# Electronic Supplementary Material (ESI) for Green Chemistry # This journal is © The Royal Society of Chemistry 2012 data_global #TrackingRef '- 3a.cif' _audit_update_record ; 2011-11-04 # Formatted by publCIF ; _journal_name_full 'Green Chemistry' _journal_coden_Cambridge 1048 loop_ _publ_author_name 'Liupan Yang' 'Daxin Shi' 'Shu Chen' 'Hongxin Chai' 'Danfei Huang' 'Qi Zhang' 'Jiarong Li' _publ_contact_author_name 'Jiarong Li' _publ_contact_author_email jrli@bit.edu.cn data_I _database_code_depnum_ccdc_archive 'CCDC 792400' _chemical_name_systematic ; Spiro[cyclopentane-1,2'(1'H)-pyrido[2,3-d]pyrimidin]- 4'(3'H)-one ; _chemical_name_common ? _chemical_formula_moiety 'C11 H13 N3 O' _chemical_formula_sum 'C11 H13 N3 O' _chemical_formula_iupac 'C11 H13 N3 O' _chemical_formula_weight 203.24 _chemical_melting_point ? _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P b c a' _symmetry_space_group_name_Hall '-P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, z' 'x, -y+1/2, z+1/2' '-x+1/2, -y, z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, -z' '-x, y-1/2, -z-1/2' 'x-1/2, y, -z-1/2' _cell_length_a 10.4000(10) _cell_length_b 12.1650(15) _cell_length_c 15.370(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1944.6(4) _cell_formula_units_Z 8 _cell_measurement_reflns_used 9441 _cell_measurement_theta_min 1.30 _cell_measurement_theta_max 35.60 _cell_measurement_temperature 113(2) _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.28 _exptl_crystal_density_diffrn 1.388 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 864 _exptl_absorpt_coefficient_mu 0.093 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(CrystalClear-SM Expert; Rigaku/MSC, 2009)' _exptl_absorpt_correction_T_min 0.9709 _exptl_absorpt_correction_T_max 0.9744 _exptl_special_details ; ; _diffrn_ambient_temperature 113(2) _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71075 _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator 'graphite multilayer' _diffrn_measurement_device_type 'Rigaku Saturn724 CCD' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 14.222 _diffrn_reflns_number 21571 _diffrn_reflns_av_R_equivalents 0.0365 _diffrn_reflns_av_sigmaI/netI 0.0190 _diffrn_reflns_theta_min 2.65 _diffrn_reflns_theta_max 27.88 _diffrn_reflns_theta_full 27.88 _diffrn_measured_fraction_theta_max 1.000 _diffrn_measured_fraction_theta_full 1.000 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _reflns_number_total 2314 _reflns_number_gt 2168 _reflns_threshold_expression I>2sigma(I) _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_R_factor_all 0.0427 _refine_ls_R_factor_gt 0.0395 _refine_ls_wR_factor_gt 0.0999 _refine_ls_wR_factor_ref 0.1026 _refine_ls_goodness_of_fit_ref 1.049 _refine_ls_restrained_S_all 1.049 _refine_ls_number_reflns 2314 _refine_ls_number_parameters 144 _refine_ls_number_restraints 0 _refine_ls_hydrogen_treatment mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0569P)^2^+0.6834P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_hydrogens difmap _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.404 _refine_diff_density_min -0.203 _refine_ls_extinction_method none _refine_ls_extinction_coef ? _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^ > \s(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. ; 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' N N 0.0061 0.0033 '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' _computing_data_collection 'Crystal Clear-SM Expert (Rigaku/MSC, 2009)' _computing_cell_refinement 'Crystal Clear-SM Expert (Rigaku/MSC, 2009)' _computing_data_reduction 'Crystal Clear-SM Expert (Rigaku/MSC, 2009)' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_molecular_graphics 'CrystalStructure (Rigaku/MSC, 2009)' _computing_publication_material 'CrystalStructure (Rigaku/MSC, 2009)' loop_ _atom_site_type_symbol _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_disorder_assembly _atom_site_disorder_group O O1 0.59391(7) 0.42006(6) 0.57792(5) 0.01563(19) Uani d . 1 2 . . N N1 0.94264(9) 0.63850(8) 0.68372(6) 0.0171(2) Uani d . 1 2 . . N N2 0.80796(9) 0.69549(8) 0.57226(6) 0.0155(2) Uani d . 1 2 . . N N3 0.64694(9) 0.58137(7) 0.51402(6) 0.0146(2) Uani d . 