Synthesis of substituted benzooxaborinin-1-ols via palladium-catalysed cyclisation of alkenyl- and alkynyl-boronic acids.
Benhamou, Laure; Walker, Daniel W.; Bučar, Dejan-Krešimir; Aliev, Abil E.; Sheppard, Tom D.; Organic & biomolecular chemistry 14 (2016) 8039–8043; doi:10.1039/c6ob01419d

data_7155222
_publ_section_title
;
 Synthesis of substituted benzooxaborinin-1-ols via palladium-catalysed
 cyclisation of alkenyl- and alkynyl-boronic acids.
;
_journal_issue                   34
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              8039
_journal_page_last               8043
_journal_paper_doi               10.1039/c6ob01419d
_journal_volume                  14
_journal_year                    2016
_chemical_formula_moiety         'C14 H10 B1 Cl1 O2'
_chemical_formula_sum            'C14 H10 B Cl O2'
_chemical_formula_weight         256.48
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2016-05-10T17:16:17-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_update_record
;
2016-05-10 deposited with the CCDC.
2016-08-01 downloaded from the CCDC.
;
_cell_angle_alpha                84.309(2)
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_cell_length_b                   11.2966(3)
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_cell_measurement_reflns_used    11908
_cell_measurement_temperature    150.0(7)
_cell_measurement_theta_max      73.4690
_cell_measurement_theta_min      4.0750
_cell_volume                     1219.62(5)
_computing_cell_refinement
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
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_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.0(7)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2031
_diffrn_detector_type            Atlas
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_diffrn_measurement_device       'four-circle diffractometer'
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_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0221
_diffrn_reflns_av_unetI/netI     0.0173
_diffrn_reflns_Laue_measured_fraction_full 0.997
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_diffrn_reflns_point_group_measured_fraction_full 0.997
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_diffrn_reflns_theta_full        66.6
_diffrn_reflns_theta_max         66.6
_diffrn_reflns_theta_min         4.096
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.674
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91406
_exptl_absorpt_correction_type   multi-scan
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;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.397
_exptl_crystal_description       prism
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.234
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.035
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
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_refine_ls_number_reflns         4305
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0309
_refine_ls_R_factor_gt           0.029
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0419P)^2^+0.3709P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0776
_refine_ls_wR_factor_ref         0.0793
_reflns_Friedel_coverage         0
_reflns_number_gt                4018
_reflns_number_total             4305
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6ob01419d2.cif
_cod_data_source_block           3e
_cod_depositor_comments          'Adding full bibliography for 7155222.cif.'
_cod_original_formula_sum        'C14 H10 B1 Cl1 O2'
_cod_database_code               7155222