#------------------------------------------------------------------------------
#$Date: 2011-09-10 05:16:28 +0200 (Sat, 10 Sep 2011) $
#$Revision: 25271 $
#$URL: svn://www.crystallography.net/cod/cif/2/2009128.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_2009128
loop_
_publ_author_name
'Vergeer, P.'
'Kooijman, H.'
'Schreurs, A. M. M.'
'Kroon, J.'
'Grech, E.'
_publ_section_title
;
 1,8-Bis(dimethylamino)naphthalene
 bis[6-fluoro-2-(trifluoromethyl)-4-quinolinol] acetonitrile solvate
;
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1822
_journal_page_last               1824
_journal_volume                  55
_journal_year                    1999
_chemical_formula_moiety
'C14 H19 N2 +, C10 H4 F4 N O -, C10 H5 F4 N O, C2 H3 N'
_chemical_formula_sum            'C36 H31 F8 N5 O2'
_chemical_formula_weight         717.66
_chemical_name_systematic
;
(8-Dimethylamino-1-naphtyl)dimethylammonium
6-fluoro-2-(trifluoromethyl)-4-quinolinolate
-6-fluoro-2-(trifluoromethyl)-4-quinolinol
;
_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'
_cell_angle_alpha                90
_cell_angle_beta                 90.578(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.8833(10)
_cell_length_b                   17.9581(10)
_cell_length_c                   19.2752(10)
_cell_measurement_reflns_used    47
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      24.523
_cell_measurement_theta_min      4.808
_cell_volume                     3420.9(4)
_computing_cell_refinement       'DIRAX (Duisenberg, 1992)'
_computing_data_collection       'Kappa CCD Server (Nonius B.V., 1997)'
_computing_data_reduction        'EVAL (Schreurs & Duisenberg, 1999)'
_computing_molecular_graphics    'PLATON (Spek, 1990)'
_computing_publication_material  'PLATON (Spek, 1990)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997b)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997a)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Nonius Kappa CCD diffractometer'
_diffrn_measurement_method       'area detector \q and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71730
_diffrn_reflns_av_R_equivalents  0.0619
_diffrn_reflns_av_sigmaI/netI    0.0617
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            11065
_diffrn_reflns_reduction_process
;
 ?
;
_diffrn_reflns_theta_full        27.80
_diffrn_reflns_theta_max         27.80
_diffrn_reflns_theta_min         2.13
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.129
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.393
_exptl_crystal_density_meas      'Not measured'
_exptl_crystal_density_method    'Not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1480
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.189
_refine_diff_density_min         -0.261
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.119
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         3014
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.119
_refine_ls_R_factor_all          0.0896
_refine_ls_R_factor_gt           0.0580
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[^2^(F~O~^2^)+(0.0427P)^2^+4.0310P] where P=(F~O~^2^+2F~C~^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1200
_reflns_number_gt                2630
_reflns_number_total             3939
_reflns_threshold_expression     I>2\s(I)
_[local]_cod_data_source_file    gd1044.cif
_[local]_cod_data_source_block   a075a
_[local]_cod_cif_authors_sg_H-M  'C 2/c'
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from
2010-06-29.

