Hetero Diels-Alder reactions of isolable <i>N</i>-borylenamines.
Liang, Pei; Wei, Junhui; Wei, Yongliang; Wang, Xue; Liu, Fei; Wang, Tongdao; Chemical communications (Cambridge, England) 60 (2024) 5964–5967; doi:10.1039/d4cc01645a

data_7133047
_publ_section_title
;
 Hetero Diels-Alder reactions of isolable <i>N</i>-borylenamines.
;
_journal_issue                   46
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              5964
_journal_page_last               5967
_journal_paper_doi               10.1039/d4cc01645a
_journal_volume                  60
_journal_year                    2024
_chemical_formula_moiety         'C35 H15 B F15 N O, 2[C6H14]'
_chemical_formula_sum            'C35 H15 B F15 N O'
_chemical_formula_weight         761.29
_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     iterative
_audit_creation_date             2023-12-26
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2024-04-08 deposited with the CCDC.	2024-05-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 105.2648(14)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.78652(15)
_cell_length_b                   21.7974(3)
_cell_length_c                   17.9089(2)
_cell_measurement_reflns_used    10371
_cell_measurement_temperature    300.15
_cell_measurement_theta_max      67.7410
_cell_measurement_theta_min      2.5590
_cell_volume                     4062.15(10)
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.3 (Bourhis et al., 2015)'
_diffrn_ambient_temperature      300.15
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 5.6
_diffrn_detector_type            'Bruker SMART CCD 6000 area detector'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART CCD 6000'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0191
_diffrn_reflns_av_unetI/netI     0.0221
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            21384
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.100
_diffrn_reflns_theta_min         3.264
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_target            Mo
_exptl_absorpt_coefficient_mu    1.097
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.245
_exptl_crystal_description       block
_exptl_crystal_F_000             1520
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.177
_refine_diff_density_min         -0.199
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     579
_refine_ls_number_reflns         7334
_refine_ls_number_restraints     147
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0558
_refine_ls_R_factor_gt           0.0494
_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^)+(0.0912P)^2^+0.8072P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1526
_refine_ls_wR_factor_ref         0.1576
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6030
_reflns_number_total             7334
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc01645a2.cif
_cod_data_source_block           ov_lp932-2_auto
_cod_depositor_comments
'Adding full bibliography for 7133047--7133054.cif.'
_cod_original_cell_volume        4062.16(9)
_cod_database_code               7133047
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.898
_shelx_estimated_absorpt_t_min   0.810
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 F48-C43 \\sim F1-C19
 with sigma of 0.02
 F49-C43 \\sim F2-C19
 with sigma of 0.04
 F50-C47 \\sim F5-C23
 with sigma of 0.02
 C47-C45 \\sim C23-C21
 with sigma of 0.04
 F51-C46 \\sim F4-C22
 with sigma of 0.02
 C9-C47 \\sim C9-C23
 with sigma of 0.04
 F52-C44 \\sim F3-C20
 with sigma of 0.04
 C9-C42 \\sim C9-C18
 with sigma of 0.02
 C42-C47 \\sim C18-C23
 with sigma of 0.02
 C42-C43 \\sim C18-C19
 with sigma of 0.02
 C42-C46 \\sim C18-C22
 with sigma of 0.04
 F49-C44 \\sim F2-C20
 with sigma of 0.02
 C46-C44 \\sim C22-C20
 with sigma of 0.04
 F52-C45 \\sim F3-C21
 with sigma of 0.02
 C47-C46 \\sim C23-C22
 with sigma of 0.02
 C9-C43 \\sim C9-C19
 with sigma of 0.04
 C46-C45 \\sim C22-C21
 with sigma of 0.02
 C42-C44 \\sim C18-C20
 with sigma of 0.04
 F49-C45 \\sim F2-C21
 with sigma of 0.04
 C43-C44 \\sim C19-C20
 with sigma of 0.02
 F52-C46 \\sim F3-C22
 with sigma of 0.04
 C45-C44 \\sim C21-C20
 with sigma of 0.02
 C47-C43 \\sim C23-C19
 with sigma of 0.04
 F48-C42 \\sim F1-C18
 with sigma of 0.04
 C43-C45 \\sim C19-C21
 with sigma of 0.04
 F48-C44 \\sim F1-C20
 with sigma of 0.04
 F50-C42 \\sim F5-C18
 with sigma of 0.04
 F50-C46 \\sim F5-C22
 with sigma of 0.04
 F51-C47 \\sim F4-C23
 with sigma of 0.04
 F51-C45 \\sim F4-C21
 with sigma of 0.04
3. Rigid body (RIGU) restrains
 C42, C43, C44, C45, C46, C47
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
 F1, C19, C23, F5, C20, F4, C22, C18, C21, F2, F3
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
4. Others
 Sof(H9)=Sof(F1)=Sof(F5)=Sof(F4)=Sof(C18)=Sof(F2)=Sof(F3)=Sof(C23)=Sof(C22)=
 Sof(C19)=Sof(C21)=Sof(C20)=1-FVAR(1)
 Sof(F48)=Sof(F50)=Sof(F51)=Sof(H13)=Sof(C42)=Sof(F49)=Sof(F52)=Sof(C47)=
 Sof(C46)=Sof(C43)=Sof(C45)=Sof(C44)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C9(H13), C9(H9)
5.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B)
5.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C6(H6), C17(H17), C13(H13A), C5(H5), C14(H14), C15(H15), C4(H4),
 C16(H16)
5.d Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C)
;
_smtbx_masks_special_details
;
A solvent mask was calculated and 364 electrons were 
found in a volume of 1332\%A^3^ in 1 void per unit cell. 
This is consistent with the presence of 
2[C6H14] per Asymmetric Unit 
which account for 400 electrons 
per unit cell.
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              32397
_shelx_hkl_checksum              27591
_shelx_fab_checksum              49843
_olex2_submission_special_instructions 'No special instructions were received'