#------------------------------------------------------------------------------ #$Date: 2019-12-21 02:10:36 +0200 (Sat, 21 Dec 2019) $ #$Revision: 245458 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/55/67/1556700.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_1556700 loop_ _publ_author_name 'Varela, Kaitlyn' 'Arman, Hadi D.' 'Yoshimoto, Francis K.' _publ_section_title ; Synthesis of [3,3-2H2]-Dihydroartemisinic Acid to Measure the Rate of Nonenzymatic Conversion of Dihydroartemisinic Acid to Artemisinin ; _journal_name_full 'Journal of Natural Products' _journal_paper_doi 10.1021/acs.jnatprod.9b00686 _journal_year 2019 _chemical_absolute_configuration unk _chemical_formula_moiety 'C15 H26 O2' _chemical_formula_sum 'C15 H26 O2' _chemical_formula_weight 238.36 _space_group_crystal_system orthorhombic _space_group_IT_number 19 _space_group_name_Hall 'P 2ac 2ab' _space_group_name_H-M_alt 'P 21 21 21' _atom_sites_solution_hydrogens mixed _atom_sites_solution_primary dual _audit_creation_date 2019-05-03 _audit_creation_method ; Olex2 1.2 (compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) ; _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 7.6289(2) _cell_length_b 13.0886(3) _cell_length_c 14.6321(3) _cell_measurement_reflns_used 9099 _cell_measurement_temperature 98(2) _cell_measurement_theta_max 29.4000 _cell_measurement_theta_min 3.0180 _cell_volume 1461.04(6) _computing_cell_refinement 'CrysAlisPro 1.171.40.43a (Rigaku OD, 2019)' _computing_data_collection 'CrysAlisPro 1.171.40.43a (Rigaku OD, 2019)' _computing_data_reduction 'CrysAlisPro 1.171.40.43a (Rigaku OD, 2019)' _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'ShelXL (Sheldrick, 2015)' _computing_structure_solution 'ShelXT (Sheldrick, 2015)' _diffrn_ambient_temperature 98(2) _diffrn_detector 'CCD plate' _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.991 _diffrn_measurement_details ; List of Runs (angles in degrees, time in seconds): # Type Start End Width t~exp~ \w \q \k \f Frames -------------------------------------------------------------------------- 1 \w -96.00 44.00 1.00 25.00 -- -7.50 -12.00 120.00 140 2 \w -96.00 21.00 1.00 25.00 -- -7.50 -57.00 -60.00 117 3 \w -96.00 9.00 1.00 25.00 -- -7.50 -38.00 -60.00 105 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'XtaLAB AFC12 (RCD3): Kappa single' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_type 'CrysAlisPro convention (1999,Acta A55,543-557)' _diffrn_orient_matrix_UB_11 -0.0151328000 _diffrn_orient_matrix_UB_12 0.0080311000 _diffrn_orient_matrix_UB_13 -0.0472895000 _diffrn_orient_matrix_UB_21 -0.0912822000 _diffrn_orient_matrix_UB_22 0.0039016000 _diffrn_orient_matrix_UB_23 0.0084635000 _diffrn_orient_matrix_UB_31 0.0089761000 _diffrn_orient_matrix_UB_32 0.0534632000 _diffrn_orient_matrix_UB_33 0.0064503000 _diffrn_radiation_monochromator mirror _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0287 _diffrn_reflns_av_unetI/netI 0.0243 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.991 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_number 