# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 #TrackingRef 'Cincic et al_ccdc_deposit.cif' #=================================================================== _audit_creation_method SHELXL-97 #=================================================================== # 1. SUBMISSION DETAILS _publ_contact_author_name 'Dr Dominik Cincic' _publ_contact_author_address ; Department of Chemistry, Laboratory of General and Inorganic Chemistry Faculty of Science, University of Zagreb, HR-10000 Zagreb, Horvatovac 102a, Croatia ; _publ_contact_author_phone '385 1 4606 362' _publ_contact_author_fax '385 1 4606 341' _publ_contact_author_email dominik@chem.pmf.hr _publ_requested_category ? _publ_requested_coeditor_name ? _publ_contact_letter ; August 28, 2012. Dear Madam/Dear Sir, This CIF file contains the results of the collection, reduction, and X-ray structural data of two organic compounds. The structures have been described in the manuscript under the title: The role of humidity and solvent vapour in the solid-state synthesis of Schiff bases via vapour digestion and ball milling by the authors: D. Cincic, I. Brekalo and B. Kaitner. The manuscript will be sent to Chem. Commun. for publication upon the deposition of the data with the CCDC and the availability of the the deposition numbers. The data were checked using checkCIF/PLATON. We ask you kindly that the structural data for both molecules be deposited with CCDC. Sincerely yours, D. Cincic, I. Brekalo and B. Kaitner. ; _publ_author_name D.Cincic #===================================================================== data_01 _database_code_depnum_ccdc_archive 'CCDC 898504' #TrackingRef 'Cincic et al_ccdc_deposit.cif' #===================================================================== _chemical_name_systematic ; 1-[(4-hydroxy-carboxyphenylamino)methylene]naphthalene-2(1H)-one ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H13 N O4' _chemical_formula_sum 'C18 H13 N O4' _chemical_formula_weight 307.29 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/n' _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 10.4331(5) _cell_length_b 11.4045(5) _cell_length_c 11.4271(6) _cell_angle_alpha 90.00 _cell_angle_beta 97.021(4) _cell_angle_gamma 90.00 _cell_volume 1349.45(11) _cell_formula_units_Z 4 _cell_measurement_temperature 295 _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.513 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 640 _exptl_absorpt_coefficient_mu 0.108 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 295 _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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7453 _diffrn_reflns_av_R_equivalents 0.0451 _diffrn_reflns_av_sigmaI/netI 0.0516 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 4.27 _diffrn_reflns_theta_max 27.00 _reflns_number_total 2910 _reflns_number_gt 2006 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _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^)+(0.0774P)^2^+0.0000P] 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 2910 _refine_ls_number_parameters 214 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0863 _refine_ls_R_factor_gt 0.0549 _refine_ls_wR_factor_ref 0.1459 _refine_ls_wR_factor_gt 0.1279 _refine_ls_goodness_of_fit_ref 1.017 _refine_ls_restrained_S_all 1.017 _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 -0.22042(14) 1.37744(12) 0.33717(13) 0.0349(4) Uani 1 1 d . . . O2 O -0.27246(13) 1.18696(12) 0.32841(13) 0.0327(4) Uani 1 1 d . . . O3 O -0.00841(15) 1.44670(11) 0.26500(14) 0.0348(4) Uani 1 1 d . . . H3A H -0.0741 1.4531 0.2973 0.052 Uiso 1 1 calc R . . O4 O -0.01807(14) 0.77862(12) 0.12398(13) 0.0347(4) Uani 1 1 d . . . N1 N 0.07195(16) 0.98619(15) 0.13582(15) 0.0260(4) Uani 1 1 d . . . C1 C -0.07879(19) 1.24480(16) 0.25712(17) 0.0234(4) Uani 1 1 d . . . C2 C 0.00896(19) 1.33311(16) 0.23742(17) 0.0263(5) Uani 1 1 d . . . C3 C 0.1194(2) 1.30518(17) 0.18517(18) 0.0302(5) Uani 1 1 d . . . H3 H 0.1778 1.3640 0.1720 0.036 Uiso 1 1 calc R . . C4 C 0.14269(19) 1.19225(17) 0.15312(18) 0.0288(5) Uani 1 1 d . . . H4 H 0.2172 1.1745 0.1196 0.035 Uiso 1 1 calc R . . C5 C 0.05458(18) 1.10347(16) 0.17074(16) 0.0239(4) Uani 1 1 d . . . C6 C -0.05489(18) 1.13038(16) 0.22262(16) 0.0238(4) Uani 1 1 d . . . H6 H -0.1133 1.0713 0.2346 0.029 Uiso 1 1 calc R . . C7 C -0.1967(2) 1.27581(17) 0.31155(17) 0.0265(5) Uani 1 1 d . . . C8 C 0.08442(19) 0.74246(17) 0.08292(17) 0.0258(5) Uani 1 1 d . . . C9 C 0.18167(18) 0.82421(16) 0.05801(16) 0.0225(4) Uani 1 1 d . . . C10 C 0.29374(18) 0.78228(16) 0.00524(16) 0.0233(4) Uani 1 1 d . . . C11 C 0.39000(19) 0.85633(17) -0.03004(17) 0.0276(5) Uani 1 1 d . . . H11 H 0.3835 0.9369 -0.0198 0.033 Uiso 1 1 calc R . . C12 C 0.49369(19) 0.81153(18) -0.07953(18) 0.0299(5) Uani 1 1 d . . . H12 H 0.5557 0.8623 -0.1026 0.036 Uiso 1 1 calc R . . C13 C 0.5069(2) 0.69181(18) -0.09549(18) 0.0315(5) Uani 1 1 d . . . H13 H 0.5784 0.6622 -0.1269 0.038 Uiso 1 1 calc R . . C14 C 0.4133(2) 0.61773(17) -0.06443(18) 0.0300(5) Uani 1 1 d . . . H14 H 0.4208 0.5376 -0.0769 0.036 Uiso 1 1 calc R . . C15 C 0.30641(19) 0.66061(16) -0.01417(17) 0.0256(5) Uani 1 1 d . . . C16 C 0.2086(2) 0.58277(17) 0.01655(18) 0.0311(5) Uani 1 1 d . . . H16 H 0.2179 0.5028 0.0042 0.037 Uiso 1 1 calc R . . C17 C 0.1035(2) 0.62095(17) 0.06278(19) 0.0311(5) Uani 1 1 d . . . H17 H 0.0424 0.5671 0.0818 0.037 Uiso 