#------------------------------------------------------------------------------
#$Date: 2016-02-16 03:10:39 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176453 $
#$URL: svn://www.crystallography.net/cod/cif/7/21/56/7215694.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_7215694
loop_
_publ_author_name
'Singh, Shiv Shankar'
'Thakur, Tejender S.'
_publ_section_title
;
 New crystalline salt forms of levofloxacin: conformational analysis and
 attempts towards the crystal structure prediction of the anhydrous form
;
_journal_issue                   20
_journal_name_full               CrystEngComm
_journal_page_first              4215
_journal_paper_doi               10.1039/c4ce00263f
_journal_volume                  16
_journal_year                    2014
_chemical_absolute_configuration unk
_chemical_compound_source        'see text'
_chemical_formula_moiety         'C18 H21 F N3 O4, 0.5(C4 O4), 2(O)'
_chemical_formula_sum            'C20 H21 F N3 O8'
_chemical_formula_weight         450.40
_chemical_name_systematic        ?
_space_group_IT_number           5
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      5
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 110.106(17)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   17.06(2)
_cell_length_b                   6.916(7)
_cell_length_c                   19.12(2)
_cell_measurement_reflns_used    1949
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.3
_cell_measurement_theta_min      3.2
_cell_volume                     2118(4)
_computing_cell_refinement
;
CrystalClear-SM Expert 2.1 b24 (Rigaku, 2012)
;
_computing_data_collection
;
CrystalClear-SM Expert 2.1 b24 (Rigaku, 2012)
;
_computing_data_reduction
;
CrystalClear-SM Expert 2.1 b24 (Rigaku, 2012)
;
_computing_publication_material  'PLATON (Spek, 2003)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_details
;
scan:
    Number of images: 200
               Slice: -30.0000 - 70.0000
         Image width: 0.5000
            Exp time: 25.0000
       Rotation axis: Omega
               Omega: 0.0000
               Kappa: 60.0000
                 Phi: 0.0000
                 XTD: 45.1428
              2theta: -19.6855
scan:
    Number of images: 200
               Slice: -30.0000 - 70.0000
         Image width: 0.5000
            Exp time: 25.0000
       Rotation axis: Omega
               Omega: 0.0000
               Kappa: 60.0000
                 Phi: 90.0000
                 XTD: 45.1428
              2theta: -19.6855
scan:
    Number of images: 200
               Slice: -110.0000 - -10.0000
         Image width: 0.5000
            Exp time: 25.0000
       Rotation axis: Omega
               Omega: 0.0000
               Kappa: -60.0000
                 Phi: 180.0000
                 XTD: 45.1428
              2theta: -19.6855
scan:
    Number of images: 200
               Slice: -110.0000 - -10.0000
         Image width: 0.5000
            Exp time: 25.0000
       Rotation axis: Omega
               Omega: 0.0000
               Kappa: -60.0000
                 Phi: 270.0000
                 XTD: 45.1428
              2theta: -19.6855

;
_diffrn_measurement_device
;
AFC12 (Right): Kappa 3 circle
;
_diffrn_measurement_device_type
;
Rigaku Saturn724+ (4x4 bin mode)
;
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support Fiber
_diffrn_orient_matrix_type       XPlain
_diffrn_orient_matrix_UB_11      0.001900
_diffrn_orient_matrix_UB_12      -0.054424
_diffrn_orient_matrix_UB_13      0.011742
_diffrn_orient_matrix_UB_21      -0.144516
_diffrn_orient_matrix_UB_22      -0.004754
_diffrn_orient_matrix_UB_23      0.001351
_diffrn_orient_matrix_UB_31      0.000603
_diffrn_orient_matrix_UB_32      -0.033332
_diffrn_orient_matrix_UB_33      -0.052778
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0602
