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_7061311
_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 H26 O5'
_chemical_formula_sum            'C25 H26 O5'
_chemical_formula_weight         406.45
_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
_audit_creation_date             2021-06-17
_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                101.064(6)
_cell_angle_beta                 106.529(6)
_cell_angle_gamma                104.988(6)
_cell_formula_units_Z            2
_cell_length_a                   9.1365(7)
_cell_length_b                   10.0584(7)
_cell_length_c                   13.1688(9)
_cell_measurement_reflns_used    2652
_cell_measurement_temperature    150
_cell_measurement_theta_max      29.7390
_cell_measurement_theta_min      2.1940
_cell_volume                     1073.67(15)
_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_measured_fraction_theta_full 0.984
_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   -110.00  70.00   0.50    8.00    --  -20.00   0.00 -36.00  360
  2  \w    -71.00  19.00   0.50    8.00    --  -20.00 -72.00 108.00  180
  3  \w    -69.00  -1.00   0.50    8.00    --  -20.00 -72.00 -36.00  136
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type
'dtrek-CrysAlisPro-abstract goniometer imported rigaku-d*trek images'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0559
_diffrn_reflns_av_unetI/netI     0.0946
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.984
_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       15
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            6967
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        24.996
_diffrn_reflns_theta_max         24.996
_diffrn_reflns_theta_min         2.188
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77779
_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    1.257
_exptl_crystal_description       block
_exptl_crystal_F_000             432
_exptl_crystal_size_max          0.205
_exptl_crystal_size_mid          0.136
_exptl_crystal_size_min          0.052
_refine_diff_density_max         0.711
_refine_diff_density_min         -0.523
_refine_diff_density_rms         0.106
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     275
_refine_ls_number_reflns         3720
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.1183
_refine_ls_R_factor_gt           0.0743
_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^)+(0.1023P)^2^+0.2519P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1782
_refine_ls_wR_factor_ref         0.2269
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2308
_reflns_number_total             3720
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2nj00244b2.cif
_cod_data_source_block           sjg-jsm-06-40_mo
_cod_depositor_comments
;
Adding full bibliography for 7061308--7061314.cif.

2025-03-04
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_weight         162.58
_cod_original_formula_moiety         '0.4(C25 H26 O5)'
_cod_original_formula_units_Z            5
_cod_original_cell_volume        1073.67(14)
_cod_original_formula_sum        'C10 H10.40 O2'
_cod_database_code               7061311
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.995
_shelx_estimated_absorpt_t_min   0.982
_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:
 C00M(H00M), C00R(H00R)
2.b Secondary CH2 refined with riding coordinates:
 C00Q(H00L,H00N)
2.c Aromatic/amide H refined with riding coordinates:
 C008(H008), C009(H009), C00C(H00C), C00D(H00D), C00E(H00E), C00H(H00H),
 C00J(H00K), C00O(H00O), C00P(H00P), C00S(H00S)
2.d Idealised Me refined as rotating group:
 C00G(H00A,H00B,H00F), C00I(H00G,H00I,H00J), C00T(H00Q,H00T,H00U), C00U(H00V,
 H00W,H00X)
;
_shelx_res_checksum              35941
_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
;