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_7155645
_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_formula_moiety         'C17 H13 F4 N3 O2'
_chemical_formula_sum            'C17 H13 F4 N3 O2'
_chemical_formula_weight         367.30
_chemical_name_systematic
4-phenyl-1-(1,1,2,2-tetrafluoro-2-(4-methoxyphenoxy)ethyl)-1H-1,2,3-triazole
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 95.884(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   18.5871(12)
_cell_length_b                   5.6567(4)
_cell_length_c                   15.3181(11)
_cell_measurement_reflns_used    2987
_cell_measurement_temperature    180
_cell_measurement_theta_max      75.7730
_cell_measurement_theta_min      5.7750
_cell_volume                     1602.08(19)
_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 0.987
_diffrn_measured_fraction_theta_max 0.946
_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     1.54180
_diffrn_reflns_av_R_equivalents  0.043
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            6578
_diffrn_reflns_theta_full        68.976
_diffrn_reflns_theta_max         75.910
_diffrn_reflns_theta_min         4.783
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.162
_exptl_absorpt_correction_T_max  0.84
_exptl_absorpt_correction_T_min  0.71
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlis, (Oxford Diffraction, 2002)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.523
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.620
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.150
_refine_diff_density_max         0.31
_refine_diff_density_min         -0.31
_refine_ls_extinction_coef       39(5)
_refine_ls_extinction_method     'Larson (1970), Equation 22'
_refine_ls_goodness_of_fit_ref   1.1449
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         2402
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0636
_refine_ls_R_factor_gt           0.0477
_refine_ls_shift/su_max          0.0004556
_refine_ls_shift/su_mean         0.0000539
_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: 
 7.51 -2.16 6.14 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0543
_refine_ls_wR_factor_gt          0.0476
_refine_ls_wR_factor_ref         0.0476
_reflns_limit_h_max              23
_reflns_limit_h_min              -23
_reflns_limit_k_max              6
_reflns_limit_k_min              0
_reflns_limit_l_max              19
_reflns_limit_l_min              0
_reflns_number_gt                2402
_reflns_number_total             3165
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   3.31
_oxford_diffrn_Wilson_scale      0.08
_oxford_refine_ls_r_factor_ref   0.0477
_oxford_refine_ls_scale          3.643(9)
_oxford_reflns_number_all        3165
_oxford_reflns_threshold_expression_ref I>2.0\s(I)
_cod_data_source_file            c7ob01151b2.cif
_cod_data_source_block           1
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7155645
_iucr_refine_instruction_details_constraints
;
BLOCK SCALE X'S, U'S 
CONT EXTPARAM 
RIDE C   (   6,X'S) H   (  61,X'S) 
RIDE C   (   7,X'S) H   (  71,X'S) 
RIDE C   (  10,X'S) H   ( 101,X'S) H   ( 102,X'S) H   ( 103,X'S) 
RIDE C   (  11,X'S) H   ( 111,X'S) 
RIDE C   (  19,X'S) H   ( 191,X'S) 
RIDE C   (  21,X'S) H   ( 211,X'S) 
RIDE C   (  22,X'S) H   ( 221,X'S) 
RIDE C   (  23,X'S) H   ( 231,X'S) 
RIDE C   (  24,X'S) H   ( 241,X'S) 
RIDE C   (  25,X'S) H   ( 251,X'S) 
RIDE C   (   1,X'S) H   (  11,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                                                                             
;