# Supplementary Material (ESI) for Chemical Communications
# This journal is (c) The Royal Society of Chemistry 2008

data_global
_journal_name_full               Chem.Commun.

_journal_coden_Cambridge         0182
_journal_volume                  ?
_journal_page_first              ?
_journal_year                    ?

_publ_contact_author_name        'ProfD Ji-Chang Xiao'
_publ_contact_author_email       JCHXIAO@MAIL.SIOC.AC.CN

_publ_section_title              
;
Novel Low Melting Salts with Donor-Acceptor
Substituents as Targets for Second-Order Nonlinear Optical Applications
;
loop_
_publ_author_name
'Ji-Chang Xiao.'
'Qing-Yun Chen.'
'Chaosen Chen.'
'Yi-Ping Cui.'
;
Shaoji Xiang
;
'Zhuo Zeng.'
'Zhi-Qiang Zhu.'

# Attachment 'cd263431.cif'

data_cd26343
_database_code_depnum_ccdc_archive 'CCDC 682525'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H13 F6 N4 O5 P'
_chemical_formula_weight         486.27

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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'

_cell_length_a                   11.1474(10)
_cell_length_b                   16.3515(15)
_cell_length_c                   12.3412(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 115.839(2)
_cell_angle_gamma                90.00
_cell_volume                     2024.6(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2732
_cell_measurement_theta_min      4.433
_cell_measurement_theta_max      42.932

