A bifunctional squaramide-catalysed enantioselective vinylogous Michael addition/cyclization cascade reaction of 4-unsaturated isoxazol-5-ones and α,α-dicyanoalkenes.
Wang, Yu; Niu, Cheng; Xie, Dong-Hua; Du, Da-Ming; Organic & biomolecular chemistry 19 (2021) 8572–8577; doi:10.1039/d1ob01256h

data_7158299
_publ_section_title
;
 A bifunctional squaramide-catalysed enantioselective vinylogous Michael
 addition/cyclization cascade reaction of 4-unsaturated isoxazol-5-ones
 and \a,\a-dicyanoalkenes.
;
_journal_issue                   39
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              8572
_journal_page_last               8577
_journal_paper_doi               10.1039/d1ob01256h
_journal_volume                  19
_journal_year                    2021
_chemical_absolute_configuration ad
_chemical_formula_sum            'C22 H16 Br N3 O2'
_chemical_formula_weight         434.29
_chemical_melting_point          452.0(10)
_chemical_name_systematic
'(5S,10R)-8-(4-Bromophenyl)-6-imino-4-methyl-1-oxo-10-phenyl-2-oxa-3-azaspiro[4.5]deca-3,7-diene-7-carbonitrile'
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2021-06-27 deposited with the CCDC.	2021-09-13 downloaded from the CCDC.
;
_cell_angle_alpha                75.605(8)
_cell_angle_beta                 86.331(8)
_cell_angle_gamma                89.054(9)
_cell_formula_units_Z            2
_cell_length_a                   6.062(2)
_cell_length_b                   12.279(5)
_cell_length_c                   13.666(5)
_cell_measurement_reflns_used    5332
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      20.34
_cell_measurement_theta_min      2.57
_cell_volume                     983.3(6)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  CCD
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0788
_diffrn_reflns_av_unetI/netI     0.1337
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            20517
_diffrn_reflns_point_group_measured_fraction_full 0.942
_diffrn_reflns_point_group_measured_fraction_max 0.937
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.279
_diffrn_reflns_theta_min         3.084
_exptl_absorpt_coefficient_mu    2.113
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.467
_exptl_crystal_description       block
_exptl_crystal_F_000             440
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Petroleum ether/ethyl acetate 5:1'
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_transmission_factor_max   0.864
_exptl_transmission_factor_min   0.864
_refine_diff_density_max         0.263
_refine_diff_density_min         -0.378
_refine_diff_density_rms         0.057
_refine_ls_abs_structure_details
;
 Flack x determined using 1299 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.023(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.901
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     507
_refine_ls_number_reflns         6734
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      0.901
_refine_ls_R_factor_all          0.1278
_refine_ls_R_factor_gt           0.0433
_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^)+(0.0232P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0777
_refine_ls_wR_factor_ref         0.0977
_reflns_Friedel_coverage         0.897
_reflns_Friedel_fraction_full    0.891
_reflns_Friedel_fraction_max     0.886
_reflns_number_gt                3537
_reflns_number_total             6734
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ob01256h2.cif
_cod_data_source_block           1_b
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_melting_point' value '451-453' was changed to
'452.0(10)' -- the average value was taken and precision was
estimated.

data item '_chemical_absolute_configuration' value 'AD' was changed
to 'ad' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 

 Adding full bibliography for 7158299.cif.
;
_cod_database_code               7158299
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.677
_shelx_estimated_absorpt_t_max   0.677
_shelx_res_checksum              51949