Double ortho-C-H Activation/Annulation of Benzamides with Aryl Alkynes: A Route to Double-Helical Polycyclic Heteroaromatics.
Li, Jian; Liu, Junjie; Yin, Jiangliang; Zhang, Yuming; Han, Weiguo; Lan, Jingbo; Wu, Di; Bin, Zhengyang; You, Jingsong; The Journal of organic chemistry  (2019) –; doi:10.1021/acs.joc.9b02339

data_4034712
_publ_section_title
;
 Double ortho-C-H Activation/Annulation of Benzamides with Aryl Alkynes: A
 Route to Double-Helical Polycyclic Heteroaromatics.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.9b02339
_journal_year                    2019
_chemical_formula_moiety         'C36 H25 N O2'
_chemical_formula_sum            'C36 H25 N O2'
_chemical_formula_weight         503.57
_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
_atom_sites_solution_primary     direct
_audit_creation_date             2019-01-08
_audit_creation_method
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Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
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_cell_formula_units_Z            2
_cell_length_a                   9.7491(5)
_cell_length_b                   10.3104(5)
_cell_length_c                   13.5196(7)
_cell_measurement_reflns_used    4766
_cell_measurement_temperature    291.16(10)
_cell_measurement_theta_max      72.0250
_cell_measurement_theta_min      5.1110
_cell_volume                     1280.57(12)
_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
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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_data_reduction
;
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)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
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_diffrn_ambient_environment      air
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_diffrn_detector                 'CCD plate'
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_diffrn_measurement_details
;
  1 omega   20.00  104.00   1.0000    2.2100
omega____ theta____ kappa____ phi______ frames
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  2 omega  -31.00   53.00   1.0000    2.2100
omega____ theta____ kappa____ phi______ frames
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  3 omega   20.00  104.00   1.0000    2.2100
omega____ theta____ kappa____ phi______ frames
    -       36.2921   57.0000  -90.0000 84

  4 omega    1.00   75.00   1.0000    2.2100
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -99.0000  -90.0000 74

  5 omega   17.00  105.00   1.0000    2.2100
omega____ theta____ kappa____ phi______ frames
    -       36.2921   38.0000   90.0000 88

  6 omega   20.00  104.00   1.0000    2.2100
omega____ theta____ kappa____ phi______ frames
    -       36.2921   57.0000 -150.0000 84

  7 omega    1.00   75.00   1.0000    2.2100
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -99.0000  150.0000 74

  8 omega   23.00   90.00   1.0000    2.2100
omega____ theta____ kappa____ phi______ frames
    -       36.2921 -125.0000   60.0000 67

  9 omega  -35.00   66.00   1.0000    2.2100
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -19.0000  -90.0000 101

 10 omega    1.00   75.00   1.0000    2.2100
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -99.0000   90.0000 74

 11 omega   57.00  150.00   1.0000    8.8600
omega____ theta____ kappa____ phi______ frames
    -      108.0000  178.0000 -180.0000 93

 12 omega   39.00  109.00   1.0000    8.8600
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000   60.0000 70

 13 omega   70.00  178.00   1.0000    8.8600
omega____ theta____ kappa____ phi______ frames
    -      108.0000   15.0000 -120.0000 108

 14 omega   39.00  109.00   1.0000    8.8600
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000 -120.0000 70

 15 omega   41.00  126.00   1.0000    8.8600
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -61.0000  150.0000 85

 16 omega   40.00   98.00   1.0000    8.8600
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  -60.0000 58

 17 omega   40.00   98.00   1.0000    8.8600
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000   90.0000 58

 18 omega   40.00   98.00   1.0000    8.8600
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -120.0000 58

 19 omega   38.00   91.00   1.0000    8.8600
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -60.0000 53

 20 omega   38.00   91.00   1.0000    8.8600
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -90.0000 53

 21 omega   39.00  109.00   1.0000    8.8600
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  -30.0000 70

 22 omega   38.00   91.00   1.0000    8.8600
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  120.0000 53

 23 omega   40.00   98.00   1.0000    8.8600
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -180.0000 58

 24 omega   38.00  116.00   1.0000    8.8600
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000 -180.0000 78

 25 omega  100.00  178.00   1.0000    8.8600
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000 -120.0000 78

 26 omega  100.00  178.00   1.0000    8.8600
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000 -180.0000 78

 27 omega   91.00  176.00   1.0000    8.8600
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000  -60.0000 85

 28 omega    0.00   26.00   1.0000    2.2100
omega____ theta____ kappa____ phi______ frames
    -       36.2921   94.0000 -143.9971 26

 29 omega  -35.00   66.00   1.0000    2.2100
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -19.0000   90.0000 101

 30 omega  -33.00   55.00   1.0000    2.2100
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -38.0000   30.0000 88

 31 omega   10.00  104.00   1.0000    2.2100
omega____ theta____ kappa____ phi______ frames
    -       36.2921   77.0000  120.0000 94

 32 omega   10.00  104.00   1.0000    2.2100
omega____ theta____ kappa____ phi______ frames
    -       36.2921   77.0000  -30.0000 94
;
_diffrn_measurement_device       'four-circle diffractometer'
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_diffrn_orient_matrix_UB_31      0.1429349000
_diffrn_orient_matrix_UB_32      0.0265664000
_diffrn_orient_matrix_UB_33      0.0200095000
_diffrn_radiation_monochromator  graphite
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_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
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_diffrn_source                   'Enhance (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 yellowish yellow'
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_exptl_crystal_colour_modifier   yellowish
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_exptl_crystal_description       plate
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.6
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_exptl_crystal_size_min          0.01
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_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1145P)^2^+0.1573P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
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_cod_data_source_block           lj-b28-2-150k
_cod_database_code               4034712
_reflns_odcompleteness_completeness 99.91
_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 Aromatic/amide H refined with riding coordinates:
 C00D(H00D), C00E(H00E), C00F(H00F), C00G(H00G), C00K(H00K), C00L(H00L),
 C00M(H00M), C00N(H00N), C00P(H00P), C00Q(H00Q), C00R(H00R), C00S(H00S),
 C00T(H00T), C00U(H00U), C00V(H00V), C00W(H00W), C00X(H00X), C00Y(H00Y),
 C00Z(H00Z), C010(H010), C011(H011), C012(H012)
2.b Idealised Me refined as rotating group:
 C013(H01A,H01B,H01C)
;
_shelx_res_checksum              87266
_shelx_hkl_checksum              86098
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2019-01-07
_olex2_submission_special_instructions 'No special instructions were received'