'_exptl_absorpt_correction_type' value 'None' changed to
'none' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               2009128
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,y,1/2-z
-x,-y,-z
x,-y,1/2+z
1/2+x,1/2+y,z
1/2-x,1/2+y,1/2-z
1/2-x,1/2-y,-z
1/2+x,1/2-y,1/2+z
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
N1 0.0192(12) 0.0225(12) 0.0191(11) -0.0043(9) 0.0013(9) -0.0016(9)
C1 0.0152(13) 0.0257(14) 0.0205(13) 0.0008(11) -0.0060(10) -0.0031(11)
C2 0.0146(18) 0.026(2) 0.0192(18) 0.0000 -0.0095(14) 0.0000
C3 0.028(2) 0.024(2) 0.028(2) 0.0000 -0.0173(17) 0.0000
C4 0.0458(19) 0.0189(15) 0.0372(17) 0.0089(13) -0.0159(14) -0.0082(13)
C5 0.0345(18) 0.0355(18) 0.0335(17) 0.0142(14) -0.0064(13) -0.0145(14)
C6 0.0250(16) 0.0387(18) 0.0244(14) 0.0049(13) 0.0000(11) -0.0043(13)
C7 0.0239(16) 0.042(2) 0.0440(18) -0.0113(14) 0.0007(14) -0.0117(16)
C8 0.0366(17) 0.0291(17) 0.0211(14) -0.0017(13) 0.0024(13) 0.0040(12)
F1 0.0360(10) 0.0173(8) 0.0480(10) -0.0006(7) -0.0062(7) -0.0040(7)
F2 0.0312(10) 0.0221(9) 0.0697(12) -0.0035(7) 0.0031(8) -0.0057(8)
F3 0.0520(11) 0.0390(10) 0.0476(10) -0.0096(8) 0.0175(9) -0.0225(8)
F4 0.0801(15) 0.0293(10) 0.0654(12) 0.0238(9) -0.0392(11) -0.0051(9)
O2 0.0144(10) 0.0366(12) 0.0269(10) 0.0036(8) -0.0059(8) -0.0087(9)
N2 0.0181(11) 0.0191(11) 0.0226(11) 0.0008(9) -0.0020(8) -0.0018(9)
C9 0.0173(13) 0.0233(14) 0.0144(12) 0.0002(10) -0.0015(10) 0.0009(10)
C10 0.0167(14) 0.0267(15) 0.0253(14) 0.0009(11) -0.0058(11) -0.0028(12)
C11 0.0214(15) 0.0202(14) 0.0314(15) 0.0036(11) -0.0058(11) 0.0016(11)
C12 0.0269(15) 0.0169(14) 0.0236(13) -0.0022(11) -0.0002(11) -0.0019(11)
C13 0.0195(14) 0.0275(15) 0.0164(12) -0.0058(11) -0.0022(10) -0.0024(11)
C14 0.0150(13) 0.0251(14) 0.0134(12) 0.0005(10) 0.0003(9) 0.0003(10)
C15 0.0149(13) 0.0319(15) 0.0133(12) 0.0020(11) -0.0006(10) -0.0029(11)
C16 0.0168(14) 0.0262(15) 0.0222(13) 0.0081(11) -0.0012(10) -0.0017(11)
C17 0.0172(14) 0.0238(14) 0.0188(13) 0.0038(11) 0.0000(10) -0.0014(11)
C18 0.0226(15) 0.0250(15) 0.0304(15) 0.0040(12) -0.0058(12) -0.0020(12)
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
_atom_site_occupancy
_atom_site_type_symbol
N1 0.5843(2) 0.34993(11) 0.20020(10) 0.0203(7) Uani 1.000 N
C1 0.5854(2) 0.26869(14) 0.20161(12) 0.0205(8) Uani 1.000 C
C2 0.50000 0.2318(2) 0.25000 0.0200(11) Uani 1.000 C
C3 0.50000 0.1522(2) 0.25000 0.0268(12) Uani 1.000 C
C4 0.5849(3) 0.11379(16) 0.20353(15) 0.0341(10) Uani 1.000 C
