Empowering boronic acids as hydroxyl synthons for aryne induced three-component coupling reactions.
Fan, Rong; Liu, Shihan; Yan, Qiang; Wei, Yun; Wang, Jingwen; Lan, Yu; Tan, Jiajing; Chemical science 14 (2023) 4278–4287; doi:10.1039/d3sc00072a

data_1568661
_publ_section_title
;
 Empowering boronic acids as hydroxyl synthons for aryne induced
 three-component coupling reactions.
;
_journal_issue                   16
_journal_name_full               'Chemical science'
_journal_page_first              4278
_journal_page_last               4287
_journal_paper_doi               10.1039/d3sc00072a
_journal_volume                  14
_journal_year                    2023
_chemical_formula_moiety         'C18 H15 N O'
_chemical_formula_sum            'C18 H15 N O'
_chemical_formula_weight         261.31
_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
_atom_sites_solution_secondary   difmap
_audit_creation_date             2020-10-14
_audit_creation_method
;
  Olex2 1.1
  (compiled 2011.02.15 svn.r1672, GUI svn.r3494)
;
_audit_update_record
;
2021-06-02 deposited with the CCDC.	2023-03-13 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 97.987(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   14.8247(4)
_cell_length_b                   11.5912(3)
_cell_length_c                   15.5420(4)
_cell_measurement_reflns_used    3857
_cell_measurement_temperature    112.15(10)
_cell_measurement_theta_max      29.3230
_cell_measurement_theta_min      3.9630
_cell_volume                     2644.77(12)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution
'A short history of SHELX (Sheldrick, 2007)/Bruker'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      112.15(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0971
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9970
_diffrn_measured_fraction_theta_max 0.8395
_diffrn_measurement_details
;
  1 omega  -32.00   39.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -13.2647   37.0000  120.0000 71

  2 omega   17.00   47.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       18.5772    0.0000  -60.0000 30

  3 omega    9.00   36.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -13.2647   57.0000 -180.0000 27

  4 omega  -48.00  -15.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       18.5772    0.0000  -60.0000 33

  5 omega  -23.00   26.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -13.2647  -99.0000   60.0000 49

  6 omega  -20.00   58.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       18.5772  -99.0000  -60.0000 78
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0292326000
_diffrn_orient_matrix_UB_12      -0.0455920000
_diffrn_orient_matrix_UB_13      -0.0167032000
_diffrn_orient_matrix_UB_21      -0.0293734000
_diffrn_orient_matrix_UB_22      0.0403434000
_diffrn_orient_matrix_UB_23      -0.0240758000
_diffrn_orient_matrix_UB_31      0.0248616000
_diffrn_orient_matrix_UB_32      -0.0059703000
_diffrn_orient_matrix_UB_33      -0.0355816000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0335
_diffrn_reflns_av_unetI/netI     0.0431
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            14473
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         3.18
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90182
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.313
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1104
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.37
_exptl_crystal_size_min          0.35
_refine_diff_density_max         0.233
_refine_diff_density_min         -0.248
_refine_diff_density_rms         0.046
_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     363
_refine_ls_number_reflns         5185
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0643
_refine_ls_R_factor_gt           0.0446
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0443P)^2^+0.4818P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0980
_refine_ls_wR_factor_ref         0.1104
_reflns_number_gt                3861
_reflns_number_total             5185
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d3sc00072a2.cif
_cod_data_source_block           exp_6516
_cod_depositor_comments
'Adding full bibliography for 1568660--1568661.cif.'
_cod_original_cell_volume        2644.75(11)
_cod_database_code               1568661
_reflns_odcompleteness_completeness 99.70
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32