Vinylogous and stereoselective domino synthesis of pyrano[2,3-<i>c</i>]pyrroles from alkylidene meldrum's acids.
Savchuk, Mariia; Vo-Thanh, Giang; Oudeyer, Sylvain; Beucher, Hélène; Brière, Jean-François; Organic & biomolecular chemistry 22 (2024) 2948–2952; doi:10.1039/d4ob00233d

data_7159846
_publ_section_title
;
 Vinylogous and stereoselective domino synthesis of
 pyrano[2,3-<i>c</i>]pyrroles from alkylidene meldrum's acids.
;
_journal_issue                   15
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              2948
_journal_page_last               2952
_journal_paper_doi               10.1039/d4ob00233d
_journal_volume                  22
_journal_year                    2024
_chemical_formula_moiety         C33H25NO5
_chemical_formula_sum            'C33 H25 N O5'
_chemical_formula_weight         515.54
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   dual
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.5
_audit_creation_date             2023-10-23T12:21:45-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_update_record
;
2024-01-25 deposited with the CCDC.	2024-03-11 downloaded from the CCDC.
;
_cell_angle_alpha                70.3700(10)
_cell_angle_beta                 72.4580(10)
_cell_angle_gamma                67.8020(10)
_cell_formula_units_Z            2
_cell_length_a                   10.1201(2)
_cell_length_b                   11.3054(3)
_cell_length_c                   13.5515(3)
_cell_measurement_reflns_used    9890
_cell_measurement_temperature    300(2)
_cell_measurement_theta_max      25.64
_cell_measurement_theta_min      2.22
_cell_measurement_wavelength     0.71073
_cell_volume                     1324.77(5)
_computing_cell_refinement       'SAINT V8.40B integration software'
_computing_data_collection       'Bruker APEX2 software'
_computing_data_reduction        'SORTAV (Blessing, 1995)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_structure_solution    'SHELXD-2013/2 (Sheldrick, 2008)'
_diffrn_ambient_temperature      300(2)
_diffrn_detector                 'APEX-II CCD'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II'
_diffrn_measurement_method       '\f or \w oscillation scans'
_diffrn_orient_matrix_UB_11      0.106296
_diffrn_orient_matrix_UB_12      -0.033119
_diffrn_orient_matrix_UB_13      -0.030529
_diffrn_orient_matrix_UB_21      -0.022243
_diffrn_orient_matrix_UB_22      -0.041058
_diffrn_orient_matrix_UB_23      -0.045445
_diffrn_orient_matrix_UB_31      -0.008435
_diffrn_orient_matrix_UB_32      0.08343
_diffrn_orient_matrix_UB_33      -0.058281
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.056
_diffrn_reflns_av_unetI/netI     0.0396
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            9145
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_reduction_process
;
        Scaled and merged with Sortav
        R.H. Blessing, (1987) Cryst. Rev. 1, 3-58
        R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397
;
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.036
_diffrn_reflns_theta_min         2.476
_diffrn_source                   'sealed x-ray tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.292
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             540
_exptl_crystal_size_max          0.772
_exptl_crystal_size_mid          0.649
_exptl_crystal_size_min          0.245
_refine_diff_density_max         0.286
_refine_diff_density_min         -0.216
_refine_diff_density_rms         0.05
_refine_ls_extinction_coef       0.014(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     354
_refine_ls_number_reflns         9145
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0655
_refine_ls_R_factor_gt           0.052
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0620P)^2^+0.2299P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1389
_refine_ls_wR_factor_ref         0.1512
_reflns_Friedel_coverage         0
_reflns_number_gt                7346
_reflns_number_total             9145
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ob00233d2.cif
_cod_data_source_block           shelx
_cod_depositor_comments          'Adding full bibliography for 7159846.cif.'
_cod_database_code               7159846
_shelx_estimated_absorpt_t_min   0.936
_shelx_estimated_absorpt_t_max   0.979
_shelx_shelxl_version_number     2019/3
_shelx_res_checksum              58548