#------------------------------------------------------------------------------
#$Date: 2016-03-25 11:42:00 +0200 (Fri, 25 Mar 2016) $
#$Revision: 179803 $
#$URL: svn://www.crystallography.net/cod/cif/7/00/99/7009937.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_7009937
loop_
_publ_author_name
'Rajendra P. Singh'
'Brendan Twamley'
'Jean'ne M. Shreeve'
_publ_section_title
;
 The first crystal and molecular structures of hydrated
 bis(n-perfluoroalkyl)phosphinic acids [H3O]+[(Rf)2PO2]−
 (Rf = C6F13, C7F15 or C8F17)
;
_journal_issue                   22
_journal_name_full               'J. Chem. Soc., Dalton Trans.'
_journal_page_first              4089
_journal_page_last               4092
_journal_paper_doi               10.1039/b004482m
_journal_year                    2000
_chemical_formula_sum            'C14 H3 F30 O3 P'
_chemical_formula_weight         820.13
_chemical_name_common            '[C14F30PO2]-[H3O]+'
_chemical_name_systematic
; 
? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                78.0740(10)
_cell_angle_beta                 89.2660(10)
_cell_angle_gamma                82.5320(10)
_cell_formula_units_Z            2
_cell_length_a                   6.1951(2)
_cell_length_b                   11.1604(3)
_cell_length_c                   18.7348(5)
_cell_measurement_reflns_used    4978
_cell_measurement_temperature    203(2)
_cell_measurement_theta_max      25.00
_cell_measurement_theta_min      1.11
_cell_volume                     1256.48(6)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL v. 5.10'
_computing_molecular_graphics    'XP, Bruker SHELXTL v. 5.10'
_computing_publication_material  'XCIF, Bruker SHELXTL v. 5.10'
_computing_structure_refinement  'XL, Bruker SHELXTL v. 5.10'
_computing_structure_solution    'XS, Bruker SHELXTL v. 5.10'
_diffrn_ambient_temperature      203(2)
_diffrn_measured_fraction_theta_full 0.976
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_device_type  'Siemens SMART 1000'
_diffrn_measurement_method       /w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0379
_diffrn_reflns_av_sigmaI/netI    0.0560
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            12430
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.11
_diffrn_standards_decay_%        '< 0.01%'
_diffrn_standards_number         '50 frames remeasured'
_exptl_absorpt_coefficient_mu    0.353
_exptl_absorpt_correction_T_max  0.9826
_exptl_absorpt_correction_T_min  0.7779
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
;SADABS: an empirical absorption program by G.M. Sheldrick
using the method described by Blessing, R.H.; Acta Cryst.
A51, 1995, 33.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    2.168
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.75
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.548
_refine_diff_density_min         -0.329
_refine_diff_density_rms         0.070
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     453
_refine_ls_number_reflns         4329
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.0951
_refine_ls_R_factor_gt           0.0641
_refine_ls_shift/su_max          0.011
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0579P)²+1.9556P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1405
_refine_ls_wR_factor_ref         0.1567
_reflns_number_gt                3120
_reflns_number_total             4329
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b004482m.txt
_cod_data_source_block           bt122
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/adriana/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from
2010-06-29.

'_exptl_absorpt_correction_type' value 'Empirical' changed to
'empirical' according to
'/home/adriana/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1555 2011-01-17 13:19:09Z saulius 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7009937
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_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P 0.32628(17) 0.23086(9) 0.45924(6) 0.0265(3) Uani 1 1 d . . .
O1 O 0.1644(4) 0.1453(2) 0.48590(15) 0.0307(7) Uani 1 1 d . . .
O2 O 0.5086(5) 0.1978(3) 0.41162(16) 0.0385(7) Uani 1 1 d . . .
O3 O 0.8542(5) 0.0675(3) 0.42120(19) 0.0411(8) Uani 1 1 d D . .
F1 F -0.0094(4) 0.4067(2) 0.44244(13) 0.0489(7) Uani 1 1 d . . .
F2 F 0.3010(5) 0.4713(2) 0.41015(15) 0.0556(8) Uani 1 1 d . . .
F3 F 0.0574(5) 0.2703(2) 0.32908(14) 0.0505(7) Uani 1 1 d . . .
F4 F 0.3105(4) 0.3842(3) 0.29168(14) 0.0566(8) Uani 1 1 d . . .
