data_General _audit_creation_date '2007-05-07' _audit_creation_method 'by CrystalStructure 3.8' _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 'Masahiko Shibahara' _publ_contact_author_email 'mshiba@cc.oita-u.ac.jp' _publ_contact_author_fax '+81 97 554 7553' _publ_contact_author_phone '+81 97 554 7553' _publ_contact_letter ; ENTER TEXT OF LETTER ; _publ_requested_journal 'The Journal of Organic Chemistry' _publ_requested_category 'FO' _publ_requested_coeditor_name ? #============================================================================== # TITLE AND AUTHOR LIST _publ_section_title ; ENTER SECTION TITLE ; _publ_section_title_footnote ; ENTER FOOTNOTE TO TITLE OF PAPER ; loop_ _publ_author_name _publ_author_footnote _publ_author_address ' FIRST AUTHORS NAME ' ; FIRST AUTHORS FOOTNOTES ; ; FIRST AUTHORS ADDRESS ; _publ_section_synopsis ; ENTER SYNOPSIS ; #============================================================================== # TEXT _publ_section_abstract ; ENTER ABSTRACT ; _publ_section_comment ; ENTER TEXT ; _publ_section_references ; ENTER OTHER REFERENCES Rigaku/MSC and Rigaku Corporation. (2006). CrystalStructure (Version 3.8). Single Crystal Structure Analysis Software. Rigaku/MSC, 9009 TX, USA 77381-5209. Rigaku, Tokyo 196-8666, Japan. Sheldrick, G.M. (1997). SHELXL97. University of Gottingen, Germany. ; _publ_section_figure_captions ; ENTER FIGURE CAPTIONS ; _publ_section_exptl_prep ; ENTER COMPOUND PREPARATION DETAILS ; _publ_section_exptl_refinement ; ENTER SPECIAL DETAILS OF THE REFINEMENT ; #============================================================================== data__sh0705b #============================================================================== # CHEMICAL DATA _chemical_formula_sum 'C18 H16 O2 ' _chemical_formula_moiety 'C18 H16 O2 ' _chemical_formula_weight 264.32 _chemical_melting_point ? #============================================================================== # CRYSTAL DATA _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/c 1' _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 '+X,+Y,+Z' 2 '-X,1/2+Y,1/2-Z' 3 '-X,-Y,-Z' 4 '+X,1/2-Y,1/2+Z' #------------------------------------------------------------------------------ _cell_length_a 6.1422(10) _cell_length_b 12.7937(19) _cell_length_c 8.6322(14) _cell_angle_alpha 90.0000 _cell_angle_beta 105.270(11) _cell_angle_gamma 90.0000 _cell_volume 654.38(18) _cell_formula_units_Z 2 _cell_measurement_reflns_used 8118 _cell_measurement_theta_min 3.5 _cell_measurement_theta_max 68.2 _cell_measurement_temperature 123.1 #------------------------------------------------------------------------------ _exptl_crystal_description 'prism' _exptl_crystal_colour 'colorless' _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.10 _exptl_crystal_density_diffrn 1.341 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 280.00 _exptl_absorpt_coefficient_mu 0.685 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; Higashi, T. (1995). Program for Absorption Correction. Rigaku Corporation, Tokyo, Japan. ; _exptl_absorpt_correction_T_min 0.706 _exptl_absorpt_correction_T_max 0.934 #============================================================================== # EXPERIMENTAL DATA _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54187 _diffrn_measurement_device_type 'Rigaku RAXIS-RAPID' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 5.00 _diffrn_reflns_number 8224 _diffrn_reflns_av_R_equivalents 0.027 _diffrn_reflns_theta_max 68.24 _diffrn_measured_fraction_theta_max 0.984 _diffrn_reflns_theta_full 68.24 _diffrn_measured_fraction_theta_full 0.984 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 #============================================================================== # REFINEMENT DATA _refine_special_details ; Refinement was performed using all reflections. 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 1177 _reflns_number_gt 1128 _reflns_threshold_expression F^2^>2.0\s(F^2^) _refine_ls_structure_factor_coef Fsqd _refine_ls_R_factor_gt 0.0367 _refine_ls_wR_factor_ref 0.0957 _refine_ls_hydrogen_treatment refall _refine_ls_number_reflns 1177 _refine_ls_number_parameters 93 _refine_ls_goodness_of_fit_ref 1.075 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.0457P)^2^+0.2724P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_shift/su_max 0.0010 _refine_diff_density_max 0.21 _refine_diff_density_min -0.16 _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0083(15) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.018 0.009 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; 'H' 'H' 0.000 0.000 ; International Tables for Crystallography (1992, Vol. C, Table 6.1.1.4) ; 'O' 'O' 0.049 0.032 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; #============================================================================== # ATOMIC COORDINATES AND THERMAL 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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O(1) O -0.00778(16) 0.86291(8) 0.64107(12) 0.0319(3) Uani 1.00 1 d . . . C(1) C 0.3030(2) 0.78773(10) 0.83435(14) 0.0246(3) Uani 1.00 1 d . . . C(2) C 0.1956(2) 0.86122(9) 0.69563(14) 0.0206(3) Uani 1.00 1 d . . . C(3) C 0.3443(2) 0.93383(10) 0.62701(15) 0.0237(3) Uani 1.00 1 d . . . C(4) C 0.4420(2) 1.02094(9) 0.74474(14) 0.0190(3) Uani 1.00 1 d . . . C(5) C 0.3005(2) 1.09289(10) 0.79164(15) 0.0217(3) Uani 1.00 1 d . . . C(6) C 0.3836(2) 1.15840(9) 0.92244(15) 0.0211(3) Uani 1.00 1 d . . . C(7) C 0.6104(2) 1.15485(9) 1.00731(14) 0.0196(3) Uani 1.00 