# Electronic Supplementary Material (ESI) for Chemical Science # This journal is © The Royal Society of Chemistry 2011 data_global _journal_coden_Cambridge 1475 _journal_volume ? _journal_page_first ? _journal_year ? loop_ _publ_author_name 'Dermenci, Alpay' 'Selig, Philipp' 'Domaoal, Robert' 'Spasov, Krasimir' 'Anderson, Karen' 'Miller, Scott' _publ_contact_author_name 'Dr Scott Miller' _publ_contact_author_email scott.miller@yale.edu _publ_section_title ; Quasi-Biomimetic Ring Contraction Catalyzed by a Cysteine-Based Nucleophile: Total Synthesis of Sch-642305, Some Analogs and their Putative anti-HIV Activities ; # Attachment '- (e)-Compound 5.cif' data_shelxl _database_code_depnum_ccdc_archive 'CCDC 820817' #TrackingRef '- (e)-Compound 5.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C30 H38 O4 Si' _chemical_formula_weight 490.69 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Si Si 0.2541 0.3302 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting ? _symmetry_space_group_name_H-M ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 9.7467(2) _cell_length_b 14.1261(3) _cell_length_c 20.0486(4) _cell_angle_alpha 90.00 _cell_angle_beta 95.8450(10) _cell_angle_gamma 90.00 _cell_volume 2746.01(10) _cell_formula_units_Z 4 _cell_measurement_temperature 93(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.187 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1056 _exptl_absorpt_coefficient_mu 1.006 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.8241 _exptl_absorpt_correction_T_max 0.8241 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 93(2) _diffrn_radiation_wavelength 1.54187 _diffrn_radiation_type CuK\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 24947 _diffrn_reflns_av_R_equivalents 0.0325 _diffrn_reflns_av_sigmaI/netI 0.0465 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 6.65 _diffrn_reflns_theta_max 66.59 _reflns_number_total 8748 _reflns_number_gt 7734 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _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^)+(0.1250P)^2^+3.0032P] 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 0.01(4) _refine_ls_number_reflns 8748 _refine_ls_number_parameters 627 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0863 _refine_ls_R_factor_gt 0.0779 _refine_ls_wR_factor_ref 0.2246 _refine_ls_wR_factor_gt 0.2133 _refine_ls_goodness_of_fit_ref 1.112 _refine_ls_restrained_S_all 1.112 _refine_ls_shift/su_max 1.250 _refine_ls_shift/su_mean 0.048 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 Si1 Si 0.64356(16) 0.70830(9) 0.07076(6) 0.0323(3) Uani 1 1 d . . . Si2 Si 0.40455(16) 0.98135(9) 0.33784(6) 0.0339(3) Uani 1 1 d . . . O1 O 0.6145(4) 0.6572(3) 0.14113(17) 0.0424(9) Uani 1 1 d . . . O2 O 0.3104(4) 0.8897(2) 0.35493(18) 0.0393(9) Uani 1 1 d . . . O3 O 0.6077(6) 0.5679(4) 0.3540(2) 0.0678(14) Uani 1 1 d . . . O4 O 0.5961(5) 0.3289(3) 0.2328(3) 0.0696(15) Uani 1 1 d . . . O5 O 0.8184(5) 0.3148(3) 0.2734(2) 0.0475(10) Uani 1 1 d . . . O6 O 0.0888(6) 0.6389(4) 0.1978(3) 0.0814(19) Uani 1 1 d . . . O7 O 0.1181(6) 0.5994(4) 0.4069(2) 0.0664(14) Uani 1 1 d . . . O8 O 0.2723(5) 0.5427(3) 0.1949(2) 0.0513(11) Uani 1 1 d . . . C1 C 0.8930(7) 0.9897(4) 0.1097(3) 0.0496(15) Uani 1 1 d . . . H1 H 0.9440 1.0468 0.1162 0.060 Uiso 1 1 calc R . . C2 C 0.7566(7) 0.9918(4) 0.0864(3) 0.0526(16) Uani 1 1 d . . . H2 H 0.7117 1.0507 0.0768 0.063 Uiso 1 1 calc R . . C3 C 0.6832(6) 0.9077(4) 0.0765(3) 0.0430(13) Uani 1 1 d . . . H3 H 0.5875 0.9103 0.0617 0.052 Uiso 1 1 calc R . . C4 C 0.7454(6) 0.8204(4) 0.0875(2) 0.0323(11) Uani 1 1 d . . . C5 C 0.9557(7) 0.9034(5) 0.1239(4) 0.0532(16) Uani 1 1 d . . . H4 H 1.0499 0.9013 0.1416 0.064 Uiso 1 1 calc R . . C6 C 0.8833(7) 0.8203(4) 0.1126(3) 0.0511(16) Uani 1 1 d . . . H5 H 0.9287 0.7616 0.1222 0.061 Uiso 1 1 calc R . . C7 C 0.7807(7) 0.6765(4) -0.0456(3) 0.0442(14) Uani 1 1 d . . . H6 H 0.7069 0.6769 -0.0827 0.053 Uiso 1 1 calc R . . H7 H 0.8621 0.6447 -0.0600 0.053 Uiso 1 1 calc R . . H8 H 0.8045 0.7418 -0.0325 0.053 Uiso 1 1 calc R . . C8 C 0.7314(6) 0.6231(4) 0.0146(2) 0.0372(12) Uani 1 1 d . . . C9 C 0.8529(7) 0.5720(4) 0.0509(3) 0.0460(14) Uani 1 1 d . . . H9 H 0.9370 0.6090 0.0477 0.055 Uiso 1 1 calc R . . H10 H 0.8628 0.5097 0.0304 0.055 Uiso 1 1 calc R . . H11 H 0.8379 0.5640 0.0982 0.055 Uiso 1 1 calc R . . C10 C 0.6227(7) 0.5492(4) -0.0111(3) 0.0438(14) Uani 1 1 d . . . H12 H 0.6263 0.4955 0.0199 0.053 Uiso 1 1 calc R . . H13 H 0.6417 0.5271 -0.0556 0.053 Uiso 1 1 calc R . . H14 H 0.5307 0.5779 -0.0141 0.053 Uiso 1 1 calc R . . C11 C 0.2170(9) 0.7473(8) 0.0458(6) 0.103(4) Uani 1 1 d . . . H15 H 0.1430 0.7378 0.0725 0.124 Uiso 1 1 calc R . . C12 C 0.3536(9) 0.7253(6) 0.0712(4) 0.077(2) Uani 1 1 d . . . H16 H 0.3704 0.7002 0.1152 0.093 Uiso 1 1 calc R . . C13 C 0.1932(9) 0.7820(6) -0.0170(5) 0.081(3) Uani 1 1 d . . . H17 H 0.1011 0.7953 -0.0348 0.098 Uiso 1 1 calc R . . C14 C 0.4645(6) 0.7394(4) 0.0338(3) 0.0363(12) Uani 1 1 d . . . C15 C 0.4348(7) 0.7764(4) -0.0305(3) 0.0505(15) Uani 1 1 d . . . H18 H 0.5076 0.7870 -0.0578 0.061 Uiso 1 1 calc R . . C16 C 0.2978(8) 0.7985(5) -0.0557(4) 0.0629(19) Uani 1 1 d . . . H19 H 0.2788 0.8247 -0.0993 0.075 Uiso 1 1 calc R . . C17 C 0.7034(8) 0.6884(4) 0.2548(3) 0.0508(16) Uani 1 1 d . . . H20 H 0.7342 0.7526 0.2434 0.061 Uiso 1 1 calc R . . H21 H 0.6063 0.6930 0.2649 0.061 Uiso 1 1 calc R . . C18 C 0.7918(8) 0.6533(4) 0.3171(3) 0.0514(16) Uani 1 1 d . . . H63 H 0.8835 0.6351 0.3040 0.062 Uiso 1 1 calc R . . H64 H 0.8059 0.7064 0.3493 0.062 Uiso 1 1 calc R . . C19 C 0.7109(7) 0.6236(4) 0.1945(2) 0.0412(13) Uani 1 1 d . . . H22 H 0.8063 0.6244 0.1802 0.049 Uiso 1 1 calc R . . C20 C 0.6685(8) 0.5235(4) 0.2075(3) 0.0498(16) Uani 1 1 d . . . H65 H 0.5730 0.5086 0.2038 0.060 Uiso 1 1 calc R . . C21 C 0.7334(6) 0.5715(4) 0.3515(2) 0.0352(12) Uani 1 1 d . . . C22 C 0.8238(7) 0.4993(5) 0.3837(3) 0.0489(15) Uani 1 1 d . . . H66 H 0.9193 0.5137 0.3912 0.059 Uiso 1 1 calc R . . C23 C 0.7831(8) 0.4136(5) 0.4038(3) 0.0547(17) Uani 1 1 d . . . H67 H 0.6877 0.3986 0.3974 0.066 Uiso 1 1 calc R . . C24 C 0.8794(7) 0.3416(5) 0.4353(3) 0.0546(17) Uani 1 1 d . . . H23 H 0.8859 0.3505 0.4845 0.065 Uiso 1 1 calc R . . H24 H 0.9719 0.3540 0.4210 0.065 Uiso 1 1 calc R . . C25 C 0.7133(8) 0.3603(4) 0.2435(3) 0.0465(15) Uani 1 1 d . . . C26 C 0.7565(8) 0.4567(4) 0.2236(3) 0.0489(15) Uani 1 1 d . . . H68 H 0.8520 0.4695 0.2226 0.059 Uiso 1 1 calc R . . C27 C 0.7986(7) 0.2168(4) 0.2919(3) 0.0453(14) Uani 1 1 d . . . H25 H 0.6997 0.2065 0.2992 0.054 Uiso 1 1 calc R . . C28 C 0.8885(8) 0.1970(6) 0.3564(3) 0.0586(17) Uani 1 1 d . . . H26 H 0.9829 0.2195 0.3509 0.070 Uiso 1 1 calc R . . H27 H 0.8937 0.1275 0.3626 0.070 Uiso 1 1 calc R . . C29 C 0.8442(8) 0.2406(5) 0.4205(3) 0.0584(18) Uani 1 1 d . . . H28 H 0.7428 0.2340 0.4191 0.070 Uiso 1 1 calc R . . H29 H 0.8852 0.2022 0.4588 0.070 Uiso 1 1 calc R . . C30 C 0.8338(7) 0.1577(5) 0.2342(3) 0.0506(15) Uani 1 1 d . . . H30 H 0.7513 0.1492 0.2025 0.061 Uiso 1 1 calc R . . H31 H 0.8673 0.0957 0.2507 0.061 Uiso 1 1 calc R . . H32 H 0.9057 0.1893 0.2116 0.061 Uiso 1 1 calc R . . C31 C 0.1963(8) 0.4793(5) 0.1468(3) 0.0565(18) Uani 1 1 d . . . H33 H 0.1212 0.5158 0.1205 0.068 Uiso 1 1 calc R . . C32 C 0.142(2) 0.4095(12) 0.1768(6) 0.200(10) Uani 1 1 d . . . H34 H 0.0998 0.3730 0.1378 0.240 Uiso 1 1 calc R . . H35 H 0.0635 0.4415 0.1948 0.240 Uiso 1 1 calc R . . C33 C 0.1703(10) 0.3363(6) 0.2246(5) 0.082(3) Uani 1 1 d . . . H36 H 0.2179 0.2849 0.2026 0.098 Uiso 1 1 calc R . . H37 H 0.0806 0.3107 0.2354 0.098 Uiso 1 1 calc R . . C34 C 0.2563(9) 0.3592(5) 0.2912(5) 0.079(3) Uani 1 1 d . . . H38 H 0.2593 0.3019 0.3198 0.095 Uiso 1 1 calc R . . H69 H 0.3520 0.3727 0.2816 0.095 Uiso 1 1 calc R . . C35 C 0.2076(9) 0.4402(4) 0.3307(3) 0.0593(18) Uani 1 1 d . . . H73 H 0.1111 0.4512 0.3284 0.071 Uiso 1 1 calc R . . C36 C 0.2890(8) 0.4971(4) 0.3683(4) 0.0591(18) Uani 1 1 d . . . H70 H 0.3850 0.4839 0.3734 0.071 Uiso 1 1 calc R . . C37 C 0.2398(7) 0.5805(4) 0.4031(3) 0.0440(14) Uani 1 1 d . . . C38 C 0.3511(8) 0.6475(4) 0.4338(3) 0.0543(17) Uani 1 1 d . . . H39 H 0.4374 0.6350 0.4132 0.065 Uiso 1 1 calc R . . H40 H 0.3690 0.6337 0.4823 0.065 Uiso 1 1 calc R . . C39 C 0.3142(7) 0.7531(4) 0.4248(3) 0.0439(14) Uani 1 1 d . . . H41 H 0.2153 0.7619 0.4305 0.053 Uiso 1 1 calc R . . H42 H 0.3685 0.7902 0.4601 0.053 Uiso 1 1 calc R . . C40 C 0.3426(6) 0.7910(4) 0.3558(3) 0.0361(12) Uani 1 1 d . . . H43 H 0.4421 0.7818 0.3493 0.043 Uiso 1 1 calc R . . C41 C 0.2543(6) 0.7426(4) 0.3010(2) 0.0362(12) Uani 1 1 d . . . H71 H 0.1620 0.7638 0.2908 0.043 Uiso 1 1 calc R . . C42 C 0.2988(7) 0.6711(4) 0.2658(3) 0.0391(13) Uani 1 1 d . . . H72 H 0.3930 0.6528 0.2728 0.047 Uiso 1 1 calc R . . C43 C 0.2046(8) 0.6193(4) 0.2159(3) 0.0457(16) Uani 1 1 d . . . C44 C 0.3536(6) 1.0192(4) 0.2481(2) 0.0358(12) Uani 1 1 d . . . C45 C 0.2024(6) 1.0533(5) 0.2452(3) 0.0472(15) Uani 1 1 d . . . H44 H 0.1402 0.9999 0.2339 0.057 Uiso 1 1 calc R . . H45 H 0.1863 1.1026 0.2109 0.057 Uiso 1 1 calc R . . H46 H 0.1850 1.0791 0.2889 0.057 Uiso 1 1 calc R . . C46 C 0.3579(7) 0.9349(4) 0.1997(3) 0.0434(14) Uani 1 1 d . . . H47 H 0.4502 0.9301 0.1846 0.052 Uiso 1 1 calc R . . H48 H 0.2898 0.9446 0.1609 0.052 Uiso 1 1 calc R . . H49 H 0.3366 0.8764 0.2228 0.052 Uiso 1 1 calc R . . C47 C 0.4411(7) 1.0996(4) 0.2261(3) 0.0503(16) Uani 1 1 d . . . H50 H 0.3982 1.1602 0.2357 0.060 Uiso 1 1 calc R . . H51 H 0.4484 1.0946 0.1778 0.060 Uiso 1 1 calc R . . H52 H 0.5334 1.0962 0.2504 0.060 Uiso 1 1 calc R . . C48 C 0.5926(6) 0.9564(3) 0.3567(3) 0.0356(12) Uani 1 1 d . . . C49 C 0.6828(6) 0.9327(4) 0.3078(3) 0.0386(12) Uani 1 1 d . . . H53 H 0.6468 0.9279 0.2621 0.046 Uiso 1 1 calc R . . C50 C 0.8211(6) 0.9165(4) 0.3252(3) 0.0443(14) Uani 1 1 d . . . H54 H 0.8785 0.9008 0.2913 0.053 Uiso 1 1 calc R . . C51 C 0.8777(7) 0.9225(4) 0.3908(3) 0.0488(15) Uani 1 1 d . . . H55 H 0.9732 0.9111 0.4022 0.059 Uiso 1 1 calc R . . C52 C 0.7924(7) 0.9456(4) 0.4400(3) 0.0509(16) Uani 1 1 d . . . H56 H 0.8301 0.9498 0.4856 0.061 Uiso 1 1 calc R . . C53 C 0.6532(6) 0.9626(4) 0.4232(3) 0.0398(13) Uani 1 1 d . . . H57 H 0.5971 0.9788 0.4576 0.048 Uiso 1 1 calc R . . C54 C 0.3546(6) 1.0760(4) 0.3970(3) 0.0390(13) Uani 1 1 d . . . C55 C 0.4212(7) 1.1622(4) 0.4025(3) 0.0477(15) Uani 1 1 d . . . H58 H 0.4976 1.1737 0.3777 0.057 Uiso 1 1 calc R . . C56 C 0.3774(9) 1.2332(5) 0.4444(4) 0.067(2) Uani 1 1 d . . . H59 H 0.4245 1.2921 0.4477 0.080 Uiso 1 1 calc R . . C57 C 0.2677(10) 1.2187(5) 0.4805(3) 0.067(2) Uani 1 1 d . . . H60 H 0.2389 1.2675 0.5086 0.080 Uiso 1 1 calc R . . C58 C 0.1988(9) 1.1330(6) 0.4761(3) 0.067(2) Uani 1 1 d . . . H61 H 0.1218 1.1226 0.5006 0.080 Uiso 1 1 calc R . . C59 C 0.2444(7) 1.0615(4) 0.4346(3) 0.0505(16) Uani 1 1 d . . . H62 H 0.1988 1.0019 0.4324 0.061 Uiso 1 1 calc R . . C60 C 0.289(2) 0.4423(16) 0.1018(11) 0.216(8) Uiso 1 1 d . . . H74 H 0.2915 0.4854 0.0637 0.259 Uiso 1 1 calc R . . H75 H 0.2559 0.3800 0.0855 0.259 Uiso 1 1 calc R . . H76 H 0.3812 0.4361 0.1255 0.259 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Si1 0.0406(9) 0.0240(7) 0.0328(6) -0.0019(5) 0.0056(6) -0.0059(6) Si2 0.0442(9) 0.0227(6) 0.0336(6) -0.0005(5) -0.0018(6) -0.0014(6) O1 0.056(3) 0.036(2) 0.0363(19) 0.0003(15) 0.0091(17) -0.0081(18) O2 0.045(2) 0.0248(18) 0.047(2) -0.0034(14) 0.0010(17) 0.0032(16) O3 0.077(4) 0.079(4) 0.049(3) -0.003(2) 0.010(2) -0.008(3) O4 0.055(3) 0.043(3) 0.111(4) 0.027(3) 0.005(3) 0.008(2) O5 0.053(3) 0.042(2) 0.050(2) 0.0005(17) 0.0124(19) -0.011(2) O6 0.092(4) 0.054(3) 0.086(3) -0.036(3) -0.051(3) 0.037(3) O7 0.070(4) 0.067(3) 0.066(3) -0.002(2) 0.027(3) -0.003(3) O8 0.066(3) 0.035(2) 0.053(2) -0.0147(17) 0.008(2) 0.0034(19) C1 0.057(4) 0.033(3) 0.060(3) -0.010(3) 0.012(3) -0.013(3) C2 0.055(4) 0.029(3) 0.072(4) -0.006(3) -0.001(3) -0.002(3) C3 0.040(4) 0.031(3) 0.057(3) -0.009(2) -0.003(3) 0.003(2) C4 0.033(3) 0.033(3) 0.031(2) -0.0013(19) 0.004(2) -0.002(2) C5 0.037(4) 0.041(3) 0.079(4) -0.004(3) -0.008(3) -0.005(3) C6 0.045(4) 0.032(3) 0.074(4) -0.007(3) -0.008(3) 0.002(3) C7 0.055(4) 0.040(3) 0.039(3) -0.007(2) 0.012(3) -0.002(3) C8 0.044(4) 0.034(3) 0.034(3) -0.008(2) 0.009(2) -0.007(2) C9 0.046(4) 0.045(3) 0.047(3) -0.006(2) 0.004(3) 0.005(3) C10 0.062(4) 0.024(3) 0.045(3) -0.010(2) 0.007(3) -0.003(2) C11 0.034(5) 0.109(8) 0.169(10) 0.053(7) 0.030(5) 0.002(5) C12 0.070(6) 0.078(6) 0.087(5) 0.031(4) 0.021(4) 0.001(4) C13 