Development of electronically tuneable N-heterocyclic borates.
Huerfano, I. J.; Gorobets, Evgueni; Zhou, Wen; Piers, Warren E.; Van Humbeck, Jeffrey F.; Derksen, Darren J.; Chemical communications (Cambridge, England) 61 (2025) 10610–10613; doi:10.1039/d5cc01578b

data_7134731
_publ_section_title
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 Development of electronically tuneable N-heterocyclic borates.
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_journal_issue                   57
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              10610
_journal_page_last               10613
_journal_paper_doi               10.1039/d5cc01578b
_journal_volume                  61
_journal_year                    2025
_chemical_formula_moiety         '2(Cl), 2(C32 H46 B N8), 2(C2.5 H5)'
_chemical_formula_sum            'C69 H102 B2 Cl2 N16'
_chemical_formula_weight         1248.18
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2025-04-30
_audit_creation_method
;
Olex2 1.5
(compiled 2025.04.05 svn.rf049d14d for OlexSys, GUI svn.r7224)
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_audit_update_record
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2025-04-30 deposited with the CCDC.	2025-06-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.393(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.6519(2)
_cell_length_b                   18.4389(4)
_cell_length_c                   28.0176(7)
_cell_measurement_reflns_used    4670
_cell_measurement_temperature    173.15
_cell_measurement_theta_max      72.19
_cell_measurement_theta_min      2.87
_cell_volume                     3935.58(17)
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_diffrn_ambient_temperature      173.15
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0853
_diffrn_reflns_av_unetI/netI     0.0839
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            27360
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.359
_diffrn_reflns_theta_min         2.873
_exptl_absorpt_coefficient_mu    1.098
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.6147
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1046 before and 0.0807 after correction.
The Ratio of minimum to maximum transmission is 0.8157.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.053
_exptl_crystal_description       Block
_exptl_crystal_F_000             1344
_exptl_crystal_size_max          0.319
_exptl_crystal_size_mid          0.097
_exptl_crystal_size_min          0.024
_refine_diff_density_max         1.207
_refine_diff_density_min         -0.375
_refine_diff_density_rms         0.094
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.117
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     589
_refine_ls_number_reflns         7719
_refine_ls_number_restraints     420
_refine_ls_restrained_S_all      1.129
_refine_ls_R_factor_all          0.1131
_refine_ls_R_factor_gt           0.0846
_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=exp[0.5000(sin\q/\l)^2^)]/[\s^2^(Fo^2^)+(0.1579P)^2^+0.2307P+0.5000] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2261
_refine_ls_wR_factor_ref         0.2568
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5278
_reflns_number_total             7719
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc01578b2.cif
_cod_data_source_block           '[H2B(Pm)4]Cl_0m_a'
_cod_depositor_comments
'Adding full bibliography for 7134731--7134734.cif.'
_cod_database_code               7134731
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.974
_shelx_estimated_absorpt_t_min   0.721
_olex2_refinement_description
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1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, H8 of N8, H7Z of N7, H3 of N3, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, H5 of N5, All C(H,H,H,H,H,H) groups
2. Restrained distances
 C47-C37 = C37-C39 = C39-C40 = C40-C38
 1.4 with sigma of 0.02
 C37-C40 = C38-C39
 2.2 with sigma of 0.01
 C30-C44 = C30-C45 = C30-C46 = C37-C50 = C50-C51 = C51-C52
 1.6 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
