#------------------------------------------------------------------------------
#$Date: 2022-02-04 05:22:19 +0200 (Fri, 04 Feb 2022) $
#$Revision: 272550 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/40/2244034.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_2244034
loop_
_publ_author_name
'Nugraha, Yuda Prasetya'
'Sugiyama, Haruki'
'Uekusa, Hidehiro'
_publ_section_title
;
 Ciprofloxacin salt and salt co-crystal with dihydroxybenzoic acids
;
_journal_coeditor_code           DX2042
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first
;
;
_journal_paper_doi               10.1107/S2056989022001177
_journal_volume                  78
_journal_year                    2022
_chemical_formula_iupac          'C17 H19 F N3 O3 +, C7 H6 O4, Cl -, H2 O'
_chemical_formula_moiety         'C17 H19 F N3 O3 +, C7 H6 O4, Cl -, H2 O'
_chemical_formula_sum            'C24 H27 Cl F N3 O8'
_chemical_formula_weight         539.93
_chemical_name_common
;
Ciprofloxacin chloride--3,5-hydroxybenzoic acid--water (1/1/1)
;
_chemical_name_systematic
'4-(3-Carboxy-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydroquinolin-7-yl)piperazin-1-ium chloride--3,5-hydroxybenzoic acid--water (1/1/1)'
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_cell_angle_alpha                92.997(3)
_cell_angle_beta                 95.219(2)
_cell_angle_gamma                111.557(4)
_cell_formula_units_Z            1
_cell_length_a                   7.2165(2)
_cell_length_b                   8.8298(4)
_cell_length_c                   10.1184(3)
_cell_measurement_reflns_used    10041
_cell_measurement_temperature    93.15
_cell_measurement_theta_max      75.7970
_cell_measurement_theta_min      4.3570
_cell_volume                     594.60(4)
_computing_cell_refinement
;
CrysAlisPro (Rigaku OD, 2020)
;
_computing_data_collection
;
CrysAlisPro (Rigaku OD, 2020)
;
_computing_data_reduction
;
CrysAlisPro (Rigaku OD, 2020)
;
_computing_molecular_graphics
;
OLEX2 (Dolomanov et al.,  2009)
;
_computing_publication_material
;
Mercury (Macrae et al.,  2020)
;
_computing_structure_refinement
;
SHELXL2018/3 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT2018/2 (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      93.15
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0348
_diffrn_reflns_av_unetI/netI     0.0273
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            16358
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.461
_diffrn_reflns_theta_min         4.407
_diffrn_source                   'Rotating-anode X-ray tube'
_exptl_absorpt_coefficient_mu    1.995
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83862
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlisPro; Rigaku OD, 2020)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.508
_exptl_crystal_description       block
_exptl_crystal_F_000             282
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.245
_refine_diff_density_min         -0.468
_refine_ls_abs_structure_details
;
Flack x determined using 1889 quotients
[(I⁺)-(I⁻)]/[(I⁺)+(I⁻)]
(Parsons et al.,  2013)
;
_refine_ls_abs_structure_Flack   0.011(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.122
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     344
_refine_ls_number_reflns         4420
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.121
_refine_ls_R_factor_all          0.0347
_refine_ls_R_factor_gt           0.0341
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0589P)²+0.0709P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0937
_refine_ls_wR_factor_ref         0.0941
_reflns_number_gt                4323
_reflns_number_total             4420
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            dx2042sup1.cif
_cod_data_source_block           II
_cod_database_code               2244034
_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   0.605
_shelx_estimated_absorpt_t_max   0.907
loop_
_space_group_symop_operation_xyz
'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_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl Cl1 0.85144(9) 0.46863(8) 0.40663(7) 0.02533(17) Uani d 1 . .
F F1 0.4599(3) 0.5185(2) 0.98137(17) 0.0273(4) Uani d 1 . .
O O1 0.3224(3) -0.3703(3) 1.2978(2) 0.0284(5) Uani d 1 . .
O O2 0.3642(4) -0.1499(3) 1.4315(2) 0.0294(5) Uani d 1 . .