_diffrn_reflns_av_sigmaI/netI    0.0936
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            8156
_diffrn_reflns_reduction_process
;
;
_diffrn_reflns_theta_full        25.29
_diffrn_reflns_theta_max         25.29
_diffrn_reflns_theta_min         3.21
_diffrn_reflns_transf_matrix_11  0.001900
_diffrn_reflns_transf_matrix_12  -0.054424
_diffrn_reflns_transf_matrix_13  0.011742
_diffrn_reflns_transf_matrix_21  -0.144516
_diffrn_reflns_transf_matrix_22  -0.004754
_diffrn_reflns_transf_matrix_23  0.001351
_diffrn_reflns_transf_matrix_31  0.000603
_diffrn_reflns_transf_matrix_32  -0.033332
_diffrn_reflns_transf_matrix_33  -0.052778
_diffrn_source                   MicroMax003_Mo
_diffrn_source_current           0.6
_diffrn_source_power             0.0
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.116
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.377
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.413
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_description       Platelet
_exptl_crystal_F_000             940
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.030
_refine_diff_density_max         0.335
_refine_diff_density_min         -0.400
_refine_diff_density_rms         0.094
_refine_ls_abs_structure_details 'Flack H.D. (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.000
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     293
_refine_ls_number_reflns         3717
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.018
_refine_ls_R_factor_all          0.1369
_refine_ls_R_factor_gt           0.0834
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1459P)²]         where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2168
_refine_ls_wR_factor_ref         0.2733
_reflns_number_gt                1934
_reflns_number_total             3717
_reflns_shell_number_unique_all  4170
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            c4ce00263f2.cif
_cod_data_source_block           LevoSuccA293K
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/current/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 
;
_cod_original_sg_symbol_H-M      'C 2'
_cod_original_formula_sum        'C20 H21 F1 N3 O8'
_cod_database_code               7215694
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x,y,-z
3 1/2+x,1/2+y,z
4 1/2-x,1/2+y,-z
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_thermal_displace_type
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_U_iso_or_equiv
_atom_site_calc_flag
_atom_site_refinement_flags
F1 F Uani 0.04855(17) 0.1933(7) 0.10702(18) 1.000 0.0706(15) . .
O1 O Uani 0.4135(3) 0.1592(9) -0.0997(2) 1.000 0.0745(18) . .
O2 O Uani 0.2784(3) 0.1682(9) -0.1631(2) 1.000 0.0708(16) . .
O3 O Uani 0.1742(2) 0.1800(8) -0.09652(19) 1.000 0.0620(14) . .
O4 O Uani 0.33815(19) 0.1346(8) 0.23785(19) 1.000 0.0578(16) . .
N1 N Uani 0.3687(2) 0.1503(7) 0.1018(2) 1.000 0.0419(14) . .
N2 N Uani 0.1733(3) 0.1645(10) 0.2395(2) 1.000 0.0550(16) . .
N3 N Uani 0.2338(3) 0.3395(10) 0.3855(3) 1.000 0.0618(19) . .
C1 C Uani 0.3831(3) 0.1598(10) 0.0373(3) 1.000 0.0455(17) . .
C2 C Uani 0.3192(3) 0.1639(10) -0.0313(3) 1.000 0.0430(17) . .
C3 C Uani 0.2349(3) 0.1698(9) -0.0350(3) 1.000 0.0430(17) . .
C4 C Uani 0.1383(3) 0.1808(10) 0.0378(3) 1.000 0.0462(19) . .
C5 C Uani 0.1278(3) 0.1814(10) 0.1053(3) 1.000 0.0468(18) . .
C6 C Uani 0.1932(3) 0.1643(10) 0.1739(3) 1.000 0.0432(16) . .
C7 C Uani 0.2737(3) 0.1464(10) 0.1716(3) 1.000 0.0432(16) . .
C8 C Uani 0.2863(3) 0.1550(9) 0.1024(3) 1.000 0.0387(16) . .
C9 C Uani 0.2203(3) 0.1674(9) 0.0366(2) 1.000 0.0386(16) . .
C10 C Uani 0.3421(3) 0.1649(11) -0.0997(3) 1.000 0.0541(19) . .
C11 C Uani 0.4129(3) 0.0427(11) 0.2308(3) 1.000 0.055(2) . .
C12 C Uani 0.4400(3) 0.1533(11) 0.1734(3) 1.000 0.0540(19) . .
