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_7158664
_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         'C19 H27 N3'
_chemical_formula_sum            'C19 H27 N3'
_chemical_formula_weight         297.43
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_block_doi                 10.5517/ccdc.csd.cc29hxc3
_audit_creation_date             2021-10-08
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-12-22 deposited with the CCDC.	2022-05-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.6026(2)
_cell_length_b                   12.0411(3)
_cell_length_c                   14.2206(4)
_cell_measurement_reflns_used    6112
_cell_measurement_temperature    100.0(3)
_cell_measurement_theta_max      77.1700
_cell_measurement_theta_min      5.8860
_cell_volume                     1644.27(7)
_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 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.0(3)
_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 0.999
_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    -71.00  22.00   0.50    0.30    --  -47.10  93.00  93.00  186
  2  \w   -176.00 -92.00   0.50    1.50    -- -106.00 -44.00  91.00  168
  3  \w   -139.00 -84.00   0.50    1.50    -- -106.00 -93.00 -18.00  110
  4  \w     45.00 101.00   0.50    1.50    --  113.25 -92.00-119.00  112
  5  \w    -24.00  22.00   0.50    0.30    --   47.10 -19.00-150.00   92
  6  \w    -25.00  22.00   0.50    0.30    --   47.10 -19.00 -30.00   94
  7  \w    -64.00 -35.00   0.50    1.50    -- -106.00  61.00  90.00   58
  8  \w     42.00  68.00   0.50    1.50    --  113.25 -61.00 -90.00   52
  9  \w     42.00  68.00   0.50    1.50    --  113.25 -61.00-180.00   52
 10  \w     62.00 101.00   0.50    1.50    --  113.25 -94.00 150.00   78
 11  \w     45.00  70.00   0.50    1.50    --  113.25 -61.00  60.00   50
 12  \w     43.00 111.00   0.50    1.50    --  113.25-125.00  30.00  136
 13  \w     43.00  71.00   0.50    1.50    --  113.25 -94.00 -90.00   56
 14  \w     84.00 137.00   0.50    1.50    --  113.25  92.00  -6.00  106
 15  \w    -13.00  16.00   0.50    0.30    --  -47.10  19.00-180.00   58
 16  \w   -104.00 -74.00   0.50    0.30    --  -47.10-125.00-150.00   60
 17  \w   -149.00 -99.00   0.50    1.50    -- -106.00 -77.00 -30.00  100
 18  \w   -176.00-151.00   0.50    1.50    -- -106.00 -45.00 -90.00   50
 19  \w   -172.00-120.00   0.50    1.50    -- -106.00 -45.00-180.00  104
 20  \w    -95.00 -49.00   0.50    1.50    -- -106.00  77.00  60.00   92
 21  \w   -121.00 -93.00   0.50    1.50    -- -106.00 -45.00 -90.00   56
 22  \w    -71.00 -39.00   0.50    1.50    -- -106.00  77.00  90.00   64
 23  \w   -100.00 -74.00   0.50    1.50    -- -106.00  77.00  90.00   52
 24  \w     73.00 104.00   0.50    1.50    --  113.25 -94.00-180.00   62
 25  \w     43.00  69.00   0.50    1.50    --  113.25 -61.00-150.00   52
 26  \w    149.00 176.00   0.50    1.50    --  113.25  45.00  60.00   54
 27  \w    107.00 133.00   0.50    1.50    --  113.25  45.00  60.00   52
;
_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      -0.0852714000
_diffrn_orient_matrix_UB_12      -0.0533579000
_diffrn_orient_matrix_UB_13      0.0798354000
_diffrn_orient_matrix_UB_21      0.0205700000
_diffrn_orient_matrix_UB_22      0.1050526000
_diffrn_orient_matrix_UB_23      0.0603019000
_diffrn_orient_matrix_UB_31      -0.1342996000
_diffrn_orient_matrix_UB_32      0.0498258000
_diffrn_orient_matrix_UB_33      -0.0416151000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0331
_diffrn_reflns_av_unetI/netI     0.0354
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            10544
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         69.960
_diffrn_reflns_theta_min         5.559
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.546
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70132
_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    1.202
_exptl_crystal_description       prism
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.175
_refine_diff_density_min         -0.165
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details
;
 Flack x determined using 1159 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.2(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         3091
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0366
_refine_ls_R_factor_gt           0.0335
_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^)+(0.0612P)^2^+0.0672P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0900
_refine_ls_wR_factor_ref         0.0918
_reflns_Friedel_coverage         0.724
_reflns_Friedel_fraction_full    0.982
_reflns_Friedel_fraction_max     0.980
_reflns_number_gt                2876
_reflns_number_total             3091
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ob00674j2.cif
_cod_data_source_block           20015_lja-6_auto
_cod_database_code               7158664
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C19 H27 N3'
_shelx_estimated_absorpt_t_max   0.947
_shelx_estimated_absorpt_t_min   0.899
_reflns_odcompleteness_completeness 99.68
_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
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B)
2.c Aromatic/amide H refined with riding coordinates:
 C9(H9), C12(H12), C8(H8), C11(H11), C7(H7)
2.d Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C19(H19A,H19B,
 H19C), C17(H17A,H17B,H17C), C18(H18A,H18B,H18C)
;
_shelx_res_checksum              3658
_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 1.581
_oxdiff_exptl_absorpt_empirical_full_min 0.608