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_7155646
_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         'C17 H13 F4 N3 S1'
_chemical_formula_sum            'C17 H13 F4 N3 S'
_chemical_formula_weight         367.37
_chemical_name_systematic
1-(1,1,2,2-tetrafluoro-2-(phenylthio)ethyl)-4-(p-tolyl)-1H-1,2,3-triazole
_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
_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
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.3006(6)
_cell_length_b                   8.6660(10)
_cell_length_c                   35.753(4)
_cell_measurement_reflns_used    166
_cell_measurement_temperature    180
_cell_measurement_theta_max      54.9020
_cell_measurement_theta_min      10.4851
_cell_volume                     1642.3(3)
_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 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.057
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       42
_diffrn_reflns_limit_l_min       -43
_diffrn_reflns_number            19043
_diffrn_reflns_theta_full        68.227
_diffrn_reflns_theta_max         68.227
_diffrn_reflns_theta_min         2.472
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.196
_exptl_absorpt_correction_T_max  0.88
_exptl_absorpt_correction_T_min  0.69
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlis, (Oxford Diffraction, 2002)'
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_diffrn    1.486
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.626
_exptl_crystal_size_mid          0.356
_exptl_crystal_size_min          0.058
_refine_diff_density_max         0.40
_refine_diff_density_min         -0.36
_refine_ls_abs_structure_details 'Flack (1983), 1208 Friedel-pairs'
_refine_ls_abs_structure_Flack   0.14(3)
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   0.9687
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         2465
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0773
_refine_ls_R_factor_gt           0.0621
_refine_ls_shift/su_max          0.0010944
_refine_ls_shift/su_mean         0.0000284
_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: 
 0.533 0.427 0.300 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0679
_refine_ls_wR_factor_gt          0.0587
_refine_ls_wR_factor_ref         0.0587
_reflns_limit_h_max              6
_reflns_limit_h_min              -6
_reflns_limit_k_max              10
_reflns_limit_k_min              0
_reflns_limit_l_max              42
_reflns_limit_l_min              0
_reflns_number_gt                2465
_reflns_number_total             3016
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   3.42
_oxford_diffrn_Wilson_scale      19.19
_oxford_refine_ls_r_factor_ref   0.0621
_oxford_refine_ls_scale          0.2382(7)
_oxford_reflns_number_all        3015
_oxford_reflns_threshold_expression_ref I>2.0\s(I)
_cod_data_source_file            c7ob01151b2.cif
_cod_data_source_block           1
_cod_original_formula_sum        'C17 H13 F4 N3 S1'
_cod_database_code               7155646
_iucr_refine_instruction_details_constraints
;
BLOCK SCALE X'S, U'S 
CONT ENANTIO 
RIDE C   (   3,X'S) H   (  31,X'S) 
RIDE C   (   4,X'S) H   (  41,X'S) 
RIDE C   (   5,X'S) H   (  51,X'S) 
RIDE C   (   6,X'S) H   (  61,X'S) 
RIDE C   (   7,X'S) H   (  71,X'S) 
RIDE C   (  18,X'S) H   ( 181,X'S) 
RIDE C   (  20,X'S) H   ( 201,X'S) 
RIDE C   (  21,X'S) H   ( 211,X'S) 
RIDE C   (  23,X'S) H   ( 231,X'S) H   ( 232,X'S) H   ( 233,X'S) 
RIDE C   (  24,X'S) H   ( 241,X'S) 
RIDE C   (  25,X'S) H   ( 251,X'S) 
END                                                                             
;
_iucr_refine_instruction_details_restraints
;
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;