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_7160611
_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         'I, C15 H11 Br N'
_chemical_formula_sum            'C15 H11 Br I N'
_chemical_formula_weight         412.06
_chemical_melting_point          507.9
_chemical_name_systematic        '2-(4-bromophenyl)isoquinolin-2-ium iodide'
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2025-02-07
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2025-02-21 deposited with the CCDC.	2025-06-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 106.994(12)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.7506(11)
_cell_length_b                   11.3088(13)
_cell_length_c                   13.4947(17)
_cell_measurement_reflns_used    2942
_cell_measurement_temperature    294.45(11)
_cell_measurement_theta_max      26.0810
_cell_measurement_theta_min      2.2280
_cell_volume                     1423.1(3)
_computing_cell_refinement       'CrysAlisPro 1.171.42.81a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.81a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.81a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      294.45(11)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4471
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.866
_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    -62.00 -10.00   1.00    1.00    --   12.87 -37.00 -90.00   52
  2  \w    -41.00 -14.00   1.00    1.00    --  -13.65  77.00 -30.00   27
  3  \w    -18.00  26.00   1.00    1.00    --  -13.65 -99.00  90.00   44
  4  \w    -38.00  43.00   1.00    1.00    --  -13.65  37.00-120.00   81
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0080213000
_diffrn_orient_matrix_UB_12      -0.0544885000
_diffrn_orient_matrix_UB_13      -0.0237937000
_diffrn_orient_matrix_UB_21      -0.0110511000
_diffrn_orient_matrix_UB_22      -0.0310946000
_diffrn_orient_matrix_UB_23      0.0426776000
_diffrn_orient_matrix_UB_31      -0.0747973000
_diffrn_orient_matrix_UB_32      -0.0012527000
_diffrn_orient_matrix_UB_33      -0.0251184000
_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  0.0464
_diffrn_reflns_av_unetI/netI     0.0712
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.866
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            8125
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.866
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.497
_diffrn_reflns_theta_min         2.290
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    5.040
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.22425
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.81a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_density_diffrn    1.923
_exptl_crystal_description       plate
_exptl_crystal_F_000             784
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.656
_refine_diff_density_min         -1.043
_refine_diff_density_rms         0.191
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         3752
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0912
_refine_ls_R_factor_gt           0.0478
_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^)+(0.0442P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0924
_refine_ls_wR_factor_ref         0.1190
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2330
_reflns_number_total             3752
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob00634a2.cif
_cod_data_source_block           g240329b_auto
_cod_depositor_comments
'Adding full bibliography for 7160611--7160612.cif.'
_cod_database_code               7160611
_shelx_shelxl_version_number     2019/2
_reflns_odcompleteness_completeness 99.91
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.42
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C8(H8), C12(H12), C11(H11), C7(H7), C6(H6), C14(H14), C13(H13), C1(H1),
 C9(H9), C2(H2), C3(H3)
;
_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 3.001
_oxdiff_exptl_absorpt_empirical_full_min 0.577