#------------------------------------------------------------------------------
#$Date: 2016-02-18 16:37:37 +0100 (jue 18 de feb de 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/48/1514865.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_1514865
loop_
_publ_author_name
'Telpoukhovskaia, Maria A.'
'Patrick, Brian O.'
'Rodríguez-Rodríguez, Cristina'
'Orvig, Chris'
_publ_section_title
;
 Exploring the multifunctionality of thioflavin- and deferiprone-based
 molecules as acetylcholinesterase inhibitors for potential application in
 Alzheimer's disease.
;
_journal_issue                   4
_journal_name_full               'Molecular bioSystems'
_journal_page_first              792
_journal_page_last               805
_journal_paper_doi               10.1039/c3mb25600f
_journal_volume                  9
_journal_year                    2013
_chemical_formula_sum            'C13 H15 N O3'
_chemical_formula_weight         233.26
_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_creation_method           SHELXL-97
_cell_angle_alpha                100.928(4)
_cell_angle_beta                 111.838(3)
_cell_angle_gamma                107.261(3)
_cell_formula_units_Z            2
_cell_length_a                   7.5969(11)
_cell_length_b                   9.6007(14)
_cell_length_c                   9.9994(15)
_cell_measurement_reflns_used    5812
_cell_measurement_temperature    90.0(1)
_cell_measurement_theta_max      28.73
_cell_measurement_theta_min      2.33
_cell_volume                     608.35(16)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      90.0(1)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEX DUO'
_diffrn_measurement_method       'area detector'
_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  0.0389
_diffrn_reflns_av_sigmaI/netI    0.0365
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            13793
_diffrn_reflns_theta_full        28.78
_diffrn_reflns_theta_max         28.78
_diffrn_reflns_theta_min         2.33
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  0.998
_exptl_absorpt_correction_T_min  0.788
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, Sheldrick (2008)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.273
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             248
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.379
_refine_diff_density_min         -0.307
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         3135
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0749
_refine_ls_R_factor_gt           0.0502
_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)+(0.0749P)²+0.2121P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1314
_refine_ls_wR_factor_ref         0.1473
_reflns_number_gt                2250
_reflns_number_total             3135
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            c3mb25600f.txt
_cod_data_source_block           co412
_cod_original_cell_volume        608.35(15)
_cod_database_code               1514865
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 0.1244(2) 0.0503(2) 0.79775(19) 0.0275(4) Uani 1 1 d .
H1A H 0.0598 0.1248 0.7970 0.041 Uiso 1 1 calc R
H1B H 0.1220 0.0063 0.8781 0.041 Uiso 1 1 calc R
H1C H 0.0476 -0.0329 0.6981 0.041 Uiso 1 1 calc R
C2 C 0.3444(2) 0.13108(17) 0.82830(16) 0.0173(3) Uani 1 1 d .
C3 C 0.4081(2) 0.10473(17) 0.71827(16) 0.0176(3) Uani 1 1 d .
C4 C 0.6206(2) 0.17497(17) 0.74907(17) 0.0180(3) Uani 1 1 d .
C5 C 0.7610(2) 0.27107(19) 0.90210(18) 0.0231(3) Uani 1 1 d .
H5 H 0.9046 0.3180 0.9306 0.028 Uiso 1 1 calc R
C6 C 0.6944(2) 0.29752(18) 1.00917(17) 0.0212(3) Uani 1 1 d .
H6 H 0.7920 0.3643 1.1107 0.025 Uiso 1 1 calc R
C7 C 0.4333(2) 0.26793(17) 1.09450(17) 0.0182(3) Uani 1 1 d .
C8 C 0.4934(3) 0.2118(2) 1.21433(19) 0.0280(4) Uani 1 1 d .
H8 H 0.5682 0.1480 1.2158 0.034 Uiso 1 1 calc R
C9 C 0.4431(3) 0.2501(2) 1.3322(2) 0.0340(4) Uani 1 1 d .
H9 H 0.4832 0.2125 1.4151 0.041 Uiso 1 1 calc R
C10 C 0.3346(3) 0.3429(2) 1.32867(19) 0.0304(4) Uani 1 1 d .
H10 H 0.2983 0.3675 1.4087 0.036 Uiso 1 1 calc R
C11 C 0.2781(2) 0.4007(2) 1.20967(19) 0.0270(4) Uani 1 1 d .
H11 H 0.2056 0.4662 1.2093 0.032 Uiso 1 1 calc R
C12 C 0.3274(2) 0.36284(19) 1.09057(17) 0.0221(3) Uani 1 1 d .
H12 H 0.2890 0.4016 1.0083 0.027 Uiso 1 1 calc R
C13 C 1.1034(3) 0.3599(2) 0.5984(2) 0.0290(4) Uani 1 1 d .
H13A H 1.2374 0.4443 0.6314 0.043 Uiso 1 1 calc R
H13B H 1.0018 0.3573 0.5013 0.043 Uiso 1 1 calc R
H13C H 1.1185 0.2610 0.5844 0.043 Uiso 1 1 calc R
N1 N 0.49078(18) 0.23030(14) 0.97405(14) 0.0171(3) Uani 1 1 d .
