Synthesis of maleimide-functionalized carboranes and their utility in Michael addition reactions
Ol'shevskaya, Valentina A.; Alpatova, Victoria M.; Makarenkov, Anton V.; Kononova, Elena G.; Smol’yakov, Alexander F.; Peregudov, Alexander S.; Rys, Evgeny G.; New Journal of Chemistry 45 (2021) 12159–12167; doi:10.1039/D1NJ02499J

data_7060767
_publ_section_title
;
 Synthesis of maleimide-functionalized carboranes and their utility in
 Michael addition reactions
;
_journal_issue                   27
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              12159
_journal_page_last               12167
_journal_paper_doi               10.1039/D1NJ02499J
_journal_volume                  45
_journal_year                    2021
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C8 H23 B20 N O2 S'
_chemical_formula_sum            'C8 H23 B20 N O2 S'
_chemical_formula_weight         413.828
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_symmetry_Int_Tables_number      1
_audit_creation_date             2021-06-09
_audit_creation_method
;
Olex2 1.5-dev
(compiled 2021.06.01 svn.r985b505f for OlexSys, GUI svn.r6225)
;
_audit_update_record
;
2021-06-10 deposited with the CCDC.	2021-06-18 downloaded from the CCDC.
;
_cell_angle_alpha                105.946(4)
_cell_angle_beta                 91.131(4)
_cell_angle_gamma                95.610(4)
_cell_formula_units_Z            1
_cell_length_a                   6.9661(17)
_cell_length_b                   7.0272(17)
_cell_length_c                   11.414(3)
_cell_measurement_reflns_used    1824
_cell_measurement_temperature    120
_cell_measurement_theta_max      29.43
_cell_measurement_theta_min      2.94
_cell_volume                     534.0(2)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 1.5-dev (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-dev (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5-dev (Bourhis et al., 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      120.00
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.9969
_diffrn_measured_fraction_theta_max 0.9972
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0250
_diffrn_reflns_av_unetI/netI     0.0795
_diffrn_reflns_Laue_measured_fraction_full 0.9969
_diffrn_reflns_Laue_measured_fraction_max 0.9972
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            6236
_diffrn_reflns_point_group_measured_fraction_full 0.9553
_diffrn_reflns_point_group_measured_fraction_max 0.9550
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         25.99
_diffrn_reflns_theta_min         1.86
_exptl_absorpt_coefficient_mu    0.160
_exptl_absorpt_correction_T_max  0.7459
_exptl_absorpt_correction_T_min  0.6145
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2008/1 (Bruker,2008) was used for absorption correction. wR2(int) was 0.0588 before and 0.0451 after correction. The Ratio of minimum to maximum transmission is 0.8238. The \l/2 correction factor is 0.0015.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.287
_exptl_crystal_description       plate
_exptl_crystal_F_000             210.168
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.3043
_refine_diff_density_min         -0.2585
_refine_diff_density_rms         0.0573
_refine_ls_abs_structure_details
'Hooft, R.W.W., Straver, L.H., Spek, A.L. (2010). J. Appl. Cryst., 43, 665-668.'
_refine_ls_abs_structure_Flack   -0.01(6)
_refine_ls_d_res_high            0.8109
_refine_ls_d_res_low             10.9614
_refine_ls_goodness_of_fit_ref   1.0748
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    45
_refine_ls_number_parameters     401
_refine_ls_number_reflns         4032
_refine_ls_number_restraints     316
_refine_ls_restrained_S_all      1.0313
_refine_ls_R_factor_all          0.0576
_refine_ls_R_factor_gt           0.0470
_refine_ls_shift/su_max          -0.0005
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0657P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1136
_refine_ls_wR_factor_ref         0.1200
_reflns_Friedel_coverage         0.913
_reflns_limit_h_max              8
_reflns_limit_h_min              -8
_reflns_limit_k_max              8
_reflns_limit_k_min              -8
_reflns_limit_l_max              14
_reflns_limit_l_min              -14
_reflns_number_gt                3552
_reflns_number_total             4032
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d1nj02499j2.cif
_cod_data_source_block           4
_cod_depositor_comments
'Adding full bibliography for 7060766--7060768.cif.'
