#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/77/2227714.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_2227714
loop_
_publ_author_name
'Su, Qiu-hong'
'Zang, Hong-Jun'
'Xu, Tian-lin'
'Ren, Yuan-Lin'
_publ_section_title
;
 4-Benzyl-4-methylmorpholinium hexafluorophosphate
;
_journal_coeditor_code           JH2209
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2695
_journal_paper_doi               10.1107/S1600536810038432
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C12 H18 N O +, P F6 -'
_chemical_formula_moiety         'C12 H18 N O +, F6 P -'
_chemical_formula_sum            'C12 H18 F6 N O P'
_chemical_formula_weight         337.24
_chemical_name_systematic
;
4-Benzyl-4-methylmorpholinium hexafluorophosphate
;
_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                104.307(5)
_cell_angle_beta                 96.816(8)
_cell_angle_gamma                95.633(7)
_cell_formula_units_Z            4
_cell_length_a                   9.7268(14)
_cell_length_b                   10.7183(16)
_cell_length_c                   14.537(2)
_cell_measurement_reflns_used    4804
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      27.2
_cell_measurement_theta_min      1.5
_cell_volume                     1445.3(4)
_computing_cell_refinement       'CrystalClear (Rigaku/MSC, 2005)'
_computing_data_collection       'CrystalClear (Rigaku/MSC, 2005)'
_computing_data_reduction        'CrystalClear (Rigaku/MSC, 2005)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXS97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      113(2)
_diffrn_detector_area_resol_mean 14.63
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Rigaku Saturn'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71070
_diffrn_reflns_av_R_equivalents  0.0430
_diffrn_reflns_av_sigmaI/netI    0.0628
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            17415
_diffrn_reflns_theta_full        27.22
_diffrn_reflns_theta_max         27.22
_diffrn_reflns_theta_min         1.46
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.255
_exptl_absorpt_correction_T_max  0.9701
_exptl_absorpt_correction_T_min  0.9461
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrystalClear; Rigaku/MSC, 2005)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.550
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.529
_refine_diff_density_min         -0.403
_refine_ls_extinction_coef       0.0123(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXS97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     401
_refine_ls_number_reflns         6387
_refine_ls_number_restraints     84
_refine_ls_restrained_S_all      1.091
_refine_ls_R_factor_all          0.0676
_refine_ls_R_factor_gt           0.0488
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0518P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1041
_refine_ls_wR_factor_ref         0.1144
_reflns_number_gt                4730
_reflns_number_total             6387
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            jh2209.cif
_cod_data_source_block           I
_cod_database_code               2227714
_cod_database_fobs_code          2227714
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
P P1 0.30855(6) 0.37650(5) 0.09741(4) 0.02340(16) Uani d . 1 . .
P P2 0.78163(6) 0.24754(6) 0.46477(4) 0.02855(17) Uani d D 1 . .
F F1 0.42358(14) 0.39964(13) 0.03267(9) 0.0368(4) Uani d . 1 . .
F F2 0.40636(15) 0.46701(15) 0.19023(9) 0.0463(4) Uani d . 1 . .
F F3 0.23988(14) 0.49934(12) 0.07859(9) 0.0342(3) Uani d . 1 . .
F F4 0.20934(16) 0.28651(14) 0.00513(10) 0.0477(4) Uani d . 1 . .
F F5 0.37474(17) 0.25367(14) 0.11626(10) 0.0485(4) Uani d . 1 . .
F F6 0.19177(15) 0.35492(14) 0.16311(10) 0.0449(4) Uani d . 1 . .
