# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_cambridge 0177 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Gregory Savage' _publ_contact_author_email paul.savage@csiro.au loop_ _publ_author_name S.Harding G.Savage data_mx113_11 _database_code_depnum_ccdc_archive 'CCDC 866125' #TrackingRef '- MX113_11 (compound 4b)Revised.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C19 H16 Cl2 N2 O3' _chemical_formula_sum 'C19 H16 Cl2 N2 O3' _chemical_formula_weight 391.24 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' Cl Cl 0.1484 0.1585 '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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 2/c' _symmetry_space_group_name_Hall '-C 2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 29.5615(10) _cell_length_b 12.2972(3) _cell_length_c 10.5852(4) _cell_angle_alpha 90.00 _cell_angle_beta 110.902(4) _cell_angle_gamma 90.00 _cell_volume 3594.7(2) _cell_formula_units_Z 8 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used 7150 _cell_measurement_theta_min 2.0553 _cell_measurement_theta_max 32.3817 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.446 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1616 _exptl_absorpt_coefficient_mu 0.383 _exptl_absorpt_correction_T_min 0.88908 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET) (compiled Aug 3 2011,13:03:54) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 123(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Ruby, Gemini ultra' _diffrn_detector_area_resol_mean 10.3389 _diffrn_measurement_method '\w scans' _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 22558 _diffrn_reflns_av_R_equivalents 0.0229 _diffrn_reflns_av_sigmaI/netI 0.0230 _diffrn_reflns_limit_h_min -42 _diffrn_reflns_limit_h_max 42 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.54 _diffrn_reflns_theta_max 32.45 _reflns_number_total 5930 _reflns_number_gt 4826 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET) (compiled Aug 3 2011,13:03:54) ; _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET) (compiled Aug 3 2011,13:03:54) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET) (compiled Aug 3 2011,13:03:54) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics X-SEED _computing_publication_material CIFTAB _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^)+(0.0394P)^2^+3.4062P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5930 _refine_ls_number_parameters 237 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0515 _refine_ls_R_factor_gt 0.0385 _refine_ls_wR_factor_ref 0.1002 _refine_ls_wR_factor_gt 0.0915 _refine_ls_goodness_of_fit_ref 1.027 _refine_ls_restrained_S_all 1.027 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl 