Enantioselective Ruthenium(II)-Catalyzed Access to Benzonorcaradienes by Coupling of Oxabenzonorbornadienes and Alkynes
Park, Sung Hwan; Wang, Shou-Guo; Cramer, Nicolai; ACS Catalysis  (2019) 10226–; doi:10.1021/acscatal.9b03858

data_4514434
_publ_section_title
;
 Enantioselective Ruthenium(II)-Catalyzed Access to Benzonorcaradienes by
 Coupling of Oxabenzonorbornadienes and Alkynes
;
_journal_name_full               'ACS Catalysis'
_journal_page_first              10226
_journal_paper_doi               10.1021/acscatal.9b03858
_journal_year                    2019
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C14 H14 O3'
_chemical_formula_sum            'C14 H14 O3'
_chemical_formula_weight         230.25
_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   difmap
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.44696(18)
_cell_length_b                   6.98494(19)
_cell_length_c                   23.6748(6)
_cell_measurement_reflns_used    3909
_cell_measurement_temperature    140.00(10)
_cell_measurement_theta_max      75.7780
_cell_measurement_theta_min      7.1260
_cell_volume                     1066.11(5)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'CIFTAB (Sheldrick, 2016)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      140.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2817
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.992
_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     14.00  77.00   1.00    3.00    --   41.04 -99.00-150.00   63
  2  \w     54.00  97.00   1.00    3.00    --   41.04-125.00 -90.00   43
  3  \w      5.00  46.00   1.00    3.00    --   41.04 -99.00-180.00   41
  4  \w     76.00 108.00   1.00   12.00    --  112.00 -94.00-120.00   32
  5  \w     36.00  72.00   1.00   12.00    --  112.00-111.00  30.00   36
  6  \w     48.00 116.00   1.00   12.00    --  112.00-111.00  90.00   68
  7  \w     37.00  94.00   1.00   12.00    --  112.00 -94.00 150.00   57
  8  \w    101.00 159.00   1.00   12.00    --  112.00  30.00 -30.00   58
  9  \w    136.00 162.00   1.00   12.00    --  112.00 111.00-120.00   26
 10  \w    132.00 176.00   1.00   12.00    --  112.00  77.00-150.00   44
 11  \w    102.00 128.00   1.00   12.00    --  112.00 111.00-120.00   26
 12  \w     89.00 170.00   1.00   12.00    --  112.00  77.00 -30.00   81
 13  \w     86.00 112.00   1.00   12.00    --  112.00  77.00-150.00   26
 14  \w     82.00 143.00   1.00   12.00    --  112.00  77.00-180.00   61
 15  \w      1.00  80.00   1.00    3.00    --   41.04 -99.00  30.00   79
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0130
_diffrn_reflns_av_unetI/netI     0.0151
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            4601
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.935
_diffrn_reflns_theta_min         3.734
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.818
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.313
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model.
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.435
_exptl_crystal_description       plate
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.494
_exptl_crystal_size_mid          0.353
_exptl_crystal_size_min          0.146
_refine_diff_density_max         0.218
_refine_diff_density_min         -0.153
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details
;
 Flack x determined using 862 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.05(5)
_refine_ls_extinction_coef       0.0032(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     211
_refine_ls_number_reflns         2193
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.076
_refine_ls_R_factor_all          0.0266
_refine_ls_R_factor_gt           0.0262
_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^)+(0.0427P)^2^+0.2005P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0698
_refine_ls_wR_factor_ref         0.0702
_reflns_Friedel_coverage         0.671
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.983
_reflns_number_gt                2163
_reflns_number_total             2193
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs9b03858_si_002.cif
_cod_data_source_block           shelx
_cod_database_code               4514434
_shelx_shelxl_version_number     2018/3
_shelx_res_checksum              58669
_shelx_hkl_checksum              29269