F F7' 0.8866(8) 0.1865(7) 0.5320(5) 0.0485(9) Uani d PD 0.592(6) A 1
F F8' 0.8069(6) 0.1427(5) 0.3741(3) 0.0583(12) Uani d PDU 0.592(6) A 1
F F9' 0.6552(6) 0.1530(5) 0.4805(4) 0.0444(11) Uani d PDU 0.592(6) A 1
F F10' 0.7621(6) 0.3542(5) 0.5615(4) 0.0595(14) Uani d PDU 0.592(6) A 1
F F11' 0.9139(4) 0.3438(5) 0.4548(4) 0.0648(13) Uani d PDU 0.592(6) A 1
F F12' 0.6806(7) 0.3126(7) 0.4031(6) 0.0322(4) Uani d PD 0.592(6) A 1
F F7 0.8809(11) 0.1709(11) 0.5169(8) 0.0485(9) Uani d PD 0.408(6) A 2
F F8 0.7411(7) 0.1201(7) 0.3742(5) 0.0583(12) Uani d PDU 0.408(6) A 2
F F9 0.6530(9) 0.1932(7) 0.5062(6) 0.0444(11) Uani d PDU 0.408(6) A 2
F F10 0.8134(9) 0.3697(7) 0.5478(6) 0.0595(14) Uani d PDU 0.408(6) A 2
F F11 0.9009(7) 0.2907(8) 0.4109(5) 0.0648(13) Uani d PDU 0.408(6) A 2
F F12 0.6762(11) 0.3186(11) 0.4054(8) 0.0322(4) Uani d PD 0.408(6) A 2
O O1 1.00560(16) 0.81093(14) 0.22635(11) 0.0328(4) Uani d . 1 . .
O O2 0.27675(18) 0.27512(15) 0.54849(10) 0.0333(4) Uani d . 1 . .
N N1 0.85004(17) 0.55784(16) 0.20963(12) 0.0205(4) Uani d . 1 . .
N N2 0.23494(18) 0.16209(16) 0.34181(12) 0.0215(4) Uani d . 1 . .
C C1 0.9767(2) 0.5774(2) 0.16140(15) 0.0235(5) Uani d . 1 . .
H H1A 0.9459 0.5845 0.0957 0.028 Uiso calc R 1 . .
H H1B 1.0272 0.5007 0.1559 0.028 Uiso calc R 1 . .
C C2 1.0748(2) 0.6979(2) 0.21631(17) 0.0295(5) Uani d . 1 . .
H H2A 1.1104 0.6888 0.2807 0.035 Uiso calc R 1 . .
H H2B 1.1556 0.7076 0.1820 0.035 Uiso calc R 1 . .
C C3 0.8918(2) 0.8002(2) 0.27847(16) 0.0304(5) Uani d . 1 . .
H H3A 0.8457 0.8797 0.2861 0.037 Uiso calc R 1 . .
H H3B 0.9276 0.7928 0.3433 0.037 Uiso calc R 1 . .
C C4 0.7860(2) 0.6831(2) 0.22778(16) 0.0262(5) Uani d . 1 . .
H H4A 0.7435 0.6950 0.1657 0.031 Uiso calc R 1 . .
H H4B 0.7107 0.6769 0.2673 0.031 Uiso calc R 1 . .
C C5 0.7400(2) 0.4531(2) 0.14237(15) 0.0234(5) Uani d . 1 . .
H H5A 0.6536 0.4513 0.1721 0.028 Uiso calc R 1 . .
H H5B 0.7180 0.4783 0.0817 0.028 Uiso calc R 1 . .
C C6 0.7801(2) 0.3181(2) 0.11851(15) 0.0237(5) Uani d . 1 . .
C C7 0.7297(2) 0.2279(2) 0.16439(17) 0.0317(5) Uani d . 1 . .
H H7 0.6761 0.2540 0.2147 0.038 Uiso calc R 1 . .
C C8 0.7564(3) 0.1000(2) 0.13772(19) 0.0406(6) Uani d . 1 . .
H H8 0.7215 0.0391 0.1697 0.049 Uiso calc R 1 . .
C C9 0.8342(3) 0.0617(2) 0.0645(2) 0.0433(7) Uani d . 1 . .
H H9 0.8526 -0.0257 0.0457 0.052 Uiso calc R 1 . .
C C10 0.8852(3) 0.1513(3) 0.01851(19) 0.0415(7) Uani d . 1 . .
H H10 0.9394 0.1252 -0.0314 0.050 Uiso calc R 1 . .
C C11 0.8581(2) 0.2777(2) 0.04457(16) 0.0314(6) Uani d . 1 . .
