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_1574290
_publ_section_title
;
 Double helicene possessing B--N dative bonds built on
 1,4-dihydropyrrolo[3,2-b]pyrrole core
;
_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         'C76 H74 B2 N4 S2'
_chemical_formula_sum            'C76 H74 B2 N4 S2'
_chemical_formula_weight         1129.13
_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             2025-03-10
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2025-03-10 deposited with the CCDC.	2025-04-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 105.520(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.8961(5)
_cell_length_b                   23.8496(8)
_cell_length_c                   17.9551(6)
_cell_measurement_reflns_used    9349
_cell_measurement_temperature    130.00
_cell_measurement_theta_max      30.61
_cell_measurement_theta_min      2.50
_cell_volume                     6146.2(4)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_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    'olex2.solve 1.5 (Bourhis et al., 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  0.0401
_diffrn_reflns_av_unetI/netI     0.0231
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            96697
_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         25.499
_diffrn_reflns_theta_min         2.505
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.135
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6489
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0601 before and 0.0551 after correction.
The Ratio of minimum to maximum transmission is 0.8697.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.220
_exptl_crystal_description       prism
_exptl_crystal_F_000             2400
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.329
_refine_diff_density_min         -0.538
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1047
_refine_ls_number_reflns         11433
_refine_ls_number_restraints     46
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.0546
_refine_ls_R_factor_gt           0.0420
_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^)+(0.0500P)^2^+3.8867P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1026
_refine_ls_wR_factor_ref         0.1122
_reflns_Friedel_coverage         0.000
_reflns_number_gt                9486
_reflns_number_total             11433
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc00540j2.cif
_cod_data_source_block           mo_ac_wp_357a_130k_0m_a
_cod_depositor_comments
'Adding full bibliography for 1574289--1574290.cif.'
_cod_database_code               1574290
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.973
_shelx_estimated_absorpt_t_min   0.973
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C99-C98
 1.5 with sigma of 0.01
 C100-C99
 1.5 with sigma of 0.005
 C97-C98
 1.5 with sigma of 0.01
 C98-C100
 2.5 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
Uanis(C77) \\sim Ueq, Uanis(C78) \\sim Ueq, Uanis(C79) \\sim Ueq: with sigma of
0.005 and sigma for terminal atoms of 0.005
Uanis(C76) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.01
Uanis(C83) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.01
Uanis(C80) \\sim Ueq, Uanis(C97) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.01
4. Others
 Fixed Sof: C69(0.8) H69A(0.8) H69B(0.8) C85(0.8) H85A(0.8) H85B(0.8) C86(0.8)
 H86A(0.8) H86B(0.8) C87(0.8) H87A(0.8) H87B(0.8) C92(0.8) H92A(0.8) H92B(0.8)
 H92C(0.8) C70(0.8) H70A(0.8) H70B(0.8) C73(0.8) H73A(0.8) H73B(0.8) C91(0.8)
 H91A(0.8) H91B(0.8) C71(0.8) H71A(0.8) H71B(0.8) C90(0.8) H90A(0.8) H90B(0.8)
 C72(0.8) H72A(0.8) H72B(0.8) C89(0.8) H89A(0.8) H89B(0.8) C88(0.8) H88A(0.8)
 H88B(0.8) C74(0.8) H74A(0.8) H74B(0.8) C75(0.8) H75A(0.8) H75B(0.8) C83(0.2)
 H83A(0.2) H83B(0.2) C81(0.2) H81A(0.2) H81B(0.2) C76(0.8) H76A(0.8) H76B(0.8)
 H76C(0.8) C82(0.2) H82A(0.2) H82B(0.2) C79(0.2) H79A(0.2) H79B(0.2) C78(0.2)
 H78A(0.2) H78B(0.2) C84(0.2) H84A(0.2) H84B(0.2) H84C(0.2) C80(0.2) H80A(0.2)
 H80B(0.2) C77(0.2) H77A(0.2) H77B(0.2) C94(0.2) H94A(0.2) H94B(0.2) C96(0.2)
 H96A(0.2) H96B(0.2) C97(0.2) H97A(0.2) H97B(0.2) C93(0.2) H93A(0.2) H93B(0.2)
 C95(0.2) H95A(0.2) H95B(0.2) C99(0.2) H99A(0.2) H99B(0.2) C98(0.2) H98A(0.2)
 H98B(0.2) C100(0.2) H10A(0.2) H10B(0.2) H10C(0.2)
 Fixed Uiso: C99(0.08) C98(0.08) C100(0.08)
5.a Secondary CH2 refined with riding coordinates:
 C69(H69A,H69B), C85(H85A,H85B), C86(H86A,H86B), C87(H87A,H87B), C70(H70A,
 H70B), C73(H73A,H73B), C91(H91A,H91B), C71(H71A,H71B), C90(H90A,H90B),
 C72(H72A,H72B), C89(H89A,H89B), C88(H88A,H88B), C74(H74A,H74B), C75(H75A,H75B),
  C83(H83A,H83B), C81(H81A,H81B), C82(H82A,H82B), C79(H79A,H79B), C78(H78A,
 H78B), C80(H80A,H80B), C77(H77A,H77B), C94(H94A,H94B), C96(H96A,H96B),
 C97(H97A,H97B), C93(H93A,H93B), C95(H95A,H95B), C99(H99A,H99B), C98(H98A,H98B)
5.b Idealised Me refined as rotating group:
 C92(H92A,H92B,H92C), C76(H76A,H76B,H76C), C84(H84A,H84B,H84C), C100(H10A,H10B,
 H10C)
;
_shelx_res_checksum              29711
_olex2_submission_special_instructions 'No special instructions were received'