#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/07/2230752.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_2230752
loop_
_publ_author_name
'Li, Gong-Chun'
'Wu, Chang-Zeng'
'Guo, Li-Li'
'Yang, Feng-Ling'
_publ_section_title
;
 Ethyl
 6-(4-fluorophenyl)-4-hydroxy-2-oxo-4-trifluoromethyl-1,3-diazinane-5-carboxylate
 monohydrate
;
_journal_coeditor_code           JH2293
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1704
_journal_page_last               o1705
_journal_paper_doi               10.1107/S1600536811021866
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C14 H14 F4 N2 O4, H2 O1'
_chemical_formula_moiety         'C14 H14 F4 N2 O4, H2 O1'
_chemical_formula_sum            'C14 H16 F4 N2 O5'
_chemical_formula_weight         368.29
_chemical_name_systematic
;
Ethyl 6-(4-fluorophenyl)-4-hydroxy-2-oxo-4-trifluoromethyl-
1,3-diazinane-5-carboxylate monohydrate
;
_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
_cell_angle_alpha                98.463(7)
_cell_angle_beta                 103.642(8)
_cell_angle_gamma                104.400(9)
_cell_formula_units_Z            4
_cell_length_a                   10.0196(9)
_cell_length_b                   12.1718(12)
_cell_length_c                   14.3037(14)
_cell_measurement_reflns_used    5664
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      27.9
_cell_measurement_theta_min      1.5
_cell_volume                     1602.2(3)
_computing_cell_refinement       'CrystalClear (Rigaku, 2009)'
_computing_data_collection       'CrystalClear (Rigaku, 2009)'
_computing_data_reduction        'CrystalClear (Rigaku, 2009)'
_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      113(2)
_diffrn_detector_area_resol_mean 14.63
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Rigaku Saturn CCD area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  multilayer
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0410
_diffrn_reflns_av_sigmaI/netI    0.0652
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            20692
_diffrn_reflns_theta_full        27.89
_diffrn_reflns_theta_max         27.89
_diffrn_reflns_theta_min         1.50
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.144
_exptl_absorpt_correction_T_max  0.9801
_exptl_absorpt_correction_T_min  0.9717
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrystalClear; Rigaku, 2009)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.527
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.345
_refine_diff_density_min         -0.189
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.870
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     493
_refine_ls_number_reflns         7612
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.870
_refine_ls_R_factor_all          0.0464
_refine_ls_R_factor_gt           0.0313
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0267P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0692
_refine_ls_wR_factor_ref         0.0721
_reflns_number_gt                4575
_reflns_number_total             7612
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jh2293.cif
_cod_data_source_block           I
_cod_database_code               2230752
_cod_database_fobs_code          2230752
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_symmetry_multiplicity
_atom_site_disorder_assembly
_atom_site_disorder_group
F F1 0.21735(8) 0.30976(7) 0.47711(6) 0.0278(2) Uani d . 1 1 . .
F F2 0.44636(9) 0.33996(7) 0.51405(6) 0.0313(2) Uani d . 1 1 . .
F F3 0.30625(9) 0.19817(7) 0.39477(6) 0.0288(2) Uani d . 1 1 . .
F F4 0.49822(9) 0.38466(7) 1.13399(6) 0.0355(2) Uani d . 1 1 . .
F F5 -0.11880(8) 0.62729(6) 0.98946(6) 0.02501(19) Uani d . 1 1 . .
F F6 0.01160(8) 0.72196(7) 1.13589(6) 0.02698(19) Uani d . 1 1 . .
F F7 0.09316(8) 0.61081(6) 1.04636(6) 0.02592(19) Uani d . 1 1 . .
F F8 0.28213(9) 0.78195(7) 0.49828(6) 0.0356(2) Uani d . 1 1 . .
O O1 0.57514(10) 0.02599(8) 0.62488(6) 0.0205(2) Uani d . 1 1 . .
O O2 0.16764(10) 0.09767(8) 0.52602(7) 0.0212(2) Uani d . 1 1 . .
H H2 0.1553(16) 0.0484(13) 0.4701(12) 0.041(5) Uiso d . 1 1 . .
O O3 0.10031(10) 0.25206(8) 0.67210(7) 0.0236(2) Uani d . 1 1 . .
O O4 0.27857(9) 0.41634(7) 0.69581(7) 0.0218(2) Uani d . 1 1 . .
