Aminoarylation of alkynes using diarylanilines.
Liu, Zi; Greaney, Michael F.; Chemical communications (Cambridge, England) 60 (2024) 6296–6299; doi:10.1039/d4cc01935k

data_7133072
_publ_section_title
;
 Aminoarylation of alkynes using diarylanilines.
;
_journal_issue                   49
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              6296
_journal_page_last               6299
_journal_paper_doi               10.1039/d4cc01935k
_journal_volume                  60
_journal_year                    2024
_chemical_formula_moiety         'C19 H20 N2 O4'
_chemical_formula_sum            'C19 H20 N2 O4'
_chemical_formula_weight         340.37
_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   mixed
_audit_creation_date             2023-10-24
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2024-03-21 deposited with the CCDC.	2024-05-21 downloaded from the CCDC.
;
_cell_angle_alpha                77.534(4)
_cell_angle_beta                 79.396(4)
_cell_angle_gamma                80.934(4)
_cell_formula_units_Z            4
_cell_length_a                   8.1324(3)
_cell_length_b                   11.0134(5)
_cell_length_c                   20.2400(8)
_cell_measurement_reflns_used    17862
_cell_measurement_temperature    99.7(7)
_cell_measurement_theta_max      31.2790
_cell_measurement_theta_min      3.5740
_cell_volume                     1726.67(13)
_computing_cell_refinement       'CrysAlisPro 1.171.42.79a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.79a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.79a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.7(7)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0714
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.943
_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    -23.00 101.00   1.00    7.50    --   26.88  19.00   0.00  124
  2  \w      5.00  96.00   1.00    7.50    --   26.88  57.00  30.00   91
  3  \w    -15.00  69.00   1.00    7.50    --   26.88 -99.00-120.00   84
  4  \w    -46.00  54.00   1.00    7.50    --   26.88 -37.00 150.00  100
  5  \w    -15.00  69.00   1.00    7.50    --   26.88 -99.00 120.00   84
  6  \w     -5.00  42.00   1.00    7.50    --   26.88  77.00   0.00   47
  7  \w     37.00 105.00   1.00    7.50    --   26.88-178.00 150.00   68
  8  \w     -5.00  42.00   1.00    7.50    --   26.88  77.00 120.00   47
  9  \w     39.00 105.00   1.00    7.50    --   26.88 178.00  60.00   66
 10  \w     -5.00  42.00   1.00    7.50    --   26.88  77.00 -90.00   47
 11  \w    -46.00  54.00   1.00    7.50    --   26.88 -37.00-120.00  100
 12  \w    -42.00  48.00   1.00    7.50    --   26.88 -57.00  30.00   90
 13  \w      5.00  96.00   1.00    7.50    --   26.88  57.00-180.00   91
 14  \w    -98.00   2.00   1.00    7.50    --  -25.16 -37.00-150.00  100
 15  \w    -42.00   6.00   1.00    7.50    --  -25.16 -77.00-180.00   48
 16  \w    -15.00  69.00   1.00    7.50    --   26.88 -99.00 -30.00   84
 17  \w     37.00 105.00   1.00    7.50    --   26.88-178.00  90.00   68
 18  \w      5.00  96.00   1.00    7.50    --   26.88  57.00 120.00   91
 19  \w     -5.00  42.00   1.00    7.50    --   26.88  77.00 150.00   47
 20  \w    -94.00 -67.00   1.00    7.50    --  -25.16 -57.00  30.00   27
 21  \f     30.00 300.00   1.00    0.50   0.00   0.00   0.00    --   270
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, Eos'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0147264000
_diffrn_orient_matrix_UB_12      0.0628776000
_diffrn_orient_matrix_UB_13      -0.0177112000
_diffrn_orient_matrix_UB_21      0.0453000000
_diffrn_orient_matrix_UB_22      0.0198233000
_diffrn_orient_matrix_UB_23      0.0218202000
_diffrn_orient_matrix_UB_31      0.0758943000
_diffrn_orient_matrix_UB_32      -0.0092743000
_diffrn_orient_matrix_UB_33      -0.0231518000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0639
_diffrn_reflns_av_unetI/netI     0.0474
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.943
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            60067
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.943
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.588
_diffrn_reflns_theta_min         3.338
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88694
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.79a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.309
_exptl_crystal_description       block
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.380
_refine_diff_density_min         -0.313
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     473
_refine_ls_number_reflns         10899
_refine_ls_number_restraints     25
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0723
_refine_ls_R_factor_gt           0.0514
_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^)+(0.0370P)^2^+1.1077P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1119
_refine_ls_wR_factor_ref         0.1232
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8296
_reflns_number_total             10899
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc01935k2.cif
_cod_data_source_block           s6380a
_cod_depositor_comments          'Adding full bibliography for 7133072.cif.'
_cod_database_code               7133072
_shelx_shelxl_version_number     2019/3
_shelx_estimated_absorpt_t_max   0.991
_shelx_estimated_absorpt_t_min   0.983
_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 C(H,H,H,H,H,H) groups
2. Restrained distances
 O3-C18 \\sim O3-C01F
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
C19 \\sim C18 \\sim C01F: within 2A with sigma of 0.006 and sigma for terminal
atoms of 0.012 within 2A
4. Rigid body (RIGU) restrains
 C01F, C18, C19
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Sof(H19D)=Sof(H19E)=Sof(H19F)=Sof(C01F)=Sof(H01A)=Sof(H01B)=1-FVAR(1)
 Sof(H19A)=Sof(H19B)=Sof(H19C)=Sof(C18)=Sof(H18A)=Sof(H18B)=FVAR(1)
6.a Secondary CH2 refined with riding coordinates:
 C28(H28A,H28B), C37(H37A,H37B), C9(H9A,H9B), C18(H18A,H18B), C01F(H01A,H01B)
6.b Aromatic/amide H refined with riding coordinates:
 C22(H22), C6(H6), C24(H24), C5(H5), C13(H13), C3(H3), C2(H2A), C15(H15),
 C31(H31), C21(H21), C12(H12), C25(H25), C11(H11), C16(H16), C35(H35), C34(H34),
  C33(H33), C32(H32)
6.c Idealised Me refined as rotating group:
 C38(H38A,H38B,H38C), C10(H10A,H10B,H10C), C29(H29A,H29B,H29C), C19(H19A,H19B,
 H19C), C19(H19D,H19E,H19F)
;
_shelx_res_checksum              33950
_shelx_hkl_checksum              93123
_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 1.228
_oxdiff_exptl_absorpt_empirical_full_min 0.714