#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/79/2017996.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_2017996
loop_
_publ_author_name
'Fabbiani, Francesca P. A.'
'Arlin, Jean-Baptiste'
'Buth, Gernot'
'Dittrich, Birger'
'Florence, Alastair J.'
'Herbst-Irmer, Regine'
'Sowa, Heidrun'
_publ_section_title
;
 Intermolecular interactions, disorder and twinning in
 ciprofloxacin--2,2-difluoroethanol (2/3) and ciprofloxacin--water
 (3/14.5)
;
_journal_coeditor_code           BI3008
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o120
_journal_page_last               o124
_journal_paper_doi               10.1107/S0108270111005488
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          '2C17 H18 F N3 O3 , 3C2 H4 F2 O'
_chemical_formula_moiety         '2(C17 H18 F N3 O3), 3(C2 H4 F2 O)'
_chemical_formula_sum            'C40 H48 F8 N6 O9'
_chemical_formula_weight         908.84
_chemical_name_common
;
ciprofloxacin--2,2-difluoroethanol (2/3)
;
_chemical_name_systematic
;
1-cyclopropyl-6-fluoro-4-oxo-7-(piperazin-4-ium-1-yl)-1,4-dihydroquinoline-3-
carboxylate--2,2-difluoroethanol (2/3)
;
_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
_audit_creation_method           SHELXL97
_cell_angle_alpha                105.6488(18)
_cell_angle_beta                 90.352(2)
_cell_angle_gamma                93.364(2)
_cell_formula_units_Z            2
_cell_length_a                   10.9848(4)
_cell_length_b                   13.9800(4)
_cell_length_c                   13.9802(4)
_cell_measurement_reflns_used    9991
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      24.6
_cell_measurement_theta_min      2.3
_cell_volume                     2063.22(11)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics
;
ORTEP3 for Windows (Burnett & Johnson, 1996)
and Mercury (Macrae et al., 2008)
;
_computing_publication_material  'publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008b)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008b)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.969
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_device_type  'Bruker SMART APEXII CCD area-detector'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  silicon
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.7000
_diffrn_reflns_av_R_equivalents  0.08
_diffrn_reflns_av_sigmaI/netI    0.0490
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            51821
_diffrn_reflns_theta_full        24.64
_diffrn_reflns_theta_max         24.64
_diffrn_reflns_theta_min         1.49
_exptl_absorpt_coefficient_mu    0.127
_exptl_absorpt_correction_T_max  0.74
_exptl_absorpt_correction_T_min  0.58
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(TWINABS; Sheldrick, 2008a)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.463
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             948
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.578
_refine_diff_density_min         -0.461
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.164
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     571
_refine_ls_number_reflns         7072
_refine_ls_number_restraints     522
_refine_ls_restrained_S_all      1.122
_refine_ls_R_factor_all          0.0812
_refine_ls_R_factor_gt           0.0681
_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)+(0.0922P)²+1.8862P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1907
_refine_ls_wR_factor_ref         0.2019
_reflns_number_gt                5962
_reflns_number_total             7072
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bi3008.cif
_cod_data_source_block           I
_cod_database_code               2017996
_cod_database_fobs_code          2017996
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_disorder_assembly
_atom_site_disorder_group
C C1A 0.9157(4) 0.6677(3) 0.9873(3) 0.0288(8) Uani d DU 1 . .
H H1A 0.9913 0.6568 0.9501 0.035 Uiso calc R 1 . .
C C2A 0.8581(5) 0.5807(3) 1.0157(3) 0.0420(11) Uani d DU 1 . .
H H2A1 0.8170 0.5932 1.0787 0.050 Uiso calc R 1 . .
H H2A2 0.8986 0.5188 0.9970 0.050 Uiso calc R 1 . .
C C3A 0.8011(4) 0.6155(3) 0.9344(3) 0.0386(10) Uani d DU 1 . .
H H3A1 0.7260 0.6493 0.9483 0.046 Uiso calc R 1 . .
H H3A2 0.8077 0.5748 0.8666 0.046 Uiso calc R 1 . .
C C4A 0.8842(3) 0.8470(3) 1.0175(3) 0.0235(8) Uani d DU 1 . .
C C5A 0.9123(3) 0.7794(3) 1.1540(3) 0.0266(8) Uani d DU 1 . .
H H5A 0.9317 0.7250 1.1762 0.032 Uiso calc R 1 . .
C C6A 0.8930(3) 0.8662(3) 1.2250(3) 0.0249(8) Uani d DU 1 . .
C C7A 0.9057(3) 0.8645(3) 1.3323(3) 0.0255(8) Uani d DU 1 . .
C C8A 0.8585(3) 0.9511(3) 1.1929(2) 0.0219(7) Uani d DU 1 . .
C C9A 0.8628(3) 0.9378(3) 1.0849(3) 0.0241(8) Uani d DU 1 . .
C C10A 0.8422(3) 1.0192(3) 1.0475(3) 0.0237(8) Uani d DU 1 . .
