Synthesis, structure, and reactivity of fully aryl-substituted pyrroles: toward the synthesis of nitrogen-doped buckybowls.
Yang, Sha; Zhou, Jie; Gan, Ziyang; Wu, Shuai; Shi, Dan; Yan, Hong; Xie, Lili; Cheng, Jiajia; Li, Yuanming; Organic & biomolecular chemistry 23 (2025) 822–826; doi:10.1039/d4ob01835d

data_7160294
_publ_section_title
;
 Synthesis, structure, and reactivity of fully aryl-substituted pyrroles:
 toward the synthesis of nitrogen-doped buckybowls.
;
_journal_issue                   4
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              822
_journal_page_last               826
_journal_paper_doi               10.1039/d4ob01835d
_journal_volume                  23
_journal_year                    2025
_chemical_formula_moiety         'C31 H20 O5'
_chemical_formula_sum            'C31 H20 O5'
_chemical_formula_weight         472.47
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2024-01-30
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2024-03-16 deposited with the CCDC.	2024-12-06 downloaded from the CCDC.
;
_cell_angle_alpha                80.397(2)
_cell_angle_beta                 74.367(3)
_cell_angle_gamma                82.730(3)
_cell_formula_units_Z            4
_cell_length_a                   10.1607(4)
_cell_length_b                   13.9705(4)
_cell_length_c                   17.2919(5)
_cell_measurement_reflns_used    6673
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      55.0340
_cell_measurement_theta_min      2.3850
_cell_volume                     2322.04(14)
_computing_cell_refinement       'CrysAlisPro 1.171.42.84a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.84a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.84a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.973
_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    -72.00  -5.00   0.50    1.00    --   -0.78 -46.00  13.00  134
  2  \w      0.00  25.00   0.50    1.00    --   -0.78 -46.00  13.00   50
  3  \w     -7.00  72.00   0.50    2.00    --   68.44 -46.00  13.00  158
  4  \w     49.00 143.00   0.50    2.00    --   68.44  46.00 163.00  188
  5  \w   -146.00 -46.00   0.50    2.00    --  -70.00 -46.00  13.00  200
  6  \w    -44.00   3.00   0.50    2.00    --  -70.00  46.00 163.00   94
  7  \w      7.00  37.00   0.50    1.00    --   -0.78 -99.00-120.00   60
  8  \w    -25.00  23.00   0.50    1.00    --   -0.78  46.00 163.00   96
  9  \w     31.00  70.00   0.50    1.00    --   -0.78  46.00 163.00   78
 10  \w     89.00 114.00   0.50    2.00    --   68.44  77.00 120.00   50
 11  \w     43.00  92.00   0.50    2.00    --   68.44 -57.00-150.00   98
 12  \w     68.00  93.00   0.50    2.00    --   68.44-125.00  60.00   50
 13  \w     20.00 105.00   0.50    2.00    --   68.44-125.00  30.00  170
 14  \w     56.00 102.00   0.50    2.00    --   68.44-125.00  90.00   92
 15  \w     -9.00  65.00   0.50    2.00    --   68.44 -38.00  30.00  148
 16  \w     -5.00  20.00   0.50    2.00    --   68.44 -57.00-150.00   50
 17  \w     40.00  69.00   0.50    2.00    --   68.44  77.00 120.00   58
 18  \w     91.00 141.00   0.50    2.00    --   68.44 125.00  90.00  100
 19  \w     20.00 108.00   0.50    2.00    --   68.44-125.00 -90.00  176
 20  \w    -93.00 -61.00   0.50    2.00    --  -70.00  77.00-150.00   64
 21  \w    -95.00 -27.00   0.50    2.00    --  -70.00 125.00 150.00  136
 22  \w   -142.00 -90.00   0.50    2.00    --  -70.00 -99.00 120.00  104
 23  \w   -139.00 -86.00   0.50    2.00    --  -70.00-125.00 150.00  106
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1290204000
_diffrn_orient_matrix_UB_12      -0.0363867000
_diffrn_orient_matrix_UB_13      -0.0016923000
_diffrn_orient_matrix_UB_21      0.0465513000
_diffrn_orient_matrix_UB_22      0.0822833000
_diffrn_orient_matrix_UB_23      -0.0451235000
_diffrn_orient_matrix_UB_31      -0.0076155000
_diffrn_orient_matrix_UB_32      0.0377854000
_diffrn_orient_matrix_UB_33      0.0674975000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Ga K\a'
_diffrn_radiation_wavelength     1.3405
_diffrn_reflns_av_R_equivalents  0.0571
_diffrn_reflns_av_unetI/netI     0.0690
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            23602
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        53.543
_diffrn_reflns_theta_max         55.919
_diffrn_reflns_theta_min         2.329
_diffrn_source                   'micro-focus metaljet'
_exptl_absorpt_coefficient_mu    0.474
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77380
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.84a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.351
_exptl_crystal_description       plate
_exptl_crystal_F_000             984
_exptl_crystal_size_max          0.04
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.350
_refine_diff_density_min         -0.225
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.103
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     653
_refine_ls_number_reflns         8938
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.103
_refine_ls_R_factor_all          0.1022
_refine_ls_R_factor_gt           0.0669
_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^)+(0.0689P)^2^+0.7958P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1457
_refine_ls_wR_factor_ref         0.1582
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6514
_reflns_number_total             8938
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ob01835d2.cif
_cod_data_source_block           5
_cod_depositor_comments
'Adding full bibliography for 7160293--7160294.cif.'
_cod_database_code               7160294
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_max   0.995
_shelx_estimated_absorpt_t_min   0.981
_reflns_odcompleteness_completeness 99.47
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     53.78
_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
2.a Aromatic/amide H refined with riding coordinates:
 C26(H26), C9(H9), C40(H40), C10(H10), C11(H11), C3(H3), C2(H2), C30(H30),
 C4(H4), C25(H25), C61(H61), C34(H34), C62(H62), C45(H45), C38(H38), C69(H69),
 C39(H39), C47(H47), C70(H70), C66(H66), C46(H46), C58(H58), C22(H22), C33(H33),
  C59(H59), C31(H31), C23(H23), C67(H67)
2.b Idealised Me refined as rotating group:
 C72(H72A,H72B,H72C), C64(H64A,H64B,H64C), C36(H36A,H36B,H36C), C28(H28A,H28B,
 H28C)
;
_shelx_res_checksum              13964
_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 3.900
_oxdiff_exptl_absorpt_empirical_full_min 0.257