#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/63/2226349.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2226349
loop_
_publ_author_name
'Fu, Xue-qun'
_publ_section_title
;
 4-Ethoxyanilinium hexafluorophosphate monohydrate
;
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1461
_journal_paper_doi               10.1107/S1600536810018404
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C8 H12 N O +, P F6 - , H2 O '
_chemical_formula_moiety         'C8 H12 N O, F6 P, H2 O '
_chemical_formula_sum            'C8 H14 F6 N O2 P'
_chemical_formula_weight         301.17
_chemical_name_systematic
;
4-Ethoxyanilinium hexafluorophosphate monohydrate
;
_space_group_IT_number           14
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 111.68(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   17.498(4)
_cell_length_b                   5.1236(10)
_cell_length_c                   14.793(3)
_cell_measurement_reflns_used    4774
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      27.7
_cell_measurement_theta_min      3.1
_cell_volume                     1232.4(5)
_computing_cell_refinement       'CrystalClear (Rigaku, 2005)'
_computing_data_collection       'CrystalClear (Rigaku, 2005)'
_computing_data_reduction        'CrystalClear (Rigaku, 2005)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'PRPKAPPA (Ferguson, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_detector_area_resol_mean 13.6612
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Rigaku SCXmini diffractometer'
_diffrn_measurement_method       'ω scans'
_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  0.0536
_diffrn_reflns_av_sigmaI/netI    0.0437
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            12124
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.09
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.294
_exptl_absorpt_correction_T_max  0.943
_exptl_absorpt_correction_T_min  0.900
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrystalClear; Rigaku, 2005)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.623
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.451
_refine_diff_density_min         -0.477
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         2820
_refine_ls_number_restraints     235
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0893
_refine_ls_R_factor_gt           0.0585
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0764P)²+0.6523P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1464
_refine_ls_wR_factor_ref         0.1638
_reflns_number_gt                1890
_reflns_number_total             2820
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            zq2040.cif
_cod_data_source_block           I
_cod_original_cell_volume        1232.4(4)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2226349
_cod_database_fobs_code          2226349
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N N1 0.15275(14) 0.3564(5) 0.42609(17) 0.0414(6) Uani d U 1 . .
H H1A 0.1427 0.4860 0.3832 0.050 Uiso d R 1 . .
H H1B 0.1304 0.3936 0.4697 0.050 Uiso d R 1 . .
H H1C 0.1311 0.2092 0.3953 0.050 Uiso d R 1 . .
O O1 0.49349(12) 0.2376(5) 0.60339(18) 0.0624(7) Uani d U 1 . .
C C1 0.40946(18) 0.2556(6) 0.5644(2) 0.0458(7) Uani d U 1 . .
C C4 0.24232(16) 0.3242(5) 0.47587(19) 0.0366(6) Uani d U 1 . .
C C3 0.29478(19) 0.4801(6) 0.4497(2) 0.0515(8) Uani d U 1 . .
H H3A 0.2739 0.6074 0.4021 0.062 Uiso calc R 1 . .
C C5 0.27196(18) 0.1368(7) 0.5450(2) 0.0497(8) Uani d U 1 . .
H H5A 0.2360 0.0333 0.5625 0.060 Uiso calc R 1 . .
C C6 0.35635(19) 0.1007(7) 0.5895(2) 0.0558(9) Uani d U 1 . .
H H6A 0.3769 -0.0286 0.6364 0.067 Uiso calc R 1 . .
C C2 0.37808(19) 0.4465(7) 0.4943(3) 0.0561(9) Uani d U 1 . .
H H2A 0.4137 0.5527 0.4773 0.067 Uiso calc R 1 . .
C C8 0.6217(2) 0.0478(10) 0.6954(3) 0.0783(12) Uani d U 1 . .
H H8A 0.6483 -0.0935 0.7380 0.117 Uiso calc R 1 . .
H H8B 0.6405 0.2108 0.7279 0.117 Uiso calc R 1 . .
H H8C 0.6347 0.0396 0.6378 0.117 Uiso calc R 1 . .
C C7 0.5304(2) 0.0266(8) 0.6678(3) 0.0632(10) Uani d U 1 . .
H H7A 0.5107 -0.1390 0.6359 0.076 Uiso calc R 1 . .
H H7B 0.5164 0.0372 0.7254 0.076 Uiso calc R 1 . .
O O1W 0.08195(12) 0.8613(5) 0.44539(16) 0.0473(5) Uani d D 1 . .
H H1WB 0.0467(16) 0.843(9) 0.3908(11) 0.086(15) Uiso d D 1 . .
H H1WA 0.071(2) 0.856(9) 0.4948(14) 0.086(15) Uiso d D 1 . .
P P1 0.11668(4) 0.96937(15) 0.18642(5) 0.0396(3) Uani d U 1 . .
