# Supplementary Material (ESI) for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 0182 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'William Jones' _publ_contact_author_email WJ10@CAM.AC.UK _publ_section_title ; New solid forms of artemisinin ; loop_ _publ_author_name 'William Jones' 'Laszlo Fabian' 'Tomislav Friscic' 'Shyam Karki' # Attachment 'deposit.cif' data_art-res _database_code_depnum_ccdc_archive 'CCDC 735601' _audit_creation_method SHELXL-97 _chemical_name_systematic ; artemisinin-resorcinol 2/1 ; _chemical_name_common 'artemisinin-resorcinol 2/1' _chemical_melting_point ? _chemical_formula_moiety '2(C15 H22 O5), C6 H6 O2' _chemical_formula_sum 'C36 H50 O12' _chemical_formula_weight 674.76 _chemical_absolute_configuration ; 3201 Friedel pairs were averaged for the refinement. ; 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 P2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 9.5298(2) _cell_length_b 17.3699(4) _cell_length_c 10.4197(3) _cell_angle_alpha 90.00 _cell_angle_beta 94.0170(10) _cell_angle_gamma 90.00 _cell_volume 1720.55(7) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 31872 _cell_measurement_theta_min 1.02 _cell_measurement_theta_max 27.88 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.302 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 724 _exptl_absorpt_coefficient_mu 0.097 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.758 _exptl_absorpt_correction_T_max 0.995 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; The -OH hydrogen atoms were located and their positions were refined satisfactorily. The absolute structure was assigned from the known configuration of the starting material. ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method 'Thin slice \w and \f scans' _diffrn_reflns_number 15215 _diffrn_reflns_av_R_equivalents 0.0530 _diffrn_reflns_av_sigmaI/netI 0.0388 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 3.65 _diffrn_reflns_theta_max 27.90 _reflns_number_total 4183 _reflns_number_gt 3893 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V. 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor 1997) ; _computing_structure_solution 'SIR-92 (Altomare et al. 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick 1997)' _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^)+(0.0598P)^2^+0.1989P] 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 0.6(7) _refine_ls_number_reflns 4183 _refine_ls_number_parameters 445 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0421 _refine_ls_R_factor_gt 0.0385 _refine_ls_wR_factor_ref 0.1016 _refine_ls_wR_factor_gt 0.0984 _refine_ls_goodness_of_fit_ref 1.036 _refine_ls_restrained_S_all 1.036 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O -0.17878(17) 0.49046(12) 0.86954(17) 0.0518(5) Uani 1 1 d . . . O2 O 0.02538(15) 0.43780(10) 0.84953(15) 0.0374(3) Uani 1 1 d . . . O3 O 0.25336(15) 0.40288(8) 0.89295(14) 0.0322(3) Uani 1 1 d . . . O4 O 0.24906(16) 0.56278(8) 0.82476(15) 0.0369(3) Uani 1 1 d . . . O5 O 0.25872(16) 0.53073(9) 0.95541(14) 0.0382(3) Uani 1 1 d . . . O6 O -0.1614(2) 0.31953(13) 0.51656(19) 0.0556(5) Uani 1 1 d . . . H6A H -0.101(4) 0.286(2) 0.552(4) 0.067 Uiso 1 1 d . . . O7 O -0.23861(18) 0.43718(11) 0.11118(18) 0.0452(4) Uani 1 1 d . . . H7A H -0.213(3) 0.443(2) 0.036(3) 0.054 Uiso 1 1 d . . . O8 O -1.03941(18) 0.19267(16) -0.3515(2) 0.0705(7) Uani 1 1 d . . . O9 O -0.82353(15) 0.23284(9) -0.33786(16) 0.0377(3) Uani 1 1 d . . . O10 O -0.60743(15) 0.10027(8) -0.28878(15) 0.0346(3) Uani 1 1 d . . . O11 O -0.59500(15) 0.25637(8) -0.37481(15) 0.0344(3) Uani 1 1 d . . . O12 O -0.60509(16) 0.12665(9) -0.42273(16) 0.0386(3) Uani 1 1 d . . . C1 C -0.0693(2) 0.49296(14) 0.8178(2) 0.0375(5) Uani 1 1 d . . . C2 C -0.0347(2) 0.55696(13) 0.7272(2) 0.0377(5) Uani 1 1 d . . . H2 H -0.0038 0.6016 0.7829 0.045 Uiso 1 1 calc R . . C3 C 0.0888(2) 0.53895(12) 0.6447(2) 0.0333(4) Uani 1 1 d . . . H3 H 0.1236 0.5894 0.6133 0.040 Uiso 1 1 calc R . . C4 C 0.0533(2) 0.48935(13) 0.5261(2) 0.0384(5) Uani 1 1 d . . . H4A H 0.0173 0.4388 0.5529 0.046 Uiso 1 1 calc R . . H4B H -0.0215 0.5147 0.4704 0.046 Uiso 1 1 calc R . . C5 C 0.1828(3) 0.47741(14) 0.4506(2) 0.0421(5) Uani 1 1 d . . . H5A H 0.2132 0.5277 0.4175 0.050 Uiso 1 1 calc R . . H5B H 0.1576 0.4439 0.3757 0.050 Uiso 1 1 calc R . . C6 C 0.3056(2) 0.44101(13) 0.5318(2) 0.0380(4) Uani 1 1 d . . . H6 H 0.2755 0.3884 0.5575 0.046 Uiso 1 1 calc R . . C7 C 0.3412(2) 0.48752(12) 0.6561(2) 0.0335(4) Uani 1 1 d . . . H7 H 0.3773 0.5387 0.6291 0.040 Uiso 1 1 calc R . . C8 C 0.4604(2) 0.44950(13) 0.7413(2) 0.0388(5) Uani 1 1 d . . . H8A H 0.4470 0.3930 0.7367 0.047 Uiso 1 1 calc R . . H8B H 0.5506 0.4612 0.7037 0.047 Uiso 1 1 calc R . . C9 C 