Supplementary Material (ESI) for Photochemical & Photobiological Sciences This journal is © The Royal Society of Chemistry and Owner Societies 2006 data_global _journal_name_full Photochem.Photobiol.Sci. _journal_coden_Cambridge 0171 _publ_contact_author_name 'Miguel A. Garcia-Garibay' _publ_contact_author_address ; Department of Chemistry University of California 405 Hilgard Avenue Los Angeles CA 90095-1569 UNITED STATES OF AMERICA ; _publ_contact_author_email MGG@CHEM.UCLA.EDU _publ_section_title ; Combination Vs Disproportionation in Dialkyl Biradicals. Selectivity Reversal in a Crystalline Solid ; loop_ _publ_author_name 'Miguel A. Garcia-Garibay' 'Tina Choe' 'Saeed I. Khan' data_1 _database_code_depnum_ccdc_archive 'CCDC 295161' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C23 H22 O5' _chemical_formula_sum 'C23 H22 O5' _chemical_formula_weight 378.41 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 12.4283(9) _cell_length_b 12.4686(8) _cell_length_c 12.8462(9) _cell_angle_alpha 85.951(2) _cell_angle_beta 88.9970(10) _cell_angle_gamma 78.8750(10) _cell_volume 1948.4(2) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 3321 _cell_measurement_theta_min 2.301 _cell_measurement_theta_max 23.8235 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.44 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.290 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 800 _exptl_absorpt_coefficient_mu 0.090 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9003 _exptl_absorpt_correction_T_max 0.9734 _exptl_absorpt_process_details Sadabs(Bruker) _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12879 _diffrn_reflns_av_R_equivalents 0.0167 _diffrn_reflns_av_sigmaI/netI 0.0421 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.59 _diffrn_reflns_theta_max 28.30 _reflns_number_total 8970 _reflns_number_gt 5214 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0513P)^2^+0.3187P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 8970 _refine_ls_number_parameters 509 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0907 _refine_ls_R_factor_gt 0.0444 _refine_ls_wR_factor_ref 0.1284 _refine_ls_wR_factor_gt 0.1033 _refine_ls_goodness_of_fit_ref 0.998 _refine_ls_restrained_S_all 0.998 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1A O 0.60285(11) 0.80302(11) 0.11702(10) 0.0591(4) Uani 1 1 d . . . O2A O 0.79849(11) 0.83039(11) 0.25641(14) 0.0755(5) Uani 1 1 d . . . O3A O 0.63810(11) 0.92200(10) 0.31073(11) 0.0595(4) Uani 1 1 d . . . O4A O 0.48637(16) 0.64458(13) -0.01264(11) 0.0874(5) Uani 1 1 d . . . O5A O 0.37789(11) 0.77584(12) 0.06814(10) 0.0643(4) Uani 1 1 d . . . C1A C 0.51327(14) 0.65649(14) 0.17147(13) 0.0428(4) Uani 1 1 d . . . C2A C 0.58711(13) 0.73887(13) 0.18811(13) 0.0409(4) Uani 1 1 d . . . C3A C 0.64935(13) 0.73275(13) 0.29076(13) 0.0422(4) Uani 1 1 d . . . C4A C 0.74195(15) 0.62866(14) 0.29393(16) 0.0511(4) Uani 1 1 d . . . H4A1 H 0.7766 0.6243 0.2257 0.061 Uiso 1 1 calc R . . H4A2 H 0.7970 0.6379 0.3434 0.061 Uiso 1 1 calc R . . C5A C 0.70680(15) 0.52146(14) 0.32303(14) 0.0482(4) Uani 1 1 d . . . C6A C 0.74739(18) 0.46111(16) 0.41353(16) 0.0627(5) Uani 1 1 d . . . H6A H 0.7966 0.4871 0.4543 0.075 Uiso 1 1 calc R . . C7A C 0.7161(2) 0.36323(19) 0.44417(19) 0.0767(7) Uani 1 1 d . . . H7A H 0.7437 0.3241 0.5054 0.092 Uiso 1 1 calc R . . C8A C 0.6440(2) 0.32371(18) 0.3838(2) 0.0777(7) Uani 1 1 d . . . H8A H 0.6226 0.2579 0.4041 0.093 Uiso 1 1 calc R . . C9A C 0.60393(18) 0.38209(16) 0.29342(18) 0.0654(6) Uani 1 1 d . . . H9A H 0.5557 0.3548 0.2526 0.078 Uiso 1 1 calc R . . C10A C 0.63393(15) 0.48120(14) 0.26164(15) 0.0496(4) Uani 1 1 d . . . C11A C 0.58805(16) 0.54153(14) 0.16192(15) 0.0536(5) Uani 1 1 d . . . H11A H 0.5461 0.4958 0.1283 0.064 Uiso 1 1 calc R . . H11B H 0.6490 0.5507 0.1161 0.064 Uiso 1 1 calc R . . C12A C 0.42391(14) 0.65410(14) 0.25770(14) 0.0472(4) Uani 1 1 d . . . H12A H 0.3607 0.6333 0.2273 0.057 Uiso 1 1 calc R . . H12B H 0.4524 0.5979 0.3117 0.057 Uiso 1 1 calc R . . C13A C 0.38662(14) 0.76107(14) 0.30779(14) 0.0458(4) Uani 1 1 d . . . C14A C 0.28078(16) 0.82256(18) 0.29322(16) 0.0624(5) Uani 1 1 d . . . H14A H 0.2321 0.7981 0.2506 0.075 Uiso 1 1 calc R . . C15A C 0.2474(2) 0.91926(19) 0.34131(19) 0.0761(7) Uani 1 1 d . . . H15A H 0.1772 0.9601 0.3299 0.091 Uiso 1 1 calc R . . C16A C 0.3179(2) 0.95487(18) 0.40586(19) 0.0739(7) Uani 1 1 d . . . H16A H 0.2951 1.0194 0.4390 0.089 Uiso 1 1 calc R . . C17A C 0.42252(18) 0.89501(15) 0.42157(15) 0.0598(5) Uani 1 1 d . . . H17A H 0.4696 0.9194 0.4659 0.072 Uiso 1 1 calc R . . C18A C 0.45877(15) 0.79872(14) 0.37210(13) 0.0450(4) Uani 1 1 d . . . C19A C 0.57343(14) 0.73385(14) 0.38871(13) 0.0468(4) Uani 1 1 d . . . H19A H 0.5690 0.6589 0.4111 0.056 Uiso 1 1 calc R . . H19B H 0.6069 0.7639 0.4448 0.056 Uiso 1 1 calc R . . C20A C 0.70591(16) 0.83195(15) 0.28321(15) 0.0497(4) Uani 1 1 d . . . C21A C 0.67949(19) 1.02298(16) 0.30146(19) 0.0699(6) Uani 1 1 d . . . H21A H 0.7367 1.0194 0.3516 0.105 Uiso 1 1 calc R . . H21B H 0.6211 1.0833 0.3142 0.105 Uiso 1 1 calc R . . H21C H 0.7082 1.0333 0.2324 0.105 Uiso 1 1 calc R . . C22A C 0.45946(16) 0.69078(16) 0.06462(14) 0.0513(5) Uani 1 1 d . . . C23A C 0.32566(19) 0.8175(2) -0.03026(17) 0.0789(7) Uani 1 1 d . . . H23A H 0.3780 0.8433 -0.0765 0.118 Uiso 1 1 calc R . . H23B H 0.2658 0.8767 -0.0185 0.118 Uiso 1 1 calc R . . H23C H 0.2985 0.7599 -0.0610 0.118 Uiso 1 1 calc R . . O1B O 0.25864(12) 0.22305(11) 0.36984(11) 0.0662(4) Uani 1 1 d . . . O2B O 0.44516(11) 0.21694(11) 0.21523(15) 0.0819(5) Uani 1 1 d . . . O3B O 0.33646(10) 0.11382(10) 0.15513(11) 0.0569(3) Uani 1 1 d . . . O4B O 0.07102(14) 0.35193(12) 0.51740(11) 0.0741(4) Uani 1 1 d . . . O5B O 0.03563(14) 0.20840(13) 0.44164(11) 0.0790(5) Uani 1 1 d . . . C1B C 0.09204(14) 0.34667(14) 0.33004(13) 0.0446(4) Uani 1 1 d . . . C2B C 0.20378(14) 0.27932(14) 0.30239(14) 0.0440(4) Uani 1 1 d . . . C3B C 0.25146(13) 0.29291(13) 0.19229(14) 0.0430(4) Uani 1 1 d . . . C4B C 0.28672(14) 0.40668(14) 0.17982(16) 0.0507(5) Uani 1 1 d . . . H4B1 H 0.3255 0.4161 0.2424 0.061 Uiso 1 1 calc R . . H4B2 H 0.3381 0.4058 0.1220 0.061 Uiso 1 1 calc R . . C5B C 0.19516(14) 0.50497(14) 0.16105(14) 0.0456(4) Uani 1 1 d . . . C6B