H H11 0.8927 0.3380 0.0120 0.038 Uiso calc R 1 . .
C C12 0.8884(2) 0.5197(2) 0.30086(14) 0.0262(5) Uani d . 1 . .
H H12A 0.9362 0.4423 0.2874 0.039 Uiso calc R 1 . .
H H12B 0.8035 0.5008 0.3279 0.039 Uiso calc R 1 . .
H H12C 0.9505 0.5912 0.3470 0.039 Uiso calc R 1 . .
C C13 0.2326(2) 0.3049(2) 0.38787(16) 0.0275(5) Uani d . 1 . .
H H13A 0.1351 0.3204 0.3943 0.033 Uiso calc R 1 . .
H H13B 0.2675 0.3568 0.3457 0.033 Uiso calc R 1 . .
C C14 0.3215(3) 0.3497(2) 0.48603(16) 0.0321(6) Uani d . 1 . .
H H14A 0.4204 0.3410 0.4792 0.038 Uiso calc R 1 . .
H H14B 0.3151 0.4426 0.5144 0.038 Uiso calc R 1 . .
C C15 0.2877(3) 0.1415(2) 0.50940(15) 0.0297(5) Uani d . 1 . .
H H15A 0.2595 0.0912 0.5543 0.036 Uiso calc R 1 . .
H H15B 0.3861 0.1314 0.5018 0.036 Uiso calc R 1 . .
C C16 0.1962(2) 0.0883(2) 0.41301(15) 0.0245(5) Uani d . 1 . .
H H16A 0.2060 -0.0045 0.3877 0.029 Uiso calc R 1 . .
H H16B 0.0972 0.0943 0.4212 0.029 Uiso calc R 1 . .
C C17 0.3792(2) 0.1439(2) 0.31398(15) 0.0233(5) Uani d . 1 . .
H H17A 0.4005 0.2021 0.2728 0.028 Uiso calc R 1 . .
H H17B 0.4486 0.1724 0.3731 0.028 Uiso calc R 1 . .
C C18 0.3991(2) 0.0077(2) 0.26190(15) 0.0222(5) Uani d . 1 . .
C C19 0.4247(2) -0.0859(2) 0.31083(15) 0.0259(5) Uani d . 1 . .
H H19 0.4245 -0.0661 0.3782 0.031 Uiso calc R 1 . .
C C20 0.4506(2) -0.2080(2) 0.26217(16) 0.0305(5) Uani d . 1 . .
H H20 0.4643 -0.2723 0.2959 0.037 Uiso calc R 1 . .
C C21 0.4564(2) -0.2362(2) 0.16470(16) 0.0281(5) Uani d . 1 . .
H H21 0.4756 -0.3193 0.1316 0.034 Uiso calc R 1 . .
C C22 0.4341(2) -0.1434(2) 0.11574(16) 0.0294(5) Uani d . 1 . .
H H22 0.4394 -0.1622 0.0490 0.035 Uiso calc R 1 . .
C C23 0.4040(2) -0.0223(2) 0.16372(15) 0.0278(5) Uani d . 1 . .
H H23 0.3866 0.0405 0.1292 0.033 Uiso calc R 1 . .
C C24 0.1262(2) 0.1182(2) 0.25385(15) 0.0289(5) Uani d . 1 . .
H H24A 0.1221 0.0244 0.2269 0.043 Uiso calc R 1 . .
H H24B 0.1508 0.1637 0.2061 0.043 Uiso calc R 1 . .
H H24C 0.0350 0.1380 0.2712 0.043 Uiso calc R 1 . .
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
F1 P1 F5 . . 90.51(8) ?
F1 P1 F4 . . 89.97(8) ?
F5 P1 F4 . . 90.45(9) ?
F1 P1 F2 . . 90.56(8) ?
F5 P1 F2 . . 89.86(9) ?
F4 P1 F2 . . 179.38(8) ?
F1 P1 F3 . . 90.16(7) ?
F5 P1 F3 . . 179.23(8) ?
F4 P1 F3 . . 89.18(8) ?
F2 P1 F3 . . 90.50(8) ?