0.049(5) 0.069(5) 0.123(7) 0.021(5) -0.008(5) 0.003(4) C14 0.033(3) 0.027(3) 0.050(3) -0.007(2) 0.004(2) -0.005(2) C15 0.059(4) 0.045(3) 0.047(3) 0.001(2) -0.003(3) -0.002(3) C16 0.067(5) 0.045(4) 0.072(4) -0.008(3) -0.017(4) 0.008(3) C17 0.073(5) 0.037(3) 0.042(3) -0.007(2) 0.006(3) 0.007(3) C18 0.070(5) 0.045(3) 0.039(3) -0.011(2) 0.002(3) -0.009(3) C19 0.063(4) 0.029(3) 0.030(3) -0.001(2) 0.001(2) -0.006(3) C20 0.083(5) 0.038(3) 0.030(3) 0.002(2) 0.013(3) -0.007(3) C21 0.028(3) 0.048(3) 0.030(2) -0.009(2) 0.007(2) -0.003(2) C22 0.046(4) 0.059(4) 0.041(3) -0.005(3) 0.005(3) -0.006(3) C23 0.082(5) 0.051(4) 0.034(3) -0.008(2) 0.019(3) -0.020(3) C24 0.052(4) 0.068(4) 0.044(3) 0.010(3) 0.004(3) -0.007(3) C25 0.055(5) 0.036(3) 0.053(3) -0.001(2) 0.022(3) -0.008(3) C26 0.065(5) 0.041(3) 0.045(3) -0.004(2) 0.021(3) 0.003(3) C27 0.052(4) 0.037(3) 0.047(3) -0.001(2) 0.007(3) -0.010(3) C28 0.059(5) 0.065(4) 0.051(3) 0.007(3) 0.003(3) -0.002(3) C29 0.072(5) 0.061(4) 0.041(3) 0.007(3) 0.002(3) -0.009(3) C30 0.060(5) 0.044(4) 0.048(3) 0.002(3) 0.005(3) 0.000(3) C31 0.075(5) 0.041(3) 0.050(3) -0.017(3) -0.016(3) 0.019(3) C32 0.31(2) 0.198(16) 0.089(8) -0.040(9) 0.019(10) -0.209(16) C33 0.088(7) 0.046(4) 0.114(7) -0.017(4) 0.022(5) -0.008(4) C34 0.069(6) 0.035(4) 0.128(7) -0.028(4) -0.010(5) 0.004(3) C35 0.087(6) 0.034(3) 0.059(4) 0.008(3) 0.014(4) -0.002(3) C36 0.074(5) 0.025(3) 0.081(5) -0.006(3) 0.017(4) 0.001(3) C37 0.058(4) 0.035(3) 0.041(3) 0.005(2) 0.010(3) -0.008(3) C38 0.083(5) 0.038(3) 0.039(3) 0.003(2) -0.005(3) 0.002(3) C39 0.063(4) 0.033(3) 0.034(3) -0.002(2) -0.003(2) -0.003(3) C40 0.039(3) 0.024(3) 0.045(3) -0.007(2) 0.004(2) 0.003(2) C41 0.050(4) 0.025(2) 0.033(2) 0.0058(19) 0.001(2) 0.004(2) C42 0.051(4) 0.026(3) 0.043(3) -0.003(2) 0.016(2) -0.005(2) C43 0.082(5) 0.020(3) 0.034(3) -0.001(2) 0.002(3) 0.004(3) C44 0.046(4) 0.025(2) 0.034(3) 0.0004(19) -0.004(2) -0.001(2) C45 0.044(4) 0.054(4) 0.040(3) 0.007(2) -0.012(3) 0.003(3) C46 0.055(4) 0.042(3) 0.032(3) -0.004(2) -0.004(2) -0.008(3) C47 0.068(5) 0.033(3) 0.047(3) 0.009(2) -0.009(3) -0.008(3) C48 0.045(4) 0.020(2) 0.041(3) -0.0010(18) 0.000(2) -0.006(2) C49 0.048(4) 0.025(3) 0.042(3) 0.002(2) 0.002(2) 0.000(2) C50 0.045(4) 0.031(3) 0.057(3) 0.002(2) 0.004(3) -0.004(3) C51 0.042(4) 0.027(3) 0.073(4) -0.003(3) -0.015(3) 0.001(2) C52 0.059(5) 0.038(3) 0.051(3) 0.002(3) -0.017(3) 0.000(3) C53 0.044(4) 0.033(3) 0.041(3) 0.002(2) -0.004(2) 0.004(2) C54 0.045(4) 0.035(3) 0.034(3) 0.002(2) -0.007(2) 0.007(2) C55 0.043(4) 0.035(3) 0.061(4) -0.007(3) -0.012(3) 0.003(3) C56 0.086(6) 0.037(4) 0.070(4) -0.017(3) -0.024(4) 0.013(3) C57 0.114(7) 0.040(4) 0.042(3) -0.015(3) -0.015(4) 0.034(4) C58 0.094(6) 0.067(5) 0.042(3) 0.009(3) 0.015(3) 0.032(4) C59 0.071(5) 0.033(3) 0.047(3) 0.002(2) 0.006(3) 0.011(3) _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 Si1 O1 1.635(4) . ? Si1 C14 1.878(6) . ? Si1 C4 1.881(5) . ? Si1 C8 1.908(5) . ? Si2 O2 1.643(4) . ? Si2 C48 1.867(6) . ? Si2 C54 1.883(6) . ? Si2 C44 1.893(5) . ? O1 C19 1.431(7) . ? O2 C40 1.430(6) . ? O3 C21 1.232(7) . ? O4 C25 1.223(8) . ? O5 C25 1.303(8) . ? O5 C27 1.451(7) . ? O6 C43 1.183(8) . ? O7 C37 1.226(8) . ? O8 C43 1.355(7) . ? O8 C31 1.462(7) . ? C1 C2 1.365(9) . ? C1 C5 1.381(9) . ? C2 C3 1.390(8) . ? C3 C4 1.382(8) . ? C4 C6 1.386(8) . ? C5 C6 1.376(9) . ? C7 C8 1.542(7) . ? C8 C9 1.509(8) . ? C8 C10 1.539(7) . ? C11 C13 1.350(14) . ? C11 C12 1.411(12) . ? C12 C14 1.392(9) . ? C13 C16 1.362(12) . ? C14 C15 1.394(8) . ? C15 C16 1.414(10) . ? C17 C18 1.526(9) . ? C17 C19 1.524(7) . ? C18 C21 1.490(8) . ? C19 C20 1.503(8) . ? C20 C26 1.293(9) . ? C21 C22 1.454(9) . ? C22 C23 1.348(9) . ? C23 C24 1.481(10) . ? C24 C29 1.489(10) . ? C25 C26 1.492(8) . ? C27 C30 1.495(8) . ? C27 C28 1.512(9) . ? C28 C29 1.527(9) . ? C31 C32 1.294(14) . ? C31 C60 1.44(2) . ? C32 C33 1.418(19) . ? C33 C34 1.538(13) . ? C34 C35 1.496(10) . ? C35 C36 1.312(10) . ? C36 C37 1.473(9) . ? C37 C38 1.522(9) . ? C38 C39 1.541(8) . ? C39 C40 1.535(7) . ? C40 C41 1.491(7) . ? C41 C42 1.330(7) . ? C42 C43 1.480(8) . ? C44 C47 1.514(8) . ? C44 C46 1.539(7) . ? C44 C45 1.546(8) . ? C48 C53 1.406(7) . ? C48 C49 1.421(8) . ? C49 C50 1.376(9) . ? C50 C51 1.375(9) . ? C51 C52 1.393(10) . ? C52 C53 1.386(9) . ? C54 C55 1.380(8) . ? C54 C59 1.389(9) . ? C55 C56 1.402(9) . ? C56 C57 1.366(12) . ? C57 C58 1.383(12) . ? C58 C59 1.409(9) . ? 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 Si1 C14 102.0(2) . . ? O1 Si1 C4 110.6(2) . . ? C14 Si1 C4 109.0(2) . . ? O1 Si1 C8 111.0(2) . . ? C14 Si1 C8 111.7(2) . . ? C4 Si1 C8 112.1(2) . . ? O2 Si2 C48 111.5(2) . . ? O2 Si2 C54 104.0(2) . . ? C48 Si2 C54 108.6(2) . . ? O2 Si2 C44 108.8(2) . . ? C48 Si2 C44 113.7(3) . . ? C54 Si2 C44 109.8(2) . . ? C19 O1 Si1 129.3(4) . . ? C40 O2 Si2 130.1(4) . . ? C25 O5 C27 118.0(5) . . ? C43 O8 C31 117.6(5) . . ? C2 C1 C5 119.0(5) . . ? C1 C2 C3 120.0(6) . . ? C4 C3 C2 121.9(6) . . ? C3 C4 C6 116.9(5) . . ? C3 C4 Si1 120.5(4) . . ? C6 C4 Si1 122.6(4) . . ? C6 C5 C1 120.7(6) . . ? C5 C6 C4 121.4(6) . . ? C9 C8 C7 108.6(5) . . ? C9 C8 C10 108.5(5) . . ? C7 C8 C10 109.2(4) . . ? C9 C8 Si1 113.3(4) . . ? C7 C8 Si1 110.4(4) . . ? C10 C8 Si1 106.9(4) . . ? C13 C11 C12 118.8(8) . . ? C14 C12 C11 122.0(8) . . ? C11 C13 C16 121.8(8) . . ? C12 C14 C15 117.0(6) . . ? C12 C14 Si1 119.7(5) . . ? C15 C14 Si1 123.3(5) . . ? C14 C15 C16 120.8(6) . . ? C13 C16 C15 119.5(7) . . ? C18 C17 C19 112.6(5) . . ? C21 C18 C17 114.9(5) . . ? O1 C19 C20 105.7(5) . . ? O1 C19 C17 108.2(5) . . ? C20 C19 C17 113.0(5) . . ? C26 C20 C19 122.8(7) . . ? O3 C21 C22 120.9(6) . . ? O3 C21 C18 118.6(6) . . ? C22 C21 C18 120.5(5) . . ? C23 C22 C21 125.4(6) . . ? C22 C23 C24 123.5(7) . . ? C23 C24 C29 116.7(6) . . ? O4 C25 O5 125.3(5) . . ? O4 C25 C26 124.6(6) . . ? O5 C25 C26 110.1(6) . . ? C20 C26 C25 122.3(7) . . ? O5 C27 C30 106.8(5) . . ? O5 C27 C28 108.3(5) . . ? C30 C27 C28 113.6(6) . . ? C27 C28 C29 117.1(6) . . ? C24 C29 C28 118.3(6) . . ? C32 C31 O8 111.3(7) . . ? C32 C31 C60 108.9(14) . . ? O8 C31 C60 109.3(10) . . ? C31 C32 C33 144.1(16) . . ? C32 C33 C34 119.0(8) . . ? C35 C34 C33 116.5(7) . . ? C36 C35 C34 124.5(8) . . ? C35 C36 C37 123.7(7) . . ? O7 C37 C36 124.6(6) . . ? O7 C37 C38 119.6(6) . . ? C36 C37 C38 115.8(6) . . ? C37 C38 C39 114.0(6) . . ? C40 C39 C38 112.5(5) . . ? O2 C40 C41 109.2(4) . . ? O2 C40 C39 106.9(4) . . ? C41 C40 C39 111.2(5) . . ? C42 C41 C40 123.0(5) . . ? C41 C42 C43 121.4(6) . . ? O6 C43 O8 124.9(5) . . ? O6 C43 C42 126.6(5) . . ? O8 C43 C42 108.4(6) . . ? C47 C44 C46 110.1(5) . . ? C47 C44 C45 108.5(5) . . ? C46 C44 C45 107.8(5) . . ? C47 C44 Si2 112.8(4) . . ? C46 C44 Si2 111.1(4) . . ? C45 C44 Si2 106.3(4) . . ? C53 C48 C49 116.0(5) . . ? C53 C48 Si2 119.3(4) . . ? C49 C48 Si2 124.7(4) . . ? C50 C49 C48 121.6(5) . . ? C51 C50 C49 121.3(6) . . ? C50 C51 C52 118.8(6) . . ? C53 C52 C51 120.5(5) . . ? C52 C53 C48 121.8(6) . . ? C55 C54 C59 118.0(5) . . ? C55 C54 Si2 121.8(5) . . ? C59 C54 Si2 120.1(4) . . ? C54 C55 C56 120.6(7) . . ? C57 C56 C55 120.9(7) . . ? C56 C57 C58 119.8(6) . . ? C57 C58 C59 119.1(7) . . ? C54 C59 C58 121.5(6) . . ? _diffrn_measured_fraction_theta_max 0.922 _diffrn_reflns_theta_full 66.59 _diffrn_measured_fraction_theta_full 0.922 _refine_diff_density_max 1.077 _refine_diff_density_min -0.473 _refine_diff_density_rms 0.077 # Attachment '- (f)-Compound 6.cif' data__AD02 _database_code_depnum_ccdc_archive 'CCDC 820818' #TrackingRef '- (f)-Compound 6.cif' _audit_creation_date 2009-12-16 _audit_creation_method 'by CrystalStructure 3.8' _audit_update_record ? #============================================================================== # CHEMICAL DATA _chemical_formula_sum 'C14 H20 O4 ' _chemical_formula_moiety 'C14 H20 O4 ' _chemical_formula_weight 252.31 _chemical_melting_point ? #============================================================================== # CRYSTAL DATA _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' _symmetry_space_group_name_Hall 'P 2ac 2ab' _symmetry_Int_Tables_number 19 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 +X,+Y,+Z 2 1/2+X,1/2-Y,-Z 3 -X,1/2+Y,1/2-Z 4 1/2-X,-Y,1/2+Z #------------------------------------------------------------------------------ _cell_length_a 7.2838(7) _cell_length_b 9.5550(9) _cell_length_c 19.3652(19) _cell_angle_alpha 90.0000 _cell_angle_beta 90.0000 _cell_angle_gamma 90.0000 _cell_volume 1347.8(2) _cell_formula_units_Z 4 _cell_measurement_reflns_used 11789 _cell_measurement_theta_min 3.0 _cell_measurement_theta_max 27.6 _cell_measurement_temperature 223.1 #------------------------------------------------------------------------------ _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.08 _exptl_crystal_density_diffrn 1.243 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 544.00 _exptl_absorpt_coefficient_mu 0.090 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _exptl_absorpt_correction_T_min 0.738 _exptl_absorpt_correction_T_max 0.993 #============================================================================== # EXPERIMENTAL DATA _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71075 _diffrn_measurement_device_type 'Rigaku SCXmini' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 6.85 _diffrn_reflns_number 13934 _diffrn_reflns_av_R_equivalents 0.066 _diffrn_reflns_theta_max 27.48 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.998 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 #============================================================================== # 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 3088 _reflns_number_gt 2230 _reflns_threshold_expression F^2^>2.0\s(F^2^) _refine_ls_structure_factor_coef Fsqd _refine_ls_R_factor_gt 0.0606 _refine_ls_wR_factor_ref 0.1412 _refine_ls_hydrogen_treatment refall _refine_ls_number_reflns 3088 _refine_ls_number_parameters 168 _refine_ls_goodness_of_fit_ref 1.076 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.0611P)^2^+0.1034P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_shift/su_max 0.0000 _refine_diff_density_max 0.19 _refine_diff_density_min -0.18 _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack, H. D. (1983), Acta Cryst. A39, 876-881. 1293 Friedel Pairs' _refine_ls_abs_structure_Flack -1.8(16) _chemical_absolute_configuration ad loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source O O 0.011 0.006 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; C C 0.003 0.002 ; 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) ; #============================================================================== # 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 0.4064(2) 0.58237(17) 0.90649(8) 0.0434(4) Uani 1.00 1 d . . . O(2) O 0.4752(2) 0.81168(18) 0.90785(9) 0.0537(5) Uani 1.00 1 d . . . O(3) O 0.4874(3) 0.5673(2) 0.66579(9) 0.0634(5) Uani 1.00 1 d . . . O(4) O 1.0204(3) 0.7820(2) 0.83365(11) 0.0824(7) Uani 1.00 1 d . . . C(1) C 0.4516(3) 0.7032(2) 0.87639(13) 0.0423(6) Uani 1.00 1 d . . . C(2) C 0.4723(3) 0.6883(2) 0.79992(12) 0.0467(6) Uani 1.00 1 d . . . C(3) C 0.6197(3) 0.5789(2) 0.78060(11) 0.0353(5) Uani 1.00 1 d . . . C(4) C 0.6568(3) 0.5793(2) 0.70208(11) 0.0453(6) Uani 1.00 1 d . . . C(5) C 0.7582(4) 0.7117(2) 0.67970(12) 0.0543(7) Uani 1.00 1 d . . . C(6) C 0.9390(4) 0.7289(3) 0.71800(14) 0.0694(9) Uani 1.00 1 d . . . C(7) C 0.9226(3) 0.7139(3) 0.79542(13) 0.0509(7) Uani 1.00 1 d . . . C(8) C 0.7944(3) 0.6036(2) 0.82144(11) 0.0362(5) Uani 1.00 1 d . . . C(9) C 0.8451(3) 0.5327(3) 0.87776(12) 0.0463(6) Uani 1.00 1 d . . . C(10) C 0.7516(4) 0.4118(2) 0.91195(12) 0.0493(6) Uani 1.00 1 d . . . C(11) C 0.7156(4) 0.4356(2) 0.98955(12) 0.0499(6) Uani 1.00 1 d . . . C(12) C 0.6072(3) 0.5667(2) 1.00736(12) 0.0471(6) Uani 1.00 1 d . . . C(13) C 0.4107(3) 0.5757(2) 0.98268(12) 0.0456(6) Uani 1.00 1 d . . . C(14) C 0.2923(4) 0.4542(3) 1.00244(16) 0.0744(9) Uani 1.00 1 d . . . H(1) H 0.5061 0.7791 0.7801 0.056 Uiso 1.00 1 c R . . H(2) H 0.3543 0.6603 0.7799 0.056 Uiso 1.00 1 c R . . H(3) H 0.5719 0.4854 0.7932 0.042 Uiso 1.00 1 c R . . H(4) H 0.7340 0.4973 0.6906 0.054 Uiso 1.00 1 c R . . H(5) H 0.7821 0.7075 0.6300 0.065 Uiso 1.00 1 c R . . H(6) H 0.6803 0.7934 0.6886 0.065 Uiso 1.00 1 c R . . H(7) H 1.0260 0.6588 0.7009 0.083 Uiso 1.00 1 c R . . H(8) H 0.9896 0.8215 0.7075 0.083 Uiso 1.00 1 c R . . H(9) H 0.9545 0.5628 0.8988 0.056 Uiso 1.00 1 c R . . H(10) H 0.8277 0.3280 0.9063 0.059 Uiso 1.00 1 c R . . H(11) H 0.6342 0.3945 0.8887 0.059 Uiso 1.00 1 c R . . H(12) H 0.6492 0.3543 1.0076 0.060 Uiso 1.00 1 c R . . H(13) H 0.8341 0.4399 1.0134 0.060 Uiso 1.00 1 c R . . H(14) H 0.6068 0.5766 1.0577 0.057 Uiso 1.00 1 c R . . H(15) H 0.6737 0.6473 0.9886 0.057 Uiso 1.00 1 c R . . H(16) H 0.3550 0.6623 1.0013 0.055 Uiso 1.00 1 c R . . H(17) H 0.1664 0.4855 1.0079 0.089 Uiso 1.00 1 c R . . H(18) H 0.3357 0.4148 1.0456 0.089 Uiso 1.00 1 c R . . H(19) H 0.2978 0.3835 0.9666 0.089 Uiso 1.00 1 c R . . H(3A) H 0.496(5) 0.487(3) 0.6406(18) 0.087(11) Uiso 1.00 1 c . . . 