#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/37/1513741.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_1513741
loop_
_publ_author_name
'Telpoukhovskaia, Maria A.'
'Rodríguez-Rodríguez, Cristina'
'Cawthray, Jacqueline F.'
'Scott, Lauren E.'
'Page, Brent D. G.'
'Alí-Torres, Jorge'
'Sodupe, Mariona'
'Bailey, Gwendolyn A.'
'Patrick, Brian O.'
'Orvig, Chris'
_publ_section_title
;
 3-Hydroxy-4-pyridinone derivatives as metal ion and amyloid binding
 agents.
;
_journal_issue                   2
_journal_name_full               'Metallomics : integrated biometal science'
_journal_page_first              249
_journal_page_last               262
_journal_paper_doi               10.1039/c3mt00135k
_journal_volume                  6
_journal_year                    2014
_chemical_formula_sum            'C13 H12 O3'
_chemical_formula_weight         216.23
_chemical_name_systematic
;
?
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   12.1889(5)
_cell_length_b                   8.9564(4)
_cell_length_c                   20.1062(9)
_cell_measurement_reflns_used    8669
_cell_measurement_temperature    100.0(2)
_cell_measurement_theta_max      30.03
_cell_measurement_theta_min      2.63
_cell_volume                     2194.97(17)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.0(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_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  0.0323
_diffrn_reflns_av_sigmaI/netI    0.0220
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            20285
_diffrn_reflns_theta_full        30.05
_diffrn_reflns_theta_max         30.05
_diffrn_reflns_theta_min         2.03
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  0.995
_exptl_absorpt_correction_T_min  0.909
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, Sheldrick (2008)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.309
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       irregular
_exptl_crystal_F_000             912
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.392
_refine_diff_density_min         -0.208
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         3208
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.0520
_refine_ls_R_factor_gt           0.0382
_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)+(0.0482P)²+0.8110P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0942
_refine_ls_wR_factor_ref         0.1022
_reflns_number_gt                2586
_reflns_number_total             3208
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            c3mt00135k.txt
_cod_data_source_block           co417
_cod_original_sg_symbol_H-M      'P bca'
_cod_database_code               1513741
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'
'-x, -y, -z'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'
'x-1/2, y, -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
O2 O 0.25909(6) 0.13267(9) 0.44782(4) 0.01813(17) Uani 1 1 d .
O3 O 0.14411(6) 0.09626(9) 0.61262(4) 0.01954(17) Uani 1 1 d .
O1 O 0.04134(7) 0.22828(9) 0.42852(4) 0.02326(19) Uani 1 1 d .
C11 C 0.42321(10) 0.17281(13) 0.22410(6) 0.0243(2) Uani 1 1 d .
H11 H 0.4630 0.2048 0.1861 0.029 Uiso 1 1 calc R
C12 C 0.32004(10) 0.23167(13) 0.23734(6) 0.0258(2) Uani 1 1 d .
H12 H 0.2897 0.3051 0.2087 0.031 Uiso 1 1 calc R
C13 C 0.26107(9) 0.18321(12) 0.29254(6) 0.0212(2) Uani 1 1 d .
H13 H 0.1904 0.2235 0.3012 0.025 Uiso 1 1 calc R
C8 C 0.30497(8) 0.07596(11) 0.33511(5) 0.0156(2) Uani 1 1 d .
C7 C 0.24056(9) 0.02460(12) 0.39461(5) 0.0195(2) Uani 1 1 d .
H7A H 0.1615 0.0193 0.3836 0.023 Uiso 1 1 calc R
H7B H 0.2654 -0.0758 0.4087 0.023 Uiso 1 1 calc R
C3 C 0.18163(8) 0.13011(11) 0.49763(5) 0.0149(2) Uani 1 1 d .
C2 C 0.21314(8) 0.08584(11) 0.55926(5) 0.0162(2) Uani 1 1 d .
C6 C 0.04152(9) 0.15046(12) 0.60293(5) 0.0192(2) Uani 1 1 d .
H6 H -0.0056 0.1586 0.6404 0.023 Uiso 1 1 calc R
C10 C 0.46785(9) 0.06705(12) 0.26670(6) 0.0222(2) Uani 1 1 d .
H10 H 0.5387 0.0274 0.2580 0.027 Uiso 1 1 calc R
C9 C 0.40910(9) 0.01866(12) 0.32228(5) 0.0180(2) Uani 1 1 d .
