Reactivity of an aza-dipyrrin and an aza-BODIPY motif bearing two 2-pyridyl units: an emissive NNN binding pocket.
Gapare, Rosinah Liandrah; Diaz-Rodriguez, Roberto M; Williams, Victoria A.; Atwood, Mark; Cotnam, Michael J.; Hilborn, James W.; Johnson, Erin R.; Robertson, Katherine N.; Thompson, Alison; Organic & biomolecular chemistry 23 (2025) 10391–10397; doi:10.1039/d5ob01628b

data_7160891
_publ_section_title
;
 Reactivity of an aza-dipyrrin and an aza-BODIPY motif bearing two
 2-pyridyl units: an emissive NNN binding pocket.
;
_journal_issue                   45
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              10391
_journal_page_last               10397
_journal_paper_doi               10.1039/d5ob01628b
_journal_volume                  23
_journal_year                    2025
_chemical_absolute_configuration ad
_chemical_formula_moiety
;
2(C32 H26 B F2 N5 O), 0.5(C H2 Cl2), 0.5(C2 H6 O)
;
_chemical_formula_sum            'C65.5 H56 B2 Cl F4 N10 O2.5'
_chemical_formula_weight         1156.27
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_method           SHELXL-2019/3
_audit_update_record
;
2025-09-08 deposited with the CCDC.	2025-10-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.431(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.9104(5)
_cell_length_b                   12.0992(5)
_cell_length_c                   23.9514(11)
_cell_measurement_reflns_used    9893
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      26.3963
_cell_measurement_theta_min      2.3619
_cell_volume                     2840.9(2)
_computing_cell_refinement       'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_data_collection       'Bruker Instrument Service v8.5.0.11 RC8'
_computing_data_reduction        'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_structure_solution    'SHELXT-2014 (Sheldrick, 2015)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector                 '100 \\times 140 mm^2^ CMOS sensor'
_diffrn_detector_area_resol_mean 7.3910
_diffrn_detector_type            'Bruker PHOTON III'
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device       '\k--geometry diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_radiation_monochromator  'multilayer mirror'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1286
_diffrn_reflns_av_unetI/netI     0.0517
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            125139
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.350
_diffrn_reflns_theta_min         2.077
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_type              'Incoatec I\mS 3.0'
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    0.138
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6843
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
Krause, L., Herbst-Irmer, R., Sheldrick, G. M., Stalke, D. (2015).
J. Appl. Cryst. 48, 3-10.
;
_exptl_crystal_colour            orange-brown
_exptl_crystal_density_diffrn    1.352
_exptl_crystal_description       'rod (uncut)'
_exptl_crystal_F_000             1204
_exptl_crystal_size_max          0.289
_exptl_crystal_size_mid          0.026
_exptl_crystal_size_min          0.018
_refine_diff_density_max         0.192
_refine_diff_density_min         -0.219
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details
;
 Flack x determined using 3257 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.10(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     805
_refine_ls_number_reflns         10261
_refine_ls_number_restraints     41
_refine_ls_restrained_S_all      1.088
_refine_ls_R_factor_all          0.0752
_refine_ls_R_factor_gt           0.0571
_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^)+(0.0326P)^2^+1.8422P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1058
_refine_ls_wR_factor_ref         0.1133
_reflns_Friedel_coverage         0.898
_reflns_Friedel_fraction_full    0.987
_reflns_Friedel_fraction_max     0.986
_reflns_number_gt                8560
_reflns_number_total             10261
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob01628b2.cif
_cod_data_source_block           cmpd8b_AT038B
_cod_original_sg_symbol_H-M      'P 21'
_cod_original_formula_sum        'C65.50 H56 B2 Cl F4 N10 O2.50'
_cod_database_code               7160891
_shelx_shelxl_version_number     2019/3
_shelx_estimated_absorpt_t_min   0.961
_shelx_estimated_absorpt_t_max   0.998
_diffrn_source_source            'microfocus sealed tube'
_shelx_res_checksum              55282