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_1571945
_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      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2018-02-10
_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                 100.156(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.0694(3)
_cell_length_b                   10.5320(3)
_cell_length_c                   17.2799(6)
_cell_measurement_reflns_used    4257
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      74.2860
_cell_measurement_theta_min      4.1770
_cell_volume                     1624.70(9)
_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_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 0.998
_diffrn_measured_fraction_theta_max 0.961
_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     51.00  86.00   1.00    1.00    --  106.13 -30.00   0.00   35
  2  \w     54.00  89.00   1.00    1.00    --  106.13 -45.00  90.00   35
  3  \w     38.00 109.00   1.00    1.00    --  106.13 -95.00 120.00   71
  4  \w     50.00  83.00   1.00    1.00    --   43.32 -99.00  30.00   33
  5  \w     55.00  91.00   1.00    1.00    --  106.13 -30.00 -90.00   36
  6  \w     65.00  90.00   1.00    1.00    --  106.13 -30.00-180.00   25
  7  \w     50.00  89.00   1.00    1.00    --  106.13 -45.00-180.00   39
  8  \w     39.00 104.00   1.00    1.00    --  106.13 -95.00-150.00   65
  9  \w     31.00  85.00   1.00    1.00    --  106.13 -30.00-120.00   54
 10  \w     32.00  82.00   1.00    1.00    --  106.13 -30.00 -30.00   50
 11  \w    -49.00  31.00   1.00    1.00    --  -38.50  38.00-150.00   80
 12  \w    -61.00 -12.00   1.00    1.00    --  -38.50 -57.00  30.00   49
 13  \w    -37.00  33.00   1.00    1.00    --  -38.50  38.00 -90.00   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      -0.0021901000
_diffrn_orient_matrix_UB_12      -0.1456334000
_diffrn_orient_matrix_UB_13      0.0079238000
_diffrn_orient_matrix_UB_21      -0.1697838000
_diffrn_orient_matrix_UB_22      0.0041016000
_diffrn_orient_matrix_UB_23      0.0002696000
_diffrn_orient_matrix_UB_31      -0.0313630000
_diffrn_orient_matrix_UB_32      -0.0127608000
_diffrn_orient_matrix_UB_33      -0.0901961000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0244
_diffrn_reflns_av_unetI/netI     0.0245
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.961
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            6146
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.961
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.449
_diffrn_reflns_theta_min         4.939
_diffrn_source                   'microfocus sealed tube'
_diffrn_source_type              'Agilent Diffraction microfocus tube'
_exptl_absorpt_coefficient_mu    3.553
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.215
_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    1.534
_exptl_crystal_description       block
_exptl_crystal_F_000             768
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: diethyl ether, petroleum ether'
_exptl_crystal_size_max          0.719
_exptl_crystal_size_mid          0.486
_exptl_crystal_size_min          0.412
_refine_diff_density_max         0.423
_refine_diff_density_min         -0.369
_refine_diff_density_rms         0.073
_refine_ls_extinction_coef       0.0046(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/1 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.104
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         3197
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.104
_refine_ls_R_factor_all          0.0307
_refine_ls_R_factor_gt           0.0294
_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^)+(0.0465P)^2^+0.7565P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0777
_refine_ls_wR_factor_ref         0.0785
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3110
_reflns_number_total             3197
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc03232b2.cif
_cod_data_source_block           42a
_cod_depositor_comments
'Adding full bibliography for 1571943--1571950.cif.'
_cod_database_code               1571945
_nottingham_internal_coll_name   REARDC
_nottingham_internal_coll_number 17201
_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   23/08/2017
_nottingham_internal_coll_location NOTTS
_nottingham_internal_coll_instrument 'SN, XDA 017-09'
_nottingham_internal_process_date 17/11/2017
_nottingham_internal_process_user pczwl
_nottingham_internal_solution_date 17/11/2017
_nottingham_internal_solution_user pczwl
_nottingham_internal_refinement_date 17/11/2017
_nottingham_internal_refinement_user pczwl
_nottingham_internal_validation_date 10/2/2018
_nottingham_internal_validation_user pczwl
_nottingham_internal_archive_date 10/2/2018
_shelx_shelxl_version_number     2018/1
_chemical_oxdiff_formula         'C19 H19 Br O'
_chemical_oxdiff_usercomment
'REARDC #17201 SN-1190 IN FOMBLIN FILM ON A MICROMOUNT FOR REA/RD'
_reflns_odcompleteness_completeness 99.81
_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), C17(H17A,H17B), C21(H21A,H21B)
2.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C8(H8), C9(H9), C11(H11), C14(H14), C15(H15), C22(H22)
2.d X=CH2 refined with riding coordinates:
 C23(H23A,H23B)
2.e Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C)
;
_shelx_res_checksum              55227
_shelx_hkl_checksum              60748
_olex2_exptl_crystal_mounting_method "'in fomblin film on a micromount"
_olex2_submission_original_sample_id RA-174-002
_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 1.290
_oxdiff_exptl_absorpt_empirical_full_min 0.817