# Supplementary Material (ESI) for ChemComm # This journal is © The Royal Society of Chemistry 2000 # CCDC Number: 182/1801 data_General _audit_creation_date 'Wed Jul 5 13:10:18 2000' _audit_creation_method 'by teXsan' _audit_update_record ? #------------------------------------------------------------------------------ # PROCESSING SUMMARY (IUCr Office Use Only) _journal_date_recd_electronic ? _journal_date_from_coeditor ? _journal_date_accepted ? _journal_coeditor_code ? #------------------------------------------------------------------------------ # SUBMISSION DETAILS _publ_contact_author_name ' Kazuhisa Hiratani ' _publ_contact_author_address ; 1-1-4 Higashi, Tsukuba, Ibaraki 305-8562, Japan ; _publ_contact_author_email ' hiratani@nair.go.jp ' _publ_contact_author_fax ' 81-298-61-3029 ' _publ_contact_author_phone ' 81-298-61-3021 ' _publ_requested_journal ' Chemical Communications ' _publ_requested_category ' CHOOSE FI FM FO CI CM CO or AD' _publ_requested_coeditor_name ? #------------------------------------------------------------------------------ # TITLE AND AUTHOR LIST _publ_section_title ; Highly selective formation of 2:2 macrocycles from a novel hydroxybenzaldehyde derivative and diamines ; _publ_section_title_footnote ; ENTER FOOTNOTE TO TITLE OF PAPER ; loop_ _publ_author_name _publ_author_footnote _publ_author_address ' Hirohiko Houjou ' ; FIRST AUTHORS FOOTNOTES ; ; 1-1-4 Higashi, Tsukuba, Ibaraki 305-8562, Japan ; _publ_section_synopsis ; ENTER SYNOPSIS ; #------------------------------------------------------------------------------ # TEXT _publ_section_abstract ; A hydroxybenzaldehyde derivative which has isobutenyl linkage reacts with a variety of diamines to efficiently result in 2:2 macrocyclic compound. ; _publ_section_comment ; ENTER TEXT ; _publ_section_acknowledgements ; ENTER ACKNOWLEDGEMENTS ; _publ_section_references ; ENTER OTHER REFERENCES Molecular Structure Corporation, Rigaku Corporation. (1999). teXsan. Single Crystal Structure Analysis Software. Version 1.10. MSC, 3200 Research Forest Drive, The Woodlands, TX 77381, USA. Rigaku, 3-9-12 Akishima, Tokyo, Japan. ; _publ_section_figure_captions ; X-ray crystal structures of (a)1 and (b)2. ; _publ_section_exptl_prep ; ENTER COMPOUND PREPARATION DETAILS ; _publ_section_exptl_refinement ; ENTER SPECIAL DETAILS OF THE REFINEMENT ; #------------------------------------------------------------------------------ data_aloh #------------------------------------------------------------------------------ # CHEMICAL DATA _chemical_formula_sum 'C18 H16 O4 ' _chemical_formula_moiety 'C18 H16 O4 ' _chemical_formula_weight 296.32 _chemical_melting_point ? #------------------------------------------------------------------------------ # CRYSTAL DATA _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/a 1' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_as_xyz x,y,z 1/2-x,1/2+y,-z -x,-y,-z 1/2+x,1/2-y,z _cell_length_a 7.9346(4) _cell_length_b 14.3035(8) _cell_length_c 13.3949(7) _cell_angle_alpha 90 _cell_angle_beta 102.181(2) _cell_angle_gamma 90 _cell_volume 1486.0(1) _cell_formula_units_Z 4 _cell_measurement_reflns_used 11568 _cell_measurement_theta_min 2.1 _cell_measurement_theta_max 27.5 _cell_measurement_temperature 193.2 #------------------------------------------------------------------------------ _exptl_crystal_description 'prism' _exptl_crystal_colour 'colorless' _exptl_crystal_size_max 1.200 _exptl_crystal_size_mid 0.500 _exptl_crystal_size_min 0.400 _exptl_crystal_size_rad ? _exptl_crystal_density_diffrn 1.324 