An environmentally benign and atom-economical protocol for the regioselective synthesis of isoquinolones from o-alkynylaldehydes
Muskan,; Verma, Akhilesh K.; Green Chemistry 26 (2024) 1297–1301; doi:10.1039/D3GC04096H

data_7247883
_publ_section_title
;
 An environmentally benign and atom-economical protocol for the
 regioselective synthesis of isoquinolones from o-alkynylaldehydes
;
_journal_issue                   3
_journal_name_full               'Green Chemistry'
_journal_page_first              1297
_journal_page_last               1301
_journal_paper_doi               10.1039/D3GC04096H
_journal_volume                  26
_journal_year                    2024
_chemical_formula_moiety         'C23 H26 I N O2'
_chemical_formula_sum            'C23 H26 I N O2'
_chemical_formula_weight         475.35
_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_Hall           'P -2yc'
_space_group_name_H-M_alt        'P 1 c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2023-10-16
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2023-10-16 deposited with the CCDC.	2023-12-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 113.787(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.95427(16)
_cell_length_b                   13.54255(18)
_cell_length_c                   9.03971(16)
_cell_measurement_reflns_used    29587
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      30.8290
_cell_measurement_theta_min      3.8760
_cell_volume                     1003.07(3)
_computing_cell_refinement       'CrysAlisPro 1.171.42.69a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.69a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.69a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2016/4 (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.901
_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    -67.00  19.00   0.50    0.25    --    5.37 -38.00-150.00  172
  2  \w    -67.00  19.00   0.50    0.25    --    5.37 -38.00 -90.00  172
  3  \w    -67.00  19.00   0.50    0.25    --    5.37 -38.00 -30.00  172
  4  \w    -70.00  19.00   0.50    0.25    --    5.37 -25.00 -67.06  178
  5  \w    -70.00  18.00   0.50    0.25    --    5.37 -19.00   0.00  176
  6  \w    -67.00  19.00   0.50    0.25    --    5.37 -38.00  60.00  172
  7  \w    -69.00  19.00   0.50    0.25    --    5.37 -28.00 169.63  176
  8  \w    -70.00  18.00   0.50    0.25    --    5.37 -19.00 120.00  176
  9  \w    -70.00  18.00   0.50    0.25    --    5.37 -19.00  90.00  176
 10  \w     -7.00  81.00   0.50    0.25    --    5.37  19.00 -30.00  176
 11  \w    -18.00  25.00   0.50    0.25    --   -5.21  31.00-125.69   86
 12  \w    -23.00  27.00   0.50    0.25    --   -5.21 -99.00-150.00  100
 13  \w    -23.00  27.00   0.50    0.25    --   -5.21 -99.00   0.00  100
 14  \w    -23.00  27.00   0.50    0.25    --   -5.21 -99.00  30.00  100
 15  \w    -23.00  38.00   0.50    0.25    --    5.37 -99.00 120.00  122
 16  \w    -23.00  27.00   0.50    0.25    --   -5.21 -99.00 120.00  100
 17  \w    -23.00  27.00   0.50    0.25    --   -5.21 -99.00 -90.00  100
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'XtaLAB Synergy, Single source at home/near, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0837370000
_diffrn_orient_matrix_UB_12      -0.0081272000
_diffrn_orient_matrix_UB_13      0.0492615000
_diffrn_orient_matrix_UB_21      -0.0100915000
_diffrn_orient_matrix_UB_22      -0.0510525000
_diffrn_orient_matrix_UB_23      -0.0189813000
_diffrn_orient_matrix_UB_31      0.0195766000
_diffrn_orient_matrix_UB_32      0.0084349000
_diffrn_orient_matrix_UB_33      -0.0675453000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0474
_diffrn_reflns_av_unetI/netI     0.0278
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.901
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            43708
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.845
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.957
_diffrn_reflns_theta_min         3.093
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    1.614
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.76079
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.69a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear brownish colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   brownish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.574
_exptl_crystal_description       block
_exptl_crystal_F_000             480
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.335
_refine_diff_density_min         -0.391
_refine_diff_density_rms         0.069
_refine_ls_abs_structure_details
;
 Flack x determined using 2379 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.053(10)
_refine_ls_extinction_coef       0.0021(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/4 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     249
_refine_ls_number_reflns         5380
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0217
_refine_ls_R_factor_gt           0.0207
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0217P)^2^+0.3240P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0440
_refine_ls_wR_factor_ref         0.0449
_reflns_Friedel_coverage         0.871
_reflns_Friedel_fraction_full    0.981
_reflns_Friedel_fraction_max     0.789
_reflns_number_gt                5248
_reflns_number_total             5380
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3gc04096h2.cif
_cod_data_source_block           msh-u_auto
_cod_depositor_comments          'Adding full bibliography for 7247883.cif.'
_cod_database_code               7247883
_shelx_shelxl_version_number     2016/4
_chemical_oxdiff_formula         'C H N O I'
_chemical_oxdiff_usercomment     11-03-2023
_reflns_odcompleteness_completeness 98.44
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C23(H23A,H23B), C24(H24A,H24B), C25(H25A,H25B), C22(H22A,H22B)
2.b Aromatic/amide H refined with riding coordinates:
 C16(H16), C15(H15), C3(H3), C6(H6), C4(H4), C5(H5), C12(H12), C13(H13)
2.c Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C19(H19A,H19B,H19C), C20(H20A,H20B,H20C)
2.d Idealised tetrahedral OH refined as rotating group:
 O26(H26)
;
_shelx_res_checksum              55382
_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 1.185
_oxdiff_exptl_absorpt_empirical_full_min 0.541