#------------------------------------------------------------------------------
#$Date: 2019-11-27 02:11:13 +0200 (Wed, 27 Nov 2019) $
#$Revision: 243746 $
#$URL: svn://www.crystallography.net/cod/cif/4/03/76/4037617.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_4037617
loop_
_publ_author_name
'Bugera, Maksym'
'Trofymchuk, Serhii'
'Tarasenko, Karen'
'Zaporozhets, Olga'
'Pustovit, Yurii'
'Mykhailiuk, Pavel K.'
_publ_section_title
;
 Deoxofluorination of Aliphatic Carboxylic Acids: a Route to
 Trifluoromethyl-Substituted Derivatives.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.9b02596
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_moiety         'K(ClO4)5, 4(C6 H11 F3 N), 1.26 (H2 O)'
_chemical_formula_sum            'C24 H46.52 Cl5 F12 K N4 O21.27'
_chemical_formula_weight         1175.84
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2016/4
_cell_angle_alpha                90
_cell_angle_beta                 130.76
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   23.336(8)
_cell_length_b                   7.0039(17)
_cell_length_c                   17.870(6)
_cell_measurement_reflns_used    566
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      19.23
_cell_measurement_theta_min      2.30
_cell_volume                     2212.3(12)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2016/4 (Sheldrick, 2016)'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      123(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0695
_diffrn_reflns_av_unetI/netI     0.0892
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            10320
_diffrn_reflns_point_group_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        25.018
_diffrn_reflns_theta_max         25.018
_diffrn_reflns_theta_min         1.745
_exptl_absorpt_coefficient_mu    0.554
_exptl_absorpt_correction_T_max  0.97
_exptl_absorpt_correction_T_min  0.56
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.765
_exptl_crystal_description       needle
_exptl_crystal_F_000             1201
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.060
_refine_diff_density_max         1.442
_refine_diff_density_min         -1.080
_refine_diff_density_rms         0.102
_refine_ls_abs_structure_details
;
 Flack x determined using 1029 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.00(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     360
_refine_ls_number_reflns         3857
_refine_ls_number_restraints     15
_refine_ls_restrained_S_all      1.084
_refine_ls_R_factor_all          0.0948
_refine_ls_R_factor_gt           0.0755
_refine_ls_shift/su_max          0.030
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1177P)²+2.8865P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1904
_refine_ls_wR_factor_ref         0.2064
_reflns_Friedel_coverage         0.803
_reflns_Friedel_fraction_full    0.960
_reflns_Friedel_fraction_max     0.960
_reflns_number_gt                3086
_reflns_number_total             3857
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo9b02596_si_003.cif
_cod_data_source_block           xr33
_cod_original_cell_volume        2212.2(12)
_cod_original_sg_symbol_H-M      'C 2'
_cod_database_code               4037617
_shelx_shelxl_version_number     2016/4
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.769
_shelx_estimated_absorpt_t_max   0.967
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
K1 K 0.000000 -0.0159(4) 0.000000 0.0265(7) Uani 1 2 d S T P A .
CL1 Cl 0.12179(12) -0.0799(4) 0.25958(15) 0.0296(6) Uani 1 1 d . . . . .
O1A O 0.1439(6) -0.2567(17) 0.3040(8) 0.044(3) Uani 0.718(10) 1 d . . P A 1
O2A O 0.1427(5) -0.0581(14) 0.1981(6) 0.034(2) Uani 0.718(10) 1 d . . P A 1
O3A O 0.0399(5) -0.0609(14) 0.1942(6) 0.035(2) Uani 0.718(10) 1 d . . P A 1
O4A O 0.1552(6) 0.0761(19) 0.3283(8) 0.051(3) Uani 0.718(10) 1 d . . P A 1
O1B O 0.198(2) -0.079(7) 0.347(3) 0.085(11) Uiso 0.282(10) 1 d . . P A 2
O2B O 0.1030(16) -0.242(5) 0.200(2) 0.054(8) Uiso 0.282(10) 1 d . . P A 2
O3B O 0.0979(15) 0.087(5) 0.211(2) 0.051(8) Uiso 0.282(10) 1 d . . P A 2
O4B O 0.078(2) -0.128(6) 0.294(3) 0.089(13) Uiso 0.282(10) 1 d . . P A 2
CL2 Cl 0.000000 0.4780(4) 0.000000 0.0188(6) Uani 1 2 d DS T P . .
