Synthesis of novel imidazole-based triheterocycles via a domino Ugi/Michael reaction and silver-catalyzed heteroannulation
Li, Zhenghua; zhao, yaping; Tian, Guilong; He, Yi; Song, Gonghua; Van Meervelt, Luc; Van der Eycken, Erik V�lery; RSC Adv.  (2016) –; doi:10.1039/C6RA23180B

data_7226936
_publ_section_title
;
 Synthesis of novel imidazole-based triheterocycles via a domino
 Ugi/Michael reaction and silver-catalyzed heteroannulation
;
_journal_name_full               'RSC Adv.'
_journal_paper_doi               10.1039/C6RA23180B
_journal_year                    2016
_chemical_formula_moiety         'C18 H22 N4 O2'
_chemical_formula_sum            'C18 H22 N4 O2'
_chemical_formula_weight         326.39
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2016-01-25
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_audit_update_record
;
2016-08-22 deposited with the CCDC.
2016-10-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 106.774(8)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   14.5377(9)
_cell_length_b                   14.3910(8)
_cell_length_c                   17.5761(15)
_cell_measurement_reflns_used    5623
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      28.9410
_cell_measurement_theta_min      3.4640
_cell_volume                     3520.7(4)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9631
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  1  \w    -75.00  -3.00   1.00   30.00    --  -17.00 126.00  63.00   72
  2  \w    -87.00 -13.00   1.00   30.00    --  -17.00 145.00-129.00   74
  3  \w    -93.00 -35.00   1.00   30.00    --  -17.00-178.00 -60.00   58
  4  \w     -2.00  88.00   1.00   30.00    --   19.03  57.00-150.00   90
  5  \w    -11.00  23.00   1.00   30.00    --   19.03  77.00   0.00   34
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'SuperNova, single source at offset, Eos detector'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0261825000
_diffrn_orient_matrix_UB_12      0.0162417000
_diffrn_orient_matrix_UB_13      0.0381783000
_diffrn_orient_matrix_UB_21      -0.0152013000
_diffrn_orient_matrix_UB_22      -0.0392868000
_diffrn_orient_matrix_UB_23      0.0176556000
_diffrn_orient_matrix_UB_31      0.0409707000
_diffrn_orient_matrix_UB_32      -0.0249290000
_diffrn_orient_matrix_UB_33      -0.0027726000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0193
_diffrn_reflns_av_unetI/netI     0.0205
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            10995
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         2.575
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88886
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.232
_exptl_crystal_description       block
_exptl_crystal_F_000             1392
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: MeOH'
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.274
_refine_diff_density_min         -0.190
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         3595
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.082
_refine_ls_R_factor_all          0.0449
_refine_ls_R_factor_gt           0.0396
_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^)+(0.0316P)^2^+3.8481P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0946
_refine_ls_wR_factor_ref         0.0978
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3192
_reflns_number_total             3595
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6ra23180b2.cif
_cod_data_source_block           ev2005
_cod_original_cell_volume        3520.7(5)
_cod_database_code               7226936
_chemical_oxdiff_formula         'C18 H22 N4 O2'
_chemical_oxdiff_usercomment     'Guilong Tian ZL-1224'
_reflns_odcompleteness_completeness 99.89
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C18(H18)
2.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C19(H19A,H19B), C20(H20A,H20B), C21(H21A,H21B), C22(H22A,
 H22B), C23(H23A,H23B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C8(H8), C9(H9), N17(H17)
2.d X=CH2 refined with riding coordinates:
 C24(H24A,H24B)
2.e Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C)
;
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2016-01-22
_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 1.177
_oxdiff_exptl_absorpt_empirical_full_min 0.889