#------------------------------------------------------------------------------
#$Date: 2023-07-05 14:02:33 +0300 (Wed, 05 Jul 2023) $
#$Revision: 284977 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/68/7246847.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_7246847
loop_
_publ_author_name
'Mojzych, Ilona'
'Zawadzka, Anna'
'Kaczyńska, Katarzyna'
'Wojciechowski, Piotr'
'Zając, Dominika'
'Chotkowski, Maciej'
'Wiktorska, Katarzyna'
'Maurin, Jan K.'
'Mazur, Maciej'
_publ_section_title
;
 A tetrahydroacridine derivative and its conjugate with gold
 nanoparticles: promising agents for the treatment of Alzheimer's disease.
;
_journal_issue                   25
_journal_name_full               'Physical chemistry chemical physics : PCCP'
_journal_page_first              16796
_journal_page_last               16806
_journal_paper_doi               10.1039/d3cp00767g
_journal_volume                  25
_journal_year                    2023
_chemical_formula_moiety         '(C15 H17 Cl N3)^+^, Cl^-^, 2(H2 O)'
_chemical_formula_sum            'C15 H21 Cl2 N3 O2'
_chemical_formula_weight         346.25
_chemical_melting_point          393
_chemical_name_systematic
'6-chloro-1,2,3,4,9,10,11,12-octahydro- [1,4]-diazepine-[5,6,7-kl]-acridine  monohydrochloride dihydrate'
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_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           SHELXL-97
_audit_update_record
;
2022-07-06 deposited with the CCDC.	2023-05-29 downloaded from the CCDC.
;
_cell_angle_alpha                111.519(6)
_cell_angle_beta                 96.992(5)
_cell_angle_gamma                92.865(6)
_cell_formula_units_Z            2
_cell_length_a                   7.0963(5)
_cell_length_b                   9.7638(7)
_cell_length_c                   12.7882(7)
_cell_measurement_reflns_used    2853
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      69.7954
_cell_measurement_theta_min      3.7553
_cell_volume                     813.85(10)
_computing_cell_refinement
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
(compiled Apr 28 2010,14:27:37)
;
_computing_data_collection
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
(compiled Apr 28 2010,14:27:37)
;
_computing_data_reduction
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
(compiled Apr 28 2010,14:27:37)
;
_computing_molecular_graphics
;
 X-Seed - A Software Tool for Supramolecular Crystallography. L.J. Barbour, 
 J. Supramol.  Chem. 2001, 1, 189-191, doi:10.1016/S1472-7862(02)00030-8.
 ShelXle: A  graphical user interface for SHELXL. C.B.Hübschle, G.M.Sheldrick,
 B.Dittrich, J. Appl. Cryst. 2011, 44, 1281-1284, doi:10.1107/S0021889811043202.
;
_computing_publication_material
;
 XL- CRYSTAL STRUCTURE REFINEMENT - SHELXTL Ver. 6.12 W95/98/NT/2000/ME,
 Bruker-AXS
;
_computing_structure_refinement
;
 XL- CRYSTAL STRUCTURE REFINEMENT - SHELXTL Ver.6.12 W95/98/NT/2000/ME, 
 Bruker-AXS
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 10.4922
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'Xcalibur, Ruby'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Cu) X-ray Source'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0764
_diffrn_reflns_av_sigmaI/netI    0.0824
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            14996
_diffrn_reflns_theta_full        69.92
_diffrn_reflns_theta_max         69.92
_diffrn_reflns_theta_min         3.76
_exptl_absorpt_coefficient_mu    3.679
_exptl_absorpt_correction_T_max  0.924
_exptl_absorpt_correction_T_min  0.691
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
(compiled Apr 28 2010,14:27:37)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.413
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             364
_exptl_crystal_size_max          0.1914
_exptl_crystal_size_mid          0.0456
_exptl_crystal_size_min          0.0246
_refine_diff_density_max         0.245
_refine_diff_density_min         -0.204
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       0.0016(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.762
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     221
_refine_ls_number_reflns         3030
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.762
_refine_ls_R_factor_all          0.0880
_refine_ls_R_factor_gt           0.0364
_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)+(0.0366P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0702
_refine_ls_wR_factor_ref         0.0791
_reflns_number_gt                1579
_reflns_number_total             3030
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d3cp00767g2.cif
_cod_data_source_block           zc205abs
_cod_depositor_comments          'Adding full bibliography for 7246847.cif.'
