1,4-Bromoboration of Nitroalkenes
Vashisth, Kanika; Martin, Caleb Daniel; Chemical Communications  (2026) –; doi:10.1039/D6CC01239F

data_7135643
_publ_section_title
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 1,4-Bromoboration of nitroalkenes.
;
_journal_issue                   27
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              7189
_journal_page_last               7193
_journal_paper_doi               10.1039/d6cc01239f
_journal_volume                  62
_journal_year                    2026
_chemical_formula_moiety         'C14 H33 B21 Br N O2'
_chemical_formula_sum            'C14 H33 B21 Br N O2'
_chemical_formula_weight         554.33
_chemical_name_systematic        1
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2026-01-07
_audit_creation_method
;
Olex2 1.5
(compiled 2025.07.13 svn.rb7424aed for OlexSys, GUI svn.r7308)
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_audit_update_record
;
2026-01-16 deposited with the CCDC.	2026-03-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.695(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.7150(3)
_cell_length_b                   19.7499(9)
_cell_length_c                   18.9664(9)
_cell_measurement_reflns_used    9888
_cell_measurement_temperature    150
_cell_measurement_theta_max      26.92
_cell_measurement_theta_min      2.33
_cell_volume                     2883.9(2)
_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 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      150
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0686
_diffrn_reflns_av_unetI/netI     0.0297
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            76288
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.101
_diffrn_reflns_theta_min         2.386
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.443
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6757
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0840 before and 0.0625 after correction.
The Ratio of minimum to maximum transmission is 0.9064.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.277
_exptl_crystal_description       block
_exptl_crystal_F_000             1120
_exptl_crystal_size_max          0.315
_exptl_crystal_size_mid          0.227
_exptl_crystal_size_min          0.102
_refine_diff_density_max         1.754
_refine_diff_density_min         -1.146
_refine_diff_density_rms         0.066
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     409
_refine_ls_number_reflns         6344
_refine_ls_number_restraints     264
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0621
_refine_ls_R_factor_gt           0.0513
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0398P)^2^+5.3170P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1209
_refine_ls_wR_factor_ref         0.1268
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5393
_reflns_number_total             6344
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d6cc01239f2.cif
_cod_data_source_block           1
_cod_depositor_comments
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The following automatic conversions were performed:

data item '_atom_sites_solution_primary' value 'DIRECT METHOD' was
changed to 'direct'.

Automatic conversion script
Id: cif_fix_values 8170 2020-07-09 18:12:32Z antanas 

 Adding full bibliography for 7135643--7135645.cif.
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_cod_database_code               7135643
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.867
_shelx_estimated_absorpt_t_min   0.659
_olex2_refinement_description
;
1. Uiso/Uaniso restraints and constraints
O1 \\sim O1A \\sim O2 \\sim O2A \\sim N1 \\sim N1A \\sim C1 \\sim C1A \\sim C2
\\sim C2A \\sim B1 \\sim B1A: within 2A with sigma of 0.04 and sigma for
terminal atoms of 0.08 within 2A
2. Rigid body (RIGU) restrains
 O1, O1A, O2, O2A, N1, N1A, C1, C1A, C2, C2A, B1, B1A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
3. Others
 Sof(O1A)=Sof(O2A)=Sof(N1A)=Sof(C1A)=Sof(H1A)=Sof(C2A)=Sof(H2A)=Sof(B1A)=1-
 FVAR(1)
 Sof(O1)=Sof(O2)=Sof(N1)=Sof(C1)=Sof(H1)=Sof(C2)=Sof(H2)=Sof(B1)=FVAR(1)
4.a Ternary CH refined with riding coordinates:
 C2(H2), C2A(H2A)
4.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C1A(H1A), C4(H4), C5(H5), C6(H6), C7(H7), C8(H8)
4.c Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C14(H14A,H14B,H14C)
4.d Boron cage BH refined with riding coordinates:
 B2(H2B), B3(H3), B4(H4A), B5(H5A), B6(H6A), B7(H7A), B8(H8A), B9(H9),
 B10(H10), B11(H11), B12(H12), B13(H13), B14(H14), B15(H15), B16(H16), B17(H17),
  B18(H18), B19(H19), B20(H20), B21(H21)
;
_olex2_submission_special_instructions 'No special instructions were received'