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) 0.0454(9) 0.0423(9) 0.0425(9) 0.0037(8) 0.0039(7) 0.0055(7) O(2) 0.0760(13) 0.0393(9) 0.0459(9) 0.0098(10) 0.0080(9) 0.0026(8) O(3) 0.0810(14) 0.0621(13) 0.0471(10) 0.0122(11) -0.0261(11) -0.0179(10) O(4) 0.0799(15) 0.1082(18) 0.0590(13) -0.0501(15) -0.0014(12) -0.0052(12) C(1) 0.0415(14) 0.0444(14) 0.0409(13) 0.0131(11) 0.0040(11) 0.0069(12) C(2) 0.0535(16) 0.0490(15) 0.0375(13) 0.0137(13) -0.0016(12) 0.0052(11) C(3) 0.0461(13) 0.0285(11) 0.0314(11) 0.0005(11) -0.0036(10) -0.0014(9) C(4) 0.0616(16) 0.0423(14) 0.0321(12) 0.0105(14) -0.0082(12) -0.0068(11) C(5) 0.083(2) 0.0515(15) 0.0283(11) -0.0014(15) 0.0079(13) 0.0035(12) C(6) 0.082(2) 0.084(2) 0.0424(15) -0.0221(19) 0.0131(15) 0.0044(15) C(7) 0.0505(16) 0.0643(18) 0.0378(13) -0.0129(14) 0.0040(13) -0.0027(13) C(8) 0.0417(12) 0.0412(13) 0.0257(10) -0.0000(11) 0.0047(10) -0.0046(10) C(9) 0.0374(13) 0.0672(17) 0.0344(12) 0.0063(12) 0.0022(10) 0.0051(12) C(10) 0.0619(17) 0.0497(14) 0.0363(12) 0.0207(14) 0.0040(12) 0.0098(11) C(11) 0.0497(15) 0.0654(17) 0.0347(12) 0.0104(14) 0.0003(11) 0.0112(13) C(12) 0.0628(17) 0.0506(15) 0.0280(11) -0.0098(14) 0.0034(11) -0.0015(12) C(13) 0.0577(16) 0.0422(14) 0.0370(12) 0.0086(13) 0.0153(12) 0.0053(11) C(14) 0.0523(17) 0.095(2) 0.076(2) -0.0057(17) 0.0062(16) 0.033(2) #============================================================================== _computing_data_collection PROCESS-AUTO _computing_cell_refinement PROCESS-AUTO _computing_data_reduction CrystalStructure _computing_structure_solution SHELXS97 _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(1) 1.335(3) yes . . O(1) C(13) 1.477(2) yes . . O(2) C(1) 1.214(3) yes . . O(3) C(4) 1.425(3) yes . . O(4) C(7) 1.216(3) yes . . C(1) C(2) 1.495(3) yes . . C(2) C(3) 1.544(3) yes . . C(3) C(4) 1.544(3) yes . . C(3) C(8) 1.516(3) yes . . C(4) C(5) 1.528(3) yes . . C(5) C(6) 1.520(4) yes . . C(6) C(7) 1.511(3) yes . . C(7) C(8) 1.496(3) yes . . C(8) C(9) 1.336(3) yes . . C(9) C(10) 1.495(3) yes . . C(10) C(11) 1.542(3) yes . . C(11) C(12) 1.521(3) yes . . C(12) C(13) 1.511(3) yes . . C(13) C(14) 1.496(4) yes . . O(3) H(3A) 0.92(3) no . . C(2) H(1) 0.980 no . . C(2) H(2) 0.980 no . . C(3) H(3) 0.990 no . . C(4) H(4) 0.990 no . . C(5) H(5) 0.980 no . . C(5) H(6) 0.980 no . . C(6) H(7) 0.980 no . . C(6) H(8) 0.980 no . . C(9) H(9) 0.940 no . . C(10) H(10) 0.980 no . . C(10) H(11) 0.980 no . . C(11) H(12) 0.980 no . . C(11) H(13) 0.980 no . . C(12) H(14) 0.980 no . . C(12) H(15) 0.980 no . . C(13) H(16) 0.990 no . . C(14) H(17) 0.970 no . . C(14) H(18) 0.970 no . . C(14) H(19) 0.970 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(1) O(1) C(13) 117.94(18) yes . . . O(1) C(1) O(2) 123.7(2) yes . . . O(1) C(1) C(2) 112.0(2) yes . . . O(2) C(1) C(2) 124.3(2) yes . . . C(1) C(2) C(3) 112.0(2) yes . . . C(2) C(3) C(4) 111.02(18) yes . . . C(2) C(3) C(8) 110.59(18) yes . . . C(4) C(3) C(8) 111.49(19) yes . . . O(3) C(4) C(3) 109.5(2) yes . . . O(3) C(4) C(5) 110.2(2) yes . . . C(3) C(4) C(5) 111.45(19) yes . . . C(4) C(5) C(6) 111.7(2) yes . . . C(5) C(6) C(7) 113.9(2) yes . . . O(4) C(7) C(6) 120.5(2) yes . . . O(4) C(7) C(8) 122.5(2) yes . . . C(6) C(7) C(8) 116.8(2) yes . . . C(3) C(8) C(7) 117.24(19) yes . . . C(3) C(8) C(9) 125.4(2) yes . . . C(7) C(8) C(9) 117.4(2) yes . . . C(8) C(9) C(10) 128.9(2) yes . . . C(9) C(10) C(11) 113.3(2) yes . . . C(10) C(11) C(12) 115.5(2) yes . . . C(11) C(12) C(13) 117.8(2) yes . . . O(1) C(13) C(12) 109.77(19) yes . . . O(1) C(13) C(14) 106.1(2) yes . . . C(12) C(13) C(14) 114.9(2) yes . . . C(4) O(3) H(3A) 106(2) no . . . C(1) C(2) H(1) 109.2 no . . . C(1) C(2) H(2) 109.2 no . . . C(3) C(2) H(1) 109.2 no . . . C(3) C(2) H(2) 109.2 no . . . H(1) C(2) H(2) 107.9 no . . . C(2) C(3) H(3) 107.9 no . . . C(4) C(3) H(3) 107.9 no . . . C(8) C(3) H(3) 107.9 no . . . O(3) C(4) H(4) 108.5 no . . . C(3) C(4) H(4) 108.5 no . . . C(5) C(4) H(4) 108.5 no . . . C(4) C(5) H(5) 109.3 no . . . C(4) C(5) H(6) 109.3 no . . . C(6) C(5) H(5) 109.3 no . . . C(6) C(5) H(6) 109.3 no . . . H(5) C(5) H(6) 107.9 no . . . C(5) C(6) H(7) 108.8 no . . . C(5) C(6) H(8) 108.8 no . . . C(7) C(6) H(7) 108.8 no . . . C(7) C(6) H(8) 108.8 no . . . H(7) C(6) H(8) 107.7 no . . . C(8) C(9) H(9) 115.6 no . . . C(10) C(9) H(9) 115.6 no . . . C(9) C(10) H(10) 108.9 no . . . C(9) C(10) H(11) 108.9 no . . . C(11) C(10) H(10) 108.9 no . . . C(11) C(10) H(11) 108.9 no . . . H(10) C(10) H(11) 107.7 no . . . C(10) C(11) H(12) 108.4 no . . . C(10) C(11) H(13) 108.4 no . . . C(12) C(11) H(12) 108.4 no . . . C(12) C(11) H(13) 108.4 no . . . H(12) C(11) H(13) 107.5 no . . . C(11) C(12) H(14) 107.9 no . . . C(11) C(12) H(15) 107.9 no . . . C(13) C(12) H(14) 107.9 no . . . C(13) C(12) H(15) 107.9 no . . . H(14) C(12) H(15) 107.2 no . . . O(1) C(13) H(16) 108.6 no . . . C(12) C(13) H(16) 108.6 no . . . C(14) C(13) H(16) 108.6 no . . . C(13) C(14) H(17) 109.5 no . . . C(13) C(14) H(18) 109.5 no . . . C(13) C(14) H(19) 109.5 no . . . H(17) C(14) H(18) 109.5 no . . . H(17) C(14) H(19) 109.5 no . . . H(18) C(14) H(19) 109.5 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(1) O(1) C(13) C(12) -75.7(2) ? . . . . C(1) O(1) C(13) C(14) 159.6(2) ? . . . . C(13) O(1) C(1) O(2) -8.8(3) ? . . . . C(13) O(1) C(1) C(2) 170.3(2) ? . . . . O(1) C(1) C(2) C(3) -58.5(2) ? . . . . O(2) C(1) C(2) C(3) 120.6(2) ? . . . . C(1) C(2) C(3) C(4) -172.5(2) ? . . . . C(1) C(2) C(3) C(8) -48.2(2) ? . . . . C(2) C(3) C(4) O(3) -51.5(2) ? . . . . C(2) C(3) C(4) C(5) 70.7(2) ? . . . . C(2) C(3) C(8) C(7) -81.6(2) ? . . . . C(2) C(3) C(8) C(9) 100.1(2) ? . . . . C(4) C(3) C(8) C(7) 42.5(2) ? . . . . C(4) C(3) C(8) C(9) -135.8(2) ? . . . . C(8) C(3) C(4) O(3) -175.27(19) ? . . . . C(8) C(3) C(4) C(5) -53.1(2) ? . . . . O(3) C(4) C(5) C(6) 179.4(2) ? . . . . C(3) C(4) C(5) C(6) 57.6(2) ? . . . . C(4) C(5) C(6) C(7) -49.8(3) ? . . . . C(5) C(6) C(7) O(4) -146.5(2) ? . . . . C(5) C(6) C(7) C(8) 38.9(3) ? . . . . O(4) C(7) C(8) C(3) 149.6(2) ? . . . . O(4) C(7) C(8) C(9) -32.0(3) ? . . . . C(6) C(7) C(8) C(3) -35.9(3) ? . . . . C(6) C(7) C(8) C(9) 142.5(2) ? . . . . C(3) C(8) C(9) C(10) 2.8(4) ? . . . . C(7) C(8) C(9) C(10) -175.5(2) ? . . . . C(8) C(9) C(10) C(11) -126.5(2) ? . . . . C(9) C(10) C(11) C(12) 55.5(3) ? . . . . C(10) C(11) C(12) C(13) 64.8(3) ? . . . . C(11) C(12) C(13) O(1) -66.1(2) ? . . . . C(11) C(12) C(13) C(14) 53.4(3) ? . . . . 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(2) O(3) 2.841(2) ? . 3_656 O(2) C(4) 3.464(3) ? . 3_656 O(2) C(12) 3.351(3) ? . 2_467 O(3) O(2) 2.841(2) ? . 3_646 O(4) C(1) 3.334(3) ? . 1_655 O(4) C(2) 3.473(3) ? . 1_655 O(4) C(12) 3.460(3) ? . 2_567 C(1) O(4) 3.334(3) ? . 1_455 C(2) O(4) 3.473(3) ? . 1_455 C(4) O(2) 3.464(3) ? . 3_646 C(12) O(2) 3.351(3) ? . 2_567 C(12) O(4) 3.460(3) ? . 2_467 O(1) H(6) 3.378 ? . 3_646 O(1) H(9) 3.300 ? . 1_455 O(2) H(4) 3.017 ? . 3_656 O(2) H(13) 3.002 ? . 2_467 O(2) H(14) 2.964 ? . 2_467 O(2) H(15) 3.000 ? . 2_467 O(2) H(16) 3.288 ? . 2_567 O(2) H(17) 2.890 ? . 2_567 O(2) H(3A) 1.93(3) ? . 3_656 O(3) H(1) 2.947 ? . 3_646 O(3) H(7) 3.538 ? . 1_455 O(3) H(11) 3.417 ? . 3_656 O(3) H(13) 3.226 ? . 4_664 O(3) H(17) 3.294 ? . 4_564 O(3) H(18) 3.314 ? . 4_564 O(4) H(2) 2.890 ? . 1_655 O(4) H(4) 2.766 ? . 3_756 O(4) H(14) 2.578 ? . 2_567 O(4) H(16) 3.456 ? . 2_567 C(1) H(4) 3.377 ? . 3_656 C(1) H(14) 3.516 ? . 2_467 C(1) H(3A) 2.75(3) ? . 3_656 C(2) H(3) 3.378 ? . 3_656 C(2) H(4) 3.318 ? . 3_656 C(2) H(3A) 3.08(3) ? . 3_656 C(3) H(1) 3.230 ? . 3_646 C(3) H(6) 3.546 ? . 3_646 C(4) H(1) 3.124 ? . 3_646 C(5) H(3) 3.591 ? . 3_656 C(5) H(12) 3.457 ? . 4_664 C(5) H(13) 3.595 ? . 4_664 C(5) H(19) 3.299 ? . 3_656 C(6) H(2) 3.320 ? . 1_655 C(6) H(10) 3.096 ? . 3_756 C(7) H(2) 3.200 ? . 1_655 C(8) H(8) 3.171 ? . 3_746 C(9) H(8) 2.871 ? . 3_746 C(9) H(17) 3.470 ? . 1_655 C(10) H(8) 3.106 ? . 3_746 C(10) H(18) 3.285 ? . 2_557 C(11) H(5) 3.043 ? . 4_665 C(11) H(17) 3.337 ? . 1_655 C(11) H(18) 3.527 ? . 2_557 C(11) H(19) 3.221 ? . 2_557 C(12) H(16) 3.161 ? . 2_567 C(13) H(15) 3.208 ? . 2_467 C(14) H(5) 3.525 ? . 3_646 C(14) H(9) 3.341 ? . 1_455 C(14) H(10) 3.234 ? . 2_457 C(14) H(12) 3.132 ? . 2_457 C(14) H(13) 3.346 ? . 1_455 C(14) H(3A) 3.45(3) ? . 4_565 H(1) O(3) 2.947 ? . 3_656 H(1) C(3) 3.230 ? . 3_656 H(1) C(4) 3.124 ? . 3_656 H(1) H(3) 2.495 ? . 3_656 H(1) H(4) 2.780 ? . 3_656 H(1) H(11) 3.598 ? . 3_656 H(1) H(3A) 2.507 ? . 3_656 H(2) O(4) 2.890 ? . 1_455 H(2) C(6) 3.320 ? . 1_455 H(2) C(7) 3.200 ? . 1_455 H(2) H(3) 3.456 ? . 3_656 H(2) H(4) 3.333 ? . 3_656 H(2) H(6) 3.567 ? . 3_646 H(2) H(7) 2.839 ? . 1_455 H(2) H(8) 3.376 ? . 1_455 H(3) C(2) 3.378 ? . 3_646 H(3) C(5) 3.591 ? . 3_646 H(3) H(1) 2.495 ? . 3_646 H(3) H(2) 3.456 ? . 3_646 H(3) H(6) 2.620 ? . 3_646 H(3) H(8) 3.557 ? . 3_746 H(4) O(2) 3.017 ? . 3_646 H(4) O(4) 2.766 ? . 3_746 H(4) C(1) 3.377 ? . 3_646 H(4) C(2) 3.318 ? . 3_646 H(4) H(1) 2.780 ? . 3_646 H(4) H(2) 3.333 ? . 3_646 H(4) H(8) 3.281 ? . 3_746 H(4) H(13) 3.520 ? . 4_664 H(4) H(14) 2.910 ? . 4_664 H(5) C(11) 3.043 ? . 4_664 H(5) C(14) 3.525 ? . 3_656 H(5) H(10) 3.146 ? . 3_756 H(5) H(11) 3.538 ? . 3_656 H(5) H(12) 2.492 ? . 4_664 H(5) H(13) 2.792 ? . 4_664 H(5) H(14) 3.159 ? . 4_664 H(5) H(18) 3.432 ? . 4_664 H(5) H(19) 2.581 ? . 3_656 H(6) O(1) 3.378 ? . 3_656 H(6) C(3) 3.546 ? . 3_656 H(6) H(2) 3.567 ? . 3_656 H(6) H(3) 2.620 ? . 3_656 H(6) H(11) 2.902 ? . 3_656 H(6) H(19) 3.129 ? . 3_656 H(7) O(3) 3.538 ? . 1_655 H(7) H(2) 2.839 ? . 1_655 H(7) H(10) 2.839 ? . 3_756 H(7) H(18) 3.248 ? . 4_664 H(8) C(8) 3.171 ? . 3_756 H(8) C(9) 2.871 ? . 3_756 H(8) C(10) 3.106 ? . 3_756 H(8) H(2) 3.376 ? . 1_655 H(8) H(3) 3.557 ? . 3_756 H(8) H(4) 3.281 ? . 3_756 H(8) H(9) 3.117 ? . 3_756 H(8) H(10) 2.576 ? . 3_756 H(8) H(11) 3.386 ? . 3_756 H(9) O(1) 3.300 ? . 1_655 H(9) C(14) 3.341 ? . 1_655 H(9) H(8) 3.117 ? . 3_746 H(9) H(16) 3.342 ? . 2_567 H(9) H(17) 2.720 ? . 1_655 H(9) H(19) 3.304 ? . 1_655 H(10) C(6) 3.096 ? . 3_746 H(10) C(14) 3.234 ? . 2_557 H(10) H(5) 3.146 ? . 3_746 H(10) H(7) 2.839 ? . 3_746 H(10) H(8) 2.576 ? . 3_746 H(10) H(12) 3.360 ? . 2_557 H(10) H(17) 3.496 ? . 1_655 H(10) H(18) 2.501 ? . 2_557 H(10) H(19) 3.192 ? . 2_557 H(11) O(3) 3.417 ? . 3_646 H(11) H(1) 3.598 ? . 3_646 H(11) H(5) 3.538 ? . 3_646 H(11) H(6) 2.902 ? . 3_646 H(11) H(8) 3.386 ? . 3_746 H(11) H(18) 3.537 ? . 2_557 H(12) C(5) 3.457 ? . 4_665 H(12) C(14) 3.132 ? . 2_557 H(12) H(5) 2.492 ? . 4_665 H(12) H(10) 3.360 ? . 2_457 H(12) H(17) 3.263 ? . 2_557 H(12) H(18) 3.086 ? . 2_557 H(12) H(19) 2.566 ? . 2_557 H(13) O(2) 3.002 ? . 2_567 H(13) O(3) 3.226 ? . 4_665 H(13) C(5) 3.595 ? . 4_665 H(13) C(14) 3.346 ? . 1_655 H(13) H(4) 3.520 ? . 4_665 H(13) H(5) 2.792 ? . 4_665 H(13) H(17) 2.462 ? . 1_655 H(13) H(18) 3.577 ? . 2_557 H(13) H(19) 3.538 ? . 1_655 H(13) H(19) 3.126 ? . 2_557 H(13) H(3A) 2.846 ? . 4_665 H(14) O(2) 2.964 ? . 2_567 H(14) O(4) 2.578 ? . 2_467 H(14) C(1) 3.516 ? . 2_567 H(14) H(4) 2.910 ? . 4_665 H(14) H(5) 3.159 ? . 4_665 H(14) H(16) 3.286 ? . 2_567 H(14) H(3A) 3.366 ? . 4_665 H(15) O(2) 3.000 ? . 2_567 H(15) C(13) 3.208 ? . 2_567 H(15) H(16) 2.256 ? . 2_567 H(15) H(17) 3.509 ? . 2_567 H(16) O(2) 3.288 ? . 2_467 H(16) O(4) 3.456 ? . 2_467 H(16) C(12) 3.161 ? . 2_467 H(16) H(9) 3.342 ? . 2_467 H(16) H(14) 3.286 ? . 2_467 H(16) H(15) 2.256 ? . 2_467 H(17) O(2) 2.890 ? . 2_467 H(17) O(3) 3.294 ? . 4_565 H(17) C(9) 3.470 ? . 1_455 H(17) C(11) 3.337 ? . 1_455 H(17) H(9) 2.720 ? . 1_455 H(17) H(10) 3.496 ? . 1_455 H(17) H(12) 3.263 ? . 2_457 H(17) H(13) 2.462 ? . 1_455 H(17) H(15) 3.509 ? . 2_467 H(17) H(3A) 2.840 ? . 4_565 H(18) O(3) 3.314 ? . 4_565 H(18) C(10) 3.285 ? . 2_457 H(18) C(11) 3.527 ? . 2_457 H(18) H(5) 3.432 ? . 4_665 H(18) H(7) 3.248 ? . 4_665 H(18) H(10) 2.501 ? . 2_457 H(18) H(11) 3.537 ? . 2_457 H(18) H(12) 3.086 ? . 2_457 H(18) H(13) 3.577 ? . 