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_4036967
_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_absolute_configuration unk
_chemical_formula_moiety         'C32 H26 N4 O2'
_chemical_formula_sum            'C32 H26 N4 O2'
_chemical_formula_weight         498.59
_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'
_symmetry_Int_Tables_number      19
_atom_sites_solution_primary     iterative
_audit_creation_date             2016-03-18
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.3261(8)
_cell_length_b                   15.0211(8)
_cell_length_c                   16.2026(9)
_cell_measurement_reflns_used    1411
_cell_measurement_temperature    293
_cell_measurement_theta_max      71.0525
_cell_measurement_theta_min      4.0078
_cell_volume                     2513.2(3)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_reduction
;
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)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_temperature      293
_diffrn_detector_area_resol_mean 16.1293
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 1
_diffrn_measurement_details
;
  1 omega  -35.00   28.00   1.0000    2.1200
omega____ theta____ kappa____ phi______ frames
    -      -42.5000   85.0000 -142.0000 63

  2 omega   12.00   37.00   1.0000    2.1200
omega____ theta____ kappa____ phi______ frames
    -       55.1553  -83.0000   35.0000 25

  3 omega   48.00  138.00   1.0000    2.1200
omega____ theta____ kappa____ phi______ frames
    -      110.3105  -85.0000   98.0000 90

  4 omega   42.00  115.00   1.0000    2.1200
omega____ theta____ kappa____ phi______ frames
    -      110.3105  -56.0000  -39.0000 73

  5 omega  -10.00   22.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   85.0000  -98.0000 32

  6 omega   17.00   42.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   38.0000   60.0000 25

  7 omega  -27.00   29.00   1.0000    2.1200
omega____ theta____ kappa____ phi______ frames
    -      -42.5000   38.0000  120.0000 56

  8 omega  -39.00   27.00   1.0000    2.1200
omega____ theta____ kappa____ phi______ frames
    -      -42.5000   38.0000    0.0000 66

  9 omega   68.00   94.00   1.0000    2.1200
omega____ theta____ kappa____ phi______ frames
    -      110.3105  -50.0000 -120.0000 26

 10 omega   66.00   92.00   1.0000    2.1200
omega____ theta____ kappa____ phi______ frames
    -      110.3105  -25.0000 -150.0000 26

 11 omega   38.00   68.00   1.0000    2.1200
omega____ theta____ kappa____ phi______ frames
    -      110.3105  -38.0000   30.0000 30

 12 omega  101.00  143.00   1.0000    2.1200
omega____ theta____ kappa____ phi______ frames
    -      110.3105  111.0000  120.0000 42

 13 omega   39.00   88.00   1.0000    2.1200
omega____ theta____ kappa____ phi______ frames
    -      110.3105  -50.0000  120.0000 49
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0845849000
_diffrn_orient_matrix_UB_12      0.0839178000
_diffrn_orient_matrix_UB_13      0.0084330000
_diffrn_orient_matrix_UB_21      0.0530099000
_diffrn_orient_matrix_UB_22      0.0347477000
_diffrn_orient_matrix_UB_23      -0.0827629000
_diffrn_orient_matrix_UB_31      -0.1109404000
_diffrn_orient_matrix_UB_32      -0.0474158000
_diffrn_orient_matrix_UB_33      -0.0459787000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0319
_diffrn_reflns_av_unetI/netI     0.0831
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            6242
_diffrn_reflns_theta_full        71.2297
_diffrn_reflns_theta_max         71.23
_diffrn_reflns_theta_min         4.01
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.668
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.50739
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
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.
;
_exptl_crystal_colour            'clear whiteish white'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.3176
_exptl_crystal_description       needle
_exptl_crystal_F_000             1051.2013
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.2545
_refine_diff_density_min         -0.3158
_refine_diff_density_rms         0.0708
_refine_ls_abs_structure_details
'Flack, H. D. (1983). Acta Cryst. A39, 876-881.'
_refine_ls_abs_structure_Flack   0.2(8)
_refine_ls_d_res_high            0.8142
_refine_ls_d_res_low             11.0156
_refine_ls_goodness_of_fit_ref   1.0263
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    48
_refine_ls_number_parameters     342
_refine_ls_number_reflns         4258
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0263
_refine_ls_R_factor_all          0.1106
_refine_ls_R_factor_gt           0.0668
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0780P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1464
_refine_ls_wR_factor_ref         0.1876
_reflns_Friedel_coverage         0.732
_reflns_limit_h_max              12
_reflns_limit_h_min              -12
_reflns_limit_k_max              18
_reflns_limit_k_min              -17
_reflns_limit_l_max              19
_reflns_limit_l_min              -19
_reflns_number_gt                2649
_reflns_number_total             4258
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            jo6b01096_si_004.cif
_cod_data_source_block           exp_5258
_cod_original_sg_symbol_Hall     ' P 2ac 2ab'
_cod_database_code               4036967
_chemical_oxdiff_formula         'C16 H15 N3 O'
_reflns_odcompleteness_completeness 99.84
_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
2.a Ternary CH refined with riding coordinates:
 C8(H8), C17(H17)
2.b Secondary CH2 refined with riding coordinates:
 C16(H16a,H16b), C15(H15a,H15b), C24(H24a,H24b), C25(H25a,H25b)
2.c Aromatic/amide H refined with riding coordinates:
 C10(H10), C11(H11), C12(H12), C13(H13), C3(H3), C4(H4), C5(H5), C6(H6),
 C28(H28), C29(H29), C30(H30), C31(H31), C19(H19), C20(H20), C21(H21), C22(H22)
;
_olex2_submission_special_instructions 'No special instructions were received'