Construction of α-methoxyimidoyl ketonitrones via phosphite-mediated addition of α-keto N-tert-butanesulfinyl imidates to nitrosoarenes.
Feng, Jie; Ma, Peng-Ju; Zeng, Yong-Ming; Xu, Yan-Jun; Lu, Chong-Dao; Chemical communications (Cambridge, England) 54 (2018) 2882–2885; doi:10.1039/c8cc00345a

data_7121329
_publ_section_title
;
 Construction of \a-methoxyimidoyl ketonitrones via phosphite-mediated
 addition of \a-keto N-tert-butanesulfinyl imidates to nitrosoarenes.
;
_journal_issue                   23
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              2882
_journal_page_last               2885
_journal_paper_doi               10.1039/c8cc00345a
_journal_volume                  54
_journal_year                    2018
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C19 H21 F N2 O3 S'
_chemical_formula_sum            'C19 H21 F N2 O3 S'
_chemical_formula_weight         376.44
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_symmetry_space_group_name_Hall  'P 1'
_symmetry_space_group_name_H-M   'P 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2017-11-22
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2018-01-08 deposited with the CCDC.
2018-02-26 downloaded from the CCDC.
;
_cell_angle_alpha                76.975(2)
_cell_angle_beta                 89.282(2)
_cell_angle_gamma                79.014(2)
_cell_formula_units_Z            4
_cell_length_a                   11.4001(18)
_cell_length_b                   12.5665(19)
_cell_length_c                   14.190(2)
_cell_measurement_reflns_used    2060
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      20.116
_cell_measurement_theta_min      2.306
_cell_volume                     1943.3(5)
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.959
_diffrn_measurement_device_type  bruker-CCD
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0253
_diffrn_reflns_av_unetI/netI     0.0805
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.959
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            11861
_diffrn_reflns_point_group_measured_fraction_full 0.604
_diffrn_reflns_point_group_measured_fraction_max 0.575
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.423
_diffrn_reflns_theta_min         2.306
_exptl_absorpt_coefficient_mu    0.196
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9174
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0540 before and 0.0392 after correction.
The Ratio of minimum to maximum transmission is 0.9174.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.287
_exptl_crystal_description       block
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.352
_exptl_crystal_size_mid          0.193
_exptl_crystal_size_min          0.183
_refine_diff_density_max         0.248
_refine_diff_density_min         -0.227
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details
;
 Flack x determined using 961 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.15(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.998
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     953
_refine_ls_number_reflns         10200
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      0.998
_refine_ls_R_factor_all          0.1061
_refine_ls_R_factor_gt           0.0526
_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^)+(0.0545P)^2^]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1105
_refine_ls_wR_factor_ref         0.1366
_reflns_Friedel_coverage         0.199
_reflns_Friedel_fraction_full    0.225
_reflns_Friedel_fraction_max     0.191
_reflns_number_gt                5911
_reflns_number_total             10200
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8cc00345a2.cif
_cod_data_source_block           4k'
_cod_depositor_comments
'Adding full bibliography for 7121328--7121333.cif.'
_cod_database_code               7121329
_shelxl_version_number           2013-2
_shelx_estimated_absorpt_t_max   0.965
_shelx_estimated_absorpt_t_min   0.934
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C38(H38), C64(H64), C61(H61), C62(H62), C76(H76), C72(H72), C27(H27),
 C34(H34), C24(H24), C36(H36), C26(H26), C74(H74), C65(H65), C23(H23), C73(H73),
  C35(H35), C75(H75), C37(H37), C4(H4), C8(H8), C7(H7), C17(H17), C19(H19),
 C5(H5), C15(H15), C18(H18), C16(H16), C53(H53), C46(H46), C55(H55), C45(H45),
 C42(H42), C54(H54), C57(H57), C56(H56), C43(H43)
2.b Idealised Me refined as rotating group:
 C30(H30A,H30B,H30C), C66(H66A,H66B,H66C), C32(H32A,H32B,H32C), C69(H69A,H69B,
 H69C), C68(H68A,H68B,H68C), C28(H28A,H28B,H28C), C70(H70A,H70B,H70C), C31(H31A,
 H31B,H31C), C12(H12A,H12B,H12C), C9(H9A,H9B,H9C), C13(H13A,H13B,H13C),
 C11(H11A,H11B,H11C), C50(H50A,H50B,H50C), C47(H47A,H47B,H47C), C49(H49A,H49B,
 H49C), C51(H51A,H51B,H51C)
;