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

data_7135644
_publ_section_title
;
 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         'C15 H35 B21 Br N O3'
_chemical_formula_sum            'C15 H35 B21 Br N O3'
_chemical_formula_weight         584.36
_chemical_name_systematic        3
_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)
;
_audit_update_record
;
2026-01-16 deposited with the CCDC.	2026-03-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 118.883(5)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   21.6873(8)
_cell_length_b                   14.7154(3)
_cell_length_c                   21.3677(7)
_cell_measurement_reflns_used    18874
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      77.1610
_cell_measurement_theta_min      3.7910
_cell_volume                     5971.0(4)
_computing_cell_refinement       'CrysAlisPro 1.171.44.122a (Rigaku OD, 2025)'
_computing_data_collection       'CrysAlisPro 1.171.44.122a (Rigaku OD, 2025)'
_computing_data_reduction        'CrysAlisPro 1.171.44.122a (Rigaku OD, 2025)'
_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  (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 100'
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.938
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w   -124.00 -69.00   0.50    4.15    --  -47.68-132.00  81.00  110
  2  \w   -163.00 -82.00   0.50    4.15    --  -85.36-109.00 -21.00  162
  3  \w     34.00 107.00   0.50    4.15    --  111.19-109.00 -21.00  146
  4  \w     42.00 174.00   0.50    4.15    --  111.19  17.00 -63.00  264
  5  \w     42.00 174.00   0.50    4.15    --  111.19  17.00 -63.00  264
  6  \w     38.00 116.00   0.50    4.15    --  111.19-132.00  81.00  156
  7  \w    -38.00  34.00   0.50    4.15    --  -47.68  38.00  90.00  144
  8  \w     -9.00  35.00   0.50    4.15    --  -47.68  19.00   0.00   88
  9  \w     -5.00  35.00   0.50    4.15    --  -47.68  17.00 -63.00   80
 10  \w    -48.00  -4.00   0.50    4.15    --  -85.36  45.00-180.00   88
 11  \w    -76.00  -8.00   0.50    4.15    --  -85.36  61.00 150.00  136
 12  \w    -86.00 -13.00   0.50    4.15    --  -85.36 125.00   0.00  146
 13  \w    -91.00 -17.00   0.50    4.15    --  -85.36 132.00 151.00  148
 14  \w     34.00  76.00   0.50    4.15    --  111.19 -61.00-150.00   84
 15  \w     34.00  76.00   0.50    4.15    --  111.19 -61.00  30.00   84
 16  \w     34.00 112.00   0.50    4.15    --  111.19-125.00 120.00  156
 17  \w     38.00 105.00   0.50    4.15    --  111.19 -95.00 120.00  134
 18  \w     38.00 105.00   0.50    4.15    --  111.19 -95.00  60.00  134
 19  \w     34.00  76.00   0.50    4.15    --  111.19 -61.00 120.00   84
 20  \w     15.00  85.00   0.50    4.15    --   46.55  77.00-180.00  140
 21  \w   -118.00 -16.00   0.50    4.15    --  -47.68 -77.00  30.00  204
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix-Arc 100'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0148418000
_diffrn_orient_matrix_UB_12      0.0469524000
_diffrn_orient_matrix_UB_13      -0.0704040000
_diffrn_orient_matrix_UB_21      -0.0093734000
_diffrn_orient_matrix_UB_22      -0.0935055000
_diffrn_orient_matrix_UB_23      -0.0358795000
_diffrn_orient_matrix_UB_31      -0.0792520000
_diffrn_orient_matrix_UB_32      0.0021411000
_diffrn_orient_matrix_UB_33      -0.0233993000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0515
_diffrn_reflns_av_unetI/netI     0.0412
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.938
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            55191
_diffrn_reflns_point_group_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.938
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.127
_diffrn_reflns_theta_min         3.800
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.027
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86796
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.44.122a (Rigaku Oxford Diffraction, 2025)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_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    1.300
_exptl_crystal_description       block
_exptl_crystal_F_000             2368
_exptl_crystal_preparation       'GROWN FROM DCM INTO TOLUENE'
_exptl_crystal_size_max          0.185
_exptl_crystal_size_mid          0.092
_exptl_crystal_size_min          0.088
_refine_diff_density_max         1.335
_refine_diff_density_min         -0.660
_refine_diff_density_rms         0.109
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     755
_refine_ls_number_reflns         12135
_refine_ls_number_restraints     16
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.0890
_refine_ls_R_factor_gt           0.0781
_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^)+(0.0859P)^2^+30.5149P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2355
_refine_ls_wR_factor_ref         0.2420
_reflns_Friedel_coverage         0.000
_reflns_number_gt                10031
_reflns_number_total             12135
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d6cc01239f2.cif
_cod_data_source_block           3
_cod_depositor_comments
;
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.
;
_cod_database_code               7135644
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.842
_shelx_estimated_absorpt_t_min   0.706
_diffrn_oxdiff_digest_hkl
;
4365cc0a2e629cd926e1a057d2e1a2b815088a
;
_diffrn_oxdiff_measurement_exp_name CDM982R_KV_SR.par
_olex2_refinement_description
;
1. Uiso/Uaniso restraints and constraints
Br2 \\sim Br2A \\sim C17: within 2A with sigma of 0.04 and sigma for terminal
atoms of 0.08 within 2A
2. Rigid body (RIGU) restrains
 Br2, Br2A, C17
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
3. Others
 Sof(Br2A)=Sof(H17A)=1-FVAR(1)
 Sof(Br2)=Sof(H17)=FVAR(1)
4.a Ternary CH refined with riding coordinates:
 C2(H2), C17(H17), C17(H17A)
4.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C4(H4), C5(H5), C7(H7), C8(H8), C16(H16), C19(H19), C20(H20),
 C22(H22), C23(H23)
4.c Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C12(H12A,H12B,H12C), C15(H15A,H15B,H15C), C24(H24A,H24B,
 H24C), C27(H27A,H27B,H27C), C30(H30A,H30B,H30C)
4.d Boron cage BH refined with riding coordinates:
 B2(H2A), B3(H3), B4(H4A), B5(H5A), B6(H6), B7(H7A), B8(H8A), B9(H9), B10(H10),
  B11(H11), B12(H12), B13(H13), B14(H14), B15(H15), B16(H16A), B17(H17B),
 B18(H18), B19(H19A), B20(H20A), B21(H21), B23(H23A), B24(H24), B25(H25),
 B26(H26), B27(H27), B28(H28), B29(H29), B30(H30), B31(H31), B32(H32), B33(H33),
  B34(H34), B35(H35), B36(H36), B37(H37), B38(H38), B39(H39), B40(H40),
 B41(H41), B42(H42)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;