#------------------------------------------------------------------------------
#$Date: 2016-03-26 14:49:08 +0100 (Sat 26 de Mar de 2016) $
#$Revision: 180317 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/31/7153199.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_7153199
loop_
_publ_author_name
'de Aquino, Roney Anderson Nascimento'
'Modolo, Luzia Valentina'
'Alves, Rosemeire Brondi'
'de Fátima, Angelo'
_publ_section_title
;
 Synthesis, kinetic studies and molecular modeling of novel tacrine dimers
 as cholinesterase inhibitors.
;
_journal_issue                   48
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              8395
_journal_page_last               8409
_journal_paper_doi               10.1039/c3ob41762j
_journal_volume                  11
_journal_year                    2013
_chemical_formula_moiety         'C32 H32 N4, 2(C4 H F6 O4)'
_chemical_formula_sum            'C40 H34 F12 N4 O8'
_chemical_formula_weight         926.71
_chemical_name_systematic
;
 ?
;
_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_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.3
_audit_creation_date             2011-09-02T09:43:15-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                100.578(3)
_cell_angle_beta                 103.072(3)
_cell_angle_gamma                96.793(3)
_cell_formula_units_Z            1
_cell_length_a                   8.7040(3)
_cell_length_b                   10.8569(3)
_cell_length_c                   11.5890(4)
_cell_measurement_reflns_used    6839
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      29.5066
_cell_measurement_theta_min      1.9314
_cell_volume                     1033.93(6)
_computing_cell_refinement       'CrysAlisPro (Oxford Diffraction Ltd., 2010)'
_computing_data_collection       'CrysAlisPro (Oxford Diffraction Ltd., 2010)'
_computing_data_reduction        'CrysAlisPro (Oxford Diffraction Ltd., 2010)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1986)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 10.4186
_diffrn_measured_fraction_theta_full 0.98
_diffrn_measured_fraction_theta_max 0.89
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.028
_diffrn_reflns_av_unetI/netI     0.0294
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            17165
_diffrn_reflns_theta_full        29.50
_diffrn_reflns_theta_max         29.57
_diffrn_reflns_theta_min         1.94
_exptl_absorpt_coefficient_mu    0.139
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89485
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.34 (release 07-07-2010 CrysAlis171 .NET)
(compiled Jul  7 2010,16:04:54)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.488
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             474
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.499
_refine_diff_density_min         -0.276
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     320
_refine_ls_number_reflns         5138
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0773
_refine_ls_R_factor_gt           0.0541
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0590P)²+0.5435P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1299
_refine_ls_wR_factor_ref         0.1484
_reflns_number_gt                3761
_reflns_number_total             5138
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3ob41762j.txt
_cod_data_source_block           x1n1_angelo_120k
_cod_database_code               7153199
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
C1 C 0.1692(2) 0.73587(15) 0.13700(15) 0.0276(3) Uani 1 1 d .
C2 C 0.0128(2) 0.66117(15) 0.11005(15) 0.0275(3) Uani 1 1 d .
C3 C -0.0074(2) 0.56301(15) 0.17252(16) 0.0299(4) Uani 1 1 d .
C4 C 0.2690(2) 0.60584(16) 0.27581(15) 0.0313(4) Uani 1 1 d .
C5 C 0.2986(2) 0.70305(16) 0.21689(16) 0.0301(4) Uani 1 1 d .
C6 C 0.3961(3) 0.56923(19) 0.36686(18) 0.0427(5) Uani 1 1 d .
