Metal free oxidation of vinamidine derivatives: a simple synthesis of α-keto-β-diimine ligands
Tripathi, Monika; Regnier, Vianney; Ziani, Zakaria; Devillard, Marc; Philouze, Christian; Martin, David; RSC Advances 8 (2018) 38346–; doi:10.1039/C8RA08220K

data_7231815
_publ_section_title
;
 Metal free oxidation of vinamidine derivatives: a simple synthesis of
 \a-keto-\b-diimine ligands
;
_journal_issue                   67
_journal_name_full               'RSC Advances'
_journal_page_first              38346
_journal_paper_doi               10.1039/C8RA08220K
_journal_volume                  8
_journal_year                    2018
_chemical_formula_moiety         'C19 H22 N4 O'
_chemical_formula_sum            'C19 H22 N4 O'
_chemical_formula_weight         322.40
_chemical_name_common            2d
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2018-05-25
_audit_creation_method
;
Olex2 1.2
(compiled 2014.07.22 svn.r2960 for OlexSys, GUI svn.r4862)
;
_audit_update_record
;
2018-09-07 deposited with the CCDC.
2018-11-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.168(2)
_cell_length_b                   21.152(4)
_cell_length_c                   6.9588(14)
_cell_measurement_reflns_used    15859
_cell_measurement_temperature    200
_cell_measurement_theta_max      30.000
_cell_measurement_theta_min      1.926
_cell_volume                     1791.0(6)
_computing_cell_refinement       EvalCCD
_computing_data_collection       Collect
_computing_data_reduction        EvalCCD
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      200
_diffrn_detector                 'CCD area detector'
_diffrn_detector_type            KappaCCD
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device       '4 circles diffractometer'
_diffrn_measurement_device_type  'Bruker-AXS-enraf-nonius KappaCCD'
_diffrn_measurement_method       'Phi and omega scans'
_diffrn_radiation_collimation    'Montel optic'
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  'Multilayer mirrors'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0263
_diffrn_reflns_av_unetI/netI     0.0248
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            15859
_diffrn_reflns_point_group_measured_fraction_full 0.971
_diffrn_reflns_point_group_measured_fraction_max 0.943
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.000
_diffrn_reflns_theta_min         1.926
_diffrn_source                   'Incoatec ISG250'
_diffrn_source_target            Mo
_diffrn_source_type              'Microfocus sealed tube'
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.718632
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2004/1 (Bruker,2004) was used for absorption correction.
R(int) was 0.2649 before and 0.0302 after correction.
The Ratio of minimum to maximum transmission is 0.7186.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.196
_exptl_crystal_description       block
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.32
_refine_diff_density_max         0.173
_refine_diff_density_min         -0.234
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details
;
 Flack x determined using 1623 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.2(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     276
_refine_ls_number_reflns         4928
_refine_ls_number_restraints     193
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0560
_refine_ls_R_factor_gt           0.0451
_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^)+(0.0609P)^2^+0.2524P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1144
_refine_ls_wR_factor_ref         0.1241
_reflns_Friedel_coverage         0.762
_reflns_Friedel_fraction_full    0.939
_reflns_Friedel_fraction_max     0.883
_reflns_number_gt                4194
_reflns_number_total             4928
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8ra08220k2.cif
_cod_data_source_block           nany_CCDC3
_cod_original_cell_volume        1790.9(6)
_cod_database_code               7231815
_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. Restrained distances
 C14A-N4
 1.4 with sigma of 0.02
 N4-C14B
 1.4 with sigma of 0.02
 C14A-C15A
 1.4 with sigma of 0.02
 C15B-C14B
 1.4 with sigma of 0.02
 C14A-C19A
 1.4 with sigma of 0.02
 C14B-C19B
 1.4 with sigma of 0.02
3. Rigid bond restraints
 C14B, C15B, C19B, C18B, C17B, C16B, C15A, C16A, C17A, C18A, C19A, C14A
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
C14B \\sim C15B \\sim C19B \\sim C18B \\sim C17B \\sim C16B \\sim C15A \\sim
C16A \\sim C17A \\sim C18A \\sim C19A \\sim C14A: within 1.7A with sigma of
0.04 and sigma for terminal atoms of 0.08
5. Others
 Sof(C14B)=Sof(C15B)=Sof(H15B)=Sof(C19B)=Sof(H19B)=Sof(C18B)=Sof(H18B)=
 Sof(C17B)=Sof(H17B)=Sof(C16B)=Sof(H16B)=1-FVAR(1)
 Sof(C15A)=Sof(H15A)=Sof(C16A)=Sof(H16A)=Sof(C17A)=Sof(H17A)=Sof(C18A)=
 Sof(H18A)=Sof(C19A)=Sof(H19A)=Sof(C14A)=FVAR(1)
6.a Aromatic/amide H refined with riding coordinates:
 C13(H13), C9(H9), C11(H11), C12(H12), C15B(H15B), C10(H10), C19B(H19B),
 C18B(H18B), C17B(H17B), C16B(H16B), C15A(H15A), C16A(H16A), C17A(H17A),
 C18A(H18A), C19A(H19A)
6.b Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C), C4(H4A,H4B,H4C), C7(H7A,H7B,H7C), C6(H6A,H6B,H6C)
;
_shelx_res_checksum              13990
_shelx_hkl_checksum              62866
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'