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_7123706
_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 H27 I N2 Ru'
_chemical_formula_sum            'C22 H27 I N2 Ru'
_chemical_formula_weight         547.42
_chemical_melting_point          471.0(8)
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-06-08
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-06-14 deposited with the CCDC.    2019-06-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   14.2389(2)
_cell_length_b                   7.8105(2)
_cell_length_c                   38.0164(7)
_cell_measurement_reflns_used    6594
_cell_measurement_temperature    120.0(1)
_cell_measurement_theta_max      73.7260
_cell_measurement_theta_min      4.6580
_cell_volume                     4227.92(15)
_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 0.999
_diffrn_measured_fraction_theta_max 0.970
_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    -42.00   8.00   0.50    0.50    --    0.00 -57.00 150.00  100
  2  \w    -31.00  81.00   0.50    0.50    --    0.00  77.00-180.00  224
  3  \w     76.00 103.00   0.50    1.00    --   95.80  61.00 -60.00   54
  4  \w     59.00 112.00   0.50    1.00    --   95.80 -82.00  60.00  106
  5  \w      9.00  42.00   0.50    1.00    --   95.80 -82.00  60.00   66
  6  \w    152.00 178.00   0.50    1.00    --   95.80  61.00 -60.00   52
  7  \w     19.00 129.00   0.50    1.00    --   95.80 -30.00 -90.00  220
  8  \w     11.00 106.00   0.50    1.00    --   95.80 -61.00  60.00  190
;
_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      -0.0617520000
_diffrn_orient_matrix_UB_12      0.0324748000
_diffrn_orient_matrix_UB_13      0.0326115000
_diffrn_orient_matrix_UB_21      -0.0888515000
_diffrn_orient_matrix_UB_22      -0.0224893000
_diffrn_orient_matrix_UB_23      -0.0226245000
_diffrn_orient_matrix_UB_31      -0.0000761000
_diffrn_orient_matrix_UB_32      -0.1932609000
_diffrn_orient_matrix_UB_33      0.0081374000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0482
_diffrn_reflns_av_unetI/netI     0.0497
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       47
_diffrn_reflns_limit_l_min       -45
_diffrn_reflns_number            14081
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.371
_diffrn_reflns_theta_min         3.879
_diffrn_source                   'Rotating-anode X-ray tube (dual wavelength)'
_diffrn_source_type              'Rigaku (Cu) X-ray DW Source'
_exptl_absorpt_coefficient_mu    17.511
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.43764
_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            'Light yellow'
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.720
_exptl_crystal_description       block
_exptl_crystal_F_000             2160
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: CDCl3/n-pentane'
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.881
_refine_diff_density_min         -0.942
_refine_diff_density_rms         0.144
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     240
_refine_ls_number_reflns         4186
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0399
_refine_ls_R_factor_gt           0.0366
_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^)+(0.0437P)^2^+8.2614P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0935
_refine_ls_wR_factor_ref         0.0953
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3809
_reflns_number_total             4186
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc03519b2.cif
_cod_data_source_block           chen-wzq-167
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '470.25-471.75' was changed to
'471.0(8)' - 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               7123706
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.273
_shelx_estimated_absorpt_t_min   0.107
_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:
 C8(H8), C20(H20)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C7(H7), C12(H12), C13(H13), C14(H14), C15(H15),
 C18(H18), C19(H19)
2.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C9(H9A,H9B,H9C), C10(H10A,H10B,H10C), C21(H21A,H21B,H21C),
 C22(H22A,H22B,H22C)
;
_shelx_res_checksum              72240
_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 1.825
_oxdiff_exptl_absorpt_empirical_full_min 0.602