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#$Date: 2016-03-21 16:46:47 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178754 $
#$URL: svn://www.crystallography.net/cod/cif/4/10/08/4100812.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_4100812
loop_
_publ_author_name
'Paola Gilli'
'Valerio Bertolasi'
'Loretta Pretto'
'Valeria Ferretti'
'Gastone Gilli'
_publ_section_title
;
Covalent versus Electrostatic Nature of the Strong Hydrogen Bond:
Discrimination among Single, Double, and Asymmetric Single-Well Hydrogen
Bonds by Variable-Temperature X-ray Crystallographic Methods in β-Diketone
Enol RAHB Systems
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              3845
_journal_page_last               3855
_journal_paper_doi               10.1021/ja030213z
_journal_volume                  126
_journal_year                    2004
_chemical_formula_moiety         'C16 H13 N O5'
_chemical_formula_sum            'C16 H13 N O5'
_chemical_formula_weight         299.27
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_cell_angle_alpha                90.00
_cell_angle_beta                 101.273(1)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.2913(1)
_cell_length_b                   16.0408(3)
_cell_length_c                   12.3333(2)
_cell_measurement_temperature    295
_cell_volume                     1414.65(4)
_diffrn_ambient_temperature      295
_exptl_crystal_density_diffrn    1.405
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4100812
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O -0.1355(2) 0.97416(9) 0.71024(11) 0.0738(4) Uani 1 1 d . . .
O2 O -0.1542(2) 1.12604(9) 0.69215(12) 0.0773(4) Uani 1 1 d . . .
O3 O 0.0170(2) 1.50255(8) 0.71380(13) 0.0805(4) Uani 1 1 d . . .
O4 O -0.13978(19) 1.41393(8) 0.60110(11) 0.0704(4) Uani 1 1 d . . .
O5 O 0.2739(2) 0.68500(8) 1.00740(11) 0.0777(4) Uani 1 1 d . . .
N1 N -0.0339(2) 1.43146(9) 0.68789(13) 0.0576(4) Uani 1 1 d . . .
C1 C -0.0042(2) 0.98180(10) 0.79624(13) 0.0506(4) Uani 1 1 d . . .
C2 C 0.0598(2) 1.06175(10) 0.83217(13) 0.0511(4) Uani 1 1 d . . .
C3 C -0.0176(2) 1.13208(10) 0.77725(12) 0.0513(4) Uani 1 1 d . . .
C4 C 0.0461(2) 1.21820(10) 0.80781(12) 0.0486(4) Uani 1 1 d . . .
C5 C 0.1746(3) 1.23628(12) 0.90400(14) 0.0622(5) Uani 1 1 d . . .
C6 C 0.2333(3) 1.31714(13) 0.92901(16) 0.0726(6) Uani 1 1 d . . .
C7 C 0.1650(3) 1.38148(12) 0.85907(15) 0.0627(5) Uani 1 1 d . . .
C8 C 0.0373(2) 1.36312(10) 0.76436(13) 0.0499(4) Uani 1 1 d . . .
C9 C -0.0235(2) 1.28344(10) 0.73706(13) 0.0488(4) Uani 1 1 d . . .
C10 C 0.0702(2) 0.90456(10) 0.85171(12) 0.0478(4) Uani 1 1 d . . .
C11 C 0.0120(2) 0.82798(10) 0.80246(14) 0.0529(4) Uani 1 1 d . . .
C12 C 0.0766(2) 0.75373(11) 0.85133(14) 0.0559(4) Uani 1 1 d . . .
C13 C 0.2021(3) 0.75436(10) 0.95153(14) 0.0550(4) Uani 1 1 d . . .
C14 C 0.2622(3) 0.82979(11) 1.00162(14) 0.0579(4) Uani 1 1 d . . .
C15 C 0.1968(2) 0.90393(11) 0.95248(13) 0.0520(4) Uani 1 1 d . . .
C16 C 0.2210(5) 0.60593(14) 0.9583(2) 0.0876(8) Uani 1 1 d . . .
H1 H -0.172(5) 1.050(2) 0.683(2) 0.156(13) Uani 1 1 d . . .
H2 H 0.156(3) 1.0672(11) 0.8929(16) 0.058(5) Uiso 1 1 d . . .
H5 H 0.225(3) 1.1928(13) 0.9538(17) 0.069(5) Uiso 1 1 d . . .
H6 H 0.320(3) 1.3329(15) 0.993(2) 0.092(7) Uiso 1 1 d . . .
H7 H 0.200(3) 1.4391(14) 0.8720(19) 0.082(6) Uiso 1 1 d . . .
H9 H -0.111(3) 1.2729(12) 0.6700(18) 0.067(5) Uiso 1 1 d . . .
H11 H -0.071(3) 0.8272(13) 0.7366(17) 0.074(6) Uiso 1 1 d . . .
H12 H 0.035(3) 0.7020(12) 0.8137(16) 0.066(5) Uiso 1 1 d . . .
H14 H 0.349(3) 0.8312(13) 1.0717(18) 0.074(6) Uiso 1 1 d . . .
H15 H 0.239(2) 0.9563(13) 0.9905(16) 0.063(5) Uiso 1 1 d . . .
H161 H 0.087(5) 0.5989(19) 0.953(3) 0.123(11) Uiso 1 1 d . . .
H162 H 0.257(4) 0.5997(17) 0.885(3) 0.110(9) Uiso 1 1 d . . .
H163 H 0.290(4) 0.562(2) 1.006(3) 0.118(9) Uiso 1 1 d . . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.288(2) . ?
O1 H1 1.28(4) . ?
O2 C3 1.302(2) . ?
O2 H1 1.22(4) . ?
O3 N1 1.2225(19) . ?
O4 N1 1.2237(19) . ?
O5 C13 1.359(2) . ?
O5 C16 1.426(3) . ?
N1 C8 1.473(2) . ?
C1 C2 1.407(2) . ?
C1 C10 1.467(2) . ?
C2 H2 0.93(2) . ?
C2 C3 1.379(2) . ?
C3 C4 1.482(2) . ?
C4 C5 1.391(2) . ?
C4 C9 1.393(2) . ?
C5 H5 0.95(2) . ?
C5 C6 1.382(3) . ?
C6 H6 0.95(3) . ?
C6 C7 1.375(3) . ?
C7 H7 0.96(2) . ?
C7 C8 1.376(2) . ?
C8 C9 1.373(2) . ?
C9 H9 0.96(2) . ?
C10 C15 1.396(2) . ?
C10 C11 1.399(2) . ?
C11 H11 0.91(2) . ?
C11 C12 1.376(2) . ?
C12 H12 0.97(2) . ?
C12 C13 1.387(2) . ?
C13 C14 1.390(2) . ?
C14 H14 0.97(2) . ?
C14 C15 1.377(2) . ?
C15 H15 0.98(2) . ?
C16 H161 0.98(3) . ?
C16 H162 0.99(3) . ?
C16 H163 1.00(3) . ?