C5 0.6651(3) 0.15108(17) 0.15793(15) 0.0345(10) Uani 1.000 C
C6 0.6643(3) 0.22865(17) 0.15707(14) 0.0294(9) Uani 1.000 C
C7 0.7190(3) 0.38249(19) 0.21569(18) 0.0366(10) Uani 1.000 C
C8 0.5267(3) 0.37917(17) 0.13400(14) 0.0289(9) Uani 1.000 C
F1 0.18120(15) -0.00102(8) 0.04120(8) 0.0338(5) Uani 1.000 F
F2 0.21310(15) 0.44581(8) 0.10992(9) 0.0410(6) Uani 1.000 F
F3 0.03543(17) 0.42841(9) 0.16896(9) 0.0461(6) Uani 1.000 F
F4 0.0197(2) 0.46306(9) 0.06280(10) 0.0585(7) Uani 1.000 F
O2 -0.15911(17) 0.20544(10) 0.01207(9) 0.0260(6) Uani 1.000 O
N2 0.1902(2) 0.29867(11) 0.09932(10) 0.0199(6) Uani 1.000 N
C9 0.1827(2) 0.22432(14) 0.08325(11) 0.0183(8) Uani 1.000 C
C10 0.2980(3) 0.17937(14) 0.09611(13) 0.0229(8) Uani 1.000 C
C11 0.2964(3) 0.10505(14) 0.08219(13) 0.0244(8) Uani 1.000 C
C12 0.1788(3) 0.07354(13) 0.05466(12) 0.0225(8) Uani 1.000 C
C13 0.0644(3) 0.11280(14) 0.04118(12) 0.0211(8) Uani 1.000 C
C14 0.0648(2) 0.19027(13) 0.05448(11) 0.0178(8) Uani 1.000 C
C15 -0.0504(2) 0.23654(14) 0.03888(11) 0.0200(8) Uani 1.000 C
C16 -0.0381(3) 0.31170(15) 0.05393(12) 0.0217(8) Uani 1.000 C
C17 0.0814(2) 0.33816(14) 0.08403(12) 0.0199(8) Uani 1.000 C
C18 0.0887(3) 0.41870(15) 0.10527(13) 0.0260(9) Uani 1.000 C
H1 0.522(7) 0.364(3) 0.238(4) 0.0410 Uiso 0.500 H
H4 0.584(3) 0.0611(17) 0.2063(14) 0.0410 Uiso 1.000 H
H5 0.721(3) 0.1241(16) 0.1263(15) 0.0410 Uiso 1.000 H
H6 0.718(3) 0.2549(16) 0.1265(14) 0.0350 Uiso 1.000 H
H7A 0.753(3) 0.3622(18) 0.2599(18) 0.0550 Uiso 1.000 H
H7B 0.710(3) 0.4382(19) 0.2209(16) 0.0550 Uiso 1.000 H
H7C 0.784(3) 0.3706(17) 0.1788(17) 0.0550 Uiso 1.000 H
H8A 0.586(3) 0.3666(16) 0.0946(16) 0.0430 Uiso 1.000 H
H8B 0.518(3) 0.4337(18) 0.1384(15) 0.0430 Uiso 1.000 H
H8C 0.442(3) 0.3554(17) 0.1277(15) 0.0430 Uiso 1.000 H
H2 -0.219(7) 0.236(4) 0.001(4) 0.0390 Uiso 0.500 H
H10 0.378(3) 0.2019(14) 0.1148(13) 0.0280 Uiso 1.000 H
H11 0.371(3) 0.0740(15) 0.0919(13) 0.0290 Uiso 1.000 H
H13 -0.014(3) 0.0881(14) 0.0202(13) 0.0250 Uiso 1.000 H
H16 -0.109(3) 0.3454(14) 0.0436(13) 0.0260 Uiso 1.000 H
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
O O 0.0106 0.0060 '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'
F F 0.0171 0.0103 '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'
C C 0.0033 0.0016 '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
C15 O2 H2 . . 113(5) yes
C1 N1 C8 . . 111.81(19) yes
C7 N1 C8 . . 111.6(2) yes
C1 N1 C7 . . 112.6(2) yes
C7 N1 H1 . . 108(4) no
C1 N1 H1 . . 104(3) no
