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_4036327
_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 H31 N3 O'
_chemical_formula_sum            'C35 H31 N3 O'
_chemical_formula_weight         509.63
_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   mixed
_audit_creation_date
;
'Fri May 09 09:57:57 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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_audit_update_record
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2014-05-09 # Formatted by publCIF

;
_cell_angle_alpha                90.0
_cell_angle_beta                 111.963(13)
_cell_angle_gamma                90.0
_cell_formula_units_Z            4
_cell_length_a                   10.1193(13)
_cell_length_b                   29.068(2)
_cell_length_c                   10.5161(10)
_cell_measurement_reflns_used    4340
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      73.9740
_cell_measurement_theta_min      4.8010
_cell_volume                     2868.8(6)
_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 0.978
_diffrn_measured_fraction_theta_max 0.939
_diffrn_measurement_details
;
  1 omega -109.00  -12.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.5000  -77.0000  -30.0000 97

  2 omega  -50.00   25.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.5000   38.0000  -60.0000 75

  3 omega   25.00  104.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      106.7686  -94.0000  -60.0000 79

  4 omega   66.00  172.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      106.7686   15.0000  -90.0000 106

  5 omega   44.00  108.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      106.7686  -94.0000    0.0000 64

  6 omega   83.00  133.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      106.7686   45.0000 -180.0000 50

  7 omega   35.00   82.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      106.7686  -45.0000   90.0000 47
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.1533528000
_diffrn_orient_matrix_UB_12      -0.0022933000
_diffrn_orient_matrix_UB_13      0.0029216000
_diffrn_orient_matrix_UB_21      0.0584290000
_diffrn_orient_matrix_UB_22      0.0141543000
_diffrn_orient_matrix_UB_23      0.1519996000
_diffrn_orient_matrix_UB_31      0.0095909000
_diffrn_orient_matrix_UB_32      -0.0510905000
_diffrn_orient_matrix_UB_33      0.0416885000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0204
_diffrn_reflns_av_unetI/netI     0.0343
_diffrn_reflns_Laue_measured_fraction_full 0.978
_diffrn_reflns_Laue_measured_fraction_max 0.939
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       35
_diffrn_reflns_limit_k_min       -34
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            9427
_diffrn_reflns_point_group_measured_fraction_full 0.978
_diffrn_reflns_point_group_measured_fraction_max 0.939
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.272
_diffrn_reflns_theta_min         4.712
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.556
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78162
_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.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.180
_exptl_crystal_description
;
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_exptl_crystal_F_000             1080
_exptl_crystal_size_max          .24
_exptl_crystal_size_mid          .20
_exptl_crystal_size_min          .05
_refine_diff_density_max         0.158
_refine_diff_density_min         -0.231
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     359
_refine_ls_number_reflns         5501
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0599
_refine_ls_R_factor_gt           0.0516
_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^)+(0.0832P)^2^+0.3564P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1391
_refine_ls_wR_factor_ref         0.1493
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4588
_reflns_number_total             5501
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo5b01564_si_004.cif
_cod_data_source_block           jcc1206f1
_cod_original_cell_volume        2868.8(5)
_cod_database_code               4036327
_shelxl_version_number           2013-4
_reflns_odcompleteness_completeness 97.74
_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 N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Fixed occupancy and ADP/Uiso:
 H3
2.b Ternary CH refined with riding coordinates:
 C1(H1)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3A), C4(H4), C5(H5), C6(H6), C12(H12), C13(H13), C14(H14), C15(H15),
 C19(H19), C20(H20), C21(H21), C22(H22), C23(H23), C25(H25), C26(H26), C28(H28),
  C29(H29)
2.d Idealised Me refined as rotating group:
 C30(H30A,H30B,H30C), C33(H33A,H33B,H33C), C34(H34A,H34B,H34C), C35(H35A,H35B,
 H35C)
;