# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_coden_Cambridge 182 _journal_volume ? _journal_page_first ? _journal_year ? loop_ _publ_author_name 'Tsutomu Inokuchi' 'Li-Jian Ma.' _publ_contact_author_name 'Tsutomu Inokuchi' _publ_contact_author_email inokuchi@cc.okayama-u.ac.jp _publ_section_title ; Solvent-free micorowave-assisted multi-component reaction for preparation of 2-aminoketones as precursors of pseudoephedrine analogues ; # Attachment '15b.CIF.txt' #------------------------------------------------------------------------------ data_ma _database_code_depnum_ccdc_archive 'CCDC 772789' #TrackingRef '15b.CIF.txt' #------------------------------------------------------------------------------ # CHEMICAL DATA _chemical_formula_sum 'C18 H24 Br N O2 ' _chemical_formula_moiety 'C18 H24 Br N O2 ' _chemical_formula_weight 366.30 _chemical_melting_point ? #------------------------------------------------------------------------------ # CRYSTAL DATA _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1 ' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z _cell_length_a 10.3812(5) _cell_length_b 11.6853(3) _cell_length_c 8.0564(5) _cell_angle_alpha 100.735(4) _cell_angle_beta 108.601(4) _cell_angle_gamma 103.438(2) _cell_volume 864.20(8) _cell_formula_units_Z 2 _cell_measurement_reflns_used 2469 _cell_measurement_theta_min 3.3 _cell_measurement_theta_max 25.3 _cell_measurement_temperature 296.2 #------------------------------------------------------------------------------ _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.700 _exptl_crystal_size_mid 0.300 _exptl_crystal_size_min 0.250 _exptl_crystal_size_rad ? _exptl_crystal_density_diffrn 1.408 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_absorpt_coefficient_mu 2.392 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(Higashi, 1995)' _exptl_absorpt_correction_T_min 0.328 _exptl_absorpt_correction_T_max 0.550 #------------------------------------------------------------------------------ # EXPERIMENTAL DATA _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.7107 _diffrn_measurement_device_type 'Rigaku RAXIS-IV Imaging Plate' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 10.00 _diffrn_reflns_number 3384 _diffrn_reflns_av_R_equivalents 0.028 _diffrn_reflns_theta_max 25.35 _diffrn_measured_fraction_theta_max 0.9139 _diffrn_reflns_theta_full 25.35 _diffrn_measured_fraction_theta_full 0.9139 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 #------------------------------------------------------------------------------ # REFINEMENT DATA _refine_special_details ; Refinement using reflections with F^2^ > 0.0 sigma(F^2^). The weighted R-factor (wR), goodness of fit (S) and R-factor (gt) are based on F, with F set to zero for negative F. The threshold expression of F^2^ > 2.0 sigma(F^2^) is used only for calculating R-factor (gt). ; _reflns_number_total 2889 _reflns_number_gt 2461 _reflns_threshold_expression F^2^>2.0\s(F^2^) _refine_ls_structure_factor_coef F _refine_ls_R_factor_gt 0.0696 _refine_ls_wR_factor_ref 0.1247 _refine_ls_hydrogen_treatment noref _refine_ls_number_reflns 2737 _refine_ls_number_parameters 199 _refine_ls_goodness_of_fit_ref 1.542 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[\s^2^(Fo) + 0.00497|Fo|^2^]' _refine_ls_shift/su_max 0.0083 _refine_diff_density_max 0.98 _refine_diff_density_min -0.64 _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details ? _refine_ls_abs_structure_Flack ? 