Redox-Active N-Heterocyclic Carbenes: Design, Synthesis, and Evaluation of Their Electronic Properties
Rosen, Evelyn L.; Varnado, C. Daniel; Tennyson, Andrew G.; Khramov, Dimitri M.; Kamplain, Justin W.; Sung, Daphne H.; Cresswell, Philip T.; Lynch, Vincent M.; Bielawski, Christopher W.; Organometallics 28 (2009) 6695–; doi:10.1021/om900698x

data_4070286
_publ_section_title
;
 Redox-Active N-Heterocyclic Carbenes: Design, Synthesis, and Evaluation
 of Their Electronic Properties
;
_journal_issue                   23
_journal_name_full               Organometallics
_journal_page_first              6695
_journal_paper_doi               10.1021/om900698x
_journal_volume                  28
_journal_year                    2009
_chemical_formula_moiety
;
 C17 H12 N2 2-, C8 H12, 2 C5 H5 1-, 2 Fe 2+, 
 Ir 1+, Cl 1-, 2 C H Cl3
;
_chemical_formula_sum            'C37 H36 Cl7 Fe2 Ir N2'
_chemical_formula_weight         1060.73
_chemical_name_common            2a
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           62
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2n'
_symmetry_space_group_name_H-M   'P n m a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   19.6920(1)
_cell_length_b                   20.2716(3)
_cell_length_c                   9.4088(4)
_cell_measurement_reflns_used    4758
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      1
_cell_volume                     3755.88(17)
_computing_cell_refinement       'Collect software, Nonius B.V. 1998'
_computing_data_collection       'Collect software, Nonius B.V. 1998'
_computing_data_reduction
;
DENZO and Scalepack (Otwinoski and Minor, 1997)
;
_computing_molecular_graphics    'XP SHELXTL/PC, Siemens Analytical'
_computing_structure_refinement  'XL SHELXTL/PC, Siemens Analytical'
_computing_structure_solution
;

SIR97 - Altomare A., Burla M.C., Camalli M., Cascarano G.L., Giacovazzo C., 
Guagliardi A., Moliterni A.G.G., Polidori G.,Spagna R.
;
_diffrn_ambient_temperature      153(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       \w-scans
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71070
_diffrn_reflns_av_R_equivalents  0.0725
_diffrn_reflns_av_sigmaI/netI    0.0472
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            39719
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         2.01
_exptl_absorpt_coefficient_mu    4.826
_exptl_absorpt_correction_T_max  0.817
_exptl_absorpt_correction_T_min  0.467
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
 N.W. Alcock (1970). Cryst. Computing, p271
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.876
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needles
_exptl_crystal_F_000             2080
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.04
_refine_diff_density_max         1.642
_refine_diff_density_min         -0.621
_refine_diff_density_rms         0.129
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     247
_refine_ls_number_reflns         4417
_refine_ls_number_restraints     58
_refine_ls_restrained_S_all      1.076
_refine_ls_R_factor_all          0.0551
_refine_ls_R_factor_gt           0.0322
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0252P)^2^+6.6198P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0612
_refine_ls_wR_factor_ref         0.0682
_reflns_number_gt                3432
_reflns_number_total             4417
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om900698x_si_002.cif
_cod_data_source_block           benzfcir
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      Pnma
_cod_database_code               4070286