -0.1757(1) -1.5507(8) 0.0528(1) Uani ? ? ? ? ? ? ? ? ? ? O20 3 O 1 -1.8315(3) -0.0952(2) -1.564(1) 0.0740(2) Uani ? ? ? ? ? ? ? ? ? ? O22 4 O 1 -1.6837(4) -0.0508(2) -1.8394(9) 0.0618(2) Uani ? ? ? ? ? ? ? ? ? ? O25 5 O 1 -1.1610(4) -0.0771(1) -0.9383(9) 0.0684(2) Uani ? ? ? ? ? ? ? ? ? ? O26 6 O 1 -1.1941(6) -0.0507(2) -1.316(1) 0.0894(4) Uani ? ? ? ? ? ? ? ? ? ? C2 7 C 1 -1.3334(4) -0.1285(2) -1.459(1) 0.0421(2) Uani ? ? ? ? ? ? ? ? ? ? C3 8 C 1 -1.2723(5) -0.1261(2) -1.200(1) 0.0427(2) Uani ? ? ? ? ? ? ? ? ? ? C4 9 C 1 -1.1860(4) -0.1664(2) -1.212(1) 0.0409(2) Uani ? ? ? ? ? ? ? ? ? ? C5 10 C 1 -1.0926(4) -0.1798(2) -1.057(1) 0.0445(2) Uani ? ? ? ? ? ? ? ? ? ? C6 11 C 1 -1.0287(5) -0.2200(2) -1.122(1) 0.0531(3) Uani ? ? ? ? ? ? ? ? ? ? C7 12 C 1 -1.0604(5) -0.2471(2) -1.322(1) 0.0546(2) Uani ? ? ? ? ? ? ? ? ? ? C8 13 C 1 -1.1560(5) -0.2339(2) -1.476(1) 0.0549(2) Uani ? ? ? ? ? ? ? ? ? ? C9 14 C 1 -1.2151(4) -0.1930(2) -1.417(1) 0.0444(2) Uani ? ? ? ? ? ? ? ? ? ? C11 15 C 1 -1.4658(4) -0.1195(2) -1.471(1) 0.0428(2) Uani ? ? ? ? ? ? ? ? ? ? C12 16 C 1 -1.5090(4) -0.0882(2) -1.649(1) 0.0441(2) Uani ? ? ? ? ? ? ? ? ? ? C13 17 C 1 -1.6325(5) -0.0808(2) -1.674(1) 0.0468(2) Uani ? ? ? ? ? ? ? ? ? ? C14 18 C 1 -1.7119(4) -0.1045(2) -1.523(1) 0.0515(3) Uani ? ? ? ? ? ? ? ? ? ? C15 19 C 1 -1.6698(5) -0.1355(2) -1.346(1) 0.0561(3) Uani ? ? ? ? ? ? ? ? ? ? C16 20 C 1 -1.5465(4) -0.1425(2) -1.320(1) 0.0485(2) Uani ? ? ? ? ? ? ? ? ? ? C21 21 C 1 -1.9164(6) -0.1198(3) -1.420(2) 0.0852(7) Uani ? ? ? ? ? ? ? ? ? ? C23 22 C 1 -1.6081(6) -0.0253(2) -2.000(1) 0.0675(4) Uani ? ? ? ? ? ? ? ? ? ? C24 23 C 1 -1.2082(5) -0.0802(2) -1.163(1) 0.0474(2) Uani ? ? ? ? ? ? ? ? ? ? C27 24 C 1 -1.0893(8) -0.0359(2) -0.885(1) 0.0828(7) Uani ? ? ? ? ? ? ? ? ? ? H2 25 H 1 -1.2927(4) -0.1064(2) -1.569(1) 0.050580 Uiso ? ? ? ? ? ? ? ? ? ? H3 26 H 1 -1.3318(5) -0.1311(2) -1.067(1) 0.051190 Uiso ? ? ? ? ? ? ? ? ? ? H5 27 H 1 -1.0731(4) -0.1628(2) -0.915(1) 0.053450 Uiso ? ? ? ? ? ? ? ? ? ? H7 28 H 1 -1.0180(5) -0.2743(2) -1.356(1) 0.065500 Uiso ? ? ? ? ? ? ? ? ? ? H8 29 H 1 -1.1791(5) -0.2519(2) -1.612(1) 0.065850 Uiso ? ? ? ? ? ? ? ? ? ? H12 30 H 1 -1.4552(4) -0.0722(2) -1.751(1) 0.052980 Uiso ? ? ? ? ? ? ? ? ? ? H15 31 H 1 -1.7237(5) -0.1515(2) -1.245(1) 0.067270 Uiso ? ? ? ? ? ? ? ? ? ? H16 32 H 1 -1.5182(4) -0.1629(2) -1.199(1) 0.058250 Uiso ? ? ? ? ? ? ? ? ? ? H21A 33 H 1 -1.9960(7) -0.109(2) -1.458(9) 0.127830 Uiso ? ? ? ? ? ? ? ? ? ? H21B 34 H 1 -1.900(3) -0.115(2) -1.246(2) 0.127830 Uiso ? ? ? ? ? ? ? ? ? ? H21C 