Facile Synthesis of π-Conjugated Quinazoline-Substituted Ethenes from 2-Ethynylanilines and Benzonitriles under Transition-Metal-Free Conditions.
Wang, Xu; Li, Jiawei; Huang, Yubing; Zhu, Jiayi; Hu, Rongrong; Wu, Wanqing; Jiang, Huanfeng; The Journal of organic chemistry 83 (2018) 10453–10464; doi:10.1021/acs.joc.8b01494

data_4035119
_publ_section_title
;
 Facile Synthesis of \p-Conjugated Quinazoline-Substituted Ethenes from
 2-Ethynylanilines and Benzonitriles under Transition-Metal-Free
 Conditions.
;
_journal_issue                   17
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              10453
_journal_page_last               10464
_journal_paper_doi               10.1021/acs.joc.8b01494
_journal_volume                  83
_journal_year                    2018
_chemical_formula_moiety         'C46 H30 F6 N4 O2'
_chemical_formula_sum            'C46 H30 F6 N4 O2'
_chemical_formula_weight         784.74
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2017-06-22
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_cell_angle_alpha                90
_cell_angle_beta                 108.176(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.9060(2)
_cell_length_b                   16.6094(2)
_cell_length_c                   16.5593(2)
_cell_measurement_reflns_used    7306
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.3820
_cell_measurement_theta_min      4.4910
_cell_volume                     3633.86(9)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (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_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.958
_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     12.00  54.00   1.00    1.00    --   40.46  57.00 -30.00   42
  2  \w     78.00 178.00   1.00    1.50    --  107.48  61.00-120.00  100
  3  \w    102.00 142.00   1.00    1.50    --  107.48 111.00 -30.00   40
  4  \w     82.00 175.00   1.00    1.50    --  107.48  45.00 150.00   93
  5  \w     80.00 105.00   1.00    1.50    --  107.48 -94.00  60.00   25
  6  \w     56.00 139.00   1.00    1.50    --  107.48 -77.00  90.00   83
  7  \w     43.00 121.00   1.00    1.50    --  107.48 -45.00 -30.00   78
  8  \w     23.00  90.00   1.00    1.50    --  107.48 -94.00 -60.00   67
  9  \w    -58.00  31.00   1.00    1.00    --  -40.46  37.00-120.00   89
 10  \w    -89.00 -40.00   1.00    1.00    --  -40.46 -19.00  30.00   49
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0939824000
_diffrn_orient_matrix_UB_12      0.0050766000
_diffrn_orient_matrix_UB_13      -0.0301315000
_diffrn_orient_matrix_UB_21      -0.0531900000
_diffrn_orient_matrix_UB_22      -0.0530578000
_diffrn_orient_matrix_UB_23      -0.0771887000
_diffrn_orient_matrix_UB_31      -0.0437906000
_diffrn_orient_matrix_UB_32      0.0760316000
_diffrn_orient_matrix_UB_33      -0.0520677000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0248
_diffrn_reflns_av_unetI/netI     0.0305
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.958
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            14276
_diffrn_reflns_point_group_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.958
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.667
_diffrn_reflns_theta_min         3.636
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.929
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77464
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.434
_exptl_crystal_description       block
_exptl_crystal_F_000             1616
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.400
_refine_diff_density_min         -0.230
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     525
_refine_ls_number_reflns         7031
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0522
_refine_ls_R_factor_gt           0.0439
_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^)+(0.0645P)^2^+1.2234P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1161
_refine_ls_wR_factor_ref         0.1248
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5985
_reflns_number_total             7031
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b01494_si_003.cif
_cod_data_source_block           exp_684
_cod_database_code               4035119
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.897
_shelx_estimated_absorpt_t_min   0.851
_reflns_odcompleteness_completeness 97.87
_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:
 C3'(H3'), C7'(H7'), C22(H22), C19(H19), C4(H4), C11'(H11'), C4'(H4'), C3(H3),
 C21(H21), C18(H18), C6'(H6'), C14'(H14'), C14(H14), C22'(H22'), C11(H11),
 C13(H13), C12'(H12'), C18'(H18'), C13'(H13'), C19'(H19'), C21'(H21'), C12(H12),
  C7(H7), C6(H6)
2.b Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C8'(H8'A,H8'B,H8'C)
;
_shelx_res_checksum              5489
_shelx_hkl_checksum              77057
_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 1.464
_oxdiff_exptl_absorpt_empirical_full_min 0.747