Enantioselective total synthesis of colomitides and their absolute configuration determination and structural revision.
Yang, Hongguang; Liu, Xiaoyu; Li, Xiaoyu; Shi, Xiang; Yang, Feilong; Jiao, Xiaozhen; Xie, Ping; Organic & biomolecular chemistry 15 (2017) 3728–3735; doi:10.1039/c7ob00539c

data_7155564
_publ_section_title
;
 Enantioselective total synthesis of colomitides and their absolute
 configuration determination and structural revision.
;
_journal_issue                   17
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              3728
_journal_page_last               3735
_journal_paper_doi               10.1039/c7ob00539c
_journal_volume                  15
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C16 H28 O3 Si'
_chemical_formula_sum            'C16 H28 O3 Si'
_chemical_formula_weight         296.47
_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
_audit_creation_date             2016-12-27
_audit_creation_method
;
  Olex2 1.1
  (compiled 2011.02.15 svn.r1672, GUI svn.r3494)
;
_audit_update_record
;
2017-02-21 deposited with the CCDC.
2017-04-03 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.679(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.9108(3)
_cell_length_b                   9.8191(3)
_cell_length_c                   18.3013(6)
_cell_measurement_reflns_used    5948
_cell_measurement_temperature    104.6
_cell_measurement_theta_max      70.9961
_cell_measurement_theta_min      4.4988
_cell_volume                     1780.23(10)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution
'A short history of SHELX (Sheldrick, 2007)/Bruker'
_diffrn_ambient_temperature      104.6
_diffrn_detector_area_resol_mean 16.0971
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_details
;
  1 omega  -50.00   10.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000  111.0000 -150.0000 60

  2 omega  -20.00   41.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.7919  -37.0000   30.0000 61

  3 omega   49.00  105.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.7919   37.0000  -30.0000 56

  4 omega  -14.00   62.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.7919  -77.0000  120.0000 76

  5 omega   -2.00   52.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.7919  -37.0000 -180.0000 54

  6 omega  -24.00   53.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.7919  -37.0000  -90.0000 77

  7 omega  -29.00   61.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.7919  -77.0000 -180.0000 90

  8 omega   20.00   92.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.7919   65.0000  -97.0000 72

  9 omega   56.00   95.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -150.0000 39

 10 omega  109.00  161.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000  120.0000 52

 11 omega   91.00  124.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000  -30.0000 33

 12 omega  144.00  170.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000  -30.0000 26

 13 omega   88.00  114.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   65.0000  -97.0000 26

 14 omega   81.00  107.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -90.0000 26

 15 omega   71.00   96.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   15.0000  -30.0000 25

 16 omega   40.00   88.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000   30.0000 48

 17 omega  129.00  155.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000 -120.0000 26

 18 omega  131.00  176.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000  150.0000 45

 19 omega   40.00   86.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  -90.0000 46

 20 omega   81.00  107.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -30.0000 26

 21 omega   81.00  107.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -60.0000 26

 22 omega  126.00  173.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -60.0000 47

 23 omega   81.00  107.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000 -120.0000 26

 24 omega   91.00  175.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000 -150.0000 84

 25 omega   73.00   98.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   15.0000    0.0000 25

 26 omega   70.00  102.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   15.0000  -60.0000 32

 27 omega  127.00  171.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -90.0000 44

 28 omega   93.00  156.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000    0.0000 63

 29 omega   77.00  112.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   15.0000   30.0000 35

 30 omega   92.00  117.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   58.0000  -68.0000 25

 31 omega   43.00  126.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000   90.0000 83

 32 omega   95.00  122.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000  -60.0000 27

 33 omega   68.00  140.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -15.0000  150.0000 72
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0662220000
_diffrn_orient_matrix_UB_12      -0.0814514000
_diffrn_orient_matrix_UB_13      0.0613108000
_diffrn_orient_matrix_UB_21      -0.1353160000
_diffrn_orient_matrix_UB_22      0.0722160000
_diffrn_orient_matrix_UB_23      -0.0170881000
_diffrn_orient_matrix_UB_31      -0.0385070000
_diffrn_orient_matrix_UB_32      -0.1128701000
_diffrn_orient_matrix_UB_33      -0.0552079000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0299
_diffrn_reflns_av_unetI/netI     0.0425
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            13060
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.964
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.128
_diffrn_reflns_theta_min         4.835
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.200
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.95477
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.106
_exptl_crystal_description       Block
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.941
_refine_diff_density_min         -0.237
_refine_diff_density_rms         0.070
_refine_ls_abs_structure_details
;
 Flack x determined using 2694 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.03(2)
_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     375
_refine_ls_number_reflns         6632
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.099
_refine_ls_R_factor_all          0.0597
_refine_ls_R_factor_gt           0.0579
_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^)+(0.0869P)^2^+1.2104P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1552
_refine_ls_wR_factor_ref         0.1572
_reflns_Friedel_coverage         0.835
_reflns_Friedel_fraction_full    0.969
_reflns_Friedel_fraction_max     0.936
_reflns_number_gt                6391
_reflns_number_total             6632
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7ob00539c2.cif
_cod_data_source_block           exp_4732
_cod_depositor_comments
'Adding full bibliography for 7155563--7155564.cif.'
_cod_original_cell_volume        1780.22(10)
_cod_database_code               7155564
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_shelx_estimated_absorpt_t_max   0.889
_shelx_estimated_absorpt_t_min   0.795
_shelx_res_checksum              85624
_shelx_shelxl_version_number     2014/7