Bicyclic (Alkyl)(amino)carbenes (BICAACs): Stable Carbenes more Ambiphilic than CAACs.
Tomás-Mendivil, Eder; Hansmann, Max M.; Weinstein, Cory M.; Jazzar, Rodolphe; Melaimi, Mohand; Bertrand, Guy; Journal of the American Chemical Society  (2017) –; doi:10.1021/jacs.7b04640

data_4126087
_publ_section_title
;
 Bicyclic (Alkyl)(amino)carbenes (BICAACs): Stable Carbenes more
 Ambiphilic than CAACs.
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_paper_doi               10.1021/jacs.7b04640
_journal_year                    2017
_chemical_formula_moiety         'Br2 Cu, 2(C22 H33 Cu0.5 N)'
_chemical_formula_sum            'C44 H66 Br2 Cu2 N2'
_chemical_formula_weight         909.88
_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
_atom_sites_solution_primary     direct
_audit_creation_date             2017-04-11
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_cell_angle_alpha                102.972(5)
_cell_angle_beta                 92.218(5)
_cell_angle_gamma                112.649(5)
_cell_formula_units_Z            2
_cell_length_a                   10.4452(15)
_cell_length_b                   11.9506(19)
_cell_length_c                   18.948(3)
_cell_measurement_reflns_used    9991
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      25.33
_cell_measurement_theta_min      2.22
_cell_volume                     2106.4(6)
_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  'XL (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 0.999
_diffrn_measured_fraction_theta_max 0.993
_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_radiation_xray_symbol    K-L~3~
_diffrn_reflns_av_R_equivalents  0.0731
_diffrn_reflns_av_unetI/netI     0.0583
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            47761
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.437
_diffrn_reflns_theta_min         1.912
_diffrn_source                   'sealed tube'
_diffrn_source_type              fine-focus
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.938
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6378
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0715 before and 0.0486 after correction. The Ratio of minimum to maximum transmission is 0.8559. The \l/2 correction factor is 0.00150.'
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.435
_exptl_crystal_description       block
_exptl_crystal_F_000             944
_exptl_crystal_recrystallization_method DCM/Et2O
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         1.517
_refine_diff_density_min         -1.075
_refine_diff_density_rms         0.107
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     468
_refine_ls_number_reflns         7741
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0631
_refine_ls_R_factor_gt           0.0443
_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^)+(0.0610P)^2^+3.2595P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1193
_refine_ls_wR_factor_ref         0.1243
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5778
_reflns_number_total             7741
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja7b04640_si_002.cif
_cod_data_source_block           6a
_cod_depositor_comments
;
The following automatic conversions were performed:

'_diffrn_radiation_probe' value 'X-ray' changed to 'x-ray' according
to
/home/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 4973 2017-02-22 13:04:09Z antanas 
;
_cod_database_code               4126087
_shelx_shelxl_version_number     2014/7
_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:
 C19(H19), C3A(H3A), C19A(H19A), C16A(H16A), C16(H16), C3(H3)
2.b Secondary CH2 refined with riding coordinates:
 C6A(H6AA,H6AB), C4A(H4AA,H4AB), C4(H4A,H4B), C7A(H7AA,H7AB), C6(H6A,H6B),
 C7(H7A,H7B)
2.c Aromatic/amide H refined with riding coordinates:
 C14(H14), C14A(H14A), C12(H12), C12A(H12A), C13(H13), C13A(H13A)
2.d Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C21(H21A,H21B,H21C), C22(H22A,H22B,H22C), C20A(H20D,H20E,
 H20F), C22A(H22D,H22E,H22F), C8A(H8AA,H8AB,H8AC), C17(H17A,H17B,H17C),
 C20(H20A,H20B,H20C), C17A(H17D,H17E,H17F), C21A(H21D,H21E,H21F), C18(H18A,H18B,
 H18C), C18A(H18D,H18E,H18F), C9A(H9AA,H9AB,H9AC), C9(H9A,H9B,H9C)
;
_shelx_res_checksum              61869
_shelx_hkl_checksum              39096
_olex2_exptl_crystal_mounting_method fomblin
_olex2_submission_special_instructions 'No special instructions were received'