2_457 H(18) H(3A) 3.178 ? . 4_565 H(19) C(5) 3.299 ? . 3_646 H(19) C(11) 3.221 ? . 2_457 H(19) H(5) 2.581 ? . 3_646 H(19) H(6) 3.129 ? . 3_646 H(19) H(9) 3.304 ? . 1_455 H(19) H(10) 3.192 ? . 2_457 H(19) H(12) 2.566 ? . 2_457 H(19) H(13) 3.538 ? . 1_455 H(19) H(13) 3.126 ? . 2_457 H(3A) O(2) 1.93(3) ? . 3_646 H(3A) C(1) 2.75(3) ? . 3_646 H(3A) C(2) 3.08(3) ? . 3_646 H(3A) C(14) 3.45(3) ? . 4_564 H(3A) H(1) 2.507 ? . 3_646 H(3A) H(13) 2.846 ? . 4_664 H(3A) H(14) 3.366 ? . 4_664 H(3A) H(17) 2.840 ? . 4_564 H(3A) H(18) 3.178 ? . 4_564 #============================================================================== # 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 #============================================================================== # Attachment '- (g)-Compound 24.cif' #============================================================================== data__User-defined _database_code_depnum_ccdc_archive 'CCDC 820819' #TrackingRef '- (g)-Compound 24.cif' _audit_creation_date 2009-02-23 _audit_creation_method 'by CrystalStructure 3.8' _audit_update_record ? #============================================================================== # CHEMICAL DATA _chemical_formula_sum 'C13 H18 O3 ' _chemical_formula_moiety 'C13 H18 O3 ' _chemical_formula_weight 222.28 _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 12.956(2) _cell_length_b 8.4492(15) _cell_length_c 11.2977(20) _cell_angle_alpha 90.0000 _cell_angle_beta 90.405(4) _cell_angle_gamma 90.0000 _cell_volume 1236.7(4) _cell_formula_units_Z 4 _cell_measurement_reflns_used 6056 _cell_measurement_theta_min 3.0 _cell_measurement_theta_max 27.5 _cell_measurement_temperature 223.1 #------------------------------------------------------------------------------ _exptl_crystal_description Platelet _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_diffrn 1.194 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 480.00 _exptl_absorpt_coefficient_mu 0.083 _exptl_absorpt_correction_type none #============================================================================== # EXPERIMENTAL DATA _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71075 _diffrn_measurement_device_type 'Rigaku SCXmini' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 6.85 _diffrn_reflns_number 7859 _diffrn_reflns_av_R_equivalents 0.050 _diffrn_reflns_theta_max 27.48 _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.992 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 11 #============================================================================== # 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 2812 _reflns_number_gt 1673 _reflns_threshold_expression F^2^>2.0\s(F^2^) _refine_ls_structure_factor_coef Fsqd _refine_ls_R_factor_gt 0.0665 _refine_ls_wR_factor_ref 0.1613 _refine_ls_hydrogen_treatment refall _refine_ls_number_reflns 2812 _refine_ls_number_parameters 146 _refine_ls_goodness_of_fit_ref 1.066 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.0478P)^2^+0.4198P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_shift/su_max 0.0000 _refine_diff_density_max 0.15 _refine_diff_density_min -0.13 _refine_ls_extinction_method none _refine_ls_extinction_coef ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source O O 0.011 0.006 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; C C 0.003 0.002 ; 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) ; #============================================================================== # 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 0.65639(13) 0.6625(2) 0.30315(14) 0.0627(4) Uani 1.00 1 d . . . O(2) O 0.62587(17) 0.7118(2) 0.11068(17) 0.0859(6) Uani 1.00 1 d . . . O(3) O 0.82337(18) 0.3443(2) -0.05998(17) 0.0894(6) Uani 1.00 1 d . . . C(1) C 0.62518(18) 0.6221(3) 0.1937(2) 0.0581(6) Uani 1.00 1 d . . . C(2) C 0.59663(17) 0.4550(3) 0.1894(2) 0.0579(6) Uani 1.00 1 d . . . C(3) C 0.58952(17) 0.3740(3) 0.0904(2) 0.0605(6) Uani 1.00 1 d . . . C(4) C 0.58014(19) 0.1985(3) 0.0822(2) 0.0681(7) Uani 1.00 1 d . . . C(5) C 0.67781(19) 0.1236(3) 0.0327(2) 0.0625(6) Uani 1.00 1 d . . . C(6) C 0.77589(17) 0.1760(2) 0.0973(2) 0.0532(5) Uani 1.00 1 d . . . C(7) C 0.82623(18) 0.3213(2) 0.0459(2) 0.0547(5) Uani 1.00 1 d . . . C(8) C 0.88439(17) 0.4335(2) 0.1212(2) 0.0581(6) Uani 1.00 1 d . . . C(9) C 0.88545(17) 0.4402(2) 0.2361(2) 0.0576(6) Uani 1.00 1 d . . . C(10) C 0.94528(19) 0.5585(3) 0.3093(2) 0.0690(7) Uani 1.00 1 d . . . C(11) C 0.8749(2) 0.6743(3) 0.3735(2) 0.0673(7) Uani 1.00 1 d . . . C(12) C 0.8208(2) 0.7933(3) 0.2927(2) 0.0657(7) Uani 1.00 1 d . . . C(13) C 0.7085(2) 0.8135(3) 0.3181(2) 0.0679(7) Uani 1.00 1 d . . . H(1) H 0.5827 0.4028 0.2610 0.070 Uiso 1.00 1 c R . . H(2) H 0.5904 0.4313 0.0191 0.073 Uiso 1.00 1 c R . . H(3) H 0.5214 0.1715 0.0309 0.082 Uiso 1.00 1 c R . . H(4) H 0.5667 0.1551 0.1610 0.082 Uiso 1.00 1 c R . . H(5) H 0.6836 0.1513 -0.0512 0.075 Uiso 1.00 1 c R . . H(6) H 0.6719 0.0082 0.0382 0.075 Uiso 1.00 1 c R . . H(7) H 0.7591 0.1971 0.1803 0.064 Uiso 1.00 1 c R . . H(8) H 0.8257 0.0887 0.0960 0.064 Uiso 1.00 1 c R . . H(9) H 0.9252 0.5084 0.0816 0.070 Uiso 1.00 1 c R . . H(10) H 0.8457 0.3652 0.2769 0.069 Uiso 1.00 1 c R . . H(11) H 0.9918 0.6178 0.2576 0.083 Uiso 1.00 1 c R . . H(12) H 0.9877 0.5018 0.3676 0.083 Uiso 1.00 1 c R . . H(13) H 0.9161 0.7325 0.4322 0.081 Uiso 1.00 1 c R . . H(14) H 0.8225 0.6140 0.4163 0.081 Uiso 1.00 1 c R . . H(15) H 0.8550 0.8962 0.3009 0.079 Uiso 1.00 1 c R . . H(16) H 0.8285 0.7588 0.2105 0.079 Uiso 1.00 1 c R . . H(17) H 0.6996 0.8516 0.3993 0.081 Uiso 1.00 1 c R . . H(18) H 0.6786 0.8919 0.2639 0.081 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) 0.0624(10) 0.0710(11) 0.0549(10) -0.0030(8) 0.0049(7) 0.0013(8) O(2) 0.1217(17) 0.0684(12) 0.0673(12) 0.0119(11) -0.0139(10) 0.0111(9) O(3) 0.1263(18) 0.0834(14) 0.0586(12) -0.0173(12) 0.0140(10) -0.0013(9) C(1) 0.0550(14) 0.0646(16) 0.0548(15) 0.0144(11) 0.0019(11) 0.0032(12) C(2) 0.0463(13) 0.0697(16) 0.0578(15) 0.0031(11) -0.0019(10) 0.0065(12) C(3) 0.0443(13) 0.0732(17) 0.0640(16) 0.0090(11) -0.0093(10) 0.0040(13) C(4) 0.0520(14) 0.0741(18) 0.0780(18) -0.0066(12) -0.0111(11) -0.0051(13) C(5) 0.0614(15) 0.0568(14) 0.0693(16) -0.0036(11) -0.0084(11) -0.0083(12) C(6) 0.0517(13) 0.0471(13) 0.0608(14) 0.0055(10) -0.0049(10) -0.0006(10) C(7) 0.0571(14) 0.0515(13) 0.0555(15) 0.0047(10) 0.0059(10) -0.0039(11) C(8) 0.0524(14) 0.0519(14) 0.0700(17) -0.0029(10) 0.0123(11) -0.0010(11) C(9) 0.0453(13) 0.0532(14) 0.0743(18) -0.0017(10) -0.0002(10) -0.0004(11) C(10) 0.0521(14) 0.0682(17) 0.0866(19) -0.0083(12) -0.0114(12) -0.0122(13) C(11) 0.0676(16) 0.0667(17) 0.0677(17) -0.0127(13) -0.0027(12) -0.0097(13) C(12) 0.0748(17) 0.0515(14) 0.0711(17) -0.0092(12) 0.0146(12) -0.0062(12) C(13) 0.0832(18) 0.0549(15) 0.0658(17) 0.0028(13) 0.0092(13) -0.0103(12) #============================================================================== _computing_data_collection PROCESS-AUTO _computing_cell_refinement PROCESS-AUTO _computing_data_reduction CrystalStructure _computing_structure_solution SHELXS97 _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(1) 1.343(2) yes . . O(1) C(13) 1.453(3) yes . . O(2) C(1) 1.206(3) yes . . O(3) C(7) 1.212(3) yes . . C(1) C(2) 1.460(3) yes . . C(2) C(3) 1.314(3) yes . . C(3) C(4) 1.491(3) yes . . C(4) C(5) 1.524(3) yes . . C(5) C(6) 1.527(3) yes . . C(6) C(7) 1.508(3) yes . . C(7) C(8) 1.477(3) yes . . C(8) C(9) 1.299(3) yes . . C(9) C(10) 1.508(3) yes . . C(10) C(11) 1.524(3) yes . . C(11) C(12) 1.526(3) yes . . C(12) C(13) 1.494(3) yes . . C(2) H(1) 0.940 no . . C(3) H(2) 0.940 no . . C(4) H(3) 0.980 no . . C(4) H(4) 0.980 no . . C(5) H(5) 0.980 no . . C(5) H(6) 0.980 no . . C(6) H(7) 0.980 no . . C(6) H(8) 0.980 no . . C(8) H(9) 0.940 no . . C(9) H(10) 0.940 no . . C(10) H(11) 0.980 no . . C(10) H(12) 0.980 no . . C(11) H(13) 0.980 no . . C(11) H(14) 0.980 no . . C(12) H(15) 0.980 no . . C(12) H(16) 0.980 no . . C(13) H(17) 0.980 no . . C(13) H(18) 0.980 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(1) O(1) C(13) 117.84(19) yes . . . O(1) C(1) O(2) 123.6(2) yes . . . O(1) C(1) C(2) 110.5(2) yes . . . O(2) C(1) C(2) 125.8(2) yes . . . C(1) C(2) C(3) 123.2(2) yes . . . C(2) C(3) C(4) 125.2(2) yes . . . C(3) C(4) C(5) 111.6(2) yes . . . C(4) C(5) C(6) 113.2(2) yes . . . C(5) C(6) C(7) 114.40(19) yes . . . O(3) C(7) C(6) 120.0(2) yes . . . O(3) C(7) C(8) 118.5(2) yes . . . C(6) C(7) C(8) 121.4(2) yes . . . C(7) C(8) C(9) 127.3(2) yes . . . C(8) C(9) C(10) 125.3(2) yes . . . C(9) C(10) C(11) 112.3(2) yes . . . C(10) C(11) C(12) 114.3(2) yes . . . C(11) C(12) C(13) 113.9(2) yes . . . O(1) C(13) C(12) 109.3(2) yes . . . C(1) C(2) H(1) 118.4 no . . . C(3) C(2) H(1) 118.4 no . . . C(2) C(3) H(2) 117.4 no . . . C(4) C(3) H(2) 117.4 no . . . C(3) C(4) H(3) 109.3 no . . . C(3) C(4) H(4) 109.3 no . . . C(5) C(4) H(3) 109.3 no . . . C(5) C(4) H(4) 109.3 no . . . H(3) C(4) H(4) 108.0 no . . . C(4) C(5) H(5) 108.9 no . . . C(4) C(5) H(6) 108.9 no . . . C(6) C(5) H(5) 108.9 no . . . C(6) C(5) H(6) 108.9 no . . . H(5) C(5) H(6) 107.7 no . . . C(5) C(6) H(7) 108.7 no . . . C(5) C(6) H(8) 108.7 no . . . C(7) C(6) H(7) 108.7 no . . . C(7) C(6) H(8) 108.7 no . . . H(7) C(6) H(8) 107.6 no . . . C(7) C(8) H(9) 116.4 no . . . C(9) C(8) H(9) 116.4 no . . . C(8) C(9) H(10) 117.3 no . . . C(10) C(9) H(10) 117.3 no . . . C(9) C(10) H(11) 109.1 no . . . C(9) C(10) H(12) 109.1 no . . . C(11) C(10) H(11) 109.1 no . . . C(11) C(10) H(12) 109.1 no . . . H(11) C(10) H(12) 107.9 no . . . C(10) C(11) H(13) 108.7 no . . . C(10) C(11) H(14) 108.7 no . . . C(12) C(11) H(13) 108.7 no . . . C(12) C(11) H(14) 108.7 no . . . H(13) C(11) H(14) 107.6 no . . . C(11) C(12) H(15) 108.8 no . . . C(11) C(12) H(16) 108.8 no . . . C(13) C(12) H(15) 108.8 no . . . C(13) C(12) H(16) 108.8 no . . . H(15) C(12) H(16) 107.7 no . . . O(1) C(13) H(17) 109.8 no . . . O(1) C(13) H(18) 109.8 no . . . C(12) C(13) H(17) 109.8 no . . . C(12) C(13) H(18) 109.8 no . . . H(17) C(13) H(18) 108.3 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(1) O(1) C(13) C(12) -85.0(2) ? . . . . C(13) O(1) C(1) O(2) -10.0(3) ? . . . . C(13) O(1) C(1) C(2) 166.91(19) ? . . . . O(1) C(1) C(2) C(3) -161.6(2) ? . . . . O(2) C(1) C(2) C(3) 15.2(3) ? . . . . C(1) C(2) C(3) C(4) 168.0(2) ? . . . . C(2) C(3) C(4) C(5) -110.2(2) ? . . . . C(3) C(4) C(5) C(6) 51.6(2) ? . . . . C(4) C(5) C(6) C(7) -90.2(2) ? . . . . C(5) C(6) C(7) O(3) -34.3(3) ? . . . . C(5) C(6) C(7) C(8) 149.0(2) ? . . . . O(3) C(7) C(8) C(9) 170.6(2) ? . . . . C(6) C(7) C(8) C(9) -12.7(3) ? . . . . C(7) C(8) C(9) C(10) -179.2(2) ? . . . . C(8) C(9) C(10) C(11) 111.9(2) ? . . . . C(9) C(10) C(11) C(12) -70.6(2) ? . . . . C(10) C(11) C(12) C(13) 134.5(2) ? . . . . C(11) C(12) C(13) O(1) -60.0(2) ? . . . . 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(4) 3.349(3) ? . 2_655 O(1) C(5) 3.555(3) ? . 4_555 O(2) C(4) 3.516(3) ? . 3_665 O(2) C(13) 3.488(3) ? . 4_564 O(3) C(9) 3.429(3) ? . 4_554 O(3) C(12) 3.485(3) ? . 4_564 O(3) C(13) 3.528(3) ? . 4_564 C(4) O(1) 3.349(3) ? . 2_645 C(4) O(2) 3.516(3) ? . 3_665 C(5) O(1) 3.555(3) ? . 4_554 C(9) O(3) 3.429(3) ? . 4_555 C(12) O(3) 3.485(3) ? . 4_565 C(13) O(2) 3.488(3) ? . 4_565 C(13) O(3) 3.528(3) ? . 4_565 O(1) H(3) 2.981 ? . 2_655 O(1) H(4) 2.923 ? . 2_655 O(1) H(5) 3.139 ? . 4_555 O(1) H(6) 3.027 ? . 4_555 O(2) H(1) 3.473 ? . 2_655 O(2) H(2) 3.377 ? . 3_665 O(2) H(3) 2.670 ? . 3_665 O(2) H(6) 2.703 ? . 1_565 O(2) H(17) 2.633 ? . 4_564 O(3) H(7) 3.065 ? . 4_554 O(3) H(9) 3.498 ? . 3_765 O(3) H(10) 2.572 ? . 4_554 O(3) H(11) 3.301 ? . 3_765 O(3) H(15) 2.731 ? . 4_564 O(3) H(17) 3.062 ? . 4_564 O(3) H(18) 3.521 ? . 4_564 C(1) H(4) 3.002 ? . 2_655 C(1) H(17) 3.476 ? . 4_564 C(2) H(2) 3.501 ? . 3_665 C(2) H(4) 3.201 ? . 2_655 C(2) H(5) 3.259 ? . 4_555 C(3) H(2) 3.103 ? . 3_665 C(3) H(17) 3.480 ? . 4_564 C(4) H(18) 3.538 ? . 1_545 C(5) H(1) 3.308 ? . 4_554 C(5) H(14) 3.051 ? . 4_554 C(5) H(18) 3.264 ? . 1_545 C(6) H(11) 3.453 ? . 2_745 C(6) H(12) 3.419 ? . 2_745 C(6) H(14) 3.251 ? . 4_554 C(6) H(15) 3.450 ? . 1_545 C(6) H(18) 3.306 ? . 1_545 C(7) H(10) 3.434 ? . 4_554 C(7) H(13) 3.429 ? . 2_745 C(8) H(9) 3.415 ? . 3_765 C(8) H(11) 3.396 ? . 2_745 C(8) H(13) 3.155 ? . 2_745 C(8) H(13) 3.565 ? . 4_564 C(8) H(15) 3.497 ? . 2_745 C(9) H(11) 3.155 ? . 2_745 C(9) H(15) 3.411 ? . 2_745 C(10) H(8) 3.158 ? . 2_755 C(10) H(15) 3.189 ? . 2_745 C(11) H(6) 3.582 ? . 4_555 C(11) H(8) 3.419 ? . 