#------------------------------------------------------------------------------ #$Date: 2019-12-21 02:10:49 +0200 (Sat, 21 Dec 2019) $ #$Revision: 245459 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/55/67/1556701.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_1556701 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 H24 O' _chemical_formula_sum 'C15 H24 O' _chemical_formula_weight 220.34 _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 2019-07-18 _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 5.15450(10) _cell_length_b 14.0173(4) _cell_length_c 18.2753(4) _cell_measurement_reflns_used 8525 _cell_measurement_temperature 100(2) _cell_measurement_theta_max 29.2160 _cell_measurement_theta_min 3.6160 _cell_volume 1320.43(5) _computing_cell_refinement 'CrysAlisPro 1.171.40.54a (Rigaku OD, 2019)' _computing_data_collection 'CrysAlisPro 1.171.40.54a (Rigaku OD, 2019)' _computing_data_reduction 'CrysAlisPro 1.171.40.54a (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 100(2) _diffrn_detector 'CCD plate' _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _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 -97.00 22.00 1.00 15.00 -- -7.70 -53.00-103.00 119 2 \w -21.00 94.00 1.00 15.00 -- 4.20 38.00-120.00 115 3 \w -33.00 82.00 1.00 15.00 -- -7.70 38.00-150.00 115 4 \w -38.00 31.00 1.00 15.00 -- -7.70 57.00 0.00 69 ; _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 -0.0754115000 _diffrn_orient_matrix_UB_12 0.0271033000 _diffrn_orient_matrix_UB_13 0.0249339000 _diffrn_orient_matrix_UB_21 0.0457084000 _diffrn_orient_matrix_UB_22 -0.0286584000 _diffrn_orient_matrix_UB_23 0.0292775000 _diffrn_orient_matrix_UB_31 0.1056798000 _diffrn_orient_matrix_UB_32 0.0317225000 _diffrn_orient_matrix_UB_33 0.0050839000 _diffrn_radiation_monochromator mirror _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0330 _diffrn_reflns_av_unetI/netI 0.0184 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.999 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_number 16134 _diffrn_reflns_point_group_measured_fraction_full 1.000 _diffrn_reflns_point_group_measured_fraction_max 1.000 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 25.997 _diffrn_reflns_theta_min 2.229 _diffrn_source 'Rotating-anode X-ray tube' _diffrn_source_type 'Rigaku (Mo) X-ray Source' _exptl_absorpt_coefficient_mu 0.067 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.97332 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.40.54a (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 1.108 _exptl_crystal_description plate _exptl_crystal_F_000 488 _exptl_crystal_size_max 0.33 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.13 _refine_diff_density_max 0.189 _refine_diff_density_min -0.146 _refine_diff_density_rms 0.032 _refine_ls_abs_structure_details ; Flack x determined using 1002 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack 0.2(4) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.058 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 154 _refine_ls_number_reflns 2602 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.058 _refine_ls_R_factor_all 0.0341 _refine_ls_R_factor_gt 0.0333 _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^)+(0.0448P)^2^+0.2687P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0838 _refine_ls_wR_factor_ref 0.0848 _reflns_Friedel_coverage 0.686 _reflns_Friedel_fraction_full 1.000 _reflns_Friedel_fraction_max 1.000 _reflns_number_gt 2559 _reflns_number_total 2602 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file np9b00686_si_003.cif _cod_data_source_block cd1993a _cod_database_code 1556701 _shelx_shelxl_version_number 2016/6 _chemical_oxdiff_formula C20H20O4N2 _chemical_oxdiff_usercomment KV1-054 _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 0.991 _shelx_estimated_absorpt_t_min 0.978 _reflns_odcompleteness_completeness 99.82 _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) groups 2.a Ternary CH refined with riding coordinates: C11(H11), C5(H5), C10(H10), C1(H1A), C4(H4) 2.b Secondary CH2 refined with riding coordinates: C2(H2A,H2B), C3(H3A,H3B), C12(H12A,H12B) 2.c Aromatic/amide H refined with riding coordinates: C9(H9), C6(H6) 2.d Idealised Me refined as rotating group: C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C15(H15A,H15B,H15C) ; _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 1.054 _oxdiff_exptl_absorpt_empirical_full_min 0.938 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 0.2531(2) 0.28399(8) 0.50153(7) 0.0254(3) Uani 1 1 d . C2 C 0.6136(3) 0.55558(10) 0.56197(8) 0.0167(3) Uani 1 1 d . H2A H 0.759249 0.530572 0.591605 0.020 Uiso 1 1 calc R H2B H 0.629870 0.529058 0.511975 0.020 Uiso 1 1 calc R C11 C 0.3289(3) 0.41238(10) 0.59216(8) 0.0158(3) Uani 1 1 d . H11 H 0.502905 0.383852 0.602512 0.019 Uiso 1 1 calc R C5 C 0.3441(3) 0.67608(11) 0.66913(9) 0.0177(3) Uani 1 1 d . H5 H 0.194754 0.700305 0.639557 0.021 Uiso 1 1 calc R C10 C 0.3274(3) 0.56627(10) 0.67234(8) 0.0159(3) Uani 1 1 d . H10 H 0.150347 0.549396 0.690590 0.019 Uiso 1 1 calc R C1 C 0.3569(3) 0.52243(10) 0.59552(8) 0.0143(3) Uani 1 1 d . H1A H 0.214997 0.549707 0.564618 0.017 Uiso 1 1 calc R C9 C 0.5211(3) 0.52911(12) 0.72738(9) 0.0193(4) Uani 1 1 d . H9 H 0.608574 0.470681 0.718198 0.023 Uiso 1 1 calc R C4 C 0.5979(3) 0.71067(11) 0.63322(8) 0.0173(3) Uani 1 1 d . H4 H 0.745640 0.690070 0.664975 0.021 Uiso 1 1 calc R C3 C 0.6321(3) 0.66392(11) 0.55836(8) 0.0186(3) Uani 1 1 d . H3A H 0.497065 0.688326 0.524694 0.022 Uiso 1 1 calc R H3B H 0.803365 0.682000 0.538144 0.022 Uiso 1 1 calc R C13 C 0.1351(4) 0.36955(11) 0.64619(9) 0.0204(4) Uani 1 1 d . H13A H 0.194902 0.381150 0.696313 0.031 Uiso 1 1 calc GR H13B H 0.121197 0.300698 0.637761 0.031 Uiso 1 1 calc GR H13C H -0.035089 0.399330 0.639165 0.031 Uiso 1 1 calc GR C12 C 0.2514(3) 0.38428(11) 0.51413(9) 0.0204(4) Uani 1 1 d . H12A H 0.075228 0.409119 0.504010 0.024 Uiso 1 1 calc R H12B H 0.372273 0.415083 0.479277 0.024 Uiso 1 1 calc R C8 C 0.5713(4) 0.57770(13) 0.78927(9) 0.0265(4) Uani 1 1 d . C14 C 0.6087(4) 0.81943(11) 0.62623(10) 0.0275(4) Uani 1 1 d . H14A H 0.465276 0.841395 0.595341 0.041 Uiso 1 1 calc GR H14B H 0.774098 0.838186 0.604015 0.041 Uiso 1 1 calc GR H14C H 0.593793 0.848344 0.674876 0.041 Uiso 1 1 calc GR C6 C 0.3188(4) 0.71439(12) 0.74626(10) 0.0266(4) Uani 1 1 d . H6 H 0.220779 0.770526 0.755413 0.032 Uiso 1 1 calc R C7 C 0.4353(4) 0.66865(14) 0.80138(10) 0.0310(4) Uani 1 1 d . C15 C 0.7593(5) 0.54442(15) 0.84602(11) 0.0397(5) Uani 1 1 d . H15A H 0.667337 0.533243 0.892158 0.060 Uiso 1 1 calc GR H15B H 0.892942 0.593220 0.853390 0.060 Uiso 1 1 calc GR H15C H 0.841022 