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_1558376
_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(C19 H29 B N O2)'
_chemical_formula_sum            'C38 H58 B2 N2 O4'
_chemical_formula_weight         628.48
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-06-09
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-06-09 deposited with the CCDC.	2020-06-19 downloaded from the CCDC.
;
_cell_angle_alpha                76.803(10)
_cell_angle_beta                 82.173(9)
_cell_angle_gamma                68.411(11)
_cell_formula_units_Z            1
_cell_length_a                   9.0716(10)
_cell_length_b                   9.8412(13)
_cell_length_c                   11.5149(12)
_cell_measurement_reflns_used    2294
_cell_measurement_temperature    172.99(10)
_cell_measurement_theta_max      75.3730
_cell_measurement_theta_min      3.9370
_cell_volume                     929.1(2)
_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  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      172.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.923
_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    -61.00  21.00   1.00    0.55    --  -48.45  38.00  90.00   82
  2  \w    -84.00   1.00   1.00    0.55    --  -48.45 109.00 -24.00   85
  3  \w     28.00  69.00   1.00    0.55    --   48.45-109.00-119.00   41
  4  \w     14.00  61.00   1.00    0.55    --   48.45 -38.00-150.00   47
  5  \w     69.00 108.00   1.00    4.00    --  106.49-109.00-119.00   39
  6  \w     35.00 129.00   1.00    4.00    --  106.49 -77.00-180.00   94
  7  \w    153.00 178.00   1.00    4.00    --  106.49  57.00-120.00   25
  8  \w    101.00 145.00   1.00    4.00    --  106.49 109.00 -24.00   44
  9  \w     92.00 141.00   1.00    4.00    --  106.49  57.00-120.00   49
 10  \w     94.00 174.00   1.00    4.00    --  106.49  57.00  60.00   80
 11  \w    152.00 178.00   1.00    4.00    --  106.49  19.00 150.00   26
 12  \w     94.00 164.00   1.00    4.00    --  106.49 125.00  90.00   70
 13  \w     94.00 149.00   1.00    4.00    --  106.49  19.00 150.00   55
 14  \w     74.00 114.00   1.00    4.00    --  106.49-125.00  60.00   40
 15  \w     34.00  69.00   1.00    4.00    --  106.49-125.00  60.00   35
 16  \w     34.00 109.00   1.00    4.00    --  106.49 -99.00  60.00   75
 17  \w     43.00 104.00   1.00    4.00    --  106.49 -99.00 150.00   61
 18  \w    -20.00  11.00   1.00    0.55    --   48.45 -38.00-150.00   31
 19  \w   -109.00 -71.00   1.00    0.55    --  -48.45-125.00  60.00   38
 20  \w   -120.00 -89.00   1.00    4.00    --  -86.25 -99.00  30.00   31
 21  \w   -125.00 -85.00   1.00    4.00    --  -86.25 -99.00 -30.00   40
 22  \w   -120.00 -79.00   1.00    4.00    --  -86.25-109.00-119.00   41
 23  \w   -111.00 -77.00   1.00    0.55    --  -48.45-125.00 -90.00   34
 24  \w   -154.00-127.00   1.00    4.00    --  -86.25 -99.00  30.00   27
 25  \w   -153.00-128.00   1.00    4.00    --  -86.25 -99.00 -30.00   25
 26  \w    -83.00 -57.00   1.00    4.00    --  -86.25 109.00 -24.00   26
;
_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      -0.0600897000
_diffrn_orient_matrix_UB_12      -0.1078883000
_diffrn_orient_matrix_UB_13      -0.0410600000
_diffrn_orient_matrix_UB_21      0.0098008000
_diffrn_orient_matrix_UB_22      -0.0928196000
_diffrn_orient_matrix_UB_23      0.1279131000
_diffrn_orient_matrix_UB_31      -0.1725094000
_diffrn_orient_matrix_UB_32      0.0958581000
_diffrn_orient_matrix_UB_33      0.0299832000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0532
_diffrn_reflns_av_unetI/netI     0.0667
_diffrn_reflns_Laue_measured_fraction_full 0.979
_diffrn_reflns_Laue_measured_fraction_max 0.923
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8347
_diffrn_reflns_point_group_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.923
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.405
_diffrn_reflns_theta_min         3.950
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.549
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80333
_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    1.123
_exptl_crystal_description       block
_exptl_crystal_F_000             342
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.409
