NH±F Hydrogen Bonding in a Fluorinated "Proton Sponge" Derivative: Integration of Solution, Solid-State, Gas-Phase, and Computational Studies
Michael T. Scerba; Christopher M. Leavitt; Matthew E. Diener; Andrew F. DeBlase; Timothy L. Guasco; Maxime A. Siegler; Nathaniel Bair; Mark A. Johnson; Thomas Lectka; Journal of Organic Chemistry 76 (2011) 7975–7984; doi:10.1021/jo2015328

data_4026629
_publ_contact_author_address
;Department of Chemistry
New Chemistry Building
Johns Hopkins University
3400 North Charles St.
Baltimore, Maryland 21218
;
_publ_contact_author_email       lectka@jhu.edu
_publ_contact_author_name        'Thomas Lectka'
_publ_contact_author_phone       410.516.6448
_publ_section_title
;
 NH+-F Hydrogen Bonding in a Fluorinated "Proton Sponge" Derivative:
 Integration of Solution, Solid-State, Gas-Phase, and Computational
 Studies
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              7975
_journal_page_last               7984
_journal_paper_doi               10.1021/jo2015328
_journal_volume                  76
_journal_year                    2011
_chemical_formula_moiety         'C12 H13 F N, C F3 O3 S'
_chemical_formula_sum            'C13 H13 F4 N O3 S'
_chemical_formula_weight         339.30
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_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
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 107.618(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.00240(17)
_cell_length_b                   19.7499(3)
_cell_length_c                   10.8637(3)
_cell_measurement_reflns_used    7660
_cell_measurement_temperature    110(2)
_cell_measurement_theta_max      27.61
_cell_measurement_theta_min      1.96
_cell_volume                     1431.94(6)
_computing_cell_refinement
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET)
(compiled Jan  5 2010,16:28:46)
;
_computing_data_collection
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET)
(compiled Jan  5 2010,16:28:46)
;
_computing_data_reduction
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET)
(compiled Jan  5 2010,16:28:46)
;
_computing_molecular_graphics    'SHELXTL v6.10 (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL v6.10 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      110(2)
_diffrn_detector_area_resol_mean 15.9890
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Goniometer KM4/Xcalibur, detector: Sapphire3'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0385
_diffrn_reflns_av_sigmaI/netI    0.0346
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            13961
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         2.06
_exptl_absorpt_coefficient_mu    0.283
_exptl_absorpt_correction_T_max  0.982
_exptl_absorpt_correction_T_min  0.912
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET)
(compiled Jan  5 2010,16:28:46)
Analytical numeric absorption correction using a multifaceted crystal
            model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.574
_exptl_crystal_description       needle
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.335
_refine_diff_density_min         -0.348
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.997
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     205
_refine_ls_number_reflns         3284
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.997
_refine_ls_R_factor_all          0.0507
_refine_ls_R_factor_gt           0.0367
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0651P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0957
_refine_ls_wR_factor_ref         0.0993
_reflns_number_gt                2522
_reflns_number_total             3284
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            jo2015328_si_002_2.cif
_cod_data_source_block           Otf
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4026629