35 H 1 -1.911(4) -0.1524(4) -1.457(9) 0.127830 Uiso ? ? ? ? ? ? ? ? ? ? H23A 36 H 1 -1.6564(6) -0.006(1) -2.107(7) 0.101300 Uiso ? ? ? ? ? ? ? ? ? ? H23B 37 H 1 -1.562(3) -0.0463(2) -2.100(7) 0.101300 Uiso ? ? ? ? ? ? ? ? ? ? H23C 38 H 1 -1.555(3) -0.006(1) -1.903(1) 0.101300 Uiso ? ? ? ? ? ? ? ? ? ? H27A 39 H 1 -1.011(2) -0.039(1) -0.96(1) 0.124160 Uiso ? ? ? ? ? ? ? ? ? ? H27B 40 H 1 -1.081(5) -0.032(1) -0.708(1) 0.124160 Uiso ? ? ? ? ? ? ? ? ? ? H27C 41 H 1 -1.129(3) -0.0089(4) -0.95(1) 0.124160 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 Br10 0.0586(3) 0.0824(4) 0.0696(4) 0.0244(3) 0.0000(3) 0.0177(4) O1 0.042(2) 0.057(2) 0.060(2) 0.010(2) -0.006(2) -0.016(2) O20 0.034(2) 0.075(3) 0.114(4) 0.008(2) 0.016(2) 0.030(3) O22 0.046(2) 0.065(2) 0.074(3) 0.013(2) 0.008(2) 0.028(2) O25 0.093(3) 0.053(2) 0.060(2) -0.024(2) -0.013(3) 0.004(2) O26 0.139(5) 0.052(2) 0.077(3) -0.017(3) -0.022(3) 0.015(2) C2 0.037(2) 0.048(3) 0.041(3) 0.004(2) -0.001(2) -0.006(2) C3 0.040(2) 0.043(2) 0.045(3) 0.004(2) 0.006(2) 0.000(2) C4 0.038(2) 0.037(2) 0.048(3) 0.002(2) 0.007(2) 0.005(2) C5 0.045(3) 0.040(2) 0.048(3) 0.002(2) 0.001(3) 0.006(2) C6 0.051(3) 0.048(3) 0.061(4) 0.007(2) 0.008(2) 0.013(2) C7 0.055(3) 0.045(3) 0.064(4) 0.011(2) 0.012(3) 0.002(3) C8 0.051(3) 0.051(3) 0.062(4) 0.005(2) 0.005(2) -0.008(3) C9 0.036(2) 0.050(3) 0.047(3) 0.001(2) 0.007(2) -0.004(2) C11 0.039(2) 0.039(2) 0.051(3) 0.000(2) 0.002(2) 0.000(2) C12 0.038(2) 0.045(2) 0.049(3) 0.004(2) 0.011(2) 0.001(2) C13 0.047(3) 0.039(2) 0.055(3) 0.007(2) 0.006(2) 0.007(2) C14 0.038(3) 0.046(3) 0.071(4) 0.006(2) 0.012(2) 0.005(3) C15 0.045(3) 0.047(3) 0.076(4) -0.001(2) 0.015(3) 0.016(3) C16 0.041(3) 0.044(3) 0.061(3) 0.005(2) 0.004(2) 0.012(3) C21 0.042(3) 0.090(5) 0.124(7) -0.002(3) 0.020(4) 0.032(5) C23 0.065(4) 0.058(3) 0.079(5) 0.004(3) 0.007(4) 0.021(3) C24 0.054(3) 0.039(2) 0.050(3) 0.005(2) -0.003(2) -0.005(2) C27 0.110(6) 0.063(4) 0.076(5) -0.034(4) -0.020(5) -0.003(3) loop_ _chemical_conn_bond_atom_1 _chemical_conn_bond_atom_2 _chemical_conn_bond_type 1 11 sing 2 7 sing 3 21 sing 4 22 sing 5 24 sing 7 8 sing 7 15 sing 7 25 sing 8 9 sing 8 23 sing 8 26 sing 9 10 sing 10 27 sing 11 10 doub 11 12 sing 12 13 doub 12 28 sing 13 14 sing 13 29 sing 14 2 sing 14 9 doub 15 16 sing 15 20 doub 16 17 doub 16 30 sing 17 4 sing 17 18 sing 18 3 sing 18 19 doub 19 20 sing 19 31 sing 20 32 sing 21 33 sing 21 34 sing 21 35 sing 22 36 sing 22 37 sing 22 38 sing 23 5 sing 23 6 doub 24 39 sing 24 40 sing 24 41 sing 