1 2 . . C C1 0.84778(10) 0.61467(9) 0.62723(7) 0.0137(2) Uani d . 1 2 . . C C2 0.78414(10) 0.51204(9) 0.62574(7) 0.0137(2) Uani d . 1 2 . . C C3 0.82323(11) 0.43170(9) 0.68436(7) 0.0164(2) Uani d . 1 2 . . H H3 0.7818 0.3621 0.6855 0.020 Uiso calc R 1 2 . . C C4 0.92347(11) 0.45420(9) 0.74123(7) 0.0185(2) Uani d . 1 2 . . H H4 0.9539 0.4001 0.7808 0.022 Uiso calc R 1 2 . . C C5 0.97766(11) 0.55837(9) 0.73836(7) 0.0184(2) Uani d . 1 2 . . H H5 1.0449 0.5740 0.7783 0.022 Uiso calc R 1 2 . . C C6 0.66943(10) 0.49939(9) 0.57020(7) 0.0130(2) Uani d . 1 2 . . C C7 0.74197(10) 0.66576(8) 0.49201(7) 0.0134(2) Uani d . 1 2 . . C C8 0.83702(11) 0.62728(9) 0.42121(7) 0.0168(2) Uani d . 1 2 . . H H8A 0.9065 0.5818 0.4465 0.020 Uiso calc R 1 2 . . H H8B 0.7924 0.5845 0.3755 0.020 Uiso calc R 1 2 . . C C9 0.88986(11) 0.73498(9) 0.38493(7) 0.0193(2) Uani d . 1 2 . . H H9A 0.9265 0.7242 0.3261 0.023 Uiso calc R 1 2 . . H H9B 0.9571 0.7656 0.4235 0.023 Uiso calc R 1 2 . . C C10 0.77185(12) 0.81065(10) 0.38176(8) 0.0231(3) Uani d . 1 2 . . H H10A 0.7316 0.8083 0.3234 0.028 Uiso calc R 1 2 . . H H10B 0.7969 0.8875 0.3947 0.028 Uiso calc R 1 2 . . C C11 0.67779(10) 0.76755(9) 0.45118(7) 0.0160(2) Uani d . 1 2 . . H H11A 0.5946 0.7474 0.4242 0.019 Uiso calc R 1 2 . . H H11B 0.6620 0.8244 0.4960 0.019 Uiso calc R 1 2 . . H H1 0.8471(15) 0.7598(14) 0.5750(10) 0.030(4) Uiso d . 1 2 . . H H2 0.5769(16) 0.5770(12) 0.4815(10) 0.024(4) Uiso d . 1 2 . . 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 O1 0.0148(4) 0.0129(4) 0.0193(4) -0.0014(3) 0.0001(3) 0.0009(3) N1 0.0166(4) 0.0201(5) 0.0147(4) -0.0014(4) -0.0011(3) -0.0010(4) N2 0.0177(5) 0.0121(5) 0.0166(4) -0.0029(4) -0.0033(4) 0.0003(3) N3 0.0123(4) 0.0140(4) 0.0175(4) -0.0023(3) -0.0029(4) 0.0020(3) C1 0.0134(5) 0.0147(5) 0.0131(5) 0.0007(4) 0.0024(4) -0.0013(4) C2 0.0135(5) 0.0146(5) 0.0130(5) 0.0008(4) 0.0008(4) -0.0010(4) C3 0.0185(5) 0.0146(5) 0.0161(5) 0.0016(4) 0.0010(4) -0.0001(4) C4 0.0201(5) 0.0205(5) 0.0147(5) 0.0049(4) -0.0008(4) 0.0019(4) C5 0.0162(5) 0.0249(6) 0.0142(5) 0.0009(4) -0.0018(4) -0.0007(4) C6 0.0130(5) 0.0121(5) 0.0139(5) 0.0016(4) 0.0021(4) -0.0016(4) C7 0.0129(5) 0.0122(5) 0.0152(5) -0.0014(4) -0.0008(4) 0.0011(4) C8 0.0179(5) 0.0153(5) 0.0171(5) 0.0017(4) 0.0006(4) 0.0003(4) C9 0.0182(5) 0.0191(6) 0.0206(5) 0.0000(4) 0.0036(4) 0.0028(4) C10 0.0252(6) 0.0196(6) 0.0246(6) 0.0040(5) 0.0057(5) 0.0082(5) C11 0.0147(5) 0.0138(5) 0.0195(5) 0.0010(4) -0.0011(4) 0.0030(4) _geom_special_details ; All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag O1 C6 . 1.2500(13) ? N1 C5 . 1.3372(14) ? N1 C1 . 1.3458(14) ? N2 C1 . 1.3609(14) ? N2 C7 . 1.4571(13) ? N2 H1 . 0.882(17) ? N3 C6 . 1.3397(14) ? N3 C7 . 1.4646(13) ? N3 H2 . 0.885(16) ? C1 C2 . 1.4132(15) ? C2 C3 . 1.3900(15) ? C2 C6 . 1.4750(14) ? C3 C4 . 1.3878(16) ? C3 H3 . 0.9500 ? C4 C5 . 1.3876(16) ? C4 H4 . 0.9500 ? C5 H5 . 0.9500 ? C7 C11 . 1.5404(14) ? C7 C8 . 1.5428(15) ? C8 C9 . 1.5262(16) ? C8 H8A . 0.9900 ? C8 H8B . 0.9900 ? C9 C10 . 1.5349(16) ? C9 H9A . 0.9900 ? C9 H9B . 0.9900 ? C10 C11 . 1.5397(15) ? C10 H10A . 0.9900 ? C10 H10B . 0.9900 ? C11 H11A . 0.9900 ? C11 H11B . 0.9900 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C5 N1 C1 . . 116.60(10) ? C1 N2 C7 . . 119.32(9) ? C1 N2 H1 . . 118.1(10) ? C7 N2 H1 . . 118.5(10) ? C6 N3 C7 . . 123.56(9) ? C6 N3 H2 . . 117.6(9) ? C7 N3 H2 . . 117.8(9) ? N1 C1 N2 . . 117.90(10) ? N1 C1 C2 . . 122.96(10) ? N2 C1 C2 . . 119.05(10) ? C3 C2 C1 . . 118.28(10) ? C3 C2 C6 . . 122.57(10) ? C1 C2 C6 . . 118.70(9) ? C4 C3 C2 . . 119.29(10) ? C4 C3 H3 . . 120.4 ? C2 C3 H3 . . 120.4 ? C5 C4 C3 . . 117.72(10) ? C5 C4 H4 . . 121.1 ? C3 C4 H4 . . 121.1 ? N1 C5 C4 . . 125.11(10) ? N1 C5 H5 . . 117.4 ? C4 C5 H5 . . 117.4 ? O1 C6 N3 . . 121.75(10) ? O1 C6 C2 . . 122.26(10) ? N3 C6 C2 . . 115.89(9) ? N2 C7 N3 . . 107.23(8) ? N2 C7 C11 . . 110.45(9) ? N3 C7 C11 . . 111.42(9) ? N2 C7 C8 . . 111.75(9) ? N3 C7 C8 . . 112.50(9) ? C11 C7 C8 . . 103.55(8) ? C9 C8 C7 . . 103.17(9) ? C9 C8 H8A . . 111.1 ? C7 C8 H8A . . 111.1 ? C9 C8 H8B . . 111.1 ? C7 C8 H8B . . 111.1 ? H8A C8 H8B . . 109.1 ? C8 C9 C10 . . 103.80(9) ? C8 C9 H9A . . 111.0 ? C10 C9 H9A . . 