0.484969 0.829729 0.060 Uiso 1 1 calc GR H7 H 0.423(5) 0.6923(17) 0.8500(14) 0.048 Uiso 1 1 d R H1 H 0.413(6) 0.2640(19) 0.5018(17) 0.060 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 0.0179(5) 0.0188(6) 0.0395(7) -0.0113(5) 0.0008(6) -0.0006(5) C2 0.0181(8) 0.0168(7) 0.0152(7) -0.0012(6) 0.0029(7) 0.0003(6) C11 0.0130(7) 0.0151(7) 0.0192(8) 0.0001(6) -0.0001(6) 0.0008(6) C5 0.0150(7) 0.0178(7) 0.0204(8) -0.0030(6) 0.0002(7) 0.0018(6) C10 0.0138(7) 0.0182(7) 0.0158(7) -0.0019(6) 0.0038(6) -0.0010(6) C1 0.0127(7) 0.0149(7) 0.0153(7) -0.0001(6) -0.0009(6) 0.0022(6) C9 0.0189(8) 0.0223(8) 0.0166(8) 0.0035(6) 0.0029(7) -0.0022(7) C4 0.0173(8) 0.0173(8) 0.0171(8) -0.0006(6) 0.0001(6) -0.0005(6) C3 0.0210(8) 0.0181(8) 0.0167(8) 0.0024(6) 0.0027(7) -0.0007(6) C13 0.0188(8) 0.0177(7) 0.0247(8) 0.0013(6) 0.0013(7) -0.0012(6) C12 0.0215(8) 0.0173(8) 0.0223(9) -0.0045(6) 0.0008(7) -0.0010(6) C8 0.0256(9) 0.0354(9) 0.0184(8) 0.0061(7) 0.0002(7) -0.0132(8) C14 0.0386(11) 0.0186(8) 0.0253(9) -0.0032(7) 0.0010(8) -0.0040(8) C6 0.0293(10) 0.0231(8) 0.0273(9) -0.0104(7) 0.0101(8) -0.0049(7) C7 0.0411(11) 0.0341(10) 0.0176(8) -0.0083(7) 0.0057(8) -0.0135(9) C15 0.0426(12) 0.0508(12) 0.0257(10) 0.0124(9) -0.0128(9) -0.0208(11) 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' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle C12 O1 H1 108.9(18) H2A C2 H2B 107.9 C1 C2 H2A 109.2 C1 C2 H2B 109.2 C3 C2 H2A 109.2 C3 C2 H2B 109.2 C3 C2 C1 111.98(12) C1 C11 H11 107.9 C13 C11 H11 107.9 C13 C11 C1 115.23(13) C13 C11 C12 109.27(13) C12 C11 H11 107.9 C12 C11 C1 108.47(12) C10 C5 H5 108.4 C4 C5 H5 108.4 C4 C5 C10 112.17(12) C6 C5 H5 108.4 C6 C5 C10 108.27(13) C6 C5 C4 110.97(13) C5 C10 H10 107.4 C1 C10 C5 110.97(12) C1 C10 H10 107.4 C9 C10 C5 109.43(13) C9 C10 H10 107.4 C9 C10 C1 113.85(13) C2 C1 C11 111.51(12) C2 C1 C10 109.23(12) C2 C1 H1A 106.9 C11 C1 H1A 106.9 C10 C1 C11 115.08(12) C10 C1 H1A 106.9 C10 C9 H9 119.6 C8 C9 C10 120.85(15) C8 C9 H9 119.6 C5 C4 H4 108.0 C3 C4 C5 110.14(13) C3 C4 H4 108.0 C3 C4 C14 110.40(13) C14 C4 C5 112.30(14) C14 C4 H4 108.0 C2 C3 C4 112.45(12) C2 C3 H3A 109.1 C2 C3 H3B 109.1 C4 C3 H3A 109.1 C4 C3 H3B 109.1 H3A C3 H3B 107.8 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 O1 C12 C11 113.73(13) O1 C12 H12A 108.8 O1 C12 H12B 108.8 C11 C12 H12A 108.8 C11 C12 H12B 108.8 H12A C12 H12B 107.7 C9 C8 C7 118.24(17) C9 C8 C15 123.39(18) C7 C8 C15 118.36(17) 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 C5 C6 H6 120.2 C7 C6 C5 119.53(16) C7 C6 H6 120.2 C8 C7 H7 118.3(15) C6 C7 C8 121.08(16) C6 C7 H7 120.5(15) 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 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance O1 C12 1.4246(18) O1 H1 0.87(3) C2 H2A 0.9900 C2 H2B 0.9900 C2 C1 1.530(2) C2 C3 1.523(2) C11 H11 1.0000 C11 C1 1.5505(19) C11 C13 1.528(2) C11 C12 1.532(2) C5 H5 1.0000 C5 C10 1.543(2) C5 C4 1.542(2) C5 C6 1.514(2) C10 H10 1.0000 C10 C1 1.540(2) C10 C9 1.510(2) C1 H1A 1.0000 C9 H9 0.9500 C9 C8 1.345(2) C4 H4 1.0000 C4 C3 1.527(2) C4 C14 1.531(2) C3 H3A 0.9900 C3 H3B 0.9900 C13 H13A 0.9800 C13 H13B 0.9800 C13 H13C 0.9800 C12 H12A 0.9900 C12 H12B 0.9900 C8 C7 1.472(3) C8 C15 1.494(3) C14 H14A 0.9800 C14 H14B 0.9800 C14 H14C 0.9800 C6 H6 0.9500 C6 C7 1.337(3) C7 H7 0.95(2) C15 H15A 0.9800 C15 H15B 0.9800 C15 H15C 0.9800