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.497
_exptl_crystal_size_mid          0.419
_exptl_crystal_size_min          0.321
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.595
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             984
_exptl_absorpt_coefficient_mu    0.228
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.76071
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11841
_diffrn_reflns_av_R_equivalents  0.0977
_diffrn_reflns_av_sigmaI/netI    0.0687
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.03
_diffrn_reflns_theta_max         27.00
_reflns_number_total             4395
_reflns_number_gt                2694
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.1466P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.003(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_number_reflns         4395
_refine_ls_number_parameters     291
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1069
_refine_ls_R_factor_gt           0.0755
_refine_ls_wR_factor_ref         0.2522
_refine_ls_wR_factor_gt          0.2264
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.043
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.39505(10) 0.08707(5) 0.15552(9) 0.0596(4) Uani 1 1 d . . .
O1 O 1.1578(3) 0.00684(19) 0.4486(3) 0.0827(9) Uani 1 1 d . . .
O2 O 0.5665(4) 0.29170(18) 0.0299(3) 0.0946(10) Uani 1 1 d . . .
O3 O 0.3854(4) 0.3414(2) 0.0136(3) 0.1119(12) Uani 1 1 d . . .
O4 O -0.0352(5) 0.2163(3) -0.2354(6) 0.118(2) Uani 1 1 d . . .
O5 O -0.0516(4) 0.1767(3) -0.4093(6) 0.116(2) Uani 1 1 d . . .
N1 N 0.5699(3) 0.16790(17) -0.1078(2) 0.0559(7) Uani 1 1 d . . .
N2 N 0.7663(3) 0.13207(17) 0.0235(2) 0.0564(7) Uani 1 1 d . . .
N3 N 0.4475(4) 0.29397(18) -0.0157(3) 0.0726(9) Uani 1 1 d . . .
N4 N 0.0107(5) 0.1954(3) -0.3032(7) 0.1116(17) Uani 1 1 d . . .
F1 F 0.2620(4) 0.1317(3) 0.1136(4) 0.1223(18) Uani 1 1 d . . .
F2 F 0.5330(4) 0.0448(2) 0.1939(4) 0.1229(17) Uani 1 1 d . . .
F3 F 0.4611(4) 0.17056(17) 0.1449(3) 0.1215(11) Uani 1 1 d . . .
F4 F 0.3324(4) 0.00348(17) 0.1634(4) 0.1409(14) Uani 1 1 d . . .
F5 F 0.3706(4) 0.0691(2) 0.0212(3) 0.1255(12) Uani 1 1 d . . .
F6 F 0.4175(4) 0.10748(19) 0.2853(3) 0.1409(15) Uani 1 1 d . . .
C1 C 0.6375(3) 0.1285(2) -0.0051(3) 0.0547(8) Uani 1 1 d . . .
H1 H 0.6001 0.1024 0.0398 0.066 Uiso 1 1 calc R . .
C2 C 0.7804(4) 0.1746(3) -0.0672(4) 0.0764(11) Uani 1 1 d . . .
H2 H 0.8605 0.1859 -0.0707 0.092 Uiso 1 1 calc R . .
C3 C 0.6593(4) 0.1968(3) -0.1488(4) 0.0736(11) Uani 1 1 d . . .
H3 H 0.6390 0.2259 -0.2194 0.088 Uiso 1 1 calc R . .
C4 C 0.4299(3) 0.18064(19) -0.1601(3) 0.0534(8) Uani 1 1 d . . .
C5 C 0.3516(4) 0.1323(2) -0.2568(3) 0.0641(9) Uani 1 1 d . . .
H5 H 0.3913 0.0959 -0.2892 0.077 Uiso 1 1 calc R . .
C6 C 0.2138(4) 0.1380(2) -0.3060(4) 0.0763(11) Uani 1 1 d . . .
H6 H 0.1598 0.1064 -0.3719 0.092 Uiso 1 1 calc R . .
C7 C 0.1605(4) 0.1909(2) -0.2549(4) 0.0747(11) Uani 1 1 d . . .
C8 C 0.2320(4) 0.2407(2) -0.1620(4) 0.0702(10) Uani 1 1 d . . .
H8 H 0.1902 0.2767 -0.1310 0.084 Uiso 1 1 calc R . .
C9 C 0.3704(4) 0.23655(19) -0.1140(3) 0.0595(9) Uani 1 1 d . . .
C10 C 0.8690(3) 0.0988(2) 0.1313(3) 0.0565(8) Uani 1 1 d . . .
C11 C 0.9828(4) 0.0657(3) 0.1305(4) 0.0734(11) Uani 1 1 d . . .
H11 H 0.9929 0.0641 0.0596 0.088 Uiso 1 1 calc R . .
C12 C 1.0815(4) 0.0348(3) 0.2364(4) 0.0783(12) Uani 1 1 d . . .
H12 H 1.1591 0.0137 0.2366 0.094 Uiso 1 1 calc R . .
C13 C 1.0666(4) 0.0349(2) 0.3404(4) 0.0647(9) Uani 1 1 d . . .
C14 C 0.9500(4) 0.0670(3) 0.3400(3) 0.0706(10) Uani 1 1 d . . .
H14 H 0.9382 0.0663 0.4101 0.085 Uiso 1 1 calc R . .
C15 C 0.8533(4) 0.0993(2) 0.2364(3) 0.0640(9) Uani 1 1 d . . .
H15 H 0.7768 0.1217 0.2367 0.077 Uiso 1 1 calc R . .
C16 C 1.2767(4) -0.0321(3) 0.4533(5) 0.0987(15) Uani 1 1 d . . .
H16A H 1.2518 -0.0763 0.3966 0.128 Uiso 1 1 calc R . .
H16B H 1.3290 -0.0528 0.5329 0.128 Uiso 1 1 calc R . .
H16C H 1.3281 0.0072 0.4335 0.128 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
P1 0.0813(7) 0.0470(5) 0.0645(6) -0.0018(4) 0.0447(5) -0.0012(4)
O1 0.0670(16) 0.094(2) 0.083(2) 0.0186(16) 0.0288(14) 0.0198(14)
O2 0.109(2) 0.0719(19) 0.086(2) -0.0277(16) 0.0265(19) -0.0198(17)
O3 0.128(3) 0.088(2) 0.100(3) -0.0269(19) 0.077(2) 0.010(2)
O4 0.109(3) 0.107(4) 0.156(7) 0.004(4) 0.096(4) 0.020(3)
O5 0.092(3) 0.130(4) 0.141(5) 0.003(3) -0.001(3) -0.001(2)
N1 0.0717(18) 0.0494(14) 0.0503(16) 0.0007(12) 0.0300(13) -0.0070(12)
N2 0.0650(17) 0.0566(15) 0.0522(16) -0.0027(12) 0.0298(13) -0.0075(13)
N3 0.118(3) 0.0482(17) 0.058(2) -0.0019(14) 0.045(2) -0.0041(18)
N4 0.084(3) 0.073(3) 0.157(5) 0.019(3) 0.034(3) 0.000(2)
F1 0.126(3) 0.143(4) 0.166(5) 0.049(3) 0.093(3) 0.055(3)
F2 0.137(3) 0.138(3) 0.154(5) 0.077(3) 0.111(3) 0.063(2)
F3 0.186(3) 0.0739(17) 0.126(2) -0.0080(16) 0.088(2) -0.0368(18)
F4 0.144(4) 0.0732(18) 0.129(3) -0.0369(19) 0.184(3) -0.051(2)
F5 0.198(3) 0.115(2) 0.089(2) -0.0274(17) 0.086(2) -0.052(2)
F6 0.174(5) 0.089(2) 0.090(2) -0.0164(16) 0.108(3) -0.016(2)
C1 0.069(2) 0.0510(18) 0.0509(19) 0.0028(14) 0.0322(16) -0.0039(15)
C2 0.082(3) 0.092(3) 0.067(3) 0.009(2) 0.044(2) -0.018(2)
C3 0.085(3) 0.084(3) 0.056(2) 0.0160(19) 0.034(2) -0.013(2)
C4 0.073(2) 0.0418(15) 0.0465(18) 0.0069(13) 0.0265(16) -0.0004(14)
C5 0.086(3) 0.0488(18) 0.052(2) -0.0010(15) 0.0244(18) 0.0051(17)
C6 0.083(3) 0.054(2) 0.069(3) 0.0026(18) 0.011(2) -0.0042(19)
C7 0.070(2) 0.053(2) 0.091(3) 0.018(2) 0.026(2) 0.0045(17)
C8 0.085(3) 0.0478(19) 0.083(3) 0.0155(18) 0.042(2) 0.0121(17)
C9 0.088(2) 0.0404(16) 0.0537(19) 0.0067(14) 0.0343(18) -0.0018(15)
C10 0.0580(19) 0.0579(19) 0.056(2) -0.0047(15) 0.0269(16) -0.0052(14)
C11 0.074(2) 0.094(3) 0.063(2) -0.003(2) 0.040(2) 0.003(2)
C12 0.063(2) 0.095(3) 0.087(3) -0.002(2) 0.043(2) 0.010(2)
C13 0.061(2) 0.064(2) 0.070(2) 0.0104(18) 0.0288(18) 0.0034(16)
C14 0.069(2) 0.087(3) 0.063(2) 0.010(2) 0.0354(19) 0.008(2)
C15 0.065(2) 0.074(2) 0.062(2) 0.0077(18) 0.0358(18) 0.0068(17)
C16 0.070(3) 0.110(4) 0.107(4) 0.020(3) 0.030(2) 0.019(3)

