#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/47/2234785.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_2234785
loop_
_publ_author_name
'Xue, Hua Yu'
'Wang, Shi Juan'
_publ_section_title
;
 4-[(2'-Cyanobiphenyl-4-yl)methyl]morpholin-4-ium hexafluoridophosphate
;
_journal_coeditor_code           RZ2727
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1382
_journal_paper_doi               10.1107/S160053681201358X
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C18 H19 N2 O +, P F6-'
_chemical_formula_moiety         'C18 H19 N2 O +, F6 P -'
_chemical_formula_sum            'C18 H19 F6 N2 O P'
_chemical_formula_weight         424.32
_chemical_name_systematic
;
4-[(2'-Cyanobiphenyl-4-yl)methyl]morpholin-4-ium hexafluoridophosphate
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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                 91.07(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   24.912(11)
_cell_length_b                   10.757(5)
_cell_length_c                   14.925(7)
_cell_measurement_reflns_used    4512
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.390
_cell_measurement_theta_min      2.6251
_cell_volume                     3999(3)
_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  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 13.6612
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Rigaku Mercury2'
_diffrn_measurement_method       CCD_Profile_fitting
_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  0.0520
_diffrn_reflns_av_sigmaI/netI    0.0374
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            21155
_diffrn_reflns_theta_full        27.39
_diffrn_reflns_theta_max         27.39
_diffrn_reflns_theta_min         2.06
_exptl_absorpt_coefficient_mu    0.202
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8130
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrystalClear; Rigaku, 2005)'
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.410
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             1744
_exptl_crystal_size_max          0.2000
_exptl_crystal_size_mid          0.2000
_exptl_crystal_size_min          0.2000
_refine_diff_density_max         0.158
_refine_diff_density_min         -0.169
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.191
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     308
_refine_ls_number_reflns         4512
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.191
_refine_ls_R_factor_all          0.1171
_refine_ls_R_factor_gt           0.0839
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0935P)²+1.2795P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1981
_refine_ls_wR_factor_ref         0.2183
_reflns_number_gt                3216
_reflns_number_total             4512
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            rz2727.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2234785
_cod_database_fobs_code          2234785
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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_symmetry_multiplicity
_atom_site_disorder_assembly
_atom_site_disorder_group
N N2 0.32167(9) 0.0538(2) 0.37953(14) 0.0586(6) Uani d . 1 1 . .
H H2A 0.3533 0.0143 0.3918 0.070 Uiso calc R 1 1 . .
C C11 0.36122(12) 0.1175(3) 0.23215(17) 0.0587(7) Uani d . 1 1 . .
C C2 0.49042(11) 0.2243(3) -0.01594(18) 0.0597(7) Uani d . 1 1 . .
C C8 0.44407(11) 0.2199(3) 0.13211(17) 0.0568(7) Uani d . 1 1 . .
N N1 0.42775(12) 0.0475(3) -0.07023(19) 0.0804(8) Uani d . 1 1 . .
C C1 0.48586(12) 0.2708(3) 0.07186(18) 0.0598(7) Uani d . 1 1 . .
C C3 0.52800(13) 0.2724(3) -0.0749(2) 0.0750(9) Uani d . 1 1 . .
H H3A 0.5302 0.2411 -0.1328 0.090 Uiso calc R 1 1 . .
C C15 0.27767(13) -0.0213(3) 0.4206(2) 0.0729(9) Uani d . 1 1 . .
H H15A 0.2431 0.0145 0.4041 0.088 Uiso calc R 1 1 . .
H H15B 0.2787 -0.1056 0.3977 0.088 Uiso calc R 1 1 . .
C C7 0.45498(12) 0.1267(3) -0.04641(19) 0.0624(7) Uani d . 1 1 . .
C C10 0.40494(13) 0.0482(3) 0.21080(19) 0.0679(8) Uani d . 1 1 . .
H H10A 0.4072 -0.0341 0.2296 0.082 Uiso calc R 1 1 . .
C C9 0.44606(13) 0.0986(3) 0.16145(19) 0.0685(8) Uani d . 1 1 . .
