Metal-free and visible photons for the dehydrogenative N-N coupling of amines: Powerful methods to optoelectronic materials
Li, Linjie; Shang, Yunyi; Gao, Yujia; Zhang, Yanfeng; Xu, Chao; Zhang, Qichun; Wang, Hui; Green Chemistry  (2026) –; doi:10.1039/D5GC04907E

data_7251404
_publ_section_title
;
 Metal-free and visible photons for the dehydrogenative N-N coupling of
 amines: Powerful methods to optoelectronic materials
;
_journal_name_full               'Green Chemistry'
_journal_paper_doi               10.1039/D5GC04907E
_journal_year                    2026
_chemical_formula_moiety         'C24 H12 Br4 N2'
_chemical_formula_sum            'C24 H12 Br4 N2'
_chemical_formula_weight         648.00
_chemical_name_systematic        2a
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2025-08-11
_audit_creation_method
;
Olex2 1.5
(compiled 2025.07.13 svn.rb7424aed for OlexSys, GUI svn.r7314)
;
_audit_update_record
;
2025-09-16 deposited with the CCDC.	2025-12-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   10.5240(3)
_cell_length_b                   15.0537(5)
_cell_length_c                   27.8000(8)
_cell_measurement_reflns_used    9732
_cell_measurement_temperature    230.15
_cell_measurement_theta_max      68.25
_cell_measurement_theta_min      3.34
_cell_volume                     4404.2(2)
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      230.15
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_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  0.0471
_diffrn_reflns_av_unetI/netI     0.0178
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            63304
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.313
_diffrn_reflns_theta_min         3.179
_diffrn_source_current           50.0
_diffrn_source_power             2.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    9.030
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.4687
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1132 before and 0.0646 after correction.
The Ratio of minimum to maximum transmission is 0.6224.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.955
_exptl_crystal_description       block
_exptl_crystal_F_000             2480
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: n-hexane /DCM (2:1, v/v)'
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         1.352
_refine_diff_density_min         -1.590
_refine_diff_density_rms         0.104
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.107
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         4001
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.107
_refine_ls_R_factor_all          0.0359
_refine_ls_R_factor_gt           0.0351
_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^)+(0.0366P)^2^+11.0320P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0845
_refine_ls_wR_factor_ref         0.0851
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3906
_reflns_number_total             4001
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5gc04907e2.cif
_cod_data_source_block           s_pl
_cod_original_sg_symbol_H-M      Pbca
_cod_database_code               7251404
_shelx_shelxl_version_number     2019/2
_shelx_estimated_absorpt_t_max   0.465
_shelx_estimated_absorpt_t_min   0.173
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C7(H7), C8(H8), C9(H9), C10(H10), C13(H13), C14(H14),
 C17(H17), C20(H20), C22(H22), C23(H23)
;
_shelx_res_checksum              50514
_olex2_submission_special_instructions 'No special instructions were received'