Singlet carbenes as mimics for transition metals: synthesis of an air stable organic mixed valence compound [M2(C2)+˙; M = cyclic(alkyl)(amino)carbene]
Jin, Liqun; Melaimi, Mohand; Liu, Liu; Bertrand, Guy; Org. Chem. Front. 1 (2014) 351–; doi:10.1039/C4QO00072B

data_1552986
_publ_section_title
;
 Singlet carbenes as mimics for transition metals: synthesis of an air
 stable organic mixed valence compound [M2(C2)+&#x02D9;; M =
 cyclic(alkyl)(amino)carbene]
;
_journal_issue                   4
_journal_name_full               'Org. Chem. Front.'
_journal_page_first              351
_journal_paper_doi               10.1039/C4QO00072B
_journal_volume                  1
_journal_year                    2014
_chemical_formula_moiety         'C46 H70 N2, 2(Br3)'
_chemical_formula_sum            'C46 H70 Br6 N2'
_chemical_formula_weight         1130.50
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2014-03-12
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2014.02.28 svn.r2899 for OlexSys, GUI svn.r4781)
;
_cell_angle_alpha                90
_cell_angle_beta                 104.823(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.2658(9)
_cell_length_b                   19.7423(12)
_cell_length_c                   17.2861(13)
_cell_measurement_reflns_used    7447
_cell_measurement_temperature    100
_cell_measurement_theta_max      29.997
_cell_measurement_theta_min      2.377
_cell_volume                     4706.4(5)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'APEX2 v2013.6-2 (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.27A (Bruker, 2012)'
_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
_diffrn_detector                 'Bruker APEX-II CCD'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD Area Detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.907
_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_R_equivalents  0.0293
_diffrn_reflns_av_unetI/netI     0.0304
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.907
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            22939
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.907
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         30.513
_diffrn_reflns_theta_min         2.396
_diffrn_source                   'Micro Focus Rotating Anode'
_diffrn_source_type              'Bruker TXS'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    5.151
_exptl_absorpt_correction_T_max  0.0998
_exptl_absorpt_correction_T_min  0.0604
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0691 before and 0.0378 after correction.
The Ratio of minimum to maximum transmission is 0.6052.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            Yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.595
_exptl_crystal_description       Plate
_exptl_crystal_F_000             2280
_exptl_crystal_size_max          0.121
_exptl_crystal_size_mid          0.109
_exptl_crystal_size_min          0.067
_refine_diff_density_max         0.531
_refine_diff_density_min         -0.368
_refine_diff_density_rms         0.074
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         6532
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0425
_refine_ls_R_factor_gt           0.0263
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0174P)^2^+5.4803P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0520
_refine_ls_wR_factor_ref         0.0565
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5045
_reflns_number_total             6532
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c4qo00072b5.cif
_cod_data_source_block           gb_jlq3
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_diffrn_radiation_probe' value 'X-ray' was changed to
'x-ray' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/RSC/depositions/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

data item '_exptl_crystal_colour_primary' value 'Yellow' was changed
to 'yellow' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/RSC/depositions/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_database_code               1552986
_shelxl_version_number           2013-4
_shelx_estimated_absorpt_t_max   0.724
_shelx_estimated_absorpt_t_min   0.575
_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:
 C18(H18), C21(H21)
2.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C6(H6A,H6B), C8(H8A,H8B)
2.c Aromatic/amide H refined with riding coordinates:
 C14(H14), C15(H15), C16(H16)
2.d Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C9(H9A,H9B,H9C), C10(H10A,H10B,H10C), C11(H11A,H11B,H11C),
 C19(H19A,H19B,H19C), C20(H20A,H20B,H20C), C22(H22A,H22B,H22C), C23(H23A,H23B,
 H23C)
;
_shelx_res_checksum              50815