Chemoselective syntheses of spirodihydrofuryl and spirocyclopropyl barbiturates via cascade reactions of barbiturate-based olefins and acetylacetone.
Yan, Xuebin; Shao, Pei; Song, Xixi; Zhang, Chaofei; Lu, Chang; Liu, Songtao; Li, Yanli; Organic & biomolecular chemistry 17 (2019) 2684–2690; doi:10.1039/c9ob00004f

data_7156679
_publ_section_title
;
 Chemoselective syntheses of spirodihydrofuryl and spirocyclopropyl
 barbiturates via cascade reactions of barbiturate-based olefins and
 acetylacetone.
;
_journal_issue                   10
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              2684
_journal_page_last               2690
_journal_paper_doi               10.1039/c9ob00004f
_journal_volume                  17
_journal_year                    2019
_chemical_formula_moiety         'C18 H17 Cl N2 O5'
_chemical_formula_sum            'C18 H17 Cl N2 O5'
_chemical_formula_weight         376.78
_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_creation_date             2018-12-03
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
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_cell_formula_units_Z            4
_cell_length_a                   9.7345(3)
_cell_length_b                   14.0642(4)
_cell_length_c                   13.0475(4)
_cell_measurement_reflns_used    4199
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.7240
_cell_measurement_theta_min      4.5410
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_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
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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)'
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;
  1 omega  -62.00   20.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
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  2 omega   12.00   37.00   1.0000    1.0000
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  3 omega  -65.00  -15.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
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  4 omega  -38.00   -3.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
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  5 omega  -35.00    4.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
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  6 omega   41.00   66.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
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  7 omega   38.00  105.00   1.0000    1.0000
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  8 omega   30.00   55.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
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  9 omega  -31.00    2.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
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 10 omega   14.00   87.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
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 11 omega  -18.00   50.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -37.0000 -150.0000 68

 12 omega   60.00   86.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000 -120.0000 26

 13 omega   70.00  109.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000 -150.0000 39

 14 omega   -4.00   74.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -99.0000   60.0000 78

 15 omega   68.00   98.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000   30.0000 30

 16 omega   16.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   19.0000 -150.0000 88

 17 omega    2.00   31.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -99.0000  -30.0000 29

 18 omega   40.00   71.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734 -107.0000 -139.0000 31

 19 omega   47.00   91.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000    0.0000 44

 20 omega  146.00  177.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
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 21 omega   96.00  135.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000    0.0000 39

 22 omega   51.00  107.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  -30.0000 56

 23 omega  137.00  162.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000   60.0000 25

 24 omega  102.00  177.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000   30.0000 75

 25 omega   38.00   92.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  -60.0000 54

 26 omega   88.00  117.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000   60.0000 29

 27 omega   39.00  115.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000 -180.0000 76

 28 omega   94.00  173.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000  -60.0000 79

 29 omega   57.00  145.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  178.0000 -150.0000 88

 30 omega   79.00  105.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -90.0000 26

 31 omega   42.00   86.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -120.0000 44

 32 omega   94.00  134.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000   90.0000 40

 33 omega  136.00  162.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -90.0000 26

 34 omega   38.00  109.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000 -120.0000 71

 35 omega   46.00   99.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -150.0000 53

 36 omega  115.00  170.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  107.0000  -41.0000 55
;
_diffrn_measurement_device       'four-circle diffractometer'
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_diffrn_radiation_monochromator  graphite
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_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0334
_diffrn_reflns_av_unetI/netI     0.0271
_diffrn_reflns_Laue_measured_fraction_full 1.000
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_diffrn_reflns_limit_h_min       -11
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_diffrn_reflns_theta_min         4.624
_diffrn_source                   'Enhance (Cu) X-ray Source'
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_exptl_absorpt_correction_T_min  0.80793
_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_colour            colourless
_exptl_crystal_colour_primary    colourless
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_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.1
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_refine_ls_extinction_coef       0.0069(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
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_refine_ls_number_restraints     0
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_refine_ls_R_factor_all          0.0587
_refine_ls_R_factor_gt           0.0484
_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^)+(0.0846P)^2^+0.6545P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
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_reflns_number_gt                2630
_reflns_number_total             3190
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9ob00004f3.cif
_cod_data_source_block           201811442
_cod_depositor_comments          'Adding full bibliography for 7156679.cif.'
_cod_original_cell_volume        1785.39(10)
_cod_database_code               7156679
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C15H15O3N2Cl1
_shelx_estimated_absorpt_t_max   0.811
_shelx_estimated_absorpt_t_min   0.682
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C6(H6)
2.b Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9), C11(H11), C12(H12)
2.c Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C16(H16A,H16B,H16C), C17(H17A,H17B,H17C), C18(H18A,H18B,
 H18C)
;
_olex2_submission_special_instructions 'No special instructions were received'