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_1558374
_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         'C59 H70 B2 N4, C7 H8'
_chemical_formula_sum            'C66 H78 B2 N4'
_chemical_formula_weight         948.94
_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   geom
_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                 98.1553(9)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.75034(11)
_cell_length_b                   23.8044(3)
_cell_length_c                   19.95734(18)
_cell_measurement_reflns_used    14527
_cell_measurement_temperature    173.00(10)
_cell_measurement_theta_max      76.0010
_cell_measurement_theta_min      2.8590
_cell_volume                     5525.81(10)
_computing_cell_refinement       'CrysAlisPro 1.171.40.19a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.19a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.19a (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_type            HyPix
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_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    -63.00  24.00   1.00    0.11    --  -48.45  58.00 133.00   87
  2  \w    -10.00  43.00   1.00    0.11    --   48.45 -58.00  -7.00   53
  3  \w     83.00 110.00   1.00    0.11    --   48.45  58.00 133.00   27
  4  \w    -94.00 -62.00   1.00    0.90    --  -86.25  58.00 133.00   32
  5  \w   -139.00-114.00   1.00    0.90    --  -86.25 -58.00  -7.00   25
  6  \w    -50.00 -23.00   1.00    0.90    --  -86.25  58.00 133.00   27
  7  \w     91.00 178.00   1.00    0.90    --  106.49  58.00 133.00   87
  8  \w     36.00 122.00   1.00    0.90    --  106.49 -58.00  -7.00   86
  9  \w   -120.00 -78.00   1.00    0.11    --  -48.45-125.00 150.00   42
 10  \w   -119.00 -34.00   1.00    0.11    --  -48.45 -58.00  -7.00   85
 11  \w     34.00  92.00   1.00    0.90    --  106.49 -94.00 -60.00   58
 12  \w     34.00 108.00   1.00    0.90    --  106.49 -94.00 -30.00   74
 13  \w     93.00 178.00   1.00    0.90    --  106.49  15.00 -90.00   85
;
_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      -0.0864826000
_diffrn_orient_matrix_UB_12      -0.0203941000
_diffrn_orient_matrix_UB_13      -0.0603788000
_diffrn_orient_matrix_UB_21      -0.0552750000
_diffrn_orient_matrix_UB_22      -0.0394808000
_diffrn_orient_matrix_UB_23      0.0474448000
_diffrn_orient_matrix_UB_31      -0.0836086000
_diffrn_orient_matrix_UB_32      0.0471071000
_diffrn_orient_matrix_UB_33      0.0136757000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0359
_diffrn_reflns_av_unetI/netI     0.0352
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            31156
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        66.600
_diffrn_reflns_theta_max         66.600
_diffrn_reflns_theta_min         2.907
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.489
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.65582
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.19a (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.141
_exptl_crystal_description       plate
_exptl_crystal_F_000             2048
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.281
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     668
_refine_ls_number_reflns         9650
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.0568
_refine_ls_R_factor_gt           0.0440
_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^)+(0.0588P)^2^+2.0949P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1119
_refine_ls_wR_factor_ref         0.1211
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8200
_reflns_number_total             9650
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0sc02162h2.cif
_cod_data_source_block           klb-4
_cod_original_cell_volume        5525.81(9)
_cod_database_code               1558374
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         CBNBr
_shelx_estimated_absorpt_t_max   0.908
_shelx_estimated_absorpt_t_min   0.792
_reflns_odcompleteness_completeness 95.37
_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.a Ternary CH refined with riding coordinates:
 C35(H35), C52(H52), C55(H55)
2.b Aromatic/amide H refined with riding coordinates:
 C27(H27), C28(H28), C29(H29), C33(H33), C20(H20), C44(H44), C3(H3), C5(H5),
 C18(H18), C9(H9), C4(H4), C11(H11), C42(H42), C61(H61), C65(H65), C64(H64),
 C63(H63), C62(H62)
2.c Idealised Me refined as rotating group:
 C37(H37A,H37B,H37C), C22(H22A,H22B,H22C), C39(H39A,H39B,H39C), C53(H53A,H53B,
 H53C), C24(H24A,H24B,H24C), C47(H47A,H47B,H47C), C46(H46A,H46B,H46C), C54(H54A,
 H54B,H54C), C56(H56A,H56B,H56C), C58(H58A,H58B,H58C), C13(H13A,H13B,H13C),
 C59(H59A,H59B,H59C), C38(H38A,H38B,H38C), C23(H23A,H23B,H23C), C15(H15A,H15B,
 H15C), C14(H14A,H14B,H14C), C57(H57A,H57B,H57C), C48(H48A,H48B,H48C), C66(H66A,
 H66B,H66C)
;
_shelx_res_checksum              60978
_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 1.435
_oxdiff_exptl_absorpt_empirical_full_min 0.654