H H10A 0.8266 1.0805 1.0905 0.028 Uiso calc R 1 . .
C C11A 0.8452(3) 1.0080(3) 0.9483(3) 0.0248(8) Uani d DU 1 . .
C C12A 0.8640(3) 0.9176(3) 0.8782(2) 0.0222(7) Uani d DU 1 . .
C C13A 0.9126(3) 0.8245(3) 0.7086(2) 0.0243(8) Uani d DU 1 . .
H H13A 0.8502 0.7704 0.6971 0.029 Uiso calc R 1 . .
H H13B 0.9841 0.8044 0.7373 0.029 Uiso calc R 1 . .
C C14A 0.9448(3) 0.8467(3) 0.6104(3) 0.0240(8) Uani d DU 1 . .
H H14A 1.0137 0.8953 0.6212 0.029 Uiso calc R 1 . .
H H14B 0.9687 0.7863 0.5635 0.029 Uiso calc R 1 . .
C C15A 0.7919(3) 0.9719(3) 0.6399(2) 0.0245(8) Uani d DU 1 . .
H H15A 0.7201 0.9920 0.6115 0.029 Uiso calc R 1 . .
H H15B 0.8525 1.0275 0.6546 0.029 Uiso calc R 1 . .
C C16A 0.7589(3) 0.9448(3) 0.7348(3) 0.0246(8) Uani d DU 1 . .
H H16A 0.7278 1.0018 0.7822 0.030 Uiso calc R 1 . .
H H16B 0.6958 0.8912 0.7207 0.030 Uiso calc R 1 . .
C C17A 0.8836(3) 0.8363(3) 0.9151(3) 0.0243(8) Uani d DU 1 . .
H H17A 0.8962 0.7747 0.8715 0.029 Uiso calc R 1 . .
F F1A 0.8334(2) 1.09146(15) 0.91582(15) 0.0284(5) Uani d DU 1 . .
N N1A 0.9055(3) 0.7661(2) 1.0551(2) 0.0251(7) Uani d DU 1 . .
N N2A 0.8682(3) 0.9135(2) 0.7771(2) 0.0239(7) Uani d DU 1 . .
N N3A 0.8410(3) 0.8854(2) 0.5674(2) 0.0228(6) Uani d DU 1 . .
H H3A4 0.7814 0.8368 0.5481 0.027 Uiso calc R 1 . .
H H3A3 0.8656 0.9037 0.5133 0.027 Uiso calc R 1 . .
O O1A 0.9278(3) 0.7830(2) 1.3494(2) 0.0404(8) Uani d DU 1 . .
O O2A 0.8963(2) 0.94404(19) 1.39869(17) 0.0276(6) Uani d DU 1 . .
O O3A 0.8274(2) 1.03187(18) 1.24727(17) 0.0253(6) Uani d DU 1 . .
C C1B 0.4484(4) 0.5514(3) 0.8104(3) 0.0319(9) Uani d DU 1 . .
H H1B 0.5207 0.5962 0.8113 0.038 Uiso calc R 1 . .
C C2B 0.4191(4) 0.5314(3) 0.9062(3) 0.0395(10) Uani d DU 1 . .
H H2B1 0.4733 0.5618 0.9627 0.047 Uiso calc R 1 . .
H H2B2 0.3838 0.4657 0.9049 0.047 Uiso calc R 1 . .
C C3B 0.3424(4) 0.5984(3) 0.8669(3) 0.0384(10) Uani d DU 1 . .
H H3B1 0.2610 0.5731 0.8415 0.046 Uiso calc R 1 . .
H H3B2 0.3506 0.6692 0.8993 0.046 Uiso calc R 1 . .
C C4B 0.3889(3) 0.5089(3) 0.6346(3) 0.0254(8) Uani d DU 1 . .
C C5B 0.4229(3) 0.3788(3) 0.7091(3) 0.0260(8) Uani d DU 1 . .
H H5B 0.4454 0.3602 0.7655 0.031 Uiso calc R 1 . .
C C6B 0.3937(3) 0.3040(3) 0.6251(3) 0.0256(8) Uani d DU 1 . .
C C7B 0.4001(3) 0.1985(3) 0.6308(3) 0.0245(8) Uani d DU 1 . .
C C8B 0.3571(3) 0.3298(3) 0.5358(3) 0.0242(8) Uani d DU 1 . .
C C9B 0.3582(3) 0.4370(3) 0.5460(3) 0.0254(8) Uani d DU 1 . .
C C10B 0.3259(3) 0.4710(3) 0.4636(3) 0.0250(8) Uani d DU 1 . .
H H10B 0.3040 0.4254 0.4033 0.030 Uiso calc R 1 . .
C C11B 0.3266(3) 0.5694(3) 0.4719(3) 0.0267(8) Uani d DU 1 . .
C C12B 0.3567(3) 0.6433(3) 0.5603(3) 0.0240(7) Uani d DU 1 . .