F1 P1 F6 . . 179.29(8) ?
F5 P1 F6 . . 90.15(8) ?
F4 P1 F6 . . 90.26(8) ?
F2 P1 F6 . . 89.20(8) ?
F3 P1 F6 . . 89.18(7) ?
F10 P2 F8' . . 157.7(3) ?
F10 P2 F11 . . 94.0(3) ?
F8' P2 F11 . . 64.7(3) ?
F10 P2 F7 . . 93.1(4) ?
F8' P2 F7 . . 81.6(5) ?
F11 P2 F7 . . 91.5(4) ?
F10 P2 F9 . . 92.6(3) ?
F8' P2 F9 . . 109.1(3) ?
F11 P2 F9 . . 172.8(4) ?
F7 P2 F9 . . 91.0(4) ?
F10 P2 F12' . . 92.7(6) ?
F8' P2 F12' . . 92.7(3) ?
F11 P2 F12' . . 87.2(5) ?
F7 P2 F12' . . 174.2(6) ?
F9 P2 F12' . . 89.6(6) ?
F10 P2 F9' . . 110.4(3) ?
F8' P2 F9' . . 91.0(2) ?
F11 P2 F9' . . 155.6(3) ?
F7 P2 F9' . . 86.9(6) ?
F9 P2 F9' . . 18.2(3) ?
F12' P2 F9' . . 91.9(3) ?
F10 P2 F11' . . 67.6(3) ?
F8' P2 F11' . . 90.77(19) ?
F11 P2 F11' . . 26.5(3) ?
F7 P2 F11' . . 90.7(5) ?
F9 P2 F11' . . 160.1(3) ?
F12' P2 F11' . . 90.7(3) ?
F9' P2 F11' . . 176.8(3) ?
F10 P2 F10' . . 21.1(4) ?
F8' P2 F10' . . 177.2(3) ?
F11 P2 F10' . . 114.7(3) ?
F7 P2 F10' . . 95.7(6) ?
F9 P2 F10' . . 71.7(3) ?
F12' P2 F10' . . 90.0(3) ?
F9' P2 F10' . . 89.7(2) ?
F11' P2 F10' . . 88.5(2) ?
F10 P2 F7' . . 84.8(6) ?
F8' P2 F7' . . 89.7(3) ?
F11 P2 F7' . . 93.0(5) ?
F7 P2 F7' . . 8.3(7) ?
F9 P2 F7' . . 90.4(6) ?
F12' P2 F7' . . 177.5(4) ?
F9' P2 F7' . . 88.9(3) ?
F11' P2 F7' . . 88.4(3) ?
F10' P2 F7' . . 87.6(3) ?
F10 P2 F8 . . 177.2(4) ?
F8' P2 F8 . . 23.8(2) ?
F11 P2 F8 . . 86.7(3) ?
F7 P2 F8 . . 89.6(4) ?
F9 P2 F8 . . 86.6(3) ?
F12' P2 F8 . . 84.6(5) ?
F9' P2 F8 . . 68.9(3) ?
F11' P2 F8 . . 113.2(2) ?
F10' P2 F8 . . 157.7(2) ?
F7' P2 F8 . . 97.9(5) ?
F10 P2 F12 . . 90.5(4) ?
F8' P2 F12 . . 95.1(5) ?
F11 P2 F12 . . 88.5(4) ?
F7 P2 F12 . . 176.4(5) ?
F9 P2 F12 . . 88.6(4) ?
F12' P2 F12 . . 2.4(7) ?
F9' P2 F12 . . 91.7(6) ?
F11' P2 F12 . . 90.9(5) ?
F10' P2 F12 . . 87.6(6) ?
F7' P2 F12 . . 175.2(6) ?
F8 P2 F12 . . 86.8(4) ?
C3 O1 C2 . . 110.05(17) ?
C15 O2 C14 . . 110.09(15) ?
C12 N1 C1 . . 111.17(16) ?
C12 N1 C4 . . 111.53(16) ?
C1 N1 C4 . . 107.61(16) ?
C12 N1 C5 . . 109.33(16) ?
