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_7123708
_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         'C20 H22 I N3 O2 Ru, C D Cl3'
_chemical_formula_sum            'C21 H22 Cl3 D I N3 O2 Ru'
_chemical_formula_weight         684.75
_chemical_melting_point          502.7(7)
_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     dual
_audit_creation_date             2019-06-14
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2016.11.30 svn.r3356 for OlexSys, GUI svn.r5269)
;
_audit_update_record
;
2019-06-16 deposited with the CCDC.    2019-06-20 downloaded from the CCDC.
;
_cell_angle_alpha                69.440(2)
_cell_angle_beta                 86.519(2)
_cell_angle_gamma                76.073(2)
_cell_formula_units_Z            2
_cell_length_a                   7.7867(2)
_cell_length_b                   11.3713(2)
_cell_length_c                   14.9139(3)
_cell_measurement_reflns_used    7518
_cell_measurement_temperature    120.0(1)
_cell_measurement_theta_max      74.0980
_cell_measurement_theta_min      4.3180
_cell_volume                     1199.68(5)
_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_environment      N~2~
_diffrn_ambient_temperature      120.0(1)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.9951
_diffrn_measured_fraction_theta_max 0.9593
_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    -88.00  29.00   0.50    0.50    --    0.00 -57.00  90.00  234
  2  \w    -14.00  28.00   0.50    0.50    --    0.00 -57.00-180.00   84
  3  \w    -79.00 -35.00   0.50    0.50    --    0.00 -57.00   0.00   88
  4  \w     -1.00  82.00   0.50    0.50    --    0.00  38.00  60.00  166
  5  \w    -83.00 -57.00   0.50    0.50    --    0.00 -57.00-180.00   52
  6  \w     10.00 132.00   0.50    0.50    --   95.80 -30.00 150.00  244
  7  \w     49.00 133.00   0.50    0.50    --   95.80 -82.00  60.00  168
  8  \w     63.00  89.00   0.50    0.50    --   95.80  30.00   0.00   52
  9  \w     76.00 154.00   0.50    0.50    --   95.80  30.00 150.00  156
 10  \w     11.00  44.00   0.50    0.50    --   95.80 -82.00  60.00   66
 11  \w     44.00  78.00   0.50    0.50    --   95.80 -82.00   0.00   68
 12  \w     81.00 106.00   0.50    0.50    --   95.80 -82.00   0.00   50
 13  \w     92.00 118.00   0.50    0.50    --   95.80 -82.00 120.00   52
 14  \w      8.00  34.00   0.50    0.50    --   95.80 -45.00 -60.00   52
 15  \w     10.00 121.00   0.50    0.50    --   95.80 -82.00-120.00  222
 16  \w     94.00 185.00   0.50    0.50    --   95.80  30.00 120.00  182
 17  \w     62.00 111.00   0.50    0.50    --   95.80 -45.00 -60.00   98
 18  \w    100.00 174.00   0.50    0.50    --   95.80  30.00   0.00  148
 19  \w     92.00 132.00   0.50    0.50    --   95.80 -82.00 -60.00   80
 20  \w     96.00 122.00   0.50    0.50    --   95.80  61.00-180.00   52
 21  \w     32.00 125.00   0.50    0.50    --   95.80 -61.00-120.00  186
 22  \w     11.00 120.00   0.50    0.50    --   95.80 -61.00  60.00  218
;
_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      0.0078696000
_diffrn_orient_matrix_UB_12      -0.1336930000
_diffrn_orient_matrix_UB_13      0.0771172000
_diffrn_orient_matrix_UB_21      -0.0997694000
_diffrn_orient_matrix_UB_22      0.0653985000
_diffrn_orient_matrix_UB_23      0.0688781000
_diffrn_orient_matrix_UB_31      -0.1776590000
_diffrn_orient_matrix_UB_32      -0.0025465000
_diffrn_orient_matrix_UB_33      -0.0385825000
_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  0.0315
_diffrn_reflns_av_unetI/netI     0.0393
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.958
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            12444
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.958
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.218
_diffrn_reflns_theta_min         3.166
_diffrn_source                   'Rotating-anode X-ray tube (dual wavelength)'
_diffrn_source_type              'Rigaku (Cu) X-ray DW Source'
_exptl_absorpt_coefficient_mu    18.663
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.45259
_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            'brownish red'
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.896
_exptl_crystal_description       block
_exptl_crystal_F_000             668
_exptl_crystal_preparation       hadd
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: CDCl3/n-pentane'
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.1
_refine_diff_density_max         1.642
_refine_diff_density_min         -1.211
_refine_diff_density_rms         0.121
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     288
_refine_ls_number_reflns         4681
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.086
_refine_ls_R_factor_all          0.0356
_refine_ls_R_factor_gt           0.0333
_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^)+(0.0417P)^2^+2.2171P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0867
_refine_ls_wR_factor_ref         0.0879
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4309
_reflns_number_total             4681
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc03519b2.cif
_cod_data_source_block           chen-wzq-169
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '502.05-503.35' was changed to
'502.7(7)' - the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 
;
_cod_database_code               7123708
_shelx_estimated_absorpt_t_max   0.257
_shelx_estimated_absorpt_t_min   0.118
_reflns_odcompleteness_completeness 99.51
_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. Uiso/Uaniso restraints and constraints
Uanis(I1A) = Uanis(I1)
3. Others
 Sof(I1A)=1-FVAR(1)
 Sof(I1)=FVAR(1)
4.a Ternary CH refined with riding coordinates:
 C8(H8), C21(D21)
4.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C12(H12), C13(H13), C16(H16), C18(H18),
 C19(H19)
4.c Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C9(H9A,H9B,H9C), C10(H10A,H10B,H10C), C20(H20A,H20B,H20C)
;
_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 2.084
_oxdiff_exptl_absorpt_empirical_full_min 0.708