C13 C Uani 0.4668(4) 0.3587(14) 0.1974(4) 1.000 0.084(3) . .
C14 C Uani 0.2152(4) 0.0478(11) 0.3050(3) 1.000 0.062(2) . .
C15 C Uani 0.2737(3) 0.1633(13) 0.3691(3) 1.000 0.062(2) . .
C16 C Uani 0.1949(5) 0.4538(12) 0.3175(4) 1.000 0.075(3) . .
C17 C Uani 0.1325(4) 0.3346(12) 0.2569(3) 1.000 0.064(2) . .
C18 C Uani 0.2947(5) 0.4569(16) 0.4477(5) 1.000 0.106(4) . .
O5B O Uiso 0.4022(5) 0.7236(15) 0.5748(5) 0.527(17) 0.057(3) . .
O6B O Uiso 0.3925(11) 1.038(3) 0.5478(11) 0.527(17) 0.124(6) . .
C19B C Uiso 0.4314(8) 0.886(2) 0.5567(6) 0.527(17) 0.049(3) . .
C20B C Uiso 0.5084(9) 0.841(3) 0.5320(7) 0.527(17) 0.069(4) . .
O5A O Uiso 0.3805(8) 0.812(2) 0.5486(7) 0.473(17) 0.074(4) . .
O6A O Uiso 0.4117(7) 1.1038(19) 0.5902(7) 0.473(17) 0.080(4) . .
C19A C Uiso 0.4232(10) 0.992(3) 0.5695(10) 0.473(17) 0.054(4) . .
C20A C Uiso 0.5025(12) 0.965(4) 0.5327(9) 0.473(17) 0.085(6) . .
O7 O Uani 0.4973(7) 0.414(2) 0.6065(6) 1.000 0.226(6) . .
O8 O Uani 0.3609(15) 0.601(4) 0.3073(10) 1.000 0.413(16) . .
H1 H Uiso 0.43810 0.16370 0.03850 1.000 0.0550 calc R
H3 H Uiso 0.23550 0.13970 -0.15530 1.000 0.1060 calc R
H3N H Uiso 0.194(3) 0.300(8) 0.395(3) 1.000 0.037(15) . .
H4 H Uiso 0.09270 0.18890 -0.00610 1.000 0.0560 calc R
H11A H Uiso 0.40080 -0.09060 0.21510 1.000 0.0670 calc R
H11B H Uiso 0.45780 0.04360 0.27870 1.000 0.0670 calc R
H12 H Uiso 0.48700 0.08480 0.16650 1.000 0.0650 calc R
H13A H Uiso 0.42120 0.42780 0.20430 1.000 0.1260 calc R
H13B H Uiso 0.48300 0.42160 0.15970 1.000 0.1260 calc R
H13C H Uiso 0.51320 0.35690 0.24330 1.000 0.1260 calc R
H14A H Uiso 0.24670 -0.05330 0.29140 1.000 0.0740 calc R
H14B H Uiso 0.17340 -0.01400 0.32130 1.000 0.0740 calc R
H15A H Uiso 0.29240 0.08240 0.41320 1.000 0.0740 calc R
H15B H Uiso 0.32250 0.20030 0.35710 1.000 0.0740 calc R
H16A H Uiso 0.23790 0.50140 0.29940 1.000 0.0890 calc R
H16B H Uiso 0.16670 0.56460 0.32910 1.000 0.0890 calc R
H17A H Uiso 0.08730 0.29410 0.27350 1.000 0.0760 calc R
H17B H Uiso 0.10900 0.41290 0.21250 1.000 0.0760 calc R
H18A H Uiso 0.26650 0.56750 0.45820 1.000 0.1580 calc R
H18B H Uiso 0.34010 0.49910 0.43270 1.000 0.1580 calc R
H18C H Uiso 0.31590 0.37840 0.49160 1.000 0.1580 calc R
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
