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_7157940
_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.
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_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_absolute_configuration ad
_chemical_compound_source        synthesized
_chemical_formula_moiety         'C10 H10 N1 O1, Cl'
_chemical_formula_sum            'C10 H10 Cl N O'
_chemical_formula_weight         195.65
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 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                 97.057(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   5.17920(10)
_cell_length_b                   13.1666(3)
_cell_length_c                   6.8217(2)
_cell_measurement_reflns_used    2231
_cell_measurement_temperature    150
_cell_measurement_theta_max      73
_cell_measurement_theta_min      7
_cell_volume                     461.664(19)
_computing_cell_refinement       'CrysAlisPro, (Agilent, 2011)'
_computing_data_collection       'CrysAlisPro, (Agilent, 2011'
_computing_data_reduction        'CrysAlisPro, (Agilent, 2011)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'Superflip (Palatinus & Chapuis, 2007)'
_diffrn_ambient_temperature      150
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'Oxford Diffraction Supernova'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.017
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            3222
_diffrn_reflns_theta_full        73.681
_diffrn_reflns_theta_max         73.681
_diffrn_reflns_theta_min         6.539
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.302
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_correction_T_min  0.68
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlisPro, (Agilent, 2011)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.407
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             203.999
_exptl_crystal_size_max          0.69
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.30
_refine_diff_density_min         -0.26
_refine_ls_abs_structure_details 'Flack (1983), 776 Friedel-pairs'
_refine_ls_abs_structure_Flack   0.031(18)
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   0.9111
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     122
_refine_ls_number_reflns         1748
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0411
_refine_ls_R_factor_gt           0.0407
_refine_ls_shift/su_max          0.0006436
_refine_ls_shift/su_mean         0.0000564
_refine_ls_structure_factor_coef Fsqd
_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: 
 0.239E+04 0.405E+04 0.268E+04 0.124E+04 353. 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1067
_refine_ls_wR_factor_gt          0.1061
_refine_ls_wR_factor_ref         0.1067
_reflns_limit_h_max              6
_reflns_limit_h_min              -6
_reflns_limit_k_max              15
_reflns_limit_k_min              -16
_reflns_limit_l_max              8
_reflns_limit_l_min              0
_reflns_number_gt                1732
_reflns_number_total             1755
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   2.28
_oxford_diffrn_Wilson_scale      0.01
_oxford_refine_ls_r_factor_ref   0.0411
_oxford_refine_ls_scale          12.9(9)
_oxford_reflns_number_all        1748
_oxford_reflns_threshold_expression_ref I>-3.0\s(I)
_iucr_refine_instructions_details_constraints
;
BLOCK 
CONT SCALE 
CONT C    (    1 ,X'S,U'S)  UNTIL CL   (    1 ) 
CONT H    (  121 ,X'S) 
CONT ENANTIO 
RIDE C   (   1,X'S) H   (  13,X'S) H   (  12,X'S) H   (  11,X'S) 
RIDE C   (   3,X'S) H   (  31,X'S) 
RIDE C   (   4,X'S) H   (  41,X'S) 
RIDE C   (   5,X'S) H   (  51,X'S) 
RIDE C   (   8,X'S) H   (  81,X'S) 
RIDE C   (   9,X'S) H   (  91,X'S) 
RIDE C   (  10,X'S) H   ( 101,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       H ON O-HETRO ATOM 
DIST 0.82, 0.02 = 
CONT O ( 12) TO H(121) 
REST 0.065, 0.002 = H(121,U[ISO]) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
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_cod_data_source_file            d1ob00282a2.cif
_cod_data_source_block           2Cl
_cod_depositor_comments
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The following automatic conversions were performed:

data item '_atom_sites_solution_primary' value 'Other' was changed to
'other' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

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

 Adding full bibliography for 7157935--7157948.cif.
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_cod_original_cell_volume        461.664(14)
_cod_original_sg_symbol_H-M      'P 21 '
_cod_original_formula_sum        'C10 H10 Cl1 N1 O1'
_cod_database_code               7157940