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_7226555
_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         'C32 H22 Br N3 O4'
_chemical_formula_sum            'C32 H22 Br N3 O4'
_chemical_formula_weight         592.44
_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                 94.18(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.0358(18)
_cell_length_b                   11.317(2)
_cell_length_c                   22.376(7)
_cell_measurement_reflns_used    3554
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      23.5180
_cell_measurement_theta_min      3.5740
_cell_volume                     2787.2(11)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.867
_diffrn_measurement_device_type  'New Xcalibur, Ruby'
_diffrn_measurement_method       '\w 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  0.0318
_diffrn_reflns_av_sigmaI/netI    0.0547
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            14952
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         29.22
_diffrn_reflns_theta_min         2.69
_exptl_absorpt_coefficient_mu    1.517
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.76822
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.412
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1208
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.232
_refine_diff_density_min         -0.599
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     436
_refine_ls_number_reflns         6566
_refine_ls_number_restraints     10
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.1230
_refine_ls_R_factor_gt           0.0543
_refine_ls_shift/su_max          0.020
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0622P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1188
_refine_ls_wR_factor_ref         0.1408
_reflns_number_gt                3465
_reflns_number_total             6566
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            c6ra21981k2.cif
_cod_data_source_block           psu-119-vzh-89
_cod_original_cell_volume        2787.3(11)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7226555