#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/48/1514864.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_1514864
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            'C16 H14 N2 O2 S'
_chemical_formula_weight         298.35
_chemical_name_systematic
;
?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 106.839(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.7184(4)
_cell_length_b                   13.6885(6)
_cell_length_c                   10.8658(5)
_cell_measurement_reflns_used    9957
_cell_measurement_temperature    90.0(1)
_cell_measurement_theta_max      30.1
_cell_measurement_theta_min      2.46
_cell_volume                     1383.50(11)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      90.0(1)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0384
_diffrn_reflns_av_sigmaI/netI    0.0278
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            21989
_diffrn_reflns_theta_full        30.10
_diffrn_reflns_theta_max         30.10
_diffrn_reflns_theta_min         2.19
_exptl_absorpt_coefficient_mu    0.240
_exptl_absorpt_correction_T_max  0.965
_exptl_absorpt_correction_T_min  0.813
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, Sheldrick (2008)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.432
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.392
_refine_diff_density_min         -0.437
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         4066
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0536
_refine_ls_R_factor_gt           0.0371
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0344P)²+1.1247P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0847
_refine_ls_wR_factor_ref         0.0950
_reflns_number_gt                3256
_reflns_number_total             4066
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            c3mb25600f.txt
_cod_data_source_block           co410
_cod_original_cell_volume        1383.50(10)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1514864
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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 0.69948(14) 0.94302(9) 0.98859(13) 0.0141(2) Uani 1 1 d .
C2 C 0.60684(14) 0.89799(9) 1.04821(13) 0.0140(2) Uani 1 1 d .
C3 C 0.62031(16) 0.92370(10) 1.17608(14) 0.0170(3) Uani 1 1 d .
H3 H 0.5588 0.8942 1.2193 0.020 Uiso 1 1 calc R
C4 C 0.72162(16) 0.99129(10) 1.24039(14) 0.0190(3) Uani 1 1 d .
H4 H 0.7293 1.0079 1.3270 0.023 Uiso 1 1 calc R
C5 C 0.81195(15) 1.03478(10) 1.17823(14) 0.0185(3) Uani 1 1 d .
H5 H 0.8812 1.0814 1.2224 0.022 Uiso 1 1 calc R
C6 C 0.80158(15) 1.01060(10) 1.05236(14) 0.0166(3) Uani 1 1 d .
H6 H 0.8638 1.0400 1.0099 0.020 Uiso 1 1 calc R
C7 C 0.78712(15) 0.87895(10) 0.82290(14) 0.0172(3) Uani 1 1 d .
C8 C 0.62686(17) 0.91623(12) 0.60572(14) 0.0230(3) Uani 1 1 d .
H8A H 0.5522 0.9264 0.6487 0.035 Uiso 1 1 calc R
H8B H 0.5891 0.8746 0.5300 0.035 Uiso 1 1 calc R
H8C H 0.6559 0.9794 0.5789 0.035 Uiso 1 1 calc R
C9 C 0.85139(19) 0.82122(13) 0.63771(17) 0.0284(4) Uani 1 1 d .
H9A H 0.8990 0.8703 0.5986 0.043 Uiso 1 1 calc R
H9B H 0.7994 0.7750 0.5716 0.043 Uiso 1 1 calc R
H9C H 0.9237 0.7860 0.7048 0.043 Uiso 1 1 calc R
C12 C 0.49465(14) 0.82741(9) 0.98458(13) 0.0129(2) Uani 1 1 d .
C14 C 0.32970(14) 0.71293(9) 0.84252(13) 0.0131(2) Uani 1 1 d .
C15 C 0.30733(14) 0.72968(9) 0.96266(13) 0.0135(2) Uani 1 1 d .
C16 C 0.19233(16) 0.68422(10) 0.99301(14) 0.0178(3) Uani 1 1 d .
H16 H 0.1765 0.6944 1.0743 0.021 Uiso 1 1 calc R
C17 C 0.10243(16) 0.62438(10) 0.90266(14) 0.0187(3) Uani 1 1 d .
H17 H 0.0231 0.5940 0.9216 0.022 Uiso 1 1 calc R
C18 C 0.12630(16) 0.60774(10) 0.78339(14) 0.0178(3) Uani 1 1 d .
H18 H 0.0629 0.5661 0.7228 0.021 Uiso 1 1 calc R
C19 C 0.24037(15) 0.65073(10) 0.75232(13) 0.0160(3) Uani 1 1 d .
H19 H 0.2575 0.6383 0.6720 0.019 Uiso 1 1 calc R
N1 N 0.75076(14) 0.86911(9) 0.69418(12) 0.0203(3) Uani 1 1 d .
N11 N 0.40340(13) 0.79402(8) 1.04163(11) 0.0140(2) Uani 1 1 d .
O1 O 0.67812(10) 0.92568(7) 0.85821(9) 0.0156(2) Uani 1 1 d .
O2 O 0.89574(12) 0.85061(8) 0.90006(11) 0.0237(2) Uani 1 1 d .
