Palladium-catalyzed double coupling reaction of terminal alkynes with isocyanides: a direct approach to symmetrical <i>N</i>-aryl dialkynylimines.
Xi, Zhi-Wei; He, Yan; Liu, Li-Qiu; Wang, Ying-Chun; Organic & biomolecular chemistry 18 (2020) 8089–8093; doi:10.1039/d0ob01604g

data_7157723
_publ_section_title
;
 Palladium-catalyzed double coupling reaction of terminal alkynes with
 isocyanides: a direct approach to symmetrical <i>N</i>-aryl
 dialkynylimines.
;
_journal_issue                   40
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              8089
_journal_page_last               8093
_journal_paper_doi               10.1039/d0ob01604g
_journal_volume                  18
_journal_year                    2020
_chemical_formula_moiety         'C23 H40 N2 O'
_chemical_formula_sum            'C23 H40 N2 O'
_chemical_formula_weight         360.57
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2019-07-24
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-09-16 deposited with the CCDC.	2020-09-29 downloaded from the CCDC.
;
_cell_angle_alpha                79.118(6)
_cell_angle_beta                 88.843(6)
_cell_angle_gamma                68.605(6)
_cell_formula_units_Z            2
_cell_length_a                   8.2053(5)
_cell_length_b                   9.9516(6)
_cell_length_c                   14.8729(13)
_cell_measurement_reflns_used    2977
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      28.8120
_cell_measurement_theta_min      2.7810
_cell_volume                     1108.86(15)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_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_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_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    -59.00  35.00   1.00    4.00    --   11.74 -57.00-180.00   94
  2  \w    -16.00  75.00   1.00    4.00    --   11.74  77.00  90.00   91
  3  \w    -15.00  81.00   1.00    4.00    --   11.74  57.00 -30.00   96
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0073454000
_diffrn_orient_matrix_UB_12      0.0095680000
_diffrn_orient_matrix_UB_13      0.0456110000
_diffrn_orient_matrix_UB_21      0.0177242000
_diffrn_orient_matrix_UB_22      0.0646309000
_diffrn_orient_matrix_UB_23      -0.0167292000
_diffrn_orient_matrix_UB_31      -0.0909727000
_diffrn_orient_matrix_UB_32      0.0426914000
_diffrn_orient_matrix_UB_33      -0.0022229000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0277
_diffrn_reflns_av_unetI/netI     0.0522
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            7160
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         2.241
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.065
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83488
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
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    1.080
_exptl_crystal_description       block
_exptl_crystal_F_000             400
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.230
_refine_diff_density_min         -0.236
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         3897
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0654
_refine_ls_R_factor_gt           0.0497
_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^)+(0.0390P)^2^+0.4368P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1070
_refine_ls_wR_factor_ref         0.1161
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3091
_reflns_number_total             3897
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ob01604g2.cif
_cod_data_source_block           xzw-32
_cod_depositor_comments
'Adding full bibliography for 7157722--7157724.cif.'
_cod_original_cell_volume        1108.87(14)
_cod_database_code               7157723
_shelx_shelxl_version_number     2018/3
_reflns_odcompleteness_completeness 99.96
_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
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C13(H13)
2.b Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B), C8(H8A,H8B), C14(H14A,H14B), C15(H15A,H15B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2)
2.d Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C), C23(H23A,H23B,H23C), C11(H11A,H11B,H11C), C19(H19A,H19B,
 H19C), C10(H10A,H10B,H10C), C20(H20A,H20B,H20C), C7(H7A,H7B,H7C), C12(H12A,
 H12B,H12C), C6(H6A,H6B,H6C), C21(H21A,H21B,H21C)
;
_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 1.353
_oxdiff_exptl_absorpt_empirical_full_min 0.579