Blaise reaction: synthesis, skeletal diversification of C(4) substituted 5-ylidenepyrrol-(5H)-ones and the role of the strategically located ester on the reactivity of the nitriles
Surya Prakash Rao, H.; Padder, Ashiq Hussain; New Journal of Chemistry 44 (2020) 9010–9017; doi:10.1039/D0NJ00231C

data_7059468
_publ_section_title
;
 Blaise reaction: synthesis, skeletal diversification of C(4) substituted
 5-ylidenepyrrol-(5H)-ones and the role of the strategically located ester
 on the reactivity of the nitriles
;
_journal_issue                   21
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              9010
_journal_page_last               9017
_journal_paper_doi               10.1039/D0NJ00231C
_journal_volume                  44
_journal_year                    2020
_chemical_formula_moiety         'C15 H15 N O4'
_chemical_formula_sum            'C15 H15 N O4'
_chemical_formula_weight         273.29
_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_Int_Tables_number      14
_atom_sites_solution_primary     direct
_audit_creation_date             2019-04-25
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Olex2 1.2-ac3
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2019-04-25 deposited with the CCDC.	2020-03-17 downloaded from the CCDC.
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_cell_angle_alpha                90
_cell_angle_beta                 103.083(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
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_cell_length_b                   4.2138(3)
_cell_length_c                   19.6741(12)
_cell_measurement_reflns_used    2238
_cell_measurement_temperature    298
_cell_measurement_theta_max      29.2773
_cell_measurement_theta_min      3.5756
_cell_volume                     1347.79(16)
_computing_cell_refinement
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CrysAlisPro, Agilent Technologies,
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_computing_data_collection
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CrysAlisPro, Agilent Technologies,
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CrysAlisPro, Agilent Technologies,
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_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
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_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      298
_diffrn_detector_area_resol_mean 15.9821
_diffrn_measured_fraction_theta_full 0.9974
_diffrn_measured_fraction_theta_max 0.8155
_diffrn_measurement_details
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  1 omega  -11.00   21.00   1.0000   28.0800
omega____ theta____ kappa____ phi______ frames
    -      -17.0272  -99.0000 -120.0000 32

  2 omega    1.00   88.00   1.0000   28.0800
omega____ theta____ kappa____ phi______ frames
    -       19.8397   37.0000 -150.0000 87

  3 omega   -5.00   92.00   1.0000   28.0800
omega____ theta____ kappa____ phi______ frames
    -       19.8397   37.0000  120.0000 97
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_diffrn_measurement_device_type  'Xcalibur, Eos'
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_diffrn_orient_matrix_UB_31      -0.0009832000
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_diffrn_orient_matrix_UB_33      0.0009128000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0123
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_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            5482
_diffrn_reflns_theta_full        25.0000
_diffrn_reflns_theta_max         29.34
_diffrn_reflns_theta_min         3.64
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87493
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
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Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
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_exptl_crystal_colour            yellow
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_refine_ls_shift/su_mean         0.0002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0505P)^2^+0.2617P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
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_reflns_number_gt                2553
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_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d0nj00231c3.cif
_cod_data_source_block           HSP-AHP-II-85-AS
_cod_depositor_comments
;Adding full bibliography for 7059467--7059468.cif.

 Adding full bibliography for 7059467--7059468.cif.
;
_cod_original_sg_symbol_Hall     '-P 2ybc (x-z,y,z)'
_cod_database_code               7059468
_chemical_oxdiff_formula         'C12 H20 N1 O2'
_chemical_oxdiff_usercomment     'YELLOW COLOUR BLOCK, 298K, 0.86 0.44 0.24'
_reflns_odcompleteness_completeness 99.43
_reflns_odcompleteness_iscentric 1
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_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C7(H7a,H7b)
2.b Aromatic/amide H refined with riding coordinates:
 C10(H10), C13(H13), C5(H5), C11(H11), C12(H12), N2(H2), C1(H1)
2.c Idealised Me refined as rotating group:
 C8(H8a,H8b,H8c), C15(H15a,H15b,H15c)
;
_olex2_submission_special_instructions 'No special instructions were received'