O6A O 0.0543(5) 0.3594(13) 0.0074(7) 0.024(3) Uani 0.631(14) 1 d D . P A 3
O5A O -0.0391(5) 0.5943(13) -0.0861(6) 0.022(3) Uani 0.631(14) 1 d D . P A 3
O6B O 0.0505(8) 0.601(2) 0.0020(12) 0.028(5) Uiso 0.369(14) 1 d D . P A 4
O5B O 0.0427(8) 0.369(2) 0.0879(9) 0.024(5) Uiso 0.369(14) 1 d D . P A 4
CL3A Cl 0.1726(5) -0.0332(12) 0.0139(6) 0.062(2) Uani 0.631(10) 1 d D . P A 5
O7A O 0.1240(6) -0.1274(17) 0.0108(8) 0.039(3) Uani 0.631(10) 1 d D . P A 5
O8A O 0.1442(10) 0.079(2) -0.0735(9) 0.078(6) Uani 0.631(10) 1 d D . P A 5
O9A O 0.2270(9) 0.086(2) 0.1024(9) 0.080(6) Uani 0.631(10) 1 d D . P A 5
O10A O 0.2242(8) -0.155(2) 0.0220(10) 0.062(2) Uani 0.631(10) 1 d D . P A 5
O11A O 0.1864(6) 0.4782(17) 0.0180(8) 0.029(2) Uani 0.631(10) 1 d D . P A 5
H11O H 0.189(10) 0.362(5) 0.020(13) 0.035 Uiso 0.631(10) 1 d D U P A 5
H12O H 0.218(7) 0.53(2) 0.022(12) 0.035 Uiso 0.631(10) 1 d D U P A 5
CL3B Cl 0.1626(5) 0.049(2) 0.0107(6) 0.039(3) Uani 0.369(10) 1 d D . P A 6
O7B O 0.0867(11) -0.023(4) -0.0732(16) 0.069(7) Uiso 0.369(10) 1 d D . P A 6
O8B O 0.1657(16) -0.009(5) 0.0902(18) 0.087(9) Uiso 0.369(10) 1 d D . P A 6
O9B O 0.1245(17) 0.215(4) 0.009(2) 0.094(10) Uiso 0.369(10) 1 d D . P A 6
O10B O 0.194(3) 0.107(7) -0.028(3) 0.129(15) Uiso 0.369(10) 1 d D . P A 6
F4 F 0.3505(4) 0.3123(13) 0.2867(6) 0.075(2) Uani 1 1 d . . . . .
F5 F 0.3278(5) 0.1097(11) 0.3563(7) 0.080(3) Uani 1 1 d . . . . .
F6 F 0.4182(4) 0.3121(13) 0.4457(6) 0.076(3) Uani 1 1 d . . . . .
F1 F 0.4127(5) 0.7945(19) 0.2678(8) 0.112(4) Uani 1 1 d . . . . .
F2 F 0.5093(8) 0.6047(13) 0.3386(8) 0.114(4) Uani 1 1 d . . . . .
F3 F 0.5050(5) 0.7984(16) 0.4281(6) 0.095(3) Uani 1 1 d . . . . .
N1 N 0.4574(5) 1.0755(13) 0.1647(6) 0.040(2) Uani 1 1 d . . . . .
H1N H 0.484738 1.158914 0.159805 0.048 Uiso 1 1 calc R U . . .
H2N H 0.416588 1.037345 0.102645 0.048 Uiso 1 1 calc R U . . .
N2 N 0.2032(4) 0.5718(14) 0.1856(6) 0.038(2) Uani 1 1 d . . . . .
H3N H 0.187424 0.530242 0.126549 0.046 Uiso 1 1 calc R U . . .
H4N H 0.166651 0.649503 0.173539 0.046 Uiso 1 1 calc R U . . .
C1 C 0.5054(6) 0.9051(16) 0.2255(7) 0.036(2) Uani 1 1 d . . . . .
