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_4518464
_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         'C15 H11 N'
_chemical_formula_sum            'C15 H11 N'
_chemical_formula_weight         205.25
_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
_audit_creation_date             2020-07-31
_audit_creation_method
;
Olex2 1.3
(compiled 2020.07.16 svn.r6f6c53a7 for OlexSys, GUI svn.r6139)
;
_cell_angle_alpha                90
_cell_angle_beta                 112.087(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.3922(6)
_cell_length_b                   8.5924(4)
_cell_length_c                   13.4648(8)
_cell_measurement_reflns_used    5661
_cell_measurement_temperature    98(2)
_cell_measurement_theta_max      29.4150
_cell_measurement_theta_min      2.8690
_cell_volume                     1114.09(12)
_computing_cell_refinement       'CrysAlisPro 1.171.39.28e (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.28e (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.28e (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      98(2)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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    -53.00  94.00   1.00   20.00    --    4.20  11.00  76.00  147
  2  \w    -85.00  26.00   1.00   20.00    --    4.20 -38.00-120.00  111
  3  \w    -97.00  17.00   1.00   20.00    --   -7.70 -38.00  60.00  114
  4  \w    -37.00  -3.00   1.00   20.00    --   -7.70  57.00-180.00   34
  5  \w    -37.00  82.00   1.00   20.00    --   -7.70  57.00  30.00  119
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RCD3): Kappa single'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0705752000
_diffrn_orient_matrix_UB_12      0.0115929000
_diffrn_orient_matrix_UB_13      -0.0336370000
_diffrn_orient_matrix_UB_21      0.0182525000
_diffrn_orient_matrix_UB_22      -0.0026104000
_diffrn_orient_matrix_UB_23      -0.0457082000
_diffrn_orient_matrix_UB_31      -0.0106351000
_diffrn_orient_matrix_UB_32      -0.0816932000
_diffrn_orient_matrix_UB_33      -0.0033560000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0235
_diffrn_reflns_av_unetI/netI     0.0144
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            16726
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.498
_diffrn_reflns_theta_min         2.878
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.071
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90116
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.28e (Rigaku Oxford Diffraction, 2015)
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    1.224
_exptl_crystal_description       plate
_exptl_crystal_F_000             432
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.233
_refine_diff_density_min         -0.174
_refine_diff_density_rms         0.035
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         2296
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.099
_refine_ls_R_factor_all          0.0446
_refine_ls_R_factor_gt           0.0425
_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^)+(0.0365P)^2^+0.5279P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0974
_refine_ls_wR_factor_ref         0.0986
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2201
_reflns_number_total             2296
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs0c05574_si_003.cif
_cod_data_source_block           cd1728
_cod_database_code               4518464
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C20H20N1
_shelx_estimated_absorpt_t_max   0.995
_shelx_estimated_absorpt_t_min   0.965
_reflns_odcompleteness_completeness 99.71
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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:
 C10(H10), C7(H7), C8(H8), C5(H5), C13(H13), C2(H2), C3(H3), C12(H12), C14(H14)
2.b X=CH2 refined with riding coordinates:
 C15(H15A,H15B)
;
_shelx_res_checksum              11588
_shelx_hkl_checksum              77496
_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 1.102
_oxdiff_exptl_absorpt_empirical_full_min 0.925