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_4085638
_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         'C38 H43 Ag Cl N3'
_chemical_formula_sum            'C38 H43 Ag Cl N3'
_chemical_formula_weight         685.07
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           146
_symmetry_cell_setting           trigonal
_symmetry_space_group_name_Hall  'R 3'
_symmetry_space_group_name_H-M   'R 3 :H'
_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                120.00
_cell_formula_units_Z            18
_cell_length_a                   32.156(3)
_cell_length_b                   32.156(3)
_cell_length_c                   17.2446(16)
_cell_measurement_reflns_used    9914
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      26.18
_cell_measurement_theta_min      2.19
_cell_volume                     15442(2)
_computing_cell_refinement       'APEX2 Software Suite (Bruker, 2007)'
_computing_data_collection       'APEX2 Software Suite (Bruker, 2007)'
_computing_data_reduction        'APEX2 Software Suite (Bruker, 2007)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL and publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_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 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0437
_diffrn_reflns_av_sigmaI/netI    0.0330
_diffrn_reflns_limit_h_max       38
_diffrn_reflns_limit_h_min       -38
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_k_min       -38
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            82187
_diffrn_reflns_theta_full        25.24
_diffrn_reflns_theta_max         25.24
_diffrn_reflns_theta_min         1.39
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.695
_exptl_absorpt_correction_T_max  0.9338
_exptl_absorpt_correction_T_min  0.7226
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
program SADABS, Bruker (2001).
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.326
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             6408
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.10
_refine_diff_density_max         1.134
_refine_diff_density_min         -0.586
_refine_diff_density_rms         0.080
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.02(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           fullcycle
_refine_ls_number_parameters     787
_refine_ls_number_reflns         11995
_refine_ls_number_restraints     90
_refine_ls_restrained_S_all      1.099
_refine_ls_R_factor_all          0.0555
_refine_ls_R_factor_gt           0.0439
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0714P)^2^+35.3296P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1135
_refine_ls_wR_factor_ref         0.1201
_reflns_number_gt                10352
_reflns_number_total             11995
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om5b00046_si_001.cif
_cod_data_source_block           8h
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Trigonal' changed to 'trigonal'
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_original_sg_symbol_H-M      'R 3'
_cod_database_code               4085638