0.4744(2) 0.47264(14) 0.8834(2) 0.0402(5) Uani 1 1 d . . . H9A H 0.5502 0.4415 0.9276 0.048 Uiso 1 1 calc R . . H9B H 0.5038 0.5273 0.8894 0.048 Uiso 1 1 calc R . . C10 C 0.3410(2) 0.46282(12) 0.9548(2) 0.0355(4) Uani 1 1 d . . . C11 C 0.1605(2) 0.43054(11) 0.79431(19) 0.0298(4) Uani 1 1 d . . . H11 H 0.1507 0.3896 0.7267 0.036 Uiso 1 1 calc R . . C12 C 0.2097(2) 0.50347(11) 0.73006(19) 0.0298(4) Uani 1 1 d . . . C13 C -0.1682(3) 0.58336(18) 0.6489(3) 0.0530(6) Uani 1 1 d . . . H13A H -0.2349 0.6045 0.7071 0.079 Uiso 1 1 calc R . . H13B H -0.2111 0.5394 0.6021 0.079 Uiso 1 1 calc R . . H13C H -0.1439 0.6231 0.5875 0.079 Uiso 1 1 calc R . . C14 C 0.3656(3) 0.44152(15) 1.0952(2) 0.0439(5) Uani 1 1 d . . . H14A H 0.2757 0.4415 1.1354 0.066 Uiso 1 1 calc R . . H14B H 0.4293 0.4791 1.1386 0.066 Uiso 1 1 calc R . . H14C H 0.4078 0.3901 1.1025 0.066 Uiso 1 1 calc R . . C15 C 0.4338(3) 0.43190(17) 0.4530(3) 0.0517(6) Uani 1 1 d . . . H15A H 0.4078 0.4018 0.3754 0.078 Uiso 1 1 calc R . . H15B H 0.5087 0.4052 0.5047 0.078 Uiso 1 1 calc R . . H15C H 0.4672 0.4828 0.4285 0.078 Uiso 1 1 calc R . . C16 C -0.1176(3) 0.32889(14) 0.3952(2) 0.0416(5) Uani 1 1 d . . . C17 C -0.1961(2) 0.37815(14) 0.3130(2) 0.0391(5) Uani 1 1 d . . . H17 H -0.2768 0.4034 0.3412 0.047 Uiso 1 1 calc R . . C18 C -0.1550(2) 0.39001(13) 0.1892(2) 0.0364(4) Uani 1 1 d . . . C19 C -0.0365(3) 0.35441(16) 0.1479(2) 0.0445(5) Uani 1 1 d . . . H19 H -0.0087 0.3626 0.0632 0.053 Uiso 1 1 calc R . . C20 C 0.0408(3) 0.30668(17) 0.2324(3) 0.0543(7) Uani 1 1 d . . . H20 H 0.1231 0.2826 0.2050 0.065 Uiso 1 1 calc R . . C21 C 0.0014(3) 0.29302(16) 0.3561(3) 0.0497(6) Uani 1 1 d . . . H21 H 0.0552 0.2597 0.4127 0.060 Uiso 1 1 calc R . . C22 C -0.9225(2) 0.18402(16) -0.3026(2) 0.0421(5) Uani 1 1 d . . . C23 C -0.8833(2) 0.11835(13) -0.2120(2) 0.0350(4) Uani 1 1 d . . . H23 H -0.8580 0.0741 -0.2672 0.042 Uiso 1 1 calc R . . C24 C -0.7514(2) 0.13560(12) -0.1219(2) 0.0319(4) Uani 1 1 d . . . H24 H -0.7192 0.0856 -0.0823 0.038 Uiso 1 1 calc R . . C25 C -0.7745(2) 0.19127(14) -0.0117(2) 0.0378(4) Uani 1 1 d . . . H25A H -0.8080 0.2414 -0.0471 0.045 Uiso 1 1 calc R . . H25B H -0.8474 0.1704 0.0419 0.045 Uiso 1 1 calc R . . C26 C -0.6378(3) 0.20280(14) 0.0708(2) 0.0421(5) Uani 1 1 d . . . H26A H -0.6093 0.1532 0.1115 0.050 Uiso 1 1 calc R . . H26B H -0.6543 0.2399 0.1404 0.050 Uiso 1 1 calc R . . C27 C -0.5183(2) 0.23247(12) -0.0057(2) 0.0382(5) Uani 1 1 d . . . H27 H -0.5458 0.2846 -0.0397 0.046 Uiso 1 1 calc R . . C28 C -0.4947(2) 0.18013(12) -0.1220(2) 0.0345(4) Uani 1 1 d . . . H28 H -0.4597 0.1295 -0.0870 0.041 Uiso 1 1 calc R . . C29 C -0.6345(2) 0.16417(11) -0.2032(2) 0.0295(4) Uani 1 1 d . . . C30 C -0.68030(19) 0.23632(12) -0.2775(2) 0.0308(4) Uani 1 1 d . . . H30 H -0.6772 0.2799 -0.2147 0.037 Uiso 1 1 calc R . . C31 C -0.5170(2) 0.19256(13) -0.4231(2) 0.0382(5) Uani 1 1 d . . . C32 C -0.3793(2) 0.18131(15) -0.3406(3) 0.0441(5) Uani 1 1 d . . . H32A H -0.3575 0.1256 -0.3364 0.053 Uiso 1 1 calc R . . H32B H -0.3027 0.2070 -0.3837 0.053 Uiso 1 1 calc R . . C33 C -0.3808(2) 0.21238(14) -0.2037(3) 0.0420(5) Uani 1 1 d . . . H33A H -0.3921 0.2690 -0.2085 0.050 Uiso 1 1 calc R . . H33B H -0.2880 0.2018 -0.1585 0.050 Uiso 1 1 calc R . . C34 C -0.3837(3) 0.24182(17) 0.0828(3) 0.0522(6) Uani 1 1 d . . . H34A H -0.4036 0.2738 0.1568 0.078 Uiso 1 1 calc R . . H34B H -0.3109 0.2666 0.0351 0.078 Uiso 1 1 calc R . . H34C H -0.3507 0.1911 0.1129 0.078 Uiso 1 1 calc R . . C35 C -1.0109(2) 0.09226(16) -0.1415(3) 0.0449(5) Uani 1 1 d . . . H35A H -1.0859 0.0756 -0.2044 0.067 Uiso 1 1 calc R . . H35B H -1.0446 0.1352 -0.0910 0.067 Uiso 1 1 calc R . . H35C H -0.9836 0.0493 -0.0840 0.067 Uiso 1 1 calc R . . C36 C -0.4989(3) 0.20930(16) -0.5632(3) 0.0495(6) Uani 1 1 d . . . H36A H -0.5915 0.2122 -0.6102 0.074 Uiso 1 1 calc R . . H36B H -0.4437 0.1681 -0.5995 0.074 Uiso 1 1 calc R . . H36C H -0.4498 0.2585 -0.5707 0.074 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 0.0363(8) 0.0724(13) 0.0471(9) 0.0111(9) 0.0070(7) 0.0081(8) O2 0.0321(7) 0.0398(8) 0.0405(8) 0.0079(7) 0.0044(6) 0.0009(6) O3 0.0353(7) 0.0271(6) 0.0339(7) 0.0024(6) -0.0008(5) 0.0009(6) O4 0.0478(8) 0.0244(7) 0.0375(8) -0.0027(6) -0.0039(6) -0.0009(6) O5 0.0462(8) 0.0318(8) 0.0355(8) -0.0034(6) -0.0037(6) 0.0054(6) O6 0.0572(11) 0.0631(12) 0.0467(10) 0.0190(9) 0.0044(8) -0.0083(10) O7 0.0472(9) 0.0455(9) 0.0427(9) 0.0093(8) 0.0014(7) 0.0055(8) O8 0.0304(8) 0.1010(17) 0.0782(14) 0.0521(14) -0.0102(8) -0.0108(10) O9 0.0281(7) 0.0404(8) 0.0441(8) 0.0133(7) -0.0007(6) 0.0001(6) O10 0.0405(7) 0.0226(6) 0.0408(8) -0.0014(6) 0.0032(6) -0.0009(6) O11 0.0333(7) 0.0263(7) 0.0442(8) 0.0026(6) 0.0068(6) -0.0001(5) O12 0.0422(8) 0.0333(8) 0.0410(8) -0.0021(6) 