Total synthesis, biological evaluation and biosynthetic re-evaluation of <i>Illicium</i>-derived neolignans.
Arnold, Robert E.; Saska, Jan; Mesquita-Ribeiro, Raquel; Dajas-Bailador, Federico; Taylor, Laurence; Lewis, William; Argent, Stephen; Shao, Huiling; Houk, Kendall N.; Denton, Ross M.; Chemical science 15 (2024) 11783–11793; doi:10.1039/d4sc03232b

data_1571946
_publ_section_title
;
 Total synthesis, biological evaluation and biosynthetic re-evaluation of
 <i>Illicium</i>-derived neolignans.
;
_journal_issue                   30
_journal_name_full               'Chemical science'
_journal_page_first              11783
_journal_page_last               11793
_journal_paper_doi               10.1039/d4sc03232b
_journal_volume                  15
_journal_year                    2024
_chemical_formula_moiety         'C18 H17 Br O2'
_chemical_formula_sum            'C18 H17 Br O2'
_chemical_formula_weight         345.23
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2018-07-09
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2024-01-23 deposited with the CCDC.	2024-06-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 108.692(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   17.6068(5)
_cell_length_b                   7.4294(2)
_cell_length_c                   12.3043(4)
_cell_measurement_reflns_used    17249
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      74.3420
_cell_measurement_theta_min      3.8030
_cell_volume                     1524.61(8)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_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    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_environment      'N2 gas'
_diffrn_ambient_temperature      120(2)
_diffrn_crystal_treatment        'flash frozen in gaseous N2'
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 10.3613
_diffrn_detector_type            'Agilent Diffraction Atlas detector'
_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   -107.00 -20.00   1.00    1.00    --  -38.50 -38.00-180.00   87
  2  \w    -48.00  28.00   1.00    1.00    --  -38.50  38.00   0.00   76
  3  \w     21.00  54.00   1.00    1.00    --   43.13  57.00-180.00   33
  4  \w     22.00 100.00   1.00    1.00    --   43.13  57.00  30.00   78
  5  \w     26.00 112.00   1.00    1.00    --   43.13  57.00  90.00   86
  6  \w     43.00  96.00   1.00    1.00    --   43.13-125.00 -30.00   53
  7  \w     76.00 102.00   1.00    1.00    --  106.13  77.00 -30.00   26
  8  \w     36.00  63.00   1.00    1.00    --  106.13 -30.00 -60.00   27
  9  \w     49.00  91.00   1.00    1.00    --  106.13 -30.00-120.00   42
 10  \w     75.00 100.00   1.00    1.00    --  106.13  77.00   0.00   25
 11  \w     36.00  92.00   1.00    1.00    --  106.13 -45.00-180.00   56
 12  \w     75.00 101.00   1.00    1.00    --  106.13  77.00  60.00   26
 13  \w    116.00 172.00   1.00    1.00    --  106.13  77.00  60.00   56
 14  \w     66.00 117.00   1.00    1.00    --  106.13-125.00   0.00   51
 15  \w     79.00 105.00   1.00    1.00    --  106.13  61.00   0.00   26
 16  \w     80.00 111.00   1.00    1.00    --  106.13  61.00  90.00   31
 17  \w     79.00 119.00   1.00    1.00    --  106.13  61.00  60.00   40
 18  \w     80.00 106.00   1.00    1.00    --  106.13  61.00  30.00   26
 19  \w     41.00  85.00   1.00    1.00    --  106.13 -30.00 -30.00   44
 20  \w     79.00 105.00   1.00    1.00    --  106.13  61.00 -30.00   26
 21  \w     75.00 120.00   1.00    1.00    --  106.13  77.00  90.00   45
 22  \w    108.00 177.00   1.00    1.00    --  106.13 107.00 135.00   69
 23  \w    114.00 177.00   1.00    1.00    --  106.13  77.00 -30.00   63
 24  \w     83.00 116.00   1.00    1.00    --  106.13  45.00  60.00   33
 25  \w     89.00 121.00   1.00    1.00    --  106.13  45.00 -30.00   32
 26  \w     82.00 112.00   1.00    1.00    --  106.13  45.00  90.00   30
 27  \w     75.00 100.00   1.00    1.00    --  106.13  77.00  30.00   25
 28  \w     83.00 108.00   1.00    1.00    --  106.13  45.00   0.00   25
 29  \w     83.00 109.00   1.00    1.00    --  106.13  45.00  30.00   26
 30  \w    116.00 175.00   1.00    1.00    --  106.13  45.00  30.00   59
 31  \w     27.00  82.00   1.00    1.00    --  106.13 -95.00  90.00   55
 32  \w    128.00 177.00   1.00    1.00    --  106.13  45.00 -60.00   49
 33  \w    -29.00  19.00   1.00    1.00    --  -38.50  38.00 -90.00   48
 34  \w    -61.00  28.00   1.00    1.00    --  -38.50  57.00-180.00   89
 35  \w     13.00  84.00   1.00    1.00    --   43.13  77.00 -60.00   71
 36  \w     12.00  67.00   1.00    1.00    --   43.13  77.00  90.00   55
 37  \w     14.00  40.00   1.00    1.00    --   43.13  77.00  30.00   26
 38  \w     20.00  47.00   1.00    1.00    --   43.13  77.00-120.00   27
 39  \w     57.00 110.00   1.00    1.00    --   43.13  77.00-120.00   53
 40  \w      9.00  55.00   1.00    1.00    --   43.13 -99.00  60.00   46
 41  \w     68.00 102.00   1.00    1.00    --   43.13  77.00-180.00   34
 42  \w     13.00  54.00   1.00    1.00    --   43.13  77.00-180.00   41
 43  \w     79.00 105.00   1.00    1.00    --  106.13  61.00 120.00   26
 44  \w     79.00 111.00   1.00    1.00    --  106.13  61.00 -90.00   32
 45  \w     75.00 178.00   1.00    1.00    --  106.13  77.00-120.00  103
 46  \w     55.00  81.00   1.00    1.00    --  106.13 -95.00  60.00   26
