# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 loop_ _publ_author_name _publ_author_address 'Yun Chen' ; College of Chemistry and Chemical Engineering, Hunan University, Changsha, Hunan, 410082, People's Republic of China. ; 'Shuanglian Cai' ; College of Chemistry and Chemical Engineering, Hunan University, Changsha, Hunan, 410082, People's Republic of China. ; 'Hui Li' ; College of Chemistry and Chemical Engineering, Hunan University, Changsha, Hunan, 410082, People's Republic of China. ; _publ_contact_author_name 'Yun Chen' _publ_contact_author_email CNCHENYUN@YAHOO.COM.CN _publ_section_title ; Luminescent N-arylphthalimidino derivatives 2- and 4- (1-oxo-1H-2,3-dihydroisoindol-2-yl)benzoic acid: examples of a new class of reaction induced crystallization for organic compound ; _publ_contact_author_address ; College of Chemistry and Chemical Engineering, Hunan University, Changsha, Hunan, 410082, People's Republic of China ; _publ_contact_author_fax +86-731-8822242 _publ_contact_author_phone +86-731-8713642 # Attachment 'c524.cif' data_c _database_code_depnum_ccdc_archive 'CCDC 714749' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C15 H11 N O3' _chemical_formula_sum 'C15 H11 N O3' _chemical_formula_weight 253.25 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 Triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.4222(3) _cell_length_b 10.2231(2) _cell_length_c 10.3311(4) _cell_angle_alpha 64.642(2) _cell_angle_beta 74.415(2) _cell_angle_gamma 76.328(2) _cell_volume 584.64(4) _cell_formula_units_Z 2 _cell_measurement_temperature 273(2) _cell_measurement_reflns_used 3082 _cell_measurement_theta_min 2.22 _cell_measurement_theta_max 25.05 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.439 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 264 _exptl_absorpt_coefficient_mu 0.101 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9820 _exptl_absorpt_correction_T_max 0.9859 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 273(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Siemens SMART CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3082 _diffrn_reflns_av_R_equivalents 0.0457 _diffrn_reflns_av_sigmaI/netI 0.0566 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.22 _diffrn_reflns_theta_max 25.05 _reflns_number_total 2058 _reflns_number_gt 1421 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Siemens, 1996)' _computing_cell_refinement 'SMART (Siemens, 1996)' _computing_data_reduction 'XPREP/SAINT(Siemens, 1994)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'DIAMOND (Brandenburg, 2005)' _computing_publication_material 'SHELXTL (Sheldrick, 2008)' _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^)+(0.0481P)^2^+3.9429P] 