C C13B 0.4146(4) 0.8152(3) 0.6520(3) 0.0282(8) Uani d DU 1 . .
H H13C 0.4908 0.7916 0.6693 0.034 Uiso calc R 1 . .
H H13D 0.3601 0.8207 0.7073 0.034 Uiso calc R 1 . .
C C14B 0.4377(3) 0.9162(3) 0.6323(3) 0.0268(8) Uani d DU 1 . .
H H14C 0.4701 0.9638 0.6923 0.032 Uiso calc R 1 . .
H H14D 0.4981 0.9115 0.5811 0.032 Uiso calc R 1 . .
C C15B 0.2663(4) 0.8780(3) 0.5124(3) 0.0273(8) Uani d DU 1 . .
H H15C 0.3193 0.8700 0.4559 0.033 Uiso calc R 1 . .
H H15D 0.1897 0.9011 0.4952 0.033 Uiso calc R 1 . .
C C16B 0.2436(3) 0.7792(3) 0.5365(3) 0.0260(8) Uani d DU 1 . .
H H16C 0.1885 0.7868 0.5917 0.031 Uiso calc R 1 . .
H H16D 0.2057 0.7305 0.4795 0.031 Uiso calc R 1 . .
C C17B 0.3875(3) 0.6100(3) 0.6421(3) 0.0260(8) Uani d DU 1 . .
H H17B 0.4075 0.6561 0.7026 0.031 Uiso calc R 1 . .
F F1B 0.3010(2) 0.59818(16) 0.38806(15) 0.0318(5) Uani d DU 1 . .
N N1B 0.4220(3) 0.4767(2) 0.7173(2) 0.0278(7) Uani d DU 1 . .
N N2B 0.3597(3) 0.7443(2) 0.5626(2) 0.0261(7) Uani d DU 1 . .
N N3B 0.3242(3) 0.9521(2) 0.5999(2) 0.0247(7) Uani d DU 1 . .
H H3B3 0.3418 1.0098 0.5844 0.030 Uiso calc R 1 . .
H H3B4 0.2716 0.9640 0.6503 0.030 Uiso calc R 1 . .
O O1B 0.4321(3) 0.18655(19) 0.71462(19) 0.0313(6) Uani d DU 1 . .
O O2B 0.3747(2) 0.12815(18) 0.55542(18) 0.0277(6) Uani d DU 1 . .
O O3B 0.3268(2) 0.27002(19) 0.45403(18) 0.0280(6) Uani d DU 1 . .
O O4A 0.1169(3) 0.4141(2) 0.7139(2) 0.0451(8) Uani d . 1 . .
H H4A 0.1199 0.3536 0.6935 0.068 Uiso calc R 1 . .
C C18A 0.0222(5) 0.4457(4) 0.6626(4) 0.0489(12) Uani d . 1 . .
H H18A -0.0543 0.4424 0.6961 0.059 Uiso calc R 1 . .
H H18B 0.0129 0.4027 0.5954 0.059 Uiso calc R 1 . .
C C19A 0.0542(4) 0.5481(3) 0.6604(4) 0.0414(11) Uani d . 1 . .
H H19A 0.1343 0.5522 0.6306 0.050 Uiso calc R 1 . .
F F2A -0.0329(3) 0.5799(2) 0.6068(2) 0.0654(9) Uani d . 1 . .
F F3A 0.0543(4) 0.6118(2) 0.7516(3) 0.0825(12) Uani d . 1 . .
O O4B 0.3352(3) 0.8446(2) 0.2558(2) 0.0403(7) Uani d . 1 . .
H H4B 0.4026 0.8337 0.2747 0.061 Uiso calc R 1 . .
C C18B 0.2516(4) 0.7633(3) 0.2550(3) 0.0383(10) Uani d . 1 . .
H H18C 0.1735 0.7881 0.2785 0.046 Uiso calc R 1 . .
H H18D 0.2812 0.7273 0.3000 0.046 Uiso calc R 1 . .
C C19B 0.2353(4) 0.6951(3) 0.1550(3) 0.0430(11) Uani d . 1 . .
H H19B 0.2178 0.7332 0.1076 0.052 Uiso calc R 1 . .
F F2B 0.3369(3) 0.6442(2) 0.1268(2) 0.0624(8) Uani d . 1 . .
F F3B 0.1414(3) 0.6267(2) 0.1530(2) 0.0614(8) Uani d . 1 . .
O O4C 0.6097(3) 0.7792(3) 1.0868(2) 0.0481(8) Uani d . 1 . .
H H4C 0.6047 0.7833 1.1462 0.072 Uiso calc R 1 . .
C C18C 0.5157(4) 0.8319(4) 1.0576(3) 0.0440(11) Uani d . 1 . .
H H18E 0.5037 0.8923 1.1094 0.053 Uiso calc R 1 . .
H H18F 0.4397 0.7911 1.0465 0.053 Uiso calc R 1 . .
C C19C 0.5525(4) 0.8567(3) 0.9642(3) 0.0363(10) Uani d . 1 . .
