#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/37/1513738.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_1513738
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            'C14 H12 N2 O3'
_chemical_formula_weight         256.26
_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                82.538(4)
_cell_angle_beta                 83.524(4)
_cell_angle_gamma                61.968(4)
_cell_formula_units_Z            2
_cell_length_a                   7.1289(9)
_cell_length_b                   7.1436(10)
_cell_length_c                   13.037(2)
_cell_measurement_reflns_used    4563
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.36
_cell_measurement_theta_min      3.16
_cell_volume                     580.05(14)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.990
_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  0.0350
_diffrn_reflns_av_sigmaI/netI    0.0536
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            10244
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         28.37
_diffrn_reflns_theta_min         3.16
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_T_max  0.998
_exptl_absorpt_correction_T_min  0.936
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.467
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             268
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.293
_refine_diff_density_min         -0.371
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     185
_refine_ls_number_reflns         2878
_refine_ls_number_restraints     290
_refine_ls_restrained_S_all      0.996
_refine_ls_R_factor_all          0.0694
_refine_ls_R_factor_gt           0.0435
_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)+(0.0403P)²+0.1937P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0951
_refine_ls_wR_factor_ref         0.1063
_reflns_number_gt                2095
_reflns_number_total             2878
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            c3mt00135k.txt
_cod_data_source_block           co402
_cod_original_cell_volume        580.08(14)
_cod_database_code               1513738
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
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.22470(14) 0.21596(15) 0.30895(8) 0.0194(2) Uani 1 1 d U . .
H1A H 0.1653 0.3424 0.3476 0.029 Uiso 1 1 calc R . .
H1B H 0.1274 0.1528 0.3180 0.029 Uiso 1 1 calc R . .
H1C H 0.2431 0.2566 0.2352 0.029 Uiso 1 1 calc R . .
C2 C 0.43641(13) 0.05673(14) 0.34878(7) 0.0138(2) Uani 1 1 d U . .
C3 C 0.47463(13) -0.14121(14) 0.39469(7) 0.0137(2) Uani 1 1 d U . .
C4 C 0.67647(14) -0.29298(14) 0.43440(7) 0.0136(2) Uani 1 1 d U . .
C5 C 0.83421(13) -0.22308(14) 0.42407(7) 0.0148(2) Uani 1 1 d U . .
H5 H 0.9716 -0.3153 0.4483 0.018 Uiso 1 1 calc R . .
C6 C 0.79049(14) -0.02537(14) 0.37979(7) 0.0145(2) Uani 1 1 d U . .
H6 H 0.8984 0.0182 0.3749 0.017 Uiso 1 1 calc R . .
C7 C 0.57486(14) 0.31734(14) 0.28865(7) 0.0160(2) Uani 1 1 d U . .
H7A H 0.6549 0.3690 0.3244 0.019 Uiso 1 1 calc R A 1
H7B H 0.4228 0.4242 0.2925 0.019 Uiso 1 1 calc R A 1
N1 N 0.59840(11) 0.11270(11) 0.34214(6) 0.01350(17) Uani 1 1 d U B .
C8 C 0.65448(15) 0.29614(15) 0.17812(8) 0.0200(2) Uani 1 1 d DU B 1
C9 C 0.83283(15) 0.28777(14) 0.03429(8) 0.0187(2) Uani 1 1 d U B 1
C10 C 0.97614(17) 0.29413(16) -0.04560(8) 0.0268(3) Uani 1 1 d U B 1
H10 H 1.0873 0.3259 -0.0348 0.032 Uiso 1 1 calc R B 1
C11 C 0.94882(18) 0.25177(16) -0.14181(8) 0.0328(3) Uani 1 1 d U B 1
H11 H 1.0424 0.2568 -0.1988 0.039 Uiso 1 1 calc R B 1
C12 C 0.78862(19) 0.20215(16) -0.15730(9) 0.0347(3) Uani 1 1 d U B 1
H12 H 0.7757 0.1738 -0.2246 0.042 Uiso 1 1 calc R B 1
C13 C 0.64655(17) 0.19277(16) -0.07716(9) 0.0299(3) Uani 1 1 d U B 1
H13 H 0.5372 0.1578 -0.0873 0.036 Uiso 1 1 calc R B 1
C14 C 0.67422(15) 0.23747(15) 0.01806(8) 0.0194(2) Uani 1 1 d U B 1
N2 N 0.8146(8) 0.3273(10) 0.1424(3) 0.0151(5) Uani 0.714(7) 1 d PDU B 1
O3 O 0.5643(5) 0.2356(5) 0.1106(3) 0.0194(6) Uani 0.714(7) 1 d PDU B 1
O1 O 0.70368(10) -0.47413(10) 0.47637(5) 0.01980(16) Uani 1 1 d U . .
O2 O 0.31452(10) -0.19690(10) 0.40549(5) 0.01701(16) Uani 1 1 d U . .
