#------------------------------------------------------------------------------
#$Date: 2021-07-09 07:43:23 +0300 (Fri, 09 Jul 2021) $
#$Revision: 267419 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/24/2022400.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_2022400
loop_
_publ_author_name
'Żesławska, Ewa'
'Szymańska, Ewa'
'Nitek, Wojciech'
'Handzlik, Jadwiga'
_publ_section_title
;
 Crystallographic studies of piperazine derivatives of
 3-methyl-5-spirofluorenehydantoin in search of structural features of
 P-gp inhibitors
;
_journal_coeditor_code           KY3205
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first
;
;
_journal_paper_doi               10.1107/S2053229621006756
_journal_volume                  77
_journal_year                    2021
_chemical_formula_iupac          'C29 H32 N4 O2 2+, 2Cl -, H2 O'
_chemical_formula_moiety         'C29 H32 N4 O2 2+, 2(Cl -), H2 O'
_chemical_formula_sum            'C29 H34 Cl2 N4 O3'
_chemical_formula_weight         557.5
_chemical_name_systematic
'1-[3-(3'-Methyl-2',4'-dioxospiro[fluorene-9,5'-imidazolidin]-1'-yl)propyl]-4-phenylpiperazine-1,4-diium dichloride monohydrate'
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 98.6980(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.96450(10)
_cell_length_b                   33.81110(10)
_cell_length_c                   9.22370(10)
_cell_measurement_reflns_used    52853
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      76.217
_cell_measurement_theta_min      2.616
_cell_volume                     2763.55(4)
_computing_cell_refinement
;
CrysAlis PRO (Rigaku OD, 2018)
;
_computing_data_collection
;
CrysAlis PRO (Rigaku OD, 2018)
;
_computing_data_reduction
;
CrysAlis PRO (Rigaku OD, 2018)
;
_computing_molecular_graphics
;
Mercury (Macrae et al., 2020)
;
_computing_publication_material
;
publCIF (Westrip, 2010)
;
_computing_structure_refinement
;
SIR2014 (Burla et al., 2015) and SHELXL2018 (Sheldrick,
2015b)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy Dualflex HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0402
_diffrn_reflns_av_unetI/netI     0.0553
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       42
_diffrn_reflns_limit_k_min       -42
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            82562
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.768
_diffrn_reflns_theta_min         2.614
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    2.419
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.538
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
(CrysAlis PRO; Rigaku OD, 2018)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.34
_exptl_crystal_description       block
_exptl_crystal_F_000             1176
_exptl_crystal_size_max          0.175
_exptl_crystal_size_mid          0.116
_exptl_crystal_size_min          0.063
_refine_diff_density_max         0.686
_refine_diff_density_min         -0.369
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.07
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     352
_refine_ls_number_reflns         5743
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.0356
_refine_ls_R_factor_gt           0.034
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0488P)²+1.4194P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.093
_refine_ls_wR_factor_ref         0.0943
_reflns_number_gt                5436
_reflns_number_total             5743
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ky3205sup1.cif
_cod_data_source_block           1
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2022400
_shelx_estimated_absorpt_t_min   0.677
_shelx_estimated_absorpt_t_max   0.863
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
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
C C14 0.92416(15) 0.16437(4) 0.96487(14) 0.0181(3) Uani d 1 . .
C C15 0.84624(15) 0.13821(4) 1.04108(15) 0.0208(3) Uani d 1 . .
H H15 0.76369 0.123361 0.992094 0.025 Uiso calc 1 . .
C C16 0.89216(17) 0.13418(4) 1.19219(16) 0.0235(3) Uani d 1 . .
H H16 0.840179 0.116416 1.246804 0.028 Uiso calc 1 . .
C C17 1.01333(17) 0.15596(4) 1.26315(15) 0.0247(3) Uani d 1 . .
H H17 1.043028 0.152807 1.365804 0.03 Uiso calc 1 . .
C C18 1.09202(16) 0.18234(4) 1.18634(15) 0.0225(3) Uani d 1 . .
