Nitrogen atom insertion into indenes to access isoquinolines.
Finkelstein, Patrick; Reisenbauer, Julia C.; Botlik, Bence B.; Green, Ori; Florin, Andri; Morandi, Bill; Chemical science 14 (2023) 2954–2959; doi:10.1039/d2sc06952k

data_1568526
_publ_section_title
;
 Nitrogen atom insertion into indenes to access isoquinolines.
;
_journal_issue                   11
_journal_name_full               'Chemical science'
_journal_page_first              2954
_journal_page_last               2959
_journal_paper_doi               10.1039/d2sc06952k
_journal_volume                  14
_journal_year                    2023
_chemical_formula_moiety         'C22 H15 N O'
_chemical_formula_sum            'C22 H15 N O'
_chemical_formula_weight         309.35
_chemical_name_systematic        (4-(isoquinolin-1-yl)phenyl)(phenyl)methanone
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-11-04
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2022-11-24 deposited with the CCDC.	2023-02-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 104.498(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.8089(3)
_cell_length_b                   8.7371(2)
_cell_length_c                   18.3869(5)
_cell_measurement_reflns_used    9139
_cell_measurement_temperature    100.0(1)
_cell_measurement_theta_max      78.0250
_cell_measurement_theta_min      5.6340
_cell_volume                     1525.60(7)
_computing_cell_refinement       'CrysAlisPro 1.171.42.61a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.61a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.61a (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_environment      N~2~
_diffrn_ambient_temperature      100.0(1)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.988
_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   -107.00 -47.00   0.50    0.46    --  -49.37 -76.00 -67.00  120
  2  \w    -63.00  23.00   0.50    0.46    --  -49.37  76.00  58.00  172
  3  \w    -18.00  59.00   0.50    0.46    --   49.37 -76.00 -67.00  154
  4  \w     51.00  76.00   0.50    0.46    --   49.37  76.00  58.00   50
  5  \w    -84.00 -59.00   0.50    1.38    --  -90.00  76.00  58.00   50
  6  \w   -106.00 -80.00   0.50    1.38    --  -90.00 -76.00 -67.00   52
  7  \w     91.00 177.00   0.50    1.38    --  111.50  76.00  58.00  172
  8  \w     42.00  91.00   0.50    1.38    --  111.50 -76.00 -67.00   98
  9  \w   -107.00 -81.00   0.50    0.46    --  -49.37-125.00-180.00   52
 10  \w   -112.00 -74.00   0.50    0.46    --  -49.37-125.00  90.00   76
 11  \w    -15.00  22.00   0.50    0.46    --  -49.37  19.00  60.00   74
 12  \w   -141.00 -86.00   0.50    1.38    --  -90.00 -30.00 150.00  110
 13  \w    -51.00 -26.00   0.50    1.38    --  -90.00  45.00-120.00   50
 14  \w   -137.00 -96.00   0.50    1.38    --  -90.00 -15.00-180.00   82
 15  \w    -51.00 -26.00   0.50    1.38    --  -90.00  45.00 -90.00   50
 16  \w    141.00 171.00   0.50    1.38    --  111.50  61.00 150.00   60
 17  \w     98.00 133.00   0.50    1.38    --  111.50  61.00 150.00   70
 18  \w    105.00 150.00   0.50    1.38    --  111.50  30.00 -30.00   90
 19  \w     85.00 111.00   0.50    1.38    --  111.50-125.00  30.00   52
 20  \w    104.00 156.00   0.50    1.38    --  111.50  15.00-180.00  104
 21  \w     97.00 129.00   0.50    1.38    --  111.50  77.00  90.00   64
 22  \w     41.00 105.00   0.50    1.38    --  111.50 -95.00-180.00  128
 23  \w     43.00  68.00   0.50    1.38    --  111.50-125.00  30.00   50
 24  \w     45.00  91.00   0.50    1.38    --  111.50-125.00  60.00   92
 25  \w    104.00 177.00   0.50    1.38    --  111.50  77.00  30.00  146
 26  \w    110.00 165.00   0.50    1.38    --  111.50  30.00-150.00  110
 27  \w     41.00  67.00   0.50    1.38    --  111.50 -95.00   0.00   52
 28  \w     45.00 100.00   0.50    1.38    --  111.50 -95.00 120.00  110
 29  \w     41.00  66.00   0.50    1.38    --  111.50 -61.00-150.00   50
 30  \w     76.00 101.00   0.50    1.38    --  111.50-125.00 -30.00   50
