Asymmetric Intramolecular Desymmetrization of meso-α,α'-Diazido Alcohols with Aryldiazoacetates: Assembly of Chiral C3 Fragments with Three Continuous Stereocenters.
Qiao, Jin-Bao; Zhao, Yu-Ming; Gu, Peiming; Organic letters 18 (2016) 1984–1987; doi:10.1021/acs.orglett.6b00570

data_1555521
_publ_section_title
;
 Asymmetric Intramolecular Desymmetrization of meso-\a,\a'-Diazido
 Alcohols with Aryldiazoacetates: Assembly of Chiral C3 Fragments with
 Three Continuous Stereocenters.
;
_journal_issue                   9
_journal_name_full               'Organic letters'
_journal_page_first              1984
_journal_page_last               1987
_journal_paper_doi               10.1021/acs.orglett.6b00570
_journal_volume                  18
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C23 H16 F2 N4 O2'
_chemical_formula_sum            'C23 H16 F2 N4 O2'
_chemical_formula_weight         418.40
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2015-11-10
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Olex2 1.2
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_cell_length_c                   9.3787(7)
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_cell_measurement_theta_min      5.9220
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_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
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_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
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_diffrn_measured_fraction_theta_full 0.971
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_details
;
  1 omega  112.00  170.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000   30.0000 58

  2 omega  141.00  169.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   63.0000  150.0000 28

  3 omega   87.00  125.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   63.0000  150.0000 38

  4 omega   88.00  130.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000   90.0000 42

  5 omega   41.00  114.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   57.0000   90.0000 73

  6 omega   38.00   97.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -50.0000  150.0000 59

  7 omega   43.00   68.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000   30.0000 25

  8 omega   87.00  113.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000   30.0000 26

  9 omega   79.00  127.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -63.0000    0.0000 48

 10 omega   49.00   96.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000  -60.0000 47

 11 omega   60.00   86.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000 -150.0000 26

 12 omega   24.00  110.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000 -125.0000 -150.0000 86

 13 omega   41.00   75.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -63.0000    0.0000 34

 14 omega   38.00   99.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -50.0000   90.0000 61

 15 omega   26.00   52.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   57.0000  -90.0000 26

 16 omega   45.00   98.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   57.0000 -180.0000 53

 17 omega   19.00   73.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -57.0000 -150.0000 54

 18 omega  -13.00   13.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -77.0000  150.0000 26
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
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_diffrn_orient_matrix_UB_11      0.0666813000
_diffrn_orient_matrix_UB_12      -0.0965330000
_diffrn_orient_matrix_UB_13      -0.0061287000
_diffrn_orient_matrix_UB_21      -0.1898788000
_diffrn_orient_matrix_UB_22      -0.0229312000
_diffrn_orient_matrix_UB_23      -0.1299411000
_diffrn_orient_matrix_UB_31      0.0722652000
_diffrn_orient_matrix_UB_32      0.0288517000
_diffrn_orient_matrix_UB_33      -0.1234111000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0179
_diffrn_reflns_av_unetI/netI     0.0305
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       17
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_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            3659
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_diffrn_reflns_theta_max         69.90
_diffrn_reflns_theta_min         5.94
_diffrn_source                   'sealed X-ray tube'
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_exptl_absorpt_coefficient_mu    0.869
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
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_exptl_crystal_colour            'clear dark yellow'
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_exptl_crystal_density_method    'not measured'
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_exptl_crystal_F_000             432
_exptl_crystal_size_max          0.2
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_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.01(16)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
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_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0362
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_refine_ls_structure_factor_coef Fsqd
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'calc w=1/[\s^2^(Fo^2^)+(0.0397P)^2^+0.0537P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
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_cod_database_code               1555521
_reflns_odcompleteness_completeness 99.58
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_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1), C2(H2), C17(H17)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C8(H8), C9(H9), C10(H10), C12(H12), C13(H13), C15(H15),
 C16(H16), C19(H19), C20(H20), C22(H22), C23(H23)
;
_olex2_date_sample_data_collection 2015-11-10
_olex2_submission_special_instructions 'No special instructions were received'