H H18 1.174393 0.197232 1.235382 0.027 Uiso calc 1 . .
C C19 1.04661(15) 0.18625(4) 1.03593(15) 0.0191(3) Uani d 1 . .
C C20 1.10968(15) 0.21003(4) 0.92608(15) 0.0188(3) Uani d 1 . .
C C21 1.23306(16) 0.23540(4) 0.94024(16) 0.0223(3) Uani d 1 . .
H H21 1.289624 0.240788 1.033786 0.027 Uiso calc 1 . .
C C22 1.27186(16) 0.25276(4) 0.81409(17) 0.0245(3) Uani d 1 . .
H H22 1.354979 0.270477 0.822336 0.029 Uiso calc 1 . .
C C23 1.19126(16) 0.24465(4) 0.67639(16) 0.0233(3) Uani d 1 . .
H H23 1.220821 0.256409 0.591607 0.028 Uiso calc 1 . .
C C24 1.06689(16) 0.21927(4) 0.66229(15) 0.0203(3) Uani d 1 . .
H H24 1.011147 0.21355 0.56865 0.024 Uiso calc 1 . .
C C25 1.02691(15) 0.20265(4) 0.78810(15) 0.0182(3) Uani d 1 . .
C C5 0.89401(15) 0.17550(4) 0.80305(14) 0.0177(3) Uani d 1 . .
C C4 0.74489(15) 0.19889(4) 0.76523(14) 0.0185(3) Uani d 1 . .
N N3 0.66566(13) 0.18135(3) 0.64444(13) 0.0202(2) Uani d 1 . .
C C2 0.74346(15) 0.14874(4) 0.59755(15) 0.0194(3) Uani d 1 . .
N N1 0.86996(13) 0.14342(3) 0.69669(12) 0.0187(2) Uani d 1 . .
O O4 0.70709(11) 0.22761(3) 0.82960(11) 0.0235(2) Uani d 1 . .
C C26 0.51580(16) 0.19307(4) 0.57351(17) 0.0259(3) Uani d 1 . .
H H26A 0.480176 0.215425 0.626584 0.039 Uiso calc 1 . .
H H26B 0.446078 0.170771 0.574288 0.039 Uiso calc 1 . .
H H26C 0.520378 0.200882 0.471965 0.039 Uiso calc 1 . .
O O2 0.70114(11) 0.12952(3) 0.48774(11) 0.0242(2) Uani d 1 . .
C C6 0.98429(15) 0.11395(4) 0.67694(15) 0.0200(3) Uani d 1 . .
H H6A 1.084605 0.123997 0.721269 0.024 Uiso calc 1 . .
H H6B 0.98577 0.110218 0.570709 0.024 Uiso calc 1 . .
C C7 0.95679(15) 0.07389(4) 0.74586(15) 0.0206(3) Uani d 1 . .
H H7A 1.042754 0.056039 0.738032 0.025 Uiso calc 1 . .
H H7B 0.950398 0.077575 0.851224 0.025 Uiso calc 1 . .
C C8 0.81165(16) 0.05510(4) 0.66982(15) 0.0220(3) Uani d 1 . .
H H8A 0.728114 0.074371 0.666956 0.026 Uiso calc 1 . .
H H8B 0.823019 0.048608 0.567403 0.026 Uiso calc 1 . .
N N2 0.77203(13) 0.01816(3) 0.74610(13) 0.0194(2) Uani d 1 . .
C C10 0.61729(15) 0.00425(4) 0.68391(16) 0.0213(3) Uani d 1 . .
H H10A 0.615485 -0.00368 0.580346 0.026 Uiso calc 1 . .
H H10B 0.544313 0.026127 0.686421 0.026 Uiso calc 1 . .
C C11 0.57137(15) -0.03058(4) 0.77098(16) 0.0219(3) Uani d 1 . .
H H11A 0.564581 -0.021967 0.872365 0.026 Uiso calc 1 . .
