BNN-1,3-dipoles: isolation and intramolecular cycloaddition with unactivated arenes
Guo, Rui; Jiang, Jingxing; Hu, Chenyang; Liu, Liu Leo; Cui, Ping; Zhao, Meihua; Ke, Zhuofeng; Tung, Chen-Ho; Kong, Lingbing; Chemical Science  (2020) –; doi:10.1039/D0SC02162H

data_1558371
_publ_section_title
;
 BNN-1,3-dipoles: isolation and intramolecular cycloaddition with
 unactivated arenes
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D0SC02162H
_journal_year                    2020
_chemical_formula_moiety         'C36 H60 B2 Br2 N2'
_chemical_formula_sum            'C36 H60 B2 Br2 N2'
_chemical_formula_weight         702.30
_space_group_crystal_system      trigonal
_space_group_IT_number           148
_space_group_name_Hall           '-R 3'
_space_group_name_H-M_alt        'R -3 :H'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-05-20
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-05-25 deposited with the CCDC.	2020-06-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            9
_cell_length_a                   32.9585(3)
_cell_length_b                   32.9585(3)
_cell_length_c                   9.9663(2)
_cell_measurement_reflns_used    11419
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      70.9440
_cell_measurement_theta_min      4.6160
_cell_volume                     9375.6(2)
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      173.0
_diffrn_detector_area_resol_mean 8.1281
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_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     -8.00  21.00   1.00    5.00    --    0.00  57.00  73.00   29
  2  \w    -25.00  16.00   1.00    5.00    --    0.00  77.00 -30.00   41
  3  \w     21.00  69.00   1.00    5.00    --    0.00  77.00 -30.00   48
  4  \w     31.00  65.00   1.00    5.00    --    0.00  57.00  73.00   34
  5  \w    -64.00  -6.00   1.00    5.00    --    0.00 -57.00-120.00   58
  6  \w     32.00 124.00   1.00   20.00    --   54.47  77.00  90.00   92
  7  \w      5.00  74.00   1.00   20.00    --   54.47 -57.00 120.00   69
  8  \w     38.00 110.00   1.00   20.00    --   54.47-125.00  60.00   72
  9  \w     30.00 123.00   1.00   20.00    --   54.47  37.00  30.00   93
 10  \w     20.00  55.00   1.00   20.00    --   54.47 -57.00-180.00   35
 11  \w     68.00  99.00   1.00   20.00    --   54.47 -19.00 120.00   31
 12  \w     -2.00  24.00   1.00   20.00    --   54.47 -19.00 120.00   26
 13  \w     -2.00  67.00   1.00   20.00    --   54.47 -57.00-120.00   69
 14  \w    142.00 176.00   1.00   20.00    --  108.95  50.00   0.00   34
 15  \w     87.00 112.00   1.00   20.00    --  108.95  50.00   0.00   25
 16  \w     39.00  77.00   1.00   20.00    --  108.95-111.00-150.00   38
 17  \w     38.00 112.00   1.00   20.00    --  108.95-111.00  30.00   74
 18  \w     40.00 142.00   1.00   20.00    --  108.95 -25.00-180.00  102
 19  \w    104.00 154.00   1.00   20.00    --  108.95 111.00-120.00   50
 20  \w    119.00 145.00   1.00   20.00    --  108.95 178.00  60.00   26
 21  \w     46.00 131.00   1.00   20.00    --  108.95 -50.00 -30.00   85
 22  \w     63.00 137.00   1.00   20.00    --  108.95 -77.00  30.00   74
 23  \w     60.00  99.00   1.00   20.00    --  108.95 178.00  60.00   39
 24  \w     37.00 113.00   1.00   20.00    --  108.95-111.00-120.00   76
 25  \w     80.00 110.00   1.00   20.00    --  108.95-111.00 150.00   30
 26  \w     42.00 124.00   1.00   20.00    --  108.95 -25.00  60.00   82
 27  \w     40.00 152.00   1.00   20.00    --  108.95  12.00  90.00  112
 28  \w     42.00 131.00   1.00   20.00    --  108.95 -63.00-150.00   89
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0194
_diffrn_reflns_av_unetI/netI     0.0114
