Chiral, Sterically Demanding N-Heterocyclic Carbenes Fused into a Heterobiaryl Skeleton: Design, Synthesis, and Structural Analysis
Espina, Manuela; Rivilla, Ivan; Conde, Ana; Díaz-Requejo, M. Mar; Pérez, Pedro J.; Álvarez, Eleuterio; Fernández, Rosario; Lassaletta, José M.; Organometallics  (2015) 150320082744001–; doi:10.1021/acs.organomet.5b00046

data_4085639
_publ_section_title
;
 Chiral, Sterically Demanding N-Heterocyclic Carbenes Fused into a
 Heterobiaryl Skeleton: Design, Synthesis, and Structural Analysis
;
_journal_name_full               Organometallics
_journal_page_first              150320082744001
_journal_paper_doi               10.1021/acs.organomet.5b00046
_journal_year                    2015
_chemical_absolute_configuration rmad
_chemical_formula_moiety         '2(C29 H24 Au Cl F N3), C H2 Cl2, 3(H2 O)'
_chemical_formula_sum            'C29.5 H28 Au Cl2 F N3 O1.5'
_chemical_formula_weight         735.41
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_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     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            8
_cell_length_a                   13.7911(17)
_cell_length_b                   19.584(3)
_cell_length_c                   22.609(3)
_cell_measurement_reflns_used    9907
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      23.08
_cell_measurement_theta_min      2.33
_cell_volume                     6106.3(14)
_computing_cell_refinement       'APEX2 Software Suite'
_computing_data_collection       'APEX2 Software Suite (Bruker, 2005)'
_computing_data_reduction        'APEX2 Software Suite'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 1997b)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997a)'
_computing_structure_solution    'SIR2002 (Burla et al., 2003)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 8.26
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type
; 
 Bruker-Nonius X8kappa APEX II CCD area detector 
;
_diffrn_measurement_method       'phi and omega scans with narrow frames'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0931
_diffrn_reflns_av_sigmaI/netI    0.1162
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            72611
_diffrn_reflns_theta_full        30.51
_diffrn_reflns_theta_max         30.51
_diffrn_reflns_theta_min         1.73
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    5.027
_exptl_absorpt_correction_T_max  0.4501
_exptl_absorpt_correction_T_min  0.3663
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
 APEX2 Software Suite; Bruker 2005. 
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.600
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             2880
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_refine_diff_density_max         1.877
_refine_diff_density_min         -1.739
_refine_diff_density_rms         0.192
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.004(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     685
_refine_ls_number_reflns         17622
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.1389
_refine_ls_R_factor_gt           0.0583
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0865P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1384
_refine_ls_wR_factor_ref         0.1742
_reflns_number_gt                9802
_reflns_number_total             17622
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om5b00046_si_001.cif
_cod_data_source_block           9b
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 3105 2015-03-04 15:46:00Z robertas 
;
_cod_database_code               4085639