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_absorpt_coefficient_mu 0.093 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(Higashi, 1995)' _exptl_absorpt_correction_T_min 0.891 _exptl_absorpt_correction_T_max 0.963 #------------------------------------------------------------------------------ # EXPERIMENTAL DATA _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.7107 _diffrn_measurement_device_type 'Rigaku RAXIS-RAPID Imaging Plate' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 3555 _diffrn_reflns_av_R_equivalents 0.021 _diffrn_reflns_theta_max 27.48 _diffrn_measured_fraction_theta_max 0.9988 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.9988 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 #------------------------------------------------------------------------------ # REFINEMENT DATA _refine_special_details ; Refinement using reflections with F^2^ > 1.5 sigma(F^2^). The weighted R-factor (wR) and goodness of fit (S) are based on F^2^. R-factor (gt) are based on F. The threshold expression of F^2^ > 2.0 sigma(F^2^) is used only for calculating R-factor (gt). ; _reflns_number_total 3410 _reflns_number_gt 2882 _reflns_threshold_expression F^2^>2.0\s(F^2^) _refine_ls_structure_factor_coef Fsqd _refine_ls_R_factor_gt 0.0400 _refine_ls_wR_factor_ref 0.0779 _refine_ls_hydrogen_treatment refxyz _refine_ls_number_reflns 2967 _refine_ls_number_parameters 247 _refine_ls_goodness_of_fit_ref 3.547 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^) + (0.00800(Max(Fo^2^,0) + 2Fc^2^)/3)^2^]' _refine_ls_shift/su_max 0.0005 _refine_diff_density_max 0.25 _refine_diff_density_min -0.27 _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details ? _refine_ls_abs_structure_Flack ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.003 0.002 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; 'H' 'H' 0.000 0.000 ;International Tables for Crystallography (1992, Vol. C, Table 6.1.1.2) ; 'O' 'O' 0.011 0.006 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; #------------------------------------------------------------------------------ # ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O(1) O 1.0498(1) 0.53557(7) 0.25546(7) 0.0363(3) Uani 1.00 d . . . O(2) O 1.2710(1) 0.67767(7) 0.27887(9) 0.0499(3) Uani 1.00 d . . . O(3) O 0.6494(1) 0.17483(6) 0.29315(7) 0.0291(2) Uani 1.00 d . . . O(4) O 0.8204(1) 0.04576(6) 0.41682(8) 0.0433(3) Uani 1.00 d . . . C(1) C 0.8504(1) 0.52589(8) 0.09832(9) 0.0266(3) Uani 1.00 d . . . C(2) C 0.9879(2) 0.57233(8) 0.16176(9) 0.0261(3) Uani 1.00 d . . . C(3) C 1.0582(1) 0.65391(8) 0.12765(10) 0.0288(3) Uani 1.00 d . . . C(4) C 0.9899(2) 0.68872(9) 0.0293(1) 0.0356(4) Uani 1.00 d . . . C(5) C 0.8549(2) 0.6438(1) -0.0331(1) 0.0390(4) Uani 1.00 d . . . C(6) C 0.7875(2) 0.5629(1) 0.0022(1) 0.0339(3) Uani 1.00 d . . . C(7) C 1.2019(2) 0.70250(10) 0.1924(1) 0.0385(4) Uani 1.00 d . . . C(8) C 0.7762(2) 0.43797(9) 0.1344(1) 0.0290(3) Uani 1.00 d . . . C(9) C 0.6373(1) 0.45225(8) 0.19508(9) 0.0250(3) Uani 1.00 d . . . C(10) C 0.5651(2) 0.53370(10) 0.2069(1) 0.0379(4) Uani 1.00 d . . . C(11) C 0.5841(2) 0.36367(9) 0.24218(10) 0.0272(3) Uani 1.00 d . . . C(12) C 0.7118(1) 0.33312(8) 0.33760(9) 0.0231(3) Uani 1.00 d . . . C(13) C 0.8003(2) 0.39758(9) 0.40679(10) 0.0294(3) Uani 1.00 d . . . C(14) C 0.9147(2) 0.37029(10) 0.4961(1) 0.0334(3) Uani 1.00 d . . . C(15) C 0.9417(2) 0.27660(9) 0.5165(1) 0.0313(3) Uani 1.00 d . . . C(16) C 0.8555(1) 0.20902(8) 0.44922(9) 0.0260(3) Uani 1.00 d . . . C(17) C 0.7387(1) 0.23775(8) 0.36000(9) 0.0225(3) Uani 1.00 d . . . C(18) C 0.8885(2) 