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 2058 _refine_ls_number_parameters 176 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1683 _refine_ls_R_factor_gt 0.1181 _refine_ls_wR_factor_ref 0.2899 _refine_ls_wR_factor_gt 0.2517 _refine_ls_goodness_of_fit_ref 1.049 _refine_ls_restrained_S_all 1.048 _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 0.1786(8) 0.6628(6) 0.3191(5) 0.0639(15) Uani 1 1 d . . . C1 C 0.3055(10) 0.6824(8) 0.3768(7) 0.0452(16) Uani 1 1 d . . . C2 C 0.2824(10) 0.6481(7) 0.5334(7) 0.0431(16) Uani 1 1 d . . . C3 C 0.1143(11) 0.5874(8) 0.6474(7) 0.0524(18) Uani 1 1 d . . . H3A H -0.0036 0.5616 0.6318 0.063 Uiso 1 1 calc R . . C4 C 0.1333(13) 0.5679(9) 0.7844(8) 0.060(2) Uani 1 1 d . . . H4A H 0.0224 0.5306 0.8631 0.072 Uiso 1 1 calc R . . C5 C 0.3108(12) 0.6017(9) 0.8088(8) 0.061(2) Uani 1 1 d . . . H5A H 0.3195 0.5845 0.9033 0.074 Uiso 1 1 calc R . . C6 C 0.4765(12) 0.6610(8) 0.6940(8) 0.0558(19) Uani 1 1 d . . . H6A H 0.5959 0.6845 0.7102 0.067 Uiso 1 1 calc R . . C7 C 0.4604(10) 0.6846(7) 0.5543(7) 0.0437(16) Uani 1 1 d . . . C8 C 0.6133(11) 0.7451(9) 0.4112(7) 0.0500(18) Uani 1 1 d . . . H8A H 0.6311 0.8447 0.3885 0.060 Uiso 1 1 calc R . . H8B H 0.7554 0.6854 0.4119 0.060 Uiso 1 1 calc R . . C9 C 0.5911(9) 0.7851(7) 0.1573(7) 0.0387(15) Uani 1 1 d . . . C10 C 0.8033(10) 0.8217(8) 0.1083(7) 0.0466(17) Uani 1 1 d . . . H10A H 0.8829 0.8138 0.1750 0.056 Uiso 1 1 calc R . . C11 C 0.8950(10) 0.8693(8) -0.0386(7) 0.0469(17) Uani 1 1 d . . . H11A H 1.0366 0.8924 -0.0699 0.056 Uiso 1 1 calc R . . C12 C 0.7779(10) 0.8830(7) -0.1397(7) 0.0436(16) Uani 1 1 d . . . C13 C 0.5654(10) 0.8478(8) -0.0899(7) 0.0478(17) Uani 1 1 d . . . H13A H 0.4845 0.8567 -0.1564 0.057 Uiso 1 1 calc R . . C14 C 0.4758(10) 0.8004(7) 0.0550(7) 0.0450(16) Uani 1 1 d . . . H14A H 0.3339 0.7779 0.0859 0.054 Uiso 1 1 calc R . . C15 C 0.8742(10) 0.9374(7) -0.2965(7) 0.0436(16) Uani 1 1 d . . . O3 O 1.0641(8) 0.9746(6) -0.3360(6) 0.0636(15) Uani 1 1 d D . . O2 O 0.7664(8) 0.9440(6) -0.3863(5) 0.0613(15) Uani 1 1 d . . . N1 N 0.5016(8) 0.7389(6) 0.3069(5) 0.0416(13) Uani 1 1 d . . . H3B H 1.122(16) 1.000(12) -0.432(4) 0.13(4) Uiso 1 1 d 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 O1 0.043(3) 0.097(4) 0.051(3) -0.019(3) -0.005(2) -0.034(3) C1 0.035(3) 0.056(4) 0.039(4) -0.010(3) -0.005(3) -0.013(3) C2 0.034(3) 0.051(4) 0.044(4) -0.018(3) -0.008(3) -0.006(3) C3 0.041(4) 0.063(5) 0.046(4) -0.015(4) 0.003(3) -0.021(3) C4 0.058(5) 0.067(5) 0.044(4) -0.015(4) 0.005(3) -0.018(4) C5 0.063(5) 0.075(6) 0.042(4) -0.019(4) -0.005(4) -0.017(4) C6 0.050(4) 0.066(5) 0.055(5) -0.026(4) -0.005(3) -0.016(4) C7 0.041(4) 0.050(4) 0.039(4) -0.015(3) -0.005(3) -0.011(3) C8 