#------------------------------------------------------------------------------
#$Date: 2021-04-05 18:19:57 +0300 (Mon, 05 Apr 2021) $
#$Revision: 263854 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/79/7157938.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7157938
loop_
_publ_author_name
'Goodwin, Rosemary J.'
'Blyth, Mitchell T.'
'Fung, Alfred K. K.'
'Smith, Leesa M.'
'Norcott, Philip L.'
'Tanovic, Sara'
'Coote, Michelle L.'
'White, Nicholas G.'
_publ_section_title
;
 Simple acyclic molecules containing a single charge-assisted O-H group
 can recognize anions in acetonitrile : water mixtures.
;
_journal_issue                   12
_journal_name_full               'Organic & 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         'C10 H10 N O, F6 P, H2 O'
_chemical_formula_sum            'C10 H12 F6 N O2 P'
_chemical_formula_weight         323.17
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -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                105.053(4)
_cell_angle_beta                 99.409(4)
_cell_angle_gamma                94.776(4)
_cell_formula_units_Z            2
_cell_length_a                   6.9715(3)
_cell_length_b                   8.8109(4)
_cell_length_c                   10.7517(4)
_cell_measurement_reflns_used    3808
_cell_measurement_temperature    150
_cell_measurement_theta_max      29.2
_cell_measurement_theta_min      3.59
_cell_volume                     623.68(5)
_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 Xcalibur'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.021
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            7730
_diffrn_reflns_theta_full        26.366
_diffrn_reflns_theta_max         26.366
_diffrn_reflns_theta_min         3.260
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.297
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_correction_T_min  0.93
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlisPro, (Agilent, 2011)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.721
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             327.999
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.69
_refine_diff_density_min         -0.46
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   0.9338
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2540
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0509
_refine_ls_R_factor_gt           0.0415
_refine_ls_shift/su_max          0.0004184
_refine_ls_shift/su_mean         0.0000322
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 
 [weight] = 1.0/[A₀*T₀(x)+A₁*T₁(x) ... +Aₙ₋₁]*Tₙ₋₁(x)] 
 where Ai are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)²]² 
 Ai are: 
 414. 659. 386. 150. 30.0 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1016
_refine_ls_wR_factor_gt          0.0916
_refine_ls_wR_factor_ref         0.1016
_reflns_limit_h_max              8
_reflns_limit_h_min              -8
_reflns_limit_k_max              10
_reflns_limit_k_min              -11
_reflns_limit_l_max              13
_reflns_limit_l_min              0
_reflns_number_gt                2120
_reflns_number_total             2549
_reflns_threshold_expression     I>2.0σ(I)
_oxford_diffrn_Wilson_B_factor   2.42
_oxford_diffrn_Wilson_scale      0.06
_oxford_refine_ls_r_factor_ref   0.0509
_oxford_refine_ls_scale          4.34(7)
_oxford_reflns_number_all        2540
_oxford_reflns_threshold_expression_ref I>-3.0\s(I)
_cod_data_source_file            d1ob00282a2.cif
_cod_data_source_block           2PF6
_cod_depositor_comments
;
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.
;
_cod_original_cell_volume        623.68(2)
_cod_original_sg_symbol_H-M      'P -1 '
_cod_original_formula_sum        'C10 H12 F6 N1 O2 P1'
_cod_database_code               7157938
_iucr_refine_instructions_details_constraints
;
#
# Punched on 19/09/17 at  9: 4:18
#
#LIST     12                                                                    
BLOCK 
CONT SCALE 
CONT N    (    1 ,X'S,U'S)  UNTIL O    (  101 ) 
CONT H    (  121 ,X'S)  UNTIL H    ( 1011 ) 
RIDE C   (   2,X'S) H   (  21,X'S) 
RIDE C   (   3,X'S) H   (  31,X'S) 
RIDE C   (   4,X'S) H   (  41,X'S) 
RIDE C   (   6,X'S) H   (  61,X'S) 
RIDE C   (   7,X'S) H   (  71,X'S) 
RIDE C   (   8,X'S) H   (  81,X'S) 
RIDE C   (  11,X'S) H   ( 113,X'S) H   ( 112,X'S) H   ( 111,X'S) 
END   
;
_iucr_refine_instructions_details_restraints
;                                                                          
#
# Punched on 19/09/17 at  9: 4:18
#
#LIST     16                                                                    
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 0.049, 0.002 = H(121,U[ISO]) 
REM       H ON O-HETRO ATOM 
DIST 0.82, 0.02 = 
CONT O ( 101) TO H(1012) 
CONT O ( 101) TO H(1011) 
REST 0.077, 0.002 = H(1012,U[ISO]) 
REST 0.077, 0.002 = H(1011,U[ISO]) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
N1 N 0.6998(3) 0.5331(2) 0.69879(17) 0.0231 1.0000 Uani . . . . . .
