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_7061314
_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         'C16 H12 O4'
_chemical_formula_sum            'C16 H12 O4'
_chemical_formula_weight         268.25
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-01-22
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2019.04.23 svn.r3594 for Rigaku Oxford Diffraction, GUI svn.r5739)
;
_audit_update_record
;
2021-07-16 deposited with the CCDC.	2022-02-21 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.267(4)
_cell_angle_gamma                90
_cell_formula_units_Z            16
_cell_length_a                   20.0353(7)
_cell_length_b                   7.8785(2)
_cell_length_c                   31.1858(12)
_cell_measurement_reflns_used    5536
_cell_measurement_temperature    150
_cell_measurement_theta_max      72.6450
_cell_measurement_theta_min      2.8200
_cell_volume                     4883.1(3)
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      150
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.999
_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   -191.00 -11.00   1.00    4.00    -- -101.00   0.00 -36.00  180
  2  \w   -122.00  58.00   1.00    4.00    --  -32.00   0.00 -36.00  180
  3  \w   -115.00 -11.00   1.00    4.00    -- -101.00  72.00 108.00  104
  4  \w   -115.00 -11.00   1.00    4.00    -- -101.00  72.00 -36.00  104
  5  \w   -115.00 -15.00   1.00    4.00    -- -101.00  72.00-108.00  100
  6  \w   -111.00 -14.00   1.00    4.00    -- -101.00  72.00-180.00   97
  7  \w   -111.00 -14.00   1.00    4.00    -- -101.00  72.00  36.00   97
  8  \w    -66.00 -15.00   1.00    4.00    --  -32.00  72.00-108.00   51
  9  \w    -51.00 -17.00   1.00    4.00    --  -32.00  72.00  36.00   34
 10  \w   -191.00 -77.00   1.00    4.00    -- -101.00 -72.00 -36.00  114
 11  \w   -191.00 -77.00   1.00    4.00    -- -101.00 -72.00-108.00  114
 12  \w    -36.00  -6.00   1.00    4.00    --  -32.00 -72.00 108.00   30
 13  \w   -189.00-140.00   1.00    4.00    -- -101.00 -72.00-180.00   49
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type
'dtrek-CrysAlisPro-abstract goniometer imported rigaku-d*trek images'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0414176000
_diffrn_orient_matrix_UB_12      0.1266524000
_diffrn_orient_matrix_UB_13      0.0301977000
_diffrn_orient_matrix_UB_21      0.0562594000
_diffrn_orient_matrix_UB_22      -0.0048708000
_diffrn_orient_matrix_UB_23      -0.0294077000
_diffrn_orient_matrix_UB_31      -0.0334851000
_diffrn_orient_matrix_UB_32      0.1489004000
_diffrn_orient_matrix_UB_33      -0.0265647000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.1231
_diffrn_reflns_av_unetI/netI     0.0902
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            20114
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.139
_diffrn_reflns_theta_min         2.857
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.872
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.61685
_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    1.460
_exptl_crystal_description       block
_exptl_crystal_F_000             2240
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.108
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.524
_refine_diff_density_min         -0.607
_refine_diff_density_rms         0.148
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     361
_refine_ls_number_reflns         4792
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.014
_refine_ls_R_factor_all          0.1109
_refine_ls_R_factor_gt           0.0745
_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^)+(0.1812P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2063
_refine_ls_wR_factor_ref         0.2721
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3275
_reflns_number_total             4792
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2nj00244b2.cif
_cod_data_source_block           sjg-dsv-11-56_cu
_cod_depositor_comments
;
Adding full bibliography for 7061308--7061314.cif.

2024-12-16
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C32 H24 O8'
_cod_original_formula_weight         536.51
_cod_original_formula_moiety         '2(C16 H12 O4)'
_cod_original_formula_units_Z            8
_cod_database_code               7061314
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.958
_shelx_estimated_absorpt_t_min   0.880
_reflns_odcompleteness_completeness 97.60
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     72.98
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C00R(H00R), C00U(H00U), C00W(H00W), C00X(H00X)
2.b Secondary CH2 refined with riding coordinates:
 C00V(H00C,H00D), C00Z(H00A,H00B), C012(H01C,H01D), C014(H01A,H01B)
2.c Aromatic/amide H refined with riding coordinates:
 C00F(H00F), C00G(H00G), C00J(H00J), C00M(H00M), C00N(H00N), C00O(H00O),
 C00S(H00S), C00T(H00T), C00Y(H00Y), C010(H010), C011(H011), C013(H013)
;
_shelx_res_checksum              10925
_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 2.517
_oxdiff_exptl_absorpt_empirical_full_min 0.397