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_1558372
_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         'C24 H26 B Br N'
_chemical_formula_sum            'C24 H26 B Br N'
_chemical_formula_weight         419.18
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2020-05-19
_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                 118.076(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.4204(6)
_cell_length_b                   13.4075(4)
_cell_length_c                   13.5682(5)
_cell_measurement_reflns_used    5356
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      76.1910
_cell_measurement_theta_min      3.7450
_cell_volume                     2154.09(17)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      173.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_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    -88.00 -62.00   1.00    0.10    --  -48.45-155.00 175.00   26
  2  \w   -119.00 -74.00   1.00    0.10    --  -48.45-120.00 -28.00   45
  3  \w    -87.00 -35.00   1.00    0.10    --  -48.45 120.00  56.00   52
  4  \w     28.00  93.00   1.00    0.10    --   48.45-120.00 -28.00   65
  5  \w     57.00  82.00   1.00    0.10    --   48.45-155.00 175.00   25
  6  \w   -141.00-116.00   1.00    0.43    --  -86.25-120.00 -28.00   25
  7  \w     82.00 137.00   1.00    0.43    --  107.75-155.00 175.00   55
  8  \w     97.00 153.00   1.00    0.43    --  107.75 120.00  56.00   56
  9  \w     69.00 113.00   1.00    0.43    --  107.75-120.00 -28.00   44
 10  \w   -120.00 -26.00   1.00    0.10    --  -48.45 -77.00 -30.00   94
 11  \w     35.00 122.00   1.00    0.43    --  107.75 -57.00 -60.00   87
 12  \w     35.00 120.00   1.00    0.43    --  107.75 -37.00 -60.00   85
 13  \w     93.00 178.00   1.00    0.43    --  107.75  57.00-120.00   85
 14  \w     93.00 172.00   1.00    0.43    --  107.75  57.00 150.00   79
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0299628000
_diffrn_orient_matrix_UB_12      -0.1107222000
_diffrn_orient_matrix_UB_13      -0.0016983000
_diffrn_orient_matrix_UB_21      -0.1258072000
_diffrn_orient_matrix_UB_22      -0.0278520000
_diffrn_orient_matrix_UB_23      -0.0497788000
_diffrn_orient_matrix_UB_31      -0.0140092000
_diffrn_orient_matrix_UB_32      0.0134804000
_diffrn_orient_matrix_UB_33      -0.1185935000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0480
_diffrn_reflns_av_unetI/netI     0.0478
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            11490
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        66.590
_diffrn_reflns_theta_max         66.590
_diffrn_reflns_theta_min         3.820
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.635
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.66404
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
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    1.293
_exptl_crystal_description       block
_exptl_crystal_F_000             868
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.614
_refine_diff_density_min         -0.442
_refine_diff_density_rms         0.078
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         3751
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0534
_refine_ls_R_factor_gt           0.0403
_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^)+(0.0553P)^2^+1.7784P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1001
_refine_ls_wR_factor_ref         0.1161
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3104
_reflns_number_total             3751
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0sc02162h2.cif
_cod_data_source_block           klb-2
_cod_database_code               1558372
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         CBN
_shelx_estimated_absorpt_t_max   0.621
_shelx_estimated_absorpt_t_min   0.505
_reflns_odcompleteness_completeness 99.03
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 N1-H1
 0.9 with sigma of 0.02
3.a Aromatic/amide H refined with riding coordinates:
 C5(H5), C11(H11), C3(H3), C20(H20), C9(H9), C18(H18), C4(H4)
3.b Idealised Me refined as rotating group:
 C14(H14a,H14b,H14c), C13(H13a,H13b,H13c), C22(H22a,H22b,H22c), C15(H15a,H15b,
 H15c), C24(H24a,H24b,H24c), C23(H23a,H23b,H23c)
;
_shelx_res_checksum              46958
_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 2.676
_oxdiff_exptl_absorpt_empirical_full_min 0.660