“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_7063142
_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         'C22 H26 N4 O2'
_chemical_formula_sum            'C22 H26 N4 O2'
_chemical_formula_weight         378.47
_chemical_name_systematic        WF-2
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-02-09
_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                90
_cell_angle_beta                 106.99(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   29.852(15)
_cell_length_b                   8.3792(16)
_cell_length_c                   16.947(4)
_cell_measurement_reflns_used    174
_cell_measurement_temperature    150.0
_cell_measurement_theta_max      43.12
_cell_measurement_theta_min      6.34
_cell_volume                     4054(2)
_computing_cell_refinement       'SAINT V8.40C (?, 2016)'
_computing_data_reduction        'SAINT V8.40C (?, 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 0.973
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.1291
_diffrn_reflns_av_unetI/netI     0.1236
_diffrn_reflns_Laue_measured_fraction_full 0.973
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            11024
_diffrn_reflns_point_group_measured_fraction_full 0.973
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        63.870
_diffrn_reflns_theta_max         63.870
_diffrn_reflns_theta_min         3.096
_diffrn_source_current           1.1
_diffrn_source_power             0.055
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.650
_exptl_absorpt_correction_T_max  0.7524
_exptl_absorpt_correction_T_min  0.4280
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'clear yellowish colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.240
_exptl_crystal_description       needle
_exptl_crystal_F_000             1616
_exptl_crystal_preparation       'THF ANN nhexane'
_exptl_crystal_recrystallization_method 'nhexane to THF'
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.561
_refine_diff_density_min         -0.397
_refine_diff_density_rms         0.117
_refine_ls_extinction_coef       0.0028(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     258
_refine_ls_number_reflns         3265
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.2199
_refine_ls_R_factor_gt           0.1445
_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^)+(0.2800P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3864
_refine_ls_wR_factor_ref         0.4465
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1537
_reflns_number_total             3265
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4nj00933a2.cif
_cod_data_source_block           cu_20211202_wf_2_0m
_cod_depositor_comments
'Adding full bibliography for 7063139--7063144.cif.'
_cod_database_code               7063142
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.994
_shelx_estimated_absorpt_t_min   0.938
_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
2. Restrained distances
 C4-C3
 1.51 with sigma of 0.02
3.a Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C19(H19A,H19B), C16(H16A,H16B), C7(H7A,H7B)
3.b Aromatic/amide H refined with riding coordinates:
 N4(H4), N1(H1), C12(H12), C1(H1A), C22(H22), C11(H11)
3.c Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C), C20(H20A,H20B,H20C), C17(H17A,H17B,H17C), C8(H8A,H8B,H8C)
;
_olex2_submission_original_sample_id WF-2
_olex2_submission_special_instructions 'No special instructions were received'