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_7063173
_publ_section_title
;
 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         'C3 H15 B12 O2, C16 H36 N'
_chemical_formula_sum            'C19 H51 B12 N O2'
_chemical_formula_weight         455.32
_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'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2024-02-01
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2024-03-19 deposited with the CCDC.	2024-04-03 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.05(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.167(6)
_cell_length_b                   21.48(3)
_cell_length_c                   14.716(16)
_cell_measurement_reflns_used    9679
_cell_measurement_temperature    100.00
_cell_measurement_theta_max      66.740
_cell_measurement_theta_min      3.655
_cell_volume                     2886(5)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_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      100.00
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0323
_diffrn_reflns_av_unetI/netI     0.0306
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            25006
_diffrn_reflns_point_group_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        66.675
_diffrn_reflns_theta_max         66.675
_diffrn_reflns_theta_min         3.650
_diffrn_source_current           1.1
_diffrn_source_power             0.05500000000000001
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.419
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.6375
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1081 before and 0.0667 after correction.
The Ratio of minimum to maximum transmission is 0.8468.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.048
_exptl_crystal_description       plate
_exptl_crystal_F_000             992
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.616
_refine_diff_density_min         -0.528
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.904
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     481
_refine_ls_number_reflns         5008
_refine_ls_number_restraints     8
_refine_ls_restrained_S_all      3.430
_refine_ls_R_factor_all          0.1103
_refine_ls_R_factor_gt           0.1063
_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^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3803
_refine_ls_wR_factor_ref         0.3888
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4572
_reflns_number_total             5008
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4nj01048e2.cif
_cod_data_source_block           2
_cod_depositor_comments
'Adding full bibliography for 7063172--7063175.cif.'
_cod_database_code               7063173
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.959
_shelx_estimated_absorpt_t_min   0.850
_olex2_refinement_description
;
1. Others
 Fixed Sof: O1A(0.5) O1B(0.5) O2A(0.5) O2B(0.5) C1A(0.5) C1B(0.5) C2A(0.5)
 H2AA(0.5) H2AB(0.5) C2B(0.5) H2BA(0.5) H2BB(0.5) C3A(0.5) H3AA(0.5) H3AB(0.5)
 H3AC(0.5) C3B(0.5) H3BA(0.5) H3BB(0.5) H3BC(0.5) H2(0.5) H4(0.5) C4A(0.5)