C8 N1 H1 . . 108(4) no
C9 N2 C17 . . 115.5(2) no
N1 C1 C6 . . 121.2(2) yes
C2 C1 C6 . . 120.7(3) no
N1 C1 C2 . . 118.2(2) yes
C1 C2 C1 . 2_655 124.7(3) no
C1 C2 C3 2_655 . 117.66(16) no
C1 C2 C3 . . 117.66(16) no
C2 C3 C4 . . 119.21(17) no
C2 C3 C4 . 2_655 119.21(17) no
C4 C3 C4 . 2_655 121.6(3) no
C3 C4 C5 . . 121.4(3) no
C4 C5 C6 . . 119.7(3) no
C1 C6 C5 . . 121.4(3) no
C5 C4 H4 . . 122.1(17) no
C3 C4 H4 . . 116.5(17) no
C4 C5 H5 . . 120.3(17) no
C6 C5 H5 . . 120.1(17) no
C5 C6 H6 . . 120.9(18) no
C1 C6 H6 . . 117.7(18) no
N1 C7 H7B . . 109.3(17) no
H7A C7 H7B . . 108(3) no
H7A C7 H7C . . 109(3) no
N1 C7 H7C . . 111.1(18) no
H7B C7 H7C . . 110(2) no
N1 C7 H7A . . 109.1(18) no
N1 C8 H8C . . 106.3(18) no
N1 C8 H8A . . 110.7(18) no
H8A C8 H8C . . 109(2) no
H8B C8 H8C . . 112(3) no
H8A C8 H8B . . 110(2) no
N1 C8 H8B . . 108.0(17) no
N2 C9 C14 . . 123.2(2) no
C10 C9 C14 . . 118.5(2) no
N2 C9 C10 . . 118.3(2) no
C9 C10 C11 . . 121.1(3) no
C10 C11 C12 . . 118.8(3) no
F1 C12 C11 . . 117.1(2) no
F1 C12 C13 . . 119.4(2) no
C11 C12 C13 . . 123.6(2) no
C12 C13 C14 . . 118.4(2) no
C9 C14 C13 . . 119.6(2) no
C13 C14 C15 . . 122.0(2) no
C9 C14 C15 . . 118.4(2) no
O2 C15 C16 . . 124.5(2) yes
C14 C15 C16 . . 116.8(2) no
O2 C15 C14 . . 118.7(2) yes
C15 C16 C17 . . 119.4(2) no
N2 C17 C16 . . 126.5(2) no
N2 C17 C18 . . 114.8(2) no
C16 C17 C18 . . 118.6(2) no
F2 C18 F4 . . 107.0(2) no
F2 C18 C17 . . 114.4(2) no
F2 C18 F3 . . 105.1(2) no
F3 C18 C17 . . 110.7(2) no
F4 C18 C17 . . 112.7(2) no
F3 C18 F4 . . 106.3(2) no
C9 C10 H10 . . 119.1(16) no
C11 C10 H10 . . 119.8(16) no
C10 C11 H11 . . 122.3(17) no
C12 C11 H11 . . 118.9(17) no
C12 C13 H13 . . 120.0(16) no
C14 C13 H13 . . 121.5(16) no
C15 C16 H16 . . 121.1(16) no
C17 C16 H16 . . 119.5(16) no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
F1 C12 1.364(3) no
F2 C18 1.325(3) no
F3 C18 1.352(3) no
F4 C18 1.326(3) no
O2 C15 1.312(3) yes
O2 H2 0.83(7) no
N1 C8 1.488(3) yes
N1 C7 1.482(4) yes
N1 C1 1.459(3) yes
N1 H1 0.99(7) no
N2 C17 1.319(3) yes
N2 C9 1.372(3) yes
C1 C2 1.427(3) no
C1 C6 1.370(4) no
C2 C3 1.429(5) no
C3 C4 1.413(3) no
C4 C5 1.365(4) no
C5 C6 1.393(4) no
C4 H4 0.95(3) no
C5 H5 0.96(3) no
C6 H6 0.93(3) no
C7 H7A 0.98(3) no
C7 H7B 1.01(3) no
C7 H7C 0.99(3) no
C8 H8B 0.99(3) no
C8 H8C 0.95(3) no
C8 H8A 0.99(3) no
C9 C14 1.423(3) no
C9 C10 1.416(4) no
C10 C11 1.361(4) no
C11 C12 1.393(4) no
C12 C13 1.355(4) no
C13 C14 1.415(3) no
C14 C15 1.439(3) no
C15 C16 1.386(4) no