1 1 calc R . . C18 C 0.16974(18) 0.94221(17) 0.08682(17) 0.0258(5) Uani 1 1 d . . . H18 H 0.2348 0.9932 0.0705 0.031 Uiso 1 1 calc R . . H1A H 0.010(2) 0.927(2) 0.144(2) 0.044(7) Uiso 1 1 d . . . H2A H -0.3569 1.2205 0.3471 0.063(8) 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 O1 0.0334(9) 0.0294(9) 0.0433(9) -0.0038(7) 0.0103(7) 0.0063(6) O2 0.0245(8) 0.0312(8) 0.0443(9) -0.0010(7) 0.0121(6) 0.0038(6) O3 0.0392(9) 0.0235(8) 0.0442(10) -0.0019(7) 0.0152(7) 0.0005(6) O4 0.0295(8) 0.0365(9) 0.0411(9) -0.0053(7) 0.0157(7) -0.0066(6) N1 0.0243(9) 0.0253(9) 0.0290(9) -0.0032(7) 0.0053(7) 0.0000(7) C1 0.0221(10) 0.0267(11) 0.0213(10) -0.0003(8) 0.0022(7) 0.0033(8) C2 0.0307(11) 0.0228(10) 0.0255(10) -0.0010(8) 0.0036(8) 0.0017(8) C3 0.0275(11) 0.0271(11) 0.0366(12) 0.0021(9) 0.0063(9) -0.0038(9) C4 0.0222(10) 0.0318(12) 0.0329(11) -0.0015(9) 0.0054(8) 0.0024(8) C5 0.0240(10) 0.0263(11) 0.0213(10) 0.0001(8) 0.0024(7) 0.0018(8) C6 0.0231(10) 0.0244(11) 0.0244(10) 0.0001(8) 0.0039(8) -0.0004(8) C7 0.0268(11) 0.0275(12) 0.0251(10) 0.0019(9) 0.0029(8) 0.0011(8) C8 0.0253(11) 0.0312(11) 0.0215(10) -0.0013(8) 0.0050(8) -0.0023(8) C9 0.0215(10) 0.0234(10) 0.0225(10) 0.0011(8) 0.0020(7) -0.0003(8) C10 0.0225(10) 0.0278(11) 0.0194(9) -0.0007(8) 0.0013(7) 0.0017(8) C11 0.0283(11) 0.0244(11) 0.0306(11) -0.0003(9) 0.0058(8) 0.0010(8) C12 0.0247(11) 0.0325(12) 0.0332(11) 0.0008(9) 0.0071(8) 0.0022(9) C13 0.0270(11) 0.0364(12) 0.0315(11) -0.0021(9) 0.0053(8) 0.0113(9) C14 0.0325(12) 0.0250(11) 0.0315(11) -0.0013(9) 0.0006(9) 0.0090(9) C15 0.0280(11) 0.0239(10) 0.0240(10) 0.0018(8) -0.0004(8) 0.0010(8) C16 0.0352(12) 0.0236(11) 0.0337(12) -0.0017(9) 0.0015(9) -0.0005(9) C17 0.0328(12) 0.0251(11) 0.0359(12) 0.0017(9) 0.0060(9) -0.0084(9) C18 0.0221(10) 0.0286(11) 0.0268(10) 0.0017(9) 0.0037(8) -0.0010(8) _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 C7 1.228(2) . ? O2 C7 1.314(2) . ? O3 C2 1.351(2) . ? O4 C8 1.287(2) . ? N1 C18 1.321(3) . ? N1 C5 1.414(2) . ? C1 C6 1.394(3) . ? C1 C2 1.398(3) . ? C1 C7 1.488(3) . ? C2 C3 1.398(3) . ? C3 C4 1.369(3) . ? C4 C5 1.399(3) . ? C5 C6 1.384(3) . ? C8 C17 1.423(3) . ? C8 C9 1.432(3) . ? C9 C18 1.395(3) . ? C9 C10 1.460(3) . ? C10 C11 1.408(3) . ? C10 C15 1.414(3) . ? C11 C12 1.379(3) . ? C12 C13 1.386(3) . ? C13 C14 1.371(3) . ? C14 C15 1.403(3) . ? C15 C16 1.428(3) . ? C16 C17 1.347(3) . ? 