F F3 0.0519(7) 1.103(3) 0.2240(8) 0.064(2) Uani d PU 0.73(3) A 1
F F5 0.1765(9) 0.833(3) 0.1430(10) 0.065(2) Uani d PU 0.73(3) A 1
F F4 0.0451(7) 0.782(2) 0.1246(9) 0.072(2) Uani d PU 0.73(3) A 1
F F1 0.0911(6) 1.1714(17) 0.0948(6) 0.0618(15) Uani d PU 0.73(3) A 1
F F2 0.1410(8) 0.783(2) 0.2777(7) 0.086(2) Uani d PU 0.73(3) A 1
F F6 0.1869(6) 1.169(2) 0.2477(7) 0.0704(18) Uani d PU 0.73(3) A 1
F F6' 0.1908(13) 1.081(6) 0.2715(16) 0.066(4) Uani d PU 0.27(3) A 2
F F4' 0.0396(15) 0.830(6) 0.1040(17) 0.053(4) Uani d PU 0.27(3) A 2
F F2' 0.1153(17) 0.730(5) 0.256(2) 0.070(4) Uani d PU 0.27(3) A 2
F F3' 0.0594(18) 1.160(7) 0.2229(19) 0.056(4) Uani d PU 0.27(3) A 2
F F5' 0.184(3) 0.796(8) 0.164(3) 0.062(4) Uani d PU 0.27(3) A 2
F F1' 0.1166(18) 1.168(5) 0.1154(19) 0.075(4) Uani d PU 0.27(3) A 2
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'
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C4 N1 H1A . . 109.5 ?
C4 N1 H1B . . 109.4 ?
H1A N1 H1B . . 109.5 ?
C4 N1 H1C . . 109.5 ?
H1A N1 H1C . . 109.5 ?
H1B N1 H1C . . 109.5 ?
C1 O1 C7 . . 118.8(3) ?
O1 C1 C6 . . 125.2(3) ?
O1 C1 C2 . . 115.5(3) ?
C6 C1 C2 . . 119.4(3) ?
C5 C4 C3 . . 120.9(3) ?
C5 C4 N1 . . 119.7(3) ?
C3 C4 N1 . . 119.4(3) ?
C2 C3 C4 . . 119.5(3) ?
C2 C3 H3A . . 120.2 ?
C4 C3 H3A . . 120.2 ?
C4 C5 C6 . . 119.6(3) ?
C4 C5 H5A . . 120.2 ?
C6 C5 H5A . . 120.2 ?
C1 C6 C5 . . 120.1(3) ?
C1 C6 H6A . . 119.9 ?
C5 C6 H6A . . 119.9 ?
C3 C2 C1 . . 120.4(3) ?
C3 C2 H2A . . 119.8 ?
C1 C2 H2A . . 119.8 ?
C7 C8 H8A . . 109.5 ?
C7 C8 H8B . . 109.5 ?
H8A C8 H8B . . 109.5 ?
C7 C8 H8C . . 109.5 ?
H8A C8 H8C . . 109.5 ?
H8B C8 H8C . . 109.5 ?
O1 C7 C8 . . 107.4(3) ?
O1 C7 H7A . . 110.2 ?
C8 C7 H7A . . 110.2 ?
O1 C7 H7B . . 110.2 ?
C8 C7 H7B . . 110.2 ?
H7A C7 H7B . . 108.5 ?
H1WB O1W H1WA . . 122(2) ?
F1' P1 F6' . . 96.0(11) ?
F1' P1 F4 . . 102.6(9) ?
F6' P1 F4 . . 161.3(10) ?
F1' P1 F5 . . 80.8(12) ?
F6' P1 F5 . . 90.7(10) ?
F4 P1 F5 . . 89.9(8) ?
F1' P1 F2 . . 164.6(8) ?
F6' P1 F2 . . 69.4(10) ?
F4 P1 F2 . . 91.9(4) ?
F5 P1 F2 . . 94.0(6) ?
F1' P1 F3 . . 98.1(12) ?
F6' P1 F3 . . 92.8(9) ?
F4 P1 F3 . . 87.1(6) ?
F5 P1 F3 . . 176.5(7) ?
F2 P1 F3 . . 87.9(6) ?
F1' P1 F6 . . 76.1(9) ?
F4 P1 F6 . . 177.8(5) ?
F5 P1 F6 . . 91.6(8) ?
F2 P1 F6 . . 89.7(3) ?
F3 P1 F6 . . 91.4(6) ?
F1' P1 F5' . . 92.5(15) ?
F6' P1 F5' . . 85.2(18) ?
F4 P1 F5' . . 91.5(18) ?
F2 P1 F5' . . 81.6(13) ?
F3 P1 F5' . . 169.4(13) ?
F6 P1 F5' . . 90.3(18) ?
F1' P1 F2' . . 174.5(15) ?
F6' P1 F2' . . 88.1(9) ?
F4 P1 F2' . . 73.3(9) ?
F5 P1 F2' . . 95.5(12) ?
F3 P1 F2' . . 85.4(12) ?
F6 P1 F2' . . 108.2(8) ?
F5' P1 F2' . . 84.1(17) ?
F1' P1 F4' . . 89.3(11) ?
