Ureas are identified as the first neutral O-donors broadly effective in stabilizing ionic liquids and other salts of boron-centred cations: synthesis and detailed characterization
Crowley, Margaret E.; Merchant, Gabriel A.; Davis, James H.; Stachurski, Christopher D.; Zeller, Matthias; Salter, E. A.; Wierzbicki, A.; Trulove, Paul C.; Durkin, David P.; Kingrey, Grace L.; Escalante, Edgar E.; O'Brien, Richard A.; Whillock, Novita M.; RSC Advances 15 (2025) 40519–40527; doi:10.1039/D5RA05311K

data_7251132
_publ_section_title
;
 Ureas are identified as the first neutral O-donors broadly effective in
 stabilizing ionic liquids and other salts of boron-centred cations:
 synthesis and detailed characterization
;
_journal_issue                   48
_journal_name_full               'RSC Advances'
_journal_page_first              40519
_journal_page_last               40527
_journal_paper_doi               10.1039/D5RA05311K
_journal_volume                  15
_journal_year                    2025
_chemical_formula_moiety         'C8 H21 B N3 O, I'
_chemical_formula_sum            'C8 H21 B I N3 O'
_chemical_formula_weight         312.99
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2019/3
_audit_update_record
;
2025-07-15 deposited with the CCDC.	2025-10-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 107.192(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.6367(6)
_cell_length_b                   12.7626(7)
_cell_length_c                   11.3363(6)
_cell_measurement_reflns_used    9971
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      33.1567
_cell_measurement_theta_min      2.2123
_cell_volume                     1331.95(13)
_computing_cell_refinement       'SAINT V8.40B (Bruker, 2020)'
_computing_data_collection       'Apex4 v2022.10-1 (Bruker, 2022)'
_computing_data_reduction        'SAINT V8.40B (Bruker, 2020)'
_computing_structure_refinement
;  
SHELXL-2019/2 (Sheldrick, 2015a, 2019), 
SHELXLE Rev1573 (H\"ubschle et al., 2011)
;
_computing_structure_solution    'SHELXT (Sheldrick, 2015b)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 7.4074
_diffrn_detector_type
'PhotonII charge-integrating pixel array (CPAD)'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_device       'three circle diffractometer'
_diffrn_measurement_device_type  'Bruker AXS D8 Quest'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_radiation_monochromator  'Triumph curved graphite crystal'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0787
_diffrn_reflns_av_unetI/netI     0.0606
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            25245
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         33.162
_diffrn_reflns_theta_min         2.467
_diffrn_source                   'fine focus sealed tube X-ray source'
_diffrn_source_current           '30 mA'
_diffrn_source_voltage           '50 kV'
_exptl_absorpt_coefficient_mu    2.382
_exptl_absorpt_correction_T_max  0.7465
_exptl_absorpt_correction_T_min  0.5017
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.561
_exptl_crystal_description       plate
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.550
_exptl_crystal_size_mid          0.520
_exptl_crystal_size_min          0.040
_refine_diff_density_max         0.937
_refine_diff_density_min         -1.370
_refine_diff_density_rms         0.131
_refine_ls_extinction_coef       0.0025(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     134
_refine_ls_number_reflns         4954
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.018
_refine_ls_R_factor_all          0.0626
_refine_ls_R_factor_gt           0.0362
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0396P)^2^+0.6720P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0863
_refine_ls_wR_factor_ref         0.0962
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3637
_reflns_number_total             4954
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ra05311k2.cif
_cod_data_source_block           11-I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7251132
_shelx_shelxl_version_number     2019/3
_shelx_estimated_absorpt_t_min   0.354
_shelx_estimated_absorpt_t_max   0.911
_shelx_res_checksum              74440