Introducing Axial Chirality into Mesoionic 4,4'-Bis(1,2,3-triazole) Dicarbenes.
Aizpurua, Jesus M.; Sagartzazu-Aizpurua, Maialen; Monasterio, Zaira; Azcune, Itxaso; Mendicute, Claudio; Miranda, Jose I.; García-Lecina, Eva; Altube, Ainhoa; Fratila, Raluca M.; Organic letters 14 (2012) 1866–1868; doi:10.1021/ol3004657

data_1507591
_publ_section_title
;
 Introducing Axial Chirality into Mesoionic 4,4'-Bis(1,2,3-triazole)
 Dicarbenes.
;
_journal_issue                   7
_journal_name_full               'Organic letters'
_journal_page_first              1866
_journal_page_last               1868
_journal_paper_doi               10.1021/ol3004657
_journal_volume                  14
_journal_year                    2012
_chemical_absolute_configuration ad
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C37 H46 Cl2 N6 Rh2'
_chemical_formula_sum            'C37 H46 Cl2 N6 Rh2'
_chemical_formula_weight         851.52
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      19
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2011-10-28T17:06:03-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   11.58880(10)
_cell_length_b                   20.8645(2)
_cell_length_c                   29.5473(3)
_cell_measurement_reflns_used    21003
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      76.2591
_cell_measurement_theta_min      2.5904
_cell_measurement_wavelength     1.54184
_cell_volume                     7144.38(12)
_computing_cell_refinement       'CrysAlis Pro (Oxford Diffraction Ltd., 2011)'
_computing_data_collection       'CrysAlis Pro (Oxford Diffraction Ltd., 2011)'
_computing_data_reduction        'CrysAlis Pro (Oxford Diffraction Ltd., 2011)'
_computing_molecular_graphics    'Diamond v.3.2f (Crystal Impact GbR, 2008)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR92 (Altomare et al, 1993)'
_diffrn_ambient_temperature      100(1)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4023
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
  1 omega -110.00  -16.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -40.6693  -38.0000  120.0000 94

  2 omega   22.00   86.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       40.6693 -108.0000  110.0000 64

  3 omega    3.00   65.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       40.6693  -38.0000  -60.0000 62

  4 omega   42.00  116.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -123.0000   70.0000 74

  5 omega  120.00  158.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000 -180.0000 38

  6 omega   39.00   77.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000  -60.0000 38

  7 omega   48.00   73.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000  120.0000 25

  8 omega   42.00   71.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000 -180.0000 29

  9 omega   42.00   68.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000  -90.0000 26

 10 omega   47.00   75.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000    0.0000 28

 11 omega   35.00  114.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -108.0000  110.0000 79

 12 omega   36.00  149.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -15.0000 -180.0000 113

 13 omega -117.00  -14.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -40.6693  -38.0000 -120.0000 103

 14 omega -119.00   -7.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -40.6693  -77.0000   30.0000 112

 15 omega  -35.00   67.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       40.6693  -38.0000 -150.0000 102

 16 omega   85.00  115.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000 -120.0000 30

 17 omega   79.00  158.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000    0.0000 79

 18 omega   85.00  158.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000  -60.0000 73

;
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'Agilent SuperNova'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.1205573
_diffrn_orient_matrix_UB_12      0.0184129
_diffrn_orient_matrix_UB_13      0.017758
_diffrn_orient_matrix_UB_21      0.0466797
_diffrn_orient_matrix_UB_22      -0.0001011
_diffrn_orient_matrix_UB_23      -0.0487908
_diffrn_orient_matrix_UB_31      -0.0312118
_diffrn_orient_matrix_UB_32      0.0714887
_diffrn_orient_matrix_UB_33      -0.0046131
_diffrn_radiation_monochromator  'Multilayer optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'Nova (Cu) X-ray micro-source'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.043
_diffrn_reflns_av_unetI/netI     0.0419
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            45967
_diffrn_reflns_theta_full        74.99
_diffrn_reflns_theta_max         74.99
_diffrn_reflns_theta_min         2.59
_diffrn_source_current           0.8
_diffrn_source_power             0.04
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    9.123
_exptl_absorpt_correction_T_max  0.525
_exptl_absorpt_correction_T_min  0.295
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
        (compiled Jan 20 2011,15:58:25)
Numerical absorption correction based on gaussian integration over
                        a multifaceted crystal model
;
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.583
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'Cut fragment'
_exptl_crystal_F_000             3472
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.15
_refine_diff_density_max         1.028
_refine_diff_density_min         -1.089
_refine_diff_density_rms         0.236
_refine_ls_abs_structure_details
;
The Friedel pair coverage of the experiment is almost complete (98%).
Analysis of the absolute structure using likelihood methods
(Hooft, Straver & Spek, 2008) was performed using PLATON (Spek, 2011).
 The results indicated that the absolute structure had been correctly
 assigned. The method calculated that the probability that the structure 
is inverted is smaller than 10-99. The absolute structure parameter y 
(Hooft, Straver & Spek, 2008) was calculated using PLATON (Spek,
2010). The resulting value was y=-0.028(5), which together with Flack parameter 
value, indicate that the absolute structure has surely been determined 
correctly.

Flack, H. D. (1983), Acta Cryst. A39, 876-881
Flack & G. Bernardinelli, Acta Cryst. 1999, A55, 908-915; 
H. D. Flack & G. Bernardinelli, J. Appl. Cryst. 2000, 33, 1143-1148.

R. W. W. Hooft, L. H. Straver & A. L. Spek, J. Appl. Cryst. 2008, 41, 96-103
A. L. Spek (2010) PLATON, Utrecht, The Netherlands; 
A. L. Spek, J. Appl. Cryst. 2003, 36, 7-13
A. L. Thompson & D. J. Watkin, Tetrahedron: Asymmetry 2009, 20, 712--717

;
_refine_ls_abs_structure_Flack   -0.035(7)
_refine_ls_extinction_coef       0.000031(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     876
_refine_ls_number_reflns         14537
_refine_ls_number_restraints     24
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0425
_refine_ls_R_factor_gt           0.0379
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0179P)^2^+17.3070P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0797
_refine_ls_wR_factor_ref         0.0828
_reflns_number_gt                13502
_reflns_number_total             14537
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            ol3004657_si_001.cif
_cod_data_source_block           3b
_cod_database_code               1507591