Synthesis and catalytic activity of ruthenium indenylidene complexes bearing unsymmetrical NHC containing a heteroaromatic moiety
Smoleń, Michał; Kosnik, Wioletta; Loska, Rafał; Gajda, Roman; Malinska, Maura; Wozniak, Krzysztof; Grela, Karol; RSC Adv.  (2016) –; doi:10.1039/C6RA18210K

data_7226200
_publ_section_title
;
 Synthesis and catalytic activity of ruthenium indenylidene complexes
 bearing unsymmetrical NHC containing a heteroaromatic moiety
;
_journal_name_full               'RSC Adv.'
_journal_paper_doi               10.1039/C6RA18210K
_journal_year                    2016
_chemical_formula_moiety         'C27 H32 Cl2 N2 O Ru S'
_chemical_formula_sum            'C27 H32 Cl2 N2 O Ru S'
_chemical_formula_weight         604.57
_chemical_name_systematic
;
 ?
;
_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
_audit_creation_date             2016-02-16
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_audit_update_record
;
2016-02-16 deposited with the CCDC.
2016-08-08 downloaded from the CCDC.
;
_cell_angle_alpha                85.6667(14)
_cell_angle_beta                 88.7614(16)
_cell_angle_gamma                89.6770(17)
_cell_formula_units_Z            8
_cell_length_a                   10.5766(2)
_cell_length_b                   15.0612(3)
_cell_length_c                   34.1951(6)
_cell_measurement_reflns_used    34203
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      32.0400
_cell_measurement_theta_min      2.0030
_cell_volume                     5430.27(18)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean 16.0026
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.958
_diffrn_measurement_details
;
  1 omega   36.00   95.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       -0.0391  178.0000 -120.0000 59

  2 omega  -77.00   -6.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       -0.0391  -57.0000  -60.0000 71

  3 omega   35.00   65.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       -0.0391   57.0000 -120.0000 30

  4 omega    2.00   38.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       -0.0391  -57.0000  -60.0000 36

  5 omega   91.00  122.00   1.0000   26.0000
omega____ theta____ kappa____ phi______ frames
    -       39.1675  125.0000  -30.0000 31

  6 omega    1.00   96.00   1.0000   26.0000
omega____ theta____ kappa____ phi______ frames
    -       39.1675  -99.0000  150.0000 95

  7 omega   -3.00   93.00   1.0000   26.0000
omega____ theta____ kappa____ phi______ frames
    -       39.1675  -99.0000    0.0000 96

  8 omega -116.00  -90.00   1.0000   26.0000
omega____ theta____ kappa____ phi______ frames
    -      -39.2456 -125.0000 -120.0000 26

  9 omega -116.00  -90.00   1.0000   26.0000
omega____ theta____ kappa____ phi______ frames
    -      -39.2456 -125.0000   30.0000 26

 10 omega -122.00  -91.00   1.0000   26.0000
omega____ theta____ kappa____ phi______ frames
    -      -39.2456 -125.0000  -30.0000 31

 11 omega  -66.00  -13.00   1.0000   26.0000
omega____ theta____ kappa____ phi______ frames
    -      -39.2456  125.0000 -120.0000 53

 12 omega -117.00  -91.00   1.0000   26.0000
omega____ theta____ kappa____ phi______ frames
    -      -39.2456 -125.0000  120.0000 26

 13 omega  -43.00  -12.00   1.0000   26.0000
omega____ theta____ kappa____ phi______ frames
    -      -39.2456  125.0000    0.0000 31

 14 omega -129.00   53.00   1.0000   26.0000
omega____ theta____ kappa____ phi______ frames
    -      -39.2456    0.0000    0.0000 182

 15 omega   35.00   97.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       -0.0391  178.0000  120.0000 62

 16 omega  -78.00   42.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       -0.0391  -57.0000    0.0000 120

 17 omega  -46.00   88.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       -0.0391   77.0000  -30.0000 134

 18 omega   -3.00  117.00   1.0000   26.0000
omega____ theta____ kappa____ phi______ frames
    -       39.1675   57.0000 -180.0000 120

 19 omega   -3.00  117.00   1.0000   26.0000
omega____ theta____ kappa____ phi______ frames
    -       39.1675   57.0000  -90.0000 120

 20 omega -130.00  -79.00   1.0000   26.0000
omega____ theta____ kappa____ phi______ frames
    -      -39.2456  -99.0000  -90.0000 51

 21 omega -128.00    6.00   1.0000   26.0000
omega____ theta____ kappa____ phi______ frames
    -      -39.2456  -77.0000    0.0000 134

 22 omega -128.00  -11.00   1.0000   26.0000
omega____ theta____ kappa____ phi______ frames
    -      -39.2456  -77.0000   90.0000 117

