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_1507592
_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 rmad
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C38 H48 Cl2 N6 Rh2'
_chemical_formula_sum            'C38 H48 Cl2 N6 Rh2'
_chemical_formula_weight         865.54
_chemical_name_systematic
;
 ?
;
_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             2011-10-19T22:13:59-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.24040(10)
_cell_length_b                   16.95630(10)
_cell_length_c                   17.67910(10)
_cell_measurement_reflns_used    20556
_cell_measurement_temperature    100(1)
_cell_measurement_theta_max      76.2297
_cell_measurement_theta_min      2.4972
_cell_measurement_wavelength     1.54184
_cell_volume                     3669.33(4)
_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 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_details
;
  1 omega -113.00  -21.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -40.7631  -38.0000   60.0000 92

  2 omega  -25.00   58.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       40.7631  -38.0000 -180.0000 83

  3 omega   60.00   98.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       40.7631 -125.0000   60.0000 38

  4 omega   39.00   75.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000    0.0000 36

  5 omega   49.00  141.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -77.0000   60.0000 92

  6 omega   92.00  158.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000    0.0000 66

  7 omega   40.00   72.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000 -120.0000 32

  8 omega   44.00   70.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000   90.0000 26

  9 omega   58.00  118.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -120.0000   73.0000 60

 10 omega  108.00  149.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000  -90.0000 41

 11 omega   50.00   76.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000  -60.0000 26

 12 omega  117.00  158.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000 -120.0000 41

 13 omega   79.00  115.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000 -120.0000 36

 14 omega   14.00  117.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       40.7631   38.0000    0.0000 103

 15 omega   11.00   98.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       40.7631 -125.0000 -150.0000 87

 16 omega   45.00   73.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000   60.0000 28

 17 omega   67.00  147.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -77.0000  -90.0000 80

 18 omega   97.00  152.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   15.0000 -120.0000 55

 19 omega   60.00   93.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   15.0000 -120.0000 33

 20 omega   38.00   73.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000  -90.0000 35

 21 omega  107.00  154.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   15.0000  150.0000 47

 22 omega   40.00  118.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -77.0000 -180.0000 78

 23 omega   60.00   88.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   15.0000  150.0000 28

;
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'Agilent SuperNova'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0199211
_diffrn_orient_matrix_UB_12      0.0386395
_diffrn_orient_matrix_UB_13      0.0776491
_diffrn_orient_matrix_UB_21      0.0074012
_diffrn_orient_matrix_UB_22      -0.0814751
_diffrn_orient_matrix_UB_23      0.0381729
_diffrn_orient_matrix_UB_31      0.1240689
_diffrn_orient_matrix_UB_32      0.0111042
_diffrn_orient_matrix_UB_33      0.010244
_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  0.0238
_diffrn_reflns_av_unetI/netI     0.021
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            26162
_diffrn_reflns_theta_full        74.98
_diffrn_reflns_theta_max         74.98
_diffrn_reflns_theta_min         3.61
_diffrn_source_current           0.8
_diffrn_source_power             0.04
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    8.892
_exptl_absorpt_correction_T_max  0.507
_exptl_absorpt_correction_T_min  0.272
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
        (compiled May 16 2011,17:55:39)
Numerical absorption correction based on gaussian integration over
                        a multifaceted crystal model
;
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.567
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'Cut fragment'
_exptl_crystal_F_000             1768
_exptl_crystal_size_max          0.224
_exptl_crystal_size_mid          0.178
_exptl_crystal_size_min          0.170
_refine_diff_density_max         0.392
_refine_diff_density_min         -0.378
_refine_diff_density_rms         0.054
_refine_ls_abs_structure_details
;
The Friedel pair coverage of the experiment is almost complete (99%).
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=-0.013(1), 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   -0.012(4)
_refine_ls_extinction_coef       0.000284(19)
_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   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     438
_refine_ls_number_reflns         7495
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0168
_refine_ls_R_factor_gt           0.0167
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0233P)^2^+1.4239P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0421
_refine_ls_wR_factor_ref         0.0422
_reflns_number_gt                7448
_reflns_number_total             7495
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            ol3004657_si_001.cif
_cod_data_source_block           3c
_cod_database_code               1507592