Acid-catalysed iterative generation of o-quinone methides for the synthesis of dioxabicyclo[3.3.1]nonanes: total synthesis of myristicyclins A–B
Gharpure, Santosh J.; Jegadeesan, S.; Vishwakarma, Dharmendra S.; Chemical Communications  (2021) –; doi:10.1039/D1CC06146A

data_7129303
_publ_section_title
;
 Acid-catalysed iterative generation of o-quinone methides for the
 synthesis of dioxabicyclo[3.3.1]nonanes: total synthesis of
 myristicyclins A--B
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D1CC06146A
_journal_year                    2021
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C16 H14 O4, H2 O'
_chemical_formula_sum            'C16 H16 O5'
_chemical_formula_weight         288.29
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_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.	2021-11-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.3663(2)
_cell_length_b                   7.4309(3)
_cell_length_c                   32.7640(14)
_cell_measurement_reflns_used    2496
_cell_measurement_temperature    150
_cell_measurement_theta_max      72.3130
_cell_measurement_theta_min      2.6520
_cell_volume                     1306.51(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_area_resol_mean 28.5714
_diffrn_detector_type            'Rigaku Saturn724+'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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   -169.00 -38.00   1.00   12.00    -- -101.00   0.00 108.00  131
  2  \w   -107.00   0.00   1.00   12.00    --  -32.00 -72.00 -36.00  107
  3  \w    -97.00 -37.00   1.00   12.00    -- -101.00  72.00 108.00   60
  4  \w    -88.00 -34.00   1.00   12.00    -- -101.00  72.00  36.00   54
  5  \w   -153.00 -96.00   1.00   12.00    -- -101.00 -72.00-180.00   57
  6  \w   -122.00 -92.00   1.00   12.00    --  -32.00   0.00-180.00   30
  7  \w   -173.00 -67.00   1.00   12.00    -- -101.00 -72.00  36.00  106
  8  \w   -109.00 -25.00   1.00   12.00    -- -101.00   0.00-180.00   84
  9  \w    -37.00  58.00   1.00   12.00    --  -32.00  72.00 108.00   95
 10  \w   -128.00 -96.00   1.00   12.00    -- -101.00  72.00-180.00   32
 11  \w   -191.00-144.00   1.00   12.00    -- -101.00 -72.00-108.00   47
;
_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_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0973
_diffrn_reflns_av_unetI/netI     0.0908
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            6690
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        64.994
_diffrn_reflns_theta_max         64.994
_diffrn_reflns_theta_min         2.697
_exptl_absorpt_coefficient_mu    0.909
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.52838
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
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    1.466
_exptl_crystal_description       plate
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.198
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.036
_refine_diff_density_max         0.236
_refine_diff_density_min         -0.302
_refine_diff_density_rms         0.075
_refine_ls_abs_structure_details
;
 Flack x determined using 576 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.4(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     196
_refine_ls_number_reflns         2219
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.0708
_refine_ls_R_factor_gt           0.0534
_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^)+(0.0677P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1239
_refine_ls_wR_factor_ref         0.1347
_reflns_Friedel_coverage         0.641
_reflns_Friedel_fraction_full    0.986
_reflns_Friedel_fraction_max     0.986
_reflns_number_gt                1825
_reflns_number_total             2219
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1cc06146a2.cif
_cod_data_source_block           sjg-jsm-05-47_cu
_cod_original_cell_volume        1306.52(10)
_cod_database_code               7129303
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.968
_shelx_estimated_absorpt_t_min   0.841
_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, All O(H) groups, All O(H,H) groups
2.a Free rotating group:
 O5(H5A,H5B)
2.b Ternary CH refined with riding coordinates:
 C4(H4A)
2.c Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B)
2.d Aromatic/amide H refined with riding coordinates:
 C9(H9), C15(H15), C7(H7), C12(H12), C13(H13), C14(H14)
2.e Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
2.f Idealised tetrahedral OH refined as rotating group:
 O4(H4), O3(H3)
;
_shelx_res_checksum              52901
_shelx_hkl_checksum              65563
_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
;