Carboxonium derivatives based on closo-dodecaborate anions [1,2-B12H10O2CR]−: synthesis and molecular orbital analysis
Kolbunova, Anastasia V.; Klyukin, Ilya N.; Novikov, Alexander S.; Nelyubin, Alexey V.; Zhdanov, Andrey P.; Kubasov, Alexey S.; Selivanov, Nikita A.; Bykov, Alexander Yu.; Zhizhin, Konstantin Yu.; Kuznetsov, Nikolay T.; New Journal of Chemistry 48 (2024) 8361–8370; doi:10.1039/D4NJ01048E

data_7063172
_publ_section_title
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 Carboxonium derivatives based on closo-dodecaborate anions
 [1,2-B12H10O2CR]&#x2212;: synthesis and molecular orbital analysis
;
_journal_issue                   18
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              8361
_journal_page_last               8370
_journal_paper_doi               10.1039/D4NJ01048E
_journal_volume                  48
_journal_year                    2024
_chemical_formula_moiety         'C2 H13 B12 O2, C16 H36 N'
_chemical_formula_sum            'C18 H49 B12 N O2'
_chemical_formula_weight         441.30
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2024-01-31
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2024-02-01 deposited with the CCDC.	2024-04-03 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   17.10(3)
_cell_length_b                   15.16(4)
_cell_length_c                   22.21(4)
_cell_measurement_reflns_used    4588
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      27.576
_cell_measurement_theta_min      2.211
_cell_volume                     5758(2)
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100.0
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0681
_diffrn_reflns_av_unetI/netI     0.0791
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            19274
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        24.998
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_min         2.016
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.056
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5806
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1374 before and 0.0627 after correction.
The Ratio of minimum to maximum transmission is 0.7787.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.018
_exptl_crystal_description       block
_exptl_crystal_F_000             1920
_exptl_crystal_size_max          0.8
_exptl_crystal_size_mid          0.8
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.302
_refine_diff_density_min         -0.206
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     310
_refine_ls_number_reflns         5050
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.015
_refine_ls_R_factor_all          0.1093
_refine_ls_R_factor_gt           0.0621
_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^)+(0.0677P)^2^+3.3336P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1461
_refine_ls_wR_factor_ref         0.1755
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3202
_reflns_number_total             5050
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4nj01048e2.cif
_cod_data_source_block           1
_cod_depositor_comments
'Adding full bibliography for 7063172--7063175.cif.'
_cod_original_cell_volume        5757(20)
_cod_database_code               7063172
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.989