0.041(4) 0.071(5) 0.043(4) -0.022(4) -0.009(3) -0.017(3) C9 0.031(3) 0.044(4) 0.040(4) -0.014(3) -0.005(3) -0.010(3) C10 0.036(3) 0.061(4) 0.041(4) -0.015(3) -0.008(3) -0.013(3) C11 0.035(3) 0.059(4) 0.043(4) -0.014(3) -0.002(3) -0.018(3) C12 0.040(4) 0.047(4) 0.038(4) -0.014(3) 0.002(3) -0.011(3) C13 0.041(4) 0.062(5) 0.045(4) -0.022(3) -0.010(3) -0.011(3) C14 0.035(3) 0.060(4) 0.038(4) -0.017(3) -0.002(3) -0.011(3) C15 0.038(3) 0.044(4) 0.048(4) -0.021(3) 0.000(3) -0.007(3) O3 0.051(3) 0.090(4) 0.051(3) -0.027(3) 0.006(2) -0.031(3) O2 0.055(3) 0.088(4) 0.040(3) -0.019(3) -0.002(2) -0.027(3) N1 0.030(3) 0.059(4) 0.034(3) -0.014(3) -0.002(2) -0.014(2) _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 O1 0.000(13) 1 ? O1 C1 1.224(8) . ? C1 O1 1.224(8) 1 ? C1 N1 1.393(8) . ? C1 C2 1.474(9) . ? C2 C7 1.377(9) . ? C2 C3 1.395(9) . ? C3 C4 1.378(10) . ? C3 H3A 0.9300 . ? C4 C5 1.378(10) . ? C4 H4A 0.9300 . ? C5 C6 1.385(10) . ? C5 H5A 0.9300 . ? C6 C7 1.386(9) . ? C6 H6A 0.9300 . ? C7 C8 1.502(9) . ? C8 N1 1.474(8) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 C14 1.383(9) . ? C9 C10 1.401(8) . ? C9 N1 1.403(8) . ? C10 C11 1.382(9) . ? C10 H10A 0.9300 . ? C11 C12 1.387(9) . ? C11 H11A 0.9300 . ? C12 C13 1.398(9) . ? C12 C15 1.473(9) . ? C13 C14 1.362(9) . ? C13 H13A 0.9300 . ? C14 H14A 0.9300 . ? C15 O2 1.270(8) . ? C15 O3 1.272(8) . ? O3 H3B 0.91(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 O1 O1 C1 0(10) 1 . ? O1 C1 O1 0.0(5) 1 . ? O1 C1 N1 126.4(6) 1 . ? O1 C1 N1 126.4(6) . . ? O1 C1 C2 126.7(6) 1 . ? O1 C1 C2 126.7(6) . . ? N1 C1 C2 106.9(5) . . ? C7 C2 C3 123.0(6) . . ? C7 C2 C1 108.8(6) . . ? C3 C2 C1 128.2(6) . . ? C4 C3 C2 116.0(7) . . ? C4 C3 H3A 122.0 . . ? C2 C3 H3A 122.0 . . ? C3 C4 C5 122.3(7) . . ? C3 C4 H4A 118.9 . . ? C5 C4 H4A 118.9 . . ? C4 C5 C6 120.6(7) . . ? C4 C5 H5A 119.7 . . ? C6 C5 H5A 119.7 . . ? C5 C6 C7 118.6(7) . . ? C5 C6 H6A 120.7 . . ? C7 C6 H6A 120.7 . . ? C2 C7 C6 119.5(6) . . ? C2 C7 C8 110.2(5) . . ? C6 C7 C8 130.3(6) . . ? N1 C8 C7 102.6(5) . . ? N1 C8 H8A 111.2 . . ? C7 C8 H8A 111.2 . . ? N1 C8 H8B 111.2 . . ? C7 C8 H8B 111.2 . . ? H8A C8 H8B 109.2 . . ? C14 C9 C10 118.4(6) . . ? C14 C9 N1 122.7(5) . . ? C10 C9 N1 118.9(5) . . ? C11 C10 C9 120.3(6) . . ? C11 C10 H10A 119.8 . . ? C9 C10 H10A 119.8 . . ? C10 C11 C12 120.6(6) . . ? C10 C11 H11A 119.7 . . ? C12 C11 H11A 119.7 . . ? C11 C12 C13 118.7(6) . . ? C11 C12 C15 120.4(6) . . ? C13 C12 C15 120.9(6) . . ? C14 C13 C12 120.6(6) . . ? C14 C13 H13A 119.7 . . ? C12 C13 H13A 119.7 . . ? C13 C14 C9 121.5(6) . . ? C13 C14 H14A 119.3 . . ? C9 C14 H14A 119.3 . . ? O2 C15 O3 122.8(6) . . ? O2 C15 C12 119.1(6) . . ? O3 C15 C12 118.1(6) . . ? C15 O3 H3B 115(7) . . ? C1 