peri-Interactions in 1,8-bis(dimethylamino)naphthalene ortho-ketimine cations facilitate [1,5]-hydride shift: selective synthesis of 1,2,3,4-tetrahydrobenzo[h]quinazolines
Mikshiev, Vladimir Y.; Tolstoy, Peter; Puzyk, Aleksandra M.; Kirichenko, Sergey O.; Antonov, Alexander S.; Organic & Biomolecular Chemistry  (2022) –; doi:10.1039/D2OB00674J

data_7158665
_publ_section_title
;
 peri-Interactions in 1,8-bis(dimethylamino)naphthalene ortho-ketimine
 cations facilitate [1,5]-hydride shift: selective synthesis of
 1,2,3,4-tetrahydrobenzo[h]quinazolines
;
_journal_name_full               'Organic &amp; Biomolecular Chemistry'
_journal_paper_doi               10.1039/D2OB00674J
_journal_year                    2022
_chemical_formula_moiety         'C25 H25 N3'
_chemical_formula_sum            'C25 H25 N3'
_chemical_formula_weight         367.48
_chemical_name_systematic
N,N,1-trimethyl-4-(naphthalen-1-yl)-1,2,3,4-tetrahydrobenzo[h]quinazolin-10-amine
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_block_doi                 10.5517/ccdc.csd.cc29hy0s
_audit_creation_date             2021-12-22
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2021-12-22 deposited with the CCDC.	2022-05-04 downloaded from the CCDC.
;
_cell_angle_alpha                72.713(2)
_cell_angle_beta                 89.359(2)
_cell_angle_gamma                80.928(2)
_cell_formula_units_Z            2
_cell_length_a                   8.9740(3)
_cell_length_b                   10.1567(3)
_cell_length_c                   11.2275(3)
_cell_measurement_reflns_used    8061
_cell_measurement_temperature    99.8(9)
_cell_measurement_theta_max      78.1100
_cell_measurement_theta_min      4.1410
_cell_volume                     964.20(5)
_computing_cell_refinement       'CrysAlisPro 1.171.41.118a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.118a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.118a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_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 0.998
_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     34.00 119.00   0.50    0.18    --   47.10  57.00 -30.00  170
  2  \w     86.00 159.00   0.50    0.80    --  113.25 103.00 -80.00  146
  3  \w    100.00 177.00   0.50    0.80    --  113.25  61.00 -30.00  154
  4  \w    130.00 168.00   0.50    0.80    --  113.25  45.00   0.00   76
  5  \w    102.00 173.00   0.50    0.80    --  113.25  15.00  90.00  142
  6  \w   -104.00 -33.00   0.50    0.80    -- -106.00  77.00 120.00  142
  7  \w    -71.00 -39.00   0.50    0.80    -- -106.00  61.00  60.00   64
  8  \w    -68.00 -43.00   0.50    0.80    -- -106.00  61.00  90.00   50
  9  \w    -80.00 -34.00   0.50    0.80    -- -106.00 125.00 120.00   92
 10  \w   -108.00 -82.00   0.50    0.80    -- -106.00 125.00 120.00   52
 11  \w   -112.00 -86.00   0.50    0.80    -- -106.00 125.00  60.00   52
 12  \w    -61.00 -36.00   0.50    0.80    -- -106.00 125.00  60.00   50
 13  \w    -58.00 -33.00   0.50    0.80    -- -106.00 110.00  21.40   50
 14  \w   -108.00 -73.00   0.50    0.80    -- -106.00 110.00  21.40   70
 15  \w   -106.00 -64.00   0.50    0.80    -- -106.00 108.00 119.29   84
 16  \w   -112.00 -38.00   0.50    0.80    -- -106.00 125.00 -60.00  148
 17  \w   -109.00 -82.00   0.50    0.80    -- -106.00 125.00 -90.00   54
 18  \w    -67.00 -35.00   0.50    0.80    -- -106.00 125.00 -90.00   64
 19  \w    -61.00 -36.00   0.50    0.80    -- -106.00 106.00-159.81   50
 20  \w   -107.00 -81.00   0.50    0.80    -- -106.00 106.00-159.81   52
 21  \w   -106.00 -73.00   0.50    0.80    -- -106.00 103.00 -80.00   66
 22  \w    -64.00 -24.00   0.50    0.18    --  -47.10 103.00 -80.00   80
 23  \w   -154.00 -93.00   0.50    0.80    -- -106.00 -30.00-120.00  122
 24  \w   -174.00-119.00   0.50    0.80    -- -106.00 -45.00-150.00  110
 25  \w   -175.00-120.00   0.50    0.80    -- -106.00 -45.00 -60.00  110
 26  \w   -140.00 -85.00   0.50    0.80    -- -106.00-103.00 176.00  110