_cod_original_sg_symbol_Hall     ' P 1'
_cod_database_code               7060767
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All B(H) groups, All C(H) groups
2. Shared sites
{C2A, B2A}
{C1A, B1A}
{B4A, C6}
{B8A, C8A}
3. Restrained distances
 S1R-C3 \\sim S1S-C3A
 with sigma of 0.02
 B9B-H10B \\sim B9C-H10C
 with sigma of 0.04
 S1R-B9B \\sim S1S-B9C
 with sigma of 0.02
 H4B-B8B \\sim H4C-B8C
 with sigma of 0.04
 O6-C2 \\sim O6A-C1
 with sigma of 0.02
 B7B-B10B \\sim C7C-B10C
 with sigma of 0.04
 O7-C5 \\sim O7A-C5A
 with sigma of 0.02
 C3B-H8B \\sim B3C-H8C
 with sigma of 0.04
 N1-C2 \\sim N1A-C1
 with sigma of 0.02
 C6B-H10B \\sim B6C-H10C
 with sigma of 0.04
 N1-C5 \\sim N1A-C5A
 with sigma of 0.02
 H11B-B12B \\sim H11C-B12C
 with sigma of 0.04
 N1-B3A \\sim N1A-B3A
 with sigma of 0.02
 H7B-B8B \\sim H7C-B8C
 with sigma of 0.04
 B1B-H1B \\sim C1C-H1C
 with sigma of 0.02
 H2B-C3B \\sim H2C-B3C
 with sigma of 0.04
 B4B-H5B \\sim B4C-H5C
 with sigma of 0.04
 B5B-B11B \\sim B5C-B11C
 with sigma of 0.04
 B8B-B10B \\sim B8C-B10C
 with sigma of 0.04
 B10B-H12B \\sim B10C-H12C
 with sigma of 0.04
 B7B-C6B \\sim C7C-B6C
 with sigma of 0.04
 C2-C3 \\sim C1-C3A
 with sigma of 0.02
 B7B-H12B \\sim C7C-H12C
 with sigma of 0.04
 C3-C4 \\sim C3A-C4A
 with sigma of 0.02
 C4-H4
 with sigma of 0.02
 C4-C5 \\sim C4A-C5A
 with sigma of 0.02
 C3B-H4B \\sim B3C-H4C
 with sigma of 0.04
 B7B-H7B \\sim C7C-H7C
 with sigma of 0.02
 B5B-B8B \\sim B5C-B8C
 with sigma of 0.04
 H5B-B9B \\sim H5C-B9C
 with sigma of 0.04
 B7B-H3B \\sim C7C-H3C
 with sigma of 0.04
 B2B-H2B \\sim B2C-H2C
 with sigma of 0.02
 B7B-H8B \\sim C7C-H8C
 with sigma of 0.04
 B2B-C3B \\sim B2C-B3C
 with sigma of 0.02
 B7B-H11B \\sim C7C-H11C
 with sigma of 0.04
 B2B-C6B \\sim B2C-B6C
 with sigma of 0.02
 H7B-B2B \\sim H7C-B2C
 with sigma of 0.04
 B2B-B11B \\sim B2C-B11C
 with sigma of 0.02
 H7B-B12B \\sim H7C-B12C
 with sigma of 0.04
 C3B-H3B \\sim B3C-H3C
 with sigma of 0.02
 B2B-B4B \\sim B2C-B4C
 with sigma of 0.04
 B2B-B8B \\sim B2C-B8C
 with sigma of 0.04
 B2B-B12B \\sim B2C-B12C
 with sigma of 0.04
 B4B-H4B \\sim B4C-H4C
 with sigma of 0.02
 H2B-B11B \\sim H2C-B11C
 with sigma of 0.04
 C3B-C6B \\sim B3C-B6C
 with sigma of 0.04
 C3B-B11B \\sim B3C-B11C
 with sigma of 0.04
 B4B-B9B \\sim B4C-B9C
 with sigma of 0.02