O O5 0.44555(9) 0.97089(7) 1.10542(6) 0.0191(2) Uani d . 1 1 . .
O O6 -0.00739(10) 0.86354(8) 0.99826(7) 0.0189(2) Uani d . 1 1 . .
H H6 0.0185(16) 0.9111(13) 1.0575(12) 0.039(5) Uiso d . 1 1 . .
O O7 -0.13754(10) 0.74745(8) 0.79365(7) 0.0226(2) Uani d . 1 1 . .
O O8 -0.07876(9) 0.58103(7) 0.79232(6) 0.0209(2) Uani d . 1 1 . .
N N1 0.41809(12) 0.11768(10) 0.55571(8) 0.0196(3) Uani d . 1 1 . .
N N2 0.45729(12) 0.10551(10) 0.71961(8) 0.0191(3) Uani d . 1 1 . .
N N3 0.22350(12) 0.84435(9) 1.06802(8) 0.0173(2) Uani d . 1 1 . .
N N4 0.31320(12) 0.91025(10) 0.94499(8) 0.0184(3) Uani d . 1 1 . .
C C1 0.48618(14) 0.07974(11) 0.63376(9) 0.0175(3) Uani d . 1 1 . .
C C2 0.30765(14) 0.17404(11) 0.55694(9) 0.0172(3) Uani d . 1 1 . .
C C3 0.32023(15) 0.25634(12) 0.48542(10) 0.0211(3) Uani d . 1 1 . .
C C4 0.33613(14) 0.24284(11) 0.66264(9) 0.0163(3) Uani d . 1 1 . .
H H4 0.4306 0.3044 0.6806 0.020 Uiso calc R 1 1 . .
C C5 0.22216(14) 0.30121(11) 0.67569(9) 0.0177(3) Uani d . 1 1 . .
C C6 0.18167(15) 0.48463(12) 0.71134(10) 0.0256(3) Uani d . 1 1 . .
H H6A 0.2381 0.5624 0.7530 0.031 Uiso calc R 1 1 . .
H H6B 0.1156 0.4457 0.7462 0.031 Uiso calc R 1 1 . .
C C7 0.09575(15) 0.49743(12) 0.61357(10) 0.0292(4) Uani d . 1 1 . .
H H7A 0.1613 0.5278 0.5760 0.044 Uiso calc R 1 1 . .
H H7B 0.0402 0.5513 0.6251 0.044 Uiso calc R 1 1 . .
H H7C 0.0301 0.4214 0.5762 0.044 Uiso calc R 1 1 . .
C C8 0.34703(14) 0.16004(11) 0.73406(9) 0.0167(3) Uani d . 1 1 . .
H H8 0.2527 0.0986 0.7177 0.020 Uiso calc R 1 1 . .
C C9 0.38729(14) 0.22261(11) 0.84106(9) 0.0169(3) Uani d . 1 1 . .
C C10 0.30035(14) 0.18702(11) 0.90023(10) 0.0198(3) Uani d . 1 1 . .
H H10 0.2135 0.1254 0.8723 0.024 Uiso calc R 1 1 . .
C C11 0.33834(15) 0.23995(12) 0.99955(10) 0.0232(3) Uani d . 1 1 . .
H H11 0.2798 0.2143 1.0402 0.028 Uiso calc R 1 1 . .
C C12 0.46237(15) 0.32993(12) 1.03707(10) 0.0235(3) Uani d . 1 1 . .
C C13 0.55181(15) 0.36883(12) 0.98175(10) 0.0259(3) Uani d . 1 1 . .
H H13 0.6374 0.4316 1.0101 0.031 Uiso calc R 1 1 . .
C C14 0.51319(15) 0.31362(12) 0.88317(10) 0.0231(3) Uani d . 1 1 . .
H H14 0.5740 0.3385 0.8437 0.028 Uiso calc R 1 1 . .
C C15 0.33267(14) 0.91286(11) 1.04127(9) 0.0164(3) Uani d . 1 1 . .
C C16 0.08059(13) 0.79019(11) 1.00238(9) 0.0157(3) Uani d . 1 1 . .
C C17 0.01571(14) 0.68607(11) 1.04325(10) 0.0196(3) Uani d . 1 1 . .
C C18 0.09283(13) 0.75018(11) 0.89773(9) 0.0157(3) Uani d . 1 1 . .