S13 S 0.47378(4) 0.78209(2) 0.82945(3) 0.01402(9) 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'
S S 0.1246 0.1234 '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
C6 C1 O1 119.79(12)
C6 C1 C2 121.82(13)
O1 C1 C2 118.11(12)
C1 C2 C3 117.48(12)
C1 C2 C12 124.19(12)
C3 C2 C12 118.32(12)
C4 C3 C2 121.11(13)
C4 C3 H3 119.4
C2 C3 H3 119.4
C3 C4 C5 119.94(14)
C3 C4 H4 120.0
C5 C4 H4 120.0
C6 C5 C4 120.26(13)
C6 C5 H5 119.9
C4 C5 H5 119.9
C5 C6 C1 119.39(13)
C5 C6 H6 120.3
C1 C6 H6 120.3
O2 C7 N1 127.11(14)
O2 C7 O1 122.83(13)
N1 C7 O1 110.04(12)
N1 C8 H8A 109.5
N1 C8 H8B 109.5
H8A C8 H8B 109.5
N1 C8 H8C 109.5
H8A C8 H8C 109.5
H8B C8 H8C 109.5
N1 C9 H9A 109.5
N1 C9 H9B 109.5
H9A C9 H9B 109.5
N1 C9 H9C 109.5
H9A C9 H9C 109.5
H9B C9 H9C 109.5
N11 C12 C2 121.38(12)
N11 C12 S13 115.37(10)
C2 C12 S13 123.25(10)
C19 C14 C15 121.39(12)
C19 C14 S13 129.06(11)
C15 C14 S13 109.53(10)
N11 C15 C16 125.28(12)
N11 C15 C14 114.95(12)
C16 C15 C14 119.75(12)
C17 C16 C15 118.75(13)
C17 C16 H16 120.6
C15 C16 H16 120.6
C16 C17 C18 121.00(13)
C16 C17 H17 119.5
C18 C17 H17 119.5
C19 C18 C17 121.14(13)
C19 C18 H18 119.4
C17 C18 H18 119.4
C18 C19 C14 117.95(13)
C18 C19 H19 121.0
C14 C19 H19 121.0
C7 N1 C9 118.53(14)
C7 N1 C8 124.02(13)
C9 N1 C8 116.77(13)
C12 N11 C15 110.96(11)
C7 O1 C1 117.44(11)
C14 S13 C12 89.18(6)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C6 1.3864(19)
C1 O1 1.3915(16)
C1 C2 1.3957(19)
C2 C3 1.4022(19)
C2 C12 1.4709(18)
C3 C4 1.384(2)
C3 H3 0.9500
C4 C5 1.387(2)
C4 H4 0.9500
C5 C6 1.382(2)
C5 H5 0.9500
C6 H6 0.9500
C7 O2 1.2062(18)
C7 N1 1.3465(19)
C7 O1 1.3834(17)
C8 N1 1.456(2)
C8 H8A 0.9800
C8 H8B 0.9800
C8 H8C 0.9800
C9 N1 1.453(2)
C9 H9A 0.9800
C9 H9B 0.9800
C9 H9C 0.9800
C12 N11 1.3032(17)
C12 S13 1.7519(13)
C14 C19 1.3952(19)
C14 C15 1.4030(18)
C14 S13 1.7298(13)
C15 N11 1.3855(17)
C15 C16 1.3995(19)
C16 C17 1.379(2)
C16 H16 0.9500
C17 C18 1.400(2)
C17 H17 0.9500
C18 C19 1.3806(19)
C18 H18 0.9500
C19 H19 0.9500
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
C6 C1 C2 C3 0.1(2)
O1 C1 C2 C3 -173.75(12)
C6 C1 C2 C12 178.68(12)
O1 C1 C2 C12 4.82(19)
C1 C2 C3 C4 0.1(2)
C12 C2 C3 C4 -178.58(13)
C2 C3 C4 C5 0.0(2)
C3 C4 C5 C6 -0.3(2)
C4 C5 C6 C1 0.4(2)
O1 C1 C6 C5 173.39(12)
C2 C1 C6 C5 -0.4(2)
C1 C2 C12 N11 -174.10(13)
C3 C2 C12 N11 4.47(19)
C1 C2 C12 S13 6.13(19)
C3 C2 C12 S13 -175.31(10)
C19 C14 C15 N11 -179.26(12)
S13 C14 C15 N11 -1.02(15)
C19 C14 C15 C16 -0.7(2)
S13 C14 C15 C16 177.52(11)
N11 C15 C16 C17 177.75(13)
C14 C15 C16 C17 -0.6(2)
C15 C16 C17 C18 1.0(2)
C16 C17 C18 C19 -0.1(2)
C17 C18 C19 C14 -1.3(2)
C15 C14 C19 C18 1.6(2)
S13 C14 C19 C18 -176.22(11)
O2 C7 N1 C9 -1.3(2)
O1 C7 N1 C9 -179.76(12)
O2 C7 N1 C8 -171.55(14)
O1 C7 N1 C8 9.98(19)
C2 C12 N11 C15 179.31(11)
S13 C12 N11 C15 -0.90(15)
C16 C15 N11 C12 -177.21(13)
C14 C15 N11 C12 1.24(16)
O2 C7 O1 C1 2.38(19)
N1 C7 O1 C1 -179.07(11)
C6 C1 O1 C7 68.96(16)
C2 C1 O1 C7 -117.06(13)
C19 C14 S13 C12 178.48(13)
C15 C14 S13 C12 0.42(10)
N11 C12 S13 C14 0.28(11)
C2 C12 S13 C14 -179.93(11)