C 0.19311(16) 0.57026(15) 0.06884(16) 0.0566(5) Uani 1 1 d . . . H6B H 0.2480 0.5520 0.0195 0.068 Uiso 1 1 calc R . . C7B C 0.11160(18) 0.66187(17) 0.04814(17) 0.0645(6) Uani 1 1 d . . . H7B H 0.1113 0.7036 -0.0148 0.077 Uiso 1 1 calc R . . C8B C 0.03114(17) 0.69053(17) 0.12147(18) 0.0630(5) Uani 1 1 d . . . H8B H -0.0236 0.7522 0.1088 0.076 Uiso 1 1 calc R . . C9B C 0.03234(15) 0.62728(15) 0.21336(16) 0.0547(5) Uani 1 1 d . . . H9B H -0.0218 0.6476 0.2630 0.066 Uiso 1 1 calc R . . C10B C 0.11202(14) 0.53354(14) 0.23471(14) 0.0466(4) Uani 1 1 d . . . C11B C 0.10685(16) 0.46771(14) 0.33659(14) 0.0518(5) Uani 1 1 d . . . H11C H 0.0465 0.5054 0.3772 0.062 Uiso 1 1 calc R . . H11D H 0.1738 0.4667 0.3747 0.062 Uiso 1 1 calc R . . C12B C -0.00136(14) 0.33599(15) 0.25461(14) 0.0506(4) Uani 1 1 d . . . H12C H -0.0704 0.3480 0.2924 0.061 Uiso 1 1 calc R . . H12D H -0.0060 0.3931 0.1987 0.061 Uiso 1 1 calc R . . C13B C 0.01355(14) 0.22656(15) 0.20742(14) 0.0479(4) Uani 1 1 d . . . C14B C -0.05452(16) 0.15212(18) 0.23422(17) 0.0638(6) Uani 1 1 d . . . H14B H -0.1112 0.1702 0.2819 0.077 Uiso 1 1 calc R . . C15B C -0.03904(19) 0.05201(19) 0.19111(19) 0.0727(6) Uani 1 1 d . . . H15B H -0.0845 0.0028 0.2103 0.087 Uiso 1 1 calc R . . C16B C 0.04384(19) 0.02512(18) 0.11963(18) 0.0690(6) Uani 1 1 d . . . H16B H 0.0547 -0.0424 0.0907 0.083 Uiso 1 1 calc R . . C17B C 0.11077(17) 0.09850(16) 0.09104(16) 0.0575(5) Uani 1 1 d . . . H17B H 0.1658 0.0804 0.0418 0.069 Uiso 1 1 calc R . . C18B C 0.09729(14) 0.19917(15) 0.13473(14) 0.0459(4) Uani 1 1 d . . . C19B C 0.17108(14) 0.27934(15) 0.10495(14) 0.0471(4) Uani 1 1 d . . . H19C H 0.1258 0.3503 0.0859 0.057 Uiso 1 1 calc R . . H19D H 0.2134 0.2553 0.0438 0.057 Uiso 1 1 calc R . . C20B C 0.35642(15) 0.20511(14) 0.18964(15) 0.0498(4) Uani 1 1 d . . . C21B C 0.42796(17) 0.02383(16) 0.14783(19) 0.0671(6) Uani 1 1 d . . . H21D H 0.4798 0.0441 0.0975 0.101 Uiso 1 1 calc R . . H21E H 0.4023 -0.0390 0.1264 0.101 Uiso 1 1 calc R . . H21F H 0.4627 0.0065 0.2147 0.101 Uiso 1 1 calc R . . C22B C 0.06606(15) 0.30431(16) 0.44049(15) 0.0524(5) Uani 1 1 d . . . C23B C 0.0107(3) 0.1603(2) 0.54187(19) 0.0985(9) Uani 1 1 d . . . H23D H 0.0743 0.1486 0.5856 0.148 Uiso 1 1 calc R . . H23E H -0.0107 0.0914 0.5333 0.148 Uiso 1 1 calc R . . H23F H -0.0483 0.2086 0.5737 0.148 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 O1A 0.0676(9) 0.0615(8) 0.0526(8) 0.0064(7) 0.0014(7) -0.0269(7) O2A 0.0477(8) 0.0615(9) 0.1220(13) -0.0081(9) 0.0132(8) -0.0229(7) O3A 0.0589(8) 0.0436(7) 0.0817(10) -0.0118(7) 0.0079(7) -0.0218(6) O4A 0.1293(14) 0.0811(11) 0.0469(9) -0.0223(8) -0.0122(9) 0.0000(10) O5A 0.0608(8) 0.0759(10) 0.0511(8) -0.0016(7) -0.0067(7) -0.0007(7) C1A 0.0484(10) 0.0441(10) 0.0388(9) -0.0097(7) 0.0000(8) -0.0142(8) C2A 0.0401(9) 0.0384(9) 0.0444(10) -0.0073(8) 0.0060(8) -0.0073(7) C3A 0.0416(9) 0.0414(9) 0.0466(10) -0.0066(8) 0.0000(8) -0.0142(7) C4A 0.0432(10) 0.0504(11) 0.0610(12) -0.0054(9) -0.0033(9) -0.0116(8) C5A 0.0486(10) 0.0419(10) 0.0530(11) -0.0069(8) 0.0017(9) -0.0046(8) C6A 0.0712(14) 0.0530(12) 0.0606(13) -0.0048(10) -0.0051(11) -0.0033(10) C7A 0.0996(18) 0.0587(14) 0.0645(15) 0.0079(11) 0.0022(13) -0.0011(13) C8A 0.0988(18) 0.0441(12) 0.0891(18) 0.0024(12) 0.0139(15) -0.0152(12) C9A 0.0753(14) 0.0432(11) 0.0805(16) -0.0108(11) 0.0023(12) -0.0161(10) C10A 0.0551(11) 0.0394(10) 0.0540(11) -0.0105(8) 0.0036(9) -0.0063(8) C11A 0.0634(12) 0.0455(10) 0.0545(12) -0.0172(9) -0.0006(9) -0.0120(9) C12A 0.0496(10) 0.0490(10) 0.0478(10) -0.0050(8) 0.0006(8) -0.0211(8) C13A 0.0447(10) 0.0490(10) 0.0449(10) -0.0009(8) 0.0114(8) -0.0137(8) C14A 0.0497(11) 0.0749(14) 0.0612(13) 0.0032(11) 0.0131(10) -0.0124(10) C15A 0.0655(14) 0.0721(15) 0.0778(16) 0.0094(13) 0.0308(13) 0.0106(12) C16A 0.0937(18) 0.0523(13) 0.0695(15) -0.0056(11) 0.0337(14) -0.0013(12) C17A 0.0770(14) 0.0495(11) 0.0544(12) -0.0125(9) 0.0204(10) -0.0148(10) C18A 0.0538(10) 0.0438(10) 0.0400(9) -0.0066(8) 0.0119(8) -0.0153(8) C19A 0.0561(11) 0.0472(10) 0.0411(10) -0.0079(8) 0.0012(8) -0.0183(9) C20A 0.0496(11) 0.0478(11) 0.0552(11) -0.0052(9) -0.0032(9) -0.0176(9) C21A 0.0792(15) 0.0482(12) 0.0899(16) -0.0080(11) -0.0031(13) -0.0295(11) C22A 0.0613(12) 0.0523(11) 0.0447(11) -0.0090(9) -0.0018(9) -0.0198(10) C23A 0.0716(15) 0.0982(18) 0.0639(14) 0.0187(13) -0.0192(12) -0.0161(13) O1B 0.0683(9) 0.0628(9) 0.0604(9) 0.0012(7) -0.0098(7) 0.0041(7) O2B 0.0413(8) 0.0548(9) 0.1514(16) -0.0187(9) -0.0121(9) -0.0086(7) O3B 0.0471(7) 0.0435(7) 0.0800(9) -0.0168(7) 0.0000(7) -0.0040(6) O4B 0.1119(13) 0.0683(9) 0.0447(8) -0.0125(7) 0.0082(8) -0.0217(9) O5B 0.1175(13) 0.0790(10) 0.0543(9) -0.0003(8) 0.0026(9) -0.0548(10) C1B 0.0461(10) 0.0462(10) 0.0432(10) -0.0096(8) 0.0026(8) -0.0107(8) C2B 0.0465(10) 0.0379(9) 0.0496(10) -0.0083(8) -0.0056(8) -0.0108(8) C3B 0.0373(9) 0.0400(9) 0.0527(10) -0.0087(8) 0.0018(8) -0.0082(7) C4B 0.0429(10) 0.0438(10) 0.0667(12) -0.0073(9) 0.0062(9) -0.0106(8) C5B 0.0442(10) 0.0398(9) 0.0549(11) -0.0061(8) 0.0031(8) -0.0127(8) C6B 0.0584(12) 0.0520(11) 0.0609(12) -0.0063(10) 0.0106(10) -0.0144(10) C7B 0.0684(14) 0.0596(13) 0.0653(14) 0.0085(10) -0.0039(11) -0.0161(11) C8B 0.0523(12) 0.0511(12) 0.0824(15) 0.0028(11) -0.0065(11) -0.0042(9) C9B 0.0468(10) 0.0467(11) 0.0698(13) -0.0069(10) 0.0041(9) -0.0062(8) C10B 0.0465(10) 0.0423(10) 0.0526(11) -0.0088(8) 0.0011(8) -0.0105(8) C11B 0.0580(11) 0.0460(10) 0.0511(11) -0.0121(9) 0.0047(9) -0.0069(9) C12B 0.0419(10) 0.0596(12) 0.0503(11) -0.0081(9) 0.0031(8) -0.0083(8) C13B 0.0423(9) 0.0572(11) 0.0464(10) -0.0058(8) -0.0059(8) -0.0137(8) C14B 0.0516(12) 0.0831(15) 0.0637(13) -0.0083(11) -0.0013(10) -0.0293(11) C15B 0.0729(15) 0.0769(16) 0.0795(16) -0.0060(13) -0.0123(13) -0.0407(13) C16B 0.0772(15) 0.0620(13) 0.0753(15) -0.0174(11) -0.0154(12) -0.0262(12) C17B 0.0601(12) 0.0600(12) 0.0560(12) -0.0152(10) -0.0061(10) -0.0163(10) C18B 0.0455(10) 0.0511(10) 0.0436(10) -0.0068(8) -0.0059(8) -0.0135(8) C19B 0.0455(10) 0.0492(10) 0.0469(10) -0.0087(8) 0.0022(8) -0.0079(8) C20B 0.0426(10) 0.0424(10) 0.0651(12) -0.0075(9) 0.0038(9) -0.0090(8) C21B 0.0600(12) 0.0462(11) 0.0913(16) -0.0141(11) 0.0125(12) 0.0012(9) C22B 0.0544(11) 0.0548(12) 0.0492(11) -0.0054(9) 