Efficient and phosphine-free bidentate N-heterocyclic carbene/ruthenium catalytic systems for the dehydrogenative amidation of alcohols and amines
Wu, Xuan-Jun; Wang, Hua-Jing; Yang, Zhao-Qi; Tang, Xiao-Sheng; Yuan, Ye; Su, Wei; Chen, Cheng; Verpoort, Francis; Organic Chemistry Frontiers 6 (2019) 563–; doi:10.1039/C8QO00902C

data_1554450
_publ_section_title
;
 Efficient and phosphine-free bidentate N-heterocyclic carbene/ruthenium
 catalytic systems for the dehydrogenative amidation of alcohols and
 amines
;
_journal_issue                   5
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              563
_journal_paper_doi               10.1039/C8QO00902C
_journal_volume                  6
_journal_year                    2019
_chemical_formula_moiety         'C27 H31 I N2 Ru'
_chemical_formula_sum            'C27 H31 I N2 Ru'
_chemical_formula_weight         611.51
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     heavy
_audit_creation_date             2018-07-06
_audit_creation_method
;
Olex2 1.2
(compiled 2018.04.26 svn.r3504 for OlexSys, GUI svn.r5492)
;
_audit_update_record
;
2018-07-07 deposited with the CCDC.
2018-11-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.269(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.329(2)
_cell_length_b                   7.7727(10)
_cell_length_c                   21.254(3)
_cell_measurement_reflns_used    6321
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.73
_cell_measurement_theta_min      2.67
_cell_volume                     2521.7(6)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0349
_diffrn_reflns_av_unetI/netI     0.0328
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            16912
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        24.997
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_min         1.924
_exptl_absorpt_coefficient_mu    1.862
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'dark orange'
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.611
_exptl_crystal_description       block
_exptl_crystal_F_000             1216
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.628
_refine_diff_density_min         -0.480
_refine_diff_density_rms         0.080
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     286
_refine_ls_number_reflns         4435
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0375
_refine_ls_R_factor_gt           0.0299
_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^)+(0.0372P)^2^+1.6998P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0729
_refine_ls_wR_factor_ref         0.0763
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3801
_reflns_number_total             4435
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8qo00902c2.cif
_cod_data_source_block           mo_180706b_0m
_cod_database_code               1554450
_shelx_shelxl_version_number     2014/7
_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:
 C18(H18)
2.b Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C23(H23), C8(H8), C11(H11), C24(H24), C26(H26), C25(H25), C27(H27),
 C16(H16), C7(H7)
2.d Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C21(H21A,H21B,H21C), C13(H13A,H13B,H13C), C14(H14A,H14B,
 H14C), C6(H6A,H6B,H6C), C19(H19A,H19B,H19C)
;
_olex2_submission_special_instructions 'No special instructions were received'