Double helicene possessing B–N dative bonds built on 1,4-dihydropyrrolo[3,2-b]pyrrole core
Petrykowski, Wojciech D.; Vanthuyne, Nicolas; Naim, Carmelo; Bertocchi, Francesco; Poronik, Yevgen M.; Ciesielski, Arkadiusz; Cyrański, Michał K.; Terenziani, Francesca; Jacquemin, Denis; Gryko, Daniel T.; Chemical Science 16 (2025) 8338–8345; doi:10.1039/D5SC00540J

data_1574289
_publ_section_title
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 Double helicene possessing B--N dative bonds built on
 1,4-dihydropyrrolo[3,2-b]pyrrole core
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_journal_issue                   19
_journal_name_full               'Chemical Science'
_journal_page_first              8338
_journal_page_last               8345
_journal_paper_doi               10.1039/D5SC00540J
_journal_volume                  16
_journal_year                    2025
_chemical_formula_moiety         'C72 H73.999 B2 N4'
_chemical_formula_sum            'C72 H74 B2 N4'
_chemical_formula_weight         1016.97
_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     dual
_audit_creation_date             2024-12-30
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
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2025-01-08 deposited with the CCDC.	2025-04-02 downloaded from the CCDC.
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_cell_angle_alpha                90
_cell_angle_beta                 106.520(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   20.2478(10)
_cell_length_b                   12.0654(6)
_cell_length_c                   24.4100(12)
_cell_measurement_reflns_used    9726
_cell_measurement_temperature    130(2)
_cell_measurement_theta_max      30.19
_cell_measurement_theta_min      2.64
_cell_volume                     5717.1(5)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_temperature      130.00
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0516
_diffrn_reflns_av_unetI/netI     0.0390
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            63992
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.000
_diffrn_reflns_theta_min         2.522
_exptl_absorpt_coefficient_mu    0.068
_exptl_absorpt_correction_T_max  0.993
_exptl_absorpt_correction_T_min  0.984
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            'clear yellowish'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_density_diffrn    1.182
_exptl_crystal_description       needle
_exptl_crystal_F_000             2176
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.434
_refine_diff_density_min         -0.397
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       0.0009(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   1.045
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     956
_refine_ls_number_reflns         11218
_refine_ls_number_restraints     1051
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0751
_refine_ls_R_factor_gt           0.0520
_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^)+(0.0644P)^2^+3.2775P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1291
_refine_ls_wR_factor_ref         0.1430
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8370
_reflns_number_total             11218
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc00540j2.cif
_cod_data_source_block           mo_wp_230_130k_0m
_cod_depositor_comments
'Adding full bibliography for 1574289--1574290.cif.'
_cod_database_code               1574289
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.993
_shelx_estimated_absorpt_t_min   0.973
_olex2_refinement_description
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1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, All C(H,H,H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Shared sites
