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_1571950
_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         'C27 H26 O3'
_chemical_formula_sum            'C27 H26 O3'
_chemical_formula_weight         398.48
_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   mixed
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2018-09-05
_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                 102.695(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   18.6576(9)
_cell_length_b                   11.7041(5)
_cell_length_c                   10.0865(3)
_cell_measurement_reflns_used    3332
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      73.7140
_cell_measurement_theta_min      4.4780
_cell_volume                     2148.75(16)
_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 4.2207
_diffrn_detector_type            'Agilent Diffraction Titan S2 detector'
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.949
_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   -113.00 -25.00   1.00   20.00    --  -42.81 -38.00  30.00   88
  2  \w    -49.00 -22.00   1.00   20.00    --  -42.81  38.00-180.00   27
  3  \w    -92.00  -2.00   1.00   20.00    --  -42.81 125.00-180.00   90
  4  \w     94.00 170.00   1.00   80.00    --  103.32 125.00-150.00   76
  5  \w    143.00 175.00   1.00   80.00    --  103.32  77.00 -90.00   32
  6  \w     40.00 110.00   1.00   80.00    --  103.32 -94.00-150.00   70
  7  \w     88.00 117.00   1.00   80.00    --  103.32-125.00  60.00   29
  8  \w     32.00  63.00   1.00   80.00    --  103.32-125.00  60.00   31
  9  \w     43.00  87.00   1.00   80.00    --  103.32 -45.00-180.00   44
 10  \w     74.00 127.00   1.00   80.00    --  103.32  77.00 -90.00   53
 11  \w     54.00  84.00   1.00   80.00    --  103.32 -94.00 150.00   30
 12  \w     31.00  97.00   1.00   80.00    --  103.32   0.00  60.00   66
;
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'SuperNova, Titan 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      0.0074255000
_diffrn_orient_matrix_UB_12      -0.1310418000
_diffrn_orient_matrix_UB_13      -0.0019116000
_diffrn_orient_matrix_UB_21      -0.0841561000
_diffrn_orient_matrix_UB_22      -0.0111960000
_diffrn_orient_matrix_UB_23      -0.0444180000
_diffrn_orient_matrix_UB_31      0.0053994000
_diffrn_orient_matrix_UB_32      0.0050157000
_diffrn_orient_matrix_UB_33      -0.1501017000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0423
_diffrn_reflns_av_unetI/netI     0.0505
_diffrn_reflns_Laue_measured_fraction_full 0.979
_diffrn_reflns_Laue_measured_fraction_max 0.949
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            8284
_diffrn_reflns_point_group_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.949
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.821
_diffrn_reflns_theta_min         2.427
_diffrn_source                   'microfocus sealed tube'
_diffrn_source_type              'Agilent Diffraction microfocus tube'
_exptl_absorpt_coefficient_mu    0.625
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.745
_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    1.232
_exptl_crystal_description       needle
_exptl_crystal_F_000             848
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: diethyl ether, pentane'
_exptl_crystal_size_max          0.402
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.026
_refine_diff_density_max         0.400
_refine_diff_density_min         -0.351
_refine_diff_density_rms         0.065
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.133
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     331
_refine_ls_number_reflns         4132
_refine_ls_number_restraints     180
_refine_ls_restrained_S_all      1.155
_refine_ls_R_factor_all          0.0934
_refine_ls_R_factor_gt           0.0584
_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^)+(0.0828P)^2^+1.5833P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1526
_refine_ls_wR_factor_ref         0.2029
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2758
_reflns_number_total             4132
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc03232b2.cif
_cod_data_source_block           3-simonsol-F
_cod_depositor_comments
'Adding full bibliography for 1571943--1571950.cif.'