111.0 ? C8 C9 H9B . . 111.0 ? C10 C9 H9B . . 111.0 ? H9A C9 H9B . . 109.0 ? C9 C10 C11 . . 106.36(9) ? C9 C10 H10A . . 110.5 ? C11 C10 H10A . . 110.5 ? C9 C10 H10B . . 110.5 ? C11 C10 H10B . . 110.5 ? H10A C10 H10B . . 108.6 ? C10 C11 C7 . . 106.30(9) ? C10 C11 H11A . . 110.5 ? C7 C11 H11A . . 110.5 ? C10 C11 H11B . . 110.5 ? C7 C11 H11B . . 110.5 ? H11A C11 H11B . . 108.7 ? 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag C5 N1 C1 N2 . . . . 178.43(10) ? C5 N1 C1 C2 . . . . 1.72(16) ? C7 N2 C1 N1 . . . . 158.25(10) ? C7 N2 C1 C2 . . . . -24.91(15) ? N1 C1 C2 C3 . . . . -1.20(16) ? N2 C1 C2 C3 . . . . -177.86(10) ? N1 C1 C2 C6 . . . . 171.29(10) ? N2 C1 C2 C6 . . . . -5.38(15) ? C1 C2 C3 C4 . . . . -0.71(16) ? C6 C2 C3 C4 . . . . -172.89(10) ? C2 C3 C4 C5 . . . . 1.92(16) ? C1 N1 C5 C4 . . . . -0.39(17) ? C3 C4 C5 N1 . . . . -1.43(17) ? C7 N3 C6 O1 . . . . -169.27(9) ? C7 N3 C6 C2 . . . . 14.28(15) ? C3 C2 C6 O1 . . . . 6.53(16) ? C1 C2 C6 O1 . . . . -165.62(10) ? C3 C2 C6 N3 . . . . -177.04(10) ? C1 C2 C6 N3 . . . . 10.81(14) ? C1 N2 C7 N3 . . . . 44.94(13) ? C1 N2 C7 C11 . . . . 166.52(9) ? C1 N2 C7 C8 . . . . -78.77(12) ? C6 N3 C7 N2 . . . . -40.32(13) ? C6 N3 C7 C11 . . . . -161.29(10) ? C6 N3 C7 C8 . . . . 82.94(12) ? N2 C7 C8 C9 . . . . -79.95(10) ? N3 C7 C8 C9 . . . . 159.36(9) ? C11 C7 C8 C9 . . . . 38.94(10) ? C7 C8 C9 C10 . . . . -39.83(11) ? C8 C9 C10 C11 . . . . 25.43(12) ? C9 C10 C11 C7 . . . . -1.25(12) ? N2 C7 C11 C10 . . . . 96.69(10) ? N3 C7 C11 C10 . . . . -144.24(9) ? C8 C7 C11 C10 . . . . -23.09(11) ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA N2 H1 O1 2_655 0.88(2) 2.05(2) 2.9180(10) 170(2) N3 H2 O1 5_666 0.89(2) 2.00(2) 2.8760(10) 172.0(10) # Attachment '- 4b.cif' # Electronic Supplementary Material (ESI) for Green Chemistry # This journal is ?The Royal Society of Chemistry 2011 # Attachment '- 4b.cif' data_bo1423 _database_code_depnum_ccdc_archive 'CCDC 854865' #TrackingRef '- 4b.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H14 Br N3 O' _chemical_formula_weight 296.17 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' N N 0.0061 0.0033 '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' Br Br -0.2901 2.4595 '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 10.591(3) _cell_length_b 12.359(3) _cell_length_c 9.116(3) _cell_angle_alpha 90.00 _cell_angle_beta 97.951(4) _cell_angle_gamma 90.00 _cell_volume 1181.7(6) _cell_formula_units_Z 4 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used 3621 _cell_measurement_theta_min 2.547 _cell_measurement_theta_max 29.122 _exptl_crystal_description Platelet _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.665 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 600 _exptl_absorpt_coefficient_mu 3.465 _exptl_absorpt_correction_type Multi-scans _exptl_absorpt_correction_T_min 0.3350 _exptl_absorpt_correction_T_max 0.7572 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 153(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Rotating Anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type AFC10/Saturn724+ _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 28.5714 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 10128 _diffrn_reflns_av_R_equivalents 0.0458 _diffrn_reflns_av_sigmaI/netI 0.0513 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.55 _diffrn_reflns_theta_max 29.10 _reflns_number_total 3160 _reflns_number_gt 2283 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Inc., 2008)' _computing_cell_refinement 'CrystalClear (Rigaku Inc., 2008)' _computing_data_reduction 'CrystalClear (Rigaku Inc., 2008)' _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^)+(0.0295P)^2^+0.1260P] 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_number_reflns 3160 _refine_ls_number_parameters 162 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0555 _refine_ls_R_factor_gt 0.0345 _refine_ls_wR_factor_ref 0.0739 _refine_ls_wR_factor_gt 0.0685 _refine_ls_goodness_of_fit_ref 0.999 _refine_ls_restrained_S_all 0.999 _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 Br1 Br 0.99820(2) 0.65490(2) 0.61599(3) 0.03640(10) Uani 1 1 d . . . O1 O 0.58435(14) 0.40734(11) 0.39085(16) 