H6A H 0.3761 0.4815 0.3661 0.051 Uiso 1 1 d R
H6B H 0.3699 0.5946 0.4431 0.051 Uiso 1 1 d R
C7A C 0.5578(4) 0.6093(4) 0.3549(3) 0.0483(9) Uani 0.718(6) 1 d P
C7B C 0.5581(9) 0.6715(9) 0.4082(8) 0.0483(9) Uani 0.282(6) 1 d P
H7A H 0.6283 0.6045 0.4300 0.058 Uiso 1 1 d R
H7B H 0.5750 0.5651 0.2765 0.058 Uiso 1 1 d R
C8A C 0.5787(5) 0.7490(5) 0.3534(5) 0.0551(13) Uani 0.654(9) 1 d P
C8B C 0.5984(10) 0.7167(9) 0.3003(9) 0.0551(13) Uani 0.346(9) 1 d P
H8A H 0.6848 0.7679 0.3394 0.066 Uiso 1 1 d R
H8B H 0.5499 0.7956 0.4316 0.066 Uiso 1 1 d R
C9 C 0.4660(2) 0.77195(19) 0.23856(19) 0.0422(5) Uani 1 1 d .
H9A H 0.4991 0.7623 0.1631 0.051 Uiso 1 1 d R
H9B H 0.4656 0.8566 0.2554 0.051 Uiso 1 1 d R
C10 C -0.1562(2) 0.48226(17) 0.14825(19) 0.0390(4) Uani 1 1 d .
H10 H -0.1688 0.4195 0.1919 0.047 Uiso 1 1 calc R
C11 C -0.2817(2) 0.49787(19) 0.0594(2) 0.0453(5) Uani 1 1 d .
H11 H -0.3804 0.4460 0.0436 0.054 Uiso 1 1 calc R
C12 C -0.2631(2) 0.59021(17) -0.00723(18) 0.0359(4) Uani 1 1 d .
H12 H -0.3482 0.5969 -0.0695 0.043 Uiso 1 1 calc R
C13 C -0.1206(2) 0.67190(16) 0.01759(17) 0.0318(4) Uani 1 1 d .
H13 H -0.1113 0.7347 -0.0264 0.038 Uiso 1 1 calc R
C14 C 0.0955(2) 0.91587(16) 0.04074(16) 0.0307(4) Uani 1 1 d .
C15 C 0.0039(2) 0.97133(17) 0.11219(17) 0.0335(4) Uani 1 1 d .
H15 H 0.0070 0.9523 0.1876 0.040 Uiso 1 1 calc R
C16 C 0.0926(2) 0.94489(17) -0.07132(17) 0.0329(4) Uani 1 1 d .
H16 H 0.1551 0.9082 -0.1188 0.039 Uiso 1 1 calc R
C17 C 0.4559(3) 0.19116(19) 0.2583(2) 0.0490(5) Uani 1 1 d .
C18 C 0.5056(2) 0.14900(17) 0.14124(18) 0.0355(4) Uani 1 1 d .
C19 C -0.0588(3) 0.1740(2) 0.4478(2) 0.0499(5) Uani 1 1 d .
C20 C -0.0130(3) 0.31017(18) 0.43221(17) 0.0394(4) Uani 1 1 d .
N1 N 0.19998(18) 0.83329(15) 0.08332(15) 0.0370(4) Uani 1 1 d .
H1 H 0.2972 0.8611 0.0900 0.044 Uiso 1 1 d R
N2 N 0.12084(18) 0.54122(13) 0.25398(13) 0.0307(3) Uani 1 1 d .
H2 H 0.1012 0.4780 0.2912 0.037 Uiso 1 1 d R
O1 O 0.47544(16) 0.02949(11) 0.10016(12) 0.0372(3) Uani 1 1 d .
O2 O 0.5644(2) 0.22960(14) 0.09779(17) 0.0606(5) Uani 1 1 d .
O3A O -0.0793(6) 0.3960(4) 0.4934(4) 0.0535(9) Uani 0.521(5) 1 d P
O3B O 0.0087(7) 0.3860(4) 0.5282(4) 0.0535(9) Uani 0.479(5) 1 d P
O4 O 0.0393(3) 0.32436(15) 0.34854(17) 0.0694(6) Uani 1 1 d .
