Acid-promoted oxidative methylenation of 1,3-dicarbonyl compounds with DMSO: application to the three-component synthesis of Hantzsch-type pyridines
Xue, LuLu; Cheng, Guolin; Zhu, Ruifeng; Cui, Xiuling; RSC Adv. 7 (2017) 44009–; doi:10.1039/C7RA07442E

data_7229148
_publ_section_title
;
 Acid-promoted oxidative methylenation of 1,3-dicarbonyl compounds with
 DMSO: application to the three-component synthesis of Hantzsch-type
 pyridines
;
_journal_issue                   69
_journal_name_full               'RSC Adv.'
_journal_page_first              44009
_journal_paper_doi               10.1039/C7RA07442E
_journal_volume                  7
_journal_year                    2017
_chemical_formula_moiety         'C31 H21 N O2'
_chemical_formula_sum            'C31 H21 N O2'
_chemical_formula_weight         439.49
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_block_doi                 10.5517/ccdc.csd.cc1pcs50
_audit_creation_date             2017-03-31
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Olex2 1.2
(compiled 2017.03.02 svn.r3394 for OlexSys, GUI svn.r5324)
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_audit_update_record
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2017-07-05 deposited with the CCDC.
2017-08-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.0714(14)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.03713(8)
_cell_length_b                   20.9196(3)
_cell_length_c                   18.2183(3)
_cell_measurement_reflns_used    8209
_cell_measurement_temperature    291(2)
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_cell_measurement_theta_min      3.2244
_cell_volume                     2287.96(6)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
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_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
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;
  1 omega   44.00   69.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   57.0000  120.0000 25

  2 omega   -4.00   21.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
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  3 omega  -13.00   14.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   57.0000  120.0000 27

  4 omega -111.00  -21.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000  -61.0000 -120.0000 90

  5 omega  -48.00   25.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000   30.0000 -150.0000 73

  6 omega -115.00  -75.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000  178.0000    0.0000 40

  7 omega -110.00  -44.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
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  8 omega  -40.00  -14.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
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  9 omega  -42.00   22.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000   37.0000  -90.0000 64

 10 omega   -6.00   29.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000   45.0000   30.0000 35

 11 omega  -49.00  -24.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000   45.0000   30.0000 25

 12 omega    6.00   74.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000  -57.0000  -30.0000 68

 13 omega   29.00   94.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000  -99.0000 -150.0000 65

 14 omega   61.00   99.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -94.0000  -30.0000 38

 15 omega  146.00  178.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  111.0000  -30.0000 32

 16 omega  119.00  145.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  111.0000  -30.0000 26

 17 omega   43.00   98.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -45.0000  -30.0000 55

 18 omega   49.00   90.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000  -90.0000 41

 19 omega  104.00  167.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  111.0000  -60.0000 63

 20 omega   95.00  173.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   45.0000   60.0000 78

 21 omega   46.00   98.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -45.0000 -150.0000 52

 22 omega   40.00   90.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000 -120.0000 50

 23 omega   41.00   87.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000  120.0000 46

 24 omega   56.00   90.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000  150.0000 34

 25 omega   42.00  108.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -94.0000    0.0000 66

 26 omega   62.00  116.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -111.0000  150.0000 54

 27 omega   43.00   98.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -45.0000   30.0000 55

 28 omega  121.00  174.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   45.0000 -120.0000 53

 29 omega   69.00   96.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -94.0000   60.0000 27

 30 omega   46.00  108.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -94.0000 -120.0000 62

 31 omega   87.00  173.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   30.0000 -150.0000 86

 32 omega   -4.00   42.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -99.0000  -60.0000 46

 33 omega -113.00  -12.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000  -77.0000 -180.0000 101

 34 omega -111.00  -21.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000  -61.0000    0.0000 90
;
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_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0208
_diffrn_reflns_av_unetI/netI     0.0163
_diffrn_reflns_Laue_measured_fraction_full 1.000
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_diffrn_reflns_theta_max         72.294
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_diffrn_source                   'Enhance (Cu) X-ray Source'
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_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
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_refine_ls_structure_factor_coef Fsqd
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'w=1/[\s^2^(Fo^2^)+(0.0609P)^2^+0.3446P] where P=(Fo^2^+2Fc^2^)/3'
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_reflns_threshold_expression     'I > 2\s(I)'
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_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C20H2O2
_shelx_estimated_absorpt_t_max   0.885
_shelx_estimated_absorpt_t_min   0.875
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C7(H7), C8(H8), C9(H9), C10(H10), C11(H11), C14(H14), C15(H15),
 C16(H16), C17(H17), C18(H18), C21(H21), C22(H22), C23(H23), C24(H24), C25(H25),
  C27(H27), C28(H28), C29(H29), C30(H30), C31(H31)
;
_olex2_submission_special_instructions 'No special instructions were received'