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_1573435
_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'
_chemical_formula_sum            'C49 H39 B N2'
_chemical_formula_weight         666.63
_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             2023-11-24
_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                103.399(7)
_cell_angle_beta                 109.908(8)
_cell_angle_gamma                94.935(7)
_cell_formula_units_Z            2
_cell_length_a                   11.6677(12)
_cell_length_b                   12.7694(11)
_cell_length_c                   14.5328(8)
_cell_measurement_reflns_used    2183
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      69.5590
_cell_measurement_theta_min      3.3460
_cell_volume                     1948.0(3)
_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      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0697
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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   -102.00 -76.00   1.00    5.00    --  -34.73 -57.00 -30.00   26
  2  \w    -32.00  51.00   1.00    5.00    --   34.73 -38.00  60.00   83
  3  \w    -33.00  37.00   1.00    5.00    --   34.73 -38.00 150.00   70
  4  \w     17.00  44.00   1.00    5.00    --   34.73  38.00-120.00   27
  5  \w     36.00  88.00   1.00    5.00    --   34.73-125.00-180.00   52
  6  \w      8.00  97.00   1.00    5.00    --   34.73  77.00 -90.00   89
  7  \w     23.00 104.00   1.00    5.00    --   34.73  38.00  30.00   81
  8  \w     71.00 104.00   1.00    5.00    --   34.73  38.00-120.00   33
  9  \w     42.00  68.00   1.00    5.00    --   34.73 -99.00 -30.00   26
 10  \w     32.00  70.00   1.00    5.00    --   34.73 -99.00  30.00   38
 11  \w     38.00  80.00   1.00   20.00    --  105.88 -94.00 120.00   42
 12  \w     84.00 116.00   1.00   20.00    --  105.88-111.00 -60.00   32
 13  \w     98.00 172.00   1.00   20.00    --  105.88  61.00-180.00   74
 14  \w     56.00 124.00   1.00   20.00    --  105.88 -77.00-180.00   68
 15  \w     39.00 120.00   1.00   20.00    --  105.88 -45.00 120.00   81
 16  \w     65.00  99.00   1.00   20.00    --  105.88 178.00  90.00   34
 17  \w     42.00 104.00   1.00   20.00    --  105.88 -45.00-120.00   62
 18  \w    120.00 150.00   1.00   20.00    --  105.88 111.00  30.00   30
 19  \w     38.00 121.00   1.00   20.00    --  105.88 -45.00  30.00   83
 20  \w     39.00  66.00   1.00   20.00    --  105.88 -61.00  30.00   27
 21  \w    105.00 133.00   1.00   20.00    --  105.88 178.00  90.00   28
 22  \w     62.00 110.00   1.00   20.00    --  105.88-111.00-180.00   48
 23  \w     37.00 108.00   1.00   20.00    --  105.88 -94.00  30.00   71
 24  \w     40.00 174.00   1.00   20.00    --  105.88   0.00 -30.00  134
;
_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      -0.1192533000
_diffrn_orient_matrix_UB_12      -0.0860683000
_diffrn_orient_matrix_UB_13      -0.0396515000
_diffrn_orient_matrix_UB_21      -0.0162247000
_diffrn_orient_matrix_UB_22      0.0402870000
_diffrn_orient_matrix_UB_23      0.1025068000
_diffrn_orient_matrix_UB_31      -0.0768004000
_diffrn_orient_matrix_UB_32      0.0828689000
_diffrn_orient_matrix_UB_33      -0.0412457000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0516
_diffrn_reflns_av_unetI/netI     0.0802
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            11838
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        66.600
_diffrn_reflns_theta_max         66.600
_diffrn_reflns_theta_min         3.368
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.495
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.76183
_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            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.137
_exptl_crystal_description       needle
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.541
_refine_diff_density_min         -0.265
_refine_diff_density_rms         0.100
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     475
_refine_ls_number_reflns         6887
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.1166
_refine_ls_R_factor_gt           0.0815
_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^)+(0.1341P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2160
_refine_ls_wR_factor_ref         0.2447
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4447
_reflns_number_total             6887
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc07199a2.cif
_cod_data_source_block           exp_3473_sq
_cod_depositor_comments
'Adding full bibliography for 1573430--1573435.cif.'
_cod_database_code               1573435
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         'C100 H100 N1 O1 B1'
_shelx_estimated_absorpt_t_max   0.976
_shelx_estimated_absorpt_t_min   0.976
_reflns_odcompleteness_completeness 99.90
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.49
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, {H26A,H26B,H26C} of C26, {H28A,H28B,H28C} of C28
 At 1.5 times of:
  {H38A,H38B,H38C} of C38, {H39A,H39B,H39C} of C39, {H40A,H40B,H40C} of C40,
  {H47A,H47B,H47C} of C47, {H49A,H49B,H49C} of C49, {H48A,H48B,H48C} of C48
2. Others
 Fixed Sof: H26A(0.5) H26B(0.5) H26C(0.5) H28A(0.5) H28B(0.5) H28C(0.5)
3.a Secondary CH2 refined with riding coordinates:
 C26(H26B,H26C), C28(H28A,H28B)
3.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C6(H6), C7(H7), C8(H8), C9(H9), C11(H11), C13(H13), C14(H14),
 C16(H16), C17(H17), C21(H21), C22(H22), C26(H26A), C27(H27), C28(H28C),
 C34(H34), C36(H36), C42(H42), C44(H44)
3.c Idealised Me refined as rotating group:
 C38(H38A,H38B,H38C), C39(H39A,H39B,H39C), C40(H40A,H40B,H40C), C47(H47A,H47B,
 H47C), C48(H48A,H48B,H48C), C49(H49A,H49B,H49C)
;
_shelx_res_checksum              62116
_shelx_fab_checksum              65403
_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 1.503
_oxdiff_exptl_absorpt_empirical_full_min 0.628