Azomethine ylide cycloaddition of 1,3-dienyl esters: highly regio- and diastereoselective synthesis of functionalized pyrrolidinochromenes.
Bakthadoss, Manickam; Mushaf, Mohammad; Agarwal, Vishal; Reddy, Tadiparthi Thirupathi; Sharada, Duddu S.; Organic & biomolecular chemistry 20 (2022) 778–782; doi:10.1039/d1ob02042k

data_7158454
_publ_section_title
;
 Azomethine ylide cycloaddition of 1,3-dienyl esters: highly regio- and
 diastereoselective synthesis of functionalized pyrrolidinochromenes.
;
_journal_issue                   4
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              778
_journal_page_last               782
_journal_paper_doi               10.1039/d1ob02042k
_journal_volume                  20
_journal_year                    2022
_chemical_formula_moiety         'C23 H23 N O5'
_chemical_formula_sum            'C7 H0 N16 O6'
_chemical_formula_weight         404.23
_chemical_name_common            Tetrahydrochromeno[4,3-b]pyrrole
_chemical_name_systematic
'dimethyl (E)-3-styryl-1,2,3,9b-tetrahydrochromeno[4,3-b]pyrrole-2,3a(4H)-dicarboxylate'
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2019-07-13
_audit_creation_method
;
  Olex2 1.2-ac2
  (compiled 2012.03.27 svn.r2268, GUI svn.r4156)
;
_audit_update_record
;
2019-07-21 deposited with the CCDC.	2021-12-20 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 95.637(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.2643(9)
_cell_length_b                   7.5844(6)
_cell_length_c                   21.7321(16)
_cell_measurement_reflns_used    3172
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.0856
_cell_measurement_theta_min      3.1560
_cell_volume                     2011.7(3)
_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
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    'J. Appl. Cryst. (2007) 40, 786-790'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 15.9821
_diffrn_measured_fraction_theta_full 0.9964
_diffrn_measured_fraction_theta_max 0.9752
_diffrn_measurement_details
;
  1 omega  -86.00   -1.00   1.0000   40.0500
omega____ theta____ kappa____ phi______ frames
    -      -16.8710  -57.0000  -90.0000 85

  2 omega  -83.00    2.00   1.0000   40.0500
omega____ theta____ kappa____ phi______ frames
    -      -16.8710  -57.0000    0.0000 85

  3 omega  -11.00   19.00   1.0000   40.0500
omega____ theta____ kappa____ phi______ frames
    -      -16.8710  -99.0000 -150.0000 30

  4 omega   35.00   63.00   1.0000   40.0500
omega____ theta____ kappa____ phi______ frames
    -       19.5272  178.0000 -150.0000 28

  5 omega  -38.00   22.00   1.0000   40.0500
omega____ theta____ kappa____ phi______ frames
    -      -16.8710   57.0000   30.0000 60
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0242130000
_diffrn_orient_matrix_UB_12      0.0135805000
_diffrn_orient_matrix_UB_13      -0.0279382000
_diffrn_orient_matrix_UB_21      0.0519457000
_diffrn_orient_matrix_UB_22      0.0104409000
_diffrn_orient_matrix_UB_23      0.0170386000
_diffrn_orient_matrix_UB_31      0.0094158000
_diffrn_orient_matrix_UB_32      -0.0919947000
_diffrn_orient_matrix_UB_33      -0.0022145000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0348
_diffrn_reflns_av_unetI/netI     0.0506
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            11384
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         29.15
_diffrn_reflns_theta_min         3.16
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.117
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.92914
_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            Colorless
_exptl_crystal_density_diffrn    1.335
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             808
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: DCM and DMF'
_refine_diff_density_max         0.213
_refine_diff_density_min         -0.164
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       0.0085(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     268
_refine_ls_number_reflns         4689
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.1011
_refine_ls_R_factor_gt           0.0606
_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^)+(0.0677P)^2^+0.6927P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1565
_refine_ls_wR_factor_ref         0.1819
_reflns_number_gt                2904
_reflns_number_total             4689
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d1ob02042k2.cif
_cod_data_source_block           mb-va-vb-f-1-ds-s
_cod_depositor_comments          'Adding full bibliography for 7158454.cif.'
_cod_database_code               7158454
_chemical_oxdiff_formula         'C23 H20 O5 N1'
_chemical_oxdiff_usercomment     'COLOURLESS BLOCK, 298K, 0.42 0.34 0.26'
_reflns_odcompleteness_completeness 99.64
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32