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 C18 N1 C5 127.66(18) . . ? C6 C1 C2 119.04(18) . . ? C6 C1 C7 121.76(18) . . ? C2 C1 C7 119.18(17) . . ? O3 C2 C1 122.98(18) . . ? O3 C2 C3 117.34(17) . . ? C1 C2 C3 119.67(18) . . ? C4 C3 C2 120.73(18) . . ? C3 C4 C5 120.10(19) . . ? C6 C5 C4 119.50(17) . . ? C6 C5 N1 118.14(17) . . ? C4 C5 N1 122.35(17) . . ? C5 C6 C1 120.94(18) . . ? O1 C7 O2 123.43(19) . . ? O1 C7 C1 121.67(18) . . ? O2 C7 C1 114.90(17) . . ? O4 C8 C17 120.67(18) . . ? O4 C8 C9 120.28(17) . . ? C17 C8 C9 119.05(18) . . ? C18 C9 C8 119.71(18) . . ? C18 C9 C10 120.84(17) . . ? C8 C9 C10 119.44(17) . . ? C11 C10 C15 117.39(17) . . ? C11 C10 C9 123.84(17) . . ? C15 C10 C9 118.76(17) . . ? C12 C11 C10 121.19(18) . . ? C11 C12 C13 120.97(19) . . ? C14 C13 C12 119.17(18) . . ? C13 C14 C15 121.22(18) . . ? C14 C15 C10 120.03(18) . . ? C14 C15 C16 120.75(18) . . ? C10 C15 C16 119.22(18) . . ? C17 C16 C15 122.41(19) . . ? C16 C17 C8 121.01(19) . . ? N1 C18 C9 124.21(18) . . ? _diffrn_measured_fraction_theta_max 0.983 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.983 _refine_diff_density_max 0.289 _refine_diff_density_min -0.230 _refine_diff_density_rms 0.056 #===================================================================== data_02 _database_code_depnum_ccdc_archive 'CCDC 898505' #TrackingRef 'Cincic et al_ccdc_deposit.cif' #===================================================================== _chemical_name_systematic ; 2-hydroxy-5-[N-(4-hydroxy-3-methoxybenzylidene)]aminobenzoate monohydrate ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C15 H13 N O5,H2 O' _chemical_formula_sum 'C15 H15 N O6' _chemical_formula_weight 305.28 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/n' _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 11.0959(6) _cell_length_b 8.3683(4) _cell_length_c 14.7951(8) _cell_angle_alpha 90.00 _cell_angle_beta 100.062(5) _cell_angle_gamma 90.00 _cell_volume 1352.65(12) _cell_formula_units_Z 4 _cell_measurement_temperature 295 _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.17 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.499 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 640 _exptl_absorpt_coefficient_mu 0.117 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 295 _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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7332 _diffrn_reflns_av_R_equivalents 0.0267 _diffrn_reflns_av_sigmaI/netI 0.0531 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 4.25 _diffrn_reflns_theta_max 27.00 _reflns_number_total 2932 _reflns_number_gt 1847 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _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^)+(0.0564P)^2^+0.0000P] 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 2932 _refine_ls_number_parameters 214 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0687 _refine_ls_R_factor_gt 0.0408 _refine_ls_wR_factor_ref 0.1007 _refine_ls_wR_factor_gt 0.0953 _refine_ls_goodness_of_fit_ref 