H H9A 0.4756 0.0497 0.1478 0.082 Uiso calc R 1 1 . .
C C14 0.31444(13) 0.0585(3) 0.27939(19) 0.0697(8) Uani d . 1 1 . .
H H14A 0.2821 0.1050 0.2649 0.084 Uiso calc R 1 1 . .
H H14B 0.3095 -0.0255 0.2570 0.084 Uiso calc R 1 1 . .
C C12 0.35927(15) 0.2401(3) 0.2056(3) 0.0877(11) Uani d . 1 1 . .
H H12A 0.3301 0.2892 0.2210 0.105 Uiso calc R 1 1 . .
O O1 0.28375(13) 0.0972(4) 0.55657(19) 0.1302(13) Uani d . 1 1 . .
C C13 0.40029(15) 0.2908(3) 0.1561(3) 0.0877(11) Uani d . 1 1 . .
H H13A 0.3984 0.3738 0.1388 0.105 Uiso calc R 1 1 . .
C C6 0.52083(15) 0.3653(3) 0.0969(2) 0.0810(10) Uani d . 1 1 . .
H H6A 0.5191 0.3980 0.1545 0.097 Uiso calc R 1 1 . .
C C4 0.56173(15) 0.3664(3) -0.0467(3) 0.0850(10) Uani d . 1 1 . .
H H4A 0.5869 0.3986 -0.0856 0.102 Uiso calc R 1 1 . .
C C18 0.32429(16) 0.1780(4) 0.4223(3) 0.0940(12) Uani d . 1 1 . .
H H18A 0.2924 0.2252 0.4062 0.113 Uiso calc R 1 1 . .
H H18B 0.3553 0.2229 0.4009 0.113 Uiso calc R 1 1 . .
C C16 0.28390(18) -0.0235(5) 0.5209(2) 0.1058(14) Uani d . 1 1 . .
H H16A 0.2547 -0.0710 0.5462 0.127 Uiso calc R 1 1 . .
H H16B 0.3174 -0.0644 0.5373 0.127 Uiso calc R 1 1 . .
C C5 0.55830(15) 0.4125(4) 0.0386(3) 0.0916(11) Uani d . 1 1 . .
H H5A 0.5813 0.4759 0.0574 0.110 Uiso calc R 1 1 . .
C C17 0.3284(2) 0.1644(5) 0.5233(3) 0.140(2) Uani d . 1 1 . .
H H17A 0.3613 0.1211 0.5394 0.168 Uiso calc R 1 1 . .
H H17B 0.3296 0.2461 0.5507 0.168 Uiso calc R 1 1 . .
P P1 0.15365(4) 0.14226(9) 0.20740(6) 0.0750(3) Uani d . 1 1 . .
F F1 0.1241(5) 0.2534(10) 0.2540(7) 0.141(3) Uani d P 0.65(2) 1 A 1
F F2 0.1364(4) 0.1889(13) 0.1147(8) 0.152(4) Uani d P 0.65(2) 1 A 1
F F3 0.2064(5) 0.2159(11) 0.2041(10) 0.136(4) Uani d P 0.65(2) 1 A 1
F F4 0.0987(4) 0.0652(11) 0.2203(5) 0.113(2) Uani d P 0.65(2) 1 A 1
F F5 0.1803(6) 0.0238(11) 0.1705(8) 0.135(4) Uani d P 0.65(2) 1 A 1
F F6 0.1702(3) 0.0918(8) 0.3061(6) 0.108(2) Uani d P 0.65(2) 1 A 1
F F1' 0.1419(7) 0.2894(14) 0.208(3) 0.161(9) Uani d P 0.35(2) 1 A 2
F F2' 0.1432(9) 0.147(2) 0.1016(11) 0.144(8) Uani d P 0.35(2) 1 A 2
F F3' 0.2163(6) 0.186(2) 0.1825(12) 0.106(5) Uani d P 0.35(2) 1 A 2
