Synthesis of oxalamides by acceptorless dehydrogenative coupling of ethylene glycol and amines and the reverse hydrogenation catalyzed by ruthenium
Zou, You-Quan; Zhou, Quan-Quan; Diskin-Posner, Yael; Ben-David, Yehoshoa; Milstein, David; Chemical Science  (2020) –; doi:10.1039/D0SC02065F

data_1558388
_publ_section_title
;
 Synthesis of oxalamides by acceptorless dehydrogenative coupling of
 ethylene glycol and amines and the reverse hydrogenation catalyzed by
 ruthenium
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D0SC02065F
_journal_year                    2020
_chemical_formula_moiety         'C25 H39 N2 O3 P Ru'
_chemical_formula_sum            'C25 H39 N2 O3 P Ru'
_chemical_formula_weight         547.62
_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'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2019-10-07 deposited with the CCDC.	2020-06-22 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.084(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.5765(2)
_cell_length_b                   12.9092(3)
_cell_length_c                   21.0501(5)
_cell_measurement_reflns_used    53513
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      34.9710
_cell_measurement_theta_min      1.8200
_cell_volume                     2562.12(10)
_computing_cell_refinement       'CrysAlisPro 1.171.40.57a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.57a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.57a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.925
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, Pilatus 300K'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0549
_diffrn_reflns_av_unetI/netI     0.0302
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.925
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            97956
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.925
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         35.017
_diffrn_reflns_theta_min         1.859
_exptl_absorpt_coefficient_mu    0.702
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.746
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.57a (Rigaku Oxford Diffraction, 2019)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_diffrn    1.420
_exptl_crystal_description       prism
_exptl_crystal_F_000             1144
_exptl_crystal_size_max          0.374
_exptl_crystal_size_mid          0.070
_exptl_crystal_size_min          0.061
_refine_diff_density_max         1.526
_refine_diff_density_min         -1.090
_refine_diff_density_rms         0.103
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.103
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     300
_refine_ls_number_reflns         10440
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.103
_refine_ls_R_factor_all          0.0435
_refine_ls_R_factor_gt           0.0368
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0222P)^2^+4.6792P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0840
_refine_ls_wR_factor_ref         0.0858
_reflns_Friedel_coverage         0.000
_reflns_number_gt                9135
_reflns_number_total             10440
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0sc02065f2.cif
_cod_data_source_block           m2195
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1558388
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.779
_shelx_estimated_absorpt_t_max   0.958
_shelx_res_checksum              72544