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_7059467
_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         'C14 H15 N O3'
_chemical_formula_sum            'C14 H15 N O3'
_chemical_formula_weight         245.27
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-I 2ya'
_space_group_name_H-M_alt        'I 1 2/a 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2019-03-27
_audit_creation_method
;
Olex2 1.2-ac3
(compiled 2016.03.30 svn.r3266 for Rigaku Oxford Diffraction, GUI svn.r5168)
;
_audit_update_record
;
2019-03-26 deposited with the CCDC.	2020-03-17 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 103.173(13)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   25.920(3)
_cell_length_b                   5.4308(6)
_cell_length_c                   18.988(2)
_cell_measurement_reflns_used    1406
_cell_measurement_temperature    295
_cell_measurement_theta_max      29.1191
_cell_measurement_theta_min      3.8301
_cell_volume                     2602.5(5)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_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      295
_diffrn_detector_area_resol_mean 15.9821
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.853
_diffrn_measurement_details
;
  1 omega  -37.00   48.00   1.0000   65.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.3397   57.0000 -150.0000 85

  2 omega   -1.00   25.00   1.0000   65.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.3397  -99.0000   90.0000 26

  3 omega  -61.00   56.00   1.0000   65.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.3397   19.0000  -30.0000 117

  4 omega  -54.00  -20.00   1.0000   65.0000
omega____ theta____ kappa____ phi______ frames
    -       19.0585  -21.0000   10.0000 34
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0006552000
_diffrn_orient_matrix_UB_12      -0.0079075000
_diffrn_orient_matrix_UB_13      -0.0370103000
_diffrn_orient_matrix_UB_21      -0.0264265000
_diffrn_orient_matrix_UB_22      -0.0450249000
_diffrn_orient_matrix_UB_23      -0.0081901000
_diffrn_orient_matrix_UB_31      -0.0096816000
_diffrn_orient_matrix_UB_32      0.1224220000
_diffrn_orient_matrix_UB_33      -0.0053443000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0383
_diffrn_reflns_av_unetI/netI     0.0461
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            6451
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         29.18
_diffrn_reflns_theta_min         3.84
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85643
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.252
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1040
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.193
_refine_diff_density_min         -0.200
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         3012
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.1071
_refine_ls_R_factor_gt           0.0615
_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^)+(0.0819P)^2^+0.9382P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1544
_refine_ls_wR_factor_ref         0.1904
_reflns_number_gt                1786
_reflns_number_total             3012
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d0nj00231c3.cif
_cod_data_source_block           hsp-ahp-i-272-s
_cod_depositor_comments
;Adding full bibliography for 7059467--7059468.cif.

 Adding full bibliography for 7059467--7059468.cif.
;
_cod_original_cell_volume        2602.5(6)
_cod_database_code               7059467
_chemical_oxdiff_formula         'C19 H15 O3 N'
_chemical_oxdiff_usercomment     ' COLOURLESS PLATE, 295K, 0.42 0.40 0.05'
_reflns_odcompleteness_completeness 98.62
_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, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C5(H5)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C17(H17A,H17B)
2.c Aromatic/amide H refined with riding coordinates:
 N2(H2), C7(H7), C12(H12), C13(H13), C14(H14), C15(H15), C16(H16)
2.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_olex2_submission_special_instructions 'No special instructions were received'