“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_7063144
_publ_section_title
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 &#x201C;One-pot&#x201D; synthesis of oligopyrrolic dialdehydes
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_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         'C18 H23 N2 O2, C18 H24 N2 O2'
_chemical_formula_sum            'C36 H47 N4 O4'
_chemical_formula_weight         599.80
_chemical_name_systematic        WF-X
_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
_audit_creation_date             2022-02-28
_audit_creation_method
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Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
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_audit_update_record
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2023-10-03 deposited with the CCDC.	2024-04-08 downloaded from the CCDC.
;
_cell_angle_alpha                72.2350(10)
_cell_angle_beta                 66.4510(10)
_cell_angle_gamma                65.2320(10)
_cell_formula_units_Z            2
_cell_length_a                   12.2720(2)
_cell_length_b                   12.5331(2)
_cell_length_c                   13.7088(2)
_cell_measurement_reflns_used    7569
_cell_measurement_temperature    173.0
_cell_measurement_theta_max      63.51
_cell_measurement_theta_min      3.94
_cell_volume                     1730.90(5)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      173.0
_diffrn_measured_fraction_theta_full 0.9981
_diffrn_measured_fraction_theta_max 0.9981
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0577
_diffrn_reflns_av_unetI/netI     0.0358
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            27340
_diffrn_reflns_theta_full        63.8129
_diffrn_reflns_theta_max         63.81
_diffrn_reflns_theta_min         3.57
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.598
_exptl_absorpt_correction_T_max  0.7524
_exptl_absorpt_correction_T_min  0.6692
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0823 before and 0.0592 after correction.
The Ratio of minimum to maximum transmission is 0.8894.
The \l/2 correction factor is Not present.
;
_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    1.1507
_exptl_crystal_description       block
_exptl_crystal_F_000             647.9531
_exptl_crystal_preparation       'CHCl3/Isopropyl Ether'
_exptl_crystal_recrystallization_method 'CHCl3/Isopropyl Ether'
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.4
_refine_diff_density_max         0.4248
_refine_diff_density_min         -0.5299
_refine_diff_density_rms         0.0615
_refine_ls_d_res_high            0.8591
_refine_ls_d_res_low             12.3939
_refine_ls_goodness_of_fit_ref   1.0440
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    88
_refine_ls_number_parameters     437
_refine_ls_number_reflns         5708
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.0434
_refine_ls_R_factor_all          0.0982
_refine_ls_R_factor_gt           0.0677
_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^)+(0.0794P)^2^+1.5251P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1690
_refine_ls_wR_factor_ref         0.1945
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              14
_reflns_limit_h_min              -12
_reflns_limit_k_max              14
_reflns_limit_k_min              -13
_reflns_limit_l_max              15
_reflns_limit_l_min              0
_reflns_number_gt                3900
_reflns_number_total             5708
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d4nj00933a2.cif
_cod_data_source_block           t
_cod_depositor_comments
'Adding full bibliography for 7063139--7063144.cif.'
_cod_database_code               7063144
_olex2_refinement_description
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1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C5B-C4B
 1.5 with sigma of 0.01
 C22-C23A
 1.52 with sigma of 0.01
 C4B-C3 \\sim C7-C6
 with sigma of 0.02
 C22-C23A \\sim C23B-C22
 with sigma of 0.02
3. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.0001 and sigma for 1-3 distances of 0.0002
4. Others
 Sof(H22)=Sof(C23A)=Sof(H23d)=Sof(H23e)=Sof(H23f)=Sof(H22c)=Sof(H22d)=1-FVAR(1)
 Sof(H22)=Sof(C23B)=Sof(H23a)=Sof(H23b)=Sof(H23c)=Sof(H22a)=Sof(H22b)=FVAR(1)
 Sof(C4A)=Sof(H4Aa)=Sof(H4Ab)=1-FVAR(2)
 Sof(C4B)=Sof(H4Ba)=Sof(H4Bb)=FVAR(2)
 Sof(C5A)=Sof(H5Aa)=Sof(H5Ab)=Sof(H5Ac)=1-FVAR(3)
 Sof(C5B)=Sof(H5Ba)=Sof(H5Bb)=Sof(H5Bc)=FVAR(3)
5.a Secondary CH2 refined with riding coordinates:
 C25(H25a,H25b), C30(H30a,H30b), C33(H33a,H33b), C7(H7a,H7b), C15(H15a,H15b),
 C4B(H4Ba,H4Bb), C4A(H4Aa,H4Ab), C22(H22a,H22b), C22(H22c,H22d)
5.b Aromatic/amide H refined with riding coordinates:
 N4(H4), N2(H2), N1(H1), N3(H3), C36(H36), C18(H18), C1(H1a), C12(H12), C19(H19)
5.c Idealised Me refined as rotating group:
 C8(H8a,H8b,H8c), C31(H31a,H31b,H31c), C34(H34a,H34b,H34c), C26(H26a,H26b,
 H26c), C23B(H23a,H23b,H23c), C16(H16a,H16b,H16c), C5B(H5Ba,H5Bb,H5Bc),
 C13(H13a,H13b,H13c), C23A(H23d,H23e,H23f), C5A(H5Aa,H5Ab,H5Ac)
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_olex2_submission_special_instructions 'No special instructions were received'