Merging π-Acid and Pd Catalysis: Dearomatizing Spirocyclization/Cross-Coupling Cascade Reactions of Alkyne-Tethered Aromatics
Ho, Hon Eong; Stephens, Thomas C.; Payne, Thomas J.; O’Brien, Peter; Taylor, Richard J. K.; Unsworth, William P.; ACS Catalysis 9 (2018) 504–; doi:10.1021/acscatal.8b03861

data_4515473
_publ_section_title
;
 Merging \p-Acid and Pd Catalysis: Dearomatizing
 Spirocyclization/Cross-Coupling Cascade Reactions of Alkyne-Tethered
 Aromatics
;
_journal_issue                   1
_journal_name_full               'ACS Catalysis'
_journal_page_first              504
_journal_paper_doi               10.1021/acscatal.8b03861
_journal_volume                  9
_journal_year                    2018
_chemical_formula_moiety         'C20 H23 N O2'
_chemical_formula_sum            'C20 H23 N O2'
_chemical_formula_weight         309.39
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2018-11-29
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   13.7600(3)
_cell_length_b                   7.1297(2)
_cell_length_c                   34.2631(7)
_cell_measurement_reflns_used    3826
_cell_measurement_temperature    110.00(14)
_cell_measurement_theta_max      70.6360
_cell_measurement_theta_min      4.1110
_cell_volume                     3361.37(14)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      110.00(14)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1450
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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    -29.00  48.00   1.00   18.00    --    0.00  77.00 -30.00   77
  2  \w     34.00  65.00   1.00   18.00    --    0.00  57.00-120.00   31
  3  \w     17.00  69.00   1.00   73.50    --   54.00 -57.00-150.00   52
  4  \w     40.00  80.00   1.00   73.50    --   54.00 -77.00 150.00   40
  5  \w     29.00 118.00   1.00   73.50    --   54.00  37.00-150.00   89
  6  \w    -12.00  79.00   1.00   73.50    --   54.00 -37.00  30.00   91
  7  \w     39.00 133.00   1.00   75.00    --  108.00 -37.00-150.00   94
  8  \w     49.00 103.00   1.00   75.00    --  108.00-111.00-120.00   54
  9  \w     41.00 138.00   1.00   75.00    --  108.00 -77.00-120.00   97
 10  \w    105.00 130.00   1.00   75.00    --  108.00 111.00 120.00   25
 11  \w     92.00 175.00   1.00   75.00    --  108.00  63.00   0.00   83
 12  \w    141.00 166.00   1.00   75.00    --  108.00 111.00-180.00   25
 13  \w    100.00 126.00   1.00   75.00    --  108.00 111.00-180.00   26
 14  \w     77.00 134.00   1.00   75.00    --  108.00 -25.00   0.00   57
 15  \w     41.00  71.00   1.00   75.00    --  108.00 -25.00   0.00   30
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0086882000
_diffrn_orient_matrix_UB_12      -0.1060971000
_diffrn_orient_matrix_UB_13      -0.0390140000
_diffrn_orient_matrix_UB_21      -0.0164899000
_diffrn_orient_matrix_UB_22      0.1871737000
_diffrn_orient_matrix_UB_23      -0.0214562000
_diffrn_orient_matrix_UB_31      0.1103940000
_diffrn_orient_matrix_UB_32      0.0197303000
_diffrn_orient_matrix_UB_33      -0.0063000000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0371
_diffrn_reflns_av_unetI/netI     0.0306
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_number            11243
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.026
_diffrn_reflns_theta_max         67.026
_diffrn_reflns_theta_min         4.121
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.617
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.684
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
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    1.223
_exptl_crystal_description       block
_exptl_crystal_F_000             1328
_exptl_crystal_size_max          0.214
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.042
_refine_diff_density_max         0.248
_refine_diff_density_min         -0.212
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         3010
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0592
_refine_ls_R_factor_gt           0.0479
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0574P)^2^+1.5673P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1173
_refine_ls_wR_factor_ref         0.1251
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2467
_reflns_number_total             3010
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs8b03861_si_003.cif
_cod_data_source_block           wpu1802
_cod_database_code               4515473
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C11 H10 N O'
_chemical_oxdiff_usercomment     'Hon Eong, Ho heh460'
_reflns_odcompleteness_completeness 99.91
_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
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C12(H12)
2.b Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B), C14(H14A,H14B), C13(H13A,H13B)
2.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C1(H1), C2(H2A), C4(H4)
2.d Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C15(H15A,H15B,H15C), C18(H18A,H18B,H18C)
2.e Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_shelx_res_checksum              34268
_shelx_hkl_checksum              96690
_olex2_date_sample_data_collection 2018-04-06
_olex2_date_sample_submission    2018-03-27
_olex2_exptl_crystal_mounting_method 'oil on micromount '
_olex2_submission_original_sample_id 'Hon Eong Ho heh460'
_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 3.864
_oxdiff_exptl_absorpt_empirical_full_min 0.571