Asymmetric synthesis of chiral 1,2-oxazinane and hexahydropyridazin spirocyclic scaffolds by organocatalytic [4 + 2] cycloaddition
Tian, Heng-Zhi; Tang, Qing-Gang; Lin, Guo-Qiang; Sun, Xing-Wen; RSC Advances 12 (2022) 15713–15717; doi:10.1039/D2RA02759C

data_7244983
_publ_section_title
;
 Asymmetric synthesis of chiral 1,2-oxazinane and hexahydropyridazin
 spirocyclic scaffolds by organocatalytic [4 + 2] cycloaddition
;
_journal_issue                   25
_journal_name_full               'RSC Advances'
_journal_page_first              15713
_journal_page_last               15717
_journal_paper_doi               10.1039/D2RA02759C
_journal_volume                  12
_journal_year                    2022
_chemical_absolute_configuration ad
_chemical_formula_sum            'C20 H26 N2 O6'
_chemical_formula_weight         390.43
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2022-02-21 deposited with the CCDC.	2022-05-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.54
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   11.2293(6)
_cell_length_b                   8.1032(5)
_cell_length_c                   11.2293(6)
_cell_measurement_reflns_used    9144
_cell_measurement_temperature    274(2)
_cell_measurement_theta_max      72.63
_cell_measurement_theta_min      4.00
_cell_volume                     1004.55(10)
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      274(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0591
_diffrn_reflns_av_unetI/netI     0.0611
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            9600
_diffrn_reflns_point_group_measured_fraction_full 0.784
_diffrn_reflns_point_group_measured_fraction_max 0.765
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.847
_diffrn_reflns_theta_min         4.004
_exptl_absorpt_coefficient_mu    0.793
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.291
_exptl_crystal_description       plate
_exptl_crystal_F_000             416
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.070
_refine_diff_density_max         0.334
_refine_diff_density_min         -0.256
_refine_diff_density_rms         0.058
_refine_ls_abs_structure_details
;
 Flack x determined using 879 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.02(14)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     265
_refine_ls_number_reflns         3056
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.091
_refine_ls_R_factor_all          0.0439
_refine_ls_R_factor_gt           0.0434
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0651P)^2^+0.0605P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1008
_refine_ls_wR_factor_ref         0.1016
_reflns_Friedel_coverage         0.448
_reflns_Friedel_fraction_full    0.541
_reflns_Friedel_fraction_max     0.511
_reflns_number_gt                2984
_reflns_number_total             3056
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ra02759c2.cif
_cod_data_source_block           20190417tangQG_0ma
_cod_original_cell_volume        1004.56(10)
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7244983
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.797
_shelx_estimated_absorpt_t_max   0.947
_shelx_res_checksum              49275