0.0019(9) -0.0125(9) C23B 0.135(2) 0.106(2) 0.0679(16) 0.0186(14) 0.0034(16) -0.0651(19) _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 O1A C2A 1.210(2) . ? O2A C20A 1.192(2) . ? O3A C20A 1.333(2) . ? O3A C21A 1.446(2) . ? O4A C22A 1.193(2) . ? O5A C22A 1.321(2) . ? O5A C23A 1.447(2) . ? C1A C2A 1.531(2) . ? C1A C22A 1.534(2) . ? C1A C12A 1.558(2) . ? C1A C11A 1.562(2) . ? C2A C3A 1.530(2) . ? C3A C20A 1.533(2) . ? C3A C4A 1.558(2) . ? C3A C19A 1.559(2) . ? C4A C5A 1.505(2) . ? C4A H4A1 0.9700 . ? C4A H4A2 0.9700 . ? C5A C6A 1.387(3) . ? C5A C10A 1.397(2) . ? C6A C7A 1.380(3) . ? C6A H6A 0.9300 . ? C7A C8A 1.377(3) . ? C7A H7A 0.9300 . ? C8A C9A 1.374(3) . ? C8A H8A 0.9300 . ? C9A C10A 1.391(3) . ? C9A H9A 0.9300 . ? C10A C11A 1.502(3) . ? C11A H11A 0.9700 . ? C11A H11B 0.9700 . ? C12A C13A 1.510(2) . ? C12A H12A 0.9700 . ? C12A H12B 0.9700 . ? C13A C18A 1.396(2) . ? C13A C14A 1.397(3) . ? C14A C15A 1.382(3) . ? C14A H14A 0.9300 . ? C15A C16A 1.371(3) . ? C15A H15A 0.9300 . ? C16A C17A 1.379(3) . ? C16A H16A 0.9300 . ? C17A C18A 1.392(2) . ? C17A H17A 0.9300 . ? C18A C19A 1.507(2) . ? C19A H19A 0.9700 . ? C19A H19B 0.9700 . ? C21A H21A 0.9600 . ? C21A H21B 0.9600 . ? C21A H21C 0.9600 . ? C23A H23A 0.9600 . ? C23A H23B 0.9600 . ? C23A H23C 0.9600 . ? O1B C2B 1.207(2) . ? O2B C20B 1.195(2) . ? O3B C20B 1.318(2) . ? O3B C21B 1.442(2) . ? O4B C22B 1.197(2) . ? O5B C22B 1.321(2) . ? O5B C23B 1.436(3) . ? C1B C2B 1.528(2) . ? C1B C22B 1.530(3) . ? C1B C12B 1.556(2) . ? C1B C11B 1.563(2) . ? C2B C3B 1.535(2) . ? C3B C20B 1.534(2) . ? C3B C19B 1.554(2) . ? C3B C4B 1.561(2) . ? C4B C5B 1.512(2) . ? C4B H4B1 0.9700 . ? C4B H4B2 0.9700 . ? C5B C6B 1.387(3) . ? C5B C10B 1.400(2) . ? C6B C7B 1.386(3) . ? C6B H6B 0.9300 . ? C7B C8B 1.375(3) . ? C7B H7B 0.9300 . ? C8B C9B 1.371(3) . ? C8B H8B 0.9300 . ? C9B C10B 1.393(2) . ? C9B H9B 0.9300 . ? C10B C11B 1.502(3) . ? C11B H11C 0.9700 . ? C11B H11D 0.9700 . ? C12B C13B 1.510(2) . ? C12B H12C 0.9700 . ? C12B H12D 0.9700 . ? C13B C14B 1.394(3) . ? C13B C18B 1.395(2) . ? C14B C15B 1.379(3) . ? C14B H14B 0.9300 . ? C15B C16B 1.376(3) . ? C15B H15B 0.9300 . ? C16B C17B 1.378(3) . ? C16B H16B 0.9300 . ? C17B C18B 1.391(2) . ? C17B H17B 0.9300 . ? C18B C19B 1.508(2) . ? C19B H19C 0.9700 . ? C19B H19D 0.9700 . ? C21B H21D 0.9600 . ? C21B H21E 0.9600 . ? C21B H21F 0.9600 . ? C23B H23D 0.9600 . ? C23B H23E 0.9600 . ? C23B H23F 0.9600 . ? 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 C20A O3A C21A 116.89(15) . . ? C22A O5A C23A 116.25(16) . . ? C2A C1A C22A 105.87(14) . . ? C2A C1A C12A 113.33(13) . . ? C22A C1A C12A 110.28(14) . . ? C2A C1A C11A 108.13(14) . . ? C22A C1A C11A 106.74(14) . . ? C12A C1A C11A 112.09(14) . . ? O1A C2A C3A 120.02(15) . . ? O1A C2A C1A 119.72(16) . . ? C3A C2A C1A 120.00(15) . . ? C2A C3A C20A 105.48(14) . . ? C2A C3A C4A 108.04(13) . . ? C20A C3A C4A 106.80(14) . . ? C2A C3A C19A 113.06(13) . . ? C20A C3A C19A 111.22(14) . . ? C4A C3A C19A 111.84(14) . . ? C5A C4A C3A 116.01(14) . . ? C5A C4A H4A1 108.3 . . ? C3A C4A H4A1 108.3 . . ? C5A C4A H4A2 108.3 . . ? C3A C4A H4A2 108.3 . . ? H4A1 C4A H4A2 107.4 . . ? C6A C5A C10A 118.97(18) . . ? C6A C5A C4A 119.19(17) . . ? C10A C5A C4A 121.84(17) . . ? C7A C6A C5A 121.2(2) . . ? C7A C6A H6A 119.4 . . ? C5A C6A H6A 119.4 . . ? C8A C7A C6A 119.8(2) . . ? C8A C7A H7A 120.1 . . ? C6A C7A H7A 120.1 . . ? C9A C8A C7A 119.6(2) . . ? C9A C8A H8A 120.2 . . ? C7A C8A H8A 120.2 . . ? C8A C9A C10A 121.4(2) . . ? C8A C9A H9A 119.3 . . ? C10A C9A H9A 119.3 . . ? C9A C10A C5A 118.98(19) . . ? C9A C10A C11A 119.24(18) . . ? C5A C10A C11A 121.77(16) . . ? C10A C11A C1A 116.72(14) . . ? C10A C11A H11A 108.1 . . ? C1A C11A H11A 108.1 . . ? C10A C11A H11B 108.1 . . ? C1A C11A H11B 108.1 . . ? H11A C11A H11B 107.3 . . ? C13A C12A C1A 114.79(14) . . ? C13A C12A H12A 108.6 . . ? C1A C12A H12A 108.6 . . ? C13A C12A H12B 108.6 . . ? C1A C12A H12B 108.6 . . ? H12A C12A H12B 107.5 . . ? C18A C13A C14A 118.94(17) . . ? C18A C13A C12A 119.35(16) . . ? C14A C13A C12A 121.70(17) . . ? C15A C14A C13A 120.9(2) . . ? C15A C14A H14A 119.6 . . ? C13A C14A H14A 119.6 . . ? C16A C15A C14A 120.0(2) . . ? C16A C15A H15A 120.0 . . ? C14A C15A H15A 120.0 . . ? C15A C16A C17A 120.0(2) . . ? C15A C16A H16A 120.0 . . ? C17A C16A H16A 120.0 . . ? C16A C17A C18A 121.1(2) . . ? C16A C17A H17A 119.5 . . ? C18A C17A H17A 119.5 . . ? C17A C18A C13A 119.13(18) . . ? C17A C18A C19A 121.01(17) . . ? C13A C18A C19A 119.84(15) . . ? C18A C19A C3A 114.65(14) . . ? C18A C19A H19A 108.6 . . ? C3A C19A H19A 108.6 . . ? C18A C19A H19B 108.6 . . ? C3A C19A H19B 108.6 . . ? H19A C19A H19B 107.6 . . ? O2A C20A O3A 123.48(17) . . ? O2A C20A C3A 125.22(17) . . ? O3A C20A C3A 111.30(15) . . ? O3A C21A H21A 109.5 . . ? O3A C21A H21B 109.5 . . ? H21A C21A H21B 109.5 . . ? O3A C21A H21C 109.5 . . ? H21A C21A H21C 109.5 . . ? H21B C21A H21C 109.5 . . ? O4A C22A O5A 123.59(19) . . ? O4A C22A C1A 124.01(18) . . ? O5A C22A C1A 112.38(15) . . ? O5A C23A H23A 109.5 . . ? O5A C23A H23B 109.5 . . ? H23A C23A H23B 109.5 . . ? O5A C23A H23C 109.5 . . ? H23A C23A H23C 109.5 . . ? H23B C23A H23C 109.5 . . ? C20B O3B C21B 117.40(15) . . ? C22B O5B C23B 116.66(17) . . ? C2B C1B C22B 105.70(15) . . ? C2B C1B C12B 113.80(13) . . ? C22B C1B C12B 109.73(14) . . ? C2B C1B C11B 107.27(14) . . ? C22B C1B C11B 106.96(14) . . ? C12B C1B C11B 112.93(15) . . ? O1B C2B C1B 119.66(16) . . ? O1B C2B C3B 119.96(16) . . ? C1B C2B C3B 120.03(15) . . ? C20B C3B C2B 105.50(14) . . ? C20B C3B C19B 110.86(14) . . ? C2B C3B C19B 112.97(13) . . ? C20B C3B C4B 107.15(13) . . ? C2B C3B C4B 108.17(14) . . ? C19B C3B C4B 111.83(15) . . ? C5B C4B C3B 115.99(14) . . ? C5B C4B H4B1 108.3 . . ? C3B C4B H4B1 108.3 . . ? C5B C4B H4B2 108.3 . . ? C3B C4B H4B2 108.3 . . ? H4B1 C4B H4B2 107.4 . . ? C6B C5B C10B 118.37(17) . . ? C6B C5B C4B 119.58(16) . . ? C10B C5B C4B 122.05(16) . . ? C7B C6B C5B 121.91(18) . . ? C7B C6B H6B 119.0 . . ? C5B C6B H6B 119.0 . . ? C8B C7B C6B 119.5(2) . . ? C8B C7B H7B 120.3 . . ? C6B C7B H7B 120.3 . . ? C9B C8B C7B 119.39(19) . . ? C9B C8B H8B 120.3 . . ? C7B C8B H8B 120.3 . . ? C8B C9B C10B 122.07(18) . . ? C8B C9B H9B 119.0 . . ? C10B C9B H9B 119.0 . . ? C9B C10B C5B 