C1 N1 C5 . . 110.28(15) ?
C4 N1 C5 . . 106.81(16) ?
C24 N2 C16 . . 108.23(17) ?
C24 N2 C13 . . 109.28(16) ?
C16 N2 C13 . . 107.35(15) ?
C24 N2 C17 . . 109.83(16) ?
C16 N2 C17 . . 113.36(16) ?
C13 N2 C17 . . 108.70(16) ?
N1 C1 C2 . . 112.04(16) ?
N1 C1 H1A . . 109.2 ?
C2 C1 H1A . . 109.2 ?
N1 C1 H1B . . 109.2 ?
C2 C1 H1B . . 109.2 ?
H1A C1 H1B . . 107.9 ?
O1 C2 C1 . . 110.99(18) ?
O1 C2 H2A . . 109.4 ?
C1 C2 H2A . . 109.4 ?
O1 C2 H2B . . 109.4 ?
C1 C2 H2B . . 109.4 ?
H2A C2 H2B . . 108.0 ?
O1 C3 C4 . . 111.43(17) ?
O1 C3 H3A . . 109.3 ?
C4 C3 H3A . . 109.3 ?
O1 C3 H3B . . 109.3 ?
C4 C3 H3B . . 109.3 ?
H3A C3 H3B . . 108.0 ?
C3 C4 N1 . . 112.51(18) ?
C3 C4 H4A . . 109.1 ?
N1 C4 H4A . . 109.1 ?
C3 C4 H4B . . 109.1 ?
N1 C4 H4B . . 109.1 ?
H4A C4 H4B . . 107.8 ?
C6 C5 N1 . . 115.64(17) ?
C6 C5 H5A . . 108.4 ?
N1 C5 H5A . . 108.4 ?
C6 C5 H5B . . 108.4 ?
N1 C5 H5B . . 108.4 ?
H5A C5 H5B . . 107.4 ?
C7 C6 C11 . . 118.6(2) ?
C7 C6 C5 . . 120.2(2) ?
C11 C6 C5 . . 120.9(2) ?
C6 C7 C8 . . 120.9(2) ?
C6 C7 H7 . . 119.6 ?
C8 C7 H7 . . 119.6 ?
C9 C8 C7 . . 119.7(3) ?
C9 C8 H8 . . 120.1 ?
C7 C8 H8 . . 120.1 ?
C8 C9 C10 . . 119.7(2) ?
C8 C9 H9 . . 120.1 ?
C10 C9 H9 . . 120.1 ?
C11 C10 C9 . . 120.5(2) ?
C11 C10 H10 . . 119.7 ?
C9 C10 H10 . . 119.7 ?
C10 C11 C6 . . 120.5(2) ?
C10 C11 H11 . . 119.7 ?
C6 C11 H11 . . 119.7 ?
N1 C12 H12A . . 109.5 ?
N1 C12 H12B . . 109.5 ?
H12A C12 H12B . . 109.5 ?
N1 C12 H12C . . 109.5 ?
H12A C12 H12C . . 109.5 ?
H12B C12 H12C . . 109.5 ?
N2 C13 C14 . . 111.92(17) ?
N2 C13 H13A . . 109.2 ?
C14 C13 H13A . . 109.2 ?
N2 C13 H13B . . 109.2 ?
C14 C13 H13B . . 109.2 ?
H13A C13 H13B . . 107.9 ?
O2 C14 C13 . . 111.06(19) ?
O2 C14 H14A . . 109.4 ?
C13 C14 H14A . . 109.4 ?
O2 C14 H14B . . 109.4 ?
C13 C14 H14B . . 109.4 ?
H14A C14 H14B . . 108.0 ?
O2 C15 C16 . . 111.24(17) ?
O2 C15 H15A . . 109.4 ?
C16 C15 H15A . . 109.4 ?
O2 C15 H15B . . 109.4 ?
C16 C15 H15B . . 109.4 ?
H15A C15 H15B . . 108.0 ?
N2 C16 C15 . . 111.46(18) ?
N2 C16 H16A . . 109.3 ?
C15 C16 H16A . . 109.3 ?