H1A H 0.551818 0.902391 0.234090 0.043 Uiso 1 1 calc R U . . .
H1B H 0.476955 0.785253 0.192838 0.043 Uiso 1 1 calc R U . . .
C2 C 0.4996(8) 1.1326(19) 0.3228(9) 0.054(3) Uani 1 1 d . . . . .
H2A H 0.483925 1.142576 0.362444 0.065 Uiso 1 1 calc R U . . .
H2B H 0.540738 1.225501 0.348381 0.065 Uiso 1 1 calc R U . . .
C3 C 0.5259(6) 0.9267(16) 0.3265(8) 0.038(2) Uani 1 1 d . . . . .
C4 C 0.4320(7) 1.170(2) 0.2126(8) 0.058(4) Uani 1 1 d . . . . .
H3A H 0.385059 1.110835 0.192048 0.069 Uiso 1 1 calc R U . . .
H3B H 0.423625 1.307972 0.197723 0.069 Uiso 1 1 calc R U . . .
C5 C 0.6111(6) 0.912(2) 0.4128(8) 0.052(3) Uani 1 1 d . . . . .
H5A H 0.637333 1.008341 0.404748 0.078 Uiso 1 1 calc R U . . .
H5B H 0.621863 0.935175 0.475005 0.078 Uiso 1 1 calc R U . . .
H5C H 0.628797 0.784744 0.413860 0.078 Uiso 1 1 calc R U . . .
C6 C 0.4883(9) 0.784(3) 0.3401(11) 0.079(5) Uani 1 1 d . . . . .
C7 C 0.2141(5) 0.4040(17) 0.2460(7) 0.036(2) Uani 1 1 d . . . . .
H7A H 0.211141 0.282989 0.214911 0.043 Uiso 1 1 calc R U . . .
H7B H 0.174922 0.402464 0.252090 0.043 Uiso 1 1 calc R U . . .
C8 C 0.2941(5) 0.4290(15) 0.3491(6) 0.031(2) Uani 1 1 d . . . . .
C9 C 0.3143(6) 0.6356(17) 0.3466(8) 0.042(3) Uani 1 1 d . . . . .
H9A H 0.369720 0.649972 0.388154 0.051 Uiso 1 1 calc R U . . .
H9B H 0.296794 0.723474 0.371472 0.051 Uiso 1 1 calc R U . . .
C10 C 0.2737(7) 0.6798(18) 0.2374(9) 0.056(4) Uani 1 1 d . . . . .
H10A H 0.263816 0.818171 0.223333 0.067 Uiso 1 1 calc R U . . .
H10B H 0.303420 0.634177 0.219287 0.067 Uiso 1 1 calc R U . . .
C11 C 0.2928(6) 0.4020(19) 0.4317(7) 0.044(3) Uani 1 1 d . . . . .
H11A H 0.257483 0.493522 0.423993 0.066 Uiso 1 1 calc R U . . .
H11B H 0.276388 0.271731 0.429443 0.066 Uiso 1 1 calc R U . . .
H11C H 0.343609 0.423239 0.495323 0.066 Uiso 1 1 calc R U . . .
C12 C 0.3483(7) 0.289(2) 0.3604(9) 0.053(3) Uani 1 1 d . . . . .
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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
K K 0.2009 0.2494 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
O7Ae K1 O7A 148.5(5) . 2
O6Ac K1 O6A 48.6(3) . 2
O2Aa K1 O2A 168.2(4) . 2
O6Bd K1 O6B 46.6(4) 2_545 1_545
O6Bd K1 O5B 147.2(4) 2_545 .
O6Bd K1 O5B 147.2(4) 1_545 .
O6Bd K1 O5B 147.2(4) 2_545 2
O6Bd K1 O5B 147.2(4) 1_545 2
O5Bd K1 O5B 47.6(4) . 2
O3Bb K1 O3B 151.6(12) . 2
O3Bb CL1 O1B 114(2) . .
O3Bb CL1 O2B 115.1(16) . .
O1Bb CL1 O2B 113(2) . .
O1Aa CL1 O4A 113.7(7) . .
O1Aa CL1 O3A 110.2(6) . .
O4Aa CL1 O3A 108.2(6) . .