H H19C 0.6269 0.9009 0.9756 0.044 Uiso calc R 1 . .
F F2C 0.5685(3) 0.7732(2) 0.89043(19) 0.0515(7) Uani d . 1 . .
F F3C 0.4582(3) 0.9011(2) 0.9317(2) 0.0612(8) Uani 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 0.0033 0.0016 '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'
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'
H H 0.0000 0.0000 '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
N1A C1A C2A . . 118.0(3) ?
N1A C1A C3A . . 117.2(3) ?
C2A C1A C3A . . 60.2(3) ?
N1A C1A H1A . . 116.5 ?
C2A C1A H1A . . 116.5 ?
C3A C1A H1A . . 116.5 ?
C1A C2A C3A . . 60.4(3) ?
C1A C2A H2A1 . . 117.7 ?
C3A C2A H2A1 . . 117.7 ?
C1A C2A H2A2 . . 117.7 ?
C3A C2A H2A2 . . 117.7 ?
H2A1 C2A H2A2 . . 114.9 ?
C2A C3A C1A . . 59.4(3) ?
C2A C3A H3A1 . . 117.8 ?
C1A C3A H3A1 . . 117.8 ?
C2A C3A H3A2 . . 117.8 ?
C1A C3A H3A2 . . 117.8 ?
H3A1 C3A H3A2 . . 115.0 ?
C9A C4A C17A . . 121.3(3) ?
C9A C4A N1A . . 118.1(3) ?
C17A C4A N1A . . 120.6(3) ?
N1A C5A C6A . . 125.7(3) ?
N1A C5A H5A . . 117.2 ?
C6A C5A H5A . . 117.2 ?
C5A C6A C8A . . 118.5(3) ?
C5A C6A C7A . . 116.8(3) ?
C8A C6A C7A . . 124.6(3) ?
O2A C7A O1A . . 123.9(3) ?
O2A C7A C6A . . 118.4(3) ?
O1A C7A C6A . . 117.7(3) ?
O3A C8A C6A . . 126.5(3) ?
O3A C8A C9A . . 118.9(3) ?
C6A C8A C9A . . 114.6(3) ?
C4A C9A C10A . . 118.3(3) ?
C4A C9A C8A . . 122.9(3) ?
C10A C9A C8A . . 118.8(3) ?
C11A C10A C9A . . 119.5(3) ?
C11A C10A H10A . . 120.2 ?
C9A C10A H10A . . 120.2 ?
C10A C11A F1A . . 117.4(3) ?
C10A C11A C12A . . 123.8(3) ?
F1A C11A C12A . . 118.8(3) ?
C17A C12A N2A . . 123.4(3) ?
C17A C12A C11A . . 116.7(3) ?
N2A C12A C11A . . 119.8(3) ?
N2A C13A C14A . . 109.5(3) ?
N2A C13A H13A . . 109.8 ?
C14A C13A H13A . . 109.8 ?
N2A C13A H13B . . 109.8 ?
C14A C13A H13B . . 109.8 ?
H13A C13A H13B . . 108.2 ?
N3A C14A C13A . . 111.9(3) ?
N3A C14A H14A . . 109.2 ?
C13A C14A H14A . . 109.2 ?
N3A C14A H14B . . 109.2 ?
C13A C14A H14B . . 109.2 ?
H14A C14A H14B . . 107.9 ?
N3A C15A C16A . . 110.1(3) ?
N3A C15A H15A . . 109.6 ?
C16A C15A H15A . . 109.6 ?
N3A C15A H15B . . 109.6 ?
C16A C15A H15B . . 109.6 ?
H15A C15A H15B . . 108.2 ?
N2A C16A C15A . . 109.4(3) ?
N2A C16A H16A . . 109.8 ?
C15A C16A H16A . . 109.8 ?
N2A C16A H16B . . 109.8 ?
C15A C16A H16B . . 109.8 ?
H16A C16A H16B . . 108.2 ?
C12A C17A C4A . . 120.3(3) ?
C12A C17A H17A . . 119.9 ?
C4A C17A H17A . . 119.9 ?
C5A N1A C4A . . 119.6(3) ?
C5A N1A C1A . . 120.4(3) ?
C4A N1A C1A . . 120.0(3) ?
C12A N2A C13A . . 118.2(3) ?
C12A N2A C16A . . 115.8(3) ?
C13A N2A C16A . . 110.5(3) ?
C14A N3A C15A . . 111.6(3) ?
C14A N3A H3A4 . . 109.3 ?
C15A N3A H3A4 . . 109.3 ?
C14A N3A H3A3 . . 109.3 ?
C15A N3A H3A3 . . 109.3 ?
H3A4 N3A H3A3 . . 108.0 ?
N1B C1B C2B . . 121.1(3) ?
N1B C1B C3B . . 117.2(4) ?
C2B C1B C3B . . 60.8(3) ?
N1B C1B H1B . . 115.5 ?
C2B C1B H1B . . 115.5 ?
