Palladium-catalyzed asymmetric [4+2] annulation of vinyl benzoxazinanones with pyrazolone 4,5-diones to access spirobenzoxazine frameworks.
Chen, Ben-Hong; Liu, Shuai-Jiang; Zhao, Qian; Hou, Qiumeng; Yuan, Jia-Li; Zhan, Gu; Yang, Qian-Qian; Huang, Wei; Chemical communications (Cambridge, England) 59 (2023) 1233–1236; doi:10.1039/d2cc06621a

data_7131178
_publ_section_title
;
 Palladium-catalyzed asymmetric [4+2] annulation of vinyl benzoxazinanones
 with pyrazolone 4,5-diones to access spirobenzoxazine frameworks.
;
_journal_issue                   9
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              1233
_journal_page_last               1236
_journal_paper_doi               10.1039/d2cc06621a
_journal_volume                  59
_journal_year                    2023
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C27 H25 N3 O4 S'
_chemical_formula_sum            'C27 H25 N3 O4 S'
_chemical_formula_weight         487.56
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-06-01
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2022-07-11 deposited with the CCDC.	2022-12-30 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.0617(4)
_cell_length_b                   10.9968(5)
_cell_length_c                   27.6122(12)
_cell_measurement_reflns_used    1284
_cell_measurement_temperature    293.15
_cell_measurement_theta_max      30.27
_cell_measurement_theta_min      4.33
_cell_volume                     2447.9(2)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      293.15
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0515
_diffrn_reflns_av_unetI/netI     0.0375
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            21413
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.492
_diffrn_reflns_theta_min         3.201
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.495
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.323
_exptl_crystal_description       block
_exptl_crystal_F_000             1024
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.176
_refine_diff_density_min         -0.309
_refine_diff_density_rms         0.050
_refine_ls_abs_structure_details
;
 Flack x determined using 1485 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.006(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     339
_refine_ls_number_reflns         4512
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0468
_refine_ls_R_factor_gt           0.0401
_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^)+(0.0449P)^2^+0.3254P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0926
_refine_ls_wR_factor_ref         0.0983
_reflns_Friedel_coverage         0.739
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                3986
_reflns_number_total             4512
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cc06621a2.cif
_cod_data_source_block           20220516_0m_a
_cod_depositor_comments          'Adding full bibliography for 7131178.cif.'
_cod_database_code               7131178
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.853
_shelx_estimated_absorpt_t_min   0.725
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Sof(C2)=Sof(H2A)=Sof(H2B)=1-FVAR(1)
 Sof(C1)=Sof(H1A)=Sof(H1B)=FVAR(1)
 Sof(H00D)=Sof(C0AB)=Sof(H0AB)=1-FVAR(2)
 Sof(H00R)=Sof(C0AA)=Sof(H0AA)=FVAR(2)
3.a Ternary CH refined with riding coordinates:
 C00R(H00R), C00R(H00D)
3.b Aromatic/amide H refined with riding coordinates:
 C00E(H00E), C00I(H00I), C00J(H00J), C00K(H00K), C00L(H00L), C00O(H00O),
 C00P(H00P), C00Q(H00Q), C00T(H00T), C00U(H00U), C00V(H00V), C00W(H00W),
 C0AA(H0AA), C0AB(H0AB)
3.c X=CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B)
3.d Idealised Me refined as rotating group:
 C00N(H00A,H00B,H00C), C00S(H00F,H00G,H00H), C00X(H00M,H00N,H00S)
;
_olex2_submission_special_instructions 'No special instructions were received'