H H11B 0.470446 -0.040036 0.725862 0.026 Uiso calc 1 . .
N N4 0.68333(13) -0.06389(3) 0.77508(13) 0.0192(2) Uani d 1 . .
C C13 0.84061(15) -0.04964(4) 0.82970(16) 0.0208(3) Uani d 1 . .
H H13A 0.913079 -0.071476 0.824124 0.025 Uiso calc 1 . .
H H13B 0.847725 -0.041546 0.933672 0.025 Uiso calc 1 . .
C C12 0.88168(15) -0.01493(4) 0.73938(16) 0.0210(3) Uani d 1 . .
H H12A 0.985032 -0.005792 0.777774 0.025 Uiso calc 1 . .
H H12B 0.879759 -0.023281 0.636244 0.025 Uiso calc 1 . .
C C27 0.63582(15) -0.09757(4) 0.85999(15) 0.0199(3) Uani d 1 . .
C C28 0.56547(17) -0.12877(4) 0.78161(16) 0.0251(3) Uani d 1 . .
H H28 0.551822 -0.128805 0.677443 0.03 Uiso calc 1 . .
C C29 0.51484(18) -0.16021(5) 0.85816(18) 0.0299(3) Uani d 1 . .
H H29 0.46628 -0.182038 0.805974 0.036 Uiso calc 1 . .
C C30 0.53466(17) -0.15993(4) 1.00974(17) 0.0277(3) Uani d 1 . .
H H30 0.50114 -0.181735 1.06124 0.033 Uiso calc 1 . .
C C31 0.60319(18) -0.12799(5) 1.08673(17) 0.0293(3) Uani d 1 . .
H H31 0.615575 -0.127776 1.190854 0.035 Uiso calc 1 . .
C C32 0.65391(18) -0.09620(5) 1.01184(16) 0.0272(3) Uani d 1 . .
H H32 0.700006 -0.074011 1.063674 0.033 Uiso calc 1 . .
O O1W 0.77434(15) -0.00116(4) 0.37870(13) 0.0389(3) Uani d 1 . .
H H2W 0.767082 0.007945 0.280568 0.058 Uiso d 1 . .
H H1W 0.742038 -0.027502 0.391083 0.058 Uiso d 1 . .
Cl Cl1 0.75787(4) 0.03266(2) 1.06444(4) 0.02518(10) Uani d 1 . .
Cl Cl2 0.67675(4) -0.08565(2) 0.45311(4) 0.02638(10) Uani d 1 . .
H H2N 0.773(2) 0.0243(5) 0.847(2) 0.031(5) Uiso d 1 . .
H H4N 0.680(2) -0.0728(6) 0.673(2) 0.033(5) 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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.018 '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'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 1 1 0.0524
0 1 0 0.032
2 -19 1 0.0606
1 3 0 0.0506
-1 -2 0 0.053
0 -1 -1 0.0108
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
C15 C14 C19 . . 121.33(12) ?
C15 C14 C5 . . 128.87(12) ?
C19 C14 C5 . . 109.77(11) ?
C14 C15 C16 . . 118.26(13) ?
C14 C15 H15 . . 120.9 ?
C16 C15 H15 . . 120.9 ?
C17 C16 C15 . . 120.55(13) ?
C17 C16 H16 . . 119.7 ?
C15 C16 H16 . . 119.7 ?
C16 C17 C18 . . 121.22(13) ?
C16 C17 H17 . . 119.4 ?
C18 C17 H17 . . 119.4 ?
C19 C18 C17 . . 118.22(13) ?
C19 C18 H18 . . 120.9 ?
C17 C18 H18 . . 120.9 ?
C18 C19 C14 . . 120.42(13) ?
C18 C19 C20 . . 130.79(13) ?
C14 C19 C20 . . 108.76(12) ?
C21 C20 C25 . . 120.12(12) ?
C21 C20 C19 . . 130.96(13) ?
C25 C20 C19 . . 108.88(12) ?
C20 C21 C22 . . 118.49(13) ?