4_555 C(12) H(8) 3.343 ? . 1_565 C(12) H(12) 3.550 ? . 2_755 C(13) H(2) 3.492 ? . 4_565 C(13) H(6) 3.593 ? . 1_565 H(1) O(2) 3.473 ? . 2_645 H(1) C(5) 3.308 ? . 4_555 H(1) H(3) 3.541 ? . 2_655 H(1) H(3) 3.219 ? . 4_555 H(1) H(4) 3.015 ? . 2_655 H(1) H(5) 2.526 ? . 4_555 H(1) H(6) 3.415 ? . 4_555 H(1) H(18) 3.395 ? . 2_645 H(2) O(2) 3.377 ? . 3_665 H(2) C(2) 3.501 ? . 3_665 H(2) C(3) 3.103 ? . 3_665 H(2) C(13) 3.492 ? . 4_564 H(2) H(2) 2.647 ? . 3_665 H(2) H(17) 2.687 ? . 4_564 H(2) H(18) 3.448 ? . 4_564 H(3) O(1) 2.981 ? . 2_645 H(3) O(2) 2.670 ? . 3_665 H(3) H(1) 3.541 ? . 2_645 H(3) H(1) 3.219 ? . 4_554 H(3) H(3) 3.032 ? . 3_655 H(3) H(6) 3.026 ? . 3_655 H(3) H(17) 3.341 ? . 2_645 H(4) O(1) 2.923 ? . 2_645 H(4) C(1) 3.002 ? . 2_645 H(4) C(2) 3.201 ? . 2_645 H(4) H(1) 3.015 ? . 2_645 H(4) H(18) 2.893 ? . 1_545 H(5) O(1) 3.139 ? . 4_554 H(5) C(2) 3.259 ? . 4_554 H(5) H(1) 2.526 ? . 4_554 H(5) H(7) 3.442 ? . 4_554 H(5) H(10) 2.874 ? . 4_554 H(5) H(14) 2.899 ? . 4_554 H(6) O(1) 3.027 ? . 4_554 H(6) O(2) 2.703 ? . 1_545 H(6) C(11) 3.582 ? . 4_554 H(6) C(13) 3.593 ? . 1_545 H(6) H(1) 3.415 ? . 4_554 H(6) H(3) 3.026 ? . 3_655 H(6) H(14) 2.609 ? . 4_554 H(6) H(16) 3.505 ? . 1_545 H(6) H(17) 3.441 ? . 4_554 H(6) H(18) 2.734 ? . 1_545 H(7) O(3) 3.065 ? . 4_555 H(7) H(5) 3.442 ? . 4_555 H(7) H(11) 3.366 ? . 2_745 H(7) H(15) 3.138 ? . 1_545 H(7) H(18) 2.941 ? . 1_545 H(8) C(10) 3.158 ? . 2_745 H(8) C(11) 3.419 ? . 4_554 H(8) C(12) 3.343 ? . 1_545 H(8) H(11) 2.887 ? . 2_745 H(8) H(12) 2.558 ? . 2_745 H(8) H(12) 3.424 ? . 4_554 H(8) H(13) 3.576 ? . 2_745 H(8) H(13) 3.491 ? . 4_554 H(8) H(14) 2.656 ? . 4_554 H(8) H(15) 2.853 ? . 1_545 H(8) H(16) 3.073 ? . 1_545 H(8) H(18) 3.171 ? . 1_545 H(9) O(3) 3.498 ? . 3_765 H(9) C(8) 3.415 ? . 3_765 H(9) H(9) 2.689 ? . 3_765 H(9) H(13) 3.114 ? . 2_745 H(9) H(13) 2.766 ? . 4_564 H(9) H(15) 3.273 ? . 2_745 H(9) H(15) 3.391 ? . 4_564 H(10) O(3) 2.573 ? . 4_555 H(10) C(7) 3.434 ? . 4_555 H(10) H(5) 2.874 ? . 4_555 H(10) H(11) 2.995 ? . 2_745 H(11) O(3) 3.301 ? . 3_765 H(11) C(6) 3.453 ? . 2_755 H(11) C(8) 3.396 ? . 2_755 H(11) C(9) 3.155 ? . 2_755 H(11) H(7) 3.366 ? . 2_755 H(11) H(8) 2.887 ? . 2_755 H(11) H(10) 2.995 ? . 2_755 H(11) H(12) 3.550 ? . 2_755 H(11) H(15) 2.810 ? . 2_745 H(12) C(6) 3.419 ? . 2_755 H(12) C(12) 3.550 ? . 2_745 H(12) H(8) 2.558 ? . 2_755 H(12) H(8) 3.424 ? . 4_555 H(12) H(11) 3.550 ? . 2_745 H(12) H(12) 3.007 ? . 3_766 H(12) H(13) 3.248 ? . 3_766 H(12) H(14) 3.589 ? . 3_766 H(12) H(15) 2.937 ? . 2_745 H(12) H(16) 3.270 ? . 2_745 H(13) C(7) 3.429 ? . 2_755 H(13) C(8) 3.155 ? . 2_755 H(13) C(8) 3.565 ? . 4_565 H(13) H(8) 3.576 ? . 2_755 H(13) H(8) 3.491 ? . 4_555 H(13) H(9) 3.114 ? . 2_755 H(13) H(9) 2.766 ? . 4_565 H(13) H(12) 3.248 ? . 3_766 H(13) H(16) 3.350 ? . 4_565 H(14) C(5) 3.051 ? . 4_555 H(14) C(6) 3.251 ? . 4_555 H(14) H(5) 2.899 ? . 4_555 H(14) H(6) 2.609 ? . 4_555 H(14) H(8) 2.656 ? . 4_555 H(14) H(12) 3.589 ? . 3_766 H(14) H(16) 3.493 ? . 4_565 H(15) O(3) 2.731 ? . 4_565 H(15) C(6) 3.450 ? . 1_565 H(15) C(8) 3.497 ? . 2_755 H(15) C(9) 3.411 ? . 2_755 H(15) C(10) 3.189 ? . 2_755 H(15) H(7) 3.138 ? . 1_565 H(15) H(8) 2.853 ? . 1_565 H(15) H(9) 3.273 ? . 2_755 H(15) H(9) 3.391 ? . 4_565 H(15) H(11) 2.810 ? . 2_755 H(15) H(12) 2.937 ? . 2_755 H(16) H(6) 3.505 ? . 1_565 H(16) H(8) 3.073 ? . 1_565 H(16) H(12) 3.270 ? . 2_755 H(16) H(13) 3.350 ? . 4_564 H(16) H(14) 3.493 ? . 4_564 H(17) O(2) 2.633 ? . 4_565 H(17) O(3) 3.062 ? . 4_565 H(17) C(1) 3.476 ? . 4_565 H(17) C(3) 3.480 ? . 4_565 H(17) H(2) 2.687 ? . 4_565 H(17) H(3) 3.341 ? . 2_655 H(17) H(6) 3.441 ? . 4_555 H(18) O(3) 3.521 ? . 4_565 H(18) C(4) 3.538 ? . 1_565 H(18) C(5) 3.264 ? . 1_565 H(18) C(6) 3.306 ? . 1_565 H(18) H(1) 3.395 ? . 2_655 H(18) H(2) 3.448 ? . 4_565 H(18) H(4) 2.893 ? . 1_565 H(18) H(6) 2.734 ? . 1_565 H(18) H(7) 2.941 ? . 1_565 H(18) H(8) 3.171 ? . 1_565 #============================================================================== # 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 #============================================================================== # Attachment '- (h)-Compound 26.cif' #============================================================================== data__ad05 _database_code_depnum_ccdc_archive 'CCDC 820820' #TrackingRef '- (h)-Compound 26.cif' _audit_creation_date 2010-09-01 _audit_creation_method 'by CrystalStructure 4.0' _audit_update_record ? #============================================================================== # CHEMICAL DATA _chemical_formula_sum 'C14 H22 O4' _chemical_formula_moiety 'C14 H22 O4' _chemical_formula_weight 254.33 _chemical_melting_point ? _chemical_absolute_configuration ad #============================================================================== # CRYSTAL DATA _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' _symmetry_space_group_name_Hall 'P 2ac 2ab' _symmetry_Int_Tables_number 19 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 +X,+Y,+Z 2 1/2+X,1/2-Y,-Z 3 -X,1/2+Y,1/2-Z 4 1/2-X,-Y,1/2+Z #------------------------------------------------------------------------------ _cell_length_a 6.16325(11) _cell_length_b 11.2731(2) _cell_length_c 18.7642(13) _cell_angle_alpha 90.0000 _cell_angle_beta 90.0000 _cell_angle_gamma 90.0000 _cell_volume 1303.72(10) _cell_formula_units_Z 4 _cell_measurement_reflns_used 5583 _cell_measurement_theta_min 7.57 _cell_measurement_theta_max 65.88 _cell_measurement_temperature 93 #------------------------------------------------------------------------------ _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.08 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.07 _exptl_crystal_density_diffrn 1.296 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 552.00 _exptl_absorpt_coefficient_mu 0.766 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _exptl_absorpt_correction_T_min 0.697 _exptl_absorpt_correction_T_max 0.948 #============================================================================== # EXPERIMENTAL DATA _diffrn_ambient_temperature 93 _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54187 _diffrn_measurement_device_type 'Rigaku Saturn724 CCD' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 11.111 _diffrn_reflns_number 5898 _diffrn_reflns_av_R_equivalents 0.0376 _diffrn_reflns_theta_max 65.88 _diffrn_reflns_theta_full 65.88 _diffrn_measured_fraction_theta_max 0.967 _diffrn_measured_fraction_theta_full 0.967 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 21 _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_decay_% ? #============================================================================== # 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 2194 _reflns_number_gt 2102 _reflns_threshold_expression F^2^>2.0\s(F^2^) _refine_ls_structure_factor_coef Fsqd _refine_ls_R_factor_gt 0.0336 _refine_ls_wR_factor_ref 0.0832 _refine_ls_number_restraints 0 _refine_ls_hydrogen_treatment mixed _refine_ls_number_reflns 2194 _refine_ls_number_parameters 167 _refine_ls_goodness_of_fit_ref 1.055 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.0388P)^2^+0.2996P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _refine_ls_shift/su_max 0.001 _refine_diff_density_max 0.140 _refine_diff_density_min -0.170 _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack, H. D. (1983), Acta Cryst. A39, 876-881. 872 Friedel Pairs' _refine_ls_abs_structure_Flack 0.22(20) 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 1.0271(2) 0.13254(11) 1.04621(6) 0.0256(3) Uani 1.00 4 d . . . O(2) O 0.5816(2) -0.13137(10) 0.92788(6) 0.0283(3) Uani 1.00 4 d . . . O(3) O 0.99509(19) 0.22063(10) 0.78303(5) 0.0221(3) Uani 1.00 4 d . . . O(4) O 0.8218(2) 0.37404(11) 0.83481(6) 0.0276(3) Uani 1.00 4 d . . . C(1) C 1.1147(3) 0.06541(15) 0.98772(8) 0.0231(4) Uani 1.00 4 d . . . C(2) C 1.1000(3) -0.06708(15) 1.00199(9) 0.0261(4) Uani 1.00 4 d . . . C(3) C 0.8654(3) -0.10543(16) 1.01197(9) 0.0270(4) Uani 1.00 4 d . . . C(4) C 0.7214(3) -0.06653(15) 0.95177(8) 0.0222(4) Uani 1.00 4 d . . . C(5) C 0.7479(3) 0.06075(14) 0.92483(8) 0.0211(3) Uani 1.00 4 d . . . C(6) C 0.6153(3) 0.08082(15) 0.85680(8) 0.0217(4) Uani 1.00 4 d . . . C(7) C 0.7007(3) 0.01775(14) 0.78973(8) 0.0224(4) Uani 1.00 4 d . . . C(8) C 0.6189(3) 0.07247(16) 0.71994(9) 0.0256(4) Uani 1.00 4 d . . . C(9) C 0.6620(3) 0.20567(15) 0.71025(9) 0.0243(4) Uani 1.00 4 d . . . C(10) C 0.8962(3) 0.24754(14) 0.71310(9) 0.0229(4) Uani 1.00 4 d . . . C(11) C 1.0442(3) 0.18842(16) 0.65941(9) 0.0265(4) Uani 1.00 4 d . . . C(12) C 0.9319(3) 0.28469(15) 0.83907(8) 0.0225(4) Uani 1.00 4 d . . . C(13) C 1.0164(3) 0.23445(14) 0.90822(8) 0.0223(3) Uani 1.00 4 d . . . C(14) C 0.9891(3) 0.09992(13) 0.92040(8) 0.0207(3) Uani 1.00 4 d . . . H(1) H 1.2706 0.0875 0.9812 0.028 Uiso 1.00 4 calc R . . H(2A) H 1.1841 -0.0867 1.0454 0.031 Uiso 1.00 4 calc R . . H(2B) H 1.1644 -0.1111 0.9615 0.031 Uiso 1.00 4 calc R . . H(3A) H 0.8597 -0.1930 1.0159 0.032 Uiso 1.00 4 calc R . . H(3B) H 0.8097 -0.0717 1.0571 0.032 Uiso 1.00 4 calc R . . H(5) H 0.6801 0.1124 0.9620 0.025 Uiso 1.00 4 calc R . . H(6A) H 0.6100 0.1671 0.8471 0.026 Uiso 1.00 4 calc R . . H(6B) H 0.4648 0.0539 0.8656 0.026 Uiso 1.00 4 calc R . . H(7A) H 0.8612 0.0203 0.7901 0.027 Uiso 1.00 4 calc R . . H(7B) H 0.6562 -0.0666 0.7914 0.027 Uiso 1.00 4 calc R . . H(8A) H 0.4604 0.0590 0.7168 0.031 Uiso 1.00 4 calc R . . H(8B) H 0.6872 0.0296 0.6798 0.031 Uiso 1.00 4 calc R . . H(9A) H 0.6009 0.2298 0.6636 0.029 Uiso 1.00 4 calc R . . H(9B) H 0.5801 0.2487 0.7475 0.029 Uiso 1.00 4 calc R . . H(10) H 0.8999 0.3353 0.7053 0.028 Uiso 1.00 4 calc R . . H(11A) H 1.0513 0.1031 0.6693 0.032 Uiso 1.00 4 calc R . . H(11B) H 1.1899 0.2227 0.6630 0.032 Uiso 1.00 4 calc R . . H(11C) H 0.9872 0.2011 0.6112 0.032 Uiso 1.00 4 calc R . . H(13A) H 0.9430 0.2764 0.9478 0.027 Uiso 1.00 4 calc R . . H(13B) H 1.1729 0.2533 0.9115 0.027 Uiso 1.00 4 calc R . . H(14) H 1.0569 0.0578 0.8791 0.025 Uiso 1.00 4 calc R . . H(1A) H 1.104(4) 0.116(2) 1.0833(14) 0.058(8) Uiso 1.00 4 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_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 O(1) 0.0291(7) 0.0287(6) 0.0190(6) 0.0026(6) -0.0016(5) -0.0040(5) O(2) 0.0306(7) 0.0271(6) 0.0271(6) -0.0066(5) -0.0008(5) 0.0008(5) O(3) 0.0258(6) 0.0218(5) 0.0188(5) 0.0007(5) -0.0008(5) -0.0003(4) O(4) 0.0371(7) 0.0213(6) 0.0245(6) 0.0036(6) 0.0033(5) 0.0001(5) C(1) 0.0231(8) 0.0270(9) 0.0192(8) 0.0008(7) 0.0004(7) -0.0026(7) C(2) 0.0290(9) 0.0258(9) 0.0234(8) 0.0045(8) -0.0047(8) 0.0012(7) C(3) 0.0352(10) 0.0229(9) 0.0228(8) -0.0006(8) -0.0009(8) 0.0034(7) C(4) 0.0235(9) 0.0235(9) 0.0195(8) -0.0008(8) 0.0030(7) -0.0022(6) C(5) 0.0215(8) 0.0210(8) 0.0209(8) 0.0003(7) 0.0009(7) -0.0003(7) C(6) 0.0207(8) 0.0225(8) 0.0219(8) -0.0013(7) -0.0002(7) 0.0014(7) C(7) 0.0221(8) 0.0225(8) 0.0224(8) -0.0017(7) -0.0006(7) 0.0003(7) C(8) 0.0264(9) 0.0285(9) 0.0220(8) -0.0037(8) -0.0013(7) 0.0006(7) C(9) 0.0252(9) 0.0283(9) 0.0194(8) 0.0031(7) -0.0014(7) 0.0033(7) C(10) 0.0286(9) 0.0211(9) 0.0191(8) 0.0019(7) -0.0017(7) 0.0035(6) C(11) 0.0303(10) 0.0279(9) 0.0215(8) -0.0018(7) 0.0004(7) -0.0004(7) C(12) 0.0238(9) 0.0198(8) 0.0237(8) -0.0029(7) 0.0029(7) -0.0010(7) C(13) 0.0235(9) 0.0222(8) 0.0214(8) -0.0021(7) 0.0001(7) -0.0020(6) C(14) 0.0220(8) 0.0211(8) 0.0190(7) 0.0005(7) 0.0008(7) -0.0015(6) #============================================================================== _computing_data_collection 'CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)' _computing_cell_refinement 'CrystalClear-SM Expert 2.0 r4' _computing_data_reduction 'CrystalClear-SM Expert 2.0 r4' _computing_structure_solution 'SIR2004 (Burla, et al., 2005)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_publication_material 'CrystalStructure 4.0 (Rigaku, 2010)' _computing_molecular_graphics 'CrystalStructure 4.0' #============================================================================== # 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(1) 1.4384(20) yes . . O(2) C(4) 1.215(2) yes . . O(3) C(10) 1.4784(20) yes . . O(3) C(12) 1.3338(19) yes . . O(4) C(12) 1.217(2) yes . . C(1) C(2) 1.520(2) yes . . C(1) C(14) 1.532(2) yes . . C(2) C(3) 1.521(3) yes . . C(3) C(4) 1.502(2) yes . . C(4) C(5) 1.530(2) yes . . C(5) C(6) 1.532(2) yes . . C(5) C(14) 1.553(2) yes . . C(6) C(7) 1.538(2) yes . . C(7) C(8) 1.533(2) yes . . C(8) C(9) 1.536(2) yes . . C(9) C(10) 1.519(2) yes . . C(10) C(11) 1.514(2) yes . . C(12) C(13) 1.508(2) yes . . C(13) C(14) 1.543(2) yes . . O(1) H(1A) 0.86(3) yes . . C(1) H(1) 1.000 yes . . C(2) H(2A) 0.990 yes . . C(2) H(2B) 0.990 yes . . C(3) H(3A) 0.990 yes . . C(3) H(3B) 0.990 yes . . C(5) H(5) 1.000 yes . . C(6) H(6A) 0.990 yes . . C(6) H(6B) 0.990 yes . . C(7) H(7A) 0.990 yes . . C(7) H(7B) 0.990 yes . . C(8) H(8A) 0.990 yes . . C(8) H(8B) 0.990 yes . . C(9) H(9A) 0.990 yes . . C(9) H(9B) 0.990 yes . . C(10) H(10) 1.000 yes . . C(11) H(11A) 0.980 yes . . C(11) H(11B) 0.980 yes . . C(11) H(11C) 0.980 yes . . C(13) H(13A) 0.990 yes . . C(13) H(13B) 0.990 yes . . C(14) H(14) 1.000 yes . . 