Palladium-catalyzed annulation and intermolecular hydroamination involving norbornene derivatives: synthesis of indanones and <i>N</i>-alkylamines.
Li, Wenguang; Cheng, Xinfeng; Cao, Man; Sheng, Heyun; Gao, Wenchao; Chen, Ming; Zhang, Xu; Li, Wentao; Yu, Yongqi; Li, Ting; Chemical communications (Cambridge, England) 60 (2024) 15031–15034; doi:10.1039/d4cc06072e

data_7134000
_publ_section_title
;
 Palladium-catalyzed annulation and intermolecular hydroamination
 involving norbornene derivatives: synthesis of indanones and
 <i>N</i>-alkylamines.
;
_journal_issue                   100
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              15031
_journal_page_last               15034
_journal_paper_doi               10.1039/d4cc06072e
_journal_volume                  60
_journal_year                    2024
_chemical_formula_moiety         'C18 H16 O'
_chemical_formula_sum            'C18 H16 O'
_chemical_formula_weight         248.31
_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
_atom_sites_solution_primary     direct
_audit_creation_date             2024-08-29
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2024-09-10 deposited with the CCDC.	2024-11-22 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.118(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.2395(3)
_cell_length_b                   6.47823(15)
_cell_length_c                   15.3111(3)
_cell_measurement_reflns_used    2160
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.2280
_cell_measurement_theta_min      4.1980
_cell_volume                     1305.73(5)
_computing_cell_refinement       'CrysAlisPro 1.171.42.102a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.102a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.102a (Rigaku OD, 2023)'
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_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   -108.00 -35.00   1.00    1.00    --  -33.50 178.00  60.00   73
  2  \w    -52.00  35.00   1.00    1.00    --  -33.50  57.00-120.00   87
  3  \w    -62.00  27.00   1.00    1.00    --  -33.50  77.00 120.00   89
  4  \w     83.00 109.00   1.00    1.00    --   36.47 178.00-120.00   26
  5  \w     18.00  99.00   1.00    1.00    --   36.47  57.00  90.00   81
  6  \w     36.00  61.00   1.00    1.00    --   36.47 -77.00-180.00   25
  7  \w     79.00 105.00   1.00    1.00    --   36.47 178.00 -30.00   26
  8  \w     -9.00  23.00   1.00    1.00    --   36.47 -77.00-180.00   32
  9  \w     62.00 100.00   1.00    1.00    --   36.47 178.00  60.00   38
 10  \w     38.00  99.00   1.00    5.00    --  108.00 -94.00   0.00   61
 11  \w     46.00 125.00   1.00    5.00    --  108.00 -45.00  30.00   79
 12  \w     42.00  88.00   1.00    5.00    --  108.00-111.00   0.00   46
 13  \w    100.00 126.00   1.00    5.00    --  108.00 -61.00  60.00   26
 14  \w    127.00 167.00   1.00    5.00    --  108.00  77.00 150.00   40
 15  \w    137.00 176.00   1.00    5.00    --  108.00  45.00-150.00   39
 16  \w     96.00 167.00   1.00    5.00    --  108.00  61.00-180.00   71
 17  \w    132.00 178.00   1.00    5.00    --  108.00  45.00 120.00   46
 18  \w     38.00 106.00   1.00    5.00    --  108.00 -94.00  60.00   68
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0366344000
_diffrn_orient_matrix_UB_12      -0.0717385000
_diffrn_orient_matrix_UB_13      -0.0939910000
_diffrn_orient_matrix_UB_21      0.1011631000
_diffrn_orient_matrix_UB_22      0.0718301000
_diffrn_orient_matrix_UB_23      -0.0310910000
_diffrn_orient_matrix_UB_31      0.0460201000
_diffrn_orient_matrix_UB_32      -0.2150342000
_diffrn_orient_matrix_UB_33      0.0210241000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0245
_diffrn_reflns_av_unetI/netI     0.0305
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            4824
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.070
_diffrn_reflns_theta_max         67.070
_diffrn_reflns_theta_min         4.199
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.592
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87951
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.102a (Rigaku Oxford Diffraction, 2023)
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    1.263
_exptl_crystal_description       block
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.140
_refine_diff_density_min         -0.124
_refine_diff_density_rms         0.032
_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-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2334
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0571
_refine_ls_R_factor_gt           0.0445
_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^)+(0.0587P)^2^+0.1236P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1191
_refine_ls_wR_factor_ref         0.1313
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1837
_reflns_number_total             2334
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc06072e3.cif
_cod_data_source_block           202408294_auto
_cod_depositor_comments          'Adding full bibliography for 7134000.cif.'
_cod_database_code               7134000
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C22H21N3O3
_shelx_estimated_absorpt_t_max   0.954
_shelx_estimated_absorpt_t_min   0.911
_reflns_odcompleteness_completeness 99.92
_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 Ternary CH refined with riding coordinates:
 C12(H12), C13(H13), C14(H14), C16(H16)
2.b Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C17(H17A,H17B), C18(H18A,H18B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C7(H7), C10(H10)
;
_shelx_res_checksum              94505
_shelx_hkl_checksum              76923
_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 1.125
_oxdiff_exptl_absorpt_empirical_full_min 0.844