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 Br10 C6 1.894(6) . ? O1 C9 1.368(6) . ? O1 C2 1.468(6) . ? O20 C14 1.370(6) . ? O20 C21 1.408(8) . ? O22 C13 1.361(6) . ? O22 C23 1.410(7) . ? O25 C24 1.314(7) . ? O25 C27 1.456(7) . ? O26 C24 1.194(7) . ? C2 C11 1.493(6) . ? C2 C3 1.547(8) . ? C3 C4 1.503(6) . ? C3 C24 1.513(7) . ? C4 C9 1.377(8) . ? C4 C5 1.383(7) . ? C5 C6 1.400(7) . ? C6 C7 1.374(9) . ? C7 C8 1.394(8) . ? C8 C9 1.384(7) . ? C11 C16 1.376(7) . ? C11 C12 1.398(7) . ? C12 C13 1.393(7) . ? C13 C14 1.377(7) . ? C14 C15 1.384(8) . ? C15 C16 1.390(7) . ? 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 C9 O1 C2 107.2(4) . . ? C14 O20 C21 117.6(5) . . ? C13 O22 C23 118.7(5) . . ? C24 O25 C27 116.9(5) . . ? O1 C2 C11 108.6(4) . . ? O1 C2 C3 105.3(4) . . ? C11 C2 C3 117.6(5) . . ? C4 C3 C24 112.2(4) . . ? C4 C3 C2 101.9(4) . . ? C24 C3 C2 111.2(5) . . ? C9 C4 C5 120.1(5) . . ? C9 C4 C3 108.2(4) . . ? C5 C4 C3 131.7(5) . . ? C4 C5 C6 117.3(5) . . ? C7 C6 C5 122.3(5) . . ? C7 C6 Br10 119.4(4) . . ? C5 C6 Br10 118.2(5) . . ? C6 C7 C8 120.0(5) . . ? C9 C8 C7 117.3(5) . . ? O1 C9 C4 113.5(4) . . ? O1 C9 C8 123.6(5) . . ? C4 C9 C8 122.9(5) . . ? C16 C11 C12 119.3(5) . . ? C16 C11 C2 122.1(5) . . ? C12 C11 C2 118.6(5) . . ? C13 C12 C11 120.0(5) . . ? O22 C13 C14 115.4(5) . . ? O22 C13 C12 124.7(5) . . ? C14 C13 C12 119.9(5) . . ? O20 C14 C13 115.5(5) . . ? O20 C14 C15 124.1(5) . . ? C13 C14 C15 120.4(5) . . ? C14 C15 C16 119.6(5) . . ? C11 C16 C15 120.8(5) . . ? O26 C24 O25 122.1(5) . . ? O26 C24 C3 126.2(6) . . ? O25 C24 C3 111.5(5) . . ? _publ_contact_author_name 'R.G. Ball' _publ_contact_author_address ; Merck Research Laboratories POB 2000, MS:R50-105 Rahway, NJ USA 07065 ; _publ_contact_author_email 'Richard_Ball@merck.com' _publ_contact_author_fax 908-594-6793 _publ_contact_author_phone 908-594-5341 #===END data_compound_17 _audit_creation_date 1999-09-13 _audit_creation_method 'cif4actac using rusm099a.cif' _chemical_formula_moiety 'C24 H29 N1 O7' _chemical_formula_sum 'C24 H29 N1 O7' _chemical_formula_weight 443.501 _exptl_absorpt_coefficient_mu 0.70 _exptl_absorpt_correction_T_max ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_type none _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.218 _exptl_crystal_density_meas ? _exptl_crystal_density_method none _exptl_crystal_description plate _exptl_crystal_size_max 0.275 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.04 _exptl_crystal_size_rad ? _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 11.799(4) _cell_length_b 25.651(6) _cell_length_c 7.991(6) _cell_measurement_reflns_used 19 _cell_measurement_temperature 294 _cell_measurement_theta_max 11.65 _cell_measurement_theta_min 9.13 _cell_volume 2419.