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_1558375
_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         'C47 H46 B2 N4'
_chemical_formula_sum            'C47 H46 B2 N4'
_chemical_formula_weight         688.50
_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             2020-05-20
_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                 109.818(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.2493(3)
_cell_length_b                   26.0979(7)
_cell_length_c                   13.6593(4)
_cell_measurement_reflns_used    6707
_cell_measurement_temperature    172.98(10)
_cell_measurement_theta_max      76.3480
_cell_measurement_theta_min      3.3480
_cell_volume                     3772.64(19)
_computing_cell_refinement       'CrysAlisPro 1.171.39.30d (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.30d (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.30d (Rigaku OD, 2017)'
_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      172.98(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_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     39.00 102.00   1.00    3.50    --   48.45  81.00 131.00   63
  2  \w     82.00 165.00   1.00   27.00    --  106.49  81.00 131.00   83
  3  \w     92.00 178.00   1.00   27.00    --  106.49  57.00  60.00   86
  4  \w     41.00 131.00   1.00   27.00    --  106.49 -81.00   9.00   90
  5  \w     31.00  96.00   1.00    3.50    --   48.45-125.00-120.00   65
  6  \w     34.00  90.00   1.00   27.00    --  106.49 -99.00 -30.00   56
  7  \w     34.00 117.00   1.00   27.00    --  106.49-125.00-120.00   83
  8  \w     34.00  98.00   1.00   27.00    --  106.49 -99.00 -60.00   64
  9  \w     -7.00  19.00   1.00    3.50    --   48.45 -81.00   9.00   26
 10  \w    -73.00 -10.00   1.00    3.50    --  -48.45  81.00 131.00   63
 11  \w    -63.00 -35.00   1.00   27.00    --  -86.25  81.00 131.00   28
 12  \w   -120.00 -24.00   1.00    3.50    --  -48.45 -81.00   9.00   96
 13  \w   -119.00 -88.00   1.00    3.50    --  -48.45-125.00-180.00   31
 14  \w   -159.00-133.00   1.00   27.00    --  -86.25 -81.00   9.00   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      0.0875659000
_diffrn_orient_matrix_UB_12      -0.0169792000
_diffrn_orient_matrix_UB_13      -0.0596347000
_diffrn_orient_matrix_UB_21      -0.0817546000
_diffrn_orient_matrix_UB_22      -0.0481518000
_diffrn_orient_matrix_UB_23      -0.0384948000
_diffrn_orient_matrix_UB_31      -0.0827863000
_diffrn_orient_matrix_UB_32      0.0295623000
_diffrn_orient_matrix_UB_33      -0.0966636000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.710
_diffrn_reflns_av_R_equivalents  0.0449
_diffrn_reflns_av_unetI/netI     0.0455
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            21327
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         1.559
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.069
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81938
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.30d (Rigaku Oxford Diffraction, 2017)
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    1.212
_exptl_crystal_description       plate
_exptl_crystal_F_000             1464
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.332
_refine_diff_density_min         -0.253
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     527
_refine_ls_number_reflns         6608
_refine_ls_number_restraints     204
_refine_ls_restrained_S_all      1.018
_refine_ls_R_factor_all          0.0681
_refine_ls_R_factor_gt           0.0451
_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^)+(0.0563P)^2^+1.1220P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1068
_refine_ls_wR_factor_ref         0.1224
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4878
_reflns_number_total             6608
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0sc02162h2.cif
_cod_data_source_block           klb-3
_cod_original_cell_volume        3772.6(2)
_cod_database_code               1558375
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         CNB
_shelx_estimated_absorpt_t_max   0.997
_shelx_estimated_absorpt_t_min   0.966
_reflns_odcompleteness_completeness 99.02
_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
 C33A-C32A \\sim C33B-C32B \\sim C34B-C33B \\sim C34A-C33A \\sim C35A-C34A
\\sim C35B-C34B \\sim C36A-
 C35A \\sim C36B-C35B \\sim C36B-C31B \\sim C36A-C31A \\sim C32B-C31B \\sim
C32A-C31A
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
C31A \\sim C32A \\sim C33A \\sim C34A \\sim C35A \\sim C36A: within 2A with
sigma of 0.01 and sigma for terminal atoms of 0.02
C31B \\sim C32B \\sim C33B \\sim C34B \\sim C35B \\sim C36B: within 2A with
sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C31B) \\sim Ueq, Uanis(C32B) \\sim Ueq, Uanis(C33B) \\sim Ueq,
Uanis(C34B) \\sim Ueq, Uanis(C36A) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
Uanis(C31A) \\sim Ueq, Uanis(C32A) \\sim Ueq, Uanis(C33A) \\sim Ueq,
Uanis(C34A) \\sim Ueq, Uanis(C35B) \\sim Ueq, Uanis(C36B) \\sim Ueq: with sigma
of 0.01 and sigma for terminal atoms of 0.02
4. Others
 Sof(C31B)=Sof(C32B)=Sof(H32B)=Sof(C33B)=Sof(H33B)=Sof(C34B)=Sof(H34B)=
 Sof(C35B)=Sof(H35B)=Sof(C36B)=Sof(H36B)=1-FVAR(1)
 Sof(C31A)=Sof(C32A)=Sof(H32A)=Sof(C33A)=Sof(H33A)=Sof(C34A)=Sof(H34A)=
 Sof(C35A)=Sof(H35A)=Sof(C36A)=Sof(H36A)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C29(H29), C30(H30)
5.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C8(H8), C9(H9), C10(H10), C11(H11), C12(H12),
 C14(H14), C15(H15), C16(H16), C17(H17), C18(H18), C21(H21), C22(H22), C23(H23),
  C26(H26), C27(H27), C28(H28), C32B(H32B), C33B(H33B), C34B(H34B), C35B(H35B),
 C36B(H36B), C38(H38), C39(H39), C32A(H32A), C33A(H33A), C34A(H34A), C35A(H35A),
  C36A(H36A)
5.c Fitted hexagon refined as free rotating group:
 C31B(C32B,C33B,C34B,C35B,C36B)
5.d Idealised Me refined as rotating group:
 C41(H41a,H41b,H41c), C42(H42a,H42b,H42c), C43(H43a,H43b,H43c), C45(H45a,H45b,
 H45c), C46(H46a,H46b,H46c), C47(H47a,H47b,H47c)
;
_shelx_res_checksum              2418
_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 1.240
_oxdiff_exptl_absorpt_empirical_full_min 0.717