0.0067(6) -0.0070(7) C1 0.0316(9) 0.0456(12) 0.0345(10) -0.0003(9) -0.0024(8) 0.0027(9) C2 0.0366(10) 0.0358(11) 0.0401(11) 0.0014(9) -0.0015(8) 0.0060(9) C3 0.0384(10) 0.0256(9) 0.0354(10) 0.0033(8) -0.0004(8) -0.0003(8) C4 0.0460(11) 0.0346(11) 0.0339(10) 0.0008(9) -0.0018(8) -0.0024(9) C5 0.0560(13) 0.0381(11) 0.0323(10) 0.0043(9) 0.0044(9) -0.0040(10) C6 0.0497(12) 0.0307(10) 0.0349(10) 0.0021(8) 0.0119(9) -0.0020(9) C7 0.0372(10) 0.0264(9) 0.0376(10) 0.0024(8) 0.0062(8) -0.0038(8) C8 0.0330(9) 0.0356(11) 0.0485(12) 0.0013(9) 0.0071(8) -0.0005(8) C9 0.0320(10) 0.0391(11) 0.0488(13) -0.0014(10) -0.0013(9) -0.0013(9) C10 0.0351(10) 0.0308(10) 0.0397(11) -0.0034(8) -0.0043(8) 0.0032(8) C11 0.0307(9) 0.0269(9) 0.0317(9) 0.0019(7) 0.0014(7) 0.0001(7) C12 0.0330(9) 0.0231(8) 0.0330(9) -0.0021(7) 0.0007(7) -0.0023(7) C13 0.0438(12) 0.0588(16) 0.0555(15) 0.0120(12) -0.0020(10) 0.0148(12) C14 0.0488(12) 0.0427(12) 0.0392(11) -0.0009(10) -0.0052(9) 0.0075(11) C15 0.0608(15) 0.0499(14) 0.0468(13) 0.0060(11) 0.0203(11) 0.0066(12) C16 0.0462(12) 0.0354(11) 0.0427(12) 0.0065(9) -0.0003(9) -0.0121(9) C17 0.0358(10) 0.0374(11) 0.0442(12) 0.0015(9) 0.0020(9) -0.0040(9) C18 0.0369(10) 0.0310(10) 0.0406(11) 0.0011(9) -0.0018(8) -0.0042(8) C19 0.0498(13) 0.0475(13) 0.0362(12) -0.0004(10) 0.0030(10) 0.0031(11) C20 0.0512(14) 0.0566(16) 0.0551(15) 0.0016(13) 0.0039(12) 0.0175(13) C21 0.0528(14) 0.0422(13) 0.0528(14) 0.0089(11) -0.0055(11) 0.0033(11) C22 0.0294(10) 0.0530(13) 0.0435(12) 0.0125(10) 0.0001(8) -0.0024(10) C23 0.0292(9) 0.0361(11) 0.0392(11) 0.0052(8) -0.0006(8) -0.0051(8) C24 0.0306(9) 0.0287(9) 0.0359(10) 0.0028(8) -0.0007(7) -0.0008(7) C25 0.0396(10) 0.0371(11) 0.0367(11) 0.0037(9) 0.0028(8) 0.0007(9) C26 0.0506(12) 0.0358(11) 0.0386(11) -0.0015(9) -0.0057(9) 0.0019(10) C27 0.0394(11) 0.0270(10) 0.0464(12) -0.0021(9) -0.0093(9) 0.0005(8) C28 0.0283(9) 0.0257(9) 0.0482(12) 0.0002(8) -0.0077(8) 0.0011(7) C29 0.0281(8) 0.0216(8) 0.0384(10) -0.0019(7) 0.0000(7) -0.0006(7) C30 0.0275(9) 0.0269(9) 0.0378(10) 0.0021(8) 0.0011(7) 0.0004(7) C31 0.0346(10) 0.0304(10) 0.0507(12) -0.0025(9) 0.0114(9) -0.0020(8) C32 0.0298(10) 0.0394(12) 0.0641(15) -0.0023(11) 0.0103(9) 0.0011(9) C33 0.0282(9) 0.0365(11) 0.0606(14) -0.0015(10) -0.0023(9) -0.0031(9) C34 0.0515(14) 0.0421(13) 0.0596(15) -0.0044(12) -0.0203(12) -0.0020(11) C35 0.0342(10) 0.0514(14) 0.0491(13) 0.0129(11) 0.0020(9) -0.0078(10) C36 0.0540(13) 0.0433(13) 0.0531(14) -0.0017(11) 0.0177(11) -0.0060(11) _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 C1 1.209(3) . ? O2 C1 1.341(3) . ? O2 C11 1.453(2) . ? O3 C11 1.394(2) . ? O3 C10 1.457(3) . ? O4 C12 1.457(2) . ? O4 O5 1.468(2) . ? O5 C10 1.417(3) . ? O6 C16 1.369(3) . ? O6 H6A 0.88(4) . ? O7 C18 1.369(3) . ? O7 H7A 0.84(4) . ? O8 C22 1.202(3) . ? O9 C22 1.338(3) . ? O9 C30 1.464(2) . ? O10 C29 1.458(2) . ? O10 O12 1.471(2) . ? O11 C30 1.387(3) . ? O11 C31 1.444(3) . ? O12 C31 1.420(3) . ? C1 C2 1.509(3) . ? C2 C13 1.533(3) . ? C2 C3 1.538(3) . ? C2 H2 1.0000 . ? C3 C4 1.525(3) . ? C3 C12 1.534(3) . ? C3 H3 1.0000 . ? C4 C5 1.524(3) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C6 1.531(3) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 C15 1.527(3) . ? C6 C7 1.544(3) . ? C6 H6 1.0000 . ? C7 C8 1.541(3) . ? C7 C12 1.542(3) . ? C7 H7 1.0000 . ? C8 C9 1.531(3) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 C10 1.527(3) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 C14 1.511(3) . ? C11 C12 1.522(3) . ? C11 H11 1.0000 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 C21 1.380(4) . ? C16 C17 1.391(3) . ? C17 C18 1.389(3) . ? C17 H17 0.9500 . ? C18 C19 1.382(4) . ? C19 C20 1.383(4) . ? C19 H19 0.9500 . ? C20 C21 1.388(4) . ? C20 H20 0.9500 . ? C21 H21 0.9500 . ? C22 C23 1.511(3) . ? C23 C35 1.532(3) . ? C23 C24 1.545(3) . ? C23 H23 1.0000 . ? C24 C25 1.529(3) . ? C24 C29 1.529(3) . ? C24 H24 1.0000 . ? C25 C26 1.523(3) . ? C25 H25A 0.9900 . ? C25 H25B 0.9900 . ? C26 C27 1.525(3) . ? C26 H26A 0.9900 . ? C26 H26B 0.9900 . ? C27 C34 1.534(3) . ? C27 C28 1.544(3) . ? C27 H27 1.0000 . ? C28 C33 1.531(3) . ? C28 C29 1.552(3) . ? C28 H28 1.0000 . ? C29 C30 1.521(3) . ? C30 H30 1.0000 . ? C31 C36 1.510(3) . ? C31 C32 1.530(3) . ? C32 C33 1.526(4) . ? C32 H32A 0.9900 . ? C32 H32B 0.9900 . ? C33 H33A 0.9900 . ? C33 H33B 0.9900 . ? C34 H34A 0.9800 . ? C34 H34B 0.9800 . ? C34 H34C 0.9800 . ? C35 H35A 0.9800 . ? C35 H35B 0.9800 . ? C35 H35C 0.9800 . ? C36 H36A 0.9800 . ? C36 H36B 0.9800 . ? C36 H36C 0.9800 . ? 