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_1558370
_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         '2(C18 H14 B Br N)'
_chemical_formula_sum            'C36 H28 B2 Br2 N2'
_chemical_formula_weight         670.04
_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   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                 108.694(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   18.5040(3)
_cell_length_b                   17.9348(3)
_cell_length_c                   19.6933(7)
_cell_measurement_reflns_used    9371
_cell_measurement_temperature    173.00(10)
_cell_measurement_theta_max      76.0510
_cell_measurement_theta_min      3.4760
_cell_volume                     6190.7(3)
_computing_cell_refinement       'CrysAlisPro 1.171.40.25a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.25a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.25a (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_environment      N~2~
_diffrn_ambient_temperature      173.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.982
_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    -86.00 -53.00   1.00    0.35    --  -48.45 113.00  99.00   33
  2  \w     23.00  86.00   1.00    0.35    --   48.45-113.00   7.00   63
  3  \w    -74.00 -49.00   1.00    1.40    --  -86.25 113.00  99.00   25
  4  \w   -132.00-102.00   1.00    1.40    --  -86.25-113.00   7.00   30
  5  \w     99.00 138.00   1.00    1.40    --  106.49 113.00  99.00   39
  6  \w     45.00 112.00   1.00    1.40    --  106.49-113.00   7.00   67
  7  \w   -108.00 -75.00   1.00    0.35    --  -48.45-125.00  30.00   33
  8  \w   -120.00 -72.00   1.00    0.35    --  -48.45-125.00 120.00   48
  9  \w    -61.00  27.00   1.00    0.35    --  -48.45  19.00-150.00   88
 10  \w     34.00 109.00   1.00    1.40    --  106.49 -99.00-150.00   75
 11  \w     36.00 120.00   1.00    1.40    --  106.49 -38.00-180.00   84
 12  \w     35.00 117.00   1.00    1.40    --  106.49-125.00-150.00   82
 13  \w     31.00 119.00   1.00    1.40    --  106.49 -19.00-180.00   88
;
_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      0.0681869000
_diffrn_orient_matrix_UB_12      -0.0498284000
_diffrn_orient_matrix_UB_13      0.0008381000
_diffrn_orient_matrix_UB_21      -0.0533168000
_diffrn_orient_matrix_UB_22      -0.0681836000
_diffrn_orient_matrix_UB_23      -0.0191374000
_diffrn_orient_matrix_UB_31      -0.0155835000
_diffrn_orient_matrix_UB_32      0.0157703000
_diffrn_orient_matrix_UB_33      -0.0802746000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0876
_diffrn_reflns_av_unetI/netI     0.0789
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            14639
_diffrn_reflns_point_group_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        66.582
_diffrn_reflns_theta_max         66.582
_diffrn_reflns_theta_min         3.418
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.526
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.55185
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.25a (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    1.438
_exptl_crystal_description       block
_exptl_crystal_F_000             2704
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.876
_refine_diff_density_min         -0.904
_refine_diff_density_rms         0.179
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.208
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     385
_refine_ls_number_reflns         5361
_refine_ls_number_restraints     14
_refine_ls_restrained_S_all      1.206
_refine_ls_R_factor_all          0.0871
_refine_ls_R_factor_gt           0.0730
_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^)+(0.1700P)^2^+4.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2095
_refine_ls_wR_factor_ref         0.2527
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4624
_reflns_number_total             5361
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0sc02162h2.cif
_cod_data_source_block           klb-1
_cod_database_code               1558370
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         BrNBC
_shelx_estimated_absorpt_t_max   0.719
_shelx_estimated_absorpt_t_min   0.418
_reflns_odcompleteness_completeness 97.96
_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 N(H) groups
2. Restrained distances
 N1-H1
 0.9 with sigma of 0.02
 N2-H2
 0.9 with sigma of 0.02
3. Rigid bond restraints
 C31, C32, C33, C34, C35, C36
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
4.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C8(H8), C9(H9), C10(H10), C11(H11), C12(H12),
 C18(H18), C17(H17), C16(H16), C15(H15), C14(H14), C21(H21), C22(H22), C23(H23),
  C30(H30), C29(H29), C28(H28), C27(H27), C26(H26), C32(H32), C33(H33),
 C34(H34), C35(H35), C36(H36)
;
_shelx_res_checksum              69536
_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 1.553
_oxdiff_exptl_absorpt_empirical_full_min 0.613