118.78(17) . . ? C9B C10B C11B 118.89(16) . . ? C5B C10B C11B 122.33(16) . . ? C10B C11B C1B 116.54(14) . . ? C10B C11B H11C 108.2 . . ? C1B C11B H11C 108.2 . . ? C10B C11B H11D 108.2 . . ? C1B C11B H11D 108.2 . . ? H11C C11B H11D 107.3 . . ? C13B C12B C1B 114.20(15) . . ? C13B C12B H12C 108.7 . . ? C1B C12B H12C 108.7 . . ? C13B C12B H12D 108.7 . . ? C1B C12B H12D 108.7 . . ? H12C C12B H12D 107.6 . . ? C14B C13B C18B 118.99(17) . . ? C14B C13B C12B 121.75(17) . . ? C18B C13B C12B 119.26(16) . . ? C15B C14B C13B 121.0(2) . . ? C15B C14B H14B 119.5 . . ? C13B C14B H14B 119.5 . . ? C16B C15B C14B 119.9(2) . . ? C16B C15B H15B 120.1 . . ? C14B C15B H15B 120.1 . . ? C15B C16B C17B 119.9(2) . . ? C15B C16B H16B 120.1 . . ? C17B C16B H16B 120.1 . . ? C16B C17B C18B 121.02(19) . . ? C16B C17B H17B 119.5 . . ? C18B C17B H17B 119.5 . . ? C17B C18B C13B 119.24(17) . . ? C17B C18B C19B 121.38(16) . . ? C13B C18B C19B 119.38(15) . . ? C18B C19B C3B 114.29(15) . . ? C18B C19B H19C 108.7 . . ? C3B C19B H19C 108.7 . . ? C18B C19B H19D 108.7 . . ? C3B C19B H19D 108.7 . . ? H19C C19B H19D 107.6 . . ? O2B C20B O3B 123.85(17) . . ? O2B C20B C3B 124.98(16) . . ? O3B C20B C3B 111.17(15) . . ? O3B C21B H21D 109.5 . . ? O3B C21B H21E 109.5 . . ? H21D C21B H21E 109.5 . . ? O3B C21B H21F 109.5 . . ? H21D C21B H21F 109.5 . . ? H21E C21B H21F 109.5 . . ? O4B C22B O5B 123.21(18) . . ? O4B C22B C1B 124.76(17) . . ? O5B C22B C1B 112.03(16) . . ? O5B C23B H23D 109.5 . . ? O5B C23B H23E 109.5 . . ? H23D C23B H23E 109.5 . . ? O5B C23B H23F 109.5 . . ? H23D C23B H23F 109.5 . . ? H23E C23B H23F 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C22A C1A C2A O1A -9.2(2) . . . . ? C12A C1A C2A O1A -130.18(17) . . . . ? C11A C1A C2A O1A 104.92(18) . . . . ? C22A C1A C2A C3A 176.69(14) . . . . ? C12A C1A C2A C3A 55.7(2) . . . . ? C11A C1A C2A C3A -69.22(18) . . . . ? O1A C2A C3A C20A 10.5(2) . . . . ? C1A C2A C3A C20A -175.42(14) . . . . ? O1A C2A C3A C4A -103.48(17) . . . . ? C1A C2A C3A C4A 70.65(18) . . . . ? O1A C2A C3A C19A 132.20(16) . . . . ? C1A C2A C3A C19A -53.68(19) . . . . ? C2A C3A C4A C5A -78.86(19) . . . . ? C20A C3A C4A C5A 168.09(15) . . . . ? C19A C3A C4A C5A 46.2(2) . . . . ? C3A C4A C5A C6A -116.78(19) . . . . ? C3A C4A C5A C10A 62.9(2) . . . . ? C10A C5A C6A C7A -0.7(3) . . . . ? C4A C5A C6A C7A 178.98(18) . . . . ? C5A C6A C7A C8A 0.5(3) . . . . ? C6A C7A C8A C9A 0.1(3) . . . . ? C7A C8A C9A C10A -0.5(3) . . . . ? C8A C9A C10A C5A 0.3(3) . . . . ? C8A C9A C10A C11A 179.76(19) . . . . ? C6A C5A C10A C9A 0.3(3) . . . . ? C4A C5A C10A C9A -179.39(17) . . . . ? C6A C5A C10A C11A -179.14(17) . . . . ? C4A C5A C10A C11A 1.2(3) . . . . ? C9A C10A C11A C1A 116.52(19) . . . . ? C5A C10A C11A C1A -64.1(2) . . . . ? C2A C1A C11A C10A 77.3(2) . . . . ? C22A C1A C11A C10A -169.22(16) . . . . ? C12A C1A C11A C10A -48.4(2) . . . . ? C2A C1A C12A C13A 29.0(2) . . . . ? C22A C1A C12A C13A -89.51(18) . . . . ? C11A C1A C12A C13A 151.72(15) . . . . ? C1A C12A C13A C18A -69.2(2) . . . . ? C1A C12A C13A C14A 112.12(19) . . . . ? C18A C13A C14A C15A 0.1(3) . . . . ? C12A C13A C14A C15A 178.76(17) . . . . ? C13A C14A C15A C16A -1.2(3) . . . . ? C14A C15A C16A C17A 0.9(3) . . . . ? C15A C16A C17A C18A 0.5(3) . . . . ? C16A C17A C18A C13A -1.7(3) . . . . ? C16A C17A C18A C19A 179.53(17) . . . . ? C14A C13A C18A C17A 1.4(2) . . . . ? C12A C13A C18A C17A -177.34(16) . . . . ? C14A C13A C18A C19A -179.84(16) . . . . ? C12A C13A C18A C19A 1.4(2) . . . . ? C17A C18A C19A C3A -112.32(18) . . . . ? C13A C18A C19A C3A 68.9(2) . . . . ? C2A C3A C19A C18A -31.78(19) . . . . ? C20A C3A C19A C18A 86.68(18) . . . . ? C4A C3A C19A C18A -154.00(14) . . . . ? C21A O3A C20A O2A 3.4(3) . . . . ? C21A O3A C20A C3A -176.64(16) . . . . ? C2A C3A C20A O2A -96.3(2) . . . . ? C4A C3A C20A O2A 18.4(3) . . . . ? C19A C3A C20A O2A 140.7(2) . . . . ? C2A C3A C20A O3A 83.70(17) . . . . ? C4A C3A C20A O3A -161.51(15) . . . . ? C19A C3A C20A O3A -39.2(2) . . . . ? C23A O5A C22A O4A -4.5(3) . . . . ? C23A O5A C22A C1A 177.03(16) . . . . ? C2A C1A C22A O4A 103.8(2) . . . . ? C12A C1A C22A O4A -133.2(2) . . . . ? C11A C1A C22A O4A -11.2(3) . . . . ? C2A C1A C22A O5A -77.73(18) . . . . ? C12A C1A C22A O5A 45.24(19) . . . . ? C11A C1A C22A O5A 167.23(15) . . . . ? C22B C1B C2B O1B -12.2(2) . . . . ? C12B C1B C2B O1B -132.64(18) . . . . ? C11B C1B C2B O1B 101.70(19) . . . . ? C22B C1B C2B C3B 174.56(14) . . . . ? C12B C1B C2B C3B 54.1(2) . . . . ? C11B C1B C2B C3B -71.57(18) . . . . ? O1B C2B C3B C20B 12.7(2) . . . . ? C1B C2B C3B C20B -174.07(14) . . . . ? O1B C2B C3B C19B 133.94(17) . . . . ? C1B C2B C3B C19B -52.81(19) . . . . ? O1B C2B C3B C4B -101.72(18) . . . . ? C1B C2B C3B C4B 71.53(18) . . . . ? C20B C3B C4B C5B 169.51(16) . . . . ? C2B C3B C4B C5B -77.19(19) . . . . ? C19B C3B C4B C5B 47.8(2) . . . . ? C3B C4B C5B C6B -117.84(19) . . . . ? C3B C4B C5B C10B 62.9(2) . . . . ? C10B C5B C6B C7B -0.1(3) . . . . ? C4B C5B C6B C7B -179.40(17) . . . . ? C5B C6B C7B C8B 1.1(3) . . . . ? C6B C7B C8B C9B -0.7(3) . . . . ? C7B C8B C9B C10B -0.8(3) . . . . ? C8B C9B C10B C5B 1.8(3) . . . . ? C8B C9B C10B C11B -179.17(18) . . . . ? C6B C5B C10B C9B -1.3(3) . . . . ? C4B C5B C10B C9B 177.94(16) . . . . ? C6B C5B C10B C11B 179.69(17) . . . . ? C4B C5B C10B C11B -1.0(3) . . . . ? C9B C10B C11B C1B 118.63(18) . . . . ? C5B C10B C11B C1B -62.4(2) . . . . ? C2B C1B C11B C10B 78.13(19) . . . . ? C22B C1B C11B C10B -168.86(15) . . . . ? C12B C1B C11B C10B -48.1(2) . . . . ? C2B C1B C12B C13B 30.5(2) . . . . ? C22B C1B C12B C13B -87.68(18) . . . . ? C11B C1B C12B C13B 153.10(15) . . . . ? C1B C12B C13B C14B 110.9(2) . . . . ? C1B C12B C13B C18B -69.3(2) . . . . ? C18B C13B C14B C15B 0.9(3) . . . . ? C12B C13B C14B C15B -179.35(19) . . . . ? C13B C14B C15B C16B -0.8(3) . . . . ? C14B C15B C16B C17B -0.3(3) . . . . ? C15B C16B C17B C18B 1.2(3) . . . . ? C16B C17B C18B C13B -1.0(3) . . . . ? C16B C17B C18B C19B 179.19(18) . . . . ? C14B C13B C18B C17B -0.1(3) . . . . ? C12B C13B C18B C17B -179.79(17) . . . . ? C14B C13B C18B C19B 179.77(17) . . . . ? C12B C13B C18B C19B 0.0(3) . . . . ? C17B C18B C19B C3B -109.47(19) . . . . ? C13B C18B C19B C3B 70.7(2) . . . . ? C20B C3B C19B C18B 