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 C1 O2 C11 124.33(16) . . ? C11 O3 C10 113.23(15) . . ? C12 O4 O5 110.88(14) . . ? C10 O5 O4 108.07(15) . . ? C16 O6 H6A 104(2) . . ? C18 O7 H7A 115(2) . . ? C22 O9 C30 124.21(16) . . ? C29 O10 O12 110.98(14) . . ? C30 O11 C31 113.83(16) . . ? C31 O12 O10 107.59(15) . . ? O1 C1 O2 116.8(2) . . ? O1 C1 C2 122.6(2) . . ? O2 C1 C2 120.52(18) . . ? C1 C2 C13 110.10(19) . . ? C1 C2 C3 114.14(18) . . ? C13 C2 C3 113.73(19) . . ? C1 C2 H2 106.0 . . ? C13 C2 H2 106.0 . . ? C3 C2 H2 106.0 . . ? C4 C3 C12 110.98(17) . . ? C4 C3 C2 115.64(18) . . ? C12 C3 C2 109.29(17) . . ? C4 C3 H3 106.8 . . ? C12 C3 H3 106.8 . . ? C2 C3 H3 106.8 . . ? C5 C4 C3 110.68(18) . . ? C5 C4 H4A 109.5 . . ? C3 C4 H4A 109.5 . . ? C5 C4 H4B 109.5 . . ? C3 C4 H4B 109.5 . . ? H4A C4 H4B 108.1 . . ? C4 C5 C6 112.72(18) . . ? C4 C5 H5A 109.0 . . ? C6 C5 H5A 109.0 . . ? C4 C5 H5B 109.0 . . ? C6 C5 H5B 109.0 . . ? H5A C5 H5B 107.8 . . ? C15 C6 C5 110.79(19) . . ? C15 C6 C7 111.6(2) . . ? C5 C6 C7 111.23(18) . . ? C15 C6 H6 107.7 . . ? C5 C6 H6 107.7 . . ? C7 C6 H6 107.7 . . ? C8 C7 C12 112.42(17) . . ? C8 C7 C6 111.67(18) . . ? C12 C7 C6 111.99(16) . . ? C8 C7 H7 106.8 . . ? C12 C7 H7 106.8 . . ? C6 C7 H7 106.8 . . ? C9 C8 C7 117.12(18) . . ? C9 C8 H8A 108.0 . . ? C7 C8 H8A 108.0 . . ? C9 C8 H8B 108.0 . . ? C7 C8 H8B 108.0 . . ? H8A C8 H8B 107.3 . . ? C10 C9 C8 114.99(17) . . ? C10 C9 H9A 108.5 . . ? C8 C9 H9A 108.5 . . ? C10 C9 H9B 108.5 . . ? C8 C9 H9B 108.5 . . ? H9A C9 H9B 107.5 . . ? O5 C10 O3 107.26(15) . . ? O5 C10 C14 104.34(18) . . ? O3 C10 C14 107.36(18) . . ? O5 C10 C9 112.91(19) . . ? O3 C10 C9 109.62(17) . . ? C14 C10 C9 114.90(18) . . ? O3 C11 O2 105.81(15) . . ? O3 C11 C12 114.37(16) . . ? O2 C11 C12 114.24(16) . . ? O3 C11 H11 107.3 . . ? O2 C11 H11 107.3 . . ? C12 C11 H11 107.3 . . ? O4 C12 C11 111.29(16) . . ? O4 C12 C3 104.83(16) . . ? C11 C12 C3 110.37(16) . . ? O4 C12 C7 106.59(16) . . ? C11 C12 C7 110.86(16) . . ? C3 C12 C7 112.70(16) . . ? C2 C13 H13A 109.5 . . ? C2 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C2 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C10 C14 H14A 109.5 . . ? C10 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C10 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C6 C15 H15A 109.5 . . ? C6 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C6 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? O6 C16 C21 122.0(2) . . ? O6 C16 C17 117.1(2) . . ? C21 C16 C17 120.9(2) . . ? C18 C17 C16 119.2(2) . . ? C18 C17 H17 120.4 . . ? C16 C17 H17 120.4 . . ? O7 C18 C19 122.5(2) . . ? O7 C18 C17 116.7(2) . . ? C19 C18 C17 120.8(2) . . ? C18 C19 C20 118.7(2) . . ? C18 C19 H19 120.6 . . ? C20 C19 H19 120.6 . . ? C19 C20 C21 121.8(2) . . ? C19 C20 H20 119.1 . . ? C21 C20 H20 119.1 . . ? C16 C21 C20 118.6(2) . . ? C16 C21 H21 120.7 . . ? C20 C21 H21 120.7 . . ? O8 C22 O9 117.0(2) . . ? O8 C22 C23 122.7(2) . . ? O9 C22 C23 120.13(17) . . ? C22 C23 C35 110.71(18) . . ? C22 C23 C24 112.84(18) . . ? C35 C23 C24 113.91(18) . . ? C22 C23 H23 106.3 . . ? C35 C23 H23 106.3 . . ? C24 C23 H23 106.3 . . ? C25 C24 C29 111.09(17) . . ? C25 C24 C23 115.17(17) . . ? C29 C24 C23 108.65(16) . . ? C25 C24 H24 107.2 . . ? C29 C24 H24 107.2 . . ? C23 C24 H24 107.2 . . ? C26 C25 C24 110.17(18) . . ? C26 C25 H25A 109.6 . . ? C24 C25 H25A 109.6 . . ? C26 C25 H25B 109.6 . . ? C24 C25 H25B 109.6 . . ? H25A C25 H25B 108.1 . . ? C25 C26 C27 112.94(19) . . ? C25 C26 H26A 109.0 . . ? C27 C26 H26A 109.0 . . ? C25 C26 H26B 109.0 . . ? C27 C26 H26B 109.0 . . ? H26A C26 H26B 107.8 . . ? C26 C27 C34 110.2(2) . . ? C26 C27 C28 111.50(17) . . ? C34 C27 C28 111.87(19) . . ? C26 C27 H27 107.7 . . ? C34 C27 H27 107.7 . . ? C28 C27 H27 107.7 . . ? C33 C28 C27 111.63(17) . . ? C33 C28 C29 112.14(18) . . ? C27 C28 C29 111.51(16) . . ? C33 C28 H28 107.1 . . ? C27 C28 H28 107.1 . . ? C29 C28 H28 107.1 . . ? O10 C29 C30 111.90(16) . . ? O10 C29 C24 104.99(15) . . ? C30 C29 C24 110.80(15) . . ? O10 C29 C28 106.72(15) . . ? C30 C29 C28 109.58(16) . . ? C24 C29 C28 112.75(17) . . ? O11 C30 O9 105.85(16) . . ? O11 C30 C29 114.62(16) . . ? O9 C30 C29 114.23(16) . . ? O11 C30 H30 107.2 . . ? O9 C30 H30 107.2 . . ? C29 C30 H30 107.2 . . ? O12 C31 O11 107.41(15) . . ? O12 C31 C36 105.41(19) . . ? O11 C31 C36 106.59(19) . . ? O12 C31 C32 112.29(19) . . ? O11 C31 C32 110.13(19) . . ? C36 C31 C32 114.56(19) . . ? C33 C32 C31 114.58(18) . . ? C33 C32 H32A 108.6 . . ? C31 C32 H32A 108.6 . . ? C33 C32 H32B 108.6 . . ? C31 C32 H32B 108.6 . . ? H32A C32 H32B 107.6 . . ? C32 C33 C28 116.33(18) . . ? C32 C33 H33A 108.2 . . ? C28 C33 H33A 108.2 . . ? C32 C33 H33B 108.2 . . ? C28 C33 H33B 108.2 . . ? H33A C33 H33B 107.4 . . ? C27 C34 H34A 109.5 . . ? C27 C34 H34B 109.5 . . ? H34A C34 H34B 109.5 . . ? C27 C34 H34C 109.5 . . ? H34A C34 H34C 109.5 . . ? H34B C34 H34C 109.5 . . ? C23 C35 H35A 109.5 . . ? C23 C35 H35B 109.5 . . ? H35A C35 H35B 109.5 . . ? C23 