_cod_original_cell_volume        813.85(9)
_cod_database_code               7246847
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.24432(12) 0.83252(8) 1.21904(6) 0.0625(2) Uani 1 1 d . . .
N1 N 0.2129(3) 0.8287(2) 0.82276(17) 0.0437(6) Uani 1 1 d . . .
H1 H 0.198(4) 0.734(3) 0.807(2) 0.052 Uiso 1 1 d . . .
C2 C 0.2203(4) 0.8832(3) 0.7412(2) 0.0399(6) Uani 1 1 d . . .
C3 C 0.2056(5) 0.7717(3) 0.6228(2) 0.0594(8) Uani 1 1 d . . .
H3A H 0.1063 0.6934 0.6110 0.071 Uiso 1 1 calc R . .
H3B H 0.3252 0.7280 0.6132 0.071 Uiso 1 1 calc R . .
C4 C 0.1609(5) 0.8389(3) 0.5343(2) 0.0760(10) Uani 1 1 d . . .
H4A H 0.1852 0.7708 0.4612 0.091 Uiso 1 1 calc R . .
H4B H 0.0268 0.8545 0.5273 0.091 Uiso 1 1 calc R . .
C5 C 0.2767(5) 0.9800(3) 0.5646(2) 0.0673(9) Uani 1 1 d . . .
H5A H 0.2482 1.0177 0.5047 0.081 Uiso 1 1 calc R . .
H5B H 0.4106 0.9635 0.5700 0.081 Uiso 1 1 calc R . .
C6 C 0.2418(4) 1.0953(3) 0.6765(2) 0.0484(7) Uani 1 1 d . . .
H6A H 0.3418 1.1767 0.7015 0.058 Uiso 1 1 calc R . .
H6B H 0.1212 1.1340 0.6647 0.058 Uiso 1 1 calc R . .
C7 C 0.2372(4) 1.0332(3) 0.7684(2) 0.0387(6) Uani 1 1 d . . .
C8 C 0.2429(3) 1.1304(2) 0.8838(2) 0.0365(6) Uani 1 1 d . . .
C9 C 0.2608(3) 1.0721(2) 0.97286(19) 0.0353(6) Uani 1 1 d . . .
C10 C 0.2948(4) 1.1511(3) 1.0939(2) 0.0414(6) Uani 1 1 d . . .
C11 C 0.2830(4) 1.0738(3) 1.1666(2) 0.0464(7) Uani 1 1 d . . .
H11 H 0.2965 1.1259 1.2447 0.056 Uiso 1 1 calc R . .
C12 C 0.2519(4) 0.9220(3) 1.1238(2) 0.0436(7) Uani 1 1 d . . .
C13 C 0.2318(4) 0.8405(3) 1.0111(2) 0.0416(6) Uani 1 1 d . . .
H13 H 0.2161 0.7377 0.9841 0.050 Uiso 1 1 calc R . .
C14 C 0.2351(4) 0.9138(2) 0.9365(2) 0.0373(6) Uani 1 1 d . . .
N15 N 0.2317(3) 1.2733(2) 0.90178(18) 0.0460(6) Uani 1 1 d . . .
H15 H 0.216(4) 1.299(3) 0.846(2) 0.055 Uiso 1 1 d . . .
C16 C 0.2156(4) 1.3941(3) 1.0063(2) 0.0474(7) Uani 1 1 d . . .
H16A H 0.0944 1.3785 1.0300 0.057 Uiso 1 1 calc R . .
H16B H 0.2175 1.4857 0.9929 0.057 Uiso 1 1 calc R . .
C17 C 0.3733(4) 1.4079(3) 1.0987(2) 0.0545(8) Uani 1 1 d . . .
H17A H 0.4930 1.3979 1.0685 0.065 Uiso 1 1 calc R . .
H17B H 0.3817 1.5057 1.1578 0.065 Uiso 1 1 calc R . .
N18 N 0.3471(4) 1.2998(2) 1.14725(19) 0.0584(7) Uani 1 1 d . . .
H18 H 0.339(4) 1.330(3) 1.219(2) 0.070 Uiso 1 1 d . . .
Cl2 Cl 0.10635(11) 0.48162(7) 0.75409(6) 0.0579(2) Uani 1 1 d . . .
O1 O 0.2900(4) 1.4693(3) 1.37674(19) 0.0782(8) Uani 1 1 d . . .
H1A H 0.286(6) 1.432(4) 1.424(3) 0.117 Uiso 1 1 d . . .
