#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/17/1501748.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_1501748
loop_
_publ_author_name
'Szafrański, Marek'
_publ_section_title
;
 Crystal structures, phase transitions, and pressure-induced
 ferroelectricity in [C(NH2)3]5SO4(SO3-OC2H5)2F.
;
_journal_issue                   34
_journal_name_full               'The journal of physical chemistry. B'
_journal_page_first              10277
_journal_page_last               10284
_journal_paper_doi               10.1021/jp204557d
_journal_volume                  115
_journal_year                    2011
_chemical_formula_moiety         'C9 H40 F N15 O12 S3'
_chemical_formula_sum            'C9 H40 F N15 O12 S3'
_chemical_formula_weight         665.74
_chemical_melting_point          450
_chemical_name_common
'pentaguanidinium diethoxysolfo-fluoro-sulfate'
_chemical_name_systematic
'pentaguanidinium diethoxysolfo-fluoro-sulfate'
_space_group_IT_number           62
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2n'
_symmetry_space_group_name_H-M   'P n m a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   20.171(4)
_cell_length_b                   10.563(2)
_cell_length_c                   14.348(3)
_cell_measurement_temperature    240.0(1)
_cell_volume                     3057.1(11)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      240.0(1)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'KUMA KM-4'
_diffrn_measurement_method       'THETA - 2THETA'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0657
_diffrn_reflns_limit_h_max       0
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       0
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            3175
_diffrn_reflns_theta_full        26.06
_diffrn_reflns_theta_max         26.06
_diffrn_reflns_theta_min         2.02
_exptl_absorpt_coefficient_mu    0.322
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.446
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1408
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.393
_refine_diff_density_min         -0.440
_refine_diff_density_rms         0.060
_refine_ls_extinction_coef       0.0012(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.991
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         3175
_refine_ls_number_restraints     22
_refine_ls_restrained_S_all      0.987
_refine_ls_R_factor_all          0.1142
_refine_ls_R_factor_gt           0.0430
_refine_ls_shift/su_max          0.181
_refine_ls_shift/su_mean         0.006
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0709P)²+1.3161P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1160
_refine_ls_wR_factor_ref         0.1378
_reflns_number_gt                1859
_reflns_number_total             3175
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jp204557d_si_003.cif
_cod_data_source_block           gfess_240
_cod_depositor_comments
;
The following automatic conversions were performed:
'_atom_site_symetry_multiplicity' tag replaced with
'_atom_site_symmetry_multiplicity'.

Automatic conversion script
Id: cif_correct_tags 1440 2010-10-19 06:21:57Z saulius 

The following automatic conversions were performed:

'_chemical_melting_point' value '450 K' was changed to '450' - the
value should be numeric and without a unit designator.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      Pnma
_cod_database_code               1501748
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z'
'x+1/2, -y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z'
'-x-1/2, y-1/2, z-1/2'
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
F1 F 0.0000 0.0000 0.0000 0.0673(9) Uani 1 2 d S
C1 C 0.28464(17) -0.0051(3) 0.9481(2) 0.0437(7) Uani 1 1 d .
N11 N 0.23623(16) 0.0761(3) 0.95742(19) 0.0632(9) Uani 1 1 d .
H11A H 0.2220 0.1181 0.9093 0.076 Uiso 1 1 calc R
H11B H 0.2182 0.0881 1.0118 0.076 Uiso 1 1 calc R
N12 N 0.31211(14) -0.0236(3) 0.86606(18) 0.0531(7) Uani 1 1 d .
H12A H 0.2980 0.0183 0.8178 0.064 Uiso 1 1 calc R
H12B H 0.3443 -0.0777 0.8601 0.064 Uiso 1 1 calc R
N13 N 0.30559(16) -0.0702(3) 1.02136(19) 0.0650(9) Uani 1 1 d .
H13A H 0.2871 -0.0588 1.0755 0.078 Uiso 1 1 calc R
H13B H 0.3378 -0.1243 1.0153 0.078 Uiso 1 1 calc R
C2 C -0.0984(2) 0.2500 -0.0683(3) 0.0493(12) Uani 1 2 d S
N21 N -0.12522(15) 0.1425(3) -0.0946(2) 0.0591(8) Uani 1 1 d .
H21A H -0.1606 0.1428 -0.1292 0.071 Uiso 1 1 calc R
H21B H -0.1076 0.0711 -0.0773 0.071 Uiso 1 1 calc R
N22 N -0.0449(2) 0.2500 -0.0150(3) 0.0712(14) Uani 1 2 d S
H22A H -0.0274 0.1787 0.0028 0.085 Uiso 0.50 1 calc PR
H22B H -0.0272 0.3213 0.0023 0.085 Uiso 0.50 1 calc PR
C3 C 0.04664(16) 0.0152(3) 0.7780(2) 0.0454(8) Uani 1 1 d .
N31 N 0.07305(15) 0.0774(3) 0.84795(19) 0.0604(8) Uani 1 1 d .
