Formal Total Synthesis of Atropurpuran.
Suzuki, Takahiro; Koyama, Takeshi; Nakanishi, Kenta; Kobayashi, Susumu; Tanino, Keiji; The Journal of organic chemistry  (2020) –; doi:10.1021/acs.joc.0c01462

data_4038614
_publ_section_title
;
 Formal Total Synthesis of Atropurpuran.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.0c01462
_journal_year                    2020
_chemical_formula_moiety         'C20 H24 O5'
_chemical_formula_sum            'C20 H24 O5'
_chemical_formula_weight         344.39
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-12-10
_audit_creation_method
;
Olex2 1.3
(compiled 2019.09.11 svn.r3662 for OlexSys, GUI svn.r5938)
;
_cell_angle_alpha                90
_cell_angle_beta                 96.7500(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.48940(10)
_cell_length_b                   6.98630(10)
_cell_length_c                   18.0570(2)
_cell_measurement_reflns_used    8280
_cell_measurement_temperature    150
_cell_measurement_theta_max      76.9880
_cell_measurement_theta_min      3.8550
_cell_volume                     1689.91(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 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      150
_diffrn_detector                 'Rigaku HyPix-6000 area detector'
_diffrn_detector_area_resol_mean 10.0
_diffrn_detector_type            'HPC area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_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   -121.00 -30.00   0.50    0.05    --  -46.37 -18.00  25.00  182
  2  \w    -50.00 -11.00   0.50    0.15    --  -84.50  37.00 -30.00   78
  3  \w    -76.00 -51.00   0.50    0.15    --  -84.50  18.00-165.00   50
  4  \w    -49.00 -11.00   0.50    0.15    --  -84.50  18.00-165.00   76
  5  \w    -45.00 -15.00   0.50    0.05    --  -46.37  18.00-165.00   60
  6  \w     33.00 105.00   0.50    0.05    --   46.37  18.00-165.00  144
  7  \w     95.00 178.00   0.50    0.15    --  108.56  18.00-165.00  166
  8  \w     80.00 112.00   0.50    0.15    --  108.56-125.00  30.00   64
  9  \w     72.00  98.00   0.50    0.15    --  108.56 -99.00 -90.00   52
 10  \w     44.00  76.00   0.50    0.15    --  108.56 -19.00-120.00   64
 11  \w     38.00  69.00   0.50    0.15    --  108.56 -37.00-150.00   62
 12  \w     40.00  69.00   0.50    0.15    --  108.56 -37.00-180.00   58
 13  \w     10.00  87.00   0.50    0.05    --   46.37-125.00-120.00  154
 14  \w     36.00 108.00   0.50    0.15    --  108.56 -99.00 -60.00  144
 15  \w     46.00  72.00   0.50    0.15    --  108.56 -18.00  25.00   52
 16  \w     35.00  72.00   0.50    0.15    --  108.56 -19.00   0.00   74
 17  \w     35.00  69.00   0.50    0.15    --  108.56 -37.00 -60.00   68
 18  \w     38.00  98.00   0.50    0.15    --  108.56 -99.00  30.00  120
 19  \w     37.00  78.00   0.50    0.15    --  108.56 -99.00 150.00   82
 20  \w     82.00 108.00   0.50    0.15    --  108.56 -99.00 150.00   52
 21  \w     39.00  64.00   0.50    0.15    --  108.56-125.00  30.00   50
 22  \w     41.00  66.00   0.50    0.15    --  108.56 -37.00  60.00   50
 23  \w     18.00  43.00   0.50    0.05    --   46.37 -18.00  25.00   50
 24  \w   -138.00-113.00   0.50    0.15    --  -84.50 -18.00  25.00   50
 25  \w   -156.00 -86.00   0.50    0.15    --  -84.50 -99.00-180.00  140
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku XtaLAB Synergy-S'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0642288000
_diffrn_orient_matrix_UB_12      0.0180527000
_diffrn_orient_matrix_UB_13      -0.0760732000
_diffrn_orient_matrix_UB_21      -0.0939851000
_diffrn_orient_matrix_UB_22      -0.0490787000
_diffrn_orient_matrix_UB_23      0.0370585000
_diffrn_orient_matrix_UB_31      -0.0161114000
_diffrn_orient_matrix_UB_32      0.2142691000
_diffrn_orient_matrix_UB_33      0.0148951000
_diffrn_radiation_monochromator  'multi-layer mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0302
_diffrn_reflns_av_unetI/netI     0.0261
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -3
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            11886
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.230
_diffrn_reflns_theta_min         3.880
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              PhotonJet-S
_exptl_absorpt_coefficient_mu    0.789
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.424
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.354
_exptl_crystal_description       plate
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.487
_exptl_crystal_size_mid          0.366
_exptl_crystal_size_min          0.108
_refine_diff_density_max         0.172
_refine_diff_density_min         -0.304
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         3092
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.099
_refine_ls_R_factor_all          0.0425
_refine_ls_R_factor_gt           0.0402
_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^)+(0.0612P)^2^+0.4315P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1080
_refine_ls_wR_factor_ref         0.1100
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2842
_reflns_number_total             3092
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo0c01462_si_004.cif
_cod_data_source_block           20191016
_cod_database_code               4038614
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H O'
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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), C14(H14), C12(H12), C4(H4)
2.b Secondary CH2 refined with riding coordinates:
 C6(H6a,H6b), C11(H11a,H11b), C7(H7a,H7b), C13(H13a,H13b), C3(H3a,H3b), C2(H2a,
 H2b)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C17(H17)
2.d Idealised Me refined as rotating group:
 C19(H19a,H19b,H19c), C20(H20a,H20b,H20c)
;
_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
;
_oxdiff_exptl_absorpt_empirical_full_max 1.300
_oxdiff_exptl_absorpt_empirical_full_min 0.524