0.054940(15) -0.24596(4) -0.09773(5) 0.05821(15) Uani 1 1 d . . . Cl2 Cl -0.014870(13) -0.15899(4) 0.04625(5) 0.04841(12) Uani 1 1 d . . . O1 O 0.20484(3) 0.13776(7) 0.35821(8) 0.02130(16) Uani 1 1 d . . . O2 O 0.26943(3) -0.06227(7) 0.36397(8) 0.01994(16) Uani 1 1 d . . . O3 O 0.21634(3) -0.19677(7) 0.35176(8) 0.02333(17) Uani 1 1 d . . . N1 N 0.16985(4) 0.22046(8) 0.29823(10) 0.02178(19) Uani 1 1 d . . . N2 N 0.19202(3) -0.03199(7) 0.24422(9) 0.01805(17) Uani 1 1 d . . . C1 C 0.16170(4) 0.22342(9) 0.17068(11) 0.0187(2) Uani 1 1 d . . . C2 C 0.19142(4) 0.14396(9) 0.12576(11) 0.01773(19) Uani 1 1 d . . . H2A H 0.2167 0.1813 0.1007 0.021 Uiso 1 1 calc R . . H2B H 0.1709 0.0997 0.0484 0.021 Uiso 1 1 calc R . . C3 C 0.21352(4) 0.07500(8) 0.25236(10) 0.01669(18) Uani 1 1 d . . . C4 C 0.26776(4) 0.04293(9) 0.29541(11) 0.01825(19) Uani 1 1 d . . . C5 C 0.22487(4) -0.10583(9) 0.32250(10) 0.01815(19) Uani 1 1 d . . . C6 C 0.12714(4) 0.30041(9) 0.08020(12) 0.0210(2) Uani 1 1 d . . . C7 C 0.09874(4) 0.36852(10) 0.12769(14) 0.0268(2) Uani 1 1 d . . . H7 H 0.1013 0.3649 0.2196 0.032 Uiso 1 1 calc R . . C8 C 0.06691(5) 0.44132(11) 0.04015(16) 0.0340(3) Uani 1 1 d . . . H8 H 0.0477 0.4876 0.0725 0.041 Uiso 1 1 calc R . . C9 C 0.06294(5) 0.44705(12) -0.09450(16) 0.0374(3) Uani 1 1 d . . . H9 H 0.0412 0.4973 -0.1538 0.045 Uiso 1 1 calc R . . C10 C 0.09072(5) 0.37948(12) -0.14220(15) 0.0353(3) Uani 1 1 d . . . H10 H 0.0878 0.3830 -0.2345 0.042 Uiso 1 1 calc R . . C11 C 0.12298(5) 0.30639(10) -0.05521(13) 0.0267(2) Uani 1 1 d . . . H11 H 0.1422 0.2605 -0.0881 0.032 Uiso 1 1 calc R . . C12 C 0.30281(4) 0.11910(10) 0.39485(12) 0.0251(2) Uani 1 1 d . . . H12A H 0.3354 0.0878 0.4248 0.038 Uiso 1 1 calc R . . H12B H 0.2929 0.1295 0.4731 0.038 Uiso 1 1 calc R . . H12C H 0.3028 0.1894 0.3512 0.038 Uiso 1 1 calc R . . C13 C 0.28182(4) 0.02019(10) 0.17312(11) 0.0233(2) Uani 1 1 d . . . H13A H 0.2573 -0.0266 0.1095 0.035 Uiso 1 1 calc R . . H13B H 0.3133 -0.0164 0.2024 0.035 Uiso 1 1 calc R . . H13C H 0.2839 0.0889 0.1286 0.035 Uiso 1 1 calc R . . C14 C 0.14160(4) -0.05659(9) 0.19276(11) 0.01885(19) Uani 1 1 d . . . C15 C 0.12421(4) -0.12751(9) 0.08408(12) 0.0226(2) Uani 1 1 d . . . H15 H 0.1452 -0.1548 0.0415 0.027 Uiso 1 1 calc R . . C16 C 0.07578(5) -0.15824(10) 0.03805(13) 0.0273(2) Uani 1 1 d . . . C17 C 0.04493(5) -0.11819(11) 0.09949(15) 0.0298(3) Uani 1 1 d . . . C18 C 0.06241(5) -0.04506(12) 0.20557(16) 0.0355(3) Uani 1 1 d . . . H18 H 0.0411 -0.0158 0.2461 0.043 Uiso 1 1 calc R . . C19 C 0.11069(5) -0.01429(11) 0.25303(14) 0.0285(3) Uani 1 1 d . . . H19 H 0.1225 0.0354 0.3262 0.034 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.0365(2) 