N2 C16 H16B . . 109.3 ?
C15 C16 H16B . . 109.3 ?
H16A C16 H16B . . 108.0 ?
C18 C17 N2 . . 116.30(17) ?
C18 C17 H17A . . 108.2 ?
N2 C17 H17A . . 108.2 ?
C18 C17 H17B . . 108.2 ?
N2 C17 H17B . . 108.2 ?
H17A C17 H17B . . 107.4 ?
C19 C18 C23 . . 118.67(19) ?
C19 C18 C17 . . 121.67(19) ?
C23 C18 C17 . . 119.42(19) ?
C20 C19 C18 . . 120.6(2) ?
C20 C19 H19 . . 119.7 ?
C18 C19 H19 . . 119.7 ?
C21 C20 C19 . . 120.1(2) ?
C21 C20 H20 . . 119.9 ?
C19 C20 H20 . . 119.9 ?
C22 C21 C20 . . 119.8(2) ?
C22 C21 H21 . . 120.1 ?
C20 C21 H21 . . 120.1 ?
C21 C22 C23 . . 120.2(2) ?
C21 C22 H22 . . 119.9 ?
C23 C22 H22 . . 119.9 ?
C22 C23 C18 . . 120.5(2) ?
C22 C23 H23 . . 119.8 ?
C18 C23 H23 . . 119.8 ?
N2 C24 H24A . . 109.5 ?
N2 C24 H24B . . 109.5 ?
H24A C24 H24B . . 109.5 ?
N2 C24 H24C . . 109.5 ?
H24A C24 H24C . . 109.5 ?
H24B C24 H24C . . 109.5 ?
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
P1 F1 . 1.5843(13) ?
P1 F5 . 1.5893(13) ?
P1 F4 . 1.5910(14) ?
P1 F2 . 1.5919(14) ?
P1 F3 . 1.6005(13) ?
P1 F6 . 1.6035(14) ?
P2 F10 . 1.523(6) ?
P2 F8' . 1.568(4) ?
P2 F11 . 1.569(5) ?
P2 F7 . 1.572(6) ?
P2 F9 . 1.573(6) ?
P2 F12' . 1.578(5) ?
P2 F9' . 1.590(4) ?
P2 F11' . 1.612(4) ?
P2 F10' . 1.623(4) ?
P2 F7' . 1.624(4) ?
P2 F8 . 1.624(6) ?
P2 F12 . 1.626(6) ?
O1 C3 . 1.425(3) ?
O1 C2 . 1.427(3) ?
O2 C15 . 1.424(2) ?
O2 C14 . 1.427(3) ?
N1 C12 . 1.498(3) ?
N1 C1 . 1.510(2) ?
N1 C4 . 1.513(3) ?
N1 C5 . 1.528(3) ?
N2 C24 . 1.503(3) ?
N2 C16 . 1.509(3) ?
N2 C13 . 1.515(3) ?
N2 C17 . 1.524(3) ?
C1 C2 . 1.512(3) ?
C1 H1A . 0.9900 ?
C1 H1B . 0.9900 ?
C2 H2A . 0.9900 ?
C2 H2B . 0.9900 ?
C3 C4 . 1.512(3) ?
C3 H3A . 0.9900 ?
C3 H3B . 0.9900 ?
C4 H4A . 0.9900 ?
C4 H4B . 0.9900 ?
C5 C6 . 1.503(3) ?
C5 H5A . 0.9900 ?
C5 H5B . 0.9900 ?
C6 C7 . 1.386(3) ?
C6 C11 . 1.395(3) ?
C7 C8 . 1.389(3) ?
C7 H7 . 0.9500 ?
C8 C9 . 1.382(4) ?
C8 H8 . 0.9500 ?
C9 C10 . 1.384(4) ?
C9 H9 . 0.9500 ?
C10 C11 . 1.374(3) ?
C10 H10 . 0.9500 ?
C11 H11 . 0.9500 ?
C12 H12A . 0.9800 ?
C12 H12B . 0.9800 ?
C12 H12C . 0.9800 ?
C13 C14 . 1.517(3) ?
