Boronic Acid Mediated Coupling of Catechols and N-Hydroxylamines: A Bioorthogonal Reaction to Label Peptides.
Meadows, Margaret K.; Roesner, Emily K.; Lynch, Vincent M.; James, Tony D.; Anslyn, Eric V.; Organic letters 19 (2017) 3179–3182; doi:10.1021/acs.orglett.7b01198

data_1546469
_publ_section_title
;
 Boronic Acid Mediated Coupling of Catechols and N-Hydroxylamines: A
 Bioorthogonal Reaction to Label Peptides.
;
_journal_issue                   12
_journal_name_full               'Organic letters'
_journal_page_first              3179
_journal_page_last               3182
_journal_paper_doi               10.1021/acs.orglett.7b01198
_journal_volume                  19
_journal_year                    2017
_chemical_formula_moiety         'C17 H18 B N O3'
_chemical_formula_sum            'C17 H18 B N O3'
_chemical_formula_weight         295.13
_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'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 104.357(4)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   22.032(4)
_cell_length_b                   6.0534(10)
_cell_length_c                   22.854(4)
_cell_measurement_reflns_used    1785
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      1.47
_cell_volume                     2952.8(9)
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_molecular_graphics    'XP SHELXTL/PC, Siemens Analytical'
_computing_publication_material  'XP SHELXTL/PC, Siemens Analytical'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution
;

SIR97 - Altomare A., Burla M.C., Camalli M., Cascarano G.L., Giacovazzo C., 
Guagliardi A., Moliterni A.G.G., Polidori G.,Spagna R.
;
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Rigaku SCX-Mini with Mercury 2+ CCD'
_diffrn_measurement_method       \w-scans
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0628
_diffrn_reflns_av_unetI/netI     0.0514
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            27432
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.503
_diffrn_reflns_theta_min         3.136
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_correction_T_min  0.821
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
Abscor. T. Higashi (2001). The Rigaku Corporation, Tokyo, Japan.
;
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.328
_exptl_crystal_description       needle
_exptl_crystal_F_000             1248
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.230
_exptl_crystal_size_min          0.150
_refine_diff_density_max         0.320
_refine_diff_density_min         -0.260
_refine_diff_density_rms         0.057
_refine_ls_extinction_coef       0.0049(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     412
_refine_ls_number_reflns         6734
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0627
_refine_ls_R_factor_gt           0.0486
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0502P)^2^+1.0916P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1127
_refine_ls_wR_factor_ref         0.1195
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5507
_reflns_number_total             6734
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol7b01198_si_002.cif
_cod_data_source_block           shelx
_cod_original_cell_volume        2952.8(8)
_cod_database_code               1546469
_shelx_estimated_absorpt_t_min   0.972
_shelx_estimated_absorpt_t_max   0.987
_shelxl_version_number           2013-4
_shelx_res_checksum              5670
_shelx_hkl_checksum              63157