 27  \w   -105.00 -78.00   0.50    0.18    --  -47.10-125.00 -30.00   54
 28  \w   -114.00 -73.00   0.50    0.18    --  -47.10-125.00 -60.00   82
 29  \w    -22.00  25.00   0.50    0.18    --   47.10 -19.00  90.00   94
 30  \w     42.00  67.00   0.50    0.80    --  113.25 -61.00  60.00   50
 31  \w     43.00  69.00   0.50    0.80    --  113.25 -61.00   0.00   52
 32  \w     43.00  70.00   0.50    0.80    --  113.25 -61.00 -30.00   54
 33  \w    -24.00  62.00   0.50    0.18    --   47.10 -57.00-150.00  172
 34  \w     45.00 105.00   0.50    0.80    --  113.25 -77.00-180.00  120
 35  \w     46.00  71.00   0.50    0.80    --  113.25 -61.00-150.00   50
 36  \w     48.00  92.00   0.50    0.18    --   47.10-125.00-180.00   88
 37  \w     43.00 108.00   0.50    0.80    --  113.25-125.00 -60.00  130
 38  \w     43.00  82.00   0.50    0.80    --  113.25-125.00 -30.00   78
 39  \w     48.00  77.00   0.50    0.80    --  113.25 -94.00-180.00   58
 40  \w     52.00 105.00   0.50    0.80    --  113.25 -94.00   0.00  106
 41  \w     79.00 106.00   0.50    0.80    --  113.25 -94.00-180.00   54
 42  \w     70.00 108.00   0.50    0.80    --  113.25-111.00  16.51   76
 43  \w     -5.00  81.00   0.50    0.18    --   47.10-103.00 176.00  172
 44  \w     53.00  79.00   0.50    0.80    --  113.25-103.00 176.00   52
 45  \w     62.00 102.00   0.50    0.80    --  113.25 -94.00 120.00   80
;
_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      0.0658300000
_diffrn_orient_matrix_UB_12      -0.0772107000
_diffrn_orient_matrix_UB_13      -0.0927306000
_diffrn_orient_matrix_UB_21      -0.1142470000
_diffrn_orient_matrix_UB_22      0.0970646000
_diffrn_orient_matrix_UB_23      -0.1021161000
_diffrn_orient_matrix_UB_31      0.1134861000
_diffrn_orient_matrix_UB_32      0.1026123000
_diffrn_orient_matrix_UB_33      -0.0406702000
_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  0.0314
_diffrn_reflns_av_unetI/netI     0.0345
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            11725
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         69.996
_diffrn_reflns_theta_min         4.127
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.577
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.92942
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.118a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.266
_exptl_crystal_description       prism
_exptl_crystal_F_000             392
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: n-hexane'
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.545
_refine_diff_density_min         -0.193
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     267
_refine_ls_number_reflns         3647
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0469
_refine_ls_R_factor_gt           0.0420
_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^)+(0.0668P)^2^+0.2484P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1144
_refine_ls_wR_factor_ref         0.1199
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3214
_reflns_number_total             3647
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ob00674j2.cif
_cod_data_source_block           20081_lja-7
_cod_database_code               7158665
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C25 H25 N3'
_shelx_estimated_absorpt_t_max   0.955
_shelx_estimated_absorpt_t_min   0.934
_reflns_odcompleteness_completeness 99.71
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     72.42
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C12(H12)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B)
2.c Aromatic/amide H refined with riding coordinates:
 C10(H10), C16(H16), C21(H21), C9(H9), C5(H5), C15(H15), C6(H6), C18(H18),
 C19(H19), C20(H20)
2.d Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C), C25(H25A,H25B,H25C), C24(H24A,H24B,H24C)
;
_shelx_res_checksum              13759
_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 1.459
_oxdiff_exptl_absorpt_empirical_full_min 0.784