H H2 0.379572 -0.051835 1.423817 0.044 Uiso calc 1 . .
O O3 0.3972(3) 0.1143(3) 1.3272(2) 0.0280(5) Uani d 1 . .
N N1 0.2840(4) -0.1445(3) 0.9603(2) 0.0213(5) Uani d 1 . .
N N2 0.3796(4) 0.3457(3) 0.7334(2) 0.0210(5) Uani d 1 . .
N N3 0.4407(4) 0.4661(3) 0.4778(2) 0.0233(5) Uani d 1 . .
H H3A 0.412202 0.525266 0.413562 0.028 Uiso calc 1 . .
H H3B 0.528778 0.423848 0.448534 0.028 Uiso calc 1 . .
C C1 0.3370(4) -0.2274(4) 1.3126(3) 0.0249(6) Uani d 1 . .
C C2 0.3276(4) -0.1342(4) 1.1970(3) 0.0222(6) Uani d 1 . .
C C3 0.3655(4) 0.0366(4) 1.2138(3) 0.0226(6) Uani d 1 . .
C C4 0.3687(4) 0.1155(4) 1.0907(3) 0.0220(6) Uani d 1 . .
C C5 0.4158(4) 0.2850(4) 1.0937(3) 0.0227(6) Uani d 1 . .
H H5 0.444144 0.349621 1.176480 0.027 Uiso calc 1 . .
C C6 0.4203(4) 0.3556(4) 0.9773(3) 0.0214(6) Uani d 1 . .
C C7 0.3828(4) 0.2667(4) 0.8503(3) 0.0202(6) Uani d 1 . .
C C8 0.3389(4) 0.1003(4) 0.8483(3) 0.0212(6) Uani d 1 . .
H H8 0.314618 0.036841 0.765286 0.025 Uiso calc 1 . .
C C9 0.3297(4) 0.0241(4) 0.9661(3) 0.0204(6) Uani d 1 . .
C C10 0.2882(4) -0.2168(4) 1.0730(3) 0.0218(6) Uani d 1 . .
H H10 0.262685 -0.330555 1.066643 0.026 Uiso calc 1 . .
C C11 0.2568(4) -0.2397(4) 0.8324(3) 0.0219(6) Uani d 1 . .
H H11 0.381927 -0.228926 0.791979 0.026 Uiso calc 1 . .
C C12 0.0740(5) -0.2667(4) 0.7366(3) 0.0257(6) Uani d 1 . .
H H12A 0.087678 -0.270948 0.640183 0.031 Uiso calc 1 . .
H H12B -0.021768 -0.217677 0.763308 0.031 Uiso calc 1 . .
C C13 0.0926(5) -0.4047(4) 0.8124(3) 0.0259(6) Uani d 1 . .
H H13A 0.007825 -0.440061 0.885206 0.031 Uiso calc 1 . .
H H13B 0.117236 -0.493315 0.762121 0.031 Uiso calc 1 . .
C C14 0.5686(4) 0.4771(4) 0.7139(3) 0.0231(6) Uani d 1 . .
H H14A 0.667670 0.429259 0.691921 0.028 Uiso calc 1 . .
H H14B 0.623427 0.549862 0.797431 0.028 Uiso calc 1 . .
C C15 0.5351(5) 0.5757(4) 0.6022(3) 0.0253(6) Uani d 1 . .
H H15A 0.447094 0.632955 0.628102 0.030 Uiso calc 1 . .
H H15B 0.665144 0.659131 0.586453 0.030 Uiso calc 1 . .
C C16 0.2536(5) 0.3306(4) 0.5001(3) 0.0240(6) Uani d 1 . .
H H16A 0.198514 0.256713 0.417103 0.029 Uiso calc 1 . .
H H16B 0.152583 0.375766 0.523119 0.029 Uiso calc 1 . .
C C17 0.2940(4) 0.2351(4) 0.6112(3) 0.0221(6) Uani d 1 . .
H H17A 0.167365 0.147006 0.626540 0.027 Uiso calc 1 . .