0.0720(3) 0.0616(3) -0.0432(2) 0.01196(19) -0.01872(19) Cl2 0.02270(16) 0.0522(2) 0.0697(3) -0.0133(2) 0.01563(17) -0.01432(15) O1 0.0258(4) 0.0222(4) 0.0163(3) -0.0007(3) 0.0080(3) 0.0041(3) O2 0.0195(4) 0.0214(4) 0.0175(3) 0.0031(3) 0.0049(3) 0.0019(3) O3 0.0295(4) 0.0185(4) 0.0227(4) 0.0029(3) 0.0101(3) 0.0017(3) N1 0.0211(4) 0.0206(4) 0.0239(5) -0.0003(4) 0.0083(4) 0.0028(4) N2 0.0171(4) 0.0170(4) 0.0195(4) 0.0018(3) 0.0058(3) -0.0005(3) C1 0.0169(5) 0.0177(4) 0.0216(5) -0.0005(4) 0.0071(4) -0.0014(4) C2 0.0186(5) 0.0186(4) 0.0159(4) 0.0014(4) 0.0061(4) 0.0005(4) C3 0.0182(5) 0.0174(4) 0.0150(4) -0.0004(3) 0.0067(4) -0.0011(4) C4 0.0174(5) 0.0215(5) 0.0155(4) 0.0018(4) 0.0054(4) 0.0001(4) C5 0.0215(5) 0.0197(5) 0.0142(4) -0.0004(4) 0.0075(4) 0.0020(4) C6 0.0164(5) 0.0186(5) 0.0258(5) 0.0004(4) 0.0047(4) -0.0012(4) C7 0.0200(5) 0.0263(5) 0.0315(6) -0.0045(5) 0.0058(5) 0.0016(4) C8 0.0222(6) 0.0296(6) 0.0429(8) -0.0060(6) 0.0027(5) 0.0069(5) C9 0.0276(6) 0.0314(7) 0.0403(7) 0.0032(6) -0.0037(6) 0.0088(5) C10 0.0340(7) 0.0355(7) 0.0296(6) 0.0075(5) 0.0032(5) 0.0076(6) C11 0.0254(6) 0.0269(6) 0.0259(6) 0.0041(5) 0.0068(5) 0.0044(5) C12 0.0226(5) 0.0298(6) 0.0192(5) 0.0010(4) 0.0030(4) -0.0061(4) C13 0.0206(5) 0.0327(6) 0.0184(5) 0.0021(4) 0.0093(4) 0.0030(4) C14 0.0181(5) 0.0188(4) 0.0197(5) 0.0021(4) 0.0069(4) -0.0012(4) C15 0.0213(5) 0.0222(5) 0.0238(5) -0.0017(4) 0.0074(4) 0.0000(4) C16 0.0244(6) 0.0251(5) 0.0289(6) -0.0051(5) 0.0052(5) -0.0043(4) C17 0.0196(5) 0.0300(6) 0.0395(7) -0.0023(5) 0.0103(5) -0.0065(5) C18 0.0260(6) 0.0398(7) 0.0477(8) -0.0121(6) 0.0220(6) -0.0078(5) C19 0.0257(6) 0.0326(6) 0.0319(6) -0.0086(5) 0.0161(5) -0.0074(5) _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 C16 1.7255(13) . ? Cl2 C17 1.7272(13) . ? O1 N1 1.4278(12) . ? O1 C3 1.4568(13) . ? O2 C5 1.3426(14) . ? O2 C4 1.4754(13) . ? O3 C5 1.2107(13) . ? N1 C1 1.2846(15) . ? N2 C5 1.3711(14) . ? N2 C14 1.4248(14) . ? N2 C3 1.4503(13) . ? C1 C6 1.4693(15) . ? C1 C2 1.5004(15) . ? C2 C3 1.5222(15) . ? C3 C4 1.5531(15) . ? C4 C12 1.5102(16) . ? C4 C13 1.5202(15) . ? C6 C11 1.3960(17) . ? C6 C7 1.4002(17) . ? C7 C8 1.3868(18) . ? C8 C9 1.390(2) . ? C9 C10 1.384(2) . ? C10 C11 1.3923(18) . ? C14 C15 1.3879(16) . ? C14 C19 1.3888(16) . ? C15 C16 1.3902(17) . ? C16 C17 1.3858(19) . ? C17 C18 1.387(2) . ? C18 C19 1.3860(18) . ? 