Direct Construction of 2-Aryliminochromenes from Arynes, N,S-Keteneacetals, and DMF.
Wen, Li-Rong; Man, Ning-Ning; Yuan, Wen-Kui; Li, Ming; The Journal of organic chemistry 81 (2016) 5942–5948; doi:10.1021/acs.joc.6b00843

data_4036893
_publ_section_title
;
 Direct Construction of 2-Aryliminochromenes from Arynes,
 N,S-Keteneacetals, and DMF.
;
_journal_issue                   14
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              5942
_journal_page_last               5948
_journal_paper_doi               10.1021/acs.joc.6b00843
_journal_volume                  81
_journal_year                    2016
_chemical_formula_moiety         'C22 H15 N O2'
_chemical_formula_sum            'C22 H15 N O2'
_chemical_formula_weight         325.35
_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   geom
_audit_creation_date             2014-07-09
_audit_creation_method
;
Olex2 1.2
(compiled 2013.12.10 svn.r2850 for OlexSys, GUI svn.r4736)
;
_cell_angle_alpha                90
_cell_angle_beta                 105.311(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   18.476(3)
_cell_length_b                   10.9715(15)
_cell_length_c                   16.715(3)
_cell_measurement_reflns_used    9700
_cell_measurement_temperature    173.1500
_cell_measurement_theta_max      27.4845
_cell_measurement_theta_min      1.1427
_cell_volume                     3268.0(9)
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2013)'
_computing_structure_solution
;
'SHELXS (Sheldrick, 2013)'
;
_diffrn_ambient_temperature      173.1500
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device
;
Saturn724+ (2x2 bin mode)
;
_diffrn_measurement_device_details
;
AFC10: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  'MM007-HF CCD(Saturn 724+)'
_diffrn_measurement_method       '\w scans at fixed \c = 45\%'
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      0.0464
_diffrn_orient_matrix_UB_12      0.0281
_diffrn_orient_matrix_UB_13      -0.0301
_diffrn_orient_matrix_UB_21      0.0603
_diffrn_orient_matrix_UB_22      -0.0409
_diffrn_orient_matrix_UB_23      0.0548
_diffrn_orient_matrix_UB_31      0.0140
_diffrn_orient_matrix_UB_32      -0.0350
_diffrn_orient_matrix_UB_33      -0.0416
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0376
_diffrn_reflns_av_unetI/netI     0.0292
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            26137
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.494
_diffrn_reflns_theta_min         1.143
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           24.0000
_diffrn_source_power             1.2000
_diffrn_source_voltage           50.0000
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8332
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.322
_exptl_crystal_description       block
_exptl_crystal_F_000             1360
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.352
_refine_diff_density_min         -0.195
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.163
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     451
_refine_ls_number_reflns         7463
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.163
_refine_ls_R_factor_all          0.0706
_refine_ls_R_factor_gt           0.0648
_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^)+(0.0614P)^2^+1.2326P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1514
_refine_ls_wR_factor_ref         0.1556
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6894
_reflns_number_total             7463
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo6b00843_si_001.cif
_cod_data_source_block           a
_cod_original_cell_volume        3268.1(8)
_cod_database_code               4036893
_shelxl_version_number           2013-4
_diffrn_number_total             7864
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3A(H3A), C5A(H5A), C6A(H6A), C7A(H7A), C8A(H8A), C11A(H11A), C12A(H12A),
 C13A(H13A), C14A(H14A), C15A(H15A), C18A(H18A), C19A(H19A), C20A(H20A),
 C21A(H21A), C22A(H22A), C3(H3), C5(H5), C6(H6), C7(H7), C8(H8), C11(H11),
 C12(H12), C13(H13), C14(H14), C15(H15), C18(H18), C19(H19), C20(H20), C21(H21),
  C22(H22)
;
_shelx_res_checksum              81301
_shelx_hkl_checksum              53461