_cod_original_cell_volume        2148.74(16)
_cod_database_code               1571950
_nottingham_internal_coll_name   REARDI
_nottingham_internal_coll_number 17626
_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   10/04/2018
_nottingham_internal_coll_location NOTTS
_nottingham_internal_coll_instrument 'GVA, PL13110002'
_nottingham_internal_process_date 12/04/2018
_nottingham_internal_process_user pczwl
_nottingham_internal_solution_date 25/4/2018
_nottingham_internal_solution_user pczwl
_nottingham_internal_refinement_date 25/4/2018
_nottingham_internal_refinement_user pczwl
_nottingham_internal_validation_date 7/6/2018
_nottingham_internal_validation_user pczwl
_nottingham_internal_archive_date 7/6/2018
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C27 H26 O3'
_chemical_oxdiff_usercomment
'REARDI #17626 GVA-1420 IN FOMBLIN FILM ON A MICROMOUNT FOR REA/RD'
_shelx_estimated_absorpt_t_max   0.984
_shelx_estimated_absorpt_t_min   0.787
_reflns_odcompleteness_completeness 97.88
_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. Restrained distances
 C22-C21 \\sim C22A-C21 \\sim C26-C25 \\sim C29-C28 \\sim C28-C29A \\sim
C25-C26A
 with sigma of 0.02
 C27-C26 \\sim C30A-C29A \\sim C30-C29 \\sim C23A-C22A \\sim C23-C22 \\sim
C26A-C27A
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
C25 \\sim C26 \\sim C26A \\sim C27 \\sim C27A \\sim C28 \\sim C29 \\sim C29A
\\sim C30 \\sim C30A: within 2A with sigma of 0.01 and sigma for terminal atoms
of 0.02
4. Rigid body (RIGU) restrains
 C21, C22, C22A, C23, C23A, C25, C26, C26A, C27, C27A, C28, C29, C29A, C30, C30A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Sof(H28D)=Sof(H28C)=Sof(C29A)=Sof(H29A)=Sof(C30A)=Sof(H30C)=Sof(H30D)=1-FVAR(1)
 Sof(H28a)=Sof(H28b)=Sof(C29)=Sof(H29)=Sof(C30)=Sof(H30a)=Sof(H30b)=FVAR(1)
 Sof(H21C)=Sof(H21D)=Sof(C22A)=Sof(H22A)=Sof(C23A)=Sof(H23C)=Sof(H23D)=1-FVAR(2)
 Sof(H21a)=Sof(H21b)=Sof(C22)=Sof(H22)=Sof(C23)=Sof(H23a)=Sof(H23b)=FVAR(2)
 Sof(H25C)=Sof(H25D)=Sof(C26A)=Sof(H26A)=Sof(C27A)=Sof(H27C)=Sof(H27D)=1-FVAR(3)
 Sof(H25a)=Sof(H25b)=Sof(C26)=Sof(H26)=Sof(C27)=Sof(H27a)=Sof(H27b)=FVAR(3)
6.a Ternary CH refined with riding coordinates:
 C13(H13)
6.b Secondary CH2 refined with riding coordinates:
 C1(H1a,H1b), C21(H21a,H21b), C21(H21C,H21D), C25(H25a,H25b), C25(H25C,H25D),
 C28(H28a,H28b), C28(H28D,H28C)
6.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C7(H7), C9(H9), C10(H10), C16(H16), C18(H18), C19(H19), C22(H22),
 C22A(H22A), C26(H26), C26A(H26A), C29(H29), C29A(H29A)
6.d X=CH2 refined with riding coordinates:
 C23(H23a,H23b), C23A(H23C,H23D), C27(H27a,H27b), C27A(H27C,H27D), C30(H30a,
 H30b), C30A(H30C,H30D)
;
_shelx_res_checksum              83570
_shelx_hkl_checksum              12038
_olex2_date_sample_data_collection 2018-04-12
_olex2_date_sample_submission    2018-04-09
_olex2_exptl_crystal_mounting_method 'in fomblin film on a micromount'
_olex2_submission_original_sample_id RA-308-004
_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 1.355
_oxdiff_exptl_absorpt_empirical_full_min 0.703