C3B C1B H1B . . 115.5 ?
C1B C2B C3B . . 60.3(3) ?
C1B C2B H2B1 . . 117.7 ?
C3B C2B H2B1 . . 117.7 ?
C1B C2B H2B2 . . 117.7 ?
C3B C2B H2B2 . . 117.7 ?
H2B1 C2B H2B2 . . 114.9 ?
C1B C3B C2B . . 58.9(3) ?
C1B C3B H3B1 . . 117.9 ?
C2B C3B H3B1 . . 117.9 ?
C1B C3B H3B2 . . 117.9 ?
C2B C3B H3B2 . . 117.9 ?
H3B1 C3B H3B2 . . 115.0 ?
C17B C4B C9B . . 121.7(3) ?
C17B C4B N1B . . 120.2(3) ?
C9B C4B N1B . . 118.1(3) ?
N1B C5B C6B . . 125.7(3) ?
N1B C5B H5B . . 117.2 ?
C6B C5B H5B . . 117.2 ?
C5B C6B C8B . . 118.9(3) ?
C5B C6B C7B . . 117.8(3) ?
C8B C6B C7B . . 123.3(3) ?
O2B C7B O1B . . 123.6(3) ?
O2B C7B C6B . . 119.7(3) ?
O1B C7B C6B . . 116.7(3) ?
O3B C8B C6B . . 126.3(3) ?
O3B C8B C9B . . 119.2(3) ?
C6B C8B C9B . . 114.5(3) ?
C4B C9B C10B . . 117.2(3) ?
C4B C9B C8B . . 123.2(3) ?
C10B C9B C8B . . 119.6(3) ?
C11B C10B C9B . . 120.3(3) ?
C11B C10B H10B . . 119.9 ?
C9B C10B H10B . . 119.9 ?
C10B C11B F1B . . 117.7(3) ?
C10B C11B C12B . . 123.6(3) ?
F1B C11B C12B . . 118.6(3) ?
C17B C12B N2B . . 123.1(3) ?
C17B C12B C11B . . 116.3(3) ?
N2B C12B C11B . . 120.5(3) ?
N2B C13B C14B . . 109.4(3) ?
N2B C13B H13C . . 109.8 ?
C14B C13B H13C . . 109.8 ?
N2B C13B H13D . . 109.8 ?
C14B C13B H13D . . 109.8 ?
H13C C13B H13D . . 108.3 ?
N3B C14B C13B . . 111.4(3) ?
N3B C14B H14C . . 109.3 ?
C13B C14B H14C . . 109.3 ?
N3B C14B H14D . . 109.3 ?
C13B C14B H14D . . 109.3 ?
H14C C14B H14D . . 108.0 ?
N3B C15B C16B . . 109.5(3) ?
N3B C15B H15C . . 109.8 ?
C16B C15B H15C . . 109.8 ?
N3B C15B H15D . . 109.8 ?
C16B C15B H15D . . 109.8 ?
H15C C15B H15D . . 108.2 ?
N2B C16B C15B . . 109.8(3) ?
N2B C16B H16C . . 109.7 ?
C15B C16B H16C . . 109.7 ?
N2B C16B H16D . . 109.7 ?
C15B C16B H16D . . 109.7 ?
H16C C16B H16D . . 108.2 ?
C4B C17B C12B . . 120.9(3) ?
C4B C17B H17B . . 119.6 ?
C12B C17B H17B . . 119.6 ?
C5B N1B C4B . . 119.6(3) ?
C5B N1B C1B . . 122.3(3) ?
C4B N1B C1B . . 118.0(3) ?
C12B N2B C13B . . 116.6(3) ?
C12B N2B C16B . . 115.1(3) ?
C13B N2B C16B . . 110.1(3) ?
C14B N3B C15B . . 111.2(3) ?
C14B N3B H3B3 . . 109.4 ?
C15B N3B H3B3 . . 109.4 ?
C14B N3B H3B4 . . 109.4 ?
C15B N3B H3B4 . . 109.4 ?
H3B3 N3B H3B4 . . 108.0 ?
C18A O4A H4A . . 109.5 ?
O4A C18A C19A . . 108.3(4) ?
O4A C18A H18A . . 110.0 ?
C19A C18A H18A . . 110.0 ?
O4A C18A H18B . . 110.0 ?
C19A C18A H18B . . 110.0 ?
H18A C18A H18B . . 108.4 ?
F3A C19A F2A . . 104.9(4) ?
F3A C19A C18A . . 111.7(4) ?
F2A C19A C18A . . 110.0(4) ?
F3A C19A H19A . . 110.0 ?
F2A C19A H19A . . 110.0 ?
C18A C19A H19A . . 110.0 ?
C18B O4B H4B . . 109.5 ?
O4B C18B C19B . . 111.5(4) ?
O4B C18B H18C . . 109.3 ?
C19B C18B H18C . . 109.3 ?
O4B C18B H18D . . 109.3 ?
