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_7129306
_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_formula_moiety         'C20 H24 O5'
_chemical_formula_sum            'C20 H24 O5'
_chemical_formula_weight         344.40
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2017-05-01
_audit_creation_method
;
Olex2 1.2-ac3
(compiled 2016.08.26 svn.r3337 for Rigaku Oxford Diffraction, GUI svn.r5221)
;
_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                   7.4157(3)
_cell_length_b                   9.0593(5)
_cell_length_c                   26.5028(14)
_cell_measurement_reflns_used    4731
_cell_measurement_temperature    100
_cell_measurement_theta_max      31.0730
_cell_measurement_theta_min      2.8370
_cell_volume                     1780.49(15)
_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      100
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type            'Rigaku Saturn724+'
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.994
_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   -109.00  67.00   0.50    8.00    --  -20.00   0.00-180.00  352
  2  \w    -26.50  13.50   0.50    8.00    --  -20.00  72.00 108.00   80
;
_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      -0.0098948000
_diffrn_orient_matrix_UB_12      -0.0404584000
_diffrn_orient_matrix_UB_13      0.0227183000
_diffrn_orient_matrix_UB_21      -0.0734800000
_diffrn_orient_matrix_UB_22      0.0456276000
_diffrn_orient_matrix_UB_23      0.0069605000
_diffrn_orient_matrix_UB_31      -0.0601901000
_diffrn_orient_matrix_UB_32      -0.0490201000
_diffrn_orient_matrix_UB_33      -0.0122582000
_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  0.0380
_diffrn_reflns_av_unetI/netI     0.0466
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            7171
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        24.993
_diffrn_reflns_theta_max         24.993
_diffrn_reflns_theta_min         2.724
_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    0.092
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85068
_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    1.285
_exptl_crystal_description       block
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.194
_exptl_crystal_size_min          0.104
_refine_diff_density_max         0.195
_refine_diff_density_min         -0.285
_refine_diff_density_rms         0.055
_refine_ls_abs_structure_details
;
 Flack x determined using 1056 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.0(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     230
_refine_ls_number_reflns         3114
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0478
_refine_ls_R_factor_gt           0.0414
_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^)+(0.0448P)^2^+0.6120P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0961
_refine_ls_wR_factor_ref         0.1007
_reflns_Friedel_coverage         0.713
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                2880
_reflns_number_total             3114
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1cc06146a2.cif
_cod_data_source_block           sjg-jsm-05-95_mo
_cod_depositor_comments
;

2025-03-05
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_weight         172.20
_cod_original_formula_moiety         '0.5(C20 H24 O5)'
_cod_original_formula_units_Z            8
_cod_original_formula_sum        'C10 H12 O2.50'
_cod_database_code               7129306
_reflns_odcompleteness_completeness 93.13
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     30.96
_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:
 C00K(H00O), C00M(H00P)
2.b Secondary CH2 refined with riding coordinates:
 C00D(H00F,H00G), C00J(H00M,H00N)
2.c Aromatic/amide H refined with riding coordinates:
 C006(H006), C009(H009), C00B(H00D), C00C(H00E), C00E(H00H), C00I(H00L)
2.d Idealised Me refined as rotating group:
 C008(H00A,H00B,H00C), C00H(H00I,H00J,H00K), C00N(H00Q,H00R,H00S), C00O(H00T,
 H00U,H00V)
;
_shelx_shelxl_version_number     2014/7
_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 1.293
_oxdiff_exptl_absorpt_empirical_full_min 0.802