C35 H35C 109.5 . . ? H35A C35 H35C 109.5 . . ? H35B C35 H35C 109.5 . . ? C31 C36 H36A 109.5 . . ? C31 C36 H36B 109.5 . . ? H36A C36 H36B 109.5 . . ? C31 C36 H36C 109.5 . . ? H36A C36 H36C 109.5 . . ? H36B C36 H36C 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 C12 O4 O5 C10 48.74(19) . . . . ? C29 O10 O12 C31 48.42(18) . . . . ? C11 O2 C1 O1 178.2(2) . . . . ? C11 O2 C1 C2 -5.2(3) . . . . ? O1 C1 C2 C13 -35.1(3) . . . . ? O2 C1 C2 C13 148.4(2) . . . . ? O1 C1 C2 C3 -164.4(2) . . . . ? O2 C1 C2 C3 19.1(3) . . . . ? C1 C2 C3 C4 80.7(2) . . . . ? C13 C2 C3 C4 -46.7(3) . . . . ? C1 C2 C3 C12 -45.3(2) . . . . ? C13 C2 C3 C12 -172.8(2) . . . . ? C12 C3 C4 C5 -56.3(2) . . . . ? C2 C3 C4 C5 178.46(18) . . . . ? C3 C4 C5 C6 57.1(3) . . . . ? C4 C5 C6 C15 -178.7(2) . . . . ? C4 C5 C6 C7 -54.0(3) . . . . ? C15 C6 C7 C8 -58.2(2) . . . . ? C5 C6 C7 C8 177.57(18) . . . . ? C15 C6 C7 C12 174.75(19) . . . . ? C5 C6 C7 C12 50.5(2) . . . . ? C12 C7 C8 C9 -33.6(3) . . . . ? C6 C7 C8 C9 -160.46(18) . . . . ? C7 C8 C9 C10 54.4(3) . . . . ? O4 O5 C10 O3 -75.46(19) . . . . ? O4 O5 C10 C14 170.85(16) . . . . ? O4 O5 C10 C9 45.4(2) . . . . ? C11 O3 C10 O5 34.5(2) . . . . ? C11 O3 C10 C14 146.10(17) . . . . ? C11 O3 C10 C9 -88.5(2) . . . . ? C8 C9 C10 O5 -93.3(2) . . . . ? C8 C9 C10 O3 26.2(2) . . . . ? C8 C9 C10 C14 147.2(2) . . . . ? C10 O3 C11 O2 -99.92(18) . . . . ? C10 O3 C11 C12 26.7(2) . . . . ? C1 O2 C11 O3 145.60(19) . . . . ? C1 O2 C11 C12 18.9(3) . . . . ? O5 O4 C12 C11 11.9(2) . . . . ? O5 O4 C12 C3 131.18(15) . . . . ? O5 O4 C12 C7 -109.12(16) . . . . ? O3 C11 C12 O4 -51.7(2) . . . . ? O2 C11 C12 O4 70.4(2) . . . . ? O3 C11 C12 C3 -167.69(16) . . . . ? O2 C11 C12 C3 -45.6(2) . . . . ? O3 C11 C12 C7 66.7(2) . . . . ? O2 C11 C12 C7 -171.15(16) . . . . ? C4 C3 C12 O4 169.84(16) . . . . ? C2 C3 C12 O4 -61.5(2) . . . . ? C4 C3 C12 C11 -70.2(2) . . . . ? C2 C3 C12 C11 58.5(2) . . . . ? C4 C3 C12 C7 54.3(2) . . . . ? C2 C3 C12 C7 -176.99(17) . . . . ? C8 C7 C12 O4 67.4(2) . . . . ? C6 C7 C12 O4 -165.93(16) . . . . ? C8 C7 C12 C11 -53.9(2) . . . . ? C6 C7 C12 C11 72.8(2) . . . . ? C8 C7 C12 C3 -178.16(17) . . . . ? C6 C7 C12 C3 -51.5(2) . . . . ? O6 C16 C17 C18 179.5(2) . . . . ? C21 C16 C17 C18 1.2(3) . . . . ? C16 C17 C18 O7 178.0(2) . . . . ? C16 C17 C18 C19 -0.9(3) . . . . ? O7 C18 C19 C20 -179.0(2) . . . . ? C17 C18 C19 C20 -0.1(4) . . . . ? C18 C19 C20 C21 0.8(4) . . . . ? O6 C16 C21 C20 -178.6(3) . . . . ? C17 C16 C21 C20 -0.4(4) . . . . ? C19 C20 C21 C16 -0.6(4) . . . . ? C30 O9 C22 O8 172.6(2) . . . . ? C30 O9 C22 C23 -11.3(4) . . . . ? O8 C22 C23 C35 -28.1(4) . . . . ? O9 C22 C23 C35 156.0(2) . . . . ? O8 C22 C23 C24 -157.1(3) . . . . ? O9 C22 C23 C24 27.0(3) . . . . ? C22 C23 C24 C25 75.0(2) . . . . ? C35 C23 C24 C25 -52.3(3) . . . . ? C22 C23 C24 C29 -50.3(2) . . . . ? C35 C23 C24 C29 -177.61(18) . . . . ? C29 C24 C25 C26 -56.6(2) . . . . ? C23 C24 C25 C26 179.30(18) . . . . ? C24 C25 C26 C27 57.4(2) . . . . ? C25 C26 C27 C34 -179.3(2) . . . . ? C25 C26 C27 C28 -54.5(2) . . . . ? C26 C27 C28 C33 176.55(18) . . . . ? C34 C27 C28 C33 -59.6(2) . . . . ? C26 C27 C28 C29 50.2(2) . . . . ? C34 C27 C28 C29 174.1(2) . . . . ? O12 O10 C29 C30 11.0(2) . . . . ? O12 O10 C29 C24 131.24(14) . . . . ? O12 O10 C29 C28 -108.87(16) . . . . ? C25 C24 C29 O10 170.40(16) . . . . ? C23 C24 C29 O10 -61.9(2) . . . . ? C25 C24 C29 C30 -68.6(2) . . . . ? C23 C24 C29 C30 59.1(2) . . . . ? C25 C24 C29 C28 54.6(2) . . . . ? C23 C24 C29 C28 -177.72(16) . . . . ? C33 C28 C29 O10 68.0(2) . . . . ? C27 C28 C29 O10 -165.97(16) . . . . ? C33 C28 C29 C30 -53.3(2) . . . . ? C27 C28 C29 C30 72.7(2) . . . . ? C33 C28 C29 C24 -177.24(16) . . . . ? C27 C28 C29 C24 -51.2(2) . . . . ? C31 O11 C30 O9 -102.82(19) . . . . ? C31 O11 C30 C29 24.0(2) . . . . ? C22 O9 C30 O11 146.8(2) . . . . ? C22 O9 C30 C29 19.8(3) . . . . ? O10 C29 C30 O11 -49.4(2) . . . . ? C24 C29 C30 O11 -166.22(17) . . . . ? C28 C29 C30 O11 68.7(2) . . . . ? O10 C29 C30 O9 73.0(2) . . . . ? C24 C29 C30 O9 -43.8(2) . . . . ? C28 C29 C30 O9 -168.86(17) . . . . ? O10 O12 C31 O11 -75.72(19) . . . . ? O10 O12 C31 C36 170.89(17) . . . . ? O10 O12 C31 C32 45.5(2) . . . . ? C30 O11 C31 O12 36.5(2) . . . . ? C30 O11 C31 C36 149.04(18) . . . . ? C30 O11 C31 C32 -86.1(2) . . . . ? O12 C31 C32 C33 -95.5(2) . . . . ? O11 C31 C32 C33 24.2(3) . . . . ? C36 C31 C32 C33 144.3(2) . . . . ? C31 C32 C33 C28 57.4(3) . . . . ? C27 C28 C33 C32 -161.44(19) . . . . ? C29 C28 C33 C32 -35.5(3) . . . . ? _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 27.90 _diffrn_measured_fraction_theta_full 0.985 _refine_diff_density_max 0.268 _refine_diff_density_min -0.226 _refine_diff_density_rms 0.038 data_art-orc _database_code_depnum_ccdc_archive 