Synthesis of tetrafluoroethylene- and tetrafluoroethyl-containing azides and their 1,3-dipolar cycloaddition as synthetic application
Voltrová, Svatava; Muselli, Mickaël; Filgas, Josef; Matoušek, Václav; Klepetářová, Blanka; Beier, Petr; Org. Biomol. Chem.  (2017) –; doi:10.1039/C7OB01151B

data_7155642
_publ_section_title
;
 Synthesis of tetrafluoroethylene- and tetrafluoroethyl-containing azides
 and their 1,3-dipolar cycloaddition as synthetic application
;
_journal_name_full               'Org. Biomol. Chem.'
_journal_paper_doi               10.1039/C7OB01151B
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C11 H9 F4 N3'
_chemical_formula_sum            'C11 H9 F4 N3'
_chemical_formula_weight         259.20
_chemical_name_systematic
1-(1,1,2,2-tetrafluoroethyl)-4-p-tolyl-1H-1,2,3-triazole
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      4
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_audit_update_record
;
2017-04-20 deposited with the CCDC.
2017-05-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.522(7)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.1098(10)
_cell_length_b                   5.6455(8)
_cell_length_c                   14.581(2)
_cell_measurement_reflns_used    120
_cell_measurement_temperature    180
_cell_measurement_theta_max      52.5024
_cell_measurement_theta_min      10.5207
_cell_volume                     585.23(14)
_computing_cell_refinement       'CrysAlis, (Oxford Diffraction, 2002)'
_computing_data_collection       'Xcalibur, (Oxford Diffraction, 2002)'
_computing_data_reduction        'CrysAlis, (Oxford Diffraction, 2002)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      180
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'Oxford Diffraction XCALIBUR'
_diffrn_measurement_method       '\f & \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.059
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            7865
_diffrn_reflns_theta_full        70.364
_diffrn_reflns_theta_max         70.364
_diffrn_reflns_theta_min         3.031
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.198
_exptl_absorpt_correction_T_max  0.94
_exptl_absorpt_correction_T_min  0.67
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlis, (Oxford Diffraction, 2002)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.471
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             264
_exptl_crystal_size_max          0.811
_exptl_crystal_size_mid          0.101
_exptl_crystal_size_min          0.052
_refine_diff_density_max         0.56
_refine_diff_density_min         -0.46
_refine_ls_abs_structure_details 'Flack (1983), 924 Friedel-pairs'
_refine_ls_abs_structure_Flack   -0.1(5)
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   1.0405
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         1878
_refine_ls_number_restraints     33
_refine_ls_R_factor_all          0.0887
_refine_ls_R_factor_gt           0.0820
_refine_ls_shift/su_max          0.0014035
_refine_ls_shift/su_mean         0.0001456
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details
;
 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 
 [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] 
 where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ 
 A~i~ are: 
 0.779 0.982 0.460 0.169 0.717E-01 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1027
_refine_ls_wR_factor_gt          0.0921
_refine_ls_wR_factor_ref         0.0921
_reflns_limit_h_max              8
_reflns_limit_h_min              -8
_reflns_limit_k_max              6
_reflns_limit_k_min              -6
_reflns_limit_l_max              17
_reflns_limit_l_min              0
_reflns_number_gt                1878
_reflns_number_total             2147
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   4.17
_oxford_diffrn_Wilson_scale      4.27
_oxford_refine_ls_r_factor_ref   0.0820
_oxford_refine_ls_scale          0.649(4)
_oxford_reflns_number_all        2140
_oxford_reflns_threshold_expression_ref I>2.0\s(I)
_iucr_refine_instructions_details_constraints
;
BLOCK SCALE X'S, U'S 
CONT ENANTIO 
SUMFIX ELEMENT SCALES 
RIDE C   (   8,X'S) H   (  81,X'S) 
RIDE C   (  10,X'S) H   ( 101,X'S) 
RIDE C   (  11,X'S) H   ( 111,X'S) 
RIDE C   (  13,X'S) H   ( 131,X'S) 
RIDE C   (  14,X'S) H   ( 141,X'S) 
RIDE C   (  15,X'S) H   ( 153,X'S) H   ( 152,X'S) H   ( 151,X'S) 
RIDE C   (   5,X'S) H   (  51,X'S) 
END                                                                             
;
_iucr_refine_instructions_details_restraints
;
DISTANCE 1.345000 , 0.020000 = F(1) TO C(2) 
DISTANCE 1.345000 , 0.020000 = C(2) TO F(3) 
DISTANCE 1.345000 , 0.020000 = F(16) TO C(5) 
DISTANCE 1.345000 , 0.020000 = F(17) TO C(5) 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
VIBRATION 0.0, 0.020000 = C(2) TO C(5) 
U(IJ)'S  0.0, 0.010000 = C(2) TO C(5) 
VIBRATION 0.0, 0.020000 = C(2) TO N(4) 
U(IJ)'S  0.0, 0.010000 = C(2) TO N(4) 
VIBRATION 0.0, 0.020000 = F(17) TO C(5) 
U(IJ)'S  0.0, 0.010000 = F(17) TO C(5) 
VIBRATION 0.0, 0.020000 = F(16) TO F(17) 
U(IJ)'S  0.0, 0.010000 = F(16) TO F(17) 
END                                                                             
;
_cod_data_source_file            c7ob01151b2.cif
_cod_data_source_block           1
_cod_original_cell_volume        585.25(14)
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7155642