Facile amidinations of 2-aminophenylboronic acid promoted by boronate ester formation.
Pappin, Brighid B.; Garget, Taylor A.; Healy, Peter C.; Simone, Michela I.; Kiefel, Milton J.; Houston, Todd A.; Organic & biomolecular chemistry 17 (2019) 803–806; doi:10.1039/c8ob02696c

data_7156635
_publ_section_title
;
 Facile amidinations of 2-aminophenylboronic acid promoted by boronate
 ester formation.
;
_journal_issue                   4
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              803
_journal_page_last               806
_journal_paper_doi               10.1039/c8ob02696c
_journal_volume                  17
_journal_year                    2019
_chemical_formula_moiety         'C14 H13 B N2 O2, H2 O'
_chemical_formula_sum            'C14 H15 B N2 O3'
_chemical_formula_weight         270.09
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014
_audit_update_record
;
2018-06-11 deposited with the CCDC.
2019-01-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.821(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.0763(5)
_cell_length_b                   9.3343(7)
_cell_length_c                   20.5929(14)
_cell_measurement_reflns_used    2085
_cell_measurement_temperature    200(1)
_cell_measurement_theta_max      30.5260
_cell_measurement_theta_min      3.7850
_cell_volume                     1358.56(17)
_computing_cell_refinement       'CrysAlis PRO'
_computing_data_collection       'CrysAlis PRO (Agilent, 2013)'
_computing_data_reduction        'CrysAlis PRO'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SIR92 (Altomere, 1994)'
_diffrn_ambient_temperature      200(1)
_diffrn_detector_area_resol_mean 16.0774
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.878
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0247
_diffrn_reflns_av_unetI/netI     0.0372
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.878
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            8052
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.878
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.847
_diffrn_reflns_theta_min         3.416
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.97017
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.320
_exptl_crystal_description       block
_exptl_crystal_F_000             568
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: acetonitrile'
_exptl_crystal_size_max          0.470
_exptl_crystal_size_mid          0.370
_exptl_crystal_size_min          0.340
_refine_diff_density_max         0.389
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.653
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     198
_refine_ls_number_reflns         3760
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.653
_refine_ls_R_factor_all          0.0702
_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^)+(0.1707P)^2^+1.4463P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1541
_refine_ls_wR_factor_ref         0.1853
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2877
_reflns_number_total             3760
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8ob02696c2.cif
_cod_data_source_block           1118th21
_cod_depositor_comments
'Adding full bibliography for 7156633--7156636.cif.'
_cod_database_code               7156635
_shelx_estimated_absorpt_t_min   0.958
_shelx_estimated_absorpt_t_max   0.969
_shelxl_version_number           2014-3
_shelx_res_checksum              65274
_shelx_hkl_checksum              88899