H H18 0.1481 0.6921 0.8994 0.019 Uiso calc R 1 1 . .
C C19 -0.05367(14) 0.69559(11) 0.82313(9) 0.0179(3) Uani d . 1 1 . .
C C20 -0.21972(15) 0.51967(11) 0.72276(10) 0.0263(3) Uani d . 1 1 . .
H H20A -0.2292 0.5474 0.6605 0.032 Uiso calc R 1 1 . .
H H20B -0.2968 0.5335 0.7510 0.032 Uiso calc R 1 1 . .
C C21 -0.23104(15) 0.39215(11) 0.70373(10) 0.0267(3) Uani d . 1 1 . .
H H21A -0.1517 0.3801 0.6785 0.040 Uiso calc R 1 1 . .
H H21B -0.3228 0.3484 0.6550 0.040 Uiso calc R 1 1 . .
H H21C -0.2259 0.3650 0.7653 0.040 Uiso calc R 1 1 . .
C C22 0.17640(13) 0.85802(11) 0.86849(9) 0.0160(3) Uani d . 1 1 . .
H H22 0.1201 0.9153 0.8673 0.019 Uiso calc R 1 1 . .
C C23 0.20333(14) 0.83296(10) 0.76879(9) 0.0162(3) Uani d . 1 1 . .
C C24 0.10992(14) 0.84699(11) 0.68548(9) 0.0197(3) Uani d . 1 1 . .
H H24 0.0276 0.8695 0.6915 0.024 Uiso calc R 1 1 . .
C C25 0.13467(15) 0.82869(11) 0.59370(10) 0.0218(3) Uani d . 1 1 . .
H H25 0.0699 0.8373 0.5369 0.026 Uiso calc R 1 1 . .
C C26 0.25512(15) 0.79791(11) 0.58763(10) 0.0233(3) Uani d . 1 1 . .
C C27 0.35117(15) 0.78274(11) 0.66745(10) 0.0225(3) Uani d . 1 1 . .
H H27 0.4336 0.7610 0.6604 0.027 Uiso calc R 1 1 . .
C C28 0.32418(14) 0.80009(11) 0.75858(10) 0.0198(3) Uani d . 1 1 . .
H H28 0.3886 0.7895 0.8146 0.024 Uiso calc R 1 1 . .
O O9 0.13823(13) 0.94116(9) 0.35763(7) 0.0243(2) Uani d . 1 1 . .
O O10 0.90924(12) 0.99386(10) 0.82314(8) 0.0282(3) Uani d . 1 1 . .
H H1A 0.4218(15) 0.0862(12) 0.5014(10) 0.027(4) Uiso d . 1 1 . .
H H2A 0.4935(15) 0.0714(12) 0.7678(11) 0.035(4) Uiso d . 1 1 . .
H H3A 0.2281(16) 0.8644(13) 1.1265(11) 0.033(5) Uiso d . 1 1 . .
H H4A 0.3906(15) 0.9527(12) 0.9307(10) 0.032(4) Uiso d . 1 1 . .
H H9A 0.065(2) 0.8778(17) 0.3556(14) 0.081(7) Uiso d . 1 1 . .
H H9B 0.215(2) 0.9295(17) 0.3632(14) 0.074(8) Uiso d . 1 1 . .
H H10A 0.8938(18) 1.0100(14) 0.7657(13) 0.049(5) Uiso d . 1 1 . .
H H10B 0.883(2) 0.9233(18) 0.8184(14) 0.080(8) Uiso d . 1 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'
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
C2 O2 H2 . . 109.7(10) ?
C5 O4 C6 . . 116.13(10) ?
C16 O6 H6 . . 107.7(10) ?
C19 O8 C20 . . 115.41(10) ?
C1 N1 C2 . . 124.52(12) ?
C1 N1 H1A . . 114.5(10) ?
C2 N1 H1A . . 117.6(10) ?
C1 N2 C8 . . 124.97(11) ?
C1 N2 H2A . . 116.4(9) ?
C8 N2 H2A . . 117.0(9) ?
C15 N3 C16 . . 123.46(11) ?
C15 N3 H3A . . 113.1(11) ?
C16 N3 H3A . . 115.5(11) ?
C15 N4 C22 . . 125.04(11) ?
C15 N4 H4A . . 113.9(9) ?