N1 C9 126.7(5) . . ? C1 N1 C8 111.5(5) . . ? C9 N1 C8 121.8(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 O1 O1 C1 N1 0.0(6) 1 . . . ? O1 O1 C1 C2 0.0(2) 1 . . . ? O1 C1 C2 C7 179.2(7) 1 . . . ? O1 C1 C2 C7 179.2(7) . . . . ? N1 C1 C2 C7 0.4(8) . . . . ? O1 C1 C2 C3 -0.1(12) 1 . . . ? O1 C1 C2 C3 -0.1(12) . . . . ? N1 C1 C2 C3 -179.0(7) . . . . ? C7 C2 C3 C4 1.2(11) . . . . ? C1 C2 C3 C4 -179.5(7) . . . . ? C2 C3 C4 C5 -2.0(12) . . . . ? C3 C4 C5 C6 1.7(13) . . . . ? C4 C5 C6 C7 -0.4(12) . . . . ? C3 C2 C7 C6 -0.1(11) . . . . ? C1 C2 C7 C6 -179.5(6) . . . . ? C3 C2 C7 C8 179.1(7) . . . . ? C1 C2 C7 C8 -0.3(8) . . . . ? C5 C6 C7 C2 -0.4(11) . . . . ? C5 C6 C7 C8 -179.4(7) . . . . ? C2 C7 C8 N1 0.1(8) . . . . ? C6 C7 C8 N1 179.2(7) . . . . ? C14 C9 C10 C11 -1.1(10) . . . . ? N1 C9 C10 C11 -179.1(6) . . . . ? C9 C10 C11 C12 0.6(11) . . . . ? C10 C11 C12 C13 0.1(10) . . . . ? C10 C11 C12 C15 178.5(6) . . . . ? C11 C12 C13 C14 -0.3(10) . . . . ? C15 C12 C13 C14 -178.7(6) . . . . ? C12 C13 C14 C9 -0.3(11) . . . . ? C10 C9 C14 C13 0.9(10) . . . . ? N1 C9 C14 C13 178.9(6) . . . . ? C11 C12 C15 O2 177.6(7) . . . . ? C13 C12 C15 O2 -4.0(10) . . . . ? C11 C12 C15 O3 -1.8(10) . . . . ? C13 C12 C15 O3 176.5(7) . . . . ? O1 C1 N1 C9 0.4(12) 1 . . . ? O1 C1 N1 C9 0.4(12) . . . . ? C2 C1 N1 C9 179.3(6) . . . . ? O1 C1 N1 C8 -179.2(7) 1 . . . ? O1 C1 N1 C8 -179.2(7) . . . . ? C2 C1 N1 C8 -0.3(8) . . . . ? C14 C9 N1 C1 10.1(10) . . . . ? C10 C9 N1 C1 -171.9(7) . . . . ? C14 C9 N1 C8 -170.3(7) . . . . ? C10 C9 N1 C8 7.6(9) . . . . ? C7 C8 N1 C1 0.1(8) . . . . ? C7 C8 N1 C9 -179.5(6) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A C14 H14A O1 0.93 2.24 2.872(8) 124.6 1 C10 H10A O1 0.93 2.52 3.336(8) 146.0 1_655 C3 H3A O1 0.93 2.59 3.371(9) 142.2 2_566 O3 H3B O2 0.91(2) 1.71(2) 2.611(7) 177(11) 2_774 _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 25.05 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.379 _refine_diff_density_min -0.299 _refine_diff_density_rms 0.083 # Attachment 'c526.cif' data_d _database_code_depnum_ccdc_archive 'CCDC 714750' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C15 H11 N O3' _chemical_formula_sum 'C15 H11 N O3' _chemical_formula_weight 253.25 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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' _symmetry_space_group_name_Hall 'P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 5.8831(13) _cell_length_b 11.837(3) _cell_length_c 17.492(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1218.1(5) _cell_formula_units_Z 4 _cell_measurement_temperature 273(2) _cell_measurement_reflns_used 3005 _cell_measurement_theta_min 2.8970 _cell_measurement_theta_max 25.0465 