85.69(18) . . . . ? C2B C3B C19B C18B -32.5(2) . . . . ? C4B C3B C19B C18B -154.80(15) . . . . ? C21B O3B C20B O2B -0.3(3) . . . . ? C21B O3B C20B C3B 179.67(16) . . . . ? C2B C3B C20B O2B -88.1(2) . . . . ? C19B C3B C20B O2B 149.3(2) . . . . ? C4B C3B C20B O2B 27.1(3) . . . . ? C2B C3B C20B O3B 92.01(17) . . . . ? C19B C3B C20B O3B -30.6(2) . . . . ? C4B C3B C20B O3B -152.89(15) . . . . ? C23B O5B C22B O4B -1.6(3) . . . . ? C23B O5B C22B C1B 179.18(19) . . . . ? C2B C1B C22B O4B 105.3(2) . . . . ? C12B C1B C22B O4B -131.6(2) . . . . ? C11B C1B C22B O4B -8.7(3) . . . . ? C2B C1B C22B O5B -75.49(19) . . . . ? C12B C1B C22B O5B 47.6(2) . . . . ? C11B C1B C22B O5B 170.43(16) . . . . ? _diffrn_measured_fraction_theta_max 0.926 _diffrn_reflns_theta_full 24.50 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.179 _refine_diff_density_min -0.165 _refine_diff_density_rms 0.036 #====END # # #gg903sm # # data_(Z)-2 _database_code_depnum_ccdc_archive 'CCDC 295162' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C22 H22 O4' _chemical_formula_sum 'C22 H22 O4' _chemical_formula_weight 350.40 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'C 2/c' _symmetry_space_group_name_Hall '-C 2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 25.049(3) _cell_length_b 11.3809(12) _cell_length_c 14.7771(15) _cell_angle_alpha 90.00 _cell_angle_beta 117.603(2) _cell_angle_gamma 90.00 _cell_volume 3733.2(7) _cell_formula_units_Z 8 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 5564 _cell_measurement_theta_min 2.27 _cell_measurement_theta_max 26.99 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.46 _exptl_crystal_size_min 0.40 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.247 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1488 _exptl_absorpt_coefficient_mu 0.085 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9130 _exptl_absorpt_correction_T_max 0.9668 _exptl_absorpt_process_details 'Sadabs (Bruker)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16369 _diffrn_reflns_av_R_equivalents 0.0209 _diffrn_reflns_av_sigmaI/netI 0.0222 _diffrn_reflns_limit_h_min -33 _diffrn_reflns_limit_h_max 33 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.83 _diffrn_reflns_theta_max 28.31 _reflns_number_total 4536 _reflns_number_gt 2885 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0774P)^2^+1.3792P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4536 _refine_ls_number_parameters 237 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0817 _refine_ls_R_factor_gt 0.0493 _refine_ls_wR_factor_ref 0.1607 _refine_ls_wR_factor_gt 0.1376 _refine_ls_goodness_of_fit_ref 1.033 _refine_ls_restrained_S_all 1.033 _refine_ls_shift/su_max 0.007 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.08404(8) 0.23096(14) -0.05574(10) 0.0916(5) Uani 1 1 d . . . O2 O 0.04963(6) 0.38747(12) -0.01054(9) 0.0721(4) Uani 1 1 d . . . O3 O 0.08531(7) 0.37876(15) 0.29932(13) 0.0919(5) Uani 1 1 d . . . O4 O 0.10735(7) 0.24212(13) 0.41821(10) 0.0768(4) Uani 1 1 d . . . C1 C 0.13544(7) 0.29859(15) 0.11887(11) 0.0516(4) Uani 1 1 d . . . H1 H 0.1154 0.3153 0.1608 0.062 Uiso 1 1 calc R . . C2 C 0.16638(8) 0.17759(16) 0.15178(13) 0.0589(4) Uani 1 1 d . . . H2A H 0.1709 0.1442 0.0953 0.071 Uiso 1 1 calc R . . H2B H 0.2064 0.1890 0.2079 0.071 Uiso 1 1 calc R . . C3 C 0.13325(8) 0.09047(15) 0.18451(13) 0.0549(4) Uani 1 1 d . . . C4 C 0.14629(8) 0.07504(15) 0.28731(13) 0.0569(4) Uani 1 1 d . . . C5 C 0.19439(9) 0.14572(17) 0.37408(13) 0.0631(5) Uani 1 1 d . . . H5A H 0.1979 0.1181 0.4387 0.076 Uiso 1 1 calc R . . H5B H 0.2330 0.1342 0.3748 0.076 Uiso 1 1 calc R . . C6 C 0.17880(8) 0.27512(16) 0.36184(12) 0.0547(4) Uani 1 1 d . . . C7 C 0.21182(8) 0.35368(16) 0.34354(12) 0.0561(4) Uani 1 1 d . . . H7 H 0.2498 0.3288 0.3551 0.067 Uiso 1 1 calc R . . C8 C 0.19556(7) 0.47595(16) 0.30701(13) 0.0559(4) Uani 1 1 d . . . C9 C 0.18047(7) 0.49833(15) 0.20459(13) 0.0539(4) Uani 1 1 d . . . C10 C 0.18075(8) 0.40098(17) 0.13554(13) 0.0607(5) Uani 1 1 d . . . H10A H 0.2211 0.3684 0.1640 0.073 Uiso 1 1 calc R . . H10B H 0.1716 0.4345 0.0696 0.073 Uiso 1 1 calc R . . C11 C 0.08745(9) 0.02250(17) 0.11102(15) 0.0663(5) Uani 1 1 d . . . H11 H 0.0784 0.0312 0.0428 0.080 Uiso 1 1 calc R . . C12 C 0.05518(10) -0.05726(18) 0.13651(18) 0.0756(6) Uani 1 1 d . . . H12 H 0.0243 -0.1005 0.0857 0.091 Uiso 1 1 calc R . . C13 C 0.06863(10) -0.07269(18) 0.23646(19) 0.0761(6) Uani 1 1 d . . . H13 H 0.0474 -0.1271 0.2542 0.091 Uiso 1 1 calc R . . C14 C 0.11366(10) -0.00743(17) 0.31046(17) 0.0695(5) Uani 1 1 d . . . H14 H 0.1226 -0.0188 0.3784 0.083 Uiso 1 1 calc R . . C15 C 0.19482(10) 0.56624(19) 0.36921(17) 0.0721(5) Uani 1 1 d . . . H15 H 0.2055 0.5508 0.4373 0.086 Uiso 1 1 calc R . . C16 C 0.17861(10) 0.6781(2) 0.3319(2) 0.0837(7) Uani 1 1 d . . . H16 H 0.1779 0.7378 0.3743 0.100 Uiso 1 1 calc R . . C17 C 0.16348(9) 0.70176(19) 0.2321(2) 0.0799(6) Uani 1 1 d . . . H17 H 0.1527 0.7776 0.2067 0.096 Uiso 1 1 calc R . . C18 C 0.16425(8) 0.61245(18) 0.16852(16) 0.0696(5) Uani 1 1 d . . . H18 H 0.1537 0.6293 0.1007 0.083 Uiso 1 1 calc R . . C19 C 0.11978(8) 0.30725(16) 0.35656(13) 0.0579(4) Uani 1 1 d . . . C20 C 0.04810(12) 0.2552(3) 0.4116(2) 0.0942(7) Uani 1 1 d . . . H20A H 0.0443 0.3325 0.4340 0.141 Uiso 1 1 calc R . . H20B H 0.0428 0.1976 0.4542 0.141 Uiso 1 1 calc R . . H20C H 0.0179 0.2442 0.3421 0.141 Uiso 1 1 calc R . . C21 C 0.08776(8) 0.29894(16) 0.00843(12) 0.0557(4) Uani 1 1 d . . . C22 C 0.00464(11) 0.4048(2) -0.11582(15) 0.0864(7) Uani 1 1 d . . . H22A H 0.0241 0.4273 -0.1559 0.130 Uiso 1 1 calc R . . H22B H -0.0228 0.4655 -0.1190 0.130 Uiso 1 1 calc R . . H22C H -0.0172 0.3329 -0.1422 0.130 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 O1 0.1164(13) 0.0951(11) 0.0483(7) -0.0147(7) 0.0254(8) 0.0123(9) O2 0.0724(9) 0.0809(9) 0.0458(7) 0.0001(6) 0.0127(6) 0.0102(7) O3 0.0675(9) 0.1080(12) 0.1079(12) 0.0434(10) 0.0472(9) 0.0232(8) O4 0.0870(10) 0.0885(10) 0.0710(9) 0.0153(7) 0.0503(8) 0.0102(8) C1 0.0518(9) 0.0653(10) 0.0393(8) -0.0009(7) 0.0225(7) -0.0031(7) C2 0.0559(10) 0.0715(11) 0.0518(9) -0.0011(8) 0.0272(8) 0.0059(8) C3 0.0531(9) 0.0545(9) 0.0565(10) 0.0021(7) 0.0248(8) 0.0104(7) C4 0.0592(10) 0.0542(9) 0.0566(10) 0.0064(8) 0.0263(8) 