Copper-Catalyzed Inter/Intramolecular N-Alkenylation of Benzimidazoles via Tandem Processes Involving Selectively Mild Iodination of sp<sup>3</sup> C-H Bond at α-Position of Ester.
Lai, Ting-Ting; Xie, Dan; Zhou, Cheng-He; Cai, Gui-Xin; The Journal of organic chemistry 81 (2016) 8806–8815; doi:10.1021/acs.joc.6b01465

data_4037098
_publ_section_title
;
 Copper-Catalyzed Inter/Intramolecular N-Alkenylation of Benzimidazoles
 via Tandem Processes Involving Selectively Mild Iodination of
 sp<sup>3</sup> C-H Bond at \a-Position of Ester.
;
_journal_issue                   19
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              8806
_journal_page_last               8815
_journal_paper_doi               10.1021/acs.joc.6b01465
_journal_volume                  81
_journal_year                    2016
_chemical_formula_moiety         'C14 H16 N2 O2'
_chemical_formula_sum            'C14 H16 N2 O2'
_chemical_formula_weight         244.28
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2016-01-08
_audit_creation_method
;
Olex2 1.2-alpha
(compiled 2015.09.16 svn.r3215 for OlexSys, GUI svn.r5097)
;
_cell_angle_alpha                91.8992(18)
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_cell_formula_units_Z            4
_cell_length_a                   6.88256(13)
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_cell_length_c                   17.0068(4)
_cell_measurement_reflns_used    12675
_cell_measurement_temperature    286.21(10)
_cell_measurement_theta_max      71.4700
_cell_measurement_theta_min      5.2060
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_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
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Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_environment      air
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;
  1 omega  -32.00   56.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.7203  -38.0000 -180.0000 88

  2 omega   57.00  109.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.7203  178.0000  150.0000 52

  3 omega  -33.00  106.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
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  4 omega   18.00  106.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
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  5 omega    1.00   76.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
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  6 omega    8.00   80.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
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  7 omega    1.00   76.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
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  8 omega   55.00  109.00   1.0000    1.0000
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  9 omega   20.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
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 10 omega   10.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
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 11 omega   40.00   98.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  150.0000 58

 12 omega   38.00   91.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   90.0000 53

 13 omega   39.00  110.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
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 14 omega   38.00   91.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
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 15 omega   38.00  116.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -112.0000 -120.0000 78

 16 omega   40.00  135.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000  150.0000 95

 17 omega   40.00   98.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -150.0000 58

 18 omega   40.00   98.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000   30.0000 58

 19 omega   91.00  176.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000  150.0000 85

 20 omega   40.00   98.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000   60.0000 58

 21 omega   57.00  150.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  178.0000   60.0000 93

 22 omega   40.00   98.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  -30.0000 58

 23 omega   38.00   91.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -90.0000 53

 24 omega   39.00  110.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -95.0000    0.0000 71

 25 omega   39.00  177.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000    0.0000  120.0000 138

 26 omega   10.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.7203   77.0000   60.0000 94

 27 omega   10.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.7203   77.0000 -150.0000 94

 28 omega   10.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.7203   77.0000  120.0000 94

 29 omega   18.00  106.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.7203   38.0000  120.0000 88

 30 omega   10.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.7203   77.0000  -90.0000 94

 31 omega   10.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.7203   77.0000  -60.0000 94

 32 omega  -32.00   56.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.7203  -38.0000  -60.0000 88

 33 omega   87.00  178.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000  -60.0000 91

 34 omega   81.00  176.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000   90.0000 95

 35 omega   81.00  176.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000   30.0000 95

 36 omega   91.00  176.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000    0.0000 85

 37 omega   91.00  176.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000 -180.0000 85

 38 omega   87.00  178.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000  -30.0000 91

 39 omega   70.00  178.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   15.0000  -90.0000 108
;
_diffrn_measurement_device       'four-circle diffractometer'
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_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0265476000
_diffrn_orient_matrix_UB_12      0.1352593000
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_diffrn_orient_matrix_UB_22      -0.0009973000
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_diffrn_orient_matrix_UB_31      0.2237928000
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_diffrn_radiation_monochromator  mirror
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_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0275
_diffrn_reflns_av_unetI/netI     0.0159
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -6
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_diffrn_reflns_number            19081
_diffrn_reflns_point_group_measured_fraction_full 0.999
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_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.553
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_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
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_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
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_exptl_crystal_description       block
_exptl_crystal_F_000             520
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_refine_ls_extinction_method     none
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_refine_ls_R_factor_all          0.0505
_refine_ls_R_factor_gt           0.0483
_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^)+(0.0786P)^2^+0.2015P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1312
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_reflns_number_gt                4710
_reflns_number_total             5083
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_cod_data_source_file            jo6b01465_si_001.cif
_cod_data_source_block           cgx16010701
_cod_depositor_comments
;

2020-04-07
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_moiety     '2(C14 H16 N2 O2)'
_cod_original_formula_sum        'C28 H32 N4 O4'
_cod_original_formula_units_Z    2
_cod_original_formula_weight     488.57
_cod_database_code               4037098
_chemical_oxdiff_formula         'C1 H1 O1 N1'
_reflns_odcompleteness_completeness 99.85
_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 C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C13(H13A,H13B), C15(H15A,H15B), C16(H16A,H16B), C17(H17A,H17B),
 C1A(H1AB,H1AC)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C0AA(H0AA), C1AA(H1AA), C9(H9), C5(H5), C11(H11), C6(H6), C8(H8),
 C3AA(H3AA), C2AA(H2AA), C12(H12), C22(H22), C18(H18), C19(H19)
2.c Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C1B(H1BA,H1BB,H1BC)
;
_shelx_res_checksum              20202
_shelx_hkl_checksum              6128
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2016-01-07
_olex2_submission_special_instructions 'No special instructions were received'