(3) _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.541838 _diffrn_measurement_device 'Rigaku AFC5 diffractometer' _diffrn_measurement_device_type ? _diffrn_measurement_method 'theta/2theta scans' _diffrn_reflns_av_R_equivalents 0. _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_k_max 31 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_number 2482 _diffrn_reflns_theta_max 70.37 _diffrn_standards_decay_% 1.8(9) _diffrn_standards_interval_count 400 _diffrn_standards_interval_time ? _diffrn_standards_number 3 _refine_diff_density_max 0.26 _refine_diff_density_min -0.23 _refine_ls_R_factor_gt 0.069 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_gt 1.272 _refine_ls_hydrogen_treatment constr _refine_ls_number_parameters 289 _refine_ls_number_reflns 2480 _refine_ls_restrained_S_all 0.982 _refine_ls_shift/su_max -0.001 _refine_ls_structure_factor_coef Fsqd _refine_ls_wR_factor_gt 0.166 _refine_ls_weighting_scheme 'calc w=1/[\s^2^(Fo^2^)+( 0.1024P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _reflns_number_gt 885 _reflns_number_total 2482 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement 'Molecular Structure Corp. AFC5 software' _computing_data_collection 'Molecular Structure Corp. AFC5 software' _computing_data_reduction 'locally developed software' _computing_molecular_graphics 'ORTEP (Johnson, 1965) & PLUTO (Motherwell and Clegg)' _computing_publication_material 'locally developed software' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'O' 'O' 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' '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' loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 'x, y, z' 2 '-x+ 1/2, -y, z+ 1/2' 3 'x+ 1/2, -y+ 1/2, -z' 4 '-x, y+ 1/2, -z+ 1/2' 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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group O1 O 0.5634(6) 0.1407(3) 0.1116(9) 0.062(2) Uani 1 d . . O16 O 0.9863(6) 0.0294(3) -0.1717(10) 0.077(3) Uani 1 d . . O18 O 0.8806(7) 0.0790(4) -0.4044(10) 0.101(3) Uani 1 d . . O21 O 0.3471(8) 0.0931(3) -0.2348(11) 0.087(3) Uani 1 d . . O22 O 0.3212(7) 0.0143(3) -0.1346(9) 0.071(2) Uani 1 d . . O27 O 0.1052(10) 0.2465(4) 0.4380(14) 0.134(5) Uani 1 d . . O28 O 0.0283(8) 0.1829(3) 0.2730(12) 0.088(3) Uani 1 d . . N24 N 0.1638(7) 0.0686(3) 0.5781(10) 