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_4034710
_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         'C25 H19 N O'
_chemical_formula_sum            'C25 H19 N O'
_chemical_formula_weight         349.41
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-05-30
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 93.86(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   24.706(10)
_cell_length_b                   8.715(2)
_cell_length_c                   4.1298(10)
_cell_measurement_reflns_used    404
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.7500
_cell_measurement_theta_min      4.6780
_cell_volume                     887.2(5)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_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_temperature      293.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0874
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.977
_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      1.00  28.00   0.50   27.50    --  -14.97  19.00-120.00   54
  2  \w    -12.00  18.00   0.50   27.50    --  -14.97 -99.00  30.00   60
  3  \w    -17.00  34.00   0.50   27.50    --   17.08 -57.00-120.00  102
  4  \w    -12.00  85.00   0.50   27.50    --   17.08  19.00 120.00  194
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0026744000
_diffrn_orient_matrix_UB_12      0.0812891000
_diffrn_orient_matrix_UB_13      0.0042064000
_diffrn_orient_matrix_UB_21      -0.0286206000
_diffrn_orient_matrix_UB_22      0.0076594000
_diffrn_orient_matrix_UB_23      -0.0029279000
_diffrn_orient_matrix_UB_31      0.0013512000
_diffrn_orient_matrix_UB_32      -0.0013354000
_diffrn_orient_matrix_UB_33      0.1715025000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0479
_diffrn_reflns_av_unetI/netI     0.0444
_diffrn_reflns_Laue_measured_fraction_full 0.978
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       4
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_number            1781
_diffrn_reflns_point_group_measured_fraction_full 0.646
_diffrn_reflns_point_group_measured_fraction_max 0.641
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.370
_diffrn_reflns_theta_min         3.306
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.14374
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.308
_exptl_crystal_description       block
_exptl_crystal_F_000             368
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.378
_refine_diff_density_min         -0.441
_refine_diff_density_rms         0.095
_refine_ls_abs_structure_details
;
 Flack x determined using 159 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -7.9(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     134
_refine_ls_number_reflns         1161
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.090
_refine_ls_R_factor_all          0.1008
_refine_ls_R_factor_gt           0.0928
_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^)+(0.1927P)^2^+0.1352P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2498
_refine_ls_wR_factor_ref         0.2722
_reflns_Friedel_coverage         0.229
_reflns_Friedel_fraction_full    0.266
_reflns_Friedel_fraction_max     0.256
_reflns_number_gt                966
_reflns_number_total             1161
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b02339_si_004.cif
_cod_data_source_block           190530_s1_lj
_cod_database_code               4034710
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         c12h12n2o3
_shelx_estimated_absorpt_t_max   0.980
_shelx_estimated_absorpt_t_min   0.973
_reflns_odcompleteness_completeness 97.73
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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. Others
 Fixed Sof: O1(0.5) N1(0.5)
3.a Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C9(H9), C10(H10), C11(H11), C13(H13), C14(H14)
3.b Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C)
;
_shelx_res_checksum              27980
_shelx_hkl_checksum              68727
_olex2_date_sample_data_collection 2009-06-28
_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
;
_oxdiff_exptl_absorpt_empirical_full_max 2.870
_oxdiff_exptl_absorpt_empirical_full_min 0.494