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.381 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 528 _exptl_absorpt_coefficient_mu 0.097 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9770 _exptl_absorpt_correction_T_max 0.9846 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 273(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Siemens SMART CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3005 _diffrn_reflns_av_R_equivalents 0.0640 _diffrn_reflns_av_sigmaI/netI 0.0567 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.90 _diffrn_reflns_theta_max 25.05 _reflns_number_total 1227 _reflns_number_gt 867 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Siemens, 1996)' _computing_cell_refinement 'SMART (Siemens, 1996)' _computing_data_reduction 'XPREP/SAINT(Siemens, 1994)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'DIAMOND (Brandenburg, 2005)' _computing_publication_material 'SHELXTL (Sheldrick, 2008)' _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^)+(0.0329P)^2^+2.8981P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -10(10) _refine_ls_number_reflns 1227 _refine_ls_number_parameters 176 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1152 _refine_ls_R_factor_gt 0.0709 _refine_ls_wR_factor_ref 0.1666 _refine_ls_wR_factor_gt 0.1423 _refine_ls_goodness_of_fit_ref 1.010 _refine_ls_restrained_S_all 1.009 _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 N1 N 0.4977(10) 0.6372(5) 0.2917(3) 0.0477(15) Uani 1 1 d . . . O1 O 0.8119(10) 0.5279(4) 0.2715(3) 0.0665(17) Uani 1 1 d . . . O2 O 0.8124(12) 0.8133(5) 0.2890(3) 0.086(2) Uani 1 1 d . . . O3 O 0.8831(12) 0.8891(6) 0.1779(3) 0.084(2) Uani 1 1 d D . . H3 H 0.998(11) 0.932(7) 0.198(5) 0.11(4) Uiso 1 1 d D . . C1 C 0.6773(14) 0.5740(6) 0.3146(4) 0.0484(19) Uani 1 1 d . . . C2 C 0.3654(13) 0.6845(7) 0.3545(4) 0.063(2) Uani 1 1 d . . . H2A H 0.2075 0.6612 0.3516 0.076 Uiso 1 1 calc R . . H2B H 0.3729 0.7664 0.3548 0.076 Uiso 1 1 calc R . . C3 C 0.4797(13) 0.6356(6) 0.4233(4) 0.0526(19) Uani 1 1 d . . . C4 C 0.4332(15) 0.6454(6) 0.5004(4) 0.064(2) Uani 1 1 d . . . H4 H 0.3076 0.6864 0.5170 0.077 Uiso 1 1 calc R . . C5 C 0.5746(17) 0.5939(7) 0.5525(4) 0.066(2) Uani 1 1 d . . . H5 H 0.5427 0.5992 0.6045 0.080 Uiso 1 1 calc R . . C6 C 0.7620(16) 0.5349(6) 0.5286(4) 0.066(2) Uani 1 1 d . . . H6 H 0.8579 0.5026 0.5648 0.079 Uiso 1 1 calc R . . C7 C 0.8110(15) 0.5225(6) 0.4520(4) 0.058(2) Uani 1 1 d . . . H7 H 0.9359 0.4806 0.4360 0.070 Uiso 1 1 calc R . . C8 C 0.6692(13) 0.5740(6) 0.4001(4) 0.0483(19) Uani 1 1 d . . . C9 C 0.4591(12) 0.6730(5) 0.2144(4) 0.0452(17) Uani 1 1 d . . . C10 C 0.5864(13) 0.7602(6) 0.1814(4) 0.0472(18) Uani 1 1 d . . . C11 C 0.5321(14) 0.7908(6) 