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_7123707
_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         'C21 H25 I N2 Ru'
_chemical_formula_sum            'C21 H25 I N2 Ru'
_chemical_formula_weight         533.40
_chemical_melting_point          440.8(6)
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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            16
_cell_length_a                   14.9258(2)
_cell_length_b                   19.4601(2)
_cell_length_c                   27.9272(4)
_cell_measurement_reflns_used    13954
_cell_measurement_temperature    120.0(1)
_cell_measurement_theta_max      74.2590
_cell_measurement_theta_min      3.1420
_cell_volume                     8111.67(18)
_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 0.997
_diffrn_measured_fraction_theta_max 0.972
_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    -29.00  33.00   0.50    0.50    --    0.00  57.00 120.00  124
  2  \w    -88.00 -26.00   0.50    0.50    --    0.00 -38.00  90.00  124
  3  \w     39.00  65.00   0.50    0.50    --    0.00  57.00 120.00   52
  4  \w     69.00 121.00   0.50    3.50    --   95.80 -77.00  30.00  104
  5  \w     19.00 119.00   0.50    3.50    --   95.80 -61.00-150.00  200
  6  \w     61.00 179.00   0.50    3.50    --   95.80  30.00  90.00  236
  7  \w     65.00 103.00   0.50    3.50    --   95.80  61.00-180.00   76
  8  \w     84.00 124.00   0.50    3.50    --   95.80 -45.00  90.00   80
  9  \w     31.00  63.00   0.50    3.50    --   95.80 -45.00  90.00   64
;
_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      -0.0247334000
_diffrn_orient_matrix_UB_12      -0.0628174000
_diffrn_orient_matrix_UB_13      0.0308228000
_diffrn_orient_matrix_UB_21      0.0232260000
_diffrn_orient_matrix_UB_22      -0.0479332000
_diffrn_orient_matrix_UB_23      -0.0420494000
_diffrn_orient_matrix_UB_31      0.0976169000
_diffrn_orient_matrix_UB_32      -0.0044398000
_diffrn_orient_matrix_UB_33      0.0178784000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0406
_diffrn_reflns_av_unetI/netI     0.0551
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            31417
_diffrn_reflns_point_group_measured_fraction_full 0.937
_diffrn_reflns_point_group_measured_fraction_max 0.894
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.386
_diffrn_reflns_theta_min         2.768
_diffrn_source                   'Rotating-anode X-ray tube (dual wavelength)'
_diffrn_source_type              'Rigaku (Cu) X-ray DW Source'
_exptl_absorpt_coefficient_mu    18.236
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.40590
_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    1.747
_exptl_crystal_description       block
_exptl_crystal_F_000             4192
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: CDCl3/n-pentane'
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_refine_diff_density_max         1.301
_refine_diff_density_min         -1.243
_refine_diff_density_rms         0.132
_refine_ls_abs_structure_details
;
 Flack x determined using 5105 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.009(4)
_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     921
_refine_ls_number_reflns         14816
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0425
_refine_ls_R_factor_gt           0.0381
_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^)+(0.0523P)^2^+7.4653P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0995
_refine_ls_wR_factor_ref         0.1016
_reflns_Friedel_coverage         0.687
_reflns_Friedel_fraction_full    0.864
_reflns_Friedel_fraction_max     0.800
_reflns_number_gt                13511
_reflns_number_total             14816
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc03519b2.cif
_cod_data_source_block           chen-wzq-166
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '440.15-441.35' was changed to
'440.8(6)' - 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               7123707
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.263
_shelx_estimated_absorpt_t_min   0.108
_reflns_odcompleteness_completeness 99.77
_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), C8A(H8AA), C8B(H8BA), C8C(H8CA)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C13(H13), C14(H14), C16(H16), C17(H17),
 C19(H19), C2A(H2A), C3A(H3A), C5A(H5A), C6A(H6A), C13A(H13A), C14A(H14A),
 C16A(H16A), C17A(H17A), C19A(H19A), C2B(H2B), C3B(H3B), C5B(H5B), C6B(H6B),
 C13B(H13B), C14B(H14B), C16B(H16B), C17B(H17B), C19B(H19B), C2C(H2C), C3C(H3C),
  C5C(H5C), C6C(H6C), C13C(H13C), C14C(H14C), C16C(H16C), C17C(H17C), C19C(H19C)
2.c Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C8(H8A,H8B,H8C), C10(H10A,H10B,H10C), C12(H12A,H12B,H12C),
 C21(H21A,H21B,H21C), C7A(H7AA,H7AB,H7AC), C9A(H9AA,H9AB,H9AC), C10A(H10D,H10E,
 H10F), C12A(H12D,H12E,H12F), C21A(H21D,H21E,H21F), C7B(H7BA,H7BB,H7BC),
 C9B(H9BA,H9BB,H9BC), C10B(H10G,H10H,H10I), C12B(H12G,H12H,H12I), C21B(H21G,
 H21H,H21I), C7C(H7CA,H7CB,H7CC), C9C(H9CA,H9CB,H9CC), C10C(H10J,H10K,H10L),
 C12C(H12J,H12K,H12L), C21C(H21J,H21K,H21L)
;
_shelx_res_checksum              65297
_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 2.098
_oxdiff_exptl_absorpt_empirical_full_min 0.618