F6' P1 F4' . . 174.7(12) ?
F5 P1 F4' . . 89.5(10) ?
F2 P1 F4' . . 105.3(9) ?
F3 P1 F4' . . 87.1(10) ?
F6 P1 F4' . . 164.9(9) ?
F5' P1 F4' . . 94.0(19) ?
F2' P1 F4' . . 86.7(10) ?
F1' P1 F3' . . 89.0(15) ?
F6' P1 F3' . . 86.7(13) ?
F4 P1 F3' . . 96.0(12) ?
F5 P1 F3' . . 169.1(14) ?
F2 P1 F3' . . 94.9(12) ?
F6 P1 F3' . . 82.3(12) ?
F5' P1 F3' . . 171.8(19) ?
F2' P1 F3' . . 94.9(17) ?
F4' P1 F3' . . 94.1(14) ?
F6' P1 F1 . . 109.3(11) ?
F4 P1 F1 . . 89.4(4) ?
F5 P1 F1 . . 87.8(5) ?
F2 P1 F1 . . 177.8(5) ?
F3 P1 F1 . . 90.3(5) ?
F6 P1 F1 . . 89.0(3) ?
F5' P1 F1 . . 100.2(13) ?
F2' P1 F1 . . 162.3(8) ?
F4' P1 F1 . . 75.9(10) ?
F3' P1 F1 . . 83.1(11) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
N1 C4 . 1.474(4) ?
N1 H1A . 0.8900 ?
N1 H1B . 0.8900 ?
N1 H1C . 0.8900 ?
O1 C1 . 1.370(4) ?
O1 C7 . 1.428(4) ?
C1 C6 . 1.373(4) ?
C1 C2 . 1.384(4) ?
C4 C5 . 1.358(4) ?
C4 C3 . 1.376(4) ?
C3 C2 . 1.371(4) ?
C3 H3A . 0.9300 ?
C5 C6 . 1.389(4) ?
C5 H5A . 0.9300 ?
C6 H6A . 0.9300 ?
C2 H2A . 0.9300 ?
C8 C7 . 1.500(5) ?
C8 H8A . 0.9600 ?
C8 H8B . 0.9600 ?
C8 H8C . 0.9600 ?
C7 H7A . 0.9700 ?
C7 H7B . 0.9700 ?
O1W H1WB . 0.821(10) ?
O1W H1WA . 0.82(3) ?
P1 F1' . 1.46(2) ?
P1 F6' . 1.546(18) ?
P1 F4 . 1.575(10) ?
P1 F5 . 1.578(13) ?
P1 F2 . 1.580(8) ?
P1 F3 . 1.590(11) ?
P1 F6 . 1.598(7) ?
P1 F5' . 1.60(4) ?
P1 F2' . 1.61(2) ?
P1 F4' . 1.61(3) ?
P1 F3' . 1.63(3) ?
P1 F1 . 1.632(7) ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N1 H1A F2' . 0.89 2.16 3.03(2) 167.2
N1 H1A F2 . 0.89 2.17 3.049(10) 169.0
N1 H1B F1 4_576 0.89 2.22 3.066(8) 157.6
N1 H1B F1' 4_576 0.89 2.28 3.09(3) 152.3
N1 H1C O1W 1_545 0.89 2.22 2.883(3) 130.8
N1 H1C F3 1_545 0.89 2.46 3.137(12) 133.3
N1 H1C F3' 1_545 0.89 2.40 3.01(3) 126.0
N1 H1C F6' 1_545 0.89 2.51 2.96(2) 112.4
O1W H1WB F3' 2_545 0.821(10) 2.20(3) 2.97(3) 156(4)
O1W H1WB F3 2_545 0.821(10) 2.28(3) 3.030(12) 152(4)
O1W H1WA F4 4_576 0.82(3) 2.241(19) 3.040(12) 164(4)
O1W H1WA F4' 4_576 0.82(3) 2.11(3) 2.88(2) 155(4)
O1W H1WA F5 4_576 0.82(3) 2.48(4) 2.951(16) 117(3)
C8 H8C Cg1 3_656 0.96 3.16 4.023(5) 150.06
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C7 O1 C1 C6 . . . . 6.9(5) ?
C7 O1 C1 C2 . . . . -172.9(3) ?
C5 C4 C3 C2 . . . . -0.2(5) ?
N1 C4 C3 C2 . . . . -178.5(3) ?
C3 C4 C5 C6 . . . . -0.5(5) ?
N1 C4 C5 C6 . . . . 177.8(3) ?
O1 C1 C6 C5 . . . . 180.0(3) ?
C2 C1 C6 C5 . . . . -0.3(5) ?
C4 C5 C6 C1 . . . . 0.7(5) ?
C4 C3 C2 C1 . . . . 0.7(5) ?
O1 C1 C2 C3 . . . . 179.3(3) ?
C6 C1 C2 C3 . . . . -0.4(5) ?
C1 O1 C7 C8 . . . . 177.4(3) ?
