2-Nitroallyl carbonate-based green bifunctional reagents for catalytic asymmetric annulation reactions.
Kostenko, Alexey A.; Bykova, Kseniya A.; Kucherenko, Alexander S.; Komogortsev, Andrey N.; Lichitsky, Boris V.; Zlotin, Sergei G.; Organic & biomolecular chemistry 19 (2021) 1780–1786; doi:10.1039/d0ob02283g

data_7157863
_publ_section_title
;
 2-Nitroallyl carbonate-based green bifunctional reagents for catalytic
 asymmetric annulation reactions.
;
_journal_issue                   8
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              1780
_journal_page_last               1786
_journal_paper_doi               10.1039/d0ob02283g
_journal_volume                  19
_journal_year                    2021
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C19 H13 N O5'
_chemical_formula_sum            'C19 H13 N O5'
_chemical_formula_weight         335.30
_space_group_crystal_system      tetragonal
_space_group_IT_number           78
_space_group_name_Hall           'P 4cw'
_space_group_name_H-M_alt        'P 43'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_block_doi                 10.5517/ccdc.csd.cc26hp9q
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2020-10-27 deposited with the CCDC.	2021-02-01 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.42180(14)
_cell_length_b                   12.42180(14)
_cell_length_c                   9.8189(2)
_cell_measurement_reflns_used    9914
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      33.42
_cell_measurement_theta_min      2.32
_cell_volume                     1515.07(4)
_computing_cell_refinement       'SAINT (Bruker, 2018)'
_computing_data_collection       '<i>APEX3</i> (Bruker, 2018)'
_computing_data_reduction        'SAINT (Bruker, 2018)'
_computing_molecular_graphics
;
SHELXTL (Sheldrick, Acta Cryst., 2008, A64, 112-122)
;
_computing_publication_material
;
SHELXTL (Sheldrick, Acta Cryst., 2008, A64, 112-122)
;
_computing_structure_refinement
;
SHELXL-2018 (Sheldrick, Acta Cryst., 2015, C71, 3-8)
;
_computing_structure_solution
;
SHELXT, SHELXS-2013 (Sheldrick, Acta Cryst., 2015, A71, 3-8)
;
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 7.31
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker AXS D8 QUEST, Photon III detector'
_diffrn_measurement_method       '\f and \w shutterless scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0289
_diffrn_reflns_av_unetI/netI     0.0137
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            59697
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         33.419
_diffrn_reflns_theta_min         2.644
_diffrn_source                   'fine-focus sealed X-Ray tube'
_exptl_absorpt_coefficient_mu    0.108
_exptl_absorpt_correction_T_max  0.8499
_exptl_absorpt_correction_T_min  0.7971
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 SADABS 2016/2 (Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 2015, 48, 3-10).
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.470
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.173
_refine_diff_density_min         -0.111
_refine_diff_density_rms         0.026
_refine_ls_abs_structure_details
;
 Flack x determined using 2637 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.03(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     281
_refine_ls_number_reflns         5899
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0222
_refine_ls_R_factor_gt           0.0205
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0299P)^2^+0.0846P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0526
_refine_ls_wR_factor_ref         0.0541
_reflns_Friedel_coverage         0.905
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                5688
_reflns_number_total             5899
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ob02283g2.cif
_cod_data_source_block           KA152-3
_cod_depositor_comments          'Adding full bibliography for 7157863.cif.'
_cod_original_cell_volume        1515.07(5)
_cod_database_code               7157863
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.965
_shelx_estimated_absorpt_t_max   0.991
_shelx_res_checksum              16719