C19B C18B H18D . . 109.3 ?
H18C C18B H18D . . 108.0 ?
F3B C19B F2B . . 107.3(4) ?
F3B C19B C18B . . 110.3(4) ?
F2B C19B C18B . . 111.2(4) ?
F3B C19B H19B . . 109.4 ?
F2B C19B H19B . . 109.4 ?
C18B C19B H19B . . 109.4 ?
C18C O4C H4C . . 109.5 ?
O4C C18C C19C . . 108.2(4) ?
O4C C18C H18E . . 110.1 ?
C19C C18C H18E . . 110.1 ?
O4C C18C H18F . . 110.1 ?
C19C C18C H18F . . 110.1 ?
H18E C18C H18F . . 108.4 ?
F2C C19C F3C . . 105.3(3) ?
F2C C19C C18C . . 111.1(4) ?
F3C C19C C18C . . 108.5(4) ?
F2C C19C H19C . . 110.6 ?
F3C C19C H19C . . 110.6 ?
C18C C19C H19C . . 110.6 ?
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
C1A N1A . 1.456(5) ?
C1A C2A . 1.487(5) ?
C1A C3A . 1.502(6) ?
C1A H1A . 0.980 ?
C2A C3A . 1.498(6) ?
C2A H2A1 . 0.970 ?
C2A H2A2 . 0.970 ?
C3A H3A1 . 0.970 ?
C3A H3A2 . 0.970 ?
C4A C9A . 1.395(5) ?
C4A C17A . 1.397(5) ?
C4A N1A . 1.400(4) ?
C5A N1A . 1.346(4) ?
C5A C6A . 1.373(5) ?
C5A H5A . 0.930 ?
C6A C8A . 1.446(5) ?
C6A C7A . 1.512(5) ?
C7A O2A . 1.251(4) ?
C7A O1A . 1.263(4) ?
C8A O3A . 1.246(4) ?
C8A C9A . 1.473(5) ?
C9A C10A . 1.404(5) ?
C10A C11A . 1.353(5) ?
C10A H10A . 0.930 ?
C11A F1A . 1.374(4) ?
C11A C12A . 1.402(5) ?
C12A C17A . 1.396(5) ?
C12A N2A . 1.400(4) ?
C13A N2A . 1.462(4) ?
C13A C14A . 1.526(5) ?
C13A H13A . 0.970 ?
C13A H13B . 0.970 ?
C14A N3A . 1.481(4) ?
C14A H14A . 0.970 ?
C14A H14B . 0.970 ?
C15A N3A . 1.484(4) ?
C15A C16A . 1.515(5) ?
C15A H15A . 0.970 ?
C15A H15B . 0.970 ?
C16A N2A . 1.475(4) ?
C16A H16A . 0.970 ?
C16A H16B . 0.970 ?
C17A H17A . 0.930 ?
N3A H3A4 . 0.900 ?
N3A H3A3 . 0.900 ?
C1B N1B . 1.449(5) ?
C1B C2B . 1.474(5) ?
C1B C3B . 1.494(6) ?
C1B H1B . 0.980 ?
C2B C3B . 1.502(6) ?
C2B H2B1 . 0.970 ?
C2B H2B2 . 0.970 ?
C3B H3B1 . 0.970 ?
C3B H3B2 . 0.970 ?
C4B C17B . 1.390(5) ?
C4B C9B . 1.393(5) ?
C4B N1B . 1.402(4) ?
C5B N1B . 1.343(5) ?
C5B C6B . 1.366(5) ?
C5B H5B . 0.930 ?
C6B C8B . 1.450(5) ?
C6B C7B . 1.505(5) ?
C7B O2B . 1.249(4) ?
C7B O1B . 1.278(4) ?
C8B O3B . 1.250(4) ?
C8B C9B . 1.466(5) ?
C9B C10B . 1.411(5) ?
C10B C11B . 1.348(5) ?
C10B H10B . 0.930 ?
C11B F1B . 1.370(4) ?
C11B C12B . 1.404(5) ?
C12B C17B . 1.392(5) ?
C12B N2B . 1.402(4) ?
C13B N2B . 1.470(5) ?
C13B C14B . 1.518(5) ?
C13B H13C . 0.970 ?
C13B H13D . 0.970 ?
C14B N3B . 1.483(5) ?
C14B H14C . 0.970 ?
C14B H14D . 0.970 ?
C15B N3B . 1.485(5) ?
C15B C16B . 1.515(5) ?
C15B H15C . 0.970 ?
C15B H15D . 0.970 ?
C16B N2B . 1.470(4) ?
C16B H16C . 0.970 ?
C16B H16D . 0.970 ?
C17B H17B . 0.930 ?
N3B H3B3 . 0.900 ?
N3B H3B4 . 0.900 ?
O4A C18A . 1.417(5) ?
O4A H4A . 0.820 ?
C18A C19A . 1.463(6) ?
C18A H18A . 0.970 ?
C18A H18B . 0.970 ?
C19A F3A . 1.344(6) ?
