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_1552985
_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, 0.5(Br2 H6 O2)'
_chemical_formula_sum            'C46 H73 Br N2 O'
_chemical_formula_weight         749.97
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_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                 101.929(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.3761(9)
_cell_length_b                   13.3939(13)
_cell_length_c                   16.9447(17)
_cell_measurement_reflns_used    2976
_cell_measurement_temperature    100
_cell_measurement_theta_max      26.337
_cell_measurement_theta_min      2.761
_cell_volume                     2082.0(4)
_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 0.997
_diffrn_measured_fraction_theta_max 0.991
_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  0.0879
_diffrn_reflns_av_unetI/netI     0.0760
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            20297
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         26.510
_diffrn_reflns_theta_min         1.955
_diffrn_source                   'Micro Focus Rotating Anode'
_diffrn_source_type              'Bruker TXS'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.023
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6414
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.1617 before and 0.0534 after correction.
The Ratio of minimum to maximum transmission is 0.8605.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            Red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.196
_exptl_crystal_description       Plate
_exptl_crystal_F_000             812
_exptl_crystal_size_max          0.117
_exptl_crystal_size_mid          0.103
_exptl_crystal_size_min          0.053
_refine_diff_density_max         0.323
_refine_diff_density_min         -0.544
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     252
_refine_ls_number_reflns         4277
_refine_ls_number_restraints     5
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0886
_refine_ls_R_factor_gt           0.0546
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0480P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1034
_refine_ls_wR_factor_ref         0.1123
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2891
_reflns_number_total             4277
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c4qo00072b5.cif
_cod_data_source_block           gb_jlq2_0m
_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 'Red' was changed to
'red' 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               1552985
_shelxl_version_number           2013-4
_shelx_estimated_absorpt_t_max   0.948
_shelx_estimated_absorpt_t_min   0.890
_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, All O(H,H,H) groups
2. Restrained distances
 O1S-H1S = O1S-H1SA = O1S-H1SB
 0.9 with sigma of 0.02
 H1SA-H1S
 1.4 with sigma of 0.02
 H1S-H1SB
 1.4 with sigma of 0.02
3. Others
 Fixed Sof: Br1(0.5) O1S(0.5) H1SB(0.5) H1S(0.5) H1SA(0.5)
4.a Ternary CH refined with riding coordinates:
 C18(H18), C21(H21)
4.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C8(H8A,H8B), C6(H6A,H6B)
4.c Aromatic/amide H refined with riding coordinates:
 C14(H14), C15(H15), C16(H16)
4.d Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C23(H23A,H23B,H23C), C20(H20A,H20B,H20C), C11(H11A,H11B,
 H11C), C9(H9A,H9B,H9C), C10(H10A,H10B,H10C), C22(H22A,H22B,H22C), C7(H7A,H7B,
 H7C)
;
_shelx_res_checksum              27314