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_7231814
_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 H23 N2 O, B F4, 2.2(C0.23 H0.45 Cl0.45)'
_chemical_formula_sum            'C19.5 H24 B Cl F4 N2 O'
_chemical_formula_weight         424.67
_chemical_name_common            7H+
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_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                 91.17(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.1627(18)
_cell_length_b                   8.6433(17)
_cell_length_c                   26.423(5)
_cell_measurement_reflns_used    20252
_cell_measurement_temperature    200
_cell_measurement_theta_max      25.000
_cell_measurement_theta_min      1.542
_cell_volume                     2092.2(7)
_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 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device       '4 circles diffractometer'
_diffrn_measurement_device_type  Incoatec-Bruker-AXS-enraf-noniusKappaCCD
_diffrn_measurement_method       'Phi and omega scans'
_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  0.0734
_diffrn_reflns_av_unetI/netI     0.0412
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            20252
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        24.996
_diffrn_reflns_theta_max         24.996
_diffrn_reflns_theta_min         1.542
_diffrn_source                   'Incoatec ISG250'
_diffrn_source_target            Mo
_diffrn_source_type              'Microfocus sealed tube'
_exptl_absorpt_coefficient_mu    0.230
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.313663
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2004/1 (Bruker,2004) was used for absorption correction. R(int) was 0.1483 before and 0.0991 after correction. The Ratio of minimum to maximum transmission is 0.3137. The \l/2 correction factor is 0.0015.'
_exptl_crystal_colour            brown
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.348
_exptl_crystal_description       block
_exptl_crystal_F_000             884
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.414
_refine_diff_density_min         -0.297
_refine_diff_density_rms         0.074
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.106
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     319
_refine_ls_number_reflns         3651
_refine_ls_number_restraints     139
_refine_ls_restrained_S_all      1.177
_refine_ls_R_factor_all          0.0856
_refine_ls_R_factor_gt           0.0670
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0715P)^2^+1.9494P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1712
_refine_ls_wR_factor_ref         0.1887
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2838
_reflns_number_total             3651
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8ra08220k2.cif
_cod_data_source_block           nany_CCDC2
_cod_original_formula_sum        'C19.50 H24 B Cl F4 N2 O'
_cod_database_code               7231814
_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, All O(H) groups
2. Restrained distances
 C20B-Cl1B
 1.7 with sigma of 0.02
 C20B-Cl1B_$1
 1.7 with sigma of 0.02
 C20A-Cl1A
 1.7 with sigma of 0.02
 C20A-Cl1A_$1
 1.7 with sigma of 0.02
 O1B-C2
 1.4 with sigma of 0.02
3. Rigid bond restraints
 C20B, Cl1B, C20A, Cl1A
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 F2A, F2B, F3A, F3B, F4, F1A, F1B
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C2, O1B, O1A
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
C20B \\sim Cl1B \\sim C20A \\sim Cl1A: within 1.7A with sigma of 0.04 and sigma
for terminal atoms of 0.08
F2A \\sim F2B \\sim F3A \\sim F3B \\sim F1A \\sim F1B \\sim F4 \\sim B1: within
1.7A with sigma of 0.04 and sigma for terminal atoms of 0.08
O1B \\sim O1A \\sim C2: within 1.7A with sigma of 0.04 and sigma for terminal
atoms of 0.08
Uanis(O1B) = Uanis(O1A)
5. Others
 Sof(Cl1B)=1-FVAR(1)
 Sof(C20B)=Sof(H20B)=Sof(H20A)=0.5*(1-FVAR(2))
 Sof(C20A)=Sof(H20D)=Sof(H20C)=0.5*FVAR(2)
 Sof(Cl1A)=FVAR(1)
 Sof(F2B)=Sof(F3B)=Sof(F1B)=1-FVAR(2)
 Sof(F2A)=Sof(F3A)=Sof(F1A)=FVAR(2)
 Sof(O1B)=Sof(H1B)=1-FVAR(3)
 Sof(O1A)=Sof(H1A)=FVAR(3)
6.a Secondary CH2 refined with riding coordinates:
 C20B(H20B,H20A), C20A(H20D,H20C)
6.b Aromatic/amide H refined with riding coordinates:
 C9(H9), C19(H19), C15(H15), C13(H13), C12(H12), C18(H18), C16(H16), C11(H11),
 C10(H10), C17(H17)
6.c Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C6(H6A,H6B,H6C), C5(H5A,H5B,H5C), C4(H4A,H4B,H4C)
6.d Idealised tetrahedral OH refined as rotating group:
 O1B(H1B), O1A(H1A)
;
_shelx_res_checksum              17961
_shelx_hkl_checksum              12124
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'