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_7133050
_publ_section_title
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 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         'C29 H10 B F15 N2, 1[CDCl3]'
_chemical_formula_sum            'C30 H11 B Cl3 F15 N2'
_chemical_formula_weight         801.57
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2024-03-13
_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                 109.205(4)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   34.981(5)
_cell_length_b                   9.9268(14)
_cell_length_c                   19.229(3)
_cell_measurement_reflns_used    4938
_cell_measurement_temperature    298.6
_cell_measurement_theta_max      19.494
_cell_measurement_theta_min      2.322
_cell_volume                     6305.7(16)
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_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    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      298.6
_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 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1178
_diffrn_reflns_av_unetI/netI     0.0938
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       41
_diffrn_reflns_limit_h_min       -41
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            35879
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        24.998
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_min         2.322
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_target            Mo
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.407
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5778
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1042 before and 0.0727 after correction.
The Ratio of minimum to maximum transmission is 0.7749.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.689
_exptl_crystal_description       block
_exptl_crystal_F_000             3168
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.506
_refine_diff_density_min         -0.542
_refine_diff_density_rms         0.070
_refine_ls_extinction_coef       0.0018(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   0.995
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     462
_refine_ls_number_reflns         5547
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      0.999
_refine_ls_R_factor_all          0.1762
_refine_ls_R_factor_gt           0.0770
_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^)+(0.1159P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1885
_refine_ls_wR_factor_ref         0.2212
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2520
_reflns_number_total             5547
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc01645a2.cif
_cod_data_source_block           mo_21oct10lp1_0m
_cod_depositor_comments
'Adding full bibliography for 7133047--7133054.cif.'
_cod_database_code               7133050
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.916
_shelx_estimated_absorpt_t_min   0.881
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C30) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
3.a Ternary CH refined with riding coordinates:
 C30(H30)
3.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B)
3.c Aromatic/amide H refined with riding coordinates:
 N2(H2), C6(H6), C3(H3), C5(H5), C4(H4)
3.d Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C)
;
_shelx_res_checksum              4954
_shelx_hkl_checksum              56622
_platon_squeeze_void_probe_radius 1.20
_olex2_submission_special_instructions 'No special instructions were received'