C2 C 0.6762(3) 0.6344(3) 0.8090(2) 0.0284 1.0000 Uani . . . . . .
C3 C 0.5151(4) 0.6153(3) 0.8669(2) 0.0308 1.0000 Uani . . . . . .
C4 C 0.3773(3) 0.4863(3) 0.8094(2) 0.0279 1.0000 Uani . . . . . .
C5 C 0.3953(3) 0.3777(3) 0.6915(2) 0.0241 1.0000 Uani . . . . . .
C6 C 0.2512(3) 0.2453(3) 0.6312(2) 0.0312 1.0000 Uani . . . . . .
C7 C 0.2688(4) 0.1420(3) 0.5161(2) 0.0345 1.0000 Uani . . . . . .
C8 C 0.4286(3) 0.1673(3) 0.4568(2) 0.0287 1.0000 Uani . . . . . .
C9 C 0.5739(3) 0.2937(3) 0.5123(2) 0.0230 1.0000 Uani . . . . . .
C10 C 0.5601(3) 0.4026(2) 0.6329(2) 0.0208 1.0000 Uani . . . . . .
C11 C 0.8853(3) 0.5647(3) 0.6531(2) 0.0344 1.0000 Uani . . . . . .
O12 O 0.7272(2) 0.3162(2) 0.45361(16) 0.0322 1.0000 Uani D . . . . .
P21 P 0.84800(8) 0.18527(6) 0.88368(5) 0.0229 1.0000 Uani . . . . . .
F21 F 0.6131(2) 0.1572(2) 0.86115(16) 0.0500 1.0000 Uani . . . . . .
F22 F 0.8634(2) 0.1987(2) 1.03604(15) 0.0515 1.0000 Uani . . . . . .
F23 F 0.8389(3) 0.36982(19) 0.91546(19) 0.0610 1.0000 Uani . . . . . .
F24 F 0.8302(2) 0.1744(2) 0.73181(14) 0.0450 1.0000 Uani . . . . . .
F25 F 0.8537(3) 0.00045(19) 0.8507(2) 0.0618 1.0000 Uani . . . . . .
F26 F 1.0812(2) 0.2135(2) 0.90578(15) 0.0437 1.0000 Uani . . . . . .
O101 O 0.2682(4) -0.0834(2) 0.7589(2) 0.0526 1.0000 Uani D . . . . .
H21 H 0.7769 0.7217 0.8505 0.0360 1.0000 Uiso R . . . . .
H31 H 0.5031 0.6902 0.9453 0.0372 1.0000 Uiso R . . . . .
H41 H 0.2675 0.4698 0.8492 0.0342 1.0000 Uiso R . . . . .
H61 H 0.1431 0.2293 0.6710 0.0385 1.0000 Uiso R . . . . .
H71 H 0.1728 0.0529 0.4741 0.0424 1.0000 Uiso R . . . . .
H81 H 0.4385 0.0937 0.3759 0.0354 1.0000 Uiso R . . . . .
H113 H 0.9511 0.4709 0.6465 0.0539 1.0000 Uiso R . . . . .
H112 H 0.8538 0.5848 0.5675 0.0539 1.0000 Uiso R . . . . .
H111 H 0.9635 0.6545 0.7172 0.0536 1.0000 Uiso R . . . . .
H121 H 0.719(5) 0.244(3) 0.387(2) 0.0497 1.0000 Uiso D . . . . .
H1012 H 0.206(5) -0.085(5) 0.815(3) 0.0781 1.0000 Uiso D . . . . .
H1011 H 0.354(5) -0.011(4) 0.791(4) 0.0782 1.0000 Uiso D . . . . .
