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_7160293
_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         'C39 H29 N O5'
_chemical_formula_sum            'C39 H29 N O5'
_chemical_formula_weight         591.669
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_Int_Tables_number      2
_atom_sites_solution_primary     dual
_audit_creation_date             2023-04-24
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2023-12-16 deposited with the CCDC.	2024-12-06 downloaded from the CCDC.
;
_cell_angle_alpha                109.969(8)
_cell_angle_beta                 95.072(8)
_cell_angle_gamma                93.817(8)
_cell_formula_units_Z            2
_cell_length_a                   7.4039(8)
_cell_length_b                   13.9229(12)
_cell_length_c                   16.6050(14)
_cell_measurement_reflns_used    3083
_cell_measurement_temperature    293
_cell_measurement_theta_max      22.7810
_cell_measurement_theta_min      2.3540
_cell_volume                     1593.9(3)
_computing_cell_refinement       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.3 (Bourhis et al., 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.9993
_diffrn_measured_fraction_theta_max 0.9993
_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     -9.00  78.00   0.50    3.00    --  -10.90  55.00-180.00  174
  2  \w    -81.00 -55.00   0.50    3.00    --  -10.90  55.00  60.00   52
  3  \w    -27.00  77.00   0.50    3.00    --  -10.90  55.00  60.00  208
  4  \w    -29.00  79.00   0.50    3.00    --  -10.90  55.00 -60.00  216
  5  \w    -86.00 -60.00   0.50    3.00    --  -10.90  43.00  90.00   52
  6  \w    -48.00  60.00   0.50    3.00    --  -10.90  43.00  90.00  216
  7  \w     -8.00  76.00   0.50    3.00    --  -10.90  29.00 -60.00  168
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC11 (RCD3): quarter-chi single'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0230622000
_diffrn_orient_matrix_UB_12      0.0512942000
_diffrn_orient_matrix_UB_13      0.0141348000
_diffrn_orient_matrix_UB_21      0.0325330000
_diffrn_orient_matrix_UB_22      0.0059381000
_diffrn_orient_matrix_UB_23      0.0430821000
_diffrn_orient_matrix_UB_31      0.0880890000
_diffrn_orient_matrix_UB_32      0.0174189000
_diffrn_orient_matrix_UB_33      -0.0062562000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0743
_diffrn_reflns_av_unetI/netI     0.1077
_diffrn_reflns_Laue_measured_fraction_full 0.9993
_diffrn_reflns_Laue_measured_fraction_max 0.9993
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            21016
_diffrn_reflns_point_group_measured_fraction_full 0.9993
_diffrn_reflns_point_group_measured_fraction_max 0.9993
_diffrn_reflns_theta_full        25.0267
_diffrn_reflns_theta_max         25.03
_diffrn_reflns_theta_min         2.37
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  0.999
_exptl_absorpt_correction_T_min  0.998
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.28b (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear reddish red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   reddish
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.233
_exptl_crystal_description       block
_exptl_crystal_F_000             620.316
_exptl_crystal_size_max          0.02
_exptl_crystal_size_mid          0.01
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.4822
_refine_diff_density_min         -0.3678
_refine_diff_density_rms         0.0947
_refine_ls_d_res_high            0.8400
_refine_ls_d_res_low             8.5962
_refine_ls_goodness_of_fit_ref   1.0203
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    50
_refine_ls_number_parameters     410
_refine_ls_number_reflns         5625
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0203
_refine_ls_R_factor_all          0.1243
_refine_ls_R_factor_gt           0.0722
_refine_ls_shift/su_max          0.0004
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1311P)^2^+0.1656P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1959
_refine_ls_wR_factor_ref         0.2311
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              8
_reflns_limit_h_min              -8
_reflns_limit_k_max              15
_reflns_limit_k_min              -16
_reflns_limit_l_max              19
_reflns_limit_l_min              0
_reflns_number_gt                3237
_reflns_number_total             5625
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d4ob01835d2.cif
_cod_data_source_block           4c
_cod_depositor_comments
'Adding full bibliography for 7160293--7160294.cif.'
_cod_database_code               7160293
_reflns_odcompleteness_completeness 99.91
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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:
 C00G(H00G), C00I(H00I), C00M(H00M), C00R(H00R), C00S(H00S), C00T(H00T),
 C00U(H00U), C00V(H00V), C00X(H00X), C00Z(H00Z), C010(H010), C011(H011),
 C012(H012), C013(H013), C017(H017), C018(H018), C019(H019)
2.b Idealised Me refined as rotating group:
 C015(H01a,H01b,H01c), C016(H01d,H01e,H01f), C01A(H01g,H01h,H01i), C01B(H01j,
 H01k,H01l)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_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 1.259
_oxdiff_exptl_absorpt_empirical_full_min 0.786