H H17B 0.388812 0.184215 0.586309 0.027 Uiso calc 1 . .
O O4 0.8307(4) 0.7243(3) 0.2157(2) 0.0292(5) Uani d 1 . .
H H4 0.845149 0.674900 0.282288 0.044 Uiso calc 1 . .
O O5 0.8281(4) 0.9108(3) 0.3721(2) 0.0338(5) Uani d 1 . .
O O6 0.9253(4) 1.4048(3) 0.1019(2) 0.0282(5) Uani d 1 . .
H H6 0.922943 1.426566 0.183393 0.042 Uiso calc 1 . .
O O7 0.7685(4) 0.9471(3) -0.2173(2) 0.0282(5) Uani d 1 . .
H H7 0.769716 1.019031 -0.268691 0.042 Uiso calc 1 . .
C C18 0.8310(5) 0.8689(4) 0.2561(3) 0.0245(6) Uani d 1 . .
C C19 0.8373(4) 0.9759(4) 0.1448(3) 0.0233(6) Uani d 1 . .
C C20 0.8753(4) 1.1395(4) 0.1782(3) 0.0230(6) Uani d 1 . .
H H20 0.894255 1.180995 0.269053 0.028 Uiso calc 1 . .
C C21 0.8855(4) 1.2429(4) 0.0771(3) 0.0230(6) Uani d 1 . .
C C22 0.8531(4) 1.1805(4) -0.0565(3) 0.0229(6) Uani d 1 . .
H H22 0.860643 1.250739 -0.125512 0.028 Uiso calc 1 . .
C C23 0.8099(4) 1.0150(4) -0.0877(3) 0.0231(6) Uani d 1 . .
C C24 0.8048(4) 0.9107(4) 0.0123(3) 0.0243(6) Uani d 1 . .
H H24 0.779908 0.798399 -0.009350 0.029 Uiso calc 1 . .
O O8 0.7775(4) 1.1327(3) -0.4306(2) 0.0309(5) Uani d 1 . .
H H8A 0.799(7) 1.230(7) -0.457(5) 0.046 Uiso d 1 . .
H H8B 0.779(7) 1.068(7) -0.492(5) 0.046 Uiso d 1 . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
C1 O2 H2 . . 109.5 ?
C9 N1 C11 . . 120.6(2) ?
C10 N1 C9 . . 119.9(3) ?
C10 N1 C11 . . 119.0(3) ?
C7 N2 C14 . . 115.7(2) ?
C7 N2 C17 . . 114.7(2) ?
C17 N2 C14 . . 111.0(2) ?
H3A N3 H3B . . 108.0 ?
C15 N3 H3A . . 109.3 ?
C15 N3 H3B . . 109.3 ?
C16 N3 H3A . . 109.3 ?
C16 N3 H3B . . 109.3 ?
C16 N3 C15 . . 111.4(2) ?
O1 C1 O2 . . 121.8(3) ?
O1 C1 C2 . . 121.2(3) ?
O2 C1 C2 . . 117.0(3) ?
C3 C2 C1 . . 121.3(3) ?
C10 C2 C1 . . 117.3(3) ?
C10 C2 C3 . . 121.4(3) ?
O3 C3 C2 . . 122.5(3) ?
O3 C3 C4 . . 122.3(3) ?
C2 C3 C4 . . 115.2(3) ?
C5 C4 C3 . . 120.8(3) ?
C5 C4 C9 . . 118.6(3) ?
C9 C4 C3 . . 120.6(3) ?
C4 C5 H5 . . 120.3 ?
C6 C5 C4 . . 119.5(3) ?
C6 C5 H5 . . 120.3 ?
F1 C6 C5 . . 119.0(3) ?
F1 C6 C7 . . 117.8(2) ?
C5 C6 C7 . . 123.2(3) ?
N2 C7 C6 . . 120.4(3) ?
C8 C7 N2 . . 122.6(3) ?
C8 C7 C6 . . 116.9(3) ?
C7 C8 H8 . . 119.4 ?