0.066(3) Uani 1 d . . H24A H 0.2396(7) 0.0787(3) 0.6378(10) 0.079 Uiso 1 d R . H24B H 0.0996(7) 0.0662(3) 0.6175(10) 0.079 Uiso 1 d R . H24C H 0.1766(7) 0.0532(3) 0.4717(10) 0.079 Uiso 1 d R . C2 C 0.5475(9) 0.1066(4) -0.0337(12) 0.053(3) Uani 1 d . . H2 H 0.5247(9) 0.1283(4) -0.1287(12) 0.064 Uiso 1 calc R . C3 C 0.4499(9) 0.0692(4) 0.0058(12) 0.050(3) Uani 1 d . . H3 H 0.4814(9) 0.0363(4) 0.0480(12) 0.060 Uiso 1 calc R . C4 C 0.3969(8) 0.0987(4) 0.1497(11) 0.046(3) Uani 1 d . . C5 C 0.2919(8) 0.0903(4) 0.2275(12) 0.050(3) Uani 1 d . . H5 H 0.2433(8) 0.0644(4) 0.1884(12) 0.060 Uiso 1 calc R . C6 C 0.2619(9) 0.1200(4) 0.3598(14) 0.058(3) Uani 1 d . . C7 C 0.3364(11) 0.1582(5) 0.4172(14) 0.071(3) Uani 1 d . . H7 H 0.3157(11) 0.1784(5) 0.5088(14) 0.085 Uiso 1 calc R . C8 C 0.4417(11) 0.1669(4) 0.3405(13) 0.068(3) Uani 1 d . . H8 H 0.4929(11) 0.1913(4) 0.3815(13) 0.082 Uiso 1 calc R . C9 C 0.4647(9) 0.1374(4) 0.2022(11) 0.049(3) Uani 1 d . . C10 C 0.6614(9) 0.0829(4) -0.0737(12) 0.051(3) Uani 1 d . . C11 C 0.7145(10) 0.0524(4) 0.0407(14) 0.063(3) Uani 1 d . . H11 H 0.6775(10) 0.0442(4) 0.1401(14) 0.075 Uiso 1 calc R . C12 C 0.8237(10) 0.0330(5) 0.0124(14) 0.067(3) Uani 1 d . . H12 H 0.8601(10) 0.0125(5) 0.0921(14) 0.081 Uiso 1 calc R . C13 C 0.8758(9) 0.0451(4) -0.1372(14) 0.057(3) Uani 1 d . . C14 C 0.8210(9) 0.0737(5) -0.2568(14) 0.069(3) Uani 1 d . . C15 C 0.7159(9) 0.0924(4) -0.2274(14) 0.062(3) Uani 1 d . . H15 H 0.6792(9) 0.1117(4) -0.3095(14) 0.074 Uiso 1 calc R . C17 C 1.0445(10) 0.0021(5) -0.0447(16) 0.093(4) Uani 1 d . . H17A H 1.1193(10) -0.0065(5) -0.0830(16) 0.140 Uiso 1 calc R . H17B H 1.0041(10) -0.0293(5) -0.0182(16) 0.140 Uiso 1 calc R . H17C H 1.0498(10) 0.0236(5) 0.0533(16) 0.140 Uiso 1 calc R . C19 C 0.8216(14) 0.1025(7) -0.5423(15) 0.128(6) Uani 1 d . . H19A H 0.8710(14) 0.1041(7) -0.6376(15) 0.191 Uiso 1 calc R . H19B H 0.7983(14) 0.1371(7) -0.5120(15) 0.191 Uiso 1 calc R . H19C H 0.7561(14) 0.0820(7) -0.5695(15) 0.191 Uiso 1 calc R . C20 C 0.3666(10) 0.0571(5) -0.1365(14) 0.060(3) Uani 1 d . . C23 C 0.1506(10) 0.1123(4) 0.4472(13) 0.061(3) Uani 1 d . . H23 H 0.0960(10) 0.1001(4) 0.3634(13) 0.074 Uiso 1 calc R . C25 C 0.0975(11) 0.1583(4) 0.5374(14) 0.082(4) Uani 1 d . . H25A H 0.1473(11) 0.1701(4) 0.6262(14) 0.098 Uiso 1 calc R . H25B H 0.0259(11) 0.1479(4) 0.5870(14) 0.098 Uiso 1 calc R . C26 C 0.0780(12) 0.2026(6) 0.4099(20) 0.083(4) Uani 1 d . . C29 C 0.0019(15) 0.2176(6) 0.1230(20) 0.102(5) Uani 1 d . . C30 C 0.1193(17) 0.2381(7) 0.0563(22) 0.156(8) Uani 1 d . . H30A H 0.1669(17) 0.2090(7) 0.0287(22) 0.234 Uiso 1 calc R . H30B H 0.1552(17) 0.2587(7) 0.1412(22) 0.234 Uiso 1 calc R . H30C H 0.1073(17) 0.2590(7) -0.0417(22) 0.234 Uiso 1 calc R . C31 C -0.0768(13) 0.2596(5) 0.1686(19) 0.115(5) Uani 1 d . . H31A H -0.0404(13) 0.2830(5) 0.2454(19) 0.172 Uiso 1 calc R . H31B H -0.1430(13) 0.2449(5) 0.2205(19) 0.172 Uiso 1 calc R . H31C H -0.0987(13) 0.2783(5) 0.0698(19) 0.172 Uiso 1 calc R . C32 C -0.0464(22) 0.1780(8) 0.0016(21) 0.185(9) Uani 1 d . . H32A H 0.0098(22) 0.1519(8) -0.0220(21) 0.277 Uiso 1 calc R . H32B H -0.0676(22) 0.1952(8) -0.1003(21) 0.277 Uiso 1 calc R . H32C H -0.1119(22) 0.1618(8) 0.0503(21) 0.277 Uiso 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 0.057(4) 0.064(5) 0.065(5) -0.018(4) 0.017(4) -0.010(4) O16 0.050(5) 0.114(7) 0.068(5) -0.007(5) 0.016(4) 0.012(5) O18 0.074(5) 0.176(9) 0.052(5) 0.009(6) 0.024(5) 0.019(6) O21 0.106(7) 0.088(6) 0.068(5) 0.032(5) -0.034(6) -0.014(6) O22 0.085(6) 0.066(5) 0.061(5) 0.002(5) -0.016(5) -0.009(5) O27 0.130(10) 0.094(7) 0.177(13) -0.038(8) 0.012(9) 0.030(8) O28 0.107(8) 0.059(5) 0.100(7) 0.006(6) 0.017(7) 0.025(6) N24 0.052(5) 0.096(7) 0.050(5) 0.005(5) 0.009(5) -0.002(5) C2 0.062(7) 0.055(7) 0.042(6) -0.001(5) 0.004(6) -0.005(6) C3 0.048(6) 0.055(6) 0.048(6) 0.016(5) 0.006(6) 0.009(6) C4 0.047(6) 0.054(7) 0.037(6) -0.010(6) 0.011(5) 0.012(6) C5 0.054(6) 0.058(7) 0.037(6) -0.007(6) 0.003(6) 0.010(6) C6 0.055(7) 0.057(7) 0.061(8) 0.015(7) -0.005(6) 0.008(6) C7 0.077(9) 0.078(8) 0.057(7) -0.019(7) 0.018(8) 0.011(7) C8 0.071(8) 0.078(8) 0.055(7) -0.034(7) 0.011(7) -0.020(7) C9 0.057(7) 0.050(6) 0.039(6) -0.003(5) 0.000(6) -0.006(6) C10 0.052(7) 0.060(7) 0.040(6) -0.001(6) 0.015(6) 0.002(6) C11 0.063(8) 0.082(8) 0.044(7) 0.018(6) 0.017(6) 0.009(7) C12 0.051(7) 0.092(9) 0.059(7) 0.019(7) 0.014(7) 0.010(7) C13 0.033(6) 0.087(9) 0.050(7) -0.011(7) 0.012(6) 0.003(6) C14 0.045(6) 0.116(10) 0.047(7) -0.003(7) 0.021(6) 0.010(8) C15 0.057(7) 0.079(8) 0.050(7) -0.011(7) 0.000(6) 0.009(7) C17 0.050(8) 0.141(12) 0.089(10) 0.020(10) 0.002(7) 0.024(9) C19 0.118(12) 0.212(18) 0.052(8) 0.034(11) -0.002(9) -0.030(14) C20 0.065(8) 0.073(8) 0.042(7) -0.004(7) 0.018(7) 0.016(7) C23 0.084(8) 0.052(7) 0.048(6) 0.004(6) 0.020(7) 0.020(6) C25 0.082(9) 0.096(10) 0.067(8) -0.007(8) 0.005(8) 0.041(8) C26 0.084(10) 0.065(9) 0.099(11) -0.018(9) 0.006(9) 0.024(8) C29 0.129(14) 0.073(10) 0.102(12) 0.013(10) -0.010(11) 0.039(10) C30 0.176(21) 0.147(16) 0.144(17) 0.072(14) 0.064(16) 0.052(14) C31 0.101(11) 0.114(11) 