Divergent transformation of <i>C</i>,<i>N</i>-cyclic-<i>N</i>'-acyl azomethine imines by reaction with diazo compounds.
Ohno, Haruki; Takahashi, Ryosuke; Suga, Takuya; Soeta, Takahiro; Ukaji, Yutaka; Organic & biomolecular chemistry 21 (2023) 7891–7894; doi:10.1039/d3ob01165h

data_7159559
_publ_section_title
;
 Divergent transformation of <i>C</i>,<i>N</i>-cyclic-<i>N</i>'-acyl
 azomethine imines by reaction with diazo compounds.
;
_journal_issue                   39
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              7891
_journal_page_last               7894
_journal_paper_doi               10.1039/d3ob01165h
_journal_volume                  21
_journal_year                    2023
_chemical_formula_moiety         'C20 H20 N2 O3'
_chemical_formula_sum            'C20 H20 N2 O3'
_chemical_formula_weight         336.393
_chemical_name_systematic        'Ukaji 6'
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_symmetry_Int_Tables_number      61
_atom_sites_solution_primary     iterative
_audit_creation_date             2021-09-18
_audit_creation_method
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_audit_update_record
;
2021-12-16 deposited with the CCDC.	2023-08-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   9.8436(4)
_cell_length_b                   18.8060(7)
_cell_length_c                   18.8060(7)
_cell_measurement_reflns_used    9941
_cell_measurement_temperature    273.15
_cell_measurement_theta_max      72.50
_cell_measurement_theta_min      4.70
_cell_volume                     3481.3(2)
_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  'olex2.refine 1.3 (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve 1.3 (Bourhis et al., 2015)'
_diffrn_ambient_temperature      273.15
_diffrn_measured_fraction_theta_full 0.9981
_diffrn_measured_fraction_theta_max 0.9930
_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  0.0341
_diffrn_reflns_av_unetI/netI     0.0214
_diffrn_reflns_Laue_measured_fraction_full 0.9981
_diffrn_reflns_Laue_measured_fraction_max 0.9930
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            27009
_diffrn_reflns_point_group_measured_fraction_full 0.9981
_diffrn_reflns_point_group_measured_fraction_max 0.9930
_diffrn_reflns_theta_full        67.6786
_diffrn_reflns_theta_max         72.49
_diffrn_reflns_theta_min         4.70
_diffrn_source_current           50.0
_diffrn_source_power             2.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.705
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.6259
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016) was used for absorption correction.
wR2(int) was 0.1253 before and 0.0436 after correction.
The Ratio of minimum to maximum transmission is 0.8305.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.284
_exptl_crystal_description       needle
_exptl_crystal_F_000             1428.615
_exptl_crystal_size_max          1.3
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.1820
_refine_diff_density_min         -0.2501
_refine_diff_density_rms         0.0423
_refine_ls_d_res_high            0.8083
_refine_ls_d_res_low             9.4030
_refine_ls_goodness_of_fit_ref   1.0380
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    35
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3421
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0380
_refine_ls_R_factor_all          0.0369
_refine_ls_R_factor_gt           0.0347
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0399P)^2^+1.4007P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0853
_refine_ls_wR_factor_ref         0.0871
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              11
_reflns_limit_h_min              0
_reflns_limit_k_max              23
_reflns_limit_k_min              0
_reflns_limit_l_max              23
_reflns_limit_l_min              0
_reflns_number_gt                3203
_reflns_number_total             3421
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d3ob01165h2.cif
_cod_data_source_block           210917_sakurai_0ma
_cod_depositor_comments
'Adding full bibliography for 7159559--7159560.cif.'
_cod_database_code               7159559
_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.a Secondary CH2 refined with riding coordinates:
 C11(H11a,H11b), C13(H13a,H13b), C15(H15a,H15b)
2.b Aromatic/amide H refined with riding coordinates:
 C12(H12), C10(H10), C14(H14), C4(H4), C17(H17), C1a(H1a), C18(H18), C16(H16),
 C8(H8), C7(H7), N1(H1)
2.c Idealised Me refined as rotating group:
 C19(H19a,H19b,H19c)
;
_olex2_submission_special_instructions 'No special instructions were received'