F5 F -0.0105(5) 0.5889(2) 0.30760(16) 0.0615(9) Uani 1 1 d . . .
F6 F -0.2415(4) 0.4592(3) 0.31519(14) 0.0560(8) Uani 1 1 d . . .
F7 F 0.1213(5) 0.5568(4) 0.18152(17) 0.0848(12) Uani 1 1 d . . .
F8 F -0.0259(7) 0.3905(3) 0.18942(17) 0.0864(13) Uani 1 1 d . . .
F9 F -0.3027(7) 0.6752(3) 0.1962(2) 0.0975(14) Uani 1 1 d . . .
F10 F -0.4150(5) 0.5120(4) 0.17947(19) 0.0929(13) Uani 1 1 d . . .
F11 F -0.1001(8) 0.7069(5) 0.0738(3) 0.149(2) Uani 1 1 d . . .
F12 F -0.1500(8) 0.5288(5) 0.05674(19) 0.132(2) Uani 1 1 d . . .
F13 F -0.4076(7) 0.7179(6) -0.0243(2) 0.141(2) Uani 1 1 d . A .
F14A F -0.571(3) 0.750(3) 0.0780(8) 0.114(7) Uani 0.61(6) 1 d P A 1
F14B F -0.473(12) 0.790(2) 0.054(3) 0.14(2) Uani 0.39(6) 1 d P A 2
F15 F -0.5768(8) 0.6023(6) 0.0459(2) 0.1243(17) Uani 1 1 d . A .
F16 F 0.2967(5) 0.3537(2) 0.56749(14) 0.0529(8) Uani 1 1 d . . .
F17 F 0.6190(4) 0.3316(2) 0.52076(14) 0.0487(7) Uani 1 1 d . . .
F18 F 0.3332(4) 0.1229(3) 0.63439(14) 0.0476(7) Uani 1 1 d . . .
F19 F 0.6066(5) 0.0723(2) 0.56842(13) 0.0461(7) Uani 1 1 d . . .
F20 F 0.6031(5) 0.2803(2) 0.68274(14) 0.0506(7) Uani 1 1 d . . .
F21 F 0.8670(4) 0.1832(3) 0.63122(14) 0.0514(7) Uani 1 1 d . . .
F22 F 0.5170(4) 0.0829(3) 0.76974(14) 0.0574(8) Uani 1 1 d . . .
F23 F 0.6841(5) -0.0381(2) 0.70536(15) 0.0607(9) Uani 1 1 d . . .
F24 F 0.9296(6) 0.1618(3) 0.78499(19) 0.0901(13) Uani 1 1 d . . .
F25 F 1.0625(5) 0.0068(4) 0.73917(17) 0.0850(12) Uani 1 1 d . . .
F26 F 0.7611(6) 0.0203(4) 0.89431(17) 0.0850(11) Uani 1 1 d . . .
F27 F 0.8070(6) -0.1361(3) 0.84328(17) 0.0775(10) Uani 1 1 d . . .
F28 F 1.0807(6) -0.1362(4) 0.9566(2) 0.1070(15) Uani 1 1 d . . .
F29 F 1.2115(7) 0.0159(4) 0.8930(2) 0.1106(16) Uani 1 1 d . . .
F30 F 1.2344(8) -0.1502(5) 0.8565(3) 0.1235(18) Uani 1 1 d . . .
C1 C 0.1778(7) 0.3807(4) 0.4089(2) 0.0330(10) Uani 1 1 d . . .
C2 C 0.1262(7) 0.3794(4) 0.3294(2) 0.0320(9) Uani 1 1 d . . .
C3 C -0.0474(7) 0.4831(4) 0.2899(2) 0.0343(10) Uani 1 1 d . . .
C4 C -0.0500(7) 0.4998(4) 0.2066(2) 0.0415(11) Uani 1 1 d . . .
C5 C -0.2512(8) 0.5773(4) 0.1670(3) 0.0432(11) Uani 1 1 d . . .
C6 C -0.2359(10) 0.6202(7) 0.0853(3) 0.0688(17) Uani 1 1 d . A .
C7 C -0.4392(12) 0.6835(8) 0.0435(4) 0.078(2) Uani 1 1 d . . .