0.1068(4) 0.056(2) Uani 1 1 d . . . H11 H 0.6162 0.8473 0.0830 0.067 Uiso 1 1 calc R . . C12 C 0.3592(15) 0.7405(6) 0.0675(4) 0.063(2) Uani 1 1 d . . . H12 H 0.3259 0.7638 0.0180 0.076 Uiso 1 1 calc R . . C13 C 0.2352(15) 0.6563(7) 0.1003(5) 0.070(2) Uani 1 1 d . . . H13 H 0.1184 0.6216 0.0732 0.084 Uiso 1 1 calc R . . C14 C 0.2849(15) 0.6228(6) 0.1747(4) 0.061(2) Uani 1 1 d . . . H14 H 0.1997 0.5660 0.1977 0.073 Uiso 1 1 calc R . . C15 C 0.7717(13) 0.8206(6) 0.2226(4) 0.0511(19) Uani 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 N1 0.043(4) 0.049(3) 0.051(3) 0.007(3) 0.013(3) 0.006(3) O1 0.064(4) 0.078(4) 0.058(3) 0.010(3) 0.014(3) 0.033(3) O2 0.104(5) 0.097(4) 0.056(3) 0.008(3) -0.019(4) -0.044(5) O3 0.091(5) 0.100(5) 0.062(3) 0.004(3) 0.002(3) -0.051(4) C1 0.048(5) 0.039(4) 0.058(4) 0.004(3) 0.008(4) 0.000(4) C2 0.056(5) 0.069(5) 0.065(4) 0.003(4) 0.003(5) 0.014(5) C3 0.048(5) 0.045(4) 0.065(4) -0.002(4) 0.008(4) -0.002(4) C4 0.068(6) 0.061(5) 0.063(4) -0.008(4) 0.022(5) 0.001(5) C5 0.091(7) 0.056(5) 0.053(4) 0.002(4) 0.009(5) -0.015(5) C6 0.088(7) 0.055(5) 0.054(5) 0.005(4) 0.003(5) -0.004(6) C7 0.061(6) 0.056(5) 0.058(4) 0.001(4) 0.004(4) 0.009(5) C8 0.047(5) 0.040(4) 0.058(4) 0.007(3) 0.002(4) -0.006(4) C9 0.044(5) 0.038(4) 0.053(4) 0.000(3) 0.001(4) 0.003(4) C10 0.048(5) 0.042(4) 0.052(4) -0.004(3) 0.004(4) 0.001(4) C11 0.061(6) 0.053(4) 0.055(4) 0.002(4) -0.003(4) -0.004(4) C12 0.075(6) 0.054(5) 0.061(5) 0.003(4) -0.018(5) -0.005(5) C13 0.070(6) 0.065(5) 0.075(5) 0.008(5) -0.021(5) -0.021(5) C14 0.056(5) 0.054(5) 0.073(5) 0.002(4) -0.005(4) -0.015(5) C15 0.058(5) 0.045(4) 0.050(4) -0.005(3) 0.006(4) -0.004(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C1 1.356(9) . ? N1 C9 1.434(8) . ? N1 C2 1.458(8) . ? O1 C1 1.222(8) . ? O2 C15 1.189(8) . ? O3 C15 1.303(9) . ? O3 H3 0.91(2) . ? C1 C8 1.496(9) . ? C2 C3 1.495(10) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 C4 1.382(9) . ? C3 C8 1.393(10) . ? C4 C5 1.376(10) . ? C4 H4 0.9300 . ? C5 C6 1.370(11) . ? C5 H5 0.9300 . ? C6 C7 1.378(9) . ? C6 H6 0.9300 . ? C7 C8 1.376(10) . ? C7 H7 0.9300 . ? C9 C14 1.373(10) . ? C9 C10 1.400(9) . ? C10 C11 1.391(9) . ? C10 C15 1.489(10) . ? C11 C12 1.365(10) . ? C11 H11 0.9300 . ? C12 C13 1.361(10) . ? C12 H12 0.9300 . ? C13 C14 1.392(10) . ? C13 H13 0.9300 . ? C14 H14 0.9300 . ? 