0.0171(3) Uani 1 1 d . . . N1 N 0.45035(17) 0.52063(14) 0.2500(2) 0.0151(4) Uani 1 1 d . . . N2 N 0.49356(17) 0.71034(14) 0.2458(2) 0.0188(4) Uani 1 1 d . . . N3 N 0.68151(16) 0.78374(13) 0.3597(2) 0.0176(4) Uani 1 1 d . . . C1 C 0.2735(2) 0.64979(16) 0.2411(2) 0.0150(4) Uani 1 1 d . . . H1A H 0.2814 0.6418 0.3501 0.018 Uiso 1 1 calc R . . H1B H 0.2496 0.7257 0.2164 0.018 Uiso 1 1 calc R . . C2 C 0.1676(2) 0.57477(17) 0.1687(2) 0.0179(5) Uani 1 1 d . . . H2A H 0.1865 0.4994 0.2015 0.021 Uiso 1 1 calc R . . H2B H 0.0855 0.5960 0.2005 0.021 Uiso 1 1 calc R . . C3 C 0.1565(2) 0.58081(18) -0.0002(2) 0.0194(5) Uani 1 1 d . . . H3A H 0.0902 0.5296 -0.0448 0.023 Uiso 1 1 calc R . . H3B H 0.1303 0.6547 -0.0336 0.023 Uiso 1 1 calc R . . C4 C 0.2831(2) 0.55308(17) -0.0524(2) 0.0172(5) Uani 1 1 d . . . H4A H 0.2751 0.5617 -0.1613 0.021 Uiso 1 1 calc R . . H4B H 0.3046 0.4765 -0.0285 0.021 Uiso 1 1 calc R . . C5 C 0.3902(2) 0.62565(16) 0.0209(2) 0.0160(4) Uani 1 1 d . . . H5A H 0.3743 0.7006 -0.0152 0.019 Uiso 1 1 calc R . . H5B H 0.4717 0.6014 -0.0098 0.019 Uiso 1 1 calc R . . C6 C 0.40340(19) 0.62564(15) 0.1905(2) 0.0129(4) Uani 1 1 d . . . C7 C 0.55747(19) 0.49967(15) 0.3433(2) 0.0127(4) Uani 1 1 d . . . C8 C 0.64262(19) 0.59204(16) 0.3832(2) 0.0125(4) Uani 1 1 d . . . C9 C 0.6063(2) 0.69577(16) 0.3293(2) 0.0139(4) Uani 1 1 d . . . C10 C 0.7594(2) 0.57798(17) 0.4683(2) 0.0174(5) Uani 1 1 d . . . H10 H 0.7863 0.5086 0.5051 0.021 Uiso 1 1 calc R . . C11 C 0.8365(2) 0.66793(17) 0.4987(3) 0.0203(5) Uani 1 1 d . . . C12 C 0.7942(2) 0.76778(17) 0.4435(3) 0.0203(5) Uani 1 1 d . . . H12 H 0.8482 0.8286 0.4665 0.024 Uiso 1 1 calc R . . H1N H 0.408(2) 0.4668(17) 0.220(2) 0.015(6) Uiso 1 1 d . . . H2N H 0.474(2) 0.7700(19) 0.208(3) 0.026(7) 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 Br1 0.02057(13) 0.02781(14) 0.05373(19) 0.01191(13) -0.01997(11) -0.00860(11) O1 0.0199(8) 0.0096(7) 0.0194(8) 0.0021(6) -0.0054(6) 0.0000(6) N1 0.0143(9) 0.0080(8) 0.0209(10) -0.0002(7) -0.0049(7) -0.0027(7) N2 0.0163(10) 0.0070(9) 0.0298(11) 0.0047(8) -0.0085(8) -0.0006(7) N3 0.0143(10) 0.0111(9) 0.0259(11) 0.0016(8) -0.0027(8) -0.0045(7) C1 0.0165(11) 0.0128(10) 0.0153(10) -0.0012(8) 0.0011(8) 0.0017(9) C2 0.0133(11) 0.0189(11) 0.0216(12) -0.0022(9) 0.0031(9) -0.0025(9) C3 0.0130(11) 0.0208(11) 0.0227(12) -0.0027(10) -0.0029(9) -0.0036(9) C4 0.0194(11) 0.0184(10) 0.0131(10) -0.0017(9) -0.0003(8) 0.0000(9) C5 0.0167(11) 0.0145(10) 0.0175(11) 0.0026(9) 0.0050(9) 0.0032(8) C6 0.0117(10) 0.0070(9) 0.0182(11) 0.0004(8) -0.0042(8) 0.0004(8) C7 0.0135(10) 0.0112(10) 0.0132(10) -0.0005(8) 0.0013(8) 0.0009(8) C8 0.0129(10) 0.0113(10) 0.0130(10) -0.0005(8) 0.0006(8) -0.0002(8) C9 0.0137(10) 0.0111(9) 0.0165(11) -0.0003(8) 0.0010(8) -0.0006(8) C10 0.0153(11) 0.0151(10) 0.0204(11) 0.0041(9) -0.0020(9) -0.0008(9) C11 0.0120(10) 0.0200(11) 0.0262(12) 0.0027(10) -0.0064(9) -0.0040(9) C12 0.0161(11) 0.0148(10) 0.0281(13) -0.0019(10) -0.0034(9) -0.0052(9) _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 Br1 C11 1.896(2) . ? O1 C7 1.240(2) . ? N1 C7 1.346(2) . ? N1 C6 1.467(2) . ? N1 H1N 0.83(2) . ? N2 C9 1.336(3) . ? N2 C6 1.459(3) . ? N2 H2N 0.83(2) . ? N3 C12 1.339(3) . ? N3 C9 1.354(3) . ? C1 C2 1.533(3) . ? C1 C6 1.539(3) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C2 C3 1.530(3) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.523(3) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 C5 1.525(3) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C6 1.533(3) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C7 C8 1.469(3) . ? C8 C10 1.377(3) . ? C8 C9 1.407(3) . ? C10 C11 1.384(3) . ? C10 H10 0.9500 . ? C11 C12 1.384(3) . ? C12 H12 0.9500 . ? 