Chemoselective acylation of benzimidazoles with phenylacetic acids under different Cu catalysts to give fused five-membered N-heterocycles or tertiary amides.
Mai, Shaoyu; Zhao, Yingwei; Song, Qiuling; Organic & biomolecular chemistry 14 (2016) 8685–8690; doi:10.1039/c6ob01167e

data_7155206
_publ_section_title
;
 Chemoselective acylation of benzimidazoles with phenylacetic acids under
 different Cu catalysts to give fused five-membered N-heterocycles or
 tertiary amides.
;
_journal_issue                   37
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              8685
_journal_page_last               8690
_journal_paper_doi               10.1039/c6ob01167e
_journal_volume                  14
_journal_year                    2016
_chemical_formula_moiety         'C16 H12 N2 O'
_chemical_formula_sum            'C16 H12 N2 O'
_chemical_formula_weight         248.28
_chemical_name_systematic
7,8-dimethyl-11H-benzo[4,5]imidazo[1,2-a]indol-11-one
_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'
_symmetry_space_group_name_Hall  '-P 2ybc'
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Olex2 1.2
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2016-03-11 deposited with the CCDC.
2016-07-12 downloaded from the CCDC.
;
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Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
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omega____ theta____ kappa____ phi______ frames
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  2 omega    4.00   83.00   1.0000    1.3700
omega____ theta____ kappa____ phi______ frames
    -       18.1991   57.0000  -60.0000 79

  3 omega   60.00   86.00   1.0000    1.3700
omega____ theta____ kappa____ phi______ frames
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omega____ theta____ kappa____ phi______ frames
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  5 omega  -12.00   58.00   1.0000    1.3700
omega____ theta____ kappa____ phi______ frames
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  6 omega   35.00   94.00   1.0000    1.3700
omega____ theta____ kappa____ phi______ frames
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_diffrn_reflns_av_unetI/netI     0.0384
_diffrn_reflns_Laue_measured_fraction_full 0.998
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_diffrn_reflns_theta_min         3.320
_diffrn_source                   'Enhance (Mo) X-ray Source'
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CrysAlisPro, Agilent Technologies,
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Empirical absorption correction using spherical harmonics,
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_exptl_crystal_colour            'light red'
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_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
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'w=1/[\s^2^(Fo^2^)+(0.0524P)^2^+0.1669P] where P=(Fo^2^+2Fc^2^)/3'
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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 Aromatic/amide H refined with riding coordinates:
 C4(H4), C7(H7), C10(H10), C11(H11), C12(H12), C13(H13)
2.b Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C16(H16A,H16B,H16C)
;
_olex2_submission_special_instructions 'No special instructions were received'