_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

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 F1 1.527(4) . ?
P1 F6 1.546(3) . ?
P1 F4 1.557(3) . ?
P1 F2 1.559(3) . ?
P1 F3 1.584(3) . ?
P1 F5 1.585(3) . ?
O1 C13 1.358(5) . ?
O1 C16 1.449(5) . ?
O2 N3 1.195(4) . ?
O3 N3 1.195(5) . ?
O4 N4 1.205(7) . ?
O5 N4 1.224(7) . ?
N1 C1 1.325(4) . ?
N1 C3 1.382(5) . ?
N1 C4 1.421(4) . ?
N2 C1 1.322(4) . ?
N2 C2 1.384(4) . ?
N2 C10 1.432(4) . ?
N3 C9 1.477(5) . ?
N4 C7 1.510(6) . ?
F2 H1 2.5109 . ?
C1 H1 0.9300 . ?
C2 C3 1.336(6) . ?
C2 H2 0.9300 . ?
C3 H3 0.9300 . ?
C4 C5 1.379(5) . ?
C4 C9 1.389(5) . ?
C5 C6 1.388(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.351(6) . ?
C6 H6 0.9300 . ?
C7 C8 1.348(6) . ?
C8 C9 1.392(5) . ?
C8 H8 0.9300 . ?
C10 C15 1.381(5) . ?
C10 C11 1.383(5) . ?
C11 C12 1.385(5) . ?
C11 H11 0.9300 . ?
C12 C13 1.364(5) . ?
C12 H12 0.9300 . ?
C13 C14 1.399(5) . ?
C14 C15 1.370(5) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?