0.0134(8) C5 0.0641(11) 0.0704(12) 0.0486(9) 0.0084(8) 0.0207(8) 0.0115(9) C6 0.0553(9) 0.0666(10) 0.0361(8) 0.0004(7) 0.0159(7) 0.0031(8) C7 0.0480(9) 0.0714(11) 0.0425(8) -0.0024(8) 0.0156(7) 0.0020(8) C8 0.0461(9) 0.0651(10) 0.0590(10) -0.0063(8) 0.0264(8) -0.0054(8) C9 0.0406(8) 0.0640(10) 0.0573(10) 0.0008(8) 0.0227(7) -0.0067(7) C10 0.0555(10) 0.0821(12) 0.0493(9) 0.0000(8) 0.0284(8) -0.0099(9) C11 0.0674(12) 0.0628(11) 0.0602(11) -0.0006(9) 0.0223(9) 0.0068(9) C12 0.0667(12) 0.0583(11) 0.0889(15) -0.0053(10) 0.0251(11) -0.0018(9) C13 0.0817(14) 0.0592(11) 0.0965(16) 0.0036(11) 0.0491(13) -0.0003(10) C14 0.0848(14) 0.0597(11) 0.0724(12) 0.0101(9) 0.0435(11) 0.0119(10) C15 0.0747(13) 0.0766(13) 0.0768(13) -0.0122(11) 0.0452(11) -0.0079(10) C16 0.0826(15) 0.0739(14) 0.1128(19) -0.0155(13) 0.0608(14) -0.0026(11) C17 0.0599(12) 0.0649(12) 0.1163(19) 0.0082(12) 0.0421(12) 0.0060(9) C18 0.0473(10) 0.0819(14) 0.0764(13) 0.0146(10) 0.0260(9) -0.0032(9) C19 0.0600(10) 0.0644(11) 0.0486(9) 0.0003(8) 0.0246(8) 0.0007(8) C20 0.0873(16) 0.119(2) 0.0995(17) 0.0169(14) 0.0632(15) 0.0018(14) C21 0.0603(10) 0.0650(10) 0.0424(9) -0.0013(8) 0.0242(8) -0.0060(8) C22 0.0819(15) 0.0924(16) 0.0534(11) 0.0105(10) 0.0047(10) -0.0003(12) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C21 1.194(2) . ? O2 C21 1.326(2) . ? O2 C22 1.451(2) . ? O3 C19 1.203(2) . ? O4 C19 1.319(2) . ? O4 C20 1.449(3) . ? C1 C21 1.511(2) . ? C1 C2 1.544(2) . ? C1 C10 1.565(2) . ? C1 H1 0.9800 . ? C2 C3 1.509(2) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 C11 1.393(3) . ? C3 C4 1.409(2) . ? C4 C14 1.388(3) . ? C4 C5 1.520(3) . ? C5 C6 1.513(3) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 C7 1.328(2) . ? C6 C19 1.490(2) . ? C7 C8 1.480(3) . ? C7 H7 0.9300 . ? C8 C15 1.384(3) . ? C8 C9 1.403(2) . ? C9 C18 1.391(3) . ? C9 C10 1.508(2) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 C12 1.379(3) . ? C11 H11 0.9300 . ? C12 C13 1.366(3) . ? C12 H12 0.9300 . ? C13 C14 1.370(3) . ? C13 H13 0.9300 . ? C14 H14 0.9300 . ? C15 C16 1.372(3) . ? C15 H15 0.9300 . ? C16 C17 1.369(3) . ? C16 H16 0.9300 . ? C17 C18 1.390(3) . ? C17 H17 0.9300 . ? C18 H18 0.9300 . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 0.9600 . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 0.9600 . ? 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 C21 O2 C22 117.09(16) . . ? C19 O4 C20 117.24(16) . . ? C21 C1 C2 111.89(14) . . ? C21 C1 C10 108.71(13) . . ? C2 C1 C10 113.15(14) . . ? C21 C1 H1 107.6 . . ? C2 C1 H1 107.6 . . ? C10 C1 H1 107.6 . . ? C3 C2 C1 114.63(14) . . ? C3 C2 H2A 108.6 . . ? C1 C2 H2A 108.6 . . ? C3 C2 H2B 108.6 . . ? C1 C2 H2B 108.6 . . ? H2A C2 H2B 107.6 . . ? C11 C3 C4 117.86(17) . . ? C11 C3 C2 119.45(16) . . ? C4 C3 C2 122.69(16) . . ? C14 C4 C3 118.77(18) . . ? C14 C4 C5 118.50(17) . . ? C3 C4 C5 122.73(16) . . ? C6 C5 C4 110.76(14) . . ? C6 C5 H5A 109.5 . . ? C4 C5 H5A 109.5 . . ? C6 C5 H5B 109.5 . . ? C4 C5 H5B 109.5 . . ? H5A C5 H5B 108.1 . . ? C7 C6 C19 121.39(16) . . ? C7 C6 C5 121.94(17) . . ? C19 C6 C5 116.11(16) . . ? C6 C7 C8 127.96(16) . . ? C6 C7 H7 116.0 . . ? C8 C7 H7 116.0 . . ? C15 C8 C9 120.11(18) . . ? C15 C8 C7 122.81(17) . . ? C9 C8 C7 117.08(15) . . ? C18 C9 C8 117.88(17) . . ? C18 C9 C10 121.24(17) . . ? C8 C9 C10 120.86(16) . . ? C9 C10 C1 115.04(13) . . ? C9 C10 H10A 108.5 . . ? C1 C10 H10A 108.5 . . ? C9 C10 H10B 108.5 . . ? C1 C10 H10B 108.5 . . ? H10A C10 H10B 107.5 . . ? C12 C11 C3 121.88(19) . . ? C12 C11 H11 119.1 . . ? C3 C11 H11 119.1 . . ? C13 C12 C11 119.9(2) . . ? C13 C12 H12 120.1 . . ? C11 C12 H12 120.1 . . ? C12 C13 C14 119.5(2) . . ? C12 C13 H13 120.2 . . ? C14 C13 H13 120.2 . . ? C13 C14 C4 122.1(2) . . ? C13 C14 H14 119.0 . . ? C4 C14 H14 119.0 . . ? C16 C15 C8 121.0(2) . . ? C16 C15 H15 119.5 . . ? C8 C15 H15 119.5 . . ? C17 C16 C15 119.9(2) . . ? C17 C16 H16 120.1 . . ? C15 C16 H16 120.1 . . ? C16 C17 C18 120.0(2) . . ? C16 C17 H17 120.0 . . ? C18 C17 H17 120.0 . . ? C17 C18 C9 121.1(2) . . ? C17 C18 H18 119.4 . . ? C9 C18 H18 119.4 . . ? O3 C19 O4 122.95(17) . . ? O3 C19 C6 125.07(16) . . ? O4 C19 C6 111.85(15) . . ? O4 C20 H20A 109.5 . . ? O4 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? O4 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? O1 C21 O2 122.77(16) . . ? O1 C21 C1 126.01(17) . . ? O2 C21 C1 111.21(14) . . ? O2 C22 H22A 109.5 . . ? O2 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? O2 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C21 C1 C2 C3 -84.26(17) . . . . ? C10 C1 C2 C3 152.53(14) . . . . ? C1 C2 C3 C11 85.14(19) . . . . ? C1 C2 C3 C4 -94.32(19) . . . . ? C11 C3 C4 C14 0.7(2) . . . . ? C2 C3 C4 C14 -179.79(16) . . . . ? C11 C3 C4 C5 -178.78(16) . . . . ? C2 C3 C4 C5 0.7(2) . . . . ? C14 C4 C5 C6 -116.76(18) . . . . ? C3 C4 C5 C6 62.8(2) . . . . ? C4 C5 C6 C7 -113.93(18) . . . . ? C4 C5 C6 C19 57.6(2) . . . . ? C19 C6 C7 C8 -6.3(3) . . . . ? C5 C6 C7 C8 164.83(16) . . . . ? C6 C7 C8 C15 75.1(2) . . . . ? C6 C7 C8 C9 -104.9(2) . . . . ? C15 C8 C9 C18 -0.9(2) . . . . ? C7 C8 C9 C18 179.13(15) . . . . ? C15 C8 C9 C10 -179.73(16) . . . . ? C7 C8 C9 C10 0.3(2) . . . . ? C18 C9 C10 C1 -117.17(17) . . . . ? C8 C9 C10 C1 61.7(2) . . . . ? C21 C1 C10 C9 113.60(16) . . . . ? C2 C1 C10 C9 -121.44(16) . . . . ? C4 C3 C11 C12 0.4(3) . . . . ? C2 C3 C11 C12 -179.11(17) . . . . ? C3 C11 C12 C13 -1.2(3) . . . . ? C11 C12 C13 C14 0.9(3) . . . . ? C12 C13 C14 C4 0.3(3) . . . . ? C3 C4 C14 C13 -1.1(3) . . . . ? C5 C4 C14 C13 178.45(18) . . . . ? C9 C8 C15 C16 0.9(3) . . . . ? C7 C8 C15 C16 -179.05(18) . . . . ? C8 C15 C16 C17 -0.7(3) . . . . ? C15 C16 C17 C18 0.3(3) . . . . ? C16 C17 C18 C9 -0.3(3) . . . . ? C8 C9 C18 C17 0.5(3) . . . . ? C10 C9 C18 C17 179.39(16) . . . . ? C20 O4 C19 O3 3.0(3) . . . . ? C20 O4 C19 C6 -173.01(18) . . . . ? C7 C6 C19 O3 33.0(3) . . . . ? C5 C6 C19 O3 -138.6(2) . . . . ? C7 C6 C19 O4 -151.12(16) . . . . ? C5 C6 C19 O4 37.3(2) . . . . ? C22 O2 C21 O1 -4.4(3) . . . . ? C22 O2 C21 C1 174.62(16) . . . . ? C2 C1 C21 O1 -20.3(2) . . . . ? C10 C1 C21 O1 105.4(2) . . . . ? C2 C1 C21 O2 160.75(14) . . . . ? C10 C1 C21 O2 -73.56(18) . . . . ? _diffrn_measured_fraction_theta_max 0.973 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.269 _refine_diff_density_min -0.241 _refine_diff_density_rms 0.034 #===END # #gg1303bsm # # data_3 _database_code_depnum_ccdc_archive 'CCDC 295163' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C22 H22 O4' _chemical_formula_sum 'C22 H22 O4' _chemical_formula_weight 350.40 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 14.8162(12) _cell_length_b 14.8987(12) _cell_length_c 8.3482(7) _cell_angle_alpha 90.00 _cell_angle_beta 90.134(2) _cell_angle_gamma 90.00 _cell_volume 1842.8(3) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 2649 _cell_measurement_theta_min 2.73 _cell_measurement_theta_max 22.35 _exptl_crystal_description tablet _exptl_crystal_colour colorless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.263 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 744 _exptl_absorpt_coefficient_mu 0.086 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9415 _exptl_absorpt_correction_T_max 0.9872 _exptl_absorpt_process_details 'Sadabs (Bruker)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16259 _diffrn_reflns_av_R_equivalents 0.0477 _diffrn_reflns_av_sigmaI/netI 0.0625 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 1.94 _diffrn_reflns_theta_max 28.30 _reflns_number_total 4455 _reflns_number_gt 2043 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0693P)^2^+0.0980P] 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 constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0051(14) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4455 _refine_ls_number_parameters 238 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1383 _refine_ls_R_factor_gt 0.0521 _refine_ls_wR_factor_ref 0.1538 _refine_ls_wR_factor_gt 0.1212 _refine_ls_goodness_of_fit_ref 0.992 _refine_ls_restrained_S_all 0.992 _refine_ls_shift/su_max 0.004 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.70884(12) 0.37271(10) 0.5743(2) 0.0880(6) Uani 1 1 d . . . O2 O 0.81678(11) 0.36211(11) 0.3921(2) 0.0847(5) Uani 1 1 d . . . O3 O 0.87949(10) 0.47923(11) 0.06296(17) 0.0725(5) Uani 1 1 d . . . O4 O 0.73919(11) 0.43220(12) 0.0599(2) 0.0911(6) Uani 1 1 d . . . C1 C 0.87914(12) 0.55567(13) 0.3444(2) 0.0510(5) Uani 1 1 d . . . H1A H 0.9132 0.5002 0.3508 0.061 Uiso 1 1 calc R . . H1B H 0.9114 0.5957 0.2730 0.061 Uiso 1 1 calc R . . C2 C 0.87667(12) 0.59742(13) 0.5080(2) 0.0495(5) Uani 1 1 d . . . C3 C 0.95487(14) 0.63579(14) 0.5698(3) 0.0602(6) Uani 1 1 d . . . H3 H 1.0070 0.6360 0.5079 0.072 Uiso 1 1 calc R . . C4 C 0.95716(17) 0.67322(15) 0.7197(3) 0.0688(6) Uani 1 1 d . . . H4 H 1.0103 0.6981 0.7589 0.083 Uiso 1 1 calc R . . C5 C 0.88009(18) 0.67369(15) 0.8119(3) 0.0717(7) Uani 1 1 d . . . H5 H 0.8809 0.6995 0.9133 0.086 Uiso 1 1 calc R . . C6 C 0.80179(15) 0.63574(14) 0.7532(3) 0.0629(6) Uani 1 1 d . . . H6 H 0.7501 0.6357 0.8161 0.075 Uiso 1 1 calc R . . C7 C 0.79907(13) 0.59753(13) 0.6011(2) 0.0509(5) Uani 1 1 d . . . C8 C 0.71197(13) 0.55872(13) 0.5383(2) 0.0551(5) Uani 1 1 d . . . H8A H 0.6730 0.6079 0.5064 0.066 Uiso 1 1 calc R . . H8B H 0.6823 0.5273 0.6252 0.066 Uiso 1 1 calc R . . C9 C 0.72067(12) 0.49394(13) 0.3962(2) 0.0484(5) Uani 1 1 d . . . C10 C 0.75642(15) 0.40373(14) 0.4531(3) 0.0565(5) Uani 1 1 d . . . C11 C 0.7328(2) 0.28526(16) 0.6367(3) 0.1052(10) Uani 1 1 d . . . H11A H 0.7282 0.2414 0.5528 0.158 Uiso 1 1 calc R . . H11B H 0.6925 0.2696 0.7221 0.158 Uiso 1 1 calc R . . H11C H 0.7936 0.2867 0.6765 0.158 Uiso 1 1 calc R . . C12 C 0.62526(13) 0.47854(14) 0.3263(3) 0.0581(6) Uani 1 1 d . . . H12A H 0.6264 0.4252 0.2598 0.070 Uiso 1 1 calc R . . H12B H 0.5839 0.4673 0.4139 0.070 Uiso 1 1 calc R . . C13 C 0.58975(13) 0.55579(14) 0.2282(2) 0.0579(5) Uani 1 1 d . . . C14 C 0.49825(15) 0.55871(19) 0.1876(3) 0.0767(7) Uani 1 1 d . . . H14 H 0.4595 0.5144 0.2252 0.092 Uiso 1 1 calc R . . C15 C 0.46479(18) 0.6267(2) 0.0922(4) 0.0939(9) Uani 1 1 d . . . H15 H 0.4037 0.6280 0.0665 0.113 Uiso 1 1 calc R . . C16 C 0.5208(2) 0.6924(2) 0.0350(4) 0.0982(9) Uani 1 1 d . . . H16 H 0.4980 0.7385 -0.0283 0.118 Uiso 1 1 calc R . . C17 C 0.61096(16) 0.68942(16) 0.0719(3) 0.0764(7) Uani 1 1 d . . . H17 H 0.6492 0.7334 0.0315 0.092 Uiso 1 1 calc R . . C18 C 0.64664(13) 0.62196(14) 0.1688(2) 0.0565(5) Uani 1 1 d . . . C19 C 0.74523(12) 0.62424(13) 0.2104(2) 0.0545(5) Uani 1 1 d . . . H19A H 0.7544 0.6694 0.2926 0.065 Uiso 1 1 calc R . . H19B H 0.7784 0.6433 0.1164 0.065 Uiso 1 1 calc R . . C20 C 0.78614(12) 0.53512(12) 0.2701(2) 0.0466(5) Uani 1 1 d . . . C21 C 0.79745(14) 0.47463(14) 0.1238(2) 0.0542(5) Uani 1 1 d . . . C22 C 0.89658(17) 0.42768(18) -0.0805(3) 0.0869(8) Uani 1 1 d . . . H22A H 0.8927 0.3648 -0.0563 0.130 Uiso 1 1 calc R . . H22B H 0.9558 0.4413 -0.1199 0.130 Uiso 1 1 calc R . . H22C H 0.8525 0.4427 -0.1607 0.130 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 O1 0.1262(15) 0.0610(10) 0.0771(11) 0.0172(9) 0.0289(11) 0.0088(10) O2 0.0732(11) 0.0640(10) 0.1170(14) 0.0135(10) 0.0150(10) 0.0099(9) O3 0.0580(10) 0.0959(12) 0.0637(9) -0.0229(8) 0.0122(7) -0.0152(8) O4 0.0620(11) 0.1099(14) 0.1013(13) -0.0485(11) 0.0061(9) -0.0209(10) C1 0.0417(11) 0.0541(12) 0.0570(12) -0.0013(10) -0.0014(9) -0.0018(9) C2 0.0484(12) 0.0457(11) 0.0543(12) 0.0015(9) -0.0081(10) -0.0004(9) C3 0.0543(13) 0.0619(13) 0.0645(14) 0.0054(11) -0.0135(11) -0.0026(11) C4 0.0704(16) 0.0654(15) 0.0705(16) 0.0028(12) -0.0268(13) -0.0085(12) C5 0.0924(19) 0.0620(15) 0.0607(14) -0.0073(12) -0.0146(14) -0.0015(13) C6 0.0709(15) 0.0576(13) 0.0601(14) -0.0043(11) -0.0026(11) -0.0004(11) C7 0.0550(12) 0.0448(11) 0.0529(12) 0.0014(9) -0.0048(10) 0.0021(9) C8 0.0525(12) 0.0540(12) 0.0588(13) -0.0006(10) 0.0051(10) -0.0023(10) C9 0.0457(11) 0.0477(12) 0.0518(12) -0.0002(9) 0.0003(9) -0.0056(9) C10 0.0575(13) 0.0501(13) 0.0619(14) -0.0022(11) -0.0021(11) -0.0076(11) C11 0.163(3) 0.0595(17) 0.093(2) 0.0252(15) 0.0071(19) 0.0058(17) C12 0.0467(12) 0.0624(14) 0.0651(13) -0.0055(11) 0.0042(10) -0.0100(10) C13 0.0444(12) 0.0659(14) 0.0635(13) -0.0088(11) -0.0059(10) 0.0019(10) C14 0.0485(14) 0.0927(18) 0.0888(17) -0.0156(15) -0.0052(12) 0.0000(13) C15 0.0577(16) 0.113(2) 0.111(2) -0.0213(19) -0.0306(15) 0.0222(17) C16 0.085(2) 0.094(2) 0.116(2) -0.0031(18) -0.0373(17) 0.0243(18) C17 0.0736(17) 0.0694(16) 0.0861(17) 