Regioselective Synthesis of Imidazo[1,5-a]quinoxalines and Methyl N-Phenylbenzimidats on Ionic Liquid Support
Chen, Li-Hsun; Kao, Chih-Hsien; DHOLE, SANDIP; Barve, Indrajeet; Shen, Li-Ching; Chung, Wen-Sheng; Sun, Chung-Ming; RSC Adv.  (2016) –; doi:10.1039/C6RA11861E

data_7226176
_publ_section_title
;
 Regioselective Synthesis of Imidazo[1,5-a]quinoxalines and Methyl
 N-Phenylbenzimidats on Ionic Liquid Support
;
_journal_name_full               'RSC Adv.'
_journal_paper_doi               10.1039/C6RA11861E
_journal_year                    2016
_chemical_formula_sum            'C15 H17 N3 O2'
_chemical_formula_weight         271.32
_chemical_name_systematic
'methyl 3,4,4-trimethyl-4,5-dihydroimidazo[1,5-a]quinoxaline-7-carboxylate'
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2016-01-02 deposited with the CCDC.
2016-08-01 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   8.2166(6)
_cell_length_b                   15.0686(10)
_cell_length_c                   22.6298(15)
_cell_measurement_reflns_used    4144
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.2601
_cell_measurement_theta_min      2.8495
_cell_volume                     2801.9(3)
_computing_cell_refinement       'SAINT V7.68A (Bruker AXS, 2009)'
_computing_data_collection       'APEX2 (Bruker AXS, 2010)'
_computing_data_reduction        'SAINT V7.68A (Bruker AXS, 2009)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w 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  0.0454
_diffrn_reflns_av_sigmaI/netI    0.0320
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            19670
_diffrn_reflns_theta_full        26.48
_diffrn_reflns_theta_max         26.48
_diffrn_reflns_theta_min         1.80
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  0.9486
_exptl_absorpt_correction_T_min  0.7938
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.286
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Lump
_exptl_crystal_F_000             1152
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.585
_refine_diff_density_min         -0.581
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     185
_refine_ls_number_reflns         2893
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0585
_refine_ls_R_factor_gt           0.0438
_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^)+(0.0546P)^2^+1.7616P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1096
_refine_ls_wR_factor_ref         0.1185
_reflns_number_gt                2310
_reflns_number_total             2893
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c6ra11861e2.cif
_cod_data_source_block           mo_120560lt_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 4268 2015-11-12 08:31:59Z antanas 
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_cod_database_code               7226176