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_4038615
_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         'C21 H32 O5'
_chemical_formula_sum            'C21 H32 O5'
_chemical_formula_weight         364.46
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2020-06-09
_audit_creation_method
;
Olex2 1.3
(compiled 2019.09.11 svn.r3662 for OlexSys, GUI svn.r5938)
;
_cell_angle_alpha                90
_cell_angle_beta                 100.7770(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.7358(2)
_cell_length_b                   24.4825(3)
_cell_length_c                   7.63190(10)
_cell_measurement_reflns_used    6910
_cell_measurement_temperature    150
_cell_measurement_theta_max      77.1980
_cell_measurement_theta_min      4.5990
_cell_volume                     1787.03(5)
_computing_cell_refinement       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_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 2018/2 (Sheldrick, 2018)'
_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 0.969
_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    -87.00 -35.00   0.50    0.10    --  -46.37 115.00 178.00  104
  2  \w    -84.00 -59.00   0.50    0.30    --  -84.50 115.00 178.00   50
  3  \w    -66.00 -11.00   0.50    0.30    --  -84.50  57.00  30.00  110
  4  \w     57.00  82.00   0.50    0.10    --   46.37 167.00 -37.00   50
  5  \w    100.00 126.00   0.50    0.30    --  108.56 167.00 -37.00   52
  6  \w     73.00  99.00   0.50    0.10    --   46.37 125.00  90.00   52
  7  \w     85.00 117.00   0.50    0.10    --   46.37 125.00 120.00   64
  8  \w     88.00 128.00   0.50    0.30    --  108.56 115.00 178.00   80
  9  \w     31.00 117.00   0.50    0.10    --   46.37  57.00  90.00  172
 10  \w     40.00 123.00   0.50    0.30    --  108.56 -57.00  60.00  166
 11  \w     72.00 104.00   0.50    0.30    --  108.56-115.00  88.00   64
 12  \w     79.00 104.00   0.50    0.30    --  108.56-125.00 150.00   50
 13  \w     37.00  67.00   0.50    0.30    --  108.56-115.00  88.00   60
 14  \w     43.00  73.00   0.50    0.30    --  108.56-125.00 150.00   60
 15  \w     22.00  47.00   0.50    0.10    --   46.37-115.00  88.00   50
 16  \w     40.00  66.00   0.50    0.30    --  108.56 -37.00 120.00   52
 17  \w     35.00  65.00   0.50    0.30    --  108.56 -37.00 150.00   60
 18  \w     38.00  64.00   0.50    0.30    --  108.56 -37.00  30.00   52
 19  \w     49.00  75.00   0.50    0.30    --  108.56 -19.00 -60.00   52
 20  \w     37.00  63.00   0.50    0.30    --  108.56 -37.00 -90.00   52
 21  \w     33.00  75.00   0.50    0.30    --  108.56 -19.00 -90.00   84
 22  \w     43.00  69.00   0.50    0.30    --  108.56 -37.00-120.00   52
 23  \w     40.00  75.00   0.50    0.30    --  108.56 -19.00-150.00   70
 24  \w     35.00  61.00   0.50    0.30    --  108.56 -37.00-150.00   52
 25  \w     32.00 112.00   0.50    0.10    --   46.37  57.00-180.00  160
 26  \w     36.00 116.00   0.50    0.30    --  108.56-125.00-180.00  160
 27  \w    104.00 131.00   0.50    0.30    --  108.56-167.00 -56.00   54
 28  \w    -80.00 -55.00   0.50    0.10    --  -46.37-167.00 -56.00   50
 29  \w   -124.00 -99.00   0.50    0.30    --  -84.50-167.00 -56.00   50
;
_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      -0.1119295000
_diffrn_orient_matrix_UB_12      -0.0423815000
_diffrn_orient_matrix_UB_13      -0.0770944000
_diffrn_orient_matrix_UB_21      -0.0876083000
_diffrn_orient_matrix_UB_22      0.0453460000
_diffrn_orient_matrix_UB_23      -0.1079631000
_diffrn_orient_matrix_UB_31      0.0757984000
_diffrn_orient_matrix_UB_32      -0.0103133000
_diffrn_orient_matrix_UB_33      -0.1569340000
_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  0.0410
_diffrn_reflns_av_unetI/netI     0.0370
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            12821
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.513
_diffrn_reflns_theta_min         3.611
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              PhotonJet-S
_exptl_absorpt_coefficient_mu    0.767
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.524
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.355
_exptl_crystal_description       block
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.332
_exptl_crystal_size_mid          0.215
_exptl_crystal_size_min          0.105
_refine_diff_density_max         0.355
_refine_diff_density_min         -0.290
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         3686
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0519
_refine_ls_R_factor_gt           0.0489
_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^)+(0.0851P)^2^+0.5153P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1359
_refine_ls_wR_factor_ref         0.1391
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3354
_reflns_number_total             3686
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo0c01462_si_002.cif
_cod_data_source_block           20200609n
_cod_database_code               4038615
_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, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9), C12(H12), C14(H14), C19(H19)
2.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C13(H13A,H13B), C7(H7A,H7B), C6(H6A,H6B), C1(H1A,H1B), C2(H2A,
 H2B), C3(H3A,H3B)
2.c Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C20(H20A,H20B,H20C), C21(H21A,H21B,H21C), C17(H17A,H17B,
 H17C)
2.d Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_shelx_res_checksum              24541
_shelx_hkl_checksum              32643
_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 2.155
_oxdiff_exptl_absorpt_empirical_full_min 0.717