C7 C8 C9 . . 121.1(3) ?
C9 C8 H8 . . 119.4 ?
N1 C9 C4 . . 119.8(2) ?
C8 C9 N1 . . 119.6(3) ?
C8 C9 C4 . . 120.7(3) ?
N1 C10 C2 . . 123.0(3) ?
N1 C10 H10 . . 118.5 ?
C2 C10 H10 . . 118.5 ?
N1 C11 H11 . . 116.2 ?
N1 C11 C12 . . 118.9(3) ?
N1 C11 C13 . . 117.2(2) ?
C12 C11 H11 . . 116.2 ?
C13 C11 H11 . . 116.2 ?
C13 C11 C12 . . 60.8(2) ?
C11 C12 H12A . . 117.8 ?
C11 C12 H12B . . 117.8 ?
C11 C12 C13 . . 59.4(2) ?
H12A C12 H12B . . 115.0 ?
C13 C12 H12A . . 117.8 ?
C13 C12 H12B . . 117.8 ?
C11 C13 C12 . . 59.9(2) ?
C11 C13 H13A . . 117.8 ?
C11 C13 H13B . . 117.8 ?
C12 C13 H13A . . 117.8 ?
C12 C13 H13B . . 117.8 ?
H13A C13 H13B . . 114.9 ?
N2 C14 H14A . . 109.5 ?
N2 C14 H14B . . 109.5 ?
N2 C14 C15 . . 110.6(2) ?
H14A C14 H14B . . 108.1 ?
C15 C14 H14A . . 109.5 ?
C15 C14 H14B . . 109.5 ?
N3 C15 C14 . . 110.2(2) ?
N3 C15 H15A . . 109.6 ?
N3 C15 H15B . . 109.6 ?
C14 C15 H15A . . 109.6 ?
C14 C15 H15B . . 109.6 ?
H15A C15 H15B . . 108.1 ?
N3 C16 H16A . . 109.5 ?
N3 C16 H16B . . 109.5 ?
N3 C16 C17 . . 110.7(2) ?
H16A C16 H16B . . 108.1 ?
C17 C16 H16A . . 109.5 ?
C17 C16 H16B . . 109.5 ?
N2 C17 C16 . . 109.4(2) ?
N2 C17 H17A . . 109.8 ?
N2 C17 H17B . . 109.8 ?
C16 C17 H17A . . 109.8 ?
C16 C17 H17B . . 109.8 ?
H17A C17 H17B . . 108.2 ?
C18 O4 H4 . . 109.5 ?
C21 O6 H6 . . 109.5 ?
C23 O7 H7 . . 109.5 ?
O4 C18 C19 . . 113.1(3) ?
O5 C18 O4 . . 123.1(3) ?
O5 C18 C19 . . 123.8(3) ?
C20 C19 C18 . . 117.9(3) ?
C20 C19 C24 . . 121.7(3) ?
C24 C19 C18 . . 120.4(3) ?
C19 C20 H20 . . 120.3 ?
C19 C20 C21 . . 119.3(3) ?
C21 C20 H20 . . 120.3 ?
O6 C21 C20 . . 122.8(3) ?
O6 C21 C22 . . 117.1(3) ?
C20 C21 C22 . . 120.1(3) ?
C21 C22 H22 . . 120.2 ?
C23 C22 C21 . . 119.6(3) ?
C23 C22 H22 . . 120.2 ?
O7 C23 C22 . . 121.6(3) ?
O7 C23 C24 . . 117.3(3) ?
C22 C23 C24 . . 121.1(3) ?
C19 C24 C23 . . 118.2(3) ?
C19 C24 H24 . . 120.9 ?
C23 C24 H24 . . 120.9 ?
H8A O8 H8B . . 112(5) ?
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 C6 . 1.357(4) ?
O1 C1 . 1.227(4) ?
O2 H2 . 0.8400 ?
O2 C1 . 1.314(4) ?
O3 C3 . 1.263(4) ?
N1 C9 . 1.397(4) ?
N1 C10 . 1.339(4) ?
N1 C11 . 1.463(4) ?
