Simple acyclic molecules containing a single charge-assisted O-H group can recognize anions in acetonitrile : water mixtures.
Goodwin, Rosemary J.; Blyth, Mitchell T.; Fung, Alfred K. K.; Smith, Leesa M.; Norcott, Philip L.; Tanovic, Sara; Coote, Michelle L.; White, Nicholas G.; Organic & biomolecular chemistry 19 (2021) 2794–2803; doi:10.1039/d1ob00282a

data_7157948
_publ_section_title
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 Simple acyclic molecules containing a single charge-assisted O-H group
 can recognize anions in acetonitrile&#x2009;:&#x2009;water mixtures.
;
_journal_issue                   12
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              2794
_journal_page_last               2803
_journal_paper_doi               10.1039/d1ob00282a
_journal_volume                  19
_journal_year                    2021
_chemical_compound_source        synthesized
_chemical_formula_moiety         'C9 H17 N2, F6 P1'
_chemical_formula_sum            'C9 H17 F6 N2 P'
_chemical_formula_weight         298.21
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_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     other
_audit_update_record
;
2020-12-16 deposited with the CCDC.	2021-03-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 103.840(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.294(3)
_cell_length_b                   26.438(2)
_cell_length_c                   7.670(4)
_cell_measurement_reflns_used    11327
_cell_measurement_temperature    100
_cell_measurement_theta_max      31.8
_cell_measurement_theta_min      2.84
_cell_volume                     1239.2(9)
_computing_cell_refinement       'XDS (Kabsch, 1993)'
_computing_data_collection       'BluIce (McPhillips, 2002)'
_computing_data_reduction        'XDS (Kabsch, 1993)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.947
_diffrn_measured_fraction_theta_max 0.814
_diffrn_measurement_device_type  'ADSC Quantum 210r'
_diffrn_measurement_method       'Omega scan'
_diffrn_radiation_monochromator  'Silicon Double Crystal'
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.710918
_diffrn_reflns_av_R_equivalents  0.021
_diffrn_reflns_av_unetI/netI     0.021
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       39
_diffrn_reflns_limit_k_min       -39
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            12339
_diffrn_reflns_theta_full        25.123
_diffrn_reflns_theta_max         31.801
_diffrn_reflns_theta_min         2.842
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.282
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.598
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.46
_refine_diff_density_min         -0.31
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   0.9964
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     167
_refine_ls_number_reflns         3445
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0366
_refine_ls_R_factor_gt           0.0346
_refine_ls_shift/su_max          0.0021061
_refine_ls_shift/su_mean         0.0000821
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[\s^2^(F^2^) + ( 0.04P)^2^ + 0.86P] 
 ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0873
_refine_ls_wR_factor_gt          0.0860
_refine_ls_wR_factor_ref         0.0873
_reflns_limit_h_max              8
_reflns_limit_h_min              -8
_reflns_limit_k_max              39
_reflns_limit_k_min              0
_reflns_limit_l_max              11
_reflns_limit_l_min              0
_reflns_number_gt                3228
_reflns_number_total             3445
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   0.00
_oxford_diffrn_Wilson_scale      0.00
_oxford_refine_ls_r_factor_ref   0.0366
_oxford_refine_ls_scale          1.391(6)
_oxford_reflns_number_all        3445
_iucr_refine_instructions_details_constraints
;
BLOCK 
CONT SCALE 
CONT P    (     1 ,X'S,U'S)  UNTIL C    (    18 ) 
CONT H    (    91 ,X'S,U[ISO]) 
RIDE C   (  10,X'S) H   ( 102,X'S) H   ( 101,X'S) 
RIDE C   (  12,X'S) H   ( 122,X'S) H   ( 121,X'S) 
RIDE C   (  13,X'S) H   ( 132,X'S) H   ( 131,X'S) 
RIDE C   (  14,X'S) H   ( 142,X'S) H   ( 141,X'S) 
RIDE C   (  15,X'S) H   ( 152,X'S) H   ( 151,X'S) 
RIDE C   (  16,X'S) H   ( 162,X'S) H   ( 161,X'S) 
RIDE C   (  17,X'S) H   ( 172,X'S) H   ( 171,X'S) 
RIDE C   (  18,X'S) H   ( 182,X'S) H   ( 181,X'S) 
END                                                                             
;
_iucr_refine_instructions_details_restraints
;
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM NO H  NO #H U MULT   DIST 
REM C-H 
REM >4           1.5    .96 DISORDER 
REM 1      1     1.2    .93 C C-H (ACETYLENE) 
REM 1      2     1.2    .93 C-C(H)-C 
REM 1      3     1.2    .98 (C)3-C-H 
REM 2      1     1.2    .93 C=C-H(2) 
REM 2      2     1.2    .97 (C)2-C-(H)2 
REM 3      1     1.5    .96 C-C-(H)3 
REM N-H 
REM >4           1.5    .89 DISORDER 
REM 1      1     1.2    .86 N-N/H 
REM 1      2     1.2    .86 (C)2-N-H 
REM 1      3     1.2    .89 (C)3-N-H 
REM 2      1     1.2    .86 C-N-(H)2 
REM 2      2     1.2    .89 (C)2-N-(H)2 
REM 3      1     1.2    .89 C-H-(H)3 
REM O-H 
REM 1      1     1.5    .82 O-H 
REM 
REM DIST      ESD = 0.02 
REM VIB       ESD = 0.002 
REM ANGLE     ESD = 2.0 
REM 
REM TO ACTIVATE THE VIB RESTRAINTS, REMOVE LEADING REM 
REM            H1-N-R2 
DIST 0.86, 0.02 = 
CONT N ( 9) TO H(91) 
REST 0.023, 0.002 = H(91,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(91) TO N ( 9) TO C(11) 
CONT H(91) TO N ( 9) TO C(18) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
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_cod_data_source_file            d1ob00282a2.cif
_cod_data_source_block           DBUHPF6
_cod_depositor_comments
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The following automatic conversions were performed:

data item '_exptl_crystal_density_meas' value 'not measured' was
changed to '?' -- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 

 Adding full bibliography for 7157935--7157948.cif.
;
_cod_original_cell_volume        1239.24(5)
_cod_original_sg_symbol_H-M      'P 1 21/c 1 '
_cod_original_formula_sum        'C9 H17 F6 N2 P1'
_cod_database_code               7157948
_oxford_refine_reflns_threshold_expression_ref I>-3.0\s(I)