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 O4 C11 112.8(4) . yes
C10 O2 H3 109.00 . no
C1 N1 C8 120.4(4) . yes
C1 N1 C12 119.8(4) . yes
C8 N1 C12 119.7(4) . yes
C6 N2 C14 124.7(6) . yes
C6 N2 C17 118.9(5) . yes
C14 N2 C17 112.5(4) . yes
C15 N3 C18 111.4(6) . yes
C16 N3 C18 112.6(7) . yes
C15 N3 C16 110.8(5) . yes
C15 N3 H3N 105(4) . no
C16 N3 H3N 103(4) . no
C18 N3 H3N 114(4) . no
N1 C1 C2 122.6(5) . yes
C1 C2 C3 120.1(5) . no
C1 C2 C10 118.2(5) . no
C3 C2 C10 121.7(5) . no
C2 C3 C9 116.5(5) . no
O3 C3 C9 121.0(5) . yes
O3 C3 C2 122.5(5) . yes
C5 C4 C9 118.0(5) . no
F1 C5 C6 117.2(5) . yes
C4 C5 C6 124.3(5) . no
F1 C5 C4 118.5(5) . yes
N2 C6 C5 118.3(5) . yes
N2 C6 C7 124.8(5) . yes
C5 C6 C7 116.9(5) . no
O4 C7 C6 117.6(5) . yes
C6 C7 C8 119.6(5) . no
O4 C7 C8 122.6(5) . yes
N1 C8 C7 118.7(5) . yes
N1 C8 C9 120.0(5) . yes
C7 C8 C9 121.3(5) . no
C4 C9 C8 119.7(4) . no
C3 C9 C4 120.0(4) . no
C3 C9 C8 120.3(5) . no
O1 C10 C2 124.4(5) . yes
O2 C10 C2 115.1(5) . yes
O1 C10 O2 120.5(5) . yes
O4 C11 C12 109.5(5) . yes
N1 C12 C11 107.4(4) . yes
N1 C12 C13 111.0(6) . yes
C11 C12 C13 112.6(5) . no
N2 C14 C15 113.3(6) . yes
N3 C15 C14 112.5(5) . yes
N3 C16 C17 111.6(6) . yes
N2 C17 C16 110.3(6) . yes
N1 C1 H1 119.00 . no
C2 C1 H1 119.00 . no
C5 C4 H4 121.00 . no
C9 C4 H4 121.00 . no
O4 C11 H11A 110.00 . no
O4 C11 H11B 110.00 . no
C12 C11 H11A 110.00 . no
C12 C11 H11B 110.00 . no
H11A C11 H11B 108.00 . no
N1 C12 H12 109.00 . no
C11 C12 H12 109.00 . no
C13 C12 H12 109.00 . no
C12 C13 H13A 110.00 . no
C12 C13 H13B 109.00 . no
C12 C13 H13C 109.00 . no
H13A C13 H13B 109.00 . no
H13A C13 H13C 109.00 . no
H13B C13 H13C 109.00 . no
N2 C14 H14A 109.00 . no
N2 C14 H14B 109.00 . no
C15 C14 H14A 109.00 . no
C15 C14 H14B 109.00 . no
H14A C14 H14B 108.00 . no
N3 C15 H15A 109.00 . no
N3 C15 H15B 109.00 . no
C14 C15 H15A 109.00 . no
C14 C15 H15B 109.00 . no
H15A C15 H15B 108.00 . no
N3 C16 H16A 109.00 . no
N3 C16 H16B 109.00 . no
C17 C16 H16A 109.00 . no
C17 C16 H16B 109.00 . no
H16A C16 H16B 108.00 . no
N2 C17 H17A 110.00 . no
N2 C17 H17B 110.00 . no
C16 C17 H17A 110.00 . no
C16 C17 H17B 110.00 . no
H17A C17 H17B 108.00 . no
N3 C18 H18A 109.00 . no
N3 C18 H18B 110.00 . no
N3 C18 H18C 109.00 . no
H18A C18 H18B 110.00 . no
H18A C18 H18C 109.00 . no