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(10) O(3) C(12) 117.92(12) yes . . . O(1) C(1) C(2) 111.11(13) yes . . . O(1) C(1) C(14) 107.81(13) yes . . . C(2) C(1) C(14) 111.39(13) yes . . . C(1) C(2) C(3) 110.95(15) yes . . . C(2) C(3) C(4) 112.73(14) yes . . . O(2) C(4) C(3) 121.38(15) yes . . . O(2) C(4) C(5) 121.19(14) yes . . . C(3) C(4) C(5) 117.32(14) yes . . . C(4) C(5) C(6) 110.89(13) yes . . . C(4) C(5) C(14) 112.75(13) yes . . . C(6) C(5) C(14) 115.08(13) yes . . . C(5) C(6) C(7) 115.53(14) yes . . . C(6) C(7) C(8) 113.61(14) yes . . . C(7) C(8) C(9) 115.95(14) yes . . . C(8) C(9) C(10) 117.66(14) yes . . . O(3) C(10) C(9) 111.05(13) yes . . . O(3) C(10) C(11) 104.58(13) yes . . . C(9) C(10) C(11) 114.35(14) yes . . . O(3) C(12) O(4) 123.99(14) yes . . . O(3) C(12) C(13) 111.97(14) yes . . . O(4) C(12) C(13) 124.03(14) yes . . . C(12) C(13) C(14) 117.31(13) yes . . . C(1) C(14) C(5) 111.56(13) yes . . . C(1) C(14) C(13) 108.46(13) yes . . . C(5) C(14) C(13) 113.07(13) yes . . . C(1) O(1) H(1A) 107.1(18) yes . . . O(1) C(1) H(1) 108.827 yes . . . C(2) C(1) H(1) 108.825 yes . . . C(14) C(1) H(1) 108.820 yes . . . C(1) C(2) H(2A) 109.451 yes . . . C(1) C(2) H(2B) 109.443 yes . . . C(3) C(2) H(2A) 109.455 yes . . . C(3) C(2) H(2B) 109.446 yes . . . H(2A) C(2) H(2B) 108.042 yes . . . C(2) C(3) H(3A) 109.047 yes . . . C(2) C(3) H(3B) 109.046 yes . . . C(4) C(3) H(3A) 109.046 yes . . . C(4) C(3) H(3B) 109.048 yes . . . H(3A) C(3) H(3B) 107.803 yes . . . C(4) C(5) H(5) 105.760 yes . . . C(6) C(5) H(5) 105.759 yes . . . C(14) C(5) H(5) 105.760 yes . . . C(5) C(6) H(6A) 108.399 yes . . . C(5) C(6) H(6B) 108.404 yes . . . C(7) C(6) H(6A) 108.385 yes . . . C(7) C(6) H(6B) 108.390 yes . . . H(6A) C(6) H(6B) 107.457 yes . . . C(6) C(7) H(7A) 108.840 yes . . . C(6) C(7) H(7B) 108.839 yes . . . C(8) C(7) H(7A) 108.850 yes . . . C(8) C(7) H(7B) 108.842 yes . . . H(7A) C(7) H(7B) 107.695 yes . . . C(7) C(8) H(8A) 108.298 yes . . . C(7) C(8) H(8B) 108.296 yes . . . C(9) C(8) H(8A) 108.293 yes . . . C(9) C(8) H(8B) 108.295 yes . . . H(8A) C(8) H(8B) 107.403 yes . . . C(8) C(9) H(9A) 107.887 yes . . . C(8) C(9) H(9B) 107.893 yes . . . C(10) C(9) H(9A) 107.883 yes . . . C(10) C(9) H(9B) 107.894 yes . . . H(9A) C(9) H(9B) 107.192 yes . . . O(3) C(10) H(10) 108.887 yes . . . C(9) C(10) H(10) 108.896 yes . . . C(11) C(10) H(10) 108.899 yes . . . C(10) C(11) H(11A) 109.473 yes . . . C(10) C(11) H(11B) 109.470 yes . . . C(10) C(11) H(11C) 109.468 yes . . . H(11A) C(11) H(11B) 109.471 yes . . . H(11A) C(11) H(11C) 109.474 yes . . . H(11B) C(11) H(11C) 109.470 yes . . . C(12) C(13) H(13A) 107.973 yes . . . C(12) C(13) H(13B) 107.973 yes . . . C(14) C(13) H(13A) 107.975 yes . . . C(14) C(13) H(13B) 107.974 yes . . . H(13A) C(13) H(13B) 107.226 yes . . . C(1) C(14) H(14) 107.849 yes . . . C(5) C(14) H(14) 107.854 yes . . . C(13) C(14) H(14) 107.854 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_publ_flag _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 C(10) O(3) C(12) O(4) -10.7(2) no . . . . C(12) O(3) C(10) C(9) -72.38(16) no . . . . O(1) C(1) C(2) C(3) 60.41(16) no . . . . O(1) C(1) C(14) C(5) -65.80(15) no . . . . O(1) C(1) C(14) C(13) 59.38(15) no . . . . C(2) C(1) C(14) C(5) 56.35(16) no . . . . C(14) C(1) C(2) C(3) -59.81(16) no . . . . C(1) C(2) C(3) C(4) 52.67(17) no . . . . C(2) C(3) C(4) O(2) 139.43(15) no . . . . C(2) C(3) C(4) C(5) -44.32(19) no . . . . O(2) C(4) C(5) C(6) -12.2(2) no . . . . O(2) C(4) C(5) C(14) -142.92(14) no . . . . C(3) C(4) C(5) C(14) 40.82(18) no . . . . C(4) C(5) C(6) C(7) -70.58(16) no . . . . C(4) C(5) C(14) C(1) -45.73(15) no . . . . C(6) C(5) C(14) C(13) 63.14(16) no . . . . C(14) C(5) C(6) C(7) 58.89(17) no . . . . C(5) C(6) C(7) C(8) -159.37(12) no . . . . C(6) C(7) C(8) C(9) 55.12(19) no . . . . C(7) C(8) C(9) C(10) 58.12(19) no . . . . C(8) C(9) C(10) O(3) -60.98(18) no . . . . C(8) C(9) C(10) C(11) 57.07(18) no . . . . O(3) C(12) C(13) C(14) -47.64(19) no . . . . O(4) C(12) C(13) C(14) 133.36(16) no . . . . C(12) C(13) C(14) C(5) -64.08(17) no . . . . 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(3) 2.933(2) yes . . O(1) C(4) 3.424(2) yes . . O(1) C(5) 2.9670(20) yes . . O(1) C(13) 2.8335(19) yes . . O(2) C(2) 3.559(2) yes . . O(2) C(6) 2.7466(20) yes . . O(2) C(7) 3.1755(19) yes . . O(3) C(5) 3.5565(19) yes . . O(3) C(6) 3.1430(20) yes . . O(3) C(7) 2.9223(20) yes . . O(3) C(8) 3.093(2) yes . . O(3) C(14) 2.9150(18) yes . . O(4) C(6) 3.566(2) yes . . O(4) C(9) 3.168(2) yes . . O(4) C(10) 2.731(2) yes . . C(1) C(4) 2.923(2) yes . . C(2) C(5) 2.980(2) yes . . C(3) C(14) 2.982(2) yes . . C(4) C(7) 3.188(2) yes . . C(5) C(12) 3.201(2) yes . . C(6) C(9) 3.103(2) yes . . C(6) C(12) 3.033(2) yes . . C(6) C(13) 3.169(2) yes . . C(7) C(10) 3.198(2) yes . . C(7) C(12) 3.456(2) yes . . C(7) C(14) 3.167(2) yes . . C(8) C(11) 3.142(3) yes . . C(9) C(12) 3.066(2) yes . . O(1) O(4) 2.8791(17) yes . 2_557 O(1) C(12) 3.425(2) yes . 2_557 O(1) C(13) 3.590(2) yes . 2_457 O(1) C(13) 3.475(2) yes . 2_557 O(2) C(2) 3.357(2) yes . 1_455 O(2) C(3) 3.443(2) yes . 2_447 O(2) C(9) 3.514(2) yes . 3_646 O(2) C(11) 3.482(2) yes . 3_746 O(4) O(1) 2.8791(17) yes . 2_457 C(2) O(2) 3.357(2) yes . 1_655 C(3) O(2) 3.443(2) yes . 2_547 C(9) O(2) 3.514(2) yes . 3_656 C(11) O(2) 3.482(2) yes . 3_756 C(12) O(1) 3.425(2) yes . 2_457 C(13) O(1) 3.475(2) yes . 2_457 C(13) O(1) 3.590(2) yes . 2_557 O(1) H(2A) 2.6541 yes . . O(1) H(2B) 3.2838 yes . . O(1) H(3B) 2.6722 yes . . O(1) H(5) 2.6689 yes . . O(1) H(13A) 2.5115 yes . . O(1) H(13B) 3.0091 yes . . O(1) H(14) 3.2514 yes . . O(2) H(3A) 2.4798 yes . . O(2) H(3B) 2.8825 yes . . O(2) H(5) 2.8866 yes . . O(2) H(6B) 2.4998 yes . . O(2) H(7A) 3.5463 yes . . O(2) H(7B) 2.7018 yes . . O(3) H(6A) 2.7284 yes . . O(3) H(7A) 2.4084 yes . . O(3) H(8B) 3.4634 yes . . O(3) H(9A) 3.3061 yes . . O(3) H(9B) 2.6618 yes . . O(3) H(11A) 2.5361 yes . . O(3) H(11B) 2.5531 yes . . O(3) H(11C) 3.2312 yes . . O(3) H(13A) 3.1717 yes . . O(3) H(13B) 2.6731 yes . . O(3) H(14) 2.6014 yes . . O(4) H(6A) 2.6833 yes . . O(4) H(9B) 2.6261 yes . . O(4) H(10) 2.5160 yes . . O(4) H(13A) 2.5032 yes . . O(4) H(13B) 2.9332 yes . . C(1) H(3A) 3.3515 yes . . C(1) H(3B) 2.7605 yes . . C(1) H(5) 2.7730 yes . . C(1) H(13A) 2.7090 yes . . C(1) H(13B) 2.5815 yes . . C(2) H(5) 3.3702 yes . . C(2) H(14) 2.7141 yes . . C(2) H(1A) 2.56(3) yes . . C(3) H(1) 3.3610 yes . . C(3) H(5) 2.8667 yes . . C(3) H(14) 3.3151 yes . . C(3) H(1A) 3.19(3) yes . . C(4) H(2A) 3.3572 yes . . C(4) H(2B) 2.7820 yes . . C(4) H(6A) 3.3562 yes . . C(4) H(6B) 2.6382 yes . . C(4) H(7A) 3.3021 yes . . C(4) H(7B) 3.0354 yes . . C(4) H(14) 2.8456 yes . . C(5) H(1) 3.4044 yes . . C(5) H(2B) 3.2882 yes . . C(5) H(3A) 3.4024 yes . . C(5) H(3B) 2.9219 yes . . C(5) H(7A) 2.6624 yes . . C(5) H(7B) 2.9404 yes . . C(5) H(13A) 2.7463 yes . . C(5) H(13B) 3.4114 yes . . C(6) H(8A) 2.8064 yes . . C(6) H(8B) 3.4009 yes . . C(6) H(9B) 2.7987 yes . . C(6) H(13A) 3.4434 yes . . C(6) H(14) 2.7658 yes . . C(7) H(5) 3.4061 yes . . C(7) H(9A) 3.4188 yes . . C(7) H(9B) 2.8210 yes . . C(7) H(11A) 3.2723 yes . . C(7) H(14) 2.7998 yes . . C(8) H(6A) 2.6146 yes . . C(8) H(6B) 2.9010 yes . . C(8) H(10) 3.4428 yes . . C(8) H(11A) 2.8511 yes . . C(8) H(11C) 3.3791 yes . . C(9) H(6A) 2.6245 yes . . C(9) H(6B) 3.5918 yes . . C(9) H(7A) 2.8496 yes . . C(9) H(7B) 3.4266 yes . . C(9) H(11A) 2.7721 yes . . C(9) H(11B) 3.3778 yes . . C(9) H(11C) 2.7333 yes . . C(10) H(6A) 3.2028 yes . . C(10) H(7A) 2.9492 yes . . C(10) H(8A) 3.4257 yes . . C(10) H(8B) 2.8440 yes . . C(11) H(7A) 3.2983 yes . . C(11) H(8B) 2.8626 yes . . C(11) H(9A) 2.7728 yes . . C(11) H(9B) 3.3732 yes . . C(12) H(5) 3.3907 yes . . C(12) H(6A) 2.3909 yes . . C(12) H(7A) 3.1497 yes . . C(12) H(9B) 2.7956 yes . . C(12) H(10) 2.5820 yes . . C(12) H(14) 2.7751 yes . . C(13) H(1) 2.6608 yes . . C(13) H(5) 2.6839 yes . . C(13) H(6A) 2.8573 yes . . C(13) H(7A) 3.4144 yes . . C(13) H(1A) 3.59(3) yes . . C(14) H(2A) 3.3718 yes . . C(14) H(2B) 2.7236 yes . . C(14) H(3B) 3.3983 yes . . C(14) H(6A) 2.8148 yes . . C(14) H(6B) 3.4304 yes . . C(14) H(7A) 2.7214 yes . . C(14) H(1A) 3.14(3) yes . . H(1) H(2A) 2.3633 yes . . H(1) H(2B) 2.3609 yes . . H(1) H(13A) 3.0015 yes . . H(1) H(13B) 2.3610 yes . . H(1) H(14) 2.3491 yes . . H(1) H(1A) 2.1964 yes . . H(2A) H(3A) 2.3954 yes . . H(2A) H(3B) 2.3244 yes . . H(2A) H(1A) 2.4412 yes . . H(2B) H(3A) 2.3283 yes . . H(2B) H(3B) 2.8627 yes . . H(2B) H(14) 2.5395 yes . . H(2B) H(1A) 3.4495 yes . . H(3B) H(5) 2.8525 yes . . H(3B) H(1A) 2.8274 yes . . H(5) H(6A) 2.2827 yes . . H(5) H(6B) 2.3380 yes . . H(5) H(7A) 3.5676 yes . . H(5) H(13A) 2.4722 yes . . H(5) H(13B) 3.5561 yes . . H(5) H(14) 2.8615 yes . . H(5) H(1A) 3.4641 yes . . H(6A) H(7A) 2.5066 yes . . H(6A) H(7B) 2.8484 yes . . H(6A) H(8A) 2.8840 yes . . H(6A) H(8B) 3.5346 yes . . H(6A) H(9A) 3.5149 yes . . H(6A) H(9B) 2.0909 yes . . H(6A) H(13A) 3.0498 yes . . H(6A) H(14) 3.0767 yes . . H(6B) H(7A) 2.8499 yes . . H(6B) H(7B) 2.2749 yes . . H(6B) H(8A) 2.7934 yes . . H(6B) H(9B) 3.1990 yes . . H(7A) H(8A) 2.8610 yes . . H(7A) H(8B) 2.3338 yes . . H(7A) H(9B) 3.2050 yes . . H(7A) H(11A) 2.7178 yes . . H(7A) H(14) 2.1037 yes . . H(7B) H(8A) 2.3286 yes . . H(7B) H(8B) 2.3668 yes . . H(7B) H(14) 3.2824 yes . . H(8A) H(9A) 2.3347 yes . . H(8A) H(9B) 2.3350 yes . . H(8B) H(9A) 2.3388 yes . . H(8B) H(9B) 2.8562 yes . . H(8B) H(11A) 2.4006 yes . . H(8B) H(11C) 2.9686 yes . . H(9A) H(10) 2.3280 yes . . H(9A) H(11A) 3.1235 yes . . H(9A) H(11C) 2.5962 yes . . H(9B) H(10) 2.3378 yes . . H(10) H(11A) 2.8593 yes . . H(10) H(11B) 2.3314 yes . . H(10) H(11C) 2.3853 yes . . H(13A) H(14) 2.8684 yes . . H(13A) H(1A) 3.2743 yes . . H(13B) H(14) 2.3956 yes . . O(1) H(1) 3.5676 yes . 2_457 O(1) H(5) 3.0294 yes . 2_557 O(1) H(6A) 3.0609 yes . 2_557 O(1) H(8B) 3.3710 yes . 4_655 O(1) H(13A) 2.7634 yes . 2_557 O(1) H(13B) 2.6553 yes . 2_457 O(2) H(1) 3.2805 yes . 1_455 O(2) H(2A) 3.3341 yes . 1_455 O(2) H(2A) 3.2793 yes . 2_447 O(2) H(2B) 2.6578 yes . 1_455 O(2) H(3A) 2.6276 yes . 2_447 O(2) H(9A) 2.5817 yes . 3_646 O(2) H(11B) 2.7556 yes . 3_746 O(2) H(11C) 3.3414 yes . 3_746 O(2) H(11C) 3.5549 yes . 4_655 O(3) H(7B) 3.5107 yes . 3_756 O(4) H(1) 3.4929 yes . 2_457 O(4) H(2A) 3.3943 yes . 2_457 O(4) H(7A) 3.4679 yes . 3_756 O(4) H(8A) 2.8826 yes . 3_656 O(4) H(8B) 3.5078 yes . 3_756 O(4) H(11A) 2.6995 yes . 3_756 O(4) H(1A) 2.04(3) yes . 2_457 C(1) H(5) 3.5578 yes . 1_655 C(1) H(6B) 3.1500 yes . 1_655 C(1) H(13A) 2.9557 yes . 2_557 C(2) H(3A) 3.1612 yes . 2_547 C(2) H(11C) 3.4106 yes . 3_746 C(2) H(11C) 3.5996 yes . 4_755 C(3) H(2B) 3.4640 yes . 2_447 C(3) H(8B) 3.2787 yes . 4_655 C(3) H(9A) 3.1795 yes . 4_655 C(3) H(11C) 3.3054 yes . 3_746 C(3) H(11C) 3.0593 yes . 4_655 C(4) H(1) 3.3221 yes . 1_455 C(4) H(2B) 3.4742 yes . 1_455 C(4) H(3A) 3.5619 yes . 2_447 C(4) H(11B) 3.2523 yes . 3_746 C(4) H(11C) 3.3888 yes . 3_746 C(4) H(11C) 3.5931 yes . 4_655 C(5) H(1) 3.1408 yes . 1_455 C(5) H(13A) 3.5514 yes . 2_457 C(6) H(1) 3.1579 yes . 1_455 C(6) H(13B) 3.5028 yes . 1_455 C(6) H(14) 3.4769 yes . 1_455 C(7) H(9B) 3.5611 yes . 3_646 C(7) H(10) 3.2096 yes . 3_746 C(7) H(11B) 3.5077 yes . 3_746 C(8) H(3B) 3.0868 yes . 4_654 C(8) H(11B) 3.3168 yes . 1_455 C(9) H(3B) 3.2506 yes . 4_654 C(9) H(7B) 3.2309 yes . 3_656 C(9) H(11B) 3.0481 yes . 1_455 C(10) H(7A) 3.4193 yes . 3_756 C(10) H(7B) 3.4655 yes . 3_756 C(11) H(2A) 2.9492 yes . 4_754 C(11) H(2B) 3.4510 yes . 3_756 C(11) H(3B) 3.1894 yes . 4_654 C(11) H(7B) 3.4479 yes . 3_756 C(11) H(8A) 3.1412 yes . 1_655 C(11) H(9A) 3.4635 yes . 1_655 C(12) H(11A) 3.5948 yes . 3_756 C(12) H(1A) 2.73(3) yes . 2_457 C(13) H(1) 3.2598 yes . 2_457 C(13) H(5) 3.1512 yes . 2_557 C(13) H(6B) 3.5239 yes . 1_655 C(13) H(1A) 3.06(3) yes . 