Experimental and Computational Study of the ( Z)-Selective Formation of Trisubstituted Olefins and Benzo-Fused Oxacycles from the Ruthenium-Catalyzed Dehydrative C-H Coupling of Phenols with Ketones.
Lee, Hanbin; Mane, Manoj V.; Ryu, Ho; Sahu, Debashis; Baik, Mu-Hyun; Yi, Chae S.; Journal of the American Chemical Society 140 (2018) 10289–10296; doi:10.1021/jacs.8b05875

data_4132735
_publ_section_title
;
 Experimental and Computational Study of the ( Z)-Selective Formation of
 Trisubstituted Olefins and Benzo-Fused Oxacycles from the
 Ruthenium-Catalyzed Dehydrative C-H Coupling of Phenols with Ketones.
;
_journal_issue                   32
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              10289
_journal_page_last               10296
_journal_paper_doi               10.1021/jacs.8b05875
_journal_volume                  140
_journal_year                    2018
_chemical_formula_moiety         'C17 H18 O3'
_chemical_formula_sum            'C17 H18 O3'
_chemical_formula_weight         270.31
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2016-09-16
_audit_creation_method
;
Olex2 1.2
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 93.961(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.9036(2)
_cell_length_b                   9.5634(2)
_cell_length_c                   15.2192(4)
_cell_measurement_reflns_used    6228
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      29.0000
_cell_measurement_theta_min      3.4130
_cell_volume                     1438.00(6)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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    'XS (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3756
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.911
_diffrn_measurement_details
;
  1 omega -102.00  -57.00   1.0000    2.1000
omega____ theta____ kappa____ phi______ frames
    -      -11.7478 -178.0000  120.0000 45

  2 omega  -64.00   38.00   1.0000    2.1000
omega____ theta____ kappa____ phi______ frames
    -       11.8259  -37.0000 -120.0000 102

  3 omega  -34.00   93.00   1.0000    2.1000
omega____ theta____ kappa____ phi______ frames
    -       11.8259   19.0000   90.0000 127

  4 omega  -22.00   84.00   1.0000    2.1000
omega____ theta____ kappa____ phi______ frames
    -       11.8259   77.0000 -120.0000 106

  5 omega   35.00  102.00   1.0000    2.1000
omega____ theta____ kappa____ phi______ frames
    -       11.8259  178.0000  150.0000 67
;
_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      -0.0189480000
_diffrn_orient_matrix_UB_12      0.0581333000
_diffrn_orient_matrix_UB_13      0.0253824000
_diffrn_orient_matrix_UB_21      -0.0691537000
_diffrn_orient_matrix_UB_22      -0.0176389000
_diffrn_orient_matrix_UB_23      -0.0087950000
_diffrn_orient_matrix_UB_31      0.0027343000
_diffrn_orient_matrix_UB_32      -0.0425756000
_diffrn_orient_matrix_UB_33      0.0382385000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0346
_diffrn_reflns_av_unetI/netI     0.0323
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            16395
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         29.55
_diffrn_reflns_theta_min         3.31
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77018
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.249
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       irregular
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.51
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.45
_refine_diff_density_max         0.309
_refine_diff_density_min         -0.261
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     185
_refine_ls_number_reflns         3669
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0628
_refine_ls_R_factor_gt           0.0444
_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^)+(0.0480P)^2^+0.5213P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1001
_refine_ls_wR_factor_ref         0.1117
_reflns_number_gt                2877
_reflns_number_total             3669
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja8b05875_si_002.cif
_cod_data_source_block           yi3j
_cod_original_cell_volume        1438.01(6)
_cod_database_code               4132735
_chemical_oxdiff_formula         'C17 H18 O3'
_reflns_odcompleteness_completeness 99.78
_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, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C5(H5), C7(H7), C12(H12), C13(H13), C14(H14), C15(H15), C16(H16)
2.b Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C10(H10A,H10B,H10C), C17(H17A,H17B,H17C)
2.c Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_olex2_submission_special_instructions 'No special instructions were received'