N2 C7 . 1.407(4) ?
N2 C14 . 1.468(4) ?
N2 C17 . 1.467(4) ?
N3 H3A . 0.9100 ?
N3 H3B . 0.9100 ?
N3 C15 . 1.489(4) ?
N3 C16 . 1.484(4) ?
C1 C2 . 1.475(4) ?
C2 C3 . 1.428(4) ?
C2 C10 . 1.369(4) ?
C3 C4 . 1.457(4) ?
C4 C5 . 1.406(4) ?
C4 C9 . 1.407(4) ?
C5 H5 . 0.9500 ?
C5 C6 . 1.358(4) ?
C6 C7 . 1.419(4) ?
C7 C8 . 1.384(4) ?
C8 H8 . 0.9500 ?
C8 C9 . 1.394(4) ?
C10 H10 . 0.9500 ?
C11 H11 . 1.0000 ?
C11 C12 . 1.499(4) ?
C11 C13 . 1.492(4) ?
C12 H12A . 0.9900 ?
C12 H12B . 0.9900 ?
C12 C13 . 1.513(4) ?
C13 H13A . 0.9900 ?
C13 H13B . 0.9900 ?
C14 H14A . 0.9900 ?
C14 H14B . 0.9900 ?
C14 C15 . 1.517(4) ?
C15 H15A . 0.9900 ?
C15 H15B . 0.9900 ?
C16 H16A . 0.9900 ?
C16 H16B . 0.9900 ?
C16 C17 . 1.510(4) ?
C17 H17A . 0.9900 ?
C17 H17B . 0.9900 ?
O4 H4 . 0.8400 ?
O4 C18 . 1.320(4) ?
O5 C18 . 1.216(4) ?
O6 H6 . 0.8400 ?
O6 C21 . 1.356(4) ?
O7 H7 . 0.8400 ?
O7 C23 . 1.372(4) ?
C18 C19 . 1.501(4) ?
C19 C20 . 1.385(4) ?
C19 C24 . 1.395(4) ?
C20 H20 . 0.9500 ?
C20 C21 . 1.395(4) ?
C21 C22 . 1.399(4) ?
C22 H22 . 0.9500 ?
C22 C23 . 1.389(5) ?
C23 C24 . 1.398(4) ?
C24 H24 . 0.9500 ?
O8 H8A . 0.88(6) ?
O8 H8B . 0.82(6) ?
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
O2 H2 O3 . 0.84 1.78 2.551(3) 152 yes
N3 H3A O1 1_564 0.91 1.75 2.652(3) 172 yes
N3 H3B Cl1 . 0.91 2.30 3.106(3) 148 yes
C10 H10 F1 1_545 0.95 2.46 3.158(4) 130 yes
C12 H12B O7 1_446 0.99 2.47 3.435(4) 166 yes
C14 H14B F1 . 0.99 2.27 2.927(3) 123 yes
C16 H16B Cl1 1_455 0.99 2.78 3.609(3) 142 yes
O4 H4 Cl1 . 0.84 2.28 3.082(2) 160 yes
O6 H6 Cl1 1_565 0.84 2.40 3.232(2) 170 yes
O7 H7 O8 . 0.84 1.96 2.769(3) 161 yes
O8 H8A Cl1 1_564 0.88(6) 2.51(6) 3.362(3) 164(4) yes
O8 H8B O5 1_554 0.82(6) 2.05(6) 2.865(4) 170(5) 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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
F1 C6 C7 N2 . . . . -2.4(4) ?
F1 C6 C7 C8 . . . . -178.8(3) ?
O1 C1 C2 C3 . . . . -173.3(3) ?
O1 C1 C2 C10 . . . . 4.3(4) ?
O2 C1 C2 C3 . . . . 5.9(4) ?
O2 C1 C2 C10 . . . . -176.5(3) ?
O3 C3 C4 C5 . . . . 2.6(4) ?
O3 C3 C4 C9 . . . . -179.1(3) ?
N1 C11 C12 C13 . . . . -106.9(3) ?
