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_1568525
_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         'C9 H6 Br N, H2 O'
_chemical_formula_sum            'C9 H8 Br N O'
_chemical_formula_weight         226.07
_chemical_name_systematic        6-Bromoisoquinoline
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2022-11-07
_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                 94.654(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.0681(5)
_cell_length_b                   4.8252(2)
_cell_length_c                   15.0066(7)
_cell_measurement_reflns_used    6041
_cell_measurement_temperature    100.0(1)
_cell_measurement_theta_max      32.2960
_cell_measurement_theta_min      4.2040
_cell_volume                     870.97(7)
_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 1.5 (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 2014/4 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.0(1)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_detector_type            'Pilatus 200K'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.902
_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     -6.00  83.00   0.50    4.10    --   10.01  57.00   0.00  178
  2  \w     -5.00  89.00   0.50    4.10    --   10.01  38.00 -90.00  188
  3  \w    -27.00  67.00   0.50    4.10    --  -12.04  38.00 -30.00  188
  4  \w    -92.00 -13.00   0.50    4.10    --  -12.04 -19.00-180.00  158
  5  \w    -70.00 -13.00   0.50    4.10    --   10.01 -19.00-120.00  114
  6  \w    -23.00   2.00   0.50    4.10    --   10.01 -99.00 120.00   50
  7  \w    -23.00  43.00   0.50    4.10    --   10.01 -99.00-150.00  132
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, Pilatus 200K'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0582043000
_diffrn_orient_matrix_UB_12      0.0030367000
_diffrn_orient_matrix_UB_13      0.0037466000
_diffrn_orient_matrix_UB_21      -0.0094726000
_diffrn_orient_matrix_UB_22      -0.0064296000
_diffrn_orient_matrix_UB_23      -0.0471999000
_diffrn_orient_matrix_UB_31      -0.0007816000
_diffrn_orient_matrix_UB_32      -0.1468983000
_diffrn_orient_matrix_UB_33      0.0020929000
_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  0.0510
_diffrn_reflns_av_unetI/netI     0.0472
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.902
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            14713
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.902
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         33.108
_diffrn_reflns_theta_min         3.322
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    4.666
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.459
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.69a (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 colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.724
_exptl_crystal_description       needle
_exptl_crystal_F_000             448
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Ethyl acetate and hexane'
_exptl_crystal_size_max          0.261
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.077
_refine_diff_density_max         1.097
_refine_diff_density_min         -1.570
_refine_diff_density_rms         0.143
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     112
_refine_ls_number_reflns         2985
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0618
_refine_ls_R_factor_gt           0.0391
_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^)+(0.0553P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0875
_refine_ls_wR_factor_ref         0.0948
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2239
_reflns_number_total             2985
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2sc06952k2.cif
_cod_data_source_block           bm051122_1_1
_cod_depositor_comments
'Adding full bibliography for 1568525--1568526.cif.'
_cod_database_code               1568525
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C9H6BrN
_shelx_estimated_absorpt_t_max   0.707
_shelx_estimated_absorpt_t_min   0.377
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H,H) groups
2.a Free rotating group:
 O1(H1A,H1B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C7(H7), C9(H9)
;
_shelx_res_checksum              55031
_shelx_hkl_checksum              3883
_olex2_date_sample_data_collection 2022-11-04
_olex2_date_sample_submission    2022-11-02
_olex2_submission_original_sample_id bm051122_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 2.324
_oxdiff_exptl_absorpt_empirical_full_min 0.643