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
F1 P1 F6 86.7(2) . . ?
F1 P1 F4 92.6(2) . . ?
F6 P1 F4 89.97(18) . . ?
F1 P1 F2 176.8(2) . . ?
F6 P1 F2 95.0(2) . . ?
F4 P1 F2 90.1(2) . . ?
F1 P1 F3 88.8(2) . . ?
F6 P1 F3 91.63(18) . . ?
F4 P1 F3 177.98(17) . . ?
F2 P1 F3 88.5(2) . . ?
F1 P1 F5 92.0(2) . . ?
F6 P1 F5 178.13(19) . . ?
F4 P1 F5 91.43(17) . . ?
F2 P1 F5 86.2(2) . . ?
F3 P1 F5 87.00(17) . . ?
C13 O1 C16 117.9(4) . . ?
C1 N1 C3 108.5(3) . . ?
C1 N1 C4 124.0(3) . . ?
C3 N1 C4 127.4(3) . . ?
C1 N2 C2 107.4(3) . . ?
C1 N2 C10 124.5(3) . . ?
C2 N2 C10 128.0(3) . . ?
O3 N3 O2 123.2(4) . . ?
O3 N3 C9 117.0(4) . . ?
O2 N3 C9 119.8(3) . . ?
O4 N4 O5 126.8(6) . . ?
O4 N4 C7 118.1(6) . . ?
O5 N4 C7 115.1(6) . . ?
P1 F2 H1 100.6 . . ?
N2 C1 N1 109.4(3) . . ?
N2 C1 H1 125.3 . . ?
N1 C1 H1 125.3 . . ?
C3 C2 N2 108.2(3) . . ?
C3 C2 H2 125.9 . . ?
N2 C2 H2 125.9 . . ?
C2 C3 N1 106.5(3) . . ?
C2 C3 H3 126.8 . . ?
N1 C3 H3 126.8 . . ?
C5 C4 C9 119.8(3) . . ?
C5 C4 N1 117.7(3) . . ?
C9 C4 N1 122.4(3) . . ?
C4 C5 C6 120.2(4) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C7 C6 C5 117.8(4) . . ?
C7 C6 H6 121.1 . . ?
C5 C6 H6 121.1 . . ?
C8 C7 C6 124.5(4) . . ?
C8 C7 N4 116.7(5) . . ?
C6 C7 N4 118.8(4) . . ?
C7 C8 C9 117.9(4) . . ?
C7 C8 H8 121.1 . . ?
C9 C8 H8 121.1 . . ?
C4 C9 C8 119.7(3) . . ?
C4 C9 N3 123.0(3) . . ?
C8 C9 N3 117.3(3) . . ?
C15 C10 C11 120.0(3) . . ?
C15 C10 N2 119.5(3) . . ?
C11 C10 N2 120.4(3) . . ?
C10 C11 C12 119.4(4) . . ?
C10 C11 H11 120.3 . . ?
C12 C11 H11 120.3 . . ?
C13 C12 C11 120.9(4) . . ?
C13 C12 H12 119.5 . . ?
C11 C12 H12 119.5 . . ?
O1 C13 C12 125.4(4) . . ?
O1 C13 C14 115.2(4) . . ?
C12 C13 C14 119.4(3) . . ?
C15 C14 C13 120.0(4) . . ?
C15 C14 H14 120.0 . . ?
C13 C14 H14 120.0 . . ?
C14 C15 C10 120.2(4) . . ?
C14 C15 H15 119.9 . . ?
C10 C15 H15 119.9 . . ?
O1 C16 H16A 109.5 . . ?
O1 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
O1 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?