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 C7 N1 C6 128.11(17) . . ? C7 N1 H1N 115.1(15) . . ? C6 N1 H1N 116.7(15) . . ? C9 N2 C6 126.21(17) . . ? C9 N2 H2N 120.3(17) . . ? C6 N2 H2N 112.6(17) . . ? C12 N3 C9 116.82(17) . . ? C2 C1 C6 112.62(16) . . ? C2 C1 H1A 109.1 . . ? C6 C1 H1A 109.1 . . ? C2 C1 H1B 109.1 . . ? C6 C1 H1B 109.1 . . ? H1A C1 H1B 107.8 . . ? C3 C2 C1 110.73(17) . . ? C3 C2 H2A 109.5 . . ? C1 C2 H2A 109.5 . . ? C3 C2 H2B 109.5 . . ? C1 C2 H2B 109.5 . . ? H2A C2 H2B 108.1 . . ? C4 C3 C2 110.80(17) . . ? C4 C3 H3A 109.5 . . ? C2 C3 H3A 109.5 . . ? C4 C3 H3B 109.5 . . ? C2 C3 H3B 109.5 . . ? H3A C3 H3B 108.1 . . ? C3 C4 C5 111.35(17) . . ? C3 C4 H4A 109.4 . . ? C5 C4 H4A 109.4 . . ? C3 C4 H4B 109.4 . . ? C5 C4 H4B 109.4 . . ? H4A C4 H4B 108.0 . . ? C4 C5 C6 113.60(18) . . ? C4 C5 H5A 108.8 . . ? C6 C5 H5A 108.8 . . ? C4 C5 H5B 108.8 . . ? C6 C5 H5B 108.8 . . ? H5A C5 H5B 107.7 . . ? N2 C6 N1 109.55(16) . . ? N2 C6 C5 108.24(17) . . ? N1 C6 C5 110.62(17) . . ? N2 C6 C1 109.04(16) . . ? N1 C6 C1 109.38(17) . . ? C5 C6 C1 109.98(16) . . ? O1 C7 N1 122.07(18) . . ? O1 C7 C8 121.69(18) . . ? N1 C7 C8 116.22(17) . . ? C10 C8 C9 119.49(18) . . ? C10 C8 C7 120.94(18) . . ? C9 C8 C7 119.53(18) . . ? N2 C9 N3 117.56(18) . . ? N2 C9 C8 120.06(18) . . ? N3 C9 C8 122.37(18) . . ? C8 C10 C11 118.05(19) . . ? C8 C10 H10 121.0 . . ? C11 C10 H10 121.0 . . ? C12 C11 C10 119.4(2) . . ? C12 C11 Br1 120.17(16) . . ? C10 C11 Br1 120.42(16) . . ? N3 C12 C11 123.84(19) . . ? N3 C12 H12 118.1 . . ? C11 C12 H12 118.1 . . ? 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 -56.1(2) . . . . ? C1 C2 C3 C4 56.8(2) . . . . ? C2 C3 C4 C5 -55.7(2) . . . . ? C3 C4 C5 C6 54.2(2) . . . . ? C9 N2 C6 N1 4.4(3) . . . . ? C9 N2 C6 C5 -116.3(2) . . . . ? C9 N2 C6 C1 124.1(2) . . . . ? C7 N1 C6 N2 1.1(3) . . . . ? C7 N1 C6 C5 120.3(2) . . . . ? C7 N1 C6 C1 -118.4(2) . . . . ? C4 C5 C6 N2 -170.86(16) . . . . ? C4 C5 C6 N1 69.1(2) . . . . ? C4 C5 C6 C1 -51.8(2) . . . . ? C2 C1 C6 N2 171.29(17) . . . . ? C2 C1 C6 N1 -68.9(2) . . . . ? C2 C1 C6 C5 52.7(2) . . . . ? C6 N1 C7 O1 176.9(2) . . . . ? C6 N1 C7 C8 -4.5(3) . . . . ? O1 C7 C8 C10 3.8(3) . . . . ? N1 C7 C8 C10 -174.77(19) . . . . ? O1 C7 C8 C9 -178.41(19) . . . . ? N1 C7 C8 C9 3.0(3) . . . . ? C6 N2 C9 N3 174.7(2) . . . . ? C6 N2 C9 C8 -5.9(3) . . . . ? C12 N3 C9 N2 180.0(2) . . . . ? C12 N3 C9 C8 0.6(3) . . . . ? C10 C8 C9 N2 179.6(2) . . . . ? C7 C8 C9 N2 1.8(3) . . . . ? C10 C8 C9 N3 -1.0(3) . . . . ? C7 C8 C9 N3 -178.8(2) . . . . ? C9 C8 C10 C11 0.6(3) . . . . ? C7 C8 C10 C11 178.3(2) . . . . ? C8 C10 C11 C12 0.2(3) . . . . ? C8 C10 C11 Br1 179.67(16) . . . . ? C9 N3 C12 C11 0.3(3) . . . . ? C10 C11 C12 N3 -0.6(4) . . . . ? Br1 C11 C12 N3 179.88(18) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 29.10 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.545 _refine_diff_density_min -0.664 _refine_diff_density_rms 0.081 # Attachment '- 4e.cif' # Electronic Supplementary Material (ESI) for Green Chemistry # This journal is ?The Royal Society of Chemistry 2011 # Attachment '- 4e.cif' data_bo1428 _database_code_depnum_ccdc_archive 'CCDC 854866' #TrackingRef '- 4e.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C23 H28 Cl N3 O2' _chemical_formula_weight 413.93 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' N N 0.0061 0.0033 '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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.355(2) _cell_length_b 10.746(3) _cell_length_c 12.843(4) _cell_angle_alpha 98.611(2) _cell_angle_beta 99.924(3) _cell_angle_gamma 110.707(3) _cell_volume 1034.3(5) _cell_formula_units_Z 2 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used 3355 _cell_measurement_theta_min 2.683 _cell_measurement_theta_max 29.120 _exptl_crystal_description Block _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.33 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.329 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 440 _exptl_absorpt_coefficient_mu 0.210 _exptl_absorpt_correction_type Multi-scans _exptl_absorpt_correction_T_min 0.9346 _exptl_absorpt_correction_T_max 0.9796 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 153(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Rotating Anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type AFC10/Saturn724+ _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 28.5714 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 11424 _diffrn_reflns_av_R_equivalents 0.0299 _diffrn_reflns_av_sigmaI/netI 0.0481 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.34 _diffrn_reflns_theta_max 29.14 _reflns_number_total 5406 _reflns_number_gt 4046 