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_1573434
_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 O'
_chemical_formula_sum            'C49 H39 B N2 O'
_chemical_formula_weight         682.63
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2024-04-23
_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                104.186(8)
_cell_angle_beta                 110.328(9)
_cell_angle_gamma                96.071(8)
_cell_formula_units_Z            2
_cell_length_a                   11.9190(12)
_cell_length_b                   12.5825(11)
_cell_length_c                   14.8081(16)
_cell_measurement_reflns_used    1131
_cell_measurement_temperature    99.98(10)
_cell_measurement_theta_max      70.3120
_cell_measurement_theta_min      3.6820
_cell_volume                     1974.0(4)
_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 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.98(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0697
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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     23.00 100.00   1.00    5.00    --   34.73  38.00 -60.00   77
  2  \w     40.00  93.00   1.00    5.00    --   34.73  57.00-150.00   53
  3  \w    104.00 130.00   1.00   25.00    --  105.25 111.00-180.00   26
  4  \w    149.00 174.00   1.00   25.00    --  105.25  45.00-120.00   25
  5  \w     92.00 167.00   1.00   25.00    --  105.25  30.00   0.00   75
  6  \w    131.00 163.00   1.00   25.00    --  105.25 111.00 120.00   32
  7  \w     57.00  84.00   1.00    5.00    --   34.73  57.00 120.00   27
  8  \w     35.00 100.00   1.00    5.00    --   34.73  57.00  30.00   65
  9  \w     38.00 125.00   1.00   25.00    --  105.25 -30.00  60.00   87
 10  \w     82.00 108.00   1.00   25.00    --  105.25 -94.00 150.00   26
 11  \w     41.00 132.00   1.00   25.00    --  105.25 -77.00  90.00   91
 12  \w     79.00 107.00   1.00   25.00    --  105.25 -94.00 -60.00   28
 13  \w     67.00 105.00   1.00   25.00    --  105.25 -94.00-120.00   38
 14  \w     93.00 121.00   1.00   25.00    --  105.25 -61.00-150.00   28
 15  \w     50.00  76.00   1.00    5.00    --   34.73-125.00 -30.00   26
 16  \w      5.00  72.00   1.00    5.00    --   34.73 -99.00 -30.00   67
 17  \w     40.00  80.00   1.00   25.00    --  105.25 -61.00-150.00   40
 18  \w     36.00  62.00   1.00   25.00    --  105.25 -94.00 -60.00   26
 19  \w     34.00 129.00   1.00   25.00    --  105.25 -15.00-180.00   95
 20  \w     79.00 172.00   1.00   25.00    --  105.25  77.00-150.00   93
 21  \w     40.00 112.00   1.00   25.00    --  105.25-111.00  90.00   72
 22  \w     23.00  95.00   1.00    5.00    --   34.73  57.00  90.00   72
 23  \w     57.00 133.00   1.00   25.00    --  105.25 178.00 120.00   76
 24  \w    -34.00  23.00   1.00    5.00    --   34.73 -38.00 120.00   57
 25  \w     40.00  88.00   1.00    5.00    --   34.73-125.00-180.00   48
;
_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      0.1074216000
_diffrn_orient_matrix_UB_12      0.0910364000
_diffrn_orient_matrix_UB_13      0.0146620000
_diffrn_orient_matrix_UB_21      -0.0892547000
_diffrn_orient_matrix_UB_22      0.0502244000
_diffrn_orient_matrix_UB_23      -0.0728311000
_diffrn_orient_matrix_UB_31      -0.0192199000
_diffrn_orient_matrix_UB_32      0.0766414000
_diffrn_orient_matrix_UB_33      0.0895909000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0816
_diffrn_reflns_av_unetI/netI     0.1619
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            12275
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        66.599
_diffrn_reflns_theta_max         66.599
_diffrn_reflns_theta_min         3.339
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.519
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.59263
_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    1.148
_exptl_crystal_description       plate
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.334
_refine_diff_density_min         -0.663
_refine_diff_density_rms         0.080
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     485
_refine_ls_number_reflns         6960
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.1507
_refine_ls_R_factor_gt           0.0818
_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^)+(0.0738P)^2^+0.2096P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1879
_refine_ls_wR_factor_ref         0.2274
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3802
_reflns_number_total             6960
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc07199a2.cif
_cod_data_source_block           exp_3736_sq
_cod_depositor_comments
'Adding full bibliography for 1573430--1573435.cif.'
_cod_database_code               1573434
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.975
_shelx_estimated_absorpt_t_min   0.950
_reflns_odcompleteness_completeness 99.86
_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. Uiso/Uaniso restraints and constraints
Uanis(C01H) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01
3.a Aromatic/amide H refined with riding coordinates:
 C00E(H00E), C00G(H00G), C00N(H00N), C00O(H00O), C00Q(H00Q), C00R(H00R),
 C00S(H00S), C00W(H00W), C00X(H00X), C010(H010), C012(H012), C016(H016),
 C018(H018), C01A(H01G), C01B(H01H), C01C(H01I), C01D(H01J), C01E(H01K),
 C01F(H01L), C01G(H01M)
3.b Idealised Me refined as rotating group:
 C00Y(H00A,H00B,H00C), C017(H01A,H01B,H01C), C019(H01D,H01E,H01F), C01H(H01N,
 H01O,H01P), C01I(H01Q,H01R,H01S), C01J(H01T,H01U,H01V)
3.c Idealised tetrahedral OH refined as rotating group:
 O004(H004)
;
_shelx_res_checksum              53575
_shelx_fab_checksum              93248
_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 2.353
_oxdiff_exptl_absorpt_empirical_full_min 0.620