 47  \w     75.00 101.00   1.00    1.00    --  106.13  77.00-180.00   26
 48  \w     66.00 136.00   1.00    1.00    --  106.13 -77.00-180.00   70
 49  \w     79.00 147.00   1.00    1.00    --  106.13  61.00-150.00   68
 50  \w     34.00  62.00   1.00    1.00    --  106.13 -77.00-180.00   28
 51  \w     79.00 133.00   1.00    1.00    --  106.13  61.00 150.00   54
 52  \w     82.00 127.00   1.00    1.00    --  106.13  61.00-180.00   45
 53  \w     81.00 124.00   1.00    1.00    --  106.13  61.00-120.00   43
 54  \w     75.00 101.00   1.00    1.00    --  106.13  77.00 150.00   26
 55  \w    148.00 174.00   1.00    1.00    --  106.13  61.00 -60.00   26
 56  \w     80.00 106.00   1.00    1.00    --  106.13  61.00 -60.00   26
 57  \w     82.00 108.00   1.00    1.00    --  106.13 -95.00  60.00   26
 58  \w     75.00 101.00   1.00    1.00    --  106.13  77.00-150.00   26
 59  \w     76.00 102.00   1.00    1.00    --  106.13  77.00 120.00   26
 60  \w    150.00 176.00   1.00    1.00    --  106.13  77.00 120.00   26
 61  \w    111.00 137.00   1.00    1.00    --  106.13  61.00 120.00   26
 62  \w     75.00 130.00   1.00    1.00    --  106.13  77.00 -90.00   55
 63  \w     36.00 106.00   1.00    1.00    --  106.13 -95.00 150.00   70
;
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'SuperNova, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_measurement_specimen_support 'MiTeGen micromount'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0044965000
_diffrn_orient_matrix_UB_12      0.0629202000
_diffrn_orient_matrix_UB_13      0.1212106000
_diffrn_orient_matrix_UB_21      0.0895497000
_diffrn_orient_matrix_UB_22      0.0443941000
_diffrn_orient_matrix_UB_23      0.0262782000
_diffrn_orient_matrix_UB_31      -0.0221851000
_diffrn_orient_matrix_UB_32      0.1925200000
_diffrn_orient_matrix_UB_33      -0.0457253000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0310
_diffrn_reflns_av_unetI/netI     0.0122
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            25893
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.554
_diffrn_reflns_theta_min         5.304
_diffrn_source                   'microfocus sealed tube'
_diffrn_source_type              'Agilent Diffraction microfocus tube'
_exptl_absorpt_coefficient_mu    3.683
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.144
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
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    1.504
_exptl_crystal_description       block
_exptl_crystal_F_000             704
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: diethyl ether, pentane'
_exptl_crystal_size_max          0.601
_exptl_crystal_size_mid          0.543
_exptl_crystal_size_min          0.233
_refine_diff_density_max         0.401
_refine_diff_density_min         -0.705
_refine_diff_density_rms         0.080
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.188
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         3083
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.188
_refine_ls_R_factor_all          0.0292
_refine_ls_R_factor_gt           0.0291
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0343P)^2^+1.4451P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0750
_refine_ls_wR_factor_ref         0.0751
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3072
_reflns_number_total             3083
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc03232b2.cif
_cod_data_source_block           34
_cod_depositor_comments
'Adding full bibliography for 1571943--1571950.cif.'
_cod_original_cell_volume        1524.62(8)
_cod_database_code               1571946
_nottingham_internal_coll_name   REARDJ
_nottingham_internal_coll_number 17781
_nottingham_internal_coll_client REA/RD
_nottingham_internal_coll_type   custom
_nottingham_internal_coll_frame_method '\w scans'
_nottingham_internal_coll_frame_time 1.00
_nottingham_internal_coll_frame_width 1.00
_nottingham_internal_coll_user   pczwl
_nottingham_internal_coll_date   09/07/2018
_nottingham_internal_coll_location NOTTS
_nottingham_internal_coll_instrument 'SN, XDA 017-09'
_nottingham_internal_process_date 09/07/2018
_nottingham_internal_process_user pczwl
_nottingham_internal_solution_date 9/7/2018
_nottingham_internal_solution_user pczwl
_nottingham_internal_refinement_date 9/7/2018
_nottingham_internal_refinement_user pczwl
_nottingham_internal_validation_date 9/7/2018
_nottingham_internal_validation_user pczwl
_nottingham_internal_archive_date 9/7/2018
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C18 H17 Br O2'
_chemical_oxdiff_usercomment
'REARDJ #17781 SN-1362 IN FOMBLIN FILM ON MICROOUNT FOR REA/RD'
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     67.13
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C5(H5)
2.b Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C15(H15A,H15B), C18(H18A,H18B)
2.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C9(H9), C10(H10), C11(H11), C16(H16), C19(H19)
2.d X=CH2 refined with riding coordinates:
 C17(H17A,H17B), C20(H20A,H20B)
;
_shelx_res_checksum              25717
_shelx_hkl_checksum              90556
_olex2_exptl_crystal_mounting_method 'in fomblin film on a Mitegen micromount'
_olex2_submission_original_sample_id RA-425-001
_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 4.380
_oxdiff_exptl_absorpt_empirical_full_min 0.754