Scaffold Diversity through a Branching Double-Annulation Cascade Strategy: Iminium-Induced One-Pot Synthesis of Diverse Fused Tetrahydroisoquinoline Scaffolds.
Sharada, Duddu S.; Shinde, Anand H.; Patel, Srilaxmi M.; Vidyacharan, Shinde; The Journal of organic chemistry 81 (2016) 6463–6471; doi:10.1021/acs.joc.6b01096

data_4036966
_publ_section_title
;
 Scaffold Diversity through a Branching Double-Annulation Cascade
 Strategy: Iminium-Induced One-Pot Synthesis of Diverse Fused
 Tetrahydroisoquinoline Scaffolds.
;
_journal_issue                   15
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              6463
_journal_page_last               6471
_journal_paper_doi               10.1021/acs.joc.6b01096
_journal_volume                  81
_journal_year                    2016
_chemical_formula_moiety         'C23 H19 Cl N2 O'
_chemical_formula_sum            'C23 H19 Cl N2 O'
_chemical_formula_weight         374.87
_chemical_name_systematic
5-benzyl-8-chloro-12,13-dihydro-4bH-isoquinolino[2,1-a]quinazolin-6(5H)-one
_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'
_symmetry_Int_Tables_number      14
_atom_sites_solution_primary     direct
_audit_creation_date             2016-05-06
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Olex2 1.2
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_computing_cell_refinement
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CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
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  1 omega  -79.00  -54.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
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  2 omega  -98.00  -62.00   1.0000    1.5000
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omega____ theta____ kappa____ phi______ frames
    -      -33.5000  178.0000   90.0000 25

  4 omega  -86.00  -42.00   1.0000    1.5000
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    -      -33.5000  125.0000  -60.0000 44

  5 omega  -60.00  -23.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  -57.0000   30.0000 37

  6 omega   42.00  119.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   38.0000   90.0000 77

  7 omega   34.00  124.00   1.0000    1.5000
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  8 omega   25.00  108.00   1.0000    1.5000
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  9 omega   46.00  136.00   1.0000    1.5000
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 10 omega   37.00   62.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000 -120.0000 25

 11 omega   41.00   89.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000 -180.0000 48

 12 omega   89.00  169.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   50.0000   90.0000 80

 13 omega  104.00  176.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
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 14 omega   39.00   86.00   1.0000    1.5000
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 15 omega   59.00  106.00   1.0000    1.5000
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    -      108.0000  -63.0000   60.0000 47

 16 omega   38.00   93.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000  -30.0000 55

 17 omega   39.00   73.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -50.0000 -180.0000 34
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_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
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_diffrn_orient_matrix_UB_22      0.1339550000
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_diffrn_orient_matrix_UB_31      0.0438220000
_diffrn_orient_matrix_UB_32      0.0767441000
_diffrn_orient_matrix_UB_33      0.0900809000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
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_diffrn_reflns_av_R_equivalents  0.0287
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_diffrn_reflns_limit_h_min       -16
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_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            7614
_diffrn_reflns_theta_full        70.7724
_diffrn_reflns_theta_max         70.77
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_diffrn_source                   'SuperNova (Cu) X-ray Source'
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CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
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_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
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_exptl_crystal_density_diffrn    1.3364
_exptl_crystal_description       needle
_exptl_crystal_F_000             787.5997
_exptl_crystal_preparation       'Recrystalization from DCM'
_exptl_crystal_recrystallization_method 'Recrystalization from DCM'
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_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
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_refine_ls_structure_factor_coef Fsqd
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'w=1/[\s^2^(Fo^2^)+(0.0618P)^2^+0.1169P] where P=(Fo^2^+2Fc^2^)/3'
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_cod_data_source_file            jo6b01096_si_002.cif
_cod_data_source_block           exp_4504
_cod_original_sg_symbol_Hall     '-P 2ybc (x-z,y,z)'
_cod_database_code               4036966
_chemical_oxdiff_formula         'C23 H19 N2 O Cl'
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H) groups
2. Rigid bond restraints
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3.a Ternary CH refined with riding coordinates:
 C5(H5)
3.b Secondary CH2 refined with riding coordinates:
 C17(H17a,H17b), C10(H10a,H10b)
3.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C8(H8), C13(H13), C16(H16), C7(H7), C15(H15), C23(H23), C14(H14),
 C19(H19), C22(H22), C20(H20), C21(H21)
;
_olex2_submission_special_instructions 'No special instructions were received'