Synthesis of γ-keto sulfones by copper-catalyzed oxidative sulfonylation of tertiary cyclopropanols
Konik, Yulia A.; Elek, Gabor Zoltan; Kaabel, Sandra; Järving, Ivar; Lopp, Margus; Kananovich, Dzmitry; Org. Biomol. Chem.  (2017) –; doi:10.1039/C7OB01605K

data_7155875
_publ_section_title
;
 Synthesis of \g-keto sulfones by copper-catalyzed oxidative sulfonylation
 of tertiary cyclopropanols
;
_journal_name_full               'Org. Biomol. Chem.'
_journal_paper_doi               10.1039/C7OB01605K
_journal_year                    2017
_chemical_formula_moiety         'C11 H13 F O3 S'
_chemical_formula_sum            'C11 H13 F O3 S'
_chemical_formula_weight         244.27
_chemical_name_systematic
;
4-((fluoromethyl)sulfonyl)-1-phenylbutan-2-one
;
_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     dual
_audit_creation_date             2017-02-20
_audit_creation_method
;
Olex2 1.2
(compiled 2017.01.04 svn.r3372 for OlexSys, GUI svn.r5292)
;
_audit_update_record
;
2017-02-20 deposited with the CCDC.
2017-09-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 115.067(11)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.2903(14)
_cell_length_b                   5.0921(4)
_cell_length_c                   16.0912(14)
_cell_measurement_reflns_used    2882
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      67.0260
_cell_measurement_theta_min      3.1620
_cell_volume                     1134.9(2)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection
;
Rigaku Collection Strategy
(Daniels, L. M. (2011). Acta Cryst. A67, C143)
;
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_molecular_graphics
;
Mercury CSD 3.9 (Macrae, C. F., et al. (2006). J. Appl. Cryst. 39, 453-457)
POV-Ray 3.7 (Persistence of Vision Pty. Ltd. (2004)) 
;
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      123.0
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w   -179.00   0.00   1.00   20.00    --  -90.00  60.00-108.00  179
  2  \w   -110.00  69.00   1.00   10.00    --  -21.00  30.00 -36.00  179
  3  \w   -179.00   0.00   1.00   20.00    --  -90.00  60.00-180.00  179
  4  \w   -179.00   0.00   1.00   20.00    --  -90.00  60.00 -36.00  179
  5  \w   -179.00   0.00   1.00   20.00    --  -90.00  30.00-108.00  179
  6  \w   -179.00   0.00   1.00   20.00    --  -90.00  30.00-180.00  179
  7  \w   -179.00   0.00   1.00   20.00    --  -90.00  30.00 -36.00  179
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku Saturn944+ (2x2 bin mode)'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0077305000
_diffrn_orient_matrix_UB_12      -0.2961120000
_diffrn_orient_matrix_UB_13      -0.0217664000
_diffrn_orient_matrix_UB_21      0.1027948000
_diffrn_orient_matrix_UB_22      -0.0415683000
_diffrn_orient_matrix_UB_23      0.0755020000
_diffrn_orient_matrix_UB_31      -0.0417140000
_diffrn_orient_matrix_UB_32      -0.0466730000
_diffrn_orient_matrix_UB_33      0.0706842000
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0878
_diffrn_reflns_av_unetI/netI     0.0529
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            9604
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        67.402
_diffrn_reflns_theta_max         67.402
_diffrn_reflns_theta_min         3.191
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku MicroMax-003'
_exptl_absorpt_coefficient_mu    2.600
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.53951
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.430
_exptl_crystal_description       block
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.347
_refine_diff_density_min         -0.494
_refine_diff_density_rms         0.076
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         2005
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.084
_refine_ls_R_factor_all          0.0701
_refine_ls_R_factor_gt           0.0562
_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^)+(0.0738P)^2^+0.7657P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1399
_refine_ls_wR_factor_ref         0.1565
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1631
_reflns_number_total             2005
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7ob01605k2.cif
_cod_data_source_block           jk_2
_cod_original_cell_volume        1134.85(19)
_cod_database_code               7155875
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         'C11 H13 O3 S1 F1'
_reflns_odcompleteness_completeness 98.17
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     67.29
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C3(H3A,H3B), C5(H5A,H5B)
2.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C9(H9), C10(H10), C11(H11)
;
_shelx_res_checksum              3988
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 3.036
_oxdiff_exptl_absorpt_empirical_full_min 0.448