Catalytic Asymmetric Inverse-Electron Demand 1,3-Dipolar Cycloaddition of Isoquinolinium Methylides with Enecarbamates by a ChiralN,N′-Dioxide/Ag(I) Complex
Xu, Yali; Liao, Yuting; Lin, Lili; Zhou, Yuhang; Li, Jun; Liu, Xiaohua; Feng, Xiaoming; ACS Catalysis 6 (2016) 589–; doi:10.1021/acscatal.5b02178

data_4513747
_publ_section_title
;
 Catalytic Asymmetric Inverse-Electron Demand 1,3-Dipolar Cycloaddition of
 Isoquinolinium Methylides with Enecarbamates by a
 ChiralN,N&#x2032;-Dioxide/Ag(I) Complex
;
_journal_issue                   2
_journal_name_full               'ACS Catalysis'
_journal_page_first              589
_journal_paper_doi               10.1021/acscatal.5b02178
_journal_volume                  6
_journal_year                    2016
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C22 H13 F5 N4 O2'
_chemical_formula_sum            'C22 H13 F5 N4 O2'
_chemical_formula_weight         460.36
_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'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2015-07-13
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Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
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_cell_length_a                   7.91984(13)
_cell_length_b                   7.77745(13)
_cell_length_c                   16.8551(3)
_cell_measurement_reflns_used    4872
_cell_measurement_temperature    293
_cell_measurement_theta_max      72.3860
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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
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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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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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;
  1 omega   20.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
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  2 omega   10.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921   77.0000   90.0000 94

  3 omega   20.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921   57.0000   60.0000 84

  4 omega  -31.00   53.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -57.0000  120.0000 84

  5 omega  -31.00   63.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -77.0000  -30.0000 94

  6 omega   20.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921   57.0000 -150.0000 84

  7 omega    1.00   75.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -99.0000    0.0000 74

  8 omega   23.00   90.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921 -125.0000 -160.0000 67

  9 omega   23.00   90.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921 -125.0000  -60.0000 67

 10 omega   40.00   98.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  -90.0000 58

 11 omega   39.00  109.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  -60.0000 70

 12 omega  100.00  178.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000 -180.0000 78

 13 omega   39.00  109.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000   30.0000 70

 14 omega   91.00  176.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000   30.0000 85

 15 omega   40.00   98.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000   30.0000 58

 16 omega   38.00   91.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -30.0000 53

 17 omega   40.00   98.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -150.0000 58

 18 omega   38.00   91.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  120.0000 53

 19 omega   38.00  116.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000  -90.0000 78

 20 omega   39.00  109.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000   90.0000 70

 21 omega   38.00   91.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -60.0000 53

 22 omega   38.00   91.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   90.0000 53

 23 omega   40.00  135.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000  120.0000 95

 24 omega   39.00  177.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000    0.0000 -180.0000 138

 25 omega  -31.00   53.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -57.0000   30.0000 84

 26 omega  -33.00   55.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -38.0000 -180.0000 88

 27 omega   10.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921   77.0000  150.0000 94

 28 omega   20.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921   57.0000  -60.0000 84

 29 omega   10.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921   76.0000 -150.0000 94

 30 omega   10.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921   77.0000    0.0000 94

 31 omega   10.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921   77.0000  -30.0000 94
;
_diffrn_measurement_device       'four-circle diffractometer'
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_diffrn_orient_matrix_UB_12      0.1011276000
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_diffrn_orient_matrix_UB_33      0.0512310000
_diffrn_radiation_monochromator  graphite
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_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0406
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_exptl_absorpt_coefficient_mu    1.135
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.45851
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
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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.
;
_exptl_crystal_colour            'clear light colourless'
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;
;
_exptl_crystal_F_000             468
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;
 Flack x determined using 1352 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(10)
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_refine_ls_number_parameters     298
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_refine_ls_restrained_S_all      1.042
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_refine_ls_structure_factor_coef Fsqd
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'w=1/[\s^2^(Fo^2^)+(0.1078P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
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_cod_depositor_comments          'Adding full bibliography for 4513747.cif.'
_cod_database_code               4513747
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_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Ternary CH refined with riding coordinates:
 C00F(H00F), C00G(H00G)
2.b Secondary CH2 refined with riding coordinates:
 C00V(H00A,H00B), C00X(H00C,H00D)
2.c Aromatic/amide H refined with riding coordinates:
 N003(H003), C00L(H00L), C00N(H00N), C00P(H00P), C00S(H00S), C00T(H00T),
 C00U(H00U)
;
_shelx_res_checksum              24880
_shelx_hkl_checksum              94669
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_olex2_date_sample_data_collection 2015-07-10
_olex2_submission_special_instructions 'No special instructions were received'