#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/48/1514862.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_1514862
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            'C15 H16 N2 O3'
_chemical_formula_weight         272.30
_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                97.746(3)
_cell_angle_beta                 110.719(3)
_cell_angle_gamma                95.600(3)
_cell_formula_units_Z            2
_cell_length_a                   7.9251(4)
_cell_length_b                   8.3409(4)
_cell_length_c                   11.1686(6)
_cell_measurement_reflns_used    6462
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.26
_cell_measurement_theta_min      2.75
_cell_volume                     675.77(6)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Bruker X8 APEX II'
_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  0.0269
_diffrn_reflns_av_sigmaI/netI    0.0280
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            12110
_diffrn_reflns_theta_full        28.32
_diffrn_reflns_theta_max         28.32
_diffrn_reflns_theta_min         2.75
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  0.993
_exptl_absorpt_correction_T_min  0.903
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.338
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             288
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.369
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     184
_refine_ls_number_reflns         3322
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.0552
_refine_ls_R_factor_gt           0.0415
_refine_ls_shift/su_max          0.030
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0630P)²+0.2032P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1079
_refine_ls_wR_factor_ref         0.1176
_reflns_number_gt                2665
_reflns_number_total             3322
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            c3mb25600f.txt
_cod_data_source_block           co397
_cod_database_code               1514862
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 0.16144(18) 0.85429(16) 0.07540(12) 0.0214(3) Uani 1 1 d .
H1A H 0.0324 0.8592 0.0277 0.032 Uiso 1 1 calc R
H1B H 0.2378 0.9422 0.0594 0.032 Uiso 1 1 calc R
H1C H 0.1855 0.8678 0.1688 0.032 Uiso 1 1 calc R
C2 C 0.20533(16) 0.69137(15) 0.02986(11) 0.0172(3) Uani 1 1 d .
C3 C 0.23402(16) 0.57011(15) 0.10199(11) 0.0174(3) Uani 1 1 d .
C4 C 0.27212(16) 0.41065(16) 0.05951(12) 0.0181(3) Uani 1 1 d .
C5 C 0.28282(17) 0.39269(16) -0.06821(12) 0.0198(3) Uani 1 1 d .
H5 H 0.3085 0.2925 -0.1042 0.024 Uiso 1 1 calc R
C6 C 0.25705(17) 0.51560(16) -0.13748(12) 0.0192(3) Uani 1 1 d .
H6 H 0.2680 0.4997 -0.2201 0.023 Uiso 1 1 calc R
C7 C 0.19202(17) 0.78829(15) -0.17285(11) 0.0178(3) Uani 1 1 d .
C8 C 0.01724(18) 0.81770(17) -0.24180(12) 0.0216(3) Uani 1 1 d .
H8 H -0.0870 0.7569 -0.2367 0.026 Uiso 1 1 calc R
C9 C -0.00141(19) 0.93882(17) -0.31881(12) 0.0238(3) Uani 1 1 d .
H9 H -0.1196 0.9600 -0.3675 0.029 Uiso 1 1 calc R
C10 C 0.15231(19) 1.02856(16) -0.32452(12) 0.0226(3) Uani 1 1 d .
H10 H 0.1387 1.1118 -0.3760 0.027 Uiso 1 1 calc R
C11 C 0.32544(19) 0.99672(16) -0.25509(13) 0.0229(3) Uani 1 1 d .
H11 H 0.4299 1.0579 -0.2597 0.028 Uiso 1 1 calc R
C12 C 0.34682(18) 0.87539(16) -0.17862(12) 0.0209(3) Uani 1 1 d .
H12 H 0.4650 0.8527 -0.1314 0.025 Uiso 1 1 calc R
C13 C 0.38003(17) 0.64185(15) 0.32853(11) 0.0178(3) Uani 1 1 d .
C14 C 0.5115(2) 0.71737(19) 0.56266(12) 0.0275(3) Uani 1 1 d .
H14A H 0.6216 0.6915 0.5484 0.041 Uiso 1 1 calc R
H14B H 0.4958 0.6611 0.6305 0.041 Uiso 1 1 calc R
H14C H 0.5236 0.8359 0.5902 0.041 Uiso 1 1 calc R
C15 C 0.1744(2) 0.6315(2) 0.45207(14) 0.0299(3) Uani 1 1 d .
H15A H 0.0780 0.6267 0.3668 0.045 Uiso 1 1 calc R
H15B H 0.1636 0.7198 0.5151 0.045 Uiso 1 1 calc R
H15C H 0.1619 0.5268 0.4812 0.045 Uiso 1 1 calc R
N1 N 0.21566(14) 0.66233(13) -0.09260(10) 0.0175(2) Uani 1 1 d .
N2 N 0.35245(15) 0.66296(14) 0.44172(10) 0.0225(3) Uani 1 1 d .
O1 O 0.29409(13) 0.30097(11) 0.12748(9) 0.0232(2) Uani 1 1 d .
O2 O 0.21648(12) 0.59698(11) 0.22358(8) 0.0199(2) Uani 1 1 d .