_shelx_estimated_absorpt_t_min   0.957
_olex2_refinement_description
;
1. Others
 Fixed Sof: O1(0.9) O2(0.9) C1(0.9) C2(0.9) H2A(0.9) H2B(0.9) H2C(0.9) H1(0.1)
 H11(0.9) O4(0.1) O3(0.1) C19(0.1) C20(0.1) H20A(0.1) H20B(0.1) H20C(0.1)
 Fixed Uiso: H2A(0.063) H2B(0.063) H2C(0.063) H1(0.038) H3(0.036) H4(0.037)
 H5(0.04) H6(0.041) H7(0.037) H8(0.038) H9(0.037) H10(0.041) H11(0.039)
 H12(0.039) H3A(0.039) H3B(0.039) H4A(0.042) H4B(0.042) H5A(0.05) H5B(0.05)
 H6A(0.073) H6B(0.073) H6C(0.073) H7A(0.043) H7B(0.043) H8A(0.047) H8B(0.047)
 H9A(0.051) H9B(0.051) H10A(0.09) H10B(0.09) H10C(0.09) H11A(0.036) H11B(0.036)
 H12A(0.04) H12B(0.04) H13A(0.045) H13B(0.045) H14A(0.067) H14B(0.067)
 H14C(0.067) H15A(0.039) H15B(0.039) H16A(0.042) H16B(0.042) H17A(0.043)
 H17B(0.043) H18A(0.077) H18B(0.077) H18C(0.077) H20A(0.063) H20B(0.063)
 H20C(0.063)
 Fixed X: H2A(0.400987) H2B(0.37118) H2C(0.33783) H1(0.477532) H3(0.455042)
 H4(0.513147) H5(0.617126) H6(0.625795) H7(0.589264) H8(0.586654) H9(0.687612)
 H10(0.754676) H11(0.69394) H12(0.733795) H3A(0.477846) H3B(0.482512)
 H4A(0.347802) H4B(0.335186) H5A(0.401225) H5B(0.418159) H6A(0.312235)
 H6B(0.264734) H6C(0.283637) H7A(0.34209) H7B(0.399332) H8A(0.418531)
 H8B(0.465597) H9A(0.299161) H9B(0.343346) H10A(0.418782) H10B(0.327498)
 H10C(0.373765) H11A(0.366212) H11B(0.453345) H12A(0.367448) H12B(0.457356)
 H13A(0.334427) H13B(0.423808) H14A(0.351913) H14B(0.411035) H14C(0.320552)
 H15A(0.532788) H15B(0.551948) H16A(0.581535) H16B(0.593592) H17A(0.678185)
 H17B(0.688231) H18A(0.738746) H18B(0.792021) H18C(0.73167) H20A(0.657628)
 H20B(0.573959) H20C(0.650204)
 Fixed Y: H2A(0.577184) H2B(0.529211) H2C(0.624408) H1(0.748157) H3(0.707939)
 H4(0.883829) H5(0.860146) H6(0.668915) H7(0.594832) H8(0.788206) H9(0.882225)
 H10(0.749674) H11(0.570873) H12(0.703667) H3A(0.643384) H3B(0.543186)
 H4A(0.525655) H4B(0.629449) H5A(0.621926) H5B(0.51922) H6A(0.539784)
 H6B(0.590675) H6C(0.487827) H7A(0.584008) H7B(0.505245) H8A(0.605043)
 H8B(0.517051) H9A(0.523401) H9B(0.435376) H10A(0.437975) H10B(0.433823)
 H10C(0.525262) H11A(0.723455) H11B(0.760696) H12A(0.732344) H12B(0.762384)
 H13A(0.864464) H13B(0.895129) H14A(0.967526) H14B(0.900378) H14C(0.875196)
 H15A(0.64007) H15B(0.56219) H16A(0.745667) H16B(0.67166) H17A(0.677302)
 H17B(0.599574) H18A(0.704164) H18B(0.700205) H18C(0.779771) H20A(0.380222)
 H20B(0.383267) H20C(0.41604)
 Fixed Z: H2A(1.055122) H2B(0.995188) H2C(1.01283) H1(0.974154) H3(0.845185)
 H4(0.881599) H5(0.989041) H6(1.017946) H7(0.807775) H8(0.777936) H9(0.867004)
 H10(0.950227) H11(0.914524) H12(0.820518) H3A(0.554562) H3B(0.576267)
 H4A(0.567523) H4B(0.557702) H5A(0.463708) H5B(0.473773) H6A(0.406444)
 H6B(0.457897) H6C(0.465168) H7A(0.676856) H7B(0.659088) H8A(0.766755)
 H8B(0.749635) H9A(0.77296) H9B(0.751983) H10A(0.842016) H10B(0.85769)
 H10C(0.863032) H11A(0.625761) H11B(0.622462) H12A(0.731682) H12B(0.730933)
 H13A(0.676547) H13B(0.681235) H14A(0.75728) H14B(0.789213) H14C(0.782534)
 H15A(0.712439) H15B(0.666482) H16A(0.644714) H16B(0.593985) H17A(0.706287)
 H17B(0.658138) H18A(0.587235) H18B(0.646407) H18C(0.63722) H20A(0.941775)
 H20B(0.974002) H20C(1.009302)
;
_shelx_res_checksum              23786
_shelx_hkl_checksum              26139
_olex2_submission_special_instructions 'No special instructions were received'