Z-Selective Dienylation Enables Stereodivergent Construction of Dienes and Unravels a Ligand-Driven Mechanistic Dichotomy
Dang, Hang T.; Nguyen, Viet D.; Haug, Graham C.; Vuong, Ngan T. H.; Arman, Hadi D.; Larionov, Oleg V.; ACS Catalysis  (2021) 1042–1052; doi:10.1021/acscatal.0c05574

data_4518465
_publ_section_title
;
 Z-Selective Dienylation Enables Stereodivergent Construction of Dienes
 and Unravels a Ligand-Driven Mechanistic Dichotomy
;
_journal_name_full               'ACS Catalysis'
_journal_page_first              1042
_journal_page_last               1052
_journal_paper_doi               10.1021/acscatal.0c05574
_journal_year                    2021
_chemical_formula_moiety         'C13 H10 O2'
_chemical_formula_sum            'C13 H10 O2'
_chemical_formula_weight         198.21
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2020-11-13
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2019.10.09 svn.r3662 for Rigaku Oxford Diffraction, GUI svn.r5959)
;
_cell_angle_alpha                90
_cell_angle_beta                 108.6879(17)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.8070(2)
_cell_length_b                   11.52820(17)
_cell_length_c                   7.74435(11)
_cell_measurement_reflns_used    6337
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      74.0650
_cell_measurement_theta_min      3.9620
_cell_volume                     998.54(3)
_computing_cell_refinement       'CrysAlisPro 1.171.40.63a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.63a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.63a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT n/a (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.944
_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    -88.00 -14.00   0.50    0.05    --  -46.87 128.00  87.00  148
  2  \w   -120.00 -72.00   0.50    0.05    --  -46.87-128.00  12.00   96
  3  \w   -120.00 -62.00   0.50    0.05    --  -46.87-142.00-158.00  116
  4  \w     36.00  97.00   0.50    0.05    --   46.87-128.00  12.00  122
  5  \w     44.00 105.00   0.50    0.05    --   46.87-142.00-158.00  122
  6  \w   -155.00 -62.00   0.50    0.13    --  -88.50-142.00-158.00  186
  7  \w     36.00 114.00   0.50    0.13    --  106.69-128.00  12.00  156
  8  \w     44.00 124.00   0.50    0.13    --  106.69-142.00-158.00  160
  9  \w     93.00 178.00   0.50    0.13    --  106.69 128.00  87.00  170
 10  \w     84.00 172.00   0.50    0.13    --  106.69 142.00-101.00  176
 11  \w   -120.00 -83.00   0.50    0.05    --  -46.87 -57.00 -90.00   74
 12  \w   -120.00 -83.00   0.50    0.05    --  -46.87 -57.00-180.00   74
 13  \w     83.00 120.00   0.50    0.05    --   46.87  57.00 120.00   74
 14  \w     83.00 120.00   0.50    0.05    --   46.87  57.00-120.00   74
 15  \w    -51.00 -16.00   0.50    0.13    --  -88.50  45.00-120.00   70
 16  \w   -160.00-101.00   0.50    0.13    --  -88.50 -77.00-150.00  118
 17  \w    -71.00 -15.00   0.50    0.13    --  -88.50  61.00-120.00  112
 18  \w   -160.00-100.00   0.50    0.13    --  -88.50 -94.00  60.00  120
 19  \w    -51.00 -16.00   0.50    0.13    --  -88.50  45.00 -30.00   70
 20  \w    -51.00 -16.00   0.50    0.13    --  -88.50  45.00 -90.00   70
 21  \w    -51.00 -16.00   0.50    0.13    --  -88.50  45.00 -60.00   70
 22  \w   -160.00-101.00   0.50    0.13    --  -88.50 -77.00-180.00  118
 23  \w     48.00 130.00   0.50    0.13    --  106.69-150.00 135.78  164
 24  \w     34.00 101.00   0.50    0.13    --  106.69 -77.00-150.00  134
 25  \w     34.00 105.00   0.50    0.13    --  106.69 -94.00  30.00  142
 26  \w     42.00 122.00   0.50    0.13    --  106.69-139.00 155.02  160
 27  \w     32.00  88.00   0.50    0.05    --   46.87  53.00-134.89  112
 28  \w     32.00 120.00   0.50    0.05    --   46.87  48.00  28.53  176
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1037205000
_diffrn_orient_matrix_UB_12      0.0858638000
_diffrn_orient_matrix_UB_13      0.0785939000
_diffrn_orient_matrix_UB_21      -0.0884785000
_diffrn_orient_matrix_UB_22      0.1021980000
_diffrn_orient_matrix_UB_23      -0.0536549000
_diffrn_orient_matrix_UB_31      -0.0193928000
_diffrn_orient_matrix_UB_32      -0.0067746000
_diffrn_orient_matrix_UB_33      0.1872340000
_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  0.0318
_diffrn_reflns_av_unetI/netI     0.0214
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.944
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            11603
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.944
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.475
_diffrn_reflns_theta_min         3.952
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.714
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.738
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.63a (Rigaku Oxford Diffraction, 2019)
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            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.318
_exptl_crystal_description       plank
_exptl_crystal_F_000             416
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.065
_exptl_crystal_size_min          0.048
_refine_diff_density_max         0.233
_refine_diff_density_min         -0.173
_refine_diff_density_rms         0.034
_refine_ls_extinction_coef       0.0036(5)
_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   1.011
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     143
_refine_ls_number_reflns         1979
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.011
_refine_ls_R_factor_all          0.0367
_refine_ls_R_factor_gt           0.0340
_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^)+(0.0438P)^2^+0.3535P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0900
_refine_ls_wR_factor_ref         0.0922
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1817
_reflns_number_total             1979
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs0c05574_si_006.cif
_cod_data_source_block           hpd248
_cod_original_cell_volume        998.53(3)
_cod_database_code               4518465
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H O'
_chemical_oxdiff_usercomment     K638-6
_shelx_estimated_absorpt_t_max   0.967
_shelx_estimated_absorpt_t_min   0.888
_reflns_odcompleteness_completeness 100.00
_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
2.a Aromatic/amide H refined with riding coordinates:
 C6(H6), C8(H8), C2(H2), C5(H5), C10(H10), C3(H3), C12(H12), C11(H11)
;
_shelx_res_checksum              65623
_shelx_hkl_checksum              27796
_olex2_exptl_crystal_mounting_method 'nylon loop'
_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 1.264
_oxdiff_exptl_absorpt_empirical_full_min 0.882