O3 O 0.52718(12) 0.66193(12) 0.31685(9) 0.0231(2) Uani 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 118.31(11)
C3 C2 C1 123.42(11)
N1 C2 C1 118.26(11)
C2 C3 O2 118.33(11)
C2 C3 C4 124.68(11)
O2 C3 C4 116.91(10)
O1 C4 C5 124.11(11)
O1 C4 C3 122.89(11)
C5 C4 C3 113.00(11)
C6 C5 C4 121.45(11)
C6 C5 H5 119.3
C4 C5 H5 119.3
C5 C6 N1 122.37(11)
C5 C6 H6 118.8
N1 C6 H6 118.8
C12 C7 C8 121.93(12)
C12 C7 N1 118.36(11)
C8 C7 N1 119.70(11)
C7 C8 C9 118.45(12)
C7 C8 H8 120.8
C9 C8 H8 120.8
C10 C9 C8 120.37(12)
C10 C9 H9 119.8
C8 C9 H9 119.8
C11 C10 C9 120.15(12)
C11 C10 H10 119.9
C9 C10 H10 119.9
C10 C11 C12 120.34(12)
C10 C11 H11 119.8
C12 C11 H11 119.8
C7 C12 C11 118.75(12)
C7 C12 H12 120.6
C11 C12 H12 120.6
O3 C13 N2 125.96(11)
O3 C13 O2 122.96(11)
N2 C13 O2 111.06(10)
N2 C14 H14A 109.5
N2 C14 H14B 109.5
H14A C14 H14B 109.5
N2 C14 H14C 109.5
H14A C14 H14C 109.5
H14B C14 H14C 109.5
N2 C15 H15A 109.5
N2 C15 H15B 109.5
H15A C15 H15B 109.5
N2 C15 H15C 109.5
H15A C15 H15C 109.5
H15B C15 H15C 109.5
C6 N1 C2 120.13(10)
C6 N1 C7 118.72(10)
C2 N1 C7 121.08(10)
C13 N2 C15 124.33(11)
C13 N2 C14 118.18(11)
C15 N2 C14 117.47(11)
C13 O2 C3 114.48(9)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.5025(17)
C1 H1A 0.9800
C1 H1B 0.9800
C1 H1C 0.9800
C2 C3 1.3633(17)
C2 N1 1.3891(15)
C3 O2 1.4040(13)
C3 C4 1.4474(18)
C4 O1 1.2523(15)
C4 C5 1.4474(17)
C5 C6 1.3543(17)
C5 H5 0.9500
C6 N1 1.3734(16)
C6 H6 0.9500
C7 C12 1.3898(18)
C7 C8 1.3908(18)
C7 N1 1.4545(15)
C8 C9 1.3984(18)
C8 H8 0.9500
C9 C10 1.3922(19)
C9 H9 0.9500
C10 C11 1.389(2)
C10 H10 0.9500
C11 C12 1.3951(18)
C11 H11 0.9500
C12 H12 0.9500
C13 O3 1.2167(15)
C13 N2 1.3491(15)
C13 O2 1.3806(15)
C14 N2 1.4620(17)
C14 H14A 0.9800
C14 H14B 0.9800
C14 H14C 0.9800
C15 N2 1.4575(17)
C15 H15A 0.9800
C15 H15B 0.9800
C15 H15C 0.9800
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 -177.52(10)
C1 C2 C3 O2 1.90(18)
N1 C2 C3 C4 -1.00(18)
C1 C2 C3 C4 178.43(12)
C2 C3 C4 O1 -178.50(12)
O2 C3 C4 O1 -1.93(17)
C2 C3 C4 C5 1.82(17)
O2 C3 C4 C5 178.38(10)
O1 C4 C5 C6 179.73(12)
C3 C4 C5 C6 -0.59(17)
C4 C5 C6 N1 -1.42(19)
C12 C7 C8 C9 -0.02(19)
N1 C7 C8 C9 -179.60(11)
C7 C8 C9 C10 -0.74(19)
C8 C9 C10 C11 0.92(19)
C9 C10 C11 C12 -0.35(19)
C8 C7 C12 C11 0.58(19)
N1 C7 C12 C11 -179.84(11)
C10 C11 C12 C7 -0.39(19)
C5 C6 N1 C2 2.36(18)
C5 C6 N1 C7 179.39(11)
C3 C2 N1 C6 -1.13(17)
C1 C2 N1 C6 179.41(11)
C3 C2 N1 C7 -178.09(11)
C1 C2 N1 C7 2.45(17)
C12 C7 N1 C6 -75.52(15)
C8 C7 N1 C6 104.07(14)
C12 C7 N1 C2 101.48(14)
C8 C7 N1 C2 -78.93(15)
O3 C13 N2 C15 -177.50(13)
O2 C13 N2 C15 3.93(18)
O3 C13 N2 C14 1.0(2)
O2 C13 N2 C14 -177.54(11)
O3 C13 O2 C3 2.34(17)
N2 C13 O2 C3 -179.04(10)
C2 C3 O2 C13 -100.14(13)
C4 C3 O2 C13 83.07(13)