H18B C18 H18C 109.00 . no
O5B C19B O6B 122.1(15) . yes
O5B C19B C20B 109.8(12) . yes
O6B C19B C20B 126.7(16) . yes
C19B C20B C20B 112.9(14) 2_656 no
O5A C19A O6A 134(2) . yes
O5A C19A C20A 100.7(15) . yes
O6A C19A C20A 125(2) . yes
C19A C20A C20A 128.6(18) 2_656 no
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
F1 C5 1.366(7) . yes
O1 C10 1.219(8) . yes
O2 C10 1.321(7) . yes
O3 C3 1.274(7) . yes
O4 C7 1.365(7) . yes
O4 C11 1.472(7) . yes
O2 H3 0.8200 . no
O5B C19B 1.322(17) . yes
O6B C19B 1.22(2) . yes
O5A C19A 1.43(2) . yes
O6A C19A 0.92(2) . yes
N1 C1 1.339(7) . yes
N1 C8 1.410(7) . yes
N1 C12 1.486(7) . yes
N2 C17 1.462(10) . yes
N2 C14 1.454(8) . yes
N2 C6 1.408(7) . yes
N3 C18 1.518(11) . yes
N3 C15 1.481(10) . yes
N3 C16 1.471(10) . yes
N3 H3N 0.81(5) . no
C1 C2 1.388(8) . no
C2 C10 1.488(8) . no
C2 C3 1.416(8) . no
C3 C9 1.473(7) . no
C4 C5 1.363(8) . no
C4 C9 1.410(8) . no
C5 C6 1.405(8) . no
C6 C7 1.395(8) . no
C7 C8 1.413(8) . no
C8 C9 1.373(7) . no
C11 C12 1.534(9) . no
C12 C13 1.514(12) . no
C14 C15 1.515(9) . no
C16 C17 1.519(11) . no
C1 H1 0.9300 . no
C4 H4 0.9300 . no
C11 H11B 0.9700 . no
C11 H11A 0.9700 . no
C12 H12 0.9800 . no
C13 H13C 0.9600 . no
C13 H13A 0.9600 . no
C13 H13B 0.9600 . no
C14 H14B 0.9700 . no
C14 H14A 0.9700 . no
C15 H15B 0.9700 . no
C15 H15A 0.9700 . no
C16 H16B 0.9700 . no
C16 H16A 0.9700 . no
C17 H17B 0.9700 . no
C17 H17A 0.9700 . no
C18 H18C 0.9600 . no
C18 H18B 0.9600 . no
C18 H18A 0.9600 . no
C19B C20B 1.57(2) . no
C20B C20B 1.157(18) 2_656 no
C19A C20A 1.74(3) . no
C20A C20A 1.22(2) 2_656 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 N2 2.698(6) . no
F1 C17 2.898(8) . no
F1 H17B 2.4500 . no
F1 H4 2.5200 2_555 no
F1 H13B 2.5600 3_445 no
O1 C1 3.259(8) 2_655 no
O1 C12 3.264(8) 2_655 no
O1 C5 3.373(10) 4_545 no
O2 O3 2.519(7) . no
O2 C7 3.414(10) 4_555 no
O2 O8 2.99(2) 4_545 no
O3 O2 2.519(7) . no
O3 C13 3.355(10) 4_545 no
O3 C8 3.363(9) 4_555 no
O4 N1 2.825(6) . no
O4 C15 3.073(7) . no
O4 C14 2.874(8) . no
O4 N2 2.831(7) . no
O5A C16 3.382(16) 4_556 no
O5A C18 3.155(17) . no
O5A N3 2.668(15) 4_556 no
O5A C18 3.176(18) 4_556 no
O5B O7 2.628(17) . no
O5B N3 2.795(11) 4_556 no
O5B C18 3.100(14) . no
O6A C16 3.115(16) 4_556 no
O6A O7 2.553(19) 1_565 no