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Inc., 2008)' _computing_cell_refinement 'CrystalClear (Rigaku Inc., 2008)' _computing_data_reduction 'CrystalClear (Rigaku Inc., 2008)' _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^)+(0.0536P)^2^+0.2960P] 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_number_reflns 5406 _refine_ls_number_parameters 272 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0662 _refine_ls_R_factor_gt 0.0464 _refine_ls_wR_factor_ref 0.1160 _refine_ls_wR_factor_gt 0.1083 _refine_ls_goodness_of_fit_ref 1.001 _refine_ls_restrained_S_all 1.001 _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 Cl1 Cl 0.47155(5) 0.94837(4) 0.86693(3) 0.02674(12) Uani 1 1 d . . . O1 O 0.79191(15) 0.90076(13) 0.52609(9) 0.0309(3) Uani 1 1 d . . . O2 O 0.31427(19) 0.50545(13) 0.98262(10) 0.0347(3) Uani 1 1 d . . . H2 H 0.3669 0.5054 1.0446 0.042 Uiso 1 1 calc R . . N1 N 0.44526(16) 0.53913(13) 0.21298(10) 0.0172(3) Uani 1 1 d . . . N2 N 0.74050(17) 0.66897(14) 0.23332(11) 0.0203(3) Uani 1 1 d . . . N3 N 0.90071(18) 0.85539(15) 0.38323(11) 0.0263(3) Uani 1 1 d . . . C1 C 0.30338(19) 0.50079(15) 0.25546(12) 0.0164(3) Uani 1 1 d . . . C2 C 0.1437(2) 0.38199(17) 0.18348(13) 0.0221(3) Uani 1 1 d . . . H2A H 0.1830 0.3164 0.1437 0.051 Uiso 1 1 calc R . . H2B H 0.0807 0.4159 0.1292 0.051 Uiso 1 1 calc R . . C3 C 0.0171(2) 0.30833(18) 0.24700(14) 0.0277(4) Uani 1 1 d . . . H3A H -0.0929 0.2406 0.1961 0.064 Uiso 1 1 calc R . . H3B H 0.0712 0.2590 0.2913 0.064 Uiso 1 1 calc R . . C4 C -0.0250(2) 0.41052(19) 0.32024(14) 0.0288(4) Uani 1 1 d . . . H4A H -0.1146 0.3615 0.3571 0.066 Uiso 1 1 calc R . . H4B H -0.0748 0.4622 0.2760 0.066 Uiso 1 1 calc R . . C5 C 0.1414(2) 0.50988(17) 0.40530(13) 0.0221(3) Uani 1 1 d . . . H5A H 0.1176 0.5879 0.4403 0.051 Uiso 1 1 calc R . . H5B H 0.1698 0.4628 0.4622 0.051 Uiso 1 1 calc R . . C6 C 0.30015(19) 0.56401(15) 0.35775(12) 0.0158(3) Uani 1 1 d . . . C7 C 0.45316(19) 0.67574(15) 0.41848(11) 0.0146(3) Uani 1 1 d . . . C8 C 0.60154(19) 0.71667(15) 0.37576(11) 0.0162(3) Uani 1 1 d . . . C9 C 0.59371(19) 0.64248(15) 0.27332(12) 0.0159(3) Uani 1 1 d . . . C10 C 0.7697(2) 0.83111(16) 0.43461(12) 0.0206(3) Uani 1 1 d . . . C11 C 0.88819(19) 0.80214(15) 0.26948(12) 0.0175(3) Uani 1 1 d . . . C12 C 1.0627(2) 0.78831(17) 0.26423(13) 0.0225(3) Uani 1 1 d . . . H12A H 1.1610 0.8748 0.3051 0.052 Uiso 1 1 calc R . . H12B H 1.0714 0.7151 0.3006 0.052 Uiso 1 1 calc R . . C13 C 1.0842(2) 0.75558(19) 0.14924(14) 0.0300(4) Uani 1 1 d . . . H13A H 1.2038 0.7565 0.1521 0.069 Uiso 1 1 calc R . . H13B H 0.9973 0.6629 0.1109 0.069 Uiso 1 1 calc R . . C14 C 1.0572(2) 0.8594(2) 0.08717(15) 0.0355(5) Uani 1 1 d . . . H14A H 1.1508 0.9508 0.1217 0.082 Uiso 1 1 calc R . . H14B H 1.0660 0.8341 0.0116 0.082 Uiso 1 1 calc R . . C15 C 0.8780(3) 0.8646(2) 0.08627(15) 0.0330(4) Uani 1 1 d . . . H15A H 0.7843 0.7746 0.0480 0.076 Uiso 1 1 calc R . . H15B H 0.8631 0.9335 0.0465 0.076 Uiso 1 1 calc R . . C16 C 0.8598(2) 0.90153(18) 0.20187(15) 0.0276(4) Uani 1 1 d . . . H16A H 0.7406 0.9014 0.1992 0.064 Uiso 1 1 calc R . . H16B H 0.9470 0.9950 0.2376 0.064 Uiso 1 1 calc R . . C17 C 0.45493(18) 0.74436(15) 0.52921(12) 0.0158(3) Uani 1 1 d . . . C18 C 0.3998(2) 0.85132(16) 0.54471(13) 0.0213(3) Uani 1 1 d . . . H18 H 0.3580 0.8816 0.4838 0.026 Uiso 1 1 calc R . . C19 C 0.4050(2) 0.91522(17) 0.64851(13) 0.0232(3) Uani 1 1 d . . . H19 H 0.3686 0.9896 0.6589 0.028 Uiso 1 1 calc R . . C20 C 0.4638(2) 0.86884(16) 0.73632(12) 0.0185(3) Uani 1 1 d . . . C21 C 0.5142(2) 0.75973(18) 0.72245(13) 0.0235(3) Uani 1 1 d . . . H21 H 0.5521 0.7276 0.7833 0.028 Uiso 1 1 calc R . . C22 C 0.5089(2) 0.69730(17) 0.61844(13) 0.0215(3) Uani 1 1 d . . . H22 H 0.5426 0.6215 0.6082 0.026 Uiso 1 1 calc R . . C23 C 0.3592(3) 0.6407(2) 0.97101(16) 0.0354(4) Uani 1 1 d . . . H23A H 0.3591 0.6981 1.0379 0.042 Uiso 1 1 calc R . . H23B H 0.2729 0.6434 0.9101 0.042 Uiso 1 1 calc R . . H23C H 0.4769 0.6748 0.9570 0.042 Uiso 1 1 calc R . . H3N H 0.996(3) 0.926(2) 0.4156(17) 0.037(6) Uiso 1 1 d . . . H2N H 0.723(3) 0.621(2) 0.1703(18) 0.037(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 Cl1 0.0278(2) 0.0350(2) 0.01447(18) -0.00310(16) 