H31A H 0.1043 0.1324 0.8377 0.072 Uiso 1 1 calc R
H31B H 0.0593 0.0636 0.9045 0.072 Uiso 1 1 calc R
N32 N 0.06699(15) 0.0353(3) 0.69214(19) 0.0607(9) Uani 1 1 d .
H32A H 0.0982 0.0902 0.6813 0.073 Uiso 1 1 calc R
H32B H 0.0492 -0.0063 0.6462 0.073 Uiso 1 1 calc R
N33 N -0.00148(15) -0.0675(3) 0.7945(2) 0.0610(8) Uani 1 1 d .
H33A H -0.0152 -0.0800 0.8512 0.073 Uiso 1 1 calc R
H33B H -0.0193 -0.1091 0.7486 0.073 Uiso 1 1 calc R
S1 S 0.21492(5) 0.2500 0.72689(6) 0.0279(2) Uani 1 2 d S
O11 O 0.19009(15) 0.2500 0.82467(17) 0.0377(7) Uani 1 2 d S
O12 O 0.25542(10) 0.13604(19) 0.71139(13) 0.0403(5) Uani 1 1 d .
O13 O 0.15746(14) 0.2500 0.66471(17) 0.0326(6) Uani 1 2 d S
S2 S 0.14708(6) 0.2500 0.15122(8) 0.0427(3) Uani 1 2 d S
O21 O 0.12045(17) 0.2500 0.2435(2) 0.0562(9) Uani 1 2 d S
O22A O 0.1524(3) 0.1214(5) 0.1191(5) 0.0676(16) Uani 0.50 1 d P
O22B O 0.1168(3) 0.1662(6) 0.0842(4) 0.0623(15) Uani 0.50 1 d P
O23 O 0.2198(2) 0.3041(5) 0.1527(3) 0.0588(12) Uani 0.50 1 d P
C4 C 0.26416(10) 0.2500 0.20641(4) 0.101(2) Uani 1 2 d SD
H41 H 0.2566 0.1771 0.2496 0.121 Uiso 0.50 1 d PD
H42 H 0.2566 0.3229 0.2496 0.121 Uiso 0.50 1 d PD
C5 C 0.33496(10) 0.29466(15) 0.20742(15) 0.134(5) Uani 0.50 1 d PD
H51 H 0.35441(11) 0.2710(4) 0.14573(18) 0.201 Uiso 0.50 1 d PD
H52 H 0.35721(13) 0.2500 0.2603(2) 0.201 Uiso 1 2 d SD
H53 H 0.33358(13) 0.38843(12) 0.2168(3) 0.201 Uiso 0.50 1 d PD
S3 S 0.03159(6) 0.2500 0.44705(8) 0.0549(4) Uani 1 2 d S
O31 O 0.1003(2) 0.2500 0.4585(3) 0.0920(15) Uani 1 2 d S
O32B O -0.0059(3) 0.1854(7) 0.3877(4) 0.087(2) Uani 0.50 1 d P
O32A O 0.0283(3) 0.1067(6) 0.4198(5) 0.085(2) Uani 0.50 1 d P
O33 O 0.00451(18) 0.2500 0.5482(2) 0.0698(11) Uani 1 2 d S
C6 C -0.0662(2) 0.2203(3) 0.56189(15) 0.065(2) Uiso 0.50 1 d PD
H61 H -0.067(4) 0.1263(7) 0.554(5) 0.078 Uiso 0.50 1 d PD
H62 H -0.0900(7) 0.287(4) 0.525(4) 0.078 Uiso 0.50 1 d PD
C7 C -0.08091(11) 0.23122(19) 0.66435(16) 0.068(2) Uani 0.50 1 d PD
H71 H -0.12934(11) 0.2500 0.6699(3) 0.102 Uiso 1 2 d SD
H72 H -0.05281(15) 0.3019(4) 0.6886(2) 0.102 Uiso 0.50 1 d PD
H73 H -0.06893(18) 0.1479(3) 0.6929(2) 0.102 Uiso 0.50 1 d PD
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'
N N 0.0061 0.0033 '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'
S S 0.1246 0.1234 '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
N11 C1 N12 120.2(3) . .
N11 C1 N13 119.9(3) . .
N12 C1 N13 119.9(3) . .
N21 C2 N21 119.7(4) . 7_565
N21 C2 N22 120.2(2) . .
N21 C2 N22 120.2(2) 7_565 .
N31 C3 N32 120.6(3) . .
N31 C3 N33 119.4(3) . .
N32 C3 N33 120.1(3) . .
O13 S1 O12 110.35(10) . 7_565
O13 S1 O12 110.35(10) . .
O12 S1 O12 109.76(18) 7_565 .
O13 S1 O11 107.94(16) . .
O12 S1 O11 109.20(10) 7_565 .
O12 S1 O11 109.20(10) . .
O21 S2 O22A 109.0(2) . 7_565
O21 S2 O22A 109.0(2) . .
O22A S2 O22A 141.5(5) 7_565 .
O21 S2 O22B 117.3(3) . .
O22A S2 O22B 113.4(5) 7_565 .
O22A S2 O22B 40.4(3) . .