O1Aa CL1 O2A 110.0(6) . .
O4Aa CL1 O2A 107.5(6) . .
O3Aa CL1 O2A 107.0(5) . .
O3Bb CL1 O4B 110(2) . .
O1Bb CL1 O4B 104(2) . .
O2Bb CL1 O4B 99(2) . .
O3Bb CL1 K1 53.7(12) . .
O1Aa CL1 K1 123.1(5) . .
O1Bb CL1 K1 143.3(16) . .
O2Bb CL1 K1 61.9(12) . .
O4Aa CL1 K1 123.2(5) . .
O3Aa CL1 K1 55.1(4) . .
O2Aa CL1 K1 52.0(3) . .
O4Bb CL1 K1 112.3(14) . .
CL1 O2Aa K1 104.3(4) . .
CL1 O3Aa K1 101.2(4) . .
CL1 O2Bb K1 94.7(14) . .
CL1 O3Bb K1 104.9(15) . .
O5Bd CL2 O5B 114.8(13) . 2
O5Ac CL2 O5A 110.3(8) 2 .
O5Bd CL2 O6B 108.8(9) . .
O5Bd CL2 O6B 108.7(9) 2 .
O5Bd CL2 O6B 108.7(9) . 2
O5Bd CL2 O6B 108.8(9) 2 2
O6Bd CL2 O6B 106.7(14) . 2
O5Ac CL2 O6A 108.9(5) 2 .
O5Ac CL2 O6A 109.4(5) . .
O5Ac CL2 O6A 109.4(5) 2 2
O5Ac CL2 O6A 108.9(5) . 2
O6Ac CL2 O6A 110.0(8) . 2
O5Bd CL2 K1 57.4(7) . .
O5Bd CL2 K1 57.4(7) 2 .
O5Ac CL2 K1 124.8(4) 2 .
O5Ac CL2 K1 124.8(4) . .
O6Bd CL2 K1 126.7(7) . .
O6Bd CL2 K1 126.7(7) 2 .
O6Ac CL2 K1 55.0(4) . .
O6Ac CL2 K1 55.0(4) 2 .
O5Bd CL2 K1 122.6(7) . 1_565
O5Bd CL2 K1 122.6(7) 2 1_565
O5Ac CL2 K1 55.2(4) 2 1_565
O5Ac CL2 K1 55.2(4) . 1_565
O6Bd CL2 K1 53.3(7) . 1_565
O6Bd CL2 K1 53.3(7) 2 1_565
O6Ac CL2 K1 125.0(4) . 1_565
O6Ac CL2 K1 125.0(4) 2 1_565
K1 CL2 K1 180.0 . 1_565
CL2 O6Ac K1 100.7(4) . .
CL2 O5Ac K1 101.7(4) . 1_565
CL2 O6Bd K1 103.4(8) . 1_565
CL2 O5Bd K1 98.8(7) . .
O7Ae CL3Ae O10A 111.6(11) . .
O7Ae CL3Ae O8A 117.3(11) . .
O10Ae CL3Ae O8A 101.1(11) . .
O7Ae CL3Ae O9A 117.1(10) . .
O10Ae CL3Ae O9A 98.8(11) . .
O8Ae CL3Ae O9A 108.2(10) . .
CL3Ae O7Ae K1 133.3(8) . .
O10Bf CL3Bf O8B 154(2) . .
O10Bf CL3Bf O9B 106(3) . .
O8Bf CL3Bf O9B 83.3(19) . .
O10Bf CL3Bf O7B 106(2) . .
O8Bf CL3Bf O7B 99.2(17) . .
O9Bf CL3Bf O7B 86.4(17) . .
O10Bf CL3Bf K1 152(2) . .
O8Bf CL3Bf K1 53.3(12) . .
O9Bf CL3Bf K1 60.3(14) . .
O7Bf CL3Bf K1 52.7(10) . .
CL3Bf O7Bf K1 104.6(12) . .
CL3Bf O8Bf K1 104.7(14) . .
CL3Bf O9Bf K1 96.8(16) . .
C4 N1 C1 109.0(8) . .
C10 N2 C7 110.9(8) . .
N1 C1 C3 106.4(8) . .
C4 C2 C3 104.9(10) . .