F F4' 0.0981(6) 0.116(3) 0.2162(15) 0.168(10) Uani d P 0.35(2) 1 A 2
F F5' 0.1754(15) 0.0133(19) 0.192(2) 0.183(12) Uani d P 0.35(2) 1 A 2
F F6' 0.1687(9) 0.147(4) 0.3025(11) 0.185(10) Uani d P 0.35(2) 1 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
C18 N2 C15 109.6(2)
C18 N2 C14 113.7(3)
C15 N2 C14 110.5(2)
C18 N2 H2A 107.6
C15 N2 H2A 107.6
C14 N2 H2A 107.6
C10 C11 C12 118.7(3)
C10 C11 C14 120.4(3)
C12 C11 C14 120.8(3)
C3 C2 C1 121.4(3)
C3 C2 C7 119.0(3)
C1 C2 C7 119.5(3)
C9 C8 C13 117.6(3)
C9 C8 C1 121.2(3)
C13 C8 C1 121.1(3)
C6 C1 C2 116.7(3)
C6 C1 C8 123.3(3)
C2 C1 C8 120.0(3)
C4 C3 C2 119.5(3)
C4 C3 H3A 120.2
C2 C3 H3A 120.2
C16 C15 N2 110.7(3)
C16 C15 H15A 109.5
N2 C15 H15A 109.5
C16 C15 H15B 109.5
N2 C15 H15B 109.5
H15A C15 H15B 108.1
N1 C7 C2 178.5(3)
C11 C10 C9 120.9(3)
C11 C10 H10A 119.6
C9 C10 H10A 119.6
C8 C9 C10 121.2(3)
C8 C9 H9A 119.4
C10 C9 H9A 119.4
N2 C14 C11 113.5(2)
N2 C14 H14A 108.9
C11 C14 H14A 108.9
N2 C14 H14B 108.9
C11 C14 H14B 108.9
H14A C14 H14B 107.7
C11 C12 C13 120.6(3)
C11 C12 H12A 119.7
C13 C12 H12A 119.7
C16 O1 C17 109.3(3)
C8 C13 C12 120.9(3)
C8 C13 H13A 119.5
C12 C13 H13A 119.5
C5 C6 C1 121.8(3)
C5 C6 H6A 119.1
C1 C6 H6A 119.1
C5 C4 C3 120.1(3)
C5 C4 H4A 119.9
C3 C4 H4A 119.9
N2 C18 C17 110.0(3)
N2 C18 H18A 109.7
C17 C18 H18A 109.7
N2 C18 H18B 109.7
C17 C18 H18B 109.7
H18A C18 H18B 108.2
O1 C16 C15 111.3(3)
O1 C16 H16A 109.4
C15 C16 H16A 109.4
O1 C16 H16B 109.4
C15 C16 H16B 109.4
H16A C16 H16B 108.0
C4 C5 C6 120.4(3)
C4 C5 H5A 119.8
C6 C5 H5A 119.8
O1 C17 C18 111.0(3)
O1 C17 H17A 109.4
C18 C17 H17A 109.4
O1 C17 H17B 109.4
C18 C17 H17B 109.4
H17A C17 H17B 108.0
F4' P1 F6' 98.6(13)
F4' P1 F5' 100.7(18)
F6' P1 F5' 95.1(17)
F4' P1 F2 83.7(11)
F6' P1 F2 158.7(14)
F5' P1 F2 105.3(13)
F4' P1 F3 160.1(12)
F6' P1 F3 79.0(11)
F5' P1 F3 99.2(14)
F2 P1 F3 91.6(6)
F4' P1 F5 107.3(14)
F6' P1 F5 105.6(15)
F2 P1 F5 93.7(7)
F3 P1 F5 92.3(8)
F4' P1 F1 69.1(11)
F6' P1 F1 70.1(14)
F5' P1 F1 159.6(10)
F2 P1 F1 91.4(6)
F3 P1 F1 91.8(5)
F5 P1 F1 173.4(5)
F4' P1 F2' 87.5(11)
F6' P1 F2' 173.3(14)