O21 S2 O22B 117.3(3) . 7_565
O22A S2 O22B 40.4(3) 7_565 7_565
O22A S2 O22B 113.4(5) . 7_565
O22B S2 O22B 75.7(5) . 7_565
O21 S2 O23 109.7(2) . .
O22A S2 O23 65.9(3) 7_565 .
O22A S2 O23 106.1(3) . .
O22B S2 O23 128.8(3) . .
O22B S2 O23 100.4(3) 7_565 .
O21 S2 O23 109.7(2) . 7_565
O22A S2 O23 106.1(3) 7_565 7_565
O22A S2 O23 65.9(3) . 7_565
O22B S2 O23 100.4(3) . 7_565
O22B S2 O23 128.8(3) 7_565 7_565
O23 S2 O23 42.6(4) . 7_565
O22B O22A S2 70.0(5) . .
O22B O22A O23 121.1(6) . 7_565
S2 O22A O23 61.0(3) . 7_565
O22A O22B S2 69.6(5) . .
O22A O22B O22B 118.4(5) . 7_565
S2 O22B O22B 52.2(3) . 7_565
O23 O23 C4 64.2(2) 7_565 .
O23 O23 S2 68.70(18) 7_565 .
C4 O23 S2 119.0(3) . .
O23 O23 O22A 118.6(3) 7_565 7_565
C4 O23 O22A 161.0(4) . 7_565
S2 O23 O22A 53.1(2) . 7_565
O23 C4 O23 51.7(4) 7_565 .
O23 C4 C5 142.2(2) 7_565 .
O23 C4 C5 121.1(2) . .
O23 C4 C5 121.1(2) 7_565 7_565
O23 C4 C5 142.2(2) . 7_565
C5 C4 C5 36.56(13) . 7_565
C5 C5 C4 71.72(7) 7_565 .
O32B S3 O32B 61.9(7) . 7_565
O32B S3 O31 129.9(3) . .
O32B S3 O31 129.9(3) 7_565 .
O32B S3 O33 113.5(3) . .
O32B S3 O33 113.5(3) 7_565 .
O31 S3 O33 103.9(2) . .
O32B S3 O32A 108.2(6) . 7_565
O32B S3 O32A 47.0(3) 7_565 7_565
O31 S3 O32A 94.1(3) . 7_565
O33 S3 O32A 102.7(3) . 7_565
O32B S3 O32A 47.0(3) . .
O32B S3 O32A 108.2(6) 7_565 .
O31 S3 O32A 94.1(3) . .
O33 S3 O32A 102.7(3) . .
O32A S3 O32A 150.6(6) 7_565 .
O32A O32B S3 77.2(5) . .
O32A O32B O32B 135.1(4) . 7_565
S3 O32B O32B 59.1(4) . 7_565
O32B O32A S3 55.8(4) . .
C6 O33 C6 24.5(2) 7_565 .
C6 O33 S3 117.8(2) 7_565 .
C6 O33 S3 117.8(2) . .
C6 C6 O33 77.73(12) 7_565 .
C6 C6 C7 85.62(13) 7_565 .
O33 C6 C7 107.8(2) . .
C6 C6 C7 71.16(13) 7_565 7_565
O33 C6 C7 103.7(2) . 7_565
C7 C6 C7 14.46(14) . 7_565
C7 C7 C6 94.38(13) 7_565 .
C7 C7 C6 71.16(13) 7_565 7_565
C6 C7 C6 23.2(2) . 7_565
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 N11 1.306(4) .
C1 N12 1.316(4) .
C1 N13 1.325(4) .
C2 N21 1.313(4) .
C2 N21 1.313(4) 7_565
C2 N22 1.322(6) .
C3 N31 1.312(4) .
C3 N32 1.316(4) .
C3 N33 1.327(4) .
S1 O13 1.463(3) .
S1 O12 1.472(2) 7_565
S1 O12 1.472(2) .
S1 O11 1.490(3) .
S2 O21 1.429(3) .
S2 O22A 1.438(5) 7_565
S2 O22A 1.438(5) .
S2 O22B 1.442(6) .
S2 O22B 1.442(6) 7_565
S2 O23 1.574(5) .
S2 O23 1.574(5) 7_565
O22A O22B 0.995(7) .
O22A O23 1.643(8) 7_565
O22B O22B 1.769(12) 7_565
O23 O23 1.144(10) 7_565
O23 C4 1.312(5) .
O23 O22A 1.643(8) 7_565
C4 O23 1.312(5) 7_565
C4 C5 1.5040(4) .
C4 C5 1.5040(4) 7_565
C5 C5 0.943(3) 7_565
S3 O32B 1.328(5) .
S3 O32B 1.328(5) 7_565
S3 O31 1.395(4) .
S3 O33 1.550(4) .
S3 O32A 1.565(6) 7_565
S3 O32A 1.565(6) .
O32B O32A 1.174(8) .
O32B O32B 1.365(16) 7_565
O33 C6 1.474(5) 7_565
O33 C6 1.474(5) .
C6 C6 0.627(6) 7_565
C6 C7 1.5041(4) .
C6 C7 1.5845(12) 7_565
C7 C7 0.397(4) 7_565
C7 C6 1.5845(12) 7_565