C22 N4 H4A . . 120.5(9) ?
O1 C1 N2 . . 121.75(12) ?
O1 C1 N1 . . 120.47(12) ?
N2 C1 N1 . . 117.75(12) ?
O2 C2 N1 . . 114.18(11) ?
O2 C2 C3 . . 108.30(10) ?
N1 C2 C3 . . 106.15(11) ?
O2 C2 C4 . . 108.86(10) ?
N1 C2 C4 . . 108.53(10) ?
C3 C2 C4 . . 110.82(11) ?
F2 C3 F3 . . 107.29(11) ?
F2 C3 F1 . . 106.81(11) ?
F3 C3 F1 . . 107.09(10) ?
F2 C3 C2 . . 112.82(11) ?
F3 C3 C2 . . 111.21(11) ?
F1 C3 C2 . . 111.32(11) ?
C5 C4 C2 . . 114.01(10) ?
C5 C4 C8 . . 109.05(11) ?
C2 C4 C8 . . 108.95(10) ?
C5 C4 H4 . . 108.2 ?
C2 C4 H4 . . 108.2 ?
C8 C4 H4 . . 108.2 ?
O3 C5 O4 . . 124.46(12) ?
O3 C5 C4 . . 125.69(12) ?
O4 C5 C4 . . 109.81(11) ?
O4 C6 C7 . . 110.18(11) ?
O4 C6 H6A . . 109.6 ?
C7 C6 H6A . . 109.6 ?
O4 C6 H6B . . 109.6 ?
C7 C6 H6B . . 109.6 ?
H6A C6 H6B . . 108.1 ?
C6 C7 H7A . . 109.5 ?
C6 C7 H7B . . 109.5 ?
H7A C7 H7B . . 109.5 ?
C6 C7 H7C . . 109.5 ?
H7A C7 H7C . . 109.5 ?
H7B C7 H7C . . 109.5 ?
N2 C8 C9 . . 109.11(10) ?
N2 C8 C4 . . 107.61(10) ?
C9 C8 C4 . . 112.55(10) ?
N2 C8 H8 . . 109.2 ?
C9 C8 H8 . . 109.2 ?
C4 C8 H8 . . 109.2 ?
C10 C9 C14 . . 118.47(13) ?
C10 C9 C8 . . 120.19(12) ?
C14 C9 C8 . . 121.31(12) ?
C9 C10 C11 . . 121.14(13) ?
C9 C10 H10 . . 119.4 ?
C11 C10 H10 . . 119.4 ?
C12 C11 C10 . . 118.08(13) ?
C12 C11 H11 . . 121.0 ?
C10 C11 H11 . . 121.0 ?
C11 C12 F4 . . 118.40(13) ?
C11 C12 C13 . . 123.12(13) ?
F4 C12 C13 . . 118.48(13) ?
C12 C13 C14 . . 117.91(13) ?
C12 C13 H13 . . 121.0 ?
C14 C13 H13 . . 121.0 ?
C13 C14 C9 . . 121.27(13) ?
C13 C14 H14 . . 119.4 ?
C9 C14 H14 . . 119.4 ?
O5 C15 N4 . . 123.03(12) ?
O5 C15 N3 . . 119.63(12) ?
N4 C15 N3 . . 117.30(12) ?
O6 C16 N3 . . 113.49(10) ?
O6 C16 C17 . . 109.05(10) ?
N3 C16 C17 . . 105.57(10) ?
O6 C16 C18 . . 109.01(10) ?
N3 C16 C18 . . 108.46(10) ?
C17 C16 C18 . . 111.26(11) ?
F5 C17 F7 . . 107.47(10) ?
F5 C17 F6 . . 107.27(10) ?
F7 C17 F6 . . 107.20(10) ?
F5 C17 C16 . . 112.27(11) ?
F7 C17 C16 . . 111.87(11) ?
F6 C17 C16 . . 110.49(11) ?
C19 C18 C22 . . 110.15(10) ?
C19 C18 C16 . . 111.83(10) ?
C22 C18 C16 . . 107.50(10) ?
C19 C18 H18 . . 109.1 ?
C22 C18 H18 . . 109.1 ?
C16 C18 H18 . . 109.1 ?
O7 C19 O8 . . 123.52(12) ?
O7 C19 C18 . . 125.21(12) ?