0.11039(10) 0.4712(1) 0.0353(4) Uani 1.00 d . . . H(1) H 1.042(2) 0.746(1) 0.007(1) 0.0461 Uiso 1.00 calc . . . H(2) H 0.807(2) 0.667(1) -0.101(1) 0.0461 Uiso 1.00 calc . . . H(3) H 0.695(2) 0.529(1) -0.040(1) 0.0461 Uiso 1.00 calc . . . H(4) H 1.245(2) 0.763(1) 0.160(1) 0.0461 Uiso 1.00 calc . . . H(5) H 0.872(2) 0.4009(9) 0.177(1) 0.0380 Uiso 1.00 calc . . . H(6) H 0.727(2) 0.399(1) 0.074(1) 0.0461 Uiso 1.00 calc . . . H(7) H 0.596(2) 0.5883(10) 0.174(1) 0.0380 Uiso 1.00 calc . . . H(8) H 0.475(2) 0.5404(9) 0.248(1) 0.0380 Uiso 1.00 calc . . . H(9) H 0.471(2) 0.3736(10) 0.262(1) 0.0461 Uiso 1.00 calc . . . H(10) H 0.575(2) 0.3130(10) 0.193(1) 0.0380 Uiso 1.00 calc . . . H(11) H 0.784(2) 0.4648(10) 0.394(1) 0.0380 Uiso 1.00 calc . . . H(12) H 0.968(2) 0.416(1) 0.540(1) 0.0461 Uiso 1.00 calc . . . H(13) H 1.018(2) 0.2557(10) 0.576(1) 0.0380 Uiso 1.00 calc . . . H(14) H 0.971(2) 0.0981(9) 0.535(1) 0.0380 Uiso 1.00 calc . . . H(15) H 1.129(2) 0.573(1) 0.283(1) 0.0461 Uiso 1.00 calc . . . H(16) H 0.678(2) 0.118(1) 0.322(1) 0.0461 Uiso 1.00 calc . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 O(1) 0.0385(5) 0.0359(5) 0.0299(5) -0.0031(4) -0.0035(4) 0.0046(4) O(2) 0.0396(6) 0.0486(6) 0.0552(7) -0.0039(5) -0.0040(5) -0.0117(5) O(3) 0.0308(4) 0.0227(4) 0.0313(5) -0.0034(4) 0.0009(4) -0.0008(4) O(4) 0.0457(6) 0.0279(5) 0.0519(6) 0.0005(4) 0.0005(5) 0.0051(5) C(1) 0.0248(6) 0.0294(6) 0.0269(6) 0.0012(5) 0.0082(5) -0.0003(5) C(2) 0.0255(6) 0.0277(6) 0.0256(6) 0.0044(5) 0.0067(5) 0.0022(5) C(3) 0.0255(6) 0.0267(6) 0.0361(7) 0.0024(5) 0.0107(5) -0.0004(5) C(4) 0.0370(7) 0.0331(7) 0.0410(8) 0.0035(6) 0.0181(6) 0.0101(6) C(5) 0.0397(8) 0.0499(9) 0.0282(7) 0.0057(7) 0.0086(6) 0.0126(6) C(6) 0.0304(7) 0.0438(7) 0.0267(6) -0.0006(6) 0.0042(6) -0.0001(6) C(7) 0.0298(7) 0.0309(7) 0.0559(9) 0.0001(6) 0.0116(7) -0.0064(7) C(8) 0.0287(6) 0.0269(6) 0.0317(7) -0.0014(5) 0.0072(5) -0.0010(5) C(9) 0.0218(5) 0.0267(6) 0.0249(6) -0.0007(5) 0.0017(5) 0.0021(5) C(10) 0.0382(7) 0.0300(7) 0.0490(9) 0.0058(6) 0.0170(7) 0.0073(6) C(11) 0.0244(6) 0.0276(6) 0.0281(7) -0.0035(5) 0.0023(5) 0.0016(5) C(12) 0.0207(5) 0.0260(6) 0.0234(6) -0.0010(5) 0.0062(5) 0.0012(5) C(13) 0.0327(6) 0.0244(6) 0.0304(7) -0.0007(5) 0.0050(5) -0.0020(5) C(14) 0.0355(7) 0.0345(7) 0.0276(7) -0.0039(6) 0.0010(6) -0.0074(5) C(15) 0.0277(6) 0.0404(7) 0.0242(6) 0.0026(6) 0.0019(5) 0.0005(6) C(16) 0.0237(6) 0.0298(6) 0.0253(6) 0.0018(5) 0.0073(5) 0.0023(5) C(17) 0.0203(5) 0.0254(6) 0.0230(6) -0.0020(4) 0.0070(5) -0.0019(5) C(18) 0.0330(7) 0.0358(7) 0.0353(7) 0.0040(6) 0.0033(6) 0.0073(6) #------------------------------------------------------------------------------ _computing_data_collection 'PROCESS-AUTO' _computing_cell_refinement 'PROCESS-AUTO' _computing_data_reduction 'teXsan Ver. 1.10' _computing_structure_solution SIR92 _computing_structure_refinement 'teXsan Ver. 1.10' _computing_publication_material 'teXsan Ver. 1.10' _computing_molecular_graphics ? #------------------------------------------------------------------------------ _geom_special_details ; ? ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag O(1) C(2) 1.354(1) . . yes O(2) C(7) 1.225(2) . . yes O(3) C(17) 1.359(1) . . yes O(4) C(18) 1.229(2) . . yes C(1) C(2) 1.401(2) . . yes C(1) C(6) 1.384(2) . . yes C(1) C(8) 1.511(2) . . yes C(2) C(3) 1.410(2) . . yes C(3) C(4) 1.406(2) . . yes C(3) C(7) 1.456(2) . . yes C(4) C(5) 1.371(2) . . yes C(5) C(6) 1.398(2) . . yes C(8) C(9) 1.515(2) . . yes C(9) C(10) 1.322(2) . . yes C(9) C(11) 1.515(2) . . yes C(11) C(12) 1.518(2) . . yes C(12) C(13) 1.388(2) . . yes C(12) C(17) 1.403(2) . . yes C(13) C(14) 1.396(2) . . yes C(14) C(15) 1.375(2) . . yes C(15) C(16) 1.398(2) . . yes C(16) C(17) 1.410(2) . . yes C(16) C(18) 1.454(2) . . yes #------------------------------------------------------------------------------ loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C(2) C(1) C(6) 117.7(1) . 