 H3B-B8B \\sim H3C-B8C
 with sigma of 0.04
 B5B-H5B \\sim B5C-H5C
 with sigma of 0.02
 B4B-B8B \\sim B4C-B8C
 with sigma of 0.04
 B4B-B12B \\sim B4C-B12C
 with sigma of 0.04
 B5B-C6B \\sim B5C-B6C
 with sigma of 0.04
 B5B-B10B \\sim B5C-B10C
 with sigma of 0.04
 C6B-H6B \\sim B6C-H6C
 with sigma of 0.02
 C6B-B9B \\sim B6C-B9C
 with sigma of 0.04
 C6B-H11B \\sim B6C-H11C
 with sigma of 0.04
 B8B-H8B \\sim B8C-H8C
 with sigma of 0.02
 H6B-B11B \\sim H6C-B11C
 with sigma of 0.04
 B8B-B12B \\sim B8C-B12C
 with sigma of 0.02
 H8B-B12B \\sim H8C-B12C
 with sigma of 0.04
 B9B-B12B \\sim B9C-B12C
 with sigma of 0.02
 B10B-H11B \\sim B10C-H11C
 with sigma of 0.04
 B10B-H10B \\sim B10C-H10C
 with sigma of 0.02
 H10B-B11B \\sim H10C-B11C
 with sigma of 0.04
 B11B-H12B \\sim B11C-H12C
 with sigma of 0.04
 B7B-B4B \\sim C7C-B4C
 with sigma of 0.04
 B11B-H11B \\sim B11C-H11C
 with sigma of 0.02
 B7B-B8B \\sim C7C-B8C
 with sigma of 0.04
 B7B-B9B \\sim C7C-B9C
 with sigma of 0.04
 B7B-B11B \\sim C7C-B11C
 with sigma of 0.04
 B12B-H12B \\sim B12C-H12C
 with sigma of 0.02
 B7B-B12B \\sim C7C-B12C
 with sigma of 0.04
 S1R-C2 \\sim S1S-C1
 with sigma of 0.04
 H7B-C3B \\sim H7C-B3C
 with sigma of 0.04
 S1R-C4 \\sim S1S-C4A
 with sigma of 0.04
 H7B-B11B \\sim H7C-B11C
 with sigma of 0.04
 S1R-B4B \\sim S1S-B4C
 with sigma of 0.04
 S1R-B5B \\sim S1S-B5C
 with sigma of 0.04
 B2B-H3B \\sim B2C-H3C
 with sigma of 0.04
 S1R-B8B \\sim S1S-B8C
 with sigma of 0.04
 B2B-B5B \\sim B2C-B5C
 with sigma of 0.04
 S1R-B10B \\sim S1S-B10C
 with sigma of 0.04
 B2B-H6B \\sim B2C-H6C
 with sigma of 0.04
 S1R-B12B \\sim S1S-B12C
 with sigma of 0.04
 B2B-B10B \\sim B2C-B10C
 with sigma of 0.04
 O6-N1 \\sim O6A-N1A
 with sigma of 0.04
 B2B-H11B \\sim B2C-H11C
 with sigma of 0.04
 O6-C3 \\sim O6A-C3A
 with sigma of 0.04
 O7-N1 \\sim O7A-N1A
 with sigma of 0.04
 H2B-C6B \\sim H2C-B6C
 with sigma of 0.04
 O7-C4 \\sim O7A-C4A
 with sigma of 0.04
 C3B-B4B \\sim B3C-B4C
 with sigma of 0.04
 N1-C3 \\sim N1A-C3A
 with sigma of 0.04
 C3B-B5B \\sim B3C-B5C
 with sigma of 0.04
 N1-C4 \\sim N1A-C4A
 with sigma of 0.04
 C3B-B8B \\sim B3C-B8C
 with sigma of 0.04
 B1B-B7B \\sim C1C-C7C
 with sigma of 0.04
 C3B-B9B \\sim B3C-B9C
 with sigma of 0.04
 B1B-B2B \\sim C1C-B2C
 with sigma of 0.04
 C3B-B12B \\sim B3C-B12C
