Synthesis of Hemilabile Cyclic (Alkyl)(amino)carbenes (CAACs) and Applications in Organometallic Chemistry.
Chu, Jiaxiang; Munz, Dominik; Jazzar, Rodolphe; Melaimi, Mohand; Bertrand, Guy; Journal of the American Chemical Society 138 (2016) 7884–7887; doi:10.1021/jacs.6b05221

data_4125108
_publ_section_title
;
 Synthesis of Hemilabile Cyclic (Alkyl)(amino)carbenes (CAACs) and
 Applications in Organometallic Chemistry.
;
_journal_issue                   25
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              7884
_journal_page_last               7887
_journal_paper_doi               10.1021/jacs.6b05221
_journal_volume                  138
_journal_year                    2016
_chemical_formula_moiety         'C48 H62 Au N2, B C24 F20, C6 H6'
_chemical_formula_sum            'C78 H68 Au B F20 N2'
_chemical_formula_weight         1621.12
_chemical_name_systematic        ImineCAACPdBiphenyl
_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             2016-05-10
_audit_creation_method
;
Olex2 1.2
(compiled Jan 19 2015 12:28:14 for OlexSys, GUI svn.r4998)
;
_cell_angle_alpha                88.698(2)
_cell_angle_beta                 87.417(2)
_cell_angle_gamma                82.569(2)
_cell_formula_units_Z            2
_cell_length_a                   13.7142(5)
_cell_length_b                   15.7707(7)
_cell_length_c                   15.8385(7)
_cell_measurement_reflns_used    9735
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      23.34
_cell_measurement_theta_min      2.21
_cell_volume                     3392.9(2)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'APEX2 v2013.6-2 (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'Bruker APEX CCD'
_diffrn_detector_area_resol_mean 8.0
_diffrn_detector_type            'CCD Area Detector'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       'Kappa Four-Circle Diffractometer'
_diffrn_measurement_device_type  'Bruker X8 APEX'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0583
_diffrn_reflns_av_unetI/netI     0.0555
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            54719
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.452
_diffrn_reflns_theta_max         25.452
_diffrn_reflns_theta_min         2.209
_diffrn_source                   'sealed tube'
_diffrn_source_type              fine-focus
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.270
_exptl_absorpt_correction_T_max  0.0916
_exptl_absorpt_correction_T_min  0.0580
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014) was used for absorption correction.
wR2(int) was 0.0798 before and 0.0565 after correction.
The Ratio of minimum to maximum transmission is 0.6332.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.587
_exptl_crystal_description       block
_exptl_crystal_F_000             1628
_exptl_crystal_preparation       'Fomblin oil'
_exptl_crystal_recrystallization_method Benzene/Pentane
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.726
_refine_diff_density_min         -0.783
_refine_diff_density_rms         0.090
_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     933
_refine_ls_number_reflns         12513
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.013
_refine_ls_R_factor_all          0.0446
_refine_ls_R_factor_gt           0.0311
_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^)+(0.0221P)^2^+1.5912P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0586
_refine_ls_wR_factor_ref         0.0628
_reflns_Friedel_coverage         0.000
_reflns_number_gt                10466
_reflns_number_total             12513
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja6b05221_si_005.cif
_cod_data_source_block           iminecaacpdbiphenyl
_cod_depositor_comments
;
The following automatic conversions were performed:

'_diffrn_radiation_probe' value 'X-ray' changed to 'x-ray' 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 4268 2015-11-12 08:31:59Z antanas 

 Adding full bibliography for 4125107--4125110.cif.
;
_cod_database_code               4125108
_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.a Ternary CH refined with riding coordinates:
 C46(H46), C31(H31), C34(H34), C43(H43)
2.b Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B)
2.c Aromatic/amide H refined with riding coordinates:
 C11(H11), C2(H2), C29(H29), C27(H27), C10(H10), C5(H5), C41(H41), C9(H9),
 C8(H8), C28(H28), C3(H3), C4(H4), C39(H39), C40(H40), C2B(H2B), C3B(H3B),
 C4B(H4B), C5B(H5B), C6B(H6B), C1B(H1B)
2.d Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C19(H19A,H19B,H19C), C17(H17A,H17B,H17C), C22(H22A,H22B,
 H22C), C23(H23A,H23B,H23C), C24(H24A,H24B,H24C), C48(H48A,H48B,H48C), C33(H33A,
 H33B,H33C), C35(H35A,H35B,H35C), C44(H44A,H44B,H44C), C45(H45A,H45B,H45C),
 C32(H32A,H32B,H32C), C36(H36A,H36B,H36C), C47(H47A,H47B,H47C)
;
_shelx_res_checksum              19706
_shelx_hkl_checksum              19134
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'