F1 F 0.5626(2) 0.28607(14) 0.33337(14) 0.0803(5) Uani 1 1 d .
F2 F 0.31777(19) 0.23499(16) 0.23350(15) 0.0743(5) Uani 1 1 d .
F3 F 0.4365(3) 0.10071(14) 0.31779(14) 0.0822(6) Uani 1 1 d .
F4A F -0.1718(2) 0.10576(19) 0.3510(3) 0.0672(7) Uani 0.858(6) 1 d P
F4B F -0.1967(17) 0.1338(12) 0.4127(17) 0.0672(7) Uani 0.142(6) 1 d P
F5A F 0.0623(3) 0.1093(2) 0.4410(4) 0.0741(9) Uani 0.855(9) 1 d P
F5B F 0.043(2) 0.1326(14) 0.504(2) 0.0741(9) Uani 0.145(9) 1 d P
F6A F -0.114(2) 0.1621(7) 0.5426(8) 0.065(3) Uani 0.455(4) 1 d P
F6B F -0.0371(18) 0.1770(8) 0.5671(9) 0.065(3) Uani 0.322(10) 1 d P
F6C F -0.1769(19) 0.1754(13) 0.5171(12) 0.065(3) Uani 0.223(10) 1 d P
H1A H 0.5000 0.0000 0.0000 0.098(14) Uiso 1 2 d S
H3A H 0.0000 0.5000 0.5000 0.15(2) Uiso 1 2 d S
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.003 0.002 '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'
F F 0.017 0.01 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.006 0.003 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.011 0.006 '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
C20 O3A H3A 106.00 . . no
C20 O3B H3A 106.00 . . no
C18 O1 H1A 112.00 . . no
C1 N1 C14 128.45(16) . . yes
C3 N2 C4 123.41(15) . . yes
C14 N1 H1 113.00 . . no
C1 N1 H1 117.00 . . no
C4 N2 H2 121.00 . . no
C3 N2 H2 116.00 . . no
N1 C1 C5 118.05(16) . . yes
C2 C1 C5 119.56(15) . . no
N1 C1 C2 122.30(16) . . yes
C3 C2 C13 117.22(16) . . no
C1 C2 C3 117.87(15) . . no
C1 C2 C13 124.70(15) . . no
C2 C3 C10 121.42(17) . . no
N2 C3 C10 119.04(16) . . yes
N2 C3 C2 119.47(16) . . yes
C5 C4 C6 122.95(17) . . no
N2 C4 C6 116.61(16) . . yes
N2 C4 C5 120.43(16) . . yes
C1 C5 C4 119.03(16) . . no
C4 C5 C9 120.09(16) . . no
C1 C5 C9 120.89(16) . . no
C4 C6 C7A 112.9(2) . . no
C4 C6 C7B 112.2(4) . . no
C5 C9 C8A 111.9(2) . . no
C5 C9 C8B 118.4(4) . . no
C3 C10 C11 118.99(18) . . no
C10 C11 C12 120.8(2) . . no
C11 C12 C13 120.95(19) . . no
C2 C13 C12 120.56(17) . . no
N1 C14 C15 120.68(17) . . yes
C15 C14 C16 120.31(17) . . no
N1 C14 C16 118.93(16) . . yes
C14 C15 C16 119.97(17) . 2_575 no
C14 C16 C15 119.71(17) . 2_575 no
C4 C6 H6B 105.00 . . no
H6A C6 H6B 94.00 . . no
C7B C6 H6A 132.00 . . no
C4 C6 H6A 112.00 . . no
C7A C6 H6A 112.00 . . no
C7A C6 H6B 120.00 . . no
C7B C6 H6B 92.00 . . no