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       39
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -39
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            20723
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        66.569
_diffrn_reflns_theta_max         66.569
_diffrn_reflns_theta_min         2.681
_exptl_absorpt_coefficient_mu    2.621
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84856
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.119
_exptl_crystal_description       plate
_exptl_crystal_F_000             3330
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.651
_refine_diff_density_min         -0.460
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         3651
_refine_ls_number_restraints     139
_refine_ls_restrained_S_all      1.090
_refine_ls_R_factor_all          0.0604
_refine_ls_R_factor_gt           0.0559
_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^)+(0.1017P)^2^+18.1644P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1635
_refine_ls_wR_factor_ref         0.1691
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3255
_reflns_number_total             3651
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0sc02162h2.cif
_cod_data_source_block           klb-5_sq
_cod_original_cell_volume        9375.6(3)
_cod_original_sg_symbol_H-M      'R -3'
_cod_database_code               1558371
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.780
_shelx_estimated_absorpt_t_min   0.420
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C16B-C15 = C17A-C15 = C17B-C15 = C18A-C15 = C18B-C15 = C16A-C15 = C12A-C11 =
 C12B-C11 = C13A-C11 = C14B-C11 = C14A-C11 = C13B-C11
 1.53 with sigma of 0.02
 Br1A-B1 \\sim Br1B-B1
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
C12A \\sim C12B \\sim C13A \\sim C13B \\sim C14A \\sim C14B: within 2A with
sigma of 0.001 and sigma for terminal atoms of 0.002
Br1A \\sim Br1B: within 2A with sigma of 0.001 and sigma for terminal atoms of
0.002
Uanis(C12B) \\sim Ueq, Uanis(C13A) \\sim Ueq, Uanis(C13B) \\sim Ueq,
Uanis(C14A) \\sim Ueq, Uanis(C14B) \\sim Ueq, Uanis(C12A) \\sim Ueq: with sigma
of 0.01 and sigma for terminal atoms of 0.02
Uanis(C18B) \\sim Ueq, Uanis(C16A) \\sim Ueq, Uanis(C16B) \\sim Ueq,
Uanis(C17A) \\sim Ueq, Uanis(C17B) \\sim Ueq, Uanis(C18A) \\sim Ueq: with sigma
of 0.01 and sigma for terminal atoms of 0.02
Uanis(Br1B) \\sim Ueq, Uanis(Br1A) \\sim Ueq: with sigma of 0.001 and sigma for
terminal atoms of 0.02
4. Others
 Sof(Br1B)=1-FVAR(1)
 Sof(Br1A)=FVAR(1)
 Sof(C12B)=Sof(H12d)=Sof(H12e)=Sof(H12f)=Sof(C13B)=Sof(H13d)=Sof(H13e)=
 Sof(H13f)=Sof(C14B)=Sof(H14d)=Sof(H14e)=Sof(H14f)=1-FVAR(2)
 Sof(C12A)=Sof(H12a)=Sof(H12b)=Sof(H12c)=Sof(C13A)=Sof(H13a)=Sof(H13b)=
 Sof(H13c)=Sof(C14A)=Sof(H14a)=Sof(H14b)=Sof(H14c)=FVAR(2)
 Sof(C16B)=Sof(H16d)=Sof(H16e)=Sof(H16f)=Sof(C17B)=Sof(H17d)=Sof(H17e)=
 Sof(H17f)=Sof(C18B)=Sof(H18d)=Sof(H18e)=Sof(H18f)=1-FVAR(3)
 Sof(C16A)=Sof(H16a)=Sof(H16b)=Sof(H16c)=Sof(C17A)=Sof(H17a)=Sof(H17b)=
 Sof(H17c)=Sof(C18A)=Sof(H18a)=Sof(H18b)=Sof(H18c)=FVAR(3)
5.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C3(H3), C5(H5)
5.b Idealised Me refined as rotating group:
 C8(H8a,H8b,H8c), C9(H9a,H9b,H9c), C10(H10a,H10b,H10c), C12A(H12a,H12b,H12c),
 C12B(H12d,H12e,H12f), C13A(H13a,H13b,H13c), C13B(H13d,H13e,H13f), C14A(H14a,
 H14b,H14c), C14B(H14d,H14e,H14f), C16A(H16a,H16b,H16c), C16B(H16d,H16e,H16f),
 C17A(H17a,H17b,H17c), C17B(H17d,H17e,H17f), C18A(H18a,H18b,H18c), C18B(H18d,
 H18e,H18f)
;
_shelx_res_checksum              51331
_shelx_fab_checksum              59042
_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
;