16694 _diffrn_reflns_point_group_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 0.986 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 27.498 _diffrn_reflns_theta_min 2.784 _diffrn_source 'Rotating-anode X-ray tube' _diffrn_source_type 'Rigaku (Mo) X-ray Source' _exptl_absorpt_coefficient_mu 0.069 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.96351 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.40.43a (Rigaku Oxford Diffraction, 2019) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour 'clear colourless' _exptl_crystal_colour_lustre clear _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.084 _exptl_crystal_description plate _exptl_crystal_F_000 528 _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.17 _refine_diff_density_max 0.357 _refine_diff_density_min -0.170 _refine_diff_density_rms 0.040 _refine_ls_abs_structure_details ; Flack x determined using 1273 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack -0.2(3) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.087 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 163 _refine_ls_number_reflns 3306 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.087 _refine_ls_R_factor_all 0.0401 _refine_ls_R_factor_gt 0.0393 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0418P)^2^+0.4000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0913 _refine_ls_wR_factor_ref 0.0918 _reflns_Friedel_coverage 0.728 _reflns_Friedel_fraction_full 1.000 _reflns_Friedel_fraction_max 0.979 _reflns_number_gt 3263 _reflns_number_total 3306 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file np9b00686_si_002.cif _cod_data_source_block cd1863 _cod_database_code 1556700 _shelx_shelxl_version_number 2016/6 _chemical_oxdiff_formula O2C16 _chemical_oxdiff_usercomment FYV-0571 _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; _shelx_estimated_absorpt_t_max 0.988 _shelx_estimated_absorpt_t_min 0.979 _reflns_odcompleteness_completeness 99.77 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 26.32 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups At 1.5 times of: All C(H,H,H) groups, All C(H,H,H,H,H) groups 2.a Ternary CH refined with riding coordinates: C5(H5), C7(H7), C2(H2A), C1(H1A), C8(H8), C11(H11) 2.b Secondary CH2 refined with riding coordinates: C6(H6A,H6B), C10(H10A,H10B), C9(H9A,H9B), C12(H12A,H12B) 2.c Aromatic/amide H refined with riding coordinates: C3(H3) 2.d Idealised Me refined as rotating group: C13(H13A,H13B,H13C), C15(H15A,H15B,H15C), C14(H14A,H14B,H14C) ; _olex2_exptl_crystal_mounting_method 'nylon loop' _olex2_submission_special_instructions 'No special instructions were received' _oxdiff_exptl_absorpt_empirical_details ; Empirical correction (ABSPACK) includes: - Absorption correction using spherical harmonics - Frame scaling ; _oxdiff_exptl_absorpt_empirical_full_max 1.052 _oxdiff_exptl_absorpt_empirical_full_min 0.967 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' 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_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn O1 O 0.35063(18) 