C20 C21 H21 . . 120.8 ?
C22 C21 H21 . . 120.8 ?
C23 C22 C21 . . 121.25(13) ?
C23 C22 H22 . . 119.4 ?
C21 C22 H22 . . 119.4 ?
C22 C23 C24 . . 120.22(13) ?
C22 C23 H23 . . 119.9 ?
C24 C23 H23 . . 119.9 ?
C25 C24 C23 . . 118.38(13) ?
C25 C24 H24 . . 120.8 ?
C23 C24 H24 . . 120.8 ?
C24 C25 C20 . . 121.51(13) ?
C24 C25 C5 . . 128.62(12) ?
C20 C25 C5 . . 109.86(11) ?
N1 C5 C14 . . 117.53(11) ?
N1 C5 C25 . . 115.15(11) ?
C14 C5 C25 . . 102.23(10) ?
N1 C5 C4 . . 101.19(10) ?
C14 C5 C4 . . 111.50(10) ?
C25 C5 C4 . . 109.38(10) ?
O4 C4 N3 . . 126.79(13) ?
O4 C4 C5 . . 126.49(12) ?
N3 C4 C5 . . 106.71(11) ?
C4 N3 C2 . . 111.77(11) ?
C4 N3 C26 . . 125.43(12) ?
C2 N3 C26 . . 122.75(11) ?
O2 C2 N1 . . 127.93(13) ?
O2 C2 N3 . . 124.65(13) ?
N1 C2 N3 . . 107.42(11) ?
C2 N1 C5 . . 112.25(11) ?
C2 N1 C6 . . 122.49(11) ?
C5 N1 C6 . . 123.85(11) ?
N3 C26 H26A . . 109.5 ?
N3 C26 H26B . . 109.5 ?
H26A C26 H26B . . 109.5 ?
N3 C26 H26C . . 109.5 ?
H26A C26 H26C . . 109.5 ?
H26B C26 H26C . . 109.5 ?
N1 C6 C7 . . 113.05(11) ?
N1 C6 H6A . . 109 ?
C7 C6 H6A . . 109 ?
N1 C6 H6B . . 109 ?
C7 C6 H6B . . 109 ?
H6A C6 H6B . . 107.8 ?
C8 C7 C6 . . 110.98(11) ?
C8 C7 H7A . . 109.4 ?
C6 C7 H7A . . 109.4 ?
C8 C7 H7B . . 109.4 ?
C6 C7 H7B . . 109.4 ?
H7A C7 H7B . . 108 ?
N2 C8 C7 . . 112.19(11) ?
N2 C8 H8A . . 109.2 ?
C7 C8 H8A . . 109.2 ?
N2 C8 H8B . . 109.2 ?
C7 C8 H8B . . 109.2 ?
H8A C8 H8B . . 107.9 ?
C10 N2 C12 . . 109.04(10) ?
C10 N2 C8 . . 110.68(10) ?
C12 N2 C8 . . 113.51(11) ?
C10 N2 H2N . . 108.3(12) ?
C12 N2 H2N . . 107.1(11) ?
C8 N2 H2N . . 108.0(11) ?
N2 C10 C11 . . 110.58(11) ?
N2 C10 H10A . . 109.5 ?
C11 C10 H10A . . 109.5 ?
N2 C10 H10B . . 109.5 ?
C11 C10 H10B . . 109.5 ?
H10A C10 H10B . . 108.1 ?
N4 C11 C10 . . 111.15(11) ?
N4 C11 H11A . . 109.4 ?
C10 C11 H11A . . 109.4 ?
N4 C11 H11B . . 109.4 ?
C10 C11 H11B . . 109.4 ?
H11A C11 H11B . . 108 ?
C27 N4 C13 . . 113.55(10) ?
C27 N4 C11 . . 110.17(10) ?
C13 N4 C11 . . 110.89(10) ?
C27 N4 H4N . . 107.5(11) ?
C13 N4 H4N . . 108.2(11) ?
C11 N4 H4N . . 106.3(11) ?