2_457 C(14) H(6B) 3.1499 yes . 1_655 H(1) O(1) 3.5676 yes . 2_557 H(1) O(2) 3.2805 yes . 1_655 H(1) O(4) 3.4929 yes . 2_557 H(1) C(4) 3.3221 yes . 1_655 H(1) C(5) 3.1408 yes . 1_655 H(1) C(6) 3.1579 yes . 1_655 H(1) C(13) 3.2598 yes . 2_557 H(1) H(5) 2.5651 yes . 1_655 H(1) H(5) 3.5905 yes . 2_557 H(1) H(6A) 3.3934 yes . 1_655 H(1) H(6B) 2.5067 yes . 1_655 H(1) H(13A) 2.2924 yes . 2_557 H(2A) O(2) 3.3341 yes . 1_655 H(2A) O(2) 3.2793 yes . 2_547 H(2A) O(4) 3.3943 yes . 2_557 H(2A) C(11) 2.9492 yes . 4_755 H(2A) H(3A) 2.9438 yes . 2_547 H(2A) H(8A) 3.3519 yes . 4_655 H(2A) H(8B) 3.4659 yes . 4_655 H(2A) H(9A) 3.2581 yes . 4_655 H(2A) H(11A) 2.8455 yes . 4_755 H(2A) H(11B) 2.7970 yes . 4_755 H(2A) H(11C) 2.7010 yes . 4_755 H(2B) O(2) 2.6578 yes . 1_655 H(2B) C(3) 3.4640 yes . 2_547 H(2B) C(4) 3.4742 yes . 1_655 H(2B) C(11) 3.4510 yes . 3_746 H(2B) H(3A) 2.5517 yes . 2_547 H(2B) H(6B) 3.1820 yes . 1_655 H(2B) H(9A) 3.2902 yes . 3_746 H(2B) H(10) 3.2118 yes . 3_746 H(2B) H(11C) 2.6868 yes . 3_746 H(3A) O(2) 2.6276 yes . 2_547 H(3A) C(2) 3.1612 yes . 2_447 H(3A) C(4) 3.5619 yes . 2_547 H(3A) H(2A) 2.9438 yes . 2_447 H(3A) H(2B) 2.5517 yes . 2_447 H(3A) H(3A) 3.3924 yes . 2_447 H(3A) H(3A) 3.3924 yes . 2_547 H(3A) H(8B) 3.5954 yes . 4_655 H(3A) H(9A) 2.8133 yes . 4_655 H(3A) H(11B) 3.5021 yes . 3_746 H(3A) H(11C) 2.8303 yes . 3_746 H(3A) H(11C) 2.7894 yes . 4_655 H(3B) C(8) 3.0868 yes . 4_655 H(3B) C(9) 3.2506 yes . 4_655 H(3B) C(11) 3.1894 yes . 4_655 H(3B) H(8A) 3.3170 yes . 4_655 H(3B) H(8B) 2.3500 yes . 4_655 H(3B) H(9A) 2.7338 yes . 4_655 H(3B) H(11A) 3.0829 yes . 4_655 H(3B) H(11C) 2.5511 yes . 4_655 H(5) O(1) 3.0294 yes . 2_457 H(5) C(1) 3.5578 yes . 1_455 H(5) C(13) 3.1512 yes . 2_457 H(5) H(1) 2.5651 yes . 1_455 H(5) H(1) 3.5905 yes . 2_457 H(5) H(13A) 2.5634 yes . 2_457 H(5) H(13B) 2.8161 yes . 2_457 H(5) H(1A) 3.2138 yes . 2_457 H(6A) O(1) 3.0609 yes . 2_457 H(6A) H(1) 3.3934 yes . 1_455 H(6A) H(13B) 3.1079 yes . 1_455 H(6A) H(1A) 2.7747 yes . 2_457 H(6B) C(1) 3.1500 yes . 1_455 H(6B) C(13) 3.5239 yes . 1_455 H(6B) C(14) 3.1499 yes . 1_455 H(6B) H(1) 2.5067 yes . 1_455 H(6B) H(2B) 3.1820 yes . 1_455 H(6B) H(10) 3.5913 yes . 3_646 H(6B) H(13B) 3.0048 yes . 1_455 H(6B) H(14) 2.5270 yes . 1_455 H(7A) O(4) 3.4679 yes . 3_746 H(7A) C(10) 3.4193 yes . 3_746 H(7A) H(10) 2.5543 yes . 3_746 H(7A) H(11B) 3.4821 yes . 3_746 H(7B) O(3) 3.5107 yes . 3_746 H(7B) C(9) 3.2309 yes . 3_646 H(7B) C(10) 3.4655 yes . 3_746 H(7B) C(11) 3.4479 yes . 3_746 H(7B) H(9A) 2.9138 yes . 3_646 H(7B) H(9B) 2.6439 yes . 3_646 H(7B) H(10) 2.9519 yes . 3_746 H(7B) H(11B) 2.6968 yes . 3_746 H(8A) O(4) 2.8826 yes . 3_646 H(8A) C(11) 3.1412 yes . 1_455 H(8A) H(2A) 3.3519 yes . 4_654 H(8A) H(3B) 3.3170 yes . 4_654 H(8A) H(9B) 3.5700 yes . 3_646 H(8A) H(11A) 2.7202 yes . 1_455 H(8A) H(11B) 2.6844 yes . 1_455 H(8A) H(1A) 3.2114 yes . 4_654 H(8B) O(1) 3.3710 yes . 4_654 H(8B) O(4) 3.5078 yes . 3_746 H(8B) C(3) 3.2787 yes . 4_654 H(8B) H(2A) 3.4659 yes . 4_654 H(8B) H(3A) 3.5954 yes . 4_654 H(8B) H(3B) 2.3500 yes . 4_654 H(8B) H(1A) 3.0296 yes . 4_654 H(9A) O(2) 2.5817 yes . 3_656 H(9A) C(3) 3.1795 yes . 4_654 H(9A) C(11) 3.4635 yes . 1_455 H(9A) H(2A) 3.2581 yes . 4_654 H(9A) H(2B) 3.2902 yes . 3_756 H(9A) H(3A) 2.8133 yes . 4_654 H(9A) H(3B) 2.7338 yes . 4_654 H(9A) H(7B) 2.9138 yes . 3_656 H(9A) H(11B) 2.5344 yes . 1_455 H(9B) C(7) 3.5611 yes . 3_656 H(9B) H(7B) 2.6439 yes . 3_656 H(9B) H(8A) 3.5700 yes . 3_656 H(9B) H(11B) 2.8962 yes . 1_455 H(9B) H(1A) 3.5261 yes . 2_457 H(10) C(7) 3.2096 yes . 3_756 H(10) H(2B) 3.2118 yes . 3_756 H(10) H(6B) 3.5913 yes . 3_656 H(10) H(7A) 2.5543 yes . 3_756 H(10) H(7B) 2.9519 yes . 3_756 H(10) H(14) 2.9787 yes . 3_756 H(11A) O(4) 2.6995 yes . 3_746 H(11A) C(12) 3.5948 yes . 3_746 H(11A) H(2A) 2.8455 yes . 4_754 H(11A) H(3B) 3.0829 yes . 4_654 H(11A) H(8A) 2.7202 yes . 1_655 H(11B) O(2) 2.7556 yes . 3_756 H(11B) C(4) 3.2523 yes . 3_756 H(11B) C(7) 3.5077 yes . 3_756 H(11B) C(8) 3.3168 yes . 1_655 H(11B) C(9) 3.0481 yes . 1_655 H(11B) H(2A) 2.7970 yes . 4_754 H(11B) H(3A) 3.5021 yes . 3_756 H(11B) H(7A) 3.4821 yes . 3_756 H(11B) H(7B) 2.6968 yes . 3_756 H(11B) H(8A) 2.6844 yes . 1_655 H(11B) H(9A) 2.5344 yes . 1_655 H(11B) H(9B) 2.8962 yes . 1_655 H(11C) O(2) 3.3414 yes . 3_756 H(11C) O(2) 3.5549 yes . 4_654 H(11C) C(2) 3.4106 yes . 3_756 H(11C) C(2) 3.5996 yes . 4_754 H(11C) C(3) 3.3054 yes . 3_756 H(11C) C(3) 3.0593 yes . 4_654 H(11C) C(4) 3.3888 yes . 3_756 H(11C) C(4) 3.5931 yes . 4_654 H(11C) H(2A) 2.7010 yes . 4_754 H(11C) H(2B) 2.6868 yes . 3_756 H(11C) H(3A) 2.8303 yes . 3_756 H(11C) H(3A) 2.7894 yes . 4_654 H(11C) H(3B) 2.5511 yes . 4_654 H(13A) O(1) 2.7634 yes . 2_457 H(13A) C(1) 2.9557 yes . 2_457 H(13A) C(5) 3.5514 yes . 2_557 H(13A) H(1) 2.2924 yes . 2_457 H(13A) H(5) 2.5634 yes . 2_557 H(13A) H(13B) 3.1392 yes . 2_457 H(13A) H(1A) 2.4877 yes . 2_457 H(13B) O(1) 2.6553 yes . 2_557 H(13B) C(6) 3.5028 yes . 1_655 H(13B) H(5) 2.8161 yes . 2_557 H(13B) H(6A) 3.1079 yes . 1_655 H(13B) H(6B) 3.0048 yes . 1_655 H(13B) H(13A) 3.1392 yes . 2_557 H(13B) H(1A) 3.0395 yes . 2_557 H(14) C(6) 3.4769 yes . 1_655 H(14) H(6B) 2.5270 yes . 1_655 H(14) H(10) 2.9787 yes . 3_746 H(1A) O(4) 2.04(3) yes . 2_557 H(1A) C(12) 2.73(3) yes . 2_557 H(1A) C(13) 3.06(3) yes . 2_557 H(1A) H(5) 3.2138 yes . 2_557 H(1A) H(6A) 2.7747 yes . 2_557 H(1A) H(8A) 3.2114 yes . 4_655 H(1A) H(8B) 3.0296 yes . 4_655 H(1A) H(9B) 3.5261 yes . 2_557 H(1A) H(13A) 2.4877 yes . 2_557 H(1A) H(13B) 3.0395 yes . 2_457 #============================================================================== loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_D _geom_hbond_site_symmetry_H _geom_hbond_site_symmetry_A _geom_hbond_distance_DA _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_angle_DHA _geom_hbond_publ_flag O(1) H(1A) O(4) . . 2_557 2.8791(17) 0.862 2.04(3) 163(2) no #============================================================================== # 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 #============================================================================== # Attachment '- (i)-Sch-642305.cif' data__ad04 _database_code_depnum_ccdc_archive 'CCDC 820821' #TrackingRef '- (i)-Sch-642305.cif' _audit_creation_date 2010-06-08 _audit_creation_method 'by CrystalStructure 3.8' _audit_update_record ? #============================================================================== # CHEMICAL DATA _chemical_formula_sum 'C14 H20 O4 ' _chemical_formula_moiety 'C14 H20 O4 ' _chemical_formula_weight 252.31 _chemical_melting_point ? #============================================================================== # CRYSTAL DATA _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' _symmetry_space_group_name_Hall 'P 2ac 2ab' _symmetry_Int_Tables_number 19 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 +X,+Y,+Z 2 1/2+X,1/2-Y,-Z 3 -X,1/2+Y,1/2-Z 4 1/2-X,-Y,1/2+Z #------------------------------------------------------------------------------ _cell_length_a 6.14187(12) _cell_length_b 11.3932(2) _cell_length_c 18.2633(4) _cell_angle_alpha 90.0000 _cell_angle_beta 90.0000 _cell_angle_gamma 90.0000 _cell_volume 1277.98(4) _cell_formula_units_Z 4 _cell_measurement_reflns_used 7257 _cell_measurement_theta_min 7.2 _cell_measurement_theta_max 68.2 _cell_measurement_temperature 93.1 #------------------------------------------------------------------------------ _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.10 _exptl_crystal_density_diffrn 1.311 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 544.00 _exptl_absorpt_coefficient_mu 0.781 _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 0.770 _exptl_absorpt_correction_T_max 0.925 #============================================================================== # 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 10.00 _diffrn_reflns_number 7709 _diffrn_reflns_av_R_equivalents 0.043 _diffrn_reflns_theta_max 68.19 _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 68.19 _diffrn_measured_fraction_theta_full 0.985 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 18 #============================================================================== # 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 2219 _reflns_number_gt 1910 _reflns_threshold_expression F^2^>2.0\s(F^2^) _refine_ls_structure_factor_coef Fsqd _refine_ls_R_factor_gt 0.0378 _refine_ls_wR_factor_ref 0.0987 _refine_ls_hydrogen_treatment refall _refine_ls_number_reflns 2219 _refine_ls_number_parameters 168 _refine_ls_goodness_of_fit_ref 1.086 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.0332P)^2^+0.5629P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_shift/su_max 0.0000 _refine_diff_density_max 0.27 _refine_diff_density_min -0.24 _refine_ls_extinction_method none _refine_ls_extinction_coef ? _chemical_absolute_configuration ad _refine_ls_abs_structure_details 'Flack, H. D. (1983), Acta Cryst. A39, 876-881. 857 Friedel Pairs' _refine_ls_abs_structure_Flack -0.2(2) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source O O 0.049 0.032 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; 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) ; #============================================================================== # 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 0.4866(2) 0.63721(16) -0.05079(9) 0.0259(3) Uani 1.00 1 d . . . O(2) O 0.9658(2) 0.37861(15) 0.06134(9) 0.0312(4) Uani 1.00 1 d . . . O(3) O 0.5109(2) 0.71260(13) 0.22021(8) 0.0207(3) Uani 1.00 1 d . . . O(4) O 0.6829(2) 0.86625(15) 0.16901(9) 0.0265(4) Uani 1.00 1 d . . . C(1) C 0.4088(3) 0.5628(2) 0.00741(12) 0.0222(5) Uani 1.00 1 d . . . C(2) C 0.4432(4) 0.4366(2) -0.01290(12) 0.0262(5) Uani 1.00 1 d . . . C(3) C 0.6228(4) 0.3786(2) 0.00563(13) 0.0284(5) Uani 1.00 1 d . . . C(4) C 0.7976(3) 0.4325(2) 0.04875(13) 0.0229(5) Uani 1.00 1 d . . . C(5) C 0.7697(3) 0.5588(2) 0.07461(12) 0.0195(5) Uani 1.00 1 d . . . C(6) C 0.8995(3) 0.5791(2) 0.14542(12) 0.0215(5) Uani 1.00 1 d . . . C(7) C 0.8128(3) 0.5142(2) 0.21271(13) 0.0213(5) Uani 1.00 1 d . . . C(8) C 0.8887(3) 0.5668(2) 0.28562(13) 0.0250(5) Uani 1.00 1 d . . . C(9) C 0.8435(3) 0.6983(2) 0.29578(14) 0.0236(5) Uani 1.00 1 d . . . C(10) C 0.6057(3) 0.7382(2) 0.29266(13) 0.0218(5) Uani 1.00 1 d . . . C(11) C 0.4583(3) 0.6770(2) 0.34678(13) 0.0249(5) Uani 1.00 1 d . . . C(12) C 0.5757(3) 0.7776(2) 0.16312(12) 0.0196(4) Uani 1.00 1 d . . . C(13) C 0.4950(3) 0.7287(2) 0.09153(12) 0.0219(5) Uani 1.00 1 d . . . C(14) C 0.5267(3) 0.59686(19) 0.07758(12) 0.0185(4) Uani 1.00 1 d . . . H(1) H 0.2494 0.5768 0.0142 0.027 Uiso 1.00 1 c R . . H(1A) H 0.410(4) 0.623(2) -0.0845(15) 0.037(8) Uiso 1.00 1 c . . . H(2) H 0.3332 0.3968 -0.0398 0.031 Uiso 1.00 1 c R . . H(3) H 0.6385 0.2993 -0.0096 0.034 Uiso 1.00 1 c R . . H(4) H 0.8397 0.6092 0.0364 0.023 Uiso 1.00 1 c R . . H(5) H 1.0521 0.5545 0.1370 0.026 Uiso 1.00 1 c R . . H(6) H 0.9007 0.6643 0.1561 0.026 Uiso 1.00 1 c R . . H(7) H 0.8604 0.4313 0.2103 0.026 Uiso 1.00 1 c R . . H(8) H 0.6517 0.5151 0.2113 0.026 Uiso 1.00 1 c R . . H(9) H 1.0475 0.5536 0.2903 0.030 Uiso 1.00 1 c R . . H(10) H 0.8168 0.5235 0.3259 0.030 Uiso 1.00 1 c R . . H(11) H 0.9039 0.7223 0.3437 0.028 Uiso 1.00 1 c R . . H(12) H 0.9250 0.7415 0.2576 0.028 Uiso 1.00 1 c R . . H(13) H 0.5992 0.8247 0.3015 0.026 Uiso 1.00 1 c R . . H(14) H 0.5682 0.7720 0.0515 0.026 Uiso 1.00 1 c R . . H(15) H 0.3374 0.7460 0.0879 0.026 Uiso 1.00 1 c R . . H(16) H 0.4564 0.5535 0.1189 0.022 Uiso 1.00 1 c R . . H(17) H 0.4842 0.5922 0.3448 0.030 Uiso 1.00 1 c R . . H(18) H 0.3060 0.6934 0.3344 0.030 Uiso 1.00 1 c R . . H(19) H 0.4891 0.7058 0.3963 0.030 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) 0.0245(8) 0.0330(9) 0.0200(8) -0.0050(8) -0.0039(7) 0.0041(7) O(2) 0.0321(9) 0.0302(9) 0.0313(9) 0.0112(9) -0.0027(7) -0.0054(7) O(3) 0.0186(7) 0.0233(8) 0.0202(8) -0.0011(7) -0.0010(6) -0.0008(6) O(4) 0.0298(8) 0.0212(8) 0.0283(9) -0.0012(8) 0.0044(7) -0.0011(7) C(1) 0.0162(10) 0.0297(13) 0.0206(12) -0.0034(10) -0.0015(9) 0.0027(11) C(2) 0.0289(12) 0.0283(13) 0.0215(12) -0.0107(12) -0.0021(10) -0.0009(11) C(3) 0.0347(13) 0.0259(13) 0.0246(13) -0.0018(12) 0.0009(10) -0.0027(12) C(4) 0.0242(11) 0.0254(13) 0.0190(11) 0.0009(11) 0.0042(10) 0.0023(10) C(5) 0.0177(10) 0.0181(12) 0.0226(12) 0.0008(10) 0.0037(9) 0.0018(10) C(6) 0.0173(10) 0.0247(12) 0.0225(12) 0.0000(10) 0.0002(9) -0.0034(10) C(7) 0.0194(10) 0.0195(12) 0.0250(12) 