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_4036968
_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         'C15 H14 N2 O2 S'
_chemical_formula_sum            'C15 H14 N2 O2 S'
_chemical_formula_weight         286.36
_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             2016-05-08
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_cell_angle_alpha                90
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_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.9410(4)
_cell_length_b                   11.9290(5)
_cell_length_c                   13.9233(7)
_cell_measurement_reflns_used    1941
_cell_measurement_temperature    293
_cell_measurement_theta_max      70.6522
_cell_measurement_theta_min      3.1714
_cell_volume                     1318.93(11)
_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 1.0000
_diffrn_measured_fraction_theta_max 1.0000
_diffrn_measurement_details
;
  1 omega  -88.00  -11.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  -38.0000 -180.0000 77

  2 omega  -67.00  -35.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  178.0000  -30.0000 32

  3 omega   70.00  118.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   77.0000  -90.0000 48

  4 omega   30.00   70.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -57.0000  -90.0000 40

  5 omega   26.00   67.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   77.0000  -90.0000 41

  6 omega   39.00  137.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000 -150.0000 98

  7 omega   38.00   66.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000 -180.0000 28

  8 omega   38.00   63.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000  -60.0000 25

  9 omega   37.00   85.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000 -150.0000 48

 10 omega   42.00   93.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000   30.0000 51

 11 omega   37.00   62.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000  150.0000 25

 12 omega   44.00   92.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000  -30.0000 48
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0445405000
_diffrn_orient_matrix_UB_12      -0.0619715000
_diffrn_orient_matrix_UB_13      0.0936491000
_diffrn_orient_matrix_UB_21      0.1711841000
_diffrn_orient_matrix_UB_22      -0.0605853000
_diffrn_orient_matrix_UB_23      -0.0027069000
_diffrn_orient_matrix_UB_31      0.0796770000
_diffrn_orient_matrix_UB_32      0.0957742000
_diffrn_orient_matrix_UB_33      0.0588302000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0204
_diffrn_reflns_av_unetI/netI     0.0317
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            3421
_diffrn_reflns_theta_full        70.7880
_diffrn_reflns_theta_max         70.79
_diffrn_reflns_theta_min         4.88
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.209
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83931
_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            'light yellow'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.4420
_exptl_crystal_description       needle
_exptl_crystal_F_000             603.0824
_exptl_crystal_size_max          0.06
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.5570
_refine_diff_density_min         -0.4020
_refine_diff_density_rms         0.0557
_refine_ls_abs_structure_details
'Flack, H. D. (1983). Acta Cryst. A39, 876-881.'
_refine_ls_abs_structure_Flack   0.47(9)
_refine_ls_d_res_high            0.8164
_refine_ls_d_res_low             9.0589
_refine_ls_goodness_of_fit_ref   1.0610
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    25
_refine_ls_number_parameters     183
_refine_ls_number_reflns         2073
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0610
_refine_ls_R_factor_all          0.0627
_refine_ls_R_factor_gt           0.0609
_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^)+(0.0880P)^2^+0.9850P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1603
_refine_ls_wR_factor_ref         0.1628
_reflns_Friedel_coverage         0.584
_reflns_limit_h_max              9
_reflns_limit_h_min              -9
_reflns_limit_k_max              14
_reflns_limit_k_min              -14
_reflns_limit_l_max              16
_reflns_limit_l_min              -16
_reflns_number_gt                1985
_reflns_number_total             2073
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            jo6b01096_si_003.cif
_cod_data_source_block           exp_4503
_cod_original_cell_volume        1318.94(11)
_cod_original_sg_symbol_Hall     ' P 2ac 2ab'
_cod_database_code               4036968
_chemical_oxdiff_formula         'C15 H14 N S O2'
_reflns_odcompleteness_completeness 99.93
_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 N(H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7a,H7b), C0aa(H0aa,H0ab)
2.c Aromatic/amide H refined with riding coordinates:
 C14(H14), C11(H11), C12(H12), C13(H13), C3(H3), C2(H2), C19(H19), C4(H4)
;
_olex2_submission_special_instructions 'No special instructions were received'