Defluorinative [4 + 1] annulation of perfluoroalkyl N-mesylhydrazones with primary amines provides 5-fluoroalkyl 1,2,3-triazoles
Ning, Yongquan; Wang, Hongwei; Sivaguru, Paramasivam; Li, Shuang; Zanoni, Giuseppe; Nolan, Steven P.; Bi, Xihe; Green Chemistry 23 (2021) 7976–7981; doi:10.1039/D1GC02749B

data_7243613
_publ_section_title
;
 Defluorinative [4 + 1] annulation of perfluoroalkyl N-mesylhydrazones
 with primary amines provides 5-fluoroalkyl 1,2,3-triazoles
;
_journal_issue                   20
_journal_name_full               'Green Chemistry'
_journal_page_first              7976
_journal_page_last               7981
_journal_paper_doi               10.1039/D1GC02749B
_journal_volume                  23
_journal_year                    2021
_chemical_formula_moiety         'C19 H17 F8 N5 O3'
_chemical_formula_sum            'C19 H17 F8 N5 O3'
_chemical_formula_weight         515.38
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-10-03
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-01-25 deposited with the CCDC.	2021-09-23 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.968(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.1446(13)
_cell_length_b                   6.5924(9)
_cell_length_c                   29.135(4)
_cell_measurement_reflns_used    1152
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      23.6400
_cell_measurement_theta_min      3.8000
_cell_volume                     2135.4(5)
_computing_cell_refinement       'CrysAlisPro 1.171.39.38a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.38a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.38a (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.2375
_diffrn_detector_type            Ruby
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.859
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -73.00  14.00   1.00   20.00    --   -9.76 -77.00 120.00   87
  2  \w    -81.00  -8.00   1.00   20.00    --   -9.76 -57.00-150.00   73
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Ruby, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0612332000
_diffrn_orient_matrix_UB_12      -0.0183541000
_diffrn_orient_matrix_UB_13      -0.0036953000
_diffrn_orient_matrix_UB_21      0.0144600000
_diffrn_orient_matrix_UB_22      0.0037528000
_diffrn_orient_matrix_UB_23      0.0240994000
_diffrn_orient_matrix_UB_31      -0.0101730000
_diffrn_orient_matrix_UB_32      -0.1059630000
_diffrn_orient_matrix_UB_33      0.0014770000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0230
_diffrn_reflns_av_unetI/netI     0.0502
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.859
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            4874
_diffrn_reflns_point_group_measured_fraction_full 0.735
_diffrn_reflns_point_group_measured_fraction_max 0.599
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.212
_diffrn_reflns_theta_min         3.593
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.157
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90668
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.38a (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.603
_exptl_crystal_description       block
_exptl_crystal_F_000             1048
_refine_diff_density_max         0.304
_refine_diff_density_min         -0.211
_refine_diff_density_rms         0.053
_refine_ls_abs_structure_details
;
 Flack x determined using 524 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.0(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     316
_refine_ls_number_reflns         3460
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.015
_refine_ls_R_factor_all          0.0970
_refine_ls_R_factor_gt           0.0646
_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^)+(0.0864P)^2^+1.8913P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1551
_refine_ls_wR_factor_ref         0.1818
_reflns_Friedel_coverage         0.290
_reflns_Friedel_fraction_full    0.426
_reflns_Friedel_fraction_max     0.294
_reflns_number_gt                2342
_reflns_number_total             3460
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1gc02749b2.cif
_cod_data_source_block           200828-bxh01-pwy
_cod_depositor_comments          'Adding full bibliography for 7243613.cif.'
_cod_database_code               7243613
_shelx_shelxl_version_number     2018/3
_reflns_odcompleteness_completeness 99.07
_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
2.a Ternary CH refined with riding coordinates:
 C00I(H00I)
2.b Secondary CH2 refined with riding coordinates:
 C00J(H00A,H00C), C00K(H00D,H00G), C00L(H00H,H00J), C00M(H00K,H00L), C00Q(H00M,
 H00N), C00R(H00O,H00P)
2.c Aromatic/amide H refined with riding coordinates:
 C00B(H00B), C00E(H00E), C00F(H00F), C00X(H00X)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.410
_oxdiff_exptl_absorpt_empirical_full_min 0.784