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 6.1.1.1) ; H H 0.000 0.000 ;International Tables for Crystallography (1992, Vol. C, Table 6.1.1.2) ; O O 0.011 0.006 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; N N 0.006 0.003 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; Br Br -0.290 2.459 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; #------------------------------------------------------------------------------ # ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS 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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Br(1) Br 0.16160(6) -0.52167(5) 0.37110(9) 0.0929(3) Uani 1.00 d . . . O(2) O 0.8670(4) 0.2203(4) 0.1035(5) 0.079(1) Uani 1.00 d . . . O(3) O 0.7608(3) -0.0364(3) 0.5709(3) 0.0690(8) Uani 1.00 d . . . N(2) N 0.7720(3) 0.0228(3) 0.2455(4) 0.0528(8) Uani 1.00 d . . . C(2) C 0.6623(4) -0.0881(4) 0.2346(5) 0.0486(9) Uani 1.00 d . . . C(3) C 0.6317(4) -0.0691(4) 0.4126(5) 0.0543(10) Uani 1.00 d . . . C(4) C 0.3073(5) -0.3833(4) 0.3896(6) 0.062(1) Uani 1.00 d . . . C(5) C 0.3812(4) -0.2104(4) 0.2870(5) 0.055(1) Uani 1.00 d . . . C(6) C 0.5228(4) -0.1790(4) 0.4105(5) 0.0502(9) Uani 1.00 d . . . C(7) C 0.4471(5) -0.3540(4) 0.5139(6) 0.066(1) Uani 1.00 d . . . C(8) C 0.7028(4) -0.2021(4) 0.1866(5) 0.0508(10) Uani 1.00 d . . . C(9) C 0.5519(5) -0.2542(5) 0.5249(5) 0.063(1) Uani 1.00 d . . . C(10) C 0.6189(5) -0.2923(5) 0.0310(5) 0.064(1) Uani 1.00 d . . . C(11) C 0.8084(6) 0.0043(5) 0.0830(8) 0.074(1) Uani 1.00 d . . . C(13) C 0.8405(5) -0.2125(5) 0.3128(6) 0.065(1) Uani 1.00 d . . . C(14) C 0.6527(7) -0.4056(5) -0.0326(7) 0.084(2) Uani 1.00 d . . . C(15) C 0.7228(5) 0.1310(5) 0.2580(6) 0.068(1) Uani 1.00 d . . . C(16) C 0.9174(7) 0.1175(6) 0.0909(10) 0.089(2) Uani 1.00 d . . . C(17) C 0.8321(7) 0.2409(5) 0.2613(7) 0.080(1) Uani 1.00 d . . . C(18) C 0.8903(6) -0.3099(7) 0.2212(7) 0.087(2) Uani 1.00 d . . . C(19) C 0.7691(8) -0.4263(6) 0.1140(8) 0.093(2) Uani 1.00 d . . . C(20) C 0.2761(5) -0.3101(4) 0.2748(6) 0.061(1) Uani 1.00 d . . . H(1) H 0.3575 -0.1606 0.2090 0.0934 Uiso 1.00 calc . . . H(2) H 0.4698 -0.4042 0.5916 0.1074 Uiso 1.00 calc . . . H(3) H 0.6462 -0.2353 0.6118 0.0694 Uiso 1.00 calc . . . H(5) H 0.5938 -0.0026 0.4209 0.0468 Uiso 1.00 calc . . . H(6) H 0.8465 -0.0622 0.0758 0.0867 Uiso 1.00 calc . . . H(7) H 0.7245 -0.0140 -0.0228 0.1035 Uiso 1.00 calc . . . H(8) H 0.6369 0.1140 0.1552 0.0688 Uiso 1.00 calc . . . H(9) H 0.7043 0.1480 0.3665 0.0709 Uiso 1.00 calc . . . H(10) H 0.9384 0.1030 -0.0163 0.1074 Uiso 1.00 calc . . . H(11) H 1.0025 0.1346 0.1950 0.1196 Uiso 1.00 calc . . . H(12) H 0.9162 0.2597 0.3663 0.0803 Uiso 1.00 calc . . . H(13) H 0.7951 0.3080 0.2656 0.1196 Uiso 1.00 calc . . . H(14) H 0.5764 -0.0962 0.1377 0.1063 Uiso 1.00 calc . . . H(18) H 0.5681 -0.4741 -0.0736 0.0658 Uiso 1.00 calc . . . H(19) H 0.6819 -0.3993 -0.1319 0.0913 Uiso 1.00 calc . . . H(20) H 0.9304 -0.2799 0.1415 0.1266 Uiso 1.00 calc . . . H(21) H 0.9613 -0.3273 0.3131 0.1223 Uiso 1.00 calc . . . H(22) H 0.7300 -0.4575 0.1951 0.1410 Uiso 1.00 calc . . . H(23) H 0.8044 -0.4849 0.0599 0.1121 Uiso 1.00 calc . . . H(24) H 0.5324 -0.2823 -0.0427 0.0768 Uiso 1.00 calc . . . H(25) H 0.9132 -0.1357 0.3518 0.0926 Uiso 1.00 calc . . . H(26) H 0.8259 -0.2327 0.4156 0.0800 Uiso 1.00 calc . . . H(27) H 0.1818 -0.3294 0.1883 0.1063 Uiso 1.00 calc . . . H(28) H 0.8168 -0.0044 0.5370 0.1213 Uiso 1.00 calc . . . 