H1B H 0.189(6) 1.488(5) 1.351(3) 0.117 Uiso 1 1 d . . .
O2 O 0.3503(5) 1.3592(3) 1.5469(2) 0.0981(10) Uani 1 1 d . . .
H2A H 0.288(7) 1.389(5) 1.595(4) 0.147 Uiso 1 1 d . . .
H2B H 0.451(7) 1.409(6) 1.572(4) 0.147 Uiso 1 1 d . . .
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'
N N 0.0311 0.0180 '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'
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N1 C14 124.1(2) . . ?
C2 N1 H1 121.2(17) . . ?
C14 N1 H1 114.6(16) . . ?
N1 C2 C7 120.1(2) . . ?
N1 C2 C3 116.0(2) . . ?
C7 C2 C3 123.8(2) . . ?
C2 C3 C4 112.3(2) . . ?
C2 C3 H3A 109.1 . . ?
C4 C3 H3A 109.1 . . ?
C2 C3 H3B 109.1 . . ?
C4 C3 H3B 109.1 . . ?
H3A C3 H3B 107.9 . . ?
C5 C4 C3 111.3(3) . . ?
C5 C4 H4A 109.4 . . ?
C3 C4 H4A 109.4 . . ?
C5 C4 H4B 109.4 . . ?
C3 C4 H4B 109.4 . . ?
H4A C4 H4B 108.0 . . ?
C4 C5 C6 112.7(2) . . ?
C4 C5 H5A 109.0 . . ?
C6 C5 H5A 109.0 . . ?
C4 C5 H5B 109.0 . . ?
C6 C5 H5B 109.0 . . ?
H5A C5 H5B 107.8 . . ?
C7 C6 C5 112.4(2) . . ?
C7 C6 H6A 109.1 . . ?
C5 C6 H6A 109.1 . . ?
C7 C6 H6B 109.1 . . ?
C5 C6 H6B 109.1 . . ?
H6A C6 H6B 107.8 . . ?
C2 C7 C8 119.5(2) . . ?
C2 C7 C6 120.4(2) . . ?
C8 C7 C6 120.1(2) . . ?
N15 C8 C7 116.1(2) . . ?
N15 C8 C9 124.1(2) . . ?
C7 C8 C9 119.8(2) . . ?
C14 C9 C10 115.0(2) . . ?
C14 C9 C8 116.1(2) . . ?
C10 C9 C8 128.8(2) . . ?
N18 C10 C11 115.1(2) . . ?
N18 C10 C9 125.0(2) . . ?
C11 C10 C9 119.8(2) . . ?
C12 C11 C10 120.8(2) . . ?
C12 C11 H11 119.6 . . ?
C10 C11 H11 119.6 . . ?
C13 C12 C11 122.1(2) . . ?
C13 C12 Cl1 119.4(2) . . ?
C11 C12 Cl1 118.5(2) . . ?
C12 C13 C14 118.5(2) . . ?
C12 C13 H13 120.7 . . ?
C14 C13 H13 120.7 . . ?
N1 C14 C13 117.3(2) . . ?
N1 C14 C9 119.3(2) . . ?
C13 C14 C9 123.4(2) . . ?
C8 N15 C16 128.8(2) . . ?
C8 N15 H15 119.0(18) . . ?
C16 N15 H15 111.6(18) . . ?
N15 C16 C17 111.9(2) . . ?
N15 C16 H16A 109.2 . . ?
C17 C16 H16A 109.2 . . ?
N15 C16 H16B 109.2 . . ?
C17 C16 H16B 109.2 . . ?
H16A C16 H16B 107.9 . . ?
N18 C17 C16 112.6(2) . . ?
N18 C17 H17A 109.1 . . ?
C16 C17 H17A 109.1 . . ?
N18 C17 H17B 109.1 . . ?
C16 C17 H17B 109.1 . . ?
H17A C17 H17B 107.8 . . ?
C10 N18 C17 129.0(2) . . ?
C10 N18 H18 111.4(19) . . ?
C17 N18 H18 118.3(19) . . ?
H1A O1 H1B 117(4) . . ?
H2A O2 H2B 104(5) . . ?
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
Cl1 C12 1.744(2) . ?
N1 C2 1.338(3) . ?
N1 C14 1.369(3) . ?
N1 H1 0.87(2) . ?
C2 C7 1.371(3) . ?
C2 C3 1.494(3) . ?