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 N1 O1 C3 109.50(8) . . ? C5 O2 C4 109.40(8) . . ? C1 N1 O1 108.78(9) . . ? C5 N2 C14 120.60(9) . . ? C5 N2 C3 111.34(9) . . ? C14 N2 C3 126.29(9) . . ? N1 C1 C6 121.97(10) . . ? N1 C1 C2 113.78(10) . . ? C6 C1 C2 124.23(10) . . ? C1 C2 C3 101.52(8) . . ? N2 C3 O1 109.42(8) . . ? N2 C3 C2 114.31(9) . . ? O1 C3 C2 104.12(8) . . ? N2 C3 C4 99.89(8) . . ? O1 C3 C4 110.83(8) . . ? C2 C3 C4 118.27(9) . . ? O2 C4 C12 107.87(9) . . ? O2 C4 C13 106.63(9) . . ? C12 C4 C13 112.30(9) . . ? O2 C4 C3 102.53(8) . . ? C12 C4 C3 115.26(9) . . ? C13 C4 C3 111.36(9) . . ? O3 C5 O2 123.68(10) . . ? O3 C5 N2 126.81(11) . . ? O2 C5 N2 109.52(9) . . ? C11 C6 C7 119.50(11) . . ? C11 C6 C1 119.30(10) . . ? C7 C6 C1 121.19(11) . . ? C8 C7 C6 119.81(13) . . ? C7 C8 C9 120.46(13) . . ? C10 C9 C8 119.98(13) . . ? C9 C10 C11 120.12(14) . . ? C10 C11 C6 120.12(12) . . ? C15 C14 C19 120.41(11) . . ? C15 C14 N2 118.55(10) . . ? C19 C14 N2 120.98(10) . . ? C14 C15 C16 119.47(11) . . ? C17 C16 C15 120.46(11) . . ? C17 C16 Cl1 120.92(10) . . ? C15 C16 Cl1 118.61(10) . . ? C16 C17 C18 119.53(11) . . ? C16 C17 Cl2 120.80(10) . . ? C18 C17 Cl2 119.67(10) . . ? C19 C18 C17 120.57(12) . . ? C18 C19 C14 119.51(12) . . ? _diffrn_measured_fraction_theta_max 0.914 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.470 _refine_diff_density_min -0.663 _refine_diff_density_rms 0.051 # Attachment '- MX114_11 (compound 3c)Revised.CIF' data_mx114_11 _database_code_depnum_ccdc_archive 'CCDC 866126' #TrackingRef '- MX114_11 (compound 3c)Revised.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H17 N O2' _chemical_formula_sum 'C14 H17 N O2' _chemical_formula_weight 231.29 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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' 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 9.9538(3) _cell_length_b 14.0904(4) _cell_length_c 9.3597(3) _cell_angle_alpha 90.00 _cell_angle_beta 105.647(3) _cell_angle_gamma 90.00 _cell_volume 1264.08(7) _cell_formula_units_Z 4 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used 5904 _cell_measurement_theta_min 2.1205 _cell_measurement_theta_max 32.1124 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.215 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 496 _exptl_absorpt_coefficient_mu 0.081 _exptl_absorpt_correction_T_min 0.72431 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.36 (release 02-08-2010 CrysAlis171 .NET) (compiled Aug 2 2010,13:00:58) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 123(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Ruby, Gemini ultra' _diffrn_detector_area_resol_mean 10.3389 _diffrn_measurement_method '\w scans' _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15445 _diffrn_reflns_av_R_equivalents 0.0249 _diffrn_reflns_av_sigmaI/netI 0.0263 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.12 _diffrn_reflns_theta_max 32.19 _reflns_number_total 4197 _reflns_number_gt 3371 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.36 (release 