O8 C19 C18 . . 111.27(11) ?
O8 C20 C21 . . 107.16(11) ?
O8 C20 H20A . . 110.3 ?
C21 C20 H20A . . 110.3 ?
O8 C20 H20B . . 110.3 ?
C21 C20 H20B . . 110.3 ?
H20A C20 H20B . . 108.5 ?
C20 C21 H21A . . 109.5 ?
C20 C21 H21B . . 109.5 ?
H21A C21 H21B . . 109.5 ?
C20 C21 H21C . . 109.5 ?
H21A C21 H21C . . 109.5 ?
H21B C21 H21C . . 109.5 ?
N4 C22 C23 . . 109.79(11) ?
N4 C22 C18 . . 107.87(10) ?
C23 C22 C18 . . 114.33(10) ?
N4 C22 H22 . . 108.2 ?
C23 C22 H22 . . 108.2 ?
C18 C22 H22 . . 108.2 ?
C24 C23 C28 . . 118.56(12) ?
C24 C23 C22 . . 120.04(11) ?
C28 C23 C22 . . 121.35(11) ?
C25 C24 C23 . . 121.33(12) ?
C25 C24 H24 . . 119.3 ?
C23 C24 H24 . . 119.3 ?
C26 C25 C24 . . 117.96(12) ?
C26 C25 H25 . . 121.0 ?
C24 C25 H25 . . 121.0 ?
F8 C26 C25 . . 118.52(12) ?
F8 C26 C27 . . 118.24(12) ?
C25 C26 C27 . . 123.24(13) ?
C26 C27 C28 . . 118.16(13) ?
C26 C27 H27 . . 120.9 ?
C28 C27 H27 . . 120.9 ?
C27 C28 C23 . . 120.75(12) ?
C27 C28 H28 . . 119.6 ?
C23 C28 H28 . . 119.6 ?
H9A O9 H9B . . 114.7(18) ?
H10A O10 H10B . . 110.6(17) ?
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
F1 C3 . 1.3408(15) ?
F2 C3 . 1.3395(15) ?
F3 C3 . 1.3405(15) ?
F4 C12 . 1.3671(15) ?
F5 C17 . 1.3378(15) ?
F6 C17 . 1.3464(14) ?
F7 C17 . 1.3388(14) ?
F8 C26 . 1.3641(14) ?
O1 C1 . 1.2480(15) ?
O2 C2 . 1.4019(15) ?
O2 H2 . 0.889(15) ?
O3 C5 . 1.2039(15) ?
O4 C5 . 1.3328(15) ?
O4 C6 . 1.4600(15) ?
O5 C15 . 1.2419(15) ?
O6 C16 . 1.4001(15) ?
O6 H6 . 0.893(16) ?
O7 C19 . 1.2072(15) ?
O8 C19 . 1.3395(15) ?
O8 C20 . 1.4615(16) ?
N1 C1 . 1.3690(16) ?
N1 C2 . 1.4418(16) ?
N1 H1A . 0.828(14) ?
N2 C1 . 1.3377(16) ?
N2 C8 . 1.4614(16) ?
N2 H2A . 0.906(14) ?
N3 C15 . 1.3697(16) ?
N3 C16 . 1.4424(17) ?
N3 H3A . 0.823(14) ?
N4 C15 . 1.3390(16) ?
N4 C22 . 1.4610(16) ?
N4 H4A . 0.904(14) ?
C2 C3 . 1.5380(18) ?
C2 C4 . 1.5405(17) ?
C4 C5 . 1.5194(17) ?
C4 C8 . 1.5416(17) ?
C4 H4 . 1.0000 ?
C6 C7 . 1.5114(18) ?
C6 H6A . 0.9900 ?
C6 H6B . 0.9900 ?
C7 H7A . 0.9800 ?
C7 H7B . 0.9800 ?
C7 H7C . 0.9800 ?
C8 C9 . 1.5159(17) ?
C8 H8 . 1.0000 ?
C9 C10 . 1.3896(17) ?
C9 C14 . 1.3897(18) ?
C10 C11 . 1.3898(18) ?
C10 H10 . 0.9500 ?
C11 C12 . 1.3666(19) ?
C11 H11 . 0.9500 ?
C12 C13 . 1.374(2) ?
C13 C14 . 1.3871(18) ?
C13 H13 . 0.9500 ?