O6A N3 3.242(15) 4_556 no
O6B O7 3.14(2) 1_565 no
O6B C18 3.27(2) 4_556 no
O6B N3 3.17(2) 4_556 no
O7 O6A 2.553(19) 1_545 no
O7 C20B 3.31(2) . no
O7 C19A 3.16(2) 1_545 no
O7 O5B 2.628(17) . no
O7 O6B 3.14(2) 1_545 no
O7 O8 2.74(3) 2_656 no
O8 O2 2.99(2) 4_555 no
O8 C16 3.08(3) . no
O8 C18 3.40(2) . no
O8 O7 2.74(3) 2_656 no
O1 H12 2.5000 2_655 no
O1 H1 2.4000 2_655 no
O1 H17B 2.6700 4_545 no
O1 H1 2.5300 . no
O2 H16A 2.7800 4_545 no
O3 H4 2.5600 . no
O3 H13A 2.7600 4_545 no
O3 H3 1.8000 . no
O3 H11A 2.7000 4_555 no
O4 H13A 2.6700 . no
O4 H15B 2.4300 . no
O4 H14A 2.5000 . no
O5A H18A 2.7100 . no
O5A H3N 1.93(6) 4_556 no
O5B H18A 2.8200 . no
O5B H17A 2.8900 4_556 no
O5B H3N 1.99(6) 4_556 no
O6A H18A 2.8700 4_556 no
O6A H16B 2.3800 4_556 no
O6A H3N 2.85(6) 4_556 no
O6A H18C 2.7800 1_565 no
O6A H11B 2.7500 2_666 no
O6B H18A 2.6800 4_556 no
O6B H16B 2.8700 4_556 no
O6B H15A 2.5700 1_565 no
O6B H18C 2.7300 1_565 no
O6B H3N 2.68(6) 4_556 no
O8 H16A 2.1600 . no
O8 H13A 2.7900 . no
O8 H18B 2.6400 . no
O8 H3 2.8200 4_555 no
N1 O4 2.825(6) . no
N2 N3 2.888(8) . no
N2 O4 2.831(7) . no
N2 F1 2.698(6) . no
N3 O5A 2.668(15) 4_546 no
N3 O6A 3.242(15) 4_546 no
N3 C19A 3.26(2) 4_546 no
N3 C19B 3.378(15) 4_546 no
N3 N2 2.888(8) . no
N3 O5B 2.795(11) 4_546 no
N3 O6B 3.17(2) 4_546 no
C1 C4 3.579(10) 4_545 no
C1 O1 3.259(8) 2_655 no
C2 C4 3.430(10) 4_545 no
C2 C9 3.542(10) 4_555 no
C2 C9 3.494(10) 4_545 no
C3 C8 3.568(10) 4_555 no
C3 C9 3.560(10) 4_545 no
C3 C9 3.528(10) 4_555 no
C4 C1 3.579(10) 4_555 no
C4 C2 3.430(10) 4_555 no
C4 C10 3.528(11) 4_555 no
C5 C10 3.390(11) 4_555 no
C5 O1 3.373(10) 4_555 no
C7 C13 3.483(11) . no
C7 O2 3.414(10) 4_545 no
C8 O3 3.363(9) 4_545 no
C8 C3 3.568(10) 4_545 no
C9 C3 3.560(10) 4_555 no
C9 C2 3.494(10) 4_555 no
C9 C2 3.542(10) 4_545 no
C9 C3 3.528(10) 4_545 no
C10 C5 3.390(11) 4_545 no
C10 C4 3.528(11) 4_545 no
C12 O1 3.264(8) 2_655 no
C13 O3 3.355(10) 4_555 no
C13 C7 3.483(11) . no
C14 O4 2.874(8) . no
C15 O4 3.073(7) . no
C16 C19A 3.43(2) 4_546 no
C16 O5A 3.382(16) 4_546 no
C16 O6A 3.115(16) 4_546 no
C16 O8 3.08(3) . no
C17 F1 2.898(8) . no
C18 O5A 3.176(18) 4_546 no
C18 O5B 3.100(14) . no
C18 O5A 3.155(17) . no
C18 O8 3.40(2) . no
C18 O6B 3.27(2) 4_546 no
C19A N3 3.26(2) 4_556 no
C19A O7 3.16(2) 1_565 no