 with sigma of 0.04
 B1B-H2B \\sim C1C-H2C
 with sigma of 0.04
 H3B-B4B \\sim H3C-B4C
 with sigma of 0.04
 B1B-C3B \\sim C1C-B3C
 with sigma of 0.04
 B4B-B5B \\sim B4C-B5C
 with sigma of 0.04
 B1B-H3B \\sim C1C-H3C
 with sigma of 0.04
 B4B-C6B \\sim B4C-B6C
 with sigma of 0.04
 B1B-B4B \\sim C1C-B4C
 with sigma of 0.04
 B4B-H8B \\sim B4C-H8C
 with sigma of 0.04
 B1B-H4B \\sim C1C-H4C
 with sigma of 0.04
 B4B-B10B \\sim B4C-B10C
 with sigma of 0.04
 B1B-B5B \\sim C1C-B5C
 with sigma of 0.04
 H4B-B5B \\sim H4C-B5C
 with sigma of 0.04
 B1B-H5B \\sim C1C-H5C
 with sigma of 0.04
 H4B-B9B \\sim H4C-B9C
 with sigma of 0.04
 B1B-C6B \\sim C1C-B6C
 with sigma of 0.04
 B5B-H6B \\sim B5C-H6C
 with sigma of 0.04
 B1B-H6B \\sim C1C-H6C
 with sigma of 0.04
 B5B-B9B \\sim B5C-B9C
 with sigma of 0.04
 B1B-B8B \\sim C1C-B8C
 with sigma of 0.04
 B5B-H10B \\sim B5C-H10C
 with sigma of 0.04
 B1B-B9B \\sim C1C-B9C
 with sigma of 0.04
 B5B-B12B \\sim B5C-B12C
 with sigma of 0.04
 B1B-B10B \\sim C1C-B10C
 with sigma of 0.04
 H5B-C6B \\sim H5C-B6C
 with sigma of 0.04
 B1B-B11B \\sim C1C-B11C
 with sigma of 0.04
 H5B-B10B \\sim H5C-B10C
 with sigma of 0.04
 H1B-B2B \\sim H1C-B2C
 with sigma of 0.04
 C6B-B10B \\sim B6C-B10C
 with sigma of 0.04
 H1B-C3B \\sim H1C-B3C
 with sigma of 0.04
 C6B-B11B \\sim B6C-B11C
 with sigma of 0.04
 H1B-B4B \\sim H1C-B4C
 with sigma of 0.04
 C6B-B12B \\sim B6C-B12C
 with sigma of 0.04
 H1B-B5B \\sim H1C-B5C
 with sigma of 0.04
 H6B-B10B \\sim H6C-B10C
 with sigma of 0.04
 H1B-C6B \\sim H1C-B6C
 with sigma of 0.04
 B8B-B9B \\sim B8C-B9C
 with sigma of 0.04
 C2-C4 \\sim C1-C4A
 with sigma of 0.04
 B8B-B11B \\sim B8C-B11C
 with sigma of 0.04
 C2-C5 \\sim C1-C5A
 with sigma of 0.04
 B8B-H12B \\sim B8C-H12C
 with sigma of 0.04
 C2-B3A \\sim C1-B3A
 with sigma of 0.04
 H8B-B9B \\sim H8C-B9C
 with sigma of 0.04
 C3-H4
 with sigma of 0.04
 B9B-B10B \\sim B9C-B10C
 with sigma of 0.04
 C3-C5 \\sim C3A-C5A
 with sigma of 0.04
 B9B-B11B \\sim B9C-B11C
 with sigma of 0.04
 C3-B9B \\sim C3A-B9C
 with sigma of 0.04
 B9B-H12B \\sim B9C-H12C
 with sigma of 0.04
 B10B-B11B \\sim B10C-B11C
 with sigma of 0.04
 B10B-B12B \\sim B10C-B12C
 with sigma of 0.04
 H4-C5
 with sigma of 0.04
 H10B-B12B \\sim H10C-B12C
 with sigma of 0.04
 C5-B3A \\sim C5A-B3A
 with sigma of 0.04
