Palladium-catalysed Suzuki-Miyaura coupling of α,β-unsaturated superactive triazine esters.
Lin, Dezhi; Yang, Hongyu; Zhang, Xiao; Sun, Huaming; Zhang, Xuepeng; Jian, Yajun; Zhang, Weiqiang; Liu, Yunfang; Gao, Ziwei; Chemical communications (Cambridge, England) 59 (2023) 4810–4813; doi:10.1039/d3cc00336a

data_7131476
_publ_section_title
;
 Palladium-catalysed Suzuki-Miyaura coupling of
 &#x3b1;,&#x3b2;-unsaturated superactive triazine esters.
;
_journal_issue                   32
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              4810
_journal_page_last               4813
_journal_paper_doi               10.1039/d3cc00336a
_journal_volume                  59
_journal_year                    2023
_chemical_formula_moiety         'C14 H13 N3 O4'
_chemical_formula_sum            'C14 H13 N3 O4'
_chemical_formula_weight         287.27
_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     dual
_audit_creation_date             2021-10-14
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2023-01-13 deposited with the CCDC.	2023-03-24 downloaded from the CCDC.
;
_cell_angle_alpha                93.171(3)
_cell_angle_beta                 96.973(3)
_cell_angle_gamma                104.307(4)
_cell_formula_units_Z            4
_cell_length_a                   8.3286(3)
_cell_length_b                   11.3682(5)
_cell_length_c                   15.5301(5)
_cell_measurement_reflns_used    9657
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      71.5720
_cell_measurement_theta_min      4.7250
_cell_volume                     1408.69(10)
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0356
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.989
_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     18.00  91.00   1.00    1.00    --   37.78-125.00  30.00   73
  2  \w     26.00  98.00   1.00    1.00    --   37.78-137.00 -34.00   72
  3  \w     21.00 105.00   1.00    1.00    --   37.78  57.00 120.00   84
  4  \w     19.00 107.00   1.00    1.00    --   37.78  37.00 -90.00   88
  5  \w    -31.00  57.00   1.00    1.00    --   37.78 -37.00 -90.00   88
  6  \w    -30.00  65.00   1.00    1.00    --   37.78 -77.00  30.00   95
  7  \w     11.00 105.00   1.00    1.00    --   37.78  77.00 150.00   94
  8  \w     18.00  91.00   1.00    1.00    --   37.78-125.00   0.00   73
  9  \w     39.00 125.00   1.00    3.31    --  107.59 -45.00 150.00   86
 10  \w     38.00 112.00   1.00    3.31    --  107.59-111.00 -90.00   74
 11  \w     41.00 126.00   1.00    3.31    --  107.59 -61.00 -30.00   85
 12  \w     38.00 112.00   1.00    3.31    --  107.59-111.00 120.00   74
 13  \w     38.00 110.00   1.00    3.31    --  107.59 -94.00 -30.00   72
 14  \w     39.00 125.00   1.00    3.31    --  107.59 -45.00  60.00   86
 15  \w     90.00 174.00   1.00    3.31    --  107.59  61.00 120.00   84
 16  \w     39.00 125.00   1.00    3.31    --  107.59 -45.00 -90.00   86
 17  \w    100.00 178.00   1.00    3.31    --  107.59 111.00  60.00   78
 18  \w     39.00 125.00   1.00    3.31    --  107.59 -45.00 -30.00   86
 19  \w     40.00 134.00   1.00    3.31    --  107.59 -77.00 120.00   94
 20  \w     38.00 177.00   1.00    3.31    --  107.59   0.00  90.00  139
 21  \w     11.00 105.00   1.00    1.00    --   37.78  77.00  30.00   94
 22  \w    -31.00  57.00   1.00    1.00    --   37.78 -37.00-180.00   88
 23  \w     21.00 105.00   1.00    1.00    --   37.78  57.00   0.00   84
 24  \w     -4.00  77.00   1.00    1.00    --   37.78 -99.00 150.00   81
 25  \w     11.00 105.00   1.00    1.00    --   37.78  77.00-150.00   94
 26  \w     11.00 105.00   1.00    1.00    --   37.78  77.00 -60.00   94
 27  \w     21.00 105.00   1.00    1.00    --   37.78  57.00 -60.00   84
