Olefination with Sulfonyl Halides and Esters: Scope, Limitations, and Mechanistic Studies of the Hawkins Reaction
Górski, Bartosz; Talko, Alicja; Basak, Tymoteusz; Barbasiewicz, Michał; Organic Letters  (2017) –; doi:10.1021/acs.orglett.7b00517

data_1545582
_publ_section_title
;
 Olefination with Sulfonyl Halides and Esters: Scope, Limitations, and
 Mechanistic Studies of the Hawkins Reaction
;
_journal_name_full               'Organic Letters'
_journal_paper_doi               10.1021/acs.orglett.7b00517
_journal_year                    2017
_chemical_formula_moiety         'C19 H24 O4 S'
_chemical_formula_sum            'C19 H24 O4 S'
_chemical_formula_weight         348.44
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_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_date             2016-11-22
_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                 117.0978(17)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   12.79080(18)
_cell_length_b                   23.3516(2)
_cell_length_c                   13.99502(19)
_cell_measurement_reflns_used    19523
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      76.7360
_cell_measurement_theta_min      3.7800
_cell_volume                     3721.26(10)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XLMP (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4391
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0329149000
_diffrn_orient_matrix_UB_12      0.0633336000
_diffrn_orient_matrix_UB_13      -0.0016784000
_diffrn_orient_matrix_UB_21      0.1229215000
_diffrn_orient_matrix_UB_22      -0.0115159000
_diffrn_orient_matrix_UB_23      0.0930336000
_diffrn_orient_matrix_UB_31      0.0459807000
_diffrn_orient_matrix_UB_32      -0.0144974000
_diffrn_orient_matrix_UB_33      -0.0814698000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0385
_diffrn_reflns_av_unetI/netI     0.0210
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            37028
_diffrn_reflns_theta_full        74.50
_diffrn_reflns_theta_max         74.50
_diffrn_reflns_theta_min         3.79
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.700
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.71961
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.244
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1488
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.433
_refine_diff_density_min         -0.517
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     445
_refine_ls_number_reflns         7521
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0385
_refine_ls_R_factor_gt           0.0358
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0515P)^2^+1.7318P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0963
_refine_ls_wR_factor_ref         0.0988
_reflns_number_gt                6967
_reflns_number_total             7521
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol7b00517_si_002.cif
_cod_data_source_block           mb-590f
_cod_depositor_comments
;

2019-02-18
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_cell_volume        3721.25(8)
_cod_original_formula_moiety     '2(C19 H24 O4 S)'
_cod_original_formula_sum        'C38 H48 O8 S2'
_cod_original_formula_units_Z    4
_cod_original_formula_weight     696.88
_cod_database_code               1545582
_chemical_oxdiff_formula         ' C19 H24 O4 S '
_chemical_oxdiff_usercomment     '100 K, colourless plate'
_reflns_odcompleteness_completeness 98.92
_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, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C7A(H7A), C7B(H7B), C8A(H8A), C8B(H8B)
2.b Secondary CH2 refined with riding coordinates:
 C11A(H11A,H11B), C11B(H11C,H11D)
2.c Aromatic/amide H refined with riding coordinates:
 C2A(H2A), C2B(H2B), C3A(H3A), C3B(H3B), C4A(H4A), C4B(H4B), C5A(H5A),
 C5B(H5B), C6A(H6A), C6B(H6B), C16A(H16A), C16B(H16B), C17A(H17A), C17B(H17B),
 C18A(H18A), C18B(H18B), C19A(H19A), C19B(H19B), C20A(H20A), C20B(H20B)
2.d Idealised Me refined as rotating group:
 C13A(H13A,H13B,H13C), C13B(H13D,H13E,H13F), C23A(H23A,H23B,H23C), C23B(H23D,
 H23E,H23F), C24A(H24A,H24B,H24C), C24B(H24D,H24E,H24F)
;
_olex2_submission_special_instructions 'No special instructions were received'