1 d . . . C(8) C 0.7555(2) 1.09196(9) 0.94800(14) 0.0203(3) Uani 1.00 1 d . . . C(9) C 0.6719(2) 1.02532(9) 0.81904(14) 0.0193(3) Uani 1.00 1 d . . . H(1) H 0.1900 0.7352 0.8458 0.030 Uiso 1.00 1 c R . . H(2) H 0.4299 0.7501 0.8087 0.030 Uiso 1.00 1 c R . . H(3) H 0.4689 0.8931 0.6034 0.028 Uiso 1.00 1 c R . . H(4) H 0.2539 0.9646 0.5251 0.028 Uiso 1.00 1 c R . . H(5) H 0.1461 1.0971 0.7337 0.026 Uiso 1.00 1 c R . . H(6) H 0.2848 1.2060 0.9542 0.025 Uiso 1.00 1 c R . . H(7) H 0.9134 1.0947 0.9964 0.024 Uiso 1.00 1 c R . . H(8) H 0.7730 0.9823 0.7812 0.023 Uiso 1.00 1 c 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_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 O(1) 0.0248(5) 0.0329(5) 0.0346(5) -0.0033(4) 0.0019(4) -0.0039(4) C(1) 0.0348(7) 0.0184(6) 0.0207(6) -0.0005(5) 0.0074(5) -0.0016(4) C(2) 0.0253(6) 0.0188(6) 0.0165(6) -0.0013(4) 0.0036(5) -0.0074(4) C(3) 0.0300(7) 0.0244(6) 0.0163(6) -0.0028(5) 0.0054(5) -0.0014(5) C(4) 0.0250(6) 0.0183(6) 0.0141(5) -0.0019(4) 0.0061(4) 0.0032(4) C(5) 0.0185(6) 0.0231(6) 0.0230(6) -0.0001(4) 0.0044(5) 0.0030(4) C(6) 0.0241(6) 0.0177(5) 0.0242(6) 0.0023(4) 0.0112(5) 0.0022(4) C(7) 0.0275(6) 0.0149(5) 0.0168(6) -0.0002(4) 0.0066(5) 0.0028(4) C(8) 0.0195(6) 0.0216(6) 0.0184(6) 0.0017(4) 0.0023(4) 0.0029(4) C(9) 0.0238(6) 0.0188(6) 0.0166(6) 0.0039(4) 0.0075(5) 0.0025(4) #============================================================================== _computing_data_collection 'PROCESS-AUTO' _computing_cell_refinement 'PROCESS-AUTO' _computing_data_reduction 'CrystalStructure' _computing_structure_solution 'SIR97' _computing_structure_refinement 'SHELXL' _computing_publication_material 'CrystalStructure 3.8' _computing_molecular_graphics ? #============================================================================== # MOLECULAR GEOMETRY _geom_special_details ; ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 O(1) C(2) 1.2134(15) yes . . C(1) C(2) 1.5288(16) yes . . C(1) C(7) 1.5192(16) yes . 3_677 C(2) C(3) 1.5278(19) yes . . C(3) C(4) 1.5210(16) yes . . C(4) C(5) 1.3971(18) yes . . C(4) C(9) 1.3899(16) yes . . C(5) C(6) 1.3908(16) yes . . C(6) C(7) 1.3934(17) yes . . C(7) C(8) 1.3944(19) yes . . C(8) C(9) 1.3888(15) yes . . C(1) H(1) 0.990 no . . C(1) H(2) 0.990 no . . C(3) H(3) 0.990 no . . C(3) H(4) 0.990 no . . C(5) H(5) 0.950 no . . C(6) H(6) 0.950 no . . C(8) H(7) 0.950 no . . C(9) H(8) 0.950 no . . loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_publ_flag _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 C(2) C(1) C(7) 112.58(10) yes . . 