 B11B-B12B \\sim B11C-B12C
 with sigma of 0.04
 B7B-B2B \\sim C7C-B2C
 with sigma of 0.04
 B7B-H2B \\sim C7C-H2C
 with sigma of 0.04
 B7B-C3B \\sim C7C-B3C
 with sigma of 0.04
4. Uiso/Uaniso restraints and constraints
Uanis(C2A) = Uanis(B2A)
Uanis(C1A) = Uanis(B1A)
Uanis(B4A) = Uanis(C6)
Uanis(B8A) = Uanis(C8A)
5. Others
 Sof(S1S)=Sof(O6A)=Sof(O7A)=Sof(N1A)=Sof(C1C)=Sof(H1C)=Sof(C1)=Sof(C3A)=
 Sof(C4A)=Sof(H4Aa)=Sof(C5A)=Sof(C7C)=Sof(H7C)=Sof(B2C)=Sof(B3C)=Sof(H3C)=
 Sof(B4C)=Sof(H4C)=Sof(B5C)=Sof(H5C)=Sof(B6C)=Sof(H6C)=Sof(B8C)=Sof(H8C)=
 Sof(B9C)=Sof(B10C)=Sof(H10C)=Sof(B11C)=Sof(H11C)=Sof(B12C)=Sof(H12C)=Sof(H2C)=
 Sof(H4Aa)=Sof(H2A)=Sof(C2A)=Sof(C1A)=Sof(B4A)=Sof(B8A)=Sof(H8A)=Sof(H1A)=
 Sof(H2A)=Sof(H4A)=1-FVAR(1)
 Sof(S1R)=Sof(O6)=Sof(O7)=Sof(N1)=Sof(B1B)=Sof(H1B)=Sof(C2)=Sof(C3)=Sof(C4)=
 Sof(H4)=Sof(C5)=Sof(B7B)=Sof(H7B)=Sof(B2B)=Sof(H2B)=Sof(C3B)=Sof(H3B)=Sof(B4B)=
 Sof(H4B)=Sof(B5B)=Sof(H5B)=Sof(C6B)=Sof(H6B)=Sof(B8B)=Sof(H8B)=Sof(B9B)=
 Sof(B10B)=Sof(H10B)=Sof(B11B)=Sof(H11B)=Sof(B12B)=Sof(H12B)=Sof(B2A)=Sof(B1A)=
 Sof(C6)=Sof(C8A)=Sof(H6)=Sof(H8Aa)=Sof(H2Aa)=Sof(H1Aa)=FVAR(1)
 Fixed U11: S1S(0.030528)
 Fixed U12: S1S(-0.001165)
 Fixed U13: S1S(0.001882)
 Fixed U22: S1S(0.025951)
 Fixed U23: S1S(0.004324)
 Fixed U33: S1S(0.036061)
 Fixed Uiso: H1A(0.03) H1B(0.03) H2A(0.03) H4(0.03) H7B(0.03) H2B(0.03)
 H3B(0.03) H4A(0.03) H4B(0.03) H5A(0.03) H5B(0.03) H6A(0.03) H6B(0.03)
 H7A(0.03) H8A(0.03) H8B(0.03) H9A(0.03) H10A(0.03) H10B(0.03) H11A(0.03)
 H11B(0.03) H12A(0.03) H12B(0.03) B4C(0.03) B9C(0.03) O6A(0.03) B6C(0.03)
 O7A(0.03) H11C(0.03) N1A(0.03) B5C(0.03) C1C(0.03) B8C(0.03) H1C(0.03)
 H10C(0.03) C1(0.03) H12C(0.03) C3A(0.03) H4C(0.03) C4A(0.03) H5C(0.03)
 H4Aa(0.03) H6C(0.03) C5A(0.03) H8C(0.03) C7C(0.03) B10C(0.03) H7C(0.03)
 B11C(0.03) B2C(0.03) B12C(0.03) B3C(0.03) H2C(0.03) H3C(0.03)
6.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C4A(H4Aa)
6.b Boron cage BH refined with riding coordinates:
 B1B(H1B), B7B(H7B), B2B(H2B), C3B(H3B), B4B(H4B), B5A(H5A), B5B(H5B),
 B6A(H6A), C6B(H6B), B7A(H7A), B8A(H8A), B8B(H8B), B9A(H9A), B10A(H10A),
 B10B(H10B), B11A(H11A), B11B(H11B), B12A(H12A), B12B(H12B), C1A(H1A), C2A(H2A),
  C6(H6), C8A(H8Aa), B4A(H4A), B2A(H2Aa), B1A(H1Aa)
;
_olex2_submission_special_instructions 'No special instructions were received'