0.0016(9) -0.0013(10) 0.0007(10) C(8) 0.0209(11) 0.0297(13) 0.0243(12) 0.0051(10) -0.0039(10) -0.0002(11) C(9) 0.0181(11) 0.0280(14) 0.0249(13) -0.0036(10) -0.0009(9) -0.0012(11) C(10) 0.0229(11) 0.0211(12) 0.0215(12) 0.0013(10) -0.0011(10) -0.0040(10) C(11) 0.0235(12) 0.0306(13) 0.0205(12) -0.0006(11) 0.0036(10) 0.0006(11) C(12) 0.0174(10) 0.0186(11) 0.0230(12) 0.0026(10) 0.0036(9) -0.0003(10) C(13) 0.0178(11) 0.0244(12) 0.0235(11) 0.0008(11) -0.0002(9) 0.0025(10) C(14) 0.0160(10) 0.0199(11) 0.0197(11) -0.0010(9) 0.0006(8) 0.0021(9) #============================================================================== _computing_data_collection PROCESS-AUTO _computing_cell_refinement PROCESS-AUTO _computing_data_reduction CrystalStructure _computing_structure_solution SHELXS97 _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(1) 1.441(2) yes . . O(2) C(4) 1.224(2) yes . . O(3) C(10) 1.475(2) yes . . O(3) C(12) 1.339(2) yes . . O(4) C(12) 1.210(2) yes . . C(1) C(2) 1.500(3) yes . . C(1) C(14) 1.522(3) yes . . C(2) C(3) 1.330(3) yes . . C(3) C(4) 1.466(3) yes . . C(4) C(5) 1.524(3) yes . . C(5) C(6) 1.537(3) yes . . C(5) C(14) 1.555(3) yes . . C(6) C(7) 1.530(3) yes . . C(7) C(8) 1.532(3) yes . . C(8) C(9) 1.535(3) yes . . C(9) C(10) 1.530(3) yes . . C(10) C(11) 1.511(3) yes . . C(12) C(13) 1.505(3) yes . . C(13) C(14) 1.536(3) yes . . O(1) H(1A) 0.79(2) no . . C(1) H(1) 1.000 no . . C(2) H(2) 0.950 no . . C(3) H(3) 0.950 no . . C(5) H(4) 1.000 no . . C(6) H(5) 0.990 no . . C(6) H(6) 0.990 no . . C(7) H(7) 0.990 no . . C(7) H(8) 0.990 no . . C(8) H(9) 0.990 no . . C(8) H(10) 0.990 no . . C(9) H(11) 0.990 no . . C(9) H(12) 0.990 no . . C(10) H(13) 1.000 no . . C(11) H(17) 0.980 no . . C(11) H(18) 0.980 no . . C(11) H(19) 0.980 no . . C(13) H(14) 0.990 no . . C(13) H(15) 0.990 no . . C(14) H(16) 1.000 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(10) O(3) C(12) 118.16(16) yes . . . O(1) C(1) C(2) 109.58(18) yes . . . O(1) C(1) C(14) 108.27(18) yes . . . C(2) C(1) C(14) 112.68(18) yes . . . C(1) C(2) C(3) 122.0(2) yes . . . C(2) C(3) C(4) 122.4(2) yes . . . O(2) C(4) C(3) 120.6(2) yes . . . O(2) C(4) C(5) 120.7(2) yes . . . C(3) C(4) C(5) 118.7(2) yes . . . C(4) C(5) C(6) 110.16(18) yes . . . C(4) C(5) C(14) 112.45(17) yes . . . C(6) C(5) C(14) 115.25(17) yes . . . C(5) C(6) C(7) 115.00(18) yes . . . C(6) C(7) C(8) 113.79(18) yes . . . C(7) C(8) C(9) 115.54(19) yes . . . C(8) C(9) C(10) 117.27(19) yes . . . O(3) C(10) C(9) 110.58(18) yes . . . O(3) C(10) C(11) 105.03(17) yes . . . C(9) C(10) C(11) 114.2(2) yes . . . O(3) C(12) O(4) 123.6(2) yes . . . O(3) C(12) C(13) 111.94(18) yes . . . O(4) C(12) C(13) 124.4(2) yes . . . C(12) C(13) C(14) 117.65(18) yes . . . C(1) C(14) C(5) 110.86(17) yes . . . C(1) C(14) C(13) 109.18(17) yes . . . C(5) C(14) C(13) 113.59(17) yes . . . C(1) O(1) H(1A) 105(2) no . . . O(1) C(1) H(1) 108.7 no . . . C(2) C(1) H(1) 108.7 no . . . C(14) C(1) H(1) 108.7 no . . . C(1) C(2) H(2) 119.0 no . . . C(3) C(2) H(2) 119.0 no . . . C(2) C(3) H(3) 118.8 no . . . C(4) C(3) H(3) 118.8 no . . . C(4) C(5) H(4) 106.1 no . . . C(6) C(5) H(4) 106.1 no . . . C(14) C(5) H(4) 106.1 no . . . C(5) C(6) H(5) 108.5 no . . . C(5) C(6) H(6) 108.5 no . . . C(7) C(6) H(5) 108.5 no . . . C(7) C(6) H(6) 108.5 no . . . H(5) C(6) H(6) 107.5 no . . . C(6) C(7) H(7) 108.8 no . . . C(6) C(7) H(8) 108.8 no . . . C(8) C(7) H(7) 108.8 no . . . C(8) C(7) H(8) 108.8 no . . . H(7) C(7) H(8) 107.7 no . . . C(7) C(8) H(9) 108.4 no . . . C(7) C(8) H(10) 108.4 no . . . C(9) C(8) H(9) 108.4 no . . . C(9) C(8) H(10) 108.4 no . . . H(9) C(8) H(10) 107.5 no . . . C(8) C(9) H(11) 108.0 no . . . C(8) C(9) H(12) 108.0 no . . . C(10) C(9) H(11) 108.0 no . . . C(10) C(9) H(12) 108.0 no . . . H(11) C(9) H(12) 107.2 no . . . O(3) C(10) H(13) 108.9 no . . . C(9) C(10) H(13) 108.9 no . . . C(11) C(10) H(13) 108.9 no . . . C(10) C(11) H(17) 109.5 no . . . C(10) C(11) H(18) 109.5 no . . . C(10) C(11) H(19) 109.5 no . . . H(17) C(11) H(18) 109.5 no . . . H(17) C(11) H(19) 109.5 no . . . H(18) C(11) H(19) 109.5 no . . . C(12) C(13) H(14) 107.9 no . . . C(12) C(13) H(15) 107.9 no . . . C(14) C(13) H(14) 107.9 no . . . C(14) C(13) H(15) 107.9 no . . . H(14) C(13) H(15) 107.2 no . . . C(1) C(14) H(16) 107.7 no . . . C(5) C(14) H(16) 107.7 no . . . C(13) C(14) H(16) 107.7 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(10) O(3) C(12) O(4) -11.0(3) ? . . . . C(10) O(3) C(12) C(13) 170.36(17) ? . . . . C(12) O(3) C(10) C(9) -71.9(2) ? . . . . C(12) O(3) C(10) C(11) 164.39(18) ? . . . . O(1) C(1) C(2) C(3) 92.0(2) ? . . . . O(1) C(1) C(14) C(5) -70.8(2) ? . . . . O(1) C(1) C(14) C(13) 55.0(2) ? . . . . C(2) C(1) C(14) C(5) 50.5(2) ? . . . . C(2) C(1) C(14) C(13) 176.40(18) ? . . . . C(14) C(1) C(2) C(3) -28.6(3) ? . . . . C(1) C(2) C(3) C(4) 1.6(3) ? . . . . C(2) C(3) C(4) O(2) -175.9(2) ? . . . . C(2) C(3) C(4) C(5) 1.4(3) ? . . . . O(2) C(4) C(5) C(6) -30.4(2) ? . . . . O(2) C(4) C(5) C(14) -160.4(2) ? . . . . C(3) C(4) C(5) C(6) 152.4(2) ? . . . . C(3) C(4) C(5) C(14) 22.3(2) ? . . . . C(4) C(5) C(6) C(7) -68.3(2) ? . . . . C(4) C(5) C(14) C(1) -47.5(2) ? . . . . C(4) C(5) C(14) C(13) -170.82(18) ? . . . . C(6) C(5) C(14) C(1) -174.83(18) ? . . . . C(6) C(5) C(14) C(13) 61.8(2) ? . . . . C(14) C(5) C(6) C(7) 60.2(2) ? . . . . C(5) C(6) C(7) C(8) -159.60(19) ? . . . . C(6) C(7) C(8) C(9) 54.0(2) ? . . . . C(7) C(8) C(9) C(10) 59.7(2) ? . . . . C(8) C(9) C(10) O(3) -62.0(2) ? . . . . C(8) C(9) C(10) C(11) 56.2(2) ? . . . . O(3) C(12) C(13) C(14) -48.2(2) ? . . . . O(4) C(12) C(13) C(14) 133.1(2) ? . . . . C(12) C(13) C(14) C(1) 172.71(18) ? . . . . C(12) C(13) C(14) C(5) -63.0(2) ? . . . . 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) O(4) 2.854(2) ? . 2_465 O(1) C(12) 3.394(2) ? . 2_465 O(1) C(13) 3.465(2) ? . 2_465 O(1) C(13) 3.555(2) ? . 2_565 O(2) C(1) 3.575(2) ? . 1_655 O(2) C(2) 3.297(2) ? . 1_655 O(2) C(3) 3.319(3) ? . 2_555 O(2) C(9) 3.522(3) ? . 3_745 O(4) O(1) 2.854(2) ? . 2_565 O(4) C(8) 3.582(2) ? . 3_755 C(1) O(2) 3.575(2) ? . 1_455 C(2) O(2) 3.297(2) ? . 1_455 C(3) O(2) 3.319(3) ? . 2_455 C(3) C(11) 3.576(3) ? . 3_645 C(8) O(4) 3.582(2) ? . 3_745 C(9) O(2) 3.522(3) ? . 3_755 C(11) C(3) 3.576(3) ? . 3_655 C(12) O(1) 3.394(2) ? . 2_565 C(13) O(1) 3.555(2) ? . 2_465 C(13) O(1) 3.465(2) ? . 2_565 O(1) H(4) 3.039 ? . 2_465 O(1) H(6) 3.015 ? . 2_465 O(1) H(10) 3.143 ? . 4_664 O(1) H(14) 2.770 ? . 2_465 O(1) H(15) 2.621 ? . 2_565 O(2) H(1) 2.979 ? . 1_655 O(2) H(2) 2.924 ? . 1_655 O(2) H(2) 3.266 ? . 2_555 O(2) H(3) 2.475 ? . 2_555 O(2) H(11) 2.611 ? . 3_745 O(2) H(18) 3.297 ? . 3_645 O(2) H(19) 3.505 ? . 3_645 O(2) H(19) 3.177 ? . 4_664 O(4) H(1) 3.432 ? . 2_565 O(4) H(1A) 2.09(2) ? . 2_565 O(4) H(8) 3.446 ? . 3_655 O(4) H(9) 2.802 ? . 3_755 O(4) H(10) 3.555 ? . 3_655 O(4) H(10) 3.558 ? . 3_755 O(4) H(17) 2.783 ? . 3_655 C(1) H(4) 3.575 ? . 1_455 C(1) H(5) 3.227 ? . 1_455 C(1) H(14) 3.012 ? . 2_465 C(2) H(3) 3.301 ? . 2_455 C(2) H(9) 3.596 ? . 4_664 C(2) H(10) 3.324 ? . 4_664 C(2) H(11) 3.318 ? . 4_664 C(2) H(18) 3.509 ? . 4_564 C(2) H(19) 3.409 ? . 3_645 C(2) H(19) 3.526 ? . 4_564 C(3) H(2) 3.451 ? . 2_555 C(3) H(10) 3.486 ? . 4_664 C(3) H(11) 3.176 ? . 4_664 C(3) H(19) 2.749 ? . 3_645 C(3) H(19) 3.255 ? . 4_664 C(4) H(1) 3.287 ? . 1_655 C(4) H(3) 3.446 ? . 2_555 C(4) H(11) 3.599 ? . 3_745 C(4) H(18) 3.519 ? . 3_645 C(4) H(19) 3.283 ? . 3_645 C(4) H(19) 3.458 ? . 4_664 C(5) H(1) 3.153 ? . 1_655 C(5) H(14) 3.519 ? . 2_565 C(6) H(1) 3.219 ? . 1_655 C(6) H(1A) 3.57(2) ? . 2_565 C(6) H(15) 3.457 ? . 1_655 C(6) H(16) 3.467 ? . 1_655 C(7) H(12) 3.542 ? . 3_745 C(7) H(13) 3.337 ? . 3_645 C(8) H(1A) 3.44(2) ? . 4_665 C(8) H(18) 3.073 ? . 1_655 C(9) H(3) 3.556 ? . 4_665 C(9) H(7) 3.220 ? . 3_755 C(9) H(18) 2.928 ? . 1_655 C(10) H(8) 3.530 ? . 3_655 C(11) H(2) 2.864 ? . 4_565 C(11) H(3) 3.338 ? . 3_655 C(11) H(9) 3.067 ? . 1_455 C(11) H(11) 3.444 ? . 1_455 C(12) H(1A) 2.75(2) ? . 2_565 C(13) H(1) 3.328 ? . 2_565 C(13) H(1A) 3.06(2) ? . 2_565 C(13) H(4) 3.128 ? . 2_465 C(13) H(5) 3.468 ? . 1_455 C(14) H(5) 3.148 ? . 1_455 H(1) O(2) 2.979 ? . 1_455 H(1) O(4) 3.432 ? . 2_465 H(1) C(4) 3.287 ? . 1_455 H(1) C(5) 3.153 ? . 1_455 H(1) C(6) 3.219 ? . 1_455 H(1) C(13) 3.328 ? . 2_465 H(1) H(4) 2.575 ? . 1_455 H(1) H(5) 2.562 ? . 1_455 H(1) H(6) 3.507 ? . 1_455 H(1) H(14) 2.375 ? . 2_465 H(1A) O(4) 2.09(2) ? . 2_465 H(1A) C(6) 3.57(2) ? . 2_465 H(1A) C(8) 3.44(2) ? . 4_664 H(1A) C(12) 2.75(2) ? . 2_465 H(1A) C(13) 3.06(2) ? . 2_465 H(1A) H(4) 3.206 ? . 2_465 H(1A) H(6) 2.756 ? . 2_465 H(1A) H(9) 3.056 ? . 4_664 H(1A) H(10) 2.875 ? . 4_664 H(1A) H(12) 3.520 ? . 2_465 H(1A) H(14) 2.493 ? . 2_465 H(1A) H(15) 3.019 ? . 2_565 H(2) O(2) 2.924 ? . 1_455 H(2) O(2) 3.266 ? . 2_455 H(2) C(3) 3.451 ? . 2_455 H(2) C(11) 2.864 ? . 4_564 H(2) H(3) 2.691 ? . 2_455 H(2) H(9) 3.238 ? . 4_664 H(2) H(10) 3.385 ? . 4_664 H(2) H(11) 2.995 ? . 4_664 H(2) H(17) 2.874 ? . 4_564 H(2) H(18) 2.658 ? . 4_564 H(2) H(19) 3.578 ? . 3_645 H(2) H(19) 2.579 ? . 4_564 H(3) O(2) 2.475 ? . 2_455 H(3) C(2) 3.301 ? . 2_555 H(3) C(4) 3.446 ? . 2_455 H(3) C(9) 3.556 ? . 4_664 H(3) C(11) 3.338 ? . 3_645 H(3) H(2) 2.691 ? . 2_555 H(3) H(3) 3.289 ? . 2_455 H(3) H(3) 3.289 ? . 2_555 H(3) H(11) 2.702 ? . 4_664 H(3) H(18) 3.437 ? . 3_645 H(3) H(19) 2.457 ? . 3_645 H(3) H(19) 2.862 ? . 4_664 H(4) O(1) 3.039 ? . 2_565 H(4) C(1) 3.575 ? . 1_655 H(4) C(13) 3.128 ? . 2_565 H(4) H(1) 2.575 ? . 1_655 H(4) H(1A) 3.206 ? . 2_565 H(4) H(14) 2.526 ? . 2_565 H(4) H(15) 3.558 ? . 1_655 H(4) H(15) 2.807 ? . 2_565 H(5) C(1) 3.227 ? . 1_655 H(5) C(13) 3.468 ? . 1_655 H(5) C(14) 3.148 ? . 1_655 H(5) H(1) 2.562 ? . 1_655 H(5) H(13) 3.564 ? . 3_745 H(5) H(15) 2.938 ? . 1_655 H(5) H(16) 2.505 ? . 1_655 H(6) O(1) 3.015 ? . 2_565 H(6) H(1) 3.507 ? . 1_655 H(6) H(1A) 2.756 ? . 2_565 H(6) H(15) 3.101 ? . 1_655 H(7) C(9) 3.220 ? . 3_745 H(7) H(11) 2.956 ? . 3_745 H(7) H(12) 2.600 ? . 3_745 H(7) H(13) 3.081 ? . 3_645 H(7) H(13) 3.541 ? . 3_745 H(7) H(18) 3.010 ? . 3_645 H(8) O(4) 3.446 ? . 3_645 H(8) C(10) 3.530 ? . 3_645 H(8) H(13) 2.672 ? . 3_645 H(9) O(4) 2.802 ? . 3_745 H(9) C(2) 3.596 ? . 4_665 H(9) C(11) 3.067 ? . 1_655 H(9) H(1A) 3.056 ? . 4_665 H(9) H(2) 3.238 ? . 4_665 H(9) H(17) 2.894 ? . 1_655 H(9) H(18) 2.389 ? . 1_655 H(10) O(1) 3.143 ? . 4_665 H(10) O(4) 3.555 ? . 3_645 H(10) O(4) 3.558 ? . 3_745 H(10) C(2) 3.324 ? . 4_665 H(10) C(3) 3.486 ? . 4_665 H(10) H(1A) 2.875 ? . 4_665 H(10) H(2) 3.385 ? . 4_665 H(10) H(18) 3.578 ? . 1_655 H(11) O(2) 2.611 ? . 3_755 H(11) C(2) 3.318 ? . 4_665 H(11) C(3) 3.176 ? . 4_665 H(11) C(4) 3.599 ? . 3_755 H(11) C(11) 3.444 ? . 1_655 H(11) H(2) 2.995 ? . 4_665 H(11) H(3) 2.702 ? . 4_665 H(11) H(7) 2.956 ? . 3_755 H(11) H(18) 2.498 ? . 1_655 H(12) C(7) 3.542 ? . 3_755 H(12) H(1A) 3.520 ? . 2_565 H(12) H(7) 2.600 ? . 3_755 H(12) H(18) 2.783 ? . 1_655 H(13) C(7) 3.337 ? . 3_655 H(13) H(5) 3.564 ? . 3_755 H(13) H(7) 3.081 ? . 3_655 H(13) H(7) 3.541 ? . 3_755 H(13) H(8) 2.672 ? . 3_655 H(13) H(16) 3.004 ? . 3_655 H(14) O(1) 2.770 ? . 2_565 H(14) C(1) 3.012 ? . 2_565 H(14) C(5) 3.519 ? . 2_465 H(14) H(1) 2.375 ? . 2_565 H(14) H(1A) 2.493 ? . 2_565 H(14) H(4) 2.526 ? . 2_465 H(14) H(15) 3.042 ? . 2_565 H(15) O(1) 2.621 ? . 2_465 H(15) C(6) 3.457 ? . 1_455 H(15) H(1A) 3.019 ? . 2_465 H(15) H(4) 3.558 ? . 1_455 H(15) H(4) 2.807 ? . 2_465 H(15) H(5) 2.938 ? . 1_455 H(15) H(6) 3.101 ? . 1_455 H(15) H(14) 3.042 ? . 2_465 H(16) C(6) 3.467 ? . 1_455 H(16) H(5) 2.505 ? . 1_455 H(16) H(13) 3.004 ? . 3_645 H(17) O(4) 2.783 ? . 3_645 H(17) H(2) 2.874 ? . 4_565 H(17) H(9) 2.894 ? . 1_455 H(18) O(2) 3.297 ? . 3_655 H(18) C(2) 3.509 ? . 4_565 H(18) C(4) 3.519 ? . 3_655 H(18) C(8) 3.073 ? . 1_455 H(18) C(9) 2.928 ? . 1_455 H(18) H(2) 2.658 ? . 4_565 H(18) H(3) 3.437 ? . 3_655 H(18) H(7) 3.010 ? . 3_655 H(18) H(9) 2.389 ? . 1_455 H(18) H(10) 3.578 ? . 1_455 H(18) H(11) 2.498 ? . 1_455 H(18) H(12) 2.783 ? . 1_455 H(19) O(2) 3.505 ? . 3_655 H(19) O(2) 3.177 ? . 4_665 H(19) C(2) 3.409 ? . 3_655 H(19) C(2) 3.526 ? . 4_565 H(19) C(3) 2.749 ? . 3_655 H(19) C(3) 3.255 ? . 4_665 H(19) C(4) 3.283 ? . 3_655 H(19) C(4) 3.458 ? . 4_665 H(19) H(2) 3.578 ? . 3_655 H(19) H(2) 2.579 ? . 4_565 H(19) H(3) 2.457 ? . 3_655 H(19) H(3) 2.862 ? . 4_665 #============================================================================== # 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 #==============================================================================