 H4AA(0.5) H4AB(0.5) C4B(0.5) H4BA(0.5) H4BB(0.5) C5A(0.5) H5AA(0.5) H5AB(0.5)
 C5B(0.5) H5BA(0.5) H5BB(0.5) C6A(0.5) H6AA(0.5) H6AB(0.5) C6B(0.5) H6BA(0.5)
 H6BB(0.5) C7A(0.5) H7AA(0.5) H7AB(0.5) H7AC(0.5) C7B(0.5) H7BA(0.5) H7BB(0.5)
 H7BC(0.5) C8A(0.5) H8AA(0.5) H8AB(0.5) C8B(0.5) H8BA(0.5) H8BB(0.5) C9A(0.5)
 H9AA(0.5) H9AB(0.5) C9B(0.5) H9BA(0.5) H9BB(0.5) C10A(0.5) H10A(0.5) H10B(0.5)
 C10B(0.5) H10C(0.5) H10D(0.5) C11A(0.5) H11A(0.5) H11B(0.5) H11C(0.5)
 C11B(0.5) H11D(0.5) H11E(0.5) H11F(0.5) C12A(0.5) H12A(0.5) H12B(0.5)
 C12B(0.5) H12C(0.5) H12D(0.5) C13A(0.5) H13A(0.5) H13B(0.5) C13B(0.5)
 H13C(0.5) H13D(0.5) C14A(0.5) H14A(0.5) H14B(0.5) C14B(0.5) H14C(0.5)
 H14D(0.5) C15A(0.5) H15A(0.5) H15B(0.5) H15C(0.5) C15B(0.5) H15D(0.5)
 H15E(0.5) H15F(0.5) C16A(0.5) H16A(0.5) H16B(0.5) C16B(0.5) H16C(0.5)
 H16D(0.5) C17A(0.5) H17A(0.5) H17B(0.5) C17B(0.5) H17C(0.5) H17D(0.5)
 H18A(0.5) H18B(0.5) H18C(0.5) H18D(0.5)
 Fixed Uiso: H2AA(0.204) H2AB(0.204) H2BA(0.155) H2BB(0.155) H3AA(0.254)
 H3AB(0.254) H3AC(0.254) H3BA(0.133) H3BB(0.133) H3BC(0.133) H2(0.076) H3(0.08)
 H4(0.071) H5(0.062) H6(0.064) H7(0.071) H8(0.063) H9(0.054) H10(0.057)
 H11(0.063) H12(0.057) H4AA(0.084) H4AB(0.084) H4BA(0.065) H4BB(0.065)
 H5AA(0.126) H5AB(0.126) H5BA(0.069) H5BB(0.069) H6AA(0.126) H6AB(0.126)
 H6BA(0.095) H6BB(0.095) H7AA(0.212) H7AB(0.212) H7AC(0.212) H7BA(0.234)
 H7BB(0.234) H7BC(0.234) H8AA(0.054) H8AB(0.054) H8BA(0.067) H8BB(0.067)
 H9AA(0.087) H9AB(0.087) H9BA(0.102) H9BB(0.102) H10A(0.068) H10B(0.068)
 H10C(0.091) H10D(0.091) H11A(0.173) H11B(0.173) H11C(0.173) H11D(0.185)
 H11E(0.185) H11F(0.185) H12A(0.065) H12B(0.065) H12C(0.062) H12D(0.062)
 H13A(0.09) H13B(0.09) H13C(0.08) H13D(0.08) H14A(0.08) H14B(0.08) H14C(0.12)
 H14D(0.12) H15A(0.114) H15B(0.114) H15C(0.114) H15D(0.178) H15E(0.178)
 H15F(0.178) H16A(0.069) H16B(0.069) H16C(0.063) H16D(0.063) H17A(0.074)
 H17B(0.074) H17C(0.07) H17D(0.07) H18A(0.091) H18B(0.091) H18C(0.091)
 H18D(0.091) H19A(0.135) H19B(0.135) H19C(0.135)
 Fixed X: H2AA(0.69632) H2AB(0.602605) H2BA(0.180652) H2BB(0.253224)
 H3AA(0.815743) H3AB(0.912944) H3AC(0.835505) H3BA(0.142292) H3BB(0.207267)
 H3BC(0.313631) H2(0.435998) H3(0.614763) H4(0.878726) H5(0.868011) H6(0.58927)
 H7(0.613763) H8(0.893712) H9(1.050569) H10(0.868942) H11(0.600184)
 H12(0.884014) H4AA(0.563725) H4AB(0.638845) H4BA(0.538314) H4BB(0.501884)
 H5AA(0.503859) H5AB(0.433959) H5BA(0.509927) H5BB(0.525215) H6AA(0.319287)
 H6AB(0.407503) H6BA(0.272926) H6BB(0.288655) H7AA(0.155757) H7AB(0.203061)
 H7AC(0.266683) H7BA(0.207446) H7BB(0.33857) H7BC(0.187153) H8AA(0.93613)
 H8AB(0.883304) H8BA(0.685364) H8BB(0.664636) H9AA(0.753777) H9AB(0.814207)
 H9BA(0.927328) H9BB(0.902183) H10A(0.995692) H10B(1.049408) H10C(0.804294)
 H10D(0.796859) H11A(1.030179) H11B(0.903564) H11C(0.865193) H11D(0.967652)
 H11E(1.072374) H11F(0.995949) H12A(0.851332) H12B(0.686879) H12C(0.757466)
 H12D(0.904714) H13A(0.916406) H13B(0.748226) H13C(0.858592) H13D(0.695296)
 H14A(0.884306) H14B(0.72538) H14C(0.847678) H14D(0.774052) H15A(0.837784)
 H15B(0.891397) H15C(0.995015) H15D(0.9784) H15E(1.008548) H15F(1.056573)
