Solvent- and Base-Free Synthesis of Wax Esters from Fatty Acid Methyl Esters by Consecutive One-Pot, Two-Step Catalysis.
Nguyen, Duc Hanh; Raffa, Guillaume; Morin, Yohann; Desset, Simon Laurent; Capet, Frédéric; nardello-rataj, veronique; Dumeignil, Franck Yves; Gauvin, Régis; Green Chem.  (2017) –; doi:10.1039/C7GC02764H

data_7229371
_publ_section_title
;
 Solvent- and Base-Free Synthesis of Wax Esters from Fatty Acid Methyl
 Esters by Consecutive One-Pot, Two-Step Catalysis.
;
_journal_name_full               'Green Chem.'
_journal_paper_doi               10.1039/C7GC02764H
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C17 H40 B N O P2 Ru'
_chemical_formula_sum            'C17 H40 B N O P2 Ru'
_chemical_formula_weight         448.32
_chemical_name_systematic
'Carbonyl(trihydroborato)(hydruro)[bis(2-diisopropylphosphinoethyl)amido] ruthenium(II)'
_chemical_properties_physical
', Air-sensitive,Moisture-sensitive,Oxygen-sensitive'
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2017-01-18
_audit_creation_method
;
Olex2 1.2
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_audit_update_record
;
2017-06-21 deposited with the CCDC.
2017-10-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   14.1736(5)
_cell_length_b                   15.6168(7)
_cell_length_c                   20.0291(8)
_cell_measurement_reflns_used    9859
_cell_measurement_temperature    99.98
_cell_measurement_theta_max      30.16
_cell_measurement_theta_min      2.61
_cell_volume                     4433.4(3)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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    'XT (Sheldrick, 2015a)'
_diffrn_ambient_temperature      99.98
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0619
_diffrn_reflns_av_unetI/netI     0.0494
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            80842
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         30.509
_diffrn_reflns_theta_min         1.653
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.855
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6981
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0697 before and 0.0580 after correction.
The Ratio of minimum to maximum transmission is 0.9357.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.343
_exptl_crystal_description       prism
_exptl_crystal_F_000             1888
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: toluene and n-pentane'
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.413
_refine_diff_density_min         -0.417
_refine_diff_density_rms         0.081
_refine_ls_abs_structure_details
;
 Flack x determined using 4793 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.022(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     463
_refine_ls_number_reflns         13439
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.017
_refine_ls_R_factor_all          0.0416
_refine_ls_R_factor_gt           0.0302
_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^)+(0.0160P)^2^+0.8064P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0493
_refine_ls_wR_factor_ref         0.0528
_reflns_Friedel_coverage         0.825
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.990
_reflns_number_gt                11682
_reflns_number_total             13439
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7gc02764h2.cif
_cod_data_source_block           mo_dhng285
_cod_database_code               7229371
_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:
 C14(H14), C31(H31), C11(H11), C4(H4), C28(H28), C21(H21), C1(H1), C18(H18)
2.b Secondary CH2 refined with riding coordinates:
 C27(H27A,H27B), C8(H8A,H8B), C7(H7A,H7B), C24(H24A,H24B), C25(H25A,H25B),
 C26(H26A,H26B), C9(H9A,H9B), C10(H10A,H10B)
2.c Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C6(H6A,H6B,H6C), C5(H5A,H5B,H5C), C12(H12A,H12B,H12C),
 C23(H23A,H23B,H23C), C32(H32A,H32B,H32C), C30(H30A,H30B,H30C), C3(H3A,H3B,H3C),
  C22(H22A,H22B,H22C), C29(H29A,H29B,H29C), C19(H19A,H19B,H19C), C2(H2D,H2E,
 H2F), C33(H33A,H33B,H33C), C15(H15A,H15B,H15C), C20(H20A,H20B,H20C), C13(H13A,
 H13B,H13C)
;
_shelx_res_checksum              10053
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'