BF3·OEt2 mediated metal-free one-pot sequential multiple annulation cascade (SMAC) synthesis of complex and diverse tetrahydroisoquinoline fused hybrid molecules.
Shinde, Anand H.; Vidyacharan, Shinde; Sharada, Duddu S.; Organic & biomolecular chemistry 14 (2016) 3207–3211; doi:10.1039/c6ob00253f

data_7155003
_publ_section_title
;
 BF3&#x00B7;OEt2 mediated metal-free one-pot sequential multiple
 annulation cascade (SMAC) synthesis of complex and diverse
 tetrahydroisoquinoline fused hybrid molecules.
;
_journal_issue                   12
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              3207
_journal_page_last               3211
_journal_paper_doi               10.1039/c6ob00253f
_journal_volume                  14
_journal_year                    2016
_chemical_formula_moiety         'C24 H20 Br N3'
_chemical_formula_sum            'C24 H20 Br N3'
_chemical_formula_weight         430.35
_chemical_melting_point          483
_chemical_name_systematic
2-Bromo-9,10-dimethyl-6,17c-dihydro-5H-indazolo[2,3-a]isoquinolino[1,2-c]quinoxaline
_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_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_audit_creation_date             2015-12-07
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Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
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_audit_update_record
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2015-12-17 deposited with the CCDC.
2016-02-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 113.032(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
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_cell_length_c                   12.0520(4)
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_cell_measurement_temperature    298
_cell_measurement_theta_max      70.6377
_cell_measurement_theta_min      3.9823
_cell_volume                     1918.96(14)
_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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_diffrn_measured_fraction_theta_max 1.00000
_diffrn_measurement_details
;
  1 omega  -30.00   33.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000   38.0000  -30.0000 63

  2 omega -105.00  -24.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  -12.0000  150.0000 81

  3 omega   35.00  112.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   57.0000   60.0000 77

  4 omega   36.00   96.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       54.0000 -125.0000  150.0000 60

  5 omega   33.00   68.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
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  6 omega   84.00  123.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
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  7 omega   93.00  118.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
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  8 omega   37.00   94.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000  120.0000 57

  9 omega   54.00   79.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000  -90.0000 25

 10 omega  145.00  172.00   1.0000    1.5000
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 11 omega   92.00  122.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   50.0000 -120.0000 30

 12 omega   37.00   68.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000  -90.0000 31

 13 omega   59.00   98.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000    0.0000 39

 14 omega   50.00   94.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000 -180.0000 44

 15 omega   48.00   77.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000  -86.0000 29

 16 omega   42.00  134.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000 -180.0000 92
;
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_diffrn_measurement_method       '\w scans'
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_diffrn_orient_matrix_UB_33      -0.0419865000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0296
_diffrn_reflns_av_unetI/netI     0.0425
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -20
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_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6456
_diffrn_reflns_theta_full        70.773526
_diffrn_reflns_theta_max         70.77
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_diffrn_source                   'SuperNova (Cu) X-ray Source'
_diffrn_source_current           n/a
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_exptl_absorpt_coefficient_mu    3.020
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.65879
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
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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            'light yellow'
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_exptl_crystal_colour_primary    colourless
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_exptl_crystal_F_000             879.3894
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Chloroform'
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_refine_ls_hydrogen_treatment    mixed
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_refine_ls_R_factor_all          0.066179
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_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0733P)^2^+0.9875P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
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_reflns_limit_l_min              -6
_reflns_number_gt                2534
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_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            c6ob00253f2.cif
_cod_data_source_block           exp_4999
_cod_depositor_comments          'Adding full bibliography for 7155003.cif.'
_cod_original_cell_volume        1918.97(15)
_cod_database_code               7155003
_chemical_oxdiff_formula         'C24 H20 N3 Br'
_reflns_odcompleteness_completeness 89.77
_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
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7a,H7b), C8(H8a,H8b)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C6(H6), C13(H13), C14(H14), C15(H15), C16(H16), C19(H19),
 C22(H22)
2.d Idealised Me refined as rotating group:
 C23(H23a,H23b,H23c), C24(H24a,H24b,H24c)
;
_olex2_date_sample_data_collection 1431181998.71
_olex2_submission_special_instructions 'No special instructions were received'