cis-Specific cyanofluorination of vinyl azides enabled by electron-donor-acceptor complexes: synthesis of α-azido-β-fluoronitriles
Wu, Shu-Wei; Liu, Jia-Li; Liu, Feng; Chem. Commun.  (2017) –; doi:10.1039/C7CC07165E

data_7120833
_publ_section_title
;
 cis-Specific cyanofluorination of vinyl azides enabled by
 electron-donor-acceptor complexes: synthesis of
 \a-azido-\b-fluoronitriles
;
_journal_name_full               'Chem. Commun.'
_journal_paper_doi               10.1039/C7CC07165E
_journal_year                    2017
_chemical_formula_moiety         'C20 H17 F N4 O, C H2 Cl2'
_chemical_formula_sum            'C21 H19 Cl2 F N4 O'
_chemical_formula_weight         433.30
_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'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2017-03-28
_audit_creation_method
;
Olex2 1.2
(compiled 2017.02.23 svn.r3390 for OlexSys, GUI svn.r5320)
;
_audit_update_record
;
2017-06-17 deposited with the CCDC.
2017-10-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 108.96(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.168(5)
_cell_length_b                   26.759(9)
_cell_length_c                   9.365(3)
_cell_measurement_reflns_used    939
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      20.6630
_cell_measurement_theta_min      4.5290
_cell_volume                     2172.8(17)
_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
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4471
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details
;
  1 omega   38.00   63.80   0.3000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       10.8090  178.0000   60.0000 86

  2 omega  -52.00   42.20   0.3000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       10.8090  -77.0000   90.0000 314

  3 omega  -11.00   14.20   0.3000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.7465  -99.0000   90.0000 84

  4 omega  -69.00   13.50   0.3000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.7465  -57.0000 -180.0000 275
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0530256000
_diffrn_orient_matrix_UB_12      0.0127759000
_diffrn_orient_matrix_UB_13      -0.0279086000
_diffrn_orient_matrix_UB_21      0.0207891000
_diffrn_orient_matrix_UB_22      -0.0230032000
_diffrn_orient_matrix_UB_23      -0.0256948000
_diffrn_orient_matrix_UB_31      -0.0585786000
_diffrn_orient_matrix_UB_32      0.0033147000
_diffrn_orient_matrix_UB_33      -0.0705643000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1026
_diffrn_reflns_av_unetI/netI     0.1323
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            12518
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.371
_diffrn_reflns_theta_min         3.101
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.326
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.00445
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
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.
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.325
_exptl_crystal_description       block
_exptl_crystal_F_000             896
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.248
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       0.007(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   0.970
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     283
_refine_ls_number_reflns         4444
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.970
_refine_ls_R_factor_all          0.2290
_refine_ls_R_factor_gt           0.0823
_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^)+(0.1000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1930
_refine_ls_wR_factor_ref         0.2800
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1535
_reflns_number_total             4444
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7cc07165e2.cif
_cod_data_source_block           g170327c
_cod_original_cell_volume        2172.7(17)
_cod_database_code               7120833
_shelx_shelxl_version_number     2014/7
_reflns_odcompleteness_completeness 99.65
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Sof(H21D)=Sof(H21C)=Sof(Cl1A)=Sof(Cl2A)=1-FVAR(1)
 Sof(Cl1)=Sof(Cl2)=Sof(H21B)=Sof(H21A)=FVAR(1)
3.a Ternary CH refined with riding coordinates:
 C1(H1)
3.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C21(H21B,H21A), C21(H21D,H21C)
3.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C7(H7), C8(H8), C12(H12), C15(H15), C16(H16), C18(H18),
 C19(H19)
3.d Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C)
;
_olex2_submission_special_instructions 'No special instructions were received'