C16 C17 1.394(4) no
C17 C18 1.505(4) yes
C10 H10 0.96(3) no
C11 H11 0.94(3) no
C13 H13 0.98(3) no
C16 H16 0.95(3) no
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
F1 C8 3.196(3) 5_445 no
F2 C8 3.350(3) . no
F2 N2 2.660(2) . no
F3 C7 3.366(3) 1_455 no
F3 N2 3.100(3) . no
F4 F4 2.785(3) 3_565 no
F1 H8B 2.75(3) 5_445 no
F1 H8A 2.76(3) 5_445 no
F1 H13 2.56(3) 3_555 no
F2 H8C 2.80(3) . no
F3 H7C 2.70(3) 1_455 no
F3 H4 2.53(3) 5_455 no
F3 H7A 2.76(3) 2_655 no
F4 H16 2.49(3) . no
F4 H11 2.54(3) 5_455 no
O2 C6 3.336(3) 1_455 no
O2 O2 2.447(2) 7_455 no
O2 C16 3.255(3) 7_455 no
O2 C15 3.199(3) 7_455 no
O2 H5 2.90(3) 1_455 no
O2 H13 2.55(3) . no
O2 H2 1.62(7) 7_455 no
O2 H6 2.82(3) 7_555 no
O2 H8A 2.54(3) 7_555 no
O2 H16 2.68(3) 7_455 no
O2 H6 2.68(3) 1_455 no
N1 C8 3.430(3) 2_655 no
N1 N1 2.555(3) 2_655 no
N2 F3 3.100(3) . no
N2 F2 2.660(2) . no
N1 H1 1.62(7) 2_655 no
N2 H8C 2.74(3) . no
C3 C10 3.592(3) 2_655 no
C3 C10 3.592(3) . no
C6 O2 3.336(3) 1_655 no
C7 F3 3.366(3) 1_655 no
C8 C13 3.489(4) 7_555 no
C8 F1 3.196(3) 5_555 no
C8 F2 3.350(3) . no
C8 N1 3.430(3) 2_655 no
C10 C3 3.592(3) . no
C10 C3 3.592(3) . no
C11 C17 3.584(3) 7_555 no
C13 C8 3.489(4) 7_555 no
C15 O2 3.199(3) 7_455 no
C16 O2 3.254(3) 7_455 no
C17 C11 3.584(3) 7_555 no
C1 H10 2.89(3) . no
C1 H1 2.33(6) 2_655 no
C2 H10 2.91(3) . no
C2 H10 2.91(3) 2_655 no
C3 H10 3.00(3) . no
C3 H10 3.00(3) 2_655 no
C4 H10 3.09(3) . no
C4 H11 3.09(3) . no
C5 H10 3.09(3) . no
C6 H8A 2.86(3) . no
C6 H10 2.98(3) . no
C6 H7C 2.84(3) . no
C7 H1 2.57(7) 2_655 no
C7 H6 2.86(3) . no
C8 H1 2.53(8) 2_655 no
C8 H6 2.93(3) . no
C8 H13 3.03(3) 7_555 no
C13 H8A 3.02(3) 7_555 no
C15 H2 2.45(7) 7_455 no
C15 H6 2.88(3) 1_455 no
C16 H6 2.98(3) 1_455 no
C16 H2 2.75(7) 7_455 no
H1 C1 2.33(6) 2_655 no
H1 N1 1.62(7) 2_655 no
H1 C7 2.57(7) 2_655 no
H1 C8 2.53(8) 2_655 no
H2 O2 1.62(7) 7_455 no
H2 C15 2.45(7) 7_455 no
H2 C16 2.75(7) 7_455 no
H2 H6 2.46(8) 7_555 no
H2 H16 2.40(8) 7_455 no
H2 H6 2.53(8) 1_455 no
H2 H16 2.39(8) . no
H4 H4 2.38(4) 2_655 no
H4 F3 2.53(3) 5_545 no
H5 O2 2.90(3) 1_655 no
H6 O2 2.68(3) 1_655 no
H6 C7 2.86(3) . no
H6 C8 2.93(3) . no
H6 C15 2.88(3) 1_655 no
H6 C16 2.98(3) 1_655 no
H6 H2 2.53(8) 1_655 no
H6 H7C 2.40(4) . no
H6 H8A 2.47(4) . no
H6 O2 2.82(3) 7_555 no
H6 H2 2.46(8) 7_555 no
H7A F3 2.76(3) 2_655 no
H7B H8B 2.46(4) . no
H7C H6 2.40(4) . no
H7C H8A 2.53(4) . no
H7C C6 2.84(3) . no
H7C F3 2.70(3) 1_655 no
H8A C6 2.86(3) . no
H8A F1 2.76(3) 5_555 no