0.32438(11) 0.92458(8) 0.0186(3) Uani 1 1 d . O2 O 0.81042(18) 0.68040(9) 0.47470(9) 0.0167(3) Uani 1 1 d . C6 C 0.5695(2) 0.56382(13) 0.47606(11) 0.0141(4) Uani 1 1 d . H6A H 0.553176 0.559999 0.409026 0.017 Uiso 1 1 calc R H6B H 0.504938 0.624388 0.498591 0.017 Uiso 1 1 calc R C3 C 0.6913(2) 0.50879(13) 0.65147(11) 0.0142(3) Uani 1 1 d . H3 H 0.727744 0.493833 0.712097 0.017 Uiso 1 1 calc R C5 C 0.7633(2) 0.57649(13) 0.49714(11) 0.0131(4) Uani 1 1 d . H5 H 0.831319 0.529343 0.456705 0.016 Uiso 1 1 calc R C7 C 0.4932(2) 0.46738(13) 0.52036(11) 0.0127(3) Uani 1 1 d . H7 H 0.366424 0.463110 0.503487 0.015 Uiso 1 1 calc R C4 C 0.8080(2) 0.55224(13) 0.59579(11) 0.0146(4) Uani 1 1 d . C2 C 0.5053(2) 0.48157(12) 0.62515(11) 0.0122(3) Uani 1 1 d . H2A H 0.429781 0.541325 0.641412 0.015 Uiso 1 1 calc R C1 C 0.4324(2) 0.38794(13) 0.67721(11) 0.0129(3) Uani 1 1 d . H1A H 0.306449 0.380758 0.659357 0.016 Uiso 1 1 calc R C8 C 0.5832(2) 0.36793(13) 0.48861(12) 0.0147(4) Uani 1 1 d . H8 H 0.711129 0.373405 0.502676 0.018 Uiso 1 1 calc R C11 C 0.4370(2) 0.39961(13) 0.78242(12) 0.0139(4) Uani 1 1 d . H11 H 0.560597 0.388648 0.803017 0.017 Uiso 1 1 calc R C10 C 0.5266(3) 0.29076(13) 0.64488(12) 0.0180(4) Uani 1 1 d . H10A H 0.652237 0.294971 0.661388 0.022 Uiso 1 1 calc R H10B H 0.475886 0.230668 0.676322 0.022 Uiso 1 1 calc R C13 C 0.3794(3) 0.50559(14) 0.81491(12) 0.0189(4) Uani 1 1 d . H13A H 0.465911 0.556536 0.795562 0.028 Uiso 1 1 calc GR H13B H 0.370287 0.505868 0.881713 0.028 Uiso 1 1 calc GR H13C H 0.265057 0.522227 0.788237 0.028 Uiso 1 1 calc GR C9 C 0.5092(3) 0.27696(13) 0.54158(12) 0.0185(4) Uani 1 1 d . H9A H 0.383961 0.268172 0.525779 0.022 Uiso 1 1 calc R H9B H 0.572119 0.214151 0.522961 0.022 Uiso 1 1 calc R C12 C 0.3225(3) 0.31857(14) 0.82816(11) 0.0178(4) Uani 1 1 d . H12A H 0.197503 0.331093 0.813913 0.021 Uiso 1 1 calc R H12B H 0.354365 0.249797 0.805404 0.021 Uiso 1 1 calc R C15 C 0.5629(3) 0.35051(15) 0.38539(12) 0.0229(4) Uani 1 1 d . H15A H 0.438205 0.351069 0.369286 0.034 Uiso 1 1 calc GR H15B H 0.613961 0.284322 0.368901 0.034 Uiso 1 1 calc GR H15C H 0.623549 0.405009 0.352088 0.034 Uiso 1 1 calc GR C14 C 0.9927(3) 0.57637(17) 0.62513(13) 0.0246(4) Uani 1 1 d . H14A H 1.011122 0.650442 0.623182 0.037 Uiso 1 1 calc GR H14B H 1.075578 0.542778 0.583714 0.037 Uiso 1 1 calc GR H14C H 1.011521 0.551600 0.687562 0.037 Uiso 1 1 calc GR H2 H 0.921(4) 0.681(2) 0.4620(18) 0.037 Uiso 1 1 d R H1 H 0.289(4) 0.278(2) 0.9512(17) 0.037 Uiso 1 1 d 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 0.0178(7) 0.0225(7) 0.0155(6) 0.0057(5) -0.0008(5) -0.0066(5) O2 0.0162(7) 0.0147(6) 0.0190(6) -0.0002(5) 0.0069(5) -0.0013(5) C6 0.0153(9) 0.0147(8) 0.0122(7) 0.0012(6) -0.0010(7) 0.0019(7) C3 0.0149(9) 0.0156(8) 0.0120(7) -0.0002(6) -0.0024(7) 0.0003(7) C5 0.0127(9) 0.0135(8) 0.0131(7) -0.0005(6) 0.0028(6) 0.0008(6) C7 0.0100(8) 0.0153(8) 0.0127(7) -0.0002(6) -0.0011(7) 0.0002(7) C4 0.0134(9) 0.0167(8) 0.0138(7) -0.0014(6) -0.0008(7) 0.0009(7) C2 0.0125(9) 0.0115(7) 0.0127(7) -0.0001(6) -0.0004(7) 0.0016(7) C1 0.0120(8) 