C8 C 0.4428(7) 0.2746(4) 0.5409(2) 0.0320(10) Uani 1 1 d . . .
C9 C 0.5124(7) 0.1612(4) 0.6018(2) 0.0298(9) Uani 1 1 d . . .
C10 C 0.6709(7) 0.1752(4) 0.6608(2) 0.0329(10) Uani 1 1 d . . .
C11 C 0.6884(7) 0.0672(4) 0.7285(2) 0.0344(10) Uani 1 1 d . . .
C12 C 0.8950(8) 0.0527(5) 0.7759(3) 0.0457(12) Uani 1 1 d . . .
C13 C 0.8910(9) -0.0354(5) 0.8509(3) 0.0532(13) Uani 1 1 d . . .
C14 C 1.1079(11) -0.0764(7) 0.8903(3) 0.0749(19) Uani 1 1 d . . .
H1 H 0.845(13) 0.000(4) 0.451(3) 0.130(18) Uiso 1 1 d D . .
H2 H 0.961(9) 0.091(7) 0.440(4) 0.130(18) Uiso 1 1 d D . .
H3 H 0.728(7) 0.112(6) 0.418(4) 0.130(18) Uiso 1 1 d D . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 P1 O2 121.73(17) . . ?
O1 P1 C1 108.55(17) . . ?
O2 P1 C1 105.94(18) . . ?
O1 P1 C8 107.66(17) . . ?
O2 P1 C8 108.50(18) . . ?
C1 P1 C8 102.90(18) . . ?
P1 O2 H3 139(3) . . ?
H1 O3 H2 100(7) . . ?
H1 O3 H3 108(7) . . ?
H2 O3 H3 119(7) . . ?
F1 C1 F2 108.1(3) . . ?
F1 C1 C2 108.5(3) . . ?
F2 C1 C2 108.8(3) . . ?
F1 C1 P1 109.6(3) . . ?
F2 C1 P1 108.8(3) . . ?
C2 C1 P1 112.9(3) . . ?
F4 C2 F3 107.8(3) . . ?
F4 C2 C1 108.5(3) . . ?
F3 C2 C1 106.9(3) . . ?
F4 C2 C3 108.5(3) . . ?
F3 C2 C3 108.3(3) . . ?
C1 C2 C3 116.5(3) . . ?
F6 C3 F5 107.4(4) . . ?
F6 C3 C4 109.3(4) . . ?
F5 C3 C4 109.1(3) . . ?
F6 C3 C2 108.5(3) . . ?
F5 C3 C2 107.9(3) . . ?
C4 C3 C2 114.5(4) . . ?
F8 C4 F7 108.3(4) . . ?
F8 C4 C5 109.1(4) . . ?
F7 C4 C5 106.8(4) . . ?
F8 C4 C3 109.1(4) . . ?
F7 C4 C3 107.4(4) . . ?
C5 C4 C3 115.9(4) . . ?
F10 C5 F9 106.6(4) . . ?
F10 C5 C6 107.5(4) . . ?
F9 C5 C6 108.6(4) . . ?
F10 C5 C4 108.1(4) . . ?
F9 C5 C4 108.8(4) . . ?
C6 C5 C4 116.8(4) . . ?
F12 C6 F11 107.9(6) . . ?
F12 C6 C7 110.0(6) . . ?
F11 C6 C7 103.8(6) . . ?
F12 C6 C5 109.7(5) . . ?
F11 C6 C5 106.9(5) . . ?
C7 C6 C5 118.0(5) . . ?
F14B C7 F13 94(3) . . ?
F14B C7 F14A 40(3) . . ?
F13 C7 F14A 121.0(12) . . ?
F14B C7 F15 129(4) . . ?
F13 C7 F15 103.2(6) . . ?
F14A C7 F15 92.0(16) . . ?
F14B C7 C6 107.9(17) . . ?
F13 C7 C6 112.9(6) . . ?
F14A C7 C6 115.1(8) . . ?
F15 C7 C6 108.6(6) . . ?
F16 C8 F17 107.9(3) . . ?
F16 C8 C9 109.0(3) . . ?
F17 C8 C9 108.2(3) . . ?
F16 C8 P1 110.4(3) . . ?
F17 C8 P1 109.2(3) . . ?
C9 C8 P1 112.0(3) . . ?
F18 C9 F19 107.8(3) . . ?