0.889 _refine_ls_restrained_S_all 0.889 _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 0.29785(11) 0.96231(14) 0.07450(8) 0.0293(3) Uani 1 1 d . . . O2 O 0.23604(11) 1.13642(13) 0.17140(8) 0.0271(3) Uani 1 1 d . . . O3 O 0.21236(12) 0.97014(15) -0.09299(9) 0.0322(3) Uani 1 1 d . . . O4 O -0.50650(13) 1.83932(15) 0.17453(9) 0.0350(3) Uani 1 1 d . . . O5 O -0.52698(11) 1.78035(15) -0.00891(8) 0.0305(3) Uani 1 1 d . . . N1 N -0.14568(13) 1.38984(16) -0.01691(10) 0.0223(3) Uani 1 1 d . . . C1 C 0.13082(15) 1.12870(18) 0.01722(11) 0.0195(4) Uani 1 1 d . . . C2 C 0.12886(16) 1.07529(19) -0.07279(11) 0.0231(4) Uani 1 1 d . . . C3 C 0.03778(17) 1.1311(2) -0.14304(12) 0.0265(4) Uani 1 1 d . . . H3 H 0.0365 1.0977 -0.2031 0.032 Uiso 1 1 calc R . . C4 C -0.05025(16) 1.23556(19) -0.12348(11) 0.0248(4) Uani 1 1 d . . . H4 H -0.1102 1.2730 -0.1706 0.030 Uiso 1 1 calc R . . C5 C -0.04997(16) 1.28527(18) -0.03395(11) 0.0209(4) Uani 1 1 d . . . C6 C 0.04109(15) 1.23281(18) 0.03564(11) 0.0205(4) Uani 1 1 d . . . H6 H 0.0421 1.2678 0.0954 0.025 Uiso 1 1 calc R . . C7 C 0.22825(15) 1.07301(19) 0.09434(11) 0.0221(4) Uani 1 1 d . . . C8 C -0.43329(16) 1.70802(19) 0.04827(11) 0.0226(4) Uani 1 1 d . . . C9 C -0.42807(16) 1.74141(19) 0.14261(12) 0.0252(4) Uani 1 1 d . . . C10 C -0.33729(17) 1.6702(2) 0.20613(12) 0.0266(4) Uani 1 1 d . . . H10 H -0.3334 1.6913 0.2683 0.032 Uiso 1 1 calc R . . C11 C -0.25311(16) 1.5692(2) 0.17889(11) 0.0269(4) Uani 1 1 d . . . H11 H -0.1934 1.5219 0.2226 0.032 Uiso 1 1 calc R . . C12 C -0.25659(16) 1.53696(19) 0.08601(11) 0.0231(4) Uani 1 1 d . . . C13 C -0.34905(15) 1.60736(19) 0.02042(11) 0.0226(4) Uani 1 1 d . . . H13 H -0.3529 1.5856 -0.0417 0.027 Uiso 1 1 calc R . . C14 C -0.16510(16) 1.43154(19) 0.06387(12) 0.0244(4) Uani 1 1 d . . . H14 H -0.1128 1.3871 0.1135 0.029 Uiso 1 1 calc R . . C15 C -0.53252(17) 1.7575(2) -0.10545(11) 0.0291(4) Uani 1 1 d . . . H15B H -0.4591 1.7981 -0.1231 0.044 Uiso 1 1 calc R . . H15A H -0.6020 1.8136 -0.1385 0.044 Uiso 1 1 calc R . . H15C H -0.5402 1.6456 -0.1195 0.044 Uiso 1 1 calc R . . H4A H -0.576(3) 1.880(3) 0.1316(18) 0.087(9) Uiso 1 1 d . . . H3A H 0.261(2) 0.948(3) -0.0327(17) 0.068(7) Uiso 1 1 d . . . H1A H -0.1969(17) 1.435(2) -0.0736(12) 0.033(5) Uiso 1 1 d . . . O6 O 0.23742(14) 0.96596(14) 0.32658(8) 0.0389(4) Uani 1 1 d . . . H6A H 0.2511 0.8510 0.3221 0.079(8) Uiso 1 1 d . . . H6B H 0.2391 1.0102 0.2607 0.081(8) 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 O1 0.0232(7) 0.0313(7) 0.0306(7) -0.0050(6) -0.0031(5) 0.0100(6) O2 0.0322(8) 0.0263(6) 0.0208(6) 0.0012(5) -0.0009(5) 0.0042(5) O3 0.0295(8) 0.0388(7) 0.0273(7) -0.0077(6) 0.0023(6) 0.0114(6) O4 