New method for in-situ generation of enolate-iminium 1,4-dipoles for [4+2] and [4+1] dipolar heterocycloaddition reactions
Zhulanov, Vladimir E.; Dmitriev, Maksim V.; Maslivets, Andrey N.; Rubin, Michael; RSC Adv.  (2016) –; doi:10.1039/C6RA21981K

data_7226553
_publ_section_title
;
 New method for in-situ generation of enolate-iminium 1,4-dipoles for
 [4+2] and [4+1] dipolar heterocycloaddition reactions
;
_journal_name_full               'RSC Adv.'
_journal_paper_doi               10.1039/C6RA21981K
_journal_year                    2016
_chemical_formula_moiety         'C50 H36 N4 O8'
_chemical_formula_sum            'C50 H36 N4 O8'
_chemical_formula_weight         820.83
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_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
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2016-03-02 deposited with the CCDC.
2016-09-12 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 93.606(13)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.0225(15)
_cell_length_b                   19.081(6)
_cell_length_c                   21.963(3)
_cell_measurement_reflns_used    5691
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.3150
_cell_measurement_theta_min      3.4230
_cell_volume                     4191.9(16)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.857
_diffrn_measurement_device_type  'Xcalibur, Ruby'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0475
_diffrn_reflns_av_sigmaI/netI    0.0675
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            31691
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         29.70
_diffrn_reflns_theta_min         2.83
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.63401
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.301
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1712
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.193
_refine_diff_density_min         -0.272
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.990
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     561
_refine_ls_number_reflns         10203
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.990
_refine_ls_R_factor_all          0.1301
_refine_ls_R_factor_gt           0.0608
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0731P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1307
_refine_ls_wR_factor_ref         0.1614
_reflns_number_gt                5452
_reflns_number_total             10203
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            c6ra21981k2.cif
_cod_data_source_block           psu-24-md-306
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7226553