Acid-Promoted One-Pot Synthesis of Substituted Furan and 6-Methylpyrazin-2(1 H)-one Derivatives via Allene Intermediate Formed in Situ.
Lei, Jie; Xu, Zhi-Gang; Tang, Dian-Yong; Li, Yong; Xu, Jia; Li, Hong-Yu; Zhu, Jin; Chen, Zhong-Zhu; ACS combinatorial science 20 (2018) 292–297; doi:10.1021/acscombsci.8b00005

data_4515831
_publ_section_title
;
 Acid-Promoted One-Pot Synthesis of Substituted Furan and
 6-Methylpyrazin-2(1 H)-one Derivatives via Allene Intermediate Formed in
 Situ.
;
_journal_issue                   5
_journal_name_full               'ACS combinatorial science'
_journal_page_first              292
_journal_page_last               297
_journal_paper_doi               10.1021/acscombsci.8b00005
_journal_volume                  20
_journal_year                    2018
_chemical_formula_moiety         'C21 H16 N2 O3'
_chemical_formula_sum            'C21 H16 N2 O3'
_chemical_formula_weight         344.36
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2017-04-18
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.6461(3)
_cell_length_b                   9.1906(3)
_cell_length_c                   20.9044(8)
_cell_measurement_reflns_used    1773
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.2260
_cell_measurement_theta_min      3.0520
_cell_volume                     1661.12(10)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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_temperature      293.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0874
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
  1 omega  -20.00   32.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.9669   77.0000   90.0000 52

  2 omega   51.00   77.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       16.6856   77.0000  -30.0000 26

  3 omega   -7.00   50.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       16.6856   77.0000 -150.0000 57
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0778027000
_diffrn_orient_matrix_UB_12      -0.0100996000
_diffrn_orient_matrix_UB_13      -0.0097668000
_diffrn_orient_matrix_UB_21      0.0227991000
_diffrn_orient_matrix_UB_22      -0.0601219000
_diffrn_orient_matrix_UB_23      -0.0190726000
_diffrn_orient_matrix_UB_31      -0.0123640000
_diffrn_orient_matrix_UB_32      -0.0473845000
_diffrn_orient_matrix_UB_33      0.0263013000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0169
_diffrn_reflns_av_unetI/netI     0.0415
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            4829
_diffrn_reflns_point_group_measured_fraction_full 0.924
_diffrn_reflns_point_group_measured_fraction_max 0.913
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         2.951
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.98131
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.377
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description
;
;
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.139
_refine_diff_density_min         -0.201
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details
;
 Flack x determined using 779 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.8(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         3113
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0587
_refine_ls_R_factor_gt           0.0446
_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^)+(0.0442P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0882
_refine_ls_wR_factor_ref         0.0961
_reflns_Friedel_coverage         0.582
_reflns_Friedel_fraction_full    0.820
_reflns_Friedel_fraction_max     0.795
_reflns_number_gt                2560
_reflns_number_total             3113
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            co8b00005_si_002.cif
_cod_data_source_block           170417_s6_lj
_cod_original_cell_volume        1661.11(10)
_cod_database_code               4515831
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         c12h12n2o3
_shelx_estimated_absorpt_t_max   0.982
_shelx_estimated_absorpt_t_min   0.968
_reflns_odcompleteness_completeness 99.70
_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
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C9(H9), C13(H13), C17(H17), C18(H18),
 C19(H19), C20(H20), C21(H21)
2.c Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C)
;
_olex2_submission_special_instructions 'No special instructions were received'