H7A C7A H7B 120.00 . . no
C6 C7A H7B 112.00 . . no
C6 C7A H7A 105.00 . . no
H7A C7B H8B 144.00 . . no
C6 C7B H7A 93.00 . . no
C6 C7B H8B 120.00 . . no
C9 C8A H8A 103.00 . . no
H8A C8A H8B 121.00 . . no
C9 C8A H8B 110.00 . . no
C9 C8B H8A 117.00 . . no
C8A C9 H9A 120.00 . . no
C5 C9 H9A 110.00 . . no
C8A C9 H9B 104.00 . . no
C5 C9 H9B 109.00 . . no
C8B C9 H9B 121.00 . . no
C8B C9 H9A 94.00 . . no
H9A C9 H9B 101.00 . . no
C11 C10 H10 120.00 . . no
C3 C10 H10 121.00 . . no
C12 C11 H11 120.00 . . no
C10 C11 H11 120.00 . . no
C11 C12 H12 120.00 . . no
C13 C12 H12 120.00 . . no
C2 C13 H13 120.00 . . no
C12 C13 H13 120.00 . . no
C14 C15 H15 120.00 . . no
C16 C15 H15 120.00 2_575 . no
C15 C16 H16 120.00 2_575 . no
C14 C16 H16 120.00 . . no
F4A C19 C20 110.9(2) . . yes
F6A C19 C20 116.7(4) . . yes
F4B C19 C20 114.1(7) . . yes
F5B C19 C20 115.8(9) . . yes
F6C C19 C20 108.1(6) . . yes
F5A C19 C20 109.9(2) . . yes
F6B C19 C20 108.4(5) . . yes
O3A C20 O4 124.7(3) . . yes
O3B C20 C19 110.4(3) . . yes
O4 C20 C19 118.54(19) . . yes
O3B C20 O4 127.1(3) . . yes
O3A C20 C19 113.8(3) . . yes
F1 C17 F2 106.63(19) . . yes
F1 C17 F3 107.55(19) . . yes
F2 C17 F3 107.5(2) . . yes
F2 C17 C18 109.63(18) . . yes
F3 C17 C18 114.29(19) . . yes
F1 C17 C18 111.0(2) . . yes
O1 C18 C17 113.79(17) . . yes
O2 C18 C17 118.24(18) . . yes
O1 C18 O2 127.96(19) . . yes
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
F4A C19 1.340(4) . yes
F4B C19 1.176(17) . yes
F5A C19 1.344(4) . yes
F5B C19 1.161(19) . yes
F6A C19 1.315(12) . yes
F6B C19 1.344(10) . yes
F6C C19 1.439(16) . yes
F1 C17 1.327(3) . yes
F2 C17 1.336(3) . yes
F3 C17 1.315(3) . yes
O3A C20 1.333(6) . yes
O3B C20 1.218(5) . yes
O4 C20 1.187(3) . yes
O3A H3A 1.2300 . no
O3B H3A 1.3400 . no
O1 C18 1.271(2) . yes
O2 C18 1.206(3) . yes
O1 H1A 1.2200 . no
N1 C1 1.352(2) . yes
N1 C14 1.424(2) . yes
N2 C3 1.364(2) . yes
N2 C4 1.339(2) . yes
N1 H1 0.8500 . no
N2 H2 0.8900 . no
C1 C5 1.413(2) . no
C1 C2 1.436(2) . no
C2 C13 1.423(3) . no
C2 C3 1.410(2) . no
C3 C10 1.415(3) . no
C4 C5 1.388(2) . no
C4 C6 1.492(3) . no
C5 C9 1.501(3) . no
C6 C7B 1.612(9) . no
C6 C7A 1.468(5) . no
C8A C9 1.546(6) . no
C8B C9 1.463(10) . no
C10 C11 1.372(3) . no
C11 C12 1.390(3) . no
C12 C13 1.376(3) . no
C14 C16 1.387(3) . no
C14 C15 1.383(3) . no
