Metal-free construction of aminated isoquinoline frameworks from 2-(2-oxo-2-arylethyl) benzonitrile in an aqueous medium
Sharma, Himanshi; Kumar, Manoj; Sethi, Aaftaab; Poonam,; Rathi, Brijesh; Green Chemistry 25 (2023) 167–171; doi:10.1039/D2GC04044A

data_7245974
_publ_section_title
;
 Metal-free construction of aminated isoquinoline frameworks from
 2-(2-oxo-2-arylethyl) benzonitrile in an aqueous medium
;
_journal_issue                   1
_journal_name_full               'Green Chemistry'
_journal_page_first              167
_journal_page_last               171
_journal_paper_doi               10.1039/D2GC04044A
_journal_volume                  25
_journal_year                    2023
_chemical_formula_moiety         'C26 H22 F3 N3'
_chemical_formula_sum            'C26 H22 F3 N3'
_chemical_formula_weight         433.46
_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_block_doi                 10.5517/ccdc.csd.cc2cztz5
_audit_creation_date             2022-08-30
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2022-08-30 deposited with the CCDC.	2022-12-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.165(9)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.7050(10)
_cell_length_b                   16.0805(14)
_cell_length_c                   13.7744(13)
_cell_measurement_reflns_used    2759
_cell_measurement_temperature    298
_cell_measurement_theta_max      23.1680
_cell_measurement_theta_min      2.5890
_cell_volume                     2146.4(4)
_computing_cell_refinement       'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_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      298
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.948
_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    -69.00 119.00   1.00   30.00    --   29.89  54.00-180.00  188
  2  \w    -69.00 119.00   1.00   30.00    --   29.89  54.00-180.00  188
  3  \w    -69.00 119.00   1.00   30.00    --   29.89  54.00 -90.00  188
  4  \w    -69.00 -44.00   1.00   30.00    --   29.89  54.00  30.00   25
;
_diffrn_measurement_device       'two-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Mini (ROW)'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0303453000
_diffrn_orient_matrix_UB_12      -0.0168481000
_diffrn_orient_matrix_UB_13      0.0437516000
_diffrn_orient_matrix_UB_21      -0.0665822000
_diffrn_orient_matrix_UB_22      -0.0057805000
_diffrn_orient_matrix_UB_23      0.0178095000
_diffrn_orient_matrix_UB_31      -0.0032624000
_diffrn_orient_matrix_UB_32      -0.0403099000
_diffrn_orient_matrix_UB_33      -0.0207323000
_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  0.0535
_diffrn_reflns_av_unetI/netI     0.0593
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.948
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            31693
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.948
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.854
_diffrn_reflns_theta_min         2.533
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.66993
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.35c (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_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    1.341
_exptl_crystal_description       block
_exptl_crystal_F_000             904
_exptl_crystal_size_max          0.055
_exptl_crystal_size_mid          0.032
_exptl_crystal_size_min          0.023
_refine_diff_density_max         0.389
_refine_diff_density_min         -0.203
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.992
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     316
_refine_ls_number_reflns         7578
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      0.992
_refine_ls_R_factor_all          0.1980
_refine_ls_R_factor_gt           0.0777
_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^)+(0.1361P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1986
_refine_ls_wR_factor_ref         0.2893
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2743
_reflns_number_total             7578
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2gc04044a2.cif
_cod_data_source_block           m_rt
_cod_depositor_comments          'Adding full bibliography for 7245974.cif.'
_cod_database_code               7245974
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.998
_shelx_estimated_absorpt_t_min   0.995
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Restrained distances
 F5-C1 \\sim F4-C1
 with sigma of 0.02
 F2-C1 \\sim F3-C1
 with sigma of 0.02
 F1-C1 \\sim F6-C1
 with sigma of 0.02
3. Others
 Fixed Sof: F5(0.5) F1(0.5) F2(0.5) F4(0.5) F3(0.5) F6(0.5)
4.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C10(H10A,H10B), C11(H11A,H11B), C8(H8A,H8B)
4.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C19(H19), C3(H3), C14(H14), C26(H26), C17(H17), C6(H6), C15(H15),
 C22(H22), C7(H7), C25(H25), C16(H16), C24(H24), C23(H23)
;
_shelx_res_checksum              62570
_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 1.398
_oxdiff_exptl_absorpt_empirical_full_min 0.837