0.129(13) 0.024(11) 0.011(11) 0.024(10) C32 0.282(29) 0.160(17) 0.113(13) -0.007(15) -0.040(19) 0.007(20) 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 C9 1.375(12) . ? O1 C2 1.466(11) . ? O16 C13 1.391(11) . ? O16 C17 1.411(13) . ? O18 C14 1.380(13) . ? O18 C19 1.436(15) . ? O21 C20 1.235(12) . ? O22 C20 1.222(13) . ? O27 C26 1.19(2) . ? O28 C26 1.34(2) . ? O28 C29 1.524(15) . ? N24 C23 1.540(12) . ? C2 C10 1.510(14) . ? C2 C3 1.531(14) . ? C3 C4 1.512(13) . ? C3 C20 1.535(15) . ? C4 C9 1.344(13) . ? C4 C5 1.403(13) . ? C5 C6 1.350(14) . ? C6 C7 1.394(14) . ? C6 C23 1.501(15) . ? C7 C8 1.404(15) . ? C8 C9 1.366(13) . ? C10 C11 1.356(13) . ? C10 C15 1.407(14) . ? C11 C12 1.401(15) . ? C12 C13 1.380(14) . ? C13 C14 1.368(15) . ? C14 C15 1.349(14) . ? C23 C25 1.518(13) . ? C25 C26 1.54(2) . ? C29 C31 1.47(2) . ? C29 C32 1.52(2) . ? C29 C30 1.57(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 C9 O1 C2 105.8(7) . . ? C13 O16 C17 117.2(9) . . ? C14 O18 C19 116.8(9) . . ? C26 O28 C29 120.7(10) . . ? O1 C2 C10 107.1(8) . . ? O1 C2 C3 107.9(8) . . ? C10 C2 C3 117.5(8) . . ? C4 C3 C2 98.9(8) . . ? C4 C3 C20 113.5(8) . . ? C2 C3 C20 117.1(9) . . ? C9 C4 C5 120.0(9) . . ? C9 C4 C3 111.2(9) . . ? C5 C4 C3 128.8(10) . . ? C6 C5 C4 119.5(10) . . ? C5 C6 C7 119.3(10) . . ? C5 C6 C23 121.3(11) . . ? C7 C6 C23 119.4(11) . . ? C6 C7 C8 121.8(10) . . ? C9 C8 C7 116.1(10) . . ? C4 C9 C8 123.0(10) . . ? C4 C9 O1 112.6(8) . . ? C8 C9 O1 124.1(10) . . ? C11 C10 C15 118.5(10) . . ? C11 C10 C2 120.0(9) . . ? C15 C10 C2 121.5(10) . . ? C10 C11 C12 121.4(10) . . ? C13 C12 C11 118.0(11) . . ? C14 C13 C12 121.0(10) . . ? C14 C13 O16 117.4(10) . . ? C12 C13 O16 121.6(11) . . ? C15 C14 C13 120.2(10) . . ? C15 C14 O18 125.6(12) . . ? C13 C14 O18 114.1(10) . . ? C14 C15 C10 120.7(11) . . ? O22 C20 O21 126.8(12) . . ? O22 C20 C3 117.0(11) . . ? O21 C20 C3 116.1(11) . . ? C6 C23 C25 118.7(10) . . ? C6 C23 N24 108.9(8) . . ? C25 C23 N24 106.5(8) . . ? C23 C25 C26 108.7(9) . . ? O27 C26 O28 128.9(15) . . ? O27 C26 C25 122.1(15) . . ? O28 C26 C25 109.0(11) . . ? C31 C29 C32 114.4(16) . . ? C31 C29 O28 111.2(13) . . ? C32 C29 O28 100.9(11) . . ? C31 C29 C30 113.3(13) . . ? C32 C29 C30 109.7(16) . . ? O28 C29 C30 106.3(12) . . ? _publ_contact_author_name 'R.G. Ball' _publ_contact_author_address ; Merck Research Laboratories POB 2000, MS:R50-105 Rahway, NJ USA 07065 ; _publ_contact_author_email 'Richard_Ball@merck.com' _publ_contact_author_fax 908-594-6793 _publ_contact_author_phone 908-594-5341 #===END