C15 C16 1.384(3) 2_575 no
C6 H6A 0.9500 . no
C6 H6B 0.9600 . no
C7A H7A 0.9600 . no
C7A H7B 0.9900 . no
C7B H8B 1.3400 . no
C7B H7A 1.0300 . no
C8A H8A 0.9800 . no
C8A H8B 1.0600 . no
C8B H8A 0.8600 . no
C9 H9A 0.9700 . no
C9 H9B 0.9000 . no
C10 H10 0.9300 . no
C11 H11 0.9300 . no
C12 H12 0.9300 . no
C13 H13 0.9300 . no
C15 H15 0.9300 . no
C16 H16 0.9300 . no
C19 C20 1.540(3) . no
C17 C18 1.524(3) . 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
N1 H1 O1 0.8500 2.2200 2.958(2) 146.00 1_565 yes
O1 H1A O1 1.2200 1.2200 2.4392(19) 180.00 2_655 yes
N2 H2 O4 0.8900 1.9700 2.856(2) 171.00 1_555 yes
O3A H3A O3A 1.2300 1.2300 2.464(7) 180.00 2_566 yes
C11 H11 O2 0.9300 2.5600 3.209(3) 127.00 1_455 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
C14 N1 C1 C2 30.7(3) . . no
C14 N1 C1 C5 -152.99(18) . . no
C1 N1 C14 C15 47.0(3) . . no
C1 N1 C14 C16 -136.1(2) . . no
C4 N2 C3 C10 174.52(17) . . no
C3 N2 C4 C5 1.7(3) . . no
C3 N2 C4 C6 -179.42(17) . . no
C4 N2 C3 C2 -2.4(3) . . no
C5 C1 C2 C3 4.8(2) . . no
C2 C1 C5 C4 -5.5(3) . . no
N1 C1 C5 C9 -1.8(3) . . no
N1 C1 C2 C3 -178.94(16) . . no
N1 C1 C2 C13 6.5(3) . . no
C5 C1 C2 C13 -169.70(17) . . no
N1 C1 C5 C4 178.09(16) . . no
C2 C1 C5 C9 174.65(16) . . no
C3 C2 C13 C12 0.9(3) . . no
C1 C2 C3 N2 -1.0(2) . . no
C1 C2 C3 C10 -177.78(17) . . no
C13 C2 C3 N2 173.96(16) . . no
C13 C2 C3 C10 -2.8(3) . . no
C1 C2 C13 C12 175.49(17) . . no
N2 C3 C10 C11 -174.85(18) . . no
C2 C3 C10 C11 2.0(3) . . no
N2 C4 C5 C1 2.3(3) . . no
C6 C4 C5 C9 3.4(3) . . no
N2 C4 C5 C9 -177.85(17) . . no
C6 C4 C5 C1 -176.49(17) . . no
C5 C4 C6 C7A -21.5(3) . . no
N2 C4 C6 C7A 159.7(2) . . no
C4 C5 C9 C8A -16.3(3) . . no
C1 C5 C9 C8A 163.5(3) . . no
C3 C10 C11 C12 0.9(3) . . no
C10 C11 C12 C13 -2.8(3) . . no
C11 C12 C13 C2 1.9(3) . . no
N1 C14 C15 C16 177.58(17) . 2_575 no
C16 C14 C15 C16 0.7(3) . 2_575 no
N1 C14 C16 C15 -177.63(17) . 2_575 no
C15 C14 C16 C15 -0.7(3) . 2_575 no
C14 C15 C16 C14 -0.7(3) 2_575 2_575 no
F4A C19 C20 O3A 101.5(3) . . no
F4A C19 C20 O4 -59.8(3) . . no
F5A C19 C20 O3A -148.5(4) . . no
F5A C19 C20 O4 50.2(4) . . no
F1 C17 C18 O1 141.55(18) . . no
F1 C17 C18 O2 -39.8(3) . . no
F2 C17 C18 O1 -101.0(2) . . no
F2 C17 C18 O2 77.8(2) . . no
F3 C17 C18 O1 19.7(3) . . no
F3 C17 C18 O2 -161.6(2) . . no