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 Br(1) 0.0980(6) 0.0625(5) 0.1316(7) 0.0126(3) 0.0701(5) 0.0276(4) O(2) 0.084(2) 0.072(2) 0.078(2) 0.014(2) 0.030(2) 0.032(2) O(3) 0.063(2) 0.076(2) 0.046(1) 0.005(2) 0.013(1) 0.002(1) N(2) 0.048(2) 0.053(2) 0.054(2) 0.012(1) 0.019(1) 0.011(1) C(2) 0.046(2) 0.050(2) 0.051(2) 0.018(2) 0.019(1) 0.013(2) C(3) 0.055(2) 0.050(2) 0.055(2) 0.015(2) 0.024(2) 0.003(2) C(4) 0.070(2) 0.052(2) 0.076(2) 0.018(2) 0.045(2) 0.017(2) C(5) 0.057(2) 0.057(2) 0.060(2) 0.025(2) 0.028(2) 0.021(2) C(6) 0.057(2) 0.044(2) 0.050(2) 0.017(2) 0.025(2) 0.004(1) C(7) 0.080(3) 0.056(2) 0.074(2) 0.029(2) 0.037(2) 0.023(2) C(8) 0.055(2) 0.053(2) 0.047(2) 0.020(2) 0.023(2) 0.013(2) C(9) 0.065(2) 0.068(3) 0.055(2) 0.028(2) 0.016(2) 0.020(2) C(10) 0.061(2) 0.068(3) 0.053(2) 0.024(2) 0.015(2) 0.002(2) C(11) 0.084(3) 0.067(3) 0.093(3) 0.026(2) 0.055(3) 0.026(2) C(13) 0.052(2) 0.075(3) 0.067(2) 0.029(2) 0.017(2) 0.013(2) C(14) 0.104(4) 0.074(3) 0.070(3) 0.040(3) 0.031(3) 0.001(2) C(15) 0.077(3) 0.052(2) 0.072(2) 0.015(2) 0.031(2) 0.012(2) C(16) 0.084(3) 0.086(4) 0.115(4) 0.024(3) 0.052(3) 0.044(3) C(17) 0.092(3) 0.056(3) 0.081(3) 0.012(2) 0.026(3) 0.017(2) C(18) 0.081(3) 0.120(5) 0.080(3) 0.064(4) 0.031(3) 0.031(3) C(19) 0.131(5) 0.078(4) 0.084(3) 0.061(4) 0.044(3) 0.017(3) C(20) 0.057(2) 0.062(3) 0.066(2) 0.018(2) 0.028(2) 0.012(2) #------------------------------------------------------------------------------ _computing_data_collection PROCESS-AUTO _computing_cell_refinement PROCESS-AUTO _computing_data_reduction 'teXsan Ver. 1.11' _computing_structure_solution SIR97 _computing_structure_refinement 'teXsan Ver. 1.10' _computing_publication_material 'teXsan Ver. 1.11' _computing_molecular_graphics ? #------------------------------------------------------------------------------ _geom_special_details ; ? ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag Br(1) C(4) 1.889(5) . . yes O(2) C(16) 1.419(8) . . yes O(2) C(17) 1.420(8) . . yes O(3) C(3) 1.435(5) . . yes N(2) C(2) 1.481(5) . . yes N(2) C(11) 1.471(6) . . yes N(2) C(15) 1.469(6) . . yes C(2) C(3) 1.555(5) . . yes C(2) C(8) 1.507(5) . . yes C(3) C(6) 1.494(6) . . yes C(4) C(7) 1.394(7) . . yes C(4) C(20) 1.381(7) . . yes C(5) C(6) 1.402(6) . . yes C(5) C(20) 1.359(6) . . yes C(6) C(9) 1.400(6) . . yes C(7) C(9) 1.362(7) . . yes C(8) C(10) 1.348(6) . . yes C(8) C(13) 1.516(6) . . yes C(10) C(14) 1.493(7) . . yes C(11) C(16) 1.502(8) . . yes C(13) C(18) 1.518(7) . . yes C(14) C(19) 1.503(9) . . yes C(15) C(17) 1.493(8) . . yes C(18) C(19) 1.50(1) . . 