0.0329(8) 0.0393(8) 0.0309(7) -0.0056(6) 0.0004(6) 0.0154(6) O5 0.0271(8) 0.0380(7) 0.0242(6) 0.0001(6) -0.0013(5) 0.0098(6) N1 0.0206(8) 0.0223(7) 0.0230(8) 0.0028(7) 0.0009(6) 0.0024(6) C1 0.0184(9) 0.0183(8) 0.0213(8) 0.0015(7) 0.0019(6) -0.0023(7) C2 0.0222(10) 0.0226(9) 0.0243(9) 0.0008(8) 0.0036(7) 0.0004(7) C3 0.0310(11) 0.0285(9) 0.0193(9) -0.0026(8) 0.0026(7) 0.0014(8) C4 0.0238(10) 0.0272(9) 0.0215(9) 0.0026(8) -0.0018(7) 0.0010(7) C5 0.0194(9) 0.0176(8) 0.0253(9) 0.0011(7) 0.0030(7) -0.0002(7) C6 0.0224(10) 0.0190(8) 0.0197(8) -0.0005(7) 0.0025(7) -0.0012(7) C7 0.0197(10) 0.0217(9) 0.0243(9) 0.0026(8) 0.0020(7) -0.0018(7) C8 0.0202(10) 0.0216(9) 0.0243(9) 0.0025(8) -0.0012(7) 0.0012(7) C9 0.0246(10) 0.0229(9) 0.0278(9) -0.0007(8) 0.0034(7) 0.0020(7) C10 0.0312(11) 0.0281(9) 0.0191(9) -0.0019(8) 0.0007(7) 0.0032(8) C11 0.0258(10) 0.0271(9) 0.0251(9) 0.0025(8) -0.0028(7) 0.0040(8) C12 0.0222(10) 0.0203(9) 0.0262(9) 0.0017(8) 0.0025(7) 0.0006(7) C13 0.0237(10) 0.0235(9) 0.0199(9) -0.0001(7) 0.0021(7) -0.0013(7) C14 0.0225(10) 0.0221(9) 0.0270(9) 0.0048(8) 0.0001(7) -0.0007(7) C15 0.0252(11) 0.0372(11) 0.0232(9) 0.0031(8) -0.0004(7) 0.0033(8) O6 0.0630(10) 0.0294(7) 0.0212(7) 0.0002(6) -0.0016(6) -0.0116(7) _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 C7 1.2728(19) . ? O2 C7 1.2468(19) . ? O3 C2 1.349(2) . ? O4 C9 1.340(2) . ? O5 C8 1.3621(19) . ? O5 C15 1.4316(19) . ? N1 C14 1.299(2) . ? N1 C5 1.432(2) . ? C1 C6 1.385(2) . ? C1 C2 1.401(2) . ? C1 C7 1.502(2) . ? C2 C3 1.397(2) . ? C3 C4 1.379(2) . ? C4 C5 1.388(2) . ? C5 C6 1.382(2) . ? C8 C13 1.374(2) . ? C8 C9 1.415(2) . ? C9 C10 1.386(2) . ? C10 C11 1.372(2) . ? C11 C12 1.394(2) . ? C12 C13 1.412(2) . ? C12 C14 1.426(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 C8 O5 C15 117.09(13) . . ? C14 N1 C5 125.01(15) . . ? C6 C1 C2 119.68(15) . . ? C6 C1 C7 119.49(15) . . ? C2 C1 C7 120.83(15) . . ? O3 C2 C3 119.27(15) . . ? O3 C2 C1 121.43(15) . . ? C3 C2 C1 119.29(15) . . ? C4 C3 C2 120.18(15) . . ? C3 C4 C5 120.45(16) . . ? C6 C5 C4 119.69(16) . . ? C6 C5 N1 122.07(15) . . ? C4 C5 N1 118.24(15) . . ? C5 C6 C1 120.67(15) . . ? O2 C7 O1 124.94(15) . . ? O2 C7 C1 119.23(14) . . ? O1 C7 C1 115.83(14) . . ? O5 C8 C13 124.87(15) . . ? O5 C8 C9 114.85(15) . . ? C13 C8 C9 120.28(15) . . ? O4 C9 C10 117.62(16) . . ? O4 C9 C8 123.46(16) . . ? C10 C9 C8 118.92(16) . . ? C11 C10 C9 121.14(16) . . ? C10 C11 C12 120.38(16) . . ? C11 C12 C13 119.24(15) . . ? C11 C12 C14 116.61(15) . . ? C13 C12 C14 124.14(15) . . ? C8 C13 C12 120.03(15) . . ? N1 C14 C12 128.11(16) . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.373 _refine_diff_density_min -0.201 _refine_diff_density_rms 0.047