Transition metal-free controlled synthesis of bis[(trifluoromethyl)sulfonyl]ethyl-decorated heterocycles
Almendros, Pedro; Yanai, Hikaru; Hoshikawa, Shoki; Aragoncillo, Cristina; Lázaro-Milla, Carlos; Toledano-Pinedo, Mireia; Matsumoto, Takashi; Alcaide, Benito; Organic Chemistry Frontiers 5 (2018) 3163–; doi:10.1039/C8QO00955D

data_1554479
_publ_section_title
;
 Transition metal-free controlled synthesis of
 bis[(trifluoromethyl)sulfonyl]ethyl-decorated heterocycles
;
_journal_issue                   21
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              3163
_journal_paper_doi               10.1039/C8QO00955D
_journal_volume                  5
_journal_year                    2018
_chemical_formula_moiety         'C9 H10 F6 N2 O5 S2'
_chemical_formula_sum            'C9 H10 F6 N2 O5 S2'
_chemical_formula_weight         404.31
_chemical_melting_point          441
_chemical_name_systematic
;
2-(5-hydroxy-1,3-dimethyl-1H-pyrazol-2-ium-4-yl)-
1,1-bis((trifluoromethyl)sulfonyl)ethan-1-ide 
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2018-02-15
_audit_creation_method           SHELXL-2014
_audit_update_record
;
2018-03-24 deposited with the CCDC.
2018-09-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            16
_cell_length_a                   17.2641(10)
_cell_length_b                   14.8304(8)
_cell_length_c                   23.9088(14)
_cell_measurement_reflns_used    7817
_cell_measurement_temperature    90
_cell_measurement_theta_max      27.18
_cell_measurement_theta_min      2.36
_cell_volume                     6121.5(6)
_computing_cell_refinement       'APEX2 V2014.11-0 (Bruker AXS Inc.,2014)'
_computing_data_collection       'APEX2 V2014.11-0 (Bruker AXS Inc.,2014)'
_computing_data_reduction        'SAINT V8.34a (Bruker AXS Inc., 2013)'
_computing_molecular_graphics    'Platon (A.L.Spek, 2003)'
_computing_publication_material
;
pubCIF (Westrip, 2010) and enCIFer (Allen et al. 2004)
;
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution
'SHELXTL XT Intrinsic Phasing (Sheldrick, 2013)'
_diffrn_ambient_temperature      90
_diffrn_detector_area_resol_mean 8.333
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker D8 goniometer'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_monochromator  'Bruker Helios multilayered confocal mirror'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0343
_diffrn_reflns_av_unetI/netI     0.0252
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            28505
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.026
_diffrn_reflns_theta_min         1.703
_diffrn_source                   'rotating-anode X-ray tube'
_diffrn_source_type              'Bruker TXS fine-focus Turbo X-ray Source'
_exptl_absorpt_coefficient_mu    0.440
_exptl_absorpt_correction_T_max  0.927
_exptl_absorpt_correction_T_min  0.869
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;
Crystal Faces plugin in Bruker APEX2 software
;
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.755
_exptl_crystal_description       block
_exptl_crystal_F_000             3264
_exptl_crystal_size_max          0.293
_exptl_crystal_size_mid          0.263
_exptl_crystal_size_min          0.174
_refine_diff_density_max         0.498
_refine_diff_density_min         -0.431
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     445
_refine_ls_number_reflns         5403
_refine_ls_number_restraints     576
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0451
_refine_ls_R_factor_gt           0.0373
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0394P)^2^+6.9113P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0889
_refine_ls_wR_factor_ref         0.0929
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4636
_reflns_number_total             5403
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8qo00955d2.cif
_cod_data_source_block           SH-114a
_cod_database_code               1554479
_shelx_estimated_absorpt_t_min   0.882
_shelx_estimated_absorpt_t_max   0.927
_shelx_res_checksum              20243
_shelx_hkl_checksum              25484