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_4034709
_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         'C43 H35 N O5'
_chemical_formula_sum            'C43 H36 N O5'
_chemical_formula_weight         646.73
_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'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2019-06-22
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 93.8350(12)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.08424(9)
_cell_length_b                   18.4274(2)
_cell_length_c                   28.6542(4)
_cell_measurement_reflns_used    5914
_cell_measurement_temperature    297.2(5)
_cell_measurement_theta_max      71.6690
_cell_measurement_theta_min      4.7710
_cell_volume                     3205.42(7)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_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      297.2(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
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
--------------------------------------------------------------------------
  1  \w   -106.00  33.00   1.00    3.85    --  -36.54   0.00-180.00  139
  2  \w     23.00  90.00   1.00    3.85    --   36.54-125.00 150.00   67
  3  \w     23.00  90.00   1.00    3.85    --   36.54-125.00 -60.00   67
  4  \w     20.00 104.00   1.00    3.85    --   36.54  57.00-180.00   84
  5  \w     88.00 173.00   1.00   15.39    --  106.21  61.00-120.00   85
  6  \w     36.00 128.00   1.00   15.39    --  106.21 -30.00-150.00   92
  7  \w     39.00 124.00   1.00   15.39    --  106.21 -61.00 150.00   85
  8  \w     37.00 109.00   1.00   15.39    --  106.21 -94.00 120.00   72
  9  \w     38.00 124.00   1.00   15.39    --  106.21 -45.00  90.00   86
 10  \w     85.00 176.00   1.00   15.39    --  106.21  30.00 -30.00   91
 11  \w     37.00 109.00   1.00   15.39    --  106.21 -94.00  60.00   72
 12  \w    100.00 176.00   1.00   15.39    --  106.21 111.00 120.00   76
 13  \w   -106.00 -18.00   1.00    3.85    --  -36.54 -38.00  30.00   88
 14  \w     10.00 104.00   1.00    3.85    --   36.54  77.00   0.00   94
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Gemini, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0318366000
_diffrn_orient_matrix_UB_12      -0.0198761000
_diffrn_orient_matrix_UB_13      -0.0522287000
_diffrn_orient_matrix_UB_21      0.1978402000
_diffrn_orient_matrix_UB_22      -0.0521739000
_diffrn_orient_matrix_UB_23      0.0056388000
_diffrn_orient_matrix_UB_31      -0.1556752000
_diffrn_orient_matrix_UB_32      -0.0622450000
_diffrn_orient_matrix_UB_33      0.0119769000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0359
_diffrn_reflns_av_unetI/netI     0.0324
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            17880
_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         71.932
_diffrn_reflns_theta_min         3.914
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.697
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.27545
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.340
_exptl_crystal_description       block
_exptl_crystal_F_000             1364
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.660
_refine_diff_density_min         -0.373
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     452
_refine_ls_number_reflns         6188
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0814
_refine_ls_R_factor_gt           0.0709
_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^)+(0.1320P)^2^+1.3210P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2067
_refine_ls_wR_factor_ref         0.2211
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5061
_reflns_number_total             6188
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b02339_si_005.cif
_cod_data_source_block           lj-a56-2
_cod_database_code               4034709
_shelx_shelxl_version_number     2014/7
_reflns_odcompleteness_completeness 99.90
_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:
 C00N(H00N), C00O(H00O), C00S(H00S), C00V(H00V), C00W(H00W), C00X(H00X),
 C00Y(H00Y), C010(H010), C011(H011), C012(H012), C014(H014), C015(H015),
 C016(H016)
2.b Idealised Me refined as rotating group:
 C017(H01A,H01B,H01C), C018(H01D,H01E,H01F), C019(H01G,H01H,H01I), C01A(H01J,
 H01K,H01L), C01B(H01M,H01N,H01O), C01C(H01P,H01Q,H01R), C01D(H01S,H01T,H01U)
;
_olex2_date_sample_data_collection 2019-06-21
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.942
_oxdiff_exptl_absorpt_empirical_full_min 0.731