Synthesis of [3,3-2H2]-Dihydroartemisinic Acid to Measure the Rate of Nonenzymatic Conversion of Dihydroartemisinic Acid to Artemisinin
Varela, Kaitlyn; Arman, Hadi D.; Yoshimoto, Francis K.; Journal of Natural Products  (2019) –; doi:10.1021/acs.jnatprod.9b00686

data_1556701
_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_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