Total Synthesis of (+)-Aplykurodinone-1.
Xu, Bo; Xun, Wen; Wang, Tingzhong; Qiu, Fayang G.; Organic letters 19 (2017) 4861–4863; doi:10.1021/acs.orglett.7b02350

data_1547570
_publ_section_title
;
 Total Synthesis of (+)-Aplykurodinone-1.
;
_journal_issue                   18
_journal_name_full               'Organic letters'
_journal_page_first              4861
_journal_page_last               4863
_journal_paper_doi               10.1021/acs.orglett.7b02350
_journal_volume                  19
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C20 H30 O3'
_chemical_formula_sum            'C20 H30 O3'
_chemical_formula_weight         318.44
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2017-05-17
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 95.120(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   10.1944(2)
_cell_length_b                   6.53348(13)
_cell_length_c                   13.5748(3)
_cell_measurement_reflns_used    8046
_cell_measurement_temperature    125(11)
_cell_measurement_theta_max      66.6130
_cell_measurement_theta_min      4.3430
_cell_volume                     900.54(3)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
(compiled Feb  9 2015,16:26:32)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
(compiled Feb  9 2015,16:26:32)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
(compiled Feb  9 2015,16:26:32)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      125(11)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4015
_diffrn_detector_type            Ruby
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
  1 omega    0.00  121.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       41.2882   19.0000   90.0000 121

  2 omega  -33.00   66.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       41.2882  -38.0000   90.0000 99

  3 omega   17.00  116.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       41.2882   38.0000 -180.0000 99

  4 omega   63.00  165.00   1.0000    1.2250
omega____ theta____ kappa____ phi______ frames
    -       92.5000   61.0000  150.0000 102

  5 omega   19.00   96.00   1.0000    1.2250
omega____ theta____ kappa____ phi______ frames
    -       92.5000 -125.0000 -180.0000 77

  6 omega   19.00   77.00   1.0000    1.2250
omega____ theta____ kappa____ phi______ frames
    -       92.5000  -45.0000  150.0000 58

  7 omega   64.00  169.00   1.0000    1.2250
omega____ theta____ kappa____ phi______ frames
    -       92.5000   30.0000  -30.0000 105

  8 omega   16.00   69.00   1.0000    1.2250
omega____ theta____ kappa____ phi______ frames
    -       92.5000  -30.0000   90.0000 53

  9 omega   19.00   96.00   1.0000    1.2250
omega____ theta____ kappa____ phi______ frames
    -       92.5000 -125.0000   60.0000 77

 10 omega   63.00  165.00   1.0000    1.2250
omega____ theta____ kappa____ phi______ frames
    -       92.5000   61.0000 -120.0000 102

 11 omega   10.00   83.00   1.0000    1.2250
omega____ theta____ kappa____ phi______ frames
    -       92.5000  -94.0000  120.0000 73

 12 omega   60.00  169.00   1.0000    1.2250
omega____ theta____ kappa____ phi______ frames
    -       92.5000   77.0000 -180.0000 109

 13 omega   16.00   69.00   1.0000    1.2250
omega____ theta____ kappa____ phi______ frames
    -       92.5000  -30.0000  -60.0000 53

 14 omega    9.00  128.00   1.0000    1.2250
omega____ theta____ kappa____ phi______ frames
    -       92.5000  -87.0000  100.0000 119

 15 omega   16.00   69.00   1.0000    1.2250
omega____ theta____ kappa____ phi______ frames
    -       92.5000  -30.0000 -120.0000 53

 16 omega   10.00   83.00   1.0000    1.2250
omega____ theta____ kappa____ phi______ frames
    -       92.5000  -94.0000 -180.0000 73

 17 omega   20.00  122.00   1.0000    1.2250
omega____ theta____ kappa____ phi______ frames
    -       92.5000  -61.0000    0.0000 102

 18 omega   67.00  166.00   1.0000    1.2250
omega____ theta____ kappa____ phi______ frames
    -       92.5000   45.0000  -90.0000 99

 19 omega   19.00   96.00   1.0000    1.2250
omega____ theta____ kappa____ phi______ frames
    -       92.5000 -125.0000  -60.0000 77

 20 omega   60.00  169.00   1.0000    1.2250
omega____ theta____ kappa____ phi______ frames
    -       92.5000   77.0000    0.0000 109

 21 omega   60.00  169.00   1.0000    1.2250
omega____ theta____ kappa____ phi______ frames
    -       92.5000   77.0000  150.0000 109

 22 omega   60.00  170.00   1.0000    1.2250
omega____ theta____ kappa____ phi______ frames
    -       92.5000   79.0000  126.9895 110

 23 omega   19.00   96.00   1.0000    1.2250
omega____ theta____ kappa____ phi______ frames
    -       92.5000 -125.0000 -120.0000 77

 24 omega   40.00  174.00   1.0000    1.2250
omega____ theta____ kappa____ phi______ frames
    -       92.5000   15.0000   90.0000 134

 25 omega   10.00   83.00   1.0000    1.2250
omega____ theta____ kappa____ phi______ frames
    -       92.5000  -94.0000   60.0000 73

 26 omega   73.00  166.00   1.0000    1.2250
omega____ theta____ kappa____ phi______ frames
    -       92.5000  125.0000 -120.0000 93

 27 omega  -97.00  -18.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.2882  125.0000  -90.0000 79

 28 omega -117.00   -9.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.2882  -77.0000   30.0000 108

 29 omega    9.00  117.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       41.2882   77.0000 -120.0000 108
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Ruby, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0248438000
_diffrn_orient_matrix_UB_12      -0.1976979000
_diffrn_orient_matrix_UB_13      0.0606649000
_diffrn_orient_matrix_UB_21      -0.0966802000
_diffrn_orient_matrix_UB_22      0.0736975000
_diffrn_orient_matrix_UB_23      0.0734533000
_diffrn_orient_matrix_UB_31      -0.1142662000
_diffrn_orient_matrix_UB_32      -0.1052401000
_diffrn_orient_matrix_UB_33      -0.0625260000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0603
_diffrn_reflns_av_unetI/netI     0.0341
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            15746
_diffrn_reflns_theta_full        66.75
_diffrn_reflns_theta_max         66.75
_diffrn_reflns_theta_min         4.35
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'Enhance Ultra (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.606
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.31588
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
(compiled Feb  9 2015,16:26:32)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.174
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             348
_exptl_crystal_size_max          2.0
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.168
_refine_diff_density_min         -0.202
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.2(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     212
_refine_ls_number_reflns         3186
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.071
_refine_ls_R_factor_all          0.0467
_refine_ls_R_factor_gt           0.0419
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0640P)^2^+0.0909P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1050
_refine_ls_wR_factor_ref         0.1101
_reflns_number_gt                2956
_reflns_number_total             3186
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol7b02350_si_002.cif
_cod_data_source_block           exp_895
_cod_database_code               1547570
_reflns_odcompleteness_completeness 99.10
_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:
 C7(H7), C8(H8), C9(H9), C10(H10), C12(H12)
2.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C13(H13A,H13B), C14(H14A,H14B), C16(H16A,H16B), C17(H17A,H17B),
 C19(H19A,H19B)
2.c Aromatic/amide H refined with riding coordinates:
 C22(H22)
2.d Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C20(H20A,H20B,H20C), C21(H21A,H21B,H21C), C23(H23A,H23B,
 H23C)
;
_olex2_date_sample_data_collection 2017-05-16
_olex2_submission_special_instructions 'No special instructions were received'