C14 H14 . 0.9500 ?
C16 C17 . 1.5356(18) ?
C16 C18 . 1.5474(17) ?
C18 C19 . 1.5173(18) ?
C18 C22 . 1.5424(17) ?
C18 H18 . 1.0000 ?
C20 C21 . 1.5066(18) ?
C20 H20A . 0.9900 ?
C20 H20B . 0.9900 ?
C21 H21A . 0.9800 ?
C21 H21B . 0.9800 ?
C21 H21C . 0.9800 ?
C22 C23 . 1.5146(17) ?
C22 H22 . 1.0000 ?
C23 C24 . 1.3923(17) ?
C23 C28 . 1.3981(18) ?
C24 C25 . 1.3890(17) ?
C24 H24 . 0.9500 ?
C25 C26 . 1.3671(19) ?
C25 H25 . 0.9500 ?
C26 C27 . 1.3769(18) ?
C27 C28 . 1.3894(18) ?
C27 H27 . 0.9500 ?
C28 H28 . 0.9500 ?
O9 H9A . 0.91(2) ?
O9 H9B . 0.80(2) ?
O10 H10A . 0.861(17) ?
O10 H10B . 0.82(2) ?
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
O2 H2 O9 1_545 0.889(15) 1.860(16) 2.7482(14) 176.2(15)
O9 H9A O3 2_566 0.91(2) 1.90(2) 2.8026(15) 169.8(18)
O6 H6 O10 2_677 0.893(16) 1.788(16) 2.6770(14) 173.5(15)
N3 H3A O10 2_677 0.823(14) 2.583(15) 3.0737(16) 119.6(12)
N4 H4A O5 2_677 0.904(14) 1.900(15) 2.8010(14) 174.8(13)
N1 H1A O1 2_656 0.828(14) 2.109(14) 2.9235(15) 167.9(13)
N2 H2A O5 2_667 0.906(14) 1.958(15) 2.8395(14) 163.8(13)
O9 H9B O1 2_666 0.80(2) 2.00(2) 2.7443(15) 155(2)
O10 H10A O9 2_676 0.861(17) 1.925(17) 2.7833(15) 175.4(16)
O10 H10B O7 1_655 0.82(2) 2.07(2) 2.8685(14) 166(2)
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
C8 N2 C1 O1 . . . . -175.03(12) ?
C8 N2 C1 N1 . . . . 7.05(19) ?
C2 N1 C1 O1 . . . . 176.03(12) ?
C2 N1 C1 N2 . . . . -6.03(19) ?
C1 N1 C2 O2 . . . . -90.65(15) ?
C1 N1 C2 C3 . . . . 150.12(12) ?
C1 N1 C2 C4 . . . . 30.96(17) ?
O2 C2 C3 F2 . . . . 174.10(10) ?
N1 C2 C3 F2 . . . . -62.89(14) ?
C4 C2 C3 F2 . . . . 54.76(14) ?
O2 C2 C3 F3 . . . . -65.29(13) ?
N1 C2 C3 F3 . . . . 57.72(14) ?
C4 C2 C3 F3 . . . . 175.37(10) ?
O2 C2 C3 F1 . . . . 54.03(14) ?
N1 C2 C3 F1 . . . . 177.05(11) ?
C4 C2 C3 F1 . . . . -65.30(14) ?
O2 C2 C4 C5 . . . . -51.86(14) ?
N1 C2 C4 C5 . . . . -176.67(10) ?
C3 C2 C4 C5 . . . . 67.14(14) ?
O2 C2 C4 C8 . . . . 70.19(12) ?
N1 C2 C4 C8 . . . . -54.63(14) ?
C3 C2 C4 C8 . . . . -170.82(11) ?
C6 O4 C5 O3 . . . . -1.83(18) ?
C6 O4 C5 C4 . . . . -179.41(10) ?
C2 C4 C5 O3 . . . . 69.04(17) ?
C8 C4 C5 O3 . . . . -52.95(17) ?
C2 C4 C5 O4 . . . . -113.42(12) ?
C8 C4 C5 O4 . . . . 124.58(11) ?
C5 O4 C6 C7 . . . . -84.19(14) ?
C1 N2 C8 C9 . . . . -155.05(12) ?
C1 N2 C8 C4 . . . . -32.65(17) ?
C5 C4 C8 N2 . . . . 180.00(10) ?