1_555 1_555 yes C(2) C(1) C(8) 120.5(1) . 1_555 1_555 yes C(6) C(1) C(8) 121.9(1) . 1_555 1_555 yes O(1) C(2) C(1) 117.5(1) . 1_555 1_555 yes O(1) C(2) C(3) 122.1(1) . 1_555 1_555 yes C(1) C(2) C(3) 120.4(1) . 1_555 1_555 yes C(2) C(3) C(4) 119.7(1) . 1_555 1_555 yes C(2) C(3) C(7) 121.0(1) . 1_555 1_555 yes C(4) C(3) C(7) 119.2(1) . 1_555 1_555 yes C(3) C(4) C(5) 120.2(1) . 1_555 1_555 yes C(4) C(5) C(6) 119.1(1) . 1_555 1_555 yes C(1) C(6) C(5) 122.9(1) . 1_555 1_555 yes O(2) C(7) C(3) 124.3(1) . 1_555 1_555 yes C(1) C(8) C(9) 115.9(1) . 1_555 1_555 yes C(8) C(9) C(10) 124.4(1) . 1_555 1_555 yes C(8) C(9) C(11) 114.1(1) . 1_555 1_555 yes C(10) C(9) C(11) 121.4(1) . 1_555 1_555 yes C(9) C(11) C(12) 113.35(10) . 1_555 1_555 yes C(11) C(12) C(13) 121.6(1) . 1_555 1_555 yes C(11) C(12) C(17) 120.3(1) . 1_555 1_555 yes C(13) C(12) C(17) 118.0(1) . 1_555 1_555 yes C(12) C(13) C(14) 122.1(1) . 1_555 1_555 yes C(13) C(14) C(15) 119.3(1) . 1_555 1_555 yes C(14) C(15) C(16) 120.7(1) . 1_555 1_555 yes C(15) C(16) C(17) 119.3(1) . 1_555 1_555 yes C(15) C(16) C(18) 119.9(1) . 1_555 1_555 yes C(17) C(16) C(18) 120.8(1) . 1_555 1_555 yes O(3) C(17) C(12) 117.94(10) . 1_555 1_555 yes O(3) C(17) C(16) 121.6(1) . 1_555 1_555 yes C(12) C(17) C(16) 120.5(1) . 1_555 1_555 yes O(4) C(18) C(16) 124.9(1) . 1_555 1_555 yes #------------------------------------------------------------------------------ loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O(1) C(2) C(1) C(6) -179.6(1) 1_555 1_555 1_555 1_555 yes O(1) C(2) C(1) C(8) -0.2(2) 1_555 1_555 1_555 1_555 yes O(1) C(2) C(3) C(4) 179.5(1) 1_555 1_555 1_555 1_555 yes O(1) C(2) C(3) C(7) 0.1(2) 1_555 1_555 1_555 1_555 yes O(2) C(7) C(3) C(2) -0.2(2) 1_555 1_555 1_555 1_555 yes O(2) C(7) C(3) C(4) -179.6(1) 1_555 1_555 1_555 1_555 yes O(3) C(17) C(12) C(11) 1.1(2) 1_555 1_555 1_555 1_555 yes O(3) C(17) C(12) C(13) 178.8(1) 1_555 1_555 1_555 1_555 yes O(3) C(17) C(16) C(15) -178.8(1) 1_555 1_555 1_555 1_555 yes O(3) C(17) C(16) C(18) 1.9(2) 1_555 1_555 1_555 1_555 yes O(4) C(18) C(16) C(15) -179.6(1) 1_555 1_555 1_555 1_555 yes O(4) C(18) C(16) C(17) -0.3(2) 1_555 1_555 1_555 1_555 yes C(1) C(2) C(3) C(4) -0.1(2) 1_555 1_555 1_555 1_555 yes C(1) C(2) C(3) C(7) -179.5(1) 1_555 1_555 1_555 1_555 yes C(1) C(6) C(5) C(4) 0.4(2) 1_555 1_555 1_555 1_555 yes C(1) C(8) C(9) C(10) 8.5(2) 1_555 1_555 1_555 1_555 yes C(1) C(8) C(9) C(11) -171.9(1) 1_555 1_555 1_555 1_555 yes C(2) C(1) C(6) C(5) -0.2(2) 1_555 1_555 1_555 1_555 yes C(2) C(1) C(8) C(9) 86.4(1) 1_555 1_555 1_555 1_555 yes C(2) C(3) C(4) C(5) 0.3(2) 1_555 1_555 1_555 1_555 yes C(3) C(2) C(1) C(6) 0.0(2) 1_555 1_555 1_555 1_555 yes C(3) C(2) C(1) C(8) 179.4(1) 1_555 1_555 1_555 1_555 yes C(3) C(4) C(5) C(6) -0.5(2) 1_555 1_555 1_555 1_555 yes C(5) C(4) C(3) C(7) 179.8(1) 1_555 1_555 1_555 1_555 yes C(5) C(6) C(1) C(8) -179.6(1) 1_555 1_555 1_555 1_555 yes C(6) C(1) C(8) C(9) -94.3(1) 1_555 1_555 1_555 1_555 yes C(8) C(9) C(11) C(12) 77.5(1) 1_555 1_555 1_555 1_555 yes C(9) C(11) C(12) C(13) 36.1(2) 1_555 1_555 1_555 1_555 yes C(9) C(11) C(12) C(17) -146.3(1) 1_555 1_555 1_555 1_555 yes C(10) C(9) C(11) C(12) -102.9(1) 1_555 1_555 1_555 1_555 yes C(11) C(12) C(13) C(14) 178.3(1) 1_555 1_555 1_555 