 H16A(0.638509) H16B(0.607699) H16C(0.886804) H16D(0.765989) H17A(0.874067)
 H17B(0.863703) H17C(0.730666) H17D(0.605809) H18A(0.692019) H18B(0.856626)
 H18C(0.877994) H18D(0.734904) H19A(0.639102) H19B(0.681988) H19C(0.799632)
 Fixed Y: H2AA(0.421262) H2AB(0.460783) H2BA(0.59164) H2BB(0.566861)
 H3AA(0.434134) H3AB(0.451719) H3AC(0.505479) H3BA(0.480078) H3BB(0.495917)
 H3BC(0.47177) H2(0.602593) H3(0.487878) H4(0.516665) H5(0.647948) H6(0.70067)
 H7(0.56779) H8(0.51301) H9(0.611706) H10(0.7261) H11(0.699662) H12(0.643431)
 H4AA(0.333651) H4AB(0.269707) H4BA(0.344356) H4BB(0.372251) H5AA(0.268337)
 H5AB(0.334938) H5BA(0.245278) H5BB(0.264233) H6AA(0.296143) H6AB(0.232317)
 H6BA(0.29931) H6BB(0.319779) H7AA(0.229728) H7AB(0.263852) H7AC(0.196321)
 H7BA(0.204781) H7BB(0.198888) H7BC(0.230413) H8AA(0.362942) H8AB(0.295017)
 H8BA(0.31258) H8BB(0.385855) H9AA(0.338386) H9AB(0.405662) H9BA(0.326121)
 H9BB(0.399492) H10A(0.305765) H10B(0.375395) H10C(0.324366) H10D(0.39788)
 H11A(0.363754) H11B(0.410443) H11C(0.339417) H11D(0.337867) H11E(0.352188)
 H11F(0.408257) H12A(0.345749) H12B(0.323412) H12C(0.250641) H12D(0.288602)
 H13A(0.250118) H13B(0.228114) H13C(0.295866) H13D(0.270611) H14A(0.26007)
 H14B(0.22926) H14C(0.196557) H14D(0.173516) H15A(0.137649) H15B(0.151691)
 H15C(0.168372) H15D(0.177261) H15E(0.143445) H15F(0.214425) H16A(0.428982)
 H16B(0.416712) H16C(0.401655) H16D(0.3919) H17A(0.435462) H17B(0.466831)
 H17C(0.470099) H17D(0.459074) H18A(0.536693) H18B(0.54428) H18C(0.516975)
 H18D(0.556004) H19A(0.483139) H19B(0.554752) H19C(0.50139)
 Fixed Z: H2AA(0.013674) H2AB(-0.06582) H2BA(0.075119) H2BB(-0.014518) H3AA(-
 0.129318) H3AB(-0.037211) H3AC(-0.09942) H3BA(0.042708) H3BB(0.144589)
 H3BC(0.071508) H2(0.217201) H3(0.222823) H4(0.128843) H5(0.068981)
 H6(0.122752) H7(0.386532) H8(0.330905) H9(0.237071) H10(0.233024)
 H11(0.323385) H12(0.394937) H4AA(0.380904) H4AB(0.414632) H4BA(0.561071)
 H4BB(0.461131) H5AA(0.54156) H5AB(0.513613) H5BA(0.511959) H5BB(0.407662)
 H6AA(0.383197) H6AB(0.394219) H6BA(0.507271) H6BB(0.40324) H7AA(0.421019)
 H7AB(0.515721) H7AC(0.495741) H7BA(0.465964) H7BB(0.401519) H7BC(0.363521)
 H8AA(0.459328) H8AB(0.428278) H8BA(0.35434) H8BB(0.36142) H9AA(0.296831)
 H9AB(0.327508) H9BA(0.368807) H9BB(0.370564) H10A(0.285974) H10B(0.309286)
 H10C(0.220973) H10D(0.223656) H11A(0.152265) H11B(0.177085) H11C(0.152377)
 H11D(0.136324) H11E(0.226727) H11F(0.168875) H12A(0.609556) H12B(0.619395)
 H12C(0.478402) H12D(0.503922) H13A(0.555567) H13B(0.539985) H13C(0.653002)
 H13D(0.631481) H14A(0.719702) H14B(0.70013) H14C(0.70259) H14D(0.606564)
 H15A(0.647228) H15B(0.751655) H15C(0.673083) H15D(0.545941) H15E(0.642672)
 H15F(0.631042) H16A(0.435924) H16B(0.539388) H16C(0.531861) H16D(0.602179)
 H17A(0.572814) H17B(0.47434) H17C(0.445564) H17D(0.512881) H18A(0.525761)
 H18B(0.569472) H18C(0.571788) H18D(0.536925) H19A(0.66004) H19B(0.676212)
 H19C(0.703414)
;
_shelx_res_checksum              92808
_shelx_hkl_checksum              63474
_olex2_submission_special_instructions 'No special instructions were received'