02-08-2010 CrysAlis171 .NET) (compiled Aug 2 2010,13:00:58) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.36 (release 02-08-2010 CrysAlis171 .NET) (compiled Aug 2 2010,13:00:58) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.36 (release 02-08-2010 CrysAlis171 .NET) (compiled Aug 2 2010,13:00:58) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics X-SEED _computing_publication_material CIFTAB _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^)+(0.0580P)^2^+0.3390P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4197 _refine_ls_number_parameters 156 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0574 _refine_ls_R_factor_gt 0.0447 _refine_ls_wR_factor_ref 0.1280 _refine_ls_wR_factor_gt 0.1184 _refine_ls_goodness_of_fit_ref 1.052 _refine_ls_restrained_S_all 1.052 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.45235(7) 0.01265(5) 0.23570(8) 0.02214(17) Uani 1 1 d . . . O2 O 0.62525(9) -0.07531(6) 0.38093(10) 0.0295(2) Uani 1 1 d . . . N1 N 0.64553(8) 0.08706(6) 0.35813(9) 0.01752(17) Uani 1 1 d . . . C1 C 0.58016(10) 0.00071(7) 0.33116(11) 0.01892(19) Uani 1 1 d . . . C2 C 0.42739(10) 0.11342(7) 0.19558(11) 0.01966(19) Uani 1 1 d . . . C3 C 0.55993(10) 0.16111(7) 0.28521(11) 0.01896(19) Uani 1 1 d . . . C4 C 0.78235(10) 0.10037(7) 0.45621(10) 0.01660(18) Uani 1 1 d . . . C5 C 0.89455(10) 0.11646(7) 0.39656(11) 0.01912(19) Uani 1 1 d . . . C6 C 1.02510(11) 0.12849(8) 0.49768(12) 0.0235(2) Uani 1 1 d . . . H6 H 1.1044 0.1387 0.4616 0.028 Uiso 1 1 calc R . . C7 C 1.04166(11) 0.12592(8) 0.64935(12) 0.0240(2) Uani 1 1 d . . . H7 H 1.1320 0.1344 0.7150 0.029 Uiso 1 1 calc R . . C8 C 0.92839(11) 0.11121(7) 0.70751(11) 0.0210(2) Uani 1 1 d . . . C9 C 0.79771(10) 0.09795(7) 0.60818(11) 0.01898(19) Uani 1 1 d . . . H9 H 0.7186 0.0872 0.6445 0.023 Uiso 1 1 calc R . . C10 C 0.87688(12) 0.11890(9) 0.23211(12) 0.0261(2) Uani 1 1 d . . . H10A H 0.8278 0.0616 0.1866 0.039 Uiso 1 1 calc R . . H10B H 0.9688 0.1217 0.2127 0.039 Uiso 1 1 calc R . . H10C H 0.8226 0.1750 0.1897 0.039 Uiso 1 1 calc R . . C11 C 0.94594(13) 0.11007(9) 0.87263(12) 0.0298(2) Uani 1 1 d . . . H11A H 0.9519 0.1754 0.9098 0.045 Uiso 1 1 calc R . . H11B H 1.0316 0.0758 0.9219 0.045 Uiso 1 1 calc R . . H11C H 0.8657 0.0783 0.8935 0.045 Uiso 1 1 calc R . . C12 C 0.59027(12) 0.25247(8) 0.29469(14) 0.0287(2) Uani 1 1 d . . . H12A H 0.6777 0.2735 0.3557 0.034 Uiso 1 1 calc R . . H12B H 0.5247 0.2972 0.2405 0.034 Uiso 1 1 calc R . . C13 C 0.29973(11) 0.14440(10) 0.24241(14) 0.0302(2) Uani 1 1 d . . . H13A H 0.2171 0.1119 0.1812 0.045 Uiso 1 1 calc R . . H13B H 0.2876 0.2132 0.2293 0.045 Uiso 1 1 calc R . . H13C H 0.3120 0.1282 0.3470 0.045 Uiso 1 1 calc R . . C14 C 