“One-pot” synthesis of oligopyrrolic dialdehydes
Wang, Fei; Zhang, Yi; Zhou, Wei; Long, Zhiqing; Xiong, Shenglun; Zhang, Qinpeng; Sessler, Jonathan L.; He, Qing; New Journal of Chemistry 48 (2024) 8153–8157; doi:10.1039/D4NJ00933A

data_7063141
_publ_section_title
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 &#x201C;One-pot&#x201D; synthesis of oligopyrrolic dialdehydes
;
_journal_issue                   18
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              8153
_journal_page_last               8157
_journal_paper_doi               10.1039/D4NJ00933A
_journal_volume                  48
_journal_year                    2024
_chemical_formula_moiety         'H2 O, C22 H26 N4 O2'
_chemical_formula_sum            'C22 H28 N4 O3'
_chemical_formula_weight         396.48
_chemical_name_systematic        WF-3
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2022-02-10
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2023-10-03 deposited with the CCDC.	2024-04-08 downloaded from the CCDC.
;
_cell_angle_alpha                105.506(6)
_cell_angle_beta                 102.442(6)
_cell_angle_gamma                90.015(6)
_cell_formula_units_Z            2
_cell_length_a                   8.6855(7)
_cell_length_b                   9.1540(9)
_cell_length_c                   13.8725(13)
_cell_measurement_reflns_used    4144
_cell_measurement_temperature    150.0
_cell_measurement_theta_max      72.155
_cell_measurement_theta_min      5.018
_cell_volume                     1035.89(17)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      150.0
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0814
_diffrn_reflns_av_unetI/netI     0.0732
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            5671
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.292
_diffrn_reflns_theta_min         5.023
_exptl_absorpt_coefficient_mu    0.695
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'dull brownish brown'
_exptl_crystal_colour_lustre     dull
_exptl_crystal_colour_modifier   brownish
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.271
_exptl_crystal_description       needle
_exptl_crystal_F_000             424
_exptl_crystal_preparation       CHCl3/n-hexane
_exptl_crystal_recrystallization_method CHCl3/n-hexane
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.04
_refine_diff_density_max         1.089
_refine_diff_density_min         -0.533
_refine_diff_density_rms         0.108
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     269
_refine_ls_number_reflns         3985
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.1331
_refine_ls_R_factor_gt           0.1186
_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^)+(0.1818P)^2^+1.4580P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2934
_refine_ls_wR_factor_ref         0.3077
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3264
_reflns_number_total             3985
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4nj00933a2.cif
_cod_data_source_block           cu_20211202_wf_3_0m_5
_cod_depositor_comments
;
Adding full bibliography for 7063139--7063144.cif.

2025-03-29
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C44 H56 N8 O6'
_cod_original_formula_weight         792.96
_cod_original_formula_moiety         '2(H2 O), 2(C22 H26 N4 O2)'
_cod_original_formula_units_Z            1
_cod_database_code               7063141
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.973
_shelx_estimated_absorpt_t_min   0.934
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H,H) groups
2. Restrained distances
 H3A-H4
 2.52 with sigma of 0.01
 H1-H3B
 2.52 with sigma of 0.01
 H4-H3B
 2.52 with sigma of 0.01
3.a Free rotating group:
 O3(H3A,H3B)
3.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C16(H16A,H16B), C19(H19A,H19B), C7(H7A,H7B)
3.c Aromatic/amide H refined with riding coordinates:
 N4(H4), N1(H1), C1(H1A), C11(H11), C12(H12), C22(H22)
3.d Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C17(H17A,H17B,H17C), C5(H5A,H5B,H5C), C20(H20A,H20B,H20C)
;
_olex2_submission_original_sample_id WF-3
_olex2_submission_special_instructions 'No special instructions were received'