'CCDC 735602' _audit_creation_method SHELXL-97 _chemical_name_systematic ; artemisinin-orcinol 1/1 ; _chemical_name_common 'artemisinin-orcinol 1/1' _chemical_melting_point ? _chemical_formula_moiety 'C15 H22 O5, C7 H8 O2' _chemical_formula_sum 'C22 H30 O7' _chemical_formula_weight 406.46 _chemical_absolute_configuration ; 3626 Friedel pairs were averaged for the refinement ; 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 orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 9.0658(1) _cell_length_b 14.1061(3) _cell_length_c 16.5554(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2117.16(6) _cell_formula_units_Z 4 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 17422 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 33.73 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.275 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 872 _exptl_absorpt_coefficient_mu 0.094 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.920 _exptl_absorpt_correction_T_max 0.983 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; The -OH hydrogen atoms were located and their positions were refined satisfactorily. ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method 'Thin slice \w and \f scans' _diffrn_reflns_number 22329 _diffrn_reflns_av_R_equivalents 0.0356 _diffrn_reflns_av_sigmaI/netI 0.0384 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 3.63 _diffrn_reflns_theta_max 33.72 _reflns_number_total 4677 _reflns_number_gt 3587 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V. 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor 1997) ; _computing_structure_solution 'SIR-92 (Altomare et al. 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick 1997)' _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^)+(0.0591P)^2^+0.2789P] 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 0.0(9) _refine_ls_number_reflns 4677 _refine_ls_number_parameters 273 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0723 _refine_ls_R_factor_gt 0.0475 _refine_ls_wR_factor_ref 0.1205 _refine_ls_wR_factor_gt 0.1076 _refine_ls_goodness_of_fit_ref 1.032 _refine_ls_restrained_S_all 1.032 _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 O1 O 0.91282(14) 0.38435(9) 0.51849(8) 0.0308(3) Uani 1 1 d . . . O2 O 0.86713(15) 0.23441(9) 0.47554(7) 0.0294(3) Uani 1 1 d . . . O3 O 0.66126(14) 0.36910(9) 0.53423(8) 0.0304(3) Uani 1 1 d . . . O4 O 0.66908(13) 0.30737(9) 0.60591(7) 0.0288(3) Uani 1 1 d . . . O5 O 0.79123(18) 0.10342(11) 0.42008(8) 0.0399(3) Uani 1 1 d . . . O6 O 0.41552(18) 0.37656(9) 0.72781(8) 0.0357(3) Uani 1 1 d D . . H6A H 0.388(3) 0.3698(18) 0.6783(14) 0.043 Uiso 1 1 d D . . O7 O 0.4453(2) 0.04024(10) 0.71776(9) 0.0413(4) Uani 1 1 d D . . H7A H 0.490(3) -0.0078(18) 0.7385(16) 0.050 Uiso 1 1 d D . . C1 C 0.91278(18) 0.29075(12) 0.54468(10) 0.0255(3) Uani 1 1 d . . . H1 H 1.0168 0.2731 0.5580 0.031 Uiso 1 1 calc R . . C2 C 0.7787(2) 0.43471(12) 0.53829(11) 0.0301(3) Uani 1 1 d . . . C3 C 0.7928(3) 0.48044(14) 0.62164(13) 0.0390(4) Uani 1 1 d . . . H3A H 0.8217 0.5476 0.6145 0.047 Uiso 1 1 calc R . . H3B H 0.6948 0.4796 0.6481 0.047 Uiso 1 1 calc R . . C4 C 0.9040(3) 0.43274(14) 0.67767(13) 0.0400(5) Uani 1 1 d . . . H4A H 0.9029 0.4666 0.7301 0.048 Uiso 1 1 calc R . . H4B H 1.0036 0.4408 0.6541 0.048 Uiso 1 1 calc R . . C5 C 0.8794(2) 0.32637(13) 0.69409(10) 0.0304(4) Uani 1 1 d . . . H5 H 0.8016 0.3219 0.7368 0.036 Uiso 1 1 calc R . . C6 C 0.81952(18) 0.27356(12) 0.61956(9) 0.0241(3) Uani 1 1 d . . . C7 C 0.80399(19) 0.16660(12) 0.63497(10) 0.0248(3) Uani 1 1 d . . . H7 H 0.7325 0.1587 0.6805 0.030 Uiso 1 1 calc R . . C8 C 0.73601(19) 0.11850(12) 0.56079(10) 0.0265(3) Uani 1 1 d . . . H8 H 0.6312 0.1405 0.5590 0.032 Uiso 1 1 calc R . . C9 C 0.80279(19) 0.14934(12) 0.48200(10) 0.0275(3) Uani 1 1 d . . . C10 C 1.0197(2) 0.28040(14) 0.72935(11) 0.0339(4) Uani 1 1 d . . . H10 H 1.1019 0.2912 0.6901 0.041 Uiso 1 1 calc R . . C11 C 1.0020(2) 0.17382(14) 0.74029(12) 0.0357(4) Uani 1 1 d . . . H11A H 0.9294 0.1616 0.7837 0.043 Uiso 1 1 calc R . . H11B H 1.0976 0.1464 0.7574 0.043 Uiso 1 1 calc R . . C12 C 0.9510(2) 0.12498(13) 0.66300(11) 0.0306(3) Uani 1 1 d . . . H12A H 0.9396 0.0562 0.6729 0.037 Uiso 1 1 calc R . . H12B H 1.0262 0.1336 0.6202 0.037 Uiso 1 1 calc R . . C13 C 0.7284(3) 0.01057(13) 0.56635(13) 0.0391(4) Uani 1 1 d . . . H13A H 0.6674 -0.0140 0.5222 0.059 Uiso 1 1 calc R . . H13B H 0.6849 -0.0077 0.6182 0.059 Uiso 1 1 calc R . . H13C H 0.8281 -0.0158 0.5622 0.059 Uiso 1 1 calc R . . C14 C 1.0638(3) 0.32634(19) 0.80986(14) 0.0520(6) Uani 1 1 d . . . H14A H 1.1462 0.2911 0.8336 0.078 Uiso 1 1 calc R . . H14B H 0.9796 0.3251 0.8469 0.078 Uiso 1 1 calc R . . H14C H 1.0938 0.3922 0.8004 0.078 