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_1573430
_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 H40 N2, C2 H3 N'
_chemical_formula_sum            'C51 H43 N3'
_chemical_formula_weight         697.88
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2024-04-15
_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                 96.378(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.0996(5)
_cell_length_b                   10.9016(5)
_cell_length_c                   29.2496(12)
_cell_measurement_reflns_used    3142
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      71.4870
_cell_measurement_theta_min      4.1110
_cell_volume                     3834.3(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 (Sheldrick, 2015)'
_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     24.00  92.00   1.00    5.00    --   34.48  57.00   0.00   68
  2  \w    103.00 129.00   1.00   20.00    --  105.88 111.00  30.00   26
  3  \w     75.00 149.00   1.00   20.00    --  105.88 178.00  60.00   74
  4  \w     68.00 172.00   1.00   20.00    --  105.88  15.00-150.00  104
  5  \w     57.00 104.00   1.00   20.00    --  105.88-111.00  30.00   47
  6  \w     45.00 132.00   1.00   20.00    --  105.88 -77.00  30.00   87
  7  \w     37.00  64.00   1.00    5.00    --   34.48 -99.00 150.00   27
  8  \w      1.00  59.00   1.00    5.00    --   34.48 -99.00  60.00   58
  9  \w     27.00  84.00   1.00    5.00    --   34.48-125.00 -60.00   57
 10  \w      9.00 103.00   1.00    5.00    --   34.48  19.00-120.00   94
 11  \w     39.00 129.00   1.00   20.00    --  105.88 -15.00-180.00   90
 12  \w     37.00 109.00   1.00   20.00    --  105.88 -94.00-180.00   72
;
_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      0.0250824000
_diffrn_orient_matrix_UB_12      0.0827052000
_diffrn_orient_matrix_UB_13      0.0425954000
_diffrn_orient_matrix_UB_21      0.0185088000
_diffrn_orient_matrix_UB_22      0.1097523000
_diffrn_orient_matrix_UB_23      -0.0314514000
_diffrn_orient_matrix_UB_31      -0.1242642000
_diffrn_orient_matrix_UB_32      0.0329847000
_diffrn_orient_matrix_UB_33      -0.0021473000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0534
_diffrn_reflns_av_unetI/netI     0.0884
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            13633
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        66.597
_diffrn_reflns_theta_max         66.597
_diffrn_reflns_theta_min         3.040
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.535
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70836
_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    1.209
_exptl_crystal_description       block
_exptl_crystal_F_000             1480
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.266
_refine_diff_density_min         -0.458
_refine_diff_density_rms         0.048
_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     494
_refine_ls_number_reflns         6772
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0889
_refine_ls_R_factor_gt           0.0575
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0454P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1249
_refine_ls_wR_factor_ref         0.1414
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4736
_reflns_number_total             6772
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc07199a2.cif
_cod_data_source_block           exp_3719
_cod_depositor_comments
'Adding full bibliography for 1573430--1573435.cif.'
_cod_database_code               1573430
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         'C100 H10 N5'
_shelx_estimated_absorpt_t_max   0.948
_shelx_estimated_absorpt_t_min   0.856
_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, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N2(H2), C48(H48), C43(H43), C4(H4), C3(H3), C29(H29), C12(H12), C16(H16),
 C31(H31), C45(H45), C15(H15), C41(H41), C38(H38), C47(H47), C46(H46), C39(H39),
  C20(H20), C40(H40), C22(H22), C8(H8), C10(H10), C9(H9)
2.b Idealised Me refined as rotating group:
 C35(H35A,H35B,H35C), C34(H34A,H34B,H34C), C25(H25A,H25B,H25C), C24(H24A,H24B,
 H24C), C33(H33A,H33B,H33C), C26(H26A,H26B,H26C), C51(H51A,H51B,H51C)
;
_shelx_res_checksum              22556
_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 1.480
_oxdiff_exptl_absorpt_empirical_full_min 0.670