Enantioselective Medium-Ring Lactone Synthesis through an NHC-Catalyzed Intramolecular Desymmetrization of Prochiral 1,3-Diols
Wu, Zijun; Wang, Jian; ACS Catalysis 7 (2017) 7647–; doi:10.1021/acscatal.7b02302

data_4514232
_publ_section_title
;
 Enantioselective Medium-Ring Lactone Synthesis through an NHC-Catalyzed
 Intramolecular Desymmetrization of Prochiral 1,3-Diols
;
_journal_issue                   11
_journal_name_full               'ACS Catalysis'
_journal_page_first              7647
_journal_paper_doi               10.1021/acscatal.7b02302
_journal_volume                  7
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C26 H26 O6 S'
_chemical_formula_sum            'C26 H26 O6 S'
_chemical_formula_weight         466.53
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2016-07-12
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.2606(6)
_cell_length_b                   7.9157(7)
_cell_length_c                   45.636(5)
_cell_measurement_reflns_used    5321
_cell_measurement_temperature    173
_cell_measurement_theta_max      25.3
_cell_measurement_theta_min      1.8
_cell_volume                     2261.6(4)
_computing_cell_refinement
;
CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)
;
_computing_data_collection
;
CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)
;
_computing_data_reduction
;
CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'CIFTAB (Sheldrick, 2013)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2014)'
_computing_structure_solution    'ShelXT (Sheldrick, 2014)'
_diffrn_ambient_temperature      173
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_details
;
scan:
    Number of images: 360
               Slice: -110.0000 - 70.0000
         Image width: 0.5000
            Exp time: 10.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 45.0000
                 Phi: 270.0000
                 XTD: 55.0464
              2theta: -19.9366
scan:
    Number of images: 270
               Slice: -110.0000 - 25.0000
         Image width: 0.5000
            Exp time: 10.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 45.0000
                 Phi: 180.0000
                 XTD: 55.0464
              2theta: -19.9366
;
_diffrn_measurement_device
;
AFC10: Fixed Chi 2 circle
;
_diffrn_measurement_device_type
;
Rigaku Saturn724+ (2x2 bin mode)
;
_diffrn_measurement_method       'profile data from \w-scans'
_diffrn_measurement_specimen_support Fiber
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      0.149045
_diffrn_orient_matrix_UB_12      -0.041206
_diffrn_orient_matrix_UB_13      -0.040014
_diffrn_orient_matrix_UB_21      -0.002262
_diffrn_orient_matrix_UB_22      0.083689
_diffrn_orient_matrix_UB_23      -0.094607
_diffrn_orient_matrix_UB_31      0.007870
_diffrn_orient_matrix_UB_32      0.015411
_diffrn_orient_matrix_UB_33      0.013444
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0545
_diffrn_reflns_av_unetI/netI     0.0592
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       54
_diffrn_reflns_limit_l_min       -53
_diffrn_reflns_number            11555
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        25.362
_diffrn_reflns_theta_max         25.362
_diffrn_reflns_theta_min         3.132
_diffrn_source                   'Sealed Tube'
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.184
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.764
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.370
_exptl_crystal_density_method    "'not measured'"
_exptl_crystal_description       block
_exptl_crystal_F_000             984
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.223
_refine_diff_density_min         -0.237
_refine_diff_density_rms         0.049
_refine_ls_abs_structure_details
;
 Flack x determined using 1111 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.07(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.150
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     299
_refine_ls_number_reflns         4115
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.150
_refine_ls_R_factor_all          0.0681
_refine_ls_R_factor_gt           0.0606
_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^)+(0.0226P)^2^+1.7990P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1084
_refine_ls_wR_factor_ref         0.1123
_reflns_Friedel_coverage         0.686
_reflns_Friedel_fraction_full    0.982
_reflns_Friedel_fraction_max     0.982
_reflns_number_gt                3752
_reflns_number_total             4115
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs7b02302_si_002.cif
_cod_data_source_block           sa4905d
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'Multi-scan' changed to
'multi-scan' according to
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 

 Adding full bibliography for 4514232.cif.
;
_cod_database_code               4514232
_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 Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C11(H11A,H11B), C12(H12A,H12B), C19(H19A,H19B)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C7(H7), C8(H8), C14(H14), C15(H15), C16(H16), C17(H17),
 C18(H18), C21(H21), C22(H22), C24(H24), C25(H25)
2.c Idealised Me refined as rotating group:
 C26(H26A,H26B,H26C)
;
_shelx_res_checksum              53379
_shelx_hkl_checksum              77388
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'