N4 C13 C12 . . 110.94(11) ?
N4 C13 H13A . . 109.5 ?
C12 C13 H13A . . 109.5 ?
N4 C13 H13B . . 109.5 ?
C12 C13 H13B . . 109.5 ?
H13A C13 H13B . . 108 ?
N2 C12 C13 . . 109.89(11) ?
N2 C12 H12A . . 109.7 ?
C13 C12 H12A . . 109.7 ?
N2 C12 H12B . . 109.7 ?
C13 C12 H12B . . 109.7 ?
H12A C12 H12B . . 108.2 ?
C28 C27 C32 . . 122.05(13) ?
C28 C27 N4 . . 117.20(12) ?
C32 C27 N4 . . 120.64(12) ?
C27 C28 C29 . . 118.56(14) ?
C27 C28 H28 . . 120.7 ?
C29 C28 H28 . . 120.7 ?
C30 C29 C28 . . 120.45(14) ?
C30 C29 H29 . . 119.8 ?
C28 C29 H29 . . 119.8 ?
C29 C30 C31 . . 120.21(14) ?
C29 C30 H30 . . 119.9 ?
C31 C30 H30 . . 119.9 ?
C30 C31 C32 . . 120.08(14) ?
C30 C31 H31 . . 120 ?
C32 C31 H31 . . 120 ?
C27 C32 C31 . . 118.62(14) ?
C27 C32 H32 . . 120.7 ?
C31 C32 H32 . . 120.7 ?
H2W O1W H1W . . 116.2 ?
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
C14 C15 . 1.3832(19) ?
C14 C19 . 1.4015(19) ?
C14 C5 . 1.5233(18) ?
C15 C16 . 1.399(2) ?
C15 H15 . 0.95 ?
C16 C17 . 1.391(2) ?
C16 H16 . 0.95 ?
C17 C18 . 1.395(2) ?
C17 H17 . 0.95 ?
C18 C19 . 1.3918(19) ?
C18 H18 . 0.95 ?
C19 C20 . 1.4718(18) ?
C20 C21 . 1.3902(19) ?
C20 C25 . 1.3953(19) ?
C21 C22 . 1.393(2) ?
C21 H21 . 0.95 ?
C22 C23 . 1.390(2) ?
C22 H22 . 0.95 ?
C23 C24 . 1.397(2) ?
C23 H23 . 0.95 ?
C24 C25 . 1.3844(19) ?
C24 H24 . 0.95 ?
C25 C5 . 1.5266(18) ?
C5 N1 . 1.4566(16) ?
C5 C4 . 1.5470(18) ?
C4 O4 . 1.2129(16) ?
C4 N3 . 1.3632(18) ?
N3 C2 . 1.4072(17) ?
N3 C26 . 1.4573(17) ?
C2 O2 . 1.2148(17) ?
C2 N1 . 1.3568(18) ?
N1 C6 . 1.4605(16) ?
C26 H26A . 0.98 ?
C26 H26B . 0.98 ?
C26 H26C . 0.98 ?
C6 C7 . 1.5320(18) ?
C6 H6A . 0.99 ?
C6 H6B . 0.99 ?
C7 C8 . 1.5207(19) ?
C7 H7A . 0.99 ?
C7 H7B . 0.99 ?
C8 N2 . 1.5023(17) ?
C8 H8A . 0.99 ?
C8 H8B . 0.99 ?
N2 C10 . 1.4945(17) ?
N2 C12 . 1.4966(17) ?
N2 H2N . 0.95(2) ?
C10 C11 . 1.5169(19) ?
C10 H10A . 0.99 ?
C10 H10B . 0.99 ?
C11 N4 . 1.5054(17) ?
C11 H11A . 0.99 ?
C11 H11B . 0.99 ?
N4 C27 . 1.4808(17) ?
N4 C13 . 1.5031(17) ?
N4 H4N . 0.98(2) ?
C13 C12 . 1.5163(18) ?
C13 H13A . 0.99 ?