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C(16) O(2) C(17) 109.6(4) . . . yes C(2) N(2) C(11) 110.6(3) . . . yes C(2) N(2) C(15) 112.1(3) . . . yes C(11) N(2) C(15) 107.4(4) . . . yes N(2) C(2) C(3) 109.6(3) . . . yes N(2) C(2) C(8) 111.4(3) . . . yes C(3) C(2) C(8) 114.4(3) . . . yes O(3) C(3) C(2) 110.8(3) . . . yes O(3) C(3) C(6) 111.2(3) . . . yes C(2) C(3) C(6) 112.0(3) . . . yes Br(1) C(4) C(7) 121.3(3) . . . yes Br(1) C(4) C(20) 119.7(3) . . . yes C(7) C(4) C(20) 119.0(4) . . . yes C(6) C(5) C(20) 122.4(4) . . . yes C(3) C(6) C(5) 118.9(3) . . . yes C(3) C(6) C(9) 124.3(4) . . . yes C(5) C(6) C(9) 116.8(4) . . . yes C(4) C(7) C(9) 120.8(4) . . . yes C(2) C(8) C(10) 120.3(3) . . . yes C(2) C(8) C(13) 119.0(3) . . . yes C(10) C(8) C(13) 120.7(4) . . . yes C(6) C(9) C(7) 121.0(4) . . . yes C(8) C(10) C(14) 124.5(4) . . . yes N(2) C(11) C(16) 111.0(5) . . . yes C(8) C(13) C(18) 112.8(4) . . . yes C(10) C(14) C(19) 112.5(4) . . . yes N(2) C(15) C(17) 111.5(4) . . . yes O(2) C(16) C(11) 111.4(5) . . . yes O(2) C(17) C(15) 111.8(4) . . . yes C(13) C(18) C(19) 111.6(5) . . . yes C(14) C(19) C(18) 111.8(5) . . . yes C(4) C(20) C(5) 119.9(4) . . . yes #------------------------------------------------------------------------------ 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 Br(1) C(4) C(7) C(9) 179.6(4) . . . . yes Br(1) C(4) C(20) C(5) -179.7(3) . . . . yes O(2) C(16) C(11) N(2) -59.1(6) . . . . yes O(2) C(17) C(15) N(2) 58.2(6) . . . . yes O(3) C(3) C(2) N(2) -54.6(4) . . . . yes O(3) C(3) C(2) C(8) 71.2(4) . . . . yes O(3) C(3) C(6) C(5) 168.0(3) . . . . yes O(3) C(3) C(6) C(9) -11.8(5) . . . . yes N(2) C(2) C(3) C(6) -179.3(3) . . . . yes N(2) C(2) C(8) C(10) -118.2(4) . . . . yes N(2) C(2) C(8) C(13) 60.2(4) . . . . yes C(2) N(2) C(11) C(16) 178.9(4) . . . . yes C(2) N(2) C(15) C(17) -177.6(4) . . . . yes C(2) C(3) C(6) C(5) -67.6(5) . . . . yes C(2) C(3) C(6) C(9) 112.7(4) . . . . yes C(2) C(8) C(10) C(14) 177.2(5) . . . . yes C(2) C(8) C(13) C(18) -162.2(4) . . . . yes C(3) C(2) N(2) C(11) 176.9(3) . . . . yes C(3) C(2) N(2) C(15) -63.3(4) . . . . yes C(3) C(2) C(8) C(10) 116.9(4) . . . . yes C(3) C(2) C(8) C(13) -64.6(5) . . . . yes C(3) C(6) C(5) C(20) 179.2(4) . . . . yes C(3) C(6) C(9) C(7) -179.3(4) . . . . yes C(4) C(7) C(9) C(6) -0.8(7) . . . . yes C(4) C(20) C(5) C(6) 1.1(6) . . . . yes C(5) C(6) C(9) C(7) 1.0(6) . . . . yes C(5) C(20) C(4) C(7) -0.9(6) . . . . yes C(6) C(3) C(2) C(8) -53.5(4) . . . . yes C(8) C(2) N(2) C(11) 49.4(4) . . . . yes C(8) C(2) N(2) C(15) 169.2(3) . . . . yes C(8) C(10) C(14) C(19) 14.8(9) . . . . yes C(8) C(13) C(18) C(19) -44.8(6) . . . . yes C(9) C(6) C(5) C(20) -1.1(6) . . . . yes C(9) C(7) C(4) C(20) 0.8(7) . . . . yes C(10) C(8) C(13) C(18) 16.2(7) . . . . yes C(10) C(14) C(19) C(18) -43.3(8) . . . . yes C(11) N(2) C(15) C(17) -55.9(5) . . . . yes C(11) C(16) O(2) C(17) 58.1(6) . . . . yes C(13) C(8) C(10) C(14) -1.2(8) . . . . yes C(13) C(18) C(19) C(14) 59.6(7) . . . . yes C(15) N(2) C(11) C(16) 56.2(5) . . . . yes C(15) C(17) O(2) C(16) -57.7(6) . . . . yes C(15) C(17) O(2) C(16) -57.7(6) . . . . yes #------------------------------------------------------------------------------ loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 _geom_contact_publ_flag Br(1) O(2) 3.490(4) . 1_445 ? Br(1) C(17) 3.596(6) . 1_445 ? O(2) C(5) 3.333(5) . 2_655 ? O(2) C(20) 3.411(6) . 2_655 ? #------------------------------------------------------------------------------ #------------------------------------------------------------------------------