Mild and efficient construction of nitrogen-containing heterocycles from <i>ortho</i>-ethynylbenzaldehydes and anilines.
Zhao, Juan; Qian, Hui-Min; Zi, You; Ji, Shun-Jun; Xu, Xiao-Ping; Organic & biomolecular chemistry 23 (2025) 6938–6942; doi:10.1039/d5ob00634a

data_7160612
_publ_section_title
;
 Mild and efficient construction of nitrogen-containing heterocycles from
 <i>ortho</i>-ethynylbenzaldehydes and anilines.
;
_journal_issue                   29
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              6938
_journal_page_last               6942
_journal_paper_doi               10.1039/d5ob00634a
_journal_volume                  23
_journal_year                    2025
_chemical_formula_moiety         'C21 H18 N2'
_chemical_formula_sum            'C21 H18 N2'
_chemical_formula_weight         298.37
_chemical_melting_point          117.8
_chemical_name_systematic        (E)-3-methyl-N,2-di-p-tolylisoindolin-1-imine
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-04-07
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2025-02-21 deposited with the CCDC.	2025-06-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   14.6041(3)
_cell_length_b                   10.4311(2)
_cell_length_c                   21.7838(4)
_cell_measurement_reflns_used    18303
_cell_measurement_temperature    294.15
_cell_measurement_theta_max      31.5510
_cell_measurement_theta_min      1.9770
_cell_volume                     3318.47(11)
_computing_cell_refinement       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      294.15
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w   -110.00  70.00   0.50    1.00    --  -20.00   0.00   0.00  360
  2  \w    -47.00  70.00   0.50    1.00    --  -20.00  70.00  90.00  234
  3  \w    -47.00  70.00   0.50    1.00    --  -20.00  70.00 180.00  234
  4  \w    -25.00  70.00   0.50    1.00    --  -20.00  70.00   0.00  190
  5  \w   -110.00 -15.00   0.50    1.00    --  -20.00 -70.00   0.00  190
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  'Rigaku mm007 Saturn 944+'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0319530000
_diffrn_orient_matrix_UB_12      -0.0101596000
_diffrn_orient_matrix_UB_13      0.0240327000
_diffrn_orient_matrix_UB_21      0.0356324000
_diffrn_orient_matrix_UB_22      0.0236235000
_diffrn_orient_matrix_UB_23      -0.0190021000
_diffrn_orient_matrix_UB_31      -0.0082331000
_diffrn_orient_matrix_UB_32      0.0629626000
_diffrn_orient_matrix_UB_33      0.0110165000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0679
_diffrn_reflns_av_unetI/netI     0.0213
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            45891
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         2.333
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.070
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.63130
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.194
_exptl_crystal_description       block
_exptl_crystal_F_000             1264
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.140
_refine_diff_density_min         -0.157
_refine_diff_density_rms         0.027
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         3390
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.0598
_refine_ls_R_factor_gt           0.0510
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0564P)^2^+0.6356P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1263
_refine_ls_wR_factor_ref         0.1325
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2930
_reflns_number_total             3390
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob00634a2.cif
_cod_data_source_block           r20230407a_autored
_cod_depositor_comments
'Adding full bibliography for 7160611--7160612.cif.'
_cod_database_code               7160612
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C11 H10 N O'
_shelx_estimated_absorpt_t_max   0.986
_shelx_estimated_absorpt_t_min   0.980
_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.a Ternary CH refined with riding coordinates:
 C008(H008)
2.b Aromatic/amide H refined with riding coordinates:
 C00A(H00A), C00C(H00C), C00D(H00D), C00F(H00G), C00G(H00H), C00H(H00I),
 C00I(H00J), C00J(H00K), C00K(H00L), C00L(H00M), C00M(H00N), C00N(H00O),
 C005(H005), C009(H009)
2.c Idealised Me refined as rotating group:
 C00E(H00B,H00E,H00F)
;
_shelx_res_checksum              28366
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.491
_oxdiff_exptl_absorpt_empirical_full_min 0.666