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
F 0.0171 0.0103 3.5392 10.2825 2.6412 4.2944 1.5170 0.2615 1.0243 26.1476
0.2776 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
P 0.1023 0.0942 6.4345 1.9067 4.1791 27.1570 1.7800 0.5260 1.4908 68.1645
1.1149 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 . N1 . C10 . 121.34(19) yes
C2 . N1 . C11 . 116.24(19) yes
C10 . N1 . C11 . 122.40(18) yes
N1 . C2 . C3 . 122.6(2) yes
N1 . C2 . H21 . 118.0 no
C3 . C2 . H21 . 119.4 no
C2 . C3 . C4 . 118.6(2) yes
C2 . C3 . H31 . 120.2 no
C4 . C3 . H31 . 121.1 no
C3 . C4 . C5 . 120.4(2) yes
C3 . C4 . H41 . 119.7 no
C5 . C4 . H41 . 119.9 no
C4 . C5 . C6 . 120.4(2) yes
C4 . C5 . C10 . 119.6(2) yes
C6 . C5 . C10 . 120.0(2) yes
C5 . C6 . C7 . 119.9(2) yes
C5 . C6 . H61 . 119.5 no
C7 . C6 . H61 . 120.6 no
C6 . C7 . C8 . 120.3(2) yes
C6 . C7 . H71 . 120.9 no
C8 . C7 . H71 . 118.8 no
C7 . C8 . C9 . 122.0(2) yes
C7 . C8 . H81 . 119.2 no
C9 . C8 . H81 . 118.8 no
C8 . C9 . C10 . 118.89(19) yes
C8 . C9 . O12 . 121.17(19) yes
C10 . C9 . O12 . 119.94(19) yes
C5 . C10 . C9 . 118.83(19) yes
C5 . C10 . N1 . 117.36(18) yes
C9 . C10 . N1 . 123.81(18) yes
N1 . C11 . H113 . 107.3 no
N1 . C11 . H112 . 108.9 no
H113 . C11 . H112 . 110.5 no
N1 . C11 . H111 . 107.9 no
H113 . C11 . H111 . 110.6 no
H112 . C11 . H111 . 111.5 no
C9 . O12 . H121 . 110(2) no
F21 . P21 . F22 . 90.62(9) yes
F21 . P21 . F23 . 88.80(11) yes
F22 . P21 . F23 . 89.09(11) yes
F21 . P21 . F24 . 88.80(9) yes
F22 . P21 . F24 . 178.96(10) yes
F23 . P21 . F24 . 90.03(10) yes
F21 . P21 . F25 . 90.37(10) yes
F22 . P21 . F25 . 91.27(11) yes
F23 . P21 . F25 . 179.10(10) yes
F24 . P21 . F25 . 89.59(11) yes
F21 . P21 . F26 . 179.82(10) yes
F22 . P21 . F26 . 89.50(8) yes
F23 . P21 . F26 . 91.07(10) yes
F24 . P21 . F26 . 91.07(8) yes
F25 . P21 . F26 . 89.75(10) yes
H1012 . O101 . H1011 . 105(4) no
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
N1 . C2 . 1.329(3) yes
N1 . C10 . 1.392(3) yes
N1 . C11 . 1.487(3) yes
C2 . C3 . 1.389(3) yes
C2 . H21 . 0.955 no
C3 . C4 . 1.363(3) yes
C3 . H31 . 0.948 no
C4 . C5 . 1.407(3) yes
C4 . H41 . 0.954 no
C5 . C6 . 1.411(3) yes
C5 . C10 . 1.425(3) yes
C6 . C7 . 1.363(3) yes
C6 . H61 . 0.943 no
C7 . C8 . 1.401(3) yes
C7 . H71 . 0.947 no
C8 . C9 . 1.375(3) yes
C8 . H81 . 0.957 no
C9 . C10 . 1.422(3) yes
C9 . O12 . 1.353(3) yes
C11 . H113 . 0.970 no
C11 . H112 . 0.976 no
C11 . H111 . 0.960 no
O12 . H121 . 0.816(17) no
P21 . F21 . 1.6044(15) yes
P21 . F22 . 1.5965(16) yes
P21 . F23 . 1.5813(17) yes
P21 . F24 . 1.5941(15) yes
P21 . F25 . 1.5794(17) yes
P21 . F26 . 1.5927(15) yes
O101 . H1012 . 0.799(18) no
O101 . H1011 . 0.799(18) no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_site_symmetry_D
_geom_hbond_atom_site_label_H
_geom_hbond_site_symmetry_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
O12 . H121 . O101 2_656 173(3) 0.816 1.839 2.651(3) yes
loop_
_oxford_refln_omitted_index_h
_oxford_refln_omitted_index_k
_oxford_refln_omitted_index_l
_oxford_refln_omitted_flag
_oxford_refln_omitted_details
1 -2 2 x .