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 N1 C9 124.4(6) . . ? C1 N1 C2 113.9(6) . . ? C9 N1 C2 120.8(6) . . ? C15 O3 H3 119(6) . . ? O1 C1 N1 124.7(6) . . ? O1 C1 C8 129.6(7) . . ? N1 C1 C8 105.8(6) . . ? N1 C2 C3 102.6(6) . . ? N1 C2 H2A 111.2 . . ? C3 C2 H2A 111.2 . . ? N1 C2 H2B 111.2 . . ? C3 C2 H2B 111.2 . . ? H2A C2 H2B 109.2 . . ? C4 C3 C8 119.2(7) . . ? C4 C3 C2 131.6(8) . . ? C8 C3 C2 109.2(6) . . ? C5 C4 C3 119.3(8) . . ? C5 C4 H4 120.3 . . ? C3 C4 H4 120.3 . . ? C6 C5 C4 120.7(7) . . ? C6 C5 H5 119.7 . . ? C4 C5 H5 119.7 . . ? C5 C6 C7 121.3(8) . . ? C5 C6 H6 119.4 . . ? C7 C6 H6 119.4 . . ? C8 C7 C6 117.9(8) . . ? C8 C7 H7 121.0 . . ? C6 C7 H7 121.0 . . ? C7 C8 C3 121.6(7) . . ? C7 C8 C1 129.9(8) . . ? C3 C8 C1 108.5(7) . . ? C14 C9 C10 120.7(6) . . ? C14 C9 N1 117.9(6) . . ? C10 C9 N1 121.4(6) . . ? C11 C10 C9 117.1(7) . . ? C11 C10 C15 119.7(7) . . ? C9 C10 C15 123.1(6) . . ? C12 C11 C10 122.0(8) . . ? C12 C11 H11 119.0 . . ? C10 C11 H11 119.0 . . ? C13 C12 C11 120.5(7) . . ? C13 C12 H12 119.8 . . ? C11 C12 H12 119.8 . . ? C12 C13 C14 119.3(8) . . ? C12 C13 H13 120.3 . . ? C14 C13 H13 120.3 . . ? C9 C14 C13 120.4(8) . . ? C9 C14 H14 119.8 . . ? C13 C14 H14 119.8 . . ? O2 C15 O3 122.0(8) . . ? O2 C15 C10 125.8(7) . . ? O3 C15 C10 112.2(6) . . ? 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 O1 -9.7(11) . . . . ? C2 N1 C1 O1 -179.0(7) . . . . ? C9 N1 C1 C8 170.7(6) . . . . ? C2 N1 C1 C8 1.4(8) . . . . ? C1 N1 C2 C3 -3.5(8) . . . . ? C9 N1 C2 C3 -173.2(6) . . . . ? N1 C2 C3 C4 -178.3(8) . . . . ? N1 C2 C3 C8 4.3(8) . . . . ? C8 C3 C4 C5 -0.2(11) . . . . ? C2 C3 C4 C5 -177.4(8) . . . . ? C3 C4 C5 C6 1.0(12) . . . . ? C4 C5 C6 C7 -1.9(13) . . . . ? C5 C6 C7 C8 1.8(12) . . . . ? C6 C7 C8 C3 -0.9(12) . . . . ? C6 C7 C8 C1 -179.0(8) . . . . ? C4 C3 C8 C7 0.1(11) . . . . ? C2 C3 C8 C7 177.9(7) . . . . ? C4 C3 C8 C1 178.6(7) . . . . ? C2 C3 C8 C1 -3.7(8) . . . . ? O1 C1 C8 C7 0.2(14) . . . . ? N1 C1 C8 C7 179.7(7) . . . . ? O1 C1 C8 C3 -178.1(8) . . . . ? N1 C1 C8 C3 1.5(8) . . . . ? C1 N1 C9 C14 108.3(8) . . . . ? C2 N1 C9 C14 -83.2(8) . . . . ? C1 N1 C9 C10 -74.9(9) . . . . ? C2 N1 C9 C10 93.6(8) . . . . ? C14 C9 C10 C11 -1.6(10) . . . . ? N1 C9 C10 C11 -178.3(6) . . . . ? C14 C9 C10 C15 177.8(7) . . . . ? N1 C9 C10 C15 1.1(10) . . . . ? C9 C10 C11 C12 1.5(11) . . . . ? C15 C10 C11 C12 -177.9(7) . . . . ? C10 C11 C12 C13 -1.0(12) . . . . ? C11 C12 C13 C14 0.6(12) . . . . ? C10 C9 C14 C13 1.3(11) . . . . ? N1 C9 C14 C13 178.1(7) . . . . ? C12 C13 C14 C9 -0.8(12) . . . . ? C11 C10 C15 O2 168.8(8) . . . . ? C9 C10 C15 O2 -10.5(12) . . . . ? C11 C10 C15 O3 -8.0(10) . . . . ? C9 C10 C15 O3 172.6(7) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A C14 H14 O1 0.93 2.66 3.445(10) 142.6 1_455 C5 H5 O2 0.93 2.53 3.358(10) 149.0 4_466 C7 H7 O3 0.93 2.51 3.302(10) 143.8 3_745 O3 H3 O1 0.91(2) 1.69(3) 2.590(8) 171(9) 3_755 _diffrn_measured_fraction_theta_max 0.966 _diffrn_reflns_theta_full 25.05 _diffrn_measured_fraction_theta_full 0.966 _refine_diff_density_max 0.164 _refine_diff_density_min -0.174 _refine_diff_density_rms 0.045