O3B O 0.8212(17) 0.319(2) 0.1295(7) 0.0194(6) Uani 0.286(7) 1 d PDU B 2
N2B N 0.5451(19) 0.260(2) 0.1175(10) 0.0151(5) Uani 0.286(7) 1 d PDU B 2
H2O H 0.3512(18) -0.321(2) 0.4471(9) 0.050(4) 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 118.23(8)
C3 C2 C1 122.78(8)
N1 C2 C1 118.96(8)
O2 C3 C2 119.23(8)
O2 C3 C4 117.85(7)
C2 C3 C4 122.91(8)
O1 C4 C5 124.32(8)
O1 C4 C3 120.48(8)
C5 C4 C3 115.20(8)
C6 C5 C4 120.48(8)
C6 C5 H5 119.8
C4 C5 H5 119.8
C5 C6 N1 122.58(8)
C5 C6 H6 118.7
N1 C6 H6 118.7
N1 C7 C8 111.71(7)
N1 C7 H7A 109.3
C8 C7 H7A 109.3
N1 C7 H7B 109.3
C8 C7 H7B 109.3
H7A C7 H7B 107.9
C6 N1 C2 120.59(7)
C6 N1 C7 117.60(7)
C2 N1 C7 121.70(7)
N2 C8 O3 117.0(2)
N2 C8 C7 122.0(2)
O3 C8 C7 121.0(2)
C14 C9 C10 121.20(10)
C14 C9 N2 108.34(16)
C10 C9 N2 130.47(17)
C11 C10 C9 116.53(10)
C11 C10 H10 121.7
C9 C10 H10 121.7
C10 C11 C12 121.78(10)
C10 C11 H11 119.1
C12 C11 H11 119.1
C11 C12 C13 121.86(11)
C11 C12 H12 119.1
C13 C12 H12 119.1
C14 C13 C12 115.75(11)
C14 C13 H13 122.1
C12 C13 H13 122.1
O3 C14 C13 129.05(15)
O3 C14 C9 108.05(14)
C13 C14 C9 122.87(10)
C8 N2 C9 102.0(3)
C14 O3 C8 104.5(2)
C3 O2 H2O 111.0(7)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.5004(12)
C1 H1A 0.9800
C1 H1B 0.9800
C1 H1C 0.9800
C2 C3 1.3736(12)
C2 N1 1.3796(11)
C3 O2 1.3626(10)
C3 C4 1.4388(12)
C4 O1 1.2711(10)
C4 C5 1.4171(12)
C5 C6 1.3565(12)
C5 H5 0.9500
C6 N1 1.3584(11)
C6 H6 0.9500
C7 N1 1.4773(11)
C7 C8 1.4877(13)
C7 H7A 0.9900
C7 H7B 0.9900
C8 N2 1.289(4)
C8 O3 1.365(3)
C9 C14 1.3813(13)
C9 C10 1.3863(13)
C9 N2 1.453(4)
C10 C11 1.3827(15)
C10 H10 0.9500
C11 C12 1.3864(16)
C11 H11 0.9500
C12 C13 1.3888(16)
C12 H12 0.9500
C13 C14 1.3782(14)
C13 H13 0.9500
C14 O3 1.364(5)
O2 H2O 0.914(12)
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 177.62(8)
C1 C2 C3 O2 -0.37(14)
N1 C2 C3 C4 -1.02(14)
C1 C2 C3 C4 -179.00(9)
O2 C3 C4 O1 1.25(13)
C2 C3 C4 O1 179.90(9)
O2 C3 C4 C5 -177.91(8)
C2 C3 C4 C5 0.74(13)
O1 C4 C5 C6 -178.83(9)
C3 C4 C5 C6 0.29(13)
C4 C5 C6 N1 -1.05(14)
C5 C6 N1 C2 0.78(13)
C5 C6 N1 C7 -175.53(8)
C3 C2 N1 C6 0.26(13)
C1 C2 N1 C6 178.32(8)
C3 C2 N1 C7 176.41(8)
C1 C2 N1 C7 -5.52(12)
C8 C7 N1 C6 83.48(10)
C8 C7 N1 C2 -92.78(10)
N1 C7 C8 N2 -116.2(3)
N1 C7 C8 O3 61.6(2)
C14 C9 C10 C11 1.21(14)
N2 C9 C10 C11 -178.8(3)
C9 C10 C11 C12 -1.00(14)
C10 C11 C12 C13 0.16(16)
C11 C12 C13 C14 0.49(15)
C12 C13 C14 O3 -178.2(2)
C12 C13 C14 C9 -0.28(14)
C10 C9 C14 O3 177.67(17)
N2 C9 C14 O3 -2.3(4)
C10 C9 C14 C13 -0.60(14)
N2 C9 C14 C13 179.4(3)
O3 C8 N2 C9 1.7(4)
C7 C8 N2 C9 179.59(16)
C14 C9 N2 C8 0.4(4)
C10 C9 N2 C8 -179.52(16)
C13 C14 O3 C8 -178.77(12)
C9 C14 O3 C8 3.1(2)
N2 C8 O3 C14 -3.1(3)
C7 C8 O3 C14 178.93(12)