 31  \w     41.00 102.00   0.50    1.38    --  111.50 -77.00-150.00  122
 32  \w     98.00 161.00   0.50    1.38    --  111.50  61.00   0.00  126
 33  \w    104.00 138.00   0.50    1.38    --  111.50  30.00-120.00   68
 34  \w    105.00 151.00   0.50    1.38    --  111.50 125.00  90.00   92
 35  \w     41.00  66.00   0.50    1.38    --  111.50 -61.00 -30.00   50
 36  \w    103.00 176.00   0.50    1.38    --  111.50  61.00  90.00  146
 37  \w     42.00  83.00   0.50    1.38    --  111.50 -77.00-180.00   82
 38  \w     71.00  99.00   0.50    1.38    --  111.50 -77.00  30.00   56
 39  \w    104.00 149.00   0.50    1.38    --  111.50  45.00 150.00   90
 40  \w     45.00 108.00   0.50    1.38    --  111.50-125.00  90.00  126
 41  \w     93.00 151.00   0.50    1.38    --  111.50  77.00 -30.00  116
 42  \w     46.00  79.00   0.50    1.38    --  111.50 -77.00-120.00   66
 43  \w    105.00 177.00   0.50    1.38    --  111.50 125.00 150.00  144
 44  \w     42.00  84.00   0.50    1.38    --  111.50 -95.00  30.00   84
 45  \w     43.00  68.00   0.50    1.38    --  111.50 -61.00  60.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0882562000
_diffrn_orient_matrix_UB_12      0.1462508000
_diffrn_orient_matrix_UB_13      0.0010885000
_diffrn_orient_matrix_UB_21      0.0520146000
_diffrn_orient_matrix_UB_22      -0.0113575000
_diffrn_orient_matrix_UB_23      0.0861297000
_diffrn_orient_matrix_UB_31      0.1257302000
_diffrn_orient_matrix_UB_32      -0.0978655000
_diffrn_orient_matrix_UB_33      -0.0084711000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0557
_diffrn_reflns_av_unetI/netI     0.0365
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            21147
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         80.327
_diffrn_reflns_theta_min         4.656
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.646
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.717
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.61a (Rigaku Oxford Diffraction, 2022)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.347
_exptl_crystal_description       plate
_exptl_crystal_F_000             648
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Ethyl acetate and hexane'
_exptl_crystal_size_max          0.154
_exptl_crystal_size_mid          0.133
_exptl_crystal_size_min          0.058
_refine_diff_density_max         0.565
_refine_diff_density_min         -0.402
_refine_diff_density_rms         0.110
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.143
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         3303
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.143
_refine_ls_R_factor_all          0.0803
_refine_ls_R_factor_gt           0.0752
_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^)+(0.1215P)^2^+2.2451P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2394
_refine_ls_wR_factor_ref         0.2429
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2943
_reflns_number_total             3303
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2sc06952k2.cif
_cod_data_source_block           bm041122_1_1
_cod_depositor_comments
'Adding full bibliography for 1568525--1568526.cif.'
_cod_database_code               1568526
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C11 H10 N O'
_chemical_oxdiff_usercomment
'yellow plate, from Py/Et2O at -35 degree Celsius.'
_shelx_estimated_absorpt_t_max   0.962
_shelx_estimated_absorpt_t_min   0.909
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C7(H7), C9(H9), C10(H10), C12(H12), C13(H13),
 C15(H15), C16(H16), C18(H18), C19(H19), C20(H20), C21(H21)
;
_shelx_res_checksum              93985
_shelx_hkl_checksum              53426
_olex2_date_sample_data_collection 2022-11-02
_olex2_date_sample_submission    2022-11-02
_olex2_submission_original_sample_id bm041122_1_1
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.635
_oxdiff_exptl_absorpt_empirical_full_min 0.748