One-Pot Synthesis of 2,4,5-Trisubstituted Imidazoles via [2 + 2 + 1] Cycloannulation of 1,3-Bishet(aryl)-monothio-1,3-diketones, α-Substituted Methylamines and Sodium Nitrite through α-Nitrosation of Enaminones.
Yugandar, S.; Konda, S.; Parameshwarappa, G.; Ila, H.; The Journal of organic chemistry 81 (2016) 5606–5622; doi:10.1021/acs.joc.6b00938

data_4032007
_publ_section_title
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 One-Pot Synthesis of 2,4,5-Trisubstituted Imidazoles via [2 + 2 + 1]
 Cycloannulation of 1,3-Bishet(aryl)-monothio-1,3-diketones,
 \a-Substituted Methylamines and Sodium Nitrite through \a-Nitrosation of
 Enaminones.
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_journal_issue                   13
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              5606
_journal_page_last               5622
_journal_paper_doi               10.1021/acs.joc.6b00938
_journal_volume                  81
_journal_year                    2016
_chemical_formula_sum            'C21 H19 N3 O3'
_chemical_formula_weight         361.39
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 109.3150(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.4995(4)
_cell_length_b                   11.1353(3)
_cell_length_c                   15.3917(5)
_cell_measurement_reflns_used    16016
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      38.44
_cell_measurement_theta_min      1.88
_cell_volume                     1859.98(10)
_computing_cell_refinement       'SMART APEX II'
_computing_data_collection       'SMART APEX II (Bruker,2010)'
_computing_data_reduction        'SAINT (Bruker,2000)'
_computing_molecular_graphics    'Ortep-3v2 for windows (Farrugia, 1997)'
_computing_publication_material  'PLATON (Spek, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0345
_diffrn_reflns_av_sigmaI/netI    0.0152
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            16016
_diffrn_reflns_theta_full        38.44
_diffrn_reflns_theta_max         38.44
_diffrn_reflns_theta_min         1.88
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  0.3174
_exptl_absorpt_correction_T_min  0.1546
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            gray
_exptl_crystal_density_diffrn    1.291
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.605
_refine_diff_density_min         -0.485
_refine_diff_density_rms         0.162
_refine_ls_extinction_coef       0.052(9)
_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   1.201
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         1369
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.201
_refine_ls_R_factor_all          0.0856
_refine_ls_R_factor_gt           0.0701
_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^)+(0.1593P)^2^+0.8844P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1793
_refine_ls_wR_factor_ref         0.2163
_reflns_number_gt                1251
_reflns_number_total             1369
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            jo6b00938_si_001.cif
_cod_data_source_block           sy517
_cod_depositor_comments
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The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4268 2015-11-12 08:31:59Z antanas 
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_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               4032007