Hetero Diels-Alder reactions of isolable <i>N</i>-borylenamines.
Liang, Pei; Wei, Junhui; Wei, Yongliang; Wang, Xue; Liu, Fei; Wang, Tongdao; Chemical communications (Cambridge, England) 60 (2024) 5964–5967; doi:10.1039/d4cc01645a

data_7133048
_publ_section_title
;
 Hetero Diels-Alder reactions of isolable <i>N</i>-borylenamines.
;
_journal_issue                   46
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              5964
_journal_page_last               5967
_journal_paper_doi               10.1039/d4cc01645a
_journal_volume                  60
_journal_year                    2024
_chemical_formula_moiety         'C29 H8 B F15 N2'
_chemical_formula_sum            'C29 H8 B F15 N2'
_chemical_formula_weight         680.18
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-I 2ya'
_space_group_name_H-M_alt        'I 1 2/a 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2024-03-13
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2024-04-08 deposited with the CCDC.	2024-05-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.003(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   13.6313(3)
_cell_length_b                   19.4305(6)
_cell_length_c                   24.1940(8)
_cell_measurement_reflns_used    12086
_cell_measurement_temperature    292.5(8)
_cell_measurement_theta_max      67.9900
_cell_measurement_theta_min      2.9110
_cell_volume                     6329.1(3)
_computing_cell_refinement       'CrysAlisPro 1.171.41.105a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.105a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.105a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.3 (Bourhis et al., 2015)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      292.5(8)
_diffrn_detector_type            'Bruker SMART CCD 6000 area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.992
_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     15.00  77.00   0.50   15.00    --   41.90  82.00  30.00  124
  2  \w    -40.00  56.00   0.50   15.00    --   41.90 -82.00   0.00  192
  3  \w     42.00  69.00   0.50   15.00    --   41.90 -82.00 -60.00   54
  4  \w     17.00  92.00   0.50   15.00    --   41.90  65.00 -60.00  150
  5  \w     46.00  79.00   0.50   15.00    --   41.90 -32.00  90.00   66
  6  \w    -47.00  62.00   0.50   15.00    --   41.90 -65.00 120.00  218
  7  \w    -30.00  -5.00   0.50   15.00    --   41.90 -82.00 150.00   50
  8  \w    -33.00  -7.00   0.50   15.00    --   41.90 -82.00 -60.00   52
  9  \w     41.00  66.00   0.50   15.00    --   41.90 -65.00  60.00   50
 10  \w    -41.00 -12.00   0.50   15.00    --   41.90 -82.00-120.00   58
 11  \w     86.00 129.00   0.50   15.00    --   41.90  32.00   0.00   86
 12  \w    -40.00   2.00   0.50   15.00    --   41.90 -65.00  60.00   84
 13  \w      4.00  31.00   0.50   15.00    --   41.90 -32.00  90.00   54
 14  \w    -39.00  72.00   0.50   15.00    --   41.90 -54.00-120.00  222
 15  \w     50.00  77.00   0.50   15.00    --   41.90  32.00   0.00   54
 16  \w     37.00  69.00   0.50   15.00    --   41.90 -82.00 150.00   64
 17  \w    -22.00  20.00   0.50   15.00    --   41.90 -82.00  90.00   84
 18  \w    -20.00  44.00   0.50   15.00    --   41.90 -65.00-180.00  128
 19  \w     26.00  69.00   0.50   15.00    --   41.90 -82.00  90.00   86
 20  \w    -44.00  -5.00   0.50   15.00    --   41.90 -77.00 -60.00   78
 21  \w     10.00  35.00   0.50   15.00    --   41.90 -77.00 -60.00   50
 22  \w    -15.00  10.00   0.50   15.00    --   41.90 -82.00-180.00   50
 23  \w     44.00  69.00   0.50   15.00    --   41.90 -82.00-180.00   50
 24  \w      0.00  69.00   0.50   15.00    --   41.90 -82.00-120.00  138
 25  \w    -46.00  67.00   0.50   15.00    --   41.90 -82.00  60.00  226
 26  \w    -47.00 -22.00   0.50   15.00    --   41.90 -32.00  90.00   50
 27  \w     31.00  66.00   0.50   22.00    --   94.40 -82.00-120.00   70
 28  \w     17.00  93.00   0.50   22.00    --   94.40 -82.00 -90.00  152
 29  \w      5.00 129.00   0.50   22.00    --   94.40 -33.00 120.00  248