C13 H13A . 0.9900 ?
C13 H13B . 0.9900 ?
C14 H14A . 0.9900 ?
C14 H14B . 0.9900 ?
C15 C16 . 1.513(3) ?
C15 H15A . 0.9900 ?
C15 H15B . 0.9900 ?
C16 H16A . 0.9900 ?
C16 H16B . 0.9900 ?
C17 C18 . 1.512(3) ?
C17 H17A . 0.9900 ?
C17 H17B . 0.9900 ?
C18 C19 . 1.391(3) ?
C18 C23 . 1.391(3) ?
C19 C20 . 1.387(3) ?
C19 H19 . 0.9500 ?
C20 C21 . 1.383(3) ?
C20 H20 . 0.9500 ?
C21 C22 . 1.377(3) ?
C21 H21 . 0.9500 ?
C22 C23 . 1.391(3) ?
C22 H22 . 0.9500 ?
C23 H23 . 0.9500 ?
C24 H24A . 0.9800 ?
C24 H24B . 0.9800 ?
C24 H24C . 0.9800 ?
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
C12 N1 C1 C2 . . . . -70.4(2) ?
C4 N1 C1 C2 . . . . 52.0(2) ?
C5 N1 C1 C2 . . . . 168.14(17) ?
C3 O1 C2 C1 . . . . 61.1(2) ?
N1 C1 C2 O1 . . . . -58.5(2) ?
C2 O1 C3 C4 . . . . -60.1(2) ?
O1 C3 C4 N1 . . . . 56.6(2) ?
C12 N1 C4 C3 . . . . 71.1(2) ?
C1 N1 C4 C3 . . . . -51.1(2) ?
C5 N1 C4 C3 . . . . -169.51(17) ?
C12 N1 C5 C6 . . . . -56.4(2) ?
C1 N1 C5 C6 . . . . 66.1(2) ?
C4 N1 C5 C6 . . . . -177.22(17) ?
N1 C5 C6 C7 . . . . 101.2(2) ?
N1 C5 C6 C11 . . . . -84.4(2) ?
C11 C6 C7 C8 . . . . 0.2(3) ?
C5 C6 C7 C8 . . . . 174.8(2) ?
C6 C7 C8 C9 . . . . 0.0(4) ?
C7 C8 C9 C10 . . . . 0.2(4) ?
C8 C9 C10 C11 . . . . -0.6(4) ?
C9 C10 C11 C6 . . . . 0.8(4) ?
C7 C6 C11 C10 . . . . -0.6(3) ?
C5 C6 C11 C10 . . . . -175.1(2) ?
C24 N2 C13 C14 . . . . 170.01(18) ?
C16 N2 C13 C14 . . . . 52.8(2) ?
C17 N2 C13 C14 . . . . -70.1(2) ?
C15 O2 C14 C13 . . . . 60.1(2) ?
N2 C13 C14 O2 . . . . -57.5(2) ?
C14 O2 C15 C16 . . . . -61.0(2) ?
C24 N2 C16 C15 . . . . -171.17(16) ?
C13 N2 C16 C15 . . . . -53.3(2) ?
C17 N2 C16 C15 . . . . 66.7(2) ?
O2 C15 C16 N2 . . . . 59.0(2) ?
C24 N2 C17 C18 . . . . -57.3(2) ?
C16 N2 C17 C18 . . . . 63.9(2) ?
C13 N2 C17 C18 . . . . -176.85(17) ?
N2 C17 C18 C19 . . . . -80.6(2) ?
N2 C17 C18 C23 . . . . 105.1(2) ?
C23 C18 C19 C20 . . . . -1.9(3) ?
C17 C18 C19 C20 . . . . -176.3(2) ?
C18 C19 C20 C21 . . . . 2.5(3) ?
C19 C20 C21 C22 . . . . -1.1(3) ?
C20 C21 C22 C23 . . . . -0.9(3) ?
C21 C22 C23 C18 . . . . 1.5(3) ?
C19 C18 C23 C22 . . . . -0.1(3) ?
C17 C18 C23 C22 . . . . 174.43(19) ?