_refine_diff_density_min         -0.347
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     434
_refine_ls_number_reflns         3616
_refine_ls_number_restraints     1042
_refine_ls_restrained_S_all      1.018
_refine_ls_R_factor_all          0.1119
_refine_ls_R_factor_gt           0.0803
_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^)+(0.0473P)^2^+1.2321P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1902
_refine_ls_wR_factor_ref         0.2121
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2685
_reflns_number_total             3616
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0sc02162h2.cif
_cod_data_source_block           klb-7
_cod_database_code               1558376
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.853
_shelx_estimated_absorpt_t_min   0.810
_reflns_odcompleteness_completeness 98.40
_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
 C8A-C7 \\sim C8B-C7 \\sim C9B-C7 \\sim C9A-C7 \\sim C7-C10B \\sim C7-C10A
\\sim C17A-C15 \\sim C16B-C15
 with sigma of 0.02
 C16A-C15 \\sim C17B-C15 \\sim C18A-C15 \\sim C18B-C15 \\sim C13B-C11 \\sim
C13A-C11 \\sim C14A-C11
 with sigma of 0.02
 C14B-C11 \\sim C12A-C11 \\sim C12B-C11
 with sigma of 0.02
 C19-O2 \\sim C20-O4
 with sigma of 0.01
 C1-B1 \\sim C1-B1A
 with sigma of 0.01
3. Restrained planarity
 B1, O1, C19, N1, N2, C20, O2, O3, O4, B2, C1
 with sigma of 0.01
 B1A, O1A, C19A, N1A, N2A, C20A, O2A, O3A, O4A, B2A, C1
 with sigma of 0.01
4. Uiso/Uaniso restraints and constraints
C7 \\sim C8A \\sim C9A \\sim C10A \\sim C8B \\sim C9B \\sim C10B \\sim C11
\\sim C12A \\sim C13A \\sim C14A \\sim C12B \\sim C13B \\sim C14B \\sim C15
\\sim C16A \\sim C17A \\sim C18A \\sim C16B \\sim C17B \\sim C18B: within 2A
with sigma of 0.01 and sigma for terminal atoms of 0.02
B1 \\sim O1 \\sim C19 \\sim N1 \\sim N2 \\sim C20 \\sim O2 \\sim O3 \\sim O4
\\sim B2 \\sim B1A \\sim O1A \\sim C19A \\sim N1A \\sim N2A \\sim C20A \\sim
O2A \\sim O3A \\sim O4A \\sim B2A: within 2A with sigma of 0.01 and sigma for
terminal atoms of 0.02
Uanis(B1) \\sim Ueq, Uanis(O1) \\sim Ueq, Uanis(C19) \\sim Ueq, Uanis(N1) \\sim
Ueq, Uanis(N2) \\sim Ueq, Uanis(C20) \\sim Ueq, Uanis(O2) \\sim Ueq, Uanis(O3)
\\sim Ueq, Uanis(O4) \\sim Ueq, Uanis(B2) \\sim Ueq, Uanis(B1A) \\sim Ueq,
Uanis(O1A) \\sim Ueq, Uanis(C19A) \\sim Ueq, Uanis(N1A) \\sim Ueq, Uanis(N2A)
\\sim Ueq, Uanis(C20A) \\sim Ueq, Uanis(O2A) \\sim Ueq, Uanis(O3A) \\sim Ueq,
Uanis(O4A) \\sim Ueq, Uanis(B2A) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
5. Rigid body (RIGU) restrains
 B1, O1, C19, N1, N2, C20, O2, O3, O4, B2, B1A, O1A, C19A, N1A, N2A, C20A, O2A,
  O3A, O4A, B2A, C7, C8A, C9A, C10A, C8B, C9B, C10B, C11, C12A, C13A, C14A,
 C12B, C13B, C14B, C15, C16A, C17A, C18A, C16B, C17B, C18B
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
6. Same fragment restrains
{B1, O1, C19, N1, N2, C20, O2, O3, O4, B2} sigma for 1-2: 0.01, 1-3: 0.04
as
{B1A, O1A, C19A, N1A, N2A, C20A, O2A, O3A, O4A, B2A}
7. Others
 Sof(C8B)=Sof(H8BA)=Sof(H8BB)=Sof(H8BC)=Sof(C9B)=Sof(H9BA)=Sof(H9BB)=Sof(H9BC)=
 Sof(C10B)=Sof(H10D)=Sof(H10E)=Sof(H10F)=1-FVAR(1)
 Sof(C8A)=Sof(H8AA)=Sof(H8AB)=Sof(H8AC)=Sof(C9A)=Sof(H9AA)=Sof(H9AB)=Sof(H9AC)=
 Sof(C10A)=Sof(H10A)=Sof(H10B)=Sof(H10C)=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)
 Sof(B1A)=Sof(O1A)=Sof(C19A)=Sof(N1A)=Sof(N2A)=Sof(C20A)=Sof(O2A)=Sof(O3A)=
 Sof(O4A)=Sof(B2A)=0.5*(1-FVAR(5))
 Sof(B1)=Sof(O1)=Sof(C19)=Sof(N1)=Sof(N2)=Sof(C20)=Sof(O2)=Sof(O3)=Sof(O4)=
 Sof(B2)=0.5*FVAR(5)
8.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5)
8.b Fitted hexagon refined as free rotating group:
 C1(C2,C3,C4,C5,C6)
8.c Idealised Me refined as rotating group:
 C8A(H8AA,H8AB,H8AC), C9A(H9AA,H9AB,H9AC), C10A(H10A,H10B,H10C), C8B(H8BA,H8BB,
 H8BC), C9B(H9BA,H9BB,H9BC), C10B(H10D,H10E,H10F), C12A(H12A,H12B,H12C),
 C13A(H13A,H13B,H13C), C14A(H14A,H14B,H14C), C12B(H12D,H12E,H12F), C13B(H13D,
 H13E,H13F), C14B(H14D,H14E,H14F), C16A(H16A,H16B,H16C), C17A(H17A,H17B,H17C),
 C18A(H18A,H18B,H18C), C16B(H16D,H16E,H16F), C17B(H17D,H17E,H17F), C18B(H18D,
 H18E,H18F)
;
_shelx_res_checksum              10839
_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 1.644
_oxdiff_exptl_absorpt_empirical_full_min 0.324