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_1571947
_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 H18 B2 O4'
_chemical_formula_sum            'C18 H18 B2 O4'
_chemical_formula_weight         319.94
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2018-02-13
_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
_cell_angle_beta                 101.804(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   31.4184(9)
_cell_length_b                   4.96092(16)
_cell_length_c                   21.7474(7)
_cell_measurement_reflns_used    8544
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      73.1530
_cell_measurement_theta_min      4.5360
_cell_volume                     3317.96(18)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (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      '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 5.2349
_diffrn_detector_type            'Agilent Diffraction Atlas S2 detector'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.984
_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   20.00    --  -38.50  38.00 120.00   84
  2  \w    -90.00   2.00   1.00   20.00    --  -38.50 120.00 -54.00   92
  3  \w    -36.00  80.00   1.00   20.00    --   42.83 -19.00 -90.00  116
  4  \w     33.00 122.00   1.00   80.00    --  104.50-125.00 -90.00   89
  5  \w     33.00  98.00   1.00   80.00    --  104.50 -45.00  90.00   65
  6  \w     31.00 136.00   1.00   80.00    --  104.50 -77.00 -60.00  105
  7  \w     30.00  91.00   1.00   80.00    --  104.50 -30.00 -60.00   61
  8  \w     30.00  91.00   1.00   80.00    --  104.50 -30.00  30.00   61
  9  \w     30.00  91.00   1.00   80.00    --  104.50 -30.00-180.00   61
 10  \w     73.00 178.00   1.00   80.00    --  104.50  77.00  60.00  105
 11  \w     30.00  91.00   1.00   80.00    --  104.50 -30.00 -30.00   61
 12  \w     16.00 113.00   1.00   20.00    --   42.83  57.00 120.00   97
 13  \w     16.00 113.00   1.00   20.00    --   42.83  57.00-120.00   97
 14  \w     11.00 117.00   1.00   20.00    --   42.83  77.00   0.00  106
 15  \w     81.00 178.00   1.00   80.00    --  104.50  30.00-120.00   97
 16  \w     81.00 178.00   1.00   80.00    --  104.50  30.00 150.00   97
 17  \w     77.00 175.00   1.00   80.00    --  104.50  61.00  30.00   98
 18  \w     80.00 176.00   1.00   80.00    --  104.50  45.00 -90.00   96
 19  \w     23.00 109.00   1.00   80.00    --  104.50 -94.00  90.00   86
 20  \w     59.00 178.00   1.00   80.00    --  104.50  15.00   0.00  119
 21  \w   -110.00 -55.00   1.00   20.00    --  -38.50-154.00  64.00   55
 22  \w    -94.00  -2.00   1.00   20.00    --  -38.50 125.00-180.00   92
 23  \w     11.00 117.00   1.00   20.00    --   42.83  77.00 -90.00  106
 24  \w     80.00 105.00   1.00   80.00    --  104.50  45.00-180.00   25
;
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'SuperNova, Atlas S2'
_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      -0.0054633000
_diffrn_orient_matrix_UB_12      0.2908389000
_diffrn_orient_matrix_UB_13      0.0219773000
_diffrn_orient_matrix_UB_21      -0.0494110000
_diffrn_orient_matrix_UB_22      -0.0190106000
_diffrn_orient_matrix_UB_23      -0.0254186000
_diffrn_orient_matrix_UB_31      -0.0061681000
_diffrn_orient_matrix_UB_32      -0.1068536000
_diffrn_orient_matrix_UB_33      0.0641253000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0353
_diffrn_reflns_av_unetI/netI     0.0179
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       38
_diffrn_reflns_limit_h_min       -38
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            19859
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.746
_diffrn_reflns_theta_min         4.154
_diffrn_source                   'microfocus sealed tube'
_diffrn_source_type              'Agilent Diffraction microfocus tube'
_exptl_absorpt_coefficient_mu    0.706
_exptl_absorpt_correction_T_max  0.987
_exptl_absorpt_correction_T_min  0.834
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43 (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    1.281
_exptl_crystal_description       needle
_exptl_crystal_F_000             1344
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: diethyl ether, pentane'
_exptl_crystal_size_max          0.347
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.019
_refine_diff_density_max         0.351
_refine_diff_density_min         -0.380
_refine_diff_density_rms         0.085
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.151
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     233
_refine_ls_number_reflns         3296
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.151
_refine_ls_R_factor_all          0.0875
_refine_ls_R_factor_gt           0.0835
_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^)+(0.0859P)^2^+24.1703P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2607
_refine_ls_wR_factor_ref         0.2630
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3014
_reflns_number_total             3296
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc03232b2.cif
_cod_data_source_block           25
_cod_depositor_comments
'Adding full bibliography for 1571943--1571950.cif.'
_cod_original_cell_volume        3317.97(19)
_cod_database_code               1571947
_nottingham_internal_coll_name   REARDH
_nottingham_internal_coll_number 17457
_nottingham_internal_coll_client REA/RD
_nottingham_internal_coll_type   custom
_nottingham_internal_coll_frame_method '\w scans'
_nottingham_internal_coll_frame_time '20.00, 80.00'
_nottingham_internal_coll_frame_width 1.00
_nottingham_internal_coll_user   pczwl
_nottingham_internal_coll_date   19/01/2018
_nottingham_internal_coll_location NOTTS
_nottingham_internal_coll_instrument 'GVB, PL13110001'
_nottingham_internal_process_date 23/01/2018
_nottingham_internal_process_user pczwl
_nottingham_internal_solution_date 23/1/2018
_nottingham_internal_solution_user pczwl
_nottingham_internal_refinement_date 23/1/2018
_nottingham_internal_refinement_user pczwl
_nottingham_internal_validation_date 13/2/2018
_nottingham_internal_validation_user pczwl
_nottingham_internal_archive_date 13/2/2018
_shelx_shelxl_version_number     2018/1
_chemical_oxdiff_formula         'C18 H18 B2 O4'
_chemical_oxdiff_usercomment
'REARDH #17457 GVB-1442 IN FOMBLIN FILM ON MICROMOUNT FOR REA/RD'
_shelx_estimated_absorpt_t_max   0.987
_shelx_estimated_absorpt_t_min   0.792
_reflns_odcompleteness_completeness 99.91
_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, All C(H,H,H,H) groups
 At 1.5 times of:
  All O(H) groups
2. Others
 Sof(H14C)=Sof(H14D)=Sof(H16C)=Sof(H16D)=Sof(C15A)=Sof(H15A)=1-FVAR(1)
 Sof(H14A)=Sof(H14B)=Sof(C15)=Sof(H15)=Sof(H16A)=Sof(H16B)=FVAR(1)
3.a Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C14(H14C,H14D), C22(H22A,H22B)
3.b Aromatic/amide H refined with riding coordinates:
 C9(H9), C10(H10), C12(H12), C15(H15), C18(H18), C20(H20), C21(H21), C23(H23),
 C15A(H15A)
3.c X=CH2 refined with riding coordinates:
 C16(H16A,H16B), C16(H16C,H16D), C24(H24A,H24B)
;
_shelx_res_checksum              1395
_shelx_hkl_checksum              66200
_olex2_date_sample_data_collection 2018-01-19
_olex2_date_sample_submission    2018-01-18
_olex2_exptl_crystal_mounting_method "'in fomblin film on a micromount"
_olex2_submission_original_sample_id RA-195-001
_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 1.419
_oxdiff_exptl_absorpt_empirical_full_min 0.523