Copper-catalyzed oxidative coupling reaction of α,β-unsaturated aldehydes with amidines: synthesis of 1,2,4-trisubstituted-1H-imidazole-5-carbaldehydes
Li, Yaxuan; Fu, Yajie; Ren, Chaojie; Tang, Dong; Wu, Ping; Meng, Xu; Chen, Baohua; Organic Chemistry Frontiers 2 (2015) 1632–; doi:10.1039/C5QO00285K

data_1553187
_publ_section_title
;
 Copper-catalyzed oxidative coupling reaction of \a,\b-unsaturated
 aldehydes with amidines: synthesis of
 1,2,4-trisubstituted-1H-imidazole-5-carbaldehydes
;
_journal_issue                   12
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              1632
_journal_paper_doi               10.1039/C5QO00285K
_journal_volume                  2
_journal_year                    2015
_chemical_formula_moiety         'C22 H16 N2 O'
_chemical_formula_sum            'C22 H16 N2 O'
_chemical_formula_weight         324.37
_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
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2015-03-24
_audit_creation_method
;
Olex2 1.2
(compiled 2014.11.28 svn.r3106 for OlexSys, GUI svn.r4959)
;
_audit_update_record
;
2015-06-29 deposited with the CCDC.
2015-11-04 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 100.439(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.4582(5)
_cell_length_b                   11.1421(5)
_cell_length_c                   18.5214(12)
_cell_measurement_reflns_used    1570
_cell_measurement_temperature    291.73(10)
_cell_measurement_theta_max      24.2740
_cell_measurement_theta_min      3.8140
_cell_volume                     1716.61(17)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      291.73(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
  1 omega  -12.00   84.00   1.5000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       20.7416   19.0000  150.0000 64

  2 omega  -27.00    0.00   1.5000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.3041   38.0000  -60.0000 18

  3 omega  -32.00   40.00   1.5000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       20.7416  -57.0000  -60.0000 48

  4 omega   46.00   73.00   1.5000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       20.7416  178.0000  120.0000 18
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0742174000
_diffrn_orient_matrix_UB_12      -0.0252359000
_diffrn_orient_matrix_UB_13      -0.0173262000
_diffrn_orient_matrix_UB_21      0.0047710000
_diffrn_orient_matrix_UB_22      -0.0425630000
_diffrn_orient_matrix_UB_23      0.0287886000
_diffrn_orient_matrix_UB_31      -0.0416143000
_diffrn_orient_matrix_UB_32      0.0400645000
_diffrn_orient_matrix_UB_33      0.0197211000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0290
_diffrn_reflns_av_unetI/netI     0.0484
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            6540
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         3.52
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87831
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.255
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.32
_refine_diff_density_max         0.342
_refine_diff_density_min         -0.233
_refine_diff_density_rms         0.036
_refine_ls_extinction_coef       0.027(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3377
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0863
_refine_ls_R_factor_gt           0.0557
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0445P)^2^+0.5478P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1205
_refine_ls_wR_factor_ref         0.1413
_reflns_number_gt                2316
_reflns_number_total             3377
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5qo00285k2.cif
_cod_data_source_block           liyx0323
_cod_original_cell_volume        1716.59(17)
_cod_database_code               1553187
_reflns_odcompleteness_completeness 99.65
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C14(H14), C5(H5), C13(H13), C1(H1), C22(H22), C16(H16), C10(H10), C18(H18),
 C3(H3), C11(H11), C12(H12), C21(H21), C2(H2), C4(H4), C20(H20), C19(H19)
;
_olex2_date_sample_data_collection 2015-03-23
_olex2_submission_special_instructions 'No special instructions were received'