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_4125109
_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         'C36 H54 Au Cl N2'
_chemical_formula_sum            'C36 H54 Au Cl N2'
_chemical_formula_weight         747.23
_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-beta
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_cell_angle_alpha                106.828(2)
_cell_angle_beta                 94.902(2)
_cell_angle_gamma                98.618(2)
_cell_formula_units_Z            4
_cell_length_a                   10.0911(7)
_cell_length_b                   18.5601(14)
_cell_length_c                   19.6959(14)
_cell_measurement_reflns_used    7398
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.32
_cell_measurement_theta_min      2.18
_cell_volume                     3458.6(4)
_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, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'Bruker APEX-II CCD'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD Area Detector'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device       'Kappa Four-Circle Diffractometer'
_diffrn_measurement_device_type  'Bruker APEX II Ultra'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'Double Bounce Multilayer Mirrors'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_unetI/netI     0.0710
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            16395
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.415
_diffrn_reflns_theta_min         1.090
_diffrn_source                   'Micro Focus Rotating Anode'
_diffrn_source_type              'Bruker TXS'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    4.356
_exptl_absorpt_correction_T_max  0.096
_exptl_absorpt_correction_T_min  0.061
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 TWINABS-2012/1 (Bruker,2012) was used for absorption correction.
 
For component 1:
 wR2(int) was 0.0557 before and 0.0366 after correction.
 The Ratio of minimum to maximum transmission not present.
 The \l/2 correction factor is Not present
 
For component 2:
 wR2(int) was 0.0677 before and 0.0354 after correction.
 The Ratio of minimum to maximum transmission not present.
 The \l/2 correction factor is Not present
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.435
_exptl_crystal_description       plate
_exptl_crystal_F_000             1520
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.01
_refine_diff_density_max         1.485
_refine_diff_density_min         -0.908
_refine_diff_density_rms         0.153
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     738
_refine_ls_number_reflns         16395
_refine_ls_number_restraints     30
_refine_ls_restrained_S_all      1.018
_refine_ls_R_factor_all          0.0718
_refine_ls_R_factor_gt           0.0405
_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^)+(0.0365P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0746
_refine_ls_wR_factor_ref         0.0836
_reflns_Friedel_coverage         0.000
_reflns_number_gt                12167
_reflns_number_total             16395
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja6b05221_si_004.cif
_cod_data_source_block           p-1twin4
_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_original_cell_volume        3458.5(4)
_cod_database_code               4125109
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.5295(6) 0.4705(6)
2. 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
3. Uiso/Uaniso restraints and constraints
Uanis(C27) = Uanis(C28) = Uanis(C29)
4. Rigid body (RIGU) restrains
 C4, C24, C23, C3, N1
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5.a Ternary CH refined with riding coordinates:
 C19'(H19'), C31(H31), C34(H34), C16(H16), C19(H19), C34'(H34'), C31'(H31'),
 C16'(H16')
5.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C3'(H3'A,H3'B)
5.c Aromatic/amide H refined with riding coordinates:
 C27(H27), C28(H28), C29(H29), C14(H14), C13(H13), C12(H12), C29'(H29'),
 C28'(H28'), C27'(H27'), C12'(H12'), C13'(H13'), C14'(H14')
5.d Idealised Me refined as rotating group:
 C33(H33A,H33B,H33C), C32(H32A,H32B,H32C), C35(H35A,H35B,H35C), C36(H36A,H36B,
 H36C), C23(H23A,H23B,H23C), C24(H24A,H24B,H24C), C22(H22A,H22B,H22C), C17(H17A,
 H17B,H17C), C18(H18A,H18B,H18C), C21(H21A,H21B,H21C), C20(H20A,H20B,H20C),
 C7(H7A,H7B,H7C), C9(H9A,H9B,H9C), C8(H8A,H8B,H8C), C36'(H36D,H36E,H36F),
 C35'(H35D,H35E,H35F), C33'(H33D,H33E,H33F), C32'(H32D,H32E,H32F), C24'(H24D,
 H24E,H24F), C23'(H23D,H23E,H23F), C8'(H8'A,H8'B,H8'C), C21'(H21D,H21E,H21F),
 C20'(H20D,H20E,H20F), C17'(H17D,H17E,H17F), C18'(H18D,H18E,H18F), C7'(H7'A,
 H7'B,H7'C), C9'(H9'A,H9'B,H9'C), C22'(H22D,H22E,H22F)
;
_shelx_res_checksum              66774
_shelx_hkl_checksum              87664
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'