1_555 yes C(11) C(12) C(17) C(16) -179.2(1) 1_555 1_555 1_555 1_555 yes C(12) C(13) C(14) C(15) 0.3(2) 1_555 1_555 1_555 1_555 yes C(12) C(17) C(16) C(15) 1.4(2) 1_555 1_555 1_555 1_555 yes C(12) C(17) C(16) C(18) -177.9(1) 1_555 1_555 1_555 1_555 yes C(13) C(12) C(17) C(16) -1.5(2) 1_555 1_555 1_555 1_555 yes C(13) C(14) C(15) C(16) -0.3(2) 1_555 1_555 1_555 1_555 yes C(14) C(13) C(12) C(17) 0.6(2) 1_555 1_555 1_555 1_555 yes C(14) C(15) C(16) C(17) -0.6(2) 1_555 1_555 1_555 1_555 yes C(14) C(15) C(16) C(18) 178.8(1) 1_555 1_555 1_555 1_555 yes #------------------------------------------------------------------------------ loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 _geom_contact_publ_flag O(1) O(4) 2.945(1) . 4_555 ? O(1) O(3) 3.125(1) . 4_555 ? O(1) C(14) 3.546(2) . 3_766 ? O(2) C(10) 3.401(2) . 1_655 ? O(2) C(15) 3.475(2) . 2_756 ? O(2) C(15) 3.569(2) . 3_766 ? O(3) C(5) 3.504(2) . 2_645 ? O(3) C(13) 3.583(2) . 4_455 ? O(4) C(18) 3.334(2) . 3_756 ? O(4) C(13) 3.456(2) . 2_646 ? O(4) C(14) 3.472(2) . 2_646 ? O(4) O(4) 3.482(2) . 3_756 ? C(12) C(18) 3.518(2) . 4_455 ? C(12) C(16) 3.518(2) . 4_455 ? C(13) C(18) 3.553(2) . 4_455 ? C(15) C(17) 3.475(2) . 4_555 ? C(15) C(16) 3.590(2) . 4_555 ? C(16) C(17) 3.576(2) . 4_555 ? #------------------------------------------------------------------------------ #------------------------------------------------------------------------------ data_al #------------------------------------------------------------------------------ # CHEMICAL DATA _chemical_formula_sum 'C18 H16 O4 ' _chemical_formula_moiety 'C18 H16 O4 ' _chemical_formula_weight 296.32 _chemical_melting_point ? #------------------------------------------------------------------------------ # CRYSTAL DATA _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/n 1' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_as_xyz x,y,z 1/2-x,1/2+y,1/2-z -x,-y,-z 1/2+x,1/2-y,1/2+z _cell_length_a 7.7370(3) _cell_length_b 13.7793(6) _cell_length_c 14.5413(4) _cell_angle_alpha 90 _cell_angle_beta 101.431(1) _cell_angle_gamma 90 _cell_volume 1519.50(10) _cell_formula_units_Z 4 _cell_measurement_reflns_used 9531 _cell_measurement_theta_min 2.8 _cell_measurement_theta_max 27.5 _cell_measurement_temperature 193.2 #------------------------------------------------------------------------------ _exptl_crystal_description 'prism' _exptl_crystal_colour 'colorless' _exptl_crystal_size_max 0.600 _exptl_crystal_size_mid 0.400 _exptl_crystal_size_min 0.300 _exptl_crystal_size_rad ? _exptl_crystal_density_diffrn 1.295 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_absorpt_coefficient_mu 0.091 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(Higashi, 1995)' _exptl_absorpt_correction_T_min 0.857 _exptl_absorpt_correction_T_max 0.973 #------------------------------------------------------------------------------ # EXPERIMENTAL DATA _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.7107 _diffrn_measurement_device_type 'Rigaku RAXIS-RAPID Imaging Plate' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 3572 _diffrn_reflns_av_R_equivalents 0.023 _diffrn_reflns_theta_max 27.48 _diffrn_measured_fraction_theta_max 0.9856 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.9856 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 #------------------------------------------------------------------------------ # REFINEMENT DATA _refine_special_details ; Refinement using reflections with F^2^ > 1.5 sigma(F^2^). The weighted R-factor (wR) and goodness of fit (S) are based on F^2^. R-factor (gt) are based on F. The