Uiso 1 1 calc R . . C15 C 0.7513(3) 0.50453(15) 0.47041(14) 0.0406(4) Uani 1 1 d . . . H15A H 0.7353 0.4699 0.4199 0.061 Uiso 1 1 calc R . . H15B H 0.8370 0.5463 0.4646 0.061 Uiso 1 1 calc R . . H15C H 0.6637 0.5426 0.4829 0.061 Uiso 1 1 calc R . . C16 C 0.4566(2) 0.29111(12) 0.76038(10) 0.0290(3) Uani 1 1 d . . . C17 C 0.5301(3) 0.29370(14) 0.83407(12) 0.0414(5) Uani 1 1 d . . . H17 H 0.5479 0.3526 0.8602 0.050 Uiso 1 1 calc R . . C18 C 0.5776(3) 0.20954(15) 0.86934(12) 0.0462(5) Uani 1 1 d . . . C19 C 0.5509(2) 0.12350(14) 0.83130(12) 0.0360(4) Uani 1 1 d . . . H19 H 0.5842 0.0660 0.8549 0.043 Uiso 1 1 calc R . . C20 C 0.4750(2) 0.12239(12) 0.75834(10) 0.0289(3) Uani 1 1 d . . . C21 C 0.4276(2) 0.20591(12) 0.72226(10) 0.0284(3) Uani 1 1 d . . . H21 H 0.3762 0.2045 0.6723 0.034 Uiso 1 1 calc R . . C22 C 0.6602(5) 0.2119(2) 0.94884(17) 0.0890(14) Uani 1 1 d . . . H22A H 0.6936 0.1478 0.9625 0.134 Uiso 1 1 calc R . . H22B H 0.5947 0.2355 0.9914 0.134 Uiso 1 1 calc R . . H22C H 0.7457 0.2540 0.9440 0.134 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 0.0284(6) 0.0240(5) 0.0401(6) 0.0047(5) 0.0062(5) -0.0016(5) O2 0.0370(7) 0.0273(6) 0.0237(5) 0.0006(5) 0.0052(5) -0.0001(5) O3 0.0271(6) 0.0294(6) 0.0348(6) 0.0092(5) -0.0016(5) 0.0017(5) O4 0.0239(6) 0.0314(6) 0.0312(6) 0.0079(5) 0.0039(5) 0.0037(5) O5 0.0503(8) 0.0405(7) 0.0290(6) -0.0062(6) 0.0006(6) -0.0063(7) O6 0.0548(8) 0.0218(5) 0.0306(6) 0.0018(5) -0.0064(6) 0.0023(6) O7 0.0652(10) 0.0234(6) 0.0352(7) -0.0025(5) -0.0050(7) 0.0016(7) C1 0.0242(7) 0.0242(7) 0.0280(7) 0.0009(6) 0.0024(6) -0.0005(6) C2 0.0290(8) 0.0231(7) 0.0382(9) 0.0017(7) 0.0006(7) 0.0015(6) C3 0.0466(11) 0.0261(8) 0.0444(10) -0.0045(8) -0.0007(9) 0.0067(8) C4 0.0501(12) 0.0294(9) 0.0405(10) -0.0073(8) -0.0082(9) 0.0011(9) C5 0.0354(9) 0.0288(8) 0.0269(7) -0.0035(7) -0.0017(7) 0.0016(7) C6 0.0213(7) 0.0256(7) 0.0253(7) 0.0005(6) 0.0014(5) 0.0021(6) C7 0.0255(7) 0.0243(7) 0.0246(7) 0.0026(6) 0.0008(6) -0.0002(6) C8 0.0267(7) 0.0257(7) 0.0272(7) 0.0017(6) -0.0010(6) -0.0016(6) C9 0.0266(8) 0.0295(8) 0.0265(7) 0.0007(6) -0.0008(6) 0.0026(6) C10 0.0355(9) 0.0354(9) 0.0307(8) -0.0028(7) -0.0082(7) -0.0020(8) C11 0.0392(10) 0.0347(9) 0.0331(9) 0.0032(8) -0.0095(7) -0.0008(8) C12 0.0342(9) 0.0264(7) 0.0313(8) 0.0014(7) -0.0059(7) 0.0023(7) C13 0.0524(12) 0.0245(8) 0.0404(10) 0.0022(7) -0.0059(9) -0.0053(8) C14 0.0639(16) 0.0494(12) 0.0428(11) -0.0082(10) -0.0210(11) -0.0013(12) C15 0.0441(11) 0.0289(8) 0.0488(11) 0.0106(8) -0.0016(9) 0.0003(8) C16 0.0374(9) 0.0226(7) 0.0271(7) 0.0034(6) 0.0017(7) -0.0014(7) C17 0.0687(14) 0.0228(8) 0.0328(9) 0.0012(7) -0.0121(9) -0.0066(9) C18 0.0730(16) 0.0293(9) 0.0364(9) 0.0067(8) -0.0178(10) -0.0076(11) C19 0.0494(11) 0.0256(8) 0.0329(8) 0.0064(7) -0.0041(8) -0.0038(8) C20 0.0364(9) 0.0230(7) 0.0274(7) 0.0006(6) 0.0062(7) -0.0022(7) C21 0.0355(9) 0.0252(7) 0.0244(7) 0.0006(6) 0.0020(6) -0.0007(7) C22 0.165(4) 0.0388(13) 0.0631(16) 0.0096(12) -0.068(2) -0.0131(18) _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 C1 1.390(2) . ? O1 C2 1.446(2) . ? O2 C9 1.339(2) . ? O2 C1 1.454(2) . ? O3 C2 1.412(2) . ? O3 O4 1.4736(16) . ? O4 C6 1.462(2) . ? O5 C9 1.217(2) . ? O6 C16 1.372(2) . ? O6 H6A 0.86(2) . ? O7 C20 1.366(2) . ? O7 H7A 0.86(2) . ? C1 C6 1.520(2) . ? C1 H1 1.0000 . ? C2 C15 1.515(3) . ? C2 C3 1.528(3) . ? C3 C4 1.527(3) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 C5 1.541(3) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C6 1.540(2) . ? C5 C10 1.543(3) . ? C5 H5 1.0000 . ? C6 C7 1.537(2) . ? C7 C12 1.529(2) . ? C7 C8 1.532(2) . ? C7 H7 1.0000 . ? C8 C9 1.502(2) . ? C8 C13 1.527(2) . ? C8 H8 1.0000 . ? C10 C11 1.523(3) . ? C10 C14 1.535(3) . ? C10 H10 1.0000 . ? C11 C12 1.525(3) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 C21 1.383(2) . ? C16 C17 1.391(3) . ? C17 C18 1.391(3) . ? C17 H17 0.9500 . ? C18 C19 1.389(3) . ? C18 C22 1.515(3) . ? C19 C20 1.390(3) . ? C19 H19 0.9500 . ? C20 C21 1.389(2) . ? C21 H21 0.9500 . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? 