Stereocontrolled Synthesis of (+)-Plagiogyrin A.
Shi, Yunlong; Pierce, Joshua G.; Organic letters 18 (2016) 5308–5311; doi:10.1021/acs.orglett.6b02629

data_1555831
_publ_section_title
;
 Stereocontrolled Synthesis of (+)-Plagiogyrin A.
;
_journal_issue                   20
_journal_name_full               'Organic letters'
_journal_page_first              5308
_journal_page_last               5311
_journal_paper_doi               10.1021/acs.orglett.6b02629
_journal_volume                  18
_journal_year                    2016
_chemical_formula_moiety         'C18 H20 O7'
_chemical_formula_sum            'C18 H20 O7'
_chemical_formula_weight         348.34
_chemical_name_common            YS-88-24
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                69.044(2)
_cell_angle_beta                 81.513(2)
_cell_angle_gamma                81.953(2)
_cell_formula_units_Z            2
_cell_length_a                   8.8256(3)
_cell_length_b                   9.3741(4)
_cell_length_c                   10.7509(4)
_cell_measurement_reflns_used    7994
_cell_measurement_temperature    100.(2)
_cell_measurement_theta_max      30.50
_cell_measurement_theta_min      3.24
_cell_volume                     817.85(6)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100.(2)
_diffrn_detector_area_resol_mean 8.333
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker-Nonius X8 Kappa APEX II'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.035
_diffrn_reflns_av_unetI/netI     0.0301
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            5034
_diffrn_reflns_theta_full        30.63
_diffrn_reflns_theta_max         30.63
_diffrn_reflns_theta_min         2.34
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.109
_exptl_absorpt_correction_T_max  0.746070
_exptl_absorpt_correction_T_min  0.706242
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;

 TWINABS - Bruker AXS scaling for twinned crystals - Version 2012/1
 ------------------------------------------------------------------
 Equivalent reflections defined according to point group -1    
 Reading batch  1 from file rds430_0m.mul
  2 twin components present
 Mean and maximum errors in direction cosine check function =   0.001   0.004
 The mean error should not exceed 0.008, and is usually caused by matrix
 changes during data processing.

 Maximum 2-theta =  61.21 deg.   Approximate wavelength = 0.71075 Angstroms
 Approximate highest resolution = 0.698 Angstroms
 Approximate unit-cell:   8.839   9.388  10.771   69.04   81.54   81.93
 ==============================================================================
 PART 1 - Refinement of parameters to model systematic errors
    11147 data (   3184 unique ) involve domain  1 only,  mean I/sigma  11.9
    11119 data (   3185 unique ) involve domain  2 only,  mean I/sigma   8.7
     6784 data (   2439 unique ) involve   2 domains,  mean I/sigma  11.8
 Settings for parameter refinement:
 Maximum resolution =  0.1000 A
 (Intensity/sigma) threshold = 1.500
 Restraint esd for equal adjacent scale factors =  0.0050
 Maximum odd and even orders for spherical harmonics =   3   6

 Parameter refinement for twin component  1
 ------------------------------------------
    8350 single and      0 composite reflections used for parameter fitting
 Effective data to parameter ratio =    6.26
 wR2(int) =  0.0424 (selected reflections only, before parameter refinement)
 Cycle wR2(incid) wR2(diffr) Mean wt.
    1    0.0400    0.0385    0.9453
    2    0.0378    0.0376    0.9451
...
   39    0.0372    0.0372    0.9447
   40    0.0372    0.0372    0.9447

 wR2(int) =  0.0372 (selected reflections only, after parameter refinement)

 Parameter refinement for twin component  2
 ------------------------------------------
    7571 single and      0 composite reflections used for parameter fitting
 Effective data to parameter ratio =    5.68
 wR2(int) =  0.0486 (selected reflections only, before parameter refinement)
 Cycle wR2(incid) wR2(diffr) Mean wt.
    1    0.0438    0.0420    0.9350
    2    0.0412    0.0410    0.9352
...39    0.0407    0.0407    0.9349
   40    0.0407    0.0407    0.9349
 wR2(int) =  0.0407 (selected reflections only, after parameter refinement)
 ==============================================================================

 PART 2 - Reject outliers and establish error model
 Rejected reflections are ignored in the statistics and Postscript plots
 (except the detector diagnostics) and in the output .hkl files. All statistics
 and error estimates refer to total intensities (of single or composite
 reflections) only. Before applying rejections there are:
   29050 total and   8808 unique reflections assuming Friedel's law.
   29043 total and   8808 unique reflections after rejecting pathological cases 
   29002 total and   8807 unique reflections left after |I-<I>|/su test

 g = 0.0315 gave best error model; g set to 0.0315 for further calculations

 Statistics for singles of twin component  1
 -------------------------------------------
 Scan 2-theta  R(int)  Incid. factors  Diffr. factors    K     Total I>2sig(I)
    1   27.1  0.0250   0.913 - 0.981   0.971 - 1.019   0.675    4486    3595
    2  -55.5  0.0378   0.902 - 0.953   0.972 - 1.018   0.709    1059     800
    3   57.6  0.0390   0.896 - 0.945   0.983 - 1.018   0.676     900     677
    4   47.9  0.0334   0.919 - 0.954   0.995 - 1.019   0.707    1120     857
    5   27.1  0.0263   0.949 - 0.986   0.993 - 1.019   0.675    1149     879
    6   27.1  0.0254   0.932 - 0.969   0.972 - 1.018   0.652    1230    1002
    7   27.1  0.0257   0.890 - 0.930   0.983 - 1.010   0.673    1183     971

