Total synthesis of myristinins A–F and 3′-hydroxy-5,7-dimethoxy-4-O-2′-cycloflavan by iterative generation of o-quinone methides
Gharpure, Santosh J.; Jegadeesan, S.; Vishwakarma, Dharmendra S.; New Journal of Chemistry 46 (2022) 5460–5463; doi:10.1039/D2NJ00244B

data_7061313
_publ_section_title
;
 Total synthesis of myristinins A--F and
 3&#x2032;-hydroxy-5,7-dimethoxy-4-O-2&#x2032;-cycloflavan by iterative
 generation of o-quinone methides
;
_journal_issue                   12
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              5460
_journal_page_last               5463
_journal_paper_doi               10.1039/D2NJ00244B
_journal_volume                  46
_journal_year                    2022
_chemical_formula_moiety         'C25 H23 Br O6'
_chemical_formula_sum            'C25 H24 Br O6'
_chemical_formula_weight         500.35
_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     dual
_audit_creation_date             2019-01-22
_audit_creation_method
;
Olex2 1.2-ac3
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2021-07-16 deposited with the CCDC.	2022-02-21 downloaded from the CCDC.
;
_cell_angle_alpha                101.354(3)
_cell_angle_beta                 107.907(4)
_cell_angle_gamma                101.361(3)
_cell_formula_units_Z            2
_cell_length_a                   9.1036(4)
_cell_length_b                   9.9813(4)
_cell_length_c                   14.0392(6)
_cell_measurement_reflns_used    5742
_cell_measurement_temperature    150
_cell_measurement_theta_max      30.8720
_cell_measurement_theta_min      2.3500
_cell_volume                     1143.89(9)
_computing_cell_refinement
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_computing_data_collection
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_computing_data_reduction
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      150
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type            'Rigaku Saturn724+'
_diffrn_measured_fraction_theta_full 0.976
_diffrn_measured_fraction_theta_max 0.976
_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   -110.00  70.00   0.50    8.00    --  -20.00   0.00 -36.00  360
  2  \w    -72.00  19.00   0.50    8.00    --  -20.00 -72.00 108.00  182
  3  \w    -69.00 -16.50   0.50    8.00    --  -20.00 -72.00 -36.00  105
;
_diffrn_measurement_device       'AFC12 (Right): Kappa 3 circle'
_diffrn_measurement_device_type  'Rigaku Saturn724+ (2x2 bin mode)'
_diffrn_measurement_method       'profile data from \w-scans'
_diffrn_measurement_specimen_support 'Mitegen 50um'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0328189000
_diffrn_orient_matrix_UB_12      -0.0581369000
_diffrn_orient_matrix_UB_13      -0.0084675000
_diffrn_orient_matrix_UB_21      -0.0342504000
_diffrn_orient_matrix_UB_22      -0.0107828000
_diffrn_orient_matrix_UB_23      -0.0545671000
_diffrn_orient_matrix_UB_31      0.0707626000
_diffrn_orient_matrix_UB_32      0.0468051000
_diffrn_orient_matrix_UB_33      0.0014720000
_diffrn_radiation_collimation    0.3
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0287
_diffrn_reflns_av_unetI/netI     0.0433
_diffrn_reflns_Laue_measured_fraction_full 0.976
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            7129
_diffrn_reflns_point_group_measured_fraction_full 0.976
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        24.996
_diffrn_reflns_theta_max         24.996
_diffrn_reflns_theta_min         2.784
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           24.0
_diffrn_source_power             1.2
_diffrn_source_target            Mo
_diffrn_source_type              'Rotating Anode'
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    1.835
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.44550
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.453
_exptl_crystal_description       block
_exptl_crystal_F_000             514
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.294
_refine_diff_density_min         -0.290
_refine_diff_density_rms         0.071
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     292
_refine_ls_number_reflns         3932
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.002
_refine_ls_R_factor_all          0.0430
_refine_ls_R_factor_gt           0.0344
_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0379P)^2^+0.5256P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0767
_refine_ls_wR_factor_ref         0.0817
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3430
_reflns_number_total             3932
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2nj00244b2.cif
_cod_data_source_block           sjg-jsm-06-35_mo
_cod_depositor_comments
'Adding full bibliography for 7061308--7061314.cif.'
_cod_original_cell_volume        1143.89(8)
_cod_database_code               7061313
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.867
_shelx_estimated_absorpt_t_min   0.734
_reflns_odcompleteness_completeness 84.18
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     30.97
_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:
 C9(H9), C17(H17)
2.b Secondary CH2 refined with riding coordinates:
 C18(H18A,H18B), C25(H25A,H25B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C20(H20), C24(H24), C23(H23), C15(H15), C14(H14), C12(H12), C5(H5)
2.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C10(H10A,H10B,H10C), C8(H8A,H8B,H8C)
;
_shelx_res_checksum              28246
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.756
_oxdiff_exptl_absorpt_empirical_full_min 0.583