Tandem double acylation/[3,3]-rearrangement of aliphatic nitro compounds: a route to α-oxygenated oxime derivatives.
Antonova, Yulia A.; Nelyubina, Yulia V.; Sukhorukov, Alexey Yu; Ioffe, Sema L.; Tabolin, Andrey A.; Organic & biomolecular chemistry 17 (2019) 5997–6006; doi:10.1039/c9ob01005j

data_7156881
_publ_section_title
;
 Tandem double acylation/[3,3]-rearrangement of aliphatic nitro compounds:
 a route to \a-oxygenated oxime derivatives.
;
_journal_issue                   24
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              5997
_journal_page_last               6006
_journal_paper_doi               10.1039/c9ob01005j
_journal_volume                  17
_journal_year                    2019
_chemical_formula_moiety         'C24 H35 N O6'
_chemical_formula_sum            'C24 H35 N O6'
_chemical_formula_weight         433.55
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_primary     dual
_audit_creation_date             2019-03-28
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-03-28 deposited with the CCDC.    2019-05-29 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.6050(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   19.9226(4)
_cell_length_b                   12.6653(3)
_cell_length_c                   18.9998(4)
_cell_measurement_reflns_used    9375
_cell_measurement_temperature    120
_cell_measurement_theta_max      67.89
_cell_measurement_theta_min      4.16
_cell_volume                     4696.13(18)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      120
_diffrn_measured_fraction_theta_full 0.9982
_diffrn_measured_fraction_theta_max 0.9982
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0312
_diffrn_reflns_av_unetI/netI     0.0158
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            73945
_diffrn_reflns_theta_full        67.4847
_diffrn_reflns_theta_max         67.48
_diffrn_reflns_theta_min         2.26
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.712
_exptl_absorpt_correction_T_max  0.7530
_exptl_absorpt_correction_T_min  0.6806
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.1258 before and 0.0482 after correction.
The Ratio of minimum to maximum transmission is 0.9039.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.2263
_exptl_crystal_description       prism
_exptl_crystal_F_000             1878.2268
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.1833
_refine_diff_density_min         -0.2468
_refine_diff_density_rms         0.0442
_refine_ls_d_res_high            0.8345
_refine_ls_d_res_low             19.5153
_refine_ls_goodness_of_fit_ref   1.0336
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    104
_refine_ls_number_parameters     573
_refine_ls_number_reflns         8451
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0336
_refine_ls_R_factor_all          0.0381
_refine_ls_R_factor_gt           0.0330
_refine_ls_shift/su_max          0.0004
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0485P)^2^+1.1763P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0879
_refine_ls_wR_factor_ref         0.0923
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              23
_reflns_limit_h_min              -23
_reflns_limit_k_max              15
_reflns_limit_k_min              0
_reflns_limit_l_max              22
_reflns_limit_l_min              0
_reflns_number_gt                7371
_reflns_number_total             8451
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            c9ob01005j2.cif
_cod_data_source_block           a
_cod_depositor_comments          'Adding full bibliography for 7156881.cif.'
_cod_database_code               7156881
_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.a Ternary CH refined with riding coordinates:
 C13(H13), C13A(H13A)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7a,H7b), C14(H14a,H14b), C16(H16a,H16b), C17(H17a,H17b), C7A(H7Aa,H7Ab),
 C14A(H14c,H14d), C16A(H16c,H16d), C17A(H17c,H17d)
2.c Aromatic/amide H refined with riding coordinates:
 C20(H20), C21(H21), C22(H22), C23(H23), C24(H24), C20A(H20A), C21A(H21A),
 C22A(H22A), C23A(H23A), C24A(H24A)
2.d Idealised Me refined as rotating group:
 C4(H4a,H4b,H4c), C5(H5a,H5b,H5c), C6(H6a,H6b,H6c), C10(H10a,H10b,H10c),
 C11(H11a,H11b,H11c), C12(H12a,H12b,H12c), C18(H18a,H18b,H18c), C4A(H4Aa,H4Ab,
 H4Ac), C5A(H5Aa,H5Ab,H5Ac), C6A(H6Aa,H6Ab,H6Ac), C10A(H10d,H10e,H10f),
 C11A(H11d,H11e,H11f), C12A(H12d,H12e,H12f), C18A(H18d,H18e,H18f)
;
_olex2_submission_special_instructions 'No special instructions were received'