0.00581(14) 0.01207(18) O1 0.0215(6) 0.0325(7) 0.0195(6) -0.0107(5) 0.0082(5) -0.0067(5) O2 0.0462(8) 0.0288(7) 0.0160(6) 0.0007(5) 0.0045(5) 0.0024(6) N1 0.0160(6) 0.0174(6) 0.0131(6) -0.0001(5) 0.0027(5) 0.0024(5) N2 0.0172(6) 0.0201(7) 0.0155(6) -0.0041(5) 0.0071(5) -0.0005(5) N3 0.0175(7) 0.0280(8) 0.0174(7) -0.0082(6) 0.0068(5) -0.0056(6) C1 0.0145(7) 0.0161(7) 0.0149(7) 0.0020(6) 0.0024(5) 0.0027(6) C2 0.0159(7) 0.0225(8) 0.0179(7) -0.0028(6) 0.0026(6) -0.0007(6) C3 0.0208(8) 0.0230(9) 0.0267(9) -0.0027(7) 0.0062(6) -0.0031(7) C4 0.0169(8) 0.0318(10) 0.0272(9) -0.0013(7) 0.0077(6) -0.0007(7) C5 0.0170(7) 0.0231(8) 0.0192(8) 0.0002(6) 0.0073(6) 0.0002(6) C6 0.0151(7) 0.0156(7) 0.0146(7) 0.0030(6) 0.0041(5) 0.0036(6) C7 0.0163(7) 0.0142(7) 0.0119(6) 0.0020(5) 0.0036(5) 0.0048(6) C8 0.0145(7) 0.0165(7) 0.0127(7) 0.0005(5) 0.0027(5) 0.0019(6) C9 0.0154(7) 0.0155(7) 0.0145(7) 0.0020(6) 0.0043(5) 0.0034(6) C10 0.0166(7) 0.0204(8) 0.0170(7) -0.0012(6) 0.0047(6) 0.0001(6) C11 0.0146(7) 0.0178(8) 0.0147(7) -0.0020(6) 0.0050(5) 0.0015(6) C12 0.0158(7) 0.0264(9) 0.0226(8) 0.0017(7) 0.0049(6) 0.0066(6) C13 0.0192(8) 0.0363(10) 0.0286(9) -0.0055(8) 0.0106(7) 0.0068(7) C14 0.0298(9) 0.0410(11) 0.0209(9) 0.0027(8) 0.0111(7) -0.0041(8) C15 0.0352(10) 0.0321(10) 0.0262(9) 0.0132(8) 0.0044(7) 0.0054(8) C16 0.0294(9) 0.0218(8) 0.0309(9) 0.0041(7) 0.0067(7) 0.0100(7) C17 0.0132(6) 0.0162(7) 0.0143(7) 0.0013(6) 0.0050(5) 0.0014(6) C18 0.0266(8) 0.0219(8) 0.0159(7) 0.0037(6) 0.0049(6) 0.0104(7) C19 0.0286(8) 0.0232(8) 0.0197(8) 0.0017(6) 0.0066(6) 0.0133(7) C20 0.0171(7) 0.0217(8) 0.0124(7) -0.0016(6) 0.0049(5) 0.0043(6) C21 0.0286(8) 0.0316(9) 0.0141(7) 0.0063(6) 0.0058(6) 0.0153(7) C22 0.0280(8) 0.0232(8) 0.0190(7) 0.0051(6) 0.0075(6) 0.0156(7) C23 0.0419(11) 0.0360(11) 0.0300(10) 0.0065(8) 0.0069(8) 0.0185(9) _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 Cl1 C20 1.7442(16) . ? O1 C10 1.2401(19) . ? O2 C23 1.405(2) . ? O2 H2 0.8400 . ? N1 C9 1.3450(18) . ? N1 C1 1.3481(19) . ? N2 C9 1.365(2) . ? N2 C11 1.4631(19) . ? N2 H2N 0.85(2) . ? N3 C10 1.342(2) . ? N3 C11 1.4585(19) . ? N3 H3N 0.86(2) . ? C1 C6 1.395(2) . ? C1 C2 1.511(2) . ? C2 C3 1.519(2) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.514(2) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 C5 1.531(2) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C6 1.520(2) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 C7 1.4052(19) . ? C7 C8 1.397(2) . ? C7 C17 1.496(2) . ? C8 C9 1.411(2) . ? C8 C10 1.480(2) . ? C11 C12 1.528(2) . ? C11 C16 1.529(2) . ? C12 C13 1.523(2) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 C14 1.521(3) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 C15 1.516(3) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 C16 1.526(3) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C17 C18 1.382(2) . ? C17 C22 1.389(2) . ? C18 C19 1.391(2) . ? C18 H18 0.9500 . ? C19 C20 1.383(2) . ? C19 H19 0.9500 . ? C20 C21 1.377(2) . ? C21 C22 1.388(2) . ? C21 H21 0.9500 . ? C22 H22 0.9500 . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? 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 C23 O2 H2 109.5 . . ? C9 N1 C1 118.31(13) . . ? C9 N2 C11 121.34(13) . . ? C9 N2 H2N 114.5(14) . . ? C11 N2 H2N 119.1(14) . . ? C10 N3 C11 127.65(13) . . ? C10 N3 H3N 115.6(14) . . ? C11 N3 H3N 114.6(14) . . ? N1 C1 C6 123.80(13) . . ? N1 C1 C2 114.91(13) . . ? C6 C1 C2 121.29(13) . . ? C1 C2 C3 112.60(13) . . ? C1 C2 H2A 109.1 . . ? C3 C2 H2A 109.1 . . ? C1 C2 H2B 109.1 . . ? C3 C2 H2B 109.1 . . ? H2A C2 H2B 107.8 . . ? C4 C3 C2 109.83(15) . . ? C4 C3 H3A 109.7 . . ? C2 C3 H3A 109.7 . . ? C4 C3 H3B 109.7 . . ? C2 C3 H3B 109.7 . . ? H3A C3 H3B 108.2 . . ? C3 C4 C5 110.56(14) . . ? C3 C4 H4A 109.5 . . ? C5 C4 H4A 109.5 . . ? C3 C4 H4B 109.5 . . ? C5 C4 H4B 109.5 . . ? H4A C4 H4B 108.1 . . ? C6 C5 C4 113.04(13) . . ? C6 C5 H5A 109.0 . . ? C4 C5 H5A 109.0 . . ? C6 C5 H5B 109.0 . . ? C4 C5 H5B 109.0 . . ? H5A C5 H5B 107.8 . . ? C1 C6 C7 117.62(13) . . ? C1 C6 C5 121.61(13) . . ? C7 C6 C5 120.68(13) . . ? C8 C7 C6 119.31(13) . . ? C8 C7 C17 121.71(12) . . ? C6 C7 C17 118.93(13) . . ? C7 C8 C9 118.67(13) . . ? C7 C8 C10 123.20(13) . . ? C9 