   All scans  0.0273   0.890 - 0.986   0.971 - 1.019   0.681   11127    8781

 Statistics for singles of twin component  2
 -------------------------------------------
 Scan 2-theta  R(int)  Incid. factors  Diffr. factors    K     Total I>2sig(I)
    1   27.1  0.0329   0.896 - 0.970   0.973 - 1.023   0.675    4475    3360
    2  -55.5  0.0477   0.863 - 0.916   0.977 - 1.018   0.709    1078     725
    3   57.6  0.0491   0.896 - 0.947   0.981 - 1.022   0.676     893     606
    4   47.9  0.0440   0.896 - 0.939   0.987 - 1.023   0.707    1111     789
    5   27.1  0.0305   0.954 - 0.997   0.988 - 1.023   0.675    1120     799
    6   27.1  0.0331   0.901 - 0.937   0.977 - 1.022   0.652    1240     944
    7   27.1  0.0314   0.896 - 0.971   0.975 - 1.018   0.673    1190     877
   All scans  0.0350   0.863 - 0.997   0.973 - 1.023   0.681   11107    8100

 Statistics for all composite reflections
 ----------------------------------------
 Scan 2-theta  R(int)  Incid. factors  Diffr. factors    K     Total I>2sig(I)
    1   27.1  0.0335   0.904 - 0.975   0.972 - 1.019   0.675    2631    2349
    2  -55.5  0.0436   0.878 - 0.941   0.975 - 1.015   0.709     789     693
    3   57.6  0.0453   0.903 - 0.938   0.983 - 1.017   0.676     656     554
    4   47.9  0.0429   0.910 - 0.940   0.991 - 1.018   0.707     477     420
    5   27.1  0.0339   0.955 - 0.987   0.991 - 1.019   0.675     792     686
    6   27.1  0.0334   0.909 - 0.958   0.976 - 1.016   0.652     745     671
    7   27.1  0.0396   0.898 - 0.958   0.983 - 1.008   0.673     678     596
   All scans  0.0363   0.878 - 0.987   0.972 - 1.019   0.681    6768    5969

 Statistics for all single and composite reflections
 ---------------------------------------------------
 Scan 2-theta  R(int)  Incid. factors  Diffr. factors    K     Total I>2sig(I)
    1   27.1  0.0294   0.896 - 0.981   0.971 - 1.023   0.675   11592    9304
    2  -55.5  0.0423   0.863 - 0.953   0.972 - 1.018   0.709    2926    2218
    3   57.6  0.0437   0.896 - 0.947   0.981 - 1.022   0.676    2449    1837
    4   47.9  0.0387   0.896 - 0.954   0.987 - 1.023   0.707    2708    2066
    5   27.1  0.0296   0.949 - 0.997   0.988 - 1.023   0.675    3061    2364
    6   27.1  0.0296   0.901 - 0.969   0.972 - 1.022   0.652    3215    2617
    7   27.1  0.0306   0.890 - 0.971   0.975 - 1.018   0.673    3051    2444
   All scans  0.0319   0.863 - 0.997   0.971 - 1.023   0.681   29002   22850
 su = K * Sqrt[ sigma^2(I) + (g<I>)^2 ]  where sigma(I) is estimated by SAINT

 The above statistics are based on all non-rejected data, ignoring
 reflections without equivalents when estimating R(int) and K.
 ==============================================================================
 PART 3 - Output Postscript diagnostics and corrected data
 Diagnostic plots written to Postscript file twin.eps
 Blue = component 1, red = 2

 The R(int) and R(sigma) plots are based on all singles and composites,
 <|E^2^-1|> is calculated for all individual contributions from domain 1
 assuming SAINT partitioning and the chi^2^ and spatial plots show only
 those single and composite reflections actually fitted.

 Unique HKLF 4 data extracted from all observed data
 Cycle   N(1) Rint(1)  N(all) Rint(all) Twin fractions
    1   17875  0.0695   28972  0.0638   0.6367  0.3633
    2   17890  0.0502   28997  0.0476   0.6363  0.3637
...19   17890  0.0339   28997  0.0353   0.6347  0.3653
   20   17890  0.0338   28997  0.0353   0.6346  0.3654
 N(1) and Rint(1) refer to singles and composites that include domain 1.
 Rint = 0.0353  for all   28997  observations and
 Rint = 0.0283  for all   16319  observations with I > 3sigma(I)

 Rint is based on agreement between observed single and composite intensities
 and those calculated from refined unique intensities and twin fractions.

    5049 Corrected reflections written to file twin4.hkl
 Reflections merged according to point-group -1    
 Minimum and maximum apparent transmission:  0.705959  0.746070
 Additional spherical absorption correction applied with mu*r =  0.2000

 HKLF 5 dataset constructed from all observations involving domain 1
    7473 Corrected reflections written to file twin5.hkl
 Reflections merged according to point-group -1    
 Single reflections that also occur in composites omitted
 Minimum and maximum apparent transmission:  0.706242  0.746070
 Additional spherical absorption correction applied with mu*r =  0.2000
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.415
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             368
_exptl_crystal_size_max          0.393
_exptl_crystal_size_mid          0.171
_exptl_crystal_size_min          0.117
_refine_diff_density_max         0.472
_refine_diff_density_min         -0.215
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     233
_refine_ls_number_reflns         5034
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0461
_refine_ls_R_factor_gt           0.0370
_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^)+(0.0484P)^2^+0.1648P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0895
_refine_ls_wR_factor_ref         0.0948
_reflns_number_gt                4395
_reflns_number_total             5034
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol6b02629_si_003.cif
_cod_data_source_block           rds430
_cod_database_code               1555831
_shelx_res_checksum              66637
_shelx_hkl_checksum              22113