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_4036326
_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_formula_moiety         'C35 H35 N3 O3'
_chemical_formula_sum            'C35 H35 N3 O3'
_chemical_formula_weight         545.66
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date
;
'Thu Jun 12 16:34:46 2014'
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_audit_creation_method
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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_angle_alpha                90.0
_cell_angle_beta                 91.8720(15)
_cell_angle_gamma                90.0
_cell_formula_units_Z            4
_cell_length_a                   10.63570(16)
_cell_length_b                   10.82044(18)
_cell_length_c                   26.4828(5)
_cell_measurement_reflns_used    5264
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      73.6430
_cell_measurement_theta_min      4.1370
_cell_volume                     3046.09(9)
_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)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3048
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.953
_diffrn_measurement_details
;
  1 omega  -50.00   19.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.0146   38.0000  120.0000 69

  2 omega   24.00   74.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       40.0146 -125.0000  -60.0000 50

  3 omega   33.00   98.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      107.6719  -45.0000   30.0000 65

  4 omega   80.00  178.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      107.6719   45.0000   60.0000 98

  5 omega   77.00  177.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      107.6719   61.0000  150.0000 100

  6 omega   33.00  121.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      107.6719 -125.0000  -60.0000 88

  7 omega  -67.00   36.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.0146   77.0000 -150.0000 103
;
_diffrn_measurement_device       'four-circle diffractometer'
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_diffrn_orient_matrix_UB_11      0.0890833000
_diffrn_orient_matrix_UB_12      -0.0319121000
_diffrn_orient_matrix_UB_13      -0.0428288000
_diffrn_orient_matrix_UB_21      0.0854767000
_diffrn_orient_matrix_UB_22      0.1092514000
_diffrn_orient_matrix_UB_23      0.0157508000
_diffrn_orient_matrix_UB_31      0.0759613000
_diffrn_orient_matrix_UB_32      -0.0855220000
_diffrn_orient_matrix_UB_33      0.0361131000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0143
_diffrn_reflns_av_unetI/netI     0.0262
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.953
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            9809
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.953
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.764
_diffrn_reflns_theta_min         4.159
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.604
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.93397
_exptl_absorpt_correction_type   multi-scan
_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
_exptl_crystal_density_diffrn    1.190
_exptl_crystal_description
;
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_exptl_crystal_F_000             1160
_exptl_crystal_size_max          .16
_exptl_crystal_size_mid          .16
_exptl_crystal_size_min          .12
_refine_diff_density_max         0.514
_refine_diff_density_min         -0.300
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
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_refine_ls_number_reflns         5864
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.0692
_refine_ls_R_factor_gt           0.0609
_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^)+(0.0972P)^2^+0.8233P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1743
_refine_ls_wR_factor_ref         0.1844
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4944
_reflns_number_total             5864
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo5b01564_si_003.cif
_cod_data_source_block           jcc1250
_cod_original_cell_volume        3046.10(9)
_cod_database_code               4036326
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_reflns_odcompleteness_completeness 98.90
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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:
 C5(H5)
2.b Aromatic/amide H refined with riding coordinates:
 C11(H11), C12(H12), C13(H13), C17(H17), C18(H18), C19(H19), C21(H21),
 C24(H24), C25(H25), C26(H26), C27(H27), C28(H28), C30(H30), C31(H31), C33(H33),
  C34(H34)
2.c Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C10(H10A,H10B,H10C), C15(H15A,H15B,H15C),
 C22(H22A,H22B,H22C), C35(H35A,H35B,H35C)
;
_olex2_submission_special_instructions 'No special instructions were received'