H8A H6 2.47(4) . no
H8A H7C 2.53(4) . no
H8A H13 2.46(4) 7_555 no
H8A O2 2.54(3) 7_555 no
H8A C13 3.02(3) 7_555 no
H8B H7B 2.46(4) . no
H8B F1 2.75(3) 5_555 no
H8C N2 2.74(3) . no
H8C F2 2.80(3) . no
H10 C1 2.89(3) . no
H10 C2 2.91(3) . no
H10 C3 3.00(3) . no
H10 C4 3.09(3) . no
H10 C5 3.09(3) . no
H10 C6 2.98(3) . no
H10 C2 2.91(3) . no
H10 C3 3.00(3) . no
H11 C4 3.09(3) . no
H11 F4 2.54(3) 5_545 no
H13 O2 2.55(3) . no
H13 F1 2.56(3) 3_555 no
H13 C8 3.03(3) 7_555 no
H13 H8A 2.46(4) 7_555 no
H16 F4 2.49(3) . no
H16 H2 2.39(8) . no
H16 O2 2.68(3) 7_455 no
H16 H2 2.40(8) 7_455 no
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
_geom_hbond_publ_flag
N1 H1 N1 2_655 0.99(7) 1.62(7) 2.555(3) 156(5) yes
O2 H2 O2 7_455 0.83(7) 1.62(7) 2.447(2) 174(8) yes
C4 H4 F3 5_545 0.95(3) 2.53(3) 3.429(3) 158(2) yes
C8 H8A O2 7_555 0.99(3) 2.54(3) 3.467(3) 156(2) yes
C11 H11 F4 5_545 0.94(3) 2.54(3) 3.395(3) 151(2) yes
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_4
_geom_torsion
_geom_torsion_publ_flag
C8 N1 C1 C2 . . -113.4(2) no
C8 N1 C1 C6 . . 65.5(3) no
C7 N1 C1 C2 . . 119.9(2) no
C7 N1 C1 C6 . . -61.1(3) no
C9 N2 C17 C16 . . 0.3(3) no
C9 N2 C17 C18 . . 177.0(2) no
C17 N2 C9 C14 . . -2.3(3) no
C17 N2 C9 C10 . . 177.8(2) no
N1 C1 C2 C1 . 2_655 -1.2(2) no
C6 C1 C2 C1 . 2_655 179.9(3) no
C6 C1 C2 C3 . . -0.1(2) no
N1 C1 C6 C5 . . -179.6(2) yes
C2 C1 C6 C5 . . -0.7(4) no
N1 C1 C2 C3 . . 178.83(13) yes
C1 C2 C3 C4 . . 0.98(16) no
C1 C2 C3 C4 . 2_655 -179.02(17) no
C1 C2 C3 C4 2_655 . -179.02(17) no
C2 C3 C4 C5 . . -1.1(3) no
C4 C3 C4 C5 2_655 . 178.9(2) no
C3 C4 C5 C6 . . 0.3(4) no
C4 C5 C6 C1 . . 0.6(4) no
C14 C9 C10 C11 . . -0.8(4) no
N2 C9 C10 C11 . . 179.1(2) no
C10 C9 C14 C13 . . 1.6(3) no
N2 C9 C14 C13 . . -178.3(2) no
N2 C9 C14 C15 . . 2.6(3) no
C10 C9 C14 C15 . . -177.6(2) no
C9 C10 C11 C12 . . 0.2(4) no
C10 C11 C12 C13 . . -0.4(4) no
C10 C11 C12 F1 . . 179.8(3) no
F1 C12 C13 C14 . . -179.0(2) no
C11 C12 C13 C14 . . 1.2(4) no
C12 C13 C14 C9 . . -1.8(3) no
C12 C13 C14 C15 . . 177.3(2) no
C13 C14 C15 O2 . . 0.6(3) no
C13 C14 C15 C16 . . -179.8(2) no
C9 C14 C15 C16 . . -0.6(3) no
C9 C14 C15 O2 . . 179.71(17) no
O2 C15 C16 C17 . . 178.4(2) no
C14 C15 C16 C17 . . -1.2(3) no
C15 C16 C17 N2 . . 1.5(4) no
C15 C16 C17 C18 . . -175.1(2) no
N2 C17 C18 F3 . . -92.9(3) no
N2 C17 C18 F4 . . 148.2(2) no
C16 C17 C18 F3 . . 84.2(3) no
C16 C17 C18 F4 . . -34.7(3) no
C16 C17 C18 F2 . . -157.3(2) no
N2 C17 C18 F2 . . 25.7(3) no