N1 C11 C13 C12 . . . . 109.5(3) ?
N2 C7 C8 C9 . . . . -175.5(3) ?
N2 C14 C15 N3 . . . . -55.7(3) ?
N3 C16 C17 N2 . . . . 58.0(3) ?
C1 C2 C3 O3 . . . . -4.2(4) ?
C1 C2 C3 C4 . . . . 174.7(3) ?
C1 C2 C10 N1 . . . . -177.1(3) ?
C2 C3 C4 C5 . . . . -176.4(3) ?
C2 C3 C4 C9 . . . . 2.0(4) ?
C3 C2 C10 N1 . . . . 0.5(4) ?
C3 C4 C5 C6 . . . . 179.1(3) ?
C3 C4 C9 N1 . . . . 1.1(4) ?
C3 C4 C9 C8 . . . . -178.0(3) ?
C4 C5 C6 F1 . . . . 178.0(3) ?
C4 C5 C6 C7 . . . . -1.1(5) ?
C5 C4 C9 N1 . . . . 179.5(3) ?
C5 C4 C9 C8 . . . . 0.4(4) ?
C5 C6 C7 N2 . . . . 176.7(3) ?
C5 C6 C7 C8 . . . . 0.3(4) ?
C6 C7 C8 C9 . . . . 0.8(4) ?
C7 N2 C14 C15 . . . . -167.8(2) ?
C7 N2 C17 C16 . . . . 166.7(2) ?
C7 C8 C9 N1 . . . . 179.7(3) ?
C7 C8 C9 C4 . . . . -1.2(4) ?
C9 N1 C10 C2 . . . . 2.9(4) ?
C9 N1 C11 C12 . . . . -70.4(4) ?
C9 N1 C11 C13 . . . . -140.3(3) ?
C9 C4 C5 C6 . . . . 0.7(4) ?
C10 N1 C9 C4 . . . . -3.6(4) ?
C10 N1 C9 C8 . . . . 175.5(3) ?
C10 N1 C11 C12 . . . . 117.4(3) ?
C10 N1 C11 C13 . . . . 47.5(4) ?
C10 C2 C3 O3 . . . . 178.2(3) ?
C10 C2 C3 C4 . . . . -2.9(4) ?
C11 N1 C9 C4 . . . . -175.7(2) ?
C11 N1 C9 C8 . . . . 3.4(4) ?
C11 N1 C10 C2 . . . . 175.1(3) ?
C14 N2 C7 C6 . . . . 62.4(4) ?
C14 N2 C7 C8 . . . . -121.4(3) ?
C14 N2 C17 C16 . . . . -59.9(3) ?
C15 N3 C16 C17 . . . . -56.1(3) ?
C16 N3 C15 C14 . . . . 54.5(3) ?
C17 N2 C7 C6 . . . . -166.4(3) ?
C17 N2 C7 C8 . . . . 9.8(4) ?
C17 N2 C14 C15 . . . . 59.2(3) ?
O4 C18 C19 C20 . . . . -168.3(3) ?
O4 C18 C19 C24 . . . . 11.9(4) ?
O5 C18 C19 C20 . . . . 11.1(5) ?
O5 C18 C19 C24 . . . . -168.6(3) ?
O6 C21 C22 C23 . . . . -179.4(3) ?
O7 C23 C24 C19 . . . . -177.1(3) ?
C18 C19 C20 C21 . . . . 178.9(3) ?
C18 C19 C24 C23 . . . . 179.2(3) ?
C19 C20 C21 O6 . . . . -178.9(3) ?
C19 C20 C21 C22 . . . . 1.4(4) ?
C20 C19 C24 C23 . . . . -0.5(4) ?
C20 C21 C22 C23 . . . . 0.3(4) ?
C21 C22 C23 O7 . . . . 177.1(3) ?
C21 C22 C23 C24 . . . . -2.2(4) ?
C22 C23 C24 C19 . . . . 2.3(4) ?
C24 C19 C20 C21 . . . . -1.3(4) ?

_cod_database_fobs_code 2244034