3_677 O(1) C(2) C(1) 120.19(12) yes . . . O(1) C(2) C(3) 119.89(10) yes . . . C(1) C(2) C(3) 119.92(10) yes . . . C(2) C(3) C(4) 110.94(11) yes . . . C(3) C(4) C(5) 120.70(10) yes . . . C(3) C(4) C(9) 120.78(11) yes . . . C(5) C(4) C(9) 118.28(10) yes . . . C(4) C(5) C(6) 120.60(10) yes . . . C(5) C(6) C(7) 120.63(12) yes . . . C(1) C(7) C(6) 121.46(12) yes 3_677 . . C(1) C(7) C(8) 120.21(10) yes 3_677 . . C(6) C(7) C(8) 118.22(10) yes . . . C(7) C(8) C(9) 120.76(11) yes . . . C(4) C(9) C(8) 120.72(12) yes . . . C(2) C(1) H(1) 109.1 no . . . C(2) C(1) H(2) 109.1 no . . . C(7) C(1) H(1) 109.1 no 3_677 . . C(7) C(1) H(2) 109.1 no 3_677 . . H(1) C(1) H(2) 107.8 no . . . C(2) C(3) H(3) 109.5 no . . . C(2) C(3) H(4) 109.5 no . . . C(4) C(3) H(3) 109.5 no . . . C(4) C(3) H(4) 109.5 no . . . H(3) C(3) H(4) 108.0 no . . . C(4) C(5) H(5) 119.7 no . . . C(6) C(5) H(5) 119.7 no . . . C(5) C(6) H(6) 119.7 no . . . C(7) C(6) H(6) 119.7 no . . . C(7) C(8) H(7) 119.6 no . . . C(9) C(8) H(7) 119.6 no . . . C(4) C(9) H(8) 119.6 no . . . C(8) C(9) H(8) 119.6 no . . . 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_publ_flag _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 C(2) C(1) C(7) C(6) -120.27(13) ? . . 3_677 3_677 C(2) C(1) C(7) C(8) 55.99(16) ? . . 3_677 3_677 C(7) C(1) C(2) O(1) -106.62(14) ? 3_677 . . . C(7) C(1) C(2) C(3) 72.54(15) ? 3_677 . . . O(1) C(2) C(3) C(4) 108.18(12) ? . . . . C(1) C(2) C(3) C(4) -70.98(14) ? . . . . C(2) C(3) C(4) C(5) -62.13(14) ? . . . . C(2) C(3) C(4) C(9) 112.08(13) ? . . . . C(3) C(4) C(5) C(6) 166.59(12) ? . . . . C(3) C(4) C(9) C(8) -167.64(11) ? . . . . C(5) C(4) C(9) C(8) 6.71(18) ? . . . . C(9) C(4) C(5) C(6) -7.76(19) ? . . . . C(4) C(5) C(6) C(7) 1.2(2) ? . . . . C(5) C(6) C(7) C(1) -169.90(12) ? . . . 3_677 C(5) C(6) C(7) C(8) 6.43(18) ? . . . . C(1) C(7) C(8) C(9) 168.87(11) ? 3_677 . . . C(6) C(7) C(8) C(9) -7.51(18) ? . . . . C(7) C(8) C(9) C(4) 0.93(18) ? . . . . loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_publ_flag _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 O(1) C(6) 3.4363(15) ? . 2_546 O(1) C(9) 3.4843(17) ? . 1_455 C(1) C(7) 3.5634(18) ? . 2_646 C(1) C(8) 3.4469(17) ? . 2_646 C(2) C(7) 3.5440(17) ? . 2_646 C(6) O(1) 3.4363(15) ? . 2_556 C(7) C(1) 3.5634(18) ? . 2_656 C(7) C(2) 3.5440(17) ? . 2_656 C(8) C(1) 3.4469(17) ? . 2_656 C(9) O(1) 3.4843(17) ? . 1_655 O(1) H(1) 3.343 ? . 4_564 O(1) H(3) 3.168 ? . 1_455 O(1) H(4) 2.841 ? . 3_576 O(1) H(5) 3.162 ? . 3_576 O(1) H(6) 2.620 ? . 2_546 O(1) H(8) 2.543 ? . 1_455 C(1) H(3) 3.246 ? . 4_565 C(2) H(1) 3.253 ? . 4_564 C(2) H(6) 3.509 ? . 2_546 C(2) H(8) 3.270 ? . 1_455 C(3) H(1) 3.202 ? . 4_564 C(3) H(3) 3.373 ? . 3_676 C(3) H(4) 3.348 ? . 3_676 C(3) H(8) 3.571 ? . 3_676 C(4) H(2) 3.101 ? . 2_656 C(4) H(3) 3.378 ? . 3_676 C(4) H(4) 3.353 ? . 3_676 C(5) H(1) 3.452 ? . 2_556 C(5) H(2) 2.879 ? . 2_656 C(5) H(7) 3.315 ? . 1_455 C(5) H(8) 3.515 ? . 1_455 C(6) H(2) 2.806 ? . 2_656 C(6) H(3) 3.161 ? . 