C6 C3 C5 108.4(11) . .
C6 C3 C1 111.6(10) . .
C5 C3 C1 112.2(8) . .
C6 C3 C2 112.7(11) . .
C5 C3 C2 108.8(10) . .
C1 C3 C2 103.2(9) . .
N1 C4 C2 101.7(8) . .
F1 C6 F2 107.4(13) . .
F1 C6 F3 108.2(12) . .
F2 C6 F3 105.1(15) . .
F1 C6 C3 110.9(14) . .
F2 C6 C3 111.8(12) . .
F3 C6 C3 113.1(12) . .
N2 C7 C8 105.8(8) . .
C12 C8 C11 109.8(9) . .
C12 C8 C9 111.9(9) . .
C11 C8 C9 110.5(9) . .
C12 C8 C7 109.8(9) . .
C11 C8 C7 111.7(8) . .
C9 C8 C7 103.1(8) . .
C8 C9 C10 106.2(9) . .
N2 C10 C9 101.7(8) . .
F5 C12 F6 107.9(11) . .
F5 C12 F4 107.5(11) . .
F6 C12 F4 107.6(10) . .
F5 C12 C8 111.6(10) . .
F6 C12 C8 111.6(10) . .
F4 C12 C8 110.5(10) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
K1 O7A 2.878(11) .
K1 O7A 2.878(11) 2
K1 O6A 2.884(10) .
K1 O6A 2.884(10) 2
K1 O2A 2.883(9) .
K1 O2A 2.883(9) 2
K1 O6B 2.922(17) 2_545
K1 O6B 2.922(17) 1_545
K1 O5B 2.950(16) .
K1 O5B 2.950(16) 2
K1 O3B 2.96(3) .
K1 O3B 2.96(3) 2
CL1 O3B 1.34(3) .
CL1 O1A 1.377(11) .
CL1 O1B 1.41(4) .
CL1 O2B 1.42(3) .
CL1 O4A 1.435(11) .
CL1 O3A 1.455(8) .
CL1 O2A 1.473(8) .
CL1 O4B 1.53(4) .
CL2 O5B 1.412(11) .
CL2 O5B 1.412(11) 2
CL2 O5A 1.425(7) 2
CL2 O5A 1.425(7) .
CL2 O6B 1.441(11) .
CL2 O6B 1.441(11) 2
CL2 O6A 1.449(7) .
CL2 O6A 1.449(7) 2
CL2 K1 3.544(4) 1_565
O5Ac K1 2.970(10) 1_565
O6Bd K1 2.922(17) 1_565
CL3Ae O7A 1.282(12) .
CL3Ae O10A 1.402(12) .
CL3Ae O8A 1.464(13) .
CL3Ae O9A 1.480(14) .
CL3Bf O10B 1.35(3) .
CL3Bf O8B 1.43(2) .
CL3Bf O9B 1.45(2) .
CL3Bf O7B 1.47(2) .
F4 C12 1.362(14) .
F5 C12 1.327(17) .
F6 C12 1.329(13) .
F1 C6 1.347(19) .
F2 C6 1.35(2) .
F3 C6 1.355(16) .
N1 C4 1.477(14) .
N1 C1 1.507(13) .
N2 C10 1.466(13) .
N2 C7 1.500(14) .
C1 C3 1.544(13) .
C2 C4 1.541(16) .
C2 C3 1.551(16) .
C3 C6 1.452(18) .
C3 C5 1.529(15) .
C7 C8 1.556(12) .
C8 C12 1.506(15) .
C8 C11 1.509(13) .
C8 C9 1.531(16) .
C9 C10 1.546(16) .
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
N2 H3N O11Ae 0.91 1.96 2.834(13) 160.6 .
N1 H1N O3Aa_$1 0.91 2.20 3.024(13) 149.7 3_565
N1 H2N O11Ae_$2 0.91 1.96 2.842(14) 163.6 4
N2 H4N O2Aa_$3 0.91 2.24 3.028(14) 144.6 1_565
N2 H4N O2Bb_$3 0.91 1.98 2.83(3) 154.7 1_565
N2 H4N O5Ac_$4 0.91 2.32 2.991(12) 130.6 2