 28  \w    -31.00  57.00   1.00    1.00    --   37.78 -37.00  90.00   88
 29  \w     81.00 175.00   1.00    3.31    --  107.59  77.00  60.00   94
 30  \w     81.00 175.00   1.00    3.31    --  107.59  77.00   0.00   94
 31  \w     81.00 175.00   1.00    3.31    --  107.59  77.00 -60.00   94
 32  \w     86.00 178.00   1.00    3.31    --  107.59  30.00-180.00   92
 33  \w     86.00 178.00   1.00    3.31    --  107.59  30.00-150.00   92
 34  \w     81.00 175.00   1.00    3.31    --  107.59  77.00-150.00   94
 35  \w     69.00 178.00   1.00    3.31    --  107.59  15.00 -60.00  109
 36  \w     81.00 175.00   1.00    3.31    --  107.59  77.00  90.00   94
 37  \w     11.00 105.00   1.00    1.00    --   37.78  77.00  90.00   94
 38  \w     19.00 107.00   1.00    1.00    --   37.78  37.00-180.00   88
 39  \w     19.00 107.00   1.00    1.00    --   37.78  37.00  60.00   88
 40  \w     11.00 105.00   1.00    1.00    --   37.78  77.00 -30.00   94
 41  \w     11.00 105.00   1.00    1.00    --   37.78  77.00 -90.00   94
 42  \w     11.00 105.00   1.00    1.00    --   37.78  77.00 120.00   94
 43  \w    -31.00 107.00   1.00    1.00    --   37.78   0.00  30.00  138
 44  \w     19.00 107.00   1.00    1.00    --   37.78  37.00 -60.00   88
 45  \w     81.00 154.00   1.00    3.31    --  107.59  77.00 -30.00   73
;
_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      -0.0314572000
_diffrn_orient_matrix_UB_12      -0.0050628000
_diffrn_orient_matrix_UB_13      -0.1001204000
_diffrn_orient_matrix_UB_21      -0.0037859000
_diffrn_orient_matrix_UB_22      0.1349843000
_diffrn_orient_matrix_UB_23      0.0061373000
_diffrn_orient_matrix_UB_31      0.1901594000
_diffrn_orient_matrix_UB_32      0.0383068000
_diffrn_orient_matrix_UB_33      -0.0022391000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0338
_diffrn_reflns_av_unetI/netI     0.0211
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            25876
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.578
_diffrn_reflns_theta_min         4.029
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.627
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.63615
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.218
_exptl_crystal_F_000             546
_refine_diff_density_max         0.180
_refine_diff_density_min         -0.308
_refine_diff_density_rms         0.073
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     378
_refine_ls_number_reflns         5429
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0542
_refine_ls_R_factor_gt           0.0469
_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^)+(0.0684P)^2^+0.2748P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1210
_refine_ls_wR_factor_ref         0.1287
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4595
_reflns_number_total             5429
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc00336a2.cif
_cod_data_source_block           exp_17806
_cod_depositor_comments
;
          Adding full bibliography for 7131476.cif.

2025-01-31
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C11 H10 N O'
_cod_original_formula_weight         172.20
_cod_original_formula_moiety         '0.667(C14 H13 N3 O4)'
_cod_original_formula_units_Z            6
_cod_database_code               7131476
_shelx_shelxl_version_number     2018/3
_reflns_odcompleteness_completeness 99.98
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C00G(H00G), C00R(H00R), C00S(H00S), C00T(H00T), C00U(H00U), C00V(H00V),
 C00W(H00W), C00X(H00X), C00Y(H00Y), C00Z(H00Z), C010(H010), C011(H011),
 C014(H014), C1(H1)
2.b Idealised Me refined as rotating group:
 C012(H01G,H01H,H01I), C013(H01A,H01B,H01C), C015(H01D,H01E,H01F), C016(H01J,
 H01K,H01L)
;