C2 C4 C8 N2 . . . . 55.00(13) ?
C5 C4 C8 C9 . . . . -59.74(14) ?
C2 C4 C8 C9 . . . . 175.25(11) ?
N2 C8 C9 C10 . . . . -116.25(13) ?
C4 C8 C9 C10 . . . . 124.37(12) ?
N2 C8 C9 C14 . . . . 61.58(15) ?
C4 C8 C9 C14 . . . . -57.80(15) ?
C14 C9 C10 C11 . . . . -0.64(18) ?
C8 C9 C10 C11 . . . . 177.25(11) ?
C9 C10 C11 C12 . . . . 1.40(19) ?
C10 C11 C12 F4 . . . . 178.09(11) ?
C10 C11 C12 C13 . . . . -1.1(2) ?
C11 C12 C13 C14 . . . . 0.1(2) ?
F4 C12 C13 C14 . . . . -179.12(11) ?
C12 C13 C14 C9 . . . . 0.7(2) ?
C10 C9 C14 C13 . . . . -0.43(19) ?
C8 C9 C14 C13 . . . . -178.30(12) ?
C22 N4 C15 O5 . . . . -170.31(12) ?
C22 N4 C15 N3 . . . . 12.12(18) ?
C16 N3 C15 O5 . . . . 168.82(11) ?
C16 N3 C15 N4 . . . . -13.53(18) ?
C15 N3 C16 O6 . . . . -83.84(15) ?
C15 N3 C16 C17 . . . . 156.78(12) ?
C15 N3 C16 C18 . . . . 37.46(16) ?
O6 C16 C17 F5 . . . . 57.31(14) ?
N3 C16 C17 F5 . . . . 179.58(10) ?
C18 C16 C17 F5 . . . . -62.96(14) ?
O6 C16 C17 F7 . . . . 178.24(10) ?
N3 C16 C17 F7 . . . . -59.49(13) ?
C18 C16 C17 F7 . . . . 57.97(14) ?
O6 C16 C17 F6 . . . . -62.40(13) ?
N3 C16 C17 F6 . . . . 59.87(13) ?
C18 C16 C17 F6 . . . . 177.33(10) ?
O6 C16 C18 C19 . . . . -54.09(13) ?
N3 C16 C18 C19 . . . . -178.11(10) ?
C17 C16 C18 C19 . . . . 66.20(14) ?
O6 C16 C18 C22 . . . . 66.94(13) ?
N3 C16 C18 C22 . . . . -57.08(13) ?
C17 C16 C18 C22 . . . . -172.77(10) ?
C20 O8 C19 O7 . . . . -2.87(18) ?
C20 O8 C19 C18 . . . . 177.89(10) ?
C22 C18 C19 O7 . . . . -49.13(17) ?
C16 C18 C19 O7 . . . . 70.36(16) ?
C22 C18 C19 O8 . . . . 130.10(11) ?
C16 C18 C19 O8 . . . . -110.42(12) ?
C19 O8 C20 C21 . . . . -175.59(11) ?
C15 N4 C22 C23 . . . . -159.94(12) ?
C15 N4 C22 C18 . . . . -34.77(16) ?
C19 C18 C22 N4 . . . . 177.29(10) ?
C16 C18 C22 N4 . . . . 55.21(13) ?
C19 C18 C22 C23 . . . . -60.28(14) ?
C16 C18 C22 C23 . . . . 177.64(10) ?
N4 C22 C23 C24 . . . . -143.56(12) ?
C18 C22 C23 C24 . . . . 95.07(14) ?
N4 C22 C23 C28 . . . . 33.85(16) ?
C18 C22 C23 C28 . . . . -87.53(15) ?
C28 C23 C24 C25 . . . . 0.19(19) ?
C22 C23 C24 C25 . . . . 177.67(12) ?
C23 C24 C25 C26 . . . . -0.9(2) ?
C24 C25 C26 F8 . . . . -178.72(11) ?
C24 C25 C26 C27 . . . . 1.0(2) ?
F8 C26 C27 C28 . . . . 179.41(11) ?
C25 C26 C27 C28 . . . . -0.3(2) ?
C26 C27 C28 C23 . . . . -0.5(2) ?
C24 C23 C28 C27 . . . . 0.53(19) ?
C22 C23 C28 C27 . . . . -176.91(12) ?
