Total synthesis of kingianin a.
Lim, Hee Nam; Parker, Kathlyn A.; Organic letters 15 (2013) 398–401; doi:10.1021/ol303388k

data_1508888
_publ_section_title
;
 Total synthesis of kingianin a.
;
_journal_issue                   2
_journal_name_full               'Organic letters'
_journal_page_first              398
_journal_page_last               401
_journal_paper_doi               10.1021/ol303388k
_journal_volume                  15
_journal_year                    2013
_chemical_formula_moiety         'C40 H42 O8'
_chemical_formula_sum            'C40 H42 O8'
_chemical_formula_weight         650.74
_chemical_melting_point          164.5(5)
_chemical_name_common            'tethered kingianin precursor'
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET)
(compiled Aug 27 2010,11:50:40)
;
_cell_angle_alpha                90.0
_cell_angle_beta                 104.021(9)
_cell_angle_gamma                90.0
_cell_formula_units_Z            4
_cell_length_a                   7.2612(5)
_cell_length_b                   46.730(4)
_cell_length_c                   9.8379(8)
_cell_measurement_reflns_used    2637
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      73.5407
_cell_measurement_theta_min      3.7805
_cell_volume                     3238.7(5)
_computing_cell_refinement
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET)
(compiled Aug 27 2010,11:50:40)
;
_computing_data_collection
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET)
(compiled Aug 27 2010,11:50:40)
;
_computing_data_reduction
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET)
(compiled Aug 27 2010,11:50:40)
;
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 10.4962
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_details
;
  1 omega -113.00  -18.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.1947  -37.0000 -150.0000 95

  2 omega   43.00   95.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       40.1947 -125.0000   90.0000 52

  3 omega  -36.00   22.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       40.1947  -37.0000  -60.0000 58

  4 omega   14.00   47.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       40.1947   37.0000 -120.0000 33

  5 omega   46.00  163.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      106.1167   15.0000 -120.0000 117

  6 omega   90.00  117.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      106.1167  -45.0000 -120.0000 27

  7 omega  100.00  130.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      106.1167  -45.0000  120.0000 30

  8 omega   90.00  116.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      106.1167  -45.0000  -60.0000 26

  9 omega   78.00  150.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      106.1167  179.0000    0.0000 72

 10 omega   68.00  144.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      106.1167  179.0000   60.0000 76

 11 omega   80.00  145.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      106.1167  179.0000  -60.0000 65

 12 omega   91.00  116.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      106.1167  -45.0000   60.0000 25

 13 omega  127.00  152.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      106.1167  111.0000  150.0000 25

 14 omega -119.00   -7.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.1947  -77.0000  -30.0000 112

 15 omega -119.00   -7.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.1947  -77.0000   60.0000 112

 16 omega  -36.00   28.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       40.1947  -37.0000  120.0000 64

 17 omega   79.00  178.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      106.1167   45.0000  -60.0000 99

 18 omega   45.00  178.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      106.1167   15.0000   90.0000 133

;
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0488552000
_diffrn_orient_matrix_UB_12      0.0079336000
_diffrn_orient_matrix_UB_13      -0.1566990000
_diffrn_orient_matrix_UB_21      0.0060451000
_diffrn_orient_matrix_UB_22      0.0319809000
_diffrn_orient_matrix_UB_23      0.0387983000
_diffrn_orient_matrix_UB_31      0.2129952000
_diffrn_orient_matrix_UB_32      0.0009036000
_diffrn_orient_matrix_UB_33      0.0030328000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Cu) X-ray Source'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0899
_diffrn_reflns_av_sigmaI/netI    0.4720
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       57
_diffrn_reflns_limit_k_min       -57
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            22548
_diffrn_reflns_theta_full        73.69
_diffrn_reflns_theta_max         73.5407
_diffrn_reflns_theta_min         3.7805
_exptl_absorpt_coefficient_mu    0.748
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.76985
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET)
(compiled Aug 27 2010,11:50:40)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.335
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1384
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.212
_refine_diff_density_min         -0.170
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       0.00059(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.984
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     434
_refine_ls_number_reflns         6364
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.984
_refine_ls_R_factor_all          0.1911
_refine_ls_R_factor_gt           0.0681
_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^)+(0.0362P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1197
_refine_ls_wR_factor_ref         0.1756
_reflns_number_gt                2402
_reflns_number_total             6364
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol303388k_si_001.cif
_cod_data_source_block           tethered_kingianin_precursor
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '164-165' was changed to '164.5(5)' -
the average value was taken and precision was
estimated.

'_symmetry_cell_setting' value 'Monoclinic' changed to
'monoclinic' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_cell_volume        3238.7(4)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1508888
_reflns_odcompleteness_completeness 99.92
_reflns_odcompleteness_theta     66.97
_reflns_odcompleteness_iscentric 1
_chemical_oxdiff_formula         C40H42O8