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_4034711
_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 O'
_chemical_formula_sum            'C36 H25 N O'
_chemical_formula_weight         487.57
_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             2019-05-15
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                79.071(7)
_cell_angle_beta                 79.762(7)
_cell_angle_gamma                88.940(7)
_cell_formula_units_Z            2
_cell_length_a                   9.7838(9)
_cell_length_b                   10.6982(9)
_cell_length_c                   12.8472(10)
_cell_measurement_reflns_used    2656
_cell_measurement_temperature    297.6(5)
_cell_measurement_theta_max      70.5010
_cell_measurement_theta_min      4.5880
_cell_volume                     1299.1(2)
_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)
;
_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)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      297.6(5)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_details
;
  1 omega  -33.00   55.00   1.0000    2.8600
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -38.0000   90.0000 88

  2 omega   17.00  105.00   1.0000    2.8600
omega____ theta____ kappa____ phi______ frames
    -       36.2921   38.0000   30.0000 88

  3 omega   23.00   90.00   1.0000    2.8600
omega____ theta____ kappa____ phi______ frames
    -       36.2921 -125.0000 -180.0000 67

  4 omega    1.00   75.00   1.0000    2.8600
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -99.0000    0.0000 74

  5 omega  -31.00   63.00   1.0000    2.8600
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -77.0000   60.0000 94

  6 omega   20.00  104.00   1.0000    2.8600
omega____ theta____ kappa____ phi______ frames
    -       36.2921   57.0000    0.0000 84

  7 omega   20.00  104.00   1.0000    2.8600
omega____ theta____ kappa____ phi______ frames
    -       36.2921   57.0000  -90.0000 84

  8 omega   20.00  104.00   1.0000    2.8600
omega____ theta____ kappa____ phi______ frames
    -       36.2921   57.0000 -120.0000 84

  9 omega   10.00  104.00   1.0000    2.8600
omega____ theta____ kappa____ phi______ frames
    -       36.2921   77.0000  -90.0000 94

 10 omega   38.00   91.00   1.0000   11.4200
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -120.0000 53

 11 omega   90.00  175.00   1.0000   11.4200
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000  -30.0000 85

 12 omega   90.00  175.00   1.0000   11.4200
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000 -180.0000 85

 13 omega   40.00  135.00   1.0000   11.4200
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000  150.0000 95

 14 omega   57.00  150.00   1.0000   11.4200
omega____ theta____ kappa____ phi______ frames
    -      108.0000  178.0000 -120.0000 93

 15 omega   90.00  175.00   1.0000   11.4200
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000   60.0000 85

 16 omega   38.00   91.00   1.0000   11.4200
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   30.0000 53

 17 omega   39.00  109.00   1.0000   11.4200
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  -30.0000 70

 18 omega   41.00  126.00   1.0000   11.4200
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -61.0000   30.0000 85

 19 omega   87.00  178.00   1.0000   11.4200
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000  -90.0000 91

 20 omega   38.00  116.00   1.0000   11.4200
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000   60.0000 78

 21 omega   39.00  109.00   1.0000   11.4200
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  -60.0000 70

 22 omega   40.00   98.00   1.0000   11.4200
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  -60.0000 58

 23 omega   38.00   91.00   1.0000   11.4200
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  150.0000 53

 24 omega   38.00  116.00   1.0000   11.4200
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000 -120.0000 78

 25 omega  -31.00   53.00   1.0000    2.8600
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -57.0000 -150.0000 84

 26 omega   20.00  104.00   1.0000    2.8600
omega____ theta____ kappa____ phi______ frames
    -       36.2921   57.0000 -180.0000 84

 27 omega   10.00  104.00   1.0000    2.8600
omega____ theta____ kappa____ phi______ frames
    -       36.2921   77.0000   60.0000 94

 28 omega  -33.00   55.00   1.0000    2.8600
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -38.0000  -90.0000 88

 29 omega   10.00  104.00   1.0000    2.8600
omega____ theta____ kappa____ phi______ frames
    -       36.2921   77.0000    0.0000 94

 30 omega   20.00  104.00   1.0000    2.8600
omega____ theta____ kappa____ phi______ frames
    -       36.2921   57.0000  120.0000 84
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Gemini, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.1270676000
_diffrn_orient_matrix_UB_12      0.0791476000
_diffrn_orient_matrix_UB_13      0.0065969000
_diffrn_orient_matrix_UB_21      -0.0198747000
_diffrn_orient_matrix_UB_22      0.0918287000
_diffrn_orient_matrix_UB_23      -0.1039227000
_diffrn_orient_matrix_UB_31      -0.0952238000
_diffrn_orient_matrix_UB_32      0.0825731000
_diffrn_orient_matrix_UB_33      0.0675073000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0367
_diffrn_reflns_av_unetI/netI     0.0335
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            14341
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.625
_diffrn_reflns_theta_min         4.209
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.574
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.43500
_exptl_absorpt_correction_type   multi-scan
_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'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.246
_exptl_crystal_description       plate
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.140
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     363
_refine_ls_number_reflns         5060
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.1110
_refine_ls_R_factor_gt           0.0796
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0878P)^2^+0.4231P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2072
_refine_ls_wR_factor_ref         0.2315
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3207
_reflns_number_total             5060
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b02339_si_003.cif
_cod_data_source_block           lj-8-1
_cod_database_code               4034711
_shelx_shelxl_version_number     2014/7
_reflns_odcompleteness_completeness 99.96
_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. Uiso/Uaniso restraints and constraints
Uanis(O1) = Uanis(O1A)
Uanis(N2) = Uanis(N2A)
3. Others
 Sof(H20)=Sof(C37)=Sof(H37A)=Sof(H37B)=Sof(H37C)=1-FVAR(1)
 Sof(H22)=Sof(C36)=Sof(H36A)=Sof(H36B)=Sof(H36C)=FVAR(1)
 Sof(O1A)=1-FVAR(2)
 Sof(O1)=FVAR(2)
 Sof(N2A)=1-FVAR(3)
 Sof(N2)=FVAR(3)
4.a Aromatic/amide H refined with riding coordinates:
 C15(H15), C19(H19), C1(H1), C28(H28), C17(H17), C18(H18), C16(H16), C24(H24),
 C34(H34), C20(H20), C27(H27), C25(H25), C26(H26), C2(H2), C5(H5), C22(H22),
 C3(H3), C30(H30), C21(H21), C31(H31), C4(H4), C32(H32), C33(H33)
4.b Idealised Me refined as rotating group:
 C36(H36A,H36B,H36C), C37(H37A,H37B,H37C)
;
_shelx_res_checksum              66145
_shelx_hkl_checksum              86655
_olex2_submission_special_instructions 'No special instructions were received'