{C60B, C60C}
3. Restrained distances
 C59-C60A = C60A-C61A = C61A-C62A = C62A-C63A = C63A-C64A = C64A-C65A
 1.52 with sigma of 0.01
 C59-C60B = C60B-C61B = C61B-C62B = C62B-C63B = C63B-C64B = C64B-C65B
 1.52 with sigma of 0.01
 C59-C60C = C60C-C61C = C61C-C62C = C62C-C63C = C63C-C64C = C64C-C65C
 1.52 with sigma of 0.01
 C24-C25A = C25A-C26A = C26A-C27 = C24-C25B = C25B-C26B = C26B-C27 = C24-C25C =
  C25C-C26C = C26C-C27
 1.52 with sigma of 0.02
 C58-C60A = C59-C61A = C60A-C62A = C61A-C63A = C62A-C64A = C63A-C65A
 2.54 with sigma of 0.02
 C58-C60B = C59-C61B = C60B-C62B = C61B-C63B = C62B-C64B = C63B-C65B
 2.54 with sigma of 0.02
 C58-C60C = C59-C61C = C60C-C62C = C61C-C63C = C62C-C64C = C63C-C65C
 2.54 with sigma of 0.02
 C23-C25A = C24-C26A = C25A-C27 = C26A-C28
 2.54 with sigma of 0.04
4. Uiso/Uaniso restraints and constraints
C60A \\sim C61A \\sim C62A \\sim C63A \\sim C64A \\sim C65A \\sim C60B \\sim
C61B \\sim C62B \\sim C63B \\sim C64B \\sim C65B \\sim C60C \\sim C61C \\sim
C62C \\sim C63C \\sim C64C \\sim C65C: within 8A with sigma of 0.02 and sigma
for terminal atoms of 0.04 within 8A
C25A \\sim C26A \\sim C25B \\sim C26B \\sim C25C \\sim C26C: within 2A with
sigma of 0.02 and sigma for terminal atoms of 0.04 within 2A
Uanis(C60B) = Uanis(C60C)
5. Others
 Fixed Sof: H24B(0.58608) H24A(0.58608) H24D(0.213) H24C(0.213) H24F(0.20091)
 H24E(0.20091) C25A(0.58608) H25A(0.58608) H25B(0.58608) C26A(0.58608)
 H26A(0.58608) H26B(0.58608) C25B(0.213) H25C(0.213) H25D(0.213) C26B(0.213)
 H26C(0.213) H26D(0.213) C25C(0.20091) H25E(0.20091) H25F(0.20091)
 C26C(0.20091) H26E(0.20091) H26F(0.20091) H27B(0.58608) H27A(0.58608)
 H27C(0.213) H27D(0.213) H27F(0.20091) H27E(0.20091) H59A(0.36918)
 H59B(0.36918) H59C(0.31358) H59D(0.31358) H59E(0.31719) H59F(0.31719)
 C60A(0.36918) H60A(0.36918) H60B(0.36918) C61A(0.36918) H61A(0.36918)
 H61B(0.36918) C62A(0.36918) H62A(0.36918) H62B(0.36918) C63A(0.36918)
 H63A(0.36918) H63B(0.36918) C64A(0.36918) H64A(0.36918) H64B(0.36918)
 C65A(0.36918) H65A(0.36918) H65B(0.36918) H65C(0.36918) C60B(0.31358)
 H60C(0.31358) H60D(0.31358) C61B(0.31358) H61C(0.31358) H61D(0.31358)
 C62B(0.31358) H62C(0.31358) H62D(0.31358) C63B(0.31358) H63C(0.31358)
 H63D(0.31358) C64B(0.31358) H64C(0.31358) H64D(0.31358) C65B(0.31358)
 H65D(0.31358) H65E(0.31358) H65F(0.31358) C60C(0.31719) H60E(0.31719)
 H60F(0.31719) C61C(0.31719) H61E(0.31719) H61F(0.31719) C62C(0.31719)
 H62E(0.31719) H62F(0.31719) C63C(0.31719) H63E(0.31719) H63F(0.31719)
 C64C(0.31719) H64E(0.31719) H64F(0.31719) C65C(0.31719) H65G(0.31719)
 H65H(0.31719) H65I(0.31719)
6.a Secondary CH2 refined with riding coordinates:
 C22(H22A,H22B), C23(H23A,H23B), C24(H24B,H24A), C24(H24D,H24C), C24(H24F,
 H24E), C25A(H25A,H25B), C26A(H26A,H26B), C25B(H25C,H25D), C26B(H26C,H26D),
 C25C(H25E,H25F), C26C(H26E,H26F), C27(H27B,H27A), C27(H27C,H27D), C27(H27F,
 H27E), C28(H28A,H28B), C58(H58A,H58B), C59(H59A,H59B), C59(H59C,H59D),
 C59(H59E,H59F), C60A(H60A,H60B), C61A(H61A,H61B), C62A(H62A,H62B), C63A(H63A,
 H63B), C64A(H64A,H64B), C60B(H60C,H60D), C61B(H61C,H61D), C62B(H62C,H62D),
 C63B(H63C,H63D), C64B(H64C,H64D), C60C(H60E,H60F), C61C(H61E,H61F), C62C(H62E,
 H62F), C63C(H63E,H63F), C64C(H64E,H64F)
6.b Me refined with riding coordinates:
 C65A(H65A,H65B,H65C), C65B(H65D,H65E,H65F), C65C(H65G,H65H,H65I)
6.c Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C8(H8A,H8B,H8C), C29(H29A,H29B,H29C), C43(H43A,H43B,H43C),
 C44(H44A,H44B,H44C)
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_shelx_res_checksum              30871
_olex2_submission_special_instructions 'No special instructions were received'