F5' P1 F2' 86.4(14)
F3 P1 F2' 94.3(8)
F5 P1 F2' 74.8(10)
F1 P1 F2' 110.0(9)
F4' P1 F1' 90.9(12)
F6' P1 F1' 90.5(12)
F5' P1 F1' 166.2(12)
F2 P1 F1' 68.3(10)
F3 P1 F1' 69.4(7)
F5 P1 F1' 153.1(13)
F2' P1 F1' 86.7(11)
F6' P1 F4 96.0(13)
F5' P1 F4 81.5(13)
F2 P1 F4 93.0(6)
F3 P1 F4 175.0(6)
F5 P1 F4 89.4(7)
F1 P1 F4 86.1(6)
F2' P1 F4 90.7(7)
F1' P1 F4 110.5(8)
F4' P1 F6 94.7(11)
F5' P1 F6 74.9(13)
F2 P1 F6 178.3(5)
F3 P1 F6 90.0(5)
F5 P1 F6 86.8(6)
F1 P1 F6 88.0(4)
F2' P1 F6 161.3(9)
F1' P1 F6 111.8(12)
F4 P1 F6 85.4(4)
F4' P1 F3' 170.8(13)
F6' P1 F3' 89.0(11)
F5' P1 F3' 83.6(14)
F2 P1 F3' 87.4(7)
F5 P1 F3' 75.2(9)
F1 P1 F3' 109.2(8)
F2' P1 F3' 84.6(9)
F1' P1 F3' 83.9(9)
F4 P1 F3' 164.7(8)
F6 P1 F3' 94.3(6)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N2 C18 1.482(4)
N2 C15 1.502(4)
N2 C14 1.503(3)
N2 H2A 0.9100
C11 C10 1.362(4)
C11 C12 1.378(4)
C11 C14 1.513(4)
C2 C3 1.396(4)
C2 C1 1.409(4)
C2 C7 1.440(4)
C8 C9 1.377(4)
C8 C13 1.384(4)
C8 C1 1.492(4)
N1 C7 1.142(4)
C1 C6 1.386(4)
C3 C4 1.375(5)
C3 H3A 0.9300
C15 C16 1.502(5)
C15 H15A 0.9700
C15 H15B 0.9700
C10 C9 1.384(4)
C10 H10A 0.9300
C9 H9A 0.9300
C14 H14A 0.9700
C14 H14B 0.9700
C12 C13 1.384(5)
C12 H12A 0.9300
O1 C16 1.403(5)
O1 C17 1.423(5)
C13 H13A 0.9300
C6 C5 1.385(5)
C6 H6A 0.9300
C4 C5 1.370(5)
C4 H4A 0.9300
C18 C17 1.516(5)
C18 H18A 0.9700
C18 H18B 0.9700
C16 H16A 0.9700
C16 H16B 0.9700
C5 H5A 0.9300
C17 H17A 0.9700
C17 H17B 0.9700
P1 F4' 1.421(17)
P1 F6' 1.463(16)
P1 F5' 1.51(2)
P1 F2 1.527(8)
P1 F3 1.536(9)
P1 F5 1.543(9)
P1 F1 1.574(7)
P1 F2' 1.597(15)
P1 F1' 1.610(14)
P1 F4 1.615(9)
P1 F6 1.616(7)
P1 F3' 1.678(17)
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
N2 H2A N1 6_556 0.91 2.04 2.942(4) 170.5
C10 H10A F1 4_545 0.93 2.43 3.296(9) 155.3
C14 H14A F3 . 0.97 2.39 3.355(12) 170.6
C15 H15A F6 . 0.97 2.46 3.377(8) 158.2
C15 H15B F3 4_545 0.97 2.48 3.412(10) 161.0
C15 H15B F3' 4_545 0.97 2.54 3.51(2) 172
C10 H10A F1' 4_545 0.93 2.45 3.26(2) 145
C14 H14B F1' 4_545 0.97 2.38 3.097(16) 130
C5 H5A F2' 3_555 0.93 2.48 3.41(2) 178
C17 H17B F6' 7_556 0.97 2.47 3.29(3) 143