C13 H13B . 0.99 ?
C12 H12A . 0.99 ?
C12 H12B . 0.99 ?
C27 C28 . 1.377(2) ?
C27 C32 . 1.386(2) ?
C28 C29 . 1.390(2) ?
C28 H28 . 0.95 ?
C29 C30 . 1.383(2) ?
C29 H29 . 0.95 ?
C30 C31 . 1.384(2) ?
C30 H30 . 0.95 ?
C31 C32 . 1.391(2) ?
C31 H31 . 0.95 ?
C32 H32 . 0.95 ?
O1W H2W . 0.9489 ?
O1W H1W . 0.9488 ?
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
N2 H2N Cl1 . 0.95(2) 2.05(2) 2.9990(10) 174(2) yes
N4 H4N Cl2 . 0.98(2) 2.07(2) 3.0510(10) 174(2) yes
C8 H8A O2 . 0.99 2.48 3.103(2) 120.7 yes
C8 H8B O1W . 0.99 2.41 3.266(2) 144 yes
C10 H10A O1W . 0.99 2.51 3.338(2) 141.1 yes
C10 H10B Cl2 3_656 0.99 2.98 3.8870(10) 153.4 yes
C11 H11A Cl1 . 0.99 2.94 3.650(2) 129.8 yes
C11 H11B O1W 3_656 0.99 2.65 3.372(2) 129.5 yes
C12 H12A Cl1 3_757 0.99 2.69 3.5080(10) 140.1 yes
C12 H12B O1W . 0.99 2.53 3.353(2) 140.1 yes
C13 H13B Cl1 . 0.99 2.95 3.6700(10) 130.5 yes
C28 H28 O2 3_656 0.95 2.53 3.176(2) 125.1 yes
C28 H28 Cl2 . 0.95 2.89 3.635(2) 135.9 yes
O1W H2W Cl1 1_554 0.95 2.15 3.0990(10) 175.8 yes
O1W H1W Cl2 . 0.95 2.15 3.0950(10) 171.6 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
C19 C14 C15 C16 . . . . 0.35(19) ?
C5 C14 C15 C16 . . . . -177.28(12) ?
C14 C15 C16 C17 . . . . -0.1(2) ?
C15 C16 C17 C18 . . . . 0.1(2) ?
C16 C17 C18 C19 . . . . -0.3(2) ?
C17 C18 C19 C14 . . . . 0.5(2) ?
C17 C18 C19 C20 . . . . -177.31(13) ?
C15 C14 C19 C18 . . . . -0.6(2) ?
C5 C14 C19 C18 . . . . 177.48(12) ?
C15 C14 C19 C20 . . . . 177.70(12) ?
C5 C14 C19 C20 . . . . -4.26(14) ?
C18 C19 C20 C21 . . . . 0.2(2) ?
C14 C19 C20 C21 . . . . -177.82(14) ?
C18 C19 C20 C25 . . . . 177.72(14) ?
C14 C19 C20 C25 . . . . -0.29(15) ?
C25 C20 C21 C22 . . . . -0.5(2) ?
C19 C20 C21 C22 . . . . 176.77(13) ?
C20 C21 C22 C23 . . . . -1.0(2) ?
C21 C22 C23 C24 . . . . 1.2(2) ?
C22 C23 C24 C25 . . . . 0.0(2) ?
C23 C24 C25 C20 . . . . -1.50(19) ?
C23 C24 C25 C5 . . . . 177.56(12) ?
C21 C20 C25 C24 . . . . 1.8(2) ?
C19 C20 C25 C24 . . . . -176.06(12) ?
C21 C20 C25 C5 . . . . -177.44(12) ?
C19 C20 C25 C5 . . . . 4.72(14) ?
C15 C14 C5 N1 . . . . -48.36(19) ?
C19 C14 C5 N1 . . . . 133.79(12) ?
C15 C14 C5 C25 . . . . -175.47(13) ?
C19 C14 C5 C25 . . . . 6.68(13) ?
