Employment of Michael addition reactions for the functionalization of carboranes
Rys, Evgeny G.; Alpatova, Victoria M.; Kononova, Elena G.; Smol’yakov, Alexander F.; Moiseev, Sergey K.; Ol'shevskaya, Valentina A.; New Journal of Chemistry 46 (2022) 18025–18032; doi:10.1039/D2NJ03509J

data_7061846
_publ_section_title
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 Employment of Michael addition reactions for the functionalization of
 carboranes
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_journal_issue                   37
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              18025
_journal_page_last               18032
_journal_paper_doi               10.1039/D2NJ03509J
_journal_volume                  46
_journal_year                    2022
_chemical_formula_moiety         'C8 H19 B10 N O3, C2 H4 O2'
_chemical_formula_sum            'C10 H23 B10 N O5'
_chemical_formula_weight         345.540
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_Int_Tables_number      2
_audit_creation_date             2022-08-24
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
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2022-08-24 deposited with the CCDC.	2022-08-30 downloaded from the CCDC.
;
_cell_angle_alpha                62.736(1)
_cell_angle_beta                 85.701(1)
_cell_angle_gamma                86.130(1)
_cell_formula_units_Z            2
_cell_length_a                   7.4064(1)
_cell_length_b                   11.1792(2)
_cell_length_c                   12.0917(2)
_cell_measurement_reflns_used    9902
_cell_measurement_temperature    100
_cell_measurement_theta_max      29.64
_cell_measurement_theta_min      3.27
_cell_volume                     886.82(3)
_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  'olex2.refine 1.5-dev (Bourhis et al., 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.9994
_diffrn_measured_fraction_theta_max 0.9994
_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  0.0236
_diffrn_reflns_av_unetI/netI     0.0197
_diffrn_reflns_Laue_measured_fraction_full 0.9994
_diffrn_reflns_Laue_measured_fraction_max 0.9994
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            22816
_diffrn_reflns_point_group_measured_fraction_full 0.9994
_diffrn_reflns_point_group_measured_fraction_max 0.9994
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.05
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  0.7459
_exptl_absorpt_correction_T_min  0.6455
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1112 before and 0.0381 after correction.
The Ratio of minimum to maximum transmission is 0.8654.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.294
_exptl_crystal_description       prism
_exptl_crystal_F_000             360.225
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.2180
_refine_diff_density_min         -0.0922
_refine_diff_density_rms         0.0265
_refine_ls_d_res_high            0.8108
_refine_ls_d_res_low             9.9303
_refine_ls_goodness_of_fit_ref   1.1211
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    1
_refine_ls_number_parameters     470
_refine_ls_number_reflns         3475
_refine_ls_number_restraints     111
_refine_ls_restrained_S_all      1.1010
_refine_ls_R_factor_all          0.0214
_refine_ls_R_factor_gt           0.0205
_refine_ls_shift/su_max          -0.0002
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0150P)^2^+0.1369P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0491
_refine_ls_wR_factor_ref         0.0496
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              9
_reflns_limit_h_min              -9
_reflns_limit_k_max              13
_reflns_limit_k_min              -12
_reflns_limit_l_max              14
_reflns_limit_l_min              0
_reflns_number_gt                3340
_reflns_number_total             3475
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d2nj03509j2.cif
_cod_data_source_block           22
_cod_depositor_comments
'Adding full bibliography for 7061844--7061846.cif.'
_cod_database_code               7061846
_olex2_refinement_description
;
1. Restrained distances
 C2S-H2Sa \\sim C2S-H2Sd
 with sigma of 0.02
 C2S-H2Sb \\sim C2S-H2Se
 with sigma of 0.02
 C2S-H2Sc \\sim C2S-H2Sf
 with sigma of 0.02
2. Rigid body (RIGU) restrains
 C1S, O1S, O2S, C2S, H2S, H2Sa, H2Sb, H2Sc, H2Sd, H2Se, H2Sf
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
3. Others
 Sof(H2Sd)=Sof(H2Se)=Sof(H2Sf)=1-FVAR(1)
 Sof(H2Sa)=Sof(H2Sb)=Sof(H2Sc)=FVAR(1)
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_olex2_refine_details
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Refinement using NoSpherA2, an implementation of
NOn-SPHERical Atom-form-factors in Olex2.
Please cite:
F. Kleemiss et al. Chem. Sci. DOI 10.1039/D0SC05526C - 2021
NoSpherA2 implementation of HAR makes use of
tailor-made aspherical atomic form factors calculated
on-the-fly from a Hirshfeld-partitioned electron density (ED) - not from
spherical-atom form factors.

The ED is calculated from a gaussian basis set single determinant SCF
wavefunction - either Hartree-Fock or DFT using selected funtionals
 - for a fragment of the crystal.
This fragment can be embedded in an electrostatic crystal field by employing cluster charges
or modelled using implicit solvation models, depending on the software used.
The following options were used:
   SOFTWARE:       ORCA 5.0
   PARTITIONING:   NoSpherA2
   INT ACCURACY:   Normal
   METHOD:         R2SCAN
   BASIS SET:      cc-pVTZ
   CHARGE:         0
   MULTIPLICITY:   1
   DATE:           2022-08-20_12-54-31
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_olex2_submission_special_instructions 'No special instructions were received'