C19A F2A . 1.376(5) ?
C19A H19A . 0.980 ?
O4B C18B . 1.416(5) ?
O4B H4B . 0.820 ?
C18B C19B . 1.467(6) ?
C18B H18C . 0.970 ?
C18B H18D . 0.970 ?
C19B F3B . 1.360(6) ?
C19B F2B . 1.362(5) ?
C19B H19B . 0.980 ?
O4C C18C . 1.422(6) ?
O4C H4C . 0.820 ?
C18C C19C . 1.491(6) ?
C18C H18E . 0.970 ?
C18C H18F . 0.970 ?
C19C F2C . 1.354(5) ?
C19C F3C . 1.374(5) ?
C19C H19C . 0.980 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_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
N3A H3A3 O1A . . 1_554 0.90 2.58 3.176(4) 125 yes
N3A H3A3 O2A . . 1_554 0.90 1.86 2.758(4) 173 yes
N3A H3A4 O2B . . 2_666 0.90 2.39 2.885(4) 114 yes
N3A H3A4 O3B . . 2_666 0.90 1.85 2.717(4) 162 yes
N3B H3B3 O1B . . 1_565 0.90 2.77 3.376(4) 126 yes
N3B H3B3 O2B . . 1_565 0.90 1.82 2.724(4) 179 yes
N3B H3B4 O2A . . 2_677 0.90 2.50 2.894(4) 107 yes
N3B H3B4 O3A . . 2_677 0.90 1.79 2.687(4) 171 yes
O4A H4A O1A . . 2_667 0.82 1.88 2.672(4) 162 yes
O4B H4B O1B . . 2_666 0.82 1.87 2.666(4) 165 yes
O4C H4C O1B . . 2_667 0.82 1.93 2.733(4) 168 yes
C2A H2A2 F3B . . 2_666 0.97 2.51 3.207(5) 128 yes
C14A H14A O2A . . 2_777 0.97 2.49 3.350(5) 148 yes
C14A H14A O3A . . 2_777 0.97 2.49 3.274(4) 138 yes
C16A H16A O4B . . 2_676 0.97 2.48 3.148(5) 126 yes
C1B H1B F2C . . . 0.98 2.45 3.200(5) 133 yes
C14B H14D O2B . . 2_666 0.97 2.34 3.295(4) 170 yes
C15B H15D O2A . . 2_677 0.97 2.51 3.131(5) 122 yes
C18B H18D F1B . . . 0.97 2.46 3.396(5) 161 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
N1A C1A C2A C3A . . . . 107.0(4) ?
N1A C1A C3A C2A . . . . -108.3(4) ?
N1A C5A C6A C8A . . . . 2.1(6) ?
N1A C5A C6A C7A . . . . -179.9(4) ?
C5A C6A C7A O2A . . . . 175.6(4) ?
C8A C6A C7A O2A . . . . -6.5(6) ?
C5A C6A C7A O1A . . . . -3.0(5) ?
C8A C6A C7A O1A . . . . 174.9(4) ?
C5A C6A C8A O3A . . . . 173.2(4) ?
C7A C6A C8A O3A . . . . -4.7(6) ?
C5A C6A C8A C9A . . . . -7.3(5) ?
C7A C6A C8A C9A . . . . 174.8(3) ?
C17A C4A C9A C10A . . . . -1.0(5) ?
N1A C4A C9A C10A . . . . 179.6(3) ?
C17A C4A C9A C8A . . . . 177.8(3) ?
N1A C4A C9A C8A . . . . -1.6(5) ?
O3A C8A C9A C4A . . . . -173.2(3) ?
C6A C8A C9A C4A . . . . 7.2(5) ?
O3A C8A C9A C10A . . . . 5.5(5) ?
C6A C8A C9A C10A . . . . -174.0(3) ?
C4A C9A C10A C11A . . . . -0.8(5) ?
C8A C9A C10A C11A . . . . -179.6(3) ?
C9A C10A C11A F1A . . . . -175.4(3) ?
C9A C10A C11A C12A . . . . 2.2(6) ?
C10A C11A C12A C17A . . . . -1.6(6) ?
F1A C11A C12A C17A . . . . 175.9(3) ?
C10A C11A C12A N2A . . . . -178.7(4) ?
F1A C11A C12A N2A . . . . -1.2(5) ?
N2A C13A C14A N3A . . . . -55.0(4) ?
N3A C15A C16A N2A . . . . 58.8(4) ?
N2A C12A C17A C4A . . . . 176.7(3) ?
C11A C12A C17A C4A . . . . -0.2(5) ?
C9A C4A C17A C12A . . . . 1.5(6) ?
N1A C4A C17A C12A . . . . -179.1(3) ?
C6A C5A N1A C4A . . . . 4.1(6) ?
C6A C5A N1A C1A . . . . -173.7(4) ?
C9A C4A N1A C5A . . . . -4.2(5) ?
C17A C4A N1A C5A . . . . 176.4(3) ?