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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
F1 P1 F2 H1 -14.3 . . . . ?
F6 P1 F2 H1 -137.4 . . . . ?
F4 P1 F2 H1 132.7 . . . . ?
F3 P1 F2 H1 -45.9 . . . . ?
F5 P1 F2 H1 41.2 . . . . ?
C2 N2 C1 N1 -1.2(4) . . . . ?
C10 N2 C1 N1 177.4(3) . . . . ?
C3 N1 C1 N2 1.3(4) . . . . ?
C4 N1 C1 N2 -175.5(3) . . . . ?
C1 N2 C2 C3 0.6(5) . . . . ?
C10 N2 C2 C3 -177.9(3) . . . . ?
N2 C2 C3 N1 0.2(5) . . . . ?
C1 N1 C3 C2 -0.9(4) . . . . ?
C4 N1 C3 C2 175.8(3) . . . . ?
C1 N1 C4 C5 -103.5(4) . . . . ?
C3 N1 C4 C5 80.3(4) . . . . ?
C1 N1 C4 C9 73.5(4) . . . . ?
C3 N1 C4 C9 -102.8(4) . . . . ?
C9 C4 C5 C6 -1.7(5) . . . . ?
N1 C4 C5 C6 175.4(3) . . . . ?
C4 C5 C6 C7 -1.0(5) . . . . ?
C5 C6 C7 C8 2.4(6) . . . . ?
C5 C6 C7 N4 -177.2(4) . . . . ?
O4 N4 C7 C8 -27.3(6) . . . . ?
O5 N4 C7 C8 152.9(4) . . . . ?
O4 N4 C7 C6 152.4(5) . . . . ?
O5 N4 C7 C6 -27.5(6) . . . . ?
C6 C7 C8 C9 -1.1(6) . . . . ?
N4 C7 C8 C9 178.5(3) . . . . ?
C5 C4 C9 C8 3.0(5) . . . . ?
N1 C4 C9 C8 -173.9(3) . . . . ?
C5 C4 C9 N3 -176.0(3) . . . . ?
N1 C4 C9 N3 7.1(5) . . . . ?
C7 C8 C9 C4 -1.7(5) . . . . ?
C7 C8 C9 N3 177.4(3) . . . . ?
O3 N3 C9 C4 177.3(3) . . . . ?
O2 N3 C9 C4 -2.3(5) . . . . ?
O3 N3 C9 C8 -1.8(5) . . . . ?
O2 N3 C9 C8 178.6(3) . . . . ?
C1 N2 C10 C15 -33.8(5) . . . . ?
C2 N2 C10 C15 144.5(4) . . . . ?
C1 N2 C10 C11 145.6(4) . . . . ?
C2 N2 C10 C11 -36.2(6) . . . . ?
C15 C10 C11 C12 -1.5(6) . . . . ?
N2 C10 C11 C12 179.2(4) . . . . ?
C10 C11 C12 C13 1.6(7) . . . . ?
C16 O1 C13 C12 -4.9(6) . . . . ?
C16 O1 C13 C14 175.9(4) . . . . ?
C11 C12 C13 O1 -179.4(4) . . . . ?
C11 C12 C13 C14 -0.2(7) . . . . ?
O1 C13 C14 C15 178.0(3) . . . . ?
C12 C13 C14 C15 -1.3(6) . . . . ?
C13 C14 C15 C10 1.4(6) . . . . ?
C11 C10 C15 C14 -0.1(6) . . . . ?
N2 C10 C15 C14 179.3(3) . . . . ?

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
C3 H3 F3 0.93 2.59 3.341(5) 138.2 4_565
C5 H5 F2 0.93 2.55 3.127(5) 120.2 3_655
C12 H12 F4 0.93 2.47 3.331(5) 154.1 1_655
C15 H15 F2 0.93 2.83 3.491(5) 129.3 .
C1 H1 F5 0.93 2.53 3.278(5) 138.1 .
C1 H1 F3 0.93 2.66 3.307(5) 127.3 .
C1 H1 F2 0.93 2.51 3.429(5) 169.4 .

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        27.00
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.626
_refine_diff_density_min         -0.352
_refine_diff_density_rms         0.066