A Pyrene-Based N-Heterocyclic Carbene: Study of Its Coordination Chemistry and Stereoelectronic Properties
Valdés, Hugo; Poyatos, Macarena; Peris, Eduardo; Organometallics 33 (2014) 394–; doi:10.1021/om401134w

data_4082532
_publ_section_title
;
 A Pyrene-Based N-Heterocyclic Carbene: Study of Its Coordination
 Chemistry and Stereoelectronic Properties
;
_journal_issue                   1
_journal_name_full               Organometallics
_journal_page_first              394
_journal_paper_doi               10.1021/om401134w
_journal_volume                  33
_journal_year                    2014
_chemical_formula_moiety         'C43 H53 Br Ir N2 Ru, F6 P'
_chemical_formula_sum            'C43 H53 Br F6 Ir N2 P Ru'
_chemical_formula_weight         1116.02
_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
_atom_sites_solution_primary     direct
_audit_creation_date             2013-11-13
_audit_creation_method
;
  Olex2 1.2
  (compiled Apr 23 2013 17:59:47, GUI svn.r4466)
;
_cell_angle_alpha                96.493(3)
_cell_angle_beta                 101.866(2)
_cell_angle_gamma                118.496(3)
_cell_formula_units_Z            2
_cell_length_a                   11.8980(3)
_cell_length_b                   12.2223(4)
_cell_length_c                   17.2260(4)
_cell_measurement_reflns_used    14046
_cell_measurement_temperature    200.1(2)
_cell_measurement_theta_max      28.4980
_cell_measurement_theta_min      3.4520
_cell_volume                     2088.54(13)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      200.1(2)
_diffrn_detector_area_resol_mean 10.4051
_diffrn_measured_fraction_theta_full 0.9986
_diffrn_measured_fraction_theta_max 0.8505
_diffrn_measurement_details
;
  1 omega  -20.00   26.00   0.5000   22.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.1253  -99.0000   30.0000 92

  2 omega   -2.00   82.00   0.5000   22.0000
omega____ theta____ kappa____ phi______ frames
    -       12.3753   38.0000  -60.0000 168

  3 omega   16.00   72.00   0.5000   22.0000
omega____ theta____ kappa____ phi______ frames
    -       12.3753 -143.0000  131.0287 112

  4 omega    7.00   88.00   0.5000   22.0000
omega____ theta____ kappa____ phi______ frames
    -       12.3753   38.0000    0.0000 162

  5 omega  -36.00   43.00   0.5000   22.0000
omega____ theta____ kappa____ phi______ frames
    -       12.3753  -77.0000 -180.0000 158

  6 omega -100.00  -55.00   0.5000   22.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.1253  178.0000 -150.0000 90

  7 omega  -20.00   54.00   0.5000   22.0000
omega____ theta____ kappa____ phi______ frames
    -       12.3753  -99.0000   60.0000 148

  8 omega  -64.00   39.00   0.5000   22.0000
omega____ theta____ kappa____ phi______ frames
    -       12.3753  -38.0000 -150.0000 206

  9 omega  -17.00   86.00   0.5000   22.0000
omega____ theta____ kappa____ phi______ frames
    -       12.3753   57.0000    0.0000 206

 10 omega  -14.00   88.00   0.5000   22.0000
omega____ theta____ kappa____ phi______ frames
    -       12.3753   38.0000 -150.0000 204

 11 omega    2.00   49.00   0.5000   22.0000
omega____ theta____ kappa____ phi______ frames
    -       12.3753 -125.0000  161.8869 94

 12 omega   53.00   89.00   0.5000   22.0000
omega____ theta____ kappa____ phi______ frames
    -       12.3753  155.0000   29.2968 72
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0024177000
_diffrn_orient_matrix_UB_12      -0.0095036000
_diffrn_orient_matrix_UB_13      0.0400364000
_diffrn_orient_matrix_UB_21      0.0483717000
_diffrn_orient_matrix_UB_22      0.0661476000
_diffrn_orient_matrix_UB_23      0.0167627000
_diffrn_orient_matrix_UB_31      -0.0519779000
_diffrn_orient_matrix_UB_32      0.0132054000
_diffrn_orient_matrix_UB_33      -0.0001741000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0519
_diffrn_reflns_av_unetI/netI     0.0492
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.912
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            45967
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.912
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.525
_diffrn_reflns_theta_min         2.712
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    4.599
_exptl_absorpt_correction_T_max  0.995
_exptl_absorpt_correction_T_min  0.985
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
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
;
;
_exptl_crystal_density_diffrn    1.775
_exptl_crystal_description
;
;
_exptl_crystal_F_000             1100
_exptl_crystal_size_max          0.1472
_exptl_crystal_size_mid          0.1353
_exptl_crystal_size_min          0.0549
_refine_diff_density_max         2.395
_refine_diff_density_min         -1.419
_refine_diff_density_rms         0.154
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     512
_refine_ls_number_reflns         10643
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.082
_refine_ls_R_factor_all          0.0753
_refine_ls_R_factor_gt           0.0433
_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^)+(0.0332P)^2^+8.8539P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0890
_refine_ls_wR_factor_ref         0.1069
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7945
_reflns_number_total             10643
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            om401134w_si_002.cif
_cod_data_source_block           of_9b_(str1556)
_cod_original_cell_volume        2088.52(12)
_cod_database_code               4082532
_chemical_oxdiff_formula         'C33 H53 N2 Cl Ir Ru P F6'
_reflns_odcompleteness_completeness 99.86
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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. Others
 Fixed Sof: F6(0.5) F6A(0.5)
3.a Ternary CH refined with riding coordinates:
 C33(H33), C30(H30), C15(H15), C13(H13), C14(H14), C29(H29), C26(H26)
3.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C2(H2A,H2B), C3(H3A,H3B), C7(H7A,H7B), C8(H8A,H8B), C31(H31A,
 H31B), C28(H28A,H28B), C32(H32A,H32B), C27(H27A,H27B), C4(H4A,H4B)
3.c Aromatic/amide H refined with riding coordinates:
 C17(H17), C18(H18), C22(H22), C21(H21), C20(H20)
3.d Idealised Me refined as rotating group:
 C40(H40A,H40B,H40C), C41(H41A,H41B,H41C), C42(H42A,H42B,H42C), C43(H43A,H43B,
 H43C), C39(H39A,H39B,H39C), C9(H9A,H9B,H9C), C5(H5A,H5B,H5C)
;
_shelx_hkl_checksum              6987
_shelx_res_checksum              20661
_shelxl_version_number           2013-4