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 C1 O1 C2 113.32(13) . . ? C9 O2 C1 123.45(13) . . ? C2 O3 O4 108.22(12) . . ? C6 O4 O3 111.23(11) . . ? C16 O6 H6A 110.9(17) . . ? C20 O7 H7A 112.3(19) . . ? O1 C1 O2 105.89(13) . . ? O1 C1 C6 113.96(14) . . ? O2 C1 C6 113.37(13) . . ? O1 C1 H1 107.8 . . ? O2 C1 H1 107.8 . . ? C6 C1 H1 107.8 . . ? O3 C2 O1 107.53(13) . . ? O3 C2 C15 105.48(16) . . ? O1 C2 C15 106.82(16) . . ? O3 C2 C3 112.48(16) . . ? O1 C2 C3 109.99(16) . . ? C15 C2 C3 114.15(16) . . ? C4 C3 C2 114.68(16) . . ? C4 C3 H3A 108.6 . . ? C2 C3 H3A 108.6 . . ? C4 C3 H3B 108.6 . . ? C2 C3 H3B 108.6 . . ? H3A C3 H3B 107.6 . . ? C3 C4 C5 116.14(18) . . ? C3 C4 H4A 108.3 . . ? C5 C4 H4A 108.3 . . ? C3 C4 H4B 108.3 . . ? C5 C4 H4B 108.3 . . ? H4A C4 H4B 107.4 . . ? C6 C5 C4 112.38(15) . . ? C6 C5 C10 112.97(15) . . ? C4 C5 C10 110.88(17) . . ? C6 C5 H5 106.7 . . ? C4 C5 H5 106.7 . . ? C10 C5 H5 106.7 . . ? O4 C6 C1 109.91(13) . . ? O4 C6 C7 105.09(13) . . ? C1 C6 C7 110.06(13) . . ? O4 C6 C5 107.13(13) . . ? C1 C6 C5 112.35(14) . . ? C7 C6 C5 111.98(13) . . ? C12 C7 C8 115.08(14) . . ? C12 C7 C6 110.34(15) . . ? C8 C7 C6 109.79(13) . . ? C12 C7 H7 107.1 . . ? C8 C7 H7 107.1 . . ? C6 C7 H7 107.1 . . ? C9 C8 C13 111.05(15) . . ? C9 C8 C7 113.92(14) . . ? C13 C8 C7 114.29(15) . . ? C9 C8 H8 105.5 . . ? C13 C8 H8 105.5 . . ? C7 C8 H8 105.5 . . ? O5 C9 O2 116.57(16) . . ? O5 C9 C8 122.85(16) . . ? O2 C9 C8 120.30(15) . . ? C11 C10 C14 109.93(17) . . ? C11 C10 C5 111.92(16) . . ? C14 C10 C5 111.46(17) . . ? C11 C10 H10 107.8 . . ? C14 C10 H10 107.8 . . ? C5 C10 H10 107.8 . . ? C10 C11 C12 112.22(16) . . ? C10 C11 H11A 109.2 . . ? C12 C11 H11A 109.2 . . ? C10 C11 H11B 109.2 . . ? C12 C11 H11B 109.2 . . ? H11A C11 H11B 107.9 . . ? C11 C12 C7 110.23(16) . . ? C11 C12 H12A 109.6 . . ? C7 C12 H12A 109.6 . . ? C11 C12 H12B 109.6 . . ? C7 C12 H12B 109.6 . . ? H12A C12 H12B 108.1 . . ? C8 C13 H13A 109.5 . . ? C8 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C8 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C10 C14 H14A 109.5 . . ? C10 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C10 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C2 C15 H15A 109.5 . . ? C2 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C2 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? O6 C16 C21 122.19(16) . . ? O6 C16 C17 116.85(16) . . ? C21 C16 C17 120.95(16) . . ? C16 C17 C18 119.61(17) . . ? C16 C17 H17 120.2 . . ? C18 C17 H17 120.2 . . ? C19 C18 C17 120.09(18) . . ? C19 C18 C22 120.0(2) . . ? C17 C18 C22 119.9(2) . . ? C18 C19 C20 119.36(18) . . ? C18 C19 H19 120.3 . . ? C20 C19 H19 120.3 . . ? O7 C20 C21 116.54(16) . . ? O7 C20 C19 122.30(17) . . ? C21 C20 C19 121.15(17) . . ? C16 C21 C20 118.82(16) . . ? C16 C21 H21 120.6 . . ? C20 C21 H21 120.6 . . ? C18 C22 H22A 109.5 . . ? C18 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C18 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 C2 O3 O4 C6 -46.46(16) . . . . ? C2 O1 C1 O2 96.45(16) . . . . ? C2 O1 C1 C6 -28.8(2) . . . . ? C9 O2 C1 O1 -154.76(15) . . . . ? C9 O2 C1 C6 -29.1(2) . . . . ? O4 O3 C2 O1 74.47(16) . . . . ? O4 O3 C2 C15 -171.80(14) . . . . ? O4 O3 C2 C3 -46.77(17) . . . . ? C1 O1 C2 O3 -33.85(19) . . . . ? C1 O1 C2 C15 -146.68(16) . . . . ? C1 O1 C2 C3 88.94(18) . . . . ? O3 C2 C3 C4 95.4(2) . . . . ? O1 C2 C3 C4 -24.5(2) . . . . ? C15 C2 C3 C4 -144.50(19) . . . . ? C2 C3 C4 C5 -56.7(3) . . . . ? C3 C4 C5 C6 35.7(3) . . . . ? C3 C4 C5 C10 163.21(18) . . . . ? O3 O4 C6 C1 -14.73(17) . . . . ? O3 O4 C6 C7 -133.12(12) . . . . ? O3 O4 C6 C5 107.61(14) . . . . ? O1 C1 C6 O4 54.73(18) . . . . ? O2 C1 C6 O4 -66.51(17) . . . . ? O1 C1 C6 C7 170.01(14) . . . . ? O2 C1 C6 C7 48.78(18) . . . . ? O1 C1 C6 C5 -64.47(18) . . . . ? O2 C1 C6 C5 174.30(14) . . . . ? C4 C5 C6 O4 -68.65(19) . . . . ? C10 C5 C6 O4 164.97(14) . . . . ? C4 C5 C6 C1 52.2(2) . . . . ? C10 C5 C6 C1 -74.22(19) . . . . ? C4 C5 C6 C7 176.62(16) . . . . ? C10 C5 C6 C7 50.2(2) . . . . ? O4 C6 C7 C12 -171.29(13) . . . . ? C1 C6 C7 C12 70.41(17) . . . . ? C5 C6 C7 C12 -55.32(18) . . . . ? O4 C6 C7 C8 60.84(16) . . . . ? C1 C6 C7 C8 -57.46(18) . . . . ? C5 C6 C7 C8 176.81(14) . . . . ? C12 C7 C8 C9 -79.67(19) . . . . ? C6 C7 C8 C9 45.52(19) . . . . ? C12 C7 C8 C13 49.5(2) . . . . ? C6 C7 C8 C13 174.67(16) . . . . ? C1 O2 C9 O5 -168.84(16) . . . . ? C1 O2 C9 C8 17.0(2) . . . . ? C13 C8 C9 O5 30.1(3) . . . . ? C7 C8 C9 O5 160.81(17) . . . . ? C13 C8 C9 O2 -156.19(16) . . . . ? C7 C8 C9 O2 -25.4(2) . . . . ? C6 C5 C10 C11 -48.6(2) . . . . ? C4 C5 C10 C11 -175.76(16) . . . . ? C6 C5 C10 C14 -172.15(17) . . . . ? C4 C5 C10 C14 60.7(2) . . . . ? C14 C10 C11 C12 177.26(19) . . . . ? C5 C10 C11 C12 52.8(2) . . . . ? C10 C11 C12 C7 -58.5(2) . . . . ? C8 C7 C12 C11 -176.03(15) . . . . ? C6 C7 C12 C11 59.06(19) . . . . ? O6 C16 C17 C18 -178.6(2) . . . . ? C21 C16 C17 C18 1.1(3) . . . . ? C16 C17 C18 C19 -0.3(4) . . . . ? C16 C17 C18 C22 178.9(3) . . . . ? C17 C18 C19 C20 -0.7(4) . . . . ? C22 C18 C19 C20 -180.0(3) . . . . ? C18 C19 C20 O7 179.9(2) . . . . ? C18 C19 C20 C21 1.0(3) . . . . ? O6 C16 C21 C20 178.84(18) . . . . ? C17 C16 C21 C20 -0.8(3) . . . . ? O7 C20 C21 C16 -179.21(18) . . . . ? C19 C20 C21 C16 -0.3(3) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 33.72 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.253 _refine_diff_density_min -0.190 _refine_diff_density_rms 0.043