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_1571949
_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         'C19 H19 Br O3'
_chemical_formula_sum            'C19 H19 Br O3'
_chemical_formula_weight         375.25
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2018-02-22
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2024-01-23 deposited with the CCDC.	2024-06-13 downloaded from the CCDC.
;
_cell_angle_alpha                90.265(4)
_cell_angle_beta                 105.787(4)
_cell_angle_gamma                106.880(4)
_cell_formula_units_Z            2
_cell_length_a                   8.0674(3)
_cell_length_b                   10.0413(5)
_cell_length_c                   11.4509(5)
_cell_measurement_reflns_used    10446
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      74.4480
_cell_measurement_theta_min      4.0290
_cell_volume                     850.63(7)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_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      N~2~
_diffrn_ambient_temperature      120(2)
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 10.3613
_diffrn_detector_type            'Agilent Diffraction Atlas detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.980
_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    -50.00  34.00   1.00    2.50    --  -38.50  38.00 -60.00   84
  2  \w   -109.00 -12.00   1.00    2.50    --  -38.50 -57.00   0.00   97
  3  \w    -65.00  32.00   1.00    2.50    --  -38.50  57.00 150.00   97
  4  \w      1.00  83.00   1.00    2.50    --   43.32 -99.00-150.00   82
  5  \w      1.00  83.00   1.00    2.50    --   43.32 -99.00-120.00   82
  6  \w     35.00  98.00   1.00   10.00    --  106.13 -45.00 -60.00   63
  7  \w     31.00  91.00   1.00   10.00    --  106.13 -30.00-120.00   60
  8  \w     32.00 138.00   1.00   10.00    --  106.13 -77.00 120.00  106
  9  \w     31.00  91.00   1.00   10.00    --  106.13 -30.00  90.00   60
 10  \w     25.00 109.00   1.00   10.00    --  106.13 -95.00  60.00   84
 11  \w     25.00 109.00   1.00   10.00    --  106.13 -95.00-120.00   84
 12  \w     35.00  98.00   1.00   10.00    --  106.13 -45.00-150.00   63
 13  \w     35.00 121.00   1.00   10.00    --  106.13-125.00 -60.00   86
 14  \w     31.00  91.00   1.00   10.00    --  106.13 -30.00 120.00   60
 15  \w     35.00  98.00   1.00   10.00    --  106.13 -45.00  30.00   63
 16  \w     31.00  91.00   1.00   10.00    --  106.13 -30.00  60.00   60
 17  \w     25.00 109.00   1.00   10.00    --  106.13 -95.00 -30.00   84
 18  \w     19.00 178.00   1.00   10.00    --  106.13   0.00 -90.00  159
 19  \w    -50.00  34.00   1.00    2.50    --  -38.50  38.00  60.00   84
 20  \w     17.00 113.00   1.00    2.50    --   43.32  57.00 -90.00   96
 21  \w     12.00 117.00   1.00    2.50    --   43.32  77.00 150.00  105
 22  \w     17.00 113.00   1.00    2.50    --   43.32  57.00  60.00   96
 23  \w     12.00 117.00   1.00    2.50    --   43.32  77.00 -60.00  105
 24  \w     82.00 178.00   1.00   10.00    --  106.13  30.00 -30.00   96
 25  \w     75.00 178.00   1.00   10.00    --  106.13  77.00 150.00  103
 26  \w     61.00 178.00   1.00   10.00    --  106.13  15.00  90.00  117
 27  \w     82.00 177.00   1.00   10.00    --  106.13  45.00 -90.00   95
 28  \w     79.00 176.00   1.00   10.00    --  106.13  61.00-150.00   97
 29  \w     79.00 176.00   1.00   10.00    --  106.13  61.00   0.00   97
 30  \w     75.00 178.00   1.00   10.00    --  106.13  77.00  60.00  103
 31  \w     79.00 176.00   1.00   10.00    --  106.13  61.00 -30.00   97
 32  \w     75.00 178.00   1.00   10.00    --  106.13  77.00-180.00  103
 33  \w     79.00 176.00   1.00   10.00    --  106.13  61.00 120.00   97
 34  \w     12.00  67.00   1.00    2.50    --   43.32  77.00  90.00   55
;
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'SuperNova, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1419749000
_diffrn_orient_matrix_UB_12      0.1015917000
_diffrn_orient_matrix_UB_13      -0.0504568000
_diffrn_orient_matrix_UB_21      0.1122728000
_diffrn_orient_matrix_UB_22      -0.1028947000
_diffrn_orient_matrix_UB_23      0.0193747000
_diffrn_orient_matrix_UB_31      -0.1029666000
_diffrn_orient_matrix_UB_32      -0.0707896000
_diffrn_orient_matrix_UB_33      -0.1295689000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0294
_diffrn_reflns_av_unetI/netI     0.0173
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            16326
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.626
_diffrn_reflns_theta_min         4.029
_diffrn_source                   'microfocus sealed tube'
_diffrn_source_type              'Agilent Diffraction microfocus tube'
_exptl_absorpt_coefficient_mu    3.393
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.455
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
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    1.465
_exptl_crystal_description       needle
_exptl_crystal_F_000             384
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: diethyl ether, petroleum ether'
_exptl_crystal_size_max          0.391
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.028
_refine_diff_density_max         0.362
_refine_diff_density_min         -0.315
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         3423
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0242
_refine_ls_R_factor_gt           0.0234
_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^)+(0.0326P)^2^+0.5214P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0612
_refine_ls_wR_factor_ref         0.0617
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3321
_reflns_number_total             3423
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc03232b2.cif
_cod_data_source_block           30
_cod_depositor_comments
'Adding full bibliography for 1571943--1571950.cif.'
_cod_database_code               1571949
_shelx_shelxl_version_number     2018/1
_chemical_oxdiff_formula         'C19 H19 Br O3'
_chemical_oxdiff_usercomment
'REARDG #17455 SN-1272 IN FOMBLIN FILM ON A MICROMOUNT FOR REA/RD'
_shelx_estimated_absorpt_t_max   0.911
_shelx_estimated_absorpt_t_min   0.350
_reflns_odcompleteness_completeness 100.00
_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
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C12(H12A,H12B), C20(H20A,H20B)
2.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C8(H8), C14(H14), C15(H15), C17(H17), C18(H18), C21(H21)
2.d X=CH2 refined with riding coordinates:
 C22(H22A,H22B)
2.e Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C)
;
_shelx_res_checksum              45887
_shelx_hkl_checksum              8778
_olex2_date_sample_data_collection 2018-02-20
_olex2_date_sample_submission    2018-01-16
_olex2_submission_original_sample_id RA-320-001
_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 1.253
_oxdiff_exptl_absorpt_empirical_full_min 0.710