Pseudo-Multicomponent Reactions of Arynes with N-Aryl Imines.
Castillo, Juan-Carlos; Quiroga, Jairo; Abonia, Rodrigo; Rodriguez, Jean; Coquerel, Yoann; The Journal of organic chemistry 80 (2015) 9767–9773; doi:10.1021/acs.joc.5b01564

data_4036325
_publ_section_title
;
 Pseudo-Multicomponent Reactions of Arynes with N-Aryl Imines.
;
_journal_issue                   19
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              9767
_journal_page_last               9773
_journal_paper_doi               10.1021/acs.joc.5b01564
_journal_volume                  80
_journal_year                    2015
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C32 H28 Cl N3'
_chemical_formula_sum            'C32 H28 Cl N3'
_chemical_formula_weight         490.02
_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   geom
_audit_creation_date
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'Wed Apr 30 14:02:07 2014'
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
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_cell_length_c                   23.9164(11)
_cell_measurement_reflns_used    3348
_cell_measurement_temperature    293(2)
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_cell_volume                     2580.3(2)
_computing_cell_refinement
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
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_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
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_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
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_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
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_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3048
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_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_details
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  1 omega  -27.00    6.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   57.0000 -120.0000 33

  2 omega   30.00   77.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   57.0000 -120.0000 47

  3 omega  -48.00   38.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -55.5887   30.0000 -120.0000 86

  4 omega   -4.00  106.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       55.5887  -94.0000  150.0000 110

  5 omega   94.00  148.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       55.5887  125.0000 -150.0000 54

  6 omega   32.00   90.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      111.1773  -25.0000  150.0000 58

  7 omega   81.00  112.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      111.1773 -111.0000 -180.0000 31

  8 omega   23.00  101.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      111.1773  -50.0000  -90.0000 78

  9 omega   37.00  104.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      111.1773 -111.0000  -60.0000 67

 10 omega   28.00   94.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      111.1773  -25.0000   90.0000 66

 11 omega  128.00  174.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      111.1773  111.0000  150.0000 46

 12 omega   18.00   88.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      111.1773  -25.0000   30.0000 70
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_diffrn_measurement_device       'four-circle diffractometer'
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_diffrn_orient_matrix_UB_11      0.0151952000
_diffrn_orient_matrix_UB_12      -0.1118797000
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_diffrn_orient_matrix_UB_21      -0.0093383000
_diffrn_orient_matrix_UB_22      0.0811276000
_diffrn_orient_matrix_UB_23      -0.0522424000
_diffrn_orient_matrix_UB_31      0.1571508000
_diffrn_orient_matrix_UB_32      0.0157304000
_diffrn_orient_matrix_UB_33      0.0005432000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0567
_diffrn_reflns_av_unetI/netI     0.0328
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            14376
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.313
_diffrn_reflns_theta_min         3.696
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.497
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.57335
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_exptl_absorpt_process_details
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
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_exptl_crystal_colour            colorless
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 Classical Flack method preferred over Parsons because s.u. lower.
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_refine_ls_abs_structure_Flack   0.438(16)
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_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
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_refine_ls_number_reflns         11419
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0775
_refine_ls_R_factor_gt           0.0652
_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^)+(0.1277P)^2^+0.1296P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1989
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_cell_oxdiff_length_c            23.9166(14)
_cell_oxdiff_measurement_reflns_used 3348
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_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1)
2.b Aromatic/amide H refined with riding coordinates:
 C24(H24), C3(H3), C18(H18), C22(H22), C4(H4), C25(H25), C6(H6), C12(H12),
 C16(H16), C5(H5), C15(H15), C19(H19), C28(H28), C13(H13), C26(H26), C21(H21),
 C20(H20), C27(H27)
2.c Idealised Me refined as rotating group:
 C32(H32A,H32B,H32C), C31(H31A,H31B,H31C), C30(H30A,H30B,H30C)
;