Sub-<i>m</i>-benziporphyrin: a subcarbaporphyrinoid and its B<sup>III</sup> complex with an unprecedented planar tridentate 14π-aromatic network.
Liu, Le; Song, Shuangji; Lee, Jiyeon; Rao, Yutao; Xu, Ling; Zhou, Mingbo; Yin, Bangshao; Oh, Juwon; Kim, Jiwon; Osuka, Atsuhiro; Song, Jianxin; Chemical science 16 (2025) 1155–1160; doi:10.1039/d4sc07199a

data_1573431
_publ_section_title
;
 Sub-<i>m</i>-benziporphyrin: a subcarbaporphyrinoid and its
 B<sup>III</sup> complex with an unprecedented planar tridentate
 14&#x3c0;-aromatic network.
;
_journal_issue                   3
_journal_name_full               'Chemical science'
_journal_page_first              1155
_journal_page_last               1160
_journal_paper_doi               10.1039/d4sc07199a
_journal_volume                  16
_journal_year                    2025
_chemical_formula_moiety         'C49 H39 B N2 O2'
_chemical_formula_sum            'C49 H39 B N2 O2'
_chemical_formula_weight         698.63
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2023-12-01
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2024-08-25 deposited with the CCDC.	2024-12-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 114.86(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.211(2)
_cell_length_b                   20.856(2)
_cell_length_c                   15.732(3)
_cell_measurement_reflns_used    2627
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      71.3740
_cell_measurement_theta_min      3.7130
_cell_volume                     3933.0(12)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0697
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -97.00 -70.00   1.00    6.00    --  -34.73 -57.00 120.00   27
  2  \w    -68.00 -18.00   1.00    6.00    --  -34.73 -57.00 120.00   50
  3  \w     24.00  78.00   1.00    6.00    --   34.73-125.00 -60.00   54
  4  \w     25.00  83.00   1.00    6.00    --   34.73-125.00  60.00   58
  5  \w     37.00  76.00   1.00    6.00    --   34.73-125.00-180.00   39
  6  \w     94.00 126.00   1.00   30.00    --  105.25 -30.00  30.00   32
  7  \w     49.00  87.00   1.00   30.00    --  105.25 -30.00  30.00   38
  8  \w     81.00 167.00   1.00   30.00    --  105.25  77.00  60.00   86
  9  \w    114.00 157.00   1.00   30.00    --  105.25  30.00 -60.00   43
 10  \w     89.00 172.00   1.00   30.00    --  105.25  77.00-180.00   83
 11  \w    -25.00  54.00   1.00    6.00    --   34.73 -38.00 -90.00   79
 12  \w    -21.00  13.00   1.00    6.00    --   34.73 -38.00  60.00   34
 13  \w     21.00 102.00   1.00    6.00    --   34.73  57.00-120.00   81
 14  \w     63.00  88.00   1.00    6.00    --   34.73-125.00-120.00   25
 15  \w    -32.00  -3.00   1.00    6.00    --   34.73 -57.00-180.00   29
 16  \w    -34.00  42.00   1.00    6.00    --   34.73 -38.00   0.00   76
 17  \w     16.00  52.00   1.00    6.00    --   34.73 -38.00  60.00   36
 18  \w     91.00 171.00   1.00   30.00    --  105.25  61.00 -30.00   80
 19  \w     55.00  82.00   1.00   30.00    --  105.25 -45.00-120.00   27
 20  \w     83.00 111.00   1.00   30.00    --  105.25 -61.00-120.00   28
 21  \w     59.00  85.00   1.00   30.00    --  105.25 178.00 150.00   26
 22  \w     98.00 123.00   1.00   30.00    --  105.25 -45.00-120.00   25
 23  \w     44.00 112.00   1.00   30.00    --  105.25-111.00 -60.00   68
 24  \w     42.00  68.00   1.00   30.00    --  105.25 -94.00-180.00   26
 25  \w     51.00 108.00   1.00   30.00    --  105.25 -94.00  90.00   57
 26  \w    138.00 164.00   1.00   30.00    --  105.25  30.00 -60.00   26
 27  \w     86.00 112.00   1.00   30.00    --  105.25  30.00 -60.00   26
 28  \w     37.00 112.00   1.00   30.00    --  105.25 -45.00 -30.00   75
 29  \w     82.00 107.00   1.00   30.00    --  105.25 -94.00-180.00   25
 30  \w     66.00 127.00   1.00   30.00    --  105.25 -30.00 120.00   61
 31  \w     39.00 132.00   1.00   30.00    --  105.25 -77.00 120.00   93
 32  \w    116.00 142.00   1.00   30.00    --  105.25 178.00 150.00   26
 33  \w     59.00 116.00   1.00   30.00    --  105.25-111.00  30.00   57
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1268274000
_diffrn_orient_matrix_UB_12      -0.0111867000
_diffrn_orient_matrix_UB_13      0.0492386000
_diffrn_orient_matrix_UB_21      0.0116821000
_diffrn_orient_matrix_UB_22      0.0576669000
_diffrn_orient_matrix_UB_23      0.0648108000
_diffrn_orient_matrix_UB_31      -0.0164618000
_diffrn_orient_matrix_UB_32      -0.0448271000
_diffrn_orient_matrix_UB_33      0.0710902000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.1325
_diffrn_reflns_av_unetI/netI     0.1656
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            27391
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        66.597
_diffrn_reflns_theta_max         66.597
_diffrn_reflns_theta_min         3.688
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.552
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.33807
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            green
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.180
_exptl_crystal_description       needle
_exptl_crystal_F_000             1472
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.253
_refine_diff_density_min         -0.313
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.778
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     498
_refine_ls_number_reflns         6939
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.778
_refine_ls_R_factor_all          0.1272
_refine_ls_R_factor_gt           0.0543
_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^)+(0.0440P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1082
_refine_ls_wR_factor_ref         0.1332
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3043
_reflns_number_total             6939
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc07199a2.cif
_cod_data_source_block           exp_3517_sq
_cod_depositor_comments
'Adding full bibliography for 1573430--1573435.cif.'
_cod_original_cell_volume        3932.9(11)
_cod_database_code               1573431
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         'C100 H100 N2 O1'
_shelx_estimated_absorpt_t_max   0.973
_shelx_estimated_absorpt_t_min   0.947
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.49
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1A), C2(H2), C3(H3), C4(H4), C9(H9), C10(H10), C11(H11), C12(H12),
 C14(H14), C16(H16), C17(H17), C22(H22), C23(H23), C27(H27), C28(H28), C33(H33),
  C35(H35), C41(H41), C43(H43)
2.b Idealised Me refined as rotating group:
 C37(H37A,H37B,H37C), C38(H38B,H38A,H38C), C39(H39A,H39B,H39C), C46(H46A,H46B,
 H46C), C47(H47A,H47B,H47C), C48(H48A,H48B,H48C)
2.c Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_shelx_res_checksum              98681
_shelx_fab_checksum              95357
_platon_squeeze_void_probe_radius 1.20
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.043
_oxdiff_exptl_absorpt_empirical_full_min 0.420