threshold expression of F^2^ > 2.0 sigma(F^2^) is used only for calculating R-factor (gt). ; _reflns_number_total 3427 _reflns_number_gt 2463 _reflns_threshold_expression F^2^>2.0\s(F^2^) _refine_ls_structure_factor_coef Fsqd _refine_ls_R_factor_gt 0.0436 _refine_ls_wR_factor_ref 0.0734 _refine_ls_hydrogen_treatment refxyz _refine_ls_number_reflns 2595 _refine_ls_number_parameters 247 _refine_ls_goodness_of_fit_ref 2.607 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^) + (0.01000(Max(Fo^2^,0) + 2Fc^2^)/3)^2^]' _refine_ls_shift/su_max 0.0003 _refine_diff_density_max 0.19 _refine_diff_density_min -0.29 _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details ? _refine_ls_abs_structure_Flack ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.003 0.002 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; 'H' 'H' 0.000 0.000 ;International Tables for Crystallography (1992, Vol. C, Table 6.1.1.2) ; 'O' 'O' 0.011 0.006 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; #------------------------------------------------------------------------------ # ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O(1) O 0.6282(1) 0.32091(8) 0.60583(6) 0.0409(3) Uani 1.00 d . . . O(2) O 0.8019(2) 0.3365(1) 0.87993(8) 0.0884(5) Uani 1.00 d . . . O(3) O 0.5757(1) 0.34911(6) 0.31088(6) 0.0361(3) Uani 1.00 d . . . O(4) O 0.6885(2) 0.12047(10) 0.16940(10) 0.0790(5) Uani 1.00 d . . . C(1) C 0.5787(2) 0.2444(1) 0.65431(9) 0.0387(4) Uani 1.00 d . . . C(2) C 0.6385(2) 0.2475(1) 0.75210(10) 0.0449(5) Uani 1.00 d . . . C(3) C 0.5893(2) 0.1723(2) 0.8065(1) 0.0585(6) Uani 1.00 d . . . C(4) C 0.4887(2) 0.0964(2) 0.7664(1) 0.0641(6) Uani 1.00 d . . . C(5) C 0.4335(2) 0.0939(1) 0.6705(1) 0.0570(6) Uani 1.00 d . . . C(6) C 0.4765(2) 0.1674(1) 0.6138(1) 0.0458(5) Uani 1.00 d . . . C(7) C 0.7514(3) 0.3265(1) 0.7959(1) 0.0581(6) Uani 1.00 d . . . C(8) C 0.5605(2) 0.3248(1) 0.50708(9) 0.0364(4) Uani 1.00 d . . . C(9) C 0.6392(2) 0.4096(1) 0.46640(9) 0.0324(4) Uani 1.00 d . . . C(10) C 0.7725(2) 0.4615(1) 0.5116(1) 0.0419(5) Uani 1.00 d . . . C(11) C 0.5541(2) 0.4331(1) 0.36704(10) 0.0332(4) Uani 1.00 d . . . C(12) C 0.5205(2) 0.3561(1) 0.21624(9) 0.0325(4) Uani 1.00 d . . . C(13) C 0.5580(2) 0.2761(1) 0.16394(10) 0.0378(4) Uani 1.00 d . . . C(14) C 0.5042(2) 0.2790(1) 0.0663(1) 0.0526(5) Uani 1.00 d . . . C(15) C 0.4175(3) 0.3577(2) 0.0224(1) 0.0608(6) Uani 1.00 d . . . C(16) C 0.3815(2) 0.4352(1) 0.0745(1) 0.0540(6) Uani 1.00 d . . . C(17) C 0.4321(2) 0.4360(1) 0.1712(1) 0.0404(4) Uani 1.00 d . . . C(18) C 0.6565(2) 0.1933(1) 0.2097(1) 0.0518(5) Uani 1.00 d . . . H(1) H 0.630(2) 0.178(1) 0.872(1) 0.0623 Uiso 1.00 calc . . . H(2) H 0.456(2) 0.0456(10) 0.8037(10) 0.0380 Uiso 1.00 calc . . . H(3) H 0.365(2) 0.039(1) 0.6408(9) 0.0380 Uiso 1.00 calc . . . H(4) H 0.432(2) 0.164(1) 0.547(1) 0.0623 Uiso 1.00 calc . . . H(5) H 0.790(2) 0.376(1) 0.7532(10) 0.0380 Uiso 1.00 calc . . . H(6) H 0.589(2) 0.265(1) 0.4778(9) 0.0380 Uiso 1.00 calc . . . H(7) H 0.427(2) 0.330(1) 0.496(1) 0.0623 Uiso 1.00 calc . . . H(8) H 0.826(2) 0.446(1) 0.576(1) 0.0623 Uiso 1.00 calc . . . H(9) H 0.819(2) 0.514(1) 0.483(1) 0.0623 Uiso 1.00 calc . . . H(10) H 0.424(2) 0.4455(10) 0.3617(9) 0.0380 Uiso 1.00 calc . . . H(11) H 0.611(2) 0.493(1) 0.345(1) 0.0623 Uiso 1.00 calc . . . H(12) H 0.532(2) 0.223(1) 0.0354(9) 0.0380 Uiso 1.00 calc . . . H(13) H 0.383(2) 0.357(1) -0.047(1) 0.0623 Uiso 1.00 calc . . . H(14) H 0.319(2) 0.493(1) 0.0466(9) 0.0380 Uiso 1.00 calc . . . H(15) H 0.409(2) 0.492(1) 0.206(1) 0.0623 Uiso 1.00 calc . . . H(16) H 0.704(2) 0.197(1) 0.279(1) 0.0623 Uiso 1.00 calc . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 O(1) 0.0477(6) 0.0491(7) 0.0244(5) -0.0014(5) 0.0031(4) 0.0027(5) O(2) 0.140(1) 0.081(1) 0.0327(7) 0.0409(10) -0.0121(7) -0.0103(6) O(3) 0.0514(6) 0.0308(6) 0.0266(5) 0.0054(5) 0.0088(4) -0.0017(4) O(4) 0.0876(10) 0.0528(8) 0.099(1) 0.0100(7) 0.0253(8) -0.0338(8) C(1) 0.0334(8) 0.052(1) 0.0319(8) 0.0137(8) 0.0098(6) 0.0100(7) C(2) 0.0425(9) 0.061(1) 0.0325(8) 0.0257(9) 0.0097(7) 0.0065(8) C(3) 0.053(1) 0.090(2) 0.0348(9) 0.035(1) 0.0155(8) 0.023(1) C(4) 0.046(1) 0.085(2) 0.065(1) 0.016(1) 0.0214(10) 0.045(1) C(5) 0.0392(10) 0.066(1) 0.065(1) 0.0009(9) 0.0078(9) 0.0255(10) C(6) 0.0376(9) 0.058(1) 0.0414(9) 0.0018(8) 0.0063(7) 0.0137(8) C(7) 0.076(1) 0.062(1) 0.0327(9) 0.034(1) 0.0028(8) -0.0010(8) C(8) 0.0406(8) 0.0426(9) 0.0240(7) -0.0016(8) 0.0017(6) 0.0016(7) C(9) 0.0362(8) 0.0314(8) 0.0307(7) 0.0031(7) 0.0093(6) -0.0041(6) C(10) 0.0423(9) 0.0436(10) 0.0387(9) -0.0036(8) 0.0057(7) -0.0045(8) C(11) 0.0416(9) 0.0287(8) 0.0299(7) 0.0012(7) 0.0086(6) -0.0034(6) C(12) 0.0344(8) 0.0374(9) 0.0278(7) -0.0083(7) 0.0114(6) -0.0015(6) C(13) 0.0385(8) 0.0405(9) 0.0379(8) -0.0113(7) 0.0160(7) -0.0094(7) C(14) 0.062(1) 0.058(1) 0.0434(10) -0.0226(10) 0.0247(9) -0.0213(9) C(15) 0.074(1) 0.078(1) 0.0302(8) -0.025(1) 0.0074(9) 0.0002(10) C(16) 0.062(1) 0.059(1) 0.0380(9) -0.0089(10) 0.0033(8) 0.0130(9) C(17) 0.0483(9) 0.0397(9) 0.0337(8) -0.0027(8) 0.0094(7) 0.0038(7) C(18) 0.052(1) 0.043(1) 0.063(1) -0.0013(9) 0.0188(9) -0.0163(9) #------------------------------------------------------------------------------ _computing_data_collection 'PROCESS-AUTO' _computing_cell_refinement 'PROCESS-AUTO' _computing_data_reduction 'teXsan Ver. 1.10' _computing_structure_solution SIR92 _computing_structure_refinement 'teXsan Ver. 1.10' _computing_publication_material 'teXsan Ver. 1.10' _computing_molecular_graphics ? #------------------------------------------------------------------------------ _geom_special_details ; ? ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag O(1) C(1) 1.364(2) . . yes O(1) C(8) 1.429(2) . . yes O(2) C(7) 1.215(2) . . yes O(3) C(11) 1.446(2) . . yes O(3) C(12) 1.361(2) . . yes O(4) C(18) 1.213(2) . . yes C(1) C(2) 1.406(2) . . yes C(1) C(6) 1.384(2) . . yes C(2) C(3) 1.401(2) . . yes C(2) C(7) 1.461(2) . . yes C(3) C(4) 1.363(3) . . yes C(4) C(5) 1.376(3) . . yes C(5) C(6) 1.387(2) . . yes C(8) C(9) 1.494(2) . . yes C(9) C(10) 1.318(2) . . yes C(9) C(11) 1.500(2) . . yes C(12) C(13) 1.402(2) . . yes C(12) C(17) 1.390(2) . . yes C(13) C(14) 1.398(2) . . yes C(13) C(18) 1.457(2) . . yes C(14) C(15) 1.367(3) . . yes C(15) C(16) 1.369(3) . . yes C(16) C(17) 1.383(2) . . yes #------------------------------------------------------------------------------ loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C(1) O(1) C(8) 117.6(1) . 1_555 1_555 yes C(11) O(3) C(12) 117.8(1) . 1_555 1_555 yes O(1) C(1) C(2) 115.4(1) . 1_555 1_555 yes O(1) C(1) C(6) 124.6(1) . 1_555 1_555 yes C(2) C(1) C(6) 120.0(1) . 1_555 1_555 yes C(1) C(2) C(3) 118.5(2) . 1_555 1_555 yes C(1) C(2) C(7) 120.8(1) . 1_555 1_555 yes C(3) C(2) C(7) 120.7(2) . 1_555 1_555 yes C(2) C(3) C(4) 121.4(2) . 1_555 1_555 yes C(3) C(4) C(5) 119.3(2) . 1_555 1_555 yes C(4) C(5) C(6) 121.4(2) . 1_555 1_555 yes C(1) C(6) C(5) 119.4(2) . 1_555 1_555 yes O(2) C(7) C(2) 124.6(2) . 1_555 1_555 yes O(1) C(8) C(9) 109.3(1) . 1_555 1_555 yes C(8) C(9) C(10) 124.6(1) . 1_555 1_555 yes C(8) C(9) C(11) 114.5(1) . 1_555 1_555 yes C(10) C(9) C(11) 120.9(1) . 1_555 1_555 yes O(3) C(11) C(9) 107.0(1) . 