 30  \w      6.00 184.00   0.50   22.00    --   94.40  17.00 120.00  356
 31  \w     36.00  92.00   0.50   22.00    --   94.40 -82.00  90.00  112
 32  \w    158.00 184.00   0.50   22.00    --   94.40  -8.00  90.00   52
 33  \w     31.00 101.00   0.50   22.00    --   94.40 -82.00-150.00  140
 34  \w     12.00  78.00   0.50   22.00    --   94.40 -33.00 -90.00  132
 35  \w     11.00 126.00   0.50   22.00    --   94.40 -42.00 -30.00  230
 36  \w     17.00 111.00   0.50   22.00    --   94.40 -82.00 120.00  188
 37  \w     67.00  97.00   0.50   22.00    --   94.40 -82.00   0.00   60
 38  \w     49.00  95.00   0.50   22.00    --   94.40 -82.00  30.00   92
 39  \w     50.00  95.00   0.50   22.00    --   94.40 -82.00  60.00   90
 40  \w     62.00 102.00   0.50   22.00    --   94.40 -82.00-180.00   80
 41  \w      5.00 112.00   0.50   22.00    --   94.40 -59.00 -90.00  214
 42  \w     69.00 100.00   0.50   22.00    --   94.40 -82.00 -60.00   62
 43  \w      5.00  30.00   0.50   22.00    --   94.40 -82.00 -60.00   50
 44  \w     86.00 112.00   0.50   22.00    --   94.40 -82.00-120.00   52
 45  \w     72.00 107.00   0.50   22.00    --   94.40 -50.00  90.00   70
 46  \w     66.00  96.00   0.50   22.00    --   94.40 -82.00 -30.00   60
 47  \w     42.00 151.00   0.50   22.00    --   94.40  -8.00  90.00  218
 48  \w      5.00  92.00   0.50   22.00    --   94.40 -82.00 145.49  174
;
_diffrn_measurement_device_type  'Bruker SMART CCD 6000'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0288057000
_diffrn_orient_matrix_UB_12      -0.0343864000
_diffrn_orient_matrix_UB_13      0.0525420000
_diffrn_orient_matrix_UB_21      -0.1094882000
_diffrn_orient_matrix_UB_22      -0.0016718000
_diffrn_orient_matrix_UB_23      -0.0280702000
_diffrn_orient_matrix_UB_31      0.0164991000
_diffrn_orient_matrix_UB_32      -0.0714043000
_diffrn_orient_matrix_UB_33      -0.0246951000
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0470
_diffrn_reflns_av_unetI/netI     0.0264
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            31061
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.242
_diffrn_reflns_theta_min         2.931
_diffrn_source_target            Mo
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.323
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.47492
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.105a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.428
_exptl_crystal_description       block
_exptl_crystal_F_000             2688
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.676
_refine_diff_density_min         -0.368
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.103
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     424
_refine_ls_number_reflns         5772
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.103
_refine_ls_R_factor_all          0.0885
_refine_ls_R_factor_gt           0.0714
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1375P)^2^+4.7941P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2313
_refine_ls_wR_factor_ref         0.2472
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4186
_reflns_number_total             5772
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc01645a2.cif
_cod_data_source_block           20230110a_auto_sq
_cod_depositor_comments
'Adding full bibliography for 7133047--7133054.cif.'
_cod_database_code               7133048
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C H O N F'
_chemical_oxdiff_usercomment     LP-388
_shelx_estimated_absorpt_t_max   0.902
_shelx_estimated_absorpt_t_min   0.857
_reflns_odcompleteness_completeness 99.98
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B)
2.b Aromatic/amide H refined with riding coordinates:
 N2(H2), C11(H11), C6(H6), C3(H3), C5(H5), C4(H4)
;
_shelx_res_checksum              38578
_shelx_hkl_checksum              69191
_shelx_fab_checksum              87299
_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
;
_oxdiff_exptl_absorpt_empirical_full_max 3.809
_oxdiff_exptl_absorpt_empirical_full_min 0.208