2_656 C(6) H(7) 3.222 ? . 1_455 C(7) H(2) 2.938 ? . 2_656 C(7) H(3) 3.193 ? . 2_656 C(8) H(1) 3.217 ? . 2_656 C(8) H(2) 2.995 ? . 2_656 C(8) H(5) 3.394 ? . 1_655 C(8) H(6) 3.551 ? . 1_655 C(8) H(7) 3.091 ? . 3_777 C(8) H(8) 3.345 ? . 3_777 C(9) H(1) 3.254 ? . 2_656 C(9) H(2) 3.084 ? . 2_656 C(9) H(4) 3.124 ? . 3_676 C(9) H(5) 3.317 ? . 1_655 C(9) H(7) 3.041 ? . 3_777 H(1) O(1) 3.343 ? . 4_565 H(1) C(2) 3.253 ? . 4_565 H(1) C(3) 3.202 ? . 4_565 H(1) C(5) 3.452 ? . 2_546 H(1) C(8) 3.217 ? . 2_646 H(1) C(9) 3.254 ? . 2_646 H(1) H(3) 2.927 ? . 4_565 H(1) H(4) 2.959 ? . 4_565 H(1) H(5) 2.666 ? . 2_546 H(1) H(6) 3.373 ? . 2_546 H(1) H(7) 3.372 ? . 2_646 H(1) H(8) 3.443 ? . 2_646 H(2) C(4) 3.101 ? . 2_646 H(2) C(5) 2.879 ? . 2_646 H(2) C(6) 2.806 ? . 2_646 H(2) C(7) 2.938 ? . 2_646 H(2) C(8) 2.995 ? . 2_646 H(2) C(9) 3.084 ? . 2_646 H(2) H(3) 3.093 ? . 4_565 H(2) H(5) 3.353 ? . 2_646 H(2) H(6) 3.261 ? . 2_646 H(2) H(7) 3.522 ? . 2_646 H(3) O(1) 3.168 ? . 1_655 H(3) C(1) 3.246 ? . 4_564 H(3) C(3) 3.373 ? . 3_676 H(3) C(4) 3.378 ? . 3_676 H(3) C(6) 3.161 ? . 2_646 H(3) C(7) 3.193 ? . 2_646 H(3) H(1) 2.927 ? . 4_564 H(3) H(2) 3.093 ? . 4_564 H(3) H(3) 3.343 ? . 3_676 H(3) H(4) 2.906 ? . 3_676 H(3) H(6) 2.943 ? . 2_646 H(4) O(1) 2.841 ? . 3_576 H(4) C(3) 3.348 ? . 3_676 H(4) C(4) 3.353 ? . 3_676 H(4) C(9) 3.124 ? . 3_676 H(4) H(1) 2.959 ? . 4_564 H(4) H(3) 2.906 ? . 3_676 H(4) H(4) 3.166 ? . 3_576 H(4) H(4) 3.293 ? . 3_676 H(4) H(5) 2.959 ? . 3_576 H(4) H(8) 2.692 ? . 3_676 H(5) O(1) 3.162 ? . 3_576 H(5) C(8) 3.394 ? . 1_455 H(5) C(9) 3.317 ? . 1_455 H(5) H(1) 2.666 ? . 2_556 H(5) H(2) 3.353 ? . 2_656 H(5) H(4) 2.959 ? . 3_576 H(5) H(7) 2.982 ? . 1_455 H(5) H(8) 2.842 ? . 1_455 H(6) O(1) 2.620 ? . 2_556 H(6) C(2) 3.509 ? . 2_556 H(6) C(8) 3.551 ? . 1_455 H(6) H(1) 3.373 ? . 2_556 H(6) H(2) 3.261 ? . 2_656 H(6) H(3) 2.943 ? . 2_656 H(6) H(7) 2.793 ? . 1_455 H(7) C(5) 3.315 ? . 1_655 H(7) C(6) 3.222 ? . 1_655 H(7) C(8) 3.091 ? . 3_777 H(7) C(9) 3.041 ? . 3_777 H(7) H(1) 3.372 ? . 2_656 H(7) H(2) 3.522 ? . 2_656 H(7) H(5) 2.982 ? . 1_655 H(7) H(6) 2.793 ? . 1_655 H(7) H(7) 2.641 ? . 3_777 H(7) H(8) 2.534 ? . 3_777 H(8) O(1) 2.543 ? . 1_655 H(8) C(2) 3.270 ? . 1_655 H(8) C(3) 3.571 ? . 3_676 H(8) C(5) 3.515 ? . 1_655 H(8) C(8) 3.345 ? . 3_777 H(8) H(1) 3.443 ? . 2_656 H(8) H(4) 2.692 ? . 3_676 H(8) H(5) 2.842 ? . 1_655 H(8) H(7) 2.534 ? . 3_777 #============================================================================== # Additional structures and associated data_? identifiers # should be added at this point if there is more than one # structure analysis in the CIF. #============================================================================== # End of CIF #==============================================================================