C19A C16 3.43(2) 4_556 no
C19B N3 3.378(15) 4_556 no
C20B O7 3.31(2) . no
C1 H13B 2.9900 . no
C3 H3 2.3100 . no
C5 H17B 2.7100 . no
C7 H13A 3.0700 . no
C7 H14A 2.8400 . no
C8 H13A 3.0900 . no
C8 H11A 2.9100 . no
C17 H12 3.0300 3_455 no
C19A H16B 2.9000 4_556 no
C19A H3N 2.68(6) 4_556 no
C19A H11B 2.9400 2_666 no
C19B H3N 2.67(6) 4_556 no
H1 O1 2.5300 . no
H1 O1 2.4000 2_655 no
H1 H12 2.3600 . no
H3 C3 2.3100 . no
H3 O3 1.8000 . no
H3 O8 2.8200 4_545 no
H3N O5B 1.99(6) 4_546 no
H3N O6B 2.68(6) 4_546 no
H3N O5A 1.93(6) 4_546 no
H3N O6A 2.85(6) 4_546 no
H3N C19B 2.67(6) 4_546 no
H3N H14B 2.5500 . no
H3N H17A 2.4100 . no
H3N C19A 2.68(6) 4_546 no
H4 F1 2.5200 2_555 no
H4 O3 2.5600 . no
H11A C8 2.9100 . no
H11A O3 2.7000 4_545 no
H11B H13C 2.5500 . no
H11B O6A 2.7500 2_646 no
H11B C19A 2.9400 2_646 no
H12 H17B 2.2900 3_545 no
H12 C17 3.0300 3_545 no
H12 H1 2.3600 . no
H12 O1 2.5000 2_655 no
H13A O8 2.7900 . no
H13A C7 3.0700 . no
H13A C8 3.0900 . no
H13A O4 2.6700 . no
H13A O3 2.7600 4_555 no
H13B C1 2.9900 . no
H13B F1 2.5600 3_555 no
H13C H11B 2.5500 . no
H14A C7 2.8400 . no
H14A O4 2.5000 . no
H14B H3N 2.5500 . no
H14B H17A 2.5700 . no
H15A H18C 2.4900 . no
H15A O6B 2.5700 1_545 no
H15B H16A 2.5600 . no
H15B O4 2.4300 . no
H15B H18B 2.4800 . no
H16A O8 2.1600 . no
H16A H15B 2.5600 . no
H16A H18B 2.5500 . no
H16A O2 2.7800 4_555 no
H16B O6B 2.8700 4_546 no
H16B H18A 2.4700 . no
H16B O6A 2.3800 4_546 no
H16B C19A 2.9000 4_546 no
H17A H3N 2.4100 . no
H17A O5B 2.8900 4_546 no
H17A H14B 2.5700 . no
H17B H12 2.2900 3_455 no
H17B O1 2.6700 4_555 no
H17B F1 2.4500 . no
H17B C5 2.7100 . no
H18A O5A 2.7100 . no
H18A O6B 2.6800 4_546 no
H18A H16B 2.4700 . no
H18A O5B 2.8200 . no
H18A O6A 2.8700 4_546 no
H18B O8 2.6400 . no
H18B H15B 2.4800 . no
H18B H16A 2.5500 . no
H18C H15A 2.4900 . no
H18C O6A 2.7800 1_545 no
H18C O6B 2.7300 1_545 no
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
_geom_hbond_publ_flag
O2 H3 O3 0.8200 1.8000 2.519(7) 145.00 . yes
N3 H3N O5B 0.81(5) 1.99(6) 2.795(11) 175(3) 4_546 yes
C1 H1 O1 0.9300 2.5300 2.840(8) 100.00 . yes
C1 H1 O1 0.9300 2.4000 3.259(8) 154.00 2_655 yes
C4 H4 F1 0.9300 2.5200 3.430(7) 168.00 2_555 yes
C12 H12 O1 0.9800 2.5000 3.264(8) 134.00 2_655 yes
C14 H14A O4 0.9700 2.5000 2.874(8) 102.00 . yes