0.0123(8) 0.0145(8) 0.0010(6) -0.0008(7) -0.0007(7) C8 0.0145(9) 0.0146(8) 0.0149(8) -0.0029(7) -0.0010(7) 0.0007(7) C11 0.0134(9) 0.0134(8) 0.0149(8) 0.0020(6) -0.0002(7) -0.0005(7) C10 0.0230(10) 0.0121(8) 0.0188(8) 0.0036(7) 0.0038(8) 0.0027(7) C13 0.0244(10) 0.0174(9) 0.0149(8) 0.0009(7) 0.0028(7) 0.0033(8) C9 0.0216(10) 0.0128(8) 0.0212(9) -0.0040(7) 0.0027(8) 0.0000(7) C12 0.0174(9) 0.0212(9) 0.0147(8) 0.0022(7) 0.0002(7) -0.0058(8) C15 0.0288(11) 0.0224(10) 0.0174(8) -0.0052(7) -0.0006(8) 0.0037(8) C14 0.0160(10) 0.0387(11) 0.0189(8) 0.0028(8) -0.0019(8) -0.0068(9) 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' O O 0.0106 0.0060 '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' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle C12 O1 H1 109.1(17) C5 O2 H2 107.5(17) H6A C6 H6B 107.9 C5 C6 H6A 109.2 C5 C6 H6B 109.2 C5 C6 C7 111.92(14) C7 C6 H6A 109.2 C7 C6 H6B 109.2 C4 C3 H3 117.6 C4 C3 C2 124.80(15) C2 C3 H3 117.6 O2 C5 C6 107.38(14) O2 C5 H5 108.5 O2 C5 C4 110.94(14) C6 C5 H5 108.5 C4 C5 C6 112.89(14) C4 C5 H5 108.5 C6 C7 H7 108.0 C6 C7 C2 107.31(13) C6 C7 C8 113.46(14) C2 C7 H7 108.0 C8 C7 H7 108.0 C8 C7 C2 111.92(13) C3 C4 C5 121.38(16) C3 C4 C14 122.64(16) C14 C4 C5 115.94(15) C3 C2 C7 109.64(14) C3 C2 H2A 107.2 C3 C2 C1 113.49(14) C7 C2 H2A 107.2 C1 C2 C7 111.82(13) C1 C2 H2A 107.2 C2 C1 H1A 106.9 C2 C1 C11 113.81(13) C11 C1 H1A 106.9 C10 C1 C2 109.65(14) C10 C1 H1A 106.9 C10 C1 C11 112.18(14) C7 C8 H8 108.2 C9 C8 C7 109.89(14) C9 C8 H8 108.2 C9 C8 C15 110.23(15) C15 C8 C7 112.12(14) C15 C8 H8 108.2 C1 C11 H11 107.9 C13 C11 C1 113.06(14) C13 C11 H11 107.9 C12 C11 C1 110.73(14) C12 C11 H11 107.9 C12 C11 C13 109.19(15) C1 C10 H10A 109.4 C1 C10 H10B 109.4 H10A C10 H10B 108.0 C9 C10 C1 111.23(15) C9 C10 H10A 109.4 C9 C10 H10B 109.4 C11 C13 H13A 109.5 C11 C13 H13B 109.5 C11 C13 H13C 109.5 H13A C13 H13B 109.5 H13A C13 H13C 109.5 H13B C13 H13C 109.5 C8 C9 H9A 109.2 C8 C9 H9B 109.2 C10 C9 C8 112.17(14) C10 C9 H9A 109.2 C10 C9 H9B 109.2 H9A C9 H9B 107.9 O1 C12 C11 108.03(14) O1 C12 H12A 110.1 O1 C12 H12B 110.1 C11 C12 H12A 110.1 C11 C12 H12B 110.1 H12A C12 H12B 108.4 C8 C15 H15A 109.5 C8 C15 H15B 109.5 C8 C15 H15C 109.5 H15A C15 H15B 109.5 H15A C15 H15C 109.5 H15B C15 H15C 109.5 C4 C14 H14A 109.5 C4 C14 H14B 109.5 C4 C14 H14C 109.5 H14A C14 H14B 109.5 H14A C14 H14C 109.5 H14B C14 H14C 109.5 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance O1 C12 1.429(2) O1 H1 0.86(3) O2 C5 1.445(2) O2 H2 0.86(3) C6 H6A 0.9900 C6 H6B 0.9900 C6 C5 1.519(3) C6 C7 1.534(2) C3 H3 0.9500 C3 C4 1.334(3) C3 C2 1.513(3) C5 H5 1.0000 C5 C4 1.517(2) C7 H7 1.0000 C7 C2 1.547(2) C7 C8 1.543(2) C4 C14 1.507(3) C2 H2A 1.0000 C2 C1 1.546(2) C1 H1A 1.0000 C1 C11 1.547(2) C1 C10 1.536(2) C8 H8 1.0000 C8 C9 1.529(2) C8 C15 1.535(2) C11 H11 1.0000 C11 C13 1.531(2) C11 C12 1.528(2) C10 H10A 0.9900 C10 H10B 0.9900 C10 C9 1.528(2) C13 H13A 0.9800 C13 H13B 0.9800 C13 H13C 0.9800 C9 H9A 0.9900 C9 H9B 0.9900 C12 H12A 0.9900 C12 H12B 0.9900 C15 H15A 0.9800 C15 H15B 0.9800 C15 H15C 0.9800 C14 H14A 0.9800 C14 H14B 0.9800 C14 H14C 0.9800