H9 H 0.4402 -0.0534 0.3514 0.022 Uiso 1 1 calc R
C4 C 0.07144(9) 0.18686(11) 0.48445(5) 0.0158(2) Uani 1 1 d .
C5 C 0.00262(9) 0.19319(12) 0.54357(5) 0.0183(2) Uani 1 1 d .
H5 H -0.0708 0.2280 0.5400 0.022 Uiso 1 1 calc R
C1 C 0.32318(9) 0.02639(14) 0.57765(6) 0.0241(2) Uani 1 1 d .
H1A H 0.3570 -0.0206 0.5387 0.036 Uiso 1 1 calc R
H1B H 0.3152 -0.0478 0.6132 0.036 Uiso 1 1 calc R
H1C H 0.3698 0.1084 0.5932 0.036 Uiso 1 1 calc R
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'
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
C3 O2 C7 114.58(8)
C6 O3 C2 118.66(8)
C10 C11 C12 119.70(10)
C10 C11 H11 120.2
C12 C11 H11 120.2
C11 C12 C13 120.13(11)
C11 C12 H12 119.9
C13 C12 H12 119.9
C12 C13 C8 120.44(10)
C12 C13 H13 119.8
C8 C13 H13 119.8
C9 C8 C13 119.35(10)
C9 C8 C7 120.69(9)
C13 C8 C7 119.96(10)
O2 C7 C8 107.43(8)
O2 C7 H7A 110.2
C8 C7 H7A 110.2
O2 C7 H7B 110.2
C8 C7 H7B 110.2
H7A C7 H7B 108.5
C2 C3 O2 118.38(9)
C2 C3 C4 121.87(9)
O2 C3 C4 119.54(9)
C3 C2 O3 121.52(9)
C3 C2 C1 125.88(10)
O3 C2 C1 112.58(9)
C5 C6 O3 123.84(10)
C5 C6 H6 118.1
O3 C6 H6 118.1
C11 C10 C9 120.30(10)
C11 C10 H10 119.8
C9 C10 H10 119.8
C8 C9 C10 120.08(10)
C8 C9 H9 120.0
C10 C9 H9 120.0
O1 C4 C5 123.94(10)
O1 C4 C3 122.75(9)
C5 C4 C3 113.29(9)
C6 C5 C4 120.80(10)
C6 C5 H5 119.6
C4 C5 H5 119.6
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
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O2 C3 1.3766(12)
O2 C7 1.4603(12)
O3 C6 1.3554(13)
O3 C2 1.3667(12)
O1 C4 1.2397(13)
C11 C10 1.3883(17)
C11 C12 1.3894(18)
C11 H11 0.9500
C12 C13 1.3916(16)
C12 H12 0.9500
C13 C8 1.3934(15)
C13 H13 0.9500
C8 C9 1.3931(15)
C8 C7 1.5031(14)
C7 H7A 0.9900
C7 H7B 0.9900
C3 C2 1.3566(14)
C3 C4 1.4603(14)
C2 C1 1.4896(15)
C6 C5 1.3401(15)
C6 H6 0.9500
C10 C9 1.3962(15)
C10 H10 0.9500
C9 H9 0.9500
C4 C5 1.4559(15)
C5 H5 0.9500
C1 H1A 0.9800
C1 H1B 0.9800
C1 H1C 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
C10 C11 C12 C13 -0.93(18)
C11 C12 C13 C8 0.27(17)
C12 C13 C8 C9 0.65(16)
C12 C13 C8 C7 179.93(10)
C3 O2 C7 C8 160.49(9)
C9 C8 C7 O2 96.01(11)
C13 C8 C7 O2 -83.26(12)
C7 O2 C3 C2 113.70(11)
C7 O2 C3 C4 -71.62(12)
O2 C3 C2 O3 172.62(9)
C4 C3 C2 O3 -1.93(15)
O2 C3 C2 C1 -5.55(16)
C4 C3 C2 C1 179.90(10)
C6 O3 C2 C3 0.87(14)
C6 O3 C2 C1 179.25(9)
C2 O3 C6 C5 0.88(15)
C12 C11 C10 C9 0.65(17)
C13 C8 C9 C10 -0.92(15)
C7 C8 C9 C10 179.80(10)
C11 C10 C9 C8 0.28(16)
C2 C3 C4 O1 179.75(10)
O2 C3 C4 O1 5.26(15)
C2 C3 C4 C5 1.25(14)
O2 C3 C4 C5 -173.24(9)
O3 C6 C5 C4 -1.49(17)
O1 C4 C5 C6 -178.07(10)
C3 C4 C5 C6 0.40(14)
