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_7231812
_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         'C39 H44 N2 O'
_chemical_formula_sum            'C39 H44 N2 O'
_chemical_formula_weight         556.76
_chemical_name_common            2c
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_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             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                69.67(5)
_cell_angle_beta                 86.47(3)
_cell_angle_gamma                73.49(3)
_cell_formula_units_Z            2
_cell_length_a                   10.525(2)
_cell_length_b                   12.498(7)
_cell_length_c                   13.969(6)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    297
_cell_measurement_theta_max      26.919
_cell_measurement_theta_min      20.035
_cell_volume                     1650.6(14)
_computing_cell_refinement       'CAD4 Express (Enraf Nonius, 1994)'
_computing_data_collection       'CAD4 Express (Enraf Nonius, 1994)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_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
;
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      297
_diffrn_detector                 'scintillation LiI'
_diffrn_detector_dtime           1.195
_diffrn_detector_type            'scintillation LiI'
_diffrn_measured_fraction_theta_full 0.968
_diffrn_measured_fraction_theta_max 0.964
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker-Enraf-Nonius MACH3'
_diffrn_measurement_method       'non-profiled \w/2\t scans'
_diffrn_orient_matrix_type
;
  x-axis points to radiation source
  the matrix is specified in reciprocal space
;
_diffrn_orient_matrix_UB_11      -0.072504
_diffrn_orient_matrix_UB_12      0.008285
_diffrn_orient_matrix_UB_13      0.048917
_diffrn_orient_matrix_UB_21      0.057823
_diffrn_orient_matrix_UB_22      0.020024
_diffrn_orient_matrix_UB_23      0.041509
_diffrn_orient_matrix_UB_31      -0.035180
_diffrn_orient_matrix_UB_32      0.086229
_diffrn_orient_matrix_UB_33      -0.041510
_diffrn_radiation_detector       'scintillation counter'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0287
_diffrn_reflns_av_unetI/netI     0.0336
_diffrn_reflns_Laue_measured_fraction_full 0.968
_diffrn_reflns_Laue_measured_fraction_max 0.964
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            6680
_diffrn_reflns_point_group_measured_fraction_full 0.968
_diffrn_reflns_point_group_measured_fraction_max 0.964
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.916
_diffrn_reflns_theta_min         3.377
_diffrn_source                   'Enraf Nonius FR590'
_diffrn_source_target            Cu
_diffrn_source_type              'fine-focus sealed tube'
_diffrn_standards_decay_%        1
_diffrn_standards_interval_time  120
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    0.507
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.120
_exptl_crystal_description       prism
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.27
_refine_diff_density_max         0.659
_refine_diff_density_min         -0.225
_refine_diff_density_rms         0.057
_refine_ls_extinction_coef       0.0084(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     388
_refine_ls_number_reflns         6348
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.1099
_refine_ls_R_factor_gt           0.0604
_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^)+(0.0998P)^2^+0.5316P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1600
_refine_ls_wR_factor_ref         0.1951
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4075
_reflns_number_total             6348
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8ra08220k2.cif
_cod_data_source_block           nany
_cod_original_cell_volume        1650.4(13)
_cod_database_code               7231812
_diffrn_standards_decay_corr_max 1.026
_diffrn_standards_decay_corr_min 0.956
_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 Ternary CH refined with riding coordinates:
 C34(H34), C25(H25), C22(H22), C37(H37)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C15(H15), C9(H9), C18(H18), C11(H11), C6(H6), C8(H8), C7(H7),
 C14(H14), C32(H32), C13(H13), C12(H12), C20(H20), C30(H30), C19(H19), C31(H31)
2.c Idealised Me refined as rotating group:
 C36(H36A,H36B,H36C), C23(H23A,H23B,H23C), C27(H27A,H27B,H27C), C35(H35A,H35B,
 H35C), C24(H24A,H24B,H24C), C39(H39A,H39B,H39C), C26(H26A,H26B,H26C), C38(H38A,
 H38B,H38C)
;
_shelx_res_checksum              4171
_shelx_hkl_checksum              61313
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'