Ruthenium(ii)-catalyzed chemoselective deacylative annulation of 1,3-diones with sulfoxonium ylides via C‒C bond activation
Wen, Si; Lv, Weiwei; Ba, Dan; Liu, Jing; Cheng, Guolin; Chemical Science 10 (2019) 9104–; doi:10.1039/C9SC03245B

data_1555292
_publ_section_title
;
 Ruthenium(ii)-catalyzed chemoselective deacylative annulation of
 1,3-diones with sulfoxonium ylides via C--C bond activation
;
_journal_issue                   39
_journal_name_full               'Chemical Science'
_journal_page_first              9104
_journal_paper_doi               10.1039/C9SC03245B
_journal_volume                  10
_journal_year                    2019
_chemical_formula_moiety         'C18 H13 F3 O2'
_chemical_formula_sum            'C17 H13 F3 O2'
_chemical_formula_weight         318.28
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2019-05-26
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-06-17 deposited with the CCDC.	2019-08-12 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 99.37(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.501(3)
_cell_length_b                   16.731(5)
_cell_length_c                   9.633(2)
_cell_measurement_reflns_used    2277
_cell_measurement_temperature    295.5(2)
_cell_measurement_theta_max      27.5060
_cell_measurement_theta_min      4.0430
_cell_volume                     1510.8(7)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      295.5(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1213
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_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    -34.00  -4.00   1.00    2.97    --  -16.59  38.00 -60.00   30
  2  \w    -23.00  27.00   1.00    2.97    --  -16.59  57.00   0.00   50
  3  \w    -11.00  80.00   1.00    2.97    --   15.81  77.00 150.00   91
  4  \w    -51.00  31.00   1.00    2.97    --   15.81 -57.00 -90.00   82
  5  \w    -16.00  10.00   1.00    2.97    --  -16.59 -99.00 -60.00   26
  6  \w    -17.00  22.00   1.00    2.97    --  -16.59 -99.00-180.00   39
  7  \w    -52.00  43.00   1.00    2.97    --   15.81 -77.00  30.00   95
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0264727000
_diffrn_orient_matrix_UB_12      -0.0239239000
_diffrn_orient_matrix_UB_13      0.0590917000
_diffrn_orient_matrix_UB_21      -0.0632517000
_diffrn_orient_matrix_UB_22      0.0073955000
_diffrn_orient_matrix_UB_23      0.0279963000
_diffrn_orient_matrix_UB_31      -0.0318715000
_diffrn_orient_matrix_UB_32      -0.0343506000
_diffrn_orient_matrix_UB_33      -0.0356123000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1477
_diffrn_reflns_av_unetI/netI     0.1036
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            8734
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         3.71
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.112
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.33697
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.346
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.428
_refine_diff_density_min         -0.637
_refine_diff_density_rms         0.135
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.971
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         2659
_refine_ls_number_restraints     34
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.1319
_refine_ls_R_factor_gt           0.0932
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1760P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2108
_refine_ls_wR_factor_ref         0.2718
_reflns_number_gt                1615
_reflns_number_total             2659
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c9sc03245b2.cif
_cod_data_source_block           exp_6575
_cod_original_sg_symbol_Hall     ' -P 2yn'
_cod_database_code               1555292
_reflns_odcompleteness_completeness 99.59
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C00F-F00K \\sim C00F-F00L \\sim C00F-F00N \\sim F00K-F00L \\sim F00K-F00N
\\sim F00L-F00N
 with sigma of 0.04
 C00M-C00F \\sim C00M-F00K \\sim C00M-F00L \\sim C00M-F00N
 with sigma of 0.02
3. Rigid bond restraints
 C004, C007
 with sigma for 1-2 distances of 0.009 and sigma for 1-3 distances of 0.009
4. Uiso/Uaniso restraints and constraints
C004: within 2A with sigma of 0.02 and sigma for terminal atoms of 0.01
C009: within 2A with sigma of 0.02 and sigma for terminal atoms of 0.04
C004 \\sim C007: within 2A with sigma of 0.001 and sigma for terminal atoms of
0.002
C004 \\sim C009: within 2A with sigma of 0.002 and sigma for terminal atoms of
0.004
5. Others
 Sof(F0AA)=Sof(F00O)=Sof(F00M)=1-FVAR(1)
 Sof(F00K)=Sof(F00L)=Sof(F00N)=FVAR(1)
6.a Aromatic/amide H refined with riding coordinates:
 C007(H007), C008(H008), C00A(H00A), C00B(H00B), C00C(H00C), C00D(H00D),
 C00E(H00E), C00G(H00G), C00H(H00H), C00I(H00I)
6.b Idealised Me refined as rotating group:
 C00J(H00f,H00j,H00k)
;
_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
;
_oxdiff_exptl_absorpt_empirical_full_max 3.354
_oxdiff_exptl_absorpt_empirical_full_min 0.340