 23 omega -128.00    6.00   1.0000   26.0000
omega____ theta____ kappa____ phi______ frames
    -      -39.2456  -77.0000  -90.0000 134
;
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0467611000
_diffrn_orient_matrix_UB_12      -0.0337216000
_diffrn_orient_matrix_UB_13      0.0011040000
_diffrn_orient_matrix_UB_21      0.0401524000
_diffrn_orient_matrix_UB_22      -0.0281726000
_diffrn_orient_matrix_UB_23      0.0118153000
_diffrn_orient_matrix_UB_31      -0.0264727000
_diffrn_orient_matrix_UB_32      0.0173157000
_diffrn_orient_matrix_UB_33      0.0170912000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0734
_diffrn_reflns_av_unetI/netI     0.0874
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.958
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       51
_diffrn_reflns_limit_l_min       -51
_diffrn_reflns_number            146961
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.958
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         32.669
_diffrn_reflns_theta_min         1.738
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.874
_exptl_absorpt_correction_T_max  0.954
_exptl_absorpt_correction_T_min  0.934
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Analytical numeric absorption correction using a multifaceted crystal
            model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_crystal_colour            brown
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.479
_exptl_crystal_description       block
_exptl_crystal_F_000             2480
_exptl_crystal_size_max          0.1134
_exptl_crystal_size_mid          0.0855
_exptl_crystal_size_min          0.0733
_refine_diff_density_max         1.342
_refine_diff_density_min         -1.102
_refine_diff_density_rms         0.157
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1277
_refine_ls_number_reflns         38148
_refine_ls_number_restraints     132
_refine_ls_restrained_S_all      1.081
_refine_ls_R_factor_all          0.0935
_refine_ls_R_factor_gt           0.0581
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[\s^2^(Fo^2^)+(0.0221P)^2^+21.7261P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1186
_refine_ls_wR_factor_ref         0.1325
_reflns_Friedel_coverage         0.000
_reflns_number_gt                26876
_reflns_number_total             38148
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6ra18210k2.cif
_cod_data_source_block           7
_cod_database_code               7226200
_shelxl_version_number           2013-2
_chemical_oxdiff_formula         'Ru1 Cl2 N2 O1 S1 C27 H32'
_reflns_odcompleteness_completeness 99.99
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     30.93
_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. Restrained planarity
 S1A, C21, C22A, C24A, C23A
 with sigma of 0.1
 S1B, C21, C22B, C24B, C23B
 with sigma of 0.1
3. Rigid bond restraints
 C21, C22A, C24A, C23A, C22B, C24B, C23B
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
C21 \\sim C22A \\sim C24A \\sim C23A \\sim C22B \\sim C24B \\sim C23B: within
1.7A with sigma of 0.04 and sigma for terminal atoms of 0.08
Uanis(C21) \\sim Ueq, Uanis(C22A) \\sim Ueq, Uanis(C23A) \\sim Ueq, Uanis(C22B)
\\sim Ueq, Uanis(C24B) \\sim Ueq, Uanis(C23B) \\sim Ueq: with sigma of 0.1 and
sigma for terminal atoms of 0.2
5. Same fragment restrains
{C20, C21, S1B, C22B, C24B, C23B} sigma for 1-2: 0.02, 1-3: 0.04
as
{C20, C21, S1A, C22A, C24A, C23A}
6. Others
 Sof(S1B)=Sof(C22B)=Sof(H22B)=Sof(C24B)=Sof(H24B)=Sof(C23B)=Sof(H23B)=1-FVAR(1)
 Sof(S1A)=Sof(C22A)=Sof(H22A)=Sof(C24A)=Sof(H24A)=Sof(C23A)=Sof(H23A)=FVAR(1)
7.a Ternary CH refined with riding coordinates:
 C17(H17), C47(H47), C77(H77), C107(H107)
7.b Secondary CH2 refined with riding coordinates:
 C20(H20A,H20B), C2(H2A,H2B), C3(H3A,H3B), C32(H32A,H32B), C33(H33A,H33B),
 C50(H50A,H50B), C63(H63A,H63B), C62(H62A,H62B), C80(H80A,H80B), C92(H92A,H92B),
  C93(H93A,H93B), C110(H11A,H11B)
7.c Aromatic/amide H refined with riding coordinates:
 C22A(H22A), C24A(H24A), C23A(H23A), C22B(H22B), C24B(H24B), C23B(H23B),
 C10(H10), C12(H12), C13(H13), C14(H14), C15(H15), C6(H6), C8(H8), C40(H40),
 C42(H42), C43(H43), C44(H44), C45(H45), C36(H36), C38(H38), C52(H52), C53(H53),
  C54(H54), C70(H70), C72(H72), C73(H73), C74(H74), C75(H75), C66(H66),
 C68(H68), C82(H82), C83(H83), C84(H84), C100(H100), C102(H102), C103(H103),
 C104(H104), C105(H105), C96(H96), C98(H98), C112(H112), C113(H113), C114(H114)
7.d Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C19(H19A,H19B,H19C), C9A(H9AA,H9AB,H9AC), C5A(H5AA,H5AB,
 H5AC), C7A(H7AA,H7AB,H7AC), C48(H48A,H48B,H48C), C49(H49A,H49B,H49C),
 C39A(H39A,H39B,H39C), C35A(H35A,H35B,H35C), C37A(H37A,H37B,H37C), C79(H79A,
 H79B,H79C), C78(H78A,H78B,H78C), C69A(H69A,H69B,H69C), C65A(H65A,H65B,H65C),
 C67A(H67A,H67B,H67C), C108(H10A,H10B,H10C), C109(H10D,H10E,H10F), C99A(H99A,
 H99B,H99C), C95A(H95A,H95B,H95C), C97A(H97A,H97B,H97C)
;
_shelx_res_checksum              25127
_olex2_submission_special_instructions 'No special instructions were received'