F18 C9 C10 108.4(3) . . ?
F19 C9 C10 107.9(3) . . ?
F18 C9 C8 108.3(3) . . ?
F19 C9 C8 106.2(3) . . ?
C10 C9 C8 117.9(3) . . ?
F21 C10 F20 108.6(3) . . ?
F21 C10 C9 108.3(3) . . ?
F20 C10 C9 108.4(3) . . ?
F21 C10 C11 109.4(3) . . ?
F20 C10 C11 108.4(3) . . ?
C9 C10 C11 113.6(3) . . ?
F22 C11 F23 108.1(4) . . ?
F22 C11 C12 108.5(4) . . ?
F23 C11 C12 107.9(4) . . ?
F22 C11 C10 108.8(3) . . ?
F23 C11 C10 108.2(3) . . ?
C12 C11 C10 115.2(3) . . ?
F24 C12 F25 108.6(4) . . ?
F24 C12 C11 108.8(4) . . ?
F25 C12 C11 107.5(4) . . ?
F24 C12 C13 109.5(4) . . ?
F25 C12 C13 107.2(4) . . ?
C11 C12 C13 115.1(4) . . ?
F26 C13 F27 107.5(5) . . ?
F26 C13 C14 106.9(5) . . ?
F27 C13 C14 108.0(5) . . ?
F26 C13 C12 108.6(4) . . ?
F27 C13 C12 109.4(4) . . ?
C14 C13 C12 116.1(5) . . ?
F29 C14 F28 108.9(6) . . ?
F29 C14 F30 106.7(6) . . ?
F28 C14 F30 108.0(6) . . ?
F29 C14 C13 111.9(6) . . ?
F28 C14 C13 110.5(5) . . ?
F30 C14 C13 110.6(6) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P1 O1 1.485(3) . ?
P1 O2 1.487(3) . ?
P1 C1 1.872(4) . ?
P1 C8 1.878(4) . ?
O2 H3 1.55(2) . ?
O3 H1 0.84(2) . ?
O3 H2 0.85(2) . ?
O3 H3 0.86(2) . ?
F1 C1 1.339(5) . ?
F2 C1 1.347(5) . ?
F3 C2 1.343(5) . ?
F4 C2 1.336(5) . ?
F5 C3 1.338(5) . ?
F6 C3 1.326(5) . ?
F7 C4 1.338(5) . ?
F8 C4 1.314(6) . ?
F9 C5 1.321(6) . ?
F10 C5 1.316(6) . ?
F11 C6 1.346(8) . ?
F12 C6 1.298(7) . ?
F13 C7 1.271(7) . ?
F14A C7 1.292(17) . ?
F14B C7 1.24(2) . ?
F15 C7 1.316(9) . ?
F16 C8 1.345(5) . ?
F17 C8 1.345(5) . ?
F18 C9 1.336(5) . ?
F19 C9 1.347(4) . ?
F20 C10 1.338(5) . ?
F21 C10 1.335(5) . ?
F22 C11 1.319(5) . ?
F23 C11 1.337(5) . ?
F24 C12 1.308(6) . ?
F25 C12 1.343(6) . ?
F26 C13 1.326(6) . ?
F27 C13 1.332(6) . ?
F28 C14 1.303(6) . ?
F29 C14 1.292(8) . ?
F30 C14 1.316(8) . ?
C1 C2 1.530(6) . ?
C2 C3 1.545(6) . ?
C3 C4 1.532(6) . ?
C4 C5 1.527(6) . ?
C5 C6 1.513(7) . ?
C6 C7 1.504(8) . ?
C8 C9 1.538(6) . ?
C9 C10 1.533(6) . ?
C10 C11 1.553(6) . ?
C11 C12 1.539(6) . ?
C12 C13 1.541(7) . ?
C13 C14 1.512(8) . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O3 H1 O1 0.84(2) 1.81(2) 2.653(4) 178(8) 2_656
O3 H1 O3 0.84(2) 2.97(7) 3.442(7) 118(6) 2_756
O3 H2 O1 0.85(2) 1.77(2) 2.616(4) 174(8) 1_655
O3 H2 F19 0.85(2) 3.06(7) 3.488(4) 113(6) 2_756
O3 H3 O2 0.86(2) 1.55(2) 2.413(4) 177(9) .