C15 H15A O6B 0.9700 2.5700 3.43(2) 148.00 1_545 yes
C15 H15B O4 0.9700 2.4300 3.073(7) 124.00 . yes
C16 H16A O8 0.9700 2.1600 3.08(3) 157.00 . yes
C17 H17B F1 0.9700 2.4500 2.898(8) 108.00 . 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
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C11 O4 C7 C6 157.6(6) . . no
C11 O4 C7 C8 -27.0(9) . . no
C7 O4 C11 C12 56.6(7) . . no
C8 N1 C1 C2 -3.6(10) . . no
C12 N1 C1 C2 -177.9(6) . . no
C1 N1 C12 C13 84.6(7) . . no
C8 N1 C12 C13 -89.8(6) . . no
C1 N1 C8 C9 0.7(9) . . no
C1 N1 C8 C7 -179.4(6) . . no
C12 N1 C8 C7 -5.2(9) . . no
C12 N1 C8 C9 175.0(6) . . no
C8 N1 C12 C11 33.8(8) . . no
C1 N1 C12 C11 -151.9(6) . . no
C6 N2 C14 C15 105.6(7) . . no
C17 N2 C6 C5 -61.2(8) . . no
C14 N2 C6 C7 -36.3(11) . . no
C14 N2 C17 C16 55.1(8) . . no
C6 N2 C17 C16 -103.6(6) . . no
C17 N2 C6 C7 119.5(7) . . no
C14 N2 C6 C5 143.0(7) . . no
C17 N2 C14 C15 -51.6(7) . . no
C15 N3 C16 C17 56.0(8) . . no
C18 N3 C16 C17 -178.4(6) . . no
C18 N3 C15 C14 -177.6(6) . . no
C16 N3 C15 C14 -51.4(8) . . no
N1 C1 C2 C3 3.8(10) . . no
N1 C1 C2 C10 -177.1(6) . . no
C1 C2 C3 C9 -1.2(9) . . no
C1 C2 C10 O2 179.8(7) . . no
C1 C2 C3 O3 177.7(6) . . no
C3 C2 C10 O2 -1.1(10) . . no
C10 C2 C3 C9 179.8(6) . . no
C1 C2 C10 O1 1.2(11) . . no
C10 C2 C3 O3 -1.4(10) . . no
C3 C2 C10 O1 -179.7(7) . . no
C2 C3 C9 C4 177.4(6) . . no
O3 C3 C9 C8 179.5(6) . . no
O3 C3 C9 C4 -1.4(9) . . no
C2 C3 C9 C8 -1.6(9) . . no
C9 C4 C5 F1 -179.7(6) . . no
C9 C4 C5 C6 -1.8(11) . . no
C5 C4 C9 C8 0.2(10) . . no
C5 C4 C9 C3 -178.9(6) . . no
F1 C5 C6 C7 178.1(6) . . no
F1 C5 C6 N2 -1.3(10) . . no
C4 C5 C6 N2 -179.2(7) . . no
C4 C5 C6 C7 0.3(11) . . no
N2 C6 C7 O4 -2.3(11) . . no
N2 C6 C7 C8 -177.8(7) . . no
C5 C6 C7 O4 178.4(6) . . no
C5 C6 C7 C8 2.9(10) . . no
C6 C7 C8 N1 175.6(6) . . no
O4 C7 C8 C9 -179.8(6) . . no
O4 C7 C8 N1 0.3(10) . . no
C6 C7 C8 C9 -4.5(10) . . no
C7 C8 C9 C3 -178.0(6) . . no
N1 C8 C9 C3 1.9(9) . . no
C7 C8 C9 C4 3.0(10) . . no
N1 C8 C9 C4 -177.2(6) . . no
O4 C11 C12 C13 64.1(6) . . no
O4 C11 C12 N1 -58.5(6) . . no
N2 C14 C15 N3 49.5(7) . . no
N3 C16 C17 N2 -57.9(8) . . no
O5B C19B C20B C20B 101.1(19) . 2_656 no
O6B C19B C20B C20B -66(3) . 2_656 no
C19B C20B C20B C19B 155.2(14) 2_656 2_656 no