C15 C14 C5 C4 . . . . 67.77(17) ?
C19 C14 C5 C4 . . . . -110.08(12) ?
C24 C25 C5 N1 . . . . 45.36(18) ?
C20 C25 C5 N1 . . . . -135.50(12) ?
C24 C25 C5 C14 . . . . 173.98(13) ?
C20 C25 C5 C14 . . . . -6.88(13) ?
C24 C25 C5 C4 . . . . -67.74(17) ?
C20 C25 C5 C4 . . . . 111.40(12) ?
N1 C5 C4 O4 . . . . 175.98(13) ?
C14 C5 C4 O4 . . . . 50.23(17) ?
C25 C5 C4 O4 . . . . -62.10(17) ?
N1 C5 C4 N3 . . . . -4.96(13) ?
C14 C5 C4 N3 . . . . -130.71(11) ?
C25 C5 C4 N3 . . . . 116.96(12) ?
O4 C4 N3 C2 . . . . 179.58(13) ?
C5 C4 N3 C2 . . . . 0.52(14) ?
O4 C4 N3 C26 . . . . -2.9(2) ?
C5 C4 N3 C26 . . . . 178.02(12) ?
C4 N3 C2 O2 . . . . -175.58(13) ?
C26 N3 C2 O2 . . . . 6.8(2) ?
C4 N3 C2 N1 . . . . 4.60(15) ?
C26 N3 C2 N1 . . . . -172.97(12) ?
O2 C2 N1 C5 . . . . 171.99(13) ?
N3 C2 N1 C5 . . . . -8.20(15) ?
O2 C2 N1 C6 . . . . 5.1(2) ?
N3 C2 N1 C6 . . . . -175.11(11) ?
C14 C5 N1 C2 . . . . 129.72(12) ?
C25 C5 N1 C2 . . . . -109.72(13) ?
C4 C5 N1 C2 . . . . 8.09(14) ?
C14 C5 N1 C6 . . . . -63.58(16) ?
C25 C5 N1 C6 . . . . 56.99(16) ?
C4 C5 N1 C6 . . . . 174.79(11) ?
C2 N1 C6 C7 . . . . -91.18(15) ?
C5 N1 C6 C7 . . . . 103.44(14) ?
N1 C6 C7 C8 . . . . 64.84(15) ?
C6 C7 C8 N2 . . . . -173.22(11) ?
C7 C8 N2 C10 . . . . 170.67(11) ?
C7 C8 N2 C12 . . . . -66.34(15) ?
C12 N2 C10 C11 . . . . 60.15(14) ?
C8 N2 C10 C11 . . . . -174.31(11) ?
N2 C10 C11 N4 . . . . -56.83(15) ?
C10 C11 N4 C27 . . . . -179.75(11) ?
C10 C11 N4 C13 . . . . 53.68(15) ?
C27 N4 C13 C12 . . . . -179.40(11) ?
C11 N4 C13 C12 . . . . -54.72(14) ?
C10 N2 C12 C13 . . . . -60.93(14) ?
C8 N2 C12 C13 . . . . 175.18(11) ?
N4 C13 C12 N2 . . . . 58.67(14) ?
C13 N4 C27 C28 . . . . -134.47(13) ?
C11 N4 C27 C28 . . . . 100.48(14) ?
C13 N4 C27 C32 . . . . 49.37(17) ?
C11 N4 C27 C32 . . . . -75.69(16) ?
C32 C27 C28 C29 . . . . -1.7(2) ?
N4 C27 C28 C29 . . . . -177.79(13) ?
C27 C28 C29 C30 . . . . 0.2(2) ?
C28 C29 C30 C31 . . . . 1.0(2) ?
C29 C30 C31 C32 . . . . -0.7(2) ?
C28 C27 C32 C31 . . . . 2.0(2) ?
N4 C27 C32 C31 . . . . 177.94(13) ?
C30 C31 C32 C27 . . . . -0.7(2) ?

_cod_database_fobs_code 2022400
