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_7160890
_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_formula_moiety         'C32 H26 B F2 N5 O, C H Cl3'
_chemical_formula_sum            'C33 H27 B Cl3 F2 N5 O'
_chemical_formula_weight         664.75
_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_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                 98.0047(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.8406(4)
_cell_length_b                   10.8382(2)
_cell_length_c                   18.0928(4)
_cell_measurement_reflns_used    9912
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      30.4106
_cell_measurement_theta_min      2.2735
_cell_volume                     3075.97(12)
_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 1.000
_diffrn_measured_fraction_theta_max 0.999
_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  0.0490
_diffrn_reflns_av_unetI/netI     0.0209
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            151022
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.533
_diffrn_reflns_theta_min         2.196
_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    0.347
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.7018
_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    1.435
_exptl_crystal_description       'flat ellipsoid'
_exptl_crystal_F_000             1368
_exptl_crystal_size_max          0.208
_exptl_crystal_size_mid          0.045
_exptl_crystal_size_min          0.029
_refine_diff_density_max         0.370
_refine_diff_density_min         -0.325
_refine_diff_density_rms         0.073
_refine_ls_extinction_coef       0.0073(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.175
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     523
_refine_ls_number_reflns         9403
_refine_ls_number_restraints     266
_refine_ls_restrained_S_all      1.176
_refine_ls_R_factor_all          0.0887
_refine_ls_R_factor_gt           0.0535
_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^)+(0.0612P)^2^+2.4519P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1308
_refine_ls_wR_factor_ref         0.1736
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6805
_reflns_number_total             9403
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob01628b2.cif
_cod_data_source_block           cmpd8a_AT037
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7160890
_shelx_shelxl_version_number     2019/3
_shelx_estimated_absorpt_t_min   0.931
_shelx_estimated_absorpt_t_max   0.990
_diffrn_source_source            'microfocus sealed tube'
_shelx_res_checksum              4174