0.40795(14) 0.12157(10) 0.02952(13) 0.0326(3) Uani 1 1 d . . . H14A H 0.3210 0.0900 -0.0233 0.049 Uiso 1 1 calc R . . H14B H 0.4867 0.0913 0.0033 0.049 Uiso 1 1 calc R . . H14C H 0.4035 0.1887 0.0013 0.049 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0167(3) 0.0227(4) 0.0239(4) 0.0008(3) 0.0001(3) -0.0020(3) O2 0.0271(4) 0.0181(4) 0.0365(5) 0.0035(3) -0.0032(3) -0.0031(3) N1 0.0144(4) 0.0156(4) 0.0206(4) 0.0015(3) 0.0013(3) -0.0005(3) C1 0.0171(4) 0.0199(5) 0.0187(4) 0.0000(3) 0.0029(3) -0.0025(3) C2 0.0168(4) 0.0231(5) 0.0178(4) 0.0022(3) 0.0026(3) 0.0023(3) C3 0.0157(4) 0.0207(5) 0.0202(4) 0.0031(3) 0.0044(3) 0.0027(3) C4 0.0146(4) 0.0147(4) 0.0192(4) 0.0004(3) 0.0023(3) -0.0002(3) C5 0.0175(4) 0.0178(4) 0.0224(5) 0.0022(3) 0.0061(3) 0.0011(3) C6 0.0155(4) 0.0235(5) 0.0317(5) 0.0038(4) 0.0068(4) -0.0006(4) C7 0.0170(5) 0.0210(5) 0.0290(5) 0.0014(4) -0.0020(4) -0.0012(3) C8 0.0236(5) 0.0161(4) 0.0203(5) -0.0002(3) 0.0008(4) 0.0012(3) C9 0.0186(4) 0.0181(4) 0.0200(4) 0.0005(3) 0.0049(3) -0.0001(3) C10 0.0259(5) 0.0308(6) 0.0237(5) 0.0033(4) 0.0104(4) 0.0027(4) C11 0.0362(6) 0.0287(6) 0.0201(5) -0.0008(4) -0.0001(4) 0.0041(4) C12 0.0232(5) 0.0201(5) 0.0403(6) 0.0049(4) 0.0042(4) 0.0039(4) C13 0.0168(5) 0.0401(7) 0.0331(6) -0.0027(5) 0.0057(4) 0.0052(4) C14 0.0349(6) 0.0420(7) 0.0183(5) 0.0044(4) 0.0028(4) 0.0019(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.3535(12) . ? O1 C2 1.4726(12) . ? O2 C1 1.2054(12) . ? N1 C1 1.3707(12) . ? N1 C3 1.4024(12) . ? N1 C4 1.4346(12) . ? C2 C13 1.5160(15) . ? C2 C3 1.5162(14) . ? C2 C14 1.5180(14) . ? C3 C12 1.3198(15) . ? C4 C9 1.3894(13) . ? C4 C5 1.3952(13) . ? C5 C6 1.3963(14) . ? C5 C10 1.5018(14) . ? C6 C7 1.3847(16) . ? C7 C8 1.3934(15) . ? C8 C9 1.3924(14) . ? C8 C11 1.5079(15) . ? 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 C1 O1 C2 110.61(7) . . ? C1 N1 C3 112.01(8) . . ? C1 N1 C4 123.74(8) . . ? C3 N1 C4 124.16(8) . . ? O2 C1 O1 123.45(9) . . ? O2 C1 N1 127.51(9) . . ? O1 C1 N1 109.04(8) . . ? O1 C2 C13 107.51(9) . . ? O1 C2 C3 102.98(7) . . ? C13 C2 C3 112.61(9) . . ? O1 C2 C14 107.47(9) . . ? C13 C2 C14 112.89(9) . . ? C3 C2 C14 112.62(9) . . ? C12 C3 N1 126.51(10) . . ? C12 C3 C2 128.22(9) . . ? N1 C3 C2 105.27(8) . . ? C9 C4 C5 122.32(9) . . ? C9 C4 N1 118.37(8) . . ? C5 C4 N1 119.30(8) . . ? C4 C5 C6 116.59(9) . . ? C4 C5 C10 121.92(9) . . ? C6 C5 C10 121.48(9) . . ? C7 C6 C5 121.56(9) . . ? C6 C7 C8 121.28(9) . . ? C9 C8 C7 117.89(9) . . ? C9 C8 C11 120.80(10) . . ? C7 C8 C11 121.31(10) . . ? C4 C9 C8 120.35(9) . . ? _diffrn_measured_fraction_theta_max 0.944 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.370 _refine_diff_density_min -0.204 _refine_diff_density_rms 0.045