C31 \\sim C32 \\sim C33 \\sim C34 \\sim C35 \\sim C36 \\sim C22 \\sim C26 \\sim
C27 \\sim C24 \\sim C25 \\sim C19 \\sim C1 \\sim C28 \\sim C29 \\sim C41 \\sim
C42 \\sim C43: within 2A with sigma of 0.01 and sigma for terminal atoms of
0.02 within 2A
C44 \\sim C45 \\sim C46 \\sim C10 \\sim C20 \\sim C21: within 2A with sigma of
0.01 and sigma for terminal atoms of 0.02 within 2A
C38 \\sim C47 \\sim C37 \\sim C39 \\sim C40 \\sim C50 \\sim C51 \\sim C52:
within 2A with sigma of 0.01 and sigma for terminal atoms of 0.002 within 2A
Uanis(C31) \\sim Ueq, Uanis(C32) \\sim Ueq, Uanis(C33) \\sim Ueq, Uanis(C34)
\\sim Ueq, Uanis(C35) \\sim Ueq, Uanis(C36) \\sim Ueq, Uanis(C22) \\sim Ueq,
Uanis(C26) \\sim Ueq, Uanis(C27) \\sim Ueq, Uanis(C24) \\sim Ueq, Uanis(C25)
\\sim Ueq, Uanis(C19) \\sim Ueq, Uanis(C1) \\sim Ueq, Uanis(C28) \\sim Ueq,
Uanis(C29) \\sim Ueq, Uanis(C41) \\sim Ueq, Uanis(C42) \\sim Ueq, Uanis(C43)
\\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C44) \\sim Ueq, Uanis(C45) \\sim Ueq, Uanis(C46) \\sim Ueq, Uanis(C10)
\\sim Ueq, Uanis(C20) \\sim Ueq, Uanis(C21) \\sim Ueq: with sigma of 0.01 and
sigma for terminal atoms of 0.02
Uanis(C38) \\sim Ueq, Uanis(C47) \\sim Ueq, Uanis(C37) \\sim Ueq, Uanis(C39)
\\sim Ueq, Uanis(C40) \\sim Ueq, Uanis(C50) \\sim Ueq, Uanis(C51) \\sim Ueq,
Uanis(C52) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.002
Uanis(Cl1) \\sim Ueq, Uanis(N6) \\sim Ueq, Uanis(N1) \\sim Ueq: with sigma of
0.01 and sigma for terminal atoms of 0.02
4. Others
 Sof(C22)=Sof(H22A)=Sof(H22B)=Sof(H22C)=Sof(C32)=Sof(H32A)=Sof(H32B)=Sof(H32C)=
 Sof(C33)=Sof(H33A)=Sof(H33B)=Sof(H33C)=1-FVAR(1)
 Sof(C31)=Sof(H31A)=Sof(H31B)=Sof(H31C)=Sof(C26)=Sof(H26A)=Sof(H26B)=Sof(H26C)=
 Sof(C27)=Sof(H27A)=Sof(H27B)=Sof(H27C)=FVAR(1)
 Sof(H8)=Sof(C34)=Sof(H34A)=Sof(H34B)=Sof(H34C)=Sof(C35)=Sof(H35A)=Sof(H35B)=
 Sof(H35C)=Sof(C36)=Sof(H36A)=Sof(H36B)=Sof(H36C)=1-FVAR(2)
 Sof(H7Z)=Sof(C19)=Sof(H19A)=Sof(H19B)=Sof(H19C)=Sof(C24)=Sof(H24A)=Sof(H24B)=
 Sof(H24C)=Sof(C25)=Sof(H25A)=Sof(H25B)=Sof(H25C)=FVAR(2)
 Sof(H5)=Sof(C41)=Sof(H41A)=Sof(H41B)=Sof(H41C)=Sof(C42)=Sof(C43)=Sof(H43A)=
 Sof(H43B)=Sof(H43C)=1-FVAR(3)
 Sof(H42A)=Sof(H42B)=Sof(H42C)=Sof(H42D)=Sof(H42E)=Sof(H42F)=0.5*(1-FVAR(4))
 Sof(H3)=Sof(C1)=Sof(H1A)=Sof(H1B)=Sof(H1C)=Sof(C28)=Sof(H28A)=Sof(H28B)=
 Sof(H28C)=Sof(C29)=Sof(H29A)=Sof(H29B)=Sof(H29C)=FVAR(3)
 Sof(C44)=Sof(H44A)=Sof(H44B)=Sof(H44C)=Sof(C45)=Sof(H45A)=Sof(H45B)=Sof(H45C)=
 Sof(C46)=1-FVAR(4)
 Sof(H46A)=Sof(H46B)=Sof(H46C)=Sof(H46D)=Sof(H46E)=Sof(H46F)=0.5*(1-FVAR(5))
 Sof(C10)=Sof(H10A)=Sof(H10B)=Sof(H10C)=Sof(C20)=Sof(H20A)=Sof(H20B)=Sof(H20C)=
 Sof(C21)=Sof(H21A)=Sof(H21B)=Sof(H21C)=FVAR(4)
 Sof(C50)=Sof(H50A)=Sof(H50B)=Sof(C51)=Sof(H51A)=Sof(H51B)=Sof(C52)=Sof(H52A)=
 Sof(H52B)=Sof(H52C)=0.5*(1-FVAR(6))
 Sof(C38)=Sof(H38A)=Sof(H38B)=Sof(H38C)=Sof(C39)=Sof(H39A)=Sof(H39B)=Sof(C40)=
 Sof(H40A)=Sof(H40B)=0.5*FVAR(6)
 Fixed Sof: C37(0.5) C47(0.5) H47A(0.5) H47B(0.5) H47C(0.5)
5.a Secondary CH2 refined with riding coordinates:
 C50(H50A,H50B), C51(H51A,H51B), C39(H39A,H39B), C40(H40A,H40B)
5.b Aromatic/amide H refined with riding coordinates:
 C2(H2), N3(H3), C4(H4), N5(H5), N7(H7Z), C7(H7), N8(H8), C9(H9), C12(H12),
 C14(H14), C16(H16), C18(H18)
5.c Disordered Me refined with riding coordinates:
 C42(H42A,H42B,H42C,H42D,H42E,H42F), C46(H46A,H46B,H46C,H46D,H46E,H46F)
5.d Idealised Me refined as rotating group:
 C52(H52A,H52B,H52C), C31(H31A,H31B,H31C), C26(H26A,H26B,H26C), C27(H27A,H27B,
 H27C), C19(H19A,H19B,H19C), C24(H24A,H24B,H24C), C25(H25A,H25B,H25C), C1(H1A,
 H1B,H1C), C28(H28A,H28B,H28C), C29(H29A,H29B,H29C), C10(H10A,H10B,H10C),
 C20(H20A,H20B,H20C), C21(H21A,H21B,H21C), C38(H38A,H38B,H38C), C47(H47A,H47B,
 H47C), C22(H22A,H22B,H22C), C32(H32A,H32B,H32C), C33(H33A,H33B,H33C), C34(H34A,
 H34B,H34C), C35(H35A,H35B,H35C), C36(H36A,H36B,H36C), C41(H41A,H41B,H41C),
 C43(H43A,H43B,H43C), C44(H44A,H44B,H44C), C45(H45A,H45B,H45C)
;
_shelx_res_checksum              85523
_shelx_hkl_checksum              89772
_olex2_submission_special_instructions 'No special instructions were received'