Two-step one-pot synthesis of dihydropyrazinones as Xaa-Ser dipeptide isosteres through morpholine acetal rearrangement.
Lenci, Elena; Innocenti, Riccardo; Menchi, Gloria; Faggi, Cristina; Trabocchi, Andrea; Organic & biomolecular chemistry 13 (2015) 7013–7019; doi:10.1039/c5ob00783f

data_7154516
_publ_section_title
;
 Two-step one-pot synthesis of dihydropyrazinones as Xaa-Ser dipeptide
 isosteres through morpholine acetal rearrangement.
;
_journal_issue                   25
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              7013
_journal_page_last               7019
_journal_paper_doi               10.1039/c5ob00783f
_journal_volume                  13
_journal_year                    2015
_chemical_formula_moiety         'C26 H28 N2 O6'
_chemical_formula_sum            'C26 H28 N2 O6'
_chemical_formula_weight         464.50
_chemical_name_systematic
'R)-(9H-fluoren-9-yl)methyl 4-((R)-3-hydroxy-1-methoxy-1-oxopropan-2-yl)-2-isopropyl-3-oxo-3,4-dihydropyrazine-1-(2H)-carboxylate'
_space_group_IT_number           19
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'Mon Feb 13 13:24:32 2012'
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CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
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_audit_update_record
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2015-04-14 deposited with the CCDC.
2015-05-18 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
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_computing_cell_refinement
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CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
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_computing_data_collection
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CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
(compiled Oct 25 2010,18:11:34)
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_computing_data_reduction
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CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
(compiled Oct 25 2010,18:11:34)
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_computing_molecular_graphics    Ortep3
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_computing_structure_solution    'SIR2004 J.Appl.Cryst.38,381-388'
_diffrn_ambient_temperature      293(2)
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;
  1 omega  -64.00   28.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -46.4074   87.0000 -141.0000 92

  2 omega   24.00   50.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      100.0000  -87.0000  -79.0000 26

  3 omega -110.00  -76.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -46.4074 -125.0000 -150.0000 34

  4 omega  -68.00  -28.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -90.0000   45.0000 -150.0000 40

  5 omega   64.00  173.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      100.0000   15.0000   90.0000 109

  6 omega   38.00   77.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      100.0000  -45.0000   60.0000 39

  7 omega   86.00  133.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      100.0000  -87.0000  -79.0000 47

  8 omega -118.00  -42.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -46.4074  -77.0000  -90.0000 76
;
_diffrn_measurement_device_type  'Xcalibur, Onyx'
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_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Cu) X-ray Source'
_diffrn_radiation_type           CuK\a
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_diffrn_reflns_limit_l_min       -31
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_diffrn_reflns_theta_min         4.61
_diffrn_standards_decay_%        50
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_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.739
_exptl_absorpt_correction_T_max  0.9781
_exptl_absorpt_correction_T_min  0.9531
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CrysAlisPro, Oxford Diffraction Ltd.,
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(compiled Oct 25 2010,18:11:34)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.260
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             984
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
_refine_diff_density_max         1.043
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_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_extinction_coef       0.018(3)
_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   1.176
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
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_refine_ls_number_reflns         4172
_refine_ls_number_restraints     0
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_refine_ls_R_factor_all          0.1352
_refine_ls_R_factor_gt           0.1080
_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^)+(0.2000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2858
_refine_ls_wR_factor_ref         0.3385
_reflns_number_gt                2662
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_cod_data_source_file            c5ob00783f2.cif
_cod_data_source_block           exp_631
_cod_depositor_comments
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The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/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 3271 2015-04-21 07:52:19Z andrius 

 Adding full bibliography for 7154516.cif.
;
_cod_original_sg_symbol_H-M      P212121
_cod_database_code               7154516