C3 C4 1.513(4) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C5 1.463(4) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C6 1.519(3) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 C7 1.510(3) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.426(3) . ?
C8 N15 1.336(3) . ?
C8 C9 1.444(3) . ?
C9 C14 1.435(3) . ?
C9 C10 1.437(3) . ?
C10 N18 1.367(3) . ?
C10 C11 1.403(3) . ?
C11 C12 1.374(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.352(3) . ?
C13 C14 1.388(3) . ?
C13 H13 0.9300 . ?
N15 C16 1.444(3) . ?
N15 H15 0.84(2) . ?
C16 C17 1.488(3) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 N18 1.423(3) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
N18 H18 0.87(3) . ?
O1 H1A 0.81(4) . ?
O1 H1B 0.81(4) . ?
O2 H2A 0.78(4) . ?
O2 H2B 0.80(5) . ?
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
N1 H1 Cl2 0.87(2) 2.33(3) 3.198(2) 170(2) .
N15 H15 Cl2 0.84(2) 2.57(3) 3.330(2) 151(2) 1_565
N18 H18 O1 0.87(3) 2.06(3) 2.883(3) 158(3) .
O1 H1A O2 0.81(4) 1.97(4) 2.758(4) 165(4) .
O1 H1B Cl2 0.81(4) 2.44(4) 3.243(3) 172(4) 2_577
O2 H2A Cl2 0.78(4) 2.45(4) 3.232(3) 177(5) 1_566
O2 H2B O1 0.80(5) 2.04(5) 2.835(4) 175(5) 2_688
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_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C14 N1 C2 C7 -5.0(4) . . . . ?
C14 N1 C2 C3 176.1(3) . . . . ?
N1 C2 C3 C4 164.3(3) . . . . ?
C7 C2 C3 C4 -14.6(4) . . . . ?
C2 C3 C4 C5 44.3(4) . . . . ?
C3 C4 C5 C6 -61.1(4) . . . . ?
C4 C5 C6 C7 45.2(4) . . . . ?
N1 C2 C7 C8 -1.3(4) . . . . ?
C3 C2 C7 C8 177.6(3) . . . . ?
N1 C2 C7 C6 -178.8(2) . . . . ?
C3 C2 C7 C6 0.1(4) . . . . ?
C5 C6 C7 C2 -14.6(4) . . . . ?
C5 C6 C7 C8 167.9(2) . . . . ?
C2 C7 C8 N15 -170.6(2) . . . . ?
C6 C7 C8 N15 6.9(4) . . . . ?
C2 C7 C8 C9 9.6(4) . . . . ?
C6 C7 C8 C9 -172.9(2) . . . . ?
N15 C8 C9 C14 168.8(2) . . . . ?
C7 C8 C9 C14 -11.5(3) . . . . ?
N15 C8 C9 C10 -9.0(4) . . . . ?
C7 C8 C9 C10 170.7(3) . . . . ?
C14 C9 C10 N18 171.2(3) . . . . ?
C8 C9 C10 N18 -11.0(4) . . . . ?
C14 C9 C10 C11 -6.0(4) . . . . ?
C8 C9 C10 C11 171.8(3) . . . . ?
N18 C10 C11 C12 -173.1(2) . . . . ?
C9 C10 C11 C12 4.4(4) . . . . ?
C10 C11 C12 C13 0.2(4) . . . . ?
C10 C11 C12 Cl1 178.5(2) . . . . ?
C11 C12 C13 C14 -2.7(4) . . . . ?
Cl1 C12 C13 C14 179.0(2) . . . . ?
C2 N1 C14 C13 -177.3(2) . . . . ?
C2 N1 C14 C9 2.5(4) . . . . ?
C12 C13 C14 N1 -179.5(2) . . . . ?
C12 C13 C14 C9 0.6(4) . . . . ?
C10 C9 C14 N1 -176.2(2) . . . . ?
C8 C9 C14 N1 5.7(3) . . . . ?
C10 C9 C14 C13 3.6(4) . . . . ?
C8 C9 C14 C13 -174.4(2) . . . . ?
C7 C8 N15 C16 173.5(3) . . . . ?
C9 C8 N15 C16 -6.7(4) . . . . ?
C8 N15 C16 C17 55.8(4) . . . . ?
N15 C16 C17 N18 -76.9(3) . . . . ?
C11 C10 N18 C17 179.4(3) . . . . ?
C9 C10 N18 C17 2.1(5) . . . . ?
C16 C17 N18 C10 45.9(4) . . . . ?