C9A C4A N1A C1A . . . . 173.7(3) ?
C17A C4A N1A C1A . . . . -5.8(5) ?
C2A C1A N1A C5A . . . . 37.9(5) ?
C3A C1A N1A C5A . . . . 106.8(4) ?
C2A C1A N1A C4A . . . . -139.9(4) ?
C3A C1A N1A C4A . . . . -71.0(5) ?
C17A C12A N2A C13A . . . . -9.3(5) ?
C11A C12A N2A C13A . . . . 167.6(3) ?
C17A C12A N2A C16A . . . . 125.2(4) ?
C11A C12A N2A C16A . . . . -58.0(4) ?
C14A C13A N2A C12A . . . . -163.6(3) ?
C14A C13A N2A C16A . . . . 59.7(4) ?
C15A C16A N2A C12A . . . . 159.8(3) ?
C15A C16A N2A C13A . . . . -62.4(4) ?
C13A C14A N3A C15A . . . . 53.0(4) ?
C16A C15A N3A C14A . . . . -54.6(4) ?
N1B C1B C2B C3B . . . . -105.9(4) ?
N1B C1B C3B C2B . . . . 112.2(4) ?
N1B C5B C6B C8B . . . . -0.5(6) ?
N1B C5B C6B C7B . . . . -179.9(4) ?
C5B C6B C7B O2B . . . . -179.6(3) ?
C8B C6B C7B O2B . . . . 1.0(6) ?
C5B C6B C7B O1B . . . . 0.3(5) ?
C8B C6B C7B O1B . . . . -179.0(3) ?
C5B C6B C8B O3B . . . . -179.3(4) ?
C7B C6B C8B O3B . . . . 0.0(6) ?
C5B C6B C8B C9B . . . . 1.2(5) ?
C7B C6B C8B C9B . . . . -179.4(3) ?
C17B C4B C9B C10B . . . . 0.3(5) ?
N1B C4B C9B C10B . . . . -179.7(3) ?
C17B C4B C9B C8B . . . . -179.1(3) ?
N1B C4B C9B C8B . . . . 0.9(5) ?
O3B C8B C9B C4B . . . . 179.1(3) ?
C6B C8B C9B C4B . . . . -1.4(5) ?
O3B C8B C9B C10B . . . . -0.4(5) ?
C6B C8B C9B C10B . . . . 179.1(3) ?
C4B C9B C10B C11B . . . . 0.6(5) ?
C8B C9B C10B C11B . . . . -179.9(3) ?
C9B C10B C11B F1B . . . . 176.5(3) ?
C9B C10B C11B C12B . . . . -1.0(6) ?
C10B C11B C12B C17B . . . . 0.4(6) ?
F1B C11B C12B C17B . . . . -177.1(3) ?
C10B C11B C12B N2B . . . . 177.7(4) ?
F1B C11B C12B N2B . . . . 0.3(5) ?
N2B C13B C14B N3B . . . . 56.2(4) ?
N3B C15B C16B N2B . . . . -59.4(4) ?
C9B C4B C17B C12B . . . . -0.9(6) ?
N1B C4B C17B C12B . . . . 179.1(3) ?
N2B C12B C17B C4B . . . . -176.7(3) ?
C11B C12B C17B C4B . . . . 0.5(5) ?
C6B C5B N1B C4B . . . . -0.1(6) ?
C6B C5B N1B C1B . . . . 176.9(4) ?
C17B C4B N1B C5B . . . . 180.0(3) ?
C9B C4B N1B C5B . . . . -0.1(5) ?
C17B C4B N1B C1B . . . . 2.8(5) ?
C9B C4B N1B C1B . . . . -177.2(3) ?
C2B C1B N1B C5B . . . . -30.5(6) ?
C3B C1B N1B C5B . . . . -101.2(4) ?
C2B C1B N1B C4B . . . . 146.5(4) ?
C3B C1B N1B C4B . . . . 75.8(5) ?
C17B C12B N2B C13B . . . . 8.7(5) ?
C11B C12B N2B C13B . . . . -168.5(3) ?
C17B C12B N2B C16B . . . . -122.4(4) ?
C11B C12B N2B C16B . . . . 60.4(4) ?
C14B C13B N2B C12B . . . . 166.6(3) ?
C14B C13B N2B C16B . . . . -59.9(4) ?
C15B C16B N2B C12B . . . . -163.5(3) ?
C15B C16B N2B C13B . . . . 62.2(4) ?
C13B C14B N3B C15B . . . . -54.8(4) ?
C16B C15B N3B C14B . . . . 55.7(4) ?
O4A C18A C19A F3A . . . . -66.8(5) ?
O4A C18A C19A F2A . . . . 177.1(4) ?
O4B C18B C19B F3B . . . . -170.6(4) ?
O4B C18B C19B F2B . . . . 70.6(5) ?
O4C C18C C19C F2C . . . . 60.4(5) ?
O4C C18C C19C F3C . . . . 175.6(4) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30654290