0.0038(13) -0.0177(13) 0.0109(13) C18 0.0496(12) 0.0569(13) 0.0631(13) -0.0047(11) -0.0070(10) 0.0034(10) C19 0.0520(12) 0.0536(13) 0.0579(12) 0.0029(10) -0.0012(10) -0.0061(9) C20 0.0407(11) 0.0474(11) 0.0517(11) -0.0015(9) -0.0024(9) -0.0022(8) C21 0.0463(12) 0.0540(13) 0.0622(13) -0.0027(10) -0.0022(10) -0.0035(10) C22 0.0818(17) 0.109(2) 0.0701(16) -0.0302(15) 0.0170(13) -0.0091(15) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C10 1.318(2) . ? O1 C11 1.447(3) . ? O2 C10 1.202(2) . ? O3 C21 1.320(2) . ? O3 C22 1.446(2) . ? O4 C21 1.194(2) . ? C1 C2 1.501(3) . ? C1 C20 1.540(2) . ? C1 H1A 0.9700 . ? C1 H1B 0.9700 . ? C2 C7 1.389(3) . ? C2 C3 1.390(3) . ? C3 C4 1.370(3) . ? C3 H3 0.9300 . ? C4 C5 1.379(3) . ? C4 H4 0.9300 . ? C5 C6 1.380(3) . ? C5 H5 0.9300 . ? C6 C7 1.392(3) . ? C6 H6 0.9300 . ? C7 C8 1.507(3) . ? C8 C9 1.535(3) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 C10 1.520(3) . ? C9 C12 1.545(3) . ? C9 C20 1.559(3) . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C12 C13 1.507(3) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 C18 1.389(3) . ? C13 C14 1.397(3) . ? C14 C15 1.380(4) . ? C14 H14 0.9300 . ? C15 C16 1.370(4) . ? C15 H15 0.9300 . ? C16 C17 1.371(3) . ? C16 H16 0.9300 . ? C17 C18 1.393(3) . ? C17 H17 0.9300 . ? C18 C19 1.501(3) . ? C19 C20 1.542(3) . ? C19 H19A 0.9700 . ? C19 H19B 0.9700 . ? C20 C21 1.528(3) . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 0.9600 . ? 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 C10 O1 C11 117.42(19) . . ? C21 O3 C22 117.02(16) . . ? C2 C1 C20 115.14(15) . . ? C2 C1 H1A 108.5 . . ? C20 C1 H1A 108.5 . . ? C2 C1 H1B 108.5 . . ? C20 C1 H1B 108.5 . . ? H1A C1 H1B 107.5 . . ? C7 C2 C3 118.80(19) . . ? C7 C2 C1 122.11(17) . . ? C3 C2 C1 119.08(17) . . ? C4 C3 C2 121.7(2) . . ? C4 C3 H3 119.2 . . ? C2 C3 H3 119.2 . . ? C3 C4 C5 119.6(2) . . ? C3 C4 H4 120.2 . . ? C5 C4 H4 120.2 . . ? C4 C5 C6 119.8(2) . . ? C4 C5 H5 120.1 . . ? C6 C5 H5 120.1 . . ? C5 C6 C7 120.9(2) . . ? C5 C6 H6 119.5 . . ? C7 C6 H6 119.5 . . ? C2 C7 C6 119.25(18) . . ? C2 C7 C8 120.93(17) . . ? C6 C7 C8 119.81(18) . . ? C7 C8 C9 115.89(16) . . ? C7 C8 H8A 108.3 . . ? C9 C8 H8A 108.3 . . ? C7 C8 H8B 108.3 . . ? C9 C8 H8B 108.3 . . ? H8A C8 H8B 107.4 . . ? C10 C9 C8 110.13(16) . . ? C10 C9 C12 107.72(16) . . ? C8 C9 C12 107.85(15) . . ? C10 C9 C20 110.00(16) . . ? C8 C9 C20 109.14(15) . . ? C12 C9 C20 111.96(15) . . ? O2 C10 O1 122.9(2) . . ? O2 C10 C9 125.6(2) . . ? O1 C10 C9 111.30(19) . . ? O1 C11 H11A 109.5 . . ? O1 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? O1 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C13 C12 C9 114.19(16) . . ? C13 C12 H12A 108.7 . . ? C9 C12 H12A 108.7 . . ? C13 C12 H12B 108.7 . . ? C9 C12 H12B 108.7 . . ? H12A C12 H12B 107.6 . . ? C18 C13 C14 118.7(2) . . ? C18 C13 C12 121.64(18) . . ? C14 C13 C12 119.5(2) . . ? C15 C14 C13 120.6(2) . . ? C15 C14 H14 119.7 . . ? C13 C14 H14 119.7 . . ? C16 C15 C14 120.6(2) . . ? C16 C15 H15 119.7 . . ? C14 C15 H15 119.7 . . ? C17 C16 C15 119.3(3) . . ? C17 C16 H16 120.4 . . ? C15 C16 H16 120.4 . . ? C16 C17 C18 121.5(3) . . ? C16 C17 H17 119.3 . . ? C18 C17 H17 119.3 . . ? C13 C18 C17 119.3(2) . . ? C13 C18 C19 121.63(18) . . ? C17 C18 C19 119.1(2) . . ? C18 C19 C20 115.91(16) . . ? C18 C19 H19A 108.3 . . ? C20 C19 H19A 108.3 . . ? C18 C19 H19B 108.3 . . ? C20 C19 H19B 108.3 . . ? H19A C19 H19B 107.4 . . ? C21 C20 C1 109.85(15) . . ? C21 C20 C19 107.07(15) . . ? C1 C20 C19 108.03(15) . . ? C21 C20 C9 112.17(15) . . ? C1 C20 C9 111.34(15) . . ? C19 C20 C9 108.20(15) . . ? O4 C21 O3 121.38(19) . . ? O4 C21 C20 126.07(19) . . ? O3 C21 C20 112.32(17) . . ? O3 C22 H22A 109.5 . . ? O3 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? O3 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C20 C1 C2 C7 14.9(3) . . . . ? C20 C1 C2 C3 -166.29(17) . . . . ? C7 C2 C3 C4 0.2(3) . . . . ? C1 C2 C3 C4 -178.64(19) . . . . ? C2 C3 C4 C5 -0.4(3) . . . . ? C3 C4 C5 C6 0.7(3) . . . . ? C4 C5 C6 C7 -0.6(3) . . . . ? C3 C2 C7 C6 -0.1(3) . . . . ? C1 C2 C7 C6 178.67(18) . . . . ? C3 C2 C7 C8 178.59(18) . . . . ? C1 C2 C7 C8 -2.6(3) . . . . ? C5 C6 C7 C2 0.3(3) . . . . ? C5 C6 C7 C8 -178.39(19) . . . . ? C2 C7 C8 C9 19.2(3) . . . . ? C6 C7 C8 C9 -162.08(18) . . . . ? C7 C8 C9 C10 75.1(2) . . . . ? C7 C8 C9 C12 -167.61(16) . . . . ? C7 C8 C9 C20 -45.8(2) . . . . ? C11 O1 C10 O2 1.2(3) . . . . ? C11 O1 C10 C9 177.38(19) . . . . ? C8 C9 C10 O2 -132.4(2) . . . . ? C12 C9 C10 O2 110.2(2) . . . . ? C20 C9 C10 O2 -12.1(3) . . . . ? C8 C9 C10 O1 51.6(2) . . . . ? C12 C9 C10 O1 -65.8(2) . . . . ? C20 C9 C10 O1 171.89(16) . . . . ? C10 C9 C12 C13 -165.52(17) . . . . ? C8 C9 C12 C13 75.6(2) . . . . ? C20 C9 C12 C13 -44.4(2) . . . . ? C9 C12 C13 C18 17.4(3) . . . . ? C9 C12 C13 C14 -166.34(18) . . . . ? C18 C13 C14 C15 -0.9(3) . . . . ? C12 C13 C14 C15 -177.3(2) . . . . ? C13 C14 C15 C16 0.3(4) . . . . ? C14 C15 C16 C17 0.7(4) . . . . ? C15 C16 C17 C18 -1.2(4) . . . . ? C14 C13 C18 C17 0.5(3) . . . . ? C12 C13 C18 C17 176.77(19) . . . . ? C14 C13 C18 C19 178.60(19) . . . . ? C12 C13 C18 C19 -5.1(3) . . . . ? C16 C17 C18 C13 0.6(3) . . . . ? C16 C17 C18 C19 -177.6(2) . . . . ? C13 C18 C19 C20 20.6(3) . . . . ? C17 C18 C19 C20 -161.31(19) . . . . ? C2 C1 C20 C21 -167.30(16) . . . . ? C2 C1 C20 C19 76.2(2) . . . . ? C2 C1 C20 C9 -42.4(2) . . . . ? C18 C19 C20 C21 75.3(2) . . . . ? C18 C19 C20 C1 -166.44(16) . . . . ? C18 C19 C20 C9 -45.8(2) . . . . ? C10 C9 C20 C21 59.7(2) . . . . ? C8 C9 C20 C21 -179.40(15) . . . . ? C12 C9 C20 C21 -60.1(2) . . . . ? C10 C9 C20 C1 -63.89(19) . . . . ? C8 C9 C20 C1 57.0(2) . . . . ? C12 C9 C20 C1 176.37(16) . . . . ? C10 C9 C20 C19 177.55(15) . . . . ? C8 C9 C20 C19 -61.53(19) . . . . ? C12 C9 C20 C19 57.80(19) . . . . ? C22 O3 C21 O4 -2.5(3) . . . . ? C22 O3 C21 C20 -177.28(18) . . . . ? C1 C20 C21 O4 163.7(2) . . . . ? C19 C20 C21 O4 -79.2(3) . . . . ? C9 C20 C21 O4 39.3(3) . . . . ? C1 C20 C21 O3 -21.8(2) . . . . ? C19 C20 C21 O3 95.27(19) . . . . ? C9 C20 C21 O3 -146.19(17) . . . . ? _diffrn_measured_fraction_theta_max 0.972 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.266 _refine_diff_density_min -0.145 _refine_diff_density_rms 0.032 #===END