Scalable, Metal- and Additive-Free, Photoinduced Borylation of Haloarenes and Quaternary Arylammonium Salts.
Mfuh, Adelphe M.; Doyle, John D.; Chhetri, Bhuwan; Arman, Hadi D.; Larionov, Oleg V.; Journal of the American Chemical Society 138 (2016) 2985–2988; doi:10.1021/jacs.6b01376

data_4130231
_publ_section_title
;
 Scalable, Metal- and Additive-Free, Photoinduced Borylation of Haloarenes
 and Quaternary Arylammonium Salts.
;
_journal_issue                   9
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              2985
_journal_page_last               2988
_journal_paper_doi               10.1021/jacs.6b01376
_journal_volume                  138
_journal_year                    2016
_chemical_formula_moiety         'C7 H6 B N O2, 2(H2 O)'
_chemical_formula_sum            'C7 H10 B N O4'
_chemical_formula_weight         182.97
_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   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2015-11-09
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_cell_angle_alpha                93.315(7)
_cell_angle_beta                 91.465(6)
_cell_angle_gamma                94.628(7)
_cell_formula_units_Z            2
_cell_length_a                   3.7693(4)
_cell_length_b                   8.5103(11)
_cell_length_c                   14.0577(17)
_cell_measurement_reflns_used    2179
_cell_measurement_temperature    98
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.7
_cell_volume                     448.51(9)
_computing_cell_refinement
;
CrystalClear-SM Auto 2.0 r15 (Rigaku, 2011)
;
_computing_data_collection
;
CrystalClear-SM Auto 2.0 r15 (Rigaku, 2011)
;
_computing_data_reduction
;
CrystalClear-SM Auto 2.0 r15 (Rigaku, 2011)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      98
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_details
;
scan:
	Number of images: 246
	           Slice: -68.0000 - 55.0000
	     Image width: 0.5000
	        Exp time: 45.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 70.0000
	             Phi: 90.0000
	             XTD: 35.0000
	          2theta: -35.0000
scan:
	Number of images: 126
	           Slice: -61.0000 - 2.0000
	     Image width: 0.5000
	        Exp time: 45.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 70.0000
	             Phi: 270.0000
	             XTD: 35.0000
	          2theta: -35.0000
scan:
	Number of images: 120
	           Slice: -80.0000 - -20.0000
	     Image width: 0.5000
	        Exp time: 45.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 0.0000
	             Phi: 270.0000
	             XTD: 35.0000
	          2theta: -35.0000
scan:
	Number of images: 80
	           Slice: -67.0000 - -27.0000
	     Image width: 0.5000
	        Exp time: 45.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 70.0000
	             Phi: 0.0000
	             XTD: 35.0000
	          2theta: -35.0000
scan:
	Number of images: 60
	           Slice: -115.0000 - -85.0000
	     Image width: 0.5000
	        Exp time: 45.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 0.0000
	             Phi: 180.0000
	             XTD: 35.0000
	          2theta: -35.0000
;
_diffrn_measurement_device
;
AFC12 (Right): Kappa 3 circle
;
_diffrn_measurement_device_type
;
Rigaku Saturn724 (2x2 bin mode)
;
_diffrn_measurement_method       'profile data from \w-scans'
_diffrn_measurement_specimen_support Fiber
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      0.261753
_diffrn_orient_matrix_UB_12      0.011899
_diffrn_orient_matrix_UB_13      0.022866
_diffrn_orient_matrix_UB_21      0.008391
_diffrn_orient_matrix_UB_22      0.110285
_diffrn_orient_matrix_UB_23      -0.040007
_diffrn_orient_matrix_UB_31      -0.004513
_diffrn_orient_matrix_UB_32      0.028322
_diffrn_orient_matrix_UB_33      0.064912
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0256
_diffrn_reflns_av_unetI/netI     0.0447
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       3
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            2549
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        25.041
_diffrn_reflns_theta_max         25.041
_diffrn_reflns_theta_min         3.659
_diffrn_source                   'Sealed Tube'
_diffrn_source_current           40.0
_diffrn_source_power             2.0
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.108
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.439
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Higashi, 1995)'
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.355
_exptl_crystal_description       needle
_exptl_crystal_F_000             192
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.490
_refine_diff_density_min         -0.381
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     136
_refine_ls_number_reflns         1573
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.008
_refine_ls_R_factor_all          0.0861
_refine_ls_R_factor_gt           0.0663
_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^)+(0.0200P)^2^+0.8500P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1328
_refine_ls_wR_factor_ref         0.1436
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1198
_reflns_number_total             1573
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja6b01376_si_002.cif
_cod_data_source_block           cd1377a
_cod_database_code               4130231
_shelx_estimated_absorpt_t_max   0.989
_shelx_estimated_absorpt_t_min   0.948
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups, All O(H,H) groups, All O(H,H,H,H,H) groups
2. Restrained distances
 H3B-O3
 0.8 with sigma of 0.02
 H3B-O4A
 1.8 with sigma of 0.02
3. Others
 Fixed Sof: O4B(0.5) H4BA(0.5) H4BB(0.5) O4A(0.5) H4AA(0.5) H4AB(0.5)
4.a Free rotating group:
 O3(H3A), O4B(H4BA,H4BB), O4A(H1,H2,H3B,H4AA,H4AB)
4.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C3(H3), C2(H2A), C6(H6)
;
_shelx_shelxl_version_number     2014/7
_olex2_exptl_crystal_mounting_method 'glass fiber'
_olex2_submission_special_instructions 'No special instructions were received'