O1 O 0.67255(16) 0.14855(13) 0.64304(12) 0.0235(3) Uani 1 1 d .
O2 O 0.26579(16) 0.00795(14) 0.57502(12) 0.0251(3) Uani 1 1 d .
O3 O 1.0347(2) 0.38459(16) 0.71149(15) 0.0363(3) Uani 1 1 d .
H2O H 0.331(3) -0.016(3) 0.516(3) 0.037(6) Uiso 1 1 d .
H3O H 0.917(4) 0.298(3) 0.685(3) 0.054(7) 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 0.0033 0.0016 '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 0.0061 0.0033 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C2 C1 H1A 109.5
C2 C1 H1B 109.5
H1A C1 H1B 109.5
C2 C1 H1C 109.5
H1A C1 H1C 109.5
H1B C1 H1C 109.5
C3 C2 N1 118.40(13)
C3 C2 C1 122.29(13)
N1 C2 C1 119.24(13)
O2 C3 C2 118.83(13)
O2 C3 C4 118.61(13)
C2 C3 C4 122.55(13)
O1 C4 C5 124.19(13)
O1 C4 C3 120.44(13)
C5 C4 C3 115.37(13)
C6 C5 C4 121.20(13)
C6 C5 H5 119.4
C4 C5 H5 119.4
C5 C6 N1 121.33(14)
C5 C6 H6 119.3
N1 C6 H6 119.3
C12 C7 C8 121.67(14)
C12 C7 N1 119.61(13)
C8 C7 N1 118.68(13)
C7 C8 C9 119.12(16)
C7 C8 H8 120.4
C9 C8 H8 120.4
C10 C9 C8 119.87(16)
C10 C9 H9 120.1
C8 C9 H9 120.1
C9 C10 C11 120.65(15)
C9 C10 H10 119.7
C11 C10 H10 119.7
C10 C11 C12 120.00(16)
C10 C11 H11 120.0
C12 C11 H11 120.0
C7 C12 C11 118.67(15)
C7 C12 H12 120.7
C11 C12 H12 120.7
O3 C13 H13A 109.5
O3 C13 H13B 109.5
H13A C13 H13B 109.5
O3 C13 H13C 109.5
H13A C13 H13C 109.5
H13B C13 H13C 109.5
C6 N1 C2 121.11(12)
C6 N1 C7 117.52(12)
C2 N1 C7 121.36(12)
C3 O2 H2O 110.6(14)
C13 O3 H3O 108.4(16)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.500(2)
C1 H1A 0.9800
C1 H1B 0.9800
C1 H1C 0.9800
C2 C3 1.368(2)
C2 N1 1.3810(18)
C3 O2 1.3532(17)
C3 C4 1.4356(19)
C4 O1 1.2699(17)
C4 C5 1.413(2)
C5 C6 1.357(2)
C5 H5 0.9500
C6 N1 1.3604(18)
C6 H6 0.9500
C7 C12 1.380(2)
C7 C8 1.385(2)
C7 N1 1.4464(18)
C8 C9 1.387(2)
C8 H8 0.9500
C9 C10 1.378(3)
C9 H9 0.9500
C10 C11 1.385(3)
C10 H10 0.9500
C11 C12 1.393(2)
C11 H11 0.9500
C12 H12 0.9500
C13 O3 1.4211(19)
C13 H13A 0.9800
C13 H13B 0.9800
C13 H13C 0.9800
O2 H2O 0.94(2)
O3 H3O 0.92(3)
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
N1 C2 C3 O2 -179.85(13)
C1 C2 C3 O2 3.2(2)
N1 C2 C3 C4 0.6(2)
C1 C2 C3 C4 -176.40(15)
O2 C3 C4 O1 1.2(2)
C2 C3 C4 O1 -179.24(14)
O2 C3 C4 C5 -178.29(14)
C2 C3 C4 C5 1.3(2)
O1 C4 C5 C6 178.35(15)
C3 C4 C5 C6 -2.2(2)
C4 C5 C6 N1 1.3(3)
C12 C7 C8 C9 1.0(2)
N1 C7 C8 C9 178.57(15)
C7 C8 C9 C10 0.0(3)
C8 C9 C10 C11 -1.1(3)
C9 C10 C11 C12 1.2(2)
C8 C7 C12 C11 -0.9(2)
N1 C7 C12 C11 -178.43(13)
C10 C11 C12 C7 -0.2(2)
C5 C6 N1 C2 0.8(2)
C5 C6 N1 C7 -178.61(14)
C3 C2 N1 C6 -1.7(2)
C1 C2 N1 C6 175.42(14)
C3 C2 N1 C7 177.68(13)
C1 C2 N1 C7 -5.2(2)
C12 C7 N1 C6 107.45(16)
C8 C7 N1 C6 -70.15(19)
C12 C7 N1 C2 -71.92(19)
C8 C7 N1 C2 110.48(16)
