Synergistic Acid-Catalyzed Synthesis of N-Aryl-Substituted Azacycles from Anilines and Cyclic Ethers.
Zhang, Zhenbei; Miao, Chengxia; Xia, Chungu; Sun, Wei; Organic letters 18 (2016) 1522–1525; doi:10.1021/acs.orglett.6b00157

data_1543017
_publ_section_title
;
 Synergistic Acid-Catalyzed Synthesis of N-Aryl-Substituted Azacycles from
 Anilines and Cyclic Ethers.
;
_journal_issue                   7
_journal_name_full               'Organic letters'
_journal_page_first              1522
_journal_page_last               1525
_journal_paper_doi               10.1021/acs.orglett.6b00157
_journal_volume                  18
_journal_year                    2016
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C24 H7 B F15 N'
_chemical_formula_sum            'C24 H7 B F15 N'
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_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
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Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
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_cell_measurement_reflns_used    2746
_cell_measurement_temperature    173.00(10)
_cell_measurement_theta_max      25.5430
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_cell_volume                     2197.89(14)
_computing_cell_refinement
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
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CrysAlisPro, Agilent Technologies,
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_diffrn_ambient_environment      N~2~
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_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details
;
  1 omega  -14.00   11.20   1.2000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.1479  -99.0000  150.0000 21

  2 omega  -34.00   18.80   1.2000    3.0000
omega____ theta____ kappa____ phi______ frames
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  3 omega    5.00   77.00   1.2000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       20.7416   57.0000  -90.0000 60

  4 omega  -13.00   13.40   1.2000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.1479   57.0000 -180.0000 22

  5 omega  -60.00   12.00   1.2000    3.0000
omega____ theta____ kappa____ phi______ frames
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  6 omega   16.00   50.80   1.2000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       20.5854  -99.0000   90.0000 29
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_diffrn_orient_matrix_UB_33      0.0072280000
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_diffrn_reflns_theta_max         26.006
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_diffrn_source                   'SuperNova (Mo) X-ray Source'
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
Empirical absorption correction using spherical harmonics,
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_exptl_crystal_colour            'clear light brown'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
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_exptl_crystal_F_000             1192
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 Flack x determined using 1297 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
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_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0539
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_refine_ls_structure_factor_coef Fsqd
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;
 w=1/[\s^2^(Fo^2^)+(0.0270P)^2^]
 where P=(Fo^2^+2Fc^2^)/3
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_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 N1(H1A,H1B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6)
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_olex2_submission_special_instructions 'No special instructions were received'