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_7061844
_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_absolute_configuration unk
_chemical_formula_moiety         'C8 H17 B10 I N2'
_chemical_formula_sum            'C8 H17 B10 I N2'
_chemical_formula_weight         376.385
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_Int_Tables_number      19
_audit_creation_date             2022-08-20
_audit_creation_method
;
Olex2 1.5-dev
(compiled 2022.07.25 svn.r36e0af09 for OlexSys, GUI svn.r6444)
;
_audit_update_record
;
2022-08-24 deposited with the CCDC.	2022-08-30 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.2029(3)
_cell_length_b                   12.1616(5)
_cell_length_c                   18.3542(7)
_cell_measurement_reflns_used    9203
_cell_measurement_temperature    120
_cell_measurement_theta_max      29.44
_cell_measurement_theta_min      2.22
_cell_volume                     1607.81(11)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_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 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      120.00
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.9994
_diffrn_measured_fraction_theta_max 0.9995
_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  0.0496
_diffrn_reflns_av_unetI/netI     0.0420
_diffrn_reflns_Laue_measured_fraction_full 0.9994
_diffrn_reflns_Laue_measured_fraction_max 0.9995
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            32931
_diffrn_reflns_point_group_measured_fraction_full 0.9993
_diffrn_reflns_point_group_measured_fraction_max 0.9994
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         25.99
_diffrn_reflns_theta_min         2.01
_exptl_absorpt_coefficient_mu    1.975
_exptl_absorpt_correction_T_max  0.3803
_exptl_absorpt_correction_T_min  0.2881
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0837 before and 0.0536 after correction.
The Ratio of minimum to maximum transmission is 0.7576.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.555
_exptl_crystal_description       prism
_exptl_crystal_F_000             726.698
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.2595
_refine_diff_density_min         -0.2415
_refine_diff_density_rms         0.0545
_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   -0.023(12)
_refine_ls_d_res_high            0.8108
_refine_ls_d_res_low             10.1380
_refine_ls_extinction_coef       0.0014
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_goodness_of_fit_ref   1.0278
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     344
_refine_ls_number_reflns         3158
_refine_ls_number_restraints     522
_refine_ls_restrained_S_all      0.9440
_refine_ls_R_factor_all          0.0185
_refine_ls_R_factor_gt           0.0154
_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^)+(0.0020P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0244
_refine_ls_wR_factor_ref         0.0246
_reflns_Friedel_coverage         0.999
_reflns_limit_h_max              8
_reflns_limit_h_min              -8
_reflns_limit_k_max              14
_reflns_limit_k_min              -14
_reflns_limit_l_max              22
_reflns_limit_l_min              -22
_reflns_number_gt                2933
_reflns_number_total             3158
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d2nj03509j2.cif
_cod_data_source_block           13
_cod_depositor_comments
'Adding full bibliography for 7061844--7061846.cif.'
_cod_original_sg_symbol_Hall     ' P 2ac 2ab'
_cod_database_code               7061844
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All B(H) groups, All C(H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(H12) \\sim Ueq: with sigma of 0.001 and sigma for terminal atoms of 0.002
3. Rigid body (RIGU) restrains
 B11, I1, B9, B5, B10, B12, B8, B4, C1, B6, H5, H10, B7, H12, B3, H8, H4, C2,
 C3, H6, H11, H7, H3, C6, H3a, H3b, C4, H6a, H6b, C7, H4a, H4b, C5, H7a, H7b,
 C8, N1, N2
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
;
_olex2_refine_details
;
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:      x2c-TZVP
   CHARGE:         0
   MULTIPLICITY:   1
   RELATIVISTIC:   DKH2
   DATE:           2022-08-19_18-49-07
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_olex2_submission_special_instructions 'No special instructions were received'