Stabilizing 4π electron pyrrolyl cations by inducing aromaticity.
Gupta, Astha; Dar, Mohammad Ovais; Singh, Tejender; Dubey, Gurudutt; Sahoo, Subash C.; Bharatam, Prasad V.; Chemical communications (Cambridge, England) 61 (2024) 105–108; doi:10.1039/d4cc04560b

data_7134017
_publ_section_title
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 Stabilizing 4&#x3c0; electron pyrrolyl cations by inducing aromaticity.
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_journal_issue                   1
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              105
_journal_page_last               108
_journal_paper_doi               10.1039/d4cc04560b
_journal_volume                  61
_journal_year                    2024
_chemical_formula_moiety
'C32 H26 N5, 0.3(C O4 S), 0.7(O4 S), 3(O), 0.7(C)'
_chemical_formula_sum            'C33 H26 N5 O7 S'
_chemical_formula_weight         636.65
_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     iterative
_audit_creation_date             2024-11-07
_audit_creation_method
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Olex2 1.5-ac6-016
(compiled 2024.01.13 svn.r2f8d729c for Rigaku Oxford Diffraction, GUI svn.r6897)
;
_audit_update_record
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2024-11-10 deposited with the CCDC.	2024-11-18 downloaded from the CCDC.
;
_cell_angle_alpha                72.121(4)
_cell_angle_beta                 65.597(4)
_cell_angle_gamma                88.754(3)
_cell_formula_units_Z            2
_cell_length_a                   11.0277(5)
_cell_length_b                   12.5158(4)
_cell_length_c                   13.0402(5)
_cell_measurement_reflns_used    20528
_cell_measurement_temperature    222(2)
_cell_measurement_theta_max      21.3690
_cell_measurement_theta_min      3.2920
_cell_volume                     1548.36(13)
_computing_molecular_graphics    'Olex2 1.5-ac6-016 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac6-016 (Dolomanov et al., 2009)'
_computing_structure_refinement
'olex2.refine 1.5-ac6-016 (Bourhis et al., 2015)'
_computing_structure_solution
'olex2.solve 1.5-ac6-016 (Bourhis et al., 2015)'
_diffrn_ambient_temperature      222.15
_diffrn_measured_fraction_theta_full 0.9970
_diffrn_measured_fraction_theta_max 0.9469
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0513
_diffrn_reflns_av_unetI/netI     0.0600
_diffrn_reflns_Laue_measured_fraction_full 0.9970
_diffrn_reflns_Laue_measured_fraction_max 0.9469
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            24433
_diffrn_reflns_point_group_measured_fraction_full 0.9970
_diffrn_reflns_point_group_measured_fraction_max 0.9469
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         27.09
_diffrn_reflns_theta_min         3.26
_exptl_absorpt_coefficient_mu    0.162
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.366
_exptl_crystal_description       block
_exptl_crystal_F_000             662.704
_exptl_crystal_size_max          0.02
_exptl_crystal_size_mid          0.012
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.9455
_refine_diff_density_min         -1.1100
_refine_diff_density_rms         0.1082
_refine_ls_d_res_high            0.7805
_refine_ls_d_res_low             6.2446
_refine_ls_goodness_of_fit_ref   1.2458
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    54
_refine_ls_number_parameters     435
_refine_ls_number_reflns         6459
_refine_ls_number_restraints     66
_refine_ls_restrained_S_all      1.2390
_refine_ls_R_factor_all          0.1414
_refine_ls_R_factor_gt           0.1043
_refine_ls_shift/su_max          -0.0008
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.2P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3178
_refine_ls_wR_factor_ref         0.3471
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              14
_reflns_limit_h_min              -12
_reflns_limit_k_max              15
_reflns_limit_k_min              -15
_reflns_limit_l_max              16
_reflns_limit_l_min              0
_reflns_number_gt                4074
_reflns_number_total             6459
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d4cc04560b2.cif
_cod_data_source_block           ex-nipphe_autored
_cod_depositor_comments          'Adding full bibliography for 7134017.cif.'
_cod_database_code               7134017
_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. Uiso/Uaniso restraints and constraints
Uanis(C33B) \\sim Ueq: with sigma of 0.5 and sigma for terminal atoms of 1
Uanis(C33B) = Uanis(C33A)
Uanis(S1A) = Uanis(S1B)
Uanis(O2A) = Uanis(O2B)
Uanis(O1A) = Uanis(O1B)
Uanis(O3A) = Uanis(O3B)
Uanis(O4A) = Uanis(O4B)
Uanis(C33A) = Uanis(C33B)
3. Rigid body (RIGU) restrains
 S1A, O1A, O2A, C33A, O3A, O4A
 with sigma for 1-2 distances of 0.003 and sigma for 1-3 distances of 0.003
 S1B, O4B, O2B, C33B, O3B, O1B
 with sigma for 1-2 distances of 0.003 and sigma for 1-3 distances of 0.003
4. Others
 Fixed Sof: S1A(0.7) O2A(0.7) O1A(0.7) O3A(0.7) C33A(0.7) O4A(0.7) S1B(0.3)
 O2B(0.3) O1B(0.3) O3B(0.3) C33B(0.3) O4B(0.3)
5.a Aromatic/amide H refined with riding coordinates:
 C16(H16), C9(H9), C6(H6), C17(H17), C27(H27), C30(H30), C13(H13), C5(H5),
 C25(H25), C3(H3), C28(H28), C4(H4), C29(H29), C10(H10), C11(H11), C24(H24),
 C12(H12), C23(H23), C21(H21), C22(H22)
5.b Idealised Me refined as rotating group:
 C32(H32a,H32b,H32c), C1(H1a,H1b,H1c)
;
_olex2_submission_special_instructions 'No special instructions were received'