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_7134732
_publ_section_title
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 Development of electronically tuneable N-heterocyclic borates.
;
_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         'C12 H29 N P, C52 H80 B N4'
_chemical_formula_sum            'C64 H109 B N5 P'
_chemical_formula_weight         990.34
_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   mixed
_atom_sites_solution_primary     iterative
_audit_creation_date             2023-04-04
_audit_creation_method
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_audit_update_record
;
2025-03-17 deposited with the CCDC.	2025-06-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.591(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.1405(16)
_cell_length_b                   27.056(4)
_cell_length_c                   20.237(3)
_cell_measurement_reflns_used    9790
_cell_measurement_temperature    173.15
_cell_measurement_theta_max      72.55
_cell_measurement_theta_min      2.74
_cell_volume                     6615.7(16)
_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 0.993
_diffrn_measured_fraction_theta_max 0.979
_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  0.1125
_diffrn_reflns_av_unetI/netI     0.1131
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            46284
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.546
_diffrn_reflns_theta_min         2.735
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.642
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.5631
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1531 before and 0.1139 after correction.
The Ratio of minimum to maximum transmission is 0.7472.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    0.994
_exptl_crystal_description       Block
_exptl_crystal_F_000             2192
_exptl_crystal_size_max          0.377
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.076
_refine_diff_density_max         0.608
_refine_diff_density_min         -0.374
_refine_diff_density_rms         0.097
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     756
_refine_ls_number_reflns         12828
_refine_ls_number_restraints     122
_refine_ls_restrained_S_all      1.010
_refine_ls_R_factor_all          0.1214
_refine_ls_R_factor_gt           0.1031
_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=1/[\s^2^(Fo^2^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2582
_refine_ls_wR_factor_ref         0.2831
_reflns_Friedel_coverage         0.000
_reflns_number_gt                9361
_reflns_number_total             12828
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc01578b2.cif
_cod_data_source_block           '[H2NP(tBu)3][B(Py)4]_0m_a'
_cod_depositor_comments
'Adding full bibliography for 7134731--7134734.cif.'
_cod_original_cell_volume        6615.7(15)
_cod_database_code               7134732
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.953
_shelx_estimated_absorpt_t_min   0.794
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 H1A-N1 = H1B-N1
 0.87 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C71) \\sim Ueq, Uanis(C72) \\sim Ueq, Uanis(C54) \\sim Ueq, Uanis(C66)
\\sim Ueq, Uanis(C65) \\sim Ueq, Uanis(C64) \\sim Ueq, Uanis(C70) \\sim Ueq,
Uanis(C60) \\sim Ueq, Uanis(C59) \\sim Ueq, Uanis(C69) \\sim Ueq, Uanis(C57)
\\sim Ueq, Uanis(C68) \\sim Ueq, Uanis(C39) \\sim Ueq, Uanis(C38) \\sim Ueq,
Uanis(C21) \\sim Ueq, Uanis(C20) \\sim Ueq, Uanis(C24) \\sim Ueq, Uanis(C35)
\\sim Ueq, Uanis(C33) \\sim Ueq, Uanis(N1) \\sim Ueq: with sigma of 0.01 and
sigma for terminal atoms of 0.02
4. Others
 Sof(C64)=Sof(H64A)=Sof(H64B)=Sof(H64C)=Sof(C65)=Sof(H65A)=Sof(H65B)=Sof(H65C)=
 Sof(C66)=Sof(H66A)=Sof(H66B)=Sof(H66C)=1-FVAR(1)
 Sof(C61)=Sof(H61A)=Sof(H61B)=Sof(H61C)=Sof(C62)=Sof(H62A)=Sof(H62B)=Sof(H62C)=
 Sof(C63)=Sof(H63A)=Sof(H63B)=Sof(H63C)=FVAR(1)
 Sof(C68)=Sof(H68A)=Sof(H68B)=Sof(H68C)=Sof(C69)=Sof(H69A)=Sof(H69B)=Sof(H69C)=
 Sof(C70)=Sof(H70A)=Sof(H70B)=Sof(H70C)=1-FVAR(2)
 Sof(C57)=Sof(H57A)=Sof(H57B)=Sof(H57C)=Sof(C59)=Sof(H59A)=Sof(H59B)=Sof(H59C)=
 Sof(C60)=Sof(H60A)=Sof(H60B)=Sof(H60C)=FVAR(2)
 Sof(C71)=Sof(H71A)=Sof(H71B)=Sof(H71C)=Sof(C72)=Sof(H72A)=Sof(H72B)=Sof(H72C)=
 1-FVAR(3)
 Sof(C55)=Sof(H55A)=Sof(H55B)=Sof(H55C)=Sof(C56)=Sof(H56A)=Sof(H56B)=Sof(H56C)=
 FVAR(3)
5.a Riding coordinates:
 N1(H1A,H1B)
5.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C5(H5), C15(H15), C18(H18), C28(H28), C31(H31), C41(H41), C44(H44)
5.c Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C11(H11A,H11B,H11C),
 C12(H12A,H12B,H12C), C13(H13A,H13B,H13C), C20(H20A,H20B,H20C), C21(H21A,H21B,
 H21C), C22(H22A,H22B,H22C), C24(H24A,H24B,H24C), C25(H25A,H25B,H25C), C26(H26A,
 H26B,H26C), C33(H33A,H33B,H33C), C34(H34A,H34B,H34C), C35(H35A,H35B,H35C),
 C37(H37A,H37B,H37C), C38(H38A,H38B,H38C), C39(H39A,H39B,H39C), C46(H46A,H46B,
 H46C), C47(H47A,H47B,H47C), C48(H48A,H48B,H48C), C50(H50A,H50B,H50C), C51(H51A,
 H51B,H51C), C52(H52A,H52B,H52C), C54(H54A,H54B,H54C), C55(H55A,H55B,H55C),
 C56(H56A,H56B,H56C), C57(H57A,H57B,H57C), C59(H59A,H59B,H59C), C60(H60A,H60B,
 H60C), C61(H61A,H61B,H61C), C62(H62A,H62B,H62C), C63(H63A,H63B,H63C), C64(H64A,
 H64B,H64C), C65(H65A,H65B,H65C), C66(H66A,H66B,H66C), C71(H71A,H71B,H71C),
 C72(H72A,H72B,H72C), C68(H68A,H68B,H68C), C69(H69A,H69B,H69C), C70(H70A,H70B,
 H70C)
;
_shelx_res_checksum              96423
_shelx_hkl_checksum              95102
_olex2_submission_special_instructions 'No special instructions were received'