1_555 1_555 yes O(3) C(12) C(13) 115.8(1) . 1_555 1_555 yes O(3) C(12) C(17) 124.0(1) . 1_555 1_555 yes C(13) C(12) C(17) 120.2(1) . 1_555 1_555 yes C(12) C(13) C(14) 118.5(2) . 1_555 1_555 yes C(12) C(13) C(18) 120.9(1) . 1_555 1_555 yes C(14) C(13) C(18) 120.6(2) . 1_555 1_555 yes C(13) C(14) C(15) 121.1(2) . 1_555 1_555 yes C(14) C(15) C(16) 119.7(2) . 1_555 1_555 yes C(15) C(16) C(17) 121.5(2) . 1_555 1_555 yes C(12) C(17) C(16) 119.1(2) . 1_555 1_555 yes O(4) C(18) C(13) 124.4(2) . 1_555 1_555 yes #------------------------------------------------------------------------------ loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O(1) C(1) C(2) C(3) 178.6(1) 1_555 1_555 1_555 1_555 yes O(1) C(1) C(2) C(7) -2.3(2) 1_555 1_555 1_555 1_555 yes O(1) C(1) C(6) C(5) -179.5(1) 1_555 1_555 1_555 1_555 yes O(1) C(8) C(9) C(10) 11.0(2) 1_555 1_555 1_555 1_555 yes O(1) C(8) C(9) C(11) -169.0(1) 1_555 1_555 1_555 1_555 yes O(2) C(7) C(2) C(1) 176.6(2) 1_555 1_555 1_555 1_555 yes O(2) C(7) C(2) C(3) -4.3(3) 1_555 1_555 1_555 1_555 yes O(3) C(11) C(9) C(8) -60.9(2) 1_555 1_555 1_555 1_555 yes O(3) C(11) C(9) C(10) 119.1(1) 1_555 1_555 1_555 1_555 yes O(3) C(12) C(13) C(14) 179.8(1) 1_555 1_555 1_555 1_555 yes O(3) C(12) C(13) C(18) -2.4(2) 1_555 1_555 1_555 1_555 yes O(3) C(12) C(17) C(16) -179.8(1) 1_555 1_555 1_555 1_555 yes O(4) C(18) C(13) C(12) 177.5(2) 1_555 1_555 1_555 1_555 yes O(4) C(18) C(13) C(14) -4.8(3) 1_555 1_555 1_555 1_555 yes C(1) O(1) C(8) C(9) -176.2(1) 1_555 1_555 1_555 1_555 yes C(1) C(2) C(3) C(4) 1.3(2) 1_555 1_555 1_555 1_555 yes C(1) C(6) C(5) C(4) 0.7(3) 1_555 1_555 1_555 1_555 yes C(2) C(1) O(1) C(8) -175.6(1) 1_555 1_555 1_555 1_555 yes C(2) C(1) C(6) C(5) 0.2(2) 1_555 1_555 1_555 1_555 yes C(2) C(3) C(4) C(5) -0.3(3) 1_555 1_555 1_555 1_555 yes C(3) C(2) C(1) C(6) -1.2(2) 1_555 1_555 1_555 1_555 yes C(3) C(4) C(5) C(6) -0.7(3) 1_555 1_555 1_555 1_555 yes C(4) C(3) C(2) C(7) -177.9(2) 1_555 1_555 1_555 1_555 yes C(6) C(1) O(1) C(8) 4.2(2) 1_555 1_555 1_555 1_555 yes C(6) C(1) C(2) C(7) 177.9(1) 1_555 1_555 1_555 1_555 yes C(9) C(11) O(3) C(12) -175.0(1) 1_555 1_555 1_555 1_555 yes C(11) O(3) C(12) C(13) 174.6(1) 1_555 1_555 1_555 1_555 yes C(11) O(3) C(12) C(17) -5.5(2) 1_555 1_555 1_555 1_555 yes C(12) C(13) C(14) C(15) 0.2(2) 1_555 1_555 1_555 1_555 yes C(12) C(17) C(16) C(15) -0.3(2) 1_555 1_555 1_555 1_555 yes C(13) C(12) C(17) C(16) 0.1(2) 1_555 1_555 1_555 1_555 yes C(13) C(14) C(15) C(16) -0.3(3) 1_555 1_555 1_555 1_555 yes C(14) C(13) C(12) C(17) -0.1(2) 1_555 1_555 1_555 1_555 yes C(14) C(15) C(16) C(17) 0.4(3) 1_555 1_555 1_555 1_555 yes C(15) C(14) C(13) C(18) -177.6(2) 1_555 1_555 1_555 1_555 yes C(17) C(12) C(13) C(18) 177.7(1) 1_555 1_555 1_555 1_555 yes #------------------------------------------------------------------------------ loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 _geom_contact_publ_flag O(1) C(14) 3.369(2) . 4_555 ? O(1) C(13) 3.528(2) . 4_555 ? O(2) C(8) 3.301(2) . 4_555 ? O(2) C(6) 3.401(2) . 4_555 ? O(2) C(16) 3.567(3) . 3_666 ? O(2) O(3) 3.589(2) . 4_555 ? O(3) C(7) 3.462(2) . 4_454 ? O(3) C(4) 3.466(2) . 4_554 ? O(3) C(2) 3.578(2) . 4_454 ? O(4) C(11) 3.366(2) . 2_645 ? O(4) C(10) 3.483(2) . 2_645 ? O(4) C(4) 3.491(3) . 3_656 ? O(4) C(1) 3.591(2) . 4_554 ? C(2) C(12) 3.414(2) . 4_555 ? C(5) C(13) 3.398(2) . 4_455 ? C(5) C(12) 3.460(2) . 4_455 ? C(6) C(13) 3.544(2) . 4_455 ? C(6) C(16) 3.585(2) . 4_555 ? C(9) C(9) 3.554(3) . 3_666 ? C(16) C(16) 3.581(3) . 3_665 ? #------------------------------------------------------------------------------