Highly active bidentate N-heterocyclic carbene/ruthenium complexes performing dehydrogenative coupling of alcohols and hydroxides in open air
Wang, Zhi-Qin; Tang, Xiaosheng; Yang, Zhao-Qi; yu, baoyi; Wang, Hua-Jing; Sang, Wei; Yuan, Ye; Chen, Cheng; Verpoort, Francis; Chemical Communications  (2019) –; doi:10.1039/C9CC03519B

data_7123705
_publ_section_title
;
 Highly active bidentate N-heterocyclic carbene/ruthenium complexes
 performing dehydrogenative coupling of alcohols and hydroxides in open
 air
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/C9CC03519B
_journal_year                    2019
_chemical_formula_moiety         'C22 H23 I N2 Ru S'
_chemical_formula_sum            'C22 H23 I N2 Ru S'
_chemical_formula_weight         575.45
_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'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-01-18
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2016.11.30 svn.r3356 for OlexSys, GUI svn.r5269)
;
_audit_update_record
;
2019-04-23 deposited with the CCDC.    2019-06-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 104.9690(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.29220(10)
_cell_length_b                   12.56220(10)
_cell_length_c                   17.1913(2)
_cell_measurement_reflns_used    14737
_cell_measurement_temperature    298.15
_cell_measurement_theta_max      73.9940
_cell_measurement_theta_min      3.5130
_cell_volume                     2147.28(4)
_computing_cell_refinement       'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      298.15
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.9993
_diffrn_measured_fraction_theta_max 0.9797
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -35.00  89.00   0.50    0.50    --    0.00  77.00 -60.00  248
  2  \w    -35.00  89.00   0.50    0.50    --    0.00  77.00-120.00  248
  3  \w    -30.00  89.00   0.50    0.50    --    0.00  57.00  30.00  238
  4  \w      6.00 132.00   0.50    0.56    --   95.80 -30.00  90.00  252
  5  \w      6.00 133.00   0.50    0.56    --   95.80 -82.00   0.00  254
  6  \w     65.00 185.00   0.50    0.56    --   95.80  45.00  60.00  240
  7  \w     65.00 185.00   0.50    0.56    --   95.80  46.00 -78.57  240
  8  \w      6.00 126.00   0.50    0.56    --   95.80 -61.00   0.00  240
  9  \w      6.00 133.00   0.50    0.56    --   95.80 -82.00 -60.00  254
 10  \w      6.00 126.00   0.50    0.56    --   95.80 -61.00  60.00  240
 11  \w    -35.00  89.00   0.50    0.50    --    0.00  77.00-180.00  248
 12  \w    -32.00  89.00   0.50    0.50    --    0.00  38.00-180.00  242
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0082003000
_diffrn_orient_matrix_UB_12      -0.0065948000
_diffrn_orient_matrix_UB_13      0.0906177000
_diffrn_orient_matrix_UB_21      -0.1545684000
_diffrn_orient_matrix_UB_22      -0.0056884000
_diffrn_orient_matrix_UB_23      -0.0193850000
_diffrn_orient_matrix_UB_31      0.0068020000
_diffrn_orient_matrix_UB_32      -0.1223378000
_diffrn_orient_matrix_UB_33      -0.0040020000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0391
_diffrn_reflns_av_unetI/netI     0.0212
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            21148
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.207
_diffrn_reflns_theta_min         4.413
_diffrn_source                   'Rotating-anode X-ray tube (dual wavelength)'
_diffrn_source_type              'Rigaku (Cu) X-ray DW Source'
_exptl_absorpt_coefficient_mu    18.164
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.38874
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.33c (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.780
_exptl_crystal_description       block
_exptl_crystal_F_000             1128
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: CDCl3/pentane'
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.652
_refine_diff_density_min         -0.951
_refine_diff_density_rms         0.082
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     248
_refine_ls_number_reflns         4272
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0292
_refine_ls_R_factor_gt           0.0278
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0457P)^2^+1.2542P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0756
_refine_ls_wR_factor_ref         0.0766
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4013
_reflns_number_total             4272
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc03519b2.cif
_cod_data_source_block           54
_cod_database_code               7123705
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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:
 C9(H9)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C7(H7), C13(H13), C14(H14), C15(H15), C16(H16),
 C21(H21), C22(H22)
2.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C8(H8A,H8B,H8C), C10(H10A,H10B,H10C), C18(H18A,H18B,H18C)
;
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.264
_oxdiff_exptl_absorpt_empirical_full_min 0.740