C8 C10 118.08(13) . . ? N1 C9 N2 116.92(13) . . ? N1 C9 C8 122.15(13) . . ? N2 C9 C8 120.87(13) . . ? O1 C10 N3 120.94(14) . . ? O1 C10 C8 123.29(14) . . ? N3 C10 C8 115.76(14) . . ? N3 C11 N2 107.79(12) . . ? N3 C11 C12 106.90(13) . . ? N2 C11 C12 111.08(13) . . ? N3 C11 C16 109.86(14) . . ? N2 C11 C16 111.01(13) . . ? C12 C11 C16 110.08(13) . . ? C13 C12 C11 113.88(13) . . ? C13 C12 H12A 108.8 . . ? C11 C12 H12A 108.8 . . ? C13 C12 H12B 108.8 . . ? C11 C12 H12B 108.8 . . ? H12A C12 H12B 107.7 . . ? C14 C13 C12 110.65(15) . . ? C14 C13 H13A 109.5 . . ? C12 C13 H13A 109.5 . . ? C14 C13 H13B 109.5 . . ? C12 C13 H13B 109.5 . . ? H13A C13 H13B 108.1 . . ? C15 C14 C13 110.50(14) . . ? C15 C14 H14A 109.6 . . ? C13 C14 H14A 109.6 . . ? C15 C14 H14B 109.6 . . ? C13 C14 H14B 109.6 . . ? H14A C14 H14B 108.1 . . ? C14 C15 C16 110.67(15) . . ? C14 C15 H15A 109.5 . . ? C16 C15 H15A 109.5 . . ? C14 C15 H15B 109.5 . . ? C16 C15 H15B 109.5 . . ? H15A C15 H15B 108.1 . . ? C15 C16 C11 112.35(15) . . ? C15 C16 H16A 109.1 . . ? C11 C16 H16A 109.1 . . ? C15 C16 H16B 109.1 . . ? C11 C16 H16B 109.1 . . ? H16A C16 H16B 107.9 . . ? C18 C17 C22 119.09(14) . . ? C18 C17 C7 121.61(13) . . ? C22 C17 C7 119.28(14) . . ? C17 C18 C19 120.77(15) . . ? C17 C18 H18 119.6 . . ? C19 C18 H18 119.6 . . ? C20 C19 C18 119.00(15) . . ? C20 C19 H19 120.5 . . ? C18 C19 H19 120.5 . . ? C21 C20 C19 121.20(14) . . ? C21 C20 Cl1 119.33(12) . . ? C19 C20 Cl1 119.47(13) . . ? C20 C21 C22 119.14(15) . . ? C20 C21 H21 120.4 . . ? C22 C21 H21 120.4 . . ? C21 C22 C17 120.75(15) . . ? C21 C22 H22 119.6 . . ? C17 C22 H22 119.6 . . ? O2 C23 H23A 109.5 . . ? O2 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? O2 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? 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 C9 N1 C1 C6 1.4(2) . . . . ? C9 N1 C1 C2 -178.65(14) . . . . ? N1 C1 C2 C3 157.81(15) . . . . ? C6 C1 C2 C3 -22.2(2) . . . . ? C1 C2 C3 C4 51.1(2) . . . . ? C2 C3 C4 C5 -63.6(2) . . . . ? C3 C4 C5 C6 45.3(2) . . . . ? N1 C1 C6 C7 1.3(2) . . . . ? C2 C1 C6 C7 -178.63(14) . . . . ? N1 C1 C6 C5 -175.25(15) . . . . ? C2 C1 C6 C5 4.8(2) . . . . ? C4 C5 C6 C1 -16.4(2) . . . . ? C4 C5 C6 C7 167.19(15) . . . . ? C1 C6 C7 C8 -1.4(2) . . . . ? C5 C6 C7 C8 175.22(14) . . . . ? C1 C6 C7 C17 -179.03(14) . . . . ? C5 C6 C7 C17 -2.4(2) . . . . ? C6 C7 C8 C9 -1.1(2) . . . . ? C17 C7 C8 C9 176.48(14) . . . . ? C6 C7 C8 C10 -178.65(14) . . . . ? C17 C7 C8 C10 -1.1(2) . . . . ? C1 N1 C9 N2 172.93(14) . . . . ? C1 N1 C9 C8 -4.1(2) . . . . ? C11 N2 C9 N1 158.74(14) . . . . ? C11 N2 C9 C8 -24.2(2) . . . . ? C7 C8 C9 N1 4.0(2) . . . . ? C10 C8 C9 N1 -178.35(14) . . . . ? C7 C8 C9 N2 -172.91(14) . . . . ? C10 C8 C9 N2 4.7(2) . . . . ? C11 N3 C10 O1 -167.31(17) . . . . ? C11 N3 C10 C8 13.4(3) . . . . ? C7 C8 C10 O1 -0.7(3) . . . . ? C9 C8 C10 O1 -178.28(16) . . . . ? C7 C8 C10 N3 178.55(16) . . . . ? C9 C8 C10 N3 1.0(2) . . . . ? C10 N3 C11 N2 -29.2(2) . . . . ? C10 N3 C11 C12 -148.67(18) . . . . ? C10 N3 C11 C16 91.9(2) . . . . ? C9 N2 C11 N3 33.4(2) . . . . ? C9 N2 C11 C12 150.18(14) . . . . ? C9 N2 C11 C16 -86.99(18) . . . . ? N3 C11 C12 C13 -170.69(14) . . . . ? N2 C11 C12 C13 71.96(18) . . . . ? C16 C11 C12 C13 -51.41(18) . . . . ? C11 C12 C13 C14 54.01(19) . . . . ? C12 C13 C14 C15 -56.51(19) . . . . ? C13 C14 C15 C16 58.4(2) . . . . ? C14 C15 C16 C11 -57.0(2) . . . . ? N3 C11 C16 C15 169.89(14) . . . . ? N2 C11 C16 C15 -70.98(18) . . . . ? C12 C11 C16 C15 52.43(18) . . . . ? C8 C7 C17 C18 93.25(19) . . . . ? C6 C7 C17 C18 -89.15(18) . . . . ? C8 C7 C17 C22 -88.44(19) . . . . ? C6 C7 C17 C22 89.17(18) . . . . ? C22 C17 C18 C19 2.7(2) . . . . ? C7 C17 C18 C19 -179.02(14) . . . . ? C17 C18 C19 C20 -0.9(2) . . . . ? C18 C19 C20 C21 -1.1(2) . . . . ? C18 C19 C20 Cl1 179.81(13) . . . . ? C19 C20 C21 C22 1.3(2) . . . . ? Cl1 C20 C21 C22 -179.58(13) . . . . ? C20 C21 C22 C17 0.5(2) . . . . ? C18 C17 C22 C21 -2.4(2) . . . . ? C7 C17 C22 C21 179.20(14) . . . . ? _diffrn_measured_fraction_theta_max 0.968 _diffrn_reflns_theta_full 29.14 _diffrn_measured_fraction_theta_full 0.968 _refine_diff_density_max 0.400 _refine_diff_density_min -0.321 _refine_diff_density_rms 0.058